TREA

Intermediates to prepare herbicidal pyrimidone derivatives

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Information

  • Patent Grant
  • 9630928
  • Patent Number
    9,630,928
  • Date Filed
    Wednesday, September 30, 2015
    8 years ago
  • Date Issued
    Tuesday, April 25, 2017
    7 years ago
Information
Abstract
Disclosed are compounds of Formula 1, including all stereoisomers, N-oxides, and salts thereof,
Description
FIELD OF THE INVENTION

This invention relates to certain bis-nitrogen heterocycles, their salts and compositions, and methods of their use for controlling undesirable vegetation. This invention also relates to certain intermediates and a method useful for preparing these bis-nitrogen heterocycles and their salts. This invention also relates to certain bis-nitrogen oxo or sulfono heterocycles, their salts and compositions, and methods of their use for controlling undesirable vegetation.


BACKGROUND OF THE INVENTION

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.


International patent application publication WO 2007/088876 discloses pyridone compounds of Formula i




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wherein inter alia R1 is C1-C6 alkyl; R2 and R3 are each independently hydrogen, cyano, or nitro; and A is a A-1 through A-5 as defined therein as herbicides.


The bis-nitrogen containing oxo and sulfono heterocycles of the present invention are not disclosed in this publication.


SUMMARY OF THE INVENTION

This invention is directed to compounds of Formula 1 (including all stereoisomers), N-oxides, and salts thereof, agricultural compositions containing them and their use as herbicides:




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wherein

    • X is CH;
    • Y is C(O);
    • A is a radical selected from the group consisting of




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    • B1 and B3 are each independently a radical selected from the group consisting of







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    • B2 is a radical selected from the group consisting of







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    • R1 is phenyl, phenylsulfonyl, —W1(phenyl), —W1(S-phenyl), —W1(SO2-phenyl), —W2(SO2CH2-phenyl) or —W2(SCH2-phenyl), each optionally substituted on ring members with up to five substituents selected from R21; or -G or —W2G; or cyano, hydroxy, amino, —C(═O)OH, —C(═O)NHCN, —C(═O)NHOH, —SO2NH2, —SO2NHCN, —SO2NHOH, —NHCHO, C1-C10 alkyl, C2-C10 alkenyl, C2-C10 alkynyl, C1-C10 haloalkyl, C2-C10 haloalkenyl, C2-C12 haloalkynyl, C3-C12 cycloalkyl, C3-C12 halocycloalkyl, C4-C14 alkylcycloalkyl, C4-C14 cycloalkylalkyl, C6-C18 cycloalkylcycloalkyl, C4-C14 halocycloalkylalkyl, C5-C16 alkylcycloalkylalkyl, C3-C12 cycloalkenyl, C3-C12 halocycloalkenyl, C2-C12 alkoxyalkyl, C3-C12 alkoxyalkenyl, C4-C14 alkylcycloalkyl, C4-C14 alkoxycycloalkyl, C4-C14 cycloalkoxyalkyl, C5-C14 cycloalkoxyalkoxyalkyl, C3-C14 alkoxyalkoxyalkyl, C2-C12 alkylthioalkyl, C2-C12 alkylsulfinylalkyl, C2-C12 alkylsulfonylalkyl, C2-C12 alkylaminoalkyl, C3-C14 dialkylaminoalkyl, C2-C12 haloalkylaminoalkyl, C4-C14 cycloalkylaminoalkyl, C2-C12 alkylcarbonyl, C2-C12 haloalkylcarbonyl, C4-C14 cycloalkylcarbonyl, C2-C12 alkoxycarbonyl, C4-C16 cycloalkoxycarbonyl, C5-C14 cycloalkylalkoxycarbonyl, C2-C12 alkylaminocarbonyl, C3-C14 dialkylaminocarbonyl, C4-C14 cycloalkylaminocarbonyl, C2-C9 cyanoalkyl, C1-C10 hydroxyalkyl, C4-C14 cycloalkenylalkyl, C2-C12 haloalkoxyalkyl, C2-C12 alkoxyhaloalkyl, C2-C12 haloalkoxyhaloalkyl, C4-C14 halocycloalkoxyalkyl, C4-C14 cycloalkenyloxyalkyl, C4-C14 halocycloalkenyloxyalkyl, C3-C14 dialkoxyalkyl, C3-C14 alkoxyalkylcarbonyl, C3-C14 alkoxycarbonylalkyl, C2-C12 haloalkoxycarbonyl, C1-C10 alkoxy, C1-C10 haloalkoxy, C3-C12 cycloalkoxy, C3-C12 halocycloalkoxy, C4-C14 cycloalkylalkoxy, C2-C10 alkenyloxy, C2-C10 haloalkenyloxy, C2-C10 alkynyloxy, C3-C10 haloalkynyloxy, C2-C12 alkoxyalkoxy, C2-C12 alkylcarbonyloxy, C2-C12 haloalkylcarbonyloxy, C4-C14 cycloalkylcarbonyloxy, C3-C14 alkylcarbonylalkoxy, C1-C10 alkylthio, C1-C10 haloalkylthio, C3-C12 cycloalkylthio, C1-C10 alkylsulfinyl, C1-C10 haloalkylsulfinyl, C1-C10 alkylsulfonyl, C1-C10 haloalkylsulfonyl, C3-C12 cycloalkylsulfonyl, C2-C12 alkylcarbonylthio, C2-C12 alkyl(thiocarbonyl)thio, C3-C12 cycloalkylsulfinyl, C1-C10 alkylaminosulfonyl, C2-C12 dialkylaminosulfonyl, C1-C10 alkylamino, C2-C12 dialkylamino, C1-C10 haloalkylamino, C2-C12 halodialkylamino, C3-C12 cycloalkylamino, C2-C12 alkylcarbonylamino, C2-C12 haloalkylcarbonylamino, C1-C10 alkylsulfonylamino, C1-C10 haloalkylsulfonylamino or C4-C14 cycloalkyl(alkyl)amino;

    • W1 is C1-C6 alkylene, C2-C6 alkenylene or C2-C6 alkynylene;

    • W2 is C1-C6 alkylene;

    • R2 is phenyl or —W3(phenyl), each optionally substituted on ring members with up to five substituents selected from R21; or -G or —W4G; or H, cyano, hydroxy, amino, nitro, —CHO, —C(═O)OH, —C(═O)NH2, —C(═S)NH2, —C(═O)NHCN, —C(═O)NHOH, —SH, —SO2NH2, —SO2NHCN, —SO2NHOH, —SF5, —NHCHO, —NHNH2, —NHOH, —NHCN, —NHC(═O)NH2, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C4-C10 alkylcycloalkyl, C4-C10 cycloalkylalkyl, C6-C14 cycloalkylcycloalkyl, C4-C10 halocycloalkylalkyl, C5-C12 alkylcycloalkylalkyl, C3-C8 cycloalkenyl, C3-C8 halocycloalkenyl, C2-C8 alkoxyalkyl, C3-C10 alkoxyalkenyl, C4-C10 cycloalkoxyalkyl, C3-C10 alkoxyalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylaminoalkyl, C3-C10 dialkylaminoalkyl, C2-C8 haloalkylaminoalkyl, C4-C10 cycloalkylaminoalkyl, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C10 cycloalkylcarbonyl, C2-C8 alkoxycarbonyl, C4-C10 cycloalkoxycarbonyl, C5-C12 cycloalkylalkoxycarbonyl, C2-C8 alkylaminocarbonyl, C3-C10 dialkylaminocarbonyl, C4-C10 cycloalkylaminocarbonyl, C2-C5 cyanoalkyl, C1-C6 hydroxyalkyl, C4-C10 cycloalkenylalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkoxyhaloalkyl, C2-C8 haloalkoxyhaloalkyl, C4-C10 halocycloalkoxyalkyl, C4-C10 cycloalkenyloxyalkyl, C4-C10 halocycloalkenyloxyalkyl, C3-C10 dialkoxyalkyl, C3-C10 alkoxyalkylcarbonyl, C3-C10 alkoxycarbonylalkyl, C2-C8 haloalkoxycarbonyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C8 cycloalkoxy, C3-C8 halocycloalkoxy, C4-C10 cycloalkylalkoxy, C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, C2-C6 alkynyloxy, C3-C6 haloalkynyloxy, C2-C8 alkoxyalkoxy, C2-C8 alkylcarbonyloxy, C2-C8 haloalkylcarbonyloxy, C4-C10 cycloalkylcarbonyloxy, C3-C10 alkylcarbonylalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3-C8 cycloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C3-C8 trialkylsilyl, C3-C8 cycloalkenyloxy, C3-C8 halocycloalkenyloxy, C2-C8 haloalkoxyalkoxy, C2-C8 alkoxyhaloalkoxy, C2-C8 haloalkoxyhaloalkoxy, C3-C10 alkoxycarbonylalkoxy, C2-C8 alkyl(thiocarbonyl)oxy, C2-C8 alkylcarbonylthio, C2-C8 alkyl(thiocarbonyl)thio, C3-C8 cycloalkylsulfinyl, C1-C6 alkylaminosulfonyl, C2-C8 dialkylaminosulfonyl, C3-C10 halotrialkylsilyl, C1-C6 alkylamino, C2-C8 dialkylamino, C1-C6 haloalkylamino, C2-C8 halodialkylamino, C3-C8 cycloalkylamino, C2-C8 alkylcarbonylamino, C2-C8 haloalkylcarbonylamino, C1-C6 alkylsulfonylamino, C1-C6 haloalkylsulfonylamino or C4-C10 cycloalkyl(alkyl)amino; or

    • R1 and R2 are taken together along with the atoms to which they are attached to make a 5-, 6- or 7-membered unsaturated, partially unsaturated or fully unsaturated ring along with members consisting of up to 2 oxygen atoms, 2 nitrogen atoms or 2 sulfur atoms or up to two —S(O)—, —S(O)2—, —C(O)— groups optionally substituted on carbon atom ring members selected from halogen, cyano, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C3-C8 cycloalkyl and C2-C8 alkoxyalkyl; and phenyl optionally substituted with up to 5 substituents selected from cyano, nitro, halogen, C1-C6 alkyl, C1-C6 alkoxy and C1-C6 haloalkoxy; and optionally substituted on nitrogen ring members selected from H and C1-C6 alkyl; and phenyl optionally substituted with up to 5 substituents selected from cyano, nitro, halogen, C1-C6 alkyl, C1-C6 alkoxy and C1-C6 haloalkoxy;

    • W3 is C1-C6 alkylene, C2-C6 alkenylene or C2-C6 alkynylene;

    • W4 is C1-C6 alkylene;

    • R3 is H, halogen, cyano, hydroxy, —O−M+, amino, nitro, —CHO, —C(═O)OH, —C(═O)NH2, —C(═S)NH2, —SH, —SO2NH2, —SO2NHCN, —SO2NHOH, —OCN, —SCN, —SF5, —NHNH2, —NHOH, —N═C═O, —N═C═S, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C8 cycloalkoxy, C3-C8 halocycloalkoxy, C4-C10 cycloalkylalkoxy, C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, C2-C6 alkynyloxy, C3-C6 haloalkynyloxy, C2-C8 alkoxyalkoxy, C2-C8 alkylcarbonyloxy, C2-C8 haloalkylcarbonyloxy, C4-C10 cycloalkylcarbonyloxy, C3-C10 alkylcarbonylalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3-C8 cycloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C1-C6 alkylsulfonyloxy, C1-C6 alkylamino, C2-C8 dialkylamino, C1-C6 haloalkylamino, C2-C8 halodialkylamino, C3-C8 cycloalkylamino, C2-C8 alkylcarbonylamino, C2-C8 haloalkylcarbonylamino, C1-C6 alkylsulfonylamino or C1-C6 haloalkylsulfonylamino; or benzyloxy, phenyloxy, benzylcarbonyloxy, phenylcarbonyloxy, phenylsulfonyloxy, benzylsulfonyloxy, phenylthio, benzylthio, phenylsulfinyl, benzylsulfinyl, phenylsulfonyl or benzylsulfonyl, each optionally substituted on ring members with up to five substituents selected from R21;

    • M+ is an alkali metal cation or an ammonium cation;

    • R4, R5, R6 and R7 are each independently H, halogen, hydroxy, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C8 cycloalkoxy or C3-C8 halocycloalkoxy; or phenyl or benzyl, each optionally substituted on ring members with up to five substituents selected from R21;

    • R8 is H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C8 cycloalkyl or C3-C8 halocycloalkyl; or benzyl optionally substituted on ring members with up to five substituents selected from R21;

    • R9 is H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C4-C10 alkylcycloalkyl, C4-C10 cycloalkylalkyl, C6-C14 cycloalkylcycloalkyl, C4-C10 halocycloalkylalkyl, C5-C12 alkylcycloalkylalkyl, C3-C8 cycloalkenyl, C3-C8 halocycloalkenyl, C2-C8 alkoxyalkyl, C4-C10 cycloalkoxyalkyl, C3-C10 alkoxyalkoxyalkyl or C2-C8 alkylthioalkyl;

    • R10 is H, halogen, cyano, hydroxy, amino, nitro, SH, —SO2NH2, —SO2NHCN, —SO2NHOH, —OCN, —SCN, —SF5, —NHCHO, —NHNH2, —N3, —NHOH, —NHCN, —NHC(═O)NH2, —N═C═O, —N═C═S, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C4-C10 alkylcycloalkyl, C4-C10 cycloalkylalkyl, C6-C14 cycloalkylcycloalkyl, C4-C10 halocycloalkylalkyl, C5-C12 alkylcycloalkylalkyl, C3-C8 cycloalkenyl, C3-C8 halocycloalkenyl, C2-C8 alkoxyalkyl, C4-C10 cycloalkoxyalkyl, C3-C10 alkoxyalkoxyalkyl or C2-C8 alkylthioalkyl;

    • R11 is H, halogen, cyano, hydroxy, amino, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C4-C10 alkylcycloalkyl, C4-C10 cycloalkylalkyl, C4-C10 halocycloalkylalkyl, C5-C12 alkylcycloalkylalkyl, C3-C8 cycloalkenyl, C3-C8 halocycloalkenyl, C2-C8 alkoxyalkyl, C4-C10 cycloalkoxyalkyl, C3-C10 alkoxyalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl or C2-C8 alkylsulfonylalkyl; or phenyl optionally substituted with up to five substituents selected from R21;

    • R12 is H, halogen, cyano, hydroxy, amino, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C4-C10 alkylcycloalkyl, C4-C10 cycloalkylalkyl, C6-C14 cycloalkylcycloalkyl, C4-C10 halocycloalkylalkyl, C5-C12 alkylcycloalkylalkyl, C3-C8 cycloalkenyl, C3-C8 halocycloalkenyl or C2-C8 alkoxycarbonylamino;

    • R13 is H, halogen, cyano, hydroxy, amino, nitro or C2-C8 alkoxycarbonyl;

    • n is 0, 1, or 2;

    • each R14, R15, R18 and R19 is independently H, halogen, cyano, hydroxy or C1-C6 alkyl; or

    • a pair of R14 and R18 is taken together as C2-C6 alkylene or C2-C6 alkenylene;

    • R20 is H, C1-C6 haloalkyl, C2-C6 haloalkenyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C8 cycloalkoxy, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl or C3-C8 cycloalkyl;

    • T is C1-C6 alkylene or C2-C6 alkenylene;

    • each G is independently a 5- or 6-membered heterocyclic ring or an 8-, 9- or 10-membered fused bicyclic ring system, each ring or ring system optionally substituted with up to five substituents selected from R21 on carbon ring members and R22 on nitrogen ring members;

    • each R21 is independently halogen, cyano, hydroxy, amino, nitro, —CHO, —C(═O)OH, —C(═O)NH2, —C(═S)NH2, —C(═O)NHCN, —C(═O)NHOH, —SH, —SO2NH2, —SO2NHCN, —SO2NHOH, —OCN, —SCN, —SF5, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C4-C10 alkylcycloalkyl, C4-C10 cycloalkylalkyl, C3-C8 cycloalkenyl, C3-C8 halocycloalkenyl, C2-C8 alkoxyalkyl, C4-C10 cycloalkoxyalkyl, C3-C10 alkoxyalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkoxyhaloalkyl, C2-C5 cyanoalkyl, C1-C6 hydroxyalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C8 cycloalkoxy, C3-C8 halocycloalkoxy, C4-C10 cycloalkylalkoxy, C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, C2-C8 alkoxyalkoxy, C2-C8 alkylcarbonyloxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3-C8 cycloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C1-C6 alkylamino, C2-C8 dialkylamino, C1-C6 haloalkylamino, C2-C8 halodialkylamino or C3-C8 cycloalkylamino; and

    • each R22 is independently C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C3-C8 cycloalkyl or C2-C8 alkoxyalkyl.





More particularly, this invention pertains to a compound of Formula 1 (including all stereoisomers), an N-oxide, or a salt thereof. This invention also relates to a herbicidal composition comprising a compound of the invention (i.e. in a herbicidally effective amount) and at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents. This invention further relates to a method for controlling the growth of undesired vegetation comprising contacting the vegetation or its environment with a herbicidally effective amount of a compound of the invention (e.g., as a composition described herein)


This invention also relates to a herbicidal mixture of (a) a compound of Formula 1 and (b) at least one additional active ingredient.


This invention is also directed to an intermediate compound of Formula 1Q (including all stereoisomers), N-oxides, and salts thereof:




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wherein A′ is a radical selected from the group consisting of




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and


R1, R2, B1, B2, B3, T, R9 and R10 are as defined above for a compound of Formula 1 which is useful for preparing a compound of Formula 1.


This invention is also directed to a compound of Formula 1R (including all stereoisomers), N-oxides, and salts thereof:




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    • wherein

    • R1 is phenyl, —W1(phenyl), —W1(S-phenyl), —W1(SO2-phenyl), —W2(SO2CH2-phenyl) or —W2(SCH2-phenyl), each optionally substituted on ring members with up to five substituents selected from R21; or -G or —W2G; or C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C3-C8 cycloalkyl, C4-C10 cycloalkylalkyl, C5-C12 alkylcycloalkylalkyl, C3-C8 cycloalkenyl, C3-C8 halocycloalkenyl, C2-C8 alkoxyalkyl, C3-C10 alkoxyalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl or C2-C8 alkylsulfonylalkyl;

    • W1 is C1-C6 alkylene, C2-C6 alkenylene or C2-C6 alkynylene;

    • W2 is C1-C6 alkylene;

    • R2 is phenyl or —W3(phenyl), each substituted on ring members with up to two substituents selected from R21; or -G; or C1-C6 alkyl or C3-C8 cycloalkyl;

    • W3 is C1-C6 alkylene, C2-C6 alkenylene or C2-C6 alkynylene;

    • each G is independently a 5- or 6-membered heterocyclic ring or an 8-, 9- or 10-membered fused bicyclic ring system, each ring or ring system optionally substituted with up to five substituents selected from R21 on carbon ring members and R22 on nitrogen ring members;

    • each R21 is independently halogen, cyano, hydroxy, amino, nitro, —CHO, —C(═O)OH, —C(═O)NH2, —C(═S)NH2, —C(═O)NHCN, —C(═O)NHOH, —SH, —SO2NH2, —SO2NHCN, —SO2NHOH, —OCN, —SCN, —SF5, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C4-C10 alkylcycloalkyl, C4-C10 cycloalkylalkyl, C3-C8 cycloalkenyl, C3-C8 halocycloalkenyl, C2-C8 alkoxyalkyl, C4-C10 cycloalkoxyalkyl, C3-C10 alkoxyalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkoxyhaloalkyl, C2-C5 cyanoalkyl, C1-C6 hydroxyalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C8 cycloalkoxy, C3-C8 halocycloalkoxy, C4-C10 cycloalkylalkoxy, C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, C2-C8 alkoxyalkoxy, C2-C8 alkylcarbonyloxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3-C8 cycloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C1-C6 alkylamino, C2-C8 dialkylamino, C1-C6 haloalkylamino, C2-C8 halodialkylamino or C3-C8 cycloalkylamino; and

    • each R22 is independently C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C3-C8 cycloalkyl or C2-C8 alkoxyalkyl


      which is useful for preparing a compound of Formula 1.





This invention is also directed to a compound of Formula 1S (including all stereoisomers), N-oxides, and salts thereof:




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    • wherein

    • R1 is phenyl, —W1(phenyl), —W1(S-phenyl), —W1(SO2-phenyl), —W2(SO2CH2-phenyl) or —W2(SCH2-phenyl), each optionally substituted on ring members with up to five substituents selected from R21; or -G or —W2G; or C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C3-C8 cycloalkyl, C4-C10 cycloalkylalkyl, C5-C12 alkylcycloalkylalkyl, C3-C8 cycloalkenyl, C3-C8 halocycloalkenyl, C2-C8 alkoxyalkyl, C3-C10 alkoxyalkenyl, C4-C10 alkylcycloalkyl, C4-C10 alkoxycycloalkyl, C3-C10 alkoxyalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl or C2-C8 alkylsulfonylalkyl;

    • W1 is C1-C6 alkylene, C2-C6 alkenylene or C2-C6 alkynylene;

    • W2 is C1-C6 alkylene;

    • R2 is phenyl or —W3(phenyl), each substituted on ring members with up to two substituents selected from R21; or -G; or C1-C6 alkyl or C3-C8 cycloalkyl;

    • W3 is C1-C6 alkylene, C2-C6 alkenylene or C2-C6 alkynylene;

    • each G is independently a 5- or 6-membered heterocyclic ring or an 8-, 9- or 10-membered fused bicyclic ring system, each ring or ring system optionally substituted with up to five substituents selected from R21 on carbon ring members and R22 on nitrogen ring members;

    • each R21 is independently halogen, cyano, hydroxy, amino, nitro, —CHO, —C(═O)OH, —C(═O)NH2, —C(═S)NH2, —C(═O)NHCN, —C(═O)NHOH, —SH, —SO2NH2, —SO2NHCN, —SO2NHOH, —OCN, —SCN, —SF5, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C4-C10 alkylcycloalkyl, C4-C10 cycloalkylalkyl, C3-C8 cycloalkenyl, C3-C8 halocycloalkenyl, C2-C8 alkoxyalkyl, C4-C10 cycloalkoxyalkyl, C3-C10 alkoxyalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkoxyhaloalkyl, C2-C5 cyanoalkyl, C1-C6 hydroxyalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C8 cycloalkoxy, C3-C8 halocycloalkoxy, C4-C10 cycloalkylalkoxy, C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, C2-C8 alkoxyalkoxy, C2-C8 alkylcarbonyloxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3-C8 cycloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C1-C6 alkylamino, C2-C8 dialkylamino, C1-C6 haloalkylamino, C2-C8 halodialkylamino or C3-C8 cycloalkylamino;

    • each R22 is independently C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C3-C8 cycloalkyl or C2-C8 alkoxyalkyl; and

    • R23 is an optionally substituted carbon moiety


      which is useful for preparing a compound of Formula 1.





This invention is also directed to a process for preparing a compound of Formula 1 from a compound of formula 1Q in the presence of cesium fluoride:




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wherein A′ is a radical selected from A′-1, A′-2, A′-3 and A′-5 as defined above for a compound of Formula 1Q; and A is radical selected from A-1, A-2, A-3 and A-5 as defined above for a compound of Formula 1; and R1 and R2 are as defined above for a compound of Formula 1 which is useful for preparing a compound of Formula 1.


This invention is also directed to compounds of Formula 1P (including all stereoisomers), N-oxides, and salts thereof, agricultural compositions containing them and their use as herbicides:




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wherein

    • X is CH or N;
    • Y is C(O) or S(O)2; provided that when Y is S(O)2, then X is CH;
    • A is a radical selected from the group consisting of




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    • B1 and B3 are each independently a radical selected from the group consisting of







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    • B2 is a radical selected from the group consisting of







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    • R1 is phenyl, phenylsulfonyl, —W1(phenyl), —W1(S-phenyl), —W1(SO2-phenyl), —W2(SO2CH2-phenyl) or —W2(SCH2-phenyl), each optionally substituted on ring members with up to five substituents selected from R21; or -G or —W2G; or cyano, hydroxy, amino, —C(═O)OH, —C(═O)NHCN, —C(═O)NHOH, —SO2NH2, —SO2NHCN, —SO2NHOH, —NHCHO, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C4-C10 alkylcycloalkyl, C4-C10 cycloalkylalkyl, C6-C14 cycloalkylcycloalkyl, C4-C10 halocycloalkylalkyl, C5-C12 alkylcycloalkylalkyl, C3-C8 cycloalkenyl, C3-C8 halocycloalkenyl, C2-C8 alkoxyalkyl, C4-C10 cycloalkoxyalkyl, C5-C10 cycloalkoxyalkoxyalkyl, C3-C10 alkoxyalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylaminoalkyl, C3-C10 dialkylaminoalkyl, C2-C8 haloalkylaminoalkyl, C4-C10 cycloalkylaminoalkyl, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C10 cycloalkylcarbonyl, C2-C8 alkoxycarbonyl, C4-C10 cycloalkoxycarbonyl, C5-C12 cycloalkylalkoxycarbonyl, C2-C8 alkylaminocarbonyl, C3-C10 dialkylaminocarbonyl, C4-C10 cycloalkylaminocarbonyl, C2-C5 cyanoalkyl, C1-C6 hydroxyalkyl, C4-C10 cycloalkenylalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkoxyhaloalkyl, C2-C8 haloalkoxyhaloalkyl, C4-C10 halocycloalkoxyalkyl, C4-C10 cycloalkenyloxyalkyl, C4-C10 halocycloalkenyloxyalkyl, C3-C10 dialkoxyalkyl, C3-C10 alkoxyalkylcarbonyl, C3-C10 alkoxycarbonylalkyl, C2-C8 haloalkoxycarbonyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C8 cycloalkoxy, C3-C8 halocycloalkoxy, C4-C10 cycloalkylalkoxy, C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, C2-C6 alkynyloxy, C3-C6 haloalkynyloxy, C2-C8 alkoxyalkoxy, C2-C8 alkylcarbonyloxy, C2-C8 haloalkylcarbonyloxy, C4-C10 cycloalkylcarbonyloxy, C3-C10 alkylcarbonylalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3-C8 cycloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C2-C8 alkylcarbonylthio, C2-C8 alkyl(thiocarbonyl)thio, C3-C8 cycloalkylsulfinyl, C1-C6 alkylaminosulfonyl, C2-C8 dialkylaminosulfonyl, C1-C6 alkylamino, C2-C8 dialkylamino, C1-C6 haloalkylamino, C2-C8 halodialkylamino, C3-C8 cycloalkylamino, C2-C8 alkylcarbonylamino, C2-C8 haloalkylcarbonylamino, C1-C6 alkylsulfonylamino, C1-C6 haloalkylsulfonylamino or C4-C10 cycloalkyl(alkyl)amino;

    • W1 is C1-C6 alkylene, C2-C6 alkenylene or C2-C6 alkynylene;

    • W2 is C1-C6 alkylene;

    • R2 is phenyl or —W3(phenyl), each optionally substituted on ring members with up to five substituents selected from R21; or -G or —W4G; or H, cyano, hydroxy, amino, nitro, —CHO, —C(═O)OH, —C(═O)NH2, —C(═S)NH2, —C(═O)NHCN, —C(═O)NHOH, —SH, —SO2NH2, —SO2NHCN, —SO2NHOH, —SF5, —NHCHO, —NHNH2, —NHOH, —NHCN, —NHC(═O)NH2, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C4-C10 alkylcycloalkyl, C4-C10 cycloalkylalkyl, C6-C14 cycloalkylcycloalkyl, C4-C10 halocycloalkylalkyl, C5-C12 alkylcycloalkylalkyl, C3-C8 cycloalkenyl, C3-C8 halocycloalkenyl, C2-C8 alkoxyalkyl, C4-C10 cycloalkoxyalkyl, C3-C10 alkoxyalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylaminoalkyl, C3-C10 dialkylaminoalkyl, C2-C8 haloalkylaminoalkyl, C4-C10 cycloalkylaminoalkyl, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C10 cycloalkylcarbonyl, C2-C8 alkoxycarbonyl, C4-C10 cycloalkoxycarbonyl, C5-C12 cycloalkylalkoxycarbonyl, C2-C8 alkylaminocarbonyl, C3-C10 dialkylaminocarbonyl, C4-C10 cycloalkylaminocarbonyl, C2-C5 cyanoalkyl, C1-C6 hydroxyalkyl, C4-C10 cycloalkenylalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkoxyhaloalkyl, C2-C8 haloalkoxyhaloalkyl, C4-C10 halocycloalkoxyalkyl, C4-C10 cycloalkenyloxyalkyl, C4-C10 halocycloalkenyloxyalkyl, C3-C10 dialkoxyalkyl, C3-C10 alkoxyalkylcarbonyl, C3-C10 alkoxycarbonylalkyl, C2-C8 haloalkoxycarbonyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C8 cycloalkoxy, C3-C8 halocycloalkoxy, C4-C10 cycloalkylalkoxy, C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, C2-C6 alkynyloxy, C3-C6 haloalkynyloxy, C2-C8 alkoxyalkoxy, C2-C8 alkylcarbonyloxy, C2-C8 haloalkylcarbonyloxy, C4-C10 cycloalkylcarbonyloxy, C3-C10 alkylcarbonylalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3-C8 cycloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C3-C8 trialkylsilyl, C3-C8 cycloalkenyloxy, C3-C8 halocycloalkenyloxy, C2-C8 haloalkoxyalkoxy, C2-C8 alkoxyhaloalkoxy, C2-C8 haloalkoxyhaloalkoxy, C3-C10 alkoxycarbonylalkoxy, C2-C8 alkyl(thiocarbonyl)oxy, C2-C8 alkylcarbonylthio, C2-C8 alkyl(thiocarbonyl)thio, C3-C8 cycloalkylsulfinyl, C1-C6 alkylaminosulfonyl, C2-C8 dialkylaminosulfonyl, C3-C10 halotrialkylsilyl, C1-C6 alkylamino, C2-C8 dialkylamino, C1-C6 haloalkylamino, C2-C8 halodialkylamino, C3-C8 cycloalkylamino, C2-C8 alkylcarbonylamino, C2-C8 haloalkylcarbonylamino, C1-C6 alkylsulfonylamino, C1-C6 haloalkylsulfonylamino or C4-C10 cycloalkyl(alkyl)amino;

    • W3 is C1-C6 alkylene, C2-C6 alkenylene or C2-C6 alkynylene;

    • W4 is C1-C6 alkylene;

    • R3 is H, halogen, cyano, hydroxy, —O−M+, amino, nitro, —CHO, —C(═O)OH, —C(═O)NH2, —C(═S)NH2, —SH, —SO2NH2, —SO2NHCN, —SO2NHOH, —OCN, —SCN, —SF5, —NHNH2, —NHOH, —N═C═O, —N═C═S, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C8 cycloalkoxy, C3-C8 halocycloalkoxy, C4-C10 cycloalkylalkoxy, C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, C2-C6 alkynyloxy, C3-C6 haloalkynyloxy, C2-C8 alkoxyalkoxy, C2-C8 alkylcarbonyloxy, C2-C8 haloalkylcarbonyloxy, C4-C10 cycloalkylcarbonyloxy, C3-C10 alkylcarbonylalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3-C8 cycloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C1-C6 alkylsulfonyloxy, C1-C6 alkylamino, C2-C8 dialkylamino, C1-C6 haloalkylamino, C2-C8 halodialkylamino, C3-C8 cycloalkylamino, C2-C8 alkylcarbonylamino, C2-C8 haloalkylcarbonylamino, C1-C6 alkylsulfonylamino or C1-C6 haloalkylsulfonylamino; or benzyloxy, phenyloxy, benzylcarbonyloxy, phenylcarbonyloxy, phenylsulfonyloxy, benzylsulfonyloxy, phenylthio, benzylthio, phenylsulfinyl, benzylsulfinyl, phenylsulfonyl or benzylsulfonyl, each optionally substituted on ring members with up to five substituents selected from R21;

    • M+ is an alkali metal cation or an ammonium cation;

    • R4, R5, R6 and R7 are each independently H, halogen, hydroxy, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C8 cycloalkoxy or C3-C8 halocycloalkoxy; or phenyl or benzyl, each optionally substituted on ring members with up to five substituents selected from R21;

    • R8 is H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C8 cycloalkyl or C3-C8 halocycloalkyl; or benzyl optionally substituted on ring members with up to five substituents selected from R21;

    • R9 is H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C4-C10 alkylcycloalkyl, C4-C10 cycloalkylalkyl, C6-C14 cycloalkylcycloalkyl, C4-C10 halocycloalkylalkyl, C5-C12 alkylcycloalkylalkyl, C3-C8 cycloalkenyl, C3-C8 halocycloalkenyl, C2-C8 alkoxyalkyl, C4-C10 cycloalkoxyalkyl, C3-C10 alkoxyalkoxyalkyl or C2-C8 alkylthioalkyl;

    • R10 is H, halogen, cyano, hydroxy, amino, nitro, SH, —SO2NH2, —SO2NHCN, —SO2NHOH, —OCN, —SCN, —SF5, —NHCHO, —NHNH2, —N3, —NHOH, —NHCN, —NHC(═O)NH2, —N═C═O, —N═C═S, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C4-C10 alkylcycloalkyl, C4-C10 cycloalkylalkyl, C6-C14 cycloalkylcycloalkyl, C4-C10 halocycloalkylalkyl, C5-C12 alkylcycloalkylalkyl, C3-C8 cycloalkenyl, C3-C8 halocycloalkenyl, C2-C8 alkoxyalkyl, C4-C10 cycloalkoxyalkyl, C3-C10 alkoxyalkoxyalkyl or C2-C8 alkylthioalkyl;

    • R11 is H, halogen, cyano, hydroxy, amino, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C4-C10 alkylcycloalkyl, C4-C10 cycloalkylalkyl, C4-C10 halocycloalkylalkyl, C5-C12 alkylcycloalkylalkyl, C3-C8 cycloalkenyl, C3-C8 halocycloalkenyl, C2-C8 alkoxyalkyl, C4-C10 cycloalkoxyalkyl, C3-C10 alkoxyalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl or C2-C8 alkylsulfonylalkyl; or phenyl optionally substituted with up to five substituents selected from R21;

    • R12 is H, halogen, cyano, hydroxy, amino, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C4-C10 alkylcycloalkyl, C4-C10 cycloalkylalkyl, C6-C14 cycloalkylcycloalkyl, C4-C10 halocycloalkylalkyl, C5-C12 alkylcycloalkylalkyl, C3-C8 cycloalkenyl, C3-C8 halocycloalkenyl or C2-C8 alkoxycarbonylamino;

    • R13 is H, halogen, cyano, hydroxy, amino, nitro or C2-C8 alkoxycarbonyl;

    • n is 0, 1, or 2;

    • each R14, R15, R18 and R19 is independently H, halogen, cyano, hydroxy or C1-C6 alkyl; or

    • a pair of R14 and R18 is taken together as C2-C6 alkylene or C2-C6 alkenylene;

    • R20 is H, C1-C6 haloalkyl, C2-C6 haloalkenyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C8 cycloalkoxy, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl or C3-C8 cycloalkyl;

    • T is C1-C6 alkylene or C2-C6 alkenylene;

    • each G is independently a 5- or 6-membered heterocyclic ring or an 8-, 9- or 10-membered fused bicyclic ring system, each ring or ring system optionally substituted with up to five substituents selected from R21 on carbon ring members and R22 on nitrogen ring members;

    • each R21 is independently halogen, cyano, hydroxy, amino, nitro, —CHO, —C(═O)OH, —C(═O)NH2, —C(═S)NH2, —C(═O)NHCN, —C(═O)NHOH, —SH, —SO2NH2, —SO2NHCN, —SO2NHOH, —OCN, —SCN, —SF5, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C4-C10 alkylcycloalkyl, C4-C10 cycloalkylalkyl, C3-C8 cycloalkenyl, C3-C8 halocycloalkenyl, C2-C8 alkoxyalkyl, C4-C10 cycloalkoxyalkyl, C3-C10 alkoxyalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkoxyhaloalkyl, C2-C5 cyanoalkyl, C1-C6 hydroxyalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C8 cycloalkoxy, C3-C8 halocycloalkoxy, C4-C10 cycloalkylalkoxy, C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, C2-C8 alkoxyalkoxy, C2-C8 alkylcarbonyloxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3-C8 cycloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C1-C6 alkylamino, C2-C8 dialkylamino, C1-C6 haloalkylamino, C2-C8 halodialkylamino or C3-C8 cycloalkylamino; and

    • each R22 is independently C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C3-C8 cycloalkyl or C2-C8 alkoxyalkyl.





More particularly, this invention pertains to a compound of Formula 1P (including all stereoisomers), an N-oxide, or a salt thereof. This invention also relates to a herbicidal composition comprising a compound of the invention (i.e. in a herbicidally effective amount) and at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents. This invention further relates to a method for controlling the growth of undesired vegetation comprising contacting the vegetation or its environment with a herbicidally effective amount of a compound of the invention (e.g., as a composition described herein).


This invention also includes a herbicidal mixture of (a) a compound of Formula 1P and (b) an active ingredient selected from a photosystem II inhibitor.







DETAILS OF THE INVENTION

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 or 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 claimed invention. The term “consisting essentially of” occupies a middle ground between “comprising” and “consisting of”.


Where applicants have defined an invention or a portion thereof 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 an invention 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” preceding an element or component of the invention 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, R2 and R3.


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 isomers. “Alkenylene” denotes a straight-chain or branched alkenediyl containing one olefinic bond. Examples of “alkenylene” include CH═CH, CH2CH═CH, CH═C(CH3) and the different butenylene isomers. “Alkynylene” denotes a straight-chain or branched alkynediyl containing one triple bond. Examples of “alkynylene” include C≡C, CH2C≡C, C≡CCH2 and the different butynylene 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 CH3OCH2, CH3OCH2CH2, CH3CH2OCH2, CH3CH2CH2CH2OCH2 and CH3CH2OCH2CH2. “Alkoxyalkoxy” denotes alkoxy substitution on alkoxy. “Alkenyloxy” includes straight-chain or branched alkenyloxy moieties. Examples of “alkenyloxy” include H2C═CHCH2O, (CH3)2C═CHCH2O, (CH3)CH═CHCH2O, (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. “Alkoxyalkenyl” includes straight-chain or branched alkenyl substituted by an alkoxy group. Examples of “alkoxyalkenyl” include CH3OCH═CH, CH3C(OCH3)═CH and CH3CH2OCH═CHCH2. “Alkoxyalkoxyalkyl” denotes alkoxyalkoxy substitution on alkyl. Examples of “alkoxyalkoxyalkyl” include CH3OCH2OCH2, CH3OCH2OCH2CH2, CH3CH2OCH2OCH2 and CH3OCH3CH2OCH2CH2. “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 butylsulfonyl, 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. The terms “cycloalkylsulfinyl” and “cycloalkylsulfonyl” are defined analogously to the terms “alkylsulfinyl” and “alkylsulfonyl” above.


“Alkylthioalkyl” denotes alkylthio substitution on alkyl. Examples of “alkylthioalkyl” include CH3SCH2, CH3SCH2CH2, CH3CH2SCH2, CH3CH2CH2CH2SCH2 and CH3CH2SCH2CH2; “alkylsulfinylalkyl” and “alkylsulfonylalkyl” include the corresponding sulfoxides and sulfones, respectively. “Alkylamino” includes an NH radical substituted with straight-chain or branched alkyl. Examples of “alkylamino” include CH3CH2NH, CH3CH2CH2NH, and (CH3)2CHCH2NH. Examples of “dialkylamino” include (CH3)2N, (CH3CH2CH2)2N and CH3CH2(CH3)N. “Alkylaminoalkyl” denotes alkylamino substitution on alkyl. Examples of “alkylaminoalkyl” include CH3NHCH2, CH3NHCH2CH2, CH3CH2NHCH2, CH3CH2CH2CH2NHCH2 and CH3CH2NHCH2CH2. Examples of “dialkylaminoalkyl” include ((CH3)2CH)2NCH2, (CH3CH2CH2)2NCH2 and CH3CH2(CH3)NCH2CH2. The term “alkylcarbonylamino” denotes alkyl bonded to a C(═O)NH moiety. Examples of “alkylcarbonylamino” include CH3CH2C(═O)NH and CH3 CH2CH2C(═O)NH.


“Alkylcarbonylthio” denotes a straight-chain or branched alkylcarbonyl attached to and linked through a sulfur atom. Examples of “alkylcarbonylthio” include CH3C(═O)S, CH3CH2CH2C(═O)S and (CH3)2CHC(═O)S. The term “alkyl(thiocarbonyl)oxy” refers to an alkylsulfinyl moiety group bonded to an oxygen atom. Examples of “alkyl(thiocarbonyl)oxy”, include CH3CH2OS(O) and CH3CH2CH2OS(O). The term “alkyl(thiocarbonyl)thio” refers to an alkylsulfinyl moiety bonded to a sulfur atom. Examples “alkyl(thiocarbonyl)thio” include CH3CH2S(O)S.


“Trialkylsilyl” includes 3 branched and/or straight-chain alkyl radicals attached to and linked through a silicon atom, such as trimethylsilyl, triethylsilyl and tert-butyldimethylsilyl. Examples of “halotrialkylsilyl” include CF3(CH3)2Si—, (CF3)3Si—, and CH2Cl(CH3)2Si—. “Hydroxyalkyl” denotes an alkyl group substituted with one hydroxy group. Examples of “hydroxyalkyl” include HOCH2CH2, CH3CH2(OH)CH and HOCH2CH2CH2CH2. “Cyanoalkyl” denotes an alkyl group substituted with one cyano group. Examples of “cyanoalkyl” include NCCH2, NCCH2CH2 and CH3CH(CN)CH2.


“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. The term “alkylcycloalkyl” denotes alkyl substitution on a cycloalkyl moiety. Examples of “alkylcycloalkyl” include methylcyclopropyl, ethylcyclopentyl, and other straight-chain or branched alkyl groups bonded to cycloalkyl moiety. The term “alkoxycycloalkyl” denotes alkoxy substitution on a cycloalkyl moiety. Examples of “alkoxycycloalkyl” include methoxycyclopropyl, ethoxycyclopentyl, and other straight-chain or branched alkoxy groups bonded to a cycloalkyl moiety. “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. Examples of “cyanocycloalkyl” include 4-cyanocyclohexyl and 3-cyanocyclopentyl. “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”, haloalkylsulfinyl, haloalkylsulfonyl, “haloalkenyloxy”, “haloalkynyloxy” “haloalkenyl”, “haloalkynyl”, “haloalkoxyalkyl”, “haloalkoxyalkoxy” “haloalkoxyhaloalkoxy”, “haloalkoxyhaloalkyl”, “halo alkylamino”, “haloalkylaminoalkyl” “halocycloalkoxy”, “halocycloalkoxyalkyl”, “halocycloalkylalkyl”, “halocycloalkenyl”, “halocycloalkenyloxy”, “halocycloalkenyloxy”, “halocycloalkenyloxyalkyl”, “alkoxyhaloalkoxy”, alkoxyhaloalkyl, haloalkylcarbonyloxy, and the like, are defined analogously to the term “haloalkyl”. Examples of “haloalkoxy” include CF3O—, CCl3CH2O—, HCF2CH2CH2O— and CF3CH2O—. Examples of “haloalkylthio” include CCl3S—, CF3S—, CCl3CH2S— and ClCH2CH2CH2S—. 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 (Cl)2C═CHCH2— and CF3CH2CH═CHCH2—. Examples of “haloalkynyl” include HC≡CCHCl—, CF3C≡C—, CCl3C≡C— and FCH2C≡CCH2—. Examples of “haloalkoxyalkoxy” include CF3OCH2O—, ClCH2CH2OCH2CH2O—, Cl3CCH2OCH2O— as well as branched alkyl derivatives. Examples of “haloalkylamino” include CF3(CH3)CHNH, (CF3)2CHNH and CH2ClCH2NH. The term “halodialkyl”, either alone or in compound words such as “halodialkylamino”, means at least one of the two alkyl groups is substituted with at least one halogen atom, and independently each halogenated alkyl group may be partially or fully substituted with halogen atoms which may be the same or different. Examples of “halodialkylamino” include (BrCH2CH2)2N and BrCH2CH2(ClCH2CH2)N.


“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)—, CH3CH2CH2OC(═O)—, (CH3)2CHOC(═O)— and the different butoxy- or pentoxycarbonyl isomers. The terms “haloalkylcarbonyl” “haloalkoxycarbonyl”, “alkoxyalkylcarbonyl”, “cycloalkoxycarbonyl”, “cycloalkylalkoxycarbonyl”, “cycloalkylaminocarbonyl” are defined analogously.


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—. Examples of “alkylaminocarbonyl” include CH3NHC(═O), CH3CH2NHC(═O), CH3CH2CH2NHC(═O), (CH3)2CHNHC(═O) and the different butylamino- or pentylaminocarbonyl isomers. Examples of “dialkylaminocarbonyl” include (CH3)2NC(═O), (CH3CH2)2NC(═O), CH3CH2(CH3)NC(═O), (CH3)2CH(CH3)NC(═O) and CH3CH2CH2(CH3)NC(═O). The term “alkylcarbonyloxy” denotes straight-chain or branched alkyl bonded to a C(═O)O moiety. Examples of “alkylcarbonyloxy” include CH3CH2C(═O)O and (CH3)2CHC(═O)O. The term “alkylcarbonylalkoxy” denotes alkylcarbonyl bonded to an alkoxy moiety. Examples of “alkylcarbonylalkoxy” include CH3C(═O)CH2CH2O and CH3CH2C(═O)CH2O. Examples of “alkoxycarbonyloxy” include CH3CH2CH2OC(═O)O and (CH3)2CHOC(═O)O. The term “cycloalkylcarbonyloxy” denotes a cycloalkylcarbonyl group bonded to oxygen. Examples of “cycloalkylcarbonyloxy” include c-Pr—C(O)O— and c-hexyl-C(O)O—.


“Alkylsulfonylamino” denotes an NH radical substituted with alkylsulfonyl. Examples of “alkylsulfonylamino” include CH3CH2S(═O)2NH— and (CH3)2CHS(═O)2NH—. The term “alkylsulfonyloxy” denotes an alkylsulfonyl group bonded to an oxygen atom. Examples of “alkylsulfonyloxy” include CH3S(═O)2O —, CH3CH2S(═O)2O—, CH3CH2CH2S(═O)2O—, (CH3)2CHS(═O)2O—, and the different butylsulfonyloxy, pentylsulfonyloxy and hexylsulfonyloxy isomers.


The term “cycloalkoxyalkyl” denotes cycloalkoxy substitution on an alkyl moiety. Examples of “cycloalkoxyalkyl” include cyclopropyloxymethyl, cyclopentyloxyethyl, and other cycloalkoxy moieties bonded to straight-chain or branched alkyl groups. The term “cycloalkylthio” denotes cycloalkyl attached to and linked through a sulfur atom such as cyclopropylthio and cyclopentylthio; “cycloalkylsulfonyl” includes the corresponding sulfones. “Alkylcycloalkylalkyl” denotes an alkyl group substituted with alkylcycloalkyl. Examples of “alkylcycloalkylalkyl” include 1-, 2-, 3- or 4-methyl or -ethyl cyclohexylmethyl. The term “cycloalkoxyalkoxyalkyl” denotes a cycloalkoxy moiety attached to an alkoxyalkyl group. Examples of the term “cycloalkoxyalkoxyalkyl” include (tetrahydrofuran-2-yl)CH2OCH2—, (tetrahydrofuran-3-yl)CH2CH2O CH2— or (oxiran-2-yl)CH2OCH2CH2—. The term “cycloalkylcycloalkyl” denotes cycloalkyl substitution on another cycloalkyl ring, wherein each cycloalkyl ring independently has from 3 to 7 carbon atom ring members. Examples of cycloalkylcycloalkyl include cyclopropylcyclopropyl (such as 1,1′-bicyclopropyl-1-yl, 1,1′-bicyclopropyl-2-yl), cyclohexylcyclopentyl (such as 4-cyclopentylcyclohexyl) and cyclohexylcyclohexyl (such as 1,1′-bicyclohexyl-1-yl), and the different cis- and trans-cycloalkylcycloalkyl isomers, (such as (1R,2S)-1,1′-bicyclopropyl-2-yl and (1R,2R)-1,1′-bicyclopropyl-2-yl).


“Dialkoxyalkyl” denotes two independent alkoxy groups substituted on same carbon of the alkyl group. Examples of “dialkoxyalkyl” include (CH3O)2CH— and CH3CH2O(CH3O)CH—. “Cycloalkylamino” denotes an NH radical substituted with cycloalkyl. Examples of “cycloalkylamino” include cyclopropylamino and cyclohexylamino. “Cycloalkyl(alkyl)amino” means a cycloalkylamino group where the hydrogen atom is replaced by an alkyl radical. Examples of “cycloalkyl(alkyl)amino” include groups such as cyclopropyl(methyl)amino, cyclobutyl(butyl)amino, cyclopentyl(propyl)amino, cyclohexyl(methyl)amino and the like. The term “cycloalkylaminoalkyl” denotes cycloalkylamino substitution on an alkyl group. Examples of “cycloalkylaminoalkyl” include cyclopropylaminomethyl, cyclopentylaminoethyl, and other cycloalkylamino moieties bonded to straight-chain or branched alkyl groups.


“Cycloalkylcarbonyl” denotes cycloalkyl bonded to a C(═O) group including, for example, cyclopropylcarbonyl and cyclopentylcarbonyl. The term “cycloalkoxycarbonyl” means cycloalkoxy bonded to a C(═O) group, for example, cyclopropyloxycarbonyl and cyclopentyloxycarbonyl. “Cycloalkylaminocarbonyl” denotes cycloalkylamino bonded to a C(═O) group, for example, cyclopentylaminocarbonyl and cyclohexylaminocarbonyl. “Cycloalkylalkoxycarbonyl” denotes cycloalkylalkoxy bonded to a C(═O) group. Examples of “cycloalkylalkoxycarbonyl” include cyclopropylethoxycarbonyl and cyclopentylmethoxycarbonyl. “Cycloalkylcarbonyloxy” denotes cycloalkylcarbonyl attached to and linked through an oxygen atom. Examples of “cycloalkylcarbonyloxy” include cyclohexylcarbonyloxy and cyclopentylcarbonyloxy.


The term “cycloalkenylalkyl” denotes cycloalkenyl substitution on an alkyl moiety. Examples of “cycloalkenylalkyl” include cyclobutenylmethyl, cyclopentenylethyl, and other cycloalkenyl moieties bonded to straight-chain or branched alkyl groups. The term “cycloalkenyloxy” denotes cycloalkenyl linked through an oxygen atom such as cyclopentenyloxy and cyclohexenyloxy. The term “cycloalkenyloxyalkyl” denotes cycloalkenyloxy substitution on an alkyl moiety. Examples of “cycloalkenyloxyalkyl” include cyclobutenyloxymethyl, cyclopentenyloxyethyl, and other cycloalkenyloxy moieties bonded to straight-chain or branched alkyl groups.


The term “alkylaminosulfonyl” denotes a straight-chain or branched alkylamino moiety bonded to a sulfonyl group. Examples of an “alkylaminosulfonyl” group include CH3NHS(O)2— or CH3CH2CH2NHS(O)2—. The term “dialkylaminosulfonyl” denotes a straight-chain or branched dialkylamino moiety bonded to a sulfonyl group. Examples of a “dialkylaminosulfonyl” group include (CH3)2NS(O)2— or (CH3CH2CH2)2NS(O)2—.


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 14. 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., (Rv)r, r is 1, 2, 3, 4 or 5 in U-1 of Exhibit 2. When a group contains a substituent which can be hydrogen, for example R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, R18, R19 or R20, 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 (Rv)r in Q-29 of Exhibit 1 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.


Unless otherwise indicated, a “ring” or “ring system” as a component of Formula 1 (e.g., substituent G) 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 “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 Hückel'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 Hückel'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) π electrons, where n is a positive integer, are associated with the ring to comply with Hückel's rule. The term “aromatic ring system” denotes a carbocyclic or heterocyclic ring system in which at least one ring of the ring system is aromatic. 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” denotes a carbocylcic 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.


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 G is a 5- or 6-membered nitrogen-containing heterocyclic ring, it may be attached to the remainder of Formula 1 through any available carbon or nitrogen ring atom, unless otherwise described. When G is (among others) a 5- or 6-membered heterocyclic ring it may be saturated or unsaturated, optionally substituted with one or more substituents selected from a group of substituents as defined in the Summary of the Invention. Examples of a 5- or 6-membered unsaturated aromatic heterocyclic ring optionally substituted with from one or more substituents include the rings Q-1 through Q-60 illustrated in Exhibit 1 wherein Rv is any substituent as defined in the Summary of the Invention for R21 on carbon ring members or R22 on nitrogen ring members, and r is an integer from 0 to 4, limited by the number of available positions on each Q group. As Q-29, Q-30, Q-36, Q-37, Q-38, Q-39, Q-40, Q-41, Q-42 and Q-43 have only one available position, for these Q groups r is limited to the integers 0 or 1, and r being 0 means that the Q group is unsubstituted and a hydrogen is present at the position indicated by (Rv)r.




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Note that when G is a 5- or 6-membered saturated or unsaturated non-aromatic heterocyclic ring optionally substituted with one or more substituents selected from the group of substituents as defined in the Summary of the Invention for R21 one or two carbon ring members of the heterocycle can optionally be in the oxidized form of a carbonyl moiety.


Examples of a 5- or 6-membered saturated or non-aromatic unsaturated heterocyclic ring include the rings U-1 through U-36 as illustrated in Exhibit 2. 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. The optional substituents corresponding to Rv can be attached to any available carbon or nitrogen by replacing a hydrogen atom. For these U rings, r is typically an integer from 0 to 4, limited by the number of available positions on each U group.


Note that when G comprises a ring selected from U-29 through U-36, U2 is selected from O, S or N. Note that when U2 is N, the nitrogen atom can complete its valence by substitution with either H or the substituents corresponding to Rv as defined in the Summary of the Invention for U (i.e. R22).




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As noted above, G can be (among others) an 8-, 9- or 10-membered fused bicyclic ring system optionally substituted with one or more substituents selected from a group of substituents as defined in the Summary of the Invention (i.e. R21). Examples of 8-, 9- or 10-membered fused bicyclic ring system optionally substituted with from one or more substituents include the rings Q-81 through Q-123 illustrated in Exhibit 3 wherein Rv is any substituent as defined in the Summary of the Invention for G (i.e. R21 or R22), and r is typically an integer from 0 to 4.




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Although Rv groups are shown in the structures Q-1 through Q-60 and Q-81 through Q-123, it is noted that they do not need to be present since they are optional substituents. The nitrogen atoms that require substitution to fill their valence are substituted with H or Rv. Note that when the attachment point between (Rv)r and the Q group is illustrated as floating, (Rv)r can be attached to any available carbon atom or nitrogen atom of the Q group. Note that when the attachment point on the Q group is illustrated as floating, the Q group can be attached to the remainder of Formula 1 through any available carbon or nitrogen of the Q group by replacement of a hydrogen atom. Note that some Q groups can only be substituted with less than 4 Rv groups (e.g., Q-1 through Q-5, Q-7 through Q-48, and Q-52 through Q-60).


As noted in the Summary of the Invention, R1 and R2 are taken together along with the atoms to which they are attached to make a 5-, 6- or 7-membered unsaturated, partially unsaturated or fully unsaturated ring along with members consisting of up to 2 oxygen atoms, 2 nitrogen atoms or 2 sulfur atoms or up to two —S(O)—, —S(O)2—, —C(O)— groups. Besides the possibility of R1 and R2 being separate substituents, they may also be connected to form a ring fused to the ring to which they are attached. The fused ring can be a 5-, 6- or 7-membered ring including as ring members the two atoms shared with the ring to which the substituents are attached. The other 3, 4 or 5 ring members of the fused ring are provided by R1 and R2 substituents taken together. These other ring members can include up to 5 carbon atoms (as allowed by the ring size) and optionally up to 3 heteroatoms selected from up to 2 O, up to 2 S and up to 3 N. The fused ring is optionally substituted with up to 3 substituents as noted in the Summary of the Invention. Exhibit 4 provides, as illustrative examples, rings formed by R1 and R2 taken together. As these rings are fused with a ring of Formula 1, a portion of the Formula 1 ring is shown and the truncated lines represent the ring bonds of the Formula 1 ring. The rings depicted are fused to the two adjacent atoms of a ring as shown in Formula 1. The optional substituents (Rv)r, are independently selected from the group consisting of halogen, cyano, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C3-C8 cycloalkyl and C2-C8 alkoxyalkyl; and phenyl optionally substituted with up to 5 substituents selected from cyano, nitro, halogen, C1-C6 alkyl, C1-C6 alkoxy and C1-C6 haloalkoxy; on carbon atom ring members. The optional substituents (Rv)r, are independently selected from the group consisting of H and C1-C6 alkyl; and phenyl optionally substituted with up to 5 substituents selected from cyano, nitro, halogen, C1-C6 alkyl, C1-C6 alkoxy and C1-C6 haloalkoxy; on nitrogen ring members. Substituents are limited by the number of available positions on each T-ring. When the attachment point between (Rv)r and the T-ring is illustrated as floating, Rv may be bonded to any available T-ring carbon or nitrogen atom (as applicable). One skilled in the art recognizes that while r is nominally an integer from 0 to 3, some of the rings shown in Exhibit 4 have less than 3 available positions, and for these groups r is limited to the number of available positions. When “r” is 0 this means the ring is unsubstituted and hydrogen atoms are present at all available positions. If r is 0 and (Rv)r is shown attached to a particular atom, then hydrogen is attached to that atom. The nitrogen atoms that require substitution to fill their valence are substituted with H or Rv. Furthermore, one skilled in the art recognizes that some of the rings shown in Exhibit 4 can form tautomers, and the particular tautomer depicted is representative of all the possible tautomers.




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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 II, A. R. Katritzky, C. W. Rees and E. F. V. Scriven editors-in-chief, Pergamon Press, Oxford, 1996.


Compounds of this invention can exist as one or more stereoisomers. The various stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers. 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. The compounds of the invention may be present as a mixture of stereoisomers, individual stereoisomers or as an optically active form.


One skilled in the art will recognize that when A is A-1, A-2 or A-3, and the R3 variable is hydroxy or O−M+, then the resulting compound of Formula 1 can exist in either the “triketone” tautomer or the “di-keto enol” tautomer. Likewise, when A is A-1, A-2 or A-3, and the R3 variable is —SH, the resulting compound of Formula 1 can exist in either the the “di-keto thioketo” tautomer or the “di-keto thioenol” tautomer. In any of these cases and for the purposes of this invention both tautomeric combinations represent fully functional species of the present invention. For example, named species using the phrase “2-(1,3-cyclohexanedione)” is synonymous with the term “3-oxo-1-cyclohexen-1-yl”.


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.


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 invention comprises compounds selected from Formula 1, N-oxides and agriculturally suitable salts thereof.


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

    • Embodiment 1. A compound of Formula 1 wherein A is A-1, A-3, A-4, A-5 or A-6.
    • Embodiment 2. A compound of Embodiment 1 wherein A is A-1, A-3, A-5 or A-6.
    • Embodiment 3. A compound of Embodiment 2 wherein A is A-1, A-3 or A-5.
    • Embodiment 4. A compound of Embodiment 3 wherein A is A-1 or A-3.
    • Embodiment 5. A compound of Embodiment 4 wherein A is A-1.
    • Embodiment 6. A compound of Embodiment 4 wherein A is A-3.
    • Embodiment 7. A compound of Formula 1 or any one of Embodiments 1 through 5 wherein A is other than A-1.
    • Embodiment 8. A compound of Formula 1 or any one of Embodiments 1 through 7 wherein B1 is C-1.
    • Embodiment 9. A compound of Formula 1 or any one of Embodiments 1 through 7 wherein B1 is C-2.
    • Embodiment 10. A compound of Formula 1 or any one of Embodiments 1 through 9 wherein B2 is C-3.
    • Embodiment 11. A compound of Formula 1 or any one of Embodiments 1 through 9 wherein B2 is C-4.
    • Embodiment 12. A compound of Formula 1 or any one of Embodiments 1 through 11 wherein B3 is C-1.
    • Embodiment 13. A compound of Formula 1 or any one of Embodiments 1 through 11 wherein B3 is C-2.
    • Embodiment 14. A compound of Formula 1 or any one of Embodiments 1 through 13 wherein R1 is phenyl, phenylsulfonyl, —W1(phenyl), —W1(S-phenyl), —W1(SO2-phenyl), —W2(SO2CH2-phenyl) or —W2(SCH2-phenyl), each optionally substituted on ring members with up to five substituents selected from R21; or -G or —W2G; or cyano, hydroxy, amino, —C(═O)OH, —C(═O)NHCN, —C(═O)NHOH, —SO2NH2, —SO2NHCN, —SO2NHOH, —NHCHO, C1-C10 alkyl, C2-C10 alkenyl, C2-C10 alkynyl, C1-C10 haloalkyl, C2-C10 haloalkenyl, C2-C12 haloalkynyl, C3-C12 cycloalkyl, C3-C12 halocycloalkyl, C4-C14 alkylcycloalkyl, C4-C14 cycloalkylalkyl, C6-C18 cycloalkylcycloalkyl, C4-C14 halocycloalkylalkyl, C5-C16 alkylcycloalkylalkyl, C3-C12 cycloalkenyl, C3-C12 halocycloalkenyl, C2-C12 alkoxyalkyl, C3-C12 alkoxyalkenyl, C4-C14 alkylcycloalkyl, C4-C14 alkoxycycloalkyl, C4-C14 cycloalkoxyalkyl, C5-C14 cycloalkoxyalkoxyalkyl, C3-C14 alkoxyalkoxyalkyl, C2-C12 alkylthioalkyl, C2-C12 alkylsulfinylalkyl, C2-C12 alkylsulfonylalkyl, C2-C12 alkylaminoalkyl, C3-C14 dialkylaminoalkyl, C2-C12 haloalkylaminoalkyl, C4-C14 cycloalkylaminoalkyl, C2-C12 alkylcarbonyl, C2-C12 haloalkylcarbonyl, C4-C14 cycloalkylcarbonyl, C2-C12 alkoxycarbonyl, C4-C16 cycloalkoxycarbonyl, C5-C14 cycloalkylalkoxycarbonyl, C2-C12 alkylaminocarbonyl, C3-C14 dialkylaminocarbonyl, C4-C14 cycloalkylaminocarbonyl, C2-C9 cyanoalkyl, C1-C10 hydroxyalkyl, C4-C14 cycloalkenylalkyl, C2-C12 haloalkoxyalkyl, C2-C12 alkoxyhaloalkyl, C2-C12 haloalkoxyhaloalkyl, C4-C14 halocycloalkoxyalkyl, C4-C14 cycloalkenyloxyalkyl, C4-C14 halocycloalkenyloxyalkyl, C3-C14 dialkoxyalkyl, C3-C14 alkoxyalkylcarbonyl, C3-C14 alkoxycarbonylalkyl or C2-C12 haloalkoxycarbonyl.
    • Embodiment 15. A compound of Formula 1 or any one of Embodiments 1 through 14 wherein R1 is phenyl, phenylsulfonyl, —W1(phenyl), —W1(S-phenyl), —W1(SO2-phenyl), —W2(SO2CH2-phenyl) or —W2(SCH2-phenyl), each optionally substituted on ring members with up to five substituents selected from R21; or -G or —W2G; or cyano, hydroxy, amino, —C(═O)OH, —C(═O)NHCN, —C(═O)NHOH, —SO2NH2, —SO2NHCN, —SO2NHOH, —NHCHO, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C4-C10 alkylcycloalkyl, C4-C10 cycloalkylalkyl, C6-C14 cycloalkylcycloalkyl, C4-C10 halocycloalkylalkyl, C5-C12 alkylcycloalkylalkyl, C3-C8 cycloalkenyl, C3-C8 halocycloalkenyl, C2-C8 alkoxyalkyl, C3-C10 alkoxyalkenyl, C4-C10 alkylcycloalkyl, C4-C10 alkoxycycloalkyl, C4-C10 cycloalkoxyalkyl, C3-C10 alkoxyalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylaminoalkyl, C3-C10 dialkylaminoalkyl, C2-C8 haloalkylaminoalkyl, C4-C10 cycloalkylaminoalkyl, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C10 cycloalkylcarbonyl, C2-C8 alkoxycarbonyl, C4-C10 cycloalkoxycarbonyl, C5-C12 cycloalkylalkoxycarbonyl, C2-C8 alkylaminocarbonyl, C3-C10 dialkylaminocarbonyl, C4-C10 cycloalkylaminocarbonyl, C2-C5 cyanoalkyl, C1-C6 hydroxyalkyl, C4-C10 cycloalkenylalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkoxyhaloalkyl, C2-C8 haloalkoxyhaloalkyl, C4-C10 halocycloalkoxyalkyl, C4-C10 cycloalkenyloxyalkyl, C4-C10 halocycloalkenyloxyalkyl, C3-C10 dialkoxyalkyl, C3-C10 alkoxyalkylcarbonyl, C3-C10 alkoxycarbonylalkyl or C2-C8 haloalkoxycarbonyl.
    • Embodiment 16. A compound of Embodiment 15 wherein R1 is phenyl, —W1(phenyl), —W1(S-phenyl), —W1(SO2-phenyl), —W2(SO2CH2-phenyl) or —W2(SCH2-phenyl), each optionally substituted on ring members with up to five substituents selected from R21; or -G or —W2G; or C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C3-C8 cycloalkyl, C4-C10 cycloalkylalkyl, C5-C12 alkylcycloalkylalkyl, C3-C8 cycloalkenyl, C3-C8 halocycloalkenyl, C2-C8 alkoxyalkyl, C3-C10 alkoxyalkenyl, C4-C10 alkylcycloalkyl, C4-C10 alkoxycycloalkyl, C3-C10 alkoxyalkoxyalkyl, C2-C8 alkylthioalkyl or C2-C8 alkylsulfonylalkyl.
    • Embodiment 17. A compound of Embodiment 16 wherein R1 is phenyl or —W1(phenyl), each optionally substituted on ring members with up to two substituents selected from R21; or -G or —W2G; or C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C3-C8 cycloalkyl, C4-C10 cycloalkylalkyl, C5-C12 alkylcycloalkylalkyl, C3-C8 cycloalkenyl, C3-C8 halocycloalkenyl, C2-C8 alkoxyalkyl C3-C10 alkoxyalkenyl, C4-C10 alkylcycloalkyl or C4-C10 alkoxycycloalkyl.
    • Embodiment 18. A compound of Embodiment 17 wherein R1 is phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 4-methylphenyl, 4-ethylphenyl, 2-methylphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 3,5-dimethylphenyl, 3,4-dimethoxyphenyl, 2,3-dimethylphenyl, 3-fluoro-2-methylphenyl, 4-fluoro-3-methylphenyl or 5-chloro-2-methylphenyl.
    • Embodiment 19. A compound of Embodiment 18 wherein R1 is phenyl, 4-ethylphenyl, 4-methoxyphenyl, 3,5-dimethylphenyl, 3,4-dimethoxyphenyl, 3-fluoro-2-methylphenyl, 4-fluoro-3-methylphenyl or 5-chloro-2-methylphenyl.
    • Embodiment 20. A compound of Embodiment 19 wherein R1 is phenyl, 3,4-dimethoxyphenyl or 5-chloro-2-methylphenyl.
    • Embodiment 21. A compound of Embodiment 20 wherein R1 is phenyl.
    • Embodiment 22. A compound of Embodiment 19 wherein R1 is 3,4-dimethoxyphenyl.
    • Embodiment 23. A compound of Embodiment 19 wherein R1 is 5-chloro-2-methylphenyl.
    • Embodiment 24. A compound of Formula 1 or any one of Embodiments 1 through 21 wherein R1 is other than phenyl.
    • Embodiment 25. A compound of Embodiment 17 wherein R1 is -G or —W2G; C1-C6 alkyl, C3-C8 cycloalkyl, or C2-C8 alkoxyalkyl.
    • Embodiment 26. A compound of Embodiment 25 wherein R1 is -G or —W2G.
    • Embodiment 27. A compound of Embodiment 26 wherein R1 is C1-C6 alkyl, C3-C8 cycloalkyl, or C2-C8 alkoxyalkyl.
    • Embodiment 28. A compound of Embodiment 27 wherein R1 is n-Pr, i-Pr, n-Bu, c-hexyl, c-heptyl, —CH2CH2OCH3, —CH2CH2CH2OCH3 or —CH2CH2OCH2CH3.
    • Embodiment 29. A compound of Embodiment 28 wherein R1 is n-Pr, c-hexyl, —CH2CH2OCH3 or —CH2CH2CH2OCH3.
    • Embodiment 29a. A compound of Embodiment 29 wherein R1 is n-Pr or —CH2CH2OCH3.
    • Embodiment 29b. A compound of Embodiment 29 wherein R1 is c-hexyl.
    • Embodiment 30. A compound of Formula 1 or any one of Embodiments 1 through 17 wherein W1 is C1-C6 alkylene.
    • Embodiment 31. A compound of Embodiment 30 wherein W1 is —CH2—.
    • Embodiment 32. A compound of Formula 1 or any one of Embodiments 1 through 17, 25 or 26 wherein W2 is —CH2—.
    • Embodiment 33. A compound of Formula 1 or any one of Embodiments 1 through 32 wherein R2 is phenyl or —W3(phenyl), each optionally substituted on ring members with up to five substituents selected from R21; or -G; C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C4-C10 alkylcycloalkyl, C4-C10 cycloalkylalkyl, C6-C14 cycloalkylcycloalkyl, C4-C10 halocycloalkylalkyl, C5-C12 alkylcycloalkylalkyl, C3-C8 cycloalkenyl, C3-C8 halocycloalkenyl, C2-C8 alkoxyalkyl, C3-C10 alkoxyalkenyl, C4-C10 cycloalkoxyalkyl, C4-C10 cycloalkoxylalkoxyalkyl, C3-C10 alkoxyalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylcarbonyl, C4-C10 cycloalkenylalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkoxyhaloalkyl, C2-C8 haloalkoxyhaloalkyl, C4-C10 halocycloalkoxyalkyl, C4-C10 cycloalkenyloxyalkyl, C4-C10 halocycloalkenyloxyalkyl, C3-C10 dialkoxyalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C8 cycloalkoxy, C3-C8 halocycloalkoxy, C4-C10 cycloalkylalkoxy, C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, C2-C6 alkynyloxy, C3-C6 haloalkynyloxy, C2-C8 alkoxyalkoxy, C2-C8 alkylcarbonyloxy, C2-C8 haloalkylcarbonyloxy, C4-C10 cycloalkylcarbonyloxy, C3-C10 alkylcarbonylalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3-C8 cycloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C3-C8 trialkylsilyl, C3-C8 cycloalkenyloxy, C3-C8 halocycloalkenyloxy, C2-C8 haloalkoxyalkoxy, C2-C8 alkoxyhaloalkoxy, C2-C8 haloalkoxyhaloalkoxy, C3-C10 alkoxycarbonylalkoxy, C2-C8 alkyl(thiocarbonyl)oxy, C3-C8 cycloalkylsulfinyl or C3-C10 halotrialkylsilyl.
    • Embodiment 34. A compound of Embodiment 33 wherein R2 is phenyl or —W3(phenyl), each optionally substituted on ring members with up to two substituents selected from R21; or -G or; or C1-C6 alkyl or C3-C8 cycloalkyl.
    • Embodiment 35. A compound of Embodiment 34 wherein R2 is phenyl optionally substituted on ring members with up to two substituents selected from R21; or -G; or C1-C6 alkyl, C3-C8 cycloalkyl.
    • Embodiment 36. A compound of Embodiment 35 wherein R2 is phenyl, 2-methylphenyl, 3-methylphenyl, 4-chlorophenyl, 3-fluorophenyl or 3,5-difluorophenyl.
    • Embodiment 36a. A compound of Embodiment 35 wherein R2 is phenyl, 3-bromophenyl, 3-chlorophenyl, or 2-methylphenyl.
    • Embodiment 37. A compound of Embodiment 35 wherein R2 is phenyl.
    • Embodiment 38. A compound of Formula 1 or any one of Embodiments 1 through 36 wherein R2 is other than phenyl.
    • Embodiment 39. A compound of Embodiment 35 wherein R2 is 3-thienyl or 2-thienyl.
    • Embodiment 40. A compound of Embodiment 35 wherein R2 is n-propyl, n-butyl, or cyclopropyl.
    • Embodiment 41. A compound of Formula 1 or any one of Embodiments 1 through 13 wherein R1 and R2 are taken together along with the atoms to which they are attached to make a 6- or 7-membered unsaturated, partially unsaturated or fully unsaturated ring along with members consisting of up to 2 oxygen atoms, 2 nitrogen atoms or 2 sulfur atoms or up to two —S(O)—, —S(O)2—, —C(O)— groups optionally substituted on carbon atom ring members selected from halogen, cyano, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C3-C8 cycloalkyl and C2-C8 alkoxyalkyl; and phenyl optionally substituted with up to 5 substituents selected from cyano, nitro, halogen, C1-C6 alkyl, C1-C6 alkoxy and C1-C6 haloalkoxy; and optionally substituted on nitrogen ring members selected from H and C1-C6 alkyl; and phenyl optionally substituted with up to 5 substituents selected from cyano, nitro, halogen, C1-C6 alkyl, C1-C6 alkoxy and C1-C6 haloalkoxy.
    • Embodiment 42. A compound of Embodiment 41 wherein R1 and R2 are taken together along with the atoms to which they are attached to make a 6- or 7-membered unsaturated, partially unsaturated or fully unsaturated ring along with members consisting of up to 1 oxygen atoms, 1 nitrogen atoms or 1 sulfur atoms or up to one —S(O)—, —S(O)2—, —C(O)— groups optionally substituted on carbon atom ring members selected from halogen, cyano, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C3-C8 cycloalkyl and C2-C8 alkoxyalkyl; and optionally substituted on nitrogen ring members selected from H and C1-C6 alkyl.
    • Embodiment 43. A compound of Embodiment 42 wherein R1 and R2 are taken together along with the atoms to which they are attached to make a 7-membered partially unsaturated ring optionally substituted with halogen, cyano, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C3-C8 cycloalkyl or C2-C8 alkoxyalkyl on carbon atom ring members.
    • Embodiment 44. A compound of Embodiment 43 wherein R1 and R2 are taken together along with the atoms to which they are attached to make an unsubstituted 7-membered partially unsaturated ring.
    • Embodiment 45. A compound of Formula 1 or any one of Embodiments 1 through 34 wherein W3 is —CH2—.
    • Embodiment 46. A compound of Formula 1 or any one of Embodiments 1 through 32 wherein W4 is —CH2—.
    • Embodiment 47. A compound of Formula 1 or any one of Embodiments 1 through 46 wherein R3 is hydroxy, —O−M+, C2-C8 alkylcarbonyloxy, C2-C8 haloalkylcarbonyloxy, C4-C10 cycloalkylcarbonyloxy or C3-C10 alkylcarbonylalkoxy; or benzyloxy, phenyloxy, benzylcarbonyloxy, phenylcarbonyloxy, phenylsulfonyloxy or benzylsulfonyloxy, each optionally substituted on ring members with up to two substituents selected from R21.
    • Embodiment 48. A compound of Embodiment 47 wherein R3 is hydroxy, —O−M+ or C2-C8 alkylcarbonyloxy; or phenylsulfonyloxy optionally substituted with up to two substituents selected from R21.
    • Embodiment 49. A compound of Embodiment 48 wherein M+ is a sodium or potassium metal cation.
    • Embodiment 50. A compound of Embodiment 49 wherein R3 is hydroxy or C2-C8 alkylcarbonyloxy.
    • Embodiment 51. A compound of Embodiment 50 wherein R3 is hydroxy or —OC(═O)CH2CH(CH3)2.
    • Embodiment 52. A compound of Formula 1 or any one of Embodiments 1, 7 and 14 through 51 wherein R4, R5, R6 and R7 are each independently H, or C1-C6 alkyl.
    • Embodiment 53. A compound of Formula 1 or any one of Embodiments 1, 7 and 14 through 52 wherein R8 is C1-C6 alkyl or C3-C8 cycloalkyl.
    • Embodiment 54. A compound of Embodiment 53 wherein R8 is CH3, CH2CH3 or cyclopropyl.
    • Embodiment 55. A compound of Formula 1 or any one of Embodiments 1 through 3, 7 and 14 through 51 wherein R9 is C1-C6 alkyl.
    • Embodiment 56. A compound of Embodiment 55 wherein R9 is CH2CH3.
    • Embodiment 57. A compound of Formula 1 or any one of Embodiments 1 through 3, 7 and 14 through 51 wherein R10 is H, halogen or C1-C6 alkyl.
    • Embodiment 58. A compound of Embodiment 57 wherein R10 is H or CH3.
    • Embodiment 59. A compound of Formula 1 or any one of Embodiments 1, 2, 8, 10 and 12 through 51 wherein R11 is H or C1-C6 alkyl.
    • Embodiment 60. A compound of Embodiment 59 wherein R11 is H.
    • Embodiment 61. A compound of Formula 1 or any one of Embodiments 1, 2, 8, 10 and 12 through 51 wherein R12 is H, halogen, cyano, hydroxy, amino or C1-C6 alkyl.
    • Embodiment 62. A compound of Embodiment 61 wherein R12 is H, halogen, cyano, C1-C6 alkyl or C3-C8 cycloalkyl.
    • Embodiment 63. A compound of Embodiment 62 wherein R12 is CH3, CH2CH3 or cyclopropyl.
    • Embodiment 64. A compound of Formula 1 or any one of Embodiments 7 and 15 through 51 wherein R13 is H, halogen, cyano or nitro.
    • Embodiment 65. A compound of Embodiment 64 wherein R13 is cyano or nitro.
    • Embodiment 66. A compound of Formula 1 or any one of Embodiments 1 through 65 wherein when instances of R14 and R18 are taken alone (i.e. R14 and R18 are not taken together as alkylene or alkenylene), then independently said instances of R14 and R18 are H or C1-C6 alkyl.
    • Embodiment 67. A compound of Embodiment 66 wherein when instances of R14 and R18 are taken alone, then independently said instances of R14 and R18 are H or CH3.
    • Embodiment 68. A compound of Embodiment 68 wherein when instances of R14 and R18 are taken alone, then independently said instances of R14 and R18 are H.
    • Embodiment 69. A compound of Formula 1 or any one of Embodiments 1 through 68 wherein when instances of R14 and R18 are taken together, then said instances of R14 and R18 are taken together as —CH2CH2CH2— or —CH═CHCH2—.
    • Embodiment 70. A compound of Formula 1 or any one of Embodiments 1 through 68 wherein all instances of R14 and R18 are taken alone.
    • Embodiment 71. A compound of Formula 1 or any one of Embodiments 1 through 70 wherein independently each R15 and R19 is H or C1-C6 alkyl.
    • Embodiment 72. A compound of Embodiment 71 wherein independently each R15 and R19 is H or CH3.
    • Embodiment 73. A compound of Embodiment 72 wherein independently each R15 and R19 is H.
    • Embodiment 73a. A compound of Embodiments 67 and 72 wherein each R14, R15, R18 and R19 is H or CH3.
    • Embodiment 73b. A compound of Embodiment 73 wherein each R14, R15, R18 and R19 is H.
    • Embodiment 74. A compound of Formula 1 or any one of Embodiments 1 through 73 wherein R20 is H, C1-C6 alkyl, C2-C6 alkenyl or C3-C8 cycloalkyl.
    • Embodiment 75. A compound of Embodiment 74 wherein R20 is H or CH3.
    • Embodiment 76. A compound of Formula 1 or any one of Embodiments 1 through 4, 6, 10, 11 and 14 through 51 wherein T is —CH2CH2— or —CH═CH—.
    • Embodiment 77. A compound of Embodiment 76 wherein T is —CH2CH2—.
    • Embodiment 78. A compound of Formula 1 or any one of Embodiments 1 through 17 wherein each G is independently a 5- or 6-membered heterocyclic ring optionally substituted with up to five substituents selected from R21 on carbon ring members and R22 on nitrogen ring members.
    • Embodiment 79. A compound of Embodiment 78 wherein G is




embedded image


embedded image






      • r is 0, 1, 2 or 3.



