CA2079589A1

CA2079589A1 - Crop-selective herbicidal sulfonamides

Info

Publication number: CA2079589A1
Application number: CA 2079589
Authority: CA
Inventors: Marcus P. Moon
Original assignee: Individual
Current assignee: EIDP Inc
Priority date: 1990-04-02
Filing date: 1991-02-26
Publication date: 1991-10-03
Also published as: JP2799246B2; EP0523067A1; WO1991015478A1; BR9106301A; JPH05505796A

Abstract

This invention relates to novel sulfonamides and their use as crop selective herbicides. Compounds of the instant invention have demonstrated excellent control of weeds coupled with corn safety.

Description

WO91/1~78 PCT/US91/01075 2~ J.~ 9 ~E
CROP-SELECTIVE HER~ICID~L SULFONAMIDES
C~QSS=EEE~EXÇE TO B~L~ED Ap~kI~AlIQ~
This is a continuation-in-part of application Serial No. 07/503,182, filed April 4, l990.
BACKGROUND OF THE INVEN~ION
This in~ention relates to novel sulfonamides and their use as crop selective herbicides.
Compounds of the instant invention have demonstrated e~cellent control of weeds coupled with corn safety.
EP-A-120,814 discloses herbicidal sulfonylureas of the formula lS

R~

wheroin:
A is Cl-C6 haloalkyl;
Rl i8 H, halo9en, NO2, CN, Cl-C4 alkyl, Cl-C4 haloalkyl, Cl-C4 alkosy, Cl-C4 alkylthio, Cl-C4 alkylsulfinyl, Cl-C4 alkylsulfonyl, COR6, NR7RB, CoNR9Rl0 or SO2NRllRl2; anD
R6 is Cl-C4 alko~y, Cl-C4 haloalko~y, Cl-C4 alkylthio, C2-C6 alko~yalko~y, hydrogen, Cl-C4 alkyl or Cl-C4 haloalkyl.
Although this reference broadly embraces compounds of the instant invention, it does not teach or suggest these particular compounds or their herbicidal utility.

WO91/1~78 PCT/US91/01075 7~.~J9 Additionally, a need still e~ists for herbicides because of world-wide food ~hortages. In S addition, herbicides which are selective to important crops such as corn are particularly necessary.
According to the instant invention, such compounds have been found.
SUMMARY OF THE INVENTION
More specifically, this invention comprises novel compounds of Formula I, agriculturally suitable compositions containing them, and their method-of-use as preemergence and/or postemergence herbicides or plant growth regulants:

C(O)A o X
~(Ol~NHCN~

wh-rein:
A i~ ORl or N(CH3)2;
Rl ~8 Cl-C3 ~lkyl, CH2CH.CH2, CH2C--CH, CH2CH2Cl or CH2CH2OCH3;
R2 ~8 CH2F, CHF2, CHFCH3 or CH2CN;
~ is CH3 or OCH3; and Y is H, Cl, CH3, C2Hs, OCH3 or OCF2H:
and their agriculturally suitable salts: provided that when Y is Cl, then X is OCH3.
In the above definitions, the term ~alkyl~
denotes straight chain or branched alkyl, e.g.

. ' ~', ' ' .' , . ` . ' ' ,' ~ ~, , ' ,, . ~ -. . : : - , ' - , :

;. WO91/1~78 PCTtUS91/01075 3 ~ 2~iJ~9 methyl, ethyl, n-propyl or isopropyl. The total number of carbon atoms in a ~ubstituent group is S indicate~ by the Ci-Cj prefis where i and ; ~re numbers 1 to 3. For esample, Cl-C3 alkyl would designate methyl through propyl (both n-ProPyl and isopropyl).
Preferred for reasons of increased ease of synthesis and/or greater herbicidal efficacy and/or crop safety are:
1. Compounds of Formula I wherein A is ORl; snd Rl is CH3, CH2CH3 or CH(CH3)2.
2. Compounds of Preferred 1 where when one of ~ an~ Y is CH3, then the other of ~ and Y is other than OCH3.
Specifically preferred for reason of greatest safety to corn (maize) is:
Methyl 3-(cyanomethyl)-2-tt[1(4,6-dimethyl-2-pyrimidinyl)amino]carbonyl]-amino]sulfonyl]benzoate (Formula I:
A is ORl, Rl i8 CH3, R2 is CH2CN, X an~ Y
are CH3.
~pecifically Proferred for reason of greatest ~afoty to corn, wheat and barley are:
; M-thyl 2-[ttt~4-chloro-6-metho~y-2-pyr~m~dinyl)am~no]carbonyl]amino]~ulfonyl]-3-~cyanomethyl)benzoate (Formula 1: A ~s ORl, Rl ~s CH3, R2 is CH2CN, X is OCH3, Y is Cl);
Methyl 3-(cyanomethyl)-2-[t[[[(4-(difluorometho~y)-6-metho~y-2-pyr~mldinyl]-amino]carbonyl]amino]sulfonyl]benzo~te ~Formula I: A is ORl, Rl is CH3, R2 ~s CH2CN, X is OCH3, Y is OCF2H);
Methyl 3-~difluoromethyl)-2-tttt~4-metho~y-2-pyrimidinyl)amino]carbonyl]amino]sulfonyll-, . .
- , , . - , .
'' , ~ ' ' ": ' ' , WO91/1~78 PCT/US91/01075 5'9 4 benzoate (Formula I: A is ORl, Rl is CH3, R2 is CHF2 X is OCH3, Y is H);
Methyl 3-(fluoromethyl)-2-t~t[(4-methosy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl)-benzoate (Formula I: A is ORl, Rl is CH3, R2 is CH2F, X is OCH3, Y is H).
Specifically preferred for reason of greatest safety to wheat and barley is:
Methyl 2-[[[[(4,6-dimetho~y-2-pyrimidinyl)-amino]carbonyl]amino]sulfonyl]-3-(fluoromethyl)benzoate (Formula I: A is ORl, Rl is CH3, R2 is CH2F, X and Y are OCH3).
~pecifically preferred for reason of greatest safety to corn, wheat, barley and rice is:
Ethyl 2-[~[(4-chloro-6-metho~y-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]-3-(fluoromethyl)benzoate (Formula I:
A is ORl, Rl is CH2CH3, R2 is CH2F, X is OCH3, Y is Cl).
This invention ~lso comprises novel compounds, such as the sulfonyl benzo~tes of Formula II, useful ~8 ~ntermedi~te~ for prepar~tion of the compounds of Formula 1:

C~O)A
~O;~Z~ ' Il ... . . . . . . .

WO 91/15478 PCl/US91/01075 ~ ~9 wherein:
A is ORl or N(CH3)2;
Rl is Cl-C3 ~lkyl, CH2CH-CH2, CH2C_CH, CH2CH2Cl o~ CH2CH20CH3;
R2 is CH2F, CHF2, CHFCH3 or CH2CN; and zl is Cl or NHSiR3R4R5;
R3 is Cl-C4 alkyl:
R4 is Cl-C4 ~lkyl; a~d R5 is Cl-C4 alkyl.
Preferred for reason of increased herbicidal activity of final products of Formula I, are intermediates of Formula II wherein A is ORl and is Cl-C2 alkyl.
Preferred for reason of increased ease of synthesis are intermediates of the above preferred wherein R3 ~nd R4 are CH3 ~nd R5 is C(CH3)3.
DETAILE~ DESCRI~TION OF THE INVEN~ION

~ 1 ) ,~;y,~ T S
The compounds of Formula (l), which corresponds to Formula I, can be prepared by one or more of the methods described below. The proper choice of r-action sequences for a given compound will be known to one skilled in the art.

.

.' . . ~ . :. . ~, . '- , . '`: . , - :, : - - ' ': : ' - .:
.. . .... . . . . . . .
, , .
. ' - .
.

. : ~ . . ..

WO9l/1~78 PCT/US91/01075 ,~, ~

As ~hown in Equation 1, many of the compounds of Formula (1) are prepared by reacting ~ silyl S ~ulfon~mide of Formula (2) with a pyrimidine c~rbam~te of Formula (3). R3, R4, ~nd R5 are independently Cl to C4 alkyl.
E~tion ~D~N~ J~ ~CNHJ~ (1) (2) (~) The reaction is carried out at 0C to 50C in a solvent such as acetonitrile, diosane, or tetrahydrofuran; in the presence of a fluoride ion source such as cesium fluoride, or tetrabutylammonium fluoride for 0.1 to 2 hours. ~ catalytic amount of base, ~uch as 1,3-diazabicyclo[5.4.0]undec-7-ene (D~U), increa~es the reaction rate.
Alternatively, some of the sulfonamides of Formula ~4) can be prepared and reacted with pyrimidine carbamates of Formula (3) to ~ive ~0 compounds of Formula ~1) as shown in Equation 2. The reaction i8 carried out at 0C to 50C in a solvent, such as acqtonitrile, diosane, or tetrahydrofuran, in the presence of a non-nucleophilic base, such as D~U
for 0.2 to 2 hours. U.S. Patent 4,604,131 discloses details for ~imilar reactions and is herein ~ncorporated by reference.

..
- ~
. . . . . . . - , . :
: . . . -- -,, , . .' - '' - :
.. . .
: . -... . . . . . .

WOgl/l~78 PCT/US91/01075 ~, ~
7 ~ rf `~

Equation.

~2NH~ ~NH ~ ~ ( 1 ) (4) (3) Sulfonyl chlorides of Formula (5) may be reacted with cyanate anion in the presence of pyrimidine amine~ of Formula (6) to give compounds of ~ormula (1) as shown in Equation 3.
Equation 3 I

ucO ~

~5) (~) The reaction is carrie~ out by mising one ~qui~alent of sulfonyl chloride.(5), pyrimidine amine (6), a metal cyanate, such as potassium cyanate, and a catalytic amount of an amine base, such as AliquatO
336 (Tricaprylymethylammonium chloride), in a solvent such as acetonitrile for 0.2 to 10 days.

. ~ . . . - .. v -.
.. . ~ ,, , " .~
, .-. - ',.'. ' . - ~ - , . . .
.. . ~ ~. . . . -. .

- - - . : . -. -, - ..

i WO91/1~78 PCT/US91/01075 i~ ~, Z~ g 8 Alternatively, one can use a tetraalkylammonium cyanate, su~h as tetraethylammonium cyanate, to effect this reaction by the method described in U.S.
Patent 4,604,131 herein incorporated by reference.
Silyl sulfonamides of Formula (2) are prepared by reacting sulfonyl chlorides of Formula (5) with a trialkylsilyl amine of Formula (7), su~h as t-butyldimethylsilyl amine, AS shown in Equation 4.
Equation 4 (~ ~ H NSlR~R~R~ ~ (2) -r OlCl ~ (7 ,' The reaction is carried out at ODC to 30C in a solvent, ~uch a8 dichloromethane, in the presence of 1 to 2 oqui~alents of the amine and 1 equi~alent of a b~carbonato. J. R. ~ow~er et. al. describe methods to prepare ~lyl amines of Formula ~7) in Inorganic Chemistry 17, la82 ~197~).
- 30 The ~ulfonyl chlorides of Formula (5) and the silyl ~ulfonamides of Formula (2) correspond to the intermediates of Formula II.
Sulfonyl chlorides of Formula (5) can be reacted with no more than 2 egui~alents of ammonia or, alternatively, 1 equivalent of ammonia and 1 eguivalent of a base to gi~e sulfonamides of Formula (4) as outlined in Equation 5.

.- - -.... .: ', . . ,' . :. ~.
.
.
. , . ' . . . ,' ' - ' ,' ,, ' .

~ WOgl/1~78 PCT/US91/01075 ~.j, h~ 2~ r b J9 ,, ( 5 ) ~ NH3 Bl~ ~ [~( O) A

0 ~Ç 2NH2 (4) Sulfonamides of Formula (4) tend to be unstable and can be difficult to isolate.
Sulfonyl chlorides of Formula (5) are prepared by the methods shown in Equations 6 and 7.
Sulfur-containing compounds of Formula (8) are osidized with chlorine as shown in Equation 6. R6 is H, alkyl, benzyl or carbamoyl.
~quation 6 ~C(O)A
~ Cl~ O

~

(~) The reaction of Equation 6 is carried out by contacting compounds of Formula (8) in a solvent, such as acetic acid or propionic acid, with 8t least '.` . ,, : :

WO91/1~78 PCT/~S91/01075 ~, ~

3.0 equivalents of chlorine in the presence of at least 2.5 equivalents of water for 0.2 to 5 hours at -20C to 30C. A. Wagenaar teaches specific reaction conditions for relsted compounds in Recl. Trav. Chim.
Pays-Bas lQl, 91 (1982).
Alternatively, reaction of compounds of Formula (8), where R6 is H or benzyl, with a hypochlorite solution, Cuch as 5% NaOCl, can provide sulfonyl chlorides of Formula (5). Reaction conditions for similar reactions are obvious to one skilled in the art and are described in EP-A-142,152.
As shown in Equation 7, below, sulfonyl chlorides of Formula (5) may be prepared from the corresponding anilines of Formula (9) by a Meerwein reaction.
E~uation 7 ~ CtO)A
r~r 1. HCl, NIINO2, HOA~
~ ~ 2. ~o~. cucl2, ~o~
R~
~o) The aniline is diazotized and then reacted with ~ulfur dioside and cupric chloride analogous to the teachings of Yale and Sowinski, J. Org. Chem. 2~, 1524 (1960). Alternatively, the hydrochloride salts of anilines of Formula (9) can be diazotized in an organic solvent with an alkyl nitrite and reacted with sulfur dioside to give sulfonyl chlorides (5) ~naloqous to the teachings of M. Doyle, J. Org. Chem ~2, 2426,2431 (1977).

:........................ :

. W091/1~78 PCT/US91/01075 11 2~`, ~9 The pyrimidine carbamates of Formula (3) and the pyrimidine amines of Formula (6) are prepared by the method~ ~escribed and referenced in EP-A-72,347, EP-A-164,269, EP-A-173,498, U.S. Patent 4,540,782, anD U.~. Patent 4,666,506, herein incorporated by reference.
Agriculturally suitable salts of compounds of l~ Formula I are also useful herbicides and can be prepared in a number of ways known to the art. For e~ample, 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 lS basic anion (e.g., hydroside, alko~ide, carbonate or hydro~ide). ~uaternary amine salts can be made by similar techniques.
Salts of compounds of Formula I can also be prepared by eschange of one cation for another.
Cationic e~change can be effected by direct contact of an agueous ~olution 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 ~æ most efective when the desired salt containing the e~changed cation is insoluble in water and can be separated by filtration.
E~change may also be effecte~ by passing an agueou~ ~olution of a ~alt of a compound of Formula I
~e.g., an alkali metal or quaternsry amine ~lt) through a column packed with a cation e~change resin containing the cation to be e~changed for that of the original salt and the desired product i8 eluted from the column. This method i5 particularly useful when the desired salt is water-soluble, e.g., a potassium, sodium or calcium salt.
Acid addition salts, useful in this invention, can be obtained by reacting a compound of Formula I

., ': , .
.; ,, , . - .

~s W091/1~78 PCT/US91/01075 2~ i9 12 with a suitable acid, e.g., p-toluenesulfonic acid, trichloroacetic acid or the like.
The preparation of the compounds of this invention i6 further illustrated by the following specific esamples. Temperatures are reported in degrees Celsius; abbre~iations for nuclear magnetic resonance (NMR) are: s ~ singlet, d , doublet, t _ triplet, m - multiplet, and peak positions are reported as parts per million d~wnfield from internal tetramethylsilane. Infrared (IR) peak positions are given in reciprocal centimeters (cm~l) and sh denotes a shoulder.
~L
Methyl 3-~Cyan~me~hy1)-2-nitrobenzoate To a stirred solution of potassium cyanide (6.2 g) in methanol ~100 mL) and wster (150 mL) at 0C was added an acetonitrile solution of methyl 3-~bromomethyl)-2-nitrobenzoate (24.9 9).
catalytic amount of 18-crown-6 ether was then added.
After stirring overnight at room temperature, the reaction wos estracted with ethyl acetate. The combined estracts were washed with a brine solution, dried over magnes~um sulfate, filtered, concentrated, and chromatogr~phed on s~lica gel eluting with 20%
thyl acetate in he-anes to give 8.5 9 of the title compound as a white sol~d.
90 MHz NMR ~CDC13) ~: 3.83 (s, 2H, CH2):
3.93 (s, 3H, CH3); and 7.9 (m, 3H, arom.) ~X~EI.~
2-(Methosycarbonyl)-6-(cyanomethyl)-en~n~sulf~yl Chloride To a stirred suspension of dry tetrahydrofuran (150 mL) and 26~ potassium hydride in oil (6.66 g) was slowly added benzyl mercaptan (4.82 mL) at 0C
under a nitrogen atmosphere. After 15 minutes, methyl .

.. . .
. . ..

WO 9~ 478 pcr/us9l/o1o75 ' 3-(cyanomethyl)-2-nitrobenzoate (8.5 9) was ~dded and the resulting misture was stirred at room temperature 5 overnight. The reaction was contacted with 6N sodium hydro~ide (25 mL) and e~tracted with ethyl acetate.
The e~tracts were washed with a brine solution, dried over magnesium sulfate, filtered, and concentrated to give 9.0 9 of crude methyl 3-(cyanomethyl)-2-10 (phenylmethylthio)benzoate as a purple oil.
The crude thioether was stirred in a mi~cture ofdichloromethane (200 mL) and 6N hydrochloric acid (25 mL) at 0C, as 5% sodium hypochlorite (180 mL) was slowly added. The reaction mi~ture was then stirred 15 at 0C for 2 hours. The dichloromethane layer was washed with water, dried over magnesium sulfate, filtered, concentrated, and chromatographed on silica gel eluting with 25% ethyl acetate in hesanes to give 1.7 9 of the title compound as a yellow solid.
90 MHz NMR (CDC13) ~: 3.98 (s, 3H, CH~);
4.41 (s, 2H, CH2); and 7.83 (m, 3H, arom.).
E;x~lpLE 3 Methyl 3-(Cyanomethyl)-2-~[[(1,1-dimethylethyl)-dimethyls~lyllaminolsulfonyllbenzo~te A ~uspension of 2-(metho~ycarbonyl)-6-~cy~nomethyl)benzonesulfonyl chloride (10.7 9), amino-t-butyltlimethylsilane ~10.3 9), and sodium bicarbonate ~3.36 9) in dichloromethane (200 mL) was 30 stirrod at room temperature in a stoppered flask for 4 days. The organic phase was washed with with water, dried over magnesium sulfate, filtered, concentratea, and chromatographed on silica gel eluting with 30~ ethyl acetate in he~anes to give 5.0 35 g of the title compound as a yellow solid, m.p.
113-115C.
90 MHz NMR (CDC13) ~: 0.32 (s, 6H, SiCH3);
0.95 (s, 9H, C(CH3)3);

-.

wosl/1~78 PCT/US91/01075 i~ Z~

3.99 (8, 3H, OCH3);
4.42 (s, 2H, CH2CN);
5.91 (s, lH, NH);
7.6 (m, 2H, arom.); and 7.8 (m, lH, arom.).
IR (mineral oil) 3290, 2250, and 1710 cm~l.

