FI70577C - N- (HETEROCYCLISK-AMINOCABONYL) - ARYL SULPHONAMIDER ANVAENDBARA SOM HERBICHIDER OCH VAEXTERNASTILL VAEXTREGULERANDE AEMNEN - Google Patents

Description

ΓΒ1 ^ ADVERTISEMENT PUBLICATION ππς ^ π LBJ (11) utlägg ni ngsskrift / Uo / (c (45) f: ·· 1 b 1 · -a-vlty ^ ^ ^ (51) Kv.ik. * / Lnt.ci. * c 07 D 239 / ^ 2, 251/1 * 4, * 405/1 2, '' * 409/12, A 01 N * 43/5 * 4, * 43/66 SUO MI —Fl NL AN D (21 ) Patent application - Patontansökning 771123 (22) Date of application - Ansökningsdag ni «r __ / ci \ /, UM · 7 * V / (23) Starting date —Giltighetsdag g ^ g ^ (41) Published public - Blivit offentlig gg ^

National Board of Patents and Registration Date of display and publication—. -

Patent and registration authorities '' Ansökan utlagd och utl.skriften publicerad Uo.0b.o6 (86) Kv. application - Int. trap (32) (33) (31) Claim claimed - Begärd priority 07.0 * 4.76 23.02.77, 23.02.77 USA 67 * t668, 769913 76991 ** '(71) E.l. du Pont de Nemours and Company, Wilmington, Delaware 19898, USA (72) George Levitt, Wilmington, Delaware, USA (7 * 4) Oy Kolster Ab (5 * 4) As herbicides and plant growth regulator i ;. N- (heterocyclic aminocarbonyl) arylsulfonamides to be used - N- (heterocyclic aminocarbonyl) -arylsulfonamides and other herbicides and other tertiary esters

The invention relates to N- (heteroskk-1 inen-Amin o k a r b o n y y 1 L) -aryl isulfone lam 1 rl i t for use in agriculture.

In French pat ent no. 1 6H 71 / discloses female para-substituents which are phenylsulfone ianides which are useful as antidiabetic agents (as medicaments for diabetes): _ 0 h - // \\ - 3 C- MI ϊ - C - NH - so that R is H, halogen, CT or alkyl.

Loyernann et. ai. , That. Aio, tl, 1H ij 6 7 p (1 k k 9), show a series of sulfeniam iuJe-ί a which are used, e.g., i 1 i-j derivative 1 s ia and compounds having the naava:

H 30.NHCNHR

wherein R is butyl, phenyl or (\ r) a R. en hydrogen or methyl.

Rl 70577

When tested for their effect on hypoglycemia in rats (doses of 2b mg / 100 g orally), compounds in which R is butyl and phenyl were the most effective. Others were ineffective or inactive.

Wojciechowski, J. Acta. Polo. Pharm. 19, pp. 121-5 (1962) / Chem. Av., 59 1633 e.7 describes the synthesis of N-Z- (2,2-dimethoxypyrimidin-4-yl) aminocarbonyl_7-1 * -methylbenzenesulfonamide: OCHa

Based on similarity to a known compound, the factor predicted the effect of the disclosed compound on blood glucose deficiency.

Dutch patent 121,788, published September 15, 1966, teaches the preparation of compounds of formula (i) and their use as general or selective herbicides, /qVsq.hhcii-0 (i) in7 ItHKl

Ha wherein R 1 and R 2 may independently be alkyl of 1 to 4 carbon atoms; and R 1 and R 2 may independently be hydrogen, chlorine or alkyl of 1 to 4 carbon atoms.

The compounds of formula (ii) and their use as antidiabetic agents are described in J. Drug Res. 6, 123 (1974).

ö \ "(11)

SOaNHCNHR

11 3 70577 wherein R is pyridyl.

The presence of an unwanted plant.il is nude n causes substantial damage to beneficial plants, especially agricultural products that meet the needs of human staple food and fiber such as cotton, rice, corn, wheat, soybeans, etc. fiber shortages require improvements in the production efficiency of these growths. To prevent or reduce the loss of some of such valuable plants by killing or inhibiting the growth of unwanted vegetation is one way to improve this efficiency.

There are a wide variety of agents available that are useful for killing or preventing (combating) the growth of unwanted vegetation, such agents are commonly referred to as herbicides. However, there is a need to find even more effective herbicides that eradicate or control weeds without causing significant damage to beneficial plants. Some weeds (especially the nutcracker in particular) are very difficult to control; Many of the herbicides used to control nutcrackers are so non-selective that they cause damage to the plants themselves.

According to the present invention there are provided novel compounds of formula I and their agriculturally acceptable salts, suitable agricultural combinations containing them and methods for their use as selective as well as common herbicides which are effective both before and after emergence. These compounds are very effective herbicides. They are particularly useful in controlling nutcrackers and the damage they cause to desired crops such as cotton, rice, corn, wheat, etc. is negligible.

W

R1-SO2-NH-C-NII-R I.

wherein R is: N / or N -S

O, Q 1 is H 3 R 4

K '· * 3/3 ifrS

PY \% Hg R10 „70577

R 9 is hydrogen, fluorine, chlorine, bromine, iodine, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, nitro, trifluoromethyl, cyano, CH 2 S (O) - or CH 2 CH 2 S or CH 3 CH 2 SO 2; R 1 is hydrogen, fluorine, chlorine, nitro or methyl;

Rg is hydrogen, fluorine, chlorine, methyl or methoxy;

R 9 is hydrogen, fluorine, chlorine, bromine, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, nitro, trifluoromethyl, cyano or CH 2 SO 2); R 7 is hydrogen, fluorine, chlorine, C 1 -C 4 alkyl or C 1 -C 4 alkoxy,

Rg is hydrogen, methyl or chlorine;

Rg is hydrogen, chlorine or bromine; R 1g is hydrogen, chlorine, bromine or methyl; W and Q are independently oxygen or sulfur; n is 0, 1 or 2; X is hydrogen, chlorine, bromine, methyl, ethyl, alkoxy of 1 to 3 carbon atoms, trifluoromethyl, CH 2 S 5 or CH 2 OCH 6 -; and Z is methyl or methoxy; or their agriculturally acceptable salts; provided that a) when Rg is other than hydrogen, at least one of Rg, R1, Rg and Ry is other than hydrogen and at least two of Rg, Rg and R? is hydrogen; b) when Rg is hydrogen and none of Rg, R1, R8 and R8? is not hydrogen, so must all the groups R, R ^, Rg and R? be either chlorine or methyl; and c) when Rg and R? are each hydrogen, at least one of R 1, R 8 or R 8 must be hydrogen.

Preferred in ascending order of preference, based on efficacy or cost, or both, are 1) those compounds of formula I as defined above, wherein R 1 is V <- r \ R.

R.7 R6 2) compounds of most preferred 1) wherein Rg is hydrogen, fluorine, chlorine, bromine, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, CH2S- or CH2CH2S-; and R 1 is hydrogen, fluorine, chlorine, bromine, laxyl; and

R 9 is hydrogen, fluorine, chlorine, bromine, alkyl of 1 to 4,70577 carbon atoms, alkoxy of 1 -4 h 1 1 L 1 O, trifluoromotyl, nitro, CH 2 S- or Cl 2 CH 2 S-; e del 1 y t Laon that: а) when it is other than hydrogen, the groups R 1, R 2, R 1 or R 1 must be hydrogen, fluorine, chlorine, bromine, methyl or methoxy; 3) compounds of Most Preferred 2 wherein (a) R is a pyridinidinyl radical; X is methyl or alkoxy of 1 to 3 carbon atoms; and Z is methyl or methoxy; or (b) R is a triazinyl radical; X is methyl or alkoxy of 1 to 3 carbon atoms; and Z is methoxy; 4) most preferred 3) compounds having hydrogen, fluorine, chlorine, bromine, alkyl of 1-2 carbon atoms, alkoxy of 1-2 carbon atoms, CH 2 S- or CH 2 CH 2 S-; and R 1, R 2 and R 4 are independently hydrogen, fluorine, chlorine or methyl; and

R 9 is hydrogen, fluorine, chlorine, bromine, alkyl of 1 to 2 carbon atoms, alkoxy of 1 to 2 carbon atoms, trifluoromethyl, nitro, CH 2 S or CH 2 CH 2 S; 3) most preferred 3) compounds wherein R 1, R 2, R 6 -, R 8 and R 2 are independently hydrogen, fluorine, chlorine or methyl; б) most preferred 3) compounds wherein R 1 is fluoro, chloro, or methyl; and R 1, R 8, R 2. and are independently hydrogen, fluorine, chlorine or methyl; provided that: when R g is other than hydrogen, R m and R g must be hydrogen; 7) most preferred 3) compounds wherein R 1 is fluoro, chloro or methyl; and R 1 and R 8 are hydrogen; and

Rg and R? are independently hydrogen, fluorine, chlorine or methyl; 8) most preferred 3) compounds wherein R 1 is hydrogen, fluorine, chlorine, bromine, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, CH 2 S or CH 2 CH 2 S-; and R 1, R 8 and R 4 are hydrogen; and

R 9 is hydrogen, fluorine, chlorine, bromine, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, trifluoromethyl, nitro, CH 2 S or CH 2 CH 2 S; 9) most preferred 8) compounds wherein R 1 is fluoro, chloro, bromo, alkyl of 1-2 carbon atoms or alkoxy of 1-2 6 70577 carbon atoms; and

Rp. is hydrogen, fluorine, chlorine, bromine, alkyl having 1-2 carbon atoms, alkoxy having 1-2 carbon atoms, trifluoromethyl or nitro; and 10) most preferred 8) compounds having fluorine, chlorine, bromine, methyl or methoxy; and

Rj. is hydrogen, fluorine, chlorine, bromine, methyl, methoxy or nitro.

Also preferred in ascending order of preference based on efficacy or cost, or both: A) those compounds of formula I as defined above wherein R is:

jr \ or jtL

B) most preferred compounds of A) wherein (a) R is a pyrimidinyl radical; Q is broken; X is methyl or alkoxy of 1 to 3 carbon atoms; and X is methyl or methoxy; and R is a triateyl radical; Q is broken; X is methyl or alkoxy of 1 to 3 carbon atoms; and Z is methoxy; C) most popular A) compounds in which:

Rj_ is Π Λ and Rg is hydrogen.

Rq'Ns A

Similarly, on the basis of efficacy, those compounds of formula I as defined above are preferred in which: R 1 is

Particularly advantageous in terms of their striking efficiency and very low price or both are:

II

V 70577 1) N-7 (4-methyl-8-methylpyrimino-2-yl) Ninocarbonyl-2-chlorobenzenesulfonylamide, m.p. 194-196 ° C; 2) N- [2- (4,6-dimethoxypyrimidin-2-yl) aminocarbonyl] -2,5-dichlorobenzenesulfonamide, m.p. 189-190 ° C ·, 3) N-7- (4-methoxy-6-methylpyrimidin-2-yl) aminocarbonyl] -2-methylbenzene Ulfonamide, m.p. ? 17 -174 ° C; and 4) M-7- (4,6-dimethylpyridin-2-yl) aminocarbonyl-17-2-thiophenesulfonamide, m.p. 224-228 ° C.

5) N-7- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) aminocarbonyl-1,2-chlorobenzenesulfonamide, m.p. 174-17 ° C; 6) N-ZX4,6-dimethoxy-1,3,5-triazin-2-yl) aminocarbonyl-2-chlorobenzenesulfonamide, m.p. 188-189 ° C; and 7) N-7- (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 herbicides, not all of them are selective for all plants. However, by selecting specific compounds, weed control and plant safety are achieved. Thus, some compounds are particularly selective for weed control in wheat and rice; to control nutcrack in plants such as maize, cotton, soybeans or rice cakes; and combating water hyacinth. In addition, the compounds of formula I are useful plant growth regulators, e.g. by increasing the sugar content in sugar cane and millet and by suppressing the formation of seed heads in grasses such as Bahia grass.