    • Embodiment 80. A compound of Embodiment 79 wherein G is G-2, G-3, G-9, G-15, G-18, G-19 or G-20.

    • Embodiment 81. A compound of Embodiment 79 wherein when R1 is G, then G is G-18, G-19 or G-20.

    • Embodiment 82. A compound of Embodiment 81 wherein when R1 is G, then G is G-19 or G-20.

    • Embodiment 83. A compound of Embodiment 82 wherein when R1 is G, then G is G-20.

    • Embodiment 84. A compound of Embodiment 82 wherein when R1 is G, then G is G-19.

    • Embodiment 85. A compound of Embodiment 79 wherein when R2 is G, then G is G-2, G-3 or G-15.

    • Embodiment 86. A compound of Embodiment 84 wherein when R2 is G, then G is G-2 or G-3.

    • Embodiment 87. A compound of Embodiment 84 wherein when R2 is G, then G is G-2.

    • Embodiment 88. A compound of Embodiment 84 wherein when R2 is G, then G is G-3.

    • Embodiment 89. A compound of Formula 1 or any one of Embodiments 1 through 88 wherein each R21 is independently halogen, cyano, hydroxy, nitro, —CHO, —SH, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C4-C10 alkylcycloalkyl, C4-C10 cycloalkylalkyl, C3-C8 cycloalkenyl, C3-C8 halocycloalkenyl, C2-C8 alkoxyalkyl, C4-C10 cycloalkoxyalkyl, C3-C10 alkoxyalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkoxyhaloalkyl, C2-C5 cyanoalkyl, C1-C6 hydroxyalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C8 cycloalkoxy, C3-C8 halocycloalkoxy, C4-C10 cycloalkylalkoxy, C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, C2-C8 alkoxyalkoxy, C2-C8 alkylcarbonyloxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3-C8 cycloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl or C3-C8 cycloalkylsulfonyl.

    • Embodiment 90. A compound of Embodiment 91 wherein each R21 is independently halogen, nitro, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy or C1-C6 alkylthio.

    • Embodiment 91. A compound of Embodiment 92 wherein each R21 is independently fluorine, chlorine, bromine, CH3, CF3, OCH3, OCF3 or SCH3.

    • Embodiment 92. A compound of Formula 1 or any one of Embodiments 1 through 91 wherein each R22 is independently C1-C6 alkyl or C1-C6 haloalkyl.

    • Embodiment 93. A compound of Embodiment 92 wherein each R22 is independently CH3 or CH2CF3.





This invention also includes a herbicidal mixture comprising (a) a compound of Formula 1 and (b) at least one additional active ingredient selected from (b1) photosystem II inhibitors, (b2) AHAS inhibitors, (b3) ACCase inhibitors, (b4) auxin mimics and (b5) EPSP inhibitors.

    • Embodiment 94. A herbicidal mixture comprising (a) a compound of Formula 1 and (b) at least one additional active ingredient selected from (b1), (b2) and (b3).
    • Embodiment 95. A herbicidal mixture comprising (a) a compound of Formula 1 and (b) at least one additional active ingredient selected from (b1).
    • Embodiment 96. A herbicidal mixture of Embodiment 95 comprising (a) a compound of Formula 1 and (b) one additional active ingredient selected from the group consisting of ametryn, amicarbazone, atrazine, bentazon, bromacil, bromoxynil, chlorotoluron, dimethametryn, diuron, hexazinone, isoproturon, metribuzin, pyridate, simazine and terbutryn.
    • Embodiment 97. A herbicidal mixture of Embodiment 95 comprising (a) a compound of Formula 1; and (b) bromoxynil.
    • Embodiment 98. A herbicidal mixture of Embodiment 95 comprising (a) a compound of Formula 1; and (b) dimethametryn.
    • Embodiment 99. A herbicidal mixture comprising (a) a compound of Formula 1 and (b) diuron and hexazinone.


Combinations of Embodiments 1-93 are illustrated by:


Embodiment A. A compound of Formula 1 wherein

    • A is A-1, A-3, A-4, A-5 or A-6;
    • R1 is phenyl, phenylsulfonyl, —W1(phenyl), —W1(S-phenyl), —W1(SO2-phenyl), —W2(SO2CH2-phenyl) or —W2(SCH2-phenyl), each optionally substituted on ring members with up to five substituents selected from R21; or -G or —W2G; or cyano, hydroxy, amino, —C(═O)OH, —C(═O)NHCN, —C(═O)NHOH, —SO2NH2, —SO2NHCN, —SO2NHOH, —NHCHO, C1-C10 alkyl, C2-C10 alkenyl, C2-C10 alkynyl, haloalkyl, C2-C10 haloalkenyl, C2-C12 haloalkynyl, C3-C12 cycloalkyl, C3-C12 halocycloalkyl, C4-C14 alkylcycloalkyl, C4-C14 cycloalkylalkyl, C6-C18 cycloalkylcycloalkyl, C4-C14 halocycloalkylalkyl, C5-C16 alkylcycloalkylalkyl, C3-C12 cycloalkenyl, C3-C12 halocycloalkenyl, C2-C12 alkoxyalkyl, C3-C12 alkoxyalkenyl, C4-C14 alkylcycloalkyl, C4-C14 alkoxycycloalkyl, C4-C14 cycloalkoxyalkyl, C5-C14 cycloalkoxyalkoxyalkyl, C3-C14 alkoxyalkoxyalkyl, C2-C12 alkylthioalkyl, C2-C12 alkylsulfinylalkyl, C2-C12 alkylsulfonylalkyl, C2-C12 alkylaminoalkyl, C3-C14 dialkylaminoalkyl, C2-C12 haloalkylaminoalkyl, C4-C14 cycloalkylaminoalkyl, C2-C12 alkylcarbonyl, C2-C12 haloalkylcarbonyl, C4-C14 cycloalkylcarbonyl, C2-C12 alkoxycarbonyl, C4-C16 cycloalkoxycarbonyl, C5-C14 cycloalkylalkoxycarbonyl, C2-C12 alkylaminocarbonyl, C3-C14 dialkylaminocarbonyl, C4-C14 cycloalkylaminocarbonyl, C2-C9 cyanoalkyl, C1-C10 hydroxyalkyl, C4-C14 cycloalkenylalkyl, C2-C12 haloalkoxyalkyl, C2-C12 alkoxyhaloalkyl, C2-C12 haloalkoxyhaloalkyl, C4-C14 halocycloalkoxyalkyl, C4-C14 cycloalkenyloxyalkyl, C4-C14 halocycloalkenyloxyalkyl, C3-C14 dialkoxyalkyl, C3-C14 alkoxyalkylcarbonyl, C3-C14 alkoxycarbonylalkyl or C2-C12 haloalkoxycarbonyl;
    • W1 is C1-C6 alkylene;
    • W2 is —CH2—;
    • R2 is phenyl or —W3(phenyl), each optionally substituted on ring members with up to five substituents selected from R21; or -G; C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C4-C10 alkylcycloalkyl, C4-C10 cycloalkylalkyl, C6-C14 cycloalkylcycloalkyl, C4-C10 halocycloalkylalkyl, C5-C12 alkylcycloalkylalkyl, C3-C8 cycloalkenyl, C3-C8 halocycloalkenyl, C2-C8 alkoxyalkyl, C3-C10 alkoxyalkenyl, C4-C10 cycloalkoxyalkyl, C4-C10 cycloalkoxylalkoxyalkyl, C3-C10 alkoxyalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylcarbonyl, C4-C10 cycloalkenylalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkoxyhaloalkyl, C2-C8 haloalkoxyhaloalkyl, C4-C10 halocycloalkoxyalkyl, C4-C10 cycloalkenyloxyalkyl, C4-C10 halocycloalkenyloxyalkyl, C3-C10 dialkoxyalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C8 cycloalkoxy, C3-C8 halocycloalkoxy, C4-C10 cycloalkylalkoxy, C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, C2-C6 alkynyloxy, C3-C6 haloalkynyloxy, C2-C8 alkoxyalkoxy, C2-C8 alkylcarbonyloxy, C2-C8 haloalkylcarbonyloxy, C4-C10 cycloalkylcarbonyloxy, C3-C10 alkylcarbonylalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3-C8 cycloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C3-C8 trialkylsilyl, C3-C8 cycloalkenyloxy, C3-C8 halocycloalkenyloxy, C2-C8 haloalkoxyalkoxy, C2-C8 alkoxyhaloalkoxy, C2-C8 haloalkoxyhaloalkoxy, C3-C10 alkoxycarbonylalkoxy, C2-C8 alkyl(thiocarbonyl)oxy, C3-C8 cycloalkylsulfinyl or C3-C10 halotrialkylsilyl;
    • W3 is —CH2—;
    • W4 is —CH2—;
    • R1 and R2 are taken together along with the atoms to which they are attached to make a 6- or 7-membered unsaturated, partially unsaturated or fully unsaturated ring along with members consisting of up to 2 oxygen atoms, 2 nitrogen atoms or 2 sulfur atoms or up to two —S(O)—, —S(O)2—, —C(O)— groups optionally substituted on carbon atom ring members selected from halogen, cyano, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C3-C8 cycloalkyl and C2-C8 alkoxyalkyl; and phenyl optionally substituted with up to 5 substituents selected from cyano, nitro, halogen, C1-C6 alkyl, C1-C6 alkoxy and C1-C6 haloalkoxy; and optionally substituted on nitrogen ring members selected from H and C1-C6 alkyl; and phenyl optionally substituted with up to 5 substituents selected from cyano, nitro, halogen, C1-C6 alkyl, C1-C6 alkoxy and C1-C6 haloalkoxy;
    • R3 is hydroxy, —O−M+, C2-C8 alkylcarbonyloxy, C2-C8 haloalkylcarbonyloxy, C4-C10 cycloalkylcarbonyloxy or C3-C10 alkylcarbonylalkoxy; or benzyloxy, phenyloxy, benzylcarbonyloxy, phenylcarbonyloxy, phenylsulfonyloxy or benzylsulfonyloxy, each optionally substituted on ring members with up to two substituents selected from R21;
    • M+ is a sodium or potassium metal cation;
    • R9 is C1-C6 alkyl;
    • R10 is H, halogen or C1-C6 alkyl;
    • R11 is H or C1-C6 alkyl;
    • R12 is H, halogen, cyano, hydroxy, amino or C1-C6 alkyl;
    • R13 is cyano or nitro;
    • each R14, R15, R18 and R19 is H or CH3;
    • R14 and R18 are taken together as —CH2CH2CH2— or —CH═CHCH2—;
    • R20 is H or CH3;
    • T is —CH2CH2— or —CH═CH—;
    • each G is G-1 through G-20 (as depicted in Embodiment 79);
    • r is 0, 1, 2 or 3;
    • each R21 is independently halogen, cyano, hydroxy, nitro, —CHO, —SH, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C4-C10 alkylcycloalkyl, C4-C10 cycloalkylalkyl, C3-C8 cycloalkenyl, C3-C8 halocycloalkenyl, C2-C8 alkoxyalkyl, C4-C10 cycloalkoxyalkyl, C3-C10 alkoxyalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkoxyhaloalkyl, C2-C5 cyanoalkyl, C1-C6 hydroxyalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C8 cycloalkoxy, C3-C8 halocycloalkoxy, C4-C10 cycloalkylalkoxy, C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, C2-C8 alkoxyalkoxy, C2-C8 alkylcarbonyloxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3-C8 cycloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl or C3-C8 cycloalkylsulfonyl; and
    • each R22 is independently C1-C6 alkyl or C1-C6 haloalkyl.


Embodiment B. A compound of Embodiment A wherein

    • X is CH;
    • A is A-3 or A-5;
    • B2 is C-3;
    • R1 is phenyl, —W1(phenyl), —W1(S-phenyl), —W1(SO2-phenyl), —W2(SO2CH2-phenyl) or —W2(SCH2-phenyl), each optionally substituted on ring members with up to five substituents selected from R21; or -G or —W2G; or C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C3-C8 cycloalkyl, C4-C10 cycloalkylalkyl, C5-C12 alkylcycloalkylalkyl, C3-C8 cycloalkenyl, C3-C8 halocycloalkenyl, C2-C8 alkoxyalkyl, C3-C10 alkoxyalkoxyalkyl, C2-C8 alkylthioalkyl or C2-C8 alkylsulfonylalkyl;
    • R2 is phenyl or —W3(phenyl), each optionally substituted on ring members with up to two substituents selected from R21; or C1-C6 alkyl, C1-C6 haloalkyl, C3-C8 cycloalkyl, C1-C6 alkoxy, C1-C6 alkylthio or C1-C6 alkylsulfonyl;
    • R3 is hydroxy or —O−M+; or phenylsulfonyloxy optionally substituted on ring members with up to two substituents selected from R21;
    • R9 is CH2CH3;
    • R10 is H or CH3;
    • W1 is —CH2—;
    • W3 is —CH2—;
    • G is G-13, G-14, G-15, G-16 or G-17; and
    • each R21 is independently halogen, nitro, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy or C1-C6 alkylthio.


Embodiment C. A compound of Embodiment A wherein

    • A is A-1, A-3 or A-5;
    • B1 is C-1;
    • B2 is C-3;
    • B3 is C-1;
    • R1 is phenyl, —W1(phenyl), —W1(S-phenyl), —W1(SO2-phenyl), —W2(SO2CH2-phenyl) or —W2(SCH2-phenyl), each optionally substituted on ring members with up to five substituents selected from R21; or -G or —W2G; or C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C3-C8 cycloalkyl, C4-C10 cycloalkylalkyl, C5-C12 alkylcycloalkylalkyl, C3-C8 cycloalkenyl, C3-C8 halocycloalkenyl, C2-C8 alkoxyalkyl, C3-C10 alkoxyalkenyl, C4-C10 alkylcycloalkyl, C4-C10 alkoxycycloalkyl, C3-C10 alkoxyalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C12 alkylsulfonylalkyl or C2-C8 alkylsulfonylalkyl;
    • W1 is —CH2—;
    • R2 is phenyl or —W3(phenyl), each optionally substituted on ring members with up to two substituents selected from R21; or -G or; or C1-C6 alkyl or C3-C8 cycloalkyl;
    • R1 and R2 are taken together along with the atoms to which they are attached to make an unsubstituted 7-membered partially unsaturated ring;
    • R3 is hydroxy or C2-C8 alkylcarbonyloxy;
    • R9 is CH2CH3;
    • R10 is H or CH3;
    • G is G-2, G-3, G-9, G-15, G-18, G-19 or G-20; and
    • R21 is independently halogen, nitro, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy or C1-C6 alkylthio.


Embodiment D. A compound of Embodiment C wherein

    • A is A-1 or A-3;
    • R1 is phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 4-methylphenyl, 4-ethylphenyl, 2-methylphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 3,5-dimethylphenyl, 3,4-dimethoxyphenyl, 2,3-dimethylphenyl, 3-fluoro-2-methylphenyl, 4-fluoro-3-methylphenyl or 5-chloro-2-methylphenyl;
    • R2 is phenyl, 2-methylphenyl, 3-methylphenyl, 3-bromophenyl, 3-chlorophenyl, 4-chlorophenyl, 3-fluorophenyl or 3,5-difluorophenyl;
    • R3 is hydroxy or —OC(═O)CH2CH(CH3)2;
    • each R14, R15, R18 and R19 is H or CH3; and
    • T is —CH2CH2—.


Embodiment E. A compound of Embodiment D wherein

    • A is A-1;
    • R1 is phenyl, 4-ethylphenyl, 4-methoxyphenyl, 3,5-dimethylphenyl, 3,4-dimethoxyphenyl, 3-fluoro-2-methylphenyl, 4-fluoro-3-methylphenyl or 5-chloro-2-methylphenyl;
    • R2 is phenyl, 3-chlorophenyl, or 2-methylphenyl;
    • R3 is hydroxy or —OC(═O)CH2CH(CH3)2; and
    • each R14, R15, R18 and R19 is H.


Embodiment F. A compound of Embodiment C wherein

    • A is A-3;
    • R1 is n-Pr or —CH2CH2OCH3;
    • R2 is phenyl, 2-methylphenyl, 3-methylphenyl, 4-chlorophenyl, 3-fluorophenyl or 3,5-difluorophenyl;
    • R3 is hydroxy; and
    • each R14, R15, R18 and R19 is H.


Embodiment G. A compound of Embodiment C wherein

    • A is A-1;
    • R1 is -G or —W2G; C1-C6 alkyl, C3-C8 cycloalkyl, or C2-C8 alkoxyalkyl;
    • G is G-19 or G-20;
    • R2 is phenyl, 2-methylphenyl, 3-methylphenyl, 4-chlorophenyl, 3-fluorophenyl or 3,5-difluorophenyl;
    • R3 is hydroxy; and
    • each R14, R15, R18 and R19 is H.


Embodiment H. A compound of Embodiment C wherein

    • A is A-1;
    • R1 is n-Pr, c-hexyl, —CH2CH2OCH3 or —CH2CH2CH2OCH3;
    • R2 is 3-thienyl or 2-thienyl;
    • R3 is hydroxy; and
    • each R14, R15, R18 and R19 is H.


Specific embodiments include a compound of Formula 1 selected from:

  • 5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2,3-diphenyl-4(3H)-pyrimidinone (Compound 2),
  • 5-[(2-hydroxy-6-oxo-1-cyclohexane-1-yl)carbonyl]-3-(3-methoxypropyl)-2-(3-methylphenyl)-4(3H)-pyrimidinone (Compound 118),
  • 5-[2-hydroxy-6-oxo-cyclohexen-1-yl)carbonyl]-3-(2-methoxyethyl)-2-(3-thienyl)-4(3H)-pyrimidinone (Compound 97),
  • 5-[2-hydroxy-6-oxo-cyclohexen-1-yl)carbonyl]-3-(4-methoxyphenyl)-2-phenyl-4(3H)-pyrimidinone (Compound 4),
  • 5-[2-hydroxy-6-oxo-cyclohexen-1-yl)carbonyl]-3-(3-methoxypropyl)-2-phenyl-4(3H)-pyrimidinone (Compound 81) and
  • 3-cyclohexyl-5-[(2-hydroxy-6-oxo-cyclohexen-1-yl)carbonyl]-2-phenyl-4(3H)-pyrimidinone (Compound 128).


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

    • Embodiment 1Q. A compound of Formula 1Q wherein A′ is A′-1, A′-3 or A′-5.
    • Embodiment 2Q. A compound of Embodiment 2Q wherein A′ is A′-1 or A′-3.
    • Embodiment 3Q. A compound of Embodiment 3Q wherein A′ is A′-1.
    • Embodiment 4Q. A compound of Embodiment 4Q wherein A′ is A′-3.
    • Embodiment 5Q. A compound of Formula 1Q or any one of Embodiments 1Q through 4Q wherein B1 is C-1.
    • Embodiment 6Q. A compound of Formula 1Q or any one of Embodiments 1Q through 4Q wherein B1 is C-2.
    • Embodiment 7Q. A compound of Formula 1Q or any one of Embodiments 1Q through 6Q wherein B2 is C-3.
    • Embodiment 8Q. A compound of Formula 1Q or any one of Embodiments 1Q through 9Q wherein B2 is C-4.
    • Embodiment 9Q. A compound of Formula 1Q or any one of Embodiments 1Q through 8Q wherein B3 is C-1.
    • Embodiment 10Q. A compound of Formula 1Q or any one of Embodiments 1Q through 8Q wherein B3 is C-2.
    • Embodiment 11Q. A compound of Formula 1Q or any one of Embodiments 1Q through 10Q wherein R1 is phenyl, —W1(phenyl), —W1(S-phenyl), —W1(SO2-phenyl), —W2(SO2CH2-phenyl) or —W2(SCH2-phenyl), each optionally substituted on ring members with up to five substituents selected from R21; or -G or —W2G; or C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C3-C8 cycloalkyl, C4-C10 cycloalkylalkyl, C5-C12 alkylcycloalkylalkyl, C3-C8 cycloalkenyl, C3-C8 halocycloalkenyl, C2-C8 alkoxyalkyl, C3-C10 alkoxyalkenyl, C4-C10 alkylcycloalkyl, C4-C10 alkoxycycloalkyl, C3-C10 alkoxyalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C12 alkylsulfinylalkyl or C2-C8 alkylsulfonylalkyl.
    • Embodiment 12Q. A compound of Embodiment 11Q wherein R1 is phenyl or —W1(phenyl), each optionally substituted on ring members with up to two substituents selected from R21; or -G or —W2G; or C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C3-C8 cycloalkyl, C4-C10 cycloalkylalkyl, C5-C12 alkylcycloalkylalkyl, C3-C8 cycloalkenyl, C3-C8 halocycloalkenyl, C2-C8 alkoxyalkyl C3-C10 alkoxyalkenyl, C4-C10 alkylcycloalkyl or C4-C10 alkoxycycloalkyl.
    • Embodiment 13Q. A compound of Embodiment 12Q wherein R1 is phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 4-methylphenyl, 4-ethylphenyl, 2-methylphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 3,5-dimethylphenyl, 3,4-dimethoxyphenyl, 2,3-dimethylphenyl, 3-fluoro-2-methylphenyl, 4-fluoro-3-methylphenyl or 5-chloro-2-methylphenyl.
    • Embodiment 14Q. A compound of Embodiment 13Q wherein R1 is phenyl, 4-ethylphenyl, 4-methoxyphenyl, 3,5-dimethylphenyl, 3,4-dimethoxyphenyl, 3-fluoro-2-methylphenyl, 4-fluoro-3-methylphenyl or 5-chloro-2-methylphenyl. Embodiment 15Q. A compound of Embodiment 14Q wherein R1 is phenyl, 3,4-dimethoxyphenyl or 5-chloro-2-methylphenyl.
    • Embodiment 16Q. A compound of Embodiment 15Q wherein R1 is phenyl.
    • Embodiment 17Q. A compound of Embodiment 14Q wherein R1 is 3,4-dimethoxyphenyl.
    • Embodiment 18Q. A compound of Embodiment 14Q wherein R1 is 5-chloro-2-methylphenyl.
    • Embodiment 19Q. A compound of Formula 1Q or any one of Embodiments 1 through 16Q wherein R1 is other than phenyl.
    • Embodiment 20Q. A compound of Embodiment 11Q wherein R1 is -G or —W2G; C1-C6 alkyl, C3-C8 cycloalkyl, or C2-C8 alkoxyalkyl.
    • Embodiment 21Q. A compound of Embodiment 20Q wherein R1 is -G or —W2G.
    • Embodiment 22Q. A compound of Embodiment 20Q wherein R1 is C1-C6 alkyl, C3-C8 cycloalkyl or C2-C8 alkoxyalkyl.
    • Embodiment 23Q. A compound of Embodiment 22Q wherein R1 is n-Pr, i-Pr, n-Bu, c-hexyl, —CH2CH2OCH3, —CH2CH2CH2OCH3 or —CH2CH2OCH2CH3.
    • Embodiment 24Q. A compound of Embodiment 23Q wherein R1 is n-Pr, c-hexyl, —CH2CH2OCH3 or —CH2CH2CH2OCH3.
    • Embodiment 25Q. A compound of Formula 1Q or any one of Embodiments 1Q through 12Q wherein W1 is C1-C6 alkylene.
    • Embodiment 26Q. A compound of Embodiment 25Q wherein W1 is —CH2—.
    • Embodiment 27Q. A compound of Formula 1Q or any one of Embodiments 1Q through 12Q, 20Q or 21Q wherein W2 is —CH2—.
    • Embodiment 28Q. A compound of Formula 1Q or any one of Embodiments Embodiment 1Q through 27Q wherein R2 is phenyl or —W3(phenyl), each optionally substituted on ring members with up to two substituents selected from R21; or -G or; or C1-C6 alkyl or C3-C8 cycloalkyl.
    • Embodiment 29Q. A compound of Embodiment 28Q wherein R2 is phenyl optionally substituted on ring members with up to two substituents selected from R21; or -G; or C1-C6 alkyl, C3-C8 cycloalkyl.
    • Embodiment 30Q. A compound of Embodiment 29Q wherein R2 is phenyl, 2-methylphenyl, 3-methylphenyl, 3-bromophenyl, 3-chlorophenyl, 4-chlorophenyl, 3-fluorophenyl or 3,5-difluorophenyl.
    • Embodiment 31Q. A compound of Embodiment 30Q wherein R2 is phenyl.
    • Embodiment 32Q. A compound of Formula 1Q or any one of Embodiments 1Q through 30Q wherein R2 is other than phenyl.
    • Embodiment 33Q. A compound of Embodiment 32Q wherein R2 is 3-thienyl or 2-thienyl.
    • Embodiment 34Q. A compound of Embodiment 33Q wherein R2 is n-propyl, n-butyl, or cyclopropyl.
    • Embodiment 35Q. A compound of Formula 1Q or any one of Embodiments 1Q through 28Q wherein W3 is —CH2—.
    • Embodiment 36Q. A compound of Formula 1Q or any one of Embodiments 1Q through 3Q, 7Q and 14Q through 51Q wherein R9 is C1-C6 alkyl.
    • Embodiment 37Q. A compound of Formula 1Q or any one of Embodiments 1Q or 11Q through 36Q wherein R9 is CH2CH3.
    • Embodiment 38Q. A compound of Formula 1Q or any one of Embodiments 1Q or 11Q through 36Q wherein R10 is H, halogen or C1-C6 alkyl.
    • Embodiment 39Q. A compound of Embodiment 38Q wherein R10 is H or CH3.
    • Embodiment 40Q. A compound of Formula 1Q or any one of Embodiments 1Q through 39Q wherein when instances of R14 and R18 are taken alone (i.e. R14 and R18 are not taken together as alkylene or alkenylene), then independently said instances of R14 and R18 are H or C1-C6 alkyl.
    • Embodiment 41Q. A compound of Embodiment 40Q wherein when instances of R14 and R18 are taken alone, then independently said instances of R14 and R18 are H or CH3.
    • Embodiment 42Q. A compound of Embodiment 41Q wherein when instances of R14 and R18 are taken alone, then independently said instances of R14 and R18 are H.
    • Embodiment 43Q. A compound of Formula 1Q or any one of Embodiments 1Q through 42Q wherein independently each R15 and R19 is H or CH3.
    • Embodiment 44Q. A compound of Embodiment 43Q wherein independently each R15 and R19 is H.
    • Embodiment 45Q. A compound of Formula 1Q or any one of Embodiments 1Q through 44Q wherein R20 is H, C1-C6 alkyl, C2-C6 alkenyl or C3-C8 cycloalkyl.
    • Embodiment 46Q. A compound of Embodiment 45Q wherein R20 is H or CH3.
    • Embodiment 47Q. A compound of Formula 1Q or any one of Embodiments 1Q, 2Q, 4Q, 7Q, 8Q and 11Q through 46Q wherein T is —CH2CH2— or —CH═CH—.
    • Embodiment 48Q. A compound of Embodiment 47Q wherein T is —CH2CH2—.
    • Embodiment 49Q. A compound of Formula 1Q or any one of Embodiments 1Q through 48Q wherein G is G-2, G-3, G-9, G-15, G-18, G-19 or G-20 (as depicted in Embodiment 79).
    • Embodiment 50Q. A compound of Embodiment 49Q wherein when R1 is G, then G is G-19 or G-20.
    • Embodiment 51Q. A compound of Embodiment 50Q wherein when R1 is G, then G is G-19.
    • Embodiment 52Q. A compound of Embodiment 50Q wherein when R1 is G, then G is G-20.
    • Embodiment 53Q. A compound of Embodiment 49Q wherein when R2 is G, then G is G-2, G-3 or G-15.
    • Embodiment 54Q. A compound of Embodiment 53Q wherein when R2 is G, then G is G-2.
    • Embodiment 55Q. A compound of Embodiment 53Q wherein when R2 is G, then G is G-3.
    • Embodiment 56Q. A compound of Formula 1Q or any one of Embodiments 1Q through 55Q wherein each R21 is independently halogen, nitro, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy or C1-C6 alkylthio.
    • Embodiment 57Q. A compound of Embodiment 56Q wherein each R21 is independently fluorine, chlorine, bromine, CH3, CF3, OCH3, OCF3 or SCH3.
    • Embodiment 58Q. A compound of Formula 1Q or any one of Embodiments 1Q through 57Q wherein each R22 is independently C1-C6 alkyl or C1-C6 haloalkyl.
    • Embodiment 59Q. A compound of Embodiment 58Q wherein each R22 is independently CH3 or CH2CF3.


Embodiments of the present invention as described in the Summary of the Invention also include (where Formula 1R from the Summary of the Invention as used in the following Embodiments include N-oxides and salts thereof):

    • Embodiment 1R. A compound of Formula 1R wherein R1 is phenyl, —W1(phenyl), —W1(S-phenyl), —W1(SO2-phenyl), —W2(SO2CH2-phenyl) or —W2(SCH2-phenyl), each optionally substituted on ring members with up to five substituents selected from R21; or -G or —W2G; or C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C3-C8 cycloalkyl, C4-C10 cycloalkylalkyl, C5-C12 alkylcycloalkylalkyl, C3-C8 cycloalkenyl, C3-C8 halocycloalkenyl, C2-C8 alkoxyalkyl, C3-C10 alkoxyalkenyl, C4-C10 alkylcycloalkyl, C4-C10 alkoxycycloalkyl, C3-C10 alkoxyalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C12 alkylsulfinylalkyl or C2-C8 alkylsulfonylalkyl.
    • Embodiment 2R. A compound of Embodiment 1R wherein R1 is phenyl or —W1(phenyl), each optionally substituted on ring members with up to two substituents selected from R21; or -G or —W2G; or C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C3-C8 cycloalkyl, C4-C10 cycloalkylalkyl, C5-C12 alkylcycloalkylalkyl, C3-C8 cycloalkenyl, C3-C8 halocycloalkenyl, C2-C8 alkoxyalkyl, C3-C10 alkoxyalkenyl, C4-C10 alkylcycloalkyl or C4-C10 alkoxycycloalkyl.
    • Embodiment 3R. A compound of Embodiment 2R wherein R1 is phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 4-methylphenyl, 4-ethylphenyl, 2-methylphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 3,5-dimethylphenyl, 3,4-dimethoxyphenyl, 2,3-dimethylphenyl, 3-fluoro-2-methylphenyl, 4-fluoro-3-methylphenyl or 5-chloro-2-methylphenyl.
    • Embodiment 4R. A compound of Embodiment 3R wherein R1 is phenyl, 4-ethylphenyl, 4-methoxyphenyl, 3,5-dimethylphenyl, 3,4-dimethoxyphenyl, 3-fluoro-2-methylphenyl, 4-fluoro-3-methylphenyl or 5-chloro-2-methylphenyl.
    • Embodiment 5R. A compound of Embodiment 4R wherein R1 is phenyl, 3,4-dimethoxyphenyl or 5-chloro-2-methylphenyl.
    • Embodiment 6R. A compound of Embodiment 5R wherein R1 is phenyl.
    • Embodiment 7R. A compound of Embodiment 4R wherein R1 is 3,4-dimethoxyphenyl.
    • Embodiment 8R. A compound of Embodiment 4R wherein R1 is 5-chloro-2-methylphenyl.
    • Embodiment 9R. A compound of Formula 1R or any one of Embodiments 1R through 8R wherein R1 is other than phenyl.
    • Embodiment 10R. A compound of Formula 1R or any one of Embodiments 1R and 2R R wherein R1 is -G or —W2G; C1-C6 alkyl, C3-C8 cycloalkyl, or C2-C8 alkoxyalkyl.
    • Embodiment 11R. A compound of Embodiment 10R wherein R1 is -G or —W2G.
    • Embodiment 12R. A compound of Embodiment 10R wherein R1 is C1-C6 alkyl, C3-C8 cycloalkyl, or C2-C8 alkoxyalkyl.
    • Embodiment 13R. A compound of Embodiment 12R wherein R1 is n-Pr, i-Pr, n-Bu, c-hexyl, —CH2CH2OCH3, —CH2CH2CH2OCH3 or —CH2CH2OCH2CH3.
    • Embodiment 14R. A compound of Embodiment 13R wherein R1 is n-Pr, c-hexyl, —CH2CH2OCH3 or —CH2CH2CH2OCH3.
    • Embodiment 15R. A compound of Formula 1R or any one of Embodiments 1R and 2R wherein W1 is C1-C6 alkylene.
    • Embodiment 16R. A compound of Embodiment 15R wherein W1 is —CH2—.
    • Embodiment 17R. A compound of Formula 1R or any one of Embodiments 1R, 2R 10R and 11R wherein W2 is —CH2—.
    • Embodiment 18R. A compound of Formula 1R or any one of Embodiments Embodiment 1R through 17R wherein R2 is phenyl or —W3(phenyl), each optionally substituted on ring members with up to two substituents selected from R21; or -G or; or C1-C6 alkyl or C3-C8 cycloalkyl.
    • Embodiment 19R. A compound of Embodiment 18R wherein R2 is phenyl optionally substituted on ring members with up to two substituents selected from R21; or -G; or C1-C6 alkyl or C3-C8 cycloalkyl.
    • Embodiment 20R. A compound of Embodiment 19R wherein R2 is phenyl, 2-methylphenyl, 3-methylphenyl, 3-bromophenyl, 3-chlorophenyl, 4-chlorophenyl, 3-fluorophenyl or 3,5-difluorophenyl.
    • Embodiment 21R. A compound of Embodiment 20R wherein R2 is phenyl.
    • Embodiment 22R. A compound of Formula 1R or any one of Embodiments 1R through 21R wherein R2 is other than phenyl.
    • Embodiment 23R. A compound of Embodiment 22R wherein R2 is 3-thienyl or 2-thienyl.
    • Embodiment 24R. A compound of Embodiment 23R wherein R2 is n-propyl, n-butyl, or cyclopropyl.
    • Embodiment 25R. A compound of Formula 1R or any one of Embodiments 1R through 18R wherein W3 is —CH2—.
    • Embodiment 26R. A compound of Formula 1R or any one of Embodiments 1R through 25R wherein G is G-2, G-3, G-9, G-15, G-18, G-19 or G-20 (as depicted in Embodiment 79).
    • Embodiment 27R. A compound of Embodiment 26R wherein when R1 is G, then G is G-19 or G-20.
    • Embodiment 28R. A compound of Embodiment 27R wherein when R1 is G, then G is G-19.
    • Embodiment 29R. A compound of Embodiment 28R wherein when R1 is G, then G is G-20.
    • Embodiment 30R. A compound of Embodiment 26R wherein when R2 is G, then G is G-2, G-3 or G-15.
    • Embodiment 31R. A compound of Embodiment 30R wherein when R2 is G, then G is G-2.
    • Embodiment 32R. A compound of Embodiment 31R wherein when R2 is G, then G is G-3.
    • Embodiment 33R. A compound of Formula 1R or any one of Embodiments 1R through 32R wherein each R21 is independently halogen, nitro, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy or C1-C6 alkylthio.
    • Embodiment 34R. A compound of Embodiment 33R wherein each R21 is independently fluorine, chlorine, bromine, CH3, CF3, OCH3, OCF3 or SCH3.
    • Embodiment 35R. A compound of Formula 1R or any one of Embodiments 1R through 32R wherein each R22 is independently C1-C6 alkyl or C1-C6 haloalkyl.
    • Embodiment 36R. A compound of Embodiment 35R wherein each R22 is independently CH3 or CH2CF3.


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

    • Embodiment 1S. A compound of Formula 1S wherein R1 is phenyl, —W1(phenyl), —W1(S-phenyl), —W1(SO2-phenyl), —W2(SO2CH2-phenyl) or —W2(SCH2-phenyl), each optionally substituted on ring members with up to five substituents selected from R21; or -G or —W2G; or C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C3-C8 cycloalkyl, C4-C10 cycloalkylalkyl, C5-C12 alkylcycloalkylalkyl, C3-C8 cycloalkenyl, C3-C8 halocycloalkenyl, C2-C8 alkoxyalkyl, C3-C10 alkoxyalkenyl, C4-C10 alkylcycloalkyl, C4-C10 alkoxycycloalkyl, C3-C10 alkoxyalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C12 alkylsulfinylalkyl or C2-C8 alkylsulfonylalkyl.
    • Embodiment 2S. A compound of Embodiment 1S wherein R1 is phenyl or —W1(phenyl), each optionally substituted on ring members with up to two substituents selected from R21; or -G or —W2G; or C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C3-C8 cycloalkyl, C4-C10 cycloalkylalkyl, C5-C12 alkylcycloalkylalkyl, C3-C8 cycloalkenyl, C3-C8 halocycloalkenyl, C2-C8 alkoxyalkyl, C3-C10 alkoxyalkenyl, C4-C10 alkylcycloalkyl, C4-C10 alkoxycycloalkyl.
    • Embodiment 3S. A compound of Embodiment 2S wherein R1 is phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 4-methylphenyl, 4-ethylphenyl, 2-methylphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 3,5-dimethylphenyl, 3,4-dimethoxyphenyl, 2,3-dimethylphenyl, 3-fluoro-2-methylphenyl, 4-fluoro-3-methylphenyl or 5-chloro-2-methylphenyl.
    • Embodiment 4S. A compound of Embodiment 3S wherein R1 is phenyl, 4-ethylphenyl, 4-methoxyphenyl, 3,5-dimethylphenyl, 3,4-dimethoxyphenyl, 3-fluoro-2-methylphenyl, 4-fluoro-3-methylphenyl or 5-chloro-2-methylphenyl.
    • Embodiment 5S. A compound of Embodiment 4S wherein R1 is phenyl, 3,4-dimethoxyphenyl or 5-chloro-2-methylphenyl.
    • Embodiment 6S. A compound of Embodiment 5S wherein R1 is phenyl.
    • Embodiment 7S. A compound of Embodiment 4S wherein R1 is 3,4-dimethoxyphenyl.
    • Embodiment 8S. A compound of Embodiment 4S wherein R1 is 5-chloro-2-methylphenyl.
    • Embodiment 9S. A compound of Formula 1S or any one of Embodiments 1S through 8S wherein R1 is other than phenyl.
    • Embodiment 10S. A compound of Formula 1S or any one of Embodiments 1S and 2S wherein R1 is -G or —W2G; C1-C6 alkyl, C3-C8 cycloalkyl, or C2-C8 alkoxyalkyl.
    • Embodiment 11S. A compound of Embodiment 10S wherein R1 is -G or —W2G.
    • Embodiment 12S. A compound of Embodiment 10S wherein R1 is C1-C6 alkyl, C3-C8 cycloalkyl, or C2-C8 alkoxyalkyl.
    • Embodiment 13S. A compound of Embodiment 12S wherein R1 is n-Pr, i-Pr, n-Bu, c-hexyl, —CH2CH2OCH3, —CH2CH2CH2OCH3 or —CH2CH2OCH2CH3.
    • Embodiment 14S. A compound of Embodiment 13S wherein R1 is n-Pr, c-hexyl, —CH2CH2OCH3 or —CH2CH2CH2OCH3.
    • Embodiment 15S. A compound of Formula 1S or any one of Embodiments 1S and 2S wherein W1 is C1-C6 alkylene.
    • Embodiment 16S. A compound of Embodiment 15S wherein W1 is —CH2—.
    • Embodiment 17S. A compound of Formula 15 or any one of Embodiments 1S, 2S 10S and 11S wherein W2 is —CH2—.
    • Embodiment 18S. A compound of Formula 1s or any one of Embodiments Embodiment 1S through 17S wherein R2 is phenyl or —W3(phenyl), each optionally substituted on ring members with up to two substituents selected from R21; or -G or; or C1-C6 alkyl or C3-C8 cycloalkyl.
    • Embodiment 19S. A compound of Embodiment 18S wherein R2 is phenyl optionally substituted on ring members with up to two substituents selected from R21; or -G; or C1-C6 alkyl, C3-C8 cycloalkyl.
    • Embodiment 20S. A compound of Embodiment 19S wherein R2 is phenyl, 2-methylphenyl, 3-methylphenyl, 3-bromophenyl, 3-chlorophenyl, 4-chlorophenyl, 3-fluorophenyl or 3,5-difluorophenyl.
    • Embodiment 21S. A compound of Embodiment 20S wherein R2 is phenyl.
    • Embodiment 22S. A compound of Formula 1S or any one of Embodiments 1S through 21S wherein R2 is other than phenyl.
    • Embodiment 23S. A compound of Embodiment 22S wherein R2 is 3-thienyl or 2-thienyl.
    • Embodiment 24S. A compound of Embodiment 23S wherein R2 is n-propyl, n-butyl, or cyclopropyl.
    • Embodiment 25S. A compound of Formula 1S or any one of Embodiments 1S through 18S wherein W3 is —CH2—.
    • Embodiment 26S. A compound of Formula 1S or any one of Embodiments 1S through 25S wherein G is G-2, G-3, G-9, G-15, G-18, G-19 or G-20 (as depicted in Embodiment 79).
    • Embodiment 27S. A compound of Embodiment 26S wherein when R1 is G, then G is G-19 or G-20.
    • Embodiment 28S. A compound of Embodiment 27S wherein when R1 is G, then G is G-19.
    • Embodiment 29S. A compound of Embodiment 28S wherein when R1 is G, then G is G-20.
    • Embodiment 30S. A compound of Embodiment 26S wherein when R2 is G, then G is G-2, G-3 or G-15.
    • Embodiment 31S. A compound of Embodiment 30R wherein when R2 is G, then G is G-2.
    • Embodiment 32S. A compound of Embodiment 31R wherein when R2 is G, then G is G-3.
    • Embodiment 33S. A compound of Formula 1R or any one of Embodiments 1R through 32R wherein each R21 is independently halogen, nitro, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy or C1-C6 alkylthio.
    • Embodiment 34S. A compound of Embodiment 33R wherein each R21 is independently fluorine, chlorine, bromine, CH3, CF3, OCH3, OCF3 or SCH3.
    • Embodiment 35S. A compound of Formula 1R or any one of Embodiments 1R through 32R wherein each R22 is independently C1-C6 alkyl or C1-C6 haloalkyl.
    • Embodiment 36S. A compound of Embodiment 58Q wherein each R22 is independently CH3 or CH2CF3.
    • Embodiment 37S. A compound of Formula 1S or any on of Embodiments 1S through 36S wherein when R23 is an optionally substituted carbon moiety, R23 is C1-C16 alkyl; or phenyl or benzyl optionally substituted with halogen, nitro, cyano or hydroxy on ring members.
    • Embodiment 38S. A compound of Embodiment 37S wherein when R23 is an optionally substituted carbon moiety, R23 is C1-C10 alkyl; or phenyl or benzyl optionally substituted with halogen or nitro on ring members.
    • Embodiment 39S. A compound of Embodiment 38S wherein when R23 is an optionally substituted carbon moiety, R23 is C1-C6 alkyl; or benzyl optionally substituted with halogen or nitro on ring members.
    • Embodiment 40S. A compound of Embodiment 39S wherein when R23 is an optionally substituted carbon moiety, R23 is C1-C6 alkyl; or unsubstituted benzyl.
    • Embodiment 41S. A compound of Embodiment 40S wherein when R23 is an optionally substituted carbon moiety, R23 is C1-C6 alkyl.
    • Embodiment 42S. A compound of Embodiment 41S wherein when R23 is an optionally substituted carbon moiety, R23 is unsubstituted benzyl.
    • Embodiment 43S. A compound of Embodiment 42S wherein when R23 is an optionally substituted carbon moiety, R23 is ethyl, n-propyl, n-butyl or i-propyl.
    • Embodiment 44S. A compound of Embodiment 43S wherein when R23 is an optionally substituted carbon moiety, R23 is ethyl, n-propyl or i-propyl.
    • Embodiment 45S. A compound of Embodiment 44S wherein when R23 is an optionally substituted carbon moiety, R23 is ethyl.


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

    • Embodiment P1. A compound of Formula 1P wherein X is N.
    • Embodiment P2. A compound of Formula 1P wherein X is CH.
    • Embodiment P3. A compound of Formula 1P or any one of Embodiments P1 through P2 wherein Y is C(O).
    • Embodiment P4. A compound of Formula 1P or Embodiment P2 wherein Y is S(O)2.
    • Embodiment P5. A compound of Formula 1P or any one of Embodiments P1 through P4 wherein A is A-1, A-3, A-4, A-5 or A-6.
    • Embodiment P6. A compound of Embodiment P5 wherein A is A-1, A-3, A-5 or A-6.
    • Embodiment P7. A compound of Embodiment P6 wherein A is A-3 or A-5.
    • Embodiment P8. A compound of Embodiment P7 wherein A is A-3.
    • Embodiment P9. A compound of Embodiment P6 wherein A is A-1 or A-6.
    • Embodiment P10. A compound of Embodiment P9 wherein A is A-1.
    • Embodiment P11. A compound of Formula 1P or any one of Embodiments P1 through P9 wherein A is other than A-1.
    • Embodiment P12. A compound of Formula 1P or any one of Embodiments P1 through P11 wherein B1 is C-1.
    • Embodiment P13. A compound of Formula 1P or any one of Embodiments P1 through P11 wherein B1 is C-2.
    • Embodiment P14. A compound of Formula 1P or any one of Embodiments P1 through P13 wherein B2 is C-3.
    • Embodiment P15. A compound of Formula 1P or any one of Embodiments P1 through P13 wherein B2 is C-4.
    • Embodiment P16. A compound of Formula 1P or any one of Embodiments P1 through P13 wherein B2 is C-6
    • Embodiment P17. A compound of Formula 1P or any one of Embodiments P1 through P13 wherein B2 is C-7.
    • Embodiment P18. A compound of Formula 1P or any one of Embodiments P1 through P17 wherein B3 is C-1.
    • Embodiment P19. A compound of Formula 1P or any one of Embodiments P1 through P17 wherein B3 is C-2.
    • Embodiment P20. A compound of Formula 1P or any one of Embodiments P1 through P19 wherein R1 is phenyl, phenylsulfonyl, —W1(phenyl), —W1(S-phenyl), —W1(SO2-phenyl), —W2(SO2CH2-phenyl) or —W2(SCH2-phenyl), each optionally substituted on ring members with up to five substituents selected from R21; or -G or —W2G; or cyano, hydroxy, amino, —C(═O)OH, —C(═O)NHCN, —C(═O)NHOH, —SO2NH2, —SO2NHCN, —SO2NHOH, —NHCHO, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C4-C10 alkylcycloalkyl, C4-C10 cycloalkylalkyl, C6-C14 cycloalkylcycloalkyl, C4-C10 halocycloalkylalkyl, C5-C12 alkylcycloalkylalkyl, C3-C8 cycloalkenyl, C3-C8 halocycloalkenyl, C2-C8 alkoxyalkyl, C4-C10 cycloalkoxyalkyl, C3-C10 alkoxyalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylaminoalkyl, C3-C10 dialkylaminoalkyl, C2-C8 haloalkylaminoalkyl, C4-C10 cycloalkylaminoalkyl, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C10 cycloalkylcarbonyl, C2-C8 alkoxycarbonyl, C4-C10 cycloalkoxycarbonyl, C5-C12 cycloalkylalkoxycarbonyl, C2-C8 alkylaminocarbonyl, C3-C10 dialkylaminocarbonyl, C4-C10 cycloalkylaminocarbonyl, C2-C5 cyanoalkyl, C1-C6 hydroxyalkyl, C4-C10 cycloalkenylalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkoxyhaloalkyl, C2-C8 haloalkoxyhaloalkyl, C4-C10 halocycloalkoxyalkyl, C4-C10 cycloalkenyloxyalkyl, C4-C10 halocycloalkenyloxyalkyl, C3-C10 dialkoxyalkyl, C3-C10 alkoxyalkylcarbonyl, C3-C10 alkoxycarbonylalkyl or C2-C8 haloalkoxycarbonyl.
    • Embodiment P21. A compound of Embodiment P20 wherein R1 is phenyl, —W1(phenyl), —W1(S-phenyl), —W1(SO2-phenyl), —W2(SO2CH2-phenyl) or —W2(SCH2-phenyl), each optionally substituted on ring members with up to five substituents selected from R21; or -G or —W2G; or C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C3-C8 cycloalkyl, C4-C10 cycloalkylalkyl, C5-C12 alkylcycloalkylalkyl, C3-C8 cycloalkenyl, C3-C8 halocycloalkenyl, C2-C8 alkoxyalkyl, C3-C10 alkoxyalkoxyalkyl, C2-C8 alkylthioalkyl or C2-C8 alkylsulfonylalkyl.
    • Embodiment P22. A compound of Embodiment P21 wherein R1 is phenyl or —W1(phenyl), each optionally substituted on ring members with up to two substituents selected from R21; or C1-C6 alkyl or C2-C6 alkenyl.
    • Embodiment P23. A compound of Embodiment P22 wherein R1 is phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 4-methylphenyl, 2-methylphenyl, 4-methoxyphenyl, 2,3-dimethylphenyl, CH2(phenyl), CH3 or CH2CH3.
    • Embodiment P24. A compound of Embodiment P23 wherein R1 is phenyl.
    • Embodiment P25. A compound of Formula 1P or any one of Embodiments P1 through P22 wherein W1 is C1-C6 alkylene.
    • Embodiment P26. A compound of Embodiment P25 wherein W1 is —CH2—.
    • Embodiment P27. A compound of Formula 1P or any one of Embodiments P1 through P21 or P25 or P26 wherein W2 is —CH2—.
    • Embodiment P28. A compound of Formula 1P or any one of Embodiments P1 through P27 wherein R2 is phenyl or —W3(phenyl), each optionally substituted on ring members with up to five substituents selected from R21; or C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C4-C10 alkylcycloalkyl, C4-C10 cycloalkylalkyl, C6-C14 cycloalkylcycloalkyl, C4-C10 halocycloalkylalkyl, C5-C12 alkylcycloalkylalkyl, C3-C8 cycloalkenyl, C3-C8 halocycloalkenyl, C2-C8 alkoxyalkyl, C4-C10 cycloalkoxyalkyl, C4-C10 cycloalkoxylalkoxyalkyl, C3-C10 alkoxyalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylcarbonyl, C4-C10 cycloalkenylalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkoxyhaloalkyl, C2-C8 haloalkoxyhaloalkyl, C4-C10 halocycloalkoxyalkyl, C4-C10 cycloalkenyloxyalkyl, C4-C10 halocycloalkenyloxyalkyl, C3-C10 dialkoxyalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C8 cycloalkoxy, C3-C8 halocycloalkoxy, C4-C10 cycloalkylalkoxy, C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, C2-C6 alkynyloxy, C3-C6 haloalkynyloxy, C2-C8 alkoxyalkoxy, C2-C8 alkylcarbonyloxy, C2-C8 haloalkylcarbonyloxy, C4-C10 cycloalkylcarbonyloxy, C3-C10 alkylcarbonylalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3-C8 cycloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C3-C8 trialkylsilyl, C3-C8 cycloalkenyloxy, C3-C8 halocycloalkenyloxy, C2-C8 haloalkoxyalkoxy, C2-C8 alkoxyhaloalkoxy, C2-C8 haloalkoxyhaloalkoxy, C3-C10 alkoxycarbonylalkoxy, C2-C8 alkyl(thiocarbonyl)oxy, C3-C8 cycloalkylsulfinyl or C3-C10 halotrialkylsilyl.
    • Embodiment P29. A compound of Embodiment P28 wherein R2 is phenyl or —W3(phenyl), each optionally substituted on ring members with up to two substituents selected from R21; or C1-C6 alkyl, C1-C6 haloalkyl, C3-C8 cycloalkyl, C1-C6 alkoxy, C1-C6 alkylthio or C1-C6 alkylsulfonyl.
    • Embodiment P30. A compound of Embodiment P29 wherein R2 is phenyl or CH2(phenyl), each optionally substituted on ring members with up to two substituents selected from R21; or C1-C6 alkyl, C3-C8 cycloalkyl or C1-C6 alkylthio.
    • Embodiment P31. A compound of Embodiment P30 wherein R2 is phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, CH2CH3, cyclopropyl or SCH3.
    • Embodiment P32. A compound of Formula 1P or any one of Embodiments P1 through P29 wherein W3 is C1-C6 alkylene.
    • Embodiment P33. A compound of Embodiment P32 wherein W3 is —CH2—.
    • Embodiment P34. A compound of Formula 1P or any one of Embodiments P1 through P27 or P32 or P33 wherein W4 is —CH2—.
    • Embodiment P35. A compound of Formula 1P or any one of Embodiments P1 through P34 wherein R3 is hydroxy, —O−M+, C2-C8 alkylcarbonyloxy, C2-C8 haloalkylcarbonyloxy, C4-C10 cycloalkylcarbonyloxy or C3-C10 alkylcarbonylalkoxy; or benzyloxy, phenyloxy, benzylcarbonyloxy, phenylcarbonyloxy, phenylsulfonyloxy or benzylsulfonyloxy, each optionally substituted on ring members with up to two substituents selected from R21.
    • Embodiment P36. A compound of Embodiment P35 wherein R3 is hydroxy or —O−M+; or phenylsulfonyloxy optionally substituted with up to two substituents selected from R21.
    • Embodiment P37. A compound of Embodiment P36 wherein R3 is hydroxy; or phenylsulfonyloxy substituted with CH3 at the 4-position.
    • Embodiment P38. A compound of Formula 1P or any one of Embodiments P1 through P36 wherein M+ is a sodium or potassium metal cation.
    • Embodiment P39. A compound of Formula 1P or any of Embodiments P1 through P7 and P12 through P38 wherein R4, R5, R6 and R7 are each independently H, or C1-C6 alkyl.
    • Embodiment P40. A compound of Formula 1P or any one of Embodiments P1 through P7 and 12 through 39 wherein R8 is C1-C6 alkyl or C3-C8 cycloalkyl.
    • Embodiment P41. A compound of Embodiment P40 wherein R8 is CH3, CH2CH3 or cyclopropyl.
    • Embodiment P42. A compound of Formula 1P or any one of Embodiments P1 through P9 and 12 through 41 wherein R9 is C1-C6 alkyl.
    • Embodiment P43. A compound of Embodiment P42 wherein R9 is CH2CH3.
    • Embodiment P44. A compound of Formula 1P or any one of Embodiments P1 through P9 and 12 through 41 wherein R10 is H, halogen or C1-C6 alkyl.
    • Embodiment P45. A compound of Embodiment P44 wherein R10 is H or CH3.
    • Embodiment P46. A compound of Formula 1P or any one of Embodiments P1 through P8, P10, and P12 through P45 wherein R11 is H or C1-C6 alkyl.
    • Embodiment P47. A compound of Embodiment P46 wherein R11 is H.
    • Embodiment P48. A compound of Formula 1P or any one of Embodiments P1 through P8, P10, and P12 through P47 wherein R12 is H, halogen, cyano, hydroxy, amino or C1-C6 alkyl.
    • Embodiment P49. A compound of Embodiment P48 wherein R12 is H, halogen, cyano, C1-C6 alkyl or C3-C8 cycloalkyl.
    • Embodiment P50. A compound of Embodiment P49 wherein R12 is CH3, CH2CH3 or cyclopropyl.
    • Embodiment P51. A compound of Formula 1P or any one of Embodiments P1 through P6 and P12 through P50 wherein R13 is H, halogen, cyano or nitro.
    • Embodiment P52. A compound of Embodiment P51 wherein R13 is cyano or nitro.
    • Embodiment P53. A compound of Formula 1P or any one of Embodiments P1 through P52 wherein when instances of R14 and R18 are taken alone (i.e. R14 and R18 are not taken together as alkylene or alkenylene), then independently said instances of R14 and R18 are H or C1-C6 alkyl.
    • Embodiment P53a. A compound of Embodiment P53 wherein when instances of R14 and R18 are taken alone, then independently said instances of R14 and R18 are H or CH3.
    • Embodiment P53b. A compound of Embodiment P53a wherein when instances of R14 and R18 are taken alone, then independently said instances of R14 and R18 are H.
    • Embodiment P53c. A compound of Formula 1P or any one of Embodiments P1 through P53b wherein when instances of R14 and R18 are taken together, then said instances of R14 and R18 are taken together as —CH2CH2CH2— or —CH═CH—CH2—.
    • Embodiment P53d. A compound of Formula 1P or any one of Embodiments P1 through P53b wherein all instances of R14 and R18 are taken alone.
    • Embodiment P54. A compound of Formula 1P or any one of Embodiments P1 through P53d wherein independently each R15 and R19 is H or C1-C6 alkyl.
    • Embodiment P54a. A compound of Embodiment P54 wherein independently each R15 and R19 is H or CH3.
    • Embodiment P55. A compound of Embodiment P54a wherein independently each R15 and R19 is H.
    • Embodiment P56. A compound of Formula 1P or any one of Embodiments P1 through P55 wherein R20 is H, C1-C6 alkyl, C2-C6 alkenyl or C3-C8 cycloalkyl.
    • Embodiment P57. A compound of Embodiment P56 wherein R20 is H or CH3.
    • Embodiment P58. A compound of Formula 1P or any one of Embodiments P1 through P57 wherein T is —CH2CH2— or —CH═CH—.
    • Embodiment P59. A compound of Formula 1P or any one of Embodiments P1 through P58 wherein each G is independently a 5- or 6-membered heterocyclic ring optionally substituted with up to five substituents selected from R21 on carbon ring members and R22 on nitrogen ring members.
    • Embodiment P60. A compound of Embodiment P59 wherein G is selected from




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      • r is 0, 1, 2 or 3.



    • Embodiment P61. A compound of Embodiment P60 wherein G is G-13, G-14, G-15, G-16 or G-17.

    • Embodiment P62. A compound of Formula 1P or any one of Embodiments P1 through P61 wherein each R21 is independently halogen, cyano, hydroxy, nitro, —CHO, —SH, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C4-C10 alkylcycloalkyl, C4-C10 cycloalkylalkyl, C3-C8 cycloalkenyl, C3-C8 halocycloalkenyl, C2-C8 alkoxyalkyl, C4-C10 cycloalkoxyalkyl, C3-C10 alkoxyalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkoxyhaloalkyl, C2-C5 cyanoalkyl, C1-C6 hydroxyalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C8 cycloalkoxy, C3-C8 halocycloalkoxy, C4-C10 cycloalkylalkoxy, C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, C2-C8 alkoxyalkoxy, C2-C8 alkylcarbonyloxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3-C8 cycloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl or C3-C8 cycloalkylsulfonyl.

    • Embodiment P63. A compound of Embodiment P62 wherein each R21 is independently halogen, nitro, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy or C1-C6 alkylthio.

    • Embodiment P64. A compound of Embodiment P61 wherein each R21 is independently fluorine, chlorine, CH3, CF3, OCH3, OCF3 or SCH3.

    • Embodiment P65. A compound of Formula 1P or any one of Embodiments P1 through P64 wherein each R22 is independently C1-C6 alkyl or C1-C6 haloalkyl.

    • Embodiment P66. A compound of Embodiment P1 through 65 wherein each R22 is independently CH3 or CH2CF3.





This invention also includes a herbicidal mixture of (a) a compound of Formula 1P and (b) an active ingredient selected from photosystem II inhibitors.

    • Embodiment P67. A herbicidal mixture comprising (a) a compound of Formula 1P and (b) an additional herbicidal ingredient selected from photosystem II inhibitors.
    • Embodiment P68. A herbicidal mixture of Embodiment P67 comprising (a) a compound of Formula 1P and (b) an additional herbicidal compound selected from the group consisting of ametryn, amicarbazone, atrazine, bentazon, bromacil, bromoxynil, chlorotoluron, diuron, hexazinone, isoproturon, metribuzin, pyridate, simazine and terbutryn.
    • Embodiment P69. A herbicidal mixture of Embodiment P68 comprising (a) a compound of Formula 1P; and (b) bromoxynil.


      Embodiments of this invention, including Embodiments P1-P69 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 1P but also to the starting compounds and intermediate compounds useful for preparing the compounds of Formula 1P. In addition, embodiments of this invention, including Embodiments 1-66 above as well as any other embodiments described herein, and any combination thereof, pertain to the compositions and methods of the present invention.


Combinations of Embodiments 1-66 are illustrated by:


Embodiment PA. A compound of Formula 1P wherein

    • Y is C(O);
    • A is A-1, A-3, A-5 or A-6;
    • R1 is phenyl, phenylsulfonyl, —W1(phenyl), —W1(S-phenyl), —W1(SO2-phenyl), —W2(SO2CH2-phenyl) or —W2(SCH2-phenyl), each optionally substituted on ring members with up to five substituents selected from R21; or -G or —W2G; or cyano, hydroxy, amino, —C(═O)OH, —C(═O)NHCN, —C(═O)NHOH, —SO2NH2, —SO2NHCN, —SO2NHOH, —NHCHO, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C4-C10 alkylcycloalkyl, C4-C10 cycloalkylalkyl, C6-C14 cycloalkylcycloalkyl, C4-C10 halocycloalkylalkyl, C5-C12 alkylcycloalkylalkyl, C3-C8 cycloalkenyl, C3-C8 halocycloalkenyl, C2-C8 alkoxyalkyl, C4-C10 cycloalkoxyalkyl, C3-C10 alkoxyalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylaminoalkyl, C3-C10 dialkylaminoalkyl, C2-C8 haloalkylaminoalkyl, C4-C10 cycloalkylaminoalkyl, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C10 cycloalkylcarbonyl, C2-C8 alkoxycarbonyl, C4-C10 cycloalkoxycarbonyl, C5-C12 cycloalkylalkoxycarbonyl, C2-C8 alkylaminocarbonyl, C3-C10 dialkylaminocarbonyl, C4-C10 cycloalkylaminocarbonyl, C2-C5 cyanoalkyl, C1-C6 hydroxyalkyl, C4-C10 cycloalkenylalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkoxyhaloalkyl, C2-C8 haloalkoxyhaloalkyl, C4-C10 halocycloalkoxyalkyl, C4-C10 cycloalkenyloxyalkyl, C4-C10 halocycloalkenyloxyalkyl, C3-C10 dialkoxyalkyl, C3-C10 alkoxyalkylcarbonyl, C3-C10 alkoxycarbonylalkyl or C2-C8 haloalkoxycarbonyl;
    • W1 is C1-C6 alkylene
    • W2 is —CH2—;
    • R2 is phenyl or —W3(phenyl), each optionally substituted on ring members with up to five substituents selected from R21; or C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C4-C10 alkylcycloalkyl, C4-C10 cycloalkylalkyl, C6-C14 cycloalkylcycloalkyl, C4-C10 halocycloalkylalkyl, C5-C12 alkylcycloalkylalkyl, C3-C8 cycloalkenyl, C3-C8 halocycloalkenyl, C2-C8 alkoxyalkyl, C4-C10 cycloalkoxyalkyl, C4-C10 cycloalkoxylalkoxyalkyl, C3-C10 alkoxyalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylcarbonyl, C4-C10 cycloalkenylalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkoxyhaloalkyl, C2-C8 haloalkoxyhaloalkyl, C4-C10 halocycloalkoxyalkyl, C4-C10 cycloalkenyloxyalkyl, C4-C10 halocycloalkenyloxyalkyl, C3-C10 dialkoxyalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C8 cycloalkoxy, C3-C8 halocycloalkoxy, C4-C10 cycloalkylalkoxy, C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, C2-C6 alkynyloxy, C3-C6 haloalkynyloxy, C2-C8 alkoxyalkoxy, C2-C8 alkylcarbonyloxy, C2-C8 haloalkylcarbonyloxy, C4-C10 cycloalkylcarbonyloxy, C3-C10 alkylcarbonylalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3-C8 cycloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C3-C8 trialkylsilyl, C3-C8 cycloalkenyloxy, C3-C8 halocycloalkenyloxy, C2-C8 haloalkoxyalkoxy, C2-C8 alkoxyhaloalkoxy, C2-C8 haloalkoxyhaloalkoxy, C3-C10 alkoxycarbonylalkoxy, C2-C8 alkyl(thiocarbonyl)oxy, C3-C8 cycloalkylsulfinyl or C3-C10 halotrialkylsilyl;
    • W3 is C1-C6 alkylene;
    • W4 is —CH2—;
    • R3 is hydroxy, —O−M+, C2-C8 alkylcarbonyloxy, C2-C8 haloalkylcarbonyloxy, C4-C10 cycloalkylcarbonyloxy or C3-C10 alkylcarbonylalkoxy; or benzyloxy, phenyloxy, benzylcarbonyloxy, phenylcarbonyloxy, phenylsulfonyloxy or benzylsulfonyloxy, each optionally substituted on ring members with up to two substituents selected from R21;
    • M+ is a sodium or potassium metal cation;
    • R9 is C1-C6 alkyl;
    • R10 is H, halogen or C1-C6 alkyl;
    • R11 is H or C1-C6 alkyl;
    • R12 is H, halogen, cyano, hydroxy, amino or C1-C6 alkyl;
    • R13 is cyano or nitro;
    • each R14, R15, R18 and R19 is independently H or CH3; or
    • a pair of R14 and R18 is taken together as —CH2CH2CH2— or —CH═CH—CH2—;
    • R20 is H, C1-C6 alkyl, C2-C6 alkenyl or C3-C8 cycloalkyl;
    • T is —CH2CH2— or —CH═CH—;
    • each G is selected from G-1 through G-23 (as depicted in Embodiment 79);
    • r is 0, 1, 2 or 3;
    • each R21 is independently halogen, cyano, hydroxy, nitro, —CHO, —SH, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C4-C10 alkylcycloalkyl, C4-C10 cycloalkylalkyl, C3-C8 cycloalkenyl, C3-C8 halocycloalkenyl, C2-C8 alkoxyalkyl, C4-C10 cycloalkoxyalkyl, C3-C10 alkoxyalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkoxyhaloalkyl, C2-C5 cyanoalkyl, C1-C6 hydroxyalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C8 cycloalkoxy, C3-C8 halocycloalkoxy, C4-C10 cycloalkylalkoxy, C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, C2-C8 alkoxyalkoxy, C2-C8 alkylcarbonyloxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3-C8 cycloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl or C3-C8 cycloalkylsulfonyl; and
    • R22 is independently C1-C6 alkyl or C1-C6 haloalkyl.


Embodiment PB. A compound of Embodiment PA wherein

    • X is CH;
    • A is A-3 or A-5;
    • B2 is C-3;
    • R1 is phenyl, —W1(phenyl), —W1(S-phenyl), —W1(SO2-phenyl), —W2(SO2CH2-phenyl) or —W2(SCH2-phenyl), each optionally substituted on ring members with up to five substituents selected from R21; or -G or —W2G; or C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C3-C8 cycloalkyl, C4-C10 cycloalkylalkyl, C5-C12 alkylcycloalkylalkyl, C3-C8 cycloalkenyl, C3-C8 halocycloalkenyl, C2-C8 alkoxyalkyl, C3-C10 alkoxyalkoxyalkyl, C2-C8 alkylthioalkyl or C2-C8 alkylsulfonylalkyl;
    • R2 is phenyl or —W3(phenyl), each optionally substituted on ring members with up to two substituents selected from R21; or C1-C6 alkyl, C1-C6 haloalkyl, C3-C8 cycloalkyl, C1-C6 alkoxy, C1-C6 alkylthio or C1-C6 alkylsulfonyl;
    • R3 is hydroxy or —O−M+; or phenylsulfonyloxy optionally substituted on ring members with up to two substituents selected from R21;
    • R9 is CH2CH3;
    • R10 is H or CH3;
    • W1 is —CH2—;
    • W3 is —CH2—;
    • G is G-13, G-14, G-15, G-16 or G-17; and
    • each R21 is independently halogen, nitro, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy or C1-C6 alkylthio.


Embodiment PC. A compound of Embodiment PA wherein:

    • X is CH;
    • A is A-1 or A-6;
    • B1 is C-1, B2 is C-3 and B3 is C-1;
    • R1 is phenyl, —W1(phenyl), —W1(S-phenyl), —W1(SO2-phenyl), —W2(SO2CH2-phenyl) or —W2(SCH2-phenyl), each optionally substituted on ring members with up to five substituents selected from R21; or -G or —W2G; or C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C3-C8 cycloalkyl, C4-C10 cycloalkylalkyl, C5-C12 alkylcycloalkylalkyl, C3-C8 cycloalkenyl, C3-C8 halocycloalkenyl, C2-C8 alkoxyalkyl, C3-C10 alkoxyalkoxyalkyl, C2-C8 alkylthioalkyl or C2-C8 alkylsulfonylalkyl;
    • R2 is phenyl or —W3(phenyl), each optionally substituted on ring members with up to two substituents selected from R21; or C1-C6 alkyl, C1-C6 haloalkyl, C3-C8 cycloalkyl, C1-C6 alkoxy, C1-C6 alkylthio or C1-C6 alkylsulfonyl;
    • R3 is hydroxy or —O−M+; or phenylsulfonyloxy optionally substituted on ring members with up to two substituents selected from R21;
    • R11 is H;
    • each R14, R15, R18 and R19 is independently H or CH3;
    • R12 is H, halogen, cyano, C1-C6 alkyl or C3-C8 cycloalkyl;
    • W1 is —CH2—;
    • W3 is —CH2—;
    • G is G-13, G-14, G-15, G-16 or G-17; and
    • each R21 is independently halogen, nitro, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy or C1-C6 alkylthio.


Embodiment PD. A compound of Embodiment PC wherein:

    • A is A-1;
    • R1 is phenyl or —W1(phenyl) each optionally substituted on ring members with up to two substituents selected from R21; or C1-C6 alkyl or C2-C6 alkenyl;
    • R2 is phenyl or CH2(phenyl), each optionally substituted on ring members with up to two substituents selected from R21; or C1-C6 alkyl, C3-C8 cycloalkyl or C1-C6 alkylthio;
    • R3 is hydroxy; or phenylsulfonyloxy substituted with CH3 at the 4-position; and
    • each R21 is independently fluorine, chlorine, CH3, CF3, OCH3, OCF3 or SCH3.


Embodiment PE. A compound of Embodiment PD wherein:

    • R1 is phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 4-methylphenyl, 2-methylphenyl, 4-methoxyphenyl, 2,3-dimethylphenyl, CH2(phenyl), CH3 or CH2CH3;
    • R2 is phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, CH2CH3, c-Pr or SCH3.


Specific embodiments include the compound of Formula 1P which is:

  • 5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2,3-diphenyl-4(3H)-pyrimidinone.


This invention also relates to a method for controlling undesired vegetation comprising applying to the locus of the vegetation a herbicidally effective amount of a compound of the invention (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.


This invention also includes herbicidal mixture comprising (a) a compound of Formula 1P and (b) an additional herbicidal ingredient selected from a photosystem II inhibitor. Also noteworthy as embodiments are herbicidal compositions of the present invention comprising the compounds of embodiments described above.


“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, but are not limited to ametryn, atrazine, cyanazine, desmetryne, dimethametryn, prometon, prometryne, propazine, simazine, simetryn, terbumeton, terbuthylazine, terbutryne, trietazine, hexazinone, metamitron, metribuzin, amicarbazone, bromacil, lenacil, terbacil, chloridazon, desmedipham, phenmedipham, chlorobromuron, chlorotoluron, chloroxuron, dimefuron, diuron, ethidimuron, fenuron, fluometuron, isoproturon, isouron, linuron, methabenzthiazuron, metobromuron, metoxuron, monolinuron, neburon, siduron, tebuthiuron, propanil, pentanochlor, bromofenoxim, bromoxynil, ioxynil, bentazon, pyridate and pyridafol.


“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 DNA synthesis and cell growth. Examples of AHAS inhibitors include but are not limited to amidosulfuron, azimsulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, flupyrsulfuron-methyl (including sodium salt), foramsulfuron, halosulfuron-methyl, imazosulfuron, iodosulfuron-methyl (including sodium salt), mesosulfuron-methyl, metazosulfuron, metsulfuron-methyl, nicosulfuron, oxasulfuron, primisulfuron-methyl, propyrisulfuron, prosulfuron, pyrazosulfuron-ethyl, rimsulfuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron-methyl, triasulfuron, tribenuron-methyl, trifloxysulfuron (including sodium salt), triflusulfuron-methyl, tritosulfuron, imazapic, imazamethabenz-methyl, imazamox, imazapyr, imazaquin, imazethapyr, cloransulam-methyl, diclosulam, florasulam, flumetsulam, metosulam, penoxsulam, bispyribac-sodium, pyribenzoxim, pyriftalid, pyrithiobac-sodium, pyriminobac-methyl, thiencarbazone, flucarbazone-sodium and propoxycarbazone-sodium.


“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 but are not limited to clodinafop, cyhalofop, diclofop, fenoxaprop, fluazifop, haloxyfop, propaquizafop, quizalofop, alloxydim, butroxydim, clethodim, cycloxydim, pinoxaden, profoxydim, 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.


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 but are not limited to aminocyclopyrachlor, aminopyralid benazolin-ethyl, chloramben, clomeprop, clopyralid, dicamba, 2,4-D, 2,4-DB, dichlorprop, fluroxypyr, mecoprop, MCPA, MCPB, 2,3,6-TBA, picloram, triclopyr, quinclorac, quinmerac.


“EPSP (5-enol-pyruvylshikimate-3-phosphate) 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).


One or more of the following methods and variations as described in Schemes 1-18 can be used to prepare the compounds of Formula 1. The definitions of A, B1, B2, B3, R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R12 and R13 in the compounds of Formulae 1-34 below are as defined above in the Summary of the Invention unless otherwise noted. Compounds of Formulae 1a-1h are various subsets of the compounds of Formula 1, and all substituents for Formulae 1a-1h are as defined above for Formula 1.


