IE44983B1 - Pyrimidine and triazine derivatives and their use as herbicides and plant growth regulants - Google Patents

Abstract

Process for the preparation of N- (heterocycloaminocarbonyl) sulfonamides with herbicidal properties, having the general formula I: (see form in desc.) Wherein R represents: (see form in desc.) R1 represents one of the radicals: (see form . R3 and R6 represent, independently of each other, hydrogen, fluorine, chlorine, chlorine, bromine, iodine, alkyl having 1 ... 4 carbon atoms, alkoxy having 1 ... 4 carbon atoms, nitro , trifluoromethyl, cyano, CH 3 S (O) n- or CH 3 CH 2 S (O) -; R 4 represents hydrogen, fluorine, chlorine, bromine, or methyl; R 5 represents hydrogen, fluorine, chlorine, bromine, methyl, or methoxy, R 7 represents hydrogen, fluorine, chlorine, bromine, alkyl of 1 to 2 carbon atoms or alkoxy of 1 to 2 carbon atoms; R3 represents hydrogen, methyl, chlorine or bromine; Rg and R10 represent, independently of one another, hydrogen, methyl, chlorine or bromine; W and Q independently represent oxygen or sulfur; n represents 0.1 or 2; X independently represents oxygen or sulfur; n represents hydrogen ......

Description

This invention relates to N-(heterocyclic aminocarbonyl)aryl sulfon amide agricultural chemicals. 4&083 ' French Patent No. 1,468,747 discloses the following para-substituted phenylsulfonamides, useful as anti diabetic agents: /~v ? jTX R~V_/ SVNH”C'NH \_/ wherein R=H, halogen, CF3 or alkyl.

Logemann et al. Chem. Ab’., 53, 18052 g (1959), disclose a number of sulfonamides, including uracil derivatives and those having the formula: jTV If H3c—f V—S02NHCNHR wherein R is butyl, phenyl or and Rj 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 and phenyl were most potent. The others were of low potency or inactive. h 15 Wojciechowski, J. Acta. Polon. Pharm. T9, p. 121—5 (1962) {Chem. Ab., - 2 - ^40Q3 59, 1533 e} describes the synthesis of N~{2,6-dimethoxypyrimidin-4~yl)-ami nocarbonyl}-4-methylbenzenesulfonarai de: 0CH3 CH3- \=/ \ J och3 Based upon similarity to a known compound, the author predicted hypogly-5 cemic activity for the foregoing compound.

Netherlands Patent 121,788, published September 15, 1956, teaches the preparation o* compounds of Formula (i), and their use as general or selective herbicides, Ν'/' /OWL —N ^ ^NHRi r3 10 wherein Ri and R2 may independently be alkyl of 1—4 carbon atoms; and R3 and Ri* may independently be hydrogen, chlorine or alkyl of 1—4 carbon atoms.

Compounds of Formula (ii), and their use as anti diabetic agents, are 15 reported in _J. Drug Res. 6, 123 (1974) - 3 - (11) 4 49 β Q\ f i S02NHCNHR wherein R is pyridyl.

The presence of undesired vegetation causes substantial damage to-useful crops, especially agricultural products that satisfy man’s basic 5 food and fiber needs, such as cotton, rice, corn, wheat or soybean. The current population explosion and concomitant world food and fiber shortage demand improvements in the efficiency of producing these crops. Preventing or minimizing the loss of a portion of suth valuable crops by killing or inhibiting the growth of undesired vegetation is one way of improving this 10 efficiency.

A wide variety of materials useful for killing or inhibiting (controlling) the growth of undesired vegetation is available; such materials are commonly referred to as herbicides. However, the need exists for still more effective herbicidek that destroy or control weeds without causing 15 significant damage to useful crops.

Some weeds (nutsedge is a particular example) are very difficult to control; many of the herbicides that are used to control nutsedge are so nonselective that they cause damage to the crops themselves.

According to this iiivendon,there are provided novel compounds of 20 Formula I and their agriculturally suitable salts, suitable agricultural compositions containing them, and methods of using them as selective, as well as general herbicides having both preemergence and postemergence activity. These compounds are highly active herbicides. They are especially useful -4 - 4 4 0 8 3 in controlling nutsedge, yet cause minimal damage to desired crops, such as cotton, rice, corn or wheat.

W 11 I.

Rx—SO2—NH—C—NH—R wherein X ΪΙ3 n .· /Λ /. 77 R is-/ ) or -V N > Ri is “C y-"Rg V=/ )—( 1 Z R? X ' £V M · C0: Re Rg Rio ^ R3 and R6 are independently hydrogen, fluorine, chlorine, bromine, iodine, alkyl of 1—4 carbon atoms, alkoxy of 1—4 carbon atoms, nitro, trifluoro* methyl, cyano, CH3S(0)n— or CH3CH2S(0)n—; Ru is hydrogen, fluorine, chlorine, bromine or methyl; 10 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 R10 are independently hydrogen, methyl, chlorine or bromine; 15 U 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 - 5 - 44983 atoms, trifluoromethyl, €H3S— or CH30CH2—; and Z is methyl or methoxy; or their agriculturally suitable salts; provided that: a) when R5 is other than hydrogen, at least One of R3, R^, Re and 5 R7 is other than hydrogen and at least two of R3, Rj,, R6 and R7 must be hydrogen; b) when R5 is hydrogen and all of R3, Ri*, Re and R7 are other than hydrogen, than all of R3, Ri,, R6 and R7 must be either chlorine or methyl; and 10 c) when R3 and R7 are both hydrogen, at least one of Ru, R5 or Rs must be hydrogen.

Preferred in orddr of1 increasing preferance based on activity or cost or both are 1) those compounds of Formula I, defined above, wherein Ri is R3 A ;^R5; iR7 r6 2) compounds of preferance 1) wherein R3 is hydrogen, fluorine, chlorine, bromine, alkyl of 1—4 carbon atoms, alkoxy of 1—4 carbon atoms, CH3S— or CH3CH25—; and R5 is hydrogen, fluorine, chlorine, bromine or methyl; and 20 R6 is hydrogen, fluorine, chlorine, bromine, alkyl of 1—4 carbon atoms, alkoxy of 1—4 carbon atoms, trifluoromethyl, nitro, CH3S— or - 6 - 440s3 CH3CH2S—; provided that: a) when R5 is other than hydrogen, R3,' Rt,, R6 or R7 must independently be hydrogen, fluorine, chlorine, bromine, methyl or methoxy; 5 3) compounds of preference 2) wherein a) R is said pyrimidinyl radical; X is methyl or alkoxy having 1—3 carbon atoms; and Z is methyl or methoxy; or b) R is said triazinyl radical; 10 X is methyl or alkoxy of 1—3 carbon atoms; and Z is methoxy; 4) compounds of preference 3} wherein R3 is hydrogen, fluorine, chlorine, bromine, alkyl of 1—2 carbon atoms, alkoxy of 1—2 carbon atoms, CH3S— or CH3CH2S—; and 15 R^, R5 and R? are independently hydrogen, fluorine, chlorine or methyl; and Rg is hydrogen, fluorine, chlorine, bromine, alkyl of 1—2 carbon atoms, alkoxy of 1—2 carbon atoms, trifluoromsthyl, nitro, CH3S—, or CH3CH2S—; 20 5} compounds of preference 3} wherein R3, R4, R5, R6 and R7 are independently hydrogen, fluorine, chlorine or methyl; 6) compounds of preference 3) wherein R3 is fluorine, chlorine or methyl; and 25 R^, R5, Rs and Ry are independently hydrogen, fluorine, chlorine or methyl; provided that: - 7 - 44983 when R5 is other than hydrogen, Ri* and R6 must be hydrogen; 7) compounds of preference 3) wherein R3 is fluorine, chlorine or methyl; and 1 Ri, and R6 are hydrogen; and 5 R5 and R7 are independently hydrogen, fluorine, chlorine or methyl; 8) compounds of preference 3) wherein R3 is hydrogen, fluorine, chlorine, bromine, alkyl of 1—4 carbon atoms, alkoxy of 1—4 carbon atoms, CH3S—, or CH3CH2S—; and Ri,, R5 and R7 are hydrogen; and 10 Rg is hydrogen, fluorine, chlorine, bromine, alkyl of 1—4 carbon atoms, alkoxy of 1—4 carbon atoms, trifluoromethyl, nitro, CH3S— or CH3CH2S; 9) compounds of preference 8) wherein R3 is fluorine, chlorine, bromine, alkyl of 1—2 carbon atoms or 15 alkoxy of 1—2 carbon, atoms; and R6 is hydrogen, fluorine, chlorine, bromine, alkyl of 1—2 carbon atoms, alkoxy of 1—2 carbon atoms, trifluoromethyl or nitro; and 10) compounds of preference 8) wherein R3 is fluorine, chlorine, bromine, methyl or methoxy; and 20 Re is hydrogen, fluorine, chlorine, bromine, methyl, methoxy or nitro.

Also, preferred in. order of increasing preference based on activity or cost or both are: A) those compounds of Formula I, defined above, wherein y^~\\ or / C Ri is Ra Q R, S ^ *9 D K10* - 8 - B) compounds of preference A) wherein (a) R is said pyrimidinyl radical; Q is sulfur; X is methyl or alkoxy or 1—3 carbon atoms; and Z is methyl or methoxy; and (b) P, is said triazinyl radical; 0 is sulfur; 4<}983 t X is methyl or alkoxy of 1—3 carbon atoms; and Z is methoxy; S C) compounds of preference A) wherein Rj is and R8 is hydrogen.

Re Similarly, preferred based on activity are those compounds of Formula 1, defined aboye, wherein 1) Ri is ; and W is oxygen.

Specifically, preferred for their outstanding activity or highly favorable cost or both are: 1) N - 1(4 - methoxy - 6 - methylpyrimidin - 2 - yl) ami nocarbonyl}-2 - chlorobenzenesulfonamide, m.p. 194—196°C; 2) N - {{4,6 - dimethoxypyrimidin - 2 - yliaminocarbonyl} - 2,5 - dicbloro- 15 benzenesulfonamide, m.p. 189—190°C; 3) N - {(4 - methoxy - 6 - methylpyrimidin - 2 - yl)ami nocarbonyl} - 2-methylbenzenesulfonamide, m.p. 172—174°C; and 4) N - {(4,6 - dimethylpyrimidin - 2 - yl)aminocarbonyU - 2 - thiophene-sulfonamide, m.p. 224—228°C. 5) N - {(4 - methoxy - 6 - methyl - 1,3,5 - triazin - 2 - yl)aminocarbonyl}- 2 - chlorobenzenesulfonamide, m.p. 174—178°C; - g . 44983 6) N - {(4,6 - dimethoxy - 1,3,5 - triazin - 2 - yl)aminocarbony1}-2-chlorobenzenesulfonamide, m.p. 188—189°C; and 7) N - {(4,6 - dimethoxy - 1,3,5 - triazin - 2 - yl)aminocarbonyl}- 2,5-dimethoxybenzenesulfonamide, m.p. 187—188°C.

While all of the compounds of Formula I are herbicidal, not all of them are selective on all crops. However, by selecting particular compounds, weed control and crop safety can be obtained. Thus, some compounds show particular selectively for control of weeds in wheat and rice; nut-sedge control in crops such as corn, cotton, soybeans, or rice; brush 10 control; and water hyacinth control. In addition, the compounds of Formula I are useful plant growth regulants, e.g. increasing sugar content in sugarcane and sorghum and suppressing seedhead formation in grasses such as Bahia grass.

Specifically, preferred 15 A) for selective control of weeds in wheat are: 1) N - {(4 - methoxy - 6 - methylpyrimidin - 2 - yl)ami nocarbonyl} - 2-chloro - 5 - methoxybenzenesulfonamide, m.p. 199—200°C; 2) N - {(4 - methoxy - 6, - methyl - 1,3,5 - triazin - 2 - yl)aminocarb-onyl} - 2 - chlorobenzenesulfonamide, m.p.174—178°C; 20 3) N - {(4,6 - dimethoxy - 1,3,5 - triazin - 2 - yl)ami nocarbonyl} - 2- chlorobenzenesulfon'amlde, m.p. 188—189°C; and 4) N - {(4,6 - dimethoxy1- 1,3,5 - triazin - 2 - yl)aminocarbonyl} - 2,5-dimethoxybenzeneSulfofiamide, m.p. 187—188°C.

