DK149343B - SULPHONAMIDE DERIVATIVES, HERBICIDES AND PLANT GROWTH CONTROLLING AGENTS CONTAINING THESE AND PROCEDURES FOR COMBATING WEEDS AND REGULATING PLANT GROWTH - Google Patents

Description

o 1 149343

The present invention relates to N- (heterocycloamino-carbonyl) arylsulfonamides having plant growth regulating and herbicidal activity. The invention further relates to herbicidal and plant growth regulators containing these compounds as well as methods by which the compounds are used to control weeds or regulate plant growth.

From the specification of French Patent No. 1,468,747 p-substituted phenylsulfonamides having antidiabetic effect and of formula 10 are known.

0 N

R--SO₂-NH-C-NH-- where R is hydrogen, halogen, trifluoromethyl or alkyl.

Further, from Chem.Ab., 53, 18052 g (1959), certain sulfonamides, including uracil derivatives of formula 0, are known.

20 H3C- ^ -SO2NHCNHR

N-where R is butyl, phenyl or -

V "V

Wherein R is hydrogen or methyl. In the test for hypoglycaemic action in rats (oral dose of 25 mg / 100-g), the compounds in which R is butyl and phenyl have the most potent effect. The other compounds are weak or are inactive.

From J.Acta. Polon, Pharm. 19, pages 121-125 (1962) (Chem. Ab., 59, 1633 e) it is known to prepare N - [(2,6-dimethoxypyrimidin-4-yl) aminocarbonyl] -4-methylbenzene sulfonamide of formula 35 0 _ <^ 0CH3 ch3- ^ -so2nh-c-nh- / \ ^ 0CH3 2 149343 o Based on analogy with a known compound, this compound is predicted to have a hypoglycasmic effect.

Furthermore, it is known from the specification of Dutch Patent No. 121,788 to prepare compounds of formula (1) having general or selective herbicidal activity

Cl / Q \ -S02NHCN - // ^ f (1) r4 if

10 R

Wherein R and R may individually represent alkyl of 1-4 carbon-3 4 atoms and R and R individually may be hydrogen, chlorine or alkyl of 1-4 carbon atoms.

The compounds of this invention differ structurally from the known compounds of Dutch Patent No. 121,788 in that the triazine heterocycle of the known compounds is substituted with an amino group and must furthermore contain a chlorine atom, while the compounds of this invention are not limited. thus. In addition, the sulfonylurea component of the compounds of the present invention must be unsubstituted, while the known compounds must be substituted by an alkyl group on this portion.

Studies have shown that the compounds of the present invention have a stronger herbicidal effect than those disclosed in the Dutch patent, especially in the case of finger axis and cyperus. In addition, the compounds of this invention are effective even in small quantities, which is an environmental benefit.

From J.Drug. Res. 6, 123 (1974), further, the compounds of formula A S (2> s / 2 SO 2 NHCNHR 1 where R is pyridyl) are known. These compounds can be used as antidiabetic agents.

o 3 149343

The presence of undesirable vegetation causes significant damage to useful crops, especially agricultural products, which satisfy the human's basic needs for food and fiber, e.g. cotton, rice, corn, 5 wheat, soybean and similar crops. The current population explosion and the simultaneous global shortage of food and fiber necessitates increased efficiency in the production of these crops. Avoiding or reducing the loss of a portion of these valuable crops 10 by eradicating or inhibiting the growth of undesirable vegetation is one way to increase this efficiency.

There are many different materials that can be used to eradicate or inhibit the growth of undesirable vegetation, and such materials are usually referred to as herbicides. However, there is a great need for more effective herbicides that destroy or control weeds without causing significant damage to the useful crops. Some weed species, especially cyperus, are very difficult to control, and many 20 of the herbicides used to control cyperus have so little selectivity that they cause damage to the crops themselves.

In accordance with the present invention, there are provided novel compounds of formula I and agriculturally suitable salts thereof, suitable agricultural agents containing these compounds, and methods of using them as selective as well as general herbicides having both pre-energetic and post-energetic effects. The compounds have strong herbicidal activity. They are particularly useful for the control of cypress, as they cause only minimal damage to the desired crops such as cotton, rice, corn, wheat and the like. The compounds in question are peculiar in that they have the general formula

W

R 1 -SO 2 -NH-C-NH-R I

where 4

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149343 R is x x

$ —F $ —S

or -f VN

5 - "1. R is 3 4 RJ li · fQ \ · or 1 ° e7 / \ r6 J? Q and R 10 15 3 6 R and R respectively are hydrogen, fluoro, chloro, bromo, iodo, C 1-4 alkyl, alkoxy, nitro, trifluoromethyl, cyano, CH, S (O) - or CH-CH-S (0) -, λ o in 3 2η R * means hydrogen, fluorine, chlorine, bromine or methyl, 20 R "* means hydrogen, fluorine, chlorine, bromine, methyl or methoxy, 7 R means hydrogen, fluorine, chlorine, bromine , C1-4 alkyl or C1-2 alkoxy, g R means hydrogen, methyl, chlorine or bromine, R 10 and R each independently represent hydrogen, methyl, chlorine or bromine, W and Q each represent oxygen or sulfur, n is 0, 1 or 2, X means hydrogen, chlorine, bromine, methyl, ethyl, alkoxy, trifluoromethyl, CH 2 S- or CH 2 OCH 2 - and Z means methyl or methoxy, and their agriculturally suitable salts, except that when 5 a) R is different from hydrogen, at least one of the substituents R 1, R 2, R 2 and R 2 is different from hydrogen, 35 and at least two of the substituents R, R ', R R 'is hydrogen,

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B) R · is hydrogen and the subsets of the R R, R R, R6 and R R substituents are all different from hydrogen, the substituents R ^, R4, R ^ and R7 are all either chlorine or methyl, and 37 7 c) R and R both represent hydrogen, at least one of the substituents R, R or R is hydrogen.

The compositions according to the invention are characterized in that they contain the above-mentioned compounds, and the methods according to the invention are characterized in that the compounds are applied to the vegetation or the growing site.

