Substituted cyclic amides and their use as herbicides

Information

  • Patent Grant
  • 11180453
  • Patent Number
    11,180,453
  • Date Filed
    Friday, May 15, 2020
    4 years ago
  • Date Issued
    Tuesday, November 23, 2021
    3 years ago
Abstract
Disclosed are compounds of Formula 1, N-oxides of the compounds and salts of the compounds and N-oxides:
Description
FIELD OF THE DISCLOSURE

This disclosure relates to certain pyrrolidinones, N-oxides thereof, and salts of the pyrrolidinones and N-oxides; compositions comprising such pyrrolidinones, N-oxides and salts; processes for making such pyrrolidinones, N-oxides, salts and compositions; and methods for using such pyrrolidinones, N-oxides, salts and compositions to control undesirable vegetation.


BACKGROUND

The control of undesired vegetation is extremely important in achieving high crop efficiency. Achievement of selective control of the growth of weeds especially in such useful crops as rice, soybean, sugar beet, maize, potato, wheat, barley, tomato and plantation crops, among others, is very desirable. Unchecked weed growth in such useful crops can cause significant reduction in productivity and thereby result in increased costs to the consumer. The control of undesired vegetation in noncrop areas is also important. Many products are commercially available for these purposes, but the need continues for new compounds that are more effective, less costly, less toxic, environmentally safer or have different sites of action.


SUMMARY

This disclosure relates, in part, to compounds of Formula 1 (including all stereoisomers), N-oxides of such compounds, and salts of such compounds and N-oxides:




embedded image



wherein

    • Q1 is a phenyl ring or a naphthalenyl ring system, each ring or ring system optionally substituted with up to 5 substituents independently selected from R7; or a 4- to 7-membered heterocyclic ring; or an 8- to 10-membered bicyclic ring system, each ring or ring system containing ring members selected from carbon atoms and 1 to 5 heteroatoms independently selected from up to 2 O, up to 2 S and up to 5 N atoms, wherein up to 3 carbon ring members are independently selected from C(═O) and C(═S), and the sulfur atom ring members are independently selected from S(═O)u(═NR8)v, each ring or ring system optionally substituted with up to 5 substituents independently selected from R7 on carbon atom ring members and selected from R9 on nitrogen atom ring members; or
    • Q1 is C2-C10 alkenyl, C2-C10 alkynyl, C2-C10 haloalkenyl, C2-C10 haloalkynyl, C4-C10 cycloalkenyl, C4-C10 halocycloalkenyl, C2-C8 alkylcarbonyl or C2-C8 alkoxyalkyl;
    • Q2 is a phenyl ring or a naphthalenyl ring system, each ring or ring system optionally substituted with up to 5 substituents independently selected from R10; or a 4- to 7-membered heterocyclic ring; or an 8- to 10-membered bicyclic ring system, each ring or ring system containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 5 N atoms, wherein up to 3 carbon ring members are independently selected from C(═O) and C(═S), and the sulfur atom ring members are independently selected from S(═O)u(═NR8)v, each ring or ring system optionally substituted with up to 5 substituents independently selected from R10 on carbon atom ring members and selected from R11 on nitrogen atom ring members; or
    • Q2 is C2-C10 alkenyl, C2-C10 alkynyl, C2-C10 haloalkenyl, C2-C10 haloalkynyl, C4-C10 cycloalkenyl, C4-C10 halocycloalkenyl, C2-C8 alkylcarbonyl or C2-C8 alkoxyalkyl;
    • J is —CR2R3—, —NR2a— or —O—;
    • Y1 and Y2 are each independently O, S or NR12;
    • R1 is H, hydroxy, amino, cyano, formyl, C3-C8 alkylcarbonylalkyl, —C(C1-C4 alkyl)=N—O(C1-C4 alkyl), —C(O)NH2, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C2-C6 cyanoalkyl, C3-C6 cycloalkyl, C3-C8 cycloalkenyl, C4-C8 cycloalkylalkyl, C2-C8 alkoxyalkyl, C3-C8 alkoxyalkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 haloalkenylalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C10 cycloalkylcarbonyl, C5-C10 cycloalkylcarbonylalkyl, C2-C8 alkoxycarbonyl, C2-C8 haloalkoxycarbonyl, C4-C10 cycloalkoxycarbonyl, C2-C8 alkylaminocarbonyl, C3-C10 dialkylaminocarbonyl, C4-C10 cycloalkylaminocarbonyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3-C8 cycloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C3-C8 cycloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C1-C6 alkylaminosulfonyl, C2-C8 dialkylaminosulfonyl, C3-C10 trialkylsilyl; or —CPh=N—O(C1-C4 alkyl), each optionally substituted on ring members with up to 5 substituents independently selected from R13; or G1; or W1G1;
    • R2 and R3 are each independently H, halogen, hydroxy, C1-C4 alkyl, C1-C4 haloalkyl or C1-C4 alkoxy; or
    • R2 and R3 are taken together with the carbon atom to which they are bonded to form a C3-C7 cycloalkyl ring;
    • R2a is C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl or C1-C6 alkoxy; or
    • R1 and R2a are taken together as C3-C6 alkylene or —CH2OCH2—;
    • R4 and R5 are each independently H, halogen, hydroxy, C1-C4 alkoxy, C1-C4 haloalkyl or C1-C4 alkyl;
    • R6 is H, hydroxy, amino, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C10 cycloalkylcarbonyl, C2-C8 alkoxycarbonyl, C2-C8 haloalkoxycarbonyl, C4-C10 cycloalkoxycarbonyl, C2-C8 alkylaminocarbonyl, C3-C10 dialkylaminocarbonyl, C4-C10 cycloalkylaminocarbonyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3-C8 cycloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C3-C8 cycloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C1-C6 alkylaminosulfonyl, C2-C8 dialkylaminosulfonyl or C3-C10 trialkylsilyl or G1; or
    • R6 and Q2 are taken together with the nitrogen atom to which they are both bonded to form an 8- to 10-membered bicyclic ring system, each ring or ring system containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 4 N atoms, wherein up to 3 carbon ring members are independently selected from C(═O) and C(═S), and the sulfur atom ring members are independently selected from S(═O)u(═NR8)v, each ring or ring system optionally substituted with up to 5 substituents independently selected from R7 on carbon atom ring members and selected from R9 on nitrogen atom ring members;
    • each R7 and R10 is independently halogen, hydroxy, cyano, nitro, amino, C1-C8 alkyl, C1-C8 cyanoalkyl, C1-C8 cyanoalkoxy, C1-C8 haloalkyl, C1-C8 hydroxyalkyl, C1-C8 nitroalkyl, C2-C8 alkenyl, C2-C8 haloalkenyl, C2-C8 nitroalkenyl, C2-C8 alkynyl, C2-C8 haloalkynyl, C2-C8 alkoxyalkyl, C3-C8 alkoxyalkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 haloalkoxyhaloalkoxy, C3-C6 cycloalkyl, cyclopropylmethyl, 1-methylcyclopropyl, 2-methylcyclopropyl, C4-C10 cycloalkylalkyl, C4-C10 halocycloalkylalkyl, C5-C12 alkylcycloalkylalkyl, C5-C12 cycloalkylalkenyl, C5-C12 cycloalkylalkynyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C4-C10 alkylcycloalkyl, C6-C12 cycloalkylcycloalkyl, C3-C8 cycloalkenyl, C3-C8 halocycloalkenyl, C2-C8 haloalkoxyalkoxy, C2-C8 alkoxyalkoxy, C4-C10 cycloalkoxyalkyl, C3-C10 alkoxyalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylamino, C2-C8 dialkylamino, C2-C8 halodialkylamino, C2-C8 alkylaminoalkyl, C2-C8 haloalkylaminoalkyl, C4-C10 cycloalkylaminoalkyl, C3-C10 dialkylaminoalkyl, —CHO, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C10 cycloalkylcarbonyl, —C(═O)OH, C2-C8 alkoxycarbonyl, C2-C8 haloalkoxycarbonyl, C4-C10 cycloalkoxycarbonyl, C5-C12 cycloalkylalkoxycarbonyl, —C(═O)NH2, C2-C8 alkylaminocarbonyl, C4-C10 cycloalkylaminocarbonyl, C3-C10 dialkylaminocarbonyl, C1-C8 alkoxy, C1-C8 haloalkoxy, C2-C8 alkoxyalkoxy, C2-C8 alkenyloxy, C2-C8 haloalkenyloxy, C3-C8 alkynyloxy, C3-C8 haloalkynyloxy, C3-C8 cycloalkoxy, C3-C8 halocycloalkoxy, C4-C10 cycloalkylalkoxy, C3-C10 alkylcarbonylalkoxy, C2-C8 alkylcarbonyloxy, C2-C8 haloalkylcarbonyloxy, C4-C10 cycloalkylcarbonyloxy, C1-C8 alkylsulfonyloxy, C1-C8 haloalkylsulfonyloxy, C1-C8 alkylthio, C1-C8 haloalkylthio, C3-C8 cycloalkylthio, C1-C8 alkylsulfinyl, C1-C8 haloalkylsulfinyl, C1-C8 alkylsulfonyl, C1-C8 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, formylamino, C2-C8 alkylcarbonylamino, C2-C8 haloalkylcarbonylamino, C3-C8 cycloalkylamino, C2-C8 alkoxycarbonylamino, C1-C6 alkylsulfonylamino, C1-C6 haloalkylsulfonylamino, —SF5, —SCN, SO2NH2, C3-C12 trialkylsilyl, C4-C12 trialkylsilylalkyl or C4-C12 trialkylsilylalkoxy; or G2; or
    • each R7 is independently R26S(═O)═N—, R26S(═O)2NR25—C(═O)—, R26(R25N═)qS(═O)p—, wherein the free bond projecting to the right indicates the connecting point to Q1; or
    • each R10 is independently R17ON=CR17a—, (R18)2C═NO—, (R19)2NN═CR17a—, (R18)2C═NNR20a—, R20N=CR17a—, (R18)2C═N—, R17ON=CR17aC(R23b)2—, (R18)2C═NOC(R24a)2—, R26S(═O)═N—, R26S(═O)2NR25—C(═O)— or R26(R25N═)qS(═O)p—, wherein the free bond projecting to the right indicates the connecting point to Q2;
    • each R8 is independently H, cyano, C2-C3 alkylcarbonyl or C2-C3 haloalkylcarbonyl;
    • each R9 and R11 is independently cyano, C1-C3 alkyl, C1-C8 hydroxyalkyl, C2-C3 alkenyl, C2-C3 alkynyl, C3-C6 cycloalkyl, C2-C3 alkoxyalkyl, C1-C3 alkoxy, C2-C3 alkylcarbonyl, C2-C3 alkoxycarbonyl, C2-C3 alkylaminoalkyl or C3-C4 dialkylaminoalkyl;
    • each R12 is independently H, cyano, hydroxy, CHO, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C2-C6 alkylcarbonyl, C2-C6 haloalkylcarbonyl, —(C═O)CH3 or —(C═O)CF3;
    • each G1 is independently phenyl; or a 5- or 6-membered heterocyclic ring, each optionally substituted on ring members with up to 5 substituents independently selected from R13;
    • each G2 is independently phenyl, phenylmethyl (i.e. benzyl), pyridinylmethyl, phenylcarbonyl (i.e. benzoyl), phenoxy, phenylethynyl, phenylsulfonyl or a 5- or 6-membered heterocyclic ring, each optionally substituted on ring members with up to 5 substituents independently selected from R14;
    • W1 is C1-C3 alkylene, C2-C4 alkenylene, C2-C4 alkynylene, —(C1-C2 alkylene)C(═O)—, —C(═O)(C1-C2 alkylene)-, —CH2O—, —CH2NH—, —OCH2—, —NCH2—, —N—, —O—, —S—, —SO— or —SO2— wherein the free bond projecting to the left indicates the connecting point of W1 to N and the free bond projecting to the right indicates the connecting point of W1 to G1.
    • each R13 and R14 is independently halogen, cyano, hydroxy, amino, nitro, —CHO, —C(═O)OH, —C(═O)NH2, —SO2NH2, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C2-C8 alkoxycarbonyl, C4-C10 cycloalkoxycarbonyl, C5-C12 cycloalkylalkoxycarbonyl, C2-C8 alkylaminocarbonyl, C3-C10 dialkylaminocarbonyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C8 alkylcarbonyloxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C1-C6 alkylaminosulfonyl, C2-C8 dialkylaminosulfonyl, C3-C10 trialkylsilyl, C1-C6 alkylamino, C2-C8 dialkylamino, C2-C8 alkylcarbonylamino, C1-C6 alkylsulfonylamino, phenyl, pyridinyl or thienyl;
    • each R17 is independently H, C1-C6 alkyl, C3-C8 cycloalkyl, C4-C8 cycloalkylalkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C10 cycloalkylcarbonyl, C2-C8 alkoxycarbonyl, C2-C8 haloalkoxycarbonyl, C4-C10 cycloalkoxycarbonyl, C2-C8 alkylaminocarbonyl, C3-C10 dialkylaminocarbonyl, C4-C10 cycloalkylaminocarbonyl, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C3-C8 cycloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C1-C6 alkylaminosulfonyl, C2-C8 dialkylaminosulfonyl, C3-C10 trialkylsilyl or G1;
    • each R17a is independently H, C1-C6 alkyl, C3-C8 cycloalkyl, C4-C8 cycloalkylalkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3-C8 cycloalkylthio, C3-C10 trialkylsilyl or G1;
    • each R18 is independently H, hydroxy, C1-C6 alkyl, C3-C8 cycloalkyl, C4-C8 cycloalkylalkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C10 cycloalkylcarbonyl, C2-C8 alkoxycarbonyl, C2-C8 haloalkoxycarbonyl, C4-C10 cycloalkoxycarbonyl, C2-C8 alkylaminocarbonyl, C3-C10 dialkylaminocarbonyl, C4-C10 cycloalkylaminocarbonyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3-C8 cycloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C3-C8 cycloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C1-C6 alkylaminosulfonyl, C2-C8 dialkylaminosulfonyl, C3-C10 trialkylsilyl or G1;
    • each R19 is independently H, C1-C6 alkyl, C3-C8 cycloalkyl, C4-C8 cycloalkylalkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C10 cycloalkylcarbonyl, C2-C8 alkoxycarbonyl, C2-C8 haloalkoxycarbonyl, C4-C10 cycloalkoxycarbonyl, C2-C8 alkylaminocarbonyl, C3-C10 dialkylaminocarbonyl, C4-C10 cycloalkylaminocarbonyl, C1-C6 alkoxy, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C3-C8 cycloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C1-C6 alkylaminosulfonyl, C2-C8 dialkylaminosulfonyl, C3-C10 trialkylsilyl or G1;
    • each R20 is independently H, hydroxy, amino, C1-C6 alkyl, C3-C8 cycloalkyl, C4-C8 cycloalkylalkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C10 cycloalkylcarbonyl, C2-C8 alkoxycarbonyl, C2-C8 haloalkoxycarbonyl, C4-C10 cycloalkoxycarbonyl, C2-C8 alkylaminocarbonyl, C3-C10 dialkylaminocarbonyl, C4-C10 cycloalkylaminocarbonyl, C1-C6 alkoxy, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C3-C8 cycloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C1-C6 alkylaminosulfonyl, C2-C8 dialkylaminosulfonyl, C3-C10 trialkylsilyl or G1;
    • each R20a is independently H, C1-C6 alkyl, C3-C8 cycloalkyl, C4-C8 cycloalkylalkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C1-C6 alkoxy, C3-C10 trialkylsilyl or G1:
    • each R23b is independently H, halogen, cyano, hydroxy, C1-C4 alkyl, C3-C8 cycloalkyl, C4-C8 cycloalkylalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkoxyalkyl, C2-C4 alkylcarbonyl, C2-C4 alkoxycarbonyl or C3-C6 cycloalkyl;
    • each R24a is independently H, C1-C4 alkyl, C3-C8 cycloalkyl, C4-C8 cycloalkylalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkoxyalkyl, C2-C4 alkylcarbonyl, C2-C4 alkoxycarbonyl or C3-C6 cycloalkyl;
    • each R25 is independently H, cyano, C2-C3 alkylcarbonyl or C2-C3 haloalkylcarbonyl;
    • each R26 is independently H, C1-C6 alkyl, C3-C8 cycloalkyl, C4-C8 cycloalkylalkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C1-C6 alkoxy, C3-C10 trialkylsilyl or G1; and
    • each u and v are independently 0, 1 or 2 in each instance of S(═O)u(═NR8)v, provided that the sum of u and v is 0, 1 or 2;
    • each p and q are independently 0, 1 or 2 in each instance of R26(R25N═)qS(═O)p—, provided that the sum of u and v is 0, 1 or 2 and when p is 0, q is other than 1 or 2;
    • provided that
    • (a) the compound of Formula 1 is other than N-1H-benzotriazol-1-yl-2-oxo-4-phenyl-3-pyrrolidinecarboxamide;
    • (b) when Q1 comprises a 3-furanyl or 3-pyridinyl ring directly bonded to the remainder of Formula 1, then said ring is substituted with at least one substituent selected from R7;
    • (c) when Q1 is an unsubstituted phenyl ring, and Q2 comprises a phenyl ring directly bonded to the remainder of Formula 1, then said Q2 ring is substituted with R10 other than optionally substituted phenoxy or F at a 2-position, cyano or —CF3 at the 4-position and R5 is H or halogen;
    • (d) when Q1 is unsubstituted phenyl, and Q2 comprises a pyridinyl ring directly bonded to the remainder of Formula 1, then said pyridinyl ring is substituted with at least one substituent selected from R10;
    • (e) when Q1 is a phenyl ring substituted with 4-phenyl or 4-phenoxy, said Q1 ring is further substituted with and R7 substituent;
    • (f) when Q1 comprises a phenyl ring directly bonded to the remainder of Formula 1 and said ring is substituted with R7 at both ortho positions (relative to the bond to the remainder of Formula 1), then said ring is also independently substituted with R7 on at least one additional position;
    • (g) when Q1 is other than unsubstituted 1-naphthalenyl, then Q2 is other than 2,3-di-fluorophenyl or 2-CF3-phenyl;
    • (h) Q2 is other than optionally substituted 1H-pyrazol-5-yl; and
    • (i) when Q2 comprises a 1H-pyrazol-3-yl ring directly bonded to the remainder of Formula 1, said ring is substituted at the 1-position with R9.


This disclosure also relates, in part, to an agricultural (generally herbicidal) composition comprising such a compound, N-oxide or salt in a herbicidally effective amount and at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents, the composition optionally further comprising at least one additional active ingredient selected from the group consisting of other herbicides and herbicide safeners.


This disclosure also relates, in part, to processes for making the above-identified compounds, N-oxides, salts and compositions.


This disclosure also relates, in part, to methods for controlling the growth of undesired vegetation comprising contacting the vegetation or its environment with a herbicidally effective amount of an above-identified compound, N-oxide, salt or composition.







DETAILED DESCRIPTION

As used herein, the terms “comprises,” “comprising,” “includes,” “including,” “has,” “having,” “contains”, “containing,” “characterized by” or any other variation thereof, are intended to cover a non-exclusive inclusion, subject to any limitation explicitly indicated. For example, a composition, mixture, process or method that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such composition, mixture, process, or method.


The transitional phrase “consisting of” excludes any element, step, or ingredient not specified. If in the claim, such would close the claim to the inclusion of materials other than those recited except for impurities ordinarily associated therewith. When the phrase “consisting of” appears in a clause of the body of a claim, rather than immediately following the preamble, it limits only the element set forth in that clause; other elements are not excluded from the claim as a whole.


The transitional phrase “consisting essentially of” is used to define a composition, method that includes materials, steps, features, components, or elements, in addition to those literally disclosed, provided that these additional materials, steps, features, components, or elements do not materially affect the basic and novel characteristic(s) of the recited subject matter. The term “consisting essentially of” occupies a middle ground between “comprising” and “consisting of”.


Where applicants have defined subject matter with an open-ended term such as “comprising,” it should be readily understood that (unless otherwise stated) the description should be interpreted to also describe such subject matter using the terms “consisting essentially of” or “consisting of.”


Further, unless expressly stated to the contrary, “or” refers to an inclusive or and not to an exclusive or. For example, a condition A or B is satisfied by any one of the following: A is true (or present) and B is false (or not present), A is false (or not present) and B is true (or present), and both A and B are true (or present).


Also, the indefinite articles “a” and “an” are intended to be nonrestrictive regarding the number of instances (i.e. occurrences) of the element or component. Therefore “a” or “an” should be read to include one or at least one, and the singular word form of the element or component also includes the plural unless the number is obviously meant to be singular.


As referred to herein, the term “seedling”, used either alone or in a combination of words means a young plant developing from the embryo of a seed.


As referred to herein, the term “broadleaf” used either alone or in words such as “broadleaf weed” means dicot or dicotyledon, a term used to describe a group of angiosperms characterized by embryos having two cotyledons.


As used herein, the term “alkylating agent” refers to a chemical compound in which a carbon-containing radical is bound through a carbon atom to a leaving group such as halide or sulfonate, which is displaceable by bonding of a nucleophile to said carbon atom. Unless otherwise indicated, the term “alkylating” does not limit the carbon-containing radical to alkyl; the carbon-containing radicals in alkylating agents include the variety of carbon-bound substituent radicals specified for R1.


In the above recitations, the term “alkyl”, used either alone or in compound words such as “alkylthio” or “haloalkyl” includes straight-chain or branched alkyl, such as, methyl, ethyl, n-propyl, i-propyl, or the different butyl, pentyl or hexyl isomers. “Alkenyl” includes straight-chain or branched alkenes such as ethenyl, 1-propenyl, 2-propenyl, and the different butenyl, pentenyl and hexenyl isomers. “Alkenyl” also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl. “Alkynyl” includes straight-chain or branched alkynes such as ethynyl, 1-propynyl, 2-propynyl and the different butynyl, pentynyl and hexynyl isomers. “Alkynyl” can also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl. “Alkylene” denotes a straight-chain or branched alkanediyl. Examples of “alkylene” include CH2, CH2CH2, CH(CH3), CH2CH2CH2, CH2CH(CH3) and the different butylene, pentylene and hexylene isomers. “Alkenylene” denotes a straight-chain or branched alkenediyl. Examples of “alkenylene” include —CH═CH—, —CH2CH═CH—, —CH2CH═C(CH3)— and the different butyl, pentyl and hexyl isomers. “Alkynylene” denotes a straight-chain or branched alkynediyl. Examples of “alkynylene” include —C≡C—, —CH2C≡C—, —CH2CH2C≡C— and the different butyl and pentyl isomers


“Alkoxy” includes, for example, methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers. “Alkoxyalkyl” denotes alkoxy substitution on alkyl. Examples of “alkoxyalkyl” include CH3CH2, CH3OCH2CH2, CH3CH2OCH2, CH3CH2CH2CH2OCH2 and CH3CH2OCH2CH2. “Alkoxyalkoxyalkyl” denotes at least alkoxy substitution on the alkoxy moiety of alkoxyalkyl moiety. Examples of “alkoxyalkoxyalkyl” include CH3OCH2OCH2—, CH3CH2O(CH3)CHOCH2— and (CH3)2CHOCH2—. “Alkoxyalkoxy” denotes alkoxy substitution on alkoxy. “Alkenyloxy” includes straight-chain or branched alkenyloxy moieties. Examples of “alkenyloxy” include H2C═CHCH2O, (CH3)2C═CHCH2, (CH3)CH═CHCH2, (CH3)CH═C(CH3)CH2O and CH2═CHCH2CH2O. “Alkynyloxy” includes straight-chain or branched alkynyloxy moieties. Examples of “alkynyloxy” include HC≡CCH2O, CH3C≡CCH2O and CH3C≡CCH2CH2O. “Alkylthio” includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, and the different propylthio, butylthio, pentylthio and hexylthio isomers. “Alkylsulfinyl” includes both enantiomers of an alkylsulfinyl group. Examples of “alkylsulfinyl” include CH3S(O)—, CH3CH2S(O)—, CH3CH2CH2S(O)—, (CH3)2CHS(O)— and the different butylsulfinyl, pentylsulfinyl and hexylsulfinyl isomers. Examples of “alkylsulfonyl” include CH3S(O)2—, CH3CH2S(O)2—, CH3CH2CH2S(O)2—, (CH3)2CHS(O)2—, and the different butylsulfonyl, pentylsulfonyl and hexylsulfonyl isomers. “Alkylthioalkyl” denotes alkylthio substitution on alkyl. Examples of “alkylthioalkyl” include CH3SCH2, CH3SCH2CH2, CH3CH2SCH2, CH3CH2CH2CH2SCH2 and CH3CH2SCH2CH2. “Alkylsulfinylalkyl” denotes alkylsulfinyl substitution on alkyl. Examples of “alkylsulfinylalkyl” include CH3S(═O)CH2, CH3S(═O)CH2CH2, CH3CH2S(═O)CH2 and CH3CH2S(═O)CH2CH2. “Alkylsulfonylalkyl” denotes alkylsulfonyl substitution on alkyl. Examples of “alkylsulfonylalkyl” include CH3S(═O)2CH2, CH3S(═O)2CH2CH2, CH3CH2S(═O)2CH2 and CH3CH2S(═O)2CH2CH2. “Alkylamino”, “dialkylamino”, and the like, are defined analogously to the above examples. Examples of “alkylaminoalkyl” include CH3NHCH2—, (CH3)2CHNHCH2— and CH3NHCH(CH3)—. Examples of “dialkylaminoalkyl” include (CH3)2NCH2—, (CH3)2NC(CH3)H— and (CH3)(CH3)NCH2—. Examples of “dialkylaminocarbonyl” include (CH3)2NC(O)—. Examples of “dialkylaminosulfonyl” include (CH3)2NS(O)2—. The term “alkoxycarbonylamino” denotes a straight-chain or branched alkoxy moieties bonded to a C(═O) moiety of carbonylamino group. Examples of “alkoxycarbonylamino” include CH3OC(═O)NH— and CH3CH2OC(═O)NH—.


“Cycloalkyl” includes, for example, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. The term “alkylcycloalkyl” denotes alkyl substitution on a cycloalkyl moiety and includes, for example, ethylcyclopropyl, i-propylcyclobutyl, 3-methylcyclopentyl and 4-methylcyclohexyl. The term “cycloalkylalkyl” denotes cycloalkyl substitution on an alkyl moiety. Examples of “cycloalkylalkyl” include cyclopropylmethyl, cyclopentylethyl, and other cycloalkyl moieties bonded to straight-chain or branched alkyl groups. The term “cycloalkoxy” denotes cycloalkyl linked through an oxygen atom such as cyclopentyloxy and cyclohexyloxy. “Cycloalkylalkoxy” denotes cycloalkylalkyl linked through an oxygen atom attached to the alkyl chain. Examples of “cycloalkylalkoxy” include cyclopropylmethoxy, cyclopentylethoxy, and other cycloalkyl moieties bonded to straight-chain or branched alkoxy groups. “Cycloalkenyl” includes groups such as cyclopentenyl and cyclohexenyl as well as groups with more than one double bond such as 1,3- and 1,4-cyclohexadienyl.


The term “halogen”, either alone or in compound words such as “haloalkyl”, or when used in descriptions such as “alkyl substituted with halogen” includes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as “haloalkyl”, or when used in descriptions such as “alkyl substituted with halogen” said alkyl may be partially or fully substituted with halogen atoms which may be the same or different. Examples of “haloalkyl” or “alkyl substituted with halogen” include F3C, ClCH2, CF3CH2 and CF3CCl2. The terms “halocycloalkyl”, “haloalkoxy”, “haloalkylthio”, “haloalkenyl”, “haloalkynyl”, “haloalkenyloxy”, “haloalkylcarbonylamino”, “haloalkylsulfonylamino”, “haloalkylsulfonyl-oxy”, “haloalkoxyalkyl”, “haloalkylcarbonyloxy”, “haloalkylaminoalkyl” and the like, are defined analogously to the term “haloalkyl”. Examples of “haloalkoxy” include CF3O—, CCl3CH2O—, HCF2CH2CH2— and CF3CH2—. Examples of “haloalkylthio” include CCl3S—, CF3S—, CCl3CH2S— and C1CH2CH2CH2S—. Examples of “haloalkylsulfinyl” include CF3S(O)—, CCl3S(O)—, CF3CH2S(O)— and CF3CF2S(O)—. Examples of “haloalkylsulfonyl” include CF3S(O)2—, CCl3S(O)2—, CF3CH2S(O)2— and CF3CF2S(O)2—. Examples of “haloalkenyl” include (C1)2C═CHCH2— and CF3CH2CH═CHCH2—. Examples of “haloalkenyloxy” include (C)2C═CHCH2O— and CF3CH2CH═CHCH2O—. Examples of “haloalkynyl” include HC≡CCHCl—, CF3C═C—, CCl3C═C— and FCH2C≡CCH2—. Examples of “haloalkoxyalkyl” include CF3OCH2—, C1CH2CH2OCH2CH2—, Cl3CCH2OCH2— as well as branched alkyl derivatives. Examples of “haloalkoxycarbonyl” include CF3OC(O)—, C1CH2CH2OCH2CH2—, Cl3CCH2CH2C(O)— as well as branched alkyl derivatives.


“Alkylcarbonyl” denotes a straight-chain or branched alkyl moieties bonded to a C(═O) moiety. Examples of “alkylcarbonyl” include CH3C(═O)—, CH3CH2CH2C(═O)— and (CH3)2CHC(═O)—. Examples of “alkoxycarbonyl” include CH3OC(═O)—, CH3CH2OC(═O)—, CH3CH2CH2C(═O)—, (CH3)2CHOC(═O)— and the different butoxy- or pentoxycarbonyl isomers. “Cycloalkylalkoxycarbonyl” denotes a cycloalkylalkyl moieties bonded to an oxygen atom of alkoxycarbonyl moiety. Examples of “cycloalkylalkoxycarbonyl” include cyclopropyl-CH2OC(═O)—, cyclopropyl-CH(CH3)OC(═O)— and cyclopentyl-CH2OC(═O)—.


The total number of carbon atoms in a substituent group is indicated by the “Ci-Cj” prefix where i and j are numbers from 1 to 12. For example, C1-C4 alkylsulfonyl designates methylsulfonyl through butylsulfonyl; C2 alkoxyalkyl designates CH3OCH2—; C3 alkoxyalkyl designates, for example, CH3CH(OCH3)—, CH3OCH2CH2— or CH3CH2OCH2—; and C4 alkoxyalkyl designates the various isomers of an alkyl group substituted with an alkoxy group containing a total of four carbon atoms, examples including CH3CH2CH2OCH2— and CH3CH2OCH2CH2—.


When a compound is substituted with a substituent bearing a subscript that indicates the number of said substituents can exceed 1, said substituents (when they exceed 1) are independently selected from the group of defined substituents, e.g., [R7)n], n is 1, 2, 3, 4 or 5). Further, when the subscript indicates a range, e.g. (R)i-j, then the number of substituents may be selected from the integers between i and j inclusive. When a group contains a substituent which can be hydrogen, for example R1 or R2, then when this substituent is taken as hydrogen, it is recognized that this is equivalent to said group being unsubstituted. When a variable group is shown to be optionally attached to a position, for example [R(7)n] wherein n may be 0, then hydrogen may be at the position even if not recited in the variable group definition. When one or more positions on a group are said to be “not substituted” or “unsubstituted”, then hydrogen atoms are attached to take up any free valency.


The expression “fully saturated” in relation to a ring of atoms means that the bonds between the atoms of the ring are all single. The expression “fully unsaturated” in relation to a ring means that the bonds between the atoms in the ring are single or double bonds according to valence bond theory and furthermore the bonds between the atoms in the ring include as many double bonds as possible without double bonds being cumulative (i.e. no C═C═C, N═C═C, etc.). The term “partially unsaturated” in relation to a ring denotes a ring comprising at least one ring member bonded to an adjacent ring member though a double bond and which conceptually potentially accommodates a number of non-cumulated double bonds through adjacent ring members (i.e. in its fully unsaturated counterpart form) greater than the number of double bonds present (i.e. in its partially unsaturated form). When a fully unsaturated ring satisfies Hickel's rule then it can also be described as aromatic.


Unless otherwise indicated, a “ring” or “ring system” as a component of Formula 1 (e.g., substituent Q1) is carbocyclic or heterocyclic. The term “ring system” denotes two or more fused rings. The terms “bicyclic ring system” and “fused bicyclic ring system” denote a ring system consisting of two fused rings, in which either ring can be saturated, partially unsaturated, or fully unsaturated unless otherwise indicated. The term “fused heterobicyclic ring system” denotes a fused bicyclic ring system in which at least one ring atom is not carbon. The term “ring member” refers to an atom or other moiety (e.g., C(═O), C(═S), S(O) or S(O)2) forming the backbone of a ring or ring system.


The terms “carbocyclic ring”, “carbocycle” or “carbocyclic ring system” denote a ring or ring system wherein the atoms forming the ring backbone are selected only from carbon. Unless otherwise indicated, a carbocyclic ring can be a saturated, partially unsaturated, or fully unsaturated ring. When a fully unsaturated carbocyclic ring satisfies Hickel's rule, then said ring is also called an “aromatic ring”. “Saturated carbocyclic” refers to a ring having a backbone consisting of carbon atoms linked to one another by single bonds; unless otherwise specified, the remaining carbon valences are occupied by hydrogen atoms.


The terms “heterocyclic ring”, “heterocycle” or “heterocyclic ring system” denote a ring or ring system in which at least one atom forming the ring backbone is not carbon, e.g., nitrogen, oxygen or sulfur. Typically a heterocyclic ring contains no more than 4 nitrogens, no more than 2 oxygens and no more than 2 sulfurs. Unless otherwise indicated, a heterocyclic ring can be a saturated, partially unsaturated, or fully unsaturated ring. When a fully unsaturated heterocyclic ring satisfies Hickel's rule, then said ring is also called a “heteroaromatic ring” or “aromatic heterocyclic ring”. Unless otherwise indicated, heterocyclic rings and ring systems can be attached through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen.


“Aromatic” indicates that each of the ring atoms is essentially in the same plane and has a p-orbital perpendicular to the ring plane, and that (4n+2) 1 electrons, where n is a positive integer, are associated with the ring to comply with Hickel's rule. The term “aromatic ring or ring system” denotes a carbocyclic or heterocyclic ring or ring system in which the ring or at least one ring of the ring system is aromatic. The term “aromatic ring or ring system” is also referred to as “aryl”. The term “aryl” can be used alone or in compound words such as “arylcarbonyl”. “Arylcarbonyl” denotes an aryl group bonded to a C(═O) moiety. The terms “arylalkenylalkyl” is defined similarly. The term “aromatic carbocyclic ring system” denotes a carbocyclic ring system in which at least one ring of the ring system is aromatic. The term “aromatic heterocyclic ring system” denotes a heterocyclic ring system in which at least one ring of the ring system is aromatic. The term “nonaromatic ring system” denotes a carbocyclic or heterocyclic ring system that may be fully saturated, as well as partially or fully unsaturated, provided that none of the rings in the ring system are aromatic. The term “nonaromatic carbocyclic ring system” in which no ring in the ring system is aromatic. The term “nonaromatic heterocyclic ring system” denotes a heterocyclic ring system in which no ring in the ring system is aromatic.


The term “optionally substituted” in connection with the heterocyclic rings refers to groups which are unsubstituted or have at least one non-hydrogen substituent that does not extinguish the biological activity possessed by the unsubstituted analog. As used herein, the following definitions shall apply unless otherwise indicated. The term “optionally substituted” is used interchangeably with the phrase “substituted or unsubstituted” or with the term “(un)substituted.” Unless otherwise indicated, an optionally substituted group may have a substituent at each substitutable position of the group, and each substitution is independent of the other.


When Q1 or Q2 is 5- or 6-membered nitrogen-containing heterocyclic ring, it may be attached to the remainder of Formula 1 though any available carbon or nitrogen ring atom, unless otherwise described. As noted above, Q1 and Q2 can be (among others) phenyl optionally substituted with one or more substituents selected from a group of substituents as defined in the Summary. An example of phenyl optionally substituted with one to five substituents is the ring illustrated as U-1 in Exhibit 1, wherein, for example, Rv is R7 as defined in the Summary for Q1, or Rv is R10 as defined in the Summary for Q2, and r is an integer (from 0 to 5).


As noted above, Q1 and Q2 can be (among others) a 5- or 6-membered fully unsaturated heterocyclic ring, optionally substituted with one or more substituents selected from a group of substituents as defined in the Summary. Examples of a 5- or 6-membered unsaturated aromatic heterocyclic ring optionally substituted with from one or more substituents include the rings U-2 through U-61 illustrated in Exhibit 1 wherein Rv is any substituent as defined in the Summary for Q1 and Q2, and r is an integer from 0 to 4, limited by the number of available positions on each U group. As U-29, U-30, U-36, U-37, U-38, U-39, U-40, U-41, U-42 and U-43 have only one available position, for these U groups r is limited to the integers 0 or 1, and r being 0 means that the U group is unsubstituted and a hydrogen is present at the position indicated by (Rv)r.




embedded image


embedded image


embedded image


embedded image


embedded image


embedded image


As noted above, Q1 and Q2 can be an 8- to 10-membered heterocyclic ring system optionally substituted with one or more substituents selected from a group of substituents as defined in the Summary for Q1 and Q2. Examples of 8- to 10-membered heterocyclic ring system optionally substituted with from one or more substituents include the rings U-62 through U-102 illustrated in Exhibit 2 wherein Rv is any substituent as defined in the Summary for Q1 or Q2, and r is typically an integer from 0 to 5. The free bond denoted by a straight line can be located on either ring irregardless of where they are drawn. The free bond connected to (Rv)r can be located on either ring irregardless of where they are drawn.




embedded image


embedded image


embedded image


embedded image


Although Rv groups are shown in the structures U-1 through U-102, it is noted that they do not need to be present since they are optional substituents. Note that when Rv is H when attached to an atom, this is the same as if said atom is unsubstituted. The nitrogen atoms that require substitution to fill their valence are substituted with H or R. Note that when the attachment point between (R)r and the U group is illustrated as floating, (RV)r can be attached to any available carbon atom or nitrogen atom of the U group. Note that when the attachment point on the U group is illustrated as floating, the U group can be attached to the remainder of Formula 1 through any available carbon or nitrogen of the U group by replacement of a hydrogen atom. In some embodiments, for greatest herbicidal activity, the U group is attached to the remainder of Formula 1 through an available carbon or nitrogen on a fully unsaturated ring of the U group. Note that some U groups can only be substituted with less than 4 Rv groups (e.g., U-2 through U-5, U-7 through U-48, and U-52 through U-61).


As noted above, R6 and Q2 can be taken together with the nitrogen atom to which they are both bonded to form an 8- to 10-membered bicyclic ring system. Examples of R6 and Q2 taken together are shown in Exhibit 3.




embedded image


In the present disclosure, the term “pyrrolidinone” and related terms such as “pyrrolidinone ring” refer to 2-oxo-pyrrolidine derivatives according to the Chemical Abstracts system of nomenclature, including derivatives in which the oxygen atom of the 2-oxo moiety is replaced by S or NR12 as Y1, unless limited to oxygen by particular context.


A wide variety of synthetic methods are known in the art to enable preparation of aromatic and nonaromatic heterocyclic rings and ring systems; for extensive reviews see the eight volume set of Comprehensive Heterocyclic Chemistry, A. R. Katritzky and C. W. Rees editors-in-chief, Pergamon Press, Oxford, 1984 and the twelve volume set of Comprehensive Heterocyclic Chemistry H, A. R. Katritzky, C. W. Rees and E. F. V. Scriven editors-in-chief, Pergamon Press, Oxford, 1996.


Compounds of this disclosure can exist as one or more stereoisomers. The various stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers. Stereoisomers are isomers of identical constitution but differing in the arrangement of their atoms in space and include enantiomers, diastereomers, cis-trans isomers (also known as geometric isomers) and atropisomers. Atropisomers result from restricted rotation about single bonds where the rotational barrier is high enough to permit isolation of the isomeric species. One skilled in the art will appreciate that one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other stereoisomer(s) or when separated from the other stereoisomer(s). Additionally, the skilled artisan knows how to separate, enrich, and/or to selectively prepare said stereoisomers. Compounds of this disclosure may be present as a mixture of stereoisomers, individual stereoisomers or as an optically active form. Particularly when R4 and R5 are each H, the C(O)N(Q2)(R6) and Q1 substituents are typically mostly in the thermodynamically preferred trans configuration on the pyrrolidinone ring.


For example, as shown in the following, the C(O)N(Q2)(R6) moiety (i.e. in Formula 1 wherein both Y1 and Y2 are O; and J is —CR2R3— and R2 and R3 are both H) bonded to the carbon at the 3-position of the cyclic amide ring and Q1 bonded to the carbon at the 4-position of the cyclic amide ring are generally found in the trans configuration. These two carbon atoms both possess a chiral center. The most prevalant pair of enantiomers are depicted as Formula 1′ and Formula 1″. While this disclosure pertains to all stereoisomers, in some embodiments, the enantiomer for biological operability is identified as Formula 1′. For a comprehensive discussion of all aspects of stereoisomerism, see Ernest L. Eliel and Samuel H. Wilen, Stereochemistry of Organic Compounds, John Wiley & Sons, 1994.




embedded image


The skilled artisan will also recognize that the carbon atom at the 5-position of the pyrrolidinone ring (i.e. when J is —CR2R3—, the carbon atom to which both R2 and R3 are bonded) also contains a stereocenter indicated by a (*) as shown in Formula 1′″. This disclosure pertains to all stereoisomers, and therefore, when either R2 or R3 are other than the same substituent, then a mixture of diastereomers is possible.




embedded image


Molecular depictions drawn herein follow standard conventions for depicting stereochemistry. To indicate stereoconfiguration, bonds rising from the plane of the drawing and towards the viewer are denoted by solid wedges wherein the broad end of the wedge is attached to the atom rising from the plane of the drawing towards the viewer. Bonds going below the plane of the drawing and away from the viewer are denoted by dashed wedges wherein the narrow end of the wedge is attached to the atom further away from the viewer. Constant width lines indicate bonds with a direction opposite or neutral relative to bonds shown with solid or dashed wedges; constant width lines also depict bonds in molecules or parts of molecules in which no particular stereoconfiguration is intended to be specified. This disclosure also comprises racemic mixtures, for example, equal amounts of the enantiomers of Formulae 1′ and 1″ (and optionally 1′″). In addition, this disclosure includes compounds that are enriched compared to the racemic mixture in an enantiomer of Formula 1. Also included are the essentially pure enantiomers of compounds of Formula 1, for example, Formula 1′ and Formula 1″.


When enantiomerically enriched, one enantiomer is present in greater amounts than the other, and the extent of enrichment can be defined by an expression of enentiomeric ratio (ER) expressed as the relative area % of the two entantiomers determined by chiral high-performance liquid chromatography.


In some embodiments, the compositions of this disclosure have at least a 50% ER. In some embodiments, the compositions of this disclosure have at least a 75% ER. In some embodiments, the compositions of this disclosure have at least a 90% ER. In some embodiments, the compositions of this disclosure have at least a 94% ER of the more active isomer. Of particular note are enantiomerically pure embodiments of the more active isomer.


Compounds of Formula 1 can comprise additional chiral centers. For example, substituents and other molecular constituents such as R2, R3 and R6 may themselves contain chiral centers. This disclosure comprises racemic mixtures as well as enriched and essentially pure stereoconfigurations at these additional chiral centers.


Compounds of this disclosure can exist as one or more conformational isomers due to restricted rotation about the amide bond C(O)N(Q2)(R6) in Formula 1. This disclosure comprises mixtures of conformational isomers. In addition, this disclosure includes compounds that are enriched in one conformer relative to others. Compounds of Formula 1 typically exist in more than one form, and Formula 1 thus include all crystalline and non-crystalline forms of the compounds they represent. Non-crystalline forms include embodiments which are solids such as waxes and gums as well as embodiments which are liquids such as solutions and melts. Crystalline forms include embodiments which represent essentially a single crystal type and embodiments which represent a mixture of polymorphs (i.e. different crystalline types). The term “polymorph” refers to a particular crystalline form of a chemical compound that can crystallize in different crystalline forms, these forms having different arrangements and/or conformations of the molecules in the crystal lattice. Although polymorphs can have the same chemical composition, they can also differ in composition due the presence or absence of co-crystallized water or other molecules, which can be weakly or strongly bound in the lattice. Polymorphs can differ in such chemical, physical and biological properties as crystal shape, density, hardness, color, chemical stability, melting point, hygroscopicity, suspensibility, dissolution rate and biological availability. One skilled in the art will appreciate that a polymorph of a compound of Formula 1 can exhibit beneficial effects (e.g., suitability for preparation of useful formulations, improved biological performance) relative to another polymorph or a mixture of polymorphs of the same compound of Formula 1. Preparation and isolation of a particular polymorph of a compound of Formula 1 can be achieved by methods known to those skilled in the art including, for example, crystallization using selected solvents and temperatures. For a comprehensive discussion of polymorphism see R. Hilfiker, Ed., Polymorphism in the Pharmaceutical Industry, Wiley-VCH, Weinheim, 2006.


One skilled in the art will appreciate that not all nitrogen-containing heterocycles can form N-oxides since the nitrogen requires an available lone pair for oxidation to the oxide; one skilled in the art will recognize those nitrogen-containing heterocycles which can form N-oxides. One skilled in the art will also recognize that tertiary amines can form N-oxides. Synthetic methods for the preparation of N-oxides of heterocycles and tertiary amines are very well known by one skilled in the art including the oxidation of heterocycles and tertiary amines with peroxy acids such as peracetic and m-chloroperbenzoic acid (MCPBA), hydrogen peroxide, alkyl hydroperoxides such as t-butyl hydroperoxide, sodium perborate, and dioxiranes such as dimethyldioxirane. These methods for the preparation of N-oxides have been extensively described and reviewed in the literature, see for example: T. L. Gilchrist in Comprehensive Organic Synthesis, vol. 7, pp 748-750, S. V. Ley, Ed., Pergamon Press; M. Tisler and B. Stanovnik in Comprehensive Heterocyclic Chemistry, vol. 3, pp 18-20, A. J. Boulton and A. McKillop, Eds., Pergamon Press; M. R. Grimmett and B. R. T. Keene in Advances in Heterocyclic Chemistry, vol. 43, pp 149-161, A. R. Katritzky, Ed., Academic Press; M. Tisler and B. Stanovnik in Advances in Heterocyclic Chemistry, vol. 9, pp 285-291, A. R. Katritzky and A. J. Boulton, Eds., Academic Press; and G. W. H. Cheeseman and E. S. G. Werstiuk in Advances in Heterocyclic Chemistry, vol. 22, pp 390-392, A. R. Katritzky and A. J. Boulton, Eds., Academic Press.


One skilled in the art recognizes that because in the environment and under physiological conditions salts of chemical compounds are in equilibrium with their corresponding nonsalt forms, salts share the biological utility of the nonsalt forms. Thus a wide variety of salts of a compound of Formula 1 are useful for control of undesired vegetation (i.e. are agriculturally suitable). The salts of a compound of Formula 1 include acid-addition salts with inorganic or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic or valeric acids. When a compound of Formula 1 contains an acidic moiety such as a carboxylic acid or phenol, salts also include those formed with organic or inorganic bases such as pyridine, triethylamine or ammonia, or amides, hydrides, hydroxides or carbonates of sodium, potassium, lithium, calcium, magnesium or barium. Accordingly, the present disclosure comprises compounds selected from Formula 1, N-oxides and agriculturally suitable salts thereof.


Embodiments of the present disclosure as described in the Summary include (where Formula 1 as used in the following Embodiments includes N-oxides and salts thereof):


Embodiment 1





    • A compound of Formula 1 wherein Q1 is a 4- or 7-membered heterocyclic ring or an 8- to 10-membered bicyclic ring system, each ring or ring system containing ring members selected from carbon atoms and 1 to 5 heteroatoms independently selected from up to 2 O, up to 2 S and up to 5 N atoms, wherein up to 3 carbon ring members are independently selected from C(═O) and C(═S), and the sulfur atom ring members are independently selected from S(═O)u(═NR8)v, each ring or ring system optionally substituted with up to 5 substituents independently selected from R7 on carbon atom ring members and selected from R9 on nitrogen atom ring members.





Embodiment 2





    • A compound of Embodiment 1 wherein Q1 is C2-C10 alkenyl, C2-C10 alkynyl, C2-C10 haloalkenyl, C2-C10 haloalkynyl, C4-C10 cycloalkenyl, C4-C10 halocycloalkenyl, C2-C8 alkylcarbonyl or C2-C8 alkoxyalkyl.





Embodiment 3





    • A compound of Embodiment 1 wherein Q1 is an 8- to 10-membered bicyclic ring system, containing ring members selected from carbon atoms and 1 to 5 heteroatoms independently selected from up to 2 O, up to 2 S and up to 5 N atoms, wherein up to 3 carbon ring members are independently selected from C(═O) and C(═S), and the sulfur atom ring members are independently selected from S(═O)u(═NR8)v, the said ring system optionally substituted with up to 5 substituents independently selected from R7 on carbon atom ring members and selected from R9 on nitrogen atom ring members.





Embodiment 4





    • A compound of Embodiment 1 wherein Q1 is a 4- or 7-membered heterocyclic ring, containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 4 N atoms, wherein up to 3 carbon ring members are independently selected from C(═O) and C(═S), and the sulfur atom ring members are independently selected from S(═O)u(═NR8)v, the said ring optionally substituted with up to 5 substituents independently selected from R7 on carbon atom ring members and selected from R9 on nitrogen atom ring members.





Embodiment 5





    • A compound of Formula 1 wherein Q1 is a phenyl ring optionally substituted with up to 5 substituents independently selected from R7.





Embodiment 6





    • A compound of Embodiment 5 wherein Q1 is a phenyl ring substituted with 1 to 3 substituents independently selected from R7.





Embodiment 7





    • A compound of Embodiment 6 wherein Q1 is a phenyl ring substituted with 1 to 2 substituents independently selected from R7.





Embodiment 8





    • A compound of Formula 1 or any one of Embodiments 5 through 7 wherein Q1 is a phenyl ring having at least one substituent selected from R7 at the para position and optionally other substituents.





Embodiment 9





    • A compound of Formula 1 or any one of Embodiments 5 through 8 wherein Q1 is a phenyl ring substituted with at least two substituents selected from R7, and one substituent is at the para position and at least one other substituent is at a meta position of the phenyl ring.





Embodiment 10





    • A compound of Formula 1 wherein Q2 is a 4- or 7-membered heterocyclic ring or an 8- to 10-membered bicyclic ring system, each ring or ring system containing ring members selected from carbon atoms and 1 to 5 heteroatoms independently selected from up to 2 O, up to 2 S and up to 5 N atoms, wherein up to 3 carbon ring members are independently selected from C(═O) and C(═S), and the sulfur atom ring members are independently selected from S(═O)u(═NR8)v, each ring or ring system optionally substituted with up to 5 substituents independently selected from R7 on carbon atom ring members and selected from R9 on nitrogen atom ring members.





Embodiment 11





    • A compound of Formula 1 wherein Q2 is C2-C10 alkenyl, C2-C10 alkynyl, C2-C10 haloalkenyl, C2-C10 haloalkynyl, C4-C10 cycloalkenyl, C4-C10 halocycloalkenyl, C2-C8 alkylcarbonyl or C2-C8 alkoxyalkyl.





Embodiment 12





    • A compound of Embodiment 10 wherein Q2 is an 8- to 10-membered bicyclic ring system, containing ring members selected from carbon atoms and 1 to 5 heteroatoms independently selected from up to 2 O, up to 2 S and up to 5 N atoms, wherein up to 3 carbon ring members are independently selected from C(═O) and C(═S), and the sulfur atom ring members are independently selected from S(═O)u(═NR8)v, the said ring system optionally substituted with up to 5 substituents independently selected from R10 on carbon atom ring members and selected from R11 on nitrogen atom ring members.





Embodiment 13





    • A compound of Embodiment 10 wherein Q2 is a 4- or 7-membered heterocyclic ring, containing ring members selected from carbon atoms and 1 to 5 heteroatoms independently selected from up to 2 O, up to 2 S and up to 5 N atoms, wherein up to 3 carbon ring members are independently selected from C(═O) and C(═S), and the sulfur atom ring members are independently selected from S(═O)u(═NR8)v, the said ring optionally substituted with up to 5 substituents independently selected from R10 on carbon atom ring members and selected from R11 on nitrogen atom ring members.





Embodiment 14





    • A compound of Formula 1 wherein Q2 is a phenyl ring substituted with up to 5 substituents independently selected from R10.





Embodiment 15





    • A compound of Embodiment 14 wherein Q2 is a phenyl ring substituted with 1 to 3 substituents independently selected from R10.





Embodiment 16





    • A compound of Embodiment 15 wherein Q2 is a phenyl ring substituted with 1 to 2 substituents independently selected from R10.





Embodiment 17





    • A compound of Formula 1 or any one of Embodiments 1 through 16 wherein Q2 is a phenyl ring having at least one substituent selected from R10 at an ortho position and optionally other substituents.





Embodiment 18





    • A compound of Formula 1 or any one of Embodiments 1 through 17 wherein Q2 is a phenyl ring substituted with at least two substituents selected from R10, and at least one substituent is at an ortho position and at least one substituent is at an adjacent meta position of the phenyl ring.





Embodiment 19





    • A compound of Formula 1 or any one of Embodiments 1 through 17 wherein when Q2 is a phenyl ring substituted with at least two substituents selected from R10, then at least one substituent is at an ortho position and at least one substituent is at para position of the phenyl ring.





Embodiment 20





    • A compound of Formula 1 wherein J is —CR2R3—, —NR2a— or —O—.





Embodiment 21





    • A compound of Embodiment 20 wherein J is —CR2R3—.





Embodiment 22





    • A compound of Embodiment 20 wherein J is —NR2a—.





Embodiment 23





    • A compound of Embodiment 20 wherein J is —O—.





Embodiment 24





    • A compound of Formula 1 or Embodiment 22 wherein R2a is C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl or C1-C6 alkoxy.





Embodiment 25





    • A compound of Formula 1 or any one of Embodiments 1 through 24 wherein, independently, each R7 and R10 is independently halogen, hydroxy, cyano, nitro, amino, C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C2-C4 haloalkynyl, C2-C6 alkoxyalkyl, C3-C6 alkoxyalkoxyalkyl, C2-C6 haloalkoxyalkyl, C2-C6 haloalkoxyhaloalkoxy, C3-C6 cycloalkyl, cyclopropylmethyl, 1-methylcyclopropyl, 2-methylcyclopropyl, C1-C4 nitroalkyl, C2-C4 nitroalkenyl, C2-C4 alkoxyalkyl, C2-C4 haloalkoxyalkyl, C3-C4 cycloalkyl, C3-C4 halocycloalkyl, cyclopropylmethyl, methylcyclopropyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkenyloxy, C2-C4 haloalkenyloxy, C3-C4 alkynyloxy, C3-C4 haloalkynyloxy, C3-C4 cycloalkoxy, C1-C4 alkylthio, C1-C4 haloalkylthio, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylsulfonyl, hydroxy, formyl, C2-C4 alkylcarbonyl, C2-C4 alkylcarbonyloxy, C1-C4 alkylsulfonyloxy, C1-C4 haloalkylsulfonyloxy, amino, C1-C4 alkylamino, C2-C4 dialkylamino, formylamino, C2-C4 alkylcarbonylamino, —SF5, —SCN, C3-C4 trialkylsilyl, trimethylsilylmethyl or trimethylsilylmethoxy.





Embodiment 26





    • A compound of Formula 1 wherein each R7 and R10 is independently hydroxy, amino, C2-C8 alkoxyalkyl, C3-C8 alkoxyalkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 haloalkoxyhaloalkoxy, C3-C6 cycloalkyl, cyclopropylmethyl, 1-methylcyclopropyl, 2-methylcyclopropyl, C2-C8 alkylamino, C2-C8 dialkylamino, C2-C8 halodialkylamino or C3-C8 cycloalkylamino; or G2; or
      • each R7 is independently R26S(═O)═N—, R26S(═O)2NR25—C(═O)—, R26(R25N═)qS(═O)p—, wherein the free bond projecting to the right indicates the connecting point to Q1; or
      • each R10 is independently R17ON=CR17a—, (R18)2C═NO—, (R19)2NN═CR17a—, (R18)2C═NNR20a—, R20N=CR17a—, (R18)2C═N—, R17ON=CR17aC(R23b)2—, (R18)2C═NOC(R24a)2—, R26S(═O)═N—, R26S(═O)2NR25—C(═O)— or R26(R25N═)qS(═O)p—, wherein the free bond projecting to the right indicates the connecting point to Q2;





Embodiment 27





    • A compound of Embodiment 26 wherein each p and q are independently 0, 1 or 2 in each instance of R26(R25N═)qS(═O)p—, provided that the sum of u and v is 0, 1 or 2 and when p is 0, q is other than 1 or 2;





Embodiment 28





    • A compound of Embodiment 26 wherein
      • each R17 is independently H, C1-C6 alkyl, C3-C8 cycloalkyl, C4-C8 cycloalkylalkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C10 cycloalkylcarbonyl, C2-C8 alkoxycarbonyl, C2-C8 haloalkoxycarbonyl, C4-C10 cycloalkoxycarbonyl, C2-C8 alkylaminocarbonyl, C3-C10 dialkylaminocarbonyl, C4-C10 cycloalkylaminocarbonyl, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C3-C8 cycloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C1-C6 alkylaminosulfonyl, C2-C8 dialkylaminosulfonyl, C3-C10 trialkylsilyl or G1;
      • each R17a is independently H, C1-C6 alkyl, C3-C8 cycloalkyl, C4-C8 cycloalkylalkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3-C8 cycloalkylthio, C3-C10 trialkylsilyl or G1;
      • each R18 is independently H, hydroxy, C1-C6 alkyl, C3-C8 cycloalkyl, C4-C8 cycloalkylalkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C10 cycloalkylcarbonyl, C2-C8 alkoxycarbonyl, C2-C8 haloalkoxycarbonyl, C4-C10 cycloalkoxycarbonyl, C2-C8 alkylaminocarbonyl, C3-C10 dialkylaminocarbonyl, C4-C10 cycloalkylaminocarbonyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3-C8 cycloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C3-C8 cycloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C1-C6 alkylaminosulfonyl, C2-C8 dialkylaminosulfonyl, C3-C10 trialkylsilyl or G1;
      • each R19 is independently H, C1-C6 alkyl, C3-C8 cycloalkyl, C4-C8 cycloalkylalkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C10 cycloalkylcarbonyl, C2-C8 alkoxycarbonyl, C2-C8 haloalkoxycarbonyl, C4-C10 cycloalkoxycarbonyl, C2-C8 alkylaminocarbonyl, C3-C10 dialkylaminocarbonyl, C4-C10 cycloalkylaminocarbonyl, C1-C6 alkoxy, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C3-C8 cycloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C1-C6 alkylaminosulfonyl, C2-C8 dialkylaminosulfonyl, C3-C10 trialkylsilyl or G1;
      • each R20 is independently H, hydroxy, amino, C1-C6 alkyl, C3-C8 cycloalkyl, C4-C8 cycloalkylalkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C10 cycloalkylcarbonyl, C2-C8 alkoxycarbonyl, C2-C8 haloalkoxycarbonyl, C4-C10 cycloalkoxycarbonyl, C2-C8 alkylaminocarbonyl, C3-C10 dialkylaminocarbonyl, C4-C10 cycloalkylaminocarbonyl, C1-C6 alkoxy, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C3-C8 cycloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C1-C6 alkylaminosulfonyl, C2-C8 dialkylaminosulfonyl, C3-C10 trialkylsilyl or G1;
      • each R20a is independently H, C1-C6 alkyl, C3-C8 cycloalkyl, C4-C8 cycloalkylalkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C1-C6 alkoxy, C3-C10 trialkylsilyl or G1;
      • each R23b is independently H, halogen, cyano, hydroxy, C1-C4 alkyl, C3-C8 cycloalkyl, C4-C8 cycloalkylalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkoxyalkyl, C2-C4 alkylcarbonyl, C2-C4 alkoxycarbonyl or C3-C6 cycloalkyl;
      • each R24a is independently H, C1-C4 alkyl, C3-C8 cycloalkyl, C4-C8 cycloalkylalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkoxyalkyl, C2-C4 alkylcarbonyl, C2-C4 alkoxycarbonyl or C3-C6 cycloalkyl;
      • each R25 is independently H, cyano, C2-C3 alkylcarbonyl or C2-C3 haloalkylcarbonyl;
      • each R26 is independently H, C1-C6 alkyl, C3-C8 cycloalkyl, C4-C8 cycloalkylalkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C1-C6 alkoxy, C3-C10 trialkylsilyl or G1; and





Embodiment 29





    • A compound of Formula 1 or Embodiment 26 wherein each G2 is a 5- or 6-membered heterocyclic ring, each optionally substituted on ring members with up to 5 substituents independently selected from R14;





Embodiment 30





    • A compound of Embodiment 25 wherein each R7 is independently halogen, cyano, C1-C2 alkyl, C1-C3 haloalkyl or C1-C3 alkylsulfonyl.





Embodiment 31





    • A compound of Embodiment 30 wherein each R7 is independently halogen or C1-C2 haloalkyl.





Embodiment 32





    • A compound of Embodiment 31 wherein each R7 is independently halogen or C1 haloalkyl.





Embodiment 33





    • A compound of Embodiment 32 wherein each R7 is independently halogen or C1 fluoroalkyl.





Embodiment 34





    • A compound of Embodiment 33 wherein each R7 is independently halogen or CF3.





Embodiment 35





    • A compound of Embodiment 34 wherein each R7 is independently F, C1, Br or CF3.





Embodiment 36





    • A compound of Embodiment 35 wherein each R7 is independently F or CF3.





Embodiment 37





    • A compound of Embodiment 35 or 36 wherein at most only one CF3 substituent is present and is at the para position of the Q1 phenyl ring.





Embodiment 38





    • A compound of Embodiment 25 or Embodiment 26 wherein each R10 is independently halogen, cyano, nitro, C1-C2 alkyl, C1-C3 haloalkyl or C1-C3 alkylsulfonyl.





Embodiment 39





    • A compound of Embodiment 38 wherein each R10 is independently halogen or C1-C2 haloalkyl.





Embodiment 40





    • A compound of Embodiment 39 wherein each R10 is independently halogen or C1 haloalkyl.





Embodiment 41





    • A compound of Embodiment 40 wherein each R10 is independently halogen or C1 fluoroalkyl.





Embodiment 42





    • A compound of Embodiment 41 wherein each R10 is independently halogen or CF3.





Embodiment 43





    • A compound of Embodiment 42 wherein each R10 is independently F, C1, Br or CF3.





Embodiment 44





    • A compound of Embodiment 43 wherein each R10 is independently F or CF3.





Embodiment 45





    • A compound of Embodiment 44 wherein each R10 is F.





Embodiment 46





    • A compound of Formula 1 or any one of Embodiments 1 through 45 wherein each R9 and R11 is independently H or C1-C2 alkyl.





Embodiment 47





    • A compound of Embodiment 46 wherein, independently, each R9 and R11 is CH3.





Embodiment 48





    • A compound of Formula 1 wherein Y1 and Y2 are each independently NR12;





Embodiment 49





    • A compound of Embodiment 48 wherein each R12 is independently hydroxy, CHO, C2-C6 alkylcarbonyl or C2-C6 haloalkylcarbonyl.





Embodiment 50





    • A compound of Formula 1 or any one of Embodiments 1 through 47 wherein Y1 is O.





Embodiment 51





    • A compound of Formula 1 or any one of Embodiments 1 through 50 wherein Y2 is O.





Embodiment 52





    • A compound of Formula 1 or any one of Embodiments 1 through 51 wherein Y1 and Y2 are both 0.





Embodiment 53





    • A compound of Formula 1 wherein R1 is cyano, formyl, C3-C8 alkylcarbonylalkyl, —C(C1-C4 alkyl)=N—O(C1-C4 alkyl), —C(O)NH2, C2-C6 cyanoalkyl, C3-C6 cycloalkyl, C4-C8 cycloalkenyl; or arylcarbonyl, arylalkenylalkyl, arylcarbonylalkyl or —CPh=N—O(C1-C4 alkyl), each optionally substituted on ring members with up to 5 substituents independently selected from R13; or G1; or W1G1.





Embodiment 54





    • A compound of Embodiment 53 wherein R1 is cyano, formyl, C3-C8 alkylcarbonylalkyl, —C(C1-C4 alkyl)=N—O(C1-C4 alkyl), —C(O)NH2, C2-C6 cyanoalkyl, C3-C6 cycloalkyl, C4-C8 cycloalkenyl; or arylcarbonyl, arylalkenylalkyl, arylcarbonylalkyl or —CPh=N—O(C1-C4 alkyl), each optionally substituted on ring members with up to 5 substituents independently selected from R13.





Embodiment 55





    • A compound of Embodiment 53 wherein R1 is W1G1.





Embodiment 56





    • A compound of Embodiment 55 wherein each G1 is independently phenyl, or a 5- or 6-membered heterocyclic ring, each optionally substituted on ring members with up to 5 substituents independently selected from R13.





Embodiment 57





    • A compound of Embodiment 56 wherein W1 is C1-C3 alkylene, C2-C4 alkenylene, C2-C4 alkynylene, —(C1-C2 alkylene)C(═O)—, —C(═O)(C1-C2 alkylene)-, —CH2—, —CH2NH—, —OCH2—, —NCH2—, —N—, —O—, —S—, —SO— or —SO2— wherein the free bond projecting to the left indicates the connecting point of W1 to N and the free bond projecting to the right indicates the connecting point of W1 to G1.





Embodiment 58





    • A compound of Formula 1 or any one of Embodiments 1 through 52 wherein R1 is H, C1-C6 alkyl, C1-C6 haloalkyl, C2-C8 alkylcarbonyl or C4-C8 cycloalkylalkyl.





Embodiment 59





    • A compound of Embodiment 58 wherein R1 is H, C1-C6 alkyl or C1-C6 haloalkyl.





Embodiment 60





    • A compound of Embodiment 59 wherein R1 is H, Me, Et or CHF2.





Embodiment 61





    • A compound of Embodiment 60 wherein R1 is H, Me or Et.





Embodiment 62





    • A compound of Embodiment 61 wherein R1 is H or CH3.





Embodiment 63





    • A compound of Embodiment 62 wherein R1 is CH3.





Embodiment 64





    • A compound of Embodiment 62 wherein R1 is H.





Embodiment 65





    • A compound of Formula 1 wherein R1 and R2a are taken together as C3-C6 alkylene or —CH2OCH2—.





Embodiment 66





    • A compound of Formula 1 wherein R2 and R3 are each independently hydroxy, C1-C4 haloalkyl or C1-C4 alkoxy.





Embodiment 67





    • A compound of Formula 1 or any one of Embodiments 1 through 20 or Embodiments 24 through 66 wherein R2 is H or CH3.





Embodiment 68





    • A compound of Embodiment 67 wherein R2 is H.





Embodiment 69





    • A compound of Formula 1 or any one of Embodiments 1 through 20 or Embodiments 24 through 68 wherein R3 is H or CH3.





Embodiment 70





    • A compound of Embodiment 69 wherein R3 is H.





Embodiment 71





    • A compound of Formula 1 wherein R2 and R3 are taken together with the carbon atom to which they are bonded to form a C3-C7 cycloalkyl ring.





Embodiment 72





    • A compound of Formula 1 wherein R4 and R5 are each independently hydroxy, C1-C4 alkoxy or C1-C4 haloalkyl.





Embodiment 73





    • A compound of Formula 1 or any one of Embodiments 1 through 71 wherein R4 is H or CH3.





Embodiment 74





    • A compound of Embodiment 73 wherein R4 is H.





Embodiment 75





    • A compound of Formula 1 or any one of Embodiments 1 through 74 wherein R5 is H or CH3.





Embodiment 76





    • A compound of Embodiment 75 wherein R5 is H.





Embodiment 77





    • A compound of Formula 1 or any one of Embodiments 1 through 76 wherein R6 is H or CH3.





Embodiment 78





    • A compound of Embodiment 77 wherein R6 is H.





Embodiment 79





    • A compound of Formula 1 wherein R6 and Q2 are taken together with the nitrogen atom to which they are bonded to form an 8- to 10-membered bicyclic ring system, each ring or ring system containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 4 N atoms, wherein up to 3 carbon ring members are independently selected from C(═O) and C(═S), and the sulfur atom ring members are independently selected from S(═O)u(═NR8)v, each ring or ring system optionally substituted with up to 5 substituents independently selected from R7 on carbon atom ring members and selected from R9 on nitrogen atom ring members.





Embodiment 80





    • A compound of Formula 1 or any one of Embodiments 1 through 78 wherein Q2 is other than 1H-indazol-5-yl optionally substituted at the 3-position.





Embodiment 81





    • A compound of Embodiment 80 wherein Q2 is other than 1H-indazol-5-yl optionally substituted at the 1- and 3-positions.





Embodiment 82





    • A compound of Embodiment 81 wherein Q2 is other than optionally substituted 1H-indazol-5-yl.





Embodiment 83





    • A compound of any one of Embodiments 1 through 82 wherein Q1 is other than unsubstituted phenyl.





Embodiment 84





    • A compound of any one of Embodiments 1 through 83 wherein Q2 is other than unsubstituted pyridinyl.





Embodiment 85





    • A compound of any one of Embodiments 1 through 84 wherein Q1 is other than optionally substituted naphthalenyl.





Embodiment 86





    • A compound of any one of Embodiments 1 through 85 wherein G2 is other than optionally substituted phenyl.





Embodiment 87





    • A compound of any one of Embodiments 1 through 85 wherein G2 is other then optionally substituted phenyl at the 4 position (of Q).





Embodiment 88





    • A compound of any one of Embodiments 1 through 85 wherein G2 is other than optionally substituted phenoxy





Embodiment 89





    • A compound of any one of Embodiments 1 through 85 wherein G2 is other than optionally substituted phenoxy at the 4-position (of Q).





Embodiment 90





    • A compound of Formula 1 or any one of Embodiments 1 through 89 wherein the stereochemistry at 4-position is S.





Embodiment 91





    • A compound of Formula 1 wherein when R1 is H, the C(Y2)N(Q2)(R6) moiety bonded to the carbon at the 3-position and the Q1 moiety bonded to the carbon at the 4-position of the cyclic amide ring are in the trans configuration.





Embodiment 92





    • A compound of Formula 1 wherein Q1 is an 8- to 10-membered carbocyclic bicyclic ring system, wherein the ring system is optionally substituted with up to 5 substituents independently selected from R7.





Embodiment 93





    • A compound of Formula 1 wherein Q1 is an 8- to 10-membered heterobicyclic ring system, each ring or ring system containing ring members selected from carbon atoms and 1 to 5 heteroatoms independently selected from up to 2 O, up to 2 S and up to 5 N atoms, wherein up to 3 carbon ring members are independently selected from C(═O) and C(═S), and the sulfur atom ring members are independently selected from S(═O)u(═NR8)v, and the ring system is optionally substituted with up to 5 substituents independently selected from R7 on carbon atom ring members and selected from R9 on nitrogen atom ring members.





Embodiment 94





    • A compound of Formula 1 wherein each of R7 and R10 is independently halogen, hydroxy, cyano, nitro, amino, C1-C8 alkyl, C1-C8 cyanoalkyl, C1-C8 cyanoalkoxy, C1-C8 haloalkyl, C1-C8 nitroalkyl, C2-C8 alkenyl, C2-C8 haloalkenyl, C2-C8 nitroalkenyl, C2-C8 alkynyl, C2-C8 haloalkynyl, C2-C8 alkoxyalkyl, C3-C8 alkoxyalkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 haloalkoxyhaloalkoxy, C3-C6 cycloalkyl, cyclopropylmethyl, 1-methylcyclopropyl, 2-methylcyclopropyl, C4-C10 cycloalkylalkyl, C4-C10 halocycloalkylalkyl, C5-C12 alkylcycloalkylalkyl, C5-C12 cycloalkylalkenyl, C5-C12 cycloalkylalkynyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C4-C10 alkylcycloalkyl, C6-C12 cycloalkylcycloalkyl, C3-C8 cycloalkenyl, C3-C8 halocycloalkenyl, C2-C8 haloalkoxyalkoxy, C2-C8 alkoxyalkoxy, C4-C10 cycloalkoxyalkyl, C3-C10 alkoxyalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylamino, C2-C8 dialkylamino, C2-C8 halodialkylamino, C2-C8 alkylaminoalkyl, C2-C8 haloalkylaminoalkyl, C4-C10 cycloalkylaminoalkyl, C3-C10 dialkylaminoalkyl, —CHO, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C10 cycloalkylcarbonyl, —C(═O)OH, C2-C8 alkoxycarbonyl, C2-C8 haloalkoxycarbonyl, C4-C10 cycloalkoxycarbonyl, C5-C12 cycloalkylalkoxycarbonyl, —C(═O)NH2, C2-C8 alkylaminocarbonyl, C4-C10 cycloalkylaminocarbonyl, C3-C10 dialkylaminocarbonyl, C1-C8 alkoxy, C1-C8 haloalkoxy, C2-C8 alkoxyalkoxy, C2-C8 alkenyloxy, C2-C8 haloalkenyloxy, C3-C8 alkynyloxy, C3-C8 haloalkynyloxy, C3-C8 cycloalkoxy, C3-C8 halocycloalkoxy, C4-C10 cycloalkylalkoxy, C3-C10 alkylcarbonylalkoxy, C2-C8 alkylcarbonyloxy, C2-C8 haloalkylcarbonyloxy, C4-C10 cycloalkylcarbonyloxy, C1-C8 alkylsulfonyloxy, C1-C8 haloalkylsulfonyloxy, C1-C8 alkylthio, C1-C8 haloalkylthio, C3-C8 cycloalkylthio, C1-C8 alkylsulfinyl, C1-C8 haloalkylsulfinyl, C1-C8 alkylsulfonyl, C1-C8 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, formylamino, C2-C8 alkylcarbonylamino, C2-C8 haloalkylcarbonylamino, C3-C8 cycloalkylamino, C2-C8 alkoxycarbonylamino, C1-C6 alkylsulfonylamino, C1-C6 haloalkylsulfonylamino, —SF5, —SCN, SO2NH2, C3-C12 trialkylsilyl, C4-C12 trialkylsilylalkyl or C4-C12 trialkylsilylalkoxy; or G2.





Embodiment 95





    • A compound of Formula 1 wherein each of R9 and R11 is independently cyano, C1-C3 alkyl, C2-C3 alkenyl, C2-C3 alkynyl, C3-C6 cycloalkyl, C2-C3 alkoxyalkyl, C1-C3 alkoxy, C2-C3 alkylcarbonyl, C2-C3 alkoxycarbonyl, C2-C3 alkylaminoalkyl or C3-C4 dialkylaminoalkyl





Embodiment 96





    • A compound of Formula 1 wherein at least one of R7 is C1-C8 hydroxyalkyl.





Embodiment 97





    • A compound of Formula 1 wherein at least one of R9 is C1-C8 hydroxyalkyl.





Embodiment 98





    • A compound of Formula 1 wherein at least one of R10 is C1-C8 hydroxyalkyl.





Embodiment 99





    • A compound of Formula 1 wherein at least one of R11 is C1-C8 hydroxyalkyl.





Embodiments of this disclosure, including Embodiments 1-99 above as well as any other embodiments described herein, can be combined in any manner, and the descriptions of variables in the embodiments pertain not only to the compounds of Formula 1 but also to the starting compounds and intermediate compounds useful for preparing the compounds of Formula 1. In addition, embodiments of this disclosure, including Embodiments 1-91 above as well as any other embodiments described herein, and any combination thereof, pertain to the compositions and methods of the present disclosure.


Embodiment T1





    • A compound of Formula 1 wherein Q1 is a 4- or 7-membered heterocyclic ring or an 8- to 10-membered bicyclic ring system, each ring or ring system containing ring members selected from carbon atoms and 1 to 5 heteroatoms independently selected from up to 2 O, up to 2 S and up to 5 N atoms, wherein up to 3 carbon ring members are independently selected from C(═O) and C(═S), and the sulfur atom ring members are independently selected from S(═O)u(═NR8)v, each ring or ring system optionally substituted with up to 5 substituents independently selected from R7 on carbon atom ring members and selected from R9 on nitrogen atom ring members.





Embodiment T2





    • A compound of Formula 1 wherein Q1 is C2-C10 alkenyl, C2-C10 alkynyl, C2-C10 haloalkenyl, C2-C10 haloalkynyl, C4-C10 cycloalkenyl, C4-C10 halocycloalkenyl, C2-C8 alkylcarbonyl or C2-C8 alkoxyalkyl.





Embodiment T3





    • A compound of Formula 1 wherein Q2 is a 4- or 7-membered heterocyclic ring or an 8- to 10-membered bicyclic ring system, each ring or ring system containing ring members selected from carbon atoms and 1 to 5 heteroatoms independently selected from up to 2 O, up to 2 S and up to 5 N atoms, wherein up to 3 carbon ring members are independently selected from C(═O) and C(═S), and the sulfur atom ring members are independently selected from S(═O)u(═NR8)v, each ring or ring system optionally substituted with up to 5 substituents independently selected from R7 on carbon atom ring members and selected from R9 on nitrogen atom ring members.





Embodiment T4





    • A compound of Formula 1 wherein Q2 is C2-C10 alkenyl, C2-C10 alkynyl, C2-C10 haloalkenyl, C2-C10 haloalkynyl, C4-C10 cycloalkenyl, C4-C10 halocycloalkenyl, C2-C8 alkylcarbonyl or C2-C8 alkoxyalkyl.





Embodiment T5





    • A compound of Formula 1 wherein J is —CR2R3—, —NR2a— or —O—.





Embodiment T6





    • A compound of Embodiment T5 wherein J is —CR2R3—.





Embodiment T7





    • A compound of Embodiment T5 wherein J is —NR2a—.





Embodiment T8





    • A compound of Embodiment T5 wherein J is —O—.





Embodiment T9





    • A compound of Formula 1 wherein R1 is cyano, formyl, C3-C8 alkylcarbonylalkyl, —C(C1-C4 alkyl)=N—O(C1-C4 alkyl), —C(O)NH2, C2-C6 cyanoalkyl, C3-C6 cycloalkyl; or arylcarbonyl, arylalkenylalkyl, arylcarbonylalkyl or —CPh=N—O(C1-C4 alkyl), each optionally substituted on ring members with up to 5 substituents independently selected from R13; or G1; or W1G1.





Embodiment T10





    • A compound of Embodiment T9 wherein each G1 is independently phenyl, or a 5- or 6-membered heterocyclic ring, each optionally substituted on ring members with up to 5 substituents independently selected from R13.





Embodiment T11





    • A compound of Embodiment T9 wherein W1 is C1-C3 alkylene, C2-C4 alkenylene, C2-C4 alkynylene, —(C1-C2 alkylene)C(═O)—, —C(═O)(C1-C2 alkylene)-, —CH2—, —CH2NH—, —OCH2—, —NCH2—, —N—, —O—, —S—, —SO— or —SO2— wherein the free bond projecting to the left indicates the connecting point of W1 to N and the free bond projecting to the right indicates the connecting point of W1 to G1.





Embodiment T12





    • A compound of Formula 1 wherein R2 and R3 are each independently hydroxy, C1-C4 haloalkyl or C1-C4 alkoxy.





Embodiment T13





    • A compound of Embodiment T7 wherein R2a is C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl or C1-C6 alkoxy.





Embodiment T14





    • A compound of Formula 1 wherein R1 and R2a are taken together as C3-C6 alkylene or —CH2OCH2—.





Embodiment T15





    • A compound of Formula 1 wherein R4 and R5 are each independently hydroxy, C1-C4 alkoxy or C1-C4 haloalkyl.





Embodiment T16





    • A compound of Formula 1 wherein R6 and Q2 are taken together with the nitrogen atom to which they are bonded to form an 8- to 10-membered bicyclic ring system, each ring or ring system containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 4 N atoms, wherein up to 3 carbon ring members are independently selected from C(═O) and C(═S), and the sulfur atom ring members are independently selected from S(═O)u(═NR8)v, each ring or ring system optionally substituted with up to 5 substituents independently selected from R7 on carbon atom ring members and selected from R9 on nitrogen atom ring members.





Embodiment T17





    • A compound of Formula 1 wherein each R7 and R10 is independently hydroxy, amino, C2-C8 alkoxyalkyl, C3-C8 alkoxyalkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 haloalkoxyhaloalkoxy, C3-C6 cycloalkyl, cyclopropylmethyl, 1-methylcyclopropyl, 2-methylcyclopropyl, C2-C8 alkylamino, C2-C8 dialkylamino, C2-C8 halodialkylamino or C3-C8 cycloalkylamino; or G2; or

    • each R7 is independently R26S(═O)═N—, R26S(═O)2NR25—C(═O)—, R26(R25N═)qS(═O)p—, wherein the free bond projecting to the right indicates the connecting point to Q1; or

    • each R10 is independently R17ON=CR17a—, (R18)2C═NO—, (R19)2NN═CR17a—, (R18)2C═NNR20a—, R20N=CR17a—, (R18)2C═N—, R17ON=CR17aC(R23b)2—, —(R18)2C═NOC(R24a)2—, R26S(═O)═N—, R26S(═O)2NR25—C(═O)— or R26(R25N═)qS(═O)p—, wherein the free bond projecting to the right indicates the connecting point to Q2.





Embodiment T18





    • A compound of Embodiment T17 wherein each p and q are independently 0, 1 or 2 in each instance of R26(R25N═)qS(═O)p—, provided that the sum of u and v is 0, 1 or 2 and when p is 0, q is other than 1 or 2.





Embodiment T19





    • A compound of Formula 1 wherein Y1 and Y2 are each independently NR12.





Embodiment T20





    • A compound of Embodiment T18 wherein each R12 is independently hydroxy, CHO, C2-C6 alkylcarbonyl or C2-C6 haloalkylcarbonyl.





Embodiment T21





    • A compound of Formula 1 wherein each G2 is a 5- or 6-membered heterocyclic ring, each optionally substituted on ring members with up to 5 substituents independently selected from R14.





Embodiment T22





    • A compound of Formula 1 wherein each R17 is independently H, C1-C6 alkyl, C3-C8 cycloalkyl, C4-C8 cycloalkylalkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C10 cycloalkylcarbonyl, C2-C8 alkoxycarbonyl, C2-C8 haloalkoxycarbonyl, C4-C10 cycloalkoxycarbonyl, C2-C8 alkylaminocarbonyl, C3-C10 dialkylaminocarbonyl, C4-C10 cycloalkylaminocarbonyl, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C3-C8 cycloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C1-C6 alkylaminosulfonyl, C2-C8 dialkylaminosulfonyl, C3-C10 trialkylsilyl or G1;
      • each R17a is independently H, C1-C6 alkyl, C3-C8 cycloalkyl, C4-C8 cycloalkylalkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3-C8 cycloalkylthio, C3-C10 trialkylsilyl or G1;
      • each R18 is independently H, hydroxy, C1-C6 alkyl, C3-C8 cycloalkyl, C4-C8 cycloalkylalkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C10 cycloalkylcarbonyl, C2-C8 alkoxycarbonyl, C2-C8 haloalkoxycarbonyl, C4-C10 cycloalkoxycarbonyl, C2-C8 alkylaminocarbonyl, C3-C10 dialkylaminocarbonyl, C4-C10 cycloalkylaminocarbonyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3-C8 cycloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C3-C8 cycloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C1-C6 alkylaminosulfonyl, C2-C8 dialkylaminosulfonyl, C3-C10 trialkylsilyl or G1;
      • each R19 is independently H, C1-C6 alkyl, C3-C8 cycloalkyl, C4-C8 cycloalkylalkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C10 cycloalkylcarbonyl, C2-C8 alkoxycarbonyl, C2-C8 haloalkoxycarbonyl, C4-C10 cycloalkoxycarbonyl, C2-C8 alkylaminocarbonyl, C3-C10 dialkylaminocarbonyl, C4-C10 cycloalkylaminocarbonyl, C1-C6 alkoxy, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C3-C8 cycloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C1-C6 alkylaminosulfonyl, C2-C8 dialkylaminosulfonyl, C3-C10 trialkylsilyl or G1;
      • each R20 is independently H, hydroxy, amino, C1-C6 alkyl, C3-C8 cycloalkyl, C4-C8cycloalkylalkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C10 cycloalkylcarbonyl, C2-C8 alkoxycarbonyl, C2-C8 haloalkoxycarbonyl, C4-C10 cycloalkoxycarbonyl, C2-C8 alkylaminocarbonyl, C3-C10 dialkylaminocarbonyl, C4-C10 cycloalkylaminocarbonyl, C1-C6 alkoxy, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C3-C8 cycloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C1-C6 alkylaminosulfonyl, C2-C8 dialkylaminosulfonyl, C3-C10 trialkylsilyl or G1:
      • each R20a is independently H, C1-C6 alkyl, C3-C8 cycloalkyl, C4-C8 cycloalkylalkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C1-C6 alkoxy, C3-C10 trialkylsilyl or G1;
      • each R23b is independently H, halogen, cyano, hydroxy, C1-C4 alkyl, C3-C8 cycloalkyl, C4-C8 cycloalkylalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkoxyalkyl, C2-C4 alkylcarbonyl, C2-C4 alkoxycarbonyl or C3-C6 cycloalkyl;
      • each R24a is independently H, C1-C4 alkyl, C3-C8 cycloalkyl, C4-C8 cycloalkylalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkoxyalkyl, C2-C4 alkylcarbonyl, C2-C4 alkoxycarbonyl or C3-C6 cycloalkyl;
      • each R25 is independently H, cyano, C2-C3 alkylcarbonyl or C2-C3 haloalkylcarbonyl;
      • each R26 is independently H, C1-C6 alkyl, C3-C8 cycloalkyl, C4-C8 cycloalkylalkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C1-C6 alkoxy, C3-C10 trialkylsilyl or G1.





Embodiment U1





    • A compound of Formula 1 wherein Q1 is other than a phenyl ring or a naphthalenyl ring system, each ring or ring system optionally substituted with up to 5 substituents independently selected from R7; or a 5- to 6-membered fully unsaturated heterocyclic ring or an 8- to 10-membered heteroaromatic bicyclic ring system, each ring or ring system containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 4 N atoms, wherein up to 3 carbon ring members are independently selected from C(═O) and C(═S), and the sulfur atom ring members are independently selected from S(═O)u(═NR8)v, each ring or ring system optionally substituted with up to 5 substituents independently selected from R7 on carbon atom ring members and selected from R9 on nitrogen atom ring members.





Embodiment U2





    • A compound of Formula 1 wherein Q2 is other than a phenyl ring or a naphthalenyl ring system, each ring or ring system optionally substituted with up to 5 substituents independently selected from R10; or a 5- to 6-membered fully unsaturated heterocyclic ring or an 8- to 10-membered heteroaromatic bicyclic ring system, each ring or ring system containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 4 N atoms, wherein up to 3 carbon ring members are independently selected from C(═O) and C(═S), and the sulfur atom ring members are independently selected from S(═O)u(═NR8)v, each ring or ring system optionally substituted with up to 5 substituents independently selected from R10 on carbon atom ring members and selected from R11 on nitrogen atom ring members.





Embodiment U3





    • A compound of Formula 1 wherein Y1 is other than O, S or NR12.





Embodiment U4





    • A compound of Formula 1 wherein Y2 is other than O, S or NR12.





Embodiment U5





    • A compound of Formula 1 wherein R1 is other than H, hydroxy, amino, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C4-C8 cycloalkylalkyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C10 cycloalkylcarbonyl, C2-C8 alkoxycarbonyl, C2-C8 haloalkoxycarbonyl, C4-C10 cycloalkoxycarbonyl, C2-C8 alkylaminocarbonyl, C3-C10 dialkylaminocarbonyl, C4-C10 cycloalkylaminocarbonyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3-C8 cycloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C3-C8 cycloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C1-C6 alkylaminosulfonyl, C2-C8 dialkylaminosulfonyl, C3-C10 trialkylsilyl or GI.





Embodiment U6





    • A compound of Formula 1 wherein R2 and R3, independently, are other than H, halogen or C1-C4 alkyl.





Embodiment U7





    • A compound of Formula 1 wherein R2 and R3 are taken together with the carbon atom to which they are bonded to form other than a C3-C7 cycloalkyl ring.





Embodiment U8





    • A compound of Formula 1 wherein R4 and R5, independently, are each other than H, halogen or C1-C4 alkyl.





Embodiment U9





    • A compound of Formula 1 wherein R6 is other than H, hydroxy, amino, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C10 cycloalkylcarbonyl, C2-C8 alkoxycarbonyl, C2-C8 haloalkoxycarbonyl, C4-C10 cycloalkoxycarbonyl, C2-C8 alkylaminocarbonyl, C3-C10 dialkylaminocarbonyl, C4-C10 cycloalkylaminocarbonyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3-C8 cycloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C3-C8 cycloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C1-C6 alkylaminosulfonyl, C2-C8 dialkylaminosulfonyl, C3-C10 trialkylsilyl or G1.





Embodiment U10





    • A compound of Formula 1 wherein each R7 and R10, independently, is other than halogen, cyano, nitro, C1-C8 alkyl, C1-C8 haloalkyl, C1-C8 nitroalkyl, C2-C8 alkenyl, C2-C8 haloalkenyl, C2-C8 nitroalkenyl, C2-C8 alkynyl, C2-C8 haloalkynyl, C4-C10 cycloalkylalkyl, C4-C10 halocycloalkylalkyl, C5-C12 alkylcycloalkylalkyl, C5-C12 cycloalkylalkenyl, C5-C12 cycloalkylalkynyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C4-C10 alkylcycloalkyl, C6-C12 cycloalkylcycloalkyl, C3-C8 cycloalkenyl, C3-C8 halocycloalkenyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C3-C8 haloalkoxyalkoxy, C3-C8 alkoxyalkoxy, C4-C10 cycloalkoxyalkyl, C3-C10 alkoxyalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylaminoalkyl, C2-C8 haloalkylaminoalkyl, C4-C10 cycloalkylaminoalkyl, C3-C10 dialkylaminoalkyl, —CHO, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C10 cycloalkylcarbonyl, —C(═O)OH, C2-C8 alkoxycarbonyl, C2-C8 haloalkoxycarbonyl, C4-C10 cycloalkoxycarbonyl, C5-C12 cycloalkylalkoxycarbonyl, —C(═O)NH2, C2-C8 alkylaminocarbonyl, C4-C10 cycloalkylaminocarbonyl, C3-C10 dialkylaminocarbonyl, C1-C8 alkoxy, C1-C8 haloalkoxy, C2-C8 alkoxyalkoxy, C2-C8 alkenyloxy, C2-C8 haloalkenyloxy, C3-C8 alkynyloxy, C3-C8 haloalkynyloxy, C3-C8 cycloalkoxy, C3-C8 halocycloalkoxy, C4-C10 cycloalkylalkoxy, C3-C10 alkylcarbonylalkoxy, C2-C8 alkylcarbonyloxy, C2-C8 haloalkylcarbonyloxy, C4-C10 cycloalkylcarbonyloxy, C1-C8 alkylsulfonyloxy, C1-C8 haloalkylsulfonyloxy, C1-C8 alkylthio, C1-C8 haloalkylthio, C3-C8 cycloalkylthio, C1-C8 alkylsulfinyl, C1-C8 haloalkylsulfinyl, C1-C8 alkylsulfonyl, C1-C8 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, formylamino, C2-C8 alkylcarbonylamino, C2-C8 haloalkylcarbonylamino, C2-C8 alkoxycarbonylamino, C1-C6 alkylsulfonylamino, C1-C6 haloalkylsulfonylamino, —SF5, —SCN, SO2NH2, C3-C12 trialkylsilyl, C4-C12 trialkylsilylalkyl, C4-C12 trialkylsilylalkoxy or G2.





Embodiment U11





    • A compound of Formula 1 wherein each R8 is other than H, cyano, C2-C3 alkylcarbonyl or C2-C3 haloalkylcarbonyl.





Embodiment U12





    • A compound of Formula 1 wherein each R9 and R11, independently, is other than cyano, C1-C3 alkyl, C2-C3 alkenyl, C2-C3 alkynyl, C3-C6 cycloalkyl, C2-C3 alkoxyalkyl, C1-C3 alkoxy, C2-C3 alkylcarbonyl, C2-C3 alkoxycarbonyl, C2-C3 alkylaminoalkyl or C3-C4 dialkylaminoalkyl.





Embodiment U13





    • A compound of Formula 1 wherein each R12 is other than H, cyano, C1-C4 alkyl, C1-C4 haloalkyl, —(C═O)CH3 or —(C═O)CF3





Embodiment U14





    • A compound of Formula 1 wherein each G1, independently, is other than phenyl, phenylmethyl (i.e. benzyl), pyridinylmethyl, phenylcarbonyl (i.e. benzoyl), phenoxy, phenylethynyl, phenylsulfonyl or a 5- or 6-membered heteroaromatic ring, each optionally substituted on ring members with up to 5 substituents independently selected from R13.





Embodiment U15





    • A compound of Formula 1 wherein each G2, independently, is other than phenyl, phenylmethyl (i.e. benzyl), pyridinylmethyl, phenylcarbonyl (i.e. benzoyl), phenoxy, phenylethynyl, phenylsulfonyl or a 5- or 6-membered heteroaromatic ring, each optionally substituted on ring members with up to 5 substituents independently selected from R14.





Embodiment U16





    • A compound of Formula 1 wherein each R13 and R14, independently, is other than halogen, cyano, hydroxy, amino, nitro, —CHO, —C(═O)OH, —C(═O)NH2, —SO2NH2, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C2-C8 alkoxycarbonyl, C4-C10 cycloalkoxycarbonyl, C5-C12 cycloalkylalkoxycarbonyl, C2-C8 alkylaminocarbonyl, C3-C10 dialkylaminocarbonyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C8 alkylcarbonyloxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C1-C6 alkylaminosulfonyl, C2-C8 dialkylaminosulfonyl, C3-C10 trialkylsilyl, C1-C6 alkylamino, C2-C8 dialkylamino, C2-C8 alkylcarbonylamino, C1-C6 alkylsulfonylamino, phenyl, pyridinyl or thienyl.





Embodiment U17





    • A compound of Formula 1 wherein each u and v, independently, is other than 0, 1 or 2 in each instance of S(═O)u(═NR8)v, provided that the sum of u and v is 0, 1 or 2.





Embodiment U18





    • A compound of Formula 1 other than wherein Y1 is O; Y2 is O; R1 is H; J is —CR2R3—; R2 is H; R3 is H; R4 is H; R5 is H, Q is Ph(3,4-di-F); Q2 is 1,3-benzodioxol-4-yl(2,2-di-F); and R6 is H.





Embodiment U19





    • A compound of Formula 1 other than wherein Y1 is O; Y2 is O; R1 is H; J is —CR2R3—; R2 is H; R3 is H; R4 is H; R5 is H, Q is 1,3-benzodioxol-5-yl(2,2-di-F); Q2 is Ph(2,3-di-F); and R6 is H.





Embodiment U20





    • A compound of Formula 1 other than wherein Y1 is O; Y2 is O; R1 is H; J is —CR2R3—; R2 is H; R3 is H; R4 is H; R5 is H, Q1 is 1,3-benzodioxol-5-yl(2,2-di-F); Q2 is Ph(2-F); and R6 is H.





Embodiment U21





    • A compound of Formula 1 other than wherein Y1 is O; Y2 is O; R1 is H; J is —CR2R3—; R2 is H; R3 is H; R4 is H; R5 is H, Q is 1,3-benzodioxol-5-yl(2,2-di-F); Q2 is Ph(2-CF3); and R6 is H.





Embodiment U22





    • A compound of Formula 1 other than wherein Y1 is O; Y2 is O; R1 is H; J is —CR2R3—; R2 is H; R3 is H; R4 is H; R5 is H, Q1 is 1,3-benzodioxol-5-yl(2,2-di-F); Q2 is Ph(2-F); and R6 is H.





Embodiment U23





    • A compound of Formula 1 other than wherein Y1 is O; Y2 is O; R1 is H; J is —CR2R3—; R2 is H; R3 is H; R4 is H; R5 is H, Q1 is 1,3-benzodioxol-5-yl(2,2-di-F); Q2 is Ph(2,3,4-tri-F); and R6 is H.





Embodiment U24





    • A compound of Formula 1 other than wherein Y1 is O; Y2 is O; R1 is Me; J is —CR2R3—; R2 is H; R3 is H; R4 is H; R5 is H, Q is Ph(3-CF3); Q2 is Ph(2-F); and R6 is H.





Embodiments of this disclosure, including Embodiments T1 through T22, Embodiments U1 through U24 above as well as any other embodiments (including Embodiments 1 through 91) as described herein, can be combined in any manner, and the descriptions of variables in the embodiments pertain not only to the compounds of Formula 1 but also to the starting compounds and intermediate compounds useful for preparing the compounds of Formula 1. In addition, embodiments of this disclosure, including Embodiments 1-91 above and Embodiments T1 through T22 and Embodiments U1 through U24 as well as any other embodiments described herein, and any combination thereof, pertain to the compositions and methods of the present disclosure.


Specific embodiments include compounds of Formula 1 selected from the group consisting of:

  • (3S,4S)—N-(2,3-difluorophenyl)-1-methyl-2-oxo-4-[4-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxamide (Compound 623);
  • (3S,4S)-4-(3,4-difluorophenyl)-N-(2-fluorophenyl)-1-methyl-2-oxo-3-pyrrolidinecarboxamide (Compound 596);
  • (3S,4S)—N-(2,3-difluorophenyl)-4-(3,4-difluorophenyl)-1-methyl-2-oxo-3-pyrrolidinecarboxamide (Compound 639); and
  • (3S,4S)—N-(2-fluorophenyl)-1-methyl-2-oxo-4-[4-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxamide (Compound 622).


Specific Embodiments include a compound of Formula 1 selected from the group consisting of Compound Numbers (where the Compound Number refers to the compound in Index Tables A, B, C, D, E or F): 353, 354, 355, 357, 358, 359, 360, 441, 442, 443, 444, 511, 524, 525, 684, 685, 714, 715 and 716.


This disclosure also relates to a method for controlling undesired vegetation comprising applying to the locus of the vegetation herbicidally effective amounts of the compounds of this disclosure (e.g., as a composition described herein). Of note as embodiments relating to methods of use are those involving the compounds of embodiments described above. Many compounds of this disclosure are particularly useful for selective control of weeds in crops such as wheat, barley, maize, soybean, sunflower, cotton, oilseed rape and rice, and specialty crops such as sugarcane, citrus, fruit and nut crops.


Also noteworthy as embodiments are herbicidal compositions of the present disclosure comprising the compounds of embodiments described above.


This disclosure also includes a herbicidal mixture comprising (a) a compound selected from Formula 1, N-oxides, and salts thereof, and (b) at least one additional active ingredient selected from (b1) photosystem II inhibitors, (b2) acetohydroxy acid synthase (AHAS) inhibitors, (b3) acetyl-CoA carboxylase (ACCase) inhibitors, (b4) auxin mimics, (b5) 5-enol-pyruvylshikimate-3-phosphate (EPSP) synthase inhibitors, (b6) photosystem I electron diverters, (b7) protoporphyrinogen oxidase (PPO) inhibitors, (b8) glutamine synthetase (GS) inhibitors, (b9) very long chain fatty acid (VLCFA) elongase inhibitors, (b10) auxin transport inhibitors, (b11) phytoene desaturase (PDS) inhibitors, (b12) 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitors, (b13) homogentisate solenesyltransererase (HST) inhibitors, (b14) cellulose biosynthesis inhibitors, (b15) other herbicides including mitotic disruptors, organic arsenicals, asulam, bromobutide, cinmethylin, cumyluron, dazomet, difenzoquat, dymron, etobenzanid, flurenol, fosamine, fosamine-ammonium, metam, methyldymron, oleic acid, oxaziclomefone, pelargonic acid and pyributicarb, and (b16) herbicide safeners; and salts of compounds of (b1) through (b16).