B) for their selective control of nutsedge in crops are: - 10 - *4883 1) N - ί(4,6 - dimethoxypyrimidin - 2 - yl)aminocarbotnyl} - 2,5 - dichi orobenzenesulfonamide, m.p. 189—190°C; and 2) N - {(4,6 - dimethylpyrimidin - 2 - yl)aminocarbonyl} - 2,6 - di-chlorobenzenesulfonamide, m.p. 177—182°C; 5 C) for water hyacinth control are: 1) N - {4 - methoxy - 6 - methylpyrimidin - 2 - yl)ami nocarbonyl) - 2-chlorobenzenesulfonamide, m.p. 194—196°C; 2) N-{(4 - methoxy - 6 - methyl - 1,3,5 - triazin - 2 - yl)ami nocarbonyl}-2 - chlorobenzenesulfonamide, m.p. 174—178°C; 10 3) N - {(4,6 - dimethoxy - 1,3,5 - triazin - 2 - yl)aminocarbonyl)- benzenesulfonamide, m.p. 183—185°C; and 4) N -{(4 - methoxy - 6 - methyl - 1,3,5 - triazin - 2 - yl)ami nocarbonyl}-2 - chloro - 5 - methoxybenzenesulfonamide, m.p. 175—176°C; D) for growth regulant use are: 15 1) N-{4,6 - dimethylpyrimidin - 2 - yl)aminocarbonyl} - benzenesulfon- amide; m.p. 228—230°C; and 2) N - {4,6 - dimethoxypyrimidin - 2 - yl)ami nocarbonyl} - 2,5 - di-chlorobenzenesulfonamide, m.p. 189—190°C. 3) N - {(4,5 - dimethoxy - 1,3,5 - triazin - 2 - yl)ami nocarbonyl)- 20 benzenesulfonamide, m.p. 183—185°C; 4) N - {(4 - methoxy - 6 - methyl - 1,3,5, - triazin - 2 - yl)amino-carbonyl}benzenesulfonamide; 5) N - {(4,6 - dimethyl - 1,3,5 - triazin - 2 - yl)aminocarbonyl)-benzenesulfonamide, m.p. 200—201°C; and 25 6) N - {(4 - methoxy - 6 - methyl - 1,3,5 - triazin - 2 - yl)amino- carbonyl) - 2 chlorobenzenesulfonamide, m.p. 174—178°C. - Π - 44S®3 Ε) for selective control of weeds in rice are: 1) N - {(4 - methylpyrimidin - 2 - yl)ami nocarbonyl} - 2 - chloro- * benzenesulfonamide; m.p. 201—203°C; and 2) N - {(4,6 - dimethoxypyritnidin - 2 - yl) ami nocarbonyl} - 2,5 - di- 5 bromobenzenesulfonamide; m.p. 201—204°C.

F) for selective control of brush is: 1) N - {(4,6 - dimethoxy - 1,3,5 - triazin - 2 - yl)aminocarbonyl} -benzenesulfonamide, m.p.'183—185°C; Synthesis.

As shown in Equation 1, the compounds of Formula I can be prepared by reacting an appropriate 2-ami no-pyrimidine or 2-amino-l,3,5-triazine of Formula III with an appropriately substituted sulfonyl isocyanate or isothiocyanate of Formula II; Ri, W, X, 1 and R being as previously defined.

Equation!.

W II RiSOjNCW + NH2—R R1S0ZNHCNH—R (II) ' (ill) (I) The reaction is best carried out in inert aprotic organic solvents such as methylene chloride, 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 or isothiocyanate 20 to a stirred suspension of amine III. Since such isocyanates and isothiocyanates usually are liquids, their addition can be easily controlled. The reaction is generally exothermic. In some cases, the desired - 12 - product is insoluble in the warm reaction medium and crystallizes from it in pure form. 4*2983 Products soluble in the reaction medium are isolated by evaporation of the solvent, trituration of the solid residue with solvents such as 1-5 chlorobutane or ethyl ether, and filtration.

In certain cases, it is possible to obtain an isomeric product from the reaction shown in Equation 1. Such isomeric products would result from addition of compound II to the endocyclic nitrogen atoms of amine III and have a structure as exemplified below: Η μ NH I V W 11 V / \ R1-S02NHC-N''N R1S02NHC-N yx, R1S02NHC-N y—I or I |i W W zAn-\ 1 * It is to be understood that reaction products resulting from the addition of a compound of Formula II to the exocyclic as well as the endocyclic nitrogen atoms of the amines III are to be considered a part of this invention. Such products in general exhibit activities of the same 15 types as the compounds of Formula I.

The intermediate sulfonyl isocyanates of Formula II (wherein W is 0) can be prepared by reacting corresponding sulfonamides with phosgene in the presence of n-butyl isocyanate at reflux in a solvent such as chlorobenzene, according to the procedure of H.Ulrich and A. A. Y. Sayigh, 20 Newer Methods of Preparative Organic Chemistry, Vol. VI p 223—241, - 13 - Acedemic Press, New York and London, W. Foerst Ed, In cases where the desired sulfonyl isocyanate Is formed in low yield using the above procedure, the sulfonyl urea formed by reaction of butyl isocyanate with the appropriate sulfonamide can be reacted with phosgene as described in 5 the above reference.

The preparation of sulfonamides from ammonium hydroxide and sulfonyl chlorides is widely reported in the literature, e.g. Crossley et al., Certain sulfonyl chlorides are best prepared by chlorosulfonation of a substituted benzene, naphthalene, or thiophene in carbon tetrachloride according to the teaching of Η. T. Clarke et al. On. Synth. Coll. Vol. 1, 2nd Ed. 1941, p 85. Other benzenesulfonyl chlorides are best made by diazotization of the appropriate aniline with sodium nitrite in HC1, foil-15 owed by reaction of the diazonium salt with sulfur dioxide and cuprous chloride in acetic acid according to the teaching of H. L. Yale and F. Sowinski, £. Org. Chem. 25 1824 (1960).

Furansulfonylchlorides are best prepared as shown in Equation 2. Equation 2.

O+ "-BuLi ry,· —> 0^ ^ -30°c - 14 - 44983 Sulfonyl isothiocyanates can be prepared by treatment of sulfonamides with carbon disulfide and potassium hydroxide followed by reaction of the dipotassium salt with phosgene according to the teaching of K. Hartke, Arch. Pharm,, 299, 174 (1966).

The synthesis of heterocyclic amine derivatives has been reviewed in "The Chemistry of Heterocyclic Compounds", a series published by Interscience Pub!., New York and London. 2-Ami nopyrimidines are described by D.J.Brown in "The Pyrimidines", Vol, XVI of the above series.

Agriculturally suitable salts of compounds of Formula I are also use-10 ful herbicides and can be prepared by 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 & 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 quaternary amine salt) with a solution containing the cation to be exchanged. This method is most effective when the desired 20 salt containing the exchanged cation is insoluble in water and can be separated by filtration.

Exchange may also be effected by passing an aqueous solution of a salt of a compound of Formula I (e.g. an alkali metal or quaternary amine salt) through a column packed with a cation exchange resin containing the 25 cation to be exchanged. In this method, the cation of the resin is ex- - 15 - 44983 changed 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.

Acid addition salts, useful in this invention, can be obtained by 5 reacting a compound of Formula I with a suitable acid, e.g. £-to1uene-sulfonic acid or trichloroacetic acid.

The compounds of this invention and their preparation are further illustrated by the following examples wherein temperatures are given in degrees centigrade. The term "ethyl ether" refers to diethyl ether.

EXAMPLE 1 N-{(4,6-Dimethylpyrimidin-2-yl)ami nocarbonyl}benzenesulfonamide To a dry, well-stirred mixture of 12.4 g of 2-ami no-4,6-dimethyl-pyrimidine in 250 ml of methylene chloride at ambient temperature and pressure was added dropwise 18.3 g of benzenesulfonyl isocyanate. The 15 resulting mixture was stirred for two hours and the precipitated product removed by filtration. After being washed with 1-chlorobutane, the product melted at 228—230° and showed characteristic absorption bands in the infrared spectrum at 1710 cm"1, 1620 cm-1, and 1550 cm"1. The product was N- (4,6 - dimethylpyrimidin - 2 - yl)aminocarbonyl benzenesulfonamide.

EXAMPLE 2 N - {(4 - methoxy - 6 - methylpyrimidin - 2 - yl)aminocarbonyl} - 2-chlorobenzenesulfonami de To a suspension of 280 g of 2-amino-4-methoxy-6-methylpyrimidine in 2000 ml of methylene chloride was added 434 g of 2-chlorobenzenesulfonyT 25 isocyanate with stirring. The resultant mixture was stirred for 16 hours - 16 - cooled to 10° and filtered to yield 470 g of a solid melting at 195—196°.

Mass spectrographic analysis showed this product to have a molecular weight of 356. ί 4983 Analysis-Calculated for C13Hl3ClN0,0lfS: C, 43.89%; H, 3.40%; N, 15.75% 5 Found: C, 43.37%; H, 3.56%; N, 15.30% This product was N - (4 - methoxy - 6 - methylpyrimidin - 2 - yl) - amino-carbonyl - 2 - chlorobenzenesulfonamide.

Partial evaporation of the filtrate caused precipitation of 20 g of by-product material melting at 160—162°. The infrared absorption spectrum 10 of the by-product was similar to the first precipitate, and it had a molecular weight of 356.

Analysis-Calculated for C13H13C1N01,01(S: C, 43.89%; H, 3.40%; N, 15.75%; Found: C, 44.09%; H, 3.56%; N, 14.97%.

By using an equivalent amount of an appropriate 2-ami nopyrimidine 15 and an appropriately substituted benzenesulfonyl isocyanate, the following compounds of Formula I can be prepared by the procedure of Examples 1 or 2: - 17 - ' TABLE I—A 44983 _h /H3 /—S°*NH^NH -i / r/ R3 ch3 > R3 Ri* R5 Rb R7 ro.p. Η Η Η Η H 228—230 F Η Η Η H 218—219 CH3 Η Η Η H 195—196 Cl H H Η H 204—205 Η Η H N0Z H 193—196 Η Η H CF3 H 183(d) H Cl Η Η H 142—143 —CF3 Η Η Η H 218-220 N0Z H H H H - Cl Η H —SOCH3 H -- Cl Η H —;S0C2H5 H - CH30— H CH30— Η H 198—199 Cl Η Η N02 H - CH3 Η H N0Z H 191—192 CH3 Η H —CH(CH3)2 H 157—160 CH3 Η H Cl H 209—211 - 18 - R3 Ri, B5 Rg R7 m.p.

TABLE I—A (Continued) 4*083 Cl Η H CH3 Η 2Π—213 F Η H F H 189—190 I Η H CH3 H - CH3S— H H N02 H - CH3O— Η H CH3 H 193—194 Cl Η Η H CH3 230—232 Cl Η Η H Cl 177—182 F Η Η H F 208—211 Cl Cl Cl Η H 215—217 Cl H Cl Cl H 204—205 —CH(CH3)2 H Cl —CH(CH3)2 H 131—136 _n—Ci|HgO Η Η n—C^HgO H n—C^Hg Η H —Ci|Hg H CN Η H CN H C2H5SOz— H H H H CH3S02— H H H H CH3 H CH3 H CH 227—231(d) F H F H F 173—180 Cl H Cl H Cl 208—210 CH30— H CH30— H CH3O— 192—193 Cl Cl H Cl Cl 220—222 CH3 CH3 h" CH3 CH3 244—246 Cl Cl Η Η H 195—197 - 19 - R3 Ri( R5 R6 R7 m.p.

TABLE I—A (Continued) 44983 Cl CH3 Η Η H 196—199 CH30— Cl Η Η H 179—180 F Cl Η Η H 196-197 CH3 Cl Η Η H 208—209 Br H Br H Bn - Cl H Cl Η H 202—205 F H Cl Η H 202—203 —S0CHa Η Η Η H - H Cl Cl Η H 210—212 Cl F Η Η H - H Cl H Cl H 199—202 F Η H CH3 H 210—212 CH3 Η H ' F H 200-201 Cl Η H CH30— H 198—199 Bn Η H Br H 211—212 CH30— Η H, CH30— H 193—195 CH3 Η H CH3 H 204—205 CH3 Η Η Bn H 205—207 C2H5O— Η H C2H5O—' H 208—210 CH30— Η H F H 199—201 Cl Η H Cl H 212—213 Η Bn Η I H - 20 - TABLE I—A (Continued) U°S3 R3 R4 Rs R6 R7 m.p. κ Η Η H CH3S— H Η Η H C2H5S02— H CH30— Η H Cl H 209—210 TABLE I—B \ /7 \-so2nhcnh - Rit R3 R3 Ri* R5 Rs R7 ra.p. Η Η Η Η H 204—205 H CH3 Η Η H 149—151 Br Η Η Η H 210—211 F Η Η Η H 198—199 CH3 Η Η Η H 172—174 CN Η Η Η H - —S03CH3 Η Η Η H 170—171 Η H Br N02 H - H Cl Η Η H 151—153 - 21 - 44983 TABLE I—β R3 Riv R5 βε R7 m.p. Η Η H CF3 H 150—152 Η H F CN H - Η Η H —S02CH3 H , Η Η H —S02C2H5 H - Cl Cl Η Η H 199—200 Cl CH3 Η Η H 177—186 CH3O Cl Η Η H 190—193 CH3 Cl Η Η H 190-192 F Cl Η Η H 193—195 Cl F Η Η H - CH3 Br Η Η B r - C2H5 H H H C2H5 - H Cl H Cl C2H50— - H Cl Cl Η H 193—195 —CitHgO— Η Η n—Ct^HgO— Η 182—1 S3 F H Cl Η H 206—208 I H Η Η H N02 Η Η Η H 223—225 CF3 Η Η Η H 194—197 Cl H F Η H 199—201 Cl H Cl Η H 195—197 Cl H ' CH30 Η H - - 22 - TABLE I—Β (Continued) ***θ3 R3 1¾ R5 R6 R7 m.p.