Particularly preferred A) for the selective control of weeds in wheat are: 1) N-7- (4-methoxy-6-methylpyrimidin-2-yl) aminocarbonyl-2-chloro-5-methoxybenzenesulfonamide, m.p. 199-200 ° C; 2) N- (X 4-methoxy-6-methyl-1,3,5-triazin-2-yl) aminocarbonyl] -2-chlorobenzenesulfonamide, m.p. 174-178 ° C; 3) N - Z "(4,6-dimethoxy-1,3,5-triazin-2-yl) aminocarbonyl] -2-2-chlorobenzenesulfonamide, m.p. 188-189 ° C; and 4) NZ (4 (6-dimethoxy-1,3,5-trialsin-2-yl) aminocarbonyl] -2,5-dimethoxy-ibontoene sulfone is mp 187-18 ° C.

β 70577 β) for the selective control of nut crust in plants are: 1) Ν-Λ4, b-dimethoxy ipyrrine di n-2-yy1i) aminocarbonyl117-2,5-di chloro ben Tsuen isu] f is i ami d i., sp . 189-190 ° C · and 2) N - [(4,6-dimethylpyridin-2-yl) aminocarbonyl] -2,6-dichlorobenzenesulfonamide, m.p. 177-182 ° C; C) for the control of water hyacinth are : 1) Ν-Γ (4-mc-thiol; i - Π-methyl pyrimidin-2-yl) aminocarbonyl] -2-chlorobenzenesulfonamide, mp 194-196 ° C; 2) d- / ~ ( 4- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) aminocarbonyl] -2-chlorobenzenesulfonamide, mp 174-178 ° C; (4, B - d ime toks i -1, 3, 9-1. Ri at s in - 2 - yy 1 i) aminocarbonyl 1 i] - benzenesulfonamide, m.p. 18 3-185 ° C; and 4) N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) aminocarbonyl] -2-chloro-3-methoxybenzenesulfonamide, m.p. 175-176 ° C *, D) growth regulators are: 1) N-Z 1 (4,6-dimethylpyrimidin-2-yl) aminocarbonyl-7-benzene sulfonamide: m.p. 228-230 ° C; and 2) N-ZX 4,6-dimethoxy-pyramidin-2-yl) aminocarbonyl-7- to 2,5-dichlorobenzenesulfonamide, m.p. 189-190 ° C.

3) N - 7 (4, b-dimethoxy-1,3,3-triazin-2-yl) aminocarbonyl-17-benzenesulfonamide, m.p. 183-185 ° C; 4) N-7 (4-methoxy-methyl-1,3,5-triazin-2-yl) aminocarbonyl-7-benzene sulfone Laini di ·, 5) N - 7 (4,6- dimethyl-1,3,8-triazin-2-yl) aminocarbonyl-7-benzenesulfonamide, m.p. 200-201 ° C and δ) N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) aminocarbonyl] -2-chlorobenzenesulfonamide, m.p. 174-178 ° C.

E) for the selective control of weeds in rice are: 1) N - [(4-methylpyrimidin-2-yl) aminocarbonyl] -2-chlorobenzenesulfonamide, m.p. 201-203 ° C; and 2) N-Li 4 (G-dimethoxypyridin-2-yl) aminocarbonyl] -2,5-dibromobenzenesulfonamide, mp 20-1204 ° C.

F) for the selective control of vesicles is: 1) M - / "(4,6-di; triethoxy -1,3,3-1-triazin-2-yl) aminocarbonyl] benzene 1 mp 18 3-18 b ° C.

Synthesis

As shown in Equation 1, compounds of formula I can be prepared by reacting the appropriate 2-aminopyrimidine or 2-amino-1,3,5-9,70577 triazine of formula III with the appropriate substituted sulfonyl isocyanate or isothiocyanate. of formula II; wherein, W, X, Z and R are as defined above.

Equation 1

W

R1SO2NCW + NH2-R -> R1SO2 NHCNH-R

(II) (III) (I)

The reaction is preferably carried out in inert aprotic organic solvents such as methylene chloride, tetrahydrofuran or acetonitrile at ambient pressure and temperature. The method of addition is not decisive; however, it is often convenient to add the sulfonyl isocyanate or isothiocyanate to the stirred suspension of amine III. Since such isocyanates and isothiocyanates are usually liquids, their addition can be easily adjusted.

The reaction is usually exothermic. In some cases, the desired product is insoluble in the warm reaction medium and crystallizes therefrom 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 1-chlorobutane or ethyl ether, and filtration.

In certain cases, it is possible that the reaction shown in Equation 1 above results in isomeric compounds which are formed to a small extent in the addition reaction of compound II to the enaocyclic nitrogen atoms of amine III.

The following are examples of their structural formulas: 10 70577 Λ Η ϊ \ ν

R1SOaNHC-I ^ J> -X, ^ SOatlHC-lt ^ -Z

ζ w ΝΗ II Μ ta] Hi-SOsNHC-IT ^^ ir

X

It is to be understood that the reaction products obtained from the addition of a compound of formula II to exocyclic amines III as well as to endocyclic nitrogen atoms are to be considered as part of this invention.

Intermediate sulfonyl isocyanates of formula II (wherein W is 0) can be prepared by reacting the corresponding sulfonamides with phosgene in the presence of n-butyl isocyanate under reflux in a solvent such as chlorobenzene, H. Ulrich and A.A.Y. Sayigh, Newer Methods of Preparative Organic Chemistry Vol. VI pp. 223-241, Academic Press, New York and London, W. Foerst Ed. methodically, in cases where the desired sulfonyl isocyanate is formed in a low yield using the disclosed method, the sulfonylurea formed by the reaction of butyl isocyanate with the appropriate sulfonamide can be reacted with phosgene as described in the above reference.

The preparation of sulfonamides from ammonium hydroxide and sulfonyl chlorides has been extensively described in the literature, e.g., Crossley et al., J. Am. Chem. Soc., 60, 2223 (1938). The preparation of 2-furanesulfonamide is described in J. Org. Chem., 18, 894 (1953).

Certain sulfonyl chlorides are preferably prepared by chlorosulfonation of a substituted benzene, naphthalene or thiophene in carbon tetrachloride according to the method of H. T. Clarke et al., Org. Synth. Coll. Volume 1, Second Edition 1941, p. 85, in accordance with doctrines. Other benzenesulfonyl chlorides of benzene 70577 are preferably prepared by diazotization of the appropriate uniline sodium nitrite in 1 L of HCl, followed by reaction of the diazonium salt with sulfur dioxide and cuprous chloride in acetic acid H.L. Yale and F. Sowinski, J. Org. Chem., 25, 1824 (1960).

Furanesulfonyl chlorides are preferably prepared as shown in Equation 2.

Equation 2 "Haö / HOl> fl \ (C0> so2ci

Sulfonyl isothiocyanates can be prepared by treating sulfonamides with sulfur carbon and potassium hydroxide, followed by reaction of the dipotassium salt with phosgene K. Hartke’nj Arch. Pharm., 299, 174 (1966).

The synthesis of heterocyclic amine derivatives is described in "The Chemistry of Heterocyclic Compounds", a series published by Interscience Pub., New York and London. 2-Aminopyrimidines have been described by D. J. Drown in "The Pyrimidines", Vol., XVI.

The agriculturally acceptable salts of the compounds of formula I are also useful herbicides and can be prepared in many ways known in the art. For example, metal salts can be prepared 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 prepared by similar methods.

Salts of the compounds of formula I can also be prepared by exchanging one cation for another. The cation exchange can be carried out by directly treating an aqueous solution of a salt of a compound of formula I (e.g. an alkali metal or quaternary amine salt) with a solution containing the cation to be exchanged. This method is particularly effective when the desired salt containing the exchanged cation is insoluble in water.

7057V

I do and can be separated nuodalt.imaila.

The exchange can also be carried out by passing an aqueous solution of a salt of a compound of formula I (e.g. an alkali metal or k. Vernary salt thereof) 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 the cation of the original salt and the desired product is eluted in a column. This method is particularly useful when the desired salt is soluble in water.

Acid addition salts useful in this invention can be obtained by reacting a compound of formula I with a suitable acid, e.g., p-toluenesulfonic acid, trichloroacetic acid, and the like.

The compounds of this invention and their preparation are described in more detail in the following examples in which the temperatures of stallions are given in degrees Celsius.

Example 1 N - Z - (1,6-Dimethylpyrimidin-2-yl) aminocarbonyl 1,7 Benzene sulfonamide

To a dry, well-stirred mixture of 12.4 g of 2-amino-4,6-dimethylpyrimidine in 250 ml of methylene chloride was added dropwise at ambient temperature and pressure 18.3 g of benzenesulfonyl isocyanate. The resulting mixture was stirred for 2 hours and the precipitated product was removed by filtration. After washing, 1-chlorobutane had a melting point of 228-230 ° of the product and gave characteristic absorption bands in the infrared chain of 1710 cm at 1620 and 1550 em. The product was N - [(4,6-dimethylpyrimidin-2-yl) aminocarbonyl] benzenesulfonamide.

Example 2 N- [4- (4-Methoxy-6-methyl-pyrimidin-2-yl) -aminocarbonyl] -2-2-chloro-benzenesulfonamide

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-chloro-benzenesulfonyl-cyanocyanate with stirring. The resulting mixture was stirred for 16 hours, cooled to 10 ° and filtered through Lett to give 470 g of a solid which melted at 1.05-196 °. Mnssaspektro-Graf analysis showed that the molecular weight of this product was 356. Analysis i:

Calcd for CINC 2 O 5 S: C, 4, 80%; H, 4.40%; N, 15.75%; Found: C, 4 3, 4 7%; H, 3.56 N, 15.30%.

This product was N - [(4-methoxy-6-methylpyrimidin-2-yl) amin-70577] carbonyl-1H-2-clone ben Lseon i su lion i ..iiii'i cl i.

Evaporation of the filtrate to a smaller volume gave 20 g of by-product, m.p. 160-162 °. The infrared absorption book of the by-product was similar to that of the first precipitate and had a molecular weight of 356.

Analysis:

Calculated: C, 3 H and 3 ClNO (O 2 S: C, 43.80 ° O, H, 3.40 N, 15.75%; Found: C, 44.09 X; H, 3.56 X, N, 14.97 X.

Using an equivalent amount of the appropriate 2-aminopyrimidine and an appropriately substituted benzenesulfonyl isocyanate, the following compounds of formula I can be prepared by the methods of Examples 1 or 2: 1. 70577

Table I-A

\ / R / CH3 "ζ * o" /

Atj ------ 3 \ oC ^ NHCNH- ^.)

\ 'CH

R4 R3 LH3 F R R I? R s p.

r'3 4 1 b 7 p H H H H H 7? 8 -? 31 F H H H H 718-719 CH3 H H H H 19 5-19 p

Cl H H H H 2U4-205 H H H NO ,, H 19 3-196 H H H 0Γ3 H 183 (U) H Cl H H H 142-143 -CF3 H H H H 218-222 CH 0 H H CH.S0o H 300-203 (d)

ChT30- H CHO- H H 198-199 CH3 H H N0? H 191-192 CH0 H H -CH (CH2) „H 157-162

O ö Z

CHq H H Cl H 709-211

Cl H H CH H 211-213 F H H F H 189-190 CH30- H H CH3 H 193-194

Cl H H H CH 2 3 G - 2 3 7 NO. H Cl H H 710-212 «i

Cl H H II Cl 177-18 2 F H H H F 228-211

Cl Cl Cl H H 315-217

Cl H Cl Cl H 294-205 -CH (CH 2). H Cl -CH (CH3) 7H 131-136 70577 1 5 R3 R, 4 Rb R6 R7 Sp 'C H SO ,, - - H H H H rubber Z O z

CH3SO2- h H h h 2 08 -2 1 U

CH H CH H CH ,. 227-231 (d)

O vJ

F H F H F 173-182

Cl H Cl H Cl 288-210 CH30- H CH30- H CH 0- 192-193

Cl Cl H Cl Cl 220-222 CH3 CH3 H CH3 CH3 2 4 0-21 (6

Cl Cl H H H 195-197

Cl CH3 H H H 196-199 CH30- Cl H H H 179-180 F Cl H H H 196-197 CH3 Cl H H II 708-209

Cl H Cl H H 202-225 F H Cl H H 202-203 H Cl Cl H H 210-212 'H Cl H Cl H 199-202 CH30 H Cl CH30 H 202-203 F H H CH3 H 210-212 CH3 H H F H 200-201

Cl H H CH 3 ° - H 198-199

Br HH Br H 211-212 CH30- HH ch3 ° - H 193-195 CH3 HH CH3 H 204-275 CH3 HH Br H 205-207 C „H 0- HHC, H10- H 208-210 / 5 2 b CH30- HHFH 199-201

