Herbicidal pyrrolesulfonylureas

BACKGROUND OF THE INVENTION
The present invention relates to herbicidal pyrrolesulfonylureas, compositions thereof and a method for their use as preemergence and/or postemergence herbicides or plant growth regulants.
New compounds effective for controlling the growth of undesired vegetation are in constant demand. In the most common situation, such compounds are sought to selectively control the growth of weeds in useful crops such as cotton, rice, corn, wheat and soybeans, to name a few. Unchecked weed growth in such crops can cause significant losses, reducing profit to the farmer and increasing costs to the consumer. In other situations, herbicides are desired which will control all plant growth. Examples of areas in which complete control of all vegetation is desired are areas around railroad tracks, storage tanks and industrial storage areas. There are many products commercially available for these purposes, but the search continues for products which are more effective, less costly and environmentally safe.
The "sulfonylurea" herbicides are an extremely potent class of herbicides discovered within the last few years which generally consist of a sulfonylurea bridge, --SO.sub.2 NHCONH--, linking two aromatic or heteroaromatic rings.
U.S. Pat. No. 4,368,067 discloses herbicidal sulfonylureas of the formula ##STR1## wherein: R.sub.1 is H, C.sub.1 -C.sub.4 alkyl, NO.sub.2, CH, C(O)CCl.sub.3, SO.sub.2 R.sub.11, C(O)R.sub.5 or CO.sub.2 H;
R.sub.2 is H or C.sub.1 -C.sub.4 alkyl;
R.sub.3 is H, C.sub.1 -C.sub.4 alkyl, Cl or Br;
R.sub.4 is H, C.sub.1 -C.sub.4 alkyl, cyanoethyl, C.sub.5 -C.sub.6 cycloalkyl, benzyl, phenyl substituted with Cl or NO.sub.2, or C(O)R.sub.6 ;
R.sub.5 is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy;
R.sub.6 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or NR.sub.7 R.sub.8 ; and
R.sub.7 and R.sub.8 are independently C.sub.1 -C.sub.2 alkyl.
U.S. Pat. No. 4,549,898 discloses herbicidal sulfonamides of the formula ##STR2## wherein: X is O, S, NR.sub.4 or --C(R.sub.5).dbd.N--;
R.sub.2 is H, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, halogen, NO.sub.2, C.sub.1 -C.sub.3 alkoxy, C(W)R.sub.8, SO.sub.2 NR.sub.6 R.sub.7, S(O).sub.n --C.sub.1 -C.sub.3 alkyl or C(O)R.sub.9 ;
R.sub.4 is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 cyanoalkyl, C.sub.3 -C.sub.6 cycloalkyl, benzyl, C(O)C.sub.1 -C.sub.4 alkoxy, C(O)NR.sub.6 R.sub.7 or C(O)C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted by 1 to 3 halogen atoms;
R.sub.6 is H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.4 cyanoalkyl, OCH.sub.3 or OCH.sub.2 CH.sub.3 ;
R.sub.7 is H, C.sub.1 -C.sub.6 alkyl or C.sub.3 -C.sub.6 alkenyl; or
R.sub.6 and R.sub.7, together with the nitrogen atom to which they are attached, form a 5- or 6-membered saturated heterocyclic ring which may contain an oxygen; and
Y is O or S.
EP-A-126,711 discloses herbicidal sulfonamides of the formula ##STR3## wherein: Q is halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, NO.sub.2, NH.sub.2, C.sub.1 -C.sub.4 alkylamino, C.sub.1 -C.sub.4 dialkylamino, CN, C.sub.1 -C.sub.4 alkoxycarbonyl, CHO, C.sub.2 -C.sub.4 alkoxyalkyl, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.1 -C.sub.4 alkenyl or C.sub.1 -C.sub.4 alkynyl;
R.sub.1 is H, halogen, NO.sub.2, CR.sub.6 (OC.sub.1 -C.sub.4 alkyl).sub.2, ##STR4## SO.sub.2 NR.sub.7 R.sub.8, C(O)R.sub.9 or (Y)mR.sub.10 ; X is O, S, NR.sub.5, C(R.sub.5).dbd.N, CH.dbd.CH or ##STR5## R.sub.5 is H, C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.4 alkenyl.
EP-A-161,211 discloses herbicidal sulfonamides of the formula ##STR6## wherein: G is ##STR7## R.sup.2 is ##STR8## Q is O, S or NR.sup.7 ; A is O, S, SO, SO.sub.2 or --(CR.sub.10 R.sub.11).sub.m --;
m is 0, 1 or 2;
R.sup.7 is H, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.6 cycloalkyl, benzyl or phenyl; and
R.sup.10 and R.sup.11 are independently H or C.sub.1 -C.sub.4 alkyl.
SUMMARY OF THE INVENTION
The invention comprises compounds of Formula I, agriculturally suitable compositions thereof and a method of use as preemergence and/or postemergence herbicides or plant growth regulants. ##STR9## W is O or S; R is H or CH.sub.3 ;
R.sup.1 is H; CH.sub.3 ; CH.sub.2 OCH.sub.3 ; CH.sub.2 OC.sub.2 H.sub.5 ; CH.sub.2 CN; CH.sub.2 SCH.sub.3, CH.sub.2 SC.sub.2 H.sub.5 ; C.sub.2 -C.sub.6 alkyl optionally substituted with one C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkylthio, CN or one or more halogens; C.sub.3 -C.sub.4 alkenyl; C.sub.3 -C.sub.4 haloalkenyl; C.sub.3 -C.sub.6 cycloalkyl; C(O)R.sup.5 ; N(CH.sub.3).sub.2 ; or Q.sup.1 ;
R.sup.2 is C.sub.1 -C.sub.4 alkyl optionally substituted with one CN, C.sub.2 -C.sub.3 alkylcarbonyl, methoxycarbonyl, C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkylthio, C.sub.1 -C.sub.2 alkylsulfonyl, S(O).sub.2 NR.sup.6 R.sup.7, OH or one or more halogens; C.sub.2 -C.sub.4 alkenyl optionally substituted with one C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkylthio, CN or one or more halogens; (CH.sub.2).sub.m Q.sup.2 ; CN; C(O)R.sup.8 ; C(O)OR.sup.9 ; C(O)NR.sup.10 R.sup.11 ; C(R.sup.12).dbd.NOR.sup.13 ; C(R.sup.14)(OR.sup.15)(OR.sup.16); S(O).sub.n R.sup.17 ; S(O).sub.2 NR.sup.18 R.sup.19 ; NO.sub.2 ; halogen or OR.sup.73 ;
R.sup.3 is H, halogen or C.sub.1 -C.sub.4 alkyl;
R.sup.4 is H, C.sub.1 -C.sub.4 alkyl optionally substituted with one CN, C.sub.2 -C.sub.3 alkylcarbonyl, methoxycarbonyl, C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkylthio, C.sub.1 -C.sub.2 alkylsulfonyl, S(O).sub.2 NR.sup.6 R.sup.7, OH or one or more halogens; C.sub.2 -C.sub.4 alkenyl optionally substituted with one C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkylthio, CN or one or more halogens; CN; C(O)R.sup.8 ; C(O)OR.sup.9 ; C(O)NR.sup.10 R.sup.11 ; C(R.sup.12).dbd.NOR.sup.13 ; S(O).sub.n R.sup.17 ; S(O).sub.2 NR.sup.18 R.sup.19 ; or halogen;
R.sup.5 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or NR.sup.20 R.sup.21 ;
R.sup.6 is H, C.sub.1 -C.sub.2 alkyl or OCH.sub.3 ;
R.sup.7 is C.sub.1 -C.sub.2 alkyl; or
R.sup.6 and R.sup.7 can be taken together as --(CH.sub.2).sub.3 -- or --(CH.sub.2).sub.4 --;
R.sup.8 is H, C.sub.1 -C.sub.3 alkyl or cyclopropyl;
R.sup.9 is CH.sub.3 ; C.sub.2 -C.sub.3 alkyl optionally substituted with one C.sub.1 -C.sub.2 alkoxy, OH, CN or one or more halogens; C.sub.3 -C.sub.4 alkenyl; or propargyl;
R.sup.10 is H, C.sub.1 -C.sub.3 alkyl or OCH.sub.3 ;
R.sup.11 is C.sub.1 -C.sub.3 alkyl; or
R.sup.10 and R.sup.11 can be taken together as --(CH.sub.2).sub.3 --, --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 -- or --(CH.sub.2).sub.2 O(CH.sub.2).sub.2 --;
R.sup.12 is H, C.sub.1 -C.sub.3 alkyl, allyl, halogen, CN, N.sub.3, C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkylthio or SCN;
R.sup.13 is C.sub.1 -C.sub.3 alkyl or allyl;
R.sup.14 is H or C.sub.1 -C.sub.3 alkyl;
R.sup.15 and R.sup.16 are independently C.sub.1 -C.sub.2 alkyl;
R.sup.17 is C.sub.1 -C.sub.4 alkyl, optionally substituted with one C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkylthio, CN or one or more halogens; C.sub.3 -C.sub.4 alkenyl; or cyclopropylmethyl;
R.sup.18 is H, C.sub.1 -C.sub.3 alkyl or OCH.sub.3 ;
R.sup.19 is H or C.sub.1 -C.sub.2 alkyl; or
R.sup.18 and R.sup.19 can be taken together as --(CH.sub.2).sub.3 --, --(CH.sub.2).sub.4 -- or --(CH.sub.2).sub.5 --;
R.sup.20 and R.sup.21 are independently C.sub.1 -C.sub.2 alkyl; or
R.sup.20 and R.sup.21 can be taken together as --(CH.sub.2).sub.3 --, --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 -- or --(CH.sub.2).sub.2 O(CH.sub.2).sub.2 --;
R.sup.71 is H, halogen or CF.sub.3 ;
R.sup.73 is C.sub.1 -C.sub.4 alkyl optionally substituted with one or more halogens, CN, C.sub.1 -C.sub.2 alkoxy, or C.sub.1 -C.sub.2 alkylthio; C(O)R.sup.74 ; SO.sub.2 R.sup.75 ; C.sub.3 -C.sub.4 alkenyl; or propargyl;
R.sup.74 is C.sub.1 -C.sub.4 alkyl optionally substituted with C.sub.1 -C.sub.2 alkoxy, one or more halogens, or CN; C.sub.3 -C.sub.4 alkenyl; or C.sub.1 -C.sub.3 alkoxy;
R.sup.75 is C.sub.1 -C.sub.3 alkyl or CF.sub.3 ;
m is 0 or 1;
n is 0, 1 or 2;
Q.sup.1 is phenyl, phenyl substituted with one to two groups selected from halogen and CH.sub.3, a fully unsaturated 5- or 6-membered heterocyclic ring containing 1 to 4 heteroatoms selected from 0-1 S, 0-1 O and 0-4 N and a fully unsaturated 5- or 6-membered heterocyclic ring substituted with one to two groups selected from C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, halogen, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.2 haloalkoxy, C.sub.1 -C.sub.3 alkylthio, C.sub.3 -C.sub.4 alkenylthio and C.sub.1 -C.sub.2 haloalkylthio, said Q.sup.1 bound through a carbon atom;
Q.sup.2 is phenyl, a saturated heterocyclic ring containing 1 to 2 heteroatoms selected from 0-2 O and 0-2 S, a partially saturated heterocyclic ring containing 1 to 2 heteroatoms selected from 0-2 O, 0-2 S and 0-2 N, a fully unsaturated 5- or 6-membered heterocyclic ring containing 1 to 4 heteroatoms selected from 0-1 S, 0-1 O and 0-4 N, phenyl substituted with one to two groups selected from halogen and CH.sub.3, a saturated heterocyclic ring containing 1 to 2 heteroatoms selected from 0-2 O and 0-2 S substituted with one to two C.sub.1 -C.sub.3 alkyl groups, a partially saturated heterocyclic ring containing 1 to 2 heteroatoms selected from 0-2 O, 0-2 S and 0-2 N substituted with one to two C.sub.1 -C.sub.3 alkyl groups, and an unsaturated 5- or 6-membered heterocyclic ring containing 1 to 4 heteroatoms selected from 0-1 S, 0-1 O and 0-4 N substituted with one to two groups selected from C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, halogen, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.2 haloalkoxy, C.sub.1 -C.sub.3 alkylthio, C.sub.3 -C.sub.4 alkenylthio and C.sub.1 -C.sub.2 haloalkylthio;
A is ##STR10## X is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, halogen, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino or di(C.sub.1 -C.sub.3 alkyl)amino;
Y is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkylthio, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino, di(C.sub.1 -C.sub.3 alkyl)amino, C.sub.3 -C.sub.4 alkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, C.sub.2 -C.sub.5 alkylthioalkyl, C.sub.2 -C.sub.5 alkylsulfinylalkyl, C.sub.2 -C.sub.5 alkylsulfonylalkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 alkynyl, C.sub.3 -C.sub.5 cycloalkyl, azido, cyano, ##STR11## or N(OCH.sub.3)CH.sub.3 ; p is 2 or 3;
Q.sup.3 and Q.sup.4 are independently O or S;
R.sup.22 is H or C.sub.1 -C.sub.3 alkyl;
R.sup.23 and R.sup.24 are independently C.sub.1 -C.sub.3 alkyl;
Z is CH or N;
Z.sup.1 is CH or N;
Y.sup.1 is O or CH.sub.2 ;
X.sup.1 is CH.sub.3, OCH.sub.3 or OCF.sub.2 H;
X.sup.2 is CH.sub.3, CH.sub.2 CH.sub.3 or CH.sub.2 CF.sub.3 ;
Y.sup.2 is OCH.sub.3, OCH.sub.2 CH.sub.3, SCH.sub.3, SCH.sub.2 CH.sub.3, CH.sub.3 or CH.sub.2 CH.sub.3 ;
X.sup.3 is CH.sub.3 or OCH.sub.3 ;
Y.sup.3 is H or CH.sub.3 ;
X.sup.4 is CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, CH.sub.2 OCH.sub.3 or Cl; and
Y.sup.4 is CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3 or Cl;
and their agriculturally suitable salts;
provided that:
(a) when X and/or Y is C.sub.1 haloalkoxy, then Z is CH;
(b) when m is zero, Q.sup.2 is bound through carbon to the pyrrole ring in J;
(c) when X is F, Cl, Br or I, then Z is CH and Y is OCH.sub.3, OCH.sub.2 CH.sub.3, N(OCH.sub.3)CH.sub.3, NHCH.sub.3, N(CH.sub.3).sub.2 or OCF.sub.2 H;
(d) when W is S, then R is H, A is A-1 and Y is CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, CH.sub.2 OCH.sub.3, CH.sub.2 CH.sub.3, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3, CH(OCH.sub.3).sub.2
or ##STR12## (e) when the total number of carbon atoms of X and Y is greater than four, then the number of carbons of Q.sup.1 and Q.sup.2 for each is less than or equal to eight;
(f) when A is A-2, A-3, A-4, A-5, A-6 or A-7, then R is H;
(g) when J is J-1, A is A-1 and X and/or Y is alkyl, then R.sup.2 is other than CN or NO.sub.2 ;
(h) when J is J-1, A is A-2, A-3 or A-4 and R.sup.1 is C(O)R.sup.5, then R.sup.2 is other than alkyl; and
(i) when J is J-1, A is A-1 and X and/or Y is C.sub.1 haloalkoxy, then R.sup.2 is other than C(O)OR.sup.9.
In the above definitions, the term "alkyl", used either alone or in compound words such as "alkylthio" or "haloalkyl", includes straight chain and branched alkyl, e.g., methyl, ethyl, n-propyl, isopropyl and the different butyl isomers.
Alkoxy includes methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butoxy isomers.
Alkenyl includes straight chain and branched alkenes, e.g., 1-propenyl, 2-propenyl, 3-propenyl and the different butenyl isomers.
Alkylsulfonyl includes methylsulfonyl and ethylsulfonyl.
Alkylthio, etc. are used analogously to the above examples.
Cycloalkyl includes cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
The term "halogen", either alone or in compound words such as "haloalkyl", means fluorine, chlorine, bromine or iodine. Further, when used in compound words such as "haloalkyl" said alkyl may be partially or fully substituted with halogen atoms, which may be the same or different. Examples of haloalkyl include CH.sub.2 CH.sub.2 F, CF.sub.2 CF.sub.3 and CH.sub.2 CHFCl.
The total number of carbon atoms in a substituent group is indicated by the C.sub.i -C.sub.j prefix where i and j are numbers from 1 to 6. For example, C.sub.1 -C.sub.2 alkylsulfonyl would designate methylsulfonyl through ethylsulfonyl; C.sub.2 -C.sub.3 alkoxycarbonyl would designate methoxy and ethoxy attached through a carbonyl radical.
Compounds of the invention preferred for reasons including ease of synthesis and/or greater herbicidal efficacy are:
1. Compounds of Formula I wherein Q.sup.1 is the fully unsaturated substituted or unsubstituted heterocyclic ring, and Q.sup.1 is selected from pyridinyl, pyrimidinyl, thienyl, furanyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, oxazolyl, thiazolyl, imidazolyl or tetrazolyl, and Q.sup.2 is the substituted or unsubstituted heterocyclic ring containing 1 to 2 heteroatoms or the substituted or unsubstituted partially saturated heterocyclic ring containing 1 to 2 heteroatoms and Q.sup.2 is elected from 1,3-dioxolanyl, 1,3-dioxanyl, pyridinyl, pyrimidinyl, thienyl, furanyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, oxazolyl, thiazolyl, imidazolyl or tetrazolyl.
2. Compounds of Preferred 1 wherein:
Q.sup.1 is ##STR13## q is 0 or 1; R.sup.25 and R.sup.26 are independently H, CH.sub.3 or C.sub.1 ;
R.sup.27 and R.sup.28 are independently H, F, or CH.sub.3 ;
R.sup.29 is H, CH.sub.3 or OCH.sub.3 ;
R.sup.30 is H or CH.sub.3 ;
R.sup.31, R.sup.32 and R.sup.33 are independently H, CH.sub.3 or OCH.sub.3 ;
R.sup.34, R.sup.35 and R.sup.36 are independently H, CH.sub.3, CH.sub.2 CH.sub.3, Cl, Br, OCH.sub.3 or OCH.sub.2 CH.sub.3 ;
R.sup.37 is H or C.sub.1 -C.sub.2 alkyl;
R.sup.38 is CH.sub.3 ;
R.sup.39 is H, C.sub.1 -C.sub.2 alkyl, OCH.sub.3 or SCH.sub.3 ;
R.sup.40 is H, CH.sub.3 or CH.sub.2 CH.sub.3 ;
R.sup.41 and R.sup.42 are independently H or CH.sub.3 ;
R.sup.43 is H, CH.sub.3, CH.sub.2 CH.sub.3 or C.sub.3 H.sub.7 ;
W.sup.1 is O or S;
W.sup.2 is O, S or NR.sup.44 ;
R.sup.44 is H or CH.sub.3 ;
Q.sup.2 is ##STR14## r is 0 or 1; R.sup.45 and R.sup.46 are independently H, CH.sub.3 or Cl;
R.sup.47 is H or C.sub.1 -C.sub.3 alkyl;
R.sup.48 is H or CH.sub.3 ;
R.sup.49 and R.sup.50 are independently H or CH.sub.3 ;
R.sup.51 is H, CH.sub.3 or OCH.sub.3 ;
R.sup.52 is H or CH.sub.3 ;
R.sup.53 R.sup.54 and R.sup.55 are independently H, CH.sub.3 or OCH.sub.3 ;
R.sup.56, R.sup.57 and R.sup.58 are independently H, CH.sub.3, CH.sub.2 CH.sub.3, Cl, Br, OCH.sub.3 or OCH.sub.2 CH.sub.3 ;
R.sup.59 is H or C.sub.1 -C.sub.2 alkyl;
R.sup.60 is CH.sub.3 ;
R.sup.61 is H, C.sub.1 -C.sub.2 alkyl, OCH.sub.3 or SCH.sub.3 ;
R.sup.62 is H, CH.sub.3 or CH.sub.2 CH.sub.3 ;
R.sup.63 and R.sup.64 are independently H or CH.sub.3 ;
R.sup.65 is H, CH.sub.3, CH.sub.2 CH.sub.3 or C.sub.3 H.sub.7 ;
W.sup.3 is O or S;
W.sup.4 is O, S or NR.sup.66 ; and
R.sup.66 is H or CH.sub.3.
3. Compounds of Preferred 2 wherein:
W is O;
R.sup.1 is H, C.sub.1 -C.sub.6 alkyl, allyl, CH.sub.2 OCH.sub.3, CH.sub.2 OC.sub.2 H.sub.5, CH.sub.2 SCH.sub.3 phenyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, C(O)OCH.sub.3 or C(O)N(CH.sub.3).sub.2 ;
X is C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, F, Cl, Br, I, OCF.sub.2 H, CH.sub.2 F, CF.sub.3, OCH.sub.2 CH.sub.2 F, OCH.sub.2 CHF.sub.2, OCH.sub.2 CF.sub.3, CH.sub.2 Cl or CH.sub.2 Br; and
Y is H, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, CH.sub.2 OCH.sub.3, CH.sub.2 OCH.sub.2 CH.sub.3, NHCH.sub.3, N(OCH.sub.3)CH.sub.3, N(CH.sub.3).sub.2, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, C(O)R.sup.22, ##STR15## OCF.sub.2 H, SCF.sub.2 H, cyclopropyl, C.tbd.CH or C.tbd.CCH.sub.3.
4. Compounds of Preferred 3 wherein:
R.sup.3 is H, CH.sub.3, Cl or Br; and
R.sup.4 is H, C.sub.1 -C.sub.2 alkyl, CH.sub.2 CN, CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, CH.sub.2 S(O).sub.2 CH.sub.3, Q.sup.2, C(O)R.sup.8, C(O)OR.sup.9, C(O)NR.sup.10 R.sup.11, C(R.sup.12).dbd.NOR.sup.13, C(R.sup.14)(OR.sup.15)(OR.sup.16), S(O).sub.n R.sup.17, S(O).sub.2 NR.sup.18 R.sup.19, F, Cl or Br;
R.sup.8 is H or C.sub.1 -C.sub.2 alkyl;
R.sup.9 is C.sub.1 -C.sub.2 alkyl or CH.sub.2 CH.sub.2 Cl;
R.sup.10 is H or CH.sub.3 ;
R.sup.11 is CH.sub.3 ;
R.sup.12 is H, CH.sub.3, C.sub.2 H.sub.5 or Cl;
R.sup.13 is CH.sub.3 ;
R.sup.14 is H or C.sub.1 -C.sub.2 alkyl;
R.sup.15 and R.sup.16 are CH.sub.3 ;
R.sup.17 is C.sub.1 -C.sub.2 alkyl;
R.sup.18 is H or CH.sub.3 ;
R.sup.19 is CH.sub.3 ; and
n is 0 or 2.
5. Compounds of Preferred 4 wherein:
R.sup.2 is C.sub.1 -C.sub.2 alkyl, CH.sub.2 CN, CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, CH.sub.2 S(O).sub.2 CH.sub.3, Q.sup.2, C(O)R.sup.8, C(O)OR.sup.9, C(O)NR.sup.10 R.sup.11, C(R.sup.12).dbd.NOR.sup.13, C(R.sup.14)(OR.sup.15)(OR.sup.16), S(O).sub.n R.sup.17, S(O).sub.2 NR.sup.18 R.sup.19, F, Cl, Br or OR.sup.73.
6. Compounds of Preferred 5 wherein:
R is H; and
R.sup.71 is H.
7. Compounds of Preferred 6 wherein:
J is J-1.
8. Compounds of Preferred 6 wherein:
J is J-2.
9. Compounds of Preferred 6 wherein:
J is J-3.
10. Compounds of Preferred 7 wherein:
R.sup.2 is C.sub.1 -C.sub.2 alkyl, CH.sub.2 CN, CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, CH.sub.2 S(O).sub.2 CH.sub.3, Q.sup.2, C(O)R.sup.8, C(O)OR.sup.9, C(O)N(CH.sub.3).sub.2, S(O).sub.2 CH.sub.3, S(O).sub.2 C.sub.2 H.sub.5, S(O).sub.2 N(CH.sub.3).sub.2, C.sub.1 -C.sub.2 alkoxy, OC(O)CH.sub.3, or OSO.sub.2 CH.sub.3 ;
R.sup.4 is H, C.sub.1 -C.sub.2 alkyl, CH.sub.2 CN, CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, CH.sub.2 S(O).sub.2 CH.sub.3, Q.sup.2, C(O)R.sup.8, C(O)OR.sup.9, C(O)N(CH.sub.3).sub.2, S(O).sub.2 CH.sub.3, S(O).sub.2 C.sub.2 H.sub.5 or S(O).sub.2 N(CH.sub.3).sub.2 ;
R.sup.8 is C.sub.1 -C.sub.2 alkyl;
R.sup.9 is C.sub.1 -C.sub.2 alkyl;
Q.sup.2 is Q.sup.2 -1, Q.sup.2 -4, Q.sup.2 -5, Q.sup.2 -6, Q.sup.2 -10, Q.sup.2 -11, Q.sup.2 -20 or Q.sup.2 -21;
R.sup.45, R.sup.46, R.sup.49, R.sup.50, R.sup.56, R.sup.57 and R.sup.58 are H;
R.sup.65 is CH.sub.3 ;
W.sup.3 is S; and
r is 0.
11. Compounds of Preferred 8 wherein:
R.sup.2 is C.sub. -C.sub.2 alkyl, CH.sub.2 CN, CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, CH.sub.2 S(O).sub.2 CH.sub.3, Q.sup.2, C(O)R.sup.8, C(O)OR.sup.9, C(O)N(CH.sub.3).sub.2, S(O).sub.2 CH.sub.3, S(O).sub.2 C.sub.2 H.sub.5, S(O).sub.2 N(CH.sub.3).sub.2, C.sub.1 -C.sub.2 alkoxy, OC(O)CH.sub.3, or OSO.sub.2 CH.sub.3 ;
R.sup.4 is H, C.sub.1 -C.sub.2 alkyl, CH.sub.2 CN, CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, CH.sub.2 S(O).sub.2 CH.sub.3, Q.sup.2, C(O)R.sup.8, C(O)OR.sup.9, C(O)N(CH.sub.3).sub.2, S(O).sub.2 CH.sub.3 or S(O).sub.2 N(CH.sub.3).sub.2 ;
R.sup.8 is C.sub.1 -C.sub.2 alkyl;
R.sup.9 is C.sub.1 -C.sub.2 alkyl;
Q.sup.2 is Q.sup.2 -1, Q.sup.2 -4, Q.sup.2 -5, Q.sup.2 -6, Q.sup.2 -10, Q.sup.2 -11, Q.sup.2 -20 or Q.sup.2 -21;
R.sup.45, R.sup.46, R.sup.49, R.sup.50, R.sup.56, R.sup.57 and R.sup.58 are H;
R.sup.65 is CH.sub.3 ;
W.sup.3 is S; and
r is 0.
12. Compounds of Preferred 9 wherein:
R.sup.2 is C.sub.1 -C.sub.2 alkyl, CH.sub.2 CN, CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, CH.sub.2 S(O).sub.2 CH.sub.3, Q.sup.2, C(O)R.sup.8, C(O)OR.sup.9, C(O)N(CH.sub.3).sub.2, S(O).sub.2 CH.sub.3, S(O).sub.2 C.sub.2 H.sub.5, S(O).sub.2 N(CH.sub.3).sub.2, C.sub.1 -C.sub.2 alkoxy, OC(O)CH.sub.3, or OSO.sub.2 CH.sub.3 ;
R.sup.4 is H, C.sub.1 -C.sub.2 alkyl, CH.sub.2 CN, CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, CH.sub.2 S(O).sub.2 CH.sub.3, Q.sup.2, C(O)R.sup.8, C(O)OR.sup.9, C(O)N(CH.sub.3).sub.2, S(O).sub.2 CH.sub.3 or S(O).sub.2 N(CH.sub.3).sub.2 ;
R.sup.8 is C.sub.1 -C.sub.2 alkyl;
R.sup.9 is C.sub.1 -C.sub.2 alkyl;
Q.sup.2 is Q.sup.2 -1, Q.sup.2 -4, Q.sup.2 -5, Q.sup.2 -6, Q.sup.2 -10, Q.sup.2 -11, Q.sup.2 -20 or Q.sup.2 -21;
R.sup.45, R.sup.46, R.sup.49, R.sup.50, R.sup.56, R.sup.57 and R.sup.58 are H;
R.sup.65 is CH.sub.3 ;
W.sup.3 is S; and
r is 0.
13. Compounds of Preferred 10 wherein:
A is A-1;
X is CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, OCH.sub.2 CF.sub.3 or Cl; and
Y is CH.sub.3, OCH.sub.3, NHCH.sub.3 or N(CH.sub.3).sub.2.
14. Compounds of Preferred 11 wherein:
A is A-1;
X is CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, OCH.sub.2 CF.sub.3 or Cl; and
Y is CH.sub.3, OCH.sub.3, NHCH.sub.3 or N(CH.sub.3).sub.2.
15. Compounds of Preferred 12 wherein:
A is A-1;
X is CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, OCH.sub.2 CF.sub.3 or Cl; and
Y is CH.sub.3, OCH.sub.3, NHCH.sub.3 or N(CH.sub.3).sub.2.
Compounds of the invention specifically preferred for reasons of greatest ease of synthesis and/or greatest herbicidal efficacy are:
Methyl 3-[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-amino]sulfonyl]-1-methyl-1H-pyrrole-2-carboxylate;
Methyl 3-[[[[[4-ethoxy-6-(methylamino)-1,3,5-triazin-2-yl]-amino]carbonyl]amino]-sulfonyl]-1-methyl-1H-pyrrole-2-carboxylate;
N.sup.3 -[[(4-ethyl-6-methoxy-1,3,5-triazin-2-yl)-amino]carbonyl]-N.sup.2,N.sup.2,1-trimethyl-1H-pyrrole-2,3-disulfonamide;
N.sup.3 -[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-N.sup.2,N.sup.2,1-trimethyl-1H-pyrrole-2,3-disulfonamide;
Methyl 1-ethyl-2-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl) -amino]-carbonyl]amino]sulfonyl]-1H-pyrrole-3-carboxylate;
2-(ethylsulfonyl)-N-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]-carbonyl]-1-methyl-1H-pyrrole-3-sulfonamide; and
2-[[[[(4,6-dimethoxy-2-pyrimidinyl )amino]carbonyl]-amino]sulfonyl]-N,N,1-trimethyl-1H-pyrrole-3-carboxamide.
The invention also comprises novel compounds, such as the bromopyrrolesulfonamides of Formula II, useful as intermediates to the compounds of Formula I. ##STR16## wherein: R.sup.67 is H, C(CH.sub.3).sub.3 or Si(CH.sub.3).sub.2 C(CH.sub.3).sub.3 ; and
R.sup.72 is H or Si(CH(CH.sub.3).sub.2).sub.3.
Another embodiment of the invention is the process for preparing any of the above compounds, said process comprising reacting
(a) the compounds of Equation 1 in an inert polar aprotic solvent for 5 minutes to 24 hours or more at 20.degree. to 80.degree. C. ##STR17## (b) the compounds of Equation 2 in an inert solvent followed by treatment with aqueous acid ##STR18## (c) the compounds of Equation 3 in an inert solvent for 0.5 to 24 hours ##STR19## (d) the compounds of Equation 4 in an inert solvent at 20.degree. to 80.degree. C. for 0.5 to 24 hours and in the presence of 1 to 1.4 equivalents of a base ##STR20##

DETAILED DESCRIPTION OF THE INVENTION
Synthesis
The sulfonylureas of Formula I can be prepared by a number of methods. These methods are described below along with the appropriate references for greater detail. ##STR21##
One of the methods of synthesis of sulfonylureas of Formula I is depicted in Equation 1 where J, R, and A are as defined above. A sulfonylisocyanate of Formula 2 is contacted with a heterocyclic amine of Formula 3 in an inert polar aprotic solvent, such as acetonitrile, dichloromethane, etc. for periods of several minutes to 24 hours or more, preferably at a temperature in the range of 20.degree. to 80.degree. C. to afford a sulfonylurea of Formula I.
U.S. Pat. Nos. 4,127,405; 4,257,802; and 4,221,585 disclose this equation and are herein incorporated by reference. ##STR22##
Another method of synthesis of compounds of Formula I is depicted in Equation 2 where J, R, and A are as defined previously and R.sup.68 is lower alkyl such as methyl or ethyl. A sulfonamide of Formula 4 is contacted with an alkyl carbamate of Formula 5 in the presence of a trialkylaluminum in an inert solvent such as dichloromethane, 1,2-dichloroethane, etc., and subsequently treated with aqueous acid to afford a sulfonylurea of Formula I. This reaction is taught in European Patent Publication EP-A-83,975 (published Jul. 20, 1983). ##STR23##
Alternatively, compounds of Formula I can be prepared by the method shown in Equation 3 where A, J, and R are as defined previously and Ar represents an aryl group, for example a phenyl group. In this reaction, a sulfonylcarbamate of Formula 6 is contacted with a heterocyclic amine of Formula 3 in an inert solvent such as p-dioxane for a period of 0.5 to 24 hours, as taught in European Patent Publication EP-A-44,807. ##STR24##
A fourth method of preparation for compounds of Formula I is depicted in Equation 4 where A, R, and J are as defined previously and Ar represents an aryl group, for example a phenyl or substituted phenyl group. In this reaction, a sulfonamide of Formula 4 is contacted with a heterocyclic carbamate of Formula 7 in an inert solvent such as p-dioxane or acetonitrile preferably at temperatures in the range of from 20.degree. to 80.degree. C. for periods of 0.5 to 24 hours in the presence of 1 to 1.4 equivalents of a base such as 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). The resultant products are isolated by dilution of the reaction mixture with aqueous acid to afford sulfonylureas of Formula I. The reaction is taught in European Patent Publications EP-A-44,807, and EP-A-85,028.
Intermediate Compounds
Heterocyclic sulfonyl isocyanates of Formula 2 can be prepared by treatment of sulfonamides of Formula 4 by the procedures taught in U.S. Pat. No. 4,127,405. Heterocyclic carbamates of Formula 5 are prepared by procedures taught in European Patent Publication EP-A-83,975.
The sulfonylcarbamates of Formula 6 and heterocyclic carbamates of Formula 7 can be prepared by procedures taught in European Patent Publications EP-A-44,807, EP-A-72,347, EP-A-173,498 and U.S. Pat. No. 4,666,506 and references cited therein.
The intermediate pyrrole sulfonamides of Formula 4 can be prepared by a variety of methods, some of which are described in the sequence of reactions shown in Equations 5 through 24.
The sulfonamides of Formula 4 of this invention where J is J-1, J-2 or J-3 as defined above can be synthesized from the precursor sulfonamides of Formula 8 where J is as defined above and R.sup.69 is a suitable protecting group such as tert-alkyl or trialkylsilyl, by appropriate methods known to one skilled in the art, as depicted in Equation 5. ##STR25##
Sulfonamides of Formula 8 where J is J-2 or J-3, R.sup.1 is as defined above or is a masked synthon thereof, R.sup.2 is as defined above or is a masked synthon thereof, R.sup.69 is as previously defined and R.sup.4 is other than H, X.sup.5 is a suitable leaving group such as but not limited to chloro, bromo, iodo, alkyl- or arylsulfonate, may be prepared by methods similar to the depiction in Equation 6. The general methodology described for the instance when J is J-2 is directly applicable to the instances where J is J-3. Further, the synthetic necessity, and selection of specific masked synthons for specific definitions of R.sup.1 and R.sup.2 are known to one skilled in the art, for the introduction of R.sup.4 into the sulfonamide of Formula 9. ##STR26##
A sulfonamide of Formula 9 can be metalated on carbon using an excess of an organometallic base, preferably an organolithium reagent such as n-butyllithium, n-butyllithium/tetramethylethylenediamine (TMEDA) or lithium diisopropylamide in an inert solvent such as diethyl ether, dimethoxyethane (DME) or tetrahydrofuran (THF), under anhydrous conditions, preferably at a temperature in the range of -100.degree. to -70.degree. C., followed by quenching with the appropriate electrophilic reagent (R.sup.4 --X.sup.5) affording sulfonamide of Formula 8 after standard aqueous workup.
A sulfonamide of Formula 9 where J is J-2, R.sup.1, R.sup.2 and R.sup.69 are as previously defined, X.sup.5 is a suitable leaving group such as but not limited to chloro, bromo, iodo, alkyl- or arylsulfonate, acid chloride or N,N-dialkylamide, can be prepared by methods similar to those depicted in Equation 7. ##STR27##
A sulfonamide of Formula 10 can be metalated on carbon using an excess of organometallic base, as described in J. Org. Chem., vol. 50, p. 4362-4368, (1985) and J. Chem. Soc. Perkin Trans., I., p. 1343, (1982) and the references cited therein, preferably an organolithium reagent such as n-butyllithium, n-butyllithium/tetramethylethylenediamine (TMEDA) or lithium diisopropylamide, in an inert solvent such as diethyl ether, dimethoxyethane (DME) or tetrahydrofuran (THF), under anhydrous conditions, preferably at a temperature in the range of -100.degree. to -70.degree. C., followed by quenching with an appropriate electrophilic reagent (R.sup.2 --X.sup.5) affording sulfonamide of Formula 8 after standard aqueous workup. A sulfonamide of Formula 9 where J is J-3, R.sup.1, R.sup.2 and R.sup.69 are as previously defined, X.sup.5 is a suitable leaving group such as but not limited to chloro, bromo, iodo, alkyl- or arylsulfonate, can be prepared by methods similar to those depicted in Equation 8. ##STR28##
A sulfonamide of Formula 11 can be treated with a base such as an alkali metal alkoxide, hydride or tertiary amine and an appropriate electrophilic reagent (R.sup.1 --X.sup.5) as shown in an inert solvent, preferably a polar aprotic solvent such as dimethylformamide (DMF) to afford a sulfonamide of Formula 9.
Sulfonamides of Formula 10, where J is J-2, R.sup.1, R.sup.69 and X.sup.5 are as previously defined, can be prepared by methods similar to those depicted in Equation 9. ##STR29##
A sulfonamide of Formula 12 is treated with a base such as an alkali metal alkoxide, hydride or tertiary amine and an appropriate electrophilic reagent (R.sup.1 --X.sup.5) as shown in an inert solvent, preferably a polar aprotic solvent such as dimethylformamide (DMF), at a temperature in the range of 20.degree. to 80.degree. C., for a period of 1 to 24 hours to afford a sulfonamide of Formula 10.
Pyrrole sulfonamides of Formula 12, where R.sup.69 is a suitable protecting group as defined above are available from the corresponding bromopyrroles 13 as outlined in Equation 10, where R.sup.70 is lower alkyl, such as isopropyl. ##STR30##
N-Silyl-protected pyrrole 13 where R.sup.70 is preferably an isopropyl group, is treated with an alkyllithium reagent such as n-butyllithium as described in Chem. Ber., Vol 122 p.169 (1989), and references cited therein. The resultant metalated species is treated with sulfur dioxide to afford sulfinate salt 14 which can be converted to sulfonamide 15 by any of several known methods, for example treatment with N-chlorosuccinimide followed by amination with an appropriate primary amine as disclosed in U.S. Pat. No. 4,481,029. The N-silyl group is then removed, most conveniently with an alkali fluoride or quaternary ammonium fluoride salt to afford pyrrole-3-sulfonamide 12.
Sulfonamides of Formula 11, where J is J-3, R.sup.2, R.sup.69 and X.sup.5 are as previously defined, can be prepared by methods similar to those depicted in Equation 11, where R.sup.70 is lower alkyl, such as isopropyl. ##STR31##
A sulfonamide of Formula 16 undergoes metal-halogen exchange on carbon using an excess of organometallic base, as described in J. Org. Chem., vol. 50, p. 4362-4368, (1985) and J. Chem. Soc. Perkin Trans., I, p. 1343, (1982) and the references cited therein, preferably an organolithium reagent such as n-butyllithium, n-butyllithium/tetramethylethylenediamine (TMEDA) in an inert solvent such as diethyl ether, dimethoxyethane (DME) or tetrahydrofuran (THF), under anhydrous conditions, preferably at a temperature in the range of -100.degree. to -70.degree. C., followed by quenching with an appropriate electrophilic reagent (R.sup.2 --X.sup.5) affording intermediate sulfonamide of Formula 17. The N-silyl group is then removed, most conveniently with an alkali fluoride or quaternary ammonium fluoride salt to afford sulfonamide 11.
A pyrrole sulfonamide of Formula 16, where R.sup.69 is a suitable protecting group as defined above can be prepared from the corresponding bromopyrrole 13 as outlined in Equation 12, where R.sup.70 is lower alkyl, such as isopropyl. ##STR32##
N-silyl-protected pyrrole 13 where R.sup.70 is preferably an isopropyl group, is treated with an alkyllithium reagent such as n-butyllithium as described in Chem. Ber., Vol. 122, p. 169 (1989), and references cited therein. The resultant metalated species is treated with sulfur dioxide to afford sulfinate salt 18 which can be converted to sulfonamide 19 by any of several known methods, for example treatment with N-chlorosuccinimide in a solvent such as acetic acid, methylene chloride/H.sub.2 O, 1,1,2-trichlorotrifluoroethene/H.sub.2 O at a temperature from 0.degree. C. to ambient temperature followed by amination with an appropriate primary amine as disclosed in U.S. Pat. No. 4,481,029. Sulfonamide 19 can be converted to a compound of Formula 16 by treatment with N-bromosuccinimide in an inert solvent such as tetrahydrofuran (THF), under anhydrous conditions, preferably at a temperature in the range of -100.degree. to -70.degree. C. as described in J. Org. Chem., Vol. 55, No. 26, pp. 637-28 (1990) and the references cited therein.
In the cases where R.sup.2 is not directly obtainable as an electrophilic reagent (R.sup.2 --X5), wherein R.sup.2 is defined as --S(O).sub.2 NR.sup.18 R.sup.19, --CONR.sup.10 R.sup.11, C(R.sup.12).dbd.NOR.sup.13, --S(O).sub.n --R.sup.17, C(O)R.sup.8, (CH.sub.2 .sub.m --Q.sup.2 or --CN the desired compounds can be obtained through a series of functional group transformations known to one skilled in the art. The general methodology described for the instance when J is J-2 is directly applicable to the instances where J is J-1 or J-3 with modifications known to one skilled in the art. Therefore, only the instances where J is J-2, R.sup.1 is CH.sub.3 and R.sup.69 is a suitable protecting group such as tert-alkyl or trialkylsilyl will be described in Equations 13 to 19.
Equation 13 depicts a sequence of reactions whereby one can obtain a sulfonamide of Formula 21 where J is J-2, R.sup.1 and R.sup.69 are as previously defined and R.sup.2 is --S(O).sub.2 NR.sup.18 R.sup.19 wherein R.sup.18 and R.sup.19 are as defined above. ##STR33##
A precursor sulfonamide of Formula 10 can be metalated on carbon using an excess of organometallic base, similar to that described in J. Org. Chem., vol. 50, p. 4362-4368, (1985) and J. Chem. Soc. Perkin Trans., I, p. 1343, (1982) and the references cited therein, preferably an organolithium reagent such as n-butyllithium, n-butyllithium/tetramethylethylenediamine (TMEDA) or lithium diisopropylamide, in an inert solvent such as diethyl ether, dimethoxyethane (DME) or tetrahydrofuran (THF), under anhydrous conditions, preferably at a temperature in the range of -100.degree. to -70.degree. C. The resultant metalated species is treated with sulfur dioxide to afford sulfinate salt 20 which can be converted to sulfonamide 21 by any of several known methods, for example treatment with N-chlorosuccinimide followed by amination with an appropriate amine in an analogous manner to that disclosed in U.S. Pat. No. 4,481,029.
In an analogous manner Equation 14 outlines a sequence wherein one can prepare a sulfonamide of Formula 22 where J is J-2, R.sup.1 and R.sup.69 are as previously defined and R.sup.2 is --C(O)NR.sup.10 R.sup.11. ##STR34##
A precursor sulfonamide of Formula 9 where R.sup.2 is defined for example as --C(O)OR.sup.9 where R.sup.9 is preferably methyl or ethyl, can be converted to amide 22 by any of several known methods, for example contacting the ester with an appropriate amine in the presence of an organometallic base in an analogous manner to that disclosed in Tetrahedron Letters, No. 21, p. 1791, (1970).
Equation 15 outlines a sequence whereby one can prepare a sulfonamide of Formula 23 where J is J-2, R.sup.1 and R.sup.69 are as previously defined and R.sup.2 is --CN. ##STR35##
A precursor sulfonamide of Formula 9 where R.sup.2 is defined for example as --CONH.sub.2 can be converted to nitrile 23 by any of several known methods, for example contacting the amide with triphenylphosphine and CCl.sub.4 in an inert solvent, in an analogous manner to that disclosed in Tetrahedron Letters, No. 21, p. 4383, (1970), or by dehydration with thionyl chloride as described in Org. Syn., coll. vol. IV, p. 436, (1963).
Equation 16 depicts a sequence whereby one can prepare a sulfonamide of Formula 25 where J is J-2, R.sup.1 and R.sup.69 are as previously defined, R.sup.2 is (CH.sub.2).sub.m --Q.sup.2, Q.sup.2 is Q.sup.2 -1, Q.sup.2 -4, Q.sup.2 -5, Q.sup.2 -6, Q.sup.2 -7, Q.sup.2 -8, Q.sup.2 -9, Q.sup.2 -10 or Q.sup.2 -11, r is 0, m is 0 and M is ZnCl.sub.x, ZnBr.sub.x, or B(OH).sub.2. ##STR36##
A sulfonamide of Formula 10 can be metalated on carbon using an excess of organometallic base, similar to that described in J. Org. Chem., vol. 50, p. 4362-4368, (1985) and J. Chem. Soc. Perkin Trans., I, p. 1343, (1982) and the references cited therein, preferably an organolithium reagent such as n-butyllithium, n-butyllithium/tetramethylethylene-diamine (TMEDA) or lithium diisopropylamide, in an inert solvent such as diethyl ether, dimethoxyethane (DME) or tetrahydrofuran (THF), under anhydrous conditions, preferably at a temperature in the range of -100.degree. to -70.degree. C. The metalated species can be transmetalated with anhydrous zinc chloride, by methods similar to those described in Tetrahedron Letters, Vol. 29, No. 39, pp. 5013-5016, (1988). The transmetalated species 24 can be coupled to an arylhalide substrate, for instance 2-bromopyridine, in the presence of excess zinc chloride and a palladium catalyst to afford the biaryl species of Formula 25. Alternatively, the metalated species can be quenched with an alkyl borate, for instance trimethylborate affording the corresponding 2-boronic acid species 24 upon hydrolysis. The pyrrole boronic acid species can be coupled to an arylhalide substrate by methods similar to those described in Tetrahedron Letters, vol. 26, No. 49, pp. 5997-6000, (1985) and Tetrahedron Letters, vol. 29, No. 43, p. 5459-5462, (1988) and the references cited therein, for instance 2-bromopyridine in the presence of a palladium catalyst and a base, in an inert solvent such as toluene or dimethoxyethane (DME), at reflux temperature for periods of 1 to 24 hours affording the biaryl species of Formula 25.
Equation 17 outlines a sequence whereby one can prepare a sulfonamide of Formula 27 where J is J-2, R.sup.1 and R.sup.69 are as previously defined, R.sup.2 is --C(R.sup.12).dbd.NOR.sup.13, R.sup.12 is H and R.sup.13 is as previously defined. ##STR37##
A sulfonamide of Formula 10 can be metalated on carbon using an excess of organometallic base, similar to that described in J. Org. Chem., vol. 50, p. 4362-4368, (1985) and J. Chem. Soc. Perkin Trans., I, p. 1343, (1982) and the references cited therein, preferably an organolithium reagent such as n-butyllithium, n-butyllithium/tetramethylethylenediamine (TMEDA) or lithium diisopropylamide, in an inert solvent such as diethyl ether, dimethoxyethane (DME) or tetrahydrofuran (THF), under anhydrous conditions, preferably at a temperature in the range of -100.degree. to -70.degree. C. The metalated species, quenched with dimethylformamide (DMF) affords the corresponding pyrrole-2-aldehyde 26 following aqueous workup. The aldehyde species 26 is contacted with an alkoxy amine (H.sub.2 -OR.sup.13), for instance methoxylamine hydrochloride in the presence of a base, for example sodium acetate, in an inert solvent such as acetone, tetrahydrofuran, dioxane or methanol. The reaction is carried out at temperatures in the range of 20.degree. C. to reflux for a period of 1 to 24 hours and optionally in the presence of a phase transfer catalyst such as a crown ether.
Equation 18 depicts a sequence whereby one can prepare a sulfonamide of Formula 29 where J is J-2, R.sup.1 and R.sup.69 are as previously defined and R.sup.2 is --C(O)R.sup.8 where R.sup.8 is as defined above. ##STR38##
A sulfonamide of Formula 10 can be metalated on carbon using an excess of organometallic base, similar to that described in J. Org. Chem., vol. 50, p. 4362-4368, (1985) and J. Chem. Soc. Perkin Trans., I, p. 1343, (1982) and the references cited therein, preferably an organolithium reagent such as n-butyllithium, n-butyllithium/tetramethylethylenediamine (TMEDA) or lithium diisopropylamide, in an inert solvent such as diethyl ether, dimethoxyethane (DME) or tetrahydrofuran (THF), under anhydrous conditions, preferably at a temperature in the range of -100.degree. to -70.degree. C. The metalated species, quenched with an aldehyde (R.sup.8 -CHO) affords the alcohol 28 following aqueous workup. Alcohol 28 can be oxidized to a ketone of Formula 29 by contact with one of several oxidants known to one skilled in the art, for example tetra-n-propylammonium perruthenate/N-methylmorpholine N-oxide as described in Aldrichimica Acta, Vol. 23, No. 1, p. 13-17, (1990) and the references cited therein.
Equation 19 outlines a sequence whereby one can prepare a sulfonamide of Formula 31 where J is J-2, R.sup.1 and R.sup.69 are as previously defined and R.sup.2 is --S(O).sub.n --R.sup.17, where R.sup.17 is as defined above and n is 1 or 2. ##STR39##
A sulfonamide of Formula 10 can be metalated on carbon using an excess of organometallic base, similar to that described in J. Org. Chem., vol. 50, p. 4362-4368, (1985) and J. Chem. Soc. Perkin Trans., I, p. 1343, (1982) and the references cited therein, preferably an organolithium reagent such as n-butyllithium, n-butyllithium/tetramethylethylenediamine (TMEDA) or lithium diisopropylamide, in an inert solvent such as diethyl ether, dimethoxyethane (DME) or tetrahydrofuran (THF), under anhydrous conditions, preferably at a temperature in the range of -100.degree. to -70.degree. C. The metalated species, quenched with an appropriate disulfide (R.sup.17 -S-S-R.sup.17) affords thioether 30 following aqueous workup. The thioether can be oxidized selectively to the corresponding sulfoxide or sulfone of Formula 31 by contact with one of several suitable oxidants such as a peroxy acid or hydrogen peroxide.
Pyrrole sulfonamide precursors of Formula 36 where J is J-1, R.sup.3 is H or alkyl and R.sup.69 is a trialkylsilyl protecting group can be prepared from the corresponding N-substituted pyrrole 32 as outlined in Equation 20. ##STR40##
Pyrroles of Formula 32 are generally known in the art or can be prepared by a variety of known alkylation or acylation procedures such as those reviewed in "Pyrroles", R. Alan Jones, Ed., "The Chemistry of Heterocyclic Compounds", Vol. 48, Part 1 (John Wiley & Sons, Inc., 1990, New York) p. 397. Metalation of pyrroles 32 is likewise known to produce reactive 2-lithio intermediates as described in Synthetic Communications, Vol. 12, p. 231 (1982) and in J. Org. Chem., Vol. 46, p. 157 (1981) and references cited therein. Treatment of these reactive metalated species with sulfur dioxide affords sulfinate salts 33. These can be converted to sulfonamides 34 by methods described above, or directly by treatment with hydroxylamine-O-sulfonic acid in aqueous media as described in Synthesis, p. 1031 (1986). Treatment of sulfonamides 34 with a base and a trialkylsilyl chloride such as t-butyldimethylsilyl chloride affords the protected sulfonamides 35. Metalation of 35 with two equivalents of an organometallic base such as n-butyllithium, lithium diisopropylamide or lithium 2,2,6,6-tetramethylpiperidide (LTMP) and quenching with an appropriate electrophilic reagent R.sup.2 X.sup.5 affords substituted sulfonamides 36. Directed metalations of this type on 1,2-disubstituted pyrroles have been described in J. Org. Chem., Vol. 50, p. 4362 (1985) and J. Chem. Soc. Perkin Trans. I, p. 1343 (1982) and references cited therein. When 32 contains R.sup.1 groups that are incompatible with strongly basic conditions of the subsequent reactions, such as when R.sup.1 is CO.sub.2 CH.sub.3 or C(O)CH.sub.3, a suitable protecting group in place of R.sup.1 can be substituted such as those described in J. Org. Chem., Vol 46, p. 157 (1981), ibid., p. 3760, and in Tetrahedron, Vol. 42, p. 3723 (1986). This protecting group can be removed at a suitable point in the synthesis, such as after the synthesis of sulfonamide 36, and replaced with the appropriate R.sup.1 group by standard alkylation or acylation methods as described above. Intermediates 34 or 35 where R.sup.3 is hydrogen can be directly halogenated to afford the corresponding substituted sulfonamides 34 or 35 where R.sup.3 is halogen. Conversion of these intermediates to sulfonamides of Formula 36 where R.sup.3 is halogen is best carried out using a substituted lithium amide base, such as lithium diisopropylamide, followed by treatment with an electrophillic reagent as described above.
Intermediate sulfonamides of Formula 38 where J is J-1 and R.sup.71 is other than H can be prepared as depicted in Equation 21 from the corresponding sulfonamides 36, where X.sup.6 is chloro, bromo or iodo. ##STR41##
Treatment of sulfonamides with a halogenating agent affords sulfonamides 37 where X.sup.6 is chloro, bromo, or iodo. Further treatment of 37 where X.sup.6 is bromo or iodo with an alkyllithium in an inert solvent followed by an alkyl halide affords sulfonamides 38 where R.sup.71 is lower alkyl. Likewise treatment of 37 with an alkyllithium reagent and subsequently with a mild fluorinating agent such as that described in J. Am. Chem. Soc., Vol. 106, p. 452 (1984) affords sulfonamides 38 wherein R.sup.71 is a fluoro substituent. Compounds of 37 where X.sup.6 is bromo or iodo to 38 where R.sup.71 is CF.sub.3 can be accomplished by first treatment with an alkyllithium reagent followed by quenching with carbon dioxide to afford an intermediate acid 37 where R.sup.71 is COOH, and subsequent reaction with sulfur tetrafluoride or the like.
An intermediate pyrrole of Formula 40 where R.sup.1 is defined as Q.sup.1 above, can be prepared by the method outlined in Equation 22. ##STR42##
Amine 39 can be condensed with 2,5-dimethoxy tetrahydrofuran by the method described in Org. Syn., coll. vol. V, pp. 716-717, affording pyrrole 40.
Intermediate sulfonamides of Formula 44 where J is J-1, R.sup.3 is H, R.sup.1 is Q.sup.1 and R.sup.69 is a trialkylsilyl protective group can be prepared from the corresponding N-substituted pyrrole 40 as depicted in Equation 23. ##STR43##
Pyrroles of Formula 40 can be metalated on carbon using an organometallic base, as described in Org. React., vol. 26, p. 21 (1979) and the references cited therein, preferably using an organolithium reagent such as n-butyllithium, lithium diisopropyl amide, or n-butyllithium/tetramethylethylenediamine. Treatment of the metalated species with sulfur dioxide affords the sulfinate salts 41. These can be converted to sulfonamides 42 by methods described above. Treatment of 42 with a base and a trialkylsilyl chloride affords protected sulfonamides 43. Metalation of 43 with two equivalents of an organometallic base as described above, and quenching with an appropriate electrophilic reagent R.sup.2 X.sup.5 affords substituted sulfonamides 44.
Intermediate sulfonamides of Formula 49 where J is J-2, R.sup.4 is H, R.sup.1 is Q.sup.1 and R.sup.69 is a trialkylsilyl protecting group can be prepared from the corresponding N-substituted pyrrole 40 as outlined in Equation 24. ##STR44##
Pyrroles of Formula 40 can be brominated by methods similar to those reviewed in "Pyrroles," R. Alan Jones, Ed., "The Chemistry of Heterocyclic Compounds," vol. 48, Prt. 1 (John Wiley & Sons, Inc., 1990, New York) p. 372, affording 3-bromo pyrroles of Formula 45. Pyrroles of Formula 45 can undergo metal halogen exchange by the methods described above with an organometallic base, preferably an organolithium reagent. Treatment of the metalated species with sulfur dioxide affords sulfinite salts 46. These salts can be converted to sulfonamides 47 by methods described above. Treatment of 47 with a base and a trialkylsilyl chloride affords protected sulfonamides Metalation of 48 with two equivalents of an organometallic base such as n-butyllithium, lithium diisopropyl amide or n-butyllithium/tetramethylethylenediamine and quenching with an appropriate electrophilic reagent R.sup.2 X.sup.5 affords substituted sulfonamides 49. Directed metalation of 1,3-disubstituted pyrroles is described above.
Compounds of Formula 53 can be prepared by the method outlined in Equation 25. ##STR45##
Compound 50, prepared by the method described in J., Org. Chem., 55, 6317 (1990), is treated with 1 equivalent of an alkyllithium reagent such as n-butyllithium, and the resulting metalated species is treated with sulfur dioxide to obtain sulfinate salt 51 which can be converted to sulfonamide 52 by any of several known methods. For example treatment with N-chlorosuccinimide in acetic acid, followed by amination. The sulfonamide 52 is treated with a base such as an alkali metal alkoxide, hydride or tertiary amine and an appropriate electrophilic reagent (R.sup.1 --X.sup.5) as shown in an inert solvent, to give a sulfonamide of Formula 53.
Sulfonamides of Formula 54 or 55 can be prepared by methods similar to those depicted in Equation 26. ##STR46##
Sulfonamide 53 can be treated with cupric cyanide in a polar aprotic solvent preferably DMF, at a temperature in the range of 100.degree. to 55.degree. C. For a period of 6 to 28 hours to afford a sulfonamide of Formula 54. Treatment of sulfonamide 53 with an aryl boronic acid in the presence of a palladium (O) catalyst, such as tetrakis (triphenylphosphine) palladium, and an inorganic base, such as sodium carbonate, by methods similar to those described in Synthetic Comm., 11 513 (1981), affords sulfonamides of Formula 55.
Sulfonamides of Formula 11 may also be prepared by the method depicted in Equation 27. ##STR47##
N-Silyl-protected pyrrole 50 where R.sup.70 is preferably an isopropyl group, is treated with an alkyllithium reagent such as n-butyllithium, and the resulting metalated species is treated with an appropriate electrophilic reagent (R.sup.2 --X.sup.5) as shown in an inert solvent to afford compound 56. Similar treatment of compound 56 with an alkyllithium reagent such as n-butyllithium and quenching of the metalated species thus formed with sulfur dioxide affords the sulfinate salt 57 which can be converted to sulfonamide 11 by any of several known methods as described above.
The synthesis of heterocyclic amine derivatives such as those depicted in Formulas 3, 5 and 7 are either known, or can be prepared by obvious methods known to one skilled in the art. For a review of the synthesis and reactions of 2-amino- and 2-methylaminopyrimidines see The Chemistry of Heterocylic Compounds, vol 16, Wiley-Interscience, New York (1962). For a review of the synthesis and reactions of 2-amino- and 2-methylamino-s-triazines, see The Chemistry of Heterocyclic Compounds, vol 13, Wiley-Interscience, New York (1959), F. C. Schaefer U.S. Pat. No. 3,154,537 and F. C. Schaefer and K. R. Huffman J. Org. Chem., 28, 1812 (1963). J. Chem., Soc., 2031 (1966), EP-A-173,498 and U.S. Pat. No. 4,666,506 describes further methods. The synthesis of the bicyclic amines of Formula 3 where A is A-2 and A-3 is taught in U.S. Pat. No. 4,339,267. The synthesis of bicyclic amines of Formula 3, where A is A-4 is taught in European Patent Publication EP-A-46,667.
The synthesis of compounds of Formula 3 where A is A-5 are described European Patent Publication EP-A-73,562. The synthesis of compounds of Formula 3 where A is A-6 are described European Patent Publication EP-A-94,260.
The compounds of Formula 3 where A is A-7 can be prepared by methods taught in EP-A-125,864 (published Nov. 21, 1984) or by suitable modifications that would be obvious to one skilled in the art.
The amines of Formula A where X.sup.1 is OCF.sub.2 H can be prepared by methods taught in EP-A-72,347, or by suitable modifications that would be obvious to one skilled in the art.
The pyrimidines of Formula 3 where A is A-1 (Z.dbd.CH) and where Y is ##STR48## can be prepared according to the method taught in European Patent Publication EP-A-84,224 or suitable modifications thereof known to one skilled in the art.
Agricultural suitable salts of compounds of Formula I are also useful herbicides and can be prepared in a number of ways known to the art. For example, metal salts can be made by contacting compounds of Formula I with a solution of an alkali or alkaline earth metal salt having a sufficiently basic anion (e.g., hydroxide, alkoxide, carbonate or hydroxides). Quaternary amine salts can be made by similar techniques.
Salts of compounds of Formula I can also be prepared by exchange of one cation for another. Cationic exchange can be effected by direct contact of an aqueous solution of a salt of a compound of Formula I (e.g., alkali or quaternary amine salt) with a solution containing the cation to be exchanged. This method is most effective when the desired salt containing the exchanged cation is insoluble in water and can be separated by filtration.
Exchange may also be effected by passing an aqueous solution of a salt of a compound of Formula I (e.g., alkali metal or quaternary amine salt) through a column packed with a cation exchange resin containing the cation to be exchanged for that of the original salt and the desired product is eluted from the column. This method is particularly useful when the desired salt is water-soluble, e.g., potassium, sodium or calcium salt.
Acid addition salts useful in this invention, can be obtained by reacting a compound of Formula I with a suitable acid, e.g., p-toluenesulfonic acid, trichloroacetic acid or the like.
The preparation of the compounds of this invention is further illustrated by the following specific examples. Abbreviations for nuclear magnetic resonance (NMR) signals are: s=singlet, bs=broad singlet, d=doublet, t=triplet, m=multiplet, q=quartet, and peak positions are reported as parts per million downfield from internal tetramethylsilane. Infrared (IR) peak positions are given in reciprocal centimeters (cm.sup.-1) and sh denotes shoulder.
EXAMPLE 1
N-(1,1-Dimethylethyl)-1-[tris(1-methylethyl)silyl]-1H-3-sulfonamide
A solution of 30.25 g (0.10 mol) of 3-bromo-N-triisopropylsilylpyrrole in 500 mL of anhydrous tetrahydrofuran (THF) under nitrogen atmosphere was cooled to -78.degree. C. The colorless solution was treated with 44 mL of 2.38M n-butyllithium in hexanes (0.105 mol) dropwise at such a rate as to keep the temperature below -65.degree. C. After ca. 1 hour at -78.degree. C., liquified sulfur dioxide was added (25.8 ml, 0.6 mol). The amber solution was warmed to room temperature and stirred for ca. 1 hour. The THF was removed under reduced pressure. The resulting amber oil was dissolved in 500 ml, glacial acetic acid, cooled to 20.degree. C. and then treated with 13.35 g (0.1 mol) of N-chlorosuccinimide. After ca. 1 hour at room temperature the acetic acid was evaporated at reduced pressure and the residue was dissolved in ethyl acetate. This solution was washed successively with water, NaHCO.sub.3 solution, brine, then dried (MgSO.sub.4) and evaporated in vacuo. The resulting amber oil residue was dissolved in methylene chloride 500 mL, cooled to -20.degree. C. and treated with t-butylamine. The resulting dark brown turbid solution was allowed to warm to room temperature and stir overnight ca. 16 hours. The solution was washed with 1N HCl, dried (MgSO.sub.4) and evaporated to a dark oil. Chromatography on silica gel (20% ethyl acetate/80% hexanes) afforded 10.48 g of the title compound as a cream colored solid, m.p. 103.degree.-104.degree. C.
.sup.1 H NMR (CDCl.sub.3, 200 MHz.) .delta.: 7.28(d,1H), 6.74(m,1H), 6.56(bs,1H), 4.39(bs,1H), 1.45(m,3H), 1.23(s,9H), 1.08(d,18H).
EXAMPLE 2
N-(1,1-Dimethylethyl)-1H-pyrrole-3-sulfonamide
A solution of N-(1,1-dimethylethyl)-1-[tris-(1-methylethyl)silyl]-1H-3-sulfonamide (10.48 g, 0.0293 mol) in 100 mL, diethyl ether under a nitrogen atmosphere was treated with tetrabutylammoniumfluoridehydrate 10.16 g (0.0388 mol) followed by 1.8 mL of glacial acetic acid. After stirring ca. 1.5 hours at room temperature, the reaction mixture was filtered through silica with diethyl ether rinse. The filtrate was concentrated in vacuo affording 4.1 g of the title compound as a white solid, m.p. 146.degree.-148.degree. C.
.sup.1 H NMR (CDCl.sub.3, 200 MHz.) .delta.: 8.58(bs,1H), 7.32(s,1H), 6.79(d,1H), 6.52(d,1H), 4.34(bs,1H), 1.26(s,9H).
EXAMPLE 3
N-(1,1-Dimethylethyl)-1-methyl-1-pyrrole-3-sulfonamide
A solution of N-(1,1-dimethylethyl)-1H-pyrrole-3-sulfonamide 9 g (0.044 mol) in 90 mL N,N-dimethylforamide was cooled to 15.degree. C. under a nitrogen atmosphere. To this was added 3.2 ml, (0.053 mol) of methyl iodide followed by 5.43 g (0.048 mol) of potassium t-butoxide. The mixture was warmed at ca. 60.degree. C. for 2 hours then allowed to cool to room temperature and stirred for ca. 2 hours. The reaction mixture was diluted with ethyl acetate, washed three times with 1N HCl, once with brine, dried (MgSO.sub.4) and evaporated to an oily solid which was triturated with 5% diethyl ether/95% hexanes affording 6 g of the title compound as a beige solid, m.p. 134.degree.-135.degree. C.
.sup.1 H NMR (CDCl.sub.3, 200 MHz.) .delta.: 7.11(s,1H), 6.59(d,1H), 6.41(d,1H), 4.32(bs,1H), 3.67(s,3H), 1.26(s,9H).
EXAMPLE 4
Methyl 3-[[(1,1-dimethylethyl)amino]sulfonyl]-1-methyl-1H-pyrrole-2-carboxylate
To a solution of 1 g (4.62 mmol) of N-(1,1-dimethylethyl)-1-methyl-1H-pyrrole-3-sulfonamide in 150 ml, THF under a nitrogen atmosphere cooled to -78.degree. C. was added dropwise at such a rate as to keep the temperature below -65.degree. C. 4.1 mL (9.48 mmol) 2.32M n-butyllithium in hexanes. The resulting amber turbid solution was stirred at -78.degree. C. for ca. 30 minutes. Methyl chloroformate (0.37 mL, 4.86 mmol) was added in one portion and the resulting gold reaction mixture was allowed to warm to room temperature and stirred for ca. 1.5 hours. The gold reaction mixture was cooled to 0.degree. C. and acidified with 1N HCl. The THF phase was separated washed with brine, dried (MgSO.sub.4) and concentrated to an amber oil. The NMR of the crude reaction product was consistent with the title compound, additionally the NMR indicated that a trace of the starting material was also present. The crude material was combined with the product from a similar reaction run on the scale described below and chromatographed to give the title compound.
To a solution of 5 g (23 mmol) of N-(1,1-dimethylethyl)-1-methyl-1H-pyrrole-3-sulfonamide in 150 mL THF under nitrogen atmosphere cooled to -78.degree. C. was added dropwise, at such a rate as to keep the temperature below -65.degree. C., 20 mL (47.4 mmol) 2.32M n-butyllithium in hexanes. The resulting amber turbid solution was stirred at -78.degree. C. for ca. 30 minutes. 1.87 mL (24.3 mmol) of methyl chloroformate was add in one portion and the resulting gold reaction mixture was allowed to warm to room temperature and stir for ca. 1.5 hours. The gold reaction mixture was cooled to 0.degree. C. and acidified with 1N HCl. The THF phase was separated, washed with brine, dried (MgSO.sub.4) and concentrated to an amber oil. The oil was combined with the crude product from the previous example and chromatographed on silica (30% ethyl acetate/70% hexanes) affording 3.53 g of the title compound as a solid.
.sup.1 H NMR (CDCl.sub.3, 200 MHz.) .delta.: 6.71(dd,2H), 5.72(bs,1H), 3.95(s,3H), 3.91(s,3H), 1.24(s,9H).
EXAMPLE 5
Methyl 3-(aminosulfonyl)-1-methyl-1H-pyrrole-2-carboxylate
To a solution of 3.53 g of methyl 3-[[(1,1-dimethylethyl)amino]sulfonyl]-1-methyl-1H-pyrrole-2-carboxylate in 40 mL of methylene chloride under an nitrogen atmosphere was added 80 ml, of trifluoroacetic acid (TFA). The gold solution was stirred at room temperature overnight ca. 16 hours. The gold solution was concentrated to an oily residue. Diethyl ether was added to the residue and removed by evaporation to remove residual TFA. The resulting solid was suspended in diethyl ether and filtered affording the title compound as a tan solid, m.p. 105.degree.-107.degree. C.
.sup.1 H NMR (Acetone-d.sub.6, 200 MHz.) .delta.: 7.01(d,1H), 6.51(d,1H), 6.28(bs,2H), 3.95(s,3H), 3.93(s,3H).
EXAMPLE 6
Methyl 3-[[[[(4,6-dimethoxy-2-pyrimidinyl)-amino]carbonyl]amino]sulfonyl]-1-methyl-1H-pyrrole-2-carboxylate
0.22 g (1 mmol) of methyl 3-(aminosulfonyl)-1-methyl-1H-pyrrole -2-carboxylate and 0.28 g (1 mmol) of phenyl (4,6-dimethoxy-2-pyrimidinyl) carbamate were combined in 4 mL of acetonitrile, 0.2 mL (1.33 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) was added and the resulting amber reaction mixture was allowed to stand at room temperature overnight ca. 16 hours. The reaction mixture was diluted with 6 mL of water and ca. 2 mL of shaved ice, acidified with cone. HCl (ca. 8 drops) to pH 4. The resulting precipitate was filtered washed with water followed by diethyl ether and air dried affording 0.2 g of the title compound as a solid m.p. 182.5.degree.-186.5.degree. C.
.sup.1 H NMR (Me.sub.2 SO-d.sub.6, 200 MHz.) .delta.: 12.45(bs,1H), 10.45(bs,1H), 7.21(d,1H), 6.65(d,1H), 6.01(s,1H), 3.93(s,6H), 3.85(s,3H), 3.7(s,3H).
EXAMPLE 7
N-(1,1-Dimethylethyl)-1-methyl-2-(methylthio)-1H-pyrrole-3-sulfonamide
To a solution of 6.48 g (30 mmol) of N-(1,1-dimethylethyl)-1-methyl-1H-pyrrole-3-sulfonamide in 150 mL THF under nitrogen atmosphere cooled to -78.degree. C. was added dropwise at such a rate as to keep the temperature below -65.degree. C. 25.52 mL (61.5 mmol) 2.41M n-butyllithium in hexanes. The reaction was stirred at -78.degree. C. for ca. 30 minutes. To the reaction mixture was added 2.97 mL (33 mmol) of dimethyldisulfide in one portion and the resulting reaction mixture was allowed to warm to room temperature and stir for ca. 1.5 hours. The reaction mixture was cooled to 0.degree. C. and acidified with 1N HCl. The THF phase was separated washed with brine, dried (MgSO.sub.4) and concentrated in vacuo. The crude residue was chromatographed on silica (20% ethyl acetate/80% hexanes) affording 4.63 g of the title compound as an off white solid, m.p. 116.degree.-119.degree. C.
.sup.1 H NMR (CDCl.sub.3, 200 MHz.) .delta.: 6.72(d,1H), 6.58(d,1H), 4.96(bs,1H), 3.74(s,3H), 2.35(s,3H), 1.23(s,9H).
EXAMPLE 8
1-Methyl-2-(methylthio)-1H-pyrrole-3-sulfonamide
To a solution of 4.63 g (17.66 mmol) N-(1,1-dimethylethyl)-1-methyl-2-(methylthio)-1H-pyrrole-3-sulfonamide in 50 mL of methylene chloride was added 50 mL of trifiuoroacetic acid (TFA) under a nitrogen atmosphere. The orange reaction mixture was stirred at room temperature overnight ca. 16 hours. The reaction mixture was concentrated to a tan solid. Diethyl ether was added to the tan solid and was removed by evaporation to remove residual TFA. The solid was suspended in diethyl ether and filtered giving 2.9 g of the title compound as a solid, m.p. 135.degree.-137.degree. C.
.sup.1 H NMR (Acetone-d.sub.6, 200 MHz.) .delta.: 6.93(d,1H), 6.45(d,1H), 6.19(bs,2H), 3.78(s,3H), 2.33(s,3H).
EXAMPLE 9
2-Bromo-N-(1,1-dimethylethyl)-1-methyl-1H-pyrrole-3-sulfonamide
To a solution of 8.85 g (41 mmol) of N-(1,1-dimethylethyl)-1-methyl-1H-pyrrole-3-sulfonamide in 200 ml, diethyl ether under a nitrogen atmosphere cooled to -78.degree. C. was added dropwise, at such a rate as to keep the temperature below -65.degree. C., 36.0 mL (85 mmol) 2.41M n-butyllithium in hexanes. The reaction was stirred at -78.degree. C. for ca. 15 minutes. To the reaction mixture was added 2.2 ml, (41 mmol) of bromine dropwise. The light orange reaction mixture was allowed to warm to room temperature and stir for ca. 2 hours. The reaction mixture darkened as it stirred at room temperature. The reaction mixture was cooled to 0.degree. C. and acidified with 1N HCl. The ether phase was separated, washed with brine, dried (MgSO.sub.4) and concentrated in vacuo. The crude residue was chromatographed on silica (25% ethyl acetate/80% hexanes) affording 7.11 g of the title compound as an orange oil.
.sup.1 H NMR (CDCl.sub.3, 200 MHz.) .delta.: 6.73(d,1H), 6.62(d,1H), 3.63(s,3H), 1.24(s,9H).
EXAMPLE 10
2-Bromo-1-methyl-1H-pyrrole-3-sulfonamide
To a solution of 7.11 g (24 mmol) of 2-bromo-N-(1,1-dimethylethyl)-1-methyl-1H-pyrrole-3-sulfonamide in 50 mL methylene chloride under a nitrogen atmosphere was added 50 mL of TFA. The reaction mixture was allowed to stir at room temperature overnight ca. 16 hours. The reaction mixture was concentrated in vacuo. Three portions of diethyl ether were added to the crude residue and was removed by evaporation to remove residual TFA, which yielded 1.23 g of the title compound as a light brown solid.
.sup.1 H NMR (Acetone-d.sub.6, 200 MHz.) .delta.: 7.36(d,1H), 6.49(d,1H), 6.3(bs,2H) 3.68(s,3H).
EXAMPLE 11
N-(1,1-Dimethylethyl)-2-formyl-1-methyl-1H-pyrrole-3-sulfonamide
To a solution of 12.96 g (60 mmol) of N-(1,1-dimethylethyl)-1-methyl-1H-pyrrole-3-sulfonamide in 300 mL THF under a nitrogen atmosphere cooled to -78.degree. C. was added dropwise, at such a rate as to keep the temperature below -65.degree. C., 52.35 ml, (123 mmol) 2.35M n-butyllithium in hexanes. The reaction was stirred at -78.degree. C. for ca. 30 minutes. To the reaction mixture was added 4.64 ml, (60 mmol) of N,N-dimethylformamide dropwise. The reaction mixture was allowed to warm to room temperature and stir for ca. 2 hours. The reaction mixture was cooled to 0.degree. C. and acidified with 1N HCl. The THF phase was separated, washed with brine, dried (MgSO.sub.4) and concentrated in vacuo. The crude residue was chromatographed on silica (25% ethyl acetate/80% hexanes) affording 5.72 g of the title compound as a white solid, m.p. 101.5.degree.-103.degree. C.
.sup.1 H NMR (CDCl.sub.3, 200 MHz.) .delta.: 10.25(s,1H), 6.81(d,1H), 6.6(d,1H), 4.93(bs,1H), 3.98(s,3H), 1.27(s.9H).
EXAMPLE 12
N-(1,1-Dimethylethyl)-2-[(methoxyimino)-methyl]-1H-pyrrole-3-sulfonamide
To a suspension of 3.91 g (46.8 mmol) of methoxyamine hydrochloride in 60 mL of methanol was added 3.84 g (46.8 mmol) of sodium acetate. After stirring the white suspension for ca. 15 minutes 5.72 g (23 mmol) of N-(1,1-dimethylethyl)-2-formyl-1-methyl-1H-pyrrole-3-sulfonamide was added in one portion. The white suspension was heated at a gentle reflux overnight ca. 16 hours. The reaction mixture was cooled to room temperature and poured into 500 mL of water. The aqueous mixture was extracted with four 100 mL, portions of methylene chloride. The combined extracts were washed with water, dried (MgSO.sub.4) and concentrated in vacuo yielding 5.74 g of the title compound as a white solid, m.p. 99.degree.-101.degree. C.
.sup.1 H NMR (CDCl.sub.3, 200 MHz.) .delta.: 8.51(s,1H), 6.66(d,1H), 6.54(d,1H), 4.82(bs,1H), 3.97(s,3H), 3.82(s,3H), 1.24(s,9H).
EXAMPLE 13
2-[(Methoxyimino)methyl]-1-methyl-1H-pyrrole-3-sulfonamide
To a solution of 5.74 g (21.9 mmol) of N-(1,1-dimethylethyl)-2-[(methoxyimino)-methyl]-1H-pyrrole-3-sulfonamide in 75 mL methylene chloride under a nitrogen atmosphere was add 75 mL, of TFA. The clear orange reaction mixture was allowed to stir at room temperature overnight ca. 16 hours. The orange reaction mixture was concentrated in vacuo. Three portions of diethyl ether were added to the residue and removed by evaporation to remove residual TFA, affording 3.49 g of the title compound as a gray solid, m.p. 120.degree.-122.degree. C.