H Cl H Cl H 207—211 H CH3 CH3 Η H 193—196 C2H5S— H H N02 H - F Η H F H 177—178 CH30— Η H Cl H 199—200 CH3 Η H Cl H 206—207 C2Hs0— Η H C2Hs0— H 175—177 Cl Η H CH3 H 197—200 CH3 Η H N02 H 194—195 CH3 Η H —CH(CH3)2 H 136—142 Cl Η Η N02 H 178—180 CH3 Η H CH3 H 174—176 CH3 Η H Br H 195—197 Br Η H Br H 207—209 CH3Q— Η H CH30— H 175—177 Cl Η H Cl H 174—179 F Η H CH3 H 207—208 CH3 Η H F H 173—175 Cl Η H CH30— H 199—200 C2H5 Η H CjjHg H - CMH9 H H C2H5 H -- CH30— H H CH3 H 180—182 - 23 - R3 Rif R5 R6 R7 m.p.

***** TABLE I—8 {Continued} F Η Η H F 192—195 Cl Η Η H Cl 148—153 Cl Η Η H CH3 166—170 C2H5S02— H H H H - CH3S— Η Η Η H 200—202 C2H50— Η H Cl H 180—183 Cl Η H —SOCH3 H - Cl Η H —S0C2H5 H - Cl Cl Cl Η H 186—187 Cl H Cl Cl ' H 189—190 CH3 H CH3 H CH3 203—205 F H F H F 197—199 Cl H Cl H Cl 181—186 CH30— H CH30— H CH30 185—187 Cl Cl H Cl Cl 215—218 CH3 CH3 H CH3 CH3 223—226 CH30 Cl H Cl H 181—183 CH3 Cl Η N02 H 182—183 - 24 - 44983 TABLE I—C R6 r7 ,och3 \-/ 0 N r5—/ ^—so2nhcnh ——y J 0CH3 K Η Η Η Η H 202—203 F Η Η Η H 200—201 Cl Η Η Η H 179—181 CH3 Η Η Η H 184—186 S0zC2H5 H H H H - Η Η Η N02 H - H Cl Η Η H >250 Η Η H CF3 H 190—191 Cl Η H CH3S— H - Cl Η H C2H5S— H - CH30— Cl Η Η H 183—184 F Cl Η Η H 244—245 F H Cl Η H 223—224 Cl H F Η H 203—205 Cl H Cl Η H 190—191 —S0C2H5 H H N02 H - CH3O— H CH3O— Η H 182—184 - 25 - R3 Rif R5 Rg R7 m.p.

TABLE I—C CH30— Η H CH3 H 227—229 Cl Η H CF3 H 161—162 F Η H F H 210—212 Br Η H Br H 201—204 CH30— Η H CH30— H 198—199 CH3 Η H Br H 170—172 Cl Η Η N02 H 225—228 Cl Η H CH3O— H 180—181 C3H7O— Η H C3H70 H 188—189 n—Ctf HgO—— Η H j>—CifHgO— H 165—167 C2H50— Η H C2H50— H 181—183 CH30— Η H F H 192—194 CH30— Η H Cl H 197—198 Cl Η H Cl H 189—190 CH3 Η H Cl H 181—183 Cl Η H CH3 H 216-217 CH3 Η H H02 H 205—207 CH3 Η H —CH(CH3)2 H 110—116 CH3 Η H CH3 H 187—189 CH3O— Η Η I H - CH30— H CH30— Η H 173—175 Cl Η Η H CH3 171—174 - 26 - R3 Rij R5 Rg R7 ra.p.

TABLE I—C (Continued) 44983 CH3 H CH3 H CH3 197—198 F H F H F 219—221 Cl H Cl H Cl 194—195 CH30— H CH30— H CH30— 180—181 Cl Cl H Cl Cl 223—224 CH3 CH3 H CH3 CH3 182—184 CF3 Η Η Η H 219—220 CH30 Cl H Cl H 183—185 CH3 Cl Η N02 H 225—227 TABLE I—0 Re r7 ,CH3 V 'C 1? rb—(7 V-so2nchn -----(/ ) W 4 W R( J, X R3 Rif R5 Rg R7 X m.p, Η Η Η Η Η H 187—189 CH3 Η Η Η H —CH2OCH3 157—158 Cl Η Η Η H —CH20CH3 179—180 Cl Η H Cl H —CH20CH3 174—176 - 27 - R3 Rt, Rg Rg R7 X in.p· TABLE I—D (Continued) 44*9ί CH3O— Η H CH3O— H —CHjOCH3 155—157 F Η Η Η Η H 192—193 CH3 Η Η Η Η H 211—213 Cl Η Η Η Η H 201—203 H Cl Η Η Η Η 198—199 F Cl Η Η Η H 219—220 CH3 Cl . Η Η Η H 211—213 F H Cl Η Η H 222—235(d) H Cl H Cl Η H 201—203 CH30— Η H Cl Η H 224—226 Cl Η H Cl Η H 207—209 CH3 Η H Cl Η H 217—219 F Η H F Η H 173—199 Cl Η Η H Cl H 160—163 Η H . Η Η H C2H5O— 180—182 Cl Η H Cl H CzH50— - CH3 Η H Cl H C2H5O— - ch3 h h ch3 h c2h5o— - Η Η Η Η H (CH3)zCHO— 116—120 Η Η Η Η H Cl 213—215 CH3 H H H H Cl - H Cl Η Η , H Cl 194—195 Cl Η H Cl H Cl -- - 28 - 44983 R3 R^ R5 Rg R7 X ra.p.

TABLE I—D (Continued) CH3 Η H Cl H C2H5 - ch3 h h ch3 h ch3 - CH3 Η Η Η H Bn - Cl Η Η Η H Bn - Cl Η H Cl H Bn - Η Η Η Η H CH3S— 208(d) Cl Η Η H H CH3S— - CH3 H H H H CH3S— - Cl Η H Cl H CH3S— - CH3 H H CH3 H CH3S— - Η Η Η Η H —CF3 179—182 CH3 Η Η Η H —CF3 172—174 Cl Η Η Η H —CF3 173—175 Η Η H —CF3 H —CF3 160—163 Cl Η H Cl H —CF3 - CH3 ‘Η H Cl H —CF3 - CH3 H H CH3 H —CF3 - - 29 - TABLE I—E 44983 ^6. R7 ogh3 yi r Rs—// v)— so2nhcnh -f y r4 r3 R3 Rn R5 Rs R7 X m.p. Η Η Η Η Η H 199—200(d) Η Η Η Η H —CH2OCH3 - CH3 Η Η Η H —CH2OCH3 - Η Η Η Η H Cl 181—183 Cl Η Η Η H Cl 185—188 CH3 Η Η Η H Cl 176—178 Cl Η H Cl H Cl - CH3 H H CH3 H Cl - H Η Η Η H CH3S— 194—196 Cl Η Η Η H CH3S— -- CH3 H H H H CH3S— - Cl Η H Cl H CH3S— - CH3 Η H Cl H CH3S— - Η Η Η Η H —CF3 164—168 Cl Η Η Η H —CF3 204—208 - 30 - TABLE I—E (Continued) R3 Rtf R5 Rg R7 X ΐ"·Ρ· 44083 CH3 Η Η Η H —CF3 171—173 Η Η H —CF3 H —CF3 191—194 Cl Η H Cl H —CF3 - CH3 H H CH3 H —CF3 - Η Η Η Η H C2H50— 163—165 Cl Η Η Η H C2H50— 142—144 CH3 η η η H C2H50— 148—149 Cl Η H Cl H C2H50— - CH3 H H CH3 H C2H50— - EXAMPLE 3.

N-{(4,6-dimethylpyrimidin-2-yl)aminocarbonyl}-2-thiophenesulfonamide To 12 g of 2-amino-4,6-dimethylpyrimidine in 250 ml of acetonitrile 5 was added, with stirring, 19 g of 2-thiophenesulfonyl isocyanate. The resulting mixture was stirred for 2 hours and filtered to yield the desired solid product, m.p. 215—216°. The infrared spectrum for this product showed absorption peaks at 1540 cm'1, 1605 cm'1, and 1700 cm"1.

EXAMPLE 4.

N - {(4,6 - dimethylpyrimidin - 2 - yl)ami nocarbonyl} - 2,5 - dichloro-3 - thiophenesulfonamide To a suspension of 12 g of 2-amino-4,6-dimethyl-pyrimidine in 300 ml of methylene chloride was added at ambient temperature 26 g of 2,5-dichloro- - 31 - . 4&883 3-thiophenesulfonyl isocyanate. After stirring for 16 hours, the resulting solution was evaporated to dryness and the desired product, obtained as a solid residue, was triturated with ethyl ether and filtered. The solid product thus obtained melted at 192—194° and showed infrared absorp-5 tion peaks at 1550 cm'1, 1605 cm-1, and 1690 cm"1., EXAMPLE 5.

N-{(4-methoxy-6-methylpyrimidi n-2-yl)ami nocarbonyl}-2-furansul fonami de To a solution of 2.10 g of 2-furansulfonyl isocyanate in 40 ml of methylene chloride was added 1.60 g 2-amino-4-methoxy-6-methylpyrimidine.

The resulting mixture was stirred for 1 hour at room temperature, then refluxed for 15 minutes, and the solvent was removed under vacuum. The solid obtained was allowed to stand under ethyl ether containing a trace of acetonitrile for one day, and was then filtered and dried to give the desired product melting at 185—188° (dec).

By using an equivalent of an appropriate 2-amino-pyrimidine and an appropriately substituted thiophene or furansulfonyl isocyanate, the following compounds of Table II can be prepared by the procedures of Examples 3—5: - 32 - TABLE II—A. *49 83 / S02NhI-NH —^ ^—H Z Rq Q X Z m.p.

H S CH3 CH30— 207—208 H S CH30— CH30— 206—207 Cl S CH3 CH30— 186—187 Cl S CH3 CH3 198—199 Cl S H CH3 197—198 CH3 S ch3 CH30— H S Cl CH30— H S n—C3H70 CH30— H S Br CH30— H S CF3 CH30— H S CH3S— CH30— H S CH3OCH2— CH3 Cl S CH30“*— ch3o— Br S CH30— CH 3 0— ch3 δ ch3o— ch3o— Br S CH3 CH30— Cl s ch3 ch3 H 0 CH30— CH30— - 33 - ' ' TABLE II—A (Continued) 44S83 ., . .

Re Q X Z m.p, H 0 CH3 CH3 Br S CH3 CH3 CH3 S ch3 ch3 TABLE II—B ? ' . so2nhcnh —v y— h /X · R3 Rjq X Z m* p.

Cl Cl CH3 CH30— 186—188 Cl Cl 'CH30~ CH30— 201—202 CH3 ch3 CH3 ch3 ch3 ch3 ch3 ch3o— Bn Br . CH3 CH3 CH3 Cl CH3 ch3 Br Br CH3 CH3Q— CH3 CH3 CH30-— ch3o—" Η H CH3 CH30— - 34 - 44983 EXAMPLE 6.

N-{(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl}-l-naphthalene sulfonamide To a suspension of 15.6 g of 2-ami no-4,6-dimethoxy pyrimidine in 400 ml of acetonitrile was added 23.3 g of 1-naphthalenesulfonyl isocyanate 5 with stirring. After continued stirring for 14 hours, the desired solid product was removed by filtration, and after being washed with a small amount of ethyl ether, melted at 177—178°.

By using an equivalent amount of an appropriate 2-ami nopyrimidine and 1-naphtha!enesulfonyl isocyanate, the following Formula I compounds can be 10 prepared by the method of Example 6: N - {(4 - chloro - 6 - methylpyrimidin - 2 - y1)aminocarbonyl} - 1-naphthalenesulfonamide, m.p. 205—207°.

N - {(4,6 - dimethylpyrimidin - 2 - yl)aminocarbonyl} - 1 - naphthalene-sulfonamide, m.p. 201—202°, 15 N - {(4 - methylpyrimidin - 2 - yl)aminocarbonyl} - 1 - naphthalene- sulfonamide, m.p. 182—183°.

N - {(4 - methoxy - 6 - methylpyrimidin - 2 - yl)aminocarbonyT}- 1-naphtha!enesulfonamide, 210—211°.

EXAMPLE 7.

N-{(4,6-Dimethylpyrimidin-2-yl)aminothioxomethyl}benzenesulfonamide To a dry suspension of 12.4 g of 2-ami no-4,6-dimethyl pyrimidine in 60 ml of acetonitrile was added 19.9 g of benzenesulfonyl isothiocyanate.

The heavy white precipitate which formed was removed by filtration and washed with anhydrous ethyl ether. It melted at 165°—170°. The product 25 was N-{(4,6-dimethylpyrimidin-2-yl)-aminothioxomethyl}benzenesulfonamide.

By using an equivalent amount of the appropriate sulfonyl isothio cyanate and an appropriately substituted ami nopyrimidine, the compounds of Table III can be prepared by the procedure of Example 7: TABLE III—A Rev X Rs \ VsOzNHC-NH—? J Η K R* r3 z R3 Rt+ R5 R6 R7 X Z ifl.p. Η H f Η Η H CH3 CH3O— 188—189 Η Η Η Η H CH30 CH30 192—193 Cl Η Η Η H CH3 CH3 C2H5SO2 Η H CH3S02 H CH3 CH30 Cl Η Η Η H CH3 CH30— 184—185 Cl Η Η Η H CH30— CH30— 169—172 Cl Η H Cl H CH3 CH3 Cl Η H Cl H CH3 CH30— CH3 Η H F H CH3 CH3 CH3 Η Η Η H CH3 CH30 165—167 CH3 Η Η Η H CH30— CH30— 181—182 Cl Η Η H Cl CH3 CH30— CH30— Η H CH3— H CH3 CH3 - 36 - TABLE III—A (Continued) 44Θ83 R3 R4 R5 R6 R7 X Z m.p.