Methyl 3-(Cyanomethyl)-2-tttt(4,6-dimethyl-2-pvrimidinyl~aminolcarbonyllaminolsulfonyllbenzQ~te A misture of methyl 3-~cyanomethyl)-2-[1[(1,1-dimethylethyl)dimethylsilyl]amino]-sulfonyl]benzoate (0.34 9), O-phenyl-N-(4,6-dimethyl-2-pyrimidinyl)carbamate ~0.24 9), and acetonitrile (2.5 mL) were stirred and cooled in an ice-acetone bath. A stock solution of 1 M tetrabutylammonium fluoride containing 8 mole % 1,8-diazabicyclo-t5.4.0]undec-7-ene (1.0 mL) was added and the reaction was stirred under a nitrogen atmosphere for 45 minutes. The reaction was added to water (30 mL) and acidified to pH S with lN hydrochloric acid. The resultinq procipitate was filtered, washed with water and h-~ane~, and a~r dried to give 0.23 9 of the tltle compound as a yollow solid, m.p. 182-185C.
200 MHz NMR ~DM80~ ~: 2.40 (s, CH, CH3);
3.79 (8, 3H, OCH3);
4.67 (8, 2H, CH2CN);
7.04 (8, lH, pyr~m. H);
7.64 (m, lH, arom.);
7.B2 ~m, 2H, arom.):
10.B (s, lH, NH); and 13.7 (s, lH, NH).
IR (mineral oil) 2240, 1740 cm~l.
E~EL~_~
~ethyl 3-Formv1-2-nitrohenzoate Methyl 3-(dibromomethyl)-2-nitrobenzoate (62.6 9), silver nitrate (109 9), 1,2-dimethosyethane (500 .. . . ~ ~ -,. . .

:' . ` . .
- , . . -,~, WO 91/15478 PCI`/US91/01075 ; ~.-,i ,. ~ .,: .
;~r ~g mL), and water (400 mL) were heated at reflus overnight. The undissolved salts were filtered off ~nd the filtrate was estrscted with ethyl acetate.
The estracts were washed with a brine solution, dried over magnesium sulfate, filtered, and concentrated to give a crude solid. Recrystallization from chlorobutane gave 20.9 9 of the title compound as an orange solid.
90 MHz NMR (CDC13) O: 3.98 (s, 3H, OCH3);
7.8 (m, lH, arom.);
8.3 (m, 2H, arom.); and 10.0 ~s, lH, HCO).
~x~oe~
Methyl 3-(Difluoromethyl~-2-nitrobenzo~te To a solution of diethylaminosulfur trifluoride (11 mL) in dichloromethane (75 mL) stirred at -70C
under a nitrogen atmosphere, was added a dichloromethane solution of methyl 3-formyl-2-nitrobenzoate (5.9 9). The reaction was allowed to warm to room temperature. After 3 hours it was poured onto ice (300 mL) and estracted with dichloromethane. The estracts were washed with wator, dried over magnesium ~ulfate, filtered, and conc-ntrat-d to ~i~o a crude ~olid. Recrystalli-zat~on from hesanes-chlorobutane ga~e 3.94 g of the title compound as ~ peach-colored ~olid, m.p. 66-69C.
90 MHz NMR (CDC13) ~: 3.94 (s, 3H, OCH3);

6.87 (t, lH, CHF2); and 7.9 (m, 3H, arom.).
E~pLE 7 2-(Methosycarbonyl)-6-~difluoromethyl)-.~enzene~LQ~yl Chlo~g~
To a stirred ~uspension of dry tetrahydrofuran (250 mL) and 26~ potassium hydride in oil (6.17 g) was slowly added benzyl mercaptan (4.63 mL) at 0C
under a nitrogen atmosphere. After 15 minutes, . . ..
~'` ` ~ . ', ' , r"
.

d 2~
methyl 3-(difluoromethyl)-2-nitrobenzoate (7.5 9) was added, and the resulting misture was 6tirred at room temper~ture overnight. The re~ction w~s cont~cted with ~queous sodium bicarbonate (50 mL) and estracted with ethyl acetate. The estracts were dried over magnesium sulfate, filtered, and concentrated to give 10.8 9 of crude methyl 3-(difluoromethyl)-2-(phenylmethylthio)benzoAte as a brown oil.
The crude thioether was 6tirred in a misture of dichloromethane (400 mL) and 6N hydrochloric acid (28 mL) at 0C, as 5% sodium hypochlorite (204 mL) was slowly added. The reaction misture was stirred at 0C for 2.5 hours. The dichloromethane layer was washed with water, dried over magnesium 6ulfate, filtered, concentrated, and triturated with hesanes to give 5.17 9 of the title compound as a yellow solid.
90 MHz NNR (CDC13) ~: 4.13 (s, 3H, OCH3); and 7.1 - 8.3 (m, 4H, CHF2 and nrom.).

Methyl 3-(Difluoromethyl)-2-[t[(l,l-dimethyl-ethyl~dimethyls~lyllaminolsulfonyllbenzQate A su~pension of 2-(methosycarbonyl)-6-(difluoro-mothyl)b-nzenesulfonyl chloride ~5.17 9), am~no-t-butyldimethylsilano ~4.9 9), and 60aium bicarbonate ~1.5 9) in dichloromethane ~150 mL) was stirred at room temperature in z stoppered flask for 4 days. The organic phase was washed with water, dried over magne~ium sulfate, filtered, concentrated, and chromatographed on silica gel eluting with 10 %
ethyl acetate in hesanes to give 2.23 9 of the title compound a~ a white solid.
90 MHz NMR ~CDC13) t: 0.2 ~s, 6H, SiCH3);
O.B7 (s, 9H, C(CH3)3);
3.90 (8, 3H, OCH3);
-;

` ~, .

~ wos1/~78 PCT/US91/01075 ,, ~.
17 ~ 9 5.8B (s, lH, NH); and 7.20 - 8.36 (m, 4H, CHF2 and arom.).
EXAMPLE_2 Methyl 3-(Difluoromethyl)-2-~[[[(4-metho~y-2-~yrim~ mu~n1carbonyllaminolsulfonyllbenzoate A mi~ture of methyl 3-(difluoromethyl)-2-[[[(l,l-dimethylethyl)dimethylsilyl]amino~sulfonyl]-benzoate (0.22 9~, O-phenyl-N-64-methosy-2-pyrimidinyl)carbamate (0.15 9), and acetonitrile (2.0 mL) were stirred and cooled in an ice-acetone bath. A stock solution of 1 M tetrabutylammonium fluoride containing 8 mol % 1,8-diazabicyclo-15.4.0]undec-7-ene (0.61 mL) w~s added, and the reaction was stirred under a nitrogen atmosphere for 1 hour. The reaction was added to water (30 mL) snd acidified to pH 5 with lN hydrochloric acid. The resulting precipitate was filtered, washed with water and he~anes, ana air dried to give 0.06 9 of the title compound as a white solid, m.p. 178-180C
(decomposition).
200 MHz NMR (DMSO) 6: 3.94 (s, 3H, OCH3);
4.14 (8, 3H, OCH3);
6.87 ~d, lH, pyrim. H);
7.8 - 8.2 ~m, 3H, arom.~;

8.43 ~d, lH, pyrim. H);
11.46 ~s, lH, NH); and 13.90 ~s, lH, NH).
IR ~mineral oil) 1?30, 1720 cm~l.
~E~E~Q
Met~yl 3-(1-Hydro~yethyl)-2-ni~bgLz~te Titanium tetrachloride ~6.25 mL) was added to dry diethylether (250 mL) at -78C and was stirred under a nitrogen atmosphere. The resulting yellow Juspension was allowed to warm to -50C and was recooled to -78C prior to adding 1.4 molar .. .. . .
- - : : , , . -- . . .
.. - ..... . . .
, W091/154~8 PcT/~S91/0107s ,',' ~.

methyllithium in diethylether (41.6 mL). The misture was warmed to -30C and the resulting purple misture w~s cooled to -60C and transferred by cannula into an adjacent fl~sk containing methyl 3-formyl-2-nitrobenzoate (11.6 g) and dry tetrahydrofuran (250 mL). The resulting mi~ture was allowed to warm to room temperature and was stirred under a nitrogen atmosphere for about 18 hours. The reaction w~s poured onto a mi~ture of ice (100 mL) and ~N
hydrochloric acid (100 mL) and e~tracted with ethyl acetate. The e~tr2cts were washed with saturated sodium bicarbonate and brine, dried over magnesium sulfate, filtered, ~nd concentrated to a crude oil.
Flash column chromatography on silica gel, eluting with dichlorometh2ne gave 9.8 g of the title compound as a yellow oil, nD 1.5309.
90 MHz NMR (CDC13) ~: 1.47 (d, 3H, CH3);
2.58 (s, lH, OH);
3.92 (s, 3H, OCH3);
4.93 (m, lH, CH); and 7.8 (m, 3H, arom.).
IR (neat) 3431, 1735 cm~l.
2S ~MPLE 11 Pethyl 3~ luoroethvl)-2-nitrobenzoate To a ~olution o diethylamino sulfur trifluoride ~18 mL), in dichloromethane (100 mL), stirred at -74C under a nitrogen atmosphere was added a dichloromethane solution of methyl 3-(1-hydro~yethyl)-2-nitrobenzoate (14.6 9). The reaction was allowed to warm to room temperature and was briefly warmed to 35C. After a 4 hour reaction period, the reaction was poured onto ice and water ~200 mL) and e~tracted with dichloromethane. The combined e~tracts were washed with a 1:1 mi~ture of lN NaOH and saturated sodium bicarbonate, dried o~er magnesium sulfate, filtered, and concentrated to give ':

. ~ ' -. :
- - -wosl/15478 PCT/US91/01075 ~' 19 , ,, 11.3 9 of the title compound as a dark amber oil, nD
1.5151.
90 MHz NMR (CDC13) ~: 1.67 (d of d, 3H, CH3);
3.93 (s, 3H, OCH3);
5.7 (d of q, lH, CHF); and 7.9 (m, 3H, arom.).
IR (neat) 1736 cm~l.
~
Methyl 3-(1-Fluoroethyl)-2-(Dhenylmeth~lthio)benzoate Following the procedure described in Esample 2, methyl 3-(1-fluoroethyl)-2-nitrobenzoate (15 9) was reacted to give 17.55 g of the unpurified title compound as a brown oil.
~AMPLE 13 2-(Methosycarbonyl)-6-(1-fluoroethyl)-benzene sulfonyl Chloride Following the procedure described in E~ample 2, methyl 3-(1-fluoroethyl)-2-(phenylmethylthio)benzoate (8.8 9) was reacted and chromatographed on silica eluting with 10% ethyl acetate in hesanes to give 1.7 g of the title compound as an orange oil.
90 MHZ NMR (CDC13) ~: 1.8 (d of d, 3H, CH3);
4.0 ~s, 3H, OCH3);
6.6 ~d of q, lH, CHF); and 7.8 ~m, 3H, arom.).
E~.
Methyl 3-(l-Fluoroethyl)-2-lt[~l~l-dimeth ethyl~dimethYlsilyllaminolsulfonyllbe~pzQ~
Following the procedure described in Esample 3, 2-~methosycarbonyl)-6-~1-fluoroethyl)benzene sulfonyl chloride (2.q 9) was reacted and chromatographed on silica eluting with 15% ethyl acetate in hesanes to give 1.3 9 of the title compount as an orange oil.

, . . - ~ -:
.

; .
... ,., . . . : ., . - . , .
: ~ - . .. :
~ . .

.

WO91/1~78 PCT/US91tO1075 ~9 20 90 MHZ NMR (CDC13) 6: 0.17 (s, 3H, SiCH3);
0.24 (s, 3H, SiCH3);
0.84 (s, 9H, C(CH3)3);
1.57 (d of d, 3H, CH3):
3.88 (s, 3H, OCH3);
5.83 (s, lH, NH);
6.6 (d of g, lH, CHF); and 7.6 (m, 3H, arom.).
~XA~.E~
Methyl 3~ Fluoroethyl)-2-[[[[(4,6-dimetho~y-2-pyrimidinyl~aminolcarbonyllaminols~lf~nyllbenzoate Following the procedure described in E~ample 4, methyl 3-(l-fluoroethyl)-2-[[[(l,l-dimethylethyl)-dimethylsilyl]amino]sulfonyl]benzoate (0.26 9) and O-phenyl-N-(4,6-dimetho~y-2-pyrimidinyl)carbamate (0.2 g) were reacted to give 0.16 9 of the title compound ~s a pink solid, m.p. 155-158C
(decomposition).
200 MHz NMR (DMSO) 6: 1.64 (d of d, 3H, CH3);
3.B5 (s, 3H, CO2CH3);
3.9B (s, 6H, OCH3);
6.0B (s, lH, pyrim. H);
7.04 (d of q, lH, CHF);
7.72 (m, lH, arom.);
7.96 (m, 2H, arom.);
10.85 (8, lH, NH); nnd 12.75 (5, lH, NH).
IR (mineral oil) 32Bl, 173B, 1722 cm~l.
~ y applying the procedures of Eguations 1 throu~h 7 and Esamples 1 through 15, the compounds in T~bles 1 throl~gh 4 can be readily prepared by one skilled in the art.

.
.
, - .., ...

.

~., wos1/1~78 PCT/US91/01075 ~, ,.

;, 2~ i ~Ç~

~O NHCNH J~

Rl is CH3 Rl is CH2CH3 R2 ~ y ~2 X Y

CH2F OCH3 Cl CH2F OCH3 Cl CHF2 OCH3 Cl CHF2 OCH3 Cl ..
~: , . '' . . ' ' , . ................ .
- , ~

, ~ , , . .~ . .

W091/2~78 PCT/US91/0107S

Rl is CH3 Rl is CH2CH3 R2 2~ Y B2 ~ y CH2CN OCH3 H CH2CN OCH~ H
CH2CN OCH3 Cl CH2CN OCH3 Cl CHFCH3 CH3 OCHF2 CHFcH3 CH3 OCHF2 CHFCH3 OCH3 Cl CHFCH3 OCH3 Cl R~ CH2CH2CH3 Rl ~ 8 CH(CH3)2 B2 2~ Y ~2 ~ y CH2F C~3 CH3 CH2F CH3 CH3 .
::

;
.:

WO91/1~78 PCT/US91/01075 ;~f~ ~ 95"9 Rl is CH2 Q2CH3 Rl i5 CH(CH3)2 B2 ~ y B2 ~ y CH2F OCH3 Cl CH2F OCH3 Cl CHF2 OCH3 Cl CHF2 OCH3 Cl CH2CN OCH3 Cl CH2CN OCH3 Cl CHFCH3 CH3 OCH3 CHFCH3 CH3 OC~3 CHFCH3 OCH3 Cl CHFCH3 OCH3 Cl .

.

. ' ' , , '- , ' .
'. . ' ' . ~' ,, ~ ' . ' , ' , . . ' ' , .
. . . , " W091/1~78 PCT/US91/01075 Rl is CH2CH2CH3 Rl is CH(CH3)2 Rl is CH2CH-CH2 Rl is CH2CH2Cl B2 ~ Y B2 a~ Y

CH2F OCH3 H CH2F OCH3 Cl CH2F OCH3 Cl CH2F OCH3 C2H5 CHF2 OCH3 H CHF2 OCH3 Cl CHF2 OCH3 Cl CHF2 OCH3 C2H5 CH2CN OCH3 H CH2CN OCH3 Cl CH2CN OCH3 Cl CH2CN OCH3 C2H5 ' .
.. , .......... ' , . - - : . .

WO91/1~78 PCT/US91/01075 ~ ,, " -, ., .:
2~ 9 Rl is CH2CH-CH2 Rl is CH2CH2Cl a2 x Y B2 2~ Y

CHFCH3 OCH3 H CHFC~3 OCH3 H
CHFCH3 OCH3 Cl CHFCH3 OCH3 Cl Rl is CH2C-CH Rl is CH2CH2OCH3 R2 2~ Y B2 2~ Y

CH2F OCH3 H CH2F OCH3 Cl CH2F OCH3 Cl CH2F OCH3 C2H5 CHF2 OCH3 H CHF2 OCH3 Cl CHF2 OCH3 Cl CHF2 OCH3 C2H5 - . .. -, ,.. . , , . : ,. : - - . . - - . .

.. , , . .. . . . , ...... . - .
' :: , ' : , ' ' ' :' ' .' '.' . ' ' -. - : . ..

.. . ..

wos1/l~7x PCT/US91/01075 Rl is CH2C_CH Rl is CH2CH20CH3 ~2 ~ Y B2 ~ y CH2CN OCH3 H CH2CN OCH3 Cl CH2CN OCH3 Cl CH2CN OCH3 C2H5 CHFCH3 CH3 OCHF2 CHFcH3 CH3 OCHF2 CHFCH3 OCH3 Cl CHFCH3 OCH3 Cl . . - - , .
. .
:~' , . . :. . ' .
. - - - : . . :
. . . . . .: - . ... .. . .
: . , " ~ .

--.
-. ~ - : - : - .

. WO 91/15478 PCr/US91/010~5 ;~i J 3~9 ,., ~

~I.P~L

[~S02 HS i R3R4 R 5 r~C02R1 IRI R~ R3 a~ RS

CH3 C(CH3)3 CH3 C(CH3)3 CH3 C(CH3)3 3 CH3 C(CH3)3 CH2CH3 CH2F CH2CH3 CH2F CH3 CH3 C(CH3)3 CH2CH3 CHF2 CH2CH3 CHF2 CH3 CH3 C(CH3)3 CH2CH3 CH2CN CH2CH3 CH2CN CH3 CH3 C(CH3)3 CH2CH3 CHFCH3 CH2CH3 CHFCH3 CH3 CH3 C(CH3)3 CH2CH2CH3 CH2F CH2CH2CH3 CH2F CH3 CH3 C(CH3)3 CH2CH2CH3 CHF2 CH2CH2CH3 CHF2 CH3 CH3 C(CH3)3 CH2CH2CH3 CH2CN CH2CH2CH3 CH2CN CH3 CH3 C(CH3)3 CH2CH2CH3 CHFCH3 CH2CH2CH3 CHFCH3 CH3 CH3 C(CH3)3 CH(CH3)2 CH2F CH(CH3)2 CH2F CH3 CH3 C(CH3)3 CH(CH3)2 CHF2 CH(CH3)2 CHF2 CH3 CH3 C(CH3)3 ; ~ `
, . ' ~, .