.sup.1 H NMR (CDCl.sub.3, 200 MHz.) .delta.: 8.43(s,1H), 6.66(d,1H), 6.54(d,1H), 6.1-6.7(bs,2H), 3.96(s,3H), 3.79(s,3H).
EXAMPLE 14
N.sup.3 -(1,1-Dimethylethyl)-N.sup.2,N.sup.2,1-trimethyl -1H-pyrrole-2,3-disulfonamide
A solution of 6.48 g (30 mmol) of N-(1,1-dimethylethyl)-1-methyl-1H-pyrrole-3-sulfonamide in 150 mL of anhydrous tetrahydrofuran (THF) under nitrogen atmosphere was cooled to -78.degree. C. The colorless reaction was treated with 61.5 mmol of 2.38M n-butyllithium in hexanes dropwise at such a rate as to keep the temperature below -65.degree. C. After ca. 1 hour at -78.degree. C., liquified sulfur dioxide was added (180 mmol). The amber solution was warmed to room temperature and stirred for ca. 1 hour. The THF was removed under reduced pressure. The residue was dissolved in 150 mL glacial acetic acid, cooled to 20.degree. C. and then treated with 31 mmol of N-chlorosuccinimide. After ca. 1 hour at room temperature the acetic acid was evaporated at reduced pressure and the residue was dissolved in ethyl acetate. This solution was washed successively with water, NaHCO.sub.3 solution, brine, dried (MgSO.sub.4) and evaporated in vacuo. The residue was dissolved in methylene chloride (150 mL), cooled to -20.degree. C. and treated with 75 mmol of liquified dimethylomine. The reaction mixture was allowed to warm to room temperature and stir overnight ca. 16 hours. The solution was washed with 1N HCl, dried (MgSO.sub.4) and evaporated. The crude material was dissolved in acetonitrile and treated with activated charcoal, filtered and concentrated. The residue was triturated with hexanes/n-butyl chloride to yield 6.95 g of the title compound as a light brown solid, m.p. 98.degree.-101.degree. C.
.sup.1 H NMR (CDCl.sub.3, 200 MHz.) .delta.: 6.79(d,1H), 6.69(d,1H), 5.77(bs,1H), 3.89(s,3H), 2.92(s,6H), 1.23(s,9H).
EXAMPLE 15
N.sup.2,N.sup.2 1-Trimethyl-1H-pyrrole-2,3-disulfonamide
To a solution of 6.95 g (21 mmol) of N.sup.3 -(1,1-dimethylethyl)-N.sup.2,N.sup.2 1-trimethyl-1H-pyrrole-2,3-disulfonamide in 75 mL of methylene chloride under a nitrogen atmosphere was added 75 mL of TFA. The reaction mixture was allowed to stir at room temperature overnight ca. 16 hours. The reaction mixture was concentrated in vacuo. Three portions of diethyl ether were added to the solid residue and removed by evaporation to remove residual TFA. The solids were suspended in diethyl ether and filtered to yield 4.52 g of the title compound as a solid, m.p. 146.degree.-148.degree. C.
.sup.1 H NMR (Acetone-d.sub.6, 200 MHz.) .delta.: 7.1(d,1H), 6.59(d,1H), 6.28(bs,2H), 3.95(s,3H), 2.93(s,6H).
EXAMPLE 16
N-[[(4-Ethyl-6-methoxy-1,3,5-triazinyl-2-yl)amino]-carbonyl-N,N,1-trimethyl-2,3-disulfonamide
0.27 g (1 mmol) of N.sup.2,N.sup.2,1-trimethyl-1H-pyrrole-2,3-disulfonamide and 0.28 g (1 mmol) of phenyl (4-ethyl-6-methoxy-2-triazinyl) carbamate were combined in 4 mL of acetonitrile 0.2 mL (1.33 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene was added and the resulting amber reaction mixture was allowed to stand at room temperature overnight ca. 16 hours. The reaction mixture was diluted with 6 ml, of water and ca. 2 mL of shaved ice, and was acidified with conc. HCl. The resulting precipitate was filtered, washed with water followed by diethyl ether, and air dried affording 0.19 g of the title compound as a solid, m.p. 159.degree.160.5.degree. C.
.sup.1 H NMR (Me.sub.2 SO-d.sub.6, 200 MHz.) .delta.: 12.52(bs,1H), 11.0(s,1H), 7.27(d,1H), 6.75(d,1H), 3.97(s,3H), 3.85(s,3H), 2.80(s,6H), 2.73(q,2H), 1.25(t,3H).
EXAMPLE 17
3-[[(1,1-Dimethylethyl)amino]sulfonyl]-N,N,1-trimethyl-1H-pyrrole-2-carboxamide
To a solution of 6.48 g (30 mmol) of N-(1,1-dimethylethyl)-1-methyl-1H-pyrrole-3-sulfonamide in 150 mL, THF under a nitrogen atmosphere cooled to -78.degree. C. was added dropwise, at such a rate as to keep the temperature below -60.degree. C., 25 mL (61.5 mmol) 2.46M n-butyllithium in hexanes. The reaction mixture was stirred at -78.degree. C. for ca. 30 minutes. To the reaction mixture was added dropwise a solution of 3.1 mL (33 mmol) of N,N-dimethylcarbamyl chloride in 10 mL of THF at such a rate as to maintain the temperature below -65.degree. C. The reaction mixture was allowed to warm to room temperature and stir for ca. 1.5 hours. The reaction mixture was cooled to ca. 5.degree. C. and 60 mL of 50% ammonium chloride solution was added. The reaction mixture was stirred for ca. 15 minutes. The pH was adjusted to ca. 3 with 1N HCl (ca. 30 mL), and the aqueous phase was separated from the THF phase and extracted with ethyl acetate. The combined THF and ethyl acetate extracts were washed with brine, dried (MgSO.sub.4) and concentrated in vacuo to an oil. The oil was chromatographed on silica with (20% ethyl acetate/80% n-butyl chloride) affording 4.33 g of the title compound as a pale yellow solid.
.sup.1 H NMR(CDCl.sub.3, 200 MHz.) .delta.: 6.61(d,1H), 6.46(d,1H), 4.62(bs,1H), 3.59(s,3H), 3.1(s,3H), 2.95(s,3H), 1.24(s,9H).
EXAMPLE 18
3-(Aminosulfonyl)-N,N,1-trimethyl-1H-pyrrole-2-carboxamide
To a solution of 5.63 g of 3-[[(1,1-dimethylethyl)amino]sulfonyl]-N,N,1-trimethyl-1H-pyrrole-2-carboxamide in 75 ml, of methylene chloride was added 75 mL of TFA. The reaction mixture was allowed to stir at room temperature overnight ca. 16 hours. The reaction mixture was concentrated in vacuo. Three portions of diethyl ether were added to the residue and removed by evaporation to remove residual TFA, affording 4.21 g of the title compound as a gray solid, m.p. 185.degree.-190.5.degree. C.
.sup.1 H NMR(Me.sub.2 SO-d.sub.6, 200 MHz.) .delta.: 6.99(bs,2H), 6.88(d,1H), 6.34(d,1H), 3.47(s,3H), 2.96(s,3H), 2.81(s,3H).
EXAMPLE 19
N-(1,1-Dimethylethyl)-1-methyl-1H pyrrole-2-sulfonamide
A solution of 10 g (0.12 mol) of N-methyl-pyrrole in 120 ml, of anhydrous THF under nitrogen atmosphere was cooled to below -70.degree. C. then treated with 56 ml, of 2.4M n-butyllithium in hexanes (0.13 mol) dropwise at such a rate as to keep the temperature below -60.degree. C. The resulting brown colored mixture was stirred for 16 h at ambient temperature, then recooled to below -70.degree. C. at which time liquified sulfur dioxide (9.0 mL, 0.21 mol) was added rapidly, causing an exotherm at -20.degree. C. and the formation of a thick golden colored precipitate. After stirring for 1 h at ambient temperature, the THF was removed under reduced pressure. The solids were triturated with ether and collected by filtration with an ether rinse then dried under nitrogen. This intermediate sulfinate salt was added to a well stirred mixture of 350 water and 250 mL dichloromethane chilled to 0.degree. C. N-Chlorosuccinimide was then added in portions so as to keep the temperature below 3.degree. C. The mixture was stirred vigorously for 30 min at ambient temperature, after which time, the layers were separated and the organic layer was washed successively with 10% aq NaHSO.sub.3, twice with aq NaHCO.sub.3, dried (MgSO.sub.4) and filtered. This dichloromethane solution was then cooled to 0.degree. C. and stirred while 32 ml, (0.30 mol) of t-butylamine was added over 2 min. After stirring for 1 h at ambient temperature, solids had precipitated from the brown solution which was then left stirring for 3 days. The mixture was diluted with more dichloromethane then washed three times with 1N HCl, once with saturated aq NaCl, dried (MgSO.sub.4) and evaporated. The resulting solid residue was triturated and collected with a mixture of hexanes and n-chlorobutane to afford 7.4 g of the title compound as tan crystals, m.p. 125.degree.-126.degree. C.
.sup.1 H NMR (CDCl.sub.3, 200 MHz.) .delta.: 6.82(m, 1H), 6.78(m, 1H), 6.10(m, 1H), 4.53(bs,1H), 3.83(s,3H), 1.23(s,9H).
EXAMPLE 20
Methyl 2-[[(1,1-Dimethylethyl)amino]sulfonyl]-1-methyl-1H-pyrrole-3-carboxylate
To a solution of 2.5 g (11.5 mmol) of N-(1,1-dimethylethyl)-1-methyl- 1H-pyrrole-2-sulfonamide in 50 mL THF under nitrogen atmosphere cooled to below -70.degree. C. was added dropwise 13 ml, (32.5 mmol) of 2.5M n-butyllithium at such a rate as to keep the temperature below -58.degree. C. After stirring at -20.degree. C. to -10.degree. C. for 30 min then 1 h at 0.degree. C., the mixture was recooled to -70.degree. C. and treated with a solution of 1.63 g (17.3 mmol) of methyl chloroformate in 6 mL THF causing an exotherm to -57.degree. C. The reaction mixture was stirred overnight at ambient temperature then diluted with 200 mL of ethyl acetate. This solution was washed successively with two 60 ml, portions of 1N HCl, brine, then dried (Na.sub.2 SO.sub.4) and evaporated to a dark oil. The crude product was purified by chromatography on silica gel (30% ethyl acetate/70% hexanes) then collected from hexanes to afford 0.45 g of the title compound, m.p. 105.degree.-108.degree. C.
.sup.1 H NMR (CDCl.sub.3, 200 MHz.) .delta.: 7.00(bs,1H), 6.61(m,2H), 3.94(s,3H), 3.85(s,3H), 1.21(s,9H).
EXAMPLE 21
Methyl 2-(Aminosulfonyl)-1-methyl-1H-pyrrole-3-carboxylate
A solution of 0.45 g (1.64 mmol) of methyl 2-[[(1,1-dimethylethyl)amino]sulfonyl]-1-methyl-1H-pyrrole-3-carboxylate in 20 mL TFA was prepared and stirred at ambient temperature for 3 hours. The TFA was then removed under reduced pressure and chloroform added to the residue and evaporated again to remove residual TFA. The resulting solid was suspended in water, filtered, and dried under vacuum to afford 0.25 g of the title compound, m.p. 119.degree.-121.degree. C., (dec).
.sup.1 H NMR (Me.sub.2 SO-d.sub.6, 200 MHz.) .delta.: 7.40(bs,2H), 7.02(d,1H), 6.48(d,1H), 3.84(s,3H), 3.76(s,3H).
EXAMPLE 22
Methyl 2-[[[[(4,6-Dimethoxy-2-pyrmidinyl)amino]-carbonyl]amino]sulfonyl-1-methyl-1H-pyrrole-3-carboxylate
Methyl 2-(aminosulfonyl)-1-methyl-1H-pyrrole-3-carboxylate (0.10 g, 0.46 mmol) and 0.13 g (0.50 mmol) of phenyl (4,6-dimethoxy-2pyrimidinyl)carbamate were combined in 2 mL of acetonitrile and 0.075 mL of DBU was added and the resulting amber solution was stirred at ambient temperature for 30 min. The reaction mixture was diluted with 15 mL of water and acidified with 0.5 mL, 1N HCl and the resulting precipitate was collected by filtration and rinsed successively with water and ether, then dried to afford 0.15 g of the title compound as a white solid, m.p. 192.degree.-193.degree. C. (dec).
.sup.1 H NMR (Me.sub.2 SO-d.sub.6, 200 MHz.) .delta.: 12.7(NH), 10.7(NH), 7.22(d,1H), 6.60(d,1H), 6.02(s,1H), 3.98(s,3H), 3.96(s,6H), 3.68 (s,3H).
EXAMPLE 23
Methyl 2-[[[[(4-Methoxy-6-methyl-1,3,5-triazin -2-yl)amino]carbonyl]amino]sulfonyl]-1-methyl-1H-pyrrole-3-carboxylate
Methyl 2-(aminosulfonyl)-1-methyl-1H-pyrrole-3-carboxylate (0.10 g, 0.46 mmol) and 0.13 g (0.50 mmol) of phenyl (4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamate were combined in 2 mL of acetonitrile and 0.075 mL of DBU was added and the resulting amber solution was stirred at ambient temperature for 30 min. The reaction mixture was diluted with 15 mL of water and acidified with 0.5 mL 1N HCl and the resulting precipitate was collected by filtration and rinsed successively with water and ether, then dried to afford 0.13 g of the title compound as a white solid, m.p. 189.degree.-190.degree. C. (dec).
.sup.1 H NMR (Me.sub.2 SO-d.sub.6, 200 MHz.) .delta.: 12.5(NH), 11.1(NH), 7.22(d,1H), 6.60(d,1H), 4.01(s,3H), 3.98(s,3H), 3.71(s,3H), 2.49(s,3H).
By applying the procedures of Examples 1 through 23 and Equations 1 through 24, one skilled in the art can prepare the compounds in Tables 1 through 5. In the following tables, abbreviations for various alkyl chains and rings have been used with the following corresponding definitions.
______________________________________Et = ethyl = CH.sub.2 CH.sub.3,iPr = isopropyl = CH(CH.sub.3).sub.2,nPr = n-propyl = CH.sub.2 CH.sub.2 CH.sub.3,cPr = cyclopropyl = CH(CH.sub.2).sub.2,cBu = cyclobutyl = CH(CH.sub.2).sub.3,cC.sub.5 H.sub.9 = cyclopentyl = CH(CH.sub.2).sub.4.t-Bu = tert-butyl = C(CH.sub.3).sub.3n-Bu = n-butyl = (CH.sub.2).sub.3 CH.sub.3cC.sub.6 H.sub.11 = cyclohexyl = CH(CH.sub.2).sub.5______________________________________
TABLE 1__________________________________________________________________________ ##STR49##R = H, R.sup.1 = CH.sub.3, R.sup.2 = CO.sub.2 CH.sub.3, R.sup.4 = H,R.sup.71 = HX Y Z X Y Z__________________________________________________________________________CH.sub.3 CH.sub.3 CH NHCH.sub.3 OCH.sub.3 NCH.sub.3 OCH.sub.3 CH N(CH.sub.3).sub.2 OCH.sub.3 NOCH.sub.3 OCH.sub.3 CH C.sub.2 H.sub.5 OC.sub.2 H.sub.5 NCl OCH.sub.3 CH NHCH.sub.3 OC.sub.2 H.sub.5 NCH.sub.3 OC.sub.2 H.sub.5 CH N(CH.sub.3).sub.2 OC.sub.2 H.sub.5 NC.sub.2 H.sub.5 OCH.sub.3 CH NHCH.sub.3 OCH.sub.2 CF.sub.3 NH OCH.sub.3 CH N(CH.sub.3).sub.2 OCH.sub.2 CF.sub.3 NH OC.sub.2 H.sub.5 CH CH.sub.3 OC.sub.2 H.sub.5 NOCH.sub.3 CH.sub.2 OCH.sub.3 CH CF.sub.3 OCH.sub.3 NCH.sub.3 CH(OCH.sub.3).sub.2 CH OCF.sub.2 H OCH.sub.3 NOCHF.sub.3 OCH.sub.3 CH CH.sub.3 OCH.sub.2 CHCH.sub.2 NOCH.sub.3 SCH.sub.3 CHCH.sub.3 OCH.sub.3 NOCH.sub.3 OCH.sub.3 N__________________________________________________________________________Z = CHX Y X Y__________________________________________________________________________(CH.sub.2).sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CH.sub.2 SO.sub.2 CH.sub.3iPr OCH.sub.3 OCH.sub.3 cBu(CH.sub.2).sub.4 Cl OCH.sub.3 CH.sub.3 O(CH.sub.2).sub.2 CHCH.sub.2SEt SEt SCH.sub.2 CF.sub.3 OCH.sub.3S(CH.sub.2).sub.3 CH.sub.3 OCH.sub.3 SCHF.sub.2 CH.sub.3OCH.sub.2 OEt CH.sub.3 CF.sub.3 CF.sub.3O(CH.sub.2).sub.2 OiPr OCH.sub.3 CH.sub.2 Cl OCH.sub.3O(CH.sub.2).sub.2 OCH.sub.3 OC.sub.2 H.sub.5 CH.sub.2 Br OCH.sub.3CH.sub.2 CH.sub.2 OCH.sub.3 Et CH.sub.2 F OEtH H I OCH.sub.3Cl N(CH.sub.3).sub.2 OCH.sub.2 CHF.sub.2 CH.sub.3Br NHCH.sub.3 NHiPr CH.sub.3OCH.sub.3 CN N(iPr).sub.2 CH.sub.3CH.sub.3 CH.sub.2 CCH OCH.sub.2 CF.sub.3 OCH.sub.2 CF.sub.3CH OCH.sub.2 CCH NEt.sub.2 NEt.sub.2OCH.sub.3 OCH.sub.2 CHCH.sub.2 OCH.sub.3 N.sub.3NEt.sub.2 OCH.sub.3 CH.sub.3 cPrOCH.sub.2 iPr OCH.sub.3 CH.sub.3 CH.sub.2 SEtNH.sub.2 CH.sub.3 OCH.sub.3 cC.sub.5 H.sub.9N(CH.sub.3)Et OCH.sub.3 O(CH.sub.2).sub.3 Cl O(CH.sub.2).sub.3 ClCl OC.sub.2 H.sub.5Br OCH.sub.3OCF.sub.2 H OCF.sub.2 HOCH.sub.2 CF.sub.3 OCF.sub.2 HOCH.sub.2 CF.sub.3 CH.sub.3OCH.sub.2 CH.sub.2 CH.sub.2 F OCH.sub.3OiPr OCH.sub.3CH.sub.3 N(OCH.sub.3)CH.sub.3O(CH.sub.2).sub.3 CH.sub.3 O(CH.sub.2).sub.3 CH.sub.3iPr iPrOCH.sub.3 cPr__________________________________________________________________________Z = NX Y__________________________________________________________________________N(CH.sub.3).sub.2 N(CH.sub.3).sub.2OEt NHnBuOCH.sub.3 NHiPrOCH.sub.2 F NHtBuOCH.sub.3 OCF.sub.2 BrNEt.sub.2 NEt.sub.2OCH.sub.3 NEt.sub.2OEt NHCH.sub.2 CF.sub.3OCH.sub.3 N(CH.sub.2 CF.sub.3).sub.2OCH.sub.3 StBuOCH.sub.3 CNOCH.sub.3 N.sub.3OEt cPrOCH.sub.3 OCH.sub.2 CHCH.sub.2CH.sub.3 CH.sub.3__________________________________________________________________________ ##STR50##X R.sup.22 Z__________________________________________________________________________CH.sub.3 CH.sub.3 CHOCH.sub.3 CH.sub.3 CHCH.sub.3 H CHOCH.sub.3 H CHCH.sub.3 (CH.sub.2).sub.2 CH.sub.3 CHCH.sub.3 CH.sub.3 NOCH.sub.3 CH.sub.3 NCH.sub.3 H NOEt H CHOCH.sub.3 Et N__________________________________________________________________________ ##STR51##X R.sup.22 Q.sup.3 R.sup.23 Q.sup.4 R.sup.24 Z__________________________________________________________________________OCH.sub.3 CH3 OCH.sub.3 OCH.sub.3 CHCH.sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CHOCH.sub.3 Et OCH.sub.3 OCH3 NOCH.sub.3 CH.sub.3 SEt SEt CHCH.sub.3 CH.sub.3 S-nPr SCH.sub.3 CHOCH.sub.3 nPr OCH.sub.3 OiPr CH__________________________________________________________________________ ##STR52##X R.sup.22 Q.sup.3 Q.sup.4 p Z__________________________________________________________________________OCH.sub.3 CH.sub.3 S S 2 CHCH.sub.3 CH.sub.3 O O 2 CHCH.sub.3 CH.sub.3 O O 3 CHOCH.sub.3 CH.sub.3 S O 2 NOEt CH.sub.3 O O 2 CHOCH.sub.3 Et S O 3 N__________________________________________________________________________Z = CH ##STR53##X R.sup.22 Q.sup.3 Q.sup.4__________________________________________________________________________OCH.sub.3 CH.sub.3 O OCH.sub.3 Et O OOCH.sub.3 nPr O OCH.sub.3 CH.sub.3 S SOCH.sub.3 Et O OOCH.sub.3 CH.sub.3 S O__________________________________________________________________________R.sup.2 = CO.sub.2 CH.sub.3, R.sup.71 = H, R = H, R.sup.1 = CH.sub.3, R.sup.71 = H,R = R.sup.4 = H, R.sup.1 = CH.sub.2 OCH.sub.3 R.sup.2 = CO.sub.2 C.sub.2 H.sub.5, R.sup.4 = HX Y Z X Y Z__________________________________________________________________________CH.sub.3 CH.sub.3 CH CH.sub.3 CH.sub.3 CHCH.sub.3 OCH.sub.3 CH CH.sub.3 OCH.sub.3 CHOCH.sub.3 OCH.sub.3 CH OCH.sub.3 OCH.sub.3 CHCl OCH.sub.3 CH Cl OCH.sub.3 CHCH.sub.3 OC.sub.2 H.sub.5 CH CH.sub.3 OC.sub.2 H.sub.5 CHC.sub.2 H.sub.5 OCH.sub.3 CH C.sub.2 H.sub.5 OCH.sub.3 CHH OCH.sub.3 CH H OCH.sub.3 CHH OC.sub.2 H.sub.5 CH H OC.sub.2 H.sub.5 CHOCH.sub.3 CH.sub.2 OCH.sub.3 CH OCH.sub.3 CH.sub.2 OCH.sub.3 CHCH.sub.3 CH(OCH.sub.3).sub.2 CH CH.sub.3 CH(OCH.sub.3).sub.2 CHOCHF.sub.2 OCH.sub.3 CH OCHF.sub.2 OCH.sub.3 CHOCH.sub.3 SCH.sub.3 CH OCH.sub.3 SCH.sub.3 CHCH.sub.3 OCH.sub.3 N CH.sub.3 OCH.sub.3 NOCH.sub.3 OCH.sub.3 N OCH.sub.3 OCH.sub.3 NNHCH.sub.3 OCH.sub.3 N NHCH.sub.3 OCH.sub.3 NN(CH.sub.3).sub.2 OCH.sub.3 N N(CH.sub.3).sub.2 OCH.sub.3 NC.sub.2 H.sub.5 OC.sub.2 H.sub.5 N C.sub.2 H.sub.5 OC.sub.2 H.sub.5 NNHCH.sub.3 OC.sub.2 H.sub.5 N NHCH.sub.3 OC.sub.2 H.sub.5 NN(CH.sub.3).sub.2 OC.sub.2 H.sub.5 N N(CH.sub.3).sub.2 OC.sub.2 H.sub.5 NNHCH.sub.3 OCH.sub.2 CF.sub.3 N NHCH.sub.3 OCH.sub.2 CF.sub.3 NN(CH.sub.3).sub.2 OCH.sub.2 CF.sub.3 N N(CH.sub.3).sub.2 OCH.sub.2 CF.sub.3 NCH.sub.3 OC.sub.2 H.sub.5 N CH.sub.3 OC.sub.2 H.sub.5 NCF.sub.3 OCH.sub.3 N CF.sub.3 OCH.sub.3 NOCF.sub.2 H OCH.sub.3 N OCF.sub.2 H OCH.sub.3 NCH.sub.3 OCH.sub.2 CHCH.sub.2 N CH.sub.3 OCH.sub.2 CHCH.sub.2 N__________________________________________________________________________R = R.sup.4 = H, R.sup.71 = H, R = H, R.sup.4 = H, R.sup.1 = CH.sub.3,R.sup.2 = SO.sub.2 CH.sub.3, R.sup.1 = CH.sub.3 R.sup.71 = H, R.sup.2 = SO.sub.2 N(CH.sub.3).sub.2X Y Z X Y Z__________________________________________________________________________CH.sub.3 CH.sub.3 CH CH.sub.3 CH.sub.3 CHCH.sub.3 OCH.sub.3 CH CH.sub.3 OCH.sub.3 CHOCH.sub.3 OCH.sub.3 CH OCH.sub.3 OCH.sub.3 CHCl OCH.sub.3 CH Cl OCH.sub.3 CHCH.sub.3 OC.sub.2 H.sub.5 CH CH.sub.3 OC.sub.2 H.sub.5 CHC.sub.2 H.sub.5 OCH.sub.3 CH C.sub.2 H.sub.5 OCH.sub.3 CHH OCH.sub.3 CH H OCH.sub.3 CHH OC.sub.2 H.sub.5 CH H OC.sub.2 H.sub.5 CHOCH.sub.3 CH.sub.2 OCH.sub.3 CH OCH.sub.3 CH.sub.2 OCH.sub.3 CHCH.sub.3 CH(OCH.sub.3).sub.2 CH CH.sub.3 CH(OCH.sub.3).sub.2 CHOCHF.sub.2 OCH.sub.3 CH OCHF.sub.3 OCH.sub.3 CHOCH.sub.3 SCH.sub.3 CH OCH.sub.3 SCH.sub.3 CHCH.sub.3 OCH.sub.3 N CH.sub.3 OCH.sub.3 NOCH.sub.3 OCH.sub.3 N OCH.sub.3 OCH.sub.3 NNHCH.sub.3 OCH.sub.3 N NHCH.sub.3 OCH.sub.3 NN(CH.sub.3).sub.2 OCH.sub.3 N N(CH.sub.3).sub.2 OCH.sub.3 NC.sub.2 H.sub.5 OC.sub.2 H.sub.5 N C.sub.2 H.sub.5 OC.sub.2 H.sub.5 NNHCH.sub.3 OC.sub.2 H.sub.5 N NHCH.sub.3 OC.sub.2 H.sub.5 NN(CH.sub.3).sub.2 OC.sub.2 H.sub.5 N N(CH.sub.3).sub.2 OC.sub.2 H.sub.5 NNHCH.sub.3 OCH.sub.2 CF.sub.3 N NHCH.sub.3 OCH.sub.2 CF.sub.3 NN(CH.sub.3).sub.2 OCH.sub.2 CF.sub.3 N N(CH.sub.3).sub.2 OCH.sub.2 CF.sub.3 NCH.sub.3 OC.sub.2 H.sub.5 N CH.sub.3 OC.sub.2 H.sub.5 NCF.sub.3 OCH.sub.3 N CF.sub.3 OCH.sub.3 NOCF.sub.2 H OCH.sub.3 N OCF.sub.2 H OCH.sub.3 NCH.sub.3 OCH.sub.2 CHCH.sub.2 N CH.sub.3 OCH.sub.2 CHCH.sub.2 N__________________________________________________________________________R.sup.1 = C.sub.2 H.sub.5, R.sup.71 = H, R.sup.1 = CH.sub.3, R.sup.4 = H, R.sup.71 = H,R.sup.2 = CO.sub.2 CH.sub.3, R.sup.4 = Br R.sup.2 = 2-pyridylR X Y Z R X Y Z__________________________________________________________________________H CH.sub.3 CH.sub.3 CH H CH.sub.3 CH.sub.3 CHH CH.sub.3 OCH.sub.3 CH H CH.sub.3 OCH.sub.3 CHH OCH.sub.3 OCH.sub.3 CH H OCH.sub.3 OCH.sub.3 CHH Cl OCH.sub.3 CH H Cl OCH.sub.3 CHCH.sub.3 OCH.sub.3 OCH.sub.3 CH CH.sub.3 OCH.sub.3 OCH.sub.3 CHH CH.sub.3 OCH.sub.3 N H CH.sub.3 OCH.sub.3 NH OCH.sub.3 OCH.sub.3 N H OCH.sub.3 OCH.sub.3 NH NHCH.sub.3 OC.sub.2 H.sub.5 N N NHCH.sub.3 OC.sub.2 H.sub.5 NH N(CH.sub.3).sub.2 OC.sub.2 H.sub.5 N H N(CH.sub.3).sub.2 OC.sub.2 H.sub.5 NCH.sub.3 OCH.sub.3 OCH.sub.3 N CH.sub.3 OCH.sub.3 OCH.sub.3 N__________________________________________________________________________R.sup.1 = C.sub.2 H.sub.5, R.sup.71 = H, R.sup.1 = CH.sub.3, R.sup.4 = H,R.sup.2 = 2-thienyl, R.sup.4 = H R.sup.71 = H, R.sup.2 = S(O)C.sub.2 H.sub.5R X Y Z R X Y Z__________________________________________________________________________H CH.sub.3 CH.sub.3 CH H CH.sub.3 CH.sub.3 CHH CH.sub.3 OCH.sub.3 CH H CH.sub.3 OCH.sub.3 CHH OCH.sub.3 OCH.sub.3 CH H OCH.sub.3 OCH.sub.3 CHH Cl OCH.sub.3 CH H Cl OCH.sub.3 CHCH.sub.3 OCH.sub.3 OCH.sub.3 CH CH.sub.3 OCH.sub.3 OCH.sub.3 CHH CH.sub.3 OCH.sub.3 N H CH.sub.3 OCH.sub.3 NH OCH.sub.3 OCH.sub.3 N H OCH.sub.3 OCH.sub.3 NH NHCH.sub.3 OC.sub.2 H.sub.5 N N NHCH.sub.3 OC.sub.2 H.sub.5 NH N(CH.sub.3).sub.2 OC.sub.2 H.sub.5 N H N(CH.sub.3).sub.2 OC.sub.2 H.sub.5 NCH.sub.3 OCH.sub.3 OCH.sub.3 N CH.sub.3 OCH.sub.3 OCH.sub.3 N__________________________________________________________________________R = H, R.sup.1 = CH.sub.3, R.sup.4 = H, R = H, R.sup.1 = CH.sub.3, R.sup.4 = H,R.sup.71 = H, R.sup.2 = C(O)CH.sub.3 R.sup.71 = H, R.sup.2 =C(H)NOCH.sub.3X Y Z X Y Z__________________________________________________________________________CH.sub.3 CH.sub.3 CH CH.sub.3 CH.sub.3 CHCH.sub.3 OCH.sub.3 CH CH.sub.3 OCH.sub.3 CHOCH.sub.3 OCH.sub.3 CH OCH.sub.3 OCH.sub.3 CHCl OCH.sub.3 CH Cl OCH.sub.3 CHCH.sub.3 OC.sub.2 H.sub.5 CH CH.sub.3 OC.sub.2 H.sub.5 CHC.sub.2 H.sub.5 OCH.sub.3 CH C.sub.2 H.sub.5 OCH.sub.3 CHH OCH.sub.3 CH H OCH.sub.3 CHH OC.sub.2 H.sub.5 CH H OC.sub.2 H.sub.5 CHOCH.sub.3 CH.sub.2 OCH.sub.3 CH OCH.sub.3 CH.sub.2 OCH.sub.3 CHCH.sub.3 CH(OCH.sub.3).sub.2 CH CH.sub.3 CH(OCH.sub.3).sub.2 CHOCHF.sub.2 OCH.sub.3 CH OCHF.sub.2 OCH.sub.3 CHOCH.sub.3 SCH.sub.3 CH OCH.sub.3 SCH.sub.3 CHCH.sub.3 OCH.sub.3 N CH.sub.3 OCH.sub.3 NOCH.sub.3 OCH.sub.3 N OCH.sub.3 OCH.sub.3 NNHCH.sub.3 OCH.sub.3 N NHCH.sub.3 OCH.sub.3 NN(CH.sub.3).sub.2 OCH.sub.3 N N(CH.sub.3).sub.2 OCH.sub.3 NC.sub.2 H.sub.5 OC.sub.2 H.sub.5 N C.sub.2 H.sub.5 OC.sub.2 H.sub.5 NNHCH.sub.3 OC.sub.2 H.sub.5 N NHCH.sub.3 OC.sub.2 H.sub.5 NN(CH.sub.3).sub.2 OC.sub.2 H.sub.5 N N(CH.sub.3).sub.2 OC.sub.2 H.sub.5 NNHCH.sub.3 OCH.sub.2 CF.sub.3 N NHCH.sub.3 OCH.sub.2 CF.sub.3 NN(CH.sub.3).sub.2 OCH.sub.2 CF.sub.3 N N(CH.sub.3).sub.2 OCH.sub.2 CF.sub.3 NCH.sub.3 OC.sub.2 H.sub.5 N CH.sub.3 OC.sub.2 H.sub.5 NCF.sub.3 OCH.sub.3 N CF.sub.3 OCH.sub.3 NOCF.sub.2 H OCH.sub.3 N OCF.sub.2 H OCH.sub.3 NCH.sub.3 OCH.sub.2 CHCH.sub.2 N CH.sub.3 OCH.sub.2 CHCH.sub.2 N__________________________________________________________________________R.sup.4 = H, R.sup.71 = H, R.sup.1 = C.sub.2 H.sub.5, R.sup.1 = CH.sub.3, R.sup.4 = H, R.sup.71 = H,R.sup.2 = NO.sub.2 R.sup.2 = CH.sub.2 OCH.sub.3R X Y Z R X Y Z__________________________________________________________________________H CH.sub.3 CH.sub.3 CH H CH.sub.3 CH.sub.3 CHH CH.sub.3 OCH.sub.3 CH H CH.sub.3 OCH.sub.3 CHH OCH.sub.3 OCH.sub.3 CH H OCH.sub.3 OCH.sub.3 CHH Cl OCH.sub.3 CH H Cl OCH.sub.3 CHCH.sub.3 OCH.sub.3 OCH.sub.3 CH CH.sub.3 OCH.sub.3 OCH.sub.3 CHH CH.sub.3 OCH.sub.3 N H CH.sub.3 OCH.sub.3 NH OCH.sub.3 OCH.sub.3 N H OCH.sub.3 OCH.sub.3 NH NHCH.sub.3 OC.sub.2 H.sub.5 N N NHCH.sub.3 OC.sub.2 H.sub.5 NH N(CH.sub.3).sub.2 OC.sub.2 H.sub.5 N H N(CH.sub.3).sub.2 OC.sub.2 H.sub.5 NCH.sub.3 OCH.sub.3 OCH.sub.3 N CH.sub.3 OCH.sub.3 OCH.sub.3 N__________________________________________________________________________R.sup.1 = CH.sub.3, R.sup.71 = H, R.sup.1 = CH.sub.3, R.sup.4 = H, R.sup.71 = H,R.sup.2 = CH.sub.2 OC(O)CH.sub.3, R.sup.4 = H R.sup.2 = CH.sub.2 SCH.sub.3R X Y Z R X Y Z__________________________________________________________________________H CH.sub.3 CH.sub.3 CH H CH.sub.3 CH.sub.3 CHH CH.sub.3 OCH.sub.3 CH H CH.sub.3 OCH.sub.3 CHH OCH.sub.3 OCH.sub.3 CH H OCH.sub.3 OCH.sub.3 CHH Cl OCH.sub.3 CH H Cl OCH.sub.3 CHCH.sub.3 OCH.sub.3 OCH.sub.3 CH CH.sub.3 OCH.sub.3 OCH.sub.3 CHH CH.sub.3 OCH.sub.3 N H CH.sub.3 OCH.sub.3 NH OCH.sub.3 OCH.sub.3 N H OCH.sub.3 OCH.sub.3 NH NHCH.sub.3 OC.sub.2 H.sub.5 N N NHCH.sub.3 OC.sub.2 H.sub.5 NH N(CH.sub.3).sub.2 OC.sub.2 H.sub.5 N H N(CH.sub.3).sub.2 OC.sub.2 H.sub.5 NCH.sub.3 OCH.sub.3 OCH.sub.3 N CH.sub.3 OCH.sub.3 OCH.sub.3 N__________________________________________________________________________R.sup.1 = CH.sub.3, R.sup.71 = H, R.sup.1 = C.sub.2 H.sub.5, R.sup.4 = H, R.sup.71 = H,R.sup.2 = CH.sub.2 SO.sub.2 CH.sub.3, R.sup.4 = H R.sup.2 = CH.sub.2 OHR X Y Z R X Y Z__________________________________________________________________________H CH.sub.3 CH.sub.3 CH H CH.sub.3 CH.sub.3 CHH CH.sub.3 OCH.sub.3 CH H CH.sub.3 OCH.sub.3 CHH OCH.sub.3 OCH.sub.3 CH H OCH.sub.3 OCH.sub.3 CHH Cl OCH.sub.3 CH H Cl OCH.sub.3 CHCH.sub.3 OCH.sub.3 OCH.sub.3 CH CH.sub.3 OCH.sub.3 OCH.sub.3 CHH CH.sub.3 OCH.sub.3 N H CH.sub.3 OCH.sub.3 NH OCH.sub.3 OCH.sub.3 N H OCH.sub.3 OCH.sub.3 NH NHCH.sub.3 OC.sub.2 H.sub.5 N N NHCH.sub.3 OC.sub.2 H.sub.5 NH N(CH.sub.3).sub.2 OC.sub.2 H.sub.5 N H N(CH.sub.3).sub.2 OC.sub.2 H.sub.5 NCH.sub.3 OCH.sub.3 OCH.sub.3 N CH.sub.3 OCH.sub.3 OCH.sub.3 N__________________________________________________________________________R.sup.1 = CH.sub.3, R.sup.71 = H, R.sup.2 = CHF.sub.2, R.sup.1 = CH.sub.3, R.sup.4 = H,R.sup.4 = H R.sup.71 = H, R.sup.2 = CNR X Y Z R X Y Z__________________________________________________________________________H CH.sub.3 CH.sub.3 CH H CH.sub.3 CH.sub.3 CHH CH.sub.3 OCH.sub.3 CH H CH.sub.3 OCH.sub.3 CHH OCH.sub.3 OCH.sub.3 CH H OCH.sub.3 OCH.sub.3 CHH Cl OCH.sub.3 CH H Cl OCH.sub.3 CHCH.sub.3 OCH.sub.3 OCH.sub.3 CH CH.sub.3 OCH.sub.3 OCH.sub.3 CHH CH.sub.3 OCH.sub.3 N H CH.sub.3 OCH.sub.3 NH OCH.sub.3 OCH.sub.3 N H OCH.sub.3 OCH.sub.3 NH NHCH.sub.3 OC.sub.2 H.sub.5 N N NHCH.sub.3 OC.sub.2 H.sub.5 NH N(CH.sub.3).sub.2 OC.sub.2 H.sub.5 N H N(CH.sub.3).sub.2 OC.sub.2 H.sub.5 NCH.sub.3 OCH.sub.3 OCH.sub.3 N CH.sub.3 OCH.sub.3 OCH.sub.3 N__________________________________________________________________________ ##STR54## R.sup.71 = H, R.sup.2 = CHOR = H, R.sub.4 = H, R.sup.1 = CH.sub.3,X Y Z X Y Z__________________________________________________________________________CH.sub.3 CH.sub.3 CH CH.sub.3 CH.sub.3 CHCH.sub.3 OCH.sub.3 CH CH.sub.3 OCH.sub.3 CHOCH.sub.3 OCH.sub.3 CH OCH.sub.3 OCH.sub.3 CHCl OCH.sub.3 CH Cl OCH.sub.3 CHCH.sub.3 OC.sub.2 H.sub.5 CH CH.sub.3 OC.sub.2 H.sub.5 CHC.sub.2 H.sub.5 OCH.sub.3 CH C.sub.2 H.sub.5 OCH.sub.3 CHH OCH.sub.3 CH H OCH.sub.3 CHH OC.sub.2 H.sub.5 CH H OC.sub.2 H.sub.5 CHOCH.sub.3 CH.sub.2 OCH.sub.3 CH OCH.sub.3 CH.sub.2 OCH.sub.3 CHCH.sub.3 CH(OCH.sub.3).sub.2 CH CH.sub.3 CH(OCH.sub.3).sub.2 CHOCHF.sub.2 OCH.sub.3 CH OCHF.sub.2 OCH.sub.3 CHOCH.sub.3 SCH.sub.3 CH OCH.sub.3 SCH.sub.3 CHCH.sub.3 OCH.sub.3 N CH.sub.3 OCH.sub.3 NOCH.sub.3 OCH.sub.3 N OCH.sub.3 OCH.sub.3 NNHCH.sub.3 OCH.sub.3 N NHCH.sub.3 OCH.sub.3 NN(CH.sub.3).sub.2 OCH.sub.3 N N(CH.sub.3).sub.2 OCH.sub.3 NC.sub.2 H.sub.5 OC.sub.2 H.sub.5 N C.sub.2 H.sub.5 OC.sub.2 H.sub.5 NNHCH.sub.3 OC.sub.2 H.sub.5 N NHCH.sub.3 OC.sub.2 H.sub.5 NN(CH.sub.3).sub.2 OC.sub.2 H.sub.5 N N(CH.sub.3).sub.2 OC.sub.2 H.sub.5 NNHCH.sub.3 OCH.sub.2 CF.sub.3 N NHCH.sub.3 OCH.sub.2 CF.sub.3 NN(CH.sub.3).sub.2 OCH.sub.2 CF.sub.3 N N(CH.sub.3).sub.2 OCH.sub.2 CF.sub.3 NCH.sub.3 OC.sub.2 H.sub.5 N CH.sub.3 OC.sub.2 H.sub.5 NCF.sub.3 OCH.sub.3 N CF.sub.3 OCH.sub.3 NOCF.sub.2 H OCH.sub.3 N OCF.sub.2 H OCH.sub.3 NCH.sub.3 OCH.sub.2 CHCH.sub.2 N CH.sub.3 OCH.sub.2 CHCH.sub.2 N__________________________________________________________________________R = H, R.sup.4 = H, R.sup.71 = H, R = H, R.sup.4 = H, R.sup.1 = CH.sub.3,R.sup.1 = CH.sub.3, R.sup.2 = SCH.sub.3 R.sup.71 = H, R.sup.2 = C(O)N(CH.sub.3).sub.2X Y Z X Y Z__________________________________________________________________________CH.sub.3 CH.sub.3 CH CH.sub.3 CH.sub.3 CHCH.sub.3 OCH.sub.3 CH CH.sub.3 OCH.sub.3 CHOCH.sub.3 OCH.sub.3 CH OCH.sub.3 OCH.sub.3 CHCl OCH.sub.3 CH Cl OCH.sub.3 CHCH.sub.3 OC.sub.2 H.sub.5 CH CH.sub.3 OC.sub.2 H.sub.5 CHC.sub.2 H.sub.5 OCH.sub.3 CH C.sub.2 H.sub.5 OCH.sub.3 CHH OCH.sub.3 CH H OCH.sub.3 CHH OC.sub.2 H.sub.5 CH H OC.sub.2 H.sub.5 CHOCH.sub.3 CH.sub.2 OCH.sub.3 CH OCH.sub.3 CH.sub.2 OCH.sub.3 CHCH.sub.3 CH(OCH.sub.3).sub.2 CH CH.sub.3 CH(OCH.sub.3).sub.2 CHOCHF.sub.2 OCH.sub.3 CH OCHF.sub.2 OCH.sub.3 CHOCH.sub.3 SCH.sub.3 CH OCH.sub.3 SCH.sub.3 CHCH.sub.3 OCH.sub.3 N CH.sub.3 OCH.sub.3 NOCH.sub.3 OCH.sub.3 N OCH.sub.3 OCH.sub.3 NNHCH.sub.3 OCH.sub.3 N NHCH.sub.3 OCH.sub.3 NN(CH.sub.3).sub.2 OCH.sub.3 N N(CH.sub.3).sub.2 OCH.sub.3 NC.sub.2 H.sub.5 OC.sub.2 H.sub.5 N C.sub.2 H.sub.5 OC.sub.2 H.sub.5 NNHCH.sub.3 OC.sub.2 H.sub.5 N NHCH.sub.3 OC.sub.2 H.sub.5 NN(CH.sub.3).sub.2 OC.sub.2 H.sub.5 N N(CH.sub.3).sub.2 OC.sub.2 H.sub.5 NNHCH.sub.3 OCH.sub.2 CF.sub.3 N NHCH.sub.3 OCH.sub.2 CF.sub.3 NN(CH.sub.3).sub.2 OCH.sub.2 CF.sub.3 N N(CH.sub.3).sub.2 OCH.sub.2 CF.sub.3 NCH.sub.3 OC.sub.2 H.sub.5 N CH.sub.3 OC.sub.2 H.sub.5 NCF.sub.3 OCH.sub.3 N CF.sub.3 OCH.sub.3 NOCF.sub.2 H OCH.sub.3 N OCF.sub.2 H OCH.sub.3 NCH.sub.3 OCH.sub.2 CHCH.sub.2 N CH.sub.3 OCH.sub.2 CHCH.sub.2 N__________________________________________________________________________R.sup.1 = CH.sub.3, R.sup.71 = H, R.sup.1 = CH.sub.2 N(CH.sub.3).sub.2, R.sup.4 = H,R.sup.2 = CH.sub.2 CH.sub.2 OCH.sub.3, R.sup.4 = H R.sup.71 = H, R.sup.2 = CO.sub.2 CH.sub.3R X Y Z R X Y Z__________________________________________________________________________H CH.sub.3 CH.sub.3 CH H CH.sub.3 CH.sub.3 CHH CH.sub.3 OCH.sub.3 CH H CH.sub.3 OCH.sub.3 CHH OCH.sub.3 OCH.sub.3 CH H OCH.sub.3 OCH.sub.3 CHH Cl OCH.sub.3 CH H Cl OCH.sub.3 CHCH.sub.3 OCH.sub.3 OCH.sub.3 CH CH.sub.3 OCH.sub.3 OCH.sub.3 CHH CH.sub.3 OCH.sub.3 N H CH.sub.3 OCH.sub.3 NH OCH.sub.3 OCH.sub.3 N H OCH.sub.3 OCH.sub.3 NH NHCH.sub.3 OC.sub.2 H.sub.5 N N NHCH.sub.3 OC.sub.2 H.sub.5 NH N(CH.sub.3).sub.2 OC.sub.2 H.sub.5 N H N(CH.sub.3).sub.2 OC.sub.2 H.sub.5 NCH.sub.3 OCH.sub.3 OCH.sub.3 N CH.sub.3 OCH.sub.3 OCH.sub.3 N__________________________________________________________________________ ##STR55##R X Y Z R X Y Z__________________________________________________________________________H CH.sub.3 CH.sub.3 CH H CH.sub.3 CH.sub.3 CHH CH.sub.3 OCH.sub.3 CH H CH.sub.3 OCH.sub.3 CHH OCH.sub.3 OCH.sub.3 CH H OCH.sub.3 OCH.sub.3 CHH Cl OCH.sub.3 CH H Cl OCH.sub.3 CHCH.sub.3 OCH.sub.3 OCH.sub.3 CH CH.sub.3 OCH.sub.3 OCH.sub.3 CHH CH.sub.3 OCH.sub.3 N H CH.sub.3 OCH.sub.3 NH OCH.sub.3 OCH.sub.3 N H OCH.sub.3 OCH.sub.3 NH NHCH.sub.3 OC.sub.2 H.sub.5 N N NHCH.sub.3 OC.sub.2 H.sub.5 NH N(CH.sub.3).sub.2 OC.sub.2 H.sub.5 N H N(CH.sub.3).sub.2 OC.sub.2 H.sub.5 NCH.sub.3 OCH.sub.3 OCH.sub.3 N CH.sub.3 OCH.sub.3 OCH.sub.3 N__________________________________________________________________________R.sup.1 = H, R.sup.71 = H, R.sup.1 = H, R.sup.4 = H, R.sup.71 = H,R.sup.2 = CO.sub.2 CH.sub.3, R.sup.4 = H R.sup.2 = SO.sub.2 N(CH.sub.3).sub.2R X Y Z R X Y Z__________________________________________________________________________H CH.sub.3 CH.sub.3 CH H CH.sub.3 CH.sub.3 CHH CH.sub.3 OCH.sub.3 CH H CH.sub.3 OCH.sub.3 CHH OCH.sub.3 OCH.sub.3 CH H OCH.sub.3 OCH.sub.3 CHH Cl OCH.sub.3 CH H Cl OCH.sub.3 CHCH.sub.3 OCH.sub.3 OCH.sub.3 CH CH.sub.3 OCH.sub.3 OCH.sub.3 CHH CH.sub.3 OCH.sub.3 N H CH.sub.3 OCH.sub.3 NH OCH.sub.3 OCH.sub.3 N H OCH.sub.3 OCH.sub.3 NH NHCH.sub.3 OC.sub.2 H.sub.5 N N NHCH.sub.3 OC.sub.2 H.sub.5 NH N(CH.sub.3).sub.2 OC.sub.2 H.sub.5 N H N(CH.sub.3).sub.2 OC.sub.2 H.sub.5 NCH.sub.3 OCH.sub.3 OCH.sub.3 N CH.sub.3 OCH.sub.3 OCH.sub.3 N__________________________________________________________________________R.sup.1 = R.sup.4 = H, R.sup.71 = H, R.sup.1 = R.sup.4 = H, R.sup.71 = H,R.sup.2 = CHO R.sup.2 = CO.sub.2 EtR X Y Z R X Y Z__________________________________________________________________________H CH.sub.3 CH.sub.3 CH H CH.sub.3 CH.sub.3 CHH CH.sub.3 OCH.sub.3 CH H CH.sub.3 OCH.sub.3 CHH OCH.sub.3 OCH.sub.3 CH H OCH.sub.3 OCH.sub.3 CHH Cl OCH.sub.3 CH H Cl OCH.sub.3 CHCH.sub.3 OCH.sub.3 OCH.sub.3 CH CH.sub.3 OCH.sub.3 OCH.sub.3 CHH CH.sub.3 OCH.sub.3 N H CH.sub.3 OCH.sub.3 NH OCH.sub.3 OCH.sub.3 N H OCH.sub.3 OCH.sub.3 NH NHCH.sub.3 OC.sub.2 H.sub.5 N N NHCH.sub.3 OC.sub.2 H.sub.5 NH N(CH.sub.3).sub.2 OC.sub.2 H.sub.5 N H N(CH.sub.3).sub.2 OC.sub.2 H.sub.5 NCH.sub.3 OCH.sub.3 OCH.sub.3 N CH.sub.3 OCH.sub.3 OCH.sub.3 N__________________________________________________________________________X = Y = OCH.sub.3, Z = CH, R = H, R.sup.71 = HR.sup.1 R.sup.2 R.sup.4__________________________________________________________________________CH.sub.2 SCH.sub.3 CO.sub.2 CH.sub.3 BrCH.sub.2 CH.sub.2 OCH.sub.3 CO.sub.2 CH.sub.3 HCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CO.sub.2 CH.sub.3 Hc-C.sub.5 H.sub.9 SO.sub.2 N(CH.sub.3).sub.2 FCH.sub.2 CF.sub.3 SO.sub.2 N(CH.sub.3).sub.2 HCH.sub.2 CH.sub.2 CH.sub.2 Cl SO.sub.2 N(CH.sub.3).sub.2 HCH.sub.2 CHCH.sub.2 SCH.sub.3 ClCO.sub.2 -t-Bu SCH.sub.3 BrN(CH.sub.3).sub.2 SCH.sub.3 HC(O)N(CH.sub.3).sub.2 SO.sub.2 CH.sub.3 H ##STR56## SO.sub.2 CH.sub.3 BrC(O)-n-Pr SO.sub.2 CH.sub.3 HCO.sub.2 CH.sub.3 CH.sub.3 FCH.sub.3 CO.sub.2 CH.sub.3 CO.sub.2 CH.sub.3CH.sub.3 CH.sub.2 SO.sub.2 N(CH.sub.3).sub.2 CO.sub.2 CH.sub.3CH.sub.3 n-Bu BrCH.sub.2 SCH.sub.3 CH.sub.2 CO.sub.2 CH.sub.3 CH.sub.3CH.sub.3 CH.sub.2 CH.sub.2 CO.sub.2 CH.sub.3 HCH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3 HCH.sub.3 CH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.3 HCH.sub.2 CH.sub.2 F CH.sub.2 SO.sub.2 CH.sub.2 CH.sub.3 HCH.sub.3 CH.sub.2 OH EtH CH.sub.2 Br CO.sub.2 CH.sub.2 CH.sub.3H CH.sub.2 Cl FEt CHF.sub.2 EtCH.sub.3 ##STR57## H__________________________________________________________________________X = CH.sub.3, Y = OCH.sub.3, Z = N, R = H, R.sup.1 = CH.sub.3,R.sup.4 = H, R.sup.2 = (CH.sub.2).sub.m Q.sup.2, R.sup.71 = Hm Q.sup.2 R.sup.45 R.sup.46 R.sup.47 R.sup.48__________________________________________________________________________0 Q.sup.2 -1 H H -- --1 Q.sup.2 -1 H H -- --0 Q.sup.2 -1 4-Cl H -- --0 Q.sup.2 -1 4-CH.sub.3 H -- --0 Q.sup.2 -1 4-CH.sub.3 2-Cl -- --1 Q.sup.2 -1 2-Cl 4-Cl -- --0 Q.sup.2 -1 3-Cl 4-Cl -- --0 Q.sup.2 -2 -- -- CH.sub.3 CH.sub.30 Q.sup.2 -2 -- -- n-Pr H0 Q.sup.2 -2 -- -- Et H0 Q.sup.2 -3 -- -- H --0 Q.sup.2 -3 -- -- CH.sub.3 --0 Q.sup.2 -3 -- -- Et --__________________________________________________________________________X = OCH.sub.3, Y = OCH.sub.3, Z = N, R = H,R.sup.1 = CH.sub.3, R.sup.4 = H, R.sup.2 = (CH.sub.2).sub.m Q.sup.2,R.sup.71 = Hm r Q.sup.2 R.sup.49 R.sup.50 R.sup.51 R.sup.52 R.sup.53 R.sup.54 R.sup.55__________________________________________________________________________0 0 Q.sup.2 -4 H H -- -- -- -- --0 1 Q.sup.2 -4 4-CH.sub.3 H -- -- -- -- --0 0 Q.sup.2 -4 5-CH.sub.3 H -- -- -- -- --0 0 Q.sup.2 -4 4-CH.sub.3 6-CH.sub.3 -- -- -- -- --0 1 Q.sup.2 -4 6-CH.sub.3 H -- -- -- -- --0 1 Q.sup.2 -5 H H -- -- -- -- --0 0 Q.sup.2 -5 6-CH.sub.3 H -- -- -- -- --0 0 Q.sup.2 -5 5-CH.sub.3 H -- -- -- -- --0 1 Q.sup.2 -6 H H -- -- -- -- --0 0 Q.sup.2 -6 2-CH.sub.3 H -- -- -- -- --0 -- Q.sup.2 -7 -- -- H H H -- --1 -- Q.sup.2 -7 -- -- CH.sub.3 H OCH.sub.3 -- --0 -- Q.sup.2 -7 -- -- OCH.sub.3 H H -- --0 -- Q.sup.2 -7 -- -- H CH.sub.3 H -- --0 -- Q.sup.2 -8 -- -- -- -- -- H H0 -- Q.sup.2 -9 -- -- -- -- -- 2-CH.sub.3 H__________________________________________________________________________X = Y = OCH.sub.3, Z = CH, R = R.sup.4 = H,R.sup.1 = CH.sub.3, R.sup.2 = (CH.sub.2).sub.m Q.sup.2, R.sup.71 = Hm Q.sup.2 W.sup.3 R.sup.56 R.sup.57 R.sup.58__________________________________________________________________________0 Q.sup.2 -10 O H H H0 Q.sup.2 -10 O H H OCH.sub.30 Q.sup.2 -10 O H CH.sub.3 H0 Q.sup.2 -10 S H H H0 Q.sup.2 -10 S CH.sub.3 H H1 Q.sup.2 -10 S H H OEt0 Q.sup.2 -10 S Cl H H0 Q.sup.2 -10 S H H Et0 Q.sup.2 -10 S H H Br0 Q.sup.2 -11 O H H H0 Q.sup.2 -11 O H H CH.sub.30 Q.sup.2 -11 O CH.sub.3 H H0 Q.sup.2 -11 S H H H0 Q.sup.2 -11 S H CH.sub.3 H0 Q.sup.2 -11 S H H Cl__________________________________________________________________________X = CH.sub.3, Y = OCH.sub.3, Z = CH, R = R.sup.4 = H,R.sup.1 = CH.sub.3, R.sup.2 = (CH.sub.2).sub.m Q.sup.2, m = O, R.sup.71 =Q.sup.2 W.sup.4 R.sup.59 R.sup.60 R.sup.61 R.sup.62 R.sup.63 R.sup.64 R.sup.65__________________________________________________________________________Q.sup.2 -12 -- H CH.sub.3 -- -- -- -- --Q.sup.2 -12 -- CH.sub.3 CH.sub.3 -- -- -- -- --Q.sup.2 -13 -- -- -- H -- -- -- --Q.sup.2 -13 -- -- -- CH.sub.3 -- -- -- --Q.sup.2 -13 -- -- -- OCH.sub.3 -- -- -- --Q.sup.2 -14 -- -- -- H -- -- -- --Q.sup.2 -14 -- -- -- OCH.sub.3 -- -- -- --Q.sup.2 -15 -- -- -- -- H -- -- --Q.sup.2 -15 -- -- -- -- Et -- -- --Q.sup.2 -16 -- -- -- -- H -- -- --Q.sup.2 -16 -- -- -- -- CH.sub.3 -- -- --Q.sup.2 -17 NH -- -- -- -- H H --Q.sup.2 -17 NCH.sub.3 -- -- -- H H H --Q.sup.2 -18 NCH.sub.3 -- -- -- -- H H --Q.sup.2 -19 NH -- -- SCH.sub.3 -- -- H --Q.sup.2 -19 NCH.sub.3 -- -- OCH.sub.3 -- -- H --Q.sup.2 -20 -- -- -- -- -- -- -- HQ.sup.2 -20 -- -- -- -- -- -- -- CH.sub.3Q.sup.2 -20 -- -- -- -- -- -- -- OEtQ.sup.2 -21 -- -- -- -- -- -- -- EtQ.sup.2 -21 -- -- -- -- -- -- -- HQ.sup.2 -21 -- -- -- -- -- -- -- OCH.sub.3__________________________________________________________________________X = Y = OCH.sub.3, Z = CH, R = R.sup.4 = H,R.sup.2 = CO.sub.2 CH.sub.3, R.sup.71 = HQ.sup.1 -1 R.sup.25 = R.sup.26 = HQ.sup.1 -1 R.sup.25 = 4-Cl, R.sup.26 = HQ.sup.1 -2 q = O, R.sup.27 = R.sup.28 -HQ.sup.1 -3 q = O, R.sup.27 = 6-CH.sub.3, R.sup.28 = HQ.sup.1 -4 q = O, R.sup.27 = R.sup.28 = HQ.sup.1 -5 R.sup.29 = R.sup.30 = R.sup.31 = HQ.sup.1 -6 R.sup.32 = R.sup.33 = HQ.sup.1 -8 W.sup.1 = O, R.sup.34 = R.sup.35 = R.sup.36 = HQ.sup.1 -8 W.sup.1 = S, R.sup.34 = R.sup.35 = R.sup.36 = HQ.sup.1 -9 W.sup.1 = S, R.sup.34 = R.sup.35 = R.sup.36 = HQ.sup.1 -10 R.sup.37 = H, R.sup.38 = CH.sub.3Q.sup.1 -11 R.sup.39 = SCH.sub.3Q.sup.1 -15 W.sup.2 = S, R.sup.63 = R.sup.64 = HQ.sup.1 -21 R.sup.65 = CH.sub.3__________________________________________________________________________
TABLE 2__________________________________________________________________________ ##STR58##R = H, R.sup.1 = CH.sub.3, R.sup.2 = SO.sub.2 N(CH.sub.3).sub.2, R.sup.4= H, R.sup.71 = HX Y Z X Y Z__________________________________________________________________________CH.sub.3 CH.sub.3 CH NHCH.sub.3 OCH.sub.3 NCH.sub.3 OCH.sub.3 CH N(CH.sub.3).sub.2 OCH.sub.3 NOCH.sub.3 OCH.sub.3 CH C.sub.2 H.sub.5 OC.sub.2 H.sub.5 NCl OCH.sub.3 CH NHCH.sub.3 OC.sub.2 H.sub.5 NCH.sub.3 OC.sub.2 H.sub.5 CH N(CH.sub.3).sub.2 OC.sub.2 H.sub.5 NC.sub.2 H.sub.5 OCH.sub.3 CH NHCH.sub.3 OCH.sub.2 CF.sub.3 NH OCH.sub.3 CH N(CH.sub.3).sub.2 OCH.sub.2 CF.sub.3 NH OC.sub.2 H.sub.5 CH CH.sub.3 OC.sub.2 H.sub.5 NOCH.sub.3 CH.sub.2 OCH.sub.3 CH CF.sub.3 OCH.sub.3 NCH.sub.3 CH(OCH.sub.3).sub.2 CH OCF.sub.2 H OCH.sub.3 NOCHF.sub.2 OCH.sub.3 CH CH.sub.3 OCH.sub.2 CHCH.sub.2 NOCH.sub.3 SCH.sub.3 CHCH.sub.3 OCH.sub.3 NOCH.sub.3 OCH.sub.3 N__________________________________________________________________________Z = CHX Y X Y__________________________________________________________________________(CH.sub.2).sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CH.sub.2 SO.sub.2 CH.sub.3iPr OCH.sub.3 OCH.sub.3 cBu(CH.sub.2).sub.4 Cl OCH.sub.3 CH.sub.3 O(CH.sub.2).sub.2 CHCH.sub.2SEt SEt SCH.sub.2 CF.sub.3 OCH.sub.3S(CH.sub.2).sub.3 CH.sub.3 OCH.sub.3 SCHF.sub.2 CH.sub.3OCH.sub.2 OEt CH.sub.3 CF.sub.3 CF.sub.3O(CH.sub.2).sub.2 OiPr OCH.sub.3 CH.sub.2 Cl OCH.sub.3O(CH.sub.2).sub.2 OCH.sub.3 OC.sub.2 H.sub.5 CH.sub.2 Br OCH.sub.3CH.sub.2 CH.sub.2 OCH.sub.3 Et CH.sub.2 F OEtH H I OCH.sub.3Cl N(CH.sub.3).sub.2 OCH.sub.2 CHF.sub.2 CH.sub.3Br NHCH.sub.3 NHiPr CH.sub.3OCH.sub.3 CN N(iPr).sub.2 CH.sub.3CH.sub.3 CH.sub.2 CCH OCH.sub.2 CF.sub.3 OCH.sub.2 CF.sub.3CH.sub.3 OCH.sub.2 CCH NEt.sub.2 NEt.sub.2OCH.sub.3 OCH.sub.2 CHCH.sub.2 OCH.sub.3 N.sub.3NEt.sub.2 OCH.sub.3 CH.sub.3 cPrOCH.sub.2 iPr OCH.sub.3 CH.sub.3 CH.sub.2 SEtNH.sub.2 CH.sub.3 OCH.sub.3 cC.sub.5 H.sub.9N(CH.sub.3)Et OCH.sub.3 O(CH.sub.2).sub.3 Cl O(CH.sub.2).sub.3 ClCl OC.sub.2 H.sub.5Br OCH.sub.3OCF.sub.2 H OCF.sub.2 HOCH.sub.2 CF.sub.3 OCF.sub.2 HOCH.sub.2 CF.sub.3 CH.sub.3OCH.sub.2 CH.sub.2 CH.sub.2 F OCH.sub.3OiPr OCH.sub.3CH.sub.3 N(OCH.sub.3)CH.sub.3O(CH.sub.2).sub.3 CH.sub.3 O(CH.sub.2).sub.3 CH.sub.3iPr iPrOCH.sub.3 cPr__________________________________________________________________________R.sup.2 = CO.sub.2 CH.sub.3, R.sup.71 = H, R = R.sup.4 = H, R = H, R.sup.1 = CH.sub.3, R.sup.71 = H,R.sup.1 = CH.sub.3 R.sup.2 = CO.sub.2 C.sub.2 H.sub.5, R.sup.4 = HX Y Z X Y Z__________________________________________________________________________CH.sub.3 CH.sub.3 CH CH.sub.3 CH.sub.3 CHCH.sub.3 OCH.sub.3 CH CH.sub.3 OCH.sub.3 CHOCH.sub.3 OCH.sub.3 CH OCH.sub.3 OCH.sub.3 CHCl OCH.sub.3 CH Cl OCH.sub.3 CHCH.sub.3 OC.sub.2 H.sub.5 CH CH.sub.3 OC.sub.2 H.sub.5 CHC.sub.2 H.sub.5 OCH.sub.3 CH C.sub.2 H.sub.5 OCH.sub.3 CHH OCH.sub.3 CH H OCH.sub.3 CHH OC.sub.2 H.sub.5 CH H OC.sub.2 H.sub.5 CHOCH.sub.3 CH.sub.2 OCH.sub.3 CH OCH.sub.3 CH.sub.2 OCH.sub.3 CHCH.sub.3 CH(OCH.sub.3).sub.2 CH CH.sub.3 CH(OCH.sub.3).sub.2 CHOCHF.sub.2 OCH.sub.3 CH OCHF.sub.2 OCH.sub.3 CHOCH.sub.3 SCH.sub.3 CH OCH.sub.3 SCH.sub.3 CHCH.sub.3 OCH.sub.3 N CH.sub.3 OCH.sub.3 NOCH.sub.3 OCH.sub.3 N OCH.sub.3 OCH.sub.3 NNHCH.sub.3 OCH.sub.3 N NHCH.sub.3 OCH.sub.3 NN(CH.sub.3).sub.2 OCH.sub.3 N N(CH.sub.3).sub.2 OCH.sub.3 NC.sub.2 H.sub.5 OC.sub.2 H.sub.5 N C.sub.2 H.sub.5 OC.sub.2 H.sub.5 NNHCH.sub.3 OC.sub.2 H.sub.5 N NHCH.sub.3 OC.sub.2 H.sub.5 NN(CH.sub.3).sub.2 OC.sub.2 H.sub.5 N N(CH.sub.3).sub.2 OC.sub.2 H.sub.5 NNHCH.sub.3 OCH.sub.2 CF.sub.3 N NHCH.sub.3 OCH.sub.2 CF.sub.3 NN(CH.sub.3).sub.2 OCH.sub.2 CF.sub.3 N N(CH.sub.3).sub.2 OCH.sub.2 CF.sub.3 NCH.sub.3 OC.sub.2 H.sub.5 N CH.sub.3 OC.sub.2 H.sub.5 NCF.sub.3 OCH.sub.3 N CF.sub.3 OCH.sub.3 NOCF.sub.2 H OCH.sub.3 N OCF.sub.2 H OCH.sub.3 NCH.sub.3 OCH.sub.2 CHCH.sub.2 N CH.sub.3 OCH.sub.2 CHCH.sub.2 N__________________________________________________________________________R = R.sup.4 = H, R.sup.71 = H, R.sup.2 =SO.sub.2 CH.sub.3, R = R.sup.4 = H, R.sup.1 = CH.sub.3, R.sup.2 = Br,R.sup.1 = CH.sub.3 R.sup.71 = HX Y Z X Y Z__________________________________________________________________________CH.sub.3 CH.sub.3 CH CH.sub.3 CH.sub.3 CHCH.sub.3 OCH.sub.3 CH CH.sub.3 OCH.sub.3 CHOCH.sub.3 OCH.sub.3 CH OCH.sub.3 OCH.sub.3 CHCl OCH.sub.3 CH Cl OCH.sub.3 CHCH.sub.3 OC.sub.2 H.sub.5 CH CH.sub.3 OC.sub.2 H.sub.5 CHC.sub.2 H.sub.5 OCH.sub.3 CH C.sub.2 H.sub.5 OCH.sub.3 CHH OCH.sub.3 CH H OCH.sub.3 CHH OC.sub.2 H.sub.5 CH H OC.sub.2 H.sub.5 CHOCH.sub.3 CH.sub.2 OCH.sub.3 CH OCH.sub.3 CH.sub.2 OCH.sub.3 CHCH.sub.3 CH(OCH.sub.3).sub.2 CH CH.sub.3 CH(OCH.sub.3).sub.2 CHOCHF.sub.2 OCH.sub.3 CH OCHF.sub.2 OCH.sub.3 CHOCH.sub.3 SCH.sub.3 CH OCH.sub.3 SCH.sub.3 CHCH.sub.3 OCH.sub.3 N CH.sub.3 OCH.sub.3 NOCH.sub.3 OCH.sub.3 N OCH.sub.3 OCH.sub.3 NNHCH.sub.3 OCH.sub.3 N NHCH.sub.3 OCH.sub.3 NN(CH.sub.3).sub.2 OCH.sub.3 N N(CH.sub.3).sub.2 OCH.sub.3 NC.sub.2 H.sub.5 OC.sub.2 H.sub.5 N C.sub.2 H.sub.5 OC.sub.2 H.sub.5 NNHCH.sub.3 OC.sub.2 H.sub.5 N NHCH.sub.3 OC.sub.2 H.sub.5 NN(CH.sub.3).sub.2 OC.sub.2 H.sub.5 N N(CH.sub.3).sub.2 OC.sub.2 H.sub.5 NNHCH.sub.3 OCH.sub.2 CF.sub.3 N NHCH.sub.3 OCH.sub.2 CF.sub.3 NN(CH.sub.3).sub.2 OCH.sub.2 CF.sub.3 N N(CH.sub.3).sub.2 OCH.sub.2 CF.sub.3 NCH.sub.3 OC.sub.2 H.sub.5 N CH.sub.3 OC.sub.2 H.sub.5 NCF.sub.3 OCH.sub.3 N CF.sub.3 OCH.sub.3 NOCF.sub.2 H OCH.sub.3 N OCF.sub.2 H OCH.sub.3 NCH.sub.3 OCH.sub.2 CHCH.sub.2 N CH.sub.3 OCH.sub.2 CHCH.sub.2 N__________________________________________________________________________R.sup.1 = CH.sub.3, R.sup.4 = H, R.sup.71 = H, R.sup.1 = CH.sub.3, R.sup.4 = H, R.sup.71 = H,R.sup.2 = C(O)CH.sub.3 R.sup.2 = C(H)NOCH.sub.3R X Y Z R X Y Z__________________________________________________________________________H CH.sub.3 CH.sub.3 CH H CH.sub.3 CH.sub.3 CHH CH.sub.3 OCH.sub.3 CH H CH.sub.3 OCH.sub.3 CHH OCH.sub.3 OCH.sub.3 CH H OCH.sub.3 OCH.sub.3 CHH Cl OCH.sub.3 CH H Cl OCH.sub.3 CHCH.sub.3 OCH.sub.3 OCH.sub.3 CH CH.sub.3 OCH.sub.3 OCH.sub.3 CHH CH.sub.3 OCH.sub.3 N H CH.sub.3 OCH.sub.3 NH OCH.sub.3 OCH.sub.3 N H OCH.sub.3 OCH.sub.3 NH NHCH.sub.3 OC.sub.2 H.sub.5 N N NHCH.sub.3 OC.sub.2 H.sub.5 NH N(CH.sub.3).sub.2 OC.sub.2 H.sub.5 N H N(CH.sub.3).sub.2 OC.sub.2 H.sub.5 NCH.sub.3 OCH.sub.3 OCH.sub.3 N CH.sub.3 OCH.sub.3 OCH.sub.3 N__________________________________________________________________________ ##STR59## ##STR60##R X Y Z R X Y Z__________________________________________________________________________H CH.sub.3 CH.sub.3 CH H CH.sub.3 CH.sub.3 CHH CH.sub.3 OCH.sub.3 CH H CH.sub.3 OCH.sub.3 CHH OCH.sub.3 OCH.sub.3 CH H OCH.sub.3 OCH.sub.3 CHH Cl OCH.sub.3 CH H Cl OCH.sub.3 CHCH.sub.3 OCH.sub.3 OCH.sub.3 CH CH.sub.3 OCH.sub.3 OCH.sub.3 CHH CH.sub.3 OCH.sub.3 N H CH.sub.3 OCH.sub.3 NH OCH.sub.3 OCH.sub.3 N H OCH.sub.3 OCH.sub.3 NH NHCH.sub.3 OC.sub.2 H.sub.5 N N NHCH.sub.3 OC.sub.2 H.sub.5 NH N(CH.sub.3).sub.2 OC.sub.2 H.sub.5 N H N(CH.sub.3).sub.2 OC.sub.2 H.sub.5 NCH.sub.3 OCH.sub.3 OCH.sub.3 N CH.sub.3 OCH.sub.3 OCH.sub.3 N__________________________________________________________________________R.sup.1 = CH.sub.3, R.sup.4 = H, R.sup.71 = H, R.sup.1 = CH.sub.3, R.sup.4 = H, R.sup.71 = H,R.sup.2 = CHO R.sup.2 = CHF.sub.2R X Y Z R X Y Z__________________________________________________________________________H CH.sub.3 CH.sub.3 CH H CH.sub.3 CH.sub.3 CHH CH.sub.3 OCH.sub.3 CH H CH.sub.3 OCH.sub.3 CHH OCH.sub.3 OCH.sub.3 CH H OCH.sub.3 OCH.sub.3 CHH Cl OCH.sub.3 CH H Cl OCH.sub.3 CHCH.sub.3 OCH.sub.3 OCH.sub.3 CH CH.sub.3 OCH.sub.3 OCH.sub.3 CHH CH.sub.3 OCH.sub.3 N H CH.sub.3 OCH.sub.3 NH OCH.sub.3 OCH.sub.3 N H OCH.sub.3 OCH.sub.3 NH NHCH.sub.3 OC.sub.2 H.sub.5 N N NHCH.sub.3 OC.sub.2 H.sub.5 NH N(CH.sub.3).sub.2 OC.sub.2 H.sub.5 N H N(CH.sub.3).sub.2 OC.sub.2 H.sub.5 NCH.sub.3 OCH.sub.3 OCH.sub.3 N CH.sub.3 OCH.sub.3 OCH.sub.3 N__________________________________________________________________________R.sup.1 = CH.sub.3, R.sup.4 = H, R.sup.71 = H, R.sup.1 = CH.sub.3, R.sup.4 = H, R.sup.71 = H,R.sup.2 = CH.sub.2 OCH.sub.3 R.sup.2 = CH.sub.2 CNR X Y Z R X Y Z__________________________________________________________________________H CH.sub.3 CH.sub.3 CH H CH.sub.3 CH.sub.3 CHH CH.sub.3 OCH.sub.3 CH H CH.sub.3 OCH.sub.3 CHH OCH.sub.3 OCH.sub.3 CH H OCH.sub.3 OCH.sub.3 CHH Cl OCH.sub.3 CH H Cl OCH.sub.3 CHCH.sub.3 OCH.sub.3 OCH.sub.3 CH CH.sub.3 OCH.sub.3 OCH.sub.3 CHH CH.sub.3 OCH.sub.3 N H CH.sub.3 OCH.sub.3 NH OCH.sub.3 OCH.sub.3 N H OCH.sub.3 OCH.sub.3 NH NHCH.sub.3 OC.sub.2 H.sub.5 N N NHCH.sub.3 OC.sub.2 H.sub.5 NH N(CH.sub.3).sub.2 OC.sub.2 H.sub.5 N H N(CH.sub.3).sub.2 OC.sub.2 H.sub.5 NCH.sub.3 OCH.sub.3 OCH.sub.3 N CH.sub.3 OCH.sub.3 OCH.sub.3 N__________________________________________________________________________X = Y = OCH.sub.3, Z = CH, R = H, R.sup.71 = HR.sup.1 R.sup.2 R.sup.4__________________________________________________________________________CH.sub.3 S(O)CH.sub.3 CO.sub.2 CH.sub.3H S(O)CH.sub.3 HCH.sub.2 OCH.sub.3 CH.sub.2 CO.sub.2 CH.sub.3 HCH.sub.3 CH.sub.2 OH ClH CH.sub.2 OH CH.sub.3CH.sub.3 CH.sub.2 Cl BrCH.sub.3 ##STR61## HCH.sub.3 CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3 ClCO.sub.2 -t-Bu Cl HC(O)NH-t-Bu Br HC(O)Et n-Pr Hc-C.sub.6 H.sub.11 CHF.sub.2 HCH.sub.2 CH.sub.2 Cl CO.sub.2 Et BrEt CH(OCH.sub.3).sub.2 CH.sub.3CH.sub.3 C(O)N(CH.sub.3).sub.2 HCH.sub.2 OCH.sub.3 C(O)N(CH.sub.3).sub.2 HCH.sub.2 CHCH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3 HCH.sub.2 N(CH.sub.3).sub.2 CH.sub.2 CO.sub.2 CH.sub.3 HCH.sub.2 SCH.sub.3 CO.sub.2 CH.sub.2 OCH.sub.3 HCH.sub.2 - c-Pr S(O)CH.sub.2 CHCH.sub.2 HCH.sub.2 CF.sub.2 H NO.sub.2 HCH.sub.2 CH.sub.2 C(OCH.sub.3)CH.sub.3 CH.sub.2 CH.sub.2 CN HCH.sub.3 CH.sub.2 C.sub.6 H.sub.5 BrCH.sub.3 CN HCH.sub.3 CH.sub.2 CH.sub.2 C(O)CH.sub.3 H__________________________________________________________________________