Compounds of Formula 1a, 1b or 1c (where R3 is hydroxy) can be prepared via the two-step process shown in Schemes 1a, 1b and 1c respectively. Intermediate 4a, 4b or 4c can be prepared by reacting dione 2 with intermediate 3 where G is a nucleophilic reaction leaving group (e.g., G1 is a halogen, alkoxycarbonyl, haloalkylcarbonyloxy, haloalkoxycarbonyloxy, pyridinyl or imidazoyl group). Reaction of intermediate 4a, 4b or 4c with the appropriate cyano compound (e.g., acetone cyanohydrin, potassium cyanide, sodium cyanide) in the presence of a base such as triethylamine or pyridine leads to a compound of Formula 1a, 1b or 1c. Alternatively a fluoride anion source such as potassium fluoride or cesium fluoride and optionally in the presence of a phase transfer catalyst (e.g. tetrabutyl ammonium bromide, etc.) can be used in this transformation. A solvent such as dimethylsulfoxide, N,N-dimethylformamide, acetonitrile or dichloromethane at ambient temperature to the reflux temperature of the solvent can lead to a compound of Formula 1a, 1b or 1c. (Formula 1a is Formula 1 wherein A is A-1; Formula 1b is Formula 1 wherein A is A-2; Formula 1c is Formula 1 wherein A is A-3.) Alternatively, compounds of Formula 1a, 1b or 1c can be prepared by Process 2 (in Schemes 1a, 1b and 1c respectively) by reacting dione 2a, 2b or 2c with intermediate 3 in the presence of a cyano compound or a fluoride anion source along with a base. For additional reaction conditions for this general coupling methodology, see Edmunds, A. in Modern Crop Protection Compounds; Kramer, W. and Schirmer, U., Eds.; Wiley, Weinheim, 2007; Chapter 4.3 and references cited therein.




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Compounds of Formula 1a, 1b or 1c can also be prepared as shown in Scheme 2, by reacting dione 2a, 2b or 2c with intermediate 3a in the presence of a base or Lewis acid. For reaction conditions for this general coupling methodology, see Edmunds, A. in Modern Crop Protection Compounds; Kramer, W. and Schirmer, U., Eds.; Wiley, Weinheim, 2007; Chapter 4.3 and references cited therein.




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As shown in Scheme 3, intermediate 4a, 4b or 4c can also be prepared by allowing dione 2a, 2b or 2c to react with acid 6 in the presence of a dehydrating condensation agent such as 2-chloro-1-pyridinium iodide (known as the Mukaiyama coupling agent), dicyclohexyl carbodiimide (DCC) or the like and optionally in the presence of a base. For additional reaction conditions for this general enol ester coupling methodology, see Edmunds, A. in Modern Crop Protection Compounds; Kramer, W. and Schirmer, U., Eds.; Wiley, Weinheim, 2007; Chapter 4.3 and references cited therein.




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Intermediate 4a, 4b or 4c can also be made by the palladium-catalyzed carbonylation reaction of a compound of Formula 7 in the presence of dione 2a, 2b or 2c (Scheme 4). For reaction conditions for this general enol ester forming methodology, see Edmunds, A. in Modern Crop Protection Compounds; Kramer, W. and Schirmer, U., Eds.; Wiley, Weinheim, 2007; Chapter 4.3 and references cited therein.




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Compounds of Formula 1a, 1b or 1c (where R3 is bonded through oxygen) are prepared by reacting compounds of Formula 1a, 1b or 1c with intermediate 8 where X is a nucleophilic reaction leaving group, also known as a nucleofuge in the presence of a base as shown in Scheme 5. Alternatively, compounds of Formula 1a, 1b and 1c (where R3 is bonded through nitrogen, sulfur or carbon) can be prepared using the appropriate halogenating agent followed by nucleophilic addition. For reaction conditions for this general functionalization method, see Edmunds, A. or Almisick A. V. in Modern Crop Protection Compounds; Kramer, W. and Schirmer, U., Eds.; Wiley, Weinheim, 2007; Chapter 4.3 or Chapter 4.4, and references cited therein.




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As shown in Scheme 6, compounds of Formula 1d (i.e. Formula 1 wherein A is A-4 and R3 is OH) can be prepared by the reaction of intermediate 9 with intermediate 3 in the presence of a Lewis base, for example n-butyllithium or lithium diisopropylamide in an appropriate solvent such as tetrahydrofuran or diethyl ether. For reaction conditions for this type of transformation, see JP 2003327580.




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Compounds of Formula 1e (i.e. Formula 1 wherein A is A-5 and R3 is OH) can be prepared via a two-step process as shown in Scheme 7. Intermediate 12 can be prepared by reacting pyrazole 11 with intermediate 3 where G1 is a nucleophilic reaction leaving group (i.e. G1 is a halogen atom, alkoxycarbonyl, haloalkylcarbonyloxy, benzoyloxy, pyridinyl or imidazoyl group). Reaction of intermediate 12 with the appropriate cyano compound in the presence of a base leads to a compound of Formula 1e. Alternatively, a compound of Formula 1e can be prepared directly by reacting intermediate 11 with intermediate 3 (Process 2, Scheme 7) in the presence of a cyano compound or a fluoride anion source with a base. For reaction conditions for this general coupling methodology, see Almisick A. V. in Modern Crop Protection Compounds; Kramer, W. and Schirmer, U., Eds.; Wiley, Weinheim, 2007; Chapter 4.4, and references cited therein.




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Compounds of Formula 1f (i.e. Formula 1 wherein A is A-5) wherein R3 is bonded through oxygen can be prepared by reacting a compound of Formula 1e with intermediate 8 (where X is a nucleophilic reaction leaving group, also known as a nucleofuge) in the presence of a base as shown in Scheme 8. Alternatively compounds of Formula 1f wherein R3 is bonded through nitrogen, sulfur or carbon can be prepared using the appropriate halogenating agent followed by nucleophilic displacement. For reaction conditions for these general functionalization methods, see Almisick A. V. in Modern Crop Protection Compounds; Kramer, W. and Schirmer, U., Eds.; Wiley, Weinheim, 2007; Chapter 4.4, and references cited therein.




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Compounds of Formula 17 can be prepared by reacting intermediate 3 with a compound Formula 16 in an appropriate solvent in the presence of a base. Thereafter intermediate 17 can be rearranged into the compound of Formula 1g (i.e. Formula 1 wherein A is A-7) in the presence of a cyano compound and a base as shown in Scheme 9. For reaction conditions for this general coupling methodology, see Almisick A. V. in Modern Crop Protection Compounds; Kramer, W. and Schirmer, U., Eds.; Wiley, Weinheim, 2007; Chapter 4.4, and references cited therein.




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Compounds of Formula 19 can be prepared from corresponding compounds of Formula 1g wherein R13 is an alkoxycarbonyl in the presence of an acid such as hydrogen chloride, sulfuric or acetic acid and optionally in the presence of a solvent such as tetrahydrofuran, diethyl ether or dichloromethane as shown in Scheme 10. Intermediate 19 is then reacted with an orthoformate ester or N,N-dimethylformamide dimethylacetal (DMF-DMA) in the presence of an acid to obtain intermediate 20. Reaction of intermediate 20 with hydroxylamine hydrochloride salt in a solvent such as ethanol, acetonitrile, water or acetic acid provides isoxazole compounds of Formula 1h (i.e. Formula 1 wherein A is A-6 and R11 is H). For reaction conditions for this general cyclization methodology, see Almisick A. V. in Modern Crop Protection Compounds; Kramer, W. and Schirmer, U., Eds.; Wiley, Weinheim, 2007; Chapter 4.4, and references cited therein.




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As illustrated in Scheme 11, sulfoxides and sulfones of Formula 1 wherein R2 is a substituent bonded through a sulfoxide or sulfone radical can be prepared by oxidation of the compounds of Formula 1 wherein R2 is a substituent bonded through a sulfide radical. In a typical procedure, an oxidizing agent in an amount from 1 to 4 equivalents depending on the oxidation state of the product desired is added to a solution of the compound of Formula 1 in a solvent. Useful oxidizing agents include Oxone® (potassium peroxymonosulfate), hydrogen peroxide, sodium periodate, peracetic acid and 3-chloroperbenzoic acid. The solvent is selected with regard to the oxidizing agent employed. Aqueous ethanol or aqueous acetone is preferably used with potassium peroxymonosulfate, and dichloromethane is generally preferable with 3-chloroperbenzoic acid. Useful reaction temperatures typically range from 0 to 90° C. Particular procedures useful for oxidizing sulfides to sulfoxides and sulfones are described by Brand et al., J. Agric. Food Chem. 1984, 32, 221-226 and references cited therein.




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One skilled in the art will realize that acid chlorides of Formula 3d (i.e. Formula 3 wherein G1 is Cl) are easily prepared from the acid of Formula 6 (Scheme 12) by numerous well-known methods. For example reacting the acid with a chlorinating reagent such as oxalyl chloride or thionyl chloride in a solvent such as dichloromethane or toluene and optionally in the presence of a catalytic amount of N,N-dimethylformamide can provide the corresponding acid chloride of Formula 3d.




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Compounds of Formula 6 can be prepared from esters of Formula 23 by numerous well-known methods, for example standard saponification procedures using aqueous bases such as LiOH, NaOH or KOH in a solvent such methanol or ethanol as described in Scheme 13. Alternatively, a dealkylating agent such as lithium iodide or trimethylsilyl iodide can be used in the presence of a base in a solvent such as pyridine or ethyl acetate. Additional reaction procedures for deesterification can be found in PCT Patent Publication WO 2006/133242. Boron tribromide (BBr3) can alternatively be used to prepare a compound of Formula 6 from a compound of Formula 23 in a solovent such as dichloromethane. Procedures using boron tribromide can be found in Bioorg. & Med. Chem. Lett. 2009, 19(16), 4733-4739.




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Pyrimidinone esters of Formula 23a (i.e. Formula 23 whererin Alk is ethyl, X is CH and Y is C(O)) are prepared as illustrated in Scheme 14 by N-alkylation of pyridones of Formula 26 with agents such as alkyl halides in the presence of a base such as sodium hydride or potassium carbonate in a solvent such as N,N-dimethylformamide, tetrahydrofuran or diethyl ether.




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Pyrimidinone esters of Formula 23a can be made by the method of Scheme 15. In this method an methylene malonate of Formula 28 is cyclized with an amidine salt of Formula 29 wherein X is a halogen or sulfonate counter ion in the presence of excess base such as sodium alkoxide or potassium carbonate in an appropriate solvent such as ethanol (generally at the reflux temperature of the solvent) to give the corresponding pyrimidinone of Formula 3f. Examples of this synthetic method are reported in PCT Patent Publication WO 2006/133242 or Tetrahedron 2001, 57, 2689.




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Pyrimidinone esters of Formula 26 can be prepared by the method of Scheme 16. In this method, an ethylene malonate of Formula 28 is cyclized with an amidine salt Formula 29a wherein X is a halogen or sulfonate counter ion in the presence of excess base such as sodium alkoxide or potassium carbonate in an appropriate solvent such as methanol (generally at the reflux temperature of the solvent) to give the corresponding pyrimidinone of Formula 26. Examples of this synthetic procedure are reported in PCT Patent Publication WO 2006/133242, Tetrahedron 2001, 57, 2689.




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Thiones of Formula 23b (i.e. Formula 23 wherein Alk is ethyl, X is CH and Y is S(O)2) can be made by the method of Scheme 17. In this method amidines of Formula 29 is reacted with acetal 30 in the presence of a base such as triethylamine, pyridine or potassium carbonate to give the corresponding azabutadiene 31. Reacting this compound with the sulfonic acid chloride 32 as shown in Scheme 17 in the presence of a base such as triethylamine, pyridine or potassium carbonate in an appropriate solvent results in the corresponding compound of Formula 33. The corresponding thiones of formula 23b can be obtained by reacting the compound of Formula 33 with iodomethane and subsequent treatment with a base such as triethylamine. Examples of this synthetic methodology are reported in Synthesis 2000, 5, 695.




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Triazines of Formula 23c (i.e. Formula 23 wherein Alk is ethyl, X is N and Y is C(O)) can be made by the method of Scheme 18. In this method a ketomalonate of Formula 34 is cyclized with a semicarbazide of Formula 29c wherein X is a halogen or sulfonate counter ion with or without the presence of excess base such as sodium alkoxide or potassium carbonate in an appropriate solvent such as ethanol or t-butanol (generally at the reflux temperature of the solvent) to the corresponding triazine of Formula 23c. Examples of this synthetic methodology are found in Eur. J. Med. Chem. 2008, 43(5), 1085, Bull. Soc. Chim. Fr. 1976, (11-12, Pt. 2), 1825 and J. Org. Chem. 1962, 27, 976.




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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 sequence 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 invention 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 at 400 MHz unless otherwise noted; “s” means singlet, “m” means multiplet, “br s” means broad singlet, “d” means doublet, “t” means triplet, “dt” means doublet of triplets, “q” means quartet and “sep” means septet.


EXAMPLE 1
Preparation of 5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2,3-diphenyl-4(3H)-pyrimidinone (Compound 2)
Step A: Preparation of N-phenylbenzenecarboximidamide sodium salt

To a stirred solution of sodium bis(trimethylsilyl)amide (1.0 M in tetrahydrofuran, 21.5 mL, 21.5 mmol) in tetrahydrofuran (10 mL) was added aniline (2.0 g, 21.5 mmol) and allowed to stir for 10 min at room temperature. Benzonitrile (2.21 g, 21.5 mmol) was added, and the reaction mixture was stirred for 1 h at room temperature. The solid that precipitated was filtered, washed with diethyl ether and dried under reduced pressure to afford the title product as an off-white solid (4.0 g), which was used without further purification in the next step.


Step B: Preparation of (A) 1,6-dihydro-6-oxo-1,2-diphenyl-5-pyrimidinecarboxylic acid ethyl ester and (B) 1,6-dihydro-6-oxo-1,2-diphenyl-5-pyrimidinecarboxylic acid

To a stirred solution of N-phenylbenzenecarboximidamide sodium salt (i.e. the product from Step A) (6.0 g, 27.5 mmol) in acetonitrile (30 mL) was added ammonium chloride (1.47 g, 27.5 mmol) followed by diethyl ethoxymethylenemalonate (5.94 g, 27.5 mmol). The reaction mixture was heated and stirred at reflux for 2 h. The reaction mixture was concentrated under reduced pressure to give a residue. Water (30 mL) was added to the residue, followed by a saturated solution of sodium bicarbonate (30 mL), and the mixture was extracted with ethyl acetate. The aqueous layer was separated and retained. The organic layer was dried (MgSO4) and concentrated under reduced pressure. The resulting residue was purified by column chromatography eluting with 30% ethyl acetate in hexanes to afford the title product (A) as a white solid (2.80 g).



1H NMR (CDCl3) δ 8.81 (s, 1H), 7.11-7.33 (m, 10H), 4.41 (m, 2H), 1.39 (m, 3H).


The above retained aqueous layer was acidified with 1 N hydrochloric acid until the pH was 1-2, and the mixture was extracted with dichloromethane. The organic layer was dried (MgSO4) and concentrated under reduced pressure to provide a solid, which was washed with diethyl ether and dried under reduced pressure to afford the title product (B) as a white solid (680 mg).



1H NMR (DMSO-d6) δ 13.03 (s, 1H), 8.79 (s, 1H), 7.22-7.36 (m, 10H).


Step B1: Preparation of 1,6-dihydro-6-oxo-1,2-diphenyl-5-pyrimidinecarboxylic acid (alternate preparation to Step B, product (B))

To a stirred solution of 1,6-dihydro-6-oxo-1,2-diphenyl-5-pyrimidinecarboxylic acid ethyl ester (i.e. Step B product (A)) (2.30 g, 7.18 mmol) in pyridine (15 mL) was added lithium iodide (2.46 g, 18.0 mmol). The reaction mixture was heated to reflux with stirring for 24 h. The reaction mixture was concentrated under reduced pressure. To the resulting residue was added water (10 mL) followed by 1 N hydrochloric acid until the pH was 7. The solution was filtered though Celite® diatomaceous filter aid. The filtrate was acidified with 1 N hydrochloric acid until the pH was 1, and the mixture was extracted with dichloromethane. The organic layer was dried (MgSO4) and concentrated under reduced pressure to afford a solid, which was washed with diethyl ether and dried under reduced pressure to afford the title product as a white solid (1.40 g).



1H NMR (DMSO-d6) δ 13.03 (s, 1H), 8.79 (s, 1H), 7.22-7.36 (m, 10H).


Step C: Preparation of 3-oxo-1-cyclohexen-1-yl 1,6-dihydro-6-oxo-1,2-diphenyl-5-pyrimidinecarboxylate

To a stirred solution of 1,6-dihydro-6-oxo-1,2-diphenyl-5-pyrimidinecarboxylic acid (i.e. Step B product (B) or the product from Step B1) (1.40 g, 4.8 mmol) in dichloromethane (30 mL) was added oxalyl chloride (1.21 g, 9.61 mmol) at 0° C. followed by catalytic amount (2 drops) of N,N-dimethylformamide. The reaction mixture was allowed to warm to room temperature and stir for 1 h. Then the reaction mixture was concentrated under reduced pressure. To the resulting residue was added dichloromethane (30 mL), 1,3-cyclohexanedione (646 mg, 5.76 mmol), followed by triethylamine (976 mg, 9.60 mmol), and the reaction mixture was stirred at room temperature for 30 min. Saturated aqueous ammonium chloride solution was added, and the mixture was extracted with dichloromethane. The organic layer was dried (MgSO4) and concentrated under reduced pressure. The residue was purified by column chromatography eluting with 50% ethyl acetate in hexanes to afford the title product as a white solid (1.1 g).



1H NMR (CDCl3) δ 8.89 (s, 1H), 7.31-7.36 (m, 5H), 7.24-7.26 (m, 3H), 7.12-7.15 (m, 2H), 6.04 (m, 1H), 2.68 (m, 2H), 2.45 (m, 2H), 2.11 (m, 2H).


Step D: Preparation of 5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2,3-diphenyl-4(3H)-pyrimidinone (Compound 2)

To a stirred solution of 3-oxo-1-cyclohexen-1-yl 1,6-dihydro-6-oxo-1,2-diphenyl-5-pyrimidinecarboxylate (i.e. the product from Step C) (640 mg, 1.65 mmol) in acetonitrile (20 mL) was added triethylamine (401 mg, 3.97 mmol), followed by a catalytic amount of acetone cyanohydrin (3 drops). The reaction mixture was stirred for 24 h at room temperature and then concentrated under reduced pressure. To the resulting residue was added dichloromethane and 1 N hydrochloric acid. The organic layer was separated, and the aqueous layer was extracted with dichloromethane. The combined organic layers were dried (MgSO4) and concentrated under reduced pressure. The residue was purified by column chromatography eluting with 100% ethyl acetate to afford the title product, a compound of the present invention, as a white solid (150 mg).



1H NMR (CDCl3) δ 8.24 (s, 1H), 7.12-7.34 (m, 10H), 2.70 (m, 2H), 2.48 (m, 2H), 2.03 (m, 2H).


EXAMPLE 2
Preparation of 5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-phenyl-3-(phenylmethyl)-4(3H)-pyrimidinone (Compound 17)
Step A: Preparation of N-(phenylmethyl)-benzenecarboximidamide

To a stirred solution of ethylbenzimidate hydrochloride (3.0 g, 16.2 mmol) in N,N-dimethylformamide (10 mL) was added triethylamine (1.60 g, 16.2 mmol). The reaction mixture was allowed to stir at room temperature for 1 h and then filtered to remove triethylamine salts, which were rinsed with N,N-dimethylformamide (5 mL). Benzylamine (1.23 g, 11.5 mmol) was added to the filtrate, and the mixture was heated to 65° C. for 24 h. To the cooled mixture was added water (80 mL) and ethyl acetate. The organic layer was washed with water and brine, then dried (MgSO4) and concentrated under reduced pressure to afford the title product as a clear oil (2.80 g).



1H NMR (CDCl3) δ 7.61 (m, 2H), 7.26-4.43 (m, 8H), 4.57 (m, 2H), 4.37 (m, 1H), 1.42 (m, 1H).


Step B: Preparation of ethyl 1,6-dihydro-6-oxo-2-phenyl-1-(phenylmethyl)-5-pyrimidinecarboxylate

To a stirred solution of N-(phenylmethyl)-benzenecarboximidamide (i.e. the product from Step A) (2.54 g, 12.1 mmol) in ethanol (15 mL) was added diethyl ethoxymethylenemalonate (2.61 g, 12.1 mmol), and the reaction mixture was heated to reflux for 24 h. The reaction mixture was then allowed to cool to room temperature and concentrated under reduced pressure. The residue was purified by column chromatography eluting with 30% ethyl acetate in hexanes to afford the title product as a white solid (2.9 g).



1H NMR (CDCl3) δ 8.71 (s, 1H), 7.51 (m, 1H), 7.42 (m, 2H), 7.33 (m, 2H), 7.23 (m, 3H), 6.93 (m, 2H), 5.28 (s, 2H), 4.42 (m, 2H), 1.40 (m, 3H).


Step C: Preparation of 1,6-dihydro-6-oxo-2-phenyl-1-(phenylmethyl)-5-pyrimidinecarboxylic acid

To a stirred solution of ethyl 1,6-dihydro-6-oxo-2-phenyl-1-(phenylmethyl)-5-pyrimidinecarboxylate (i.e. the product from Step B) (2.9 g, 8.6 mmol) in pyridine (15 mL) was added lithium iodide (3.01 g, 21.7 mmol). The reaction mixture was heated to reflux for 4 h, cooled, and then stirred at room temperature for 72 h. The reaction mixture was concentrated under reduced pressure. To the resulting residue was added water (10 mL), followed by 1 N hydrochloric acid until the pH was 7. The solution was filtered through Celite® diatomaceous filter aid, and the filtrate was acidified with 1 N hydrochloric acid until the pH was 1. The mixture was extracted with dichloromethane, and the organic layer was dried (MgSO4) and concentrated under reduced pressure to afford a solid, which was washed with diethyl ether and dried under reduced pressure to afford the title product as a white solid (2.2 g).


Step D: Preparation of 3-oxo-1-cyclohexen-1-yl 1,6-dihydro-6-oxo-2-phenyl-1-(phenylmethyl)-5-pyrimidinecarboxylate

To a stirred solution of 1,6-dihydro-6-oxo-2-phenyl-1-(phenylmethyl)-5-pyrimidinecarboxylic acid (i.e. the product from Step C) (1.00 g, 3.26 mmol) in dichloromethane (30 mL) at 0° C., was added oxalyl chloride (823 mg, 6.53 mmol) followed by a catalytic amount of N,N-dimethylformamide (2 drops). The reaction mixture was allowed to warm to room temperature and stir for 1 h. Then the reaction mixture was concentrated under reduced pressure. To the resulting residue was added dichloromethane (30 mL) and 1,3-cyclohexanedione (440 mg, 3.90 mmol), followed by triethylamine (990 mg, 9.80 mmol), and the reaction mixture was stirred at room temperature for 30 min Saturated aqueous ammonium chloride solution was added to the reaction mixture, which was then extracted with dichloromethane. The organic layer was dried (MgSO4) and concentrated under reduced pressure. The residue was purified by column chromatography eluting with 50% ethyl acetate in hexanes to afford the title product as a white solid (500 mg).



1H NMR (CDCl3) δ 8.81 (s, 1H), 7.55 (m, 1H), 7.45 (m, 2H), 7.37 (m, 2H), 7.25 (m, 3H), 6.95 (m, 2H), 6.03 (s, 1H), 5.30 (s, 2H), 2.69 (m, 2H), 2.46 (m, 2H), 2.12 (m, 2H).


Step E: Preparation of 5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-phenyl-3-(phenylmethyl)-4(3H)-pyrimidinone (Compound 17)

To a stirred solution of 3-oxo-1-cyclohexen-1-yl 1,6-dihydro-6-oxo-2-phenyl-1-(phenylmethyl)-5-pyrimidinecarboxylate (i.e. the product from Step D) (450 mg, 1.12 mmol) in acetonitrile (15 mL) was added triethylamine (272 mg, 2.69 mmol), followed by a catalytic amount (3 drops) of acetone cyanohydrin. The reaction mixture was stirred for 24 h at room temperature and then concentrated under reduced pressure. To the resulting residue were added dichloromethane and 1 N hydrochloric acid, and the aqueous layer was extracted with dichloromethane. The organic layer was dried (MgSO4) and concentrated under reduced pressure. The residue was purified by column chromatography eluting with ethyl acetate to afford the title product, a compound of the present invention, as a white solid (160 mg).



1H NMR (CDCl3) δ 16.44 (br s, 1H), 8.17 (s, 1H), 7.47 (m, 1H), 7.37 (m, 2H), 7.21-7.30 (m, 5H), 6.95 (m, 2H), 5.20 (s, 2H), 2.72 (m, 2H), 2.51 (m, 2H), 2.06 (m, 2H).


Example 3
Preparation of 5-[(1-ethyl-5-hydroxy-1H-pyrazol-4-yl)carbonyl]-2-phenyl-3-(phenylmethyl)-4(3H)-pyrimidinone (Compound 20)
Step A: Preparation of 1-ethyl-1H-pyrazol-5-yl 1,6-dihydro-6-oxo-2-phenyl-1-(phenylmethyl)-5-pyrimidinecarboxylate

To a stirred solution of 1,6-dihydro-6-oxo-2-phenyl-1-(phenylmethyl)-5-pyrimidinecarboxylic acid (i.e. the product from Example 2, Step C) (1.20 g, 3.92 mmol) in dichloromethane (30 mL) was added oxalyl chloride (998 mg, 7.84 mmol) at 0° C. followed by a catalytic amount (4-drops) of N,N-dimethylformamide. The reaction mixture was allowed to warm to room temperature and stir for 1 h. The reaction mixture was then concentrated under reduced pressure. To the resulting residue was added dichloromethane (30 mL) and 5-hydroxy-1-ethyl-1H-pyrazole, (572 mg, 4.7 mmol), followed by triethylamine (1.18 g, 11.8 mmol), and the reaction mixture was stirred at room temperature for 30 min. Saturated aqueous ammonium chloride solution was added to the reaction mixture, which was then extracted with dichloromethane. The organic layer was dried (MgSO4) and concentrated under reduced pressure. The residue was purified by column chromatography eluting with 70% ethyl acetate in hexanes to afford the title product as a white solid (700 mg).



1H NMR (CDCl3) δ 8.90 (s, 1H), 7.56 (m, 1H), 7.46 (m, 3H), 7.38 (m, 2H), 7.26 (m, 3H), 6.95 (m, 2H), 6.29 (m, 1H), 5.34 (s, 2H), 4.19 (m, 2H), 1.45 (m, 3H).


Step B: Preparation of 5-[(1-ethyl-5-hydroxy-1H-pyrazol-4-yl)carbonyl]-2-phenyl-3-(phenylmethyl)-4(3H)-pyrimidinone (Compound 20)

To a stirred solution of 1-ethyl-1H-pyrazol-5-yl 1,6-dihydro-6-oxo-2-phenyl-1-(phenylmethyl)-5-pyrimidinecarboxylate (i.e. the product from Step A) (650 mg, 1.62 mmol) in acetonitrile (15 mL) was added triethylamine (393 mg, 3.70 mmol), followed by a catalytic amount (5 drops) of acetone cyanohydrin. The reaction mixture was stirred for 24 h at room temperature and then concentrated under reduced pressure. To the residue were added dichloromethane and 1 N hydrochloric acid, and the aqueous layer was extracted with dichloromethane. The organic layer was dried (MgSO4) and concentrated under reduced pressure. The residue was purified by column chromatography eluting with 10% methanol in ethyl acetate to afford the title product, a compound of the present invention, as a white solid (150 mg).



1H NMR (CDCl3) δ 8.56 (s, 1H), 7.86 (s, 1H), 7.53 (m, 1H), 7.39-7.46 (m, 4H), 7.24 (m, 3H), 6.97 (m, 2H), 5.33 (s, 2H), 4.04 (m, 2H), 1.42 (m, 3H).


EXAMPLE 4
Step A: Preparation of 5-[[1-ethyl-5-[[(4-methylphenyl)sulfonyl]oxy]-1H-pyrazol-4-yl]carbonyl]-2-phenyl-3-(phenylmethyl)-4(3H)-pyrimidinone (Compound 21)

To a stirred solution of 5-[(1-ethyl-5-hydroxy-1H-pyrazol-4-yl)carbonyl]-2-phenyl-3-(phenylmethyl)-4(3H)-pyrimidinone (i.e. the product from Example 3, Step B) (300 mg, 0.75 mmol) in acetonitrile (10 mL) was added triethylamine (116 mg, 1.12 mmol), followed by p-toluenesulfonyl chloride (171 mg, 0.90 mmol), and the reaction mixture was stirred at room temperature for 72 h. Saturated aqueous ammonium chloride solution was added to the mixture, and the aqueous layer was extracted with dichloromethane. The organic layer was dried (MgSO4) and concentrated under reduced pressure. The residue was purified by column chromatography eluting with 50% ethyl acetate in hexanes to afford the title product, a compound of the present invention, as a white solid (160 mg).



1H NMR (CDCl3) δ 8.07 (s, 1H), 7.84 (s, 1H), 7.74 (m, 2H), 7.44 (m, 2H), 7.25-7.35 (m, 8H), 6.95 (m, 2H), 5.23 (s, 2H), 4.00 (m, 2H), 2.41 (s, 3H), 1.42 (m, 3H).


EXAMPLE 5
Preparation of 3-(3-fluoro-2-methylphenyl)-5-[2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-phenyl-4(3H)-pyrimidinone (Compound 47)
Step A: Preparation of N-(3-fluro-2-methylphenyl)benzenecarboximidamide sodium salt (1:1)

To a stirred solution of sodium bis(trimethylsilyl)amide (1.0 M in tetrahydrofuran, 200.0 mL, 200.0 mmol) was added 3-fluoro-2-methylaniline (25.0 g, 200.0 mmol) and allowed to stir for 10 min at room temperature. Benzonitrile (20.6 g, 200.0 mmol) was added, and the reaction mixture was stirred for 1 h at room temperature. The reaction mixture was concentrated and the solid that formed was filtered, washed with diethyl ether and dried under reduced pressure to afford the title product as a grey solid (51.0 g), which was used without further purification in the next step.


Step B: Preparation of 1-(3-fluoro-2-methylphenyl)-1,6-dihydro-6-oxo-2-phenyl-5-pyrimidinecarboxylic acid

To a stirred solution of N-(3-fluro-2-methylphenyl)benzenecarboximidamide sodium salt (1:1) (i.e. the product from Example 5, Step A) (51.0 g, 200 mmol) in acetonitrile (300 mL) was added diethyl ethoxymethylenemalonate (44.04 g, 200 mmol). The reaction was stirred at room temperature for 30 min followed by the addition of water (3.6 mL, 200 mmol). The reaction was then stirred for another 30 min Water (100 mL) was added to the residue, followed by a saturated solution of sodium bicarbonate (300 mL), and the mixture was extracted with ethyl acetate. The aqueous layer was acidified with concentrated hydrochloric acid until the pH was 1-2, and the mixture was extracted with dichloromethane. The organic layer was dried (MgSO4) and concentrated under reduced pressure to provide a solid, which was washed with diethyl ether and dried under reduced pressure to afford the title product as a off-white solid (18 g).



1H NMR (CDCl3) δ 12.68 (s, 1H), 9.15 (s, 1H), 7.43 (m, 1H), 7.19-7.38 (m, 5H), 7.12 (m, 1H), 6.88 (m, 1H), 2.03 (s, 3H).


Step C: Preparation of 3-oxo-1-cyclohexen-1-yl 1-(3-fluoro-2-methylphenyl)-1,6-dihydro-6-oxo-2-phenyl-5-pyrimidinecarboxylate

To a stirred solution of 1-(3-fluoro-2-methylphenyl)-1,6-dihydro-6-oxo-2-phenyl-5-pyrimidinecarboxylic acid (i.e. the product from Example 5, Step B) (41.0 g, 126 mmol) in dichloromethane (400 mL) was added oxalyl chloride (31.05 g, 252.0 mmol) at 0° C. followed by a catalytic amount (7 drops) of N,N-dimethylformamide. The reaction mixture was allowed to warm to room temperature and stir for 1 h. The reaction mixture was then concentrated under reduced pressure. To the resulting residue was added dichloromethane (400 mL), 1,3-cyclohexanedione (17.03 g, 152 mmol), followed by triethylamine (38.30 g, 379 mmol) and the reaction mixture was stirred at room temperature for 30 min. Saturated aqueous ammonium chloride solution was added, and the mixture was extracted with dichloromethane. The organic layer was washed once with water. Then the organic layer was dried (MgSO4) and concentrated under reduced pressure. The resulting solid was washed with chlorobutane to afford the title product pure as an off-white solid (37.6 g).



1H NMR (CDCl3) δ 8.92 (s, 1H), 7.24-7.40 (m, 5H), 7.18 (m, 1H), 7.05 (m, 1H), 6.87 (m, 1H), 6.05 (s, 1H), 2.68 (m, 2H), 2.45 (m, 2H), 2.11 (m, 2H), 2.03 (s, 3H).


Step D: Preparation of 3-(3-fluoro-2-methylphenyl)-5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-phenyl-4(3H)-pyrimidinone

To a stirred solution of 3-oxo-1-cyclohexen-1-yl 1-(3-fluoro-2-methylphenyl)-1,6-dihydro-6-oxo-2-phenyl-5-pyrimidinecarboxylate (i.e. the product from Example 5, Step C) (42 g, 100.4 mmol) in acetonitrile (200 mL) was added cesium fluoride (30.5 g, 200.8 mmol). The reaction mixture was stirred for 24 h at room temperature. Water and ethyl acetate was added to the reaction mixture and the water layer was extracted several times with ethyl acetate. The combined organic layers were dried (MgSO4) and concentrated under reduced pressure. The resulting solid was washed several times with ether and filtered, followed by the addition 60 mL of ethyl acetate and let stir for 2 h. The resulting solid was then washed again with ether and dried under reduced pressure to afford the title product, a compound of the present invention, as a yellow solid (26 g).



1H NMR (CDCl3) δ 16.38 (s, 1H), 8.28 (s, 1H), 7.21-7.34 (m, 5H), 7.11 (m, 1H), 7.00 (m, 1H), 6.86 (m, 1H), 2.70 (m, 2H), 2.47 (m, 2H), 2.10 (m, 3H), 2.03 (m, 2H).


EXAMPLE 6
Preparation of 5-[5-cyclopropyl-4-isoxazolyl)carbonyl]-2,3-diphenyl-4(3H)-pyrimidinone (Compound 223)
Step A: Preparation of 1-cyclopropyl-3-(1,6-dihydro-6-oxo-1,2-diphenyl-5-pyrimidinyl)-1,3-propanedione

To a mixture of 1,6-dihydro-6-oxo-1,2-diphenyl-5-pyrimidinecarboxylic acid (i.e. the product from Example 1, step B) (1.84 g, 6.3 mmol) and toluene (6.3 mL) was added phosphorus pentachloride (1.31 g, 6.3 mmol) at ambient temperature. The resulting mixture was heated at reflux under a nitrogen atmosphere for 6 h. The resulting yellow solution was concentrated to give 1.53 g of the acid chloride as a yellow solid.


n-Butyllithium (2.5M solution in hexanes, 2.2 mL, 5.6 mmol) was added dropwise to a solution of N,N-diisopropylamine (0.82 mL, 5.8 mmol) and anhydrous tetrahydrofuran (8 mL) at −78° C. under a nitrogen atmosphere. The resulting solution was warmed to 0° C., stirred for 30 min, and then cooled to −78° C. Cyclopropyl methyl ketone (0.55 mL, 5.6 mmol) was added dropwise at below −65° C. The resulting solution was stirred at −78° C. for 30 min and was then treated with a slurry of the acid chloride as prepared above (823 mg, 2.7 mmol) in anhydrous tetrahydrofuran (5 mL) added dropwise via syringe at below 60° C. Additional anhydrous tetrahydrofuran (5 mL) was used to complete the transfer of the acid chloride. The resulting mixture was stirred at −78° C. for 1 h and was then treated with saturated aqueous ammonium chloride (7 mL) at below −50° C. The resulting mixture was stirred at ambient temperature for 15 min and was partitioned between ethyl acetate (100 mL) and saturated aqueous ammonium chloride (50 mL). The organic layer was dried over MgSO4, filtered, and concentrated onto silica gel (2.5 g). The residue was purified by medium pressure liquid chromatography using a 24 g silica column and eluting with a gradient of 0 to 100% ethyl acetate in hexanes to provide the title compound as a pale yellow glassy solid (250 mg).



1HNMR (400 MHz, CDCl3) δ 15.88 (s, 1H), 8.93 (s, 1H), 7.40-7.33 (m, 3H), 7.33-7.26 (m, 3H), 7.24-7.19 (m, 3H), 7.14 (apparent d, 2H), 1.81 (sep, 1H), 1.20-1.15 (m, 2H), 0.99-0.92 (m, 2H).


Step B: Preparation of 1-cyclopropyl-3-(1,6-dihydro-6-oxo-1,2-diphenyl-5-pyrimidinyl)-2-(ethoxymethylene)-1,3-propanedione

A suspension of 1-cyclopropyl-3-(1,6-dihydro-6-oxo-1,2-diphenyl-5-pyrimidinyl)-1,3-propanedione (i.e. the product from Example 6, Step A) (165 mg, 0.46 mmol), triethyl orthoformate (0.23 mL, 1.4 mmol), and acetic anhydride (0.92 mL) was heated at 110° C. under a nitrogen atmosphere for 4 h. The residue was dissolved in toluene (5 mL) and the resulting solution was concentrated under reduced pressure at 50° C. The residue was re-dissolved in toluene (5 mL) and the resulting solution was concentrated at 50° C. to give 181 mg of the title compound as a brown oil that was used in the next step without further purification. 1H NMR analysis showed the product to contain a mixture of Z- and E-olefin isomers.



1HNMR (400 MHz, CDCl3) 8.63 and 8.47 (2s, 1H total), 7.68 and 7.62 (2s, 1H total), 7.33-7.16 (m, 8H), 7.10-7.02 (m, 2H), 4.27 and 4.16 (2q, 2H total), 2.64-2.57 (m, <1H), 1.42 and 1.33 (3t, 3H total), 1.11-1.06 and 1.04-0.98 (2m, 2H total), 0.91-0.82 (m, 2H).


Step C: Preparation of 5-[(5-cyclopropyl-4-isoxazolyl)carbonyl]-2,3-diphenyl-4(3H)-pyrimidinone

Anhydrous sodium acetate (68 mg, 0.83 mmol) was added to a solution of 1-cyclopropyl-3-(1,6-dihydro-6-oxo-1,2-diphenyl-5-pyrimidinyl)-2-(ethoxymethylene)-1,3-propanedione (i.e. the product from Example 6, Step B) (171 mg, 0.41 mmol) in ethanol (4 mL) at 0° C. Hydroxylamine hydrochloride (29 mg, 0.42 mmol) was added and the resulting suspension was stirred at 0° C. for 30 min and then at ambient temperature for 2 h. The resulting mixture was diluted with ethyl acetate (20 mL) and ethanol (20 mL), concentrated onto 0.8 g silica gel, and the residue purified by medium pressure liquid chromatography using a 12 g silica gel column and eluting with 0 to 100% ethyl acetate in hexanes to obtain 14 mg of the title compound, a compound of the present invention as a yellow glassy solid.



1HNMR (400 MHz, CDCl3) 8.56 (s, 1H), 8.45 (s, 1H), 7.40-7.30 (m, 6H), 7.25-7.20 (m, 2H), 7.16-7.12 (m, 2H), 3.02-2.93 (m, 1H), 1.37-1.32 (m, 2H), 1.27-1.22 (m, 2H).


EXAMPLE 7
Preparation of 5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-3-phenyl-2-(3-pyridinyl)-4(3H)-pyrimidone (Compound 113)
Step A: Preparation of N-phenyl-3-pyridinecarboximidamide

Sodium hydride (60% in mineral oil, 11.52 g, 288 mmol) was added portion-wise over 30 min to a stirred solution of 3-pyridinecarbonitrile (30 g, 288 mmol) and aniline (26 g, 290 mmol) in dimethylsulfoxide (150 mL) at 10° C. The reaction mixture was allowed to warm to ambient temperature with stirring for 18 h. The reaction mixture was slowly and cautiously poured into water containing crushed ice. The solid that precipitated was filtered, washed with petroleum ether, dissolved in dichloromethane and dried over anhydrous Na2SO4. The volatiles were removed under reduced pressure (high vacuum) and the residue was dried to afford 36.5 g of the title compound as a yellow solid.



1H NMR (CDCl3, 500 MHz) δ 9.06 (s, 1H), 8.68 (d, 1H), 8.22 (d, 1H), 7.38-7.35 (m, 3H), 7.08 (t, 1H), 6.97 (d, 2H), 5.00 (s, 2H).


Step B: Preparation of ethyl 1,6-dihydro-6-oxo-1-phenyl-2-(3-pyridinyl)-5-pyrimidinecarboxylate

A suspension of the N-phenyl-3-pyridinecarboximidamide (i.e. the product from Example 7, Step A) (36.5 g, 185 mmol) in diethyl ethoxymethylenemalonate (60 g, 280 mmol) was heated to 160° C. for 8 h. Ethanol formed in the reaction was collected using a distillation head attached to the flask containing the heated reaction mixture. The reaction mixture was then cooled to ambient temperature when the formation of a solid was observed. A mixture of diethyl ether/petroleum ether (8:2) was added to the reaction mixture was filtered. The collected solid was washed with additional ether/petroleum ether (4:1) followed by n-chlorobutane/petroleum ether (1:1) to obtain 51 g of the title compound as a light brown powder.



1H NMR (CDCl3, 500 MHz) δ 8.79 (s, 1H), 8.57 (dd, 1H), 8.52 (dd, 1H), 7.58 (dt, 1H), 7.38-7.35 (m, 3H), 7.16-7.13 (m, 3H), 4.41 (q, 2H), 1.39 (t, 3H).


Step C: Preparation of 1,6-dihydro-6-oxo-1-phenyl-2-(3-pyridinyl)-5-pyrimidinecarboxylic acid

A suspension of ethyl 1,6-dihydro-6-oxo-1-phenyl-2-(3-pyridinyl)-5-pyrimidinecarboxylate (i.e. the product from Example 7, Step B) (5.0 g, 15.5 mmol) and lithium iodide (powder, 5.2 g, 38.8 mmol) in pyridine (15 mL) was heated to 125-130° C. for 12 h. After cooling to ambient temperature, excess solvent was removed under reduced pressure. The resulting residue was dissolved in water (100 mL) and acidified with hydrochloric acid (6 N) to pH 7. The resulting dark brown solution was extracted with ethyl acetate (1×100 mL) to remove the non polar impurities. The aqueous layer was again extracted with dichloromethane/methanol (95:5) (2×50 mL). After initial extractions, the aqueous layer was slowly acidified to pH 4 and further extracted with dichloromethane/methanol (95:5) (3×50 mL). The combined neutral and acidic extracts were washed with brine and dried over anhydrous Na2SO4. The residue obtained after removal of the solvent was dried under high-vacuum to obtain 3.4 g of the title compound as a light brown solid.



1H NMR (CDCl3, 500 MHz) δ 12.67 (br s, 1H), 9.12 (s, 1H), 8.60-8.57 (m, 2H), 7.65 (dt, 1H), 7.47-7.46 (m, 3H), 7.22-7.19 (m, 3H).


Step D: Preparation of 3-oxo-1-cyclohexen-1-yl 1,6-dihydro-6-oxo-1-phenyl-2-(3-pyridinyl)-5-pyrimidinecarboxylate

To a stirred suspension of 1,6-dihydro-6-oxo-1-phenyl-2-(3-pyridinyl)-5-pyrimidinecarboxylic acid (i.e. the product from Example 7, Step C) (10.7 g, 36.3 mmol) in dichloromethane (150 mL) at ambient temperature was added 2-chloro-N-methyl pyridinium iodide (also known as the Mukaiyama reagent) (14.8 g, 57.9 mmol) followed by cyclohexanedione (6.5 g, 58 mmol) and triethylamine (9.2 g, 91 mmol). The reaction mixture was left stirring at ambient temperature overnight, then diluted with dichloromethane, washed with water, brine and dried over anhydrous Na2SO4. The residue obtained after removal of the solvent under vacuum was purified by tituration with n-chlorobutane/petroleum ether mixtures to obtain 9.8 g of the title compound as a light brown solid.



1H NMR (CDCl3, 500 MHz) δ 8.89 (s, 1H), 8.60 (d, 1H) 8.54 (dd, 1H), 7.61 (dt, 1H), 7.42-7.37 (m, 3H), 7.19-7.14 (m, 3H), 6.04 (s, 1H), 2.69-2.66 (m, 2H), 2.45-2.42 (m, 2H), 2.10 (q, 2H).


Step E: Preparation of 5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-3-phenyl-2-(3-pyridinyl)-4(3H)-pyrimidone

To a stirred solution of 3-oxo-1-cyclohexen-1-yl 1,6-dihydro-6-oxo-1-phenyl-2-(3-pyridinyl)-5-pyrimidinecarboxylate (i.e. the product from Example 7, Step D) (11.1 g, 28.6 mmol) in acetonitrile (166 mL) was added cesium fluoride (8.71 g, 57.3 mmol) followed by catalytic amount (˜50 mg) of tetrabutylammonium bromide at ambient temperature. After stirring for 3 h at ambient temperature, the reaction mixture was diluted with ethyl acetate, washed with water, brine and dried over anhydrous Na2SO4. The volatile components were removed under reduced pressure and the residue was subjected to silica gel column chromatography eluting with ethyl acetate/petroleum ether (1:1) to ethyl acetate to dichloromethane/methanol (95:5). The product obtained was washed with minimum amount of methanol to afford 1.4 g of the title compound, a compound of the present invention as a light yellow solid.



1H NMR (CDCl3, 500 MHz) mixture of tautomers δ 16.45 (s, 0.8H), 8.57-8.50 (m, 2H), 8.21 (s, 1H), 7.57 (d, 1H), 7.35 (d, 3H), 7.16-7.13 (m, 3H), 5.29 (s, 0.2H,), 2.71 (br s, 2H), 2.47 (br s, 2H), 2.04-2.02 (m, 2H).


EXAMPLE 8
Preparation of 5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-phenyl-3-(cis/trans-tetrahydro-1-oxido-2H-thiopyran-4-yl)-4(3H)-pyrimidinone (Compound 168) and 5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-phenyl-3-(trans/cis-tetrahydro-1-oxido-2H-thiopyran-4-yl)-4(3H)-pyrimidinone (Compound 169)
Step A: Preparation of 5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-phenyl-3-(cis/trans-tetrahydro-1-oxido-2H-thiopyran-4-yl)-4(3H)-pyrimidinone and 5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-phenyl-3-(trans/cis-tetrahydro-1-oxido-2H-thiopyran-4-yl)-4(3H)-pyrimidinone

To 5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-phenyl-3-(tetrahydro-2H-thiopyran-4-yl)-4(3H)-pyrimidinone (the tautomer known as 2-[[1,6-dihydro-6-oxo-2-phenyl-1-(tetrahydro-2H-thiopyran-4-yl)-5-pyrimidinyl]carbonyl]-1,3-cyclohexanedione) (0.15 g, 0.37 mmol) in a mixture of 5.0 mL water and 5.0 mL methanol at room temperature was added NaIO4 (0.074 g, 0.35 mmol). After approximately 45 min, additional NaIO4 (0.011 g, 0.05 mmol) was added and stirring was continued for an additional 2 h. The reaction mixture was extracted with dichloromethane and the combined organics were dried over MgSO4 concentrated under reduced pressure and purified by medium pressure liquid chromatography on silica gel eluting with 0 to 10% methanol in chloroform to provide 0.07 g of Compound 168 (alternatively known as 2-[[1,6-dihydro-6-oxo-2-phenyl-1-(cis/trans-tetrahydro-1-oxido-2H-thiopyran-4-yl)-5-pyrimidinyl]carbonyl]-1,3-cyclohexanedione) and and 0.03 g of Compound 169 (alternatively known as 2-[[1,6-dihydro-6-oxo-2-phenyl-1-(trans/cis-tetrahydro-1-oxido-2H-thiopyran-4-yl)-5-pyrimidinyl]carbonyl]-1,3-cyclohexanedione) both as solids.



1H NMR of Compound 168 (CDCl3) δ 16.58 (br s, 1H), 7.99 (s, 1H), 7.58 (m, 3H), 7.47 (m, 2H), 4.14 (m, 1H), 3.39 (m, 2H), 3.12 (m, 2H), 2.74 (t, 2H), 2.49 (t, 2H), 2.37 (t, 2H), 2.05 (m, 4H).



1H NMR Compound 169 (CDCl3) δ 16.42 (br s, 1H), 8.00 (s, 1H), 7.54 (m, 5H), 4.06 (m, 1H), 3.65 (m, 2H), 3.07 (m, 2H), 2.60 (br s, 4H), 2.17 (m, 2H), 2.07 (m, 2H), 1.80 (d, 2H).


EXAMPLE 9
Preparation of 2-(3,5-difluorophenyl)-5-[(2-hydroxy-4-oxobicyclo[3.2.1]oct-2-en-3-yl)carbonyl]-3-(2-methoxyethyl)-4(3H)-pyrimidinone (Compound 243)
Step A: Preparation of 3,5-difluorobenzenecarboxamidic acid ethyl ester hydrochloride (1:1)

To a stirred solution of 3,5-difluorobenzonitirile (25 g, 180 mmol) in ethanol (336 mL) and dichloromethane (180 mL) at 0° C., was added acetyl chloride (128 mL, 1800 mmol) drop wise via addition funnel. The reaction mixture was allowed to warm to room temperature and stir for 24 h. The reaction mixture was then concentrated under reduced pressure to afford a solid, which was washed with diethyl ether and dried under reduced pressure to afford the title product as a white solid (21.5 g) which was carried forward to the next step without further purification.


Step B: Preparation of 3,5-difluoro-N-(2-methoxyethyl)benzenecarboximidamide hydrochloride (1:1)

To a stirred solution of 3,5-difluorobenzenecarboxamidic acid ethyl ester hydrochloride (5.39 g, 24.3 mmol) (i.e. the product from Example 9, Step A) in methanol (25 mL) at 0° C., was added 2-methoxy-1-ethylamine (2.2 mL, 25.5 mmol). The reaction mixture was allowed to warm to room temperature and stir for 24 h. The reaction mixture was concentrated under reduced pressure to afford the title product as a gummy oil, which was used without further purification in the next step.


Step C: Preparation of ethyl 2-(3,5-difluorophenyl)-1,6-dihydro-1-(2-methoxyethyl)-6-oxo-5-pyrimidinecarboxyate

To a stirred solution of 3,5-difluoro-N-(2-methoxyethyl)benzenecarboximidamide hydrochloride (1:1 (i.e. the product from Example 9, Step B) (24.3 mmol) in ethanol (25 mL) was added diethyl ethoxymethylenemalonate (5.25 g, 24.3 mmol) followed by sodium ethoxide (21% soln) (9.1 mL, 24.3 mmol). The reaction mixture was heated and stirred at reflux for 24 h. The reaction mixture was cooled to room temperature concentrated under reduced pressure. The residue was purified by column chromatography eluting with 50% ethyl acetate in hexanes to afford the title product as a white solid (6.1 g).



1H NMR (CDCl3) δ 8.65 (s, 1H), 7.14 (m, 2H), 6.98 (m, 1H), 4.41 (m, 2H), 4.21 (m, 2H), 3.67 (m, 2H), 3.22 (s, 3H), 1.40 (m, 3H).


Step D: Preparation of 2-(3,5-difluorophenyl)-1,6-dihydro-1-(2-methoxyethyl)-6-oxo-5-pyrimidinecarboxylic acid

To a stirred solution of ethyl ethyl 2-(3,5-difluorophenyl)-1,6-dihydro-1-(2-methoxyethyl)-6-oxo-5-pyrimidinecarboxyate (i.e. the product from Example 9, Step C) (1.14 g, 3.37 mmol) in ethyl acetate (10 mL) was added lithium iodide powder (1.35 g, 10.0 mmol). The reaction mixture was heated to reflux for 24 h, cooled, and then stirred at room temperature for 72 h. The reaction mixture was concentrated under reduced pressure. To the resulting residue was added water (10 mL), followed by 6 N hydrochloric acid until the pH was 2. The mixture was extracted with dichloromethane, and the organic layer was dried (MgSO4) and concentrated under reduced pressure to afford a solid, which was washed with diethyl ether and dried under reduced pressure to afford the title product as a white solid (700 mg).



1H NMR (CDCl3) δ 12.88 (s, 1H), 8.99 (s, 1H), 7.20 (m, 2H), 7.03 (m, 1H), 4.32 (m, 2H), 3.69 (m, 2H), 3.25 (s, 3H).


Step E: Preparation of 2-(3,5-difluorophenyl)-5-[(2-hydroxy-4-oxobicyclo[3.2.1]oct-2-en-3-yl)carbonyl]-3-(2-methoxyethyl)-4(3H)-pyrimidinone

To 2-(3,5-difluorophenyl)-1,6-dihydro-1-(2-methoxyethyl)-6-oxo-5-pyrimidinecarboxylic acid (i.e. the product from Example 9, Step D) (0.25 g, 0.81 mmol) in 10 mL of dichloromethane was added oxalyl chloride (0.21 g, 1.6 mmol) and one drop of N,N-dimethylformamide. The reaction mixture was stirred at room temperature for 2 h and then concentrated under reduced pressure. The remaining crude oil was re-dissolved in dichloromethane (10 mL) and then treated with bicycle[3.2.1]octane-2,4-dione (0.12 g, 0.88 mmol) (prepared according to U.S. Pat. No. 6,815,563) and triethylamine (0.16 g, 1.6 mmol). After 30 min at room temperature, a catalytic amount of 2-hydroxy-2-methyl-propanenitrile (0.0075 g, 0.088 mmol) and triethylamine (0.16 g, 1.6 mmol) were added and the reaction mixture was stirred at ambient temperature over night. The reaction mixture was then concentrated under reduced pressure and purified by medium pressure liquid chromatography on silica gel eluting with 0 to 10% methanol in chloroform to provide 0.180 g of the title compound (also known as 3-[[2-(3,5-difluorophenyl)-1,6-dihydro-1-(2-methoxyethyl)-6-oxo-5-pyrimidinyl]carbonyl]biciclo[3.2.1]octane-2,4-dione), a compound of the present invention, as a solid.



1H NMR (CDCl3) δ 16.58 (br s, 1H), 8.05 (s, 1H), 7.17 (m, 2H), 6.96 (m, 1H), 4.18 (br s, 2H), 3.61 (t, 2H), 3.26 (br s, 3H), 3.09 (br s, 1H), 2.96 (br s, 1H), 2.26 (d, 1H), 2.17 (br s, 2H), 2.02 (br s, 1H), 1.88 (br s, 1H), 1.73 (m, 1H).


EXAMPLE 10
Preparation of 5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-3-(2-methoxyethyl)-2-(3-thienyl)-4(3H)-pyrimidinone (Compound 97)
Step A: Preparation of 3-thiophenecarboximidic acid ethyl ester hydrochloride

To a solution of thiophene-3-carbonitrile (10 g, 9.2 mmol) in dichloromethane (100 mL) and ethanol (170 mL) at 0° C. was added acetyl chloride (114 g, 145 mmol). The reaction was allowed to slowly warm to ambient temperature and stir 16 h. The reaction mixture was then concentrated under reduced pressure to yield a solid which was triturated with diethyl ether resulting in 17.1 g of 3-thiophenecarboximidic acid ethyl ester hydrochloride as a white solid.



1H NMR (DMSO-d6) δ 11.77 (br s, 2H), 8.92 (m, 1H), 7.90 (m, 1H), 7.83 (m, 1H), 4.60 (q, 2H), 1.46 (t, 3H).


Step B: Preparation of ethyl 1,6-dihydro-1-(2-methoxyethyl)-6-oxo-2-(3-thienyl)-5-pyrimidinecarboxylate

2-Methoxy-1-ethylamine (0.86 g, 11.4 mmol) was added to a solution of 3-thiophenecarboximidic acid ethyl ester hydrochloride (2.0 g, 10.4 mmol) in methanol (10 mL), which was then stirred at ambient temperature for 1.5 h. The reaction mixture was then concentrated under reduced pressure and redissolved in ethanol (10 mL). Sodium ethoxide solution (21% w/w in ethanol, 3.4 g, 10 mmol) and diethyl ethoxymethylenemalonate (2.2 g, 10 mmol) were added and the mixture was heated to reflux for 2 h before being concentrated under reduced pressure and purified by medium pressure liquid chromatography on silica gel eluting with 0 to 100% ethyl acetate in hexanes to provide 1.82 g of the title compound as an oil.



1H NMR (CDCl3) δ 8.68 (s, 1H), 8.06 (m, 1H), 7.48 (m, 1H), 7.43 (m, 1H), 4.38 (m, 4H), 3.81 (t, 2H), 3.29 (s, 3H), 1.40 (t, 3H).


Step C: 1,6-dihydro-1-(2-methoxyethyl)-6-oxo-2-(3-thienyl)-5-pyrimidinecarboxylic acid

Ethyl 1,6-dihydro-1-(2-methoxyethyl)-6-oxo-2-(3-thienyl)-5-pyrimidinecarboxylate a (1.82 g, 5.90 mmol) (i.e. the product from Example 10, Step B) was dissolved in ethyl acetate and treated with lithium iodide (powder, 2.36 g, 17.6 mmol) and heated to reflux for 16 h. The crude reaction mixture was concentrated under reduced pressure and then aqueous sodium bicarbonate solution was added and the resulting solution was extracted with ethyl acetate which was then discarded. The aqueous layer was made acidic with hydrochloric acid (1 N) and then extracted with dichloromethane (2×40 mL). The combined organics were dried over MgSO4 and concentrated under reduced pressure to provide the title compound as a solid.



1H NMR (CDCl3) δ 12.96 (br s, 1H), 8.99 (s, 1H), 8.17 (m, 1H), 7.53 (m, 1H), 7.48 (m, 1H), 4.47 (t, 2H), 3.83 (t, 2H), 3.32 (s, 3H).


Step D: Preparation of 5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-3-(2-methoxyethyl)-2-(3-thienyl)-4(3H)-pyrimidinone

To 1,6-dihydro-1-(2-methoxyethyl)-6-oxo-2-(3-thienyl)-5-pyrimidinecarboxylic acid (i.e. the product from Example 10, Step C) (0.5 g, 1.8 mmol) in 10 mL of dichloromethane was added oxalyl chloride (0.45 g, 3.6 mmol) and one drop of N,N-dimethylformamide. The reaction mixture was stirred at room temperature for 2 h and then concentrated under reduced pressure. The crude oil was redissolved in 10 mL of dichloromethane and treated with 1,3-cyclohexanedione (0.22 g, 2.0 mmol) and triethylamine (0.18 g, 1.8 mmol). The reaction mixture was stirred for 30 min then treated with a catalytic amount of 2-hydroxy-2-methyl-propanenitrile (0.015 g, 0.18 mmol) and triethylamine (0.182 g, 1.8 mmol) and stirred at ambient temperature for 16 h. The reaction mixture was then concentrated under reduced pressure and purified by medium pressure liquid chromatography on silica gel eluting with 0 to 10% methanol in chloroform to provide 0.160 g of the title compound (also known as 2-[[1,6-dihydro-1-(2-methoxyethyl)-6-oxo-2-(3-thienyl)-5-pyrimidinyl]carbonyl]-1,3-cyclohexanedione), a compound of the invention, as a solid.



1H NMR (CDCl3) δ 16.51 (s, 1H), 8.14 (s, 1H), 7.97 (m, 1H), 7.43 (m, 2H), 4.29 (t, 2H), 3.70 (t, 2H), 3.29 (s, 3H), 2.73 (t, 2H), 2.50 (t, 2H), 2.08 (m, 2H).


EXAMPLE 11
Preparation of 3-cyclohexyl-5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-phenyl-4(3H)-pyrimidinone (Compound 128)
Step A: Preparation of ethyl 1-cyclohexyl-1,6-dihydro-6-oxo-2-phenyl-5-pyrimidinecarboxyate

Cyclohexylamine (0.58 g, 5.8 mmol) was added to a solution of ethyl benzenecarboximidic acid ethyl ester (1.0 g, 5.4 mmol) in methanol (10 mL), which was then stirred at room temperature for 16 h. The reaction mixture was then concentrated under reduced pressure and then redissolved in ethanol (10 mL). Sodium ethoxide solution (21% w/w in ethanol, 1.8 g, 5.5 mmol) and diethyl ethoxymethylenemalonate (1.2 g, 5.5 mmol) were added and the mixture was heated to reflux for 16 h before being concentrated under reduced pressure and purified by medium pressure liquid chromatography on silica gel eluting with 0 to 100% ethyl acetate in hexanes to provide 1.41 g of the title compound as a yellow oil.



1H NMR (CDCl3) δ 8.58 (s, 1H), 7.53 (m, 3H), 7.45 (m, 2H), 4.41 (m, 2H), 3.94 (m, 1H), 2.76 (m, 2H), 1.78 (d, 2H), 1.67 (d, 2H), 1.53 (d, 1H), 1.42 (m, 3H), 1.21 (m, 1H), 0.96 (m, 2H).


Step B: Preparation of 1-cyclohexyl-1,6-dihydro-6-oxo-2-phenyl-5-pyrimidinecarboxylic acid

Ethyl 1-cyclohexyl-1,6-dihydro-6-oxo-2-phenyl-5-pyrimidinecarboxyate (1.41 g, 4.32 mmol) (i.e. the product from Example 11, Step A) was dissolved in ethyl acetate and treated with lithium iodide (powder, 1.72 g, 12.8 mmol) and heated to reflux for 16 h. The crude reaction mixture was concentrated under reduced pressure and then aqueous sodium bicarbonate was added and the resulting solution was extracted with ethyl acetate which was then discarded. The aqueous layer was made acidic with hydrochloric acid (1 N) and then extracted with dichloromethane (2×40 mL). The combined organic extracts were dried over MgSO4 and concentrated under reduced pressure resulting in 0.58 g of the title product as a solid.



1H NMR (CDCl3) δ 13.30 (br. s., 1 H), 8.94 (s, 1 H), 7.59 (m, 3 H), 7.48 (m, 2 H), 4.12 (m, 1 H), 2.68 (m, 2 H), 1.84 (d, 2 H), 1.74 (d, 2 H), 1.60 (d, 1 H), 1.22 (m, 1 H), 1.03 (m, 2 H).


Step C: Preparation of 2-[(1-cyclohexyl-1,6-dihydro-6-oxo-2-phenyl-5-pyrimidinyl)carbonyl]-1,3-cyclohexanedione

To 1-cyclohexyl-1,6-dihydro-6-oxo-2-phenyl-5-pyrimidinecarboxylic acid (i.e. the product from Example 11, Step B) (0.58 g, 1.5 mmol) in 10 mL of dichloromethane was added oxalyl chloride (0.490 g, 3.9 mmol) and one drop of N,N-dimethylformamide. The reaction was stirred at ambient temperature for 2 h and then concentrated under reduced pressure. The crude oil was then redissolved in 10 mL of dichloromethane and then treated with 1,3-cyclohexanedione (0.24 g, 2.1 mmol) and triethylamine (0.39 g, 3.8 mmol) stirred for 30 min, then treated with a catalytic amount of 2-hydroxy-2-methyl-propanenitrile (0.015 g, 0.15 mmol) and triethylamine (0.393 g, 3.8 mmol) and stirred at ambient temperature for 16 h. The reaction mixture was then concentrated under reduced pressure and purified by medium pressure liquid chromatography on silica gel eluting with 0 to 10% methanol in chloroform to provide 0.570 g of the title compound, a compound of the invention, as a solid.



1H NMR (CDCl3) δ 16.61 (s, 1H), 8.02 (s, 1H), 7.50 (m, 5H), 3.93 (m, 1H), 2.73 (t, 2H), 2.61 (m, 2H), 2.51 (t, 2H), 2.08 (m, 2H), 1.74 (m, 4H), 1.51 (d, 1H), 1.19 (m, 1H), 0.97 (m, 2H).


By the procedures described herein together with methods known in the art, the following compounds of Tables 1 to 32 can be prepared. The following abbreviations are used in the Tables which follow: Me means methyl, Et means ethyl, n-Pr means normal propyl, i-Pr means isopropyl, c-Pr means cyclopropyl, n-Bu means normal butyl, i-Bu means isobutyl, s-Bu means secondary butyl, c-Bu means cyclobutyl, t-Bu means tertiary butyl, n-pent means normal pentyl, c-Pent means cyclopentyl, n-Hex means normal hexyl, hept means hetpyl, c-Hex means cyclohexyl, Ph means phenyl, OMe means methoxy, OEt means ethoxy, SMe means methylthio, SEt means ethylthio, thp means tetrahydropyran, thtp means tetrahydrothiopyran, thf means tetrahydrofuran, —CN means cyano, —NO2 means nitro, S(O)Me means methylsulfinyl, SO2 means sulfonyl and S(O)2Me means methylsulfonyl.









TABLE 1







embedded image







R1







Me


Et


n-Pr


i-Pr


c-Pr


n-Bu


i-Bu


s-Bu


c-Bu


t-Bu


n-pent


c-Pent


n-Hex


c-Hex


Ph


CH2-c-Pr


CH2-c-Bu


CH2SPh


CH2SCH3


CH2CF3


CH2Ph


Ph(4-Me)


CH2CHC(CH3)2


CH2CH2C≡CH


CH2CH═CCl2


CH2CH═CF2


CH2CF═CF2


CH2CCl═CCl2


CH2C═CCH3


CH2OCH2CH3


CH2CH2OCH3


CH2SO2CH3


CH2SCH2CH3


Ph(2,3-di-OMe)


CH2SO2-n-Pr


CH2CH2SO2Et


Ph(2,4-di-OMe)


Ph(2,5-di-OMe)


Ph(2,6-di-OMe)


Ph(3,5-di-OMe)


CH2Ph(2-OMe)


CH2Ph(3-OMe)


CH2Ph(4-OMe)


CH2CH2SMe


CH2SCH2Ph


CH2SO2Ph


CH2CH2SEt


Ph(2,4-di-Cl)


Ph(2,5-di-Cl)


Ph(2,6-di-Cl)


Ph(3,5-di-Cl)


Ph(2,3-di-Me)


Ph(2,4-di-Me)


Ph(2,5-di-Me)


Ph(2,6-di-Me)


Ph(3,5-di-Me)


CH2-c-Hex


Ph(2,3-di-F)


Ph(2,4-di-F)


Ph(2,5-di-F)


Ph(2,6-di-F)


CH2CH2CF3


CH2C≡CH


Ph(2,3-di-Cl)


Ph(3,5-di-F)


isoxazolin-2-yl


Ph(2-Cl)


Ph(3-Cl)


Ph(4-Cl)


Ph(2-Me)


Ph(3-Me)


CH2OCH3


CH2CH═CH2


Ph(2-OMe)


Ph(3-OMe)


Ph(4-OMe)


Ph(2-CN)


Ph(3-CN)


Ph(4-CN)


Ph(2-F)


Ph(3-F)


Ph(4-F)


CH2S-n-Pr


CH2-c-Pent


oxazolin-2-yl


2-pyridinyl


3-pyridinyl


4-pyridinyl


Ph(2-NO2)


Ph(3-NO2)


Ph(4-NO2)


Ph(2-CF3)


Ph(3-CF3)


Ph(4-CF3)


Ph(2-Br)


Ph(3-Br)


Ph(4-Br)


CH2Ph(2-Me)


CH2Ph(3-Me)


CH2Ph(4-Me)


CH2Ph(2-Cl)


CH2Ph(3-Cl)


CH2Ph(4-Cl)


thiazol-3-yl


thiazol-2-yl


thiazolin-2-yl


thiazol-2-yl


oxazol-2-yl


CH2CF2CF3


CH═CH2


CH2(thf-2-yl)


CH2(3-methylisoxazolin-5-yl)


isoxazolin-4-yl


CH2(3-methylisoxazol-5-yl)


5-methylisoxazol-3-yl


4-methyloxazol-2-yl


4-methylthiazol-2-yl


CH2CH2CH═CH2


CH2SO2CH2CH3


CH2CH2SO2Me


CH2OCH2OCH3


3-methylthiazol-2-yl


5-chloropyridin-2-yl


5-methylpyridin-2-yl


5-methoxypyridin-2-yl


6-methylpyridin-2-yl


6-methylpyridin-3-yl


3-methoxypyridin-4-yl


3-methylpyridin-4-yl


3-chloropyridin-4-yl


CH2OCH2CH2OCH3


CH2C(CH3)C(CH3)2


n-hept


c-hept


thp-4-yl


thtp-4-yl


Ph(2,3-di-OMe)


Ph(3,4-di-OMe)


Ph(3,4-di-Me)


Ph(3,4-di-F)


Ph(3,4,5-tri-OMe)


Ph(2-I)


Ph(3-I)


Ph(4-I)


Ph(2-Et)


Ph(3-Et)


Ph(4-Et)


CH2CH2OCH2CH3


CH(CH3)CH2OCH3


Ph(2-OCF3)


Ph(3-OCF3)


Ph(4-OCF3)


Ph(2-Me-3-F)


Ph(2-Me-4-F)


Ph(2-Me-5-F)


Ph(2-F-3-Me)


Ph(2-F-4-Me)


Ph(2-F-5-Me)


Ph(3-F-4-Me)


Ph(3-F-5-Me)


Ph(3-Me-4-F)


CH2CH2CH2OCH3


CH2CH2CH2OCH2CH3


CH2(thp-2-yl)


CH2(thp-4-yl)


CH2CH2CH═CH2


CH2C≡CH


CH2CH2SCH3


CH2CH2SOCH3


CH2CH2SO2CH3


CH2CH2CH2SCH3


CH2CH2CH2SOCH3


CH2CH2CH2SO2CH3


c-hex(3-OCH3)


c-hex(4-OCH3)


c-hex(3,4-di-OCH3)


c-hex(3,5-di-OCH3)


CH2CH2SCH3





R2 is Ph







The present disclosure also includes Tables 1A through 57A, each of which is constructed the same as Table 1 above except that the row heading in Table 1 (i.e. “R2 is Ph”) is replaced with the respective row headings shown below. For example, in Table 1A the row heading is “R2 is Me”, and R1 is as defined in Table 1 above. Thus, the first entry in Table 1A specifically discloses a compound of Formula 1 wherein X is CH; Y is C(O); R1 is Me; R2 is Me; R3 is OH; A is A-1; B1 is C-1; B2 is C-3; B3 is C-1; and each R14, R15, R18 and R19 is H. Tables 2A through 57A are constructed similarly.
