' WO91/1~78 PCT/US91/01075 ' 2~`~J~ 9 28 Bl B2 ¦~1 R2 R3 R4 B5 CH(CH3)2 CH2CN CH(CH3)2 CH2CN CH3 CH3 C(CH3)3 CH(CH3)2 CHFCH3 CH(CH3)2 CHFCH3 CH3 CH3 C(CH3)3 CH2CH-CH2 CH2F CH2CH-CH2 CH2F CH3 CH3 C(CH3)3 CH2CH-CH2 CHF2 CH2CH-CH2 CHF2 CH3 CH3 C~CH3)3 CH2CH-CH2 CH2CN CH2CH-CH2 CH2CN CH3 CH3 C(CH3)3 CH2CH'CH2 CHFCH3 CH2CH'CH2 CHFCH3 CH3 CH3 C(CH3)3 CH2C-CH CH2F CH2C--CH CH2F CH3 CH3 C(CH3)3 CH2C--CH CHF2 CH2C-CH CHF2 CH3 CH3 C(CH3)3 CH2C_CH CH2CN CH2C-CH CH2CN CH3 CH3 C(CH3)3 CH2C--CH CHFCH3 CH2C-CH CHFCH3 CH3 CH3 C(CH3)3 CH2CH2Cl CH2F CH2CH2Cl CH2F CH3 CH3 C(CH3)3 CH2CH2Cl CHF2 CH2CH2Cl CHF2 CH3 CH3 C(CH3)3 CH2CH2Cl CH2CN CH2CH2Cl CH2CN CH3 CH3 C(CH3)3 CH2CH2Cl CHFCH3 CH2CH2Cl CHFCH3 CH3 CH3 C(CH3)3 CH2cH2ocH3 CH2F CH2cH2ocH3 CH2F CH3 CH3 C(CH3)3 CH2CH2OcH3 CHF2 CH2CH2OcH3 CHF2 CH~ CH~ C(CH3)3 CH2CH2OCH3 CH2CN CH2CH2OCH3 CH2CN CH3 CH3 C(CH3)3 CH2cH2ocH3 CHFCH3 CH2CH2OCH3 CHFCH3 CH3 CH3 C(CH3)3 .. : ~
: . :
. . - .. ~ :, - .

.::
- - , - :
.

~ WO9i/1~78 PCT/US91/01075 29 2~' ~ ~9 TABLE_~.

~ ..

B2 X Y B2 2~ Y

CH2F CH3 OCH3 CH~CN CH3 OCH3 CH2F OCH3 Cl CH2CN OCH3 Cl CHF2 OCH3 Cl CHFCH3 OCH3 Cl . .
.
'' ` '. ' ' ', ' ' : - .. . ' ' . ~ ~ .

'` : .

~ wosl/1~78 PCT/US91/01075 Fo r~ a t i on~
Useful formulations of the compounds of Formula 1 can be prepared in conventional ways. They include dusts, gr~nules, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates and the like. Many of these may be applied directly. Sprayable formulations can be e~tended in suitable media and used at spray volumes of from a few liters to se~eral 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 acti~e ingredient(s) and at least one of (a) about 0.1% to 20% surfactant(s) ana (b) about 1%
to 99.9% solid or liquid inert diluent~s). More specifically, they will contain these ingredients in the following appro~imate proportions:
Weight Percent~
Active Inaredient Diluent(s) Surfactant(s) Wettable Powders20-90 0-74 1-l0 Oil 8uspensions,3-50 40-95 0-15 Emul~ions, Solutions, (including Emulsifiable Concentrates) Aqueous Suspension 10-50 40-84 1-20 Dusts 1-25 70-99 0_5 Granules and Pellets 0.1-95 5-99,9 0-15 High Strongth90-99 O-10 0-2 Compositions ~ Active ingredient plus at least one of a Surfactant or a Diluont oquals 100 weight percent.

- , ' .

, W091/15478 PCT/US91/01075 , ~, z~, ~.~;~9 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 surfaotant to active ingredient are some-times desirable, and are achieved by incorporation into the formulation or by tank mi~ing.
Typical ~olid diluents are described in Watkins, et al., ~Handb~ok of Insecticide Dust Diluents and Carriers~, 2nd Ed., Dorland Books, Caldwell, New Jersey, but other solids, either mined or manufac-tured, may be used. The more absorptive diluents are preferred for wettable powders and the denser ones for lS 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 ~uspension concentrates; solution concentrates are preferably stable against phase separation at 0C. ~McCutcheon~s Detergents and Emulsifiers Annual~, MC Publishing Corp., Kidgewood, New Jersey, as well as Sisely and Wood, ~Encyclopedia of Surface Active Agents~, Chemical Publishing Co., Inc., New York, 1964, list surfactants and recommended uaes. All formulatlons can contain minor amounts of additi~es to roduce foaming, caking, corrosion, microbiological growth, etc.
The methods of making such compositions are well known. Solutions are prepared by simply mi~ing the ingredient8. Fine solid compositions are made by blending and, usually, grinding a8 in a hammer or fluid energy mill. Suspensions are prepared by wet milling ~see, for e~ample, Littler, U.S. Patent 3,060,084). Granules and pellets may be made by spraying the active material upon preformed granular carriors or by agglomeration techniques. See J. E.
Browning. ~Agglomeration~, Chen~cal En9in~e~ 9~
December 4, 1967, pp. 147ff. and ~Perry~s Chemical -.. . .. . .

`

WO91/l~78 PCT/US91/01075 ,~
--*-9 32 Engineer~s Handbook~, 5th Ed., McGraw-Hill, New York, 1963, pp. 8-57ff.
For further inform~tion reg~rding the art of formulotion, see for e~ample:
H. M. Lous, U.S. Patent 3,235,361, February 15, 1966, Col. 6, line 16 through Col. 7, line 19 and E~amples 10 through 41;
R. W. Luckenbaugh, U.S. Patent 3,309,192, March 14, 1967, Col. 5, line 43 through Col.
7, line 62 and Examples 8, 12, 1~, 39 t 41, 52, 53, S8, 132, 138-140, 162-164, 166, 167 and 169-182;
H. Gysin ~nd E. Xnusli, U.S. Patent 2,891,855, June 23, 1959, Col. 3, line 66 through Col. 5, line 17 and E~amples 1-4;
G. C. Xlingman, ~Weed Control as a Science~, John Wiley and Sons, Inc., New York, 1961, pp. 81-96; and J. D. Fryer ana S. A. Evans, ~Weed Control ~andbook~, 5th Ed., Blackwell Scientific Publications, O~ford, 1968, pp. 101-103.
In the following esamples, all parts are by weight unless otherwl~e inDicated.
~sa~le A
H~gh ~tren~th Concentrate Methyl 3-(cyanomethyl)-2-t[11(4,6-dimethyl-2-pyrimiDinyl)amino]carbonyl]amino]-30 ~ulfonyllbonzoate 9 trimethylnonyl polyethylene glycol ether 1~
The ~urfactant is sprayed upon the activeingredient in a blenDer and the misture sifted through a U. ~. S. No. 40 sieve (0.42 mm openings) prior to packaging. The concentrate may be formulated further for practical use.

.' ' ~ ' ' .

: :. . . . : . - :
.. . : - .: -: : :

W091/1~78 PCT/US91/01075 E~ample B
Wettabl~ Pow~r 5 Methyl 2-1[~(4-chloro-6-methosy-2-pyrimidinyl)-Jmino]carbonyl]amino]sulfonyl~-3-(cyanomethyl)-benzoate 65~
dodecylphenol polyethylene glycol ether Z%
sodium ligninsulfonate 4~
10 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 sie~e (0.3 mm opening) and packaged.
E~ample C
20 A~ueous Suspension Methyl 3-(cyanomethyl)-2-~ (4-(difluoro-metho~y)-6-metho~y-2-pyrimidinyl]amino]-carbonyl]amino]sulfonyl]benzoate 50.0%
polyacrylic acid thickener 0.3%
25 dodecylphenol polyethylene glycol ether 0.5%
disodium phosphate 1%
monosodium phosphate 0.5%
polyvinyl alcohol ~ 1.0%
water 56.7%
The ingredient6 are blended and ground together in a sand mill to produce particles essentially all under 5 microns in size.
E~ample D
Oil Suspension Methyl 3-(difluoromethyl)-2-~[~(4-methosy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]-benzoate 35 wo9l/ls478 P~T/US91/01075 Z~i, ~ 9 34 blend of polyalcohol carbo~ylic esters and oil soluble petroleum sulfonates 6~
5 sylene 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, e~tended with oils, or emulsified in water.
Example E
Oil Sus~ension Methyl 3-(fluoromethyl)-2-[[[[~4-methosy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]-benzoate 25%
15 polyosyethylene sorbitol hesaoleate 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 e~tended with oils or emulsified in water.
Esam~le F
Agueous Susoension Methyl 2-[[[[(4,6-dimetho~y-2-pyrimidinyl)amino]-carbonyl]amino]sulfonyl]-3-(fluoromethyl)-benzoate 25%
hydrated ottapulgite 3%
crude calcium ligninsulfonate 10~
sodium dihydrogen phosphate 0,5%
water 61.5%
The ingredients are ground together in a ball orroller mill until the solid particles ha~e been reduced to diameters under 10 microns.
EsamDle G
Wettable Powder Ethyl 2-[[[[(4-chloro-6-methosy-2-pyrimidinyl)-amino]carbonyllamino]sulfonyl]-3-(fluoromethyl)-benzoate qo,o~

. ` ` ' '.
.

' ". ... .
~f ~r9 ~, .. .
dioctyl sodium sulfosuccinate 1.5%
sodium ligninsulfonate 3%
5 low viscosity methyl cellulose 1.5%
att~pulgite 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.
E~ample H
Granule 15 wettable powder of E~ample G 15~
gypsum 69%
potassium sulfate 16%
The ingredients are blended in a rotating miser and water sprayed on to accomplish granulation. When most of the material has reached the desired range of 1.0 to 0.42 cm (V.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 25 ingredient.
8~m~
We~ Powder Methyl 2-[[1[(4,6-dimethosy-2-pyrimidinyl)amino]-carbonyl]amino]sulfonyl]-3-(fluoromethyl)-30 benzoate 50~
sodium alkylnaphthalenesulfonate 2%
low viscosity methyl cellulose 2~
diatomaceous earth 46%
The ingredients are blended, coarsely hammer-milled and the air milled to produce particles ofactive essentially all below 10 microns in diameter.
~he product is reblended before packaging.

WO91/1~78 PCT/US91/01075 ~t~ ellet 5 Methyl 3-(fluoromethyl)-2-[[[[(4-methosy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]-benzoate 25 anhydrous sodium sulfate 10%
crude calcium ligninsulfonate 5%
10 sodium alkylnaphthalenesulfonate 1 calcium/magnesium bentonite 59%
The ingredients are blended, hammer-milled and then moistened with about 12% water. The mi~ture is estruded 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 (O.B4 mm openings). The granules held on a U.S.S. No. 40 sieve (0.42 mm openings) may be packaged for use and the 20 fines recycled.
E~ample X
Wettable Powder Methyl 3-~difluoromethyl)-2-[[[[~4-methosy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]-25 benzoate 80~
~odium alkylnaphthalenesulfonate 2%
sodium lign~nsulfonate 2%
synthetic amorphous s~lica 3%
kaolinite 13%
The ingredients are blended and then ground in a hammermill to produce particles with an average particle si~e less than 25 microns in diameter. The material is reblended and sifted through a U.S.S. No.
50 Yieve ~0.3 mm opening) before being packaged.

, . --; WO91/1~7g PCT/~S91/01~75 .j ,., ~
37 ~ r~9 E~Q1-Hi~h Strength Concentrate Methyl 3-(cy~nomet~yl)-2-[[[[(4~(difluorometho~y)-6-metho~y-2-pyrimidinyl]amino]carbonyl]amino]-sulfonyl]benzoate 98.5 silica aerogel 0.5 ~ynthetic 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.
E~amPlQ_~

Methyl 3-(cyanomethyl)-2-[[[[(4,6-dimethyl-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]-benzoate, sodium salt 5%
20 water 95 The salt is added directly to the water with stirring to produce the solution, which may then be packaged for use.

25 ~1~115Y
Test results indicate that compound6 of this invention are active postemergence and preemergence herbicides. Many compounds of this invention are useful for the control of selected grass and broad-leaf weeds with tolerance to important argonomic cropssuch as barley (Hordeum vulgare), corn (Z~a mgy~)~
rice (QrYza ~iY~)~ and wheat (Triticym aestivum).
Grass weeds controlled include, but are not limited to, barnyardgrass (Ecbinn$hlg~ crus-~alli), black-grass (Alo~ecurus myosuroides), Bromu~ spp., fo~tail(Setaria spp.), johnsongrass (sorohum hal~pense), panicum (Panicum spp.), and wild oat (Avena fatua).
Broadlea~ weeds controlled include, but are not ~' 2 ~ imited to, cocklebur (Xanthium Densylvanicum), jimsonweed (Datura ~tramonium), lambsquarters (Cheno~odium ~l~m), morningglory (I~omoea spp.), pigweed (~m~L~n~h~ spp.), Polyconum spp., sicklepod (Cassia obtusifolia), and velvetleaf (A~il~n theophrasti). Many compounds in this invention also control nutsedge (Cy~erus spp.). Several compounds from this invention sre particularly useful for weed control in cereal crops such as barley and wheat. A
select few of these compounds are particularly useful for weed control in corn.
Several compounds in this invention have utility in non-crop areas where selected or complete control of plants or weeds is desired, 6uch as around storage tanks, parking lots, billboards, highways, and railroad structures. These compounds are also useful in fallow areas of crop production such as in wheat and barley and in planta~ion crops such as palm, banana, citrus, rubber, etc. Alternatively, these compounds may be useful to modify plant qrowth or as citrus h~rvest aid abscission agents.
Rates of application for compounds of this invent~on are determined by a number of factors.
These factors include: formulation selected, method of ~ppl~cation, amount of ~egetation prcsent, growing conditions, etc. ~n general terms, the subject compounds should be applied at rates from 0.00l to 20 kg/ha with a preferred rate range of from 0.004 to 0.25 kg/ha. One skilled in the art can easily determine rates needed 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 WO9i/1~78 ~CT/US91/01~7S

......
39 ~9~ ~9 esemplifies some of the herbicides ~uitable for use in mistures. A combination of compounds from this invention with one or more of the following herbicides may be p~rticularly useful for weed control.

Common Name Chemical Name acetochlor 2-chloro-N-(ethosymethyl)-N-(2-ethyl-6-methylphenyl)acetamide acifluorfen 5-[2-chloro-4-(trifluoromethyl)-phenosy]-2-nitrobenzoic acid alachlor 2-chloro-N-(2,6-diethylphenyl~-N-(methosymethyl)acetamide lS anilofos 5-4-chloro-N-isopropylcarbaniloyl-methyl-O,O-dimethyl phosphorodi-thioate ametryn N-ethyl-N'-(l-methylethyl)-6-(methylthio~-1,3,5-triazine-2,4-diamine ami~role lH-1,2,4-triazol-3-amine AMS ammonium sulfamate asulam methyl [(4-aminophenyl)sulfonyll-carbamate 25 atrazine 6-chloro-N-ethyl-N'-(l-methylethyl)-1,3,5-triazine-2,4-diamine barban 4-chloro-2-butynyl 3-chlorocarbamate benefin N-butyl-N-ethyl-2,6-dinitro-4-(tri-fluoromethyl)benzenamine bensulfuron 2-[[[[[(4,6-dimethosy-2-pyrimi-methyl dinyl)aminolcarbonyl]-amino]Eulfonyllmethyl]benzoic acid, methyl ester bensulide O,O-bis(l-methylethyl) S-[2-[(phenylsulfonyl)amino]-ethyl]phosphorodithioate bentazon 3-(1-methylethyl)-(lH)-2,1,3-benzothiadiazin-4(3H)-one, 2,2-dio~ide , WO91/l~7X PCTtUS91/0107~
Y~
~~ ~ ~ 9 Common Name Chemical Name benzofluor N-[4-(ethylthio)-2-(trifluoro-methyl)phenyl]methanesulfonamide benzoylprop N-benzoyl-N-(3,4-dichlorophenyl)-DL-alanine bifenos methyl 5-(2,4-dichlorophenosy)-2-nitrobenzoate bromacil 5-bromo-6-methyl-3-(1-methylpropyl)-2,4(lH,3H)pyrimidinedione bromosynil 3,5-dibromo-4-hydrosybenzonitrile butachlor N-(butosymethyl)-2-chloro-N-(2,6-diethylphenyl)acetamide buthidazole 3-15-(1,1-dimethylethyl)-1,3,4-thia-diazol-2-yl~-4-hydrosy-1-methyl-2-imidazolidinone but-alin 4-(1,1-dimethylethyl)-N-(l-methyl-propyl)-2,6-dinitrobenzenamine butylate S-ethyl bis(2-methylpropyl)-carbamothioate cacodylic dimethyl arsinic oside acid 25 CDAA 2-chloro-N,N-di-2-propenylacetamide CDEG 2-chloroallyl diethyldithiocarbamate CGA 142,464 3-(4,6-dimethosy-1,3,5-triazin-2-yl)-1-[2-(2-methosyethosy)-phenyl-sulfonyl]-urea 30 chloramben 3-amino-2,5-dichlorobenzoic acid chlorbromuron 3-(4-bromo-3-chlorophenyl)-1-methosy-1-methylurea chlorimuron 2-[[[[(4-chloro-6-methosy-2-pyrimi-ethyl dinyl)amino]carbonyl]-amino]sulfonyl]benzoic acid, ethyl ester chlormethosy- 2,4-dichlorophenyl 4-nitro-3-nil methosyphenyl ether :, ` : ' ..