“Photosystem II inhibitors” (b1) are chemical compounds that bind to the D-1 protein at the QB-binding niche and thus block electron transport from QA to QB in the chloroplast thylakoid membranes. The electrons blocked from passing through photosystem II are transferred through a series of reactions to form toxic compounds that disrupt cell membranes and cause chloroplast swelling, membrane leakage, and ultimately cellular destruction. The QB-binding niche has three different binding sites: binding site A binds the triazines such as atrazine, triazinones such as hexazinone, and uracils such as bromacil, binding site B binds the phenylureas such as diuron, and binding site C binds benzothiadiazoles such as bentazon, nitriles such as bromoxynil and phenyl-pyridazines such as pyridate. Examples of photosystem II inhibitors include ametryn, amicarbazone, atrazine, bentazon, bromacil, bromofenoxim, bromoxynil, chlorbromuron, chloridazon, chlorotoluron, chloroxuron, cumyluron, cyanazine, daimuron, desmedipham, desmetryn, dimefuron, dimethametryn, diuron, ethidimuron, fenuron, fluometuron, hexazinone, ioxynil, isoproturon, isouron, lenacil, linuron, metamitron, methabenzthiazuron, metobromuron, metoxuron, metribuzin, monolinuron, neburon, pentanochlor, phenmedipham, prometon, prometryn, propanil, propazine, pyridafol, pyridate, siduron, simazine, simetryn, tebuthiuron, terbacil, terbumeton, terbuthylazine, terbutryn and trietazine. Of note is a compound of the disclosure mixed with atrazine, bromoxynil or metribuzin.


“AHAS inhibitors” (b2) are chemical compounds that inhibit acetohydroxy acid synthase (AHAS), also known as acetolactate synthase (ALS), and thus kill plants by inhibiting the production of the branched-chain aliphatic amino acids such as valine, leucine and isoleucine, which are required for protein synthesis and cell growth. Examples of AHAS inhibitors include amidosulfuron, azimsulfuron, bensulfuron-methyl, bispyribac-sodium, cloransulam-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, diclosulam, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, florasulam, flucarbazone-sodium, flumetsulam, flupyrsulfuron-methyl, flupyrsulfuron-sodium, foramsulfuron, halosulfuron-methyl, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron-methyl (including sodium salt), iofensulfuron (2-iodo-N-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]benzenesulfonamide), mesosulfuron-methyl, metazosulfuron (3-chloro-4-(5,6-dihydro-5-methyl-1,4,2-dioxazin-3-yl)-N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-1-methyl-1H-pyrazole-5-sulfonamide), metosulam, metsulfuron-methyl, nicosulfuron, oxasulfuron, penoxsulam, primisulfuron-methyl, propoxycarbazone-sodium, propyrisulfuron (2-chloro-N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-6-propylimidazo[1,2-b]pyridazine-3-sulfonamide), prosulfuron, pyrazosulfuron-ethyl, pyribenzoxim, pyriftalid, pyriminobac-methyl, pyrithiobac-sodium, rimsulfuron, sulfometuron-methyl, sulfosulfuron, thiencarbazone, thifensulfuron-methyl, triafamone (N-[2-[(4,6-dimethoxy-1,3,5-triazin-2-yl)carbonyl]-6-fluorophenyl]-1,1-difluoro-N-methylmethanesulfonamide), triasulfuron, tribenuron-methyl, trifloxysulfuron (including sodium salt), triflusulfuron-methyl and tritosulfuron. Of note is a compound of this disclosure mixed with nicosulfuron, flupyrsulfuron or chlorimuron.


“ACCase inhibitors” (b3) are chemical compounds that inhibit the acetyl-CoA carboxylase enzyme, which is responsible for catalyzing an early step in lipid and fatty acid synthesis in plants. Lipids are essential components of cell membranes, and without them, new cells cannot be produced. The inhibition of acetyl CoA carboxylase and the subsequent lack of lipid production leads to losses in cell membrane integrity, especially in regions of active growth such as meristems. Eventually shoot and rhizome growth ceases, and shoot meristems and rhizome buds begin to die back. Examples of ACCase inhibitors include alloxydim, butroxydim, clethodim, clodinafop, cycloxydim, cyhalofop, diclofop, fenoxaprop, fluazifop, haloxyfop, pinoxaden, profoxydim, propaquizafop, quizalofop, sethoxydim, tepraloxydim and tralkoxydim, including resolved forms such as fenoxaprop-P, fluazifop-P, haloxyfop-P and quizalofop-P and ester forms such as clodinafop-propargyl, cyhalofop-butyl, diclofop-methyl and fenoxaprop-P-ethyl. Of note is a compound of this disclosure mixed with pinoxaden or quizalofop.


Auxin is a plant hormone that regulates growth in many plant tissues. “Auxin mimics” (b4) are chemical compounds mimicking the plant growth hormone auxin, thus causing uncontrolled and disorganized growth leading to plant death in susceptible species. Examples of auxin mimics include aminocyclopyrachlor (6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid) and its methyl and ethyl esters and its sodium and potassium salts, aminopyralid, benazolin-ethyl, chloramben, clacyfos, clomeprop, clopyralid, dicamba, 2,4-D, 2,4-DB, dichlorprop, fluroxypyr, halauxifen (4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-2-pyridinecarboxylic acid), halauxifen-methyl (methyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-2-pyridinecarboxylate), MCPA, MCPB, mecoprop, picloram, quinclorac, quinmerac, 2,3,6-TBA, triclopyr, and methyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylate. Of note is a compound of this disclosure mixed with dicamba.


“EPSP synthase inhibitors” (b5) are chemical compounds that inhibit the enzyme, 5-enol-pyruvylshikimate-3-phosphate synthase, which is involved in the synthesis of aromatic amino acids such as tyrosine, tryptophan and phenylalanine. EPSP inhibitor herbicides are readily absorbed through plant foliage and translocated in the phloem to the growing points. Glyphosate is a relatively nonselective postemergence herbicide that belongs to this group. Glyphosate includes esters and salts such as ammonium, isopropylammonium, potassium, sodium (including sesquisodium) and trimesium (alternatively named sulfosate).


“Photosystem I electron diverters” (b6) are chemical compounds that accept electrons from Photosystem I, and after several cycles, generate hydroxyl radicals. These radicals are extremely reactive and readily destroy unsaturated lipids, including membrane fatty acids and chlorophyll. This destroys cell membrane integrity, so that cells and organelles “leak”, leading to rapid leaf wilting and desiccation, and eventually to plant death. Examples of this second type of photosynthesis inhibitor include diquat and paraquat.


“PPO inhibitors” (b7) are chemical compounds that inhibit the enzyme protoporphyrinogen oxidase, quickly resulting in formation of highly reactive compounds in plants that rupture cell membranes, causing cell fluids to leak out. Examples of PPO inhibitors include acifluorfen-sodium, azafenidin, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, cinidon-ethyl, fluazolate, flufenpyr-ethyl, flumiclorac-pentyl, flumioxazin, fluoroglycofen-ethyl, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil, pyraflufen-ethyl, saflufenacil, sulfentrazone, thidiazimin, trifludimoxazin (dihydro-1,5-dimehyl-6-thioxo-3-[2,2,7-trifluoro-3,4-dihydro-3-oxo-4-(2-propyn-1-yl)-2H-1,4-benzoxazin-6-yl]-1,3,5-triazine-2,4(1H,3H)-dione) and tiafenacil (methyl N-[2-[[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl]thio]-1-oxopropyl]-β-alaninate).


“GS inhibitors” (b8) are chemical compounds that inhibit the activity of the glutamine synthetase enzyme, which plants use to convert ammonia into glutamine. Consequently, ammonia accumulates and glutamine levels decrease. Plant damage probably occurs due to the combined effects of ammonia toxicity and deficiency of amino acids required for other metabolic processes. The GS inhibitors include glufosinate and its esters and salts such as glufosinate-ammonium and other phosphinothricin derivatives, glufosinate-P ((2S)-2-amino-4-(hydroxymethylphosphinyl)butanoic acid) and bilanaphos.


“VLCFA elongase inhibitors” (b9) are herbicides having a wide variety of chemical structures, which inhibit the elongase. Elongase is one of the enzymes located in or near chloroplasts which are involved in biosynthesis of VLCFAs. In plants, very-long-chain fatty acids are the main constituents of hydrophobic polymers that prevent desiccation at the leaf surface and provide stability to pollen grains. Such herbicides include acetochlor, alachlor, anilofos, butachlor, cafenstrole, dimethachlor, dimethenamid, diphenamid, fenoxasulfone (3-[[(2,5-dichloro-4-ethoxyphenyl)methyl]sulfonyl]-4,5-dihydro-5,5-dimethylisoxazole), fentrazamide, flufenacet, indanofan, mefenacet, metazachlor, metolachlor, naproanilide, napropamide, napropamide-M ((2R)—N,N-diethyl-2-(1-naphthalenyloxy)propanamide), pethoxamid, piperophos, pretilachlor, propachlor, propisochlor, pyroxasulfone, and thenylchlor, including resolved forms such as S-metolachlor and chloroacetamides and oxyacetamides. Of note is a compound of this disclosure mixed with flufenacet.


“Auxin transport inhibitors” (b10) are chemical substances that inhibit auxin transport in plants, such as by binding with an auxin-carrier protein. Examples of auxin transport inhibitors include diflufenzopyr, naptalam (also known as N-(1-naphthyl)phthalamic acid and 2-[(1-naphthalenylamino)carbonyl]benzoic acid).


“PDS inhibitors” (b1) are chemical compounds that inhibit carotenoid biosynthesis pathway at the phytoene desaturase step. Examples of PDS inhibitors include beflubutamid, diflufenican, fluridone, flurochloridone, flurtamone norflurzon and picolinafen.


“HPPD inhibitors” (b12) are chemical substances that inhibit the biosynthesis of synthesis of 4-hydroxyphenyl-pyruvate dioxygenase. Examples of HPPD inhibitors include benzobicyclon, benzofenap, bicyclopyrone (4-hydroxy-3-[[2-[(2-methoxyethoxy)methyl]-6-(trifluoromethyl)-3-pyridinyl]carbonyl]bicyclo[3.2.1]oct-3-en-2-one), fenquinotrione (2-[[8-chloro-3,4-dihydro-4-(4-methoxyphenyl)-3-oxo-2-quinoxalinyl]carbonyl]-1,3-cyclohexanedione), isoxachlortole, isoxaflutole, mesotrione, pyrasulfotole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate (1-[[1-ethyl-4-[3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoyl]-1H-pyrazol-5-yl]oxy]ethyl methyl carbonate), topramezone, 5-chloro-3-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-1-(4-methoxyphenyl)-2(1H)-quinoxalinone, 4-(2,6-diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone, 4-(4-fluorophenyl)-6-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-methyl-1,2,4-triazine-3,5(2H,4H)-dione, 5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-(3-methoxyphenyl)-3-(3-methoxypropyl)-4(3H)-pyrimidinone, 2-methyl-N-(4-methyl-1,2,5-oxadiazol-3-yl)-3-(methylsulfinyl)-4-(trifluoromethyl)benzamide and 2-methyl-3-(methylsulfonyl)-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzamide. Of note is a compound of this disclosure mixed with mesotrione or pyrasulfatole.


“HST inhibitors” (b13) disrupt a plant's ability to convert homogentisate to 2-methyl-6-solanyl-1,4-benzoquinone, thereby disrupting carotenoid biosynthesis. Examples of HST inhibitors include haloxydine, pyriclor, 3-(2-chloro-3,6-difluorophenyl)-4-hydroxy-1-methyl-1,5-naphthyridin-2(1H)-one, 7-(3,5-dichloro-4-pyridinyl)-5-(2,2-difluoroethyl)-8-hydroxypyrido[2,3-b]pyrazin-6(5H)-one and 4-(2,6-diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone.


HST inhibitors also include compounds of Formulae A and B.




embedded image


  • wherein Rd1 is H, Cl or CF3; Rd2 is H, C1 or Br; Rd3 is H or Cl; Rd4 is H, Cl or CF3; Rd5 is CH3, CH2CH3 or CH2CHF2; and Rd6 is OH, or —OC(═O)-i-Pr; and Re1 is H, F, Cl, CH3 or CH2CH3; Re2 is H or CF3; Re3 is H, CH3 or CH2CH3; Re4 is H, F or Br; Re5 is Cl, CH3, CF3, OCF3 or CH2CH3; Re6 is H, CH3, CH2CHF2 or C═CH; Re7 is OH, —OC(═O)Et, —OC(═O)-i-Pr or —OC(═O)-t-Bu; and Ae8 is N or CH.



“Cellulose biosynthesis inhibitors” (b14) inhibit the biosynthesis of cellulose in certain plants. They are most effective when applied preemergence or early postemergence on young or rapidly growing plants. Examples of cellulose biosynthesis inhibitors include chlorthiamid, dichlobenil, flupoxam, indaziflam (N2-[(1R,2S)-2,3-dihydro-2,6-dimethyl-1H-inden-1-yl]-6-(1-fluoroethyl)-1,3,5-triazine-2,4-diamine), isoxaben and triaziflam.


“Other herbicides” (b15) include herbicides that act through a variety of different modes of action such as mitotic disruptors (e.g., flamprop-M-methyl and flamprop-M-isopropyl), organic arsenicals (e.g., DSMA, and MSMA), 7,8-dihydropteroate synthase inhibitors, chloroplast isoprenoid synthesis inhibitors and cell-wall biosynthesis inhibitors. Other herbicides include those herbicides having unknown modes of action or do not fall into a specific category listed in (b1) through (b14) or act through a combination of modes of action listed above. Examples of other herbicides include aclonifen, asulam, amitrole, bromobutide, cinmethylin, clomazone, cumyluron, cyclopyrimorate (6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl 4-morpholinecarboxylate), daimuron, difenzoquat, etobenzanid, fluometuron, flurenol, fosamine, fosamine-ammonium, dazomet, dymron, ipfencarbazone (1-(2,4-dichlorophenyl)-N-(2,4-difluorophenyl)-1,5-dihydro-N-(1-methylethyl)-5-oxo-4H-1,2,4-triazole-4-carboxamide), metam, methyldymron, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb and 5-[[(2,6-difluorophenyl)methoxy]methyl]-4,5-dihydro-5-methyl-3-(3-methyl-2-thienyl)isoxazole.


“Herbicide safeners” (b16) are substances added to a herbicide formulation to eliminate or reduce phytotoxic effects of the herbicide to certain crops. These compounds protect crops from injury by herbicides but typically do not prevent the herbicide from controlling undesired vegetation. Examples of herbicide safeners include but are not limited to benoxacor, cloquintocet-mexyl, cumyluron, cyometrinil, cyprosulfamide, daimuron, dichlormid, dicyclonon, dietholate, dimepiperate, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen-ethyl, mefenpyr-diethyl, mephenate, methoxyphenone, naphthalic anhydride, oxabetrinil, N-(aminocarbonyl)-2-methylbenzenesulfonamide and N-(aminocarbonyl)-2-fluorobenzenesulfonamide, 1-bromo-4-[(chloromethyl)sulfonyl]benzene, 2-(dichloromethyl)-2-methyl-1,3-dioxolane (MG191), 4-(dichloroacetyl)-1-oxa-4-azospiro-[4.5]decane (MON 4660), 2,2-dichloro-1-(2,2,5-trimethyl-3-oxazolidinyl)-ethanone and 2-methoxy-N-[[4-[[(methylamino)carbonyl]amino]phenyl]sulfonyl]-benzamide. Of note is dietholate, 2,2-dichloro-1-(2,2,5-trimethyl-3-oxazolidinyl)-ethanone and 2-methoxy-N-[[4-[[(methylamino)carbonyl]amino]phenyl]sulfonyl]-benzamide (alternatively named N-(2-methoxybenzoyl)-4-[(methylaminocarbonyl)amino]benzenesulfonamide; CAS #129531-12-0). Of particular note is 2-methoxy-N-[[4-[[(methylamino)carbonyl]amino]phenyl]sulfonyl]-benzamide (alternatively named N-(2-methoxybenzoyl)-4-[(methylaminocarbonyl)amino]benzenesulfonamide; CAS #129531-12-0) mixed with any one of the compounds listed in Index Tables A, B, C, D, E or F.


The compounds of Formula 1 can be prepared by general methods known in the art of synthetic organic chemistry. Of note are the following methods described in Schemes 1-22 and variations thereof. The definitions of R1, R2, R2a, R3, R4, R5, R6, Q1, Q2, J, Y1, and Y2 in the compounds of Formulae 1 through 20 below are as defined above in the Summary unless otherwise noted. Formulae 1a-1h, 2b, 3a-3b, 4b, 5a, 5a′, 5a″ and 10a are various subsets of a compound of Formulae 1, 2, 3, 4, 5 and 10 respectively. Substituents for each subset formula are as defined for its parent formula unless otherwise noted.


As shown in Scheme 1 compounds of Formula 1a (i.e. Formula 1 wherein R1, R4 and R5 are H, Y1 and Y2 are O and J is —CR2R3—) can be prepared by reaction of acids of Formula 2 with amines of Formula 3 in the presence of a dehydrative coupling reagent such as propylphosphonic anhydride, dicyclohexylcarbodiimide, N-(3-dimethylaminopropyl)-N-ethylcarbodiimide, N,N-carbonyldiimidazole, 2-chloro-1,3-dimethylimidazolium chloride or 2-chloro-1-methylpyridinium iodide. Polymer-supported reagents, such as polymer-supported cyclohexylcarbodiimide, are also suitable. These reactions are typically run at temperatures ranging from 0-60° C. in a solvent such as dichloromethane, acetonitrile, N,N-dimethylformamide or ethyl acetate in the presence of a base such as triethylamine, N,N-diisopropylamine, or 1,8-diazabicyclo[5.4.0]undec-7-ene. See Organic Process Research & Development 2009, 13, 900-906 for coupling conditions employing propylphosphonic anhydride. The method of Scheme 1 utilizing propylphosphonic anhydride is illustrated by Step E of Synthesis Example 1. Substituents in the 3- and 4-positions of the pyrrolidinone ring of compounds of Formula 1a, i.e. C(O)N(Q2)(R6) and Q1, respectively, are predominantly in the trans configuration. In some instances, the presence of minor amounts of the cis isomer can be detected by NMR.




embedded image


As shown in Scheme 2 compounds of Formula 2 can be prepared by hydrolysis of esters of Formula 4 by methods well known to those skilled in the art. Hydrolysis is carried out with aqueous base or aqueous acid, typically in the presence of a co-solvent. Suitable bases for the reaction include, but are not limited to, hydroxides such as sodium and potassium hydroxide and carbonates such as sodium and potassium carbonate. Suitable acids for the reaction include, but are not limited to, inorganic acids such as hydrochloric acid, hydrobromic acid and sulfuric acid, and organic acids such as acetic acid and trifluoroacetic acid. A wide variety of co-solvents are suitable for the reaction including, but not limited to, methanol, ethanol and tetrahydrofuran. The reaction is conducted at temperatures ranging from −20° C. to the boiling point of the solvent, and typically from 0 to 100° C. The method of Scheme 2 is illustrated by Step D of Synthesis Example 1.




embedded image


As shown in Scheme 3, compounds of Formula 4 can be obtained by reduction of compounds of Formula 5 and subsequent in situ cyclization of the resulting intermediate amine. A wide variety of methods for reduction of the aliphatic nitro group in compounds of Formula 5 are known in the literature. Methods well known to those skilled in the art include catalytic hydrogenation in the presence of palladium on carbon or Raney nickel, iron or zinc metal in acidic medium (see, for example, Berichte der Deutschen Chemischen Gesellschaft 1904, 37, 3520-3525), and lithium aluminum hydride. Reduction can also be achieved with samarium(II) iodide in the presence of a proton source such as methanol (see for example, Tetrahedron Letters 1991, 32 (14), 1699-1702). Alternatively sodium borohydride in the presence of a nickel catalyst such as nickel(II) acetate or nickel(II) chloride can be used (see for example, Tetrahedron Letters 1985, 26 (52), 6413-6416). The method of Scheme 3 utilizing sodium borohydride in the presence of nickel(II) acetate is illustrated by Step C of Synthesis Example 1. Specific examples of a compound of Formula 4 that is useful in the preparation of a compound of Formula 1 can be found in Tables I through IV.




embedded image


As shown in Scheme 4, compounds of Formula 5 can be prepared by reacting diesters of Formula 6 with nitroalkanes of Formula 7, typically in the presence of a base. Suitable bases for the reaction include alkali metal lower alkoxides such as sodium methoxide in methanol or sodium ethoxide in ethanol. The method of Scheme 4 is illustrated by Step B of Synthesis Example 1. Compounds of Formula 6 can readily be prepared by methods known to those skilled in the art, e.g., by Knoevenagel condensation of aldehydes and malonates (see for example G. Jones, Organic Reactions Volume 15, John Wiley and Sons, 1967).




embedded image


Compounds of Formula 5a (i.e. Formula 5 wherein R2 and R3 are H) can be prepared by reacting nitroalkenes of Formula 8 with malonates of Formula 9 in the presence of a base as shown in Scheme 5. Suitable bases for this reaction include, but are not limited to, alkali metal lower alkoxides such as sodium methoxide in methanol or sodium ethoxide in ethanol, or bases such as lithium bis(trimethylsilyl)amide, sodium bis(trimethylsilyl)amide and lithium diisopropylamide in solvents such as tetrahydrofuran. Typically, the reaction is carried out in the range of from −78° C. to 23° C. See Synthesis 2005, 2239-2245 for conditions for effecting this transformation. Conditions for effecting this transformation in refluxing water in the absence of a catalyst have been reported in Synthetic Communications 2013, 43, 744-748. Nitroalkenes of Formula 8 can readily be prepared from aldehydes and nitromethane by methods known to those skilled in the art.




embedded image


Compounds of Formula 5a′ and 5a″ can be prepared stereoselectively by reacting nitroalkenes of Formula 8 with malonates of Formula 9 in the presence of a chiral catalyst and optionally in the presence of a suitable base as shown in Scheme 5A. Suitable catalysts include, but are not limited to Ni(II) with vicinal diamine ligands such as Ni(II) Bis[(R,R)—N,N′-dibenzylcyclohexane-1,2-diamine]dibromide, Ni(II) Bis[(S,S)—N,N-dibenzylcyclohexane-1,2-diamine]dibromide or nickel(II) bromide with chiral 1,1′-bi(tetrahydroisoquinoline) type diamines. Suitable organic bases for this reaction include, but are not limited to, piperidine, morpholine, triethylamine, 4-methylmorpholine or N,N-diisopropylethylamine. This transformation can be accomplished neat or in solvents such as tetrahydrofuran, toluene or dichloromethane. Typically, the reaction is carried out in the range of from −78° C. to 80° C. using 0 to 1 equivalent of catalyst and optionally 0 to 1 equivalent of a base. Conditions for effecting this transformation have been reported in J. Am. Chem. Soc. 2005, 9958-9959 or Eur. J. Org. Chem. 2011, 5441-5446 for conditions. Nitroalkenes of Formula 8 can readily be prepared from aldehydes and nitromethane by methods known to those skilled in the art.




embedded image


As shown in Scheme 6, compounds of Formula 1a can also be prepared by reductive cyclization of compounds of Formula 10 analogous to the method of Scheme 3. As also shown in Scheme 6, compounds of Formula 1b (i.e. Formula 1 wherein R1 is OH, R4 and R5 are H, and Y1 and Y2 are O) can be prepared from compounds of Formula 10 by catalytic transfer hydrogenation with ammonium formate in the presence of palladium on carbon, and subsequent in situ cyclization of the intermediate hydroxylamine. See J. Med. Chem. 1993, 36, 1041-1047 for catalytic transfer hydrogenation/cyclization conditions to produce N-hydroxypyrrolidinones. The method of Scheme 6 for preparing N-hydroxypyrrolidinones is illustrated by Step D of Synthesis Example 3.




embedded image


As shown in Scheme 7, compounds of Formula 10 can be prepared by reacting compounds of Formula 11 with nitroalkanes of Formula 7 in a solvent, in the presence of a base analogous to the method described in Scheme 4. The method of Scheme 7 is illustrated by Step C of Synthesis Example 3.




embedded image


As shown in Scheme 8, compounds of Formula 10a (i.e. Formula 10 wherein R2 and R3 are H) can be prepared, analogous to the method of Scheme 5, by reacting nitroalkenes of Formula 8 with malonates of Formula 12.




embedded image


As shown in Scheme 9, compounds of Formula 11 can be prepared by reaction of malonic amide Formula 12 with aldehydes of Formula 14 by methods known to those skilled in the art. As also shown in Scheme 9, malonates of Formula 12 can readily be prepared from lower alkyl malonyl chlorides of Formula 13 such as methyl malonyl chloride and amines of Formula 3 by methods known to those skilled in the art. The method of Scheme 9 is illustrated by Steps A and B of Synthesis Example 3.




embedded image


As shown in Scheme 10, mixtures of compounds of Formula 1e (i.e. Formula 1 wherein R1 and R5 are H, R4 is halogen and Y1 and Y2 are O) and Formula 1d (i.e. Formula 1 wherein R1 and R4 are H, R5 is halogen and Y1 and Y2 are O) can be prepared by reacting compounds of Formula 1a with a halogen source in a solvent, in the presence or absence of an initiator. Separation of the regioisomers produced in this reaction can be achieved by standard methods such as chromatography or fractional crystallization. Suitable halogen sources for this reaction include bromine, chlorine, N-chlorosuccinimide, N-bromosuccinimide and N-iodosuccinimide. Suitable initiators for this reaction include 2,2′-azobisisobutyronitrile (AIBN) and benzoyl peroxide. Typically, the reaction is carried out in solvents such as dichloromethane in the range of from 0° C. to the boiling point of the solvent. The method of Scheme 10 is illustrated by Synthesis Example 2.




embedded image


As shown in Scheme 11, compounds of Formula 1e (i.e. Formula 1 wherein R1 is NH2, R4 and R5 are H and Y1 and Y2 are O) can be prepared by reacting compounds of Formula 1a with an aminating reagent such as O-(diphenylphosphinyl)hydroxylamine and hydroxylamino-O-sulphonic acid. For procedures, conditions and reagents see Bioorganic & Medicinal Chemistry Letters 2009, 19, 5924-5926 and Journal of Organic Chemistry 2002, 67, 6236-6239.




embedded image


As shown in Scheme 12, compounds of Formula if (i.e. Formula 1 wherein R4, R5 and R6 are H and Y1 is O) can be produced by reaction of compounds of Formula 15 with isocyanates (i.e. Formula 16 wherein Y2 is O) or isothiocyanates (i.e. Formula 16 wherein Y2 is S) in the presence of base. Examples of the base which can be used for the present process include those listed for the method of Scheme 4. The reaction temperature can be selected from the range of from −78° C. to the boiling point of an inert solvent used. Typically, the reaction is carried out at temperatures ranging from −78° C. to 100° C. in solvents such as toluene.




embedded image


As shown in Scheme 13, compounds of Formula 15 can be prepared by reaction of compounds of Formula 17 with corresponding electrophiles of Formula 18 in the presence of base. In Formula 18, G denotes a leaving group, i.e. a nucleofuge. Depending upon selection of R1, suitable electrophiles for the reaction can include alkyl halides such as chlorides, bromides and iodides, alkylsulfonates, acid anhydrides such as tert-butoxycarbonyl anhydride and acetic anhydride, and haloalkylsilanes such as chlorotrimethylsilane. Suitable bases for the reaction include inorganic bases such as alkali or alkaline earth metal (e.g., lithium, sodium, potassium and cesium) hydroxides, alkoxides, carbonates, and phosphates, and organic bases such as triethylamine, N,N-diisopropylethylamine and 1,8-diazabicyclo[5.4.0]undec-7-ene. A wide variety of solvents are suitable for the reaction including, for example but not limited to, tetrahydrofuran, dichloromethane, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidinone, acetonitrile, C2-C6 alcohols and acetone as well as mixtures of these solvents. This reaction is conducted at temperatures ranging from −20 to 200° C., and typically between 0 and 50° C.




embedded image


As shown in Scheme 14, compounds of Formula 17 can be prepared by decarboxylation of acids of Formula 2 by methods well known to those skilled in the art. Decarboxylation is carried by heating compounds of Formula 2 in a solvent, typically in the presence of an acid. Suitable acids for the reaction include, but are not limited to, p-toluenesulfonic acid. A wide variety of co-solvents are suitable for the reaction including, but not limited to, toluene, isopropanol acetate and isobutyl methylketone. The reaction is conducted at temperatures ranging from −20° C. and to the boiling point of the solvent, and typically from 0 to 150° C. The method of Scheme 14 is illustrated by Step A of Synthesis Example 6.




embedded image


As shown in Scheme 15, compounds of Formula 1g (i.e. Formula 1 wherein R1 is H, R4 and R5 are H, and Y1 and Y2 are S) can be prepared by reacting compounds of Formula 1a with at least two equivalents of a thionation reagent such as Lawesson's reagent, tetraphosphorus decasulfide or diphosphorus pentasulfide in a solvent such as tetrahydrofuran or toluene. Typically, the reaction is carried out at temperatures ranging from 0 to 115° C. One skilled in the art recognizes that using less than two equivalents of the thionating reagent can provide mixtures comprising Formula 1 products wherein Y is O and Y2 is S, or Y1 is S and Y2 is O, which can be separated by conventional methods such as chromatography and crystallization.




embedded image


As shown in Scheme 16, compounds of Formula 1h (i.e. Formula 1 wherein R1, R4, R5 are H, Y2 is O and Y1 is NH) can be prepared by alkylation of compounds of Formula 1a triethyloxonium tetrafluoroborate (Meerwein's reagent) followed by treatment of the resulting imino ether of Formula 19 with aqueous ammonia. The method of Scheme 16 is illustrated by Steps A and B of Synthesis Example 4.




embedded image


As shown in Scheme 17, compounds of Formula 1b (i.e. Formula 1 wherein J is —NR2a— or —O—; R2a is H; R1, R4, R5 are H; and Y1 and Y2 are both 0) can be prepared from acids of Formula 2b using the method as described in Scheme 1.




embedded image


As shown in Scheme 18, a compound of Formula 2b can be prepared by hydrolysis of esters of Formula 4b by the method described in Scheme 2.




embedded image


As shown in Scheme 19, esters of Formula 4b can be prepared from diesters of Formula 6 and compounds of Formula 3a using a one step addition-cyclization procedure. The compounds of Formula 3a can be hydroxylamine, hydrazine or hydrazide derivatives. The reaction is carried out optionally in the presence of an acid or base and typically in the presence of a co-solvent. Suitable acids for the reaction include, but are not limited to, inorganic acids such as hydrochloric acid, hydrobromic acid and sulfuric acid, and organic acids such as acetic acid and trifluoroacetic acid. Suitable bases for the reaction include, but are not limited to, hydroxides such as sodium and potassium hydroxide, alkoxides such as sodium and potassium ethoxide, carbonates such as sodium and potassium carbonate, sodium hydride, metal amides such as lithium diisopropylamide and sodium hexamethyldisilazide and neutral nitrogen-containing bases such as triethylamine, N,N-diisopropylamine and 1,8-diazabicyclo[5.4.0]undec-7-ene. A wide variety of co-solvents are suitable for the reaction including, but not limited to, water, methanol, ethanol and tetrahydrofuran. The reaction is conducted at temperatures ranging from −20° C. to the boiling point of the solvent, and typically from 0 to 150° C. Diesters of Formula 6 can readily be prepared by Knoevenagel condensation of aldehydes and malonates (see for example G. Jones, Organic Reactions Volume 15, John Wiley and Sons, 1967).




embedded image


As shown in Scheme 20, the synthesis of a compound of Formula 4b can also be achieved by a two-step procedure proceeding through the formation and subsequent deprotetion/cyclization of an intermediate compound of Formula 20. A compound of Formula 20 can be obtained by carrying out the addition reaction of a compound of Formula 6 with an appropriate protected hydroxylamine, hydrazine or hydrazide derivative, optionally in the presence of an acid or base and typically in the presence of a co-solvent. Suitable protecting groups denoted as PG include, but are not limited to, tert-butyloxycarbonyl or carboxybenzyl. Suitable acids for the reaction include, but are not limited to, inorganic acids such as hydrochloric acid, hydrobromic acid and sulfuric acid, and organic acids such as acetic acid and trifluoroacetic acid. Suitable bases for the reaction include, but are not limited to, hydroxides such as sodium and potassium hydroxide, alkoxides such as sodium and potassium ethoxide, carbonates such as sodium and potassium carbonate, sodium hydride, metal amides such as lithium diisopropylamide and sodium hexamethyldisilazide and neutral nitrogen-containing bases such as triethylamine, N,N-diisopropylamine and 1,8-diazabicyclo[5.4.0]undec-7-ene. A wide variety of co-solvents are suitable for the reaction including, but not limited to, water, methanol, ethanol and tetrahydrofuran. The reaction is conducted at temperatures ranging from −20° C. to the boiling point of the solvent, and typically from 0 to 150° C. Deprotection of a compound of Formula 20 can be carried out by a method obvious to one skilled in the art. If the subsequent cyclization does not occur spontaneously upon deprotection, it can be carried out under the conditions listed above for the one step addition-cyclization.




embedded image


Alternatively, as shown in Schemes 21 and 22, a compound of Formula 1b can be prepared from amides of Formula 11 using the same methods as described in Schemes 19 and 20.




embedded image




embedded image


It is recognized by one skilled in the art that various functional groups can be converted into others to provide different compounds of Formula 1. For a valuable resource that illustrates the interconversion of functional groups in a simple and straightforward fashion, see Larock, R. C., Comprehensive Organic Transformations: A Guide to Functional Group Preparations, 2nd Ed., Wiley-VCH, New York, 1999. For example, intermediates for the preparation of compounds of Formula 1 may contain aromatic nitro groups, which can be reduced to amino groups, and then be converted via reactions well known in the art such as the Sandmeyer reaction, to various halides, providing compounds of Formula 1. The above reactions can also in many cases be performed in alternate order


It is recognized that some reagents and reaction conditions described above for preparing compounds of Formula 1 may not be compatible with certain functionalities present in the intermediates. In these instances, the incorporation of protection/deprotection sequences or functional group interconversions into the synthesis will aid in obtaining the desired products. The use and choice of the protecting groups will be apparent to one skilled in chemical synthesis (see, for example, Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd ed.; Wiley: New York, 1991). One skilled in the art will recognize that, in some cases, after the introduction of a given reagent as it is depicted in any individual scheme, it may be necessary to perform additional routine synthetic steps not described in detail to complete the synthesis of compounds of Formula 1. One skilled in the art will also recognize that it may be necessary to perform a combination of the steps illustrated in the above schemes in an order other than that implied by the particular presented to prepare the compounds of Formula 1.


One skilled in the art will also recognize that compounds of Formula 1 and the intermediates described herein can be subjected to various electrophilic, nucleophilic, radical, organometallic, oxidation, and reduction reactions to add substituents or modify existing substituents.


Without further elaboration, it is believed that one skilled in the art using the preceding description can utilize the present disclosure to its fullest extent. The following Examples are, therefore, to be construed as merely illustrative, and not limiting of the disclosure in any way whatsoever. Steps in the following Examples illustrate a procedure for each step in an overall synthetic transformation, and the starting material for each step may not have necessarily been prepared by a particular preparative run whose procedure is described in other Examples or Steps. Percentages are by weight except for chromatographic solvent mixtures or where otherwise indicated. Parts and percentages for chromatographic solvent mixtures are by volume unless otherwise indicated. 1H NMR spectra are reported in ppm downfield from tetramethylsilane in CDCl3 solution unless indicated otherwise; “s” means singlet, “d” means doublet, “t” means triplet, “q” means quartet, “n” means multiplet and “br s” means broad singlet. 19F NMR spectra are reported in ppm downfield from CFCl3 in CDCl3 unluess indicated otherwise. The enentiomeric ratio (ER) was determined by chiral high performance liquid chromatography analysis using a Chiralpak AD-RH column and eluting with a 50:50 isopropanol/water mixture at 40° C. at 0.3 mL/min.


Synthesis Example 1
Preparation of 4-(3-chloro-4-fluorophenyl)-2-oxo-N-[2-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxamide

(e.g. a compound of Formula 1 wherein Y1 and Y2 are both 0; J is —CR2R3—; R2 and R3 are both H; Q1 is Ph(3-C1,4-F); Q2 is Ph(2-CF3); R4 and R5 are both H; R6 is H; and R1 is H.)


Step A: Preparation of 1,3-diethyl 2-(3-chloro-4-fluorophenyl)methylene-propanedioate

A mixture of 3-chloro-4-fluorobenzaldehyde (3 g, 18.9 mmol), diethyl malonate (3.16 mL, 20.8 mmol), piperidine (0.37 mL, 3.8 mmol) and toluene (40 mL) was refluxed for 18 h with continuous removal of water (Dean-Stark trap). The cooled reaction mixture was concentrated under reduced pressure, and the residue was chromatographed on silica gel, eluted with 0% to 10% ethyl acetate in hexanes, to afford the title compound as a yellow oil (5 g).



1H NMR δ 7.61 (m, 1H), 7.61 (m, 1H), 7.53 (m, 1H), 7.35 (m, 1H), 7.15 (m, 1H), 4.33 (m, 4H), 1.33 (m, 6H).


Step B: Preparation 1,3-diethyl 2-[1-(3-chloro-4-fluorophenyl)-2-nitroethyl]-propanedioate

A mixture of 1,3-diethyl 2-(3-chloro-4-fluorophenyl)methylenepropanedioate (i.e. the product of Step A, 5 g, 16.7 mmol), nitromethane (8.9 mL, 166 mmol) and a methanol solution of sodium methoxide (25 wt %, 0.36 g, 1.67 mmol) in ethanol (60 mL) was stirred at 23° C. for 18 h. The reaction mixture was then concentrated under reduced pressure to afford a thick oil, which was diluted with 25% ethyl acetate in hexanes and filtered through a pad of Celite® diatomaceous filter aid to remove insoluble particulates. The filtrate was concentrated under reduced pressure to afford the title compound as a yellow oil (5.3 g).



1H NMR δ 7.32 (m, 1H), 7.15 (m, 1H), 7.10 (m, 1H), 4.87 (m, 2H), 4.22 (m, 3H), 4.07 (m, 2H), 3.76 (d, 1H), 1.27 (m, 3H), 1.12 (m, 3H).


Step C: Preparation of ethyl 4-(3-chloro-4-fluorophenyl)-2-oxo-3-pyrrolidine-carboxylate

A stirred mixture of 1,3-diethyl 2-[1-(3-chloro-4-fluorophenyl)-2-nitroethyl]-propanedioate (i.e. the product of Step B, 5.3 g, 14.7 mmol), nickel(II) acetate tetrahydrate (18.3 g, 73.4 mmol) and ethanol (120 mL) was cooled in an ice bath and treated with sodium borohydride (2.8 g, 73.4 mmol) in 0.5 g portions added over 5 minutes. The resulting mixture was stirred at 26° C. for 18 h. Saturated ammonium chloride solution (120 mL) and ethyl acetate (120 mL) were then added, the mixture was stirred for 1 h and then filtered through a pad of Celite® diatomaceous filter aid to remove insoluble particulates. The layers of the filtrate were separated, and the aqueous layer was extracted with ethyl acetate (2×100 mL). The combined organic extracts were washed with saturated ammonium chloride solution (100 mL), brine (100 mL), dried (MgSO4) and concentrated under reduced pressure to afford the title compound as a yellow-orange solid (4.73 g) which was used without purification.



1H NMR δ 7.31 (m, 1H), 7.12 (m, 2H), 6.93 (br s, 1H), 4.24 (m, 2H), 4.06 (m, 1H), 3.82 (m, 1H), 3.49 (d, 1H), 3.39 (m, 1H), 1.29 (m, 3H).


Step D: Preparation of 4-(3-chloro-4-fluorophenyl)-2-oxo-3-pyrrolidinecarboxylic acid

A mixture of ethyl 4-(3-chloro-4-fluorophenyl)-2-oxo-3-pyrrolidinecarboxylate (i.e. the product of Step C, 4.73 g, 16.5 mmol) and aqueous sodium hydroxide (50 wt %, 1.98 g, 49.5 mmol) in ethanol (50 mL) was stirred at 26° C. for 18 h. The reaction mixture was then diluted with water (50 mL) and extracted with diethyl ether (2×50 mL). The aqueous phase was acidified with concentrated hydrochloric acid to pH 2 and extracted with dichloromethane (3×50 mL). The combined dichloromethane extracts were washed with brine, dried (MgSO4), and concentrated under reduced pressure to afford the title compound as a white solid (2.37 g).



1H NMR (acetone-d6) δ 7.63 (m, 1H), 7.46 (m, 1H), 7.31 (m, 1H), 4.05 (m, 1H), 3.82 (m, 1H), 3.70 (d, 1H), 3.45 (m, 1H).


Step E: Preparation of 4-(3-chloro-4-fluorophenyl)-2-oxo-N-[2-(trifluoromethyl)-phenyl]-3-pyrrolidinecarboxamide

A mixture of 4-(3-chloro-4-fluorophenyl)-2-oxo-3-pyrrolidinecarboxylic acid (i.e. the product of Step D, 0.3 g, 1.17 mmol), triethylamine (0.49 mL, 3.5 mmol) and 2-(trifluoromethyl)aniline (0.16 mL, 1.28 mmol) in dichloromethane (8 mL) was stirred at ambient temperature for 30 minutes, and then treated with propylphosphonic anhydride in ethyl acetate (50%, 1.26 g, 1.98 mmol). The resulting mixture was stirred at ambient temperature for 18 h. The reaction mixture was then concentrated under reduced pressure, and the residue was chromatographed on silica gel, eluted with 0-30% ethyl acetate in hexanes, to afford a solid residue which on trituration with 1-chlorobutane afforded the title product, a compound of the present disclosure, as a light pink solid (0.2 g).



1H NMR δ 9.85 (s, 1H), 8.15 (m, 1H), 7.62 (m, 1H), 7.52 (m, 1H), 7.43 (m, 1H), 7.27 (m, 1H), 7.22 (m, 1H), 7.14 (m, 1H), 6.93 (s, 1H), 4.15 (m, 1H), 3.82 (m, 1H), 3.55 (d, 1H), 3.44 (m, 1H).


Synthesis Example 2
Preparation of 4-bromo-N-(2-fluorophenyl)-2-oxo-4-phenyl-3-pyrrolidinecarboxamide and 3-bromo-N-(2-fluorophenyl)-2-oxo-4-phenyl-3-pyrrolidinecarboxamide



  • (e.g. a compound of Formula 1 wherein Y1 and Y2 are both 0; J is —CR2R3—; R2 and R3 are both H; Q1 is Ph; Q2 is Ph(2-F); R4 is Br; R5 is H; R6 is H; and R1 is H.)



A mixture of 4-phenyl-2-oxo-N-(2-fluorophenyl)-3-pyrrolidinecarboxamide (prepared by the method of Example 1, 0.75 g, 2.5 mmol) in dichloromethane (25 mL) at room temperature was treated with bromine (0.16 mL, 3.0 mmol), and the resulting mixture was stirred for 18 h. The reaction mixture was then concentrated under reduced pressure, and the residue was chromatographed on silica gel, eluted with 0-2% methanol in dichloromethane, to give as the faster eluting product, 4-bromo-N-(2-fluorophenyl)-2-oxo-4-phenyl-3-pyrrolidinecarboxamide, a compound of the present disclosure, as a white solid (90 mg):



1H NMR δ 10.2 (br s, 1H), 8.00 (m, 1H), 7.28 (m, 5H), 7.02 (m, 3H), 6.45 (br s, 1H), 4.15 (d, 1H), 4.05 (m, 1H), 3.55 (d, 1H);


and the slower eluting product, 3-bromo-N-(2-fluorophenyl)-2-oxo-4-phenyl-3-pyrrolidine-carboxamide, a compound of the present disclosure, as a clear yellow oil (0.31 g):



1H NMR δ 9.55 (br s, 1H), 8.25 (t, 1H), 7.48 (d, 2H), 7.38 (m, 3H), 7.11 (m, 3H), 6.85 (br s, 1H), 4.45 (m, 1H), 3.77 (m, 1H), 3.65 (m, 1H).


Synthesis Example 3
Preparation of 4-(3,4-difluorophenyl)-N-(2-fluorophenyl)-1-hydroxy-2-oxo-3-pyrrolidinecarboxamide



  • (e.g. a compound of Formula 1 wherein Y1 and Y2 are both 0; J is —CR2R3—; R2 and R3 are both H; Q1 is Ph(3,4-di-F); Q2 is Ph(2-F); R4 and R5 are both H; R6 is H; and R1 is OH.)



Step A: Preparation of ethyl 3-[(2-fluorophenyl)amino]-3-oxopropanote

To a stirred solution of 2-fluoroaniline (10 g, 90.0 mmol) and triethylamine (9.1 g, 90.0 mmol) in dichloromethane (50 mL) at 0° C. was added dropwise over 10 minutes a solution of ethyl malonyl chloride (15.5 g, 90.0 mmol) in dichloromethane (30 mL). The resulting mixture was stirred at room temperature for 24 h. The reaction mixture was then poured into water (100 mL), and the organic layer was separated, washed with water (50 mL) and brine (50 mL), dried (MgSO4) and concentrated under reduced pressure to provide the title compound as an amber oil (19.0 g).



1H NMR δ 9.46 (br s, 1H), 8.28 (m, 1H), 7.1 (m, 2H), 4.26 (m, 2H), 3.51 (s, 2H), 1.32 (t, 3H).


Step B: Preparation of ethyl 3-(3,4-difluorophenyl)-2-[[(2-fluorophenyl)amino]-carbonyl]-2-propenoate

A solution of ethyl 3-[(2-fluorophenyl)amino]-3-oxopropanote (i.e. the product of Step A, 20.27 g, 90.0 mmol), 3,4-difluorobenzaldehyde (16.62 g, 117 mmol), acetic acid (2.6 mL, 45 mmol) and piperidine (0.89 mL, 9.0 mmol) in toluene (150 mL) was refluxed for 10 h with continuous removal of water (Dean-Stark trap). The reaction mixture was then cooled to room temperature and poured into water (100 mL). The organic layer was separated, and the water layer was extracted with ethyl acetate (3×50 mL). The combined organic extracts were washed with aqueous hydrochloric acid (1 N, 100 mL), dried (MgSO4) and concentrated under reduced pressure to give a solid residue. Recrystallization of the solid from diethyl ether (100 mL) afforded the title compound as a white solid (10.5 g).



1H NMR δ 8.26-8.48 (m, 1H), 8.15 (m, 1H), 7.74 (s, 1H), 7.51 (m, 1H), 7.35 (m, 1H), 7.11 (m, 4H), 4.35 (m, 2H), 1.36 (t, 3H).


Step C: Preparation of ethyl 3,4-difluoro-α-[[(2-fluorophenyl)amino]carbonyl]-β-(nitromethyl)benzenepropanoate

To a stirred suspension of ethyl 3-(3,4-difluorophenyl)-2-[[(2-fluorophenyl)amino]-carbonyl]-2-propenoate (i.e. the product of Step B, 4.42 g, 12.7 mmol) and nitromethane (17 mL, 317.5 mmol) at −20° C. was added 1,1,3,3-tetramethylguanidine (0.288 mL, 2.3 mmol). The mixture was stirred at −20° C. for 30 minutes, and then allowed to come to room temperature and stirred for an additional 2 h. The reaction mixture was diluted with dichloromethane (50 mL) and extracted with water (3×25 mL). The organic layer was dried (MgSO4) and concentrated under reduced pressure to provide a solid residue. The solid was chromatographed on silica gel, eluted with 0-100% ethyl acetate in hexane, to provide the title compound as a white solid (4.42 g).



1H NMR δ 8.6 (br s, 1H), 8.00-8.30 (m, 3H), 7.23 (m, 4H), 5.41 (m, 1H), 4.6 (m, 1H), 4.35 (m, 2H), 3.77-4.00 (m, 2H), 1.45 (m, 3H).


Step D: Preparation of 4-(3,4-difluorophenyl)-N-(2-fluorophenyl)-1-hydroxy-2-oxo-3-pyrrolidinecarboxamide

A mixture of ethyl 3,4-difluoro-α-[[(2-fluorophenyl)amino]carbonyl]-D-(nitromethyl)-benzenepropanoate (i.e. the product of Step C, 0.50 g, 1.22 mmol), 5% palladium on carbon (0.25 g) and methanol-ethyl acetate (1:1 by volume, 10 mL) was stirred at room temperature for 30 minutes, then cooled to at 0° C. and treated with ammonium formate (0.5 g). The resulting mixture was stirred for 1 h at room temperature. Additional 5% palladium on carbon (0.25 g) and ammonium formate (0.5 g) were added, and stirring at room temperature was continued for an additional 4 h. The reaction mixture was then filtered, and the filtrate was concentrated under reduced pressure to provide a residue, which was suspended in water (10 mL) and extracted with ethyl acetate (3×20 mL). The combined organic extracts were dried (MgSO4) and concentrated under reduced pressure to provide an oil, which on recrystallization from dichloromethane afforded the title product, a compound of the present disclosure, as a white solid (0.1 g).



1H NMR (DMSO-d6) δ 10.11 (br s, 2H), 8.00 (m, 1H), 7.71 (m, 1H), 7.42 (m, 1H), 7.33 (m, 3H), 7.1 (m, 1H), 4.25-3.61 (m, 4H).


Synthesis Example 4
Preparation of 2-amino-4-(3,4-difluorophenyl)-N-(2-fluorophenyl)dihydro-3H-pyrrole-3-carboxamide



  • (e.g. a compound of Formula 1 wherein Y1 is NH; Y2 is O; J is —CR2R3—; R2 and R3 are both H; Q1 is Ph(3,4-di-F); Q2 is Ph(2-F); R4 and R5 are both H; R6 is H; and R1 is H.)



Step A: Preparation of 4-(3,4-difluorophenyl)-N-(2-fluorophenyl)-2-oxo-3-pyrrolidinecarboxamide

To a stirred mixture of ethyl 3,4-difluoro-α-[[(2-fluorophenyl)amino]carbonyl]-β-(nitromethyl)benzenepropanoate (i.e. the product of Example 3 Step C, 3.346 g, 8.16 mmol) and nickel(I) acetate tetrahydrate (10.15 g, 40.8 mmol) in ethanol (50 mL) at 0° C., was added portionwise sodium borohydride (1.54 g, 40.8 mmol), and the resulting mixture was stirred at room temperature for 24 h. The reaction mixture was concentrated under reduced pressure, dissolved in ethyl acetate (100 mL) and washed successively with saturated ammonium chloride solution (50 mL), water (2×25 mL) and saturated sodium chloride (20 mL). The organic layer was dried (MgSO4) and concentrated under reduced pressure to provide a solid residue. The residue was chromatographed on silica gel, eluted with 0-100% ethyl acetate in hexane, to provide the title compound as a white solid (0.746 g).



1H NMR δ 9.67 (br s, 1H), 8.21 (m, 1H), 7.09 (m, 6H), 4.75 (br s, 1H), 4.21 (m, 1H), 3.82 (m, 1H), 3.52 (m, 1H), 3.43 (m, 1H).


Step B: Preparation of 4-(3,4-difluorophenyl)-N-(2-fluorophenyl)dihydro-2-methoxy-3H-pyrrole-3-carboxamide

A mixture of 4-(3,4-difluorophenyl)-N-(2-fluorophenyl)-2-oxo-3-pyrrolidine-carboxamide (i.e. the product of Step A, 0.187 g, 0.56 mmol) and trimethyloxonium tetrafluoroborate (0.083 g, 0.56 mmol) in dichloromethane (5 mL) was stirred under an atmosphere of nitrogen for 2 d. The reaction mixture was then treated with 1 N aqueous sodium hydroxide until basic (pH 10) and extracted with dichloromethane (3×5 mL). The organic layer was dried (MgSO4) and concentrated under reduced pressure to provide title compound as light yellow oil (0.138 g).



1H NMR δ 9.7 (br s, 1H), 8.62 (m, 1H), 8.25 (s, 1H), 7.26 (m, 4H), 7.00 (m, 1H), 4.26 (m, 2H), 4.00 (s, 3H), 3.42 (m, 2H).


Step C: Preparation of 2-amino-4-(3,4-difluorophenyl)-N-(2-fluorophenyl)dihydro-3H-pyrrole-3-carboxamide

A mixture of 4-(3,4-difluorophenyl)-N-(2-fluorophenyl)dihydro-2-methoxy-3H-pyrrole-3-carboxamide (i.e. the product Step B, 0.10 g, 0.287 mmol) and aqueous ammonium hydroxide (50%, 0.5 mL) in ethanol (2 mL) was heated in microwave apparatus for 10 minutes. The reaction mixture was concentrated under reduced pressure and the residue chromatographed on silica gel, eluted with 0-100% ethyl acetate/hexane, to afford the title product, a compound of the present disclosure, as a solid (0.016 g).



1H NMR δ 9.67 (br s, 1H), 8.21 (m, 1H), 7.27-7.01 (m, 6H), 6.50 (br s, 1H), 5.00 (br s, 1H), 4.26 (m, 1H), 3.82 (m, 1H), 3.55 (m, 1H), 3.43 (m, 1H).


Synthesis Example 5
Preparation of (3R,4S)—N-(2-fluorophenyl)-2-oxo-4-[3-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxamide



  • (e.g. a compound of Formula 1 wherein Y1 and Y2 are both 0; J is —CR2R3—; R2 and R3 are both H; Q1 is Ph(3-CF3); Q2 is Ph(2-F); R4 and R5 are both H; R6 is H; and R1 is H.)



Step A: Preparation of 1-[(E)-2-nitroethenyl]-3-(trifluoromethyl)benzene

To a stirred solution of 3-(trifluoromethyl)benzaldehyde (12.2 g, 70.1 mmol) in methanol (50 mL) was added nitromethane (4.34 g, 71.1 mmol). The mixture was cooled to 2° C. and sodium hydroxide (5.65 g, 70.6 mmol) was added as a 50% solution in 24.3 mL of water dropwise over 15 min. An exotherm was noted and additional ice was added to maintain the temperature below 10° C. while stirring for an additional 1 h. The reaction mixture was poured into 75 mL (75 mmol) of 1 N hydrochloric acid, rinsing the flask with 10 mL of methanol/water. The quenched reaction mixture was transferred to a separatory funnel and extracted with 150 mL of toluene. The aqueous layer was separated and concentrated under vacuum to yield 15.84 g of a yellow oil.


The intermediate thus obtained (15.84 g, 67.3 mmol) was taken up in 160 mL dichloromethane. The solution was cooled to 3° C. and methanesulfonyl chloride (8.03 g, 71.1 mmol) was added via pipette as a solution in 50 mL of dichloromethane. A solution of triethylamine (14.2 g, 140 mmol) in 50 mL of dichloromethane was then added dropwise over 50 min, and the resulting solution was stirred for 2 h. The reaction mixture was poured into 150 mL (150 mmol) of 1 N hydrochloric acid and transferred to a separatory funnel. The layers were separated and the organic layer was washed with 150 mL water and then filtered. The organic layer was concentrated under reduced pressure and the crude solid was tritrated with hexanes to yield 12.09 g of product as a yellow solid.



1H NMR (500 MHz) δ 7.54-7.66 (m, 2H) 7.69-7.84 (m, 3H) 7.96-8.08 (m, 1H).


Step B: Preparation of 1,3-diethyl 2-[(1S)-2-nitro-1-[3-(trifluoromethyl)phenyl]ethyl]propanedioate

To a stirred mixture of 1-[(E)-2-nitroethenyl]-3-(trifluoromethyl)benzene (i.e. the product of Step A, 3 g, 13.8 mmol) and diethyl malonate (3.319 g, 20.7 mmol) in toluene (1.5 mL) was added Ni(I) bis[(R,R)—N,N-dibenzylcyclohexane-1,2-diamine]bromide (prepared as described in J. Am. Chem. Soc. 2005, 127, 9958-9959; 0.111 g, 0.1 mmol). The resulting solution was stirred at 55° C. for 16 h. The solution was diluted with dichloromethane (20 mL) and concentrated under reduced pressure onto silica gel and purified by chromatography eluting with a gradient of ethyl acetate in hexanes (0 to 50%) to give 3.6 g of a light yellow oil. ER 94:6 (major eluting at 26.5 min, minor eluting at 20.3 min).



1H NMR (500 MHz) δ 7.54-7.60 (m, 1H), 7.43-7.48 (m, 2H), 7.51 (s, 1H), 4.83-5.00 (m, 2H), 4.17-4.35 (m, 3H), 3.98-4.06 (m, 2H), 3.77-3.85 (m, 1H), 1.20-1.29 (m, 3H), 0.99-1.10 (m 3H). 19F NMR (471 MHz) δ −62.78 (s, 3F). ESI [M−1] 376.3.


Step C: Preparation of ethyl (3R,4S)-2-oxo-4-[3-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxylate

A stirred mixture of 1,3-diethyl 2-[(1S)-2-nitro-1-[3-(trifluoromethyl)phenyl]ethyl]propanedioate (i.e. the product of Step B, 3.24 g, 8.48 mmol), nickel(II) chloride hexahydrate (2.01 g, 8.48 mmol) and ethanol (60 mL) was cooled in an ice bath and treated with sodium borohydride (0.97 g, 25.8 mmol) in 0.5 g portions added over 5 min. The resulting mixture was stirred at 26° C. for 18 h. Saturated ammonium chloride solution (120 mL) and ethyl acetate (120 mL) were then added, the mixture was stirred for 1 h and then filtered through a pad of Celite® diatomaceous filter aid to remove insoluble particulates. The layers of the filtrate were separated, and the aqueous layer was extracted with ethyl acetate (2×100 mL). The combined organic extracts were washed with saturated ammonium chloride solution (100 mL), brine (100 mL), dried (MgSO4) and concentrated under reduced pressure to afford the title compound as a thick yellow oil (2.66 g) which was used without purification.



1H NMR (500 MHz) δ 7.38-7.62 (m, 4H), 6.50 (br s, 1H), 4.21-4.31 (m, 2H), 4.15-4.21 (m, 1H), 3.82-3.92 (m, 1H), 3.51-3.58 (m, 1H), 3.37-3.50 (m, 1H), 1.27-1.34 (m, 3H). 19F NMR (471 MHz) δ −62.70 (s, 3F). ESI; [M+1]=302.0.


Step D: Preparation of (3R,4S)-2-oxo-4-[3-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxylic acid

A mixture of ethyl (3R,4S)-2-oxo-4-[3-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxylate (i.e. the product of Step C, 2.66 g, 8.8 mmol) and aqueous sodium hydroxide (50 wt %, 2.12 g, 26.5 mmol) in ethanol (30 mL) was stirred at 26° C. for 18 h. The reaction mixture was then diluted with water (50 mL) and extracted with diethyl ether (2×50 mL). The aqueous phase was acidified with concentrated hydrochloric acid to pH 2 and extracted with dichloromethane (3×50 mL). The combined dichloromethane extracts were washed with brine, dried (MgSO4), and concentrated under reduced pressure to afford the title compound as a white solid (2.05 g).



1H NMR (500 MHz, acetone-d6) δ 11.50 (br s, 1H), 7.70-7.89 (m, 2H), 7.56-7.68 (m, 2H), 7.45 (br s, 1H), 4.09-4.21 (m, 1H), 3.83-3.92 (m, 1H), 3.73-3.81 (m, 1H), 3.42-3.55 (m, 1H). 19F NMR (471 MHz, acetone-d6) δ −63.03 (s, 3F). ESI [M+1] 274.0.


Step E: Preparation of (3R,4S)—N-(2-fluorophenyl)-2-oxo-4-[3-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxamide

A mixture of (3R,4S)-2-oxo-4-[3-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxylic acid (i.e. the product of Step D, 2.0 g, 7.32 mmol), triethylamine (3.06 mL, 21.96 mmol) and 2-fluoroaniline (0.85 mL, 8.78 mmol) in dichloromethane (50 mL) was stirred at ambient temperature for 30 min, and then treated with propylphosphonic anhydride in ethyl acetate (50%, 7.92 g, 12.44 mmol). The resulting mixture was stirred at ambient temperature for 18 h. The reaction mixture was then concentrated under reduced pressure, and the residue was chromatographed on silica gel, eluted with 0-100% ethyl acetate in hexanes, to afford a solid residue which on trituration with 1-chlorobutane afforded the title product, a compound of the present disclosure, as a white solid (1.9 g). ER 88:12 (major eluting at 25.86 min, minor eluting at 17.66 min). Specific Rotation +74.71 at 23.4° C. at 589 nm, as a 1% solution (1 g/100 mL) in CHCl3.



1H NMR (500 MHz, acetone-d6) δ 10.05 (br s, 1H), 8.21-8.35 (m, 1H), 7.77-7.91 (m, 2H), 7.58-7.66 (m, 2H), 7.51 (br s, 1H), 7.02-7.22 (m, 3H), 4.18-4.30 (m, 1H), 3.94-4.04 (m, 1H), 3.84-3.93 (m, 1H), 3.42-3.53 (m, 1H).


Synthesis Example 6
Preparation of (3S,4S)—N-(2-fluorophenyl)-1-methyl-2-oxo-4-[3-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxamide



  • (e.g. a compound of Formula 1 wherein Y1 and Y2 are both 0; J is —CR2R3—; R2 and R3 are both H; Q1 is Ph(3-CF3); Q2 is Ph(2-F); R4 and R5 are both H; R6 is H; and R1 is Me.)



Step A Preparation of (4S)-4-[3-(trifluoromethyl)phenyl]-2-pyrrolidinone

A mixture of (3R,4S)-2-oxo-4-[3-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxylic acid (i.e. the product of Example 5, Step D, 1.5 g, 5.5 mmol) and toluene-4-sulfonic acid (0.010 g, 0.055 mmol) in toluene (12 mL) was stirred at 90° C. overnight. The reaction mixture was then concentrated under reduced pressure to afford a clear oil (1.29 g). The crude product was used without further purification.



1H NMR (500 MHz) δ 7.36-7.59 (m, 4H), 6.84 (br s, 1H), 3.70-3.88 (m, 2H), 3.35-3.50 (m, 1H), 2.72-2.87 (m, 1H), 2.44-2.58 (m, 1H). 19F NMR (471 MHz) δ −62.66 (s, 3F).


Step B: Preparation of (4S)-1-methyl-4-[3-(trifluoromethyl)phenyl]-2-pyrrolidinone

To a solution of (4S)-4-[3-(trifluoromethyl)phenyl]-2-pyrrolidinone (i.e. the product of Step A, 1.29 g, 5.6 mmol) in N,N-dimethylformamide (7 mL) was added sodium hydride (60% dispersion in mineral oil, 0.25 g, 6.2 mmol) in portions. The mixture was stirred for 10 min and then iodomethane (0.88 mL, 14.1 mmol) was added. The solution was stirred overnight at ambient temperature. The reaction mixture was diluted with water and extracted with diethyl ether (2×50 mL). The organic layer was washed with water, brine and then dried (MgSO4), filtered and concentrated under reduced pressure. The crude residue was chromatographed on silica gel, eluted with 0-20% ethyl acetate in dichloromethane, to afford a light brown oil (0.775 g).



1H NMR (500 MHz) δ 7.38-7.57 (m, 4H), 3.75-3.83 (m, 1H), 3.59-3.70 (m, 1H), 3.38-3.45 (m, 1H), 2.90-2.94 (m, 3H), 2.80-2.89 (m, 1H), 2.48-2.58 (m, 1H). 19F NMR (471 MHz) δ −62.67 (s, 3F).


Step C Preparation of (3R,4S)—N-(2-fluorophenyl)-1-methyl-2-oxo-4-[3-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxamide

A solution of (4S)-1-methyl-4-[3-(trifluoromethyl)phenyl]-2-pyrrolidinone (i.e. the product of Step B, 0.350 g, 1.44 mmol) in tetrahydrofuran (5 mL) was cooled to −78° C. To this mixture lithium bis(trimethylsilyl)amide (1.6 mL, 1.6 mmol as a 1 M solution in tetrahydrofuran) was added dropwise and the resulting solution was stirred for 30 min. Then 1-fluoro-2-isocyanatobenzene (0.17 mL, 1.44 mmol) was added dropwise and the solution was stirred for 2 h at −78° C. The reaction mixture was quenched with saturated aqueous ammonium chloride (10 mL), warmed to ambient temperature and the aqueous layer was extracted with ethyl acetate (3×25 mL). The organic layers were combined, washed with brine and then dried (MgSO4), filtered and concentrated under reduced pressure onto silica gel. The crude residue was chromatographed on silica gel, eluting with 0 to 40% ethyl acetate in hexanes, to afford a light pink solid (0.223 g).



1H NMR (500 MHz) δ 9.93 (br s, 1H), 8.15-8.27 (m, 1H), 7.38-7.65 (m, 4H), 6.93-7.15 (m, 3H), 4.10-4.23 (m, 1H), 3.72-3.88 (m, 1H), 3.56-3.68 (m, 1H), 3.39-3.53 (m, 1H), 2.90-3.06 (m, 3H). ESI [M+1] 381.0.


Synthesis Example 7
Preparation of 1,3-diethyl 2-[(1S)-1-(3,4-difluorophenyl)-2-nitro-ethyl]propanedioate



  • (e.g. an intermediate to prepare a compound of Formula 1 wherein Y1 and Y2 are both 0; J is —CR2R3—; R2 and R3 are H; Q1 is Ph(3,4-di-F); Q2 is Ph(2-F); R4 and R5 are both H; R6 is H; and R1 is H.)



Step A: Preparation of 1,3-diethyl 2-[(1S)-1-(3,4-difluorophenyl)-2-nitro-ethyl]propanedioate

To a stirred mixture of 1-[(E)-2-nitroethenyl]-3,4-difluorobenzene (prepared as described generally in WO2008/39882 A1, 1.67 g, 9.0 mmol) and diethyl malonate (1.73 g, 10.8 mmol) in toluene (10 mL) was added Ni(II) bis[(R,R)—N,N′-dibenzylcyclohexane-1,2-diamine]bromide (prepared as described in J. Am. Chem. Soc. 2005, 127, 9958-9959; 0.072 g, 0.1 mmol). The resulting solution was stirred at ambient temperature for 72 h. The solution was diluted with dichloromethane (20 mL) and concentrated under reduced pressure onto silica gel and purified by silica gel chromatography eluting with a gradient of ethyl acetate in hexanes (0 to 50%) to provide 2.18 g of a light yellow waxy solid. ER 96:4 (major eluting at 37.05 min, minor eluting at 27.09 min).



1H NMR (500 MHz) δ 7.06-7.16 (m, 2H), 6.95-7.03 (m, 1H), 4.73-4.94 (m, 2H), 4.16-4.29 (m, 3H), 4.01-4.10 (m, 2H), 3.71-3.79 (m, 1H), 1.22-1.30 (m, 3H), 1.07-1.15 (m, 3H). ESI [M+1]; 346.4


Synthesis Example 8
Preparation of (3RS,4RS)—N-(2,3-difluorophenyl)-1-methoxy-4-(4-methylphenyl)-2-oxo-pyrrolidine-3-carboxamide



  • (e.g. a compound of Formula 1 wherein Y1 and Y2 are both 0; J is —CR2R3—; R2 and R3 are both H; Q1 is Ph(4-Me); Q2 is Ph(2,3-diF); R4 and R5 are both H; R6 is H; and R1 is OMe.)



Step A: Preparation of ethyl (3RS,4SR)-1-hydroxy-4-(4-methylphenyl)-2-oxo-pyrrolidine-3-carboxylate

Ammonium formate (9.7 g, 150 mmol), followed by palladium (5% on carbon, 60% water; 6.7 g, 1.9 mmol), was added to a solution of diethyl 2-[1-(4-methylphenyl)-2-nitro-ethyl]-propanedioate (prepared using the method described in SYNTHESIS EXAMPLE 1, Step B; 6.1 g, 19 mmol) in tetrahydrofuran (57 ml) and methanol (13 ml) under nitrogen at ambient temperature. The reaction mixture was heated at 50° C. for 3.5 hours, then allowed to cool and filtered through Celite®. The filtrate was evaporated under reduced pressure and the residue purified by column chromatography to provide ethyl (3RS,4SR)-1-hydroxy-4-(4-methylphenyl)-2-oxo-pyrrolidine-3-carboxylate (2.69 g, 54%).



1H NMR δ=7.15 (m, 4H), 4.23 (m, 2H), 4.05 (m, 1H), 3.94 (q, 1H), 3.70 (dd, 1H), 3.57 (d, 1H), 2.34 (s, 3H), 1.27 (m, 3H) (N—OH not observed).


Step B: Preparation of ethyl (3RS,4SR)-1-methoxy-4-(4-methylphenyl)-2-oxo-pyrrolidine-3-carboxylate

A solution of trimethylsilyldiazomethane in hexanes (2.0 mol/l; 3.8 ml, 7.60 mmol) was added dropwise to a solution of ethyl (3RS,4SR)-1-hydroxy-4-(4-methylphenyl)-2-oxo-pyrrolidine-3-carboxylate (1.00 g, 3.80 mmol) in methanol (3.8 ml) and toluene (4.5 ml). The solution was stirred for 1 hour, acetic acid added dropwise until effervescence ceased, then the mixture was evaporated under reduced pressure and the residue purified by column chromatography to provide ethyl (3RS,4SR)-1-methoxy-4-(4-methylphenyl)-2-oxo-pyrrolidine-3-carboxylate (0.74 g, 70%).



1H NMR δ=7.15 (m, 4H), 4.23 (m, 2H), 4.00 (m, 1H), 3.90 (m, 1H), 3.85 (s, 3H), 3.53 (m, 1H), 3.47 (d, 1H), 2.33 (m 3H), 1.27 (m 3H).


Step C: Preparation of (3RS,4SR)-1-methoxy-4-(4-methylphenyl)-2-oxo-pyrrolidine-3-carboxylic acid

A solution of sodium hydroxide (0.32 g, 8.0 mmol) in water (2.7 ml) was added to a solution of ethyl (3RS,4SR)-1-methoxy-4-(4-methylphenyl)-2-oxo-pyrrolidine-3-carboxylate (0.74 g, 2.7 mmol) in ethanol (8.0 ml). The resulting mixture was stirred at ambient temperature for 1 hour, then water and ethyl acetate were added and the phases separated. The organic phase was extracted with water. The combined aqueous phases were washed with ethyl acetate, then acidified by the addition of hydrochloric acid and extracted with ethyl acetate. The organic extract was dried over magnesium sulphate, filtered and evaporated under reduced pressure to provide (3RS,4SR)-1-methoxy-4-(4-methylphenyl)-2-oxo-pyrrolidine-3-carboxylic acid (0.25 g, 38%), which was used without further purification.


Step D: Preparation of (3RS,4RS)—N-(2,3-difluorophenyl)-1-methoxy-4-(4-methylphenyl)-2-oxo-pyrrolidine-3-carboxamide

A solution of 1-propanphosphonic acid cyclic anhydride in ethyl acetate (50 mass %; 0.26 ml, 0.43 mmol) was added to a solution of (3RS,4SR)-1-methoxy-4-(4-methylphenyl)-2-oxo-pyrrolidine-3-carboxylic acid (0.063 g, 0.25 mmol) and 2,3-difluoroaniline (0.039 g, 0.30 mmol) in dichloromethane (1.8 ml), followed by the slow addition of diisopropylethylamine (0.13 ml, 0.76 mmol). The resulting mixture was stirred at ambient temperature for 17 hours, then water and aqueous sodium hydroxide added. The phases were separated and the organic was washed with hydrochloric acid, dried over magnesium sulphate, filtered and evaporated under reduced pressure. The residue was purified by column chromatography to provide (3RS,4RS)—N-(2,3-difluorophenyl)-1-methoxy-4-(4-methylphenyl)-2-oxo-pyrrolidine-3-carboxamide (0.063 g, 69%).



1H NMR δ=9.54 (br s, 1H), 8.00 (m, 1H), 7.26 (m, 2H), 7.18 (m, 2H), 7.00 (m, 1H), 6.89 (m, 1H), 4.01 (m 2H), 3.88 (s, 3H), 3.59 (m 2H), 2.34 (s, 3H).


Synthesis Example 9
Preparation of (3RS,4RS)-1-allyloxy-N-(2,3-difluorophenyl)-4-(4-methylphenyl)-2-oxo-pyrrolidine-3-carboxamide



  • (e.g. a compound of Formula 1 wherein Y1 and Y2 are both 0; J is —CR2R3—; R2 and R3 are both H; Q1 is Ph(4-Me); Q2 is Ph(2,3-diF); R4 and R5 are both H; R6 is H; and R1 is O-allyl.)



Step A: Preparation of (3RS,4SR)-1-hydroxy-4-(4-methylphenyl)-2-oxo-pyrrolidine-3-carboxylic acid

A solution of sodium hydroxide (0.046 g, 1.1 mmol) in water (0.38 ml) was added to a solution of ethyl (3RS,4SR)-1-hydroxy-4-(4-methylphenyl)-2-oxo-pyrrolidine-3-carboxylate (prepared as described in SYNTHESIS EXAMPLE 8, step A; 0.10 g, 0.38 mmol) in ethanol (1.1 ml). The resulting mixture was stirred at ambient temperature for 2 hours, then water and ethyl acetate were added. The phases were separated and the organic extracted with water. The combined aqueous layers were washed with ethyl acetate, acidified by the addition of hydrochloric acid and extracted with ethyl acetate. The organic extract was dried over magnesium sulphate, filtered and evaporated under reduced pressure to provide (3RS,4SR)-1-hydroxy-4-(4-methylphenyl)-2-oxo-pyrrolidine-3-carboxylic acid (0.063 g, 71%).



1H NMR δ=7.14 (s, 4H), 4.04 (m, 1H), 3.91 (m, 1H), 3.71 (m, 1H), 3.60 (m, 1H), 2.32 (s, 3H) (N—OH and CO2H not observed).


Step B: Preparation of (3RS,4SR)-1-allyloxy-4-(4-methylphenyl)-2-oxo-pyrrolidine-3-carboxylic acid

Sodium hydride (60 mass % in oil; 0.023 g, 0.59 mmol) and 3-iodoprop-1-ene (0.029 ml, 0.32 mmol) were added to a solution of (3RS,4SR)-1-hydroxy-4-(4-methylphenyl)-2-oxo-pyrrolidine-3-carboxylic acid (0.063 g, 0.27 mmol) in tetrahydrofuran (1.6 ml) under nitrogen. The resulting mixture was stirred at ambient temperature for 4 days, water added and the mixture extracted with ethyl acetate. The combined organic extracts were dried over magnesium sulphate, filtered and evaporated under reduced pressure to provide a residue that was purified by column chromatograph to provide (3RS,4SR)-1-allyloxy-4-(4-methylphenyl)-2-oxo-pyrrolidine-3-carboxylic acid (0.017 g, 23%).



1H NMR δ=7.16 (m, 4H), 6.02 (tdd, 1H), 5.40 (m, 2H), 4.52 (m, 2H), 3.90 (m, 2H), 3.57 (m, 1H), 3.51 (d, 1H), 2.32 (m 3H) (CO2H not observed).


Step C: Preparation of (3RS,4RS)-1-allyloxy-N-(2,3-difluorophenyl)-4-(4-methylphenyl)-2-oxo-pyrrolidine-3-carboxamide

A solution of 1-propanphosphonic acid cyclic anhydride in ethyl acetate (50 mass %; 0.062 ml, 0.10 mmol) was added to a solution of (3RS,4SR)-1-allyloxy-4-(4-methylphenyl)-2-oxo-pyrrolidine-3-carboxylic acid (0.017 g, 0.062 mmol) and 2,3-difluoroaniline (0.0096 g, 0.074 mmol) in dichloromethane (0.4 ml), followed by the slow addition of diisopropylethylamine (0.032 ml, 0.19 mmol). The resulting mixture was stirred at ambient temperature for 17 hours, then water and aqueous sodium hydroxide added. The phases were separated and the organic was washed with hydrochloric acid, dried over magnesium sulphate, filtered and evaporated under reduced pressure. The residue was purified by column chromatography to provide (3RS,4RS)-1-allyloxy-N-(2,3-difluorophenyl)-4-(4-methylphenyl)-2-oxo-pyrrolidine-3-carboxamide (0.022 g, 92%).



1H NMR δ=9.56 (br s, 1H), 8.00 (m, 1H), 7.22 (m, 4H), 7.00 (ddt, 1H), 6.88 (m, 1H), 6.05 (tdd, 1H), 5.40 (m, 2H), 4.55 (m, 2H), 4.03 (m, 1H), 3.95 (m, 1H), 3.60 (m, 1H), 3.54 (d, 1H), 2.34 (s, 3H).


Synthesis Example 10
Preparation of (3RS,4RS)—N-(2,3-difluorophenyl)-4-(4-methylphenyl)-2-oxo-1-prop-2-ynoxy-pyrrolidine-3-carboxamide



  • (e.g. a compound of Formula 1 wherein Y1 and Y2 are both 0; J is —CR2R3—; R2 and R3 are both H; Q1 is Ph(4-Me); Q2 is Ph(2,3-diF); R4 and R5 are both H; R6 is H; and R1 is O-propargyl.)



Step A: Preparation of ethyl (3RS,4SR)-4-(4-methylphenyl)-2-oxo-1-prop-2-ynoxy-pyrrolidine-3-carboxylate

Prop-2-yn-1-ol (0.027 ml, 0.46 mmol) and triphenylphosphine (0.14 g, 0.53 mmol) were added to a solution of ethyl (3RS,4SR)-1-hydroxy-4-(4-methylphenyl)-2-oxo-pyrrolidine-3-carboxylate (prepared as described in SYNTHESIS EXAMPLE 8, step A; 0.10 g, 0.38 mmol) in tetrahydrofuran (2.3 ml), then diisopropyl azodicarboxylate (0.097 ml, 0.49 mmol) was added dropwise. The resulting mixture was stirred at ambient temperature for 17 hours, then purified by column chromatography to provide ethyl (3RS,4SR)-4-(4-methylphenyl)-2-oxo-1-prop-2-ynoxy-pyrrolidine-3-carboxylate (0.069 g, 30%), which was used without further characterisation.


Step B: Preparation of (3RS,4RS)—N-(2,3-difluorophenyl)-4-(4-methylphenyl)-2-oxo-1-prop-2-ynoxy-pyrrolidine-3-carboxamide

2,3-Difluoroaniline (0.084 ml, 0.83 mmol) was added to a solution of ethyl (3RS,4SR)-4-(4-methylphenyl)-2-oxo-1-prop-2-ynoxy-pyrrolidine-3-carboxylate (0.050 g, 0.17 mmol) in dry dimethyl sulfoxide (0.50 ml) and the resulting solution was heated in a microwave oven at 160° C. for 10 minutes. The resulting mixture was allowed to cool and purified by column chromatography to provide (3RS,4RS)—N-(2,3-difluorophenyl)-4-(4-methylphenyl)-2-oxo-1-prop-2-ynoxy-pyrrolidine-3-carboxamide (0.006 g, 9%).



1H NMR δ=9.49 (br s, 1H), 8.00 (m, 1H), 7.27 (m, 2H), 7.19 (m, 2H), 7.01 (ddt, 1H), 6.88 (m, 1H), 4.72 (m, 2H), 4.11 (m, 2H), 3.74 (m, 1H), 3.56 (d, 1H), 2.60 (t, 1H), 2.34 (s, 3H).


Formulation/Utility


Compounds of this disclosure are generally useful as a herbicidal active ingredient in a composition, i.e. formulation, with at least one additional component selected from the group consisting of surfactants, solid diluents and liquid diluents, which serves as a carrier. The formulation or composition ingredients are selected to be consistent with the physical properties of the active ingredient, mode of application and environmental factors such as soil type, moisture and temperature.


Useful formulations include both liquid and solid compositions. Liquid compositions include solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions, oil-in-water emulsions, flowable concentrates and/or suspoemulsions) and the like, which optionally can be thickened into gels. The general types of aqueous liquid compositions are soluble concentrate, suspension concentrate, capsule suspension, concentrated emulsion, microemulsion, oil-in-water emulsion, flowable concentrate and suspo-emulsion. The general types of nonaqueous liquid compositions are emulsifiable concentrate, microemulsifiable concentrate, dispersible concentrate and oil dispersion.


The general types of solid compositions are dusts, powders, granules, pellets, prills, pastilles, tablets, filled films (including seed coatings) and the like, which can be water-dispersible (“wettable”) or water-soluble. Films and coatings formed from film-forming solutions or flowable suspensions are particularly useful for seed treatment. Active ingredient can be (micro)encapsulated and further formed into a suspension or solid formulation; alternatively the entire formulation of active ingredient can be encapsulated (or “overcoated”). Encapsulation can control or delay release of the active ingredient. An emulsifiable granule combines the advantages of both an emulsifiable concentrate formulation and a dry granular formulation. High-strength compositions are primarily used as intermediates for further formulation.


Sprayable formulations are typically extended in a suitable medium before spraying. Such liquid and solid formulations are formulated to be readily diluted in the spray medium, usually water, but occasionally another suitable medium like an aromatic or paraffinic hydrocarbon or vegetable oil. Spray volumes can range from about from about one to several thousand liters per hectare, but more typically are in the range from about ten to several hundred liters per hectare. Sprayable formulations can be tank mixed with water or another suitable medium for foliar treatment by aerial or ground application, or for application to the growing medium of the plant. Liquid and dry formulations can be metered directly into drip irrigation systems or metered into the furrow during planting.


The formulations will typically contain effective amounts of active ingredient, diluent and surfactant within the following approximate ranges which add up to 100 percent by weight.














Weight Percent











Active





Ingredient
Diluent
Surfactant





Water-Dispersible and Water-
0.001-90
0-99.999
0-15


soluble Granules, Tablets and





Powders





Oil Dispersions, Suspensions,
   1-50
40-99   
0-50


Emulsions, Solutions (including





Emulsifiable Concentrates)





Dusts
   1-25
70-99   
0-5 


Granules and Pellets
0.001-99
5-99.999
0-15


High Strength Compositions
  90-99
0-10   
0-2 









Solid diluents include, for example, clays such as bentonite, montmorillonite, attapulgite and kaolin, gypsum, cellulose, titanium dioxide, zinc oxide, starch, dextrin, sugars (e.g., lactose, sucrose), silica, talc, mica, diatomaceous earth, urea, calcium carbonate, sodium carbonate and bicarbonate, and sodium sulfate. Typical solid diluents are described in Watkins et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, N.J.


Liquid diluents include, for example, water, N,N-dimethylalkanamides (e.g., N,N-dimethylformamide), limonene, dimethyl sulfoxide, N-alkylpyrrolidones (e.g., N-methylpyrrolidinone), alkyl phosphates (e.g., triethyl phosphate), ethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, propylene carbonate, butylene carbonate, paraffins (e.g., white mineral oils, normal paraffins, isoparaffins), alkylbenzenes, alkylnaphthalenes, glycerine, glycerol triacetate, sorbitol, aromatic hydrocarbons, dearomatized aliphatics, alkylbenzenes, alkylnaphthalenes, ketones such as cyclohexanone, 2-heptanone, isophorone and 4-hydroxy-4-methyl-2-pentanone, acetates such as isoamyl acetate, hexyl acetate, heptyl acetate, octyl acetate, nonyl acetate, tridecyl acetate and isobornyl acetate, other esters such as alkylated lactate esters, dibasic esters, alkyl and aryl benzoates and γ-butyrolactone, and alcohols, which can be linear, branched, saturated or unsaturated, such as methanol, ethanol, n-propanol, isopropyl alcohol, n-butanol, isobutyl alcohol, n-hexanol, 2-ethylhexanol, n-octanol, decanol, isodecyl alcohol, isooctadecanol, cetyl alcohol, lauryl alcohol, tridecyl alcohol, oleyl alcohol, cyclohexanol, tetrahydrofurfuryl alcohol, diacetone alcohol, cresol and benzyl alcohol. Liquid diluents also include glycerol esters of saturated and unsaturated fatty acids (typically C6-C22), such as plant seed and fruit oils (e.g., oils of olive, castor, linseed, sesame, corn (maize), peanut, sunflower, grapeseed, safflower, cottonseed, soybean, rapeseed, coconut and palm kernel), animal-sourced fats (e.g., beef tallow, pork tallow, lard, cod liver oil, fish oil), and mixtures thereof. Liquid diluents also include alkylated fatty acids (e.g., methylated, ethylated, butylated) wherein the fatty acids may be obtained by hydrolysis of glycerol esters from plant and animal sources, and can be purified by distillation. Typical liquid diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950.


The solid and liquid compositions of the present disclosure often include one or more surfactants. When added to a liquid, surfactants (also known as “surface-active agents”) generally modify, most often reduce, the surface tension of the liquid. Depending on the nature of the hydrophilic and lipophilic groups in a surfactant molecule, surfactants can be useful as wetting agents, dispersants, emulsifiers or defoaming agents.


Surfactants can be classified as nonionic, anionic or cationic. Nonionic surfactants useful for the present compositions include, but are not limited to: alcohol alkoxylates such as alcohol alkoxylates based on natural and synthetic alcohols (which may be branched or linear) and prepared from the alcohols and ethylene oxide, propylene oxide, butylene oxide or mixtures thereof; amine ethoxylates, alkanolamides and ethoxylated alkanolamides; alkoxylated triglycerides such as ethoxylated soybean, castor and rapeseed oils; alkylphenol alkoxylates such as octylphenol ethoxylates, nonylphenol ethoxylates, dinonyl phenol ethoxylates and dodecyl phenol ethoxylates (prepared from the phenols and ethylene oxide, propylene oxide, butylene oxide or mixtures thereof); block polymers prepared from ethylene oxide or propylene oxide and reverse block polymers where the terminal blocks are prepared from propylene oxide; ethoxylated fatty acids; ethoxylated fatty esters and oils; ethoxylated methyl esters; ethoxylated tristyrylphenol (including those prepared from ethylene oxide, propylene oxide, butylene oxide or mixtures thereof); fatty acid esters, glycerol esters, lanolin-based derivatives, polyethoxylate esters such as polyethoxylated sorbitan fatty acid esters, polyethoxylated sorbitol fatty acid esters and polyethoxylated glycerol fatty acid esters; other sorbitan derivatives such as sorbitan esters; polymeric surfactants such as random copolymers, block copolymers, alkyd peg (polyethylene glycol) resins, graft or comb polymers and star polymers; polyethylene glycols (pegs); polyethylene glycol fatty acid esters; silicone-based surfactants; and sugar-derivatives such as sucrose esters, alkyl polyglycosides and alkyl polysaccharides.


Useful anionic surfactants include, but are not limited to: alkylaryl sulfonic acids and their salts; carboxylated alcohol or alkylphenol ethoxylates; diphenyl sulfonate derivatives; lignin and lignin derivatives such as lignosulfonates; maleic or succinic acids or their anhydrides; olefin sulfonates; phosphate esters such as phosphate esters of alcohol alkoxylates, phosphate esters of alkylphenol alkoxylates and phosphate esters of styryl phenol ethoxylates; protein-based surfactants; sarcosine derivatives; styryl phenol ether sulfate; sulfates and sulfonates of oils and fatty acids; sulfates and sulfonates of ethoxylated alkylphenols; sulfates of alcohols; sulfates of ethoxylated alcohols; sulfonates of amines and amides such as N,N-alkyltaurates; sulfonates of benzene, cumene, toluene, xylene, and dodecyl and tridecylbenzenes; sulfonates of condensed naphthalenes; sulfonates of naphthalene and alkyl naphthalene; sulfonates of fractionated petroleum; sulfosuccinamates; and sulfosuccinates and their derivatives such as dialkyl sulfosuccinate salts.


Useful cationic surfactants include, but are not limited to: amides and ethoxylated amides; amines such as N-alkyl propanediamines, tripropylenetriamines and dipropylenetetramines, and ethoxylated amines, ethoxylated diamines and propoxylated amines (prepared from the amines and ethylene oxide, propylene oxide, butylene oxide or mixtures thereof); amine salts such as amine acetates and diamine salts; quaternary ammonium salts such as quaternary salts, ethoxylated quaternary salts and diquaternary salts; and amine oxides such as alkyldimethylamine oxides and bis-(2-hydroxyethyl)-alkylamine oxides.


Also useful for the present compositions are mixtures of nonionic and anionic surfactants or mixtures of nonionic and cationic surfactants. Nonionic, anionic and cationic surfactants and their recommended uses are disclosed in a variety of published references including McCutcheon's Emulsifiers and Detergents, annual American and International Editions published by McCutcheon's Division, The Manufacturing Confectioner Publishing Co.; Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964; and A. S. Davidson and B. Milwidsky, Synthetic Detergents, Seventh Edition, John Wiley and Sons, New York, 1987.


Compositions of this disclosure may also contain formulation auxiliaries and additives, known to those skilled in the art as formulation aids (some of which may be considered to also function as solid diluents, liquid diluents or surfactants). Such formulation auxiliaries and additives may control: pH (buffers), foaming during processing (antifoams such polyorganosiloxanes), sedimentation of active ingredients (suspending agents), viscosity (thixotropic thickeners), in-container microbial growth (antimicrobials), product freezing (antifreezes), color (dyes/pigment dispersions), wash-off (film formers or stickers), evaporation (evaporation retardants), and other formulation attributes. Film formers include, for example, polyvinyl acetates, polyvinyl acetate copolymers, polyvinylpyrrolidone-vinyl acetate copolymer, polyvinyl alcohols, polyvinyl alcohol copolymers and waxes. Examples of formulation auxiliaries and additives include those listed in McCutcheon's Volume 2: Functional Materials, annual International and North American editions published by McCutcheon's Division, The Manufacturing Confectioner Publishing Co.; and PCT Publication WO 03/024222.


The compound of Formula 1 and any other active ingredients are typically incorporated into the present compositions by dissolving the active ingredient in a solvent or by grinding in a liquid or dry diluent. Solutions, including emulsifiable concentrates, can be prepared by simply mixing the ingredients. If the solvent of a liquid composition intended for use as an emulsifiable concentrate is water-immiscible, an emulsifier is typically added to emulsify the active-containing solvent upon dilution with water. Active ingredient slurries, with particle diameters of up to 2,000 μm can be wet milled using media mills to obtain particles with average diameters below 3 μm. Aqueous slurries can be made into finished suspension concentrates (see, for example, U.S. Pat. No. 3,060,084) or further processed by spray drying to form water-dispersible granules. Dry formulations usually require dry milling processes, which produce average particle diameters in the 2 to 10 μm range. Dusts and powders can be prepared by blending and usually grinding (such as with a hammer mill or fluid-energy mill). Granules and pellets can be prepared by spraying the active material upon preformed granular carriers or by agglomeration techniques. See Browning, “Agglomeration”, Chemical Engineering, Dec. 4, 1967, pp 147-48, Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57 and following, and WO 91/13546. Pellets can be prepared as described in U.S. Pat. No. 4,172,714. Water-dispersible and water-soluble granules can be prepared as taught in U.S. Pat. Nos. 4,144,050, 3,920,442 and DE 3,246,493. Tablets can be prepared as taught in U.S. Pat. Nos. 5,180,587, 5,232,701 and 5,208,030. Films can be prepared as taught in GB 2,095,558 and U.S. Pat. No. 3,299,566.


For further information regarding the art of formulation, see T. S. Woods, “The Formulator's Toolbox—Product Forms for Modern Agriculture” in Pesticide Chemistry and Bioscience, The Food-Environment Challenge, T. Brooks and T. R. Roberts, Eds., Proceedings of the 9th International Congress on Pesticide Chemistry, The Royal Society of Chemistry, Cambridge, 1999, pp. 120-133. See also U.S. Pat. No. 3,235,361, Col. 6, line 16 through Col. 7, line 19 and Examples 10-41; U.S. Pat. No. 3,309,192, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182; U.S. Pat. No. 2,891,855, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4; Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961, pp 81-96; Hance et al., Weed Control Handbook, 8th Ed., Blackwell Scientific Publications, Oxford, 1989; and Developments in formulation technology, PJB Publications, Richmond, U K, 2000.


In the following Examples, all percentages are by weight and all formulations are prepared in conventional ways. Compound numbers refer to compounds in Index Tables A-F. Without further elaboration, it is believed that one skilled in the art using the preceding description can utilize the present disclosure to its fullest extent. The following Examples are, therefore, to be construed as merely illustrative, and not limiting of the disclosure in any way whatsoever. Percentages are by weight except where otherwise indicated.