Table
Row Heading









 1A
R2 is Me



 2A
R2 is Et



 3A
R2 is n-Pr



 4A
R2 is c-Pr



 5A
R2 is SMe



 6A
R2 is SO2Me



 7A
R2 is CF3



 8A
R2 is Ph(2-Cl)



 9A
R2 is Ph(3-Cl)



10A
R2 is Ph(4-Cl)



11A
R2 is Ph(2-Me)



12A
R2 is Ph(3-Me)



13A
R2 is Ph(4-Me)



14A
R2 is Ph(2-OMe)



15A
R2 is Ph(3-OMe)



16A
R2 is Ph(4-OMe)



17A
R2 is Ph(2-F)



18A
R2 is Ph(3-F)



19A
R2 is Ph(4-F)



20A
R2 is OMe



21A
R2 is OEt



22A
R2 is CH2Ph



23A
R2 is 2-pyridinyl



24A
R2 is 3-pyridinyl



25A
R2 is 4-pyridinyl



26A
R2 is H



27A
R2 is Ph(3,5-di-F)



28A
R2 is Ph(3,4-di-F)



29A
R2 is Ph(3,4,5-tri-F)



30A
R2 is Ph(2,3-di-F)



31A
R2 is Ph(3-CF3)



32A
R2 is Ph(4-CF3)



33A
R2 is Ph(3,5-di-CF3)



34A
R2 is n-Bu



35A
R2 is CH2OCH3,



36A
R2 is CH2CH2OCH3



37A
R2 is CH2CH2CF3



38A
R2 is CH2CF3



39A
R2 is n-pent



40A
R2 is c-pent



41A
R2 is c-Hex



42A
R2 is n-Hex



43A
R2 is thp-4-yl



44A
R2 is Ph(2-CN)



45A
R2 is Ph(3-CN)



46A
R2 is Ph(4-CN)



47A
R2 is Ph(2-C≡CH)



48A
R2 is Ph(3-C≡CH)



49A
R2 is Ph(4-C≡CH)



50A
R2 is Ph(3-Me, 2-F)



51A
R2 is Ph(3-Me-4-F)



52A
R2 is Ph(3-Me, 5-F)



53A
R2 is Ph(3-Me, 6-F)



54A
R2 is Ph(3-F, 2-Me)



55A
R2 is Ph(3-F-4-Me)



56A
R2 is Ph(3-F-5-Me)



57A
R2 is Ph(3-F, 6-Me)

















TABLE 2









embedded image



















R2
R3
R14a
R15a
R18
R19
R14b
R15b





Et
OH
Me
H
H
H
H
H


CF3
OH
Me
H
H
H
H
H


n-Pr
OH
Me
H
H
H
H
H


c-Pr
OH
Me
H
H
H
H
H


Ph
OH
Me
H
H
H
H
H


Ph(2-Cl)
OH
Me
H
H
H
H
H


Ph(3-Cl)
OH
Me
H
H
H
H
H


Ph(4-Cl)
OH
Me
H
H
H
H
H


SMe
OH
Me
H
H
H
H
H


SO2Me
OH
Me
H
H
H
H
H


n-Bu
OH
Me
H
H
H
H
H


Ph(2-F)
OH
Me
H
H
H
H
H


Ph(3-F)
OH
Me
H
H
H
H
H


Ph(4-F)
OH
Me
H
H
H
H
H


Ph(3,5-di-F)
OH
Me
H
H
H
H
H


Ph(2-Me)
OH
Me
H
H
H
H
H


Ph(3-Me)
OH
Me
H
H
H
H
H


Ph(4-Me)
OH
Me
H
H
H
H
H


Ph(3,5-di-Me)
OH
Me
H
H
H
H
H


2-pyridinyl
OH
Me
H
H
H
H
H


3-pyridinyl
OH
Me
H
H
H
H
H


4-pyridinyl
OH
Me
H
H
H
H
H


Et
OH
Me
Me
H
H
H
H


CF3
OH
Me
Me
H
H
H
H


n-Pr
OH
Me
Me
H
H
H
H


c-Pr
OH
Me
Me
H
H
H
H


Ph
OH
Me
Me
H
H
H
H


Ph(2-Cl)
OH
Me
Me
H
H
H
H


Ph(3-Cl)
OH
Me
Me
H
H
H
H


Ph(4-Cl)
OH
Me
Me
H
H
H
H


SMe
OH
Me
Me
H
H
H
H


SO2Me
OH
Me
Me
H
H
H
H


Et
OH
H
H
Me
Me
H
H


CF3
OH
H
H
Me
Me
H
H


n-Pr
OH
H
H
Me
Me
H
H


c-Pr
OH
H
H
Me
Me
H
H


Ph
OH
H
H
Me
Me
H
H


Ph(2-Cl)
OH
H
H
Me
Me
H
H


Ph(3-Cl)
OH
H
H
Me
Me
H
H


Ph(4-Cl)
OH
H
H
Me
Me
H
H


SMe
OH
H
H
Me
Me
H
H


SO2Me
OH
H
H
Me
Me
H
H


n-Bu
OH
H
H
Me
Me
H
H


Ph(2-F)
OH
H
H
Me
Me
H
H


Ph(3-F)
OH
H
H
Me
Me
H
H


Ph(4-F)
OH
H
H
Me
Me
H
H


Ph(3,5-di-F)
OH
H
H
Me
Me
H
H


Ph(2-Me)
OH
H
H
Me
Me
H
H


Ph(3-Me)
OH
H
H
Me
Me
H
H


Ph(4-Me)
OH
H
H
Me
Me
H
H


Ph(3,5-di-Me)
OH
H
H
Me
Me
H
H


2-pyridinyl
OH
H
H
Me
Me
H
H


3-pyridinyl
OH
H
H
Me
Me
H
H


4-pyridinyl
OH
H
H
Me
Me
H
H


Et
OH
Me
Me
H
H
Me
Me


CF3
OH
Me
Me
H
H
Me
Me


n-Pr
OH
Me
Me
H
H
Me
Me


c-Pr
OH
Me
Me
H
H
Me
Me


Ph
OH
Me
Me
H
H
Me
Me


Ph(2-Cl)
OH
Me
Me
H
H
Me
Me


Ph(3-Cl)
OH
Me
Me
H
H
Me
Me


Ph(4-Cl)
OH
Me
Me
H
H
Me
Me


SMe
OH
Me
Me
H
H
Me
Me


SO2Me
OH
Me
Me
H
H
Me
Me


n-Bu
OH
Me
Me
H
H
Me
Me


Ph(2-F)
OH
Me
Me
H
H
Me
Me


Ph(3-F)
OH
Me
Me
H
H
Me
Me


Ph(4-F)
OH
Me
Me
H
H
Me
Me


Ph(3,5-di-F)
OH
Me
Me
H
H
Me
Me


Ph(2-Me)
OH
Me
Me
H
H
Me
Me


Ph(3-Me)
OH
Me
Me
H
H
Me
Me


Ph(4-Me)
OH
Me
Me
H
H
Me
Me


Ph(3,5-di-Me)
OH
Me
Me
H
H
Me
Me


2-pyridinyl
OH
Me
Me
H
H
Me
Me


3-pyridinyl
OH
Me
Me
H
H
Me
Me


4-pyridinyl
OH
Me
Me
H
H
Me
Me


Et
SPh
H
H
H
H
H
H


CF3
SPh
H
H
H
H
H
H


n-Pr
SPh
H
H
H
H
H
H


c-Pr
SPh
H
H
H
H
H
H


Ph
SPh
H
H
H
H
H
H


Ph(2-Cl)
SPh
H
H
H
H
H
H


Ph(3-Cl)
SPh
H
H
H
H
H
H


Ph(4-Cl)
SPh
H
H
H
H
H
H


SMe
SPh
H
H
H
H
H
H


SO2Me
SPh
H
H
H
H
H
H


n-Bu
SPh
H
H
H
H
H
H


Ph(2-F)
SPh
H
H
H
H
H
H


Ph(3-F)
SPh
H
H
H
H
H
H


Ph(4-F)
SPh
H
H
H
H
H
H


Ph(3,5-di-F)
SPh
H
H
H
H
H
H


Ph(2-Me)
SPh
H
H
H
H
H
H


Ph(3-Me)
SPh
H
H
H
H
H
H


Ph(4-Me)
SPh
H
H
H
H
H
H


Ph(3,5-di-Me)
SPh
H
H
H
H
H
H


2-pyridinyl
SPh
H
H
H
H
H
H


3-pyridinyl
SPh
H
H
H
H
H
H


4-pyridinyl
SPh
H
H
H
H
H
H


Et
OMe
H
H
H
H
H
H


CF3
OMe
H
H
H
H
H
H


n-Pr
OMe
H
H
H
H
H
H


c-Pr
OMe
H
H
H
H
H
H


Ph
OMe
H
H
H
H
H
H


Ph(2-Cl)
OMe
H
H
H
H
H
H


Ph(3-Cl)
OMe
H
H
H
H
H
H


Ph(4-Cl)
OMe
H
H
H
H
H
H


SMe
OMe
H
H
H
H
H
H


SO2Me
OMe
H
H
H
H
H
H


n-Bu
OMe
H
H
H
H
H
H


Ph(2-F)
OMe
H
H
H
H
H
H


Ph(3-F)
OMe
H
H
H
H
H
H


Ph(4-F)
OMe
H
H
H
H
H
H


Ph(3,5-di-F)
OMe
H
H
H
H
H
H


Ph(2-Me)
OMe
H
H
H
H
H
H


Ph(3-Me)
OMe
H
H
H
H
H
H


Ph(4-Me)
OMe
H
H
H
H
H
H


Ph(3,5-di-Me)
OMe
H
H
H
H
H
H


2-pyridinyl
OMe
H
H
H
H
H
H


3-pyridinyl
OMe
H
H
H
H
H
H


4-pyridinyl
OMe
H
H
H
H
H
H


Et
OSO2Ph(4-Me)
H
H
H
H
H
H


CF3
OSO2Ph(4-Me)
H
H
H
H
H
H


n-Pr
OSO2Ph(4-Me)
H
H
H
H
H
H


c-Pr
OSO2Ph(4-Me)
H
H
H
H
H
H


Ph
OSO2Ph(4-Me)
H
H
H
H
H
H


Ph(2-Cl)
OSO2Ph(4-Me)
H
H
H
H
H
H


Ph(3-Cl)
OSO2Ph(4-Me)
H
H
H
H
H
H


Ph(4-Cl)
OSO2Ph(4-Me)
H
H
H
H
H
H


SMe
OSO2Ph(4-Me)
H
H
H
H
H
H


SO2Me
OSO2Ph(4-Me)
H
H
H
H
H
H


n-Bu
OSO2Ph(4-Me)
H
H
H
H
H
H


Ph(2-F)
OSO2Ph(4-Me)
H
H
H
H
H
H


Ph(3-F)
OSO2Ph(4-Me)
H
H
H
H
H
H


Ph(4-F)
OSO2Ph(4-Me)
H
H
H
H
H
H


Ph(3,5-di-F)
OSO2Ph(4-Me)
H
H
H
H
H
H


Ph(2-Me)
OSO2Ph(4-Me)
H
H
H
H
H
H


Ph(3-Me)
OSO2Ph(4-Me)
H
H
H
H
H
H


Ph(4-Me)
OSO2Ph(4-Me)
H
H
H
H
H
H


Ph(3,5-di-Me)
OSO2Ph(4-Me)
H
H
H
H
H
H


2-pyridinyl
OSO2Ph(4-Me)
H
H
H
H
H
H


3-pyridinyl
OSO2Ph(4-Me)
H
H
H
H
H
H


4-pyridinyl
OSO2Ph(4-Me)
H
H
H
H
H
H













Et
OH
Me
Me
—C(O)—
Me
Me


CF3
OH
Me
Me
—C(O)—
Me
Me


n-Pr
OH
Me
Me
—C(O)—
Me
Me


c-Pr
OH
Me
Me
—C(O)—
Me
Me


Ph
OH
Me
Me
—C(O)—
Me
Me


Ph(2-Cl)
OH
Me
Me
—C(O)—
Me
Me


Ph(3-Cl)
OH
Me
Me
—C(O)—
Me
Me


Ph(4-Cl)
OH
Me
Me
—C(O)—
Me
Me


SMe
OH
Me
Me
—C(O)—
Me
Me


SO2Me
OH
Me
Me
—C(O)—
Me
Me


n-Bu
OH
Me
Me
—C(O)—
Me
Me


Ph(2-F)
OH
Me
Me
—C(O)—
Me
Me


Ph(3-F)
OH
Me
Me
—C(O)—
Me
Me


Ph(4-F)
OH
Me
Me
—C(O)—
Me
Me


Ph(3,5-di-F)
OH
Me
Me
—C(O)—
Me
Me


Ph(2-Me)
OH
Me
Me
—C(O)—
Me
Me


Ph(3-Me)
OH
Me
Me
—C(O)—
Me
Me


Ph(4-Me)
OH
Me
Me
—C(O)—
Me
Me


Ph(3,5-di-Me)
OH
Me
Me
—C(O)—
Me
Me


2-pyridinyl
OH
Me
Me
—C(O)—
Me
Me


3-pyridinyl
OH
Me
M
—C(O)—
Me
Me


4-pyridinyl
OH
Me
Me
—C(O)—
Me
Me





R1 is Me







The present disclosure also includes Tables 1B through 38B, each of which is constructed the same as Table 2 above except that the row heading in Table 2 (i.e. “R1 is Me”) is replaced with the respective row headings shown below. For example, in Table 1B the row heading is “R1 is Et”, and R2, R3, R14a, R15a, R18, R19, R14b and R15b are as defined in Table 2 above. Thus, the first entry in Table 1B specifically discloses a compound of Formula 1 wherein X is CH; Y is C(O); R1 is Et; R2 is Et, R3 is OH; A is A-1; B1 is C-1, B2 is C-3 and B3 is C-1; R14a is Me; R15a is H; R18 is H; R19 is H; R14b is H; and R15b is H. Tables 2B through 38B are constructed similarly.
















Table
Row Heading









 1B
R1 is Et



 2B
R1 is CH2CF3



 3B
R1 is CH2CH═CH2



 4B
R1 is CH2C≡CH



 5B
R1 is Ph



 6B
R1 is Ph(2-Me)



 7B
R1 is Ph(4-Me)



 8B
R1 is Ph(2-Cl)



 9B
R1 is Ph(3-Cl)



10B
R1 is n-Pr



11B
R1 is c-Pr



12B
R1 is n-Bu



13B
R1 is i-Bu



14B
R1 is n-pent



15B
R1 is n-Hex



16B
R1 is thp-4-yl



17B
R1 is thtp-4yl



18B
R1 is c-Hex



19B
R1 is CH2CH2OCH3



20B
R1 is CH2CH2OCH2CH3



21B
R1 is CH2CH2CH2OCH3



22B
R1 is CH2CH2CH2OCH2CH3



23B
R1 is Ph(3-OMe)



24B
R1 is Ph(4-OMe)



25B
R1 is Ph(3,4-di-OMe)



26B
R1 is Ph(2-F)



27B
R1 is Ph(3-F)



28B
R1 is Ph(4-F)



29B
R1 is Ph(3-Me)



30B
R1 is Ph(2-Me-3-F)



31B
R1 is Ph(2-Me-4-F)



32B
R1 is Ph(2-Me-5-F)



33B
R1 is Ph(2-F-3-Me)



34B
R1 is Ph(2-F-4-Me)



35B
R1 is Ph(2-F-5-Me)



36B
R1 is Ph(3-F-4-Me)



37B
R1 is Ph(3-F-5-Me)



38B
R1 is Ph(3-Me-4-F)

















TABLE 3









embedded image















R2
R2







Et
Ph(2-Cl)



n-Pr
Ph(3-Cl)



c-Pr
Ph(4-Cl)



CF3
Ph(3-F)



SMe
Ph(3,5-di-F)



Ph
Ph(3-Me)







R1 is CH3, R9 CH3







The present disclosure also includes Tables 1C through 37C, each of which is constructed the same as Table 3 above except that the row heading in Table 3 (i.e. “R1 is CH3, R9 is CH3”) is replaced with the respective row headings shown below. For example, in Table 1C the row heading is “R1 is CH2CH3, R9 is CH3”, and R2 is as defined in Table 3 above. Thus, the first entry in Table 1C specifically discloses a compound of Formula 1 wherein X is CH; Y is C(O); R1 is CH2CH3; R2 is Et; A is A-5; R3 is OH; R9 is CH3; and R10 is H. Tables 2C through 27C are constructed similarly.
















Table
Row Heading









 1C
R1 is CH2CH3, R9 is CH3



 2C
R1 is CH2CH═CH2, R9 is CH3



 3C
R1 is CH2C≡CH, R9 is CH3



 4C
R1 is Ph, R9 is CH3



 5C
R1 is Ph(2-Me), R9 is CH3



 6C
R1 is Ph(4-Me), R9 is CH3



 7C
R1 is Ph(2-Me), R9 is CH3



 8C
R1 is Ph(3-Cl), R9 is CH3



 9C
R1 is CH3, R9 is CH2CH3



10C
R1 is CH2CH3, R9 is CH2CH3



11C
R1 is CH2CH═CH2, R9 is CH2CH3



12C
R1 is CH2C≡CH, R9 is CH2CH3



13C
R1 is Ph, R9 is CH2CH3



14C
R1 is Ph(2-Me), R9 is CH2CH3



15C
R1 is Ph(4-Me), R9 is CH2CH3



16C
R1 is Ph(2-Cl), R9 is CH2CH3



17C
R1 is Ph(3-Cl), R9 is CH2CH3



18C
R1 is n-Bu, R9 is CH3



19C
R1 is n-pent, R9 is CH3



20C
R1 is n-Hex, R9 is CH3



21C
R1 is thp-4-yl, R9 is CH3



22C
R1 is thtp-4-yl, R9 is CH3



23C
R1 is c-Hex, R9 is CH3



24C
R1 is CH2CH2OCH3, R9 is CH3



25C
R1 is CH2CH2OCH2CH3, R9 is CH3



26C
R1 is CH2CH2CH2OCH3, R9 is CH3



27C
R1 is CH2CH2CH2OEt, R9 is CH3



28C
R1 is n-Bu, R9 is CH2CH3



29C
R1 is n-pent, R9 is CH2CH3



30C
R1 is n-Hex, R9 is CH2CH3



31C
R1 is thp-4-yl, R9 is CH2CH3



32C
R1 is thtp-4-yl, R9 is CH2CH3



33C
R1 is c-Hex, R9 is CH2CH3



34C
R1 is CH2CH2OCH3, R9 is CH2CH3



35C
R1 is CH2CH2OCH2CH3, R9 is CH2CH3



36C
R1 is CH2CH2CH2OCH3, R9 is CH2CH3



37C
R1 is CH2CH2CH2OEt, R9 is CH2CH3

















TABLE 4









embedded image















R2
R2







Et
Ph(2-Cl)



n-Pr
Ph(3-Cl)



c-Pr
Ph(4-Cl)



CF3
Ph(3-F)



SMe
Ph(3,5-di-F)



Ph
Ph(3-Me)







R1 is CH3, R9 is CH3







The present disclosure also includes Tables 1D through 37D, each of which is constructed the same as Table 4 above except that the row heading in Table 4 (i.e. “R1 is CH3, R9 is CH3”) is replaced with the respective row headings shown below. For example, in Table 1D the row heading is “R1 is CH2CH3, R9 is CH3”, and R2 is as defined in Table 4 above. Thus, the first entry in Table 1D specifically discloses a compound of Formula 1 wherein X is CH; Y is C(O); R1 is CH2CH3; R2 is Et; A is A-5; R3 is OH; R9 is CH3; and R10 is CH3. Tables 2D through 37D are constructed similarly.













Table
Row Heading







 1D
R1 is CH2CH3, R9 is CH3


 2D
R1 is CH2CH═CH2, R9 is CH3


 3D
R1 is CH2C≡CH, R9 is CH3


 4D
R1 is Ph, R9 is CH3


 5D
R1 is Ph(2-Me), R9 is CH3


 6D
R1 is Ph(4-Me), R9 is CH3


 7D
R1 is Ph(2-Me), R9 is CH3 R5 is CH3


 8D
R1 is Ph(3-Cl), R9 is CH3


 9D
R1 is CH3, R9 is CH2CH3


10D
R1 is CH2CH3, R9 is CH2CH3


11D
R1 is CH2CH═CH2, R9 is CH2CH3


12D
R1 is CH2C≡CH, R9 is CH2CH3


13D
R1 is Ph, R9 is CH2CH3


14D
R1 is Ph(2-Me), R9 is CH2CH3


15D
R1 is Ph(4-Me), R9 is CH2CH3


16D
R1 is Ph(2-Cl), R9 is CH2CH3


17D
R1 is Ph(3-Cl), R9 is CH2CH3


18D
R1 is n-Bu, R9 is CH3


19D
R1 is n-pent, R9 is CH3


20D
R1 is n-Hex, R9 is CH3


21D
R1 is thp-4-yl, R9 is CH3


22D
R1 is thtp-4-yl, R9 is CH3


23D
R1 is c-Hex, R9 is CH3


24D
R1 is CH2CH2OCH3, R9 is CH3


25D
R1 is CH2CH2OCH2CH3, R9 is CH3


26D
R1 is CH2CH2CH2OCH3, R9 is CH3


27D
R1 is CH2CH2CH2OEt, R9 is CH3


28D
R1 is n-Bu, R9 is CH2CH3


29D
R1 is n-pent, R9 is CH2CH3


30D
R1 is n-Hex, R9 is CH2CH3


31D
R1 is thp-4-yl, R9 is CH2CH3


32D
R1 is thtp-4-yl, R9 is CH2CH3


33D
R1 is c-Hex, R9 is CH2CH3


34D
R1 is CH2CH2OCH3, R9 is CH2CH3


35D
R1 is CH2CH2OCH2CH3, R9 is CH2CH3


36D
R1 is CH2CH2CH2OCH3, R9 is CH2CH3


37D
R1 is CH2CH2CH2OEt, R9 is CH2CH3
















TABLE 5









embedded image















R1
R1







Me
Ph



Et
CH2-c-Pr



n-Pr
CH2-c-Bu



i-Pr
CH2SPh



c-Pr
CH2SCH3



n-Bu
CH2CF3



i-Bu
CH2Ph



s-Bu
Ph(4-Me)



c-Bu
CH2CHC(CH3)2



t-Bu
CH2CH2C≡CH



n-pent
CH2CH═CCl2



c-Pent
CH2CH═CF2



n-Hex
CH2CF═CF2



c-Hex
CH2CCl═CCl2



CH2C≡CCH3
isoxazolin-2-yl



CH2OCH2CH3
Ph(2-Cl)



CH2CH2OCH3
Ph(3 -Cl)



CH2SO2CH3
Ph(4-Cl)



CH2SCH2CH3
Ph(2-Me)



Ph(2,3-di-OMe)
Ph(3-Me)



CH2SO2-n-Pr
CH2OCH3



CH2CH2SO2Et
CH2CH═CH2



Ph(2,4-di-OMe)
Ph(2-OMe)



Ph(2,5-di-OMe)
Ph(3-OMe)



Ph(2,6-di-OMe)
Ph(4-OMe)



Ph(3,5-di-OMe)
Ph(2-CN)



CH2Ph(2-OMe)
Ph(3-CN)



CH2Ph(3-OMe)
Ph(4-CN)



CH2Ph(4-OMe)
Ph(2-F)



CH2CH2SMe
Ph(3-F)



CH2SCH2Ph
Ph(4-F)



CH2SO2Ph
CH2S-n-Pr



CH2CH2SEt
CH2-c-Pent



Ph(2,4-di-Cl)
oxazolin-2-yl



Ph(2,5-di-Cl)
2-pyridinyl



Ph(2,6-di-Cl)
3-pyridinyl



Ph(3,5-di-Cl)
4-pyridinyl



Ph(2,3-di-Me)
Ph(2-NO2)



Ph(2,4-di-Me)
Ph(3-NO2)



Ph(2,5-di-Me)
Ph(4-NO2)



Ph(2,6-di-Me)
Ph(2-CF3)



Ph(3,5-di-Me)
Ph(3-CF3)



CH2-c-Hex
Ph(4-CF3)



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



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



Ph(2,5-di-F)
Ph(4-Br)



Ph(2,6-di-F)
CH2Ph(2-Me)



CH2CH2CF3
CH2Ph(3-Me)



CH2C≡CH
CH2Ph(4-Me)



Ph(2,3-di-Cl)
CH2Ph(2-Cl)



Ph(3,5-di-F)
CH2Ph(3-Cl)



CH2Ph(4-Cl)
Ph(3,4-di-F)



thiazol-3-yl
Ph(3,4,5-tri-OMe)



thiazol-2-yl
Ph(2-I)



thiazolin-2-yl
Ph(3-I)



thiazol-2-yl
Ph(4-I)



oxazol-2-yl
Ph(2-Et)



CH2CF2CF3
Ph(3-Et)



CH═CH2
Ph(4-Et)



CH2(thf-2-yl)
CH2CH2OCH2CH3



CH2(3-methylisoxazolin-5-yl)
CH(CH3)CH2OCH3



isoxazolin-4-yl
Ph(2-OCF3)



CH2(3-methylisoxazol-5-yl)
Ph(3-OCF3)



5-methylisoxazol-3-yl
Ph(4-OCF3)



4-methyloxazol-2-yl
Ph(2-Me-3-F)



4-methylthiazol-2-yl
Ph(2-Me-4-F)



CH2CH2CH═CH2
Ph(2-Me-5-F)



CH2SO2CH2CH3
Ph(2-F-3-Me)



CH2CH2SO2Me
Ph(2-F-4-Me)



CH2OCH2OCH3
Ph(2-F-5-Me)



3-methylthiazol-2-yl
Ph(3-F-4-Me)



5-chloropyridin-2-yl
Ph(3-F-5-Me)



5-methylpyridin-2-yl
Ph(3-Me-4-F)



5-methoxypyridin-2-yl
CH2CH2CH2OCH3



6-methylpyridin-2-yl
CH2CH2CH2OCH2CH3



6-methylpyridin-3-yl
CH2(thp-2-yl)



3-methoxypyridin-4-yl
CH2(thp-4-yl)



3-methylpyridin-4-yl
CH2CH2CH═CH2



3-chloropyridin-4-yl
CH2C≡CH



CH2OCH2CH2OCH3
CH2CH2SCH3



CH2C(CH3)C(CH3)2
CH2CH2SOCH3



n-hept
CH2CH2SO2CH3



c-hept
CH2CH2CH2SCH3



thp-4-yl
CH2CH2CH2SOCH3



thtp-4-yl
CH2CH2CH2SO2CH3



Ph(2,3-di-OMe)
c-hex(3-OCH3)



Ph(3,4-di-OMe)
c-hex(4-OCH3)



Ph(3,4-di-Me)
c-hex(3,4-di-OCH3)



c-hex(3,5-di-OCH3)
CH2CH2SCH3







R2 is Ph







The present disclosure also includes Tables 1E through 57E, each of which is constructed the same as Table 1 above except that the row heading in Table 1 (i.e. “R2 is Ph”) is replaced with the respective row headings shown below. For example, in Table 1E the row heading is “R2 is Me”, and R1 is as defined in Table 5 above. Thus, the first entry in Table 1E specifically discloses a compound of Formula 1 wherein X is CH; Y is C(O); R1 is Me; R2 is Me; R3 is OH; A is A-1; B1 is C-1; B2 is C-3; B3 is C-1; and each R14, R15, R18 and R19 is H. Tables 2E through 57E are constructed similarly.













Table
Row Heading







 1E
R2 is Me


 2E
R2 is Et


 3E
R2 is n-Pr


 4E
R2 is c-Pr


 5E
R2 is SMe


 6E
R2 is SO2Me


 7E
R2 is CF3


 8E
R2 is Ph(2-Cl)


 9E
R2 is Ph(3-Cl)


10E
R2 is Ph(4-Cl)


11E
R2 is Ph(2-Me)


12E
R2 is Ph(3-Me)


13E
R2 is Ph(4-Me)


14E
R2 is Ph(2-OMe)


15E
R2 is Ph(3-OMe)


16E
R2 is Ph(4-OMe)


17E
R2 is Ph(2-F)


18E
R2 is Ph(3-F)


19E
R2 is Ph(4-F)


20E
R2 is OMe


21E
R2 is OEt


22E
R2 is CH2Ph


23E
R2 is 2-pyridinyl


24E
R2 is 3-pyridinyl


25E
R2 is 4-pyridinyl


26E
R2 is H


27E
R2 is Ph(3,5-di-F)


28E
R2 is Ph(3,4-di-F)


29E
R2 is Ph(3,4,5-tri-F)


30E
R2 is Ph(2,3-di-F)


31E
R2 is Ph(3-CF3)


32E
R2 is Ph(4-CF3)


33E
R2 is Ph(3,5-di-CF3)


34E
R2 is n-Bu


35E
R2 is CH2OCH3


36E
R2 is CH2CH2OCH3


37E
R2 is CH2CH2CF3


38E
R2 is CH2CF3


39E
R2 is n-pent


40E
R2 is c-pent


41E
R2 is c-Hex


42E
R2 is n-Hex


43E
R2 is thp-4-yl


44E
R2 is Ph(2-CN)


45E
R2 is Ph(3-CN)


46E
R2 is Ph(4-CN)


47E
R2 is Ph(2-C≡CH)


48E
R2 is Ph(3-C≡CH)


49E
R2 is Ph(4-C≡CH)


50E
R2 is Ph(3-Me, 2-F)


51E
R2 is Ph(3-Me-4-F)


52E
R2 is Ph(3-Me, 5-F)


53E
R2 is Ph(3-Me, 6-F)


54E
R2 is Ph(3-F, 2-Me)


55E
R2 is Ph(3-F-4-Me)


56E
R2 is Ph(3-F-5-Me)


57E
R2 is Ph(3-F, 6-Me)
















TABLE 6









embedded image















R2
R3






Et
OMe



n-Pr
OMe



c-Pr
OMe



CF3
OMe



SMe
OMe



Ph
OMe



Ph(3-F)
OMe



Ph(3,5-di-F)
OMe



Ph(3-Me)
OMe



Et
SPh



n-Pr
SPh



c-Pr
SPh



CF3
SPh



SMe
SPh



Ph
SPh



Ph(3-F)
SPh



Ph(3,5-di-F)
SPh



Ph(3-Me)
SPh



Et
OSO2Ph



n-Pr
OSO2Ph



c-Pr
OSO2Ph



CF3
OSO2Ph



SMe
OSO2Ph



Ph
OSO2Ph



Ph(3-F)
OSO2Ph



Ph(3,5-di-F)
OSO2Ph



Ph(3-Me)
OSO2Ph



Et
OC(O)Ph



n-Pr
OC(O)Ph



c-Pr
OC(O)Ph



CF3
OC(O)Ph



SMe
OC(O)Ph



Ph
OC(O)Ph



Et
OC(O)Ph



Ph(3-F)
OC(O)Ph



Ph(3,5-di-F)
OC(O)Ph



Ph(3-Me)
OC(O)Ph



n-Pr
OC(O)CH3



c-Pr
OC(O)CH3



CF3
OC(O)CH3



SMe
OC(O)CH3



Ph
OC(O)CH3



Ph(3-F)
OC(O)CH3



Ph(3,5-di-F)
OC(O)CH3



Ph(3-Me)
OC(O)CH3





R1 is phenyl







The present disclosure also includes Tables 1F through 11F, each of which is constructed the same as Table 6 above except that the row heading in Table 6 (i.e. “R1 is Ph”) is replaced with the respective row headings shown below. For example, in Table 1F the row heading is “R1 is n-Pr”, and R2 is as defined in Table 6 above. Thus, the first entry in Table 1F specifically discloses a compound of Formula 1 wherein X is CH; Y is C(O); R1 is phenyl; R2 n-Pr; R3 is OMe; A is A-3; B2 is C-3; T is —CH2CH2—; R18 and R19 are both H. Tables 2F through 11F are constructed similarly.













Table
Row Heading







 1F
R1 is n-Pr


 2F
R1 is n-Bu


 3F
R1 is n-pent


 4F
R1 is n-Hex


 5F
R1 is thp-4-yl


 6F
R1 is thtp-4-yl


 7F
R1 is c-Hex


 8F
R1 is CH2CH2OCH3


 9F
R1 is CH2CH2OCH2CH3


10F
R1 is CH2CH2CH2OCH3


11F
R1 is CH2CH2CH2OCH2CH3
















TABLE 7







embedded image







R2







Et


Ph(2-Me)


n-Pr


Ph(3-Cl)


c-Pr


Ph(4-Cl)


CF3


Ph(2-Me)


SMe


Ph(3-Me)


Ph


Ph(4-Me)
















TABLE 8









embedded image















R1
R2






CH3
Et



CH3
n-Pr



CH3
c-Pr



CH3
CF3



CH3
SMe



CH3
Ph



CH3
Ph(2-Cl)



CH3
Ph(3-Cl)



CH3
Ph(4-Cl)



CH3
Ph(3-F)



CH3
Ph(3,5-di-F)



CH3
Ph(3-Me)



Et
Et



Et
n-Pr



Et
c-Pr



Et
CF3



Et
SMe



Et
Ph



Et
Ph(2-Cl)



Et
Ph(3-Cl)



Et
Ph(4-Cl)



Et
Ph(3-F)



Et
Ph(3,5-di-F)



Et
Ph(3-Me)



CH2CH═CH2
Et



CH2CH═CH2
n-Pr



CH2CH═CH2
c-Pr



CH2CH═CH2
CF3



CH2CH═CH2
SMe



CH2CH═CH2
Ph



CH2CH═CH2
Ph(2-Cl)



CH2CH═CH2
Ph(3-Cl)



CH2CH═CH2
Ph(4-Cl)



CH2CH═CH2
Ph(3-F)



CH2CH═CH2
Ph(3,5-di-F)



CH2CH═CH2
Ph(3-Me)



CH2C≡CH
Et



CH2C≡CH
n-Pr



CH2C≡CH
c-Pr



CH2C≡CH
CF3



CH2C≡CH
SMe



CH2C≡CH
Ph



CH2C≡CH
Ph(2-Cl)



CH2C≡CH
Ph(3-Cl)



CH2C≡CH
Ph(4-Cl)



CH2C≡CH
Ph(3-F)



CH2C≡CH
Ph(3,5-di-F)



CH2C≡CH
Ph(3-Me)



Ph
Et



Ph
n-Pr



Ph
c-Pr



Ph
CF3



Ph
SMe



Ph
Ph



Ph
Ph(2-Cl)



Ph
Ph(3-Cl)



Ph
Ph(4-Cl)



Ph
Ph(3-F)



Ph
Ph(3,5-di-F)



Ph
Ph(3-Me)



Ph(2-Me)
Et



Ph(2-Me)
n-Pr



Ph(2-Me)
c-Pr



Ph(2-Me)
CF3



Ph(2-Me)
SMe



Ph(2-Me)
Ph



Ph(2-Me)
Ph(2-Cl)



Ph(2-Me)
Ph(3-Cl)



Ph(2-Me)
Ph(4-Cl)



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



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



Ph(2-Me)
Ph(3-Me)



Ph(4-Me)
Et



Ph(4-Me)
n-Pr



Ph(4-Me)
c-Pr



Ph(4-Me)
CF3



Ph(4-Me)
SMe



Ph(4-Me)
Ph



Ph(4-Me)
Ph(2-Cl)



Ph(4-Me)
Ph(3-Cl)



Ph(4-Me)
Ph(4-Cl)



Ph(4-Me)
Ph(3-F)



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



Ph(4-Me)
Ph(3-Me)



Ph(2-Cl)
Et



Ph(2-Cl)
n-Pr



Ph(2-Cl)
c-Pr



Ph(2-Cl)
CF3



Ph(2-Cl)
SMe



Ph(2-Cl)
Ph



Ph(2-Cl)
Ph(2-Cl)



Ph(2-Cl)
Ph(3-Cl)



Ph(2-Cl)
Ph(4-Cl)



Ph(2-Cl)
Ph(3-F)



Ph(2-Cl)
Ph(3,5-di-F)



Ph(2-Cl)
Ph(3-Me)



Ph(3-Cl)
Et



Ph(3-Cl)
n-Pr



Ph(3-Cl)
c-Pr



Ph(3-Cl)
CF3



Ph(3-Cl)
SMe



Ph(3-Cl)
Ph



Ph(3-Cl)
Ph(2-Cl)



Ph(3-Cl)
Ph(3-Cl)



Ph(3-Cl)
Ph(4-Cl)



Ph(3-Cl)
Ph(3-F)



Ph(3-Cl)
Ph(3,5-di-F)



Ph(3-Cl)
Ph(3-Me)



n-Pr
Et



n-Pr
n-Pr



n-Pr
c-Pr



n-Pr
CF3



n-Pr
SMe



n-Pr
Ph



n-Pr
Ph(2-Cl)



n-Pr
Ph(3-Cl)



n-Pr
Ph(4-Cl)



n-Pr
Ph(3-F)



n-Pr
Ph(3,5-di-F)



n-Pr
Ph(3-Me)



c-Pr
Et



c-Pr
n-Pr



c-Pr
c-Pr



c-Pr
CF3



c-Pr
SMe



c-Pr
Ph



c-Pr
Ph(2-Cl)



c-Pr
Ph(3-Cl)



c-Pr
Ph(4-Cl)



c-Pr
Ph(3-F)



c-Pr
Ph(3,5-di-F)



c-Pr
Ph(3-Me)



n-Bu
Et



n-Bu
n-Pr



n-Bu
c-Pr



n-Bu
CF3



n-Bu
SMe



n-Bu
Ph



n-Bu
Ph(2-Cl)



n-Bu
Ph(3-Cl)



n-Bu
Ph(4-Cl)



n-Bu
Ph(3-F)



n-Bu
Ph(3,5-di-F)



n-Bu
Ph(3-Me)



n-pent
Et



n-pent
n-Pr



n-pent
c-Pr



n-pent
CF3



n-pent
SMe



n-pent
Ph



n-pent
Ph(2-Cl)



n-pent
Ph(3-Cl)



n-pent
Ph(4-Cl)



n-pent
Ph(3-F)



n-pent
Ph(3,5-di-F)



n-pent
Ph(3-Me)



n-Hex
Et



n-Hex
n-Pr



n-Hex
c-Pr



n-Hex
CF3



n-Hex
SMe



n-Hex
Ph



n-Hex
Ph(2-Cl)



n-Hex
Ph(3-Cl)



n-Hex
Ph(4-Cl)



n-Hex
Ph(3-F)



n-Hex
Ph(3,5-di-F)



n-Hex
Ph(3-Me)



thp-4-yl
Et



thp-4-yl
n-Pr



thp-4-yl
c-Pr



thp-4-yl
CF3



thp-4-yl
SMe



thp-4-yl
Ph



thp-4-yl
Ph(2-Cl)



thp-4-yl
Ph(3-Cl)



thp-4-yl
Ph(4-Cl)



thp-4-yl
Ph(3-F)



thp-4-yl
Ph(3,5-di-F)



thp-4-yl
Ph(3-Me)



c-Hex
Et



c-Hex
n-Pr



c-Hex
c-Pr



c-Hex
CF3



c-Hex
SMe



c-Hex
Ph



c-Hex
Ph(2-Cl)



c-Hex
Ph(3-Cl)



c-Hex
Ph(4-Cl)



c-Hex
Ph(3-F)



c-Hex
Ph(3,5-di-F)



c-Hex
Ph(3-Me)



CH2CH2OCH3
Et



CH2CH2OCH3
n-Pr



CH2CH2OCH3
c-Pr



CH2CH2OCH3
CF3



CH2CH2OCH3
SMe



CH2CH2OCH3
Ph



CH2CH2OCH3
Ph(2-Cl)



CH2CH2OCH3
Ph(3-Cl)



CH2CH2OCH3
Ph(4-Cl)



CH2CH2OCH3
Ph(3-F)



CH2CH2OCH3
Ph(3,5-di-F)



CH2CH2OCH3
Ph(3-Me)



CH2CH2OCH2CH3
Et



CH2CH2OCH2CH3
n-Pr



CH2CH2OCH2CH3
c-Pr



CH2CH2OCH2CH3
CF3



CH2CH2OCH2CH3
SMe



CH2CH2OCH2CH3
Ph



CH2CH2OCH2CH3
Ph(2-Cl)



CH2CH2OCH2CH3
Ph(3-Cl)



CH2CH2OCH2CH3
Ph(4-Cl)



CH2CH2OCH2CH3
Ph(3-F)



CH2CH2OCH2CH3
Ph(3,5-di-F)



CH2CH2OCH2CH3
Ph(3-Me)



CH2CH2CH2OCH3
Et



CH2CH2CH2OCH3
n-Pr



CH2CH2CH2OCH3
c-Pr



CH2CH2CH2OCH3
CF3



CH2CH2CH2OCH3
SMe



CH2CH2CH2OCH3
Ph



CH2CH2CH2OCH3
Ph(2-Cl)



CH2CH2CH2OCH3
Ph(3-Cl)



CH2CH2CH2OCH3
Ph(4-Cl)



CH2CH2CH2OCH3
Ph(3-F)



CH2CH2CH2OCH3
Ph(3,5-di-F)



CH2CH2CH2OCH3
Ph(3-Me)



CH2CH2CH2OEt
Et



CH2CH2CH2OEt
n-Pr



CH2CH2CH2OEt
c-Pr



CH2CH2CH2OEt
CF3



CH2CH2CH2OEt
SMe



CH2CH2CH2OEt
Ph



CH2CH2CH2OEt
Ph(2-Cl)



CH2CH2CH2OEt
Ph(3-Cl)



CH2CH2CH2OEt
Ph(4-Cl)



CH2CH2CH2OEt
Ph(3-F)



CH2CH2CH2OEt
Ph(3,5-di-F)



CH2CH2CH2OEt
Ph(3-Me)





R12 is c-Pr







The present disclosure also includes Tables 1H through 2H, each of which is constructed the same as Table 8 above except that the row heading in Table 8 (i.e. “R12 is c-Pr”) is replaced with the respective row headings shown below. For example, in Table 1H the row heading is “R12 is CH3”, and R1 and R2 are as defined in Table 8 above. Thus, the first entry in Table 1H specifically discloses a compound of Formula 1 wherein X is CH; Y is C(O); R1 is CH3; R2 is Et; A is A-6; R11 is H; and R12 is CH3. Table 2H is constructed similarly.













Table
Row Heading







1H
R12 is CH3


2H
R12 is CH2CH3
















TABLE 9









embedded image















R1
R2






CH3
Et



CH3
n-Pr



CH3
c-Pr



CH3
CF3



CH3
SMe



CH3
Ph



CH3
Ph(2-Cl)



CH3
Ph(3-Cl)



CH3
Ph(4-Cl)



CH3
Ph(3-F)



CH3
Ph(3,5-di-F)



CH3
Ph(3-Me)



Et
Et



Et
n-Pr



Et
c-Pr



Et
CF3



Et
SMe



Et
Ph



Et
Ph(2-Cl)



Et
Ph(3-Cl)



Et
Ph(4-Cl)



Et
Ph(3-F)



Et
Ph(3,5-di-F)



Et
Ph(3-Me)



CH2CH═CH2
Et



CH2CH═CH2
n-Pr



CH2CH═CH2
c-Pr



CH2CH═CH2
CF3



CH2CH═CH2
SMe



CH2CH═CH2
Ph



CH2CH═CH2
Ph(2-Cl)



CH2CH═CH2
Ph(3-Cl)



CH2CH═CH2
Ph(4-Cl)



CH2CH═CH2
Ph(3-F)



CH2CH═CH2
Ph(3,5-di-F)



CH2CH═CH2
Ph(3-Me)



CH2C≡CH
Et



CH2C≡CH
n-Pr



CH2C≡CH
c-Pr



CH2C≡CH
CF3



CH2C≡CH
SMe



CH2C≡CH
Ph



CH2C≡CH
Ph(2-Cl)



CH2C≡CH
Ph(3-Cl)



CH2C≡CH
Ph(4-Cl)



CH2C≡CH
Ph(3-F)



CH2C≡CH
Ph(3,5-di-F)



CH2C≡CH
Ph(3-Me)



Ph
Et



Ph
n-Pr



Ph
c-Pr



Ph
CF3



Ph
SMe



Ph
Ph



Ph
Ph(2-Cl)



Ph
Ph(3-Cl)



Ph
Ph(4-Cl)



Ph
Ph(3-F)



Ph
Ph(3,5-di-F)



Ph
Ph(3-Me)



Ph(2-Me)
Et



Ph(2-Me)
n-Pr



Ph(2-Me)
c-Pr



Ph(2-Me)
CF3



Ph(2-Me)
SMe



Ph(2-Me)
Ph



Ph(2-Me)
Ph(2-Cl)



Ph(2-Me)
Ph(3-Cl)



Ph(2-Me)
Ph(4-Cl)



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



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



Ph(2-Me)
Ph(3-Me)



Ph(4-Me)
Et



Ph(4-Me)
n-Pr



Ph(4-Me)
c-Pr



Ph(4-Me)
CF3



Ph(4-Me)
SMe



Ph(4-Me)
Ph



Ph(4-Me)
Ph(2-Cl)



Ph(4-Me)
Ph(3-Cl)



Ph(4-Me)
Ph(4-Cl)



Ph(4-Me)
Ph(3-F)



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



Ph(4-Me)
Ph(3-Me)



Ph(2-Cl)
Et



Ph(2-Cl)
n-Pr



Ph(2-Cl)
c-Pr



Ph(2-Cl)
CF3



Ph(2-Cl)
SMe



Ph(2-Cl)
Ph



Ph(2-Cl)
Ph(2-Cl)



Ph(2-Cl)
Ph(3-Cl)



Ph(2-Cl)
Ph(4-Cl)



Ph(2-Cl)
Ph(3-F)



Ph(2-Cl)
Ph(3,5-di-F)



Ph(2-Cl)
Ph(3-Me)



Ph(3-Cl)
Et



Ph(3-Cl)
n-Pr



Ph(3-Cl)
c-Pr



Ph(3-Cl)
CF3



Ph(3-Cl)
SMe



Ph(3-Cl)
Ph



Ph(3-Cl)
Ph(2-Cl)



Ph(3-Cl)
Ph(3-Cl)



Ph(3-Cl)
Ph(4-Cl)



Ph(3-Cl)
Ph(3-F)



Ph(3-Cl)
Ph(3,5-di-F)



Ph(3-Cl)
Ph(3-Me)



n-Pr
Et



n-Pr
n-Pr



n-Pr
c-Pr



n-Pr
CF3



n-Pr
SMe



n-Pr
Ph



n-Pr
Ph(2-Cl)



n-Pr
Ph(3-Cl)



n-Pr
Ph(4-Cl)



n-Pr
Ph(3-F)



n-Pr
Ph(3,5-di-F)



n-Pr
Ph(3-Me)



n-Bu
Et



n-Bu
n-Pr



n-Bu
c-Pr



n-Bu
CF3



n-Bu
SMe



n-Bu
Ph



n-Bu
Ph(2-Cl)



n-Bu
Ph(3-Cl)



n-Bu
Ph(4-Cl)



n-Bu
Ph(3-F)



n-Bu
Ph(3,5-di-F)



n-Bu
Ph(3-Me)



n-pent
Et



n-pent
n-Pr



n-pent
c-Pr



n-pent
CF3



n-pent
SMe



n-pent
Ph



n-pent
Ph(2-Cl)



n-pent
Ph(3-Cl)



n-pent
Ph(4-Cl)



n-pent
Ph(3-F)



n-pent
Ph(3,5-di-F)



n-pent
Ph(3-Me)



n-Hex
Et



n-Hex
n-Pr



n-Hex
c-Pr



n-Hex
CF3



n-Hex
SMe



n-Hex
Ph



n-Hex
Ph(2-Cl)



n-Hex
Ph(3-Cl)



n-Hex
Ph(4-Cl)



n-Hex
Ph(3-F)



n-Hex
Ph(3,5-di-F)



n-Hex
Ph(3-Me)



thp-4-yl
Et



thp-4-yl
n-Pr



thp-4-yl
c-Pr



thp-4-yl
CF3



thp-4-yl
SMe



thp-4-yl
Ph



thp-4-yl
Ph(2-Cl)



thp-4-yl
Ph(3-Cl)



thp-4-yl
Ph(4-Cl)



thp-4-yl
Ph(3-F)



thp-4-yl
Ph(3,5-di-F)



thp-4-yl
Ph(3-Me)



thtp-4-yl
Et



thtp-4-yl
n-Pr



thtp-4-yl
c-Pr



thtp-4-yl
CF3



thtp-4-yl
SMe



thtp-4-yl
Ph



thtp-4-yl
Ph(2-Cl)



thtp-4-yl
Ph(3-Cl)



thtp-4-yl
Ph(4-Cl)



thtp-4-yl
Ph(3-F)



thtp-4-yl
Ph(3,5-di-F)



thtp-4-yl
Ph(3-Me)



c-Hex
Et



c-Hex
n-Pr



c-Hex
c-Pr



c-Hex
CF3



c-Hex
SMe



c-Hex
Ph



c-Hex
Ph(2-Cl)



c-Hex
Ph(3-Cl)



c-Hex
Ph(4-Cl)



c-Hex
Ph(3-F)



c-Hex
Ph(3,5-di-F)



c-Hex
Ph(3-Me)



CH2CH2OCH3
Et



CH2CH2OCH3
n-Pr



CH2CH2OCH3
c-Pr



CH2CH2OCH3
CF3



CH2CH2OCH3
SMe



CH2CH2OCH3
Ph



CH2CH2OCH3
Ph(2-Cl)



CH2CH2OCH3
Ph(3-Cl)



CH2CH2OCH3
Ph(4-Cl)



CH2CH2OCH3
Ph(3-F)



CH2CH2OCH3
Ph(3,5-di-F)



CH2CH2OCH3
Ph(3-Me)



CH2CH2OCH2CH3
Et



CH2CH2OCH2CH3
n-Pr



CH2CH2OCH2CH3
c-Pr



CH2CH2OCH2CH3
CF3



CH2CH2OCH2CH3
SMe



CH2CH2OCH2CH3
Ph



CH2CH2OCH2CH3
Ph(2-Cl)



CH2CH2OCH2CH3
Ph(3-Cl)



CH2CH2OCH2CH3
Ph(4-Cl)



CH2CH2OCH2CH3
Ph(3-F)



CH2CH2OCH2CH3
Ph(3,5-di-F)



CH2CH2OCH2CH3
Ph(3-Me)



CH2CH2CH2OCH3
Et



CH2CH2CH2OCH3
n-Pr



CH2CH2CH2OCH3
c-Pr



CH2CH2CH2OCH3
CF3



CH2CH2CH2OCH3
SMe



CH2CH2CH2OCH3
Ph



CH2CH2CH2OCH3
Ph(2-Cl)



CH2CH2CH2OCH3
Ph(3-Cl)



CH2CH2CH2OCH3
Ph(4-Cl)



CH2CH2CH2OCH3
Ph(3-F)



CH2CH2CH2OCH3
Ph(3,5-di-F)



CH2CH2CH2OCH3
Ph(3-Me)



CH2CH2CH2OEt
Et



CH2CH2CH2OEt
n-Pr



CH2CH2CH2OEt
c-Pr



CH2CH2CH2OEt
CF3



CH2CH2CH2OEt
SMe



CH2CH2CH2OEt
Ph



CH2CH2CH2OEt
Ph(2-Cl)



CH2CH2CH2OEt
Ph(3-Cl)



CH2CH2CH2OEt
Ph(4-Cl)



CH2CH2CH2OEt
Ph(3-F)



CH2CH2CH2OEt
Ph(3,5-di-F)



CH2CH2CH2OEt
Ph(3-Me)





R12 is c-Pr







The present disclosure also includes Tables 1J through 2J, each of which is constructed the same as Table 9 above except that the row heading in Table 9 (i.e. “R12 is c-Pr”) is replaced with the respective row headings shown below. For example, in Table 1J the row heading is “R12 is CH3”, and R1 and R2 are as defined in Table 9 above. Thus, the first entry in Table 1J specifically discloses a compound of Formula 1 wherein X is CH; Y is C(O); R1 is CH3; R2 is Et; A is A-7; R12 is CH3; and R13 is cyano. Table 2J is constructed similarly.













Table
Row Heading







1J
R12 is CH3


2J
R12 is CH2CH3
















TABLE 10







embedded image







R2







Et


Ph(2-Me)


n-Pr


Ph(3-Cl)


c-Pr


Ph(4-Cl)


CF3


Ph(2-Me)


SMe


Ph(3-Me)


Ph


Ph(4-Me)


Ph(3-F)


Ph(3,5-di-F)


Ph(3-Me)





R1 is phenyl







The present disclosure also includes Tables 1K through 10K, each of which is constructed the same as Table 9 above except that the row heading in Table 10 (i.e. “R1 is Ph”) is replaced with the respective row headings shown below. For example, in Table 1K the row heading is “R1 is n-Bu”, and R2 is as defined in Table 10 above. Thus, the first entry in Table 1K specifically discloses a compound of Formula 1 wherein X is CH; Y is C(O); R1 is n-Bu; R2 is Ph; A is A-7; R12 is hydroxy; and R13 is nitro. Table 2K through 10K are constructed similarly.













Table
Row Heading
















 1K
R1 is n-Bu


 2K
R1 is n-pent


 3K
R1 is n-Hex


 4K
R1 is thp-4-yl


 5K
R1 is thtp-4-yl


 6K
R1 is c-Hex


 7K
R1 is CH2CH2OCH3


 8K
R1 is CH2CH2OCH2CH3


 9K
R1 is CH2CH2CH2OCH3


10K
R1 is CH2CH2CH2OCH2CH3
















TABLE 11







embedded image







R24







Q is CH2


H


Ph


Et


Ph(3-Cl)


n-Pr


Ph(3-F)


OCH2CH2OCH3


Ph(3-OMe)


Ph(4-OMe)


Ph(3,5-di-F)


Q is —CH2CH2—


H


Ph


Et


Ph(3-Cl)


n-Pr


Ph(3-F)


OCH2CH2OCH3


Ph(3-OMe)


Ph(4-OMe)


Ph(3,5-di-F)


Q is O


H


Ph


Et


Ph(3-Cl)


n-Pr


Ph(3-F)


OCH2CH2OCH3


Ph(3-OMe)


Ph(4-OMe)


Ph(3,5-di-F)


Q is NCH3


H


Ph


Et


Ph(3-Cl)


n-Pr


Ph(3-F)


OCH2CH2OCH3


Ph(3-OMe)


Ph(4-OMe)


Ph(3,5-di-F)


Q is S


H


Ph


Et


Ph(3-Cl)


n-Pr


Ph(3-F)


OCH2CH2OCH3


Ph(3-OMe)


Ph(4-OMe)


Ph(3,5-di-F)


Q is S(O)


H


Ph


Et


Ph(3-Cl)


n-Pr


Ph(3-F)


OCH2CH2OCH3


Ph(3-OMe)


Ph(4-OMe)


Ph(3,5-di-F)


Q is S(O)2


H


Ph


Et


Ph(3-Cl)


n-Pr


Ph(3-F)


OCH2CH2OCH3


Ph(3-OMe)


Ph(4-OMe)


Ph(3,5-di-F)
















TABLE 12







Table 12 is constructed the same as Table 11,


except the structure is replaced with







embedded image


















TABLE 13







embedded image







R24







Q is O


H


Ph


Et


Ph(3-Cl)


n-Pr


Ph(3-F)


OCH2CH2OCH3


Ph(3-OMe)


Ph(4-OMe)


Ph(3,5-di-F)


Q is NCH3


H


Ph


Et


Ph(3-Cl)


n-Pr


Ph(3-F)


OCH2CH2OCH3


Ph(3-OMe)


Ph(4-OMe)


Ph(3,5-di-F)


Q is S


H


Ph


Et


Ph(3-Cl)


n-Pr


Ph(3-F)


OCH2CH2OCH3


Ph(3-OMe)


Ph(4-OMe)


Ph(3,5-di-F)


Q is S(O)


H


Ph


Et


Ph(3-Cl)


n-Pr


Ph(3-F)


OCH2CH2OCH3


Ph(3-OMe)


Ph(4-OMe)


Ph(3,5-di-F)


Q is S(O)2


H


Ph


Et


Ph(3-Cl)


n-Pr


Ph(3-F)


OCH2CH2OCH3


Ph(3-OMe)


Ph(4-OMe)


Ph(3,5-di-F)
















TABLE 14







Table 14 is constructed the same as Table 13,


except the structure is replaced with




embedded image


















TABLE 15







Table 15 is constructed the same as Table 13,


except the structure is replaced with




embedded image


















TABLE 16







Table 16 is constructed the same as Table 13,


except the structure is replaced with




embedded image


















TABLE 17







Table 17 is constructed the same as Table 13,


except the structure is replaced with




embedded image


















TABLE 18







Table 18 is constructed the same as Table 13,


except the structure is replaced with




embedded image


















TABLE 19







embedded image







R1







Me


Et


n-Pr


i-Pr


c-Pr


n-Bu


i-Bu


s-Bu


c-Bu


t-Bu


n-pent


c-Pent


n-Hex


c-Hex


Ph


CH2-c-Pr


CH2-c-Bu


CH2SPh


CH2SCH3


CH2CF3


CH2Ph


Ph(4-Me)


CH2CHC(CH3)2


CH2CH2C≡CH


CH2CH═CCl2


CH2CH═CF2


CH2CF═CF2


CH2CCl═CCl2


CH2C≡CCH3


CH2OCH2CH3


CH2CH2OCH3


CH2SO2CH3


CH2SCH2CH3


Ph(2,3-di-OMe)


CH2SO2-n-Pr


CH2CH2SO2Et


Ph(2,4-di-OMe)


Ph(2,5-di-OMe)


Ph(2,6-di-OMe)


Ph(3,5-di-OMe)


CH2Ph(2-OMe)


CH2Ph(3-OMe)


CH2Ph(4-OMe)


CH2CH2SMe


CH2SCH2Ph


CH2SO2Ph


CH2CH2SEt


Ph(2,4-di-Cl)


Ph(2,5-di-Cl)


Ph(2,6-di-Cl)


Ph(3,5-di-Cl)


Ph(2,3-di-Me)


Ph(2,4-di-Me)


Ph(2,5-di-Me)


Ph(2,6-di-Me)


Ph(3,5-di-Me)


CH2-c-Hex


Ph(2,3-di-F)


Ph(2,4-di-F)


Ph(2,5-di-F)


Ph(2,6-di-F)


CH2CH2CF3


CH2C≡CH


Ph(2,3-di-Cl)


Ph(3,5-di-F)


isoxazolin-2-yl


Ph(2-Cl)


Ph(3-Cl)


Ph(4-Cl)


Ph(2-Me)


Ph(3-Me)


CH2OCH3


CH2CH═CH2


Ph(2-OMe)


Ph(3-OMe)


Ph(4-OMe)


Ph(2-CN)


Ph(3-CN)


Ph(4-CN)


Ph(2-F)


Ph(3-F)


Ph(4-F)


CH2S-n-Pr


CH2-c-Pent


oxazolin-2-yl


2-pyridinyl


3-pyridinyl


4-pyridinyl


Ph(2-NO2)


Ph(3-NO2)


Ph(4-NO2)


Ph(2-CF3)


Ph(3-CF3)


Ph(4-CF3)


Ph(2-Br)


Ph(3-Br)


Ph(4-Br)


CH2Ph(2-Me)


CH2Ph(3-Me)


CH2Ph(4-Me)


CH2Ph(2-Cl)


CH2Ph(3-Cl)


CH2Ph(4-Cl)


thiazol-3-yl


thiazol-2-yl


thiazolin-2-yl


thiazol-2-yl


oxazol-2-yl


CH2CF2CF3


CH═CH2


CH2(thf-2-yl)


CH2(3-methylisoxazolin-5-yl)


isoxazolin-4-yl


CH2(3-methylisoxazol-5-yl)


5-methylisoxazol-3-yl


4-methyloxazol-2-yl


4-methylthiazol-2-yl


CH2CH2CH═CH2


CH2SO2CH2CH3


CH2CH2SO2Me


CH2OCH2OCH3


3-methylthiazol-2-yl


5-chloropyridin-2-yl


5-methylpyridin-2-yl


5-methoxypyridin-2-yl


6-methylpyridin-2-yl


6-methylpyridin-3-yl


3-methoxypyridin-4-yl


3-methylpyridin-4-yl


3-chloropyridin-4-yl


CH2OCH2CH2OCH3


CH2C(CH3)C(CH3)2


n-hept


c-hept


thp-4-yl


thtp-4-yl


Ph(2,3-di-OMe)


Ph(3,4-di-OMe)


Ph(3,4-di-Me)


Ph(3,4-di-F)


Ph(3,4,5-tri-OMe)


Ph(2-I)


Ph(3-I)


Ph(4-I)


Ph(2-Et)


Ph(3-Et)


Ph(4-Et)


CH2CH2OCH2CH3


CH(CH3)CH2OCH3


Ph(2-OCF3)


Ph(3-OCF3)


Ph(4-OCF3)


Ph(2-Me-3-F)


Ph(2-Me-4-F)


Ph(2-Me-5-F)


Ph(2-F-3-Me)


Ph(2-F-4-Me)


Ph(2-F-5-Me)


Ph(3-F-4-Me)


Ph(3-F-5-Me)


Ph(3-Me-4-F)


CH2CH2CH2OCH3


CH2CH2CH2OCH2CH3


CH2(thp-2-yl)


CH2(thp-4-yl)


CH2CH2CH═CH2


CH2C≡CH


CH2CH2SCH3


CH2CH2SOCH3


CH2CH2SO2CH3


CH2CH2CH2SCH3


CH2CH2CH2SOCH3


CH2CH2CH2SO2CH3





R2 is Ph







The present disclosure also includes Tables 1U through 57U, each of which is constructed the same as Table 19 above except that the row heading in Table 19 (i.e. “R2 is Ph”) is replaced with the respective row headings shown below. For example, in Table 1U the row heading is “R2 is Me”, and R1 is as defined in Table 19 above. Thus, the first entry in Table 1U specifically discloses a compound of Formula 1 wherein X is CH; Y is C(O); R1 is Me; R2 is Me; R3 is OH; A is A-1; B1 is C-1; B2 is C-3; B3 is C-1; and each R14, R15, R18 and R19 is H. Tables 2U through 57U are constructed similarly.













Table
Row Heading







 1U
R2 is Me


 2U
R2 is Et


 3U
R2 is n-Pr


 4U
R2 is c-Pr


 5U
R2 is SMe


 6U
R2 is SO2Me


 7U
R2 is CF3


 8U
R2 is Ph(2-Cl)


 9U
R2 is Ph(3-Cl)


10U
R2 is Ph(4-Cl)


11U
R2 is Ph(2-Me)


12U
R2 is Ph(3-Me)


13U
R2 is Ph(4-Me)


14U
R2 is Ph(2-OMe)


15U
R2 is Ph(3-OMe)


16U
R2 is Ph(4-OMe)


17U
R2 is Ph(2-F)


18U
R2 is Ph(3-F)


19U
R2 is Ph(4-F)


20U
R2 is OMe


21U
R2 is OEt


22U
R2 is CH2Ph


23U
R2 is 2-pyridinyl


24U
R2 is 3-pyridinyl


25U
R2 is 4-pyridinyl


26U
R2 is H


27U
R2 is Ph(3,5-di-F)


28U
R2 is Ph(3,4-di-F)


29U
R2 is Ph(3,4,5-tri-F)


30U
R2 is Ph(2,3-di-F)


31U
R2 is Ph(3-CF3)


32U
R2 is Ph(4-CF3)


33U
R2 is Ph(3,5-di-CF3)


34U
R2 is n-Bu


35U
R2 is CH2OCH3


36U
R2 is CH2CH2OCH3


37U
R2 is CH2CH2CF3


38U
R2 is CH2CF3


39U
R2 is n-pent


40U
R2 is c-pent


41U
R2 is c-Hex


42U
R2 is n-Hex


43U
R2 is thp-4-yl


44U
R2 is Ph(2-CN)


45U
R2 is Ph(3-CN)


46U
R2 is Ph(4-CN)


47U
R2 is Ph(2-C≡CH)


48U
R2 is Ph(3-C≡CH)


49U
R2 is Ph(4-C≡CH)


50U
R2 is Ph(3-Me, 2-F)


51U
R2 is Ph(3-Me-4-F)


52U
R2 is Ph(3-Me, 5-F)


53U
R2 is Ph(3-Me, 6-F)


54U
R2 is Ph(3-F, 2-Me)


55U
R2 is Ph(3-F-4-Me)


56U
R2 is Ph(3-F-5-Me)


57U
R2 is Ph(3-F, 6-Me)
















TABLE 20







Table 20 is constructed the same as Table 19 except the structure is


replaced with







embedded image


















TABLE 21







Table 21 is constructed the same as Table 19 except the structure is


replaced with







embedded image


















TABLE 22







Table 22 is constructed the same as Table 19 except the structure is


replaced with







embedded image


















TABLE 23







Table 23 is constructed the same as Table 19 except the structure is


replaced with







embedded image


















TABLE 24







Table 24 is constructed the same as Table 19 except the structure is


replaced with







embedded image


















TABLE 25







Table 25 is constructed the same as Table 19 except the structure is


replaced with







embedded image


















TABLE 26







Table 26 is the same as Table 19 except the structure is replaced with







embedded image


















TABLE 27







embedded image







R1







Me


Et


n-Pr


i-Pr


c-Pr


n-Bu


i-Bu


s-Bu


c-Bu


t-Bu


n-pent


c-Pent


n-Hex


c-Hex


Ph


CH2-c-Pr


CH2-c-Bu


CH2SPh


CH2SCH3


CH2CF3


CH2Ph


Ph(4-Me)


CH2CHC(CH3)2


CH2CH2C≡CH


CH2CH═CCl2


CH2CH═CF2


CH2CF═CF2


CH2CCl═CCl2


CH2C≡CCH3


CH2OCH2CH3


CH2CH2OCH3


CH2SO2CH3


CH2SCH2CH3


Ph(2,3-di-OMe)


CH2SO2-n-Pr


CH2CH2SO2Et


Ph(2,4-di-OMe)


Ph(2,5-di-OMe)


Ph(2,6-di-OMe)


Ph(3,5-di-OMe)


CH2Ph(2-OMe)


CH2Ph(3-OMe)


CH2Ph(4-OMe)


CH2CH2SMe


CH2SCH2Ph


CH2SO2Ph


CH2CH2SEt


Ph(2,4-di-Cl)


Ph(2,5-di-Cl)


Ph(2,6-di-Cl)


Ph(3,5-di-Cl)


Ph(2,3-di-Me)


Ph(2,4-di-Me)


Ph(2,5-di-Me)


Ph(2,6-di-Me)


Ph(3,5-di-Me)


CH2-c-Hex


Ph(2,3-di-F)


Ph(2,4-di-F)


Ph(2,5-di-F)


Ph(2,6-di-F)


CH2CH2CF3


CH2C≡CH


Ph(2,3-di-Cl)


Ph(3,5-di-F)


isoxazolin-2-yl


Ph(2-Cl)


Ph(3-Cl)


Ph(4-Cl)


Ph(2-Me)


Ph(3-Me)


CH2OCH3


CH2CH═CH2


Ph(2-OMe)


Ph(3-OMe)


Ph(4-OMe)


Ph(2-CN)


Ph(3-CN)


Ph(4-CN)


Ph(2-F)


Ph(3-F)


Ph(4-F)


CH2S-n-Pr


CH2-c-Pent


oxazolin-2-yl


2-pyridinyl


3-pyridinyl


4-pyridinyl


Ph(2-NO2)


Ph(3-NO2)


Ph(4-NO2)


Ph(2-CF3)


Ph(3-CF3)


Ph(4-CF3)


Ph(2-Br)


Ph(3-Br)


Ph(4-Br)


CH2Ph(2-Me)


CH2Ph(3-Me)


CH2Ph(4-Me)


CH2Ph(2-Cl)


CH2Ph(3-Cl)


CH2Ph(4-Cl)


thiazol-3-yl


thiazol-2-yl


thiazolin-2-yl


thiazol-2-yl


oxazol-2-yl


CH2CF2CF3


CH═CH2


CH2(thf-2-yl)


CH2(3-methylisoxazolin-5-yl)


isoxazolin-4-yl


CH2(3-methylisoxazol-5-yl)


5-methylisoxazol-3-yl


4-methyloxazol-2-yl


4-methylthiazol-2-yl


CH2CH2CH═CH2


CH2SO2CH2CH3


CH2CH2SO2Me


CH2OCH2OCH3


3-methylthiazol-2-yl


5-chloropyridin-2-yl


5-methylpyridin-2-yl


5-methoxypyridin-2-yl


6-methylpyridin-2-yl


6-methylpyridin-3-yl


3-methoxypyridin-4-yl


3-methylpyridin-4-yl


3-chloropyridin-4-yl


CH2OCH2CH2OCH3


CH2C(CH3)C(CH3)2


n-hept


c-hept


thp-4-yl


thtp-4-yl


Ph(2,3-di-OMe)


Ph(3,4-di-OMe)


Ph(3,4-di-Me)


Ph(3,4-di-F)


Ph(3,4,5-tri-OMe)


Ph(2-I)


Ph(3-I)


Ph(4-I)


Ph(2-Et)


Ph(3-Et)


Ph(4-Et)


CH2CH2OCH2CH3


CH(CH3)CH2OCH3


Ph(2-OCF3)


Ph(3-OCF3)


Ph(4-OCF3)


Ph(2-Me-3-F)


Ph(2-Me-4-F)


Ph(2-Me-5-F)


Ph(2-F-3-Me)


Ph(2-F-4-Me)


Ph(2-F-5-Me)


Ph(3-F-4-Me)


Ph(3-F-5-Me)


Ph(3-Me-4-F)


CH2CH2CH2OCH3


CH2CH2CH2OCH2CH3


CH2(thp-2-yl)


CH2(thp-4-yl)


CH2CH2CH═CH2


CH2C≡CH


CH2CH2SCH3


CH2CH2SOCH3


CH2CH2SO2CH3


CH2CH2CH2SCH3


CH2CH2CH2SOCH3


CH2CH2CH2SO2CH3





R2 is Ph






The present disclosure also includes Tables 1BB through 57BB, each of which is constructed the same as Table 27 above except that the row heading in Table 27 (i.e. “R2 is Ph”) is replaced with the respective row headings shown below. For example, in Table 1BB the row heading is “R2 is Me”, and R1 is as defined in Table 27 above. Thus, the first entry in Table 1BB specifically discloses a compound of Formula 1 wherein X is CH; Y is C(O); R1 is Me; R2 is Me; R3 is OH; A is A-1; B1 is C-1; B2 is C-3; B3 is C-1; and each R14, R15, R18 and R19 is H. Tables 2BB through 57BB are constructed similarly.
















Table
Row Heading









 1BB
R2 is Me



 2BB
R2 is Et



 3BB
R2 is n-Pr



 4BB
R2 is c-Pr



 5BB
R2 is SMe



 6BB
R2 is SO2Me



 7BB
R2 is CF3



 8BB
R2 is Ph(2-Cl)



 9BB
R2 is Ph(3-Cl)



10BB
R2 is Ph(4-Cl)



11BB
R2 is Ph(2-Me)



12BB
R2 is Ph(3-Me)



13BB
R2 is Ph(4-Me)



14BB
R2 is Ph(2-OMe)



15BB
R2 is Ph(3-OMe)



16BB
R2 is Ph(4-OMe)



17BB
R2 is Ph(2-F)



18BB
R2 is Ph(3-F)



19BB
R2 is Ph(4-F)



20BB
R2 is OMe



21BB
R2 is OEt



22BB
R2 is CH2Ph



23BB
R2 is 2-pyridinyl



24BB
R2 is 3-pyridinyl



25BB
R2 is 4-pyridinyl



26BB
H



27BB
Ph(3,5-di-F)



28BB
Ph(3,4-di-F)



29BB
Ph(3,4,5-tri-F)



30BB
Ph(2,3-di-F)



31BB
Ph(3-CF3)



32BB
Ph(4-CF3)



33BB
Ph(3,5-di-CF3)



34BB
n-Bu



35BB
CH2OCH3



36BB
CH2CH2OCH3



37BB
CH2CH2CF3



38BB
CH2CF3



39BB
n-pent



40BB
c-pent



41BB
c-Hex



42BB
n-Hex



43BB
thp-4-yl



44BB
Ph(2-CN)



45BB
Ph(3-CN)



46BB
Ph(4-CN)



47BB
Ph(2-C≡CH)



48BB
Ph(3-C≡CH)



49BB
Ph(4-C≡CH)



50BB
Ph(3-Me, 2-F)



51BB
Ph(3-Me-4-F)



52BB
Ph(3-Me, 5-F)



53BB
Ph(3-Me, 6-F)



54BB
Ph(3-F, 2-Me)



55BB
Ph(3-F-4-Me)



56BB
Ph(3-F-5-Me)



57BB
Ph(3-F, 6-Me)

















TABLE 28







Table 28 is constructed the same as Table 27 except the structure is


replaced with







embedded image


















TABLE 29







Table 29 is constructed the same as Table 27 except the structure is


replaced with







embedded image


















TABLE 30







Table 30 is constructed the same as Table 27 except the structure is


replaced with







embedded image


















TABLE 31







Table 31 is constructed the same as Table 27 except the structure is


replaced with







embedded image


















TABLE 32







Table 32 is constructed the same as Table 27 except the structure is


replaced with







embedded image


















TABLE 33







Table 32 is constructed the same as Table 27 except the structure is


replaced with







embedded image


















TABLE 34







embedded image




R1







Me


Et


n-Pr


i-Pr


c-Pr


n-Bu


i-Bu


s-Bu


c-Bu


t-Bu


n-pent


c-Pent


n-Hex


c-Hex


Ph


CH2-c-Pr


CH2-c-Bu


CH2SPh


CH2SCH3


CH2CF3


CH2Ph


CH2CHC(CH3)2


CH2CH2C≡CH


CH2CH═CCl2


CH2CH═CF2


CH2CF═CF2


CH2CCl═CCl2


CH2C≡CCH3


CH2OCH2CH3


CH2CH2OCH3


CH2SO2CH3


CH2SCH2CH3


Ph(2,3-di-OMe)


CH2SO2-n-Pr


CH2CH2SO2Et


Ph(2,4-di-OMe)


Ph(2,5-di-OMe)


Ph(2,6-di-OMe)


Ph(3,5-di-OMe)


CH2Ph(2-OMe)


CH2Ph(3-OMe)


CH2Ph(4-OMe)


CH2SO2Ph


CH2SCH2Ph


CH2CH2SEt


Ph(2,4-di-Cl)


Ph(2,5-di-Cl)


Ph(2,6-di-C1)


Ph(3,5-di-C1)


Ph(2,3-di-Me)


Ph(2,4-di-Me)


Ph(2,5-di-Me)


Ph(2,6-di-Me)


Ph(3,5-di-Me)


CH2-c-Hex


Ph(2,3-di-F)


Ph(2,4-di-F)


Ph(2,5-di-F)


Ph(2,6-di-F)


CH2CH2CF3


CH2C≡CH


Ph(2,3-di-Cl)


Ph(3-NO2)


Ph(2-Cl)


Ph(3-Cl)


Ph(4-Cl)


Ph(2-Me)


Ph(3-Me)


CH2OCH3


CH2CH═CH2


Ph(2-OMe)


Ph(3-OMe)


Ph(4-OMe)


Ph(2-CN)


Ph(3-CN)


Ph(4-CN)


Ph(2-F)


Ph(3-F)


Ph(4-F)


CH2S-n-Pr


CH2-c-Pent


CH2CF2CF3


CH═CH2


Ph(2-NO2)


Ph(4-NO2)


Ph(2-CF3)


Ph(3-CF3)


Ph(4-CF3)


Ph(2-Br)


Ph(3-Br)


Ph(4-Br)


CH2Ph(2-Me)


CH2Ph(3-Me)


CH2Ph(4-Me)


CH2Ph(2-Cl)


CH2Ph(3-Cl)


CH2Ph(4-Cl)


CH2CH2SO2Me


CH2OCH2OCH3


CH2OCH2CH2OCH3


CH2C(CH3)C(CH3)2


Ph(4-Me)


CH2CH2SMe


Ph(3,5-di-F)





R2 is Ph







The present disclosure also includes Tables 1K through 4K, each of which is constructed the same as Table 11 above except that the row heading in Table 11 (i.e. “R2 is Ph”) is replaced with the respective row headings shown below. For example, in Table 1K the row heading is “R2 is Ph”, and R1 is as defined in Table 11 above. Thus, the first entry in Table 1K specifically discloses a compound of Formula 1P wherein X is N, Y is C(O), R1 is Me; R2 is c-Pr; R3 is OH; A is A-1; B1 is C-1; B2 is C-3; B3 is C-1; and each R14, R15, R18 and R19 is H. Tables 2K through 4K are constructed similarly.
















Table
Row Heading









1K
R2 is c-Pr



2K
R2 is SMe



3K
R2 is SO2Me



4K
R2 is CF3

















TABLE 35







embedded image




R1







Me


Et


n-Pr


i-Pr


c-Pr


n-Bu


i-Bu


s-Bu


c-Bu


t-Bu


n-pent


c-Pent


n-Hex


c-Hex


Ph


CH2-c-Pr


CH2-c-Bu


CH2SPh


CH2SCH3


CH2CF3


CH2Ph


CH2CHC(CH3)2


CH2CH2C≡CH


CH2CH═CCl2


CH2CH═CF2


CH2CF═CF2


CH2CCl═CCl2


CH2C≡CCH3


CH2OCH2CH3


CH2CH2OCH3


CH2SO2CH3


CH2SCH2CH3


Ph(2,3-di-OMe)


CH2SO2-n-Pr


CH2CH2SO2Et


Ph(2,4-di-OMe)


Ph(2,5-di-OMe)


Ph(2,6-di-OMe)


Ph(3,5-di-OMe)


CH2Ph(2-OMe)


CH2Ph(3-OMe)


CH2Ph(4-OMe)


CH2SO2Ph


CH2SCH2Ph


CH2CH2SEt


Ph(2,4-di-Cl)


Ph(2,5-di-Cl)


Ph(2,6-di-C1)


Ph(3,5-di-C1)


Ph(2,3-di-Me)


Ph(2,4-di-Me)


Ph(2,5-di-Me)


Ph(2,6-di-Me)


Ph(3,5-di-Me)


CH2-c-Hex


Ph(2,3-di-F)


Ph(2,4-di-F)


Ph(2,5-di-F)


Ph(2,6-di-F)


CH2CH2CF3


CH2C≡CH


Ph(2,3-di-Cl)


Ph(3-NO2)


Ph(2-Cl)


Ph(3-Cl)


Ph(4-Cl)


Ph(2-Me)


Ph(3-Me)


CH2OCH3


CH2CH═CH2


Ph(2-OMe)


Ph(3-OMe)


Ph(4-OMe)


Ph(2-CN)


Ph(3-CN)


Ph(4-CN)


Ph(2-F)


Ph(3-F)


Ph(4-F)


CH2S-n-Pr


CH2-c-Pent


CH2CF2CF3


CH═CH2


Ph(2-NO2)


Ph(4-NO2)


Ph(2-CF3)


Ph(3-CF3)


Ph(4-CF3)


Ph(2-Br)


Ph(3-Br)


Ph(4-Br)


CH2Ph(2-Me)


CH2Ph(3-Me)


CH2Ph(4-Me)


CH2Ph(2-Cl)


CH2Ph(3-Cl)


CH2Ph(4-Cl)


CH2CH2SO2Me


CH2OCH2OCH3


CH2OCH2CH2OCH3


CH2C(CH3)C(CH3)2


Ph(4-Me)


CH2CH2SMe


Ph(3,5-di-F)





R2 is Ph







The present disclosure also includes Tables 1L through 11L, each of which is constructed the same as Table 12 above except that the row heading in Table 12 (i.e. “R2 is Ph”) is replaced with the respective row headings shown below. For example, in Table 1L the row heading is “R2 is Ph”, and R1 is as defined in Table 12 above. Thus, the first entry in Table 1L specifically discloses a compound of Formula 1P wherein X is CH; Y is S(O)2; R1 is Me and R2 is c-Pr; R3 is OH; A is A-1; B1 is C-1; B2 is C-3; B3 is C-1; and each R14, R15, R18 and R19 is H. Tables 2L through 11L are constructed similarly.
















Table
Row Heading









 1L
R2 is c-Pr



 2L
R2 is n-Pr



 3L
R2 is SMe



 4L
R2 is SO2Me



 5L
R2 is CF3



 6L
R2 Ph(2-Cl)



 7L
R2 Ph(3-Cl)



 8L
R2 is Ph(4-Cl)



 9L
R2 is Ph(2-Me)



10L
R2 is Ph(3-Me)



11L
R2 is Ph(4-Me)










A compound of this invention will generally be used 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 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 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. 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), 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 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 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 invention 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 invention 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-B. Without further elaboration, it is believed that one skilled in the art using the preceding description can utilize the present invention 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


















Compound 4
98.5%



silica aerogel
 0.5%



synthetic amorphous fine silica
 1.0%










EXAMPLE B

Wettable Powder


















Compound 2
65.0%



dodecylphenol polyethylene glycol ether
 2.0%



sodium ligninsulfonate
 4.0%



sodium silicoaluminate
 6.0%



montmorillonite (calcined)
23.0%










EXAMPLE C

Granule


















Compound 12
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 8
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 2
10.0%



polyoxyethylene sorbitol hexoleate
20.0%



C6-C10 fatty acid methyl ester
70.0%










EXAMPLE F

Microemulsion


















Compound 12
 5.0%



polyvinylpyrrolidone-vinyl acetate copolymer
30.0%



alkylpolyglycoside
30.0%



glyceryl monooleate
15.0%



Water
20.0%










These compounds generally show highest activity for early postemergence weed control (i.e. applied when the emerged weed seedlings are still young) 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 invention, 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 the preferred 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 invention may show tolerance to important agronomic crops including, but 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). Compounds of the invention are particularly useful for selective control of weeds in wheat, barley, and particularly maize, soybean, cotton and perennial plantation crops such as sugarcane and citrus. Compounds of this invention 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 the compounds of the invention have both postemergent and preemergent 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 the invention, 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 invention 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 a compound of this invention is about 0.001 to 20 kg/ha with a typical range of about 0.004 to 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 this invention 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 the compounds of the invention with other herbicides can broaden the spectrum of activity against additional weed species, and suppress the proliferation of any resistant biotypes. Thus the present invention 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 invention, 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 invention 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, clefoxydim, clethodim, clodinafop-propargyl, clomazone, clomeprop, clopyralid, clopyralid-olamine, cloransulam-methyl, cumyluron, cyanazine, cycloate, 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, 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, glyphosate and its salts such as ammonium, isopropylammonium, potassium, sodium (including sesquisodium) and trimesium (alternatively named sulfosate), halo sulfuron-methyl, haloxyfop-etotyl, haloxyfop-methyl, hexazinone, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr-ammonium, imazosulfuron, indanofan, iodosulfuron-methyl, ioxynil, ioxynil octanoate, ioxynil-sodium, 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, 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, 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, tiocarbazil, topramezone, tralkoxydim, tri-allate, triasulfuron, triaziflam, tribenuron-methyl, triclopyr, triclopyr-butotyl, triclopyr-triethylammonium, tridiphane, trietazine, trifloxysulfuron, trifluralin, triflusulfuron-methyl, tritosulfuron and vernolate. 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 invention 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 invention 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 the invention 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 the invention. 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 invention 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 invention can also be used in combination with herbicide safeners such as allidochlor, benoxacor, BCS (1-bromo-4-[(chloromethyl)sulfonyl]benzene), cloquintocet-mexyl, cyometrinil, cyprosulfonamide, dichlormid, 4-(dichloroacetyl)-1-oxa-4-azospiro[4.5]decane (MON 4660), 2-(dichloromethyl)-2-methyl-1,3-dioxolane (MG 191), dicyclonon, dietholate, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen-ethyl, mefenpyr-diethyl, mephenate, methoxyphenone ((4-methoxy-3-methylphenyl)(3-methylphenyl)methanone), naphthalic anhydride (1,8-naphthalic anhydride) and oxabetrinil to increase safety to certain crops. Antidotally effective amounts of the herbicide safeners can be applied at the same time as the compounds of this invention, or applied as seed treatments. Therefore an aspect of the present invention relates to a herbicidal mixture comprising a compound of this invention 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 invention 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 invention 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 the invention (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.