CH3O— Η H CH3O— H CH3 CH30— 178—180 CH30— Η H CH30— H CH30— CH30— 191—193 Cl Η H Cl H n—C3H7 CH30— Cl Η H N02 H CH3 CH30— Cl Η H CF3 H CH3O— CH3O— Cl Η Η N02 H CH3 CH3 CH30— Η H Cl H CH3 CH30— CH30— Η H Cl H CF3 CH3 Cl H Cl Η H CH3S— CH30— Cl H Cl Η H CH30CH2— C2HsO Η H C2HsO— H CH 3 0— CH3 CH3 H CH3 H CH30 CH3 CH30— ch3 h ch3 h ch3 ch2h5 ch3 ch3 h ch3 h ch3 ch3o— CH30— Η Η H CF3 H CH3 CH30— ch3 f h no2 h h ch3o— ch3 f h ,no2 h h ch3o— i>—-CijH9 Η H o-C^Ha H Cl CH3 ft-C4H30- Η Η η—€4Η90- H Br CH30— F Cl Cl H H CH30— CH30— CH3 Η H Cl F CH30— CH30— N02 Η Η H Br CH30— CH30— - 37 - 44983 I TABLE III—A (Continued) R3 Ri* R5 R$ R7 X Z m.p.

Cl Η H Cl H CH30— CH3O— I CH3 Η I H CH 30— CH30— CF 3 H F Η H CH3O— CH3O- CN H CH3OCN ' H CH30— CH30— CH3S— H H CH3S— H CH30— CH3O— TABLE III—B Re Ns/ \ V h X z H CH3 CHa H CH3 CH3O— 196-197 H CH3O— CH3O— 202-204 Cl CH3 ch3 Cl CH3 CH3O— Cl CH30— CH3O— ch3 ch3 ch3 ch3 . ch3 ch3o— ch3 ch3o— CH30— - 38 - TABLE III—B 449 8 3 Re ’ X Z Br CH3 CH3 Br CH3 CH30— Br CH30— CH30— TABLE III—C i N~\ — SQjiNHCNH -f V /3s Rg 'g/ *10 Rg Rlo X Z CH3 ch3 ch3 ch3 ch3 ch3 ch3 ch3o— ch3 ch3 ch3o— ch30— Cl CL CH3 CH3 Cl Cl ch3 ch3o— Cl Cl ch3&— ch3o— Η H CH3 CH30— Br Br CH3 CH30— - 39 - 4493® EXAMPLE 8. 2-Furansulfonylisocyanate Cl2 j A \ ΝΗι,ΟΗ -./Λ excess (C0C])2 r\ HaO.HCl \o/\ O'5 N/\)2NH2 \/S02NC0 A. Lithium-2-furansulfinate 5 To a solution of 39.6 g furan (585 mm) in 200 ml anhydrous ethyl ether was added carefully, under nitrogen atmosphere, 400 ml 1.6 Μη-butyl lithium in hexane while maintaining the reaction temperature at 30° or lower. The mixture was stirred until precipitation appeared complete. After cooling to -25 to -30°, excess gaseous sulfur dioxide was slowly passed through 10 the mixture during a 2-hour period. The mixture was stirred at room temperature for an additional 90 minutes and the precipitated lithium-2-furan-sulfinite was filtered and washed with acetone, m.p. 250°. IR (Nujol; registered Trade Mark for a'heavy mineral oil) 3400—3000 cm-1 (W), 1700 cm-1, 1550 cm"1 (VW), 1210 cm"1, 1140 cm"1, 1115 cm"1 (m), 1020 cm"' (VS), 910 15 cm" 880 cm"', 825 cm"1, (W), 735 cm"1 (S). - 40 - 44983 B. '2-Furansulfonyl chloride Ninety ml of water, 410 ml of cone. HC1, and 68.0 g of lithium 2-furansulfinate were stirred and cooled to 10—15°. Liquid chlorine (12.3 ml, 39.4 g) was added dropwise over a 30-minute period. The mixture 5 was stirred an additional 30 minutes at 5°, poured onto ice and extracted with methylene chloride.. Evaporation of the methylene chloride yielded 44 g 2-furansulfonyl chloride, Ip.p. 95° at 7 mm Hg; IR (neat) 3400 (m), 3120, 1800, 1550 (m), 1450 (S), 1380 (VS), 1210, 1160, 1120 (VS), 1035 (m), 1010 (VS), 913, 882 (S).

C. 2-Furansulfonamide Twenty-three g of 2-furansulfonyl chloride (138 mm) was added drop-wise into 200 ml of cone. ΝΗι,ΟΗ at 0—5°. After stirring overnight at room temperature, the water was removed under vacuum and the precipitate washed with ice water and dried. Yield: 14 g 2-furansulfonamide m.p. 120— 15 122°, (literature m.p. 120—122°: J0C 18, 894 (1953)). IR (Nujol) 3250 cm"1, 3100 cm"1, 1600 cm"1, (W), 1550 cm"1,1310 cm"1, 1190 cm-1, 1140 cm"1, 1120 cm"1, 1055 cm"1, 1005 cm"1, 930 cm"1,880 cm"1, 843 cm'^S), D. 2-Furansulfonyl isocyanate Dry toluene (150 ml). 25 ml oxalyl chloride (295 mmol), and a trace 20 of DABC0 (diaza-bicyclo{2.2.21octane) were heated to 90°. Ten g of 2- furansulfonamide was added over a 15 minute period and the mixture was held at 95° for 2 hours. After filtering, the solvent was removed under vacuum to yield 2.1 g of an oil showing the characteristic isocyanate absorption in the infrared (2280 cm"1). - 41 - 44983 ι EXAMPLE 9.

N-ί(4,6-Dimethyl-1,3,5-triazin-2-yl)aminocarbonyl}-2-methylbenzenesulfon-ami de To 12.3 g 2-ami no-4,6-diniethyl-l ,3,5-triazine in 250 ml of dry acetonitrile was added, with stirring, 19.7 g of 2-methylbenzene sulfonyl iso-5 cyanate at a rate designed to avoid excessive heating of the reaction mixture. Stirring was continued until the desired product crystallized.

The product was removed by filtration washed with a small amount of ethyl ether and dried. The resulting product, N-{(4,6-dimethyl - 1,3,5 - tria-zin - 2 - y 1) ami nocarbonyl} -2-methyl benzenesul fonami de, melted at HI— 10 145°C.

EXAMPLE 10.

N-{(4,6-Dimethyl-1,3,5-triazin-2-yl)amino carbonyl}-2-chlorobenzenesulfon-amide To 12.3 g of 2-amino-4,6-dimethyl-l,3f5-triazine in 200 ml of aceto-15 nitrile was added with stirring 21.7 g of 2-chlorobenzenesulfonyl isocyanate. All of the solid dissolved after the reagents were added and the mixture was then evaporated to dryness. The solid residue was triturated with ethyl ether and isolated by filtration to give impure N-{4,6-dimethyl- 1,3,5-triazin-2-yl)ami nocarbonyl-2-chlorobenzenesulfonamide melting at 20 115—118°C. The nuclear magnetic resonance absorption spectrum of this product, in trifluoroacetic acid, showed singlet peaks at 2.69 and 2.9 parts per million.

EXAMPLE 11.

N-{(4,6-dimethoxy-l,3,5-triazin-2-yl)aminocarbonyl}-2-chlorobenzenesulfon-25 amide - 42 - 44β83 i To 15.6 g of 2-amino-4,6-dimethoxy-l,3,5-triazine in 300 ml. of dry methylene chloride containing 0.1 g l,4-diazabicyclo{2,2,2}octane was added 21 g 2-chlorobenzenesulfonyl isocyanate with stirring. The mixture was stirred for 16 hours and the resultant solid was removed by filtration.

After washing the solid with 1-chlorobutane, the resulting product N-{4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl}~2-chlorobenzenesulfonamide melted at 188—189°C. Infrared absorption analysis showed absorption peaks at 1740 cm-1, 1630 cm-1, and 1595 cm-1 which are typical for this type of compound.

By using the procedure of Examples 9—11 with an equivalent amount of the appropriate aminotriazine and the appropriately substituted sulfonyl isocyanate, the compounds given in Table IV can be prepared: TABLE IV—A X, f~\ S /~\ \-S0zNHCNH -4 N \=/ N X 2 m.p.

CHj— CH3— 200—201 CH30 CH30 183—185 CH30 CH3 166—171 Cl CH30 - 43 - TABLE IV—A (Continued) 449®·*' X Z m.p.

C2H5 CH30 CH3OCH2 CH30 CH3CH2CH2Q CH30 121— 124 (CH3)2CH0 CH30 CH3S CH30 197—199 (CH3)2CH0 ch3 ch3s ch3 ch3ch2o ch3 H CH30 CF3 CH30 Br CH30 - 44 - TABLE IV—Β 4*083 /~\ t // \V-S02NH-C-NH —(/ Ν ' R3 ~~^Ζ R3 X Ζ m.p.°C CH3 CH30 CH3 158—162 CH3 CH30 CH30 144—147 CH3 CH3OCH2 CH3 147—150 CH3 (CH3)2CH0 CH30 ch3 ch3ch2ch2o ch3o CH3 CH3S CH30 191—193 Cl CH3 CH3 185—187 Cl CH30 CH3 174—178 Cl CH30 CH30 188—189 Cl CH30CH2 CH3 142—145 Cl CH3CH20 CH3 117—121 Cl CH3CH20 CH30 132—133 I CH3 CH3 F CH30 CH3 168—172 F CH30 CH30 169—175 CF3 CH3 CH3 172—174 - 45'· I *· TABLE IV—B (Continued) R3 X Z m.p.°C -,-1-J- CF3 CH3 CH30 165—167 N02 CH3 CH3O 178—181 dec.

N02 CH30 CH30 175—178 CH3 ch3s ch3 ch3 H ch3 ch3 ch3ch2o ch3 CH3 (CH3)zCH0 ch3 Cl H CH3 _ .

Cl ch3s ch3 Cl Cl ch3 Br CH3 CH3 Br CH3 CH30 Br CH30 CH30 N02 CH3 CH3 105—110 F H CH3 F CH3S CH3 F CH3CH20 CH3 F (CH3)2CH0 CH3 CH3S CH30 CH3 181—184 F CH3CHiO CH30 CH30 CH3 CHa - 46 - 44t>83 TABLE IV—B (Continued) R3 X Z m.p.°C C2H5S02 H ch3 CH30 . CH3S ch3 CH30 CH3CH20 CHg n-CijHgO Cl CH3 CH30 CH30 CH3 CH30 CH30 c2h5 ch3 ch3 c2hs ch3o ch3 c2h5 ch3o CH30 n-C^Hg CH3 CH3 (CH3)2CH ch3 ch3o (CH3)2CH ch3o ch3o n-C3H7 CH3O . CH30 CN CH30 CH30 - 47 - / V _ * TABLE IV—C ^ 49 8 3 jr\ i i'l // XV-SOoNHCNH Λ , w m z R6 X Z m.p.

Cl CH3 CH3 190—191 Cl CH3 CH30 Cl CH30 CH30 above 250 CF3 CH3 CH3 158—162 CH3 CH3 CH3 184 (resolidifies) CH3 CH3 CH30 CH3 CH30 CH30 174 (resolidifies) CH3 H ch3 ch3 ch3ch2o ch3 ch3 ch3ch2o ch3o Cl ch3s . ch3o Br CH3 CH3 Br CH30 CH3 Br ht30 CH30 no2 ch3 ch3 no2 ch3o ch3 no2 ch3o ch3o j - 48 - i * f jj - i 44983 TABLE IV—C (Continued) Rg X Z m.p.

CF3 ch3o CH30 cf3 ch3o ch3 ch3so2 ch3q CH30 ch3ch2so ch3o ch3o I ch3 ch3 F CH30 CH3 F C2Hs0 CH3 f c2h5o ch3o F CH3S CH30 F (CH3)2CH0 CH30 Cl H CH3 Br H CH30 CH30 CH3 CH3 * ch3o ch3o ch3 ch3o ch3o CH30 ch3o c2h5o ch3 ; ch3o c2h5o ch3o CH30 (CH3)2CH0 ch3o n-Ci*H90 H CH30 ch3o h ch3 ch3 ch3 ch3 c2hs ch3o ch3 - 49 - / TABLE IV—C (Continued) Rg X Z m.p. 44983 CN H CH3 ch3s ch3o ch3o c2h5 ch3s CH30 jT_~Ct|.Hg CH3 CH3 (CH3)2CH ch3 ch3o (CH3)2CH ch3o^ ch3o jt~C3H2 CH3 CH3 TABLE IV—D p ( )-S02NHCNH -f N K Ni 1¾ K3 L R3 Ri, X Z m.p.