Cl H H Cl H 212-213 CH,} CH2CH2 O H H CH3CH2CH2OH 150-152 CH., 0- H H Cl H 209-210 CH1 CH ,, H NOo H 2 2 1- 2 2 3 O J z 70577

1 G

Table I-B

R6 k - N - <7 0 N, / ° CH3

R. - -oCR.NHCNH

V: - <2 vy k k k_k_r5 r6_k_SP- H H H H H 204-205 H CH3 H H H 149-151

Br H H H H 210-211 F H H H H 198-199 CH30 H H H H 178-180 CH3 H H H H 172-174

Cl H H H H 206-207 CN H H H H 154-156 -SO2CH3 H H H H 170-171 H Cl H H H 151-153 H H H CH3 H 150-152

Cl H H CN H 203 - 205 (d) CH 3 H H ~ SO 2 CH 3 H 182-184

Cl Cl H H H 199-200

Cl CH3 HHH 177-186 CH30- Cl HHH 190-193 CH Cl HHH 190-192 F Cl HHH 193-195 H Cl Cl HH 193-195 nC ^ HgO- HH n-C4HgO- H 182-183 FH Cl HH 206- 208 NOg HHHH 223-225 CF3 HHHH 194-197

Cl H F H H 199-201

Cl H Cl H H 195-197

Cl H CH30 HH 201-202 CH3 Cl H Cl H 187-189 CH3Q H CHgO HH 182-184 70577 _N __ ^ 7_Sp 'HH CH30 NO2 H 211-213 H Cl H Cl H 207-211 H CH3 CH3 HH 193-196 FHHFH 177-178 CH30- HH Cl H 199-200 CH3 HH Cl H 206-207 C „HcO- HHC„ H O- H 175-177

Cl H H CH3 H 197-200 CH3 H H NO2 H 194-195 CH3 H H -CH (CH3) 2 H 136-142

Cl H H NO 2 H 178-180 CH 3 H H CH 3 H 174-176 CH H H Br H 195-197

O

Br H H Br H 207-209 CH 0- H H CH O- H 175-177

o O

Cl H H Cl H 174-179 F H H CH3 H 207-208 CH3 H H F H 173-175

Cl H H CH3 ° - H 199-200 CH30- H H CH3 H 180-182 F H H H F 192-195

Cl H H H Cl 148-153

Cl H H H CH3 166-170 CH3SO2- H H H H 170 C H SO - H H H H rubber 2-0 L ·.

CH3S- H H H H 200-202 C „H 0- H H Cl H 180-183 2 5 CH30 H Cl CH30 H 173-175 CH3CH2CH2O H H CH3CH2CH2O H 173-175 CH3S H H Cl H 215-216 CH3 CH3 H NO2 H 191-193

Cl Cl Cl H H 186-187

Cl H Cl Cl H 189-190 CH3 H CH3 H CH3 203-205 18 70577 _ ^ 4__SP ‘F H F H F 197-199

Cl H Cl H Cl 181-186 CH 3 O- H CH 3 O - H CH 3 O 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 H NO2 H 182-183

Table I-C

V. R:

'2 / -N V

R - (/ CO NHCNH - (5 \ - - / 2 NC17 / \ X o c1] V r3 ocj3 _R5 R6_R7 SP · H H H H H 202-203 F H H H H 200-201

Cl H H H H 179-181 CH3 H H H H 185-186 CH3SO2 H H H CH3 200-202.5 SO2C2H5 H H H H rubber H Cl H H H> 250 H H H CF3 H 190-191

Cl H H CN H 215-217 F H H H F 213-215

Cl H H H Cl 192-194 NO2 H Cl H H 196-198 NO H H H H 219-220 CH3S H H Cl H 211-213 CH 0- Cl H H H 183-184 0 F Cl H H H 244-245 F H Cl H H 223-2 24

Cl H F H H 203-205

Cl H Cl li H 190-191 CH30- H C H 3 ° - H H 182-184 19 70577 R0 R., Rc Rr R „sp.

3_4_o_b _ / ___ CH30- H H CH3 H 227-229

Cl H H CF3 H 161-162 F H H F H 210-212

Br H H Br H 201-204 CH30- H H ch3 ° - H 198-199 CH H H Br H 170-172

Cl H H NO 2 H 225-228

Cl HH CHgO- H 180-181 C3H? 0- HH C3H7 ° H 188-189 nC H O- HH nC ^ HgO- H 165-167 CH O- HHCH O- H 181-183 lolo CHgO- HHFH 192-194 CH30 - HH Cl H 197-198

Cl H H Cl H 189-190 CHg H H Cl H 181-183

Cl HH CHg H 216-217 CHg HH NOg H 205-207 CHg HH -CH (CH3) 2 H 110-116 CH HH CHg H 187-189 CHgO- H CHgO- HH 173-175 CHgO HHHH 193-195 CHgO H Cl CHgO H 141-143 CHg Cl H Cl H 186-189 (CHg) 2CH HH (CHg) 2CH H 161-163 CHgS HHHH 211-214 HH CHgO NOg H 210-212

Cl H H H CHg 171-174 CHg H CHg H CHg 197-198 F H F H F 219-221

Cl H Cl H Cl 194-195 CHgO- H CHgO- H CHgO- 180-181

Cl Cl H Cl Cl 223-2 24 CHg CHg H CHg CHg 182 ~ 184 CFg H H H H 219-220 CHgO Cl H Cl H 183-185 CHg Cl H NOg H 207-209 CH3 CH3 H NOg H 225-227 70577 20

Table I-D

°; <c ”3 r5 - (_) _ so2ncnh - /)> - \ H N ~ \

R "R XX

4 3 R3 R4 R5 r6 r7 X sp.

H H H H H H 187-189 CH3 H H H H -CII2OCH3 15 7-138

Cl H H H H -CH., 0CHo 179-18 !;

2 O

Cl H H Cl H -CH.OCII 174-176 CHo0- H H CH 0- H -CH „0CHQ 155-157 5 3 i 3 F H H H H H 192-193 CH3 H H H H H 211-213

Cl H H H H H 2 01-2 03 H Cl H H H H 198-199 F Cl H H H H 219-220 CH3 Cl H H H H 211-213 F H Cl H H H 222 - 235 (d) H Cl H Cl H H 201-203 CH30- H H Cl H H 224-226

Cl H H Cl H H 207-209 CH3 H H Cl H H 217-219 F H H F H H 173-199

Cl H H H Cl H 160-163 H H H H H C0Hc 0-180-182 l b CH3 H H Cli3 H C2H5 ° - 130-134 H H H H H (CH3) 2CHO- 116-120 H H H H H Cl. 213-215 H Cl H H H Cl 194-195 H H H H H CH3S- 208 (d) K H H H H -CF3 179-182 CH 3 H H II H -CF.j 172-174

Cl H H H H -CFQ 17 3-17 5 21 70577 R3 K4 RS R6 R7 X Sp 'H H H -CF3 H -CF3 160-163 NO2 H H H H Cl 17 0-17 2

Table I-E

/ R7 0CH3 6 \ .- /> 0 N - <d r -Γ> —SO.NHCNH-Γ x> 5 W 2 \ n ^ / T R3 R0 R ,, Rc Rc R ^ X m.p.

o 4 o b / H H H H H H 199-200 (d) H H H H H Cl 181-183

Cl H H H H Cl 185-188 CH3 H H H H Cl 176-178

Cl H H Cl H Cl 20 2-2 05 H H H H H CH ^ S- 199-196

Cl H H H H CH3S "195-199 H H H H H -CF3 164-168

Cl H H H H -CF 3 204-208 CH 3 H H H H -CF 3 171-173 H H H -CF 3 H -CF 3 191-194 H H H H H C 2 H 5 ° "163-165

Cl H H H H C „Hr0- 142-144 2 5 CH, H H H H C„ Ht 0- 148-149

o ZD

22 70577

Example 3 NZ.T (4,6-dimethyl-pyrimidin-2-yl) -amino] -fonyl] -2-thiophenesulfonamide To 12 g of 2-amino-4,6-dimethyl-pyrimidine 2 in 50 ml of acetonitrile was added with stirring. g of 2-thiophenesulfonyl isocyanate.

The resulting mixture was stirred for 2 hours and filtered to give the desired solid product, m.p. 211-216 °. The infrared spectrum for this product -1 -1 L gave absorption peaks at 1540 cm, 1605 cm and 1700 cm.

Example 4 N-yl (2,6-dimethylpyrimidin-2-yl) aminocarbonyl-2,5-dichloro-3-thiophenesulfonamide

To a suspension of 12 g of 2-amino-4,6-dimethylpyrimidine in 300 ml of methylene chloride was added 26 g of 2,5-dichloro-3-thiophenesulfonyl isocyanate at ambient temperature. 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 gave -1 -1 L of infrared absorption peaks at 1550 cm, 16G5 cm and 1690 cm. Example 5 N - [(4-methoxy-6-methylpyrimidin-2-yl) aminocarbonyl] -2-furansulfonamide

To a solution of 2.10 g of 2-furansulfonyl isocyanate UC in ml of methylene chloride was added 1.60 g of 2-amino-4-methoxy-6-methylpyrimidine. The resulting mixture was stirred for 1 hour at room temperature, then heated to reflux for 15 minutes and the solvent removed in vacuo. The resulting solid was allowed to stand in ethyl ether containing a small amount of acetonitrile for one day and then filtered and dried to give the desired product, melting at 185-188 ° (dec). Using an equivalent amount of the appropriate 2-aminopyrimidine and an appropriately substituted thiophene or furansulfonyl isocyanate, the following compounds of Table II can be prepared by the method of Examples 3-5:

II

23 7 0 5 7 7

Table II-A

0 N X

ft% S0.NHC-NH / 7 X \ ___,

(N7 2 W

Rg Q X Z m.p.

H S CHg CHgO- 207-208 H S CH3 ° - ch3 ° - 206-2 07

Cl S CHg CH30- 186-187

Cl S CH3 CHg 198-199

Cl S H CHg 197-198 CHg S CHg CHg 0- 132-144 CHg S CHg 0- CH g ° - 159-169 H 0 CHg CHg 0 185-188

Table II-B

° / "x / X SOjNHCNhV ') - H

Γ \ N "\ z V" R10

Rg R10 X z sp '

Cl Cl CHg CHgO- 186-188

Cl Cl CHg ° - CHgO- 201-202

Br Br CHg CHg 188-195 2 * 70577

Example 6 (6-Dimethylpyrimidin-2-yl) amine carbonyl] -1-naphthalenesulfonamide

To a suspension of Ib, 6 g of 2-amino-4,6-dimethoxypyrimidine in 4 ml of acetonitrile was added with stirring 23.3 g of 1-naphthalenesulfonyl isocyanate. After stirring for 14 hours, the desired solid was removed by filtration and, after washing with a small amount of ethyl ether, melted at 177-178 ° C.

Using an equivalent amount of the appropriate 2-aminopyrimidine and 1-naphthalenesulfonyl isocyanate, the following compounds of formula I can be prepared by the method of Example 6: N- (4- (4-chloro-6-methylpyrimidin-2-yl) aminocarbonyl). naphthalenesulfonamide, m.p. 235-207 ° N - [(4,6-dimethylpyrimidin-2-yl) aminocarbonyl] -1-naphthalenesulfonamide, m.p. 201-202 ° N-yl-4-methylpyrimidin-2-yl) aminocarbonyl (1-7-1-naphthalenesulfone i-amide, m.p. 132-183 ° N- (4-methoxy-6-methylpyrimidin-2-yl) aminocarbonyl-1-naphthalenesulfonamide, m.p. 210-211 °

Example 7 N-IS 3 (6-dimethylpyrimidin-2-yl) aminothioxomethyl (benzenesulfonamide)

To a dry suspension of 12.4 g of 2-amino-4,6-dimethylpyrimidine in 3 ml of acetonitrile was added 19.9 g of benzenesulfonyl isothiocyanate. The resulting heavy precipitate was removed by filtration and washed with anhydrous ethyl ether. It melted at 165-1 / 0. The product was N- (S (4,6-dimethylpyrimidin-2-yl) amino-dioxomethyl) benzene is an amide.