Preferred 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 are mixtures of a compound of this invention with a herbicide selected from the group consisting of 2,4-D, ametryne, aminocyclopyrachlor, aminopyralid, atrazine, bromacil, bromoxynil, bromoxynil octanoate, carfentrazone-ethyl, chlorimuron-ethyl, chlorsulfuron, clopyralid, clopyralid-olamine, dicamba and its diglycolammonium, dimethylammonium, potassium and sodium salts, diflufenican, dimethenamid, dimethenamid-P, diuron, florasulam, flufenacet, flumetsulam, flumioxazin, flupyrsulfuron-methyl, flupyrsulfuron-methyl-sodium, fluroxypyr, glyphosate (particularly glyphosate-isopropylammonium, glyphosate-sodium, glyphosate-potassium, glyphosate-trimesium), hexazinone, imazamethabenz-methyl, imazaquin, imazethapyr, iodosulfuron-methyl, lactofen, lenacil, linuron, MCPA and its dimethylammonium, potassium and sodium salts, MCPA-isoctyl, MCPA-thioethyl, mesosulfuron-methyl, S-metolachlor, metribuzin, metsulfuron-methyl, nicosulfuron, oxyfluorfen, pendimethalin, pinoxaden, pronamide, prosulfuron, pyroxasulfone, pyroxsulam, quinclorac, rimsulfuron, saflufenacil, sulfentrazone, thifensulfuron-methyl, triasulfuron, tribenuron-methyl, triclopyr, triclopyr-butotyl, and triclopyr-triethylammonium. Specifically preferred mixtures (compound numbers refer to compounds in Index Table A) are selected from the group: compound 2 and 2,4-D; compound 4 and 2,4-D; compound 8 and 2,4-D; compound 12 and 2,4-D; compound 2 and ametryne; compound 4 and ametryne; compound 8 and ametryne; compound 12 and ametryne; compound 2 and aminocyclopyrachlor; compound 4 and aminocyclopyrachlor; compound 8 and aminocyclopyrachlor; compound 12 and aminocyclopyrachlor; compound 2 and aminopyralid; compound 4 and aminopyralid; compound 8 and aminopyralid; compound 12 and aminopyralid; compound 2 and atrazine; compound 4 and atrazine; compound 8 and atrazine; compound 12 and atrazine; compound 2 and bromacil; compound 4 and bromacil; compound 8 and bromacil; compound 12 and bromacil; compound 2 and bromoxynil; compound 4 and bromoxynil; compound 8 and bromoxynil; compound 12 and bromoxynil; compound 2 and bromoxynil octanoate; compound 4 and bromoxynil octanoate; compound 8 and bromoxynil octanoate; compound 12 and bromoxynil octanoate; compound 2 and carfentrazone-ethyl; compound 4 and carfentrazone-ethyl; compound 8 and carfentrazone-ethyl; compound 12 and carfentrazone-ethyl; compound 2 and chlorimuron-ethyl; compound 4 and chlorimuron-ethyl; compound 8 and chlorimuron-ethyl; compound 12 and chlorimuron-ethyl; compound 2 and chlorsulfuron; compound 4 and chlorsulfuron; compound 8 and chlorsulfuron; compound 12 and chlorsulfuron; compound 2 and clopyralid; compound 4 and clopyralid; compound 8 and clopyralid; compound 12 and clopyralid; compound 2 and clopyralid-olamine; compound 4 and clopyralid-olamine; compound 8 and clopyralid-olamine; compound 12 and clopyralid-olamine; compound 2 and dicamba; compound 4 and dicamba; compound 8 and dicamba; compound 12 and dicamba; compound 2 and diflufenican; compound 4 and diflufenican; compound 8 and diflufenican; compound 12 and diflufenican; compound 2 and dimethenamid; compound 4 and dimethenamid; compound 8 and dimethenamid; compound 12 and dimethenamid; compound 2 and dimethenamid-P; compound 4 and dimethenamid-P; compound 8 and dimethenamid-P; compound 12 and dimethenamid-P; compound 2 and diuron; compound 4 and diuron; compound 8 and diuron; compound 12 and diuron; compound 2 and florasulam; compound 4 and florasulam; compound 8 and florasulam; compound 12 and florasulam; compound 2 and flufenacet; compound 4 and flufenacet; compound 8 and flufenacet; compound 12 and flufenacet; compound 2 and flumetsulam; compound 4 and flumetsulam; compound 8 and flumetsulam; compound 12 and flumetsulam; compound 2 and flumioxazin; compound 4 and flumioxazin; compound 8 and flumioxazin; compound 12 and flumioxazin; compound 2 and flupyrsulfuron-methyl; compound 4 and flupyrsulfuron-methyl; compound 8 and flupyrsulfuron-methyl; compound 12 and flupyrsulfuron-methyl; compound 2 and flupyrsulfuron-methyl-sodium; compound 4 and flupyrsulfuron-methyl-sodium; compound 8 and flupyrsulfuron-methyl-sodium; compound 12 and flupyrsulfuron-methyl-sodium; compound 2 and fluroxypyr; compound 4 and fluroxypyr; compound 8 and fluroxypyr; compound 12 and fluroxypyr; compound 2 and glyphosate; compound 4 and glyphosate; compound 8 and glyphosate; compound 12 and glyphosate; compound 2 and hexazinone; compound 4 and hexazinone; compound 8 and hexazinone; compound 12 and hexazinone; compound 2 and imazamethabenz-methyl; compound 4 and imazamethabenz-methyl; compound 8 and imazamethabenz-methyl; compound 12 and imazamethabenz-methyl; compound 2 and imazaquin; compound 4 and imazaquin; compound 8 and imazaquin; compound 12 and imazaquin; compound 2 and imazethapyr; compound 4 and imazethapyr; compound 8 and imazethapyr; compound 12 and imazethapyr; compound 2 and iodosulfuron-methyl; compound 4 and iodosulfuron-methyl; compound 8 and iodosulfuron-methyl; compound 12 and iodosulfuron-methyl; compound 2 and lactofen; compound 4 and lactofen; compound 8 and lactofen; compound 12 and lactofen; compound 2 and lenacil; compound 4 and lenacil; compound 8 and lenacil; compound 12 and lenacil; compound 2 and linuron; compound 4 and linuron; compound 8 and linuron; compound 12 and linuron; compound 2 and MCPA; compound 4 and MCPA; compound 8 and MCPA; compound 12 and MCPA; compound 2 and MCPA-isoctyl; compound 4 and MCPA-isoctyl; compound 8 and MCPA-isoctyl; compound 12 and MCPA-isoctyl; compound 2 and MCPA-thioethyl; compound 4 and MCPA-thioethyl; compound 8 and MCPA-thioethyl; compound 12 and MCPA-thioethyl; compound 2 and mesosulfuron-methyl; compound 4 and mesosulfuron-methyl; compound 8 and mesosulfuron-methyl; compound 12 and mesosulfuron-methyl; compound 2 and S-metolachlor; compound 4 and S-metolachlor; compound 8 and S-metolachlor; compound 12 and S-metolachlor; compound 2 and metribuzin; compound 4 and metribuzin; compound 8 and metribuzin; compound 12 and metribuzin; compound 2 and metsulfuron-methyl; compound 4 and metsulfuron-methyl; compound 8 and metsulfuron-methyl; compound 12 and metsulfuron-methyl; compound 2 and nicosulfuron; compound 4 and nicosulfuron; compound 8 and nicosulfuron; compound 12 and nicosulfuron; compound 2 and oxyfluorfen; compound 4 and oxyfluorfen; compound 8 and oxyfluorfen; compound 12 and oxyfluorfen; compound 2 and pendimethalin; compound 4 and pendimethalin; compound 8 and pendimethalin; compound 12 and pendimethalin; compound 2 and pinoxaden; compound 4 and pinoxaden; compound 8 and pinoxaden; compound 12 and pinoxaden; compound 2 and pronamide; compound 4 and pronamide; compound 8 and pronamide; compound 12 and pronamide; compound 2 and prosulfuron; compound 4 and prosulfuron; compound 8 and prosulfuron; compound 12 and prosulfuron; compound 2 and pyroxasulfone; compound 4 and pyroxasulfone; compound 8 and pyroxasulfone; compound 12 and pyroxasulfone; compound 2 and pyroxsulam; compound 4 and pyroxsulam; compound 8 and pyroxsulam; compound 12 and pyroxsulam; compound 2 and quinclorac; compound 4 and quinclorac; compound 8 and quinclorac; compound 12 and quinclorac; compound 2 and rimsulfuron; compound 4 and rimsulfuron; compound 8 and rimsulfuron; compound 12 and rimsulfuron; compound 2 and saflufenacil; compound 4 and saflufenacil; compound 8 and saflufenacil; compound 12 and saflufenacil; compound 2 and sulfentrazone; compound 4 and sulfentrazone; compound 8 and sulfentrazone; compound 12 and sulfentrazone; compound 2 and thifensulfuron-methyl; compound 4 and thifensulfuron-methyl; compound 8 and thifensulfuron-methyl; compound 12 and thifensulfuron-methyl; compound 2 and triasulfuron; compound 4 and triasulfuron; compound 8 and triasulfuron; compound 12 and triasulfuron; compound 2 and tribenuron-methyl; compound 4 and tribenuron-methyl; compound 8 and tribenuron-methyl; compound 12 and tribenuron-methyl; compound 2 and triclopyr; compound 4 and triclopyr; compound 8 and triclopyr; compound 12 and triclopyr; compound 2 and triclopyr-butotyl; compound 4 and triclopyr-butotyl; compound 8 and triclopyr-butotyl; compound 12 and triclopyr-butotyl; compound 2 and triclopyr-triethylammonium; compound 4 and triclopyr-triethylammonium; compound 8 and triclopyr-triethylammonium; compound 12 and triclopyr-triethylammonium.


Table A1 lists specific combinations of a compound of Formula 1 (i.e. Component (a)) with an additional active ingredient (i.e. Component (b)) illustrative of the mixtures, compositions and methods of the present invention. The first column of Table A1 lists compound 45 as the illustrative compound of Formula 1. 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 (b) compound is typically applied to a field-grown crop relative to Component (a). Thus, for example, the first line of Table A1 specifically discloses the combination of Component (a) with 2,4-D is typically applied in a weight ratio between 1:192 to 6:1. The remaining lines of Table A1 are to be construed similarly.













TABLE A1








More
Most




Typical
Typical
Typical




Weight
Weight
Weight


Component (a)
Component (b)
Ratio
Ratio
Ratio







Compound 47
2,4-D
1:192 to 6:1
1:64 to 2:1
1:24 to 1:3


Compound 47
acetochlor
1:768 to 2:1
1:256 to 1:2
1:96 to 1:11


Compound 47
acifluorfen
1:96 to 12:1
1:32 to 4:1
1:12 to 1:2


Compound 47
aclonifen
1:857 to 2:1
1:285 to 1:3
1:107 to






1:12


Compound 47
alachlor
1:768 to 2:1
1:256 to 1:2
1:96 to 1:11


Compound 47
ametryn
1:384 to 3:1
1:128 to 1:1
1:48 to 1:6


Compound 47
amicarbazone
1:192 to 6:1
1:64 to 2:1
1:24 to 1:3


Compound 47
amidosulfuron
1:6 to 168:1
1:2 to 56:1
1:1 to 11:1


Compound 47
amino-
1:48 to 24:1
1:16 to 8:1
1:6 to 2:1



cyclopyrachlor





Compound 47
aminopyralid
1:20 to 56:1
1:6 to 19:1
1:2 to 4:1


Compound 47
amitrole
1:768 to 2:1
1:256 to 1:2
1:96 to 1:11


Compound 47
anilofos
1:96 to 12:1
1:32 to 4:1
1:12 to 1:2


Compound 47
asulam
1:960 to 2:1
1:320 to 1:3
1:120 to






1:14


Compound 47
atrazine
1:192 to 6:1
1:64 to 2:1
1:24 to 1:3


Compound 47
azimsulfuron
1:6 to 168:1
1:2 to 56:1
1:1 to 11:1


Compound 47
beflubutamid
1:342 to 4:1
1:114 to 2:1
1:42 to 1:5


Compound 47
benfuresate
1:617 to 2:1
1:205 to 1:2
1:77 to 1:9


Compound 47
bensulfuron
1:25 to 45:1
1:8 to 15:1
1:3 to 3:1


Compound 47
bentazon
1:192 to 6:1
1:64 to 2:1
1:24 to 1:3


Compound 47
benzobicyclon
1:85 to 14:1
1:28 to 5:1
1:10 to 1:2


Compound 47
benzofenap
1:257 to 5:1
1:85 to 2:1
1:32 to 1:4


Compound 47
bicyclopyrone
1:42 to 27:1
1:14 to 9:1
1:5 to 2:1


Compound 47
bifenox
1:257 to 5:1
1:85 to 2:1
1:32 to 1:4


Compound 47
bispyribac-
1:10 to 112:1
1:3 to 38:1
1:1 to 7:1



sodium





Compound 47
bromacil
1:384 to 3:1
1:128 to 1:1
1:48 to 1:6


Compound 47
bromobutide
1:384 to 3:1
1:128 to 1:1
1:48 to 1:6


Compound 47
bromoxynil
1:96 to 12:1
1:32 to 4:1
1:12 to 1:2


Compound 47
butachlor
1:768 to 2:1
1:256 to 1:2
1:96 to 1:11


Compound 47
butafenacil
1:42 to 27:1
1:14 to 9:1
1:5 to 2:1


Compound 47
butylate
1:1542 to 1:2
1:514 to 1:5
1:192 to






1:22


Compound 47
carfenstrole
1:192 to 6:1
1:64 to 2:1
1:24 to 1:3


Compound 47
carfentrazone
1:128 to 9:1
1:42 to 3:1
1:16 to 1:2


Compound 47
chlorimuron
1:8 to 135:1
1:2 to 45:1
1:1 to 9:1


Compound 47
chlorotoluron
1:768 to 2:1
1:256 to 1:2
1:96 to 1:11


Compound 47
chlorsulfuron
1:6 to 168:1
1:2 to 56:1
1:1 to 11:1


Compound 47
cincosulfuron
1:17 to 68:1
1:5 to 23:1
1:2 to 5:1


Compound 47
cinidon-ethyl
1:384 to 3:1
1:128 to 1:1
1:48 to 1:6


Compound 47
cinmethylin
1:34 to 34:1
1:11 to 12:1
1:4 to 3:1


Compound 47
clethodim
1:48 to 24:1
1:16 to 8:1
1:6 to 2:1


Compound 47
clodinafop
1:20 to 56:1
1:6 to 19:1
1:2 to 4:1


Compound 47
clomazone
1:384 to 3:1
1:128 to 1:1
1:48 to 1:6


Compound 47
clomeprop
1:171 to 7:1
1:57 to 3:1
1:21 to 1:3


Compound 47
clopyralid
1:192 to 6:1
1:64 to 2:1
1:24 to 1:3


Compound 47
cloransulam
1:12 to 96:1
1:4 to 32:1
1:1 to 6:1


Compound 47
cumyluron
1:384 to 3:1
1:128 to 1:1
1:48 to 1:6


Compound 47
cyanazine
1:384 to 3:1
1:128 to 1:1
1:48 to 1:6


Compound 47
cyclosul-
1:17 to 68:1
1:5 to 23:1
1:2 to 5:1



famuron





Compound 47
cycloxydim
1:96 to 12:1
1:32 to 4:1
1:12 to 1:2


Compound 47
cyhalofop
1:25 to 45:1
1:8 to 15:1
1:3 to 3:1


Compound 47
daimuron
1:192 to 6:1
1:64 to 2:1
1:24 to 1:3


Compound 47
desmedipham
1:322 to 4:1
1:107 to 2:1
1:40 to 1:5


Compound 47
dicamba
1:192 to 6:1
1:64 to 2:1
1:24 to 1:3


Compound 47
dichlobenil
1:1371 to 1:2
1:457 to 1:4
1:171 to






1:20


Compound 47
dichlorprop
1:925 to 2:1
1:308 to 1:3
1:115 to






1:13


Compound 47
diclofop
1:384 to 3:1
1:128 to 1:1
1:48 to 1:6


Compound 47
diclosulam
1:10 to 112:1
1:3 to 38:1
1:1 to 7:1


Compound 47
difenzoquat
1:288 to 4:1
1:96 to 2:1
1:36 to 1:4


Compound 47
diflufenican
1:857 to 2:1
1:285 to 1:3
1:107 to






1:12


Compound 47
diflufenzopyr
1:12 to 96:1
1:4 to 32:1
1:1 to 6:1


Compound 47
dimethachlor
1:768 to 2:1
1:256 to 1:2
1:96 to 1:11


Compound 47
dimethametryn
1:192 to 6:1
1:64 to 2:1
1:24 to 1:3


Compound 47
dimethenamid
1:384 to 3:1
1:128 to 1:1
1:48 to 1:6


Compound 47
dithiopyr
1:192 to 6:1
1:64 to 2:1
1:24 to 1:3


Compound 47
diuron
1:384 to 3:1
1:128 to 1:1
1:48 to 1:6


Compound 47
EPTC
1:768 to 2:1
1:256 to 1:2
1:96 to 1:11


Compound 47
esprocarb
1:1371 to 1:2
1:457 to 1:4
1:171 to






1:20


Compound 47
ethalfluralin
1:384 to 3:1
1:128 to 1:1
1:48 to 1:6


Compound 47
ethametsulfuron
1:17 to 68:1
1:5 to 23:1
1:2 to 5:1


Compound 47
ethoxyfen
1:8 to 135:1
1:2 to 45:1
1:1 to 9:1


Compound 47
ethoxysulfuron
1:20 to 56:1
1:6 to 19:1
1:2 to 4:1


Compound 47
etobenzanid
1:257 to 5:1
1:85 to 2:1
1:32 to 1:4


Compound 47
fenoxaprop
1:120 to 10:1
1:40 to 4:1
1:15 to 1:2


Compound 47
fenoxasulfone
1:85 to 14:1
1:28 to 5:1
1:10 to 1:2


Compound 47
fentrazamide
1:17 to 68:1
1:5 to 23:1
1:2 to 5:1


Compound 47
flazasulfuron
1:17 to 68:1
1:5 to 23:1
1:2 to 5:1


Compound 47
florasulam
1:2 to 420:1
1:1 to 140:1
2:1 to 27:1


Compound 47
fluazifop
1:192 to 6:1
1:64 to 2:1
1:24 to 1:3


Compound 47
flucarbazone
1:8 to 135:1
1:2 to 45:1
1:1 to 9:1


Compound 47
flucetosulfuron
1:8 to 135:1
1:2 to 45:1
1:1 to 9:1


Compound 47
flufenacet
1:257 to 5:1
1:85 to 2:1
1:32 to 1:4


Compound 47
flumetsulam
1:24 to 48:1
1:8 to 16:1
1:3 to 3:1


Compound 47
flumiclorac
1:10 to 112:1
1:3 to 38:1
1:1 to 7:1


Compound 47
flumioxazin
1:25 to 45:1
1:8 to 15:1
1:3 to 3:1


Compound 47
fluometuron
1:384 to 3:1
1:128 to 1:1
1:48 to 1:6


Compound 47
flupyrsulfuron
1:3 to 336:1
1:1 to 112:1
2:1 to 21:1


Compound 47
fluridone
1:384 to 3:1
1:128 to 1:1
1:48 to 1:6


Compound 47
fluroxypyr
1:96 to 12:1
1:32 to 4:1
1:12 to 1:2


Compound 47
flurtamone
1:857 to 2:1
1:285 to 1:3
1:107 to






1:12


Compound 47
fomesafen
1:96 to 12:1
1:32 to 4:1
1:12 to 1:2


Compound 47
foramsulfuron
1:13 to 84:1
1:4 to 28:1
1:1 to 6:1


Compound 47
glufosinate
1:288 to 4:1
1:96 to 2:1
1:36 to 1:4


Compound 47
glyphosate
1:288 to 4:1
1:96 to 2:1
1:36 to 1:4


Compound 47
halosulfuron
1:17 to 68:1
1:5 to 23:1
1:2 to 5:1


Compound 47
haloxyfop
1:34 to 34:1
1:11 to 12:1
1:4 to 3:1


Compound 47
hexazinone
1:192 to 6:1
1:64 to 2:1
1:24 to 1:3


Compound 47
imazamox
1:13 to 84:1
1:4 to 28:1
1:1 to 6:1


Compound 47
imazapic
1:20 to 56:1
1:6 to 19:1
1:2 to 4:1


Compound 47
imazapyr
1:85 to 14:1
1:28 to 5:1
1:10 to 1:2


Compound 47
imazaquin
1:34 to 34:1
1:11 to 12:1
1:4 to 3:1


Compound 47
imazethabenz
1:171 to 7:1
1:57 to 3:1
1:21 to 1:3


Compound 47
imazethapyr
1:24 to 48:1
1:8 to 16:1
1:3 to 3:1


Compound 47
imazosulfuron
1:27 to 42:1
1:9 to 14:1
1:3 to 3:1


Compound 47
indanofan
1:342 to 4:1
1:114 to 2:1
1:42 to 1:5


Compound 47
indaziflam
1:25 to 45:1
1:8 to 15:1
1:3 to 3:1


Compound 47
iodosulfuron
1:3 to 336:1
1:1 to 112:1
2:1 to 21:1


Compound 47
ioxynil
1:192 to 6:1
1:64 to 2:1
1:24 to 1:3


Compound 47
ipfencarbazone
1:85 to 14:1
1:28 to 5:1
1:10 to 1:2


Compound 47
isoproturon
1:384 to 3:1
1:128 to 1:1
1:48 to 1:6


Compound 47
isoxaben
1:288 to 4:1
1:96 to 2:1
1:36 to 1:4


Compound 47
isoxaflutole
1:60 to 20:1
1:20 to 7:1
1:7 to 2:1


Compound 47
lactofen
1:42 to 27:1
1:14 to 9:1
1:5 to 2:1


Compound 47
lenacil
1:384 to 3:1
1:128 to 1:1
1:48 to 1:6


Compound 47
linuron
1:384 to 3:1
1:128 to 1:1
1:48 to 1:6


Compound 47
MCPA
1:192 to 6:1
1:64 to 2:1
1:24 to 1:3


Compound 47
MCPB
1:288 to 4:1
1:96 to 2:1
1:36 to 1:4


Compound 47
mecoprop
1:768 to 2:1
1:256 to 1:2
1:96 to 1:11


Compound 47
mefenacet
1:384 to 3:1
1:128 to 1:1
1:48 to 1:6


Compound 47
mefluidide
1:192 to 6:1
1:64 to 2:1
1:24 to 1:3


Compound 47
mesosulfuron
1:5 to 224:1
1:1 to 75:1
1:1 to 14:1


Compound 47
mesotrione
1:42 to 27:1
1:14 to 9:1
1:5 to 2:1


Compound 47
metamifop
1:42 to 27:1
1:14 to 9:1
1:5 to 2:1


Compound 47
metazachlor
1:384 to 3:1
1:128 to 1:1
1:48 to 1:6


Compound 47
metazosulfuron
1:25 to 45:1
1:8 to 15:1
1:3 to 3:1


Compound 47
metha-
1:768 to 2:1
1:256 to 1:2
1:96 to 1:11



benzthiazuron





Compound 47
metolachlor
1:768 to 2:1
1:256 to 1:2
1:96 to 1:11


Compound 47
metosulam
1:8 to 135:1
1:2 to 45:1
1:1 to 9:1


Compound 47
metribuzin
1:192 to 6:1
1:64 to 2:1
1:24 to 1:3


Compound 47
metsulfuron
1:2 to 560:1
1:1 to 187:1
3:1 to 35:1


Compound 47
molinate
1:1028 to 2:1
1:342 to 1:3
1:128 to






1:15


Compound 47
napropamide
1:384 to 3:1
1:128 to 1:1
1:48 to 1:6


Compound 47
naptalam
1:192 to 6:1
1:64 to 2:1
1:24 to 1:3


Compound 47
nicosulfuron
1:12 to 96:1
1:4 to 32:1
1:1 to 6:1


Compound 47
norflurazon
1:1152 to 1:1
1:384 to 1:3
1:144 to






1:16


Compound 47
orbencarb
1:1371 to 1:2
1:457 to 1:4
1:171 to






1:20


Compound 47
ortho-
1:20 to 56:1
1:6 to 19:1
1:2 to 4:1



sulfamuron





Compound 47
oryzalin
1:514 to 3:1
1:171 to 1:2
1:64 to 1:8


Compound 47
oxadiargyl
1:384 to 3:1
1:128 to 1:1
1:48 to 1:6


Compound 47
oxadiazon
1:548 to 3:1
1:182 to 1:2
1:68 to 1:8


Compound 47
oxasulfuron
1:27 to 42:1
1:9 to 14:1
1:3 to 3:1


Compound 47
oxaziclomefone
1:42 to 27:1
1:14 to 9:1
1:5 to 2:1


Compound 47
oxyfluorfen
1:384 to 3:1
1:128 to 1:1
1:48 to 1:6


Compound 47
paraquat
1:192 to 6:1
1:64 to 2:1
1:24 to 1:3


Compound 47
pendimethalin
1:384 to 3:1
1:128 to 1:1
1:48 to 1:6


Compound 47
penoxsulam
1:10 to 112:1
1:3 to 38:1
1:1 to 7:1


Compound 47
penthoxamid
1:384 to 3:1
1:128 to 1:1
1:48 to 1:6


Compound 47
pentoxazone
1:102 to 12:1
1:34 to 4:1
1:12 to 1:2


Compound 47
phenmedipham
1:102 to 12:1
1:34 to 4:1
1:12 to 1:2


Compound 47
picloram
1:96 to 12:1
1:32 to 4:1
1:12 to 1:2


Compound 47
picolinafen
1:34 to 34:1
1:11 to 12:1
1:4 to 3:1


Compound 47
pinoxaden
1:25 to 45:1
1:8 to 15:1
1:3 to 3:1


Compound 47
pretilachlor
1:192 to 6:1
1:64 to 2:1
1:24 to 1:3


Compound 47
primisulfuron
1:8 to 135:1
1:2 to 45:1
1:1 to 9:1


Compound 47
prodiamine
1:384 to 3:1
1:128 to 1:1
1:48 to 1:6


Compound 47
profoxydim
1:42 to 27:1
1:14 to 9:1
1:5 to 2:1


Compound 47
prometryn
1:384 to 3:1
1:128 to 1:1
1:48 to 1:6


Compound 47
propachlor
1:1152 to 1:1
1:384 to 1:3
1:144 to






1:16


Compound 47
propanil
1:384 to 3:1
1:128 to 1:1
1:48 to 1:6


Compound 47
propaquizafop
1:48 to 24:1
1:16 to 8:1
1:6 to 2:1


Compound 47
propoxy-
1:17 to 68:1
1:5 to 23:1
1:2 to 5:1



carbazone





Compound 47
propyrisulfuron
1:17 to 68:1
1:5 to 23:1
1:2 to 5:1


Compound 47
propyzamide
1:384 to 3:1
1:128 to 1:1
1:48 to 1:6


Compound 47
prosulfocarb
1:1200 to 1:2
1:400 to 1:4
1:150 to






1:17


Compound 47
prosulfuron
1:6 to 168:1
1:2 to 56:1
1:1 to 11:1


Compound 47
pyraclonil
1:42 to 27:1
1:14 to 9:1
1:5 to 2:1


Compound 47
pyraflufen
1:5 to 224:1
1:1 to 75:1
1:1 to 14:1


Compound 47
pyrasulfotole
1:13 to 84:1
1:4 to 28:1
1:1 to 6:1


Compound 47
pyrazolynate
1:857 to 2:1
1:285 to 1:3
1:107 to






1:12


Compound 47
pyrazosulfuron
1:10 to 112:1
1:3 to 38:1
1:1 to 7:1


Compound 47
pyrazoxyfen
1:5 to 224:1
1:1 to 75:1
1:1 to 14:1


Compound 47
pyribenzoxim
1:10 to 112:1
1:3 to 38:1
1:1 to 7:1


Compound 47
pyributicarb
1:384 to 3:1
1:128 to 1:1
1:48 to 1:6


Compound 47
pyridate
1:288 to 4:1
1:96 to 2:1
1:36 to 1:4


Compound 47
pyriftalid
1:10 to 112:1
1:3 to 38:1
1:1 to 7:1


Compound 47
pyriminobac
1:20 to 56:1
1:6 to 19:1
1:2 to 4:1


Compound 47
pyrimisulfan
1:17 to 68:1
1:5 to 23:1
1:2 to 5:1


Compound 47
pyrithiobac
1:24 to 48:1
1:8 to 16:1
1:3 to 3:1


Compound 47
pyroxasulfone
1:85 to 14:1
1:28 to 5:1
1:10 to 1:2


Compound 47
pyroxsulam
1:5 to 224:1
1:1 to 75:1
1:1 to 14:1


Compound 47
quinclorac
1:192 to 6:1
1:64 to 2:1
1:24 to 1:3


Compound 47
quizalofop
1:42 to 27:1
1:14 to 9:1
1:5 to 2:1


Compound 47
rimsulfuron
1:13 to 84:1
1:4 to 28:1
1:1 to 6:1


Compound 47
saflufenacil
1:25 to 45:1
1:8 to 15:1
1:3 to 3:1


Compound 47
sethoxydim
1:96 to 12:1
1:32 to 4:1
1:12 to 1:2


Compound 47
simazine
1:384 to 3:1
1:128 to 1:1
1:48 to 1:6


Compound 47
sulcotrione
1:120 to 10:1
1:40 to 4:1
1:15 to 1:2


Compound 47
sulfentrazone
1:147 to 8:1
1:49 to 3:1
1:18 to 1:3


Compound 47
sulfometuron
1:34 to 34:1
1:11 to 12:1
1:4 to 3:1


Compound 47
sulfosulfuron
1:8 to 135:1
1:2 to 45:1
1:1 to 9:1


Compound 47
tebuthiuron
1:384 to 3:1
1:128 to 1:1
1:48 to 1:6


Compound 47
tefuryltrione
1:42 to 27:1
1:14 to 9:1
1:5 to 2:1


Compound 47
tembotrione
1:31 to 37:1
1:10 to 13:1
1:3 to 3:1


Compound 47
tepraloxydim
1:25 to 45:1
1:8 to 15:1
1:3 to 3:1


Compound 47
terbacil
1:288 to 4:1
1:96 to 2:1
1:36 to 1:4


Compound 47
terbuthyl-
1:857 to 2:1
1:285 to 1:3
1:107 to



atrazine


1:12


Compound 47
terbutryn
1:192 to 6:1
1:64 to 2:1
1:24 to 1:3


Compound 47
thenylchlor
1:85 to 14:1
1:28 to 5:1
1:10 to 1:2


Compound 47
thiazopyr
1:384 to 3:1
1:128 to 1:1
1:48 to 1:6


Compound 47
thiencarbazone
1:3 to 336:1
1:1 to 112:1
2:1 to 21:1


Compound 47
thifensulfuron
1:5 to 224:1
1:1 to 75:1
1:1 to 14:1


Compound 47
thiobencarb
1:768 to 2:1
1:256 to 1:2
1:96 to 1:11


Compound 47
topramazone
1:6 to 168:1
1:2 to 56:1
1:1 to 11:1


Compound 47
tralkoxydim
1:68 to 17:1
1:22 to 6:1
1:8 to 2:1


Compound 47
triallate
1:768 to 2:1
1:256 to 1:2
1:96 to 1:11


Compound 47
triasulfuron
1:5 to 224:1
1:1 to 75:1
1:1 to 14:1


Compound 47
triaziflam
1:171 to 7:1
1:57 to 3:1
1:21 to 1:3


Compound 47
tribenuron
1:3 to 336:1
1:1 to 112:1
2:1 to 21:1


Compound 47
triclopyr
1:192 to 6:1
1:64 to 2:1
1:24 to 1:3


Compound 47
trifloxysulfuron
1:2 to 420:1
1:1 to 140:1
2:1 to 27:1


Compound 47
trifluralin
1:288 to 4:1
1:96 to 2:1
1:36 to 1:4


Compound 47
triflusulfuron
1:17 to 68:1
1:5 to 23:1
1:2 to 5:1


Compound 47
tritosulfuron
1:13 to 84:1
1:4 to 28:1
1:1 to 6:1









The present disclosure also includes Tables A2 through A22 which are each 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. Thus, for example, in Table A2 the entries below the “Component (a)” column heading all recite “Compound 50”, and the first line below the column headings in Table A2 specifically discloses a mixture of Compound 50 with 2,4-D. Tables A3 through A22 are constructed similarly.
















Table Number
Component (a) Column Entries









A2
Compound 50



A3
Compound 52



A4
Compound 59



A5
Compound 75



A6
Compound 81



A7
Compound 82



A8
Compound 83



A9
Compound 85



A10
Compound 87



A11
Compound 96



A12
Compound 97



A13
Compound 107



A14
Compound 118



A15
Compound 128



A16
Compound 133



A17
Compound 169



A18
Compound 175



A19
Compound 186



A20
Compound 218



A21
Compound 240



A22
Compound 243










The following Tests demonstrate the herbicidal effect of the compounds of this invention against specific weeds. The weed control afforded by the compounds is not limited, however, to the plant species tested. See Index Tables A-I for compound descriptions. The following abbreviations are used in the Index Tables which follow: “Cmpd” means Compound, Me is methyl, Et is ethyl, c-Pr is cyclopropyl, i-Bu is isobutyl (i.e. —CH2CH(CH3)2), Ph is phenyl, OMe is methoxy, c-hex is cyclohexyl, n-hex is normal hexyl Bn in benzyl, acetylene means —C≡CH, and SMe is methylthio. The abbreviation “Ex.” stands for “Example” and is followed by a number indicating in which example the compound is prepared. Substitution is noted in parentheses following the listed ring, for example Ph(4-OMe) indicates that the phenyl group is substituted by methoxy at the 4-position (relative to the point of attachment of the phenyl group to the remainder of the Formula 1 compound).









INDEX TABLE A









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Cmpd
R1
R2
R3
m.p.(° C.)





 1
CH3
c-Pr
OH
*


 2 (Ex. 1)
Ph
Ph
OH
* **


 3
Et
c-Pr
OH
*


 4
Ph(4-OMe)
Ph
OH
*


 7
Ph
Et
OH
*


 8
Ph(4-Me)
Ph
OH
*


 9
Ph(3-Cl)
Ph
OH
101-102


 10
Ph(2-Cl)
Ph
OH
142-143


 11
Ph(4-Cl)
Ph
OH
83-85


 12
Ph(2-Me)
Ph
OH
181-182


 13
Ph(4-Cl)
Ph
O−K+
105-108


 14
Ph
Ph
O−K+
128-130


 15
Ph(2-OMe)
Ph
OH
178-179


 17 (Ex. 2)
—CH2Ph
Ph
OH
57-58 **


 18
Ph(3-Me)
Ph
OH
77-78


 19
Ph(3-OMe)
Ph
OH
87-88


 22
Ph(3-F)
Ph
OH
72-74


 23
—CH2CH═CH2
Ph
OH
38-40


 24
Ph(4-F)
Ph
OH
131-132


 25
Ph
Ph(4-Cl)
OH
*


 26
Ph(2-F)
Ph
OH
142-144


 27
Ph(2,3-di-Me)
Ph
OH
155-157


 28
Ph(2,4-di-Me)
Ph
OH
186-187


 29
Ph(2,5-di-Me)
Ph
OH
169-171


 30
Ph
SMe
OH
92-94


 31
Ph(2,6-di-Me)
Ph
OH
177-178


 32
Ph(3,4-di-Me)
Ph
OH
165-166


 33
Ph(3,5-di-Me)
Ph
OH
156-157


 34
Ph
Ph(3-Cl)
OH
131-135


 35
Ph
Ph(2-Cl)
OH
138-142


 36
Ph(2-Me)
Ph(3-Cl)
OH
82-83


 37
Ph(2-Br)
Ph
OH
170-171


 38
Ph(3-Br)
Ph
OH
105-107


 39
Ph(4-Me)
Ph(3-Cl)
OH
78-80


 40
Ph(3-Cl-2-Me)
Ph
OH
170-171


 41
Ph(2-Cl-4-Me)
Ph
OH
183-184


 42
Ph
n-Bu
OH
145-147


 43
Ph(4-Cl-2-Me)
Ph
OH
172-173


 44
Ph(5-F-2-Me)
Ph
OH
169-170


 45
Ph(3-Me)
Ph(3-Cl)
OH
69-70


 46
Ph(2-Cl-6-Me)
Ph
OH
180-181


 47 (Ex. 5)
Ph(3-F-2-Me)
Ph
OH
168-169


 48
Ph(4-F-2-Me)
Ph
OH
153-155


 49
Et
Ph
OH
62-66


 50
n-Pr
Ph
OH
106-108


 51
Ph(2-F-5-Me)
Ph
OH
159-161


 52
Ph(5-Cl-2-Me)
Ph
OH
165-166


 53
Ph(4-F-3-Me)
Ph
OH
152-153


 54
Ph
n-hex
OH
138-140


 55
Me
Ph
OH
152-154


 56
Ph
3-thienyl
OH
*


 57
Ph(2,4-di-F)
Ph
OH
153-154


 58
Ph(2-F,3-Me)
Ph
OH
161-162


 59
—CH2(tetrahydrofuran-2yl)
Ph
OH
155-156


 60
Ph
i-Pr
OH
*


 61
—CH2C≡CH
Ph

151-153


 62
Ph(2-Me)
n-Bu
OH
100-101


 63
Ph(3-Me)
n-Bu
OH
136-137


 64
Ph(4-Cl)
Ph(3-Cl)
OH
140-142


 65
Ph
2-thienyl(5-Cl)
OH
*


 66
Ph
2-thienyl
OH
*


 67
Ph(4-Me)
n-Bu
OH
143-144


 68
Ph
i-Bu
OH
*


 69
Ph
Ph(3-Br)
OH
*


 70
Ph
Ph(4-Br)
OH
*


 71
Ph
Ph(2-Br)
OH
*


 72
n-Pr
n-Pr
OH
95-97


 73
Ph(2-Me)
n-Pr
OH
127-128


 74
—CH2(tetrahydrofuran-2-yl)
n-Pr
OH
95-96


 75
n-Bu
n-Pr
OH
88-89


 76
Ph
furan-2-yl
OH
*


 77
n-Pr
2-thienyl
OH
*


 78
Ph
n-pentyl
OH
*


 79
Ph(3-Me)
n-Pr
OH
140-142


 80
Ph
Ph(4-Me)
OH
164-169


 81
—CH2CH2CH2OCH3
Ph
OH
121-122


 82
Ph
Ph(2-Me)
OH
165-167


 83
Ph
Ph
OC(═O)-i-Bu
175-176


 84
—CH2(Ph(3,4-di-OMe))
n-Pr
OH
*


 85
—CH2CH2OCH3
Ph
OH
135-137


 86
n-Bu
Ph
OH
*


 87
Ph
c-Pr
OH
*


 88
Ph
Ph
OC(═O)-c-Pr
167-168


 89
n-pentyl
Ph
OH
100-102


 90
c-Pr
Ph
OH
172-174


 91
—CH2CH2OCH2CH2OCH3
Ph
OH
138-139


 92
Ph
c-pentyl
OH
*


 93
n-Pr
3-thienyl
OH
*


 94
n-hex
Ph
OH
95-97


 95
i-Pr
Ph
OH
163-165


 96
—CH2CH2OCH2CH3
Ph
OH
129-131


 97 (Ex. 10)
—CH2CH2OCH3
3-thienyl
OH
103-105


 98
—CH2(tetrahydrofuran-2-yl)
3-thienyl
OH
*


 99
c-hex
3-thienyl
OH
*


100
n-Pr
Ph(3-OMe)
OH
*


101
n-Pr
Ph(2-F)
OH
136-138


102
n-Pr
Ph(4-F)
OH
100-103


103
Bn
n-Pr
OH
*


104
—CH2(Ph(3-OMe))
n-Pr
OH
*


105
—CH2(Ph(3-OCF3))
n-Pr
OH
*


106
Ph
c-hex
OH
*


107
—CH(CH3)CH2OCH3
Ph
OH
122-123


108
—CH2CH2OCH3
2-thienyl
OH
*


109
—CH2(tetrahydrofuran-2-yl)
2-thienyl
OH
*


110
n-Pr
furan-2-yl
OH
*


111
—CH2CH2OCH3
furan-2-yl
OH
*


112
n-Pr
Ph(4-OMe)
OH
*


113 (Ex. 7)
Ph
3-pyridinyl
OH
**


114
Ph
c-Bu
OH
*


115
Et
Ph(3-Me)
OH
*


116
n-Bu
Ph(3-Me)
OH
*


117
—CH2CH2OCH3
Ph(3-Me)
OH
*


118
—CH2CH2CH2OCH3
Ph(3-Me)
OH
*


119
—CH2CH2OCH3
Ph(3,5-di-F)
OH
154-178


120
—CH2CH2CH2OCH3
Ph(3,5-di-F)
OH
139-140


121
n-Bu
Ph(3,5-di-F)
OH
144-145


122
Et
Ph(3,5-di-F)
OH
162-165


123
—CH2CH2OCH3
Ph(3-F)
OH
*


124
Et
Ph(3-F)
OH
*


125
n-Bu
Ph(3-F)
OH
*


126
—CH2CH2CH2OCH3
Ph(3-F)
OH
*


127
n-Pr
Ph(3-F)
OH
*


128 (Ex. 11)
c-hex
Ph
OH
160-163






**


129
tetrahydropyran-4-yl
Ph
OH
*


130
c-heptyl
Ph
OH
*


131
c-pentyl
Ph
OH
*


132
Ph(4-F-3-Me)
Ph(3-Br)
OH
*


133
Ph(4-F-3-Me)
Ph(3-Cl)
OH
*


134
n-Pr
Ph(4-Br)
OH
*


135
n-Pr
1-Me-pyrazol-3-yl
OH
*


136
—CH2CH2OCH3
1-Me-pyrazol-3-yl
OH
*


137
Et
Ph(3-Br)
OH
141-145


138
n-Bu
Ph(3-Br)
OH
112-113


139
—CH2CH2OCH3
Ph(3-Br)
OH
115-116


140
—CH2CH2CH2OCH3
Ph(3-Br)
OH
118-119


141
n-Pr
Ph(3-Br)
OH
134-137


142
—CH2(tetrahydrofuran-2-yl)
Ph(3-Cl)
OH
*


143
—CH2CH2CH2OCH3
Ph(3-Cl)
OH
*


144
Ph(5-Cl-2-Me)
Ph(3-Br)
OH
*


145
Et
Ph(3-Cl)
OH
114-115


146
n-Bu
Ph(3-Cl)
OH
104-112


147
—CH2CH2OCH3
Ph(3-Cl)
OH
124-125


148
Ph(5-Cl-2-Me)
Ph(3-Cl)
OH
*


149
n-Pr
1,4-benzodioxan-6-yl
OH
*


150
n-Pr
naphthalen-2-yl
OH
*


151
Ph(4-OMe)
Ph(3-Cl)
OH
154-156


152
n-Pr
Ph(3,5-di-F)
OH
*


153
n-Pr
c-Pr
OH
163-165


154
Ph(5-F-2-Me)
Ph(3-Br)
OH
*


155
n-Pr
Ph(3-CF3)
OH
129-131


156
n-Pr
Ph(3,5-di-Me)
OH
161-163


157
Ph(5-F-2-Me)
Ph(3-Cl)
OH
*


158
Ph(4-Et)
Ph(3,5-di-F)
OH
181-182


159
Ph(2-Me)
Ph(3,5-di-F)
OH
166-168


160
c-hex
c-Pr
OH
173-175


161
Ph
Ph(3,5-di-F)
OH
147-148


162
Ph(4-Me)
Ph(3,5-di-F)
OH
191-192


163
—CH2-c-hex
Ph(3,5-di-F)
OH
*


164
tetrahydrothiopyran-4-yl
Ph
OH
*


165
c-dodecahexyl
Ph
OH
*


166
Ph(4-F-2-Me)
Ph(3-Br)
OH
*


167
Ph(4-F-2-Me)
Ph(3-Cl)
OH
*


168 (Ex. 8)
(cis/trans)-tetrahydro-1-oxido-2H-
Ph
OH
**



thiopyran-4-yl





169 (Ex. 8)
(trans/cis)-tetrahydro-1-oxido-2H-
Ph
OH
**



thiopyran-4-yl





170
—CH2C≡CH
Ph(3,5-di-F)
OH
*


171
—CH2CH2OCH2CH2OCH3
Ph(3,5-di-F)
OH
*


172
n-Pr
Ph(3-Me)
OH
116-117


173
n-Pr
Ph(3,5-di-Cl)
OH
 97-100


174
Ph(4-Et)
Ph(3-Cl)
OH
146-148


175
Ph(4-Et)
Ph(3-Br)
OH
126-129


176
Ph(4-OMe)
Ph(3-Br)
OH
120-124


177
Ph(4-Et)
Ph(3-Br)
OH
139-142


178
Ph(5-F-2-Me)
Ph(3-Me)
OH
*


179
Ph(5-Cl-2-Me)
Ph(3,5-di-F)
OH
*


180
—CH2(tetrahydrofuran-2-yl)
Ph(3,5-di-F)
OH
*


181
c-hex
Ph(3,5-di-F)
OH
*


182
—CH2CH2OCH2CH3
Ph(3,5-di-F)
OH
*


183
Ph(5-F-2-Me)
Ph(3,5-di-F)
OH
*


184
Ph(5-Cl-2-Me)
Ph(3-F)
OH
*


185
c-hex
Ph(3-Me)
OH
*


186
tetrahydropyran-4-yl
3-thienyl
OH
*


187
c-hex
Ph(3-F)
OH
*


188
c-hex
furan-2-yl
OH
*


189
c-hex
2-thienyl
OH
*


190
n-Pr
Ph(3-Cl)
OH
123-125


191
Ph(4-F-3-Me)
Ph(3-F)
OH
*


192
Ph(4-F-2-Me)
Ph(3-Me)
OH
*


193
n-Bu
c-Pr
OH
140-142


194
c-hex
Ph(3-Et)
OH
*


195
c-hex
Ph(3-CF3)
OH
*


196
c-hex
Ph(3-OMe)
OH
*


197
c-hex
Ph(4-F)
OH
*


198
c-hex
Ph(3,4-di-F)
OH
*


199
Ph
Ph(3-F)
OH
*


200
Et
Bn
OH
*


201
Ph(2-Me)
Ph(3-F)
OH
*


202
Ph(4-Me)
Ph(3-F)
OH
*


203
Ph(4-OMe)
Ph(3-F)
OH
*


204
Ph(4-Et)
Ph(3-F)
OH
*


205
c-hex
Ph(3,4,5-tri-F)
OH
*


206
c-hex
Ph(3-Br)
OH
*


207
—CH2CH2CF3
Ph
OH
*


208
—CH2CH2CF3
Ph(3-F)
OH
69-70


209
Ph(2-Me)
Ph(3-Br)
OH
144-146


210
Ph(2-Me)
Ph(3-Me)
OH
152-154


211
Ph(4-Me)
Ph(3-Me)
OH
146-148


212
Ph(4-OMe)
Ph(3-Me)
OH
156-158


213
Ph(4-Et)
Ph(3-Me)
OH
147-148


214
—CH2CH2CHCH2
Ph
OH
124-127


215
c-octyl
Ph
OH
*


216
c-hex
Ph(4-acetylene)
OH
*


217
Ph
n-Pr
OH
145-147


218
Ph(3,4-di-OMe)
Ph
OH
164-165


219
Ph(4-Et)
Ph
OH
160-162


220
Ph(3-Et)
Ph
OH
126-127


255
Ph(2-Et)
Ph
OH
171-172


256
Ph(2,4-diOMe)
Ph
OH
182-183










257
—CH2CH2CH2CH2CH2—
OH
*





* See Index Table J for M.S. or 1H NMR data.


** See synthesis examples for 1H NMR data.













INDEX TABLE B









embedded image
















Cmpd
R1
R2
R3
m.p. (° C.)





 16
Ph
Ph
OS(O)2Ph(4-Me)
63-65


 20 (Ex. 3)
—CH2Ph
Ph
OH
56-57 **


 21 (Ex. 4)
—CH2Ph
Ph
OS(O)2Ph(4-Me)
52-53 **


221
n-Pr
2-thienyl
OH
*





* See Index Table J for M.S. or 1H NMR data.


** See synthesis example for 1H NMR data.













INDEX TABLE C









embedded image

















Cmpd
R1
R2
m.p. (° C.)







222
Ph(2,5-di-Me)
Ph
*



223 (Ex. 6)
Ph
Ph
**







* See Index Table J for M.S. or 1H NMR data.



** See synthesis examples for 1H NMR data.













INDEX TABLE D









embedded image
















Cmpd
R1
R2
R3
m.p. (° C.)





224
n-Pr
Ph(3,5-di-F)
OH
*


225
Ph
Ph
OH
125-127





* See Index Table J for M.S. or 1H NMR data.













INDEX TABLE E









embedded image
















Cmpd
R1
R2
R3
m.p.(° C.)





226
n-Pr
Ph
OH
*


227
n-Pr
3-thienyl
OH
*


228
—CH2CH2OCH3
3-thienyl
OH
*


229
—CH2(tetrahydrofuran-
3-thienyl
OH
*



2-yl)





230
n-Pr
furan-2-yl
OH
*


231
Et
Ph(3-Me)
OH
*


232
n-Bu
Ph(3-Me)
OH
*


233
—CH2CH2OCH3
Ph(3-Me)
OH
*


234
Ph(3-F-2-Me)
Ph
OH
*


235
—CH2CH2OCH3
Ph(3-F)
OH
*


236
Et
Ph(3-F)
OH
*


237
n-Bu
Ph(3-F)
OH
*


238
—CH2CH2CH2OCH3
Ph(3-F)
OH
*


239
Et
Ph
OH
*


240
n-Bu
Ph
OH
*


241
n-Pr
1,4-benzodioxan-6-yl
OH
*


242
n-Pr
naphthalen-2-yl
OH
*


243 (Ex. 9)
—CH2CH2OCH3
Ph(3,5-di-F)
OH
**


244
—CH2CH2CH2OCH3
Ph(3,5-di-F)
OH
*


245
n-Bu
Ph(3,5-di-F)
OH
*


246
Ph
Ph(3,5-di-F)
OH
158-159


247
c-dodecahexyl
Ph
OH
*


248
c-hex
Ph
OH
*


249
tetrahydropyran-4-yl
Ph
OH
*


250
—CH2(tetrahydrofuran-
Ph
OH
*



2-yl)





251
c-hex
Ph(3,4,5-tri-F)
OH
*


252
c-hex
Ph(3-Br)
OH
*


253
c-heptyl
Ph
OH
*


254
c-hex
Ph(4-acetylene)
OH
*





* See index table J for 1H NMR.


** See synthesis example for 1H NMR data.













INDEX TABLE F









embedded image















Cmpd
R1
R2
m.p. (° C.)





 2Q (Ex. 1)
Ph
Ph
**


 17Q (Ex. 2)
—CH2Ph
Ph
**


 23Q
—CH2CH═CH2
Ph
*


 47Q (Ex. 5)
Ph(3-F-2-Me)
Ph
**


 59Q
—CH2(tetrahydrofuran-2yl)
Ph
*


 61Q
—CH2C≡CH
Ph
*


 76Q
Ph
2-furanyl
*


 84Q
—CH2(Ph(3,4-di-OMe))
n-Pr
*


105Q
—CH2(Ph(3-OCF3))
n-Pr
*


113Q (Ex. 7)
Ph
3-pyridinyl
**


153Q
n-Pr
c-Pr
*


163Q
—CH2-c-hex
Ph(3,5-di-F)
*


212Q
Ph(4-OMe)
Ph(3-Me)
*









257Q
—CH2CH2CH2CH2CH2—
*





* See Index Table J for MS or 1H NMR data.


** See synthesis examples for 1H NMR data.













INDEX TABLE G









embedded image

















Cmpd
R1
R2
m.p. (° C.)







20Q (Ex. 3)
—CH2Ph
Ph
**







** See synthesis example for 1H NMR data.













INDEX TABLE H









embedded image


















m.p.


Cmpd
R1
R2
(° C.)





 2R (Ex. 1)
Ph
Ph
**


 17R (Ex. 2)
—CH2Ph
Ph
**


 23R
—CH2CH═CH2
Ph
*


 47R (Ex. 5)
Ph(3-F-2-Me)
Ph
**


 59R
—CH2(tetrahydrofuran-2-yl)
Ph
*


 61R
—CH2C≡CH
Ph
*


 76R
Ph
2-furanyl
*


 84R
—CH2(Ph(3,4-di-OMe))
n-Pr
*


105R
—CH2(Ph(3-OCF3))
n-Pr
*


 97R (Ex. 10)
—CH2CH2OCH3
3-thienyl
**


118R
—CH2CH2CH2OCH3
Ph(3-Me)
*


113R (Ex. 7)
Ph
3-pyridinyl
**


135R
n-Pr
1-Me-pyrazol-3-yl
*


128R (Ex. 11)
c-hex
Ph
**


153R
n-Pr
c-Pr
*


163R
—CH2-c-hex
Ph(3,5-di-F)
*


164R
tetrahydrothiopyran-4-yl
Ph
*


186R
tetrahydropyran-4-yl
3-thienyl
*


212R
Ph(4-OMe)
Ph(3-Me)
*


216R
c-hex
Ph(4-acetylene)
*


242R
n-Pr
naphthalene-2-yl
*


247R
c-dodecahexyl
Ph
*


243R (Ex. 9)
—CH2CH2OCH3
Ph(3,5-di-F)
**









257R
—CH2CH2CH2CH2CH2—
*





* See Index Table J for MS or 1H NMR data.


** See synthesis examples for 1H NMR data.













INDEX TABLE I









embedded image




















m.p.


Cmpd
R1
R2
R23
(° C.)





 2S (Ex. 1)
Ph
Ph
Et
**


 17S (Ex. 2)
—CH2Ph
Ph
Et
**


 23S
—CH2CH═CH2
Ph
Et
*


 59S
—CH2(tetrahydrofuran-
Ph
Et
*



2-yl)





 61S
—CH2C≡CH
Ph
Et
*


 84S
—CH2(Ph(3,4-di-OMe))
n-Pr
Et
*


105S
—CH2(Ph(3-OCF3))
n-Pr
Et
*


 97S (Ex. 10)
—CH2CH2OCH3
3-thienyl
Et
**


118S
—CH2CH2CH2OCH3
Ph(3-Me)
Et
*


113S (Ex. 7)
Ph
3-pyridinyl
Et
**


135S
n-Pr
1-Me-pyrazol-
Et
*




3-yl




128S (Ex. 11)
c-hex
Ph
Et
**


153S
n-Pr
c-Pr
Me
*


163S
—CH2-c-hex
Ph(3,5-di-F)
Et
*


164S
tetrahydrothiopyran-4-yl
Ph
Et
*


186S
tetrahydropyran-4-yl
3-thienyl
Et
*


212S
Ph(4-OMe)
Ph(3-Me)
Et
*


216S
c-hex
Ph(4-acetylene)
Et
*


242S
n-Pr
naphthalene-2-yl
Et
*


247S
c-dodecahexyl
Ph
Et
*


243S (Ex. 9)
—CH2CH2OCH3
Ph(3,5-di-F)
Et
**










257S
—CH2CH2CH2CH2CH2—
Et
*





* See Index Table J for MS or 1H NMR data.


** See synthesis examples for 1H NMR data.
















INDEX TABLE J








Cmpd
Mass spectra dataa or 1H NMR datab





  1
289


  3
303


  4
417


  7
339


  8
401


 25
421


 56
393


 60
353 (ESI, M + 1)


 65
427


 66
393


 68
367 (ESI, M + 1)



(500 MHz) δ 16.38 (s, 1H), 8.14 (s, 1H), 7.45 (t, 1H), 7.34 (dd, 1H), 7.32-7.23 (m, 3H), 7.10-7.05 (m,


 69
3H), 7.01-6.95 (m, 1H), 2.64 (t, 2H), 2.40 (t, 2H), 1.96 (dd, 2H).


 70
465


 71
463 (AP, M − H)


 76
377


 77
359


 78
381 (ESI, M + H)


 84
425 (AP, M − H)


 86
367


 87
351 (ESI, M + H)


 92
379 (ESI, M + H)


 93
359


 98
401


 99
399


100
381 (EST, M − H)


103
δ 16.41 (s, 1H), 8.09 (s, 1H), 7.42 (m, 3H), 7.21 (m, 2H), 5.29 (s, 2H), 2.79 (m, 2H), 2.77 (m, 2H),



2.65 (m, 2H), 2.15 (m, 2H), 1.75 (m, 2H), 0.94 (t, 3H).


104
δ 16.22 (s, 1H), 8.07 (s, 1H), 7.25 (m, 1H), 6.77 (m, 3H), 5.29 (s, 2H), 3.81 (s, 3H), 2.79 (m, 2H), 2.64



(m, 2H), 2.55 (m, 2H), 2.15 (m, 2H), 1.65 (m, 2H), 0.95 (t, 3H).


105
δ 16.41 (s, 1H), 8.06 (s, 1H), 7.41 (m, 1H), 7.14 (m, 3H), 5.32 (s, 2H), 2.81 (m, 2H), 2.62 (m, 2H),



2.52 (m, 2H), 2.15 (m, 2H), 1.81 (m, 2H), 0.95 (t, 3H).


106
393 (ESI, M + H)


108
375


109
401


110
343


111
359


112
382


114
365 (ESI, M + H)


115
353


116
381


117
383


118
397


123
387


124
357


125
385


126
401


127
δ 8.09 (s, 1H), 7.55-7.46 (m, 1H), 7.33-7.20 (m, 3H), 3.94-3.83 (m, 2H), 2.74 (t, 2H), 2.51 (t, 2H),



2.08 (quin, 2H), 1.63 (sxt, 2H), 0.78 (t, 3H).


129
395


130
407


131
379


132
495 (AP, M − H)


133
453


134
431 (ESI, M + H)


135
357


136
373


142
429


143
417


144
(500 MHz) δ 16.32 (br s, 1H), 8.22 (s, 1H), 7.55 (s, 1H), 7.46 (d, 1H), 7.25-7.06 (m, 5H), 2.70 (br s,



2H), 2.46 (d, 2H), 2.14 (s, 3H), 2.08-2.00 (m, 2H)


148
469


149
411


150
403


152
389


154
497


157
453


163
443


164
411


165
477


166
495 (AP, M − H)


167
453


170
385


171
449


178
433


179
471


180
431


181
429


182
419


183
455


184
453


185
δ 16.65 (br s, 1H), 8.00 (s, 1H), 7.20-7.40 (m, 4H), 3.90-4.00 (m, 1H), 0.90-2.80 (m, 19H).


186
401


187
411


188
383


189
399


191
437


192
433


194
421


195
461


196
423


197
411


198
429


199
403 (AP, M − H)


200
353


201
417 (AP, M − H)


202
417 (AP, M − H)


203
433 (AP, M − H)


204
431 (AP, M − H)


205
447


206
471


207
405 (AP, M − H)


215
421


216
417


221
359


222
412


224
417


226
379


227
385


228
401


229
427


230
369


231
379


232
407


233
409


234
445


235
413


236
383


237
411


238
427


239
365


240
393


241
437


242
429


244
445


245
429


247
503


248
419


249
421


250
δ 16.75 (d, 1H), 8.09 (s, 1H), 7.53 (m, 2H), 7.49 (m, 3H), 4.35 (m, 3H), 3.85 (m, 1H), 3.61 (m, 1H),



3.31 (m, 1H), 3.15 (m, 1H), 2.95 (m, 1H), 2.20-1.20 (m, 9H).


251
473


252
497


253
433


254
443


257
δ 16.60 (s, 1H), 7.94 (s, 1H), 4.32 (m, 2H), 3.02 (m, 2H), 2.74 (m, 2H), 2.45 (m, 2H), 2.06 (m, 2H),



1.85 (m, 4H), 1.8 (m, 2H).


 23Q
δ 8.80 (s, 1H), 7.46-7.66 (m, 5H), 6.04 (m, 1H), 5.86-5.98 (m, 1H), 5.26 (m, 1H), 5.02 (m, 1H), 4.62



(m, 2H), 2.69 (m, 2H), 2.42 (m, 2H), 2.12 (m, 2H).


 59Q
δ 8.78 (s, 1H), 7.49-7.57 (m, 5H), 6.03 (s, 1H), 4.28-4.39 (m, 2H), 3.94 (m, 1H), 3.59 (m, 1H), 3.33



(m, 1H), 2.68 (m, 2H), 2.45 (m, 2H), 2.12 (m, 2H), 1.99 (m, 1H), 1.76 (m, 1H), 1.57-1.66 (m, 1H),



1.39 (m, 1H).


 61Q
δ 8.81 (s, 1H), 7.77 (m, 2H), 7.57 (m, 3H), 6.04 (s, 1H), 4.69 (m, 2H), 2.69 (m, 2H), 2.46 (m, 3H),



2.12 (m, 2H).


 76Q
δ 8.91 (s, 1H), 7.60 (m, 3H), 7.56 (m, 1H), 7.28 (dd, 2H), 6.35 (dd, 1H), 6.03 (s, 1H), 5.75 (d, 1H),



2.66 (t, 2H), 2.44 (m, 2H), 2.09 (m, 2H).


 84Q
δ 8.71 (s, 1H), 6.80 (m, 2H), 6.78 (d, 1H), 6.01 (s, 1H), 5.34 (s, 2H), 3.86 (d, 6H), 2.8 (m, 2H), 2.75



(m, 2H), 2.45 (m, 2H), 2.20 (m, 2H), 1.80 (m, 2H), 1.00 (t, 3H).


105Q
δ 8.74 (s, 1H), 7.40 (m, 1H), 7.20 (m, 1H), 7.15 (m. 1H), 7.00 (s, 1H), 6.00 (s, 1H), 5.40 (s, 2H), 2.78



(m, 2H), 2.72 (m, 2H), 2.40 (m, 2H), 2.15 (m, 2H), 1.80 (m, 2H), 0.94 (m, 3H).


153Q
(300 MHz) δ 8.57 (s, 1H), 5.98 (s, 1H), 4.25-4.19 (m, 2H), 2.67-2.63 (m, 2H), 2.45-2.41 (m, 2H),



2.13-1.92 (m, 3H), 1.86-1.78 (m, 2H), 1.42-1.37 (m, 2H), 1.26-1.20 (m, 2H), 1.07-1.02 (m, 3H).


163Q
(500 MHz) δ 8.72 (s, 1H), 7.13-6.95 (m, 3H), 6.03 (s, 1H), 3.98 (d, 2H), 2.69 (td, 2H), 2.53-2.39 (m,



2H), 2.12 (quin, 2H), 1.75 (ddt, 1H), 1.66-1.57 (m, 3H), 1.50-1.43 (m, 2H), 1.19-0.99 (m, 3H), 0.77-



0.66 (m, 2H).


212Q
δ 8.86 (s., 1H), 7.07-7.32 (m, 4H), 6.80-7.06 (m, 4H), 6.04 (s., 1H), 3.78 (s, 3H), 2.67 (m, 2H), 2.44



(m, 2H), 2.27 (s, 3H), 2.11 (m, 2H).


257Q
δ 8.60 (s, 1H), 6.00 (s, 1H), 4.40 (m, 2H), 3.15 (m, 2H), 2.66 (m, 2H), 2.44 (m, 2H), 2.15 (m, 2H),



1.85 (m, 6H).


 23R
δ 9.03 (s, 1H), 7.42-7.76 (m, 5H), 5.82-6.04 (m, 1H), 5.42 (m, 1H), 5.04 (m, 1H), 4.72 (m, 2H).


 59R
δ 9.00 (s, 1H), 7.48-7.60 (m, 5H), 4.35 (m, 1H), 4.24-4.32 (m, 1H), 4.06 (m, 1H), 3.53-3.65 (m, 1H),



3.29-3.41 (m, 1H), 2.02 (m, 1H), 1.79 (m, 1H), 1.57-1.69 (m, 1H), 1.41 (m, 1H).


 61R
δ 13.02 (br s, 1H), 8.65 (s, 1H), 7.73 (m, 2H), 7.62 (m, 3H), 4.58 (m, 2H), 3.44 (m, 1H).


 76R
δ 12.64 (br s, 1H), 9.11 (s, 1H), 7.66 (m, 3H), 7.56 (d, 1H), 7.33 (m, 2H), 6.39 (dd, 1H), 5.93 (d, 1H).


 84R
δ 13.00 (br s, 1H), 8.92 (s, 1H), 6.80 (d, 1H), 6.79 (s, 1H), 6.85 (d, 1H), 5.34 (s, 2H), 3.87 (d, 6H),



2.80 (m, 2H), 1.80 (m, 2H), 1.01 (t, 3H).


105R
δ 12.8 (br s, 1H), 8.94 (s, 1H), 7.45 (m, 1H), 7.25 (m, 1H), 7.15 (m, 1H), 7.05 (s, 1H), 5.41 (s, 2H),



2.77 (m, 2H), 1.88 (m, 2H), 0.99 (t, 3H).


118R
δ 8.98 (s, 1H), 7.42 (m, 2H), 7.33 (m, 2H), 4.26 (m, 2H), 3.31 (t, 3H), 3.16 (s, 3H), 2.45 (s, 3H), 1.95



(m, 3H).


135R
δ 13.33 (s, 1H), 8.95 (s, 1H), 7.50 (d, 1H), 7.11 (d, 1H), 4.69 (m, 2H), 4.04 (s, 3H), 1.86 (m, 2H), 1.01



(t, 3H).


153R
(300 MHz) δ 13.15 (br s, 1H), 8.76 (s, 1H), 4.31-4.25 (m, 2H), 2.04-1.99 (m, 1H), 1.90-1.80 (m, 2H),



1.45-1.41 (m, 2H), 1.31-1.25 (m, 2H), 1.09 (t, 3H).


163R
(500 MHz) δ 12.77 (br s, 1H), 7.19-6.94 (m, 3H), 4.08 (d, 2H), 1.86-1.52 9m, 4H), 1.44 (d, 2H), 1.22-



0.95 (m, 3H), 0.82-0.63 (m, 2H).


164R
δ 13.12 (br s, 1H), 8.95 (s, 1H), 7.59 (m, 3H), 7.46 (m, 2H), 4.09 (s, 1H), 3.08 (d, 2H), 2.69 (d, 2H),



2.46 (m, 2H), 2.05 (m, 2H).


186R
δ 13.12 (br s, 1H), 8.93 (s, 1H), 7.83 (m, 1H), 7.58 (m, 1H), 7.29 (m, 1H), 4.56 (m, 1H), 4.09 (m, 2H),



3.26 (m, 2H), 3.12 (m, 2H), 1.67 (m, 2H).


212R
δ 9.09 (s, 1H), 6.98-7.21 (m, 6H), 6.90 (d, 2H), 3.81 (s, 3H), 2.28 (s, 3H).


216R
δ 13.25 (br s, 1H), 8.93 (s, 1H), 7.67 (m, 2H), 7.48 (m, 2H), 4.06 (m, 1H), 3.28 (s, 1H), 2.68 (dd, 2H),



1.85 (d, 2H), 1.73 (d, 2H), 1.63 (m, 1H), 1.24 (m, 1H), 1.05 (m, 2H).


242R
δ 13.14 (br s, 1H), 9.03 (s, 1H), 8.05 (m, 2H), 7.96 (d, 2H), 7.65 (ddd, 2H), 7.56 (dd, 1H), 4.14 (m,



2H), 1.75 (m, 2H), 0.80 (t, 3H).


247R
δ 13.26 (br s, 1H), 8.96 (s, 1H), 7.57 (m, 3H), 7.46 (m, 2H), 4.45 (m, 1H), 2.32 (m, 2H), 1.99 (m, 2H),



1.18 (m, 15H), 0.69 (m, 3H).


257R
δ 13.00 (br s, 1H), 8.75 (s, 1H), 4.42 (m, 2H), 3.10 (m, 2H), 1.82 (m, 6H)


 23S
δ 8.70 (s, 1H), 7.49-7.53 (m, 5H), 5.85-5.97 (m, 1H), 5.25 (m, 1H), 4.95 (m, 1H), 4.59 (m, 2H), 4.41



(m, 2H), 1.40 (m, 3H).


 59S
δ 8.68 (s, 1H), 7.46-7.55 (m, 5H), 4.40 (m, 2H), 4.28-4.35 (m, 2H), 3.88 (m, 1H), 3.58 (m, 1H), 3.31



(m, 1H), 1.91-2.02 (m, 1H), 1.52-1.81 (m, 4H), 1.39 (m, 3H).


 61S
δ 8.72 (s, 1H), 7.76 (m, 2H), 7.55 (m, 3H), 4.66 (m, 2H), 4.42 (m, 2H), 2.41 (s, 1H), 1.42 (m, 3H).


 84S
δ 8.62 (s, 1H), 6.81 (m, 2H), 6.70 (m, 1H), 5.29 (s, 2H), 4.39 (q, 2H), 3.86 (d, 6H), 2.76 (t, 2H), 1.73



(m, 2H), 1.40 (t, 3H), 0.98 (t, 3H).


105S
δ 8.64 (s, 1H), 7.42 (m, 1H), 7.20 (m, 1H), 7.18 (m, 1H), 7.00 (s, 1H), 5.34 (s, 2H), 4.39 (m, 2H), 2.65



(m, 2H), 1.75 (m, 2H), 1.40 (m, 3H), 0.95 (t, 3H).


118S
δ 8.66 (s, 1H), 7.38 (m, 2H), 7.29 (m, 2H), 4.40 (m, 2H), 4.11 (m, 2H), 3.30 (t, 2H), 3.15 (s, 3H), 2.43



(s, 3H), 1.93 (m, 2H), 1.40 (t, 3H).


135S
δ 8.68 (s, 1H), 7.47 (d, 1H), 6.98 (d, 1H), 4.53 (m, 2H), 4.39 (q, 2H), 4.02 (s, 3H), 1.82 (m, 2H), 1.39



(t, 3H), 0.96 (t, 3H).


153S
(300 MHz) δ 8.51 (s, 1H), 4.23-4.18 (m, 2H), 3.88 (s, 3H), 1.99-1.95 (m, 1H), 1.85-1.77 (m, 2H),



1.36-1.32 (m, 2H), 1.21-1.17 (m, 2H), 1.03 (t, 3H).


163S
(500 MHz) δ 8.62 (s, 1H), 7.06-6.98 (m, 3H), 4.40 (q, 2H), 3.95 (d, 2H), 1.80-1.70 (m, 1H), 1.66-1.55



(m, 3H), 1.46 (d, 2H), 1.40 (t, 3H), 1.17-0.96 (m, 3H), 0.70 (dd, 2H).


164S
δ 8.59 (s, 1H), 7.55 (m, 3H), 7.42 (m, 2H), 4.40 (q, 2H), 3.92 (m, 1H), 3.10 (d, 2H), 2.64 (d, 2H), 2.41



(m, 2H), 1.98 (m, 2H), 1.40 (t, 3H).


186S
δ 8.57 (s, 1H), 7.71 (m, 1H), 7.52 (m, 1H), 7.24 (m, 1H), 4.39 (m, 3H), 4.04 (d, 2H), 3.17 (m, 4H),



1.58 (m, 3H), 1.39 (t, 3H).


212S
δ 8.80 (s, 1H), 7.14-7.25 (m, 1H), 6.95-7.18 (m, 5 H), 6.82-6.92 (m, 2H), 3.94 (s, 3H), 3.78 (s, 3H),



2.26 (s, 3H).


216S
δ 8.57 (s, 1H), 7.64 (m, 2H), 7.43 (m, 2H), 4.40 (q, 2H), 3.89 (m, 1H), 3.24 (s, 1H), 2.75 (dd, 2H),



1.78 (d, 2H), 1.63 (m, 3H), 1.55 (d, 1H), 1.39 (t, 3H), 0.99 (m, 2H).


242S
δ 8.71 (s, 1H), 7.99 (m, 2H), 7.93 (d, 2H), 7.62 (m, 2H), 7.53 (dd, 1H), 4.42 (q, 2H), 4.01 (m, 2H),



1.71 (m, 2H), 1.42 (t, 3H), 0.75 (t, 3H).


247S
δ 8.60 (s, 1H), 7.51 (m, 3H), 7.42 (m, 2H), 4.39 (q, 2H), 4.12 (m, 1H), 2.32 (m, 2H), 1.98 (m, 2H),



1.39 (t, 3H), 1.18 (m, 12H), 1.02 (m, 3H), 0.66 (m, 3H).


257S
δ 8.47 (s, 1H), 4.34 (m, 4H), 3.02 (m, 2H), 1.82 (m, 6H), 1.36 (m, 3H).






aMass 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, observed by mass spectrometry using atmospheric pressure chemical ionization (AP+) unless otherwise noted.



b1H NMR data are reported in CDCl3 at 400 MHz unless otherwise noted; s means singlet, br s means broad singlet, d means doublet, dd means doublet of doublet, ddd means doublet of double of doublets, ddt means doublet of doublet of triplets, t means triplet, td means triplet of doublets, q means quartet, quin means quintet and sxt means sextet.






Biological Examples of the Invention

Test A


Seeds of barnyardgrass (Echinochloa crus-galli), large crabgrass (Digitaria sanguinalis), giant foxtail (Setaria faberii), 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 these species were also treated with postemergence applications of test compounds formulated in the same manner.