Cl Cl CH3 CH3 130—140 Cl 1 Cl CH3 CH30 182—184 Cl Cl CH30 CH30 192—193 F Cl CH3 CH3 171—175 F Cl CH3 CH30 190—191 . j 4 - 50 - 'V* R3 Rt, X Z m.p.

TABLE IV—0 (Continued) 449Sa F Cl CH30 CH30 275 Cl CH3 CH 3 CH 3 188—189 Cl CH3 CH3 CH30 187 Cl CH3 CH3O CH3O 148—151 CH3O Cl * CH30 CH30 178 CH30 Cl CH 3 CH30 CH30 Cl CH3 ch3 CH3O Cl CH3S CH30 ch3 Cl ch3 ch3 ch3 Cl CH30 ch3 ch3 Cl CH30 CH30 ch3 f ch3 ch3 ch3 f < CH3 CH30 ch3 f · CH30 CH30 F CH3 - CH3 CH3 F CH3 CH3 CH30 F CH3 CH30 CH30 F F CH3S CH30 ch3 ch3 ch3 ch3o ch3 ch3 ch3 ch3 F Cl CH30 CH3 F H CH30 CH30 - 51 - TABLE IV—D (Continued) R3 Rt, X Z m.p. 44983 F F CH30 CH30 F F CH30 CH3 F - F CH3 CH3 ch3 CH3 CH30 CH30 CH30 CH3 ch3 ch3 CH30 F CH3 CH3 CH30 F CH30 CH30 CH3 ΒΓ CH30 CH30 Cl Br CH30 CH30 C2H5 Cl CH3 CH30 TABLE IV—E R 5-(())- SO2NHCNH-(( N r3 nz R3 R5 X Z m.p.

Cl Cl CH30 CH30 182—190 Cl Cl CH3 CH30 Cl Cl ch3 ch3 - 52 - TABLE IV—e (Continued) *4083 ....... .1.1» ......! .1. 1,^.1.'«............—1—" .................""" R3 R5 X Z m.p.

F F CH30 CH30 F F CH3 CH30 Cl F CH3 CH30 Cl F CH3 CH30 CH3 F ch3 CH30 ch3 f ch3o ch3o F Cl CH30 CH30 F Bn CH3 CH30 ch3 ch3o ch3 ch3o ch3 ch3 ch3o ch3o ch3 Cl ch3o ch3o ch3o Cl · ch3 ch3o cf3 f ch3 ch3o cf3 f ch3o ch3o - 53 - TABLE IV—F 44983 \ v \-, 0 N—( (( JV-so2nhcnh-P N r3 z R3 R6 X Z m.p.

Cl Cl CH3 CH3 190—192 Cl Cl CH3 CH30 186—188 Cl Cl CH30 CH30 185—188 Cl Cl CH3CH20 CH3 155—159 Cl Cl CH3CH20 CH30 147—149 CH3 ch3 ch3 ch3 CH3 CH3 CH3 CH30 160—163 CH3 CH3 CH30 CH30 169—173 CH30 Cl CH3 ch3 CH30 Cl CH3 CH30 174—179 CH30 Cl CH30 CH30 165 CH30 Cl CH3CH20 CH3 183—183,5 CH30 F CH30 CH30 201—203 F Cl CH30 CH30 F Cl CH3 CH30 F F CH3 CH3 164—165 - 54 - TABLE IV—F (Continued) 44Sg3 R3 Rg X Z m.p.

F F CH3 CH30 F F CH30 CH30 206—208 Cl F CH30 CH30 Cl F CH3 CH3 Cl CH30 CH3 CH30 176 Cl CH30 CH30 CH30 201 Cl CH30 CH3 ch3 Cl CF3 CH3 CH30 177—178 Cl CF3 CH3O CH 3O 165—167 Cl N02 CH3 CH3 142—144 Cl N02 ' CH3 CH30 Cl N02 CH30 CH30 168—174 CH3 CH30 CH3 ch3 ch3 ch3o ch3o CH30 CH30 CH3 CH30 CH3 CH30 CH3 CH30 CH30 210—213 CH30 ch3 ch3 ch3 Cl ch3 · ch3 ch3 Cl ch3 ch3 ch3o Cl ch3 . CH30 CH30 F CH3 CH3 CH3 180—182 F CH3 CH3 CH30 185—186 - 55 - 44983 TABLE IV- F (Continued) ' ' ‘ " · — f \· " ' * '............

R3 R6 X Z ra.p.

F CH3 CH30 CH30 191—192 CH3 F CH3 CH3 201—205 CH3 F ch3 ch3o CH3 F CH30 CH30 183—184 F CH3 (CH3)zCH0 ch3o F CH30 CH3 CH3 F CH30 CH3 CH30 F CH30 CH30 CH30 ch3 cf3 ch3 ch3 ch3 cf3 ch3o ch3o ch3 (ch3)2ch ch3o ch3o F CF3 CH3 CH30 F CF3 CH30 CH30 CH3 Br CH30 CH3 Cl Br CH3 CH3 ch3 ch3so2 ch3o ch3o ch3o no2 ch3s ch3o Br F Cl CH3 CH30 (CH3))>CH ' Br CH30 (CH3)2CH CH30 1 CH3S CH30 F CH3 H CH3 CH3 N02 CH3 CH30 190—191 - 56 - R3 Rg X Z m.p.

TABLE IV-—F' (Continued) 'ί40β3 CH3 N02 CH30 CH30 1 42—145 CH3 no2 ch3 ch3 CH3 (CH3)2CH CH3 CH3 167 CHj (CH3)2CH CH3 CH30 115 CH3 (CH3)zCH CH30 CH30 135 CH3CH2O Cl CH3 CH30 179—181 CH3CH2O CH3CH20 CH3 CH3 134—136 CH3CH20 CH3CH2O CH30 CH3O 187—188 CH3 Cl CH3 CH3 183—191 CH3 Cl CH3 ch3o ch3 Cl ch3o ch3o Cl ch3 ch3 ch3 Cl ch3 ch3 ch3o Cl ch3 ch3o CH30 Br B r CH3 CH3 204—205 Br Br CH3 CH30 178—180 Br Br CH30 CH30 above 275 CH30 CH30 CH3 CH3 144—150 CH30 CH30 CH3 CHs0 187—205 (dec) CH30 CH30 CH30 CH30 187—188 CH30 CH30 CH3CH20 CH3 96—100 CH30 CH30 CH3CH20 CH30 138—141 - 57 - TABLE IV—G 4 4983 Λ" j r3 \ R3 R7 X Z ra.p.

Cl Cl CH3 CH3 142—158 Cl Cl CH3 CH30 203—206 Cl Cl CH30 CH30 205—208 Cl B r CH30CH;. CH3 Cl C2H5 ch3 ch3 Cl CH3 CH3 CH30 171—172 Cl CH3 CH30 CH30 173—176 F F CH3 CH3 192—193 F F CH3 CH30 213—215 F F CH30 CH30 275 Cl CH30 CH30 ch3o C1 C2H50 CH30 CH30 - 58 - TABLE IV—Η 4 49 8 3 Rit Rg X Z m.p.

Cl Cl CH3 CH3 210—213 Cl Cl CH30 CH30 207 ch3 ch3 ch3o ch3 ch3 ch3 ch3o ch3o ch3 ch3 ch3 ch3 ch3 Cl ch3 ch3 ch3 Cl ch3o ch3 ch3 Cl ch3o ch3o ch3 f ch3o ch3o ch3 f ch3 ch3o ch3 f ch3 ch3 - 59 - TABLE IV-1 44993 R4 Rij R5 X Z m.p.

Cl Cl CH3 CH3 194—195 Cl Cl CH3 CH3O 188—190 Cl Cl CH30 CH30 280 TABLE IV—J ϊ R5 \( ) ) SOoNHCNH-(v N >r m Rif R3 z R3 Rif R5 X Z m.p.

Cl Cl Cl CH3 CH3 178—184 Cl Cl Cl CH3 CH30 169—171 Cl Cl Cl CH30 CH30 175—178 - 60 - TABLE IV—K 44*Sa R, X K »M /( ) V-SOzNHCNH-y " Μ M Κμ R3 Z r3 r4 r6 x z Cl Cl Cl ch3 ch3 Cl Cl Cl ch3 ch3o Cl Cl Cl CH30 CH3O Cl CHs Cl ch3o ch3 CH3 Cl CHs CH3O CH3 ch3o Cl ch3 ch3o ch3 TABLE IV—L ^/χ i /“< -S02NHCNH-^ .N R, R3 1 R3 Rfj R7· X Z m.p. ch3 ch3 ch3 ch3o ch3 Cl Cl Cl· CH30 CH30 F F F CH30 CH30 - 61 - R3 R 4 4 9 8 3 TABLE IV— L (Continued) CH3 Cl Cl CH30 CH3 176—178 CH3 Cl CH3 ch3o ch3 ch3 f ch3 ch3o ch3 TABLE IV—M R3 R*, Rg X Z m.p.

Cl Cl Cl CH3 CH3 184—186 Cl Cl G1 CH3 CH30 169—171 Cl Cl = CT · CH30 CH30 165—168 Cl CH3 ' Cl CH30 ch3 Cl ch3 no2 ch3o ch3 F CH3 Cl CH30 CH3 - 62 - TABLE IV—N a Rs \LJ/ SOzNHCNH J R3 R5 R7 X Z m.p.

CH3 CH3 CH3 CH3 CH3 205—207 CH3 CH3 CH3 CH3 CH30 177—186 CH3 CH3 CH3 CH30 CH30 160—167 F F F CH3 CH3 163—169 F F F CH3 CHjO 152—155 F F F CH30 CH30 194—196 Cl Cl Cl CH3 CH3 188—190 Cl Cl Cl CH3 CH30 159—161 Cl Cl Cl CH30 CH30 166—168 Cl Cl CH3 ch3 ch3o F F CH3 CH30 CH30 Cl ch3 ch3 ch3 ch3o ch3 f ch3 ch3 ch3o F Cl Cl ch3o ch3o F F Cl CH30 CH30 - 63 - TABLE IV—Ο 44983 RSv R7 X W o y—-V x n—/ /\ \ Ri+ R3 R3 Ri, Rs R7 X Z m.p.

CH3 CH3 CH3 CH3 CH3 CH3 ZOO—205 CH3 CH3 CH3 CH3 CH3 CH30 195—197 CH3 CH3 CH3 CH3 CH30 CH30 185—189 Cl Cl Cl Cl CH3 ch3 Cl Cl Cl Cl CH3 CH30 187 Cl Cl Cl Cl CH30 CH30 above 250 EXAMPLE 12 N-{(4-methoxy-6-raethyl-l,3,5-tn'azin-2-yl)-aminocarbonyl}-2-thiophenesul-fonaraide 5 To a suspension of 14.0 g of 2-amino-4-methoxy-6-n\ethyl- 1,3,5-triazine in 300 ml. of acetonitrile was added, dropwise, 19 g of thiophene-2-sulfoiiyl isocyanate. After stirring for six hours, the mixture was filtered to yield the desired solid product melting at 182—184°C.

By using the procedure of Example 12 with equivalent amounts of the 10 appropriate amino-1,3,5-triazine derivative and sulfonyl isocyanate the compounds of Table V c?n be prepared, - 64 - TABLE V—A ί(|θ83 Ο N ^ ,._— S02NHCNH -/ N Π W /s\.

Rg Rio X z ™·Ρ· Cl Cl CH3 CH3 127—133 Cl Cl CH3 CH30 165—171 Cl Cl CH30 CH30 181—184 CH3 ch3 ch3 ch3o ch3 ch3 ch3o ch3o Br Br CH30 CH30 Η H CH3 CH30 TABLE V—B Rsa N —( \ Re X Z Q m.p.

H CH3 CH3 S 174—176 - 65 - R8 X Z Q m.p.

TABLE V—B (Continued) 44083 H GH3 CH30 S 182—184 H CH30 CH30 S 191—192 CH3 ch3 CH30 S ch3 ch3o CH30 S ch3 ch3ch2o ch3o s Cl CH3 CH3 . S 192—195 Br CH3 CH30 S Cl CH30 CH30 S 193—195 H CH3 CH30 0 H CH30 CH30 0 EXAMPLE 13 N-{(4,6-Dimethoxy-l ,3,5-triazin-2-yl)aminocarbonyl}-l-naphthalenesulfonamide To a suspension of 16 g of 2-amino-4,6-dimethoxy-l ,3,5-triazine in 5 400 ml of acetonitrile was added 23.3 g of 1-naphthalenesulfonyl isocyanate dropwise with stirring. The mixture was stirred for 14 hours and the resultant solid product removed by filtration. After washing with ethyl ether the product melted at 171—172°C.

By using the procedure of Example 13 and substituting equivalent 10 amounts of the appropriate amino-1,3,5-triazine and sulfortyl isocyanatb, the following compounds of Table VI can be prepared. - 66 - 1 TABLE VI *4983 « /11 , SO,NHCNH “Λ " i N =/ X Z m.p.

CH3 CH3 179—183 CH3 CH30 186—188 CH30 Ch30 171—172 CH3OCH2 CH3 EXAMPLE 14.