Using an equivalent amount of the appropriate sulfonyl isothiocyanate and appropriately substituted aminopyrimidine, the compounds of Table III can be prepared by the method of Example 7: 2s 70577

Table III-A

Rfi D o Λ N-Λ N -rf 'R ^ / ^) - SO2NHC-Mi </ _ \ R0 R Rc Rc R-, X Z sp.

H H H H H CH3 cH30- 188-189 H H H H H CH30 CH30 192-193

Cl H H H H CH3 ch3 ° - 184-185

Cl HHHH CH3 ° “CH30- 169-172 CH3 HHHH CH3 CH30 165-167 CH3 HHHH CH3 ° - CH30- 181-182 CH30- HH ch3 0- H CH3 CH30- 178-180 CH30- HH CH30 - H CH30- ch3 ° - 191-193

Table IIT-B

/ M \ "/ Λ

Rg X Z m.p.

H CH3 ch3 ° - 196-197 H CH3 ° - ch3 ° - 202-204 CH3 CH3 ch3 C- 132-144 CH3 CH3O_CH3 ° "159-169 26 70577

Example. 8 2-Furanisulfonyl isocyanate // v. NBuLi _____ \ // \\ h 'h \ 0 / Et 2 O, RT' -o ^ Li '3 ° V-O / XS02Li

Excess (COCl) 2 ^ Ce, _ ^ lf ~ i NH ^ OH jj \

Ho0, HC1X, \ 0-5 ^ Λ - \ 2 o so2ci 0 so2nh2 r \ Ό '^ SO2NC0 A. Lithium 2-furan sulfinate

To a solution of 39.6 g of furan (585 mL) in 200 mL of anhydrous ethyl ether was carefully added 100 mL of 1.6 M n-butyl in hexane under a nitrogen atmosphere while maintaining the reaction temperature at 30 or below. The mixture was stirred until precipitation appeared complete. After cooling to -25-30 °, gaseous sulfur dioxide was slowly passed through the mixture for two hours. The mixture was stirred at room temperature for an additional 90 minutes and the precipitated lithium 2-furansulfinate was filtered and washed with acetone. Sp. 250 °. Infrared spectrum IR (Nujol) 3100-3000 cm -1 (W), 1700 cm -1, 1550 cm -1 (VW), 1210 cm -1, 1110 cm -1, 1115 cm -1 (m), 1020 cm -1 (VS), 91 fJ cm -1, 880 cm -1, 8 25 cm -1 (W), 7 3 5 cm -1 (S).

? 7 70577 13. 7-Furan is u 1 f onyl 11 chloride 90 ml of water, 410 ml of concentrated HCl and 6 8.0 g of 1N-thiuron-2-furan sulfinate were mechanically stirred and cooled to 10-15 ° . Liquid chlorine (12.3 mL, 39.4 g) was added dropwise over 30 minutes. The mixture was stirred for a further 30 minutes at 5 ° C, poured onto ice and extracted with methylene chloride. Evaporation of methylene chloride gave 44 g of 2-furan sulfonyl chloride, bp 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-Furanesulfonamides 23 g of 2-furansulfonyl chloride (138 mL) were added dropwise to 200 mL of concentrated NH 4 OH at 0-5 °. After stirring overnight at room temperature, the water was removed in vacuo and the precipitate was washed with ice water and dried. Yield 14 g of 2-furansulfonamide, m.p. 120-122 °. (Literature mp 120-122 °: JOC 18, 894 (1953)). IR (Nujol) 3250 cm -1, 3100 cm -1, 1600 cm -1 (W), 1550 cm -1, 3190 cm -1, 1140 cm -1, 1120 cm -1, 1055 cm -1, 1005 cm -1, 930 cm 1, 880 cm -1, 843 cm -1 (S).

D. 2-Furanesulfonyl isocyanate i

Dry toluene (150 mL), 25 mL of oxalyl chloride (295 mL) and a small amount of DABCO (diazabicyclo / 2.2.2 octane) were heated to 90 °. 10 g of 2-furansulfonamide were added over 15 minutes and the mixture was kept at 95 ° for 2 hours. After filtration, the solvent was removed in vacuo to give 2.1 g of an oil which gave a characteristic isocyanate absorption in the infrared spectrum (2280 cm 1).

Example 9 N - ((9,6-dimethyl-1,3,5-triazin-2-yl) aminocarbonyl) -2-methylbenzenesulfonamide to 12.3 g of 2-amino-4,6-dimethyl-1,3, 5-Triazine in 250 ml of dry acetonitrile was added with stirring 19.7 g of 2-methylbenzenesulfonyl isocyanate 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 product obtained, N - (4,6-dimethyl-1,3,5-triazin-2-yl) aminocarbonyl-7-2-methyl] benzenesulfonamide, melted at 141-145 ° C.

? 8 70577

Example 10 N-Z '(4,6-Dimethyl-1,3,5-triazin-2-yl) aminocarbonyl) -7-2-chlorobenzenesulfonamide to 12.3 g of 2-amino-4,6-dimethyl -1,3,5-Triazine In 200 ml of triethyl of acetone was added with stirring 21.7 g of 2-chlorobenzenesulfonyl isocyanate. All solids dissolved after the reactants were added and the mixture was evaporated to dryness. The solid residue was triturated with ethyl ether and isolated by filtration to give crude N - [(4,6-dimethyl-1,3,5-triazin-2-yl) aminocarbonyl] -2-chlorobenzenesulfonamide, m.p. 115-118 The nuclear magnetic resonance absorption spectrum of this product in trifluoroacetic acid had singlet peaks of 2.59 and 2.9 ppm.

Example 11 N - [(4,6-dimethoxy-1,3,5-triazin-2-yl) aminocarbonyl] -2-chlorobenzenesulfonamide to 15.6 g of 2-amino-4,6-dimethoxy-1, To 3,5-triazine and 300 ml of dry methylene chloride containing 0.1 g of 1,4-diazabicyclo [2.2.2] octane were added 21 g of 2-chlorobenzene isulfonyl isocyanate with stirring. The solid formed after washing the solid with 1-chlorobutane, N - [(4,6-dimethoxy-1,3,5-triazin-2-yl) -aminocarbonyl] -2-chloro-benzenesulfonamide, melted 188- 189 ° C. Infrared absorpto analysis gave absorption peaks at 1740 cm, 1630 cm-1 and 1595 cm-2, which are typical of these types of compounds.

Using the procedure of Examples 9-11 with an equivalent amount of the appropriate aminotriazine and appropriately substituted sulfonyl isocyanate, the compounds shown in Table IV can be prepared: 29 70577

Table IV-A

<V ^ -SO2NHCNH- ^ N

<z X_Z_sp.

CH3 CH3 200-201 CH30 CH30 183-185 CH30 CH3 166-171 CH3CH2CH2O CH30 121-124 CH3S CH30 197-199

Table IV-B

X

QO N— ^

SO ,, NH-C-NH - \ N

r2

R3 X z m.p.

CH3 CH30 CH3 158-162 CH3 CH30 CH30 144-147 CH3 CH3OCH2 CH3 147-150 CH3 CH3S CH30 191-193

Cl CH3 CH3 185-187

Cl CH30 CH3 174-178

Cl CH30 CH30 188-189

Cl CH3OCH3 CH3 142-145

Cl CH3CH2O CH3 117-121

Cl CH3CH2O CH30 132-133 F CH30 CH3 168-172 30 70577

X z sp. ° C

F CH30 CH30 169-175 CF3 CH3 CH3 172-174 CF3 CH3 CH30 165-167 CF3 CH30 CH30 171-173 NO2 CH3 CH30 178-181 (dec.) NO2 CH30 CH30 175-178

Cl CH3S CH3 160-175

Cl Cl CH3 180-182

Br CH3 CH3 194-196

Br CH 3 CH 3 O 180-181

Br CH30 CH30 175-176 F CH3CH2O CH3 168-170 no2 ch3 ch3 105-110 CH3S CH30 CH3 181-184 CH3S CH30 CH30 171-174 CH30 CH3 CH3 193-195 CH30 CH30 CH3 175-179 CH30 CH30 CH30 163-165 C Hr CH0 CH „152-157 C2H5 CH30 CH3 127-132 C2H5 CH30 CH30 152-157 nC ^ Hg CH3 CH3 159-162 n-C3H7 CHgO CHgO 149-153 CN CHgO CHgO 130 31 70577

Table iy-C </ SCkNHCNH ^ n W \ -ς

Rg X Z m.p.

Cl CH3 CH3 190-191

Cl CH3 CHgO over 250 CF3 CH3 CH3 158-162 CHg CH3 CH3 184, re-solidifies CHg CHgO CHgQ 174, re-solidifies

Table IV-D

, -. IS

/ Qy ~ S02NHCNH \

R4 R3 Z

R3 R ^ X Z m.p.

Cl Cl CH3 CH3 130-140

Cl Cl CH3 CH30 182-184

Cl Cl CHgO CH30 192-193 F Cl CH3 CH3 171-175 F Cl CH3 CH30 190-191 F Cl CH30 CH30 275

Cl CH3 CH3 CH3 188-189

Cl CH3 CH3 CH30 187 R3 R4 X Z m.p.

32 70577

Cl CH3 CH30 CH30 148-151 CH30 Cl CH30 CH30 178 CH30 Cl CH3 CH30 172-174

Table iy-E

/ -Γ \ H N Rc - (() VSO 0 NHCNH - (\ N

b \ ^ / z N J

R3 ^ R3 R5 X Z m.p.

Cl Cl CH30 CH30 182-190 F F CH30 CH30 196-200 CH3 CH30 CH3 CH30 155-156 CH30 CH30 CH30 CH30 218-219 NO2 Cl CH30 CH3 163-164

Table IV-F

RKy s j S 0 2 NH CHNf {

\ 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 CH3CH2O CH3 155-159

Cl Cl CH3CH2O CH30 147-149

Cl CN CH3 CH30 190-193 R3 Rg X Z m.p.

70577 33 CH3 CH3 CH3 CHgO 160-163 CH3 CH3 CH30 CH30 169-173 CH30 Cl CH3 CHgO 174-179 CH30 Cl CH30 CH30 165 CHgO Cl CH3CH20 CH3 183-183.5 CH30 F CH30 CH30 201-203 FF CH3 CH3 164-165 FF CHgO CH30 206-208

Cl CH30 CH3 CH30 176 ci ch3o ch3o ch3o 201

Cl CF3 CH3 CH2O 177-178

Cl CF3 CH30 CH30 165-167

Cl H CHgO CH3 110-112 ClgCOCT salt

Cl H CH 3 O 3 CH 3 oil (CH 3 CH 2 CH 2 CH 2) 4 N + salt

Cl H CH 3 O 3 CH 3 oil ε CH 3 (CH 2) 674N + salt

Cl NO 2 CH 3 CH 3 142-144

Cl NO2 CH30 CH30 168-174 CH30 CH3 CH30 CH30 210-213 F CH3 CH3 CH3 180-182 F CH3 CH3 CHgO 185-186 F CH3 CH30 CHgO 191-192 CH3 F CH3 CH3 201-205 CH3 F CH30 CH30 183-184 CH3 CH 3 SO 2 CH 3 CH 3 181-184 (d) CH 3 S Cl CH 3 CH 3 O 95-100 CH 3 S Cl CH 3 CH 3 O 190-194 CH 3 NO 2 CH 3 CH 2 O 190-191 CH 3 NO 2 CH 3 CH 2 O 190-230 (dec.) Na salt 34 R 3 Kg XZ m.p.

70577 CH3 NO2 CH30 CH30 142-145 CH3 (CH3) 2CH CH3 CH3 167 ch3 cch3) 2ch ch3 ch3o 115 CH3 (CH3) 2CH CH30 CH30 135 CH3CH2O Cl CH3 CH30 179-181 CH3CH20 CH3CH2O3 CH3 CH3 134-136 CH, CH _ 0 CH, CH „0 CH, 0 CHo0 187-188 CH3 Cl CH3 CH3 189-191 CH3 Cl CH3 CH30 172-174 CH, Cl CH, 0 CH 0 182-184

ό ό O

Br Br CH3 CH2 204-205

Br Br CH 3 CH 2 O 178-180

Br Br CH30 CHgO over 275 CH30 CH30 CH3 CH3 144-150 CH30 CH30 CH3 CH30 187-205 (dec.) CH30 CH30 CH3 CH30 oil (CH3CH2CH CH2) ^ Ν + - salt CH30 CH, 0 CH30 CH30 187-188 CH30 CH30 CH3CH2O CH3 96-100 CH30 CH30 CH3CH2O CH30 138-141 (CH3) 2CH (CH3) 2CH CH30 CH30 123-128 CH3CH2O Cl CH30 CH30 174-178 35 70577

Table IV-G

/ - / 7 0 N

(Cj) -SO0NHCNH ~ \ N \ ^ / 2 R3 R3 R7 X Z m.p.