Plants ranged in height from two to ten 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 ten days, 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







Postemergence










1000 g ai/ha
500 g ai/ha



Compound
Compounds



































217
1
2
3
4
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28





Barnyardgrass
90
60
100
90
100
70
100
100
90
100
90
90
80
40
60
70
90
70
10
10
70
60
70
90
80
90
90


Corn
40
0
90
10
50
40
50
70
90
20
80
50
20
10
20
10
20
10
10
0
40
0
30
20
20
30
0


Crabgrass, Large
100
80
100
90
90
70
90
90
100
90
100
90
90
70
40
70
80
20
10
10
80
60
90
90
90
100
80


Foxtail, Giant
80
40
100
60
90
60
100
90
100
90
90
80
90
70
70
30
90
50
0
0
80
50
90
90
90
90
80


Morningglory
100
90
100
90
100
100
100
90
100
90
100
50
100
50
20
70
100
60
10
0
100
100
100
90
80
70
10


Pigweed
100
80
100
100
100
100
100
100
100
100
100
100
100
90
70
100
100
100
50
50
100
100
100
100
100
100
100


Velvetleaf
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
70
70
100
100
100
100
100
100
100


Wheat
40
20
20
10
60
40
50
40
60
0
0
60
0
20
10
10
50
0
0
0
0
0
30
0
0
0
0












500 g ai/ha



Compounds


































29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54





Barnyardgrass
90
30
80
80
100
100
60
100
90
90
90
90
90
90
90
100
100
90
100
90
90
100
90
90
100
60


Corn
10
0
20
10
20
30
10
60
40
60
40
50
10
30
50
40
20
20
70
30
20
30
80
70
80
10


Crabgrass, Large
90
60
90
90
100
100
80
100
100
100
90
100
70
80
90
90
90
90
100
100
90
90
100
100
100
70


Foxtail, Giant
90
40
90
90
100
100
80
100
90
90
90
100
80
70
80
90
90
90
100
100
80
90
90
100
90
60


Morningglory
90
50
70
100
90
100
80
100
100
100
90
100
70
80
80
90
100
70
100
100
100
80
100
100
100
100


Pigweed
100
80
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100


Velvetleaf
100
—
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100


Wheat
0
0
0
30
20
30
0
0
0
40
0
0
0
0
0
20
40
0
0
20
0
0
0
40
50
0












500 g ai/ha



Compounds


































55
56
57
58
59
60
61
62
63
64
65
66
67
68
69
70
71
72
73
74
75
76
77
78
79
80





Barnyardgrass
70
90
90
90
90
90
90
90
90
90
50
90
90
90
100
80
60
90
90
90
90
80
90
70
90
80


Corn
10
50
40
20
30
10
10
70
50
60
0
60
10
10
40
20
20
10
60
20
50
20
20
20
60
50


Crabgrass, Large
90
90
90
90
100
100
90
90
90
90
60
90
90
100
100
90
80
90
90
90
90
90
80
70
90
90


Foxtail, Giant
60
90
90
90
90
90
80
90
80
80
40
80
60
70
90
90
60
60
90
80
90
70
70
50
80
90


Morningglory
90
100
60
100
100
90
100
100
100
100
60
90
100
90
100
100
100
90
100
100
100
90
100
100
100
100


Pigweed
100
100
100
100
100
100
100
100
100
100
60
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100


Velvetleaf
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100


Wheat
0
0
10
0
10
50
0
20
0
30
0
0
30
0
10
0
0
0
50
20
50
10
0
0
50
0












500 g ai/ha



Compounds


































81
82
83
84
85
86
87
88
89
90
91
92
93
94
95
96
97
98
99
100
101
102
103
104
105
106





Barnyardgrass
100
70
90
10
90
90
90
90
90
90
100
90
90
90
90
90
90
90
90
90
90
90
60
40
50
50


Corn
70
20
30
20
80
50
50
60
10
20
10
20
30
10
10
20
80
60
20
0
10
20
20
0
10
10


Crabgrass, Large
90
90
90
10
90
90
90
90
100
90
100
90
100
90
90
100
100
100
100
90
90
100
40
0
70
70


Foxtail, Giant
90
80
90
0
90
90
90
90
90
80
80
90
90
80
90
90
80
90
90
90
80
90
20
0
20
60


Morningglory
100
100
100
90
100
90
100
100
100
100
100
100
100
100
100
100
100
100
100
100
70
100
100
100
80
100


Pigweed
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100


Velvetleaf
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
80
100
100


Wheat
30
0
0
0
40
50
60
0
20
40
50
0
0
0
0
20
20
20
0
30
0
10
0
0
0
0












500 g ai/ha



Compounds


































107
108
109
110
111
112
113
114
115
116
117
118
119
120
121
122
123
124
125
126
127
128
129
130
131
132





Barnyardgrass
90
90
90
90
90
90
90
90
90
100
90
90
90
90
100
80
90
90
90
90
90
100
100
100
90
90


Corn
50
40
30
10
30
20
60
50
20
10
50
30
70
50
40
30
70
20
20
60
20
60
50
50
30
40


Crabgrass, Large
90
90
100
90
90
90
100
90
90
80
100
90
90
100
100
90
90
90
90
90
90
90
90
100
90
70


Foxtail, Giant
90
90
90
50
90
80
100
80
80
90
80
90
90
90
90
80
80
70
90
80
80
90
90
90
90
70


Morningglory
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
80
100
100
100
100
100
100
90


Pigweed
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
90


Velvetleaf
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100


Wheat
10
0
0
0
0
10
60
0
0
0
30
10
60
70
60
50
20
0
10
20
0
20
20
30
0
30












500 g ai/ha



Compounds


































133
134
135
136
138
139
140
141
142
143
144
145
146
147
148
149
150
151
152
153
154
155
156
157
158
159





Barnyardgrass
90
60
30
80
90
80
90
90
90
90
100
100
100
90
100
90
80
90
100
90
90
100
90
100
90
100


Corn
40
20
0
0
20
40
20
30
20
20
30
40
30
30
60
30
0
10
50
20
10
40
20
30
50
70


Crabgrass, Large
100
80
70
90
90
80
90
90
90
90
90
90
90
90
90
70
50
70
100
90
100
90
80
100
100
90


Foxtail, Giant
90
70
0
50
90
80
90
90
80
80
90
80
90
80
90
80
70
70
100
80
90
90
90
100
90
100


Morningglory
70
60
90
100
100
100
100
100
100
100
70
90
90
100
100
100
100
100
100
60
70
100
100
30
100
100


Pigweed
100
80
90
100
100
100
100
100
100
90
90
100
100
100
100
100
60
100
100
100
100
100
100
100
100
100


Velvetleaf
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
90
100
100
100
100
100
100
100
100
100


Wheat
40
0
0
0
20
40
0
0
20
10
0
0
50
60
0
50
20
20
70
10
0
30
20
0
50
60












500 g ai/ha



Compounds


































160
161
162
163
164
165
166
167
168
169
170
171
172
173
174
175
176
177
178
179
180
181
182
183
184
185





Barnyardgrass
100
90
100
100
100
80
100
100
100
100
90
90
90
100
100
100
90
100
90
90
100
100
90
90
100
90


Corn
60
10
50
20
50
30
40
30
30
30
30
40
30
20
20
20
10
0
70
80
40
50
20
80
80
50


Crabgrass, Large
90
90
100
90
100
50
90
90
90
100
90
90
80
90
90
80
60
70
80
100
100
90
90
100
100
70


Foxtail, Giant
80
90
100
50
100
30
90
90
90
100
80
90
90
90
60
80
70
40
80
90
100
100
80
100
100
80


Morningglory
100
100
100
100
100
100
—
100
100
100
100
100
100
100
60
80
50
10
100
100
100
100
100
70
100
100


Pigweed
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
80
100
100
100
100
100
100
100


Velvetleaf
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
90
100
100
100
100
100
100
100
100
100


Wheat
50
0
50
0
20
0
0
0
50
20
20
50
20
60
0
0
0
0
30
80
30
60
50
80
50
0












500 g ai/ha



Compounds


































186
187
188
189
190
191
192
193
194
195
196
197
198
199
200
202
203
204
205
206
207
208
209
210
211
212





Barnyardgrass
90
100
90
90
100
100
90
100
100
90
90
100
100
100
10
100
100
100
100
100
90
90
100
90
100
100


Corn
60
50
10
40
0
50
40
40
10
20
40
50
30
50
0
30
30
10
20
0
30
20
40
0
20
0


Crabgrass, Large
90
100
90
90
90
100
80
100
90
90
90
100
100
100
10
100
70
100
90
100
90
80
100
30
80
30


Foxtail, Giant
90
90
80
90
90
100
70
100
50
70
100
100
90
100
10
100
80
100
90
90
90
80
100
70
80
40


Morningglory
100
100
100
100
100
100
70
100
100
—
100
100
100
100
60
100
100
100
100
100
80
100
100
100
100
100


Pigweed
100
100
100
100
100
90
80
100
100
100
100
100
100
100
80
100
100
100
100
100
100
90
100
100
90
100


Velvetleaf
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
70
70
70


Wheat
0
0
0
0
0
50
0
70
0
0
30
0
0
10
0
50
30
40
10
0
0
10
0
10
0
0












500 g ai/ha



Compounds


































213
214
215
216
218
219
220
221
222
223
224
225
226
227
228
229
230
231
232
233
234
235
236
237
238
239





Barnyardgrass
100
90
100
90
90
90
90
20
80
50
90
100
90
90
90
100
90
90
90
90
100
100
90
100
100
90


Corn
20
30
30
0
70
30
30
20
0
20
50
50
60
60
90
40
20
40
60
80
50
90
50
80
80
30


Crabgrass, Large
50
90
70
80
70
100
90
20
30
60
100
100
100
100
100
100
90
70
60
90
90
100
90
100
100
90


Foxtail, Giant
40
90
80
70
70
90
60
10
40
70
100
90
90
90
90
100
50
80
90
90
90
100
90
100
100
80


Morningglory
100
100
100
90
100
100
100
20
40
80
100
100
100
100
100
100
90
100
100
100
100
100
100
100
100
100


Pigweed
100
100
100
90
100
100
100
70
70
70
100
100
100
100
100
100
90
90
90
100
90
100
100
100
100
90


Velvetleaf
60
100
100
100
100
100
100
80
90
80
100
100
100
100
100
100
100
100
80
100
100
100
100
100
100
100


Wheat
0
20
0
30
0
30
20
0
0
0
60
40
50
0
20
20
0
0
50
60
20
80
40
70
80
0













500 g ai/ha
125 g ai/ha



Compounds
Compounds


































240
241
242
243
244
245
246
247
248
249
250
251
252
253
254
255
256
1
2
3
4
7
8
9
10
11





Barnyardgrass
100
90
90
100
100
100
100
80
100
100
100
100
90
100
90
100
90
20
100
50
90
30
90
80
90
40


Corn
80
50
20
90
80
90
90
30
30
20
70
20
10
40
10
70
10
0
30
0
10
0
10
10
30
0


Crabgrass, Large
100
70
60
90
90
90
100
70
80
100
100
90
60
100
70
100
80
50
90
90
70
50
80
70
90
50


Foxtail, Giant
100
90
80
100
90
100
100
30
100
90
100
90
60
100
50
90
70
10
90
30
80
40
90
80
90
70


Morningglory
100
100
100
100
100
100
100
100
100
100
100
100
100
100
50
100
80
70
90
80
100
100
90
80
100
90


Pigweed
100
80
30
100
100
100
100
90
90
100
100
80
90
100
90
100
100
70
100
100
100
80
100
100
100
90


Velvetleaf
100
100
90
100
100
100
100
100
100
100
100
100
90
100
90
100
100
100
100
100
100
100
100
100
100
100


Wheat
40
60
30
90
70
80
50
0
0
50
20
10
10
20
0
50
0
10
0
0
0
0
10
0
40
0












125 g ai/ha



Compounds



































12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38





Barnyardgrass
90
30
30
10
20
10
20
0
0
0
10
10
10
30
30
50
30
20
10
10
20
80
90
10
90
50
60


Corn
40
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Crabgrass, Large
90
30
30
20
10
10
30
0
0
0
40
30
70
40
70
70
40
70
30
50
50
70
90
50
80
70
60


Foxtail, Giant
90
30
30
10
30
0
40
20
0
0
30
10
70
50
50
80
30
70
10
70
30
60
90
40
80
70
50


Morningglory
100
0
20
10
10
20
40
0
0
0
30
50
70
50
50
60
0
60
30
20
50
80
80
—
50
80
100


Pigweed
100
80
80
60
50
80
100
80
10
0
80
80
90
80
90
100
100
80
70
70
100
90
100
80
90
100
100


Velvetleaf
100
100
100
100
70
100
100
100
20
30
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100


Wheat
0
10
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0












125 g ai/ha



Compounds


































39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
61
62
63
64





Barnyardgrass
60
90
50
60
70
90
90
80
90
80
60
90
90
90
90
10
50
90
70
50
90
60
70
80
70
50


Corn
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
10
0
0
10
0
0
30
10
0


Crabgrass, Large
80
90
20
60
70
80
60
70
90
90
90
90
90
90
90
40
70
80
80
80
90
90
80
70
80
80


Foxtail, Giant
80
90
20
40
60
80
50
60
90
90
50
90
90
90
90
10
20
80
80
70
80
80
50
70
60
60


Morningglory
80
50
10
80
20
80
80
60
80
90
100
80
100
100
100
40
90
90
50
80
100
60
100
100
100
90


Pigweed
100
100
100
100
100
100
90
80
90
100
100
100
100
90
100
100
90
90
90
100
100
100
100
90
90
90


Velvetleaf
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100


Wheat
0
0
0
0
0
0
0
0
0
0
0
0
0
0
30
0
0
0
0
0
0
20
0
0
0
0












125 g ai/ha



Compounds


































65
66
67
68
69
70
71
72
73
74
75
76
77
78
79
80
81
82
83
84
85
86
87
88
89
90





Barnyardgrass
10
80
70
80
90
50
0
80
70
80
80
50
80
50
80
30
100
10
70
0
90
90
80
80
90
80


Corn
0
—
—
0
20
0
0
0
30
0
0
0
0
0
10
0
10
0
0
0
10
0
10
0
0
0


Crabgrass, Large
30
70
60
80
80
50
30
80
90
90
90
70
60
30
80
70
90
40
80
0
90
90
90
90
90
80


Foxtail, Giant
10
70
30
50
80
50
20
40
80
40
80
40
50
20
50
70
80
10
70
0
70
80
70
60
60
70


Morningglory
50
90
100
90
100
100
80
90
100
90
90
90
90
70
100
100
90
90
100
90
100
90
90
90
100
100


Pigweed
20
100
100
100
100
100
70
80
100
100
100
90
100
100
100
100
100
90
90
100
100
100
100
100
100
100


Velvetleaf
90
100
100
100
100
100
100
100
100
90
100
100
100
100
100
100
100
100
100
70
100
100
100
100
100
100


Wheat
0
0
20
0
0
0
0
0
10
0
0
0
0
0
0
0
0
0
0
0
0
0
30
0
0
0












125 g ai/ha



Compounds


































91
92
93
94
95
96
97
98
99
100
101
102
103
104
105
106
107
108
109
110
111
112
113
114
115
116





Barnyardgrass
90
80
90
90
80
90
90
80
90
80
80
80
30
10
20
10
90
90
80
60
90
60
70
70
70
80


Corn
0
0
10
0
0
0
50
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
10
0
0


Crabgrass, Large
90
90
90
80
90
90
80
90
90
80
90
90
10
0
20
40
80
90
90
80
90
80
100
80
60
60


Foxtail, Giant
80
80
80
30
70
70
60
70
80
80
60
80
0
0
0
20
70
60
70
10
60
70
90
60
50
60


Morningglory
100
100
100
100
100
100
100
100
100
90
60
100
100
70
10
100
100
100
90
90
100
90
100
90
90
100


Pigweed
100
100
100
100
100
100
100
100
100
90
90
100
100
100
90
80
100
100
100
90
100
90
100
100
100
100


Velvetleaf
100
100
100
100
100
100
100
100
100
100
100
100
100
70
100
100
100
100
100
90
100
100
100
100
100
70


Wheat
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0












125 g ai/ha



Compounds


































117
118
119
120
121
122
123
124
125
126
127
128
129
130
131
132
133
134
135
136
138
139
140
141
142
143





Barnyardgrass
80
90
80
90
80
60
80
40
70
80
80
100
90
100
90
10
20
10
10
30
90
60
90
90
70
70


Corn
20
0
0
10
0
0
20
0
0
10
20
20
20
10
0
0
10
0
0
0
20
20
0
20
0
10


Crabgrass, Large
80
90
80
90
80
70
80
70
70
90
80
90
90
70
90
20
40
50
40
80
70
70
90
80
70
70


Foxtail, Giant
70
80
70
80
90
70
70
50
70
70
70
90
90
80
80
0
20
40
0
30
60
50
80
80
30
60


Morningglory
100
100
90
100
100
90
100
100
80
100
90
100
100
100
100
90
40
0
70
100
50
100
100
70
100
90


Pigweed
100
100
100
90
100
100
100
90
90
90
90
100
100
100
100
60
80
70
80
80
100
90
90
90
90
70


Velvetleaf
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100


Wheat
0
0
50
20
30
0
0
0
0
0
0
0
0
0
0
0
20
0
0
0
0
20
0
0
0
0












125 g ai/ha



Compounds


































144
145
146
147
148
149
150
151
152
153
154
155
156
157
158
159
160
161
162
163
164
165
166
167
168
169





Barnyardgrass
70
70
100
80
90
70
40
60
100
80
90
90
90
90
90
90
90
30
100
50
100
0
80
60
30
90


Corn
0
30
20
20
0
0
0
0
0
0
0
20
20
0
10
0
20
0
0
0
10
0
30
30
20
0


Crabgrass, Large
50
70
80
80
70
40
20
30
90
90
70
70
70
80
70
90
90
60
80
60
90
20
40
60
50
90


Foxtail, Giant
40
60
70
70
60
60
40
20
80
70
60
80
80
90
70
90
70
40
70
20
100
20
60
90
50
80


Morningglory
30
90
90
100
100
100
100
40
100
50
30
100
100
10
70
100
100
60
100
10
100
50
100
60
100
100


Pigweed
80
100
100
100
90
70
30
100
100
100
60
100
100
90
100
100
100
80
100
80
100
80
70
90
100
100


Velvetleaf
100
100
100
100
100
100
50
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100


Wheat
0
0
20
20
0
20
0
0
20
0
0
0
0
0
0
10
0
0
30
0
0
0
0
0
0
20












125 g ai/ha



Compounds


































170
171
172
173
174
175
176
177
178
179
180
181
182
183
184
185
186
187
188
189
190
191
192
193
194
195





Barnyardgrass
40
50
90
90
90
50
50
80
80
60
90
100
70
60
90
70
80
90
70
90
90
90
60
90
90
70


Corn
20
30
20
0
10
0
0
0
0
10
10
10
0
10
10
0
0
0
0
10
0
0
0
10
0
0


Crabgrass, Large
60
60
60
70
70
40
10
30
50
60
90
90
80
80
80
50
90
90
80
90
90
70
30
100
60
40


Foxtail, Giant
50
60
60
70
20
30
10
0
50
40
70
100
50
80
90
50
80
80
40
80
80
80
50
90
30
30


Morningglory
100
100
90
100
30
10
0
0
50
60
40
30
100
40
50
100
100
100
90
100
100
90
—
100
90
60


Pigweed
80
100
100
100
100
100
100
100
60
90
100
100
80
100
100
90
100
100
90
100
100
80
60
100
100
90


Velvetleaf
100
100
100
100
100
100
80
90
90
100
100
100
100
100
100
90
100
100
100
100
100
100
70
100
100
100


Wheat
0
20
0
0
0
0
0
0
0
40
0
30
0
50
0
0
0
0
0
0
0
0
0
40
0
0












125 g ai/ha



Compounds


































196
197
198
199
200
202
203
204
205
206
207
208
209
210
211
212
213
214
215
216
218
219
220
221
222
223





Barnyardgrass
80
80
70
90
0
90
80
100
90
90
60
30
80
40
50
50
20
80
90
10
80
90
90
10
10
0


Corn
10
20
0
0
0
10
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Crabgrass, Large
50
70
70
70
10
70
30
60
60
60
60
30
50
10
40
10
20
80
40
40
20
80
50
10
0
0


Foxtail, Giant
70
80
60
100
0
80
30
30
40
50
60
30
60
10
50
0
10
50
40
30
40
50
20
0
0
0


Morningglory
100
100
100
100
50
100
100
30
100
100
40
50
30
50
70
50
60
80
100
70
80
100
100
10
30
60


Pigweed
80
100
90
100
60
100
100
100
90
90
100
80
60
90
70
100
80
90
90
90
100
100
100
40
40
50


Velvetleaf
100
100
100
100
100
100
90
100
100
100
100
100
100
70
60
70
70
100
100
90
100
100
100
80
60
50


Wheat
0
0
0
0
0
20
0
0
0
0
0
0
0
0
0
0
0
0
0
20
0
0
0
0
0
0












125 g ai/ha



Compounds


































224
225
226
227
228
229
230
231
232
233
234
235
236
237
238
239
240
241
242
243
244
245
246
247
248
249





Barnyardgrass
90
90
90
90
90
90
70
70
60
90
80
90
90
100
100
90
100
90
50
100
90
90
70
30
90
90


Corn
10
10
10
10
50
0
0
0
10
60
20
80
20
40
40
30
40
20
0
70
40
40
0
0
0
0


Crabgrass, Large
70
90
90
90
90
80
80
50
20
90
40
100
80
80
90
80
90
50
20
90
90
90
70
40
50
90


Foxtail, Giant
70
70
90
90
90
90
30
60
60
90
70
90
70
90
90
70
90
80
50
100
90
100
80
0
50
80


Morningglory
100
100
100
100
100
100
70
90
100
100
100
100
100
100
100
100
100
100
40
100
100
100
90
100
100
100


Pigweed
100
100
100
100
100
100
80
80
70
100
70
100
80
90
100
80
90
70
20
100
100
100
90
70
80
90


Velvetleaf
100
100
100
100
100
100
100
90
70
100
100
100
100
100
100
100
100
100
50
100
100
100
100
100
100
100


Wheat
0
0
0
0
0
0
0
0
20
20
0
50
0
20
50
0
20
40
0
70
40
40
0
0
0
10














125 g ai/ha




Compounds

















250
251
252
253
254
255
256







Barnyardgrass
50
80
80
100
0
90
40



Corn
0
0
0
10
0
30
0



Crabgrass, Large
60
50
30
80
20
90
30



Foxtail, Giant
90
50
40
60
10
90
20



Morningglory
100
100
80
100
20
100
30



Pigweed
100
70
70
90
60
90
90



Velvetleaf
100
100
70
100
50
100
100



Wheat
0
0
0
0
0
10
0











Preemergence










1000 g ai/ha
500 g ai/ha



Compound
Compounds



































217
1
2
3
4
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28





Barnyardgrass
80
10
70
60
70
10
80
100
90
70
70
90
70
90
70
80
100
90
20
0
100
70
90
80
60
80
70


Corn
0
0
0
0
20
0
20
0
0
0
0
20
0
0
20
0
20
0
0
0
0
0
0
0
0
0
0


Crabgrass, Large
100
70
100
80
90
40
100
100
100
90
90
100
90
90
70
100
100
80
30
20
90
90
100
100
90
90
60


Foxtail, Giant
80
10
90
10
70
20
90
90
100
50
90
90
90
70
70
20
90
30
20
10
80
20
100
90
70
90
30


Morningglory
70
50
90
100
70
40
70
90
90
70
90
0
60
60
0
10
70
50
0
0
70
70
80
60
70
80
80


Pigweed
100
100
100
100
90
80
90
100
100
100
100
100
100
90
50
90
100
90
—
70
90
70
100
80
100
90
100


Velvetleaf
100
80
100
90
100
100
90
100
100
100
90
100
100
90
40
100
100
100
50
0
100
100
100
100
100
100
80


Wheat
30
0
0
0
20
0
20
0
50
0
0
40
0
20
0
0
40
0
0
0
0
0
20
20
0
0
0












500 g ai/ha



Compounds




































29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56





Barnyardgrass
100
40
40
90
90
100
0
50
30
90
90
100
80
60
80
100
80
50
90
100
60
90
90
100
100
10
10
90


Corn
0
0
0
0
30
0
0
0
0
30
0
0
0
0
0
0
0
0
0
0
0
0
0
10
0
0
0
0


Crabgrass, Large
100
60
90
90
100
100
60
80
50
100
90
100
80
90
100
90
100
80
100
100
90
100
100
100
100
30
50
90


Foxtail, Giant
100
10
40
90
90
100
10
60
50
80
90
90
30
40
70
90
80
60
90
90
50
80
100
100
100
0
0
90


Morningglory
80
60
50
80
50
60
20
30
30
70
60
80
20
50
10
70
90
70
90
80
80
80
90
90
90
0
60
90


Pigweed
100
80
80
100
90
100
100
80
100
100
90
90
90
100
100
90
100
90
100
100
90
100
100
100
100
90
100
100


Velvetleaf
100
70
70
70
80
100
70
100
90
100
90
100
80
100
100
100
100
70
100
100
90
90
90
100
90
70
60
100


Wheat
0
0
0
20
10
0
0
20
0
20
0
0
0
0
0
0
20
20
0
0
0
0
0
0
10
0
0
0












500 g ai/ha



Compounds



































57
58
59
60
61
62
63
64
65
66
67
68
69
70
71
72
73
74
75
76
77
78
79
80
81
82
83





Barnyardgrass
90
90
90
90
90
90
90
90
10
70
40
50
60
10
0
60
70
60
80
30
50
30
70
10
90
10
90


Corn
0
0
0
10
0
20
0
0
0
0
0
0
0
0
0
20
0
0
0
0
0
0
0
0
0
0
20


Crabgrass, Large
100
90
100
100
100
90
100
90
80
100
90
100
100
90
50
100
100
90
100
100
90
50
100
90
100
100
100


Foxtail, Giant
90
80
80
90
60
70
80
70
40
80
50
60
70
60
10
30
70
40
70
30
20
10
50
60
80
40
90


Morningglory
80
100
90
80
80
100
70
0
0
30
50
50
50
10
0
70
80
60
90
50
70
0
50
30
70
60
60


Pigweed
100
100
100
100
90
100
100
100
0
100
90
100
100
100
90
90
100
100
100
100
90
100
100
90
100
100
100


Velvetleaf
100
100
100
100
100
90
90
90
50
100
80
100
100
80
70
100
100
90
100
70
100
50
100
100
100
90
100


Wheat
0
0
0
40
0
10
0
0
0
0
0
0
10
0
0
0
30
0
0
20
0
0
30
0
20
0
30












500 g ai/ha



Compounds


































84
85
86
87
88
89
90
91
92
93
94
95
96
97
98
99
100
101
102
103
104
105
106
107
108
109





Barnyardgrass
0
100
100
90
90
80
70
100
100
100
30
80
100
100
60
90
90
70
90
20
0
0
50
90
90
70


Corn
0
10
—
0
0
0
0
0
0
0
0
0
10
0
0
0
0
0
0
0
0
0
0
—
0
0


Crabgrass, Large
0
100
—
100
—
90
100
100
100
100
90
90
100
100
100
100
90
90
100
80
0
50
80
100
90
90


Foxtail, Giant
0
90
100
80
100
70
60
70
80
80
40
60
80
90
80
80
80
50
100
60
0
50
70
90
40
30


Morningglory
10
80
60
80
70
70
70
80
80
90
40
90
80
80
80
80
80
80
80
60
0
—
80
100
90
70


Pigweed
100
—
—
—
—
100
100
90
100
100
100
100
100
100
100
100
100
80
100
100
90
90
90
100
100
100


Velvetleaf
40
—
100
100
100
100
100
100
100
100
70
100
100
100
100
100
80
100
100
90
40
70
60
100
90
100


Wheat
0
40
—
40
10
30
0
20
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0












500 g ai/ha



Compounds


































110
111
112
113
114
115
116
117
118
119
120
121
122
123
124
125
126
127
128
129
130
131
132
133
134
135





Barnyardgrass
60
90
80
90
90
80
70
90
90
100
100
100
100
100
60
90
100
100
100
100
90
100
100
100
10
0


Corn
0
0
0
—
0
0
0
20
0
30
30
30
0
30
0
0
20
0
0
0
30
0
20
20
0
0


Crabgrass, Large
80
100
100
100
100
80
70
100
90
100
100
100
100
100
90
100
100
100
100
90
100
100
100
100
30
40


Foxtail, Giant
10
70
60
90
80
70
60
70
50
100
100
100
100
100
40
80
90
90
90
80
90
80
90
80
30
0


Morningglory
70
80
80
80
80
80
40
90
70
90
90
70
80
—
80
0
90
80
—
90
80
80
30
0
30
50


Pigweed
90
100
100
100
100
100
100
100
100
100
100
100
100
100
100
90
100
100
100
100
100
100
80
100
60
80


Velvetleaf
70
100
70
100
100
90
60
90
80
100
100
100
100
100
100
100
100
100
100
90
90
100
80
100
70
70


Wheat
0
0
0
0
20
0
0
20
0
60
70
50
40
20
0
0
20
0
30
0
0
0
10
20
0
0












500 g ai/ha



Compounds


































136
138
139
140
141
142
143
144
145
146
147
148
149
150
151
152
153
154
155
156
157
158
159
160
161
162





Barnyardgrass
60
90
90
100
100
80
90
20
90
100
100
30
50
0
100
100
80
40
90
80
50
80
90
80
90
100


Corn
0
20
20
0
0
0
0
0
20
30
0
0
20
0
0
30
20
0
30
20
0
20
40
20
0
0


Crabgrass, Large
60
70
100
90
100
80
90
30
100
100
100
50
80
10
50
100
100
50
90
50
70
100
100
100
90
100


Foxtail, Giant
0
70
70
90
80
20
70
10
70
90
90
10
60
0
60
90
70
30
60
50
50
80
90
70
80
90


Morningglory
60
0
80
50
30
50
70
10
80
—
90
0
40
0
30
80
70
0
0
0
0
80
50
—
40
80


Pigweed
100
90
100
100
100
100
90
90
100
100
100
60
100
0
70
100
100
80
90
80
50
100
100
100
100
100


Velvetleaf
100
80
90
100
100
60
100
70
100
100
100
80
70
0
70
100
100
80
100
50
100
80
100
30
90
100


Wheat
0
20
10
0
0
0
0
0
20
40
20
0
20
0
20
50
20
0
0
0
0
10
20
20
0
50












500 g ai/ha



Compounds


































163
164
165
166
167
168
169
170
171
172
173
174
175
176
177
178
179
180
181
182
183
184
185
186
187
188





Barnyardgrass
20
80
0
20
30
20
50
60
70
80
60
40
30
30
10
50
70
80
100
90
100
90
50
60
90
30


Corn
0
0
0
0
0
0
20
0
20
0
10
20
0
0
20
0
0
0
0
20
0
20
0
0
0
0


Crabgrass, Large
10
90
0
70
90
80
40
70
100
90
100
60
50
20
10
70
100
100
100
100
100
100
30
80
90
70


Foxtail, Giant
10
70
0
20
50
70
50
70
80
60
40
40
50
50
20
50
90
70
80
80
90
90
50
60
90
40


Morningglory
0
50
0
0
0
70
20
70
60
50
—
0
10
20
—
40
40
—
30
80
50
60
30
90
90
80


Pigweed
60
100
0
40
90
50
50
50
80
100
90
90
100
100
50
40
90
100
100
100
100
90
70
100
70
80


Velvetleaf
50
70
0
100
100
60
50
80
100
80
100
70
50
50
40
60
100
100
100
100
100
100
50
100
100
80


Wheat
0
0
0
0
0
0
0
20
40
0
20
0
0
0
0
0
60
20
20
50
50
0
0
0
0
0












500 g ai/ha



Compounds


































189
190
191
192
193
194
195
196
197
198
199
200
202
203
204
205
206
207
208
209
210
211
212
213
214
215





Barnyardgrass
90
100
80
30
90
40
10
50
40
50
90
0
100
70
80
10
20
50
80
50
70
70
90
30
60
20


Corn
0
0
30
40
0
0
0
20
30
20
30
0
40
20
20
0
0
0
20
20
0
0
0
0
0
0


Crabgrass, Large
80
90
100
40
100
40
50
70
60
90
100
0
100
70
100
90
60
100
100
70
50
90
40
50
90
60


Foxtail, Giant
60
90
90
40
90
—
30
80
50
70
90
0
100
90
90
80
60
80
70
60
90
50
50
30
70
30


Morningglory
80
70
70
0
90
20
0
40
60
30
80
—
100
70
80
60
0
70
70
30
50
10
80
60
80
70


Pigweed
100
100
100
50
100
100
10
30
100
100
100
20
100
100
100
90
80
100
100
70
100
60
90
90
90
90


Velvetleaf
100
100
100
60
100
70
50
50
90
80
100
60
100
80
90
80
60
100
90
100
60
60
70
60
100
70


Wheat
0
0
20
20
50
0
20
20
20
20
20
0
40
30
40
0
0
0
20
0
0
0
0
0
30
0












500 g ai/ha



Compounds


































216
218
219
220
221
222
223
224
225
226
227
228
229
230
231
232
233
234
235
236
237
238
239
240
241
242





Barnyardgrass
20
100
100
90
0
60
70
90
90
100
100
100
70
80
60
50
100
80
100
90
90
100
80
—
90
0


Corn
20
0
0
10
0
0
0
20
20
0
10
50
0
0
20
0
0
20
70
10
50
50
0
40
20
0


Crabgrass, Large
80
80
100
90
10
20
80
100
100
100
100
100
100
90
90
40
100
90
100
100
100
100
100
100
90
10


Foxtail, Giant
60
50
80
40
10
60
90
70
80
90
80
90
60
50
60
70
80
60
90
70
90
90
70
80
70
0


Morningglory
30
80
80
70
0
40
—
30
80
80
80
80
80
20
80
40
90
10
90
80
80
90
50
0
30
0


Pigweed
50
90
100
100
60
0
90
100
100
100
100
100
100
80
80
90
100
60
90
90
100
100
100
100
50
0


Velvetleaf
30
90
90
100
30
60
60
80
100
100
100
100
100
80
60
60
80
90
100
100
100
100
100
80
60
0


Wheat
0
0
20
0
0
0
0
30
30
10
10
0
0
0
0
30
40
20
40
30
30
40
30
40
40
0













500 g ai/ha
125 g ai/ha



Compounds
Compounds






































243
244
245
246
247
248
249
250
251
252
253
254
255
256
1
2
3
4
7
8
9
10
11
12
13
14
15
16
17
18





Barnyardgrass
100
100
100
100
0
30
40
40
20
0
20
10
100
70
0
10
30
10
0
10
0
30
0
10
10
10
10
0
0
10


Corn
60
40
20
50
0
20
0
0
0
0
—
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Crabgrass, Large
100
100
100
100
0
70
80
90
80
20
80
50
90
80
10
80
50
20
0
40
90
90
20
50
60
30
40
40
20
60


Foxtail, Giant
100
100
90
90
0
20
40
60
40
10
70
30
50
30
0
50
0
10
0
40
40
70
10
20
50
40
40
30
0
40


Morningglory
90
80
60
60
0
40
70
60
40
10
70
—
60
50
—
60
0
0
0
0
20
10
0
30
0
10
0
0
0
20


Pigweed
100
100
90
100
0
40
100
100
60
40
80
0
90
90
20
100
80
90
10
90
50
100
60
80
40
100
30
30
80
70


Velvetleaf
100
100
100
100
0
60
90
90
70
50
90
20
100
80
60
60
80
40
60
50
70
90
60
70
80
90
40
0
40
30


Wheat
70
40
20
50
0
20
0
10
0
0
20
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0












125 g ai/ha



Compounds














































19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56





Barnyardgrass
10
0
0
10
0
10
20
0
10
10
0
0
0
0
10
10
0
10
0
10
10
10
0
0
10
30
40
0
10
20
20
50
10
40
40
0
0
50


Corn
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Crabgrass, Large
20
0
0
40
10
30
60
20
30
20
20
0
0
20
80
90
10
10
10
30
60
60
20
40
50
80
50
30
70
90
60
90
30
90
90
0
0
80


Foxtail, Giant
10
0
0
20
0
40
50
30
30
0
30
0
0
10
30
60
0
10
10
10
50
50
10
10
10
30
0
0
50
70
20
50
30
80
70
0
0
70


Morningglory
0
0
0
20
0
20
0
10
20
20
40
0
0
0
0
10
—
0
0
0
40
10
0
0
0
20
20
10
60
40
30
40
—
30
80
0
30
50


Pigweed
80
0
—
70
50
90
50
60
70
80
50
0
40
30
80
90
10
0
50
50
60
70
90
90
90
60
80
60
80
90
80
90
90
100
90
80
50
90


Velvetleaf
50
0
0
30
40
90
80
20
60
20
20
20
10
20
50
50
0
60
50
70
70
70
30
70
60
70
60
40
70
80
80
80
70
100
80
60
60
80


Wheat
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0












125 g ai/ha



Compounds










































57
58
59
60
61
62
63
64
65
66
67
68
69
70
71
72
73
74
75
76
77
78
79
80
81
82
83
84
85
86
87
88
89
90





Barnyardgrass
40
30
40
60
30
10
10
10
0
20
0
0
10
0
0
10
0
30
40
0
20
0
0
0
50
0
30
0
50
20
20
10
20
40


Corn
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
—
0
0
0
0


Crabgrass, Large
90
70
90
90
60
60
90
80
10
90
30
70
90
40
10
70
70
70
90
50
50
10
50
50
90
—
70
0
100
—
—
—
60
60


Foxtail, Giant
70
50
50
60
10
60
50
50
0
—
—
—
40
30
0
0
50
0
50
0
0
0
0
10
30
10
40
0
—
—
—
—
20
30


Morningglory
20
—
—
—
60
90
10
0
0
0
30
20
0
0
0
—
10
40
60
0
—
0
0
0
0
0
20
0
50
0
50
50
0
0


Pigweed
90
70
90
90
80
80
100
80
0
90
90
90
100
60
—
50
100
90
100
50
80
50
100
60
100
90
80
90
—
—
—
—
90
80


Velvetleaf
80
70
100
80
60
70
80
60
30
70
70
70
70
70
50
90
80
70
90
20
70
20
70
50
100
50
70
0
70
—
100
80
70
70


Wheat
0
0
0
0
0
0
—
0
0
0
0
0
0
0
0
0
10
0
0
0
0
0
0
0
0
0
0
0
0
—
10
0
0
0












125 g ai/ha



Compounds



































91
92
93
94
95
96
97
98
99
100
101
102
103
104
105
106
107
108
109
110
111
112
113
114
115
116
117





Barnyardgrass
60
60
80
0
40
90
60
0
10
40
20
40
0
0
0
10
40
30
10
20
30
0
10
30
0
10
50


Corn
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
20
0
0
0
0
0
0
0
0
0
0


Crabgrass, Large
90
90
90
30
50
100
100
90
60
80
70
80
40
0
30
70
90
70
40
40
90
60
70
90
20
30
60


Foxtail, Giant
40
70
60
0
30
50
60
40
40
50
30
80
0
0
30
40
60
30
0
0
—
20
70
40
20
10
20


Morningglory
20
0
80
10
70
80
70
70
—
70
80
80
20
0
0
50
70
80
40
40
50
0
30
0
60
0
40


Pigweed
90
100
100
70
90
100
100
100
90
80
70
60
90
80
80
80
100
90
90
80
100
20
100
100
70
60
90


Velvetleaf
100
90
90
40
90
100
100
90
80
60
80
80
60
0
0
40
100
80
70
60
90
40
100
70
60
30
70


Wheat
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0












125 g ai/ha



Compounds


































118
119
120
121
122
123
124
125
126
127
128
129
130
131
132
133
134
135
136
138
139
140
141
142
143
144





Barnyardgrass
30
70
70
20
30
50
20
10
70
40
10
30
20
50
10
10
0
0
0
20
40
60
60
10
40
0


Corn
0
20
20
0
0
0
0
0
0
0
0
0
20
0
0
0
0
0
0
0
0
0
0
0
0
0


Crabgrass, Large
60
100
100
90
90
100
60
80
90
90
80
70
40
80
50
50
0
0
20
40
90
70
80
30
50
10


Foxtail, Giant
10
90
90
80
30
50
10
40
60
50
60
40
20
60
20
40
0
0
0
30
20
40
40
0
10
0


Morningglory
10
60
30
0
40
70
60
0
70
10
80
—
10
—
0
0
—
20
30
0
0
30
0
0
10
0


Pigweed
90
100
100
80
100
90
100
90
100
100
80
100
90
100
10
40
0
40
80
50
70
80
70
90
70
0


Velvetleaf
70
90
80
80
100
70
70
60
80
70
80
80
80
80
50
50
70
40
70
20
60
80
70
20
70
20


Wheat
0
20
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0












125 g ai/ha



Compounds


































145
146
147
148
149
150
151
152
153
154
155
156
157
158
159
160
161
162
163
164
165
166
167
168
169
170





Barnyardgrass
20
60
70
10
20
0
20
50
40
0
10
0
0
20
30
40
10
10
0
10
0
0
0
0
0
0


Corn
0
0
0
0
0
0
0
0
20
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Crabgrass, Large
50
60
100
0
30
0
10
90
80
10
60
10
20
70
80
80
50
90
0
30
0
10
20
30
40
10


Foxtail, Giant
30
30
70
0
10
0
20
60
20
10
30
10
10
10
60
20
50
30
0
40
0
0
10
10
40
10


Morningglory
0
10
40
0
0
0
—
60
20
0
0
0
0
0
0
70
0
0
0
10
—
0
0
0
0
0


Pigweed
70
70
90
0
80
0
50
100
100
30
90
70
0
100
100
80
90
100
0
60
0
0
10
10
0
30


Velvetleaf
90
70
80
30
40
0
50
60
100
40
60
0
60
50
70
60
70
60
10
40
0
40
70
0
20
10


Wheat
0
0
0
0
0
0
0
20
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0












125 g ai/ha



Compounds


































171
172
173
174
175
176
177
178
179
180
181
182
183
184
185
186
187
188
189
190
191
192
193
194
195
196





Barnyardgrass
20
10
0
0
0
10
0
0
0
30
20
70
20
20
0
0
20
0
20
10
10
10
80
0
0
0


Corn
0
0
0
10
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
40
0
0
0
0


Crabgrass, Large
70
10
40
20
30
0
0
10
20
80
90
100
90
30
0
30
30
30
30
60
50
10
90
20
0
0


Foxtail, Giant
30
10
20
0
0
10
0
10
10
30
30
50
60
30
0
20
30
10
30
60
40
0
90
—
0
0


Morningglory
0
0
0
0
0
0
0
0
0
0
0
70
20
10
—
20
80
70
—
—
0
0
80
—
0
0


Pigweed
50
10
50
30
60
60
0
0
50
90
100
90
90
70
0
50
60
60
70
70
80
0
100
50
0
0


Velvetleaf
80
50
70
20
40
10
10
0
50
80
70
70
100
80
0
60
70
70
70
70
60
0
100
30
0
0


Wheat
20
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0












125 g ai/ha



Compounds


































197
198
199
200
202
203
204
205
206
207
208
209
210
211
212
213
214
215
216
218
219
220
221
222
223
224





Barnyardgrass
0
0
20
0
20
30
30
0
0
10
10
0
10
10
10
0
10
0
0
20
40
10
0
0
0
0


Corn
0
0
20
0
20
0
20
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
20


Crabgrass, Large
0
10
60
0
50
20
40
20
10
60
80
20
10
10
0
0
30
0
0
10
50
20
0
20
30
70


Foxtail, Giant
0
70
60
0
50
30
20
10
0
30
40
10
20
20
10
10
30
10
0
0
10
0
0
30
30
20


Morningglory
0
0
70
0
0
0
0
0
0
0
0
0
0
0
0
—
0
0
0
0
20
0
0
0
10
—


Pigweed
20
10
80
0
90
100
100
10
30
80
60
0
60
40
60
50
70
20
0
20
90
80
0
0
60
70


Velvetleaf
40
0
90
0
70
50
50
10
0
70
60
60
40
30
50
40
90
0
0
50
30
40
20
0
0
50


Wheat
0
0
0
0
0
0
20
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0












125 g ai/ha



Compounds


































225
226
227
228
229
230
231
232
233
234
235
236
237
238
239
240
241
242
243
244
245
246
247
248
249
250





Barnyardgrass
20
30
50
40
0
10
0
0
30
0
90
50
20
70
20
40
10
0
70
30
40
10
0
0
0
0


Corn
0
0
0
0
0
0
0
0
0
0
20
0
0
0
0
0
0
0
30
20
0
0
0
0
0
0


Crabgrass, Large
60
90
90
100
80
30
40
10
40
60
100
80
40
90
70
50
20
0
100
90
80
100
0
10
40
30


Foxtail, Giant
40
70
40
50
50
40
0
0
20
10
70
40
40
50
20
40
10
0
90
70
80
90
0
10
20
30


Morningglory
30
60
50
70
40
0
10
0
50
—
80
70
10
40
—
0
0
0
70
30
20
20
0
0
30
10


Pigweed
90
100
80
100
90
—
50
0
70
50
90
80
30
100
70
20
20
0
100
100
80
100
0
0
80
60


Velvetleaf
80
80
90
100
100
60
50
0
60
30
100
80
80
90
80
60
20
0
90
50
70
90
0
20
60
50


Wheat
0
0
0
0
0
0
0
0
0
0
10
0
0
0
0
0
0
0
30
0
0
0
0
0
0
0















125 g ai/ha





Compounds
















251
252
253
254
255
256







Barnyardgrass
0
0
10
0
10
0



Corn
0
0
0
0
0
0



Crabgrass, Large
20
10
30
0
20
10



Foxtail, Giant
10
0
20
0
0
0



Morningglory
0
0
40
0
40
0



Pigweed
0
0
20
0
70
0



Velvetleaf
50
20
50
0
60
20



Wheat
0
0
0
0
0
0










Test B


Seeds of plant species selected from blackgrass (Alopecurus myosuroides), downy bromegrass (Bromus tectorum), green foxtail (Setaria viridis), Italian ryegrass (Lolium multiflorum), wheat (Triticum aestivum), wild oat (Avena fatua), deadnettle (henbit deadnettle, Lamium amplexicaule), galium (catchweed bedstraw, Galium aparine), bermudagrass (Cynodon dactylon), Surinam grass (Brachiaria decumbens), cocklebur (Xanthium strumarium), corn (Zea mays), large crabgrass (Digitaria sanguinalis), woolly cupgrass (Eriochloa villosa), giant foxtail (Setaria faberii), goosegrass (Eleusine indica), johnsongrass (Sorghum halepense), kochia (Kochia scoparia), lambsquarters (Chenopodium album), morningglory (Ipomoea coccinea), nightshade (eastern black nightshade, Solanum ptycanthum), yellow nutsedge (Cyperus esculentus), pigweed (Amaranthus retroflexus), ragweed (common ragweed, Ambrosia elatior), Russian thistle (Salsola kali), soybean (Glycine max), sunflower (common oilseed sunflower, Helianthus annuus) and velvetleaf (Abutilon theophrasti) were planted into a blend of loam soil and sand and treated preemergence with test compounds 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 winter barley (Hordeum vulgare), canarygrass (Phalaris minor), chickweed (Stellaria media) and windgrass (Apera spica-venti) were planted in pots containing Redi-Earth® planting medium (Scotts Company, 14111 Scottslawn Road, Marysville, Ohio 43041) comprising spaghnum peat moss, vermiculite, wetting agent and starter nutrients and treated with postemergence applications of some of the test chemicals formulated in the same manner. Plants ranged in height from 2 to 18 cm (1- to 4-leaf stage) for postemergence treatments.


Plant species in the flooded paddy test consisted of rice (Oryza sativa), umbrella sedge (Cyperus difformis), ducksalad (Heteranthera limosa) and barnyardgrass (Echinochloa crus-galli) grown to the 2-leaf stage for testing. At the time of treatment, test pots were flooded with water 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 days, after which time all treated plants were visually evaluated and compared to controls. 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







Flood









250 g ai/ha



Compounds
















































1
2
3
4
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42





Barnyardgrass
0
0
0
20
0
45
50
0
25
0
35
0
35
10
25
50
15
0
0
0
0
20
0
0
40
20
30
0
0
40
40
0
0
15
0
0
30
40
30
0


Ducksalad
0
78
70
85
0
90
75
80
80
55
95
40
60
75
45
90
90
75
75
60
45
75
0
85
85
85
85
50
75
95
95
65
0
40
60
65
90
90
75
50


Rice
0
8
0
0
0
50
0
0
25
0
25
0
0
10
15
25
0
15
0
0
15
0
0
0
0
0
0
0
0
30
50
0
—
35
20
0
15
25
0
20


Sedge, Umbrella
0
75
60
90
0
95
75
55
85
65
85
40
30
50
80
85
95
60
65
65
45
75
0
85
85
80
80
50
75
90
85
40
0
20
40
40
90
85
80
30












250 g ai/ha



Compounds















































43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
61
62
63
64
65
66
67
68
69
70
71
72
73
74
75
76
77
78
79
80
81





Barnyardgrass
20
30
30
0
20
35
0
60
55
55
75
0
20
35
25
0
45
40
20
0
10
0
0
45
0
20
30
20
0
30
0
40
60
0
65
0
30
30
60


Ducksalad
80
90
90
20
95
85
70
85
95
70
75
40
50
50
60
0
40
60
0
30
40
60
0
20
0
40
20
0
0
0
0
0
50
0
40
20
40
30
40


Rice
40
40
20
10
25
65
15
20
60
60
85
0
25
20
25
0
15
15
0
0
10
0
0
20
0
30
0
20
0
20
0
0
45
0
15
20
20
15
15


Sedge, Umbrella
80
90
85
65
85
75
85
95
90
40
90
40
60
75
75
0
75
85
0
0
0
40
0
50
0
0
40
20
25
30
0
60
50
0
40
40
30
40
40












250 g ai/ha



Compounds







































82
83
84
85
86
87
88
89
90
91
92
93
94
95
96
97
98
99
100
101
102
103
104
105
106
107
108
109
110
111
112





Barnyardgrass
20
40
0
65
60
60
60
40
30
65
45
85
60
70
85
75
50
55
75
40
70
0
0
0
15
60
30
20
40
60
40


Ducksalad
20
50
20
65
65
20
80
100
90
100
85
80
30
20
75
70
0
80
85
30
85
0
0
0
0
40
70
100
75
75
95


Rice
20
30
0
20
40
70
50
15
0
15
40
45
35
30
15
40
40
60
—
20
35
0
0
0
20
45
10
25
30
30
15


Sedge, Umbrella
50
50
50
80
85
70
65
85
80
100
85
90
85
75
90
80
75
85
85
65
75
0
0
0
0
85
95
80
75
85
90












250 g ai/ha



Compounds


































113
114
115
116
117
118
119
120
121
122
123
124
125
126
127
128
129
130
131
132
133
134
135
136
138
139





Barnyardgrass
15
40
65
75
75
70
50
65
70
40
70
30
60
75
75
40
60
85
50
30
0
0
0
25
25
35


Ducksalad
70
75
85
85
100
100
70
85
80
0
95
0
70
85
80
100
100
100
85
100
100
0
40
75
80
90


Rice
0
20
20
0
15
15
35
40
55
15
40
20
0
15
35
35
30
25
55
0
0
0
0
20
15
30


Sedge, Umbrella
70
40
90
90
95
85
75
75
70
45
85
40
90
85
80
75
60
100
85
100
100
0
0
50
80
85












250 g ai/ha



Compounds


































140
141
142
143
144
145
146
147
148
151
152
153
154
155
156
158
161
162
164
178
179
183
184
185
186
187





Barnyardgrass
45
50
10
20
20
25
30
75
50
55
75
45
40
45
60
60
30
55
0
80
30
35
25
0
30
80


Ducksalad
85
85
80
90
100
80
100
100
100
100
100
100
100
95
100
100
80
100
85
100
100
95
100
75
100
100


Rice
40
35
0
0
25
0
35
15
50
50
60
65
75
45
35
85
50
90
35
70
65
0
15
0
65
70


Sedge, Umbrella
85
85
80
65
100
80
90
80
95
100
100
95
100
100
100
100
60
100
90
95
95
90
95
60
90
100












250 g ai/ha



Compounds


































188
189
190
191
192
193
194
195
196
197
198
199
200
203
204
206
207
208
209
210
211
212
213
214
215
216





Barnyardgrass
0
70
30
25
0
50
15
20
30
30
35
25
38
20
60
0
20
25
20
40
35
50
30
20
40
0


Ducksalad
85
100
100
100
75
100
80
85
95
85
95
90
85
95
100
90
50
75
85
90
85
95
100
95
85
95


Rice
15
60
15
0
20
65
0
15
65
45
50
0
23
0
60
20
15
0
20
25
15
10
20
15
15
0


Sedge, Umbrella
85
100
95
85
60
90
65
65
80
85
80
85
70
85
95
85
70
70
80
80
80
95
90
85
90
100












250 g ai/ha



Compounds


































217
218
219
220
221
222
223
224
226
227
228
229
230
231
232
233
234
235
236
237
238
239
243
244
245
246





Barnyardgrass
0
40
60
40
20
0
0
30
95
60
80
30
40
40
50
65
0
75
20
30
40
15
85
75
65
60


Ducksalad
40
95
90
100
70
65
0
75
40
80
80
40
0
0
85
100
70
100
70
100
100
80
100
100
100
100


Rice
20
15
75
70
15
0
0
60
65
55
60
20
45
0
0
50
0
55
0
45
0
0
75
85
90
65


Sedge, Umbrella
40
85
85
85
75
40
0
75
60
85
85
70
75
75
80
85
40
80
40
100
80
75
100
100
100
100













250 g ai/ha
125 g ai/ha



Compounds
Compounds










































248
249
250
251
252
253
254
255
256
1
2
3
4
7
8
9
10
11
12
13
14
16
17
18
19
20
21
22
23
33
34
35
36
37





Barnyardgrass
40
0
10
20
0
20
15
0
0
0
0
0
0
0
20
0
0
0
0
0
0
0
25
20
0
0
0
0
0
30
0
0
0
0


Ducksalad
90
90
75
80
0
90
100
80
85
0
58
70
75
0
85
60
75
65
35
0
30
75
30
65
85
65
70
30
45
80
30
0
0
50


Rice
0
15
0
10
0
20
0
0
0
0
0
0
0
0
15
0
0
20
0
0
0
0
0
25
0
0
0
0
0
20
0
0
20
0


Sedge, Umbrella
85
90
70
75
0
85
80
60
75
0
45
60
80
0
85
70
55
40
50
60
0
40
70
50
85
50
60
40
40
50
0
0
0
30












125 g ai/ha



Compounds














































38
49
50
51
52
53
54
55
56
57
58
59
60
61
62
63
64
65
66
67
68
69
70
71
72
76
79
80
81
82
83
84
85
86
87
88
89
90





Barnyardgrass
0
0
35
40
40
55
0
20
20
20
0
20
30
0
0
0
0
0
0
0
0
20
0
0
0
0
20
25
40
15
15
0
55
50
55
40
30
15


Ducksalad
60
40
85
85
40
75
30
0
40
40
0
0
40
0
0
40
50
0
0
0
30
0
0
0
0
0
15
30
15
0
40
0
60
55
20
75
100
80


Rice
0
10
15
25
50
60
0
15
15
15
0
15
0
0
0
0
0
0
0
0
20
0
0
0
20
0
15
0
15
15
0
0
15
20
60
40
0
0


Sedge, Umbrella
30
0
85
85
30
90
0
40
60
50
0
50
75
0
0
0
0
0
30
0
0
0
20
0
0
0
0
30
30
40
40
30
80
70
50
40
85
75












125 g ai/ha



Compounds





































91
92
93
94
95
96
97
98
99
100
101
102
103
104
105
106
108
109
110
111
123
124
125
126
127
128
129
130
132





Barnyardgrass
60
20
75
40
65
80
60
30
20
60
40
60
0
0
0
0
15
20
20
50
55
0
40
60
65
15
10
0
0


Ducksalad
90
70
80
25
0
50
30
0
75
85
30
80
0
0
0
0
60
65
75
75
90
0
60
85
60
95
90
80
80


Rice
15
25
20
20
30
15
0
0
0
35
0
20
0
0
0
20
0
20
30
0
30
20
0
0
25
10
0
0
0


Sedge, Umbrella
100
70
80
85
50
85
70
75
65
80
30
65
0
0
0
0
60
75
50
80
75
20
90
80
60
60
60
75
60












125 g ai/ha



Compounds


































133
142
143
144
145
146
147
148
151
152
153
154
155
156
157
158
161
162
163
164
166
167
168
170
171
172





Barnyardgrass
0
0
0
0
0
0
45
15
30
50
35
0
20
40
0
20
0
40
0
0
20
20
0
30
20
20


Ducksalad
100
80
80
75
80
80
80
90
100
100
100
70
85
80
70
100
0
100
60
0
60
70
30
45
70
60


Rice
0
0
0
20
0
0
10
20
15
30
55
60
25
20
0
40
45
90
20
20
0
0
0
20
0
0


Sedge, Umbrella
95
65
0
95
60
80
40
85
100
85
80
95
85
100
75
100
0
100
70
0
70
60
20
35
80
75












125 g ai/ha



Compounds


































173
174
175
176
177
178
179
180
181
182
183
184
185
186
190
191
192
193
194
195
196
197
198
199
200
203





Barnyardgrass
15
0
20
0
15
60
20
15
70
0
0
20
0
30
20
0
0
45
10
0
20
20
30
15
23
0


Ducksalad
75
95
95
75
70
100
95
75
90
85
80
100
75
90
40
75
75
85
50
70
95
80
85
85
85
95


Rice
15
0
0
20
20
70
25
30
65
0
0
15
0
45
15
0
0
30
0
0
40
30
20
0
10
0


Sedge, Umbrella
85
95
85
85
75
95
85
65
85
75
65
80
65
80
30
80
50
70
0
50
75
75
80
75
43
75












125 g ai/ha



Compounds


































204
207
208
209
210
211
212
213
215
216
218
219
220
221
223
224
226
227
228
229
230
235
236
237
238
239





Barnyardgrass
25
0
15
0
20
25
0
0
30
0
30
20
30
0
0
0
95
50
75
0
20
50
0
0
30
0


Ducksalad
90
0
40
85
90
85
90
90
85
90
85
65
85
70
0
0
30
75
75
0
0
100
60
90
80
70


Rice
0
15
0
10
20
0
0
0
0
0
10
70
50
0
0
0
60
45
35
0
30
45
0
0
0
0


Sedge, Umbrella
90
60
40
70
75
70
90
85
75
80
85
60
20
75
0
0
50
85
75
50
40
80
0
55
65
40













125 g ai/ha
62 g ai/ha



Compounds
Compounds









































243
244
245
246
248
249
250
251
253
254
255
256
1
2
3
4
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23





Barnyardgrass
75
40
40
20
0
0
10
0
0
10
0
0
0
0
0
0
0
0
0
0
0
0
0
0
20
0
20
20
0
0
0
0
0


Ducksalad
100
100
100
100
80
80
70
50
85
85
60
80
0
40
0
40
0
85
30
20
0
25
0
20
0
40
30
50
75
60
70
20
35


Rice
95
60
50
65
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
10
0
0
0
0
0
0
15
0
0
0
0
0


Sedge, Umbrella
100
100
100
100
75
85
65
65
75
75
50
75
0
0
50
65
0
65
30
40
0
40
0
0
0
0
70
30
70
40
50
30
30












62 g ai/ha



Compounds














































24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
61





Barnyardgrass
0
0
0
0
10
0
0
0
10
20
0
0
0
0
0
0
0
0
0
20
0
0
0
0
0
0
0
20
0
40
0
20
15
0
0
0
0
0


Ducksalad
20
0
75
75
70
70
20
60
75
75
0
0
0
30
20
80
0
70
30
70
80
20
20
65
0
0
75
30
0
65
0
0
20
0
0
0
0
0


Rice
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
20
15
10
15
0
0
10
15
0
20
0
10
0
0
0
15
0
0


Sedge, Umbrella
0
0
75
75
70
70
20
60
75
30
0
0
0
20
0
90
70
70
30
30
80
70
45
70
40
0
75
40
30
85
0
30
40
0
0
40
30
0












62 g ai/ha



Compounds















































62
63
64
65
66
67
68
69
70
71
72
73
74
75
76
77
78
79
80
81
82
83
84
85
86
87
88
89
90
91
92
93
94
95
96
97
98
99
100





Barnyardgrass
0
0
0
0
0
0
0
0
0
0
0
0
0
20
0
30
0
0
20
0
0
0
0
25
40
45
20
20
0
20
0
60
0
35
65
40
30
20
45


Ducksalad
0
20
30
0
0
0
0
0
0
0
0
0
0
30
0
30
0
0
20
0
0
30
0
50
55
30
40
90
65
90
30
55
20
0
0
30
0
40
75


Rice
0
0
0
0
0
0
15
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
20
0
0
0
15
0
15
0
20
15
0
0
0
30


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0
0
0
30
0
0
40
30
0
20
0
0
30
0
75
30
20
30
85
60
95
65
75
70
20
75
40
65
50
75












62 g ai/ha



Compounds


































101
102
103
104
105
106
107
108
109
110
111
112
113
114
115
116
117
118
119
120
121
122
123
124
125
126





Barnyardgrass
40
60
0
0
0
0
40
0
0
0
40
35
10
20
50
65
65
50
30
20
30
20
40
0
25
45


Ducksalad
30
40
0
0
0
0
0
50
60
40
30
85
25
65
85
80
—
100
30
30
45
0
80
0
40
80


Rice
0
15
0
0
0
0
20
0
0
0
0
0
0
0
20
0
0
0
20
0
0
0
20
15
0
0


Sedge, Umbrella
20
40
0
0
0
0
60
40
60
35
75
85
40
30
70
75
95
70
25
40
30
20
70
0
35
70












62 g ai/ha



Compounds


































127
128
129
130
131
132
133
134
135
136
138
139
140
141
142
143
144
145
146
147
148
151
152
153
154
155





Barnyardgrass
40
10
0
0
20
0
0
0
0
20
0
10
20
20
0
0
0
0
0
10
0
15
25
0
0
0


Ducksalad
30
95
90
80
40
50
60
0
30
55
70
75
50
75
0
80
60
80
60
60
90
80
90
65
50
60


Rice
15
0
0
0
25
0
0
0
0
15
0
10
0
0
0
0
20
0
0
0
10
0
20
35
0
0


Sedge, Umbrella
20
30
0
60
20
0
60
0
0
45
70
70
75
80
0
0
65
0
50
40
80
85
0
0
95
60












62 g ai/ha



Compounds


































156
158
161
162
164
178
179
183
184
185
186
187
188
189
190
191
192
193
194
195
196
197
198
199
200
203





Barnyardgrass
20
20
0
25
0
20
10
0
0
0
20
45
0
30
0
0
0
20
0
0
0
0
0
0
0
0


Ducksalad
65
75
0
100
0
75
90
65
100
70
90
95
70
100
20
85
60
50
50
50
60
65
50
85
83
75


Rice
30
30
50
25
0
20
0
0
15
0
20
15
0
20
15
0
0
15
0
0
0
0
20
0
0
0


Sedge, Umbrella
95
85
0
100
0
85
80
50
80
75
80
95
80
95
0
75
40
30
0
0
30
70
20
70
33
65












62 g ai/ha



Compounds


































204
206
207
208
209
210
211
212
213
214
215
216
217
218
219
220
221
222
223
224
226
227
228
229
230
231





Barnyardgrass
15
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
60
40
40
0
0
40


Ducksalad
70
70
0
30
50
85
—
85
85
0
75
90
0
80
20
40
65
50
0
0
0
—
50
0
0
0


Rice
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
15
0
0
0
0
40
30
20
0
20
0


Sedge, Umbrella
75
60
40
40
50
75
0
85
80
0
0
65
40
80
40
0
60
30
0
0
40
85
75
0
30
0













62 g ai/ha
31 g ai/ha



Compounds
Compounds




































232
233
234
235
236
237
238
239
243
244
245
246
248
249
250
251
252
253
254
255
256
1
2
3
4
7
8
9





Barnyardgrass
30
20
0
20
0
0
0
0
30
20
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Ducksalad
85
100
20
95
0
65
40
0
85
80
100
100
80
65
30
0
0
75
85
50
40
0
15
0
20
0
30
0


Rice
0
25
0
0
0
0
0
0
60
0
50
30
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Sedge, Umbrella
80
70
0
70
0
45
0
0
90
0
100
85
65
60
65
50
0
65
50
20
40
0
0
40
50
0
30
0












31 g ai/ha



Compounds















































10
11
12
13
14
16
17
18
19
20
21
22
23
33
34
35
36
37
38
49
50
51
52
53
54
55
56
57
58
59
60
61
62
63
64
65
66
67
68





Barnyardgrass
0
0
0
0
0
0
0
10
0
0
0
0
0
0
0
0
0
0
0
0
0
15
0
20
0
0
10
0
0
0
0
0
0
0
0
0
0
0
0


Ducksalad
0
0
0
0
0
0
0
20
0
60
60
0
20
60
0
0
0
0
0
0
70
0
0
40
0
0
0
0
0
0
0
0
0
0
30
0
0
0
0


Rice
0
0
0
0
0
0
0
10
0
0
0
0
0
0
0
0
0
0
0
0
0
10
0
15
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Sedge, Umbrella
0
0
20
0
0
0
0
0
0
0
40
0
20
20
0
0
0
0
0
0
75
30
20
40
0
0
30
0
0
30
0
0
0
0
0
0
0
0
0












31 g ai/ha



Compounds











































69
70
71
72
76
79
80
81
82
83
84
85
86
87
88
89
90
91
92
93
94
95
96
97
98
99
100
101
102
103
104
105
106
108
109





Barnyardgrass
0
0
0
0
0
0
15
0
0
0
0
25
30
20
0
20
0
15
0
30
0
20
60
30
0
0
20
20
15
0
0
0
0
0
0


Ducksalad
0
0
0
0
0
0
0
0
0
20
0
40
0
20
30
45
50
65
20
40
0
0
0
30
0
30
35
20
30
0
0
0
0
40
50


Rice
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
10
0
0
0
0
0
10
0
0
0
0
0
0


Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0
0
50
20
0
0
30
50
75
65
70
20
0
50
30
40
50
40
0
30
0
0
0
0
0
50












31 g ai/ha



Compounds


































110
111
123
124
125
126
127
128
129
130
132
133
142
143
144
145
146
147
148
151
152
153
154
155
156
157





Barnyardgrass
0
0
30
0
0
20
0
0
0
0
0
0
0
0
0
0
0
0
0
0
15
0
0
0
0
0


Ducksalad
0
30
30
0
20
75
0
90
0
60
0
60
0
80
50
80
0
60
90
80
0
0
0
0
0
50


Rice
0
0
0
0
0
0
0
0
0
0
0
0
0
0
15
0
0
0
20
20
20
35
0
0
30
0


Sedge, Umbrella
30
0
40
0
25
50
0
0
0
40
0
0
0
0
50
0
0
0
80
85
0
0
0
60
0
40












31 g ai/ha



Compounds


































158
161
162
163
164
166
167
168
170
171
172
173
174
175
176
177
178
179
180
181
182
183
184
185
186
190





Barnyardgrass
20
0
20
0
0
0
0
0
0
0
0
0
0
0
0
0
20
0
0
0
0
0
0
0
0
0


Ducksalad
50
0
98
30
0
0
0
0
0
40
20
30
80
75
40
30
75
90
60
85
60
30
95
75
90
20


Rice
20
25
0
10
0
0
0
0
15
0
0
0
0
0
15
15
0
0
15
0
0
0
15
0
10
15


Sedge, Umbrella
70
0
95
70
0
50
20
0
0
70
0
0
85
75
70
60
55
40
20
75
50
0
65
65
70
0












31 g ai/ha



Compounds


































191
192
193
194
195
196
197
198
199
200
203
204
207
208
209
210
211
212
213
215
216
218
219
220
221
223





Barnyardgrass
0
0
0
0
0
0
0
0
0
0
0
10
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Ducksalad
65
60
40
40
0
40
65
40
85
38
40
50
0
0
0
75
50
85
75
70
50
75
0
30
20
0


Rice
0
0
0
0
0
0
0
15
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Sedge, Umbrella
60
0
0
0
0
20
65
20
60
30
0
70
0
0
0
50
0
80
65
0
0
75
20
0
0
0












31 g ai/ha



Compounds































224
226
227
228
229
230
235
236
237
238
239
243
244
245
246
248
249
250
251
253
254
255
256





Barnyardgrass
0
50
20
15
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Ducksalad
0
0
—
40
0
0
95
0
0
0
0
0
35
100
85
75
0
30
0
60
45
0
30


Rice
0
20
20
0
0
0
0
0
0
0
0
45
0
50
0
0
0
0
0
0
0
0
0


Sedge, Umbrella
0
30
80
65
0
0
0
0
0
0
0
0
0
60
0
50
0
0
0
60
30
0
30










Postemergence









250 g ai/ha



Compounds


































1
3
4
7
8
9
10
11
12
14
24
26
27
29
33
34
36
37
38
39
40
42
44
45
46
47





Barley
0
0
10
0
20
35
5
10
0
40
70
0
20
0
0
30
—
0
35
10
10
5
15
5
0
35


Bermudagrass
65
80
100
70
100
98
95
100
100
80
100
75
100
100
98
98
100
100
100
100
100
98
98
100
90
—


Blackgrass
5
5
50
5
20
70
50
40
20
5
50
40
50
50
30
40
15
30
40
20
15
20
30
25
10
30


Bromegrass, Downy
10
45
55
5
10
50
20
45
20
70
75
40
30
45
20
50
65
45
85
0
85
25
85
50
25
55


Canarygrass
0
5
80
0
85
60
40
90
40
50
60
60
50
40
5
50
50
30
45
20
35
0
40
30
0
40


Chickweed
90
100
100
100
100
98
98
100
100
80
100
85
80
85
100
100
100
100
100
100
100
95
100
100
98
100


Cocklebur
85
100
100
70
100
45
98
100
100
98
100
100
98
98
95
95
—
—
—
98
—
95
98
95
90
100


Corn
0
15
85
10
80
80
65
85
75
70
85
50
70
60
15
50
85
75
90
65
90
45
85
80
75
—


Crabgrass, Large
65
90
100
60
100
95
80
100
90
85
100
80
60
80
98
98
98
90
100
90
100
90
98
85
75
100


Cupgrass, Woolly
20
55
100
65
100
85
75
95
80
80
95
85
80
85
90
95
98
100
100
90
98
55
95
80
45
100


Deadnettle
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Foxtail, Giant
50
65
100
60
100
100
95
100
98
95
95
95
90
95
95
95
98
100
100
95
100
85
98
98
85
98


Foxtail, Green
40
50
60
40
95
95
70
98
70
85
95
95
90
90
90
95
90
95
95
90
95
85
90
95
85
95



Galium

—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Goosegrass
80
95
98
35
100
100
98
98
100
85
98
95
98
95
85
95
95
95
95
75
98
95
95
90
80
98


Johnsongrass
20
15
98
0
100
95
75
98
75
80
80
70
80
45
40
100
100
85
100
98
100
65
95
100
75
—



Kochia

45
95
100
50
100
85
20
98
65
—
100
—
100
—
98
100
65
65
100
95
75
100
95
98
30
100


Lambsquarters
90
100
100
75
100
95
95
98
98
85
100
98
98
98
100
100
100
100
100
100
100
100
98
100
95
100


Morningglory
65
70
95
20
100
75
55
80
95
95
90
75
90
98
85
95
75
95
100
95
85
98
80
90
80
95


Nutsedge, Yellow
45
80
80
0
85
70
75
60
80
50
70
35
55
70
80
65
60
65
55
45
—
70
55
60
75
70


Oat, Wild
10
50
50
10
35
55
40
70
20
50
80
60
65
80
55
70
85
80
85
40
90
25
85
70
30
60


Pigweed
90
100
100
98
100
100
100
98
100
98
80
98
100
85
100
98
98
100
100
100
100
100
100
100
80
100


Ragweed
75
100
100
85
100
100
98
100
100
98
98
100
100
100
98
98
95
98
95
98
98
85
98
98
80
95


Ryegrass, Italian
0
5
20
20
50
45
20
40
5
50
50
45
10
45
45
40
15
30
65
20
10
15
35
35
10
50


Soybean
80
90
100
85
100
98
98
100
100
90
100
98
100
98
100
100
100
100
100
100
100
95
95
98
90
98


Surinam Grass
20
65
90
25
80
85
80
85
85
55
80
60
80
85
90
85
95
95
95
70
100
65
95
95
90
100


Velvetleaf
90
100
100
98
100
98
85
100
100
100
98
98
90
98
100
100
100
100
100
95
100
98
100
95
90
100


Wheat
5
30
70
15
35
30
5
45
0
20
50
30
30
40
5
55
5
5
60
20
35
10
30
30
0
15


Windgrass
5
5
75
5
40
80
40
98
50
50
80
60
60
50
60
80
85
70
90
—
90
—
—
—
50
—












250 g ai/ha



Compounds


































48
49
50
51
52
53
55
56
58
59
61
62
63
64
66
67
68
70
71
72
73
74
75
77
79
80





Barley
10
0
5
50
25
70
0
—
10
10
0
30
0
35
0
30
30
90
5
0
10
0
0
0
55
75


Bermudagrass
100
98
100
98
100
98
90
100
100
100
90
90
95
98
95
85
98
98
98
85
90
98
98
95
85
55


Blackgrass
30
30
15
55
30
50
10
20
40
60
5
50
50
15
15
10
20
50
5
0
30
45
20
5
45
10


Bromegrass, Downy
70
5
20
60
70
60
0
60
50
45
5
50
40
85
25
5
40
70
30
20
60
35
50
5
65
80


Canarygrass
45
0
5
98
85
90
0
40
85
70
0
5
0
60
0
5
35
98
20
0
40
0
0
0
50
70


Chickweed
100
90
98
95
98
100
90
98
90
100
98
80
95
100
98
100
100
100
98
90
100
100
100
98
98
100


Cocklebur
98
85
90
90
85
90
75
95
90
100
85
75
95
95
45
90
90
40
95
95
80
95
95
85
98
65


Corn
85
15
25
85
80
85
10
70
80
75
15
80
45
90
75
75
80
75
15
10
85
60
55
75
75
65


Crabgrass, Large
95
85
98
90
98
100
85
95
90
100
75
85
90
98
70
95
98
100
95
90
95
95
100
85
95
95


Cupgrass, Woolly
95
55
85
90
95
98
20
85
95
95
60
65
65
98
75
75
75
90
100
50
65
75
80
40
75
75


Deadnettle
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Foxtail, Giant
98
75
95
85
90
95
75
95
98
95
75
80
80
100
95
90
90
98
95
80
90
85
95
80
95
95


Foxtail, Green
95
90
95
100
100
100
80
100
100
70
80
85
90
100
98
95
95
98
98
90
95
85
90
80
98
98



Galium

—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Goosegrass
98
70
90
85
85
85
75
90
90
95
80
75
75
90
95
80
95
95
90
70
80
85
98
85
80
85


Johnsongrass
95
10
70
98
95
100
20
100
100
100
10
10
15
100
65
10
100
98
100
45
75
85
75
10
75
45



Kochia

100
90
100
35
65
80
85
100
25
75
85
80
65
80
98
85
98
98
65
90
90
98
100
95
80
60


Lambsquarters
100
98
100
98
95
98
98
100
100
100
98
100
98
100
100
100
100
100
98
100
100
98
100
98
100
100


Morningglory
80
85
80
100
85
98
85
100
90
80
80
75
75
90
100
100
100
100
80
90
95
100
95
90
100
100


Nutsedge, Yellow
70
70
75
80
65
75
65
75
75
75
65
55
60
25
70
70
80
60
25
75
70
70
75
80
80
75


Oat, Wild
85
40
30
90
95
85
5
45
85
80
5
40
20
98
10
10
70
95
5
40
95
80
60
5
75
50


Pigweed
100
98
100
100
98
100
95
100
100
100
98
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100


Ragweed
98
90
98
95
85
98
98
75
98
95
90
80
80
90
60
90
95
80
95
95
85
90
95
85
98
75


Ryegrass, Italian
30
0
0
30
60
45
0
50
70
80
0
50
10
30
10
5
50
70
5
30
70
35
60
10
55
5


Soybean
98
85
95
95
98
95
75
98
95
95
50
95
85
98
98
98
98
98
98
95
95
95
98
70
98
95


Surinam Grass
98
70
85
90
98
98
60
100
98
90
75
70
75
98
98
25
90
100
85
100
85
75
85
80
90
65


Velvetleaf
100
98
100
95
100
98
100
98
95
98
98
100
98
100
100
100
100
100
95
100
100
100
100
100
100
100


Wheat
30
30
15
30
35
50
10
0
0
60
10
30
10
55
0
25
10
35
5
10
50
50
25
10
40
35


Windgrass
—
30
80
85
100
95
5
85
70
70
20
50
60
100
80
5
85
100
60
65
98
95
90
25
90
80












250 g ai/ha



Compounds


































81
82
83
85
86
87
88
89
90
91
92
93
94
95
96
97
98
99
100
102
107
108
109
111
113
117





Barley
5
5
5
20
65
5
80
20
20
40
0
5
5
0
5
5
15
30
50
60
30
0
5
30
20
0


Bermudagrass
95
95
90
90
95
100
85
95
85
95
85
85
98
90
98
98
98
98
85
100
98
100
95
100
95
100


Blackgrass
30
15
0
50
55
40
10
30
30
50
5
30
20
5
40
50
50
15
40
45
20
30
50
40
5
40


Bromegrass, Downy
50
30
60
30
50
80
60
5
10
30
20
0
0
0
10
10
40
25
35
30
30
5
5
10
90
45


Canarygrass
20
35
25
60
85
35
90
60
30
75
0
10
35
0
45
30
50
70
10
50
80
5
45
15
90
5


Chickweed
100
100
100
98
98
100
95
98
90
100
100
98
100
100
100
100
100
98
100
100
100
100
100
100
100
100


Cocklebur
90
100
90
98
98
100
95
70
100
95
98
98
90
100
100
100
100
100
98
100
100
100
100
100
98
100


Corn
65
15
25
85
85
75
80
98
75
60
60
60
80
35
80
75
70
80
45
70
85
65
60
60
85
25


Crabgrass, Large
98
90
98
95
98
98
98
98
80
100
100
90
90
80
90
95
95
95
80
90
95
85
85
85
95
95


Cupgrass, Woolly
90
75
95
90
95
90
95
75
55
98
70
70
70
65
85
75
95
85
75
85
80
75
75
75
95
98


Deadnettle
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Foxtail, Giant
98
95
98
98
98
95
95
98
85
98
98
85
98
85
85
90
85
95
85
95
95
80
90
70
95
95


Foxtail, Green
95
90
98
98
100
95
100
80
90
98
98
90
80
90
85
95
95
98
85
95
98
80
98
70
95
95