Example A











High Strength Concentrate


















Compound352
98.5%



silica aerogel
0.5%



synthetic amorphous fine silica
1.0%









Example B











Wettable Powder


















Compound 352
65.0%



dodecylphenol polyethylene glycol ether
2.0%



sodium ligninsulfonate
4.0%



sodium silicoaluminate
6.0%



montmorillonite (calcined)
23.0%









Example C











Granule
















Compound 352
10.0%


attapulgite granules (low volatile matter, 0.71/0.30 mm;
90.0%


U.S.S. No. 25-50 sieves)









Example D











Extruded Pellet


















Compound 352
25.0%



anhydrous sodium sulfate
10.0%



crude calcium ligninsulfonate
5.0%



sodium alkylnaphthalenesulfonate
1.0%



calcium/magnesium bentonite
59.0%









Example E











Emulsifiable Concentrate


















Compound 352
10.0%



polyoxyethylene sorbitol hexoleate
20.0%



C6-C10 fatty acid methyl ester
70.0%









Example F











Microemulsion


















Compound 352
5.0%



polyvinylpyrrolidone-vinyl acetate copolymer
30.0%



alkylpolyglycoside
30.0%



glyceryl monooleate
15.0%



water
20.0%









Example G











Suspension Concentrate


















Compound 352
 35%



butyl polyoxyethylene/polypropylene block copolymer
4.0%



stearic acid/polyethylene glycol copolymer
1.0%



styrene acrylic polymer
1.0%



xanthan gum
0.1%



propylene glycol
5.0%



silicone based defoamer
0.1%



1,2-benzisothiazolin-3-one
0.1%



water
53.7% 









Example H











Emulsion in Water


















Compound 352
10.0%



butyl polyoxyethylene/polypropylene block copolymer
4.0%



stearic acid/polyethylene glycol copolymer
1.0%



styrene acrylic polymer
1.0%



xanthan gum
0.1%



propylene glycol
5.0%



silicone based defoamer
0.1%



1,2-benzisothiazolin-3-one
0.1%



aromatic petroleum based hydrocarbon
20.0



water
58.7%









Example I











Oil Dispersion


















Compound 352
25%



polyoxyethylene sorbitol hexaoleate
15%



organically modified bentonite clay
2.5% 



fatty acid methyl ester
57.5%









Example J











Suspoemulsion


















Compound 352
10.0%



imidacloprid
5.0%



butyl polyoxyethylene/polypropylene block copolymer
4.0%



stearic acid/polyethylene glycol copolymer
1.0%



styrene acrylic polymer
1.0%



xanthan gum
0.1%



propylene glycol
5.0%



silicone based defoamer
0.1%



1,2-benzisothiazolin-3-one
0.1%



aromatic petroleum based hydrocarbon
20.0%



water
53.7%









The present disclosure also includes Examples A through J above except “Compound 352” is replaced with “Compound 353”, “Compound 354”, “Compound 355”, “Compound 356”, “Compound 357”, “Compound 358”, “Compound 359”, “Compound 360”, “Compound 361”, “Compound 362”, “Compound 363”, “Compound 364”, “Compound 365”, “Compound 366”, “Compound 367”, “Compound 368”, “Compound 369”, “Compound 370”, “Compound 371”, “Compound 372”, “Compound 373”, “Compound 374”, “Compound 375”, “Compound 376”, “Compound 377”, “Compound 378”, “Compound 379”, “Compound 380”, “Compound 381”, “Compound 382”, “Compound 383”, “Compound 384”, “Compound 386”, “Compound 387”, “Compound 388”, “Compound 389”, “Compound 390”, “Compound 391”, “Compound 392”, “Compound 393”, “Compound 394”, “Compound 395”, “Compound 396”, “Compound 397”, “Compound 398”, “Compound 399”, “Compound 400”, “Compound 401”, “Compound 402”, “Compound 403”, “Compound 404”, “Compound 405”, “Compound 406”, “Compound 407”, “Compound 408”, “Compound 409”, “Compound 410”, “Compound 411”, “Compound 412”, “Compound 413”, “Compound 414”, “Compound 415”, “Compound 416”, “Compound 417”, “Compound 418”, “Compound 419”, “Compound 420”, “Compound 421”, “Compound 422”, “Compound 423”, “Compound 424”, “Compound 425”, “Compound 426”, “Compound 427”, “Compound 428”, “Compound 429”, “Compound 430”, “Compound 431”, “Compound 432”, “Compound 433”, “Compound 434”, “Compound 435”, “Compound 436”, “Compound 437”, “Compound 438”, “Compound 439”, “Compound 440”, “Compound 441”, “Compound 442”, “Compound 443”, “Compound 444”, “Compound 445”, “Compound 446”, “Compound 447”, “Compound 448”, “Compound 449”, “Compound 450”, “Compound 451”, “Compound 452”, “Compound 453”, “Compound 454”, “Compound 455”, “Compound 456”, “Compound 457”, “Compound 460”, “Compound 461”, “Compound 462”, “Compound 463”, “Compound 464”, “Compound 465”, “Compound 466”, “Compound 467”, “Compound 468”, “Compound 469”, “Compound 470”, “Compound 471”, “Compound 472”, “Compound 473”, “Compound 474”, “Compound 475”, “Compound 476”, “Compound 477”, “Compound 478”, “Compound 479”, “Compound 480”, “Compound 481”, “Compound 482”, “Compound 483”, “Compound 484”, “Compound 485”, “Compound 486”, “Compound 487”, “Compound 488”, “Compound 489”, “Compound 490”, “Compound 491”, “Compound 492”, “Compound 493”, “Compound 494”, “Compound 495”, “Compound 496”, “Compound 497”, “Compound 498”, “Compound 499”, “Compound 500”, “Compound 501”, “Compound 502”, “Compound 503”, “Compound 504”, “Compound 505”, “Compound 506”, “Compound 507”, “Compound 508”, “Compound 509”, “Compound 510”, “Compound 511”, “Compound 512”, “Compound 513”, “Compound 514”, “Compound 515”, “Compound 516”, “Compound 517”, “Compound 518”, “Compound 519”, “Compound 520”, “Compound 521”, “Compound 522”, “Compound 523”, “Compound 524”, “Compound 525”, “Compound 526”, “Compound 527”, “Compound 528”, “Compound 529”, “Compound 530”, “Compound 531”, “Compound 532”, “Compound 533”, “Compound 534”, “Compound 535”, “Compound 536”, “Compound 537”, “Compound 538”, “Compound 539”, “Compound 540”, “Compound 541”, “Compound 544”, “Compound 545”, “Compound 546”, “Compound 547”, “Compound 549”, “Compound 550”, “Compound 551”, “Compound 552”, “Compound 553”, “Compound 554”, “Compound 555”, “Compound 556”, “Compound 557”, “Compound 558”, “Compound 559”, “Compound 560”, “Compound 561”, “Compound 562”, “Compound 563”, “Compound 564”, “Compound 565”, “Compound 566”, “Compound 567”, “Compound 568”, “Compound 569”, “Compound 570”, “Compound 571”, “Compound 572”, “Compound 573”, “Compound 574”, “Compound 575”, “Compound 576”, “Compound 577”, “Compound 578”, “Compound 579”, “Compound 580”, “Compound 581”, “Compound 582”, “Compound 583”, “Compound 584”, “Compound 585”, “Compound 586”, “Compound 587”, “Compound 588”, “Compound 589”, “Compound 590”, “Compound 591”, “Compound 592”, “Compound 593”, “Compound 594”, “Compound 595”, “Compound 596”, “Compound 597”, “Compound 598”, “Compound 599”, “Compound 600”, “Compound 601”, “Compound 602”, “Compound 605”, “Compound 606”, “Compound 607”, “Compound 608”, “Compound 609”, “Compound 610”, “Compound 611”, “Compound 612”, “Compound 613”, “Compound 614”, “Compound 616”, “Compound 617”, “Compound 618”, “Compound 619”, “Compound 620”, “Compound 621”, “Compound 622”, “Compound 623”, “Compound 624”, “Compound 625”, “Compound 630”, “Compound 631”, “Compound 632”, “Compound 633”, “Compound 634”, “Compound 635”, “Compound 636”, “Compound 637”, “Compound 638”, “Compound 639”, “Compound 640”, “Compound 641”, “Compound 642”, “Compound 643”, “Compound 644”, “Compound 645”, “Compound 646”, “Compound 647”, “Compound 648”, “Compound 649”, “Compound 650”, “Compound 651”, “Compound 652”, “Compound 653”, “Compound 654”, “Compound 655”, “Compound 656”, “Compound 657”, “Compound 658”, “Compound 659”, “Compound 660”, “Compound 661”, “Compound 662”, “Compound 663”, “Compound 664”, “Compound 665”, “Compound 666”, “Compound 667”, “Compound 668”, “Compound 674”, “Compound 675”, “Compound 676”, “Compound 677”, “Compound 678”, “Compound 679”, “Compound 680”, “Compound 681”, “Compound 682”, “Compound 683”, “Compound 684”, “Compound 685”, “Compound 686”, “Compound 687”, “Compound 688”, “Compound 689”, “Compound 690”, “Compound 691”, “Compound 692”, “Compound 693”, “Compound 694”, “Compound 695”, “Compound 696”, “Compound 697”, “Compound 698”, “Compound 699”, “Compound 700”, “Compound 701”, “Compound 702”, “Compound 703”, “Compound 704”, “Compound 705”, “Compound 706”, “Compound 711”, “Compound 712”, “Compound 713”, “Compound 714”, “Compound 715”, “Compound 716”, “Compound 717”, “Compound 718”, “Compound 719”, “Compound 720”, “Compound 721”, “Compound 722”, “Compound 723”, “Compound 724”, “Compound 725”, “Compound 726”, “Compound 727”, “Compound 728”, “Compound 729”, “Compound 730”, “Compound 731”, “Compound 732”, “Compound 733”, “Compound 734”, “Compound 735”, “Compound 736”, “Compound 737”, “Compound 738”, “Compound 739”, “Compound 740”, “Compound 741”, “Compound 742”, “Compound 743”, “Compound 744”, “Compound 745”, “Compound 746”, “Compound 747”, “Compound 748”, “Compound 749”, “Compound 750”, “Compound 751”, “Compound 752”, “Compound 753”, “Compound 754”, “Compound 755”, “Compound 756”, “Compound 757”, “Compound 758”, “Compound 759”, “Compound 760”, “Compound 761”, “Compound 762”, “Compound 763”, “Compound 764”, “Compound 765”, “Compound 766”, “Compound 767”, “Compound 768”, “Compound 769”, “Compound 770”, “Compound 771”, “Compound 772”, “Compound 773”, “Compound 774”, “Compound 775”, “Compound 776”, “Compound 777”, “Compound 778”, “Compound 779”, “Compound 780”, “Compound 781”, “Compound 782”, “Compound 783”, “Compound 784”, “Compound 785”, “Compound 786”, “Compound 787”, “Compound 788”, “Compound 789”, “Compound 790”, “Compound 791”, “Compound 792”, “Compound 793”, “Compound 794”, “Compound 795”, “Compound 796”, “Compound 797”, “Compound 798”, “Compound 799”, “Compound 800”, “Compound 801”, “Compound 802”, “Compound 803”, “Compound 804”, “Compound 805”, “Compound 806”, “Compound 807”, “Compound 808”, “Compound 809”, “Compound 810”, “Compound 811”, “Compound 812”, “Compound 813”, “Compound 814”, “Compound 815”, “Compound 816”, “Compound 817”, “Compound 818”, “Compound 819”, “Compound 820”, “Compound 821”, “Compound 822”, “Compound 823”, “Compound 824”, “Compound 825”, “Compound 826”, “Compound 827”, “Compound 828”, “Compound 829”, “Compound 830”, “Compound 831”, “Compound 832”, “Compound 833”, “Compound 834”, “Compound 835”, “Compound 836”, “Compound 837”, “Compound 838”, “Compound 839”, “Compound 840”, “Compound 841”, “Compound 842”, “Compound 843”, “Compound 844”, “Compound 845”, “Compound 846”, “Compound 847”, “Compound 848”, “Compound 849”, “Compound 850”, “Compound 851”, “Compound 852”, “Compound 853”, “Compound 854”, “Compound 855”, “Compound 856”, “Compound 857”, “Compound 858”, “Compound 859”, “Compound 860”, “Compound 861”, “Compound 862”, “Compound 863”, “Compound 864”, “Compound 865”, “Compound 866”, “Compound 867”, “Compound 868”, “Compound 869”, “Compound 870”, “Compound 871”, “Compound 872”, “Compound 873”, “Compound 874”, “Compound 875”, “Compound 876”, “Compound 877”, “Compound 878”, “Compound 879”, “Compound 880”, “Compound 881”, “Compound 882”, “Compound 883”, “Compound 884”, “Compound 885”, “Compound 886”, “Compound 887”, “Compound 888”, “Compound 889”, “Compound 890”, “Compound 891”, “Compound 892”, “Compound 893”, “Compound 894”, “Compound 895”, “Compound 896”, “Compound 897”, “Compound 898”, “Compound 899”, “Compound 900”, “Compound 901”, “Compound 902”, “Compound 903”, “Compound 904”, “Compound 905”, “Compound 906”, “Compound 907”, “Compound 908”, “Compound 909”, “Compound 910”, “Compound 911”, “Compound 912”, “Compound 913”, “Compound 914”, “Compound 915”, “Compound 916”, “Compound 917”, “Compound 918”, “Compound 919”, “Compound 920”, “Compound 921”, “Compound 922”, “Compound 923”, “Compound 924”, “Compound 925”, “Compound 926”, “Compound 927”, “Compound 928”, “Compound 929”, “Compound 930”, “Compound 931”, “Compound 932”, “Compound 933”, “Compound 934”, “Compound 935”, “Compound 936”, “Compound 937”, “Compound 938”, “Compound 939”, “Compound 940”, “Compound 941”, “Compound 942”, “Compound 943”, “Compound 944”, “Compound 945”, “Compound 946”, “Compound 947”, “Compound 948”, “Compound 949”, “Compound 950”, “Compound 951”, “Compound 952”, “Compound 953”, “Compound 954”, “Compound 955”, “Compound 956”, “Compound 957”, “Compound 958”, “Compound 959”, “Compound 960”, “Compound 961”, “Compound 962”, “Compound 963”, “Compound 964”, “Compound 965”, “Compound 966”, “Compound 967”, “Compound 968”, “Compound 969”, “Compound 970”, “Compound 971”, “Compound 972”, “Compound 973”, “Compound 974”, “Compound 975”, “Compound 976”, “Compound 977”, “Compound 978”, “Compound 979”, “Compound 980”, “Compound 981”, “Compound 982”, “Compound 983”, “Compound 984”, “Compound 985”, “Compound 986”, “Compound 987”, “Compound 988”, “Compound 989”, “Compound 990”, “Compound 991”, “Compound 992”, “Compound 993”, “Compound 994”, “Compound 995”, “Compound 996”, “Compound 997”, “Compound 998”, “Compound 999”, “Compound 1000”, “Compound 1001”, “Compound 1002”, “Compound 1003”, “Compound 1004”, “Compound 1005”, “Compound 1006”, “Compound 1007”, “Compound 1008”, “Compound 1009”, “Compound 1010”, “Compound 1011”, “Compound 1012”, “Compound 1013”, “Compound 1014”, “Compound 1015”, “Compound 1016”, “Compound 1017”, “Compound 1018”, “Compound 1019”, “Compound 1020”, “Compound 1021”, “Compound 1022”, “Compound 1023”, “Compound 1024”, “Compound 1025”, “Compound 1026”, “Compound 1027”, “Compound 1028”, “Compound 1029”, “Compound 1030”, “Compound 1031”, “Compound 1032”, “Compound 1033”, “Compound 1034”, “Compound 1035”, “Compound 1036”, “Compound 1037”, “Compound 1038”, “Compound 1039”, “Compound 1040”, “Compound 1041”, “Compound 1042”, “Compound 1043”, “Compound 1044”, “Compound 1045”, “Compound 1046”, “Compound 1047”, “Compound 1048”, “Compound 1049”, “Compound 1050”, “Compound 1051”, “Compound 1052”, “Compound 1053”, “Compound 1054”, “Compound 1055”, “Compound 1056”, “Compound 1057”, “Compound 1058”, “Compound 1059”, “Compound 1060”, “Compound 1061”, “Compound 1062”, “Compound 1063”, “Compound 1064”, “Compound 1065”, “Compound 1066”, “Compound 1067”, “Compound 1068”, “Compound 1069”, “Compound 1070”, “Compound 1071”, “Compound 1072”, “Compound 1073”, “Compound 1074”, “Compound 1075”, “Compound 1076”, “Compound 1077”, “Compound 1078”, “Compound 1079”, “Compound 1080”, “Compound 1081”, “Compound 1082”, “Compound 1083”, “Compound 1084”, “Compound 1085”, “Compound 1086”, “Compound 1087”, “Compound 1088”, “Compound 1089”, “Compound 1090”, “Compound 1091”, “Compound 1092”, “Compound 1093”, “Compound 1094”, “Compound 1095”, “Compound 1096”, “Compound 1097”, “Compound 1098”, “Compound 1099”, “Compound 1100”, “Compound 1101”, “Compound 1102”, “Compound 1103”, “Compound 1104”, “Compound 1105”, “Compound 1106”, “Compound 1107”, “Compound 1108”, “Compound 1109”, “Compound 1110”, “Compound 1111”, “Compound 1112”, “Compound 1113”, “Compound 1114”, “Compound 1115”, “Compound 1116”, “Compound 1117”, “Compound 1118”, “Compound 1119”, “Compound 1120”, “Compound 1121”, “Compound 1122”, “Compound 1123”, “Compound 1124”, “Compound 1125”, “Compound 1126”, “Compound 1127”, “Compound 1128”, “Compound 1129”, “Compound 1130”, “Compound 1131”, “Compound 1132”, “Compound 1133”, “Compound 1134”, “Compound 1135”, “Compound 1136”, “Compound 1137”, “Compound 1138”, “Compound 1139”, “Compound 1140”, “Compound 1141”, “Compound 1142”, “Compound 1143”, “Compound 1144”, “Compound 1145”, “Compound 1146”, “Compound 1147”, “Compound 1148”, “Compound 1149”, “Compound 1150”, “Compound 1151”, “Compound 1152”, “Compound 1153”, “Compound 1154”, “Compound 1155”, “Compound 1156”, “Compound 1157”, “Compound 1158”, “Compound 1159”, “Compound 1160”, “Compound 1161”, “Compound 1162”, “Compound 1163”, “Compound 1164”, “Compound 1165”, “Compound 1166”, “Compound 1167”, “Compound 1168”, “Compound 1169”, “Compound 1170”, “Compound 1171”, “Compound 1172”, “Compound 1173”, “Compound 1174”, “Compound 1175”, “Compound 1176”, “Compound 1177”, “Compound 1178”, “Compound 1179”, “Compound 1180”, “Compound 1181”, “Compound 1182”, “Compound 1183”, “Compound 1184”, “Compound 1185”, “Compound 1186”, “Compound 1187”, “Compound 1188”, “Compound 1189”, “Compound 1190”, “Compound 1191”, “Compound 1192”, “Compound 1193”, “Compound 1194”, “Compound 1195”, “Compound 1196”, “Compound 1197”, “Compound 1198”, “Compound 1199”, “Compound 1200”, “Compound 1201”, “Compound 1202”, “Compound 1203”, “Compound 1204”, “Compound 1205”, “Compound 1206”, “Compound 1207”, “Compound 1208”, “Compound 1209”, “Compound 1210”, “Compound 1211”, “Compound 1212”, “Compound 1213”, “Compound 1214”, “Compound 1215”, “Compound 1216”, “Compound 1217”, “Compound 1218”, “Compound 1219”, “Compound 1220”, “Compound 1221”, “Compound 1222”, “Compound 1223”, “Compound 1224”, “Compound 1225”, “Compound 1226”, “Compound 1227”, “Compound 1228”, “Compound 1229”, “Compound 1230”, “Compound 1231”, “Compound 1232”, “Compound 1233”, “Compound 1234”, “Compound 1235”, “Compound 1236”, “Compound 1237”, “Compound 1238”, “Compound 1239”, “Compound 1240”, “Compound 1241”, “Compound 1242”, “Compound 1243”, “Compound 1244”, “Compound 1245”, “Compound 1246”, “Compound 1247”, “Compound 1248”, “Compound 1249”, “Compound 1250”, “Compound 1251”, “Compound 1252”, “Compound 1253”, “Compound 1254”, “Compound 1255”, “Compound 1256”, “Compound 1257”, “Compound 1258”, “Compound 1259”, “Compound 1260”, “Compound 1261”, “Compound 1262”, “Compound 1263”, “Compound 1264”, “Compound 1265”, “Compound 1266”, “Compound 1267”, “Compound 1268”, “Compound 1269”, “Compound 1270”, “Compound 1271”, “Compound 1272”, “Compound 1273”, “Compound 1274”, “Compound 1275”, “Compound 1276”, “Compound 1277”, “Compound 1278”, “Compound 1279”, “Compound 1280”, “Compound 1281”, “Compound 1282”, “Compound 1283”, “Compound 1284”, “Compound 1285”, “Compound 1286”, “Compound 1287”, “Compound 1288”, “Compound 1289”, “Compound 1290”, “Compound 1291”, “Compound 1292”, “Compound 1293”, “Compound 1294”, “Compound 1295”, “Compound 1296”, “Compound 1297”, “Compound 1298”, “Compound 1299”, “Compound 1300”, “Compound 1301”, “Compound 1302”, “Compound 1303”, “Compound 1304”, “Compound 1305”, “Compound 1306”, “Compound 1307”, “Compound 1308”, “Compound 1309”, “Compound 1310”, “Compound 1311”, “Compound 1312”, “Compound 1313”, “Compound 1314”, “Compound 1315”, “Compound 1316”, “Compound 1317”, “Compound 1318”, “Compound 1319”, “Compound 1320”, “Compound 1321”, “Compound 1322”, “Compound 1323”, “Compound 1324”, “Compound 1325”, “Compound 1326”, “Compound 1327”, “Compound 1328”, “Compound 1329”, “Compound 1330”, “Compound 1331”, “Compound 1332”, “Compound 1333”, “Compound 1334”, “Compound 1335”, “Compound 1336”, “Compound 1337”, “Compound 1338”, “Compound 1339”, “Compound 1340”, “Compound 1341”, “Compound 1342”, “Compound 1343”, “Compound 1344”, “Compound 1345”, “Compound 1346”, “Compound 1347”, “Compound 1348”, “Compound 1349”, “Compound 1350”, “Compound 1351”, “Compound 1352”, “Compound 1353”, “Compound 1354”, “Compound 1355”, “Compound 1356”, “Compound 1357”, “Compound 1358”, “Compound 1359”, “Compound 1360”, “Compound 1361”, “Compound 1362”, “Compound 1363”, “Compound 1364”, “Compound 1365”, “Compound 1366”, “Compound 1367”, “Compound 1368”, “Compound 1369”, “Compound 1370”, “Compound 1371”, “Compound 1372”, “Compound 1373”, “Compound 1374”, “Compound 1375”, “Compound 1376”, “Compound 1377”, “Compound 1378”, “Compound 1379”, “Compound 1380”, “Compound 1381”, “Compound 1382”, “Compound 1383”, “Compound 1384”, “Compound 1385”, “Compound 1386”, “Compound 1387”, “Compound 1388”, “Compound 1389”, “Compound 1390”, “Compound 1391”, “Compound 1392”, “Compound 1393”, “Compound 1394”, “Compound 1395”, “Compound 1396”, “Compound 1397”, “Compound 1398”, “Compound 1399”, “Compound 1400”, “Compound”, “Compound”, “Compound 1401”, “Compound”, “Compound”, “Compound 1402”, “Compound”, “Compound”, “Compound 1403”, “Compound 1404”, “Compound 1405”, “Compound 1406”, “Compound 1407”, “Compound 1408”, “Compound 1409”, “Compound 1410”, “Compound 1411”, “Compound 1412”, “Compound 1413”, “Compound 1414”, “Compound 1415”, “Compound 1416”, “Compound 1417”, “Compound 1418”, “Compound 1419”, “Compound 1420”, “Compound 1421”, “Compound 1422”, “Compound 1423”, “Compound 1424”, “Compound 1425”, “Compound 1426”, “Compound 1427”, “Compound 1428”, “Compound 1429”, “Compound 1430”, “Compound 1431”, “Compound 1432”, “Compound 1433”, “Compound 1434”, “Compound 1435”, “Compound 1436”, “Compound 1437”, “Compound 1438”, “Compound 1439”, “Compound 1440”, “Compound 1441”, “Compound 1442”, “Compound 1443”, “Compound 1444”, “Compound 145”, “Compound 1446”, “Compound 1447”, “Compound 1448”, “Compound 1449”, “Compound 1450”, “Compound 1451”, “Compound 1452”, “Compound 1453”, “Compound 1454”, “Compound 1455”, “Compound 1456”, “Compound 1457”, “Compound 1458”, “Compound 1459”, “Compound 1460”, “Compound 1461”, “Compound 1462”, “Compound 1463”, “Compound 1464”, “Compound 1465”, “Compound 1466”, “Compound 1467”, “Compound 1468”, “Compound 1469”, “Compound 1470”, “Compound 1471”, “Compound 1472”, “Compound 1473”, “Compound 1474”, “Compound 1475”, “Compound 1476”, “Compound 1477”, “Compound 1478”, “Compound 1479”, “Compound 1480”, “Compound 1481”, “Compound 1482”, “Compound 1483”, “Compound 1484”, “Compound 1485”, “Compound 1486”, “Compound 1487”, “Compound 1488”, “Compound 1489”, “Compound 1490”, “Compound 1491”, “Compound 1492”, “Compound 1493”, “Compound 1494”, “Compound 1495”, “Compound 1496”, “Compound 1497”, “Compound 1498”, “Compound 1499”, “Compound 1500”, “Compound 1501”, “Compound 1502”, “Compound 1503”, “Compound 1504”, “Compound 1505”, “Compound 1506”, “Compound 1507”, “Compound 1508”, “Compound 1509”, “Compound 1510”, “Compound 1511”, “Compound 1512”, “Compound 1513”, “Compound 1514”, “Compound 1515”, “Compound 1516”, “Compound 1517”, “Compound 1518”, “Compound 1519”, “Compound 1520”, “Compound 1521”, “Compound 1522”, “Compound 1523”, “Compound 1524”, “Compound 1525”, “Compound 1526”, “Compound 1527”, “Compound 1528”, “Compound 1529”, “Compound 1530”, “Compound 1531”, “Compound 1532”, “Compound 1533”, “Compound 1534”, “Compound 1535”, “Compound 1536”, “Compound 1537”, “Compound 1538”, “Compound 1539”, “Compound 1540”, “Compound 1541”, “Compound 1542”, “Compound 1543”, “Compound 1544”, “Compound 1545”, “Compound 1546”, “Compound 1547”, “Compound 1548”, “Compound 1549”, “Compound 1550”, “Compound 1551”, “Compound 1552”, “Compound 1553”, “Compound 1554”, “Compound 1555”, “Compound 1556”, “Compound 1557”, “Compound 1558”, “Compound 1559”, “Compound 1560”, “Compound 1561”, “Compound 1562”, “Compound 1563”, “Compound 1564”, “Compound 1565”, “Compound 1566”, “Compound 1567”, “Compound 1568”, “Compound 1569”, “Compound 1570”, “Compound 1571”, “Compound 1572”, “Compound 1573”, “Compound 1574”, “Compound 1575”, “Compound 1576”, “Compound 1577”, “Compound 1578”, “Compound 1579”, “Compound 1580”, “Compound 1581”, “Compound 1582”, “Compound 1583”, “Compound 1584”, “Compound 1585”, “Compound 1586”, “Compound 1587”, “Compound 1588”, “Compound 1589”, “Compound 1590”, “Compound 1591”, “Compound 1592”, “Compound 1593”, “Compound 1594”, “Compound 1595”, “Compound 1596”, “Compound 1597”, “Compound 1598”, “Compound 1599”, “Compound 1600”, “Compound 1601”, “Compound 1602”, “Compound 1603”, “Compound 1604”, “Compound 1605”, “Compound 1606”, “Compound 1607”, “Compound 1608”, “Compound 1609”, “Compound 1610”, “Compound 1611”, “Compound 1612”, “Compound 1613”, “Compound 1614”, “Compound 1615”, “Compound 1616”, “Compound 1617”, “Compound 1618”, “Compound 1619”, “Compound 1620”, “Compound 1621”, “Compound 1622”, “Compound 1623”, “Compound 1624”, “Compound 1625”, “Compound 1626”, “Compound 1627”, “Compound 1628”, “Compound 1629”, “Compound 1630”, “Compound 1631”, “Compound 1632”, “Compound 1633”, “Compound 1634”, “Compound 1635”, “Compound 1636”, “Compound 1637”, “Compound 1638”, “Compound 1639”, “Compound 1640”, “Compound 1641”, “Compound 1642”, “Compound 1643”, “Compound 1644”, “Compound 1645”, “Compound 1646”, “Compound 1647”, “Compound 1648”, “Compound 1649”, “Compound 1650”, “Compound 1651”, “Compound 1652”, “Compound 1653”, “Compound 1654”, “Compound 1655”, “Compound 1656”, “Compound 1657”, “Compound 1658”, “Compound 1659”, “Compound 1660”, “Compound 1661”, “Compound 1662”, “Compound 1663”, “Compound 1664”, “Compound 1665”, “Compound 1666”, “Compound 1667”, “Compound 1668”, “Compound 1669”, “Compound 1670”, “Compound 1671”, “Compound 1672”, “Compound 1673”, “Compound 1674”, “Compound 1675”, “Compound 1676”, “Compound 1677”, “Compound 1678”, “Compound 1679”, “Compound 1680”, “Compound 1681”, “Compound 1682”, “Compound 1683”, “Compound 1684”, “Compound 1685”, “Compound 1686”, “Compound 1687”, “Compound 1688”, “Compound 1689”, “Compound 1690”, “Compound 1691”, “Compound 1692”, “Compound 1693”, “Compound 1694”, “Compound 1695”, “Compound 1696”, “Compound 1697”, “Compound 1698”, “Compound 1699”, “Compound 1700”, “Compound 1701”, “Compound 1702”, “Compound 1703”, “Compound 1704”, “Compound 1705”, “Compound 1706”, “Compound 1707”, “Compound 1708”, “Compound 1709”, “Compound 1710”, “Compound 1711”, “Compound 1712”, “Compound 1713”, “Compound 1714”, “Compound 1715”, “Compound 1716”, “Compound 1717”, “Compound 1718”, “Compound 1719”, “Compound 1720”, “Compound 1721”, “Compound 1722”, “Compound 1723”, “Compound 1724”, “Compound 1725”, “Compound 1726”, “Compound 1727”, “Compound 1728”, “Compound 1729”, “Compound 1730”, “Compound 1731”, “Compound 1732”, “Compound 1733”, “Compound 1734”, “Compound 1735”, “Compound 1736”, “Compound 1737”, “Compound 1738”, “Compound 1739”, “Compound 1740”, “Compound 1741”, “Compound 1742”, “Compound 1743”, “Compound 1744”, “Compound 1745”, “Compound 1746”, “Compound 1747”, “Compound 1748”, “Compound 1749”, “Compound 1750”, “Compound 1751”, “Compound 1752”, “Compound 1753”, “Compound 1754”, “Compound 1755”, “Compound 1756”, “Compound 1757”, “Compound 1758”, “Compound 1759”, “Compound 1760”, “Compound 1761”, “Compound 1762”, “Compound 1763”, “Compound 1764”, “Compound 1765”, “Compound 1766”, “Compound 1767”, “Compound 1768”, “Compound 1769”, “Compound 1770”, “Compound 1771”, “Compound 1772”, “Compound 1773”, “Compound 1774”, “Compound 1775”, “Compound 1776”, “Compound 1777”, “Compound 1778”, “Compound 1779”, “Compound 1780”, “Compound 1781”, “Compound 1782”, “Compound 1783”, “Compound 1784”, “Compound 1785”, “Compound 1786”, “Compound 1787”, “Compound 1788”, “Compound 1789”, “Compound 1790”, “Compound 1791”, “Compound 1792”, “Compound 1793”, “Compound 1794”, “Compound 1795”, “Compound 1796”, “Compound 1797”, “Compound 1798”, “Compound 1799”, “Compound 1800”, “Compound 1801”, “Compound 1802”, “Compound 1803”, “Compound 1804”, “Compound 1805”, “Compound 1806”, “Compound 1807”, “Compound 1808”, “Compound 1809”, “Compound 1810”, “Compound 1811”, “Compound 1812”, “Compound 1813”, “Compound 1814”, “Compound 1815”, “Compound 1816”, “Compound 1817”, “Compound 1818”, “Compound 1819”, “Compound 1820”, “Compound 1821”, “Compound 1822”, “Compound 1823”, “Compound 1824”, “Compound 1825”, “Compound 1826”, “Compound 1827”, “Compound 1828”, “Compound 1829”, “Compound 1830”, “Compound 1831”, “Compound 1832”, “Compound 1833”, “Compound 1834”, “Compound 1835”, “Compound 1836”, “Compound 1837”, “Compound 1838”, “Compound 1839”, “Compound 1840”, “Compound 1841”, “Compound 1842”, “Compound 1843”, “Compound 1844”, “Compound 1845”, “Compound 1846”, “Compound 1847”, “Compound 1848”, “Compound 1849”, “Compound 1850”, “Compound 1851”, “Compound 1852”, “Compound 1853”, “Compound 1854”, “Compound 1855”, “Compound 1856”, “Compound 1857”, “Compound 1858”, “Compound 1859”, “Compound 1860”, “Compound 1861”, “Compound 1862”, “Compound 1863”, “Compound 1864”, “Compound 1865”, “Compound 1866”, “Compound 1867”, “Compound 1868”, “Compound 1869”, “Compound 1870”, “Compound 1871”, “Compound 1872”, “Compound 1873” or “Compound 1874” above.


Test results indicate that many compounds of the present disclosure are highly active preemergent and/or postemergent herbicides and/or plant growth regulants. Many compounds of this disclosure generally show highest activity for early postemergence weed control (i.e. applied soon after weed seedlings emerge from the soil) and preemergence weed control (i.e. applied before weed seedlings emerge from the soil). Many of them have utility for broad-spectrum pre- and/or postemergence weed control in areas where complete control of all vegetation is desired such as around fuel storage tanks, industrial storage areas, parking lots, drive-in theaters, air fields, river banks, irrigation and other waterways, around billboards and highway and railroad structures. Many of the compounds of this disclosure, by virtue of selective metabolism in crops versus weeds, or by selective activity at the locus of physiological inhibition in crops and weeds, or by selective placement on or within the environment of a mixture of crops and weeds, are useful for the selective control of grass and broadleaf weeds within a crop/weed mixture. One skilled in the art will recognize that a desired combination of these selectivity factors within a compound or group of compounds can readily be determined by performing routine biological and/or biochemical assays. Compounds of this disclosure may show tolerance to important agronomic crops including, but is not limited to, alfalfa, barley, cotton, wheat, rape, sugar beets, corn (maize), sorghum, soybeans, rice, oats, peanuts, vegetables, tomato, potato, perennial plantation crops including coffee, cocoa, oil palm, rubber, sugarcane, citrus, grapes, fruit trees, nut trees, banana, plantain, pineapple, hops, tea and forests such as eucalyptus and conifers (e.g., loblolly pine), and turf species (e.g., Kentucky bluegrass, St. Augustine grass, Kentucky fescue and Bermuda grass). Many compounds of this disclosure can be used in crops genetically transformed or bred to incorporate resistance to herbicides, express proteins toxic to invertebrate pests (such as Bacillus thuringiensis toxin), and/or express other useful traits. Those skilled in the art will appreciate that not all compounds are equally effective against all weeds. Alternatively, the subject compounds are useful to modify plant growth.


As many compounds of this disclosure have (both preemergent and postemergent herbicidal) activity, to control undesired vegetation by killing or injuring the vegetation or reducing its growth, the compounds can be usefully applied by a variety of methods involving contacting a herbicidally effective amount of a compound of this disclosure, or a composition comprising said compound and at least one of a surfactant, a solid diluent or a liquid diluent, to the foliage or other part of the undesired vegetation or to the environment of the undesired vegetation such as the soil or water in which the undesired vegetation is growing or which surrounds the seed or other propagule of the undesired vegetation.


A herbicidally effective amount of the compounds of this disclosure is determined by a number of factors. These factors include: formulation selected, method of application, amount and type of vegetation present, growing conditions, etc. In general, a herbicidally effective amount of compounds of this disclosure is from about 0.005 to about 20 kg/ha. In some embodiments, the range is from about 0.01 to about 1 kg/ha. One skilled in the art can easily determine the herbicidally effective amount necessary for the desired level of weed control.


Compounds of the disclosure are useful in treating all plants and plant parts. Plant varieties and cultivars can be obtained by conventional propagation and breeding methods or by genetic engineering methods. Genetically modified plants (transgenic plants) are those in which a heterologous gene (transgene) has been stably integrated into the plant's genome. A transgene that is defined by its particular location in the plant genome is called a transformation or transgenic event.


Genetically modified plant cultivars which can be treated according to this disclosure include those that are resistant against one or more biotic stresses (pests such as nematodes, insects, mites, fungi, etc.) or abiotic stresses (drought, cold temperature, soil salinity, etc.), or that contain other desirable characteristics. Plants can be genetically modified to exhibit traits of, for example, herbicide tolerance, insect-resistance, modified oil profiles or drought tolerance. Useful genetically modified plants containing single gene transformation events or combinations of transformation events are listed in Table 3. Additional information for the genetic modifications listed in Table 3 can be obtained from publicly available databases maintained, for example, by the U.S. Department of Agriculture.


The following abbreviations, T1 through T37, are used in Table 3 for traits. A “-” means the entry is not available.















Trait
Description








T1
Glyphosate tolerance



T2
High lauric acid oil



T3
Glufosinate tolerance



T4
Phytate breakdown



T5
Oxynil tolerance



T6
Disease resistance



T7
Insect resistance



T9
Modified flower color



T11
ALS Herbicide Tol.



T12
Dicamba Tolerance



T13
Anti-allergy



T14
Salt tolerance



T15
Cold tolerance



T16
Imidazolinone herb. tol.



T17
Modified alpha-amylase



T18
Pollination control



T19
2,4-D tolerance



T20
Increased lysine



T21
Drought tolerance



T22
Delayed ripening/senescence



T23
Modified product quality



T24
High cellulose



T25
Modified starch/carbohydrate



T26
Insect & disease resist.



T27
High tryptophan



T28
Erect leaves semidwarf



T29
Semidwarf



T30
Low iron tolerance



T31
Modified oil/fatty acid



T32
HPPD tolerance



T33
High oil



T34
Aryloxyalkanoate tol.



T35
Mesotrione tolerance



T36
Reduced nicotine



T37
Modified product




















TABLE 3





Crop
Event Name
Event Code
Trait(s)
Gene(s)







Alfalfa
J101
MON-00101-8
T1
cp4 epsps (aroA:CP4)


Alfalfa
J163
MON-ØØ163-7
T1
cp4 epsps (aroA:CP4)


Canola*
23-18-17 (Event 18)
CGN-89465-2
T2
te


Canola*
23-198 (Event 23)
CGN-89465-2
T2
te


Canola*
61061
DP-Ø61Ø61-7
T1
gat4621


Canola*
73496
DP-Ø73496-4
T1
gat4621


Canola*
GT200 (RT200)
MON-89249-2
T1
cp4 epsps (aroA:CP4); goxv247


Canola*
GT73 (RT73)
MON-ØØØ73-7
T1
cp4 epsps (aroA:CP4); goxv247


Canola*
HCN10 (Topas 19/2)

T3
bar


Canola*
HCN28 (T45)
ACS-BNØØ8-2
T3
pat (syn)


Canola*
HCN92 (Topas 19/2)
ACS-BNØØ7-1
T3
bar


Canola*
MON88302
MON-883Ø2-9
T1
cp4 epsps (aroA:CP4)


Canola*
MPS961

T4
phyA


Canola*
MPS962

T4
phyA


Canola*
MPS963

T4
phyA


Canola*
MPS964

T4
phyA


Canola*
MPS965

T4
phyA


Canola*
MS1 (B91-4)
ACS-BNØØ4-7
T3
bar


Canola*
MS8
ACS-BNØØ5-8
T3
bar


Canola*
OXY-235
ACS-BNØ11-5
T5
bxn


Canola*
PHY14

T3
bar


Canola*
PHY23

T3
bar


Canola*
PHY35

T3
bar


Canola*
PHY36

T3
bar


Canola*
RF1 (B93-101)
ACS-BNØØ1-4
T3
bar


Canola*
RF2 (B94-2)
ACS-BNØØ2-5
T3
bar


Canola*
RF3
ACS-BNØØ3-6
T3
bar


Bean
EMBRAPA 5.1
EMB-PV051-1
T6
ac1 (sense and antisense)


Brinjal #
EE-1

T7
cry1Ac


Cotton
19-51a
DD-Ø1951A-7
T11
S4-HrA


Cotton
281-24-236
DAS-24236-5
T3, T7
pat (syn); cry1F


Cotton
3006-210-23
DAS-21Ø23-5
T3, T7
pat (syn); cry1Ac


Cotton
31707

T5, T7
bxn; cry1Ac


Cotton
31803

T5, T7
bxn; cry1Ac


Cotton
31807

T5, T7
bxn; cry1Ac


Cotton
31808

T5, T7
bxn; cry1Ac


Cotton
42317

T5, T7
bxn; cry1Ac


Cotton
BNLA-601

T7
cry1Ac


Cotton
BXN10211
BXN10211-9
T5
bxn; cry1Ac


Cotton
BXN10215
BXN10215-4
T5
bxn; cry1Ac


Cotton
BXN10222
BXN10222-2
T5
bxn; cry1Ac


Cotton
BXN10224
BXN10224-4
T5
bxn; cry1Ac


Cotton
COT102
SYN-IRB102-7
T7
vip3A(a)


Cotton
COT67B
SYN-IR67B-1
T7
cry1Ab


Cotton
COT202

T7
vip3A


Cotton
Event 1

T7
cry1Ac


Cotton
GMF Cry1A
GTL-GMF311-7
T7
cry1Ab-Ac


Cotton
GHB119
BCS-GH005-8
T7
cry2Ae


Cotton
GHB614
BCS-GH002-5
T1
2mepsps


Cotton
GK12

T7
cry1Ab-Ac


Cotton
LLCotton25
ACS-GH001-3
T3
bar


Cotton
MLS 9124

T7
cry1C


Cotton
MON1076
MON-89924-2
T7
cry1Ac


Cotton
MON1445
MON-01445-2
T1
cp4 epsps (aroA:CP4)


Cotton
MON15985
MON-15985-7
T7
cry1Ac; cry2Ab2


Cotton
MON1698
MON-89383-1
T7
cp4 epsps (aroA:CP4)


Cotton
MON531
MON-00531-6
T7
cry1Ac


Cotton
MON757
MON-00757-7
T7
cry1Ac


Cotton
MON88913
MON-88913-8
T1
cp4 epsps (aroA:CP4)


Cotton
Nqwe Chi 6 Bt

T7



Cotton
SKG321

T7
cry1A; CpTI


Cotton
T303-3
BCS-GH003-6
T3, T7
cry1Ab; bar


Cotton
T304-40
BCS-GH004-7
T3, T7
cry1Ab; bar


Cotton
CE43-67B

T7
cry1Ab


Cotton
CE46-02A

T7
cry1Ab


Cotton
CE44-69D

T7
cry1Ab


Cotton
1143-14A

T7
cry1Ab


Cotton
1143-51B

T7
cry1Ab


Cotton
T342-142

T7
cry1Ab


Cotton
PV-GHGT07 (1445)

T1
cp4 epsps (aroA:CP4)


Cotton
EE-GH3

T1
mepsps


Cotton
EE-GH5

T7
cry1Ab


Cotton
MON88701
MON-88701-3
T3, T12
Modified dmo; bar


Cotton
OsCr11

T13
Modified Cry j


Flax
FP967
CDC-FL001-2
T11
als


Lentil
RH44

T16
als


Maize
3272
SYN-E3272-5
T17
amy797E


Maize
5307
SYN-05307-1
T7
ecry3.1Ab


Maize
59122
DAS-59122-7
T3, T7
cry34Ab1; cry35Ab1; pat


Maize
676
PH-000676-7
T3, T18
pat; dam


Maize
678
PH-000678-9
T3, T18
pat; dam


Maize
680
PH-000680-2
T3, T18
pat; dam


Maize
98140
DP-098140-6
T1, T11
gat4621; zm-hra


Maize
Bt10

T3, T7
cry1Ab; pat


Maize
Bt176 (176)
SYN-EV176-9
T3, T7
cry1Ab; bar


Maize
BVLA430101

T4
phyA2


Maize
CBH-351
ACS-ZM004-3
T3, T7
cry9C; bar


Maize
DAS40278-9
DAS40278-9
T19
aad-1


Maize
DBT418
DKB-89614-9
T3, T7
cry1Ac; pinII; bar


Maize
DLL25 (B16)
DKB-89790-5
T3
bar


Maize
GA21
MON-00021-9
T1
mepsps


Maize
GG25

T1
mepsps


Maize
GJ11

T1
mepsps


Maize
Fl117

T1
mepsps


Maize
GAT-ZM1

T3
pat


Maize
LY038
REN-00038-3
T20
cordapA


Maize
MIR 162
SYN-IR162-4
T7
vip3Aa20


Maize
MIR604
SYN-IR604-5
T7
mcry3A


Maize
MON801 (MON80100)
MON801
T1, T7
cry1Ab; cp4 epsps (aroA:CP4);






goxv247


Maize
MON802
MON-80200-7
T1, T7
cry1Ab; cp4 epsps (aroA:CP4);






goxv247


Maize
MON809
PH-MON-809-2
T1, T7
cry1Ab; cp4 epsps (aroA:CP4);






goxv247


Maize
MON810
MON-00810-6
T1, T7
cry1Ab; cp4 epsps (aroA:CP4);






goxv247


Maize
MON832

T1
cp4 epsps (aroA:CP4); goxv247


Maize
MON863
MON-00863-5
T7
cry3Bb1


Maize
MON87427
MON-87427-7
T1
cp4 epsps (aroA:CP4)


Maize
MON87460
MON-87460-4
T21
cspB


Maize
MON88017
MON-88017-3
T1, T7
cry3Bb1; cp4 epsps (aroA:CP4)


Maize
MON89034
MON-89034-3
T7
cry2Ab2; cry1A.105


Maize
MS3
ACS-ZM001-9
T3, T18
bar; barnase


Maize
MS6
ACS-ZM005-4
T3, T18
bar; barnase


Maize
NK603
MON-00603-6
T1
cp4 epsps (aroA:CP4)


Maize
T14
ACS-ZM002-1
T3
pat (syn)


Maize
T25
ACS-ZM003-2
T3
pat (syn)


Maize
TC1507
DAS-01507-1
T3, T7
cry1Fa2; pat


Maize
TC6275
DAS-06275-8
T3, T7
mocry1F; bar


Maize
VIP1034

T3, T7
vip3A; pat


Maize
43A47
DP-043A47-3
T3, T7
cry1F; cry34Ab1; cry35Ab1; pat


Maize
40416
DP-040416-8
T3, T7
cry1F; cry34Ab1; cry35Ab1; pat


Maize
32316
DP-032316-8
T3, T7
cry1F; cry34Ab1; cry35Ab1; pat


Maize
4114
DP-004114-3
T3, T7
cry1F; cry34Ab1; cry35Ab1; pat


Melon
Melon A

T22
sam-k


Melon
Melon B

T22
sam-k


Papaya
55-1
CUH-CP551-8
T6
prsv cp


Papaya
63-1
CUH-CP631-7
T6
prsv cp


Papaya
Huanong No. 1

T6
prsv rep


Papaya
X17-2
UFL-X17CP-6
T6
prsv cp


Plum
C-5
ARS-PLMC5-6
T6
ppv cp


Canola**
ZSR500

T1
cp4 epsps (aroA:CP4); goxv247


Canola**
ZSR502

T1
cp4 epsps (aroA:CP4); goxv247


Canola**
ZSR503

T1
cp4 epsps (aroA:CP4); goxv247


Rice
7Crp#242-95-7

T13
7crp


Rice
7Crp#10

T13
7crp


Rice
GM Shanyou 63

T7
cry1Ab; cry1Ac


Rice
Huahui-1/TT51-1

T7
cry1Ab; cry1Ac


Rice
LLRICE06
ACS-OS001-4
T3
bar


Rice
LLRICE601
BCS-OS003-7
T3
bar


Rice
LLRICE62
ACS-OS002-5
T3
bar


Rice
Tarom molaii + cry1Ab

T7
cry1Ab (truncated)


Rice
GAT-OS2

T3
bar


Rice
GAT-OS3

T3
bar


Rice
PE-7

T7
Cry1Ac


Rice
7Crp#10

T13
7crp


Rice
KPD627-8

T27
OASA1D


Rice
KPD722-4

T27
OASA1D


Rice
KA317

T27
OASA1D


Rice
HW5

T27
OASA1D


Rice
HW1

T27
OASA1D


Rice
B-4-1-18

T28
Δ OsBRI1


Rice
G-3-3-22

T29
OSGA2ox1


Rice
AD77

T6
DEF


Rice
AD51

T6
DEF


Rice
AD48

T6
DEF


Rice
AD41

T6
DEF


Rice
13pNasNa800725atAprt1

T30
HvNAS1; HvNAAT-A; APRT


Rice
13pAprt1

T30
APRT


Rice
gHvNAS1-gHvNAAT-1

T30
HvNAS1; HvNAAT-A; HvNAAT-B


Rice
gHvIDS3-1

T30
HvIDSS


Rice
gHvNAAT1

T30
HvNAAT-A; HvNAAT-B


Rice
gHvNAS1-1

T30
HvNAS1


Rice
NIA-OS006-4

T6
WRKY45


Rice
NIA-OS005-3

T6
WRKY45


Rice
NIA-OS004-2

T6
WRKY45


Rice
NIA-OS003-1

T6
WRKY45


Rice
NIA-OS002-9

T6
WRKY45


Rice
NIA-OS001-8

T6
WRKY45


Rice
OsCr11

T13
Modified Cry j


Rice
17053

T1
cp4 epsps (aroA:CP4)


Rice
17314

T1
cp4 epsps (aroA:CP4)


Rose
WKS82/130-4-1
IFD-52401-4
T9
5AT; bp40 (f3′5′h)


Rose
WKS92/130-9-1
IFD-52901-9
T9
5AT; bp40 (f3′5′h)


Soybean
260-05 (G94-1, G94-19,

T9
gm-fad2-1 (silencing locus)



G168)





Soybean
A2704-12
ACS-GM005-3
T3
pat


Soybean
A2704-21
ACS-GM004-2
T3
pat


Soybean
A5547-127
ACS-GM006-4
T3
pat


Soybean
A5547-35
ACS-GM008-6
T3
pat


Soybean
CV127
BPS-CV127-9
T16
csr1-2


Soybean
DAS68416-4
DAS68416-4
T3
pat


Soybean
DP305423
DP-305423-1
T11, T31
gm-fad2-1 (silencing locus); gm-hra


Soybean
DP356043
DP-356043-5
T1, T31
gm-fad2-1 (silencing locus);






gat4601


Soybean
FG72
MST-FG072-3
T32, T1
2mepsps; hppdPF W336


Soybean
GTS 40-3-2 (40-3-2)
MON-04032-6
T1
cp4 epsps (aroA:CP4)


Soybean
GU262
ACS-GM003-1
T3
pat


Soybean
MON87701
MON-87701-2
T7
cry1Ac


Soybean
MON87705
MON-87705-6
T1, T31
fatb1-A (sense & antisense); fad2-






1A (sense & antisense); cp4 epsps






(aroA:CP4)


Soybean
MON87708
MON-87708-9
T1, T12
dmo; cp4 epsps (aroA:CP4)


Soybean
MON87769
MON-87769-7
T1, T31
Pj.D6D; Nc.Fad3; cp4 epsps






(aroA:CP4)


Soybean
MON89788
MON-89788-1
T1
cp4 epsps (aroA:CP4)


Soybean
W62
ACS-GM002-9
T3
bar


Soybean
W98
ACS-GM001-8
T3
bar


Soybean
MON87754
MON-87754-1
T33
dgat2A


Soybean
DAS21606
DAS-21606
T34, T3
Modified aad-12; pat


Soybean
DAS44406
DAS-44406-6
T1, T3, T34
Modified aad-12; 2mepsps; pat


Soybean
SYHT04R
SYN-0004R-8
T35
Modified avhppd


Soybean
9582.814.19.1

T3, T7
cry1Ac, cry1F, PAT


Squash
CZW3
SEM-ØCZW3-2
T6
cmv cp, zymv cp, wmv cp


Squash
ZW20
SEM-0ZW20-7
T6
zymv cp, wmv cp


Sugar Beet
GTSB77 (T9100152)
SY-GTSB77-8
T1
cp4 epsps (aroA:CP4); goxv247


Sugar Beet
H7-1
KM-000H71-4
T1
cp4 epsps (aroA:CP4)


Sugar Beet
T120-7
ACS-BV001-3
T3
pat


Sugar Beet
T227-1

T1
cp4 epsps (aroA:CP4)


Sugarcane
NXI-1T

T21
EcbetA


Sunflower
X81359

T16
als


Pepper
PK-SP01

T6
cmv cp


Tobacco
C/F/93/08-02

T5
bxn


Tobacco
Vector 21-41

T36
NtQPT1 (antisense)


Sunflower
X81359

T16
als


Wheat
MON71800
MON-718ØØ-3
T1
cp4 epsps (aroA:CP4)





*Argentine (Brassica napus),


**Polish (B. rapa),


# Eggplant






Treatment of genetically modified plants with compounds of this disclosure may result in super-additive or synergistic effects. For example, reduction in application rates, broadening of the activity spectrum, increased tolerance to biotic/abiotic stresses or enhanced storage stability may be greater than expected from just simple additive effects of the application of compounds of this disclosure on genetically modified plants.


Compounds of this disclosure can also be mixed with one or more other biologically active compounds or agents including herbicides, herbicide safeners, fungicides, insecticides, nematocides, bactericides, acaricides, growth regulators such as insect molting inhibitors and rooting stimulants, chemosterilants, semiochemicals, repellents, attractants, pheromones, feeding stimulants, plant nutrients, other biologically active compounds or entomopathogenic bacteria, virus or fungi to form a multi-component pesticide giving an even broader spectrum of agricultural protection. Mixtures of compounds of this disclosure with other herbicides can broaden the spectrum of activity against additional weed species, and suppress the proliferation of any resistant biotypes. Thus the present disclosure also pertains to a composition comprising a compound of Formula 1 (in a herbicidally effective amount) and at least one additional biologically active compound or agent (in a biologically effective amount) and can further comprise at least one of a surfactant, a solid diluent or a liquid diluent. The other biologically active compounds or agents can be formulated in compositions comprising at least one of a surfactant, solid or liquid diluent. For mixtures of the present disclosure, one or more other biologically active compounds or agents can be formulated together with a compound of Formula 1, to form a premix, or one or more other biologically active compounds or agents can be formulated separately from the compound of Formula 1, and the formulations combined together before application (e.g., in a spray tank) or, alternatively, applied in succession.


A mixture of one or more of the following herbicides with a compound of this disclosure may be particularly useful for weed control: acetochlor, acifluorfen and its sodium salt, aclonifen, acrolein (2-propenal), alachlor, alloxydim, ametryn, amicarbazone, amidosulfuron, aminocyclopyrachlor and its esters (e.g., methyl, ethyl) and salts (e.g., sodium, potassium), aminopyralid, amitrole, ammonium sulfamate, anilofos, asulam, atrazine, azimsulfuron, beflubutamid, benazolin, benazolin-ethyl, bencarbazone, benfluralin, benfuresate, bensulfuron-methyl, bensulide, bentazone, benzobicyclon, benzofenap, bicyclopyrone, bifenox, bilanafos, bispyribac and its sodium salt, bromacil, bromobutide, bromofenoxim, bromoxynil, bromoxynil octanoate, butachlor, butafenacil, butamifos, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone-ethyl, catechin, chlomethoxyfen, chloramben, chlorbromuron, chlorflurenol-methyl, chloridazon, chlorimuron-ethyl, chlorotoluron, chlorpropham, chlorsulfuron, chlorthal-dimethyl, chlorthiamid, cinidon-ethyl, cinmethylin, cinosulfuron, clacyfos, clefoxydim, clethodim, cyclopyrimorate, clodinafop-propargyl, clomazone, clomeprop, clopyralid, clopyralid-olamine, cloransulam-methyl, cumyluron, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop-butyl, 2,4-D and its butotyl, butyl, isoctyl and isopropyl esters and its dimethylammonium, diolamine and trolamine salts, daimuron, dalapon, dalapon-sodium, dazomet, 2,4-DB and its dimethylammonium, potassium and sodium salts, desmedipham, desmetryn, dicamba and its diglycolammonium, dimethylammonium, potassium and sodium salts, dichlobenil, dichlorprop, diclofop-methyl, diclosulam, difenzoquat metilsulfate, diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimethipin, dimethylarsinic acid and its sodium salt, dinitramine, dinoterb, diphenamid, diquat dibromide, dithiopyr, diuron, DNOC, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron-methyl, ethiozin, ethofumesate, ethoxyfen, ethoxysulfuron, etobenzanid, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenquinotrione, fentrazamide, fenuron, fenuron-TCA, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop-butyl, fluazifop-P-butyl, fluazolate, flucarbazone, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac-pentyl, flumioxazin, fluometuron, fluoroglycofen-ethyl, flupoxam, flupyrsulfuron-methyl and its sodium salt, flurenol, flurenol-butyl, fluridone, flurochloridone, fluroxypyr, flurtamone, fluthiacet-methyl, fomesafen, foramsulfuron, fosamine-ammonium, glufosinate, glufosinate-ammonium, glufosinate-P, glyphosate and its salts such as ammonium, isopropylammonium, potassium, sodium (including sesquisodium) and trimesium (alternatively named sulfosate), halauxifen, halauxifen-methyl, halosulfuron-methyl, haloxyfop-etotyl, haloxyfop-methyl, hexazinone, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr-ammonium, imazosulfuron, indanofan, indaziflam, iofensulfuron, iodosulfuron-methyl, ioxynil, ioxynil octanoate, ioxynil-sodium, ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutole, isoxachlortole, lactofen, lenacil, linuron, maleic hydrazide, MCPA and its salts (e.g., MCPA-dimethylammonium, MCPA-potassium and MCPA-sodium, esters (e.g., MCPA-2-ethylhexyl, MCPA-butotyl) and thioesters (e.g., MCPA-thioethyl), MCPB and its salts (e.g., MCPB-sodium) and esters (e.g., MCPB-ethyl), mecoprop, mecoprop-P, mefenacet, mefluidide, mesosulfuron-methyl, mesotrione, metam-sodium, metamifop, metamitron, metazachlor, metazosulfuron, methabenzthiazuron, methylarsonic acid and its calcium, monoammonium, monosodium and disodium salts, methyldymron, metobenzuron, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron-methyl, molinate, monolinuron, naproanilide, napropamide, napropamide-M, naptalam, neburon, nicosulfuron, norflurazon, orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat dichloride, pebulate, pelargonic acid, pendimethalin, penoxsulam, pentanochlor, pentoxazone, perfluidone, pethoxamid, pethoxyamid, phenmedipham, picloram, picloram-potassium, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen-ethyl, pyrasulfotole, pyrazogyl, pyrazolynate, pyrazoxyfen, pyrazosulfuron-ethyl, pyribenzoxim, pyributicarb, pyridate, pyriftalid, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop-ethyl, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, saflufenacil, sethoxydim, siduron, simazine, simetryn, sulcotrione, sulfentrazone, sulfometuron-methyl, sulfosulfuron, 2,3,6-TBA, TCA, TCA-sodium, tebutam, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbumeton, terbuthylazine, terbutryn, thenylchlor, thiazopyr, thiencarbazone, thifensulfuron-methyl, thiobencarb, tiafenacil, tiocarbazil, topramezone, tralkoxydim, tri-allate, triafamone, triasulfuron, triaziflam, tribenuron-methyl, triclopyr, triclopyr-butotyl, triclopyr-triethylammonium, tridiphane, trietazine, trifloxysulfuron, trifluralin, triflusulfuron-methyl, tritosulfuron, vernolate, 3-(2-chloro-3,6-difluorophenyl)-4-hydroxy-1-methyl-,5-naphthyridin-2(1H)-one, 5-chloro-3-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-1-(4-methoxyphenyl)-2(1H)-quinoxalinone, 2-chloro-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)-3-pyridinecarboxamide, 7-(3,5-dichloro-4-pyridinyl)-5-(2,2-difluoroethyl)-8-hydroxypyrido[2,3-b]pyrazin-6(5H)-one), 4-(2,6-diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone), 5-[[(2,6-difluorophenyl)methoxy]methyl]-4,5-dihydro-5-methyl-3-(3-methyl-2-thienyl)isoxazole (previously methioxolin), 3-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propyn-1-yl)-2H-1,4-benzoxazin-6-yl]dihydro-1,5-dimethyl-6-thioxo-1,3,5-triazine-2,4(1H,3H)-dione, 4-(4-fluorophenyl)-6-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-methyl-1,2,4-triazine-3,5(2H,4H)-dione, methyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylate, 2-methyl-3-(methylsulfonyl)-N-(1-methyl-H-tetrazol-5-yl)-4-(trifluoromethyl)benzamide, and 2-methyl-N-(4-methyl-1,2,5-oxadiazol-3-yl)-3-(methylsulfinyl)-4-(trifluoromethyl)benzamide. Other herbicides also include bioherbicides such as Alternaria destruens Simmons, Colletotrichum gloeosporiodes (Penz.) Penz. & Sacc., Drechsiera monoceras (MTB-951), Myrothecium verrucaria (Albertini & Schweinitz) Ditmar: Fries, Phytophthora palmivora (Butl.) Butl. and Puccinia thlaspeos Schub.


Compounds of this disclosure can also be used in combination with plant growth regulators such as aviglycine, N-(phenylmethyl)-1H-purin-6-amine, epocholeone, gibberellic acid, gibberellin A4 and A7, harpin protein, mepiquat chloride, prohexadione calcium, prohydrojasmon, sodium nitrophenolate and trinexapac-methyl, and plant growth modifying organisms such as Bacillus cereus strain BP01.


General references for agricultural protectants (i.e. herbicides, herbicide safeners, insecticides, fungicides, nematocides, acaricides and biological agents) include The Pesticide Manual, 13th Edition, C. D. S. Tomlin, Ed., British Crop Protection Council, Farnham, Surrey, U. K., 2003 and The BioPesticide Manual, 2nd Edition, L. G. Copping, Ed., British Crop Protection Council, Farnham, Surrey, U. K., 2001.


For embodiments where one or more of these various mixing partners are used, the weight ratio of these various mixing partners (in total) to the compound of Formula 1 is typically between about 1:3000 and about 3000:1. Of note are weight ratios between about 1:300 and about 300:1 (for example ratios between about 1:30 and about 30:1). One skilled in the art can easily determine through simple experimentation the biologically effective amounts of active ingredients necessary for the desired spectrum of biological activity. It will be evident that including these additional components may expand the spectrum of weeds controlled beyond the spectrum controlled by the compound of Formula 1 alone.


In certain instances, combinations of a compound of this disclosure with other biologically active (particularly herbicidal) compounds or agents (i.e. active ingredients) can result in a greater-than-additive (i.e. synergistic) effect on weeds and/or a less-than-additive effect (i.e. safening) on crops or other desirable plants. Reducing the quantity of active ingredients released in the environment while ensuring effective pest control is always desirable. Ability to use greater amounts of active ingredients to provide more effective weed control without excessive crop injury is also desirable. When synergism of herbicidal active ingredients occurs on weeds at application rates giving agronomically satisfactory levels of weed control, such combinations can be advantageous for reducing crop production cost and decreasing environmental load. When safening of herbicidal active ingredients occurs on crops, such combinations can be advantageous for increasing crop protection by reducing weed competition.


Of note is a combination of a compound of this disclosure with at least one other herbicidal active ingredient. Of particular note is such a combination where the other herbicidal active ingredient has different site of action from the compound of this disclosure. In certain instances, a combination with at least one other herbicidal active ingredient having a similar spectrum of control but a different site of action will be particularly advantageous for resistance management. Thus, a composition of the present disclosure can further comprise (in a herbicidally effective amount) at least one additional herbicidal active ingredient having a similar spectrum of control but a different site of action.


Compounds of this disclosure can also be used in combination with herbicide safeners such as allidochlor, benoxacor, cloquintocet-mexyl, cumyluron, cyometrinil, cyprosulfonamide, daimuron, dichlormid, dicyclonon, dietholate, dimepiperate, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen-ethyl, mefenpyr-diethyl, mephenate, methoxyphenone, naphthalic anhydride (1,8-naphthalic anhydride), oxabetrinil, N-(aminocarbonyl)-2-methylbenzenesulfonamide, N-(aminocarbonyl)-2-fluorobenzenesulfonamide, 1-bromo-4-[(chloromethyl)sulfonyl]benzene (BCS), 4-(dichloroacetyl)-1-oxa-4-azospiro[4.5]decane (MON 4660), 2-(dichloromethyl)-2-methyl-1,3-dioxolane (MG 191), ethyl 1,6-dihydro-1-(2-methoxyphenyl)-6-oxo-2-phenyl-5-pyrimidinecarboxylate, 2-hydroxy-N,N-dimethyl-6-(trifluoromethyl)pyridine-3-carboxamide, 3-oxo-1-cyclohexen-1-yl 1-(3,4-dimethylphenyl)-1,6-dihydro-6-oxo-2-phenyl-5-pyrimidinecarboxylate, 2,2-dichloro-1-(2,2,5-trimethyl-3-oxazolidinyl)-ethanone and 2-methoxy-N-[[4-[[(methylamino)carbonyl]amino]phenyl]sulfonyl]-benzamide (alternatively named N-(2-methoxybenzoyl)-4-[(methylaminocarbonyl)amino] benzenesulfonamide, CAS #129531-12-0) to increase safety to certain crops. Antidotally effective amounts of the herbicide safeners can be applied at the same time as a compound of this disclosure, or applied as seed treatments. Therefore an aspect of the present disclosure relates to a herbicidal mixture comprising a compound of this disclosure and an antidotally effective amount of a herbicide safener. Seed treatment is particularly useful for selective weed control, because it physically restricts antidoting to the crop plants. Therefore a particularly useful embodiment of the present disclosure is a method for selectively controlling the growth of undesired vegetation in a crop comprising contacting the locus of the crop with a herbicidally effective amount of a compound of this disclosure wherein seed from which the crop is grown is treated with an antidotally effective amount of safener. Antidotally effective amounts of safeners can be easily determined by one skilled in the art through simple experimentation.


Of note is a composition comprising a compound of this disclosure (in a herbicidally effective amount), at least one additional active ingredient selected from the group consisting of other herbicides and herbicide safeners (in an effective amount), and at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents.


In some embodiments, a mixture of a compound of this disclosure is used in combination with another herbicide for better control of undesired vegetation (e.g., lower use rate such as from synergism, broader spectrum of weeds controlled, or enhanced crop safety) or for preventing the development of resistant weeds. Table A1 lists particular combinations of Component (a) (i.e. a specific compound of the present disclosure) with another herbicideas Component (b) illustrative of the mixtures, compositions and methods of the present disclosure. Compound 17 in the Component (a) column is identified in Index Table A. The second column of Table A1 lists the specific Component (b) compound (e.g., “2,4-D” in the first line). The third, fourth and fifth columns of Table A1 lists ranges of weight ratios for rates at which the Component (a) compound is typically applied to afield-grown crop relative to Component (b) (i.e. (a):(b)). Thus, for example, the first line of Table A1 specifically discloses the combination of Component (a) (i.e. Compound 17 in Index Table A) with 2,4-D is typically applied in a weight ratio between 1:192-6:1. The remaining lines of Table A1 are to be construed similarly:













TABLE A1





Component (a)

Typical
More Typical
Most Typical


(Compound #)
Component (b)
Weight Ratio
Weight Ratio
Weight Ratio



















352
2,4-D
1:192-6:1
1:64-2:1
1:24-1:3


352
Acetochlor
1:768-2:1
1:256-1:2 
 1:96-1:11


352
Acifluorfen
 1:96-12:1
1:32-4:1
1:12-1:2


352
Aclonifen
1:857-2:1
1:285-1:3 
1:107-1:12


352
Alachlor
1:768-2:1
1:256-1:2 
 1:96-1:11


352
Ametryn
1:384-3:1
1:128-1:1 
1:48-1:6


352
Amicarbazone
1:192-6:1
1:64-2:1
1:24-1:3


352
Amidosulfuron
  1:6-168:1
 1:2-56:1
 1:1-11:1


352
Aminocyclopyrachlor
 1:48-24:1
1:16-8:1
 1:6-2:1


352
Aminopyralid
 1:20-56:1
 1:6-19:1
 1:2-4:1


352
Amitrole
1:768-2:1
1:256-1:2 
 1:96-1:11


352
Anilofos
 1:96-12:1
1:32-4:1
1:12-1:2


352
Asulam
1:960-2:1
1:320-1:3 
1:120-1:14


352
Atrazine
1:192-6:1
1:64-2:1
1:24-1:3


352
Azimsulfuron
  1:6-168:1
 1:2-56:1
 1:1-11:1


352
Beflubutamid
1:342-4:1
1:114-2:1 
1:42-1:5


352
Benfuresate
1:617-2:1
1:205-1:2 
1:77-1:9


352
Bensulfuron-methyl
 1:25-45:1
 1:8-15:1
 1:3-3:1


352
Bentazone
1:192-6:1
1:64-2:1
1:24-1:3


352
Benzobicyclon
 1:85-14:1
1:28-5:1
1:10-1:2


352
Benzofenap
1:257-5:1
1:85-2:1
1:32-1:4


352
Bicyclopyrone
 1:42-27:1
1:14-9:1
 1:5-2:1


352
Bifenox
1:257-5:1
1:85-2:1
1:32-1:4


352
Bispyribac-sodium
  1:10-112:1
 1:3-38:1
 1:1-7:1


352
Bromacil
1:384-3:1
1:128-1:1 
1:48-1:6


352
Bromobutide
1:384-3:1
1:128-1:1 
1:48-1:6


352
Bromoxynil
 1:96-12:1
1:32-4:1
1:12-1:2


352
Butachlor
1:768-2:1
1:256-1:2 
 1:96-1:11


352
Butafenacil
 1:42-27:1
1:14-9:1
 1:5-2:1


352
Butylate
1:1542-1:2 
1:514-1:5 
1:192-1:22


352
Cafenstrole
1:192-6:1
1:64-2:1
1:24-1:3


352
Carfentrazone-ethyl
1:128-9:1
1:42-3:1
1:16-1:2


352
Chlorimuron-ethyl
  1:8-135:1
 1:2-45:1
 1:1-9:1


352
Chlorotoluron
1:768-2:1
1:256-1:2 
 1:96-1:11


352
Chlorsulfuron
  1:6-168:1
 1:2-56:1
 1:1-11:1


352
Cinosulfuron
 1:17-68:1
 1:5-23:1
 1:2-5:1


352
Cinidon-ethyl
1:384-3:1
1:128-1:1 
1:48-1:6


352
Cinmethylin
 1:34-34:1
 1:11-12:1
 1:4-3:1


352
Clacyfos
 1:34-34:1
 1:11-12:1
 1:4-3:1


352
Clethodim
 1:48-24:1
1:16-8:1
 1:6-2:1


352
Clodinafop-propargyl
 1:20-56:1
 1:6-19:1
 1:2-4:1


352
Clomazone
1:384-3:1
1:128-1:1 
1:48-1:6


352
Clomeprop
1:171-7:1
1:57-3:1
1:21-1:3


352
Clopyralid
1:192-6:1
1:64-2:1
1:24-1:3


352
Cloransulam-methyl
 1:12-96:1
 1:4-32:1
 1:1-6:1


352
Cumyluron
1:384-3:1
1:128-1:1 
1:48-1:6


352
Cyanazine
1:384-3:1
1:128-1:1 
1:48-1:6


352
Cyclopyrimorate
 1:17-68:1
 1:5-23:1
 1:2-5:1


352
Cyclosulfamuron
 1:17-68:1
 1:5-23:1
 1:2-5:1


352
Cycloxydim
 1:96-12:1
1:32-4:1
1:12-1:2


352
Cyhalofop
 1:25-45:1
 1:8-15:1
 1:3-3:1


352
Daimuron
1:192-6:1
1:64-2:1
1:24-1:3


352
Desmedipham
1:322-4:1
1:107-2:1 
1:40-1:5


352
Dicamba
1:192-6:1
1:64-2:1
1:24-1:3


352
Dichlobenil
1:1371-1:2 
1:457-1:4 
1:171-1:20


352
Dichlorprop
1:925-2:1
1:308-1:3 
1:115-1:13


352
Diclofop-methyl
1:384-3:1
1:128-1:1 
1:48-1:6


352
Diclosulam
  1:10-112:1
 1:3-38:1
 1:1-7:1


352
Difenzoquat
1:288-4:1
1:96-2:1
1:36-1:4


352
Diflufenican
1:857-2:1
1:285-1:3 
1:107-1:12


352
Diflufenzopyr
 1:12-96:1
 1:4-32:1
 1:1-6:1


352
Dimethachlor
1:768-2:1
1:256-1:2 
 1:96-1:11


352
Dimethametryn
1:192-6:1
1:64-2:1
1:24-1:3


352
Dimethenamid-P
1:384-3:1
1:128-1:1 
1:48-1:6


352
Dithiopyr
1:192-6:1
1:64-2:1
1:24-1:3


352
Diuron
1:384-3:1
1:128-1:1 
1:48-1:6


352
EPTC
1:768-2:1
1:256-1:2 
 1:96-1:11


352
Esprocarb
1:1371-1:2 
1:457-1:4 
1:171-1:20


352
Ethalfluralin
1:384-3:1
1:128-1:1 
1:48-1:6


352
Ethametsulfuron-methyl
 1:17-68:1
 1:5-23:1
 1:2-5:1


352
Ethoxyfen
  1:8-135:1
 1:2-45:1
 1:1-9:1


352
Ethoxysulfuron
 1:20-56:1
 1:6-19:1
 1:2-4:1


352
Etobenzanid
1:257-5:1
1:85-2:1
1:32-1:4


352
Fenoxaprop-ethyl
 1:120-10:1
1:40-4:1
1:15-1:2


352
Fenoxasulfone
 1:85-14:1
1:28-5:1
1:10-1:2


352
Fenquinotrione
 1:17-68:1
 1:5-23:1
 1:2-5:1


352
Fentrazamide
 1:17-68:1
 1:5-23:1
 1:2-5:1


352
Flazasulfuron
 1:17-68:1
 1:5-23:1
 1:2-5:1


352
Florasulam
  1:2-420:1
  1:1-140:1
 2:1-27:1


352
Fluazifop-butyl
1:192-6:1
1:64-2:1
1:24-1:3


352
Flucarbazone
  1:8-135:1
 1:2-45:1
 1:1-9:1


352
Flucetosulfuron
  1:8-135:1
 1:2-45:1
 1:1-9:1


352
Flufenacet
1:257-5:1
1:85-2:1
1:32-1:4


352
Flumetsulam
 1:24-48:1
 1:8-16:1
 1:3-3:1


352
Flumiclorac-pentyl
  1:10-112:1
 1:3-38:1
 1:1-7:1


352
Flumioxazin
 1:25-45:1
 1:8-15:1
 1:3-3:1


352
Fluometuron
1:384-3:1
1:128-1:1 
1:48-1:6


352
Flupyrsulfuron-methyl
  1:3-336:1
  1:1-112:1
 2:1-21:1


352
Fluridone
1:384-3:1
1:128-1:1 
1:48-1:6


352
Fluroxypyr
 1:96-12:1
1:32-4:1
1:12-1:2


352
Flurtamone
1:857-2:1
1:285-1:3 
1:107-1:12


352
Fluthiacet-methyl
 1:48-42:1
 1:16-14:1
 1:3-3:1


352
Fomesafen
 1:96-12:1
1:32-4:1
1:12-1:2


352
Foramsulfuron
 1:13-84:1
 1:4-28:1
 1:1-6:1


352
Glufosinate
1:288-4:1
1:96-2:1
1:36-1:4


352
Glyphosate
1:288-4:1
1:96-2:1
1:36-1:4


352
Halauxifen
 1:20-56:1
 1:6-19:1
 1:2-4:1


352
Halauxifen-methyl
 1:20-56:1
 1:6-19:1
 1:2-4:1


352
Halosulfuron-methyl
 1:17-68:1
 1:5-23:1
 1:2-5:1


352
Haloxyfop-methyl
 1:34-34:1
 1:11-12:1
 1:4-3:1


352
Hexazinone
1:192-6:1
1:64-2:1
1:24-1:3


352
Imazamox
 1:13-84:1
 1:4-28:1
 1:1-6:1


352
Imazapic
 1:20-56:1
 1:6-19:1
 1:2-4:1


352
Imazapyr
 1:85-14:1
1:28-5:1
1:10-1:2


352
Imazaquin
 1:34-34:1
 1:11-12:1
 1:4-3:1


352
Imazethabenz-methyl
1:171-7:1
1:57-3:1
1:21-1:3


352
Imazethapyr
 1:24-48:1
 1:8-16:1
 1:3-3:1


352
Imazosulfuron
 1:27-42:1
 1:9-14:1
 1:3-3:1


352
Indanofan
1:342-4:1
1:114-2:1 
1:42-1:5


352
Indaziflam
 1:25-45:1
 1:8-15:1
 1:3-3:1


352
Iodosulfuron-methyl
  1:3-336:1
  1:1-112:1
 2:1-21:1


352
Ioxynil
1:192-6:1
1:64-2:1
1:24-1:3


352
Ipfencarbazone
 1:85-14:1
1:28-5:1
1:10-1:2


352
Isoproturon
1:384-3:1
1:128-1:1 
1:48-1:6


352
Isoxaben
1:288-4:1
1:96-2:1
1:36-1:4


352
Isoxaflutole
 1:60-20:1
1:20-7:1
 1:7-2:1


352
Lactofen
 1:42-27:1
1:14-9:1
 1:5-2:1


352
Lenacil
1:384-3:1
1:128-1:1 
1:48-1:6


352
Linuron
1:384-3:1
1:128-1:1 
1:48-1:6


352
MCPA
1:192-6:1
1:64-2:1
1:24-1:3


352
MCPB
1:288-4:1
1:96-2:1
1:36-1:4


352
Mecoprop
1:768-2:1
1:256-1:2 
 1:96-1:11


352
Mefenacet
1:384-3:1
1:128-1:1 
1:48-1:6


352
Mefluidide
1:192-6:1
1:64-2:1
1:24-1:3


352
Mesosulfuron-methyl
  1:5-224:1
 1:1-75:1
 1:1-14:1


352
Mesotrione
 1:42-27:1
1:14-9:1
 1:5-2:1


352
Metamifop
 1:42-27:1
1:14-9:1
 1:5-2:1


352
Metazachlor
1:384-3:1
1:128-1:1 
1:48-1:6


352
Metazosulfuron
 1:25-45:1
 1:8-15:1
 1:3-3:1


352
Methabenzthiazuron
1:768-2:1
1:256-1:2 
 1:96-1:11


352
Metolachlor
1:768-2:1
1:256-1:2 
 1:96-1:11


352
Metosulam
  1:8-135:1
 1:2-45:1
 1:1-9:1


352
Metribuzin
1:192-6:1
1:64-2:1
1:24-1:3


352
Metsulfuron-methyl
  1:2-560:1
  1:1-187:1
 3:1-35:1


352
Molinate
1:1028-2:1 
1:342-1:3 
1:128-1:15


352
Napropamide
1:384-3:1
1:128-1:1 
1:48-1:6


352
Napropamide-M
1:192-6:1
1:64-2:1
1:24-1:3


352
Naptalam
1:192-6:1
1:64-2:1
1:24-1:3


352
Nicosulfuron
 1:12-96:1
 1:4-32:1
 1:1-6:1


352
Norflurazon
1:1152-1:1 
1:384-1:3 
1:144-1:16


352
Orbencarb
1:1371-1:2 
1:457-1:4 
1:171-1:20


352
Orthosulfamuron
 1:20-56:1
 1:6-19:1
 1:2-4:1


352
Oryzalin
1:514-3:1
1:171-1:2 
1:64-1:8


352
Oxadiargyl
1:384-3:1
1:128-1:1 
1:48-1:6


352
Oxadiazon
1:548-3:1
1:182-1:2 
1:68-1:8


352
Oxasulfuron
 1:27-42:1
 1:9-14:1
 1:3-3:1


352
Oxaziclomefone
 1:42-27:1
1:14-9:1
 1:5-2:1


352
Oxyfluorfen
1:384-3:1
1:128-1:1 
1:48-1:6


352
Paraquat
1:192-6:1
1:64-2:1
1:24-1:3


352
Pendimethalin
1:384-3:1
1:128-1:1 
1:48-1:6


352
Penoxsulam
  1:10-112:1
 1:3-38:1
 1:1-7:1


352
Penthoxamid
1:384-3:1
1:128-1:1 
1:48-1:6


352
Pentoxazone
 1:102-12:1
1:34-4:1
1:12-1:2


352
Phenmedipham
 1:102-12:1
1:34-4:1
1:12-1:2


352
Picloram
 1:96-12:1
1:32-4:1
1:12-1:2


352
Picolinafen
 1:34-34:1
 1:11-12:1
 1:4-3:1


352
Pinoxaden
 1:25-45:1
 1:8-15:1
 1:3-3:1


352
Pretilachlor
1:192-6:1
1:64-2:1
1:24-1:3


352
Primisulfuron-methyl
  1:8-135:1
 1:2-45:1
 1:1-9:1


352
Prodiamine
1:384-3:1
1:128-1:1 
1:48-1:6


352
Profoxydim
 1:42-27:1
1:14-9:1
 1:5-2:1


352
Prometryn
1:384-3:1
1:128-1:1 
1:48-1:6


352
Propachlor
1:1152-1:1 
1:384-1:3 
1:144-1:16


352
Propanil
1:384-3:1
1:128-1:1 
1:48-1:6


352
Propaquizafop
 1:48-24:1
1:16-8:1
 1:6-2:1


352
Propoxycarbazone
 1:17-68:1
 1:5-23:1
 1:2-5:1


352
Propyrisulfuron
 1:17-68:1
 1:5-23:1
 1:2-5:1


352
Propyzamide
1:384-3:1
1:128-1:1 
1:48-1:6


352
Prosulfocarb
1:1200-1:2 
1:400-1:4 
1:150-1:17


352
Prosulfuron
  1:6-168:1
 1:2-56:1
 1:1-11:1


352
Pyraclonil
 1:42-27:1
1:14-9:1
 1:5-2:1


352
Pyraflufen-ethyl
  1:5-224:1
 1:1-75:1
 1:1-14:1


352
Pyrasulfotole
 1:13-84:1
 1:4-28:1
 1:1-6:1


352
Pyrazolynate
1:857-2:1
1:285-1:3 
1:107-1:12


352
Pyrazosulfuron-ethyl
  1:10-112:1
 1:3-38:1
 1:1-7:1


352
Pyrazoxyfen
  1:5-224:1
 1:1-75:1
 1:1-14:1


352
Pyribenzoxim
  1:10-112:1
 1:3-38:1
 1:1-7:1


352
Pyributicarb
1:384-3:1
1:128-1:1 
1:48-1:6


352
Pyridate
1:288-4:1
1:96-2:1
1:36-1:4


352
Pyriftalid
  1:10-112:1
 1:3-38:1
 1:1-7:1


352
Pyriminobac-methyl
 1:20-56:1
 1:6-19:1
 1:2-4:1


352
Pyrimisulfan
 1:17-68:1
 1:5-23:1
 1:2-5:1


352
Pyrithiobac
 1:24-48:1
 1:8-16:1
 1:3-3:1


352
Pyroxasulfone
 1:85-14:1
1:28-5:1
1:10-1:2


352
Pyroxsulam
  1:5-224:1
 1:1-75:1
 1:1-14:1


352
Quinclorac
1:192-6:1
1:64-2:1
1:24-1:3


352
Quizalofop-ethyl
 1:42-27:1
1:14-9:1
 1:5-2:1


352
Rimsulfuron
 1:13-84:1
 1:4-28:1
 1:1-6:1


352
Saflufenacil
 1:25-45:1
 1:8-15:1
 1:3-3:1


352
Sethoxydim
 1:96-12:1
1:32-4:1
1:12-1:2


352
Simazine
1:384-3:1
1:128-1:1 
1:48-1:6


352
Sulcotrione
 1:120-10:1
1:40-4:1
1:15-1:2


352
Sulfentrazone
1:147-8:1
1:49-3:1
1:18-1:3


352
Sulfometuron-methyl
 1:34-34:1
 1:11-12:1
 1:4-3:1


352
Sulfosulfuron
  1:8-135:1
 1:2-45:1
 1:1-9:1


352
Tebuthiuron
1:384-3:1
1:128-1:1 
1:48-1:6


352
Tefuryltrione
 1:42-27:1
1:14-9:1
 1:5-2:1


352
Tembotrione
 1:31-37:1
 1:10-13:1
 1:3-3:1


352
Tepraloxydim
 1:25-45:1
 1:8-15:1
 1:3-3:1


352
Terbacil
1:288-4:1
1:96-2:1
1:36-1:4


352
Terbuthylazine
1:857-2:1
1:285-1:3 
1:107-1:12


352
Terbutryn
1:192-6:1
1:64-2:1
1:24-1:3


352
Thenylchlor
 1:85-14:1
1:28-5:1
1:10-1:2


352
Thiazopyr
1:384-3:1
1:128-1:1 
1:48-1:6


352
Thiencarbazone
  1:3-336:1
  1:1-112:1
 2:1-21:1


352
Thifensulfuron-methyl
  1:5-224:1
 1:1-75:1
 1:1-14:1


352
Tiafenacil
 1:17-68:1
 1:5-23:1
 1:2-5:1


352
Thiobencarb
1:768-2:1
1:256-1:2 
 1:96-1:11


352
Topramezone
  1:6-168:1
 1:2-56:1
 1:1-11:1


352
Tralkoxydim
 1:68-17:1
1:22-6:1
 1:8-2:1


352
Triallate
1:768-2:1
1:256-1:2 
 1:96-1:11


352
Triasulfuron
  1:5-224:1
 1:1-75:1
 1:1-14:1


352
Triaziflam
1:171-7:1
1:57-3:1
1:21-1:3


352
Tribenuron-methyl
  1:3-336:1
  1:1-112:1
 2:1-21:1


352
Triclopyr
1:192-6:1
1:64-2:1
1:24-1:3


352
Trifloxysulfuron
  1:2-420:1
  1:1-140:1
 2:1-27:1


352
Trifluralin
1:288-4:1
1:96-2:1
1:36-1:4


352
Triflusulfuron-methyl
 1:17-68:1
 1:5-23:1
 1:2-5:1


352
Tritosulfuron
 1:13-84:1
 1:4-28:1
 1:1-6:1


352
N-(2-methoxybenzoyl)-4-
 1:100-100:1
 1:50-50:1
 1:2-2:1



[(methylaminocarbonyl)ami-






no]benzenesulfonamide









Table A2 is constructed the same as Table A1 above except that entries below the “Component (a)” column heading are replaced with the respective “Component (a) Column Entry” shown below. Compound 353 in the Component (a) column is identified in Index Table A. Thus, for example, in Table A2 the entries below the “Component (a)” column heading all recite “Compound 353” (i.e. Compound 353 identified in Index Table A), and the first line below the column headings in Table A2 specifically discloses a mixture of Compound 353 with 2,4-D. Tables A3 et seq. are constructed similarly.















Table
Component (a)