Preferred compounds due to effect or cost or both are compounds of formula I as defined above, wherein R 2 represents R 7 R 6 3 and R represents hydrogen, fluoro, chloro, bromo, alkyl, C 1-4 alkoxy 'CH 3 S CH 3 CH 2 S-, 5 R means hydrogen, fluorine, chlorine, bromine or methyl, and island R represents hydrogen, fluorine, chlorine, bromine, C 1-4 alkyl, C 1-4 alkoxy, trifluoromethyl, nitro, CH 2 S- or CH 2 Cl 2 S-, 25 however, when a) R 1 is different from hydrogen, R 2, R 4, R 7 and R must each mean hydrogen, fluoro, chloro, bromo, methyl or methoxy, and when R is said pyrimidinyl group. pey is X methyl or C1-3 alkoxy and Z is methyl or methoxy or when R is said triazinyl group, X is methyl or C3-3 alkoxy and Z is methoxy.

Also preferred compounds because of effect or price or both are compounds of formula I as defined above, wherein R, R and R have the and R when R is said pyrimidinyl group, Q is sulfur, X is methyl or alkoxy and Z is methyl or methoxy or when R is said triazinyl group, Q is sulfur, X is methyl or alkoxy and Z is methoxy. .

Particularly preferred compounds because of their excellent effect or extremely advantageous price or both are the following: 1) N - [(4-methoxy-6-methylpyrimidin-2-yl) aminocarbonyl] -2-10-chlorobenzene sulfonamide, m.p. 194-196 ° C, 2) N-1 (4,6-dimethoxypyrimidin-2-yl) aminocarbonyl] -2,5-dichlorobenzenesulfonamide, m.p. 189-190 ° C, 3) N - [(4-methoxy-6-methylpyrimidin-2-yl) aminocarbonyl] -2-methylbenzenesulfonamide, m.p. 172-174 ° C, 4) N - [(4,6-dimethylpyrimidin-2-yl) aminocarbonyl] -2-thiophenesulfonamide, 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, 6) N - [(4,6-dimethoxy-1,3,5-triazin-2-yl) aminocarbonyl] -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.

Although all the compounds of formula I have herbicidal activity, they do not have all selective effect on all 25 crops. However, by selecting the compound concerned, weed control and crop protection can be achieved.

Thus, some of the compounds have particular selectivity in controlling weed species in wheat and rice, cyperus control in crops such as maize, cotton, soybean or rice, shrub control and water hyacinth control. Furthermore, the compounds of formula I can be used as plant growth regulators, e.g. to increase the sugar content of sugar cane and sorghum and to suppress seedhead formation in grasses such as Bahia grass.

35

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Particularly preferred are: A) For selective control of wheat weeds: 1) N - [(4-methoxy-6-methylpyrimidin-2-yl) aminocarbonyl] -2-chloro-5-methoxybenzenesulfonamide, m.p. 199-200 ° C, 2) N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) aminocarbonyl] -2-chlorobenzenesulfonamide, m.p. 174-178 ° C, 3) N - [(4,6-dimethoxy-1,3,5-triazin-2-yl) aminocarbonyl] -2-chlorobenzenesulfonamide, m.p. 188-189 ° C and 4) N - [(4,6-dimethoxy-1,3,5-triazin-2-yl) aminocarbonyl] -2,5-dimethoxybenzenesulfonamide, m.p. 187-188 ° C.

B) For selective control of crops in crops: 1) N - [(4,6-dimethoxypyrimidin-2-yl) aminocarbonyl] -2,5-dichlorobenzenesulfonamide, m.p. 189-190 ° C and 2) N - [(4,6-dimethylpyrimidin-2-yl) aminocarbonyl] -2,6- dichlorobenzenesulfonamide, m.p. 177-182 ° C.

C) To control water hyacinth: 1) N- [4-methoxy-6-methylpyrimidin-2-yl) aminocarbonyl] - 20 -2-chlorobenzenesulfonamide, m.p. 194-196 ° C, 2) N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) aminocarbonyl] -2-chlorobenzenesulfonamide, m.p. 174-178 ° C, 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) aminocarbonyl] -2-chloro-5-methoxybenzenesulfonamide, m.p. 175-176 ° C.

D) For growth regulation: 1) N - [(4,6-dimethylpyrimidin-2-yl) aminocarbonyl] benzenesulfonamide, m.p. 228-230 ° C, 2) N - [(4,6-dimethoxypyrimidin-2-yl) aminocarbonyl] -2,5-dichlorobenzenesulfonamide, m.p. 189-190 ° C, 3) N - [(4,6-dimethoxy-1,3,5-triazin-2-yl) aminocarbonyl] benzenesulfonamide, m.p. 183-185 ° C, 8

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4) N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) aminocarbonyl] -benzenesulfonamide, 5) N - [(4,6-dimethyl-1,3,5-methyl) triazin-2-yl) aminocarbonyl] benzenesulfonamide, m.p. 200-201 ° C and 5 6) N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) aminocarbonyl] -2-chlorobenzenesulfonamide, m.p. 174-178 ° C.

E) For selective weed control in rice: 1) N - [(4-methylpyrimidin-2-yl) aminocarbonyl] -2-chlorobenzene sulfonamide, m.p. 201-203 ° C and 2) N - [(4,6-dimethoxypyrimidin-2-yl) aminocarbonyl] -2,5-dibromobenzenesulfonamide, m.p. 201-204 ° C.

F) For selective shrub cover; N-1 (4,6-dimethoxy-1,3,5-triazin-2-yl) aminocarbonyl] benzenesulfonamide, m.p. 183-185 ° C.

As illustrated in Scheme 1 below, the compounds of formula I can be prepared by reacting an appropriate 2-aminopyrimidine or 2-amino-1,3,5-triazine of formula III with an appropriately substituted sulfonyl isocyanate or isothiocyanate of formula II wherein R 1 , W, X, Z and R have the above meanings.

Scheme 1.