TABLE 3__________________________________________________________________________ ##STR62##R = H, R.sup.1 = CH.sub.3, R.sup.2 = CO.sub.2 CH.sub.3, R.sup.3 = H,R.sup.71 = HX Y Z X Y Z__________________________________________________________________________CH.sub.3 CH.sub.3 CH NHCH.sub.3 OCH.sub.3 NCH.sub.3 OCH.sub.3 CH N(CH.sub.3).sub.2 OCH.sub.3 NOCH.sub.3 OCH.sub.3 CH C.sub.2 H.sub.5 OC.sub.2 H.sub.5 NCl OCH.sub.3 CH NHCH.sub.3 OC.sub.2 H.sub.5 NCH.sub.3 OC.sub.2 H.sub.5 CH N(CH.sub.3).sub.2 OC.sub.2 H.sub.5 NC.sub.2 H.sub.5 OCH.sub.3 CH NHCH.sub.3 OCH.sub.2 CF.sub.3 NH OCH.sub.3 CH N(CH.sub.3).sub.2 OCH.sub.2 CF.sub.3 NH OC.sub.2 H.sub.5 CH CH.sub.3 OC.sub.2 H.sub.5 NOCH.sub.3 CH.sub.2 OCH.sub.3 CH CF.sub.3 OCH.sub.3 NCH.sub.3 CH(OCH.sub.3).sub.2 CH OCF.sub.2 H OCH.sub.3 NOCHF.sub.2 OCH.sub.3 CH CH.sub.3 OCH.sub.2 CHCH.sub.2 NOCH.sub.3 SCH.sub.3 CHCH.sub.3 OCH.sub.3 NOCH.sub.3 OCH.sub.3 N__________________________________________________________________________Z = CHX Y X Y__________________________________________________________________________(CH.sub.2).sub.3 CH.sub.3 OCH.sub.3 OCH.sub.3 CH.sub.2 SO.sub.2 CH.sub.3iPr OCH.sub.3 OCH.sub.3 cBu(CH.sub.2).sub.4 Cl OCH.sub.3 CH.sub.3 O(CH.sub.2).sub.2 CHCH.sub.2SEt SEt SCH.sub.2 CF.sub.3 OCH.sub.3S(CH.sub.2).sub.3 CH.sub.3 OCH.sub.3 SCHF.sub.2 CH.sub.3OCH.sub.2 OEt CH.sub.3 CF.sub.3 CF.sub.3O(CH.sub.2).sub.2 OiPr OCH.sub.3 CH.sub.2 Cl OCH.sub.3O(CH.sub.2).sub.2 OCH.sub.3 OC.sub.2 H.sub.5 CH.sub.2 Br OCH.sub.3CH.sub.2 CH.sub.2 OCH.sub.3 Et CH.sub.2 F OEtH H I OCH.sub.3Cl N(CH.sub.3).sub.2 OCH.sub.2 CHF.sub.2 CH.sub.3Br NHCH.sub.3 NHiPr CH.sub.3OCH.sub.3 CN N(iPr).sub.2 CH.sub.3CH.sub.3 CH.sub.2 CCH OCH.sub.2 CF.sub.3 OCH.sub.2 CF.sub.3CH.sub.3 OCH.sub.2 CCH NEt.sub.2 NEt.sub.2OCH.sub.3 OCH.sub.2 CHCH.sub.2 OCH.sub.3 N.sub.3NEt.sub.2 OCH.sub.3 CH.sub.3 cPrOCH.sub.2 iPr OCH.sub.3 CH.sub.3 CH.sub.2 SEtNH.sub.2 CH.sub.3 OCH.sub.3 cC.sub.5 H.sub.9N(CH.sub.3)Et OCH.sub.3 O(CH.sub.2).sub.3 Cl O(CH.sub.2).sub.3 ClCl OC.sub.2 H.sub.5Br OCH.sub.3OCF.sub.2 H OCF.sub.2 HOCH.sub.2 CF.sub.3 OCF.sub.2 HOCH.sub.2 CF.sub.3 CH.sub.3OCH.sub.2 CH.sub.2 CH.sub.2 F OCH.sub.3OiPr OCH.sub.3CH.sub.3 N(OCH.sub.3)CH.sub.3O(CH.sub.2).sub.3 CH.sub.3 O(CH.sub.2).sub.3 CH.sub.3iPr iPrOCH.sub.3 cPr__________________________________________________________________________R = R.sup.3 = H, R.sup.71 = H, R = H, R.sup.1 = CH.sub.3, R.sup.71 = Cl,R.sup.1 = CH.sub.2 OCH.sub.2 CH.sub.3, R.sup.2 = CO.sub.2 Et R.sup.3 = H, R.sup.2 = CO.sub.2 EtX Y Z X Y Z__________________________________________________________________________CH.sub.3 CH.sub.3 CH CH.sub.3 CH.sub.3 CHCH.sub.3 OCH.sub.3 CH CH.sub.3 OCH.sub.3 CHOCH.sub.3 OCH.sub.3 CH OCH.sub.3 OCH.sub.3 CHCl OCH.sub.3 CH Cl OCH.sub.3 CHCH.sub.3 OC.sub.2 H.sub.5 CH CH.sub.3 OC.sub.2 H.sub.5 CHC.sub.2 H.sub.5 OCH.sub.3 CH C.sub.2 H.sub.5 OCH.sub.3 CHH OCH.sub.3 CH H OCH.sub.3 CHH OC.sub.2 H.sub.5 CH H OC.sub.2 H.sub.5 CHOCH.sub.3 CH.sub.2 OCH.sub.3 CH OCH.sub.3 CH.sub.2 OCH.sub.3 CHCH.sub.3 CH(OCH.sub.3).sub.2 CH CH.sub.3 CH(OCH.sub.3).sub.2 CHOCHF.sub.2 OCH.sub.3 CH OCHF.sub.2 OCH.sub.3 CHOCH.sub.3 SCH.sub.3 CH OCH.sub.3 SCH.sub.3 CHCH.sub.3 OCH.sub.3 N CH.sub.3 OCH.sub.3 NOCH.sub.3 OCH.sub.3 N OCH.sub.3 OCH.sub.3 NNHCH.sub.3 OCH.sub.3 N NHCH.sub.3 OCH.sub.3 NN(CH.sub.3).sub.2 OCH.sub.3 N N(CH.sub.3).sub.2 OCH.sub.3 NC.sub.2 H.sub.5 OC.sub.2 H.sub.5 N C.sub.2 H.sub.5 OC.sub.2 H.sub.5 NNHCH.sub.3 OC.sub.2 H.sub.5 N NHCH.sub.3 OC.sub.2 H.sub.5 NN(CH.sub.3).sub.2 OC.sub.2 H.sub.5 N N(CH.sub.3).sub.2 OC.sub.2 H.sub.5 NNHCH.sub.3 OCH.sub.2 CF.sub.3 N NHCH.sub.3 OCH.sub.2 CF.sub.3 NN(CH.sub.3).sub.2 OCH.sub.2 CF.sub.3 N N(CH.sub.3).sub.2 OCH.sub.2 CF.sub.3 NCH.sub.3 OC.sub.2 H.sub.5 N CH.sub.3 OC.sub.2 H.sub.5 NCF.sub.3 OCH.sub.3 N CF.sub.3 OCH.sub.3 NOCF.sub.2 H OCH.sub.3 N OCF.sub.2 H OCH.sub.3 NCH.sub.3 OCH.sub.2 CHCH.sub.2 N CH.sub.3 OCH.sub.2 CHCH.sub.2 N__________________________________________________________________________R = R.sup.3 = H, R.sup.71 = H, R.sup.1 = CH.sub.3, R = R.sup.3 = H, R.sup.1 = CH.sub.3, R.sup.71 = H,R.sup.2 = SO.sub.2 CH.sub.3 R.sup.2 = SO.sub.2 N(CH.sub.3).sub.2X Y Z X Y Z__________________________________________________________________________CH.sub.3 CH.sub.3 CH CH.sub.3 CH.sub.3 CHCH.sub.3 OCH.sub.3 CH CH.sub.3 OCH.sub.3 CHOCH.sub.3 OCH.sub.3 CH OCH.sub.3 OCH.sub.3 CHCl OCH.sub.3 CH Cl OCH.sub.3 CHCH.sub.3 OC.sub.2 H.sub.5 CH CH.sub.3 OC.sub.2 H.sub.5 CHC.sub.2 H.sub.5 OCH.sub.3 CH C.sub.2 H.sub.5 OCH.sub.3 CHH OCH.sub.3 CH H OCH.sub.3 CHH OC.sub.2 H.sub.5 CH H OC.sub.2 H.sub.5 CHOCH.sub.3 CH.sub.2 OCH.sub.3 CH OCH.sub.3 CH.sub.2 OCH.sub.3 CHCH.sub.3 CH(OCH.sub.3).sub.2 CH CH.sub.3 CH(OCH.sub.3).sub.2 CHOCHF.sub.2 OCH.sub.3 CH OCHF.sub.2 OCH.sub.3 CHOCH.sub.3 SCH.sub.3 CH OCH.sub.3 SCH.sub.3 CHCH.sub.3 OCH.sub.3 N CH.sub.3 OCH.sub.3 NOCH.sub.3 OCH.sub.3 N OCH.sub.3 OCH.sub.3 NNHCH.sub.3 OCH.sub.3 N NHCH.sub.3 OCH.sub.3 NN(CH.sub.3).sub.2 OCH.sub.3 N N(CH.sub.3).sub.2 OCH.sub.3 NC.sub.2 H.sub.5 OC.sub.2 H.sub.5 N C.sub.2 H.sub.5 OC.sub.2 H.sub.5 NNHCH.sub.3 OC.sub.2 H.sub.5 N NHCH.sub.3 OC.sub.2 H.sub.5 NN(CH.sub.3).sub.2 OC.sub.2 H.sub.5 N N(CH.sub.3).sub.2 OC.sub.2 H.sub.5 NNHCH.sub.3 OCH.sub.2 CF.sub.3 N NHCH.sub.3 OCH.sub.2 CF.sub.3 NN(CH.sub.3).sub.2 OCH.sub.2 CF.sub.3 N N(CH.sub.3).sub.2 OCH.sub.2 CF.sub.3 NCH.sub.3 OC.sub.2 H.sub.5 N CH.sub.3 OC.sub.2 H.sub.5 NCF.sub.3 OCH.sub.3 N CF.sub.3 OCH.sub.3 NOCF.sub.2 H OCH.sub.3 N OCF.sub.2 H OCH.sub.3 NCH.sub.3 OCH.sub.2 CHCH.sub.2 N CH.sub.3 OCH.sub.2 CHCH.sub.2 N__________________________________________________________________________ R = R.sup.3 = H, R.sup.1 = CH.sub.3, R.sup.71 = H,R = R.sup.3 = H, R.sup.71 = R.sup.2 = C(O)CH.sub.3 R.sup.2 = C(OCH.sub.3)NOCH.sub.3X Y Z X Y Z__________________________________________________________________________CH.sub.3 CH.sub.3 CH CH.sub.3 CH.sub.3 CHCH.sub.3 OCH.sub.3 CH CH.sub.3 OCH.sub.3 CHOCH.sub.3 OCH.sub.3 CH OCH.sub.3 OCH.sub.3 CHCl OCH.sub.3 CH Cl OCH.sub.3 CHCH.sub.3 OC.sub.2 H.sub.5 CH CH.sub.3 OC.sub.2 H.sub.5 CHC.sub.2 H.sub.5 OCH.sub.3 CH C.sub.2 H.sub.5 OCH.sub.3 CHH OCH.sub.3 CH H OCH.sub.3 CHH OC.sub.2 H.sub.5 CH H OC.sub.2 H.sub.5 CHOCH.sub.3 CH.sub.2 OCH.sub.3 CH OCH.sub.3 CH.sub.2 OCH.sub.3 CHCH.sub.3 CH(OCH.sub.3).sub.2 CH CH.sub.3 CH(OCH.sub.3).sub.2 CHOCHF.sub.2 OCH.sub.3 CH OCHF.sub.2 OCH.sub.3 CHOCH.sub.3 SCH.sub.3 CH OCH.sub.3 SCH.sub.3 CHCH.sub.3 OCH.sub.3 N CH.sub.3 OCH.sub.3 NOCH.sub.3 OCH.sub.3 N OCH.sub.5 OCH.sub.3 NNHCH.sub.3 OCH.sub.3 N NHCH.sub.3 OCH.sub.3 NN(CH.sub.3).sub.2 OCH.sub.3 N N(CH.sub.3).sub.2 OCH.sub.3 NC.sub.2 H.sub.5 OC.sub.2 H.sub.5 N C.sub.2 H.sub.5 OC.sub.2 H.sub.5 NNHCH.sub.3 OC.sub.2 H.sub.5 N NHCH.sub.3 OC.sub.2 H.sub.5 NN(CH.sub.3).sub.2 OC.sub.2 H.sub.5 N N(CH.sub.3).sub.2 OC.sub.2 H.sub.5 NNHCH.sub.3 OCH.sub.2 CF.sub.3 N NHCH.sub.3 OCH.sub.2 CF.sub.3 NN(CH.sub.3).sub.2 OCH.sub.2 CF.sub.3 N N(CH.sub.3).sub.2 OCH.sub.2 CF.sub.3 NCH.sub.3 OC.sub.2 H.sub.5 N CH.sub.3 OC.sub.2 H.sub.5 NCF.sub.3 OCH.sub.3 N CF.sub.3 OCH.sub.3 NOCF.sub.2 H OCH.sub.3 N OCF.sub.2 H OCH.sub.3 NCH.sub.3 OCH.sub.2 CHCH.sub.2 N CH.sub.3 OCH.sub.2 CHCH.sub.2 N__________________________________________________________________________R.sup.1 = CH.sub.3, R.sup.3 = H, R.sup.71 = H, R.sup.1 = CH.sub.3, R.sup.3 = H, R.sup.71 = H,R.sup.2 = NO.sub.2 R.sup.2 = S(O)EtR X Y Z R X Y Z__________________________________________________________________________H CH.sub.3 CH.sub.3 CH H CH.sub.3 CH.sub.3 CHH CH.sub.3 OCH.sub.3 CH H CH.sub.3 OCH.sub.3 CHH OCH.sub.3 OCH.sub.3 CH H OCH.sub.3 OCH.sub.3 CHH Cl OCH.sub.3 CH H Cl OCH.sub.3 CHCH.sub.3 OCH.sub.3 OCH.sub.3 CH CH.sub.3 OCH.sub.3 OCH.sub.3 CHH CH.sub.3 OCH.sub.3 N H CH.sub.3 OCH.sub.3 NH OCH.sub.3 OCH.sub.3 N H OCH.sub.3 OCH.sub.3 NH NHCH.sub.3 OC.sub.2 H.sub.5 N N NHCH.sub.3 OC.sub.2 H.sub.5 NH N(CH.sub.3).sub.2 OC.sub.2 H.sub.5 N H N(CH.sub.3).sub.2 OC.sub.2 H.sub.5 NCH.sub.3 OCH.sub.3 OCH.sub.3 N CH.sub.3 OCH.sub.3 OCH.sub.3 N__________________________________________________________________________R.sup.1 = CH.sub.3, R.sup.3 = H, R.sup.71 = H, R.sup.1 = CH.sub.3, R.sup.3 = H, R.sup.71 = H,R.sup.2 = CHO R.sup.2 = C(O)N(CH.sub.3).sub.2R X Y Z R X Y Z__________________________________________________________________________H CH.sub.3 CH.sub.3 CH H CH.sub.3 CH.sub.3 CHH CH.sub.3 OCH.sub.3 CH H CH.sub.3 OCH.sub.3 CHH OCH.sub.3 OCH.sub.3 CH H OCH.sub.3 OCH.sub.3 CHH Cl OCH.sub.3 CH H Cl OCH.sub.3 CHCH.sub.3 OCH.sub.3 OCH.sub.3 CH CH.sub.3 OCH.sub.3 OCH.sub.3 CHH CH.sub.3 OCH.sub.3 N H CH.sub.3 OCH.sub.3 NH OCH.sub.3 OCH.sub.3 N H OCH.sub.3 OCH.sub.3 NH NHCH.sub.3 OC.sub.2 H.sub.5 N N NHCH.sub.3 OC.sub.2 H.sub.5 NH N(CH.sub.3).sub.2 OC.sub.2 H.sub.5 N H N(CH.sub.3).sub.2 OC.sub.2 H.sub.5 NCH.sub.3 OCH.sub.3 OCH.sub.3 N CH.sub.3 OCH.sub.3 OCH.sub.3 N__________________________________________________________________________R.sup.1 = CH.sub.3, R.sup.3 = H, R.sup.71 = H, R.sup.1 = CH.sub.3, R.sup.3 = H, R.sup.71 = H,R.sup.2 = Cl R.sup.2 = CH.sub.2 OCH.sub.3R X Y Z R X Y Z__________________________________________________________________________H CH.sub.3 CH.sub.3 CH H CH.sub.3 CH.sub.3 CHH CH.sub.3 OCH.sub.3 CH H CH.sub.3 OCH.sub.3 CHH OCH.sub.3 OCH.sub.3 CH H OCH.sub.3 OCH.sub.3 CHH Cl OCH.sub.3 CH H Cl OCH.sub.3 CHCH.sub.3 OCH.sub.3 OCH.sub.3 CH CH.sub.3 OCH.sub.3 OCH.sub.3 CHH CH.sub.3 OCH.sub.3 N H CH.sub.3 OCH.sub.3 NH OCH.sub.3 OCH.sub.3 N H OCH.sub.3 OCH.sub.3 NH NHCH.sub.3 OC.sub.2 H.sub.5 N N NHCH.sub.3 OC.sub.2 H.sub.5 NH N(CH.sub.3).sub.2 OC.sub.2 H.sub.5 N H N(CH.sub.3).sub.2 OC.sub.2 H.sub.5 NCH.sub.3 OCH.sub.3 OCH.sub.3 N CH.sub.3 OCH.sub.3 OCH.sub.3 N__________________________________________________________________________R.sup.1 = CH.sub.3, R.sup.3 = H, R.sup.71 = H, R.sup.1 = CH.sub.3, R.sup.3 = H, R.sup.71 = H,R.sup.2 = SC.sub.2 H.sub.5 R.sup.2 = CHF.sub.2R X Y Z R X Y Z__________________________________________________________________________H CH.sub.3 CH.sub.3 CH H CH.sub.3 CH.sub.3 CHH CH.sub.3 OCH.sub.3 CH H CH.sub.3 OCH.sub.3 CHH OCH.sub.3 OCH.sub.3 CH H OCH.sub.3 OCH.sub.3 CHH Cl OCH.sub.3 CH H Cl OCH.sub.3 CHCH.sub.3 OCH.sub.3 OCH.sub.3 CH CH.sub.3 OCH.sub.3 OCH.sub.3 CHH CH.sub.3 OCH.sub.3 N H CH.sub.3 OCH.sub.3 NH OCH.sub.3 OCH.sub.3 N H OCH.sub.3 OCH.sub.3 NH NHCH.sub.3 OC.sub.2 H.sub.5 N N NHCH.sub.3 OC.sub.2 H.sub.5 NH N(CH.sub.3).sub.2 OC.sub.2 H.sub.5 N H N(CH.sub.3).sub.2 OC.sub.2 H.sub.5 NCH.sub.3 OCH.sub.3 OCH.sub.3 N CH.sub.3 OCH.sub.3 OCH.sub.3 N__________________________________________________________________________R.sup.1 = C.sub.2 H.sub.5 R.sup.3 = R.sup.71 = H, R.sup.1 = CH.sub.3, R.sup.3 = R.sup.71 = H,R.sup.2 = OCH.sub.3 R.sup.2 = OC(O)CH.sub.3R X Y Z R X Y Z__________________________________________________________________________H CH.sub.3 CH.sub.3 CH H CH.sub.3 CH.sub.3 CHH CH.sub.3 OCH.sub.3 CH H CH.sub.3 OCH.sub.3 CHH OCH.sub.3 OCH.sub.3 CH H OCH.sub.3 OCH.sub.3 CHH Cl OCH.sub.3 CH H Cl OCH.sub.3 CHCH.sub.3 OCH.sub.3 OCH.sub.3 CH CH.sub.3 OCH.sub.3 OCH.sub.3 CHH CH.sub.3 OCH.sub.3 N H CH.sub.3 OCH.sub.3 NH OCH.sub.3 OCH.sub.3 N H OCH.sub.3 OCH.sub.3 NH NHCH.sub.3 OC.sub.2 H.sub.5 N N NHCH.sub.3 OC.sub.2 H.sub.5 NH N(CH.sub.3).sub.2 OC.sub.2 H.sub.5 N H N(CH.sub.3).sub.2 OC.sub.2 H.sub.5 NCH.sub.3 OCH.sub.3 OCH.sub.3 N CH.sub.3 OCH.sub.3 OCH.sub.3 N__________________________________________________________________________R.sup.1 = CH.sub.3, R.sup.3 = R.sup.71 = H, R.sup.1 = CH.sub.3, R.sup.3 = R.sup.71 = H,R.sup.2 = OSO.sub.2 CH.sub.3 R.sup.2 = OiPrR X Y Z R X Y Z__________________________________________________________________________H CH.sub.3 CH.sub.3 CH H CH.sub.3 CH.sub.3 CHH CH.sub.3 OCH.sub.3 CH H CH.sub.3 OCH.sub.3 CHH OCH.sub.3 OCH.sub.3 CH H OCH.sub.3 OCH.sub.3 CHH Cl OCH.sub.3 CH H Cl OCH.sub.3 CHCH.sub.3 OCH.sub.3 OCH.sub.3 CH CH.sub.3 OCH.sub.3 OCH.sub.3 CHH CH.sub.3 OCH.sub.3 N H CH.sub.3 OCH.sub.3 NH OCH.sub.3 OCH.sub.3 N H OCH.sub.3 OCH.sub.3 NH NHCH.sub.3 OC.sub.2 H.sub.5 N N NHCH.sub.3 OC.sub.2 H.sub.5 NH N(CH.sub.3).sub.2 OC.sub.2 H.sub.5 N H N(CH.sub.3).sub.2 OC.sub.2 H.sub.5 NCH.sub.3 OCH.sub.3 OCH.sub.3 N CH.sub.3 OCH.sub.3 OCH.sub.3 N__________________________________________________________________________X = Y = OCH.sub.3, Z = CH, R = H,R.sup.71 = HR.sup.1 R.sup.2 R.sup.3__________________________________________________________________________CH.sub.3 CO.sub.2 Et FCH.sub.3 CO.sub.2 Et CH.sub.3CH.sub.2 OCH.sub.3 SO.sub.2 Et ClCH.sub.3 CH.sub.2 CH.sub.2 C(O)CH.sub.3 HEt CO.sub.2 CH.sub.2 OCH.sub.3 HCH.sub.2 CH.sub.2 F NO.sub.2 HCH.sub.2 CH.sub.2 OCH.sub.3 SO.sub.2 NHEt HEt CH(OCH.sub.3).sub.2 BrCH.sub.3 C(O)-n-Pr FCH.sub.3 CH.sub.2 C(O)CH.sub.3 HCH.sub.3 CN HCH.sub.2 OCH.sub.3 CN H__________________________________________________________________________
TABLE 4______________________________________ ##STR63##R = H, R.sup.1 = CH.sub.3, R.sup.3 = R.sup.4 = H,R.sup.2 = CO.sub.2 CH.sub.3, R.sup.71 = HJ A X.sup.1 Y.sup.1 Y.sup.3______________________________________J-1 A-2 CH.sub.3 O --J-1 A-2 OEt O --J-2 A-2 OCH.sub.3 O --J-2 A-2 OCH.sub.3 CH.sub.2 --J-1 A-3 CH.sub.3 -- --J-3 A-3 CH.sub.3 -- --______________________________________R = H, R.sup.1 = CH.sub.3, R.sup.3 = R.sup.4 = H,R.sup.2 = CO.sub.2 CH.sub.3, R.sup.71 = HJ A X.sup.1 Y.sup.1 Y.sup.3______________________________________J-1 A-4 CH.sub.3 -- CH.sub.3J-2 A-4 OCH.sub.3 -- CH.sub.3______________________________________J A X.sup.2 Y.sup.2 X.sup.3______________________________________J-1 A-5 CH.sub.3 CH.sub.3 --J-1 A-6 -- -- OCH.sub.3J-2 A-5 CH.sub.3 SCH.sub.3 --J-2 A-6 -- -- CH.sub.3J-3 A-5 CH.sub.3 OCH.sub.3 --J-3 A-5 CH.sub.2 CF.sub.3 OCH.sub.3 --______________________________________J A X.sup.4 Y.sup.4 Z.sup.1______________________________________J-1 A-7 CH.sub.3 CH.sub.3 CHJ-1 A-7 OCH.sub.3 CH.sub.3 CHJ-2 A-7 OCH.sub.3 OCH.sub.3 NJ-2 A-7 CH.sub.3 OC.sub.2 H.sub.5 CHJ-3 A-7 Cl CH.sub.3 CHJ-3 A-7 CH.sub.3 CH.sub.3 N______________________________________
TABLE 5______________________________________ ##STR64##R.sup.3 = R.sup.4 = H, R.sup.1 = CH.sub.3, R.sup.71 = HJ R.sup.2 Z X______________________________________J-1 CO.sub.2 CH.sub.3 CH OCH.sub.3J-1 CO.sub.2 CH.sub.3 N CH.sub.3J-1 SO.sub.2 N(CH.sub.3).sub.2 CH OCH.sub.3J-1 SO.sub.2 CH.sub.3 N CH.sub.3J-2 CO.sub.2 CH.sub.3 CH ClJ-2 CO.sub.2 CH.sub.3 CH OCH.sub.3J-2 SO.sub.2 N(CH.sub.3).sub.2 N CH.sub.3J-2 CHO N OCH.sub.3J-2 CO.sub.2 CH.sub.3 CH OCH.sub.3J-3 CO.sub.2 CH.sub.3 CH CH.sub.3J-3 SO.sub.2 N(CH.sub.3).sub.2 N CH.sub.3J-3 C(O)CH.sub.3 N OCH.sub.3______________________________________
The procedures of Examples 1 through 18 and Equations 1 through 21 were followed in the synthesis of the following compounds.
INDEX TABLE__________________________________________________________________________ ##STR65##CMPD R.sup.2 X Y Z m.p. (.degree.C.)__________________________________________________________________________J is J-2, R.sup.1 is CH.sub.3, R.sup.4 and R.sup.71 are H 1 CO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 CH 188-190 2 CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 CH 186-188 3 CO.sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 CH 182.5-186.5 4 CO.sub.2 CH.sub.3 Cl OCH.sub.3 CH 186-188.5 5 CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 N 189-190 6 CO.sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 N 182-183 7 CO.sub.2 CH.sub.3 NHCH.sub.3 OEt N 173-179 8 CO.sub.2 CH.sub.3 OEt OEt N 179-180.5 9 SCH.sub.3 CH.sub.3 CH.sub.3 CH 140-154 10 SCH.sub.3 CH.sub.3 OCH.sub.3 CH 176-178 11 SCH.sub.3 OCH.sub.3 OCH.sub.3 CH 181-183 12 SCH.sub.3 Cl OCH.sub.3 CH 165-167 13 SCH.sub.3 CH.sub.3 OCH.sub.3 N 180-183 14 SCH.sub.3 OCH.sub.3 OCH.sub.3 N 174-176 15 SCH.sub.3 NHCH.sub.3 OEt N 124-126 16 SCH.sub.3 NHCH.sub.3 OCH.sub.2 CF.sub.3 N 165-169 17 SCH.sub.3 N(CH.sub.3).sub.2 OCH.sub.2 CF.sub.3 N 116-125 18 SCH.sub.3 Et OEt N 120-123 19 SCH.sub.3 Et OCH.sub.3 N 129-130.5 20 Br CH.sub.3 OCH.sub.3 CH 172-177.5 21 Br OCH.sub.3 OCH.sub.3 CH 149-151.5 22 Br Cl OCH.sub.3 CH 168-175.5 23 Br OCH.sub.3 OCH.sub.3 N 185-188 24 Br OCH.sub.3 OCH.sub.3 H 180-186 25 SO.sub.2 N(CH.sub.3).sub.2 CH.sub.3 CH.sub.3 CH 200-205 26 SO.sub.2 N(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 CH 211-216 27 SO.sub.2 N(CH.sub.3).sub.2 OCH.sub.3 OCH.sub.3 CH 175.5-181 28 SO.sub.2 N(CH.sub.3).sub.2 Cl OCH.sub.3 CH 169-172 29 SO.sub.2 N(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 N 184-190 30 SO.sub.2 N(CH.sub.3).sub.2 OCH.sub.3 OCH.sub.3 N 176.5-178.5 31 SO.sub.2 N(CH.sub.3).sub.2 NHCH.sub.3 OEt N 128-132 32 SO.sub.2 N(CH.sub.3).sub.2 NHCH.sub.3 OCH.sub.2 CF.sub.3 N 144-146 33 SO.sub.2 N(CH.sub.3).sub.2 N(CH.sub.3).sub.2 OCH.sub.2 CF.sub.3 N 143-145 34 SO.sub.2 N(CH.sub.3).sub.2 N(CH.sub.3).sub.2 OCH.sub.3 N 189-191 35 SO.sub.2 N(CH.sub.3).sub.2 Et OEt N 138-140 36 SO.sub.2 N(CH.sub.3).sub.2 Et OCH.sub.3 N 159-160.5 37 C(H)NOCH.sub.3 CH.sub.3 CH.sub.3 CH 193-196 38 C(H)NOCH.sub.3 CH.sub.3 OCH.sub.3 CH 195-197 39 C(H)NOCH.sub.3 OCH.sub.3 OCH.sub.3 CH 172-174 40 C(H)NOCH.sub.3 Cl OCH.sub.3 CH 166-168 41 C(H)NOCH.sub.3 CH.sub.3 OCH.sub.3 N 168-170.5 42 C(H)NOCH.sub.3 OCH.sub.3 OCH.sub.3 N 187-189 43 C(H)NOCH.sub.3 NHCH.sub.3 OEt N 193-195 44 C(H)NOCH.sub.3 OEt OEt N 189-192 45 C(H)NOCH.sub.3 NHCH.sub.3 OCH.sub.2 CF.sub.3 N 119-122 46 C(H)NOCH.sub.3 N(CH.sub.3).sub.2 OCH.sub.2 CF.sub.3 N 158-160 47 C(H)NOCH.sub.3 N(CH.sub.3).sub.2 OCH.sub.3 N 173-176 48 C(H)NOCH.sub.3 Et OEt N 155-156.5 49 C(H)NOCH.sub.3 Et OCH.sub.3 N 137.5-145__________________________________________________________________________CMPD R.sup.1 R.sup.2 R.sup.71 X Y Z m.p. (.degree.C.)__________________________________________________________________________J is J-1, R.sup.3 is H 50 CH.sub.3 CO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH 192-193 51 CH.sub.3 CO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 N 189-190 52 CH.sub.3 CO.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 CH 120-122 53 CH.sub.3 CO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH 112-114 54 CH.sub.3 CO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 N 185-187 55 CH.sub.3 CO.sub.2 CH.sub.3 H Cl OCH.sub.3 CH 209-210 56 CH.sub.3 CO.sub.2 Et H CH.sub.3 CH.sub.3 CH 210-211 57 CH.sub.3 CO.sub.2 Et H CH.sub.3 OCH.sub.3 CH 197-198 58 CH.sub.3 CO.sub.2 Et H OCH.sub.3 OCH.sub.3 CH 176-179 59 CH.sub.3 CO.sub.2 Et H CH.sub.3 OCH.sub.3 N 179-180 60 CH.sub.3 CO.sub.2 Et H OCH.sub.3 OCH.sub.3 N 175-176 61 CH.sub.3 CO.sub.2 Et H Cl OCH.sub.3 CH 192-194 62 CH.sub.3 SO.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 CH 209-120 63 CH.sub.3 SO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH 209-210 64 CH.sub.3 SO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH 197-198 65 CH.sub.3 SO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 N 192-193 66 CH.sub.3 SO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 N 194-195 67 CH.sub.3 SO.sub.2 CH.sub.3 H Cl OCH.sub.3 CH 212-214 68 CH.sub.3 Cl H CH.sub.3 OCH.sub.3 CH 187-188 69 CH.sub.3 Cl H OCH.sub.3 OCH.sub.3 CH 180-183 70 CH.sub.3 Cl H CH.sub.3 OCH.sub.3 N 167-168 71 CH.sub.3 Cl H OCH.sub.3 OCH.sub.3 N 181-182 72 CH.sub.3 Cl H Cl OCH.sub.3 CH 190-192 73 CH.sub.3 SCH.sub.3 H CH.sub.3 OCH.sub.3 CH 181-183 74 CH.sub.3 SCH.sub.3 H OCH.sub.3 OCH.sub.3 CH 178-179 75 CH.sub.3 SCH.sub.3 H CH.sub.3 OCH.sub.3 N 173-174 76 CH.sub.3 SCH.sub.3 H CH.sub.3 OCH.sub.3 N 182-184 77 CH.sub.3 S(O)CH.sub.3 H CH.sub.3 OCH.sub.3 CH 134-135 78 CH.sub.3 S(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH 150d 79 CH.sub.3 S(O)CH.sub.3 H CH.sub.3 OCH.sub.3 N 176d 80 CH.sub.3 S(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 N 129d 81 CH.sub.3 SO.sub.2 Et H CH.sub.3 CH.sub.3 CH 206-209 82 CH.sub.3 SO.sub.2 Et H CH.sub.3 OCH.sub.3 CH 176-179 83 CH.sub.3 SO.sub.2 Et H OCH.sub.3 OCH.sub.3 CH 157-164 84 CH.sub.3 SO.sub.2 Et H CH.sub.3 OCH.sub.3 N 180-182 85 CH.sub.3 SO.sub.2 Et H OCH.sub.3 OCH.sub.3 N 178-182 86 CH.sub.3 SO.sub.2 Et H Cl OCH.sub.3 CH 205-207 87 CH.sub.3 SO.sub.2 n-Pr H CH.sub.3 CH.sub.3 CH 198-200 88 CH.sub.3 SO.sub.2 n-Pr H CH.sub.3 OCH.sub.3 CH 192-194 89 CH.sub.3 SO.sub.2 n-pr H OCH.sub.3 OCH.sub.3 CH 196-199 90 CH.sub.3 SO.sub.2 n-Pr H CH.sub.3 OCH.sub.3 N 190-192 91 CH.sub.3 SO.sub.2 n-Pr H OCH.sub.3 OCH.sub.3 N 179-183 92 CH.sub.3 SO.sub.2 n-pr H Cl OCH.sub.3 CH 201-203 93 CH.sub.3 SEt H CH.sub.3 OCH.sub.3 CH 164-165 94 CH.sub.3 SEt H OCH.sub.3 OCH.sub.3 CH 161-166 95 CH.sub.3 SEt H CH.sub.3 OCH.sub.3 N 161-162 96 CH.sub.3 SEt H OCH.sub.3 OCH.sub.3 N 169-171 97 CH.sub.3 S(n-Pr) H CH.sub.3 OCH.sub.3 CH 149-150 98 CH.sub.3 S(n-Pr) H OCH.sub.3 OCH.sub.3 CH 159-160 99 CH.sub.3 S(n-Pr) H CH.sub.3 OCH.sub.3 N 154-155100 CH.sub.3 S(n-Pr) H OCH.sub.3 OCH.sub.3 N 151-153101 CH.sub.3 C(O)N(CH.sub.3).sub.2 H CH.sub.3 CH.sub.3 CH 181-186102 CH.sub.3 C(O)N(CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 CH 160-162103 CH.sub.3 C(O)N(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH 192-194104 CH.sub.3 C(O)N(CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 N 167-169105 CH.sub.3 C(O)N(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 N 186-187106 CH.sub.3 C(O)N(CH.sub.3).sub.2 H Cl OCH.sub.3 CH 178-181107 Et CO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 N 175-176108 Et CO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 N 173-174109 Et CO.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 CH 212-213110 Et CO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH 190-191111 Et CO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH 178-180112 Et CO.sub.2 CH.sub.3 H Cl OCH.sub.3 CH 194-196113 CH.sub.3 CO.sub.2 iPr H CH.sub.3 CH.sub.3 CH 199-200114 CH.sub.3 CO.sub.2 iPr H CH.sub.3 OCH.sub.3 CH 203-204115 CH.sub.3 CO.sub.2 iPr H OCH.sub.3 OCH.sub.3 CH 194-195116 CH.sub.3 CO.sub.2 iPr H CH.sub.3 OCH.sub.3 N 183-184117 CH.sub.3 CO.sub.2 iPr H OCH.sub.3 OCH.sub.3 N 186-187118 CH.sub.3 CO.sub.2 iPr H Cl OCH.sub.3 CH 200-202119 CH.sub.2 OCH.sub.3 CO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH 166-167120 CH.sub.2 OCH.sub.3 CO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH 145-146121 CH.sub.2 OCH.sub.3 CO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 N 165-166122 CH.sub.2 OCH.sub.3 CO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 N 165-166123 CH.sub.3 CO.sub.2 CH.sub.3 Cl CH.sub.3 CH.sub.3 CH 200-201124 CH.sub.3 CO.sub.2 CH.sub.3 Cl CH.sub.3 OCH.sub.3 CH 194-195125 CH.sub.3 CO.sub.2 CH.sub.3 Cl OCH.sub.3 OCH.sub.3 CH 182-183126 CH.sub.3 CO.sub.2 CH.sub.3 Cl CH.sub.3 OCH.sub.3 N 188-189127 CH.sub.3 CO.sub.2 CH.sub.3 Cl OCH.sub.3 OCH.sub.3 N 188-189128 CH.sub.3 CO.sub.2 CH.sub.3 Cl Cl OCH.sub.3 CH 185-186129 CH.sub.3 CO.sub.2 Et Cl CH.sub.3 CH.sub.3 CH 193-194130 CH.sub.3 CO.sub.2 Et Cl CH.sub.3 OCH.sub.3 CH 191-192131 CH.sub.3 CO.sub.2 Et Cl OCH.sub.3 OCH.sub.3 CH 159-161132 CH.sub.3 CO.sub.2 Et Cl CH.sub.3 OCH.sub.3 N 166-167133 CH.sub.3 CO.sub.2 Et Cl OCH.sub.3 OCH.sub.3 N 167-169134 CH.sub.3 CO.sub.2 Et Cl Cl OCH.sub.3 CH 175-177135 CH.sub.3 CO.sub.2 Et H NHCH.sub.3 OCH.sub.2 CH.sub.3 N 183-185136 CH.sub.3 CO.sub.2 Et H N(CH.sub.3).sub.2 OCH.sub.2 CF.sub.3 N 189-191137 CH.sub.3 CO.sub.2 Et H N(CH.sub.3).sub.2 OEt N 171-173138 Et CO.sub.2 CH.sub.3 H NHCH.sub.3 OEt N 193-195139 Et CO.sub.2 CH.sub.3 H N(CH.sub.3).sub.2 OCH.sub.2 CF.sub.3 N 196-197140 Et CO.sub.2 CH.sub.3 H N(CH.sub.3).sub.2 OEt N 175-177141 Et SO.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 CH 212-213142 Et SO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH 184-185143 Et SO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH 195-196144 Et SO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 N 201-202145 Et SO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 N 186-187146 Et SO.sub.2 CH.sub.3 H Cl OCH.sub.3 CH 204-205147 Et SO.sub.2 Et H CH.sub.3 CH.sub.3 CH 214-215148 Et SO.sub.2 Et H CH.sub.3 OCH.sub.3 CH 196-197149 Et SO.sub.2 Et H OCH.sub.3 OCH.sub.3 CH 205-206150 Et SO.sub.2 Et H CH.sub.3 OCH.sub.3 N 191-192151 Et SO.sub.2 Et H OCH.sub.3 OCH.sub.3 N 191-192152 Et SO.sub.2 Et H Cl OCH.sub.3 CH 189-197153 Et CO.sub.2 Et H CH.sub.3 CH.sub.3 CH 209-210154 Et CO.sub.2 Et H CH.sub.3 OCH.sub.3 CH 161-162155 Et CO.sub.2 Et H OCH.sub.3 OCH.sub.3 CH 160-161156 Et CO.sub.2 Et H CH.sub.3 OCH.sub.3 N 185-186157 Et CO.sub.2 Et H OCH.sub.3 OCH.sub.3 N 166-167158 Et CO.sub.2 Et H Cl OCH.sub.3 CH 166-167159 Et C(O)N(CH.sub.3).sub.2 H CH.sub.3 CH.sub.3 CH 169-171160 Et C(O)N(CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 CH 150-159161 Et C(O)N(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH 192-194162 Et C(O)N(CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 N 174-175163 Et C(O)N(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 N 176-178164 Et C(O)N(CH.sub.3).sub.2 H Cl OCH.sub.3 CH 197-198__________________________________________________________________________CMPD R.sup.1 R.sup.2 R.sup.4 X Y Z m.p. (.degree.C.)__________________________________________________________________________J is J-3, R.sup.71 is H165 CH.sub.3 Br H CH.sub.3 CH.sub.3 CH 197-199166 CH.sub.3 Br H CH.sub.3 OCH.sub.3 CH 206-208167 CH.sub.3 Br H OCH.sub.3 OCH.sub.3 CH 203-205168 CH.sub.3 Br H Cl OCH.sub.3 CH 180-183169 CH.sub.3 Br H CH.sub.3 OCH.sub.3 N 168-173170 CH.sub.3 Br H OCH.sub.3 OCH.sub.3 N 200-202171 CH.sub.3 Br H NHCH.sub.3 OEt N 214-217172 CH.sub.3 CO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH 239-240.5173 CH.sub.3 CO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH 245-248174 CH.sub.3 CO.sub.2 CH.sub.3 H Cl OCH.sub.3 CH 232-234175 CH.sub.3 CO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 N 152-156176 CH.sub.3 CO.sub.2 CH.sub.3 H NHCH.sub.3 OEt N 240-242177 CH.sub.3 CO.sub.2 CH.sub.3 H N(CH.sub.3).sub.2 OEt N 197-199178 CH.sub.3 CO.sub.2 CH.sub.3 H OEt OEt N 180-182179 CH.sub.3 CO.sub.2 CH.sub.3 H N(CH.sub.3).sub.2 OCH.sub.2 CF.sub.3 N 204-206180 CH.sub.3 CO.sub.2 CH.sub.3 H Et OEt N 181-183181 CH.sub.3 CO.sub.2 CH.sub.3 H Et OCH.sub.3 N 216-218182 CH.sub.3 SO.sub.2 N(CH.sub.3).sub.2 H CH.sub.3 CH.sub.3 CH 223-225183 CH.sub.3 SO.sub.2 N(CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 CH 207-209184 CH.sub.3 SO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH 204-206185 CH.sub.3 SO.sub.2 N(CH.sub.3).sub.2 H Cl OCH.sub.3 CH 206-208186 CH.sub.3 SO.sub.2 N(CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 N 185-187187 CH.sub.3 SO.sub.2 N(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 N 176-178188 CH.sub.3 SO.sub.2 N(CH.sub.3).sub.2 H NHCH.sub.3 OEt N 166-168189 CH.sub.3 SO.sub.2 N(CH.sub.3).sub.2 H N(CH.sub.3).sub.2 OEt N 143-145190 CH.sub.3 SO.sub.2 N(CH.sub.3).sub.2 H OEt OEt N 174-176191 CH.sub.3 SO.sub.2 N(CH.sub.3).sub.2 H N(CH.sub.3).sub.2 OCH.sub.2 CF.sub.3 N 178-180192 CH.sub.3 SO.sub.2 N(CH.sub.3).sub.2 H N(CH.sub.3).sub.2 OCH.sub.3 N 213-215193 CH.sub.3 C(O)N(CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 CH 190-196194 CH.sub.3 C(O)N(CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 CH 170-176195 CH.sub.3 C(O)N(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH 193-197196 CH.sub.3 C(O)N(CH.sub.3).sub.2 H Cl OCH.sub.3 CH 143-145197 CH.sub.3 C(O)N(CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 N 123-125198 CH.sub.3 C(O)N(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 N 139.5-142.5199 CH.sub.3 C(O)N(CH.sub.3).sub.2 H NHCH.sub.3 OEt N 189-196200 CH.sub.3 C(O)N(CH.sub.3).sub.2 H N(CH.sub.3).sub.2 OEt N 154.5-162201 CH.sub.3 C(O)N(CH.sub.3).sub.2 H OEt OEt N 183-185202 CH.sub.3 C(O)N(CH.sub.3).sub.2 H N(CH.sub.3).sub.2 OCH.sub.2 CF.sub.3 N 127-129J is J-2, R.sup.71 is H203 CH.sub.3 SO.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 CH 215-216204 CH.sub.3 SO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH 211-212205 CH.sub.3 SO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH 224-226206 CH.sub.3 SO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 N 206-208207 CH.sub.3 SO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 N 198-201208 CH.sub.3 SO.sub.2 CH.sub.3 H Cl OCH.sub.3 CH 228-230209 CH.sub.3 SO.sub.2 CH.sub.3 H NHCH.sub.3 OEt N 248-249210 CH.sub.3 CO.sub.2 Et H CH.sub.3 CH.sub.3 CH 205-206211 CH.sub.3 CO.sub.2 Et H CH.sub.3 OCH.sub.3 CH 192-194212 CH.sub.3 CO.sub.2 Et H OCH.sub.3 OCH.sub.3 CH 172-175213 CH.sub.3 CO.sub.2 Et H CH.sub.3 OCH.sub.3 N 192-194214 CH.sub.3 CO.sub.2 Et H OCH.sub.3 OCH.sub.3 N 171-173215 CH.sub.3 CO.sub.2 Et H Cl OCH.sub.3 CH 197-198216 CH.sub.3 CO.sub.2 Et H NHCH.sub.3 OEt N 184-187217 CH.sub.3 C(O)CH.sub.3 H CH.sub.3 CH.sub.3 CH 181-183218 CH.sub.3 C(O)CH.sub.3 H CH.sub.3 OCH.sub.3 CH 180-181219 CH.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH 152-156220 CH.sub.3 C(O)CH.sub.3 H CH.sub.3 OCH.sub.3 N 152-156221 CH.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 N 184-186222 CH.sub.3 C(O)CH.sub.3 H Cl OCH.sub.3 CH 180-182223 CH.sub.3 C(CH.sub.3)NOCH.sub.3 H CH.sub.3 COH.sub.3 CH 160-163224 CH.sub.3 C(CH.sub.3)NOCH.sub.3 H OCH.sub.3 OCH.sub.3 CH 206-209225 CH.sub.3 C(CH.sub.3)NOCH.sub.3 H CH.sub.3 OCH.sub.3 N 168-170226 CH.sub.3 C(CH.sub.3)NOCH.sub.3 H OCH.sub.3 OCH.sub.3 N 90-113227 CH.sub.3 C(CH.sub.3)NOCH.sub.3 H Cl OCH.sub.3 CH 179-182228 Et CO.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 CH 204-206229 Et CO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH 189-191230 Et CO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH 178-180231 Et CO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 N 175-177232 Et CO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 N 173-176233 Et CO.sub.2 CH.sub.3 H Cl OCH.sub.3 CH 198-200234 Et C(O)N(CH.sub.3).sub.2 H CH.sub.3 CH.sub.3 CH 174-186235 Et C(O)N(CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 CH 134-136236 Et C(O)N(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH 170-176237 Et C(O)N(CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 N 168-170238 Et C(O)N(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 N 147-149239 Et C(O)N(CH.sub.3).sub.2 H Cl OCH.sub.3 CH 116-117240 Et SO.sub.2 Et H CH.sub.3 CH.sub.3 CH 204-205241 Et SO.sub.2 Et H CH.sub.3 OCH.sub.3 CH 200-201242 CH.sub.3 SO.sub.2 Et H OCH.sub.3 OCH.sub.3 CH 199-208243 CH.sub.3 SO.sub.2 Et H CH.sub.3 OCH.sub.3 N 194-195244 CH.sub.3 SO.sub.2 Et H OCH.sub.3 OCH.sub.3 N 189-190245 CH.sub.3 SO.sub.2 Et H Cl OCH.sub.3 CH 200-202246 CH.sub.3 SEt H CH.sub.3 CH.sub.3 CH 178-179247 CH.sub.3 SEt H OCH.sub.3 OCH.sub.3 CH 164-169248 CH.sub.3 SEt H CH.sub.3 OCH.sub.3 N 168-170249 CH.sub.3 SEt H OCH.sub.3 OCH.sub.3 N 175-177250 CH.sub.3 CO.sub.2 iPr H CH.sub.3 CH.sub.3 CH 212-213251 CH.sub.3 CO.sub.2 iPr H CH.sub.3 OCH.sub.3 CH 188-194252 CH.sub.3 CO.sub.2 iPr H OCH.sub.3 OCH.sub.3 CH 158-162253 CH.sub.3 CO.sub.2 iPr H CH.sub.3 OCH.sub.3 N 202-205254 CH.sub.3 CO.sub.2 iPr H OCH.sub.3 OCH.sub.3 N 184-185255 CH.sub.3 CO.sub.2 iPr H Cl OCH.sub.3 CH 191-192256 Et SO.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 CH 184-188257 Et SO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH 202-203258 Et SO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH 186-188259 Et SO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 N 175-178250 Et SO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 N 172-176261 Et SO.sub.2 CH.sub.3 H Cl OCH.sub.3 CH 198-201262 Et SCH.sub.3 H OCH3 OCH.sub.3 CH 150-155263 Et SCH.sub.3 H CH.sub.3 OCH.sub.3 N 140-150264 Et CO.sub.2 Et H CH.sub.3 CH.sub.3 CH 179-180265 Et CO.sub.2 Et H CH.sub.3 OCH.sub.3 CH 168-170266 Et CO.sub.2 Et H OCH.sub.3 OCH.sub.3 CH 167-168267 Et CO.sub.2 Et H CH.sub.3 OCH.sub.3 N 158-159268 Et CO.sub.2 Et H OCH.sub.3 OCH.sub.3 N 174-175269 Et CO.sub.2 Et H Cl OCH.sub.3 CH 181-182270 CH.sub.2 OCH.sub.3 SO.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 CH 182-189271 CH.sub.2 OCH.sub.3 SO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH 162-169272 CH.sub.2 OCH.sub.3 SO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH 179-187273 CH.sub.2 OCH.sub.3 SO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 N 167-170274 CH.sub.2 OCH.sub.3 SO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 N 195-198275 CH.sub.2 OCH.sub.3 SO.sub.2 CH.sub.3 H Cl COH.sub.3 CH 187-192276 Et CO.sub.2 CH.sub.3 H NHCH.sub.3 OEt N 188-190277 Et CO.sub.2 CH.sub.3 H N(CH.sub.3).sub.2 OEt N 171-174278 Et CO.sub.2 CH.sub.3 H N(CH.sub.3).sub.2 OCH2CF.sub.3 N 186-188279 CH.sub.3 CO.sub.2 iPr H N(CH.sub.3).sub.2 OCH.sub.2 CF.sub.3 N 167-169280 Et CO.sub.2 Et H NHCH.sub.3 OEt N 162-164281 Et CO.sub.2 Et H N(CH.sub.3).sub.2 OCH.sub.2 CF.sub.3 N 178-180282 CH.sub.3 CO.sub.2 Et H N(CH.sub.3).sub.2 OCH.sub.2 CF.sub.3 N 173-174283 CH.sub.3 CO.sub.2 CH.sub.3 Br CH.sub.3 CH.sub.3 CH 148-150284 CH.sub.3 CO.sub.2 CH.sub.3 Br CH.sub.3 OCH.sub.3 CH 137-140285 CH.sub.3 CO.sub.2 CH.sub.3 Br OCH.sub.3 OCH.sub.3 CH 154-156286 CH.sub.3 CO.sub.2 CH.sub.3 Br CH.sub.3 OCH.sub.3 N 150-151287 CH.sub.3 CO.sub.2 CH.sub.3 Br OCH.sub.3 OCH.sub.3 N 157-160288 CH.sub.3 CO.sub.2 CH.sub.3 Br Cl OCH.sub.3 CH 152-155289 CH.sub.3 CO.sub.2 CH.sub.3 Br N(CH.sub.3).sub.2 OEt N 145-147J is J-3, R.sup.71 is H290 CH.sub.3 SCH.sub.3 H CH.sub.3 COH.sub.3 CH 217-220291 CH.sub.3 SCH.sub.3 H OCH.sub.3 OCH.sub.3 CH 230-235292 CH.sub.3 SCH.sub.3 H CH.sub.3 OCH.sub.3 N 186-189293 CH.sub.3 SCH.sub.3 H Cl OCH.sub.3 CH 188-190294 CH.sub.3 SCH.sub.3 H N(CH.sub.3).sub.2 OEt N 170-174295 CH.sub.3 Ph H CH.sub.3 OCH.sub.3 CH 180-184296 CH.sub.3 Ph H OCH.sub.3 OCH.sub.3 CH 223-226297 CH.sub.3 Ph H CH.sub.3 OCH.sub.3 N 190-195298 CH.sub.3 Ph H Cl OCH.sub.3 CH 219-221299 CH.sub.3 Ph H N(CH.sub.3).sub.2 OEt N 117-120300 CH.sub.3 SCH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 CH 169-171301 CH.sub.3 SCH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 CH 140-145302 CH.sub.3 SCH.sub.3 CO.sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 CH 153-155303 CH.sub.3 SCH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 N 193-195304 CH.sub.3 SCH.sub.3 CO.sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 N 158-160305 CH.sub.3 SCH.sub.3 CO.sub.2 CH.sub.3 Cl OEt N 187-190306 CH.sub.3 SCH.sub.3 CO.sub.2 CH.sub.3 NHCH.sub.3 OEt N 158-160307 CH.sub.3 Ph CO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 CH 126-128308 CH.sub.3 Ph CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 CH 218-221309 CH.sub.3 Ph CO.sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 CH 224-226310 CH.sub.3 Ph CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 N 201-204311 CH.sub.3 Ph CO.sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 N 201-204312 CH.sub.3 Ph CO.sub.2 CH.sub.3 Cl OCH.sub.3 CH 194-196313 CH.sub.3 Ph CO.sub.2 CH.sub.3 NHCH.sub.3 OEt N 135-138314 CH.sub.3 Ph CO.sub.2 CH.sub.3 N(CH.sub.3).sub.2 OEt N 189-193J is J-2, R.sup.71 is H315 Ph CO.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 CH 209-212316 Ph CO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH 212-215317 Ph CO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH 185-188318 Ph CO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 N 165-170319 Ph CO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 N 160-164320 Ph CO.sub.2 CH.sub.3 H Cl OCH.sub.3 CH 215-220321 Ph CO.sub.2 CH.sub.3 H N(CH.sub.3).sub.2 OEt N 154-160322 CH.sub.3 CN H CH.sub.3 CH.sub.3 CH 218-221323 CH.sub.3 CN H CH.sub.3 OCH.sub.3 CH 212-215324 CH.sub.3 CN H OCH.sub.3 OCH.sub.3 CH 201-204325 CH.sub.3 CN H CH.sub.3 OCH.sub.3 N 213-216326 CH.sub.3 CN H OCH.sub.3 OCH.sub.3 N 216-220327 CH.sub.3 CN H Cl OCH.sub.3 CH 219-220328 CH.sub.3 CN H NHCH.sub.3 OEt N 159-161329 CH.sub.3 CN H N(CH.sub.3).sub.2 OEt N 211-215330 Ph SCH.sub.3 H CH.sub.3 CH.sub.3 CH 216-220331 Ph SCH.sub.3 H CH.sub.3 OCH.sub.3 CH 204-206332 Ph SCH.sub.3 H OCH.sub.3 OCH.sub.3 CH 189-191333 Ph SCH.sub.3 H CH.sub.3 OCH.sub.3 N 187-190334 Ph SCH.sub.3 H OCH.sub.3 OCH.sub.3 N 208-211335 Ph SCH.sub.3 H Cl OCH.sub.3 CH 190-193336 Ph SCH.sub.3 H NHCH.sub.3 OEt N 189-191337 Ph SCH.sub.3 H N(CH.sub.3).sub.2 OEt N 185-187J is J-3, R.sup.71 is H338 CH.sub.3 CN CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 CH >260339 CH.sub.3 CN CO.sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 CH 183-185340 CH.sub.3 CN CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 N 180-183341 CH.sub.3 CN CO.sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 N 231-235342 CH.sub.3 CN CO.sub.2 CH.sub.3 Cl OCH.sub.3 CH >255J is J-2, R.sup.71 is H343 Ph SO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH 225-226344 Ph SO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH 212-216345 Ph SO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 N 199-201346 Ph SO.sub.2 CH.sub.3 H OCH.sub.3 Cl CH 209-211J is J-3, R.sup.71 is H347 CH.sub.3 CN CHO CH.sub.3 OCH.sub.3 CH 179-180348 CH.sub.3 CN CHO OCH.sub.3 OCH.sub.3 CH 181-184349 CH.sub.3 CN CHO CH.sub.3 OCH.sub.3 N 229-233350 CH.sub.3 CN CHO Cl COH.sub.3 CH 155-159J is J-2, R.sup.71 is H351 Ph CHO H CH.sub.3 CH.sub.3 CH 149-151352 Ph CHO H CH.sub.3 OCH.sub.3 CH 171-174353 Ph CHO H OCH.sub.3 OCH.sub.3 CH 146-150354 Ph CHO H CH.sub.3 OCH.sub.3 N 160-164355 Ph CHO H OCH.sub.3 OCH.sub.3 N 147-150356 Ph CHO H Cl OCH.sub.3 CH 161-165357 Ph CHO H N(CH.sub.3).sub.2 OEt N 135-137J is J-3, R.sup.71 is H358 CH.sub.3 CN CON(CH.sub.3).sub.2 CH.sub.3 OCH.sub.3 CH 92-95359 CH.sub.3 CN CON(CH.sub.3).sub.2 OCH.sub.3 OCH.sub.3 CH 168-171360 CH.sub.3 CN CON(CH.sub.3).sub.2 CH.sub.3 OCH3 N 120-125361 CH.sub.3 CN CON(CH.sub.3).sub.2 OCH.sub.3 Cl CH 165-170362 CH.sub.3 CN CON(CH.sub.3).sub.2 N(CH.sub.3).sub.2 OEt N 129-131363 CH.sub.3 CO.sub.2 CH.sub.3 SCH.sub.3 CH.sub.3 OCH.sub.3 CH 190-193364 CH.sub.3 CO.sub.2 CH.sub.3 SCH.sub.3 OCH.sub.3 OCH.sub.3 CH 125-127365 CH.sub.3 CO.sub.2 CH.sub.3 SCH.sub.3 CH.sub.3 OCH.sub.3 N 183-185366 CH.sub.3 CO.sub.2 CH.sub.3 SCH.sub.3 Cl OCH.sub.3 CH 168-170367 CH.sub.3 CO.sub.2 CH.sub.3 SCH.sub.3 N(CH.sub.3).sub.2 OEt N 210-215368 H CO.sub.2 CH.sub.3 H CH.sub.3 CH.sub.3 CH 215-217369 H CO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 CH 200-202370 H CO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 CH 218-220371 H CO.sub.2 CH.sub.3 H Cl OCH.sub.3 CH 221-223372 H CO.sub.2 CH.sub.3 H CH.sub.3 OCH.sub.3 N 138-142373 H CO.sub.2 CH.sub.3 H OCH.sub.3 OCH.sub.3 N 230-234374 H CO.sub.2 CH.sub.3 H NHCH.sub.3 OEt N 146-148375 H CO.sub.2 CH.sub.3 H N(CH.sub.3).sub.2 OEt N 185-187376 CH.sub.3 C(O)CH.sub.3 H CH.sub.3 CH.sub.3 CH 247-249377 CH.sub.3 C(O)CH.sub.3 H CH.sub.3 OCH.sub.3 CH 245-247378 CH.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 CH 233-235379 CH.sub.3 C(O)CH.sub.3 H Cl OCH.sub.3 CH 237-239380 CH.sub.3 C(O)CH.sub.3 H CH.sub.3 OCH.sub.3 N 204-206381 CH.sub.3 C(O)CH.sub.3 H OCH.sub.3 OCH.sub.3 N 216-218382 CH.sub.3 C(O)CH.sub.3 H NHCH.sub.3 OEt N 249-252383 CH.sub.3 C(O)CH.sub.3 H N(CH.sub.3).sub.2 OEt N 225-227J is J-2, R.sup.71 is H384 CH.sub.3 C(O)N(CH.sub.3).sub.2 H CH.sub.3 CH.sub.3 CH 159-166385 CH.sub.3 C(O)N(CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 CH 131-136386 CH.sub.3 C(O)N(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 CH 140-147387 CH.sub.3 C(O)N(CH.sub.3).sub.2 H Cl OCH.sub.3 CH 103-107388 CH.sub.3 C(O)N(CH.sub.3).sub.2 H CH.sub.3 OCH.sub.3 N oil389 CH.sub.3 C(O)N(CH.sub.3).sub.2 H OCH.sub.3 OCH.sub.3 N oil390 CH.sub.3 C(O)N(CH.sub.3).sub.2 H NHCH.sub.3 OEt N 140-142391 CH.sub.3 C(O)N(CH.sub.3).sub.2 H N(CH.sub.3).sub.2 OEt N 178-180392 CH.sub.3 C(O)N(CH.sub.3).sub.2 H OEt OEt N 121-125393 CH.sub.3 C(O)N(CH.sub.3).sub.2 H NHCH.sub.3 OCH.sub.2 CF.sub.3 N 155-160394 CH.sub.3 C(O)N(CH.sub.3).sub.2 H N(CH.sub.3).sub.2 OCH.sub.2 CF.sub.3 N 250395 CH.sub.3 C(O)N(CH.sub.3).sub.2 H N(CH.sub.3).sub.2 OCH.sub.3 N gum396 CH.sub.3 C(O)N(CH.sub.3).sub.2 H Et OEt N gum397 CH.sub.3 C(O)N(CH.sub.3).sub.2 H Et OCH.sub.3 N gum398 CH.sub.3 CHO H CH.sub.3 OCH.sub.3 CH 140-141.5399 CH.sub.3 CHO H OCH.sub.3 OCH.sub.3 CH 172-174.5400 CH.sub.3 CHO H Cl OCH.sub.3 CH 172-175401 CH.sub.3 CHO H CH.sub.3 OCH.sub.3 N 156-160402 CH.sub.3 CHO H OCH.sub.3 OCH.sub.3 N 173-177403 CH.sub.3 CHO H NHCH.sub.3 OEt N 176-179404 CH.sub.3 CHO H OEt OEt N 102-104405 CH.sub.3 CHO H Et OEt N 149-151.5406 CH.sub.3 CHO H Et OCH.sub.3 N 148-150__________________________________________________________________________CMPD R.sup.1 R.sup.2 X Y Z m.p. (.degree.C.)__________________________________________________________________________J is J-1, R.sup.3 and R.sup.71 is H407 (CH.sub.2).sub.3 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 CH 188-189408 (CH.sub.2).sub.3 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 CH 138-140409 (CH.sub.2).sub.3 CH.sub.3 CO.sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 CH 139-140410 (CH.sub.2).sub.3 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 OCH.sub.3 N 137-138411 (CH.sub.2).sub.3 CH.sub.3 CO.sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 N 152-155412 (CH.sub.2).sub.3 CH.sub.3 CO.sub.2 CH.sub.3 Cl OCH.sub.3 CH 162-164413 CH.sub.3 OC.sub.2 H.sub.5 CH.sub.3 OCH.sub.3 CH 180-181.degree.d414 CH.sub.3 OC.sub.2 H.sub.5 OCH.sub.3 OCH.sub.3 CH 170-172.degree.d415 CH.sub.3 OC.sub.2 H.sub.5 CH.sub.3 OCH.sub.3 N 178-179.degree.d416 CH.sub.3 OC.sub.2 H.sub.5 OCH.sub.3 OCH.sub.3 N 175-177.degree.d417 CH.sub.3 CN CH.sub.3 CH.sub.3 CH 198-200.degree.d418 CH.sub.3 CN CH.sub.3 OCH.sub.3 CH 178-184.degree.d419 CH.sub.3 CN OCH.sub.3 OCH.sub.3 CH 199-201.degree.d420 CH.sub.3 CN CH.sub.3 OCH.sub.3 N 184-186.degree.d421 CH.sub.3 CN OCH.sub.3 OCH.sub.3 N 180-182.degree.d422 CH.sub.3 CN Cl OCH.sub.3 CH 199-201.degree.d__________________________________________________________________________CMPD R.sup.1 R.sup.2 R.sup.4 X Y Z m.p. (.degree.C.)__________________________________________________________________________J is J-3, R.sup.71 is H423 CH.sub.3 CN CHO OCH.sub.3 CH.sub.3 CH 179-180424 CH.sub.3 CN CHO OCH.sub.3 OCH.sub.3 CH 181-184425 CH.sub.3 CN CHO OCH.sub.3 CH.sub.3 N 229-233426 CH.sub.3 CN CHO OCH.sub.3 Cl CH 155-159427 CH.sub.3 CN C(O)N(CH.sub.3).sub.2 OCH.sub.3 CH.sub.3 CH 92-95428 CH.sub.3 CN C(O)N(CH.sub.3).sub.2 OCH.sub.3 OCH.sub.3 CH 168-171429 CH.sub.3 CN C(O)N(CH.sub.3).sub.2 OCH.sub.3 CH.sub.3 N 120-123430 CH.sub.3 CN C(O)N(CH.sub.3).sub.2 OCH.sub.3 Cl CH 165-170431 CH.sub.3 CN C(O)N(CH.sub.3).sub.2 OEt N(CH.sub.3).sub.2 N 129-131432 CH.sub.3 CO.sub.2 CH.sub.3 SCH.sub.3 OCH.sub.3 CH.sub.3 CH 190-193433 CH.sub.3 CO.sub.2 CH.sub.3 SCH.sub.3 OCH.sub.3 OCH.sub.3 CH 125-127434 CH.sub.3 CO.sub.2 CH.sub.3 SCH.sub.3 OCH.sub.3 CH.sub.3 N 183-185435 CH.sub.3 CO.sub.2 CH.sub.3 SCH.sub.3 OCH.sub.3 Cl CH 168-170436 CH.sub.3 CO.sub.2 CH.sub.3 SCH.sub.3 OEt N(CH.sub.3).sub.2 N 210-215437 CH.sub.3 CN Br CH.sub.3 CH.sub.3 CH 153-156438 CH.sub.3 CN Br OCH.sub.3 CH.sub.3 CH 168-171439 CH.sub.3 CN Br OCH.sub.3 OCH.sub.3 CH 150-153440 CH.sub.3 CN Br OCH.sub.3 CH.sub.3 N 159-162441 CH.sub.3 CN Br OCH.sub.3 OCH.sub.3 N 164-167442 CH.sub.3 CN Br OCH.sub.3 Cl CH >210443 CH.sub.3 CN Br OEt N(CH.sub.3).sub.2 N >210444 CH.sub.3 CH.sub.3 CO.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 CH 205-209445 CH.sub.3 CH.sub.3 CO.sub.2 CH.sub.3 OCH.sub.3 CH.sub.3 CH 196-200446 CH.sub.3 CH.sub.3 CO.sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 CH 186-188447 CH.sub.3 CH.sub.3 CO.sub.2 CH.sub.3 OCH.sub.3 CH.sub.3 N 201-202448 CH.sub.3 CH.sub.3 CO.sub.2 CH.sub.3 OCH.sub.3 OCH.sub.3 N 185-186449 CH.sub.3 CH.sub.3 CO.sub.2 CH.sub.3 OCH.sub.3 Cl CH 175-178450 CH.sub.3 CH.sub.3 CO.sub.2 CH.sub.3 OEt N(CH.sub.3).sub.2 N 154-157.degree.451 CH.sub.3 CN C(O)CH.sub.3 OCH.sub.3 CH.sub.3 CH 159-162452 CH.sub.3 CN C(O)CH.sub.3 OCH.sub.3 OCH.sub.3 CH 175-178453 CH.sub.3 CN C(O)CH.sub.3 OCH.sub.3 CH.sub.3 N 180-182454 CH.sub.3 CN C(O)CH.sub.3 OCH.sub.3 Cl CH >240455 CH.sub.3 CN SO.sub.2 Et OCH.sub.3 CH.sub.3 CH 168-170456 CH.sub.3 CN SO.sub.2 Et OCH.sub.3 OCH.sub.3 CH 161-164457 CH.sub.3 CN SO.sub.2 Et OCH.sub.3 CH.sub.3 N 170-174458 CH.sub.3 CN SO.sub.2 Et OCH.sub.3 Cl CH 195-200459 CH.sub.3 CN SO.sub.2 Et OEt N(CH.sub.3).sub.2 N >200460 CH.sub.3 CO.sub.2 CH.sub.3 Br OCH.sub.3 CH.sub.3 N 192-193461 CH.sub.3 CO.sub.2 CH.sub.3 Br OCH.sub.3 OCH.sub.3 N 193-197462 CH.sub.3 CO.sub.2 CH.sub.3 Br OCH.sub.3 Cl CH 194-195463 CH.sub.3 SO.sub.2 Et H OCH.sub.3 CH.sub.3 CH 172-173464 CH.sub.3 SO.sub.2 Et H OCH.sub.3 OCH.sub.3 CH 183-184465 CH.sub.3 SO.sub.2 Et H CH.sub.3 OCH.sub.3 N 189-190466 CH.sub.3 SO.sub.2 Et H OCH.sub.3 OCH.sub.3 N 193-194__________________________________________________________________________
FORMULATIONS
Useful formulations of the compounds of Formula I can be prepared in conventional ways. They include dusts, granules, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates and the like. Many of these may be applied directly. Sprayable formulations can be extended in suitable media and used at spray volumes of from a few liters to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation. The formulations, broadly, contain about 0.1% to 99% by weight of active ingredient(s) and at least one of (a) about 0.1% to 20% surfactant(s) and (b) about 1% to 99.9% solid or liquid inert diluent(s). More specifically, they will contain these ingredients in the following approximate proportions:
______________________________________ Weight Percent* Active Ingredient Diluent(s) Surfactant(s)______________________________________Wettable Powders 20-90 0-74 1-10Oil Suspensions, 3-50 40-95 0-15Emulsions, Solutions,(including EmulsifiableConcentrates)Aqueous Suspension 10-50 40-84 1-20Dusts 1-25 70-99 0-5Granules and Pellets 0.1-95 5-99.9 1-15High Strength 90-99 0-10 0-2Compositions______________________________________ *Active ingredient plus at least one of a Surfactant or a Diluent equals 100 weight percent.
Lower or higher levels of active ingredient can, of course, be present depending on the intended use and the physical properties of the compound. Higher ratios of surfactant to active ingredient are sometimes desirable, and are achieved by incorporation into the formulation or by tank mixing.
Typical solid diluents are described in Watkins, et al., "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books, Caldwell, N.J., but other solids, either mined or manufactured, may be used. The more absorptive diluents are preferred for wettable powders and the denser ones for dusts. Typical liquid diluents and solvents are described in Marsden, "Solvents Guide," 2nd Ed., Interscience, New York, 1950. Solubility under 0.1% is preferred for suspension concentrates; solution concentrates are preferably stable against phase separation at 0.degree. C. "McCutcheon's Detergents and Emulsifiers Annual", MC Publishing Corp., Ridgewood, N.J., as well as Sisely and Wood, "Encyclopedia of Surface Active Agents", Chemical Publishing Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor mounts of additives to reduce foaming, caking, corrosion, microbiological growth, etc.
The methods of making such compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer or fluid energy mill. Suspensions are prepared by wet milling (see, for example, Littler, U.S. Pat. No. 3,060,084). Granules and pellets may be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See J. E. Browning, "Agglomeration", Chemical Engineering, Dec. 4, 1967, pp. 147ff. and "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York, 1963, pp. 8-57ff.
For further information regarding the art of formulation, see for example:
H. M. Loux, U.S. Pat. No. 3,235,361, Feb. 15, 1966, Col. 6, line 16 through Col. 7, line 19 and Examples 10 through 41;
R. W. Luckenbaugh, U.S. Pat. No. 3,309,192, Mar. 14, 1967, 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;
H. Gysin and E. Knusli, U.S. Pat. No. 2,891,855, Jun. 23, 1959, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4;
G. C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, pp. 81-96; and
J. D. Fryer and S. A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103.
In the following examples, all parts are by weight unless otherwise indicated.
EXAMPLE A
______________________________________High Strength Concentrate______________________________________methyl 3-[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]- 99%carbonyl]amino]sulfonyl]-1-methyl-1H-pyrrole-2-carboxylatetrimethylnonyl polyethylene 1%glycol ether______________________________________
The surfactant is sprayed upon the active ingredient in a blender and the mixture sifted through a U.S.S. No. 40 sieve (0.42 mm openings) prior to packaging. The concentrate may be formulated further for practical use.
EXAMPLE B
______________________________________Wettable Powder______________________________________methyl 3[[[[[4-ethoxy-6-(methylamino)-1,3,5-triazin-2- 65%yl]amino]carbonyl]amino]sulfonyl]-1-methyl-1H-pyrrole-2-carboxylatedodecylphenol polyethylene glycol ether 2%sodium ligninsulfonate 4%sodium silicoaluminate 6%montmorillonite (calcined) 23%______________________________________
The ingredients are thoroughly blended. The liquid surfactant is added by spraying upon the solid ingredients in the blender. After grinding in a hammer mill to produce particles essentially all below 100 microns, the material is reblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) and packaged.
EXAMPLE C
______________________________________Aqueous Suspension______________________________________methyl 3-[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]- 50.0%carbonyl]amino]sulfonyl]-1-methyl-1H-pyrrole-2-carboxylatepolyacrylic acid thickener 0.3%dodecylphenol polyethylene 0.5%glycol etherdisodium phosphate 1%monosodium phosphate 0.5%polyvinyl alcohol 1.0%water 56.7%______________________________________
The ingredients are blended and ground together in a sand mill to produce particles essentially all under 5 microns in size.
EXAMPLE D
______________________________________Oil Suspension______________________________________methyl 3[[[[[4-ethoxy-6-(methylamino)-1,3,5-triazin-2- 35%yl]amino]carbonyl]amino]sulfonyl]-1-methyl-1H-pyrrole-2-carboxylateblend of polyalcohol carboxylic esters 6%and oil soluble petroleum sulfonatesxylene 59%______________________________________
The ingredients are combined and ground together in a sand mill to produce particles essentially all below 3 microns. The product can be used directly, extended with oils, or emulsified in water.
EXAMPLE E
______________________________________Oil Suspension______________________________________methyl 3-[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]- 25%carbonyl]amino]sulfonyl]-1-methyl-1H-pyrrole-2-carboxylatepolyoxyethylene sorbitol hexaoleate 5%highly aliphatic hydrocarbon oil 70%______________________________________
The ingredients are ground together in a sand mill until the solid particles have been reduced to under about 5 microns. The resulting thick suspension may be applied directly, but preferably after being extended with oils or emulsified in water.
EXAMPLE F
______________________________________Aqueous Suspension______________________________________methyl 3[[[[[4-ethoxy-6-(methylamino)-1,3,5-triazine-2- 25%yl]amino]carbonyl]amino]sulfonyl]-1-methyl-1H-pyrrole-2-carboxylatehydrated attapulgite 3%crude calcium ligninsulfonate 10%sodium dihydrogen phosphate 0.5%water 61.5%______________________________________
The ingredients are ground together in a ball or roller mill until the solid particles have been reduced to diameters under 10 microns.
EXAMPLE G
______________________________________Wettable Powder______________________________________methyl 3-[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]- 40.0%carbonyl]amino]sulfonyl]-1-methyl-1H-pyrrole-2-carboxylatedioctyl sodium sulfosuccinate 1.5%sodium ligninsulfonate 3%low viscosity methyl cellulose 1.5%attapulgite 54%______________________________________
The ingredients are thoroughly blended, passed through an air mill, to produce an average particle size under 15 microns, reblended, and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) before packaging.
All compounds of the invention may be formulated in the same manner.
EXAMPLE H
______________________________________Granule______________________________________wettable powder of Example G 15%gypsum 69%potassium sulfate 16%______________________________________
The ingredients are blended in a rotating mixer and water sprayed on to accomplish granulation. When most of the material has reached the desired range of 1.0 to 0.42 cm (U.S.S. #18 to 40 sieves), the granules are removed, dried, and screened. Oversized material is crushed to produce additional material in the desired range. These granules contain % active ingredient.
EXAMPLE I
______________________________________Wettable Powder______________________________________methyl 3[[[[[4-ethoxy-6-(methylamino)-1,3,5-triazin-2- 50%yl]amino]carbonyl]amino]sulfonyl]-1-methyl-1H-pyrrole-2-carboxylatesodium alkylnaphthalenesulfonate 2%low viscosity methyl cellulose 2%diatomaceous earth 46%______________________________________
The ingredients are blended, coarsely hammer-milled and the air milled to produce particles of active essentially all below 10 microns in diameter. The product is reblended before packaging.
EXAMPLE J
______________________________________Extruded Pellet______________________________________methyl 3-[[[[(4,6-diemthoxy-2-pyrimidinyl)amino]- 25%carbonyl]amino]sulfonyl]-1-methyl-1H-pyrrole-2-carboxylateanhydrous sodium sulfate 10%crude calcium ligninsulfonate 5%sodium alkylnaphthalenesulfonate 1%calcium/magnesium bentonite 59%______________________________________
The ingredients are blended, hammer-milled and then moistened with about 12% water. The mixture is extruded as cylinders about 3 mm diameter which are cut to produce pellets about 3 mm long. These may be used directly after drying, or the dried pellets may be crushed to pass a U.S.S. No. 20 sieve (0.84 mm openings). The granules held on a U.S.S. No. 40 sieve (0.42 mm openings) may be packaged for use and the fines recycled.
EXAMPLE K
______________________________________Wettable Powder______________________________________methyl 3[[[[[4-ethoxy-6-(methylamino)-1,3,5-triazin-2- 80%yl]amino]carbonyl]amino]sulfonyl]-1-methyl-1H-pyrrole-2-carboxylatesodium alkylnaphthalenesulfonate 2%sodium ligninsulfonate 2%synthetic amorphous silica 3%kaolinite 13%______________________________________
The ingredients are blended and then ground in a hammer mill to produce particles with an average particle size less than 25 microns in diameter. The material is reblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) before being packaged.
EXAMPLE L
______________________________________High Strength Concentrate______________________________________methyl 3-[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]- 98.5%carbonyl]amino]sulfonyl]-1-methyl-1H-pyrrole-2-carboxylatesilica aerogel 0.5%synthetic amorphous fine silica 1.0%______________________________________
The ingredients are blended and ground in a hammer mill to produce a high strength concentrate essentially all passing a U.S.S. No. 50 sieve (0.3 mm openings). This material may then be formulated in a variety of ways.
EXAMPLE M
______________________________________Solution______________________________________methyl 3[[[[[4-ethoxy-6-(methylamino)-1,3,5-triazin-2-yl]amino]carbonyl]amino]sulfonyl]-1-methyl-1H-pyrrole-2-carboxylatesodium salt 5%water 95%______________________________________
The salt is added directly to the water with stirring to produce the solution, which may then be packaged for use.
EXAMPLE N
______________________________________Solution______________________________________methyl 3-[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]-carbonyl]amino]sulfonyl]-1-methyl-1H-pyrrole-2-carboxylatesodium salt 5%water 95%______________________________________
The salt is added directly to the water with stirring to produce the solution, which may then be packaged for use.