Cl Cl CH3 CH3 142-158

Cl Cl CH3 CH30 203-206

Cl Cl CH30 CH30 205-208

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 CHgO CH30 275

Cl CH30 CH30 CH30 174-178

Table IV-H 6) - \ 2 N

/ QVS02nh ^ nh N

> _ / N = <

r4 Z

R4 R6 X Z m.p.

Cl Cl CH3 CH3 210-213

Cl Cl CH30 CH30 207 3 6 70577

Table XV "1 / ΤλΥ A / N = ^ RS- <O / 302NHCNH- <n ^ R4 z K4 R5 X Z m.p.

Cl Cl CH3 CH3 194-195

Cl Cl CH3 CH30 188-190

Cl Cl CH30 CH30 280 NO2 CH30 CH3 CH30 182-185

Table IV-J 0

R 2 VfYV 5 O 2 NHCNH -4 N

Ί R3 R3 R4 R5 X z sp.

Cl Cl Cl CH3 CH3 178-184

Cl Cl Cl CH3 CH30 169-171

Cl Cl Cl CH30 CH30 175-178 37 70577

Table IV-K

/ P ^ V-SO NHCNH -ζ \ R3 r3 \ rg X Z sp.

CH, CH3 NO2 CH3 CH30 182-1314 (dec.) CH CH NO2 CH3 CH3 196-197 (dec.)

Table IV-L

/ - \ 7 0 Ν ^ Χ <Oso2NHCNH - (v ^

R44 'R3 Z

r3 r4 r7 X Z sp.

CH3 Cl Cl CH3 CH3 168-170 CH3 Cl Cl CH30 CH3 176-178 CH30 Cl Cl CH30 CH30 173-175

Table IV-M

«/ N ^

R. - (()) - SO, NHCNH N

5 urv 2 'n R3 ^ R3 R, Rg X Z m.p.

Cl Cl Cl CH3 CH3 184-186

Cl Cl Cl CH3 CH30 169-171

Cl Cl Cl CH30 CH30 165-168 CH30 Cl CH30 CH30 CH30 195 38 70577

Table IV-N R X

Rr- (O VsO 2 NHCNH-L N

5uk (2 Λ Λ, R3 z

Rg Rg Ry X Z sp.

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 CH30 152-155 F F F CH30 CH30 194-196

Cl Cl Cl CH3 CH3 188-190

Cl Cl Cl CH3 CH O 159-161

Cl Cl Cl CH30 CH30 166-168

Table IV-0 Rg \ / ^ 7 O j \ j <Q> -so2nhcnh ^)

K * 3 Z

R3 R4 4 Rg Ry X Z m.p.

CHg CHg CH3 CH3 CH3 CH3 200-205 CH3 CH3 CHg CHg CHg CHgO 195-197 CH3 CH3 CHg CH3 CHgO CHgO 185-189

Cl Cl Cl Cl CHg CHgO 187

Cl Cl Cl Cl CH30 CHgO over 250 39 70577

Example 12 4-Methoxy-6-methyl-1,3,5-triazin-2-yl) aminocarbonyl-117-2-thiophenesulfonamide

To a suspension of 14.0 g of 2-amino-4-methoxy-6-methyl-1,3,5-triazine in 300 ml of acetonitrile was added dropwise 19 g of thiophene-2-sulfonyl isocyanate. After stirring for 6 hours, the mixture was filtered to give the desired solid product, melting at 182-184 ° C.

Using the method of Example 12 in equivalents with amounts of the appropriate amino-1,3,5-triazine derivatives and sulfonyl isocyanate, the compounds of Table V can be prepared.

Table V-A

S

--tSO 0 NH-C-NH-χ N

I il 2 'n - = <^ 8Λθ

Rg R10 X Z sp * C1 Cl CH3 CH3 127-133 C1 Cl CH3 CH30 165-171 C1 Cl CHgO CHgO 181-184

Table V-B

Oso2jnh7 t R8 V \ ^ E X z Q sp.

a8 H CH3 CH3 s 174-176 H CH3 CHgO S 182-184 H CHgO CHgO S 191-192 CH CH3 CHgO S 159-162 4 0 70577

Rg X Z Q sp.

Cl CHg CH3 S 192-195

Cl CHg 0 CH30 S 193-195 H CH3CH2 CH3 S 132-138 H CH ^ S CH0 S 223-225 ö 3

Example 13 N-ZK 4,6-dimethoxy-1,3,5-triazin-2-yl) aminocarbonyl-1-naphthalenesulfonamide

To a stirred suspension of 16 g of 2-amino-4,6-dimethoxy-1,3,5-triazine in 400 ml of acetonitrile was added dropwise 23.3 g of 1-naphthalenesulfonyl isocyanate. The mixture was stirred for 14 hours and the resulting solid product was removed by filtration.

After washing with ethyl ether, the product melted at 171-172 ° C.

Using the procedure of Example 13 and substituting equivalent amounts of the appropriate Amine 1,3,5-triazine and sulfonyl isocyanate, the following compounds of Table VI can be prepared:

Table VI

0 n K /

S0, .NHCNH “V N

K

X Z sp.

CH3 CH3 179-183 CH3 CHg0 186-188 CHgO CHgO 171-172

Example 14 N- (4,6-Dimethoxy-1,3,5-triazin-2-yl) aminothioxomethyl-7-benzenesulfonamide

A mixture of 20 g of benzenesulfonyl isothiocyanate, 15.6 g of 2-amino-4,6-dimethoxy-1,3,5-thiazine, 250 ml of acetonitrile and a catalytic amount of dibutyltin dilaurate was stirred for 24 hours. After filtration to remove unreacted triazine, a rubbery residue was obtained by evaporation of acetonitrile.

70577 41

Trituration of this material with ethyl ether precipitated the desired compound, which was isolated by filtration and melted at 148-150 ° C.

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.

Table VII

r1so2nh? NHR 2

Ra R2 Sp 'CN «9CHo gas at <118 ° C, m.p.

\ - / N ^ 2 5 0 ΧΗ3 JT \ \ Γ /, N Λ 182-185 H -f * N _ / ch ^ och3 (> - _3 142-144 ^ “4 / * CHo0 v N _ /) Τ \ ~ ^ ch3 <7 7- N ~ d0CH, \ _ / Λ 188-190 (dec.)

Vh, Λ / N

3 N = / ^ CH3

formulations

Useful formulations of the compounds of formula I may be prepared in a conventional manner. They include dusts, granules, pills, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates, etc. Several of these can be used directly. The formulations to be sprayed can be diluted in a suitable medium and used in spray volumes from a few liters to many hundreds of liters per hectare. Very strong combinations are used primarily as intermediates for further formation.

4 2 70577

The formulations generally contain about 0.1 to 99% by weight of active ingredient (s) and at least one of the following: a) about 0.1-20% of surfactant (s) and b) about 1-99.9% by weight. % solid or liquid extender (s). In particular, they contain these ingredients in the following approximate proportions: 4 3 70577 e

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μ c o in o tn

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lp (Ti, 1 till

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cl, rd a) ^ c ^ _ • H μ -zf- m -zt o> o \ o

ifl a) t— ΟΛ dj CX \ θ '»H

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mc o o o o m o μ -h -M- -zt c- <d td H ^ c

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n c oo characteristic m -Htt n in mcMChOv j

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n '1 2 o m o h h o 5 μ c H o M M -H ~ 3 <td td

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id 3 h μ> μ

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μ rH

CD c co id x id ο λ; 3 3 h 6 μ rH: td μ 6

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Of course, the active ingredient may be present in both smaller and larger amounts depending on the intended use and the physical properties of the compound. Higher ratios of surfactant to active ingredient are sometimes desired and can be achieved by combining the formulation or by mixing in a container.

Typical solid extenders are described in Watkins et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Edition, Dorland Books. Caldwell, New Jersey. More absorbent extenders are preferred for wettable powders and tighter for dusts. Typical liquid diluents and solvents are described by Marsden in "Sovents Guide", 2nd Edition, Interscience, New York, 1950, A solubility of less than 0.1% is preferred for suspension concentrates; The solution concentrates are preferably resistant to phase separation at 0 ° C. McCutcheon's Detergents and Emulsidiers Annual, Mc Publishing Corp., Ridgewood, New Jersey, and Sisely and Wood's Encyclopedia of Surface Active Agents, Chemical Publishing Co., Inc., New York 1964, list surface active substances and recommended uses. All formulations may> contain small amounts of additives to reduce foam, agglomeration, corrosion, microbiological growth, etc.

Methods for preparing such combinations are well known. Solutions are prepared simply by mixing the ingredients. Fine solid combinations are made by mixing and usually grinding, such as in a hammer mill or liquid energy mill. Suspensions are prepared by wet milling (see, e.g., Littler, U.S. Patent 3,060,084). *

Granules and pills can be made by spraying the active ingredient onto preformed granular carriers or by agglomeration methods. See. JE Browning, Agglomeration, Chemical Engineering,; December 4, 1967, pp. 147-, and "Perry's Chemical Engineer's Handbook,"; 4th edition, McGraw-Hill, New York, 1963, pp. 8-59. j

For more information on the type of formulation, see, for example: H.M. Loux, U.S.A. Patent 3,235,361, February 15, 1966, column 6, line 16 to column 7, line 19, and Examples 10-41.

R. W. Luckenbaugh, U.S.A. Patent 3,309,192, March 14, 1967, from column 5, line 43 to column 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182.

i l {^ 70577 H. Gysin and K. Knusli. , U.3. pat ent L i 2. 89 1,855, 2 June 3, 1959, from row 3 of column 66 to row 17 of column 5, and Examples 1-4.

G.C. Klingman, "Weed Control as a Science", John Viley &

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 indicated.

Example 15 Wettable powder N-Z (4,6-dimethylpyrimidin-2-yl) aminocarbonyl-7-benzenesulfonamide 80% sodium alkylnaphthalenesulfonate 2% sodium lignin sulfonate 2% synthetic amorphous silica 3% kaolinite 13%

All ingredients are mixed, ground in a hammer mill until all solids are substantially less than 50 microns in size, and then mixed again.

Example 16 Wetting powder NZ ”(4-ethoxy-6-methylpyrimidin-2-yl) aminocarbonyl] -2-chloro-5-methoxybenzene sulfonamide 50% sodium alkylnaphthalenesulfonate 2% low viscosity methylcellulose 2% milk 46%

The ingredients are mixed, coarsely ground in a hammer mill and then in an air mill to give active particles substantially less than 10 microns in diameter. The product is mixed again before packaging.

Example 17 Granules

Example 16 wettable powder 5% attapulgite granules 95% (U.S.S sieve size 20-40 mesh; 0.84-0.42 mm)

A wettable powder slurry containing about 25% dry matter is sprayed onto the surface of the attapulgite granules in a twin cone mixer. The granules are dried and packaged.

τ 70577

Example 18

Oral suppository pill N-Z "(4-methoxy-6-methylpyrimidin-2-yl) aminocarbonyl] -2-chlorobenzenesulfonamide 25% anhydrous sodium sulfate 10% crude calcium lignin sulfonate 5 L sodium alkylnaphthalene sulfonate

The ingredients are mixed, ground in a hammer mill and then moistened with about 12% water. The mixture is extruded into cylinders about 3 mm in diameter, which are cut to give pills about 3 mm long. These can be used directly after drying or the dried pills can be muscled to pass U.S.A. Well. 20 sieve (openings 0.84 mm). Granules that remain in U.S.A. Well. 40 sieves (openings 0.42 mm) are packaged for use and the finer ones are returned. Example 19 01suspension N-Z- (4,6-dimethoxypyrimidin-2-yl) aminocarbonyl] -2,5-dichlorobenzenesulfonamide 25% polyoxyethylene sorbitol hexoleate 5% highly aliphatic hydrocarbon oil 70%

The ingredients are ground in one sand mill until the diameter of the solid particles has decreased to less than about 5 microns. The resulting suspension can be used directly, but preferably after dilution with oils or. it is emulsified in water.