25 W

The reaction is best carried out in an inert aprotic organic solvent such as methylene chloride, tetrahydrofuran or acetonitrile at atmospheric pressure and room temperature. The method of addition is not critical. However, it is often convenient to add the sulfonyl isocyanate or iso-

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The thiocyanate for a stirred suspension of the amine of formula III. Since such isocyanates and isothiocyanates are usually liquids, their addition can be readily regulated.

The turnover is usually exothermic. In some cases, the desired product is insoluble in the hot reaction medium and crystallizes from it in pure form. Products which are soluble in the reaction medium are isolated by evaporation of the solvent, trituration of the solid residue with a solvent such as 1-chlorobutane or 10 ethyl ether and filtration.

In some cases, it is possible to prepare an isomer product by the reaction shown in Scheme 1. Such isomer products can be formed by adding compound II to the endocyclic nitrogen atoms in amine 15 III and having the structure exemplified below:

w \ N «V M

R -'- SO ^ HC -] ^^ -X, R1SQ2NHC— ^^ -Z

Z "Xr 20 or * Ψ r1-so9nhc-n ^ n 25 z-AA'x

The sulfonyl isocyanates of formula II (where W means 0) can be prepared by reacting similar sulfonamides with phosgene in the presence of reflux n-butyl isocyanate in a solvent such as chlorobenzene using the method of H. Ulrich and A.A.Y. Sayigh, Newer Methods of Preparative Organic Chemistry, Vol. VI, pages 223-241, Academic Press,

New York and London, W. Foerst Ed. In cases where the desired sulfonyl isocyanate is formed in poor yield using the above process, sulfonylurea substance formed by reaction of butyl isoyanate with the appropriate sulfonamide can be reacted with phosgene as described in the above reference.

The preparation of the sulfonamides from ammonium hydroxide and sulfonyl chlorides is widely described in the literature, cf. eg. 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 best prepared by chlorosulfonation of a substituted benzene, naphthalene or thiophene in carbon tetrachloride using the method of H.T. Clarke et al., Org. Synth. Coll.

15 Vol. 1, 2nd Edition, 1941, page 85. Other benzenesulfonyl chlorides are best prepared by diazotizing the appropriate aniline with sodium nitrite in hydrochloric acid followed by reaction of the diazonium salt with sulfur dioxide and cuprochloride in acetic acid using the procedure of 20 H.L. Yale and F. Sowinski, J. Org. Chem. 25, 1824 (1960).

Furanesulfonyl chlorides are best prepared as shown in Reaction Scheme 2 below.

Kea kt ion s s schema 2.

25 - A + 0 - SO + - O + η-Εηω - »0'Li ^ 3 ° C12 £> 30.01 h2o / hci 35 o 149343

Sulfonyl isothiocyanates can be prepared by treating sulfonamides with carbon disulfide and potassium hydroxide, followed by reaction of the dipotassium salt with phosgene according to the method of K. Hartke, Arch.

Pharm., 299, 174 (1966).

The synthesis of heterocyclic amine derivatives is described in "The Chemistry of Heterocyclic Compounds", published by Interscience Publ., New York and London. The 2-aminopyrimidines are described by D.J. Brown in "The Pyrimidines", Volume 10 XVI in the above work.

Agri-culturally suitable salts of the compounds of formula I are also useful herbicides and can be prepared in a variety of known ways. For example, metal salts can be prepared by treating compounds of formula I with a solution of an alkali metal or alkaline earth metal salt with a sufficient basic anion, e.g. a hydroxide, alkoxide, carbonate or hydride. Quaternary ammonium salts can be prepared in a similar manner.

Salts of the compounds of formula I can also be prepared by exchanging one cation with another. Cation exchange can be effected by directly treating an aqueous solution of a salt of a compound of formula I, e.g. an alkali metal salt or quaternary amine salt, with a solution containing the cation to be exchanged. This process is most effective when the desired salt containing end of the exchanged cation is insoluble in water and can be isolated by filtration.

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 salt or a quaternary ammonium salt, through a column packed with a cation exchange resin containing the cation to be exchanged. In this process, the cation in the resin is exchanged with the cation in the original salt and the desired product is eluted from the column.

This process is particularly useful when the desired salt is water-soluble.

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12 169343

Acid addition salts which can be used in the present invention can be obtained by reacting a compound of formula I with a suitable acid, e.g. p-tcbuenesulfonic acid, trichloroacetic acid or similar acids.

The compounds of the invention as well as their preparation are further illustrated in the following examples wherein all temperatures are given in ° C.

Example 1 N - [(4,6-Dimethylpyrimidin-2-yl) aminocarbonylbenzenesulfonamide

To a dry, thoroughly stirred solution of 12.4 g of 2-amino-4,6-dimethylpyrimidine in 250 ml of methylene chloride at room temperature and atmospheric pressure is added dropwise 18.3 g of benzene sulfonyl isocyanate. The resulting mixture is stirred for 2 hours, after which the precipitated product is filtered off. After washing with 1-chlorobutane, the product melts at 228-230 ° C and has characteristic absorption bands in the IR spectrum at 1710, 1620 and 1550 cm. The product is N - [(4,6-dimethylpyrimidin-2-yl) aminocarbonyl] benzenesulfonamide.

20

Example 2 N - [(4-Methoxy-6-methylpyrimidin-2-yl) aminocarbonyl] -2- chlorobenzenesulfonamide

To a suspension of 280 g of 2-amino-4-methoxy-6-methyl-pyrimidine in 2000 ml of methylene chloride is added 434 g of 2-chlorobenzenesulfonyl isocyanate with stirring. The resulting mixture is stirred for 16 hours, cooled to 10 ° and filtered to give 470 g of a solid, m.p. 195-196 °. Mass spectrographic analysis shows that the product has a molecular weight of 306.

Analysis for C- HH ^CINO ^O ^S

Calculated: C 43.89% H 3.40% N 15.75%

Found: C 43.47% H 3.56% N 15.30% This product is N- (4-methoxy-6-methylpyrimidin-2-yl) aminocarbonyl] -2-chlorobenzenesulfonamide.