Commo~_~m~ Chemical_~ame chlornitrofen 2,4,6-trichlorophenyl-4-nitro-phenyl ether chlorosuron N'-[4-(4-chlorophenosy)phenyl]-N,N-dimethylurea chlorpropham l-methylethyl 3-chlorophenylcarbamate 10 chlorsulfuron 2-chloro-N-[[~4-methosy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]benzene-sulfonamide chlortoluron N'-(3-chloro-4-methylphenyl)-N,N-dimethylurea 15 cinmethylin eso-1-methyl-4-(1-methylethyl)-2-[(2-methylphenyl)methosy]-7-osabicyclo-[2.2.1]heptane clethodim (E,E)-(+)-2-[1-~1(3-chloro-2-propenyl)-osy]imino]propyl]-5-[2-(ethylthio)-propyl]-3-hydrosy-2-cyclohesen-1-one 20 clomazone 2-[(2-ch!or^pheny')methyl~-4,4-dimethyl-3-isosazolidinone cloprosydim (E,E)-2-[1-[[(3-chloro-2-propenyl)o~y)--imino]butyl]-5-[2-(ethylthio)propyl]-3-hydrosy-2-~yclohesen-1-one 25 clopyralid 3,6-dichloro-2-pyridinecarbosylic acid CMA calcium salt of MAA
cyanazine 2-[[4-chloro-6-(ethylamino)-1,3,5-tri-azin-2-yl]amino]-2-methylpropanenitrile 30 cycloate S-ethyl cyclohesylethylcarbamothioate cycluron 3-cyclooctyl-1,1-dimethylurea cyperguat l-methyl-4-phenylpyridinium cyprizine 2-chloro-4-(cyclopropylamino)-6-(iso-propylamino)-~-triazine . ..~

WO91/1~78 PCT/US91/01075 CommQ~ Na~ C~emical Name cyprazole N-[5-~2-chloro-1,1-dimethylethyl)-1,3,4-thiadiazol-2-yl~cyclopropanecarbos-amide cypromid 3',4'-dichlorocyclopropanecarbo~anilide dalapon 2,2-dichloropropanoic acid dazomet tetrahydro-3,5-dimethyl-2H-1,3,5-thia-diazine-2-thione DCPA dimethyl 2,3,5,6-tetrachloro-1,4-benzene-dicarbosylate desmediphan ethyl [3-[[(phenylamino)carbonyl]osy]-phenyl]carbamate desmetryn 2-(isopropylamino)-4-(methylamino)-6-(methylthio)-~-triazine diallate 5-(2,3-dichloro-2-propenyl)bis(l-methylethyl)carbamothioate 20 dicamba 3,6-dichloro-2-methosybenzoic ac~d dichlobenil 2,6-dichlorobenzonitrile dichlorprop (+)-2-(2,4-dichlorophenosy)propanoic acid 25 dichlofop (+)-2-[4-(2,4-dichlorophenosy)phenosy]-propanoic acid, methyl ester diethotyl N-(chloroacetyl)-N-(2,6-diethylphenyl)-glycine difenzoquat 1,2-dimethyl-3,5-diphenyl-lH-pyrazolium dimepiperate S-l-methyl-l-phenylethylpiperidine-l-carbothioate dinitramine N3,N3-diethyl-2,4-dinitro-6-(trifluoro-methyl)-1,3-benzenediamine dinoseb 2-(1-methylpropyl)-4,6-dinitrophenol diphenamid N,N-dimethyl-Q-phenylbenzeneacetamide 43 2 ~

Co~mQn Name Chemical Nam~

dipropetryn 6-(ethylthio)-N,N'-bis(l-methylethyl)-1,3,5-triazine-2,4-diamine diquat 6,7-dihydrodipyrido[1,2-a:2',1'-c]-pyrazinedium ion diuron N'-(3,4-dichlorophenyl)-N,N-dimethylurea 10 DNOC 2-methyl-4,6-dinitrophenol DPX-M6316 3-[[[[(~-methosy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]amino]sulfonyl]-2-thiophenecarbosylic acid, methyl ester 15 DSMA disodium salt of MAA
dymron N-(4-methylphenyl)-N'-(l-methyl-l-phenylethyl)urea endothall 7-o~abicyclo[2.2.1]heptane-2,3-dicarbos-ylic acid 20 EPTC S-ethyl dipropylcarbamothioate esprocarb S-benzyl-N-ethyl-N-(1,2-dimethyl)-(SC2957) propyl)thiolcarbamate ethalfluralin N-ethyl-N-(2-methyl-2-propenyl)-2,6-dinltro-4-(trifluoromethyl)-benzenamine ethofumesate (~)-2-ethosy-2,3-dihydro-3,3-dimethyl-5-benzofuranyl methanesulfonate fenac 2,3,6-trichlorobenzeneacetic acid 30 fenosaprop (~)-2-[4-[(6-chloro-2-benzosazolyl)osy]-phenosy]propanoic acid fenuron N,N-dimethyl-N'-phenylurea fenuron TCA Salt of fenuron and TCA
flamprop N-benzoyl-N-(3-chloro-4-fluorophenyl)-DL-alanine Wo91/15478 PCT/US91/01075 9 ~

Common Name ~hemical Name 5 fluazifop (~)-2-14-r[5-(trifluoromethyl)-2-pyri-dinyl]o~y]phenosy]propanoic acid fluazifop-P (R)-2-[4-[15-(trifluoromethyl)-2-pyri-dinyl]osy]phenosy]propanoic acid fluchloralin N-(2-chloroethyl)-2,6-dinitro-N-propyl-4-(trifluoromethyl)benzenamine fluometuron N,N-dimethyl-N'-[3-(trifluoromethyl)-phenyl]urea fluorochlor- 3-chloro-4-(chloromethyl)-1-[3-(tri-idone fluoromethyl)phenyl]-2-pyrrolidinone 15 fluorodifen ~-nitrophenyl ~,~,a-trifluoro-2-nitro-p-tolyl ether fluorogly- carbosymethyl 5-[2-chloro-4-(tri-cofen fluoromethyl)phenosy]-2-nitrobenzoate fluridone l-methyl-3-phenyl-5-13-(trifluoro-methyl)phenyl]-4(1H)-pyridinone fomesafen 5-12-chloro-4-(trifluoromethyl)phenosy]-N-(methylsulfonyl)-2-nitrobenzamide fosamine ethyl hydrogen (aminocarbonyl)-phosphate 25 glyphosate N-(phosphonomethyl)glycine halosyfop 2-14-113-chloro-5-(trifluoromethyl)-2-pyridinyl]osy]phenosy~propanoic acid hesaflurate potassium hesafluoroarsenate 30 hesazinone 3-cyclohesyl-6-(dimethylamino)-1-methyl-1,3,5-triazine-2,4(1H,3H)-dione imazametha- 6-(4-isopropyl-4-methyl-5-oso-2-benz imidazolin-2-yl)-m-toluic acid, methyl ester and 6-(4-isopropyl-4-methyl-5-oso-2-imidazolin-2-yl)-~-toluic acid, methyl ester - . ' . ' ':

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. 45 ~ r ~ ~J ~v ~9 Comm~Qn Nam~ Chemical Name imazapyr (~)-2-14,5-dihydro-4-methyl-4-(1-methyl-ethyl)-5-oso-lH-imidazol-2-yl]-3-pyridinecarbosylic acid imazaquin 2-[4,5-dihydro-4-methyl-4-tl-methyl-ethyl)-5-oso-lH-imidazol-2-yl]-3-quinolinecarbosylic acid imazethapyr (~)-2-[4,5-dihydro-4-methyl-4-(1-methyl-ethyl)-5-oso-lH-imidazol-2-yl]-5-ethyl-3-pyridinecarbosylic acid iosynil 4-hydrosy-3,5-diiodobenzonitrile isopropalin' 4-(1-methylethyl)-2,6-dinitro-N,N-dipropylbenzenamine isoproturon N-(4-isopropylphenyl)-N',N'-dimethylurea isouron N'-[5-(1,1-dimethylethyl)-3-isosazolyl]-N,N-dimethylurea isosaben N-13-(1-ethyl-1-methylpropyl)-5-isosazolyl]-2,6-dimetho~ybenzamide karbutilate 3-[[(dimethylamino)carbonyl]amino]-phenyl-(l,l-dimethylethyl)carbamate lactofen (~)-2-ethosy-1-methyl-2-o~oethyl 5-12-chloro-4-(trifluoromethyl)phenosy]-2-nitrobenzoate lenacil 3-cyclohesyl-6,7-dihydro-lH-cyclopenta-pyrim~dine-2,4(3H,5H)-dione linuron N'-(3,4-dichlorophenyl)-N-methosy-N-methylurea MAA methylarsonic acid MAMA monoammonium salt of MAA
MCPA (4-chloro-2-methylphenosy)acetic acid MCP~ 4-(4-chloro-2-methylphenosy)butanoic acid ' '-'' ' ' . ' ' ' ~ .
-- : .
' , ~

WO91/1~78 PCT/US91/0107~

~ `.. ..~ ~ ~ 9 ~ommon Name Chemical Name 5 MON 7200 S,S-dimethyl-2-(difluoromethyl)-4-(2-methylpropyl)-6-(trifluoromethyl)-3,5-pyridinedicarbothionate mecoprop (~)-2-(4-chloro-2-methylpheno~y)-propanoic scid 10 mefenacet 2-(2-benzothiazolylo~y-N-methyl-N-phenylacetamide mefluidide N-[2,4-dimethyl-5-1[(trifluoromethyl)-sulfonyl]amino]phenyl]acetamide methal- N-(2-methyl-2-propenyl)-2,6-dinitro-N-propalin propyl-4-(trifluoromethyl)benzenamide methabenz- 1,3-dimethyl-3-(2-benzothiazolyl)urea thiazuron metham methylcarbamodithioic acid methazole 2-(3,4-dichlorophenyl)-4-methyl-1,2,4-o~adiazolidine-3,5-dione metho~uron N'-(3-chloro-4-methosyphenyl)-N,N-dimethylurea metolachlor 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(2-methosy-1-methylethyl)acetamide 25 metribuzin 4-amino-6-(1,1-dimethylethyl)-3-(methyl-thio)-1,2,4-triazin-5~4H)-one metsulfuron 2-t[[t(4-methosy-6-methyl-1,3,5-tri-methyl azin-2-yl)amino]carbonyl~-amino]sulfonyl]benzoic acid, methyl ester 30 MH 1,2-dihydro-3,6-pyridazinedione molinate S-ethyl hesahydro-lH-azepine-l-carbo-thioate - .

.' ` ' ' ' ~ ' ' ' , , ' ' .
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, .. . .
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-- --WOgl/15478 PCT/~91/01075 Common ~a~e Chemical Name 5 monolinuron 3~ chlorophenyl)-1-methosy-1-methyl-urea monuron N'-(4-chlorophenyl)-N,N-dimethylurea monuron TCA Salt of monuron and TCA
10 MSMA monosodium salt of MAA
napropamide N.N-diethyl-2-(1-naphthalenylo~y)-propanamide naptalam 2-[(1-naphthalenylamino)carbonyl]-benzoic acid 15 neburon 1-butyl-3-(3,4-dichlorophenyl)-1-methyl-urea nitralin 4-(methylsulfonyl)-2,6-dinitro-N,N-dipropylaniline nitrofen 2,4-dichloro-1-(4-nitropheno~y)benzene nitrofluorfen 2-chloro-1-(4-nitrrphenosy)-4-(tri-fluoromethyl)benzene norea N,N-dimethyl-N'-(octahydro-4,7-methano-lH-inden-5-yl)urea 3a~,-4~,5~,7a,7a~-isomer norflurazon 4-chloro-5-(methylamino)-2-[3-(tri-fluoromethyl)phenyl]-3(2H)-pyridazinone oryzalin 4-(dipropylamino)-3,5-dinitro-benzenesulfonamide o~adiazon 3-[2,4-dichloro-5-(1-methylethosy)-phenyl]-5-(1,1-dimethylethyl)-1,3,4-osadiazol-2(3H)-one osyfluorfen 2-chloro-1-(3-ethosy-4-nitrophenosy)-4-(trifluoromethyl)benzene paraquat l,l'-dimethyl-4,4'-dipyridinium ion , wo9l/ls~78 PCT/US91/01075 5, ~ ~f~

Commo~ ~m~ Chemical Name 5 pebulate ~-propyl butylethylcarbamothioate pendimethalin N-(l-ethylpropyl)-3,4-dimethyl-2,6-dinitrobenzenamine perfluidone l,l,l-trifluoro-N-[2-methyl-4-(phenyl-sulfonyl)phenyl]methanesulfonamide phenmedipham 3-[(metho~ycarbonyl)amino]phenyl (3-methylphenyl)carbamate picloram 4-amino-3,5,6-trichloro-2-pyridine-carbo~ylic acid PPG-1013 5-[2-chloro-4-(trifluoromethyl~-pheno~y]-2-nitroacetophenone osime-O-acetic acid, methyl ester pretilachlor a-chloro-2,6-diethyl-N-(2-propo~y-ethyl)acetanilide procyazine 2-[t4-chloro-6-(cyclopropylamino)-1,3,S-triazine-2-yl]amino]-2-methylpropane-nitrile profluralin N-(cyclopropylmethyl)-2,6-dinitro-N-propyl-4-(trifluoromethyl)benzenamine prometon 6-methosy-N,N'-bis(l-methylethyl)-1,3,5-2S triazine-2,4-diamine prometryn N,N'-bis(l-methylethyl)-6-(methylthio)-1,3,5-triazine-2,4-diamine pronamide 3,5-dichloro-N-(l,l-dimethyl-2-propyn-yl)benzamide 30 propachlor 2-chloro-N-(l-methylethyl~-N-phenylacetamide propanil N-(3,4-dichlorophenyl)propanamide propazine 6-chloro-N,N'-bis(l-methylethyl)-` 1,3,5-triazine-2,4-diamine 35 propham l-methylethyl phenylcarbamate ' Wosl/l5478 PCT/US91/01075 ~9 Common Name Chemical Name prosulfalin N-[[4-(dipropylamino)-3,5-dinitro-phenyl]sulfonyl]-S,S-dimethylsulfil-imine prynachlor 2-chloro-N-(l-methyl-2-propynyl)acet-anilide 10 pyrazolate 4-(2,4-dichlorobenzoyl)-1,3-dimethyl-pyrazol-5-yl-D-toluenesulphonate pyrazon 5-amino-4-chloro-2-phenyl-3(2H)-pyridazinone pyrazosulfuron ethyl 5-[3-(4,6-dimetho~ypyrimidin-2-ethyl yl)ureadosulfonyl]-l-methylpyrazole-4-carbo~ylate quinclorac 3,7-dichloro-8-quinoline carbo~ylic acid quizalofop (~)-2-[4-[(6-chloro-2-quino~alinyl)-ethyl o~y]pheno~y]propanoic acid, ethyl ester 20 secbumeton N-ethyl-6-metho~y-N'-(l-methylpropyl)-1,3,5-triazine-2,4-diamine setho~ydim 2-[1-(etho~yimino)butyl~-5-[2-(ethyl-thio)propyl]-3-hydro~y-2-cyclohe~en-l-one 25 siduron N-(2-methylcyclohe~yl)-N'-phenylurea slmazine 6-chloro-N,N'-diethyl-1,3,5-triazine-2,4-diamine SK-233 1-(a,-dimethylbenzyl)-3-(4-methyl-phenyl)urea sulfometuron 2-[[[[(4,6-dimethyl-2-pyrimidinyl)-methyl amino]carbonyl]amino]sulfonyl]-benzoic acid, methyl ester TCA trichloroacetic acid tebuthiuron N-[5-(1,1-dimethylethyl)-1,3,4-thiadi-azol-2-yl]-N,N'-dimethylurea terbacil 5-chloro-3-(1,1-dimethylethyl)-6-methyl-2,4(lH,3H)-pyrimidinedione ,' ~

f,~":'-.i~ `~ J~3 50 Common Name Chemi~al Name terbuchlor N-(butosymethyl)-2-chloro-N-12-(1,1-dimethylethyl)-6-methylphenyl]-acetamide terbuthyl- 2-(tert-butylamino)-4-chloro-6-(ethyl-azine amino)-~-triazine 10 terbutol 2,6-di-~L~-butyl-~-tolyl methylcar-bamate terbutryn N-(l,l-dimethylethyl)-N'-ethyl-6-(methylthio)-1,3,5-triazine-2,4-diamine thiobencarb S-~(4-chlorophenyl)methyl] diethylcar-bamothioate triallate S-(2,3,3-trichloro-2-propenyl) bis(l-methylethyl)carbamothioate tribenuron 2-[[[[N-(4-metho~y-6-methyl-1,3,5-methyl triazine-2-yl)-N-methylamino]-carbonyl]amino~sulfonyl]benzoic acid, m~tnyl ester triclopyr [(3,5,6-trichloro-2-pyridinyl)-o~y]acetic acid tridiphane 2-(3,5-dichlorophenyl)-2-(2,2,2-trichloroethyl)o~irane trifluralin 2,6-dinitro-N,N-dipropyl-4-(tri-fluoromethyl)benzenamine tr~meturon l-(p-chlorophenyl)-2,3,3-trimethylpseu-dourea 30 2,4-D (2,4-dichloropheno~y)acetic acid 2,4-D~ 4-(2,4-dichlorophenosy)butanoic acid vernolate S-propyl dipropylcarbamothioate ~ylachlor 2-chloro-N-(2,3-dimethylphenyl)-N-(l-methylethyl)acetamide Herbicidal properties of the subject compounds were discovered in a series of greenhouse tests.
Test procedures and results follow.

wosl/1~78 PCT/US91i01075 ,~
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. 51 7 3 . ~ ~ 9 C(O)A X
~9~O)~NHCN~

A = OR~

CMPD Rl B2 8 Y m.p.(C) 4 CH2CH3 CH2CN OCH3 Cl 177-184 8 CH3 CH2CN OCH3 Cl 186-194 CH3 CH2CN OCH3 H 179-180(d) 14 CH2C~3 CH2F OCH3 Cl 168-172 CH3 CH2F OCH3 Cl 165-172 17 CH3 CH2F OCH3 H 166-167(d) . ' . ~,, ' wos1/ls478 PCT/US91/01075 ,,~,;r,g 52 CMPD ~1 R2 ~ y m. p . ( oc 18 CH(CH3)2 CH2CN CH3 OCH3 176-177 19 CH(CH3)2 CH2CN OCH3 OCH3 196-199 CH(CH3)2 CH2CN OCH3 Cl 196-200 21 CH(CH3)2 CH2CN OCH3 H 174-175 24 CH3 CHF2 OCH3 H 17B-180(d) 29 CH(CH3)2 CHF2 CH3 OCH3 174-176 CH(CH3)2 CHF2 OCH3 OCH3 177-180 31 CH(CH3)2 CHF2 OCH3 Cl 186-196 32 CH2CH3 CHF2 CH3 CH3 180-192(d) 34 CH3 CH2F CH3 CH3 180-182(d) CH3 CHF2 CH3 CH3 167-169(d) 36 CH2CH3 CHF2 OCH3 Cl 173-177 38 CH3 CHFCH3 CH3 CH3 149-153(d) 39 CH3 CHFCH3 OCH3 Cl 134-137~d) CH3 CHFCH3 CH3 OCH3 58-64(d) 41 CH2CH3 CHFCH3 OCH3 Cl lS3-156(d) CMPD ~ B2 ~ y m.p.(C) 42 N(CH3)2 CHFCH3 OCH3 OCH3 156-158 ,: , wosl/ls47X PCT/US91/01075 , ,~.;. :
J~,~9 TEST A
~eeds of barley (Hordeum vulaare), barnyardgrAss (~shi~hlQ~ crus-palli), cheatgrass (~LQm~ secalin~), cocklebur (Xanthiu_ ~ensylvanicum), corn (~ m~Y~), cotton (~o~syDium hirsutum), crabgrass (Diaitaria spp.), giant fostail (Setaria faberi), morningglory (IPomoea spp.), rice (Orvza sativa), sorghum (Sorahum bicolor), soybean (GlYcine m~), sugar beet (Beta vulaaris), velvetleaf (A~tilQn theQphrasti), wheat (Triticum aest~_), and wild oat (Avena f~) and purple nutsedge (Cyperus rotundus) tubers were planted and treated preemergence with test chemicals dissolved in a non-phytotosic solvent. At the same time, these crop and weed species were also treated with postemergence applications of test chemicsls. Plants ranged in height from two to eighteen cm (two to three leaf stage) for postemergence treatments. Treated plants and controls were maintained in a greenhouse for approsimately sisteen 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 i8 complote control. A dash (-) response means no test result.