Example 20 Wettable Powder N - C (4,6-Dimethylpyrimidin-2-yl) amino-carbonyl] -2,5-dichlorobenzenesulfonamide 20% Sodium Alkylnaphthalenesulfonate 4% Sodium Lignin Sulfonate 4% Low Viscosity Methylcellulose 3% attapulgitis 69%

The ingredients are mixed thoroughly. After grinding in a hammer mill to obtain particles substantially all less than 100 microns in diameter, the material is remixed and v / 70577 and screened by U.S.S. Well. Through a 50 sieve (aperture 0.3 mm) and packed. Example 2 1

Low concentration granules N- (X (4-methoxy-6-methylpyrimidin-2-yl) aminocarbonyl) -2-methylbenzenesulfonamide 1% N, N-dimethylformamide 9 o attapulgi i tt i-granule .ita 90% (USS screen size 20-40 mesh).

The active ingredient is dissolved in a solvent and the solution is sprayed onto the dedusted granules in a twin cone mixer. After the injection of the solution is completed, the stirrer is allowed to run for a short time and then the granules are packed.

Example 22 Aqueous suspension of N-ZT (4,6-dimethylpuridin-2-yl) aminocarbonyl-7-benzenesulfonamide 40% polyacrylic acid thickener 0.3%

dodecyl phenol polyethylene glycol ether a 0.5 E

disodium phosphate 1.0% monosodium phosphate 0.5% polyvinyl alcohol 1.0% water 56.7%

Ingredients; mixed and ground in one sand mill to give particles that are essentially all through less than 5 microns in size.

Example 23 Solution of the sodium salt of N-Z- (4-methoxy-6-methylpyrimidin-2-yl) aminocarbonyl] -2-chlorobenzenesulfonamide 5% water 95%

The salt is added directly to the water with stirring to give a solution which can then be packaged for use.

Example 24

Low concentration granules N- [7 (4,6-dimethylpyrimidin-2-yl) aminocarbonyl] -10.1% 2,6-dichlorobenzenesulfonamide and attapulgite granules (USS 20-40 mesh) 99.9% .s 70577

The active ingredient is dissolved in a solvent and the solution is sprayed onto the dedusted granules in a twin cone mixer. When the injection of the solution is completed, the substance is heated to evaporate the solvent. The substance is allowed to cool and then packaged.

Example 25 Retrieves N-Z '(14,6-dimethoxypyrimidin-2-yl) aminocarbonyl] -2,5-dichlorobenzenesulfonamide 80%

Moisturizer 1% crude lignin sulphonate salt (contains 5-20 o-natural sugars) 10% attapulgite clay 9%

The ingredients are mixed and ground to pass through a 100 mesh screen. This material is then added to the fluidized bed granulator, the air stream is carefully set to fluidize the material, and a fine jet of water is sprayed onto the fluidized material. Fluidization and spraying are continued until granules of the desired size are obtained. The spraying is stopped but the fluidization is continued, optionally using heat until the water content has dropped to the desired level, usually below 1%. The material is then removed from the device, screened to the desired diameter range, usually 14-100 mesh (1410-149 microns), and packaged for use.

Example 2G

Very strong concentrate N - [i 4,6-dimethyl. 1-pyrimidin-2-yl] aminocarbonyl-2-ticphenenesulfonamide 99% silica airgel 0.5% synthetic amorphous silica 0.5%

The ingredients are mixed and ground in a hammer mill to give a material that is substantially all permeable to U.S.A. no 50 sieve (0.3 mm aperture). Concentrate can be further formed if necessary.

Example 27 Wettable Powder: NZ ”(4-methoxy-6-methylpyrimidin-2-yl) aminocarbonyl] -2-chlorobenzenesulfonamide 95% dioctyl sodium sulfosuccinate 0.1% synthetic fine silica 4, 9%

II

49 70577

The ingredients are mixed and ground in a hammer mill to give particles, all of which are substantially less than 100 microns in diameter. The substance is screened in U.S.A. Well. Through a 50 sieve and packed. Example 28 Wettable powder: N-ZT (4,6-dimethoxy-pyrimidin-2-yl) -aminocarbonyl] -2,5-dichloro-benzenesulfonamide MO% 2,5-Dichloro-benzenesulfonamide amide sodium lignin sulfonate 20% montmorillonite clay 40%

The ingredients are mixed thoroughly, coarsely ground in a hammer mill and then in an air mill to give particles substantially all less than 10 microns in size. The substance is remixed and packaged.

Example 29 01.suspension o NZ "(M-methoxy-6-methylpyrimidin-2-yl) -31) aminocarbonyl17-2-methylbenzenesulfonamide dust dust mixture 1 carbonic acid A mixture of acid barriers and oil-soluble petroleum sulfonates in xylene 59%

The ingredients are combined and ground together in a sand mill to give particles, the kicks are basically all less than 5 microns in size. The product can be used directly, diluted with oils or emulsified in water.

Example 30 Wettable powder N - [(M, 6-dimethoxy-1,3,5-triazin-2-yl) aminocarbonyl] benzenesulfonamide 80% sodium alkylnaphthalenesulfonate 2% sodium lignin sulfonate 2% synthetic amorphous silica 3 L , Kao 1 in ii (. ti α 1 3 7

The ingredients, mixed, are ground in a hammer mill until the solids size is substantially less than 50 microns, remixed and packaged.

so 70577

Example 31 Wettable Powder N - [(4,6-dimethyl-1,3,5-triazin-2-yl) amino] carbonyl / benzenesulfonamide 50% sodium alkylnaphthalenesulfonate 2% low viscosity methyl cellulose 2% silicate 96%

The ingredients are mixed, coarsely ground in a hammer mill and then in an air mill to give particles, essentially all of which are less than 10 microns in diameter. The product is remixed before packaging.

Example 32 Granules

Example 31 wettable powder 5% attapulgite granules 95% (U.S.S. screen number 20-90 mesh; 0.84-0.92 mm)

A wettable powder slurry containing about 25% dry matter is sprayed onto the surface of the attapulgite granules in a double cone mixer. The granules are dried and packaged.

Example 33

Extruded pill: N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) aminocarbonyl] -2-chlorobenzenesulfonamide 25% anhydrous sodium sulfate 10% crude calcium lignin sulfonate 5% sodium alkylnaphthalene sulfonate sulfonate sulfonate sulfonate sulfonate 59%

The ingredients are mixed, ground in a hammer mill and then moistened with about 12% water. The mixture is extruded with a diameter of approx.

Into 3 mm cylinders cut to give pills about 3 mm long. These can be used directly after drying or the dried pellets can be crushed to pass the U.S.S. sieve (0.84 mm apertures). Granules that remain U.S.S. Well. A 40-mesh screen (0.42 mm openings) can be packed for use and the fins returned.

51 70577

Example 35 Oil suspension N-Z- (4,6-climethoxy-1,3,5-tridazin-2-yl) amino-3 3% carbonyl-7-chloro-5-methoxybenzenesulfon -amycl and polyoctylene sorbitol hexaoleate 5% very aiiiau11is La hii 1 i ve Beat 70%

The ingredients are ground in one sand mill until the diameter of the solid particles has decreased to less than n, 5 microns. The resulting suspension can be used directly, but preferably after being diluted with oil or emulsified in water.

Example 35 Wettable Powder N-ZT (4,6-dimethoxy-1,3,5-triazin-2-yl) amino-20% carbonyl] -2-chlorobenzenesulfonamide and sodium J naphthalene sulfonate 4% sodium sulphonate 4 '0 low viscosity methylcellulose 3% attapulgite 69%

The ingredients are mixed thoroughly. After grinding in a hammer mill to obtain particles, substantially all of which are less than 100 microns in diameter, the material is remixed and screened by U.S.S. Well. Through a 50 sieve (0.30 mm orifice) and packed. Example 3b 01j Suspension of N- (4,1G-dimethoxy-1,3,5-triazin-2-yl) aminocarbonyl] -benzenesulfonamide

The ingredients are combined and ground in one sand mill to give particles, essentially all less than 3 microns in diameter. The product can be used directly, diluted with oils or emulsified in water.

52 70577

Example 37

Highly concentrated N-f (4,6-dimethoxy-1,3,5-triazin-2-yl) -99% aminocarbonyl-177 benzenesulfonamide silica air gel 0.5% synthetic amorphous silica 0.5%

The ingredients are mixed and ground in a hammer mill to give a material that is substantially all permeable to U.S.S. Well. 50 sieve (aperture 0.3 mm). Concentrate can be further formed if necessary.

Example 38

Granules with a low content of N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) -1% aminocarbonyl] -2-chloro-5-methoxybenzenesulfonamide N, N- dimethylformamide a 9% attapulgite granules 90% (USS sieve size 20-40 mesh).

The active ingredient is dissolved in a solvent and the solution is sprayed onto the dedusted granules in a rotary mixer. After the spraying of the solution is completed, the stirrer is allowed to run for a short time and the granules are packed.

Example 39 Aqueous suspension of N-4,6-dimethyl-1,3,5-triazin-2-yl) - 40% aminocarbonyl / benzenesulfonamide polyacrylic acid thickener 0.3% dodecylphenol polyethylene glycol ether 0.5% disodium phosphate 1% monosodium phosphate % polyvinyl alcohol 1.0% water 56.7%

The ingredients are mixed and ground together in a sand mill to give particles, essentially all less than 5 microns in size.

it 53 70577

Example MU Solution N-Z (4-Methoxy-6-methyl-1,3,5-triazin-2-yl) -aminocarbonyl-7-2-chlorobenzenesulfonyl isamide sodium salt 5% water 95 ° C

The salt is added directly to the water with stirring to give a solution which can then be packaged for use.

Example 91 Granules N - Z "(4,6-dimethoxy-1,3,5-triazin-2-yl) aminocarbonyl] -2,5-dimethoxybenzenesulfonine dia 80% wetting agent 1% crude lignin sulfonate salt (which contains 5-20% natural sugars) attapulgite clay 9%

The ingredients are mixed and ground to pass through a 100 mesh screen. This material is then added to the fluidized bed granulator, the air stream is carefully set to fluidize the material, and a fine jet of water is sprayed onto the fluidized material. Fluidization and spraying are continued until granules of the desired diameter range are obtained. Spraying is stopped, but fluidization is continued, optionally using heat, until the water content has dropped to the desired level, usually less than 1%. The material is then removed from the device, screened to the desired diameter range, usually 14-100 mesh (1410-149 microns), and packaged for use.

E s i me rkki 4 2

Granules with a low content of N-Li4-methoxy-6-methyl-1,3,5-triazin-2-yl) - 0.1% aminocarbonyl-7-2-chlorobenzenesulfonamide 99.9% attapulgite granules (USS screen number 20-40 mesh )

The active ingredient is dissolved in a solvent and the solution is sprayed onto the dedusted granules in a twin cone mixer. After spraying the solution is complete, the material is heated to remove the solvent. The substance is allowed to cool and then packaged.

pp. 70577

Example M3 Wettable powder N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) -95% aminocarbonyl] -2-chloro-5-methoxybenzenesulfonamide dioctyl sodium sulfosuccinate 0.1% synthetic fine silica 4.9%

The ingredients are mixed and ground in a hammer mill to give particles that are substantially all less than 100 microns in size. The substance is screened by U.S.S. Well. Through a 50 sieve and packed.

Example 44 Wettable Powder N-Z "(4-methoxy-6-methyl-1,3,5-triazin-2-yl) -40% aminocarbonyl-2-chlorobenzenesulfonamide sodium lignin sulfonate 20% montmorillonite clay 40%

The ingredients are mixed thoroughly, coarsely ground in a hammer mill and then in an air mill to give particles, substantially all less than 10 microns in size. The substance is mixed again and then packaged.

The compounds of formula I can be formed using the methods of Examples 15-44.

Exploitation

The compounds of formula I are useful as herbicides. They can be used either before or after emergence to control unwanted vegetation in non-cultivated areas and to control weeds in certain cereals, e.g. wheat. Some of these compounds are useful for controlling nut Sara before and / or after emergence in crops such as cotton, corn and rice. By appropriately selecting the amount and time of application, the compounds of this invention can be advantageously used to modify plant growth.