N“{(4,6-Dimethoxy-l,3,5-triazin-2-yl)aminothioxomethyl}-benzenesulfonamide A mixture'containing 20 g of benzenesulfonyl isothiocyanate, 15.6 g 5 of 2-ami no-4,6-dimethoxy-l,3,5-triazine, 250 ml of acetonitrile and a catalytic amount of dibutyltin dilaurate was stirred for 24 hours. After filtration to remove unreacted triazine, the evaporation of the acetonitrile yielded a gummy residue. Trituration of this material with ethyl ether resulted in the precipitation of the desired compound, which was isolated 10 by filtration and melted at 148—150°C.

By using the procedure of Example 6 with an equivalent amount of the appropriate sulfonyl isothiocyanate and aminotriazine, the compounds of Table VII can be prepared. - 67 - 44083 TABLE VII S II RiS02NHCNHR2 Ri r2 ch3 O nch3 a^.0CH3 '“C, a- o -Q F T)CH3 - 68 - t TABLE VII (Continued) Ri R2 m*p. 1-λ . ^OCH, Q- Br och3 ( V _/ N 182—185 C' och3 ry jX w; A»-( och3 ry _/~f V-i==y 'n c' Vh, /-v )— —/ N 142—144 ch3 C3 - 69 - 448»3 TABLE VII (Continued) Ri R2 m.p.

C> /CH3 V /"X / \ N ( 'n—/ °CH3 I)CH3 ' ' N Nm c2h5 ™ ^och3 h3c fy. γΤ3 n-=/ ch3 N)ch3 CK )-s N —^"OCHg ( V j x och3 och3 CH3°x J)CH3 // \ /N—\ ( —/ N 188—190(d) XN==/ OCH, \ 3 0CH3 - 70 - 44983 Ri 1¾ m.p.

TABLE VII (Continued) OCl .OCH, T N=/ Cl CH3 Ck_v ^CH3 ry s*.

'-\ N==V ci toch3 h3C\__ jh3 Γν \ "“in, CH3\ Xti ry y-c \-=/ 'N—/ 0CH3 cl\__ W3 λ“\_ 71 \-Γ w 0CH3 0CH3 - 71 - TABLE VII (Continued) Ri R2 m.p. 44983 ,k n-/CH3 Os <1 och3 /OCHo CX -Q och3 Formulations Useful formulations of the compounds of Formula I can be prepared in conventional ways. They include dusts, granules, pellets, solutions, 5 suspensions, emulsions, wettable powders and emulsifiable concentrates.

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, 10 broadly, contain e.g.'0.11 to 99¾ by weight of active ingredient(s) and at least one of a) 0.1¾ to 20¾ surfactant(s) and b) 1¾ to 99.9¾ solid or liquid diluent(s). More specifically, they will contain these ingredients in the following approximate proportions: - 72 - *4 983 TABLE VIII Active Ingredient Diluent(s) Surfactant(s) Wettable Powders 20—90 0—74 1—10 Oil Suspensions, Emulsions, Solutions (including Emulsifiable Concentrates) 3—50 40—95 0—15 Aqueous Suspensions 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 Strength Compositions 90—99 0—10 0—2 Lower or higher levels of active ingredient can, of course, be present depending on the intended use and the physical properties of the compound. Higher ratios of surfactant to active ingredient are sometimes desirable, 5 and are achieved by incorporation into the formulation or by tank mixing.

Typical solid diluents are described in Watkins, et al., "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books, Caldwell, New Jersey. The more absorptive diluents are preferred for wettable powders and the denser ones for dusts. Typical liquid diluents and sol-10 vents are described in Marsden, "Solvents Guide", 2nd Ed., Interscience, New York, 1950. Solubility under 0.1¾ is preferred for suspension concentrates; solution concentrates are preferably stable against phase separation at 0°C. "McCuteheon1 Detergents and Emulsifiers Annual". MC Publishing Corp., Ridgewood, New Jersey, as well as Sisely and Wood, "Encyclopedia 15 of Surface Active Agents", Chemical Publishing Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor - 73 - 449®3 amounts of additives to reduce foam, caking corrosion or microbiological growth.

The methods of making such compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions 5 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. Browning, “Agglomeration", Chemical Engineering, Dec. 4, 1967, pp. 147ff. and “Perry's Chemical Engineer's Handbook" 4th Ed., McGraw-Hill, New York, 1963, pp. 8—59 ff.

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 Examples 10 through 41.

R. W, Luckenbaugh, U.S. Patent 3,309,192, March 14, 1967, Col. 5, line 43 through Col. 7, line 52 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138—140, 162—164, 166, 167, 169—182.

Hy 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.

J. D. Fryer and S. A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101—103.

In the following examples, all parts are by weight unless otherwise 25 indicated. - 74 - EXAMPLE 15 4 4383 Wettable Powder N-{(4,6-dimethylpyrimi di n-2-yl)ami nocarbonylJbenzene-sulfonamide 80¾ 5 sodium alkyl naphtha!enesulfonate 2% sodium li^ninsulfonate 2% synthetic amorphous silica 3¾ kaolinite 13¾ The ingredients are blended, hammer-milled until all the solids are 10 essentially under 50 microns and then reblended.

EXAMPLE 16 Wettable Powder N~{(4-methoxy-6-methy1pyrimidin-2-yl)-aminocarbonyl}- 2-chloro-5-methoxy benzenesulfonamide 50¾ 15 sodium alkylnaphthalenesulfonate 2% low viscosity methyl cellulose 2¾ diatomaceous earth 46¾ The ingredients are blended, coarsely hammer-milled and then air- solids milled to produce particles of active/essentially all below 10 microns in 20 diameter. The product is reblended before packaging.

EXAMPLE 17 Granule wettable powder of Example 16 5¾ attapulgite granules 95% 25 (U.S.S. 20—40 mesh; 0.84—0.42 mm) - 75 - 44983 A slurry of wettable powder containing λ25¾ solids is sprayed on the surface of attapulgite granules in a double-cone blender. The granules are dried and packaged.

EXAMPLE 18 5 Extruded Pellet N - {4 - methoxy - 6 - methyl pyritni din - 2 - yl) - ami nocarbonyl }- 2-chloro-benzenesulfonamide 25¾ anhydrous sodium sulfate 10¾ crude calcium ligninsulfonate 5¾ 10 sodium alkyl naphtha!enesulfonate 1% calcium/magnesium bentonite 59¾ The ingredients are blended, hammer-milled and then moistened with about 12¾ 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 15 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 (0.42tna operingsTnay be packaged for use and the fines recycled.

} EXAMPLE 19 Oil Suspension 20 N-{(4,6-dimeth0xypyrimidin-2-yl)-aminocarbonyl}-2,5-dichioro- benzenesulfotfariidb 25¾ polyoxyethyl4n^ sbrbitol hexaoleate 5¾ highly aliphatic hydrocarbon oil 70¾ The ingredients ^re ground together in a sand mill until the solid 25 particles have been.reduced to under about 5 microns. The resulting sus- - 76 - 4 9 s 3 pension may be applied directly, but preferably after being extended with oils or emulsified in water.

EXAMPLE 20.

Wettable Powder 5 N-{(4,6-dimethylpyrimidin-2-yl)-aminocarbonyl}-2,6- dichlorobenzenesulfonamide 20¾ sodium alkyl naphtha!enesulfonate 4¾ sodium ligninsulfonate 4¾ low viscosity methyl cellulose 3¾ 10 attapulgite 69¾ The ingredients are thoroughly blended. After grinding in a hammer mill to produce particles essentially all below 100 microns, the material is reblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) and packaged.

EXAMPLE 21 Low Strength Granule N-{(4-methoxy-6-methylpyrimidi n-2-yl)-ami nocarbonyl}-2- methylbenzenesulfonamide 1¾ Ν,Ν-dimethylformamide 9¾ 20 attapulgite granules 90¾ (U.S.S. 20-40 mesh).

The active ingredient is dissolved in the solvent and the solution is sprayed upon dedusted granules in a double cone blender. After spraying of the solution has been completed, the blender is allowed to run for a 25 short period and then the granules are packaged. - 77 - 44983 EXAMPLE 22 Aqueous Suspension N-i(4 ,6-dimethylpyrimi di n-2-yl) ami nocarbonyl1-benzene-sulfonamide 40¾ 5 polyacrylic acid'thickener 0.3¾ dodecylphenol polyethylene glycol ether 0.5¾ disodium phosphate 1¾ monosodium phosphate 0.5¾ Polyvinyl alcohol 1.0¾ 10 Water 56.7¾ The ingredients are blended and ground together in a sand mill to product particles essentially all under 5 microns in size.

EXAMPLE 23 Sol uti on 15 Μ(4-methoxy-6-methylpyrimidin-2-yl)-aminocarbonyl 1-2- chlorobenzenesulfortamide, sodium salt 5¾ water 95¾ The salt is added directly to the water with stirring to produce the solution, which may then be packaged for use.

EXAMPLE 24 Low Strength Granule N-{(4,6-dimethylpyrimidin-2-y1)aminocarbonyl}-2,6-di-chlorobenzenesulfonamide ~ 0,1¾ attapulgite granules 99.9¾ 25 (U.S.S. 20—40 mesh) - 78 - ^4983 The active ingredient h disco!ved 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 evaporate the solvent. The material is allowed to cool and then packaged.

EXAMPLE 25 Granule N-{(4,6-dimethoxypyrimidin-2-yl)-aminocarbonyl}-2,5-dichloro-benzenesulfonamide 80¾ wetting agent , 1¾ 10 crude ligninsulfonate salt (containing 5—20% of the natural sugars) 10% 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 15 flow is adjusted to gently fluidize the material, and a fine spray of water is sprayed into the fluidized material. The fluidization and spraying are continued until granules of the desired size range are made. The spraying is stopped,, but fluidization is continued, optionally with heat, until the water content is reduced to the desired level, generally less 20 than 1%. The material is then discharged, screened to the desired size range, generally 14—100 mesh (1410—149 microns), and packaged for use. - 79 - EXAMPLE 26 449®3 High Strength Concentrate N~{(4,6-dimethylpyrimidin-2-yl) aminocarbonyl 1-2-thiophene-sulfonamide 99¾ 5 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 27 Hettable Powder: N-{(4-methoxy-6-methylpyrimidin-2-yl)-aminocarbonyl1-2-chloro-benzenesulfonamide 95% dioctyl sodium sulfosuccinate 0.1% 15 synthetic fine silica 4.9% 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 28 20 Wettable Powder N-{(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl}-2,5-dichioro-benzenesulfonamide 40% sodium ligninsulfonate 20% montmorillonite clay 40% - 80 - 44983 The ingredients are thoroughly blended, coarsely hammer-mined and then air-milled to produce particles essentially all below 10 microns in size. The material is reblended and then packaged.

EXAMPLE 29 5 Oil Suspension N-{(4-methoxy-6-methylpyrimidin-2-yl)-aminocarbonyl}-2- methylbenzenesulfonamide 35% blend of polyalcohol carboxylic esters and oil soluble petroleum sulfonates 6% 10 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.

EXAMPLE 30 15 Wettable Powder N- ((4,6-dimethoxy-l3,5-tri azi n-2-yl) ami nocarbonyl) benzene- sulfonamide 80% sodium alkyl naphtha!enesulfonate 2% sodium ligninsulfonate 2% 20 synthetic amorphous silica 3% kaolinite 13% The ingredients are blended, hammer-milled until all the solids are essentially under 50 microns, reblended, and packaged. - 81 - 449®3 - EXAMPLE 31 Wettable Powder N-{(4,6-dimethyl-1,3,5-triazin-2-yl)-ami nocarbonylJbenzene- sulfonamide 50¾ 5 sodium alkylnaphthalenesulfonate 2% low viscosity inethyl cellulose 2¾ diatomaceous earth 46¾ The ingredients are blended, coarsely hammer-milled and then air- milled to produce particles essentially all below 10 microns in diameter, 10 The product is reblended before packaging.

EXAMPLE 32 Granule wettabl6 powder of Example 31 5¾ attapulgite granules 15 (U.S.S, 20—40 mesh; 0.84—0.42 mm) 95¾ A slurry of wettabfe powder containing «r25¾ solids is sprayed on the surface of attapulgite granules in a double-cone blender. The granules are dried and packaged.

EXAMPLE 33.

Extruded Pellet N-{(4-methoxy-6-methyl-1,3,5-triazi n-2-yl)-ami nocarbonyl}- 2-chlorobenzenesulfonamide 25¾ anhydrous sodium sulfate 10¾ crude calcium ligninsulfonate 5¾ 25 sodium alkylnaphthalenesulfonate 1¾ calcium/magnesium bentonite 59¾ - 82 - *498 3 The ingredients are blended, hammer-mined and then moistened with about 12¾ 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 5 a U.S.S. No. 20 sieve (0.84 mm openings). The granules held on a U.S.S. No. 40 sieve (0.42 mm openings) may be packaged for use and the fines recycled.

EXAMPLE 34 Oil Suspension 10 N-{(4,6-dimethoxy-l,3,5-triazin-2-yl)-aminocarbonyl}-2-chloro- 5-methoxybenzenesulfonamide 25% polyoxyethylene sorbitol hexaoleate 5% highly aliphatic hydrocarbon oil 70% The ingredients are ground together in a sand mill until the solid 15 particles have been reduced to under about 5 microns. The resulting suspension may be applied directly, but preferably after being extended with oils or emulsified in water.