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-WO 91/15478 PCI`/US91/01075 .~i ~ 57 2~;~
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TEST B
Seeds of barley (~QL~ vulgare), barnyardgr~ss (E~hinQchloa crus-aalli), blackgrsss (~lQ~ecu~s myo~uroide~), cheatgrass (~LQm~
secalinu5), chickweed (Stellaria ~ ), cocklebur (~anth,ium ~ensylv~nicum), corn (~ m~Y~, cotton (GossvDium his~um), crabgrass (Di~itaria spp.), bedstraw (Galium aparine), giant fostail (Setaria fab~ii), lambsquarters (ChenoDodium albu~), morningglory (IDomoea hederacea), rape (~assi~
n~), rice (Qryza ,sativa), sorghum (Sorghum bicolor), soybean (Glvcine m~), sugar beet (~Q~
vul~aris), velvetleaf (Abutilon theophrasti), wheat (T~i~icum aestivum), wild buckwheat (Poly~onum ~onvolvulu~), and wild oat (Avena fatua) and purple nutsedge (Cyperus,rotundus) tubers were planted and treated preemergence with test chemicals dissolved in a non-phytoto~ic solvent. At the same time, these crop and weed species were also treated with postemergence applications of test chemicals. Plants rsnged in height from two to eighteen cm (one to four lesf stoge) for postemergence treatments. Treated plantq and controls were maintained $n a greenhouse for twelve to ~l~teen days, after which all species were compared to controls and visually evaluated.
Plant response rstings, summarized in Table B, 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.

, WO91/15478 PCT/US91/01075 . ~.
59 2~9 Table B
COMPOUND
Rate (200 g/ha) 43 POSTEMERGENCE
Barley 8 Barnyardgrass10 Bedstraw 9 Blackgrass 10 Cheatgrass 9 Chickweed 10 Corn g Cotton 9 Crabgrass 6 Giant fo~t A i 1 9 Lambsquarters9 Morningglory10 Nutsedge 10 Rape 10 Rice 9 Sorghum 9 Soybean g Sugar beet 9 Velvetleaf 9 Wheat 9 Wild buckwheat 9 Wild oat 8 WO91/2~7~ PCT/US91/01~75 2~
Table B
COMPOUND
Rote (200 g/ha) 43 PREEMERGENCE
~arley B
Harnyardgrass 9 Bedstraw 9 Plackgrass 9 Cheatgrass 8 Chickweed 9 Corn g Cotton 8 Crabgrass 9 Giont fo~toil 9 Lambsquarters 9 Morningglory 9 Nutsedge 10 Rape 9 Rice 10 Sorghum 9 Soybean 9 Sugar beet 9 Velvetleaf 9 Wheat 9 Wild buckwheot 9 Wild oat 8 .,... :

, WO 91/15478 PCI`/-~3S91~01075 ..
61 ~ 9 Table B
COMPOUND
Rate (50 g/ha) 32 33 34 35 37 3B 39 40 41 42 43 POSTEMERGENCE
Barley 9 9 10 10 7 9 5 9 5 9 7 Barnyardgrass 9 10 10 9 9 9 10 9 9 10 9 Bedstraw10 9 9 10 9 10 10 10 10 10 7 Blackgrass9 10 10 9 9 9 9 9 8 9 9 Cheatgrass9 9 10 9 9 9 9 9 9 9 8 Chickweed 10 - - 10 10 10 9 10 9 10 9 Cocklebur 10 10 10 10 10 10 10 10 - 10 Corn 10 10 9 10 10 10 9 9 9 10 7 Cotton 9 9 10 10 9 10 10 9 10 9 9 Crabgrass 9 - - 9 4 10 5 4 O 5 4 Giant fo~tail 9 9 10 9 9 10 9 9 6 9 9 Lambsquarters 10 10 10 10 10 10 9 9 10 10 9 Morningglory 9 9 9 9 10 10 9 10 10 10 10 Nutsedge10 10 10 9 10 10 10 10 9 - 10 Rape 10 9 9 9 9 9 9 10 10 9 9 Rice 9 9 10 9 9 10 9 9 8 9 9 Sorghum 9 9 10 9 9 10 9 9 8 10 9 Soybean 9 9 9 9 9 9 9 9 9 9 9 Sugar beet 10 9 9 10 9 9 9 10 10 10 9 Velvetleaf 9 10 10 10 10 10 10 9 9 10 9 Who~t 9 9 9 9 8 9 4 9 5 9 8 W~ld buckwheat 10 10 10 10 10 10 10 10 10 9 7 Wild oat 9 9 10 9 7 9 8 9 7 6 5 ' WO 91/1547~ PCI`/USgl/01075 Table B
COMPOUND
Rate (50 g/ha) 32 33 34 35 37 38 39 40 41 42 43 PREEMERGENCE
Barley 9 9 9 9 2 9 1 2 2 9 5 Barnyardgrass 9 9 9 9 7 9 5 7 5 9 9 Bedstraw 7 8 8 7 7 9 9 B 8 9 8 Blackgrass 9 9 9 8 5 9 4 9 8 9 8 Cheatgrass 9 9 10 9 8 9 8 9 8 9 8 Chickweed 10 - - 10 9 10 10 - 9 10 8 Cocklebur 9 9 9 - 6 8 9 - - 9 Corn 9 9 9 9 7 9 3 8 6 9 7 Cotton 9 9 9 9 3 9 8 8 0 8 5 Crabgrass 7 9 9 8 5 9 2 6 2 7 7 Giant fo~tail 7 6 8 9 5 8 6 7 2 9 8 Lambsquarters 10 10 - 10 9 9 10 10 9 10 9 Msrningglory 8 6 9 10 9 9 9 9 9 9 9 Nutsedge 9 10 9 10 7 10 9 0 9 10 10 Rape 10 9 9 9 9 10 9 9 9 9 8 Rice 10 9 10 9 8 10 8 7 8 9 9 Sorghum 9 9 9 9 9 10 8 7 0 9 9 Soybean 9 9 9 9 9 9 6 8 2 9 7 Sugar beet 9 8 8 9 9 9 9 9 9 9 9 Velvetloaf 9 9 9 9 8 9 7 9 7 9 8 Wheat 9 9 9 9 0 9 2 7 2 9 9 Wild buckwheat 8 8 8 8 5 6 1 5 5 9 8 Wild oat 9 9 9 9 1 9 1 2 7 2 7 wo 91/15478 PCr/US91/0l075 ~.~.
- 63 ~ ,r Table B
COMPOUND
Rate (l0g/ha)32 33 34 35 37 38 39 40 41 42 POSTEMERGENCE
" Barley 9 9 9 9 4 9 4 9 9 Barnyardgrass 8 l0 l0 9 9 9 9 9 8 l0 Bedstraw 6 7 7 8 l0 9 l0 l0 9 9 Blackgrass 9 9 9 8 8 9 7 9 9 l0 Cheatgrass 9 9 9 9 9 9 7 9 5 9 Chickweed 10 9 - l0 10 9 10 10 8 9 Cocklebur 10 9 l0 l0 l0 l0 l0 9 Corn 9 9 9 9 9 l0 l 9 4 9 Cotton g 9 9 9 9 9 9 9 9 g Crabgrass - - - 7 - 9 2 3 0 0 Giant fo~tail 8 7 l0 9 5 9 5 8 3 8 Lambsquarters 9 9 l0 l0 l0 9 10 9 9 9 Morningglory 6 3 8 9 l0 l0 9 9 l0 l0 Nutsedge 9 l0 l0 9 l0 l0 l0 9 9 8 Rape l0 9 9 9 9 9 9 l0 l0 9 Rice 9 9 l0 9 7 9 3 8 2 9 Sorghum 9 9 l0 9 9 l0 8 9 2 9 Soybean 9 9 9 9 9 9 9 9 8 9 Sugar beet l0 5 9 9 l0 9 9 9 l0 9 Velvetleaf 9 9 l0 9 l0 9 9 9 9 9 WheJt 9 9 9 9 3 9 2 7 l 9 Wiltl buckwheat - 7 l0 9 9 9 l0 9 9 7 Wild oat 9 9 l0 93 9 2 5 Z 2 '. -, ~
.
. . . ~

- , .. . .

WO 91/15478 PC~/US~l/`111075 ~''c ; ,.
2~ ~ ~Ç~9 64 Table B
COMPOUND
Rate (10g/ha) 3233 34 35 3738 39 4041 42 PREEMERGENCE
Barley 7 8 8 2 0 3 0 1 0 3 Barnyardgrass 3 4 9 7 3 7 0 3 2 7 Bedstraw 7 5 8 0 3 5 0 3 1 3 Blackgrass B 8 9 7 2 7 3 6 0 7 Cheatgrass 9 9 9 9 7 9 7 B 7 B
Chickweed 10 - - - 10 910 - 810 Cocklebur 7 9 7 - 0 8 7 0 - 6 Corn 9 9 9 8 1 7 0 2 0 0 Cotton 5 9 B 9 0 6 8 6 0 3 Crabgrass 2 6 6 3 1 9 0 2 0 0 Giant fo%tail 3 6 2 5 0 7 0 5 0 4 Lambsquarters 9 - 9 9 10 910 10 6 9 Morningglory 4 4 5 9 3 9 6 3 0 6 Nutsedge 5 9 9 9 0 10 7 3 0 0 Rape 9 9 9 9 8 9 2 2 3 9 Rice 9 9 9 9 4 9 6 2 3 6 Sorghum 1 9 8 9 0 8 0 1 0 3 Soybean 7 6 6 7 3 6 2 2 0 6 Sugar beet 8 7 7 8 8 8 9 7 8 8 Velvetleaf 7 2 9 7 7 8 5 5 2 3 Wheat 7 8 9 7 0 6 0 2 0 6 Wild buckwheat 5 6 8 3 2 3 0 0 2 2 Wild oat 5 8 9 6 0 4 0 3 4 0 wOsl/l~78 PCT/US91/01075 '~ 9 ~E~T C
~eeds of barley (Hordeum vulpare), barnyardgrAss (Ech~nnch]~ CL~=9~ blackgrass (Alopecurus myosu~Qides), chickweed (Stellaria medi~), cocklebur ( anthium pensylvani~um), corn (~
mays), cotton (Goss~Dium hirsutum), crabgrass (Digi,~Li~ spp.), downy brome (Bromu$ tecto~um), giant fo~tail (Setaria ,faberi), green fo~tail (Setaria viridis), jimsonweed (Datura s,~amoniu~), johnsongrass (Sor~hum haleDense), lambsquarters (Chenovodium ~l~m), morningglory (Ipomoea spp.), rape (~rasSica n~Y~), rice (QLXL~ ~ativa), sicklepod (Cassia ob~uaifQlia), soybean (Glycine m~), sugar beet (~ vulgaris), teaweed (~ sDinosa), velvetleaf (Abutilon theophrasti), wheat (Triticum aestivum), wild buckwheat (Polyaonu,m, conyolvulus), and wild oat (Avena fatua) and purple nutsedge (Cvperu_ rotundus) tubers were planted and treated preemergence with test chemicals dissolved in a non-phytoto~ic 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 (two to three leaf staqe) for postemergence treatments. Treated plants and controls were maintained in a greenhouse for appro~imately 24 days, after which all species were compared to controls and visually evaluated. Plant response ratings, summarized in ~able 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.

.
'' -WO9t/15478 PCT/VS91/01075 .~r~,~

Table C
COMPOUND
Rate (250 g/ha)4 10 POSTEMERGENCE
Sarley 7 Slackgrass 9 5 Chickweed 10 10 Cocklebur 10 10 Corn 8 2 Cotton 10 9 Crabgrass 7 3 Downy brome 7 5 Giant fo~tail 7 7 Green fo~tail 8 7 Jimsonweed 10 10 Johnsongrass 9 10 Lambsquarters 10 10 Morningglory 10 10 Nutsedge 10 4 Rape 10 10 Rice Dry Seed 10 9 Sicklepod 10 8 Soybean 9 10 Sugar beet 10 10 Toaweed 9 7 Vel~etleaf 10 10 Wheat 8 3 Wild buckwheat 9 10 Wild oat 9 2 Barnyardgrass 10 9 :
''' .

. WO 91/15478 PCI/US91/01075 ., .: ., Table C
COMPOUND
Rate (250 g/ha) 4 10 PREEMERGENCE
Barley 7 ~lackgrass 9 Chickweed 7 7 Cocklebur 10 6 Corn 9 o Cotton 7 4 Crabgrass 9 10 Downy brome 9 6 Giant fo~tail8 7 Green fo~tail9 7 Jimsonweed 9 B
Johnsongrass 9 B
Lambsquarters10 Morningglory 9 B
Nutsedge 9 0 Rape 10 9 Rice Dry Seed10 9 Sicklepod 9 5 Soybean B 3 8ugar beet 9 9 ~eaweed B 6 Velvetleaf 9 10 Wheat 9 Wild buckwheat 9 7 Wild oat 8 Barnyardgrass10 6 .

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:

wos~ 4~8 PCT/US91/01075 TEST_~
The compounds evaluated in thi~ test were formulated in a non-phyto~ic 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 appro~imately 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 vulaare), bedstraw (Galium aDarine), blackgrass (Alopecurus myosuroides), chickweed (Stellaria media), corn (~Q~ m~Y~), cotton (Gossy~ium hirsutum), crabgrass (Diaitaria sanguinalis), downy brome (~LQm~ tectorum), giant fo~tail (Setaria f~lii), lambsquarters (Chenopodium ~lk~m), morningglory (I~omoea hederacea), pigweed (Ama~anthusretrofle~us)~
rape (9rassica n~), ryegrass (~olium multiflp~u~m.), sor~hum (Sor~hum bicolor), soybean (Glyci~ ma~), speedwell (YSL9DUS~ ~ersica), sugar beet (~Q~
vulaaris), velvetleaf (~k~ theoDhras~j), wheat (Triticum aestivum), wild buckwheat (polyaonum convolvulus), and wild oat (Avena 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 WO91/1~78 PCT/US91/01075 (Echinochloa ~L~-9a~ rice (QLY~ sa~iva)~ and umbrella sedge (~Y~L~ diffnrmis).
All plant species were grown using normal greenhouse practices. Visual evaluations of injury e~pres6ed on treated plants, when compared to untreated controls, were recorded approYimately fourteen to twenty-one days after application of the test compound. Plant response ratings, summarized in Table D, were recorded on a 0 to 10 scale where 0 is no injury and 10 is complete control. A dash (-) response means no test result.

wo9l/ls478 PCT/US91/~1075 2,., ,.~ 9 Table D
COMPOUND
Rate (62 g/ha) 32 35 40 41 42 43 POSTEMERGENCE
Barley Igri 9 l0 l0 5 l0 6 Bedstrawl0 l0 l0 l0 l0 l0 Blackgrass9 l0 l0 l0 lO l0 Chickweedl0 l0 l0 l0 l0 l0 Cornl0 l0 l0 9 lO B
Cottonl0 l0 lC l0 l0 l0 Crabgrass7 l0 6 0 3 4 Downy brome 9 lO 9 6 l0 8 Duck salad- - - 9 9 Giant fostail l0 l0 l0 7 l0 9 Lambsquarters l0 l0 l0 l0 l0 l0 Morningglory l0 l0 l0 l0 l0 l0 Pigweedl0 l0 l0 l0 l0 l0 Rape10 ln 10 10 10 10 Ryegrassl0 l0 l0 3 5 7 Sorghuml0 l0 l0 7 l0 l0 Soybeanl0 l0 l0 7 l0 9 Speedwell9 l0 l0 l0 8 9 Sugar beetl0 l0 l0 l0 l0 l0 Volvetleafl0 l0 l0 l0 9 l0 Wheat9 9 9 3 9 7 Wild buckwheat l0 l0 l0 l0 9 B
Wild oat 9 9 6 S 4 7 ~arnyardgrass 9 l0 9 9 l0 9 ~ice Japonica 8 8 8 8 8 9 Vmbrella sedge l0 l0 9 9 9 9 `
.
`~

.