No.
Column Entry








A2
Compound 353



A3
Compound 354



A4
Compound 355



A5
Compound 356



A6
Compound 357



A7
Compound 358



A8
Compound 359



A9
Compound 360



A10
Compound 361



A11
Compound 362



A12
Compound 363



A13
Compound 364



A14
Compound 365



A15
Compound 366



A16
Compound 367



A17
Compound 368



A18
Compound 369



A19
Compound 370



A20
Compound 371



A21
Compound 372



A22
Compound 373



A23
Compound 374



A24
Compound 375



A25
Compound 376



A26
Compound 377



A27
Compound 378



A28
Compound 379



A29
Compound 380



A30
Compound 381



A31
Compound 382



A32
Compound 383



A33
Compound 384



A35
Compound 386



A36
Compound 387



A37
Compound 388



A38
Compound 389



A39
Compound 390



A40
Compound 391



A41
Compound 392



A42
Compound 393



A43
Compound 394



A44
Compound 395



A45
Compound 396



A46
Compound 397



A47
Compound 398



A48
Compound 399



A49
Compound 400



A50
Compound 401



A51
Compound 402



A52
Compound 403



A53
Compound 404



A54
Compound 405



A55
Compound 406



A56
Compound 407



A57
Compound 408



A58
Compound 409



A59
Compound 410



A60
Compound 411



A61
Compound 412



A62
Compound 413



A63
Compound 414



A64
Compound 415



A65
Compound 416



A66
Compound 417



A67
Compound 418



A68
Compound 419



A69
Compound 420



A70
Compound 421



A71
Compound 422



A72
Compound 423



A73
Compound 424



A74
Compound 425



A75
Compound 426



A76
Compound 427



A77
Compound 428



A78
Compound 429



A79
Compound 430



A80
Compound 431



A81
Compound 432



A82
Compound 433



A83
Compound 434



A84
Compound 435



A85
Compound 436



A86
Compound 437



A87
Compound 438



A88
Compound 439



A89
Compound 440



A90
Compound 441



A91
Compound 442



A92
Compound 443



A93
Compound 444



A94
Compound 445



A95
Compound 446



A96
Compound 447



A97
Compound 448



A98
Compound 449



A99
Compound 450



A100
Compound 451



A101
Compound 452



A102
Compound 453



A103
Compound 454



A104
Compound 455



A105
Compound 456



A106
Compound 457



A107
Compound 460



A108
Compound 461



A109
Compound 462



A110
Compound 463



A111
Compound 464



A112
Compound 465



A113
Compound 466



A114
Compound 467



A115
Compound 468



A116
Compound 469



A117
Compound 470



A118
Compound 471



A119
Compound 472



A120
Compound 473



A121
Compound 474



A122
Compound 475



A123
Compound 476



A124
Compound 477



A125
Compound 478



A126
Compound 479



A127
Compound 480



A128
Compound 481



A129
Compound 482



A130
Compound 483



A131
Compound 484



A132
Compound 485



A133
Compound 486



A134
Compound 487



A135
Compound 488



A136
Compound 489



A137
Compound 490



A138
Compound 491



A139
Compound 492



A140
Compound 493



A141
Compound 494



A142
Compound 495



A143
Compound 496



A144
Compound 497



A145
Compound 498



A146
Compound 499



A147
Compound 500



A148
Compound 501



A149
Compound 502



A150
Compound 503



A151
Compound 504



A152
Compound 505



A153
Compound 506



A154
Compound 507



A155
Compound 508



A156
Compound 509



A157
Compound 510



A158
Compound 511



A159
Compound 512



A160
Compound 513



A161
Compound 514



A162
Compound 515



A163
Compound 516



A164
Compound 517



A165
Compound 518



A166
Compound 519



A167
Compound 520



A168
Compound 521



A169
Compound 522



A170
Compound 523



A171
Compound 524



A172
Compound 525



A173
Compound 526



A174
Compound 527



A175
Compound 528



A176
Compound 529



A177
Compound 530



A178
Compound 531



A179
Compound 532



A180
Compound 533



A181
Compound 534



A182
Compound 535



A183
Compound 536



A184
Compound 537



A185
Compound 538



A186
Compound 539



A187
Compound 540



A188
Compound 541



A192
Compound 545



A193
Compound 546



A194
Compound 547



A196
Compound 549



A197
Compound 550



A198
Compound 551



A199
Compound 552



A200
Compound 553



A201
Compound 554



A202
Compound 555



A203
Compound 556



A204
Compound 557



A205
Compound 558



A206
Compound 559



A207
Compound 560



A208
Compound 561



A209
Compound 562



A210
Compound 563



A211
Compound 564



A212
Compound 565



A213
Compound 566



A214
Compound 567



A215
Compound 568



A216
Compound 569



A217
Compound 570



A218
Compound 571



A219
Compound 572



A220
Compound 573



A221
Compound 574



A222
Compound 575



A223
Compound 576



A224
Compound 577



A225
Compound 578



A226
Compound 579



A227
Compound 580



A228
Compound 581



A229
Compound 582



A230
Compound 583



A231
Compound 584



A232
Compound 585



A233
Compound 586



A234
Compound 587



A235
Compound 588



A236
Compound 589



A237
Compound 590



A238
Compound 591



A239
Compound 592



A240
Compound 593



A241
Compound 594



A242
Compound 595



A243
Compound 596



A244
Compound 597



A245
Compound 598



A246
Compound 599



A247
Compound 600



A248
Compound 601



A249
Compound 602



A250
Compound 605



A251
Compound 606



A252
Compound 607



A253
Compound 608



A254
Compound 609



A255
Compound 610



A256
Compound 611



A257
Compound 612



A258
Compound 613



A259
Compound 614



A260
Compound 616



A261
Compound 617



A262
Compound 618



A263
Compound 619



A264
Compound 620



A265
Compound 621



A266
Compound 622



A267
Compound 623



A268
Compound 624



A269
Compound 625



A274
Compound 630



A275
Compound 631



A276
Compound 632



A277
Compound 633



A278
Compound 634



A279
Compound 635



A280
Compound 636



A281
Compound 637



A282
Compound 638



A283
Compound 639



A284
Compound 640



A285
Compound 641



A286
Compound 642



A287
Compound 643



A288
Compound 644



A289
Compound 645



A290
Compound 646



A291
Compound 647



A292
Compound 648



A293
Compound 649



A294
Compound 650



A295
Compound 651



A296
Compound 652



A297
Compound 653



A298
Compound 654



A299
Compound 655



A300
Compound 656



A301
Compound 657



A302
Compound 658



A303
Compound 659



A304
Compound 660



A305
Compound 661



A306
Compound 662



A307
Compound 663



A308
Compound 664



A309
Compound 665



A310
Compound 666



A311
Compound 667



A312
Compound 668



A313
Compound 674



A314
Compound 675



A315
Compound 676



A316
Compound 677



A317
Compound 678



A318
Compound 679



A319
Compound 680



A320
Compound 681



A321
Compound 682



A322
Compound 683



A323
Compound 684



A324
Compound 685



A325
Compound 686



A326
Compound 687



A327
Compound 688



A328
Compound 689



A329
Compound 690



A330
Compound 691



A331
Compound 692



A332
Compound 693



A333
Compound 694



A334
Compound 695



A335
Compound 696



A336
Compound 697



A337
Compound 698



A338
Compound 699



A339
Compound 700



A340
Compound 701



A341
Compound 702



A342
Compound 703



A343
Compound 704



A344
Compound 705



A345
Compound 706



A350
Compound 711



A351
Compound 712



A352
Compound 713



A353
Compound 714



A354
Compound 715



A355
Compound 716



A 356
Compound 717



A 357
Compound 718



A 358
Compound 719



A 359
Compound 720



A 360
Compound 721



A 361
Compound 722



A 362
Compound 723



A 363
Compound 724



A 364
Compound 725



A 365
Compound 726



A 366
Compound 727



A 367
Compound 728



A 368
Compound 729



A 369
Compound 730



A 370
Compound 731



A 371
Compound 732



A 372
Compound 733



A 373
Compound 734



A 374
Compound 735



A 375
Compound 736



A 376
Compound 737



A 377
Compound 738



A 378
Compound 739



A 379
Compound 740



A 380
Compound 741



A 381
Compound 742



A 382
Compound 743



A 383
Compound 744



A 384
Compound 745



A 385
Compound 746



A 386
Compound 747



A 387
Compound 748



A 388
Compound 749



A 389
Compound 750



A 390
Compound 751



A 391
Compound 752



A 392
Compound 753



A 393
Compound 754



A 394
Compound 755



A 395
Compound 756



A 396
Compound 757



A 397
Compound 758



A 398
Compound 759



A 399
Compound 760



A 400
Compound 761



A 401
Compound 762



A 402
Compound 763



A 403
Compound 764



A 404
Compound 765



A 405
Compound 766



A 406
Compound 767



A 407
Compound 768



A 408
Compound 769



A 409
Compound 770



A 410
Compound 771



A 411
Compound 772



A 412
Compound 773



A 413
Compound 774



A 414
Compound 775



A 415
Compound 776



A 416
Compound 777



A 417
Compound 778



A 418
Compound 779



A 419
Compound 780



A 420
Compound 781



A 421
Compound 782



A 422
Compound 783



A 423
Compound 784



A 424
Compound 785



A 425
Compound 786



A 426
Compound 787



A 427
Compound 788



A 428
Compound 789



A 429
Compound 790



A 430
Compound 791



A 431
Compound 792



A 432
Compound 793



A 433
Compound 794



A 434
Compound 795



A 435
Compound 796



A 436
Compound 797



A 437
Compound 798



A 438
Compound 799



A 439
Compound 800



A 440
Compound 801



A 441
Compound 802



A 442
Compound 803



A 443
Compound 804



A 444
Compound 805



A 445
Compound 806



A 446
Compound 807



A 447
Compound 808



A 448
Compound 809



A 449
Compound 810



A 450
Compound 811



A 451
Compound 812



A 452
Compound 813



A 453
Compound 814



A 454
Compound 815



A 455
Compound 816



A 456
Compound 817



A 457
Compound 818



A 458
Compound 819



A 459
Compound 820



A 460
Compound 821



A 461
Compound 822



A 462
Compound 823



A 463
Compound 824



A 464
Compound 825



A 465
Compound 826



A 466
Compound 827



A 467
Compound 828



A 468
Compound 829



A 469
Compound 830



A 470
Compound 831



A 471
Compound 832



A 472
Compound 833



A 473
Compound 834



A 474
Compound 835



A 475
Compound 836



A 476
Compound 837



A 477
Compound 838



A 478
Compound 839



A 479
Compound 840



A 480
Compound 841



A 481
Compound 842



A 482
Compound 843



A 483
Compound 844



A 484
Compound 845



A 485
Compound 846



A 486
Compound 847



A 487
Compound 848



A 488
Compound 849



A 489
Compound 850



A 490
Compound 851



A 491
Compound 852



A 492
Compound 853



A 493
Compound 854



A 494
Compound 855



A 495
Compound 856



A 496
Compound 857



A 497
Compound 858



A 498
Compound 859



A 499
Compound 860



A 500
Compound 861



A 501
Compound 862



A 502
Compound 863



A 503
Compound 864



A 504
Compound 865



A 505
Compound 866



A 506
Compound 867



A 507
Compound 868



A 508
Compound 869



A 509
Compound 870



A 510
Compound 871



A 511
Compound 872



A 512
Compound 873



A 513
Compound 874



A 514
Compound 875



A 515
Compound 876



A 516
Compound 877



A 517
Compound 878



A 518
Compound 879



A 519
Compound 880



A 520
Compound 881



A 521
Compound 882



A 522
Compound 883



A 523
Compound 884



A 524
Compound 885



A 525
Compound 886



A 526
Compound 887



A 527
Compound 888



A 528
Compound 889



A 529
Compound 890



A 530
Compound 891



A 531
Compound 892



A 532
Compound 893



A 533
Compound 894



A 534
Compound 895



A 535
Compound 896



A 536
Compound 897



A 537
Compound 898



A 538
Compound 899



A 539
Compound 900



A 540
Compound 901



A 541
Compound 902



A 542
Compound 903



A 543
Compound 904



A 544
Compound 905



A 545
Compound 906



A 546
Compound 907



A 547
Compound 908



A 548
Compound 909



A 549
Compound 910



A 550
Compound 911



A 551
Compound 912



A 552
Compound 913



A 553
Compound 914



A 554
Compound 915



A 555
Compound 916



A 556
Compound 917



A 557
Compound 918



A 558
Compound 919



A 559
Compound 920



A 560
Compound 921



A 561
Compound 922



A 562
Compound 923



A 563
Compound 924



A 564
Compound 925



A 565
Compound 926



A 566
Compound 927



A 567
Compound 928



A 568
Compound 929



A 569
Compound 930



A 570
Compound 931



A 571
Compound 932



A 572
Compound 933



A 573
Compound 934



A 574
Compound 935



A 575
Compound 936



A 576
Compound 937



A 577
Compound 938



A 578
Compound 939



A 579
Compound 940



A 580
Compound 941



A 581
Compound 942



A 582
Compound 943



A 583
Compound 944



A 584
Compound 945



A 585
Compound 946



A 586
Compound 947



A 587
Compound 948



A 588
Compound 949



A 589
Compound 950



A 590
Compound 951



A 591
Compound 952



A 592
Compound 953



A 593
Compound 954



A 594
Compound 955



A 595
Compound 956



A 596
Compound 957



A 597
Compound 958



A 598
Compound 959



A 599
Compound 960



A 600
Compound 961



A 601
Compound 962



A 602
Compound 963



A 603
Compound 964



A 604
Compound 965



A 605
Compound 966



A 606
Compound 967



A 607
Compound 968



A 608
Compound 969



A 609
Compound 970



A 610
Compound 971



A 611
Compound 972



A 612
Compound 973



A 613
Compound 974



A 614
Compound 975



A 615
Compound 976



A 616
Compound 977



A 617
Compound 978



A 618
Compound 979



A 619
Compound 980



A 620
Compound 981



A 621
Compound 982



A 622
Compound 983



A 623
Compound 984



A 624
Compound 985



A 625
Compound 986



A 626
Compound 987



A 627
Compound 988



A 628
Compound 989



A 629
Compound 990



A 630
Compound 991



A 631
Compound 992



A 632
Compound 993



A 633
Compound 994



A 634
Compound 995



A 635
Compound 996



A 636
Compound 997



A 637
Compound 998



A 638
Compound 999



A 639
Compound 1000



A 640
Compound 1001



A 641
Compound 1002



A 642
Compound 1003



A 643
Compound 1004



A 644
Compound 1005



A 645
Compound 1006



A 646
Compound 1007



A 647
Compound 1008



A 648
Compound 1009



A 649
Compound 1010



A 650
Compound 1011



A 651
Compound 1012



A 652
Compound 1013



A 653
Compound 1014



A 654
Compound 1015



A 655
Compound 1016



A 656
Compound 1017



A 657
Compound 1018



A 658
Compound 1019



A 659
Compound 1020



A 660
Compound 1021



A 661
Compound 1022



A 662
Compound 1023



A 663
Compound 1024



A 664
Compound 1025



A 665
Compound 1026



A 666
Compound 1027



A 667
Compound 1028



A 668
Compound 1029



A 669
Compound 1030



A 670
Compound 1031



A 671
Compound 1032



A 672
Compound 1033



A 673
Compound 1034



A 674
Compound 1035



A 675
Compound 1036



A 676
Compound 1037



A 677
Compound 1038



A 678
Compound 1039



A 679
Compound 1040



A 680
Compound 1041



A 681
Compound 1042



A 682
Compound 1043



A 683
Compound 1044



A 684
Compound 1045



A 685
Compound 1046



A 686
Compound 1047



A 687
Compound 1048



A 688
Compound 1049



A 689
Compound 1050



A 690
Compound 1051



A 691
Compound 1052



A 692
Compound 1053



A 693
Compound 1054



A 694
Compound 1055



A 695
Compound 1056



A 696
Compound 1057



A 697
Compound 1058



A 698
Compound 1059



A 699
Compound 1060



A 700
Compound 1061



A 701
Compound 1062



A 702
Compound 1063



A 703
Compound 1064



A 704
Compound 1065



A 705
Compound 1066



A 706
Compound 1067



A 707
Compound 1068



A 708
Compound 1069



A 709
Compound 1070



A 710
Compound 1071



A 711
Compound 1072



A 712
Compound 1073



A 713
Compound 1074



A 714
Compound 1075



A 715
Compound 1076



A 716
Compound 1077



A 717
Compound 1078



A 718
Compound 1079



A 719
Compound 1080



A 720
Compound 1081



A 721
Compound 1082



A 722
Compound 1083



A 723
Compound 1084



A 724
Compound 1085



A 725
Compound 1086



A 726
Compound 1087



A 727
Compound 1088



A 728
Compound 1089



A 729
Compound 1090



A 730
Compound 1091



A 731
Compound 1092



A 732
Compound 1093



A 733
Compound 1094



A 734
Compound 1095



A 735
Compound 1096



A 736
Compound 1097



A 737
Compound 1098



A 738
Compound 1099



A 739
Compound 1100



A 740
Compound 1101



A 741
Compound 1102



A 742
Compound 1103



A 743
Compound 1104



A 744
Compound 1105



A 745
Compound 1106



A 746
Compound 1107



A 747
Compound 1108



A 748
Compound 1109



A 749
Compound 1110



A 750
Compound 1111



A 751
Compound 1112



A 752
Compound 1113



A 753
Compound 1114



A 754
Compound 1115



A 755
Compound 1116



A 756
Compound 1117



A 757
Compound 1118



A 758
Compound 1119



A 759
Compound 1120



A 760
Compound 1121



A 761
Compound 1122



A 762
Compound 1123



A 763
Compound 1124



A 764
Compound 1125



A 765
Compound 1126



A 766
Compound 1127



A 767
Compound 1128



A 768
Compound 1129



A 769
Compound 1130



A 770
Compound 1131



A 771
Compound 1132



A 772
Compound 1133



A 773
Compound 1134



A 774
Compound 1135



A 775
Compound 1136



A 776
Compound 1137



A 777
Compound 1138



A 778
Compound 1139



A 779
Compound 1140



A 780
Compound 1141



A 781
Compound 1142



A 782
Compound 1143



A 783
Compound 1144



A 784
Compound 1145



A 785
Compound 1146



A 786
Compound 1147



A 787
Compound 1148



A 788
Compound 1149



A 789
Compound 1150



A 790
Compound 1151



A 791
Compound 1152



A 792
Compound 1153



A 793
Compound 1154



A 794
Compound 1155



A 795
Compound 1156



A 796
Compound 1157



A 797
Compound 1158



A 798
Compound 1159



A 799
Compound 1160



A 800
Compound 1161



A 801
Compound 1162



A 802
Compound 1163



A 803
Compound 1164



A 804
Compound 1165



A 805
Compound 1166



A 806
Compound 1167



A 807
Compound 1168



A 808
Compound 1169



A 809
Compound 1170



A 810
Compound 1171



A 811
Compound 1172



A 812
Compound 1173



A 813
Compound 1174



A 814
Compound 1175



A 815
Compound 1176



A 816
Compound 1177



A 817
Compound 1178



A 818
Compound 1179



A 819
Compound 1180



A 820
Compound 1181



A 821
Compound 1182



A 822
Compound 1183



A 823
Compound 1184



A 824
Compound 1185



A 825
Compound 1186



A 826
Compound 1187



A 827
Compound 1188



A 828
Compound 1189



A 829
Compound 1190



A 830
Compound 1191



A 831
Compound 1192



A 832
Compound 1193



A 833
Compound 1194



A 834
Compound 1195



A 835
Compound 1196



A 836
Compound 1197



A 837
Compound 1198



A 838
Compound 1199



A 839
Compound 1200



A 840
Compound 1201



A 841
Compound 1202



A 842
Compound 1203



A 843
Compound 1204



A 844
Compound 1205



A 845
Compound 1206



A 846
Compound 1207



A 847
Compound 1208



A 848
Compound 1209



A 849
Compound 1210



A 850
Compound 1211



A 851
Compound 1212



A 852
Compound 1213



A 853
Compound 1214



A 854
Compound 1215



A 855
Compound 1216



A 856
Compound 1217



A 857
Compound 1218



A 858
Compound 1219



A 859
Compound 1220



A 860
Compound 1221



A 861
Compound 1222



A 862
Compound 1223



A 863
Compound 1224



A 864
Compound 1225



A 865
Compound 1226



A 866
Compound 1227



A 867
Compound 1228



A 868
Compound 1229



A 869
Compound 1230



A 870
Compound 1231



A 871
Compound 1232



A 872
Compound 1233



A 873
Compound 1234



A 874
Compound 1235



A 875
Compound 1236



A 876
Compound 1237



A 877
Compound 1238



A 878
Compound 1239



A 879
Compound 1240



A 880
Compound 1241



A 881
Compound 1242



A 882
Compound 1243



A 883
Compound 1244



A 884
Compound 1245



A 885
Compound 1246



A 886
Compound 1247



A 887
Compound 1248



A 888
Compound 1249



A 889
Compound 1250



A 890
Compound 1251



A 891
Compound 1252



A 892
Compound 1253



A 893
Compound 1254



A 894
Compound 1255



A 895
Compound 1256



A 896
Compound 1257



A 897
Compound 1258



A 898
Compound 1259



A 899
Compound 1260



A 900
Compound 1261



A 901
Compound 1262



A 902
Compound 1263



A 903
Compound 1264



A 904
Compound 1265



A 905
Compound 1266



A 906
Compound 1267



A 907
Compound 1268



A 908
Compound 1269



A 909
Compound 1270



A 910
Compound 1271



A 911
Compound 1272



A 912
Compound 1273



A 913
Compound 1274



A 914
Compound 1275



A 915
Compound 1276



A 916
Compound 1277



A 917
Compound 1278



A 918
Compound 1279



A 919
Compound 1280



A 920
Compound 1281



A 921
Compound 1282



A 922
Compound 1283



A 923
Compound 1284



A 924
Compound 1285



A 925
Compound 1286



A 926
Compound 1287



A 927
Compound 1288



A 928
Compound 1289



A 929
Compound 1290



A 930
Compound 1291



A 931
Compound 1292



A 932
Compound 1293



A 933
Compound 1294



A 934
Compound 1295



A 935
Compound 1296



A 936
Compound 1297



A 937
Compound 1298



A 938
Compound 1299



A 939
Compound 1300



A 940
Compound 1301



A 941
Compound 1302



A 942
Compound 1303



A 943
Compound 1304



A 944
Compound 1305



A 945
Compound 1306



A 946
Compound 1307



A 947
Compound 1308



A 948
Compound 1309



A 949
Compound 1310



A 950
Compound 1311



A 951
Compound 1312



A 952
Compound 1313



A 953
Compound 1314



A 954
Compound 1315



A 955
Compound 1316



A 956
Compound 1317



A 957
Compound 1318



A 958
Compound 1319



A 959
Compound 1320



A 960
Compound 1321



A 961
Compound 1322



A 962
Compound 1323



A 963
Compound 1324



A 964
Compound 1325



A 965
Compound 1326



A 966
Compound 1327



A 967
Compound 1328



A 968
Compound 1329



A 969
Compound 1330



A 970
Compound 1331



A 971
Compound 1332



A 972
Compound 1333



A 973
Compound 1334



A 974
Compound 1335



A 975
Compound 1336



A 976
Compound 1337



A 977
Compound 1338



A 978
Compound 1339



A 979
Compound 1340



A 980
Compound 1341



A 981
Compound 1342



A 982
Compound 1343



A 983
Compound 1344



A 984
Compound 1345



A 985
Compound 1346



A 986
Compound 1347



A 987
Compound 1348



A 988
Compound 1349



A 989
Compound 1350



A 990
Compound 1351



A 991
Compound 1352



A 992
Compound 1353



A 993
Compound 1354



A 994
Compound 1355



A 995
Compound 1356



A 996
Compound 1357



A 997
Compound 1358



A 998
Compound 1359



A 999
Compound 1360



A 1000
Compound 1361



A 1001
Compound 1362



A 1002
Compound 1363



A 1003
Compound 1364



A 1004
Compound 1365



A 1005
Compound 1366



A 1006
Compound 1367



A 1007
Compound 1368



A 1008
Compound 1369



A 1009
Compound 1370



A 1010
Compound 1371



A 1011
Compound 1372



A 1012
Compound 1373



A 1013
Compound 1374



A 1014
Compound 1375



A 1015
Compound 1376



A 1016
Compound 1377



A 1017
Compound 1378



A 1018
Compound 1379



A 1019
Compound 1380



A 1020
Compound 1381



A 1021
Compound 1382



A 1022
Compound 1383



A 1023
Compound 1384



A 1024
Compound 1385



A 1025
Compound 1386



A 1026
Compound 1387



A 1027
Compound 1388



A 1028
Compound 1389



A 1029
Compound 1390



A 1030
Compound 1391



A 1031
Compound 1392



A 1032
Compound 1393



A 1033
Compound 1394



A 1034
Compound 1395



A 1035
Compound 1396



A 1036
Compound 1397



A 1037
Compound 1398



A 1038
Compound 1399



A 1039
Compound 1400



A 1040
Compound



A 1041
Compound



A 1042
Compound 1401



A 1043
Compound



A 1044
Compound



A 1045
Compound 1402



A 1046
Compound



A 1047
Compound



A 1048
Compound 1403



A 1049
Compound 1404



A 1050
Compound 1405



A 1051
Compound 1406



A 1052
Compound 1407



A 1053
Compound 1408



A 1054
Compound 1409



A 1055
Compound 1410



A 1056
Compound 1411



A 1057
Compound 1412



A 1058
Compound 1413



A 1059
Compound 1414



A 1060
Compound 1415



A 1061
Compound 1416



A 1062
Compound 1417



A 1063
Compound 1418



A 1064
Compound 1419



A 1065
Compound 1420



A 1066
Compound 1421



A 1067
Compound 1422



A 1068
Compound 1423



A 1069
Compound 1424



A 1070
Compound 1425



A 1071
Compound 1426



A 1072
Compound 1427



A 1073
Compound 1428



A 1074
Compound 1429



A 1075
Compound 1430



A 1076
Compound 1431



A 1077
Compound 1432



A 1078
Compound 1433



A 1079
Compound 1434



A 1080
Compound 1435



A 1081
Compound 1436



A 1082
Compound 1437



A 1083
Compound 1438



A 1084
Compound 1439



A 1085
Compound 1440



A 1086
Compound 1441



A 1087
Compound 1442



A 1088
Compound 1443



A 1089
Compound 1444



A 1090
Compound 1445



A 1091
Compound 1446



A 1092
Compound 1447



A 1093
Compound 1448



A 1094
Compound 1449



A 1095
Compound 1450



A 1096
Compound 1451



A 1097
Compound 1452



A 1098
Compound 1453



A 1099
Compound 1454



A 1100
Compound 1455



A 1101
Compound 1456



A 1102
Compound 1457



A 1103
Compound 1458



A 1104
Compound 1459



A 1105
Compound 1460



A 1106
Compound 1461



A 1107
Compound 1462



A 1108
Compound 1463



A 1109
Compound 1464



A 1110
Compound 1465



A 1111
Compound 1466



A 1112
Compound 1467



A 1113
Compound 1468



A 1114
Compound 1469



A 1115
Compound 1470



A 1116
Compound 1471



A 1117
Compound 1472



A 1118
Compound 1473



A 1119
Compound 1474



A 1120
Compound 1475



A 1121
Compound 1476



A 1122
Compound 1477



A 1123
Compound 1478



A 1124
Compound 1479



A 1125
Compound 1480



A 1126
Compound 1481



A 1127
Compound 1482



A 1128
Compound 1483



A 1129
Compound 1484



A 1130
Compound 1485



A 1131
Compound 1486



A 1132
Compound 1487



A 1133
Compound 1488



A 1134
Compound 1489



A 1135
Compound 1490



A 1136
Compound 1491



A 1137
Compound 1492



A 1138
Compound 1493



A 1139
Compound 1494



A 1140
Compound 1495



A 1141
Compound 1496



A 1142
Compound 1497



A 1143
Compound 1498



A 1144
Compound 1499



A 1145
Compound 1500



A 1146
Compound 1501



A 1147
Compound 1502



A 1148
Compound 1503



A 1149
Compound 1504



A 1150
Compound 1505



A 1151
Compound 1506



A 1152
Compound 1507



A 1153
Compound 1508



A 1154
Compound 1509



A 1155
Compound 1510



A 1156
Compound 1511



A 1157
Compound 1512



A 1158
Compound 1513



A 1159
Compound 1514



A 1160
Compound 1515



A 1161
Compound 1516



A 1162
Compound 1517



A 1163
Compound 1518



A 1164
Compound 1519



A 1165
Compound 1520



A 1166
Compound 1521



A 1167
Compound 1522



A 1168
Compound 1523



A 1169
Compound 1524



A 1170
Compound 1525



A 1171
Compound 1526



A 1172
Compound 1527



A 1173
Compound 1528



A 1174
Compound 1529



A 1175
Compound 1530



A 1176
Compound 1531



A 1177
Compound 1532



A 1178
Compound 1533



A 1179
Compound 1534



A 1180
Compound 1535



A 1181
Compound 1536



A 1182
Compound 1537



A 1183
Compound 1538



A 1184
Compound 1539



A 1185
Compound 1540



A 1186
Compound 1541



A 1187
Compound 1542



A 1188
Compound 1543



A 1189
Compound 1544



A 1190
Compound 1545



A 1191
Compound 1546



A 1192
Compound 1547



A 1193
Compound 1548



A 1194
Compound 1549



A 1195
Compound 1550



A 1196
Compound 1551



A 1197
Compound 1552



A 1198
Compound 1553



A 1199
Compound 1554



A 1200
Compound 1555



A 1201
Compound 1556



A 1202
Compound 1557



A 1203
Compound 1558



A 1204
Compound 1559



A 1205
Compound 1560



A 1206
Compound 1561



A 1207
Compound 1562



A 1208
Compound 1563



A 1209
Compound 1564



A 1210
Compound 1565



A 1211
Compound 1566



A 1212
Compound 1567



A 1213
Compound 1568



A 1214
Compound 1569



A 1215
Compound 1570



A 1216
Compound 1571



A 1217
Compound 1572



A 1218
Compound 1573



A 1219
Compound 1574



A 1220
Compound 1575



A 1221
Compound 1576



A 1222
Compound 1577



A 1223
Compound 1578



A 1224
Compound 1579



A 1225
Compound 1580



A 1226
Compound 1581



A 1227
Compound 1582



A 1228
Compound 1583



A 1229
Compound 1584



A 1230
Compound 1585



A 1231
Compound 1586



A 1232
Compound 1587



A 1233
Compound 1588



A 1234
Compound 1589



A 1235
Compound 1590



A 1236
Compound 1591



A 1237
Compound 1592



A 1238
Compound 1593



A 1239
Compound 1594



A 1240
Compound 1595



A 1241
Compound 1596



A 1242
Compound 1597



A 1243
Compound 1598



A 1244
Compound 1599



A 1245
Compound 1600



A 1246
Compound 1601



A 1247
Compound 1602



A 1248
Compound 1603



A 1249
Compound 1604



A 1250
Compound 1605



A 1251
Compound 1606



A 1252
Compound 1607



A 1253
Compound 1608



A 1254
Compound 1609



A 1255
Compound 1610



A 1256
Compound 1611



A 1257
Compound 1612



A 1258
Compound 1613



A 1259
Compound 1614



A 1260
Compound 1615



A 1261
Compound 1616



A 1262
Compound 1617



A 1263
Compound 1618



A 1264
Compound 1619



A 1265
Compound 1620



A 1266
Compound 1621



A 1267
Compound 1622



A 1268
Compound 1623



A 1269
Compound 1624



A 1270
Compound 1625



A 1271
Compound 1626



A 1272
Compound 1627



A 1273
Compound 1628



A 1274
Compound 1629



A 1275
Compound 1630



A 1276
Compound 1631



A 1277
Compound 1632



A 1278
Compound 1633



A 1279
Compound 1634



A 1280
Compound 1635



A 1281
Compound 1636



A 1282
Compound 1637



A 1283
Compound 1638



A 1284
Compound 1639



A 1285
Compound 1640



A 1286
Compound 1641



A 1287
Compound 1642



A 1288
Compound 1643



A 1289
Compound 1644



A 1290
Compound 1645



A 1291
Compound 1646



A 1292
Compound 1647



A 1293
Compound 1648



A 1294
Compound 1649



A 1295
Compound 1650



A 1296
Compound 1651



A 1297
Compound 1652



A 1298
Compound 1653



A 1299
Compound 1654



A 1300
Compound 1655



A 1301
Compound 1656



A 1302
Compound 1657



A 1303
Compound 1658



A 1304
Compound 1659



A 1305
Compound 1660



A 1306
Compound 1661



A 1307
Compound 1662



A 1308
Compound 1663



A 1309
Compound 1664



A 1310
Compound 1665



A 1311
Compound 1666



A 1312
Compound 1667



A 1313
Compound 1668



A 1314
Compound 1669



A 1315
Compound 1670



A 1316
Compound 1671



A 1317
Compound 1672



A 1318
Compound 1673



A 1319
Compound 1674



A 1320
Compound 1675



A 1321
Compound 1676



A 1322
Compound 1677



A 1323
Compound 1678



A 1324
Compound 1679



A 1325
Compound 1680



A 1326
Compound 1681



A 1327
Compound 1682



A 1328
Compound 1683



A 1329
Compound 1684



A 1330
Compound 1685



A 1331
Compound 1686



A 1332
Compound 1687



A 1333
Compound 1688



A 1334
Compound 1689



A 1335
Compound 1690



A 1336
Compound 1691



A 1337
Compound 1692



A 1338
Compound 1693



A 1339
Compound 1694



A 1340
Compound 1695



A 1341
Compound 1696



A 1342
Compound 1697



A 1343
Compound 1698



A 1344
Compound 1699



A 1345
Compound 1700



A 1346
Compound 1701



A 1347
Compound 1702



A 1348
Compound 1703



A 1349
Compound 1704



A 1350
Compound 1705



A 1351
Compound 1706



A 1352
Compound 1707



A 1353
Compound 1708



A 1354
Compound 1709



A 1355
Compound 1710



A 1356
Compound 1711



A 1357
Compound 1712



A 1358
Compound 1713



A 1359
Compound 1714



A 1360
Compound 1715



A 1361
Compound 1716



A 1362
Compound 1717



A 1363
Compound 1718



A 1364
Compound 1719



A 1365
Compound 1720



A 1366
Compound 1721



A 1367
Compound 1722



A 1368
Compound 1723



A 1369
Compound 1724



A 1370
Compound 1725



A 1371
Compound 1726



A 1372
Compound 1727



A 1373
Compound 1728



A 1374
Compound 1729



A 1375
Compound 1730



A 1376
Compound 1731



A 1377
Compound 1732



A 1378
Compound 1733



A 1379
Compound 1734



A 1380
Compound 1735



A 1381
Compound 1736



A 1382
Compound 1737



A 1383
Compound 1738



A 1384
Compound 1739



A 1385
Compound 1740



A 1386
Compound 1741



A 1387
Compound 1742



A 1388
Compound 1743



A 1389
Compound 1744



A 1390
Compound 1745



A 1391
Compound 1746



A 1392
Compound 1747



A 1393
Compound 1748



A 1394
Compound 1749



A 1395
Compound 1750



A 1396
Compound 1751



A 1397
Compound 1752



A 1398
Compound 1753



A 1399
Compound 1754



A 1400
Compound 1755



A 1401
Compound 1756



A 1402
Compound 1757



A 1403
Compound 1758



A 1404
Compound 1759



A 1405
Compound 1760



A 1406
Compound 1761



A 1407
Compound 1762



A 1408
Compound 1763



A 1409
Compound 1764



A 1410
Compound 1765



A 1411
Compound 1766



A 1412
Compound 1767



A 1413
Compound 1768



A 1414
Compound 1769



A 1415
Compound 1770



A 1416
Compound 1771



A 1417
Compound 1772



A 1418
Compound 1773



A 1419
Compound 1774



A 1420
Compound 1775



A 1421
Compound 1776



A 1422
Compound 1777



A 1423
Compound 1778



A 1424
Compound 1779



A 1425
Compound 1780



A 1426
Compound 1781



A 1427
Compound 1782



A 1428
Compound 1783



A 1429
Compound 1784



A 1430
Compound 1785



A 1431
Compound 1786



A 1432
Compound 1787



A 1433
Compound 1788



A 1434
Compound 1789



A 1435
Compound 1790



A 1436
Compound 1791



A 1437
Compound 1792



A 1438
Compound 1793



A 1439
Compound 1794



A 1440
Compound 1795



A 1441
Compound 1796



A 1442
Compound 1797



A 1443
Compound 1798



A 1444
Compound 1799



A 1445
Compound 1800



A 1446
Compound 1801



A 1447
Compound 1802



A 1448
Compound 1803



A 1449
Compound 1804



A 1450
Compound 1805



A 1451
Compound 1806



A 1452
Compound 1807



A 1453
Compound 1808



A 1454
Compound 1809



A 1455
Compound 1810



A 1456
Compound 1811



A 1457
Compound 1812



A 1458
Compound 1813



A 1459
Compound 1814



A 1460
Compound 1815



A 1461
Compound 1816



A 1462
Compound 1817



A 1463
Compound 1818



A 1464
Compound 1819



A 1465
Compound 1820



A 1466
Compound 1821



A 1467
Compound 1822



A 1468
Compound 1823



A 1469
Compound 1824



A 1470
Compound 1825



A 1471
Compound 1826



A 1472
Compound 1827



A 1473
Compound 1828



A 1474
Compound 1829



A 1475
Compound 1830



A 1476
Compound 1831



A 1477
Compound 1832



A 1478
Compound 1833



A 1479
Compound 1834



A 1480
Compound 1835



A 1481
Compound 1836



A 1482
Compound 1837



A 1483
Compound 1838



A 1484
Compound 1839



A 1485
Compound 1840



A 1486
Compound 1841



A 1487
Compound 1842



A 1488
Compound 1843



A 1489
Compound 1844



A 1490
Compound 1845



A 1491
Compound 1846



A 1492
Compound 1847



A 1493
Compound 1848



A 1494
Compound 1849



A 1495
Compound 1850



A 1496
Compound 1851



A 1497
Compound 1852



A 1498
Compound 1853



A 1499
Compound 1854



A 1500
Compound 1855



A 1501
Compound 1856



A 1502
Compound 1857



A 1503
Compound 1858



A 1504
Compound 1859



A 1505
Compound 1860



A 1506
Compound 1861



A 1507
Compound 1862



A 1508
Compound 1863



A 1509
Compound 1864



A 1510
Compound 1865



A 1511
Compound 1866



A 1512
Compound 1867



A 1513
Compound 1868



A 1514
Compound 1869



A 1515
Compound 1870



A 1516
Compound 1871



A 1517
Compound 1872



A 1518
Compound 1873



A 1519
Compound 1874









In some embodiments, a mixture of a compound of this disclosure with a herbicide selected from the group consisting of chlorimuron-ethyl, nicosulfuron, mesotrione, thifensulfuron-methyl, flupyrsulfuron-methyl, tribenuron, pyroxasulfone, pinoxaden, tembotrione, pyroxsulam, metolachlor and S-metolachlorfor is used for better control of undesired vegetation (e.g., lower use rate such as from synergism, broader spectrum of weeds controlled, or enhanced crop safety) or for preventing the development of resistant weeds.


The following Tests demonstrate the control efficacy of compounds of this disclosure on specific pathogens. The pathogen control protection afforded by the compounds is not limited, however, to these species. See Index Tables A-F for compound descriptions. The following abbreviations are used in the Index Tables which follow: Me is methyl, allyl is —CH2CH═CH2, allyl(2-C1) is —CH2CCl═CH2, allyl(3-C1) is —CH2CH═CHCl, allyl(3-Ph) is —CH2CH═CHPh, allyl(3-Br) is —CH2CH═CHBr, allyl(2-Me) is —CH2CMe=CH2, allyl(3,3-di-Me) is —CH2CH═CMe2, “acn” means acetonitrile (—CH2CN) 1-c-hexen is 1-cyclohexenyl, Ph is phenyl, OMe is methoxy, —CN is cyano, —NO2 is nitro and TMS is trimethylsilyl, s is secondary, n is normal, i is iso, c is cyclo, Et is ethyl, Pr is propyl, i Pr is isopropyl, Bu is butyl, c-Pr is cyclopropyl, OEt is ethoxy, and NO2 is nitro. Mass spectra are reported as the molecular weight of the highest isotopic abundance parent ion (M+1) formed by addition of H+ (molecular weight of 1) to the molecule, or (M−1) formed by the loss of H+ (molecular weight of 1) from the molecule, observed by using liquid chromatography coupled to a mass spectrometer (LCMS) using either atmospheric pressure chemical ionization (AP+) or electrospray ionization (ESI+).









INDEX TABLE A (1)









embedded image

















Cmpd. No.
Q1
Q2
m.p. (° C.)
M − 1
M + 1





352
pyridin-3-yl
Ph(2-CF3)
165-168




353 (trans)
Ph(3-NH2)
Ph(2,3-di-F)


332


354 (cis)
Ph(3-NH2)
Ph(2,3-di-F)


332


355
Ph(3,4-di-F)
Ph(2-NH2,3-CH3)

344



356
furan-3-yl
Ph(2-F)
135-138




357
Ph(3,4-di-F)
Ph(2-NH2,3-NO2)

375
377


358
Ph(3,4-di-F)
Ph(2-NH2,3,4-di-F)

366
368


359 (trans)
Ph(3-NMe2)
Ph(2-F)


342


360 (cis)
Ph(3-NMe2)
Ph(2-F)


342


361
Ph(3,4-di-F)
1H-Pyrazol-3-yl(4-Br)

385
387


362
Ph(3,4-di-F)
1H-Pyrazol-5-yl(1-Me)

319
321


363
pyridin-3-yl
Ph(2-F)
179-182




364
furan-3-yl
Ph(2-CF3)


339


365
Ph(4-Ph)
Ph(2-F)


375


366
Ph(4-Ph)
Ph(2,3-di-F)


393


367
Ph(4-Ph)
Ph(2-CF3)


425


368
Ph(3-F,4-Me)
Ph(2-F)


331


369
Ph(3-F,4-Me)
Ph(2,3-di-F)


349


370
Ph(3-F,4-Me)
Ph(2,4-di-F)


349


371
Ph(3-F,4-Me)
Ph(2,3,4-tri-F)


367


372
Ph(3-Me)
Ph(2-F)

311



373
Ph(3-Me)
Ph(2,3-di-F)


331


374
Ph(3-Me)
Ph(2-CF3)


363


375
Ph(3-F)
Ph(2,3-di-F)

333



376
Ph(3-F)
Ph(2-CF3)


367


377
Ph(3-O—i-Pr)
Ph(2,4-di-F)

373
375


379
Ph(2-Ph)
Ph(2,3-di-F)
129-132




380
Ph(3-O—n-Pr)
Ph(2,3-di-F)
138-141




381
Ph(2-Ph)
Ph(2-F)
127-130




382
Ph(2-Ph)
Ph(2,3,4-tri-F)
161-164




383
Ph(3-OMe)
Ph(2,3-di-F)
183-186




384
Ph(3-OH)
Ph(2,3-di-F)
176-179




386
Ph(3-CF3)
Ph(2,4-di-F,3-OMe)


415


387
Ph(3-(2,2 di-F-ethoxy))
Ph(2-F)


379


388
Ph(3-(2,2 di-F-ethoxy))
Ph(2,4-di-F)


397


389
Ph(3-(2,2 di-F-ethoxy))
Ph(2,3-di-F)


397


390
Ph(3-(2,2 di-F-ethoxy))
Ph(2-Cl)


395


391
Ph(3-OCF2CHF2)
Ph(2-CHF2)


447


394
CH3C(O)—
Ph(2,3-di-F)

357



400
Ph(4-F,3-Me)
Ph(2,3-di-F)


349


401
Ph(4-F,3-Me)
Ph(2,3,4-tri-F)


367


407
Ph(3-(2,2 di-F-ethoxy))
Ph(2,3,4-tri-F)


415


408
Ph(3,4-di-F)
Ph(2-F-5-Me)


349


409
Ph(3,4-di-F)
Ph(2-F,3-Me)


349


410
Ph(3,4-di-F)
Ph(2-F,4-Cl)


369


411
Ph(3,4-di-F)
Ph(2-Cl,4-F)


369


412
Ph(3,4-di-F)
Ph(4-F,3-Me)


349


413
Ph(3,4-di-F)
Ph(2-F,4-OMe)


365


414
Ph(3,4-di-F)
Ph(4-CF3,3-Me)


399


415
Ph(3,4-di-F)
Ph(3-F,4-OMe)


365


416
Ph(3,4-di-F)
Ph(2-F,3-OMe)


365


417
Ph(3,4-di-F)
Ph(2-CO2Me)


375


418
Ph(3,4-di-F)
Ph(2-C(O)Me)


359


419
Ph(3,4-di-F)
Ph(2,4-di-F,3-OMe)


383


420
Ph(3-OCHF2)
Ph(2-F,3-Me)

377
379


421
Ph(3-OCHF2)
Ph(2,4-di-F)


383


422
Ph(3-OCHF2)
Ph(3-OCHF2)


413


423
Ph(3-OCHF2)
Ph(2-F,5-Me)


379


424
Ph(3-OCHF2)
Ph(4-F,3-Me)


379


425
Ph(3-OCHF2)
Ph(2-F,4-OMe)
 95-100




426
Ph(3-OCHF2)
Ph(2-F,3-OMe)


395


427
Ph(3-OCHF2)
Ph(2-OCHF2)


413


432
Ph(3-OC(O)CH3)
Ph(2,3-di-F)
147-150




446
Ph(4-Br)
Ph(2,3-di-F)


396


447
Ph(4-Br)
Ph(2,4-di-F)


396


448
Ph(4-Br)
Ph(2-F)


377


449
Ph(4-Br)
Ph(3-F)

375
377


451
Ph(3-C≡C—Ph)
Ph(2,3-di-F)

415
417


452
Ph(4-Br)
Ph(2-S(O)2Me)


436


453
Ph(4-Br)
Ph(2-Cl)


394


455
Ph(2,4-di-F)
Ph(2,3-di-F)


353


460
Ph(3-OCF2CHF2)
Ph(2,4-di-F,3-Me)


447


461
Ph(3,5-di-F)
Ph(2,4-di-F,3-Me)


367


462
Ph(3-F,4-Me)
Ph(2,4-di-F,3-Me)


363


463
Ph(3-CF3)
Ph(2,4-di-F,3-Me)


399


466
Ph(4-Et)
Ph(2-F)


327


467
Ph(4-Et)
Ph(2,3-di-F)


345


468
Ph(4-Et)
Ph(2-S(O)2Me)


387


469
Ph(4-i-Pr)
Ph(2-F)


341


470
Ph(4-i-Pr)
Ph(2,3-di-F)


359


475
Ph(2-F,4-CF3)
Ph(2,3-di-F)


402


487
Ph(2,3-di-F)
Ph(2,3-di-F)


353


488
Ph(3-F,5-CF3)
Ph(2,3-di-F)
146




489
Ph(3-F,5-CF3)
Ph(2-F)
145-149




490
Ph(3-F,5-CF3)
Ph(2,4-di-F)
172-178




491
Ph(3-F,5-Cl)
Ph(2-F)
179-208




492
Ph(3-F,5-Cl)
Ph(2,3-di-F)
122-129




493
Ph(3-F,5-Cl)
Ph(2,4-di-F)
139-147




494
Ph(2,3-di-F)
Ph(2-F)


335


495
Ph(2,3-di-F)
Ph(2,4-di-F)


353


496
Ph(3-CH2OMe)
Ph(2-F)


343


497
Ph(3-CH2OMe)
Ph(2,3-di-F)


361


498
Ph(3-CH2OMe)
Ph(2-Cl)


359


499
Ph(3-CH2OMe)
Ph(2,4-di-F)


361


500
Ph(4-i-Pr)
Ph(2-S(O)2Me)


401


501
Ph(4-c-Pr)
Ph(2,3-di-F)


357


502
Ph(4-c-Pr)
Ph(2-S(O)2Me)


399


504
Ph(3-F,4-CF3)
Ph(2,3-di-F)


403


507
Ph(2-F,4-Me)
Ph(2-S(O)2Me)


391


508
Ph(2-F,4-Me)
Ph(2,4-di-F)


349


509
Ph(2-F,4-Me)
Ph(2-F)


331


510
thiophen-2-yl(4-Br)
Ph(2,3-di-F)


402


513
pyridine-4-yl(2-CF3)
Ph(2-F)


368


514
pyridine-4-yl(2-CF3)
Ph(2,3-di-F)


386


515
Ph(2,6-di-F)
Ph(2-F)


335


516
Ph(2,6-di-F)
Ph(2,3-di-F)


353


517
Ph(2,6-di-F)
Ph(2,4-di-F)


353


518
Ph(2,4-di-F)
Ph(2,4-di-F)


353


519
Ph(3-Br)
Ph(2-F)


391


521
Ph(3-F,4-CF3)
Ph(2-F)


385


522
Ph(3-F,4-CF3)
Ph(2,4-di-F)


403


532
thiophen-3-yl(2,4,5-tri-Br)
Ph(2-F)


542


533
thiophen-3-yl(2,4,5-tri-Br)
Ph(2,3-di-F)


561


534
Ph(4-OPh)
Ph(2-F)





535
Ph(4-OPh)
Ph(2,4-di-F)


409


536
Ph(4-OPh)
Ph(2,3-di-F)


409


537
Ph(4-OPh)
Ph(2,3,4-tri-F)


427


538
Ph(4-OPh)
Ph(2-Cl)


407


540
Ph(3-OCF2CHF2)
Ph(2,4-di-F,3-OMe)


463


541
Ph(3,5-di-F)
Ph(2,4-di-F,3-OMe)


383


544
Ph(2,5-di-F)
Ph(2-F)


335


545
Ph(2,5-di-F)
Ph(2,4-di-F)


353


546
Ph(2,5-di-F)
Ph(2,3-di-F)


353


549
Ph(2,4,5-tri-F)
Ph(2-F)


353


550
Ph(2,4,5-tri-F)
Ph(2,3-di-F)


371


551
Ph(2,4,5-tri-F)
Ph(2,4-di-F)


371


552
Ph(3-O—i-Pr)
Ph(2-F)

355
357


553
Ph(3-O—i-Pr)
Ph(2,3-di-F)

373
375


554
Ph(3-O—i-Pr)
Ph(2,3,4-tri-F)

391
393


555
Ph(4-CF3)
Ph(2-OH)
150-176




556
Ph(4-CF3)
Ph(2-F,6-OH)
197-205




557
Ph(3-CF3)
Ph(2-OH)
 55-66




561
Ph(4-OCHF2)
Ph(2,3-di-F)


383


578
Ph(4-Br,3-Me)
Ph(2-F)


391


579
Ph(4-Br,3-Me)
Ph(2,3-di-F)


410


580
Ph(3-F,4-OMe)
Ph(2-CF3)


397


581
thiophen-2-yl
Ph(2-F)


305


582
thiophen-2-yl
Ph(2,3-di-F)


323


583
thiophen-2-yl(5-Br)
Ph(2-F)


384


584
thiophen-2-yl(5-Br)
Ph(2,3-di-F)


403


587
Ph(3,5-di-CF3)
Ph(2-F)
132-150




588
Ph(3,5-di-CF3)
Ph(2,3-di-F)
112-124




589
Ph(3,5-di-CF3)
Ph(2,4-di-F)
163-167




590
Ph(2-F,3-CF3)
Ph(2-F)
111-115




591
Ph(2-F,3-CF3)
Ph(2,3-di-F)
138-141




592
Ph(2-F—3-CF3)
Ph(2,4-di-F)
134-140




593
Ph(2-F—5-CF3)
Ph(2-F)
126-128




594
Ph(2-F—5-CF3)
Ph(2,3-di-F)
119-120




595
Ph(2-F—5-CF3)
Ph(2,4-di-F)
124-126




597
thiophen-3-yl(2-Br)
Ph(2-F)


384


598
thiophen-3-yl(2-Br)
Ph(2,3-di-F)


403


599
thiophen-3-yl(2-Cl)
Ph(2-F)


339


600
thiophen-3-yl(2-Cl)
Ph(2,3-di-F)


357


601
thiophen-3-yl(2,5-di-Cl)
Ph(2,3-di-F)


392


608
Ph(4-CF3)
Ph(2-S(O)2Me)


423


609
Ph(4-CF3)
Ph(2-F)


363


610
Ph(4-CF3)
Ph(2,3-di-F)


381


614
Ph(2,4,5-tri-F)
Ph(2,3,4-tri-F)


389


620
Ph(2,4-di-F)
Ph(2-F)

333
335


621
Ph(3-CN)
Ph(2,3-di-F)


342


630
thiophen-3-yl(5-Me)
Ph(2-F)
128-131




634
Ph(3-CF3)
Ph(2-S(O)2NH2)


428


635
1,3-benzodioxol-5-yl(2,2-di-F)
Ph(2,3-di-F)


397


642
Ph(3-CF3,4-Me)
Ph(2,3-di-F)


399


648
thiophen-3-yl(5-Br)
Ph(2-F)


385


649
thiophen-3-yl(5-Br)
Ph(2,3-di-F)


403


654
Ph(3-CF3,4-Me)
Ph(2-F)

379
381


655
Ph(3-CF3,4-Me)
Ph(2,4-di-F)


399


656
thiophen-3-yl(5-Me)
Ph(2,3-di-F)
144-148




657
thiophen-3-yl(5-Et)
Ph(2-F)
 96-99




658
thiophen-3-yl(5-Et)
Ph(2,3-di-F)
113-117




674
Ph(3-CF3)
Ph(2-F,3-OMe)


397


675
Ph(3-CF3)
Ph(2-F,4-Cl)


401


676
Ph(3-CF3)
Ph(2-Cl,4-F)


401


677
Ph(3-C≡CH)
Ph(2,3-di-F)

339



678
Ph(3-CF3,4-Me)
Ph(2-F)


381


679
Ph(3-CF3,4-Me)
Ph(2,3-di-F)


399


680
Ph(3-CF3,4-Me)
Ph(2,4-di-F)


399


681
Ph(3-CF3,4-Me)
Ph(2,3,4-tri-F)


417


686
Ph(3-Br)
Ph(2-F)


377


687
Ph(3-Br)
Ph(2,4-di-F)


395


688
Ph(3-Br)
Ph(2,3-di-F)


395


689
Ph(3-Br)
Ph(2,3,4-tri-F)


413


695
Ph(3-OCF2CHF2)
Ph(2-F)


415


696
Ph(3-OCF2CHF2)
Ph(2,4-di-F)


433


697
Ph(3-OCF2CHF2)
Ph(2,3-di-F)


433


698
Ph(3-OCF2CHF2)
Ph(2,3,4-tri-F)


451


699
Ph(3-OCF2CHF2)
Ph(2-Cl)


431


700
Ph(4-I)
Ph(2,3-di-F)


443


701
Ph(4-I)
Ph(2,4-di-F)


443


702
Ph(4-I)
Ph(2-F)


425


703
Ph(4-I)
Ph(3-F)


425


704
Ph(4-I)
Ph(2-Cl)


441


705
Ph(3-CF3)
Ph(2-CO2Me)


407


706
Ph(3-CF3)
Ph(2-C(O)Me)


391


711
Naphthalene-1-yl
Ph(2,3-di-F)


367


712
Naphthalene-1-yl
Ph(2-CF3)


399


714
Ph(3-OH)
Ph(2-F)


315


715
Ph(3-OH)
Ph(2,3-di-F)


333


716
Ph(3-OH)
Ph(2-CF3)


365






(1) Substituents in the 3 and 4 positions of the pyrrolidinone ring when, i.e. C(O)N(Q2)(R6) (when Y2 is O) and Q1, respectively, are predominately in the trans configuration. In some instances the presence of minor amounts of the cis isomer can be detected by NMR.














INDEX TABLE B









embedded image


















Cmpd No.
R1
Q1
R5
R6
Q2
M + 1





378
Me
Ph(3-O—i-Pr)
H
H
Ph(2,4-di-F)
389


392
Me
Ph(3-OCF2CHF2)
H
H
Ph(2,3-di-F)
447


393
Me
Ph(3-OCF2CHF2)
H
H
Ph(2,4-di-F)
447


395
Me
Ph(3-C≡CH)
OH
H
Ph(2,3-di-F)
357


396
Me
Ph(3-F,4-CF3)
H
H
Ph(2,3-di-F)
417


397
Me
Ph(3-F,4-CF3)
H
H
Ph(2-S(O)2Me)
459


398
Me
Ph(3-F,4-CF3)
H
H
Ph(2,4-di-F)
417


399
Me
Ph(3-F,4-CF3)
H
H
Ph(2-F)
399


402
Me
Ph(4-F,3-Me)
H
H
Ph(2-F)
345


403
Me
Ph(4-F,3-Me)
H
H
Ph(2,3-di-F)
363


404
Me
Ph(4-F,3-Me)
H
H
Ph(2,4-di-F)
363


405
Me
Ph(4-F,3-Me)
H
H
Ph(2-S(O)2Me)
405


406
Me
Ph(4-F,3-Me)
H
H
Ph(2-CF3)
395


428
Me
Ph(3-CF3)
Me
H
Ph(2-F)
395


429
Me
Ph(3-OCF2CHF2)
H
H
Ph(2,3,4-tri-F)
465


430
Me
Ph(3-OCF2CHF2)
H
H
Ph(2,4-di-F,3-OMe)
477


431
Me
Ph(3-OCF2CHF2)
H
H
Ph(2-CF3)
479


433
Me
Ph(4-Cl)
H
H
Ph(2-F)
347


434
Me
Ph(4-Cl)
H
H
Ph(2,3-di-F)
365


435
Me
Ph(4-Cl)
H
H
Ph(2-S(O)2Me)
407


436
Me
Ph(4-Cl)
H
H
Ph(2,4-di-F)
365


437
Me
Ph(4-F)
H
H
Ph(2-F)
331


438
Me
Ph(4-F)
H
H
Ph(2,3-di-F)
349


439
Me
Ph(4-F)
H
H
Ph(2-S(O)2Me)
391


440
Me
Ph(4-F)
H
H
Ph(2,4-di-F)
349


441
Me
1,3-benzodioxol-5-
H
H
Ph(2-F)
393




yl(2,2-di-F)






442
Me
1,3-benzodioxol-5-
H
H
Ph(2,3-di-F)
411




yl(2,2-di-F)






443
Me
1,3-benzodioxol-5-
H
H
Ph(2-S(O)2Me)
453




yl(2,2-di-F)






444
Me
1,3-benzodioxol-5-
H
H
Ph(2,4-di-F)
411




yl(2,2-di-F)






445
Me
Ph(3-CF3)
H
Ph(2-F)
Ph(2-F)
518


456
Ph
Ph(3-CF3)
H
H
Ph(2-F)
441*


457
Ph
Ph(3-CF3)
H
H
Ph(2,3-di-F)
459*


464
Me
Ph(3-F,4-Me)
H
H
Ph(2,3-di-F)
363


465
Me
Ph(3-F,4-Me)
H
H
Ph(2-F)
345


472
Me
Ph(2-F,4-CF3)
H
H
Ph(2,3-di-F)
417


473
Me
Ph(2-F,4-CF3)
H
H
Ph(2-S(O)2Me)
459


474
Me
Ph(2-F,4-CF3)
H
H
Ph(2,4-di-F)
417


476
Me
Ph(2-F,4-CF3)
H
H
Ph(2-F)
399


477
allyl(3,3-di-
Ph(3-CF3)
H
H
Ph(2,3-di-F)
451*



Me)







478
allyl(3,3-di-
Ph(3-CF3)
H
H
Ph(2-F)
433*



Me)







479
allyl(2-Me)
Ph(3-CF3)
H
H
Ph(2,3-di-F)
438*


480
allyl(2-Cl)
Ph(3-CF3)
H
H
Ph(2,3-di-F)
457*


481
allyl(2-Me)
Ph(3-CF3)
H
H
Ph(2-F)
419*


482
allyl(2-Cl)
Ph(3-CF3)
H
H
Ph(2-F)
439*


483
allyl(3-Cl)
Ph(3-CF3)
H
H
Ph(2-F)
439*


484
allyl(3-Br)
Ph(3-CF3)
H
H
Ph(2-F)
485*


485
allyl(3-Cl)
Ph(3-CF3)
H
H
Ph(2,3-di-F)
457*


486
allyl(3-Br)
Ph(3-CF3)
H
H
Ph(2,3-di-F)
503*


503
—C(O)Me
Ph(3-CF3)
H
H
Ph(2-F)



505
Ph(4-OMe)
Ph(3-CF3)
H
H
Ph(2-F)
473


506
Ph(4-CN)
Ph(3-CF3)
H
H
Ph(2-F)
406


511
allyl(3-Ph)
Ph(3,5-di-F)
H
H
Ph(2,3-di-F)
469


512
allyl(3-Cl)
Ph(3,5-di-F)
H
H
Ph(2,3-di-F)
427


520
Me
Ph(3-Br)
H
H
Ph(2,3-di-F)
409


523
Me
Ph(3-OCHF2)
H
H
Ph(2-S(O)2Me)
439


524
1-c-hexen-3-
Ph(3-CF3)
H
H
Ph(2-F)
445*



yl







525
1-c-hexen-3-
Ph(3-CF3)
H
H
Ph(2,3-di-F)
463*



yl







526
allyl(3-Br)r
Ph(3-CF3)
H
H
Ph(2-F)
485*


527
allyl(3-Br)r
Ph(3-CF3)
H
H
Ph(2,3-di-F)
503*


528
Me
Ph(3-F,4-Me)
H
H
Ph(2,4-di-F)
363


529
Me
Ph(3-F,4-Me)
H
H
Ph(2,3,4-tri-F)
381


530
Me
Ph(3-F,4-Me)
H
H
Ph(2-S(O)2Me)
405


531
Me
Ph(3-F,4-Me)
H
H
Ph(2-CF3)
395


539
Me
Ph(3-OCF2CHF2)
H
H
Ph(2-F)
429


547
Me
Ph(2,6-di-F)
H
H
Ph(2,3-di-F)
367


558
Me
Ph(2-F,4-Me)
H
H
Ph(2-S(O)2Me)
405


559
Me
Ph(2-F,4-Me)
H
H
Ph(2,4-di-F)
363


560
Me
Ph(2-F,4-Me)
H
H
Ph(2-F)
345


562
Me
Ph(4-OCHF2)
H
H
Ph(2,3-di-F)
397


563
Me
Ph(4-Br)
H
H
Ph(2-F)
391


564
Me
Ph(4-Br)
H
H
Ph(2,3-di-F)
409


565
Me
Ph(4-Br)
H
H
Ph(2-S(O)2Me)
451


566
Me
Ph(4-Br)
H
H
Ph(2,4-di-F)
409


567
Me
Ph(3-Et)
H
H
Ph(2-F)
341


568
Me
Ph(3-Et)
H
H
Ph(2,3-di-F)
359


569
Me
Ph(3-Et)
H
H
Ph(2-S(O)2Me)
401


570
Me
Ph(3-Et)
H
H
Ph(2,4-di-F)
359


571
Me
Ph(3-CF3)
H
H
Ph(2,4-di-F)
399


572
Me
Ph(3-CF3)
H
H
Ph(2-NO2)
408


573
Me
Ph(3-CF3)
H
H
Ph(3-F,2-Me)
395


574
Me
Ph(3-CF3)
H
H
Ph(2-F,3-Cl)
415


575
Me
Ph(3-CF3)
H
H
Ph(4-F,2-Me)
395


576
Me
Ph(3-CF3)
H
H
Ph(2-F,3-CN)
406


577
Me
Ph(3-CF3)
H
H
Ph
363


585
Me
thiophen-2-yl(5-Me)
H
H
Ph(2-F)
332


586
Me
thiophen-2-yl(5-Me)
H
H
Ph(2,3-di-F)
351


596
Me
Ph(3,4-di-F)
H
H
Ph(2-F)
**


602
Ph(4-NO2)
Ph(3-CF3)
H
H
Ph(2-F)
488


605
allyl
Ph(3-CF3)
H
H
Ph(2-F)
407


606
allyl
Ph(3-CF3)
H
H
Ph(2,3-di-F)
425


607
—CH2C≡CH
Ph(3-CF3)
H
H
Ph(2-F)
405


611
Me
Ph(4-F,3-CF3)
H
H
Ph(2-F)
399


612
Me
Ph(4-F,3-CF3)
H
H
Ph(2-S(O)2Me)
459


613
Me
Ph(4-F,3-CF3)
H
H
Ph(2,3-di-F)
417


616
Me
Ph(3-OCHF2)
H
H
Ph(2,3-di-F)
395*


617
Me
Ph(3-OCHF2)
H
H
Ph(2,4-di-F)
397


618
Me
Ph(3-OCHF2)
H
H
Ph(2-F)
379


619
Me
Ph(3-OCHF2)
Me
H
Ph(2,3-di-F)
411


622
Me
Ph(4-CF3)
H
H
Ph(2-F)
381


623
Me
Ph(4-CF3)
H
H
Ph(2,3-di-F)
399


624
Me
Ph(4-CF3)
H
H
Ph(2-S(O)2Me)
441


625
Me
Ph(4-CF3)
H
H
Ph(2,4-di-F)
399


631
H
Ph(3-O-allyl)
allyl
H
Ph(2,3-di-F)
411*


632
Me
Ph(3-F)
H
H
Ph(2,3-di-F)
349


633
Me
Ph(3-F)
H
H
Ph(2,4-di-F)
349


636
Me
Ph(3-CF3)
H
H
Ph(2,3-di-F)
399


637
Me
Ph(3-CF3)
H
H
Ph(2-S(O)2Me)
441


638
Me
Ph(3-CF3)
H
H
Ph(2-CF3)
431


639
Me
Ph(3,4-di-F)
H
H
Ph(2,3-di-F)
367


640
Me
Ph(3,4-di-F)
H
H
Ph(2-S(O)2Me)
409


641
Me
Ph(3,4-di-F)
H
H
Ph(2-CF3)
399


643
Me
Ph(3,5-di-F)
H
H
Ph(2-F)
349


644
Me
Ph(3,5-di-F)
H
H
Ph(2,3-di-F)
367


645
Me
Ph(3,5-di-F)
H
H
Ph(2,4-di-F)
367


646
Me
Ph(3,5-di-F)
H
H
Ph(2,3,4-tri-F)
385


647
Me
Ph(3,5-di-F)
H
H
Ph(2-CF3)
399


650
Me
Ph(3-O—i-Pr)
H
H
Ph(2-F)
371


651
Me
Ph(3-O—i-Pr)
H
H
Ph(2,3-di-F)
390


652
Me
Ph(3-O—i-Pr)
H
H
Ph(2-CF3)
422


653
Me
Ph(3-O—i-Pr)
H
H
Ph(2-S(O)2Me)
432


659
Me
Ph(3,5-di-F)
H
H
Inden(2,3-dihydro)-4-
371







yl



660
Me
Ph(3,5-di-F)
H
H
Naph(5,6,7,8-
385







tetrahydro)-1-yl



661
Me
Ph(4-Me)
H
H
Ph(2-F)
327


662
Me
Ph(4-Me)
H
H
Ph(2,3-di-F)
345


663
Me
Ph(4-Me)
H
H
Ph(2-S(O)2Me)
387


664
Me
Ph(4-Me)
H
H
Ph(2,4-di-F)
345


665
Me
Ph(4-Me)
H
H
Ph(2-CF3)
377


666
Me
Ph(3-Me)
H
H
Ph(2-F)
327


667
Me
Ph(3-Me)
H
H
Ph(2,3-di-F)
345


668
Me
Ph(3-Me)
H
H
Ph(2-S(O)2Me)
387


682
—CH2—c-Pr
Ph(3-CF3)
H
H
Ph(2-F)
422


683
—CH2—c-Pr
Ph(3-CF3)
H
H
Ph(2,3-di-F)
440


684
c-Pr
Ph(3-CF3)
H
H
Ph(2-F)
408


685
c-Pr
Ph(3-CF3)
H
H
Ph(2,3-di-F)
426


690
Me
Ph(4-CF2CH3)
H
H
Ph(2,3-di-F)
395


691
Me
Ph(4-CF2CH3)
H
H
Ph(2-F)
377


692
Me
Ph(4-CF2CH3)
H
H
Ph(2-S(O)2Me)
437


693
Me
Ph(4-CF2CH3)
H
H
Ph(2,4-di-F)
395


694
Me
Ph(3-CF3)
Et
H
Ph(2,3-di-F)
427


713
H
Ph(3,4-di-F)
H
acn
Ph(2-NO2)





*M − 1.


**M.P. = 116-120° C.


***M.P. = 183-186° C.













INDEX TABLE C









embedded image



















Cmpd. No.
R1
Q1
R4
R5
R6
Q2
m.p. (° C.)





454
H
Ph(3-CF3)
H
H
H
Ph(2,3-di-F)
162-166


















INDEX TABLE D











embedded image


















Cmpd. No.
Q1
Q2
m.p. (° C.)







450
Ph(4-CF3)
Ph(2-F)
109-112



471
Ph
Ph(2-F)


















INDEX TABLE E





Ex #
Structure
















717


embedded image







718


embedded image







719


embedded image







720


embedded image







721


embedded image







722


embedded image







723


embedded image







724


embedded image







725


embedded image







726


embedded image







727


embedded image







728


embedded image







729


embedded image







730


embedded image







731


embedded image







732


embedded image







733


embedded image







734


embedded image







735


embedded image







736


embedded image







737


embedded image







738


embedded image







739


embedded image







740


embedded image







741


embedded image







742


embedded image







743


embedded image







744


embedded image







745


embedded image







746


embedded image







747


embedded image







748


embedded image







749


embedded image







750


embedded image







751


embedded image







752


embedded image







753


embedded image







754


embedded image







755


embedded image







756


embedded image







757


embedded image







758


embedded image







759


embedded image







760


embedded image







761


embedded image







762


embedded image







763


embedded image







764


embedded image







765


embedded image







766


embedded image







767


embedded image







768


embedded image







769


embedded image







770


embedded image







771


embedded image







772


embedded image







773


embedded image







774


embedded image







775


embedded image







776


embedded image







777


embedded image







778


embedded image







779


embedded image







780


embedded image







781


embedded image







782


embedded image







783


embedded image







784


embedded image







785


embedded image







786


embedded image







787


embedded image







788


embedded image







789


embedded image







790


embedded image







791


embedded image







792


embedded image







793


embedded image







794


embedded image







795


embedded image







796


embedded image







797


embedded image







798


embedded image







799


embedded image







800


embedded image







801


embedded image







802


embedded image







803


embedded image







804


embedded image







805


embedded image







806


embedded image







807


embedded image







808


embedded image







809


embedded image







810


embedded image







811


embedded image







812


embedded image







813


embedded image







814


embedded image







815


embedded image







816


embedded image







817


embedded image







818


embedded image







819


embedded image







820


embedded image







821


embedded image







822


embedded image







823


embedded image







824


embedded image







825


embedded image







826


embedded image







827


embedded image







828


embedded image







829


embedded image







830


embedded image







831


embedded image







832


embedded image







833


embedded image







834


embedded image







835


embedded image







836


embedded image







837


embedded image







838


embedded image







839


embedded image







840


embedded image







841


embedded image







842


embedded image







843


embedded image







844


embedded image







845


embedded image







846


embedded image







847


embedded image







848


embedded image







849


embedded image







850


embedded image







851


embedded image







852


embedded image







853


embedded image







854


embedded image







855


embedded image







856


embedded image







857


embedded image







858


embedded image







859


embedded image







860


embedded image







861


embedded image







862


embedded image







863


embedded image







864


embedded image







865


embedded image







866


embedded image







867


embedded image







868


embedded image







869


embedded image







870


embedded image







871


embedded image







872


embedded image







873


embedded image







874


embedded image







875


embedded image







876


embedded image







877


embedded image







878


embedded image







879


embedded image







880


embedded image







881


embedded image







882


embedded image







883


embedded image







884


embedded image







885


embedded image







886


embedded image







887


embedded image







888


embedded image







889


embedded image







890


embedded image







891


embedded image







892


embedded image







893


embedded image







894


embedded image







895


embedded image







896


embedded image







897


embedded image







898


embedded image







899


embedded image







900


embedded image







901


embedded image







902


embedded image







903


embedded image







904


embedded image







905


embedded image







906


embedded image







907


embedded image







908


embedded image







909


embedded image







910


embedded image







911


embedded image







912


embedded image







913


embedded image







914


embedded image







915


embedded image







916


embedded image







917


embedded image







918


embedded image







919


embedded image







920


embedded image







921


embedded image







922


embedded image







923


embedded image







924


embedded image







925


embedded image







926


embedded image







927


embedded image







928


embedded image







929


embedded image







930


embedded image







931


embedded image







932


embedded image







933


embedded image







934


embedded image







935


embedded image







936


embedded image







937


embedded image







938


embedded image







939


embedded image







940


embedded image







941


embedded image







942


embedded image







943


embedded image







944


embedded image







945


embedded image







946


embedded image







947


embedded image







948


embedded image







949


embedded image







950


embedded image







951


embedded image







952


embedded image







953


embedded image







954


embedded image







955


embedded image







956


embedded image







957


embedded image







958


embedded image







959


embedded image







960


embedded image







961


embedded image







962


embedded image







963


embedded image







964


embedded image







965


embedded image







966


embedded image







967


embedded image







968


embedded image







969


embedded image







970


embedded image







971


embedded image







972


embedded image







973


embedded image







974


embedded image







975


embedded image







976


embedded image







977


embedded image







978


embedded image







979


embedded image







980


embedded image







981


embedded image







982


embedded image







983


embedded image







984


embedded image







985


embedded image







986


embedded image







987


embedded image







988


embedded image







989


embedded image







990


embedded image







991


embedded image







992


embedded image







993


embedded image







994


embedded image







995


embedded image







996


embedded image







997


embedded image







998


embedded image







999


embedded image







1000


embedded image







1001


embedded image







1002


embedded image







1003


embedded image







1004


embedded image







1005


embedded image







1006


embedded image







1007


embedded image







1008


embedded image







1009


embedded image







1010


embedded image







1011


embedded image







1012


embedded image







1013


embedded image







1014


embedded image







1015


embedded image







1016


embedded image







1017


embedded image







1018


embedded image







1019


embedded image







1020


embedded image







1021


embedded image







1022


embedded image







1023


embedded image







1024


embedded image







1025


embedded image







1026


embedded image







1027


embedded image







1028


embedded image







1029


embedded image







1030


embedded image







1031


embedded image







1032


embedded image







1033


embedded image







1034


embedded image







1035


embedded image







1036


embedded image







1037


embedded image







1038


embedded image







1039


embedded image







1040


embedded image







1041


embedded image







1042


embedded image







1043


embedded image







1044


embedded image







1045


embedded image







1046


embedded image







1047


embedded image







1048


embedded image







1049


embedded image







1050


embedded image







1051


embedded image







1052


embedded image







1053


embedded image







1054


embedded image







1055


embedded image







1056


embedded image







1057


embedded image







1058


embedded image







1059


embedded image







1060


embedded image







1061


embedded image







1062


embedded image







1063


embedded image







1064


embedded image







1065


embedded image







1066


embedded image







1067


embedded image







1068


embedded image







1069


embedded image







1070


embedded image







1071


embedded image







1072


embedded image







1073


embedded image







1074


embedded image







1075


embedded image







1076


embedded image







1077


embedded image







1078


embedded image







1079


embedded image







1080


embedded image







1081


embedded image







1082


embedded image







1083


embedded image







1084


embedded image







1085


embedded image







1086


embedded image







1087


embedded image







1088


embedded image







1089


embedded image







1090


embedded image







1091


embedded image







1092


embedded image







1093


embedded image







1094


embedded image







1095


embedded image







1096


embedded image







1097


embedded image







1098


embedded image







1099


embedded image







1100


embedded image







1101


embedded image







1102


embedded image







1103


embedded image







1104


embedded image







1105


embedded image







1106


embedded image







1107


embedded image







1108


embedded image







1109


embedded image







1110


embedded image







1111


embedded image







1112


embedded image







1113


embedded image







1114


embedded image







1115


embedded image







1116


embedded image







1117


embedded image







1118


embedded image







1119


embedded image







1120


embedded image







1121


embedded image







1122


embedded image







1123


embedded image







1124


embedded image







1125


embedded image







1126


embedded image







1127


embedded image







1128


embedded image







1129


embedded image







1130


embedded image







1131


embedded image







1132


embedded image







1133


embedded image







1134


embedded image







1135


embedded image







1136


embedded image







1137


embedded image







1138


embedded image







1139


embedded image







1140


embedded image







1141


embedded image







1142


embedded image







1143


embedded image







1144


embedded image







1145


embedded image







1146


embedded image







1147


embedded image







1148


embedded image







1149


embedded image







1150


embedded image







1151


embedded image







1152


embedded image







1153


embedded image







1154


embedded image







1155


embedded image







1156


embedded image







1157


embedded image







1158


embedded image







1159


embedded image







1160


embedded image







1161


embedded image







1162


embedded image







1163


embedded image







1164


embedded image







1165


embedded image







1166


embedded image







1167


embedded image







1168


embedded image







1169


embedded image







1170


embedded image







1171


embedded image







1172


embedded image







1173


embedded image







1174


embedded image







1175


embedded image







1176


embedded image







1177


embedded image







1178


embedded image







1179


embedded image







1180


embedded image







1181


embedded image







1182


embedded image







1183


embedded image







1184


embedded image







1185


embedded image







1186


embedded image







1187


embedded image







1188


embedded image







1189


embedded image







1190


embedded image







1191


embedded image







1192


embedded image







1193


embedded image







1194


embedded image







1195


embedded image







1196


embedded image







1197


embedded image







1198


embedded image







1199


embedded image







1200


embedded image







1201


embedded image







1202


embedded image







1203


embedded image







1204


embedded image







1205


embedded image







1206


embedded image







1207


embedded image







1208


embedded image







1209


embedded image







1210


embedded image







1211


embedded image







1212


embedded image







1213


embedded image







1214


embedded image







1215


embedded image







1216


embedded image







1217


embedded image







1218


embedded image







1219


embedded image







1220


embedded image







1221


embedded image







1222


embedded image







1223


embedded image







1224


embedded image







1225


embedded image







1226


embedded image







1227


embedded image







1228


embedded image







1229


embedded image







1230


embedded image







1231


embedded image







1232


embedded image







1233


embedded image







1234


embedded image







1235


embedded image







1236


embedded image







1237


embedded image







1238


embedded image







1239


embedded image







1240


embedded image







1241


embedded image







1242


embedded image







1243


embedded image







1244


embedded image







1245


embedded image







1246


embedded image







1247


embedded image







1248


embedded image







1249


embedded image







1250


embedded image







1251


embedded image







1252


embedded image







1253


embedded image







1254


embedded image







1255


embedded image







1256


embedded image







1257


embedded image







1258


embedded image







1259


embedded image







1260


embedded image







1261


embedded image







1262


embedded image







1263


embedded image







1264


embedded image







1265


embedded image







1266


embedded image







1267


embedded image







1268


embedded image







1269


embedded image







1270


embedded image







1271


embedded image







1272


embedded image







1273


embedded image







1274


embedded image







1275


embedded image







1276


embedded image







1277


embedded image







1278


embedded image







1279


embedded image







1280


embedded image







1281


embedded image







1282


embedded image







1283


embedded image







1284


embedded image







1285


embedded image







1286


embedded image







1287


embedded image







1288


embedded image







1289


embedded image







1290


embedded image







1291


embedded image







1292


embedded image







1293


embedded image







1294


embedded image







1295


embedded image







1296


embedded image







1297


embedded image







1298


embedded image







1299


embedded image







1300


embedded image







1301


embedded image







1302


embedded image







1303


embedded image







1304


embedded image







1305


embedded image







1306


embedded image







1307


embedded image







1308


embedded image







1309


embedded image







1310


embedded image







1311


embedded image







1312


embedded image







1313


embedded image







1314


embedded image







1315


embedded image







1316


embedded image







1317


embedded image







1318


embedded image







1319


embedded image







1320


embedded image







1321


embedded image







1322


embedded image







1323


embedded image







1324


embedded image







1325


embedded image







1326


embedded image







1327


embedded image







1328


embedded image







1329


embedded image







1330


embedded image







1331


embedded image







1332


embedded image







1333


embedded image







1334


embedded image







1335


embedded image







1336


embedded image







1337


embedded image







1338


embedded image







1339


embedded image







1340


embedded image







1341


embedded image







1342


embedded image







1343


embedded image







1344


embedded image







1345


embedded image







1346


embedded image







1347


embedded image







1348


embedded image







1349


embedded image







1350


embedded image







1351


embedded image







1352


embedded image







1353


embedded image







1354


embedded image







1355


embedded image







1356


embedded image







1357


embedded image







1358


embedded image







1359


embedded image







1360


embedded image







1361


embedded image







1362


embedded image







1363


embedded image







1364


embedded image







1365


embedded image







1366


embedded image







1367


embedded image







1368


embedded image







1369


embedded image







1370


embedded image







1371


embedded image







1372


embedded image







1373


embedded image







1374


embedded image







1375


embedded image







1376


embedded image







1377


embedded image







1378


embedded image







1379


embedded image







1380


embedded image







1381


embedded image







1382


embedded image







1383


embedded image







1384


embedded image







1385


embedded image







1386


embedded image







1387


embedded image







1388


embedded image







1389


embedded image







1390


embedded image







1391


embedded image







1392


embedded image







1393


embedded image







1394


embedded image







1395


embedded image







1396


embedded image







1397


embedded image







1398


embedded image







1399


embedded image







1400


embedded image







1401


embedded image







1402


embedded image











Characterization Data for Compounds 717-1402

















Ex #
M + 1
M − 1
MP ° C.





















717
331





718
349



719
381



720
349



721
407



722
405



723
437



724
447



725
410



726


108-111



727
339



728
320



729
338



730
363



731
361



732
355.6



733
369.5



734
401.5



735
369.5
367.5



736
385.5
387.5



737
419.5
417.5



738
377.5
375.4



739
409.4
407.4



741


227-231



742
353



743
371



744
202



745
417



746
389



747
403



750
355



751
373



752
306



753
439



754
379



755


135-139



756
389



757
403



758
417.4
415.4



759
367.4
365.4



760
363.4
361.4



767
343



768
411.5
409.5



769
439.5
437.5



770
429.4
427.5



771
381.4
379.5



772


146-150



773


69.5-77



774


133.9-140.7



775
356.4
354.5



776
376.3



779
381



780
423



781
381



782
363



783

348.3



784
471.3
469.4



785
359



786
341



787
425



788
439



789
347



790
365



791
365



792


133-137



793


151-155



795


86-89



796
373.5



797
355.5



798
383.5



799
391



800
370



801
381



802
359



803
363



804
477.3
477.3



805

363.5



806

459.4



807

427.4



808

445.4



809

437.4



810

443.4



811

455.4



812

423.4



813

441.4



814

433.4



815
353



816
371



817
413



818
371



819
355



820
415



821
373



822
331



823
381



824
391



825
394



826
381



827
429



828
381



829
392



830
385



831
399



832
409



833
363



834
381



835
381



836
399



837
403



838
421



839
463



840
421



841
413



842
423



843



844


133-136



845


150-153



846


132-135



847
373



848
367



849
363



850
345



851
373



852
373.3



853
391.3



854
401.3



855
411.3



856
429.3



857
439.3



858
411.3



859
429.3



860
439.3



861
457



862
457



863
473



864
489



865
407



866
395



867
381



868
418.4
416.4



869
400.5
398.5



870
400.5
398.5



871
393.4
391.5



872
393.4
391.5



873
411



874

405



875
393



876
421



877
453



878
367



879
385



881
381



882
399



883
399



884
373



885
355



886


137-140



887


192-195



888
327.4
325.4



889
345.4
343.4



890
417



891
431



892
395



893
413



894
413



895
431



896
445



897
455



898
435



899
417



900
477



901
435



902
359



903
357.3



904
375.2



905
375.2



906

341.5



907

359.5



908

359.5



909
377.5
375.5



910
377.5
339.5



911
359.5
357.5



912
391.5
389.5



913


 96-100



914



915


181-184



916
441



917

343.4



919
469.4



920
455.4



921

377.4



922

359.4



923

419.4



924

393.4



925

437.5



926

453.4



927

479.5



928
361



929
379



930
379



931
397



932
411



933


94-97



934


123-126



935


116-119



936


119-122



937


160-163



938


169-172



939


178-181



940


164-167



941


166-169



942


113-116



943


104-107



944
421



945

327.4



946

345.4



947

347.3



948


115-119



949
343.2



950
361.2



951
361.2



952
371.3



953
389.3



954
389.3



955
357.3



956
375.3



957
391



958
387



959
405



960
373



961
391



962
387



963
375.3



964
371.3



965
389.3



966
389.3



967
345.3
343.5



968
399.4
397.5



969
405.5
403.5



970
336.4
334.5



971
443.5



972
457.5



973


174-176



974
383



975
393



976
365



977
379



978
379



979
423



980
373.3



981
401.3



982
359



983
373



984
411.5
409.5



985
365.4
363.5



986
429.5
427.5



987
389



988
389



989
357



990
439



991
439.5
437.5



992
365.4
363.4



993
435



994
413



995
433



996
407.5
405.5



998
461.5



999
429.5



1000
447.5



1001
439.5



1002
445.4



1003
389.5



1004
407.5



1005
399.5



1006
405.5



1007

345.4



1008
444.5



1009
413.4



1010
431.4



1011


136-140



1012


162-166



1013
379



1014
375



1015
389



1016
405



1017
405



1018
421



1019
407.5
405.5



1020
361.5
359.5



1021
379.4
377.5



1022
389.5
387.5



1023
421.2



1024
439.2



1025
449.2



1026
361



1027
379



1028
385.3



1029
403.3



1030
403.3



1033
327.5



1034
345.5



1035
341.5



1036
355.5



1037
387.5



1038
341.5



1039
359.5



1040
399



1041
441



1042
381



1043
399



1044
398



1045
339.3
338.4



1046
357.3
355.4



1047
383.4
381.4



1048
401.3
399.4



1049
433.3
431.4



1050


66-70



1052


120-124



1053


118-121



1054


192-196



1055


100-104



1056


130-134



1057


159-163



1058


128-132



1059
361.4
359.3



1061


161-165



1062
361



1063
379



1064
433



1065
432



1066
432



1067
378



1068
378



1069
378



1070
324



1071
381



1072


163-167



1074
389.4
387.4



1075
407.4
405.4



1076
417.4
415.4



1077
411



1078
435



1079
409



1080
433



1081
395



1082
419



1083
405



1084
429



1085


113-117



1086


89-93



1087


 98-102



1088
397



1089
383



1090
370



1091
420



1092
394



1093
394



1095
350.7
348.4



1096

364.3



1097
366.3
364.3



1098
405



1099
423



1100
424



1101
442



1102
467



1103
456



1104


192-196



1105


173-176



1109
414.5



1110
432.7



1111
324



1112
320



1113
338



1114
369



1115
387



1116
355



1117
373



1118
355



1119
373



1120
369



1121
387



1122
387



1123
369



1124
381



1125
367



1126
375



1127
411



1129


 97-101



1130


216-220



1132


142-146



1133


119-123



1134


133-137



1135
357.3



1136
375.3



1137
375.3



1138
355.5
353.5



1139
373.5
371.5



1140
363.5
361.5



1143


141-145



1144
383



1147


107.5-115.4



1148


132-136



1149


126-130



1150


137-141



1151
417.3



1152
417.3



1154


102-106



1156


117-121



1159


141-143



1160


161-164



1163
377



1164
363



1165
376.5



1166
403.6



1167
382.5



1168
403.6



1173

413.4



1174

439.4



1175
423



1176
400



1177
341.5



1178
355.5



1181



123-127.7




1182


139.5-153



1183
411.5
409.5



1184
429.5
427.6



1185
439.5
437.5



1186
341



1187
355



1188
352



1189
352



1190
356



1191
342



1192
374



1193
360



1196


144-148



1197
396.5



1198
410.5



1199
342



1200
358



1201
370



1202
397



1203
415



1204
429



1206
342



1207
338



1208
356



1209
391.3



1210
421.3



1211
425



1212
407



1213
393



1214
417



1215
373.3



1216
401.3



1217
403.3



1218
431.3



1219
391.4



1220
359.4



1221
377.4



1222
369.4



1223
375.4



1224
445.4



1225
413.4



1226
431.4



1227
423.4



1228
429.3



1229
374



1230
366



1231
363



1232
355



1233
341



1234
428



1235
345



1236
359



1237


 97-101



1238


138-141



1239


123-127



1240


 52.4-124.1



1245
397



1246
407



1247
345.5
343.6



1248
345.5
343.6



1249
409



1250
449



1251
421



1252
407



1253
363



1254
356



1255
374



1256
386



1257
371



1258


123-127



1260
399



1261
377



1262
369



1263
370



1265
383



1266
401



1267
375



1268
393



1270


88-92



1273


136-140



1274
364



1275
373



1276
391



1277
359



1278
377



1279
379



1282
331



1283
429



1284
429



1285
338



1286
356



1287
374



1288
430



1289
430



1290
416



1291
309



1292
399



1293
431



1294
449



1295
431



1296
449



1297
467



1298
361.4
359.5



1299
379.4
377.5



1300
375.5
373.5



1301
389.4
387.5



1302
421.5
419.5



1303


124-127



1304


166-170



1305
393



1306
359



1307
391



1308
345



1309
349



1310
358



1311
359



1312
373



1313
389



1314
389



1315
411.4



1316
395



1317
377



1318
437



1319
395



1320
401



1321
355



1322
373



1323
391



1324
373



1325
383



1326
349



1327
367



1328
367



1329


81-84



1330


54-57



1331


113-116



1332

373.4



1333
389.4
387.4



1334
429.4



1336


111-142



1337
453.5
451.5



1338
411.4
409.4



1339
429.4
427.4



1340
439.4
437.4



1341


187-191



1342


103-107



1343


130-134



1344
324



1345
328



1346
394



1347
400



1348
400



1349
346



1350
412



1351
390



1352
443



1353
420



1354
444



1355


186-188



1358


180-181



1359


147-149



1362


221-223



1366


81-85



1367
469



1368
445



1369
427



1370
391.3



1371
379



1372
400.5

188.1-192.4



1373
418.5



1374
376



1375
328



1376


146-150



1377
405



1378
363

101.6-102.3



1379
388



1380
406



1381
406



1382


170-173



1383
381



1384
361



1385


139-142



1386


156-160



1387
365.3



1388
373



1389
417



1390


153-156



1392


154-158



1393
428



1394


206-209



1395
431.4



1396
382



1397


382



1398
328



1399
348



1400
382



1402
346


















INDEX TABLE F





Ex. #
Structure







1403


embedded image







1404


embedded image







1405


embedded image







1406


embedded image







1407


embedded image







1408


embedded image







1409


embedded image







1410


embedded image







1411


embedded image







1412


embedded image







1413


embedded image







1414


embedded image







1415


embedded image







1416


embedded image







1417


embedded image







1418


embedded image







1419


embedded image







1420


embedded image







1421


embedded image







1422


embedded image







1423


embedded image







1424


embedded image







1425


embedded image







1426


embedded image







1427


embedded image







1428


embedded image







1429


embedded image







1430


embedded image







1431


embedded image







1432


embedded image







1433


embedded image







1434


embedded image







1435


embedded image







1436


embedded image







1437


embedded image







1438


embedded image







1439


embedded image







1440


embedded image







1441


embedded image







1442


embedded image







1443


embedded image







1444


embedded image







1445


embedded image







1446


embedded image







1447


embedded image







1448


embedded image







1449


embedded image







1450


embedded image







1451


embedded image







1452


embedded image







1453


embedded image







1454


embedded image







1455


embedded image







1456


embedded image







1457


embedded image







1458


embedded image







1459


embedded image







1460


embedded image







1461


embedded image







1462


embedded image







1463


embedded image







1464


embedded image







1465


embedded image







1466


embedded image







1467


embedded image







1468


embedded image







1469


embedded image







1470


embedded image







1471


embedded image







1472


embedded image







1473


embedded image







1474


embedded image







1475


embedded image







1476


embedded image







1477


embedded image







1478


embedded image







1479


embedded image







1480


embedded image







1481


embedded image







1482


embedded image







1483


embedded image







1484


embedded image







1485


embedded image







1486


embedded image







1487


embedded image







1488


embedded image







1489


embedded image







1490


embedded image







1491


embedded image







1492


embedded image







1493


embedded image







1494


embedded image







1495


embedded image







1496


embedded image







1497


embedded image







1498


embedded image







1499


embedded image







1500


embedded image







1501


embedded image







1502


embedded image







1503


embedded image







1504


embedded image







1505


embedded image







1506


embedded image







1507


embedded image







1508


embedded image







1509


embedded image







1510


embedded image







1511


embedded image







1512


embedded image







1513


embedded image







1514


embedded image







1515


embedded image







1516


embedded image







1517


embedded image







1518


embedded image







1519


embedded image







1520


embedded image







1521


embedded image







1522


embedded image







1523


embedded image







1524


embedded image







1525


embedded image







1526


embedded image







1527


embedded image







1528


embedded image







1529


embedded image







1530


embedded image







1531


embedded image







1532


embedded image







1533


embedded image







1534


embedded image







1535


embedded image







1536


embedded image







1537


embedded image







1538


embedded image







1539


embedded image







1540


embedded image







1541


embedded image







1542


embedded image







1543


embedded image







1544


embedded image







1545


embedded image







1546


embedded image







1547


embedded image







1548


embedded image







1549


embedded image







1550


embedded image







1551


embedded image







1552


embedded image







1553


embedded image







1554


embedded image







1555


embedded image







1556


embedded image







1557


embedded image







1558


embedded image







1559


embedded image







1560


embedded image







1561


embedded image







1562


embedded image







1563


embedded image







1564


embedded image







1565


embedded image







1566


embedded image







1567


embedded image







1568


embedded image







1569


embedded image







1570


embedded image







1571


embedded image







1572


embedded image







1573


embedded image







1574


embedded image







1575


embedded image







1576


embedded image







1577


embedded image







1578


embedded image







1579


embedded image







1580


embedded image







1581


embedded image







1582


embedded image







1583


embedded image







1584


embedded image







1585


embedded image







1586


embedded image







1587


embedded image







1588


embedded image







1589


embedded image







1590


embedded image







1591


embedded image







1592


embedded image







1593


embedded image







1594


embedded image







1595


embedded image







1596


embedded image







1597


embedded image







1598


embedded image







1599


embedded image







1600


embedded image







1601


embedded image







1602


embedded image







1603


embedded image







1604


embedded image







1605


embedded image







1606


embedded image







1607


embedded image







1608


embedded image







1609


embedded image







1610


embedded image







1611


embedded image







1612


embedded image







1613


embedded image







1614


embedded image







1615


embedded image







1616


embedded image







1617


embedded image







1618


embedded image







1619


embedded image







1620


embedded image







1621


embedded image







1622


embedded image







1623


embedded image







1624


embedded image







1625


embedded image







1626


embedded image







1627


embedded image







1628


embedded image







1629


embedded image







1630


embedded image







1631


embedded image







1632


embedded image







1633


embedded image







1634


embedded image







1635


embedded image







1636


embedded image







1637


embedded image







1638


embedded image







1639


embedded image







1640


embedded image







1641


embedded image







1642


embedded image







1643


embedded image







1644


embedded image







1645


embedded image







1646


embedded image







1647


embedded image







1648


embedded image







1649


embedded image







1650


embedded image







1651


embedded image







1652


embedded image







1653


embedded image







1654


embedded image







1655


embedded image







1656


embedded image







1657


embedded image







1658


embedded image







1659


embedded image







1660


embedded image







1661


embedded image







1662


embedded image







1663


embedded image







1664


embedded image







1665


embedded image







1666


embedded image







1667


embedded image







1668


embedded image







1669


embedded image







1670


embedded image







1671


embedded image







1672


embedded image







1673


embedded image







1674


embedded image







1675


embedded image







1676


embedded image







1677


embedded image







1678


embedded image







1679


embedded image







1680


embedded image







1681


embedded image







1682


embedded image







1683


embedded image







1684


embedded image







1685


embedded image







1686


embedded image







1687


embedded image







1688


embedded image







1689


embedded image







1690


embedded image







1691


embedded image







1692


embedded image







1693


embedded image







1694


embedded image







1695


embedded image







1696


embedded image







1697


embedded image







1698


embedded image







1699


embedded image







1700


embedded image







1701


embedded image







1702


embedded image







1703


embedded image







1704


embedded image







1705


embedded image







1706


embedded image







1707


embedded image







1708


embedded image







1709


embedded image







1710


embedded image







1711


embedded image







1712


embedded image







1713


embedded image







1714


embedded image







1715


embedded image







1716


embedded image







1717


embedded image







1718


embedded image







1719


embedded image







1720


embedded image







1721


embedded image







1722


embedded image







1723


embedded image







1724


embedded image







1725


embedded image







1726


embedded image







1727


embedded image







1728


embedded image







1729


embedded image







1730


embedded image







1731


embedded image







1732


embedded image







1733


embedded image







1734


embedded image







1735


embedded image







1736


embedded image







1737


embedded image







1738


embedded image







1739


embedded image







1740


embedded image







1741


embedded image







1742


embedded image







1743


embedded image







1744


embedded image







1745


embedded image







1746


embedded image







1747


embedded image







1748


embedded image







1749


embedded image







1750


embedded image







1751


embedded image







1752


embedded image







1753


embedded image







1754


embedded image







1755


embedded image







1756


embedded image







1757


embedded image







1758


embedded image







1759


embedded image







1760


embedded image







1761


embedded image







1762


embedded image







1763


embedded image







1764


embedded image







1765


embedded image







1766


embedded image







1767


embedded image







1768


embedded image







1769


embedded image







1770


embedded image







1771


embedded image







1772


embedded image







1773


embedded image







1774


embedded image







1775


embedded image







1776


embedded image







1777


embedded image







1778


embedded image







1779


embedded image







1780


embedded image







1781


embedded image







1782


embedded image







1783


embedded image







1784


embedded image







1785


embedded image







1786


embedded image







1787


embedded image







1788


embedded image







1789


embedded image







1790


embedded image







1791


embedded image







1792


embedded image







1793


embedded image







1794


embedded image







1795


embedded image







1796


embedded image







1797


embedded image







1798


embedded image







1799


embedded image







1800


embedded image







1801


embedded image







1802


embedded image







1803


embedded image







1804


embedded image







1805


embedded image







1806


embedded image







1807


embedded image







1808


embedded image







1809


embedded image







1810


embedded image







1811


embedded image







1812


embedded image







1813


embedded image







1814


embedded image







1815


embedded image







1816


embedded image







1817


embedded image







1818


embedded image







1819


embedded image







1820


embedded image







1821


embedded image







1822


embedded image







1823


embedded image







1824


embedded image







1825


embedded image







1826


embedded image







1827


embedded image







1828


embedded image







1829


embedded image







1830


embedded image







1831


embedded image







1832


embedded image







1833


embedded image







1834


embedded image







1835


embedded image







1836


embedded image







1837


embedded image







1838


embedded image







1839


embedded image







1840


embedded image







1841


embedded image







1842


embedded image







1843


embedded image







1844


embedded image







1845


embedded image







1846


embedded image







1847


embedded image







1848


embedded image







1849


embedded image







1850


embedded image







1851


embedded image







1852


embedded image







1853


embedded image







1854


embedded image







1855


embedded image







1856


embedded image







1857


embedded image







1858


embedded image







1859


embedded image







1860


embedded image







1861


embedded image







1862


embedded image







1863


embedded image







1864


embedded image







1865


embedded image







1866


embedded image







1867


embedded image







1868


embedded image







1869


embedded image







1870


embedded image







1871


embedded image







1872


embedded image







1873


embedded image







1874


embedded image











Characterization Data for Compounds 1403-1874













Ex. #
M − 1
M + 1

















1403
413
415


1404
361


1405
397
399


1406

413


1407
378
380


1408

380


1409
367
369


1410

391


1411
443


1412
397


1413

402


1414

415


1415

395


1416
391
406


1417
354
388


1418
336


1419
418
382


1420

361


1421

377


1422
387
387


1423
405
422


1424

445


1425
413
426


1426
405
449


1427
387
384


1428
401
382


1429

378


1430
415
421


1431
361
409


1432
361
442


1433
379
389


1434
379
415


1435
413
432


1436
413
450


1437
393
378


1438

385


1439
435
437


1440
435
437


1441
435
437


1442
409
411


1443
447
449


1444
400
402


1445

419


1446

407


1447
425
427


1448

405


1449

403


1450
380
382


1451
465
467


1452

400


1453

373


1454

363


1455

357


1456
427
429


1457

339


1458

400


1459
439
441


1460
403
405


1461
364
366


1462
364
366


1463

380


1464

363


1465
391
393


1466
378
380


1467
450
452


1468
354
356


1469
420
422


1470
462
464


1471
336
338


1472
397
399


1473

397


1474
393
395


1475
377
379


1476

413


1477

396


1478
380
382


1479
435


1480

362


1481

380


1482
348
350


1483
457
459


1484
376
378


1485
432
434


1486
382
384


1487
398
400


1488

375


1489
380
382


1490
387
389


1491
381
383


1492
362
364


1493
378
381


1494
398
400


1495

384


1496

385


1497

398


1498
411
416


1499
371
373


1500

371


1501

381


1502

413


1503

432


1504

438


1505

378


1506

354


1507

398


1508

380


1509

383


1510

435


1511

422


1512

435


1513

354


1514

443


1515

400


1516

411


1517

398


1518

365


1519

432


1520

394


1521

436


1522

395


1523

432


1524

410


1525

398


1526

383


1527

368


1528

395


1529

382


1530

421


1531

368


1532

367


1533

353


1534

354


1535

421


1536

353


1537

423


1538

426


1539

400


1540

422


1541

398


1542

466


1543

379


1544

399


1545

409


1546

426


1547

433


1548

439


1549

394


1550

422


1551

378


1552

399


1553

368


1554

370


1555

382


1556

368


1557

379


1558

399


1559

385


1560

384


1561

399


1562

354


1563

432


1564

365


1565

395


1566

446


1567

433


1568

409


1569

404


1570

384


1571

398


1572

365


1573

353


1574

399


1575

379


1576

408


1577

365


1578

412


1579

368


1580

402


1581

413


1582

392


1583

365


1584
408
410


1585
398
400


1586
440
442


1587

438


1588

381


1589

394


1590

411


1591

395


1592

422


1593

395


1594

476


1595

384


1596

364


1597

369


1598

397


1599

388


1600

378


1601

394


1602

415


1603

400


1604

423


1605

403


1606

398


1607

411


1608

398


1609

449


1610

382


1611

369


1612

355


1613

396


1614

449


1615

367


1616

449


1617

455


1618

369


1619

455


1620

422


1621

427


1622

381


1623

381


1624

403


1625

435


1626

367


1627

433


1628

433


1629

413


1630

392


1631

412


1632

387


1633

387


1634

367


1635

384


1636

422


1637

406


1638

432


1639

442


1640

395


1641

379


1642

412


1643

368


1644

426


1645

422


1646

353


1647

379


1648

379


1649

399


1650

400


1651

429


1652

382


1653

382


1654

396


1655

383


1656

416


1657

383


1658

387


1659

370


1660

367


1661
473
475


1662

347


1663

365


1664

455


1665
467
469


1666
416
418


1667
387
389


1668
405
407


1669
417
419


1670

433


1671
380
382


1672
430
432


1673
382
384


1674
396
398


1675

361


1676
413
415


1677

456


1678
405
407


1679

401


1680

459


1681

442


1682
387
389


1683
401
403


1684

424


1685

410


1686

409


1687

370


1688

375


1689

419


1690

395


1691

370


1692

389


1693

473


1694

440


1695

393


1696

443


1697

445


1698

447


1699

379


1700

393


1701

447


1702

397


1703

401


1704

425


1705

413


1706

397


1707

389


1708

397


1709

413


1710

381


1711

409


1712

377


1713

389


1714

467


1715

389


1716

419


1717

393


1718

447


1719

405


1720

375


1721

439


1722

390


1723

413


1724

407


1725

457


1726

473


1727
399
401


1728

381


1729
407
409


1730
415
417


1731
407
409


1732
446
448


1733
394
396


1734
387
389


1735
387
389


1736

403


1737
451
453


1738
451
453


1739
397
399


1740
398
400


1741
398
400


1742
412
414


1743
412
414


1744
380
382


1745
380
382


1746
440
442


1747
440
442


1748
397
399


1749
408
410


1750
408
410


1751
424
426


1752
424
426


1753

444


1754
455
457


1755
394
396


1756

451


1757
417
419


1758
430
432


1759
413
415


1760
387
398


1761
387
389


1762

357


1763
413
415


1764
423
425


1765
399
401


1766
395
397


1767
387
389


1768
380
382


1769

389


1770
405


1771
409
411


1772
396
398


1773
413
415


1774
361
363


1775
361
363


1776
379
381


1777
379
381


1778
413
415


1779
413
415


1780
427
429


1781
398
400


1782

400


1783

407


1784
438
440


1785
395
397


1786
408
410


1787
437
439


1788
424
426


1789
440
442


1790

415


1791
369
371


1792
411
413


1793
389
391


1794
507
509


1795
453
455


1796
464
466


1797
473
475


1798
414
416


1799
507
509


1800
421
423


1801
394
396


1802
424
426


1803
403
405


1804

389


1805
392
394


1806

397


1807
395
397


1808
395
397


1809
380
382


1810
346
348


1811
364
366


1812
396
398


1813
446
448


1814
396
398


1815
396
398


1816
380
382


1817
380
382


1818

369


1819
383


1820

361


1821
499
501


1822

363


1823
380
382


1824
407
409


1825
410
412


1826
447
449


1827
385


1828

367


1829

424


1830

391


1831

406


1832

420


1833

415


1834
417
419


1835
393
395


1836

415


1837
397
399


1838
397
399


1839
406
408


1840
404
406


1841

364


1842

450


1843

450


1844

370


1845

416


1846

342


1847

407


1848

400


1849

350


1850
413
415


1851
398


1852
473


1853

397


1854
431


1855

398


1856
396


1857
441
443


1858

365


1859
373
375


1860

419


1861

383


1862

366


1863

366


1864
422
424


1865
399


1866
367


1867
451


1868
420
422


1869
423
425


1870
375
377


1871
392
394


1872
401
403


1873

403


1874
436
438









Biological Examples

Test A


Seeds of plant species selected from barnyardgrass (Echinochloa crus-galli), kochia (Kochia scoparia), ragweed (common ragweed, Ambrosia elatior), ryegrass, Italian (Italian ryegrass, Lolium multiflorum), crabgrass, large (Digitaria sanguinalis), giant foxtail (Setaria faberii), green foxtail (Setaria viridis), morningglory (Ipomoea spp.), pigweed (Amaranthus retroflexus), velvetleaf (Abutilon theophrasti), wheat (Triticum aestivum), and corn (Zea mays) were planted into a blend of loam soil and sand and treated preemergence with a directed soil spray using test chemicals formulated in a non-phytotoxic solvent mixture which included a surfactant.


At the same time, plants selected from these crop and weed species and also blackgrass (Alopecurus myosuroides), and galium (catchweed bedstraw, Galium aparine) were planted in pots containing the same blend of loam soil and sand and treated with postemergence applications of test chemicals formulated in the same manner. Plants ranged in height from 2 to 10 cm and were in the one- to two-leaf stage for the postemergence treatment. Treated plants and untreated controls were maintained in a greenhouse for approximately 10 d, after which time all treated plants were compared to untreated controls and visually evaluated for injury. Plant response ratings, summarized in Table A, are based on a 0 to 100 scale where 0 is no effect and 100 is complete control. A dash (-) response means no test result.












