CA1203536A - Herbicidal sulfonamides - Google Patents

Abstract

Abstract of the Disclosure Novel o-aminosulfonylphenyl acetic acid derivatives are useful as plant growth regulants and herbicides.

Description

lZ03~36 Title HERBICIDAL SULFONAMIDES
Background of the Invention This invention relates to o-aminosulfonylphenyl acetic acid derivatives which are useful as plant growth regulants and herbicides.
French Patent No. 1,468,747, published 1967 February 10 discloses the following para-substituted phenylsulfonamides, useful as anti-diabetic agents:

~___~ O ,N--~
R ~ _ SO2_NH_c_NH _ </

where R = H, halogen, CF3 or alkyl.
- 15 Logemann et al., Chem Ab., 53, 1805~ g (1959), disclose a number of sulfonamides, including uracil derivatives and those having the formula:

H3C ~ _ SO2NHCNHR

wherein R is butyl, phenyl or <\ ~ and N ~
Rl Rl is hydrogen or methyl. When tested for hypoglycemic effect in rats (oral doses of 25 mg/100 g), the compounds in which R is butyl or phenyl were most potent. The others were of low potency or inactive.
Wojciechowski, J. Acta. Polon. Pharm. 19, P.
121-5 (1962) lChem. Ab., 59 1633 e] describes the synthesis of N-[(2,6-dimethoxyprimidin-4-yl)-aminocarbonyl]-4-methylbenzenesulfonamide:
~OCH3 ~ jO ~
C 3 ~ SO2NH_c_NH ~ N

:12()3S36 In U.S. Patent 4,127,405, the following compounds are taught to have herbicidal acti~ity:

S W N ~
Rl-so2-NH-c-NH ~ ~ \N
` N.

wherein R3 R4 Rl is ~ R5 , lS R7 R6 8 ~ or Rg Rlo R3 and R6 are independently hydrogen,.fluorine, chlorine, bromine, iodine, alkyl of 1-4 car-bon atoms, alkoxy of 1-4 carbon atoms, nitro, trifluoromethyl, cyano, C~3S(O)n~ or C~3C~2S~o)n~;
R4 is hydrogen, fluorine, chlorine, bromine or - methyl;
R5 is hydrogen, fluorine, chlorine, bromine, methyl or methoxy;
R7 is hydrogen, fluorine, chlorine, bromine, alkyl of 1-2 carbon atoms or alkoxy of 1-2 - carbon atoms;
R8 is hydrogen, methyl, chlorine or bromine;
Rg and Rlo are independently hydrogen, methyl, chlorine or bromine;

W and Q are independently oxygen or sulfur;
n is 0, 1 or 2;
X is hydrogen, chlorine, bromine, methyl, ~ ethyl, alkoxy of 1-3 carbon atoms, tri-fluoromethyl, CH35- or CH3OCH2-; and Z is methyl or methoxy; or their agriculturally suitable salts; provided that:
(a) when R5 is other than hydrogen, it least one of R3, R4, R6 and R7 is other than hydrogen and at least two of R3, R4, R6 and R7 must be hydrogen;
(b) when R5 is hydrogen and all of R3, R4, R6 and R7 are other than hydrogen, ~; then all of R3~ R4~ R6 and R7 must be either chlorine or methyl: and ~c) when R3 and R7 are both hydrogen, at least one of R4, R5 or R6 must be hydrogen.
In particular, the patent discloses ortho-substituted compounds wherein the substitution is Cl-C4 alkyl.
The presence of undesired vegetation causes substantial damage to useful crops, especially agri-cultural products that satisfy man's basic food needs, such as soybeans, corn, wheat and the like. The current population explosion and concomitant world food shortage demand improvements in the efficiency of producing these crops. Preventing or minimizing the loss of a portion of such valuable crops by killing, or inhibiting the growth of undesired vegetation is one way of improv~ng this efficiency.
- A wide variety of materials useful for killing, or inhibiting (controlling) the growth of undesired 3S vegetation is available; such materials are commonly lZO3536 referred to as herbicides. The need exists, however, for effective herbicides that destroy or control weeds while not significantly damaging useful crops.
J. ~eterocyclic Chemistry, 8, 947 (1971) dis-closes:

CK3 ~ C-OC2H5 Chemische serichte~ 103, 1992 (1970) discloses:

l~ ~ CN and~ C02H

3s lZ03536 s Summary of the Invention This invention relates to novel compounds of Formula I and their agriculturally suitable salts, suitable agricultural compositions containing them, and their method of use as general and selective pre-emergence and post-emergence herbicides and as plant growth regulants.

R~ R2 (I) . wherein L is C02Rlo, CONR3R4 or CN;
R is H, F, Cl, Br, NO2, CF3, Cl-C3 alkyl or Cl-C3 alkoxy;
Rl is H or Cl-C4 alkyl;
R2 is H or CH3;
R3 is H, Cl-C4 alkyl or OCH3;
R4 is H or Cl-C4 alkyl;
R3 and R4 can be taken together to form - (CH2) 4- ~ ~ (CH2) 5 - (CH2CH2) 2;
R8 is H, CH3 or OCH3;
Rlo is H, Cl-C4 alkyl, C3-C4 alkenyl, CH2CH2Cl or CH2CH20CH3;
. A is ~O~ , ~ or lZ03536 W is O or S;
X is H, Cl, Br, CH3, CH2CH3, Cl-C3 alkoxy~ CF3 ~ SCH3 or CH2OCH3;
Y is CH3 or OCH3;
Z is N, CH, CCl, CBr, CCN, CCH3, CC82CH3, CCH2CH2Cl or CCH2CH=CH2;
yl is H, CH3, OCH3 or OCH2CH3;
and Q is O or CH2;
and their agriculturally suitable salts;
provided that:
(1) when L is CONR3R4, then Z is CH or N;

(2) when R3 is OCH3, then R4 is CH3; and

(3) when W is S, R8 is H.
Preferred in increasing order for their higher activity and/or more favorable ease of synthesis are:
(1) Compounds of the generic scope wherein L is CO2Rlo, W is O, Z is N, CH, CCl, CBr or CCH3, and R8 is H or CH3;
(2) Compounds of Preferred tl) wherein Z is CH or N, X is CH3 or OCH3, and R
and R2 are H;
- (3) Compounds of Preferred t2) wherein A is X
N ~
~0~ ' N
R8 is H and R is H;

(4) Compounds of Preferred ~3) wherein Rlo is CH3 or CH2CH3.

SpecificallY Preferred for highest activity and/or most favorable ease of synthesis are:
2-tt(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-aminosulfonyl]benzeneacetic acid, methyl ester;
2-[t(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-aminosulfonyl]benzeneacetic acid, methyl ester;
2-t[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-aminosulfonyl]benzeneacetic acid, methyl ester;
2-~[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-aminosulfonyllbenzeneacetic acid, methyl ester;
2-1[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino-carbonyllaminosulfonyllbenzeneacetic acid, ~ethyl ester 2-~[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-aminosulfonyl)benzeneacetic acid, ethyl ester; and 2-tt(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-aminosulfonyllbenzeneacetic acid, ethyl ester.

i 2' s lZ03536 This invention also relates to novel compounds of Formula II which are useful intermediates for the preparation of the herbicidal compounds of Formula I.

R~ R2 R ~ so~NHCo~H ~ O ~
Cl (II) wherein L, R, Rl, and R2 are as previously defined, and Z is CH or N; provided that when R3 is OCH3, then R4 is CH3, and that Rlo cannot be H.
This invention also relates to novel compounds - of Formula III which are useful intermediates for the preparation of the compounds of Formula I.

R~ /R2 ~ C-L

(III) wherein L is CO2Rlo;
R, Rl, R2 and Rlo are as previously defined;
provided that R1o cannot be H.

lZ~3S36 g ~
Detailed Description of the Invention 'SYnthe s i s As shown in E~uation 1, the com~ounds of Formula I can be prepared by combining an appropriately sub-stituted 2-aminoheterocycle of Formula IV with an appropriately substituted sulfonyl isocyanate of For-mula III R, Rl, R2, R8 and A àre as previously defined, and L is C02Rlo, provided that Rlo cannot be H.
10 Equation 1 R~ ~ 2 .. ~ /

R~ + H-N-A ~ R~C-L
S2 N R8 So2-NH-c-N-A
` 15 R8 III IV
The reaction is best carried out in inert aprotic organic solvents e.g. methylene chloride, 20 tetrahydrofuran or acetonitrile, at ambient pressure and temperature. The mode of addition is not critical; however, it is often convenient to add the sulfonyl isocyanate to a stirred suspension of the aminoheterocycle. Since the isocyanates often are 25 liquids, their addition is more easily controlled.
The reaction is generally exothermic. In some cases, the desired product is insoluble in the warm reaction medium and crystallizes from it in pure form. Products soluble in the reaction medium are isolated by evaporation of the solvent, trituration of the solid residue with solvents such as l-chlorobu-tane, ethyl ether or pentane and filtration.