Table D
COMPOUND
Rate (62 g/ha) 32 35 40 41 42 43 PREEMERGENCE
Barley Igri 9 5 4 2 9 2 Bedstraw9 9 l0 l0 l0 l0 Blackgrass9 7 9 7 9 l0 Chickweedl0 - l0 9 9 9 Corn8 l0 2 3 7 3 Cotton6 9 9 l0 l0 7 Crabgrass8 l0 7 8 5 7 Downy brome l0 7 7 7 l0 7 Giant fostail 7 9 4 6 7 7 Lambsquarters l0 - l0 9 l0 l0 Morningglory B 8 l0 l0 9 Pigweedl0 l0 l0 9 l0 9 Rapel0 g l0 l0 9 l0 Ryegrassl0 l0 6 6 7 8 Sorghum9 l0 9 7 l0 9 Soybean7 9 7 0 9 4 Speedwelll0 9 l0 9 l0 9 Sugar beetl0 9 9 l0 l0 l0 Velvetloaf8 9 9 B 9 9 Wheat9 7 4 2 9 4 Wild buckwheat 9 8 9 8 9 9 Wild oat6 5 5 3 3 3 ~y ~

O91~1~78 PCT/US91/0107 ,~ 9 f~

Table D
COMPOUND
Rate (31 g/ha)32 33 34 35 37 38 39 40 41 42 43 POSTEMERGENCE
Barley Igri 9 9 9 l0 6 l0 4 9 4 9 5 Bedstrawl0 l0 l0 l0 l0 l0 l0 l0 l0 l0 l0 Blackgrass 9 9 9 l0 l0 l0 9 l0 9 l0 l0 Chickweedl0 l0 l0 l0 l0 l0 l0 l0 l0 l0 l0 Corn . l0 l0 l0 l0 8 l0 7 l0 8 l0 7 Cotton l0 l0 l0 l0 l0 l0 l0 l0 l0 l0 9 Crabgrass 6 7 l0 l0 0 8 0 5 0 0 3 Downy brome 8 l0 l0 l0 5 l0 4 9 5 l0 7 Duck salad - - - - - - - - 7 8 Giant fo~tail 8 l0 l0 l0 6 l0 6 l0 5 7 8 Lambsquartersl0 l0 l0 l0 l0 l0 - l0 l0 l0 l0 Morninggloryl0 8 8 l0 l0 l0 l0 l0 l0 l0 l0 Pigweed l0 l0 l0 l0 l0 l0 0 l0 8 l0 9 Rape l0 l0 l0 l0 l0 l0 l0 l0 l0 l0 l0 Ryegrass 9 l0 l0 l0 0 l0 4 l0 2 4 7 Sorghum l0 l0 l0 l0 l0 l0 7 l0 6 l0 l0 Soybean l0 l0 l0 l0 l0 l0 l0 l0 7 l0 9 Speedwell 9 8 B l0 5 8 9 9 l0 8 8 Sugar beetl0 l0 l0 l0 l0 l0 l0 l0 l0 l0 l0 Velvetleaf l0 l0 l0 l0 8 l0 l0 l0 l0 9 l0 Wheat 9 9 9 9 4 9 2 9 0 8 7 Wild buckwheat l0 l0 l0 l0 l0 l0 9 l0 l0 9 7 Wild oat8 9 l0 7 3 9 4 5 4 4 6 Barnyardgrass 9 8 9 9 8 9 7 9 8 9 9 Rice Japonica 8 8 9 8 7 9 8 8 8 8 9 Umbrella sedge l0 9 l0 l0 9 9 9 9 9 9 9 WO 91/15478 PCr/US91/01075 ,,.
.,, ,,-, ~, . .
81 2 ~ , ~ a J9 Table D
COMPOUND
Rate (31g/ha) 32 33 34 35 37 38 39 40 41 42 43 PREEME~GENCE
Barley ~gri 8 3 7 4 3 4 0 2 0 7 2 Bedstraw 8 9 10 9 10 891091010 Blackgrass 9 10 869879699 Chickweed 10 10 10 - 10 9 8 10 9 9 7 Corn 5 891006 3 0 0 7 2 Cotton 6 7 B 9 7 8 3 769 5 Crabgrass 8 7 810 3 7 0 76 4 5 Downy brome 8 8 10 6484 5 6 9 5 Giant fo~tail 6 889 2 710 3 6 6 4 Lambsquarters 10 10 10- 10 10 9 10 9 10 9 Morningglory 8 6 77 6 3 6 10 9 9 3 Pigweed 10 9 910 88 7 10 9 9 9 Rape 10 9 9 81010101010910 Ryegrass 9 10 10 9 4 5 5 4 6 6 5 Sorghum 891010 5 10 7 9 4 7 9 Soybean 67 2 7 0 60609 4 Speedwell 10 10 10 89101010999 Sugar beet 9 9 10 9 10 9 9 9 10 10 9 Velvetleaf 8 9 7 9 8 8 7 8 B 8 8 Wheat 66660 3 0 3 1 5 2 Wild buckwheat 9 9 8 8 8 9 8 8 7 9 9 W~ld oat 4 4 5 4 0 0 0 3 2 0 0 ...
.

WO 91/15478 PcltlJS~l/01075 Table D
COMPOUND
Rate (16g/ha) 32 33 34 35 37 38 39 40 41 42 43 POSTEMERGENCE
Barley Igri 8 9 9 10 5 9 4 8 3 9 4 Bedstraw 10 10 l0 10 10 10 10 10 10 10 9 Blackgrass 9 9 9 10 10 10 B 9 9 10 10 Chickweed 10 9 10 10 10 10 10 10 10 10 7 Corn l0 10 10 10 8 lO 6 10 6 10 6 Cotton 9 10 10 10 10 lO 10 lO 10 10 9 Crabgrass 5 6 9 9 0 7 0 4 0 0 0 Downy brome 7 9 9 B 4 10 4 5 4 10 6 Duck salad - - - - - - - - l 7 -Giant fo~tail 7 9 10 10 6 10 5 10 3 6 8 Lambsquarters 10 10 10 10 10 10 10 10 10 10 9 Morningglory 10 7 7 10 10 10 lO 10 10 10 9 Pigweed 10 9 10 10 7 9 0 10 7 5 R
Rcpe 10 10 10 10 10 10 10 10 10 10 10 Ryegrass 9 10 10 10 0 10 4 9 O 4 6 Sorghum 10 10 10 10 10 10 6 10 6 10 10 Soybean 10 10 10 10 10 10 10 10 7 10 9 Speedwell 8 8 8 9 5 8 9 8 10 7 7 Sugar beet 10 10 10 10 10 10 10 10 10 10 8 Volvetleaf 10 10 10 10 7 10 7 10 10 5 9 Wheat 6 9 9 4 4 9 O 7 O 8 7 Wild buckwheat 10 lO 9 10 10 10 8 10 10 9 6 Wild oat 4 8 9 5 2 9 4 4 4 4 5 Barnyardgrass 8 8 9 9 5 9 5 7 6 9 8 Rice Japonica 8 B 8 8 7 8 7 8 6 8 8 Umbrella sedge 9 9 10 9 9 9 5 9 9 9 9 ' . , :
. : ~
. ~ : - ~ ' ' ', ' .

~ wosl/l~78 PCT/US91/0107~

Table D
COMPOUND
Rate (l6 g/ha) 32333435373839404l 4243 PREEMERGENCE
9arley Igri 7363020 l O 6 l 9edstraw 89 lO 9 lO a 999 lo lo Blackgrass 98766758599 Chickweed 9 lO lO - lO 989894 Corn 48240020020 Cotton 67877725 - 95 Crabgrass 677 lO 2506633 Downy bro~e 87840334592 Giant fo~tail 58780623644 Lambsquarters lO lO lO - 9988999 Morningglory 6537632 lO 792 Pigweed 999 lO 8 B 7 lO 998 Rape lO 9989989 lO 9 lO
Ryegrass 9 lO lO 904 ~ 4365 Sorghum 396 lO 2 lO 43449 Soybean 66260305072 Speedwell lO 9 lO 88899899 Sugar beet 99999998 lO lO 9 Velvetleaf 78788777777 Whoat 6443000 l O 50 W~ld buckwheat 8877 B 977798 Wild oat 03330000000 WO 91/15478 PCl/US91/01075 Table D
COMPOUND
Rate (8 g/ha) 32 33 3435 37 38 39 40 41 42 43 POSTEMERGENCE
Barley Igri B 8 9 9 4 9 3 7 0 9 3 Bedstraw l0 l0 l0 l0l0 l0 l0 l0 l0 l0 8 Blackgrass 9 9 8 l0 7 l0 6 9 9 l0 9 Chickweed 9 9 l0 l0l0 l0 l0 l0 l0 l0 7 Corn l0 8 l0 l0 7 9 2 l0 2 l0 5 Cotton 9 9 l0 l0l0 l0 lO l0 l0 l0 9 Crabgrass O 5 8 7 0 6 0 3 0 0 0 Downy brome 5 6 9 8 4 9 3 4 3 l0 4 Duck salad ~ - - 0 0 -Giant fostail 6 7 l0 9 5 l0 3 l0 0 4 7 Lambsquarters l0 8 l0 9l0 l0 l0 l0 l0 l0 8 Morningglory 8 6 7 8l0 l0 l0 l0 lO l0 7 Pigweed l0 8 l0 9 7 7 0 l0 6 4 8 Rape ln to 10 l0l0 l0 l0 l0 l0 l0 l0 Ryegrass 6 9 l0 l0 0 9 3 7 0 2 5 Sorghum 7 l0 l0 l0l0 l0 6 lO 5 9 l0 Soybean l0 l0 l0 9l0 l0 l0 l0 7 l0 9 Speedwell 8 7 8 9 4 8 9 - l0 6 7 Sugar beet l0 9 l0 l0l0 l0 l0 l0 l0 l0 8 Velvetleaf l0 l0 l0 l0 7 l0 7 l0 l0 5 9 Wheat 5 6 9 4 0 8 O 5 0 7 6 Wild buckwheat l0 8 9 9 9 l0 8 l0 9 9 6 Wild oat 4 6 9 3 2 8 3 0 2 2 3 Barnyardgrass 7 7 9 9 4 7 l 6 4 6 8 Rice Japonica 8 8 8 8 6 8 l 8 l 6 8 IJmbrella sedge 9 9 9 9 6 9 4 9 7 6 9 .: - .
:~

: . - . .

, WO91/1W78 PCT/US91/01075 ~,- .
~, ~ ... ~ b 9 Table D
COMPOUND
Rate (B g/ha) 32 33 34 35 37 3B 39 40 41 42 43 PREEMERGENCE
8arley Igri 2 0 3 0 0 0 0 0 0 5 0 Bedstraw - 9 9 8 7 6 7 7 7 9 9 Blackgrass 8 8 7 5 4 6 4 7 4 9 6 Chickweed 9 l0 l0 - l0 9 7 9 5 9 4 Corn 0 7 0 2 0 0 0 0 0 0 0 Cotton 5 7 7 7 4 6 2 4 4 9 4 Crabgrass 4 4 6 8 0 3 0 6 6 3 2 Downy brome 6 6 8 3 0 0 0 3 3 5 2 Giant fo~tail 5 3 2 8 0 4 0 3 5 3 2 Lambsquarters 9 9 9 - 6 7 8 8 7 8 8 Morningglory 5 4 3 7 3 2 0 9 4 8 0 Pigweed 9 8 9 l0 7 7 7 l0 8 9 7 Rape 9 9 9 8 7 8 5 7 9 9 7 Ryegrass 4 8 l0 7 0 2 2 2 2 4 0 Sorghum 0 9 4 l0 0 4 2 0 3 3 7 Soybean 4 4 0 5 0 0 0 - 0 6 0 Speedwell 8 9 l0 8 8 7 - 8 8 8 8 Sugar beet 9 9 9 8 8 8 7 8 9 l0 9 Velvetleaf 6 8 7 8 4 6 3 7 7 7 7 Wheat 3 3 4 Wild buckwheat 7 B 7 7 7 8 6 7 7 8 7 Wil~ oat 0 2 2 0 0 0 0 0 0 0 0 .

wo 91/15478 pcr/us91/oto75 ~'' ~able D
COMPOUND
Rate (4 g/ha) 32 3334 35 37 3B 39 40 41 42 43 POSTEMERGENCE
Elarley Igri 6 7 7 6 4 8 2 5 O 7 0 Bedstraw 9 B 10 1010 10 10 10 10 10 7 ~lackgrass 9 8 8 9 6 9 5 9 O 10 8 Chickweed 9 8 10 1010 10 10 10 10 10 7 Corn 10 7 7 9 3 8 2 10 O 10 4 Cotton 9 8 10 1010 10 9 9 10 9 8 Crabgrass O 4 6 5 O 4 O 2 O O O
Downy brome 3 4 8 O 2 4 O 4 O 9 3 Duck salad - - - - - - - - O O -Giant fostail 5 6 10 8 3 7 3 6 O 2 4 Lambsquarters 10 8 10 8 9 10 10 10 9 10 7 Morningglory 6 4 6 710 10 10 10 10 10 3 Pigweed 7 8 10 9 7 7 O 10 5 4 4 Rape 10 10 10 10 9 10 10 10 10 10 10 Ryegrass 5 9 9 10 O 7 O 5 O O 3 Sorghum 7 9 10 10 7 10 6 10 3 8 10 Soybean 10 10 10 910 10 10 10 7 10 9 Speedwell 8 7 7 8 3 8 7 6 9 5 5 Sugar beet 9 8 10 1010 10 10 10 10 10 8 Vel~etleaf 10 10 9 10 7 10 6 10 10 2 9 Wheat 4 4 7 5 3 7 4 Wild buckwheat 9 8 9 7 9 10 - 8 9 7 6 Wild oat 2 4 6 O O 5 2 O O O O
18arnyardgrass 4 5 8 8 O 6 O 2 2 5 5 Rice Japonica 8 8 8 8 2 8 O 7 O O 7 Umbrella sedge 9 8 9 9 3 9 1 9 3 5 9 ,. ~ ' .:

WO s1/15478 PCr/U~91/0107~

2~7~S~9 Table D
COMPOUND
Rate (4 g/ha)32 33 34 35 37 38 39 40 41 42 43 PREEMERGENCE
Barley Igri 00 0 0 0 0 0 0 0 4 0 Bedstraw 88 8 8 6 6 5 7 6 9 9 Blackgrass 77 6 4 3 3 3 5 2 8 0 Chickweed 4l0 l0 - 9 8 7 8 5 9 0 Corn 06 0 2 0 0 0 0 0 0 0 Cotton 37 5 6 2 4 2 3 4 8 3 Crabgrass 44 4 7 0 2 0 3 3 3 2 Downy brome 64 7 3 0 0 0 3 2 3 0 Giant fo~tail 33 0 6 0 3 0 0 4 0 0 Lambsquarters 89 9 - 6 - 6 8 7 7 8 Morningglory 42 2 4 2 0 0 4 0 7 0 Pigweed 98 8 l0 7 5 4 8 7 7 7 Rape 98 8 8 7 8 3 7 7 9 3 Ryegrass 26 5 7 0 0 0 0 2 0 0 Sorghum 09 4 7 0 2 0 0 3 0 4 Soybean 42 0 2 0 0 0 3 0 6 0 Speedwell 89 9 8 5 - 9 8 8 8 6 Sugar beet - 8 8 8 8 8 7 7 7 9 8 Velvetleaf 67 6 7 2 5 2 5 6 6 5 Wheat Wild buckwheat 78 7 7 7 8 5 7 4 8 4 Wild oat , WO91/1~78 PCT/US91/01075 27 ~- . 88 Table D
COMPOUND
Rate (2 g/ha)33 34 37 38 39 POSTEMERGENCE
Barley Igri 5 7 3 5 2 Bedstraw 8 l0 l0 8 B
Blackgrass 7 7 6 8 4 Chickweed 6 9 l0 l0 8 Corn 7 7 o 7 o Cotton 5 8 l0 8 6 Crabgrass 3 4 0 0 0 Downy brome 2 6 0 3 0 Giant fostail 5 l0 3 5 2 Lambsquarters 7 8 8 l0 7 Morningglory2 4 l0 l0 l0 Pigweed6 l0 0 3 0 Rapel0 l0 8 l0 l0 ~yes-ass6 8 0 4 0 Sorghum7 9 7 l0 6 8eybeanl0 9 l0 l0 l0 Speedwell 5 7 3 6 6 8ugar beet 8 l0 l0 9 l0 Velvetlea 7 7 7 7 6 Wheat 4 6 0 4 0 Wil~ buckwheat 3 9 7 9 7 Wild oat 3 4 0 4 0 Barnyardgrass 0 - 0 3 0 Rice Japonica 7 7 l 7 0 Umbrella sedge 7 9 3 9 0 ~, ` ' ' ' , ., Table D
COMPOUND
Rate (2 g/ha)33 34 37 38 39 PREEMERGENCE
Barley Igri0 0 0 0 0 Bedstraw 8 8 5 5 4 Blackgrass 6 5 2 3 3 Chickweed l0 l0 9 5 6 Corn 4 0 0 0 0 Cotton 6 5 0 2 0 Crabgrass 2 0 0 0 0 Downy brome 3 6 0 0 0 Giant fo~tail 2 0 0 0 0 Lambsquarters 9 9 5 6 5 Morningglory 0 0 0 0 0 Pigweed 7 7 6 5 4 Rape 8 8 6 5 0 Ryegrass 4 7 0 0 0 Sorghum 5 2 0 0 0 Soybean 0 0 0 0 0 Speedwell 9 8 - 4 7 Sugar beet 8 8 6 7 6 Velvetleaf 6 6 0 3 0 Wheat Wild buckwheat 7 7 7 6 4 Wild oat 0 0 0 0 0 . _. ; ' . ' ' ' WOgl/1~78 PCT/US91/01075 r~

~E~
~eeds of barnyardgrass (Eshin~shlQ~
,c"rus-galli), cocklebur (X~n~hiYm ~ensylvanicum), corn ~ m~Y~) (soil surface e~posed and 60il surface covered with perlite), crabgrass (Diqitaria spp.), fall panicum (Panicum dichotomiflorum), giant fostail (Setaria faberii), green fostail (Setaria viridis), ivyleaf morningglory (Ipomoea hederacea), jimsonweed (Datura ~tL~mQnium), johnsongrass (~QLgh~_ halepense), ladysthumb smartweed (Polyaonum per~icaria), lambsquarters (Chenopodium ~lk~_), redroot pigweed (Amarsnthus retrofle~us), sorghum (,SQ~hum ~ic,olQ,~,), 60ybean (Glycine ma~), and velvetleaf (Abutilon theophrasti) and purple nutsedge (Cv~erus rotundus) tubers were planted and treated preemergence with test chemicals dissolYed in a non-phytotosic solvent. These crop and weed species were also treated with postemergence applications of test compounds. Plants ranged in height from two to twenty-five cm for postemergence treatments.
Treated plants and controls were maintained in a greenhouse for appro~imately 24 days, after which all ~pecies were compared to controls and visually evJluated. The ratings, ~ummarized in Table E, are based on a scale of 0 to lO where 0 is no effect and 10 ifi complete control. A dash (-) response means no test result.

. .

WO 91/15478 2~ wn'~9 PCI/IJS91/01075 l, .

gl Table E
COMPOUND
Rate (500 g/ha) 5 PREEMERGENCE
Barnyardgrass 10 Cocklebur 10 Corn 6 Crabgrass 10 Fall panicum 10 Giant fostail 10 Green fostail 10 Ivlf mrninglory 10 Jimsonweed 10 Johnsongrass 10 Ladysthmb smtwd 10 Lambsquarters 10 Purple nutsedge 10 Redr~ot pigweed 10 Sorghum 10 Soybean 10 Velvetleaf 10 Table E
COMPOUND
Rate (250 g/ha) 5 7 8 9 l0 PREEMERGENCE
~arnyardgrassl0 l0 l0 l0 7 Cocklebur l0 9 6 8 2 Corn 3 9 4 6 0 Crabgrass 9 9 6 8 2 Fall panicum l0 l0 7 9 4 Giant fo~tail l0 l0 l0 9 4 Green fo~tail l0 l0 9 9 3 Ivlf mrningloryl0 9 9 9 3 Jimsonweed l0 4 6 9 2 Johnsongrass l0 l0 l0 l0 6 Ladysthmb smtwdl0 - - l0 9 Lambsquarters l0 - - - -Purple nutsedgel0 l0 l0 l0 4 Redroot pigweedl0 l0 l0 l0 l0 Sorghum l0 l0 l0 l0 9 Soybean . l0 - - 8 7 Velvetleaf l0 8 8 6 4 - . ~

, WO91/1~78 ~ PCT/US91/01~75 . , ~ f . , -, Table E
COMPOUND
Rate (125 g/ha) 5 7 8 9 l0 POSTEMERGENCE
Barnyardgrass l0 l0 l0 l0 9 Cockleburl0 l0 l0 l0 l0 Corn7 l0 2 6 0 Crabgrassl0 l0 7 2 0 Fall panicuml0 l0 9 2 0 Giant fo~tail l0 l0 8 4 2 Green fo~tail l0 l0 9 4 4 Ivlf mrninglory l0 l0 l0 l0 l0 Jimsonweedl0 l0 l0 l0 l0 Johnsongrassl0 l0 l0 l0 l0 Ladysthmb smtwd l0 - - l0 6 Lambsquarters 9 l0 9 7 6 Perlite corn5 6 2 4 0 Purple nutsedge .10 10 l0 l0 4 Redroot pigweed l0 l0 l0 l0 l0 Sorghuml0 l0 l0 l0 l0 Soybeanl0 l0 l0 l0 l0 Velvetleafl0 l0 l0 l0 l0 -W091/1~7R PCT/US91/01075 2~ 9 94 ~able E
COMPOUND
Rate ~125 g/ha) 5 7 8 9 l0 PREEMERGENCE
Barnyardgrassl0 l0 l0 9 4 Cocklebur 8 7 3 6 0 Corn 2 6 2 4 0 Crabgrass 7 7 5 5 o Fall panicuml0 7 6 6 2 Giant fo~taill0 9 9 7 0 Green fo~taill0 8 8 6 0 Ivlf mrninglory 8 7 7 8 2 Jimsonweed 9 2 3 7 0 Johnsongrassl0 l0 l0 9 5 Ladysthmb smtwd l0 - - l0 6 Lambsquartersl0 - - - -Purple nutsedge l0 l0 9 9 0 Redroot pigweed l0 l0 l0 l0 9 Sorghum l0 l0 l0 9 7 Soybean 9 - - 6 4 Velvetleaf 9 6 6 3 2 ' ' :.