TABLE A









1000 g ai/ha
Compounds
















Postemergence
355
357
358
511
512
713
784







Barnyardgrass
0
0
0
90 
80 
0
90 



Blackgrass



20 
0

20 



Corn
0
0
0
0
0
0
0



Crabgrass, Large
0
0
40 


0




Foxtail, Giant
0
0
30 
90 
90 
0
90 




Galium




0
0

0




Kochia




0
0

0



Morningglory
0
0
0


0
0



Pigweed
0
0
0
0
0
0
0



Ragweed



0
0

0



Ryegrass, Italian



0
0

0



Velvetleaf
0
0
0


0




Wheat
0
0
0
0
0
0
0












500 g ai/ha
Compounds




















Postemergence
352
353
354
356
360
361
362
363
364
365
366
367
368





Barnyardgrass
0
0
0
0
0
0
0
0
0
0
0
0
90


Blackgrass












60


Corn
0
0
0
0
0
0
0
0
0
0
0
0
20


Crabgrass, Large
0
0
0
0
0
0
0
0
0
0
0
0



Foxtail, Giant
0
0
0
0
0
0
0
0
0
0
0
0
80



Galium













50



Kochia













 0


Morningglory
0
0
0
0
0
0
0
0
0
0
0
0



Pigweed
0
0
0
0
0
0
0
0
0
0
0
0
 0


Ragweed












30


Ryegrass, Italian












50


Velvetleaf
0
0
0
0
0
0
0
10 
0
0
0
0



Wheat
0
0
0
0
0
0
0
0
0
0
0
0
30











500 g ai/ha
Compounds





















Postemergence
369
370
371
372
373
374
375
376
377
378
379
380
381
382





Barnyardgrass
90
90
90
80
80
90
90
90
90
90
50
80
30
20


Blackgrass
70
40
60
30
40
50
70
40
70
70
0
40
0
0


Corn
50
20
60
20
50
20
80
30
50
80
0
0
0
0


Foxtail, Giant
80
70
90
70
70
50
90
90
80
80
20
70
20
20



Galium

70
60
30
20
30
40
50
30
70
70
0
50
0
0



Kochia

60
0
40
40
40
0
60
20
60
70
0
0
0
0


Pigweed
0
0
20
30
30
0
50
0
30
50
0
0
0
0


Ragweed
30
50
30
0
0
0
20
20
60
50
0
0
0
0


Ryegrass, Italian
50
20
30
40
20
0
20
20
50
70
0
0
0
0


Wheat
60
20
40
20
70
40
80
0
50
50
0
20
0
0











500 g ai/ha
Compounds




















Postemergence
383
384
386
387
388
389
390
391
392
393
394
395
396





Barnyardgrass
90
0
80
70
70
70
70
80
90
90
90
0
90


Blackgrass
0
0
70
50
50
0
0
70
70
70
20
0
60


Corn
0
0
80
0
0
50
0
70
80
80
0
0
80


Foxtail, Giant
50
0
80
70
80
70
80
90
90
90
60
0
90



Galium

0
0
60
0
30
0
0
60
70
70
20
0
60



Kochia

30
0
0
0
0
0
0
60
70
60
0
0
70


Pigweed
0
0
10
0
0
20
20
50
70
70
0
0
70


Ragweed
20
0
30
0
0
0
0
30
20
0
0
0
0


Ryegrass, Italian
30
0
50
0
0
0
10
40
80
70
0
0
70


Wheat
0
0
50
0
0
0
0
50
70
70
0
0
70











500 g ai/ha
Compounds





















Postemergence
397
398
399
400
401
402
403
404
405
406
407
408
409
410





Barnyardgrass
90
90
90
90
90
90
90
90
90
90
70
0
70
50


Blackgrass
70
60
60
60
50
70
60
60
60
50
50
0
20
20


Corn
70
70
70
80
40
80
90
80
80
70
40
0
0
0


Foxtail, Giant
80
90
90
70
70
90
90
90
80
80
70
0
80
40



Galium

60
60
50
60
60
60
60
50
60
50
0
0
0
0



Kochia

50
80
60
70
60
60
60
70
50
50
40
0
30
0


Pigweed
70
60
40
50
40
50
50
60
50
30
0
0
20
20


Ragweed
20
0
0
50
50
60
30
50
50
20
0
0
0
0


Ryegrass, Italian
60
50
40
90
60
50
70
70
60
40
0
0
0
0


Wheat
50
70
60
70
70
80
80
80
80
70
0
0
0
0











500 g ai/ha
Compounds





















Postemergence
411
412
413
414
415
416
417
418
419
420
421
422
423
424





Barnyardgrass
70
0
0
0
0
0
0
0
80
90
90
60
0
70


Blackgrass
0
0
0
0
0
0
0
0
0
0
50
50
0
0


Corn
0
0
0
0
0
0
0
0
20
0
70
0
0
0


Foxtail, Giant
80
0
0
0
0
0
0
0
90
80
90
60
0
70



Galium

50
0
0
0
0
0
0
0
0
0
60
70
0
0



Kochia

0
0
0
10
0
0
0
0
20
0
20
60
0
0


Pigweed
0
0
0
0
0
0
0
0
0
0
30
60
0
0


Ragweed
0
0
0
0
0
0
0
0
0
0
30
0
0
0


Ryegrass, Italian
0
0
0
0
0
0
0
0
20
0
40
0
0
0


Wheat
0
0
0
0
0
0
0
0
20
0
40
0
0
0











500 g ai/ha
Compounds





















Postemergence
425
426
427
428
429
430
431
432
433
434
435
436
437
438





Barnyardgrass
30
70
80
90
90
90
90
30
90
90
90
90
90
90


Blackgrass
0
0
40
70
70
70
60
0
40
50
50
40
30
70


Corn
0
0
20
60
80
70
70
0
30
70
20
40
20
50


Foxtail, Giant
30
60
80
90
90
80
90
30
80
90
80
90
90
90



Galium

0
0
50
60
70
60
60
0
50
60
60
60
50
50



Kochia

0
0
20
70
70
50
50
0
50
70
50
70
30
70


Pigweed
0
0
0
20
80
50
60
0
20
70
50
60
20
60


Ragweed
0
0
20
0
50
30
60
0
50
20
60
20
0
30


Ryegrass, Italian
0
0
20
30
80
50
40
20
60
50
40
50
20
60


Wheat
0
0
20
60
60
50
60
0
60
70
60
40
40
70











500 g ai/ha
Compounds





















Postemergence
439
440
441
442
443
444
445
446
447
448
449
450
451
452





Barnyardgrass
90
90
90
90
80
90
90
90
80
90
80
90
0
70


Blackgrass
60
50
80
70
70
60
60
50
30
30
20
40
0
60


Corn
20
20
70
70
80
70
90
30
0
0
0
60
0
0


Foxtail, Giant
90
90
80
80
80
80
90
90
80
80
80
80
0
80



Galium

50
40
50
60
50
70
60
50
50
50
50
60
0
50



Kochia

70
40
70
60
30
80
30
60
40
50
40
50
0
70


Pigweed
50
20
60
70
50
80
30
60
30
40
20
60
0
70


Ragweed
20
0
50
40
20
40
30
20
0
0
0
30
0
30


Ryegrass, Italian
30
60
60
80
60
80
40
30
20
20
20
50
0
20


Wheat
40
50
80
70
60
50
70
50
0
0
0
30
0
20











500 g ai/ha
Compounds



















Postemergence
453
454
455
456
457
460
461
462
463
464
465
466





Barnyardgrass
80
80
80
0
0
70
90
80
70
90
90
90


Blackgrass
30
50
0
0
0
40
0
40
70
70
70
60


Corn
40
70
0
0
0
40
0
0
0
90
90
30


Foxtail, Giant
80
80
80
0
0
80
80
70
70
90
90
80



Galium

40
30
70
0
0
60
20
10
0
70
60
0



Kochia

30
0
70
0
0
30
0
0
0
60
60
0


Pigweed
0
0
60
0
0
40
0
0
0
50
20
0


Ragweed
0
0
0
0
0
0
0
0
0
30
30
30


Ryegrass, Italian
0
40
0
0
0
30
20
0
30
80
70
20


Wheat
30
40
30
0
0
20
0
0
0
70
70
20











500 g ai/ha
Compounds





















Postemergence
467
468
469
470
471
472
473
474
475
476
477
478
479
480





Barnyardgrass
90
30
80
70
70
90
90
90
90
90
70
60
50
30


Blackgrass
0
20
40
50
0
60
60
50
40
50
30
20
40
0


Corn
20
0
0
0
0
80
40
20
60
30
40
0
0
0


Foxtail, Giant
80
0
60
80
70
90
90
90
90
80
70
60
60
50



Galium

0
30
0
0
0
50
60
50
60
60
0
0
0
0



Kochia

0
20
0
0
0
70
80
60
60
60
0
0
0
0


Pigweed
0
0
0
0
0
60
90
30
70
40
0
0
0
0


Ragweed
20
0
0
0
0
0
50
0
30
0
0
0
0
0


Ryegrass, Italian
40
0
20
20
0
60
40
50
30
40
0
20
0
0


Wheat
30
20
0
0
0
60
40
30
30
30
40
20
40
30











500 g ai/ha
Compounds





















Postemergence
481
482
483
484
485
486
487
488
489
490
491
492
493
494





Barnyardgrass
20
20
60
50
50
40
90
90
90
80
80
90
90
80


Blackgrass
0
0
0
0
0
0
30
70
70
40
50
70
50
0


Corn
0
0
0
0
20
0
20
80
80
80
90
80
70
0


Foxtail, Giant
20
20
70
40
70
50
90
90
90
80
80
90
90
60



Galium

0
0
0
0
30
20
0
50
40
40
30
60
40
0



Kochia

0
0
20
0
30
0
30
60
40
20
20
60
20
0


Pigweed
0
0
0
0
40
40
20
50
20
20
20
60
0
0


Ragweed
0
0
0
0
0
0
0
20
30
20
20
70
20
0


Ryegrass, Italian
0
0
0
0
0
0
20
60
50
30
30
50
50
0


Wheat
20
0
0
0
20
0
20
60
70
50
60
60
30
0











500 g ai/ha
Compounds





















Postemergence
495
496
497
498
499
500
501
502
503
504
505
506
507
508





Barnyardgrass
80
80
80
70
80
50
80
60
90
90
0
90
60
90


Blackgrass
20
0
30
0
0
0
40
20
70
60
0
60
0
0


Corn
30
0
40
0
0
20
30
30
80
70
0
60
0
20


Foxtail, Giant
70
50
50
40
30
50
80
50
90
90
0
80
20
40



Galium

0
30
50
0
40
0
0
50
70
70
0
50
20
20



Kochia

30
0
30
0
0
20
0
20
0
60
0
0
70
20


Pigweed
0
0
0
0
0
0
0
0
0
70
10
20
0
20


Ragweed
0
0
0
0
0
40
0
0
30
40
0
0
20
0


Ryegrass, Italian
20
0
20
0
0
0
20
30
70
40
0
40
0
0


Wheat
20
0
40
0
0
20
0
0
40
60
0
30
0
20











500 g ai/ha
Compounds





















Postemergence
509
510
513
514
515
516
517
518
519
520
521
522
523
524





Barnyardgrass
90
70
90
90
20
70
30
50
90
90
90
80
90
70


Blackgrass
20
40
40
50
0
0
0
0
50
70
40
50
70
20


Corn
0
0
60
80
0
0
0
0
80
70
40
20
80
0


Foxtail, Giant
40
30
80
90
0
70
0
70
90
80
90
90
90
70



Galium

40
0
40
50
0
0
0
20
50
60
60
60
60
0



Kochia

20
40
50
50
0
0
0
0
20
70
20
50
50
0


Pigweed
0
0
60
30
0
0
0
0
0
50
50
40
60
0


Ragweed
0
30
20
20
0
0
0
0
0
30
0
0
50
0


Ryegrass, Italian
0
20
30
40
0
0
0
0
60
80
40
40
70
0


Wheat
0
0
30
40
0
0
0
0
50
70
50
20
70
0











500 g ai/ha
Compounds



















Postemergence
525
526
527
534
535
536
537
538
539
540
541
544





Barnyardgrass
40
20
20
0
0
0
0
0
90
70
90
70


Blackgrass
30
0
0
0
0
0
0
0
80
60
60
0


Corn
0
0
0
0
0
0
0
0
90
60
60
20


Foxtail, Giant
60
40
20
0
0
30
0
0
90
90
90
60



Galium

0
0
0
0
0
0
0
0
70
70
50
0



Kochia

0
0
0
0
0
0
0
0
70
0
30
0


Pigweed
0
0
0
0
0
0
0
0
50
0
0
0


Ragweed
0
0
0
0
0
0
0
0
50
20
30
0


Ryegrass, Italian
0
0
0
0
0
0
0
0
70
30
40
0


Wheat
0
0
0
0
0
0
0
0
70
60
80
0











500 g ai/ha
Compounds




















Postemergence
545
546
547
549
550
551
552
553
554
557
558
559
560





Barnyardgrass
80
90
90
90
90
80
90
90
90
0
100
100
100


Blackgrass
0
20
0
20
50
0
70
60
70
0
60
60
50


Corn
0
20
0
0
20
0
50
90
70
0
20
30
30


Foxtail, Giant
70
90
90
90
90
80
80
90
80
0
90
90
90



Galium

0
0
20
0
60
0
60
60
60
0
60
60
60



Kochia

0
0
50
20
50
0
30
50
50
0
70
70
80


Pigweed
0
0
0
0
0
0
0
30
0
0
0
0
20


Ragweed
0
0
30
0
0
0
20
40
30
0
40
0
20


Ryegrass, Italian
0
0
0
0
20
0
50
70
90
0
40
30
60


Wheat
0
0
0
20
30
0
40
60
50
0
40
50
50











500 g ai/ha
Compounds





















Postemergence
561
562
563
564
565
566
567
568
569
570
571
572
573
574





Barnyardgrass
90
90
90
90
90
90
100
100
90
100
100
90
100
90


Blackgrass
70
70
50
70
60
70
80
90
80
80
80
80
70
70


Corn
60
80
50
80
20
40
90
90
60
80
80
80
90
80


Foxtail, Giant
90
90
90
90
90
90
90
90
90
90
90
90
90
80



Galium

60
70
70
70
60
80
50
60
60
60
70
60
70
50



Kochia

80
80
80
80
60
80
50
70
50
70
60
60
60
60


Pigweed
70
80
40
70
60
60
20
60
50
20
30
40
40
40


Ragweed
40
60
50
60
50
40
0
30
60
0
0
20
60
0


Ryegrass, Italian
60
80
40
70
30
60
70
90
60
80
60
60
90
70


Wheat
70
80
40
60
40
40
60
70
70
60
70
70
70
70











500 g ai/ha
Compounds





















Postemergence
575
576
577
587
588
589
590
591
592
593
594
595
596
597





Barnyardgrass
90
90
100
90
80
80
90
90
90
90
90
90
90
30


Blackgrass
80
50
80
60
50
40
70
60
60
60
60
40
50
20


Corn
80
80
80
70
70
60
70
80
70
70
70
60
60
20


Foxtail, Giant
90
90
90
90
80
80
90
90
90
90
90
90
90
30



Galium

70
60
50
0
30
0
30
50
30
20
20
20
50
20



Kochia

20
60
40
20
70
0
30
60
40
0
40
30
60
0


Pigweed
20
50
0
0
40
0
0
70
0
0
40
30
20
0


Ragweed
0
50
30
0
50
0
0
30
0
0
50
0
0
0


Ryegrass, Italian
70
60
30
30
50
40
30
70
0
30
30
40
40
0


Wheat
70
70
70
60
40
50
70
60
70
40
70
50
50
20











500 g ai/ha
Compounds



















Postemergence
598
599
600
601
602
605
606
607
608
609
610
611





Barnyardgrass
80
20
90
70
0
80
70
60
40
80
90
90


Blackgrass
0
0
0
0
0
20
40
0
40
40
70
70


Corn
0
0
0
20
0
0
0
0
20
30
50
70


Foxtail, Giant
20
0
30
50
0
80
90
60
70
90
90
90



Galium

30
0
0
0
0
0
70
0
50
40
60
60



Kochia

20
0
0
0
0
0
0
0
60
60
60
70


Pigweed
0
0
0
0
0
0
70
0
30
30
50
30


Ragweed
20
0
0
0
0
0
0
0
20
0
30
30


Ryegrass, Italian
0
0
0
0
0
0
0
0
30
40
40
70


Wheat
0
0
0
20
0
30
0
20
0
20
20
60











500 g ai/ha
Compounds




















Postemergence
612
613
614
616
617
618
619
620
621
622
623
624
625





Barnyardgrass
90
90
90
90
90
90
0
60
90
90
90
90
90


Blackgrass
60
60
70
60
60
60
0
0
20
60
60
50
40


Corn
90
80
20
80
80
80
0
0
20
70
70
40
50


Foxtail, Giant
90
90
90
90
90
90
0
50
90
90
90
90
90



Galium

50
60
40
70
60
60
0
20
40
70
60
50
60



Kochia

40
70
50
70
60
60
0
0
20
60
70
60
50


Pigweed
50
70
30
60
50
30
0
0
0
50
60
60
50


Ragweed
20
30
0
20
50
20
0
0
0
40
0
0
20


Ryegrass, Italian
70
60
20
80
50
50
0
0
20
50
60
30
30


Wheat
30
50
40
70
60
70
0
0
50
70
70
70
50











500 g ai/ha
Compounds

















Postemergence
630
631
632
633
634
635
636
637
638
639





Barnyardgrass
90
0
90
90
80
90
90
90
90
90


Blackgrass
20
0
60
50
0
70
60
60
70
60


Corn
20
0
80
60
0
70
80
70
80
80


Foxtail, Giant
30
0
90
90
80
90
90
90
90
90



Galium

40
0
50
50
60
60
50
50
60
50



Kochia

0
0
60
60
0
80
60
30
40
70


Pigweed
0
0
40
0
0
80
50
60
50
50


Ragweed
0
0
30
0
0
40
30
20
0
30


Ryegrass, Italian
0
0
50
50
20
30
70
20
40
50


Wheat
20
0
60
40
0
40
60
70
70
60











500 g ai/ha
Compounds





















Postemergence
640
641
642
643
644
645
646
647
648
649
650
651
652
653





Barnyardgrass
90
90
90
90
90
90
90
90
80
70
90
90
90
90


Blackgrass
50
60
40
60
70
70
80
60
50
60
50
70
70
70


Corn
0
50
70
70
80
60
80
40
0
0
90
90
60
30


Foxtail, Giant
90
90
70
90
90
90
90
90
50
60
90
80
90
90



Galium

50
50
70
50
60
50
50
50
60
70
70
60
50
50



Kochia

40
20
50
20
70
50
70
20
0
60
40
40
0
0


Pigweed
20
20
20
0
30
0
20
0
50
30
0
30
20
0


Ragweed
0
20
40
30
40
20
40
10
30
60
30
20
0
0


Ryegrass, Italian
0
40
50
30
80
50
70
0
50
40
70
70
70
60


Wheat
50
30
20
50
80
50
70
50
0
0
70
60
40
60











500 g ai/ha
Compounds





















Postemergence
654
655
656
657
658
659
660
661
662
663
664
665
666
667





Barnyardgrass
90
90
90
90
90
90
80
90
90
90
90
90
90
90


Blackgrass
50
30
30
30
70
50
40
70
80
70
60
70
60
70


Corn
70
30
20
0
30
50
0
90
90
80
90
70
80
80


Foxtail, Giant
90
60
60
60
60
90
90
90
90
90
90
90
90
90



Galium

60
50
60
30
60
20
0
60
70
60
60
50
40
50



Kochia

50
40
30
0
30
20
0
70
70
60
70
50
30
60


Pigweed
20
0
0
0
0
0
0
0
50
20
20
20
0
0


Ragweed
20
0
0
0
40
0
0
50
60
40
20
30
0
50


Ryegrass, Italian
60
30
0
0
60
60
0
80
70
70
70
80
60
80


Wheat
40
10
20
0
30
50
0
80
80
70
70
70
60
70













500 g ai/ha
Compounds


















Postemergence
668
674
675
676
677
678
679
680
681







Barnyardgrass
90
70
70
80
90
80
70
60
90



Blackgrass
70
0
20
40
20
60
60
20
30



Corn
80
0
0
50
40
30
50
20
30



Foxtail, Giant
90
80
80
80
70
60
30
30
30




Galium

70
0
0
40
40
30
60
20
50




Kochia

20
0
0
0
40
0
0
0
40



Pigweed
0
0
0
0
20
0
40
0
0



Ragweed
0
0
0
0
30
0
20
0
0



Ryegrass, Italian
70
0
0
20
30
20
20
0
20



Wheat
60
0
0
20
20
20
20
0
0












500 g ai/ha
Compounds





















Postemergence
682
683
684
685
686
687
688
689
690
691
692
693
694
695





Barnyardgrass
20
20
70
70
90
90
90
90
80
80
80
80
70
90


Blackgrass
0
20
20
20
40
40
60
60
70
60
60
50
30
40


Corn
0
20
20
0
50
70
70
80
80
90
50
70
0
80


Foxtail, Giant
80
80
80
80
90
90
90
90
80
80
80
80
80
80



Galium

0
0
0
0
20
20
50
50
70
70
60
70
0
40



Kochia

0
0
0
0
30
30
60
60
70
80
60
70
0
50


Pigweed
0
0
0
0
20
20
50
60
70
70
50
70
50
30


Ragweed
0
0
0
0
20
30
50
50
70
60
30
10
0
40


Ryegrass, Italian
0
0
0
0
40
40
60
60
60
60
60
70
50
20


Wheat
20
20
20
20
30
60
70
60
60
60
50
50
0
40











500 g ai/ha
Compounds


















Postemergence
696
697
698
699
700
701
702
703
704
705
706





Barnyardgrass
80
90
80
80
70
70
70
70
90
0
50


Blackgrass
40
40
40
60
50
0
0
0
30
0
0


Corn
70
80
80
60
70
0
0
0
0
0
0


Foxtail, Giant
80
80
80
80
90
70
80
90
90
0
30



Galium

70
50
50
60
60
0
40
0
40
0
0



Kochia

40
60
60
50
60
0
0
0
20
0
0


Pigweed
60
50
60
20
30
0
0
0
20
0
0


Ragweed
40
50
40
30
30
0
0
0
20
0
0


Ryegrass, Italian
40
30
30
30
40
0
0
0
20
0
0


Wheat
50
40
40
20
60
0
0
0
0
0
0













500 g ai/ha
Compounds














Postemergence
711
712
714
715
716







Barnyardgrass
0
0
0
0
0



Blackgrass
0
0






Corn
0
0
0
0
0



Crabgrass, Large


0
0
0



Foxtail, Giant
0
0
0
0
0




Galium

0
0







Kochia

0
0






Morningglory


0
0
0



Pigweed
0
0
0
0
0



Ragweed
0
0






Ryegrass, Italian
0
0






Velvetleaf


0
0
0



Wheat
0
0
0
0
0

























500 g ai/ha
















Postemergence
1000
1001
1002
1013
1014
1015
1016
1017
1018
1019
1020
1021
1022
1023





Barnyardgrass
100 
0
90 
90
90
90
90 
90
90
0
90
100 
100 
90


Blackgrass
0
0
0
40
50
50
0
40
50
0
20
50
 0
20


Corn
20 
0
0
90
90
90
0
90
90
0
30
80
20
50


Crabgrass, Large
















Foxtail, Giant
50 
0
50 
90
90
80
80 
90
90
0
90
90
70
90



Galium

0
0
0
70
60
70
0
70
60
0
60
70
50
60



Kochia

40 
0
40 
60
50
50
0
60
50
0
50
70
60
50


Morningglory
















Pigweed
0
0
0
40
30
50
0
40
60
0
30
50
 0
30


Ragweed
0
0
0
40
30
40
0
40
30
0
 0
60
 0
 0


Ryegrass, Italian
0
0
0
60
60
50
0
50
60
0
30
70
30
30


Velvetleaf
















Wheat
0
0
0
60
80
60
0
60
50
0
30
60
30
20











500 g ai/ha
Compounds





















Postemergence
1024
1025
1026
1027
1028
1029
1030
1031
1032
1033
1034
1035
1036
1037





Barnyardgrass
90
70
90
90
90
90
90
0
0
90
90
90
90
90


Blackgrass
20
 0
 0
40
40
40
60
0
0
40
30
60
 0
20


Corn
70
20
30
 0
30
70
50
0
0
40
50
60
20
30


Crabgrass, Large
















Foxtail, Giant
90
60
20
60
80
90
90
0
0
80
80
90
60
30



Galium

60
30
50
70
50
40
60
0
0
60
60
50
30
60



Kochia

60
50
 0
30
 0
 0
 0
0
0
 0
30
20
 0
20


Morningglory
















Pigweed
50
30
 0
 0
 0
 0
 0
0
0
 0
 0
 0
 0
 0


Ragweed
 0
 0
 0
 0
 0
 0
 0
0
0
30
40
 0
10
30


Ryegrass, Italian
30
30
 0
30
40
40
 0
0
0
20
60
60
60
50


Velvetleaf
















Wheat
30
 0
30
 0
40
60
60
0
0
 0
50
70
20
30











500 g ai/ha
Compounds





















Postemergence
1038
1039
1040
1041
1042
1043
1044
1045
1046
1047
1048
1049
1053
1054





Barnyardgrass
90
90
90
50
90
80
80
90
90
80 
80
50
0
0


Blackgrass
50
40
70
40
70
30

60
50
0
30
 0
0
0


Corn
80
70
80
30
70
60
50
40
60
0
40
 0
0
0


Crabgrass, Large
















Foxtail, Giant
90
90
90
50
90
80
90
90
90
80 
80
80
0
0



Galium

70
60
70
60
50
40
60
50
50
50 
60
40
0
0



Kochia

80
60
70

60
40
50
 0
 0
20 
60
30
0
0


Morningglory
















Pigweed
20
20
60
20
40
30
30
 0
20
0
60
50
0
0


Ragweed
30
40
40

30
10
40
30
 0
0
50
40
0
0


Ryegrass, Italian
50
60
60
20
50
20
30
50
60
0
40
 0
0
0


Velvetleaf
















Wheat
60
60
30
30
30
 0
20
40
30
0
20
 0
0
0











500 g ai/ha
Compounds





















Postemergence
1055
1056
1057
1058
1059
1073
1094
1095
1096
1097
1098
1099
1100
1101





Barnyardgrass
0
50 
0
90
90 
90
80
0
0
0
90
80
70
80


Blackgrass
0
0
0
40
0
30
30
0
0
0
30
40
20
30


Corn
0
0
0
30
20 
50
 0
0
0
0
70
60
20
70


Crabgrass, Large
















Foxtail, Giant
0
20 
0
 0
40 
40
80
0
0
0
90
80
70
80



Galium

0
0
0
60
0

20
0
0
0
40
60
20
60



Kochia

0
0
0
20
0
40
 0
0
0
0
60
60
20
60


Morningglory
















Pigweed
0
0
0
 0
0
20
20
0
0
0
 0
50
 0
50


Ragweed
0
0
0
90
0
30
 0
0
0
0
 0
40
 0
 0


Ryegrass, Italian
0
0
0
 0
20 
40
20
0
0
0
50
60
20
60


Velvetleaf
















Wheat
0
0
0
 0
0
30
30
0
0
0
50
50
20
50











500 g ai/ha
Compounds





















Postemergence
1102
1111
1112
1113
1114
1115
1116
1117
1118
1119
1120
1121
1122
1123





Barnyardgrass
80
0
0
0
90
90
60
90
90
90
90
90
90
90


Blackgrass
50
0
0
0
60
40
30
40
60
70
50
60
60
80


Corn
60
0
0
0
70
50
 0
40
20
30
60
90
90
80


Crabgrass, Large
















Foxtail, Giant
90
50 
0
0
90
90
 0
70
50
70
90
90
90
90



Galium

30
0
0
0
20
30
40
40
60
50
60
60
60
50



Kochia

 0
0
0
0
20
40
30
40
30
60
70
70
60
70


Morningglory
















Pigweed
 0
0
0
0
 0
20
 0
 0
20
20
20
40
40
20


Ragweed
20
0
0
0
 0
30
 0
30
20
60
50
40
50
50


Ryegrass, Italian
30
0
0
0
40
40
20
40
50
30
40
70
60
50


Velvetleaf
















Wheat
50
0
0
0
30
30
20
70
20
50
50
60
70
60











500 g ai/ha
Compounds





















Postemergence
1124
1125
1126
1127
1128
1129
1130
1131
1132
1133
1134
1135
1136
1137





Barnyardgrass
90
90
90
40 
90
90 
20 
90
90
90
80
0
90 
0


Blackgrass
 0
50
40
20 
50
0
0
60
50
70
50
0
30 
0


Corn
 0
60
90
0
50
0
0
80
80
80
20
0
0
0


Crabgrass, Large
















Foxtail, Giant
90
90
90
50 
90
90 
30 
90
90
90
80
0
90 
0



Galium

60
50
40
40 
70
0
0
60
30
70
70
0
20 
0



Kochia

70
40
70
0
70
0
0
70
 0
70
30
0
0
0


Morningglory
















Pigweed
60
 0
30
0
 0
0
0
80
 0
70
20
0
0
0


Ragweed
50
 0
40
0
50
0
0
80
 0
70
30
0
0
0


Ryegrass, Italian
 0
60
50
0
30
0
0
50
30
40
20
0
0
0


Velvetleaf
















Wheat
 0
40
70
0
 0
0
0
70
70
70
20
0
0
0











500 g ai/ha
Compounds





















Postemergence
1138
1139
1140
1151
1152
1153
1154
1155
1156
1157
1158
1159
1160
1177





Barnyardgrass
90
90
90
90
0
90 
90
90
90
90
90
90
90
90


Blackgrass
60
60
70
60
0
30 
90
 0
40
50
40
 0
50
70


Corn
80
80
70
80
0
0
90
30
60
50
60
20
80
40


Crabgrass, Large
















Foxtail, Giant
90
70
90
80
40 
90 
60
70
90
90
80
70
90
70



Galium

50
60
50
60
20 
40 
70
60
50
60
30
20
60
50



Kochia

 0
 0
40
60
0
0
60
 0
20
50
 0
 0
20
 0


Morningglory
















Pigweed
 0
 0
 0
80
0
0
70
 0
 0
 0
 0
20
 0
 0


Ragweed
 0
40
30
30
0
0
40
40
 0
50
 0
 0
 0
 0


Ryegrass, Italian
50
50
70
50
0
0
50
20
30
40
50
 0
20
40


Velvetleaf
















Wheat
70
70
70
60
0
0
80
50
50
70
50
 0
50
30











500 g ai/ha
Compounds





















Postemergence
1178
1179
1180
1181
1182
1194
1195
1196
1197
1198
1199
1200
1201
1202





Barnyardgrass
30
0
0
0
0
20 
20 
90 

90
100 
0
100 



Blackgrass
20
0
0
0
0
0
0
0
50
60
 0
0
 0
40


Corn
 0
0
0
0
0
0
0
0
90
20
 0
0
 0
30


Crabgrass, Large
















Foxtail, Giant
30
0
0
0
0
20 
20 
80 
90
90
90
0
90
90



Galium

30
0
0
0
0
0
0
0
60
50
40
0
50
40



Kochia

40

0

0
0
0
0
80
60
40
0
70
40


Morningglory
















Pigweed
 0
0
0
0
0
0
0
0
70
70
20
0
60
20


Ragweed
20
0
0
0
0
0
0
0
60
30
 0
0
30
20


Ryegrass, Italian
 0
0
0
0
0
0
0
0
60
30
20
0
 0
 0


Velvetleaf
















Wheat
 0
0
0
0
0
0
0
0
60
60
 0
0
 0
50











500 g ai/ha
Compounds





















Postemergence
1203
1204
1205
1206
1207
1208
1209
1210
1211
1212
1213
1214
1215
1216





Barnyardgrass


50
100 
100 
100 


100 
100 
100 
90




Blackgrass
60
70
20
0
 0
 0
30
50
40
30
40
80
0
0


Corn
70
80
80
0
 0
50
 0
50
90
20
80
90
0
0


Crabgrass, Large
















Foxtail, Giant
90
90
80
80 
90
90
90
90
80
90
90
90
90 
80 



Galium

60
60
40
50 
40
50
30
 0
60
60
60
60
0
0



Kochia

60
80
 0
50 
60
70
50
 0
30
80
60
80
30 
40 


Morningglory
















Pigweed
20
80
 0
30 
20
60
 0
 0
30
70
 0
60
0
0


Ragweed
30
60
 0
0
30
40
 0
 0
 0
30
 0
30
0
0


Ryegrass, Italian
 0
80
30
0
 0
 0
20
60
70
20
50
80
0
0


Velvetleaf
















Wheat
50
70
40
0
 0
20
20
60
60
40
50
80
0
0











500 g ai/ha
Compounds





















Postemergence
1217
1218
1219
1220
1221
1222
1223
1224
1225
1226
1227
1228
1229
1230





Barnyardgrass


60 
80
60
0
50
90 
90
100 
70 
90
100 
70 


Blackgrass
0
0
0
40
70
0
50
0
40
30
0
40
40
0


Corn
0
0
0
70
60
0
 0
0
90
70
0
70
 0
0


Crabgrass, Large
















Foxtail, Giant
90 
50 
80 
80
90
70 
90
70 
90
80
0
80
90
80 



Galium

0
0
0
40
60
0
40
40 
70
80
0
60
50
60 



Kochia

0
20 





0

60
30 
60
80
70 


Morningglory
















Pigweed
0
0
0
20
 0
0
 0
20 
40
60
30 
50
60
60 


Ragweed
0
0
20 
30
20
0
20
0
50
50
0
 0
 0
0


Ryegrass, Italian
0
0
20 
30
70
0
60
0
30
 0
0
30
40
0


Velvetleaf
















Wheat
0
0
0
40
60
0
30
0
70
 0
0
30
50
0











500 g ai/ha
Compounds





















Postemergence
1231
1232
1233
1234
1235
1236
1238
1239
1240
1241
1242
1243
1244
1245





Barnyardgrass
80
80
80
90
100 
100 
80
80
0
30 
40 
0
80
90


Blackgrass
40
40
40
60
40
30
50
80
0
0
0
0
50
60


Corn
80
70
80
100 
100 
90
40
70
0
20 
0
0
40
 0


Crabgrass, Large
















Foxtail, Giant
90
90
90
90
90
90
80
90
0
20 
50 
0
90
60



Galium

70
60
60
60
70
60
50
60
0
0
20 
0
20
50



Kochia




50
50
30
50
70
0
0
0
0
 0
40


Morningglory
















Pigweed
50
40
20
50
50
40
30
50
0
0
0
0
 0
 0


Ragweed
30
50
30
30
30
40
20
60
0
0
0
0
 0
50


Ryegrass, Italian
50
60
50
70
30
50
60
50
0
0
0
0
30
 0


Velvetleaf
















Wheat
70
40
70
50
70
20
30
60
0
0
0
20
40
20











500 g ai/ha
Compounds





















Postemergence
1246
1247
1248
1249
1250
1251
1252
1253
1254
1255
1256
1257
1260
1280





Barnyardgrass
80
70 
50 
100 
90
100 
90
100 
90
100 
90
0
90
40 


Blackgrass
40
0
0
50
60
40
50
50
40
60
20
0
80
0


Corn
40
0
0
90
70
80
90
70
50
90
50
0
90
0


Crabgrass, Large
















Foxtail, Giant
20
30 
20 
80
80
80
80
90
80
80
80
0
90
30 



Galium

60
20 
0
50
60
50
60
60
50
60
50
0
70
0



Kochia

20
0
0
70
20
70
60
70
40
50
70
0
70
0


Morningglory
















Pigweed
20
0
0
80
30
80
50
30
20
30
50
0
70
0


Ragweed
60
0
0
60
 0
50
50
 0
 0
40
20
0
70
0


Ryegrass, Italian
 0
0
0
70
50
40
70
60
70
40
70
0
80
0


Velvetleaf
















Wheat
40
0
0
70
70
60
70
50
40
60
50
0
90
0











500 g ai/ha
Compounds





















Postemergence
1281
1298
1299
1300
1301
1302
1303
1304
1305
1306
1307
1308
1309
1310





Barnyardgrass
80 
80 
90
90
90 
90
30 
0
80 
90 
90 
80
90
90


Blackgrass
0
0
60
50
0
20
0
0
0
0
0
50
60
40


Corn
0
0
80
60
0
 0
0
0
0
0
0
80
20
50


Crabgrass, Large
















Foxtail, Giant
30 
90 
90
90
20 
80
60 
0
90 
20 
20 
80
70
90



Galium

50 
20 
50
40
60 
30
0
0
0
40 
40 
50
50
60



Kochia

30 
0
60
 0
50 
20

0
0
60 
40 
 0
50
50


Morningglory
















Pigweed
0
0
 0
 0
0
 0
0
0
0
0
0
 0
 0
30


Ragweed
0
0
20
 0
0
 0
0
0
0
0
0
20
30
40


Ryegrass, Italian
0
0
60
30
0
20
0
0
0
0
0
 0
20
40


Velvetleaf
















Wheat
0
20 
40
50
0
 0
0
0
20 
0
0
40
20
60











500 g ai/ha
Compounds





















Postemergence
1311
1312
1313
1314
1316
1317
1318
1319
1320
1321
1323
1324
1325
1326





Barnyardgrass




90
90
90
90
50 
90
90
90
90
90 


Blackgrass
60
70
0
60
80
80
70
80
0
50
60
60

0


Corn
80
90
0
70
80
80
80
80
0
70
70
80
50
0


Crabgrass, Large
















Foxtail, Giant
90
90
90 
90
90
90
90
90
20 
90
90
90
90
0



Galium

60
60
40 
50
60
60
60
60
40 
50
60
50
90
20 



Kochia

50
70
50 
60
40
30
40
60
0
50
70
70
80
0


Morningglory
















Pigweed
20
40
0
30
60
20
40
50
0
 0
 0
20
90
0


Ragweed
30
70
0
50
70
20
60
 0
0
20
50
40
 0
0


Ryegrass, Italian
80
50
0
 0
80
80
40
60
0
50
70
50
 0
20 


Velvetleaf
















Wheat
80
80
0
60
80
60
80
60
0
50
70
70
 0
0











500 g ai/ha
Compounds





















Postemergence
1327
1328
1329
1330
1331
1332
1334
1335
1336
1355
1356
1357
1358
1359





Barnyardgrass
90
90 
90
90
90 
60
50
0
0
0
0
0
0
0


Blackgrass
20
0
60
70
50 
30
 0
0
0







Corn
 0
0
50
 0
70 
 0
30
0
0
0
0
0
0
0


Crabgrass, Large









0
0
0
30 
0


Foxtail, Giant
70
40 
90
90
90 
60
50
0
0
0
0
0
0
0



Galium

50
30 
60
30
0
20
50
0
0








Kochia

30
0
50
20
0
 0
 0
0
0







Morningglory









0
0
0
0
0


Pigweed
 0
0
 0
 0
0
 0
40
0
0
0
0
0
0
0


Ragweed
20
0
 0
20
0
20
20
0
0







Ryegrass, Italian
40
30 
50
20
0
 0
20
0
0







Velvetleaf









0
0
0
0
0


Wheat
 0
0
20
70
50 
20
 0
0
0
0
0
0
0
0











500 g ai/ha
Compounds





















Postemergence
1360
1361
1362
1370
1371
1372
1373
1374
1376
1377
1378
1379
1380
1381





Barnyardgrass
0
0
0

90


50 
90
90
80
100 
80
80


Blackgrass



80
60
70
60
0
70
60
40
30
60
60


Corn
0
0
0
80
90
90
90
0
30
80
80
70
80
60


Crabgrass, Large
0
0
0













Foxtail, Giant
0
0
0
90
90
90
90
0
80
80
90
80
90
90



Galium




50
70
70
60
0
30
60
70
60
50
60



Kochia




50
80
80
80
0
20
70

60




Morningglory
0
0
0













Pigweed
0
0
0
30
60
80
90
0
20
40
70
50
60
70


Ragweed



30
60
60
70
0
 0
60
70
60
50
60


Ryegrass, Italian



70
50
30
50
0
30
60
60
30
60
60


Velvetleaf
0
0
0













Wheat
0
0
0
70
60
90
60
0
60
60
70
50
40
50











500 g ai/ha
Compounds




















Postemergence
1382
1383
1384
1385
1386
1387
1388
1389
1390
1391
1392
1394
1395





Barnyardgrass
80 
100 
90
90
90
80
100 
100 
90
100 
40 
90
90 


Blackgrass
0
50
30
20
80
40
90
50
60
70
0
60
0


Corn
0
90
90
20
80
10
80
90
70
80
20 
70
70 


Crabgrass, Large















Foxtail, Giant
70 
90
90
90
90
80
90
80
90
90
30 
90
90 



Galium

30 
60
70
50
60
50
50
70
60
70
0
60
0



Kochia

0
70
60
 0
70
50
50
80
70
80
0
 0
0


Morningglory















Pigweed
0
70
20
 0
70
60
50
70
80
90
0
20
0


Ragweed
0
60
40
 0
50
30
50
20
30
60
0
20
0


Ryegrass, Italian
0
50
30
20
60
40
90
80
50
60
0
20
20 


Velvetleaf















Wheat
0
80
50
20
60
 0
60
70
50
60
30 
60
40 











125 g ai/ha
Compounds




















Postemergence
352
353
354
356
360
361
362
363
364
365
366
367
368





Barnyardgrass
0
0
0
0
0
0
0
0
0
0
0
0
90 


Blackgrass












0


Corn
0
0
0
0
0
0
0
0
0
0
0
0
0


Crabgrass, Large
0
0
0
0
0
0
0
0
0
0
0
0



Foxtail, Giant
0
0
0
0
0
0
0
0
0
0
0
0
20 



Galium













30 



Kochia













0


Morningglory
0
0
0
0
0
0
0
0
0
0
0
0



Pigweed
0
0
0
0
0
0
0
0
0
0
0
0
0


Ragweed












0


Ryegrass, Italian












20 


Velvetleaf
0
0
0
0
0
0
0
0

0
0
0



Wheat
0
0
0
0
0
0
0
0
0
0
0
0
0











125 g ai/ha
Compounds





















Postemergence
369
370
371
372
373
374
375
376
377
378
379
380
381
382





Barnyardgrass
90
80
80
80
80
80
90
90
90
80
0
50
0
0


Blackgrass
30
0
30
20
20
0
50
0
50
50
0
30
0
0


Corn
0
0
20
0
20
0
30
0
0
50
0
0
0
0


Foxtail, Giant
20
40
50
50
40
20
90
90
80
80
0
30
0
0



Galium

60
20
30
0
30
0
40
30
60
60
0
20
0
0



Kochia

20
0
20
0
0
0
30
0
30
50
0
0
0
0


Pigweed
0
0
0
20
20
0
20
0
0
0
0
0
0
0


Ragweed
0
0
0
0
0
0
0
0
40
20
0
0
0
0


Ryegrass, Italian
20
0
20
20
30
0
0
0
30
40
0
0
0
0


Wheat
0
0
0
0
20
0
30
0
0
40
0
0
0
0











125 g ai/ha
Compounds




















Postemergence
383
384
386
387
388
389
390
391
392
393
394
395
396





Barnyardgrass
70
0
70
70
30
50
50
60
80
80
40
0
70


Blackgrass
0
0
50
0
10
0
0
50
70
60
0
0
50


Corn
0
0
40
0
0
30
0
40
70
80
0
0
70


Foxtail, Giant
30
0
70
50
50
60
60
90
90
90
0
0
80



Galium

0
0
50
0
0
0
0
60
70
70
0
0
60



Kochia

0
0
0
0
0
0
0
0
50
60
0
0
60


Pigweed
0
0
0
0
0
0
0
30
60
50
0
0
60


Ragweed
0
0
0
0
0
0
0
20
50
0
0
0
0


Ryegrass, Italian
20
0
20
0
0
0
0
30
50
40
0
0
50


Wheat
0
0
30
0
0
0
0
0
20
20
0
0
20











125 g ai/ha
Compounds





















Postemergence
397
398
399
400
401
402
403
404
405
406
407
408
409
410





Barnyardgrass
70
90
90
90
90
90
90
90
90
90
60
0
60
20


Blackgrass
60
40
40
60
0
50
50
40
50
30
30
0
10
0


Corn
50
60
50
20
0
70
70
40
30
20
0
0
0
0


Foxtail, Giant
70
80
90
50
30
90
90
90
80
80
70
0
60
0



Galium

60
50
50
40
50
50
50
50
60
50
0
0
0
0



Kochia

20
60
50
60
50
20
40
60
40
40
0
0
0
0


Pigweed
40
50
30
30
0
40
50
20
40
20
0
0
0
0


Ragweed
0
0
0
40
30
20
0
30
0
20
0
0
0
0


Ryegrass, Italian
40
20
40
20
30
30
50
40
30
30
0
0
0
0


Wheat
40
20
40
30
20
50
70
50
60
40
0
0
0
0











125 g ai/ha
Compounds





















Postemergence
411
412
413
414
415
416
417
418
419
420
421
422
423
424





Barnyardgrass
40
0
0
0
0
0
0
0
60
80
70
50
0
50


Blackgrass
0
0
0
0
0
0
0
0
0
0
20
30
0
0


Corn
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Foxtail, Giant
40
0
0
0
0
0
0
0
20
70
80
50
0
40



Galium

30
0
0
0
0
0
0
0
0
0
50
30
0
0



Kochia

0
0
0
0
0
0
0
0
20
0
0
50
0
0


Pigweed
0
0
0
0
0
0
0
0
0
0
0
40
0
0


Ragweed
0
0
0
0
0
0
0
0
0
0
20
0
0
0


Ryegrass, Italian
0
0
0
0
0
0
0
0
0
0
20
0
0
0


Wheat
0
0
0
0
0
0
0
0
0
0
0
0
0
0











125 g ai/ha
Compounds





















Postemergence
425
426
427
428
429
430
431
432
433
434
435
436
437
438





Barnyardgrass
20
30
60
90
90
80
80
20
90
90
80
90
90
90


Blackgrass
0
0
20
40
50
20
60
0
30
50
30
30
0
40


Corn
0
0
0
30
70
50
60
0
0
0
0
0
0
0


Foxtail, Giant
20
20
50
80
90
80
80
40
80
90
80
80
90
90



Galium

0
0
40
50
70
50
60
0
50
60
50
60
30
40



Kochia

0
0
0
30
60
20
40
0
40
70
20
40
20
70


Pigweed
0
0
0
0
70
30
50
0
20
60
20
20
0
0


Ragweed
0
0
0
0
30
0
20
0
0
20
40
0
0
0


Ryegrass, Italian
0
0
0
30
60
30
60
0
30
0
40
20
0
40


Wheat
0
0
0
30
50
20
40
0
30
20
0
20
0
30











125 g ai/ha
Compounds





















Postemergence
439
440
441
442
443
444
445
446
447
448
449
450
451
452





Barnyardgrass
90
90
80
80
80
80
90
80
80
80
30
80
0
20


Blackgrass
0
30
50
60
60
70
40
50
0
0
0
20
0
0


Corn
0
0
60
50
40
60
70
20
0
0
0
20
0
0


Foxtail, Giant
90
90
80
80
80
80
90
90
80
60
30
80
0
60



Galium

40
40
50
60
40
60
60
50
40
30
0
50
0
50



Kochia

30
30
40
20
20
40
20
60
0
30
20
20
0
50


Pigweed
40
0
40
60
20
50
20
50
0
20
0
50
0
50


Ragweed
0
0
20
0
20
20
20
0
0
0
0
20
0
0


Ryegrass, Italian
0
0
60
60
30
50
40
20
0
0
0
0
0
0


Wheat
0
0
50
40
40
50
30
0
0
0
0
0
0
0











125 g ai/ha
Compounds



















Postemergence
453
454
455
456
457
460
461
462
463
464
465
466





Barnyardgrass
80
60
70
0
0
60
80
70
50
90
90
80


Blackgrass
0
0
0
0
0
20
0
20
20
60
40
30


Corn
0
50
0
0
0
20
0
0
0
90
80
0


Foxtail, Giant
80
70
70
0
0
90
80
60
70
90
90
20



Galium

30
0
30
0
0
50
0
0
0
60
60
0



Kochia

20
0
60
0
0
0
0
0
0
50
50
0


Pigweed
0
0
50
0
0
20
0
0
0
40
0
0


Ragweed
0
0
0
0
0
0
0
0
0
30
0
0


Ryegrass, Italian
0
0
0
0
0
30
0
0
0
70
60
0


Wheat
0
20
0
0
0
0
0
0
0
70
60
0











125 g ai/ha
Compounds





















Postemergence
467
468
469
470
471
472
473
474
475
476
477
478
479
480





Barnyardgrass
80
0
70
60
50
90
90
90
90
90
40
30
0
0


Blackgrass
0
0
0
30
0
30
40
30
30
20
0
0
0
0


Corn
0
0
0
0
0
40
0
0
0
0
0
0
0
0


Foxtail, Giant
40
0
20
40
50
80
70
90
90
80
40
20
0
20



Galium

0
20
0
0
0
50
60
40
50
30
0
0
0
0



Kochia

0
0
0
0
0
60
40
50
40
30
0
0
0
0


Pigweed
0
0
0
0
0
60
50
30
50
20
0
0
0
0


Ragweed
0
0
0
0
0
0
50
0
20
0
0
0
0
0


Ryegrass, Italian
0
0
0
0
0
40
0
20
20
30
0
0
0
0


Wheat
0
0
0
0
0
30
0
0
0
0
0
0
0
0











125 g ai/ha
Compounds





















Postemergence
481
482
483
484
485
486
487
488
489
490
491
492
493
494





Barnyardgrass
0
0
20
0
20
0
80
90
90
80
90
90
90
30


Blackgrass
0
0
0
0
0
0
0
60
50
20
20
50
20
0


Corn
0
0
0
0
0
0
0
70
70
80
60
70
0
0


Foxtail, Giant
0
0
20
0
20
0
80
90
90
80
80
90
90
20



Galium

0
0
0
0
0
0
0
50
0
20
0
50
30
0



Kochia

0
0
0
0
0
0
0
30
0
0
0
40
0
0


Pigweed
0
0
0
0
0
0
0
40
0
0
0
40
0
0


Ragweed
0
0
0
0
0
0
0
20
0
0
0
30
20
0


Ryegrass, Italian
0
0
0
0
0
0
0
30
30
0
0
20
20
0


Wheat
0
0
0
0
0
0
0
50
30
30
30
20
0
0











125 g ai/ha
Compounds





















Postemergence
495
496
497
498
499
500
501
502
503
504
505
506
507
508





Barnyardgrass
20
60
60
30
30
0
50
0
90
80
0
70
20
70


Blackgrass
0
0
30
0
0
0
30
0
30
40
0
30
0
0


Corn
0
0
0
0
0
0
0
0
20
70
0
0
0
0


Foxtail, Giant
20
20
20
20
20
0
70
20
90
90
0
80
0
0



Galium

0
0
0
0
0
0
0
20
30
70
0
40
0
0



Kochia

30
0
30
0
0
0
0
0
0
30
0
0
30
0


Pigweed
0
0
0
0
0
0
0
0
0
60
0
0
0
0


Ragweed
0
0
0
0
0
0
0
0
30
30
0
0
0
0


Ryegrass, Italian
0
0
0
0
0
0
0
0
40
40
0
20
0
0


Wheat
0
0
0
0
0
0
0
0
0
20
0
0
0
0











125 g ai/ha
Compounds





















Postemergence
509
510
513
514
515
516
517
518
519
520
521
522
523
524





Barnyardgrass
60
60
80
80
0
0
20
0
90
90
90
60
90
30


Blackgrass
0
0
20
20
0
0
0
0
50
70
30
30
50
0


Corn
0
0
20
30
0
0
0
0
60
60
30
0
20
0


Foxtail, Giant
0
10
80
70
0
0
0
20
90
80
70
90
80
30



Galium

0
0
0
40
0
0
0
0
30
60
50
30
50
0



Kochia

0
0
20
30
0
0
0
0
0
60
0
20
20
0


Pigweed
0
0
30
0
0
0
0
0
0
40
40
20
30
0


Ragweed
0
0
10
0
0
0
0
0
0
30
0
0
50
0


Ryegrass, Italian
0
0
0
20
0
0
0
0
40
40
20
20
30
0


Wheat
0
0
0
30
0
0
0
0
30
50
20
0
0
0











125 g ai/ha
Compounds



















Postemergence
525
526
527
534
535
536
537
538
539
540
541
544





Barnyardgrass
40
10
0
0
0
0
0
0
90
60
90
20


Blackgrass
0
0
0
0
0
0
0
0
50
50
30
0


Corn
0
0
0
0
0
0
0
0
70
30
0
0


Foxtail, Giant
20
20
0
0
0
0
0
0
90
70
80
0



Galium

0
0
0
0
0
0
0
0
70
60
30
0



Kochia

0
0
0
0
0
0
0
0
40
0
0
0


Pigweed
0
0
0
0
0
0
0
0
20
0
0
0


Ragweed
0
0
0
0
0
0
0
0
0
0
0
0


Ryegrass, Italian
0
0
0
0
0
0
0
0
0
0
20
0


Wheat
0
0
0
0
0
0
0
0
50
0
20
0











125 g ai/ha
Compounds




















Postemergence
545
546
547
549
550
551
552
553
554
557
558
559
560





Barnyardgrass
0
80
70
40
80
10
80
90
80
0
80
90
90


Blackgrass
0
0
0
0
0
0
30
50
60
0
20
20
30


Corn
0
0
0
0
0
0
20
80
40
0
0
0
0


Foxtail, Giant
0
70
80
20
80
50
70
70
70
0
70
90
90



Galium

0
0
0
0
0
0
40
60
60
0
30
50
40



Kochia

0
0
0
0
0
0
0
30
20
0
20
30
40


Pigweed
0
0
0
0
0
0
0
20
0
0
0
0
0


Ragweed
0
0
0
0
0
0
0
30
0
0
0
0
0


Ryegrass, Italian
0
0
0
0
0
0
30
60
40
0
0
0
0


Wheat
0
0
0
0
0
0
0
40
20
0
0
0
0











125 g ai/ha
Compounds





















Postemergence
561
562
563
564
565
566
567
568
569
570
571
572
573
574





Barnyardgrass
90
90
90
90
80
90
90
100
90
100
90
90
90
90


Blackgrass
50
60
40
40
40
20
60
60
60
60
70
70
70
60


Corn
10
40
20
70
0
0
70
60
20
60
60
60
80
60


Foxtail, Giant
90
90
90
90
80
90
90
90
90
90
90
90
90
80



Galium

60
60
70
70
60
60
40
60
40
50
50
50
60
40



Kochia

70
70
70
80
20
80
20
70
20
50
30
20
50
30


Pigweed
60
70
0
40
20
30
20
30
0
20
20
30
30
20


Ragweed
20
50
0
50
0
0
0
30
30
0
0
0
20
0


Ryegrass, Italian
20
70
40
60
20
30
70
70
40
50
60
30
70
50


Wheat
30
50
20
40
0
0
30
30
30
30
60
60
70
40











125 g ai/ha
Compounds





















Postemergence
575
576
577
587
588
589
590
591
592
593
594
595
596
597





Barnyardgrass
90
90
90
80
80
60
90
90
80
90
90
90
90
0


Blackgrass
70
50
70
20
20
20
50
50
30
50
50
20
20
0


Corn
70
80
60
40
0
10
50
70
50
30
60
30
20
0


Foxtail, Giant
90
90
90
80
80
80
90
90
80
90
90
90
90
0



Galium

50
50
30
0
0
0
20
40
20
0
0
0
30
0



Kochia

0
30
0
0
0
0
0
20
0
0
0
0
40
0


Pigweed
0
0
0
0
20
0
0
20
0
0
0
20
0
0


Ragweed
0
30
0
0
0
0
0
0
0
0
0
0
0
0


Ryegrass, Italian
60
30
30
0
0
20
30
0
0
0
20
20
0
0


Wheat
40
60
40
40
0
0
20
50
30
0
30
30
0
0











125 g ai/ha
Compounds



















Postemergence
598
599
600
601
602
605
606
607
608
609
610
611





Barnyardgrass
10
0
0
20
0
0
50
20
0
50
70
90


Blackgrass
0
0
0
0
0
0
0
0
20
30
50
50


Corn
0
0
0
0
0
0
0
0
0
20
20
50


Foxtail, Giant
0
0
0
20
0
20
70
20
40
70
90
90



Galium

0
0
0
0
0
0
60
0
50
40
50
50



Kochia

0
0
0
0
0
0
0
0
50
20
50
60


Pigweed
0
0
0
0
0
0
50
0
30
0
50
20


Ragweed
0
0
0
0
0
0
0
0
0
0
0
0


Ryegrass, Italian
0
0
0
0
0
0
0
0
30
30
0
40


Wheat
0
0
0
0
0
0
0
0
0
0
0
40











125 g ai/ha
Compounds





















Postemergence
612
613
614
615
616
617
618
619
620
621
622
623
624
625





Barnyardgrass
70
70
80
0
90
90
90
0
20
90
90
90
80
80


Blackgrass
40
40
30
0
50
40
50
0
0
0
30
50
40
30


Corn
50
50
0
0
70
80
80
0
0
0
50
60
0
10


Foxtail, Giant
70
90
80
0
90
90
90
0
30
70
80
90
80
90



Galium

30
60
30
0
60
60
50
0
0
30
60
50
30
30



Kochia

20
60
0
0
50
50
40
0
0
0
40
40
0
30


Pigweed
20
50
0
0
40
30
0
0
0
0
40
60
20
20


Ragweed
0
20
0
0
0
20
0
0
0
0
0
20
0
0


Ryegrass, Italian
20
60
0
0
50
20
40
0
0
0
30
30
30
20


Wheat
30
40
0
0
60
50
50
0
0
0
30
40
20
0











125 g ai/ha
Compounds

















Postemergence
630
631
632
633
634
635
636
637
638
639





Barnyardgrass
80
0
90
90
40
80
90
90
90
90


Blackgrass
0
0
50
20
0
40
60
50
50
60


Corn
0
0
20
0
0
40
70
70
70
40


Foxtail, Giant
30
0
90
90
50
90
90
90
90
90



Galium

0
0
50
0
30
40
50
50
60
40



Kochia

0
0
60
40
0
60
50
0
20
60


Pigweed
0
0
0
0
0
60
30
50
20
20


Ragweed
0
0
20
0
0
0
0
0
0
0


Ryegrass, Italian
0
0
30
0
0
0
50
20
30
30


Wheat
0
0
30
0
0
20
60
70
60
60











125 g ai/ha
Compounds





















Postemergence
640
641
642
643
644
645
646
647
648
649
650
651
652
653





Barnyardgrass
90
90
70
90
90
90
90
80
70
60
90
90
90
60


Blackgrass
0
30
20
50
60
60
70
20
30
20
50
60
60
50


Corn
0
0
50
0
70
20
70
10
0
0
40
80
30
0


Foxtail, Giant
80
90
20
90
90
90
90
90
10
30
90
80
80
60



Galium

40
40
50
0
50
50
40
20
20
50
50
60
30
40



Kochia

0
0
20
0
20
0
60
0
0
30
0
0
0
0


Pigweed
0
0
0
0
20
0
20
0
30
0
0
0
0
0


Ragweed
0
0
0
0
0
10
0
0
0
20
0
0
0
0


Ryegrass, Italian
0
0
40
30
50
20
60
0
30
30
60
50
50
40


Wheat
0
0
0
0
50
30
40
20
0
0
30
40
0
30











125 g ai/ha
Compounds





















Postemergence
654
655
656
657
658
659
660
661
662
663
664
665
666
667





Barnyardgrass
90
70
90
90
70
70
50
90
90
90
90
90
90
90


Blackgrass
30
20
0
0
40
40
0
50
60
60
50
40
60
60


Corn
20
0
0
0
0
0
0
50
80
30
50
40
60
70


Foxtail, Giant
70
40
20
0
0
90
80
90
90
90
90
90
90
90



Galium

40
30
0
0
60
0
0
50
60
50
50
50
30
50



Kochia

20
30
20
0
0
20
0
60
70
20
60
0
0
50


Pigweed
0
0
0
0
0
0
0
0
20
0
20
0
0
0


Ragweed
0
0
0
0
0
0
0
10
20
30
10
0
0
0


Ryegrass, Italian
30
0
0
0
30
0
0
30
40
40
30
30
20
60


Wheat
0
0
0
0
0
0
0
30
80
50
50
30
20
40













125 g ai/ha
Compounds


















Postemergence
668
674
675
676
677
678
679
680
681







Barnyardgrass
90
30
40
50
80
70
40
30
40



Blackgrass
60
0
0
20
0
30
30
20
0



Corn
20
0
0
0
0
10
20
20
0



Foxtail, Giant
90
30
50
20
20
20
0
0
0




Galium

20
0
0
0
0
0
40
0
30




Kochia

20
0
0
0
0
0
0
0
0



Pigweed
0
0
0
0
0
0
0
0
0



Ragweed
0
0
0
0
0
0
0
0
0



Ryegrass, Italian
0
0
0
0
0
0
0
0
0



Wheat
20
0
0
0
0
0
0
0
0












125 g ai/ha
Compounds





















Postemergence
682
683
684
685
686
687
688
689
690
691
692
693
694
695





Barnyardgrass
0
0
40
40
90
90
90
90
80
80
70
70
50
80


Blackgrass
0
0
0
0
20
30
50
50
60
50
50
10
10
0


Corn
0
20
0
30
0
0
40
60
70
60
0
40
0
80


Foxtail, Giant
20
80
40
40
80
80
90
80
80
80
70
80
50
80



Galium

0
0
0
0
0
0
40
50
70
70
0
60
0
50



Kochia

0
0
0
0
0
0
40
30
50
70
40
60
0
30


Pigweed
0
0
0
0
0
0
30
30
60
40
40
10
20
20


Ragweed
0
0
0
0
20
30
30
0
60
50
0
0
0
20


Ryegrass, Italian
0
0
0
0
20
20
40
30
50
50
50
50
0
0


Wheat
0
0
0
0
0
0
20
20
50
50
0
0
0
20











125 g ai/ha
Compounds


















Postemergence
696
697
698
699
700
701
702
703
704
705
706





Barnyardgrass
80
80
70
50
70
60
70
60
70
0
0


Blackgrass
30
30
30
30
0
0
0
0
0
0
0


Corn
40
70
80
30
0
0
0
0
0
0
0


Foxtail, Giant
80
80
80
50
70
60
30
50
70
0
0



Galium

50
50
50
50
40
0
0
0
20
0
0



Kochia

30
60
50
30
30
0
0
0
0
0
0


Pigweed
30
50
40
20
0
0
0
0
0
0
0


Ragweed
20
30
20
0
20
0
0
0
0
0
0


Ryegrass, Italian
30
20
30
0
30
0
0
0
0
0
0


Wheat
30
20
30
0
0
0
0
0
0
0
0













125 g ai/ha
Compounds














Postemergence
711
712
714
715
716







Barnyardgrass
0
0
0
0
0



Blackgrass
0
0






Corn
0
0
0
0
0



Crabgrass, Large


0
0
0



Foxtail, Giant
0
0
0
0
0




Galium

0
0







Kochia

0
0






Morningglory


0
0
0



Pigweed
0
0
0
0
0



Ragweed
0
0






Ryegrass, Italian
0
0






Velvetleaf


0
0
0



Wheat
0
0
0
0
0












125 g ai/ha
Compounds





















Postemergence
717
718
719
720
721
722
723
724
725
726
727
728
729
730





Barnyardgrass
90 
70 
90
90 
10 
20 
0
0
70 
90
80 
90 
0
100 


Blackgrass
0
20 
60
20 
0
0
0
0
0
50
30 
0
0
50


Corn
0
0
90
0
0
0
0
0
0
60
0
0
0
20


Crabgrass, Large
















Foxtail, Giant
30 
30 
90
20 
0
0
0
0
0
90
40 
0
0
90



Galium

40 
40 
60
50 
20 
0
0
0
20 
50
0
20 
0
50



Kochia

20 
30 
60
50 
0
0
0
0
0
30
0
20 
0
70


Morningglory
















Pigweed
0
0
50
0
0
0
0
0
0
50
0
0
0
20


Ragweed
0
0
30
0
0
0
0
0
0
30
0
20 
0
20


Ryegrass, Italian
0
0
50
0
0
0
0
0
0
40
0
20 
0
40


Velvetleaf
















Wheat
0
0
80
0
0
0
0
0
0
30
0
0
0
30











125 g ai/ha
Compounds





















Postemergence
731
732
733
734
735
736
737
738
739
740
741
742
743
744





Barnyardgrass
70 
90
90 
90
90
90
40
80
90
90
0
90
90
60


Blackgrass
0
50
0
20
50
60
30
 0
 0
30
0
40
30
20


Corn
0
70
0
40
80
90
40
20
20
70
0
70
60
40


Crabgrass, Large
















Foxtail, Giant
50 
90
80 
90
90
90
70
70
90
90
0
90
90
80



Galium

20 
30
20 
30
40
50
30
50
50
50
0
50
50
30



Kochia

0
20
0
 0
30
20
 0
20
30
40
0
30
30
30


Morningglory
















Pigweed
0
 0
0
 0
20
20
20
20
20
40
0
 0
 0
 0


Ragweed
0
 0
0
10
 0
 0
 0
 0
30
 0
0
20
 0
20


Ryegrass, Italian
0
50
20 
20
60
80
50
 0
20
50
0
60
40
30


Velvetleaf
















Wheat
0
80
20 
50
50
50
40
 0
 0
50
0
60
50
50











125 g ai/ha
Compounds





















Postemergence
745
746
747
748
749
750
751
752
753
754
755
756
757
758





Barnyardgrass
90
20 
40
40 
0
70 
60 
60
50 
60 
0
90
90
70 


Blackgrass
40
20 
30
0
0
0
20 
 0
0
0
0
 0
60
0


Corn
90
0
 0
0
0
0
0
 0
0
0
0
50
70
20 


Crabgrass, Large
















Foxtail, Giant
90
50 
70
0
0
20 
30 
50
0
60 
0
80
90
80 



Galium

60
50 
60
0
0
0
40 
70
0
0
0
50
50
40 



Kochia

70
0
20
0
0
0
0
40
0
0
0
20
20
0


Morningglory
















Pigweed
70
0
30
0
0
0
0
 0
0
0
0
 0
20
0


Ragweed
40
0
 0
0
0
0
0
20
0
0
0
20
 0
0


Ryegrass, Italian
50
0
 0
0
0
0
0
20
0
0
0
40
20
0


Velvetleaf
















Wheat
60
0
 0
0
0
0
0
 0
0
0
0
30
60
0











125 g ai/ha
Compounds





















Postemergence
759
760
761
762
763
764
765
766
767
768
769
770
771
772





Barnyardgrass
70 
80 
70 
90 
0
80 
70 
10 
70 
70 
50 
60
90
0


Blackgrass
0
0
0
0
0
0
0
0
0
0
0
 0
70
0


Corn
0
0
0
0
0
0
0
0
0
30 
0
50
40
0


Crabgrass, Large
















Foxtail, Giant
20 
80 
60 
20 
0
0
0
0
0
80 
70 
70
90
30 



Galium

0
0
0
0
0
0
0
0
0
30 
50 
60
50
0



Kochia

0
0
0
0
0
0
0
0
0
0
0
40
50



Morningglory
















Pigweed
0
0
0
0
0
0
0
0
0
0
0
30
 0
0


Ragweed
0
0
0
0
0
0
0
0
0
0
0
 0
20
0


Ryegrass, Italian
0
0
0
0
0
30 
40 
0
0
30 
30 
 0
20
0


Velvetleaf
















Wheat
0
0
0
0
0
0
0
0
0
0
0
 0
30
0











125 g ai/ha
Compounds





















Postemergence
773
774
775
776
777
778
779
780
781
782
783
785
786
787





Barnyardgrass
0
0
50
80
70 
80
90
60
90
90
0
90
80 
30


Blackgrass
0
0
 0
30
0
10
70
50
70
70
0
20
0
 0


Corn
0
0
20
30
40 
 0
80
40
60
60
0
 0
0
 0


Crabgrass, Large
















Foxtail, Giant
0
0
60
80
30 
70
80
60
80
90
0
70
40 
20



Galium

0
0
40
20
0
60
60
50
60
70
0
50
10 
60



Kochia


0
40
20
0
60
30
30
 0
10
0
 0
0
60


Morningglory
















Pigweed
0
0
 0
 0
0
10
 0
 0
 0
 0
0
 0
0
60


Ragweed
0
0
20
 0
0
 0
20
 0
 0
 0
0
 0
0
50


Ryegrass, Italian
0
0
20
20
0
20
40
 0
20
40
0
30
0
20


Velvetleaf
















Wheat
0
0
20
30
30 
 0
80
30
50
60
0
 0
0
 0











125 g ai/ha
Compounds





















Postemergence
788
789
790
791
792
793
794
795
796
797
798
799
800
801





Barnyardgrass
80
80
80
60 
0
0
30 
70 
90
90
80
70
80
90


Blackgrass
20
40
40
0
0
0
0
0
30
 0
40
30
20
60


Corn
20
20
30
0
0
0
0
0
90
70
40
20
20
60


Crabgrass, Large
















Foxtail, Giant
70
30
50
30 
0
0
30 
50 
90
90
70
80
80
90



Galium

50
40
50
60 
0
0
0
0
40
30
20
50
30
60



Kochia

40
 0
40
20 
0
0
0
0
 0
 0
 0
30
 0
40


Morningglory
















Pigweed
60
 0
20
0
0
0
0
0
20
20
20
20
40
30


Ragweed
40
 0
30
0
0
0
0
0
 0
 0
 0
 0
 0
50


Ryegrass, Italian
20
 0
 0
0
0
0
0
0
40
40
40
20
20
60


Velvetleaf
















Wheat
 0
20
20
0
0
0
0
0
60
60
20
20
20
30











125 g ai/ha
Compounds





















Postemergence
802
803
804
805
806
807
808
809
810
811
812
813
814
815





Barnyardgrass
80
80
70
0
0
80 
70 
0
70 
40 
90
80
0
100 


Blackgrass
60
50
20
0
0
0
0
0
0
0
80
80
0
50


Corn
70
90
50
0
0
70 
0
0
0
0
80
40
0
50


Crabgrass, Large
















Foxtail, Giant
90
90
80
0
0
80 
80 
0
80 
60 
90
80
0
90



Galium

60
60
50
0
0
0
0
0
0
0
50
30
0
50



Kochia

40
70
70
0
0
0
0
0
0
0
20
 0
0
40


Morningglory
















Pigweed
40
40
60
0
0
0
0
0
0
0
 0
 0
0
20


Ragweed
30
30
 0
0
0
0
0
0
0
0
 0
 0
0
 0


Ryegrass, Italian
40
40
 0
0
0
0
0
0
0
0
30
20
0
60


Velvetleaf
















Wheat
30
40
20
0
0
30 
0
0
0
0
60
30
0
30











125 g ai/ha
Compounds





















Postemergence
816
817
818
819
820
821
822
823
824
825
826
827
828
829





Barnyardgrass
90
90
90
100 
90
90
90
90
90
80
100 
70
70
80


Blackgrass
60
40
30
60
40
70
 0
20
20
40
80
40
50
40


Corn
90
50
40
40
30
40
20
 0
 0
20
80
20
40
30


Crabgrass, Large
















Foxtail, Giant
90
90
90
90
90
80
90
90
90
90
90
80
90
90



Galium

60
40
50
50
30
50
20
30
40
30
50
40
30
30



Kochia

30
 0
40
30
20
30
 0
20
 0
 0
30
 0
 0
 0


Morningglory
















Pigweed
 0
 0
20
30
20
 0
 0
20
 0
 0
30
 0
 0
 0


Ragweed
 0
 0
 0
 0
20
 0
 0
20
30
20
50
 0
 0
 0


Ryegrass, Italian
60
30
40
70
30
20
20
 0
30
20
60
 0
20
20


Velvetleaf
















Wheat
30
50
 0
30
40
0
 0
 0
 0
40
60
20
20
30











125 g ai/ha
Compounds





















Postemergence
830
831
832
833
834
835
836
837
838
839
840
841
842
843





Barnyardgrass
90
30 
70 
90
90
90
100 
90
90
60
80
80
90
40 


Blackgrass
20
0
0
40
60
40
70




30
30
0


Corn
 0
0
0
20
40
30
70
60
70
30
30
 0
20
0


Crabgrass, Large
















Foxtail, Giant
70
20 
0
90
90
90
90
90
90
60
90
90
90
70 



Galium

30
20 
50 
40
60
30
50
50
50
80
50
40
50
30 



Kochia

30
0
20 
30
40
 0
50
20
70
70
 0
30
30
40 


Morningglory
















Pigweed
 0
0
0
 0
20
20
30
30
80
80
 0
 0
30
20 


Ragweed
 0
0
20 
 0
 0
 0
 0
10
40
60
 0
 0
30
0


Ryegrass, Italian
20
20 
20 
60
60
50
60
50
30
50
 0
20
20
0


Velvetleaf
















Wheat
 0
0
0
 0
30
 0
40
 0
30
50
20
 0
30
0











125 g ai/ha
Compounds





















Postemergence
844
845
846
847
848
849
850
851
852
853
854
855
856
857





Barnyardgrass
0
80
90
0
90 
90
90
90 
90 
90 
0
90
80
70


Blackgrass
0
40
50
0
0
30
 0
0
0
20 
0
60
60
30


Corn
0
30
60
0
0
70
30
0
0
0
0
70
80
40


Crabgrass, Large
















Foxtail, Giant
0
90
90
0
70 
90
80
90 
80 
90 
50 
90
90
70



Galium

0
20
 0
0
30 
60
30
30 
0
0
0
 0
40
20



Kochia

0
 0
40
0
0
 0
 0
0
0
0
0
 0
30
20


Morningglory
















Pigweed
0
 0
 0
0
0
 0
 0
0
0
0
0
20
20
30


Ragweed
0
 0
 0
0
0
 0
 0
0
0
0
0
 0
 0
 0


Ryegrass, Italian
0
30
70
0
0
 0
 0
0
0
0
0
20
40
20


Velvetleaf
















Wheat
0
 0
 0
0
0
30
20
20 
0
0
0
50
50
30











125 g ai/ha
Compounds





















Postemergence
858
859
860
861
862
863
864
865
866
867
868
869
870
871





Barnyardgrass
80
80
30 
90
30
70
90
0
60
90
20 
80 
0
50


Blackgrass
 0
30
0
70
 0
 0
50
0
 0
30
0
0
0
 0


Corn
20
50
0
80
20
30
60
0
30
60
0
0
0
20


Crabgrass, Large
















Foxtail, Giant
80
80
60 
90
60
20
70
0
70
80
0
60 
0
40



Galium

30
50
20 
60
60
30
20
0
20
30
0
0
0
50



Kochia

20
20
0
60
40
40
 0
0
20
 0
0
0
0
 0


Morningglory
















Pigweed
20
20
0
50
60
50
20
0
 0
 0
0
0
0
 0


Ragweed
 0
 0
0
 0
 0
 0
 0
0
 0
 0
0
0
0
 0


Ryegrass, Italian
20
20
0
40
20
 0
50
0
20
20
0
0
0
20


Velvetleaf
















Wheat
20
20
20 
50
 0
 0
50
0
 0
20
0
0
0
20











125 g ai/ha
Compounds





















Postemergence
872
873
874
875
876
877
878
879
880
881
882
883
885
886





Barnyardgrass
90
90
90
90
60 
60
100 
100 
90
90 
80
90 
70 
90


Blackgrass
20
50
60
20
0
 0
60
70
 0
0
40
0
0
20


Corn
30
70
50
20
0
 0
50
60
20
0
80
0
0
40


Crabgrass, Large
















Foxtail, Giant
80
90
90
90
40 
70
80
80
80
80 
70
70 
40 
90



Galium

50
50
20
40
0
20
50
50
60
0
50
0
20 
 0



Kochia

50
60
20
40
50 
20
20
60
20
30 
60
30 
0
 0


Morningglory
















Pigweed
30
30
 0
 0
0
 0
 0
20
50
0
30
0
0
 0


Ragweed
 0
30
20
20
0
 0
20
20
40
0
 0
0
0
 0


Ryegrass, Italian
 0
40
20
20
0
20
40
70
50
30 
40
0
0
20


Velvetleaf
















Wheat
20
30
20
 0
0
30
60
70
40
0
 0
0
0
 0











125 g ai/ha
Compounds





















Postemergence
887
888
889
890
891
892
893
894
895
896
897
898
899
900





Barnyardgrass
80 
90 
70
90
50 
90 
100 
90
90
90
90
80
80
80


Blackgrass
0
20 
20
20
0
0
30
 0
60
40
30
50
40
40


Corn
0
0
20
20
20 
0
80
60
80
20
30
70
40
50


Crabgrass, Large
















Foxtail, Giant
70 
30 
40
70
40 
90 
90
90
90
90
80
80
90
80



Galium

0
0
30
50
30 
20 
50
40
70
40
40
 0
 0
20



Kochia

0
0
 0
60
0
40 
60
50
70
20
30
 0
 0
30


Morningglory
















Pigweed
0
0
 0
 0
0
0
20
 0
40
20
 0
40
 0
50


Ragweed
0
0
 0
 0
0
0
30
 0
 0
 0
20
 0
20
10


Ryegrass, Italian
0
0
40
 0
0
60 
60
50
60
50
20
50
30
40


Velvetleaf
















Wheat
0
0
 0
 0
0
0
30
20
40
30
30
40
30
50











125 g ai/ha
Compounds





















Postemergence
901
902
903
904
905
906
907
908
909
910
911
912
913
914





Barnyardgrass
60
60 
80 
80
70 
0
50 
20 
50 
90
90
80
90 
0


Blackgrass
20
0
0
30
0

0
0
0
50
50
30
0
0


Corn
40
0
0
 0
0
0
0
0
0
70
80
30
0
0


Crabgrass, Large
















Foxtail, Giant
90
30 
80 
80
60 
0
60 
30 
40 
90
90
90
30 
70 



Galium

 0
0
10 
30
0
0
0
0
0
30
40
 0
30 
60 



Kochia

30
0
0
30
0
0
0
0
0
20
50
 0
0
70 


Morningglory
















Pigweed
 0
0
0
 0
0
0
0
0
0
 0
 0
 0
0
80 


Ragweed
 0
0
0
 0
0
0
0
0
0
10
 0
 0
30 
20 


Ryegrass, Italian
 0
0
0
 0
0
0
0
0
0
50
70
20
0
0


Velvetleaf
















Wheat
20
0
0
 0
0
0
0
0
0
 0
50
20
0
0











125 g ai/ha
Compounds





















Postemergence
915
916
917
918
919
920
921
922
923
924
925
926
927
928





Barnyardgrass
90
30 
0
0
0
40 
90
90 
0
90 
40 
40 
0
90


Blackgrass
40
0
0
40 
0
0
20
0
0
0
0
0
0
30


Corn
 0
0
0
0
0
0
20
0
0
0
0
0
0
40


Crabgrass, Large
















Foxtail, Giant
90
0
0
0
0
20 
90
50 
0
90 
40 
40 
0
90



Galium

50
30 
0
0
0
0
 0
0
0
0
0
0
0
50



Kochia

20
0
0
0
0
0
 0
0
0
0
0
0
0
40


Morningglory
















Pigweed
60
0
0
0
0
0
 0
0
0
0
0
0
0
20


Ragweed
30
0
0
0
0
0
 0
0
0
0
0
0
0
 0


Ryegrass, Italian
30
0
0
0
0
0
20
0
0
0
0
0
0
50


Velvetleaf
















Wheat
40
0
0
0
0
0
20
0
0
0
0
0
0
40











125 g ai/ha
Compounds





















Postemergence
929
930
931
932
933
934
935
936
937
938
939
940
941
942





Barnyardgrass
90
80
80
90
90
60
70
60
70
80
80 
10 
50 
60


Blackgrass
40
20
20
40
20
 0
60
30
30
40
0
0
0
70


Corn
40
40
70
20
40
20
40
30
20
60
0
0
0
 0


Crabgrass, Large
















Foxtail, Giant
90
80
90
90
90
90
90
90
90
80
90 
0
60 
80



Galium

50
40
40
40
50
60
40
40
70
50
20 
0
20 
50



Kochia

40
20
30
30
50
20
30
20
30
40
0
0
0
30


Morningglory
















Pigweed
20
30
20
40
 0
20
20
20
60
50
0
0
0
70


Ragweed
20
 0
 0
 0
 0
 0
 0
 0
20
 0
0
0
0
 0


Ryegrass, Italian
50
30
30
30
40
 0
20
 0
20
20
0
0
0
 0


Velvetleaf
















Wheat
30
30
30
30
20
 0
30
30
20
40
20 
0
0
20











125 g ai/ha
Compounds





















Postemergence
943
944
945
946
947
948
949
950
951
952
953
954
955
956





Barnyardgrass
70
80
80 
60 
20 
70 
90 
90 
70 
60 
90 
60 
90
90


Blackgrass
40
60
0
0
0
0
0
0
0
0
0
0
 0
40


Corn
20
30
0
0
0
0
0
0
0
0
0
0
 0
50


Crabgrass, Large
















Foxtail, Giant
90
90
0
0
30 
70 
20 
0
0
50 
90 
60 
80
80



Galium

70
20
20 
0
0
0
0
20 
0
0
20 
0
20
40



Kochia

30
 0
0
0
0
0
0
0
0
0
30 
0
20
30


Morningglory
















Pigweed
40
30
0
0
0
0
0
0
0
0
0
0
 0
 0


Ragweed
 0
40
0
0
0
0
0
0
0
0
0
0
 0
20


Ryegrass, Italian
 0
30
0
0
0
0
0
20 
0
0
0
0
30
50


Velvetleaf
















Wheat
 0
40
0
0
0
0
0
0
0
0
0
0
 0
30











125 g ai/ha
Compounds





















Postemergence
957
958
959
960
961
962
963
964
965
966
967
968
969
970





Barnyardgrass
80
70 
90
50 
90
90
90 
60 
80
60 
80 
20 
50
0


Blackgrass
20
30 
30
20 
30
20
0
0
30
20 
0
0
 0
0


Corn
 0
0
30
0
20
 0
0
0
30
0
0
0
50
0


Crabgrass, Large
















Foxtail, Giant
 0
90 
80
20 
30
90
90 
60 
70
40 
80 
0
50
0



Galium

40
30 
40
0
30
30
30 
40 
40
20 
0
0
20
0



Kochia

20
0
50
0
50
20
20 
0
 0
0
0
0
 0
0


Morningglory
















Pigweed
 0
0
 0
0
 0
 0
0
0
 0
0
0
0
 0
0


Ragweed
 0
0
 0
0
20
 0
0
0
 0
0
0
0
 0
0


Ryegrass, Italian
20
0
30
30 
20
20
20 
0
 0
0
0
0
20
0


Velvetleaf
















Wheat
 0
0
20
0
 0
30
0
0
20
0
0
0
30
0











125 g ai/ha
Compounds





















Postemergence
971
972
973
974
975
976
977
978
979
980
981
982
983
984





Barnyardgrass
80
50
30










100 


Blackgrass
50
 0
60
70
50
40
 0
60
60
0
0
70
30
30


Corn
70
60
 0
70
20
60
 0
60
30
0
0
60
20
80


Crabgrass, Large
















Foxtail, Giant
80
60
70
90
90
90
90
90
90
90 
70 
90
90
90



Galium

40
30
50
50
50
 0
40
50
40
0
0

30
30



Kochia

40
 0

70
40
30
70
 0
30
0
0
50
50
50


Morningglory
















Pigweed
50
30
 0
40
30
 0
30
 0
40
0
0
 0
 0
 0


Ragweed
 0
30
 0
20
 0
 0
20
 0
20
0
0
20
 0
 0


Ryegrass, Italian
50
20
20
70
20
20
 0
50
20
0
0
60
20
20


Velvetleaf
















Wheat
50
40
 0
70
20
40
 0
70
50
0
0
70
30
20











125 g ai/ha
Compounds





















Postemergence
985
986
987
988
989
990
991
992
993
994
995
996
997
998





Barnyardgrass
0
80
80 
80
80 
90
30 
0
90
100 
60
0
0
0


Blackgrass
0
40
0
30
0
 0
0
0
70
60
50
0
0
0


Corn
0
80
0
20
0
40
0
0
80
70
30
0
0
0


Crabgrass, Large
















Foxtail, Giant
0
90
60 
80
50 
80
80 
0
90
90
80
0
0
0



Galium

0
30
40 
50
20 
60
0
0
60
50
40
0
0
0



Kochia

0
30
0
10
0
40


20
40
 0

0
0


Morningglory
















Pigweed
0
 0
0
 0
0
30
0
0
30
 0
 0
0
0
0


Ragweed
0
 0
0
 0
0
 0
0
0
 0
20
 0
0
0
0


Ryegrass, Italian
0
30
0
20
0
20
0
0
50
70
30
0
0
0


Velvetleaf
















Wheat
0
20
0
30
0
 0
0
0
50
70
20
0
0
0











125 g ai/ha
Compounds





















Postemergence
999
1000
1001
1002
1003
1004
1005
1006
1007
1008
1009
1010
1011
1012





Barnyardgrass
100 
60 
0
50 
0
0
0
0
0
0
0
0
0
0


Blackgrass
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Corn
0
0
0
0
0
0
0
10 
0
0
0
0
0
0


Crabgrass, Large
















Foxtail, Giant
40 
0
0
0
0
0
0
0
0
0
0
0
0
0



Galium

0
0
0
0
0
0
0
0
0
0
0
0
0
0



Kochia

40 
40 
0
0
0
0
0
0
0
0
0
0
0
0


Morningglory
















Pigweed
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Ragweed
0
0
0
0
0
0
0
10 
0
0
0
0
0
0


Ryegrass, Italian
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Velvetleaf
















Wheat
0
0
0
0
0
0
0
0
0
0
0
0
0
0











125 g ai/ha
Compounds





















Postemergence
1013
1014
1015
1016
1017
1018
1019
1020
1021
1022
1023
1024
1025
1026





Barnyardgrass
90
90
90
50 
90
90
0
90
100 
60 
90 
90
60 
70 


Blackgrass
 0
 0
 0
0
 0
 0
0
 0
20
0
0
 0
0
0


Corn
80
70
70
0
80
70
0
 0
60
0
0
70
0
0


Crabgrass, Large
















Foxtail, Giant
80
90
80
30 
90
90
0
90
90
50 
70 
70
60 
0



Galium

70
20
40
0
40
30
0
40
50
30 
60 
60
30 
0



Kochia

40
30
 0
0
40
30
0
50
70
30 
50 
50
30 
0


Morningglory
















Pigweed
 0
30
30
0
 0
30
0
30
 0
0
0
30
0
0


Ragweed
 0
 0
 0
0
 0
 0
0
 0
40
0
0
 0
0
0


Ryegrass, Italian
 0
30
30
0
30
30
0
30
40
0
30 
30
0
0


Velvetleaf
















Wheat
40
30
 0
0
20
30
0
 0
40
0
0
 0
0
20 











125 g ai/ha
Compounds





















Postemergence
1027
1028
1029
1030
1031
1032
1033
1034
1035
1036
1037
1038
1039
1040





Barnyardgrass
70 
80 
80
70 
0
0
90 
90
90
70 
70 
90
90
80


Blackgrass
0
30 
30
0
0
0
0
20
40
0
0
30
30
60


Corn
0
0
50
20 
0
0
0
10
50
0
0
60
70
60


Crabgrass, Large
















Foxtail, Giant
20 
80 
80
70 
0
0
30 
20
50
0
0
90
90
80



Galium

50 
40 
20
40 
0
0
40 
40
20
20 
40 
50
40
50



Kochia

0
0
 0
0
0
0
0
20
 0
0
0
40
40
60


Morningglory
















Pigweed
0
0
 0
0
0
0
0
 0
 0
0
0
 0
 0
40


Ragweed
0
0
 0
0
0
0
0
10
 0
0
20 
 0
10
 0


Ryegrass, Italian
0
0
 0
0
0
0
0
 0
40
0
0
20
50
30


Velvetleaf
















Wheat
0
0
30
30 
0
0
0
 0
20
0
0
20
50
20











125 g ai/ha
Compounds





















Postemergence
1041
1042
1043
1044
1045
1046
1047
1048
1049
1050
1051
1052
1053
1054





Barnyardgrass
0
80
50
70
90
90
40 
50
30 
0
0
80
0
0


Blackgrass
0
40
20

40
30
0
20
0
0
0
20
0
0


Corn
0
60
20
 0
20
20
0
20
0
0
0
 0
0
0


Crabgrass, Large
















Foxtail, Giant
0
80
70
60
60
60
50 
60
70 
0
0
70
0
0



Galium

40 
30
20
40
40
50
0
 0
0
0
50 
70
0
0



Kochia

0
30
 0
 0
 0
 0
0
30
0
0
0
40
0
0


Morningglory
















Pigweed
0
20
 0
30
 0
 0
0
30
10 
0
0
30
0
0


Ragweed
0
 0
 0
20
30
 0
0
 0
0
0
0
30
0
0


Ryegrass, Italian
0
30
 0
 0
50
40
0
30
0
0
0
20
0
0


Velvetleaf
















Wheat
0
 0
 0
 0
20
20
0
20
0
0
0
 0
0
0











125 g ai/ha
Compounds





















Postemergence
1055
1056
1057
1058
1059
1060
1061
1062
1063
1065
1066
1067
1068
1069





Barnyardgrass
0
20 
0
70 
40 
100 
80 
90
90
40
70
60
0
0


Blackgrass
0
0
0
30 
0
60
0
30
30
50
60
50
0
0


Corn
0
0
0
0
0
90
0
 0
50
20
40
 0
0
0


Crabgrass, Large
















Foxtail, Giant
0
0
0
0
0
90
20 
90
90
70
90
90
0
0



Galium

0
0
0
50 
0
40
0
50
50
70
50
50
0
0



Kochia

0
0
0
0
0
 0
0
 0
 0
40
 0
30
0
0


Morningglory
















Pigweed
0
0
0
0
0
 0
0
 0
20
40
 0
 0
0
0


Ragweed
0
0
0
80 
0
30
0
30
 0
 0
 0
 0
0
0


Ryegrass, Italian
0
0
0
0
0
50
0
20
30
40
30
 0
0
0


Velvetleaf
















Wheat
0
0
0
0
0
70
0
30
40
20
50
40
0
0











125 g ai/ha
Compounds





















Postemergence
1070
1071
1072
1073
1074
1075
1076
1077
1078
1079
1080
1081
1082
1083





Barnyardgrass
0
90 
100 
70 
90
90
50 
90
10 
90 
50 
90
30 
90


Blackgrass
0
0
20 
0
50
50
20 
30
0
0
0
 0
0
60


Corn
0
0
0
20 
20
70
0
10
0
0
0
20
30 
40


Crabgrass, Large
















Foxtail, Giant
0
80 
90 
0
90
90
50 
90
0
20 
0
80
0
90



Galium

0
0
0




70
0
0
0
20
0
70



Kochia

0
0
0
0
20
30
0
 0
0
20 
0
 0
0
40


Morningglory
















Pigweed
0
0
0
0
 0
 0
0
 0
0
0
0
 0
0
20


Ragweed
0
0
0
30 
 0
40
0
 0
0
0
0
 0
0
30


Ryegrass, Italian
0
0
30 
0
30
70
0
20
0
0
0
 0
0
20


Velvetleaf
















Wheat
0
0
20 
0
40
60
0
 0
0
30 
0
20
0
40











125 g ai/ha
Compounds





















Postemergence
1084
1085
1086
1087
1088
1089
1090
1091
1092
1093
1094
1095
1096
1097





Barnyardgrass
60
90
90 
90
30 
90

0
90
80
40 
0
0
0


Blackgrass
20
20
0
30
0
30
20
0
20
 0
0
0
0
0


Corn
 0
20
30 
 0
0
30
20
0
 0
 0
0
0
0
0


Crabgrass, Large
















Foxtail, Giant
50
60
60 
60
20 
90
80
0
90
90
30 
0
0
0



Galium

 0
60
20 
70
30 

30
0


20 
0
0
0



Kochia

30
20
0
20
0
 0
30
0
20
20
0
0
0
0


Morningglory
















Pigweed
 0
20
0
30
0
 0
 0
30 
20
20
0
0
0
0


Ragweed
 0
 0
0
 0
0
20
 0
0
50
30
0
0
0
0


Ryegrass, Italian
 0
20
0
 0
0
 0
 0
0
 0
 0
0
0
0
0


Velvetleaf
















Wheat
20
20
20 
 0
0
30
20
0
 0
 0
20 
0
0
0











125 g ai/ha
Compounds





















Postemergence
1098
1099
1100
1101
1102
1103
1104
1105
1106
1107
1108
1109
1110
1111





Barnyardgrass
80
70
60 
70
80
70
30 
30 
80 
0
0
100 
90
0


Blackgrass
20
20
0
 0
20
30
0
0
0
0
0
40
60
0


Corn
 0
50
0
30
20
 0
0
0
0
0
0
80
80
0


Crabgrass, Large
















Foxtail, Giant
80
80
70 
70
80
80
0
50 
60 
0
0
90
90
20 



Galium

30
50
0
50
 0
50
0
40 
60 
0
0
50
50
0



Kochia

20
30
0
30
 0

0
20 
60 
0
0
70
70
0


Morningglory
















Pigweed
 0
20
0
30
 0
 0
0
0
20 
0
0
60
50
0


Ragweed
 0
 0
0
 0
 0
30
0
0
0
0
0
50
30
0


Ryegrass, Italian
40
40
20 
20
 0
20
0
0
0
0
0
50
60
0


Velvetleaf
















Wheat
 0
20
0
 0
20
20
0
0
0
0
0
60
70
0











125 g ai/ha
Compounds





















Postemergence
1112
1113
1114
1115
1116
1117
1118
1119
1120
1121
1122
1123
1124
1125





Barnyardgrass
0
0
80 
80
30 
80 
80 
80
90
90
90
90
60 
90


Blackgrass
0
0
20 
30
0
0
20 
50
30
40
40
30
0
40


Corn
0
0
0
40
0
20 
0
20
 0
50
50
20
0
30


Crabgrass, Large
















Foxtail, Giant
0
0
90 
70
0
20 
0
30
90
90
80
90
60 
90



Galium

0
0
0
 0
0
40 
50 
40
40
50
50
40
50 
40



Kochia

0
0
0
20
0
20 
0
40
20
50
60
60
60 
 0


Morningglory
















Pigweed
0
0
0
20
0
0
0
 0
 0
20
20
 0
0
 0


Ragweed
0
0
0
 0
0
0
0
20
 0
20
50
30
0
 0


Ryegrass, Italian
0
0
0
20
0
0
20 
30
20
40
30
30
0
 0


Velvetleaf
















Wheat
0
0
0
20
0
0
20 
20
20
30
50
 0
0
30











125 g ai/ha
Compounds





















Postemergence
1126
1127
1129
1130
1131
1132
1133
1134
1135
1136
1137
1138
1139
1140





Barnyardgrass
90
0
40 
0
70
90 
80
60
0
30 
0
90
60
90


Blackgrass
20
0
0
0
40
30 
30
20
0
0
0
30
40
30


Corn
60
0
0
0
70
60 
50
20
0
0
0
50
60
60


Crabgrass, Large
















Foxtail, Giant
80
0
70 
0
80
80 
90
30
0
20 
0
50
40
90



Galium

50
0
0
0
60
0
70
20
0
0
0
20
50
40



Kochia

50
0
0
0
60
0
30
 0
0
0
0
 0
 0
 0


Morningglory
















Pigweed
 0
0
0
0
50
0
 0
 0
0
0
0
 0
 0
 0


Ragweed
40
0
0
0
50
0
60
 0
0
0
0
 0
 0
 0


Ryegrass, Italian
30
0
0
0
 0
0
20
20
0
0
0
 0
40
50


Velvetleaf
















Wheat
50
0
0
0
50
30 
60
 0
0
0
0
30
50
30











125 g ai/ha
Compounds





















Postemergence
1141
1142
1143
1144
1145
1146
1147
1148
1149
1150
1151
1152
1153
1154





Barnyardgrass
90
30 
50 
90
80
40 
0
80 
90 
40
80
0
90 
70


Blackgrass
30
0
0
40
50
0
0
20 
0
 0
30
0
0
70


Corn
20
0
0
50
50
30 
0
0
0
20
60
0
0
90


Crabgrass, Large
















Foxtail, Giant
90
60 
40 
90
90
20 
0
80 
80 
50
70
20 
60 
90



Galium

90
30 
0
40
 0
0
0
40 
50 
20
20
0
30 
60



Kochia

30
0
0
70
 0
0
0
0
30 
20
30
0
0
60


Morningglory
















Pigweed
50
30 
20 
30
 0
0
0
20 
0
 0
20
0
0
60


Ragweed
30
0
0
70
 0
0
0
0
0
 0
 0
0
0
 0


Ryegrass, Italian
50
0
0
60
20
0
0
0
20 
 0
30
0
0
30


Velvetleaf
















Wheat
20
0
0
50
40
0
0
0
0
 0
40
0
0
40











125 g ai/ha
Compounds





















Postemergence
1155
1156
1157
1158
1159
1160
1161
1162
1163
1164
1165
1166
1167
1168





Barnyardgrass
80 
90
90 
90
90 
80 
0
60 
60 
80 
80
0
50 
0


Blackgrass
0
 0
0
20
0
0
0
0
20 
0
 0
0
0
0


Corn
20 
20
40 
20
0
40 
0
0
0
0
30
0
0
0


Crabgrass, Large
















Foxtail, Giant
30 
90
90 
80
40 
80 
0
40 
0
0
70
20 
30 
20 



Galium

40 
40
50 
20
20 
0
0
50 
20 
30 
60
0
20 
30 



Kochia

0
 0
0
 0
0
0
0
0
0
0
30
0
0
0


Morningglory
















Pigweed
0
 0
0
 0
0
0
0
0
0
0
30
0
0
0


Ragweed
0
 0
0
 0
0
0
0
0
0
0
 0
0
0
0


Ryegrass, Italian
0
20
0
30
0
20 
0
0
0
0
20
0
0
0


Velvetleaf
















Wheat
20 
20
30 
30
0
20 
0
20 
0
0
30
0
50 
20 











125 g ai/ha
Compounds





















Postemergence
1169
1170
1171
1172
1173
1174
1175
1176
1177
1178
1179
1180
1181
1182





Barnyardgrass
80 
60 
70 
0
70
70 
90
90
70
0
0
0
0
0


Blackgrass
0
20 
0
0
 0
0
50
70
60
0
0
0
0
0


Corn
0
0
0
0
 0
50 
30
90
20
0
0
0
0
0


Crabgrass, Large
















Foxtail, Giant
70 
60 
60 
0
80
80 
80
80
50
0
0
0
0
0



Galium

0
30 
0
0
50
0
40
50
20
30 
0
0
0
0



Kochia

20 

0
0
50
0
 0
40
 0
20 

0

0


Morningglory
















Pigweed
0
0
0
0
50
0
20
 0
 0
0
0
0
0
0


Ragweed
0
0
0
0
10
0
30
30
 0
0
0
0
0
0


Ryegrass, Italian
0
0
0
0
20
0
50
30
40
0
0
0
0
0


Velvetleaf
















Wheat
0
0
0
0
 0
30 
40
90
20
0
0
0
0
0











125 g ai/ha
Compounds





















Postemergence
1183
1184
1185
1186
1187
1188
1189
1190
1191
1192
1193
1194
1195
1196





Barnyardgrass
90
80
50
100 
100 
100 
100 
60 
0
100 
70 
0
0
70 


Blackgrass
50
60
50
80
40
70
40
0
0
 0
0
0
0
0


Corn
60
40
20
80
 0
50
20
0
0
40
0
0
0
0


Crabgrass, Large
















Foxtail, Giant
80
80
60
90
80
80
80
20 
0
70
30 
0
0
30 



Galium

 0
20
 0
60
50
60
50
20 
0
50
0
0
0
0



Kochia

 0
 0
 0
60
20
50
20
0
0
40
0
0
0
0


Morningglory
















Pigweed
 0
 0
 0
 0
 0
20
 0
0
0
20
0
0
0
0


Ragweed
 0
 0
 0
70
 0
40
40
0
0
 0
0
0
0
0


Ryegrass, Italian
50
30
20
50
20
40
20
0
0
 0
0
0
0
0


Velvetleaf
















Wheat
50
60
40
60
20
40
20
0
0
 0
0
0
0
0











125 g ai/ha
Compounds





















Postemergence
1197
1198
1199
1200
1201
1202
1203
1204
1205
1206
1207
1208
1209
1210





Barnyardgrass

80
70 
0
70 



40 
70 
70 
100 




Blackgrass
50
20
0
0
0
0
20
50
0
0
0
 0
0
0


Corn
80
 0
0
0
0
20 
40
70
70 
0
0
20
0
0


Crabgrass, Large
















Foxtail, Giant
90
80
70 
0
70 
70 
90
90
80 
50 
50 
70
80 
90 



Galium

60
40
20 
0
30 
0
50
50
20 
30 
20 
40
0
0



Kochia

70
60
20 
0
40 
30 
40
80
0
50 
20 
70
0
0


Morningglory
















Pigweed
50
40
0
0
20 
0
 0
70
0
0
0
30
0
0


Ragweed
50
 0
0
0
0
0
20
20
0
0
0
 0
0
0


Ryegrass, Italian
30
 0
0
0
0
0
 0
70
0
0
0
 0
0
30 


Velvetleaf
















Wheat
50
 0
0
0
0
0
 0
60
30 
0
0
 0
0
0











125 g ai/ha
Compounds





















Postemergence
1211
1212
1213
1214
1215
1216
1217
1218
1219
1220
1221
1222
1223
1224





Barnyardgrass
100 
80 
100 
90




30 
70
30
0
30
70 


Blackgrass
30
0
20
80
0
0
0
0
0
30
60
0
30
0


Corn
80
0
50
80
0
0
0
0
0
30
 0
0
 0
0


Crabgrass, Large
















Foxtail, Giant
80
70 
90
90
70 
20 
90 
0
50 
80
90
20 
90
30 



Galium

50
50 
50
60
0
0
0
0
0
30
40
0
20
0



Kochia

 0
60 
50
60
0
0
0
0





0


Morningglory
















Pigweed
30
50 
 0
30
0
0
0
0
0
20
 0
0
 0
0


Ragweed
 0
0
 0
 0
0
0
0
0
0
20
 0
0
 0
0


Ryegrass, Italian
 0
0
 0
60
0
0
0
0
0
20
20
0
20
0


Velvetleaf
















Wheat
30
0
40
70
0
0
0
0
0
20
20
0
 0
0











125 g ai/ha
Compounds





















Postemergence
1225
1226
1227
1228
1229
1230
1231
1232
1233
1234
1235
1236
1237
1238





Barnyardgrass
90
100 
0
90
100 
30 
80
80
80
90
90
100 
20 
50


Blackgrass
30
20
0
 0
0
0
 0
 0
 0
30
30
30
0
30


Corn
30
30
0
20
0
0
70
 0
70
80
70
60
0
20


Crabgrass, Large
















Foxtail, Giant
90
80
0
80
90 
60 
80
80
80
80
80
30
20 
60



Galium

50
80
0
20
40 
20 
50
20
20
50
50
50
0
20



Kochia


60
0
60
70 
30 



40
30
20
0
30


Morningglory
















Pigweed
30
20
20 
20
40 
30 
 0
 0
 0
20
 0
20
0
 0


Ragweed
40
 0
0
 0
0
0
 0
 0
 0
30
 0
 0
0
 0


Ryegrass, Italian
30
 0
0
 0
0
0
40
30
40
40
 0
 0
0
20


Velvetleaf
















Wheat
30
 0
0
 0
0
0
50
 0
40
40
40
 0
0
 0











125 g ai/ha
Compounds





















Postemergence
1239
1240
1241
1242
1243
1244
1245
1246
1247
1248
1249
1250
1251
1252





Barnyardgrass
90
0
0
20 
0
50 
40 
50 
40 
0
100 
70
80
80


Blackgrass
70
0
0
0
0
0
30 
0
0
0
40
20
 0
50


Corn
50
0
0
0
0
0
0
0
0
0
70
40
20
80


Crabgrass, Large
















Foxtail, Giant
90
0
0
20 
0
50 
20 
20 
0
0
80
80
70
80



Galium

60
0
0
0
0
0
30 
50 
0
0
50
40
50
50



Kochia

40
0
0
0
0
0
0
0
0
0
40
 0
50
20


Morningglory
















Pigweed
50
0
0
0
0
0
0
0
0
0
30
 0
70
 0


Ragweed
20
0
0
0
0
0
0
10 
0
0
 0
 0
 0
 0


Ryegrass, Italian
20
0
0
0
0
0
0
0
0
0
30
20
20
70


Velvetleaf
















Wheat
30
0
0
0
0
0
0
0
0
0
50
40
30
70











125 g ai/ha
Compounds





















Postemergence
1253
1254
1255
1256
1257
1258
1259
1260
1261
1262
1263
1264
1265
1266





Barnyardgrass
90
80 
90
50
0
70 
80
90
90
90
0
0
90
90


Blackgrass
30
0
 0
 0
0
0
 0
70
60
50
0
0
50
60


Corn
 0
20 
60
 0
0
40 
70
90
80
60
0
0
70
90


Crabgrass, Large
















Foxtail, Giant
80
80 
80
60
0
60 
70
80
90
80
0
0
80
80



Galium

50
30 
40
40
0
80 
80
70
60
70
0
0
60
60



Kochia

60
0
20
20
0
0
 0
60
50
50
0
0
70
70


Morningglory
















Pigweed
 0
0
 0
20
0
30 
60
50
30
70
0
0
70
70


Ragweed
 0
0
 0
 0
0
0
 0
50
30
30
0
0
30
50


Ryegrass, Italian
40
0
20
20
0
0
 0
60
50
20
0
0
30
70


Velvetleaf
















Wheat
 0
20 
40
20
0
0
20
90
50
30
0
0
50
50











125 g ai/ha
Compounds





















Postemergence
1267
1268
1269
1270
1271
1272
1273
1274
1275
1276
1277
1278
1279
1280





Barnyardgrass
90 
90 
90
90
60
70
60
90
90 
100 
80 
100 
50 
0


Blackgrass
0
0
40
40
30
40
20
30
0
0
0
0
20 
0


Corn
0
0
80
20
40
50
60
30
0
0
0
0
0
0


Crabgrass, Large
















Foxtail, Giant
90 
90 
80
80
80
80
80
90
70 
60 
70 
80 
20 
0



Galium

0
0
60
70
60
60
50
60
0
0
0
0
30 
0



Kochia

0
0
40
60
40
20
60
70
0
0
0
20 
0
0


Morningglory
















Pigweed
0
0
30
60
30
 0
40
20
0
0
0
0
0
0


Ragweed
0
0
 0
 0
 0
 0
 0
30
0
0
30 
30 
0
0


Ryegrass, Italian
0
20 
30
30
30
30
40
20
0
0
0
0
0
0


Velvetleaf
















Wheat
0
0
60
40
60
50
30
60
0
0
0
0
0
0











125 g ai/ha
Compounds





















Postemergence
1281
1282
1283
1284
1285
1286
1287
1288
1289
1290
1291
1292
1293
1294





Barnyardgrass
20 
100 
0
0
80 
90
90 
0
0
0
90 
0
20 
20 


Blackgrass
0
 0
0
0
0
40
20 
0
0
0
0
0
0
0


Corn
0
30
0
0
0
80
0
0
0
0
30 
0
0
0


Crabgrass, Large
















Foxtail, Giant
20 
80
0
0
70 
90
80 
0
0
0
80 
0
0
20 



Galium

0
70
0
0
30 
40
40 
0
0
0
20 
0
0
0



Kochia

0
60
0
0
0
30
30 
0
0
0
0
0
0
0


Morningglory
















Pigweed
0
20
0
0
20 
20
0
0
0
0
0
0
0
0


Ragweed
0
40
0
0
0
 0
0
0
0
0
0
0
0
0


Ryegrass, Italian
0
40
0
0
0
 0
0
0
0
0
0
0
0
0


Velvetleaf
















Wheat
0
50
0
0
0
 0
0
0
0
0
30 
0
0
0











125 g ai/ha
Compounds





















Postemergence
1295
1296
1297
1298
1299
1300
1301
1302
1303
1304
1305
1306
1307
1308





Barnyardgrass
0
30 
20 
80 
90
80 
20 
60 
0
0
60 
20 
40 
80


Blackgrass
0
0
0
0
20
30 
0
0
0
0
0
0
0
30


Corn
0
0
0
0
40
20 
0
0
0
0
0
0
0
20


Crabgrass, Large
















Foxtail, Giant
0
30 
20 
70 
90
80 
20 
30 
40 
0
80 
0
0
20



Galium

0
0
0
0
40
20 
20 
0
0
0
0
20 
30 
30



Kochia

0
0
0
0
 0
0
0
0

0
0
0
0
 0


Morningglory
















Pigweed
0
0
0
0
 0
0
0
0
0
0
0
0
0
 0


Ragweed
0
0
0
0
 0
0
0
0
0
0
0
0
0
 0


Ryegrass, Italian
0
0
0
0
20
0
0
0
0
0
0
0
0
 0


Velvetleaf
















Wheat
0
0
0
0
30
0
0
0
0
0
0
0
0
20











125 g ai/ha
Compounds





















Postemergence
1309
1310
1311
1312
1313
1314
1316
1317
1318
1319
1320
1321
1323
1324





Barnyardgrass
90 
90 




90
90
80
90
0
90
90
90


Blackgrass
0
0
60
50
0
 0
70
80
70
70
0
30
50
40


Corn
0
0
70
40
0
30
80
80
60
70
0
40
50
60


Crabgrass, Large
















Foxtail, Giant
30 
80 
90
90
90 
90
90
90
90
90
0
90
90
90



Galium

30 
50 
50
50
0
30
60
60
60
60
30 
30
50
30



Kochia

0
0
30
50
20 
50
30
20
 0
20
0
 0
 0
30


Morningglory
















Pigweed
0
0
 0
 0
0
 0
50
30
30
 0
0
 0
 0
 0


Ragweed
0
0
 0
 0
0
 0
30
 0
10
 0
0
 0
 0
20


Ryegrass, Italian
0
0
40
30
0
 0
50
40
20
40
0
20
40
30


Velvetleaf
















Wheat
20 
0
60
30
0
20
60
60
50
60
0
20
50
30











125 g ai/ha
Compounds





















Postemergence
1325
1326
1327
1328
1329
1330
1331
1332
1333
1334
1335
1336
1337
1338





Barnyardgrass
90
70 
90 
60 
90
90
90 
50 
70 
0
0
0
30
80 


Blackgrass

0
0
0
20
50
20 
0
0
0
0
0
 0
0


Corn
 0
0
0
0
30
90
20 
0
0
0
0
0
 0
0


Crabgrass, Large
















Foxtail, Giant
80
0
20 
0
90
90
90 
40 
60 
0
0
0
40
80 



Galium

80
0
30 
0
30
30
0
0
0
50 
0
0
 0
30 



Kochia

70
0
0
0
40
 0
0
0
0
0
0
0
20
0


Morningglory
















Pigweed
70
0
0
0
 0
 0
0
0
10 
30 
0
0
20
0


Ragweed
 0
0
0
0
 0
 0
0
0
0
0
0
0
 0
0


Ryegrass, Italian
 0
0
0
0
 0
 0
0
0
0
0
0
0
20
0


Velvetleaf
















Wheat
 0
0
0
0
 0
50
0
0
0
0
0
0
20
0











125 g ai/ha
Compounds





















Postemergence
1339
1340
1341
1342
1343
1344
1345
1346
1347
1348
1349
1350
1351
1352





Barnyardgrass
90
30 
90 
90 
90
0
90 
80
90
90
90
90
0
60 


Blackgrass
 0
0
0
0
 0
0
20 
20
60
50
20
50
0
30 


Corn
 0
20 
0
0
 0
0
0
40
30
80
 0
50
0
0


Crabgrass, Large
















Foxtail, Giant
80
50 
0
70 
90
0
90 
90
90
90
80
90
0
80 



Galium

50
20 



0
20 

70
70
60






Kochia

20
20 
0
20 
50
0
0
30
80
50
30
70
0
0


Morningglory
















Pigweed
30
0
0
0
 0
0
0
20
90
 0
 0
70
0
0


Ragweed
20
0
0
0
30
0
0
 0
70
20
 0
60
0
0


Ryegrass, Italian
 0
0
0
0
20
0
0
20
40
30
20
20
0
0


Velvetleaf
















Wheat
 0
0
0
0
30
0
0
60
30
60
 0
50
0
20 











125 g ai/ha
Compounds





















Postemergence
1353
1354
1355
1356
1357
1358
1359
1360
1361
1362
1366
1367
1368
1369





Barnyardgrass
90
20 
0
0
0
0
0
0
0
0
70 
30 
50
60


Blackgrass
20
0








0
0
30
20


Corn
 0
0
0
0
0
0
0
0
0
0
0
0
 0
 0


Crabgrass, Large


0
0
0
0
0
0
0
0






Foxtail, Giant
70
60 
0
0
0
0
0
0
0
0
70 
30 
40
50



Galium


40 








70 
0
30
30



Kochia

20
20 








0
0
20
20


Morningglory


0
0
0
0
0
0
0
0






Pigweed
20
0
0
0
0
0
0
0
0
0
80 
20 
 0
20


Ragweed
 0
0








0
0
 0
20


Ryegrass, Italian
 0
0








0
0
40
30


Velvetleaf


0
0
0
0
0
0
0
0






Wheat
 0
0
0
0
0
0
0
0
0
0
0
0
 0
 0











125 g ai/ha
Compounds





















Postemergence
1370
1371
1372
1373
1374
1375
1376
1377
1378
1379
1380
1381
1382
1383