12~3536 . '' The intermediate sulfonyl isocyanates of Formula III in which L is CO2Rlo, provided that Rlo can-not be H, are also novel compounds and can be prepared by reacting the corresponding sulfonamides (V) with phosgene in the presence of an alkyl isocyanate e.g.
butyl or cyclohexyl isocyanate at reflux in a sol-vent such as chlorobenzene, according to the procedure of H. Ulrich and A. A~ Y. Sayigh, Newer Methods of Preparative Orqanic ChemistrY, Vol. VI, p. 223-241, Academic Press, New York and London, W. Foerst, Ed.
In cases where formation of the desired sulfonyl iso-cyanate is difficult by the above procedure, the pre-formed sulfonylurea from the reaction of butyl isocya-nate with the appropriate sulfonamide is treated with phosgene according to the above reference.
Alternatively, the process of Ulrich and Sayigh can be varied by the addition of a tertiary base to the reaction mixture as shown by Equation 2 in which L is CO2Rlo~ provided that R10 cannot be lZ~3~36 Equation 2 R~ / 2 R~ / 2 ~ C-L DABCO ~ ~C-L
R--~ T + COC12 n C4HgNCO ) R--.
S SO 2NH2 xylene ~ SO 2NCO

V III
A mixture of the appropriate benzenesulfonamide ~V), an alkyl isocyanate such as butyl isocyanate and a ca~alytic amount of 1,4-diazal2,2,2]bicyclooctane (DABCO) in xylene or other inert solvent of suffi-ciently high boiling point (e.g. ~135) is heated to approximately 135. Phosgene is added to the mixture until an excess is present as indicated by a drop in the boiling point. The mixture is heated further to drive off the excess phosgene. After the mixture is cooled and filtered to remove a small amount of in-soluble by-products, the solvent and alkyl isocyanate are distilled off in vacuo leaving a residue which is the crude sulfonyl isocyanate ~III). ~
The preparation of sulfonamides from ammonium hydroxide and sulfonyl chlorides is widely reported in the literature, e.g., Crossely et al., J. Am Chem.
Soc. 60, 2223 (1938).
Certain sulfonyl chlorides are best prepared by chlorosulfonation of a substituted ~enzene according to the teaching of ~. T. Clarke et al. Org. Synth.
Coll. Vol. 1, 2nd Ed. 1941, p. 85. Other benzene-sulfonyl chlorides are best made by diazotization of the appropriate aniline with sodium nitrite in HCl, followed ~y reaction of the diazonium salt with sulfur dioxide and cuprous chloride in acetic acid according to the teaching of ~. L. Yale and F. Sowinski, J- Or~. Chem., 25, 1824 (1960).

The synthesis of heterocyclic amine derivatives has been reviewed in "The Chemistry of Heteracylic Compounds", a series published by Interscience Publ., New Yor~ and London. 2-Aminopyrimidines are described

5 by D. J. Brown in "The Pyrimidines", Vol. XVI of the above series.
2-Amino-1,3,5-triazines can be synthesized according to the methods described by~E. M. Smolin and L. Rapaport in "s-Triazines and Derivati~es", 10 Vol. XIII of the same series.
The preparation of fused ring pyrLmidine amines are disclosed in various publications, such as:
Braken et al., J. Am. Chem. Soc., 69, 3072 ~1947);
Mitten and ~harlacharya, Quart. J. Ind. Chem. Soc. 4, 15 152 (1927), Schrage and Hitchings, J. Org. Chem., 16, 1153 (1951); Svab et al., Coll. Czech Commun. 32, 1582 (1967).
Compounds of Formula IX are prepared by the reaction of about two equivalents of aqueous sodium hydroxide with the compounds of Formula I in which Rlo is Cl-C4, preferably methyl (VIII), followed by acidification of the solution. This process is , illustrated in Equation 3, wherein R, Rl, R2, R8 and A are as previously defined.
Equation 3 R ~ O ~ R ~ C-CO2H

VIII IX

~ZV3536 The reaction is carried out over the course of 2-6 hours in water, by stirring the compound of For-mula v~II with two equivalents of sodium hydroxide or potassium hydroxide at ambient temperature. The aqueous solution is then acidified with hydrochloric or sulfuric acid, which causes the compound of Formula IX to precipitate out. It is then isolated by filtra-tion.
Compounds of Formula X are prepared by reacting an appropriately substituted compound of Formula I in which Rlo is Cl-C4 alkyl, preferably methyl (VIII), with a dialkylaluminum-N-alkylamide deriva-tive, as shown in Equation 4, wherein R, Rl, R2, - R3, R4, R8 and A are as previously defined.
E~uation 4 R~ /R2 ~,C-C02CH3 R ~ I O + (cH3)2Al-NR3R4 ~--S02-NH-C-N-A
. R8 VIII

R~ /R2 O
CH2C12 ) R ~

X

35.

12(~3536 The intermediate alkylaminoaluminum compounds are prepared according to A. 3asha, M. Lipton and S. W. Weinreb, Tetrahedron ~etters, 4171 ~1977) by reacting the trialkylaluminum, preferably trimethyl-aluminum, and the corresponding amine. The (CH3)2Al-NR3R4 intermediate is co-mingled with a suspension of the compound of Formula VIII in an inert solvent, preferably methylene chloride, and the mixture is refluxed for one to twenty-four hours. The product is isolated by adding aqueous hydrochloric acid to decompose the resulting complex, and then evaporating the methylene chloride phase. The desired product can be further purified by recrystallization or column chromatography.
Compounds of Formula XIII can be~prepared by reacting an appropriately substituted sulfonamide of Formula XI with the methylcarbamate of the appropriate aminoheterocycle (XII) in the presence of an equiva-lent amount of trimethylaluminum, as shown in Equation 5, wherein R, Rl, R2, R8 and A are as previously defined.
Equation S
Rl R2 ~ C-CN o 25 R ~ CH30-C-N-A

XI XII

R~ / 2 Al~C 3)3R ~ 502-NH-C-N-A

XIII

lZ(33536 The reaction of Equation 5 is best carried out in an-inert solvent e.g. methylene chloride at 10-45 and atmospheric pressure. The preferred mode of addition is to add the trimethylaluminum to a solu-s tion or slurry of the sulfonamide ~XI); a mildly exo-thermic reaction occurs accompanied by the evolution of gas. The addition of the heterocyclic carbamate (XII) is then made and the mixture is stirred at ambient to reflux temperature for 6 to 48 hours. ~he addition of aqueous acid such as dilute hydrochloric or acetic acid removes organic salts from the product contained in the organic phase. Evaporation of the methylene chloride yields the crude product, which can be purified by recrystallization or column chromato-` 15 graphy.
, Some of the compounds of Formula I can also be prepared by the method shown in Equation 6, using the novel intermediates of Formula II, wherein L, R, Rl, R2, R3, R4 and Rlo are as previously defined, and wherein Z is CH or N, and R12 is Cl-C3 alkyl.

3s ~Z~3~36 Equa t ion 6 (6a) R2 ~2 Rl-C-L Cl Rl-C-L N
1~;o2 2 N--< ~S02NHC-NH

R Cl ~J Cl Z Cl V XV II

( 6b) ,R2 OR12 R -C-L O N--<
SO2NHC-NH--~O Z

Cl R
XVI

~6c) ,R2 OR12 Rl-C-L O N--( ` XVI ~ ~ S02NHC-NH--~Oz XVI I

~2g~3S36 Reaction steP (6a) In Reaction Step ~6a), an aromatic sulfonamide of Formula V is contacted with a heterocyclic iso-cyanate of Formula Xv to yield an N- (haloheterocyclic-aminocarbonyl)aromatic sulfonamide of Formula II.
The heterocyclic isocyanates used in Reaction (6a) may be prepared according to methods described in Swiss Patent 579,062, U.S. Patent 3,919,228, U.S.
Patent 3,732,223 and Anqew Chem. Int. Ed. 10, 402 (1976), The aromatic sulfonamide and the heterocyclic isocyanate are contacted in the presence of an inert organic solvent, for example, acetonitrile, tetrahy-` 15 drofuran (THF), toluene, acetone or butanone.
Optionally, a catalytic amount of a base, e.g.
1,4-diazabicyclol2.2.21octane (DABCO), potassium carbonate, sodium hydride or potassium tert-butoxide, may be added to the reaction mixture. The quantity of base constituting a catalytic amount would be obvious to one skilled in the art. ~he reaction mixture is preferably maintained at a temperature of about 25 to 110, and the product can generally be recovered by cooling and filtering the reaction mixture. For reasons of efficiency and economy, the preferred solvents are acetonitrile and THF, and the preferred temperatur~e range is about 60 to 85C.
Reaction stePs (6b) and (6c) In Reaction Steps (6b) and (6c), one or two of the halogen atoms on the heterocyclic ring of the compound of Formula II is displaced by a nucleophilic species. Generally this may be done by contacting the compound of Formula II either with alkanol, R12OH or with alkoxide, -OR12, where R12 is as defined above.

12~33536 Thus, in Reaction Step (6b), a compound of For-mula II can be contacted with at least one equivalent of alkanol, R12OH. This reaction is sluggish, how-ever, and it is preferred to contact the compound of ~ormula II with at least two equivalents of alkoxide, OR12. The alkoxide can be provided in a number of ways:
(a) The compound of Formula II can be suspended or dissolved in an alkanol solvent, R12OH, in the presence of at least two equivalents of alkoxide, OR12. The alkoxide can be added directly as alkali metal or alkaline earth metal alkoxide or can be gen-erated by the addition to the alkanol solvent of at least two equivalents of a base capable of generating alkoxide from the solvent. Suitable bases include, but are not limited to, the alkali and alkaline earth metals, their hydrides and tert-butoxides.
For example, when R12 is methyl, the compound of Formula II could be suspended or dissolved in methanol in the presence of two equivalents of sodium methoxide. Alternatively, two equivalents of sodium hydride could be used in place of the sodium methoxide.