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13 U9343

By partial evaporation of the filtrate, 20 g of by-product is precipitated with m.p. 160-162 °. The IR spectrum of this by-product corresponds to the IR spectrum of the first precipitate and the product has a molecular weight of 356.

Analysis for C13H13C1N0404S:

Calculated: C 43.89% H 3.40% N 15.75%

Found: C 44.09% H 3.56% N 14.97% 10 Using an equivalent amount of a suitable 2-aminopyrimidine and a suitably substituted benzenesulfonyl isocyanate, the following compounds of Formula I can be prepared using the 1 and 2 described methods: 15 20 25 1 35 14 149343 R6 R7 CH, • 5> - <"" 3 r3 - // Vso2-nhcnh- / \ R4 R3 'Ch3 ___r4 r5_R ^ _R ^ _Smp. in ° C (d) = decomposition Η Η Η Η H 228-230 F Η Η Η H 218-219 CH3 Η Η Η H 195-196

Cl 4 Η Η H 204-205 Η Η H N02 H 193-196 Η Η H CF3 H 183 (d) H Cl Η Η H 142-143 -CF3 Η Η Η H 218-220 CH30- H CH3 ° "HH 198 -199 CH3 Η H N02 H 191-192 CH3 H 'H -CH (CH3) 2 H 157-160 CH3 Η H Cl H 209-211

Cl Η H CH3 H 211-213 F Η H F H 189-190 CH3 Η H CH3 H 193-194

Cl Η Η H CH3 230-232 N02 H Cl Η H 210-212

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 CH3 H CH3 H CH3 227-231 (d) F H F H F 173-180

Cl H Cl H Cl 208-210 CH30- H CH30- H CH30- 192-193

Cl Cl H Cl Cl 220-222 CH3 CH3 H CH3 CH3 244-246

Cl Cl Η Η H 195-197

Cl CH3 Η Η H 196-199 15 149343 _R ^ _R ^ _R ^ _R ^ _R ^ _Smp. in ° C (d) - Specification CH30- Cl Η Η H 179-180 F Cl Η Η H 196-197 CH3 Cl Η Η H 208-209

Cl H Cl Η H 202-205 FH Cl Η H 202-203 H Cl Cl Η H 210-212 H Cl H Cl H 199-202 CH30 H Cl CH30 H 202-203 F Η H CH3 H 210-212 CH3 Η HFH 200-201

Cl Η H ch3 ° - H 198-199

Br Η H Br H 211-212 CH30- Η H CH3 ° - h 193-195 CH3 Η H CH3 H 204-205 CH3 Η H Br H 205-207 C2H50- Η H C2H50- H 208-210 CH30- Η HFH 199 -201

Cl Η H Cl H 212-213 CH3CH2CH20 Η H CH3CH2CH20 H 150-152 CH30- Η H Cl H 209-210 CH3 CH3 H N02 H 221-223 16 149343

Table I-B

Ri R7 n AND

ΝΝ_ / ° N _- ^ 3 R - // \ -SO „NHCNH - (/ \\

W / nW

R4 ^ V ^ CH3

r3 R4 R5 R6 R7 Mp. in ° C

20 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 CHjO Η Η Η H 178-180 CH3 Η Η Η H 172-174 -S02CH3 Η Η Η H 170-171 H Cl Η Η H 151-153 Η Η H CF3 H 150-152

Cl Cl Η Η H 199-200

Cl CH3 Η Η H 177-186 CH30- Cl Η Η H 190-193 CH3 Cl Η Η H 190-192 F Cl Η Η H 193-195 H Cl Cl Η H 193-195 n-C4HgO- Η H n-C4H90 - H 182-183 FH Cl Η H 206-208 NO 2 HH Η H 223-225 CF3 HH Η H 194-197

Cl H F H H 199-201

Cl H Cl Η H 195-197- CH3 Cl H Cl H 187-189 CH30 H CH30 Η H. 182-184 Η H CH30 N02 H 211-213 H Cl H Cl H 207-211 H CH3 CH3 Η H 193-196 F Η HFH 177-178 CH30- Η H Cl H 199-200 CH3 Η H Cl H 206-207 17 149343 __R ^ _R ^ _R ^ _Smp. i ° C_

CoHc0- Η H ¢ ,, 11-0- H 175-177 2 5 2 b

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

Cl Η Η H Cl 148-153

Cl Η Η H CH3 166-17 0 CH3S- Η Η Η H 200-202 C2H50- Η H Cl H 180-183 CH30 H Cl CH30 H 173-175 CH3CH2CH20. 17 H CH3CH2CH20 H 173-175 CH-jS Η H Cl H 215-216 CH3 CH3 H N02 H 191-193

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 CH3 ° - H CH3 ° 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 N02 H 182-183

Table I-C

18 149343: "v /: f-F *

ΈΓ-μ '\ -S02NHCNH- / r A

R4 ^ \ 3 N NOCH3 _R ^ _R ^ _R3__R ^ _ Snip, i ° C _ Η Η Η Η H 202-203 F Η Η Η H 200-201

Cl -1 Η Η H 179-181 CH3 Η Η Η H 184-186 H Cl Η Η H> 250 Η Η H CF3 H 190-191 F H H H F 213-215

Cl Η Η H Cl 192-194 NO 2 H Cl Η H 196-198 NO 2 Η Η Η H 219-220 CH3S Η H Cl H 211-213 CH30- Cl Η Η H 183-184 F Cl Η Η H 244- 245 FH Cl Η H 223-224

Cl H F Η H 203-205

Cl H Cl Η H 190-191 CH30- H CH30 Η H 182-184 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 ch3 ° - h 198-199 CH3 Η H Br H 170-172

Cl Η H N02 H 225-228

Cl Η H CH3 ° ~ h 180-181 C3H? 0- Η H C3H7 ° h 188-189 nC ^ HgO- Η, H n-C4H90- H 165-167 C ~ H_0- Η H C0H, -0- H 181 -183 CH30- Η HFH 192-194 CH30- Η H Cl H 197-198 19 149343 __R ^ __ Mp. i ° C_