Barnyardgrass

80


0
100 
90 
90
80
100 
60
80
0
100 


Blackgrass
50
40
50
50
0
40
20 
20
30
20
40
40
0
40


Corn
30
40
70
90
0
30
0
50
80
70
50
40
0
80


Crabgrass, Large
















Foxtail, Giant
90
90
90
90
0
90
80 
80
80
80
90
90
0
90



Galium

40
70
60
60
0
50
0
40
60
40
50
50
0
60



Kochia

50
50
70
80
0
50
0
50

30


0
70


Morningglory
















Pigweed
 0
30
60
70
0
 0
0
20
30
20
50
70
0
40


Ragweed
 0
20
60
60
0
20
0
20
40
30
40
50
0
50


Ryegrass, Italian
40
30
20
30
0
20
0
30
40
30
50
50
0
40


Velvetleaf
















Wheat
40
10
70
50
0
30
0
30
60
30
40
30
0
60











125 g ai/ha
Compounds





















Postemergence
1384
1385
1386
1387
1388
1389
1390
1391
1392
1393
1394
1395
1396
1397





Barnyardgrass
90
80 
90
60 
100 
90
90
90
0
90
90 
90
80
90


Blackgrass
 0
20 
70
0
70
50
30
40
0
30
0
70
50
70


Corn
70
0
70
0
60
90
70
 0
0
80
40 
50
60
90


Crabgrass, Large
















Foxtail, Giant
80
70 
90
60 
90
80
90
90
0
90
80 
90
80
90



Galium

30
30 
60
30 
50
60
50
70
0
60
50 
 0
70
60



Kochia

40
0
70
0
30
60
40
70
0
70
0
 0
70
 0


Morningglory
















Pigweed
 0
0
40
0
40
30
40
70
0
60
0
 0
70
 0


Ragweed
40
0
20
0
 0
 0
 0
20
0
50
0
 0
50
 0


Ryegrass, Italian
30
0
40
0
60
70
20
40
0
20
0
20
40
40


Velvetleaf
















Wheat
 0
0
50
0
50
60
30
30
0
30
0
20
70
70













125 g ai/ha
Compounds













Postemergence
1398
1399
1400
1402







Barnyardgrass
100 
90
90
90



Blackgrass
60
20
70
50



Corn
40
 0
40
 0



Crabgrass, Large







Foxtail, Giant
90
90
90
90




Galium

50
60
70
70




Kochia

60
70
70
70



Morningglory







Pigweed
 0
40
60
 0



Ragweed
30
40
50
20



Ryegrass, Italian
40
20
50
 0



Velvetleaf







Wheat
60
20
60
40












31 g ai/ha
Compounds





















Postemergence
770
792
793
794
795
796
797
798
799
800
801
802
803
804





Barnyardgrass
30
0
0
0
20
80
90
40
40
80
80
80
80
20


Blackgrass
0
0
0
0
0
0
0
0
0
0
20
20
20
0


Corn
0
0
0
0
0
70
60
0
0
0
20
20
20
0


Foxtail, Giant
60
0
0
0
0
80
80
20
40
80
70
70
90
60



Galium

30
0
0
0
0
0
0
0
0
0
30
0
30
40



Kochia

0
0
0
0
0
0
0
0
0
0
20
20
50
40


Pigweed
0
0
0
0
0
0
0
0
0
20
30
30
30
50


Ragweed
0
0
0
0
0
0
0
0
0
0
0
0
30
0


Ryegrass, Italian
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Wheat
0
0
0
0
0
30
0
0
0
0
0
0
0
0











31 g ai/ha
Compounds





















Postemergence
805
806
807
808
809
810
811
812
813
814
970
971
972
997





Barnyardgrass
0
0
70
50
0
40
0
90
40
0
0
50
50
0


Blackgrass
0
0
0
0
0
0
0
40
30
0
0
40
0
0


Corn
0
0
0
0
0
0
0
30
30
0
0
70
20
0


Foxtail, Giant
0
0
70
70
0
60
0
70
70
0
0
80
30
0



Galium

0
0
0
0
0
0
0
20
20
0
0
20
0
0



Kochia

0
0
0
0
0
0
0
0
0
0
0
20
0
0


Pigweed
0
0
0
0
0
0
0
0
0
0
0
20
20
0


Ragweed
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Ryegrass, Italian
0
0
0
0
0
0
0
0
0
0
0
20
0
0


Wheat
0
0
0
0
0
0
0
20
0
0
0
30
20
0











31 g ai/ha
Compounds





















Postemergence
1003
1004
1005
1006
1007
1008
1009
1010
1011
1012
1050
1051
1052
1060





Barnyardgrass
0
0
0
0
0
0
0
0
0
0
0
0
30
90


Blackgrass
0
0
0
0
0
0
0
0
0
0
0
0
0
50


Corn
0
0
0
0
0
0
0
0
0
0
0
0
0
70


Foxtail, Giant
0
0
0
0
0
0
0
0
0
0
0
0
30
90



Galium

0
0
0
0
0
0
0
0
0
0
0
30
40
0



Kochia

0
0
0
0
0
0
0
0
0
0
0
0
0
0


Pigweed
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Ragweed
0
0
0
10
0
0
0
0
0
0
0
0
0
0


Ryegrass, Italian
0
0
0
0
0
0
0
0
0
0
0
0
0
50


Wheat
0
0
0
0
0
0
0
0
0
0
0
0
0
30











31 g ai/ha
Compounds





















Postemergence
1061
1062
1063
1065
1066
1067
1068
1069
1070
1071
1072
1074
1075
1076





Barnyardgrass
50
70
70
0
50
20
0
0
0
30
90
80
90
0


Blackgrass
0
0
20
0
0
0
0
0
0
0
0
20
40
0


Corn
0
0
0
0
0
0
0
0
0
0
0
0
20
0


Foxtail, Giant
0
90
80
0
70
30
0
0
0
20
80
70
80
0



Galium

0
0
30
40
0
0
0
0
0
0
0






Kochia

0
0
0
0
0
0
0
0
0
0
0
0
30
0


Pigweed
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Ragweed
0
30
0
0
0
0
0
0
0
0
0
0
0
0


Ryegrass, Italian
0
0
0
0
30
0
0
0
0
0
0
20
0
0


Wheat
0
0
0
0
0
0
0
0
0
0
0
0
0
0











31 g ai/ha
Compounds





















Postemergence
1077
1078
1079
1080
1081
1082
1083
1084
1085
1086
1087
1088
1089
1090





Barnyardgrass
70
0
20
0
30
0
90
10
40
30
20
0
60



Blackgrass
0
0
0
0
0
0
50
0
0
0
0
0
0
0


Corn
0
0
0
0
0
0
20
0
20
0
0
0
0
0


Foxtail, Giant
50
0
0
0
10
0
80
0
0
10
30
0
80
20



Galium

20
0
0
0
0
0
60
0
40
0
30
20

30



Kochia

0
0
0
0
0
0
20
0
0
0
0
0
0
0


Pigweed
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Ragweed
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Ryegrass, Italian
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Wheat
0
0
0
0
0
0
40
0
0
0
0
0
0
0











31 g ai/ha
Compounds





















Postemergence
1091
1092
1093
1103
1104
1105
1106
1107
1108
1109
1110
1141
1142
1143





Barnyardgrass
0
50
40
40
0
0
30
0
0
90
80
60
0
0


Blackgrass
0
0
0
20
0
0
0
0
0
20
0
0
0
0


Corn
0
0
0
0
0
0
0
0
0
40
30
0
0
0


Foxtail, Giant
0
30
30
50
0
0
0
0
0
70
60
60
0
0



Galium

0


30
0
30
40
0
0
30
20
60
0
0



Kochia

0
0
0
0
0
0
0
0
0
20
30
0
0
0


Pigweed
0
0
0
0
0
0
10
0
0
20
20
30
0
0


Ragweed
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Ryegrass, Italian
0
0
0
0
0
0
0
0
0
0
40
20
0
0


Wheat
0
0
0
0
0
0
0
0
0
30
30
0
0
0











31 g ai/ha
Compounds





















Postemergence
1144
1145
1146
1147
1148
1149
1150
1161
1162
1163
1164
1165
1166
1167





Barnyardgrass
90
60
0
0
50
50
0
0
30
30
30
40
0
0


Blackgrass
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Corn
20
0
0
0
0
0
0
0
0
0
0
0
0
0


Foxtail, Giant
80
50
0
0
50
40
0
0
30
0
0
70
0
0



Galium

0
0
0
0
0
20
0
0
0
0
0
20
0
0



Kochia

50
0
0
0
0
0
0
0
0
0
0
30
0
0


Pigweed
0
0
0
0
0
0
0
0
0
0
0
10
0
0


Ragweed
20
0
0
0
0
0
0
0
0
0
0
0
0
0


Ryegrass, Italian
30
0
0
0
0
0
0
0
0
0
0
0
0
0


Wheat
30
0
0
0
0
0
0
0
0
0
0
0
0
0











31 g ai/ha
Compounds





















Postemergence
1168
1169
1170
1171
1172
1173
1174
1175
1176
1183
1184
1185
1186
1187





Barnyardgrass
0
30
0
20
0
50
70
50
80
80
70
20
100
20


Blackgrass
0
0
0
0
0
0
0
0
50
0
30
0
70
0


Corn
0
0
0
0
0
0
0
0
50
30
50
0
30
0


Foxtail, Giant
0
30
0
30
0
70
40
50
80
70
80
30
90
40



Galium

0
0
20
0
0
0
0
20
30
0
0
0
50
20



Kochia

0
0
0
0
0
30
0
0
0
0
0
0
20
0


Pigweed
0
0
0
0
0
30
0
0
0
0
0
0
0
0


Ragweed
0
0
0
0
0
0
0
0
0
0
0
0
20
0


Ryegrass, Italian
0
0
0
0
0
0
0
0
20
20
30
0
40
0


Wheat
0
0
0
0
0
0
0
0
50
20
40
0
30
0











31 g ai/ha
Compounds





















Postemergence
1188
1189
1190
1191
1192
1193
1237
1258
1259
1261
1262
1263
1264
1265





Barnyardgrass
70
70
0
0
50
0
0
30
30
90
70
0
0
80


Blackgrass
30
20
0
0
0
0
0
0
0
40
0
0
0
0


Corn
0
0
0
0
0
0
0
0
0
50
20
0
0
30


Foxtail, Giant
70
70
0
0
40
0
0
30
30
90
70
0
0
80



Galium

50
30
0
0
0
0
0
70
60
50
30
0
0
60



Kochia

0
0
0
0
0
0
0
0
0
20
20
0
0
50


Pigweed
0
0
0
0
0
0
0
0
40
0
30
0
0
30


Ragweed
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Ryegrass, Italian
0
0
0
0
0
0
0
0
0
20
0
0
0
0


Wheat
0
0
0
0
0
0
0
0
0
20
0
0
0
0











31 g ai/ha
Compounds





















Postemergence
1266
1267
1268
1269
1270
1271
1272
1273
1274
1275
1276
1277
1278
1279





Barnyardgrass
90
60
80
90
90
40
40
50
50
30
70
30
70
0


Blackgrass
20
0
0
0
0
0
20
0
0
0
0
0
0
0


Corn
90
0
0
0
0
30
0
0
30
0
0
0
0
0


Foxtail, Giant
80
60
50
60
60
20
50
60
50
20
30
50
50
0



Galium

50
0
0
0
60
60
50
40
50
0
0
0
0
0



Kochia

30
0
0
0
0
20
0
0
50
0
0
0
0
0


Pigweed
20
0
0
0
40
20
0
0
0
0
0
0
0
0


Ragweed
0
0
0
0
0
0
0
0
0
0
0
30
0
0


Ryegrass, Italian
20
0
0
0
0
0
20
0
0
0
0
0
0
0


Wheat
0
0
0
0
0
20
20
0
20
0
0
0
0
0











31 g ai/ha
Compounds





















Postemergence
1282
1283
1284
1285
1286
1287
1288
1289
1290
1291
1292
1293
1294
1295





Barnyardgrass
90
0
0
60
90
80
0
0
0
70
0
0
0
0


Blackgrass
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Corn
0
0
0
0
20
0
0
0
0
0
0
0
0
0


Foxtail, Giant
80
0
0
40
70
70
0
0
0
70
0
0
0
0



Galium

40
0
0
20
20
30
0
0
0
0
0
0
0
0



Kochia

0
0
0
0
0
0
0
0
0
0
0
0
0
0


Pigweed
0
0
0
20
0
0
0
0
0
0
0
0
0
0


Ragweed
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Ryegrass, Italian
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Wheat
0
0
0
0
0
0
0
0
0
0
0
0
0
0











31 g ai/ha
Compounds





















Postemergence
1296
1297
1333
1337
1338
1339
1340
1341
1342
1343
1344
1345
1346
1347





Barnyardgrass
0
0
0
20
70
70
20
40 
20
60
0
50
60
70


Blackgrass
0
0
0
0
0
0
0
0
0
0
0
0
30
30


Corn
0
0
0
0
0
0
0
0
0
0
0
0
0
30


Foxtail, Giant
0
0
0
20
50
70
0
0
20
60
0
20
60
70



Galium

0
0
0
0
0
30
0



0
0

70



Kochia

0
0
0
20
0
0
0
0
0
0
0
0
0
60


Pigweed
0
0
0
0
0
20
0
0
0
0
0
0
0
50


Ragweed
0
0
0
0
0
0
0
0
0
0
0
0
0
40


Ryegrass, Italian
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Wheat
0
0
0
0
0
0
0
0
0
0
0
0
30
20











31 g ai/ha
Compounds





















Postemergence
1348
1349
1350
1351
1352
1353
1354
1366
1367
1368
1369
1375
1393
1396





Barnyardgrass
90
70
60
0
60
40
0
20
0
20
20
70
70
70


Blackgrass
50
0
0
0
0
0
0
0
0
0
0
0
20
0


Corn
50
0
30
0
0
0
0
0
0
0
0
0
0
20


Foxtail, Giant
90
60
70
0
60
30
0
30
0
0
20
70
70
80



Galium

50
30




20
0
0
0
0
20
50
60



Kochia

0
0
50
0
0
0
0
0
0
0
0
30
30
60


Pigweed
0
0
30
0
0
0
0
0
0
0
20
0
40
30


Ragweed
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Ryegrass, Italian
20
0
20
0
0
0
0
0
0
20
0
0
0
20


Wheat
40
0
20
0
0
0
0
0
0
0
0
0
0
0













31 g ai/ha
Compounds














Postemergence
1397
1398
1399
1400
1402







Barnyardgrass
90
90
90
70
80



Blackgrass
40
20
20
30
0



Corn
50
0
0
20
0



Foxtail, Giant
80
90
70
70
50




Galium

20
30
40
20
60




Kochia

0
20
50
30
30



Pigweed
0
0
0
50
0



Ragweed
0
0
0
0
0



Ryegrass, Italian
50
0
20
30
0



Wheat
40
0
0
0
20














1000 g ai/ha
Compounds
















Preemergence
355
357
358
511
512
713
784







Barnyardgrass
0
0
0
90 
80 
0
80 



Corn
0
0
0


0




Crabgrass, Large
0
0
50 


80 




Foxtail, Giant
0
0
0
90 
90 
40 
90 




Kochia




0
0

0



Morningglory
0
0
0


0




Pigweed
0
0
0
0
0
0
0



Ragweed



0
0

0



Ryegrass, Italian



0
0

0



Velvetleaf
0
0
0


0




Wheat
0
0
0


0













500 g ai/ha
Compounds




















Preemergence
352
353
354
356
360
361
362
363
364
365
366
367
368





Barnyardgrass
0
0
0
0
0
0
0
0
0
0
0
0
90


Corn
0
0
0
0
0
0
0
0
0
0
0
0



Crabgrass, Large
0
0
0
0
0
0
0
0
0
0
0
0



Foxtail, Giant
0
0
0
0
0
0
0
0
0
0
0
0
90



Kochia













30


Morningglory
0
0
0
0
0
0
0

0
0
0
0



Pigweed
0
0
0
0
0
0
0
0
0
0
0
0
 0


Ragweed












60


Ryegrass, Italian












30


Velvetleaf
0
0
0
0
0
0
0
0
0
0
0
0



Wheat
0
0
0
0
0
0
0
0
0
0
0
0












500 g ai/ha
Compounds





















Preemergence
369
370
371
372
373
374
375
376
377
378
379
380
381
382





Barnyardgrass
90
90
90
90
90
90
90
90
90
90
30
90
20
50


Foxtail, Giant
90
90
90
90
90
90
90
90
90
100
40
90
30
30



Kochia

40
30
60
0
30
0
70
0
80
90
0
40
0
0


Pigweed
0
0
20
50
20
0
70
0
70
80
0
30
0
0


Ragweed
60
20
40
30
30
0
70
0
0
50
0
0
0
0


Ryegrass, Italian
20
0
20
30
40
30
50
20
60
80
0
20
0
0











500 g ai/ha
Compounds




















Preemergence
383
384
386
387
388
389
390
391
392
393
394
395
396





Barnyardgrass
90
0
80
80
80
70
80
90
90
90
80
0
90


Foxtail, Giant
70
0
90
90
90
90
90
90
90
90
90
0
90



Kochia

20
0
0
0
0
0
0
50
70
50
0
0
80


Pigweed
0
0
0
0
0
0
0
70
80
70
0
0
90


Ragweed
0
0

0
0
0
0
80
60
70
0
0
20


Ryegrass, Italian
20
0
50
0
0
0
0
50
80
50
0
0
70











500 g ai/ha
Compounds





















Preemergence
397
398
399
400
401
402
403
404
405
406
407
408
409
410





Barnyardgrass
90
90
90
100
90
90
90
90
90
90
80
0
80
60


Foxtail, Giant
90
90
90
100
90
90
90
90
90
90
90
0
90
80



Kochia

90
90
80
80
80
70
80
70
70
40
0
0
0
0


Pigweed
90
90
90
60
50
50
60
60
60
50
20
0
10
20


Ragweed
70
30
50
90
50
70
60
50
70
40
0
0
0
0


Ryegrass, Italian
70
70
60
40
40
40
70
80
30
50
0
0
0
0











500 g ai/ha
Compounds





















Preemergence
411
412
413
414
415
416
417
418
419
420
421
422
423
424





Barnyardgrass
80
70
0
0
0
0
0
0
90
90
90
70
0
90


Foxtail, Giant
90
70
0
10
0
50
0
0
90
90
90
70
0
90



Kochia

0
0
0
0
0
0
0
0
0
30
80
0
0
0


Pigweed
10
0
0
0
0
0
0
0
20
30
40
30
0
0


Ragweed
0
0
0
0
0
0
0
0
0
0
40
0
0
0


Ryegrass, Italian
0
0
0
0
0
0
0
0
0
0
30
0
0
0











500 g ai/ha
Compounds





















Preemergence
425
426
427
428
429
430
431
432
433
434
435
436
437
438





Barnyardgrass
20
80
90
90
90
90
90
40
90
90
90
100
90
100


Foxtail, Giant
70
90
90
90
100
90
100
0
90
100
90
100
100
100



Kochia

0
0
80
50
80
70
70
0
80
80
80
80
70
80


Pigweed
0
30
40
20
80
50
90
0
70
90
80
90
80
90


Ragweed
0
0
40
0

50
70
0
60
60
70
50
60
90


Ryegrass, Italian
0
0
30
30
80
50
70
0
60
90
20
60
50
70











500 g ai/ha
Compounds





















Preemergence
439
440
441
442
443
444
445
446
447
448
449
450
451
452





Barnyardgrass
90
100
90
90
90
90
90
90
90
90
90
90
0
90


Foxtail, Giant
100
100
90
90
90
90
90
90
90
90
90
90
0
90



Kochia

70
70
80
90
80
80
50
50
50
50
40
80
0
70


Pigweed
80
80
70
80
90
80
40
60
30
40
20
80
0
90


Ragweed
60
40
80
60
80
80
30
50
0
20
0
70
0
60


Ryegrass, Italian
50
50
80
80
50
90
90
60
30
20
0
40
0
30











500 g ai/ha
Compounds



















Preemergence
453
454
455
456
457
460
461
462
463
464
465
466





Barnyardgrass
90
80
90
0
0
80
90
90
80
90
100
90


Foxtail, Giant
90
90
90
0
0
90
90
90
90
90
100
90



Kochia

30
0
50
0
0
40
50
70
0
80
80
0


Pigweed
30
0
50
0
0
30
0
0
0
70
70
0


Ragweed
20
0
0
0
0
20
0
50
0

70
30


Ryegrass, Italian
0
30
0
0
0
60
20
0
20
90
70
20











500 g ai/ha
Compounds





















Preemergence
467
468
469
470
471
472
473
474
475
476
477
478
479
480





Barnyardgrass
90
20
90
90
90
90
100
90
90
90
90
60
30
0


Foxtail, Giant
100
80
90
90
90
90
100
90
90
100
90
80
90
90



Kochia

50
80
0
40
0
80
80
70
70
70
0
0
0
0


Pigweed
0
50
0
20
0
90
90
90
90
80
0
0
0
0


Ragweed
70
70
0

0
50
70
20
60
60
0
0
0
0


Ryegrass, Italian
20
0
0
30
0
80
90
50
40
40
0
0
0
0











500 g ai/ha
Compounds





















Preemergence
481
482
483
484
485
486
487
488
489
490
491
492
493
494





Barnyardgrass
10
10
70
40
80
70
90
90
90
90
90
90
90
90


Foxtail, Giant
90
80
90
90
90
90
90
90
90
90
90
90
90
90



Kochia

0
0
0
0
0
0
60
70
50
20
20
70
20
0


Pigweed
0
0
0
0
0
20
30
70
40
0
0
70
0
0


Ragweed
0
0
0
0
0
0
30
80
30
0
0
80
30
0


Ryegrass, Italian
0
0
30
0
0
20
40
70
20
50
30
50
20
0











500 g ai/ha
Compounds





















Preemergence
495
496
497
498
499
500
501
502
503
504
505
506
507
508





Barnyardgrass
90
90
90
90
90
40
90
60
90
90
0
90
80
90


Foxtail, Giant
90
90
90
80
90
90
90
90
90
90
0
90
50
70



Kochia

30
40
50
0
30
50
30
70
20
80
0
30
70
0


Pigweed
20
0
20
0
0
20
20
30
40
100
0
60
20
0


Ragweed
0
0
0
0
0
0
50
50
0
50
0
0
0
0


Ryegrass, Italian
20
0
30
0
0
0
0
30
50
70
0
50
0
0











500 g ai/ha
Compounds





















Preemergence
509
510
513
514
515
516
517
518
519
520
521
522
523
524





Barnyardgrass
90
80
90
90
0
80
0
60
90
90
90
90
90
40


Foxtail, Giant
70
70
90
90
70
90
30
90
100
90
90
90
90
70



Kochia

0
50
20
50
0
0
0
0
60
70
70
60
80
0


Pigweed
0
0
0
40
0
0
0
0
20
80
70
80
90
0


Ragweed
0
50
0
30
0
0
0
0
30
50
60
30
80
0


Ryegrass, Italian
0
10
30
60
0
0
0
0
70
50
50
60
90
0











500 g ai/ha
Compounds



















Preemergence
525
526
527
534
535
536
537
538
539
540
541
544





Barnyardgrass
50
20
20
0
0
0
0
0
90
90
90
80


Foxtail, Giant
70
80
80
0
0
20
0
0
90
90
90
90



Kochia

0
0
0
0
0
0
0
0
70
20
20
0


Pigweed
0
0
0
0
0
0
0
0
80
60
0
0


Ragweed
0
0
0
0
0
0
0
0
70

0
0


Ryegrass, Italian
0
0
0
0
0
0
0
0
50
40
20
0











500 g ai/ha
Compounds




















Preemergence
545
546
547
549
550
551
552
553
554
557
558
559
560





Barnyardgrass
70
90
90
80
90
90
90
90
90
0
100
100
100


Foxtail, Giant
90
90
90
90
90
90
90
90
90
0
100
100
100



Kochia

0
0
0
0
40
0
70
80
90
0
80
80
80


Pigweed
0
0
0
0
0
0
0
40
30
0
70
50
40


Ragweed
0
0
70
0
0
0
60

70
0
70
20
0


Ryegrass, Italian
0
0
0
0
20
0
40
70
40
0
60
50
70











500 g ai/ha
Compounds





















Preemergence
561
562
563
564
565
566
567
568
569
570
571
572
573
574





Barnyardgrass
90
90
100
100
90
100
100
100
100
100
90
90
100
90


Foxtail, Giant
90
90
100
100
90
100
100
100
100
100
100
90
100
90



Kochia

90
90
80
90
90
80
80
80
90
80
80
80
80
70


Pigweed
90
90
80
90
80
90
40
60
80
70
80
80
80
50


Ragweed
80
80
60
90
50
90
60
50
70
0
0
50
50
0


Ryegrass, Italian
40
90
0
90
40
70
80
100
70
90
80
50
90
80











500 g ai/ha
Compounds





















Preemergence
575
576
577
587
588
589
590
591
592
593
594
595
596
597





Barnyardgrass
100
90
100
90
90
90
90
90
90
90
90
90
100
70


Foxtail, Giant
100
90
100
90
90
90
90
90
90
90
90
90
100
80



Kochia

70
90
70
0
0
0
20
60
30
0
50
50
70
20


Pigweed
40
80
40

0
0
 0
40
0
0
20
30
40
0


Ragweed
0
60
40
0
0
0

60
20
0
20
30
20
0


Ryegrass, Italian
80
30
80
60
50
40
30
60
50
50
90
40
50
0











500 g ai/ha
Compounds



















Preemergence
598
599
600
601
602
605
606
607
608
609
610
611





Barnyardgrass
60
30
90
80
0
70
80
30
80
90
90
90


Foxtail, Giant
60
0
90
80
0
90
90
90
90
90
90
90



Kochia

0
0
20
0
0
0
0
0
70
60
70
60


Pigweed
0
0
0
0
0
0
0
0
70
80
80
80


Ragweed
0
0
0
0
0
0
0
0
60
60
70



Ryegrass, Italian
20
0
0
0
0
20
0
0
50
60
70
60











500 g ai/ha
Compounds




















Preemergence
612
613
614
616
617
618
619
620
621
622
623
624
625





Barnyardgrass
90
90
90
90
90
90
0
80
90
90
90
90
90


Foxtail, Giant
90
90
90
100
100
100
0
90
90
90
90
90
90



Kochia

20
70
20
80
70
90
20
20
40
80
70
60
80


Pigweed
70
70
0
90
90
90
0
0
20
80
80
80
90


Ragweed
50
60
0
80
60
70
0
0
90
60
80
70
60


Ryegrass, Italian
70
80
20
90
90
90
0
0
40
40
90
40
50











500 g ai/ha
Compounds

















Preemergence
630
631
632
633
634
635
636
637
638
639





Barnyardgrass
90
0
90
90
70
90
90
90
90
90


Foxtail, Giant
90
0
90
90
80
90
90
100
100
100



Kochia

50
0
70
50
0
60
70
60
20
80


Pigweed
0
0
70
50
30
70
80
100
60
80


Ragweed
30
0
70
50
0
50
70
70
60
70


Ryegrass, Italian
20
0
70
60
0
30
90
90
90
90











500 g ai/ha
Compounds





















Preemergence
640
641
642
643
644
645
646
647
648
649
650
651
652
653





Barnyardgrass
90
0
90
90
90
90
90
90
90
90
100
90
90
90


Foxtail, Giant
90
100
90
100
90
90
100
100
80
70
100
100
100
100



Kochia

60
50
60
40
80
60
70
0
50
70
70
70
30
70


Pigweed
90
50
60
20
70
50
70
60
40
60
90
100
30
90


Ragweed
60
60
50
20
60
20
70
40
20
70
80
90
0
80


Ryegrass, Italian
50
60
80
90
90
60
90
30
40
70
90
90
60
70











500 g ai/ha
Compounds





















Preemergence
654
655
656
657
658
659
660
661
662
663
664
665
666
667





Barnyardgrass
90
90
90
90
90
90
90
90
90
100
90
90
90
90


Foxtail, Giant
90
90
90
90
90
90
90
100
100
100
100
100
100
100



Kochia

40
40
50
40
30
0
0
70
90
80
70
70
60
70


Pigweed
70
60
40
30
50
0
0
40
80
70
60
30
20
50


Ragweed
30
30
60
20
70
0
0
80
80
70
80
90
70
70


Ryegrass, Italian
80
60
60
30
70
30
20
50
90
90
80
50
50
90













500 g ai/ha
Compounds


















Preemergence
668
674
675
676
677
678
679
680
681







Barnyardgrass
90
80
80
90
90
90
90
90
80



Foxtail, Giant
100
90
90
90
90
90
90
90
90




Kochia

70
30
0
0
40
30
60
20
60



Pigweed
50
0
0
0
0
0
40
0
30



Ragweed
40
0
0
0
0
0
30
0
0



Ryegrass, Italian
0
0
20
20
40
20
30
20
30












500 g ai/ha
Compounds





















Preemergence
682
683
684
685
686
687
688
689
690
691
692
693
694
695





Barnyardgrass
0
60
90
80
90
90
90
90
90
90
90
90
90
90


Foxtail, Giant
90
90
90
90
90
90
90
90
90
90
90
90
90
90



Kochia

0
20
0
0
40
40
50
60
90
90
80
90
0
90


Pigweed
0
0
0
0
20
30
40
40
90
80
90
80
0
40


Ragweed
0
0
0
0
0
0
40
30
80
90
70
60
0
40


Ryegrass, Italian
30
0
20
30
20
20
20
20
70
60
60
70
10
30











500 g ai/ha
Compounds


















Preemergence
696
697
698
699
700
701
702
703
704
705
706





Barnyardgrass
90
90
90
90
90
90
90
80
90
0
70


Foxtail, Giant
90
90
90
90
90
90
90
90
90
0
80



Kochia

60
80
40
70
70
0
20

30
0
0


Pigweed
30
50
50
50
60
0
30
0
30
0
0


Ragweed
40
60
50
70
60
0
0
0
20
0
0


Ryegrass, Italian
60
50
60
40
30
0
0
0
20
0
0














500 g ai/ha
Compounds















Preemergence
711
712
714
715
716







Barnyardgrass
0
0
0
0
0



Corn


0
0
0



Crabgrass, Large


30 
0
0



Foxtail, Giant
0
0
20 
0
0




Kochia

0
0






Morningglory


0
0
0



Pigweed
0
0
0
0
0



Ragweed
0
0






Ryegrass, Italian
0
0






Velvetleaf


0
0
0



Wheat


0
0
0












500 g ai/ha
Compounds





















Preemergence
717
718
719
720
721
722
723
724
725
726
727
728
729
730





Barnyardgrass
90
90
90
100 
80
80 
0
0
90
90
90 
90
0
100 


Corn
















Crabgrass, Large
















Foxtail, Giant
90
90
90
90
90
80 
50 
0
90
90
90 
90
0
100 



Kochia

60
60
80
70
 0
0
0
0
50
90
0
90
0
80


Morningglory
















Pigweed
30
 0
90
 0
 0
0
0
0
 0
90
0
 0
0
50


Ragweed
40
40
70
80
50
0
0
0
 0
50
0
30
0
60


Ryegrass, Italian
30
30
90
20
20
0
0
0
20
80
0
60
0
70


Velvetleaf
















Wheat

























500 g ai/ha
Compounds





















Preemergence
731
732
733
734
735
736
737
738
739
740
741
742
743
744





Barnyardgrass
90
100 
100 
100 
90
90
80
100 
100 
90
0
90
90
90


Corn
















Crabgrass, Large
















Foxtail, Giant
90
90
90
100 
90
90
90
100 
100 
100 
0
90
90
90



Kochia

60
90
80
90
80
70
50
70
80
90
30 
90
80
90


Morningglory
















Pigweed
 0
20
60
80
20
20
 0
50
30
80
40 
50
20
50


Ragweed
70
70
80
50
 0
20
 0
70
80
50
0
80
40
50


Ryegrass, Italian
40
80
60
90
90
90
70
20
30
80
0
90
90
80


Velvetleaf
















Wheat

























500 g ai/ha
Compounds





















Preemergence
745
746
747
748
749
750
751
752
753
754
755
756
757
758





Barnyardgrass
90
 0
70
30 
20
90 
90
90
100 
100 
0
100 
90
100 


Corn
















Crabgrass, Large
















Foxtail, Giant
90
90
90
90 
90
90 
90
90
90
90 
0
100 
90
100 



Kochia

90
60
80
0
20
0

70
20
0
0
70
70
60


Morningglory
















Pigweed
90
20
50
0
 0
0
 0
40
 0
0
0
70
70
20


Ragweed
80
 0
 0
0
 0
0
40
60
 0
0
0
30
90
 0


Ryegrass, Italian
90
40
60
0
20
20 
20
30
20
0
0
70
60
70


Velvetleaf
















Wheat

























500 g ai/ha
Compounds





















Preemergence
759
760
761
762
763
764
765
766
767
768
769
771
772
773





Barnyardgrass
100 
100 
100 
100 
80
100 
100 
90 
90 
90
100 
90
40 
0


Corn
















Crabgrass, Large
















Foxtail, Giant
100 
100 
90
100 
50
80 
80
40 
90 
90
100 
90
90 
0



Kochia

20
60 
80
50
30
0
 0
0
0
70
70
80
30 
0


Morningglory
















Pigweed
 0
0
 0
 0
30
0
 0
0
0
20
80
 0
0
0


Ragweed
 0
0
 0
50
 0
0
30
0
0
 0
70
50
0
0


Ryegrass, Italian
20
0
40
70
 0
20 
60
0
0
20
40
70
0
0


Velvetleaf
















Wheat

























500 g ai/ha
Compounds





















Preemergence
774
775
776
777
778
779
780
781
782
783
785
786
787
788





Barnyardgrass
0
100 
90
100 
90
90
90
100 
90
70 
90
90 
70
90


Corn
















Crabgrass, Large
















Foxtail, Giant
0
100 
100 
100 
90
90
90
100 
100 
80 
90
90 
90
100 



Kochia

0
80
60
 0
80
80
80
90
90
50 
40
0
90
80


Morningglory
















Pigweed
0
70
60
40
80
60
50
70
50
0
20
0
80
90


Ragweed
0
80
80
 0
60
70
70
 0
20
0
 0
0
70
90


Ryegrass, Italian
0
 0
50
70
20
40
20
50
60
0
40
0
 0
40


Velvetleaf
















Wheat

























500 g ai/ha
Compounds





















Preemergence
789
790
791
815
816
817
818
819
820
821
822
823
824
825





Barnyardgrass
90
90
90
100 
90
90
100 
100
100 
90
100 
100 
100 
90


Corn
















Crabgrass, Large
















Foxtail, Giant
90
90
90
100 
90
90
100 
100
100 
100 
100 
100 
100 
90



Kochia

30
80
60
80
80
70
80
100
80
90
80
70
70
60


Morningglory
















Pigweed
20
40
 0
50
60
80
60
 30
70
50
50
50
40
30


Ragweed
 0
60
40
 0
50
50
 0
 20
60
 0
30
40
50
20


Ryegrass, Italian
 0
70
20
80
80
40
90
100
80
90
40
60
40
40


Velvetleaf
















Wheat

























500 g ai/ha
Compounds





















Preemergence
826
827
828
829
830
831
832
833
834
835
836
837
838
839





Barnyardgrass
100 
90
90
90
90
70
80
90
90
100 
90
90
90
90


Corn
















Crabgrass, Large
















Foxtail, Giant
100 
90
100 
90
90
90
80
100 
100 
100 
90
90
90
90



Kochia

90
60
40
90
90
 0
100 
80
90
90
90
90
80
90


Morningglory
















Pigweed
60
40
 0
60
40
20
30
 0
30
40
60
80
90
90


Ragweed
80
20
 0
70
20
 0
60
20
20
 0
 0
70
60
90


Ryegrass, Italian
80
70
70
40
30
50
30
80
80
70
80
70
60
40


Velvetleaf
















Wheat

























500 g ai/ha
Compounds





















Preemergence
840
841
842
843
844
845
846
847
848
849
850
851
852
853





Barnyardgrass
90
100 
90
80
20 
90
90
60 
90
90
90
90
90
100 


Corn
















Crabgrass, Large
















Foxtail, Giant
90
90
100
90
30 
90
90
50 
90
90
90
90
90
100 



Kochia

70
60
80
70
0
90
70
0
70
80
70
70
20
40


Morningglory
















Pigweed
60
30
70
40
0
 0
 0
0
50
50
30
90
40
40


Ragweed
 0
 0
80
30
0
 0
 0
0
30
90
 0
30
 0
20


Ryegrass, Italian
20
40
60
50
0
30
70
0
50
90
70
70
30
60


Velvetleaf
















Wheat

























500 g ai/ha
Compounds





















Preemergence
854
855
856
857
858
859
860
861
862
864
865
866
867
868





Barnyardgrass
80 
100 
90
90
90
90
90
90
100 
90
70 
90
90
60 


Corn
















Crabgrass, Large
















Foxtail, Giant
80 
90
90
90
90
90
90
90
90
90
80 
90
90
60 



Kochia

0
30
50
30
70
60
60
60
70
80

80
70
0


Morningglory
















Pigweed
0

50
70
50
80
90
70
90
90
0
50
30
0


Ragweed
0
 0
20
30
30
50
50
70
100 
50
0
30
30
0


Ryegrass, Italian
0
30
80
60
70
80
40
90
20
50
0
70
60
0


Velvetleaf
















Wheat

























500 g ai/ha
Compounds





















Preemergence
869
870
871
872
873
874
875
876
877
878
879
880
881
882





Barnyardgrass
90 
80 
90
100 
90
100 
90
90
100 
100 
100 
100 
90
90


Corn
















Crabgrass, Large
















Foxtail, Giant
90 
50 
80
90
100 
100 
90
100 
90
100 
100 
100 
90
90



Kochia

0
0
80
80
90
90
80
70
80
90
90
90
60
90


Morningglory
















Pigweed
0
0
30
60
50
30
 0
30
 0
40
80
90
 0
20


Ragweed
0
0
20
100 
90
60
50
80
60
80
90
80
 0
60


Ryegrass, Italian
0
0
30
40
80
50
30
30
20
70
90
70
60
30


Velvetleaf
















Wheat

























500 g ai/ha
Compounds





















Preemergence
883
885
886
887
888
889
890
891
892
893
894
895
896
897





Barnyardgrass
90
90
90
90
90
90
90
80
100 
100 
100 
100 
90
90


Corn
















Crabgrass, Large
















Foxtail, Giant
90
80
100 
90
90
90
90
90
100 
90
100 
90
100 
100 



Kochia

60
 0
90
20
80
80
90
20
90
90
90
90
50
90


Morningglory
















Pigweed
 0
 0
 0
 0
 0
 0
50
 0
40
50
50
50
40
60


Ragweed
 0
 0
50
 0
 0
40
 0
 0
50
70
40
 0
 0
60


Ryegrass, Italian
20
20
60
 0
60
40
70
30
90
90
60
70
70
50


Velvetleaf
















Wheat

























500 g ai/ha
Compounds





















Preemergence
898
899
900
901
902
903
904
905
906
907
908
909
910
911





Barnyardgrass
90
90
90
90
90
90
90
90
0
80
50 
80
100 
100 


Corn
















Crabgrass, Large
















Foxtail, Giant
90
90
90
90
90
90
90
90
0
90
80 
90
100 
100 



Kochia

90
70
90
80
 0
90
90
90
0
20
0
50
90
100 


Morningglory
















Pigweed
80
40
90
60
 0
 0
50
 0
0
 0
0
 0
30
50


Ragweed
60
60
80
 0
 0
 0
 0
 0
0
 0
0
20
 0
60


Ryegrass, Italian
70
20
60
50
20
 0
 0
 0
0
 0
0
30
60
90


Velvetleaf
















Wheat

























500 g ai/ha
Compounds





















Preemergence
912
913
914
915
916
917
918
919
920
921
922
923
924
925





Barnyardgrass
90
90
90
100 
80
80 
40 
0
90 
90
80
70 
90
90


Corn
















Crabgrass, Large
















Foxtail, Giant
100 
90
90
100 
80
90 
70 
0
90 
100 
90
70 
90
90



Kochia

70
40
60
90
60
0
0
0
0
30
 0
0
 0
 0


Morningglory
















Pigweed
 0
 0
90
90
20
0
0
0
0
 0
 0
0
 0
 0


Ragweed
 0
60
 0
90
70
0
0
0
0
 0
 0
0
 0
 0


Ryegrass, Italian
50
40
60
70
30
0
0
0
0
60
40
0
70
30


Velvetleaf
















Wheat

























500 g ai/ha
Compounds





















Preemergence
926
927
928
929
930
931
932
933
934
935
936
937
938
939





Barnyardgrass
90 
70 
90
90
90
90
90
100 
90
90
90
90
90
90


Corn
















Crabgrass, Large
















Foxtail, Giant
90 
70 
90
90
90
90
100 
100 
90
90
90
90
90
90



Kochia

0
0
80
90
90
90
70
90
80
80
90
80
80
60


Morningglory
















Pigweed
0
0
20
50
30
40
30
30
80
20
80
80
90
 0


Ragweed
0
0
 0
30
 0
30
30
90
30
30
50
80
20
50


Ryegrass, Italian
0
0
70
80
70
70
60
70
60
50
70
50
30
20


Velvetleaf
















Wheat

























500 g ai/ha
Compounds





















Preemergence
940
941
942
943
944
945
946
947
948
949
950
951
952
953





Barnyardgrass
70 
90
90
90
90
90 
80
60
90 
100 
100 
90
90
90


Corn
















Crabgrass, Large
















Foxtail, Giant
90 
90
90
90
90
70 
20
80
90 
70 
90
70
90
100 



Kochia

0
 0
90
80
70
0
50
40
0
50 
60
20
30
60


Morningglory
















Pigweed
0
 0
90
50
20
0
 0
 0
0
0
 0
 0
 0
 0


Ragweed
0
30
50
30
50
0
 0
 0
0
0
20
 0
 0
 0


Ryegrass, Italian
0
 0
20
50
 0
0
 0
 0
0
0
70
 0
 0
60


Velvetleaf
















Wheat

























500 g ai/ha
Compounds





















Preemergence
954
955
956
957
958
959
960
961
962
963
964
965
966
967





Barnyardgrass
90 
100 
100 
100 
90
100 
90
90
90
100 
90
90
90
90 


Corn
















Crabgrass, Large
















Foxtail, Giant
90 
100 
100 
70
90
100 
90
90
90
100 
90
90
90
90 



Kochia

20 
70
90
80
90
90
30
90
70
70
20
60
30
0


Morningglory
















Pigweed
0
 0
 0
20
30
30
 0
30
50
30
 0
 0
 0
0


Ragweed
0
30
80
30
60
70
 0
90
30
 0
 0
 0
 0
0


Ryegrass, Italian
0
60
90
40
20
60
 0
80
30
40
30
90
60
0


Velvetleaf
















Wheat

























500 g ai/ha
Compounds





















Preemergence
968
969
973
974
975
976
977
978
979
980
981
982
983
984





Barnyardgrass
60 
80 
90
100 
100 
100 
90
90
90
100 
100 
90
100 
100 


Corn
















Crabgrass, Large
















Foxtail, Giant
60 
90 
90
90
90
90
90
90
100 
100 
100 
100 
100 
100 



Kochia

0
0
60
100 
90
90
90
90
90
90
90
90
90
90


Morningglory
















Pigweed
0
0
 0
60
90
50
70
50
90
 0
 0
50
40
60


Ragweed
0
0
70
90
90
90
100 
90
90
20
50
80
100 
30


Ryegrass, Italian
0
30 
30
90
40
80
40
90
60
30
60
90
60
30


Velvetleaf
















Wheat

























500 g ai/ha
Compounds





















Preemergence
985
986
987
988
989
990
991
992
993
994
995
996
998
999





Barnyardgrass
0
90
90
90
90
100 
90
0
90
100
90
0
0
90


Corn
















Crabgrass, Large
















Foxtail, Giant
0
100 
90
90
90
100 
90
0
90
100
90
0
0
90



Kochia

0
70
60
80
90
90
60
0
50
 60
 0
0
0
20


Morningglory
















Pigweed
0
70
20
40
 0
80
50
0
80
 70
30
0
0
50


Ragweed
0
70
 0
80
40
80
30
0
60
 0
20
0
0
30


Ryegrass, Italian
0
80
40
20
 0
60
50
0
90
100
50
0
0
50


Velvetleaf
















Wheat

























500 g ai/ha
Compounds





















Preemergence
1000
1001
1002
1013
1014
1015
1016
1017
1018
1019
1020
1021
1022
1023





Barnyardgrass
60
0
70
90
90
90
90 
90
90
0
90
100 
100 
90


Corn
















Crabgrass, Large
















Foxtail, Giant
90
0
80
90
90
90
90 
90
90
0
90
100 
100 
90



Kochia

 0
0
 0
70
70
60
0
70
60
0
20
90
80
 0


Morningglory
















Pigweed
40
0
50
40
30
40
0
60
80
0
40
80
70
30


Ragweed
 0
0
 0
 0
 0
50
0
90
40
0
20
70
 0
40


Ryegrass, Italian
20
0
 0
70
70
90
0
70
70
0
30
20
50
70


Velvetleaf
















Wheat

























500 g ai/ha
Compounds





















Preemergence
1024
1025
1026
1027
1028
1029
1030
1031
1032
1033
1034
1035
1036
1037





Barnyardgrass
90
70
90
90
90
90
90
0
70 
90
90
90
90
90


Corn
















Crabgrass, Large
















Foxtail, Giant
90
90
90
90
90
90
90
0
70 
90
90
90
90
80



Kochia

40
20
80
90
60
90
70
0
0
60
70
50
90
90


Morningglory
















Pigweed
50
50
 0
40
 0
 0
 0
0
0
 0
 0
 0
 0
20


Ragweed
30
 0
50
80

 0
 0
0
0
10
90
70
50
60


Ryegrass, Italian
90
30
 0
 0
30
90
70
0
0
50
60
70
20
70


Velvetleaf
















Wheat

























500 g ai/ha
Compounds





















Preemergence
1038
1039
1040
1041
1042
1043
1044
1045
1046
1047
1048
1049
1053
1054





Barnyardgrass
100 
100 
90
60
90
90
90
90
90
80
90
70
60 
0


Corn
















Crabgrass, Large
















Foxtail, Giant
100 
100 
90
90
90
90
90
90
90
80
90
90
0
0



Kochia

80
100 
80

70
70
50
20
70
80
90
70
0
0


Morningglory
















Pigweed
30
40
40
20
50
20
30
 0
 0
20
90
60
0
0


Ragweed
70
90
80

40
50
30
30
70
60
80
40
0
0


Ryegrass, Italian
70
80
50
 0
50
50
50
70
60
 0
40
30
0
0


Velvetleaf
















Wheat

























500 g ai/hae
Compounds





















Preemergence
1055
1056
1057
1058
1059
1073
1094
1095
1096
1097
1098
1099
1100
1101





Barnyardgrass
0
90 
0
100 
90
100 
80 
60 
0
0
90
90
90
90


Corn
















Crabgrass, Large
















Foxtail, Giant
0
90 
0
100 
80
100 
100 
90 
0
0
90
90
90
90



Kochia

0
0
0
30
20
70
0
0
0
0
70
70
60
70


Morningglory
















Pigweed
0
0
0
 0
 0
100 
0
30 
0
0
 0
30
 0
20


Ragweed
0
0
0
 0
30
30
0
0
0
0
 0
60
 0
40


Ryegrass, Italian
0
0
0
40
 0
20
0
0
0
0
50
70
30
70


Velvetleaf
















Wheat

























500 g ai/ha
Compounds





















Preemergence
1102
1111
1112
1113
1114
1115
1116
1117
1118
1119
1120
1121
1122
1123





Barnyardgrass
90
0
0
0
90
90
90
90
90
90
100 
100
90
90


Corn
















Crabgrass, Large
















Foxtail, Giant
90
0
0
0
90
90
90
90
90
80
100 
100
90
90



Kochia

70
0
0
0
60
70
30
70
70
80
70
100
70
80


Morningglory
















Pigweed
50
0
0
0
 0
40
20
 0
 0
30
50
 50
70
50


Ragweed
50
0
0
0
 0
20
20
70
60
70
50
100
80
60


Ryegrass, Italian
60
20 
0
0
20
60
20
60
50
30
40
 60
90
60


Velvetleaf
















Wheat

























500 g ai/ha
Compounds





















Preemergence
1124
1125
1126
1127
1128
1129
1130
1131
1132
1133
1134
1135
1136
1137





Barnyardgrass
90
90
90
30 
90
90
0
90
90 
90
80
0
90
0


Corn
















Crabgrass, Large
















Foxtail, Giant
90
100 
90
70 
90
90
30 
90
100 
90
90
0
90
0



Kochia

90
80
80
0
80
50
0
90
0
100 
60
0
80
0


Morningglory
















Pigweed
70
40
60
0
 0
 0
0
90
0
70
30
0
 0
0


Ragweed
60

50
0
50
 0
0
80
0
60
70
0
 0
0


Ryegrass, Italian
30
60
70
0
40
50
0
70
50 
30
40
0
30
0


Velvetleaf
















Wheat

























500 g ai/ha
Compounds





















Preemergence
1138
1139
1140
1151
1152
1153
1154
1155
1156
1157
1158
1159
1160
1177





Barnyardgrass
90
90
100 
100 
90
90
90
100 
90
90
100 
90 
90
100 


Corn
















Crabgrass, Large
















Foxtail, Giant
90
90
100 
100 
90
90
90
90
100 
100 
100 
90 
90
100 



Kochia

80
60
80
80
 0
70
90
90
80
90
30
30 
50
30


Morningglory
















Pigweed
 0
 0
40
100 
80
 0
80
30
20
60
 0
0
20
20


Ragweed
 0
50
60
60
 0
 0
90
80
100 
80
 0
0
 0
30


Ryegrass, Italian
50
70
40
70
20
50
50
30
30
90
70
0
 0
70


Velvetleaf
















Wheat

























500 g ai/ha
Compounds





















Preemergence
1178
1179
1180
1181
1182
1194
1195
1196
1197
1198
1199
1200
1201
1202





Barnyardgrass
50
0
70 
0
0
30 
80 
90 
100
100
100 
0
70
90


Corn
















Crabgrass, Large
















Foxtail, Giant
70
0
50 
0
0
20 
40 
90 
100
100
100 
0
80
90



Kochia

70
0
30 
0
0
0
0
0
100
 80
 0
0
70
60


Morningglory
















Pigweed
50
0
0
0
0
0
0
0
 80
100
60
0
70
 0


Ragweed
50
0
0
0
0
0
0
0
100
100
90
0
70
90


Ryegrass, Italian
20
0
0
0
0
0
0
0
 70
 60
 0
0
 0
60


Velvetleaf
















Wheat

























500 g ai/ha
Compounds





















Preemergence
1203
1204
1205
1206
1207
1208
1209
1210
1211
1212
1213
1214
1215
1216





Barnyardgrass
90
90
90
100 
100 
100
90
100 
100 
100 
100 
90
100 
90


Corn
















Crabgrass, Large
















Foxtail, Giant
90
90
100 
90
100 
100
100 
100 
100 
100 
100 
90
90 
80



Kochia

50
80
30
100 
90
100
90
10
70
100 
80
60
90 



Morningglory
















Pigweed
20
100 
30
90
60
 90
 0
 0
70
90
80
70
0
 0


Ragweed
80
90
 0
60
90
100
90
 0
50
90
70
70
0
20


Ryegrass, Italian
20
90
70
 0
20
 70
50
50
80
70
70
90
0
 0


Velvetleaf
















Wheat

























500 g ai/ha
Compounds





















Preemergence
1217
1218
1219
1220
1221
1222
1223
1224
1225
1226
1227
1228
1229
1230





Barnyardgrass
100 
100 
90 
90
100 
20
90
80
90
100 
40
90
100 
50


Corn
















Crabgrass, Large
















Foxtail, Giant
100 
90 
90 
90
100 
60
90
90
90
100 
90
90
100 
90



Kochia

0
0
0
50
50
40
20
 0
70
70
 0
 0
90
90


Morningglory
















Pigweed
0
0
0
40
50
 0
 0
70
50
90
60
60
90
30


Ragweed
0
0
0
40
70
 0
20
20
60
30
 0
 0
70
 0


Ryegrass, Italian
0
0
0
50
80
 0
 0
20
40
80
70
60
40
 0


Velvetleaf
















Wheat

























500 g ai/ha
Compounds





















Preemergence
1231
1232
1233
1234
1235
1236
1238
1239
1240
1241
1242
1243
1244
1245





Barnyardgrass
90
90
90
100 
100 
100 
90
90
0
0
60 
0
90 
80


Corn
















Crabgrass, Large
















Foxtail, Giant
90
90
90
100 
100 
100 
90
90
0
0
80 
0
90 
90



Kochia

90
80
70
80
80
90
60

0
0
0
0
0
20


Morningglory
















Pigweed
70
90
40
90
90
90
60
60
0
0
0
0
0
 0


Ragweed
60
80
50
60
90
30
50
70
0
0
0
0
0
20


Ryegrass, Italian
90
60
70
80
60
80
50
50
0
0
0
0
50 
60


Velvetleaf
















Wheat

























500 g ai/ha
Compounds





















Preemergence
1246
1247
1248
1249
1250
1251
1252
1253
1254
1255
1256
1257
1260
1280





Barnyardgrass
80
90
90 
100
100 
100 
100 
100 
100 
100 
100 
0
100 
50 


Corn
















Crabgrass, Large
















Foxtail, Giant
70
80
50 
100
100 
100 
100 
100 
100 
100 
100 
0
90
80 



Kochia

80
30
0
 90
40
90
80
80
70
80
70
0
90
0


Morningglory
















Pigweed
 0
 0
0
 90
30
90
90
80
70
90
70
0
90
30 


Ragweed
60
 0
0
 70
 0
80
70
60
30
70
30
0
90
0


Ryegrass, Italian
50
20
0
100
50
60
90
60
40
40
60
0
60
0


Velvetleaf
















Wheat

























500 g ai/ha
Compounds





















Preemergence
1281
1298
1299
1300
1301
1302
1303
1304
1305
1306
1307
1308
1309
1310





Barnyardgrass
90
90
90
90
90
90
30 
0
90 
90
90
90
90
90


Corn
















Crabgrass, Large
















Foxtail, Giant
90
90
90
90
90
90
90 
0
90 
90 
90
90
90
90



Kochia

60
80
70
60
60
60
0
0
0
70 
90
50
60
70


Morningglory
















Pigweed
40
 0
60
40
30
30
30 
0
0
0
 0
20
20
40


Ragweed
60
20
70
80
20
50
0
0
0
60 
60
70
50
40


Ryegrass, Italian
20
 0
70
60
 0
 0
0
0
0
0
 0
 0
20
70


Velvetleaf
















Wheat

























500 g ai/ha
Compounds





















Preemergence
1311
1312
1313
1314
1316
1317
1318
1319
1320
1321
1323
1324
1325
1326





Barnyardgrass
100 
100 
100 
100 
90
90
90
90
60 
100 
90
100 
90
90


Corn
















Crabgrass, Large
















Foxtail, Giant
100 
100 
80 
100 
90
100 
90
90
80 
100 
90
100 
90
90



Kochia

100 
80
100 
80
80
80
80
80
60 
80
90
90
90
100 


Morningglory
















Pigweed
20
60
0
70
80
60
80
60
0
 0
40
40
90
 0


Ragweed
90
100 
0
100 
70
40
90
20
0
50
70
90
70
 0


Ryegrass, Italian
80
70
0
40
90
90
60
90
0
40
70
60
 0
20


Velvetleaf
















Wheat

























500 g ai/ha
Compounds





















Preemergence
1327
1328
1329
1330
1331
1332
1334
1335
1336
1355
1356
1357
1358
1359





Barnyardgrass
90
90
100 
90
90 
90 
80
0
0
0
0
0
0
0


Corn









0
0
0
0
0


Crabgrass, Large









0
0
0
80 
20 


Foxtail, Giant
90
90
90
90
100 
90 
80
0
0
0
0
0
0
0



Kochia

90
50
50
90
0
0
20
0
0







Morningglory









0
0
0

0


Pigweed
30
 0
30
 0
0
0
30
0
0
0
0
0
0
0


Ragweed
 0
 0
20
50
0
0
30
0
0







Ryegrass, Italian
20
30
40
50
80 
0
20
0
0







Velvetleaf









0
0
0
0
0


Wheat









0
0
0
50 
0











500 g ai/ha
Compounds





















Preemergence
1360
1361
1362
1370
1371
1372
1373
1374
1376
1377
1378
1379
1380
1381





Barnyardgrass
0
0
0
90
100 
100 
100
0
100 
100 
90
100 
100 
100 


Corn
0
0
0













Crabgrass, Large
0
0
0













Foxtail, Giant
0
0
0
90
90
100 
100
0
100 
100 
90
100 
100 
100 



Kochia




80
90
90
100
0
0
80
90
90
90
80


Morningglory
0
0
0













Pigweed
0
0
0
20
90
90
100
0
0
40
70
90
90
100 


Ragweed



80
80
90
100
0
0
30
90
90
80
80


Ryegrass, Italian



90
50
60
 90
0
70 
50
90
50
50
50


Velvetleaf
0
0
0













Wheat
0
0
0






















500 g ai/ha
Compounds




















Preemergence
1382
1383
1384
1385
1386
1387
1388
1389
1390
1391
1392
1394
1395





Barnyardgrass
70
100 
90
90
100 
90
100 
100 
90
100 
60 
90
90


Corn















Crabgrass, Large















Foxtail, Giant
90
100 
90
90
90
90
100 
100 
90
100 
60 
90
90



Kochia

60
90
70
20
90
60
90
90
90
90
0
60
 0


Morningglory















Pigweed
20
80
30
 0
90
60
70
80
90
90
0
30
 0


Ragweed
 0
80
 0
 0
80
 0
70
30
70
90
0
80
 0


Ryegrass, Italian
 0
70
70
 0
70
 0
100 
90
30
70
0
60
40


Velvetleaf















Wheat
























125 g ai/ha
Compounds




















Preemergence
352
353
354
356
360
361
362
363
364
365
366
367
368





Barnyardgrass
0
0
0
0
0
0
0
0
0
0
0
0
90 


Corn
0
0
0
0
0
0
0
0
0
0
0
0



Crabgrass, Large
0
0
0
0
0
0
0
0
0
0
0
0



Foxtail, Giant
0
0
0
0
0
0
0
0
0
0
0
0
90 



Kochia













0


Morningglory
0
0
0
0
0
0
0

0
0
0
0



Pigweed
0
0
0
0
0
0
0
0
0
0
0
0
0


Ragweed












30 


Ryegrass, Italian












0


Velvetleaf
0
0
0
0
0
0
0
0
0
0
0
0



Wheat
0
0
0
0
0
0
0
0
0
0
0
0












125 g ai/ha
Compounds





















Preemergence
369
370
371
372
373
374
375
376
377
378
379
380
381
382





Barnyardgrass
90
90
90
90
90
90
90
90
90
20
0
70
0
0


Foxtail, Giant
90
90
90
80
80
90
90
90
90
90
0
50
0
0



Kochia

50
0
20
0
0
0
20
0
50
80
0
0
0
0


Pigweed
0
0
0
0
0
0
20
0
50
60
0
0
0
0


Ragweed
60
0
30
0
0
0
0
0
0
10
0
0
0
0


Ryegrass, Italian
0
0
0
0
30
0
20
0
20
50
0
0
0
0











125 g ai/ha
Compounds




















Preemergence
383
384
386
387
388
389
390
391
392
393
394
395
396





Barnyardgrass
50
0
80
70
60
70
60
80
90
90
40
0
90


Foxtail, Giant
50
0
80
70
80
80
80
90
90
90
70
0
90



Kochia

0
0
0
0
0
0
0
30
50
60
0
0
80


Pigweed
0
0
0
0
0
0
0
70
70
50
0
0
90


Ragweed
0
0
0
0
0
0
0
80
70
0
0
0
0


Ryegrass, Italian
0
0
30
0
0
0
0
20
40
20
0
0
60











125 g ai/ha
Compounds





















Preemergence
397
398
399
400
401
402
403
404
405
406
407
408
409
410





Barnyardgrass
80
90
90
90
90
90
90
90
90
90
70
0
70
50


Foxtail, Giant
90
90
90
90
80
90
90
90
90
90
80
0
80
70



Kochia

70
70
80
60
50
40
70
60
50
0
0
0
0
0


Pigweed
90
70
70
60
20
30
30
30
50
20
0
0
0
0


Ragweed
50
20
50
70
0

50
0
20
0
0
0
0
0


Ryegrass, Italian
30
30
20
30
0
20
20
0
0
20
0
0
0
0











125 g ai/ha
Compounds





















Preemergence
411
412
413
414
415
416
417
418
419
420
421
422
423
424





Barnyardgrass
70
40
0
0
0
0
0
0
60
70
90
40
0
30


Foxtail, Giant
80
60
0
0
0
0
0
0
80
90
90
60
0
70



Kochia

0
0
0
0
0
0
0
0
0
0
70
0
0
0


Pigweed
0
0
0
0
0
0
0
0
0
0
20
20
0
0


Ragweed
0
0
0
0
0
0
0
0
0
0
30
0
0
0


Ryegrass, Italian
0
0
0
0
0
0
0
0
0
0
0
0
0
0











125 g ai/ha
Compounds





















Preemergence
425
426
427
428
429
430
431
432
433
434
435
436
437
438





Barnyardgrass
0
50
40
90
90
80
90
30
90
90
80
90
90
90


Foxtail, Giant
40
80
90
90
90
90
90
0
90
90
90
90
90
100



Kochia

0
0
30
50
70
30
30
0
70
70
60
70
60
70


Pigweed
0
0
0
0
80
0
70
0
20
80
60
80
20
80


Ragweed
0
0
0
0
50
30
40
0
70
50
20
0
0
60


Ryegrass, Italian
0
0
0
20
70
40
70
0
20
60
0
40
0
50











125 g ai/ha
Compounds





















Preemergence
439
440
441
442
443
444
445
446
447
448
449
450
451
452





Barnyardgrass
90
90
90
90
90
90
90
90
70
90
50
90
0
60


Foxtail, Giant
90
90
90
90
90
90
90
90
90
90
80
90
0
90



Kochia

70
60
70
80
30
60
50
50
50
20
20
50
0
60


Pigweed
50
20
50
70
80
80
30
40
30
20
0
70
0
80


Ragweed
0
20
30
20
80
50
20
50
0
0
0
20
0
20


Ryegrass, Italian
0
0
70
60
40
40
30
20
20
0
20
0
0
0











125 g ai/ha
Compounds



















Preemergence
453
454
455
456
457
460
461
462
463
464
465
466





Barnyardgrass
80
70
70
0
0
80
70
80
50
90
90
90


Foxtail, Giant
90
80
80
0
0
90
90
80
80
90
100
70



Kochia

0
0
20
0
0
0
0
30
0
70
80
0


Pigweed
20
0
0
0
0
30
0
0
0
70
50
0


Ragweed
0
0
0
0
0
0
0
10
0
50
40
0


Ryegrass, Italian
0
0
0
0
0
40
20
0
0
70
70
0











125 g ai/ha
Compounds





















Preemergence
467
468
469
470
471
472
473
474
475
476
477
478
479
480





Barnyardgrass
90
0
80
90
70
90
80
90
90
90
20
20
0
0


Foxtail, Giant
90
0
80
90
90
90
90
90
90
90
90
70
80
70



Kochia

30
40
0
70
0
80
80
60
70
50
0
0
0
0


Pigweed
0
0
0
0
0
80
80
30
60
30
0
0
0
0


Ragweed
30
0
0
0
0
0
20
0
50
0
0
0
0
0


Ryegrass, Italian
0
0
0
0
0
50
0
0
20
0
0
0
0
0











125 g ai/ha
Compounds





















Preemergence
481
482
483
484
485
486
487
488
489
490
491
492
493
494





Barnyardgrass
0
0
0
0
30
30
90
90
90
80
90
90
90
70


Foxtail, Giant
50
70
70
50
70
60
90
90
90
90
90
90
90
80



Kochia

0
0
0
0
0
0
30
70
20
0
0
60
0
0


Pigweed
0
0
0
0
0
0
0
50
0
0
0
0
0
0


Ragweed
0
0
0
0
0
0
30
70
30
0
0
30
0
0


Ryegrass, Italian
0
0
0
0
0
0
20
30
30
20
20
50
0
0











125 g ai/ha
Compounds





















Preemergence
495
496
497
498
499
500
501
502
503
504
505
506
507
508





Barnyardgrass
30
60
90
30
30
0
80
0
90
90
0
90
40
70


Foxtail, Giant
90
30
90
40
30
80
80
80
90
90
0
90
0
40



Kochia

20
0
20
0
0
50
0
0
0
80
0
0
0
0


Pigweed
0
0
30
0
0
0
0
0
0
80
0
30
0
0


Ragweed
0
0
0
0
0
0
0
0
0
40
0
0
0
0


Ryegrass, Italian
0
0
0
0
0
0
0
0
0
40
0
20
0
0











125 g ai/ha
Compounds





















Preemergence
509
510
513
514
515
516
517
518
519
520
521
522
523
524





Barnyardgrass
60
60
40
90
0
40
0
0
90
90
90
90
90
20


Foxtail, Giant
40
60
90
90
0
70
0
70
90
90
90
90
90
40



Kochia

0
30
0
0
0
0
0
0
40
50
0
60
0
0


Pigweed
0
0
0
0
0
0
0
0
0
30
60
70
80
0


Ragweed
0
30
0
0
0
0
0
0
0
0
40
0
60
0


Ryegrass, Italian
0
0
20
20
0
0
0
0
50
30
30
30
40
0











125 g ai/ha
Compounds



















Preemergence
525
526
527
534
535
536
537
538
539
540
541
544





Barnyardgrass
30
0
0
0
0
0
0
0
90
80
90
30


Foxtail, Giant
30
70
80
0
0
0
0
0
90
90
90
70



Kochia

0
0
0
0
0
0
0
0
60
0
0
0


Pigweed
0
0
0
0
0
0
0
0
40
0
0
0


Ragweed
0
0
0
0
0
0
0
0
0
0
0
0


Ryegrass, Italian
0
0
0
0
0
0
0
0
30
0
0
0











125 g ai/ha
Compounds




















Preemergence
545
546
547
549
550
551
552
553
554
557
558
559
560





Barnyardgrass
20
80
90
40
40
30
90
90
90
0
90
90
90


Foxtail, Giant
80
90
90
90
90
80
90
90
90
0
90
90
100



Kochia

0
0
0
0
0
0
0
60
70
0
70
60
60


Pigweed
0
0
0
0
0
0
0
30
0
0
30
20
0


Ragweed
0
0
0
0
0
0
0
40
20
0
50
0
0


Ryegrass, Italian
0
0
0
0
0
0
20
70
20
0
0
0
0











125 g ai/ha
Compounds





















Preemergence
561
562
563
564
565
566
567
568
569
570
571
572
573
574





Barnyardgrass
90
90
90
90
80
90
100
90
90
100
90
90
90
90


Foxtail, Giant
90
90
90
90
90
90
100
100
100
100
90
90
90
90



Kochia

70
70
70
80
70
70
60
70
60
60
60
70
70
40


Pigweed
80
90
70
90
70
80
20
30
50
40
30
40
40
20


Ragweed
80
70
50
80
50
60
50
20
60
0
0
0
0
0


Ryegrass, Italian
0
60
0
40
0
20
60
70
30
60
60
50
80
40











125 g ai/ha
Compounds





















Preemergence
575
576
577
587
588
589
590
591
592
593
594
595
596
597





Barnyardgrass
90
90
90
90
90
80
90
90
90
90
90
90
90
20


Foxtail, Giant
90
90
90
90
90
80
90
90
90
90
90
90
100
20



Kochia

0
20
50
0
0
0
0
30
0
0
0
40
20
0


Pigweed
0
20
0
0
0
0
0
0
0

0
30
0
0


Ragweed
0
20
0
0
0
0
0
0
0
0
0
0
0
0


Ryegrass, Italian
60
20
40
20
80
0
0
20
0
0
30
20
40
0











125 g ai/ha
Compounds



















Preemergence
598
599
600
601
602
605
606
607
608
609
610
611





Barnyardgrass
0
0
30
60
0
30
50
0
0
90
90
90


Foxtail, Giant
0
0
30
70
0
90
80
80
90
90
90
90



Kochia

0
0
0
0
0
0
0
0
50
60
60
40


Pigweed
0
0
0
0
0
0
0
0
70
60
80
70


Ragweed
0
0
0
0
0
0
0
0
50
60
0
0


Ryegrass, Italian
0
0
0
0
0
0
0
0
0
50
40
60











125 g ai/ha
Compounds




















Preemergence
612
613
614
616
617
618
619
620
621
622
623
624
625





Barnyardgrass
90
90
50
90
90
90
0
70
90
90
90
90
80


Foxtail, Giant
90
90
90
90
90
90
0
80
90
90
90
90
90



Kochia

20
60
0
70
70
90
20
0
0
80
60
40
50


Pigweed
70
70
0
80
90
50
0
0
0
80
80
80
50


Ragweed
50
60
0
80
30

0
0
0
60
80
60
20


Ryegrass, Italian
50
70
0
80
70
50
0
0
0
40
80
40
30











125 g ai/ha
Compounds

















Preemergence
630
631
632
633
634
635
636
637
638
639





Barnyardgrass
90
0
90
90
20
90
90
90
90
90


Foxtail, Giant
80
0
90
90
60
90
90
90
90
90



Kochia

0
0
50
30
0
60
50
40
0
70


Pigweed
0
0
0
0
0
60
40
80
40
50


Ragweed
0
0
60
0
0
40
20
40
30
50


Ryegrass, Italian
0
0
60
30
0
20
90
50
30
60











125 g ai/ha
Compounds





















Preemergence
640
641
642
643
644
645
646
647
648
649
650
651
652
653





Barnyardgrass
90
90
90
90
90
90
90
90
70
80
100
90
90
90


Foxtail, Giant
90
90
90
100
90
90
90
90
60
50
100
90
100
90



Kochia

50
20
40
0
50
0
60
0
0
60
30
60
0
0


Pigweed
80
20
50
0
60
0
60
0
0
50
50
40
0
70


Ragweed
40
0
0
0
50
0
60
0
0
20
0
50
0
50


Ryegrass, Italian
20
20
50
20
60
20
60
30
30
30
40
90
60
70











125 g ai/ha
Compounds





















Preemergence
654
655
656
657
658
659
660
661
662
663
664
665
666
667





Barnyardgrass
90
90
90
90
90
90
60
90
90
90
90
90
90
90


Foxtail, Giant
90
90
90
90
90
90
80
90
100
90
90
100
100
90



Kochia

0
30
60
20
0
0
0
50
70
70
70
60
20
40


Pigweed
40
50
30
20
0
0
0
0
70
30
60
30
0
20


Ragweed
0
0
20
20
50
0
0
70
80
30
20
20
0
60


Ryegrass, Italian
40
40
30
20
0
0
0
30
40
30
20
20
20
80














125 g ai/ha
Compounds



















Preemergence
668
674
675
676
677
678
679
680
681







Barnyardgrass
90
60
70
70
60
90
80
30
70



Foxtail, Giant
90
70
70
80
40
80
90
60
90




Kochia

20
0
0
0
20
0
30
0
20



Pigweed
20
0
0
0
0
0
0
0
0



Ragweed
0
0
0
0
0
0
0
0
0



Ryegrass, Italian
0
0
0
0
20
0
20
0
0












125 g ai/ha
Compounds





















Preemergence
682
683
684
685
686
687
688
689
690
691
692
693
694
695





Barnyardgrass
0
20
60
60
90
90
90
90
90
90
70
80
70
90


Foxtail, Giant
90
90
90
90
90
90
90
90
90
90
80
90
90
90



Kochia

0
0
0
0
0
0
30
20
80
80
70
80
0
30


Pigweed
0
0
0
0
0
0
30
20
80
70
80
70
0
30


Ragweed
0
0
0
0
0
0
20
0
70
60
50
50
0
20


Ryegrass, Italian
20
0
0
20
0
0
0
0
60
50
20
60
0
40











125 g ai/ha
Compounds


















Preemergence
696
697
698
699
700
701
702
703
704
705
706





Barnyardgrass
80
90
80
90
90
60
70
20
40
0
0


Foxtail, Giant
90
90
90
90
90
90
90
80
90
0
0



Kochia

40
30
50
0
30
0
20
0
0
0
0


Pigweed
20
50
50
30
40
0
0
0
0
0
0


Ragweed
0
50
0
0
0
0
0
0
0
0
0


Ryegrass, Italian
30
40
30
20
0
0
0
0
0
0
0













125 g ai/ha
Compounds














Preemergence
711
712
714
715
716







Barnyardgrass
0
0
0
0
0



Corn


0
0
0



Crabgrass, Large


20 
0
0



Foxtail, Giant
0
0
0
0
0




Kochia

0
0






Morningglory


0
0
0



Pigweed
0
0
0
0
0



Ragweed
0
0






Ryegrass, Italian
0
0






Velvetleaf


0
0
0



Wheat


0
0
0












125 g ai/ha
Compounds





















Preemergence
717
718
719
720
721
722
723
724
725
726
727
728
729
730





Barnyardgrass
90 
90 
90
90 
30 
20 
0
0
90 
90
70 
80
0
90


Corn
















Crabgrass, Large
















Foxtail, Giant
80 
70 
90
60 
30 
50 
0
0
90 
90
80 
30
0
90


Foxtail, Green

















Kochia

0
0
70
20 
0
0
0
0
0
70
0
30
0
70


Morningglory
















Pigweed
0
0
50
0
0
0
0
0
0
80
0
 0
0
30


Ragweed
0
0
20
0
0
0
0
0
0
30
0
 0
0
50


Ryegrass, Italian
0
30 
70
0
0
0
0
0
0
50
0
20
0
20


Velvetleaf
















Wheat

























125 g ai/ha
Compounds





















Preemergence
731
732
733
734
735
736
737
738
739
740
741
742
743
744





Barnyardgrass
80
90
90
90
90
90
70
90 
90
90
0
90
90
20


Corn
















Crabgrass, Large
















Foxtail, Giant
40
90
90
90
90
90
90
90 
90
100 
0
90
90
90


Foxtail, Green

















Kochia

 0
70
20
20
20
20
40
0
30
80
0
60
60
60


Morningglory
















Pigweed
 0
 0
20
20
 0
 0
 0
0
 0
70
0
20
 0
20


Ragweed
 0
 0
70
20
 0
 0
 0
0
50
40
0
20
 0
 0


Ryegrass, Italian
20
80
40
40
80
90
40
0
 0
60
0
50
90
 0


Velvetleaf
















Wheat

























125 g ai/ha
Compounds





















Preemergence
745
746
747
748
749
750
751
752
753
754
755
756
757
758





Barnyardgrass
90
0
 0
0
0
80 
90
30
70
80 
0
100 
90
100 


Corn
















Crabgrass, Large
















Foxtail, Giant
90
80 
90
40 
50 
50 
80
90
70
70 
0
100 
90
100 


Foxtail, Green

















Kochia

90
0
60
0
0
0
20
60
20
0
0
70
70
0


Morningglory
















Pigweed
80
0
50
0
0
0
 0
20
 0
0
0
40
30
0


Ragweed
80
0
20
0
0
0
20
40
 0
0
0
 0
20
0


Ryegrass, Italian
70
0
 0
0
0
0
 0
20
 0
0
0
30
30
30 


Velvetleaf
















Wheat

























125 g ai/ha
Compounds





















Preemergence
759
760
761
762
763
764
765
766
767
768
769
770
771
772





Barnyardgrass
90 
100 
90 
100 
80 
100 
100 
70 
90 
90 
70
90 
90
0


Corn
















Crabgrass, Large
















Foxtail, Giant
70 
100 
60 
70 
0
70 
30 
0
0
90 
90
90 
90
50 


Foxtail, Green

















Kochia

0
0
30 
0
30 
0
0
0
0
60 
30
0
50
0


Morningglory
















Pigweed
0
0
0
0
0
0
0
0
0
0
30
90 
 0
0


Ragweed
0
0
0
0
0
0
0
0
0
0
30
0
 0
0


Ryegrass, Italian
0
0
0
20 
0
0
0
0
0
0
 0
0
40
0


Velvetleaf
















Wheat

























125 g ai/ha
Compounds





















Preemergence
773
774
775
776
777
778
779
780
781
782
783
785
786
787





Barnyardgrass
0
0
60
90
70
70
90
80
80
80
0
90
80
20


Corn
















Crabgrass, Large
















Foxtail, Giant
0
0
80
90
80
90
90
90
90
90
0
90
90 
70


Foxtail, Green

















Kochia

0
0
30
50
 0
80
70
40
50
80
30 
20
0
80


Morningglory
















Pigweed
0
0
30
30
 0
30
40
 0
 0
 0
0
 0
0
50


Ragweed
0
0
50
30
 0
40
20
40
 0
 0
0
 0
0
70


Ryegrass, Italian
0
0
 0
20
40
 0
40
 0
20
40
0
 0
0
 0


Velvetleaf
















Wheat

























125 g ai/ha
Compounds





















Preemergence
788
789
790
791
792
793
794
795
796
797
798
799
800
801





Barnyardgrass
90
90 
90
90
0
0
90 
80 
90
90
80
40
90
90


Corn
















Crabgrass, Large
















Foxtail, Giant
90
60 
70
50
0
0
90 
70 
90
90
90
90
90
90


Foxtail, Green

















Kochia

80

70
50
0
0
0
0
20
20
20
40
 0
70


Morningglory
















Pigweed
80
0
 0
 0
0
0
0
0
40
20
40
40
20
30


Ragweed
80
0
20
 0
0
0
0
0
 0
 0
 0
 0
 0
60


Ryegrass, Italian
 0
0
30
 0
0
0
0
0
20
50
 0
 0
40
20


Velvetleaf
















Wheat

























125 g ai/ha
Compounds





















Preemergence
802
803
804
805
806
807
808
809
810
811
812
813
814
815





Barnyardgrass
90
90
90
0
0
100 
100 
90 
90 
40 
90 
80 
0
90


Corn
















Crabgrass, Large
















Foxtail, Giant
90
90
80
0
0
100 
90 
20 
90 
40 
90 
90 
0
90


Foxtail, Green

















Kochia

50
70
20
0
0
50
0
0
0
0
0
0
0
70


Morningglory
















Pigweed
50
60
60
0
0
40
0
0
0
0
0
0
0
30


Ragweed
60
60
 0
0
0
 0
0
0
0
0
0
0
0
 0


Ryegrass, Italian
40
 0
50
0
0
70
30 
0
20 
0
20 
20 
0
80


Velvetleaf
















Wheat

























125 g ai/ha
Compounds





















Preemergence
816
817
818
819
820
821
822
823
824
825
826
827
828
829





Barnyardgrass
90
90
90
90
90
90
90
90 
90
70
90
90
70
90


Corn
















Crabgrass, Large
















Foxtail, Giant
90
90
90
100 
90
90
90
100 
90
90
100 
90
90
90


Foxtail, Green

















Kochia

60
50
70
70
70
70
70
0
60
20
70
30
40
60


Morningglory
















Pigweed
 0
 0
20
30
40
50
 0
0
 0
 0
 0
20
 0
 0


Ragweed
20
20
 0
 0
20
 0
 0
0
20
20
20
 0
 0
30


Ryegrass, Italian
70
20
60
80
60
80
20
30 
20
20
70
30
50
20


Velvetleaf
















Wheat

























125 g ai/ha
Compounds





















Preemergence
830
831
832
833
834
835
836
837
838
839
840
841
842
843





Barnyardgrass
90
50
40
90
90
90
90
90
90
80
80
90
90
60


Corn
















Crabgrass, Large
















Foxtail, Giant
90
90
 0
90
90
90
90
90
90
90
90
90
90
90


Foxtail, Green

















Kochia

70
 0
90
70
80
80
90
90
70
90
 0
40
80
60


Morningglory
















Pigweed
20
20
 0
 0
 0
20
30
20
80
90
30
 0
40
 0


Ragweed
 0
 0
40
 0
 0
 0
 0
70
40
80
 0
 0
70
 0


Ryegrass, Italian
 0
30
 0
70
70
30
90
50
20
 0
 0
 0
30
 0


Velvetleaf
















Wheat

























125 g ai/ha
Compounds





















Preemergence
844
845
846
847
848
849
850
851
852
853
854
855
856
857





Barnyardgrass
0
90 
90
0
90
90
90
90
90
90
0
90
90
90


Corn
















Crabgrass, Large
















Foxtail, Giant
0
80 
90
0
90
90
90
90
90
90
50 
90
90
80


Foxtail, Green

















Kochia

0
40 
20
0
40
80
30
20
 0
40
0
20
40
 0


Morningglory
















Pigweed
0
0
 0
0
40
40
20
60
20
40
0
30
20
60


Ragweed
0
0
 0
0
 0
80
 0
 0
 0
 0
0
 0
 0
 0


Ryegrass, Italian
0
0
60
0
40
80
70
 0
 0
 0
0
 0
50
40


Velvetleaf
















Wheat

























125 g ai/ha
Compounds





















Preemergence
858
859
860
861
862
863
864
865
866
867
868
869
870
871





Barnyardgrass
90
90
90
90
90
50
90
0
30
90
30 
60 
50 
20 


Corn
















Crabgrass, Large
















Foxtail, Giant
90
90
90
90
90
90
90
0
90
90
20 
90 
20 
80 


Foxtail, Green

















Kochia

60
50
 0
30
70
80
60
0
20
50
0
0
0
80 


Morningglory
















Pigweed
20
60
60
50
80
70
90
0
 0
 0
0
0
0
0


Ragweed
 0
 0
 0
 0
90
 0
20
0
 0
 0
0
0
0
0


Ryegrass, Italian
30
20
20
30
 0
 0
 0
0
50
60
0
0
0
0


Velvetleaf
















Wheat

























125 g ai/ha
Compounds





















Preemergence
872
873
874
875
876
877
878
879
880
881
882
883
885
886





Barnyardgrass
90
90
90
90
60 
90 
100 
100 
90
80
90
90
70 
90 


Corn
















Crabgrass, Large
















Foxtail, Giant
90
90
90
90
80 
90 
100 
100 
100 
80
70
60
50 
90 


Foxtail, Green

















Kochia

 0
80
60
50
0
60 
70
80
70
30
70
30
0
80 


Morningglory
















Pigweed
 0
40
20
 0
0
0
 0
70
70
 0
20
 0
0
0


Ragweed
60
40
20
 0
0
0
30
50
50
 0
30
 0
0
0


Ryegrass, Italian
 0
50
40
 0
0
0
30
60
20
30
 0
 0
0
0


Velvetleaf
















Wheat

























125 g ai/ha
Compounds





















Preemergence
887
888
889
890
891
892
893
894
895
896
897
898
899
900





Barnyardgrass
90 
90 
90
90
60 
100 
90
90
90
90
80
90
90
90


Corn
















Crabgrass, Large
















Foxtail, Giant
80 
80 
90
90
80 
100 
90
90
90
90
90
90
90
90


Foxtail, Green

















Kochia

0
60 
80
40
0
70
80
60
90
30
60
70

90


Morningglory
















Pigweed
0
0
 0
30
0
 0
30
20
50
20
30
60
20
80


Ragweed
0
0
30
 0
0
20
40
 0
 0
 0
20
60
20
50


Ryegrass, Italian
0
0
30
50
0
30
40
50
90
40
20
40
30
60


Velvetleaf
















Wheat

























125 g ai/ha
Compounds





















Preemergence
901
902
903
904
905
906
907
908
909
910
911
912
913
914





Barnyardgrass
90
40 
90 
90 
70 
0
70 
0
70 
90
90
80
80 
70


Corn
















Crabgrass, Large
















Foxtail, Giant
90
30 
90 
90 
90 
0
80 
30 
90 
90
90
90
50 
90


Foxtail, Green

















Kochia

80
0
20 
90 
10 
0
0
0
0
60
90
60
0
60


Morningglory
















Pigweed
30
0
0
0
0
0
0
0
0
 0
20
 0
0
90


Ragweed
 0
0
0
0
0
0
0
0
0
 0
 0
 0
0
 0


Ryegrass, Italian
20
0
0
0
0
0
0
0
0
50
70
40
0
 0


Velvetleaf
















Wheat

























125 g ai/ha
Compounds





















Preemergence
915
916
917
918
919
920
921
922
923
924
925
926
927
928





Barnyardgrass
100 
30
20 
0
0
70 
90 
60 
0
90 
30 
30 
0
90


Corn
















Crabgrass, Large
















Foxtail, Giant
90
70
30 
20 
0
80 
90 
90 
0
90 
80 
80 
0
90


Foxtail, Green

















Kochia

80
40
0
0
0
0
0
0
0
0
0
0
0
80


Morningglory
















Pigweed
80
 0
0
0
0
0
0
0
0
0
0
0
0
 0


Ragweed
80
 0
0
0
0
0
0
0
0
0
0
0
0
 0


Ryegrass, Italian
40
 0
0
0
0
0
50 
20 
0
20 
30 
0
0
40


Velvetleaf
















Wheat

























125 g ai/ha
Compounds





















Preemergence
929
930
931
932
933
934
935
936
937
938
939
940
941
942





Barnyardgrass
90
90
90
90
90
70
70
70
90
90
90
30 
80 
70


Corn
















Crabgrass, Large
















Foxtail, Giant
90
90
90
90
90
90
90
90
90
90
90
40 
90 
90


Foxtail, Green

















Kochia

70
70
90
40
50
50
70
60
80
70
30
0
0
70


Morningglory
















Pigweed
20
20
30
 0
30
 0
20
20
50
80
 0
0
0
80


Ragweed
 0
 0
 0
 0

 0
30
60
40
20
 0
0
0
40


Ryegrass, Italian
40
40
40
30
50
 0
20
40
20
20
 0
0
0
40


Velvetleaf
















Wheat

























125 g ai/ha
Compounds





















Preemergence
943
944
945
946
947
948
949
950
951
952
953
954
955
956





Barnyardgrass
90
90
60 
60 
30 
70 
70 
100 
90 
50 
90 
70 
100 
100 


Corn
















Crabgrass, Large
















Foxtail, Giant
90
90
0
0
50 
70 
60 
60
70 
80 
90 
90 
100 
100 


Foxtail, Green

















Kochia

70
 0
0
0
0
0
20 
50
0
30 
60 
0
30
90


Morningglory
















Pigweed
40
 0
0
0
0
0
0
 0
0
0
0
0
 0
 0


Ragweed
 0
50
0
0
0
0
0
 0
0
0
0
0
 0
20


Ryegrass, Italian
 0
 0
0
0
0
0
0
20
0
0
0
0
70
40


Velvetleaf
















Wheat

























125 g ai/ha
Compounds





















Preemergence
957
958
959
960
961
962
963
964
965
966
967
968
969
970





Barnyardgrass
70
90
90
80
90
90
90
90 
90 
80
80 
20 
50 
0


Corn
















Crabgrass, Large
















Foxtail, Giant
20
90
90
70
70
90
100 
90 
90 
80
80 
30 
90 
80 


Foxtail, Green

















Kochia

30
 0
70
20
70
50
40
0
0
30
0
0
0
0


Morningglory
















Pigweed
20
 0
 0
 0
 0
 0
 0
0
0
 0
0
0
0
0


Ragweed
 0
20
70
 0
60
20
 0
0
0
 0
0
0
0
0


Ryegrass, Italian
 0
 0
20
 0
30
 0
20
0
70 
20
0
0
40 
0


Velvetleaf
















Wheat

























125 g ai/ha
Compounds





















Preemergence
971
972
973
974
975
976
977
978
979
980
981
982
983
984





Barnyardgrass
90
80
90 
90
90
90
90
90
90
90
90 
90
90
100 


Corn
















Crabgrass, Large
















Foxtail, Giant
90
80
90 
90
90
90
90
90
90
90
90 
90
100 
100 


Foxtail, Green

















Kochia

 0
 0
0
90
50
70
90
40
50
 0
0
50
90
90


Morningglory
















Pigweed
20
 0
0
20
20
 0
40
 0
40
 0
0
 0
 0
40


Ragweed
20
20
0
90


70
90
50
 0
0

70
 0


Ryegrass, Italian
80
90
0
70
30
50
 0
60
50
20
0
90
30
70


Velvetleaf
















Wheat

























125 g ai/ha
Compounds





















Preemergence
985
986
987
988
989
990
991
992
993
994
995
996
997
998





Barnyardgrass
0
90
60 
90
70 
100 
70 
0
90
90
80
0
0
0


Corn
















Crabgrass, Large
















Foxtail, Giant
0
100 
90 
90
70 
100 
90 
0
90
100 
90
0
0
0


Foxtail, Green

















Kochia

0
30
0
30
0
70
0
0
 0
40

0
0
0


Morningglory
















Pigweed
0
60
0
30
0
40
60 
0
40
30
20
0
0
0


Ragweed
0
50
0
50
0
50
0
0
 0
 0
 0
0
0
0


Ryegrass, Italian
0
60
0
 0
0
 0
0
0
80
70
20
0
0
0


Velvetleaf
















Wheat

























125 g ai/ha
Compounds





















Preemergence
999
1000
1001
1002
1003
1004
1005
1006
1007
1008
1009
1010
1011
1012





Barnyardgrass
70 
0
0
20 
0
0
0
0
0
0
0
0
0
0


Corn
















Crabgrass, Large
















Foxtail, Giant
90 
70 
0
30 
60 
30 
0
0
0
0
0
0
0
0


Foxtail, Green

















Kochia

0
0
0
0
0
0
0
0
0
0
0
0
0
0


Morningglory
















Pigweed
0
20 
0
20 
0
0
0
0
0
0
0
0
0
0


Ragweed
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Ryegrass, Italian
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Velvetleaf
















Wheat

























125 g ai/ha
Compounds





















Preemergence
1013
1014
1015
1016
1017
1018
1019
1020
1021
1022
1023
1024
1025
1026





Barnyardgrass
90
90
90
90 
90
90
0
90
100 
60
90
70
70 
90


Corn
















Crabgrass, Large
















Foxtail, Giant
90
90
90
90 
90
90
0
90
100 
100 
90
90
90 
30


Foxtail, Green

















Kochia

50
20
 0
0
 0
 0
0
30
70
70
 0
30
0
30


Morningglory
















Pigweed
30
30
 0
0
50
30
0
30
70
30
30
30
0
 0


Ragweed
 0
 0
 0
0
 0
 0
0
 0
70
 0
 0
 0
0
50


Ryegrass, Italian
30
 0
40
0
 0
 0
0
 0
 0
 0
50
 0
0
 0


Velvetleaf
















Wheat

























125 g ai/ha
Compounds





















Preemergence
1027
1028
1029
1030
1031
1032
1033
1034
1035
1036
1037
1038
1039
1040





Barnyardgrass
90
90
90
70
0
20 
90 
90
90
90
80
100 
90
90


Corn
















Crabgrass, Large
















Foxtail, Giant
40
90
90
90
0
0
70 
80
90
70
20
100 
90
90


Foxtail, Green

















Kochia

80
 0
 0
 0
0
0
0
60
 0
70
40
80
80
50


Morningglory
















Pigweed
 0
 0
 0
 0
0
0
0
 0
 0
 0
 0
20
20
30


Ragweed
70
 0
 0
 0
0
0
0
30
20
 0
 0
20
10



Ryegrass, Italian
30
30
70
70
0
0
0
20

20
50
30
60
50


Velvetleaf
















Wheat

























125 g ai/ha
Compounds





















Preemergence
1041
1042
1043
1044
1045
1046
1047
1048
1049
1050
1051
1052
1053
1054





Barnyardgrass
30
90
80
90 
90 
90
30
90
30
0
20
90
0
0


Corn
















Crabgrass, Large
















Foxtail, Giant
80
90
70
70 
80 
80
60
90
80
0
90
90
0
0


Foxtail, Green

















Kochia

30
20
60
0
0
60
60
90
30
0
 0
70
0
0


Morningglory
















Pigweed
 0
30
 0
0
0
 0
 0
80
 0
0
40
80
0
0


Ragweed
20
20
 0
0
0
40
40
50
20
0
 0
20
0
0


Ryegrass, Italian
 0
30
20
0
30 
60
 0
20
 0
0
 0
30
0
0


Velvetleaf
















Wheat

























125 g ai/ha
Compounds





















Preemergence
1055
1056
1057
1058
1059
1060
1061
1062
1063
1065
1066
1067
1068
1069





Barnyardgrass
0
90 
0
90 
70 
100 
80 
100 
100 
70
100 
100 
0
0


Corn
















Crabgrass, Large
















Foxtail, Giant
0
60 
0
90 
70 
100 
70 


100 
100 
100 
0
50 


Foxtail, Green







100 
100 








Kochia

0
0
0
0
0
 0
0
20
20
70
20
70
0
0


Morningglory
















Pigweed
0
0
0
0
0
30
0
 0
 0
70
20
 0
0
0


Ragweed
0
0
0
0
0
30
0
 0
30
 0
 0
60
0
0


Ryegrass, Italian
0
0
0
0
0
60
0
20
 0
30
50
70
0
0


Velvetleaf
















Wheat

























125 g ai/ha
Compounds





















Preemergence
1070
1071
1072
1073
1074
1075
1076
1077
1078
1079
1080
1081
1082
1083





Barnyardgrass
0
90 
100 
100
100 
100 
90 
100 
0
80 
0
90 
0
100 


Corn
















Crabgrass, Large
















Foxtail, Giant
60 
100 
100 
100
100 
100 
100 
100 
0
100 
0
100 
0
100 


Foxtail, Green

















Kochia

0
0
0
 0
20
30
0
20
0
0
10 
30 
0
90


Morningglory
















Pigweed
0
0
0
100
20
20
20 
 0
0
0
0
0
0
20


Ragweed
0
0
0
 10
10
20
0
 0
0
0
0
0
0
80


Ryegrass, Italian
0
0
0
 0
50
80
0
10
0
0
0
0
0
60


Velvetleaf
















Wheat

























125 g ai/ha
Compounds





















Preemergence
1084
1085
1086
1087
1088
1089
1090
1091
1092
1093
1094
1095
1096
1097





Barnyardgrass
70
90 
80 
90
30 
90
90 
0
90
90
0
0
0
0


Corn
















Crabgrass, Large
















Foxtail, Giant
100 
100 
100 
100 
100 
100 
100 
100 
100 
100 
90 
0
0
0


Foxtail, Green

















Kochia

20
0
0
60
20 
20
30 
40 
0
50
0
0
0
0


Morningglory
















Pigweed
 0
0
0
 0
0
 0
0
0
0
80
0
0
0
0


Ragweed
10
0
0
 0
0
60
0
0
40 
20
0
0
0
0


Ryegrass, Italian
10
0
30 
30
0
10
0
0
0
 0
0
0
0
0


Velvetleaf
















Wheat

























125 g ai/ha
Compounds





















Preemergence
1098
1099
1100
1101
1102
1103
1104
1105
1106
1107
1108
1109
1110
1111





Barnyardgrass
90
90
90 
90
90
70
50 
60
90
0
0
100 
100 
0


Corn
















Crabgrass, Large
















Foxtail, Giant
90
90
90 
90
90
90
70 
90
90
0
0
100 
100 
0


Foxtail, Green

















Kochia

20
60
50 
60
20

0
70
60
0
0
70
70
0


Morningglory
















Pigweed
 0
 0
0
 0
20
 0
0
 0
20
0
0
90
90
0


Ragweed
 0
20
0
 0
 0
20
0
20
30
0
0
50
40
0


Ryegrass, Italian
20
50
0
30
30
 0
0
 0
 0
0
0
80
50
0


Velvetleaf
















Wheat

























125 g ai/ha
Compounds





















Preemergence
1112
1113
1114
1115
1116
1117
1118
1119
1120
1121
1122
1123
1124
1125





Barnyardgrass
0
0
90 
90
90 
90
80
90
90
90
90
90
60
90


Corn
















Crabgrass, Large
















Foxtail, Giant
0
0
90 
90
20 
50
60
50
90
90
90
90
90
90


Foxtail, Green

















Kochia

0
0

70
0
40
 0
70
40
80
60
60
70
50


Morningglory
















Pigweed
0
0
0
 0
0
 0
 0
 0
 0
 0
30
 0
50
 0


Ragweed
0
0
0
 0
0
20
20
70
40
50
70
20
 0
 0


Ryegrass, Italian
0
0
0
50
0
 0
40
20
20
50
70
40
 0
 0


Velvetleaf
















Wheat

























125 g ai/ha
Compounds





















Preemergence
1126
1127
1129
1130
1131
1132
1133
1134
1135
1136
1137
1138
1139
1140





Barnyardgrass
90
0
80 
0
90
90 
90
30 
0
30 
0
90 
90
90


Corn
















Crabgrass, Large
















Foxtail, Giant
90
0
90 
0
90
100 
90
70 
0
30 
0
90 
90
100 


Foxtail, Green

















Kochia

70
0
0
0
100 
0
60
50 
0
0
0
0
30
80


Morningglory
















Pigweed
30
0
0
0
80
0
30
0
0
0
0
0
 0
 0


Ragweed
60
0
0
0
60
0
40
0
0
0
0
0
50
30


Ryegrass, Italian
 0
0
20 
0
 0
30 
20
0
0
0
0
30 
30
30


Velvetleaf
















Wheat

























125 g ai/ha
Compounds





















Preemergence
1141
1142
1143
1144
1145
1146
1147
1148
1149
1150
1151
1152
1153
1154





Barnyardgrass
80
30
40 
90
90
70
20 
90
90
70 
90
20
80
90


Corn
















Crabgrass, Large
















Foxtail, Giant
90
90
80 
90
90
80
20 
90
90
90 
100 
70
90
90


Foxtail, Green

















Kochia

 0
 0
0
60
50
 0
0
 0
20
0
70
 0
60
70


Morningglory
















Pigweed
60
60
0
80
 0
 0
0
 0
40
0
80
60
 0
60


Ragweed
 0
 0
0
20
 0
 0
0
 0
 0
0
 0
 0
 0
20


Ryegrass, Italian
40
 0
0
50
30
30
0
20
20
0
70
 0
30
30


Velvetleaf
















Wheat

























125 g ai/ha
Compounds





















Preemergence
1155
1156
1157
1158
1159
1160
1161
1162
1163
1164
1165
1166
1167
1168





Barnyardgrass
90
90
90
90
60 
90 
0
90 
90
80
90
20 
0
0


Corn
















Crabgrass, Large
















Foxtail, Giant
70
90
90
100 
70 
90 
20 
90 
60
30
90
80 
50 
30 


Foxtail, Green

















Kochia

60
70
90
30
0
0
0
0
20
20
70
0
0
0


Morningglory
















Pigweed
 0
 0
30
 0
0
0
0
0
 0
 0
50
0
0
0


Ragweed
40
100 
 0
 0
0
0
0
0
 0
 0
30
0
0
0


Ryegrass, Italian
 0
20
30
60
0
0
0
20 
 0
 0
 0
0
0
0


Velvetleaf
















Wheat

























125 g ai/ha
Compounds





















Preemergence
1169
1170
1171
1172
1173
1174
1175
1176
1177
1178
1179
1180
1181
1182





Barnyardgrass
90 
40 
80
0
90
100 
90
90
70
20
0
20 
0
0


Corn
















Crabgrass, Large
















Foxtail, Giant
90 
70 
90
0
80
90 
90
90
70
20
0
0
0
0


Foxtail, Green

















Kochia

30 
0
30
0
20
0
50
40
30
40
0
0
0
0


Morningglory
















Pigweed
0
0
40
0
 0
0
40
40
 0
20
0
0
0
0


Ragweed
0
0
 0
0
40
0
20
 0
 0
 0
0
0
0
0


Ryegrass, Italian
0
0
60
0
30
40 
20
50
30
 0
0
0
0
0


Velvetleaf
















Wheat

























125 g ai/ha
Compounds





















Preemergence
1183
1184
1185
1186
1187
1188
1189
1190
1191
1192
1193
1194
1195
1196