UTILITY
Test results indicate compounds of this invention are active postemergence and preemergence herbicides. Compounds in this invention are useful for the control of selected grass and broadleaf weeds with tolerance to important agronomic crops which include, but are not limited to barley (Hordeum vulgare), cotton (Gossypium hirsutum), rape (Brassica napus), rice (Oryza sativa), and wheat (Triticum aestivum). Grass and broadleaf weed species controlled include, but are not limited to, bedstraw (Galium spp.), brome (Bromus spp.), lambsquarters (Chenopodium spp.), and umbrella sedge (Cyperus spp.). A few compounds in this invention are useful for the control of selected broadleaf weeds such as umbrella sedge in upland and paddy rice.
These compounds also have utility for control of vegetation in specified areas such as around storage tanks, parking lots, highways, and railways; in fallow crop areas; and in citrus and plantation crops such as banana, coffee, oil palm, and rubber. Alternatively, these compounds are useful to modify plant growth or as citrus abscission agents.
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 the subject compounds is applied at rates from 0.001 to 20 kg/ha with a preferred rate range of 0.004 to 0.25 kg/ha. One skilled in the art can easily determine application rates necessary for the desired level of weed control.
Compounds of this invention may be used alone or in combination with other commercial herbicides, insecticides, or fungicides. The following list exemplifies some of the herbicides suitable for use in mixtures. A combination of a compound from this invention with one or more of the following herbicides may be particularly useful for weed control.
______________________________________Common Name Chemical Name______________________________________acetochlor 2-chloro-N-(ethoxymethyl)-N- (2-ethyl,-6-methylphenyl)acetamideacifluorfen 5-[2-chloro-4-(trifluoromethyl)- phenoxy]-2-nitrobenzoic addacrolein 2-propenalalachlor 2-chloro-N-(2,6-diethylphenyl)-N- (methoxymethyl)acetamideanilofos S-4-chloro-N-isopropylcarbaniloyl- methyl-O,O-dimethyl phosphorodi- thioateametryn N-ethyl-N'-(1-methylethyl)-6- (methylthio)-1,3,5-triazine-2,4- diamineamitrole 1H-1,2,4-triazol-3-amineAMS ammonium sulfamateasulam methyl [(4-aminophenyl)sulfonyl]- carbamateatrazine 6-chloro-N-ethyl-N'-(1-methylethyl)- 1,3,5-triazine-2,4-diaminebarban 4-chloro-2-butynyl 3-chlorocarbamatebenefin N-butyl-N-ethyl-2,6-dinitro-4-(tri- fluoromethyl)benzenaminebensulfuron 2-[[[[[(4,6-dimethoxy-2-pyrimi-methyl dinyl)amino]methylcarbonyl]- amino]sulfonyl]methyl]benzoic acid, methyl esterbensulfide O,O-bis(1-methylethyl) S-[2- [(phenylsulfonyl)amino]- ethyl]phosphorodithioatebentazon 3-(1-methylethyl)-(1H)-2,1,3- benzothiadiazin-4(3H)-one, 2,2-dioxidebenzofluor N-[4-(ethylthio)-2-(trifluoro- methyl)phenyl]methanesulfonamidebenzoylprop N-benzoyl-N-(3,4-dichlorophenyl)-DL- alaninebifenox methyl 5-(2,4-dichlorophenoxy)-2- nitrobenzoatebromacil 5-bromo-6-methyl-3-(1-methylpropyl)- 2,4(1H,3H)pyrimidinedionebromoxynil 3,5-dibromo-4-hydroxybenzonitrilebutachlor N-(butoxymethyl)-2-chloro-N-(2,6- diethylphenyl)acetamidebuthidazole 3-[5-(1,1-dimethylethyl)-1,3,4-thia- diazol-2-yl]-4-hydroxy-1-methyl-2- imidazolidinonebutralin 4-(1,1-dimethylethyl)-N-(1-methyl- propyl)-2,6-dinitrobenzenaminebutylate S-ethyl bis(2-methylpropyl)- carbamothioatecacodylic dimethyl arsinic oxideacidCDAA 2-chloro-N,N-di-2-propenylacetamideCDEC 2-chloroallyl diethyldithiocarbamateCGA 142,464 3-(4,6-dimethoxy-1,3,5-triazin-2-yl)- 1-[2-(2-methoxyethoxy)-pehnyl- sulfonyl]-ureachloramben 3-amino-2,5-dichlorobenzoic acidchlorbromuron 3-(4-bromo-3-chlorophenyl)-1-methoxy-1- methylureachlorimuron 2-[[[[(4-chloro-6-methoxy-2-pyrimi-ethyl dinyl)ethylamino]carbonyl]- amino]sulfonyl]benzoic acid, ethyl esterchlormethoxy- 2,4-dichlorophenyl 4-nitro-3-nil methoxyphenyl etherchlornitrofen 2,4,6-trichlorophenyl-4-nitro- phenyl etherchloroxuron N'-[4-(4-chlorophenoxy)phenyl]-N,N- dimethylureachlorpropham 1-methylethyl 3-chlorophenylcarbamatechlorsulfuron 2-chloro-N-[[(4-methoxy-6-methyl-1,3,5- triazin-2-yl)amino]carbonyl]benzene- sulfonamidechlortoluron N'-(3-chloro-4-methylphenyl)-N,N- dimethylureacinmethylin exo-1-methyl-4-(1-methylethyl)-2-[(2- methylphenyl)methoxy]-7-oxabicyclo- [2.2.l]heptaneclethodim (E,E)-(.+-.)-2-[1-[[(3-chloro-2-propenyl)- oxy]iminolpropyl]-5-[2-(ethylthio)- propyl]-3-hydroxy-2-cyclohexen-1-oneclomazone 2-[(2-chlorophenyl)methyl]-4,4-dimethyl- 3-isoxazolidinonecloproxydim (EE)-2-[1-[[(3-chloro-2-propenyl)oxy)- imino]butyl]-5-[2-(ethylthio)propyl]- 3-hydroxy-2-cyclohexen-1-oneclopyralid 3,6-dichloro-2-pyridinecarboxylic acidCMA calcium salt of MAAcyanazine 2-[[4-chloro-6-(ethylamino)-1,3,5-tri- azin-2-yl]amino]-2-methylpropanenitrilecycloate S-ethyl cyclohexylethylcarbamothioatecycluron 3-cyclooctyl-1,1-dimethylureacyperquat 1-methyl-4-phenylpyridiniumcyprazine 2-chloro-4-(cyclopropylamino)-6-(iso- propylamino)-s*-triazinecyprazole N-[5-(2-chloro-1,1-dimethylethyl)-1,3,4- thiadiazol-2-yl]cyclopropanecarbox- amidecypromid 3',4'-dichlorocyclopropanecarboxanilidedalapon 2,2-dichloropropanoic aciddazomet tetrahydro-3,5-dimethyl-2H-1,3,5-thia- diazine-2-thioneDCPA dimethyl 2,3,5,6-tetrachloro-1,4-benzene- dicarboxylatedesmediphan ethyl [3-[[(phenylamino)carbonyl]oxy]- phenyl]carbamatedesmetryn 2-(isopropylamino)-4-(methylamino)-6- (methylthio)-s*-triazinediallate S-(2,3-dichloro-2-propenyl)bis(1- methylethyl)carbamothioatedicamba 3,6-dichloro-2-methoxybenzoic aciddichlobenil 2,6-dichlorobenzonitriledichlorprop (.+-.)-2-(2,4-dichlorophenoxy)propanoic aciddichlofop (.+-.)-2-[4-(2,4-dichlorophenoxy)phenoxy]- propanoic acid, methyl esterdiethatyl N-(chloroacetyl)-N-(2,6-diethylphenyl)- glycinedifenzoquat 1,2-dimethyl-3,5-diphenyl-1H-pyrazoliumdimepiperate S-1-methyl-1-phenylethylpiperidine- 1-carbothioatedinitramine N.sup.3,N.sup.3 -diethyl-2,4-dinitro-6-(trifluoro- methyl)-1,3-benzenediaminedinoseb 2-(1-methylpropyl)-4,6-dinitrophenoldiphenamid N,N-dimethyl-a-phenylbenzeneacetamidedipropetryn 6-(ethylthio)-N,N'-bis(1-methylethyl)- 1,3,5-triazine-2,4-diaminediquat 6,7-dihydrodipyrido[1,2-a:2',1'-c]- pyrazinedium iondiuron N'-(3,4-dichlorophenyl)-N,N-dimethylureaDNOC 2-methyl-4,6-dinitrophenolDSMA disodium salt of MAAdymron N-(4-methylphenyl)-N'-(1-methyl- 1-phenylethyl)ureaendothall 7-oxabicyclo[2.2.1]heptane-2,3-dicarbox- ylic acidEPTC S-ethyl dipropylcarbamothioateesprocarb S-benzyl-N-ethyl-N-(1,2-dimethyl)-(SC2957) propyl)thiolcarbamateethalfluralin N-ethyl-N-(2-methyl-2-propenyl)-2,6- dinitro-4-(trifluoromethyl)- benzenamineethofumesate (.+-.)-2-ethoxy-2,3-dihydro-3,3-dimethyl- 5-benzofuranyl methanesulfonatefenac 2,3,6-trichlorobenzeneacetic acidfenoxaprop (.+-.)-2-[4-[(6-chloro-2-benzoxazolyl)oxy]- phenoxy]propanoic addfenuron N,N-dimethyl-N'-phenylureafenuron TCA Salt of fenuron and TCAflamprop N-benzoyl-N-(3-chloro-4-fluorophenyl)- DL-alaninefluazifop (.+-.)-2-[4-[[5-(trifluoromethyl)-2-pyri- dinyl]oxy]phenoxy]propanoic acidfluazifop-P (R)-2-[4-[[5-(trifluoromethyl)-2-pyri- dinyl]oxy]phenoxy]propanoic acidfluchloralin N-(2-chloroethyl)-2,6-dinitro-N-propyl- 4-(trifluoromethyl)benzenammefluometuron N,N-dimethyl-N-[3-(trifluoromethyl)- phenyl]ureafluorochlor- 3-chloro-4-(chloromethyl)-1-[3-(tri-idone fluoromethyl)phenyl]-2-pyrrolidinonefluorodifen p*-nitrophenyl a,a,a-trifluoro-2-nitro- p*-tolyl etherfluorogly- carboxmethyl 5-[2-chloro-4-(tri-cofen fluoromethyl)phenoxy]-2-nitrobenzoatefluridone 1-methyl-3-phenyl-5-[3-(trifluoro- methyl)phenyl]-4(1H)-pyridinonefomesafen 5-[2-chloro-4-(trifluoromethyl)phenoxy]- N-(methylsulfonyl)-2-nitrobenzamidefosamine ethyl hydrogen (aminocarbonyl)- phosphateglyphosate N-(phosphonomethyl)glycinehaloxyfop 2-[4-[[3-chloro-5-(trifluoromethyl)-2- pyridinyl]oxy]phenoxy]propanoic acidhexaflurate potassium hexafluoroarsenatehexazinone 3-cyclohexyl-6-(dimethylamino)-1-methyl- 1,3,5-triazine-2,4(1H,3H)-dioneimazametha- 6-(4-isopropyl-4-methyl-5-oxo-2-benz imidazolin-2-yl)-m*-toluic acid, methyl ester and 6-(4-isopropyl- 4-methyl-5-oxo-2-imidazohn-2-yl)- p*-toluic acid, methyl esterimazapyr (.+-.)-2-[4,5-dihydro-4-methyl-4-(1-methyl- ethyl)-5-oxo-1H-imidazol-2-yl]-3- pyridinecarboxylic acidimazaquin 2-[4,5-dihydro-4-methyl-4-(1-methyl- ethyl)-5-oxo-1H-imidazol-2-yl]-3- quinolinecarboxylic addimazethapyr (.+-.)-2-[4,5-dihydro-4-methyl-4-(1-methyl- ethyl)-5-oxo-1H-imidazol-2-yl]-5- ethyl-3-pyridinecarboxyhc acidixoynil 4-hydroxy-3,5-diiodobenzonitrileisopropalin 4-(1-methylethyl)-2,6-dinitro-N,N- dipropylbenzenamineisoproturon N-(4-isopropylphenyl)-N,N'-dimethylureaisouron N'-[5-(1,1-dimethylethyl)-3-isoxazolyl]- N,N-dimethylureaisoxaben N-[3-(1-ethyl-1-methylpropyl)-5- isoxazolyl]-2,6-dimethoxybenzamidekarbutilate 3-[[(dimethylamino)carbonyl]amino]- phenyl-(1,1-dimethylethyl)carbamatelactofen (.+-.)-2-ethoxy-1-methyl-2-oxoethyl 5-[2- chloro-4-(trifluoromethyl)phenoxy]- 2-nitrobenzoatelenacil 3-cyclohexyl-6,7-dihydro-1H-cyclopenta- pyrimidine-2,4(3H,5H)-dionelinuron N-(3,4-dichlorophenyl)-N-methoxy-N- methylureaMAA methylarsonic acidMAMA monoammonium salt of MAAMCPA (4-chloro-2-methylphenoxy)acetic acidMCPB 4-(4-chloro-2-methylphenoxy)butanoic acidMON 7200 S,S-dimethyl-2-(difluoromethyl)-4- (2-methylpropyl)-6-(trifluoromethyl)- 3,5-pyridinedicarbothionatemecoprop (.+-.)-2-(4-chloro-2-methylphenoxy)- propanoic acidmefenacet 2-(2-benzothiazolyloxy-N-methyl-N- phenylacetamidemefluidide N-[2,4-dimethyl-5-[[(trifluoromethyl)- sulfonyl]amino]phenyl]acetamidemethal- N-(2-methyl-2-propenyl)-2,6-dinitro-N-propalin propyl-4-(trifluoromethyl)benzenamidemethabenz- 1,3-dimethyl-3-(2-benzothiazolyl)ureathiazuronmetham methylcarbamodithioic addmethazole 2-(3,4-dichlorophenyl)-4-methyl-1,2,4- oxadiazolidine-3,5-dionemethoxuron N'(3-chloro-4-methoxyphenyl)-N,N- dimethylureametolachlor 2-chloro-N-(2-ethyl-6-methylphenyl)-N- (2-methoxy-1-methylethyl)acetamidemetribuzin 4-amino-6-(1,1-dimethylethyl)-3-(methyl- thio)-1,2,4-triazin-5(4H)-onemetsulfuron 2-[[[[(4-methoxy-6-methyl-1,3,5-tri-methyl azin-2-yl)amino]carbonyl]- amino]sulfonyl]benzoic acid, methyl esterMH 1,2-dihydro-3,6-pyridazinedionemolinate S-ethyl hexahydro-1H-azepine-1-carbo- thioatemonolinuron 3-(p*-chlorophenyl)-1-methoxy-1-methyl- ureamonuron N'-(4-chlorophenyl)-N,N-dimethylureamonuron TCA Salt of monuron and TCAMSMA monosodium salt of MAAnapropamide N,N-diethyl-2-(1-naphthalenyloxy)- propanamidenaptalam 2-[(1-naphthalenylamino)carbonyl]- benzoic acidneburon 1-butyl-3-(3,4-dichlorophenyl)-1-methyl- ureanicosulfuron 2-[[(4,6-dimethoxypyrimidin-2-yl)- aminocarbonyl]aminosulfonyl]-N,N- dimethyl-3-pyridinecarboxamidenitralin 4-(methylsulfonyl)-2,6-dinitro-N,N- dipropylanilinenitrofen 2,4-dichloro-1-(4-nitrophenoxy)benzenenitrofluorfen 2-chloro-1-(4-nitrophenoxy)-4-(tri- fluoromethyl)benzenenorea N,N-dimethyl-N'-(octahydro-4,7-methano- 1H-inden-5-yl)urea 3aa,- 4a,5a,7a,7aa-isomernorflurazon 4-chloro-5-(methylamino)-2-[3-(tri- fluoromethyl)phenyl]-3(2H)- pyridazinoneoryzalin 4-(dipropylamino)-3,5-dinitro- benzenesulfonamideoxadiazon 3-[2,4-dichloro-5-(1-methylethoxy)- phenyl]-5-(1,1-dimethylethyl)- 1,3,4-oxadiazol-2(3H)-oneoxyfluorfen 2-chloro-1-(3-ethoxy-4-nitrophenoxy)-4- (trifluoromethyl)benzeneparaquat 1,1'-dimethyl-4,4'-dipyridinium ionpebulate S-propyl butylethylcarbamothioatependimethalin N-(1-ethylpropyl)-3,4-dimethyl-2,6- dinitrobenzenamineperfluidone 1,1,1-trifluoro-N-[2-methyl-4-(phenyl- sulfonyl)phenyl]methanesulfonamidephenmedipham 3-[(methoxycarbonyl)amino]phenyl (3- methylphenyl)carbamatepicloram 4-amino-3,5,6-trichloro-2-pyridine- carboxylic acidPPG-1013 5-[2-chloro-4-(trifluoromethyl)- phenoxy]-2-nitroacetophenone oxime-O-acetic acid, methyl esterpretilachlor a-chloro-2,6-diethyl-N-(2-propoxy- ethyl)acetanilideprocyazine 2-[[4-chloro-6-(cyclopropylamino)-1,3,5- triazine-2-yl]amino]-2-methylpropane- nitrileprofluralin N-(cyclopropylmethyl)-2,6-dinitro-N- propyl-4-(trifluoromethyl)benzenamineprometon 6-methoxy-N,N'-bis(1-Methylethyl)-1,3,5- triazine-2,4-diamineprometryn N,N'-bis(1-methylethyl)-6-(methylthio)- 1,3,5-triazine-2,4-diaminepronamide 3,5-dichloro-N-(1,1-dimethyl-2-propyn- yl)benzamidepropachlor 2-chloro-N-(1-methylethyl)-N- phenylacetamidepropanil N-(3,4-dichlorophenyl)propanamidepropazine 6-chloro-N,N'-bis(1-methylethyl)- 1,3,5-triazine-2,4-diaminepropham 1-methylethyl phenylcarbamateprosulfalin N-[[4-(dipropylamino)-3,5-dinitro- phenyl]sulfonyl]-S,S-dimethylsulfil- imineprynachlor 2-chloro-N-(1-methyl-2-propynyl)acet- anilidepyrazolate 4-(2,4-dichlorobenzoyl)-1,3-dimethyl- pyrazol-5-yl-p*-toluenesulphonatepyrazon 5-amino-4-chloro-2-phenyl-3(2H)- pyridazinonepyrazosulfuron ethyl S-[3-(4,6-dimethoxypyrimidin-2-ethyl yl)ureadosulfonyl]-1-methylpyrazole- 4-carboxylatequinclorac 3,7-(dichloro-8-quinoline carboxylic acidquizalofop (.+-.)-2-[4-[(6-chloro-2-quinoxalinyl)-ethyl oxy]phenoxy]propanoic acid, ethyl estersecbumeton N-ethyl-6-methoxy-N'-(1-methylpropyl)- 1,3,5-triazine-2,4-diamidesethoxydim 2-[1-(ethoxyimino)butyl]-5-[2-(ethyl- thio)propyl]-3-hydroxy-2-cyclohexen- 1-onesiduron N-(2-methylcyclohexyl)-N'-phenylureasimazine 6-chloro-N,N'-diethyl-1,3,5-triazine- 2,4-diamineSK-233 1-(a,a-dimethylbenzyl)-3-(4-methyl- phenyl)ureasulfometuron 2-[[[[(4,6-dimethyl-2-pyrimidinyl)-methyl amino]carbonyl]amino]sulfonyl]- benzoic acid, methyl eaterTCA trichloroacetic acidtebuthiuron N-[5-(1,1-dimethylethyl)-1,3,4-thiadi- azol-2-yl]-NIN'-dimethylureaterbacil 5-chloro-3-(1,1-dimethylethyl)-6- methyl-2,4(1H,3H)-Pyrimidinedioneterbuchlor N-(butoxymethyl)-2-chloro-N-12-(1,1- dimethylethyl)-6-methylphenyl]- acetamideterbuthyl- 2-(tert*-butylamino)-4-chloro-6-(ethyl-azine amino)-s*-triazineterbutol 2,6-di-tert*-butyl-p*-tolyl methylcar- bamateterbutryn N-(1,1-dimethylethyl)-N'-ethyl-6- (methylthio)-1,3,5-triazine- 2,4-diaminethifensul- 3-[[[[(4-methoxy-6-methyl-1,3,5-triazin-furon 2-yl)amino]carbonyl]amino]sulfonyl]-methyl 2-thiophenecarboxylic acid, methyl esterthiobencarb S-[(4-chlorophenyl)methyl] diethylcar- bamothioatetriallate S-(2,3,3-trichloro-2-propenyl) bis(1- methylethyl)carbamothioatetribenuron 2-[[[[N-(4-methoxy-6-methyl-1,3,5-methyl triazine-2-yl)-N-methylamino]- carbonyl]amino]sulfonyl]benzoic acid, methyl estertriclopyr [(3,5,6-trichloro-2-pyridinyl)- oxy]acetic acidtridiphane 2-(3,5-dichlorophenyl)-2-(2,2,2- trichloroethyl)oxiranetrifluralin 2,6-dinitro-N,N-dipropyl-4-(tri- fluoromethyl)benzenaminetrimeturon 1-(p*-chlorophenyl)-2,3,3-trimethylpseu- dourea2,4-D (2,4-dichlorophenoxy)acetic acid2,4-DB 4-(2,4-dichlorophenoxy)butanoic acidvernolate S-propyl dipropylcarbamothioatexylachlor 2-chloro-N-(2,3-dimethylphenyl)-N- (1-methylethyl)acetamide______________________________________
Herbicidal properties of the subject compounds were discovered in a number of greenhouse tests. Test procedures and results follow.
TEST A
Seeds of barley (Hordeum vulgare), barnyardgrass (Echinochloa crus-galli), blackgrass (Alopecurus myosuroides), cheatgrass (Bromus secalinus), chickweed (Stellaria media), cocklebur (Xanthium pensylvanicum), corn (Zea mays), cotton (Gossypim hirsutum), crabgrass (Digitaria spp.), bedstraw (Galium aparine), giant foxtail (Setaria faberii), lambsquarters (Chenopodium album), morningglory (Ipomoea hederacea), rape (Brassica napus), rice (Oryza sativa), sorghum (Sorghum bicolor), soybean (Glycine max), sugar beet (Beta vulgaris), velvetleaf (Abutilon theophrasti), wheat (Triticum aestivum), wild buckwheat (Polygonum convolvulus), and wild oat (Avena fatua) and purple nutsedge (Cyperus rotundus) tubers were planted and treated preemergence with test chemicals dissolved in a non-phytotoxic solvent. At the same time, these crop and weed species were also treated with postemergence applications of test chemicals. Plants ranged in height from two to eighteen cm (one to four leaf stage) for postemergence treatments. Treated plants and controls were maintained in a greenhouse for twelve to sixteen days, after which all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table A, are based on a scale of 0 to 10 where 0 is no effect and 10 is complete control. A dash (-) response means no test result.
TABLE A - TEST A COMPOUND Rate (200 g/ha) 165 166 167 168 169 170 171 POSTEMERGENCE Barley 9 9 9 7 9 9 9 Barnyardgrass 9 9 10 9 9 9 9 Bedstraw 8 9 9 9 10 10 8 Blackgrass 9 9 9 9 10 10 9 Cheatgrass 8 10 9 8 9 9 9 Chickweed 9 10 10 9 9 9 3 Cocklebur 9 9 9 -- 10 10 7 Corn 10 10 10 10 9 10 9 Cotton 9 10 10 9 9 10 9 Crabgrass 9 10 8 5 10 10 8 Giant foxtail 9 10 9 9 10 10 9 Lambsquarters 10 10 10 10 10 10 9 Morningglory 10 10 10 10 10 10 8 Nutsedge 9 9 9 10 10 9 0 Rape 9 9 10 9 9 9 5 Rice 9 9 9 9 9 10 9 Sorghum 9 10 10 10 10 10 9 Soybean 9 9 9 9 9 9 9 Sugar beet 9 9 10 9 9 9 10 Velvetleaf 9 9 9 9 9 9 7 Wheat 10 8 9 8 9 9 9 Wild buckwheat 10 10 10 9 9 10 8 Wild oat 9 9 10 8 9 10 10 COMPOUND Rate (200 g/ha) 165 166 167 168 169 170 171 PREEMERGENCE Barley 8 9 8 2 3 2 2 Barnyardgrass 9 9 9 9 9 9 7 Bedstraw 7 7 9 6 8 9 4 Blackgrass 7 8 9 8 3 9 0 Cheatgrass 8 8 9 8 4 8 0 Chickweed 9 9 9 8 9 9 2 Cocklebur -- 8 6 1 2 8 2 Corn 7 9 9 8 8 7 3 Cotton 8 8 7 3 5 9 2 Crabgrass 9 9 8 7 9 9 9 Giant foxtail 9 9 9 7 9 9 9 Lambsquarters 9 9 9 8 9 9 7 Morningglory 0 6 5 4 4 9 0 Nutsedge 9 9 9 9 0 10 3 Rape 9 9 9 9 9 9 2 Rice 9 9 9 9 10 9 9 Sorghum 9 9 9 9 9 9 7 Soybean 8 9 8 4 7 8 5 Sugar beet 9 9 9 8 9 9 7 Velvetleaf 3 8 8 8 1 7 2 Wheat 8 9 9 5 7 9 2 Wild buckwheat 7 7 8 3 7 9 0 Wild oat 8 8 9 3 4 6 0 COMPOUND Rate (100 g/ha) 93 POSTEMERGENCE Barley 4 Bedstraw 6 Blackgrass 5 Cheatgrass 4 Chickweed 2 Lambsquarters 9 Rape 4 Sugar beet 8 Wheat 5 Wild buckwheat 9 Wild oat 5 COMPOUND Rate (100 g/ha) 93 PREEMERGENCE Barley 0 Bedstraw 0 Blackgrass 2 Cheatgrass 0 Chickweed 8 Lambsquarters 5 Rape 0 Sugar beet 5 Wheat 0 Wild buckwheat 0 Wild oat 0 COMPOUND Rate (50 g/ha) 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 2 3 24 25 26 27 28 29 POSTEMERGENCE Barley 9 8 7 7 8 9 9 9 8 8 9 8 9 9 2 4 0 7 8 4 5 3 9 8 9 9 9 9 9 Barnyardgrass 9 9 9 9 10 9 9 9 9 9 10 10 10 9 2 3 2 7 9 7 2 7 9 8 9 9 9 9 10 Bedstraw 9 9 10 9 10 9 7 9 4 5 8 4 7 5 5 3 0 2 5 6 6 6 7 9 8 9 8 8 10 Blackgrass 8 8 9 8 9 9 9 8 8 9 9 9 9 9 7 4 3 8 9 3 8 5 10 8 10 10 9 9 8 Cheatgrass 9 9 9 7 9 9 9 9 8 9 9 9 9 5 6 4 5 7 7 4 8 3 9 6 9 10 9 9 9 Chickweed 9 8 9 8 9 9 6 9 10 10 10 -- -- 10 -- -- -- -- 10 8 9 7 10 10 10 10 10 7 10 Cocklebur 9 9 6 5 8 3 0 3 9 9 9 8 9 2 0 8 7 3 5 3 3 0 8 0 -- -- -- -- -- Corn 9 9 10 9 10 9 9 9 9 9 9 9 10 9 7 7 7 9 9 9 6 7 10 9 9 9 10 9 10 Cotton 9 9 9 9 9 9 10 9 9 9 9 9 9 9 4 5 0 4 9 5 3 1 9 9 9 9 10 9 9 Crabgrass 9 9 9 6 10 5 6 6 -- -- -- -- -- -- -- -- -- -- -- 5 3 0 7 9 8 9 9 7 9 Giant foxtail 9 9 9 6 9 9 9 7 9 8 10 8 10 10 7 3 2 7 8 6 8 8 9 9 9 9 9 9 10 Lambsquarters 9 9 9 9 10 9 9 9 9 9 9 10 10 9 4 8 7 6 7 9 9 8 9 7 10 10 10 10 10 Morningglory 9 9 10 9 10 9 9 9 7 9 10 9 10 9 8 5 7 7 9 8 2 3 9 9 10 9 9 9 10 Nutsedge 9 9 10 9 10 9 3 7 8 9 5 6 2 5 0 0 0 0 2 4 7 0 3 5 -- 9 9 9 -- Rape 6 9 9 8 9 9 0 0 7 9 9 8 9 9 0 8 2 0 9 7 9 7 9 10 9 9 9 9 9 Rice 9 9 9 9 9 9 9 9 9 9 9 9 10 9 9 6 8 9 9 9 9 9 9 9 9 9 9 9 9 Sorghum 9 9 9 9 9 9 9 9 9 9 9 10 9 9 7 6 6 9 9 9 9 6 9 9 9 9 10 9 10 Soybean 9 9 9 7 9 9 8 9 9 9 9 9 9 9 3 3 4 5 6 8 7 0 9 9 9 9 9 9 9 Sugar beet 9 10 9 7 9 9 7 9 8 9 9 8 9 9 2 3 3 3 8 9 9 4 9 10 10 10 10 9 10 Velvetleaf 9 9 9 9 10 7 6 9 4 8 9 7 9 9 2 0 0 6 9 6 8 2 9 9 9 9 10 9 9 Wheat 9 8 6 7 7 9 8 8 9 9 9 8 9 9 2 1 0 8 9 4 5 3 9 9 8 9 9 8 9 Wild buckwheat 9 9 9 9 9 9 6 9 7 7 9 8 7 8 0 0 0 3 3 8 8 3 8 8 9 9 9 9 10 Wild oat 9 9 9 7 8 9 9 8 9 10 9 9 10 9 4 1 0 7 7 6 7 2 9 9 9 10 10 9 10 COMPOUND Rate (50 g/ha) 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 4 9 50 51 52 53 54 55 56 57 58 POSTEMERGENCE Barley 9 9 8 8 9 8 9 6 6 3 0 8 5 3 0 0 0 4 2 4 7 8 9 9 6 3 7 8 7 Barnyardgrass 9 9 9 8 9 9 9 2 8 3 3 9 6 1 3 1 3 1 1 6 9 9 -- 9 9 9 9 9 9 Bedstraw 8 7 6 6 5 8 9 4 7 9 5 9 7 0 5 0 0 3 2 6 9 10 2 7 8 7 8 9 9 Blackgrass 7 8 7 6 9 10 9 0 3 2 0 4 3 4 2 2 0 3 0 0 9 9 2 9 7 7 8 9 9 Cheatgrass 9 8 7 8 9 8 8 4 5 3 0 6 5 2 3 0 3 5 0 2 9 9 3 9 7 6 7 8 9 Chickweed 9 6 6 9 10 8 10 6 9 -- 3 10 10 -- 10 0 2 9 4 9 9 10 4 10 10 8 3 10 9 Cocklebur -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- 10 10 -- 10 10 9 9 10 9 Corn 10 9 9 9 9 9 9 8 9 9 4 9 9 3 7 1 6 9 7 9 9 9 -- 9 9 5 9 9 9 Cotton 10 9 9 8 8 9 9 0 7 9 5 9 9 0 3 0 0 2 0 9 9 9 -- 9 9 9 9 9 9 Crabgrass 9 7 1 2 7 8 9 3 0 0 0 3 1 0 0 3 0 0 2 1 3 9 -- 9 4 0 0 4 1 Giant foxtail 10 9 7 7 9 9 9 2 4 2 0 8 4 1 0 0 0 3 0 2 9 9 -- 9 7 1 3 9 9 Lambsquarters 10 8 10 9 9 9 10 9 9 9 9 -- 8 4 7 9 8 2 5 9 10 10 7 10 10 8 7 -- 10 Morningglory 9 9 9 9 9 9 9 8 9 8 4 10 9 5 8 6 6 5 7 9 10 10 -- 9 10 9 0 9 9 Nutsedge -- 2 0 0 0 0 8 -- 6 8 0 5 0 0 0 0 -- 0 0 0 9 10 -- 9 9 -- 9 9 10 Rape 10 7 3 8 8 1 9 7 8 8 8 10 10 2 2 0 4 6 0 9 9 10 8 9 9 9 9 9 10 Rice 9 9 9 9 10 9 9 8 8 7 2 9 9 4 3 1 3 9 4 8 9 10 -- 9 9 8 9 9 9 Sorghum 10 9 9 9 9 9 9 4 8 2 0 9 4 1 1 0 0 3 1 3 8 9 -- 9 9 3 9 9 9 Soybean 9 9 9 5 8 8 9 4 8 7 2 9 9 2 3 0 2 3 2 9 9 9 -- 9 9 6 8 9 9 Sugar beet 10 9 8 9 9 9 9 9 10 8 9 10 9 3 9 8 8 9 8 9 10 9 7 9 9 8 7 9 9 Velvetleaf 9 7 8 7 6 8 9 9 9 9 2 9 8 1 7 2 0 1 4 5 9 10 -- 9 8 9 9 10 10 Wheat 9 8 7 8 9 8 9 2 3 2 0 8 6 1 1 1 2 3 0 3 7 9 8 9 2 2 3 7 7 Wild buckwheat 10 3 0 6 3 6 8 8 7 9 9 9 9 0 3 2 0 5 2 6 7 10 2 8 8 7 -- 8 7 Wild oat 10 9 9 9 9 9 9 3 6 4 0 9 6 1 0 0 0 5 0 3 8 9 8 8 7 0 8 8 7 COMPOUND Rate (50 g/ha) 59 60 61 62 63 64 65 66 67 68 69 70 71 72 73 74 75 76 77 7 8 79 80 81 82 83 84 85 86 87 POSTEMERGENCE Barley 8 7 2 8 9 8 8 6 3 9 0 5 0 0 7 7 4 2 8 6 5 2 9 9 8 8 8 -- 4 Barnyardgrass 8 7 5 9 9 9 9 8 9 9 8 9 5 3 9 9 4 1 9 9 7 0 9 9 9 9 4 9 4 Bedstraw 9 10 8 5 8 8 7 8 8 5 7 9 9 6 7 9 8 8 6 8 4 2 6 8 9 8 8 -- 3 Blackgrass 8 8 5 9 10 10 9 9 8 7 1 7 5 3 9 9 6 2 9 9 8 3 9 9 10 9 9 -- 8 Cheatgrass 9 8 6 9 10 10 9 7 9 9 8 3 2 3 9 9 2 3 9 9 4 2 9 9 10 9 8 -- 8 Chickweed 10 10 8 5 10 9 9 0 9 -- 9 9 9 -- 9 9 10 9 10 9 4 0 9 10 10 9 7 -- 2 Cocklebur 10 10 9 9 10 10 9 9 10 9 9 -- 9 8 9 9 9 -- -- -- -- -- -- -- -- -- -- -- -- Corn 9 9 3 0 9 9 9 9 3 9 5 9 9 2 7 9 9 7 5 9 6 2 0 7 9 9 9 1 0 Cotton 9 9 9 9 9 10 9 9 9 9 9 9 9 8 9 9 10 9 9 9 6 2 9 9 9 9 9 9 9 Crabgrass 6 0 0 5 5 9 10 4 2 6 2 6 3 0 4 5 2 0 6 7 0 0 5 7 -- 6 3 3 2 Giant foxtail 8 5 0 7 9 9 9 5 5 8 5 8 2 1 9 10 8 6 9 9 7 0 8 9 9 9 3 6 2 Lambsquarters 9 9 7 9 10 10 9 9 10 9 -- 9 9 8 9 9 9 8 9 9 8 3 10 10 10 10 9 -- 7 Morningglory 9 9 9 9 10 10 9 9 9 9 9 9 10 7 9 10 7 8 9 9 7 5 10 10 10 9 9 10 9 Nutsedge 10 10 9 9 9 10 6 7 9 -- 9 9 -- 5 8 10 5 0 10 10 0 0 3 9 10 7 0 8 0 Rape 9 9 10 9 10 9 9 8 10 9 9 10 9 7 9 9 9 9 9 9 9 7 9 9 9 9 9 -- 8 Rice 9 9 8 9 9 9 9 9 8 9 7 9 8 4 9 9 9 7 9 9 9 8 9 9 9 10 9 9 8 Sorghum 9 9 3 10 9 10 9 8 9 9 3 4 1 2 9 9 3 2 9 9 3 0 9 9 9 9 9 9 8 Soybean 9 9 7 9 9 9 9 8 9 9 9 9 9 1 9 9 8 8 9 9 6 3 9 9 9 9 9 9 6 Sugar beet 9 9 10 9 9 9 9 9 9 10 10 10 10 10 9 9 10 9 10 9 9 7 9 9 9 9 9 -- 7 Velvetleaf 9 9 9 9 9 10 9 9 9 9 9 9 9 8 9 9 9 8 9 9 5 0 9 10 10 9 9 9 9 Wheat 7 3 1 9 9 9 9 9 2 6 0 0 0 0 7 7 3 0 8 9 8 2 8 9 9 9 8 -- 4 Wild buckwheat 9 9 9 10 9 9 9 8 10 7 7 10 4 0 8 9 7 1 8 9 5 0 9 9 9 9 9 -- 7 Wild oat 8 7 0 9 9 9 10 9 3 8 0 2 0 0 9 9 8 2 9 9 9 2 9 8 4 9 9 -- 3 COMPOUND Rate (50 g/ha) 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 POSTEMERGENCE Barley 7 8 8 3 3 8 8 9 8 8 8 6 4 7 9 9 9 9 3 9 9 9 9 9 8 Barnyardgrass 9 9 7 0 5 9 9 9 9 8 8 7 7 6 9 9 9 8 4 9 9 9 9 9 9 Bedstraw 8 -- 8 8 7 8 9 9 8 7 9 7 7 5 9 9 7 8 7 9 9 9 9 8 9 Blackgrass 8 9 9 9 9 9 9 9 9 9 9 9 9 8 9 9 9 9 5 9 9 9 10 9 9 Cheatgrass 8 9 8 7 9 9 9 9 6 8 9 4 3 6 9 9 9 9 5 9 9 9 9 9 9 Chickweed 10 9 9 10 3 9 9 9 10 9 9 9 9 3 9 10 3 7 2 10 9 10 9 10 -- Cocklebur -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Corn 5 9 9 9 0 9 9 9 9 9 9 9 7 0 0 0 0 9 0 9 9 9 9 9 6 Cotton 9 10 9 9 9 9 9 9 10 9 9 9 9 2 8 9 5 8 4 10 9 10 10 10 10 Crabgrass 5 6 6 2 0 8 7 8 5 3 5 2 1 2 3 1 5 7 0 9 9 9 9 8 -- Giant foxtail 5 8 8 3 0 9 9 9 9 8 9 5 4 3 7 7 7 8 0 9 7 9 10 9 6 Lambsquarters 8 9 9 -- 5 9 9 10 9 9 -- 8 7 8 9 10 3 8 -- 10 10 10 10 10 9 Morningglory 10 9 9 9 9 9 10 9 9 9 10 9 9 8 9 9 9 9 8 9 9 8 10 10 9 Nutsedge 9 9 -- 0 -- -- -- -- -- -- -- -- -- -- 10 8 0 0 0 10 9 9 9 10 9 Rape 9 9 9 9 6 9 9 9 9 9 9 9 9 9 9 9 9 5 7 9 9 9 10 9 8 Rice 9 8 9 9 9 9 9 9 9 9 9 9 9 9 10 9 10 9 7 9 10 9 10 9 9 Sorghum 9 9 9 9 9 9 9 9 9 9 9 9 9 5 9 9 9 9 8 9 9 9 9 9 9 Soybean 9 8 9 9 3 9 9 9 9 8 9 9 9 0 3 9 0 2 1 9 9 9 9 9 9 Sugar beet 9 10 9 10 5 10 9 9 9 9 9 9 9 9 9 9 8 9 9 9 9 9 9 9 8 Velvetleaf 10 10 8 9 6 9 9 9 9 8 9 10 9 7 7 9 5 5 2 10 9 10 10 10 10 Wheat 4 4 4 4 1 9 9 9 9 9 9 3 3 6 9 9 9 9 4 9 9 9 9 9 8 Wild buckwheat 7 9 9 9 5 -- -- -- -- 9 -- 9 9 6 9 -- -- -- -- 10 10 10 -- -- 9 Wild oat 4 2 7 7 0 9 9 9 9 9 9 9 8 6 9 9 9 9 0 9 9 9 9 7 6 COMPOUND Rate (50 g/ha) 113 114 115 116 117 118 119 120 121 122 123 124 125 126 127 128 129 130 131 132 133 134 POSTEMERGENCE Barley 7 8 7 6 3 0 9 8 9 9 7 8 4 3 0 2 0 1 1 3 1 2 Barnyardgrass 9 9 9 9 7 5 9 9 9 9 5 9 3 9 0 2 0 5 0 0 0 0 Bedstraw 8 9 10 8 9 8 8 7 8 9 3 2 3 7 9 2 3 6 7 8 8 7 Blackgrass 9 9 9 10 8 9 9 9 9 9 4 7 4 6 4 4 2 6 6 7 6 3 Cheatgrass 9 8 9 8 8 5 9 9 9 9 7 8 7 5 2 2 0 6 6 3 2 0 Chickweed 2 7 9 9 9 4 10 9 10 9 4 9 8 9 5 2 4 10 9 10 2 0 Cocklebur -- -- -- -- -- -- -- -- -- -- 6 9 10 10 6 10 4 9 10 10 9 9 Corn 9 9 9 9 4 0 9 9 9 9 0 5 2 9 7 0 0 6 5 9 7 2 Cotton 9 9 10 10 10 9 9 10 10 9 9 9 10 10 9 9 9 9 9 9 9 2 Crabgrass 5 8 4 6 0 3 9 8 9 9 2 4 2 2 2 0 0 0 0 0 0 0 Giant foxtail 7 9 7 8 2 2 9 9 9 9 2 3 1 3 1 0 0 2 2 0 0 0 Lambsquarters -- -- 9 9 9 7 -- -- 10 -- 9 10 -- 10 9 9 7 9 10 10 10 -- Morningglory 8 9 10 10 10 9 10 10 10 10 5 9 10 9 10 9 1 6 9 10 10 9 Nutsedge -- 9 9 10 7 9 9 9 9 9 -- 8 9 9 7 8 -- 8 10 9 7 3 Rape 9 9 9 9 9 9 9 9 10 9 8 9 9 9 9 9 8 8 9 9 9 9 Rice 9 9 8 9 9 7 9 9 9 9 8 8 7 9 9 4 0 8 2 8 9 0 Sorghum 9 9 9 9 9 7 9 9 9 9 1 5 3 8 8 9 0 6 7 8 9 0 Soybean 2 9 9 9 9 1 9 9 9 9 7 9 8 8 8 3 6 9 9 9 9 1 Sugar beet 5 9 8 10 9 7 9 9 9 9 8 10 10 10 10 9 8 9 9 9 9 6 Velvetleaf 9 10 10 10 10 9 10 10 10 9 10 9 9 10 2 9 9 9 10 10 6 9 Wheat 3 5 7 3 0 0 9 9 9 9 2 2 0 0 0 2 0 0 0 2 1 0 Wild buckwheat 5 8 9 9 9 7 9 9 9 9 7 8 9 9 9 9 6 7 9 9 8 9 Wild oat 9 9 9 8 5 2 9 7 9 9 7 6 2 3 2 2 1 0 3 4 3 2
TABLE A - TEST A COMPOUND Rate (50 g/ha) 135 136 137 138 139 140 141 142 143 144 145 146 147 148 149 150 151 152 165 166 167 168 POSTEMERGENCE Barley 9 7 8 9 7 9 8 9 8 9 5 7 9 9 9 9 7 5 8 8 9 3 Barnyardgrass 9 7 9 9 7 9 9 9 9 9 0 9 9 9 9 8 5 8 9 9 9 9 Bedstraw 9 9 9 9 8 7 8 9 9 9 7 8 9 9 9 9 9 9 7 9 9 9 Blackgrass 9 4 8 9 7 9 9 9 9 9 8 9 9 9 9 9 9 9 8 9 8 7 Cheatgrass 9 8 9 9 8 9 8 9 9 9 3 9 9 9 9 9 8 9 8 9 9 7 Chickweed 8 0 8 8 4 7 4 9 10 8 4 7 9 10 10 9 8 7 9 10 9 8 Cocklebur 9 9 8 9 9 9 9 10 10 9 8 10 10 10 10 10 9 10 9 9 9 8 Corn 8 8 9 9 5 9 2 9 9 9 8 8 0 6 9 9 9 3 9 10 10 9 Cotton 9 9 9 9 9 9 9 9 10 9 9 9 10 10 9 9 9 9 9 10 10 9 Crabgrass 2 2 3 6 0 2 1 6 9 3 0 2 3 2 6 2 2 2 9 8 4 3 Giant foxtail 7 4 7 9 6 9 3 8 9 9 2 5 7 6 9 9 6 3 9 9 9 9 Lambsquarters 8 9 9 9 -- 9 9 9 10 9 9 10 10 10 10 10 9 9 10 9 10 9 Morningglory 9 9 10 9 10 10 2 9 9 9 9 9 10 9 10 10 10 10 5 10 10 10 Nutsedge 6 8 9 -- 6 8 9 9 10 9 0 9 9 9 9 9 7 8 8 9 9 9 Rape 2 9 7 2 2 3 9 9 9 9 9 9 9 10 9 9 9 9 9 9 9 9 Rice 9 9 9 9 9 9 9 9 10 10 9 9 9 9 10 9 10 9 9 9 9 9 Sorghum 9 9 9 9 7 9 9 9 10 10 9 9 9 9 9 9 9 9 9 9 10 9 Soybean 9 9 8 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 Sugar beet 9 8 9 9 8 9 9 8 10 9 9 9 8 9 9 9 9 9 9 10 10 9 Velvetleaf 9 9 7 9 9 9 9 10 10 8 4 10 10 10 10 9 9 9 9 9 9 8 Wheat 8 8 9 9 8 9 9 9 9 9 9 8 9 9 9 9 8 4 7 8 8 6 Wild buckwheat -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- 9 7 9 8 Wild oat 9 8 9 9 5 9 9 9 9 9 9 8 9 8 9 9 9 3 8 9 9 4 COMPOUND Rate (50 g/ha) 169 170 171 172 173 174 175 176 177 178 179 180 181 182 183 184 185 186 187 188 189 190 POSTEMERGENCE Barley 7 4 9 9 9 8 9 8 9 9 7 8 8 9 9 9 9 9 9 8 9 9 Barnyardgrass 9 10 9 7 9 9 9 4 6 9 9 9 9 10 10 10 10 10 9 9 9 9 Bedstraw 8 10 6 8 9 8 7 2 3 5 7 7 7 8 9 9 9 9 9 8 8 8 Blackgrass 9 10 9 9 9 9 9 9 8 9 9 9 9 9 9 9 9 9 10 9 -- 9 Cheatgrass 8 8 8 9 9 8 8 7 7 8 8 7 7 9 9 9 9 9 9 7 9 8 Chickweed 9 9 2 8 8 5 9 3 3 9 7 8 8 4 8 9 9 8 9 4 4 9 Cocklebur 9 9 7 9 9 9 7 2 6 2 6 1 6 9 10 10 10 10 9 3 9 9 Corn 10 10 9 9 10 10 9 9 9 9 8 10 10 10 10 10 9 10 10 9 9 9 Cotton 9 9 8 9 9 8 9 0 2 9 2 8 9 9 10 9 9 9 9 8 9 9 Crabgrass 9 9 8 8 9 7 9 6 7 9 6 9 9 9 10 10 9 10 9 8 9 8 Giant foxtail 9 10 9 9 9 9 9 8 9 9 6 9 9 9 10 10 9 10 9 9 9 9 Lambsquarters 10 9 9 10 10 10 10 5 7 7 7 6 7 10 10 10 10 9 10 7 8 9 Morningglory 10 10 9 9 9 9 9 2 6 8 5 9 9 9 10 10 10 10 9 9 9 9 Nutsedge 7 3 0 9 8 9 3 0 0 9 -- 2 -- 8 9 9 9 9 -- 2 9 5 Rape 9 9 2 7 9 8 8 0 0 2 7 2 7 9 9 9 9 10 9 0 3 0 Rice 9 10 9 9 9 10 10 7 9 9 8 9 9 10 10 10 10 10 10 9 9 9 Sorghum 10 10 9 9 9 9 9 6 8 9 6 9 9 9 9 10 9 10 9 9 9 9 Soybean 9 9 9 9 9 9 9 1 8 9 7 9 9 9 9 9 9 9 9 6 8 9 Sugar beet 9 9 9 9 9 8 8 0 7 8 7 8 9 9 10 9 8 9 9 9 8 9 Velvetleaf 9 9 6 9 9 9 9 0 2 6 3 9 9 9 10 10 9 9 9 6 6 7 Wheat 9 9 9 9 9 4 9 8 8 9 8 8 9 9 9 9 7 9 9 7 8 8 Wild buckwheat 9 10 6 9 9 9 -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Wild oat 9 9 8 9 9 3 9 9 7 9 8 8 8 9 9 9 9 9 9 9 9 9 COMPOUND Rate (50 g/ha) 191 192 203 204 205 206 207 208 209 210 211 212 213 214 215 216 217 218 219 220 221 222 POSTEMERGENCE Barley 9 9 9 10 9 9 9 9 9 9 9 9 9 9 7 9 9 9 6 8 5 0 Barnyardgrass 8 6 9 10 9 9 10 9 1 9 9 9 10 9 9 9 10 9 9 9 9 9 Bedstraw 7 7 9 9 9 9 9 9 5 8 10 10 10 10 9 6 7 8 8 8 6 7 Blackgrass 8 9 9 9 9 9 9 9 9 9 9 9 9 9 7 9 9 8 8 9 9 0 Cheatgrass 7 8 9 9 9 9 9 9 9 9 10 9 9 9 8 9 9 9 9 9 2 3 Chickweed 3 9 10 10 10 10 9 9 0 7 9 9 10 10 3 3 7 9 10 9 2 4 Cocklebur 9 9 -- 9 10 9 7 9 1 9 -- 9 9 8 -- -- 7 2 9 5 0 4 Corn 9 9 10 10 10 10 10 9 7 9 9 10 10 9 9 9 9 9 8 10 9 8 Cotton 9 9 9 9 10 9 9 9 5 9 10 10 10 10 10 9 10 10 9 9 8 9 Crabgrass 2 9 9 10 10 9 10 9 3 8 6 7 6 3 2 2 8 5 2 6 6 0 Giant foxtail 8 9 9 10 10 10 10 10 7 9 9 10 9 8 7 9 9 8 7 9 6 4 Lambsquarters 9 -- 10 10 10 10 10 10 5 9 10 10 10 10 9 9 10 10 9 9 5 10 Morningglory 9 9 9 9 10 9 10 9 7 9 9 10 9 10 9 9 10 10 10 9 7 10 Nutsedge 6 5 9 9 -- 8 10 10 -- 9 10 -- 9 -- 9 0 9 10 10 4 -- -- Rape 7 7 10 9 9 9 9 9 0 8 9 9 9 10 9 2 9 9 9 9 9 9 Rice 9 10 9 10 10 10 9 9 9 9 10 10 10 9 9 9 9 9 9 9 9 9 Sorghum 9 9 10 10 10 10 10 10 9 9 9 10 10 9 9 9 9 9 5 9 9 6 Soybean 9 9 9 9 9 9 8 9 1 9 9 9 9 9 9 7 9 9 9 9 9 8 Sugar beet 7 9 10 9 10 10 10 10 0 9 9 9 10 10 9 9 10 10 10 9 9 9 Velvetleaf 6 7 9 10 9 9 9 9 5 9 10 10 9 7 9 6 9 10 10 9 4 7 Wheat 8 9 10 10 9 10 9 9 8 9 9 9 9 9 8 8 9 9 6 9 9 2 Wild buckwheat -- -- 9 10 10 10 9 9 0 9 9 9 10 10 9 6 9 8 9 8 7 8 Wild oat 8 9 9 9 9 10 9 9 9 9 10 10 9 9 9 9 10 9 9 9 9 3 COMPOUND Rate (50 g/ha) 223 224 225 226 227 228 229 230 231 232 233 234 235 236 237 238 239 240 241 242 243 244 POSTEMERGENCE Barley 9 9 9 9 8 8 8 7 9 9 8 0 5 8 0 0 0 10 9 9 9 9 Barnyardgrass 9 9 9 9 9 9 9 7 9 6 7 2 7 9 0 0 3 9 9 10 9 10 Bedstraw 8 8 8 7 7 7 9 9 9 8 8 0 6 7 0 0 3 9 9 9 9 9 Blackgrass 7 8 9 9 3 9 9 9 9 9 9 2 8 9 0 2 2 9 9 9 10 10 Cheatgrass 8 8 9 7 5 8 9 9 9 9 8 0 8 8 0 0 0 9 9 10 9 9 Chickweed 9 7 10 9 1 2 9 7 9 9 3 0 5 6 0 0 0 9 9 10 10 10 Cocklebur 9 10 9 9 -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Corn 9 9 10 10 9 9 9 9 9 9 6 0 5 9 0 0 1 9 9 9 10 9 Cotton 9 10 10 8 9 9 9 9 9 9 8 0 3 5 0 0 -- 9 9 -- 10 10 Crabgrass 2 8 2 5 2 6 2 6 7 7 0 2 2 7 0 0 2 9 10 10 10 10 Giant foxtail 8 6 9 8 5 9 9 9 9 8 8 0 8 8 0 0 5 9 9 10 10 10 Lambsquarters 9 9 10 9 9 9 9 9 9 9 9 0 4 7 0 2 0 9 10 10 10 10 Morningglory 10 9 10 9 9 9 9 10 9 9 9 0 7 9 0 0 3 10 10 9 10 10 Nutsedge 9 9 5 0 -- 5 5 7 3 0 5 0 3 0 0 -- 0 10 8 10 9 9 Rape 8 9 10 10 9 5 8 9 9 9 9 0 7 8 0 0 5 9 9 9 9 9 Rice 9 9 9 9 9 10 9 9 9 10 9 9 9 9 0 0 8 10 9 10 10 10 Sorghum 9 8 10 9 8 9 9 9 9 9 9 3 3 9 0 0 3 9 9 10 10 10 Soybean 9 8 9 9 8 9 9 8 9 9 8 0 1 4 0 0 0 9 9 9 9 9 Sugar beet 9 9 10 9 7 3 5 5 9 9 4 0 3 7 3 0 0 9 9 9 9 10 Velvetleaf 9 9 9 9 8 9 9 10 9 8 8 0 6 8 0 0 0 10 10 10 9 10 Wheat 9 8 9 9 7 9 8 7 9 10 5 0 5 7 0 0 0 9 8 9 9 9 Wild buckwheat 6 8 9 8 7 -- -- 9 10 9 9 2 7 -- -- -- -- -- 10 -- 10 -- Wild oat 9 9 9 9 9 9 9 9 9 9 9 0 3 9 0 0 2 9 9 9 9 9 COMPOUND Rate (50 g/ha) 245 246 247 248 249 250 251 252 253 254 255 256 257 258 259 260 261 262 263 264 265 266 POSTEMERGENCE Barley 9 9 9 9 9 7 7 8 8 8 4 9 9 9 9 9 9 7 9 9 9 9 Barnyardgrass 9 9 9 9 9 8 9 9 9 7 8 9 9 10 9 9 9 9 9 8 9 9 Bedstraw 10 8 9 8 7 7 9 8 8 8 8 9 9 9 8 8 9 7 10 8 8 8 Blackgrass 9 9 10 9 9 9 9 9 9 9 9 9 10 9 9 9 9 8 5 9 9 10 Cheatgrass 9 8 9 8 5 5 8 9 8 8 7 10 10 9 9 9 10 8 8 8 9 9 Chickweed 9 8 9 10 9 0 8 5 9 10 3 10 10 10 8 8 10 9 9 5 5 7 Cocklebur -- -- -- -- -- 2 3 9 9 9 2 5 8 10 5 0 10 4 8 7 9 7 Corn 9 9 9 9 9 9 9 10 9 9 8 10 10 10 10 10 10 9 10 9 9 9 Cotton 10 10 10 9 10 8 9 9 10 10 8 9 8 9 9 8 8 4 10 8 7 9 Crabgrass -- 9 9 -- 8 2 6 7 7 2 0 9 8 9 7 9 8 0 3 2 2 2 Giant foxtail 10 9 10 9 9 6 9 9 9 7 4 9 9 9 9 9 9 9 8 7 9 9 Lambsquarters 10 10 10 10 9 5 8 8 10 10 -- -- 10 -- 10 10 10 -- -- -- -- 9 Morningglory 10 9 9 9 10 8 10 10 10 10 10 10 10 10 9 9 9 10 10 9 9 9 Nutsedge 10 8 10 7 8 0 -- -- 9 9 8 9 -- -- 0 0 -- -- 0 5 -- -- Rape 9 6 8 9 8 5 9 9 9 10 7 9 9 9 9 9 9 10 9 7 7 7 Rice 10 10 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 Sorghum 10 8 9 9 9 9 9 10 9 9 9 9 9 10 9 9 9 10 9 9 9 9 Soybean 9 5 8 9 9 7 9 9 9 9 7 9 9 9 9 9 9 9 9 9 9 9 Sugar beet 9 8 9 8 7 1 8 3 9 9 3 9 9 9 9 8 9 9 9 3 5 6 Velvetleaf 10 6 9 10 10 8 9 9 9 7 8 9 9 9 9 8 9 9 9 9 9 9 Wheat 9 8 8 9 9 7 8 8 6 5 3 9 9 9 9 9 9 5 9 9 8 8 Wild buckwheat -- -- -- -- -- 5 -- 9 9 9 8 9 9 9 8 8 9 8 8 8 8 9 Wild oat 9 9 9 8 9 7 8 9 9 8 3 10 9 9 10 9 9 8 9 9 9 9 COMPOUND Rate (50 g/ha) 267 268 269 270 271 272 273 274 275 276 277 278 279 280 281 282 283 284 285 286 287 288 POSTEMERGENCE Barley 9 9 8 9 9 9 9 9 9 8 7 5 3 9 0 6 9 9 9 9 9 9 Barnyardgrass 9 4 8 9 9 9 9 9 9 6 8 5 7 9 3 8 10 9 9 10 10 10 Bedstraw 9 9 8 9 10 9 7 6 9 5 7 4 7 6 8 8 9 9 9 9 9 9 Blackgrass 9 9 9 9 9 9 9 9 9 9 8 7 7 9 7 9 9 9 9 9 9 9 Cheatgrass 9 9 9 9 9 9 9 9 9 8 7 7 4 8 5 8 9 9 9 10 9 9 Chickweed 9 9 2 7 9 9 7 5 9 0 3 0 1 2 0 0 9 9 10 9 10 9 Cocklebur 9 10 0 5 7 8 0 1 10 2 3 0 4 6 0 7 -- -- -- -- -- -- Corn 9 9 9 10 10 10 9 9 9 9 7 0 0 8 2 6 9 9 9 9 9 9 Cotton 9 9 6 9 9 9 7 7 10 4 5 0 1 6 3 7 10 10 9 10 9 10 Crabgrass 4 4 0 9 9 9 8 3 9 3 3 0 0 3 0 0 9 9 9 9 9 10 Giant foxtail 9 8 5 9 9 9 8 9 9 5 3 0 0 9 2 4 10 9 10 10 10 10 Lambsquarters 10 10 8 10 10 10 8 7 10 9 8 5 7 -- 7 10 10 10 10 10 10 10 Morningglory 9 10 9 9 10 9 8 7 9 8 8 3 7 6 5 7 9 10 10 9 9 9 Nutsedge -- -- 3 9 9 -- -- -- 9 0 0 0 3 9 0 4 -- 9 6 9 9 9 Rape 9 9 9 9 9 9 9 8 9 0 0 3 3 0 4 7 9 9 9 9 9 9 Rice 9 9 9 9 9 9 9 9 10 9 9 9 9 9 9 8 10 9 10 10 10 9 Sorghum 9 9 9 9 9 9 9 9 9 9 9 8 6 8 8 8 9 9 10 10 10 10 Soybean 9 9 8 9 9 9 8 7 9 2 3 5 8 7 6 9 9 9 9 9 9 9 Sugar beet 9 9 1 9 9 9 7 7 9 8 9 8 3 7 7 8 9 9 9 9 9 9 Velvetleaf 9 9 8 9 9 9 3 3 8 3 5 2 2 4 0 7 10 9 10 10 9 10 Wheat 9 9 4 9 9 9 9 9 9 8 6 2 0 7 0 6 9 9 9 9 9 9 Wild buckwheat 9 9 9 9 10 9 8 7 9 2 -- 0 0 0 2 0 -- 9 9 9 9 9 Wild oat 9 9 6 9 9 9 9 9 9 9 8 5 0 8 0 7 9 9 9 9 9 9 COMPOUND Rate (50 g/ha) 289 290 291 292 293 294 295 296 297 298 299 300 301 302 303 304 305 306 307 308 309 310 POSTEMERGENCE Barley 9 9 9 8 9 7 5 8 5 4 6 9 9 9 9 9 9 8 9 8 8 8 Barnyardgrass 9 9 9 9 9 6 6 8 9 7 0 9 9 9 9 9 9 9 9 8 9 9 Bedstraw 8 7 8 7 7 6 7 7 7 5 3 7 8 8 6 6 7 7 7 8 6 9 Blackgrass 9 9 9 9 9 8 8 8 8 6 4 9 9 9 9 9 9 8 9 9 9 9 Cheatgrass 9 8 9 8 8 6 6 8 7 4 3 9 9 9 9 9 9 8 7 8 -- 7 Chickweed 9 9 8 9 6 5 6 5 9 3 5 9 9 10 9 8 9 9 2 0 2 4 Cocklebur -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- 7 8 9 9 Corn 9 9 9 7 9 9 8 9 9 7 4 9 9 10 9 3 9 9 8 9 9 9 Cotton 9 9 9 9 10 8 8 9 9 9 0 9 9 9 9 9 9 9 9 9 9 9 Crabgrass 8 6 8 8 8 3 1 1 1 0 0 9 9 9 8 7 9 6 6 2 6 3 Giant foxtail 9 9 9 8 9 5 5 7 8 3 5 9 9 10 9 8 9 9 9 6 9 8 Lambsquarters 10 9 10 9 10 7 7 10 10 7 4 -- -- 10 10 10 10 7 10 9 9 10 Morningglory 9 9 10 8 8 8 8 5 9 4 3 9 9 10 10 9 9 7 9 8 10 10 Nutsedge 7 3 8 3 5 2 0 -- 1 0 0 5 9 9 5 0 -- 5 8 9 9 9 Rape 2 9 9 10 9 2 7 8 9 5 0 9 10 9 9 9 9 5 9 7 10 10 Rice 9 9 9 8 9 5 8 9 9 9 4 10 9 9 9 8 9 9 9 9 10 9 Sorghum 9 9 9 9 9 9 9 9 9 6 4 9 9 9 9 9 9 9 9 8 9 10 Soybean 9 8 9 1 8 2 7 5 9 3 2 9 9 9 8 6 9 9 9 8 9 9 Sugar beet 9 9 9 9 9 7 8 9 9 6 3 9 9 9 9 8 9 7 7 7 9 8 Velvetleaf 8 9 9 9 8 6 8 8 9 3 0 9 9 10 9 9 9 9 9 9 8 9 Wheat 9 8 9 8 7 5 4 5 8 2 2 9 9 9 8 9 9 8 8 7 8 6 Wild buckwheat 9 8 9 9 9 3 7 8 9 7 0 9 9 7 9 9 7 7 8 7 -- 9 Wild oat 9 9 9 8 8 5 8 8 7 2 5 9 9 9 8 9 9 9 9 8 9 9
TABLE A - TEST A COMPOUND Rate (50 g/ha) 311 312 313 314 315 316 317 318 319 320 321 322 323 324 325 326 327 328 329 330 331 332 POSTEMERGENCE Barley 9 8 8 5 0 0 0 1 0 0 0 9 9 9 9 9 8 5 8 0 0 0 Barnyardgrass 9 9 6 6 0 0 0 0 0 0 0 9 9 9 9 7 9 2 4 0 0 0 Bedstraw 9 8 7 6 0 6 7 6 5 2 0 8 9 9 8 8 9 7 8 0 0 0 Blackgrass 9 9 9 6 0 3 2 3 0 0 0 9 9 9 9 9 9 6 9 0 0 0 Cheatgrass 8 7 7 5 0 0 1 5 2 0 0 9 9 9 9 9 9 9 9 0 0 0 Chickweed 2 3 3 5 0 2 0 0 0 0 0 9 10 9 9 7 10 1 4 0 0 0 Cocklebur 9 9 3 -- 0 7 8 9 9 8 0 9 10 10 7 2 10 0 6 0 0 0 Corn 9 8 4 0 0 0 0 6 6 0 0 9 9 9 9 9 9 9 9 0 0 0 Cotton 9 9 1 4 0 7 3 6 2 0 0 9 10 9 9 9 9 8 7 0 0 0 Crabgrass 3 3 0 0 0 0 0 0 0 0 0 9 9 9 7 4 5 0 7 0 0 0 Giant foxtail 8 9 6 2 0 0 0 3 0 0 0 9 9 9 9 4 9 8 9 0 0 0 Lambsquarters 10 -- 7 6 0 7 8 7 4 0 0 10 10 10 9 7 10 -- 7 -- 0 0 Morningglory 10 9 8 4 0 8 7 7 7 2 0 9 10 10 9 6 9 2 7 0 0 0 Nutsedge 9 9 0 0 0 0 0 0 0 0 0 9 9 9 3 -- 4 0 0 0 0 0 Rape 10 7 4 4 0 5 7 7 7 2 2 10 10 9 9 9 9 0 0 0 0 0 Rice 9 9 9 9 0 7 5 9 9 4 0 9 10 10 9 9 9 9 9 0 0 0 Sorghum 9 9 8 8 0 0 0 7 2 0 0 9 9 9 9 9 9 9 9 0 0 0 Soybean 9 8 8 6 0 0 0 5 2 0 0 9 9 9 9 9 9 7 9 0 0 0 Sugar beet 9 8 5 7 0 3 2 6 7 0 2 9 9 10 9 9 9 7 9 0 0 0 Velvetleaf 6 9 0 2 0 6 2 3 4 0 0 9 9 10 7 2 9 5 6 0 0 0 Wheat 8 5 5 3 0 0 0 3 0 0 0 9 9 9 9 9 8 7 9 0 0 0 Wild buckwheat 9 9 0 -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Wild oat 9 7 7 5 0 0 0 0 0 2 0 9 9 9 9 9 7 9 9 0 0 0 COMPOUND Rate (50 g/ha) 333 334 335 336 337 338 339 340 341 342 POSTEMERGENCE Barley 0 0 0 0 0 9 9 9 9 9 Barnyardgrass 0 0 0 0 0 10 10 9 9 10 Bedstraw 2 0 0 0 2 9 9 8 9 9 Blackgrass 0 0 0 0 0 9 9 9 9 10 Cheatgrass 0 0 0 0 0 9 9 9 9 9 Chickweed 0 3 2 0 2 10 10 7 2 9 Cocklebur 0 0 0 0 0 10 10 5 0 10 Corn 0 0 0 0 0 10 10 9 9 10 Cotton 0 0 0 0 0 9 9 5 3 10 Crabgrass 0 0 0 0 0 9 10 5 3 7 Giant foxtail 0 0 0 0 0 9 10 9 8 10 Lambsquarters 2 0 0 0 2 10 10 7 7 10 Morningglory 0 0 0 0 0 10 9 7 6 10 Nutsedge 0 0 0 4 0 9 9 3 1 10 Rape 2 4 0 0 1 9 9 8 8 9 Rice 4 0 0 0 0 9 9 9 9 10 Sorghum 0 0 0 0 0 9 9 9 9 10 Soybean 0 0 0 0 0 9 9 7 5 9 Sugar beet 1 2 0 0 1 10 9 7 5 9 Velvetleaf 0 0 0 0 0 10 9 3 0 10 Wheat 0 0 0 0 0 9 9 9 9 9 Wild buckwheat -- -- -- -- -- -- -- -- -- -- Wild oat 0 0 0 0 0 9 9 9 9 9 COMPOUND Rate (50 g/ha) 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 2 3 24 25 26 27 28 29 PREEMERGENCE Barley 4 7 7 3 9 2 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 8 8 8 9 6 Barnyardgrass 6 9 9 9 9 0 2 0 2 0 3 0 0 0 0 0 0 0 0 2 0 0 0 0 9 9 9 9 9 Bedstraw 4 9 9 9 9 8 0 6 0 7 0 0 0 0 0 2 0 3 0 9 2 2 0 0 9 9 9 9 8 Blackgrass 6 8 9 4 8 4 5 2 4 6 7 0 3 0 1 0 0 2 3 3 0 0 0 2 9 9 9 9 3 Cheatgrass 9 9 9 5 10 8 6 5 6 5 6 2 3 0 0 2 0 2 0 3 0 0 0 2 9 9 9 9 9 Chickweed 8 9 10 6 9 9 0 8 -- -- 9 0 8 5 2 0 5 8 -- 8 7 2 2 5 9 9 9 8 8 Cocklebur 0 0 0 0 8 10 0 4 0 0 2 0 0 -- 0 0 0 4 0 0 0 0 0 0 -- -- -- -- -- Corn 6 9 9 9 9 4 2 0 1 6 7 0 1 0 0 0 0 0 0 2 0 0 0 0 9 9 9 9 9 Cotton 5 8 7 7 8 7 0 0 4 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 5 7 7 6 7 Crabgrass 8 9 8 4 8 7 0 0 1 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 9 9 10 9 10 Giant foxtail 1 9 6 3 3 2 2 2 2 2 3 0 0 2 0 0 0 2 0 0 2 0 0 0 9 9 9 9 9 Lambsquarters 9 9 9 8 9 -- 0 6 6 6 9 6 6 -- 5 0 -- 3 6 3 0 0 0 0 9 10 10 10 9 Morningglory 0 5 8 5 9 5 2 2 0 2 0 0 0 0 0 0 0 0 0 1 0 0 0 0 6 9 8 9 9 Nutsedge 7 10 10 3 8 10 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 -- 9 8 8 9 10 Rape 8 6 9 9 9 9 0 0 3 5 2 0 6 0 0 1 0 2 0 0 0 0 0 0 8 9 9 9 9 Rice 9 9 8 9 10 9 2 0 3 0 3 0 6 0 0 0 0 0 2 2 0 0 0 4 10 9 9 10 10 Sorghum 9 9 7 7 9 9 3 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 3 0 9 9 8 9 9 Soybean 2 7 6 7 8 2 0 2 4 2 4 0 2 0 0 0 0 0 3 1 0 0 0 0 8 8 8 8 9 Sugar beet 7 8 9 9 10 9 0 3 4 4 7 2 2 4 0 0 0 0 2 0 0 0 0 2 8 9 9 9 9 Velvetleaf 4 8 5 6 9 0 2 1 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 3 5 6 9 8 Wheat 8 8 9 2 9 5 1 0 0 2 0 0 0 0 0 0 0 -- 0 0 0 0 0 0 9 9 8 3 7 Wild buckwheat 2 7 9 9 9 7 0 4 0 0 0 0 0 2 0 2 0 0 0 2 0 0 2 0 9 9 3 8 3 Wild oat 7 7 8 2 9 7 2 2 0 2 0 0 0 2 0 0 0 0 0 0 0 0 0 0 9 8 9 8 8 COMPOUND Rate (50 g/ha) 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 4 9 50 51 52 53 54 55 56 57 58 PREEMERGENCE Barley 2 2 0 0 2 8 8 0 2 0 0 0 0 0 0 0 0 0 0 0 3 7 2 8 2 2 4 4 2 Barnyardgrass 9 7 6 0 2 9 9 0 7 2 0 0 0 0 0 0 0 0 0 0 9 9 8 9 8 9 9 9 9 Bedstraw 8 6 6 7 0 7 8 2 3 0 0 0 0 0 0 0 -- 2 0 0 8 8 5 8 8 7 7 9 9 Blackgrass 7 8 0 5 7 7 8 0 3 2 2 2 1 0 0 2 1 3 2 0 8 8 9 9 4 2 8 9 9 Cheatgrass 8 7 8 4 9 9 9 0 7 5 4 3 3 3 0 2 3 3 0 4 8 8 8 9 6 2 8 9 8 Chickweed 9 7 6 8 8 9 9 0 8 6 6 7 9 2 0 3 0 7 2 3 -- 9 8 9 10 10 10 9 9 Cocklebur -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- 9 9 8 9 9 0 6 9 8 Corn 9 6 3 2 9 9 9 1 2 2 0 0 0 0 0 0 0 0 0 0 8 8 0 9 9 3 7 9 9 Cotton 9 0 0 1 3 5 8 0 0 0 0 0 0 0 0 0 0 0 0 1 8 9 1 9 9 2 9 8 8 Crabgrass 9 7 6 1 9 9 9 0 0 0 0 0 0 0 0 0 0 0 0 0 6 9 6 9 5 2 1 7 2 Giant foxtail 9 9 5 2 9 9 9 0 5 0 0 0 0 0 0 0 0 0 0 0 9 9 5 9 1 0 2 9 6 Lambsquarters 8 9 9 7 10 10 10 4 8 9 0 10 3 0 0 0 0 0 4 2 9 9 8 10 9 8 9 9 9 Morningglory 9 2 0 0 1 9 9 0 0 0 0 0 0 0 0 0 0 0 0 0 7 9 2 9 9 8 0 2 6 Nutsedge 9 5 0 0 0 8 2 0 0 0 0 0 0 -- 0 0 0 0 0 0 10 10 5 10 10 10 -- 8 -- Rape 9 0 0 4 3 4 8 0 3 0 2 2 2 2 0 0 0 0 0 0 9 9 9 9 9 8 9 9 9 Rice 10 8 7 4 7 9 10 0 8 5 4 8 3 0 0 0 0 2 0 3 9 10 9 9 9 9 8 8 9 Sorghum 9 6 2 2 2 9 9 0 2 1 0 0 0 0 0 0 0 0 0 0 7 6 3 9 3 1 7 9 4 Soybean 9 2 1 1 1 8 9 1 1 3 0 0 2 0 0 0 0 0 0 0 6 8 1 8 9 1 2 8 8 Sugar beet 9 4 7 6 8 9 9 2 9 2 1 2 3 2 0 2 0 2 0 2 9 9 9 9 9 9 9 9 9 Velvetleaf 9 1 1 0 1 2 9 0 0 0 0 0 0 0 0 0 0 0 0 0 8 9 5 9 0 4 5 8 7 Wheat 8 7 2 0 0 8 9 0 2 0 0 2 0 0 0 0 0 0 0 0 3 8 7 9 2 0 3 7 3 Wild buckwheat 8 2 0 0 0 3 2 0 2 0 2 0 3 0 0 0 0 0 0 0 1 7 6 8 9 0 7 9 9 Wild oat 9 8 2 3 8 9 9 0 2 2 0 0 2 0 0 0 0 2 0 0 4 8 8 9 8 0 8 8 5 COMPOUND Rate (50 g/ha) 59 60 61 62 63 64 65 66 67 68 69 70 71 72 73 74 75 76 77 7 8 79 80 81 82 83 84 85 86 87 PREEMERGENCE Barley 4 2 0 2 6 6 0 0 3 2 1 5 0 0 2 2 0 0 3 0 0 0 5 7 2 4 0 1 0 Barnyardgrass 5 6 4 9 9 9 6 0 8 7 7 1 0 0 0 6 0 1 4 9 0 0 5 9 9 8 3 9 3 Bedstraw 9 9 8 0 6 8 0 4 5 6 0 8 8 2 0 1 1 0 2 1 0 0 1 8 9 5 3 7 1 Blackgrass 7 6 5 4 8 9 4 1 5 6 2 3 3 0 0 5 0 2 5 7 3 0 9 9 9 7 2 9 3 Cheatgrass 8 7 6 7 8 8 7 5 7 8 7 6 0 0 7 8 0 2 8 9 1 0 9 9 9 7 2 9 8 Chickweed 10 10 9 5 9 9 3 0 9 9 8 8 7 5 5 7 0 0 5 7 2 0 7 9 9 7 0 7 1 Cocklebur 9 9 0 1 8 8 0 -- 8 8 0 9 0 0 0 -- 2 1 2 5 0 0 -- -- -- -- -- -- -- Corn 9 7 2 0 7 9 8 2 1 9 3 8 2 0 0 2 2 0 5 9 0 0 0 7 9 9 9 5 0 Cotton 9 9 5 0 7 8 1 0 4 8 0 8 7 0 1 2 0 2 0 1 0 0 7 5 8 3 0 5 0 Crabgrass 4 3 0 6 9 9 6 2 7 5 2 2 0 0 1 2 1 0 4 7 0 0 6 4 7 3 4 0 0 Giant foxtail 2 4 2 2 9 9 3 0 5 6 2 2 0 0 1 4 0 0 5 8 0 0 3 9 8 3 3 5 2 Lambsquarters 9 9 10 9 9 10 9 0 9 9 6 -- 8 7 6 9 0 0 8 7 0 0 9 10 10 10 9 10 8 Morningglory 9 9 3 0 2 8 3 0 0 7 2 9 0 0 0 5 1 2 3 5 0 0 7 7 9 7 3 9 1 Nutsedge -- 9 8 5 10 10 0 0 10 10 0 0 0 -- 0 0 0 0 4 10 -- -- 9 10 10 5 6 10 0 Rape 9 9 9 5 9 9 1 0 9 8 3 7 9 2 2 2 0 0 3 7 1 0 9 9 9 4 0 9 1 Rice 9 9 9 9 10 8 10 8 9 7 8 7 2 1 4 7 0 0 7 8 0 0 8 8 9 9 8 9 0 Sorghum 5 3 2 6 8 9 4 2 9 7 0 2 2 0 2 1 0 0 4 5 0 0 8 9 9 9 5 9 3 Soybean 9 8 0 1 8 9 3 3 0 8 0 7 4 0 5 7 1 3 7 6 0 0 2 6 9 7 4 9 1 Sugar beet 9 9 9 4 9 9 5 5 9 8 7 9 9 4 4 8 3 2 9 8 1 0 8 9 9 9 8 9 8 Velvetleaf 9 8 2 2 7 7 5 0 5 6 2 8 0 0 0 2 1 0 0 3 0 0 5 9 9 4 0 1 1 Wheat 2 4 0 5 7 7 8 0 7 2 1 2 0 0 0 0 0 0 4 2 0 0 8 7 7 8 5 1 0 Wild buckwheat 9 8 7 3 3 3 0 3 0 0 0 3 0 0 0 1 2 0 1 4 0 0 6 9 9 9 -- 7 -- Wild oat 8 8 0 5 6 6 6 0 6 4 2 2 0 0 2 3 0 0 3 3 0 0 7 6 3 7 1 2 COMPOUND Rate (50 g/ha) 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 PREEMERGENCE Barley 0 0 0 0 0 1 2 3 0 2 1 1 0 0 4 7 2 1 0 5 6 8 8 7 0 Barnyardgrass 9 9 4 2 9 5 7 5 3 3 4 1 2 0 3 6 2 0 0 9 7 9 9 8 8 Bedstraw 3 8 0 0 0 0 0 0 2 3 5 2 5 0 2 7 2 2 0 8 8 7 8 5 2 Blackgrass 6 7 7 2 8 2 5 2 3 6 8 7 4 2 6 8 5 2 2 7 9 9 9 7 7 Cheatgrass 9 8 7 5 8 7 0 0 5 6 6 4 0 0 8 8 2 3 3 9 9 9 9 8 7 Chickweed 7 8 8 8 0 9 8 -- 9 9 9 9 9 0 5 8 0 0 0 10 9 9 9 8 9 Cocklebur -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Corn 6 9 9 9 0 4 7 8 7 6 7 8 7 0 0 0 0 0 0 9 8 9 9 8 7 Cotton 5 5 2 0 0 6 5 3 7 9 3 7 5 0 -- 9 0 0 0 9 9 9 9 7 7 Crabgrass 2 3 0 0 0 7 5 2 2 6 5 0 0 0 1 3 1 0 0 8 8 9 9 7 8 Giant foxtail 5 3 0 0 0 5 7 0 1 2 7 0 0 0 3 3 0 0 0 8 3 8 9 6 2 Lambsquarters 9 9 9 9 9 9 6 9 9 -- 9 7 9 0 9 9 0 2 3 9 10 9 9 9 9 Morningglory 2 8 6 7 2 1 1 9 4 0 1 2 3 0 7 8 0 0 0 10 9 9 8 9 6 Nutsedge 8 10 10 0 0 0 6 0 4 5 0 0 3 0 0 0 10 0 -- 10 10 10 10 4 9 Rape 9 9 3 3 4 2 3 7 7 6 2 7 9 0 3 6 0 0 0 9 9 9 9 9 7 Rice 7 8 9 8 9 4 9 8 9 3 8 3 4 0 5 8 4 0 0 9 9 10 9 9 9 Sorghum 9 8 7 6 6 7 8 9 4 8 9 5 3 0 3 8 0 0 0 8 8 9 9 9 9 Soybean 5 7 5 3 0 2 5 7 7 1 3 4 7 0 0 1 0 0 0 9 8 8 8 8 5 Sugar beet 8 6 5 8 2 8 5 8 9 5 6 9 9 0 8 9 1 1 0 9 9 9 9 9 8 Velvetleaf 4 6 0 0 0 0 1 1 0 1 0 6 1 0 0 3 1 0 0 9 8 8 9 9 9 Wheat 0 0 2 3 0 3 6 0 0 3 6 0 0 0 8 8 2 2 0 6 6 9 7 5 0 Wild buckwheat 9 10 0 -- -- 0 5 8 0 3 5 3 5 0 2 7 5 2 1 5 8 3 3 2 5 Wild oat 0 2 5 0 0 1 2 1 2 3 5 6 0 0 4 3 0 0 0 7 7 7 7 2 5 COMPOUND Rate (50 g/ha) 113 114 115 116 117 118 119 120 121 122 123 124 125 126 127 128 129 130 131 132 133 134 PREEMERGENCE Barley 5 7 0 2 0 0 8 7 7 7 1 2 2 1 1 1 0 0 0 2 0 0 Barnyardgrass 9 9 9 9 7 7 10 9 9 9 1 4 0 5 0 0 2 6 3 2 0 0 Bedstraw 7 8 8 9 9 7 7 3 8 7 2 5 3 8 6 1 2 0 0 8 7 2 Blackgrass 7 7 8 5 3 3 8 7 9 6 5 6 5 7 4 3 0 5 2 3 6 3 Cheatgrass 8 9 8 8 7 6 9 8 9 9 7 7 7 6 3 2 2 7 7 4 3 2 Chickweed 4 8 7 7 8 3 10 9 10 9 8 9 -- 10 7 10 3 9 9 9 5 0 Cocklebur -- -- -- -- -- -- -- -- -- -- 3 3 2 5 3 0 2 5 7 8 6 0 Corn 9 9 9 9 6 5 9 9 10 9 0 5 0 0 0 0 0 2 5 8 2 0 Cotton 5 8 9 9 9 0 9 9 10 10 5 7 1 -- 4 3 2 6 0 5 3 3 Crabgrass 4 5 3 7 3 2 9 6 9 9 2 1 1 2 2 0 3 2 2 2 6 0 Giant foxtail 3 9 5 8 1 3 9 9 8 7 2 3 1 2 1 0 3 0 2 2 2 0 Lambsquarters 6 9 9 9 10 9 10 10 10 10 7 9 9 10 9 -- 9 9 7 9 9 5 Morningglory 5 9 9 9 9 6 9 9 9 10 2 2 2 8 3 0 1 2 3 7 6 0 Nutsedge 9 10 9 9 8 4 10 10 9 10 2 0 0 2 -- 0 0 9 9 9 0 0 Rape 7 8 9 9 9 7 9 9 9 9 9 9 9 9 5 9 5 8 8 7 5 5 Rice 8 9 9 9 9 8 10 9 10 10 7 5 2 8 5 3 2 2 0 7 8 0 Sorghum 8 9 9 8 6 6 9 9 9 9 0 0 0 6 3 0 0 5 2 4 6 2 Soybean 1 8 7 9 9 1 9 9 9 9 1 2 0 1 0 0 0 2 3 2 1 0 Sugar beet 5 8 7 9 9 8 9 9 9 9 8 8 9 9 9 9 6 6 6 9 8 4 Velvetleaf 2 9 9 9 9 1 9 9 9 8 6 8 5 8 0 0 4 8 7 8 0 3 Wheat 2 6 2 2 2 0 8 7 8 8 2 2 2 2 2 0 0 0 0 0 0 2 Wild buckwheat 0 3 5 7 5 2 7 4 7 5 2 7 6 8 3 0 2 5 7 4 7 3 Wild oat 5 7 4 7 5 2 7 6 7 7 7 4 4 5 2 0 2 3 3 3 2 3 COMPOUND Rate (50 g/ha) 135 136 137 138 139 140 141 142 143 144 145 146 147 148 149 150 151 152 165 166 167 168 PREEMERGENCE Barley 4 0 4 8 2 3 7 8 7 6 1 2 5 7 9 0 0 0 4 8 8 2 Barnyardgrass 8 5 7 9 3 8 3 9 9 2 1 8 5 6 7 0 0 7 7 7 7 8 Bedstraw 7 7 9 7 5 5 4 7 8 8 5 9 6 8 9 8 5 9 2 8 6 0 Blackgrass 7 6 8 9 8 8 6 10 8 7 7 7 9 8 9 5 5 8 5 8 8 3 Cheatgrass 8 8 9 9 9 8 8 10 10 8 8 9 9 9 9 9 9 8 7 8 9 6 Chickweed 8 8 9 9 5 9 5 9 7 10 0 8 9 9 -- 7 7 7 8 9 9 5 Cocklebur 0 0 2 5 2 1 7 9 9 5 2 9 5 9 7 2 2 0 3 3 2 -- Corn 6 3 6 7 0 4 3 9 9 9 8 9 0 5 5 8 6 3 3 8 7 2 Cotton 4 0 -- 8 0 2 5 7 8 8 2 4 2 6 6 2 1 3 0 8 2 0 Crabgrass 0 0 0 2 2 3 2 7 9 3 0 5 7 2 5 0 1 0 7 8 6 5 Giant foxtail 3 0 2 6 2 5 9 9 9 4 0 3 2 3 3 0 0 0 9 8 7 2 Lambsquarters 9 8 9 9 9 8 7 9 9 5 7 9 8 9 9 9 5 9 8 9 8 8 Morningglory 6 3 6 8 3 6 2 6 9 8 6 9 8 8 8 5 4 3 0 4 3 0 Nutsedge 0 0 0 0 0 2 9 9 10 2 0 10 5 9 10 0 0 8 7 10 0 0 Rape 0 5 4 0 1 2 7 9 9 9 3 9 8 9 9 3 0 7 8 9 8 8 Rice 7 1 7 9 5 6 9 9 10 10 8 9 10 8 10 9 9 10 9 8 9 9 Sorghum 9 5 6 9 2 6 8 8 9 8 3 7 5 6 6 3 2 5 9 9 9 5 Soybean 2 0 2 3 2 0 7 9 9 8 4 9 7 9 9 8 6 6 2 7 4 0 Sugar beet 9 8 8 9 8 8 7 9 9 9 3 9 7 9 9 8 7 7 7 9 8 3 Velvetleaf 0 6 3 2 4 3 7 9 9 6 0 9 5 7 9 2 0 0 1 6 2 1 Wheat 7 3 7 8 5 7 7 8 8 9 6 5 6 7 9 4 4 3 2 8 8 2 Wild buckwheat -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- 4 3 5 3 Wild oat 8 5 7 8 4 6 7 7 5 8 3 5 7 4 5 3 2 2 3 8 8 2