Cl Η H Cl H 189-190 CH3 Η H Cl H 181-183

Cl Η H CH3 H 216-217 CH3 Η H N02 H 205-207 CH3 Η H -CH (CH3) 2 H 110-116 CH3 Η H CH3 H 187-189 CH30- H ch3 ° - Η H 173-175 CH30 Η 19 Η H 193-195 CH30 H Cl CH30 H 141-143 CH3 Cl H Cl H 186-189 (CH3) 2CH Η H (CH3) 2CH H 161-163 CH3S Η Η Η H 211-214 Η H CH30 N02 H 210 -212

Cl Η Η H CH3 171-174 CH3 H CH3 H CH3 197-198 F H F H F 219-221

Cl H Cl H Cl 194-195 CH30- H CH3 ° - H CH3 ° ~ 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 H N02 H 207-209 CH3 CH3 H N02 H 225-227

Table I-D

20 149343 R6 R7: wr 2 n_ ^ ch3 r5- \ 7-SO2NCNH “{f / _rHs ° _

R3 R4 R5 R6 R7 X Mp. in ° C

__ (d) = decomposition_ H H H H HH 187-189 CH3 Η Η Η H -CH2OCH3 157-158

Cl H H Η H -CH2OCH3 179-180

Cl Η H Cl H -CH2OCH3 174-176 CH30- Η H CH3O- H -CH2OCH3 155-157 F Η Η Η Η H 192-193 CH3 Η Η Η Η H 211-213

Cl Η Η H HH 201-203 H Cl Η H HH 198-199 F Cl HHHH 219-220 CH3 Cl Η Η Η H 211-213 FH Cl H HH 222-235 (d) H Cl H Cl Η H 201-203 CH30- Η H Cl Η H 224-226

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

Cl Η Η H Cl H 160-163 Η Η Η H C2H5 ° “180-182 Η Η Η Η H (CH3) 2CHO- 116-120 Η HHHH Cl 213-215 H Cl Η Η H Cl 194-195 Η Η Η Η H CH 3S- 208 (d) 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 N02 Η Η Η H Cl 170-172

Table I-E

21 149343 R6 R7 0 ° ΰΗ3 r5 “\ Vso2nhchh- $ \ r4> Ke3 - <s

R3 R4 R5 R6 R7 X Mp. in ° C

_ (d) = decomposition_ Η Η Η Η Η H 199-200 (d) Η Η Η Η H Cl 181-183

Cl 185 Η Η H Cl 185-188 CH3 Η Η H Cl 176-178 Η Η Η CH H CH3S “194-196 Η Η Η Η H-CF3 164-168

Cl Η Η: .H H -CF3 204-208 CH3 Η Η Η H -CF3 171-173 Η Η H -CF3 H -CF3 191-194 Η Η Η Η H C2H5 ° 163-165

Cl Η Η Η H C2H5 ° 142-144 CH3 Η Η Η H C2H5 ° 148-149 22

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149343

Example 3 N - [(4,6-Dimethylpyrimidin-2-yl) aminocarbonyl] -2-thiophenesulfonamide

To 12 g of 2-amino-4,6-dimethylpyr imidine in 250 ml of acetonitrile is added with stirring 19 g of 2-thiophenesulfonylisocyanate.

The resulting mixture is stirred for 2 hours and filtered to give the desired solid product, m.p. 215-216 °. The IR spectrum of this product shows absorption peaks at 1540, 1605 and 1700 cm -1.

10

Example 4 N - [(4,6-Dimethylpyrimidin-2-yl) aminocarbonyl] -2,5-dichloro--3-thiophenesulfonamide

To a suspension of 12 g of 2-amino-4,6-dimethylpyrimidine in 300 liters of methylene chloride is added at room temperature 26 g of 2,5-dichloro-3-thiophenesulfonylisocyanate. After stirring for 16 hours, the solution is evaporated to dryness and the desired product is obtained as a solid residue which is triturated with ethyl ether and filtered. The solid product thus obtained melts at 192-194 ° and has IR absorption peaks at 1550, 1605 and 1690 cm -1.

Example 5 N - [(4-Methoxy-6-methylpyrimidin-2-yl) aminocarbonyl] -2-furanesulfonamide

To a solution of 2.10 g of 2-furanesulfonyl isocyanate in 40 ml of methylene chloride is added 1.60 g of 2-amino-4-methoxy-6-methylpyrimidine. The resulting mixture is stirred for 1 hour at room temperature and then refluxed for 15 minutes, after which the solvent is removed under vacuum. The resulting solid was placed under ethyl ether containing traces of acetonitrile for 1 day, then filtered and dried to give the desired product, m.p. 185-188 ° (dec.).

35 23

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U9343

Using an equivalent amount of an appropriate 2-aminopyrimidine and an appropriately substituted thiophene or furanesulfonyl isocyanate, the compounds listed below in Table II can be prepared using the procedures set forth in Examples 5 to 3.

Table II-A

10

X

-SO "NHC-NH-Z" -y-H

r8 / \ q / 11 = / 15 _Q X_Z_Smp. i ° C_ H S CH3 CH30- 207-208 H S CH3O- CH30- 206-207 20 Cl S CH3 CH30- 186-187

Cl S CH3 CH3 198-199

Cl S H CH3 197-198 H O CH3 CH30 185-188

Table II-B

λ x "3—

S 02NHCNH- / \\ -H

- R9_R10 1_X_Z_Smp. i ° C_

Cl Cl CH, CH, 0- 186-188 35 ^ 3

Cl Cl CH30- CH30- 201-202 U9343 24

ISLAND

Example 6 N - [(4,6-Dimethoxypyrimidin-2-yl) aminocarbonyl] -1-naphthalenesulfonamide

To a suspension of 15.6 g of 2-amino-4,6-dimethoxy-pyrimidine in 400 ml of acetonitrile is added 23.3 g of 1-naphthalenesulfonylisocyanate with stirring. After continued stirring for 14 hours, the desired solid product is filtered off, which after washing with a small amount of ethyl ether melts at 177-178 °.