12035~

~b) $he c ~pound of Formula II can be suspended or dissolved in an inert solvent in the presence of ~t least two equivalents of alkoxide, OR12.
Suitable inert solvents include, but are not limited to, acetonitrile, THF
and dimethylformamide. The alkoxide may be added directly as alkali metal or alkaline earth metal alkoxide or may be generated from alkanol and a base as described in (a) above. Por example, when R12 is methyl, the compound of Formula II could be suspended or dissolved in $HF in the presence of two equivalents of sodium methoxide. Alternatively, two equiva-lents each of methanol and sodium hydride could be used instead of sodium methoxide.
. .
For reasons of economy and efficiency, procedure (a) is the more preferred method.
It should be noted that two equivalents of alkoxide are required for Reaction Step (6b) whereas only one equivalent of alkanol is needed for the same 2S process. This difference is due to the reaction which is believed to oc¢ur between the alkoxide and the sulfonyl nitrogen of the sulfonamide of Formula II.
When alkoxide is used, the first equivalent of alkoxide removes a proton from the sulfonyl nitrogen, and it is only the second equivalent which effects displacement of the halogen. As a result, two equivalents of alkoxide are required. $he resulting salt must be acidified, e.g., with sulfuric, hydrochloric or acetic acid, to yield a compound of 3S Formula XVI. Applicant, of course, does not intend to be bound by the mechanism described above.

~ 1203536 In Reaction Step (6c), a compound of Formula XVI
is contacted with either one e~uivalent of methanol, or with two equivalents of methoxide, -OCH3. When methoxide is used, it may be provided in either of the 5 methods described above in connection with Reaction Step (6b), and the resulting salt can be acidified to yield a compound of Formula XVII.
When R12 = CH3, Reaction Steps (6b) and (6c) may be combined. Thus, a compound of Formula II may be contacted either with at least two equivalents of methanol or with at least three equivalents of methoxide.
For a compound of Formula II, certain reaction conditions will favor displacement of only one of the chlorines. These conditions are the use of low tem-peratures and, when alkoxide is used, the slow addi-tion of the stoichiometric amount of alkoxide or alkoxide-generating base to the medium containing the compound of Formula II.
When alkoxide is used, both Reaction Steps (6b) - and (6c) are preferably run at temperatures within therange of about -10 to 80C, the range of about 0 to 25C being more preferred. Reaction Steps (6b) and (6c) are more sluggish when alkanol is used instead of alkoxide, and more drastic conditions are required for the reaction to go to completion. Thus, higher tem-peratures, up to and including the boiling point of the-alkanol itself, are required.
As shown in Equation 7, compounds of Formula XIX, in which R, Rl, R2, L and A are as previously defined, are prepared by the reaction of an appropri-ately substituted sulfonamide, (V), with a heterocy-clic isothiocyanate of Formula XVIII.

i203536 Equation 7 . ~

C !L R~C/L2 R~ + SCN-A ~ R ~ S
5~--S2NH2 ~S02-NH-C-NH-A

V XVIII XIX
The Reaction of Equation 7 is best carried out by 10 dissolving or suspending the sulfonamide and isothiocyanate in a polar solvent e.g. acetone, acetonitrile, ethyl acetate or methyl ethyl ketone, adding an equivalent of a base e.g. potassium carbonate and stirring the mixture at ambient 15 temperature up to the reflux temperature for one to twenty-four hours. In some cases, the product precipitates from the reaction mixture and can be removed ~y filtration. The product is stirred in dilute mineral acid, filtered and washed with cold 20 water. Tf the product does not precipitate from the reaction mixture it can be isolated by evaporation of the solvent, trituration of the resiaue wth dilute mineral acid and filtering off the insolub~e product.
The heterocyclic isothiocyanates which are used 25 in the procedure of Equation 7 are prepared, for - example, accordin~ to the method of Japan Patent Application Pub: Rokai 51-143686, June 5, 1976, or that of W. Abraham and G. Barnikow, Tetrahedron 29, 691-7 (1973).
.

~ZC~3536 Agriculturally suitable salts of compounds of Formula I are also useful herbicides and can be prepared in a number of ways known to the art. For example, metal salts can be made by treating compounds of Formula I with a solution of an alkali or alkaline earth metal salt having a sufficiently basic anion (e.g., hydroxide, alkoxide, carbonate or hydride).
- Quaternary amine salts can be made by similar techniques.
Salts of compounds of Formula I can also be prepared by exchange of one cation for another.
Cationic exchange can be effected by direct treatment of an aqueous solution of a salt of a compound of Formula I (e.g., alkali metal or quàternary amine salt) with a solution containing the cation to be exchanged.
This method is most effective when the desired salt containing the exchanged cation is insoluble in water, e.g., a copper salt, and can be separated by filtration.
Exchange may also be effe~ted by passing an aqueous solution of a salt of a compound of Formula I
~e.g., an alkali metal or quaternary amine salt) through a column packed with a cation exchange resin containing the cation to be exchanged. In this method, the cation of the resin is exchanged for that of the original salt and the desired product is eluted from the column. This method is particularly useful when the desired salt is water soluble, e.g., a potassium, sodium or calcium salt.
Acid addition salts, useful in this invention, can be obtained by reacting a compound of Formula I
with a suitable acid, e.g., ~-toluenesulfonic acid, trichloroacetic acid or the like.

r 1203536 In the following examples, all parts are by weight and temperatures in C unless otherwise indicated.
Example 1 5 Methyl o-Isocyanatosulfonylbenzeneacetate A mixture of 22.9 g methyl o-aminosulfonylben-zeneacetate, 13.5 g n-butyl isocyanate, 15.2 g potas-sium carbonate and 250 ml methyl ethyl ketone was stirred and refluxed for three hours. The reaction mixture was cooled, poured into 1250 g of ice-water, and acidified to pH 1.5 with concentrated HCl. The product was filtered, washed and dried. The crude product was recrystallized from l-chlorobutane to yield 24.3 g of purified N-(n-butyl)sulfonylurea lS derivative of methyl o-isocyanatosulfonylbenzene-acetate, m.p. 164-166 (dec.).
To 16.4 g of the above N-(n-butyl)sulfonylurea derivative was added 150 ml of xylene and 0.2 g DABCO. The mixture was stirred and heated until 30 ml of xylene had been distilled off. The distillation head was replaced with a dry-ice reflux condenser, and then phosgene was slowly passed into the reaction mix-ture, which was maintained at 130-138, over about one hour. When no more phosgene was taken up, the mixture was heated at 132-133 under slow phosgene reflux for one hour longer. The reaction mixture was cooled to room temperature, filtered to remove some solids and concentrated in vacuo to yield 25.0 g of the desired sulfonyl isocyanate product as an oil.
Example 2 Methyl 2-t[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-aminosulfonYl]benzeneacetate The 25 g of methyl o-isocyanatosulfonylbenzene-acetate from Example 1 was dissolved in 150 ml dry a~-etonitrile, and 0.2 g DABCO was added. To the stirred solution at 27 was added all at once 7.6 g of 2-amino-4,6-dimethoxypyrimidine. The temperature rose rapidly to 42. The reaction mixture was then stirred and heated at 48-50 for two hours, and stirred at 5 ambient temperature for a further sixteen hours. The product was recovered by filtration and dried; 16.3 g of the desired sulfonylurea was obtained, m.p.
193-196 (dec.). The product absorbed in the IR at 1730, 1610 and 1570 cm 1. It showed N~ absorption at ~3.8 (s, 3H), methyl ester: ~4.1 (s, 6H), pyrimi-dine methoxyl groups; ~4.3 (s, 2~), benzeneacetic group; ~6.2 (s, lH), pyrimidine ring hydrogen;
~7.3-8.5 ~m, 4H), aromatic hydrogens.
Anal. Calcd. for C16H18N407S: C, 46.82;
~1, 4.42; N, 13.66; S, 7.81.
Found: C, 46.9, 47.0;
H, 4.4, 4.4, N, 14.0, 14.0; S, 8.3, 8Ø
All data are consistent with the structure of the desired sulfonylurea.
~~ ~ ~~~~ ~~ Example 3 --- - ---2-1[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]amino-sulfonyl]benzeneacetic acid 1.03 9 of the product of Example 2 was added to a stirred solution of 0.5 g of commercial 50% aqueous sodium hydroxide mixed with 25 ml of water at am~ient temperature. A clear solution was obtained after a few minutes. Stirring at ambient temperature was main-tained for two hours. 2N hydrochloric acid was added dropwise to pH 2, causing the desired product to pre-cipitate out. The solid product was filtered, washedand dried; 0.95 g was obtained, m.p. 173-175 ~dec.).
The product absorbed in the IR at 1730, 1690, 1610 and 1580 cm 1. It showed NMR absorption at ~4.0 (s, 6H), pyrimidine methoxyl groups; ~4.1 (s, 2H), ben-zeneacetic group; ~ 5.9 (s, lH), pyrimidine ring hydro-gen; ~7.3-8.4 (m, 4H), aromatic hydrogens; ~10.5 (s, lH), carboxylic acid. The spectral data are consis-tent with the structure of the desired sulfonylurea.
Example 4 S Methyl 2-11(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-aminocarbonyl]aminosulfonYllbenzeneacetate 2.3 g Methyl o-isocyanatosulfonylbenzeneacetate prepared as described in Example 1, and 0.03 9 DABCO
were dissolved in 30 ml dry acetonitrile. 1.2 g of 2-Amino-4-methoxy-6-methyl-1,3,5-triazine was added all at once to the stirred solution, which was heated for two hours at 50-55, then for sixteen hours at ambient temperature. The reaction mixture was fil-tered and the solids obtained were washed and dried (1.0 9). The solids, which were a mixture of the desired product and unreacted 2-amino-4-methoxy-6-methyl-1,3,5-triazine, were dissolved in 100 ml methylene chloride and washed with 0.3 N hydrochloric acid, which removed unreacted aminotriazine. Evapora-tion of the methylene chloride yielded 0.7 g of thedesired sulfonylurea; m.p. 162-165 (dec.). The pro-duct showed NMR absorption at ~2.9 (s, 3H), triazine methyl; ~3.9 (s, 3H), methyl ester; ~4.35 (s, 2H), benzeneacetic group; ~4.4 (s, 3H), triazine methoxyl;
~7.4-8.6 (m, 4H) aromatic hydrogens; consistent with the structure of the desired sulfonylurea.
ExamPle S
Ethyl 2-tt(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl~-aminosulfonvl]benzeneacetate Following the procedure of Example 1, ethyl o-aminosulfonylbenzeneacetate was reacted with n-butyl isocyanate to form the N-(n-butyl)sulfonylurea deriva-tive; m.p. 140-142.
Following the procedure of Example 1, the N-(n-butyl)sulfonylurea derivative was reacted with phos-lZ03S3626 gene to form ethyl o-isocyanatosulfonylbenzeneacetate, an oil. 1.35 g of Ethyl o-isocyanatosulfonylbenzene-acetate and 0.015 g of DABCO were dissolved in 15 ml acetonitrile. 0.8 g of 2-Amino-4,6-dimethoxypyrimi-dine was added all at once, and the reaction mixturewas stirred for sixteen hours at ambient temperature.
The product was recovered by filtration; 1.2 g of the desired sulfonylurea was obtained, m.p. 168-172 (dec.). The product showed NMR absorption at ~1.1-1.4 (t, 3H), methyl group of ethyl ester; ~4.2 (s, 6H), methoxyl groups of pyrimidine; ~4.1-4.4 (q, 2H), methylene of ethyl ester; ~4.3 (s, 2H), methylene of benzene acetic group; ~6.3 (s, lH), pyrimidine hydro-gen; ~7.4-8.4 (m, 4H), aromatic hydrogens; consistent with the structure of the desired sulfonylurea.
Example 6 Methyl 2-[[(4,6-dichloropyrimidin-2-yl)aminocarbonyl]-aminosulfonYllbenzeneacetate To 2.3 g of 2-(aminosulfonyl)benzeneacetic acid methyl ester in 30 ml of acetonitrile was added 1.5 g of anhydrous potassium carbonate and 1.6 g of 4,6-di-chloropyrimidin-2-yl isocyanate. The mixture was stirred at room temperature for 6 hours, diluted with 250 g of water and acidified to a pH of about 4. ~he ~ 25 resultin~ solid was filtered and dried to yield 1.6 g of methyl 2-t[(4,6-dichloropyrimidin-2-yl)aminocarbon-yllaminosulfonyl]benzeneacetate, a pale yellow solid, m.p. 115-118C. It showed infrared absorption peaks at 1730, 1600 and 1560 cm 1 and nuclear magnetic resonance peaks at 3.7 ppm, methyl ester group; 4.2 ppm, benzeneacetic group; 6.9 ppm, pyrimidin H;
7.4-7.6 ppm, aromatic hydrogens; consistent for the product.