The exact amount of a compound of formula I to be used in a given situation will vary depending on the particular end result desired, the particular application, the weeds to be controlled, the type of soil, the formulation and method of application, the weather conditions and the like. Since 70577 5 3 many variables are involved, it is not possible to determine the quantities of Jovi l y n that would be suitable for all situations. In general, the compounds of this invention are applied in amounts ranging from 0.005 to 20 kg / ha, with a preferred range of 0.01 to 10 kg / ha. Lower amounts in the area are usually selected for the lightest soils, for selective weed control in cereals or in situations where maximum continuity is not necessary. Some compounds of formula I may be used in very small amounts to modify plant growth, but higher amounts may also be useful depending on factors such as the plant being treated, the timing of treatment, etc.

The compounds of formula I may be used in combination with other herbicides and are particularly useful in combination with 3- (3,4-dichlorophenyl) -1,1-dimethylurea, Trialsins such as 2-chloro-4- Broth no) - ϋ - (isopropylamine) s-triazine in Kari, uracils such as 5-bromo-3-sec-butyl-6-methyluracil, N- (phosphonomethyl) glycine, 3-cyclohexyl-1-methyl-h-dimethylamino-s-triazine-2,4 (1H, 3H) -dione, N, N-dimethyl-2,2-diphenylacetamide, 2, With 4-dichlorophenoxyacetic acid (and related compounds), 4-chloro-2-butynyl-3-chlorophenylcarbamate (D) thin (Carbyne), diisopropylitolicarbamic acid ester, iT * \ 2 , 3-dichloroallyl alcohol (Avadex ^ 1 in), diisopropylthiocarboxylate (pham bamic acid, S- (2,3,3-trichloroallyl ester (Avadex ^ BW)), ethyl-n-benzoyl 1, i-N - (3,4-dichlorophenyl) -2-aminopropionate (r) (Suffix 'm), 1,2-dimethyl-3,5-diphenylpyrazole mmethyl sulfate (Avenge®), methyl N- [4- (2,4-dichlorophenoxy) phenoxy] propanoate (Hoeonon®), 4-amino-6-1ert. -butyl-3- (methylthio) -1,2,4-triazin-b (4H) -one (Lexone®), 3- (3,4-dichlorophenyl)] - methoxy-1- with methyl urea (Loroji® '), 3-isopropyl-1H-2,1,3-benzothiodiazine- (4) -3H-one-2,2-dioxide, o (·, ο (, σ {-trifluoro -2,6-di-nitro-N, N-dipropyl-p-toluidine, 1,1'-dimethyl, 4'-bipyridinium ion, monosodium methanesononate, 2-chloro-2 -d; with ethyl - (methoxymethyl) acetane and 1,1-dimethyl-3- (O (O, ex'-trifluoro-m-tolyl) urea (Cotorai®)) .

The activity of these compounds was observed in greenhouse tests. The tests are described and the results obtained are shown below.

56 n O 5 7 7

test method

Seeds of creeping weeds (DigiLaria species), yard grass (Echinochloa crusgalli), oats (Avena Tatua), Cassia tora, Ipomea, burdock (Xanthium species), millet, maize, soybeans, rice and wheat seeds were implanted in growth medium and treated with chemicals dissolved in plants in a non-toxic solvent before emergence. At the same time, cotton with 5 leaves (including cotyledons), shrub beans with a third leaf from a three-leaf press opening, two leaf-crawling weeds, a yard with two leaves, a single-leaf waste oat, a box with three leaves (sprayed with cotyledons) were sprayed ), four-leaf Ipomea (including cotyledons), four-leaf burdock (including cotyledons), three-leaf millet, maize with three leaves, soybeans with two Sirkka leaves, rice with two leaves, single-leaf wheat and three to five-leaf nutsedge. Treated plants and control plants were kept in a greenhouse for 16 days, then all species were compared to controls and the response to treatment was evaluated visually. Reviews for plants tested by this method are shown in Table IX.

0 = no effect & or 10 = maximum effect B = burnt C = desiccation or tissue death D = leaf fall E - emergence is prevented G = growth is slowed down H = shaping effects 1 = increased greening L = germination P = end buds die S = albinism U = unusual pigment to.i tion 6Y = buds or cocks fall VZ = retraction X = effect on leaf rubbing.

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The utility of the compounds of the invention in the selective control of weeds in wheat was first observed in a number of growth dermal tests. The four tests described below (A, B, C and D) illustrate this benefit.

Tests A

Two 25 cm diameter spherical plastic cups were filled with fertilized and limed Fallsington-1 clay soil. One cup was planted with corn, millet, and several herbaceous weeds. The following herbaceous and broadleaf species were planted: creeping weed (Digitaria sanguinalis), yarrow (Echinochloa crusgalli), oats (Avena fatua), johnson grass (Sorghum halepence), giant (Sorghum halepence); pratenssi false grass (Bromus secalinus), mustard (Brassicu arvensis), burdock (Xanthium pennsylvanicum), porcine grass (Amaranthus retroflexus), curly indigo (Aeschynomene Virginia), Ipomea species (Ipomea hede-racea), kass. , tea grass (Sida spinosa), velvet leaf (Abutilon theophrasti) and j .imson grass (Datura stramonium), as well as two 12.5 cm diameter the paper cup was filled with the doped growth layer; one was planted with rice and wheat and the other with sugar beet. These four vessels were treated before emergence, i.e., the compounds were sprayed onto the surface of the growth layers before seed germination.

28 days after treatment, the plants were evaluated. The results obtained are summarized in Table X. It should be noted that wheat tolerates the tested compounds better than most weeds.

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2 Soybeans, cotton, alfalfa, corn, rice, wheat, millet, velvet leaf (Abutilon Theophrasti), sesbania (Sesbania exaltata), cassia (Cass) were planted in 2 5 cm diameter plastic pots filled with Fallsington sludge. Ipomoea species, jimson grass (Datura stramonium), burdock (Xanthium pennsylvanicum), crawling weed (Digitaria species), nutcracker (Cyperus rotundus), yarrow (Echinochloa crusgalli) ). About 2.5 weeks after planting, the young seedlings and the growth layer around them were sprayed throughout with test chemicals dissolved in a non-toxic solvent for the plants. 14 days after treatment, all species were compared to untreated controls and their response to treatment was evaluated visually. The results obtained are shown in Table XI.

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The compounds were applied to the plants after emergence in a non-toxic solvent by spraying throughout the plantings of the following plants: wheat (height 11 cm »2-leaf stage), wasted oats (Avena fatua), (height 9 cm, 1-leaf stage), Bromus testorum (height 5 cm , In 1-leaf stage), B, secalinus (height 5 cm, in 1-leaf stage), black grass (Alopecurus myosuroides) (height 3 cm, in 1-leaf stage) and annual lolium multiforum (height 8 cm, 1-leaf stage) leaf stage), as well as plantings of the same species before germination. All plantings were in 25 cm diameter growth layer cups. Test subjects were kept in a greenhouse and evaluation of plant response was performed 5 weeks after application. The results of these tests are shown in Table XII.

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Tests D

The compounds were applied to the plants in a non-toxic solvent spray throughout the following emergent (post-emergence) planted plants: wheat, 22 cm high, Avena fatua, height IM cm, Bromus testorum, height 3 cm, Bromi secalinus, height 5 cm, , height 22 cm, Kochia scoparia, height b cm, woolly momiJle (Matricaria inodora), height 3 cm, \ additional button (Brassica arvensis), height 7 cm, Lupatorium capillifoi and buckwheat (Polygonum convolvulus), height 6 cm, and plantings of the same species before emergence, all mated in pots containing the growth layer. Test subjects were kept in a greenhouse and evaluations of seedling response were made M weeks after application to give the results shown in Table XIII.

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The following numerical values indicate the value of the compounds of this invention in controlling the nutcracker.

Root tubers of nutcracker (Cyperus rotundus) (5 per pot) were planted to a depth of about 2.5 cm in 10 cm pots containing Fallsington sludge clay. Each compound to be evaluated was applied as a growth layer surface treatment spray before emergence, directed as a tuber spray, was combined throughout the top 2.5 cm layer of the growth layer, and after emergence was sprayed on presses of seedlings about 8-10 cm high. The compounds were dissolved in a suitable solvent and applied at a spray volume of 560 l / ha. The effects of chemical treatment on seedling growth were evaluated visually 4 weeks after treatment, as shown in Table XIV.

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In another test, the compounds of this invention were found to be useful in the selective control of nutcrack in crops.

Several 25 cm diameter plastic cups lined with polyethylene liner were filled with Fallsington sludge clay and seeded with 2.5 cm deep seeds of the following plants: corn (Zea mays), soybean (Glycine max), rice (Oryza sat) , cotton (Gossypium hirsutum) and walnut nasai root tubers (Cyperus rotundus). Each compound to be evaluated was dissolved in a suitable solvent and applied before and after emergence in an injection volume of 560 l / ha. After emergence, the treated plants ranged in height from 6 to 14 cm at the time of treatment. 4 weeks after treatment, the effects of chemical treatment on plant growth were evaluated visually as shown in Table XV.

210 70577

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As will be seen in the following exams, the compounds of this invention are useful in controlling certain water weeds.

The compounds were applied to the plants in a non-toxic solvent by spraying throughout in small ponds containing seedlings of water hyacinth (Eichornia crassipes) of size? 5 to 30 cm The test subjects were kept in a greenhouse and evaluations of the plants' response were made 4 weeks after application. This test illustrates the utility of these compounds in controlling water weeds and the results are shown in Table XVI.

15 705 7 7

Ί du lock XVI

Estimates of plants react to the amount of sleep ,,

Structure yR VusilyasJUitU

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H_G 0 F

3 \ \

C - N 0} -v 1/32 9G.1C

H <\ \ -NH-C- ™ -SOr / Q \

C— n / \ - '1/16 9G1C

/ h3g CH- / 3

ςν q .N - C. 1/32 9G

II #%

HG C-SO 2 -NH-C-NH-C CH

Il H 2 \ /

HC-CH XN ~ C '1/16 9G

\ CH3 / CH3

o N - C 1/32 9G5C

II # ^

c εθ ,, - NH-C-NH-C N CH

/ S \ / 2 \ /

HC C N-C 1/16 9C

II II \ HC _CH 0-CH3 H C Cl

3 \ -m 0 \ -v 1/32 9G

// ^ "// ^ \\ HC7 C-NH-C-HH-SO ^ f f J)

\ C_N / VT- / 1/16 9G2C

h3c // 1 70577

Table XVI

Estimates of dryness react n n sit

Structure Mauru Water Hyacinth __________ kγτ ai / ha ___ H_C0 H CO.

3 \ 3 \ C ~ N 0 / - \

// ^ l! / V ^ A

HC C-NH-C-KH-SO— (()) L / 32 9G

\ / V ~ ^ Y

CZZN N- (/ \ H3CO0CH3

F1 / CH3

/ r ^ \\ n ^ A

(f)} -SO-NH-C-NH-C CH 1/32 9G

X = V xn ^ c / \ CH3 - - τ ___ 218 705 77

Table XVI

Estimates of your plant's response Amount Water hyacinth kg ai / ha

Structure cu3

, - 0 H- / 1/32 9G

\ / N— ^ 1/16 9G

Cl cu3 / - \ o N.

/.11 /

((J V — SO -KH-C-KH-C C-O-CH3 1/32 9G9C

'(\ c /

Cl c o-ci-u

J

H3C \ h3cq

. C - Hv o) -V

N C-NH-C-Nn-SO 2 - ^ f J \ * 1/32 i * G

\ - H ^ X- / / \ h3co och3 »3C- ° \ / C - N N 0 .-, ^ Η / V ~ n \

K C-HH-C-So-SO 2 - (f)) 3/22 8G

^ Cirl / \ - / / h3c- ° H_C0 Cl 3 X \

c - W 0) -V

/ \ Il // ^ λ \ h c -: ;;: - c-> u: -sor \) 1/32 lg & c \ vr_ / / \ U3C 0CH3 219 70577 C l

0 \ -v 1/32 9G7C

n C-O-C C-ra-C-Ml-SO ^ / ())

3 C, J 2Λ ^ 7 1/16 907C

! CH3 Use as Plant Growth Regulators In addition to their use as herbicides, the compounds of formula I are also useful as substances that can successfully modify the growth of selected plant species. The amounts (usually 0.01 to 1.0 kg / ha) and the timing of application are selected according to the species to obtain the desired effects with the least possible toxicity to plants. Both growth and reproduction growth can be regulated. The following examples illustrate the reactions of sugar cane, millet, Bahia and other grasses to the compounds of this invention. Sugar cane and millet produce a "chemical ripening" effect, resulting in a higher yield of soluble solids (mostly sugars). In many other herbs, growth and seedling development are limited by these compounds, which reduces movement requirements. These compounds are also useful in regulating the growth of woody and herbaceous broadleaf plants.