TABLE A - TEST A COMPOUND Rate (50 g/ha) 169 170 171 172 173 174 175 176 177 178 179 180 181 182 183 184 185 186 187 188 189 190 PREEMERGENCE Barley 0 0 0 2 3 0 0 0 0 0 0 0 0 8 6 5 3 7 2 0 0 0 Barnyardgrass 3 9 5 3 6 7 9 0 0 0 0 9 9 8 9 3 9 9 6 1 1 2 Bedstraw 6 6 0 2 5 1 0 0 0 2 0 2 2 9 8 2 7 8 6 0 2 5 Blackgrass 2 9 -- 7 8 2 7 0 3 3 2 4 5 9 9 9 9 9 9 6 5 7 Cheatgrass 0 8 -- 8 8 7 8 5 2 2 0 7 7 9 10 9 9 10 10 7 7 7 Chickweed 7 8 0 7 8 2 4 0 3 4 0 4 9 9 9 -- 8 9 8 0 -- 3 Cocklebur -- 5 -- 0 2 0 2 0 0 0 0 0 0 7 8 7 8 8 8 2 0 0 Corn 0 5 1 5 8 6 6 0 0 0 0 7 8 9 9 9 9 9 9 3 9 4 Cotton 4 2 0 5 8 2 0 0 0 0 0 0 0 8 3 8 9 9 6 0 0 3 Crabgrass 5 5 7 9 8 6 9 2 0 0 0 9 9 9 10 9 9 10 9 8 5 6 Giant foxtail 7 8 8 9 8 5 7 6 0 4 0 9 9 9 10 9 9 9 9 8 7 6 Lambsquarters 7 9 7 9 9 5 9 -- 0 3 2 3 5 8 9 9 9 9 5 4 3 5 Morningglory 2 5 0 6 3 6 4 0 0 1 0 0 2 6 6 6 9 7 4 0 4 3 Nutsedge 0 4 0 0 8 0 0 0 0 0 0 0 9 7 10 8 10 7 5 7 0 0 Rape 9 9 0 4 8 3 0 0 0 0 0 0 2 7 8 5 9 9 6 0 0 0 Rice 9 10 3 7 9 7 9 0 0 0 0 7 9 9 9 8 10 10 9 8 9 9 Sorghum 0 7 1 7 8 7 9 0 0 0 0 9 9 8 9 9 9 9 8 0 1 1 Soybean 3 4 0 5 8 4 3 0 0 0 0 0 1 9 9 9 8 9 9 2 6 2 Sugar beet 9 9 6 9 8 5 6 2 0 2 2 3 7 9 7 7 7 8 7 3 3 7 Velvetleaf 3 9 0 5 7 2 0 0 0 0 0 0 0 7 8 7 6 7 5 0 2 2 Wheat 2 4 0 7 7 0 6 0 0 2 0 7 6 7 7 6 0 8 8 0 2 6 Wild buckwheat 3 2 0 -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Wild oat 2 3 0 4 3 0 4 0 0 0 3 1 2 8 7 7 2 7 7 4 6 5 COMPOUND Rate (50 g/ha) 191 192 203 204 205 206 207 208 209 210 211 212 213 214 215 216 217 218 219 220 221 222 PREEMERGENCE Barley 0 0 8 9 8 9 7 8 2 0 2 7 5 3 1 2 3 1 0 0 0 0 Barnyardgrass 1 2 5 9 9 9 9 9 0 6 9 8 8 6 9 4 3 7 3 0 0 0 Bedstraw 5 0 0 8 9 9 8 9 4 5 8 8 8 9 6 0 1 8 2 0 0 1 Blackgrass 7 7 8 8 9 8 9 8 2 2 8 8 7 6 5 6 6 7 6 0 3 0 Cheatgrass 7 7 9 9 9 9 8 9 8 8 9 9 9 9 8 6 8 9 8 4 0 2 Chickweed 2 6 9 9 9 9 10 9 0 7 9 10 10 9 9 8 7 9 9 2 2 5 Cocklebur 0 0 -- 8 10 10 9 9 8 -- 8 -- -- -- 0 0 0 0 0 -- 0 -- Corn 3 7 9 9 9 9 9 9 0 8 9 9 9 9 7 8 3 2 0 5 0 0 Cotton 0 0 7 4 8 7 8 7 0 0 8 8 8 9 5 0 0 -- 0 0 0 0 Crabgrass 6 9 9 9 9 9 9 9 3 8 9 7 9 4 5 3 6 3 2 0 2 3 Giant foxtail 6 9 8 9 9 9 9 9 3 6 9 9 8 2 3 5 5 2 0 0 2 0 Lambsquarters 0 5 9 9 10 9 8 9 5 8 9 9 9 9 8 7 9 9 9 6 -- 9 Morningglory 3 3 7 9 9 9 4 9 2 1 3 2 3 9 2 0 3 2 1 0 1 0 Nutsedge 0 0 6 10 10 9 5 10 0 0 3 8 8 9 2 0 9 0 0 0 0 0 Rape 2 0 8 8 9 7 4 9 0 3 9 9 8 8 8 1 9 7 1 0 1 0 Rice 0 7 9 9 9 9 10 10 5 6 9 9 9 9 6 6 9 7 6 0 3 6 Sorghum 0 4 9 8 9 8 8 9 0 5 9 9 9 8 8 3 3 2 0 0 0 0 Soybean 2 8 9 8 8 8 8 8 0 3 7 7 9 8 2 2 4 4 0 1 0 0 Sugar beet 4 5 8 9 9 9 9 9 1 8 6 7 9 9 7 4 2 4 3 1 1 1 Velvetleaf 2 2 7 6 9 8 5 8 0 4 7 4 9 0 6 0 6 7 2 0 0 0 Wheat 0 2 7 9 9 9 8 8 0 7 9 8 6 1 3 6 8 8 0 0 0 0 Wild buckwheat -- -- 5 8 8 8 3 8 0 3 1 7 8 8 3 1 5 2 0 3 3 0 Wild oat 2 7 8 9 8 8 7 8 2 7 9 8 8 8 3 6 7 3 2 0 0 1 COMPOUND Rate (50 g/ha) 223 224 225 226 227 228 229 230 231 232 233 234 235 236 237 238 239 240 241 242 243 244 PREEMERGENCE Barley 1 1 0 0 0 5 5 2 4 5 0 0 0 0 0 0 0 8 8 8 8 8 Barnyardgrass 7 0 0 0 0 2 5 1 5 1 3 0 0 2 0 0 0 9 9 9 9 9 Bedstraw 7 6 0 0 0 3 2 3 3 0 3 2 0 0 0 4 3 7 7 7 8 8 Blackgrass 2 5 3 0 0 3 8 7 4 3 4 3 0 0 0 3 0 7 9 9 9 7 Cheatgrass 7 8 7 0 2 7 10 8 9 8 8 0 0 0 0 0 0 8 9 9 9 8 Chickweed 9 8 5 4 9 0 9 2 2 0 0 0 0 0 0 0 0 9 9 9 9 9 Cocklebur -- 0 0 0 -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Corn 2 8 0 0 0 2 8 8 4 3 1 0 2 2 0 0 2 9 9 9 9 9 Cotton 0 2 0 0 0 2 4 5 2 2 2 0 0 2 0 0 0 8 7 7 9 10 Crabgrass 0 3 0 0 0 2 5 3 6 6 2 0 0 2 0 0 0 9 9 9 9 9 Giant foxtail 5 7 0 0 0 3 7 1 5 2 0 0 0 2 0 0 0 9 9 9 9 9 Lambsquarters -- 8 -- -- 7 9 9 7 4 5 0 7 0 0 0 2 2 9 9 9 9 9 Morningglory 3 2 0 0 0 5 6 6 7 5 -- 0 0 1 0 0 0 7 6 8 8 8 Nutsedge 0 0 0 0 0 2 5 6 5 0 6 0 0 4 0 0 -- 10 9 9 10 10 Rape 7 8 2 0 0 0 3 3 0 3 2 0 0 0 0 0 0 9 9 9 9 9 Rice 5 4 5 4 0 1 8 7 8 8 9 0 0 1 0 2 2 9 9 9 10 9 Sorghum 6 1 2 2 0 3 7 7 8 6 2 0 0 2 0 0 0 9 9 9 9 8 Soybean 3 5 3 2 0 4 7 2 5 4 2 0 0 0 0 0 0 9 9 9 8 9 Sugar beet 6 7 0 1 2 2 4 2 3 2 2 2 0 0 0 0 0 9 9 9 9 9 Velvetleaf 2 8 0 0 0 4 6 6 6 0 0 0 0 0 0 0 0 8 9 9 9 7 Wheat 0 2 0 0 0 3 6 6 7 7 3 0 0 0 0 0 0 8 7 7 8 8 Wild buckwheat 3 6 0 3 0 0 0 2 2 0 2 2 -- 0 3 2 3 7 9 7 5 7 Wild oat 0 2 3 0 0 4 7 7 5 6 1 0 0 0 0 0 0 7 7 7 7 7 COMPOUND Rate (50 g/ha) 245 246 247 248 249 250 251 252 253 254 255 256 257 258 259 260 261 262 263 264 265 266 PREEMERGENCE Barley 8 3 2 0 0 0 5 1 5 0 0 8 5 8 5 0 8 0 0 0 2 0 Barnyardgrass 9 4 6 1 0 1 8 3 6 2 3 4 8 9 9 8 9 1 0 2 2 5 Bedstraw 8 2 3 5 2 0 8 5 8 7 7 7 7 7 3 2 9 3 2 3 3 3 Blackgrass 9 8 7 3 4 3 8 7 6 5 2 8 8 8 6 8 8 3 0 2 8 7 Cheatgrass 9 5 8 4 2 7 8 7 8 8 6 8 8 9 8 8 8 5 0 8 8 7 Chickweed 9 9 9 7 9 9 9 6 9 9 5 5 8 9 7 3 9 5 3 2 0 3 Cocklebur -- -- -- -- -- 0 2 -- 6 5 0 1 0 2 1 5 7 0 0 2 0 2 Corn 9 4 8 5 3 2 8 9 9 8 5 9 9 9 9 9 9 2 0 4 8 6 Cotton 8 0 0 3 0 1 5 4 9 8 2 7 6 8 9 2 8 0 2 0 6 7 Crabgrass 9 7 9 7 2 2 8 4 3 4 0 9 7 8 8 7 8 0 0 2 4 0 Giant foxtail 9 4 9 4 3 1 8 7 3 2 0 6 8 9 7 8 8 1 0 2 5 5 Lambsquarters 9 9 7 9 9 8 9 7 10 9 6 9 9 9 9 -- 8 7 3 5 9 5 Morningglory 8 0 3 2 2 1 1 3 9 8 1 8 8 8 3 1 8 0 0 5 3 4 Nutsedge 10 8 6 -- -- 0 0 2 8 0 0 9 7 8 0 0 8 0 0 0 0 0 Rape 9 2 5 7 8 3 8 7 8 8 6 9 7 8 6 4 9 0 0 5 7 7 Rice 10 4 8 2 0 1 7 8 8 8 0 9 9 9 -- 9 9 0 2 0 6 8 Sorghum 9 2 4 3 0 3 8 8 9 7 5 9 9 9 9 8 9 1 2 5 7 9 Soybean 8 0 2 5 0 1 5 7 7 8 1 7 7 8 8 5 4 0 2 2 7 3 Sugar beet 9 7 7 8 9 1 8 3 8 7 5 6 8 7 6 2 5 2 0 2 3 2 Velvetleaf 6 3 3 2 2 2 8 6 9 0 2 7 5 8 1 1 2 0 0 7 7 4 Wheat 7 5 5 0 0 0 6 6 0 2 0 7 7 8 7 6 7 0 0 5 2 2 Wild buckwheat 7 7 5 5 5 0 -- 3 3 3 2 3 3 3 2 2 4 0 2 3 3 0 Wild oat 7 2 6 0 0 1 5 3 4 5 2 7 8 8 7 6 7 2 3 7 4 3 COMPOUND Rate (50 g/ha) 267 268 269 270 271 272 273 274 275 276 277 278 279 280 281 282 283 284 285 286 287 288 PREEMERGENCE Barley 4 2 0 9 7 8 0 2 9 0 0 0 0 0 0 1 9 8 2 4 9 8 Barnyardgrass 4 1 0 1 4 8 2 1 9 0 0 0 0 1 2 2 9 9 9 9 9 9 Bedstraw 3 6 2 3 3 3 0 0 0 0 0 0 2 0 0 2 8 7 9 9 7 8 Blackgrass 8 8 4 9 9 7 7 2 9 6 1 2 1 0 2 5 8 8 6 8 5 8 Cheatgrass 9 9 8 9 9 9 8 8 9 8 1 0 0 3 2 4 9 9 9 9 9 9 Chickweed -- 4 3 6 9 9 3 0 9 0 0 0 0 0 0 7 8 9 9 10 10 9 Cocklebur 6 1 0 1 1 2 2 0 7 0 0 0 4 0 0 0 8 7 8 7 7 7 Corn 7 6 1 9 8 8 2 2 9 0 0 0 0 2 7 2 9 9 6 6 9 9 Cotton 8 6 0 8 8 5 2 4 9 0 -- 0 0 0 0 0 9 9 9 9 9 8 Crabgrass 2 2 0 9 9 9 4 0 9 2 0 0 0 0 0 0 9 9 9 9 9 9 Giant foxtail 3 2 0 2 8 9 2 0 9 1 0 0 2 1 0 0 9 9 10 9 9 8 Lambsquarters 9 8 -- 9 9 10 0 0 9 0 0 0 0 5 -- 9 -- 9 9 -- 9 9 Morningglory 8 9 0 5 7 2 2 0 8 0 0 0 0 2 3 0 9 7 7 9 9 9 Nutsedge 5 0 0 10 9 6 0 0 9 0 0 0 0 0 0 0 9 6 4 5 9 9 Rape 5 8 3 8 8 5 1 1 8 1 0 0 2 0 0 4 9 9 9 9 9 9 Rice 8 8 6 9 9 9 9 8 9 0 0 0 0 0 0 1 9 7 7 8 9 8 Sorghum 8 8 4 9 8 8 4 3 9 0 0 0 0 2 0 0 9 8 9 8 8 9 Soybean 7 6 0 6 7 5 0 1 6 0 0 0 0 1 0 2 9 8 6 7 7 4 Sugar beet 7 8 1 9 9 7 1 1 9 2 0 0 2 0 0 5 9 9 9 9 9 9 Velvetleaf 7 0 0 1 1 0 1 0 1 0 0 0 0 0 0 0 8 8 9 9 5 9 Wheat 5 2 0 7 8 8 4 2 8 2 0 0 0 0 0 0 8 8 3 7 8 6 Wild buckwheat 5 5 2 -- 8 5 2 0 9 -- -- -- -- -- -- -- 5 5 7 3 2 6 Wild oat 7 8 2 8 8 8 3 2 8 2 0 0 0 0 0 2 8 7 3 8 6 6 COMPOUND Rate (50 g/ha) 289 290 291 292 293 294 295 296 297 298 299 300 301 302 303 304 305 306 307 308 309 310 PREEMERGENCE Barley 2 2 4 0 1 0 0 0 0 0 0 2 3 7 0 0 7 0 1 0 0 0 Barnyardgrass 6 2 9 0 5 0 0 0 0 0 0 9 6 9 2 0 8 6 1 1 0 0 Bedstraw 9 1 4 0 2 2 0 2 0 3 0 0 0 2 0 3 0 0 2 2 0 2 Blackgrass 8 6 8 2 6 0 7 3 3 3 4 8 7 7 5 0 7 4 7 5 5 1 Cheatgrass 9 6 9 0 7 0 2 5 0 2 2 8 8 8 2 0 9 7 7 2 3 0 Chickweed 9 7 8 1 5 8 8 8 7 2 0 7 7 9 0 3 9 3 0 1 3 3 Cocklebur 7 -- 0 0 0 0 0 0 0 0 0 -- -- -- -- -- -- -- 0 3 3 6 Corn 9 2 8 0 2 0 0 0 0 0 0 9 8 9 1 2 9 8 5 4 0 0 Cotton 2 0 2 0 1 0 0 0 0 0 0 5 6 9 0 0 5 1 0 2 0 3 Crabgrass 9 7 9 2 2 0 6 0 0 0 0 7 9 9 7 0 9 6 2 4 0 1 Giant foxtail 8 4 9 2 7 0 1 0 0 0 0 9 8 9 4 2 9 3 6 2 0 2 Lambsquarters 9 8 9 3 8 2 7 9 10 5 4 9 10 9 5 0 10 8 7 5 9 3 Morningglory 2 0 2 0 0 0 0 0 0 0 0 0 7 8 2 1 8 1 2 2 1 4 Nutsedge 10 3 8 0 0 0 0 0 0 0 0 0 8 9 0 0 9 0 9 0 8 0 Rape 2 6 9 2 2 0 3 3 2 2 0 3 8 7 0 0 2 0 7 8 5 7 Rice 7 0 7 0 4 0 0 0 0 0 0 8 8 9 0 0 9 7 9 0 2 0 Sorghum 9 0 8 0 3 0 0 0 0 0 0 8 8 9 0 2 9 5 8 0 0 0 Soybean 3 1 6 0 1 0 3 0 0 0 0 2 7 8 2 0 5 1 2 3 2 7 Sugar beet 9 2 8 3 4 2 2 2 1 1 2 9 9 9 0 0 6 3 3 5 5 7 Velvetleaf 0 0 1 0 0 0 0 0 0 0 0 0 3 7 2 1 2 0 6 7 6 6 Wheat 5 4 6 0 2 0 0 0 0 0 0 6 7 8 2 0 7 2 0 0 0 0 Wild buckwheat 3 5 8 0 2 0 3 0 0 0 3 0 0 4 2 0 0 0 -- -- -- -- Wild oat 2 4 5 0 1 3 2 2 0 0 0 6 6 8 0 0 7 4 3 2 0 0 COMPOUND Rate (50 g/ha) 311 312 313 314 315 316 317 318 319 320 321 322 323 324 325 326 327 328 329 330 331 332 PREEMERGENCE Barley 0 0 0 0 0 0 0 0 0 0 0 8 9 8 2 0 5 0 2 0 0 0 Barnyardgrass 4 0 0 0 0 0 0 0 0 0 0 2 4 7 2 0 9 2 2 0 0 0 Bedstraw 0 3 2 0 0 2 4 0 1 0 0 9 9 9 1 5 8 0 3 0 0 0 Blackgrass 3 7 1 2 0 0 0 0 0 0 0 8 9 9 7 6 9 3 7 0 0 0 Cheatgrass 0 5 0 2 0 0 0 0 0 0 0 9 9 9 8 7 9 7 9 0 0 0 Chickweed -- 0 0 0 0 5 0 0 0 0 0 9 9 9 8 7 9 5 7 -- -- 0 Cocklebur 3 5 3 0 0 0 0 2 2 0 0 5 2 7 0 2 2 0 1 0 0 0 Corn 0 4 0 2 0 0 0 0 0 0 0 9 9 9 9 2 9 2 8 0 0 0 Cotton 6 5 4 6 0 0 0 0 0 0 0 8 9 9 5 0 8 4 3 0 0 0 Crabgrass 2 2 4 0 0 0 0 0 0 0 0 8 9 9 5 0 9 5 4 0 0 0 Giant foxtail 4 5 4 0 0 0 0 0 0 0 0 8 9 9 2 0 9 2 2 0 0 0 Lambsquarters 9 9 5 10 0 3 2 3 0 0 0 9 9 9 8 -- 9 5 7 0 0 0 Morningglory 5 3 0 0 0 0 0 2 0 0 0 3 8 8 3 1 9 1 3 0 0 0 Nutsedge 2 3 0 0 0 0 0 0 0 0 0 8 9 9 3 0 8 0 0 0 0 0 Rape 5 7 0 0 0 0 0 0 0 0 0 9 9 9 2 2 9 0 0 0 0 0 Rice 2 0 0 0 0 0 0 0 0 0 0 9 9 9 10 8 9 5 7 0 0 0 Sorghum 2 0 0 0 0 0 0 0 0 0 0 9 9 9 7 0 9 3 4 0 0 0 Soybean 4 3 0 0 0 0 0 0 0 0 0 9 9 9 5 2 8 1 7 0 0 0 Sugar beet 7 6 0 0 0 0 0 0 0 0 0 9 9 9 7 8 9 2 2 0 0 0 Velvetleaf 3 6 0 0 0 0 0 0 1 0 0 7 8 9 1 0 8 0 0 0 0 0 Wheat 0 2 0 0 0 0 0 0 0 0 0 8 9 9 8 0 6 0 2 0 0 0 Wild buckwheat -- -- -- -- -- -- -- 0 -- -- 0 -- -- -- -- -- -- -- -- -- -- -- Wild oat 3 2 0 0 0 0 0 0 0 0 0 8 9 9 8 4 6 2 8 0 0 0
TABLE A - TEST A COMPOUND Rate (50 g/ha) 333 334 335 336 337 338 339 340 341 342 PREEMERGENCE Barley 0 0 0 0 0 8 9 2 2 7 Barnyardgrass 0 0 0 0 0 7 8 1 1 7 Bedstraw 0 2 0 0 0 5 1 0 0 2 Blackgrass 0 0 0 0 0 7 7 7 4 6 Cheatgrass 0 0 0 0 0 9 9 9 6 8 Chickweed 0 0 -- 0 0 9 9 -- 0 10 Cocklebur 0 0 0 0 0 6 7 2 0 6 Corn 0 0 0 0 0 9 9 3 6 9 Cotton 0 0 0 0 0 7 8 1 0 5 Crabgrass 0 0 0 0 0 9 9 3 4 9 Giant foxtail 0 0 0 0 0 9 9 5 3 9 Lambsquarters 2 2 0 0 0 10 9 0 0 10 Morningglory 0 0 0 0 0 7 6 3 0 9 Nutsedge 0 0 0 0 0 7 10 0 4 9 Rape 0 0 0 0 0 9 9 2 2 9 Rice 0 0 0 0 0 9 10 9 7 10 Sorghum 0 0 0 0 0 8 9 2 0 9 Soybean 0 0 0 0 0 9 9 2 0 6 Sugar beet 0 0 0 0 0 9 9 1 3 10 Velvetleaf 0 0 0 0 0 5 7 0 0 6 Wheat 0 0 0 0 0 8 9 8 3 7 Wild buckwheat -- -- -- -- -- -- -- -- -- -- Wild oat 0 0 0 0 0 8 7 8 2 5 COMPOUND Rate (10 g/ha) 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 2 3 24 25 26 27 28 29 POSTEMERGENCE Barley 8 7 6 5 7 8 7 8 7 7 8 7 8 4 2 3 3 2 4 0 0 0 0 2 8 8 8 8 9 Barnyardgrass 9 9 8 9 9 7 6 8 4 7 6 6 7 7 1 0 0 2 5 2 0 0 8 6 8 9 9 9 9 Bedstraw 8 8 9 8 9 9 2 8 2 3 3 3 5 3 2 0 0 0 2 5 3 2 2 5 7 5 8 7 8 Blackgrass 7 8 9 2 9 6 6 3 3 8 9 7 8 5 3 4 2 2 3 0 2 3 2 2 9 9 9 9 7 Cheatgrass 8 8 9 4 8 8 8 8 3 7 8 6 7 2 3 4 3 2 3 2 2 0 3 2 9 9 9 8 8 Chickweed 8 7 8 7 8 9 1 9 5 -- -- -- -- 9 4 -- -- 9 -- 3 6 3 7 10 9 7 9 6 -- Cocklebur 3 5 5 0 2 2 0 3 9 9 6 2 7 0 0 3 4 3 3 2 0 0 7 0 -- -- -- -- -- Corn 9 9 9 9 9 9 9 9 9 9 9 9 10 9 7 4 1 8 9 7 3 1 9 9 9 9 9 9 10 Cotton 9 9 9 9 9 9 9 9 2 6 8 2 7 6 0 0 0 3 0 0 0 0 1 2 8 8 9 9 9 Crabgrass 9 7 9 0 2 2 2 4 -- -- -- -- -- -- -- -- -- -- -- 2 0 0 2 6 5 2 8 4 8 Giant foxtail 8 9 7 3 7 5 7 4 7 7 9 8 6 7 4 0 0 5 7 3 2 2 7 6 9 8 9 8 9 Lambsquarters 9 9 9 8 8 9 8 9 9 8 8 9 8 7 3 7 5 4 4 5 5 3 8 3 10 10 8 8 10 Morningglory 9 9 9 9 9 8 8 9 5 8 9 0 6 8 5 2 1 6 7 2 1 0 1 4 9 9 10 9 10 Nutsedge 8 8 9 7 9 5 3 0 5 -- 5 2 2 3 0 0 0 0 0 0 2 0 2 2 9 7 9 7 7 Rape 5 7 8 7 9 9 0 0 4 6 8 6 9 9 0 2 0 0 7 6 7 5 8 9 7 7 8 9 9 Rice 9 9 9 9 9 9 9 9 9 9 9 9 10 9 8 3 2 9 9 7 7 3 9 9 9 9 9 9 9 Sorghum 9 9 9 9 9 9 9 7 9 9 7 9 9 9 5 2 2 7 9 5 4 0 9 8 9 9 9 9 9 Soybean 9 9 8 6 9 9 3 8 6 6 9 5 9 8 1 1 2 3 3 1 1 0 5 4 8 8 9 9 9 Sugar beet 6 8 8 5 9 9 2 9 6 7 8 3 7 4 0 2 2 0 0 7 7 3 8 8 9 8 9 9 9 Velvetleaf 9 9 7 7 10 3 2 8 2 2 6 0 7 8 0 0 0 3 2 2 0 0 6 2 8 9 9 8 9 Wheat 7 7 7 3 7 7 7 8 6 7 9 6 9 6 1 2 0 3 4 2 2 2 3 3 8 9 8 8 9 Wild buckwheat 9 8 8 7 8 9 1 5 4 2 9 2 5 3 0 0 0 0 0 3 7 2 0 5 9 4 8 8 9 Wild oat 8 9 9 3 8 8 8 2 7 8 9 6 6 3 0 0 0 2 1 1 0 0 2 5 9 9 9 8 10 COMPOUND Rate (10 g/ha) 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 4 9 50 51 52 53 54 55 56 57 58 POSTEMERGENCE Barley 9 8 7 7 7 7 8 2 5 2 0 4 2 3 0 0 2 3 0 2 4 5 8 8 2 2 6 7 4 Barnyardgrass 9 7 5 3 3 9 9 0 1 1 0 7 2 0 0 0 0 0 0 2 9 9 9 9 7 7 8 8 8 Bedstraw 8 4 6 4 3 6 7 2 3 2 2 3 2 0 2 0 0 3 0 3 7 9 -- 6 7 5 4 7 7 Blackgrass 8 8 4 2 7 8 9 0 0 0 0 2 3 2 3 2 0 0 0 0 9 8 -- 8 2 4 4 8 5 Cheatgrass 9 7 7 6 8 5 5 0 0 2 0 2 3 0 3 0 0 2 0 2 9 7 -- 7 3 3 5 7 6 Chickweed 9 4 -- 8 7 4 9 0 6 8 0 9 9 3 5 0 0 0 0 9 9 9 4 9 10 7 0 7 5 Cocklebur -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- 9 10 9 10 9 1 10 9 9 Corn 10 9 3 2 9 8 9 5 7 3 2 9 2 0 1 0 0 5 0 7 8 9 4 8 8 3 8 9 9 Cotton 9 2 3 0 5 9 9 0 0 0 0 1 5 0 0 0 0 0 0 0 9 9 9 9 9 8 9 9 9 Crabgrass 7 2 0 0 5 4 6 0 0 0 0 0 0 0 0 0 0 0 0 0 0 5 4 6 0 0 0 3 0 Giant foxtail 9 8 6 4 8 7 9 0 1 0 0 1 0 0 0 0 0 0 0 0 8 8 7 9 2 0 3 8 6 Lambsquarters 9 -- 7 8 5 9 9 3 3 7 7 9 -- 0 3 7 7 0 3 3 9 10 6 8 9 5 2 8 -- Morningglory 10 8 8 8 9 9 9 4 5 1 2 6 2 0 5 0 0 0 7 7 9 10 2 9 10 9 0 3 9 Nutsedge 5 -- 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 5 9 9 4 9 8 -- 9 9 9 Rape 10 2 2 5 7 0 9 6 5 7 6 9 8 2 0 0 4 4 0 6 9 9 7 9 9 8 9 8 9 Rice 9 9 9 7 9 9 9 2 2 0 0 9 9 0 0 0 0 2 0 0 9 9 9 9 9 8 8 9 8 Sorghum 10 9 4 3 7 9 9 0 1 0 0 5 1 0 0 0 0 1 0 0 8 9 9 9 7 3 7 9 8 Soybean 9 4 9 2 4 5 9 1 2 0 1 9 4 0 1 0 0 1 3 3 9 9 7 9 9 6 8 9 9 Sugar beet 10 7 5 6 8 7 9 7 8 8 8 9 8 2 7 6 7 0 4 9 8 10 3 8 9 7 7 7 8 Velvetleaf 9 3 1 1 2 8 9 3 5 5 0 3 2 0 0 0 0 0 0 2 9 10 9 9 5 8 9 8 9 Wheat 8 7 5 4 7 8 8 0 3 0 0 3 3 0 1 0 0 1 0 1 4 7 8 7 0 0 3 5 2 Wild buckwheat 8 0 0 2 2 2 5 5 4 5 7 8 7 0 0 0 0 3 2 2 5 10 -- 4 8 6 3 -- 4 Wild oat 10 8 7 7 9 9 9 0 2 0 0 4 2 0 1 0 0 1 0 0 5 9 8 7 2 0 6 4 COMPOUND Rate (10 g/ha) 59 60 61 62 63 64 65 66 67 68 69 70 71 72 73 74 75 76 77 7 8 79 80 81 82 83 84 85 86 87 POSTEMERGENCE Barley 4 2 0 7 7 5 4 3 1 9 0 5 0 0 3 3 0 0 4 3 2 0 7 7 7 6 3 2 2 Barnyardgrass 6 3 1 8 9 9 7 3 8 9 3 9 0 0 5 7 0 0 6 9 0 0 8 9 9 3 0 8 2 Bedstraw 8 8 -- 2 8 7 4 7 5 3 7 7 6 0 5 7 4 5 4 7 0 0 3 6 9 7 7 7 0 Blackgrass 5 5 0 7 9 9 8 4 3 1 0 2 0 0 2 4 5 0 5 8 5 0 9 9 9 9 8 9 4 Cheatgrass 7 7 -- 9 10 9 6 3 6 7 7 0 0 0 8 8 0 0 8 9 0 0 9 9 9 6 4 8 4 Chickweed 10 9 2 0 6 8 5 0 4 -- -- -- -- -- 5 7 8 3 -- 9 0 0 4 9 10 9 3 3 2 Cocklebur 10 10 9 5 9 9 7 7 9 9 6 9 9 2 -- 9 9 7 9 9 0 -- -- -- -- -- -- -- -- Corn 8 5 0 0 7 9 9 7 0 9 2 9 7 0 3 7 6 2 0 7 1 1 0 1 5 7 7 0 0 Cotton 10 9 9 7 9 9 6 4 7 9 6 9 9 2 6 9 5 5 7 9 2 0 8 9 9 8 7 8 6 Crabgrass 1 0 0 3 8 3 2 0 0 3 0 1 0 0 0 1 0 0 1 3 0 0 1 5 5 4 3 2 Giant foxtail 2 0 0 6 9 8 7 0 4 4 3 3 2 0 7 9 5 0 7 9 3 0 6 9 7 4 0 4 0 Lambsquarters 9 9 3 9 10 9 7 5 9 8 9 10 7 7 8 9 9 2 9 9 5 0 9 9 -- 9 9 8 1 Morningglory 9 10 8 7 9 10 8 6 9 10 9 9 10 2 9 9 0 1 9 9 2 0 9 9 9 9 8 9 9 Nutsedge 9 8 9 6 8 9 0 0 7 -- -- 0 0 5 0 9 -- 0 -- 5 0 0 0 -- -- 0 0 -- Rape 9 9 9 9 9 9 7 5 6 8 8 9 8 5 9 8 8 8 9 9 7 0 9 9 9 9 5 8 8 Rice 9 9 6 9 8 9 9 9 4 8 4 8 5 0 7 8 1 0 9 9 9 0 9 9 9 9 9 9 3 Sorghum 7 6 2 9 9 9 8 4 9 9 1 3 0 0 5 8 0 0 7 9 0 0 9 9 9 9 9 9 5 Soybean 9 9 3 9 9 9 9 7 7 5 8 9 9 1 8 8 6 3 8 9 1 0 8 8 9 7 8 7 0 Sugar beet 9 9 9 8 9 9 6 4 7 9 9 10 10 9 9 9 8 9 -- 9 5 2 8 9 10 9 9 9 Velvetleaf 9 9 9 9 9 9 6 4 9 9 9 9 9 5 6 8 7 6 7 9 0 0 9 10 10 8 6 8 5 Wheat 2 2 0 8 7 4 8 5 0 2 0 0 0 0 1 0 0 0 5 3 2 0 8 6 5 5 3 0 0 Wild buckwheat 9 8 0 10 7 8 8 5 7 2 7 6 2 0 0 8 2 0 4 9 0 0 7 7 7 8 -- 7 3 Wild oat 4 2 0 8 7 4 8 5 0 5 0 0 0 0 6 3 7 0 7 6 2 0 8 5 3 7 5 0 COMPOUND Rate (10 g/ha) 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 POSTEMERGENCE Barley 3 5 3 3 2 -- 4 5 4 5 5 2 0 3 8 8 6 6 2 8 6 9 9 7 4 Barnyardgrass 7 8 2 0 1 7 6 5 2 2 2 1 1 2 8 8 1 2 2 8 6 9 9 9 8 Bedstraw 7 8 5 7 7 -- 2 8 6 5 7 5 1 2 8 9 4 4 4 9 9 8 9 8 8 Blackgrass 9 -- 5 7 -- -- 7 6 5 8 8 5 6 5 9 9 6 9 -- 9 8 9 9 9 -- Cheatgrass 9 9 3 2 3 -- 5 0 0 4 5 2 0 3 9 8 5 7 3 9 8 9 9 9 8 Chickweed 4 6 7 8 2 -- 3 9 3 1 2 2 2 2 8 8 0 2 0 9 9 9 9 9 8 Cocklebur -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Corn 0 5 4 6 0 7 6 9 7 8 7 6 3 0 0 0 0 2 0 9 8 8 9 8 5 Cotton 9 9 6 7 8 9 9 9 9 9 9 9 9 0 7 9 0 0 4 10 9 9 9 10 10 Crabgrass 2 3 3 -- 0 4 1 1 0 0 0 0 0 0 0 0 3 2 0 3 6 -- 9 7 4 Giant foxtail 2 4 3 0 0 7 8 6 4 5 7 2 2 3 3 4 3 4 0 7 5 9 9 8 5 Lambsquarters 8 7 8 9 0 -- 7 4 9 9 8 5 -- 7 9 9 -- 1 6 10 -- 9 10 10 9 Morningglory 9 10 9 9 8 6 6 5 4 9 8 2 2 7 9 9 7 7 7 9 9 9 10 10 9 Nutsedge 8 9 0 0 0 -- -- -- -- -- -- -- 0 0 8 8 -- 0 -- 8 8 9 9 7 3 Rape 8 7 8 7 7 -- 3 7 8 7 6 8 8 8 9 6 6 0 2 9 9 7 10 9 7 Rice 5 9 9 9 7 8 9 9 9 8 8 8 7 7 9 9 9 9 4 9 9 9 9 9 8 Sorghum 9 9 8 6 6 8 9 9 7 8 9 9 5 2 9 9 9 8 4 9 9 9 9 9 9 Soybean 8 9 7 7 0 6 8 8 7 3 6 5 6 0 1 5 0 1 0 9 9 9 9 9 8 Sugar beet 9 8 8 9 3 -- 9 9 9 9 8 9 9 8 9 9 0 5 8 9 9 7 8 9 8 Velvetleaf 9 9 6 4 0 6 7 8 7 9 4 9 7 4 5 8 1 2 0 10 8 10 10 10 10 Wheat 2 2 2 3 0 -- 4 3 0 2 2 0 0 3 8 7 6 5 2 8 4 9 9 7 6 Wild buckwheat 7 6 9 7 3 -- 9 8 -- -- -- -- -- -- -- -- 4 1 -- -- -- 9 9 -- -- Wild oat 2 0 7 7 0 -- 2 4 3 7 6 3 2 2 7 3 9 8 0 9 9 9 9 5 4 COMPOUND Rate (10 g/ha) 113 114 115 116 117 118 119 120 121 122 123 124 125 126 127 128 129 130 131 132 133 134 POSTEMERGENCE Barley 4 7 2 2 0 2 8 5 7 7 3 2 0 2 0 0 0 0 0 0 2 0 Barnyardgrass 6 9 7 7 1 1 9 9 9 8 1 8 2 4 0 0 0 0 0 0 0 0 Bedstraw 6 7 8 9 7 7 7 7 7 7 0 0 0 2 7 0 3 3 4 7 8 -- Blackgrass 8 8 8 8 6 5 9 9 8 9 3 5 2 2 0 0 0 5 2 4 3 0 Cheatgrass 8 8 9 5 0 2 9 8 9 8 5 5 3 2 0 0 0 3 0 0 0 0 Chickweed 0 5 3 9 9 2 9 8 9 9 0 0 4 9 -- 0 0 2 4 8 0 0 Cocklebur -- -- -- -- -- -- -- -- -- -- 3 7 9 9 4 5 1 5 9 9 7 2 Corn 4 9 7 2 0 0 9 9 9 9 0 0 0 5 3 0 0 0 0 2 1 0 Cotton 9 9 9 9 9 7 9 9 9 9 9 9 9 10 8 8 6 6 6 7 4 0 Crabgrass 0 7 0 2 0 0 5 6 6 5 6 2 2 1 1 0 0 0 0 0 0 0 Giant foxtail 3 7 5 2 0 0 9 8 8 3 1 2 0 1 1 0 0 0 0 0 0 0 Lambsquarters 2 -- 5 -- -- 3 -- 10 9 9 8 9 -- -- 9 7 -- 7 -- 9 9 3 Morningglory 7 9 10 10 9 6 10 10 10 9 0 8 9 8 9 9 0 1 6 6 9 1 Nutsedge 0 7 -- -- 0 2 9 9 -- 5 -- 8 9 9 -- 3 0 7 9 -- -- -- Rape 8 9 8 9 9 8 8 9 9 9 4 8 9 9 7 7 5 8 9 8 6 5 Rice 8 9 7 8 8 3 9 9 9 9 8 7 3 9 9 2 0 2 0 0 9 0 Sorghum 7 9 9 9 7 3 9 9 9 9 0 0 0 7 8 6 0 2 0 0 2 0 Soybean 0 8 9 9 9 0 9 9 9 9 5 6 6 6 7 2 4 7 9 9 9 0 Sugar beet 2 6 5 9 9 4 9 9 9 9 5 7 9 9 9 5 5 6 6 9 8 4 Velvetleaf -- 9 9 9 9 7 10 10 10 9 9 9 9 9 0 9 8 5 9 9 0 0 Wheat 2 5 0 0 0 2 9 4 9 7 0 0 0 0 0 0 0 0 0 1 0 0 Wild buckwheat 5 3 5 9 9 6 7 8 -- 9 6 5 8 9 8 8 5 3 7 7 7 6 Wild oat 4 7 1 3 2 0 8 3 8 8 4 3 0 1 5 0 0 0 1 1 1 2 COMPOUND Rate (10 g/ha) 135 136 137 138 139 140 141 142 143 144 145 146 147 148 149 150 151 152 165 166 167 168 POSTEMERGENCE Barley 8 2 5 8 5 6 7 7 8 7 3 5 7 7 8 7 2 2 6 9 9 0 Barnyardgrass 7 4 8 7 3 7 6 9 9 2 0 6 9 9 9 3 0 4 8 9 9 9 Bedstraw 8 9 7 8 7 6 5 7 7 7 8 7 7 8 9 8 9 7 3 7 8 8 Blackgrass 7 0 7 9 3 9 8 9 9 9 8 9 9 9 9 9 9 9 8 8 9 0 Cheatgrass 7 8 8 9 8 9 7 7 9 6 3 8 9 9 9 9 7 7 8 9 10 4 Chickweed 5 0 4 7 0 5 5 6 8 6 0 3 7 9 10 9 7 3 5 8 10 3 Cocklebur 8 6 6 7 2 7 9 9 10 9 7 10 9 10 10 9 9 9 8 9 7 7 Corn 3 3 7 6 3 6 0 8 9 8 3 2 0 5 8 6 8 0 9 9 9 9 Cotton 9 6 9 9 7 9 8 9 9 8 8 9 9 9 9 9 9 9 7 9 9 9 Crabgrass 0 0 2 3 0 2 0 3 3 0 0 0 0 0 3 1 0 0 5 4 2 0 Giant foxtail 3 2 4 7 2 7 2 5 8 6 0 2 2 3 9 6 2 0 7 7 8 4 Lambsquarters 4 5 5 8 8 8 7 10 10 8 8 8 9 10 10 9 10 7 9 9 10 9 Morningglory 9 7 9 10 9 9 1 6 9 9 9 9 10 10 10 9 9 9 5 9 9 9 Nutsedge 4 -- 6 9 0 5 8 9 9 9 0 9 9 9 9 9 7 9 6 7 9 7 Rape 0 3 3 0 0 0 8 9 8 9 8 9 9 9 9 9 9 9 7 8 9 8 Rice 9 8 9 9 9 8 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 Sorghum 9 8 9 9 4 8 9 9 9 9 7 9 9 9 9 9 8 9 8 9 9 7 Soybean 8 9 6 8 9 8 9 8 9 9 8 8 9 9 9 9 9 9 9 9 9 8 Sugar beet 9 7 9 9 8 8 7 9 9 9 9 9 7 9 9 9 9 7 7 10 7 6 Velvetleaf 6 7 6 8 9 8 9 9 10 6 3 9 10 10 10 9 8 9 9 9 9 8 Wheat 8 3 7 8 6 7 6 7 8 9 4 3 7 9 9 8 3 0 8 9 8 0 Wild buckwheat -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- 7 7 10 8 Wild oat 9 3 8 9 3 7 7 6 8 9 8 5 8 5 7 9 4 2 7 9 9 1 COMPOUND Rate (10 g/ha) 169 170 171 172 173 174 175 176 177 178 179 180 181 182 183 184 185 186 187 188 189 190 POSTEMERGENCE Barley 3 4 8 9 9 6 7 7 4 6 4 4 3 8 8 9 8 9 9 8 8 8 Barnyardgrass 9 10 7 3 3 8 9 4 0 8 3 9 6 9 9 9 9 10 8 6 6 8 Bedstraw 8 8 7 5 8 7 5 2 2 0 0 3 6 8 9 9 7 8 8 7 7 7 Blackgrass 8 9 8 9 9 7 8 8 7 2 3 7 7 9 9 9 8 9 -- 7 8 9 Cheatgrass 7 8 9 9 9 5 8 7 7 0 2 6 5 9 9 9 7 9 9 7 7 7 Chickweed 10 9 2 5 7 2 7 3 3 7 2 6 7 3 5 7 5 7 7 2 3 4 Cocklebur 7 9 2 5 6 6 2 0 0 0 0 0 0 9 9 10 9 9 8 0 8 8 Corn 9 10 9 8 9 9 9 8 3 5 1 9 9 9 9 9 9 9 9 9 9 9 Cotton 9 9 6 8 9 5 6 0 0 0 0 0 7 9 9 9 9 9 9 6 7 8 Crabgrass 6 9 7 7 8 4 8 5 3 2 2 6 8 9 8 9 7 9 8 5 5 5 Giant foxtail 8 10 6 8 9 8 9 6 5 9 2 8 9 9 9 9 9 9 9 7 7 8 Lambsquarters 10 10 9 10 10 8 8 2 3 2 5 4 -- 10 10 10 10 9 7 7 8 8 Morningglory 9 10 7 8 8 7 7 0 0 0 0 8 9 9 10 10 10 9 9 7 9 9 Nutsedge 0 2 0 9 7 5 3 -- -- 6 4 0 3 8 9 8 9 3 2 2 4 5 Rape 9 9 5 4 7 7 7 0 0 0 0 0 6 8 9 9 9 9 7 0 2 0 Rice 9 9 9 8 9 9 9 5 5 0 0 9 9 9 9 10 9 10 9 9 9 9 Sorghum 9 10 9 8 9 9 9 0 3 0 0 9 9 9 9 10 9 9 9 9 9 9 Soybean 9 9 2 8 9 7 5 0 6 2 0 5 8 8 9 9 6 9 9 1 9 7 Sugar beet 9 10 6 9 9 8 8 0 2 7 5 7 8 8 7 8 7 8 7 7 7 8 Velvetleaf 9 9 4 8 7 7 8 0 0 0 0 2 8 9 9 9 9 8 8 4 3 6 Wheat 8 9 7 9 9 2 7 7 5 4 3 7 7 8 8 8 2 9 9 7 8 8 Wild buckwheat 10 9 6 9 9 9 -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Wild oat 5 8 8 9 9 0 7 7 7 2 3 6 4 9 9 9 7 9 9 8 8 8
TABLE A - TEST A COMPOUND Rate (10 g/ha) 191 192 203 204 205 206 207 208 209 210 211 212 213 214 215 216 217 218 219 220 221 222 POSTEMERGENCE Barley 8 8 9 9 9 9 9 8 8 7 9 9 7 7 2 8 9 4 3 1 0 2 Barnyardgrass 6 2 9 9 9 9 9 9 0 9 9 9 9 2 9 8 9 8 9 8 2 6 Bedstraw 7 7 8 8 9 9 9 8 3 7 9 9 9 9 8 5 5 6 6 3 3 3 Blackgrass 7 9 9 9 9 9 9 9 8 7 9 9 9 8 5 9 9 3 5 8 8 0 Cheatgrass 5 7 9 9 10 9 7 9 7 9 9 9 9 9 7 8 8 8 5 5 0 2 Chickweed 0 6 9 9 9 9 9 9 0 2 4 7 10 10 3 0 0 5 7 3 0 0 Cocklebur 7 4 8 -- 8 -- -- -- -- 0 -- 8 8 -- 0 -- -- -- -- -- 0 0 Corn 6 9 9 9 10 10 9 9 2 9 9 10 9 9 8 8 9 8 8 9 8 6 Cotton 7 8 8 8 9 9 8 9 0 7 9 10 10 10 9 6 6 9 9 2 0 4 Crabgrass 0 8 9 9 9 9 7 6 2 3 3 5 2 0 0 0 3 2 0 0 0 0 Giant foxtail 6 9 6 9 10 10 10 9 2 7 9 9 8 3 2 7 7 6 5 4 0 2 Lambsquarters 9 7 9 10 10 10 7 10 3 9 9 9 9 10 7 9 9 9 9 9 2 8 Morningglory 8 9 9 10 10 9 9 9 5 9 10 9 10 9 7 9 9 9 9 3 0 4 Nutsedge 3 3 -- 9 10 4 2 9 0 -- 2 10 9 -- -- 0 7 7 9 0 -- 0 Rape 5 5 9 10 9 9 9 9 0 5 8 9 10 10 9 0 8 7 8 9 8 8 Rice 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 8 7 Sorghum 6 9 9 9 10 10 9 9 4 9 9 10 9 9 9 9 9 6 2 8 4 0 Soybean 7 9 9 9 9 8 9 6 0 8 9 9 9 9 3 3 6 8 8 9 5 4 Sugar beet 7 8 9 10 9 10 10 10 0 4 7 8 10 9 7 8 9 9 9 8 4 8 Velvetleaf 5 2 8 9 9 9 9 9 0 9 9 9 9 6 9 3 9 9 9 2 0 5 Wheat 5 8 10 10 9 9 10 9 7 9 8 9 8 6 3 9 9 4 3 9 0 0 Wild buckwheat -- -- 9 8 9 9 9 9 0 8 6 8 9 9 8 2 9 7 9 0 3 9 Wild oat 7 9 9 9 9 10 9 9 7 9 9 10 9 9 3 9 10 9 9 2 0 0 COMPOUND Rate (10 g/ha) 223 224 225 226 227 228 229 230 231 232 233 234 235 236 237 238 239 240 241 242 243 244 POSTEMERGENCE Barley 6 7 9 5 5 5 2 7 8 8 5 0 0 8 0 0 0 9 8 9 8 8 Barnyardgrass 6 7 9 3 5 7 7 3 8 1 3 0 0 2 0 0 0 8 9 9 9 9 Bedstraw 4 7 7 3 3 5 0 9 8 9 7 0 3 7 0 0 3 9 9 9 -- 9 Blackgrass 3 3 8 6 0 9 7 9 9 9 9 0 3 8 0 0 0 9 9 9 9 10 Cheatgrass 7 5 5 2 5 5 7 8 9 9 8 0 2 8 0 0 0 9 9 9 9 9 Chickweed 2 1 8 7 0 2 2 3 3 5 0 0 2 5 0 0 0 9 9 9 10 10 Cocklebur -- 8 9 -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Corn 8 8 10 8 7 7 7 8 7 7 4 0 2 0 0 0 0 9 9 9 9 9 Cotton 9 9 8 7 8 5 7 7 9 8 7 0 0 2 0 -- 2 9 9 9 10 9 Crabgrass 0 3 2 2 0 4 0 -- -- 3 0 0 -- -- 0 0 0 8 8 9 9 8 Giant foxtail 4 5 6 4 4 6 0 8 7 5 2 0 2 7 0 0 0 9 9 10 10 9 Lambsquarters 9 8 9 9 7 8 5 8 9 7 4 0 3 7 0 0 0 9 10 10 10 10 Morningglory 9 9 9 8 8 9 9 9 9 9 7 0 1 7 0 0 0 9 9 10 10 10 Nutsedge 0 -- -- 0 -- 5 -- 0 0 0 0 0 0 0 0 0 0 9 -- 9 3 5 Rape 6 8 9 9 8 3 0 7 9 9 5 0 1 5 0 0 0 9 8 9 9 9 Rice 9 8 9 9 8 9 9 9 9 9 9 3 5 9 0 0 0 9 9 9 9 9 Sorghum 7 4 8 3 3 8 9 9 9 9 7 0 0 8 0 0 0 9 9 10 10 9 Soybean 8 9 8 9 5 7 8 7 9 9 7 0 0 0 0 0 0 8 9 9 9 9 Sugar beet 6 6 9 7 5 0 2 4 8 6 0 0 2 5 0 0 0 9 8 10 9 9 Velvetleaf 9 9 9 7 5 9 9 9 9 7 1 0 0 3 0 0 0 9 9 10 9 9 Wheat 5 5 9 2 2 4 3 6 9 9 3 0 0 5 0 0 0 8 8 9 8 8 Wild buckwheat 2 7 9 8 5 7 0 8 -- -- -- -- 3 7 -- 3 9 -- -- 10 -- -- Wild oat 8 7 9 6 0 7 5 8 9 9 7 0 1 8 0 0 0 9 9 9 9 9 COMPOUND Rate (10 g/ha) 245 246 247 248 249 250 251 252 253 254 255 256 257 258 259 260 261 262 263 264 265 266 POSTEMERGENCE Barley 9 7 9 8 6 3 5 7 5 4 2 9 8 8 8 8 8 5 5 6 7 8 Barnyardgrass 9 6 8 6 6 4 9 7 8 2 2 8 9 9 9 7 9 3 8 6 7 5 Bedstraw 9 5 7 7 7 7 7 7 7 7 7 8 9 8 7 7 7 6 5 7 7 7 Blackgrass 9 7 9 8 -- 7 9 9 7 7 7 9 9 9 9 9 9 8 2 7 8 9 Cheatgrass 9 6 8 4 3 6 8 9 7 6 5 9 9 9 9 5 9 8 4 7 8 8 Chickweed 5 -- 7 9 7 0 5 5 8 9 0 6 9 9 6 5 6 5 5 0 4 4 Cocklebur -- -- -- -- -- 0 2 8 7 7 0 1 3 2 3 1 8 0 1 4 7 7 Corn 9 9 7 9 8 8 9 9 9 5 1 0 9 9 9 9 9 7 7 8 9 9 Cotton 9 9 10 9 9 2 8 8 8 9 5 1 5 4 2 2 4 1 9 2 5 8 Crabgrass -- 5 8 -- 6 0 5 5 2 0 0 6 7 8 5 7 5 0 0 3 0 0 Giant foxtail 9 4 9 7 6 4 8 8 6 2 0 8 9 9 9 8 9 7 2 4 8 8 Lambsquarters 10 9 9 10 10 -- 7 -- -- 10 5 10 10 10 -- -- 7 7 8 7 9 -- Morningglory 10 7 9 9 9 5 9 9 9 9 7 10 10 10 7 8 10 9 9 9 9 9 Nutsedge 10 -- 9 4 -- 0 3 0 -- -- -- -- 5 9 0 0 -- -- -- 0 5 -- Rape 9 5 5 8 8 5 7 9 9 9 7 9 7 7 8 7 8 7 9 5 5 6 Rice 9 9 9 9 9 8 9 9 9 9 8 9 9 9 10 10 9 7 9 8 9 9 Sorghum 9 4 9 9 7 8 9 9 9 8 8 9 9 9 9 9 9 7 9 8 9 9 Soybean 4 1 6 7 7 6 9 9 9 9 2 8 9 9 9 9 8 8 9 5 9 9 Sugar beet 9 8 9 8 8 -- 5 3 9 8 0 4 5 7 7 5 6 5 7 0 3 5 Velvetleaf 9 2 8 9 8 5 9 8 9 2 5 9 9 9 7 7 7 3 9 8 8 8 Wheat 9 4 7 7 4 4 8 7 3 2 0 8 9 8 9 8 9 3 5 8 8 7 Wild buckwheat 9 9 -- -- -- 5 -- 9 9 9 7 9 9 8 7 8 8 9 4 8 5 8 Wild oat 9 5 8 7 6 5 5 5 7 7 2 9 9 9 9 9 9 7 6 7 7 8 COMPOUND Rate (10 g/ha) 267 268 269 270 271 272 273 274 275 276 277 278 279 280 281 282 283 284 285 286 287 288 POSTEMERGENCE Barley 9 8 4 9 9 9 3 4 9 6 4 0 0 8 0 3 9 9 9 9 9 8 Barnyardgrass 7 1 5 8 9 9 1 2 9 3 3 2 4 6 0 7 9 9 9 9 9 9 Bedstraw 9 8 7 4 9 7 1 2 8 0 0 3 4 2 3 5 8 7 6 8 7 8 Blackgrass 9 9 8 9 9 9 9 9 9 7 2 3 5 7 4 4 9 9 9 9 9 8 Cheatgrass 9 9 7 9 9 9 9 8 9 8 2 0 2 7 2 5 9 9 9 9 9 9 Chickweed 8 8 0 4 7 9 2 2 8 0 0 0 0 0 0 0 0 9 10 9 9 8 Cocklebur 8 9 0 5 1 4 0 0 7 2 2 0 2 0 0 5 -- -- -- -- -- -- Corn 8 8 7 9 10 9 7 5 9 3 0 0 0 4 0 2 9 9 9 9 7 9 Cotton 9 9 1 9 7 8 0 2 9 2 0 0 0 0 0 5 9 9 9 9 10 10 Crabgrass 2 0 0 7 8 9 2 0 8 2 2 0 0 2 0 0 6 7 6 6 6 2 Giant foxtail 5 5 0 7 9 9 2 0 9 2 3 0 0 4 0 3 10 9 9 10 10 8 Lambsquarters -- -- -- -- 9 10 2 0 10 5 5 2 6 7 3 9 10 10 10 10 10 10 Morningglory 9 9 7 9 9 9 0 1 9 6 5 2 2 1 2 6 2 9 9 9 9 9 Nutsedge 0 0 -- 8 8 -- -- -- -- 0 0 0 0 0 0 0 6 9 -- 3 -- -- Rape 9 9 7 9 9 9 0 1 9 0 0 0 0 0 0 5 9 9 9 9 10 9 Rice 9 9 5 10 9 9 9 9 9 9 9 6 5 9 8 7 9 9 9 10 10 9 Sorghum 9 9 8 9 9 9 9 9 9 9 9 0 0 7 2 8 9 9 9 10 9 9 Soybean 9 9 3 9 9 9 3 2 7 0 1 2 4 0 3 6 8 9 9 9 9 9 Sugar beet 9 9 0 9 8 9 1 1 8 2 4 5 3 3 7 7 8 8 9 9 9 9 Velvetleaf 9 7 0 7 8 9 0 0 3 0 2 0 0 0 0 4 9 9 10 9 7 9 Wheat 9 6 0 9 9 9 8 8 9 5 2 0 0 5 0 0 9 9 8 9 9 8 Wild buckwheat 9 9 9 8 8 9 2 2 9 0 0 0 0 0 0 0 9 9 9 9 9 9 Wild oat 9 9 3 9 9 9 8 8 9 8 5 0 0 7 0 4 9 9 9 9 9 9 COMPOUND Rate (10 g/ha) 289 290 291 292 293 294 295 296 297 298 299 300 301 302 303 304 305 306 307 308 309 310 POSTEMERGENCE Barley 9 7 9 4 8 2 2 6 3 2 4 9 8 9 7 5 8 6 8 7 5 7 Barnyardgrass 9 6 9 5 9 2 2 4 3 1 0 9 9 9 8 3 9 2 8 2 8 9 Bedstraw 7 3 5 3 4 3 2 3 5 0 0 7 5 7 3 5 6 6 6 6 6 6 Blackgrass 9 9 9 6 8 4 7 4 7 4 4 9 9 7 5 3 9 8 9 7 7 7 Cheatgrass 9 8 9 4 7 2 5 2 2 0 0 9 8 9 8 0 7 3 7 5 7 6 Chickweed 9 2 7 7 3 3 3 3 7 2 0 7 7 9 9 6 6 7 2 2 0 2 Cocklebur -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- 5 1 8 9 Corn 9 6 9 6 9 2 1 2 2 2 0 5 9 9 1 0 8 6 7 6 8 9 Cotton 8 7 8 6 7 1 7 3 7 4 0 9 9 9 9 6 9 8 6 9 9 9 Crabgrass 7 2 9 2 5 1 1 1 0 0 0 5 7 8 5 4 7 2 4 2 6 0 Giant foxtail 9 6 9 6 8 3 3 4 3 3 2 8 9 9 3 2 9 3 7 3 7 6 Lambsquarters 9 7 10 7 8 5 8 7 9 5 5 9 9 -- -- -- -- 4 -- 8 8 9 Morningglory 9 6 9 6 5 6 3 2 2 2 1 5 9 9 8 3 9 3 6 3 9 10 Nutsedge 4 0 -- 0 0 0 0 0 0 -- 0 -- 5 7 0 0 0 -- 4 3 3 7 Rape 0 8 9 9 7 0 3 5 5 0 0 8 9 9 9 7 7 0 7 6 7 9 Rice 9 8 9 8 7 2 8 6 7 3 0 9 9 9 3 0 9 8 9 6 9 9 Sorghum 9 7 9 8 9 2 2 3 6 3 0 9 9 9 8 3 9 8 8 4 6 8 Soybean 9 2 6 1 6 1 4 2 4 2 0 7 8 7 1 0 8 2 8 8 8 9 Sugar beet 8 7 9 9 5 3 2 7 8 2 3 8 8 9 8 5 8 2 5 6 7 8 Velvetleaf 6 6 9 7 5 3 6 1 0 0 0 7 8 8 7 1 6 3 7 5 6 9 Wheat 9 7 9 5 3 0 1 3 2 0 2 9 9 9 3 1 7 0 5 3 7 4 Wild buckwheat 8 6 9 7 8 3 0 3 6 0 2 8 7 7 8 7 7 6 7 2 5 7 Wild oat 9 8 9 5 7 2 2 5 3 3 1 8 8 8 5 2 7 5 8 2 6 9 COMPOUND Rate (10 g/ha) 311 312 313 314 315 316 317 318 319 320 321 322 323 324 325 326 327 328 329 330 331 332 POSTEMERGENCE Barley 7 6 5 0 0 0 0 0 0 0 0 9 9 9 5 3 7 2 4 0 0 0 Barnyardgrass 9 9 2 2 0 0 0 0 0 0 0 3 6 9 4 0 8 0 1 0 0 0 Bedstraw 6 7 3 5 0 0 2 0 0 0 0 6 7 9 6 6 9 5 5 0 0 0 Blackgrass 9 8 2 2 0 0 0 0 0 0 0 7 9 8 5 4 3 0 3 0 0 0 Cheatgrass 8 8 3 0 0 0 0 0 0 0 0 9 9 9 7 5 8 7 8 0 0 0 Chickweed 0 0 0 0 0 0 0 0 0 0 0 8 9 9 7 6 9 0 2 0 0 0 Cocklebur 9 7 0 0 0 0 0 7 1 2 0 9 8 9 0 0 8 0 1 0 0 0 Corn 7 7 0 0 0 0 0 0 0 0 0 9 9 9 9 1 9 4 9 0 0 0 Cotton 9 7 2 0 0 0 0 0 0 0 0 9 9 9 9 0 9 2 3 0 0 0 Crabgrass 3 0 0 0 0 0 0 0 0 0 0 7 8 5 2 0 3 0 2 0 0 0 Giant foxtail 6 5 2 0 0 0 0 0 0 0 0 8 9 9 7 0 9 5 7 0 0 0 Lambsquarters 10 -- 3 0 0 5 0 0 0 0 0 10 -- 9 5 3 9 1 3 3 0 0 Morningglory 9 9 1 7 0 0 0 4 1 2 0 5 10 10 8 1 9 1 1 0 0 0 Nutsedge 2 4 0 0 0 0 -- 0 0 -- 0 5 8 8 -- 0 7 0 0 0 0 0 Rape 7 7 3 2 0 0 2 4 2 0 0 9 9 9 9 8 9 0 0 0 0 0 Rice 9 7 7 4 0 2 2 4 0 0 0 9 9 9 9 9 9 8 9 0 0 0 Sorghum 9 8 3 3 0 0 0 0 0 0 0 9 9 9 9 1 9 1 8 0 0 0 Soybean 9 5 2 0 0 0 0 0 0 0 0 8 9 9 8 2 8 2 9 0 0 0 Sugar beet 8 -- 5 3 0 0 2 3 2 0 0 9 9 9 8 7 9 3 5 0 0 0 Velvetleaf 2 8 0 0 0 0 0 0 0 0 0 9 10 9 0 0 8 0 0 0 0 0 Wheat 4 3 3 0 0 0 0 1 0 0 0 9 9 9 9 8 1 0 7 0 0 0 Wild buckwheat 9 -- 0 2 -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Wild oat 8 5 3 0 0 0 0 1 0 0 0 9 9 9 9 4 2 7 8 0 0 0 COMPOUND Rate (10 g/ha) 333 334 335 336 337 338 339 340 341 342 POSTEMERGENCE Barley 0 0 0 0 0 9 9 9 9 8 Barnyardgrass 0 0 0 0 0 9 9 6 3 8 Bedstraw 0 0 0 0 0 7 9 2 4 8 Blackgrass 0 0 0 0 0 9 9 9 9 7 Cheatgrass 0 0 0 0 0 9 9 9 7 8 Chickweed 0 0 0 0 0 9 10 5 0 8 Cocklebur 0 0 0 0 0 10 10 1 0 9 Corn 0 0 0 0 0 9 9 9 6 9 Cotton 0 0 0 0 0 9 10 0 0 9 Crabgrass 0 0 0 0 0 7 7 1 2 7 Giant foxtail 0 0 0 0 0 9 10 7 3 8 Lambsquarters 0 0 0 0 0 10 10 2 2 10 Morningglory 0 0 0 0 0 9 9 2 3 9 Nutsedge 0 0 0 0 0 8 8 0 1 5 Rape 0 0 0 0 0 9 9 8 5 9 Rice 0 0 0 0 0 9 9 9 9 9 Sorghum 0 0 0 0 0 9 9 9 6 10 Soybean 0 0 0 0 0 9 9 2 1 6 Sugar beet 0 0 0 0 0 9 10 1 3 9 Velvetleaf 0 0 0 0 0 9 10 1 0 8 Wheat 0 0 0 0 0 9 9 9 9 9 Wild buckwheat -- -- -- -- -- -- -- -- -- -- Wild oat 0 0 0 0 0 9 9 9 9 8