lZ03536 ExamPle 7 Methyl 2-~(4,6-dimethoxy-1,3,5-tri~zin-2-yl)amino-thioxomethyl]aminosulfonyl]benzeneacetate To 1.1 g of 2-(aminosulfonyl)benzeneacetic acid S methyl ester in 25 ml of ethyI methyl ketone was added 1.9 g of anhydrous potassium carbonate and 1.0 g of 2,4-dimethoxy-1,3,5-triazinyl-6-isothiocyanate. The mixture was stirred at room temperature for 24 hours and then diluted with 200 g of ice-water. The solu-tion was acidified with dilute HCl to a pH of about4. The resulting product was filtered and dried to give`l.2 g of white solid, m.p. 164-168C. It showed infrared absorption peaks at 1750, 1630 and 1570 cm 1 and nuclear magnetic resonance peaks at 3.9, 4.4, 4.5 and 7.6 ppm, consistent for the product.
Example 8 2-1~(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]amino-sulfonyll-N,N-tetramethylenebenzeneacetamide To 1.42 g of pyrrolidine in 100 ml of dry me-thylene chloride at room temperature was added 10 ml of commercial two molar trimethylaluminum in toluene.
The temperature rose by 5. After the resulting solu-tion had been stirred for ten minutes, 4.1 g of the product of Example 2 was added portionwise over five minutes. The reaction mixture was stirred and re-fluxed for sixteen hours. 200 ml of water and 10 ml of concentrated hydrochloric acid was then added to the reaction mixture, the methylene chloride layer was separated, dried by addition of magnesium sulfate, and the solvent removed by distillation at reduced pres-sure. The residue was a gum. Trituration of the gum with 1-chlorobutane resulted in the formation of cry-stals. The product was filtered, washed and dried, 3.8 g was obtained; m.p. 133-135 (dec.). The product absorbed in the IR at 1720, 1650, 1600 and 1550 ` 28 cm 1 It showed NMR absorption ~t ~2.1-2.5 (m, 4H), pyrrolidine hydrogens at positions 3 and 4; ~3.7-4.1 (m, 4H), pyrrolidine hydrogens at positions 2 and 5;
~4.1 (s, 6H), pyrimidine methoxyl groups, ~4.6 (s, 2H), benzeneacetic group; ~6.2 (s, lH), pyrimidine ring hydrogen; ~7.4-8.4 (m, 4H) aromatic hydrogens.
The spectral data are consistent with the structure of the desired sulfonylurea.
Using the general procedures described above, and those of Examples 1 to 8, the following compounds can be made by one skilled in the art.

:

Table I

R~ N ~
Y
~ R R Phys Prop.

C2CH3 H H H CH3 ~H3 C~2CH3 H H H CH3 CH30 CH H 0 194-196(dec) 0~2CH3 H H H CH3 CH3 CH H 0 195-198(dec) 00zCH3 H H H CH30 CH30 N H 0 182-184(dec) C~2C2H5 H H H CH3 CH30 CH H 0 168-170(dec) oO2CH(CH3)2 H H H CH2CH3 CCH3 N H 0 C~2-n-C4H9 H H H CH2CCH3 OC 3 oO2-CH2-CH=CH2 H H H CH30 CH30 CH H 0 174-177(dec) 25C02CH(CH3)2 3 CH30 CH H 0 135-150 C02CH(CH3)2 H H H CH30 CH30 CH H 0 165-168(dec) C~2H H H H CH3 CH3 CH H 0 162-164(dec) C02~ H H H CH30 CH3 CH H 0 207-209(dec) oOzH H ~ .H CH30 CH30 CH H 0 173-175(dec) C~2H H H H CH3 CH3 N
002H H H H CH30 CH3 N H 0 142-144(dec) C02H H H H CH30 CH30 N H 0 155-157(dec) C~2CH3 H CH H CH CH3 CH H 0 C~zCH3 H CH3 3 CH30 CH H 0 C02CH3 . H CH3 H CH30 CH30 CH H 0 Table I ~continued) R 1 2 X y z R8 W

a)2CH3 ~i CH3 H CH30 CH30 N H 0 C12C~3 H n-C4Hg H CH30 CH30 CH H 0 02CH3 3 3 3 C 30 CH H o 2 . 4-Cl H H CH30 CH3 N H 0 C~2CH3 5-Br H H CH30 CH30 CH H 0 15~2C 3 S OCH3 H H CH30 CH30 CH H 0 02CH3 4-n-C3H7 H H CH30 CH3 N H 0 C~)2CH3 3 2C 2 H H CH30 CH30 CH H 0 C~2CH3 3-Cl H H CH30 CH3 N H 0 02CH3 5-Cl H H CH30 CH30 CH H 0 202 3 6-Cl B H CH30 CH3 N H o C~2CH3 H H HCH30 CH3 N CH3 0 ~02CH3 B H HCH3 CH3 N CR3 0 25C~2CH3 H H HCH30 CH30 N CH3 0 C02CH3 B ~ HCH30 CH3 CH CH3 0 02c~3 H H H CH30 CH3 N CH30 0 ~2CH3 H ~ H CH30 CH30 CH CR30 0 ao2~2~2~~3~2 H H HCH30 CH30 C~ H O
3 0 , 3 02 CH2-C~2 H H HCH30 CX3 N H 0 ~2~{2C~12Cl B H 3 3 H 0 a~2~2~2 H3 ~ H HCH30 CH3 N H 0 2~3 E~ H 3 C~3 C~ H S
35)2CEl3 ~ ~ ~CH3 C~30 C~ ~ S
2OE~ HCH30 CH30 CH H S
)2CH3 H H 3 CE~ S

Table I (continued) L ` R 1 2 X Y Z _ W (m.P.) CD2CH3 4-Cl H H CH3 CH3 CH H S
o2CH3 S-Cl H H CH30 CH30 N H S