Barnyardgrass
90 
100 
100 
100 
100 
100 
100 
90 
0
100 
90 
0
0
50 


Corn
















Crabgrass, Large
















Foxtail, Giant
90 
90 
90 
100 
100 
100 
100 
90 
0
100 
80 
0
0
70 


Foxtail, Green

















Kochia

0
0
0
80
70
80
70
0
0
50
0
0
0
0


Morningglory
















Pigweed
0
0
0
70
20
80
40
0
0
30
0
0
0
0


Ragweed
0
0
0
60
50
70
50
0
0
 0
0
0
0
0


Ryegrass, Italian
50 
50 
60 
70
40
60
60
0
0
 0
0
0
0
0


Velvetleaf
















Wheat

























125 g ai/ha
Compounds





















Preemergence
1197
1198
1199
1200
1201
1202
1203
1204
1205
1206
1207
1208
1209
1210





Barnyardgrass
100
70
90 
0
 0
90 
80
90
90
70
60
90
90
90 


Corn
















Crabgrass, Large
















Foxtail, Giant
100
100 
90 
0
70
50 
80
90
100 
80
80
100 
90
100 


Foxtail, Green

















Kochia

100
80
0
0
30
20 
20
80
30
60
30
70
60
0


Morningglory
















Pigweed
 80
70
0
0
20
0
 0
70
 0
50
 0
60
 0
0


Ragweed
100
70
30 
0
60
0
30
90
 0
 0
30
40
60
0


Ryegrass, Italian
 70
30
0
0
 0
0
 0
70
40
 0
 0
20
 0
20 


Velvetleaf
















Wheat

























125 g ai/ha
Compounds





















Preemergence
1211
1212
1213
1214
1215
1216
1217
1218
1219
1220
1221
1222
1223
1224





Barnyardgrass
100 
80
100 
90
90 
0
90 
30 
70 
90
90
0
90 
40


Corn
















Crabgrass, Large
















Foxtail, Giant
100 
90
100 
90
60 
30 
90 
80 
80 
90
90
0
90 
80


Foxtail, Green

















Kochia

20
100 
70
50
0
0
0
0
0
40
40
0
0
 0


Morningglory
















Pigweed
50
80
50
60
0
0
0
0
0
20
 0
0
0
50


Ragweed
50
40
50
 0
0
0
0
0
0
30
20
0
0
 0


Ryegrass, Italian
50
 0
20
60
0
0
0
0
0
30
20
0
0
 0


Velvetleaf
















Wheat

























125 g ai/ha
Compounds





















Preemergence
1225
1226
1227
1228
1229
1230
1231
1232
1233
1234
1235
1236
1237
1238





Barnyardgrass
90
90
 0
90
90
 0
90
90
90
100 
100 
90
70 
80 


Corn
















Crabgrass, Large
















Foxtail, Giant
90
100 
50
90
100 
40
90
90
90
100 
100 
90
60 
90 


Foxtail, Green

















Kochia

60
60
 0
 0
90
70
70
70
70
70
60
20
0
60 


Morningglory
















Pigweed
30
80
30
20
60
20
40
70
40
70
30
60
0
0


Ragweed
50
 0
 0
 0
60
 0
30
60
30
40
70
 0
0
0


Ryegrass, Italian
20
80
20
30
 0
 0
40
20
40
40
50
30
0
0


Velvetleaf
















Wheat

























125 g ai/ha
Compounds





















Preemergence
1239
1240
1241
1242
1243
1244
1245
1246
1247
1248
1249
1250
1251
1252





Barnyardgrass
80
0
0
20 
0
80 
50 
60
70 
70 
100 
100 
100 
100 


Corn
















Crabgrass, Large
















Foxtail, Giant
90
0
0
30 
0
90 
80 
50
20 
0
100 
100 
100 
90


Foxtail, Green

















Kochia

90
0
0
0
0
0
0
60
0
0

 0
80
80


Morningglory
















Pigweed
20
0
0
0
0
0
0
 0
0
0
80
30
90
70


Ragweed
 0
0
0
0
0
0

40
0
0
30
 0
70
60


Ryegrass, Italian
50
0
0
0
0
0
0
 0
0
0
30
50
50
80


Velvetleaf
















Wheat

























125 g ai/ha
Compounds





















Preemergence
1253
1254
1255
1256
1257
1258
1259
1260
1261
1262
1263
1264
1265
1266





Barnyardgrass
90
100 
100 
100 
0
30 
60
90
90
90
0
0
90
90


Corn
















Crabgrass, Large
















Foxtail, Giant
100 
90
100 
90
0
70 
90
90
90
90
0
0
90
90


Foxtail, Green

















Kochia

80
20
60
30
0
0
 0
80
80
60
0
0
70
80


Morningglory
















Pigweed
50
20
60
30
0
0
30
90
20
50
0
0
80
80


Ragweed
40
 0
20
 0
0
0
 0
80
50
 0
0
0
 0
60


Ryegrass, Italian
20
 0
20
20
0
0
30
50
30
 0
0
0
60
40


Velvetleaf
















Wheat

























125 g ai/ha
Compounds





















Preemergence
1267
1268
1269
1270
1271
1272
1273
1274
1275
1276
1277
1278
1279
1280





Barnyardgrass
90 
90 
90
90
90
90
80
90
100 
100 
100 
100 
70 
0


Corn
















Crabgrass, Large
















Foxtail, Giant
90 
90 
90
90
90
90
90
90
100 
100 
100 
100 
20 
0


Foxtail, Green

















Kochia

0
0
50
60
40
20
50
70
20
60
0
30
0
0


Morningglory
















Pigweed
0
0
 0
40
50
 0
20
70
 0
30
0
90
0
0


Ragweed
0
0
 0
30
20
 0
 0
80
20
80
0
100 
0
0


Ryegrass, Italian
0
20 
30
40
90
60
40
20
 0
30
0
30
0
0


Velvetleaf
















Wheat

























125 g ai/ha
Compounds





















Preemergence
1281
1282
1283
1284
1285
1286
1287
1288
1289
1290
1291
1292
1293
1294





Barnyardgrass
40 
100 
0
0
90
100 
100 
0
30 
0
100
50
20 
50 


Corn
















Crabgrass, Large
















Foxtail, Giant
40 
100 
0
0
100 
100 
100 
0
50 
0
100
80
20 
30 


Foxtail, Green

















Kochia

0
70
0
0
30 
60
70
0
0
0
 40
60
0
0


Morningglory
















Pigweed
30 
80
0
0
0
20
40
0
0
0
100
40
0
0


Ragweed
0
90
0
0
30 
50
 0
0
0
0
 0
 0
0
0


Ryegrass, Italian
0
70
0
0
0
60
40
0
0
0
 20
40
0
0


Velvetleaf
















Wheat

























125 g ai/ha
Compounds





















Preemergence
1295
1296
1297
1298
1299
1300
1301
1302
1303
1304
1305
1306
1307
1308





Barnyardgrass
0
70 
20 
80 
90
90 
30 
60 
0
0
70 
60 
80
90 


Corn
















Crabgrass, Large
















Foxtail, Giant
40 
60 
80 
90 
90
90 
90 
90 
40 
0
90 
30 
50
90 


Foxtail, Green

















Kochia

0
0
0
0
70
0
30 
0
0
0
0
0
20
0


Morningglory
















Pigweed
0
0
0
0
20
0
0
0
0
0
0
0
 0
0


Ragweed
0
0
0
0
30
0
0
0
0
0
0
40 

0


Ryegrass, Italian
0
0
0
0
30
0
0
0
0
0
0
0
 0
0


Velvetleaf
















Wheat

























125 g ai/ha
Compounds





















Preemergence
1309
1310
1311
1312
1313
1314
1316
1317
1318
1319
1320
1321
1323
1324





Barnyardgrass
90
90 
100 
90
90 
100 
90
90
90
90
0
90
90
90


Corn
















Crabgrass, Large
















Foxtail, Giant
80
90 
100 
90
20 
90
90
90
90
90
0
90
90
90


Foxtail, Green

















Kochia

60
70 
70
50
90 
80
80
60
70
80
0
50
80
90


Morningglory
















Pigweed
 0
0
 0
20
0
 0
70
 0
70
 0
0
 0
 0
 0


Ragweed
40
0

70
0
80
 0
 0
 0
 0
0
50
 0
90


Ryegrass, Italian
 0
0
70
60
0
20
70
20
40
30
0
 0
20
20


Velvetleaf
















Wheat

























125 g ai/ha
Compounds





















Preemergence
1325
1326
1327
1328
1329
1330
1331
1332
1333
1334
1335
1336
1337
1338





Barnyardgrass
90
80
90
70 
90 
90
90 
70 
70 
20 
0
0
80 
100 


Corn
















Crabgrass, Large
















Foxtail, Giant
90
60
70
50 
90 
90
90 
80 
90 
40 
0
0
80 
90 


Foxtail, Green

















Kochia

80
30
100 
30 
50 
20
0
0
30 
0
0
0
0
0


Morningglory
















Pigweed
60
 0
 0
0
0
 0
0
0
0
20 
0
0
0
0


Ragweed
10
 0
 0
0
0
 0
0
0
0
0
0
0
0
0


Ryegrass, Italian
 0
20
20
0
0
50
20 
0
0
0
0
0
70 
0


Velvetleaf
















Wheat

























125 g ai/ha
Compounds





















Preemergence
1339
1340
1341
1342
1343
1344
1345
1346
1347
1348
1349
1350
1351
1352





Barnyardgrass
90
90
60 
90 
90
0
100 
90
100 
100 
100 
90
0
90


Corn
















Crabgrass, Large
















Foxtail, Giant
90
90
70 
100 
100 
0
100 
100 
100 
100 
100 
100 
0
100 


Foxtail, Green

















Kochia

50
 0
0
0
40
0
40
80
90
80
20 
70
0
60


Morningglory
















Pigweed
 0
20
0
20 
30
0
 0
90
100 
100 
0
90
0
80


Ragweed
 0
 0
0
0
 0
0
60
90
90
20
0
80
0
30


Ryegrass, Italian
20
 0
0
0
30
0
 0
30
30
60
0
30
0
40


Velvetleaf
















Wheat

























125 g ai/ha
Compounds





















Preemergence
1353
1354
1355
1356
1357
1358
1359
1360
1361
1362
1366
1367
1368
1369





Barnyardgrass
70
80
0
0
0
0
0
0
0
0
70
80 
100 
100 


Corn


0
0
0
0
0
0
0
0






Crabgrass, Large


0
0
0
20 
0
0
0
0






Foxtail, Giant
100 
100 
0
0
0
0
0
0
0
0
90





Foxtail, Green











60 
100 
100 



Kochia

80
20








 0
0
0
0


Morningglory


0
0
0
0
0
0
0
0






Pigweed
30
20
0
0
0
0
0
0
0
0
 0
0
0
0


Ragweed
 0
 0








 0
0
0
70 


Ryegrass, Italian
20
20








10
0
0
0


Velvetleaf


0
0
0
0
0
0
0
0






Wheat


0
0
0
0
0
0
0
0















125 g ai/ha
Compounds





















Preemergence
1370
1371
1372
1373
1374
1375
1376
1377
1378
1379
1380
1381
1382
1383





Barnyardgrass
90
90
90
90
0
100 
90 
80
90
100 
90
90
0
100 


Corn
















Crabgrass, Large
















Foxtail, Giant
90
90
90
100 
0
100 
90 
100 
90
100 
100 
100 
0
100 


Foxtail, Green

















Kochia


80
90
100 
0
70
0
70
80
90
80
80
0
90


Morningglory
















Pigweed
 0
70
90
90
0
 0
0
20
70
80
80
90
20 
80


Ragweed
40
70
90
100 
0
70
0
 0
50
70
70
70
0
80


Ryegrass, Italian
80
 0
60
60
0
70
20 
20
80
20
50
30
0
70


Velvetleaf
















Wheat

























125 g ai/ha
Compounds





















Preemergence
1384
1385
1386
1387
1388
1389
1390
1391
1392
1393
1394
1395
1396
1397





Barnyardgrass
90
90 
90
50 
100 
100 
90
90
0
90
90
90
90
100 


Corn
















Crabgrass, Large
















Foxtail, Giant
90
90 
90
80 
100 
100 
90
100 
0
90
90
90
90
100 


Foxtail, Green

















Kochia

30
0
80
30 
80
70
80
90
0
70
40
 0
70
60


Morningglory
















Pigweed
30
0
80
0
30
70
80
90
0
80
 0
 0
90
 0


Ragweed
 0
0
60
0
 0
 0
70
90
0
90
20
 0
60
 0


Ryegrass, Italian
30
0
50
0
90
80
30
30
0
20
50
50
40
70


Velvetleaf
















Wheat




























125 g ai/ha
Compounds














Preemergence
1398
1399
1400
1402







Barnyardgrass
100 
90
90
90



Corn







Crabgrass, Large







Foxtail, Giant
100 
90
90
100 



Foxtail, Green








Kochia

90
70
70
80



Morningglory







Pigweed
50
30
80
90



Ragweed
90
60
70
 0



Ryegrass, Italian
70
40
30
 0



Velvetleaf







Wheat
















31 g ai/ha
Compounds





















Preemergence
770
792
793
794
795
796
797
798
799
800
801
802
803
804





Barnyardgrass
70
0
0
70
30 
70
80
20
0
80
80
80
70
70


Foxtail, Giant
90
0
0
30
0
90
90
70
70
80
80
90
90
70


Foxtail, Green

















Kochia

0
0
0
0
0
0
0
0
0
0
40
0
50
0


Pigweed
40
0
0
0
0
20
0
30
30
0
30
40
40
0


Ragweed
0
0
0
0
0
0
0
0
0
0
20
0
30
0


Ryegrass, Italian
0
0
0
0
0
0
0
0
0
0
 0
0
 0
40











31 g ai/ha
Compounds





















Preemergence
805
806
807
808
809
810
811
812
813
814
970
971
972
997





Barnyardgrass
0
0
100
100
90 
90
0
70
20
0
0
70
70
0


Foxtail, Giant
0
0
100
70
0
70
0
80
70
0
20 
70
80
0


Foxtail, Green

















Kochia

0
0
0
0
0
0
0
0
0
0
0
0
0
0


Pigweed
0
0
0
0
0
0
0
0
0
0
0
20
0
0


Ragweed
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Ryegrass, Italian
0
0
20
0
0
0
0
0
0
0
0
50
50
0











31 g ai/ha
Compounds





















Preemergence
1003
1004
1005
1006
1007
1008
1009
1010
1011
1012
1050
1051
1052
1060





Barnyardgrass
0
0
0
0
0
0
0
0
0
0
0
0
30
90


Foxtail, Giant
0
0
0
0
0
0
0
0
0
0
0
30 
80
90


Foxtail, Green

















Kochia

0
0
0
0
0
0
0
0
0
0
0
0
20
0


Pigweed
0
0
0
0
0
0
0
0
0
0
0
0
40
0


Ragweed
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Ryegrass, Italian
0
0
0
0
0
0
0
0
0
0
0
0
0
50











31 g ai/ha
Compounds





















Preemergence
1061
1062
1063
1065
1066
1067
1068
1069
1070
1071
1072
1074
1075
1076





Barnyardgrass
40
100
100
0
50
30
0
0
0
40
90
90
100
0


Foxtail, Giant
20


90
100
90
0
0
0
90
90
100
100
80


Foxtail, Green

100
100














Kochia

0
0
10
0
0
0
0
0
0
0
0
0
0
0


Pigweed
0
0
0
30
0
0
0
0
0
0
0
0
0
0


Ragweed
0
70
0
0
0
0
0
0
0
0
0
0
30
10


Ryegrass, Italian
0
10
0
0
20
20
0
0
0
0
0
0
50
0











31 g ai/ha
Compounds





















Preemergence
1077
1078
1079
1080
1081
1082
1083
1084
1085
1086
1087
1088
1089
1090





Barnyardgrass
80
0
0
0
10
0
90
0
0
80
0
0
90
10


Foxtail, Giant
100
0
20 
0
100
0
100
30 
90 
90
90 
0
100
60


Foxtail, Green

















Kochia

0
0
0
0
20
0
20
0
0
0
0
30 
0
20


Pigweed
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Ragweed
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Ryegrass, Italian
0
0
0
0
0
0
20
0
0
0
0
0
0
30











31 g ai/ha
Compounds





















Preemergence
1091
1092
1093
1103
1104
1105
1106
1107
1108
1109
1110
1141
1142
1143





Barnyardgrass
0
40
40
20
0
30
50
0
0
100
90
30
0
0


Foxtail, Giant
50
90
100
70
0
20
60
0
0
100
90
80
30 
20 


Foxtail, Green

















Kochia

20
70
0
0
0
0
0
0
0
0
0
0
0
0


Pigweed
10
0
0
0
0
0
0
0
0
70
60
30
0
0


Ragweed
100
0
0
0
0
0
0
0
0
0
0
0
0
0


Ryegrass, Italian
0
0
0
0
0
0
0
0
0
60
30
0
0
0











31 g ai/ha
Compounds





















Preemergence
1144
1145
1146
1147
1148
1149
1150
1161
1162
1163
1164
1165
1166
1167





Barnyardgrass
90
80
50
0
30
70
0
0
40
70
60
70
0
0


Foxtail, Giant
90
90
20
0
90
80
30 
0
50
10
30
70
20 
0


Foxtail, Green

















Kochia

50
0
0
0
0
0
0
0
0
0
0
0
0
0


Pigweed
30
0
0
0
0
0
0
0
0
0
0
40
0
0


Ragweed
 0
0
0
0
0
0
0
0
0
0
0
0
0
0


Ryegrass, Italian
50
0
0
0
0
0
0
0
0
0
0
0
0
0











31 g ai/ha
Compounds





















Preemergence
1168
1169
1170
1171
1172
1173
1174
1175
1176
1183
1184
1185
1186
1187





Barnyardgrass
0
70
0
40
0
60
80
50
90
90
90
70
90
70


Foxtail, Giant
0
70
0
70
0
30
80
70
90
80
80
50
100
90


Foxtail, Green

















Kochia

0
30
0
0
0
0
0
20
0
0
0
0
70
50


Pigweed
0
0
0
0
0
0
0
0
0
0
0
0
30
0


Ragweed
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Ryegrass, Italian
0
0
0
0
0
0
0
0
40
20
40
0
20
0











31 g ai/ha
Compounds





















Preemergence
1188
1189
1190
1191
1192
1193
1237
1258
1259
1261
1262
1263
1264
1265





Barnyardgrass
90
90
50
0
70
40 
0
0
0
90
70
0
0
80


Foxtail, Giant
90
90
60
0
30
0
20 
40 
40
90
90
0
0
90


Foxtail, Green

















Kochia

60
40
0
0
0
0
0
0
0
70
20
0
0
30


Pigweed
40
0
0
0
0
0
0
0
30
 0
0
0
0
0


Ragweed
30
0
0
0
0
0
0
0
0
50
0
0
0
0


Ryegrass, Italian
 0
20
0
0
0
0
0
0
0
20
0
0
0
50











31 g ai/ha
Compounds





















Preemergence
1266
1267
1268
1269
1270
1271
1272
1273
1274
1275
1276
1277
1278
1279





Barnyardgrass
80
90
90
70
70
90
90
60
30
70
90
80
80
0


Foxtail, Giant
90
90
70
90
90
80
90
80
80
90
90
90
100
0


Foxtail, Green

















Kochia

40
0
0
0
40
30
0
0
30
0
30
0
30
0


Pigweed
20
0
0
0
0
0
0
0
30
0
0
0
0
0


Ragweed
20
0
0
0
0
0
0
0
20
0
20
0
20
0


Ryegrass, Italian
 0
0
0
0
0
70
20
0
 0
0
0
0
0
0











31 g ai/ha
Compounds





















Preemergence
1282
1283
1284
1285
1286
1287
1288
1289
1290
1291
1292
1293
1294
1295





Barnyardgrass
100
0
0
40
100
90
0
20
0
100
0
0
0
0


Foxtail, Giant
100
0
0
90
100
100
0
50
0
100
70
0
0
0


Foxtail, Green

















Kochia

30
0
0
20
0
20
0
0
0
0
60
0
0
0


Pigweed
60
0
0
0
0
0
0
0
0
0
40
0
0
0


Ragweed
0
0
0
30
0
0
0
0
0
0
0
0
0
0


Ryegrass, Italian
30
0
0
0
20
0
0
0
0
0
0
0
0
0











31 g ai/ha
Compounds





















Preemergence
1296
1297
1333
1337
1338
1339
1340
1341
1342
1343
1344
1345
1346
1347





Barnyardgrass
20
20 
40
50
90
90
90
0
60
90
0
80
40
80


Foxtail, Giant
20
0
90
40
80
80
40
10
90
100
0
90
90
100


Foxtail, Green

















Kochia

0
0
0
0
0
0
0
30
0
0
0
0
10
90


Pigweed
0
0
0
0
0
0
0
0
0
0
0
0
80
90


Ragweed
0
0
0
0
0
0
0
20
0
90
0
0
0
30


Ryegrass, Italian
0
0
0
20
0
0
0
0
0
0
0
0
10
0











31 g ai/ha
Compounds





















Preemergence
1348
1349
1350
1351
1352
1353
1354
1366
1367
1368
1369
1375
1393
1396





Barnyardgrass
90
20
90
0
80
0
0
60
0
0
0
90
40
90


Foxtail, Giant
100
100
100
0
100
80
30
50



90
80
90


Foxtail, Green








0
0
20






Kochia

0
0
30
0
20
60
0
0
0
0
0
50
40
30


Pigweed
0
0
70
0
0
0
0
0
0
0
0
0
30
70


Ragweed
80
0
50
0
0
40
20
0
0
0
50
40
30
30


Ryegrass, Italian
20
0
30
0
0
10
0
0
0
0
0
0
 0
 0













31 g ai/ha
Compounds














Preemergence
1397
1398
1399
1400
1402







Barnyardgrass
100
100
80
90
100



Foxtail, Giant
100
100
90
90
100



Foxtail, Green









Kochia

0
100
20
60
20



Pigweed
0
0
30
80
20



Ragweed
0
50
50
0
30



Ryegrass, Italian
50
0
 0
0
0











Test B


Plant species in the flooded paddy test selected from rice (Oryza sativa), sedge, umbrella (small-flower umbrella sedge, Cyperus difformis), ducksalad (Heteranthera limosa), and barnyardgrass (Echinochloa crus-galli) were grown to the 2-leaf stage for testing. At time of treatment, test pots were flooded to 3 cm above the soil surface, treated by application of test compounds directly to the paddy water, and then maintained at that water depth for the duration of the test. Treated plants and controls were maintained in a greenhouse for 13 to 15 d, after which time all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table B, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result.













TABLE B









1000 g ai/ha
Compounds













Flood
365
366
367







Barnyardgrass
0
0
0



Ducksalad
0
0
0



Rice
0
0
0



Sedge, Umbrella
0
0
0












500 g ai/ha
Compounds



















Flood
386
387
388
389
390
407
408
409
410
411
412
413





Barnyardgrass
60
50
0
60
50
60
0
40
0
20
0
0


Ducksalad
70
75
75
100
65
100
0
40
30
98
30
0


Rice
15
20
0
15
0
10
0
30
0
0
0
0


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0
0
0












500 g ai/ha
Compounds






















Flood
414
415
416
419
420
421
422
423
424
425
426
427
534
535





Barnyardgrass
0
0
0
40
65
75
0
0
0
0
0
40
0
0


Ducksalad
40
0
50
50
85
100
50
20
30
30
40
100
0
20


Rice
0
0
15
0
25
15
0
0
0
0
0
0
20
0


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0
0
0
0
50












500 g ai/ha
Compounds






















Flood
536
537
538
634
635
674
675
676
695
696
697
698
699
700





Barnyardgrass
30
30
0
20
60
60
60
80
80
75
90
50
60
85


Ducksalad
0
0
0
40
100
65
75
85
100
90
90
90
90
100


Rice
15
20
0
15
10
20
15
15
0
35
0
0
0
0


Sedge, Umbrella
0
50
0
0
0
0
0
0
0
0
0
0
0
0














500 g ai/ha
Compounds


















Flood
701
702
703
704
705
706
711
712







Barnyardgrass
65
50
30
30
0
0
0
0



Ducksalad
100
100
98
85
0
0
60
0



Rice
0
20
0
0
0
15
0
0



Sedge, Umbrella
0
0
0
0
0
0
0
0













250 g ai/ha
Compounds






















Flood
352
353
354
360
361
362
368
369
370
371
372
373
374
375





Barnyardgrass
0
0
0
0
0
0
55
20
60
60
60
60
60
70


Ducksalad
0
0
0
0
0
0
100
100
100
100
100
100
95
100


Rice
0
0
20
0
0
0
15
0
0
20
35
20
30
30


Sedge, Umbrella
0
0
20
0
0
0
0
0
30
0
0
0
0
0












250 g ai/ha
Compounds






















Flood
376
377
378
379
380
381
382
383
391
392
393
394
396
397





Barnyardgrass
70
60
70
0
0
0
0
0
40
60
65
0
40
65


Ducksalad
100
100
30
0
0
0
0
30
100
90
90
40
40
75


Rice
0
25
0
0
0
0
0
0
0
20
0
0
30
0


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0
0
0
0
0












250 g ai/ha
Compounds






















Flood
398
399
400
401
402
403
404
405
406
429
430
431
432
433





Barnyardgrass
60
65
65
70
100
75
80
70
70
65
65
40
20
70


Ducksalad
80
100
100
100
90
100
100
85
80
100
100
100
0
98


Rice
20
0
20
25
0
0
30
0
0
15
20
25
15
0


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0
0
0
0
0












250 g ai/ha
Compounds






















Flood
434
435
436
437
438
439
440
441
442
443
444
445
446
447





Barnyardgrass
70
60
60
65
85
40
70
70
75
70
75
70
75
40


Ducksalad
100
90
100
100
100
100
95
90
100
80
100
100
100
98


Rice
0
0
0
0
20
0
0
0
0
0
0
0
0
0


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0
0
0
0
0











250 g ai/ha
Compounds



















Flood
448
449
450
451
452
453
454
455
456
457
460
461





Barnyardgrass
40
40
45
0
0
30
40
75
0
0
40
60


Ducksalad
95
98
75
0
100
95
60
100
0
0
100
100


Rice
0
0
0
0
0
0
15
0
0
0
0
0


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0
0
0












250 g ai/ha
Compounds






















Flood
462
463
464
465
466
467
468
469
470
471
472
473
474
475





Barnyardgrass
40
25
70
80
0
20
35
40
0
0
60
40
30
20


Ducksalad
85
70
100
100
0
80
85
70
85
70
75
75
80
100


Rice
0
0
20
0
0
0
0
0
0
0
20
20
0
15


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0
0
0
0
0












250 g ai/ha
Compounds






















Flood
476
477
478
479
480
481
482
483
484
485
486
487
488
489





Barnyardgrass
0
0
0
0
0
0
0
0
0
0
0
75
65
65


Ducksalad
80
0
0
20
0
0
0
30
0
40
0
95
90
100


Rice
0
0
0
0
0
0
0
0
0
0
0
0
30
20


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0
0
0
0
0












250 g ai/ha
Compounds






















Flood
490
491
492
493
494
495
496
497
498
499
500
501
502
503





Barnyardgrass
50
0
65
60
20
35
60
70
45
50
0
20
0
45


Ducksalad
85
40
100
80
30
75
85
90
90
80
65
85
70
85


Rice
30
0
25
25
0
0
0
20
0
15
0
0
0
0


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0
0
0
0
0












250 g ai/ha
Compounds






















Flood
504
505
506
507
508
509
513
514
515
516
517
518
519
520





Barnyardgrass
40
0
40
0
0
0
30
50
0
0
0
0
65
65


Ducksalad
80
0
75
75
50
50
90
100
0
0
0
65
85
100


Rice
0
0
0
0
0
0
30
20
0
0
0
0
0
0


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0
0
0
0
0











250 g ai/ha
Compounds


















Flood
521
522
523
539
540
541
544
545
546
547
549





Barnyardgrass
40
40
50
65
55
35
25
0
70
0
25


Ducksalad
85
100
50
95
75
75
45
0
85
0
90


Rice
0
0
0
0
0
0
0
0
20
0
0


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0
0












250 g ai/ha
Compounds






















Flood
550
551
552
553
554
587
588
589
590
591
592
593
594
595





Barnyardgrass
55
20
60
65
55
55
30
60
60
65
55
60
70
50


Ducksalad
95
85
100
100
100
75
70
70
90
100
80
80
90
80


Rice
50
15
10
10
25
20
30
20
0
35
0
15
35
20


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0
0
0
0
70











250 g ai/ha
Compounds



















Flood
596
597
598
599
600
601
602
605
606
607
608
609





Barnyardgrass
95
0
0
0
0
40
0
0
50
0
0
45


Ducksalad
100
50
65
50
85
75
30
50
0
50
90
100


Rice
0
0
0
0
15
0
0
0
0
0
20
15


Sedge, Umbrella
0
0
0
0
0
0
0
0
40
0
0
0











250 g ai/ha
Compounds




















Flood
610
611
612
613
614
616
617
618
619
620
621
622
623





Barnyardgrass
65
85
65
80
65
70
90
85
0
10
50
70
40


Ducksalad
100
100
100
98
100
100
100
100
0
65
100
100
50


Rice
0
40
15
10
10
10
10
10
0
0
20
0
0


Sedge, Umbrella
0
0
85
75
0
0
0
0
0
0
0
0
0












250 g ai/ha
Compounds






















Flood
624
625
627
630
631
632
633
636
637
638
639
640
641
642





Barnyardgrass
70
40
0
20
0
80
90
70
80
85
80
30
70
30


Ducksalad
100
100
0
95
0
100
100
100
100
100
100
100
100
100


Rice
20
0
0
0
0
30
20
0
10
10
0
25
0
30


Sedge, Umbrella
0
0
0
0
0
50
0
0
0
0
0
0
0
0












250 g ai/ha
Compounds






















Flood
643
644
645
646
647
648
649
650
651
652
653
654
655
656





Barnyardgrass
80
85
80
80
75
20
60
80
60
40
30
35
20
50


Ducksalad
100
98
100
98
90
100
100
100
100
65
40
90
100
100


Rice
15
15
0
25
40
20
0
0
0
0
0
0
30
0


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0
0
0
0
0











250 g ai/ha
Compounds



















Flood
657
658
659
660
661
662
663
664
665
666
667
668





Barnyardgrass
40
50
60
45
80
80
70
85
70
75
75
70


Ducksalad
100
100
80
60
100
95
98
100
90
85
90
98


Rice
0
0
15
15
10
20
0
0
25
0
10
0


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0
0
0











250 g ai/ha
Compounds



















Flood
677
678
679
680
681
682
683
684
685
686
687
688





Barnyardgrass
30
40
30
20
35
0
35
0
30
35
35
35


Ducksalad
100
75
55
30
25
0
0
0
0
90
80
100


Rice
0
10
0
15
0
0
25
0
0
0
0
0


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0
0
0














250 g ai/ha
Compounds



















Flood
689
690
691
692
693
694
714
715
716







Barnyardgrass
40
50
70
0
75
0
0
0
0



Ducksalad
98
75
95
20
70
20
0
0
0



Rice
0
0
25
0
20
0
0
0
0



Sedge, Umbrella
0
0
0
0
0
0
0
0
0














125 g ai/ha
Compound



Flood
445







Barnyardgrass
65



Ducksalad
95



Rice
0



Sedge, Umbrella
0







62 g ai/ha
Compound



Flood
445







Barnyardgrass
60



Ducksalad
85



Rice
0



Sedge, Umbrella
0







31 g ai/ha
Compound



Flood
445







Barnyardgrass
35



Ducksalad
70



Rice
0



Sedge, Umbrella
0













250 g ai/ha
Compounds






















Flood
717
718
719
720
721
722
723
724
725
726
727
728
729
730





Barnyardgrass
60
40
85
30
0
0
0
0
0
55
0
0
60
75


Ducksalad
100
100
100
100
100
0
0
0
100
100
75
85
100
95


Rice
0
0
0
0
0
0
0
0
0
0
25
0
0
0


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0
0
0
0
0












250 g ai/ha
Compounds






















Flood
731
732
733
734
735
736
737
738
739
740
741
742
743
744





Barnyardgrass
60
45
20
60
60
40
0
40
60
60
0
60
65
60


Ducksalad
100
100
60
100
40
40
0
100
100
100
90
100
95
85


Rice
20
0
0
0
0
0
0
0
0
50
0
0
20
0


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0
40
0
0
0












250 g ai/ha
Compounds






















Flood
745
746
747
748
749
750
751
752
753
754
755
756
757
758





Barnyardgrass
70
0
0
0
0
0
40
0
0
0
0
50
75
45


Ducksalad
100
95
90
75
20
90
100
0
60
40
0
100
100
100


Rice
40
0
15
25
0
0
30
0
0
0
0
0
80
0


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0
0
0
0
0












250 g ai/ha
Compounds






















Flood
759
760
761
762
763
764
765
766
767
768
769
770
771
772





Barnyardgrass
0
50
0
0
0
50
40
0
0
60
0
0
90
0


Ducksalad
0
80
95
98
60
90
100
85
100
85
80
0
100
75


Rice
0
0
0
0
0
0
20
0
0
15
15
0
20
0


Sedge, Umbrella
0
0
0
0
0
0
0
60
0
0
0
0
0
0












250 g ai/ha
Compounds






















Flood
773
774
775
776
777
778
779
780
781
782
783
785
786
787





Barnyardgrass
0
0
35
80
30
0
60
20
65
65
0
40
0
0


Ducksalad
0
0
75
80
0
100
100
90
100
100
0
90
70
50


Rice
0
0
0
0
20
0
0
0
0
0
0
0
0
0


Sedge, Umbrella
0
0
65
0
0
0
0
0
0
0
0
0
40
0












250 g ai/ha
Compounds






















Flood
788
789
790
791
792
793
794
795
796
797
798
799
800
801





Barnyardgrass
20
20
40
0
0
0
40
0
70
90
75
65
95
90


Ducksalad
60
100
100
100
0
25
30
70
90
90
50
80
95
90


Rice
0
0
0
0
0
0
20
0
40
25
40
30
30
30


Sedge, Umbrella
0
0
0
0
0
25
0
0
0
0
0
0
0
40












250 g ai/ha
Compounds






















Flood
802
803
804
805
806
807
808
809
810
811
812
813
814
815





Barnyardgrass
90
90
30
0
0
95
70
0
60
20
85
70
0
65


Ducksalad
100
100
80
0
75
100
100
0
90
40
90
100
50
75


Rice
20
55
60
0
0
0
15
0
0
0
0
20
0
20


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
40
0
0
60
0












250 g ai/ha
Compounds






















Flood
816
817
818
819
820
821
822
823
824
825
826
827
828
829





Barnyardgrass
55
60
55
65
60
60
75
40
65
0
65
30
0
55


Ducksalad
75
90
80
100
75
80
85
90
95
80
100
75
30
70


Rice
30
0
0
0
0
0
0
0
0
25
0
0
0
0


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0
0
0
0
0












250 g ai/ha
Compounds






















Flood
830
831
832
833
834
835
836
837
838
839
840
841
842
843





Barnyardgrass
20
0
0
45
60
50
65
0
40
0
0
40
65
0


Ducksalad
100
70
100
85
65
70
95
70
100
70
80
80
100
20


Rice
0
0
15
0
0
20
0
0
0
0
0
0
0
0


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0
0
0
0
0












250 g ai/ha
Compounds






















Flood
844
845
846
847
848
849
850
851
852
853
854
855
856
857





Barnyardgrass
0
30
60
0
60
75
70
0
40
70
0
70
50
60


Ducksalad
0
0
60
90
100
100
90
90
40
40
0
75
75
80


Rice
0
20
0
0
0
15
0
0
0
20
0
0
0
0


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0
0
0
0
80












250 g ai/ha
Compounds






















Flood
858
859
860
861
862
863
864
865
866
867
868
869
870
871





Barnyardgrass
45
65
0
70
0
0
50
0
35
65
0
0
0
0


Ducksalad
100
100
90
100
90
0
90
60
90
100
0
60
0
0


Rice
0
0
0
50
0
0
40
30
35
30
0
0
0
0


Sedge, Umbrella
0
0
0
0
0
0
50
30
35
30
0
0
0
0












250 g ai/ha
Compounds






















Flood
872
873
874
875
876
877
878
879
880
881
882
883
885
886





Barnyardgrass
0
85
65
70
0
55
85
90
60
45
45
0
0
75


Ducksalad
85
100
100
100
85
100
100
100
100
100
100
80
60
50


Rice
0
0
0
0
0
0
0
0
0
15
0
20
0
0


Sedge, Umbrella
40
50
0
0
0
0
0
50
0
0
0
0
0
0












250 g ai/ha
Compounds






















Flood
887
888
889
890
891
892
893
894
895
896
897
898
899
900





Barnyardgrass
50
70
60
60
0
65
90
70
75
45
45
55
55
70


Ducksalad
65
75
75
90
100
80
90
100
85
25
45
70
10
40


Rice
0
0
0
0
20
0
10
0
0
20
0
0
0
0


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0
0
0
0
0












250 g ai/ha
Compounds






















Flood
901
902
903
904
905
906
907
908
909
910
911
912
913
914





Barnyardgrass
60
0
0
0
0
0
0
0
40
70
80
50
0
0


Ducksalad
60
75
0
0
0
0
50
0
70
85
75
50
90
50


Rice
0
0
0
0
0
0
0
0
0
0
0
0
0
15


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0
0
0
0
0












250 g ai/ha
Compounds






















Flood
915
916
917
918
919
920
921
922
923
924
925
926
927
928





Barnyardgrass
40
0
0
0
0
0
85
0
0
50
0
0
0
55


Ducksalad
100
100
40
30
0
0
90
0
0
70
0
0
0
80


Rice
20
0
0
15
0
0
20
0
0
0
0
0
0
0


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0
0
0
0
0












250 g ai/ha
Compounds






















Flood
929
930
931
932
933
934
935
936
937
938
939
940
941
942





Barnyardgrass
40
50
65
0
60
0
0
0
0
40
0
0
0
0


Ducksalad
60
80
60
30
60
60
70
85
45
60
40
0
35
40


Rice
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0
0
0
0
0












250 g ai/ha
Compounds






















Flood
943
944
945
946
947
948
949
950
951
952
953
954
955
956





Barnyardgrass
0
40
0
0
0
0
30
65
30
0
20
0
70
70


Ducksalad
50
75
85
0
65
0
100
95
90
40
40
35
90
100


Rice
0
0
0
0
0
0
15
0
0
0
0
0
0
0


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0
0
0
0
0












250 g ai/ha
Compounds






















Flood
957
958
959
960
961
962
963
964
965
966
967
968
969
970





Barnyardgrass
30
55
60
20
40
60
65
0
20
0
0
0
0
0


Ducksalad
100
100
100
100
100
90
90
75
85
60
35
30
0
0


Rice
0
15
20
0
20
10
0
15
0
0
0
0
0
0


Sedge, Umbrella
0
0
0
65
0
0
0
0
0
0
0
0
0
0












250 g ai/ha
Compounds






















Flood
971
972
973
974
975
976
977
978
979
980
981
982
983
984





Barnyardgrass
60
80
0
60
40
65
15
65
60
60
0
75
30
55


Ducksalad
85
85
100
100
90
95
100
100
100
0
0
100
100
85


Rice
45
50
0
15
0
20
15
30
0
30
0
20
0
15


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0
0
0
0
0












250 g ai/ha
Compounds






















Flood
985
986
987
988
989
990
991
992
993
994
995
996
997
998





Barnyardgrass
0
55
90
75
15
50
0
0
70
75
25
0
0
0


Ducksalad
40
75
75
100
100
100
40
0
85
100
70
70
0
0


Rice
0
20
35
20
0
55
15
0
40
20
0
0
0
0


Sedge, Umbrella
0
0
0
0
0
0
0
0
60
0
30
0
0
0












250 g ai/ha
Compounds






















Flood
999
1000
1001
1002
1003
1004
1005
1006
1007
1008
1009
1010
1011
1012





Barnyardgrass
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Ducksalad
85
90
0
60
0
60
0
0
0
95
0
0
0
0


Rice
0
0
0
0
0
0
0
0
0
0
0
0
0
20


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0
0
0
0
0












250 g ai/ha
Compounds






















Flood
1013
1014
1015
1016
1017
1018
1019
1020
1021
1022
1023
1024
1025
1026





Barnyardgrass
55
100
95
0
70
65
0
75
80
0
40
40
0
0


Ducksalad
100
85
90
0
90
90
0
90
98
75
65
70
0
100


Rice
70
70
40
30
30
0
0
20
15
0
20
0
0
20


Sedge, Umbrella
100
0
35
0
0
0
0
0
0
0
0
0
0
0












250 g ai/ha
Compounds






















Flood
1027
1028
1029
1030
1031
1032
1033
1034
1035
1037
1038
1039
1040
1041





Barnyardgrass
40
20
0
30
0
0
50
60
50
25
65
65
60
0


Ducksalad
100
80
85
70
0
20
100
100
100
100
100
90
75
100


Rice
30
10
0
0
0
0
0
0
0
0
0
0
0
0


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0
0
0
0
0












250 g ai/ha
Compounds






















Flood
1042
1043
1044
1045
1046
1047
1048
1049
1050
1051
1052
1053
1054
1055





Barnyardgrass
30
0
0
75
60
0
30
20
0
0
85
0
0
0


Ducksalad
75
90
0
100
100
0
50
70
85
75
100
0
0
30


Rice
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0
0
0
0
0












250 g ai/ha
Compounds






















Flood
1056
1057
1058
1059
1060
1061
1065
1066
1067
1068
1069
1070
1071
1072





Barnyardgrass
0
30
35
0
75
60
0
45
20
0
20
0
40
70


Ducksalad
0
85
0
0
90
95
100
75
85
90
35
80
98
80


Rice
20
0
25
0
20
15
0
0
0
0
0
0
0
15


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0
0
0
0
0












250 g ai/ha
Compounds






















Flood
1073
1074
1075
1076
1077
1078
1079
1080
1081
1082
1083
1084
1085
1086





Barnyardgrass
55
75
75
20
85
30
60
50
90
0
90
75
60
45


Ducksalad
100
100
100
90
90
0
30
40
80
70
95
100
30
40


Rice
15
35
35
40
15
0
20
15
40
35
40
20
25
0


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0
0
0
0
0












250 g ai/ha
Compounds






















Flood
1087
1088
1089
1090
1091
1092
1093
1094
1095
1096
1097
1098
1099
1100





Barnyardgrass
70
30
90
80
0
60
60
45
0
0
0
0
0
0


Ducksalad
30
75
85
95
0
85
80
0
50
65
0
90
100
75


Rice
25
0
0
0
0
0
0
0
0
0
0
0
0
0


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0
0
0
0
0












250 g ai/ha
Compounds






















Flood
1101
1102
1103
1104
1105
1106
1107
1108
1109
1110
1111
1112
1113
1114





Barnyardgrass
30
60
75
40
50
70
0
40
85
90
20
0
0
45


Ducksalad
60
85
90
100
100
100
80
85
90
100
70
0
30
85


Rice
0
0
25
20
20
40
0
20
50
50
0
15
20
0


Sedge, Umbrella
0
0
0
0
0
0
0
75
0
0
0
40
0
0












250 g ai/ha
Compounds






















Flood
1115
1116
1117
1118
1119
1120
1121
1122
1123
1124
1125
1126
1127
1129





Barnyardgrass
45
50
60
65
60
65
70
70
70
0
70
75
0
20


Ducksalad
90
100
100
100
100
100
100
100
100
95
100
100
100
70


Rice
30
20
20
40
20
20
10
25
25
0
0
0
0
0


Sedge, Umbrella
0
75
0
0
50
0
0
30
0
0
0
0
0
0












250 g ai/ha
Compounds






















Flood
1130
1131
1132
1133
1134
1135
1136
1137
1138
1139
1140
1141
1142
1143





Barnyardgrass
0
60
60
50
0
0
0
0
60
0
75
50
0
0


Ducksalad
0
70
90
85
0
40
85
0
75
30
100
90
0
0


Rice
0
30
15
0
0
0
0
0
0
20
0
0
0
0


Sedge, Umbrella
0
0
40
0
0
0
0
0
0
0
0
0
0
0












250 g ai/ha
Compounds






















Flood
1144
1145
1146
1147
1148
1149
1150
1151
1152
1153
1154
1155
1156
1157





Barnyardgrass
85
75
45
0
50
45
0
0
0
30
30
50
40
55


Ducksalad
100
60
0
0
70
75
0
0
0
70
100
100
100
98


Rice
20
30
0
15
60
30
0
0
0
0
30
20
20
0


Sedge, Umbrella
0
40
50
0
0
0
0
0
0
0
0
0
0
0












250 g ai/ha
Compounds






















Flood
1158
1159
1160
1161
1162
1163
1164
1165
1166
1167
1168
1169
1170
1171





Barnyardgrass
60
0
0
0
35
30
40
95
40
0
40
0
30
30


Ducksalad
80
70
80
0
80
95
95
90
30
0
0
0
40
0


Rice
0
0
20
15
15
0
0
45
25
0
30
0
0
0


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0
0
0
0
0












250 g ai/ha
Compounds






















Flood
1172
1173
1174
1175
1176
1177
1178
1179
1180
1181
1182
1183
1184
1185





Barnyardgrass
0
60
70
65
95
70
20
0
0
0
0
95
90
60


Ducksalad
0
90
90
90
95
95
90
40
85
35
0
95
95
50


Rice
0
25
20
10
0
20
20
0
0
0
0
10
15
0


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0
0
0
0
0












250 g ai/ha
Compounds






















Flood
1186
1187
1188
1189
1190
1191
1192
1193
1194
1195
1196
1197
1198
1199





Barnyardgrass
75
60
65
75
55
0
100
75
0
20
0
70
20
40


Ducksalad
60
85
100
100
90
90
95
90
0
0
30
100
40
95


Rice
30
0
15
15
40
10
30
30
0
20
0
0
0
0


Sedge, Umbrella
0
0
0
0
0
0
30
0
0
0
0
0
30
0












250 g ai/ha
Compounds






















Flood
1200
1201
1202
1203
1204
1205
1206
1207
1208
1209
1210
1211
1212
1213





Barnyardgrass
0
0
0
30
70
40
0
0
45
0
50
85
0
70


Ducksalad
0
50
100
100
100
100
95
100
95
50
30
100
95
100


Rice
0
0
0
0
0
20
15
0
15
0
20
60
0
20


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0
0
0
0
0












250 g ai/ha
Compounds






















Flood
1214
1215
1216
1217
1218
1219
1220
1221
1222
1223
1224
1225
1226
1227





Barnyardgrass
70
0
0
0
0
0
70
85
0
80
0
80
60
0


Ducksalad
100
70
0
40
40
60
95
100
65
90
70
100
100
80


Rice
15
0
0
25
0
0
10
0
15
30
0
20
20
15


Sedge, Umbrella
60
0
0
0
0
40
0
0
70
0
0
0
0
0












250 g ai/ha
Compounds






















Flood
1228
1229
1230
1231
1232
1233
1234
1235
1236
1237
1238
1239
1240
1241





Barnyardgrass
50
50
25
85
55
80
90
100
65
0
0
40
0
0


Ducksalad
100
90
70
100
95
100
100
90
100
65
0
100
0
0


Rice
30
0
0
0
0
15
75
80
35
0
0
20
0
0


Sedge, Umbrella
0
0
0
0
0
0
0
75
0
0
0
0
0
0












250 g ai/ha
Compounds






















Flood
1242
1243
1244
1245
1246
1247
1248
1249
1250
1251
1252
1253
1254
1255





Barnyardgrass
0
0
20
0
0
20
15
60
50
0
65
40
60
65


Ducksalad
75
0
30
90
100
55
70
100
100
90
100
100
100
100


Rice
0
0
0
0
0
0
0
0
0
0
30
0
0
0


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0
0
0
0
0












250 g ai/ha
Compounds






















Flood
1256
1257
1258
1259
1260
1261
1262
1263
1264
1265
1266
1267
1268
1269





Barnyardgrass
0
20
40
0
80
75
65
0
0
60
60
90
85
60


Ducksalad
50
0
0
0
100
100
100
30
0
90
100
90
95
90


Rice
0
0
0
0
50
50
10
0
0
45
50
0
20
0


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0
0
0
0
0












250 g ai/ha
Compounds






















Flood
1270
1271
1272
1273
1274
1275
1276
1277
1278
1279
1280
1281
1282
1283





Barnyardgrass
60
40
50
30
20
75
65
40
60
40
0
0
90
0


Ducksalad
80
90
80
90
100
90
90
60
90
100
0
50
100
0


Rice
15
0
20
0
0
20
25
25
35
30
0
0
30
0


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0
0
0
0
0












250 g ai/ha
Compounds






















Flood
1284
1285
1286
1287
1288
1289
1290
1291
1292
1293
1294
1295
1296
1297





Barnyardgrass
0
60
70
75
0
0
0
90
0
0
0
0
15
0


Ducksalad
0
90
95
80
0
0
0
100
0
0
0
0
0
0


Rice
0
25
0
15
0
0
10
30
15
0
0
0
30
30


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0
0
0
0
0












250 g ai/ha
Compounds






















Flood
1298
1299
1300
1301
1302
1303
1304
1305
1306
1307
1308
1309
1310
1311





Barnyardgrass
50
65
65
0
20
0
0
20
20
30
65
60
30
80


Ducksalad
80
85
80
20
80
0
0
70
100
100
100
100
80
100


Rice
15
20
25
0
15
0
0
0
0
20
40
20
15
0


Sedge, Umbrella
0
40
0
0
0
0
0
0
0
0
0
0
0
0












250 g ai/ha
Compounds






















Flood
1312
1313
1314
1316
1317
1318
1319
1320
1321
1323
1324
1325
1326
1327





Barnyardgrass
40
25
65
75
85
65
90
0
90
90
75
15
0
30


Ducksalad
100
70
100
90
100
85
90
50
85
85
65
100
70
100


Rice
0
0
0
0
0
0
0
0
0
10
0
0
0
0


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0
0
0
0
0












250 g ai/ha
Compounds






















Flood
1328
1329
1330
1331
1332
1333
1334
1335
1336
1337
1338
1339
1340
1341





Barnyardgrass
0
60
85
70
0
45
0
0
0
20
90
95
40
30


Ducksalad
50
70
90
20
100
80
90
0
40
20
100
100
80
90


Rice
0
0
0
0
0
20
0
0
0
20
25
60
20
0


Sedge, Umbrella
0
0
0
0
0
70
0
0
0
0
0
0
0
0












250 g ai/ha
Compounds






















Flood
1342
1343
1344
1345
1346
1347
1348
1349
1350
1351
1352
1353
1354
1358





Barnyardgrass
50
95
0
90
90
90
90
90
90
0
60
60
0
0


Ducksalad
85
98
0
95
90
98
98
95
90
40
70
40
0
0


Rice
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0
0
0
0
0












250 g ai/ha
Compounds






















Flood
1366
1370
1371
1372
1373
1374
1375
1376
1377
1378
1379
1380
1381
1382





Barnyardgrass
40
60
60
80
85
0
70
40
60
85
55
60
65
30


Ducksalad
80
70
100
85
100
0
95
70
90
95
100
100
100
90


Rice
0
20
0
40
0
20
0
0
15
45
0
0
0
0


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0
0
0
0
20












250 g ai/ha
Compounds






















Flood
1383
1384
1385
1386
1387
1388
1389
1390
1391
1392
1393
1394
1395
1396





Barnyardgrass
65
65
0
55
0
65
60
0
0
0
85
40
90
80


Ducksalad
100
100
40
100
0
80
100
50
75
30
100
75
80
100


Rice
25
40
0
0
0
0
15
0
0
0
55
10
10
25


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0
0
0
0
0













250 g ai/ha
Compounds














Flood
1397
1398
1399
1400
1402







Barnyardgrass
75
80
85
80
90



Ducksalad
100
100
100
100
95



Rice
0
15
15
0
0



Sedge, Umbrella
0
0
0
0
0











Test C


Seeds of plant species selected from blackgrass (Alopecurus myosuroides), ryegrass, Italian (Italian ryegrass, Lolium multiflorum), wheat (winter wheat, Triticum aestivum), galium (catchweed bedstraw, Galium aparine), corn (Zea mays), crabgrass, large (large crabgrass, Digitaria sanguinalis), foxtail, giant (giant foxtail, Setaria faberii), johnsongrass (Sorghum halepense), lambsquarters (Chenopodium album), morningglory (Ipomoea coccinea), nutsedge, yellow (yellow nutsedge, Cyperus esculentus), pigweed (Amaranthus retroflexus), ragweed (common ragweed, Ambrosia elatior), soybean (Glycine max), barnyardgrass (Echinochloa crus-galli), oilseed rape (Brassica napus), waterhemp (common waterhemp, Amaranthus rudis) and velvetleaf (Abutilon theophrasti) were planted into a blend of loam soil and sand and treated preemergence with test chemicals formulated in a non-phytotoxic solvent mixture which included a surfactant.


At the same time, plants selected from these crop and weed species and also kochia (Kochia scoparia), oat, wild (wild oat, Avena fatua), and chickweed (common chickweed, Stellaria media) were planted in pots containing Sunshine Redi-Earth© planting medium comprising spaghnum peat moss, vermiculite, starter nutrients and dolomitic limestone and treated with postemergence applications of test chemicals formulated in the same manner. Plants ranged in height from 2 to 18 cm (1- to 4-leaf stage) for postemergence treatments. Treated plants and controls were maintained in a greenhouse for 13 to 15 d, after which time all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table C, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result.


Plant species in the flooded paddy test consisted of rice (Oryza sativa), sedge, umbrella (small-flower umbrella sedge, Cyperus difformis), ducksalad (Heteranthera limosa), and barnyardgrass (Echinochloa crus-galli) grown to the 2-leaf stage for testing. At time of treatment, test pots were flooded to 3 cm above the soil surface, treated by application of test compounds directly to the paddy water, and then maintained at that water depth for the duration of the test. Treated plants and controls were maintained in a greenhouse for 13 to 15 d, after which time all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table C, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result.












TABLE C








Compounds

Compounds


















250 g ai/ha
596
635
639
640
641
125 g ai/ha
596
635
639
640
641





Postemergence





Postemergence







Barnyardgrass
65
65
85
10
65
Barnyardgrass
45
65
70
10
35


Blackgrass
10
40
10
0
0
Blackgrass
0
5
5
0
0


Chickweed
80
90
90
35
55
Chickweed
25
85
50
60
50


Corn
10
40
35
0
10
Corn
0
5
0
0
0


Crabgrass, Large
75
70
80
35
70
Crabgrass, Large
65
50
70
10
70


Foxtail, Giant
80
60
85
65
80
Foxtail, Giant
50
50
80
10
65



Galium

60
55
70
65
65

Galium

60
60
70
60
60


Johnsongrass
10
5
0
0
0
Johnsongrass
0
5
0
0
0



Kochia

60
60
85
75
40

Kochia

35
50
80
30
0


Lambsquarters
55
85
70
40
30
Lambsquarters
40
75
65
70
5


Morningglory
50
45
75
40
40
Morningglory
25
45
60
55
35


Nutsedge, Yellow
10
0
10
10
0
Nutsedge, Yellow
10
0
0
0
0


Oat, Wild
5
5
0
5
0
Oat, Wild
0
0
0
0
0


Oilseed Rape
30
80
50
60
55
Oilseed Rape
30
10
40
50
45


Pigweed
30
75
45
55
50
Pigweed
35
75
40
35
25


Ragweed
15
80
65
55
30
Ragweed
0
70
50
30
40


Ryegrass, Italian
0
20
10
5
10
Ryegrass, Italian
0
15
5
0
10


Soybean
0
10
25
5
15
Soybean
10
5
15
10
5


Velvetleaf
55
30
60
30
50
Velvetleaf
50
10
50
25



Waterhemp
30
70
25
30
30
Waterhemp
20
55
30
10
25


Wheat
0
5
0
0
0
Wheat
0
0
0
0
0














Compounds

Compounds


















62 g ai/ha
596
635
639
640
641
31 g ai/ha
596
635
639
640
641





Postemergence





Postemergence







Barnyardgrass
30
10
40
0
10
Barnyardgrass
0
0
20
0
0


Blackgrass
0
0
0
0
0
Blackgrass
0
0
0
0
0


Chickweed
20
85
40
0
0
Chickweed
20
80
40
25
0


Corn
0
0
0
0
0
Corn
0
0
0
0
0


Crabgrass, Large
65
60
70
0
50
Crabgrass, Large
30
20
60
0
10


Foxtail, Giant
20
30
60
0
10
Foxtail, Giant
10
15
35
0
0



Galium

45
50
50
55
60

Galium

40
50
50
50
40


Johnsongrass
0
0
0
0
0
Johnsongrass
0
0
0
0
0



Kochia

30
20
50
30
0

Kochia

30
40
40
20
0


Lambsquarters
35
80
75
20
15
Lambsquarters
35
75
40
30
5


Morningglory
10
40
25
40
15
Morningglory
0
25
30
35
0


Nutsedge, Yellow
0
0
0
0
0
Nutsedge, Yellow
0
0
0
0
0


Oat, Wild
0
0
0
0
0
Oat, Wild
0
0
0
0
0


Oilseed Rape
0
45
30
15
45
Oilseed Rape
0
50
30
20
20


Pigweed
10
60
45
35
0
Pigweed
10
65
10
10
0


Ragweed
0
60
10
25
0
Ragweed
0
25
0
0
0


Ryegrass, Italian
0
0
0
0
0
Ryegrass, Italian
0
0
0
0
0


Soybean
0
0
10
10
0
Soybean
0
0
0
65
0


Velvetleaf
35
0
60
70
40
Velvetleaf
35
0
35
5
40


Waterhemp
0
60
25
20
10
Waterhemp
0
35
10
5
10


Wheat
0
0
0
0
0
Wheat
0
0
0
0
0












Compounds




















250 g ai/ha
392
393
396
397
399
421
428
429
431
445
446
450
464





Preemergence















Barnyardgrass
95
95
98
98
98
95
98
98
98
95
95
95
98


Blackgrass
60
90
80
90
90
70
30
95
98
80
55
60
85


Corn
75
70
75
75
60
75
70
90
65
85
10
65
90


Crabgrass, Large
95
98
100
100
100
95
98
98
100
100
100
95
100


Foxtail, Giant
95
95
98
98
98
90
95


95
95
95




Galium



100
90
90
45

100
90
65
95
95
95


Johnsongrass
90
85



0
75
90
90
85
65
50
95


Lambsquarters
75
85
98
75
98
70
65
85
65
50
95
65
90


Morningglory
15
10
70
70
55
20
0
60
10
25
0
10
40


Nutsedge, Yellow
0
0
20
70
0
0
30
0
0
0
0
0
0


Oilseed Rape
90
85
85
85
85
35
15
90
90
55
95
60
90


Pigweed
90
90
95
95
95
60
40
100
85
60
85
80
70


Ragweed
70
65
85
70
80
60
0
75
60
35
85
60
90


Ryegrass, Italian
90
45
80
60
50
65
45
65
70
85
45
30
85


Soybean
5
30
0
20
0
10
15
10

0
25
0
0


Velvetleaf
70
80
60
45
60
40
10
45
30
10
30
50
60


Waterhemp
90
90
95
95
98
85
35
90
90
100
98
85
95


Wheat
75
70
90
70
75
40
80
60
90
65
30
60
90













Compounds






















250 g ai/ha
465
488
492
523
591
596
612
613
616
617
618
622
624
635





Preemergence
















Barnyardgrass
100
95
95
100
95
95
98
98
95
95
98
95
95
95


Blackgrass
90
85
10
90
90
90
95
95
80
90
80
85
90
90


Corn
90
85
85
85
80
35
70
85
85
80
85
80
65
85


Crabgrass, Large
100
100
95
98
95
100
100
98
95
100
100
100
98
98


Foxtail, Giant

95
95
98
95
100
95
98
95
98
95
95
95
95



Galium

98
85
85
80
80
85
90
90
90
85
90
90
85
80


Johnsongrass
85
90
90
70
85
75
90
90
90
75
85
65
25
85


Lambsquarters
100
60
50
65
70
75
70
75
60
80
75
75
60
85


Morningglory
50
60
45
35
65
20
55
50
10
40
5
20
35
50


Nutsedge, Yellow
0
0
0
40
0
0
35
20
0
35
10
0
50
25


Oilseed Rape
90
90
85
60
85
90
90
90
85
90
90
85
85
90


Pigweed
55
85
80
90
75
55
90
90
80
75
75
90
90
85


Ragweed
80
70
45
70
70
75
65
65
75
70
80
85
80
80


Ryegrass, Italian
65
65
20
20
75
45
80
95
85
90
55
70
30
40


Soybean
15
10
0
45
0
100
0
0
15
20
0
45
40
60


Velvetleaf
65
20
5
45
20
55
60
70
35
45
60
70
65
40


Waterhemp
80
80
65
80
70
65
95
90
85
80
85
90
100
85


Wheat
95
90
35
80
70
70
90
70
85
80
80
80
80
65













Compounds






















250 g ai/ha
636
637
639
640
641
644
646
651
653
662
663
665
667
695





Preemergence
















Barnyardgrass
95
95
100
95
95
98
98
100
90
100
100
100
100
90


Blackgrass
90
90
90
50
70
95
98
85
90
98
95
90
95
90


Corn
90
85
85
0
10
85
75
70
20
85
60
70
85
80


Crabgrass, Large
100
100
100
100
100
100
100
100
100
100
100
100
98
95


Foxtail, Giant
90
95
100
95
95
98
98
100
100
98
100
98
100
90



Galium

90
85
95
90
85
98
100
90
40
90
90
90
90
90


Johnsongrass
90
85
90
40
60
85
90
80
55
90
40
45
90
85


Lambsquarters
65
70
70
70
65
85
80
100
60
100
85
85
100
80


Morningglory
65
45
40
0
0
0
10
0
0
25
40
10
10
10


Nutsedge, Yellow
60
65
20
0
0
15
35
0
25
0
50
0
25
0


Oilseed Rape
90
85
90
80
90
90
90
90
85
90
80
85
90
80


Pigweed
85
85
75
80
70
70
75
85
85
80
75
50
70
70


Ragweed
80
75
80
85
45
85
70
85
60
85
85
75
80
80


Ryegrass, Italian
90
35
70
40
70
98
90
85
25
95
75
60
98
30


Soybean
0
5
20
0
100

0

40
0
0
10
0
0


Velvetleaf
55
65
55
40
45
60
60
70
50
75
55
70
40
55


Waterhemp
85
90
80
85
70
80
85
85
80
90
90
85
75
85


Wheat
75
90
85
60
70
90
90
75
40
90
90
90
50
60














Compounds

Compounds
















250 g ai/ha
697
698
700
125 g ai/ha
691
695
697
698
700





Preemergence



Preemergence







Barnyardgrass
90
90
95
Barnyardgrass
100
90
90
90
90


Blackgrass
90
70
85
Blackgrass
75
90
90
50
60


Corn
75
80
50
Corn
65
70
80
80
10


Crabgrass, Large
95
95
98
Crabgrass, Large
100
95
90
95
95


Foxtail, Giant
90
90
90
Foxtail, Giant
98
90
90
85
90



Galium

90
90
40

Galium

95
85
85
100
50


Johnsongrass
85
85
60
Johnsongrass

80
85
80
10


Lambsquarters
60
80
85
Lambsquarters
90
65
65
70
80


Morningglory
30
25
0
Morningglory
40
5
25
20
0


Nutsedge, Yellow
0
0
0
Nutsedge, Yellow
20
0
0
0
0


Oilseed Rape
85
85
50
Oilseed Rape
80
85
80
80
60


Pigweed
85
90
65
Pigweed
100
65
85
90
50


Ragweed
80
55
75
Ragweed
85
75
80
40
75


Ryegrass, Italian
50
30
45
Ryegrass, Italian
55
30
45
0
35


Soybean
10
0
0
Soybean
15
0
0
0
15


Velvetleaf
35
65
40
Velvetleaf
50
30
65
50
20


Waterhemp
85
90
70
Waterhemp
95
70
85
85
75


Wheat
35
30
70
Wheat
80
35
10
0
0












Compounds




















125 g ai/ha
392
393
396
397
399
421
428
429
431
445
446
450
464





Preemergence















Barnyardgrass
90
95
98
98
100
90
95
95
95
90
90
90
95


Blackgrass
70
70
80
90
70
70
30
90
90
80
50
45
85


Corn
55
55
65
60
65
60
55
65
50
80
0
20
75


Crabgrass, Large
95
95
98
100
100
90
98
98
100
95
100
90
100


Foxtail, Giant
95
95
98
98
98
85
90


90
90
90




Galium



100
90
90
55

100
100
45
90
90
95


Johnsongrass
85
85



0
65
95
85
80
50
20
85


Lambsquarters
75
75
70
75
85
60
35
75
50
40
55
65
80


Morningglory
0
10
60
60
30
15
0
20
10
35
0
20
20


Nutsedge, Yellow
0
0
30
50
0
0
0
0
0
0
0
0
0


Oilseed Rape
85
80
80
80
70
30
0
90
85
10
90
20
80


Pigweed
85
85
90
95
90
35
0
90
75
65
80
80
60


Ragweed
60
40
85
70
65
40
0
75
40
35
75
20
75


Ryegrass, Italian
55
30
30
60
75
35
40
85
15
50
0
0
70


Soybean
15
15
0
0
0
0
0
0
0
0
10
0
0


Velvetleaf
60
50
65
30
50
20
0
30
40
10
10
10
45


Waterhemp
90
85
95
98
90
80
10
90
85
25
80
75
80


Wheat
80
35
70
45
80
25
50
70
70
40
0
40
70













Compounds






















125 g ai/ha
465
488
492
523
591
596
610
612
613
616
617
618
622
624





Preemergence
















Barnyardgrass
98
95
90
98
95
95
95
95
95
95
95
95
90
95


Blackgrass
80
90
10
20
90
70
90
90
95
80
85
60
80
90


Corn
65
70
55
65
60
0
10
65
65
80
75
75
85
5


Crabgrass, Large
100
95
95
100
90
100
98
98
95
95
100
100
100
100


Foxtail, Giant

90
90
98
90
95
95
95
95
90
95
90
95
90



Galium

90
85
0
80
50
40
90
90
90
85
85
85
90
80


Johnsongrass
80
85
80
60
75
70
35
85
90
75
65
85
50
0


Lambsquarters
85
60
40
70
35
70
80
40
50
70
70
70
70
70


Morningglory
25
55
20
25
40
10
35
25
55
10
25
10
25
30


Nutsedge, Yellow
0
0
0
0
0
0
0
25
10
0
20
0
0
25


Oilseed Rape
85
85
85
30
30
30
80
70
90
70
90
90
85
85


Pigweed
60
70
75
90
60
40
85
90
85
80
45
60
85
85


Ragweed
75
40
35
40
35
50
70
55
40
50
40
65
85
75


Ryegrass, Italian
65
70
25
5
35
30
30
50
75
90
50
45
35
30


Soybean

0
40
30
0
0

10
0
0
0
0
85
15


Velvetleaf
55
10
5
30
20
30
40
30
40
40
20
55
70
45


Waterhemp
80
75
40
65
65
25
80
90
85
85
70
65
90
90


Wheat
80
85
5
50
30
50
30
25
65
50
45
75
70
45













Compounds






















125 g ai/ha
635
636
637
639
640
641
644
646
651
653
662
663
665
667





Preemergence
















Barnyardgrass
95
95
95
95
90
90
98
98
100
80
98
98
98
98


Blackgrass
70
90
90
85
20
30
90
85
60
60
95
85
90
85


Corn
75
85
75
80
0
0
65
65
70
0
80
20
75
80


Crabgrass, Large
95
100
100
100
98
100
98
98
100
100
100
100
100
98


Foxtail, Giant
95
90
95
95
95
90
98
95
98
95
95
98
98
98



Galium

80
90
80
85
85
90
90
90
90
30
100
85
90
98


Johnsongrass
65
85
75
80
0
10
85
85
70
40
90
20
25
85


Lambsquarters
80
55
55
40
50
40
85
75
85
50
100
65
70
90


Morningglory
30
35
40
35
0
0
0
0
0
0
30
30
20
0


Nutsedge, Yellow
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Oilseed Rape
90
85
85
85
5
85
85
85
90
30
90
65
80
85


Pigweed
85
80
85
65
70
60
55
65
50
50
75
70
50
50


Ragweed
80
65
75
75
70
30
70
60
60
35
80
70
70
70


Ryegrass, Italian
20
50
30
60
5
35
65
80
75
20
80
50
65
95


Soybean
5
0
0
10
0
10
0
10
0
5
0
0
0
0


Velvetleaf
15
55
45
65
10
25
40
55
70
35
70
30
60
50


Waterhemp
85
85
85
75
70
45
65
75
50
50
85
85
65
60


Wheat
10
65
90
80
45
35
85
85
55
0
90
55
50
55












Compounds




















62 g ai/ha
392
393
396
397
399
421
428
429
431
445
446
450
464





Preemergence















Barnyardgrass
90
90
95
95
98
80
95
95
95
90
90
90
95


Blackgrass
45
55
50
70
80
45
0
90
85
65
0
0
85


Corn
65
40
50
15
40
0
25
40
35
75
0
5
70


Crabgrass, Large
95
95
98
98
98
95
95
98
100
95
100
90
100


Foxtail, Giant
95
95
98
95
95
85
90


90
90
90




Galium



90
80
85
0

100
90
0
90
90
95


Johnsongrass
85
80



0
50
95
75
80
40
0
80


Lambsquarters
70
75
75
70
85
35
10
75
40
30
50
50
80


Morningglory
0
10
40
55
40
0
0
30
10
10
0
0
20


Nutsedge, Yellow
0
0
0
10
0
0
0
0
0
0
0
0
0


Oilseed Rape
80
40
70
70
30
25
0
80
60
0
85
30
85


Pigweed
80
75
80
90
75
0
0
85
60
10
75
60
45


Ragweed
45
35
80
75
50
30
0
40
40
40
40
10
70


Ryegrass, Italian
40
30
55
60
50
40
40
85
10
40
0
0
55


Soybean
100
10
0
0
0
0
0


0
20
5
0


Velvetleaf
40
35
40
25
20
20
0
40
25
0
0
0
30


Waterhemp
85
80
90
90
80
30
0
85
75
35
100
60
75


Wheat
35
20
10
45
15
0
15
60
5
30
0
30
50













Compounds






















62 g ai/ha
465
488
492
523
591
596
610
612
613
616
617
618
622
623





Preemergence
















Barnyardgrass
95
90
90
95
90
95
90
95
95
90
90
95
95
95


Blackgrass
50
50
5
0
85
40
50
90
85
45
20
10
0
90


Corn
55
60
10
20
70
0
10
30
55
65
40
50
45
65


Crabgrass, Large
100
95
95
95
90
100
95
95
95
90
95
100
95
95


Foxtail, Giant

90
90
90
90
90
95
90
95
90
90
90
90
90



Galium

85
85
0
80
50
85
90
0
90
85
85
0
90
90


Johnsongrass
65
80
55
30
55
25
10
60
85
85
30
60
60
70


Lambsquarters
75
50
35
70
20
60
75
45
60
35
55
50
35
50


Morningglory
20
25
10
35
30
0
35
0
40
0
0
0
0
15


Nutsedge, Yellow
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Oilseed Rape
10
45
50
0
20
0
50
50
70
60
85
85
85
85


Pigweed
25
75
25
100
45
25
75
80
80
80
20
60
85
85


Ragweed
60
25
10
15
20
20
40
10
25
25
10
40
70
75


Ryegrass, Italian
70
35
5
5
10
0
0
40
25
35
45
50
50
55


Soybean

0
0
25
0
0
0
0
0
0
10
10
20
0


Velvetleaf
5
0
0
0
0
20
5
10
40
10
10
5
25
60


Waterhemp
70
40
10
65
30
0
75
85
75
80
25
60
85
90


Wheat
70
35
0
30
10
45
0
55
45
10
15
30
40
35













Compounds






















62 g ai/ha
624
635
636
637
639
640
641
644
646
651
653
662
663
665





Preemergence
















Barnyardgrass
90
90
90
90
95
90
90
95
95
98
55
98
90
95


Blackgrass
70
60
85
90
85
0
45
70
80
45
15
75
60
60


Corn
0
70
80
55
40
0
0
50
45
55
0
70
10
10


Crabgrass, Large
100
95
98
100
98
100
100
95
95
100
95
98
98
100


Foxtail, Giant
90
90
90
90
90
95
90
95
95
98
95
95
95
95



Galium

85
5
85
80
80
80
30
85
90
50
100
100
90
90


Johnsongrass
0
75
85
70
65
0
0
70
40
50
0
70
10
25


Lambsquarters
40
40
40
55
25
35
40
75
60
55
35
85
60
45


Morningglory
0
25
25
35
10
0
0
0
0
0
0
0
35
15


Nutsedge, Yellow
0
0
75
85
0
0
0
0
0
0
0
0
0
0


Oilseed Rape
80
50
60
80
60
0
85
50
80
80
0
85
20
60


Pigweed
85
70
70
80
55
50
25
55
10
40
20
60
60
60


Ragweed
55
70
65
60
60
40
25
35
30
25
5
75
55
55


Ryegrass, Italian
40
5
30
30
60
5
10
55
20
40
10
70
70
60


Soybean
0
85
75
0
0
0
0
10
0


0
10
10


Velvetleaf
30
10
50
10
30
0
35
15
25
45
25
50
15
35


Waterhemp
90
80
75
80
65
75
0
65
60
40
30
80
60
40


Wheat
35
0
45
50
65
20
0
80
80
50
0
70
50
50













Compounds

















62 g ai/ha
667
690
691
695
697
698
700






Preemergence










Barnyardgrass
95
98
98
90
90
90
85



Blackgrass
80
55
5
20
75
0
55



Corn
70
70
55
25
65
70
0



Crabgrass, Large
95
100
100
90
95
90
95



Foxtail, Giant
98
98
98
85
85
90
85




Galium

100
98
95
80
85
90
0



Johnsongrass
80


80
75
75
0



Lambsquarters
70
85
90
40
40
35
25



Morningglory
0
0
20
0
10
0
0



Nutsedge, Yellow
0
50
0
0
0
0
0



Oilseed Rape
85
80
50
40
70
30
30



Pigweed
50
90
90
60
80
85
15



Ragweed
100
80
70
70
80
40
50



Ryegrass, Italian
70
45
35
60
55
0
20



Soybean
10
0
15
0
10
0
0



Velvetleaf
30
50
40
10
25
40
0



Waterhemp
10
95
95
75
80
85
65



Wheat
10
45
60
5
0
0
0












Compounds




















31 g ai/ha
392
393
396
397
399
421
428
429
431
445
446
450
464





Preemergence















Barnyardgrass
90
90
85
90
95
60
90
85
90
85
90
90
90


Blackgrass
20
10
50
55
50
40
0
70
60
40
0
0
80


Corn
45
0
0
25
35
0
15
0
0
55
0
5
50


Crabgrass, Large
90
95
95
98
98
90
90
95
98
95
100
90
95


Foxtail, Giant
90
90
95
95
95
80
85


85
85
90




Galium



90
40
80
0

100
95
0
0
50
90


Johnsongrass
70
70



0
5
75
70
40
20
0
35


Lambsquarters
60
55
50
30
90
10
0
60
10
0
60
55
45


Morningglory
0
0
10
5
40
0
0
35
0
0
0
0
10


Nutsedge, Yellow
0
0
0
0
0
0
0
0
0
0
0
0
0


Oilseed Rape
70
0
30
20
35
10
0
80
10
0
0
30
80


Pigweed
75
70
85
55
70
0
10
75
40
0
50
55
45


Ragweed
70
35
65
20
50
0
0
0
50
35
25
5
70


Ryegrass, Italian
5
5
60
0
55
10
45
70
10
20
0
0
20


Soybean
0
10
0
0
0
0
0
0
0
100
0
0
0


Velvetleaf
10
25
40
5
30
25
0
10
25
0
10
0
40


Waterhemp
80
80
95
85
80
0
0
80
80
0
100
55
75


Wheat
10
0
5
0
0
0
45
50
5
0
0
0
45













Compounds






















31 g ai/ha
465
488
492
523
591
596
610
612
613
616
617
618
622
623





Preemergence
















Barnyardgrass
90
95
80
65
90
90
60
85
90
90
85
95
90
90


Blackgrass
20
0
0
0
30
0
50
70
85
30
20
0
0
60


Corn
40
25
0
0
45
0
20
40
40
55
0
30
5
60


Crabgrass, Large
100
90
90
90
90
95
95
98
95
90
95
100
100
95


Foxtail, Giant

85
90
85
85
90
90
90
95
90
90
90
90
90



Galium

80
80
85
0
5
30
0
80
90
90
0
0
80
85


Johnsongrass
10
70
20
0
35
20
0
40
75
60
25
20
25
50


Lambsquarters
75
20
25
20
10
10
60
45
25
25
30
50
75
60


Morningglory
5
0
0
20
10
0
25
0
40
0
0
0
0
25


Nutsedge, Yellow
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Oilseed Rape
30
40
0
0
5
0
30
30
15
60
30
60
60
30


Pigweed
10
20
0
75
10
20
35
60
70
75
10
40
75
85


Ragweed
0
0
0
5
0
10
5
10
25
25
10
40
45
45


Ryegrass, Italian
10
5
0
0
0
0
0
20
10
30
10
45
25
45


Soybean
5
0
50
10
0
0
0
0
0
0
0
0
0
0


Velvetleaf
15
0
0
0
0
10
5
0
30
0
10
0
0
5


Waterhemp
60
25
0
55
5
0
60
75
70
50
20
60
75
85


Wheat
20
35
0
0
0
15
0
20
25
0
0
20
30
40













Compounds






















31 g ai/ha
624
635
636
637
639
640
641
644
646
651
653
662
663
665





Preemergence
















Barnyardgrass
75
85
90
90
90
80
85
90
90
95
20
95
95
85


Blackgrass
50
30
90
70
40
0
0
70
80
40
0
70
20
60


Corn
0
0
60
35
5
0
0
30
35
25
0
55
0
0


Crabgrass, Large
95
90
95
95
98
95
98
95
95
98
90
98
95
98


Foxtail, Giant
85
85
85
90
90
85
90
95
95
95
85
95
95
90



Galium

50
5
85
0
85
98
0
10
90
60
0
90
90
90


Johnsongrass
0
25
80
45
20
0
0
35
35
20
0
60
0
10


Lambsquarters
35
40
40
25
20
25
0
50
40
35
15
100
70
10


Morningglory
0
0
5
10
20
0
0
0
0
0
0
0
0
0


Nutsedge, Yellow
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Oilseed Rape
75
25
80
10
0
0
80
0
15
75
0
70
30
30


Pigweed
80
70
60
70
40
40
0
0
0
35
30
70
70
0


Ragweed
25
40
20
55
5
0
0
25
20
20
0
70
50
40


Ryegrass, Italian
10
0
70
55
25
0
0
50
30
15
0
50
10
30


Soybean
0
20
0
0
0
0
0
10
0
5

0
0
10


Velvetleaf
10
0
5
0
0
0
0
5
15
25
0
35
5
20


Waterhemp
85
75
65
75
50
55
0
10
65
20
35
60
50
50


Wheat
0
0
35
60
0
0
5
30
35
50
0
35
0
15













Compounds

















31 g ai/ha
667
690
691
695
697
698
700






Preemergence










Barnyardgrass
95
95
90
90
85
75
75



Blackgrass
50
50
0
0
70
0
20



Corn
55
20
40
0
40
40
0



Crabgrass, Large
95
98
100
90
90
90
95



Foxtail, Giant
95
95
95
80
85
85
80




Galium

10
95
100
50
0
100
0



Johnsongrass
70


40
70
75
100



Lambsquarters
50
75
85
25
35
10
0



Morningglory
0
0
30
0
10
0
0



Nutsedge, Yellow
0
0
0
0
0
0
0



Oilseed Rape
35
75
35
0
20
0
0



Pigweed
40
75
85
50
75
75
0



Ragweed
25
25
100
35
60
70
10



Ryegrass, Italian
60
40
0
0
15
0
0



Soybean

0
0
0
0
35
100



Velvetleaf
5
20
25
0
0
25
0



Waterhemp
0
90
85
55
80
85
10



Wheat
0
40
10
40
0
0
0
















Compounds


Compounds

















16 g ai/ha
610
623
690
691
8 g ai/ha
623
690






Preemergence




Preemergence





Barnyardgrass
40
90
95
90
Barnyardgrass
90
85



Blackgrass
0
40
0
0
Blackgrass
0
0



Corn
0
30
10
0
Corn
10
20



Crabgrass, Large
95
90
98
98
Crabgrass, Large
90
95



Foxtail, Giant
70
90
95
95
Foxtail, Giant
85
90




Galium

30
85
90
100

Galium

90
100



Johnsongrass
0
15


Johnsongrass
50




Lambsquarters
35
30
65
70
Lambsquarters
10
65



Morningglory
0
0
0
0
Morningglory
0
0



Nutsedge, Yellow
0
0
0
0
Nutsedge, Yellow
0
0



Oilseed Rape
0
0
50
0
Oilseed Rape
80
0



Pigweed
30
85
60
35
Pigweed
75
50



Ragweed
0
20
10
0
Ragweed
0
0



Ryegrass, Italian
0
20
10
0
Ryegrass, Italian
0
0



Soybean
0
0
0
0
Soybean
0
0



Velvetleaf
0
0
0
10
Velvetleaf
0
0



Waterhemp
35
75
80
85
Waterhemp
45
65



Wheat
0
0
5
10
Wheat
20
0












Compounds




















250 g ai/ha
356
363
364
455
487
596
606
611
612
613
618
633
637





Flood















Barnyardgrass
0
0
0
50
65
85
40
75
55
60
80
70
75


Ducksalad
0
0
0
100
100
100
70
95
55
100
100
100
90


Rice
0
0
0
0
0
10
0
15
15
20
15
10
45


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0
0
0
0












Compounds

















250 g ai/ha
638
639
643
644
645
650
661
664
695
697





Flood












Barnyardgrass
75
75
90
90
75
75
85
70
70
45


Ducksalad
75
100
100
100
95
95
100
100
100
100


Rice
25
20
10
0
0
0
10
0
15
70


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0












Compounds




















125 g ai/ha
363
364
455
465
487
596
606
611
612
613
618
633
637





Flood















Barnyardgrass
0
0
0
70
20
75
20
60
0
50
75
55
60


Ducksalad
0
0
80
90
85
90
50
80
0
75
95
75
70


Rice
0
0
0
0
0
10
0
0
0
10
15
0
15


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0
0
0
0












Compounds

















125 g ai/ha
638
639
643
644
645
650
661
664
695
697





Flood












Barnyardgrass
60
70
65
75
65
60
80
70
65
45


Ducksalad
60
90
75
100
80
90
95
85
80
60


Rice
25
20
0
0
0
0
0
0
15
50


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0












Compounds




















62 g ai/ha
356
363
364
455
465
487
596
606
611
612
613
618
633





Flood















Barnyardgrass
0
0
0
0
45
15
60
0
0
0
30
50
40


Ducksalad
0
0
0
40
65
45
60
0
0
0
60
60
60


Rice
0
0
0
0
0
0
0
0
0
0
0
0
0


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0
0
0
0












Compounds


















62 g ai/ha
637
638
639
643
644
645
650
661
664
695
697





Flood













Barnyardgrass
40
55
50
35
60
40
20
70
65
60
30


Ducksalad
45
40
75
50
65
60
70
75
70
50
40


Rice
15
25
0
0
0
0
0
0
0
0
0


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0
0












Compounds




















31 g ai/ha
363
364
455
465
487
596
606
611
612
613
618
633
637





Flood















Barnyardgrass
0
0
0
25
0
0
0
0
0
0
35
10
35


Ducksalad
0
0
0
45
30
30
0
0
0
0
60
0
30


Rice
0
0
0
0
0
0
0
0
0
0
0
0
15


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0
0
0
0












Compounds

















31 g ai/ha
638
639
643
644
645
650
661
664
695
697





Flood












Barnyardgrass
45
0
0
40
30
20
25
0
20
0


Ducksalad
0
50
20
55
30
60
65
45
30
40


Rice
20
0
0
0
0
0
0
0
0
0


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0














Compound



16 g ai/ha
465






Flood




Barnyardgrass
0



Ducksalad
0



Rice
0



Sedge, Umbrella
0










Test D


Seeds of plant species selected from bluegrass (annual bluegrass, Poa annua), blackgrass (Alopecurus myosuroides), canarygrass (littleseed canarygrass, Phalaris minor), chickweed (common chickweed, Stellaria media), galium (catchweed bedstraw, Galium aparine), bromegrass, downy (downy bromegrass, Bromus tectorum), field poppy (Papaver rhoeas), field violet (Viola arvensis), foxtail, green (green foxtail, Setaria viridis), deadnettle (henbit deadnettle, Lamium amplexicaule), ryegrass, Italian (Italian ryegrass, Lolium multiflorum), kochia (Kochia scoparia), lambsquarters (Chenopodium album), oilseed rape (Brassica napus), pigweed (Amaranthus retroflexus), chamomile (scentless chamomile, Matricaria inodora), Russian thistle (Salsola kali), speedwell (bird's-eye speedwell, Veronica persica), barley, spring (spring barley, Hordeum vulgare), wheat, spring (spring wheat, Triticum aestivum), buckwheat, wild (wild buckwheat, Polygonum convolvulus), mustard, wild (wild mustard, Sinapis arvensis), oat, wild (wild oat, Avena fatua), radish, wild (wild radish, Raphanus raphanistrum), windgrass (Apera spica-venti), barley, winter (winter barley Hordeum vulgare), and wheat, winter (winter wheat, Triticum aestivum) were planted into a silt loam soil and treated preemergence with test chemicals formulated in a non-phytotoxic solvent mixture which included a surfactant.


Treated plants and controls were maintained in a controlled growth environment approximately 21 d after which time all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table D, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result.












TABLE D








Compounds

Compounds
















250 g ai/ha
623
624
636
637
125 g ai/ha
623
624
636
637





Preemergence




Preemergence






Barley, Spring
65
40
75
70
Barley, Spring
35
5
60
40


Barley, Winter
65
40
80
60
Barley, Winter
40
0
55
50


Blackgrass
70
85
75
50
Blackgrass
45
15
60
45


Bluegrass
85
65
100
100
Bluegrass
70
55
90
75


Bromegrass, Downy
65
20
80
40
Bromegrass, Downy
40
20
55
25


Buckwheat, Wild
45
50
80
80
Buckwheat, Wild
15
15
90
15


Canarygrass
85
45
95
70
Canarygrass
85
25
90
50


Chamomile
100
100
100
90
Chamomile
85
90
100
90


Chickweed
95
85
90
75
Chickweed
95
60
90
65


Deadnettle
75
70
75
65
Deadnettle
75
25
70
25


Field Poppy
100
100
100
100
Field Poppy
85
100
100
100


Field Violet
15
10
85
0
Field Violet
10
10
35
0


Foxtail, Green
98
95
100
100
Foxtail, Green
98
90
100
95



Galium

80
0
60
10

Galium

15
0
30
30



Kochia

95
85
75
85

Kochia

95
15
75
35


Lambsquarters
95
60
90
75
Lambsquarters
80
35
80
40


Mustard, Wild
85
70
85
15
Mustard, Wild
85

15
15


Oat, Wild
60
35
85
85
Oat, Wild
55
15
80
75


Oilseed Rape
75
65
65
65
Oilseed Rape
25
35
60
40


Pigweed
100
98
85
98
Pigweed
95
95
50
100


Radish, Wild
85
75
100
90
Radish, Wild
50
0
65
20


Russian Thistle
70
50
60
50
Russian Thistle
60
10
50
10


Ryegrass, Italian
65
25
80
20
Ryegrass, Italian
i 40
25
65
20


Speedwell
90
100

100
Speedwell
100
100

100


Wheat, Spring
45
40
80
70
Wheat, Spring
20
15
45
80


Wheat, Winter
40
10
65
75
Wheat, Winter
20
5
70
60


Windgrass
95
95
98
95
Windgrass
95
85
95
85














Compounds

Compounds
















62 g ai/ha
623
624
636
637
31 g ai/ha
623
624
636
637





Preemergence




Preemergence






Barley, Spring
15
0
55
20
Barley, Spring
5
0
35
0


Barley, Winter
10
0
45
0
Barley, Winter
5
0
5
0


Blackgrass
40
5
30
10
Blackgrass
30
5
25
10


Bluegrass
65
25
95
25
Bluegrass
25
10
35
5


Bromegrass, Downy
30
10
20
10
Bromegrass, Downy
15
0
10
0


Buckwheat, Wild
10
0
75
10
Buckwheat, Wild
0
0
5
0


Canarygrass
70
15
85
0
Canarygrass
25
0
65
0


Chamomile
80
95
100

Chamomile
20
0
90
0


Chickweed
95

85
5
Chickweed
65
15
85
0


Deadnettle
65
0
35
0
Deadnettle
25
0
0
0


Field Poppy
80
25
95
100
Field Poppy
80
15
90
100


Field Violet
0
10
0
0
Field Violet
0
10
0
0


Foxtail, Green
98
50
100
80
Foxtail, Green
95
40
100
75



Galium

5
0
15
20

Galium

0
0
0
0



Kochia

75
5
25
0

Kochia

25
0
5
5


Lambsquarters
60
70
70
60
Lambsquarters
55
0
35
50


Mustard, Wild
15
30
15
5
Mustard, Wild
10
15
0
5


Oat, Wild
30
5
30
30
Oat, Wild
25
0
5
20


Oilseed Rape
20
25
30
40
Oilseed Rape
15
0
10
0


Pigweed
95
80
10
90
Pigweed
75
35
0
20


Radish, Wild
15

25
20
Radish, Wild
0
0




Russian Thistle
25
30
40
0
Russian Thistle
15
0
0
0


Ryegrass, Italian
15
0
40
0
Ryegrass, Italian
0
0
15
0


Speedwell
100
90

60
Speedwell
95
90

15


Wheat, Spring
10
10
40
30
Wheat, Spring
5
5
20
5


Wheat, Winter
20
0
60
40
Wheat, Winter
5
0
5
5


Windgrass
90
25
95
25
Windgrass
85
15
85
10










Test E


Seeds of plant species selected from corn (Zea mays), soybean (Glycine max), velvetleaf (Abutilon theophrasti), lambsquarters (Chenopodium album), poinsettia, wild (wild poinsettia, Euphorbia heterophylla), pigweed, palmer (palmer pigweed, Amaranthus palmeri), waterhemp (common waterhemp, Amaranthus rudis), surinam grass (Brachiaria decumbens), crabgrass, large (large crabgrass, Digitaria sanguinalis), crabgrass, Brazil (Brazilian crabgrass, Digitaria horizontalis), panicum, fall (fall panicum, Panicum dichotomiflorum), foxtail, giant (giant foxtail, Setaria faberii), foxtail, green (green foxtail, Setaria viridis), goosegrass (Eleusine indica), johnsongrass (Sorghum halepense), ragweed (common ragweed, Ambrosia elatior), barnyardgrass (Echinochloa crus-galli), sandbur (southern sandbur, Cenchrus echinatus), arrowleaf sida (Sida rhombifolia), ryegrass, Italian (Italian ryegrass, Lolium multiflorum), dayflower, VA (Virginia dayflower, Commelina virginica), field bindweed (Convolvulus arvensis), morningglory (Ipomoea coccinea), nightshade (eastern black nightshade, Solanum ptycanthum), kochia (Kochia scoparia), nutsedge, yellow (yellow nutsedge, Cyperus esculentus), horseweed (Conyza canadensis), and beggarticks (hairy beggarticks, Bidens pilosa), were planted into a silt loam soil and treated preemergence with test chemicals formulated in a non-phytotoxic solvent mixture which included a surfactant.


At the same time, plants selected from these crop and weed species were planted in pots containing Sunshine Redi-Earth® planting medium comprising spaghnum peat moss, vermiculite, starter nutrients and dolomitic limestone and treated with postemergence applications of a test chemical formulated in the same manner. Plants ranged in height from 2 to 18 cm (1- to 4-leaf stage) for postemergence treatments. Treated plants and controls were maintained in a greenhouse for 14 to 21 d, after which time all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table E, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result.












TABLE E








Compound

Compound


250 g ai/ha
623
125 g ai/ha
623





Postemergence

Postemergence



Corn
4
Corn
1


Crabgrass, Large
55
Crabgrass, Large
30


Foxtail, Giant
69
Foxtail, Giant
78


Pigweed, Palmer
68
Pigweed, Palmer
40


Soybean
35
Soybean
19


Waterhemp
68
Waterhemp
65






Compound

Compound


62 g ai/ha
623
31 g ai/ha
623





Postemergence

Postemergence



Corn
1
Corn
0


Crabgrass, Large
10
Crabgrass, Large
10


Foxtail, Giant
56
Foxtail, Giant
54


Pigweed, Palmer
43
Pigweed, Palmer
19


Soybean
20
Soybean
0


Waterhemp
55
Waterhemp
45














Compound



16 g ai/ha
623






Postemergence




Corn
0



Crabgrass, Large
1



Foxtail, Giant
5



Pigweed, Palmer
6



Soybean
0



Waterhemp
11












Compounds













250 g ai/ha
392
596
623
624
636
637





Preemergence








Arrowleaf Sida
80
50
90
60
90
0


Barnyardgrass
95
98
98
65
98
95


Beggarticks
0
0
35
50
0
0


Corn
70
0
65
20
80
70


Crabgrass, Brazil
98
100
98
100
98
95


Crabgrass, Large
98
98
98
90
98
98


Dayflower, VA
35
35
35
50
65
20


Field Bindweed
70
15
75
10
70
35


Foxtail, Giant
98
98
95
85
95
98


Foxtail, Green
98
95
98
75
98
98


Goosegrass
95
65
98
100
95
90


Horseweed
100

90
85
95



Johnsongrass
95
35
95

98
60



Kochia

90
90
95
30
95
90


Lambsquarters
100
90
95
85
90
80


Morningglory
0
0
0
40
0
35


Nightshade
90
60
70
80
50
40


Nutsedge, Yellow
0
0
80
10
60
35



Pancium, Fall

98
90
90
60
90
95


Pigweed, Palmer
90
40
95
30
90
65


Poinsettia, Wild
20


40

25


Ragweed
65
50
85
30
0
85


Ryegrass, Italian
70
50
90
15
95
35


Sandbur
90
95
90
50
95
90


Soybean
25
0
0
10
0
35


Surinam Grass
30
95
90
70
95
90


Velvetleaf
75
35
65
20
40
35


Waterhemp
90
50
95
70
80
85












Compounds













125 g ai/ha
392
596
623
624
636
637





Preemergence








Arrowleaf Sida
65
30
85
40
80
0


Barnyardgrass
90
98
98
50
98
80


Beggarticks
0
0
0
40
0
0


Corn
50
0
75
10
80
35


Crabgrass, Brazil
98
100
98
95
98
98


Crabgrass, Large
98
98
98
80
98
98


Dayflower, VA
0
40
20
30
35
0


Field Bindweed
35
0
70
5
80
0


Foxtail, Giant
98
98
95
70
95
98


Foxtail, Green
95
95
98
65
95
95


Goosegrass
95
25
98
80
90
65


Horseweed
98

90

95



Johnsongrass
50
0
85
35
95
25



Kochia

80
80
95
0
90
90


Lambsquarters
98
80
100
50
90
90


Morningglory
0
0
0
50
0
35


Nightshade
90
0
70
80
40
25


Nutsedge, Yellow
0
0
40
0
0
0



Pancium, Fall

98
0
90
30
100
90


Pigweed, Palmer
35
0
95
20
80
0


Poinsettia, Wild
35


30

20


Ragweed
0
25
95
30

20


Ryegrass, Italian
60
35
60
10
95
35


Sandbur
60
90
90
50
90
90


Soybean
20
0
0
20
0
25


Surinam Grass
15
95
90
40
95
75


Velvetleaf
50
0
65
10
60
30


Waterhemp
70
0
95
75
70
65












Compounds













62 g ai/ha
392
596
623
624
636
637





Preemergence








Arrowleaf Sida
15
30
80
50
65
0


Barnyardgrass
70
98
95
30
95
70


Beggarticks
0
0
0
25
0
0


Corn
15
0
60
0
70
0


Crabgrass, Brazil
98
95
98
80
95
85


Crabgrass, Large
95
95
98
85
98
95


Dayflower, VA
0
40
0
0
0
0


Field Bindweed
0
0
60
10
75
0


Foxtail, Giant
95
95
95
50
95
95


Foxtail, Green
90
95
95
20
95
75


Goosegrass
90
5
98
75
80
0


Horseweed
0

90
90
90



Johnsongrass
30
0
60
0
95
0



Kochia

90
25
90

90
40


Lambsquarters
75
25
90
0
90
0


Morningglory
0
0
0
20
0
0


Nightshade
80
0
35
75
0
15


Nutsedge, Yellow
0
0
20
0
0
0



Pancium, Fall

98
0
90
0
90
35


Pigweed, Palmer
20
0
90
25
10
0


Poinsettia, Wild
0


20

0


Ragweed
0
0
90
20

0


Ryegrass, Italian
10
0
50
0
65
50


Sandbur
60
90
90
30
90
35


Soybean
0
0
0
10
0
10


Surinam Grass
0
65
90
30
90
50


Velvetleaf
20
0
50
0
35
0


Waterhemp
80
0
90
60
80
40












Compounds













31 g ai/ha
392
596
623
624
636
637





Preemergence








Arrowleaf Sida
0
35
20
50
35
0


Barnyardgrass
85
95
95
0
95
85


Beggarticks
0
0
0
20
0
0


Corn
0
0
0
0
65
0


Crabgrass, Brazil
98
100
98
80
95
75


Crabgrass, Large
90
95
98
30
98
90


Dayflower, VA
0
0
0
0
0
0


Field Bindweed
0
0
0
0
0
0


Foxtail, Giant
90
95
95
20
95
75


Foxtail, Green
65
95
95
20
95
65


Goosegrass
85
5
95
50
50
0


Horseweed
0

80
30
0
0


Johnsongrass
25
0
40
0
90
0



Kochia

85
0
90
0
85
0


Lambsquarters
75
25
90
0
90



Morningglory
0
0
0
10
0
0


Nightshade
20
0

70
0
0


Nutsedge, Yellow
0
0
0
0
0
0



Pancium, Fall

95
0
90
0
90
0


Pigweed, Palmer
0
0
75
0
0
0


Poinsettia, Wild
0


20

0


Ragweed
0
0
60
20
0
0


Ryegrass, Italian
0
0
25
0
40
0


Sandbur
0
85
90
10
90
0


Soybean
0
0
0
0
0
0


Surinam Grass
0
35
75
20
40
10


Velvetleaf
0
0
0
0
20
0


Waterhemp
35
0
90
50
25
50










Test F


Plant species in the flooded paddy test consisted of one stand of 9 or 10 water seeded rice seedlings (Rice, W. S. Jap, Oryza sativa cv. ‘Japonica—M202’ or Rice, W. S. Ind, ‘Indica’), and two stands of 3 or 4 transplanted rice seedlings (Oryza sativa cv. ‘Japonica—M202’), monochoria (Monochoria vaginalis), sedge, umbrella (small-flower umbrella sedge, Cyperus difformis), hardstem bulrush (Scirpus juncoides), redstem (purple redstem, Ammannia coccinea), rice flatsedge (Cyperus iria), bearded sprangletop (Leptochloa fascicularis), barnyardgrass (Echinochloa crus-galli), waterplantain (common waterplantain, Alisma plantago-aquatica), and late watergrass (Echinochloa oryzicola) grown to the 2 to 2.5 leaf stage for testing. Potted plants were grown in a greenhouse with day/night temperature settings of 30/27° C., and supplemental balanced lighting was provided to maintain a 16-hour photoperiod. At time of treatment, test pots were flooded to 3 cm above the soil surface, treated by application of test compounds directly to the paddy water, and then maintained at that water depth for the duration of the test. Effects of treatments on rice and weeds were visually evaluated by comparison to untreated controls after 21 d. Plant response ratings, summarized in Table F, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result.