TABLE A - TEST A COMPOUND Rate (10 g/ha) 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 2 3 24 25 26 27 28 29 PREEMERGENCE Barley 2 2 4 2 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 4 3 0 0 4 Barnyardgrass 0 5 3 3 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 -- 0 8 7 3 9 8 Bedstraw 4 6 0 3 7 9 0 0 0 0 0 0 0 0 0 2 0 0 2 8 -- 0 -- -- 5 9 2 0 5 Blackgrass 2 4 4 3 5 2 0 1 0 2 3 0 2 2 1 0 0 0 0 2 0 0 0 0 8 8 8 9 5 Cheatgrass 3 5 5 2 9 4 1 1 0 0 2 2 0 0 0 0 0 0 0 2 0 0 0 0 9 9 8 8 9 Chickweed 2 9 9 0 5 5 0 8 0 0 9 -- 0 5 9 -- -- 0 5 4 5 0 2 0 9 9 8 7 8 Cocklebur 0 0 0 0 2 7 -- 0 0 0 0 0 0 0 0 0 0 0 0 -- 0 0 -- 0 -- -- -- -- -- Corn 2 4 1 2 8 4 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 -- 0 8 9 7 8 9 Cotton 0 0 2 2 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 -- 0 2 7 5 0 2 Crabgrass 3 3 2 2 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 -- 0 6 7 7 7 8 Giant foxtail 2 3 1 0 0 -- 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 -- 0 7 6 5 7 7 Lambsquarters 6 8 7 0 6 0 0 0 0 0 5 5 5 0 0 0 2 0 5 0 0 0 0 0 7 6 9 9 8 Morningglory 0 2 6 4 8 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 -- 0 3 2 0 3 6 Nutsedge 3 2 0 2 0 7 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 -- -- 3 0 0 0 0 3 Rape 1 2 8 7 8 0 0 0 0 0 0 0 1 0 0 0 2 0 0 0 0 0 0 0 3 9 4 8 5 Rice 2 2 8 8 8 7 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 -- 0 9 7 3 9 9 Sorghum 2 2 0 4 3 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 -- 0 6 6 3 8 4 Soybean 0 3 4 2 4 2 0 0 2 0 3 0 0 0 0 0 0 0 0 0 0 0 -- 0 3 6 5 5 8 Sugar beet 5 7 4 6 3 1 0 0 2 2 0 0 1 3 0 0 2 0 0 0 0 0 0 0 8 8 8 6 8 Velvetleaf 3 4 3 2 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 -- 0 1 1 2 1 3 Wheat 2 7 3 2 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 2 2 0 2 Wild buckwheat 2 5 3 2 3 2 0 0 0 0 0 0 0 0 0 0 0 0 2 2 0 0 0 0 3 2 2 0 2 Wild oat 3 4 5 0 3 2 1 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 7 8 3 2 3 COMPOUND Rate (10 g/ha) 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 4 9 50 51 52 53 54 55 56 57 58 PREEMERGENCE Barley 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 2 0 3 0 0 3 0 2 Barnyardgrass 4 2 0 0 0 1 3 0 1 0 0 0 0 0 0 0 0 0 0 0 9 9 5 9 2 7 3 9 8 Bedstraw 4 0 2 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 1 8 0 5 8 2 4 7 2 Blackgrass 2 3 0 0 0 4 0 0 0 0 2 0 1 2 0 2 1 2 0 1 7 6 0 8 2 0 3 8 4 Cheatgrass 7 3 0 0 3 9 6 0 0 2 3 2 2 0 0 3 2 2 0 2 7 7 0 6 0 0 4 8 6 Chickweed 9 0 0 0 2 6 6 0 3 0 0 -- 0 0 0 5 0 0 0 -- -- 9 3 9 10 10 0 9 8 Cocklebur -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- 4 9 7 5 9 4 0 2 1 Corn 8 2 1 0 2 8 6 0 0 0 0 0 0 0 0 0 0 0 0 0 5 7 0 8 5 0 1 9 7 Cotton 3 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 6 9 0 8 3 0 0 6 2 Crabgrass 9 5 0 0 0 2 7 0 0 0 0 0 0 0 0 0 0 0 0 0 4 9 3 5 2 0 0 1 0 Giant foxtail 9 4 0 0 0 2 6 0 0 0 0 0 0 0 0 0 0 0 0 0 6 7 2 7 0 0 0 7 2 Lambsquarters 8 9 2 0 0 7 9 0 0 9 -- 3 0 0 0 0 0 0 0 0 7 9 7 9 8 -- 6 8 5 Morningglory 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 5 9 2 3 9 3 0 0 0 Nutsedge 7 0 -- 0 0 0 0 0 0 -- 0 0 0 0 0 0 0 0 0 0 9 9 -- 5 0 0 0 -- 5 Rape 0 0 0 0 2 0 2 0 2 0 0 0 0 0 0 0 0 0 0 0 7 9 2 8 8 8 5 9 8 Rice 9 4 0 0 3 8 8 2 2 0 0 2 0 0 0 0 0 0 0 0 9 10 8 9 9 7 5 8 8 Sorghum 2 2 0 0 0 5 7 0 0 0 0 0 0 0 0 0 0 0 0 0 5 5 2 2 2 1 1 6 1 Soybean 7 2 0 0 1 2 1 0 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 7 7 0 0 5 3 Sugar beet 8 2 3 2 4 8 9 0 2 2 0 0 2 0 0 0 0 0 0 0 7 9 5 8 9 7 6 7 7 Velvetleaf 2 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 2 8 2 6 0 0 0 5 1 Wheat 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 4 0 0 2 2 0 Wild buckwheat 0 0 0 3 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 7 0 3 7 0 2 4 2 Wild oat 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 5 0 5 2 0 2 3 3 COMPOUND Rate (10 g/ha) 59 60 61 62 63 64 65 66 67 68 69 70 71 72 73 74 75 76 77 7 8 79 80 81 82 83 84 85 86 87 PREEMERGENCE Barley 2 2 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 2 0 1 0 0 0 Barnyardgrass 1 2 2 0 9 9 0 0 5 2 0 0 0 0 0 0 0 0 0 2 0 0 2 6 7 2 3 3 2 Bedstraw 9 8 0 -- 0 0 0 0 0 2 0 6 2 0 0 0 0 0 0 2 0 0 0 4 7 2 0 1 0 Blackgrass 6 3 2 2 4 5 3 0 2 2 0 0 0 0 0 0 0 0 0 0 0 0 5 7 8 3 0 5 2 Cheatgrass 5 2 2 7 7 7 5 2 6 5 4 2 0 0 0 4 0 0 8 7 0 0 9 9 9 0 0 9 1 Chickweed 9 10 7 0 2 8 0 0 0 8 7 7 6 0 0 2 0 0 0 0 0 0 2 9 7 3 0 7 0 Cocklebur 8 7 0 -- 0 -- 0 0 0 0 -- 0 0 0 0 1 -- 0 -- -- 0 0 -- -- -- -- -- -- -- Corn 8 0 0 0 1 7 0 0 0 3 0 0 0 0 0 0 0 0 0 3 0 0 0 0 6 9 5 2 0 Cotton 7 7 0 0 0 4 0 0 0 6 0 1 0 0 0 0 0 0 0 0 0 0 4 2 3 2 0 3 0 Crabgrass 4 1 0 0 2 3 0 0 0 2 0 0 0 0 0 0 0 0 0 2 0 0 3 3 3 3 1 0 0 Giant foxtail 0 2 0 0 6 8 0 0 0 3 0 0 0 0 0 0 0 0 0 4 0 0 3 6 5 1 2 2 0 Lambsquarters 9 9 8 5 8 8 5 2 5 -- 3 9 -- -- 2 5 0 0 0 8 0 0 10 10 9 4 8 9 8 Morningglory 8 7 0 0 0 3 0 0 0 0 0 3 0 0 0 2 0 0 0 2 0 0 3 2 7 2 0 4 0 Nutsedge -- 10 0 0 9 9 0 -- 0 0 -- 0 0 -- 0 -- 0 -- -- 7 -- 0 0 5 10 0 0 5 0 Rape 8 8 7 0 5 8 0 0 0 6 0 1 2 0 0 0 0 0 0 1 0 0 1 8 8 1 0 5 0 Rice 8 8 7 5 7 8 8 4 8 7 5 2 0 0 0 1 0 0 2 0 0 0 5 7 7 7 5 5 0 Sorghum 2 3 1 2 6 6 0 0 3 2 0 0 0 0 0 0 0 0 1 0 0 0 7 9 9 6 2 8 0 Soybean 8 7 0 0 2 5 0 0 0 2 0 5 3 0 2 1 0 0 4 1 0 0 2 6 5 3 3 4 0 Sugar beet 9 8 5 4 6 9 1 0 5 7 7 9 7 0 2 0 0 0 3 2 0 0 7 9 9 3 6 7 3 Velvetleaf 8 3 0 0 3 4 0 0 0 2 0 0 0 0 0 1 0 0 0 0 0 0 2 2 8 2 0 2 0 Wheat 2 2 0 0 3 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 4 4 2 5 0 0 0 Wild buckwheat 8 8 3 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 9 -- 8 -- -- -- Wild oat 4 4 0 0 1 0 0 0 0 1 0 0 0 0 0 0 0 0 0 2 0 0 4 3 2 3 0 0 COMPOUND Rate (10 g/ha) 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 PREEMERGENCE Barley 0 0 0 0 0 -- 0 0 0 0 0 0 0 0 1 3 0 0 0 3 0 8 6 2 0 Barnyardgrass 7 9 0 0 2 0 1 0 0 0 1 0 0 0 1 5 1 0 0 7 6 8 8 7 4 Bedstraw 3 3 0 0 0 -- 0 0 0 0 0 0 0 0 0 0 0 0 0 7 8 4 4 0 1 Blackgrass 4 5 2 0 2 -- 2 0 0 4 3 0 0 0 1 4 0 0 0 2 3 7 8 4 2 Cheatgrass 8 7 2 0 3 -- 2 0 0 0 0 0 0 0 3 6 0 0 0 7 8 9 8 7 8 Chickweed 5 3 9 0 0 -- 8 9 5 9 7 6 7 0 2 4 0 0 0 9 9 9 7 5 9 Cocklebur -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Corn 2 3 6 6 0 0 0 0 1 0 1 0 2 0 0 0 0 0 0 5 6 5 7 3 3 Cotton 2 0 -- 0 0 0 0 2 2 0 2 0 2 0 0 1 0 0 0 8 7 7 8 5 5 Crabgrass 2 0 0 0 0 0 2 0 0 0 0 0 0 0 1 1 0 0 0 7 4 7 8 3 4 Giant foxtail 2 2 0 0 0 0 0 0 0 0 0 0 0 0 1 2 0 0 0 0 3 7 7 2 0 Lambsquarters 4 9 9 9 5 -- 1 9 0 3 7 5 5 0 7 6 0 0 0 9 10 9 9 9 8 Morningglory 1 2 1 0 0 0 0 0 0 0 0 0 0 0 0 4 0 0 0 8 8 3 6 8 5 Nutsedge 6 9 10 0 0 -- 0 0 0 0 0 0 0 0 0 0 8 0 0 5 10 9 10 -- 10 Rape 6 6 0 0 0 -- 0 1 -- 0 0 3 1 0 2 0 0 0 0 9 8 9 8 8 7 Rice 5 8 2 2 0 0 0 0 1 0 0 0 2 0 2 5 0 0 0 8 8 10 8 5 7 Sorghum 7 7 6 3 2 0 0 0 1 0 0 0 1 0 1 2 0 0 0 7 2 9 8 3 3 Soybean 1 2 1 1 0 0 0 0 2 0 1 0 0 0 0 0 0 0 0 7 6 3 7 1 1 Sugar beet 5 5 3 3 0 -- 0 7 2 2 3 7 5 0 5 7 0 0 0 9 8 8 9 7 8 Velvetleaf 2 4 0 0 0 0 0 0 0 0 0 0 0 0 0 1 1 0 0 8 5 7 8 3 6 Wheat 0 0 0 0 0 -- 2 0 0 0 0 0 0 0 0 6 0 0 0 5 2 7 7 2 0 Wild buckwheat 10 3 -- 2 -- -- 0 0 0 0 0 3 0 0 5 1 0 0 0 3 5 2 4 0 2 Wild oat 0 0 0 0 0 -- 2 0 0 0 2 0 0 0 1 2 0 0 0 6 5 6 5 2 2 COMPOUND Rate (10 g/ha) 113 114 115 116 117 118 119 120 121 122 123 124 125 126 127 128 129 130 131 132 133 134 PREEMERGENCE Barley 0 0 0 0 0 0 4 0 2 2 0 1 1 2 0 0 0 0 0 0 0 0 Barnyardgrass 2 8 1 3 2 0 9 4 5 5 0 0 0 0 0 0 0 0 0 0 0 0 Bedstraw 5 7 2 7 5 0 2 1 7 2 0 0 2 0 0 0 0 0 0 5 2 3 Blackgrass 4 6 5 3 2 0 7 5 4 2 5 6 -- 4 0 2 0 2 2 2 3 2 Cheatgrass 6 7 7 7 3 2 7 7 7 7 4 7 4 2 0 0 0 2 3 2 0 0 Chickweed 0 5 3 5 9 2 9 8 8 9 4 8 8 8 0 0 0 3 8 5 3 0 Cocklebur -- -- -- -- 9 -- -- -- -- -- 0 3 1 3 2 0 0 0 0 0 3 0 Corn 1 8 5 5 0 0 8 7 7 9 0 0 0 2 0 0 0 0 0 3 0 0 Cotton 0 3 0 8 8 0 8 3 8 6 2 3 0 1 0 0 0 0 0 0 0 0 Crabgrass 0 0 0 5 2 0 9 6 8 2 0 0 0 3 0 0 0 0 2 0 0 0 Giant foxtail 0 2 0 0 0 0 8 2 2 1 0 0 0 2 0 0 0 0 0 0 0 0 Lambsquarters -- 9 10 9 10 7 10 9 9 9 5 -- 5 2 -- 0 5 9 7 9 5 0 Morningglory 0 1 0 9 9 1 8 9 9 8 0 0 0 2 0 0 0 0 0 0 0 0 Nutsedge 0 0 3 6 8 0 2 8 8 3 0 0 0 0 0 0 0 0 2 4 0 0 Rape 3 7 0 7 6 0 9 8 8 3 1 7 3 5 0 2 0 7 4 4 2 3 Rice 1 7 3 7 5 0 9 9 8 9 2 2 0 4 0 0 0 0 0 0 0 0 Sorghum 0 4 6 4 1 0 8 5 7 9 0 0 0 2 0 0 0 0 0 0 0 0 Soybean 0 2 2 4 3 0 8 3 7 7 0 0 0 0 0 0 0 0 0 0 0 0 Sugar beet 2 5 5 8 8 2 9 8 8 8 8 5 7 8 7 4 2 5 4 8 7 2 Velvetleaf 0 3 2 7 2 0 7 6 5 2 0 0 0 0 0 0 0 0 5 0 0 0 Wheat 0 0 0 0 0 0 7 0 3 0 0 3 0 0 0 0 0 0 0 0 0 0 Wild buckwheat 0 1 0 3 3 0 3 1 5 3 0 5 2 0 2 0 3 2 4 3 5 3 Wild oat 0 2 2 0 0 0 5 2 5 3 5 4 2 2 0 0 0 0 2 2 0 2 COMPOUND Rate (10 g/ha) 135 136 137 138 139 140 141 142 143 144 145 146 147 148 149 150 151 152 165 166 167 168 PREEMERGENCE Barley 0 0 2 2 0 0 2 4 3 2 0 0 1 1 5 0 0 0 2 0 0 0 Barnyardgrass 0 0 0 2 0 0 0 4 7 1 0 4 2 4 5 0 0 0 0 0 5 0 Bedstraw 4 0 3 2 2 0 0 7 5 7 5 7 2 7 8 5 -- 7 9 0 3 0 Blackgrass 3 3 2 6 2 5 2 6 7 7 2 5 3 4 5 0 2 7 9 4 5 3 Cheatgrass 7 7 7 8 8 7 7 9 8 2 0 8 8 8 10 8 2 8 10 7 7 5 Chickweed 4 -- 6 5 0 7 0 7 7 7 -- 7 -- 8 8 7 4 7 10 9 9 10 Cocklebur 0 0 0 2 0 0 2 5 7 2 1 1 1 0 1 1 1 0 -- 0 0 8 Corn 1 0 0 0 0 0 0 6 8 6 2 1 0 4 5 2 2 1 0 4 0 0 Cotton 0 0 0 2 0 0 2 5 6 2 -- 2 0 0 7 0 0 0 0 0 0 0 Crabgrass 0 0 0 0 0 0 0 5 6 5 0 0 0 0 0 0 0 0 0 0 0 0 Giant foxtail 0 0 0 0 0 0 0 6 8 3 0 2 0 2 0 0 0 0 3 0 5 0 Lambsquarters 5 5 5 6 8 7 5 8 8 0 0 7 7 9 8 7 0 5 10 9 9 8 Morningglory 0 1 0 1 2 0 0 3 6 2 0 2 0 0 3 5 4 1 2 2 2 3 Nutsedge 0 0 0 0 0 0 4 8 9 6 0 0 4 9 7 0 0 0 0 0 0 10 Rape 0 0 0 0 0 0 2 7 9 5 0 7 1 7 8 1 0 5 9 0 0 0 Rice 3 0 2 7 0 0 7 9 9 9 8 10 9 8 9 7 5 9 6 5 8 6 Sorghum 4 0 1 0 0 0 2 6 5 5 2 4 0 2 3 0 0 2 0 0 0 0 Soybean 0 0 0 2 0 0 2 8 9 6 3 5 5 8 6 4 5 2 0 2 1 0 Sugar beet 7 7 7 7 7 7 3 9 8 3 0 8 6 8 8 7 2 5 9 2 3 0 Velvetleaf 0 2 0 0 0 2 0 3 6 2 0 2 0 0 3 0 0 0 0 3 0 1 Wheat 2 2 3 2 0 2 4 7 5 3 0 2 2 6 4 3 0 0 5 2 0 0 Wild buckwheat -- -- 0 -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- 10 2 2 0 Wild oat 3 4 2 5 0 2 6 5 2 5 0 0 5 2 2 0 0 0 9 0 0 0 COMPOUND Rate (10 g/ha) 169 170 171 172 173 174 175 176 177 178 179 180 181 182 183 184 185 186 187 188 189 190 PREEMERGENCE Barley 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 0 1 0 0 0 0 Barnyardgrass 0 0 0 1 0 3 0 0 0 0 0 0 2 9 5 2 5 4 1 0 0 0 Bedstraw 0 0 0 0 0 0 0 0 0 0 0 0 0 7 2 0 8 2 0 0 2 2 Blackgrass 0 0 3 5 5 0 2 0 1 1 0 2 0 7 8 2 7 7 3 2 3 6 Cheatgrass 2 3 2 0 2 2 3 2 0 0 0 3 0 8 7 7 8 10 7 5 5 2 Chickweed 8 7 0 2 3 0 1 2 0 0 0 4 0 5 5 5 5 -- 2 0 3 0 Cocklebur 0 2 -- 0 0 0 0 0 0 0 0 0 0 2 7 0 6 6 0 0 0 0 Corn 0 0 0 3 2 2 2 0 0 0 0 0 3 9 9 1 8 6 8 2 0 0 Cotton 0 0 0 2 2 1 0 0 0 0 0 0 0 -- 0 0 2 2 3 0 0 2 Crabgrass 0 2 0 1 6 0 2 0 0 0 0 1 1 8 6 2 6 3 7 2 3 6 Giant foxtail 0 3 0 1 3 0 4 0 0 0 0 2 1 8 6 3 9 6 7 2 2 6 Lambsquarters 7 9 2 9 8 2 0 0 0 0 0 0 0 5 5 7 5 7 0 2 0 5 Morningglory 0 0 0 3 2 2 0 0 0 0 0 0 0 5 2 2 3 4 2 0 0 0 Nutsedge 0 -- 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Rape 0 0 0 0 2 1 0 0 0 0 0 0 0 3 3 4 3 5 0 0 0 0 Rice 6 6 0 2 7 2 0 0 0 0 0 0 0 9 8 7 9 9 9 5 2 4 Sorghum 0 0 0 2 4 3 2 0 0 0 0 1 0 7 3 0 2 1 2 0 0 0 Soybean 0 0 0 3 4 2 2 0 0 0 0 0 0 6 7 3 5 8 8 0 1 0 Sugar beet 2 6 1 7 7 2 3 0 0 0 0 0 0 2 2 3 2 3 3 0 2 2 Velvetleaf 0 1 0 0 0 1 0 0 0 0 0 0 0 5 0 2 3 2 3 0 0 0 Wheat 0 0 0 0 4 0 3 0 0 0 0 0 0 7 3 0 0 2 6 0 0 0 Wild buckwheat 0 0 0 -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Wild oat 0 0 0 2 2 0 2 0 0 0 0 0 0 6 1 2 0 6 6 0 1 1 COMPOUND Rate (10 g/ha) 191 192 203 204 205 206 207 208 209 210 211 212 213 214 215 216 217 218 219 220 221 222 PREEMERGENCE Barley 0 0 2 4 9 2 1 6 0 0 0 1 1 1 0 0 1 1 0 0 0 0 Barnyardgrass 0 0 2 2 9 4 1 7 0 2 6 3 4 0 3 0 1 2 0 0 0 0 Bedstraw 0 0 0 0 7 7 7 3 0 1 2 3 5 2 2 0 2 1 2 0 0 0 Blackgrass 0 5 5 3 7 7 7 7 0 3 5 8 2 3 2 0 4 2 0 0 0 0 Cheatgrass 0 0 8 7 9 8 7 8 0 6 8 8 9 8 5 2 5 7 7 2 0 0 Chickweed 0 5 5 7 9 8 7 5 0 7 9 -- 9 9 9 4 5 9 7 0 0 0 Cocklebur 0 0 -- -- 10 10 8 2 0 0 -- 0 0 -- -- -- -- -- 0 0 -- -- Corn 0 6 5 9 7 8 3 8 0 0 8 6 9 2 0 0 0 0 0 0 0 0 Cotton 0 0 0 1 5 3 2 4 0 0 3 2 0 7 0 0 0 0 0 0 0 0 Crabgrass 0 4 5 9 9 8 4 6 0 2 6 2 6 1 0 0 2 2 0 0 0 0 Giant foxtail 0 6 0 8 9 7 2 8 0 2 8 4 2 1 0 0 2 2 0 0 0 0 Lambsquarters 0 2 5 9 -- 9 5 5 0 3 9 8 9 9 9 6 3 9 2 0 -- 0 Morningglory 0 0 2 4 7 7 2 6 0 0 0 2 3 2 0 0 0 0 0 0 0 0 Nutsedge 0 0 5 7 10 -- 0 8 0 0 0 0 0 3 0 0 2 0 0 0 0 0 Rape 0 0 0 3 8 1 1 9 0 0 7 5 3 6 1 0 2 1 0 0 0 0 Rice 0 4 8 9 8 9 8 9 0 0 6 5 9 3 2 0 0 0 0 0 0 0 Sorghum 0 0 2 2 8 6 3 9 0 2 2 8 2 0 0 0 0 0 0 0 0 0 Soybean 0 3 4 4 5 7 5 4 0 2 6 2 7 7 0 0 0 0 0 0 0 0 Sugar beet 0 0 2 5 8 6 1 7 0 2 3 2 9 8 5 2 2 2 0 0 0 0 Velvetleaf 0 0 0 4 6 5 2 2 0 0 5 1 7 0 3 0 1 0 0 0 0 0 Wheat 0 0 4 8 8 7 6 6 0 2 8 6 1 1 0 0 0 1 0 0 0 0 Wild buckwheat -- -- 3 0 5 0 3 2 0 2 1 3 2 4 2 0 7 1 1 0 0 0 Wild oat 0 3 5 5 8 7 7 5 0 2 6 3 2 2 2 2 3 2 2 0 0 0
TABLE A - TEST A COMPOUND Rate (10 g/ha) 223 224 225 226 227 228 229 230 231 232 233 234 235 236 237 238 239 240 241 242 243 244 PREEMERGENCE Barley 0 0 0 0 0 0 -- 0 0 0 0 0 0 0 0 0 0 5 5 6 2 2 Barnyardgrass 0 0 0 0 0 0 1 0 1 0 0 0 0 0 0 0 0 7 8 6 6 5 Bedstraw 0 1 0 0 0 0 -- 0 0 0 2 2 0 0 0 2 0 2 3 4 7 5 Blackgrass 0 0 0 0 0 3 -- 2 0 0 2 0 0 0 0 2 3 7 7 5 9 5 Cheatgrass 0 0 0 0 0 7 -- 7 7 7 4 0 0 0 0 0 0 8 8 7 7 6 Chickweed 7 5 0 4 0 0 -- 2 3 0 0 0 0 0 0 0 0 5 9 9 9 9 Cocklebur -- 0 0 -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Corn 0 0 0 0 0 0 2 1 6 2 0 0 0 0 0 0 0 9 9 6 9 8 Cotton 0 0 0 0 0 0 0 -- 2 0 -- 0 0 0 0 0 0 4 2 5 2 6 Crabgrass 0 2 0 0 0 2 0 0 4 0 0 0 0 0 0 0 0 9 9 9 9 9 Giant foxtail 0 2 0 0 0 1 1 0 2 0 0 0 0 0 0 0 0 7 9 8 6 6 Lambsquarters 7 3 -- -- -- 4 -- 3 3 2 0 0 0 0 0 0 0 5 9 9 9 9 Morningglory 0 0 0 0 0 0 2 1 0 1 1 0 0 1 0 0 0 6 4 5 5 3 Nutsedge 0 0 0 0 0 -- 0 0 5 0 -- 0 0 -- 0 -- 0 5 9 7 8 2 Rape 2 1 0 0 0 0 -- 0 0 0 0 0 0 0 0 0 0 4 5 6 7 6 Rice 0 0 3 0 0 0 1 3 4 3 0 0 0 0 0 0 0 9 9 8 9 7 Sorghum 0 0 0 0 0 2 2 1 4 2 0 0 0 0 0 0 0 9 8 3 8 7 Soybean 0 2 2 0 0 0 3 2 6 2 0 0 0 0 0 0 0 7 5 4 5 3 Sugar beet 0 3 0 0 0 0 -- 0 0 0 0 1 0 0 0 0 0 4 5 8 7 8 Velvetleaf 0 2 0 0 0 0 1 1 1 0 0 0 0 0 0 0 0 4 2 6 7 6 Wheat 0 0 0 0 0 0 -- 0 4 2 3 0 0 0 0 0 0 8 6 5 4 6 Wild buckwheat 3 0 0 0 0 0 -- 0 2 0 0 2 0 0 0 0 0 3 2 7 3 3 Wild oat 0 0 0 0 0 2 -- 2 2 4 2 0 0 0 0 0 0 6 6 6 3 6 COMPOUND Rate (10 g/ha) 245 246 247 248 249 250 251 252 253 254 255 256 257 258 259 260 261 262 263 264 265 266 PREEMERGENCE Barley 7 0 0 0 0 0 0 0 1 0 0 4 5 0 0 0 7 0 0 0 0 0 Barnyardgrass 9 2 2 0 0 0 3 0 2 1 0 2 2 4 4 1 5 0 0 2 0 1 Bedstraw 8 5 0 2 0 0 7 4 2 0 3 7 6 5 2 0 3 0 0 2 0 0 Blackgrass 7 0 0 2 0 1 7 5 5 5 2 5 3 7 5 1 7 0 0 0 0 6 Cheatgrass 8 0 2 0 0 2 5 6 6 6 0 8 8 8 7 7 8 0 0 5 6 7 Chickweed 8 2 5 8 3 3 9 4 9 7 0 2 8 5 7 2 7 0 0 0 0 2 Cocklebur -- -- -- -- -- 0 2 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 Corn 9 0 0 2 0 0 3 5 7 2 0 7 5 8 7 2 8 2 0 2 2 0 Cotton 8 0 0 2 0 0 3 4 0 1 0 0 2 5 0 -- 2 0 0 0 0 0 Crabgrass 9 6 7 2 2 0 5 0 0 0 0 7 6 5 6 0 5 0 0 0 0 0 Giant foxtail 9 2 6 2 2 0 5 2 0 0 0 5 6 9 5 1 8 0 0 0 0 0 Lambsquarters 9 0 5 7 0 -- 9 5 9 -- 2 4 7 9 9 2 3 2 0 0 7 2 Morningglory 6 0 0 2 0 0 0 0 2 2 0 3 3 3 1 0 0 0 0 1 0 1 Nutsedge 9 6 -- 0 -- 0 0 0 0 0 0 9 0 3 0 0 8 0 0 0 0 0 Rape 7 0 0 2 0 0 7 4 5 3 2 5 5 7 3 0 3 0 0 0 0 0 Rice 9 2 2 2 0 0 3 2 5 7 0 8 5 7 8 5 9 0 0 0 0 3 Sorghum 9 0 0 0 0 0 4 0 4 2 0 8 5 7 8 3 9 0 0 2 2 2 Soybean 3 0 2 2 0 0 2 2 3 4 0 4 2 3 2 0 2 0 0 2 2 0 Sugar beet 7 0 5 8 7 0 7 3 5 -- 0 2 5 3 2 0 3 0 0 0 0 0 Velvetleaf 5 2 2 0 0 0 3 0 4 0 0 4 0 4 0 0 1 0 0 0 0 2 Wheat 4 0 0 0 0 0 0 3 0 0 0 6 7 6 4 2 5 0 0 0 0 0 Wild buckwheat 7 3 -- 5 -- 0 -- 0 3 2 2 2 0 0 2 0 3 0 0 0 0 0 Wild oat 6 0 0 0 0 0 2 2 1 2 0 7 4 6 4 3 5 0 0 3 0 0 COMPOUND Rate (10 g/ha) 267 268 269 270 271 272 273 274 275 276 277 278 279 280 281 282 283 284 285 286 287 288 PREEMERGENCE Barley 0 0 0 0 0 1 0 0 7 0 0 0 0 0 0 0 3 1 0 1 1 2 Barnyardgrass 2 0 0 0 1 2 0 0 8 0 0 0 0 0 0 0 0 2 0 3 2 0 Bedstraw 0 0 0 0 1 2 0 0 2 0 0 0 0 0 0 0 0 2 1 4 0 4 Blackgrass 3 3 0 7 5 5 2 2 8 0 0 0 0 0 1 0 6 5 1 4 0 2 Cheatgrass 8 9 5 9 8 8 7 5 8 0 0 0 0 0 0 0 8 8 5 7 2 8 Chickweed 0 2 0 0 6 8 0 0 8 0 0 0 -- 0 0 0 8 9 8 8 9 8 Cocklebur 0 0 0 0 0 0 0 0 0 0 0 0 0 -- 0 0 4 5 4 6 6 5 Corn 5 1 0 1 0 2 1 2 8 0 0 0 0 0 0 0 5 3 0 3 2 2 Cotton 2 3 0 2 2 3 0 2 6 0 0 0 0 0 0 0 2 1 0 2 2 6 Crabgrass 0 0 0 5 4 8 2 0 9 0 0 0 0 0 0 0 5 4 5 8 8 5 Giant foxtail 0 0 0 0 0 9 1 0 9 0 0 0 0 0 0 0 2 3 3 3 3 5 Lambsquarters -- 5 3 -- 5 9 0 0 4 -- 0 -- 0 0 0 -- -- 9 9 3 9 8 Morningglory 0 3 0 0 3 2 0 0 3 0 0 0 0 0 0 0 3 3 1 5 3 5 Nutsedge 0 0 0 8 0 0 0 0 10 0 0 0 0 0 0 0 0 2 0 -- 0 8 Rape 1 1 0 0 0 0 0 0 2 0 0 0 0 0 0 0 8 8 6 8 9 6 Rice 5 3 0 5 5 9 5 3 9 0 0 0 0 0 0 0 5 3 0 2 2 3 Sorghum 5 3 0 2 2 1 1 2 9 0 0 0 0 0 0 0 3 3 0 5 0 7 Soybean 5 2 0 2 0 1 1 0 5 0 0 0 0 0 0 0 4 1 0 0 3 2 Sugar beet 3 1 0 0 -- 3 0 0 2 0 0 0 1 0 0 3 7 8 4 5 8 7 Velvetleaf 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 4 4 3 3 2 6 Wheat 3 0 0 4 3 0 2 0 7 0 0 0 0 0 0 0 3 2 0 0 0 0 Wild buckwheat 0 0 0 5 6 0 0 0 0 -- -- -- -- -- -- -- 4 5 1 0 0 2 Wild oat 3 5 0 5 3 3 2 2 6 0 0 0 0 0 0 0 2 2 0 2 2 2 COMPOUND Rate (10 g/ha) 289 290 291 292 293 294 295 296 297 298 299 300 301 302 303 304 305 306 307 308 309 310 PREEMERGENCE Barley 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Barnyardgrass 0 0 0 0 0 0 0 0 0 0 0 1 3 3 0 0 3 2 0 0 0 0 Bedstraw 1 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 2 0 Blackgrass 3 0 4 0 0 0 3 3 2 2 2 2 0 4 0 0 0 0 3 3 0 0 Cheatgrass 6 2 6 0 0 0 0 1 0 0 0 4 6 6 0 0 7 3 2 0 0 0 Chickweed 7 0 4 0 0 2 2 2 2 -- 0 0 2 9 0 0 3 2 0 0 0 0 Cocklebur 0 0 0 0 0 0 0 0 0 0 0 -- -- -- -- -- -- -- 0 0 0 -- Corn 2 0 2 0 0 0 0 0 0 0 0 2 1 5 0 0 4 1 4 2 0 0 Cotton 0 0 0 0 0 0 0 0 0 0 0 2 2 2 0 0 2 0 -- 0 0 2 Crabgrass 3 0 4 0 0 0 2 0 0 0 0 5 2 5 0 0 7 3 0 0 0 0 Giant foxtail 3 0 5 0 0 0 0 0 0 0 0 6 2 8 1 0 8 2 0 0 0 0 Lambsquarters 7 5 6 0 0 0 2 4 10 4 3 3 9 9 0 0 5 5 2 3 3 5 Morningglory -- 0 0 0 0 0 0 0 0 0 0 0 1 0 0 0 2 0 0 0 0 3 Nutsedge 0 0 8 0 0 0 0 0 0 0 0 0 0 8 0 0 0 0 0 0 0 0 Rape 0 1 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 2 0 0 Rice 0 0 0 0 0 0 0 0 0 0 0 0 3 7 0 0 8 2 0 0 0 0 Sorghum 2 0 2 0 0 0 0 0 0 0 0 3 1 3 0 0 5 1 0 0 0 0 Soybean 0 0 -- 0 0 0 0 0 0 0 0 1 3 2 0 0 2 0 0 1 0 2 Sugar beet 6 0 5 0 0 0 0 0 0 0 0 0 0 2 0 0 6 0 0 2 0 2 Velvetleaf 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 0 0 4 0 3 3 Wheat 0 0 4 0 0 0 0 0 0 0 0 0 2 5 0 0 0 0 0 0 0 0 Wild buckwheat 2 2 2 0 0 0 2 0 0 2 0 0 0 0 0 0 0 2 -- 2 -- -- Wild oat 2 2 3 0 0 0 2 0 0 0 0 2 6 2 0 0 0 0 0 0 0 0 COMPOUND Rate (10 g/ha) 311 312 313 314 315 316 317 318 319 320 321 322 323 324 325 326 327 328 329 330 331 332 PREEMERGENCE Barley 0 0 0 0 0 0 0 0 0 0 0 2 8 3 0 0 2 0 0 0 0 0 Barnyardgrass 0 0 0 0 0 0 0 0 0 0 0 1 1 3 0 0 3 1 1 0 0 0 Bedstraw 0 0 0 0 0 0 2 0 0 0 0 1 8 5 0 0 5 0 0 0 0 0 Blackgrass 0 1 1 1 0 0 0 0 0 0 0 7 8 7 5 0 5 0 0 0 0 0 Cheatgrass 0 3 0 0 0 0 0 0 0 0 0 9 9 9 7 0 7 0 3 0 0 0 Chickweed 0 0 0 0 0 0 0 0 0 0 0 9 9 9 8 2 9 0 2 0 -- -- Cocklebur 3 2 -- 0 0 0 0 0 0 0 0 0 0 1 0 0 1 0 0 0 0 0 Corn 0 0 0 0 0 0 0 0 0 0 0 9 8 9 7 0 9 2 2 0 0 0 Cotton 2 -- 0 0 0 0 0 0 0 0 0 2 5 8 1 0 5 2 2 0 0 0 Crabgrass 0 0 0 0 0 0 0 0 0 0 0 5 7 6 0 0 5 2 0 0 0 0 Giant foxtail 2 2 0 0 0 0 0 0 0 0 0 3 8 8 0 0 6 0 0 0 0 0 Lambsquarters 0 5 -- 10 0 0 0 0 0 0 0 9 9 9 3 2 9 0 3 0 0 0 Morningglory 5 3 0 0 0 0 0 0 0 0 0 2 5 3 1 1 2 0 0 0 0 0 Nutsedge 0 0 0 0 0 0 0 0 0 0 0 5 3 9 -- 0 7 0 0 0 0 0 Rape 0 0 0 0 0 0 0 0 0 0 0 7 9 9 0 0 9 0 0 0 0 0 Rice 0 0 0 0 0 0 0 0 0 0 0 9 9 9 8 3 9 0 3 0 0 0 Sorghum 0 0 0 0 0 0 0 0 0 0 0 8 8 8 3 0 8 0 2 0 0 0 Soybean 3 2 0 0 0 0 0 0 0 0 0 7 9 9 2 0 4 0 2 0 0 0 Sugar beet 0 3 0 0 0 0 0 0 0 0 0 9 8 8 5 3 9 0 0 0 0 0 Velvetleaf 2 3 0 0 0 0 0 0 0 0 0 5 3 8 0 0 1 0 0 0 0 0 Wheat 0 0 0 0 0 0 0 0 0 0 0 5 8 6 2 0 0 0 0 0 0 0 Wild buckwheat -- -- -- -- -- 0 -- -- -- -- 0 -- -- -- -- -- -- -- -- -- -- -- Wild oat 0 0 0 0 0 0 0 0 0 0 0 7 8 6 5 2 2 0 2 0 0 0 COMPOUND Rate (10 g/ha) 333 334 335 336 337 338 339 340 341 342 Barley 0 0 0 0 0 5 3 0 0 2 Barnyardgrass 0 0 0 0 0 2 4 0 0 0 Bedstraw 0 0 0 0 0 2 0 0 0 0 Blackgrass 0 0 0 0 0 0 5 5 2 0 Cheatgrass 0 0 0 0 0 9 9 7 3 8 Chickweed -- -- 0 0 0 9 9 -- 0 7 Cocklebur 0 0 0 0 0 2 6 0 0 2 Corn 0 0 0 0 0 8 7 0 0 4 Cotton 0 0 0 0 0 4 6 0 -- 2 Crabgrass 0 0 0 0 0 2 9 0 0 3 Giant foxtail 0 0 0 0 0 5 9 0 0 3 Lambsquarters 0 0 0 0 0 8 9 0 0 9 Morningglory 0 0 0 0 0 5 2 0 0 4 Nutsedge 0 0 0 0 0 6 4 0 0 0 Rape 0 0 0 0 0 5 9 0 0 5 Rice 0 0 0 0 0 7 9 3 0 8 Sorghum 0 0 0 0 0 1 9 0 0 9 Soybean 0 0 0 0 0 6 5 0 0 3 Sugar beet 0 0 0 0 0 2 9 0 0 7 Velvetleaf 0 0 0 0 0 2 5 0 0 2 Wheat 0 0 0 0 0 8 8 2 0 5 Wild buckwheat -- -- -- -- -- -- -- -- -- -- Wild oat 0 0 0 0 0 2 2 2 0 4
TEST B
The compounds evaluated in this test were formulated in a non-phytoxic solvent and applied to the soil surface before plant seedlings emerged (preemergence application), to water that covered the soil surface (paddy application), and to plants that were in the one-to-four leaf stage (postemergence application). A sandy loam soil was used for the preemergence and postemergence tests, while a silt loam soil was used in the paddy test. Water depth was approximately 2.5 cm for the paddy test and was maintained at this level for the duration of the test.
Plant species in the preemergence and postemergence tests consisted of barley (Hordeum vulgare), bedstraw (Galium aparine), blackgrass (Alopecurus myosuroides), chickweed (Stellaria media), corn (Zea mays), cotton (Gossypium hirsutum), crabgrass (Digitaria sanguinalis), downy brome (Bromus tectorum), duck salad (Heteranthera limosa), giant foxtail (Setaria faberii), lambsquarters (Chenopodium album), morningglory (Ipomoea hederacea), pigweed (Amaranthus retroflexus), rape (Brassica napus), ryegrass (Lolium multiflorum), sorghum (Sorghum bicolor), soybean (Glycine max), speedwell (Veronica persica), sugar beet (Beta vulgaris), velvetleaf (Abutilon theophrasti), wheat (Triticum aestivum), wild buckwheat (Polygonum convolvulus), and wild oat (Arena fatua). All plant species were planted one day before application of the compound for the preemergence portion of this test. Plantings of these species were adjusted to produce plants of appropriate size for the postemergence portion of the test. Plant species in the paddy test consisted of barnyardgrass (Echinochloa crus-galli), rice (Oryza sativa), and umbrella sedge (Cyperus difformis).
All plant species were grown using normal greenhouse practices. Visual evaluations of injury expressed on treated plants, when compared to untreated controls, were recorded approximately fourteen to twenty-one days after application of test compounds. Plant response ratings, summarized in Table B, are recorded on a 0 to 10 scale where 0 is no injury and 10 is complete control. A dash (-) response means no test result.
TABLE B - COMPOUND Rate (125 g/ha) 2 7 125 209 254 269 292 POSTEMERGENCE Barley Igri 10 8 0 0 8 9 8 Bedstraw 10 5 8 0 10 10 10 Blackgrass 10 9 8 6 9 10 10 Chickweed 10 3 10 0 10 6 9 Corn 10 7 8 7 10 9 10 Cotton 7 6 10 0 9 7 9 Crabgrass 8 6 0 0 0 0 10 Downy brome 10 9 0 2 9 9 6 Duck salad -- -- 4 0 3 7 8 Giant foxtail 10 8 3 5 7 5 10 Lambsquarters 10 10 10 0 8 2 9 Morningglory 10 7 10 5 10 8 10 Pigweed 8 6 9 0 9 7 7 Rape 10 0 10 0 10 10 10 Ryegrass 10 5 0 2 9 9 7 Sorghum 10 7 5 7 9 8 10 Soybean 10 6 9 0 10 8 3 Speedwell 8 0 6 0 4 5 9 Sugar beet 10 7 10 0 9 4 9 Velvetleaf 10 6 10 0 7 4 8 Wheat 9 6 0 0 5 6 8 Wild buckwheat 10 4 9 0 10 10 -- Wild oat 10 8 0 0 9 8 9 Barnyardgrass 9 2 7 0 8 9 7 Rice Japonica 9 8 7 6 8 9 6 Umbrella sedge 9 5 9 0 8 8 4 COMPOUND Rate (125 g/ha) 2 7 125 209 254 269 292 PREEMERGENCE Barley Igri 10 4 0 0 9 0 2 Bedstraw 10 5 8 5 10 8 3 Blackgrass 10 7 9 0 10 10 0 Chickweed 10 4 9 5 10 3 9 Corn 9 0 2 0 10 0 0 Cotton 5 0 3 0 9 2 0 Crabgrass 9 4 3 3 7 6 3 Downy brome 10 7 0 7 9 9 2 Duck salad -- -- -- -- -- -- -- Giant foxtail 10 5 0 0 8 6 0 Lambsquarters 10 8 10 0 9 10 0 Morningglory 6 3 7 0 9 0 0 Pigweed 10 7 9 0 9 8 7 Rape 10 3 10 0 10 3 3 Ryegrass 10 5 4 4 9 0 3 Sorghum 9 7 4 3 9 3 4 Soybean 8 0 3 0 10 3 0 Speedwell 10 9 10 0 9 10 4 Sugar beet 10 7 10 4 10 -- 6 Velvetleaf 9 4 7 0 8 4 3 Wheat 10 7 0 0 3 0 0 Wild buckwheat 10 2 9 5 9 9 7 Wild oat 9 3 2 0 9 2 0 Barnyardgrass -- -- -- -- -- -- -- Rice Japonica -- -- -- -- -- -- -- Umbrella sedge -- -- -- -- -- -- -- COMPOUND Rate (62 g/ha) 1 2 3 5 7 11 13 14 35 50 51 53 58 59 60 63 64 71 77 78 81 82 83 84 86 88 89 102 103 POSTEMERGENCE Barley Igri 10 10 9 10 8 9 9 9 5 9 9 9 6 8 7 9 9 3 5 4 8 8 9 9 8 8 8 9 9 Bedstraw 10 10 10 10 5 9 10 8 10 10 10 10 10 10 10 9 9 9 7 9 8 9 10 10 10 10 10 10 10 Blackgrass 9 10 10 10 8 9 9 7 10 10 9 9 9 9 9 10 10 7 7 8 10 10 10 9 9 9 10 9 9 Chickweed 9 10 10 10 0 10 9 9 10 9 10 9 9 10 10 10 10 9 7 9 9 10 10 10 9 9 10 9 9 Corn 7 10 10 10 7 10 10 10 10 8 10 7 10 10 9 10 10 7 7 8 4 9 9 10 4 8 9 6 0 Cotton 6 7 9 7 5 9 8 9 8 10 10 10 9 10 10 9 10 10 7 8 8 9 10 9 9 9 9 7 8 Crabgrass 8 7 8 10 5 7 10 7 4 5 8 8 4 0 3 7 10 6 7 5 7 4 5 6 3 3 4 1 2 Downy brome 9 10 10 10 8 9 9 7 10 8 8 9 6 8 7 9 8 4 6 3 7 7 6 9 6 8 5 9 9 Duck salad -- -- -- -- -- -- -- -- -- 10 10 10 8 10 10 9 10 10 7 9 4 9 9 3 9 9 9 6 9 Giant foxtail 8 10 10 10 7 10 10 10 9 10 10 10 7 6 4 10 10 5 7 8 9 9 10 9 6 6 7 7 7 Lambsquarters 10 10 10 10 9 10 10 8 10 10 10 10 9 10 10 10 10 10 10 10 9 9 10 10 10 9 10 10 10 Morningglory 7 10 10 10 6 9 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 9 9 10 10 10 9 Pigweed 8 7 7 10 4 9 10 6 10 10 10 10 10 10 10 10 10 10 10 10 9 10 10 9 9 8 10 9 10 Rape 7 10 10 10 0 10 10 10 4 10 10 10 10 10 10 10 10 8 10 10 9 10 10 10 10 10 10 9 10 Ryegrass 10 10 5 10 4 9 10 9 9 9 10 10 6 9 9 10 10 6 8 6 6 6 6 10 5 6 5 6 4 Sorghum 7 10 10 10 7 10 10 10 10 8 10 7 7 8 7 10 10 7 10 10 10 10 10 10 9 8 9 10 10 Soybean 8 10 10 10 4 10 10 10 10 10 10 10 10 10 10 10 10 9 9 9 9 10 10 9 9 9 9 8 9 Speedwell 7 6 4 10 0 0 8 0 5 6 10 9 9 10 8 8 8 4 6 6 3 9 0 10 9 9 10 -- -- Sugar beet 10 10 10 10 7 10 10 9 10 10 10 10 10 10 10 10 10 9 10 10 9 9 10 10 10 9 10 10 10 Velvetleaf 8 10 10 10 4 8 10 7 10 10 10 10 10 10 8 10 10 10 8 10 9 9 10 7 9 9 9 7 9 Wheat 9 9 9 10 6 9 9 9 7 9 9 9 5 6 4 9 9 2 3 2 8 8 5 9 6 6 7 9 9 Wild buckwheat -- 10 10 10 2 9 10 9 0 8 10 9 8 10 10 9 9 3 6 9 9 9 9 10 8 9 9 9 9 Wild oat 10 10 10 10 8 9 10 8 9 7 9 8 5 8 7 8 8 2 2 4 9 4 3 9 5 5 4 8 8 Barnyardgrass 8 8 7 9 0 8 8 8 9 9 9 9 8 8 7 9 10 8 9 9 9 9 9 8 9 9 9 4 7 Rice Japonica 8 8 8 9 2 8 8 7 8 9 9 9 8 9 9 8 9 9 9 9 9 9 9 9 9 8 8 6 6 Umbrella sedge 9 9 9 9 4 9 6 3 5 9 10 9 8 9 9 9 9 3 9 9 9 9 9 6 9 8 8 6 9 COMPOUND Rate (62 g/ha) 108 109 110 111 112 114 115 116 117 118 119 120 121 122 125 166 167 170 172 173 203 208 POSTEMERGENCE Barley Igri 8 10 10 9 8 9 4 6 4 5 10 9 10 10 0 9 9 9 9 9 9 9 Bedstraw 10 10 10 10 10 10 10 10 10 -- 10 10 10 10 6 10 10 -- 9 10 10 10 Blackgrass 10 10 10 10 10 9 9 9 9 9 10 10 10 10 8 9 9 9 10 10 9 10 Chickweed 10 10 10 10 9 9 9 10 10 3 10 10 10 10 9 10 10 10 9 9 10 9 Corn 10 9 10 10 8 9 9 8 5 5 10 10 10 10 5 10 10 10 9 9 10 10 Cotton 10 9 10 10 9 9 9 9 10 3 10 10 10 10 9 8 10 10 6 9 9 10 Crabgrass 7 9 9 6 6 2 2 2 0 0 8 7 9 7 0 8 8 10 8 9 10 10 Downy brome 9 9 10 9 7 6 0 8 0 0 10 9 9 9 0 9 9 9 9 9 10 9 Duck salad 10 9 10 8 10 4 4 7 6 5 9 9 9 9 4 9 9 9 7 5 9 10 Giant foxtail 6 9 10 9 6 8 7 9 3 0 10 10 10 7 2 9 9 10 9 9 7 10 Lambsquarters 10 10 10 10 10 9 10 9 5 3 10 10 10 10 10 10 10 10 9 9 10 10 Morningglory 10 8 10 10 10 8 10 10 10 9 10 10 10 10 10 10 10 10 9 10 10 10 Pigweed 10 10 10 10 10 7 6 9 8 7 10 10 10 10 8 10 10 10 9 9 10 10 Rape 10 10 10 10 10 9 9 10 10 10 10 10 10 10 9 10 10 10 6 9 10 10 Ryegrass 10 10 10 9 7 9 5 9 6 6 10 6 10 10 0 9 9 10 9 9 10 10 Sorghum 10 9 10 10 10 8 9 9 9 0 10 10 10 10 5 10 10 10 6 9 10 10 Soybean 10 9 10 10 9 8 9 10 9 1 10 10 10 10 9 9 10 10 9 9 10 9 Speedwell -- 10 10 9 10 9 8 10 10 9 10 8 10 0 -- 9 5 9 10 8 7 8 Sugar beet 10 9 10 10 10 9 9 9 9 5 10 10 10 10 10 10 10 10 9 9 10 10 Velvetleaf 10 10 10 10 10 8 9 9 9 4 10 10 10 9 9 9 10 10 9 8 10 10 Wheat 5 9 9 8 5 6 4 4 0 0 9 9 9 9 0 9 9 9 9 9 9 9 Wild buckwheat 10 9 9 10 9 9 9 10 9 9 10 10 8 10 9 9 9 9 9 10 9 10 Wild oat 9 9 10 7 6 9 4 8 5 3 9 6 9 9 0 9 9 9 9 9 9 9 Barnyardgrass 9 9 9 8 8 8 9 8 6 8 9 9 9 9 4 9 0 10 7 6 9 10 Rice Japonica 9 9 9 9 8 8 7 7 8 7 8 8 9 9 6 9 8 9 7 9 9 9 Umbrella sedge 9 8 9 8 8 9 9 9 9 8 9 9 9 9 9 10 9 9 8 8 9 9 COMPOUND Rate (62 g/ha) 209 211 212 213 214 217 218 219 225 229 230 231 232 252 254 256 258 259 261 266 267 268 POSTEMERGENCE Barley Igri 0 10 9 7 8 9 8 7 9 9 9 9 9 9 8 9 10 9 10 9 9 9 Bedstraw 0 10 10 10 10 8 8 10 9 10 10 10 10 10 10 10 9 9 10 10 10 10 Blackgrass 5 10 9 8 9 9 8 8 8 10 9 9 10 10 9 9 9 9 10 10 10 10 Chickweed 0 10 8 10 10 9 10 10 10 10 10 10 10 7 10 10 10 9 9 6 10 10 Corn 4 10 10 10 10 10 10 10 10 9 9 10 10 10 9 10 10 10 10 10 10 10 Cotton 0 10 10 10 10 10 9 7 10 2 -- 8 7 8 9 0 5 8 4 5 9 9 Crabgrass 0 7 7 8 5 8 6 4 9 6 4 9 9 7 0 9 10 7 10 0 4 3 Downy brome 0 10 9 8 8 9 8 7 10 9 9 9 10 10 8 9 9 10 9 9 10 10 Duck salad 0 10 9 9 10 9 8 6 8 8 8 0 0 6 3 6 9 5 7 9 3 4 Giant foxtail 5 10 10 10 7 9 8 6 10 8 7 9 9 9 6 10 10 10 10 10 6 7 Lambsquarters 0 10 10 10 10 10 10 10 10 10 10 10 10 9 8 10 10 10 10 8 10 10 Morningglory 4 10 10 10 10 10 10 10 9 9 10 9 10 10 10 10 10 9 10 10 10 10 Pigweed 0 10 7 10 10 10 10 10 10 10 9 10 10 8 9 10 10 10 10 5 10 10 Rape 0 9 10 10 10 10 9 9 10 8 9 10 9 10 10 10 10 9 10 9 10 10 Ryegrass 0 -- 8 10 8 9 9 8 10 5 2 9 9 5 9 10 9 10 10 2 10 10 Sorghum 7 10 10 10 10 10 9 8 10 8 9 10 10 10 9 10 10 10 10 10 10 10 Soybean 0 10 10 10 10 9 10 10 10 9 9 10 9 8 10 10 10 9 9 10 10 10 Speedwell 0 9 3 10 9 7 3 5 7 9 0 -- 10 8 4 3 0 3 3 3 10 0 Sugar beet 0 10 8 10 10 9 10 10 10 8 8 10 10 8 9 9 9 10 10 6 10 10 Velvetleaf 0 10 10 10 7 10 10 9 10 9 10 9 8 8 5 10 10 8 9 10 9 7 Wheat 0 9 8 7 6 9 9 7 9 8 8 9 9 9 4 9 9 9 9 8 9 9 Wild buckwheat 0 9 9 10 10 9 9 9 10 9 9 9 9 10 10 9 9 9 10 9 10 9 Wild oat 0 9 8 7 7 9 9 7 8 9 9 9 9 9 9 9 9 9 9 9 9 10 Barnyardgrass 0 9 8 9 9 8 9 9 8 0 0 9 0 8 8 9 9 9 9 3 8 0 Rice Japonica 4 9 8 9 9 9 8 9 9 0 0 9 9 9 8 9 9 9 9 9 8 8 Umbrella sedge 0 10 9 9 9 9 9 9 9 0 6 6 5 8 8 9 9 5 9 4 5 5 COMPOUND Rate (62 g/ha) 269 270 271 274 275 276 289 292 300 301 302 305 310 Barley Igri 9 10 10 9 9 -- 10 7 10 10 10 9 9 Bedstraw 10 10 10 9 10 6 10 10 10 10 10 10 10 Blackgrass 10 10 10 9 10 9 10 10 10 10 10 10 10 Chickweed 2 8 10 0 10 1 10 9 10 10 10 10 7 Corn 9 10 10 10 10 8 10 10 9 10 10 10 9 Cotton 5 9 9 2 8 0 10 8 10 8 9 9 8 Crabgrass 0 10 10 5 10 3 8 9 9 9 10 10 4 Downy brome 9 10 10 9 9 -- 9 4 10 9 10 9 9 Duck salad 0 0 3 0 8 0 8 8 6 5 9 9 0 Giant foxtail 3 10 10 6 10 6 10 10 10 10 10 10 9 Lambsquarters 0 10 10 0 10 3 10 8 10 10 10 10 9 Morningglory 7 10 10 0 8 7 10 6 8 10 10 10 10 Pigweed 7 10 10 4 10 8 9 7 9 9 10 9 8 Rape 10 9 9 6 10 0 5 9 9 9 9 9 9 Ryegrass 5 9 10 9 10 2 8 7 10 9 10 9 9 Sorghum 8 10 10 9 10 8 10 10 9 10 10 10 9 Soybean 7 8 9 3 8 4 8 2 9 9 10 10 9 Speedwell 3 6 3 0 7 0 8 9 10 10 8 10 10 Sugar beet -- 9 9 7 9 5 10 9 9 10 10 10 10 Velvetleaf 4 9 10 3 7 4 7 7 8 7 10 8 9 Wheat 5 10 9 9 9 -- 9 8 9 9 9 9 6 Wild buckwheat 10 10 10 -- 10 0 9 -- 9 9 9 8 9 Wild oat 5 10 9 9 9 -- 9 8 10 10 10 9 9 Barnyardgrass 7 4 9 0 9 0 7 5 6 9 10 10 7 Rice Japonica 8 9 9 6 9 7 8 2 7 7 8 8 4 Umbrella sedge 7 10 9 3 9 0 8 3 9 9 9 8 3 COMPOUND Rate (62 g/ha) 1 2 3 5 7 11 13 14 35 50 51 53 58 59 60 63 64 71 77 78 81 82 83 84 86 88 89 102 103 PREEMERGENCE Barley Igri 8 9 6 7 2 0 3 0 3 8 9 9 7 7 4 9 9 2 6 5 9 6 6 8 9 6 8 8 9 Bedstraw 10 10 10 10 0 9 9 8 10 10 10 10 10 10 10 9 9 9 6 8 8 9 9 7 9 9 9 9 9 Blackgrass 9 10 9 9 6 8 8 6 8 9 9 10 8 8 8 10 10 7 8 8 9 10 10 9 9 9 9 10 10 Chickweed 7 10 10 10 0 10 10 10 10 10 10 10 10 10 10 9 10 8 7 8 8 10 10 8 9 10 10 9 9 Corn 4 9 10 7 0 4 9 3 6 2 10 7 8 8 7 10 10 5 2 8 -- -- -- 10 4 8 7 7 2 Cotton 4 4 7 8 0 4 9 3 7 8 10 9 5 9 9 9 9 9 4 8 -- -- -- 9 9 9 7 4 9 Crabgrass 7 8 9 8 3 6 4 0 8 9 10 10 7 7 6 10 9 6 6 8 -- -- -- 6 7 3 8 3 4 Downy brome 9 10 9 10 5 7 7 6 10 9 9 9 7 8 7 10 9 2 7 6 9 9 7 6 7 7 5 8 9 Duck salad -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Giant foxtail 5 9 9 7 4 8 3 2 9 8 9 10 6 4 3 9 9 0 6 9 -- -- -- 10 8 8 8 8 8 Lambsquarters 10 10 10 10 5 10 10 10 10 10 10 10 10 10 10 10 10 8 8 9 10 9 9 10 10 9 10 10 10 Morningglory 0 4 6 8 0 5 8 0 8 9 10 8 0 10 10 9 10 8 3 10 -- -- -- 9 9 7 9 8 9 Pigweed 9 10 9 10 6 8 9 8 8 10 10 10 10 9 9 9 10 9 9 9 -- -- -- 7 9 9 9 9 9 Rape 9 10 10 10 0 6 10 8 9 9 9 9 10 10 10 10 10 9 10 9 9 9 9 9 9 9 9 9 9 Ryegrass 9 6 3 10 3 8 7 4 10 9 9 10 8 10 8 10 10 6 5 8 9 6 9 9 7 6 8 1 2 Sorghum 9 9 9 9 6 9 9 6 9 9 10 9 10 10 8 9 ;10 7 8 10 -- -- -- 9 10 9 9 9 9 Soybean 4 7 6 7 0 3 8 3 3 8 10 8 5 9 9 10 9 9 6 9 -- -- -- 9 6 9 8 2 7 Speedwell 9 10 8 10 5 4 9 7 10 10 10 10 10 10 9 10 8 6 3 6 9 10 10 9 9 9 9 9 8 Sugar beet 9 10 10 10 0 9 9 9 10 9 9 9 10 10 10 10 10 9 9 9 9 9 9 9 9 9 9 9 9 Velvetleaf 7 9 7 9 3 8 8 0 8 9 9 9 8 10 8 9 9 9 7 8 -- -- -- 8 8 7 9 7 9 Wheat 9 10 8 9 2 0 0 2 4 8 9 9 0 6 4 9 9 3 5 4 8 8 8 9 5 5 8 6 8 Wild buckwheat 10 10 10 10 0 7 8 8 9 9 9 9 8 9 8 9 8 6 8 8 9 9 9 6 9 9 9 9 9 Wild oat 4 7 5 4 2 0 0 0 5 7 9 9 4 6 7 7 8 0 2 3 8 5 7 9 3 0 3 4 7 Barnyardgrass -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Rice Japonica -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Umbrella sedge -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- --
TABLE B - COMPOUND Rate (62 g/ha) 108 109 110 111 112 114 115 116 117 118 119 120 121 122 125 166 167 170 172 173 203 208 PREEMERGENCE Barley Igri 9 9 9 5 5 8 2 9 4 2 10 9 9 9 0 7 0 2 5 0 9 9 Bedstraw 10 10 10 10 10 9 9 9 9 9 9 9 10 10 8 9 9 10 8 8 8 10 Blackgrass 10 10 10 10 10 9 9 9 8 8 10 10 10 10 9 9 9 9 10 9 9 9 Chickweed 10 9 9 9 9 10 8 10 9 9 10 10 10 10 9 9 9 10 9 8 9 9 Corn 10 8 9 5 6 9 9 9 6 6 9 9 10 10 0 9 10 10 4 9 9 10 Cotton 10 9 10 8 9 6 5 9 10 5 10 8 10 10 3 7 3 9 6 8 8 8 Crabgrass 10 9 9 7 7 8 5 9 7 3 7 6 8 7 3 9 8 9 9 9 8 10 Downy brome 9 9 9 9 9 8 5 8 7 4 10 9 10 10 0 9 9 6 4 8 10 9 Duck salad -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Giant foxtail 9 9 9 9 7 9 7 8 6 5 8 8 8 6 0 9 8 9 9 9 4 9 Lambsquarters 10 9 10 9 9 9 8 10 9 9 10 10 10 9 10 10 10 10 10 10 9 10 Morningglory 10 8 9 7 9 9 9 9 10 7 9 9 9 9 5 7 5 9 6 5 8 9 Pigweed 10 9 10 10 9 9 9 9 9 8 9 9 10 9 9 9 8 9 9 9 9 10 Rape 10 9 9 9 9 9 9 10 9 10 10 10 10 10 9 9 9 10 3 7 10 10 Ryegrass 10 10 9 8 9 9 5 9 8 8 10 9 10 10 2 9 9 9 5 9 9 10 Sorghum 10 9 9 10 10 9 9 9 9 5 9 9 10 10 0 9 9 9 6 9 10 10 Soybean 10 8 10 6 5 7 4 9 9 1 9 8 10 10 2 7 3 9 6 8 7 8 Speedwell 7 9 10 9 10 10 10 10 8 10 10 10 10 5 10 10 8 10 10 10 8 9 Sugar beet 10 10 9 9 9 9 9 9 9 9 10 10 10 10 9 10 10 10 10 9 9 9 Velvetleaf 9 9 10 9 10 9 8 9 9 7 9 9 10 9 7 8 7 9 6 7 9 10 Wheat 9 9 7 5 4 6 1 4 3 0 9 9 9 9 0 8 4 9 7 0 9 9 Wild buckwheat 9 9 9 10 9 9 9 9 9 10 10 10 10 10 9 7 9 8 10 10 9 9 Wild oat 9 9 9 0 5 7 3 8 7 3 9 6 9 9 0 5 5 5 4 0 6 7 Barnyardgrass -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Rice Japonica -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Umbrella sedge -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- COMPOUND Rate (62 g/ha) 209 211 212 213 214 217 218 219 225 229 230 231 232 252 254 256 258 259 261 266 267 268 PREEMERGENCE Barley Igri 0 6 3 8 9 9 8 2 7 9 5 9 9 2 7 9 8 6 9 3 9 9 Bedstraw 3 10 10 10 10 9 9 10 9 9 9 10 10 9 10 10 10 9 10 9 10 10 Blackgrass 0 9 9 9 8 9 9 8 5 9 9 9 9 10 9 10 10 10 10 10 10 10 Chickweed 3 10 10 10 9 10 10 10 8 9 9 9 2 10 10 6 10 9 9 8 10 10 Corn 0 10 9 10 10 9 8 0 10 6 3 9 9 8 10 9 10 10 9 7 10 9 Cotton 0 8 6 10 10 7 7 10 9 3 -- 9 8 3 9 10 8 8 9 6 9 9 Crabgrass 0 10 8 9 7 6 8 0 3 4 7 7 7 4 6 8 9 8 9 5 7 6 Downy brome 5 9 8 9 9 9 9 8 -- 7 7 10 10 10 9 10 10 10 10 9 10 10 Duck salad -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Giant foxtail 0 10 8 9 4 5 7 0 5 10 6 7 6 6 6 8 9 9 9 4 6 6 Lambsquarters 0 9 9 10 10 10 10 8 -- 10 6 9 10 9 8 10 10 10 10 9 10 9 Morningglory 0 4 6 10 10 3 5 3 9 4 2 9 9 0 9 9 7 5 9 8 9 9 Pigweed 0 10 9 10 10 8 9 7 9 9 8 9 10 7 9 8 9 9 10 7 9 9 Rape 0 9 9 10 10 9 5 9 8 0 3 3 5 9 10 9 9 9 9 7 9 9 Ryegrass 3 8 4 9 7 8 6 7 0 2 0 9 8 5 9 10 10 9 10 3 9 6 Sorghum 3 10 9 10 10 10 9 4 9 9 9 10 9 9 9 10 9 9 10 9 10 9 Soybean 0 7 6 10 10 5 6 4 9 6 6 9 8 6 9 8 7 6 7 6 8 8 Speedwell 0 10 10 10 8 10 9 2 -- 9 9 9 0 10 9 9 7 8 9 9 10 8 Sugar beet 4 9 9 10 10 9 9 10 8 8 5 9 9 8 9 9 9 9 9 5 9 9 Velvetleaf 0 8 5 10 7 8 8 5 9 9 4 9 5 5 7 9 9 7 7 8 8 3 Wheat 0 7 3 9 5 9 7 0 3 8 5 9 9 0 0 9 8 9 8 3 9 6 Wild buckwheat 3 9 9 9 9 8 9 9 9 8 9 9 8 9 9 9 9 9 9 10 9 9 Wild oat 0 5 2 7 6 7 5 4 4 6 2 9 8 2 8 9 9 9 9 5 6 5 Barnyardgrass -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Rice Japonica -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Umbrella sedge -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- COMPOUND Rate (62 g/ha) 269 270 271 274 275 276 289 292 300 301 302 305 310 PREEMERGENCE Barley Igri 0 9 9 2 10 0 5 0 4 5 9 9 0 Bedstraw 6 9 9 0 10 0 9 0 4 8 10 9 8 Blackgrass 9 10 10 9 10 5 9 0 9 9 10 10 9 Chickweed 0 0 10 0 10 3 9 5 7 9 10 10 9 Corn 0 9 7 0 10 0 6 0 5 2 3 7 4 Cotton 0 9 8 0 9 0 0 0 4 8 9 8 9 Crabgrass 1 9 9 3 10 0 2 2 5 7 9 7 0 Downy brome 3 10 10 9 10 0 7 0 8 9 10 9 0 Duck salad -- -- -- -- -- -- -- -- -- -- -- -- -- Giant foxtail 0 9 9 5 9 3 7 0 8 7 9 9 0 Lambsquarters 9 9 10 0 10 0 0 0 9 10 10 10 10 Morningglory 0 3 9 0 5 0 0 0 7 7 9 7 7 Pigweed 7 9 9 5 9 3 9 0 9 9 9 9 8 Rape 2 9 8 0 9 0 1 0 6 6 10 4 3 Ryegrass 0 9 9 0 10 0 6 0 4 5 10 7 2 Sorghum 2 9 9 4 10 8 9 1 6 5 9 9 0 Soybean 0 3 4 0 6 0 0 0 3 3 6 5 5 Speedwell 9 9 9 0 10 6 10 -- 8 10 10 10 10 Sugar beet -- 10 10 0 10 0 9 4 9 9 10 10 10 Velvetleaf 1 5 4 3 3 5 4 0 6 6 9 6 8 Wheat 0 9 9 7 10 0 1 0 6 6 9 5 0 Wild buckwheat 9 9 9 -- 10 3 8 5 4 8 10 9 9 Wild oat 0 9 9 0 9 0 5 0 4 5 9 6 0 Barnyardgrass -- -- -- -- -- -- -- -- -- -- -- -- -- Rice Japonica -- -- -- -- -- -- -- -- -- -- -- -- -- Umbrella sedge -- -- -- -- -- -- -- -- -- -- -- -- -- COMPOUND Rate (31 g/ha) 1 2 3 5 7 11 13 14 25 26 27 28 29 30 31 34 35 36 50 51 53 58 59 60 63 64 71 77 78 POSTEMERGENCE Barley Igri 10 9 9 10 7 9 9 9 9 8 10 9 10 10 9 7 5 5 8 9 9 5 7 5 9 9 2 2 1 Bedstraw 10 10 10 10 3 8 9 8 10 10 10 10 10 10 7 8 10 10 8 10 9 10 10 10 7 9 7 5 7 Blackgrass 9 9 9 10 7 9 8 7 10 10 10 10 10 10 9 8 9 10 9 9 9 9 8 8 9 9 4 7 7 Chickweed 6 8 9 10 0 10 9 9 10 10 10 10 10 10 4 10 10 10 9 10 9 9 10 10 10 10 9 4 9 Corn 7 10 10 10 6 10 10 10 10 10 10 10 10 10 10 10 10 10 7 10 7 10 10 8 10 10 6 6 7 Cotton 6 7 8 7 4 8 7 9 5 7 10 10 10 10 6 6 7 8 10 10 10 9 10 10 9 9 10 6 7 Crabgrass 7 6 7 8 5 6 10 7 7 6 10 6 10 10 6 7 4 7 4 7 7 3 0 0 5 8 6 5 4 Downy brome 9 8 8 10 6 9 5 5 10 9 10 10 10 10 5 7 9 10 8 8 9 5 7 6 9 8 1 5 2 Duck salad -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- 10 9 10 7 10 10 9 9 9 7 6 Giant foxtail 7 8 9 10 6 10 10 10 10 10 10 9 10 10 9 8 8 10 10 10 8 7 5 3 10 10 5 7 7 Lambsquarters 10 10 10 10 -- 10 10 8 10 10 10 10 10 10 10 10 10 10 10 10 10 9 10 10 10 10 8 9 10 Morningglory 7 10 10 8 6 8 8 9 10 10 10 10 10 10 8 8 10 10 10 10 10 10 10 10 10 10 10 9 10 Pigweed 6 6 6 10 3 8 9 3 10 10 10 10 10 10 7 8 8 10 10 10 10 10 10 10 10 10 10 9 10 Rape 6 8 10 10 0 10 10 10 9 10 10 10 10 10 0 5 4 10 10 10 10 10 10 10 10 10 7 8 9 Ryegrass 10 9 4 10 4 9 8 5 10 10 10 10 10 10 9 9 9 10 9 10 9 5 9 8 8 9 3 4 4 Sorghum 7 10 10 10 7 10 10 10 10 10 10 10 10 10 10 7 10 10 7 10 6 7 7 7 10 10 6 8 10 Soybean 7 10 10 10 3 8 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 9 9 9 Speedwell 5 6 4 9 0 0 6 0 8 6 6 9 9 0 0 0 5 8 6 10 8 9 10 8 -- 4 1 4 6 Sugar beet 10 10 10 10 6 10 10 9 10 10 10 10 10 10 10 10 10 10 10 10 10 9 10 10 10 10 9 10 10 Velvetleaf 7 8 10 9 4 8 9 6 7 9 10 10 10 10 7 6 7 10 10 10 10 10 10 7 10 10 9 8 10 Wheat 7 8 8 10 5 9 9 9 9 9 10 9 10 10 8 6 7 8 9 9 9 4 5 2 9 9 0 2 1 Wild buckwheat 10 7 9 10 0 9 5 7 10 7 10 10 10 10 6 0 0 5 7 10 8 8 10 10 9 9 0 4 8 Wild oat 10 10 9 9 5 9 7 6 10 9 9 9 9 -- 9 8 9 9 7 9 7 4 7 5 7 7 0 0 2 Barnyardgrass 2 6 5 8 0 7 8 7 8 8 8 9 10 8 3 2 8 9 8 9 9 8 8 7 9 9 8 6 8 Rice Japonica 8 8 8 9 0 8 8 7 7 8 8 8 9 8 6 8 8 8 0 9 9 8 9 9 8 9 8 7 9 Umbrella sedge 8 9 9 8 4 8 4 2 9 9 9 10 9 8 8 2 3 8 9 10 9 8 9 9 9 9 3 9 9 COMPOUND Rate (31 g/ha) 81 82 83 84 86 88 89 102 103 107 108 109 110 111 112 114 1 15 116 117 118 119 120 121 122 POSTEMERGENCE Barley Igri 7 7 8 7 6 6 7 9 9 9 7 10 10 9 8 6 4 6 3 3 10 8 10 10 Bedstraw 6 9 10 9 10 10 10 9 9 10 10 9 10 10 10 10 10 10 10 9 9 10 10 10 Blackgrass 10 10 10 9 9 9 10 9 9 10 9 10 10 10 10 9 9 9 8 9 10 10 9 10 Chickweed 9 10 10 10 6 9 10 9 9 10 10 10 10 10 9 9 5 10 10 3 10 10 10 10 Corn 0 7 9 10 1 7 9 3 0 10 10 9 10 10 8 9 9 8 4 3 10 10 10 10 Cotton 7 9 9 9 8 8 9 7 8 10 10 9 9 10 8 8 9 9 9 3 10 10 10 10 Crabgrass 4 4 5 4 2 0 2 0 2 7 5 6 9 0 2 0 0 2 0 0 7 4 7 5 Downy brome 6 6 3 8 4 6 4 8 8 9 9 9 10 9 6 6 0 7 0 0 10 9 9 9 Duck salad 3 9 9 1 9 6 9 3 7 10 10 9 10 8 9 4 4 7 5 4 9 9 9 9 Giant foxtail 8 8 9 8 5 5 5 6 6 9 5 9 9 8 4 8 5 6 2 0 9 9 10 4 Lambsquarters 8 9 10 10 9 9 10 9 10 10 10 10 10 10 10 8 5 7 5 0 10 10 10 10 Morningglory 9 10 10 8 9 10 10 9 9 10 10 7 10 10 10 8 10 10 10 9 10 10 10 10 Pigweed 9 10 10 9 8 7 5 8 10 10 10 10 10 10 10 7 6 9 8 0 10 10 10 10 Rape 9 10 10 10 10 10 10 9 9 10 10 10 10 10 10 9 9 10 9 10 10 10 10 10 Ryegrass 5 5 5 8 4 6 4 5 3 10 10 10 10 9 7 8 5 9 6 5 10 5 10 10 Sorghum 10 10 10 10 9 8 9 9 10 10 10 9 10 10 9 8 9 9 9 0 10 10 10 9 Soybean 8 9 9 9 8 9 9 7 9 10 10 8 10 10 9 8 9 9 9 0 10 10 10 10 Speedwell 3 6 0 10 7 9 9 -- -- -- -- 10 10 -- 10 9 5 10 9 -- 9 0 10 -- Sugar beet 9 9 10 10 9 9 9 9 10 10 10 9 10 10 10 6 8 9 9 5 10 10 10 10 Velvetleaf 8 9 10 7 8 7 8 4 9 10 8 10 10 10 10 8 9 9 9 4 10 10 10 8 Wheat 4 4 3 9 4 5 6 9 9 9 4 9 9 8 5 5 4 2 0 0 9 8 9 9 Wild buckwheat 9 8 9 9 8 9 9 9 9 10 10 -- 9 9 9 9 -- 9 9 -- 10 10 8 9 Wild oat 7 4 2 9 3 4 2 8 8 9 9 9 10 7 6 6 4 8 5 3 9 6 9 9 Barnyardgrass 8 9 9 3 9 8 8 2 6 8 9 9 9 8 8 8 9 8 5 7 9 8 9 8 Rice Japonica 8 9 9 8 8 7 6 3 3 9 9 9 9 8 8 8 7 7 8 6 8 8 9 8 Umbrella sedge 8 8 9 4 8 6 7 3 9 9 8 8 9 8 8 8 9 9 9 8 9 8 9 9 COMPOUND Rate (31 g/ha) 125 166 167 170 172 173 203 204 205 206 207 208 209 211 212 213 214 217 218 219 225 229 POSTEMERGENCE Barley Igri 0 9 9 8 9 9 9 10 10 10 9 9 0 10 9 6 6 9 8 6 9 9 Bedstraw 3 9 10 10 9 10 9 9 10 10 10 10 0 9 10 10 10 7 8 10 8 10 Blackgrass 6 9 9 9 10 10 9 10 10 10 10 10 5 10 9 8 8 9 7 7 7 10 Chickweed 7 10 10 10 8 8 9 10 10 10 10 9 0 9 7 10 10 8 10 10 10 9 Corn 4 10 10 10 9 9 10 10 10 10 10 10 3 10 10 10 10 10 9 10 10 9 Cotton 8 8 8 10 5 9 9 5 8 8 6 9 0 9 9 10 10 6 7 7 8 0 Crabgrass 0 7 4 10 8 9 10 10 10 10 10 10 0 6 6 6 4 7 4 3 8 4 Downy brome 0 8 9 8 9 9 10 10 10 10 10 9 0 10 9 8 7 9 7 6 9 9 Duck salad 3 9 7 9 5 4 9 9 10 9 10 10 0 10 9 9 9 6 4 0 2 4 Giant foxtail 0 9 7 10 9 9 6 10 10 10 10 10 5 10 9 8 6 8 6 3 10 8 Lambsquarters 10 10 10 10 9 9 10 10 10 10 10 10 0 10 10 10 10 10 10 10 10 10 Morningglory 10 9 10 10 9 10 10 10 10 9 8 10 3 10 10 10 10 10 10 10 9 9 Pigweed 8 10 8 10 9 9 10 10 10 10 9 10 0 10 7 10 10 10 7 9 10 8 Rape 9 10 10 10 5 9 10 10 10 10 9 10 0 9 9 10 10 9 9 9 10 8 Ryegrass 0 9 9 9 9 9 10 10 10 10 -- 10 0 9 7 10 7 9 7 8 9 5 Sorghum 4 10 10 10 6 9 10 10 10 10 10 10 6 9 10 10 10 10 8 7 10 8 Soybean 8 9 10 10 9 9 8 10 10 10 10 8 0 10 9 10 10 8 10 10 10 9 Speedwell 0 8 5 9 9 6 7 8 4 9 0 7 0 8 1 10 7 3 0 3 6 6 Sugar beet 10 10 10 10 9 9 10 10 10 10 10 10 0 8 8 10 10 9 9 10 10 8 Velvetleaf 9 9 9 10 8 8 10 10 10 9 8 10 0 10 10 9 6 10 8 8 10 9 Wheat 0 9 9 9 9 9 9 9 9 9 9 9 0 9 8 6 4 9 9 6 7 8 Wild buckwheat 8 8 9 9 9 9 9 9 10 10 9 9 0 8 9 10 10 8 8 8 10 9 Wild oat 0 9 9 9 9 9 9 10 10 9 9 8 0 8 7 7 6 9 7 6 7 9 Barnyardgrass 3 8 0 9 3 4 5 9 9 9 9 10 0 9 8 9 8 8 8 8 5 0 Rice Japonica 3 8 6 9 3 9 9 9 9 9 9 9 3 9 8 9 9 8 8 8 8 0 Umbrella sedge 9 10 9 8 7 8 9 9 9 9 9 9 0 9 9 9 9 9 9 9 9 0 COMPOUND Rate (31 g/ha) 230 231 232 240 241 242 243 244 245 252 254 256 258 259 261 266 267 268 269 270 271 272 POSTEMERGENCE Barley Igri 9 9 8 10 10 10 10 10 10 9 7 9 9 9 10 9 9 9 8 -- 10 9 Bedstraw 9 10 10 10 10 10 10 10 10 10 10 10 9 9 10 10 10 10 9 10 10 10 Blackgrass 9 9 10 10 10 10 10 10 10 10 9 9 9 9 9 10 10 10 9 10 10 10 Chickweed 9 10 10 10 10 10 10 10 5 5 10 8 10 8 9 3 9 10 0 7 10 10 Corn 9 10 10 10 10 10 10 10 10 10 9 10 10 10 10 10 10 10 9 10 10 10 Cotton 1 8 6 9 9 10 10 10 8 7 8 0 3 7 4 4 8 8 5 9 8 6 Crabgrass 1 7 7 9 9 10 10 10 9 7 0 9 10 4 7 0 3 2 0 10 10 9 Downy brome 8 9 10 10 10 10 10 10 9 10 8 9 9 10 9 9 10 10 8 8 10 9 Duck salad 6 0 0 7 8 9 8 8 9 0 3 3 6 4 4 8 3 3 0 0 0 0 Giant foxtail 7 7 7 9 10 10 10 10 10 9 5 10 10 10 10 10 5 5 2 10 10 10 Lambsquarters 10 10 10 10 10 10 10 9 9 4 2 10 10 10 10 8 10 0 0 -- 10 10 Morningglory 10 9 8 10 10 10 10 10 10 10 10 10 10 8 10 10 10 10 5 9 10 10 Pigweed 9 10 8 10 10 10 10 10 10 8 9 10 10 10 9 3 10 9 7 10 10 10 Rape 9 9 7 10 10 10 10 10 10 9 10 10 10 9 10 9 10 9 9 9 9 9 Ryegrass 0 9 9 10 10 10 10 10 10 5 7 10 9 10 10 0 10 10 5 8 10 10 Sorghum 8 10 10 10 10 10 10 10 10 10 8 10 10 10 10 10 10 10 8 10 10 10 Soybean 8 9 9 9 10 9 9 9 10 8 10 7 10 9 8 10 10 10 5 7 8 7 Speedwell 0 -- 10 4 4 9 10 0 8 5 3 2 0 2 2 2 10 0 0 5 0 0 Sugar beet 8 9 9 10 10 10 10 10 10 8 9 8 9 9 9 6 10 10 2 9 9 9 Velvetleaf 10 9 7 8 8 10 10 10 9 7 4 9 10 7 5 10 8 6 2 9 7 9 Wheat 6 9 9 9 9 10 10 9 9 9 3 8 9 9 8 8 9 8 4 9 9 9 Wild buckwheat 9 9 9 10 10 -- 9 -- 10 10 10 9 9 8 10 9 9 9 10 10 10 -- Wild oat 9 9 9 10 10 10 10 10 9 7 9 9 9 9 8 9 9 9 5 9 9 9 Barnyardgrass 0 6 0 7 7 9 9 9 9 3 7 6 9 9 9 0 3 0 6 0 3 5 Rice Japonica 0 8 8 9 9 9 9 9 8 8 8 9 9 8 9 1 8 8 6 9 8 8 Umbrella sedge 3 4 0 9 9 9 8 9 9 8 7 9 9 5 9 3 5 4 2 9 9 9