Galium

—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Goosegrass
80
85
95
85
95
98
70
80
75
85
90
75
85
90
85
98
90
80
75
90
85
85
85
85
90
85


Johnsongrass
100
95
100
98
100
45
100
100
65
100
100
70
45
45
80
85
98
95
25
75
90
60
75
40
95
25



Kochia

100
75
95
90
98
100
85
100
98
95
100
98
90
100
100
100
98
100
100
100
100
100
98
100
100
85


Lambsquarters
100
100
100
100
100
100
100
100
100
100
100
98
100
100
100
100
100
100
98
100
100
100
100
100
98
100


Morningglory
100
100
100
100
100
65
95
100
100
98
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100


Nutsedge, Yellow
80
55
85
85
85
75
75
75
75
75
75
70
65
85
85
80
75
75
40
80
85
85
80
85
75
35


Oat, Wild
55
10
10
60
80
90
80
50
20
50
10
5
30
0
30
10
50
80
30
80
40
0
40
10
85
35


Pigweed
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
98
98
100
100
100
100
100
100


Ragweed
100
95
98
98
98
98
98
100
95
98
75
98
80
95
95
100
90
95
80
95
98
98
98
98
98
98


Ryegrass, Italian
55
10
5
45
60
60
80
30
0
20
30
0
10
0
10
5
15
20
50
10
5
0
40
5
85
50


Soybean
98
98
95
95
98
100
98
98
100
98
98
98
95
98
98
100
100
100
100
100
100
85
100
98
98
95


Surinam Grass
100
80
90
85
100
85
98
95
75
98
75
70
80
70
85
85
90
80
75
85
85
80
80
80
90
85


Velvetleaf
100
95
100
98
100
100
98
100
100
100
100
98
80
100
100
100
98
100
85
100
100
100
100
100
98
100


Wheat
25
5
0
35
45
50
5
10
35
50
0
5
5
0
15
5
20
5
35
30
15
5
15
30
50
25


Windgrass
70
50
30
95
95
95
70
50
50
65
90
55
50
0
45
85
70
60
60
70
85
40
80
70
80
65












250 g ai/ha



Compounds


































118
119
120
121
123
126
127
128
129
130
140
141
146
147
152
155
156
157
160
162
164
173
181
184
186
187





Barley
0
5
5
10
50
40
60
5
0
0
0
5
30
0
90
85
85
30
50
85
35
50
55
60
5
40


Bermudagrass
98
98
98
100
98
95
98
100
98
95
90
90
100
98
98
100
98
100
95
100
100
100
100
100
98
100


Blackgrass
40
50
60
60
80
45
40
15
5
5
5
25
50
55
70
65
50
40
25
65
35
50
15
50
20
5


Bromegrass, Downy
35
85
80
90
45
40
40
50
35
40
20
45
35
10
85
50
40
65
55
50
95
70
85
60
50
40


Canarygrass
15
30
55
30
85
90
60
30
0
25
5
5
10
5
85
65
60
90
35
90
98
80
90
95
40
60


Chickweed
100
100
100
100
100
98
98
100
100
100
75
95
98
98
95
100
100
100
100
100
100
100
100
100
100
100


Cocklebur
98
95
80
100
100
98
100
100
100
100
95
100
—
100
100
100
98
100
100
100
100
100
100
100
100
100


Corn
25
70
75
85
80
80
75
60
60
80
45
45
35
40
80
65
60
100
60
85
70
85
95
98
65
80


Crabgrass, Large
95
95
98
98
90
90
95
100
85
100
90
85
98
90
95
90
80
100
95
98
100
100
100
100
95
100


Cupgrass, Woolly
95
100
100
100
90
90
85
95
85
90
65
70
75
80
100
75
65
98
95
100
100
100
100
100
85
95


Deadnettle
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
100
100
100


Foxtail, Giant
95
95
98
98
85
90
90
98
98
98
90
85
98
90
98
95
90
100
85
98
100
100
100
100
95
100


Foxtail, Green
95
100
100
100
90
95
95
98
95
98
95
90
90
90
100
80
85
95
98
100
100
90
98
98
95
98



Galium

—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
60
70
85


Goosegrass
90
95
98
98
85
85
85
98
95
95
85
80
95
95
98
98
80
100
90
98
98
100
100
100
100
100


Johnsongrass
35
80
80
85
90
90
95
85
85
80
45
65
95
60
100
70
65
100
75
100
98
—
100
100
100
100



Kochia

98
100
98
100
100
85
100
98
98
100
35
90
90
100
100
100
25
45
100
80
100
100
100
10
100
80


Lambsquarters
100
100
100
100
98
98
95
100
98
100
80
100
100
100
100
100
100
100
98
100
100
100
100
100
100
100


Morningglory
80
95
90
45
100
100
98
90
90
100
65
65
95
100
95
100
100
100
100
100
100
95
100
100
100
100


Nutsedge, Yellow
65
75
75
50
80
80
80
60
85
40
75
60
40
75
80
75
75
45
80
80
75
75
85
75
80
75


Oat, Wild
40
95
95
98
60
50
60
80
30
60
40
40
70
45
85
70
50
70
60
55
90
85
100
98
45
45


Pigweed
100
100
100
100
100
98
100
100
98
100
98
98
100
100
100
100
100
98
100
100
100
100
100
100
100
100


Ragweed
98
98
80
95
98
90
98
98
95
98
75
95
98
98
98
95
90
100
98
100
100
98
100
—
100
100


Ryegrass, Italian
60
85
80
75
50
50
30
30
0
5
5
5
15
40
80
60
40
35
35
90
40
30
65
60
30
30


Soybean
100
80
98
100
90
98
98
98
98
100
80
90
100
85
100
100
98
100
98
100
100
100
100
100
100
100


Surinam Grass
90
98
100
100
85
98
90
85
85
90
65
75
75
75
95
75
70
100
75
85
98
—
100
100
—
—


Velvetleaf
100
100
100
100
100
98
100
100
100
100
85
98
100
100
100
100
100
100
100
100
95
100
100
100
100
100


Wheat
10
60
80
80
50
50
40
5
0
10
15
10
45
10
90
70
45
30
45
40
50
50
70
60
5
5


Windgrass
80
100
90
100
90
60
70
85
85
85
30
50
60
70
98
85
60
80
80
80
85
75
65
100
65
80













250 g ai/ha
125 g ai/ha



Compounds
Compounds


































189
190
191
193
197
217
218
219
220
226
227
228
229
233
235
236
237
238
239
240
243
244
245
255
1
2





Barley
40
70
70
50
40
10
35
30
15
60
30
40
25
10
—
0
40
40
5
15
95
98
95
50
0
30


Bermudagrass
70
100
100
100
100
100
100
100
100
98
90
95
90
100
100
—
100
100
100
100
100
100
100
100
60
90


Blackgrass
5
40
60
60
45
30
5
90
40
60
20
55
30
50
—
40
80
70
50
65
98
85
80
60
5
45


Bromegrass, Downy
10
35
75
85
30
65
30
80
30
30
25
10
30
60
85
25
95
85
10
50
100
80
95
85
0
80


Canarygrass
10
55
85
25
60
20
5
55
30
60
10
10
60
20
30
10
50
30
0
40
100
100
100
60
0
80


Chickweed
100
100
100
100
100
100
100
100
100
95
90
100
98
100
100
100
100
100
100
100
100
100
100
100
65
95


Cocklebur
100
100
100
100
100
100
—
—
—
100
95
100
100
100
—
100
—
—
100
—
—
—
—
—
70
95


Corn
45
65
85
60
65
35
80
80
75
98
85
90
85
85
100
—
100
95
75
100
100
100
100
85
0
35


Crabgrass, Large
100
90
100
100
100
98
90
98
90
98
90
98
90
100
100
100
100
98
98
100
100
100
100
95
55
90


Cupgrass, Woolly
80
85
98
98
98
55
80
98
65
95
95
98
90
100
100
—
100
100
95
100
100
100
100
98
0
85


Deadnettle
100
100
100
100
100
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Foxtail, Giant
98
95
100
100
100
90
85
95
95
95
98
95
95
98
100
98
100
100
98
100
98
100
100
100
20
85


Foxtail, Green
95
70
98
80
70
90
90
90
90
90
90
100
95
100
98
98
95
98
95
98
100
100
100
90
30
100



Galium

85
85
60
90
80
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Goosegrass
90
98
100
100
100
95
35
95
90
85
80
90
80
98
100
100
98
98
100
98
98
98
100
98
65
95


Johnsongrass
70
80
100
80
100
65
80
100
90
100
65
100
100
25
100
55
100
100
—
100
100
100
100
95
0
98



Kochia

100
98
35
100
98
100
100
100
100
100
100
100
100
—
100
100
100
100
98
100
100
100
100
65
25
80


Lambsquarters
100
100
100
100
100
100
100
100
100
98
98
100
98
100
100
100
100
100
100
100
100
100
100
100
90
95


Morningglory
100
100
100
90
100
80
98
100
100
100
100
100
100
100
100
—
100
100
100
—
100
100
100
100
45
95


Nutsedge, Yellow
65
75
70
75
75
70
60
85
55
75
65
70
55
25
60
65
45
25
70
45
85
75
75
60
20
75


Oat, Wild
25
50
80
75
85
85
60
85
50
50
30
40
35
60
95
60
90
60
30
60
100
98
100
90
10
55


Pigweed
100
100
100
100
100
100
100
100
100
98
100
100
100
—
100
—
100
100
100
100
100
100
100
100
85
95


Ragweed
80
—
—
—
—
98
100
100
98
90
85
98
95
98
100
98
100
100
100
100
100
100
100
95
70
90


Ryegrass, Italian
5
30
50
45
35
40
70
40
60
20
10
0
10
60
60
5
60
70
0
40
95
95
85
80
0
40


Soybean
100
98
100
100
100
98
100
100
100
100
98
100
98
100
100
100
100
100
98
100
100
100
100
100
70
95


Surinam Grass
85
90
98
95
70
95
90
65
75
85
95
98
90
100
100
—
100
100
75
100
100
100
100
90
10
85


Velvetleaf
100
100
100
100
100
100
100
98
100
98
98
100
85
100
100
100
100
100
100
100
100
100
100
100
85
90


Wheat
0
30
65
60
40
50
0
50
15
30
20
35
35
65
80
60
85
80
30
50
100
95
98
80
0
20


Windgrass
80
65
100
75
98
85
45
85
60
85
50
90
65
60
98
85
100
95
70
98
100
95
98
95
0
50












125 g ai/ha



Compounds




































3
4
7
8
9
10
11
12
14
24
26
27
29
33
34
36
37
38
39
40
42
44
45
46
47
48
49
50





Barley
0
0
0
5
20
0
10
0
5
50
0
10
0
0
30
20
0
0
0
10
0
5
5
0
10
10
0
5


Bermudagrass
70
85
65
95
98
90
100
98
80
100
60
100
90
98
95
100
98
100
85
100
95
95
95
90
98
98
95
100


Blackgrass
0
30
0
10
40
50
40
10
5
40
10
45
40
30
10
15
5
15
0
10
15
30
10
10
25
20
0
5


Bromegrass, Downy
0
50
5
10
40
10
45
20
50
70
20
20
40
10
50
45
15
85
0
70
15
80
45
10
50
50
0
20


Canarygrass
0
75
0
70
50
5
90
5
20
—
50
30
40
5
50
50
10
10
0
30
0
30
30
0
40
45
0
5


Chickweed
98
100
90
100
95
95
100
100
80
95
85
50
50
100
98
100
85
100
100
100
80
98
98
95
100
95
80
98


Cocklebur
85
100
65
100
35
95
100
100
90
98
95
95
95
95
85
—
—
—
95
—
85
90
70
80
95
98
80
90


Corn
10
50
0
75
75
45
80
45
45
85
40
50
50
10
45
65
60
75
45
85
20
80
60
60
80
85
5
25


Crabgrass, Large
80
100
45
90
85
75
100
80
85
95
50
60
55
90
95
95
85
98
85
100
85
95
75
75
90
95
80
95


Cupgrass, Woolly
20
100
50
90
80
70
90
70
80
95
85
70
85
70
90
95
75
95
85
98
25
85
75
25
90
90
55
80


Deadnettle
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Foxtail, Giant
60
98
55
100
95
80
98
98
80
90
70
90
90
85
95
98
95
100
95
100
75
95
95
80
98
95
70
95


Foxtail, Green
35
60
30
85
80
70
85
70
50
90
85
80
75
90
90
90
85
95
90
95
60
90
85
85
95
95
75
95



Galium

—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Goosegrass
70
85
35
95
90
95
95
98
80
85
95
98
85
85
90
90
85
90
65
95
90
90
80
80
95
95
70
90


Johnsongrass
—
95
0
98
85
60
90
60
80
70
50
45
40
35
95
85
60
95
90
75
40
90
98
70
98
80
10
65



Kochia

85
100
45
100
25
15
75
60
—
80
—
100
—
95
100
60
15
100
60
10
100
75
15
20
98
100
80
100


Lambsquarters
98
100
65
100
80
90
95
98
85
90
90
95
90
98
100
100
98
100
100
100
100
95
100
90
98
100
90
100


Morningglory
55
90
15
100
70
45
70
70
80
60
75
80
80
80
85
75
75
75
75
75
75
75
80
45
90
80
80
70


Nutsedge, Yellow
65
75
0
80
60
60
50
65
30
30
35
50
70
75
55
25
25
15
15
55
70
50
45
70
70
60
70
70


Oat, Wild
5
50
0
35
40
20
70
20
50
60
45
50
60
40
60
75
40
80
30
90
10
80
60
20
60
85
5
10


Pigweed
100
100
90
100
100
95
85
98
80
80
85
100
80
98
98
90
98
98
100
100
100
98
100
80
100
100
95
100


Ragweed
98
100
80
100
75
90
100
100
85
90
98
100
100
98
95
95
95
80
95
98
85
95
95
80
95
90
80
98


Ryegrass, Italian
5
15
0
30
30
0
40
5
5
40
10
5
40
40
20
10
5
60
5
0
10
10
35
5
30
30
0
0


Soybean
80
100
75
98
85
95
100
100
90
95
95
95
98
98
95
100
95
90
98
100
95
95
98
90
98
98
85
95


Surinam Grass
40
75
20
75
75
70
85
65
50
60
60
80
70
75
80
85
75
90
65
98
45
95
95
80
98
95
55
80


Velvetleaf
100
90
90
95
90
75
100
98
90
98
95
80
80
98
98
100
95
100
80
100
95
100
90
85
98
98
98
98


Wheat
10
50
10
35
30
0
40
0
0
30
5
10
10
5
35
5
0
40
5
30
5
30
15
0
5
10
15
5


Windgrass
0
60
5
30
60
30
85
45
30
60
40
50
30
30
50
80
50
85
5
80
70
85
70
15
80
90
5
60












125 g ai/ha



Compounds




































51
52
53
55
56
58
59
61
62
63
64
66
67
68
69
70
71
72
73
74
75
77
79
80
81
82
83
85





Barley
30
25
70
0
30
5
10
0
5
0
—
0
20
25
15
90
0
0
0
0
0
0
35
30
0
0
5
20


Bermudagrass
90
95
98
85
100
98
98
90
85
85
98
95
70
95
98
95
80
85
90
95
98
95
85
45
95
85
85
90


Blackgrass
50
25
40
5
20
20
40
0
30
35
5
10
5
0
0
35
0
0
10
25
0
0
30
5
30
5
0
35


Bromegrass, Downy
55
60
55
0
50
45
35
0
50
20
60
20
0
25
70
70
10
0
50
5
35
5
30
60
30
5
45
25


Canarygrass
60
65
90
0
40
80
50
0
0
0
40
0
0
35
25
85
5
0
5
0
0
0
35
50
10
15
25
55


Chickweed
85
95
98
80
98
90
98
95
75
80
98
95
95
98
98
98
95
90
95
95
98
95
95
100
98
98
98
95


Cocklebur
90
85
85
65
75
85
90
70
55
90
95
25
90
90
20
40
95
90
65
90
95
60
98
45
65
95
80
98


Corn
80
65
80
5
65
65
75
10
75
25
85
70
65
80
25
60
0
5
80
15
20
60
60
65
15
5
15
85


Crabgrass, Large
85
90
95
80
90
90
95
75
80
80
98
65
90
90
98
95
80
85
90
95
100
75
90
90
95
80
95
90


Cupgrass, Woolly
80
85
95
15
65
70
90
60
60
65
98
60
70
55
95
90
85
50
65
55
55
35
65
70
90
65
90
90


Deadnettle
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Foxtail, Giant
85
90
90
55
85
90
95
65
75
65
98
80
85
85
98
95
80
75
80
70
85
75
95
95
95
95
95
90


Foxtail, Green
95
98
100
80
98
98
70
60
80
70
100
90
80
85
100
98
70
90
90
80
90
80
80
95
95
85
98
95



Galium

—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Goosegrass
85
85
80
65
75
85
95
65
65
70
85
70
65
85
85
85
90
65
75
80
95
75
70
80
70
80
80
80


Johnsongrass
85
90
95
10
85
98
100
10
0
10
100
65
5
75
100
80
98
40
70
10
20
10
70
10
75
80
100
95



Kochia

25
55
75
75
100
25
45
70
60
25
80
90
85
95
80
75
25
90
90
95
100
95
75
20
90
65
80
85


Lambsquarters
95
90
98
95
100
100
100
95
98
98
100
95
98
100
100
100
90
100
100
95
100
98
100
98
100
100
100
98


Morningglory
90
75
80
75
100
90
80
70
75
75
85
100
95
98
75
100
75
90
75
95
95
80
100
100
100
100
85
100


Nutsedge, Yellow
75
45
75
55
75
55
70
60
35
50
10
65
65
70
40
40
10
65
50
70
70
70
70
55
80
45
70
85


Oat, Wild
60
95
85
0
40
60
55
0
25
5
95
5
10
50
85
90
0
30
80
60
50
5
60
40
50
5
10
25


Pigweed
98
95
100
90
100
98
100
90
100
95
100
100
98
100
100
98
98
100
100
100
100
100
100
100
100
100
100
100


Ragweed
90
80
95
95
75
90
90
85
75
80
90
25
85
80
100
75
80
90
85
85
90
80
95
65
98
95
85
85


Ryegrass, Italian
10
55
40
0
50
30
70
0
50
0
0
5
5
15
50
50
0
10
60
20
40
5
50
5
45
5
0
35


Soybean
95
95
95
60
95
95
95
10
90
85
98
98
98
98
98
95
95
85
90
95
98
70
95
90
95
95
90
90


Surinam Grass
90
90
98
45
85
95
90
75
65
35
98
85
20
70
100
95
65
80
85
65
70
75
75
60
98
75
85
85


Velvetleaf
90
98
95
98
98
85
95
95
95
98
98
98
98
100
98
100
90
100
100
100
100
98
98
100
100
90
95
98


Wheat
10
35
30
5
0
0
10
0
5
0
30
0
25
5
10
35
0
10
40
30
10
10
35
20
25
0
0
20


Windgrass
60
90
85
0
60
60
60
0
35
40
95
70
5
65
80
90
45
60
90
80
70
20
65
70
60
20
15
80












125 g ai/ha



Compounds


































86
87
88
89
90
91
92
93
94
95
96
97
98
99
100
102
107
108
109
111
113
117
118
119
120
121





Barley
60
0
40
10
10
30
0
5
5
0
0
0
10
10
30
30
25
0
5
5
5
0
0
5
5
5


Bermudagrass
95
98
80
95
85
95
85
85
98
75
95
95
85
80
75
85
95
100
90
100
95
95
98
98
98
100


Blackgrass
45
20
5
20
5
30
5
30
10
0
30
30
20
5
10
30
15
20
40
25
5
40
35
50
60
40


Bromegrass, Downy
35
60
45
5
10
5
20
0
0
0
5
5
5
25
15
10
10
5
5
5
80
15
30
60
60
80


Canarygrass
80
35
80
50
30
65
0
5
30
0
30
10
35
60
5
30
60
5
30
0
—
5
10
30
55
5


Chickweed
95
100
95
98
85
98
98
95
100
98
98
100
98
98
95
95
100
100
98
100
100
98
95
100
85
100


Cocklebur
95
100
95
65
100
95
98
95
60
100
98
100
100
100
95
100
100
100
100
100
98
98
85
80
25
85


Corn
80
75
65
98
45
45
45
50
70
25
65
60
55
65
20
65
75
50
60
55
80
25
20
60
50
55


Crabgrass, Large
98
95
98
95
75
98
98
80
90
75
85
85
80
95
75
85
90
75
75
80
95
95
80
95
95
95


Cupgrass, Woolly
95
75
90
65
50
98
65
65
65
65
85
70
75
80
70
75
75
70
60
75
95
95
75
98
100
100


Deadnettle
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Foxtail, Giant
98
85
95
90
75
98
90
80
85
75
80
85
85
95
80
80
85
75
80
65
90
80
85
95
85
98


Foxtail, Green
100
90
100
70
80
98
98
80
70
65
70
85
85
95
80
90
90
80
85
65
80
80
95
95
95
100



Galium

—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Goosegrass
85
95
70
75
75
85
75
65
75
75
85
80
80
75
75
80
75
75
80
85
85
75
80
85
85
98


Johnsongrass
100
35
100
100
30
95
98
50
45
15
70
75
75
80
10
60
70
20
50
20
90
—
20
75
75
—



Kochia

98
100
80
85
85
85
95
95
80
100
95
98
80
100
98
100
100
98
85
100
100
—
70
95
80
—


Lambsquarters
100
100
100
98
100
100
100
95
100
98
100
100
100
100
98
100
100
100
100
100
98
100
100
100
98
100


Morningglory
90
65
95
90
100
98
100
95
100
100
100
100
100
100
100
100
100
100
100
100
100
80
70
95
80
25


Nutsedge, Yellow
75
70
70
70
70
75
70
70
60
85
85
80
70
70
15
75
75
80
75
80
75
25
65
65
65
45


Oat, Wild
60
65
70
20
10
45
5
0
5
0
25
5
20
40
30
40
20
0
30
0
45
30
10
95
80
98


Pigweed
100
—
100
100
100
100
100
98
100
100
98
100
100
100
98
95
100
100
100
100
100
—
100
100
100
100


Ragweed
95
98
95
95
85
95
75
85
65
95
95
100
80
80
75
85
95
95
95
98
98
90
95
95
75
90


Ryegrass, Italian
50
40
30
20
0
10
5
0
0
0
10
0
15
20
10
5
5
0
5
0
50
15
5
60
60
70


Soybean
98
100
98
98
98
95
98
95
95
98
75
95
98
100
100
95
100
65
98
95
98
95
95
60
95
95


Surinam Grass
98
—
95
80
70
98
70
70
65
45
75
80
85
75
65
75
80
65
65
70
90
—
75
95
100
100


Velvetleaf
100
100
95
98
100
100
100
95
75
100
98
100
95
100
70
100
100
100
100
100
98
95
98
100
98
100


Wheat
40
50
5
5
15
35
0
0
0
0
10
0
5
5
15
20
5
0
5
5
40
20
5
60
60
45


Windgrass
85
85
65
30
5
50
80
50
45
0
45
60
50
10
45
60
80
30
60
35
35
65
70
100
90
100












125 g ai/ha



Compounds


































122
123
126
127
128
129
130
131
140
141
146
147
152
155
156
157
160
162
164
169
173
181
184
186
187
189





Barley
50
25
15
35
0
0
0
0
0
5
15
0
85
45
60
30
35
50
30
0
35
50
60
5
40
15


Bermudagrass
85
90
90
98
98
95
90
85
85
85
100
95
98
98
95
100
90
100
98
100
100
100
100
95
100
65


Blackgrass
15
40
30
25
10
5
5
0
5
10
35
45
55
60
35
10
20
55
10
10
30
15
40
5
5
5


Bromegrass, Downy
50
10
30
20
40
15
35
0
5
10
10
5
60
35
35
60
50
45
85
90
40
60
50
30
35
5


Canarygrass
45
55
60
35
30
0
20
0
5
5
5
5
80
50
40
80
20
90
90
80
40
85
80
40
55
5


Chickweed
80
95
98
98
95
90
100
90
45
90
98
98
90
100
100
100
95
100
98
100
100
100
100
100
100
100


Cocklebur
85
100
80
95
100
98
95
100
65
95
—
90
98
98
75
100
100
100
100
100
100
100
100
100
100
100


Corn
25
75
55
25
60
60
80
20
25
45
20
25
65
40
45
95
50
80
45
55
60
95
85
30
75
35


Crabgrass, Large
85
85
85
90
95
85
95
80
80
80
85
85
95
80
65
98
95
98
98
100
95
100
100
85
100
95


Cupgrass, Woolly
75
75
85
85
90
85
85
65
65
65
65
80
98
65
55
98
85
100
98
100
100
100
100
80
85
75


Deadnettle
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
100
100
—
100


Foxtail, Giant
80
80
85
85
98
90
98
80
80
80
95
85
95
90
85
100
75
98
98
100
100
100
100
95
100
90


Foxtail, Green
85
85
90
90
95
90
95
95
85
90
80
80
98
80
85
85
70
98
98
95
90
95
85
85
98
90



Galium

—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
60
70
55
85


Goosegrass
70
80
75
75
98
90
95
75
70
75
95
80
95
85
70
98
90
90
98
100
95
100
100
98
100
90


Johnsongrass
75
75
85
80
85
70
80
50
35
50
70
60
95
65
45
100
65
100
95
65
95
100
100
75
100
65



Kochia

45
80
25
100
95
95
100
75
10
85
85
80
95
100
20
10
100
75
100
100
98
100
5
100
70
98


Lambsquarters
90
98
85
90
100
95
100
98
75
98
100
98
98
100
95
100
98
98
100
100
100
100
100
100
100
100


Morningglory
85
100
100
90
90
90
100
75
65
60
85
65
75
100
100
95
100
90
98
100
80
100
100
100
100
100


Nutsedge, Yellow
75
75
80
75
60
60
35
45
65
60
20
70
80
70
70
40
80
75
70
55
60
80
45
75
65
55


Oat, Wild
35
30
35
25
60
20
40
0
10
15
50
20
80
60
35
60
50
45
85
85
70
90
80
20
45
10


Pigweed
98
100
98
95
98
98
100
100
75
95
100
100
100
100
98
90
100
100
100
100
100
100
75
100
100
100


Ragweed
75
95
85
98
95
95
98
95
65
85
98
90
95
90
75
100
98
100
98
100
90
100
—
100
100
75


Ryegrass, Italian
40
5
5
5
5
0
0
0
0
0
10
30
45
40
20
30
35
80
20
10
30
60
45
0
10
5


Soybean
80
85
85
98
98
98
98
98
75
75
98
65
98
100
98
100
98
100
100
95
95
100
100
100
100
98


Surinam Grass
90
85
85
85
85
85
80
65
55
70
75
75
90
65
60
98
60
75
95
—
—
95
100
—
—
80


Velvetleaf
98
95
95
100
95
95
98
98
80
98
98
95
100
100
95
100
100
95
80
100
100
100
100
100
100
100


Wheat
50
15
35
25
0
0
5
0
10
5
15
5
85
40
35
20
40
35
35
5
40
50
55
0
5
0


Windgrass
50
80
40
55
70
80
75
5
5
40
60
55
85
70
55
70
60
60
75
55
70
60
90
50
65
60













125 g ai/ha
62 g ai/ha



Compounds
Compounds


































190
191
193
197
217
218
219
220
225
226
227
228
229
233
235
236
237
238
239
240
243
244
245
255
1
2





Barley
40
50
50
10
10
35
30
10
40
30
5
40
5
10
40
0
40
35
5
15
95
90
85
35
0
20


Bermudagrass
100
100
100
100
98
95
100
98
85
85
85
90
85
100
100
98
100
100
100
100
100
100
100
95
50
85


Blackgrass
35
50
40
10
30
5
55
30
15
40
5
50
5
30
70
30
70
60
30
65
85
65
80
10
0
30


Bromegrass, Downy
35
50
40
30
40
20
80
15
85
5
0
10
20
50
50
10
90
50
5
25
95
75
95
80
0
60


Canarygrass
25
60
25
40
20
0
55
10
85
50
5
5
50
10
30
0
50
30
0
30
100
98
100
50
0
50


Chickweed
100
98
100
100
100
100
100
98
95
85
80
100
90
100
100
100
100
100
98
100
100
98
100
100
60
90


Cocklebur
95
98
100
100
98
—
—
—
100
100
95
100
100
100
—
100
—
—
100
—
—
—
—
—
65
90


Corn
40
75
40
45
25
75
75
55
70
98
75
85
85
85
100
70
100
95
45
100
100
95
100
85
0
25


Crabgrass, Large
80
100
98
98
90
70
95
85
95
95
85
98
90
98
98
98
100
98
95
100
100
100
100
90
50
85


Cupgrass, Woolly
80
90
95
90
45
60
95
65
85
85
90
95
80
100
100
95
100
100
95
100
100
100
100
95
0
80


Deadnettle
100
100
100
100
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Foxtail, Giant
90
100
95
98
85
65
80
55
85
95
90
95
80
98
100
95
98
100
90
100
98
95
100
98
15
85


Foxtail, Green
45
80
60
50
85
90
90
80
98
90
90
98
80
95
95
98
95
98
90
95
100
98
100
90
10
90



Galium

60
60
90
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Goosegrass
80
100
98
100
85
15
95
85
95
85
75
85
70
98
98
95
98
98
98
98
98
98
100
95
60
90


Johnsongrass
75
100
70
95
60
55
98
80
75
100
60
95
100
25
100
20
100
98
60
100
100
100
100
90
0
90



Kochia

98
25
100
95
100
100
98
75
15
100
85
100
80
—
100
100
100
100
98
100
100
100
100
15
20
75


Lambsquarters
100
98
98
100
100
100
100
100
98
95
98
100
95
100
100
100
100
100
100
100
100
100
100
98
75
90


Morningglory
85
90
65
100
80
80
100
98
95
100
100
100
100
98
100
95
100
100
100
—
100
100
100
85
20
80


Nutsedge, Yellow
65
55
75
65
70
15
70
25
25
70
65
60
40
25
55
15
45
20
65
20
70
65
70
15
20
60


Oat, Wild
40
70
70
70
50
60
80
30
85
50
10
15
10
45
85
20
60
50
5
45
85
95
85
85
5
45


Pigweed
100
98
100
98
100
100
100
100
98
98
100
100
95
—
100
98
100
100
98
100
100
100
100
98
80
90


Ragweed
—
—
—
—
85
98
98
98
90
85
70
95
80
98
100
98
100
100
100
100
98
98
100
95
70
80


Ryegrass, Italian
20
50
40
30
40
60
40
30
40
5
5
0
0
50
55
0
60
25
0
40
85
80
70
30
0
40


Soybean
95
100
98
100
95
100
100
90
98
100
95
100
98
100
100
98
100
100
98
95
100
100
100
100
65
90


Surinam Grass
75
90
80
65
80
85
35
60
85
80
80
95
80
100
100
75
100
100
45
100
100
100
100
90
0
75


Velvetleaf
100
90
100
100
100
100
95
95
90
90
98
100
85
95
100
100
100
100
100
85
100
100
100
98
75
85


Wheat
30
55
60
5
50
0
50
0
55
25
10
20
5
60
80
30
85
80
5
50
95
85
95
50
0
10


Windgrass
65
85
70
50
80
45
60
40
80
70
40
80
50
60
95
70
98
85
30
98
98
80
95
80
0
15












62 g ai/ha



Compounds









































3
4
7
8
9
10
11
12
14
24
26
27
29
33
34
36
37
38
39
40
42
44
45
46
47
48
49
50
51
52
53
55
56





Barley
0
0
0
0
0
0
10
0
0
5
0
0
0
0
30
10
0
0
0
0
0
0
5
0
10
5
0
0
25
0
50
0
10


Bermudagrass
25
85
45
85
95
75
100
85
70
95
50
90
90
95
95
98
90
100
60
100
75
95
85
85
—
95
85
100
90
95
95
80
85


Blackgrass
0
20
0
10
0
0
5
10
0
10
0
5
20
15
5
5
0
15
0
10
10
10
5
5
20
5
0
5
30
5
30
0
10


Bromegrass, Downy
0
15
0
5
30
0
35
10
30
50
15
5
10
5
50
30
10
70
0
50
5
70
20
5
40
25
0
5
50
55
50
0
45


Canarygrass
0
20
0
50
25
0
50
5
20
40
30
10
20
0
50
45
5
10
0
20
0
20
10
0
30
30
0
0
60
50
80
0
30


Chickweed
98
100
80
100
85
95
98
100
—
90
50
45
50
98
75
98
80
90
100
100
70
95
85
95
98
90
75
80
80
95
98
75
95


Cocklebur
80
100
45
100
0
90
100
98
90
98
80
95
95
90
25
—
—
—
75
—
45
80
50
80
—
95
80
85
85
85
85
60
55


Corn
0
25
0
65
45
15
75
30
40
50
35
40
35
10
0
55
15
70
45
80
10
80
45
35
—
70
5
10
80
45
80
5
65


Crabgrass, Large
70
85
45
85
80
70
85
75
55
75
50
50
50
85
85
95
75
90
80
98
75
90
75
65
85
85
75
85
85
90
95
75
85


Cupgrass, Woolly
15
95
50
80
75
70
75
60
80
80
40
60
85
65
80
90
65
90
85
95
20
80
75
20
90
80
50
75
75
75
90
10
45


Deadnettle
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Foxtail, Giant
45
98
55
100
85
75
85
90
70
85
60
85
90
80
90
95
85
98
85
100
65
95
90
80
98
85
60
85
80
80
85
30
80


Foxtail, Green
10
40
20
70
40
25
60
60
45
40
40
80
75
85
90
90
65
90
80
95
55
90
80
60
90
95
50
80
95
98
100
40
85



Galium

—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Goosegrass
50
75
25
85
85
75
85
85
80
85
90
90
85
75
80
85
85
85
55
90
85
90
75
75
95
85
70
80
80
80
80
60
75


Johnsongrass
0
80
0
98
70
55
70
60
80
60
50
45
20
35
90
75
40
75
65
—
0
70
90
50
—
80
0
10
75
85
95
0
80



Kochia

80
100
45
100
15
15
25
20
—
70
—
—
—
80
95
0
0
80
45
0
100
75
0
0
95
98
65
100
20
25
65
65
95


Lambsquarters
95
100
65
100
80
80
70
85
85
90
90
95
85
98
98
100
98
95
95
100
95
95
98
85
98
95
80
98
90
85
95
80
98


Morningglory
20
85
15
90
45
45
15
60
70
60
50
80
70
60
80
70
70
70
75
—
70
70
75
30
80
70
80
25
80
45
75
60
—


Nutsedge, Yellow
45
65
0
70
25
55
35
55
30
30
30
40
50
50
25
20
15
0
0
35
60
50
10
70
65
45
65
70
65
25
65
10
70


Oat, Wild
0
50
0
15
5
5
50
5
40
50
40
50
50
15
50
75
10
75
20
85
10
80
55
5
60
50
5
5
60
90
70
0
20


Pigweed
90
100
75
100
85
85
80
95
80
80
80
98
65
95
90
85
85
98
100
98
95
95
98
75
98
85
90
98
95
90
95
85
98


Ragweed
85
100
65
100
75
80
100
100
80
80
85
98
85
95
85
90
80
80
85
98
75
95
85
75
90
85
80
90
80
80
85
80
55


Ryegrass, Italian
0
10
0
20
0
0
10
0
5
5
0
5
20
10
10
5
0
50
5
0
5
5
30
5
30
5
0
0
0
45
5
0
0


Soybean
70
100
65
98
75
95
100
100
85
95
95
95
95
98
95
98
80
85
95
100
90
95
95
80
95
95
65
85
90
95
95
60
85


Surinam Grass
25
70
10
65
65
70
70
55
50
55
40
70
50
65
75
85
70
85
65
95
40
95
75
75
95
85
30
75
85
85
95
15
80


Velvetleaf
100
75
80
80
85
70
95
85
90
90
70
60
55
90
95
100
80
100
80
100
80
98
80
80
85
85
95
98
85
98
85
98
90


Wheat
0
5
0
30
5
0
35
0
0
10
0
5
0
0
10
5
0
20
5
20
0
10
15
0
0
0
5
5
10
25
25
0
0


Windgrass
0
55
5
20
55
10
85
40
30
30
30
10
10
25
40
70
30
80
0
70
60
70
60
10
—
80
0
50
60
80
80
0
40












62 g ai/ha



Compounds





































58
59
61
62
63
64
66
67
68
69
70
71
72
73
74
75
77
79
80
81
82
83
85
86
87
88
89
90
91





Barley
5
0
0
5
0
—
0
5
0
5
30
0
0
0
0
0
0
30
30
0
0
5
10
40
0
30
5
5
30


Bermudagrass
85
90
90
80
85
95
70
70
75
98
85
75
80
80
80
98
90
80
40
85
85
75
85
90
90
80
85
80
95


Blackgrass
10
35
0
30
35
0
10
0
0
0
35
0
0
10
0
0
0
15
0
10
0
0
35
30
5
5
15
5
20


Bromegrass, Downy
40
30
0
45
20
45
10
0
5
55
50
5
0
45
5
20
5
10
60
5
0
45
5
10
50
45
0
5
5


Canarygrass
60
5
0
0
0
40
0
0
0
0
80
5
0
0
0
0
0
30
50
5
0
20
40
20
30
70
35
10
55


Chickweed
80
98
80
70
65
98
85
95
90
98
90
90
85
80
85
90
85
95
98
98
90
90
95
95
100
85
80
80
95


Cocklebur
85
85
65
55
80
95
10
75
75
0
0
65
80
45
85
80
0
98
10
55
90
80
95
95
100
90
60
90
65


Corn
45
0
0
70
20
85
55
10
15
10
35
0
0
80
0
0
5
45
35
10
5
5
70
60
55
65
95
25
35


Crabgrass, Large
80
85
65
75
75
90
55
80
90
95
90
75
80
85
80
98
60
85
80
95
75
85
90
98
85
98
95
75
95


Cupgrass, Woolly
65
75
55
55
60
95
40
70
10
95
65
45
45
65
10
55
20
40
70
75
55
85
85
85
75
80
50
45
85


Deadnettle
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Foxtail, Giant
85
90
65
65
65
95
75
80
80
98
85
75
70
75
55
80
75
75
90
85
80
95
80
95
80
95
85
70
98


Foxtail, Green
90
70
55
70
70
85
85
80
85
98
85
60
70
90
20
85
80
60
95
85
60
95
95
95
80
98
70
65
85



Galium

—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Goosegrass
75
80
50
65
70
80
65
55
70
80
85
75
65
75
75
80
75
65
75
70
75
80
70
75
80
70
65
60
75


Johnsongrass
85
75
0
0
10
98
60
0
10
100
70
75
10
65
0
10
0
65
0
10
80
100
95
98
25
100
90
25
90



Kochia

10
10
25
25
25
55
85
80
90
70
65
0
85
80
75
95
80
75
20
80
60
75
85
85
100
75
75
85
80


Lambsquarters
95
98
95
95
95
100
95
95
98
100
98
85
100
98
95
100
98
98
95
98
95
98
98
100
98
98
98
95
100


Morningglory
80
50
70
15
70
80
100
90
85
70
100
65
85
50
85
90
75
95
100
90
100
75
100
80
45
90
85
95
90


Nutsedge, Yellow
40
60
60
25
20
10
45
65
10
10
15
10
65
20
20
65
60
60
15
80
15
20
85
70
60
65
55
65
65


Oat, Wild
60
40
0
10
0
90
0
5
20
80
70
0
—
80
20
20
5
45
30
35
0
10
25
50
60
55
10
5
30


Pigweed
95
100
85
98
95
100
98
98
95
100
98
85
100
98
98
100
98
100
100
100
98
90
100
100
98
100
98
98
100


Ragweed
85
80
80
75
75
85
10
80
80
90
70
80
80
80
75
85
75
85
60
80
80
80
85
90
95
80
85
75
85


Ryegrass, Italian
0
50
0
5
0
0
0
5
5
50
10
0
0
45
20
15
5
20
0
5
0
0
10
30
10
5
5
0
5


Soybean
85
95
0
80
75
98
95
90
95
90
75
70
80
85
75
95
50
90
80
95
90
90
85
95
98
90
90
98
85


Surinam Grass
80
80
65
45
25
95
70
20
55
90
65
55
80
85
45
50
65
45
45
90
65
75
85
95
75
95
75
65
98


Velvetleaf
75
90
80
95
98
98
90
95
100
98
80
85
100
100
100
100
98
98
100
100
90
90
98
100
100
90
95
98
100


Wheat
0
5
0
0
0
15
—
5
5
5
20
0
5
35
5
0
5
25
10
20
0
0
5
35
35
5
5
10
10


Windgrass
50
60
0
35
30
90
60
0
50
60
85
10
20
80
60
50
10
65
60
50
5
10
70
60
60
60
5
5
40












62 g ai/ha



Compounds


































92
93
94
95
96
97
98
99
100
102
107
108
109
111
113
117
118
119
120
121
122
123
126
127
128
129





Barley
0
0
0
0
0
0
5
5
20
10
5
0
0
0
5
0
0
0
5
5
10
10
5
20
0
0


Bermudagrass
80
75
80
75
95
95
80
75
70
85
80
90
85
100
90
90
95
98
95
98
80
85
85
95
85
80


Blackgrass
0
5
10
0
20
20
5
0
5
5
5
5
5
5
0
10
10
20
30
40
5
20
25
20
5
5


Bromegrass, Downy
5
0
0
0
0
0
5
5
10
10
5
0
0
0
60
10
5
30
60
50
5
5
15
10
35
10


Canarygrass
0
0
5
0
5
10
20
60
5
20
15
5
0
0
90
0
0
5
30
5
35
40
40
10
10
0


Chickweed
95
80
100
85
95
100
80
98
75
80
100
100
98
100
98
95
95
80
75
100
70
75
80
75
90
85


Cocklebur
80
90
45
95
95
100
100
100
85
95
100
95
98
98
95
75
40
10
15
45
45
80
65
95
98
98


Corn
35
45
55
0
60
40
35
65
10
15
65
35
15
45
60
15
0
45
20
55
15
70
30
25
50
35


Crabgrass, Large
90
80
75
65
80
80
75
85
60
80
85
70
75
75
90
80
75
85
85
90
75
80
80
85
85
80


Cupgrass, Woolly
25
45
65
55
75
60
70
75
65
75
65
60
60
50
85
85
70
98
75
100
70
45
75
75
90
85


Deadnettle
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Foxtail, Giant
75
80
75
65
70
75
75
80
75
75
80
60
75
65
85
75
80
85
80
98
75
75
80
85
95
85


Foxtail, Green
80
60
60
50
65
85
85
90
70
90
75
30
80
60
80
70
85
90
95
90
85
60
80
85
95
90



Galium

—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Goosegrass
70
65
70
75
70
70
75
75
70
70
75
70
75
70
75
75
65
75
80
98
65
65
70
75
95
85


Johnsongrass
85
10
15
10
45
55
70
75
5
25
70
20
30
15
85
20
10
40
25
70
65
65
65
70
70
45



Kochia

90
85
55
100
85
90
70
80
95
70
98
95
75
100
100
50
65
75
40
100
0
65
25
98
85
95


Lambsquarters
98
95
95
98
98
100
98
100
98
98
100
98
98
98
98
98
98
100
85
100
65
95
85
85
98
95


Morningglory
95
80
75
100
95
100
85
100
100
100
100
90
98
100
100
75
60
60
50
20
75
98
85
80
80
90


Nutsedge, Yellow
65
60
20
75
70
75
60
70
5
65
75
75
65
75
75
0
45
50
35
45
70
75
75
70
35
35


Oat, Wild
5
0
5
0
5
5
20
20
10
15
5
0
0
0
40
10
5
60
80
90
30
5
10
10
50
5


Pigweed
100
95
100
98
95
100
100
100
98
70
100
98
100
100
100
98
100
98
98
100
90
98
95
95
98
95


Ragweed
60
75
45
80
80
98
75
80
70
80
85
85
95
95
95
75
85
75
75
85
60
85
75
85
85
95


Ryegrass, Italian
0
0
0
0
5
0
5
0
5
0
0
0
0
0
45
10
5
30
40
40
10
5
5
5
0
0


Soybean
98
80
80
98
75
80
98
100
98
85
98
55
95
80
98
80
90
50
80
90
75
75
75
98
98
98


Surinam Grass
65
65
60
45
75
75
75
70
65
75
75
60
65
—
85
75
—
85
85
100
75
75
80
75
80
85


Velvetleaf
100
90
70
95
98
100
95
100
70
100
100
100
98
98
95
85
75
80
95
98
90
90
90
95
95
95


Wheat
0
0
0
0
5
0
5
5
5
10
5
0
5
0
15
5
5
40
40
45
30
15
15
10
0
0


Windgrass
50
10
40
0
10
50
20
5
40
10
40
10
40
30
30
45
60
85
80
98
30
60
10
50
65
60












62 g ai/ha



Compounds


































130
131
140
141
146
147
152
155
156
157
159
160
162
164
169
173
181
184
186
187
189
190
191
193
197
217





Barley
0
0
0
0
0
0
45
30
45
15
50
30
35
5
0
20
40
40
5
5
5
5
50
0
5
5


Bermudagrass
90
75
75
85
90
90
95
98
90
90
100
75
95
98
75
98
100
100
80
85
15
100
100
100
100
85


Blackgrass
5
0
0
5
30
40
35
35
5
5
25
10
40
5
5
10
5
35
0
0
0
30
45
15
10
5


Bromegrass, Downy
15
0
5
5
5
5
55
30
10
40
50
5
30
80
40
25
50
50
25
30
5
30
40
30
15
15


Canarygrass
20
0
0
0
0
0
45
35
30
70
90
20
50
85
80
35
80
50
25
35
0
5
50
5
30
20


Chickweed
98
80
10
85
95
90
65
100
98
100
100
95
100
90
100
95
100
100
98
100
100
100
98
98
100
95


Cocklebur
95
98
15
65
25
75
80
55
40
100
100
100
100
100
100
65
100
100
100
100
70
90
98
95
100
98


Corn
60
10
5
45
5
15
45
25
10
80
75
40
75
25
55
25
85
80
10
65
20
0
75
15
35
10


Crabgrass, Large
85
75
65
75
75
75
85
75
55
95
95
90
90
98
95
80
100
100
85
98
75
65
100
90
85
85


Cupgrass, Woolly
85
60
50
65
65
70
98
45
50
85
85
65
100
85
98
95
85
100
75
85
70
80
90
85
85
45


Deadnettle
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
100
98
95
98
98
100
100
100
—


Foxtail, Giant
90
75
75
75
85
80
85
80
80
98
95
75
95
98
98
98
98
100
80
98
75
85
100
85
95
75


Foxtail, Green
90
90
60
75
55
65
75
50
60
85
98
55
98
98
85
70
85
60
80
95
80
40
55
50
30
60



Galium

—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
50
40
50
60
50
40
—
75
—


Goosegrass
85
65
65
75
90
70
85
80
70
95
90
85
70
98
95
90
98
100
95
98
80
75
98
95
98
80


Johnsongrass
60
25
15
15
45
40
90
40
45
100
60
55
98
85
65
80
100
100
70
100
55
65
100
65
85
60



Kochia

85
60
10
65
45
75
65
100
10
0
45
100
45
100
100
65
95
0
85
50
90
10
10
80
80
98


Lambsquarters
100
95
60
80
98
95
95
100
85
98
100
98
95
98
100
98
100
100
98
100
98
98
80
98
100
100


Morningglory
95
70
60
60
15
50
75
85
80
95
65
98
80
95
95
80
100
95
100
95
100
40
65
60
100
75


Nutsedge, Yellow
20
25
45
10
10
60
75
45
60
40
60
75
60
45
20
45
65
40
65
55
40
45
40
65
55
60


Oat, Wild
30
0
5
10
20
10
45
40
35
50
80
30
40
40
30
50
75
80
5
30
10
0
60
50
40
40


Pigweed
98
95
70
75
98
95
98
100
95
75
98
100
100
98
100
90
100
70
100
100
100
75
85
95
90
100


Ragweed
90
85
45
75
80
75
80
70
65
100
90
95
95
98
100
70
100
—
90
98
70
—
—
—
—
80


Ryegrass, Italian
0
0
0
0
5
5
30
30
5
20
40
5
45
5
0
10
40
40
0
0
0
0
40
40
0
30


Soybean
98
95
60
70
85
60
70
95
90
98
95
98
100
95
95
95
100
100
95
100
98
80
95
98
100
85


Surinam Grass
80
60
50
65
65
65
85
55
60
90
75
55
70
95
—
—
80
90
—
85
70
60
85
65
55
80


Velvetleaf
95
85
65
95
85
80
95
100
80
100
100
100
85
70
100
100
100
98
70
95
90
100
80
100
80
98


Wheat
5
0
5
5
0
5
50
30
30
10
55
30
30
15
0
35
45
45
0
0
0
5
40
35
0
45


Windgrass
65
0
5
35
50
50
70
55
50
65
60
30
45
40
30
65
50
80
30
50
40
50
85
70
50
50













62 g ai/ha
31 g ai/ha



Compounds
Compounds




































218
219
220
225
226
227
228
229
233
235
236
237
238
239
240
243
244
245
255
1
2
3
4
7
8
9
10
11





Barley
30
25
10
35
30
5
5
0
0
30
0
15
30
0
5
90
65
85
35
0
10
0
0
0
0
0
0
0


Bermudagrass
80
98
95
85
80
75
85
80
95
98
98
98
98
100
100
98
100
100
95
40
80
15
15
35
60
90
70
80


Blackgrass
0
55
20
5
30
0
35
0
30
60
5
70
60
5
50
80
60
70
5
0
10
0
10
0
5
0
0
5


Bromegrass, Downy
15
50
10
70
0
0
5
15
40
30
5
45
40
5
20
70
50
95
60
0
35
0
10
0
5
5
0
20


Canarygrass
0
55
10
85
30
0
0
15
5
30
0
40
25
0
5
98
95
95
50
0
40
0
10
0
20
5
0
50


Chickweed
100
100
95
40
75
75
100
85
95
100
100
98
90
98
98
100
95
85
98
55
75
90
100
60
98
20
90
80


Cocklebur
—
—
—
100
98
80
98
90
100
—
100
—
—
100
—
—
—
—
—
65
80
65
100
45
100
0
70
90


Corn
10
60
50
50
80
75
85
80
50
100
60
98
80
45
95
95
90
100
75
0
15
0
10
0
15
15
15
70


Crabgrass, Large
45
95
75
85
85
80
98
90
90
98
90
98
98
90
98
100
100
100
85
40
80
60
70
30
70
70
65
80


Cupgrass, Woolly
45
85
60
75
80
75
95
75
85
100
85
100
100
95
100
95
100
100
95
0
75
0
75
0
75
70
60
55


Deadnettle
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Foxtail, Giant
55
70
50
80
90
80
85
80
95
100
80
98
100
85
100
95
95
100
98
0
85
15
80
20
98
75
70
75


Foxtail, Green
85
80
65
98
80
90
90
80
90
90
95
90
95
85
90
98
98
98
90
5
75
5
40
5
40
35
10
60



Galium

—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Goosegrass
10
95
85
90
80
75
80
70
95
98
90
98
98
98
98
95
95
98
90
60
80
15
25
20
80
60
45
65


Johnsongrass
—
60
65
75
85
60
75
100
5
80
15
100
—
20
100
100
95
100
85
0
85
0
45
0
80
60
0
65



Kochia

85
98
65
10
85
75
100
70
85
100
98
80
98
98
98
95
90
100
15
15
60
65
80
0
85
10
10
25


Lambsquarters
98
100
100
85
90
98
98
95
98
100
100
100
100
98
100
100
100
100
95
70
90
85
98
0
95
75
80
50


Morningglory
70
85
65
95
98
100
100
100
80
98
95
95
—
—
—
100
95
100
85
0
70
15
60
15
75
45
0
15


Nutsedge, Yellow
15
55
25
25
65
45
45
20
5
45
15
35
20
30
15
65
50
45
15
15
45
15
55
0
65
20
15
25


Oat, Wild
45
70
20
50
30
0
5
5
35
50
0
55
35
5
40
85
70
85
80
5
30
0
30
0
10
0
0
50


Pigweed
100
100
100
95
85
90
100
95
98
100
85
98
100
98
100
100
100
98
98
65
85
75
100
75
98
80
85
65


Ragweed
95
98
95
80
85
70
80
80
85
100
95
98
100
98
98
95
98
98
90
60
70
80
100
50
90
70
75
100


Ryegrass, Italian
40
25
5
35
0
0
0
0
45
30
0
50
25
0
15
85
60
50
30
0
0
0
10
0
20
0
0
10


Soybean
100
98
85
95
98
65
98
98
98
100
98
100
100
95
95
98
100
98
95
50
80
65
95
60
98
70
95
100


Surinam Grass
80
25
60
75
75
70
85
70
85
90
70
98
100
35
98
95
95
100
80
0
70
15
60
0
60
55
60
60


Velvetleaf
100
90
90
90
85
80
100
75
85
100
100
90
90
100
85
100
100
100
98
55
85
95
70
70
75
85
70
80


Wheat
0
50
0
40
15
0
5
0
30
80
10
70
45
0
35
95
80
95
40
0
5
0
5
0
25
0
0
30


Windgrass
20
40
40
55
50
30
50
40
55
95
50
90
70
30
80
90
70
70
80
0
10
0
50
5
5
50
5
40












31 g ai/ha



Compounds













































12
14
24
26
27
29
33
34
36
37
38
39
40
42
44
45
46
47
48
49
50
51
52
53
55
56
58
59
61
62
63
64
66
67
68
69
70





Barley
0
0
0
0
0
0
0
0
5
0
0
0
0
0
0
5
0
5
5
0
0
5
0
0
0
0
5
0
0
0
0
15
0
0
0
5
10


Bermudagrass
65
70
85
40
70
85
75
75
90
85
98
50
—
70
80
80
80
85
85
75
90
80
85
90
80
75
85
—
75
—
—
95
70
35
75
98
75


Blackgrass
10
0
5
0
0
10
10
0
5
0
5
0
0
5
0
5
0
5
0
0
5
0
5
20
0
0
5
10
0
15
30
0
5
0
0
0
30


Bromegrass, Downy
5
10
25
10
5
5
5
40
30
0
50
0
45
0
40
10
0
35
10
0
0
50
50
35
0
35
40
5
0
30
10
25
5
0
5
40
10


Canarygrass
0
10
40
20
10
10
0
5
40
0
10
0
20
0
20
10
0
20
30
0
0
60
0
40
0
0
60
5
0
0
0
40
0
0
0
0
50


Chickweed
100
—
80
40
40
50
80
50
85
80
85
98
100
60
90
75
80
85
85
75
80
80
95
85
65
90
70
85
80
70
60
98
80
90
85
98
80


Cocklebur
70
80
90
80
90
85
85
0
—
—
—
75
—
0
80
10
75
95
95
65
85
85
75
80
45
5
85
85
0
25
65
90
10
75
25
0
0


Corn
25
10
30
35
35
20
0
0
50
0
55
25
80
0
75
10
20
65
65
5
5
75
30
55
0
45
0
—
0
70
—
80
25
5
0
5
15


Crabgrass, Large
65
50
70
40
50
45
75
80
90
70
90
75
85
70
85
65
60
85
85
75
75
80
85
85
60
75
75
80
65
55
70
85
50
75
75
95
80


Cupgrass, Woolly
55
50
80
40
60
80
65
80
85
55
80
65
90
15
80
70
10
85
80
50
70
75
70
65
10
15
65
75
55
55
50
75
40
60
10
90
45


Deadnettle
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Foxtail, Giant
75
50
70
60
65
80
75
85
95
70
95
75
100
45
95
75
70
90
85
45
75
80
80
80
25
75
75
75
55
55
60
90
65
75
65
95
75


Foxtail, Green
40
45
40
35
80
60
50
70
85
60
85
80
90
50
90
50
45
80
85
50
80
85
95
95
30
80
75
50
50
40
60
70
80
10
40
95
80



Galium

—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Goosegrass
70
80
85
60
90
80
70
75
85
80
80
40
85
70
85
75
75
90
85
65
75
75
75
75
45
65
70
75
40
65
70
80
65
55
65
75
75


Johnsongrass
55
45
60
35
40
20
15
75
65
0
70
65
—
0
70
60
40
85
45
0
0
75
75
55
0
55
50
—
0
0
—
90
45
0
10
98
65



Kochia

20
—
70
—
—
—
10
85
0
0
65
20
0
80
75
0
0
95
98
55
95
20
20
45
20
90
0
—
5
10
10
50
80
75
70
60
65


Lambsquarters
80
85
90
80
90
85
95
95
98
95
90
95
100
90
90
95
80
98
85
70
98
75
85
90
80
98
95
95
85
85
—
95
95
80
95
100
85


Morningglory
15
70
50
50
50
60
60
60
60
60
65
65
70
45
60
75
30
75
70
65
10
75
10
55
55
—
65
—
45
—
—
80
98
80
80
70
98


Nutsedge, Yellow
15
20
20
30
30
40
40
5
10
10
0
0
20
55
40
10
65
65
40
65
70
60
20
20
10
20
25
45
20
15
20
0
25
60
0
5
10


Oat, Wild
0
30
40
40
45
40
10
40
60
0
55
10
85
5
50
35
0
40
40
0
5
60
90
50
0
5
45
30
0
5
0
60
0
0
5
60
55


Pigweed
95
80
70
50
98
60
90
70
85
80
95
98
90
85
75
85
75
98
85
80
80
85
85
85
80
98
80
—
80
98
85
98
98
98
85
98
85


Ragweed
100
80
70
70
85
80
90
75
90
80
75
85
98
70
85
80
70
85
85
75
80
80
75
80
70
55
80
75
75
70
70
85
0
75
75
90
60


Ryegrass, Italian
0
0
0
0
0
5
5
10
0
0
35
0
0
0
5
30
0
0
0
0
0
0
40
0
0
0
0
5
0
0
0
0
0
0
5
30
10


Soybean
98
80
85
95
95
85
95
85
90
75
85
95
100
70
95
80
75
95
95
55
85
85
80
90
25
85
85
90
0
75
75
85
95
80
80
80
75


Surinam Grass
25
40
50
30
50
50
45
70
75
60
70
60
85
40
85
70
45
85
70
15
65
80
75
85
10
75
70
75
20
20
10
85
65
10
25
85
65


Velvetleaf
80
85
75
70
50
50
80
80
98
75
95
75
98
80
95
70
75
80
85
90
90
80
95
85
90
85
75
85
80
85
95
85
85
90
95
95
75


Wheat
0
0
5
0
0
0
0
0
5
0
0
5
0
0
5
10
0
0
0
0
0
5
15
20
0
0
0
0
0
0
0
10
0
5
5
5
5


Windgrass
10
5
20
10
10
5
10
10
50
5
70
0
70
10
65
30
10
60
70
0
10
50
60
60
0
30
35
20
0
30
10
70
60
0
40
60
80












31 g ai/ha



Compounds






































71
72
73
74
75
77
79
80
81
82
83
85
86
87
88
89
90
91
92
93
94
95
96
97
98
99
100
102
107
108





Barley
0
0
0
0
0
0
5
15
0
0
0
5
30
0
30
0
0
0
0
0
0
0
0
0
0
5
5
0
0
0


Bermudagrass
65
75
65
75
90
90
80
20
85
80
75
85
85
90
80
75
70
75
20
60
80
45
80
95
75
75
70
80
75
85


Blackgrass
0
0
0
0
0
0
5
0
5
0
0
5
15
5
0
10
5
10
0
0
5
0
5
5
0
0
0
0
0
0


Bromegrass, Downy
0
0
20
0
5
0
5
45
5
0
40
0
10
20
40
0
5
0
0
0
0
0
0
0
5
5
5
0
0
0


Canarygrass
0
0
0
0
0
0
15
45
0
0
20
35
20
0
60
10
5
25
0
0
0
0
0
0
5
40
0
5
5
0


Chickweed
75
70
80
75
85
80
80
90
95
90
90
85
80
100
75
75
70
85
90
80
95
75
75
95
80
80
75
60
98
85


Cocklebur
65
75
0
20
40
0
95
0
5
85
75
95
85
98
90
10
75
20
25
70
45
70
75
95
98
95
40
90
98
75


Corn
0
0
20
0
0
0
5
5
5
0
0
50
10
20
15
80
15
25
20
0
0
0
45
20
35
40
0
—
65
15


Crabgrass, Large
65
75
80
80
95
55
80
75
85
70
85
90
85
85
95
85
65
80
80
70
70
45
75
75
75
85
55
70
75
60


Cupgrass, Woolly
10
45
60
10
10
20
10
65
65
55
70
75
75
50
75
35
45
70
10
45
—
45
70
55
65
70
—
70
65
40


Deadnettle
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Foxtail, Giant
20
65
70
25
75
65
70
75
75
75
80
75
90
75
95
70
65
85
65
70
65
45
65
60
65
75
70
70
75
45


Foxtail, Green
60
10
70
20
65
40
60
90
5
60
90
80
70
75
95
60
65
70
75
50
10
20
50
40
30
50
20
80
70
5



Galium

—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Goosegrass
75
60
65
65
75
65
45
70
65
75
75
70
70
75
65
55
60
30
60
60
45
65
70
60
60
75
70
55
75
60


Johnsongrass
65
0
10
0
0
0
0
0
5
65
95
80
95
5
95
25
10
65
20
10
—
5
20
15
55
70
0
20
60
10



Kochia

0
75
75
75
75
75
75
0
75
10
65
75
75
100
75
65
65
20
75
65
—
80
65
65
65
80
—
65
98
70


Lambsquarters
75
90
85
95
98
95
95
95
95
80
95
98
100
98
95
95
85
85
90
85
80
80
90
90
95
98
95
95
90
98


Morningglory
65
20
0
60
20
75
80
85
75
65
70
95
70
45
90
70
65
75
80
70
55
100
65
100
70
100
60
65
100
75


Nutsedge, Yellow
10
35
20
20
10
45
25
10
65
10
10
75
65
10
25
35
60
50
45
45
20
75
70
75
50
45
—
45
75
50


Oat, Wild
0
0
55
20
0
0
40
20
25
0
10
5
20
50
50
10
0
30
0
0
0
0
0
0
10
10
0
5
0
0


Pigweed
85
80
80
90
100
98
100
100
98
75
80
100
98
98
98
80
85
100
90
90
100
85
90
95
100
100
90
70
95
95


Ragweed
75
75
75
75
80
75
80
50
75
75
75
80
80
85
75
70
60
85
40
65
40
75
80
85
70
65
70
70
75
80


Ryegrass, Italian
0
0
35
5
0
0
20
0
0
0
0
0
25
5
5
0
0
0
0
0
0
0
0
0
0
0
5
0
0
0


Soybean
65
80
80
75
80
25
75
75
85
75
75
80
80
98
75
90
98
75
90
55
65
95
65
70
90
98
95
75
95
45


Surinam Grass
50
75
80
20
50
65
20
45
75
65
75
75
80
75
95
55
65
85
25
50
—
45
75
65
65
70
—
60
75
55


Velvetleaf
75
98
95
98
100
90
95
85
100
85
85
90
98
100
80
90
85
98
95
85
—
85
95
100
95
95
—
98
90
100


Wheat
0
0
0
5
0
0
10
5
5
0
0
0
5
35
0
0
5
0
0
0
0
0
0
0
0
0
0
0
0
0


Windgrass
5
5
70
5
30
10
50
50
10
5
5
40
30
55
40
0
0
10
0
5
0
0
5
5
0
5
0
5
5
0












31 g ai/ha



Compounds


































109
111
113
117
118
119
120
121
122
123
126
127
128
129
130
131
140
141
146
147
152
155
156
157
159
160





Barley
0
0
0
0
0
0
—
0
0
5
5
0
0
0
0
0
0
0
0
0
10
30
30
5
20
5


Bermudagrass
70
95
80
75
75
75
80
95
75
80
75
95
75
80
75
65
60
80
85
75
95
85
80
75
95
65


Blackgrass
0
5
0
0
5
5
30
5
5
20
5
5
5
0
0
0
0
5
5
10
20
10
5
0
20
5


Bromegrass, Downy
0
0
5
5
0
10
20
25
5
0
5
5
30
5
10
0
0
0
0
0
30
5
10
40
50
0


Canarygrass
0
0
65
0
0
5
0
0
10
25
15
5
10
0
5
0
0
0
0
0
35
10
15
40
80
5


Chickweed
90
95
98
85
90
70
60
100
70
70
65
65
90
85
98
65
0
60
70
70
10
100
80
100
100
85


Cocklebur
75
98
95
75
40
0
10
40
20
65
15
75
98
95
85
95
0
40
10
50
70
15
20
100
95
98


Corn
0
10
25
10
0
20
15
25
0
35
10
5
40
20
55
0
0
0
0
0
25
5
10
70
60
15


Crabgrass, Large
65
70
85
75
70
75
80
85
75
70
75
80
85
80
85
75
50
70
65
60
75
60
45
80
80
80


Cupgrass, Woolly
—
40
85
65
65
75
70
95
65
25
65
75
85
80
80
50
50
65
60
65
95
20
40
85
70
65


Deadnettle
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Foxtail, Giant
70
60
80
65
75
75
75
95
70
65
70
80
95
70
90
75
65
75
75
65
80
65
75
98
85
70


Foxtail, Green
20
40
80
50
50
85
90
80
80
50
50
75
85
80
90
70
45
50
50
40
75
25
45
70
85
55



Galium

—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Goosegrass
65
70
70
45
55
75
75
95
40
65
65
65
90
85
85
65
45
65
75
35
80
65
65
85
85
80


Johnsongrass
5
10
65
5
10
10
15
20
45
35
65
65
70
40
60
5
10
15
45
15
70
10
15
70
45
45



Kochia

70
80
98
45
45
40
10
95
0
60
10
45
60
80
85
35
0
20
40
40
10
35
10
0
40
90


Lambsquarters
98
98
95
95
85
85
80
95
60
80
70
75
95
90
98
85
45
80
95
85
85
98
80
98
100
95


Morningglory
70
100
98
10
10
10
15
5
60
70
75
65
80
90
95
70
0
60
0
50
45
55
80
20
60
75


Nutsedge, Yellow
—
65
65
0
35
10
5
5
55
65
65
65
20
35
10
15
10
0
5
50
65
20
45
30
40
65


Oat, Wild
0
0
20
5
5
50
50
60
5
0
5
5
40
0
20
0
0
10
0
5
30
10
5
30
60
10


Pigweed
100
95
95
95
85
95
95
100
85
80
75
80
95
85
95
90
55
60
95
85
95
98
60
65
95
90


Ragweed
75
75
80
70
70
70
50
65
60
70
55
70
85
90
85
80
25
65
65
20
60
45
65
90
90
80


Ryegrass, Italian
0
0
40
0
5
5
10
40
5
0
0
0
0
0
0
0
0
0
5
5
5
5
0
10
30
0


Soybean
95
70
98
65
75
0
40
90
45
60
70
95
98
95
98
75
10
70
70
15
70
95
80
95
95
85


Surinam Grass
65
60
85
65
50
75
20
95
75
25
70
75
50
80
80
20
50
40
65
50
75
40
40
75
75
40


Velvetleaf
90
80
85
70
75
75
75
98
80
80
80
90
90
95
95
80
50
75
80
60
85
100
60
100
100
90


Wheat
0
0
0
0
0
10
20
5
15
10
5
5
0
0
5
0
5
0
0
0
35
15
15
0
40
10


Windgrass
30
0
5
40
50
60
60
80
5
30
10
25
50
45
60
0
0
25
45
10
50
50
40
60
45
20












31 g ai/ha



Compounds


































162
164
169
173
181
184
186
187
189
190
191
193
197
217
218
219
220
225
226
227
228
229
233
235
236
237





Barley
30
5
0
5
5
5
0
0
0
0
5
0
0
0
30
0
10
20
10
0
0
0
0
0
0
5


Bermudagrass
85
70
70
98
100
98
80
75
10
98
100
95
95
70
70
95
80
80
80
75
80
75
95
98
95
98


Blackgrass
30
5
5
5
0
30
0
0
0
5
30
10
0
0
0
50
10
0
5
0
5
0
5
45
0
50


Bromegrass, Downy
20
40
10
5
40
40
5
5
0
5
35
10
15
10
5
45
10
35
0
0
5
5
40
10
0
30


Canarygrass
40
40
40
10
50
45
5
10
0
0
20
5
5
0
0
35
10
60
5
0
0
5
0
20
0
30


Chickweed
90
80
100
65
100
100
95
100
98
—
98
95
100
75
100
100
95
25
75
65
98
70
90
98
75
90


Cocklebur
100
98
100
60
100
100
90
100
60
40
90
95
80
80
—
—
—
98
98
75
98
85
90
—
—
—


Corn
50
15
45
5
70
80
10
50
20
0
65
0
15
0
0
10
25
40
75
20
80
70
30
95
15
85


Crabgrass, Large
80
95
85
70
98
100
80
85
75
60
85
75
75
80
40
90
70
75
85
80
80
80
80
98
75
95


Cupgrass, Woolly
90
75
85
85
80
75
70
80
70
75
85
75
70
25
40
85
60
75
80
55
75
70
80
95
70
100


Deadnettle
—
—
—
—
—
100
90
80
85
65
90
100
100
—
—
—
—
—
—
—
—
—
—
—
—
—


Foxtail, Giant
85
90
95
95
98
98
75
98
75
70
100
75
85
70
40
70
30
75
85
75
85
75
90
98
75
98


Foxtail, Green
98
70
60
55
70
30
50
65
65
25
40
40
5
55
60
70
60
85
70
50
85
40
85
90
80
80



Galium

—
—
—
—
—
50
40
20
20
50
20
75
75
—
—
—
—
—
—
—
—
—
—
—
—
—


Goosegrass
60
85
95
80
95
100
85
85
60
70
95
85
85
80
0
90
80
85
80
75
80
70
85
95
80
95


Johnsongrass
98
45
60
65
100
100
65
90
50
60
70
50
70
0
—
—
60
60
85
45
75
70
0
70
0
100



Kochia

20
98
100
65
65
0
75
40
85
0
5
20
65
75
35
80
45
5
80
70
90
55
70
98
80
65


Lambsquarters
80
98
100
98
100
80
98
98
98
80
75
98
95
90
98
100
100
85
90
90
98
85
98
98
98
95


Morningglory
75
90
95
75
95
40
95
80
100
40
40
40
98
70
70
60
65
95
98
100
100
98
65
95
60
85


Nutsedge, Yellow
25
40
0
45
60
35
65
45
20
35
40
60
45
10
10
10
10
10
55
10
40
0
0
45
0
20


Oat, Wild
35
25
0
50
65
40
0
10
5
0
50
0
40
30
40
50
10
45
25
0
0
0
30
35
0
40


Pigweed
100
98
100
85
100
70
85
100
80
65
80
90
80
85
100
100
95
90
75
80
98
80
85
100
85
80


Ragweed
90
85
100
55
98
—
85
95
10
—
—
—
—
80
95
80
90
75
80
60
70
80
80
98
80
95


Ryegrass, Italian
40
5
0
0
10
20
0
0
0
0
40
5
0
0
30
20
5
0
0
0
0
0
30
30
0
50


Soybean
98
80
90
60
100
98
85
98
90
80
90
80
98
75
85
95
80
85
95
55
95
95
98
98
90
95


Surinam Grass
65
60
—
—
70
80
—
65
65
60
70
65
50
70
75
10
50
75
75
55
75
65
80
80
60
85


Velvetleaf
80
70
100
100
100
85
70
90
85
100
75
90
80
98
85
85
80
80
85
80
80
75
80
95
98
85


Wheat
10
0
0
10
40
30
0
0
0
0
35
30
0
30
0
40
0
30
10
0
0
0
10
45
0
50


Windgrass
40
5
15
30
40
60
10
10
25
15
55
50
10
50
10
35
5
50
10
0
5
0
50
85
30
60














31 g ai/ha




Compounds

















238
239
240
243
244
245
255







Barley
10
0
5
60
50
45
30



Bermudagrass
95
95
98
98
80
80
90



Blackgrass
40
5
40
60
50
40
5



Bromegrass, Downy
10
0
10
50
40
60
50



Canarygrass
20
0
5
90
80
80
50



Chickweed
80
90
90
80
80
80
95



Cocklebur
—
90
—
—
—
—
—



Corn
80
5
90
90
85
100
60



Crabgrass, Large
95
75
80
95
80
80
85



Cupgrass, Woolly
95
75
98
95
100
100
85



Deadnettle
—
—
—
—
—
—
—



Foxtail, Giant
100
75
100
95
95
98
95



Foxtail, Green
85
80
90
98
85
85
85




Galium

—
—
—
—
—
—
—



Goosegrass
95
80
95
95
85
98
90



Johnsongrass
60
0
—
100
85
100
80




Kochia

90
90
80
85
85
85
10



Lambsquarters
100
98
98
100
100
98
90



Morningglory
—
95
—
95
90
90
75



Nutsedge, Yellow
20
30
10
65
45
40
10



Oat, Wild
30
0
25
80
50
70
65



Pigweed
100
95
—
85
95
80
80



Ragweed
100
95
98
90
98
95
50



Ryegrass, Italian
20
0
10
60
35
40
10



Soybean
98
70
95
95
85
95
95



Surinam Grass
95
25
95
90
90
100
80



Velvetleaf
80
100
75
100
100
100
95



Wheat
40
0
30
85
60
75
35



Windgrass
45
20
60
80
50
65
50














16 g ai/ha
8 g ai/ha



Compounds
Compound
















2
69
122
131
159
169
225
159





Barley
0
0
0
0
20
0
5
0


Bermudagrass
40
85
65
60
80
70
40
70


Blackgrass
0
0
0
0
5
0
0
0


Bromegrass, Downy
20
30
5
0
15
0
30
15


Canarygrass
20
0
0
0
40
5
55
25


Chickweed
70
95
65
45
100
90
15
80


Cocklebur
75
0
0
80
80
100
85
75


Corn
15
0
0
0
25
20
10
15


Crabgrass, Large
70
95
65
65
75
75
70
65


Cupgrass, Woolly
75
75
65
10
65
75
70
60


Foxtail, Giant
70
80
65
65
80
75
75
75


Foxtail, Green
50
75
40
40
80
45
85
50


Goosegrass
80
75
10
65
80
80
80
70


Johnsongrass
75
75
20
0
45
40
20
10



Kochia

55
60
0
20
20
100
5
20


Lambsquarters
80
100
55
75
95
95
85
90


Morningglory
55
65
55
5
10
95
80
0


Nutsedge, Yellow
40
5
35
0
20
0
5
10


Oat, Wild
5
50
5
0
35
0
25
0


Pigweed
70
95
75
60
75
90
80
55


Ragweed
65
75
55
65
80
98
70
65


Ryegrass, Italian
0
0
5
0
0
0
0
0


Soybean
75
45
20
75
85
55
65
80


Surinam Grass
70
75
25
15
65
—
35
65


Velvetleaf
—
75
75
70
100
75
80
98


Wheat
0
0
5
0
35
0
20
10


Windgrass
10
40
5
0
40
5
5
10










Preemergence









250 g ai/ha



Compounds


































3
7
9
10
11
12
14
24
26
27
29
33
34
36
37
38
39
40
42
44
45
46
47
48
49
50





Bermudagrass
90
98
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
98
100
100
100
100


Blackgrass
0
0
40
20
60
10
0
10
10
30
50
30
50
25
10
40
0
5
5
60
5
0
5
5
0
5


Bromegrass, Downy
0
0
10
0
5
0
0
20
10
30
5
30
80
10
0
40
0
10
0
5
5
0
10
45
—
0


Cocklebur
100
75
100
98
100
100
95
95
98
90
90
90
85
80
45
90
45
100
—
45
—
15
—
85
55
—


Corn
5
0
10
0
35
75
10
5
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Crabgrass, Large
100
95
100
95
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
98
100
100
100
100


Cupgrass, Woolly
10
45
60
40
75
85
70
90
85
80
90
85
100
65
70
80
10
85
5
85
75
60
90
95
20
70


Foxtail, Giant
0
25
98
45
100
100
90
100
90
95
100
98
100
80
75
95
75
98
10
98
75
25
100
98
45
90


Foxtail, Green
0
0
—
30
65
80
60
100
70
80
100
100
100
85
90
100
100
100
85
100
100
10
98
98
30
100



Galium

50
0
95
85
75
95
80
80
98
95
100
90
98
95
100
85
85
90
50
98
85
70
95
70
95
98


Goosegrass
98
60
100
98
100
100
100
100
100
100
100
98
100
100
100
100
100
100
100
100
100
98
100
100
100
100


Johnsongrass
10
0
98
75
98
98
95
90
90
85
90
20
100
85
90
95
75
90
65
95
85
70
100
98
10
95