C~2CH2CH3 HH H CH30 CH30 N H S
o2 CH2-CH CH2 H H H CH3 CH3 CH H S
CD2-CH2-CH=CH2 HH H CH30 CH30 N H S
n C-N(CH3)2 HH H OCH3 3 - CN(C2H5)2 HH H CC2H5 CH3 N H O

n C-N H H H O-n-C3H7 CH3 N H O

n CiN~ H H H O _ C3H7 CH3 N H O

O H
C-N~ HH H OCH3 CH3 N H O
C2H~
O H
C-N~ H H H H CH3 N H O

o 30 C-NH2 H H H O~H3 CCH3 CH H O

n C-N(cH2c~2cH2cH3)2 H H O~H3 O~H3 CH H O
n ,CH3 .. .
C-N~OCH3 H H H C~3 CH3 H O

Table I (continued) Phys. Prop.
L . R ~ ~ X Y Z ~ W ~m.P.) c ~ / 2 J C-N H H H OCH3OCH3 CH H 0 133-135(dec) CH -CH

CH2{~2 O CH-CEI
n / 2 2~

n ~ ~

o H
.. .
C-NCH2CH(CH3)2 H H H CH3 CH3 CH H O
n CN(CH3)2 H H H H CH3 CH H O
O
CN~C2HS)2 H H H H CH3 CH H O

n~C3H7 O C_H
25n ~ 5 C-N-n-C4H~ H H H H CH3 CH H O
.. .
CN(CH3)2 H H H CH3 OCH3 N H O
o CN(C2H5)2 H H H CH3 OCH3 N H O
n CH3 .
C-N~C2H~ H H H CH3 OCH3 CH H O

' H H H CH3 OCH3 CH H O

33 ~
Table I (continued) L R Rl R2 X Y z R8 W (m-P-) O CH
n 1 3 C-N-n-C4Hg H H H CH3 OCH3 CH H O
n C~3 H H H Cl OCH3 N H O

~33 H H H Br OCH3 CCl H O

aX113 H H H Cl CH3 CBr H O

a~CH3 H H H Br CH3 CH H O

O . H H H CH3 CCN H O

C.~H3 H H H H CH3 CCH3 H O

O H H H H CH3 CCH2CH2Cl H O

C{CH3 H H H H CH3 CCH2CH~EI2 H O
O
CN (CH3) 2 4-F H H CH3 CCH3 CH H O

CN(CH3)2 5~ H H CH3 OCH3- CH H O
O
CN (CH3 ) 2 4-Br H H CH3 OCH3 CH H O

CN ~CE~3 ) 2 4-No2 H H CH3 OCH3 CH H O

CN (CH3 ) 2 5-OE3 H H CH3 CCH3 N H O~

CN (CH3 ) 2 5-OCH3 H }I CH3 ~EI3 N H O

CN (C~I3 ) 2 5~CH2CE~2CH3 H H CH3 OCH3 N H O

Table I (continued) R R R Phys. Prop.
L R ~ 2 X Y Z 8 W(m.P.) CN 4-Cl H H CH3 OCH3 CH H O

CN 4-Br H H CH OCH CH H O

10 CN 3-Cl H H OC2 5 C 3 H H O
CN 5-Cl O n 3 7 3 H O
CN 6-Cl H H CF3 CH CH H O

CN H n-c4H9 H CH30 CH30 N H O
CN H n-c3H7 H CH30 CH30 N H O

CN H H H H CH3 CCl H O
20 CN H H H H , CH3 C~3r H O

CN H H H CH3 CH3 CCHzCH2Cl H O
25 CN H H H H CH3 CCHZCH=CH2 H O

,CN H H H CH30 CH30 CH H O

CN H H H CH3 CH3 N CH3 o 3 5 CN H H H CH30 CH30 CH CH3 o '~ 35 Table I (continued) Phys. Prop.
L- R 1 ~ X Y Z 8 W(m.P.) oN . H H H CH30 CH3 N CH30 0 C-N~CH3)2 H H H CH30 CH3 C

C-N(CH3)-2 H H C 3 C 3 CH H 0 C-N(cH3)2 H H H CH3 CH3 N H 0 n C-N(CH3)2 H CH30 CH30 CH H 0 C-N(CH3)2 H H H CH30 CH30 N H 0 _ H CH3 CH3 CH CH3 0 C-N(CH3)2 H H H CH3 CH3 N CH3 0 C-N(cH3)2 H H H CH30 CH3 CH CH3 0 - C-N(cH3)2 H H H CH30 CH3 N CH3 0 ( 3)2 H H H CH30 CH30. CH CH 0 30 C-N(CH3)2 H H H CH3 3 ~

(CH3)2 H H H CH30 CH30 CH CH30 0 C-N(CH3)2 H H 3 CH3 N CH30 0 ~203536 Table I (continued) R Phys. Prop.
L R Rl R2 X Y Z 8 W(m.P.) o C-N (CH3) 2 H H H CEI3 3 S
n C-N (CH3) 2 H H H CH30 CH30 N H S

~2~3536 Table II

R~ /R2 R ~ 502NHCN ~ ~

10 L R Bl R2 Y' Q R8 W

n - CN(CH3)2 H H H H 0 H 0 C02-i_C3H7 H H H CH3 CH2 H
C02-n-C4Hg H H H CH30 ~ CH2 H 0 2-0 C02CH3 H ~ H H CH30 CH2 CH30 0 C2CH3 H H 3 CH~0 0 C2C 3 H H H C~H3 C 2 Table II I
C-L Y' R ~S02NH-C- N~O~

L R Rl R2 8 Y' W
10 C02CH3 ~ H H H H H O

C02CH3 H H H H C 3o CON ~CH3) 2 H H H H CH3 0 ~203S36 Table IV

S R ~ SO ~HCNH ~ ~

Cl 10 L R Rl R2 Z

C02C2H5 . H CH3 H N
15 n C-N(CH3)2 H H H CH

2 0 n ~ 3 C-N\ H (CH3)2CH H CX
l-C3H7 CN ' H H H N
C02-n-C3H7 H CH3-CH-CH2 H CH

C02-n-C4Hg H C(CH3)3 H N
C2CH3 H HC(CH3)CH2CH3 H CH

C2CH3 4-Cl H H CH
30 C2CH3 4-Br H H N

2C 3 5-Cx3 H H CH

C2CH3 5 (CH3)2CX H H N

Table IV (continued) L R Rl R2 Z

2C~33-CH30 H H CH

2CH34-CH3CH2CH2o H H CH
C02CH2CH~cH3)2 4-(CH3)2CH H H N
C0 l-C H H H H CH
10 C02-i-C3H7 H H H N
C02-sec-C4Hg H H H CH

`C02-CH2-CH=CH2 H H H N
15 C02-CH2-CH=CH2 H H H CH

1;i~03~36 Table V

R~ / 2 R ~ C-C02Rlo 10 R Rl R2 Rlo H H ~ 3)2 lS H H H CH3CH2 2 2 H H H CH2=CH-CH2 4-Cl H H CH3 4-CF3 H H ~-~~ ~~

5-Br H H CH3CH2 H H H CH3-CH=CH-CX2 H H ClCH2CH2 ~203536 Formulations Useful formulations of the compounds of Formula I can be prepared in conventional ways. They include dusts, granules, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates and the like. Many of these may be applied directly.
Sprayable formulations can be extended in suitable media and used at spray volumes of from a few liters to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation. The formulations, broadly, con-tain about 0.1~ to 99% by weight of active ingre-dient(s) and at least one of (a) about 0.1% to 20%
surfactant(s) and (b) about 1% to 99.9% solid or li-quid diluent(s). More specifically, they will containthese ingredients in the following approximate propor-tions:
Table VI

Weight Percent*
Active Inqredient Diluent~) Surfactant(s) Wettable Powders 20-90 0-74 1-10 Oil Suspensions, 3-50 40-95 0-15 Emulsions, Solutions, 25 (including Emulsifiable Concentrates) Aqueous Suspension10-50 40-84 1-20 Dusts 1-25 70-99 0-5 Granules and Pellets0.1-95 5-99.9 0-15 High Strength 90-99 0-10 0-2 Compositions * Active ingredient plus at least one of a Surfactant or a Diluent equals 100 weight percent.

lZ03536 Lower or higher levels of active ingredient can, of course, be present depending on the intended use and the physical properties of the compound. Higher ratios of surfactant to active ingredient are some-times desirable, and are achieved by incorporationinto the formulation or by tank mixing.
Typical solid diluents are described in Watkins, et al., "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books, Caldwell, 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 dusts. Typical liquid diluents and solvents are de-scribed in Marsden, "Solvents Guide," 2nd Ed., rnter science, New York, 1950. Solubility under 0.1% is preferred for suspension concentrates; solution con-centrates are preferably stable against phase separa-tion at 0C. "McCutcheon's Detergents and Emulsifiers Annual~, MC Publishing Corp., Ridgewood, New Jersey, as well as Sisely and Wood, "Encyclopedia of Surface Active Agents", Chemical Publishing Co., Inc., New York, 1964, list surfactants and recommended uses.
All formulations can contain minor amounts of addi-tives to reduce foaming, caking, corrosion, microbio-l~gical growth, etc.
The methods of making such compositions are wellknown. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer or fluid energy mill. Suspensions are prepared by wet milling (see, for example, Littler, U.S. Patent 3,060,084). Granules and pellets may be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See J. E.
3s Browning, ~Agglomerationn, Chemical Enqineerinq, December 4, 1967, pp. 147ff. and "Perry's Chemical Engineer's Handbookn, 5th Ed., McGraw-Hill, New York, 1973, pp. 8-57ff.