TABLE B - COMPOUND Rate (31 g/ha) 274 275 276 283 284 285 286 287 288 289 291 292 300 301 302 305 310 POSTEMERGENCE Barley Igri 3 9 7 10 10 10 10 10 10 9 10 5 10 10 10 9 9 Bedstraw 2 10 6 10 10 10 10 10 10 10 10 8 10 10 10 10 10 Blackgrass 9 10 9 10 10 10 10 10 10 10 10 9 10 10 10 10 9 Chickweed 0 10 1 10 10 10 10 10 10 10 10 8 10 10 10 10 6 Corn 9 10 8 10 10 10 10 10 10 10 10 10 9 10 10 10 9 Cotton 0 7 0 10 10 10 10 10 7 8 8 7 7 7 9 8 7 Crabgrass 5 10 2 9 8 8 10 10 7 8 10 5 9 8 10 10 4 Downy brome 6 9 -- 10 10 10 10 10 9 9 10 3 10 9 10 9 9 Duck salad 0 7 0 9 9 8 9 9 9 7 8 2 5 4 8 7 0 Giant foxtail 5 10 5 10 10 10 10 10 10 9 10 7 10 10 10 10 9 Lambsquarters 0 9 0 10 10 10 10 10 10 9 10 8 10 10 10 10 9 Morningglory 0 7 7 9 10 10 10 10 10 9 9 5 7 9 10 10 10 Pigweed 4 10 7 10 10 10 10 10 9 9 10 7 8 9 10 8 7 Rape 0 9 0 10 10 10 10 10 10 3 10 9 9 9 9 9 9 Ryegrass 0 10 2 10 8 4 10 10 7 6 10 5 10 9 10 9 7 Sorghum 9 10 8 10 10 10 10 10 10 10 10 10 9 10 10 10 9 Soybean 2 7 3 9 10 10 10 10 10 8 9 1 9 9 10 9 9 Speedwell 0 6 0 8 8 0 10 2 10 6 0 8 10 10 6 10 10 Sugar beet 5 9 2 9 9 9 10 10 10 9 9 9 9 10 10 10 10 Velvetleaf 0 6 4 9 10 10 10 7 10 6 8 5 6 7 9 7 9 Wheat 6 9 5 9 9 9 10 9 9 9 9 6 9 9 9 9 5 Wild buckwheat 6 10 -- 10 10 10 10 10 10 -- -- -- 9 8 9 -- 8 Wild oat 4 9 -- 10 9 9 9 10 9 8 9 5 10 10 10 8 9 Barnyardgrass 0 9 0 9 7 5 9 9 9 3 8 3 5 9 10 9 3 Rice Japonica 3 9 3 9 8 7 9 9 8 0 8 2 6 6 8 8 2 Umbrella sedge 0 9 0 9 9 9 9 9 9 8 9 0 9 7 9 7 2 COMPOUND Rate (31 g/ha) 1 2 3 5 7 11 13 14 25 26 27 28 29 30 31 34 35 36 50 51 53 58 59 60 63 64 71 77 78 PREEMERGENCE Barley Igri 5 7 6 6 0 0 0 0 2 1 2 2 2 0 2 0 0 2 6 9 9 3 7 3 9 9 0 4 5 Bedstraw 9 10 10 10 0 5 8 8 8 8 8 9 9 10 8 9 9 10 9 10 10 10 10 10 9 9 9 2 8 Blackgrass 8 8 9 7 4 7 7 4 8 8 9 8 9 7 4 4 7 8 9 9 10 8 8 7 9 9 6 8 7 Chickweed 6 10 10 10 0 10 8 10 8 9 9 8 9 10 0 8 10 10 10 10 10 9 10 10 9 9 8 5 7 Corn 0 8 8 6 0 4 8 3 9 9 9 10 10 10 8 0 2 3 0 10 6 7 7 4 9 10 0 0 6 Cotton 3 3 6 7 0 4 9 3 6 7 8 5 9 9 2 0 7 9 8 10 8 4 9 9 8 9 7 0 7 Crabgrass 3 8 7 7 0 2 2 0 8 10 9 8 9 9 7 7 4 8 8 10 9 6 7 3 9 9 3 3 6 Downy brome 8 9 6 10 4 3 6 3 4 3 4 7 7 9 1 0 8 8 8 9 9 6 7 7 10 8 2 6 4 Duck salad -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Giant foxtail 3 8 8 4 3 5 3 2 7 9 9 7 9 9 8 6 7 9 8 8 9 6 3 0 9 9 0 5 7 Lambsquarters 9 10 10 10 5 10 9 10 3 9 10 5 9 8 5 6 10 10 10 10 10 9 10 10 10 10 8 6 7 Morningglory 0 3 5 8 0 2 6 0 6 7 2 7 9 9 5 2 3 8 9 10 5 0 10 10 9 10 8 2 9 Pigweed 7 10 7 10 6 7 9 8 9 9 8 8 9 10 7 8 8 9 10 10 10 9 9 9 9 10 9 9 9 Rape 6 10 9 10 0 4 9 8 6 4 8 9 8 8 3 0 6 8 9 9 9 10 10 10 10 10 9 9 9 Ryegrass 6 4 2 8 0 5 7 3 5 8 5 9 4 8 3 0 6 7 9 9 10 7 10 8 10 9 6 5 8 Sorghum 7 8 9 9 4 8 9 5 10 10 9 9 10 10 7 5 9 9 8 10 9 10 10 8 9 10 7 7 10 Soybean 4 5 4 7 0 2 3 2 3 5 4 4 9 8 2 2 2 6 7 10 7 4 8 8 9 9 8 4 7 Speedwell 7 10 5 10 0 4 8 7 8 8 2 8 9 3 0 6 10 8 9 10 10 10 10 9 9 8 5 0 2 Sugar beet 8 10 10 10 0 9 8 8 9 9 8 8 9 10 2 9 10 10 9 9 9 10 10 10 10 10 9 9 9 Velvetleaf 6 7 5 8 0 4 8 0 7 7 8 7 9 8 3 0 5 8 8 9 8 8 10 8 9 9 9 4 7 Wheat 6 8 7 8 0 0 0 2 4 4 0 2 3 1 2 0 3 0 5 9 9 0 5 3 9 9 2 3 4 Wild buckwheat 9 10 10 10 0 6 8 7 7 7 7 8 9 8 0 0 9 10 -- 9 9 8 9 8 9 8 5 6 7 Wild oat 3 5 3 3 0 0 0 0 5 4 0 3 4 3 2 3 4 3 5 9 8 3 6 6 6 5 0 0 1 Barnyardgrass -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Rice Japonica -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Umbrella sedge -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- COMPOUND Rate (31 g/ha) 81 82 83 84 86 88 89 102 103 107 108 109 110 111 112 114 1 15 116 117 118 119 120 121 122 PREEMERGENCE Barley Igri 8 6 4 3 6 6 6 7 8 9 9 9 9 3 4 6 0 8 4 0 9 6 9 9 Bedstraw 7 9 9 0 9 9 9 9 9 10 10 10 10 9 10 9 9 9 9 9 9 7 10 10 Blackgrass 9 9 10 8 9 9 9 9 9 10 10 10 10 10 9 9 9 9 8 7 10 10 10 10 Chickweed 7 10 10 7 9 9 9 9 9 10 9 9 9 9 9 9 8 9 9 8 10 10 10 10 Corn -- -- -- 10 4 6 7 7 0 10 10 7 8 3 5 9 6 8 5 4 9 8 10 9 Cotton -- -- -- 8 9 9 7 4 9 10 10 9 10 6 8 4 2 9 9 5 9 8 10 10 Crabgrass -- -- -- 6 7 2 5 0 3 9 9 8 9 4 4 7 3 8 6 2 7 6 5 7 Downy brome 8 7 5 -- 6 6 5 5 8 9 8 9 9 6 6 7 3 7 5 3 10 7 10 10 Duck salad -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Giant foxtail -- -- -- 6 8 5 7 7 7 9 8 8 9 7 5 9 5 8 5 1 8 7 5 5 Lambsquarters 9 9 9 9 10 8 10 10 10 10 10 9 10 9 9 9 8 9 9 9 10 10 10 9 Morningglory -- -- -- 7 8 5 9 8 9 10 10 7 8 7 9 8 7 9 10 6 9 9 9 9 Pigweed -- -- -- 7 8 8 9 9 9 10 10 9 10 10 9 9 9 9 9 7 9 9 9 9 Rape 9 9 9 3 9 9 9 9 9 10 10 9 9 9 9 9 9 9 9 6 10 10 10 10 Ryegrass 6 5 5 4 5 6 8 1 2 10 10 10 9 7 9 8 5 9 7 6 10 5 10 10 Sorghum -- -- -- 9 9 9 9 9 9 9 10 9 9 4 10 9 9 9 9 3 9 9 10 10 Soybean -- -- -- 8 6 7 8 0 6 10 9 8 9 6 5 6 2 8 8 0 8 7 10 10 Speedwell 9 10 10 9 9 9 9 9 8 10 7 9 10 8 10 9 8 10 8 10 10 10 10 5 Sugar beet 9 9 9 4 9 9 9 9 9 10 10 9 9 9 9 9 7 9 9 8 10 10 10 10 Velvetleaf -- -- -- 7 8 6 8 7 8 10 9 9 9 7 9 7 7 9 9 2 9 9 9 9 Wheat 7 5 3 4 3 4 4 4 7 9 6 9 7 5 4 3 0 1 0 0 9 6 9 9 Wild buckwheat 9 9 8 5 9 9 8 9 9 9 9 -- 7 10 -- 9 9 9 9 9 10 10 9 10 Wild oat 7 4 2 6 2 0 3 4 5 9 9 9 8 0 0 5 0 8 5 0 8 4 9 9 Barnyardgrass -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Rice Japonica -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Umbrella sedge -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- COMPOUND Rate (31 g/ha) 125 166 167 170 172 173 203 204 205 206 207 208 209 211 212 213 214 217 218 219 225 229 PREEMERGENCE Barley Igri 0 6 0 0 2 0 8 8 9 9 7 9 0 4 0 7 6 6 6 0 5 9 Bedstraw 5 9 9 9 4 6 7 10 10 10 9 9 0 9 8 10 10 8 8 9 9 8 Blackgrass 5 8 9 7 9 9 8 9 9 9 9 9 0 8 9 9 8 9 9 6 5 9 Chickweed 8 9 9 9 6 -- 9 9 9 9 9 9 0 9 10 10 9 9 10 9 7 7 Corn 0 9 9 10 3 5 4 8 10 10 10 9 0 8 5 10 10 4 5 0 7 4 Cotton 0 7 0 9 4 6 7 8 9 9 8 -- 0 6 5 10 10 5 7 7 9 2 Crabgrass 2 9 8 9 7 8 8 10 10 9 9 10 0 9 7 8 6 5 5 0 2 3 Downy brome 0 8 5 6 4 5 9 9 9 10 9 9 3 8 6 9 8 9 9 7 5 7 Duck salad -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Giant foxtail 0 9 4 9 7 9 3 10 9 9 9 9 0 9 7 8 3 4 4 0 3 7 Lambsquarters 9 8 10 10 10 9 9 9 10 10 9 9 0 9 -- 10 10 -- 10 8 -- 9 Morningglory 3 5 5 8 5 2 6 7 9 8 8 9 0 3 5 10 9 3 4 2 9 2 Pigweed 8 9 8 9 9 9 9 10 10 10 9 10 0 10 6 10 9 7 8 6 7 9 Rape 8 9 7 10 3 2 10 10 9 9 9 10 0 9 6 10 10 8 4 6 5 0 Ryegrass 0 9 5 9 5 6 8 8 9 9 9 9 0 5 0 9 7 6 6 5 0 2 Sorghum 0 9 9 9 5 6 9 10 10 10 10 10 2 10 6 10 8 9 6 2 9 8 Soybean 0 5 2 8 3 5 6 7 7 7 8 7 0 6 4 10 9 3 6 2 7 4 Speedwell 9 10 -- 10 9 9 7 8 8 9 3 9 0 9 10 10 8 9 -- 0 9 8 Sugar beet 9 10 9 10 9 9 9 10 10 9 9 9 4 9 6 10 10 9 9 9 -- 5 Velvetleaf 5 7 6 9 6 4 9 8 9 9 9 9 0 7 3 10 7 7 5 2 9 7 Wheat 0 7 0 9 4 0 9 8 9 9 9 9 0 7 0 9 4 5 6 0 -- 7 Wild buckwheat 9 -- 7 8 9 9 9 9 9 9 8 9 3 9 5 9 9 6 8 8 9 4 Wild oat 0 4 2 2 0 0 6 6 7 8 7 7 0 3 0 6 5 5 3 2 2 2 Barnyardgrass -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Rice Japonica -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Umbrella sedge -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- COMPOUND Rate (31 g/ha) 230 231 232 240 241 242 243 244 245 252 254 256 258 259 261 266 267 268 269 270 271 272 PREEMERGENCE Barley Igri 0 9 9 9 9 6 9 8 9 0 5 9 8 4 9 1 9 5 0 6 9 2 Bedstraw 5 10 10 10 10 10 10 10 10 9 9 9 10 6 10 8 10 10 2 8 8 8 Blackgrass 9 9 9 10 10 10 10 10 10 10 9 10 10 10 10 10 10 10 9 10 10 10 Chickweed 5 5 0 9 10 9 9 10 9 9 9 6 10 9 9 6 7 9 0 0 10 10 Corn 2 4 5 9 9 9 10 10 9 8 4 9 10 10 9 5 5 3 0 9 4 2 Cotton 2 9 5 6 5 6 10 9 6 0 9 5 8 7 9 3 8 8 0 8 3 7 Crabgrass 5 7 5 9 9 9 7 9 8 2 6 7 8 7 7 5 7 5 0 8 9 10 Downy brome 4 9 10 10 10 9 10 10 10 8 9 9 8 10 10 7 10 10 -- 8 10 10 Duck salad -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Giant foxtail 4 6 4 8 9 9 7 9 8 3 5 7 8 7 8 4 6 3 0 5 9 9 Lambsquarters -- 9 9 10 10 9 10 9 10 7 8 9 10 10 9 9 9 9 9 8 8 7 Morningglory 0 9 8 7 7 6 9 9 8 0 9 5 7 2 8 8 8 9 0 2 6 0 Pigweed 5 8 9 9 9 10 10 10 9 5 8 7 9 9 9 7 9 8 5 9 9 10 Rape 3 0 0 9 9 9 10 10 10 8 10 9 8 4 9 4 6 9 0 5 8 8 Ryegrass 0 8 7 10 10 9 10 10 10 3 7 9 9 9 9 0 6 4 0 4 6 8 Sorghum 7 10 9 9 9 9 10 10 10 3 9 10 9 9 10 9 9 9 2 5 9 6 Soybean 2 8 7 7 9 7 9 10 7 4 8 7 7 5 5 5 7 8 0 2 2 0 Speedwell 5 6 0 10 10 8 10 0 10 10 8 9 7 6 9 7 10 2 9 8 7 0 Sugar beet 4 9 9 10 10 9 9 10 9 4 9 9 7 9 9 3 9 9 -- 10 7 9 Velvetleaf 2 9 5 7 7 9 9 8 7 3 5 7 8 7 7 8 8 3 0 2 3 6 Wheat 3 9 8 9 5 5 9 9 9 0 0 9 5 8 8 0 8 4 0 7 9 8 Wild buckwheat 9 7 6 9 9 10 -- 9 9 8 9 9 9 7 9 8 9 9 8 9 9 -- Wild oat 0 9 5 8 5 6 9 8 8 0 7 8 8 5 9 2 5 4 0 7 7 2 Barnyardgrass -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Rice Japonica -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Umbrella sedge -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- COMPOUND Rate (31 g/ha) 274 275 276 283 284 285 286 287 288 289 291 292 300 301 302 305 310 PREEMERGENCE Barley Igri 0 9 0 9 -- 0 10 2 2 5 4 0 3 1 5 8 0 Bedstraw 0 10 0 10 10 4 10 10 10 8 3 0 2 6 9 8 7 Blackgrass 8 10 4 10 10 9 10 10 9 9 8 0 8 9 10 10 8 Chickweed 0 10 0 10 10 10 10 10 10 9 8 2 4 9 10 9 7 Corn 0 10 0 9 9 4 6 4 4 2 4 0 3 1 3 3 4 Cotton 0 8 0 6 8 7 9 9 7 0 3 0 4 7 8 7 8 Crabgrass 0 9 0 6 8 2 9 9 8 0 7 0 4 4 7 7 0 Downy brome 0 10 0 10 10 3 10 10 9 7 8 0 5 8 10 8 0 Duck salad -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Giant foxtail 1 9 2 8 8 3 9 8 7 7 8 0 7 4 9 9 0 Lambsquarters 0 9 0 10 10 10 9 10 10 0 8 0 3 9 10 10 10 Morningglory 0 4 0 6 5 5 9 9 6 0 0 0 2 5 5 7 5 Pigweed 0 9 0 9 9 8 9 9 9 9 9 0 9 8 9 9 8 Rape 0 9 0 8 9 9 10 10 9 0 6 0 5 6 8 3 0 Ryegrass 0 9 0 10 8 3 10 9 5 3 7 0 2 0 8 3 0 Sorghum 2 10 5 9 9 2 9 9 8 6 6 0 5 4 8 9 0 Soybean 0 3 0 7 3 2 9 6 3 0 0 0 0 2 5 3 5 Speedwell 0 9 -- 10 10 4 10 2 10 10 9 4 7 10 10 10 10 Sugar beet 0 10 0 9 10 9 10 10 10 7 9 0 9 9 10 10 10 Velvetleaf 2 3 2 5 8 5 9 2 8 3 5 0 5 5 8 5 6 Wheat 0 9 0 9 -- 0 10 8 5 0 2 0 4 5 9 0 0 Wild buckwheat -- 10 0 9 10 10 9 9 9 8 3 2 4 7 9 9 9 Wild oat 0 8 0 9 2 2 9 4 1 2 4 0 2 3 3 0 0 Barnyardgrass -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Rice Japonica -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Umbrella sedge -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- COMPOUND Rate (16 g/ha) 1 2 3 5 7 11 13 14 25 26 27 28 29 30 31 34 35 36 50 51 53 58 59 60 63 64 71 77 78 POSTEMERGENCE Barley Igri 6 9 7 10 6 9 9 9 9 8 9 8 10 10 8 7 3 4 8 8 9 4 7 4 7 8 0 1 Bedstraw 9 8 9 10 0 5 8 4 10 10 10 10 10 10 7 5 10 10 8 10 8 10 10 10 7 7 7 4 6 Blackgrass 8 8 9 10 5 8 8 5 10 10 10 9 10 10 7 4 8 9 9 9 9 9 8 7 9 9 4 6 7 Chickweed 6 5 7 10 0 9 9 9 10 10 10 5 10 10 -- 10 10 10 8 10 9 7 10 10 10 10 9 3 5 Corn 7 8 10 10 6 10 10 10 10 10 10 10 10 10 9 10 10 10 7 10 6 10 9 7 10 10 5 4 7 Cotton 5 6 7 6 3 6 6 8 4 7 9 8 10 10 4 5 6 8 10 10 10 8 10 10 8 9 9 4 7 Crabgrass 7 5 6 7 4 5 7 6 6 5 7 4 10 10 4 6 3 6 3 6 6 3 0 0 3 7 5 4 3 Downy brome 8 7 6 10 6 8 5 4 10 9 10 10 10 10 5 7 7 9 6 8 9 4 7 4 8 7 0 3 0 Duck salad -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- 10 9 9 7 10 10 8 9 9 5 5 Giant foxtail 6 8 8 8 6 9 10 10 10 10 10 7 10 10 8 7 8 10 7 7 8 4 4 0 8 10 3 6 6 Lambsquarters 10 10 10 10 9 10 10 5 10 10 10 10 10 10 9 10 10 10 10 10 10 9 10 10 10 10 7 8 10 Morningglory 6 10 10 7 6 7 6 7 10 10 10 10 10 10 7 7 10 10 10 10 8 10 10 10 10 10 10 7 10 Pigweed 5 5 4 10 2 8 9 0 7 7 10 10 10 10 6 8 7 10 10 10 10 7 10 8 10 10 10 8 10 Rape 5 6 8 10 0 8 10 10 9 10 10 10 10 10 0 4 2 10 10 10 10 10 10 10 10 10 5 7 9 Ryegrass 9 5 3 10 3 9 4 3 10 10 10 10 10 10 7 9 7 10 7 9 9 2 9 4 7 9 2 3 2 Sorghum 7 8 10 10 7 8 10 8 10 10 10 10 10 10 8 7 10 10 7 10 6 6 6 6 10 10 5 7 8 Soybean 7 9 8 10 2 8 10 8 10 10 10 10 10 10 7 10 10 10 10 10 10 10 10 10 10 10 9 8 9 Speedwell 4 5 0 9 0 0 5 0 6 6 5 8 8 0 0 0 3 4 5 9 7 9 10 8 4 0 1 3 3 Sugar beet 9 10 10 10 5 9 9 8 8 9 10 10 10 10 8 9 10 10 9 10 10 9 10 10 10 10 7 10 10 Velvetleaf 6 7 6 8 3 6 8 3 7 9 10 9 9 10 5 6 7 6 10 10 10 10 8 6 10 10 8 6 8 Wheat 7 8 6 10 5 9 9 9 9 7 10 5 10 10 7 6 6 6 6 8 9 0 2 1 7 8 0 0 0 Wild buckwheat 10 6 9 10 0 9 5 3 10 6 10 10 10 10 6 0 0 4 7 10 8 6 10 10 6 8 0 4 7 Wild oat 9 10 8 9 5 8 4 3 9 9 9 6 9 9 8 7 8 9 5 9 7 2 7 4 5 6 0 0 0 Barnyardgrass 0 0 0 7 0 4 5 2 7 8 8 8 9 7 0 1 6 8 8 9 9 8 7 6 9 9 0 0 7 Rice Japonica 6 6 7 8 0 5 7 6 5 6 2 8 8 8 0 8 4 5 0 9 9 8 9 9 8 8 8 3 8 Umbrella sedge 6 9 9 8 0 7 0 1 9 9 9 9 8 7 0 2 0 4 9 9 9 8 9 9 8 9 0 5 9
TABLE B - COMPOUND Rate (16 g/ha) 81 82 83 84 86 88 89 102 103 107 108 109 110 111 112 114 1 15 116 117 118 119 120 121 122 POSTEMERGENCE Barley Igri 7 6 6 5 5 6 6 8 8 9 7 10 10 9 7 6 3 5 2 0 10 5 9 8 Bedstraw 5 8 9 8 9 9 10 8 9 10 10 -- 10 10 9 10 -- 10 10 9 9 9 10 10 Blackgrass 10 9 10 9 9 8 9 9 9 10 9 10 10 10 10 9 -- 9 8 7 10 10 9 9 Chickweed 7 10 10 9 -- 9 8 9 9 10 10 9 10 9 8 8 -- 10 10 3 10 10 10 10 Corn 0 5 9 8 0 4 8 2 0 10 10 7 9 10 8 9 9 5 3 0 10 10 10 10 Cotton 5 5 9 8 4 8 4 3 7 10 10 9 9 10 8 8 9 9 9 3 10 10 10 10 Crabgrass 2 4 5 3 2 0 0 0 0 5 2 6 7 0 0 0 0 0 0 0 -- 0 5 4 Downy brome 6 5 3 3 3 5 3 7 7 8 4 9 10 9 6 5 0 2 0 0 10 8 9 7 Duck salad 0 9 9 0 7 4 8 2 4 10 10 9 -- 7 9 4 3 6 5 4 8 7 9 8 Giant foxtail 6 8 8 7 5 4 2 5 4 9 3 7 8 7 2 7 4 5 0 0 -- 9 9 4 Lambsquarters 6 9 10 10 9 8 10 9 10 10 10 10 10 10 10 6 -- 7 -- 0 10 10 10 8 Morningglory 9 10 10 7 9 10 10 7 9 10 10 7 10 10 10 8 10 10 10 9 10 10 10 10 Pigweed 7 10 10 8 6 4 3 8 9 10 10 10 10 10 10 6 5 8 8 0 -- 10 10 10 Rape 9 10 8 9 10 9 10 9 8 10 10 10 10 10 10 9 9 9 9 9 10 10 10 10 Ryegrass 5 5 3 4 0 4 4 3 2 10 9 10 10 9 7 8 3 9 5 4 10 4 10 9 Sorghum 10 10 10 10 9 7 8 9 10 10 9 9 9 10 9 8 8 9 8 0 -- 10 10 9 Soybean 8 8 9 9 8 8 9 6 8 10 10 8 10 10 9 8 9 9 9 0 10 10 10 10 Speedwell -- -- -- 8 7 9 7 -- -- -- -- 6 9 5 9 9 -- 10 0 7 -- 0 10 0 Sugar beet 6 9 10 9 9 9 9 9 9 10 10 -- 10 10 9 6 -- 9 9 4 10 10 10 10 Velvetleaf 6 9 9 5 7 7 7 2 8 10 7 8 10 10 8 8 9 9 9 2 -- 10 10 8 Wheat 4 3 2 4 3 5 5 9 8 8 4 9 9 8 5 5 4 0 0 0 9 7 9 8 Wild buckwheat 9 7 8 9 8 8 9 8 7 9 10 9 9 8 9 8 -- 9 9 8 10 10 8 9 Wild oat 7 0 0 7 2 4 2 6 5 9 8 9 10 6 5 6 3 5 4 0 8 4 9 8 Barnyardgrass 4 8 8 3 8 8 8 1 2 8 8 9 9 8 7 8 9 7 4 5 8 5 8 8 Rice Japonica 6 8 8 5 8 3 6 2 2 9 8 8 8 8 8 8 7 7 7 5 7 6 8 8 Umbrella sedge 4 7 8 2 5 0 6 0 7 9 8 8 8 8 8 7 9 9 8 8 9 8 9 8 COMPOUND Rate (16 g/ha) 125 166 167 170 172 173 203 204 205 206 207 208 209 211 212 213 214 217 218 219 225 229 POSTEMERGENCE Barley Igri 0 8 9 5 9 9 8 10 10 9 9 9 0 9 8 5 6 9 7 6 9 8 Bedstraw 0 9 10 10 9 9 8 9 10 9 10 10 0 9 10 10 10 6 8 10 8 9 Blackgrass 4 9 9 9 10 10 9 10 10 10 10 10 5 10 8 8 7 8 7 7 6 9 Chickweed 4 10 10 10 6 6 8 10 10 10 9 8 0 8 6 10 10 6 9 10 9 8 Corn 3 10 10 10 8 9 10 10 10 10 10 9 0 9 10 10 9 10 9 7 10 9 Cotton 8 7 7 10 5 8 7 5 8 7 6 9 0 6 7 9 10 6 4 6 7 0 Crabgrass 0 5 3 10 6 9 9 10 10 10 10 9 0 5 5 4 3 6 3 0 7 3 Downy brome 0 7 9 6 9 9 10 10 10 10 10 9 0 9 9 7 7 8 7 6 9 7 Duck salad 1 8 7 9 2 3 8 9 10 9 9 10 0 10 8 9 9 0 0 0 0 0 Giant foxtail 0 7 7 10 8 9 6 9 10 10 10 10 5 8 8 6 5 7 5 0 8 7 Lambsquarters 8 10 10 10 9 9 10 10 10 10 10 10 0 10 10 10 10 10 10 10 10 8 Morningglory 10 8 9 9 9 9 10 10 10 7 7 10 0 10 10 10 10 10 10 7 9 9 Pigweed 8 8 5 10 9 9 10 10 10 10 9 10 0 10 5 10 10 7 7 8 10 8 Rape 9 10 10 10 0 7 10 10 10 10 9 10 0 8 9 10 10 9 7 8 10 6 Ryegrass 0 8 9 8 9 9 10 10 10 10 6 10 0 4 3 8 6 9 6 7 5 4 Sorghum 3 10 10 10 6 9 10 10 10 10 10 10 5 7 10 10 10 10 7 4 9 8 Soybean 8 9 8 10 9 9 8 10 10 10 10 7 0 10 9 10 10 7 9 7 10 8 Speedwell 0 8 4 9 9 6 5 8 3 8 0 5 0 8 0 10 7 3 0 3 5 2 Sugar beet 9 10 10 10 8 9 10 10 10 10 9 10 0 8 7 10 10 9 9 10 10 6 Velvetleaf 8 9 9 9 7 7 10 10 10 8 7 9 0 10 8 9 4 8 8 8 8 8 Wheat 0 8 8 9 9 9 7 9 9 9 8 8 0 8 7 6 3 9 5 5 6 7 Wild buckwheat -- 7 8 9 -- 9 9 9 10 9 7 9 0 7 9 10 10 7 8 8 8 6 Wild oat 0 8 9 5 9 9 8 10 9 9 9 6 0 6 6 6 6 9 5 5 5 8 Barnyardgrass 0 2 0 9 0 0 1 9 9 9 8 9 0 9 6 9 5 3 6 5 3 0 Rice Japonica 0 6 5 9 0 4 9 9 9 9 9 9 0 9 8 8 8 8 8 8 8 0 Umbrella sedge 9 10 9 7 5 7 9 9 9 9 9 9 0 9 9 9 9 8 8 8 7 0 COMPOUND Rate (16 g/ha) 230 231 232 240 241 242 243 244 245 252 254 256 258 259 261 266 267 268 269 270 271 272 POSTEMERGENCE Barley Igri 8 8 8 9 9 10 10 9 9 9 5 9 9 8 10 8 9 8 6 9 9 9 Bedstraw 9 9 9 10 10 10 10 10 10 10 9 10 9 8 10 9 10 10 8 10 10 10 Blackgrass 9 9 10 10 10 10 10 10 10 10 9 9 9 9 9 10 10 9 9 10 10 10 Chickweed 3 6 10 10 10 10 -- 10 4 4 10 8 10 8 9 3 9 9 0 6 10 10 Corn 9 10 9 10 10 10 10 10 10 10 8 10 10 10 10 10 10 10 6 10 10 10 Cotton 0 5 4 6 9 8 8 9 7 6 8 0 2 3 2 1 7 7 1 8 8 5 Crabgrass 0 7 6 6 8 10 10 9 8 2 0 8 9 3 6 0 0 0 0 9 9 9 Downy brome 5 9 9 9 10 10 10 10 9 10 7 9 9 9 9 8 10 8 6 8 10 9 Duck salad 2 0 0 6 7 8 8 5 9 0 3 2 3 0 0 0 1 2 0 0 0 0 Giant foxtail 6 6 5 8 10 10 10 10 9 8 2 9 10 9 10 7 4 5 0 8 9 10 Lambsquarters 10 9 10 10 9 10 10 7 9 0 0 10 10 10 9 4 7 0 0 10 10 9 Morningglory 9 8 7 10 10 10 10 10 10 10 9 10 10 7 10 10 9 10 5 8 9 9 Pigweed 9 10 4 10 10 10 10 10 10 5 8 9 10 10 9 2 10 9 5 10 9 10 Rape 7 9 6 10 10 10 10 10 10 9 9 10 10 8 10 7 9 9 8 9 9 9 Ryegrass 0 9 8 10 10 10 10 10 10 4 4 10 9 10 9 0 10 9 4 8 9 10 Sorghum 8 10 10 10 10 10 10 10 10 9 8 10 10 10 10 9 10 10 7 10 10 10 Soybean 8 9 9 9 10 9 9 9 9 8 9 7 10 8 8 10 9 10 3 5 7 6 Speedwell -- -- -- 4 4 -- 10 0 6 3 0 0 0 0 0 -- 8 0 0 -- 0 0 Sugar beet 3 9 8 10 9 10 10 10 10 7 9 8 9 9 8 2 10 10 0 9 9 9 Velvetleaf 6 8 6 6 8 10 10 9 8 4 3 9 9 5 3 7 8 4 0 6 7 8 Wheat 5 9 8 9 9 10 10 9 9 8 0 8 8 7 7 3 9 7 3 9 9 9 Wild buckwheat 9 9 9 10 10 10 9 -- 10 7 9 9 9 3 10 8 9 9 -- 10 10 10 Wild oat 8 8 8 10 10 10 10 9 9 7 6 9 9 8 8 7 9 7 4 9 9 9 Barnyardgrass 0 2 0 0 6 9 9 7 9 2 1 6 7 8 9 0 0 0 0 0 0 3 Rice Japonica 0 7 6 6 7 8 9 9 8 5 7 9 8 8 9 0 8 6 5 5 3 8 Umbrella sedge 0 2 0 7 8 9 8 8 9 8 7 8 9 3 9 2 4 2 0 9 8 9 COMPOUND Rate (31 g/ha) 274 275 276 283 284 285 286 287 288 289 291 292 300 301 302 305 310 POSTEMERGENCE Barley Igri 3 8 7 10 10 10 10 10 10 9 9 3 9 9 10 9 9 Bedstraw 0 10 5 10 10 10 10 10 10 10 10 7 9 10 10 10 10 Blackgrass 9 10 9 10 9 10 10 10 10 10 10 9 10 10 10 10 8 Chickweed 0 8 0 10 10 10 10 10 10 10 10 8 10 9 10 9 6 Corn 3 10 8 10 10 10 10 10 10 10 10 10 9 9 10 9 9 Cotton 0 5 0 10 10 10 10 10 7 8 7 5 5 7 8 5 6 Crabgrass 2 10 0 9 8 8 10 9 7 7 9 5 8 8 10 8 2 Downy brome 6 9 6 10 10 10 10 10 9 9 9 3 9 9 9 8 8 Duck salad 0 5 0 8 6 2 6 8 9 0 6 0 4 0 7 5 0 Giant foxtail 2 10 3 10 10 10 10 10 10 9 10 6 9 9 10 10 8 Lambsquarters 0 9 0 10 10 10 -- 10 10 8 9 5 10 10 10 9 8 Morningglory 0 7 6 8 10 10 10 10 10 8 8 1 6 8 9 8 10 Pigweed 2 9 5 10 10 10 10 10 8 7 9 7 7 9 9 8 6 Rape 0 9 0 10 10 10 10 10 10 0 9 9 9 9 9 9 9 Ryegrass 0 10 0 10 7 3 10 9 6 5 9 4 9 9 10 9 4 Sorghum 3 10 8 10 10 10 10 10 10 10 10 9 8 9 10 10 8 Soybean 0 6 0 9 9 9 10 10 10 8 8 0 8 9 10 8 9 Speedwell 0 3 0 7 7 0 10 0 10 4 0 8 9 10 5 10 9 Sugar beet 0 9 2 8 8 9 10 10 10 9 9 9 9 10 10 9 10 Velvetleaf 0 5 1 8 10 10 10 5 10 4 6 4 5 5 8 7 9 Wheat 6 9 4 9 9 9 10 9 9 9 9 2 9 9 9 9 4 Wild buckwheat 6 -- -- 10 10 10 10 10 10 -- 9 9 9 8 9 7 8 Wild oat 4 9 6 10 9 9 9 9 9 8 9 4 9 10 10 8 9 Barnyardgrass 0 7 0 8 3 0 9 9 9 0 2 0 4 6 9 9 0 Rice Japonica 0 8 1 8 3 3 9 9 8 0 3 2 6 5 4 7 0 Umbrella sedge 0 6 0 9 9 9 8 8 9 8 7 0 0 5 8 5 0 COMPOUND Rate (16 g/ha) 1 2 3 5 7 11 13 14 25 26 27 28 29 30 31 34 35 36 50 51 53 58 59 60 63 64 71 77 78 PREEMERGENCE Barley Igri 4 6 4 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 5 9 9 1 6 2 8 8 0 1 3 Bedstraw 7 9 10 10 0 5 8 7 8 8 8 8 9 10 2 6 9 10 9 10 10 8 10 9 9 9 9 0 8 Blackgrass 7 7 6 5 0 6 6 0 8 8 9 7 7 4 3 3 7 7 8 8 9 7 8 6 9 9 5 6 7 Chickweed 6 10 9 9 0 10 8 10 5 9 9 7 9 9 0 7 10 10 9 10 10 9 10 10 9 8 7 2 7 Corn 0 6 7 3 0 4 6 2 8 9 5 9 10 10 8 0 2 2 0 9 3 4 6 3 9 9 0 0 4 Cotton 0 3 5 7 0 3 6 2 5 7 7 5 9 8 0 0 7 8 7 10 8 3 9 9 8 9 6 0 6 Crabgrass 0 6 6 6 0 0 0 0 7 9 8 7 9 9 2 4 4 8 7 10 9 5 4 0 9 9 0 0 5 Downy brome 6 7 5 10 4 0 5 0 2 2 3 5 5 5 0 0 7 7 5 9 9 5 7 6 9 8 0 5 2 Duck salad -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Giant foxtail 2 7 6 3 0 5 0 0 6 8 8 7 8 9 6 4 2 8 7 8 9 4 0 0 9 9 0 3 5 Lambsquarters 9 9 9 10 -- 8 9 8 3 8 7 5 9 8 5 -- 10 10 10 10 10 8 10 10 10 10 8 2 6 Morningglory 0 0 5 7 0 1 2 0 6 6 2 5 9 9 0 0 3 8 9 9 5 0 10 10 8 9 8 0 8 Pigweed 6 9 7 8 4 3 5 5 7 8 8 8 9 9 7 8 7 9 10 10 10 9 9 9 9 9 9 8 8 Rape 6 8 8 10 0 3 8 6 5 2 5 7 7 8 2 0 3 7 9 9 9 10 10 10 10 10 9 8 9 Ryegrass 4 2 0 6 0 3 5 2 3 4 4 4 3 4 0 0 4 6 9 9 9 7 10 8 9 9 3 2 5 Sorghum 4 7 8 8 3 3 5 4 10 10 9 9 10 10 3 3 9 8 7 10 9 9 8 7 9 9 6 5 7 Soybean 3 4 3 6 0 0 0 0 3 3 4 2 9 8 0 2 0 5 6 8 6 3 7 7 8 8 7 2 6 Speedwell 6 9 -- 10 0 4 8 6 8 8 0 7 9 0 0 5 8 7 9 10 10 8 10 8 9 8 2 0 0 Sugar beet 6 8 7 10 0 8 8 7 5 9 8 8 9 10 2 6 10 10 9 9 9 9 10 10 10 10 9 2 9 Velvetleaf 3 7 -- 8 0 1 5 0 7 7 7 7 8 8 0 0 5 5 7 9 7 6 10 7 8 9 9 0 6 Wheat 5 6 4 7 0 0 0 0 2 2 0 0 2 1 0 0 0 0 5 9 9 0 5 3 7 8 0 0 1 Wild buckwheat 9 9 9 10 0 4 8 5 4 7 2 5 8 8 0 0 9 9 8 9 9 3 9 8 9 8 5 1 6 Wild oat 1 3 0 2 0 0 0 0 2 2 0 2 2 2 0 0 3 0 4 9 7 2 6 6 5 4 0 0 0 Barnyardgrass -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Rice Japonica -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Umbrella sedge -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- COMPOUND Rate (16 g/ha) 81 82 83 84 86 88 89 102 103 107 108 109 110 111 112 114 1 15 116 117 118 119 120 121 122 PREEMERGENCE Barley Igri 6 5 4 2 4 5 6 5 6 9 8 8 6 2 0 5 0 7 3 0 9 6 9 8 Bedstraw 6 9 9 0 9 9 9 8 9 10 10 9 10 9 10 9 9 9 9 7 9 -- 9 10 Blackgrass 9 9 9 8 9 9 9 8 9 9 9 10 10 9 9 9 9 9 7 5 10 10 10 9 Chickweed 6 9 10 2 8 9 9 5 9 9 9 9 9 8 9 8 8 9 9 7 10 10 10 10 Corn -- -- -- 9 3 3 7 2 0 10 9 5 8 2 3 9 4 8 4 3 9 7 10 9 Cotton -- -- -- 8 9 -- 4 2 8 10 10 9 9 5 8 2 2 9 9 3 7 6 10 9 Crabgrass -- -- -- 2 4 0 5 0 0 8 8 8 6 0 3 7 2 8 2 0 6 5 2 5 Downy brome 6 7 5 3 5 4 5 3 6 9 7 9 9 4 6 5 3 6 4 2 10 5 8 8 Duck salad -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Giant foxtail -- -- -- 2 7 5 5 4 5 9 7 8 9 4 3 8 4 8 2 0 8 6 2 2 Lambsquarters 9 9 9 -- 10 6 9 9 9 10 10 9 10 9 9 9 8 9 8 9 10 10 10 9 Morningglory -- -- -- 5 8 5 6 7 7 10 10 6 7 6 8 8 7 9 10 5 8 8 9 9 Pigweed -- -- -- 3 8 8 8 8 9 9 10 9 10 9 9 9 9 9 8 6 9 8 9 9 Rape 9 9 9 3 9 9 9 9 9 9 10 9 9 7 9 9 8 9 9 4 10 10 10 10 Ryegrass 4 4 5 4 5 5 6 0 0 10 9 9 9 4 7 8 3 8 5 4 8 5 9 9 Sorghum -- -- -- 9 9 9 8 8 9 9 10 9 9 4 5 9 7 9 9 0 9 4 9 9 Soybean -- -- -- 7 5 7 6 0 2 10 8 8 6 4 3 3 0 8 6 0 8 5 10 7 Speedwell 9 9 9 7 9 9 9 9 8 10 7 9 10 8 9 9 8 10 7 9 10 9 10 4 Sugar beet 9 9 9 3 9 9 9 9 9 10 10 9 9 9 9 9 7 9 9 4 10 10 10 10 Velvetleaf -- -- -- 4 7 4 5 5 8 10 9 9 7 7 3 7 7 9 8 0 8 7 8 8 Wheat 5 4 3 3 3 2 3 2 5 8 0 8 7 3 2 0 0 0 0 0 8 6 9 8 Wild buckwheat 9 9 8 0 8 9 8 8 9 9 9 -- 7 -- 9 9 9 9 9 9 10 10 9 10 Wild oat 5 4 2 3 2 0 0 2 3 7 7 7 8 0 0 4 0 7 4 0 6 3 9 8 Barnyardgrass -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Rice Japonica -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Umbrella sedge -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- --
TABLE B - COMPOUND Rate (16 g/ha) 125 166 167 170 172 173 203 204 205 206 207 208 209 211 212 213 214 217 218 219 225 229 PREEMERGENCE Barley Igri 0 2 0 0 0 0 5 8 8 5 6 8 0 3 0 4 4 5 4 0 2 8 Bedstraw 5 9 7 9 3 0 5 8 10 9 9 9 0 9 2 10 10 2 6 8 7 3 Blackgrass 5 8 8 7 7 9 7 9 9 9 8 8 0 8 7 8 7 8 7 5 5 5 Chickweed 8 9 9 9 2 2 7 9 9 8 9 9 0 9 10 10 9 3 10 9 7 2 Corn 0 6 4 10 2 3 3 7 10 10 9 8 0 6 5 10 10 3 3 0 3 1 Cotton 0 5 0 9 4 -- 6 4 8 8 8 7 0 4 4 10 10 5 -- 2 9 0 Crabgrass 0 8 4 8 5 5 7 8 10 8 8 8 0 8 5 7 4 3 3 0 0 2 Downy brome 0 5 4 6 4 0 8 9 9 9 8 9 0 8 3 8 7 9 6 5 4 5 Duck salad -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Giant foxtail 0 7 2 8 7 7 0 9 9 8 9 9 0 8 4 7 2 3 4 0 2 4 Lambsquarters 9 8 9 9 9 9 8 9 10 10 9 9 0 9 -- 10 9 7 -- 8 8 -- Morningglory 2 5 2 8 3 2 4 7 9 8 8 8 0 0 4 10 9 2 3 0 7 0 Pigweed 8 8 6 9 9 8 8 10 10 10 9 10 0 9 6 10 9 7 8 6 6 9 Rape 8 9 -- 9 2 0 10 9 9 6 8 10 0 8 1 10 10 6 3 5 4 0 Ryegrass 0 6 3 6 2 5 7 8 9 9 8 9 0 3 0 7 5 5 2 2 0 0 Sorghum 0 9 9 9 4 4 7 9 9 10 10 10 0 10 5 10 8 9 5 0 9 7 Soybean 0 5 0 8 2 3 4 6 7 7 6 6 0 5 3 9 8 2 4 2 7 1 Speedwell 8 10 2 10 9 9 4 7 7 9 3 9 0 9 9 10 5 9 -- 0 9 7 Sugar beet 9 10 9 10 6 6 8 10 9 9 9 9 2 9 -- 10 9 8 7 8 8 0 Velvetleaf 3 6 4 9 4 4 7 7 8 9 8 8 0 7 2 10 7 5 4 0 8 5 Wheat 0 3 0 6 2 0 5 8 6 9 8 9 0 5 0 7 2 5 6 0 0 5 Wild buckwheat 8 5 7 8 9 9 9 9 9 8 7 8 3 8 4 9 9 2 0 8 8 4 Wild oat 0 2 0 0 0 0 5 6 7 4 5 5 0 2 0 5 4 3 2 0 0 0 Barnyardgrass -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Rice Japonica -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Umbrella sedge -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- COMPOUND Rate (16 g/ha) 230 231 232 240 241 242 243 244 245 252 254 256 258 259 261 266 267 268 269 270 271 272 PREEMERGENCE Barley Igri 0 8 4 7 7 4 7 5 9 0 4 8 4 2 9 0 8 4 0 6 8 1 Bedstraw 0 8 7 9 9 10 10 10 10 6 9 9 9 0 9 7 9 9 0 5 8 8 Blackgrass 6 8 7 10 10 10 10 10 10 9 8 10 10 9 9 9 9 9 8 9 10 10 Chickweed 5 0 0 9 10 9 9 10 8 9 9 0 9 0 9 4 6 3 0 0 8 10 Corn 0 0 5 9 9 9 10 10 9 6 4 8 5 8 9 0 5 3 0 4 3 0 Cotton 0 8 4 3 3 5 10 9 6 0 9 3 5 5 4 0 7 8 0 8 2 5 Crabgrass 2 4 4 8 9 9 7 9 8 0 0 6 4 7 5 2 5 4 0 7 7 8 Downy brome 0 9 10 9 10 9 10 9 9 6 8 9 8 9 9 4 10 9 0 8 10 9 Duck salad -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Giant foxtail 1 3 3 6 9 9 7 9 7 0 0 6 8 5 6 0 5 -- 0 5 7 9 Lambsquarters 4 4 2 10 10 9 9 9 10 7 7 8 10 9 9 9 9 8 2 7 8 7 Morningglory 0 8 7 6 5 6 9 8 8 0 9 3 4 2 8 2 7 7 0 0 6 0 Pigweed 5 8 8 8 9 10 10 10 9 5 8 5 8 8 8 2 7 7 0 9 9 10 Rape 0 0 0 9 9 7 10 9 9 6 9 9 7 3 9 3 6 5 0 0 0 7 Ryegrass 0 3 2 7 9 9 10 8 10 0 6 9 9 8 6 0 6 0 0 4 3 5 Sorghum 2 9 9 9 9 9 10 10 9 3 8 9 7 8 9 5 9 8 0 2 3 2 Soybean 0 8 7 5 6 7 9 8 5 2 8 4 5 4 2 2 5 6 0 0 0 0 Speedwell 5 0 0 9 10 4 10 0 10 10 8 8 0 4 9 6 10 0 9 8 4 0 Sugar beet 4 4 3 9 9 9 9 9 9 4 9 9 7 8 8 1 8 8 -- 9 5 9 Velvetleaf 0 8 2 6 7 6 9 8 7 0 2 6 8 5 3 6 5 3 0 2 3 3 Wheat 3 9 5 8 5 3 9 4 9 0 0 8 4 7 7 0 3 0 0 6 8 6 Wild buckwheat 4 0 -- 9 9 8 9 9 8 3 9 9 9 7 9 7 8 8 3 8 9 -- Wild oat 0 3 2 -- 4 3 9 3 8 0 3 8 4 2 6 0 5 0 0 7 6 0 Barnyardgrass -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Rice Japonica -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Umbrella sedge -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- COMPOUND Rate (16 g/ha) 274 275 276 283 284 285 286 287 288 289 291 292 300 301 302 305 310 PREEMERGENCE Barley Igri 0 9 0 9 9 0 9 0 0 2 3 0 0 0 0 3 0 Bedstraw 0 10 0 10 8 -- 10 10 10 6 2 0 0 5 7 7 4 Blackgrass 6 10 0 10 10 9 10 9 9 9 7 0 7 7 9 9 0 Chickweed 0 10 0 10 10 10 10 10 10 8 8 2 3 9 10 6 4 Corn 0 5 0 4 4 2 6 0 3 2 2 0 2 0 2 3 2 Cotton 0 7 0 5 5 6 9 8 7 0 3 0 2 3 8 5 8 Crabgrass 0 8 0 6 6 0 8 7 7 0 5 0 0 0 7 3 0 Downy brome 0 9 0 10 9 0 10 10 9 5 4 0 3 3 7 3 0 Duck salad -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Giant foxtail 0 9 0 6 6 1 9 4 6 2 8 0 2 2 9 5 0 Lambsquarters 0 6 0 9 10 9 9 10 10 0 8 0 2 9 10 8 0 Morningglory 0 2 0 5 5 2 9 5 5 0 0 0 0 3 3 6 2 Pigweed 0 9 0 9 9 8 9 9 9 8 9 0 7 7 9 8 3 Rape 0 9 0 -- 9 6 10 10 9 0 5 0 4 4 4 0 0 Ryegrass 0 6 0 10 2 0 9 4 5 0 4 0 0 0 4 0 0 Sorghum 0 10 2 9 6 0 9 5 4 2 4 0 2 2 5 8 0 Soybean 0 2 0 2 0 1 9 2 3 0 0 0 0 0 4 0 2 Speedwell 0 7 5 10 10 2 10 0 10 9 7 -- 5 10 10 10 9 Sugar beet 0 9 0 9 8 9 10 10 10 7 9 0 6 9 10 9 -- Velvetleaf 0 2 0 5 7 5 9 0 7 0 2 0 3 3 6 5 6 Wheat 0 9 0 9 9 0 9 3 4 0 2 0 2 4 2 0 0 Wild buckwheat -- 10 -- 9 9 9 9 9 9 7 3 0 3 6 9 8 9 Wild oat 0 4 0 7 0 0 0 2 0 2 3 0 0 0 0 0 0 Barnyardgrass -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Rice Japonica -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Umbrella sedge -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- COMPOUND Rate (8 g/ha) 1 2 3 5 7 11 13 14 25 26 27 28 29 30 31 34 35 36 50 51 53 5 8 59 60 63 64 71 77 78 POSTEMERGENCE Barley Igri 5 6 5 8 5 9 8 7 7 8 9 8 10 9 7 5 2 3 7 7 8 2 5 2 7 6 0 0 0 Bedstraw 8 8 -- 10 0 3 3 3 9 10 10 10 10 10 5 3 7 10 8 9 7 9 10 10 6 7 5 2 5 Blackgrass 5 8 7 9 5 7 6 3 8 10 10 9 9 10 6 3 7 5 9 8 8 8 7 6 9 9 2 5 6 Chickweed 5 5 6 9 0 9 8 8 9 10 10 3 10 10 -- 8 3 9 8 10 8 4 10 10 6 9 9 1 3 Corn 6 8 10 10 6 9 10 9 9 10 10 10 10 10 8 10 10 10 6 9 6 8 9 4 7 10 3 3 7 Cotton 4 4 6 6 2 5 4 6 3 4 7 6 9 9 3 0 4 7 9 10 10 7 9 10 6 8 8 3 6 Crabgrass 6 5 5 7 3 4 6 6 5 4 6 3 7 8 4 6 3 5 3 5 5 0 0 0 3 6 3 3 0 Downy brome 6 5 4 10 5 6 2 2 10 8 9 7 10 10 2 5 3 7 6 7 9 2 6 2 8 7 0 1 Duck salad -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- 9 9 9 7 10 10 8 8 9 0 4 Giant foxtail 6 6 8 7 6 8 6 9 10 10 10 6 10 10 7 7 7 8 6 6 8 3 3 0 7 9 0 5 6 Lambsquarters 9 10 10 10 8 9 8 5 10 10 10 9 10 10 9 5 10 10 10 10 10 7 10 10 10 10 5 8 8 Morningglory 6 10 7 6 6 6 4 6 10 10 10 10 10 10 6 7 9 10 10 10 8 10 8 9 9 10 9 7 8 Pigweed 3 4 3 10 0 7 8 0 7 6 10 8 10 9 6 7 7 8 9 10 8 3 10 8 10 10 10 7 9 Rape 2 5 7 10 0 6 10 10 3 6 9 9 10 10 0 3 0 9 10 10 10 9 10 10 10 10 5 7 8 Ryegrass 6 3 0 9 4 5 3 2 10 10 9 8 10 9 0 5 4 7 5 9 8 0 9 4 7 8 0 2 2 Sorghum 6 7 8 10 7 7 10 7 10 10 10 10 10 10 8 7 8 10 7 9 6 6 4 4 10 10 4 7 7 Soybean 6 7 7 10 0 7 10 8 8 10 10 10 10 10 6 7 10 10 10 10 10 10 10 10 9 10 9 7 8 Speedwell 4 4 0 8 0 0 2 0 5 2 0 5 8 0 0 0 0 0 4 9 7 9 10 6 -- -- 0 2 2 Sugar beet 9 10 9 10 3 9 9 6 6 8 10 9 10 10 6 8 9 10 9 10 9 7 10 10 10 10 3 9 8 Velvetleaf 5 5 5 7 0 4 6 0 6 8 8 8 7 10 4 5 6 6 10 10 10 10 7 5 9 10 7 3 7 Wheat 5 4 0 9 4 9 8 8 8 4 9 5 10 9 4 4 4 4 5 8 9 0 0 0 7 7 0 0 0 Wild buckwheat 9 6 6 -- 0 8 2 3 8 6 9 9 10 10 0 0 0 3 6 10 7 5 10 10 6 7 0 2 5 Wild oat 8 7 7 7 4 8 2 2 8 8 8 6 7 9 6 5 7 8 4 8 6 2 5 3 5 5 0 0 0 Barnyardgrass 0 0 0 5 0 3 3 0 3 7 4 8 6 5 0 0 0 7 5 9 9 7 7 5 8 8 0 0 5 Rice Japonica 3 2 0 8 0 0 4 4 3 3 0 8 8 8 0 6 0 5 0 9 9 7 8 9 7 8 8 0 6 Umbrella sedge 5 8 9 6 0 3 0 0 9 8 9 7 2 4 0 2 0 0 9 9 9 8 9 9 8 9 0 4 9 COMPOUND Rate (8 g/ha) 81 82 83 84 86 88 89 102 103 107 108 109 110 111 112 114 115 116 117 118 119 120 121 122 POSTEMERGENCE Barley Igri 2 4 5 4 5 3 5 8 8 8 6 10 10 8 6 6 3 4 0 0 9 5 7 5 Bedstraw 5 7 9 7 6 8 10 8 8 10 10 8 9 9 9 9 10 10 10 9 8 9 10 10 Blackgrass 9 9 9 9 8 8 9 9 8 10 8 10 10 10 10 9 9 8 7 6 10 10 9 9 Chickweed 5 10 9 7 2 8 5 5 8 10 10 9 9 6 8 7 5 10 10 0 9 10 10 10 Corn 0 4 6 6 0 1 7 0 0 10 10 4 9 9 8 9 9 4 0 0 10 10 10 10 Cotton 5 -- 9 8 4 7 4 2 7 10 10 8 8 10 8 7 8 9 9 3 9 10 10 8 Crabgrass 2 2 5 2 0 0 0 0 0 5 0 4 4 0 0 0 0 0 0 0 0 0 3 3 Downy brome 3 2 2 0 3 5 0 7 6 8 3 9 9 8 5 4 0 2 0 0 9 7 8 6 Duck salad 0 6 7 0 7 0 7 0 0 10 9 9 9 0 6 4 0 6 5 2 8 6 8 7 Giant foxtail 5 6 7 4 4 2 0 4 2 6 2 6 7 4 0 6 3 4 0 0 7 6 7 2 Lambsquarters 5 8 10 9 9 8 9 9 9 10 10 10 10 10 10 5 5 5 0 0 10 10 10 4 Morningglory 8 10 10 7 8 9 10 7 8 10 10 5 10 10 10 7 9 10 10 8 10 10 10 10 Pigweed 7 8 10 8 4 2 2 7 9 10 8 8 8 10 10 6 3 7 5 0 10 10 10 10 Rape 8 9 7 9 9 9 10 9 7 10 9 10 10 10 10 9 9 9 9 9 10 10 10 10 Ryegrass 0 4 0 0 0 3 0 3 2 10 7 10 10 7 6 7 3 9 5 4 9 3 9 8 Sorghum 10 9 10 9 9 7 8 9 9 10 9 9 8 10 9 7 8 9 7 0 9 10 9 8 Soybean 7 8 9 8 6 8 9 5 8 10 10 8 10 10 8 8 8 8 9 0 10 10 10 10 Speedwell 2 4 0 -- -- 8 4 -- -- -- -- 6 8 4 9 9 2 10 0 4 9 0 10 Sugar beet 6 9 10 9 8 9 9 9 9 10 10 9 10 10 8 6 5 9 9 3 10 10 10 10 Velvetleaf 5 9 9 4 6 2 6 1 7 10 6 8 9 10 8 8 9 9 6 0 10 10 10 6 Wheat 0 3 2 2 2 4 3 8 6 8 3 9 9 6 5 4 4 0 0 0 9 5 9 5 Wild buckwheat 9 7 8 4 5 8 8 5 5 9 10 8 9 -- 7 7 8 9 9 8 10 10 8 9 Wild oat 4 0 0 5 0 2 0 5 5 9 7 9 9 6 5 5 0 4 3 0 8 4 9 8 Barnyardgrass 2 8 8 3 8 0 2 0 2 8 7 8 8 6 6 8 8 6 3 3 6 3 8 2 Rice Japonica 0 6 7 3 6 0 2 0 0 9 8 8 8 7 8 8 7 7 6 4 6 3 8 7 Umbrella sedge 0 7 8 0 3 0 4 0 3 9 8 8 8 8 7 7 9 9 8 7 9 8 8 8 COMPOUND Rate (8 g/ha) 125 166 167 170 172 173 203 204 205 206 207 208 209 211 212 213 214 217 218 219 225 229 POSTEMERGENCE Barley Igri 0 6 9 4 9 9 7 9 10 9 7 7 0 9 7 4 4 8 5 3 8 7 Bedstraw 0 9 9 9 6 9 7 9 10 9 8 10 0 8 9 10 10 5 7 9 7 9 Blackgrass 0 8 8 9 10 10 9 10 10 10 10 9 2 9 8 7 7 7 6 6 5 9 Chickweed 0 10 9 10 5 4 7 9 10 10 7 7 0 8 5 10 10 3 8 8 8 7 Corn 0 10 10 10 8 8 10 10 10 10 10 9 0 8 10 9 8 8 7 7 9 8 Cotton 7 5 7 9 5 5 6 4 8 4 6 7 0 4 6 8 10 6 4 4 6 0 Crabgrass 0 5 3 10 5 8 8 10 10 10 9 8 0 3 4 3 2 5 2 0 6 2 Downy brome 0 7 9 4 8 9 9 9 10 10 10 5 0 9 6 7 6 7 7 4 6 5 Duck salad 0 8 6 8 0 0 7 9 9 9 9 9 0 9 8 7 8 0 0 0 0 0 Giant foxtail 0 5 4 10 8 9 5 8 10 10 10 10 0 8 7 5 3 6 5 0 6 6 Lambsquarters 7 10 10 10 9 9 10 10 10 10 9 10 0 10 10 10 10 10 10 10 10 8 Morningglory 10 8 7 9 9 8 9 10 10 7 7 10 0 8 10 10 10 10 9 4 8 8 Pigweed 8 4 5 10 8 9 10 10 10 10 5 10 0 8 3 9 9 5 6 7 8 7 Rape 9 9 9 10 0 6 9 10 10 9 9 10 0 6 8 10 10 9 7 7 9 3 Ryegrass 0 8 8 8 6 9 8 10 10 10 6 7 0 3 2 8 6 5 4 6 3 0 Sorghum 2 9 10 10 6 8 10 10 10 10 10 10 3 7 10 10 10 8 6 3 8 8 Soybean 5 8 8 8 8 9 7 10 10 10 8 6 0 9 6 10 10 6 8 7 7 8 Speedwell 0 7 0 9 9 2 5 4 3 8 0 3 0 7 0 10 7 2 0 3 3 -- Sugar beet 7 10 10 10 8 9 10 10 10 10 8 10 0 8 7 10 10 8 9 9 9 2 Velvetleaf 8 8 7 9 6 5 7 8 10 7 5 7 0 8 8 8 3 5 5 7 6 7 Wheat 0 8 8 8 9 9 5 8 9 7 7 6 0 7 4 5 0 8 4 3 3 5 Wild buckwheat -- 6 6 9 9 8 8 9 9 9 7 7 0 7 8 10 9 3 7 7 6 5 Wild oat 0 8 8 5 6 8 7 9 9 9 8 5 0 5 4 5 4 8 4 4 4 6 Barnyardgrass 0 0 0 8 0 0 1 5 8 9 7 9 0 9 6 8 3 0 1 3 0 0 Rice Japonica 0 4 0 8 0 0 9 6 9 8 9 9 0 8 8 8 8 7 7 6 5 0 Umbrella sedge 9 9 9 6 2 4 7 9 9 9 9 9 0 9 8 9 9 2 4 3 0 0 COMPOUND Rate (8 g/ha) 230 231 232 240 241 242 243 244 245 252 254 256 258 259 261 266 267 268 269 270 271 272 POSTEMERGENCE Barley Igri 6 6 7 9 9 10 9 7 9 6 5 8 9 7 9 6 9 6 5 9 9 9 Bedstraw 6 9 9 9 10 10 10 10 10 10 9 9 9 5 9 9 10 9 6 9 10 9 Blackgrass 9 9 9 10 10 10 10 10 10 9 8 9 9 9 9 9 10 9 9 10 10 10 Chickweed 3 4 10 10 10 10 10 10 0 3 9 8 9 3 7 0 7 9 0 5 10 10 Corn 8 8 8 10 10 10 10 10 10 9 7 10 10 9 10 9 9 10 6 10 10 10 Cotton 0 5 4 4 8 8 8 8 7 3 8 0 0 0 0 0 7 6 0 7 7 5 Crabgrass 0 5 4 6 8 8 9 8 8 2 0 7 8 0 4 0 0 0 0 8 7 7 Downy brome 5 8 8 9 9 10 10 10 8 9 6 9 9 9 9 7 9 8 5 -- 10 9 Duck salad 2 0 0 5 6 8 7 4 7 0 2 0 0 0 0 0 0 0 0 0 0 0 Giant foxtail 5 5 3 8 10 9 9 10 8 6 0 9 10 9 10 6 3 2 0 6 9 10 Lambsquarters 9 9 10 9 9 10 10 5 8 -- 0 9 10 10 8 -- -- 0 0 10 10 9 Morningglory 9 8 7 9 10 10 10 10 10 8 9 9 10 6 10 10 8 9 4 8 8 8 Pigweed 8 10 4 10 9 10 10 10 10 5 8 8 9 9 9 2 9 8 5 10 9 8 Rape 6 9 5 9 10 10 10 10 10 9 9 9 10 8 10 6 9 9 6 8 9 9 Ryegrass 0 9 6 10 9 10 10 9 9 0 4 9 9 9 9 0 8 7 0 5 9 10 Sorghum 8 9 10 9 10 10 10 10 10 9 8 10 10 10 10 9 10 9 6 10 10 10 Soybean 8 9 9 8 10 9 9 9 9 8 9 5 9 7 7 8 9 9 0 5 7 6 Speedwell 0 -- -- 3 3 -- 10 0 4 2 0 0 0 0 0 0 7 0 0 2 0 -- Sugar beet 2 9 7 9 9 10 10 10 9 5 9 6 9 9 7 0 9 9 0 9 9 9 Velvetleaf 6 8 5 5 7 9 8 8 8 4 0 7 8 3 2 2 7 3 0 4 4 3 Wheat 4 9 8 9 9 10 10 6 8 5 0 7 7 7 7 3 8 4 3 9 9 9 Wild buckwheat 6 8 8 10 10 10 9 8 9 -- 9 9 9 0 10 7 9 9 6 10 10 10 Wild oat 7 8 7 9 9 10 10 9 9 4 6 8 9 8 7 5 8 7 4 9 9 9 Barnyardgrass 0 0 0 0 2 6 8 0 8 0 0 0 4 5 8 0 0 0 0 0 0 0 Rice Japonica 0 2 0 3 0 7 8 5 8 4 6 8 0 7 8 0 6 0 2 3 2 8 Umbrella sedge 0 0 0 7 8 8 7 8 8 6 3 8 9 0 8 0 2 0 0 8 4 8
TABLE B - COMPOUND Rate (8 g/ha) 274 275 276 283 284 285 286 287 288 289 291 292 300 301 302 305 310 POSTEMERGENCE Barley Igri 0 8 6 9 10 9 10 10 9 8 9 2 9 9 10 9 7 Bedstraw 0 6 2 10 10 10 10 10 10 9 9 6 9 10 10 10 9 Blackgrass 8 10 8 10 9 9 10 9 10 10 10 9 9 10 9 10 7 Chickweed 0 6 0 10 10 10 10 10 10 9 9 8 9 9 10 9 5 Corn 0 10 8 10 10 10 10 10 10 10 9 9 8 9 10 9 8 Cotton 0 4 0 10 8 10 9 9 6 7 7 4 4 4 7 2 4 Crabgrass 0 8 0 8 5 6 9 8 4 7 8 4 6 6 9 7 2 Downy brome 4 9 5 10 9 10 10 10 9 9 9 2 9 9 9 8 5 Duck salad 0 2 0 8 5 0 3 3 9 0 2 0 3 0 3 2 0 Giant foxtail 0 10 0 10 9 10 10 10 9 9 10 4 9 8 9 9 6 Lambsquarters 0 9 0 9 10 10 10 9 10 8 9 5 10 10 10 9 7 Morningglory 0 6 5 6 10 10 10 10 10 7 8 0 3 7 9 7 9 Pigweed 0 8 5 10 8 8 10 10 8 7 9 7 5 8 8 7 5 Rape 0 9 0 10 10 10 10 10 10 0 9 9 9 9 9 9 9 Ryegrass 0 9 0 9 4 0 10 8 5 4 9 3 8 7 9 5 0 Sorghum 0 10 8 10 10 10 10 10 10 9 10 9 7 9 10 10 8 Soybean 0 5 0 9 9 9 10 10 10 8 8 0 8 8 10 8 8 Speedwell 0 0 0 5 6 0 10 0 9 4 0 5 8 10 0 9 9 Sugar beet 0 9 0 8 -- 9 10 10 10 9 8 9 9 9 10 9 10 Velvetleaf 0 1 0 7 10 10 9 1 9 2 6 2 2 2 6 4 8 Wheat 5 9 4 9 9 9 10 5 8 7 9 0 8 8 9 8 3 Wild buckwheat -- 10 0 10 -- 10 10 10 10 -- 9 7 8 8 6 -- 8 Wild oat 3 9 4 10 9 5 9 9 9 6 9 4 9 9 9 7 5 Barnyardgrass 0 0 0 6 0 0 6 7 8 0 0 0 4 3 7 6 0 Rice Japonica 0 8 0 7 3 2 3 7 8 0 2 0 0 3 3 6 0 Umbrella sedge 0 4 0 9 8 6 0 0 9 6 3 0 0 2 6 2 0 COMPOUND Rate (8 g/ha) 1 2 3 5 7 11 13 14 25 26 27 28 29 30 31 34 35 36 50 51 53 5 8 59 60 63 64 71 77 78 PREEMERGENCE Barley Igri 2 5 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 4 6 6 0 6 0 7 7 0 0 0 Bedstraw -- 4 6 10 0 5 7 5 5 6 3 5 5 8 2 3 3 8 8 10 9 7 10 9 7 9 8 0 7 Blackgrass 5 6 6 3 0 4 3 0 7 7 7 5 5 4 2 0 5 6 7 8 9 7 7 6 9 9 5 3 5 Chickweed 4 8 9 7 0 8 8 10 2 8 4 5 9 8 0 4 8 10 9 10 10 9 10 10 7 8 7 0 5 Corn 0 4 3 0 0 4 0 0 4 4 4 4 6 8 2 0 0 2 0 7 0 0 5 2 4 9 0 0 3 Cotton 0 2 2 7 0 2 5 2 4 6 7 5 8 8 0 0 4 7 6 9 7 0 9 9 6 8 5 0 4 Crabgrass 0 5 5 5 0 0 0 0 4 8 7 6 7 8 0 2 2 5 6 9 9 4 3 0 8 8 0 0 4 Downy brome 5 6 0 6 0 0 3 0 0 0 0 4 3 4 0 0 4 4 5 8 9 3 6 5 9 8 0 2 0 Duck salad -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Giant foxtail 0 5 3 3 0 2 0 0 2 7 4 3 7 9 4 2 0 6 6 7 8 3 0 0 9 9 0 0 3 Lambsquarters 8 8 8 10 0 6 8 7 0 7 2 5 5 8 5 6 10 10 9 10 9 7 10 10 9 10 7 2 5 Morningglory 0 0 3 6 0 0 0 0 5 6 2 4 5 7 0 0 3 5 9 9 5 0 9 9 6 9 7 0 7 Pigweed 4 7 6 6 0 3 4 2 7 8 8 8 8 9 2 7 6 8 10 10 9 7 9 9 9 9 9 8 8 Rape 4 4 6 5 0 0 7 6 4 2 3 5 4 8 0 0 0 5 7 9 9 9 10 10 10 9 8 5 8 Ryegrass 0 0 0 0 0 0 3 0 0 2 2 4 0 3 0 0 3 3 7 9 9 3 10 7 6 8 0 0 1 Sorghum 3 4 4 8 0 0 2 3 7 9 5 9 10 9 2 0 4 5 6 9 8 5 7 6 9 9 4 4 6 Soybean 0 3 2 5 0 0 0 0 3 3 3 2 6 4 0 0 0 4 5 7 5 2 6 6 7 7 6 0 4 Speedwell -- 7 5 10 0 4 7 6 7 8 0 7 9 0 0 3 7 6 9 10 10 3 10 8 7 7 0 0 0 Sugar beet 5 8 7 10 0 4 8 6 3 8 3 5 5 9 0 5 8 9 9 9 9 8 10 10 10 10 9 0 9 Velvetleaf 0 4 3 6 0 0 4 0 7 6 4 5 8 3 0 0 3 5 6 9 7 5 9 6 8 9 8 0 6 Wheat 2 5 3 5 0 0 0 0 2 0 0 0 0 0 0 0 0 0 5 6 6 0 4 0 6 6 0 0 0 Wild buckwheat 6 9 9 10 0 2 7 3 2 2 0 5 5 7 0 0 7 7 8 9 9 3 8 8 8 7 5 0 6 Wild oat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 8 6 0 6 4 0 3 0 0 0 Barnyardgrass -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Rice Japonica -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Umbrella sedge -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- COMPOUND Rate (8 g/ha) 81 82 83 84 86 88 89 102 103 107 108 109 110 111 112 114 115 116 117 118 119 120 121 122 PREEMERGENCE Barley Igri 4 3 0 0 3 3 5 5 4 8 4 8 6 0 0 2 0 5 2 0 9 3 7 0 Bedstraw 5 9 9 0 8 4 9 7 9 10 10 9 10 3 9 9 8 9 9 0 4 2 8 8 Blackgrass 8 9 9 7 9 9 9 6 8 9 9 10 9 9 8 8 8 8 7 5 10 10 9 6 Chickweed 3 9 9 0 5 7 9 3 6 9 9 9 9 8 8 8 7 9 8 6 10 9 10 9 Corn -- -- -- 8 2 1 4 0 0 10 9 5 7 2 2 8 4 7 4 3 8 5 10 7 Cotton -- -- -- 8 -- 5 2 0 8 10 10 6 8 5 5 -- 0 9 8 0 7 6 9 8 Crabgrass -- -- -- 2 4 0 4 0 0 8 7 7 4 0 0 5 2 7 0 0 5 5 0 5 Downy brome 5 5 4 2 0 3 5 2 5 8 5 8 9 0 3 5 2 5 3 0 9 5 8 5 Duck salad -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Giant foxtail -- -- -- 2 4 2 5 3 2 8 6 7 8 3 0 8 3 6 0 0 6 5 0 0 Lambsquarters 9 9 9 5 -- -- 9 5 9 10 9 9 10 9 9 8 6 9 8 8 10 10 10 9 Morningglory -- -- -- 4 5 3 6 4 7 10 9 6 5 5 5 7 7 9 9 3 8 8 9 8 Pigweed -- -- -- 2 7 7 8 8 9 9 9 9 9 8 8 9 9 9 8 6 9 8 8 8 Rape 9 9 8 0 9 8 9 7 7 9 9 9 9 6 9 9 7 9 9 4 10 9 10 10 Ryegrass 4 4 3 3 4 4 5 0 0 10 9 9 9 3 4 8 0 8 5 0 8 4 8 0 Sorghum -- -- -- 9 9 5 8 7 9 9 9 7 9 4 5 8 4 9 9 0 8 4 9 8 Soybean -- -- -- 6 5 5 4 0 0 10 8 6 5 3 1 2 0 8 5 0 8 5 8 6 Speedwell 7 9 9 6 9 9 8 8 7 10 2 9 9 7 9 9 7 10 7 9 10 9 10 3 Sugar beet 9 9 9 0 9 9 9 9 9 10 10 9 9 9 9 9 7 9 9 3 10 10 10 10 Velvetleaf -- -- -- 3 6 2 3 5 6 10 8 5 5 5 3 7 5 9 6 0 7 6 8 6 Wheat 3 3 0 0 0 0 0 2 0 7 0 6 6 3 2 0 0 0 0 0 7 3 9 3 Wild buckwheat 7 8 7 0 8 3 7 8 8 9 9 -- -- 8 7 8 9 9 8 8 10 -- -- 10 Wild oat 5 0 2 0 0 0 0 2 3 6 4 5 7 0 0 2 0 5 3 0 5 2 8 4 Barnyardgrass -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Rice Japonica -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Umbrella sedge -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- COMPOUND Rate (8 g/ha) 125 166 167 170 172 173 203 204 205 206 207 208 209 211 212 213 214 217 218 219 225 229 PREEMERGENCE Barley Igri 0 0 0 0 0 0 2 5 4 3 4 8 0 2 0 3 2 4 0 0 0 3 Bedstraw 3 9 7 8 3 0 3 7 9 9 8 9 0 8 0 10 9 2 0 8 0 2 Blackgrass 4 7 6 3 7 8 6 8 9 9 8 8 0 7 6 7 5 7 5 4 4 0 Chickweed 7 9 9 7 -- 0 2 9 9 7 9 8 0 9 7 10 8 0 9 8 -- 0 Corn 0 5 2 6 0 3 0 5 7 9 6 7 0 5 5 10 6 2 2 0 2 0 Cotton 0 4 0 8 2 3 5 0 7 7 6 4 0 3 0 10 9 3 2 0 8 0 Crabgrass 0 7 4 6 3 3 5 7 10 5 7 8 0 7 5 5 0 2 2 0 0 2 Downy brome 0 4 4 5 0 0 7 9 7 8 7 8 0 6 2 7 7 6 5 3 0 0 Duck salad -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Giant foxtail 0 6 0 6 5 5 0 7 9 6 6 8 0 6 2 6 0 0 4 0 0 2 Lambsquarters 9 2 8 9 9 7 7 8 10 8 8 7 0 8 6 10 9 -- 7 5 7 6 Morningglory 0 4 0 7 2 0 3 6 9 7 7 8 0 0 4 9 9 0 2 0 2 0 Pigweed 5 8 6 9 5 5 7 10 9 8 8 9 0 8 3 9 9 6 7 6 3 2 Rape 5 8 4 9 0 0 8 8 9 5 3 9 0 8 0 10 10 4 0 5 0 0 Ryegrass 0 5 0 5 0 0 3 7 8 8 7 8 0 0 0 7 3 3 0 0 0 0 Sorghum 0 8 4 9 3 2 4 8 9 9 10 10 0 6 3 10 8 7 5 0 7 5 Soybean 0 2 0 6 0 0 3 3 6 6 4 4 0 3 2 8 7 0 2 2 4 0 Speedwell 7 10 0 9 8 4 0 3 7 8 0 8 0 8 5 10 3 9 0 0 6 6 Sugar beet 8 9 7 9 4 5 6 9 9 9 8 8 0 8 4 10 9 7 6 8 6 0 Velvetleaf 0 4 4 8 2 0 3 5 7 8 7 8 0 6 0 9 3 2 3 0 7 2 Wheat 0 0 0 0 0 0 3 5 4 8 7 8 0 4 0 5 0 4 3 0 0 0 Wild buckwheat 8 3 6 7 -- 3 4 9 8 8 5 7 3 8 0 9 9 2 0 7 2 0 Wild oat 0 0 0 0 0 0 2 4 4 3 3 3 0 0 0 4 3 2 0 0 0 0 Barnyardgrass -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Rice Japonica -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Umbrella sedge -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- COMPOUND Rate (8 g/ha) 230 231 232 240 241 242 243 244 245 252 254 256 258 259 261 266 267 268 269 270 271 272 PREEMERGENCE Barley Igri 0 5 2 5 3 4 2 2 8 0 4 8 0 0 7 0 6 2 0 4 4 0 Bedstraw 0 6 3 9 8 9 9 9 10 6 9 8 6 0 7 0 9 7 0 3 3 0 Blackgrass 2 8 5 9 10 9 10 10 10 9 7 9 9 7 9 3 9 3 3 9 9 9 Chickweed 3 0 0 9 9 9 9 10 8 5 9 0 9 0 7 0 0 0 0 0 2 9 Corn 0 0 3 6 9 6 10 10 9 4 -- 5 5 4 6 0 5 3 0 2 0 0 Cotton 0 5 2 3 2 5 10 5 4 0 7 2 3 5 3 0 2 3 0 7 0 2 Crabgrass 0 2 3 6 9 5 5 7 6 0 0 4 4 5 3 0 2 0 0 3 7 7 Downy brome 0 9 5 9 6 8 8 6 9 4 7 9 7 9 9 0 9 9 0 5 3 8 Duck salad -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Giant foxtail 0 0 2 4 8 4 6 5 5 0 0 5 7 3 5 0 4 0 0 2 5 8 Lambsquarters -- 0 0 10 10 8 9 9 10 7 7 4 9 8 9 8 0 6 0 5 6 0 Morningglory 0 4 5 5 5 3 9 6 7 0 9 0 2 0 2 0 3 7 0 0 2 0 Pigweed 2 3 4 8 9 8 9 8 8 2 7 5 8 5 8 0 7 0 0 7 7 8 Rape 0 0 0 9 9 -- 9 9 9 5 8 8 4 0 5 0 0 2 0 0 0 6 Ryegrass 0 0 0 5 6 6 9 7 9 0 3 9 8 6 6 0 0 0 0 3 2 2 Sorghum 0 9 9 9 7 4 10 10 9 0 6 9 4 8 9 3 9 7 0 0 0 0 Soybean 0 7 5 2 4 6 8 5 3 0 7 0 2 3 0 0 3 3 0 0 0 0 Speedwell 5 0 0 9 9 0 10 0 9 9 8 7 0 0 8 2 4 0 0 7 4 0 Sugar beet 2 2 2 9 9 9 9 9 9 2 9 8 5 8 7 1 4 6 -- 9 5 7 Velvetleaf 0 7 0 4 2 5 8 6 4 0 2 2 5 2 0 3 3 0 0 0 2 1 Wheat 2 7 3 5 5 3 5 2 3 0 0 7 3 4 5 0 0 0 0 5 5 5 Wild buckwheat 0 0 5 9 9 -- -- 9 8 3 9 9 9 6 9 -- 0 8 -- 5 6 -- Wild oat 0 0 0 4 4 3 6 0 3 0 -- 8 3 0 6 0 2 0 0 2 0 0 Barnyardgrass -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Rice Japonica -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Umbrella sedge -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- COMPOUND Rate (8 g/ha) 274 275 276 283 284 285 286 287 288 289 291 292 300 301 302 305 310 PREEMERGENCE Barley Igri 0 9 0 3 1 0 1 0 0 0 2 0 0 0 0 0 0 Bedstraw 0 8 0 9 7 3 10 9 10 2 0 0 0 2 5 4 2 Blackgrass 0 10 0 9 9 5 10 9 9 9 5 0 5 3 8 6 0 Chickweed 0 9 0 9 10 10 10 10 10 7 5 0 0 5 10 4 4 Corn 0 2 0 3 2 0 6 0 3 0 0 0 0 0 1 2 0 Cotton 0 7 0 3 3 3 9 8 6 0 1 0 -- 0 3 2 4 Crabgrass 0 7 0 3 3 0 8 3 7 0 3 0 0 0 4 2 0 Downy brome 0 9 0 6 3 0 7 5 9 4 3 0 0 0 3 0 0 Duck salad -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Giant foxtail 0 4 0 3 4 0 7 3 4 0 5 0 0 0 5 2 0 Lambsquarters 0 4 0 9 10 9 9 9 10 0 7 0 0 6 8 6 -- Morningglory 0 0 0 5 4 2 8 2 4 0 0 0 0 0 3 4 0 Pigweed 0 5 0 8 8 8 8 8 8 7 8 0 5 5 8 8 3 Rape 0 2 0 5 5 2 9 9 9 0 2 0 1 3 2 0 0 Ryegrass 0 4 0 8 0 0 7 2 2 0 3 0 0 0 0 0 0 Sorghum 0 9 0 7 3 0 9 5 3 0 2 0 0 0 2 7 0 Soybean 0 0 0 0 0 0 6 0 2 0 0 0 0 0 0 0 0 Speedwell 0 7 2 9 10 0 10 0 10 9 7 0 3 9 9 9 4 Sugar beet 0 7 0 9 6 4 10 10 10 7 6 0 0 9 8 9 9 Velvetleaf 0 0 0 4 3 2 8 0 6 0 0 0 2 0 4 3 2 Wheat 0 9 0 4 4 0 0 0 2 0 0 0 0 2 0 0 0 Wild buckwheat -- -- 0 9 9 8 7 9 9 5 0 0 0 4 8 8 5 Wild oat 0 4 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 Barnyardgrass -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Rice Japonica -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Umbrella sedge -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- COMPOUND Rate (4 g/ha) 1 3 5 11 13 14 25 26 27 28 29 30 31 34 35 36 50 51 53 58 59 60 63 64 71 77 78 81 82 POSTEMERGENCE Barley Igri 5 5 5 8 2 4 5 6 8 5 8 8 5 2 0 2 4 7 8 0 4 1 6 6 0 0 0 2 3 Bedstraw 5 9 9 0 2 2 7 10 -- 5 10 10 5 2 7 9 7 9 5 8 9 9 5 4 4 0 4 4 6 Blackgrass 5 7 7 7 3 0 8 9 7 7 9 9 5 2 7 5 8 7 8 6 6 4 8 9 0 4 3 8 9 Chickweed 0 0 8 8 5 5 8 10 10 2 10 10 -- 5 0 9 8 9 6 4 10 10 5 7 7 0 0 4 8 Corn 6 10 10 7 10 8 8 10 10 8 10 10 7 8 10 10 5 8 6 7 6 3 4 10 2 2 6 0 2 Cotton 3 3 5 3 3 0 0 2 6 4 8 8 0 0 3 6 8 10 8 6 9 9 5 8 7 0 4 4 3 Crabgrass 5 4 6 3 3 5 4 3 5 0 6 6 3 4 3 4 0 4 5 0 0 0 0 2 3 3 0 0 2 Downy brome 4 4 9 4 0 0 6 4 7 6 10 9 0 2 0 5 4 5 8 0 4 0 6 6 0 0 0 3 2 Duck salad -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- 9 9 9 6 10 9 0 8 5 0 0 0 1 Giant foxtail 6 6 6 8 6 7 7 8 8 6 10 10 7 6 6 7 4 5 7 3 0 0 7 8 0 3 5 2 6 Lambsquarters 8 10 10 9 5 5 8 10 10 9 10 10 5 2 9 10 10 10 10 -- 10 10 10 10 1 6 7 5 6 Morningglory 6 6 6 5 4 6 7 10 10 10 10 10 5 6 8 9 10 10 8 8 7 8 9 10 8 5 7 7 9 Pigweed 3 2 10 7 7 0 6 5 10 7 8 8 6 7 6 8 7 10 7 3 10 8 8 10 8 7 9 3 8 Rape 0 3 10 4 9 9 3 5 6 8 10 10 0 2 0 8 10 10 9 8 10 10 9 9 5 6 7 8 9 Ryegrass 3 0 7 4 0 0 9 9 7 6 8 6 0 2 2 5 5 8 7 0 8 2 6 6 0 0 0 0 3 Sorghum 6 7 10 6 8 7 10 10 10 10 10 10 8 7 6 10 6 8 6 5 3 3 9 9 3 6 7 9 9 Soybean 5 7 10 6 8 7 7 7 10 8 10 10 5 6 7 10 10 8 9 9 9 10 8 10 8 6 6 6 7 Speedwell 4 0 7 0 0 0 4 2 0 3 7 0 0 0 0 0 4 9 5 7 10 2 4 0 0 0 0 -- 0 Sugar beet 6 6 10 8 8 5 6 6 10 6 10 10 5 5 9 10 9 10 7 6 10 10 10 10 3 6 7 6 9 Velvetleaf 4 4 6 3 0 0 5 5 7 7 7 8 4 2 5 6 10 10 10 9 7 0 8 9 6 0 6 4 7 Wheat 4 0 9 9 3 3 6 4 7 4 8 9 2 2 2 3 4 6 9 0 0 0 6 5 0 0 0 0 0 Wild buckwheat 7 5 9 8 0 0 6 4 9 6 10 10 0 0 0 2 5 10 6 3 10 7 5 5 0 0 4 8 5 Wild oat 7 6 6 6 0 0 7 5 7 3 6 8 5 3 4 6 3 6 6 0 5 2 4 5 0 0 0 0 0 Barnyardgrass 0 0 0 1 0 0 0 6 2 8 4 0 0 0 0 0 2 7 8 6 7 2 6 8 0 0 0 0 5 Rice Japonica 2 0 6 0 0 0 1 0 0 6 5 0 0 0 0 5 0 8 0 6 8 9 5 7 7 0 0 0 3 Umbrella sedge 2 8 3 0 0 0 8 5 9 7 0 0 0 2 0 0 8 9 9 7 9 9 1 9 0 2 3 0 4