Kochia

100
100
100
100
100
100
100
100
100
100
100
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Lambsquarters
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
98
100


Morningglory
100
20
98
40
100
100
100
100
100
100
100
90
98
20
0
100
100
65
0
95
0
0
55
100
85
55


Nightshade
100
100
100
100
100
100
100
100
100
100
100
100
100
98
85
100
100
100
100
100
100
98
100
100
98
100


Nutsedge, Yellow
50
55
95
75
90
90
85
90
85
90
85
90
90
75
90
80
10
85
85
90
70
90
90
90
90
90


Oat, Wild
0
0
60
10
40
5
0
80
5
50
50
50
60
0
10
20
0
30
0
30
5
0
10
15
0
0


Pigweed
95
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100


Ragweed
90
90
100
100
100
100
90
100
100
100
100
100
90
90
98
95
95
95
80
95
95
100
95
95
95
100


Russian Thistle
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Ryegrass, Italian
0
0
40
0
0
0
0
10
0
0
40
5
10
0
0
40
0
5
0
0
0
0
0
0
5
0


Soybean
50
30
80
75
95
95
85
85
90
90
95
75
80
40
35
75
0
70
0
0
0
25
0
20
85
0


Sunflower
85
25
98
98
98
100
98
98
95
100
100
90
90
85
90
75
65
80
75
80
75
60
85
80
75
85


Surinam Grass
5
10
95
80
75
100
80
100
90
95
95
100
90
100
100
80
15
90
75
100
98
90
100
100
85
100


Velvetleaf
100
100
100
100
100
100
100
100
100
95
100
100
100
100
98
100
98
100
90
100
95
65
100
100
100
100


Wheat
0
0
5
5
5
0
0
0
0
5
0
5
0
0
0
5
0
—
0
0
0
0
0
0
0
0












250 g ai/ha



Compounds


































51
52
53
55
56
58
59
61
62
63
64
66
67
68
72
73
74
75
77
81
113
119
120
193
217
218





Bermudagrass
100
100
100
100
100
100
98
98
100
98
98
98
100
100
100
100
100
100
100
100
100
100
100
98
100
100


Blackgrass
20
10
60
30
5
30
40
0
0
40
0
5
5
5
5
10
10
10
0
35
20
70
50
70
0
20


Bromegrass, Downy
40
5
30
0
5
0
0
0
0
0
0
0
0
5
0
20
0
0
0
0
10
55
85
50
0
0


Cocklebur
75
75
70
15
0
65
75
65
10
10
70
0
20
80
80
65
80
90
65
85
100
85
98
95
85
100


Corn
0
0
20
0
0
0
0
0
—
0
0
0
0
0
0
10
0
0
0
55
0
50
55
5
0
0


Crabgrass, Large
100
100
100
98
98
100
98
98
98
100
98
100
100
100
100
100
100
100
100
100
100
100
100
100
100
98


Cupgrass, Woolly
85
80
95
55
70
85
85
0
10
10
10
75
10
85
65
80
5
75
0
85
95
100
90
90
80
85


Foxtail, Giant
75
75
100
10
80
75
75
45
20
10
65
80
65
75
65
80
45
80
45
98
85
100
100
80
85
85


Foxtail, Green
100
100
98
0
100
100
98
75
10
30
50
75
40
85
90
80
0
98
15
100
100
100
100
98
90
100



Galium

95
95
90
85
85
80
98
98
0
20
70
0
90
85
85
85
98
98
90
100
95
100
98
100
90
100


Goosegrass
100
100
100
98
100
100
100
98
98
100
100
98
98
98
100
100
100
100
98
100
100
100
100
100
100
98


Johnsongrass
80
95
75
0
80
85
90
20
—
60
75
98
0
95
10
98
0
70
0
90
70
95
90
60
55
45



Kochia

—
—
—
—
—
—
98
—
100
100
95
85
85
95
85
90
85
95
95
70
90
98
75
90
—
—


Lambsquarters
98
100
100
100
98
98
100
—
100
100
98
100
98
100
100
100
100
100
100
98
100
100
100
100
100
100


Morningglory
70
55
65
65
65
75
60
65
20
55
0
80
80
85
75
70
80
90
90
95
—
95
100
95
0
65


Nightshade
100
100
100
100
100
100
100
—
98
98
98
98
98
100
100
100
100
100
100
100
100
100
98
100
100
100


Nutsedge, Yellow
90
90
90
65
90
90
90
90
—
90
10
95
75
90
90
85
90
90
90
95
90
98
98
90
90
90


Oat, Wild
0
60
70
0
0
30
0
0
0
0
5
40
0
5
0
65
5
0
0
0
40
80
65
60
0
0


Pigweed
100
100
100
100
100
100
100
—
100
100
98
98
98
100
100
100
100
100
100
100
100
100
100
100
100
100


Ragweed
90
95
90
90
80
90
95
90
60
85
85
55
50
90
85
85
100
95
95
90
98
95
95
100
95
100


Russian Thistle
—
—
—
—
—
—
—
—
—
—
—
—
90
98
80
—
98
—
—
100
—
100
—
100
—
—


Ryegrass, Italian
5
0
50
0
0
0
20
5
20
0
0
5
0
0
0
5
0
0
0
0
40
100
100
45
10
5


Soybean
85
80
85
65
90
95
80
20
—
15
—
—
—
—
—
—
—
—
—
—
90
80
80
80
0
90


Sunflower
75
75
65
70
75
75
80
70
55
70
55
10
55
85
80
75
85
85
85
90
95
85
95
95
85
95


Surinam Grass
100
98
100
45
98
95
95
35
60
85
90
100
75
85
98
100
95
75
100
100
98
100
100
45
90
100


Velvetleaf
100
100
100
100
98
95
100
100
95
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100


Wheat
10
0
10
0
10
0
0
0
0
0
0
0
0
0
0
30
0
0
0
0
10
50
30
25
0
0













250 g ai/ha
125 g ai/ha



Compounds
Compounds


































219
220
243
244
245
255
2
3
7
9
10
11
12
14
24
26
27
29
33
34
36
37
38
39
40
42





Bermudagrass
100
100
100
100
100
100
100
80
85
100
100
100
100
100
100
98
100
100
100
100
100
98
100
100
100
100


Blackgrass
60
35
95
70
45
60
50
0
0
20
0
30
5
0
0
0
10
50
10
50
25
5
30
0
0
0


Bromegrass, Downy
20
5
70
30
15
40
5
0
0
5
0
0
0
0
0
0
0
0
5
10
0
0
5
0
5
0


Cocklebur
85
0
98
100
100
—
80
70
0
65
65
95
98
85
95
85
85
90
85
75
—
0
25
—
85
—


Corn
0
0
95
85
65
0
0
0
0
0
0
0
15
0
0
0
0
0
0
0
0
0
0
0
0
0


Crabgrass, Large
100
100
100
100
100
100
100
85
45
100
70
100
100
100
100
100
100
100
100
100
100
10
100
100
100
95


Cupgrass, Woolly
80
25
100
100
100
90
20
0
0
45
35
15
75
50
85
50
60
55
60
100
10
10
60
0
70
0


Foxtail, Giant
80
75
95
100
100
98
70
0
0
60
0
75
70
75
90
45
85
100
95
90
65
0
80
70
80
10


Foxtail, Green
100
100
100
90
100
100
60
0
0
5
0
65
40
10
100
30
50
100
100
90
85
0
85
75
85
85



Galium

100
100
100
98
95
100
—
30
0
60
85
50
90
40
10
90
85
98
50
90
80
30
85
85
85
10


Goosegrass
100
100
100
100
100
100
100
85
45
100
95
100
100
98
100
95
100
100
90
100
95
80
100
100
100
100


Johnsongrass
80
80
100
100
100
98
80
0
0
90
60
85
75
80
90
60
50
30
0
98
80
45
85
65
85
10



Kochia

—
—
100
100
100
—
100
100
100
100
100
100
100
100
100
100
100
100
—
—
—
—
—
—
—
—


Lambsquarters
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100


Morningglory
100
90
100
100
100
90
75
100
0
70
0
35
85
100
100
100
100
100
70
75
0
0
0
15
0
0


Nightshade
100
100
98
100
100
100
100
98
95
100
100
100
100
100
100
100
100
100
100
100
95
80
98
100
98
100


Nutsedge, Yellow
90
90
95
95
80
90
70
40
15
80
55
85
75
40
85
50
30
60
70
75
40
20
70
0
65
75


Oat, Wild
40
60
90
40
30
90
50
0
0
0
0
10
0
0
0
0
30
45
30
30
0
0
0
0
0
0


Pigweed
100
100
100
100
100
100
100
90
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100


Ragweed
98
95
98
100
100
100
98
90
15
100
100
100
100
90
98
95
100
100
100
90
85
65
80
75
90
25


Russian Thistle
—
—
100
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Ryegrass, Italian
10
0
70
45
40
30
5
0
0
0
0
0
0
0
10
0
0
10
5
5
0
0
5
0
5
0


Soybean
75
75
95
95
75
80
70
35
20
—
65
65
80
50
80
80
80
90
65
65
0
0
0
0
20
0


Sunflower
85
90
95
100
95
90
90
70
0
95
95
95
98
85
95
90
90
90
75
80
55
45
25
25
75
55


Surinam Grass
100
65
100
100
100
100
60
0
0
95
15
35
95
60
95
90
60
90
95
65
100
55
65
10
85
10


Velvetleaf
95
100
100
100
100
100
100
90
100
100
100
100
100
100
100
100
90
100
100
95
100
20
98
75
100
85


Wheat
0
5
70
45
15
5
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0












125 g ai/ha



Compounds



































44
45
46
47
48
49
50
51
52
53
55
56
58
59
61
62
63
64
66
67
68
69
72
73
74
75
77





Bermudagrass
100
100
—
100
100
98
100
100
98
100
100
100
100
98
75
95
98
98
98
95
98
100
98
98
100
100
100


Blackgrass
40
0
0
5
0
0
0
10
0
5
0
0
5
30
0
0
5
0
5
0
0
0
0
0
0
5
0


Bromegrass, Downy
0
0
0
5
0
0
0
5
5
5
0
0
0
0
0
0
0
0
0
0
0
0
0
5
0
0
0


Cocklebur
—
—
0
—
0
45
75
20
10
65
10
0
10
10
20
0
0
10
0
15
—
10
70
60
70
75
10


Corn
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Crabgrass, Large
100
100
85
100
100
98
100
100
100
100
95
98
98
98
98
80
100
98
95
98
98
100
100
100
100
100
98


Cupgrass, Woolly
80
60
50
75
75
0
15
75
65
85
0
50
20
65
0
5
0
0
60
0
55
45
45
55
0
55
0


Foxtail, Giant
75
45
15
85
85
20
90
50
25
100
0
75
75
60
15
20
0
35
75
45
55
90
10
75
5
80
5


Foxtail, Green
98
80
5
98
98
5
95
98
45
98
0
20
70
90
40
10
—
0
30
—
25
85
50
30
0
50
0



Galium

65
50
0
50
60
90
95
80
70
0
20
60
30
95
98
0
0
30
0
85
70
0
85
80
40
95
85


Goosegrass
100
100
98
100
100
98
100
100
100
100
98
95
100
100
98
98
100
98
90
90
98
100
100
100
100
100
98


Johnsongrass
90
75
45
80
90
0
90
75
90
60
0
55
80
80
10
0
55
55
85
0
75
85
0
98
0
65
0



Kochia

—
—
—
—
—
—
—
—
—
—
—
—
—
60
85
100
100
45
85
80
95
45
85
80
85
90
90


Lambsquarters
100
100
95
100
100
98
100
98
100
100
98
98
98
100
98
100
100
98
98
98
98
100
98
100
98
100
100


Morningglory
50
—
0
0
100
80
—
20
45
25
45
45
55
55
45
0
0
0
25
15
65
0
65
45
75
75
75


Nightshade
100
100
98
100
100
98
100
98
98
100
100
98
98
100
98
98
98
95
98
95
100
98
98
98
98
98
98


Nutsedge, Yellow
75
20
80
80
85
85
90
85
80
90
45
85
75
85
90
45
25
0
85
65
85
0
75
65
65
90
90


Oat, Wild
5
0
0
0
0
0
0
0
5
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
5
0
0


Pigweed
100
100
95
100
100
100
100
100
100
100
98
100
100
100
100
100
100
85
98
98
100
100
100
100
100
100
100


Ragweed
95
80
100
90
90
80
95
80
85
85
85
70
85
90
75
45
70
75
45
35
80
65
80
75
98
95
90


Russian Thistle
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
80
100
80
—
90
—
—


Ryegrass, Italian
0
0
0
0
0
0
0
0
0
0
0
0
0
20
5
0
0
0
0
0
0
0
0
0
0
0
0


Soybean
0
0
15
0
0
85
—
80
55
80
15
80
85
0
0
80
5
—
—
—
—
—
—
—
—
—
—


Sunflower
75
10
0
80
80
75
85
75
70
65
60
65
65
70
60
10
20
0
0
35
75
5
65
70
70
75
75


Surinam Grass
90
98
75
100
100
75
98
98
95
100
0
98
85
85
0
25
55
85
90
15
55
100
75
100
85
60
75


Velvetleaf
100
85
55
90
100
100
100
98
98
98
100
98
95
100
98
95
100
95
95
90
100
85
100
100
100
100
100


Wheat
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
5
0
0
0













125 g ai/ha
62 g ai/ha



Compounds
Compounds


































81
113
119
120
193
217
218
219
220
243
244
245
255
2
3
7
9
10
11
12
14
24
26
27
29
33





Bermudagrass
100
100
100
100
95
100
100
100
98
100
100
100
100
100
70
0
100
80
100
100
75
100
70
98
100
100


Blackgrass
35
0
50
50
30
0
0
40
20
70
60
30
40
0
0
0
0
0
5
0
0
0
0
0
5
0


Bromegrass, Downy
0
10
55
30
5
0
0
10
0
60
5
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Cocklebur
75
90
70
60
—
85
90
—
—
95
100
98
—
65
10
0
25
15
75
80
85
—
40
85
80
80


Corn
50
0
50
25
5
0
0
0
0
85
60
25
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Crabgrass, Large
100
100
100
100
100
100
65
100
80
100
100
100
100
100
70
0
90
0
100
90
50
98
40
80
100
98


Cupgrass, Woolly
75
85
95
75
80
65
65
20
10
95
95
80
75
15
0
0
15
10
0
10
5
70
5
0
10
50


Foxtail, Giant
85
60
95
98
70
75
20
10
0
95
100
90
55
20
0
0
15
0
35
20
10
85
10
5
50
45


Foxtail, Green
100
60
100
100
50
0
80
90
—
100
90
75
80
5
0
0
0
0
25
0
0
40
0
30
40
45



Galium

100
85
90
95
100
70
95
98
90
98
98
95
60
—
5
0
40
10
50
50
0
0
50
50
80
10


Goosegrass
100
100
100
100
100
100
98
100
98
100
100
100
100
100
70
25
98
75
95
95
85
98
80
98
100
85


Johnsongrass
90
60
95
80
15
20
20
65
0
95
100
80
75
65
0
0
85
10
55
0
30
85
10
5
5
0



Kochia

65
85
55
50
80
—
—
—
—
90
95
98
—
100
—
100
100
50
100
100
100
100
100
100
100
—


Lambsquarters
98
100
100
100
100
100
100
100
100
100
100
100
100
100
—
100
100
100
100
100
100
100
100
100
100
100


Morningglory
80
—
95
90
95
0
15
15
0
98
98
65
65
20
100
0
40
0
0
55
100
100
100
100
100
15


Nightshade
98
100
98
95
100
100
100
100
98
98
100
100
100
100
—
90
100
100
100
100
98
98
100
98
90
100


Nutsedge, Yellow
95
90
98
98
70
70
90
85
60
90
80
65
40
40
10
10
45
0
55
60
30
50
50
20
30
45


Oat, Wild
0
20
50
65
30
0
0
5
0
85
10
30
60
5
0
0
0
0
0
0
0
0
0
0
0
0


Pigweed
100
100
100
100
100
100
100
100
100
100
100
100
100
100
—
100
100
100
100
100
98
100
100
100
100
100


Ragweed
90
95
95
95
100
90
98
85
80
98
100
100
85
85
65
0
90
100
100
98
90
90
85
85
90
85


Russian Thistle
100
—
100
80
100
—
—
—
—
100
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Ryegrass, Italian
0
5
100
100
25
5
5
5
0
45
5
0
10
0
0
0
0
0
0
0
0
0
0
0
0
0


Soybean
—
85
80
80
60
0
80
65
0
85
90
55
15
60
30
0
10
60
45
65
—
60
60
70
85
60


Sunflower
85
90
70
85
80
85
90
80
70
95
85
80
75
70
70
0
85
80
85
98
85
90
90
75
85
75


Surinam Grass
100
95
100
100
30
85
98
45
45
100
100
100
95
20
0
0
45
10
25
60
5
75
5
20
20
65


Velvetleaf
100
100
100
100
100
100
90
90
90
100
100
100
98
90
90
85
100
100
100
100
98
100
90
85
90
90


Wheat
0
10
30
25
10
0
0
0
0
70
5
5
0
0
0
0
0
—
0
0
0
0
0
0
0
0












62 g ai/ha



Compounds



































34
36
37
38
39
40
42
44
45
46
47
48
49
50
51
52
53
55
56
58
59
61
62
63
64
66
67





Bermudagrass
100
100
80
100
100
100
100
100
100
—
100
100
—
100
98
98
100
98
100
98
98
75
75
98
85
80
90


Blackgrass
5
25
0
5
0
0
0
30
0
0
5
0
0
0
0
0
5
0
0
0
0
0
0
0
0
0
0


Bromegrass, Downy
0
0
0
0
0
0
0
0
0
0
5
0
0
0
0
5
0
0
0
0
0
0
0
0
0
0
0


Cocklebur
55
—
—
10
—
—
0
—
—
0
0
0
20
75
0
0
20
10
0
0
0
10
0
0
0
0
0


Corn
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
—
0
0
0
0


Crabgrass, Large
100
90
0
90
95
98
85
75
95
75
95
90
95
100
98
98
100
60
85
98
95
85
50
85
75
85
65


Cupgrass, Woolly
100
0
0
10
0
50
0
45
45
45
45
10
0
5
35
10
55
0
20
10
65
0
0
0
0
40
0


Foxtail, Giant
55
20
0
40
45
65
0
45
0
0
70
75
0
75
45
15
85
0
40
20
0
0
0
0
25
20
0


Foxtail, Green
70
80
0
30
—
85
65
98
80
0
80
60
0
50
50
30
60
0
20
5
70
0
0
—
0
5
30



Galium

50
80
10
40
80
70
0
65
40
0
50
60
80
95
75
0
0
0
0
0
90
70
0
0
0
0
35


Goosegrass
100
90
0
100
100
98
95
98
100
95
100
100
95
98
100
100
100
95
95
98
98
98
95
98
40
75
85


Johnsongrass
75
65
0
80
60
80
0
75
45
10
75
45
0
20
5
75
55
0
45
20
—
0
0
0
0
55
0



Kochia

—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
45
70
100
100
0
80
70


Lambsquarters
100
100
98
98
100
100
100
100
100
90
100
100
95
100
98
100
100
98
98
98
100
98
98
98
98
98
98


Morningglory
0
0
0
0
0
0
0
0
—
0
—
100
80
0
20
0
20
0
0
0
0
0
0
0
0
20
15


Nightshade
95
95
40
95
100
98
100
98
100
95
100
100
98
100
98
95
98
98
98
98
98
95
95
95
85
95
95


Nutsedge, Yellow
45
0
0
60
0
45
35
60
10
55
45
20
60
85
70
25
80
45
80
75
65
70
25
15
0
30
65


Oat, Wild
10
0
0
0
0
0
0
0
0
0
0
0
0
0
0
5
0
0
0
0
0
0
0
0
0
0
0


Pigweed
100
100
100
100
100
100
100
98
95
85
100
100
100
100
100
100
98
95
100
98
100
100
98
98
75
98
98


Ragweed
80
75
10
70
45
75
20
90
80
100
80
85
75
95
70
80
75
65
65
75
90
75
20
65
50
0
25


Russian Thistle
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
0
0
—


Ryegrass, Italian
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Soybean
45
0
0
0
0
0
0
0
0
0
0
0
80
0
0
0
70
0
—
—
0
0
80
0
—
—
—


Sunflower
70
0
0
0
5
55
0
70
0
0
65
75
75
75
70
10
55
60
60
55
65
45
10
15
0
0
20


Surinam Grass
60
95
45
60
10
75
5
85
60
5
98
90
—
95
98
25
85
0
95
65
75
0
20
0
85
80
10


Velvetleaf
85
85
0
60
45
85
80
90
65
45
90
95
100
85
85
98
98
98
90
80
90
85
75
90
75
80
85


Wheat
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0













62 g ai/ha
31 g ai/ha



Compounds
Compounds


































68
69
72
73
74
75
77
81
113
119
120
193
217
218
219
220
243
244
245
255
2
3
7
9
10
11





Bermudagrass
98
100
98
98
98
100
100
100
95
100
100
95
100
100
100
98
100
100
100
100
98
10
0
98
45
98


Blackgrass
0
0
0
0
0
0
0
0
0
30
50
0
0
0
35
20
10
35
5
20
0
0
0
0
0
0


Bromegrass, Downy
0
0
0
5
0
0
0
0
10
50
30
5
0
0
0
0
40
0
0
0
0
0
0
0
0
0


Cocklebur
10
0
50
0
45
20
0
10
75
—
35
75
—
0
75
0
75
90
0
—
0
10
0
0
0
35


Corn
0
0
0
0
0
0
0
40
0
40
—
0
0
0
0
0
75
25
5
0
0
0
0
0
0
0


Crabgrass, Large
95
100
100
98
98
100
98
100
98
100
100
100
100
20
98
75
100
100
100
95
15
0
0
0
0
60


Cupgrass, Woolly
20
0
0
20
0
—
0
55
50
75
70
70
5
0
10
0
95
55
70
10
0
0
0
0
0
0


Foxtail, Giant
20
75
5
70
0
25
0
75
40
85
98
65
40
0
0
0
85
80
10
45
15
0
0
0
0
0


Foxtail, Green
5
70
0
30
0
50
0
90
40
100
98
50
0
30
70
90
100
45
0
80
0
0
0
0
0
0



Galium

70
—
85
30
30
85
20
100
70
85
90
100
10
80
85
50
90
65
60
50
—
0
0
0
0
5


Goosegrass
95
100
98
98
98
100
95
98
90
100
100
100
98
60
100
95
100
100
100
98
85
30
10
75
0
70


Johnsongrass
5
45
0
0
0
10
0
80
5
85
70
0
5
0
15
0
95
85
75
60
60
0
0
0
0
0



Kochia

80
20
75
—
—
90
90
55
80
0
20
70
—
—
—
—
20
90
45
—
100
98
15
15
0
15


Lambsquarters
98
100
98
98
98
100
98
98
100
98
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100
100


Morningglory
55
0
55
0
60
60
65
65
—
95
90
90
0
0
0
0
—
90
0
55
0
100
—
0
0
0


Nightshade
98
98
95
95
98
98
98
98
98
98
95
100
100
98
98
90
98
100
100
90
98
50
80
100
100
85


Nutsedge, Yellow
70
0
70
65
55
80
80
75
80
95
90
65
65
75
45
0
80
60
0
25
15
5
0
0
0
0


Oat, Wild
0
0
0
0
0
0
0
0
5
45
10
5
0
0
0
0
85
5
0
0
—
0
0
0
0
0


Pigweed
98
100
98
100
98
100
100
100
98
90
100
100
100
100
100
100
98
100
95
100
100
85
100
50
100
100


Ragweed
75
65
70
60
98
75
75
85
90
80
80
100
60
95
75
60
95
95
85
75
60
65
0
55
98
65


Russian Thistle
—
100
30
—
80
—
—
100
—
100
80
98
—
—
—
—
100
—
—
—
—
—
—
—
—
—


Ryegrass, Italian
0
0
0
0
0
0
0
0
5
100
100
0
0
0
0
0
10
0
0
0
0
0
0
0
0
0


Soybean
—
—
—
—
—
—
—
—
65
55
70
60
0
65
0
0
75
80
10
0
15
0
0
0
10
25


Sunflower
60
0
25
20
55
55
75
75
80
60
—
80
75
80
45
45
85
80
70
60
50
50
0
45
0
75


Surinam Grass
50
100
75
100
80
60
20
100
80
98
100
15
75
65
10
20
98
100
100
85
15
0
0
0
0
0


Velvetleaf
100
70
100
100
100
100
100
100
100
80
100
100
100
85
75
70
100
100
100
95
75
50
40
98
55
100


Wheat
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
40
0
0
0
0
0
0
0
0
0












31 g ai/ha



Compounds




































12
14
24
26
27
29
33
34
36
37
38
39
40
42
44
45
46
47
48
49
50
51
52
53
55
56
58
59





Bermudagrass
100
70
95
5
70
98
98
100
95
10
98
85
98
90
100
98
0
100
100
—
100
95
98
—
95
98
98
10


Blackgrass
0
0
0
0
0
5
0
0
20
0
0
0
0
0
5
0
0
0
0
0
0
0
0
0
0
0
0
0


Bromegrass, Downy
0
0
0
0
0
0
0
—
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Cocklebur
25
0
10
10
0
5
25
0
—
0
0
0
65
0
—
—
0
—
—
0
—
0
0
10
0
0
0
0


Corn
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Crabgrass, Large
0
5
90
0
5
98
85
55
20
0
60
55
70
45
65
45
45
75
75
75
98
75
60
75
10
80
95
55


Cupgrass, Woolly
0
0
5
0
0
5
10
100
0
0
0
0
0
0
0
45
10
0
10
0
0
10
0
0
0
0
10
10


Foxtail, Giant
0
0
30
5
0
10
10
15
10
0
0
0
10
0
20
0
0
45
20
0
45
0
0
5
0
0
10
0


Foxtail, Green
0
0
0
0
0
0
0
50
35
0
20
—
0
65
0
0
0
65
60
0
50
50
0
60
0
0
0
—



Galium

0
0
0
0
0
50
0
10
10
0
0
70
50
0
0
40
0
50
0
0
70
0
0
0
0
0
0
0


Goosegrass
85
70
85
5
80
95
80
95
0
0
95
85
80
50
90
80
85
95
98
20
95
98
98
98
45
90
95
98


Johnsongrass
0
5
20
0
0
0
0
20
0
0
10
0
10
0
10
0
0
65
20
0
0
0
10
10
0
10
10
—



Kochia

15
85
100
80
100
98
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
0


Lambsquarters
100
100
98
98
100
100
98
100
98
95
98
100
100
100
100
100
90
100
100
95
100
95
98
98
95
95
85
98


Morningglory
40
100
100
100
100
100
0
0
0
0
0
0
0
0
0
0
0
0
0
45
0
0
0
0
0
0
0
—


Nightshade
100
85
90
85
80
90
80
55
80
0
90
50
65
100
95
98
95
100
100
98
100
98
90
98
60
85
90
95


Nutsedge, Yellow
25
0
30
10
0
0
0
10
0
0
10
0
10
10
45
0
25
45
20
60
80
55
0
65
0
20
20
55


Oat, Wild
0
0
0
0
0
0
0
10
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Pigweed
100
90
98
98
100
100
100
100
100
100
100
90
98
100
98
85
85
98
100
100
90
100
90
95
45
98
85
90


Ragweed
90
70
85
65
85
80
80
75
35
0
40
0
75
0
20
45
100
45
65
70
75
65
80
65
55
20
20
75


Russian Thistle
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—


Ryegrass, Italian
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0


Soybean
60
25
45
50
70
20
60
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
20
10
—


Sunflower
95
50
85
60
75
75
65
55
0
0
0
0
20
0
10
0
0
65
0
60
55
20
10
15
10
0
0
55


Surinam Grass
35
0
65
0
0
0
0
5
70
0
40
0
40
0
65
45
0
85
80
0
75
95
10
75
0
55
40
5


Velvetleaf
90
70
98
50
55
10
80
75
65
0
55
15
80
75
75
0
0
80
75
95
85
75
80
80
75
85
75
75


Wheat
0
0
0
0
0
0
0
—
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0












31 g ai/ha



Compounds


































61
62
63
64
66
67
68
69
72
73
74
75
77
81
113
119
120
193
217
218
219
220
243
244
245
255





Bermudagrass
20
20
75
50
20
45
95
98
95
50
—
98
55
100
95
100
100
75
98
98
98
80
100
100
98
100


Blackgrass
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
30
5
0
0
0
30
10
0
35
0
0


Bromegrass, Downy
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
10
0
0
0
0
0
0
0
0
0


Cocklebur
0
0
0
0
0
0
0
0
10
0
10
10
0
0
45
0
0
—
—
—
—
0
—
—
0
—


Corn
0
0
0
0
0
0
0
0
0
0
0
0
0
40
0
0
0
0
0
0
0
0
65
5
0
0


Crabgrass, Large
70
0
50
50
70
40
65
98
95
85
98
98
70
100
70
100
98
100
95
0
10
0
100
98
60
80


Cupgrass, Woolly
0
0
0
0
25
0
5
0
0
10
0
5
0
40
5
65
50
10
0
0
0
0
75
45
50
0


Foxtail, Giant
0
0
0
20
15
0
0
5
0
0
0
0
0
60
5
55
75
0
5
0
0
0
55
60
0
15


Foxtail, Green
0
0
0
0
0
0
0
—
0
0
0
5
0
80
10
95
95
5
0
0
20
80
35
0
0
0



Galium

70
0
0
0
0
0
0
—
0
—
20
60
0
85
50
65
80
75
0
60
75
0
85
55
20
0


Goosegrass
80
15
90
30
35
85
80
95
60
85
98
95
55
98
75
100
100
98
95
10
98
65
98
98
95
80


Johnsongrass
0
0
0
0
0
0
0
5
0
0
0
0
0
10
0
50
35
0
0
0
0
0
70
70
65
0



Kochia

0
98
0
0
80
70
80
0
45
0
80
80
85
45
80
0
0
20
—
—
—
—
15
85
0
—


Lambsquarters
90
98
98
95
98
98
98
98
98
95
98
98
98
98
98
95
100
100
95
100
100
100
100
100
100
98


Morningglory
0
0
0
0
0
0
0
0
0
0
10
0
0
—
—
60
0
75
0
0
0
0
—
85
0
40


Nightshade
90
10
80
55
80
70
98
95
95
75
85
95
98
98
98
90
90
100
95
98
90
65
90
98
98
75


Nutsedge, Yellow
25
15
10
0
10
0
0
0
40
20
20
60
75
10
65
75
70
10
60
45
0
0
65
20
0
10


Oat, Wild
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
5
0
0
0
—
30
0
0
0


Pigweed
0
45
95
55
98
98
95
98
98
95
98
98
100
100
98
80
95
98
95
100
100
100
75
100
80
100


Ragweed
50
0
65
0
0
25
10
65
55
45
10
75
50
60
55
80
80
100
60
85
45
15
85
70
75
65


Russian Thistle
—
—
—
—
—
85
—
100
0
0
0
—
—
100
—
100
—
90
—
—
—
—
100
—
—
—


Ryegrass, Italian
—
0
0
0
0
0
0
0
0
0
0
0
0
0
0
100
100
0
0
0
0
0
0
0
0
0


Soybean
—
0
0
—
—
—
—
—
—
—
—
—
—
—
0
10
15
40
0
0
0
—
65
70
0
0


Sunflower
0
0
5
0
0
0
0
0
25
0
0
30
60
60
75
40
45
70
70
75
0
0
80
80
45
45


Surinam Grass
0
5
0
0
35
0
45
80
45
85
0
40
0
98
0
90
100
0
45
10
10
10
80
75
95
65


Velvetleaf
80
75
75
65
80
75
95
70
98
100
98
100
95
100
80
75
80
85
95
80
0
45
100
100
95
80


Wheat
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0















16 g ai/ha





Compounds












2
69







Bermudagrass
25
90



Blackgrass
0
0



Bromegrass, Downy
0
0



Cocklebur
0
0



Corn
0
0



Crabgrass, Large
0
75



Cupgrass, Woolly
0
0



Foxtail, Giant
0
0



Foxtail, Green
0
—



Goosegrass
0
55



Johnsongrass
0
0




Kochia

0
—



Lambsquarters
100
95



Morningglory
0
0



Nightshade
55
80



Nutsedge, Yellow
0
0



Oat, Wild
0
0



Pigweed
98
95



Ragweed
25
40



Russian Thistle
—
100



Ryegrass, Italian
0
—



Soybean
0
—



Sunflower
0
0



Surinam Grass
0
75



Velvetleaf
0
0



Wheat
0
0











Test C


Seeds of plant species selected from bluegrass (annual bluegrass, Poa annua), blackgrass (Alopecurus myosuroides), canarygrass (Phalaris minor), chickweed (common chickweed, Stellaria media), galium (catchweed bedstraw, Galium aparine), bromegrass (downy bromegrass, Bromus tectorum), field poppy (Papaver rhoeas), field violet (Viola arvensis), green foxtail (Setaria viridis), deadnettle (henbit deadnettle, Lamium amplexicaule), Italian ryegrass (Lolium multiflorum), kochia (Kochia scoparia), lambsquarters (Chenopodium album), oilseed rape (Brassica napus), pigweed (Amaranthus retroflexus), Russian thistle (Salsola iberica), spring barley (Hordeum vulgare), spring wheat (Triticum aestivum), buckwheat (wild buckwheat, Polygonum convolvulus), wild mustard (Sinapis arvensis), wild oat (Avena fatua), wild radish (Raphanus raphanistrum), windgrass (Apera spica-venti), winter barley (Hordeum vulgare), and winter wheat (Triticum aestivum) were planted and treated postemergence with test chemicals formulated in a non-phytotoxic solvent mixture which included a surfactant. Plants ranged in height from 2 to 18 cm (1- to 4-leaf stage).


Treated plants and controls were maintained in a controlled growth environment for 14 days after which time all test plants were visually evaluated and compared to controls. 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







Postemergence









125 g ai/ha



Compounds














2
4
8
11
12
33





Barley, Spring
0
15
30
30
0
0


Barley, Winter
30
35
40
60
0
5


Blackgrass
30
40
35
35
40
35


Bluegrass
65
50
75
80
40
40


Bromegrass, Downy
50
40
40
65
20
20


Buckwheat, Wild
70
100
65
80
50
75


Canarygrass
—
90
10
10
—
5


Chickweed
—
100
98
100
—
100


Deadnettle
100
100
100
100
100
100


Field Poppy
—
50
60
70
—
98


Field Violet
50
60
65
35
40
95


Foxtail, Green
95
95
98
95
90
95



Galium

70
90
90
65
80
60



Kochia

98
95
90
98
75
70


Lambsquarters
98
100
100
100
95
100


Mustard, Wild
—
100
98
100
95
100


Oat, Wild
25
50
30
70
15
10


Oilseed Rape
90
100
100
100
95
100


Pigweed
90
100
98
98
75
98


Radish, Wild
95
95
100
95
90
98


Russian Thistle
95
95
95
95
70
90


Ryegrass, Italian
30
15
35
30
0
10


Wheat, Spring
0
20
20
40
0
10


Wheat, Winter
30
20
30
35
10
5


Windgrass
40
95
60
95
50
40












62 g ai/ha



Compounds













2
8
11
12
33





Barley, Spring
0
20
20
0
0


Barley, Winter
10
20
40
0
0


Blackgrass
20
35
35
30
35


Bluegrass
25
50
65
30
15


Bromegrass, Downy
30
35
65
15
15


Buckwheat, Wild
40
65
80
50
75


Canarygrass
—
10
10
—
5


Chickweed
—
95
98
—
98


Deadnettle
100
98
100
100
98


Field Poppy
—
40
40
—
90


Field Violet
40
65
35
40
95


Foxtail, Green
95
95
95
80
95



Galium

50
90
65
60
50



Kochia

75
85
95
35
60


Lambsquarters
80
98
98
80
100


Mustard, Wild
98
98
98
95
98


Oat, Wild
25
30
50
15
5


Oilseed Rape
70
98
98
80
100


Pigweed
75
98
95
75
95


Radish, Wild
95
98
95
90
95


Russian Thistle
70
95
95
60
90


Ryegrass, Italian
15
20
30
0
10


Wheat, Spring
0
5
35
0
10


Wheat, Winter
0
25
30
0
5


Windgrass
25
20
85
—
25












31 g ai/ha



Compounds














2
4
8
11
12
33





Barley, Spring
0
10
10
15
0
0


Barley, Winter
0
5
20
20
0
0


Blackgrass
0
20
30
20
20
5


Bluegrass
25
35
25
35
20
0


Bromegrass, Downy
20
35
25
50
10
10


Buckwheat, Wild
20
95
65
70
15
65


Canarygrass
—
0
5
5
—
0


Chickweed
—
98
95
95
—
90


Deadnettle
95
98
95
98
100
98


Field Poppy
—
30
20
30
—
80


Field Violet
40
40
65
0
35
90


Foxtail, Green
75
70
95
95
60
95



Galium

30
65
75
30
50
40



Kochia

70
90
70
90
10
50


Lambsquarters
75
100
98
98
80
98


Mustard, Wild
98
98
95
98
95
98


Oat, Wild
15
20
20
25
15
0


Oilseed Rape
60
90
90
95
70
98


Pigweed
40
95
95
95
65
95


Radish, Wild
80
80
95
95
80
95


Russian Thistle
60
70
90
80
60
80


Ryegrass, Italian
0
10
0
5
0
0


Wheat, Spring
0
15
5
20
0
10


Wheat, Winter
0
0
10
30
0
0


Windgrass
20
35
10
70
20
20












16 g ai/ha



Compounds













2
8
11
12
33





Barley, Spring
0
0
0
0
0


Barley, Winter
0
0
0
0
0


Blackgrass
0
20
20
0
0


Bluegrass
0
5
—
10
0


Bromegrass, Downy
10
10
30
0
0


Buckwheat, Wild
15
65
65
10
60


Canarygrass
—
0
5
—
0


Chickweed
—
95
95
—
90


Deadnettle
95
85
95
100
95


Field Poppy
—
0
20
—
80


Field Violet
0
10
0
35
65


Foxtail, Green
65
95
95
50
80



Galium

5
50
20
5
35



Kochia

65
65
70
0
35


Lambsquarters
70
98
98
70
98


Mustard, Wild
98
—
98
80
98


Oat, Wild
0
20
25
0
0


Oilseed Rape
60
80
90
50
90


Pigweed
35
95
75
65
75


Radish, Wild
65
85
95
60
90


Russian Thistle
35
90
80
60
80


Ryegrass, Italian
0
0
0
0
0


Wheat, Spring
0
5
5
0
10


Wheat, Winter
0
10
0
0
0


Windgrass
5
0
60
5
0










Preemergence









Compounds










2
12














125 g ai/ha











Barley, Spring
0
0



Barley, Winter
0
0



Blackgrass
0
0



Bluegrass
0
35



Bromegrass, Downy
0
0



Buckwheat, Wild
0
40



Canarygrass
10
20



Chickweed
98
50



Deadnettle
98
100



Field Poppy
100
98



Field Violet
0
0



Foxtail, Green
0
0




Galium

50
35




Kochia

90
25



Lambsquarters
100
100



Mustard, Wild
35
—



Oat, Wild
0
0



Oilseed Rape
65
40



Pigweed
85
65



Radish, Wild
0
0



Ryegrass, Italian
0
0



Wheat, Spring
0
0



Wheat, Winter
0
0



Windgrass
25
40











62 g ai/ha











Barley, Spring
0
0



Barley, Winter
0
0



Blackgrass
0
0



Bluegrass
0
20



Bromegrass, Downy
0
0



Buckwheat, Wild
0
0



Canarygrass
0
—



Chickweed
98
—



Deadnettle
95
90



Field Poppy
95
98



Field Violet
0
0



Foxtail, Green
0
0




Galium

0
35




Kochia

30
5



Lambsquarters
0
70



Mustard, Wild
5
5



Oat, Wild
0
0



Oilseed Rape
35
30



Pigweed
65
50



Radish, Wild
0
0



Russian Thistle
0
0



Ryegrass, Italian
0
0



Wheat, Spring
0
0



Wheat, Winter
0
0



Windgrass
25
40











31 g ai/ha











Barley, Spring
0
0



Barley, Winter
0
0



Blackgrass
0
0



Bluegrass
0
0



Bromegrass, Downy
0
0



Buckwheat, Wild
0
0



Canarygrass
0
—



Chickweed
98
—



Deadnettle
75
50



Field Poppy
75
80



Field Violet
0
0



Foxtail, Green
0
0




Galium

—
0




Kochia

5
5



Lambsquarters
0
20



Mustard, Wild
0
—



Oat, Wild
0
0



Oilseed Rape
20
20



Pigweed
20
0



Radish, Wild
0
0



Russian Thistle
0
0



Ryegrass, Italian
0
0



Wheat, Spring
0
0



Wheat, Winter
0
0



Windgrass
15
20











16 g ai/ha











Barley, Spring
0
0



Barley, Winter
0
0



Blackgrass
0
0



Bluegrass
0
0



Bromegrass, Downy
0
0



Buckwheat, Wild
0
0



Canarygrass
0
—



Chickweed
75
—



Deadnettle
0
35



Field Poppy
—
50



Field Violet
0
0



Foxtail, Green
0
0




Galium

—
0




Kochia

5
5



Lambsquarters
0
0



Mustard, Wild
0
0



Oat, Wild
0
0



Oilseed Rape
0
0



Pigweed
0
0



Radish, Wild
0
0



Russian Thistle
0
0



Ryegrass, Italian
0
0



Wheat, Spring
0
0



Wheat, Winter
0
0



Windgrass
0
20










Test D


Seeds of plant species selected from bermudagrass (Cynodon dactylon), Surinam grass (Brachiaria decumbens), large crabgrass (Digitaria sanguinalis), green foxtail (Setaria viridis), goosegrass (Eleusine indica), j ohnsongrass (Sorghum halepense), kochia (Kochia scoparia), morningglory (pitted morningglory, Ipomoea lacunosa), nutsedge (purple nutsedge, Cyperus rotundus), ragweed (common ragweed, Ambrosia elatior), black mustard (Brassica nigra), guineagrass (Panicum maximum), dallisgrass (Paspalum dilatatum), barnyardgrass (Echinochloa crus-galli), sandbur (southern sandbur, Cenchrus echinatus), sowthistle (common sowthistle, Sonchus oleraceous), prickly sida (Sida spinosa), Italian ryegrass (Lolium multiflorum), purslane (common purslane, Portulaca oleracea), signalgrass (broadleaf signalgrass, Brachiaria platyphylla), groundsel (common groundsel, Senecio vulgaris), chickweed (common chickweed, Stellaria media), dayflower (Virginia (VA) dayflower, Commelina virginica), bluegrass (annual bluegrass, Poa annua), naked crabgrass (Digitaria nuda), itchgrass (Rottboellia cochinchinensis), quackgrass (Elytrigia repens), field bindweed (Convolvulus arvensis), spanishneedles (Bidens bipinnata), mallow (common mallow, Malva sylvestris) and Russian thistle (Salsola kali), 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 from these weed species were treated with postemergence applications of the 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 14 to 21 days, after which time all species were visually evaluated and compared to controls. 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







Postemergence









250 g ai/ha



Compounds















226
235
238
240
243
244
245





Barnyardgrass
95
95
95
95
90
90
90


Bermudagrass
98
95
95
95
95
95
80


Black Mustard
85
98
98
98
98
98
98


Bluegrass
30
50
40
35
35
20
35


Chickweed
85
70
50
70
70
60
50


Crabgrass, Large
85
80
80
70
85
75
75


Crabgrass, Naked
75
—
—
—
—
—
—


Dallisgrass
35
80
75
75
90
80
85


Dayflower, VA
65
75
75
75
75
70
75


Field Bindweed
80
70
50
70
70
70
70


Foxtail, Green
98
98
95
98
98
100 
95


Goosegrass
75
75
75
80
75
70
75


Groundsel
100 
100 
100 
100 
100 
100 
100 


Guineagrass
80
75
75
80
85
75
85


Itchgrass
90
90
80
80
85
75
75


Johnsongrass
90
85
80
95
75
75
75



Kochia

70
85
75
70
75
65
75


Mallow
65
70
60
60
70
70
70


Morningglory
80
95
90
95
85
75
80


Nutsedge, Purple
 5
40
20
20
50
35
20


Prickly Sida
75
75
65
75
80
60
70


Purslane
70
70
60
50
50
50
30


Quackgrass
35
70
40
50
75
65
65


Ragweed
98
80
75
90
75
85
75


Russian Thistle
70
60
50
35
60
65
70


Ryegrass, Italian
15
35
 5
35
65
60
50


Sandbur
75
75
85
90
80
75
75


Signalgrass
65
95
65
85
95
35
75


Sowthistle
98
98
95
98
98
100 
95


Spanishneedles
80
85
75
75
70
75
75


Surinam Grass
90
85
85
95
85
80
75












125 g ai/ha



Compounds






















47
51
52
59
66
85
87
113
128
226
228
233
235
238





Barnyardgrass
70
70
80
75
75
70
70
80
90
95
80
85
95
85


Bermudagrass
90
85
80
80
65
90
85
80
90
95
70
70
95
95


Black Mustard
100 
100 
98
98
98
85
100 
100 
95
80
50
100 
98
98


Bluegrass
 0
 0
35
 5
 0
 5
 0
 0
 0
10
 5
 0
35
20


Chickweed
65
70
100 
—
95
100 
100 
—
70
35
75
60
60
40


Crabgrass, Large
65
35
70
70
35
75
75
70
70
75
75
60
75
75


Crabgrass, Naked
65
65
95
70
70
80
75
75
75
70
—
70
—
—


Dallisgrass
15
70
75
50
60
80
75
70
60
30
 5
35
80
70


Dayflower, VA
30
20
60
—
30
80
70
60
70
—
85
60
75
70


Field Bindweed
65
60
70
60
 0
75
40
—
65
70
70
70
65
—


Foxtail, Green
95
65
95
35
80
65
60
90
70
80
80
35
98
80


Goosegrass
65
65
80
65
75
75
65
65
70
70
70
65
75
75


Groundsel
100 
100 
100 
100 
80
100 
100 
100 
100 
95
100 
100 
100 
100 


Guineagrass
30
50
75
20
30
60
30
70
35
80
15
50
75
65


Itchgrass
10
80
65
75
40
70
30
70
65
70
65
80
80
75


Johnsongrass
65
70
—
60
60
80
60
75
65
80
70
50
85
75



Kochia

30
20
40
50
40
60
60
50
40
70
75
35
70
65


Mallow
65
20
75
40
60
75
70
20
40
50
65
 0
70
50


Morningglory
50
65
70
50
90
90
50
90
70
70
50
70
95
80


Nutsedge, Purple
20
20
40
25
30
65
50
50
50
 0
15
 0
30
20


Prickly Sida
90
75
90
70
98
98
95
70
80
70
65
60
70
50


Purslane
30
35
75
50
75
90
35
75
50
65
35
40
60
60


Quackgrass
 5
 0
20
 0
 5
20
 5
30
 5
20
 5
25
40
30


Ragweed
95
85
95
80
 5
100 
98
80
90
90
75
98
80
75


Russian Thistle
—
—
—
65
—
—
35
20
—
40
65
10
50
50


Ryegrass, Italian
30
 0
35
 5
15
20
 5
50
 5
 0
 5
 5
 5
 5


Sandbur
35
60
80
25
90
95
35
60
35
75
5
75
75
75


Signalgrass
20
50
90
20
30
75
60
75
35
65
20
35
90
60


Sowthistle
100 
100 
100 
100 
90
100 
100 
100 
100 
98
98
100 
98
95


Spanishneedles
70
70
80
70
80
95
70
60
65
75
70
60
80
70


Surinam Grass
70
80
90
60
90
85
40
—
50
90
70
60
75
75












25 g ai/ha



Compounds














240
243
244
245






Barnyardgrass
95
80
85
85



Bermudagrass
95
95
95
80



Black Mustard
98
98
95
98



Bluegrass
35
35
10
35



Chickweed
60
60
40
50



Crabgrass, Large
65
85
75
75



Crabgrass, Naked
—
—
—
—



Dallisgrass
75
90
75
80



Dayflower, VA
70
70
65
65



Field Bindweed
70
70
65
60



Foxtail, Green
98
90
95
95



Goosegrass
80
70
70
70



Groundsel
100 
100 
100 
100 



Guineagrass
80
75
75
75



Itchgrass
80
75
75
75



Johnsongrass
95
70
75
75




Kochia

65
70
50
70



Mallow
60
70
60
50



Morningglory
90
85
75
80



Nutsedge, Purple
 5
25
10
 5



Prickly Sida
75
70
40
50



Purslane
—
50
50
30



Quackgrass
35
70
50
40



Ragweed
80
75
80
75



Russian Thistle
—
30
60
60



Ryegrass, Italian
35
30
35
20



Sandbur
90
75
75
75



Signalgrass
75
75
25
50



Sowthistle
98
95
100 
95



Spanishneedles
75
70
75
70



Surinam Grass
95
75
80
75












62 g ai/ha



Compounds






















47
51
52
59
66
85
87
113
128
226
233
235
238
240





Barnyardgrass
70
70
75
60
70
65
60
80
70
85
85
80
80
95


Bermudagrass
70
80
75
70
65
80
70
80
80
95
70
95
90
95


Black Mustard
100 
—
98
65
50
75
100 
100 
95
80
50
80
95
80


Bluegrass
 0
 0
35
 0
 0
 5
 0
 0
 0
10
 0
20
 5
35


Chickweed
—
—
98
70
35
100 
75
—
65
35
—
30
35
50


Crabgrass, Large
60
35
70
50
25
75
70
70
60
75
50
75
70
65


Crabgrass, Naked
35
—
95
50
65
75
70
70
70
65
60
—
—
—


Dallisgrass
15
30
70
20
35
65
50
60
30
20
10
75
65
70


Dayflower, VA
20
10
30
60
 0
60
60
60
60
50
35
70
65
60


Field Bindweed
50
20
70
30
 0
75
25
65
65
70
50
65
50
70


Foxtail, Green
50
40
85
20
65
35
35
70
65
70
30
95
80
98


Goosegrass
65
65
75
50
65
75
65
65
65
70
60
75
70
70


Groundsel
100 
100 
100 
100 
80
100 
100 
100 
100 
90
90
100 
100 
100 


Guineagrass
20
30
75
20
10
35
20
50
30
80
40
75
50
65


Itchgrass
 5
40
65
15
35
65
30
65
40
70
70
75
70
75


Johnsongrass
35
60
85
40
50
80
40
65
50
80
50
70
70
90



Kochia

20
 5
 0
20
25
20
35
50
30
60
30
60
50
65


Mallow
65
 0
65
 5
60
70
70
 0
40
50
 0
50
35
40


Morningglory
—
20
70
50
90
75
40
90
70
70
70
75
80
80


Nutsedge, Purple
10
15
35
20
20
50
20
35
35
 0
 0
 5
10
 5


Prickly Sida
80
65
80
70
98
95
80
70
65
65
50
65
30
65


Purslane
30
35
65
35
75
90
35
50
30
50
30
60
60
35


Quackgrass
 0
 0
15
 0
 5
15
 0
20
 0
 0
10
30
 5
30


Ragweed
80
80
95
—
 0
80
95
75
90
90
75
70
75
75


Russian Thistle
20
—
—
—
—
—
—
20
20
—
—
30
40
35


Ryegrass, Italian
20
 0
15
 5
 0
15
 0
35
 0
 0
 5
 5
 5
35


Sandbur
20
25
75
 5
35
65
20
60
 5
75
70
75
75
70


Signalgrass
15
50
80
10
30
60
60
60
35
40
25
90
35
75


Sowthistle
100 
100 
98
100 
70
100 
98
100 
100 
98
—
98
95
98


Spanishneedles
65
60
80
70
80
90
60
50
50
75
50
70
70
65


Surinam Grass
60
70
80
50
90
75
40
80
30
70
50
75
75
70












62 g ai/ha



Compounds













243
244
245






Barnyardgrass
80
80
85



Bermudagrass
85
80
80



Black Mustard
75
75
95



Bluegrass
 5
10
20



Chickweed
50
20
25



Crabgrass, Large
80
75
70



Crabgrass, Naked
—
—
—



Dallisgrass
80
75
75



Dayflower, VA
65
50
35



Field Bindweed
70
35
50



Foxtail, Green
85
90
90



Goosegrass
70
60
70



Groundsel
100 
100 
100 



Guineagrass
75
75
75



Itchgrass
75
70
70



Johnsongrass
70
70
75




Kochia

60
50
65



Mallow
60
50
50



Morningglory
85
70
75



Nutsedge, Purple
25
 0
 5



Prickly Sida
65
35
50



Purslane
50
50
 5



Quackgrass
40
40
35



Ragweed
70
70
75



Russian Thistle
30
40
60



Ryegrass, Italian
20
15
 5



Sandbur
75
70
70



Signalgrass
75
20
40



Sowthistle
90
95
95



Spanishneedles
65
65
70



Surinam Grass
75
75
75












31 g ai/ha



Compounds






















47
51
52
59
66
85
87
113
128
226
228
233
235
238





Barnyardgrass
70
70
75
60
65
50
50
75
70
85
20
75
80
75


Bermudagrass
50
75
75
40
50
75
65
70
70
90
70
70
80
80


Black Mustard
100 
95
90
40
20
60
65
—
95
65
20
50
80
80


Bluegrass
 0
 0
25
 0
 0
 0
 0
 0
 0
 0
 0
 0
 5
 0


Chickweed
65
—
90
70
—
80
75
70
—
20
35
50
 5
30


Crabgrass, Large
50
35
70
35
25
60
65
60
50
65
65
40
70
50


Crabgrass, Naked
35
50
75
30
50
50
60
65
65
60
—
50
—
—


Dallisgrass
10
20
65
10
35
25
25
10
20
15
 0
10
70
10


Dayflower, VA
15
10
 5
—
 0
30
35
40
50
50
35
35
60
35


Field Bindweed
40
 5
70
 5
 0
75
15
65
50
70
65
50
60
35


Foxtail, Green
35
20
70
 5
35
25
30
60
40
65
70
10
70
75


Goosegrass
65
65
75
20
50
65
35
50
40
70
50
50
75
50


Groundsel
100 
98
100 
90
60
100 
98
90
100 
80
100 
50
100 
100 


Guineagrass
20
30
70
10
 5
20
20
25
30
80
 0
30
75
25


Itchgrass
 5
20
50
15
15
35
 0
10
40
50
40
65
70
70


Johnsongrass
15
35
75
35
20
50
30
40
40
50
65
35
70
60



Kochia

10
 5
 0
 5
25
10
35
40
30
60
65
20
20
20


Mallow
50
 0
65
 5
30
65
60
 0
 5
35
40
 0
10
25


Morningglory
 5
20
65
40
70
70
40
60
65
50
50
60
75
70


Nutsedge, Purple
 0
 0
20
 0
 5
30
10
10
10
 0
 5
 0
 5
 5


Prickly Sida
70
50
65
40
98
95
80
60
60
40
40
50
65
30


Purslane
20
20
65
35
50
80
25
30
30
50
—
30
60
60


Quackgrass
 0
 0
10
 0
 5
 0
 0
 0
 0
 0
 0
 0
 5
 5


Ragweed
75
75
95
70
 0
80
80
70
75
80
75
75
70
70


Russian Thistle
—
—
—
—
—
—
—
 0
 0
—
20
—
30
30


Ryegrass, Italian
10
 0
 0
 0
 0
 0
 0
20
 0
 0
 0
 0
 5
 5


Sandbur
 5
25
65
 5
35
50
 5
10
 5
60
 5
65
75
50


Signalgrass
 5
35
60
 5
10
35
30
40
30
35
15
 5
65
20


Sowthistle
100 
98
95
100 
65
100 
98
95
100 
90
95
100 
98
95


Spanishneedles
40
50
75
50
70
75
60
35
50
70
65
35
65
65


Surinam Grass
50
60
65
35
60
75
40
75
25
65
 5
—
75
75












31 g ai/ha



Compounds














240
243
244
245






Barnyardgrass
80
75
80
80



Bermudagrass
85
75
80
80



Black Mustard
70
50
50
75



Bluegrass
 5
 5
 0
 5



Chickweed
25
35
15
 5



Crabgrass, Large
40
75
70
70



Crabgrass, Naked
—
—
—
—



Dallisgrass
 5
75
40
65



Dayflower, VA
35
35
30
20



Field Bindweed
60
65
20
50



Foxtail, Green
95
80
75
85



Goosegrass
70
65
50
70



Groundsel
100 
98
100 
95



Guineagrass
40
70
70
75



Itchgrass
75
75
60
70



Johnsongrass
70
70
70
70




Kochia

20
50
25
50



Mallow
10
50
50
35



Morningglory
65
75
65
70



Nutsedge, Purple
 0
20
 0
 5



Prickly Sida
35
60
25
30



Purslane
 0
35
25
 0



Quackgrass
25
35
20
20



Ragweed
70
65
65
70



Russian Thistle
35
20
20
25



Ryegrass, Italian
 0
 0
 5
 5



Sandbur
70
75
70
65



Signalgrass
20
50
20
10



Sowthistle
98
90
75
95



Spanishneedles
65
60
65
65



Surinam Grass
70
75
75
75












16 g ai/ha



Compounds




















47
51
52
59
66
85
87
113
128
233






Barnyardgrass
70
65
75
40
35
30
35
65
35
65



Bermudagrass
50
65
75
35
5
65
65
65
70
70



Black Mustard
95
70
65
10
 0
35
40
100 
95
20



Bluegrass
 0
 0
15
 0
 0
 0
 0
 0
 0
 0



Chickweed
50
—
75
—
—
—
75
—
60
—



Crabgrass, Large
20
25
65
35
20
60
40
60
40
20



Crabgrass, Naked
20
35
70
20
—
—
50
50
35
30



Dallisgrass
 5
20
60
10
35
15
25
10
10
 0



Dayflower, VA
10
10
 5
25
 0
20
10
20
50
15



Field Bindweed
35
 5
50
 5
 0
65
 0
50
50
10



Foxtail, Green
 5
10
70
 0
20
20
 5
25
25
 5



Goosegrass
40
35
65
20
50
40
30
40
35
40



Groundsel
100 
85
100 
70
—
100 
98
90
100 
30



Guineagrass
10
20
50
10
 5
10
10
25
20
20



Itchgrass
 0
 0
25
 0
10
30
 0
 0
 0
50



Johnsongrass
 5
20
65
30
 0
35
20
40
35
20




Kochia

 0
 5
 0
 5
—
 0
25
25
20
10



Mallow
35
 0
50
 0
25
60
40
 0
 5
 0



Morningglory
 5
 0
50
 0
65
70
40
50
65
50



Nutsedge, Purple
 0
 0
 0
 0
 0
 5
 0
 0
 0
 0



Prickly Sida
60
50
65
40
—
—
70
50
50
30



Purslane
20
10
65
35
—
75
10
30
30
30



Quackgrass
 0
 0
 5
 0
 0
 0
 0
 0
 0
 0



Ragweed
75
60
90
70
 0
80
70
70
—
65



Russian Thistle
20
 0
—
—
—
—
—
 0
 0
 0



Ryegrass, Italian
 0
 0
 0
 0
 0
 0
 0
 0
 0
 0



Sandbur
 5
 5
65
 5
—
10
 5
 5
 5
30



Signalgrass
 0
 5
50
 5
 0
20
20
 5
 0
 0



Sowthistle
90
95
80
70
35
100 
90
90
100 
90



Spanishneedles
35
35
75
30
65
75
60
35
35
35



Surinam Grass
35
50
—
30
—
—
30
60
—
30










Preemergence











250 g ai/ha




Compound




243






Barnyardgrass
100



Bermudagrass
100



Black Mustard
100



Bluegrass
100



Crabgrass, Large
100



Crabgrass, Naked
100



Dallisgrass
100



Dayflower, VA
100



Field Bindweed
100



Foxtail, Green
100



Goosegrass
100



Guineagrass
100



Itchgrass
100



Johnsongrass
100




Kochia

100



Mallow
98



Morningglory
100



Nutsedge, Purple
100



Prickly Sida
100



Purslane
100



Quackgrass
98



Ragweed
100



Russian Thistle
100



Ryegrass, Italian
100



Sandbur
100



Signalgrass
100



Spanishneedles
100



Surinam Grass
100












Compounds



















47
51
52
59
66
85
87
113
128
233
243












125 g ai/ha


















Barnyardgrass
 5
10
10
10
75
98
95
35
15
40
100 


Bermudagrass
100 
30
100 
90
 5
100 
98
85
75
85
100 


Black Mustard
100 
100 
100 
100 
80
100 
100 
100 
95
65
100 


Bluegrass
35
 0
20
30
 0
15
35
 0
25
40
95


Chickweed
—
—
95
—
98
100 
—
—
—
—
—


Crabgrass, Large
95
 5
98
65
98
100 
100 
95
—
90
100 


Crabgrass, Naked
98
 0
80
95
25
98
100 
100 
75
65
100 


Dallisgrass
75
90
95
75
95
98
98
100 
98
35
100 


Dayflower, VA
50
 0
40
35
 5
95
65
65
25
100 
100 


Field Bindweed
35
 0
50
60
20
98
70
90
98
85
100 


Foxtail, Green
 0
 0
15
 0
 5
70
10
20
 0
 0
100 


Goosegrass
75
40
98
80
50
98
100 
95
90
100 
100 


Guineagrass
 0
75
—
 0
65
75
75
100 
 0
 0
100 


Itchgrass
 0
 0
 5
20
 0
50
20
 0
20
20
50


Johnsongrass
75
70
95
35
30
95
70
10
65
65
100 



Kochia

100 
50
35
 0
90
95
100 
100 
50
80
100 


Mallow
98
65
—
65
75
98
100 
90
100 
60
80


Morningglory
65
100 
100 
80
95
100 
95
90
90
95
98


Nutsedge, Purple
35
 5
40
80
70
95
75
80
70
 5
100 


Prickly Sida
100 
35
100 
65
90
100 
100 
90
30
70
100 


Purslane
100 
100 
100 
100 
100 
100 
100 
100 
100 
100 
100 


Quackgrass
 0
 0
20
 0
 0
20
 0
 0
 0
 0
85


Ragweed
100 
95
98
100 
 0
100 
98
98
100 
98
100 


Russian Thistle
100 
75
—
100 
—
—
100 
100 
100 
100 
100 


Ryegrass, Italian
 0
 0
15
20
 0
20
30
20
 0
20
98


Sandbur
90
75
98
 0
80
98
95
90
20
85
100 


Signalgrass
90
10
90
 5
 5
95
75
90
 5
35
95


Sowthistle
100 
100 
100 
100 
 0
100 
100 
100 
100 
100 
—


Spanishneedles
95
98
98
90
95
100 
98
95
100 
95
100 


Surinam Grass
—
—
98
100 
98
100 
100 
95
90
100 
100 









62 g ai/ha


















Barnyardgrass
 5
 0
 0
 0
 5
95
50
 0
 5
 5
100 


Bermudagrass
50
 0
90
40
 5
100 
98
70
65
85
100 


Black Mustard
80
75
80
60
35
98
100 
80
85
20
100 


Bluegrass
 0
 0
 0
15
 0
 0
25
 0
25
25
40


Chickweed
—
—
—
—
90
100 
—
—
—
—
—


Crabgrass, Large
 5
 5
75
35
50
100 
95
95
60
25
100 


Crabgrass, Naked
60
 0
20
65
10
95
100 
90
 0
65
100 


Dallisgrass
65
10
50
65
 5
95
80
50
65
 0
100 


Dayflower, VA
50
—
 0
35
 0
90
65
50
10
100 
100 


Field Bindweed
 0
 0
20
20
 0
70
40
65
35
85
100 


Foxtail, Green
 0
 0
 0
 0
 0
40
 0
 0
 0
 0
35


Goosegrass
 5
40
80
20
30
75
95
75
65
98
100 


Guineagrass
 0
 0
50
 0
 0
70
50
100 
 0
 0
100 


Itchgrass
 0
 0
 0
 0
 0
35
20
 0
 0
 0
25


Johnsongrass
 0
20
75
10
 0
80
20
10
15
20
100 



Kochia

100 
 0
25
 0
65
75
100 
100 
50
20
80


Mallow
65
 0
—
65
 5
95
80
 5
70
 0
50


Morningglory
20
30
 0
 0
90
90
80
60
0
95
—


Nutsedge, Purple
10
 5
30
20
35
95
50
20
 0
 0
20


Prickly Sida
65
20
50
 5
 5
100 
100 
70
25
 0
100 


Purslane
95
65
90
100 
60
100 
100 
100 
100 
100 
95


Quackgrass
 0
 0
 0
 0
 0
15
 0
 0
 0
 0
35


Ragweed
100 
65
70
90
 0
100 
98
80
90
95
100 


Russian Thistle
50
75
—
90
—
—
90
100 
95
75
100 


Ryegrass, Italian
 0
 0
 0
 0
 0
10
 0
 0
 0
 0
60


Sandbur
 5
 5
 5
 0
10
60
50
65
20
50
100 


Signalgrass
10
 0
50
 0
 5
75
75
 0
 0
10
75


Sowthistle
100 
98
80
100 
 0
100 
100 
100 
100 
100 
—


Spanishneedles
95
90
95
 0
85
98
85
—
90
85
100 


Surinam Grass
 0
100 
98
100 
95
100 
95
—
80
65
100 









31 g ai/ha


















Barnyardgrass
 0
 0
 0
 0
 0
75
 5
 0
 0
 0
60


Bermudagrass
25
 0
70
 0
 0
100 
65
50
 0
 5
75


Black Mustard
65
50
20
40
 5
60
75
 0
60
 0
80


Bluegrass
 0
 0
 0
 0
 0
 0
20
 0
 0
 0
10


Chickweed
—
—
—
—
20
100 
—
—
—
—
—


Crabgrass, Large
 0
 5
20
35
30
98
75
30
25
 5
100 


Crabgrass, Naked
 0
 0
 0
 0
 0
95
80
 0
 0
 0
100 


Dallisgrass
25
10
10
 0
 5
80
50
50
20
 0
75


Dayflower, VA
35
 0
 0
 0
 0
10
 0
50
 0
80
90


Field Bindweed
 0
 0
—
 0
 0
70
 0
20
 0
 0
100 


Foxtail, Green
 0
 0
 0
 0
 0
 5
 0
 0
 0
 0
20


Goosegrass
 0
20
60
 5
 0
75
35
25
 5
95
100 


Guineagrass
 0
 0
—
 0
 0
10
 0
65
 0
 0
100 


Itchgrass
 0
 0
 0
 0
 0
15
20
 0
 0
 0
10


Johnsongrass
 0
 0
 0
 0
 0
65
 5
 0
 0
 0
95


Kochia
50
—
25
 0
65
20
98
70
 0
 0
—


Mallow
 0
 0
—
65
 0
—
—
 5
70
 0
 0


Morningglory
 0
 0
 0
 0
 0
70
—
60
 0
80
90


Nutsedge, Purple
 0
 0
 5
20
 0
75
 5
10
 0
 0
 5


Prickly Sida
50
20
 0
 0
 0
100 
60
35
 0
 0
85


Purslane
 0
50
60
100 
 0
100 
100 
100 
 0
 0
75


Quackgrass
 0
 0
 0
 0
 0
 0
 0
 0
 0
 0
 0


Ragweed
50
50
50
50
 0
95
98
50
75
70
100 


Russian Thistle
—
—
—
90
—
—
75
65
 0
65
100 


Ryegrass, Italian
 0
 0
 0
 0
 0
 0
 0
 0
 0
 0
50


Sandbur
 0
 0
 0
 0
 5
 5
25
 0
 0
 0
75


Signalgrass
 0
 0
 0
 0
 5
60
 0
 0
 0
 0
—


Sowthistle
65
75
80
95
 0
100 
100 
75
80
50
—


Spanishneedles
95
 0
70
 0
60
98
65
 0
 0
50
100 


Surinam Grass
—
98
98
90
80
100 
50
40
35
 5
100 












16 g ai/ha



Compounds


















47
51
52
59
66
85
87
113
128
233





Barnyardgrass
0
0
0
0
0
60 
0
0
0
0


Bermudagrass
10 
0
30 
0
0
80 
65 
50 
0
5


Black Mustard
0
0
0
20 
0
50 
75 
0
60 
0


Bluegrass
0
0
0
0
0
0
20 
0
0
0


Chickweed
—
—
—
—
0
90 
—
—
—
—


Crabgrass, Large
0
0
0
0
15 
95 
50 
20 
0
0


Crabgrass, Naked
0
0
0
0
0
0
—
0
0
0


Dallisgrass
0
0
5
0
0
50 
50 
5
0
0


Dayflower, VA
35 
0
0
—
0
5
0
50 
—
0


Field Bindweed
0
0
20 
0
0
50 
0
0
0
0


Foxtail, Green
0
0
0
0
0
0
0
0
0
0


Goosegrass
0
20 
5
0
0
65 
35 
25 
0
70 


Guineagrass
0
0
0
0
0
0
0
0
0
0


Itchgrass
0
0
0
0
0
10 
0
0
0
0


Johnsongrass
0
0
0
0
0
50 
0
0
0
0



Kochia

0
0
—
0
0
5
65 
—
0
0


Mallow
0
0
—
0
0
80 
—
0
—
0


Morningglory
0
0
0
0
0
—
10 
60 
—
0


Nutsedge, Purple
0
0
0
0
0
70 
0
0
0
0


Prickly Sida
0
0
0
0
0
90 
50 
0
0
0


Purslane
0
0
0
65 
0
80 
70 
90 
0
0


Quackgrass
0
0
0
0
0
0
0
0
0
0


Ragweed
0
35 
30 
0
0
90 
30 
0
0
50 


Russian Thistle
0
—
0
—
—
—
50 
0
—
50 


Ryegrass, Italian
0
0
0
0
0
0
0
0
0
0


Sandbur
0
0
0
0
0
5
0
0
0
0


Signalgrass
0
0
0
0
0
5
0
0
0
0


Sowthistle
65 
40 
0
0
0
100 
98 
50 
80 
0


Spanishneedles
0
0
35 
0
0
90 
0
0
0
0


Surinam Grass
0
90 
0
5
0
98 
0
—
0
0










Test E


Three plastic pots (ca. 16-cm diameter) for each application were partially filled with sterilized Tama silt loam soil comprising a 35:50:15 ratio of sand, silt and clay and 2.6% organic matter. Separate plantings for each of the three pots were as follows. Seeds from the U.S. of ducksalad (Heteranthera limosa), sedge (smallflower umbrella sedge, Cyperus difformis), ricefield bulrush (Scirpus mucronatus) and redstem (purple redstem, Ammannia coccinea), were planted into one 16-cm pot for each rate. Seeds from the U.S. of flatsedge (rice flatsedge, Cyperus iria), sprangletop (bearded (i.e. Brdd.) sprangletop, Leptochloa fascicularis), one stand of 9 or 10 water seeded rice seedlings (Oryza sativa cv. ‘Japonica-M202’), and two stands of 3 or 4 transplanted rice seedlings (Oryza sativa cv. ‘Japonica-M202’) were planted into one 16-cm pot for each rate. Seeds from the U.S. of barnyardgrass (Echinochloa crus-galli), late watergrass (Echinochloa oryzicola), early watergrass (Echinochloa oryzoides) and junglerice (Echinochloa colona) were planted into one 16-cm pot for each rate. Plantings were sequential so that crop and weed species were at the 2.0 to 2.5-leaf stage at time of treatment.


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. Test pots were maintained in the greenhouse until test completion.


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 days. 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







Flood









500 g ai/ha



Compounds












4
19






Barnyardgrass
60
85



Bulrush, Ricefield
80
75



Ducksalad
100
100



Flatsedge, Rice
90
100



Junglerice
50
80



Redstem
85
85



Rice, Transplanted
15
65



Rice, Water Seeded
50
95



Sedge, Umbrella
100
100



Sprangletop, Brdd.
—
100



Watergrass, Early
65
85



Watergrass, Late
60
55












Compounds














4
19
28
218














250 g ai/ha













Barnyardgrass
60
70
0
95



Bulrush, Ricefield
80
70
65
100



Ducksalad
100
100
100
100



Flatsedge, Rice
40
95
45
75



Junglerice
25
65
0
100



Redstem
80
90
90
80



Rice, Transplanted
0
40
15
10



Rice, Water Seeded
20
70
85
35



Sedge, Umbrella
95
100
100
100



Sprangletop, Brdd.
—
100
—
95



Watergrass, Early
60
65
20
60



Watergrass, Late
15
60
0
70











125 g ai/ha













Barnyardgrass
0
60
0
30



Bulrush, Ricefield
40
70
35
90



Ducksalad
90
95
80
95



Flatsedge, Rice
0
40
0
70



Junglerice
0
50
0
65



Redstem
80
90
50
75



Rice, Transplanted
0
35
15
0



Rice, Water Seeded
10
40
65
20



Sedge, Umbrella
90
100
90
100



Sprangletop, Brdd.
—
95
—
70



Watergrass, Early
0
45
0
20



Watergrass, Late
0
45
0
40












64 g ai/ha



Compounds













19
28
218






Barnyardgrass
60
0
0



Bulrush, Ricefield
50
30
80



Ducksalad
85
0
85



Flatsedge, Rice
40
0
70



Junglerice
0
0
0



Redstem
0
40
65



Rice, Transplanted
0
15
0



Rice, Water Seeded
0
60
0



Sedge, Umbrella
90
85
95



Sprangletop, Brdd.
75
—
70



Watergrass, Early
20
0
20



Watergrass, Late
0
0
40












32 g ai/ha



Compounds










28
218














Barnyardgrass
0
0



Bulrush, Ricefield
20
80



Ducksalad
0
80



Flatsedge, Rice
0
75



Junglerice
0
0



Redstem
0
65



Rice, Transplanted
0
0



Rice, Water Seeded
45
15



Sedge, Umbrella
0
85



Sprangletop, Brdd.
—
65



Watergrass, Early
0
0



Watergrass, Late
0
20










Test F


Test F evaluated the effect of combining compound 2 with bromoxynil. The test species for this experiment was Russian thistle (Salsola iberica), which was prepared by sowing seeds into a blend of loam soil and sand. Test chemicals were formulated in a non-phytotoxic solvent mixture that included a surfactant and applied postemergence to plants ranging in height from 12 to 20 cm.


Plants were grown in a greenhouse using supplemental lighting to maintain a photoperiod of 16 hours; day and night temperatures ranged between 24-30° C. and 19-21° C., respectively. Treatments consisted of Compound 2, bromoxynil, or their combination, using a spray volume of 457 L/ha. Each treatment was replicated three times. Treated plants and untreated controls were maintained in a greenhouse for 15 days, after which time all plants were visually evaluated and compared to the untreated controls. Plant responses were calculated as the mean of the three replicates and summarized in Table F. Visual evaluations were based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. Colby's Equation was used to determine the herbicidal effects expected from the mixtures. Colby's Equation (Colby, S. R. “Calculating Synergistic and Antagonistic Responses of Herbicide Combinations,” Weeds, 15(1), pp 20-22 (1967)) calculates the expected additive effect of herbicidal mixtures, and for two active ingredients is of the form:

Pa+b=Pa+Pb−(PaPb/100)

wherein Pa+b is the percentage effect of the mixture expected from additive contribution of the individual components:

    • Pa is the observed percentage effect of the first active ingredient at the same use rate as in the mixture, and
    • Pb is the observed percentage effect of the second active ingredient at the same use rate as in the mixture.


      The results and additive effects expected from Colby's Equation are listed in Table F1.









TABLE F1







Observed and Expected Results from Compound 2, Bromoxynil, or their


combination.









Postemergence Application Rate










(g a.i./ha)*
Russian Thistle










Cmpd 2
Bromoxynil
Obsd.
Exp.













62
—
42
—


125
—
52
—


—
70
8
—


—
140
13
—


62
70
93
47


125
140
95
58





*Application rates are grams of active ingredient per hectare (g a.i./ha).


“Obsd.” is observed effect.


“Exp.” is expected effect calculated from Colby's Equation.






The results in Table D1 suggest the combination of Compound 2 and bromoxynil have a synergistic action based on the observed injury being greater than the expected values as calculated by the Colby Equation for an additive effect.

Claims
  • 1. A compound of Formula 1R including all stereoisomers, N-oxides, and salts thereof:
  • 2. A compound of claim 1 wherein R2 is 3-thienyl or 2-thienyl.
  • 3. A compound of claim 1 wherein R2 is n-propyl, n-butyl, or cyclopropyl.
  • 4. A compound of the formula
  • 5. A compound of the formula
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Related Publications (1)
Number Date Country
20160024020 A1 Jan 2016 US
Provisional Applications (1)
Number Date Country
61240792 Sep 2009 US
Divisions (2)
Number Date Country
Parent 14573370 Dec 2014 US
Child 14870113 US
Parent 13391647 US
Child 14573370 US