Using an equivalent amount of a suitable 10-aminopyrimidine and 1-naphthalenesulfonyl isocyanate, the following compounds of formula I can be prepared using the procedure described in Example 6:

N - [(4-chloro-6-methylpyrimidin-2-yl) aminocarbonyl] -15 -1-naphthalenesulfonamide, m.p. 205-207 ° C

N - [(4,6-dimethylpyrimidin-2-yl) aminocarbonyl] -1-naphthalenesulfonamide, m.p. 201-202 ° C N - [(4-methylpyrimidin-2-yl) aminocarbonyl] -1-naphthalenesulfonamide, m.p. 182-183 ° C

N - [(4-methoxy-6-methylpyrimidin-2-yl) aminocarbonyl] -1-naphthalenesulfonamide, m.p. 210-211 ° C N - [(4,6-dimethoxypyrimidin-2-yl) aminocarbonyl] -1-naphthalenesulfonamide, m.p. 177-178 ° C. 1 2 3 4 5 6 7 8 9 10 11

Example 7 2 N - [(4,6-Dimethylpyrimidin-2-yl) aminothioxomethyl] benzenesulfonamide

To a dry suspension of 12.4 g of 2-amino-4,6-dimethyl-pyrimidine in 60 ml of acetonitrile is added 19.9 g of benzenesulfonyl-6-isothiocyanate. The heavy white precipitate formed is filtered off 7 and washed with anhydrous ethyl ether. The product has m.p. 165-8 -170 ° and is N- [(4,6-dimethylpyrimidin-2-yl) aminothioxomethyl] - 9 benzenesulfonamide.

10

By using an equivalent amount of the appropriate 11 sulfonyl isothiocyanate and an appropriately substituted aminopyridine, the compounds listed in Table III below may be used.

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is prepared using the method of Example 7:

Table III-A

R7 ο X

Λ-π N- / R - // Xy-SO NHC-NH - // \> 10 r4 ^^ r3 R3 R4 R5 R6 R7 X Z_Smp. i ° C_ Η Η Η Η H CH3 CH30- 188-189 15 Η Η Η Η H CH30 CH30 192-193

Cl Η Η Η H CH3 CH30- 184-185

Cl Η Η Η H CH30- CH30- 169-172 CH3 HHHH CH3 CH30 165-167 CH3 Η Η Η H CH30- CH30- 181-182 20 CH3 ° "hh CH3 °" H CH3 CH3 ° “178-180 CH30- Η H CH30- H CH30- 'CH30- 191-193

Table III-B 25

S X

"N S '// -SO-NHCNH- (/ vv r8As / 2 30 _X_Z_Smp. I ° C_ H CH3 ch3 ° - 196-197 H CH30-CH30-202-204 35 26 149343

ISLAND

Example 8 2-Furanesulfonyl isocyanate

. O Ov ^ <fY

\ o / Δ ^ ° '\ l "30 ^ 0X \ S02Li 10 Cl2 / ~ \ NH4 ° H / t ~ \ excess (C0C1) 2 H20' HC1 'XoA.so.ci- ^' \» A ^ S02NH2 15 A. lithium-2-furanesulfinate 20

To a solution of 39.6 g of furan (585 mmol) in 200 ml of anhydrous ethyl ether is carefully added under a nitrogen atmosphere 400 ml of 1.6 M n-butyllithium in hexane keeping the reaction temperature at 30 ° or less. The mixture is stirred until complete precipitation has occurred. After cooling to -25 to -30 °, excess gaseous sulfur dioxide is slowly passed through the mixture over 2 hours. The mixture is stirred at room temperature for a further 90 minutes and the precipitated lithium-2-furanesulfinate is filtered off and washed with acetone.

Mp. 250 ° C. IR (nujol) 3400-3000 cm "1 (W), 1700 cm" 1, 1550 cm -1 (VW), 1210 cm "1, 1140 cm" 1, 1115 cm "1 (m), 1020 cm" 1 ( VS), 910 cm "1, 880 cm" 1, 825 cm "1 (W), 735 cm" 1 (S).

35 149343

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27 B. 2-Furanesulfonyl chloride 90 ml of water, 410 ml of concentrated hydrochloric acid and 68.0 g of lithium-2-furanesulfinate are stirred and cooled to 10-15 °.

12.3 ml (39.4 g) of liquid chlorine are added dropwise over 5 of 30 minutes. The mixture is stirred for an additional 30 minutes at 5 °, poured on ice and extracted with methylene chloride. Evaporation of the methylene chloride gives 44 g of 2-furansulfonyl chloride with b.p. 95 ° at 7 mm Hg.

IR (pure) 3400 (m), 3120, 1800, 1550 (m), 1450 (S), 1380 (US), 1210, 1160, 1120 (US), 1035 (m), 1010 (US), 913, 882 (S).

C. 2-Furanesulfonamide 23 g of 2-Furanesulfonyl chloride (138 mmol) is added dropwise to 200 ml of concentrated NH 2 OH at 0-5 °. After stirring overnight at room temperature, the water is removed in vacuo and the precipitate is washed with ice water and dried. Yield 14 g of 2-furanesulfonamide.

Mp. 120-122 ° C. (literature mp 120-122 ° C: 20 JOC 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" 1 (S). 1 2 3 4 5 6 35 D. 2-Furanesulfonyl isocyanate 2 150 ml of dry toluene, 25 ml of oxalyl chloride (295 mmol) 3 and a trace amount of diazabicyclo [2.2.2] octane (DABCO) are heated 4 to 90 °. 10 g of 2-furanesulfonamide are added over 15 ml of 5 nuts and the mixture is kept at 95 ° for 2 hours. After filtration, the solvent is removed in vacuo to give 2.1 g of an oil exhibiting the characteristic isocyanate absorption in the IR spectrum (2280 cm 1).

28 149343

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Example 9 N - [(4,6-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 is added, with stirring, 19.7 g of 2-methylbenzenesulfonylisocyanate at a rate to avoid vigorous heating. of the reaction mixture. Stirring is continued until the desired product crystallizes. The product is filtered off, washed with a small amount of ethyl ether and dried. 10 N - [(4,6-dimethyl-1,3,5-triazin-2-yl) aminocarbonyl] -2-methylbenzenesulfonamide is obtained, m.p. 141-145 ° C.