For further information regarding the art of formulation, see for example:
H. M. Loux, U.S. Patent 3,235, 361, February 15, 1966, Col. 6, line 16 through Col. 7, line 19 and 5 Examples 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, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-1.64, 166, 167 and 169-182;
H. Gysin and E. Knusli, U.S. Patent 2,891,855, June 23, 1959, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4;
G. C. Klingman, "Weed Control as a Science", John Wiley & Sons, Inc., New York, 1961, pp. 81-96; and J. D. Fryer and S. A. Evans, "Weed Control Hand-bookn, 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103.
In the following examples, all parts are by weight unless otherwise indicated.
Example 9 Wettable Powder 2-11(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]amino-sulfonyllbenzeneacetic acid, methyl ester 80%
sodium alkylnaphthalenesulfonate2%
sodium ligninsulfonate 2%
synthetic amorphous silica 3%
kaolinite 13%
The ingredients are blended, hammer-milled until all the solids are essentially under 50 microns, re-30 blended, and packaged.

Example lO
Wettable Powder 2-t[~4,6-dimethylpyrimidin-2-yl)aminocarbonyl]amino-sulfonyl~benzeneacetic acid, methyl ester 50%
sodium alkylnaphthalenesulfonate 2%
low viscosity methyl cellulose 2%
diatomaceous earth 46%
The ingredients are blended, coarsely hammer-milled and then air-milled to produce particles essen-tially all below 10 microns in diameter. The product is reblended before packaging.
Example ll Granule Wettable Powder of Example 10 5%
attapulgite granules 95%
(U.S.S. 20-40 mesh; 0.84-0.42 mm) A slurry of wettable powder containing ~25%
solids is sprayed on the surface of attapulgite granules in a double-cone blender. The granules are dried and packaged.
Example 12 Extruded Pellet 2-ll(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-aminosulfonyl]benzeneacetic acid, methyl ester 25%
anhydrous sodium sulfate 10%
crude calcium ligninsulfonate 5%
sodium alkylnaphthalenesulfonate 1%
calcium/magnesium bentonite 59%
The ingredients are blended, hammer-milled and then moistened with about 12% water. The mixture is extruded as cylinders about 3 mm diameter which are cut to produce pellets about 3 mm long. These may be used directly after drying, or the dried pellets may be crushed to pass a U.S.S. No. 20 sieve (0.84 mm openings). The granules held on a U.S.S. No. 40 sieve (0.42 mm openings) may be packaged for use and the fines recycled.

~Z03536 Example 13 Oil Suspension 2-[l(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-aminosulfonyl]benzeneacetic acid, 5 methyl ester 25%
polyoxyethylene sorbitol hexaoleate 5%
highly aliphatic hydrocarbon oil 70%
The ingredients are ground together in a sand mill until the solid particles have been reduced to under about 5 microns. The resulting thick suspension may be applied directly, but preferably after being extended with oils or emulsified in water.
Exam~le 14 Wettable Powder 15 2-ll(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocar-bonyllaminosulfonyl]benzeneacetic acid, methyl ester 20%
sodium alkylnaphthalenesulfonate 4%
sodium ligninsulfonate 4%
low viscosity methyl cellulose~ ~ -~3~
attapulgite 69%
The ingredients are thoroughly blended. After grinding in a hammer-mill to produce particles essen-tially all below 100 microns, the material is re-blended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) and packaged.

.;1203536 Example 15 Low Strength Granule 2-1[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]amino-sulfonyl]benzeneacetic acid, ethyl ester 1%
N,N-dimethylformamide 9%
attapulgite granules 90%
(U.S.S. 20-40 sieve) The active ingredient is dissolved in the sol-vent and the solution is sprayed upon dedusted gran-ules in a double cone blender. After spraying of the solution has been completed, the blender is allowed to run for a short period and then the granules are pack-aged.
Example 16 Aqueous Suspension 2-t[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyll-aminosulfonyl]benzeneacetic acid, ethyl ester 40%
polyacrylic acid thickener 0.3%
dodecylphenol polyethylene glycol ether 0.5%
disodium phosphate 1%
monosodium phosphate 0.5%
polyvinyl alcohol 1.0%
water 56.7%
The ingredients are blended and ground together in a sand mill to produce particles essentially all under 5 microns in size.
~ le 17 Solution 2-t[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl~amino-sulfonyllbenzeneacetic acid, methyl ester, sodium salt 5%
water 95%
The salt is added directly to the water with stirring to produce the solution, which may then be packaged for use.

~ZC~3S36 ExamPle 18 Low Strength Granule 2-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]amino-sulfonyl]benzeneacetic acid, methyl ester 0.1%
attapulgite granules 99.9%
~U.S.S. 20-40 mesh) The active ingredient is dissolved in a solvent and the solution is sprayed upon dedusted granules in a double-cone blender. After spraying of the solution has been completed, the material is warmed to evapor-ate the solvent. The material is allowed to cool and then packaged.
Example 19 Granule 2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyll-aminosulfonyllbenzeneacetic acid, methyl ester 80 wetting agent 1%
crude ligninsulfonate salt (containing 10%
5-20% of the natural sugars) attapulgite clay 9%
The ingredients are blended and milled to pass through a 100 mesh screen. This material is then - -added to a fluid bed granulator, the air flow is ad-justed to gently fluidize the material, and a fine spray of water is sprayed onto the fluidized ma-terial. The fluidization and spraying are continued until granules of the desired size range are made.
The spraying is stopped, but fluidization is con-tinued, optionally with heat, until the water contentis reduced to the desired level, generally less than 1%. The material is then discharged, screened to the desired size range, generally 14-100 mesh ~1410-149 microns), and packaged for use.

Example 20 High Strength Concentrate 2-~[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-aminosulfonyl]benzeneacetic acid, methyl ester 99%
silica aerogel 0.5%
synthetic amorphous silica 0.5%
The ingredients are blended and ground in a hammer-mill to produce a material essentially all passing a U.S.S. No. 50 screen (0.3 mm opening). The concentrate may be formulated further if necessary.
Example 21 Wettable Powder 2-11(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocar-bonyl]aminosulfonyl]benzeneacetic acid, methyl ester 90%
dioctyl sodium sulfosuccinate 0.1%
synthetic fine siLica 9.9%
The ingredients are blended and ground in a hammer-mill to produce particles essentially all below 100 microns. The material is sifted through a U.S.S.
No. 50 screen and then packaged.
Example 22 Wettable Powder 2-1[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]amino-sulfonyllbenzeneacetic acid, ethyl ester 40%
sodium ligninsulfonate 20%
montmorillonite clay 40%
The ingredients are thoroughly blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in size. The material is reblended and then packaged.

~203536 Example 23 Oil Suspension 2-[~(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-aminosulfonyl]benzeneacetic acid, ethyl ester 35%
blend of polyalcohol carboxylic 6%
esters and oil soluble petroleum sulfonates xylene 59%
The ingredients are combined and ground together in a sand mill to produce particles essentially all below 5 microns. The product can be used directly, extended with oils, or emulsified in water.

lZ03536 Utility The compounds of the present invention are ac-tive herbicides. They have utility for pre- and/or post-emergence weed control in areas wh~re control of broadleaf weeds and certain grass, or other weeds is desired, such as around fuel storage tanks, ammunition depots, industrial storage areas, oil-well sites, drive-in theaters, around billboards, highway and railroad structures. By properly selecting rate and time of application, compounds of this invention may be used to modify plant growth beneficially, and also to selectively control weeds in crops such as whea~
and rice.
The precise amount of the compounds of Formula I
to be used in any given situation will vary according to the particular end result desired, the amount of foliage present, the weeds to be controlled, the soil type, the formulation and mode of application, weather conditions, etc. Since so many variables play a role, it is not possible to state a rate of application suitable for all situations. Broadly speaking, the compounds of this invention are used at levels of about 0.02 to 20 kg/ha with a preferred range of 0.1 to 10 kg/ha. In general, the higher rates of application from within this range will be selected for adverse conditions or where extended persistence in soil is desired.

lZ03536 `The compounds of Formula I may be combined with other herbicides and are particularly useful in combi-nation with the ureas: such as 3-t3,4-dichloroPhenYl)-l,l-dimethylurea (diuron); the~triazines: such as 2-chloro-4-~ethylamino)-6-(isopropylamino)-s-triazine (atrazine); the uracils: such as 5-bromo-3-sec-butyl-

6-methyluracil (bromacil); N-(phosponomethyl)glycine (glyphosate); 3-cyclohexyl-1-methyl-6-dimethylamino-s-triazine-2,4(lH,3H)-dione (hexazinone); N,N-dimethyl-2,2-diphenylacetamide (diphenamid); 2,4-dichlorophen-oxyacetic acid (2,4-D) (and closely related com-pounds); 4-chloro-2-butynyl-3-chlorophenylcarbamate (barban); S-(2,3-dichloroallyl)-diisopropylthiocar-bamate (diallate); S-(2,3,3-trichloroallyl-diiso-propylthiocarbamate (triallate); 1,2-dimethyl-3,5-diphenyl-lH-pyrazolium methyl sulfate (difenzoquat methyl sulfate); methyl 2-[4-(2,4-dichlorophenoxy)-phenoxy]propanoate (diclofop methyl); 4-amino-6-t _ -butyl-3-(methylthio)-1,2,4-triazin-5(4H)-one (metribuzin); 3-(3,4-dichlorophenyl)-1-methoxy-1-methylurea (linuron); 3-isopropyl-lH-2,1,3-benzo-thiodiazin-4(3~)-one-2,2-dioxide (bentazon); a,a,a_ trifluoro-2,6-dinitro-N,N-dipropyl-P-toluidine (trifluralin); 1,1'-dimethyl-4,4'-bipyridinium ion (para~uat); monosodium methanearsonate (MSMA);
2-chloro-2',6'-diethyl (methoxymethyl)acetanilide (alachlor); and 1,1-dimethyl-3-(~,a,~-trifluoro-m-tolyl)-urea (fluometuron).
The activity of these compounds was discovered in greenhouse tests. The tests are described and data resulting from'them are shown below.