TABLE B - COMPOUND Rate (4 g/ha) 83 84 86 88 89 102 103 107 108 109 110 111 112 114 115 116 117 118 119 120 121 122 166 POSTEMERGENCE Barley Igri 3 3 3 3 3 8 7 7 3 9 9 7 5 5 2 3 0 0 9 4 5 5 5 Bedstraw 8 0 6 7 9 7 8 10 10 8 9 9 8 8 10 10 10 8 8 7 10 10 5 Blackgrass 8 9 8 8 8 8 8 9 6 10 10 10 9 9 9 8 5 5 9 10 8 9 8 Chickweed 8 6 0 4 4 5 7 10 10 5 8 5 6 3 4 9 10 0 9 9 10 10 8 Corn 5 4 0 0 5 0 0 10 10 3 8 9 7 8 7 4 0 0 9 10 10 10 9 Cotton 9 2 2 7 2 0 6 10 9 8 6 8 6 5 8 8 9 2 8 10 8 6 3 Crabgrass 5 0 0 0 0 0 0 2 0 2 2 0 0 0 0 0 0 0 0 0 0 0 4 Downy brome 0 0 0 4 0 4 5 6 0 9 9 7 5 3 0 0 0 0 8 3 5 5 2 Duck salad 2 0 0 0 4 0 0 9 8 8 9 0 0 3 0 6 5 0 6 0 3 2 8 Giant foxtail 7 2 3 2 0 2 0 4 0 4 5 4 0 6 3 2 0 0 6 6 4 0 5 Lambsquarters 9 9 6 8 9 9 -- 10 10 10 10 10 9 5 2 5 0 0 10 8 9 2 10 Morningglory 9 6 6 7 10 7 8 10 10 3 10 10 10 7 9 9 10 7 10 10 10 10 7 Pigweed 10 6 0 0 0 7 8 10 8 8 8 10 10 3 0 6 4 0 9 10 10 10 2 Rape 6 9 7 8 10 9 6 10 9 9 10 10 10 9 9 9 9 8 9 10 10 10 7 Ryegrass 0 0 0 2 0 0 0 10 5 9 10 5 6 7 0 7 2 2 8 3 9 6 3 Sorghum 9 9 9 7 7 8 9 9 8 9 8 9 9 7 8 8 7 0 9 10 9 8 9 Soybean 8 4 5 8 9 4 7 10 10 6 10 9 8 7 8 8 9 0 9 10 10 10 8 Speedwell -- 2 0 8 0 -- -- -- -- 6 8 4 7 9 2 10 0 -- 9 0 10 0 6 Sugar beet 9 8 8 8 8 9 9 10 10 8 9 9 8 3 5 9 9 3 9 10 10 10 9 Velvetleaf 8 3 4 2 3 0 4 10 5 7 8 8 7 7 8 9 5 0 9 10 9 5 7 Wheat 2 0 2 2 0 8 6 7 0 9 9 5 3 4 3 0 0 0 9 4 5 5 5 Wild buckwheat 8 4 5 5 2 4 4 9 10 8 -- 7 7 5 7 9 9 5 10 7 8 9 5 Wild oat 0 3 0 0 0 3 5 8 6 9 9 6 4 4 0 3 3 0 4 2 9 6 6 Barnyardgrass 6 2 7 0 0 0 0 6 5 8 8 6 5 7 4 4 0 2 0 0 6 2 0 Rice Japonica 6 2 0 0 2 0 0 8 8 8 7 7 8 8 6 6 5 4 0 2 7 0 4 Umbrella sedge 8 0 0 0 2 0 0 9 8 7 8 7 3 6 8 8 8 0 9 8 7 3 9 COMPOUND Rate (4 g/ha) 167 170 172 173 203 204 205 206 207 208 211 212 213 214 217 218 219 225 229 230 231 232 POSTEMERGENCE Barley Igri 7 3 8 9 5 9 10 9 6 5 8 7 3 3 7 4 0 6 6 5 5 4 Bedstraw 6 9 6 8 6 6 9 7 7 7 6 7 10 9 3 5 8 4 9 6 8 7 Blackgrass 8 7 10 9 7 10 10 10 9 8 8 8 7 7 6 5 5 4 9 9 9 9 Chickweed 7 9 4 3 6 9 10 8 5 7 5 5 10 10 0 7 7 8 2 0 0 8 Corn 10 10 7 8 9 9 10 10 9 9 8 9 9 7 7 6 6 7 8 8 7 7 Cotton 5 8 5 4 3 3 6 3 4 6 3 6 8 7 4 4 3 3 0 0 5 2 Crabgrass 0 9 5 8 7 9 10 8 8 6 2 3 3 0 4 0 0 5 0 0 2 1 Downy brome 8 0 7 9 5 8 9 9 8 3 8 5 6 5 7 6 3 4 0 3 7 7 Duck salad 0 8 0 0 3 5 9 1 9 9 8 7 6 8 0 0 0 0 0 0 0 0 Giant foxtail 3 10 7 9 5 7 10 8 10 8 6 6 4 0 5 4 0 5 4 4 4 0 Lambsquarters 10 10 9 9 9 10 10 10 8 10 10 10 10 10 9 10 8 10 7 8 -- 10 Morningglory 4 8 8 7 8 7 10 7 6 10 6 10 8 10 7 7 0 6 8 8 8 7 Pigweed 4 10 8 8 8 10 10 10 4 10 5 3 9 7 3 5 6 8 1 6 9 3 Rape 9 10 0 0 8 10 10 9 9 8 6 8 10 10 8 5 6 9 0 2 8 5 Ryegrass 7 7 3 7 4 8 10 6 4 5 3 0 7 4 4 3 4 0 0 0 4 3 Sorghum 9 10 5 8 10 10 10 10 10 10 7 8 10 8 7 6 3 7 8 8 9 9 Soybean 7 8 7 8 7 9 10 9 7 5 8 6 10 10 5 7 7 6 7 3 8 6 Speedwell 0 9 9 0 5 4 0 6 0 0 4 0 9 6 0 0 0 3 0 0 -- -- Sugar beet 9 10 7 9 8 9 9 9 5 8 6 7 10 10 7 9 8 8 2 2 8 5 Velvetleaf 7 9 5 4 6 7 9 6 4 6 3 5 8 3 3 5 6 5 5 4 7 4 Wheat 5 8 7 9 3 7 8 7 7 3 7 3 3 0 6 3 0 3 3 3 7 4 Wild buckwheat 5 8 8 8 7 8 9 7 3 7 5 7 10 7 2 7 7 6 4 5 8 7 Wild oat 8 4 5 7 5 8 9 8 8 4 4 3 4 4 6 3 3 2 4 6 5 4 Barnyardgrass 0 7 0 0 1 3 7 7 2 8 7 3 2 2 0 0 1 0 0 0 0 0 Rice Japonica 0 7 0 0 8 4 8 6 8 9 6 6 6 7 7 4 2 0 0 0 0 0 Umbrella sedge 9 4 0 2 6 9 9 7 2 8 9 8 8 8 0 0 0 0 0 0 0 0 COMPOUND Rate (4 g/ha) 240 241 242 243 244 245 252 256 258 259 261 266 267 268 270 271 272 274 275 276 283 284 POSTEMERGENCE Barley Igri 9 8 10 7 5 8 6 8 8 6 7 4 6 5 9 8 9 0 7 5 9 9 Bedstraw 8 9 10 9 10 10 9 8 9 5 9 7 9 9 6 9 7 0 6 0 9 10 Blackgrass 10 10 10 10 10 9 9 9 8 8 8 9 9 9 8 9 10 2 9 4 9 9 Chickweed 9 8 10 10 10 0 0 7 9 3 7 0 2 3 4 9 9 0 5 0 9 10 Corn 10 10 10 10 10 9 9 10 10 9 10 9 8 9 10 10 10 0 10 4 9 10 Cotton 4 7 7 7 8 5 0 0 0 0 0 0 5 1 3 3 2 0 0 0 5 8 Crabgrass 6 5 8 9 7 6 0 7 7 0 0 0 0 0 7 7 7 0 7 0 7 5 Downy brome 8 8 9 9 9 6 8 9 8 8 8 5 8 6 7 9 9 0 9 3 9 9 Duck salad 5 2 4 7 0 5 0 0 0 0 0 0 0 0 0 0 0 0 0 0 5 4 Giant foxtail 8 10 9 8 7 7 5 7 10 5 10 4 0 0 5 7 10 0 9 0 8 8 Lambsquarters 9 8 10 10 4 8 0 9 10 8 8 0 7 0 8 9 9 0 6 0 8 9 Morningglory 9 10 10 9 10 10 7 9 10 5 8 9 8 8 7 8 5 0 3 4 5 10 Pigweed 10 7 10 10 8 9 5 8 8 8 8 0 8 7 10 8 8 0 8 2 9 7 Rape 9 9 10 10 9 9 8 8 9 7 9 4 8 9 8 9 8 0 9 0 10 9 Ryegrass 10 7 10 10 4 8 0 9 9 8 8 0 8 3 4 4 8 0 9 0 8 0 Sorghum 9 10 10 10 10 10 9 10 10 10 9 9 9 9 10 9 9 0 9 8 10 9 Soybean 8 8 9 9 9 8 8 5 9 7 4 8 8 9 4 7 5 0 4 0 9 8 Speedwell 0 3 6 10 0 3 0 0 0 0 0 0 5 0 0 0 0 0 0 0 3 5 Sugar beet 9 8 10 10 10 8 0 6 8 9 7 0 9 8 9 9 9 0 5 0 8 8 Velvetleaf 5 6 9 8 7 7 0 6 7 0 0 0 5 0 0 0 3 0 0 0 7 8 Wheat 8 9 9 8 4 5 5 7 7 6 7 0 6 4 9 8 8 0 8 2 9 9 Wild buckwheat 9 9 -- 9 -- 9 -- 9 8 0 9 7 5 7 9 9 9 -- 10 -- 9 -- Wild oat 9 9 10 10 9 8 4 7 8 7 7 4 6 7 8 5 9 0 8 0 10 7 Barnyardgrass 0 0 5 6 0 7 0 0 0 0 6 0 0 0 0 0 0 0 0 0 2 0 Rice Japonica 0 0 7 6 4 8 3 6 0 5 8 0 0 0 0 0 6 0 7 0 6 2 Umbrella sedge 7 7 7 6 3 7 0 6 8 0 1 0 0 0 7 3 3 0 3 0 8 7 COMPOUND Rate (4 g/ha) 285 286 287 288 289 291 300 301 302 305 310 POSTEMERGENCE Barley Igri 9 10 9 8 7 9 9 9 9 8 4 Bedstraw 10 10 9 10 9 8 8 8 9 7 5 Blackgrass 9 9 9 9 10 10 9 9 9 9 6 Chickweed 10 10 10 10 9 7 8 9 9 9 -- Corn 10 10 10 10 9 9 7 8 10 8 7 Cotton 8 9 8 3 5 3 2 0 5 0 0 Crabgrass 3 8 8 0 5 8 5 4 8 5 0 Downy brome 9 9 5 8 8 9 7 8 9 7 0 Duck salad 0 1 1 8 0 0 0 0 0 0 0 Giant foxtail 9 9 10 8 7 8 8 7 9 7 5 Lambsquarters 9 10 9 10 8 9 9 9 9 9 4 Morningglory 10 10 10 10 7 7 2 6 9 4 9 Pigweed 8 8 10 8 7 8 5 7 8 7 2 Rape 9 10 10 10 0 9 7 9 9 9 9 Ryegrass 0 9 4 4 0 8 6 4 4 0 0 Sorghum 10 10 10 10 9 9 7 8 9 9 8 Soybean 9 10 10 9 8 7 7 8 10 6 8 Speedwell 0 10 0 8 0 0 -- 10 -- 6 8 Sugar beet 9 10 10 9 8 7 9 9 10 9 9 Velvetleaf 10 8 0 8 0 4 0 0 6 0 6 Wheat 9 9 4 8 7 6 7 5 9 5 0 Wild buckwheat 10 -- 10 10 5 9 8 3 6 -- 8 Wild oat 5 9 5 8 5 8 7 8 9 4 2 Barnyardgrass 0 4 4 7 0 0 3 0 2 2 0 Rice Japonica 2 2 2 7 0 0 0 2 -- 4 0 Umbrella sedge 0 0 0 7 0 0 0 0 2 0 0 COMPOUND Rate (4 g/ha) 1 3 5 11 13 14 25 26 27 28 29 30 31 34 35 36 50 51 53 58 59 60 63 64 71 77 78 81 82 PREEMERGENCE Barley Igri 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 5 6 0 5 0 5 5 0 0 0 2 3 Bedstraw 2 4 7 4 4 3 2 2 0 2 5 2 0 0 3 8 7 10 8 7 9 9 6 9 8 0 4 0 8 Blackgrass 4 4 0 2 0 0 4 4 4 3 4 2 0 0 4 5 7 7 9 5 7 4 9 9 3 2 3 7 9 Chickweed 0 6 6 8 8 7 0 2 -- -- 9 5 0 3 6 8 9 10 9 7 9 10 5 7 7 0 3 0 9 Corn 0 2 0 4 0 0 4 2 4 2 4 4 0 0 0 0 0 7 0 0 4 2 3 9 0 0 0 -- -- Cotton 0 2 5 0 3 0 4 5 6 5 8 7 0 0 0 6 4 9 7 0 9 9 4 8 4 0 -- -- -- Crabgrass 0 3 4 0 0 0 2 6 4 4 5 8 0 0 0 2 5 8 7 3 0 0 5 8 0 0 4 -- -- Downy brome 2 0 6 0 0 0 0 0 0 3 0 0 0 0 3 3 3 7 7 2 6 3 9 8 0 0 0 4 4 Duck salad -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Giant foxtail 0 0 0 0 0 0 0 3 2 2 7 4 2 0 0 3 4 7 7 0 0 0 8 8 0 0 0 -- -- Lambsquarters 4 6 10 4 7 6 0 5 0 3 5 5 5 6 8 8 9 10 9 5 10 8 9 10 7 0 2 8 9 Morningglory 0 3 3 0 0 0 4 4 1 3 4 3 0 0 0 3 7 9 3 0 8 9 6 8 5 0 6 -- -- Pigweed 0 5 5 0 2 0 7 7 7 7 8 9 0 0 3 8 10 10 9 6 8 9 9 9 8 4 7 -- -- Rape 2 3 0 0 6 4 4 2 2 4 4 4 0 0 0 4 7 9 9 8 10 9 9 9 6 4 6 6 9 Ryegrass 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 5 9 7 2 8 6 4 6 0 0 0 0 4 Sorghum 0 2 6 0 0 2 5 3 3 4 10 4 0 0 2 3 4 9 6 4 7 5 9 9 0 3 3 -- -- Soybean 0 0 2 0 0 0 2 0 2 0 5 2 0 0 0 2 4 7 3 0 6 5 2 6 4 0 3 -- -- Speedwell 0 3 10 4 7 5 7 7 0 4 9 0 0 0 5 4 9 10 10 3 10 5 5 5 0 0 0 6 9 Sugar beet 5 6 9 3 7 3 0 4 0 5 4 5 0 4 8 8 8 9 9 8 9 10 9 9 8 0 8 8 9 Velvetleaf 0 0 3 0 0 0 3 5 2 3 8 2 0 0 0 2 4 9 7 4 9 6 7 9 8 0 4 -- -- Wheat 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 5 6 0 3 0 5 5 0 0 0 0 3 Wild buckwheat 5 4 7 0 3 0 0 0 0 2 4 5 0 0 7 7 8 9 8 2 8 8 8 7 4 0 4 4 8 Wild oat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 5 3 0 5 3 0 2 0 0 0 3 0 Barnyardgrass -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Rice Japonica -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Umbrella sedge -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- COMPOUND Rate (4 g/ha) 83 84 86 88 89 102 103 107 108 109 110 111 112 114 115 116 117 118 119 120 121 122 166 PREEMERGENCE Barley Igri 0 0 0 3 0 3 3 4 0 6 5 0 0 0 0 4 0 0 7 3 6 0 0 Bedstraw 9 0 6 4 9 2 8 10 10 8 6 3 8 8 7 9 9 0 0 2 4 8 0 Blackgrass 9 3 8 8 8 4 8 9 9 9 9 8 7 8 7 8 5 4 9 9 3 5 6 Chickweed 9 0 4 7 7 3 6 9 9 8 9 7 8 8 7 8 8 4 9 9 9 9 8 Corn -- 5 0 0 0 0 0 10 8 4 6 2 0 6 0 6 0 0 7 4 10 7 4 Cotton -- 4 3 2 0 0 3 10 9 6 4 4 3 2 0 9 8 0 7 6 9 8 3 Crabgrass -- 0 1 0 1 0 0 7 6 4 3 0 0 3 0 5 0 0 5 3 0 2 6 Downy brome 3 0 0 3 4 0 4 7 2 8 5 0 0 4 0 5 0 0 8 2 5 5 0 Duck salad -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Giant foxtail -- 0 0 0 2 0 0 7 4 4 6 0 0 6 0 5 0 0 6 3 0 0 4 Lambsquarters 8 3 -- 0 8 3 1 9 9 8 9 9 9 8 5 9 8 5 10 9 8 8 0 Morningglory -- 2 2 2 3 0 3 9 8 6 5 5 5 7 6 9 9 2 8 7 9 7 2 Pigweed -- 0 7 2 7 7 8 9 9 9 9 8 8 8 7 8 8 5 9 8 8 7 8 Rape 8 0 6 7 9 6 7 9 9 9 8 5 5 8 5 9 8 3 9 7 8 10 4 Ryegrass -- 0 3 0 0 0 0 9 5 7 6 0 0 6 0 7 2 0 0 0 3 0 2 Sorghum -- 9 9 5 6 5 7 9 9 6 9 0 3 7 4 8 5 0 7 2 8 7 4 Soybean -- 4 2 4 1 0 0 9 7 5 4 0 1 0 0 7 3 0 7 4 7 5 0 Speedwell 7 6 8 8 7 3 3 10 2 9 9 3 9 8 7 10 3 7 10 8 8 0 9 Sugar beet 9 -- 8 9 8 7 9 10 10 9 9 9 9 9 6 9 9 3 10 8 9 9 0 Velvetleaf -- 0 6 2 2 4 5 10 8 5 3 4 3 6 5 9 6 0 5 2 8 0 2 Wheat 0 0 0 0 0 0 0 5 0 6 5 3 0 0 0 0 0 0 6 0 8 3 0 Wild buckwheat -- 0 7 3 6 2 8 9 9 -- -- 6 -- 8 8 8 8 -- 10 8 9 9 3 Wild oat 2 0 0 0 0 0 0 3 0 4 4 0 0 2 0 4 2 0 4 0 0 0 0 Barnyardgrass -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Rice Japonica -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Umbrella sedge -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- --
TABLE B - COMPOUND Rate (4 g/ha) 167 170 172 173 203 204 205 206 207 208 211 212 213 214 217 218 219 225 229 230 231 232 PREEMERGENCE Barley Igri 0 0 0 0 0 3 0 0 2 7 0 0 2 0 3 0 0 0 0 0 0 2 Bedstraw 2 8 0 0 0 3 8 8 6 8 5 0 9 9 0 0 3 0 0 0 3 2 Blackgrass 2 3 5 8 5 8 8 8 4 8 4 4 6 3 6 5 0 0 0 0 3 5 Chickweed 8 7 0 0 2 8 9 5 3 8 8 7 9 8 0 8 6 2 0 0 0 0 Corn 2 0 0 -- 0 4 0 7 3 0 3 5 8 0 0 0 0 0 0 0 0 3 Cotton 0 7 0 0 3 0 7 5 4 3 0 0 10 8 3 0 0 4 0 0 3 0 Crabgrass 4 2 0 0 3 6 8 4 5 7 5 3 3 0 0 0 0 0 0 0 0 0 Downy brome 0 0 0 0 6 5 6 7 5 7 4 0 7 6 5 5 2 0 0 0 6 2 Duck salad -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Giant foxtail 0 2 3 2 0 5 7 5 3 7 3 0 4 0 0 2 0 0 0 0 0 0 Lambsquarters 2 8 9 0 3 8 10 3 3 7 7 -- 9 8 6 -- 2 0 6 3 0 0 Morningglory 0 7 0 0 0 4 7 5 6 7 0 2 8 8 0 0 0 0 0 0 1 2 Pigweed 6 9 5 5 4 9 9 7 5 9 7 3 9 9 2 5 5 0 0 0 0 0 Rape 4 8 0 0 6 5 8 3 2 8 5 0 10 8 3 0 3 0 0 0 0 0 Ryegrass 0 0 0 0 0 4 5 8 4 7 0 0 5 0 0 0 0 0 0 0 0 0 Sorghum 4 8 2 0 3 6 7 9 9 10 3 0 10 7 5 3 0 3 4 0 9 9 Soybean 0 2 0 0 0 0 5 4 0 2 0 0 7 6 0 0 0 2 0 0 4 2 Speedwell 0 9 7 4 0 0 3 3 0 7 7 0 9 3 0 0 0 -- 2 4 0 0 Sugar beet 4 9 4 2 2 7 8 8 2 8 7 4 9 9 4 5 7 4 0 0 0 2 Velvetleaf 2 7 0 0 0 3 6 7 4 8 5 0 8 0 0 0 0 2 2 0 3 0 Wheat 0 0 0 0 0 3 3 6 2 7 4 0 4 0 3 2 0 0 0 0 2 2 Wild buckwheat 4 6 0 -- 1 8 8 7 3 7 3 0 9 8 0 0 3 2 0 0 0 3 Wild oat 0 0 0 0 0 3 3 0 2 2 0 0 2 0 0 0 0 0 0 0 0 0 Barnyardgrass -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Rice Japonica -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Umbrella sedge -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- COMPOUND Rate (4 g/ha) 240 241 242 243 244 245 252 256 258 259 261 266 267 268 270 271 272 274 275 276 283 284 PREEMERGENCE Barley Igri 4 0 0 0 0 3 0 4 0 0 5 0 4 0 3 2 0 0 7 0 0 0 Bedstraw 5 6 7 8 8 9 4 3 6 0 5 0 5 0 0 0 0 0 5 0 8 7 Blackgrass 9 10 9 9 10 9 6 9 9 6 9 3 8 3 6 8 6 0 9 0 9 6 Chickweed 4 9 9 8 10 8 5 0 7 0 0 0 0 0 0 0 7 0 0 0 9 10 Corn 4 8 4 10 8 6 0 2 5 0 4 0 0 0 0 0 0 0 0 0 3 0 Cotton 0 1 4 7 5 4 0 0 0 -- 2 0 0 0 3 0 0 0 2 0 2 2 Crabgrass 4 5 3 3 4 5 0 0 3 0 2 0 2 0 0 3 4 0 3 0 0 0 Downy brome 4 5 7 5 4 9 3 7 6 4 6 0 8 6 0 0 3 0 9 0 2 0 Duck salad -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Giant foxtail 1 3 2 4 3 4 0 3 4 0 4 0 4 0 0 2 8 0 2 0 0 1 Lambsquarters 9 9 8 8 9 9 -- 4 9 8 -- 3 0 0 -- 6 0 0 3 0 9 9 Morningglory 4 2 2 8 4 5 0 0 0 0 0 0 2 2 0 0 0 0 0 0 3 4 Pigweed 7 8 8 8 7 8 0 0 7 3 7 0 6 0 2 3 2 0 3 0 8 8 Rape 6 6 3 9 7 8 3 4 3 0 3 0 0 0 0 0 2 0 2 0 -- 3 Ryegrass 4 4 3 6 2 2 0 4 5 4 4 0 0 0 0 0 0 0 3 0 3 0 Sorghum 3 4 2 10 10 9 0 8 4 7 8 3 8 5 0 0 0 0 4 0 2 0 Soybean 0 1 6 7 0 2 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 Speedwell 8 9 0 9 0 9 7 7 0 0 3 2 -- 0 0 3 0 0 0 0 -- 9 Sugar beet 8 9 7 9 9 9 1 0 5 2 6 0 1 0 2 -- 0 0 7 0 6 6 Velvetleaf 2 2 2 8 4 0 0 0 3 0 0 2 0 0 0 2 0 0 0 0 4 2 Wheat 3 5 0 4 0 3 0 6 3 0 5 0 0 0 3 0 0 0 4 0 0 0 Wild buckwheat 9 9 -- 9 8 7 0 9 9 -- 9 7 -- 8 5 6 5 -- -- 0 9 8 Wild oat 4 0 0 3 0 0 0 5 2 0 4 0 0 0 0 0 0 0 0 0 0 0 Barnyardgrass -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Rice Japonica -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Umbrella sedge -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- COMPOUND Rate (4 g/ha) 285 286 287 288 289 291 300 301 302 305 310 PREEMERGENCE Barley Igri 0 0 0 0 0 0 0 0 0 0 0 Bedstraw -- 9 8 10 0 0 0 2 4 0 2 Blackgrass 4 4 5 7 8 3 3 2 4 3 0 Chickweed 9 9 10 9 7 2 0 5 5 0 0 Corn 0 5 0 0 0 0 0 0 0 2 0 Cotton 2 7 4 2 0 0 0 0 2 0 0 Crabgrass 0 6 0 4 0 2 0 0 0 0 0 Downy brome 0 4 0 8 0 2 0 0 0 0 0 Duck salad -- -- -- -- -- -- -- -- -- -- -- Giant foxtail 0 7 0 0 0 3 0 0 2 0 0 Lambsquarters 5 9 9 10 0 5 0 4 7 0 0 Morningglory 0 7 0 2 0 0 0 0 0 0 0 Pigweed 7 8 8 8 7 6 3 0 7 5 0 Rape 0 9 9 8 0 2 0 0 0 0 0 Ryegrass 0 4 0 0 0 0 0 0 0 0 0 Sorghum 0 8 2 0 0 2 0 0 0 5 0 Soybean 0 4 0 0 0 0 0 0 0 0 0 Speedwell 0 10 0 10 9 2 0 5 8 0 4 Sugar beet 4 9 9 8 5 3 0 7 6 4 2 Velvetleaf 0 8 0 3 0 0 0 0 0 2 0 Wheat 0 0 0 0 0 0 0 2 0 0 0 Wild buckwheat 7 4 8 8 5 0 0 4 7 7 -- Wild oat 0 0 0 0 0 0 0 0 0 0 0 Barnyardgrass -- -- -- -- -- -- -- -- -- -- -- Rice Japonica -- -- -- -- -- -- -- -- -- -- -- Umbrella sedge -- -- -- -- -- -- -- -- -- -- -- COMPOUND Rate (2 g/ha) 25 26 27 28 29 30 31 34 36 107 204 205 206 207 240 241 242 243 244 245 272 283 284 285 POSTEMERGENCE Barley Igri 3 5 6 5 6 7 4 0 2 4 7 10 7 4 8 6 9 6 4 8 5 9 8 8 Bedstraw 6 6 8 4 10 7 5 0 8 10 5 5 4 6 7 6 8 9 9 9 0 8 9 10 Blackgrass 7 9 7 7 6 5 4 0 4 9 10 10 10 9 9 9 9 10 9 9 9 9 9 9 Chickweed 5 6 9 0 9 10 0 2 8 10 8 10 6 5 5 6 8 9 10 0 9 9 10 10 Corn 7 10 10 7 10 10 6 7 10 10 8 9 10 7 10 9 10 10 10 9 9 9 10 10 Cotton 0 2 4 2 7 6 0 0 3 10 0 4 2 0 1 3 2 5 8 4 0 3 7 6 Crabgrass 3 2 4 0 5 5 0 3 3 0 8 10 7 7 5 4 7 8 4 4 6 5 3 0 Downy brome 4 2 4 6 9 5 0 0 4 3 8 9 9 7 5 5 9 9 8 4 7 7 5 6 Duck salad -- -- -- -- -- -- -- -- -- 7 0 9 0 3 0 0 0 5 0 2 0 2 0 0 Giant foxtail 6 7 7 6 10 9 6 5 7 2 6 9 7 7 5 8 9 8 6 6 10 7 6 9 Lambsquarters 6 10 10 8 10 10 5 0 8 10 10 10 9 8 8 7 10 10 3 8 7 8 9 9 Morningglory 7 8 9 10 8 10 4 5 7 10 7 10 6 5 8 8 8 8 9 8 3 4 5 10 Pigweed 5 4 8 6 7 7 5 6 7 10 10 10 9 3 9 7 10 10 7 8 7 9 7 8 Rape 3 2 6 7 7 8 0 0 6 9 5 9 9 7 7 9 10 8 8 9 3 9 7 6 Ryegrass 4 6 3 5 7 0 0 0 2 8 6 10 6 -- 7 2 5 10 0 4 2 3 0 0 Sorghum 10 9 10 9 10 10 8 6 10 8 10 10 10 10 9 10 10 10 10 10 9 9 9 9 Soybean 6 6 10 7 10 10 3 3 8 10 8 10 7 6 5 8 9 9 8 6 4 6 8 9 Speedwell 2 0 0 2 5 0 0 0 0 -- -- 0 3 0 0 2 0 9 0 0 0 0 3 0 Sugar beet 5 4 6 6 10 10 4 3 9 10 8 7 9 4 9 8 9 10 10 -- 6 6 8 9 Velvetleaf 4 4 5 5 7 7 3 0 5 9 7 8 3 2 5 6 6 7 6 5 0 7 8 10 Wheat 5 4 3 4 6 8 0 0 2 3 4 7 6 4 7 5 7 5 3 4 4 9 8 5 Wild buckwheat 6 -- 7 5 9 9 0 0 2 9 6 8 0 3 9 -- 9 6 -- 9 9 8 8 -- Wild oat 5 4 5 0 4 6 0 0 4 6 7 9 7 6 8 8 9 10 7 4 5 8 6 2 Barnyardgrass 0 0 2 7 1 0 0 0 0 4 0 5 0 0 0 0 3 3 0 5 0 0 0 0 Rice Japonica 0 0 0 5 0 0 0 0 0 7 3 3 3 6 0 0 6 2 0 7 1 2 0 1 Umbrella sedge 2 5 8 7 0 0 0 2 -- 8 7 9 3 0 0 3 7 3 0 0 2 8 5 0 COMPOUND Rate (2 g/ha) 286 287 288 291 POSTEMERGENCE Barley Igri 9 9 8 7 Bedstraw 10 8 10 5 Blackgrass 9 9 8 10 Chickweed 9 10 9 5 Corn 10 9 9 9 Cotton 5 5 3 0 Crabgrass 7 7 0 5 Downy brome 8 0 6 6 Duck salad 0 0 2 0 Giant foxtail 9 7 7 7 Lambsquarters 9 6 8 9 Morningglory 7 9 8 5 Pigweed 6 10 7 7 Rape 9 10 9 7 Ryegrass 2 0 2 5 Sorghum 10 10 10 8 Soybean 10 9 8 5 Speedwell 9 0 7 0 Sugar beet 10 10 9 7 Velvetleaf 6 0 8 2 Wheat 9 3 7 6 Wild buckwheat 9 10 10 -- Wild oat 9 0 4 5 Barnyardgrass 0 0 2 0 Rice Japonica 1 2 3 0 Umbrella sedge 0 0 0 0 COMPOUND Rate (2 g/ha) 25 26 27 28 29 30 31 34 36 107 204 205 206 207 240 241 242 243 244 245 272 283 284 285 PREEMERGENCE Barley Igri 0 0 0 0 0 0 0 0 0 3 2 0 -- 0 2 0 0 0 0 3 0 0 0 0 Bedstraw 0 0 0 0 3 0 0 0 7 10 0 7 5 2 3 2 6 7 7 9 0 5 7 2 Blackgrass 0 0 0 2 3 0 0 0 3 9 7 8 7 0 8 5 9 7 7 8 4 6 5 2 Chickweed 0 0 -- 5 7 4 0 0 6 9 8 8 5 2 0 6 9 8 9 5 3 9 9 7 Corn 2 0 4 2 4 2 0 0 0 10 2 0 3 3 3 2 3 10 5 5 0 3 0 0 Cotton 3 5 5 4 5 5 0 0 6 10 0 4 3 3 0 0 4 6 2 3 0 0 0 0 Crabgrass 0 3 3 2 4 7 0 0 0 7 4 7 3 3 0 3 0 0 0 2 3 0 0 0 Downy brome 0 0 0 0 0 0 0 0 0 5 2 4 -- 3 3 0 0 0 3 5 3 0 0 0 Duck salad -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Giant foxtail 0 2 0 0 3 3 0 0 0 5 3 5 3 0 0 0 0 0 0 3 2 0 0 0 Lambsquarters 0 2 0 2 2 0 2 3 7 9 7 7 0 3 8 7 7 8 3 9 0 9 0 -- Morningglory 3 2 0 3 2 0 0 0 0 9 3 6 3 0 0 0 2 7 0 2 0 0 3 0 Pigweed 7 2 4 3 4 8 0 0 3 9 6 8 6 0 5 8 3 8 7 7 0 8 5 2 Rape 3 0 0 2 1 0 0 0 3 8 2 5 -- 0 5 4 3 5 4 3 0 3 3 0 Ryegrass 0 0 0 0 0 0 0 0 0 9 0 3 -- 2 2 4 0 2 2 0 0 0 0 0 Sorghum 4 2 0 4 5 4 0 0 0 9 4 4 9 8 2 0 0 10 9 6 0 0 0 0 Soybean 2 0 2 0 4 0 0 0 0 8 0 4 3 0 0 0 2 5 0 0 0 0 0 0 Speedwell 4 2 0 0 8 0 0 0 3 10 0 0 3 0 5 4 0 8 0 9 0 9 7 0 Sugar beet 0 0 0 3 4 4 0 3 7 10 7 8 7 2 8 8 7 9 9 8 0 -- 6 3 Velvetleaf 2 4 0 0 4 0 0 0 0 9 3 3 5 0 0 0 0 7 2 0 0 4 0 0 Wheat 0 0 0 0 0 0 0 0 0 3 2 0 -- 0 2 2 0 0 0 0 0 0 0 0 Wild buckwheat 0 0 0 0 3 0 0 0 5 8 7 3 7 3 9 9 -- 4 -- 7 -- 4 8 4 Wild oat 0 0 0 0 0 0 0 0 0 0 2 0 -- 0 3 0 0 0 0 0 0 0 0 0 Barnyardgrass -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Rice Japonica -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- Umbrella sedge -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- COMPOUND Rate (2 g/ha) 286 287 288 291 PREEMERGENCE Barley Igri 0 0 0 0 Bedstraw 9 6 4 0 Blackgrass 3 3 6 0 Chickweed 9 9 9 0 Corn 4 0 0 0 Cotton 6 3 0 0 Crabgrass 3 0 0 0 Downy brome 4 0 5 0 Duck salad -- -- -- -- Giant foxtail 5 0 0 0 Lambsquarters -- 9 8 0 Morningglory 5 0 0 0 Pigweed 7 7 8 2 Rape 2 3 5 0 Ryegrass 2 0 0 0 Sorghum 4 0 0 2 Soybean 3 0 0 0 Speedwell 8 0 10 0 Sugar beet 6 8 7 0 Velvetleaf 6 0 2 0 Wheat 0 0 0 0 Wild buckwheat 4 5 2 0 Wild oat 0 0 0 0 Barnyardgrass -- -- -- -- Rice Japonica -- -- -- -- Umbrella sedge -- -- -- --
TEST C
Plastic pots were partially filed with silt loam soil. The soil was then saturated with water. Japonica rice (Oryza sativa) seedlings at the 2.0 and 2.5 leaf stage, seeds selected from barnyardgrass (Echinochloa crus-galli), duck salad (Heteranthera limosa), umbrella sedge (Cyperus difformis), and tubers selected from arrowhead (Safittaria spp.), waterchestnut (Eleocharis spp.), were planted into this soil. After planting, water levels were raised to 3 cm above the soil surface and maintained at this level throughout the test. Chemical treatments were formulated in a non-phytotoxic solvent and applied directly to the paddy water. Treated plants and controls were maintained in a greenhouse for approximately 21 days, after which all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table C, are reported on a 0 to 10 scale where 0 is no effect and 10 is complete control. A dash (-) response means no test result.
TABLE C__________________________________________________________________________ COMPOUND COMPOUND COMPOUNDRate (64 g/ha) 6 58 Rate (16 g/ha) 6 27 58 205 Rate (4 g/ha) 6 27 58 205__________________________________________________________________________PADDY PADDY PADDYBarnyardgrass 5 9 Arrowhead -- -- -- 7 Arrowhead -- -- -- 3Duck salad -- 10 Barnyardgrass 0 2 6 10 Barnyardgrass 0 2 0 9Japonica rice 8 8 Duck salad -- 10 10 -- Duck salad -- 10 9 --Umbrella sedge 9 9 Japonica rice 6 6 6 7 Japonica rice 1 1 4 7Waterchestnut 8 8 Umbrella sedge 7 9 9 9 Umbrella sedge 2 9 9 9 Waterchestnut 4 6 7 8 Waterchestnut 3 4 6 8__________________________________________________________________________ COMPOUND COMPOUND COMPOUNDRate (32 g/ha) 6 27 58 205 Rate (8 g/ha) 6 27 58 205 Rate (2 g/ha) 27 205__________________________________________________________________________PADDY PADDY PADDYArrowhead -- -- -- 8 Arrowhead -- -- -- 5 Arrowhead -- 1Barnyardgrass 3 4 5 10 Barnyardgrass 0 2 4 10 Barnyardgrass 0 4Duck salad -- 10 10 -- Duck salad -- 10 10 -- Duck salad 3 --Japonica rice 7 8 7 8 Japonica rice 5 5 5 7 Japonica rice 0 5Umbrella sedge 8 9 9 10 Umbrella sedge 5 9 9 9 Umbrella sedge 0 9Waterchestnut -- 7 8 8 Waterchestnut 3 5 6 8 Waterchestnut 2 5__________________________________________________________________________
TEST D
Compounds evaluated in this test were formulated in a non-phytoxic solvent and applied to the soil surface before plant seedlings emerged (preemergence application) and to plants that were in the one-to-four leaf stage (postemergence application). A sandy loam soil was used for the preemergence test while a mixture of sandy loam soil and greenhouse potting mix in a 60:40 ratio was used for the postemergence test. Test compounds were applied within approximately one day after planting seeds for the preemergence test. Plantings of these crops and weed species were adjusted to produce plants of appropriate size for the postemergence test. All plant species were grown using normal greenhouse practices. Crop and weed species include winter barley (Hordeum vulgare cv. `Igri`), bedstraw (Galium aparine), blackgrass (Alopecurus myosuroides), chickweed (Stellaria media), downy brome (Bromus tectorum), field violet (Viola arvensis), green foxtail (Setaria viridis), kochia (Kochia scoparia), lambsquarters (Chenopodium album), Persian speedwell (Veronica persica, rape (Brassica napus cv. `Jet Neuf`), ryegrass (Lolium multiflorum), sugar beet (Beta vulgaris cv. `US1`), sunflower (Helianthus annuus cv. `Russian Giant`), spring wheat (Triticum aestivum cv. `ERA`), winter wheat (Triticum aestivum cv. `Talent`), wild buckwheat (Polygonum convolvulus), wild mustard (Sinapis arvensis), wild oat (Arena fatua), and wild radish (Raphanus raphanistrum). Blackgrass and wild oat were treated postemergence at two growth stages. The first stage (1) was when the plants had two to three leaves. The second stage (2) was when the plants had approximately four leaves or in the initial stages of tillering. Treated plants and untreated controls were maintained in a greenhouse for approximately 21 to 28 days, after which all treated plants were compared to untreated controls and visually evaluated. Plant response ratings, summarized in Table D, are based upon a 0 to 10 scale where 0 is no effect and 10 is complete control. A dash response (-) means no test result.
TABLE D__________________________________________________________________________ COMPOUNDRate (250 g/ha) 36__________________________________________________________________________PREEMERGENCEBlackgrass (1) 10Blackgrass (2) 10Chickweed 10Downy brome 10Field violet 10Galium (1) 10Green foxtail 10Kochia 10Lambsquarters 10Persn Speedwell 9Rape 10Ryegrass 10Sugar beet 10Sunflower 10Wheat (Spring) 10Wheat (Winter) 10Wild buckwheat 10Wild mustard 10Wild oat (1) 10Wild oat (2) 10Wild radish 10Winter Barley 10__________________________________________________________________________ COMPOUNDRate (125 g/ha) 36 59 60 83 89 107 108 214 229 230 232 244 252 269 288 289__________________________________________________________________________POSTEMERGENCEBlackgrass (1) -- 10 7 10 10 10 7 10 7 8 10 10 10 4 10 10Blackgrass (2) -- 7 10 9 10 6 10 7 9 10 10 10 4 10 10Chickweed -- 10 10 10 8 10 10 10 7 6 9 10 4 0 10 10Downy brome -- 7 7 5 3 7 5 10 7 9 10 10 10 5 10 10Field violet -- 10 9 8 2 10 10 10 6 8 8 10 18 0 9 6Galium (1) -- 10 10 10 9 10 10 10 9 9 10 10 10 4 10 9Galium (2) -- 10 10 10 8 10 10 10 9 9 10 10 10 3 10 10Green foxtail -- 9 7 9 5 10 5 8 6 9 5 10 10 3 10 10Kochia -- 10 10 10 2 10 10 10 3 6 4 6 4 6 10 10Lambsquarters -- 8 6 7 5 10 4 6 7 10 3 7 4 0 10 8Persn Speedwell -- 10 3 0 2 10 0 4 0 0 3 2 4 0 7 4Rape -- 10 10 10 10 10 10 10 10 10 10 10 10 7 10 7Ryegrass -- 10 8 7 4 10 10 10 5 2 10 10 6 3 9 9Sugar beet -- 10 10 10 9 10 10 10 6 8 9 10 5 2 10 10Sunflower -- 10 10 10 10 10 10 10 10 10 10 10 10 6 10 10Wheat (Spring) -- 6 4 7 3 8 5 5 7 6 10 10 8 2 10 10Wheat (Winter) -- 5 3 6 3 7 4 5 8 7 10 10 8 2 10 10Wild buckwheat -- 10 10 8 4 10 10 10 6 7 5 10 3 10 10 6Wild mustard -- 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10Wild oat (1) -- 10 8 4 2 10 8 10 10 10 10 10 9 3 10 10Wild oat (2) -- 9 8 3 2 10 7 10 10 10 10 10 8 2 10 10Wild radish -- 10 10 10 10 10 10 10 9 9 10 10 10 9 10 10Winter Barley -- 9 7 7 4 9 7 9 10 10 10 10 8 4 10 10__________________________________________________________________________ COMPOUNDRate (125 g/ha) 36 59 60 83 89 107 108 214 229 230 232 244 252 269 288 289__________________________________________________________________________PREEMERGENCEBlackgrass (1) 10 10 9 9 8 10 8 9 6 8 8 10 9 2 9 9Blackgrass (2) 10 10 9 10 7 10 8 8 8 7 6 10 9 2 8 9Chickweed 10 10 10 10 10 10 10 10 10 9 8 10 10 4 10 10Downy brome 10 9 8 6 2 9 8 10 10 8 10 10 9 3 8 9Field violet 10 10 10 10 10 10 10 10 8 9 5 10 10 0 10 9Galium (1) 10 10 10 10 10 10 10 10 10 9 8 10 8 2 10 9Galium (2) -- 10 10 10 10 10 10 10 -- 8 8 10 9 2 10 9Green foxtail 10 10 10 10 6 10 8 10 6 3 8 10 7 0 8 10Kochia 9 10 10 10 8 10 10 9 4 2 4 10 3 0 10 8Lambsquarters 10 10 10 10 10 10 10 10 7 9 2 10 10 0 10 6Persn Speedwell 7 10 9 10 8 10 10 8 5 4 5 8 9 0 10 8Rape 10 10 10 10 10 10 10 10 6 2 6 10 8 2 10 2Ryegrass 10 10 9 10 6 10 10 8 0 0 7 10 5 0 9 8Sugar beet 10 10 10 10 10 10 10 10 6 9 5 10 6 2 10 9Sunflower 10 10 10 10 10 10 10 10 3 0 10 10 10 9 0 10Wheat (Spring) 7 9 7 5 2 10 7 3 10 6 9 10 6 0 9 5Wheat (Winter) 7 9 7 4 2 10 8 3 10 7 9 10 6 0 9 4Wild buckwheat 10 10 10 10 8 10 10 10 5 7 6 10 2 0 10 8Wild mustard 10 10 10 10 10 10 10 10 7 7 10 10 10 6 10 9Wild oat (1) 9 10 10 4 2 10 9 8 8 6 10 10 4 0 6 6Wild oat (2) 9 10 10 5 3 10 9 8 9 6 10 10 4 2 6 5Wild radish 10 10 10 10 10 10 10 10 4 5 7 10 10 3 10 8Winter Barley 10 10 9 10 4 10 10 10 10 9 9 10 8 3 8 5__________________________________________________________________________ COMPOUNDRate (64 g/ha) 36 59 60 83 89 107 108 214 229 230 232 244 252 269 288 289__________________________________________________________________________POSTEMERGENCEBlackgrass (1) -- 9 6 10 9 10 6 8 5 7 10 10 10 2 10 10Blackgrass (2) -- 9 5 9 7 10 5 8 6 8 10 10 10 2 10 10Chickweed -- 10 10 10 4 10 10 10 5 4 8 10 3 0 10 10Downy brome -- 6 5 3 2 5 3 10 6 8 10 10 10 4 10 10Field violet -- 10 7 6 0 10 10 8 4 7 6 10 6 0 8 5Galium (1) -- 10 9 8 7 10 10 10 8 8 10 10 9 2 10 8Galium (2) -- 10 9 9 6 10 10 10 7 7 10 10 9 2 10 8Green foxtail -- 8 5 7 3 10 3 7 4 7 3 10 10 0 10 10Kochia -- 10 10 10 0 10 10 9 2 4 3 5 2 4 10 10Lambsquarters -- 7 3 6 2 8 2 4 6 8 2 5 3 0 8 7Persn Speedwell -- 10 2 0 0 10 0 2 0 0 0 0 2 0 4 2Rape -- 10 10 10 10 10 10 10 10 10 10 10 10 4 10 5Ryegrass -- 10 7 6 2 10 10 8 3 0 10 10 4 2 8 8Sugar beet -- 10 10 10 7 10 10 10 5 6 7 10 4 0 10 9Sunflower -- 10 10 10 10 10 10 10 10 10 10 10 10 3 10 10Wheat (Spring) -- 4 2 5 2 6 2 4 6 5 9 10 7 0 9 10Wheat (Winter) -- 4 2 4 2 5 2 4 7 6 10 10 7 0 9 10Wild buckwheat -- 10 10 6 2 10 10 10 4 6 2 10 0 9 10 5Wild mustard -- 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10Wild oat (1) -- 8 6 2 0 10 5 9 10 10 10 10 8 2 10 10Wild oat (2) -- 8 6 2 0 10 5 10 10 10 10 10 6 0 10 10Wild radish -- 10 10 10 10 10 10 10 7 7 10 10 10 7 10 10Winter Barley -- 7 5 6 2 7 5 8 9 9 9 10 6 3 9 10__________________________________________________________________________ COMPOUNDRate (64 g/ha) 36 59 60 83 89 107 108 214 229 230 232 244 252 269 288 289__________________________________________________________________________PREEMERGENCEBlackgrass (1) 10 10 7 8 6 9 7 7 3 4 5 10 8 0 7 8Blackgrass (2) 10 10 9 9 6 9 6 7 5 4 4 10 8 0 6 8Chickweed 10 10 10 10 10 10 10 10 6 4 5 10 8 2 10 9Downy brome 10 9 7 4 0 8 6 10 9 6 9 10 7 0 6 7Field violet 10 10 10 10 8 10 10 10 5 7 3 10 9 0 10 6Galium (1) 10 10 10 10 10 10 10 10 9 7 4 10 6 0 10 7Galium (2) -- 10 10 10 10 10 10 10 -- 7 4 10 7 0 10 8Green foxtail 10 10 8 10 5 10 7 9 4 2 6 10 6 0 6 8Kochia 7 10 10 10 5 10 10 8 2 0 3 9 2 0 10 6Lambsquarters 10 10 10 10 10 10 10 10 4 4 0 10 9 0 10 3Persn Speedwell 4 10 9 9 6 10 10 7 4 2 3 6 8 0 10 7Rape 10 10 10 10 10 10 10 10 3 0 3 10 6 0 10 0Ryegrass 10 10 8 8 3 10 9 6 0 0 5 9 2 0 7 5Sugar beet 10 10 10 10 10 10 10 10 4 7 3 10 4 0 10 8Sunflower 10 10 10 10 10 10 10 10 0 0 8 10 5 0 10 7Wheat (Spring) 5 8 6 3 0 8 6 3 9 3 8 8 4 0 7 3Wheat (Winter) 5 7 5 3 0 8 6 2 10 4 7 8 5 0 8 2Wild buckwheat 10 10 10 10 6 10 10 10 2 5 4 10 0 0 10 6Wild mustard 8 10 10 10 10 10 10 10 3 3 8 10 10 3 10 7Wild oat (1) 6 10 9 3 0 10 8 6 7 4 7 10 2 0 5 5Wild oat (2) 7 10 9 3 0 10 8 6 6 4 8 10 2 0 5 4Wild radish 10 10 10 10 10 10 10 8 3 2 4 10 8 0 10 5Winter Barley 9 10 8 8 2 10 10 8 9 6 6 10 5 2 7 4__________________________________________________________________________ COMPOUNDRate (32 g/ha) 36 59 60 83 89 107 108 214 229 230 232 244 252 269 288 289__________________________________________________________________________POSTEMERGENCEBlackgrass (1) -- 8 5 8 6 8 4 6 4 6 9 10 9 0 9 10Blackgrass (2) -- 7 4 7 4 8 4 7 4 6 10 10 8 0 8 10Chickweed -- 10 10 10 2 10 10 10 4 2 4 10 2 0 8 10Downy brome -- 5 4 3 0 3 2 8 4 6 9 10 8 2 10 10Field violet -- 10 4 4 0 10 8 5 2 5 5 10 4 0 6 2Galium (1) -- 10 8 7 4 10 10 9 7 6 9 10 7 0 9 7Galium (2) -- 10 8 8 3 10 10 10 6 6 9 10 8 0 8 6Green foxtail -- 7 3 6 0 10 0 5 3 6 2 10 8 0 10 10Kochia -- 10 9 8 0 10 8 7 0 2 0 3 0 2 10 10Lambsquarters -- 6 0 5 0 6 0 2 4 6 0 2 2 0 6 5Persn Speedwell -- 10 0 0 0 9 0 0 0 0 0 0 0 0 2 0Rape -- 10 10 10 10 10 10 10 8 9 10 10 9 2 10 3Ryegrass -- 10 6 5 0 10 9 6 2 0 8 10 2 0 7 5Sugar beet -- 10 10 10 5 10 10 10 3 3 4 10 3 0 9 7Sunflower -- 10 10 10 10 10 10 10 10 10 10 10 10 0 10 10Wheat (Spring) -- 3 0 3 0 4 0 2 5 4 8 10 4 0 8 10Wheat (Winter) -- 4 0 3 0 3 0 2 6 3 8 10 4 0 8 10Wild buckwheat -- 10 8 3 0 10 10 10 2 3 0 10 0 7 8 3Wild mustard -- 10 10 10 10 10 10 10 10 10 10 10 10 7 10 10Wild oat (1) -- 7 5 0 0 8 4 8 8 8 10 10 4 0 10 10Wild oat (2) -- 7 5 0 0 7 4 9 8 8 10 10 3 0 9 10Wild radish -- 10 10 10 10 10 8 10 4 5 10 10 10 5 10 8Winter Barley -- 6 2 5 0 5 3 6 8 7 7 9 3 2 7 10__________________________________________________________________________ COMPOUNDRate (32 g/ha) 36 59 60 83 89 107 108 214 229 230 232 244 252 269 288 289__________________________________________________________________________PREEMERGENCEBlackgrass (1) 9 9 6 7 3 8 5 5 0 3 2 10 6 0 4 6Blackgrass (2) 9 9 7 7 4 8 5 6 2 2 2 9 6 0 3 5Chickweed 10 10 10 10 8 10 10 9 3 2 2 10 5 0 10 8Downy brome 10 8 6 3 0 7 4 8 7 4 7 10 4 0 4 4Field violet 10 10 10 10 6 10 10 10 2 3 2 10 6 0 10 3Galium (1) 9 10 10 10 10 10 10 10 5 5 3 10 4 0 9 5Galium (2) -- 10 10 10 10 10 10 10 -- 3 2 10 4 0 8 4Green foxtail 9 9 7 9 2 9 6 7 2 0 4 10 5 0 4 7Kochia 4 10 9 8 2 10 9 5 0 0 2 7 0 0 10 5Lambsquarters 10 10 10 10 7 10 10 9 2 2 0 10 7 0 10 2Persn Speedwell 2 10 8 6 5 10 8 5 2 0 0 4 5 0 10 5Rape 10 10 10 10 10 10 10 10 0 0 0 10 4 0 10 0Ryegrass 8 10 7 6 2 10 7 4 0 0 2 7 0 0 5 3Sugar beet 10 10 10 10 9 10 10 10 2 4 2 10 3 0 10 6Sunflower 10 10 10 10 10 10 10 9 0 0 4 10 3 0 10 4Wheat (Spring) 3 6 5 2 0 6 4 2 8 2 4 5 3 0 4 0Wheat (Winter) 3 6 4 2 0 7 4 2 8 2 4 6 3 0 6 0Wild buckwheat 7 10 10 10 4 10 10 10 0 2 2 8 0 0 8 4Wild mustard 7 10 10 10 10 10 10 10 0 0 4 10 8 0 10 5Wild oat (1) 3 10 8 2 0 10 7 3 4 2 4 8 0 0 3 3Wild oat (2) 3 10 8 0 0 10 7 4 5 2 5 8 0 0 3 2Wild radish 7 10 10 10 10 10 10 7 2 0 2 10 6 0 10 3Winter Barley 4 9 7 7 0 10 10 6 8 3 3 8 3 0 5 2__________________________________________________________________________ COMPOUNDRate (16 g/ha) 36 59 60 83 89 107 108 214 229 230 232 244 252 269 288 289__________________________________________________________________________POSTEMERGENCEBlackgrass (1) 5 7 3 6 3 7 3 4 3 4 7 9 7 0 7 9Blackgrass (2) 4 6 2 5 2 6 2 3 2 3 8 9 5 0 6 8Chickweed 5 10 10 8 0 10 10 10 2 0 2 10 0 0 6 8Downy brome 10 3 3 0 0 2 0 6 3 5 7 10 5 0 8 10Field violet 5 9 2 2 0 10 6 3 0 2 3 8 2 0 3 0Galium (1) 7 9 7 4 2 10 10 7 6 3 7 8 6 0 7 5Galium (2) -- 10 6 5 2 10 10 8 5 3 6 8 7 0 7 4Green foxtail 10 6 0 4 0 7 0 3 2 4 0 10 6 0 8 8Kochia 4 10 6 6 0 10 7 6 0 0 0 2 0 0 9 9Lambsquarters 5 4 0 2 0 4 0 0 2 4 0 0 0 0 4 4Persn Speedwell 0 10 0 0 0 6 0 0 0 0 0 0 0 0 0 0Rape 10 10 10 9 10 8 10 10 6 7 10 10 7 0 10 2Ryegrass 10 9 3 3 0 10 7 4 0 0 6 8 0 0 5 3Sugar beet 10 10 10 10 4 10 10 10 2 0 2 10 0 0 8 6Sunflower 10 10 10 10 10 10 10 10 10 10 10 10 10 0 9 10Wheat (Spring) 6 2 0 2 0 2 0 0 3 2 6 7 2 0 7 8Wheat (Winter) 4 3 0 2 0 2 0 0 3 2 6 8 2 0 6 8Wild buckwheat 2 10 5 2 0 10 8 10 0 0 0 8 0 4 6 0Wild mustard 10 10 10 10 10 10 10 10 9 10 10 10 10 6 10 10Wild oat (1) 10 5 3 0 0 5 2 6 7 6 10 10 2 0 9 9Wild oat (2) 9 5 4 0 0 5 2 7 6 6 10 10 2 0 8 10Wild radish 9 10 10 10 10 8 5 10 3 4 10 10 10 2 10 5Winter Barley 4 5 0 3 0 3 2 3 6 5 6 6 2 0 5 9__________________________________________________________________________ COMPOUNDRate (16 g/ha) 36 59 60 83 89 107 108 214 229 230 232 244 252 269 288 289__________________________________________________________________________PREEMERGENCEBlackgrass (1) 6 8 5 5 2 6 3 4 0 0 0 8 5 0 2 2Blackgrass (2) 8 8 6 6 2 6 3 4 0 0 0 7 4 0 2 2Chickweed 10 10 10 9 6 10 10 8 0 0 0 10 3 0 10 6Downy brome 8 7 5 2 0 5 3 6 3 2 5 9 2 0 2 2Field violet 8 10 10 10 5 10 10 10 0 0 0 8 3 0 10 0Galium (1) 7 10 10 9 8 10 8 8 2 2 0 9 2 0 4 3Galium (2) -- 10 10 10 8 10 10 9 -- 0 0 9 2 0 5 3Green foxtail 7 8 5 7 0 7 3 4 0 0 2 9 3 0 2 5Kochia 2 10 8 5 0 8 7 2 0 0 0 3 0 0 7 3Lambsquarters 10 10 9 10 4 10 9 7 0 0 0 8 4 0 8 0Persn Speedwell 0 10 7 4 3 10 6 4 0 0 0 2 3 0 10 2Rape 8 10 10 10 8 10 9 10 0 0 0 9 2 0 8 0Ryegrass 4 9 5 4 0 10 5 3 0 0 0 6 0 0 2 0Sugar beet 9 10 10 10 5 10 10 10 0 2 0 10 2 0 9 4Sunflower 8 10 10 10 9 10 10 6 0 0 2 10 0 0 9 2Wheat (Spring) 0 4 3 0 0 5 3 0 5 0 2 2 2 0 2 0Wheat (Winter) 0 4 3 0 0 4 3 0 6 0 2 3 2 0 3 0Wild buckwheat 5 10 9 8 3 10 9 10 0 0 0 4 0 0 7 2Wild mustard 5 10 10 10 10 10 10 10 0 0 2 10 6 0 10 3Wild oat (1) 0 8 6 0 0 10 6 2 2 0 3 5 0 0 2 0Wild oat (2) 0 9 6 0 0 10 6 2 2 0 3 4 0 0 2 0Wild radish 6 10 10 10 10 10 9 5 0 0 0 7 4 0 10 0Winter Barley 2 8 5 4 0 9 9 3 4 2 2 5 2 0 3 0__________________________________________________________________________ COMPOUNDRate (8 g/ha) 36 59 60 83 89 107 108 214 229 230 232 244 252 269 288 289__________________________________________________________________________POSTEMERGENCEBlackgrass (1) 3 4 2 3 2 3 0 2 2 2 4 7 4 0 6 8Blackgrass (2) 2 4 0 2 0 3 0 2 0 2 5 7 3 0 4 6Chickweed 3 10 10 6 0 10 9 10 0 0 0 10 0 0 4 6Downy brome 9 2 2 0 0 0 0 5 2 3 5 9 2 0 7 9Field violet 3 8 0 0 0 8 3 0 0 0 2 6 0 0 2 0Galium (1) 4 8 4 2 0 10 10 5 3 0 3 4 3 0 5 2Galium (2) -- 7 4 2 0 10 9 5 4 0 3 5 4 0 4 2Green foxtail 9 4 0 3 0 3 0 2 0 2 0 8 4 0 7 6Kochia 2 10 3 4 0 10 5 4 0 0 0 0 0 0 7 7Lambsquarters 4 2 0 0 0 2 0 0 0 2 0 0 0 0 2 2Persn Speedwell 0 10 0 0 0 3 0 0 0 0 0 0 0 0 0 0Rape 10 10 9 7 9 6 8 10 3 3 9 10 4 0 10 0Ryegrass 9 7 2 2 0 10 5 2 0 0 4 5 0 0 3 2Sugar beet 10 10 9 10 2 10 10 10 0 0 0 10 0 0 7 5Sunflower 10 10 10 10 10 10 10 10 9 8 10 10 10 0 8 10Wheat (Spring) 3 0 0 0 0 0 0 0 0 0 3 5 0 0 5 7Wheat (Winter) 2 0 0 0 0 0 0 0 0 0 4 5 0 0 4 7Wild buckwheat 0 8 3 0 0 9 5 8 0 0 0 7 0 2 5 0Wild mustard 8 10 10 10 10 10 9 10 7 9 8 10 10 4 10 10Wild oat (1) 7 4 2 0 0 4 0 4 4 5 9 10 0 0 8 8Wild oat (2) 7 3 2 0 0 3 0 5 5 4 8 10 0 0 6 7Wild radish 6 10 9 10 9 7 3 10 0 3 8 10 10 0 10 5Winter Barley 2 4 0 0 0 2 0 2 4 2 3 4 0 0 4 6__________________________________________________________________________ COMPOUNDRate (8 g/ha) 36 59 60 83 89 107 108 214 229 230 232 244 252 269 288 289__________________________________________________________________________PREEMERGENCEBlackgrass (1) 4 7 4 3 0 3 0 2 0 0 0 6 2 0 0 0Blackgrass (2) 4 7 5 4 0 3 0 2 0 0 0 5 2 0 0 0Chickweed 9 10 10 7 3 10 10 6 0 0 0 10 2 0 8 4Downy brome 5 6 2 0 0 4 2 3 0 0 3 7 0 0 0 0Field violet 6 10 10 8 2 10 10 9 0 0 0 6 0 0 8 0Galium (1) 5 10 10 8 5 9 5 6 0 0 0 6 0 0 2 2Galium (2) -- 10 10 8 4 10 7 7 -- 0 0 7 0 0 3 0Green foxtail 5 7 2 4 0 5 0 2 0 0 0 6 2 0 0 3Kochia 0 9 7 3 0 6 5 0 0 0 0 0 0 0 5 2Lambsquarters 7 10 8 9 2 9 6 4 0 0 0 7 2 0 7 0Persn Speedwell 0 10 6 2 2 10 3 3 0 0 0 0 2 0 8 0Rape 6 10 10 10 7 10 6 10 0 0 0 5 0 0 6 0Ryegrass 2 8 3 3 0 8 3 2 0 0 0 4 0 0 0 0Sugar beet 6 10 10 9 2 10 9 9 0 0 0 10 0 0 7 3Sunflower 4 10 10 10 3 10 10 5 0 0 0 10 0 0 5 0Wheat (Spring) 0 3 2 0 0 3 2 0 2 0 0 0 0 0 0 0Wheat (Winter) 0 3 2 0 0 3 2 0 3 0 0 0 0 0 0 0Wild buckwheat 3 10 8 6 0 9 7 8 0 0 0 2 0 0 5 0Wild mustard 2 10 10 10 10 10 10 9 0 0 0 9 3 0 10 2Wild oat (1) 0 7 4 0 0 8 4 0 0 0 2 2 0 0 0 0Wild oat (2) 0 7 5 0 0 8 5 0 0 0 2 2 0 0 0 0Wild radish 4 10 9 10 10 9 6 4 0 0 0 4 2 0 8 0Winter Barley 0 7 2 3 0 7 7 2 2 0 0 3 0 0 0 0__________________________________________________________________________ COMPOUNDRate (4 g/ha) 36 59 60 83 89 107 108 214 229 230 232 244 252 269 288 289__________________________________________________________________________POSTEMERGENCEBlackgrass (1) 0 2 0 2 0 0 0 0 0 0 2 5 2 0 4 6Blackgrass (2) 0 2 0 0 0 0 0 0 0 0 3 6 2 0 2 4Chickweed 0 10 8 3 0 7 5 7 0 0 0 9 0 0 2 4Downy brome 7 0 0 0 0 0 0 3 0 0 4 7 0 0 5 7Field violet 2 5 0 0 0 5 2 0 0 0 0 4 0 0 0 0Galium (1) 2 4 2 0 0 7 7 2 2 0 0 2 0 0 2 0Galium (2) -- 4 2 0 0 10 6 2 2 0 0 3 2 0 3 0Green foxtail 3 2 0 2 0 0 0 0 0 0 0 4 2 0 6 3Kochia 0 8 2 2 0 6 3 3 0 0 0 0 0 0 5 5Lambsquarters 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0Persn Speedwell 0 8 0 0 0 2 0 0 0 0 0 0 0 0 0 0Rape 9 10 4 5 8 5 7 6 0 0 7 10 3 0 10 0Ryegrass 5 5 0 0 0 10 3 0 0 0 2 3 0 0 2 0Sugar beet 7 10 6 9 0 10 10 7 0 0 0 10 0 0 6 2Sunflower 10 10 10 10 7 10 9 10 7 7 10 10 9 0 6 7Wheat (Spring) 0 0 0 0 0 0 0 0 0 0 2 3 0 0 4 5Wheat (Winter) 0 0 0 0 0 0 0 0 0 0 2 3 0 0 3 5Wild buckwheat 0 6 0 0 0 5 3 6 0 0 0 5 0 0 4 0Wild mustard 6 10 10 10 10 10 7 9 3 8 6 8 8 2 10 8Wild oat (1) 4 2 0 0 0 2 0 2 2 3 6 8 0 0 7 4Wild oat (2) 4 2 0 0 0 2 0 2 3 2 6 9 0 0 5 3Wild radish 5 10 7 10 7 5 2 7 0 0 5 10 8 0 9 4Winter Barley 0 2 0 0 0 0 0 0 2 0 0 2 0 0 2 5__________________________________________________________________________ COMPOUNDRate (4 g/ha) 36 59 60 83 89 107 108 214 229 230 232 244 252 269 288 289__________________________________________________________________________PREEMERGENCEBlackgrass (1) 2 6 2 2 0 0 0 0 0 0 0 3 0 0 0 0Blackgrass (2) 2 6 3 3 0 0 0 0 0 0 0 3 0 0 0 0Chickweed 6 9 8 5 2 10 9 3 0 0 0 8 0 0 6 2Downy brome 2 5 0 0 0 2 0 2 0 0 0 3 0 0 0 0Field violet 3 9 9 6 0 8 8 7 0 0 0 3 0 0 7 0Galium (1) 2 9 8 6 2 6 3 4 0 0 0 4 0 0 0 0Galium (2) -- 9 8 6 3 9 5 4 -- 0 0 4 0 0 2 0Green foxtail 2 6 0 2 0 2 0 0 0 0 0 5 0 0 0 0Kochia 0 8 5 0 0 4 2 0 0 0 0 0 0 0 2 0Lambsquarters 4 8 7 6 0 6 5 3 0 0 0 3 0 0 5 0Persn Speedwell 0 10 5 0 0 10 2 2 0 0 0 0 0 0 6 0Rape 4 10 10 8 4 8 5 8 0 0 0 3 0 0 4 0Ryegrass 0 7 2 2 0 6 2 0 0 0 0 2 0 0Sugar beet 4 10 10 8 0 10 8 8 0 0 0 8 0 0 6 0Sunflower 2 10 10 9 0 10 10 3 0 0 0 7 0 0 2 0Wheat (Spring) 0 2 0 0 0 2 0 0 0 0 0 0 0 0 0 0Wheat (Winter) 0 2 0 0 0 2 0 0 0 0 0 0 0 0 0 0Wild buckwheat 0 8 7 4 0 8 4 5 0 0 0 0 0 0 4 0Wild mustard 0 10 10 10 7 10 9 7 0 0 0 8 0 0 10 0Wild oat (1) 0 6 2 0 0 4 2 0 0 0 0 0 0 0 0 0Wild oat (2) 0 5 2 0 0 4 3 0 0 0 0 0 0 0 0 0Wild radish 2 9 7 10 9 8 4 2 0 0 0 2 0 0 6 0Winter Barley 0 6 0 0 0 5 5 0 0 0 0 2 0 0 0 0__________________________________________________________________________ COMPOUNDRate (2 g/ha) 36 107 108 232 252 289__________________________________________________________________________POSTEMERGENCEBlackgrass (1) 0 0 0 0 0 0Blackgrass (2) 0 0 0 0 0 0Chickweed 0 3 2 0 0 2Downy brome 3 0 0 2 0 3Field violet 0 3 0 0 0 0Galium (1) 0 3 3 0 0 0Galium (2) -- 3 3 0 0 0Green foxtail 4 0 0 0 0 0Kochia 0 3 0 0 0 2Lambsquarters 0 0 0 0 0 0Persn Speedwell 0 0 0 0 0 0Rape 5 3 5 5 0 0Ryegrass 2 7 0 0 0 0Sugar beet 3 9 9 0 0 0Sunflower 9 10 5 10 5 4Wheat (Spring) 0 0 0 0 0 2Wheat (Winter) 0 0 0 0 0 2Wild buckwheat 0 2 2 0 0 0Wild mustard 4 10 3 4 5 7Wild oat (1) 2 0 0 2 0 2Wild oat (2) 3 0 0 3 0 2Wild radish 3 2 0 2 5 0Winter Barley 0 0 0 0 0 3__________________________________________________________________________ COMPOUNDRate (2 g/ha) 36 107 108 232 252 289__________________________________________________________________________PREEMERGENCEBlackgrass (1) -- 0 0 0 0 0Blackgrass (2) -- 0 0 0 0 0Chickweed -- 8 7 0 0 0Downy brome -- 0 0 0 0 0Field violet -- 6 5 0 0 0Galium (1) -- 4 0 0 0 0Galium (2) -- 5 2 0 0 0Green foxtail -- 0 0 0 0 0Kochia -- 2 0 0 0 0Lambsquarters -- 5 3 0 0 0Persn Speedwell -- 8 0 0 0 0Rape -- 5 2 0 0 0Ryegrass -- 3 0 0 0 0Sugar beet -- 9 5 0 0 0Sunflower -- 9 9 0 0 0Wheat (Spring) -- 0 0 0 0 0Wheat (Winter) -- 0 0 0 0 0Wild buckwheat -- 6 3 0 0 0Wild mustard -- 9 7 0 0 0Wild oat (1) -- 2 0 0 0 0Wild oat (2) -- 2 0 0 0 0Wild radish -- 6 2 0 0 0Winter Barley -- 3 2 0 0 0__________________________________________________________________________

Number	Name	Date
4368067	Budzinski et al.	Jan 1983
4401816	Levitt	Aug 1983
4518776	Meyer et al.	May 1985
4549898	Bohner et al.	Oct 1985
4639264	Topfl	Jan 1987
4685961	Topfl et al.	Aug 1987
4737184	Pasteris	Apr 1988
4756742	Thompson	Jul 1988
5356862	Zimmerman	Oct 1994

Number	Date	Country
0039239	Nov 1981	EPX
0097122	Dec 1983	EPX
0101670	Feb 1984	EPX
00126711	Nov 1984	EPX
0161211	Nov 1985	EPX

Herbicidal pyrrolesulfonylureas

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Abstract

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CROSS-REFERENCE TO RELATED APPLICATION

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