EXAMPLE 35 Wettable Powder 20 N-{(4,6-dimethoxy-l,3,5-triazin-2-yl)-aminocarbonyl )-2- chlcrobenzenesulfonamide 20% sodium alkylnaphthalenesulfonate 4% sodium ligninsulfonate 4% low viscosity methyl cellulose 3% 25 attapulgite 69% - 83 - 44983 The ingredients are thoroughly blended. After grinding in a hammer mill to produce particles essentially all below 100 microns, the material is reblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) and packaged.

EXAMPLE 36 Oil Suspension N-{(4,6-dimethoxy-l,3,5-triazin-2-yl)-aminocarbonyl}-benzene-sulfonamide 35¾ blend of polyalcohol carboxylic 10 esters and' oil soluble petroleum sulfonates 6¾ xylene . 59¾ The ingredients are combined and ground together in a sand mill to produce particles essentially all below 3 microns. The product can be used directly, extended with oils, or emulsified in water.

EXAMPLE 37 High Strength Concentrate N-{(4,6-dimethoxy-l,3,5-triazin-2-yl)-aminocarbonylJbenzene- sulfonamide 99¾ silica aerogel 0.5% 20 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 conentrate may be formulated further if necessary. - 84 - 4 4 9 8 3 EXAMPLE 38 Low Strength Granule N-i(4,6-dimethoxy-l,3,5-triazin-2-)-aminocarbonylJbenzene- 5-methoxybenzenesulfpnamide 1% 5 Ν,Ν-dimethylformamide 9¾ attapulgite granules 90% (U.S.S. 20-40'mesh).

The active ingredient is dissolved in the solvent and the solution is sprayed upon dedusted granules in a rotating blender. After spraying of 10 the solution has been completed, the blender is allowed to run for a short period and then the granules are packaged.

EXAMPLE 39 Aqueous Suspension N-{(4,6-dimethyl-l53,5-triazin-2-yl)-aminocarbonyl}-benzene-15 sulfonamide 40% Polyacrylic acid thickener 0.3% Dodecylphenol polyethylene glycol ether 0.5% Disodium phosphate 1% Monosodium phosphate 0.5% 20 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. - 85 - 44983 ' EXAMPLE 40 Solution N-{(4-methoxy-6-methyl-l ,3,5-triazin-2-yl)-ami nocarbonyl }-2-chloro-benzenesulfonamide, sodium salt 5% 5 water 95¾ The salt is added directly to the water with stirring to produce the solution, which may then be packaged for use.

EXAMPLE 41 Granule 10 N-{(4,6-dimethoxy-l,3,5-triazin-2-yl)-aminocarbonyl1-2,5- dimethoxybenzenesulfonamide 80¾ wetting agent 1¾ crude ligninsulfo.nate salt (containing 5—20% of the natural sugars) 10% 15 attpulgite 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 adjusted to gently fluidize the material, and a fine spray of water is sprayed onto the fluidized material. The fluidization and 20 spraying are continued until granules of the desired size range are made. The spraying is stopped, but fluidization is continued, optionally with heat, until the water content is 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 25 use. - 86 - **8-β3 EXAMPLE 42 ' t Low Strength Granule N-{(4-methoxy-6-methyl-l,3,5-triazin-2-yl)-aminocarbonyl}-2- chlorobenzenesulfonamide 0.1% 5 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 evaporate 10 the solvent. The material is allowed to cool and then packaged.

EXAMPLE 43 Wettable Powder N-{(4-methoxy-6-me thy1-1,3,5-triazin-2-yl)aminocarbonyl}-2- chloro-5-methoxybenz2nesulfonami de 95% 15 dioctyl sodium sulfosuccinate 0.1% synthetic fine silica 4.9% 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 44 Wettable Powder N-{(4-methoxy-6-methyl-1,3,5-tri azi n-2-yl) ami nocarbonyl}- 2-chlorobenzenesulfonamide 40% sodium ligninsulfonate 20% 25 MontmorilIonite clay 40% - 87 - 449®* 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. the compounds of Formula I can be formulated using the procedures of 5 Examples 15—44.

UTILITY The compounds of Formula I are useful as herbicides. The| may be applied either pre- or postemergence for the control of undesired vegetation in noncrop areas and for selective weed control in certain crops, e.g., 10 wheat. Some of these compounds are useful for the pre- and/or postemergence control of nutsedge in crops such as cotton, corn and rice. By properly selecting rate and time of application, compounds of this invention may be used to modify plant growth beneficially.

The precise amount of the compound of Formula I to be used in any 15 given situation will vary according to the particular end result desired, the use involved, the weeds to be controlled, the soil type, the formulation and mode of application, weather conditions and like factors. Since so i 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 20 invention are uied at levels of e.g. 0.005 to 20 kg/ha with a preferred range of 0.01 to 10 kg/ha. The lower rates of the range will generally be selected for lighter sdils, for selective weed control in crops or in c f situations where liiaximum persistence is not necessary. Some of the compounds of Formula I can be Used at very low rates for plant growth modification, 25 but higher rates may also be useful, depending on factors such as the crop i - 88 - 44983 being treated, timing of treatment, etc.

The compounds of Formula I may be combined with other herbicides and are particularly useful in combination with 3-(3,4-dichlorophenyl)-1,1- dimethyl urea, the triazines such as 2-chloro-4-(ethylamino)-6-(isopropyl- 5 amino)-s-triazine, the uracils such as 5-bromo-3-sec-butyl-6-methyl-uracil, N- (phosponomethyl )glycine, 3-cycl ohexyl -1 -methyl -6-dimethylamino-is-triazine- 2,4(1H, 3H)-dione, N,i’i-dimethyl-2,2-diphenylacetamide, 2,4-dichloro- phenoxyacetic acid (and closely related compounds), 4-ch1oro-2-butyny1- 3-chlorophenylcarbamate (Garbyne^, di-isopropyl thiolcarbamic acid, ester 10 with 2,3-dichloroally'l alcohol (Avadex®), diisopropylthiolcarbamic acid, (R) S-(2,3,3-trichloroallyl)ester (Avadex Avadex is a registered Trade Mark), ethyl-N-benzoyl.-N-(3,,4-dich1oropheny1)-2-aminopropionate (Suffix® ), 1,2-dimethyl-3,5-diphenyl-pyrazolium methyl-sulfate (Avenger® ), methyl 2-(4-(2,4-dichlorophenoxy)-phenoxy}-propanoate (Hoelon®), 4-amino-6-tert-15 butyl - 3 - (methylthio) - 1,2,4 - triazin - 5(4H)-one (Lexone®), 3-(3,4-dichlorophenyl) - 1 - methoxy - 1 - methylurea (Lorox® ), 3 - isopropyl-1H - 2,1,3 - benzothiodiazin-(4)-3H-one 2,2-dioxide, a,a,a-trifluoro-2,6-dinitro-N,N-dipropyl-£-toluidines 1,1 '-dimethyl-4,·4'-bipyridinium ion, monosodium methanearsonate, 2-chloro-2",6''-diethyl(methoxymethyl Jacetanilide, 20 and 1,1 - dimethyl-3-(a,a,a-trifluoro-m-tolyl)-urea (Cotoran a).

The activity of these compounds was discovered in greenhouse tests.

The tests are described and the data resulting from them are shown below.

TEST PROCEDURE Seeds of crabgrass (Digltaria sp.), barnyard-grass (Echinochloa crus-25 gall 1)s wild oats (Avena fatua), Cassia tora, morning glory (Ipomoea sp.), - 89 - V 44.983 cocklebur.(Xanthium sp.), sorghum, corn, soybean, rice, wheat and nutsedge tubers were planted in a growth medium and treated preemergence with the chemicals dissolved in a non-phytotoxic solvent. At the same time, cotton having five leaves (including cotyledonary ones), bush beans with the third 5 trofoliolate leaf expanding, crabgrass with two leaves, barnyardgrass with two leaves, wild.oats with one leaf, cassia with three leaves (including * x cotyledonary ones), morning glory with four leaves (including the cotyle- t donary ones), cocklebur with four leaves (including the cotyledonary ones), sorghum with three leaves, corn with threk leaves, soybean with two cotyle-10 donary leaves, rice with two leaves, wheat with one leaf, and nutsedge with three-five leaves were sprayed. Treated plants and controls were maintained in a green house for 16 days, then all species were compared to controls and visually rated for response to treatment.

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Claims (13)

44983 WHAT WE CLAIM IS:-

1. A compound having the formula: W II Rj—SOz—NH—C—NH—R wherei n 5 R is -/ ) or J N , XN=< \—/ Z R3 is TJ-,ο ./S · C0: /-\ Rs r9 Rio R7 Rs R3 and R6 are independently hydrogen, fluorine, chlorine, bromine, 10 iodine, alkyl of 1—4 carbon atoms, alkoxy of 1—4 carbon atoms, nitro, trifluoromethyl, cyano, CH3S(0)n— or CH3CH2S(0)n—; Ri, 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 15 atoms or alkoxy of 1—2 carbon atoms; Rg is hydrogen, methyl, chlorine or bromine; R9 and R10 are independently hydrogen, methyl, chlorine or bromine; W and Q are independently oxygen or sulfur; n is 0, 1 or 2; - 329 - 44983 X is hydrogen, chlorine, bromine, methyl, ethyl, alkoxy of 1—3 carbon atoms, trifluoromethyl, CH3S— or CH3OCH2—; and t Z is methyl or methoxy; or an agriculturally suitable salt thereof; 5 provided that: a) when R5 is other than hydrogen, at least one of R3, R^, Re and R7 is other than hydrogen and at least two of R3, R^, R6 and R7 must be hydrogen; b) when R5 is hydrogen and all of R3, Ri,, R6 and R7 are other than 10 hydrogen, then all of R3, R^, R6 and R7 must be either chlorine or methyl; and c) when R3 and R7 are both hydrogen, at least one of Ri,, R5 or R6 must be hydrogen.

2. A compound of Claim 1 wherein Rj is -Q-*· 15 rT* wherein R3, Ri,, R5, Rs and R7 are as defined in claim 1.

3. A compound of Claim 2 wherein R3 is hydrogen, fluorine, chlorine, bromine, alkyl of 1—4 carbon atoms, alkoxy of 1—4 carbon atoms, CH3S— or CH3CH2S—; and 20 R5 is hydrogen, flourine, chlorine, bromine or methyl; and R6 is hydrogen, fluorine, chlorine, bromine, alkyl of 1—4 carbon atoms, - 330 - 4*983 alkoxy of 1—4 carbon atoms, trifluoromethyl, nitro, CH3S— or CH3CH2S—; provided that: a) when R5 is other than hydrogen, R3, Ri,, R6 or R7 must independently be hydrogen, fluorine, chlorine, bromine, methyl or methoxy. 5

4. A compound of Claim 3 wherein (a) R is said pyrimidinyl radical; X is methyl or alkoxy having 1—3 carbon atoms; and Z is methyl or methoxy; or (b) R is said triazinyl radical; 10. is methyl or alkoxy of 1—3 carbon atoms; and Z is methoxy.

5. A compound of Claim 4 wherein R3 is hydrogen, fluorine, chlorine, bromine, alkyl of 1—2 carbon atoms, alkoxy of 1—2 carbon atoms, CH3S— or CH3CH2S—; and 15 Ri,, R5 and R7 are independently hydrogen, fluorine, chlorine or methyl; and R6 is hydrogen, fluorine, chlorine, bromine, alkyl of 1—2 carbon atoms, alkoxy of 1—2 carbon atoms, trifluoromethyl, nitro, CH3S— or CH3CH2S—.

6. A compound of Claim 4 wherein 20 R3, Ri,, R5, R6 and R7 are independently hydrogen, fluorine, chlorine or methyl.

7. A compound of Claim 4 wherein R3 is fluorine, chlorine or methyl; and Rim Rg> R'6 and'R7 are independently hydrogen, fluorine, chlorine or 25 methyl; - 331 - .44983 provided that: when R5 is other than hydrogen, Ri* and R5 must be hydrogen.

8. A compound of Claim 4 wherein R3 is fluorine, chlorine or methyl; and 5 R^ and R6 are hydrogen; and R5 and R7 are independently hydrogen, fluorine, chlorine or methyl.

9. A compound of Claim 4 wherein R3 is hydrogen, fluorine, chlorine, bromine, alkyl of 1—4 carbon atoms, alkoxy of 1—4 carbon atoms, CH3S—·, or CH3CH2S—; and

10. A compound of Claim 9 wherein 15 R3 is fluorine, chlorine, bromine, alkyl of 1—2 carbon atoms or alkoxy of 1—2 carbon atoms; and R6 is hydrogen, fluorine, chlorine, bromine, alkyl of 1—2 carbon atoms, alkoxy of 1—2 carbon atoms, trifluoromethyl or nitro. 10 R4, Rs and R7 are hydrogen; and R6 is hydrogen, fluorine, chlorine, bromine, alkyl of 1—4 carbon atoms, alkoxy of 1—4 carbon atoms, trifluoromethyl, nitro, CH3S— or CH3CH2S.