.

WO91/1~78 PCT/US91/01075 g5 Table E
COMPOUND
Rate (64 g/ha) 5 7 8 9 10 24 POSTEMERGENCE
Barnyardgrass 10 10 10 10 B 9 Coc~lebur10 10 10 10 10 10 Corn 3 9 0 3 0 0 Crabgrass10 9 S 0 0 0 Fall panicum 10 10 7 0 0 0 Giant fo~tail 10 9 7 2 0 0 Green fo~tail 10 10 8 2 2 0 lvlf mrninglory 10 10 9 10 10 10 Jimsonweed10 7 10 9 10 9 Johnsongrass 10 10 10 10 7 7 Ladysthmb smtwd 10 - - 10 5 9 Lambsquarters 8 9 8 6 4 7 Perlite corn 2 4 0 2 0 0 Purple nutsedge 10 10 10 10 2 10 Redroot pigweed 8 10 10 10 10 10 Sorghum10 10 10 10 9 8 Soybean10 10 10 10 10 10 Velvetleaf10 10 10 10 10 10 ~ ~ .

Wo91/15478 PCT/US91/01075 2~

Table E
COMPOUND
Rate ~64 g/ha) 5 7 8 9 10 PREEMERGENCE
Barnyardgrass 10 10 8 7 2 Cocklebur5 7 0 2 0 Corn0 4 0 3 0 Crabgrass5 5 3 3 0 Fall panicum10 6 4 3 0 Giant fo~tail 9 6 6 4 0 Green fo~tail 10 5 4 3 0 lvlf mrninglory 6 6 5 5 0 Jimsonweed6 0 0 4 0 Johnsongrass10 10 10 7 3 Ladysthmb smtwd 9 - - 8 4 Lambsquarters 10 Purple nutsedge 10 8 8 7 0 Redroot pigweed 10 10 10 10 8 Sorghum10 10 10 6 5 Soybean7 - - 4 2 Velvetleaf6 5 2 2 0 WO91/1~78 PCT/US91/01075 .~

Tsble E
COMPOUND
Rate (32 g/ha) 5 7 8 9 l0 24 POSTEMERGENCE
Parnyardgrass l0 l0 l0 l0 6 6 Cocklebur l0 l0 l0 l0 l0 l0 Corn 0 6 0 0 0 0 Crabgrass 6 8 3 0 0 0 Fall panicum l0 8 4 0 0 0 Giant fo~tail l0 9 5 0 0 0 Green fo~tail l0 l0 8 0 0 0 I~lf mrninglory l0 l0 8 9 l0 l0 Jimsonweed 8 6 8 9 l0 8 Johnsongrsss l0 l0 l0 l0 6 5 Ladysthmb smtwd 9 - - 9 5 9 Lambsquarters 7 7 7 4 2 6 Perlite corn 0 3 0 0 0 0 Pui~p;e nutsedge l0 l0 9 9 2 l0 Redroot pigweed 7 l0 l0 l0 l0 9 Sorghum l0 l0 l0 l0 8 5 Soybean l0 l0 l0 l0 l0 l0 Vel~etleaf l0 l0 9 9 9 l0 ~ , '~ .

, . . . . .

W O 91/15478 P ~ /US91/01075 2~ ,.~, .~,~ ~

Table E
COMPOUND
Rate (32 g/ha) 5 7 8 9 10 PREEMERGENCE
Barnyardgrass 8 6 4 3 0 Cocklebur 2 4 0 0 0 Corn 0 2 0 0 0 Crabgrass 3 2 0 0 0 Fall panicum 7 3 2 0 0 Giant fostail 8 5 2 0 0 Green fo~tail 8 4 0 0 0 Ivlf mrninglory 3 3 2 2 0 Jimsonweed 2 0 0 2 0 Johnsongrass 9 7 6 3 0 Ladysthmb smtwd 8 - - 3 2 Lambsquarters 9 Purple nutsedge 9 7 3 3 0 Redroot pigweed 10 9 8 6 6 Sorghum 10 8 5 3 2 Soybean 5 - - 0 0 Velvetleaf 2 3 0 0 0 W091/15478 ~9 PCT/US91/nlO7~

... 99 ~able E
COMPOUND
Rate (16 g/ha) 5 7 8 9 10 24 POSTEMERGENCE
Barnyardgrass 10 10 8 9 4 2 Cocklebur 10 10 9 10 6 10 CornO 4 0 0 0 O
Crabgrass4 6 O 0 0 0 Fall panicum8 6 3 O 0 0 Giant fo~tail 9 8 3 0 0 0 Green fostail 9 9 7 0 0 0 Ivlf mrninglory 10 9 7 9 9 10 Jimsonweed7 4 6 7 9 8 Johnsongrass10 10 9 9 3 2 Ladysthmb smtwd 8 - - 8 3 7 Lambsquarters 6 6 5 2 0 S
Perlite corn0 2 O 0 O O
Purple nutsedge 10 10 6 8 O 7 Redroot pigweed 6 10 9 9 10 7 Sorghum10 10 10 10 5 3 Soybean10 10 9 10 10 10 Velvetleaf 10 10 6 7 6 10 ~,~ 100 Table E
COMPOUND
Rate (16 g/ha) 5 9 PREEMERGENCE
Barnyardgrass 6 0 Cocklebur 0 0 Corn 0 0 Crabgrass 0 0 Fall panicum 4 0 Giant foztail 4 0 Green foztail 4 0 Ivlf mrninglory 2 0 Jimsonweed 0 0 Johnsongrass 6 0 Ladysthmb smtwd 6 0 Lambsquarters 5 Purple nutsedge 7 0 Re~root pigweed 6 3 Sorghum 7 0 Soybean 2 0 Velvetleaf 0 0 WO 91 J 15478 PCr/US9 1/1)1075 ~, .

Table E
COMPOUND
Rate (8 g/ha) 5 7 8 9 10 24 POSTEMERGENCE
Barnyardgrass 10 10 6 7 2 0 Cocklebur8 8 5 8 7 9 CornO 2 0 0 0 0 Crabgrass2 3 O 0 0 O
Fall panicum6 3 0 0 0 0 Giant fo~tail 8 5 2 0 O 0 Green fo~tail 9 8 5 0 0 0 Ivlf mrninglory 9 8 3 8 7 9 Jimsonweed7 2 3 4 7 7 Johnsongrass9 10 8 6 2 O
Ladysthmb smtwd 7 - - 5 2 5 Lambsquarters 3 4 2 0 0 4 Perlite corn0 0 0 0 0 0 Purple nutsedge 10 9 4 5 0 4 Redroot pigweed 3 9 9 8 9 7 Sorghum10 10 9 6 3 0 Soybean10 10 7 10 6 10 Velvetleaf9 8 3 4 4 8 .

,,,,~, ,~.
~r ~ .~

Table E
COMPOUND
Rate (4 q/ha) 5 7 8 9 l0 24 POSTEMERGENCE
Barnyardgrass 9 7 2 3 0 0 Cocklebur 6 5 2 3 3 6 Corn 0 0 0 0 0 0 Crabgrass 0 0 0 0 0 0 Fall panicum 3 0 0 0 0 0 Giant fo~tail 5 3 0 0 0 0 Green fo~tail 7 6 3 0 0 0 Ivlf mrninglory 7 5 0 3 3 6 Jimsonweed 6 0 0 2 3 4 Johnsongrass 8 9 6 2 0 0 Ladysthmb smtwd 3 - - 2 0 2 Lambsquarters 0 2 0 0 0 2 Perlite corn 0 0 0 0 0 0 Purple nutsedge 8 6 2 2 0 2 Redroot pigweed 0 8 5 6 6 4 Sorghum 9 9 5 2 0 0 Soybean l0 l0 3 8 3 10 Velvetleaf 7 6 0 2 2 5 WO91/1s478 PCT/US91/0107~
2~ f ~. ``~

TES~_ F
Plastic pots were partially filled with ~ilt loam 80~ he soil was then 6aturated with water.
Indica an~ Japonica rice (Orvza E~L~g) seedlings at the 2.0 to 2.5 leaf stsge, seeds selected from barnyardgrass (~hin~hlQa crus-galli), bulrush (SciL~u5 mucronatus), duck salad (Heteranthera ~imosa), umbrella sedge (cy~erus diff~Lmi~) Jnd tubers selected from waterchestnut (Eleochraris 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.
lS Chemical treatments were formulated in a non-phytoto~ic solvent and applied directly to the paddy water. Treated plants and controls were maintained in a greenhouse for approsimately 21 days, after which all species were compared to controls and visuallv evaluated. Plant resp^nse ratings, summarized in Table F, 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.

~5 .
.. . . ..
- :-.: , . . .
. .

.: :

~,, J.,r~ g Table F
COMPOUND
Rste (64 g/ha) 27 PADDY
Barnyardgrass 6 Bu lrush 9 Duck salad 10 Indica rice 2 Japonica rice 4 Umbrella sedge 10 Waterchestnut 10 COMPOUND
Rate (32 g/ha) 11 17 27 PADDY
Barnyardgrass 8 5 6 Bu lrush 9 9 9 Duck salad10 10 10 Indica rice3 0 2 Japonica rice 4 4 4 Umbrella sedge 10 9 10 Waterchestnut - - 9 COMPOUND
Rate (16 g/ha) 11 17 22 23 27 PADDY
Barnyardgrass 7 4 10 7 4 Bulrush 8 9 8 9 7 Duck salad10 10 10 10 8 Indica rice3 0 9 4 2 Japonica rice 3 0 9 6 0 Umbrella sedge 10 9 10 10 9 Waterchestnut - - l0 8 9 .. . .

.

wo 91/15478 2~ Ç~3 PC~/US91/01075 f':, . .
. . , , , : . , Table ~
COMPOUND
Rate (8 g/ha) ll17 22 23 27 PADDY
Barnyardgrass6 0 9 5 4 Bulrush 7 8 8 6 6 Duck salad l0 4 l0 8 7 Indica rice 2 0 8 4 0 Japonica rice3 0 8 6 0 Umbrella sedge 9 9 10 8 7 Waterchestnut - - 6 2 3 COMPOUND
Rate (4 g/ha)ll17 22 23 27 PADDY
Barnyardgrass3 0 9 4 3 Bulrush 0 2 8 0 0 Duck salad 9 0 l0 3 0 Indica rice 0 0 6 2 0 Japonica rice0 0 7 4 0 Umbrella sedge 9 7 l0 6 5 Waterchestnut - - 4 2 3 COMPOUND
R~te (2 g/ha)ll 17 22 23 PADDY
Barnyardgrass3 0 7 2 Bulrush 0 0 2 0 Duck salad 7 0 9 2 Indica rice 0 0 4 0 Japonica rice0 0 7 4 Umbrella sedge 7 0 8 3 Waterchestnut - - 3 2 - , , WO91/1~78 PCT/US91/01075 2r ~ 3 ~
.`., ~ .~. " ~

Table F
COMPOUND
Rate (1 g/ha) 22 23 PADDY
Barnyardgrass 6 0 Bulrush 2 0 Duck salad 3 Indica rice 4 0 Japonica rice 6 4 Umbrella sedge g 2 Waterchestnut 2 2 .

' ' wos1/1~478 PCT/US91/01075 T~T G
Compounds evaluated in this test were formulated in a non-phytosic solvent and ~pplied to the 80il 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 mi~ture of sandy loam soil and greenhouse potting mi~ in a 60:40 ratio was used for the postemergence test. Test compounds were applied within appro~imately one day after planting seeds for the preemergence test. Plantings of these crops and weed species were adjusted to produce plsnts of appropriate size for the postemergence test. All plant species were grown using normal greenhouse practices. Crop and weed species include winter barley (,Ho~deum vula~re cv. 'Igri'), bedstraw (Galium apa~ine), blackgrass (Alo~ecur~
myosur~ide,s,), chickweed (Stella~ia m,e,~ downy brome (Bromus tec~Qr~), field violet (Vio~a arv,eDs~), green fo~tail (Setari~ viridi_), kochia (XQ~hia ~sQL~Li~), lambsquarters (che-nQ2Qdium ~l~m), Persian speedwell (verQnia Dersls~)~ rape (~55iS~
n~ cv. 'Jet Neuf'), ryegrass (LQli~m m~lLi~gm), sugar beet (~Q~ vulgar~ cv. 'USl'), sunflower ~Heli~n~hYs ~nn~Us cv. 'Russian Giant'), spring wheat (Triti~ym aestivum cv. 'ERA'), winter wheat (ILi~iL~
ae,stivum cv. 'Talent'), wild buckwheat (Polvaonum convolvulus), wild mustard (sina~is arvens~E), wild oat (Avena fa~), and wild radish (Raphan~
raDhanistrum). ~lackgrass and wild oat were treated postemergence at two growth stages. The first stage (l) was when the plants had two to three leaves. The second stage (2) was when the plants had wosl/ls478 PCT/US91/01075 appro~imately four leaves or in the initi~l stsges of tillering. Treated plants snd untreated controls were maint~ined in a ~reenhouse for appro~imately 21 to 28 dsys, ~fter which all tre~ted plants were compared to untreated controls and visually evaluated. Plant response rstings, summarized in Tsble G, sre based upon a 0 to 10 scale where 0 is no effect and 10 is complete control. A dash response (-) means no test result.

~. ` ' -.

Wosl/l5478 PCT/US91/01075 ,, Table G
COMPOUND
Rate (125 g/ha)37 39 POSTEMERGENCE
Bedstraw 10 10 ~lackgrass (1) 8 6 Blackgrass (2) 8 5 Chickweed 10 10 Downy brome 8 7 Field violet 10 7 Green fo~tail 6 4 Persn Speedwell4 8 Rape 10 10 Ryegrass 2 2 Sugar beet 10 10 Sunflower 10 10 Wheat (Spring) 3 3 Wheat (Winter) 2 3 Wild buckwheat10 9 Wild mustard 10 10 Wild oat (1) 2 5 Wild oat (2) 0 4 Wild radish 10 10 Winter !8arley 3 3 WO9l/15~78 PCT/US91/01075 ~.~
2 ., ~i.;

Table G
COMPOUND
Rate (125 g/ha) 37 39 PREEMERGENCE
E~edstraw 10 10 Blackgrass (1)2 0 Blackgrass (2)2 0 Chickweed 10 9 Downy brome 4 2 Field violet 10 7 Green fostail 2 2 Persn Speedwell 10 8 Rape 10 10 Ryegrass 4 3 Sugar beet 10 10 Sunflower 7 5 Wheat (Spring)3 2 Wheat (Winter)3 2 Wild buckwheat7 5 Wild mustard 10 10 Wild oat (1) 3 0 Wild oat (2) 2 0 Wild r~dish 10 9 Wlnter ~arley 4 2 WO91/15478 PCT/~S91/01075 ~ ~

Table G
COMPOUND
Rate (64 g/ha)34 35 37 39 POSTEMERGENCE
Pedstraw10 8 10 10 Plackgrass (1)4 8 6 4 81ackgrass (2)5 8 5 4 Chickweed10 10 10 10 Downy brome9 10 6 5 Field violet6 5 8 5 Green fo~tail10 9 5 Z
Rochia - 9 Lambsquarters10 8 Persn Speedwell 7 3 3 6 Rape10 10 10 10 Ryegrass10 10 0 0 Sugar beet10 10 10 10 Sunflower10 10 ln 10 Wheat (Spring)9 10 2 2 Wheat (Winter)9 10 1 2 Wild buckwheat10 9 9 8 Wild mustard10 10 10 10 W~ld oat (1)10 10 0 2 Wild oat (2)10 10 0 2 Wild radish10 10 10 10 Winter Barley10 10 2 2 W09l/15478 PCT/US91/01075 .5~9 Table G
COMPOUND
Rate (64 g/ha) 34 35 37 39 PREEMERGENCE
Bedstraw10 10 10 8 Blackgrass (1) 3 8 0 0 Blackgrass (2) 3 8 0 0 Chickweed10 10 10 8 Downy brome6 10 2 0 Field violet10 10 10 5 Green fo~tail 10 10 0 0 Kochia - 9 Lambsguarters - 10 Persn Speedwell 10 9 10 7 Rape10 10 10 10 Ryegr3ss7 10 2 0 Sugar beet10 10 10 10 Su.,.~o~trB 10 6 3 Wheat (Spring) 3 9 2 0 Wheat (Winter) 3 8 2 0 Wild buckwheat 4 8 5 3 Wild mustard10 10 10 10 Wild oat (1)4 6 0 0 Wild oat (2)4 6 0 0 W~ld radlsh9 10 8 7 Winter Barley 5 10 2 0 ', ' :