TABLE F








Compounds

Compounds
















250 g ai/ha
465
596
617
639
250 g ai/ha
465
596
617
639





Flood




Flood






Barnyardgrass
100
100
100
100
Rice, Water Seeded
60
15
60
75


Bulrush, Hardstem




Sedge, Umbrella
0

0
0


Flatsedge, Rice
0

0
0
Sprangletop, Brdd.
95
95
90
98



Monochoria

100
100
100
100
Watergrass, Late
100
100 
100
100


Redstem
45

0
30
Waterplantain
100

90
100


Rice, Transplanted
15
 0
0
40














Compounds

Compounds
















125 g ai/ha
465
596
617
639
64 g ai/ha
465
596
617
639





Flood




Flood






Barnyardgrass
100
100
100
100
Barnyardgrass
100
100 
85
100


Bulrush, Hardstem




Bulrush, Hardstem






Flatsedge, Rice
0

0
0
Flatsedge, Rice
0

0
0



Monochoria

100
100
70
100

Monochoria

75
100 
40
98


Redstem
0

0
0
Redstem
0

0
0


Rice, Transplanted
0
 0
0
25
Rice, Transplanted
0
 0
0
15


Rice, Water Seed.
35
 10
20
50
Rice, Water Seed.
0
10
0
40


Sedge, Umbrella
0

0
0
Sedge, Umbrella
0

0
0


Sprangletop, Brdd.
95
 85
85
95
Sprangletop, Brdd.
85
85
80
85


Watergrass, Late
100
100
100
100
Watergrass, Late
00
85
100
100


Waterplantain
90

85
98
Waterplantain
40

75
80














Compounds

Compound













32 g ai/ha
465
596
617
639
16 g ai/ha
596





Flood




Flood



Barnyardgrass
100
65
60
90
Barnyardgrass
45


Bulrush, Hardstem





Monochoria

25


Flatsedge, Rice
0

0
0
Rice, Transplanted
0



Monochoria

50
45
0
65
Rice, Water Seeded
0


Redstem
0

0
0
Sprangletop, Brdd.
0


Rice, Transplanted
0
 0
0
0
Watergrass, Late
15


Rice, Water Seeded
0
 0
0
0




Sedge, Umbrella
0

0
0




Sprangletop, Brdd.
85
40
0
85




Watergrass, Late
85
40
100
100




Waterplantain
0

0
80










Test G


Pre-Emergence Protocol

Seeds of corn (Zea mays), giant foxtail (Setaria faberi), barnyardgrass (Echinochloa crus-galli), ivy-leaved morning glory (Ipomoea hederacea), redroot pigweed (Amaranthus retroflexus) and velvetleaf (Abutilon theophrasti) were sown in standard soil in pots. After cultivation for one day under controlled conditions in a glasshouse (at 24/16° C., day/night; 14 hours light; 65% humidity), the plants were sprayed with an aqueous spray solution derived from the formulation of the technical active ingredient in acetone/water (50:50) solution containing 0.5% Tween 20 (polyoxyethylene sorbitan monolaurate, CAS RN 9005-64-5) to give a final dose of 15.625, 62.5 or 250 g/ha of test compound. The test plants were then grown on under controlled conditions in a glasshouse (at 24/16C, day/night; 14 hours light; 65% humidity) and watered twice daily. After 13 days the test was evaluated (100=total damage to plant; 0=no damage to plant). A dash (-) means no test result. Results are shown below.


Post-Emergence Protocol

Seeds of corn (Zea mays), giant foxtail (Setaria faberi), barnyardgrass (Echinochloa crus-galli), ivy-leaved morning glory (Ipomoea hederacea), redroot pigweed (Amaranthus retroflexus) and velvetleaf (Abutilon theophrasti) were sown in standard soil in pots. After cultivation for 8 days under controlled conditions in a glasshouse (at 24/16° C., day/night; 14 hours light; 65% humidity), the plants were sprayed with an aqueous spray solution derived from the formulation of the technical active ingredient in acetone/water (50:50) solution containing 0.5% Tween 20 (polyoxyethylene sorbitan monolaurate, CAS RN 9005-64-5) to give a final dose of 15.625, 62.5 or 250 g/ha of test compound. The test plants were then grown on under controlled conditions in a glasshouse (at 24/16C, day/night; 14 hours light; 65% humidity) and watered twice daily. After 13 days the test was evaluated (100=total damage to plant; 0=no damage to plant). A dash (-) means no test result. Results are shown below.



















Barnyard

Foxtail,
Morningglory,
Pigweed,



Cmpd
grass
Corn
Giant
Ivy-leaved
Redroot
Velvetleaf















Pre-Emergence (250 g ai/ha)













1396
90
80
100
70
80
80


1397
90
90
90
80
80
70


1398
90
90
90
80
80
80


1399
90
60
90
60
80
70


1400
80
60
90

90
60


1401
80
20
90
20
90
70


1402
90
90
90
80
80
80


1403
0
0
0
0
0
0


1404
70
0
80
20
20
0


1405
0
0
0
0
0
0


1406
0
0
0
0
0
0


1407
90
0
90
0
0
0


1408
20
10
70
0
10
0


1409
10
0
40
0
0
0


1410
20
0
80
10
10
20


1411
0
0
0
0
0
0


1412
60
10
80
0
10
10


1413
80
0
90
0
20
0


1414
80
50
80
20
0
0


1415
70
0
80
0
10
0


1416
0
0
0
0
0
0


1417
80
0
90
30
30
0


1418
90
0
80
0
0
0


1419
90
50
90
60
70
0


1420
80
70
80
0
0
0


1421
80
10
90
0
0
0


1422
0
0
50
0
0
0


1423
30
10
70
0
0
0


1424
50
0
70
0
0
0


1425
60
0
80
0
0
0


1426
20
0
70
0
0
0


1427
0
0
0
0
0
0


1428
80
70
80
40
80
0


1429
70
0
80
0
0
50


1430
60
0
80
0
0
0


1431
0
0
0
0
0
0


1432
0
0
0
0
0
0


1433
0
0
0
0
0
0


1434
20
0
50
0
0
0


1435
0
0
0
0
0
0


1436
0
0
0
0
0
0


1437
0
0
0
0
0
0


1438
0
0
20
0
0
0


1439
40
0
50
0
0
0


1440
40
0
80
0
0
0


1441
0
0
0
0
0
0


1442
0
0
30
0
10
10


1443
0
0
0
0
0
0


1444
60
50
80
40
50
20


1445
0
0
0
0
0
0


1446
0
0
40
0
0
0


1447
10
20
60
0
0
0


1448
0
0
60
0
0
0


1449
30
0
80
0
0
0


1450
70
0
90
0
80
0


1451
0
0
0
0
0
0


1452
50
0
60
0
0
30


1453
90
0
90
0
0
20


1454
70
60
90
10
70
60


1455
90
10
90
20
0
0


1456
80
40
90
40
90
40


1457
50
0
90
0
0
0


1458
80
50
80
20
70
30


1459
60
0
80
0
60
0


1460
90
10
90
50
70
0


1461
90
0
90
0
0
0


1462
80
0
80
50
0
0


1463
90
0
90
0
0
0


1464
90
80
90
70
0
0


1465
70
0
90
0
0
0


1466
0
0
0
0
0
0


1468
80
0
90
0
0
0


1471
90
0
90
20
0
0


1472
80
20
80
0
0
0


1473
70
10
80
10
70
0


1474
80
40
90
10
20
0


1475
80
50
90
10
0
0


1476
80
50
80
0
0
0


1477
80
50
90
0
0
0


1478
30
10
40
0
0
0


1479
10
0
20
0
0
10


1480
90
80
90
70
40
10


1481
80
60
90
10
20
10


1482
80
30
90
10
10
10


1483
70
40
80
0
80
0


1484
30
30
30
0
20
0


1485
90
80
90
0
60
30


1486
90
40
90
0
60
10


1487
80
70
90
20
80
30


1488
0
0
0
0
0
0


1489
0
0
0
0
100
0


1490
80
10
90
0
0
0


1491
90
0
80
0
0
0


1492
80
0
80
0
0
0


1493
90
70
90
10
0
0


1494
90
60
80
70
30
0


1496
80
20
80
0
0
0


1497
80
10
80
20
0
0


1498
20
0
10
0
0
0


1499
90
80
80
100
0
30


1500
90
30
80
20
80
20


1501
60
0
80

0
0


1502
80
50
90
0
70
10


1503
20
0
30
0
0
0


1504
0
0
0
0
0
0


1505
20
0
30
0
0
0


1506
0
0
0
0
0
0


1507
0
0
0
0
0
0


1508
0
0
0
0
0
0


1509
0
0
0
0
0
0


1510
0
0
0
0
0
0


1511
0
0
0
0
0
0


1512
0
0
0
0
0
0


1513
0
0
0
0
0
0


1514
0
0
0
0
0
0


1515
0
0
0
0
0
0


1516
0
0
0
0
0
0


1517
90
20
80
0
60
0


1518
0
0
0
0
0
0


1519
0
0
0
0
0
0


1520
90
0
80
0
30
0


1522
0
0
0
0
0
0


1525
40
0
30
0
0
0


1526
80
10
90
0
70
0


1527
0
0
0
0
0
0


1528
0
0
0
0
0
0


1529
0
0
0
0
0
0


1530
0
0
0
0
0
0


1531
0
0
0
0
0
0


1532
0
0
0
0
0
0


1533
0
0
0
0
0
0


1534
0
0
0
0
0
0


1535
0
0
0
0
40
0


1536
0
0
0
0
0
0


1537
0
0
0
0
0
0


1538
50
0
60
70
0
0


1539
20
0
20
0
0
0


1540
0
0
0
0
40
0


1541
30
10
70
0
40
0


1542
10
0
10
0
0
0


1543
0
0
0
0
0
0


1544
0
0
0
0
0
0


1545
0
0
0
0
0
0


1546
80
40
90
40
70
0


1547
0
0
0
0
0
0


1548
0
0
0
0
0
0


1549
0
0
0
0
0
0


1550
0
0
0
0
0
0


1551
0
0
0
0
0
0


1552
0
0
0
0
0
0


1553
0
0
0
0
0
0


1554
10
0
20
0
30
0


1555
70
20
70
0
70
0


1556
0
0
0
0
20
0


1557
10
10
20
0
0
0


1558
10
0
0
0
10
0


1559
0
0
0
0
0
0


1560
10
10
10
0
0
0


1561
80
20
70
20
30
10


1562
20
0
30
0
0
0


1563
0
0
0
0
0
0


1564
0
10
0
0
0
0


1565
10
0
60
0
10
0


1566
0
0
0
0
0
0


1567
0
0
0
0
0
0


1568
0
0
0
0
0
0


1569
0
0
0
0
0
0


1570
0
0
0
0
0
0


1571
0
0
20
0
0
0


1572
0
0
0
0
0
0


1573
0
0
0
0
0
0


1574
60
0
70
0
30
0


1575
0
0
0
0
0
0


1576
90
20
70
0
20
0


1577
0
0
0
0
0
0


1578
0
10
60
0
20
10


1579
0
0
0
0
0
0


1580
0
0
0
0
0
0


1581
0
0
0
0
0
0


1582
0
0
0
0
0
0


1583
0
0
30
0
30
0


1584
90
70
90
10
60
20


1585
90
80
90
80
20
30


1586
90
30
70
10
60
30


1587
0
0
0
0
10
0


1588
90
80
90
80
70
20


1589
0
0
0
0
0
0


1590
60
0
80
0
0
0


1591
70
0
80
0
0
10


1592
50
0
70
10
30
0


1593
20
0
70
0
0
0


1594
20
10
30
0
0
0


1595
0
0
0
0
0
0


1596
70
0
80
100
60
20


1597
0
0
0
0
0
0


1598
80
70
90
40
50
60


1599
70
40
80
10
70
20


1600
0
0
0
0
0
0


1601
70
0
80
0
50
0


1602
40
0
70
0
40
10


1603
0
0
0
0
0
0


1604
0
0
0
0
0
0


1605
0
0
0
0
0
0


1606
60
10
90
10
0
0


1607
80
10
80
20
30
20


1608
0
0
0
0
20
0


1609
80
40
80
70
70
30


1610
0
0
0
0
0
0


1611
0
0
0
0
0
0


1612
0
0
0
0
0
0


1613
70
0
90
0
10
10


1614
0
0
0
0
80
70


1615
0
0
0
0
0
0


1616
60
0
90
20
60
50


1617
80
0
90
0
20
10


1618
10
20
20
20
20
10


1619
10
0
70
10
20
10


1620
0
0
0
0
0
0


1621
0
0
0
0
0
0


1622
0
0
0
0
0
0


1623
60
10
80
10
50
50


1624
80
0
80
0
20
10


1625
40
0
80
10
10
10


1626
0
0
0
0
0
0


1627
80
70
80
10
60
20


1628
70
0
80
20
50
0


1629
70
0
80
50
0
0


1630
0
0
0
0
0
0


1631
0
0
70
30
10
0


1632
0
0
0
0
0
0


1633
0
0
0
0
0
0


1634
0
0
0
0
0
0


1635
0
0
0
0
0
0


1636
30
0
60
0
0
0


1637
80
30
90
0
60
0


1638
0
0
0
0
0
0


1639
30
0
80
0
30
0


1640
0
0
0
0
0
0


1641
0
0
0
0
0
0


1642
0
10
20
0
0
0


1643
0
0
0
0
0
0


1644
0
0
0
0
0
0


1645
50
0
60
0
10
10


1646
0
0
0
0
0
0


1647
0
0
70
0
20
10


1648
0
0
0
0
0
0


1649
0
0
20
0
20
0


1650
90
80
90
0
80
50


1651
20
0
80
0
20
10


1652
0
10
30
0
0
0


1653
80
80
90
20
80
50


1654
80
20
90

0
10


1655
0
0
30
0
0
0


1656
20
0
80
0
0
0


1657
20
0
80
0
50
0


1658
0
0
0
0
0
0


1659
0
0
0
0
0
0


1660
0
0
0
0
0
0


1661
0
10
80
10
20
0


1662
0
0
0
0
0
0


1663
0
0
0
0
0
0


1664
80
80
90
0
100
20


1665
20
0
80
20
20
0


1667
20
0
20
30
0
0


1668
20
0
20

0
0


1669
10
0
60
10
20
10


1670
0
0
50
0
20
0


1671
90
80
90
70
50
60


1672
0
0
0
0
0
0


1673
0
0
0
0
0
0


1674
0
0
0
0
0
0


1675
0
0
10
0
0
0


1676
0
0
0
0
0
0


1677
10
0
70
0
0
0


1678
0
0
0
0
0
0


1679
90
60
90
10
30
60


1680
60
0
90
0
70
90


1682
0
0
0
0
0
0


1683
80
80
90
60
20
30


1684
0
10
0
0
10
0


1685
80
60
90
30
60
30


1686
70
50
90
60
60
40


1687
80
90
90
50
30
10


1688
90
70
90
10
60
50


1690
90
70
90
0
20
30


1691
80
80
90
50
30
60


1692
80
80
90
30
10
20


1693
70
40
70
20
10
10


1694
0
0
0
0
0
0


1696
80
50
90
20
20
0


1697
80
50
80
0
20
20


1698
80
70
90
20
40
20


1699
90
70
90
70
0
0


1700
70
30
90
20
0
0


1701
70
30
90
20
10
0


1702
90
90
90
40
50
70


1703
80
80
90
40
10
30


1704
80
80
80
30
0
10


1705
70
70
80
10
30
20


1706
80
40
90
0
20
10


1707
90
80
90
30
40
60


1708
60
0
90
20
0
0


1709
80
90
90
20
50
30


1710








1711
80
20
90
10
0
0


1712
90
70
90
20
10
20


1713
90
90
90
0
0
0


1714
80
10
80
10
10
0


1716
90
60
90
0
10
10


1717
90
0
90
0
20
0


1718
90
80
90
10
60
50


1719
90
60
90
0
20
0


1720








1721
80
0
90
0
0
0


1722
80
70
90
0
30
20


1723
90
60
90
10
30
10


1724
90
90
90
0
0
0


1725
70
30
80
0
20
0


1726
70
30
80
0
10
0


1727
80
0
80
10
30
0


1728
90
80
90
80
80
80


1729
0
0
0
0
0
0


1730
70
0
90
0
0
0


1731
0
0
20
0
0
0


1732
0
0
50
0
10
10


1733
70
80
90
80
80
80


1734
0
0
10
0
0
0


1735
0
0
0
0
0
0


1736
90
60
90
0
10
10


1737
0
0
0
0
0
0


1738
70
0
70
0
0
0


1739
0
0
0
0
0
0


1740
40
10
90
0
40
50


1741
70
30
90
0
30
60


1742
80
30
90
10
20
30


1743
80
80
90
70
80
80


1744
0
0
50

10
0


1745
60
0
50
10
20
0


1746
50
0
70
10
20
10


1747
80
0
70
0
10
0


1748
0
0
0
0
0
0


1749
0
0
0
0
0
0


1750
10
10
70
0
0
0


1751
0
0
10
0
10
0


1752
20
0
20
0
0
0


1753
80
60
90
80
60
0


1754
90
80
90
10
60
30


1755
90
80
90
80
70
70


1757
10
0
70
0
0
0


1760
0
0
30
0
0
0


1761
70
0
70
0
0
0


1762
80
80
80
10
20
10


1763
80
80
90
20
0
0


1764
80
70
80
20
30
30


1765
60
20
90
0
0
0


1766
80
20
70
0
0
10


1767
80
60
90
20
0
30


1768
0
0
0
0
0
0


1769
70
0
90
0
0
0


1770
70
0
80
30
10
20


1771
0
0
0
0
0
0


1772
80
60
90
60
10
40


1773
90
80
90
80
70
60


1783
90
90
90
40
40
70


1784
10
0
40
10
0
0


1785
0
0
10
0
20
0


1786
20
0
80
0
40
30


1787
90
40
90
20
20
20


1788
20
0
0
0
0
0


1789
0
10
0
0
20
20


1790
90
90
90
70
10
40


1791
90
80
90
80
10
40


1792
80
50
90
0
0
0


1793
90
40
90
10
0
30


1794
80
80
90
10
80
0


1795
80
80
90
60
30
10


1796
0
0
0
0
20
10


1797
80
70
90
20
60
70


1798
10
0
30
0
20
10


1799
70
80
90
0
40
20


1800
80
0
90
0
10
0


1801
90
80
90
40
40
20


1802
90
70
90
40
30
70


1803
90
30
90
0
40
20


1804
90
60
90
10
30
30


1805
0
0
10
0
30
20


1806
20
0
30
0
10
0


1807
0
0
0
0
0
0


1808
40
0
70
10
20
10


1809
90
90
90
80
60
50


1810
90
90
90
70
80
70


1811
90
80
90
80
80
70


1812
70
40
90
40
70
80


1813
10
0
90
20
20
30


1814
0
0
0
0
0
0


1815
0
0
40
0
0
0


1816
90
80
90
80
80
60


1817
0
0
10
0
0
0


1818
90
70
90
40
40
70


1819
90
60
90
0
20
10


1820
0
0
0
0
0
0


1821
0
0
60
0
20
0


1822
90
70
90
80
80
80


1823
0
0
0
0
0
0


1824
70
0
80
0
20
0


1825
0
0
70
0
0
0


1826
80
20
90
0
20
0


1827
90
50
90
20
0
10


1828
90
70
90
30
0
30


1829
90
60
90
0
30
20


1833
0
0
0
0
0
0


1836
80
80
90
30
50
30







Pre-Emergence (62.5 g ai/ha)













1396
90
80
90
70
80
70


1397
90
80
90
70
20
10


1398
90
80
90
60
60
60


1399
90
10
90
50
30
40


1400
80
40
90
0
80
10


1401
30
10
70
0
40
30


1402
90
80
90
70
80
70


1403
0
0
0
0
0
0


1404
20
0
70
10
0
0


1405
0
0
0
0
0
0


1406
0
0
0
0
0
0


1407
80
0
80
0
0
0


1408
0
0
20
0
0
0


1409
0
0
0
0
0
0


1410
0
0
0
0
20
10


1411
0
0
0
0
0
0


1412
30
10
50
0
20
0


1413
20
0
60
0
20
0


1414
70
20
80
0
0
0


1415
50
0
70
0
0
0


1416
0
0
0
0
0
0


1417
60
0
80
0
0
0


1418
80
0
70
0
0
0


1419
80
0
80
0
0
0


1420
70
50
80
0
0
0


1421
60
0
80
0
0
0


1422
0
0
10
0
0
0


1423
10
20
60
0
0
0


1424
10
0
40
0
0
0


1425
40
0
80
0
0
0


1426
10
0
50
0
0
0


1427
0
0
0
0
0
0


1428
60
20
80
10
0
0


1429
40
0
70
0
0
0


1430
20
0
50
0
0
0


1431
0
0
0
0
0
0


1432
0
0
0
0
0
0


1433
0
0
0
0
0
0


1434
0
0
20
0
0
0


1435
0
0
0
0
0
0


1436
0
0
0
0
0
0


1437
0
0
0
0
0
0


1438
0
0
0
0
0
0


1439
0
0
0
0
0
0


1440
10
0
50
0
0
0


1441
0
0
0
0
0
0


1442
0
0
0
0
0
0


1443
0
0
0
0
0
0


1444
30
0
80
0
40
20


1445
0
0
0
0
0
0


1446
0
0
0
0
0
0


1447
0
0
50
0
0
0


1448
0
0
20
0
0
0


1449
0
0
70
0
0
0


1450
30
0
70
0
0
0


1451
0
0
0
0
0
0


1452
0
0
0
0
0
0


1453
40
0
60
0
0
0


1454
60
10
70
10
0
20


1455
70
0
70
0
0
30


1456
60
0
80

0
0


1457
0
0
20
0
0
0


1458
80
0
80
0
0
0


1459
60
0
60
0

0


1460
70
0
80
40
40
0


1461
60
0
80
0
0
0


1462
50
0
70
0
0
0


1463
50
0
70
0
0
0


1464
90
50
90
30
0
0


1465
20
0
70
0
0
0


1466
0
0
0
0
0
0


1468
70
0
80
0
0
0


1471
70
0
80
0
0
0


1472
40
0
50
0
0
0


1473
40
0
70
0
0
0


1474
70
0
80
0
0
0


1475
70
30
80
0
0
0


1476
70
0
80
0
0
0


1477
60
40
80
0
0
0


1478
0
0
0
0
0
0


1479
0
0
20
0
0
0


1480
80
30
90
0
0
0


1481
40
30
60
0
0
0


1482
30
40
60
0
0
0


1483
40
20
60
0
40
0


1484
10
10
10
0
0
0


1485
90
70
90
0
30
0


1486
60
20
90
0
0
0


1487
90
20
90
0
0
0


1488
0
0
0
0
0
0


1489
0
0
0
0
0
0


1490
50
0
40
0
0
0


1491
20
0
50
0
0
0


1492
20
0
20
0
0
0


1493
90
0
80
0
0
0


1494
80
20
80
0
0
0


1496
40
0
50
0
0
0


1497
30
0
60
0
0
0


1498
0
0
0
0
0
0


1499
80
0
80
0
0
0


1500
90
0
80

0
0


1501
50
0
70
0
0
0


1502
60
0
90
0
20
0


1503
0
0
0
0

0


1504
0
0
0
0
0
0


1505
0
0
10

0
0


1506
0
0
0
0
0
0


1507
0
0
0
0
0
0


1508
0
0
0
0
0
0


1509
0
0
0
0
0
0


1510
0
0
0
0
0
0


1511
0
0
0
0
0
0


1512
0
0
0
0
0
0


1513
0
0
0
0
0
0


1514
0
0
0
0
0
0


1515
0
0
0
0
0
0


1516
0
0
0
0
0
0


1517
70
0
70
0
0
0


1518
0
0
0
0
0
0


1519
0
0
0
0
0
0


1520
50
0
60
0
0
0


1522
0
0
0
0
0
0


1525
0
0
10
0
0
0


1526
60
0
50

50
0


1527
0
0
0
0
0
0


1528
0
0
0
0
0
0


1529
0
0
0
0
0
0


1530
0
0
0
0
0
0


1531
0
0
0
0
0
0


1532
30
0
100
0
0
0


1533
0
0
0
0
0
0


1534
0
0
0
0
0
0


1535
0
0
0
0
20
0


1536
0
0
0
0
0
0


1537
0
0
0
0
0
0


1538
30
0
20
0
0
0


1539
10
0
10

0
0


1540
0
0
0
0
0
0


1541
0
0
0
0
0
0


1542
10
0
10
0
0
0


1543
0
0
0
0
0
0


1544
0
0
0
0
0
0


1545
0
0
0
0
0
0


1546
20
10
80
20
30
0


1547
0
0
0
0
0
0


1548
0
0
0
0
0
0


1549
0
0
0
0
0
0


1550
0
0
0
0
0
0


1551
0
0
0
0
0
0


1552
0
0
0
0
0
0


1553
0
0
0
0
0
0


1554
0
0
0
0
0
0


1555
20
0
30
0
30
0


1556
0
0
0
0
0
0


1557
0
0
0
0
0
0


1558
0
0
0
0
0
0


1559
0
0
0
0
0
0


1560
0
0
0
0
0
0


1561
50
0
60
0
20
0


1562
0
0

0
0
0


1563
0
0
0
0
0
0


1564
0
0
0
0
0
0


1565
0
0
0
0
0
0


1566
0
0
0
0
0
0


1567
0
0
0
0
0
0


1568
0
0
0
0
0
0


1569
0
0
0
0
0
0


1570
0
0
0
0
0
0


1571
0
0
0
0
0
0


1572
0
0
0
0
0
0


1573
0
0
0
0
0
0


1574
0
0
0
0
0
0


1575
0
0
0
0
0
0


1576
70
0
70
0
0
0


1577
0
0
0
0
0
0


1578
0
0
0
0
0
0


1579
0
0
0
0
0
0


1580
0
0
0
0
0
0


1581
0
0
0
0
0
0


1582
0
0
0
0
0
0


1583
0
0
0
0
0
0


1584
0
0
50
0
0
0


1585
90
80
80
30
0
0


1586
0
10
20
0
40
0


1587
0
10
0
0
0
0


1588
90
60
80
0
40
10


1589
0
0
0
0
0
0


1590
0
0
50
0
0
0


1591
50
10
70
0
0
0


1592
10
0
20
0
0
0


1593
0
0
10
0
0
0


1594
20
10
40
0
0
0


1595
0
0
0
0
0
0


1596
0
0
40
10
20
0


1597
0
0
0
0
0
0


1598
70
10
80
20
40
10


1599
70
10
60
10
40
30


1600
0
0
0
0
0
0


1601
10
0
20
0
0
0


1602
0
0
30
0
30
0


1603
0
0
0
0
0
0


1604
0
0
0
0
0
0


1605
0
0
0
0
0
0


1606
20
0
60
0
0
0


1607
40
0
80
10
20
0


1608
0
0
0
0
10
0


1609
50
10
80
20
40
10


1610
0
0
0
0
0
0


1611
0
0
0
0
0
0


1612
0
0
0
0
0
0


1613
0
0
50
0
0
0


1614
0
0
0
0
0
0


1615
0
0
0
0
0
0


1616
0
0
80
0
20
0


1617
30
0
80
0
10
0


1618
0
0
0
0
0
0


1619
0
0
0
0
0
0


1620
0
0
0
0
0
0


1621
0
0
0
0
0
0


1622
0
0
0
0
0
0


1623
30
0
60
10
10
0


1624
0
0
60
0
0
0


1625
0
0
10
10
20
0


1626
0
0
0
0
0
0


1627
40
10
80
0
50
20


1628
0
0
50
0
30
0


1629
0
10
50
40
0
0


1630
0
0
0
0
0
0


1631
0
10
10
20
20
0


1632
0
0
0
0
0
0


1633
0
0
0
0
0
0


1634
0
0
0
0
0
0


1635
0
0
0
0
0
0


1636
10
0
40
0
0
0


1637
30
0
90
0
50
0


1638
0
0
0
0
0
0


1639
10
0
60
0
20
0


1640
0
0
0
0
0
0


1641
0
0
0
0
0
0


1642
0
0
0
0
0
0


1643
0
0
0
0
0
0


1644
0
0
0
0
0
0


1645
40
0
30
0
10
0


1646
0
0
0
0
0
0


1647
0
0
0
0
0
0


1648
0
0
0
0
0
0


1649
0
0
10
0
20
0


1650
70
0
90
0
70
0


1651
0
0
20
0
10
0


1652
0
0
10
0
0
0


1653
80
30
90
0
40
10


1654
0
0
60
0
0
0


1655
0
0
0
0
0
0


1656
0
0
0
20
0
0


1657
10
0
60
0
20
0


1658
0
0
0
0
0
0


1659
0
0
0
0
0
0


1660
0
0
0
0
0
0


1661
0
0
50
0
0
0


1662
0
0
0
0
0
0


1663
0
0
0
0
0
0


1664
40
0
70
0
20
0


1665
0
0
0
0
0
0


1667
10
0
10

0
0


1668
0
0
0
0
0
0


1669
0
0
20
0
10
0


1670
0
0
20
0
0
0


1671
90
80
90
20
30
30


1672
0
0
0
0
0
0


1673
0
0
0
0
0
0


1674
0
0
0
0
0
0


1675
0
0
0
0
0
0


1676
0
0
0
0
0
0


1677
0
0
40
0
0
0


1678
0
0
0
0
0
0


1679
80
0
90

10
10


1680
20
0
60
0
20
10


1682
0
0
0
0
0
0


1683
70
50
80
10
20
10


1684
0
0
0
0
0
0


1685
70
0
70
20
10
10


1686
70
20
70
20
0
0


1687
70
40
70
40
10
0


1688
70
50
80
0
20
0


1690
80
20
80
0
0
0


1691
70
20
90
20
20
40


1692
70
60
80
0
10
0


1693
70
30
50
20
0
0


1694
0
0
0
0
0
0


1695
90
40
90

0
0


1696
70
40
80
10
0
0


1697
70
40
80
0
0
0


1698
70
30
70
0
10
10


1699
80
30
90
10
0
0


1700
50
0
80
10
0
0


1701
30
0
80
20
0
0


1702
70
70
80
30
0
10


1703
80
60
80
0
0
0


1704
70
50
80
0
20
0


1705
60
10
70
0
0
0


1706
60
10
70
0
0
0


1707
80
80
90
10
20
10


1708
30
0
80
0
0
0


1709
70
70
80
10
20
20


1710








1711
10
0
70
10
0
0


1712
80
10
90
0
0
0


1713
70
20
70
0
0
0


1714
50
0
70
0
0
0


1716
80
0
90
0
10
10


1717
40
0
90
0
10
10


1718
70
50
80
0
0
0


1719
70
10
90
0
0
0


1720








1721
50
0
60
0
0
0


1722
60
30
70
0
10
0


1723
40
0
70
0
0
0


1724
70
40
70
0
0
0


1725
50
0
50
0
0
0


1726
50
0
50
0
0
0


1727
40
0
60
0
0
0


1728
90
80
90
30
80
60


1729
0
0
0
0
0
0


1730
10
0
50
0
0
0


1731
0
0
0
0
0
0


1732
0
0
20
0
0
0


1733
20
20
80
20
70
50


1734
0
0
0
0
0
0


1735
0
0
0
0
0
0


1736
60
0
90
0
20
10


1737
0
0
0
0
0
0


1738
0
0
0
0
0
0


1739
0
0
0
0
0
0


1740
30
0
60
0
0
0


1741
40
10
90
0
20
30


1742
0
0
80
0
10
0


1743
40
20
90
60
60
50


1744
0
0
10
0
10
0


1745
0
0
10
0
0
0


1746
0
0
20
0
0
0


1747
0
0
10
0
10
0


1748
0
0
0
0
0
0


1749
0
0
0
0
0
0


1750
10
0
20
0
0
0


1751
0
0
0
0
0
0


1752
0
0
0
0
0
0


1753
70
0
80
0
0
0


1754
80
0
90
0
20
0


1755
80
60
90
20
40
20


1757
10
0
30
0
0
0


1760
0
0
0
0
0
0


1761
30
0
40
0
0
0


1762
80
30
80
10
10
0


1763
60
50
90
0
0
0


1764
70
20
70
0
10
10


1765
50
0
70
0
0
0


1766
60
10
70
0
0
0


1767
60
30
80
0
0
0


1768
0
0
0
0
0
0


1769
20
0
40
0
0
0


1770
20
0
50
0
0
0


1771
0
0
0
0
0
0


1772
10
0
80
0
0
0


1773
90
80
90
60
20
30


1783
90
80
90
10
0
10


1784
10
0
0
0
0
0


1785
0
0
0
0
0
0


1786
0
0
0
0
0
0


1787
60
20
70
0
0
10


1788
0
0
0
0
0
0


1789
0
0
0
0
0
0


1790
70
70
70
20
0
0


1791
80
70
90
20
0
10


1792
70
20
80
0
0
0


1793
70
20
90
0
0
0


1794
40
50
60
0
0
0


1795
70
40
80
10
20
0


1796
0
0
0
0
0
0


1797
60
50
80
10
0
20


1798
0
0
10
0
0
0


1799
70
70
90
0
10
0


1800
40
0
70
0
20
10


1801
80
40
90
0
20
10


1802
70
0
90
0
10
20


1803
70
0
90
0
0
0


1804
80
0
90
0
20
10


1805
0
0
0
0
10
20


1806
10
0
20
0
0
0


1807
0
0
0
0
0
0


1808
0
0
20
0
0
0


1809
80
80
90
70
0
0


1810
90
30
90
30
40
40


1811
90
70
90
20
70
50


1812
0
0
90
0
20
40


1813
0
0
10
0
0
0


1814
0
0
0
0
0
0


1815
0
0
0
0
0
0


1816
90
80
90
60
40
20


1817
0
0
0
0
0
0


1818
30
0
90
10
0
30


1819
60
0
80
0
0
0


1820
0
0
0
0
0
0


1821
0
10
10
0
0
0


1822
90
20
90
20
60
60


1823
0
0
0
0
0
0


1824
0
0
10
0
0
0


1825
0
0
20
0
0
0


1826
70
10
80
0
0
0


1827
80
0
90
0
0
0


1828
80
10
90
0
0
0


1829
70
10
80
0
0
0


1833
0
0
0
0
0
0


1836
70
10
80
20
50
0







Pre-Emergence (15.625 g ai/ha)













1396
80
70
90
0
80
40


1397
90
80
90
60
0
0


1398
80
20
90
0
20
0


1399
0
0
90
0
0
0


1400
30
20
60
0
20
10


1401
20
0
40

0
0


1402
80
60
90
40
0
0


1403
0
0
0
0
0
0


1404
0
0
0
0
0
0


1405
0
0
0
0
0
0


1406
0
0
0
0
0
0


1407
10
0
50
0
0
0


1408
0
0
0
0
0
0


1409
0
0
0
0
0
0


1410
0
0
0
0
0
0


1411
0
0
0
0
0
0


1412
0
0
10
0
20
0


1413
0
0
0
0
0
0


1414
20
0
60
0
0
0


1415
10
0
10
0
10
0


1416
0
0
0
0
0
0


1417
0
0
0
0
0
0


1418
0
0
0
0
0
0


1419
10
0
10
0
0
0


1420
60
0
70
0
0
0


1421
10
0
70
0
0
0


1422
0
0
0
0
0
0


1423
10
10
10
0
0
0


1424
0
0
0
0
0
0


1425
0
0
10
0
0
0


1426
0
0
0
0
0
0


1427
0
0
0
0
0
0


1428
50
50
70
10
0
0


1429
0
0
0
0
0
0


1430
0
0
10
0
0
0


1431
0
0
0
0
0
0


1432
0
0
0
0
0
0


1433
0
0
0
0
0
0


1434
0
0
0
0
0
0


1435
0
0
0
0
0
0


1436
0
0
0
0
0
0


1437
0
0
0
0
0
0


1438
0
0
0
0
0
0


1439
0
0
0
0
0
0


1440
0
0
0
0
0
0


1441
0
0
0
0
0
0


1442
0
0
0
0
0
0


1443
0
0
0
0
0
0


1444
10
0
50
10
0
0


1445
0
0
0
0
0
0


1446
0
0
0
0
0
0


1447
0
0
50
0
0
0


1448
0
0
0
0
0
0


1449
0
0
10
0
0
0


1450
10
0
40
0
0
0


1451
0
0
0
0
0
0


1452
0
0
0
0
0
0


1453
20
0
40
0
0



1454
20
0
50
20
0
0


1455
30
0
30
0

0


1456
20
0
60
0
0
0


1457
0
0
0
0
0
0


1458
20
0
20
0
0
0


1459
20
0
40
0
0
0


1460
0
0
10
0
0
0


1461
0
0
30
0
0
0


1462
20
0
0
0
0
0


1463
10
0
0
0
0
0


1464
80
0
80
0
0
0


1465
0
0
30
0
0
0


1466
0
0
0
0
0
0


1468
10
0
80
0
0
0


1471
10
0
40
0
0
0


1472
10
0
10
0
0
0


1473
20
0
50
10
0
0


1474
10
0
50
10
0
0


1475
10
0
70
0
0
0


1476
60
0
70
0
0
0


1477
50
20
60
0
0
0


1478
0
0
0
0
0
0


1479
0
0
0
0
0
0


1480
30
20
40
0
0
0


1481
20
30
40
0
0
0


1482
10
30
20
0
0
0


1483
40
30
30
0
20
0


1484
0
20
10
0
0
0


1485
60
40
60
0
0
0


1486
30
10
40
0
0
0


1487
30
10
80
0
0
0


1488
0
0
0
0
0
0


1489
0
0
0
0
0
0


1490
0
0
0
0
0
0


1491
0
0
0
0
0
0


1492
0
0
0
0
0
0


1493
40
0
60
0
0
0


1494
80
0
70
0
0
0


1496
0
0
0
0
0
0


1497
0
0
0
0
0
0


1498
0
0
0
0
0
0


1499
0
0
0
0

0


1500
30
0
60
0
0
0


1501
0
0
0

0
0


1502
20
0
60
0
0
0


1503
0
0
0

0
0


1504
0
0
0
0
0
0


1505
0
0
0
0
0
0


1506
0
0
0
0
0
0


1507
0
0
0
0
0
0


1508
0
0
0
0
0
0


1509
0
0
0
0
0
0


1510
0
0
0
0

0


1511
0
0
0
0
0
0


1512
0
0
0
0
0
0


1513
0
0
0
0
0
0


1514
0
0
0
0
0
0


1515
0
0
0
0
0
0


1516
0
0
0
0
0
0


1517
0
0
30
0
0
0


1518
0
0
0
0
0
0


1519
0
0
0
0
0
0


1520
20
0
20
0
0
0


1522
0
0
0
0
0
0


1525
0
0
0
0
0
0


1526
20
0
30
10
0
0


1527
0
0
0
0
0
0


1528
0
0
0
0
0
0


1529
0
0
0
0
0
0


1530
0
0
0
0
0
0


1531
0
0
0
0
0
0


1532
0
0
100
0
0
0


1533
0
0

0
0
0


1534
0
0
0
0
0
0


1535
0
0
0
0
0
0


1536
0
0
0
0
0
0


1537
0
0
0
0
0
0


1538
0
0
0
0
0
0


1539
0
0
0
0
0
0


1540
0
0
0
0
0
0


1541
0
0
0
0
0
0


1542
0
0
0

0
0


1543
0
0
0
0
0
0


1544
0
0
0
0
0
0


1545
0
0
0

0
0


1546
0
0
60
0
0
0


1547
0
0
0
0
0
0


1548
0
0
0
0
0
0


1549
0
0
0
0
0
0


1550
0
0
0
0
0
0


1551
0
0
0
0
0
0


1552
0
0
0
0
0
0


1553
0
0
0

0
0


1554
0
0
0
0
0
0


1555
0
0
0

40
0


1556
0
0
0
0
0
0


1557
0
0
0
0
0
0


1558
0
0
0
0
0
0


1559
0
0
0
0
0
0


1560
0
0
0
0
0
0


1561
30
10
30

0
0


1562
0
0


0
0


1563
0
0
0
0
0
0


1564
0
0
0
0
0
0


1565
0
0
0
0
0
0


1566
0
0
0
0
0
0


1567
0
0
0
0
0
0


1568
0
0
0
0
0
0


1569
0
0
0
0
0
0


1570
0
0
0
0
0
0


1571
0
0
0
0
0
0


1572
0
0
0
0
0
0


1573
0
0
0
0
0
0


1574
0
0
0
0
0
0


1575
0
0
0
0
0
0


1576
30
0
30
0
0
0


1577
0
0
0
0
0
0


1578
0
0
0
0
0
0


1579
0
0
0
0
0
0


1580
0
0
0
0
0
0


1581
0
0
0
0
0
0


1582
0
0
0
0
0
0


1583
0
0
0
0
0
0


1584
0
0
0
0
0
0


1585
70
0
70
0
0
0


1586
0
0
0
0
0
0


1587
0
0
0
0
0
0


1588
80
40
70
20
0
0


1589
0
0
0
0
0
0


1590
0
0
0
0
0
0


1591
0
0
0
0
0
0


1592
0
0
0
10
0
0


1593
0
0
0
0
0
0


1594
0
0
0
0
0
0


1595
0
0
0
0
0
0


1596
0
0
0
0
0
0


1597
0
0
0
0
0
0


1598
0
0
60
10
10
0


1599
0
0
20
10
0
0


1600
0
0
0
0
0
0


1601
0
0
0
0
0
0


1602
0
0
0
0
0
0


1603
0
0
0
0
0
0


1604
0
0
0
0
0
0


1605
0
0
0
0
0
0


1606
0
0
0
0
0
0


1607
0
0
50
0
0
0


1608
0
0
0
0
0
0


1609
20
0
70
10
20
10


1610
0
0
0
0
0
0


1611
0
0
0
0
0
0


1612
0
0
0
0
0
0


1613
0
0
0
0
0
0


1614
0
0
0
0
0
0


1615
0
0
0
0
0
0


1616
0
0
0
0
0
0


1617
10
0
20
0
0
0


1618
0
0
0
0
0
0


1619
0
0
0
0
0
0


1620
0
0
0
0
0
0


1621
0
0
0
0
0
0


1622
0
0
0
0
0
0


1623
10
10
20
10
10
10


1624
0
0
20
0
0
0


1625
0
0
0
0
0
0


1626
0
0
0
0
0
0


1627
0
0
70
0
0
0


1628
10
0
50
20
0
0


1629
10
0
30
10
0
0


1630
0
0
0
0
0
0


1631
0
0
0
0
0
0


1632
0
0
0
0
0
0


1633
0
0
0
0
0
0


1634
0
0
0
0
0
0


1635
0
0
0
0
0
0


1636
0
0
0
0
0
0


1637
20
0
60
0
20
0


1638
0
0
0
0
0
0


1639
0
0
30
0
0
0


1640
0
0
0
0
0
0


1641
0
0
0
0
0
0


1642
0
0
0
0
0
0


1643
0
0
0
0
0
0


1644
0
0
0
0
0
0


1645
0
0
0
0
0
0


1646
0
0
0
0
0
0


1647
0
0
0
0
0
0


1648
0
0
0
0
0
0


1649
0
0
0
0
0
0


1650
10
0
40
0
0
0


1651
0
0
0
0
0
0


1652
0
0
0
0
0
0


1653
0
0
60
0
0
0


1654
0
0
20
0
0
0


1655
0
0
0
0
0
0


1656
0
0
0
0
0
0


1657
0
0
0
0
0
0


1658
0
0
0
0
0
0


1659
0
0
0
0
0
0


1660
0
0
0
0
0
0


1661
0
0
0
0
0
0


1662
0
0
0
0
0
0


1663
0
0
0
0
0
0


1664
0
0
30
0
0
0


1665
0
0
0
0
0
0


1667
0
0
0
0
0
0


1668
0
0
0
0
0
0


1669
0
0
0
0
0
0


1670
0
0
0
0
0
0


1671
70
30
80
10
0
20


1672
0
0
0
0
0
0


1673
0
0
0
0
0
0


1674
0
0
0
0
0
0


1675
0
0
0
0
0
0


1676
0
0
0
0
0
0


1677
0
0
10
0
0
0


1678
0
0
0
0
0
0


1679
50
0
90
0
10
10


1680
0
0
20
0
20
10


1682
0
0
0
0
0
0


1683
60
30
70
0
20
0


1684
0
0
0
0
0
0


1685
30
0
40
10
0
10


1686
40
10
60
0
0
0


1687
40
0
60
0
0
0


1688
50
0
70
0
30
10


1690
50
0
70
0
0
0


1691
20
0
60
0
0
0


1692
20
0
60
0
0
0


1693
0
0
0
0
0
0


1694
0
0
0
0
0
0


1695
50
10
70
0
0
0


1696
10
0
60
10
20
10


1697
40
0
70
0
0
0


1698
60
0
70
10
0
0


1699
60
0
80
0
0
0


1700
20
0
40

0
0


1701
0
0
40
0
0
0


1702
50
20
70
0
0
0


1703
50
0
80
0
0
0


1704
40
0
50
0
0
0


1705
20
0
50
0
0
0


1706
40
0
50
0
0
0


1707
70
20
80
0
20
10


1708
20
0
60
0
0
0


1709
60
0
70
0
0
0


1710








1711
30
0
70
0
0
0


1712
60
0
80
0
10
0


1713
30
10
50
0
0
0


1714
0
0
30
0
0
0


1716
0
0
30
0
0
0


1717
0
0
60
0
0
0


1718
60
0
60
0
0
0


1719
30
0
70

0
0


1720








1721
0
10
30
0
0
0


1722
0
10
60
0
0
0


1723
10
0
60
0
0
0


1724
50
0
70
0
0
0


1725
20
0
20
0
0
0


1726
0
0
10
0
0
0


1727
30
0
50
0
0
0


1728
70
30
80
0
30
40


1729
0
0
0
0
0
0


1730
0
0
20
0
0
0


1731
0
0
0
0
0
0


1732
0
0
0
0
0
0


1733
0
0
10
0
0
0


1734
0
0
0
0
0
0


1735
0
0
0
0
0
0


1736
0
0
80
0
0
0


1737
0
0
0
0
0
0


1738
0
0
0
0
0
0


1739
0
0
0
0
0
0


1740
0
0
0
0
0
0


1741
0
0
0
0
10
0


1742
0
0
50
0
0
0


1743
30
30
30
0
20
10


1744
0
0
0
0
0
0


1745
0
0
0
0
0
0


1746
0
0
0
0
0
0


1747
0
0
0
0
0
0


1748
0
0
0
0
0
0


1749
0
0
0
0
0
0


1750
0
0
0
0
0
0


1751
0
0
0
0
0
0


1752
0
0
0
0
0
0


1753
30
0
70
0
0
0


1754
60
0
80
0
10
10


1755
70
20
80
0
0
0


1757
0
0
0
0
0
0


1760
0
0
0
0
0
0


1761
0
0
0
0
0
0


1762
70
0
70
0
0
0


1763
20
0
80
0
0
0


1764
40
0
60
0
0
0


1765
20
0
50
0
0
0


1766
10
20
30
0
0
0


1767
20
0
60
0
0
0


1768
0
0
0
0
0
0


1769
0
0
20
0
0
0


1770
0
0
0
0
0
0


1771
0
0
0
0
0
0


1772
0
0
30
0
0
0


1773
90
70
90
0
20
10


1783
50
50
80
10
0
0


1784
0
0
10
0
0
0


1785
0
0
0
0
0
0


1786
0
0
0
0
0
0


1787
50
20
60
0
0
0


1788
0
0
0
0
0
0


1789
0
0
0
0
0
0


1790
40
20
70
0
0
0


1791
70
20
80
10
0
0


1792
30
0
80
0
0
0


1793
20
0
30
0
0
0


1794
0
30
30
0
0
0


1795
30
0
60
0
0
0


1796
0
0
0
0
0
0


1797
40
10
60
0
0
0


1798
0
0
0
0
0
0


1799
10
0
50
0
0
0


1800
10
0
20
0
10
0


1801
40
10
80
0
0
0


1802
10
0
70
0
0
0


1803
20
0
70
0
30
10


1804
0
0
50
0
0
0


1805
0
0
0
0
20
0


1806
0
0
20
0
0
0


1807
0
0
0
0
0
0


1808
0
0
0
0
0
0


1809
90
60
90
10
0
0


1810
60
20
80
0
0
0


1811
80
0
90
0
30
10


1812
0
0
90
0
0
0


1813
0
0
0
0
0
0


1814
0
0
0
0
0
0


1815
0
0
0
0
0
0


1816
90
70
90
20
0
0


1817
0
0
0
0
0
0


1818
30
0
70
0
0
0


1819
0
0
20
0
0
0


1820
0
0
0
0
0
0


1821
0
0
0
0
0
0


1822
70
0
90
0
0
0


1823
0
0
0
0
0
0


1824
0
0
0
0
0
0


1825
0
0
0
0
0
0


1826
0
10
20
0
0
0


1827
0
0
40
0
0
0


1828
70
0
80
0
0
0


1829
60
0
70
0
0
0


1833
0
0
0
0
0
0


1836
10
10
50
10
0
0







Post-Emergence (250 g ai/ha)













1396
80
70
80
60
80
60


1397
80
80
80
70
60
40


1398
80
80
80
60
60
40


1399
80
30
80
70
60
40


1400
70
60
70
0
60
30


1401
50
50
70
30
30
30


1402
80
80
80
60
60
50


1403
10
20
0
0
10
0


1404
40
40
70
30
30
20


1405
0
0
0
0
0
0


1406
20
10
0
0
20
20


1407
60
20
70
30
30
20


1408
40
20
60
20
0
10


1409
30
10
40
0
10
10


1410
20
10
50
20
10
0


1411
0
0
0
0
0
0


1412
60
10
70
20
40
40


1413
60
0
70
0
20
10


1414
60
80
80
30
30
0


1415
60
20
70
20
30
20


1416
0
0
0
0
0
0


1417
60
20
70
30
30
20


1418
40
10
70
0
0
0


1419
60
20
70
10
30
0


1420
40
60
60
0
20
10


1421
20
10
50
0
0
0


1422
0
0
20
0
0
0


1423
10
10
60
0
50
0


1424
10
10
20
0
20
0


1425
20
10
50
0
40
0


1426
20
10
40
0
10
0


1427
0
0
0
0
0
0


1428
40
20
60
20
40
0


1429
20
10
40
20
80
30


1430
30
0
50
0
20
0


1431
0
0
0
0
40
10


1432
0
0
0
0
0
0


1433
0
0
0
0
0
0


1434
20
10
30
0
20
10


1435
0
10
0
0
30
0


1436
0
0
0
0
0
0


1437
0
0
0
0
0
0


1438
0
0
0
0
10
0


1439
10
10
60
0
40
0


1440
10
20
60
10
20
0


1441
0
20
20
0
0
0


1442
0
0
0
0
0
0


1443
0
0
0
0
0
0


1444
20
10
60
10
20
0


1445
0
0
0
0
0
0


1446
0
0
0
0
0
0


1447
0
10
50
0
0
0


1448
0
10
0
0
30
0


1449
30
10
60
10
30
0


1450
20
10
60
20
30
0


1451
0
0
0
0
0
0


1452
0
0
10
10
10
10


1453
10
10
50
10
0
0


1454
20
30
60
10
20
10


1455
20
20
50
20
40
10


1456
20
60
70
20
40
20


1457
10
10
50
20
0
0


1458
20
10
60
30
30
0


1459
20
10
60
20
40
0


1460
60
40
70
10
20
10


1461
50
0
70
0
0
0


1462
30
10
70
10
0
0


1463
30
10
70
20
10
20


1464
50
80
70
50
30
10


1465
20
10
70
20
0
10


1466
20
20
30
10
80
0


1468
40
10
70
10
30
10


1471
50
0
70
20
20
10


1472
50
40
70
20
10
10


1473
50
10
70
20
10
10


1474
60
40
70
50
30
20


1475
50
70
70
70
50
10


1476
60
70
70
60
10
10


1477
60
50
70
0
30
20


1478
60
20
60
10
10
0


1479
20
10
0
0
20
0


1480
80
60
70
20
10
20


1481
70
60
70
80
20
10


1482
60
30
60
0
0
10


1483
70
50
70
0
60
30


1484
40
30
30
0
20
10


1485
70
80
70
20
40
20


1486
70
60
70
0
30
10


1487
70
70
70
20
30
20


1488
20
0
30
0
0
0


1489
30
40
40
0
10
0


1490
60
40
60
30
0
20


1491
60
0
60
10
0
0


1492
60
0
60
0
0
20


1493
80
80
60
0
0
0


1494
50
80
60
50
0
30


1496
60
50
60
0
0
20


1497
60
50
60
10
0
20


1498
30
0
30
0
0
0


1499
60
80
70
40
0
20


1500
60
60
60
10
0
20


1501
60
30
60
0
0
0


1502
70
60
80
20
80
40


1503
10
10
40
0
0
0


1504
0
0
0
0
0
0


1505
20
10
30
10
0
0


1506
0
0
0
0
0
0


1507
0
0
0
0
0
0


1508
0
0
0
0
0
0


1509
0
0
0
0
0
0


1510
0
10
0
0
20
0


1511
0
0
0
0
0
0


1512
0
0
0
0
0
0


1513
0
0
0
0
0
0


1514
0
10
0
0
0
0


1515
0
0
0
0
0
0


1516
0
0
0
0
0
0


1517
70
80
60
70
20
20


1518
0
0
0
0
0
0


1519
0
0
0
0
0
0


1520
60
20
70
40
10
10


1522
0
10
0
0
0
0


1525
0
10
10
20
0
0


1526
60
10
60
20
0
10


1527
0
10
0
0
0
0


1528
0
0
0
0
0
0


1529
0
0
0
0
0
0


1530
0
0
0
0
0
0


1531
0
10
0
0
0
0


1532
0
0
0
0
0
0


1533
0
0
0
0
0
0


1534
0
0
0
10
0
10


1535
0
10
0
0
30
0


1536
0
0
0
0
0
0


1537
0
0
0
0
0
0


1538
10
10
50
0
0
0


1539
0
0
0
0
0
0


1540
0
10
0
10
20
0


1541
20
10
50
10
20
0


1542
0
0
0
0
0
0


1543
0
10
20
30
40
30


1544
0
10
0
0
0
0


1545
0
0
0
0
0
0


1546
80
50
80
30
60
10


1547
0
0
0
0
0
0


1548
0
0
0
0
0
0


1549
0
0
0
0
0
0


1550
0
30
0
0
40
0


1551
0
10
0
0
0
0


1552
0
10
0
0
0
0


1553
0
0
0
0
0
0


1554
0
0
0
0
0
0


1555
40
0
50
50
20
10


1556
20
0
0
0
0
0


1557
20
20
10
0
0
10


1558
20
0
0
0
0
0


1559
0
0
0
0
0
0


1560
20
0
20
0
20
10


1561
50
50
60
60
30
20


1562
20
0
20
0
20
0


1563
0
0
0
0
0
0


1564
20
10
10
0
10
0


1565
10
10
50
0
0
30


1566
20
0
0
0
0
0


1567
10
0
0
0
0
0


1568
20
10
0
0
0
0


1569
20
0
0
0
0
0


1570
10
0
20
10
0
0


1571
0
0
0
0
0
0


1572
0
0
40
30
20
0


1573
0
0
0
0
0
0


1574
40
0
60
40
0
0


1575
0
0
0
0
0
0


1576
70
10
70
20
0
10


1577
0
0
0
0
0
0


1578
20
10
60
30
30
20


1579
10
0
0
0
0
0


1580
0
0
0
0
0
0


1581
10
0
0
0
0
0


1582
0
0
0

0
0


1583
20
0
10
30
20
20


1584
70
0
80
10
40
20


1585
70
80
70
70
30
30


1586
50
30
70
40
40
10


1587
40
0
60
40
70
0


1588
80
80
70
50
20
40


1589
0
0
0
0
0
0


1590
30
0
80
30
0
0


1591
50
10
80
10
10
10


1592
30
10
70
60
10
10


1593
20
10
70
0
0
0


1594
20
0
20
0
0
0


1595
10
0
10
20
20
10


1596
70
10
80
20
40
10


1597
0
0
0
0
0
0


1598
70
60
80
70
70
50


1599
70
40
80
50
50
40


1600
0
0
0
0
0
0


1601
70
30
70
30
30
50


1602
40
20
80
50
70
40


1603
0
0
0
0
0
0


1604
0
0
0
0
0
0


1605
30
10
10
0
30
10


1606
50
0
80
30
100
60


1607
60
60
80
60
70
40


1608
10
20
60
40
20
0


1609
70
60
80
70
70
50


1610
0
0
0
0
0
0


1611
0
0
0
0
0
0


1612
0
0
0
0
0
0


1613
60
0
80
0
60
30


1614
0
0
0
0
80
20


1615
0
0
0
0
0
0


1616
60
0
80
20
60
30


1617
60
0
70
0
0
0


1618
0
0
0
0
0
0


1619
70
10
70
30
50
0


1620
0
0
0
0
0
0


1621
30
0
40
0
10
0


1622
0
0
0
0
0
0


1623
80
30
80
60
60
20


1624
70
10
80
20
20
10


1625
40
10
80
20
50
40


1626
0
0
0
0
0
0


1627
80
70
80
70
70
40


1628
70
50
80
50
60
20


1629
70
10
80
30
30
0


1630
0
0
0
0
0
0


1631
10
10
70
20
20
0


1632
10
0
20
0
20
0


1633
0
0
0
0
0
0


1634
0
0
20
0
0
0


1635
30
0
40
0
10
0


1636
50
0
70
0
0
0


1637
70
10
80
30
70
30


1638
0
0
0
0
0
0


1639
60
10
80
20
60
20


1640
0
0
0
0
0
0


1641
0
0
0
0
0
0


1642
10
0
70
0
20
0


1643
0
0
0
0
0
0


1644
20
0
30
40
0
0


1645
70
0
80
0
40
0


1646
0
0
20
0
0
0


1647
50
10
70
20
30
40


1648
0
0
0
0
0
0


1649
20
0
60
0
40
0


1650
80
70
80
20
80
40


1651
10
0
90
10
0
10


1652
30
0
40
0
0
0


1653
80
70
80
40
80
50


1654
60
20
80
30
30
40


1655
20
0
30
0
40
0


1656
30
0
80
0
30
20


1657
40
20
70
30
60
20


1658
20
10
20
20
40
10


1659
20
10
40
0
20
0


1660
0
0
0
0
0
0


1661
10
0
60
0
40
10


1662
0
0
0
0
0
0


1663
0
0
0
0
0
0


1664
70
80
80
30
80
20


1665
40
0
60
0
40
0


1667
10
0
20
0
0
0


1668
0
0
10
0
0
0


1669
70
0
80
60
30
0


1670
60
10
80
0
90
0


1671
80
80
80
50
50
40


1672
0
10
0
0
40
0


1673
0
0
10
0
0
0


1674
0
0
20
0
0
0


1675
0
0
20
0
0
10


1676
0
0
0
0
0
0


1677
10
0
50
0
0
0


1678
30
0
20
0
30
0


1679
90
60
80
40
50
40


1680
50
0
80
20
60
0


1682
0
0

0
0
0


1683
80
80
80
50
40
50


1684
0
0

0
0
0


1685
80
70
80
70
70
60


1686
80
60
80
70
40
40


1687
80
90
80
70
50
50


1688
90
60

60
10
10


1690
90
80
90
60
40
40


1691
70
70

30
0
20


1692
80
80
80
70
40
30


1693
80
70
80
60
60
20


1694
0
0
0
0
0
0


1696
80
70
80
60
60
10


1697
90
80
80
60
70
30


1698
80
70
80
70
60
50


1699
90
70
80
70
30
30


1700
70
40
70
60
0
0


1701
70
50
60
30
30
0


1702
80
80
80
70
40
70


1703
80
80
80
60
80
70


1704
80
80
80
70
10
20


1705
80
70
80
50
30
10


1706
80
70
80
60
20
20


1707
80
80

70
0
30


1708
80
70
60
20
0
0


1709
80
80
80
70
30
50


1710








1711
80
40
80
70
0
0


1712
90
70
80
70
20
40


1713
80
80
80
70
0
20


1714
80
50
80
60
90
40


1716
80
60
80
10
0
0


1717
70
10
80
0
0
0


1718
80
80
80
70
70
60


1719
80
60
80
20
0
0


1720








1721
80
10
80
70
0
0


1722
80
80
80
70
30
10


1723
80
70
80
40
30
20


1724
90
90
90
70
60
70


1725
70
70
80
70
60
10


1726
70
70
70
70
40
20


1727
70
10
80
50
0
10


1728
80
80
80
70
80
60


1729
0
0
0
0
0
0


1730
80
0
80
0
0
0


1731
0
0
0
0
10
0


1732
20
0
50
0
20
0


1733
80
70
80
70
80
80


1734
0
0
0
0
0
0


1735
0
0
0
0
0
0


1736
70
70
80
40
0
0


1737
0
0
0
0
0
0


1738
80
0
70
0
10
10


1739
0
0
0
0
0
0


1740
20
0

20
0
10


1741
70
0

10
0
10


1742
80
70
80
40
30
20


1743
80
60

30
50
50


1744
70
10
60
40
30
10


1745
80
0
70
40
20
0


1746
40
10
70
60
20
10


1747
80
30
80
50
20
10


1748
0
0
0
0
0
0


1749
0
0
0
0
0
0


1750
20
10
50
10
20
0


1751
0
0
10
0
10
10


1752
0
0
0
0
0
0


1753
70
80
70
60
30
30


1754
80
70

70
70
60


1755
80
80

70
30
60


1757
30
0
60
10
0
0


1760
10
10
20
20
0
10


1761
70
0
70
50
10
10


1762
80
80
80
70
10
70


1763
70
70
70
50
20
20


1764
80
70
80
70
30
60


1765
70
10
70
20
0
0


1766
80
60
80
40
20
10


1767
80
60
80
60
20
60


1768
0
0
0
0
0
0


1769
50
10
60
20
0
0


1770
70
0
70
20
40
30


1771
0
0

0
0
0


1772
30
60
80
50
10
30


1773
80
80
80
60
40
40


1783
80
80
80
70
20
50


1784
0
0
0
0
0
0


1785
0
0

0
0
0


1786
0
0

0
20
30


1787
60
60

70
70
40


1788
0
10
0
40
20
20


1789
0
10

0
20
20


1790
70
80
80
40
0
30


1791
80
80
80
70
0
20


1792
70
60
80
40
0
40


1793
80
50
80
70
0
30


1794
70
70
80
70
70
10


1795
70
70
80
70
30
20


1796
0
0
0
10
20
0


1797
80
70
80
80
80
90


1798
0
0
10
0
20
0


1799
70
70
70
30
70
10


1800
80
0
70
20
10
0


1801
70
80
80
50
40
0


1802
70
60
80
0
40
70


1803
70
0
80
10
20
0


1804
60
70
80
60
10
10


1805
0
0
40
30
40
30


1806
50
40
60
0
0
0


1807
0
0
0
0
0
0


1808
60
0
60
0
0
0


1809
80
80
80
70
50
40


1810
80
50
80
20
60
40


1811
80
80
80
70
80
50


1812
70
50
80
70
50
60


1813
0
0
20
40
20
10


1814
0
0
10
0
0
0


1815
0
0
10
0
0
0


1816
80
80
80
70
70
30


1817
0
0
0
0
0
0


1818
80
60
80
40
0
30


1819
80
20
80
50
10
0


1820
0
0
0
0
0
0


1821
0
30
30
10
70
0


1822
80
60
80
30
30
40


1823
0
0
0
0
0
0


1824
10
20
10
10
20
70


1825
0
10
50
20
10
20


1826
70
50
80
10
50
10


1827
80
60
80
10
0
40


1828
80
70
80
70
20
10


1829
70
60
80
30
60
20


1833
0
0
0
0
0
0


1836
80
70
70
40
70
50







Post-Emergence (62.5 g ai/ha)













1396
80
80
80
60
70
30


1397
80
80
80
60
30
10


1398
80
70
80
40
50
40


1399
70
0
80
30
20
40


1400
70
20
70
0
50
10


1401
20
0
60
0
0
20


1402
80
80
80
40
60
30


1403
0
10
0
0
10
0


1404
20
20
50
10
40
20


1405
0
0
0
0
0
0


1406
0
0
0
10
40
20


1407
40
10
70
20
10
20


1408
0
0
0
0
0
0


1409
10
0
0
0
0
0


1410
0
0
0
0
0
0


1411
0
0
0
0
0
0


1412
50
10
60
0
40
40


1413
50
0
70
0
10
0


1414
50
50
70
30
0
0


1415
30
10
60
10
10
0


1416
0
0
0
0
0
0


1417
40
10
70
20
10
20


1418
30
0
50
0
0
0


1419
50
10
60
20
20
10


1420
40
40
60
10
0
0


1421
20
10
40
0
0
0


1422
0
10
0
0
0
0


1423
10
0
20
0
0
0


1424
0
0
0
0
20
0


1425
20
10
40
0
30
0


1426
0
0
0
0
10
0


1427
0
0
0
0
0
0


1428
20
10
50
10
10
0


1429
10
0
30
10
0
0


1430
0
0
10
0
0
0


1431
0
0
0
0
0
0


1432
0
0
0
0
0
0


1433
0
0
0
0
0
0


1434
0
0
0
0
0
0


1435
0
0
0
0
30
0


1436
0
0
0
0
0
0


1437
0
0
0
0
0
0


1438
0
0
0
0
0
0


1439
0
10
20
0
0
0


1440
0
10
20
0
10
0


1441
0
0
0
0
0
0


1442
0
0
0
0
0
0


1443
0
0
0
0
0
0


1444
10
10
60
10
10
0


1445
0
0
0
0
0
0


1446
0
0
0
0
0
0


1447
0
10
20
0
0
0


1448
0
0
0
0
0
0


1449
10
0
20
0
0
0


1450
10
10
30
10
0
0


1451
0
0
0
0
0
0


1452
0
0
0
10
0
0


1453
10
10
50
0
0
0


1454
20
20
60
10
20
0


1455
0
10
10
0
0
0


1456
10
20
60
30
30
20


1457
10
0
20
0
0
0


1458
20
10
50
20
30
0


1459
10
10
60
0
40
0


1460
30
0
70
0
10
0


1461
30
0
70
0
0
0


1462
20
0
50
20
0
0


1463
0
10
0
0
10
10


1464
20
10
70
20
10
0


1465
10
10
60
0
0
0


1466
0
10
10
10
30
0


1468
50
10
70
0
0
0


1471
30
0
60
0
0
0


1472
30
20
50
20
10
10


1473
40
10
70
10
0
0


1474
50
30
70
50
0
0


1475
60
40
70
0
30
10


1476
50
20
70
20
0
0


1477
60
60
60
0
0
20


1478
40
10
30
0
0
0


1479
20
10
20
0
0
0


1480
70
20
70
0
0
0


1481
60
20
60
10
0
0


1482
30
30
30
0
0
0


1483
40
30
60
0
30
10


1484
20
0
10
0
0
0


1485
70
70
70
0
20
10


1486
60
10
60
0
0
0


1487
60
60
70
0
0
0


1488
20
10
0
0
0
0


1489
0
10
0
0
0
0


1490
60
30
60
0
0
0


1491
20
0
20
0
0
0


1492
30
0
40
0
0
0


1493
70
40
60
0
0
0


1494
60
30
60
40
0
0


1496
50
20
60
0
0
0


1497
60
0
60
0
0
0


1498
0
0
0
0
0
0


1499
60
0
60
0
0
0


1500
60
10
60
0
0
0


1501
50
20
60
0
0
0


1502
60
30
80
0
30
10


1503
10
10
20
0
0
0


1504
0
0
0
0
0
0


1505
0
10
0
0
0
0


1506
0
0
0
0
0
0


1507
0
0
0
0
0
0


1508
0
0
0
0
0
0


1509
0
0
0
0
0
0


1510
0
0
0
0
0
0


1511
0
0
0
0
0
0


1512
0
0
0
0
0
0


1513
0
0
0
0
0
0


1514
0
10
0
0
0
0


1515
0
0
0
0
0
0


1516
0
0
0
0
0
0


1517
50
10
60
30
0
10


1518
0
0
0
0
0
0


1519
0
10
0
0
0
0


1520
30
0
30
30
0
0


1522
0
10
0
0
0
0


1525
0
0
0
0
0
0


1526
0
10
20
10
0
0


1527
0
10
0
0
0
0


1528
0
0
0
0
0
0


1529
0
0
0
0
0
0


1530
0
0
0
0
0
0


1531
0
0
0
0
0
0


1532
0
0
0
0
0
0


1533
0
0
0
0
0
0


1534
0
0
0
0
0
0


1535
0
0
0
0
10
0


1536
0
0
0
0
0
0


1537
0
0
0
0
0
0


1538
0
0
30
0
0
0


1539
0
0
0
0
0
0


1540
0
10
0
10
0
0


1541
0
0
0
0
0
0


1542
0
0
0
0
0
0


1543
0
0
0
0
0
0


1544
0
10
0
0
0
0


1545
0
0
0
0
0
0


1546
70
20
80
20
60
0


1547
0
0
0
0
0
0


1548
0
0
0
0
0
0


1549
0
0
0
0
0
0


1550
0
10
0
0
30
0


1551
0
0
0
0
0
0


1552
0
10
0
0
0
0


1553
0
0
0
0
0
0


1554
0
0
0
0
0
0


1555
0
10
0
10
0
0


1556
0
0
0
0
0
0


1557
20
0
0
0
0
0


1558
10
0
0
0
0
0


1559
0
0
0
0
0
0


1560
0
0
0
0
0
0


1561
20
0
10
10
20
40


1562
0
10
0
0
10
0


1563
0
0
0
0
0
0


1564
0
0
0
0
0
0


1565
0
0
0
0
0
0


1566
10
0
0
0
0
0


1567
0
0
0
0
0
0


1568
10
0
0
0
0
0


1569
10
0
0
0
0
0


1570
0
0
0
0
0
0


1571
0
0
0
0
0
0


1572
0
0
0
10
0
0


1573
0
0
0
0
0
0


1574
0
0
0
0
0
0


1575
0
0
0
0
0
0


1576
60
20
40
20
0
0


1577
0
0
0
0
0
0


1578
20
0
10
10
20
10


1579
10
0
0
0
0
0


1580
0
0
0
0
0
0


1581
0
0
0
0
0
0


1582
0
0
0

0
0


1583
0
0
20
10
0
0


1584
0
10
40
20
0
0


1585
80
60
60
30
20
20


1586
0
0
0
0
0
10


1587
20
0
20
0
10
0


1588
80
80
70
20
0
0


1589
0
0
0
0
0
0


1590
0
0
70
20
0
0


1591
30
0
70
10
10
0


1592
10
0
60
40
0
10


1593
0
10
10
0
0
0


1594
20
0
20
0
0
0


1595
10
60
0
60
10
10


1596
30
0
60
10
10
0


1597
0
0
0
0
0
0


1598
80
40
80
60
50
20


1599
70
0
80
60
50
30


1600
0
0
0
0
0
0


1601
40
10
80
10
10
20


1602
20
0
60
50
50
20


1603
0
0
0
0
0
0


1604
0
0
0
0
0
0


1605
0
0
0
0
20
0


1606
40
0
70
0
40
0


1607
50
0
80
30
40
30


1608
10
10
10
30
10
0


1609
70
10
80
20
70
20


1610
0
0
0
0
0
0


1611
0
0
0
0
0
0


1612
0
0
0
0
0
0


1613
20
0
70
0
50
20


1614
0
0
0
0
0
0


1615
0
0
0
0
0
0


1616
10
0
20
10
50
0


1617
0
0
40
0
0
0


1618
0
0
0
0
0
0


1619
10
0
60
10
20
0


1620
0
0
0
0
0
0


1621
30
0
40
0
20
0


1622
0
0
0
0
0
0


1623
70
0
70
30
20
0


1624
20
10
80
20
30
10


1625
30
0
50
0
30
10


1626
0
0
0
0
0
0


1627
70
30
80
70
60
20


1628
70
0
80
20
50
20


1629
30
10
80
20
10
10


1630
0
0
0
0
0
0


1631
10
0
60
20
20
10


1632
0
0
0
0
0
0


1633
0
0
0
0
0
0


1634
0
0
0
0
0
0


1635
0
0
10
0
0
0


1636
50
0
70
0
0
0


1637
70
0
80
20
70
10


1638
0
0
0
0
0
0


1639
30
0
70
10
20
0


1640
0
0
0
0
0
0


1641
0
0
0
0
0
0


1642
0
0
30
0
0
0


1643
0
0
0
0
0
0


1644
0
0
20
10
0
0


1645
20
0
70
0
40
0


1646
0
0
10
0
0
0


1647
0
0
30
0
0
0


1648
0
0
0
0
0
0


1649
0
0
0
0
0
0


1650
80
50
80
10
70
20


1651
30
0
70
10
0
0


1652
20
0
20
0
0
0


1653
60
30
80
30
70
40


1654
20
0
40
20
20
20


1655
20
0
30
0
0
0


1656
10
0
30
0
20
0


1657
10
10
40
10
40
20


1658
0
0
0
0
10
0


1659
0
0
0
0
0
0


1660
0
0
0
0
0
0


1661
20
0
60
0
20
0


1662
0
0
0
0
0
0


1663
0
0
0
0
0
0


1664
60
40
80
20
80
10


1665
0
0
0
0
0
0


1667
0
0
0
0
0
0


1668
0
0
0
0
0
0


1669
30
0
50
20
0
0


1670
20
0
70
0
20
0


1671
70
70
80
70
30
10


1672
0
0
0
0
30
0


1673
0
0
0
0
0
0


1674
0
0
0
0
0
0


1675
0
0
0
0
0
0


1676
0
0
0
0
0
0


1677
10
0
30
0
0
0


1678
10
0
10
0
10
0


1679
80
0
80
50
30
20


1680
20
0
80
10
60
10


1682
0
0
0
0
0
0


1683
70
40
80
30
10
20


1684
0
0
0
0
0
0


1685
60
40
70
30
50
30


1686
70
10
70
20
20
20


1687
50
40
80
60
40
40


1688
70
30
80
20
0
0


1690
80
70
80
70
20
20


1691
70
0
80
60
0
10


1692
70
50
80
30
40
20


1693
30
10
60
50
50
30


1694
0
0
0
0
0
0


1695
80
70
80
20
10
10


1696
70
70
80
60
50
0


1697
70
80
80
60
60
30


1698
80
70
80
70
30
10


1699
80
30
80
30
0
0


1700
50
30
60
20
0
0


1701
60
30
60
0
0
0


1702
70
20
80
60
10
20


1703
70
0
70
60
60
40


1704
70
20
80
20
10
0


1705
30
0
70
20
0
0


1706
60
0
80
0
10
20


1707
70
70
80
40
0
20


1708
50
30
60
20
0
0


1709
70
60
80
50
10
10


1710








1711
70
10
80
30
0
0


1712
80
70
80
30
20
10


1713
80
50
80
60
0
0


1714
70
30
80
20
80
30


1716
60
10
70
0
0
0


1717
60
0
70
0
0
0


1718
70
50
80
60
40
40


1719
60
0
80
10
0
0


1720








1721
30
10
50
40
0
0


1722
60
0
70
30
10
10


1723
80
60
80
70
20
10


1724
70
30
70
30
10
10


1725
30
0
70
70
10
0


1726
30
30
70
10
0
0


1727
70
0
80
30
0
0


1728
80
60
80
20
0
30


1729
0
0
0
0
0
0


1730
40
0
20
0
0
0


1731
0
0
0
0
0
0


1732
0
0
10
0
10
10


1733
0
50
80
60
20
40


1734
0
0
0
0
0
0


1735
0
0
0
0
0
0


1736
30
0
80
0
0
0


1737
0
0
0
0
0
0


1738
40
0
40
0
10
10


1739
0
0
0
0
0
0


1740
0
0
40
0
0
0


1741
0
0
80
30
0
0


1742
70
0
80
0
20
10


1743
0
0
70
0
0
0


1744
10
0
20
0
10
0


1745
70
0
60
30
0
0


1746
0
0
10
10
20
0


1747
60
0
60
20
20
0


1748
0
0
0
0
0
0


1749
0
0
0
0
0
0


1750
0
10
0
10
10
0


1751
0
0
0
0
0
0


1752
0
0
0
0
0
0


1753
70
60
60
50
20
20


1754
70
60
80
70
40
30


1755
70
80
80
70
20
30


1757
10
0
20
0
0
0


1760
0
0
0
0
0
0


1761
0
0
0
40
0
0


1762
50
30
70
60
0
0


1763
60
20
60
40
0
10


1764
50
10
80
30
10
40


1765
30
10
60
0
0
0


1766
30
20
50
20
0
0


1767
50
10
70
30
0
0


1768
0
0
0
0
0
0


1769
0
0
10
0
0
0


1770
0
0
20
10
20
10


1771
0
0
0
0
0
0


1772
0
0
60
30
0
0


1773
80
80
80
10
20
20


1783
80
80
80
60
0
20


1784
0
0
0
0
0
0


1785
0
0
0
0
0
0


1786
0
0
10
0
0
0


1787
60
50
70
70
20
20


1788
0
10
0
0
10
10


1789
0
0
0
0
0
0


1790
70
70
80
20
0
20


1791
80
70
80
70
0
30


1792
70
40
80
30
0
20


1793
70
30
80
10
0
10


1794
40
50
60
50
40
0


1795
70
40
80
20
20
0


1796
0
0
0
10
10
0


1797
70
60
80
40
70
80


1798
0
0
20
0
0
0


1799
60
60
70
60
60
20


1800
10
0
20
10
10
0


1801
60
70
80
10
0
0


1802
60
0
70
0
0
40


1803
0
0
70
10
0
0


1804
50
0
70
50
0
10


1805
0
0
30
30
60
20


1806
20
0
60
0
0
0


1807
0
0
0
0
0
0


1808
20
0
30
0
0
0


1809
80
80
80
70
20
0


1810
60
0
80
60
10
30


1811
80
60
80
20
60
30


1812
0
0
80
50
20
10


1813
0
0
0
10
0
0


1814
0
0
0
0
0
0


1815
0
0
0
0
0
0


1816
80
80
80
60
40
30


1817
0
0
0
0
0
0


1818
30
30
80
10
0
0


1819
20
0
40
0
0
0


1820
0
0
0
0
0
0


1821
0
10
10
0
30
10


1822
80
40
80
10
10
30


1823
0
0
0
0
0
0


1824
0
0
0
0
0
0


1825
0
0
0
0
0
0


1826
10
20
40
20
0
0


1827
70
10
80
10
0
0


1828
80
10
80
60
0
20


1829
60
0
80
20
20
0


1833
0
0
0
0
0
0


1836
70
10
70
20
60
20







Post-Emergence (15.625 g ai/ha)













1396
80
70
80
40
70
40


1397
80
80
80
60
0
0


1398
80
30
80
0
0
0


1399
40
0
60
10
0
0


1400
50
10
60
0
20
10


1401
0
0
0
0
0
0


1402
80
70
80
10
10
0


1403
0
10
0
0
10
0


1404
10
20
0
0
20
10


1405
0
0
0
0
0
0


1406
0
20
0
0
0
0


1407
10
0
0
0
20
10


1408
0
0
0
0
0
0


1409
0
0
0
0
0
0


1410
0
0
0
0
0
0


1411
0
0
0
0
0
0


1412
0
20
0
0
30
0


1413
20
0
40
0
0
0


1414
50
20
70
0
10
0


1415
20
20
20
10
10
10


1416
0
0
0
0
0
0


1417
10
0
0
0
20
10


1418
20
10
0
0
0
0


1419
30
10
10
0
10
10


1420
10
10
50
0
0
0


1421
0
10
20
10
0
10


1422
0
10
0
0
0
0


1423
0
10
0
0
0
0


1424
0
0
0
0
10
0


1425
0
10
10
0
20
0


1426
0
10
0
0
0
0


1427
0
0
0
0
0
0


1428
20
10
30
10
10
0


1429
0
10
0
0
0
0


1430
0
0
0
0
0
0


1431
0
0
0
0
0
0


1432
0
0
0
0
0
0


1433
0
0
0
0
0
0


1434
0
10
0
0
0
0


1435
0
0
0
0
0
0


1436
0
0
0
0
0
0


1437
0
0
0
0
0
0


1438
0
0
0
0
0
0


1439
0
10
0
0
0
0


1440
0
0
0
0
0
0


1441
0
0
0
0
0
0


1442
0
0
0
0
0
0


1443
0
0
0
0
0
0


1444
0
10
0
0
10
0


1445
0
0
0
0
0
0


1446
0
0
0
0
0
0


1447
0
0
10
0
0
0


1448
0
0
0
0
0
0


1449
0
0
0
0
0
0


1450
0
0
0
0
0
0


1451
0
0
0
0
0
0


1452
0
0
0
0
0
0


1453
0
10
10
0
0
0


1454
0
10
30
10
0
0


1455
0
10
10
0
0
0


1456
10
10
50
30
0
0


1457
0
0
0
0
0
0


1458
10
10
30
10
10
0


1459
0
10
10
0
30
0


1460
20
10
40
0
0
0


1461
0
10
20
0
0
0


1462
0
0
0
0
0
0


1463
0
0
0
0
0
0


1464
20
20
70
10
10
10


1465
0
10
0
0
10
10


1466
0
0
0
0
10
0


1468
10
10
30
10
10
0


1471
30
10
10
10
10
10


1472
10
10
10
20
0
0


1473
40
20
60
0
0
0


1474
20
10
60
40
30
10


1475
30
30
70
20
10
10


1476
40
10
60
20
10
10


1477
50
30
50
0
0
0


1478
10
0
10
0
0
0


1479
0
10
0
0
0
0


1480
50
20
60
0
0
0


1481
30
20
40
0
0
0


1482
30
20
30
0
0
0


1483
30
20
30
0
40
10


1484
20
20
10
0
10
0


1485
50
40
60
0
0
0


1486
40
10
60
0
0
0


1487
50
20
60
0
20
0


1488
0
0
0
0
0
0


1489
0
10
0
0
0
0


1490
50
0
50
0
0
0


1491
0
0
0
0
0
0


1492
0
0
0
0
0
0


1493
40
10
40
0
0
0


1494
30
10
60
10
0
0


1496
20
10
20
0
0
0


1497
20
10
30
0
0
0


1498
0
0
0
0
0
0


1499
50
10
60
20
0
0


1500
10
10
40
0
0
0


1501
10
10
40
0
0
0


1502
20
0
60
0
20
0


1503
0
0
0
0
0
0


1504
0
0
0
0
0
0


1505
0
0
0
0
0
0


1506
0
0
0
0
0
0


1507
0
0
0
0
0
0


1508
0
0
0
0
0
0


1509
0
0
0
0
0
0


1510
0
0
0
0
0
0


1511
0
0
0
0
0
0


1512
0
0
0
0
0
0


1513
0
0
0
0
0
0


1514
0
0
0
0
0
0


1515
0
0
0
0
0
0


1516
0
0
0
0
0
0


1517
0
0
20
20
0
0


1518
0
0
0
0
0
0


1519
0
10
0
0
0
0


1520
0
0
0
10
0
0


1522
0
0
0
0
0
0


1525
0
0
0
0
0
0


1526
0
0
0
0
0
0


1527
0
10
0
0
0
0


1528
0
0
0
0
0
0


1529
0
0
0
0
0
0


1530
0
0
0
0
0
0


1531
0
0
0
0
0
0


1532
0
0
0
0
0
0


1533
0
0
0
0
0
0


1534
0
0
0
0
0
0


1535
0
0
0
0
0
0


1536
0
0
0
0
0
0


1537
0
0
0
0
0
0


1538
0
0
10
0
0
0


1539
0
0
0
0
0
0


1540
0
0
0
0
0
0


1541
0
0
0
0
0
0


1542
0
0
0
0
0
0


1543
0
0
0
0
0
0


1544
0
10
0
0
0
0


1545
0
0
0
0
0
0


1546
40
0
60
0
30
0


1547
0
0
0
0
0
0


1548
0
0
0
0
0
0


1549
0
0
0
0
0
0


1550
0
0
0
0
0
0


1551
0
0
0
0
0
0


1552
0
10
0
0
0
0


1553
0
0
0
0
0
0


1554
0
0
0
0
0
0


1555
0
0
0
0
0
0


1556
0
0
0
0
0
0


1557
0
0
0
0
0
0


1558
0
0
0
0
0
0


1559
0
0
0
0
0
0


1560
0
0
0
0
0
0


1561
0
0
0
0
0
0


1562
0
0
0
0
0
0


1563
0
0
0
0
0
0


1564
0
0
0
0
0
0


1565
0
0
0
0
0
0


1566
0
0
0
0
0
0


1567
0
0
0
0
0
0


1568
0
0
0
0
0
0


1569
0
0
0
0
0
0


1570
0
0
0
0
0
0


1571
0
0
0
0
0
0


1572
0
0
0
0
0
0


1573
0
0
0
0
0
0


1574
0
0
0
0
0
0


1575
0
0
0
0
0
0


1576
10
0
30
0
0
0


1577
0
0
0
0
0
0


1578
0
0
0
0
0
20


1579
0
0
0
0
0
0


1580
0
0
0
0
0
0


1581
0
0
0
0
0
0


1582
0
0
0
0
0
0


1583
0
0
0
0
0
0


1584
0
0
0
0
0
0


1585
70
30
60
20
0
0


1586
0
0
0
0
0
0


1587
0
0
0
0
0
0


1588
80
60
60
70
0
0


1589
0
0
0
0
0
0


1590
0
0
0
0
0
0


1591
0
0
0
0
0
0


1592
0
0
0
0
0
0


1593
0
0
0
0
0
0


1594
0
0
0
0
0
0


1595
10
0
0
0
0
0


1596
0
0
0
0
0
0


1597
0
0
0
0
0
0


1598
30
0
80
30
30
0


1599
10
0
60
50
0
0


1600
0
0
0
0
0
0


1601
0
0
0
0
0
0


1602
0
0
0
10
0
0


1603
0
0
0
0
0
0


1604
0
0
0
0
0
0


1605
0
0
0
0
0
0


1606
20
0
40
0
40
0


1607
0
0
50
20
0
10


1608
0
0
0
40
0
0


1609
20
10
70
20
30
0


1610
0
0
0
0
0
0


1611
0
0
0
0
0
0


1612
0
0
0
0
0
0


1613
0
0
20
0
0
0


1614
0
0
0
0
0
0


1615
0
0
0
0
0
0


1616
10
0
40
0
20
10


1617
0
0
20
0
0
0


1618
0
0
0
0
0
0


1619
0
0
0
0
0
0


1620
0
0
0
0
0
0


1621
10
0
10
0
0
0


1622
0
0
0
0
0
0


1623
10
0
30
30
10
0


1624
0
0
10
10
0
0


1625
0
0
0
0
0
0


1626
0
0
0
0
0
0


1627
20
0
70
60
20
0


1628
30
0
70
20
10
30


1629
0
0
0
20
10
20


1630
0
0
0
0
0
0


1631
0
0
0
0
0
0


1632
0
0
0
0
0
0


1633
0
0
0
0
0
0


1634
0
0
0
0
0
0


1635
0
0
0
0
0
0


1636
10
0
50
0
0
0


1637
20
0
60
0
40
0


1638
0
0
0
0
0
0


1639
10
0
30
0
0
0


1640
0
0
0
0
0
0


1641
0
0
0
0
0
0


1642
0
0
0
0
0
0


1643
0
0
0
0
0
0


1644
0
0
0
0
0
0


1645
0
0
0
0
0
0


1646
0
0
0
0
0
0


1647
0
0
0
0
0
0


1648
0
0
0
0
0
0


1649
0
0
0
0
0
0


1650
40
10
70
20
10
0


1651
0
0
0
0
0
0


1652
0
0
0
0
0
0


1653
30
0
60
10
0
0


1654
0
0
20
10
10
0


1655
0
0
0
0
0
0


1656
10
0
20
0
0
0


1657
0
0
0
0
0
0


1658
0
0
0
0
0
0


1659
0
0
0
0
0
0


1660
0
0
0
0
0
0


1661
0
0
0
0
0
0


1662
0
0
0
0
0
0


1663
0
0
0
0
0
0


1664
0
0
60
0
20
0


1665
0
0
0
0
0
0


1667
0
0
0
0
0
0


1668
0
0
0
0
0
0


1669
0
10
30
0
0
0


1670
0
0
0
0
0
0


1671
70
60
70
0
10
0


1672
0
0
0
0
0
0


1673
0
0
0
0
0
0


1674
0
0
0
0
0
0


1675
0
0
0
0
0
0


1676
0
0
0
0
0
0


1677
0
0
10
0
0
0


1678
0
0
0
0
10
0


1679
40
0
80
0
0
0


1680
20
0
30
10
50
0


1682
0
0
0
0
0
0


1683
70
20
70
30
30
0


1684
0
0
0
0
0
0


1685
30
10
70
40
40
10


1686
30
0
60
20
30
30


1687
0
10
60
20
40
40


1688
30
0
60
0
0
0


1690
70
10
80
20
0
0


1691
30
0
60
0
0
0


1692
40
20
60
40
0
0


1693
0
0
0
0
20
0


1694
0
0
0
0
0
0


1695
80
30
80
10
10
0


1696
40
50
70
20
70
0


1697
60
10
80
30
20
0


1698
60
20
80
10
20
0


1699
60
0
80
10
0
0


1700
20
30
40
20
0
0


1701
10
10
40
0
0
0


1702
60
20
70
10
10
10


1703
50
0
70
60
20
10


1704
40
0
70
30
0
0


1705
20
10
70
0
0
0


1706
40
0
70
20
0
0


1707
70
60
80
40
0
0


1708
40
10
40
20
0
0


1709
30
30
70
10
20
20


1710








1711
30
0
70
10
0
0


1712
50
40
80
10
0
10


1713
10
0
60
20
0
0


1714
40
20
70
10
70
0


1716
0
0
40
0
0
0


1717
0
0
30
0
0
0


1718
50
30
70
10
30
20


1719
0
0
60
0
0
0


1720








1721
0
0
0
0
0
0


1722
10
10
60
20
0
0


1723
30
30
70
30
20
10


1724
40
0
70
40
0
0


1725
0
10
0
30
0
0


1726
0
10
0
10
20
0


1727
20
0
30
0
0
0


1728
70
60
80
0
20
30


1729
0
0
0
0
0
0


1730
0
0
0
0
0
0


1731
0
0
0
0
0
0


1732
0
0
0
0
0
0


1733
0
0
10
20
10
0


1734
0
0
0
0
0
0


1735
0
0
0
0
0
0


1736
0
0
30
0
0
0


1737
0
0
0
0
0
0


1738
0
0
20
0
20
0


1739
0
0
0
0
0
0


1740
0
0
0
0
0
0


1741
0
0
50
0
0
0


1742
0
0
70
0
0
0


1743
0
0
20
0
0
0


1744
0
0
0
0
0
0


1745
10
0
10
0
0
0


1746
0
0
0
0
0
0


1747
0
0
10
0
10
0


1748
0
0
0
0
0
0


1749
0
0
0
0
0
0


1750
0
0
0
0
0
0


1751
0
0
0
0
0
0


1752
0
0
0
0
0
0


1753
40
60
60
20
0
10


1754
30
10
60
30
0
10


1755
60
10
70
60
10
10


1757
0
0
0
0
0
0


1760
0
0
0
0
0
0


1761
0
0
0
0
0
0


1762
10
20
60
30
20
10


1763
40
20
60
30
0
0


1764
40
10
70
10
0
20


1765
0
0
10
0
0
0


1766
60
30
20
0
0
0


1767
40
10
70
30
0
0


1768
0
0
0
0
0
0


1769
0
0
0
0
0
0


1770
0
0
0
0
0
0


1771
0
0
0
0
0
0


1772
0
0
10
0
0
0


1773
80
70
80
20
20
0


1783
70
70
80
10
0
0


1784
0
0
0
0
0
0


1785
0
0
0
0
0
0


1786
0
0
0
0
0
0


1787
20
30
40
50
20
20


1788
0
0
0
0
0
0


1789
0
0
0
0
0
0


1790
50
50
70
20
0
0


1791
70
30
80
20
0
10


1792
30
20
70
10
0
0


1793
30
10
70
0
0
0


1794
0
20
0
20
0
0


1795
20
0
60
10
0
0


1796
0
0
0
0
0
0


1797
30
10
50
0
30
60


1798
0
0
0
0
0
0


1799
0
10
20
10
0
0


1800
0
0
0
0
0
0


1801
20
10
70
0
0
0


1802
0
0
40
0
0
0


1803
0
0
20
0
0
0


1804
0
0
0
0
0
0


1805
0
0
0
0
10
0


1806
0
0
0
0
0
0


1807
0
0
0
0
0
0


1808
0
0
0
0
0
0


1809
80
80
80
20
20
0


1810
0
0
20
20
0
20


1811
80
40
80
40
20
10


1812
0
0
0
0
0
0


1813
0
0
0
0
0
0


1814
0
0
0
0
0
0


1815
0
0
0
0
0
0


1816
80
70
80
10
10
0


1817
0
0
0
0
0
0


1818
0
0
40
0
0
0


1819
0
0
0
0
0
0


1820
0
0
0
0
0
0


1821
0
10
0
0
0
0


1822
70
0
70
20
0
0


1823
0
0
0
0
0
0


1824
0
0
0
0
0
0


1825
0
0
0
0
0
0


1826
0
0
0
0
0
0


1827
0
0
50
0
0
0


1828
30
0
70
20
0
0


1829
0
20
70
20
0
0


1833
0
0
0
0
0
0


1836
0
0
50
20
20
10








Claims
  • 1. A compound of from Formula 1, an N-oxide of the compound, or a salt of the compound or N-oxide:
  • 2. A herbicidal composition comprising: a compound N-oxide or salt of claim 1; anda surfactant, solid diluent or liquid diluent.
  • 3. The herbicidal composition of claim 2, wherein the composition further comprises an additional active ingredient selected from the group consisting of other herbicides and herbicide safeners.
  • 4. A herbicidal mixture comprising: a compound, N-oxide or salt of claim 1, andan additional active ingredient selected from (b1) through (b16) and salts of compounds of (hi) through (b16).
  • 5. A herbicidal mixture comprising: a compound, N-oxide or salt of claim 1; andan additional active ingredient selected from (b2), (b9) and (b12); and salts of compounds of (hi), (b9) and (b12).
  • 6. A method for controlling the growth of undesired vegetation comprising contacting the vegetation or its environment with a herbicidally effective amount of a compound, N-oxide or salt of claim 1.
  • 7. A compound of the following formula
CROSS-REFERENCE TO RELATED PATENT APPLICATION

This disclosure claims priority to U.S. Provisional Patent Application No. 62/170,129 (filed Jun. 2, 2015). The entire text of the above-referenced patent application is incorporated by reference into this patent filing

US Referenced Citations (38)
Number Name Date Kind
3741989 Zaugg Jun 1973 A
3959481 Davis et al. May 1976 A
4594094 Kollmeyer Jun 1986 A
4874422 Woolard Oct 1989 A
5196434 Whitehead et al. Mar 1993 A
5856273 Kay et al. Jan 1999 A
7205318 Qiao et al. Apr 2007 B2
7355053 Reinhard et al. Apr 2008 B2
7375232 Clark et al. May 2008 B2
8293926 Yasuoka et al. Oct 2012 B2
8461202 Sancho Sanz et al. Jun 2013 B2
8575154 Kori et al. Nov 2013 B2
8946216 Deng et al. Feb 2015 B2
9119397 Yerkes Sep 2015 B2
9446995 Chong Sep 2016 B2
9737073 Gifford Aug 2017 B2
9944602 Satterfield et al. Apr 2018 B2
9969728 Defays et al. May 2018 B2
10294202 Satterfield May 2019 B2
10875838 Chen et al. Dec 2020 B2
20040242671 Grimee et al. Dec 2004 A1
20070123508 Olsson et al. May 2007 A1
20090203694 Hurley et al. Aug 2009 A1
20110218199 Georges et al. Sep 2011 A1
20150173371 Mann et al. Jun 2015 A1
20160137639 Kotoku et al. May 2016 A1
20160297756 Satterfield et al. Oct 2016 A1
20180049437 Satterfield et al. Feb 2018 A1
20180057442 Satterfield Mar 2018 A1
20180077931 Stevenson et al. Mar 2018 A1
20180141904 Campbell et al. May 2018 A1
20180213788 Satterfield et al. Aug 2018 A1
20180215760 Campbell et al. Aug 2018 A1
20200009520 Puri Jan 2020 A1
20200095202 Puri Mar 2020 A1
20200115337 Campbell et al. Apr 2020 A1
20200120931 Campbell Apr 2020 A1
20200154709 McMahon May 2020 A1
Foreign Referenced Citations (29)
Number Date Country
102531918 Oct 2013 CN
1262277 Mar 1968 DE
2336104 Jun 2011 EP
1462DEL08 Jun 2008 IN
53-056288 May 1978 JP
54-088114 Jul 1979 JP
08-269145 Oct 1996 JP
20130142477 Dec 2013 KR
2555370 Jul 2015 RU
200009481 Feb 2000 WO
2003024222 Mar 2003 WO
2004046081 Jun 2004 WO
2006081562 Aug 2006 WO
2009062371 May 2009 WO
2012034957 Mar 2012 WO
2015084796 Jun 2015 WO
2016003997 Jan 2016 WO
2016094117 Jun 2016 WO
2016164201 Oct 2016 WO
2016176082 Nov 2016 WO
2016182780 Nov 2016 WO
2016196019 Dec 2016 WO
2017023515 Feb 2017 WO
2017075559 May 2017 WO
2018118384 Jun 2018 WO
20180175226 Sep 2018 WO
20180175231 Sep 2018 WO
2018222646 Dec 2018 WO
2018222647 Dec 2018 WO
Non-Patent Literature Citations (15)
Entry
Campaigne et el.; Synthesis of Some Ureidodihydrofurans and Related Pyrimidones as Potential Antimalarials; J. Med. Chem.; 1969; 339-342. (XP002278920).
Cauliez et al.; “Studies on Pyrrolidinones. On the Carbamoylation of Some Pyroglutamic Derivatives”; J. Het. Chem.; 33; 1996; 1233-1237. (XP055297107).
Hwang et al.; “Diastereoselective Synthesis of Oxazolidinone Derivatives and Their Antifungal Activities”; Korean J. of Med. Chem.; vol. 4, No. 1; 1994; 52-56. (XP009191451).
IPCOM000241978D; Jun. 11, 2015.
Murata et al.; “Oxidation of N-Acyl-Pyrrolidines and -Piperidines with Iron(II)-Hydrogen Peroxide and an Iron Complex-Molecular Oxygen”; J. Chem. Soc. Perkin Trans.; 1987; 1259-1262. (XP055297105).
PubChem Entry CID 29937915 (4S)-4[3-(trifluoromethyl)phenyl]pyrrolidin-2-one: May 28, 2009.
XP002734980; Jan. 20, 2002.
XP002734981; WO0009481; Feb. 24, 2000.
XP002759805; Jan. 20, 2002.
XP002759806; Mar. 23, 2009.
Hajra, S. et al., “Organocatalytic Enantioselective Conjugate Addition of Nitromethane to Alkylidinemalonates: Asymetric Synthesis of Pyrrolidine-3-Carboxylic Acid Derivatives”, RSC Advances 2013, 3, 10185-10188.
Banerjee et al., “A Stereoselective Cyclization Strategy for the Preparation of gamma-Lactams and Their Use in the Synthesis of alpha-Methyl-beta-Proline”, J. Org. Chem. 2012, vol. 77, pp. 10925-10930.
Wang et al. “Asymetric Cyanation of Activated Olefins with Ethyl Cyanoformate Catalyzed by a Modular Titanium Catalyst”, Org. Lett. 2010, vol. 12(6), pp. 1280-1283.
V. G. Belikov, Pharmaceutical Chemistry, Chapter 2.6, “The relationship between chemical structure, properties of substances and their effect on the body”, M.: MEDpress-inform, 2007, p. 27-29.
Dyson, G et al., “Chemistry of Synthetic Medicinal Substances”, Chemistry of Synthetic Drugs, 1964, pp. 12-19.
Related Publications (1)
Number Date Country
20200347017 A1 Nov 2020 US
Provisional Applications (1)
Number Date Country
62170129 Jun 2015 US
Continuations (1)
Number Date Country
Parent 15573598 US
Child 16875369 US