Example 10 N- [(4,6-Dimethyl-1,3,5-triazin-2-yl) aminocarbonyl] -2-chlorobenzenesulfonamide

To 12.3 g of 2-amino-4,6-dimethyl-1,3,5-triazine in 200 ml of acetonitrile is added with stirring 21.7 g of 2-chlorobenzenesulfonyl isocyanate. All the solid dissolves after the reagents are added and the mixture is then evaporated to dryness.

The solid residue is triturated with ethyl ether and filtered to give crude N - [(4,6-dimethyl-1,3,5-triazin-2-yl) -aminocarbonyl] -2-chlorobenzenesulfonamide, m.p. 115-118 ° C. The NMR absorption spectrum of this product in trifluoroacetic acid shows a singlet of 2.69 and 2.9 ppm.

25

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-1,3,5-triazine in 300 ml of dry methylene chloride containing 0.1 g of 1,4-diazabicyclo [2.2.2] octane is added 21 g of 2- chlorobenzene sulfonyl isocyanate with stirring. The mixture is stirred for 16 hours and the solid formed is filtered off. After washing the solid with 1-chlorobutane, the resulting product, N - [(4,6-dimethoxy-35-1,3,5-triazin-2-yl) aminocarbonyl] -2-chlorobenzenesulfonamide is obtained.

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149363 with m.p. 188-189 ° C. IR absorption analysis shows absorption peaks at 1740, 1630 and 1595 cm which is typical of this type of compound.

By using the procedure described in Examples 9-11 with an equivalent amount of the appropriate aminotriazine and the appropriately substituted sulfonyl isocyanate, the compounds listed below in Table IV can be prepared:

Table IV-A

10 __ ° N_ /

^ y-SO2NHCNH- ^ S

^ Z

15

X Z Mp. in ° C

CH3 CH3 200-201 CH30 CH30 183-185 20 CH30 CH3 166-171 CH3CH2CH20 CH30 121-124 CH3S CH30 197-199

Table IV-B 25 0 "_ / x Q-SO-NHCNH - / a 3" = <

R · 3 ^ Z

R? X Z Mp. in ° C

CH3 CH30 CH3 158-162 35 CH3 CH30 CH30 144-147 CH3 CH3OCH2 CH3 147-150

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149343

3Q

X Z Mp. in ° C

CH3 CH3S CH30 191-193

Cl CH3 CH3 185-187

Cl CH30 CH3 174-178 5 Cl CH30 CH30 188-189

Cl CH3OCH2 CH3 142-145

Cl CH3CH20 CH3 117-121

Cl CH3CH20 CH30 132-133 F CH30 CH3 168-172 10 F CH30 CH30 169-175 CF3 CK3 CH3 172-174 CF3 CH3 CH30 165-167 CF3 CH30 CH30 171-173 N02 CH3 CH30 178-181 (decomposition) 15 N02 CH30 CH30 175-178 F CH3CH2 CH3 168-170 N02 CH3 CH3 105-110 CH3S CH30 CH3 181-184 CH3S CH30 CH30 171-174 20

Table IV-C

o N_ / 1 25 // -SO-NHCNH- W \ = K- 35

Z Mp. in ° C

Cl CH, CH, 190-191 30 ^ J v.

Cl CH30 CH30> 250 CF3 CH3 CH3 158-162 CH3 CH3 CH3 184 (solidifies) CH3 CH30 CH30 174 (solidifies)

J

Table IV-D

31

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U9343

X

5 y n Jjl—

/ Q \ -S02NHCNH - ^ / 'N

N_ ^ Z

10 X Z Mp. in ° C

Cl Cl CH3 CH3 130-140

Cl Cl CH3 CH30 182-184

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

Cl CH3 CH3 CH3 188-189

Cl CH3 CH3 CH30 187

Cl CH3 CH30 CH30 148-151 20 CH30 Cl CH30 CH30 178

Table IV-E 25 o N / x R5- / ~ θ \ -SO-NHCNH- / \

MT

30 R

R? R 2 X Z Mp. in ° C

Cl Cl CH30 CH30 182-190 CH30 CH30 CH30 CH30 218-219 NO- Cl CH, 0 CH- 163-164 35 1 j j

Table IV-F

32 149343

ISLAND

r® O X

\ - S N— ^

5 / Q \ -S02NHCNH - // xN

V ^^ 2

R ^ _ X Z Snip, i ° C

10 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 15 CH3 CH3 CH3 CH30 160-163 CH3 CH3 CH30 CH30 169-173 CH-, 0 Cl CH, CH-, 0 174-179 3 3 3 CH30 Cl CH30 CH30 165 CH30 Cl CH3CH20 CH3 183- 183.5 20 CH30 F CH30 CH30 201-203 FF CH3 CH3 164-165 FF CH30 CH30 206-208

Cl CH30 CH3 CH30 176 ci ch3o ch3o ch3o 201 Cl CF3 CH3 CHsO 177-178

Cl CF3 CH30 CH30 165-167

Cl H CH30 CH3 110-112 salt with CL 2 COO

Cl H CH30 CH3 oil (CH3CH2CH2CH2) 4N + salt

Cl H CH30 CH3 oil [CH3 (CH2) g] 4N + salt Cl1 NO2 CH3 CH3

Cl N02 CH30 CH30 168-174 CH30 CH3 CHsO CH30 210-213 F CH3 CH3 CH3 180-182 F CH3 CH3 CH30 185-186 35 33 149343

ISLAND

R3 R6 X Z Mp. in ° C

F CH3 CH30 CH30 191-192 CH3 F CH3 CH3 201-205 CH3 F CH30 CH30 183-184 5 CELjS Cl CH3 CH30 95-100 CH3S Cl CH30 CH30 190-194 CH3 N02 CH3 CH30 190-191 CH3 N02 CH3 CH30 190-230 (decomposition) Na salt CH3 NO2 CH30 CH30 142-145 10 CH3 (CH3) 2CH CH3 CH3 167 CH3 (CH3) 2CH CH3 CH30 115 CH3 (CH3) 2CH CH30 CH30 135 CH3CH20 Cl CH3 CH30 179-181 CH3CH20 CH3CH20 CH3 CH3 134- 136 CH, CH90 CH, CH90 CH.O CH30 187-188 CH3 Cl CH3 CH3 189-191