lZ03536 Test A
Seeds of crabgrass (Digitaria spp.), barnyard-grass (Echinochloa crusgalli), wild oats (Avena fatua), cassia (Cassi~ tora), morningglory (IPomoea sp.), cocklebur (Xanthium spp.), sorghum, corn, soy-bean, rice, wheat and nutsedge tubers (Cyperus rotundus) were planted in a growth medium and treated pre-emergence with the chemicals dissolved in a non-phytotoxic solvent. At the same time, cotton having five leaves (including cotyledonary ones), bush beans with the second trifoliate leaf expanding, crabgrass and barnyardgrass with two leaves, wild oats with one leaf, cassia with three leaves (including cotyledonary ones), morningglory and cocklebur with four leaves (including the cotyledonary ones), sorghum and corn with three leaves, soybean with two cotyledonary leaves, rice with two leaves, wheat with two leaves, and nutsedge with three to five leaves were sprayed.
Treated plants and controls were maintained in a greenhouse for sixteen days, then all species were compared to controls and visually rated for response - to treatment.
The ratings, shown in Table A, are based on a numerical scale extending from 0 = no injury, to 10 =
complete kill. The accompanying descriptive symbols have the following meanings:
C - chlorosis/necrosis;
D - defoliation;
E = emergence inhibition;
G - growth retardation;
H = formative effects;
S s albinism;
U - unusual pigmentation;
6F s delayed flowering; and 6Y - flowerbuds abscised.

Compound 1 (~ S02-NH-C-NH--< 0~

10 ComPound 2 ~ S02-NH-C-NH--( O ~

ComPound 3 ~_ O N_~ -<O )--S02-NH-C-NH _~ 0 --~ N--~

ComPound 4 ~ O N--NH-c-NH--~ 0~

lZ03536 Compound 5 (~ S02-NH-C-NH ~ O N

Compound 6 SO2-NH-C-NH ~ O N

`Compound 7 (~ S02-NH-C-NH~

ComPound 8 . O N
<~ S02-NH-C-NH--< 0~
N---~

ComPound 9 ~ S02-NH-C-NH--~

CH2COOCH (CH3) 2 CH3 10 Compound 10 O N~
~ So2-NH-c NH--< O~
lS CH2COOCH(CH3) 2 OCH3 Coml~ound 11 . OCH3 ~ O N~

2 5 CH 2COOH OCH 3 .

ComPound 12 (~ S02-NH-C-NH--< 0~

~Z035~6 Compound 13 Compound 14 ~ SO2-NH-C-NH ~ O N

ComPound 15 ~ SO2-NH-C-NH ~ O N

lZ03536 Table A

Compound Compound Compound Compound s Rate kg/ha .05 0.4 0.4 0.4 POST-EMERGENCE
Bush bean 9C 9C 9D,9G,6Y 9D,9G,6Y
Cotton 5C,9G 3C,9G 2U,6C,9G 10C
Morningglory 3C,8H 9C 5C,9G 9C
Cocklebur 5C,9H 9C 5C,9G 5C,9H
Cassia 6C,9G 3C,7G 2C,6G 5C,9G
Nutsedge 3C,9G lC 9G 3C,9G
Crabgrass 4G 0 10C 9C
Barnyardgrass 4G . lC,2H 3C,9H 9C
Wild Oats 0 0 6C,9G 5C,9G
Wheat 0 0 9C 6C,9G
Corn 2C,8H 0 lC,9G 5U,9G
Soybean 2C,9G 10C 2C,8G 9C
Rice 5C,9G 2G 4C,9G 9C
Sorghum 9G 3G 9C 5U,9C
PRE-EMERGENCE
Morningglory 9G 9G 5C,9G 9C,9G
Cocklebur 9H 9H 9H 9H
Cassia 8G 8G 9G lC,9G
Nutsedge 10E 2G 10E 10E
Crabgrass SG lC lC,7G 2C,9G
Barnyardgrass 3C,SG 3C 2C,9H 3C,9H
Wild Oats 6G 0 SC,9H 3C,9H
Wheat 5G 0 9H 9H
Corn 8G 7G 9H - 10H
Soybean lH 7H 8H 8H
Rice 10E 9H 10E 10E
: Sorghum 9G 6G 10H SC,9H

~ .

ss Table A (continued?

Compound Compound Compound Compound S
Rate kg/ha .05 .05 0.4 0.4 POST-EMERGENCE
Bush bean 9D,9G, 6Y 9C 7C,9G 6C,9G
Cotton 4C,9G 5C,9G 5C,9G 5C,9G
Morningglory 9C 10C 3C,8H 9C
0 Cocklebur 9C 10C 9C 9C
Cassia 3C,5G 5C,9G 9C 5C,8G
Nutsedge 0 0 2C,8G 7G
Crabgrass lC 0 2C 2C,5G
Barnyardgrass lC lC 2C,5H 3C,9H
Wild Oats 0 0 . lC 2C,SG
Wheat 0 0 0 lC,SG
Corn lC 2C,5H 2C,6H 2U,9G
Soybean 5C,8G 5C,9G 6C,9G 6C,9G
Rice lC,4G lC,6G 3C,8G 5C,9G
Sorghum 0 lC,6G 2C,8H 2C,8G
PRE-EMERGENCE
Morningglory 9G 5C,9G 7G 9G
Cocklebur 9H 9H 9H 9H
~ 20 -~Ca~ssia 8G-- ~~ ~ 3C,8G 2C,8G 8G
Nutsedge 8G 10E 10E 10E
Crabgrass 3G - 2G lC 3G
Barnyardgrass lC lC 2C,6H 2C,8H
Wild Oats 0 lC 3G 8G
Wheat 0 2G 0; 8G
Corn lC,6G lC,8G 2C,8G 2C,9G
Soybean 2C,3H 2C,5H 0 lC,3H
25 Rice SG lC,?G 10E 10E
Sorghum - lC,4G 2C,9H 2C,9G 5C,9H

,~

lZC~;~S36 Table A (continued) Compound Compound Compound Compound .05 0.4 0.4 0.4 POST-EMERGENCE
Bush bean lC,6Y 4C,7G,6Y 9C 2H,6F
Cotton ~ 2C 2C,2H 4C,8G lH
Morningglory 3B,8G 0 lC 0 Cocklebur 3C,6G 2C,6G 3C,9G 0 Cassia 2C 2C 3C,SG 0 Nutsedge lC 0 4G 0 Crabgrass 0 0 2C 0 8arnyardgrass 0 0 lC,5G lC
Wild Oats 0 0 0 0 Wheat 0 Corn 0 0 lC 0 15 Soybean lC 0 lC,3H 0 Rice 0 2G 5G 2C
Sorghum lC lC . lC,SH lC
PRE-EMERGENCE
Morningglory 2C,5G 0 6G 0 Cocklebur 2C,5G SH 8H 0 20 Cassia lC 4G 2C,5G 0 Nutsedge 10E 0 9G 0 Crabgrass 2G 0 2C 0 8arnyardgrass 2G 2G 3C lC
Wild Oats 0 0 j lC 0 Wheat 0 0 i lC 0 Corn 2C,2G 2C,4G 3C,6H 0 Soybean 0 lC 2C 0 25 Rice 2C lC,SG 9H 0 Sorghum 2G 4G 2C,8H 0 Table A (continued) Compound Compound Compound 0.4 0.4 0.4 POST-EMERGENCE
Bush bean 4C,7G,6Y 9C 4S,5G,6Y
Cotton 2C,3H 5C,9G 4C,7G
Morningglory lC 9C 2C,5G
10 Cocklebur lC 10C 2C
Cassia 3C 4C,8G 2C
Nutsedge 0 3G 0 Crabgrass 2C lC 0 Barnyardgrass 3C,7H 2C,6H 0 Wild Oats 3G 0 0 Wheat 2G 0 0 Corn 2C,6H 2C,9H 0 15 Soybean 3C,5G 9C 2C
Rice 2C,6G lC,3G 0 Sorghum 2C,7H 2C,5G 0 PRE-EMERGENCE
Morningglory 8G 9G SG
Cocklebur 5H 9H 0 20 Cassia -- -- 5G 5C,8G 0 Nutsedge 3G 8G 10E
Crabgrass lC 0 lC
Barnyardgrass 2C,7H 2G lC
Wild Oats 8G 0 0 ~-Wheat SG 0 0 Corn 2C,7G 2C,6G lC
Soybean lC,lH 2C,6H 0 25 Rice 2C,8G lC,3G 0 Sorghum 2C,8H 2C,8H 0 lZ03536 Test B
Two plastic bulb pans were filled with ferti-lized and limed Fallsington silt loam soil. One pan was planted with corn, sorghum, Kentucky bluegrass and several grassy weeds. The other pan was planted with cotton, soybeans, purple nutsedge (cYperus rotundus), and several broadleaf weeds. The following grassy and broadleaf weeds were planted: crabgrass (Diqitaria sanguinalis), barnyardgrass (Echinochloa crusgalli), wild oats (Avena fatua), johnsongrass (Sorghum hale-pense), dallisgrass (PasPalum dilatatum), giant fox-tail (Setaria faberii), cheatgrass (Bromus secalinus), mustard (Brassica arvensis), cocklebur (Xanthium Pensvlvanicum)~ pigweed (Amaranthus.retroflexus), morningglory (IPomoea hederacea), cassia (Cassia tora), teaweed (Sida spinosa), velvetleaf (Abutilon theophrasti), and jimsonweed (Datura stramonium). A
12.5 cm diameter plastic pot was also filled with pre-pared soil and planted with rice and wheat. Another 12.5 cm pot was planted with sugarbeets. The above four containers were treated pre-emergence with several test compounds within the scope of the invention.
Twenty-eight days after treatment, the plants were evaluated and visually rated for response to the chemical treatments utilizing the rating system de-scribed previously for Test A. The da~a are summar-ized in Table B.