2~79r~r'9 Table G
COMPOUND
Rate (32 g/ha) 34 35 37 39 POSTEMERGENCE
E3edstraw 10 6 8 8 ~lackgrass (1) 3 6 4 2 Blackgrass (2) 4 6 4 2 Chickweed10 10 10 10 Downy brome8 10 3 3 Field violet5 3 6 3 Green fostail10 9 4 0 Rochia - 6 Lambsquarters10 6 Persn Speedwell 5 2 2 4 Rape 10 10 10 10 Ryegrass 10 10 0 0 Sugar beet10 10 10 10 Sunflower10 10 10 10 Wheat (Spring) 8 8 0 0 Wheat (Winter) 7 7 0 0 Wild buckwheat 8 7 6 6 Wild mustard10 10 10 10 W$1d oat (1)8 8 0 0 W$1d oat (2)8 8 0 0 Wild r~dish10 10 10 10 Winter Barley10 10 0 0 wosl/ls~78 PCT/US91/01075 Table G
COMPOUND
Rate (32 g/ha) 34 35 37 39 PREEMERGENCE
Bedstraw10 8 7 6 Blackgrass (1) 2 7 0 0 Blackgrass (2) 2 7 0 0 Chickweed10 10 9 5 Downy brome5 10 0 0 Field violet8 10 9 4 Green fo~tail10 10 0 0 Rochia - 8 Lambsquarters- 10 Persn Speedwell 10 8 8 5 Rape10 10 10 9 Ryegrass4 10 0 0 Sugar beet10 10 10 10 Sunflower6 ~ 2 Wheat (Spring) 2 7 0 0 Wheat (Winter) 1 6 0 0 Wild buckwheat 3 6 4 2 Wild mustard10 10 10 9 Wild oat (1)2 4 0 0 Wild oDt (2)2 5 0 0 Wild rodish7 10 7 4 Winter Parley4 10 0 0 -wo9l/ls478 PCT/US91/01075 Table G
COMPOUND
Rate (16 q~ha) 34 35 37 39 POSTEMERGENCE
~edstraw 8 4 6 5 ~lackgrass (1) 2 3 2 0 Blackgrass (2) 2 4 2 0 Chickweed 9 9 10 7 Downy brome6 8 0 0 Field violet4 2 3 2 Green fo~tail10 8 2 0 Kochia - 4 Lambsquarters9 3 - -Persn Speedwell 3 0 0 2 Rape 10 10 10 10 Ryegrass 10 8 0 0 Sugar beet9 9 10 10 Sunflower10 10 10 10 Wheat (Spring) 5 5 0 0 Wheat (Winter) 5 4 0 0 Wild buckwheat 7 3 4 5 Wild mustard10 10 10 10 Wild oat (1)7 7 0 0 Wild oat (2)6 7 0 0 Wild radish10 10 10 10 Winter ~arley10 9 0 0 WO91/15478 PCT~US91/01~75 ~J4 ~ ~ , ~ 5 ~

Table G
COMPOUND
Rate (16 g/ha)34 35 37 39 PREEMERGENCE
Bedstraw 8 6 5 4 Blackgrass (1)0 4 0 0 .
Blackgrass (2)0 5 0 0 Chickweed8 8 8 3 Downy brome4 8 0 C
Field violet5 10 7 2 Green fo~tail7 8 0 0 Kochia - 6 Lambsquarters- 10 - -Persn Speedwell7 7 6 3 Rape 10 10 8 7 Ryegrass 2 9 0 0 Sugar beet10 10 9 8 Sunflower4 7 3 0 Wheat (Spring)0 4 0 0 Wheat (Winter)0 4 0 0 Wild buckwheat2 5 2 0 Wild mustard10 10 9 8 Wild oat (1)0 2 0 0 Wild oat (2)0 2 0 0 Wild radish6 B 6 3 Winter ~arley2 B 0 0 : :

.

wo~l/ls47X PCT/US91/01075 Table G
COMPOUND
Rate (8 g/ha)34 35 37 39 POSTEMERGENCE
Bedstraw 5 2 4 2 Blackgrass (1)0 2 0 0 Blackgrass (2)0 2 0 0 Chickweed 7 8 10 4 Downy brome 4 4 0 0 Field ~iolet 2 0 0 0 Green fo~tail7 5 0 0 Kochia - 2 - -Lambsquarters 7 0 Persn Speedwell2 0 0 0 Rape 10 10 10 10 Ryegrass 10 6 0 0 Sugar beet 6 8 10 10 Sunflower 10 10 10 ln Wheat (Spring)3 3 0 0 Wheat (Winter)2 2 0 0 Wild buckwheat4 0 2 2 Wild mustard10 10 10 8 Wild oat (1) 5 4 0 0 Wild oat (2) 4 5 0 0 WilC r~ish 10 10 10 10 Winter Earley8 6 0 0 WO 91/15478 PCI /US9 l J01075 ~ ~9 ~18 Table G
COMPOUND
Rate (8 g/ha) 39 35 37 39 PREEMERGENCE
Bedstraw 6 5 3 2 Blackgrass (1) 0 2 0 0 Blackgrass (2) O 2 0 O
Chickweed 6 7 4 0 Downy brome 2 6 0 0 Field violet 3 9 4 O
Green fostail 4 6 0 0 Kochia - 5 - -Lambsquarters - 10 Persn Speedwell 5 6 3 O
Rape 7 10 6 6 Ryegrass 0 7 0 0 Sugar beet 8 9 7 6 Sunflo~er 3 6 0 0 Wheat (Spring) 0 3 0 0 Wheat (Winter) Q 2 0 0 Wild buckwheat 0 4 0 0 Wild mustard 8 9 7 6 Wild oat (1) 0 0 0 0 Wild oat (2) 0 0 Wild radish 4 7 4 0 Winter Barley 0 5 0 O

WO91/1~78 PCT/US91/01075 ~., 2~ ~"~,~
Ta~le G
COMPOUND
Rate (4 g/ha)34 35 37 39 POSTEMERGENCE
Bedstraw 3 0 2 0 Blackgrass (1) 0 0 0 0 Blackgrass (2) O O 0 0 Chickweed 5 5 10 2 Downy brome3 2 0 0 Field violet0 0 0 0 Green fo~tail6 4 0 0 Rochia - 0 Lambsquarters6 0 Persn Speedwell 0 0 0 0 Rape 10 10 10 10 Ryegrass 7 3 0 O
Sugar beet4 5 10 8 Sunflower10 10 10 10 Wheat (Spring) 0 2 0 0 Wheat (Winter) 0 0 0 0 Wild buckwheat 2 0 0 0 Wild mustard10 10 8 6 Wild oat (1)3 2 0 0 Wild oat (2)2 3 0 0 Wil~ radi~h9 10 10 10 Winter Barley6 3 0 0 WO9l/15478 PCT/US91/0107 Table G
COMPOUND
Rate (4 g/ha) 34 35 37 39 PREEMERGENCE
Bedstraw 3 4 2 0 Blackgrass (1) 0 0 0 0 Blackgrass (2) 0 0 0 0 Chickweed 4 4 2 0 Downy brome 0 3 0 0 Field violet 2 6 2 0 Green fostail 2 4 0 0 Kochia - 3 Lambsquarters - 7 Persn Speedwell 3 4 0 0 Rape 6 9 4 4 Ryegrass 0 3 0 Sugar beet 7 8 6 4 Sunflower o 5 o n Wheat (Spring) 0 0 0 0 Wheat (Winter) 0 0 0 0 Wild buckwheat 0 3 0 Wild mustard 4 8 5 3 Wild oat (1) 0 0 0 Wild oat ~2) 0 0 0 0 Wild radish 2 5 2 0 Winter Parley O 4 0 0 WO91/l5478 PCT/US91/01075 ~," , , 121 ~ ~9 Table G
COMPOUND
Rate (2 g/ha)34 35 POSTEMERGENCE
Bedstraw 2 0 Blackgrass (1)0 0 Blackgrass (2)0 0 Chickweed 4 2 Downy brome 2 0 Eield violet0 0 Green fo~tail3 2 ~ochia - 0 Lambsquarters5 0 Persn Speedwell 0 0 Rape 10 8 Ryegrass 5 2 Sugar beet 2 3 Sunflower 10 10 Wheat (Spring)0 0 Wheat (Winter)0 0 Wild buckwheat0 0 Wild mustard10 10 Wild oat (1)2 0 Wild oat (2)0 0 W$ld rodish 8 9 Winter ~arley4 2 WO9l/15478 PCT/US9l/01075 2r ~ f ~

Table G
COMPOVND
Rate (2 g/ha) 34 35 PREEMERGENCE
Bedstraw 2 3 ~lackgrass (1) 0 0 ~lackgrass (2) 0 0 Chickweed 2 2 Downy brome 0 0 Field violet 0 4 Green fo~tail 0 3 Xochia - 0 Lambsquarters - 4 Persn Speedwell2 2 Rape 4 6 Ryegrass 0 0 Sugar beet 6 6 Sunflower 0 3 Wheat (Spring) 0 0 Wheat (Winter) 0 0 Wild buckwheat 0 2 Wild mustard 2 6 Wild oat (1) 0 0 Wild oat (2) 0 Wild radish 0 3 Winter Darley 0 2 . . .
-: .. .. .. - : :

f ~ `

Table G
COMPOUND
Rate (1 g/ha) 34 POSTEMERGENCE
Bedstraw 0 Blackgrass (1) 0 Blackgrass (2) 0 Chickweed 2 Downy brome 0 Field violet 0 Green fo~tail 0 Lambsquarters 3 Persn Speedwell 0 Rape 8 Ryegrass 2 Sugar beet 0 Sunflower 10 Wheat (Spring) n Wheat (Winter) 0 Wild buckwheat 0 Wild mustard 10 Wild oat (1) 0 Wil~ o~t (2) 0 Wild radish 6 Wlnter Barley 2 - ~ - . .

2~ 9 ~

THble G
COMPOUND
Rate (1 ~/ha) 34 PREEMERGENCE
Bedstraw o Plackgrass (1) 0 Blackgrass (2) 0 Chickweed 0 Downy brome 0 Field violet 0 Green fo~tail 0 Lambsquarters Persn Speedwell 0 Rape 3 Ryegrass 0 Sugar beet 4 Sunflower o WheAt ~Cnrinn) O
Wheat (Winter) 0 Wild buckwheat 0 Wild mustard 0 Wild oat (1) 0 Wild oat (2) 0 Wlld radish 0 Winter B~rley 0 .. :
- .

:

WOsl/ls47~ PCT/US91~01075 ~.,~;~, r ,~ 9 TEST H
~eeds of alfalfa (Medicaoo ~ativa), bean (Ph~seol,u~ vulQari~), bluegrass (~Q~ ~r~tensis), cabbage (~ass~ca raDa), carrot (~aucus sativa), corn (Z~ m~Y~), fla~ (Linum usitatissimUm)~ lettuce (Lactu~a sativa), lupine (Lupinus albus), oats (Avena sativa), onion (alli~m ~p~), pea (sativum), peanut (Ara~his hYDo~aea), potato (Solanum tuberosum), rye (Secale cereal), sorghum (Sorahum bicol~), sunflower (Helianthus anD~y~), and tomato (LYcopersicon esculent~m) were planted and treated preemergence with a test chemical dissolved in a non-phytoto~ic solvent. These crop species were also treated with postemergence applications of the test chemical.
Plants ranged in height from four to twenty cm (two to three leaf stage) when post-emergence applications were applied. Treated plants and controls were grown under greenhouse conditions for appro~imate'y twenty-four days, after which all plants treated with the test chemical were compared to untreated controls and visually evaluated for injury response.
Application rates for the test chemical are shown in Table H. Plant response ratings, summarized in Table H, are from 0 to 10 where 0 $s no injury and 10 i5 complete control. A dash ~-) response means no t,est result.

2 ~ ; 9 Table H
COMPOUND
Rate (250 g/ha) 5 PREEMERGENCE
Alfalfa 9 Pean 9 Pluegrass 10 Cabbage 10 Carrott 9 Corn 8 Fla~ 10 Lettu~e 9 Lupine 10 Oats 9 Onion 10 Pea 10 Peanut 9 Potato 10 Rye 10 Sorghum 10 Sunflower 10 Tomato 9 ` - . . . ~ :

, . . ..
, wosl/ls478 PCT/US91/01075 ~ .
127 2~`~

Table H
COMPOUND
Rate (125 g/ha) 5 POSTEMERGENCE
Alfalfa 9 Bean 10 Bluegrass 6 Cabbage 9 Carrott 10 Corn 8 Flas g Lettuce 9 Lupine 10 Oats 9 Onion 8 Pea 7 Peanut 9 Potato 7 Rye 9 Sorghum 10 Sunflower 10 Tomato 9 , WO 91/15478 PCr/VS91/01075 Table H
COMPOUND
Rate (125 g/ha) 5 PREEMERGENCE
Alfalfa 9 Bean 9 Bluegrass 9 Cabbage 10 Carrott 9 Corn 3 Fla~ 10 Lettuce 9 Lupine 10 Oats 9 Onion 10 Pea 10 Peanut 9 Potato 9 Rye 10 Sorghum 10 Sunflower 10 Tomato 9 , ....

wosl/ls47~ PCT/US91/01075 .,~.-, ~
~ .~, Table H
COMPOUND
R~te (64 g/ha) 5 POSTEMERGENCE
Alfalfa 8 ~ean 10 ~luegrass 6 Cabbage 9 Carrott 9 Corn 7 Fla~ 6 Lettuce 9 Lupine 10 o~ts 7 Onion 7 Pea 6 Peanut 8 Potsto 7 Rye 9 Sorghum 9 Sunflower 10 Tomato 8 ~`
~' J ~'~ ~ 130 Table H
COMPOUND
Rate (64 g/ha) 5 PREEMERGENCE
Alfalfa 9 ~ean 9 Bluegrass 9 Cabbage 10 Carrott 8 Corn 5 Fla~ 9 Lettuce 10 Lupine 8 Oats 9 Onion 10 Pea 10 Peanut 9 Potatn g Rye 10 Sorghum 10 Sunflower 9 ~omsto 9 ~5~

Table H
COMPOUND
Rate (32 g/ha) 5 POSTEMERGENCE
Alfalfa 8 Bean 9 Pluegrass 7 Cabbage 6 Carrott 9 Corn 3 ~las 6 Lettuce 10 Lupine 10 Oats 7 Onion 7 Pea 5 Peanut 9 Pot~to 7 Rye 9 Sorghum 9 Sunflower 10 Tomato 7 . . : -,"

Wogl/15478 PCT/US91/01075 Table H
COMPOUND
Rate (32 g/ha) 5 PREE~ERGENCE
Alfalfa 7 Bean 9 81uegrass 8 Cabbage 9 Carrott 7 Corn 3 Fla~ 7 Lettuce 7 Lupine 6 Oats 9 Onion 9 Pea 10 Peanut 7 Potato B
Rye 9 Sorghum 10 Sunflower 9 Tomato 9 WO 91 t 15478 PCI / US9 1/01075 T~ble H
COMPOUND
Rate (16 g/ha) 5 POSTEMERGENCE
Alfalf B 6 Bean 9 Bluegrass 6 Csbbage 7 Carrott 9 Corn Fla~ 6 Lettuce 9 Lupine 10 Oats 8 Onion 6 Pea 6 Peanut 7 Potato 4 Rye 7 Sorghum 9 Sunflower 10 Tomato 4 - .

WO91/1~78 PCT/US91/0~075 2.. 1~ ~9 134 ~able H
COMPOUND
Rate (16 g/ha) PREEMERGENCE
Alfalfa 6 Bean 2 Bluegrass 6 Cabbage 9 Carrott 2 Corn Fla~ 6 Lettuce 3 Lupine 8 O~ts g Onion 7 Pea 10 Peanut 6 Potato 6 Rye 9 Sorghum 9 Sunflower 9 ~omato 8 WO 91/15~78 PCI`/US91/0107~ ~

9.~9 Table H
COMPOUND
Rate (B g/ha) 5 POSTEMERGENCE
Alfalfa 3 Bean 8 Bluegrass 6 Cabbage 2 Carrott 8 Corn 0 Fla~ 3 Lettuce 9 Lupine 10 OAts 7 Onion 6 Pea 6 Peanut 6 Potato 2 Rye 7 Sorghum g Sunflower 10 Tomato 3 , .
:~, . . -

Claims

What is claimed is:

1. A compound selected from I

wherein:
A is OR1 or N(CH3)2;
R1 is C1-C3 alkyl, CH2CH-CH2, CH2C?CH, CH2CH2C1 or CH2CH2OCH3;
R2 is CH2F, CHF2, CHFCH3 or CH2CN;
X is CH3 or OCH3; and Y is H, C1, CH3, C2H5, OCH3 or OCF2H;
and their agriculturally suitable salts; provided that when Y is C1, then X is OCH3.

2. A compound of Claim 1 wherein A is OR1; and R1 is CH3, CH2CH3 or CH(CH3)2.

3. A compound of Claim 2 where when one of X and Y is CH3, then the other of X and Y is other than OCH3.

4. The compound of Claim 1, methyl 3-(cyanomethyl)-2-[[[[(4,6-dimethyl-2-pyrimidinyl)amino]carbonyl]-amino]sulfonyl]benzoate.

5. The compound of Claim 1, methyl 2-[[[[(4-chloro-6-methoxy-2-pyrimidinyl)amino]carbonyl]amino]-sulfonyl]-3-(cyanomethyl)benzoate.

6. The compound of Claim 1, methyl 3-(cyanomethyl)-2-[[[[[(4-(difluoromethoxy)-6-methoxy-2-pyrimi-dinyl]amino]carbonyl]amino]sulfonyl]-benzoate.

7. The compound of Claim 1, methyl 3-(difluoromethyl)-2-[[[[(4-methoxy-2-pyrimidinyl)amino]carbonyl]-amino]sulfonyl]benzoate.

8. The compound of Claim 1, methyl 3-(fluoromethyl)-2-[[[[(4-methoxy-2-pyrimidinyl)amino]carbonyl]-amino]sulfonyl]benzoate.

9. The compound of Claim 1, methyl 2-[[[[(4,6-dimethoxy-2-pyrimi-dinyl)amino]carbonyl]amino]sulfonyl]-3-(fluoromethyl)benzoate.

10. The compound of Claim 1, ethyl 2-[[[[(4-chloro-6-methoxy-2-pyrimidinyl)amino]carbonyl]amino]-sulfonyl]-3-(fluoromethyl)benzoate.

11. A compound selected from II

wherein:
A is OR1 or N(CH3)2;
R1 is C1-C3 alkyl, CH2CH-CH2, CH2C?CH, CH2CH2C1 or CH2CH2OCH3;
R2 is CH2F, CHF2, CHFCH3 or CH2CN; and Z1 is C1 or NHSiR3R4R5;
R3 is C1-C4 alkyl;
R4 is C1-C4 alkyl; and R5 is C1-C4 alkyl.

12. A compound of Claim 11 wherein A is OR1 and R1 is C1-C2 alkyl.

13. A compound of Claim 12 wherein R3 and R4 are CH3 and R5 is C(CH3)3.

14. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of Claim 1 and at least one of the following: surfactant, solid diluent or liquid diluent.

15. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of Claim 2 and at least one of the following: surfactant, solid diluent or liquid diluent.

16. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of Claim 3 and at least one of the following: surfactant, solid diluent or liquid diluent.

17. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of Claim 4 and at least one of the following: surfactant, solid diluent or liquid diluent.

18. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of Claim 5 and at least one of the following: surfactant, solid diluent or liquid diluent.

19. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of the com-pound of Claim 1.

20. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of the com-pound of Claim 2.

21. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of the com-pound of Claim 3.

22. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of the com-pound of Claim 4.

23. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of the com-pound of Claim 5.

24. The method of Claim 22 wherein the locus to be protected is corn.

25. A method for controlling the growth of undesired vegetation in wheat or barley which comprises applying to the wheat or barley an effective amount of the compound of Claim 9.