Example A

Dwarf sugar cane plants, 6-8 months old, with 3-5 stems (1.5-3 m tall) in a 25 cm "pot were sprayed with the compounds shown below (two pots / compound). Each stem was measured in the highest visible leaf sheath. When the stems were harvested 5 weeks after treatment, juice was extracted from them, and soluble solids were determined from the center of the upper, middle, and lower thirds of each stem.Table XVII shows that stems treated with the compounds of this invention , soluble solids were increased and growth was reduced compared to the solvent control (500 l / ha water + Tween 20® surfactant 0.2%).

220 7 0 5 7 7

Table XVII

Parts of sugar cane stalks

Growth kg / ha (cm) Bottom Middle Top

Cl o OCH3 0.25 15 18.2 17.6 11.1 / = <"/ -ς _, Ä (v Λ-SO2-NH-C-NKC (CH lo 9 l8.J 19.0 l4.6 CH3 CK, o, 00¾ 0.25 15 18.1 18.9 15Λ / = <"N-Cv (v .VsOa-NH-C-NHq 'CH 1.0 6 19.9 20.4 15.8 u = c ^ ¾

Solvent comparison 4o 16.7 1 ^ .8 6.1 C1 0 (^ DCIl3 0.25 5 I9.9 20.2 I6.8 ^^ - so2-nh-c-nh <^ Jft 1.0 4 18.8 19.9 16.6 CHa

Example B

Small sweet millet seedlings grown one per 15 cm pot to the stage just before emergence were sprayed with the following compounds. Visual effects were observed approximately 3 weeks after spraying, then after 4 weeks, the plants were harvested and soluble solids were determined in the center of the upper, middle, and lower quarters on each stalk. As shown in Table XVIII, the percentage of soluble solids increased, and growth and flowering decreased in straw treated with the compounds of this invention.

72 1 70577

Table XVIII

Soluble solids expressed as% of reference values in different parts of the millet stalk_ Mean of the 3-week response

Compound kg / ha rating 1 Bottom ..

_ ^ _ _ part Top 9 £ Ha 1.0 9G, F, 2X 114 132 69 ^^ - SO 2 -NHC-NH- ^ 'CH 4.0 9G, F 115 128' CHa CHa 9 '° CHa / = </' 4 0.03 9G, F, 5X 119 99 '34

4 / VsOs-NHC-NH-q pH

W N = q 0.5 & G, F, 3X 119 119 112 CHa 0 pH $ / = \ "1.0 8G, F, 2X 114 l40 96

ά λ-S 02-NHC-NH-C pH

'n ^ ch 0 CHa / SN "/" 4 0.125 & G, F, 1C 119 109 88

HC C-SO 2 -HH-C-IIH-Q CH

"" 2.0 & G, F 122 115 66 HC-CH CHa S, 0CK3 / - = \ 0.5 9G, F, 2X 111 100 57

4 VsOz-NHC-NH-G ^ CH

^ 'N OT 2.0 & G, F, 2X 118 105 59

Cl OCH3 0, CHa / = v ", ΓΤ = <Λ 0.5 7G 115 106 98

φ-SOa-MHC-HH- ^ CH

OCH2CH3 c 0 CHa / = <0.125 9G, F, 1C 139 115 140

4 λ-SOa-NHC-NH-tf CH

W 'N = <0.5 9G, F, 2C 147 129 146 CHa CHa 9 / ¾ / = </ -4 0.125 & G, F 113 113 114

4 Λ-soz-imc-mi-ö pH

'^ = 9 0.5 & G, F 120 113 121 CHa CHa _ i; ____ 70577

Table XVIII

Soluble traces of substances i .Assessed o: e.i.na comparable values in parts of millet stalk_ 3-week reaction

Compound k ['/ La rating 1 Lower part eski_ _ _____ part Y part F 0, CH3 / = <"0.125 & G, F, 1C 127 127 136

C> SO2-NH-C-NH- <f jCH

W = cf 0.5 & G, F, 1C 127 127 136 CHa 0 pCHa / = \ "/ N-i 0.25 & C, F 120 120 121

<λ> SO2-NHC-NH-C jCH

W NN = q 1.0 & G, F 120 120 121 CHa 0 ^ OCHa / = \ "0.25 F 120 113 107

d> SO 2 -NHC-NH-q CH

N = ((1.0 & G, F 113 113 107 OCH 3

Cl 0, CHa / = <"0.5 6G, F, 2X - 122 - O- S O2 - NHC- NH- c yn

Cl CH 3 OCH 3 C / ° 0¾ / = <0.125 9C-, F, 8X - 130

C 3 -SO 4 -NHC-NH-Q pH

^ N = C

C1 OCH3 ci o CHo / = ("0.06 9G, F, 2X - 139

(^> - SO 2 -NHC-NH-C, CH

Ii = CH

Cl 0 CH3 / = ("/ i- 0.06 & G F 2U - 165

(n / VSOa-NHC-NH-q CH

W N = cf CH- ° - ° ö & G, F, IX - I65 <\ / VsOa-NHC-NH-C CH ^

^ M

CH3 2 2 3 „Λ 70577

Table XVIII

Soluble La jährncj La expressed only in ° & as reference values in different parts of the millet stalk_ 3-vi ikon response

Yhckste kg / ha rating 1 Bottom '......

_ _____ part Upper part ci P 0, 00¾

> = <0.25 0 - 122 - (v ySOa-IiHC-IiH-C CH

^ V <OCHs o DCH3 Q "Jfstd 0.05 & G, F, 2X 119 112 116

S Oa-NHC-NH-G,, CH

n '»- (f 0.125 & G, F, 2X 155 111 105 w C Ha 0.5 & G, F, 2X 126 117 108 0 ^ OCH3 0.125 5G, F, 2X 116 107 101 <^ - so2-nhc-nh- ^ n 0.5 8g, f 115 107 115 ÖCHa 2.0 8C-, F 118 107 115 0 pHs 0> 125 gG / F / 3X 128 125 Il8 / = \ "Nq ^^ - 'SOa-NHC-NH- ^ N 0.5 9G, F 143 124 105% H3 2.0 9G, F 127 Hl 152 0 PCH3 0.125 & G, F, 1C 127 124 125

"fl-C

{^ X-SOs-NHC-NH-C 0.5 & C -,?, 2C 120 113 79

N = CH

2.0 & G, F, 2C 153 120 114

Cfl3__ 1 F * »flowering delayed 22 * 70577

Example C

Seedlings of Bahia grass (Paspaium notatum Flugge), which had well emerged in 13 cm pots, were sprayed with XIX compounds when the seed heads were just ready for emergence. The plants were about 35 cm high and three pots were sprayed from the top (C550 1 / ha) with each amount. The reaction shown in Table XIX was observed 45 days after treatment. In the invention, the compounds slowed growth and inhibited seed head development.

Table XIX

45-day Seed-kg / ha response end reviews suppression-% 0.03 2G 10 0 CHa s "^ :-( 1 0.125 2G 30

KC C-SOa-NH-C-IIH-q CH

H 11 \ = cr 0.5 3G, 2U 90 HC-CK 'CHa 1.0 3G, 2U 100 CHa 0 OCHa 0.008 2G 0 <^> - SO2-Iui-C -ΙΓΗ- <ζ CH 0.03 30 30 ^ CHa 0.125 90.1C , 2U 95 0.5 9G, 2C, 2U 95 0.008 2G 70 0 OCHa "n = (^ 0.03 70 70

/ f ^ VsOa-HH-C-HH-q CH

li-C 0.125 & G, 2C, 2U 95

Cl CHa 0.5 & G, 3C, 2U 100 ?? 5 70577

The following test results are presented to further illustrate the biological activity of the compounds of this invention. The figures describe the weed control efficiency of compounds that are selective for two important cereals, rice and wheat.

Test compounds were applied to the plants in pots filled with a growth layer in a non-toxic solvent containing intermediate hybrid rice, Japanese rice, yard grass (hehi.noohloa crusgalli) and seeds of the species Ipomoea. One compound was also applied to wheat, oats (Avena fatua), Bromus teetorum and Bromus secalinus. Emerging seedlings of some or all of the above species (after emergence) were also included in the test. Plants were kept in a greenhouse and visual evaluation of plant response was generally made approximately 3 weeks after application. The results are shown in Table XX.

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3 r0 -------- -,,,

pj 2 xsixa ιΐθίΓΓρχτιΐράρρ O O

5 * 0aJ i H -H 0 o c ΐ5ΓταθχοηχτχρΑ o m · o av aj -— * - - - —--------- c ριι / τρ Sv oj 5 <<

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n n n id is: K O O v / N.

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Claims (1)

227 705 77 Patent N- (heterocyclic aminocarbonyl) arylsulfonamides for use as herbicides and plant growth regulators, known from the formula W r1-so2-nh-c-nh-r wherein R is -ύ - <$ '' N = \ \ zz R ^ is -O-R ^ £ & '/ Γί · RM, * 8 Cs \ o' Ry Rg 9 R3 is hydrogen, fluorine, chlorine, bromine, iodine, C ^ -C ^ - alkyl-C 1 -C 4 -alkoxy, nitro, trifluoromethyl, cyano, CH 3 S (O) n "CH 3 CH 2 S or CH 3 CH 2 SO 2; R 1 is hydrogen, fluorine, chlorine, nitro or methyl; R 1 is hydrogen, fluorine, chlorine, methyl or R 1 is hydrogen, fluorine, chlorine, bromine, C 1 -C 4 alkyl-C 1-6 alkoxy, nitro, trifluoromethyl, cyano or CH 3 S (O> n; Ry is hydrogen, fluorine, chlorine, C -C 1-4 alkyl or R q is hydrogen, methyl or chlorine;% R 9 is hydrogen, chlorine or bromine; R 1-8 is hydrogen, chlorine, bromine or methyl; W and Q are independently oxygen or sulfur; or 2, X is hydrogen, chlorine, bromine, methyl, ethyl, trifluoromethyl, CHgS- or CH3OCH2-, and * 228 70S77 Z is methyl or methoxy; salts acceptable for human use; provided that a) when Rr is other than hydrogen, at least one of R 1, R 2, R 9 and R 8? is other than hydrogen and at least two of R 1, R 2, R 8 and R 11 are hydrogen; b) when R 1 - is hydrogen and none of the groups R 1> R 2, R 8 and R 11 is hydrogen, then all the groups R 1, R 2, R 8 and R 2 must be? be either chlorine or methyl; and c) when Rg and R? are each hydrogen, at least one of R 1, R 8 or R 8 must be hydrogen. II. 229 70577 N- (heterocyclic aminocarbonyl) arylsulfonamides are used as herbicides and in the form of acid-free, inverted forms In the form of WKR ^ SC * R. är 1 "V ^" rs * tfö ^ · / Λ θώ; 8 \ 8 Rs 10 R 2 is a compound, fluorine, chlorine, Bromine, iodine, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, nitro, trifluoromethyl, cyano, CH 2 SiO 2) or CH 2 CH 2 S or CH3CH2SO2; R 2 is fluorine, chlorine, nitro or methyl; R5 is fluorine, chlorine, methyl or methoxy; R8 is fluoro, chloro, bromo, C1-C4-alkyl, C1-C4-alkoxy, nitro, trifluoromethyl, cyano or CH2SCO); R? hydrogen, chloro, chloro, C 1 -C 2 alkyl or C 1 -C 2 alkoxy; R0 is methyl or chlorine; O Rg är väte, chloro eller Brom; chlorine, bromine or methyl; W och Q är oberoende av varandra syre eller svavel; n is 0, 1 or 2; X is methyl, chloro, bromo, methyl, ethyl, C 1 -C 4 alkoxy, trifluoromethyl, CH 2 S- or CH 2 OC 2 -; and Z is methyl or methoxy; och agrikorurellt salter with salter därav; förutsatt att