., .

`:
lZ03536 Table B

PRE-EMERGENCE ON FALLSINGTON SILT LOAM
s Compound 1 Compound 2 Compound 3 Rate kg/ha 0.06 0.25 0.25 0.12 Crabgrass 0 0 0 0 10 Barnyardgrass 2G 3G 0 3G
Sorghum 7G,5H 7G,5H 2G 0 Wild Oats 0 0 0 0 Johnsongrass 0 0 0 0 Dallisgrass 0 0 0 0 Giant foxtail 0 3G 0 0 Ky. bluegrass 0 4G 0 0 Cheatgrass 0 3G 0 0 15 Sugarbeets 0 7G 0 3G
Corn 0 Mustard 7G,3C 8G,6C 5G 4G
Cocklebur 5G 7G,3H 0 0 Pigweed 0 8G,8C 3G 3G
Nutsedge 4G 8G 0 0 Cotton 4G 5G,3H 0 0 20 Morningglory 3G 6G 0 0 Cassia 0 SG 3G 4G
Teaweed 0 0 3G 0 Velvetleaf 3G 6G,SH 3G 0 ~~ ~imsonweed 0 4G 0 0 Soybean 0 0 2G 0 Rice 4G 5G 0 0 Wheat 0 0 0 0 ~Z03536 Table B (continued) PRE-EMERGENCE ON FALLSINGTON SILT hOAM

Compound 4 Compound 8 Rate kg/ha 0.03 0.12 0.06 0.25 Crabgrass 0 2G 0 3G
Barnyardgrass 2G 5G 3G 5G,3C
Sorghum 3G,2H 9G,5H 8G,SH 9G,SH
10 Wild Oats 2G 4G . 4G 7G
Johnsongrass 0 5G,3H 5G,3H SG,5H
Dallisgrass 0 3G 3G 0 Giant foxtail 0 3G 3G,3H 7G,3H
Ky. bluegrass 0 2G 4G 7G,3H
Cheatgrass 3G 4G 5G,3C 7G,3C
Sugarbeets SG 7G,3H 8G,9C 10C
Corn 0 2G 3G,2C 6G~2H
Mustard 8G,8C 8G,8C 9G,9C 10C
Cocklebur 0 3G 6G,3H 9G,9C
Pigweed 7G 8G SG,3C 10C
Nutsedge 0 0 7G 8G
Cotton - 3G SG,3H 3H SH
Morningglory 3G 6G 6G,SH 6G,SH
Cassia 4G 4G 4G 7G
Teaweed 0 3G 2G SG
20 . Velvetleaf 4G,3H 6G,SH 5G,3H 7G,8C
Jimsonweed 0 5G,SC 6G,4C 7G,7C
Soybean 2G . 0 2G SG,3H
Rice 4G 6G 7G,3H 8G,5H
Wheat 0 0 3G SG

~Z0353 6s Test C
The test chemicals, dissolved in a non-phyto-toxic solvent, were applied in an overall spray to the foliage and surrounding soil of selected plant spe-cies. One day after treatment, plants were checkedfor rapid burn injury. Approximately fourteen days after treatment, all species were visually compared to untreated controls and rated for response to treat-ment. The rating system was as described previously for Test A. The data are presented in Table C.
All plant species were seeded in Woodstown sandy loam soil and grown in a greenhouse. The following species were grown in soil contained in plastic pots (25 cm diameter by 13 cm deep): soybeans, cotton, alfalfa, corn, rice, wheat, sorghum, velvetleaf (Abutilon theophrasti), sesbania (Sesbania exaltata), Cassia (Cassia tora), morningglory (IPomoea heder-acea), jimsonweed (Datura stramonium), cocklebur (Xanthium ensYlvanicum), crabgrass (Diqitaria spp.), nutsedge (cYPerus rotundus), barnyardgrass (Echino-chloa crusqalli), giant foxtail (Setaria faberii) and wild oats (Avena fatua). The following 5pecies were grown in soil in a paper cup (12 cm diameter by 13 cm deep): sunflower, sugarbeets, and mustard. All plants were sprayed approximately 14 days after planting. Additional plant species are sometimes added to this standard test in order to evaluate unusual selectivity.

~5;36 Table C

Over-the-Top Soil/Foliage Treatment Compound 2 Rate kg/ha 0.06 0.25 Soybeans 3G,lC 6G,3C
Velvetleaf 9G,4C 10G,8C
Sesbania 9G,3C 10G,6C
Cassia 10G,3C 10G,8C
Cotton 8G,3C 9G,4C
Morningglory 10G,4C 10C
Alfalfa lC lC
Jimsonweed lC 3G,lC
Cocklebur 9G,3C 10G,5C
Corn 0 15 Crabgrass 0 0 Rice SG SG
Nutsedge Barnyardgrass 0 0 Wheat 0 0 Giant foxtail 0 lG
Wild Oats 0 lC
20 Sorghum 0 0 ~203536 Test D
A test sample of compound 2 was formulated and applied directly to the water ~f simulated paddies, three days after transplanting of rice. The paddies 5- were maintained in a greenhouse, and plant response ratings were taken one week and four weeks after application.
Water Rate, Rice Barnyardgrass* Chestnut* Arrowhead*
kg ai/ha 1 wk. 4 wks. 4 weeks 4 weeks _ 4 weeks 0.125 0 0 0 8G 0 0.5 0 0 0 lOC 6G

* Echinochloa sp., Eleocharis sp., and Saqittaria sp., respectively.

Reference to the table above indicates that rice tolerated the application of the test sample at 500 g ai/ha, whereas the important weed (in rice culture in some areas) water chestnut was completely controlled.
Arrowhead, which also is an important weed in some rice culture areas, was partially controlled at the same application rate.

Claims (20)

WHAT IS CLAIMED IS:

1. A compound of the formula:

wherein L is CO2R10, CONR3R4 or CN;
R is H, F, Cl, Br, NO2, CF3, C1-C3 alkyl or C1-C3 alkoxy;
R1 is H or C1-C4 alkyl;
R2 is H or CH3;
R3 is H, C1-C4 alkyl or OCH3;
R4 is H or C1-C4 alkyl;
R3 and R4 can be taken together to form -(CH2)4-, -(CH2)5 or -(CH2CH2)2O;
R8 is H, CH3 or OCH3;
R10 is H, C1-C4 alkyl, C3-C4 alkenyl, CH2CH2Cl or CH2CH2OCH3;
A is , or W is O or S;
X is H, Cl, Br, CH3, CH2CH3, C1-C3 alkoxy, CF3, SCH3 or CH2OCH3;
Y is CH3 or OCH3;

Z is N, CH, CCl, CBr, CCN, CCH3, CCH2CH3, CCH2CH2Cl or CCH2CH=CH2;
Y1 is H, CH3, OCH3 or OCH2CH3;
and Q is O or CH2;
and their agriculturally suitable salts;
provided that:
(1) when L is CONR3R4, then Z is CH or N;
(2) when R3 is OCH3, then R4 is CH3; and (3) when W is S, R8 is H.

2. A compound of Claim 1 wherein L is CO2R10, W is O, Z is N, CH, CCl, CBr or CCH3, and R8 is H or CH3.

3. A compound of Claim 2 wherein Z is CH or N, X is CH3 or OCH3, and R1 and R2 are H.

4. A compound of Claim 3 wherein A is , R8 is H and R is H.

5. A compound of Claim 4 wherein R10 is CH3 or CH2CH3.

6. The compound of Claim 1, 2-[[(4,6-dimethoxy-pyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzeneace-tic acid, methyl ester.

7. The compound of Claim 1, 2-[[(4,6-dimethyl-pyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzeneace-tic acid, methyl ester.

8. The compound of Claim 1, 2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]ben-zeneacetic acid, methyl ester.

9. The compound of Claim 1, 2-[[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]benzene-acetic acid, methyl ester.

10. The compound of Claim 1, 2-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]-benzeneacetic acid, methyl ester.

11. The compound of Claim 1, 2-[[(4,6-dimethoxy-pyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzeneace-tic acid, ethyl ester.

12. The compound of Claim 1, 2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]ben-zeneacetic acid, ethyl ester.

13. A method for controlling the growth of un-desired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 1.

14. A method for controlling the growth of un-desired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 2.

15. A method for controlling the growth of un-desired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 3.

16. A method for controlling the growth of un-desired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 4.

17. A method for controlling the growth of un-desired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 5.

18. A method for controlling the growth of un-desired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 6.

19. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Claim 7.

20. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of the compound of Claim 8.