11. A compound of Claim 9 wherein 20 R3 is fluorine, chlorine, bromine, methyl or methoxy; and R6 is hydrogen, fluorine, chlorine, bromine, methyl, methoxy or nitro.

12. A compound of Claim 1 wherein Ra 4 Ra rio ί - 332 - 'i 4 a s 3 where R8, R9 and R10 are as defined in claim 1. 13. A compound of Claim 12 wherein (a) R is said pyrimidinyl radical; Q 1s sulfur; 5. is methyl or alkoxy of 1—3 carbon atoms; and Z is methyl or methoxy; (b) R is said triazinyl radical; Q is sulfur; X is methyl or alkoxy of 1—3 carbon atoms; and 10. is methoxy. I t 14. A compound of Claim 12 wherein Ri is AA »« s and R8 is hydrogen. | 15 15. A compound of Claim 1 wherein Rx is I * and W is oxygen. 16. A compound of Claim 1 which is N-{(4-methoxy-6-methylpyrimidin- 2-yl)ami nocarbonyl1-2-chlorobenzenesulfonami de. 20 17. A compound of Claim 1 which is N{(4,6-dimethoxypyrimidin-2-yl)- ami nocarbonyl}-2,5-dichiorobenzenesulfonamide. 18. A compound of Claim 1 which is N-{(4-methoxy-6-methy1pyrimidin- 2-yl)ami nocarbonyl}-2-methylbenzenesulfonami de. - 333 - t ii 4 9 8 3 ' \ 19. A compound of Claim 1 which is N-{(4,6-dimethylpyrimidin-2-yl)-ami nocarbonyl}-2-thi ophenesulfonami de. 20. A compound of Claim 1 which is N-{(4-methoxy-6-methylpyrimidin- 2-yl)aminocarbonyl}-2-chloro-5-methoxybenzenesulfonamide. 5 21. A compound of Claim 1 which is N-{(4,6-dimethylpyrimidin-2-yl)- aminocarbonyl}-2,6-dichlorobenzenesulfonamide. 22. A compound of Claim 1 which is N-{(4,5-dimethylpyrimidin-2-yl)-aminocarbonyl}-benzenesulfonamide. 23. A compound of Claim 1 which is N-{(4-methoxy-6-methyl-l,3,5- 10 triazi n-2-yl)ami nocarbonyl}-2-chlorobenzenesulfonamide. 24. A compound of Claim 1 which is N-{(4,6-dimethoxy-l,3,5-triazin- 2-yl)ami nocarbonyl}-2-chlorobenzenesulfonamide. 25. A compound of Claim 1 which is N-i(4,6-dimethoxy-l,3,5-triazin- 2-ylJaminocarbonyl}-2,5-dimethoxybenzenesulfonamide. 15 26. A compound of Claim T which is N-{(4,6-dimethoxy-l,3,5-triazin- 2-yl)aminocarbonyl}-benzenesulfonamide. 27. A compound of Claim 1 which is N-{(4-methoxy-6-methyl-l,3,5-triazin-2-yl)aminocarbonyl)-2-chloro-5-methoxybenzenesulfonamide. 28. A compound of Claim 1 which is N-{(4-methoxy-6-methyl-l ,3,5- 20 triazin-2-yl)aminocarbonyl>-benzenesulfonamide. 29. A compound of Claim 1 which is N-ί(4,6-dimethyl-1,3,5-triazin- 2-yl)aminocarbonyl}-benzenesulfonamide. 30. A composition suitable for controlling the growth of undesired vegetation or for use as a growth regulant which comprises an effective 25 amount of a compound of Claim,! and at least one of the following: sur- - 334 - 44983 factant, solid or liquid diluent. 31. The composition of claim 30 which comprises an effective amount of a compound of Claim 2. 32. The composition of claim 30 which comprises an effective amount 5 of a compound of Claim 3. 33. The composition of claim 30 which comprises an effective amount of a compound of Claim 4. 34. The composition of claim 30 which comprises an effective amount of a compound of Claim 5. 35. The compsoition of claim 30 which comprises an effective amount of a compound of Claim 6. 36. The composition of claim 30 which comprises an effective amount of a compound of Claim 7. 37. The composition of claim 30 which comprises an effective amount 15 of a compound of Claim 8. 38. The composition of claim 30 which comprises an effective amount of a compound of Claim 9. 39. The composition of claim 30 which comprises an effective amount of a compound of Claim 10. 40. The composition of claim 30 which comprises an effective amount of a compound of Claim 11. 41. The composition of claim 30 which comprises an effective amount of a compound of Claim 12. 42. The composition of claim 30 which comprises an effective amount 25 of a compound of Claim 13. - 335 - 44983 \ = 43. The composition of claim 30 which comprises an'effective amount of a compound of Claim 14. 44. The composition of claim 30 which comprises an effective amount of a compound of Claim 15. 45. The composition of claim 30 which comprises an effective amount of the compound of Claim 16. 46. The composition of Claim 30 which comprises an effective amount of the compound of Claim 17. 47. The composition-of Claim 30 which comprises an effective amount 10 of the compound of Claim 18. 48. The composition of Claim 30 which comprises an effective amount of the compound of Claim 19. 49. The composition of Claim 30 which comprises an effective amount of the compound of Claim 20. 50. The composition of Claim 30 which comprises an effective amount of the compound of Claim 21. 51. The composition of Claim 30 which comprises an effective amount of the compound of Claim 22. 52. The composition of Claim 30 which comprises an effective amount 20 of the compound of Claim 23. 53. The composition of Claim 30 which comprises an effective amount of the compound of Claim 24, 54. The composition of Claim 30 which comprises an effective amount of the compound of Claim 25. 55. The composition of Claim 30 which compHses an effective amount - 336 - \ 4*983 of the compound of Claim 26. 56. The composition of Claim 30 which comprises an effective amount of the compound of Claim 27. 57. The composition of Claim 30 which comprises an effective amount 5 of the compound of Claim 28. 58. The composition of Claim 30 which comprises an effective amount of the compound of Claim 29. 59. The composition of Claim 30 substantially as illustrated in any of Examples 15—44. 10 60. 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 1. 61. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a 15 compound of Claim 2. 62. 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 3. 63. A method for controlling the growth of undesired vegetation which 20 comprises applying to the locus to be protected an effective amount of a compound of Claim 4. 64. 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 5. 25 65. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a - 337 - 66. 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. 449β3 compound of Claim 6. 5 67. 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 8. 68. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a 10 compound of Calim 9. 69. 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 10. 70. A method for controlling the growth of undesired vegetation which 15 comprises applying to the locus to be protected an effective amount of a compound of Claim 11. 71. 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 12. 20 72. 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 13. 73. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a 25 compound of Claim 14. - 338 - 4*983 74. 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 15. 75. A method for controlling the growth of undesired vegetation which 5 comprises applying to the locus to be protected an effective amount of a compound of Claim 16. 76. 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 17. 10 77. 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 18. · 78. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a 15 compound of Claim 19. 79. 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 20. 80. A method for controlling the growth of undesired vegetation which 20 comprises applying to the locus to be protected an effective amount of a compound of Claim 21. 81. 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 22. 25 82. A method for controlling the growth of undesired vegetation which - 339 - 44983 comprises applying to the locus to be protected an effective amount of a compound of Claim 23. 83. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a 5 compound of Claim 24. 84. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a i compound of Claim 25. 85. A method for controlling the growth of undesired vegetation which 10 comprises applying to the locus to be protected an effective amount of a compound of Claim 26. 86. 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 27. 15 87. 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 28. 88. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a 20 compound of Claim 29. 89. A method for selectively controlling the growth of nutsedge, Cyperus. spp.^ in crops which comprises applying to the locus of the area to be controlled an effective amount of a compound of Claim 1. 90. The method of claim 89 which comprises applying an effective 25 amount of a compound of Claim 2. Ί - 340 - 4*98 3 91. The method of claim 89 which comprises applying an effective amount of a compound of Claim 3. 92. The method of claim 89 which comprises applying an effective amount of a compound of Claim 4. 93. The method of claim 89 which comprises applying an effective amount of a compound of Claim 5, 94. The method of claim 89 which comprises applying an effective amount of a compound of Claim 6. 95. The method of claim 89 which comprises applying an effective 10 amount of a compound of Claim 7. 96. The method of claim 89 which comprises applying an effective amount of a compound of Claim 8. 97. The method of claim 89 which comprises applying an effective amount of compound of Claim 9. 98. The method of claim 89 which comprises applying an effective amount of a compound of Claim 10. 99. The method of claim 89 which comprises applying an effective amount of a compound of Claim 11. 100. The method of claim 89 which comprises applying an effective 20 amount of a compound of Claim 12. 101. The method of claim 89 which comprises applying an effective amount of a compound of Claim 13. 102. The method of claim 89 which comprises applying an effective amount of a compound of Claim 14. 103. The method of claim 89 which comprises applying an effective amount of a compound of Claim 15. - 341 - A4983 104. The method of claim 89 which comprises applying an effective amount of the compound of Claim 17. 105. The method of claim 89 which comprises applying an effective amount of the compound of Claim 21. i 5 106. A method for selectively controlling the growth of undesired vegetation in wheat comprising applying to the locus of such undesired vegetation an effective amount of a compound of Claim 1. 107. The method of claim 106 comprising applying an effective amount of a compound of Claim 2. 108. The method of claim 106 comprising applying an effective amount of a compound of Claim 3. 109. The method of claim 106 comprising applying an effective amount of a compound of Claim 4. 110. The method of claim 106 comprising applying an effective amount 15 of a compound of Claim 5. 111. The method of claim 106 comprising applying an effective amount of a compound of Claim 6. 112. The method of claim 106 comprising applying an effective amount of a compound of Claim 7. 113. The method of claim 106 comprising applying an effective amount of a compound of Claim 8. 114. The method of claim 106 comprising applying an effective amount of a compound of Claim 9. 115. The method of claim 106 comprising applying an effective amount 25 of a compound of Claim 10. - 342 - 4 <3 0 a 3 4 116. The method of claim 106 comprising applying an effective amount of a compound of Claim 11. 117. The method of claim 106 comprising applying an effective amount of a compound of Claim 12. 118. The method of claim 106 comprising applying an effective amount of a compound of Claim 13. 119. The method of claim 106 comprising applying an effective amount of a compound of Claim 14. 120. The method of claim 106 comprising applying an effective amount 10 of a compound of Claim 15. 121. The method of claim 106 which comprises applying an effective amount of the compound of Claim 20. 122. The method of claim 106 which comprises applying an effective amount of the compound of Claim 23. 123. The method of claim 106 which comprises applying an effective amount of the compound of Claim 24. 124. The method of claim 106 which comprises applying an effective amount of the compound of Claim 25. 125. A method for controlling the growth of water hyacinth which 20 comprises applying thereto an effective amount of a compound of Claim 1. 126. The method of claim 125 which comprises applying an effective amount of a compound of Claim 9. 127. The method of claim 125 which comprises applying an effective amount of the compound of Claim 16. 25 128, The method of claim 125 which comprises applying an effective - 343 - amount of the compound of Claim 23. 129. The method of claim 125 which comprises applying an effective amount of the compound of Claim 26. 130. The method of claim 125 which comprises applying an effective 5 amount of the compound of Claim 27. 131. A method for regulating the growth of vegetation which comprises applying to the locus of the vegetation an effective amount of a compound of Claim 1. 132. The method of claim 131 which comprises applying an effective 10 amount of a compound of Claim 9. 133. The method of claim 131 which comprises applying an effective amount of the compound of Claim 17. 134. The method of claim 131 which comprises applying an effective amount of the compound of Claim 22. 135. The method of claim 131 which comprises applying an effective amount of the compound of Claim 23. 136. The method of claim 131 which comprises applying an effective amount of the compound of Claim 26. 137. The method of claim 131 which comprises applying an effective 20 amount of the compound of Claim 28. 138. The method of claim 131 which comprises applying an effective amount of the compound of Claim 29. 139. The method of claim 60, substantially as described herein. 140. The method of claim 89, substantially as described herein. 141. The method of claim 106, substantially as described herein. - 344 - 44983 142. The method of claim 125, substantially as described herein. 143. The method of claim 131, substantially as described herein. 144. A compound of claim 1 substantially as hereinbefore described with reference to Examples 1—7 and 9—14. 5 145. A method of making a compound of Claim 1 which comprises reacting a compound of formula RiS02NCW (II) with a compound of general formula NH2—R (III) 10 wherein Ri, W, X, Z and R are as defined in claim 1. 146. The method of Claim 145 wherein the reaction is carried out in an inert aprotic organic solvent at ambient pressure and temperature. 147. The products of reacting compounds of general formulae (II) and (III) as defined in Claim 145. 15 148. A method for controlling the growth of undesired vegetation or for regulating the growth of vegetation which comprises applying to the ' locus of the vegetation an effective amount of a compound of Claim 147. 149. A composition suitable for controlling the growth of undesired vegetation or for use as a growth regulant which comprises an effective 20 amount of a compound of claim 147 and at least one of the following: surfactant, solid or liquid diluent. 150. The method of Claim 145, substantially as hereinbefore described with reference to Examples 1—7 and 9—14. - 345 - 449s3 CRUICKSHANK & CO., Agents for the Applicants, Ypughal House,

13. , Trinity Street, Dublin 2. - 346 -