Br Br CH3 CH3 204-205

Br Br CH3 CH30 178-180

Br Br CH3 ° CH3 ° over 275 20 CH30 CH30 CH3 CH3 144-150 CHgO CH30 CH3 CH30 187-205 (decomposition) CH30 CH30 CH30 CH30 oil (CH3CH2CH2CH2) 4N + salt CH30 CH30 CH30 CH30 187-188 CH30 CH30 CH3CH20 CH3 96-100 CH30 CH30 CH3CH20 CH30 138-141 (CH3) 2CH (CH3) 2CH CH30 CH30 123-128 CH, CHOO Cl CH O CH ^ O 174-178 3 2 3 -J 1 35

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Table IV-G

34 149343

/ R? O X

5 / n \ "SO-NHCNH-VH7 3 2 N = <

XR XZ

r7 X Z Mp. in ° C

10

Cl Cl CH3 CH3 142-158

Cl Cl CH3 CH30 203-206

Cl Cl CH30 CH30 205-208

Cl CH3 CH3 CH30 171-172 15 Cl CH3 CH30 CH30 173-176 F F CH3 CH3 192-193 F F CH3 CH30 213-215 F F CH30 CH30 275 20

Table IV-H

* 1 _ O N_ / X

R4 R6 X Z Mp. in ° C

30 Cl Cl CH3 CH3 210-213

Cl Cl CH30 CH30 207 35 35

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U93Å3

Table IV-I O M ^ 5 r5- / q ^ -so2nhcnh - ^ = 1i

10 R 2 X Z Mp. in ° C

Cl Cl CH3 CH3 194-195

Cl Cl CH3 CH30 188-190

Cl Cl CH30 CH30 280 NO2 CH30 CH3 CH30 182-185 15

Table IV-J 0 N_ ^ X

R 5 - / - O -SO-NHCNH- / N

4ΛΗ 3 N- <Z

R R

3 4 5 o

R R R X Z Mp. i C

25

Cl Cl Cl CH3 CH3 178-184

Cl Cl Cl CH3 CH30 169-171

Cl Cl Cl CH30 CH30 175-178 1 35

Table IV-K

36 o 149343

R \ _ 0 N _ </ X

/ ^ - SO ^ HCHH- ^ N

\ \ 3 Z

R R

R3 R4 R6 X Z Mp. in ° C

CH3 CH3 NO2 CH3 CH30 182-184 (decomposition) CH3 CH3 NO2 CH3 CH3 196-197 (decomposition)

Table IV-L 15

R7 _ X

i- * '° / qX-so ^ hcnh-, a

a '\ 3 R4 R

20

R ^ R ^ R ^ X Z Mp. in ° C

CH3 Cl Cl CH3 CH3 168-170 CH3 Cl Cl CH30 CH3 176-178 CH30 Cl Cl ch3 ° CH30 173-175 25

Table IV-M

r6 O / X

v "N / R5- ^ Qy -SQ2NHCNH - ^^ N 30 '\ r3 - ^ z

R ^ R ^ R ^ X Z Mp. in ° C

Cl Cl Cl CH3 CH3 184-186

Cl Cl Cl CH3 CH30 169-171 35 Cl Cl Cl CH30 CH30 165-168 CH30 Cl CH30 CH30 CH30 195

ISLAND

37 149343

Table IV-N 7

R O X

R5 / island ^ -S02NHCNH-

5 '' 'R3 ^ Z

R ^ R ^ R ^ X Z Mp. + 1 ° C

CH3 CH3 CH3 CH3 CH3 205-207 CH3 CH3 CH3 CH3 CH30 177-186 10 CH3 CH3 CH3 CH30 CH30 160-167 F F F CH3 CH3 163-169 F F CH CH3 CH30 152-155 F F CH30 CH30 194-196

Cl Cl Cl CH3 CH3 188-190 15 Cl Cl Cl CH3 CH30 159-161

Cl Cl Cl CH30 CH30 166-168

Table IV-0

20 r6 \ R? ISLAND

> OJ-SO2NHCNH- ^ R4 R3

25 R ^ R ^ X Z Mp. in ° C

CH3 CH3 CH3 CH3 CH3 CH3 200-205 CH3 CH3 CH3 CH3 CH3 CH30 195-197 CH3 CH3 CH3 CH3 CH30 CH30 185-189

Cl Cl Cl Cl CH3 CH30 187 30 Cl Cl Cl Cl CH30 CH30 250

Example 12 N - [(4-Methoxy-6-methyl-1,3,5-triazin-2-yl) aminocarbonyl] -2-thiophenesulfonamide To a suspension of 14.0 g of 2-amino-4-methoxyphenyl 6-Methyl-1,3,5-triazine in 300 ml of acetonitrile is added dropwise to thiophene-2-sulfonylisocyanate. After stirring for 6 hours, the mixture is filtered to give the desired solid, m.p. 182-184 ° C.

By analogy to the procedure described in Example 12 and using equivalent amounts of the appropriate amino-1,3,5-triazine derivative and sulfonyl isocyanate, the compounds listed below in Table V can be prepared.

Table V-A

10 0 II N · M ·· ^

, -.- SO-NH-C-NH- / SN

XX H

R9 V °

_ R9 R ^ X Z Mp. in ° C

Cl Cl CH3 CH3 127-133 20 Cl Cl CH3 CH30 165-171

Cl Cl CH30 CH30 181-184

Table V-B 25

_ O X

fj H „N /

L] S00NHCNH- (/ VN

2 V = / R8 2 30 8

R X Z Q Mp. in ° C

H CH3 CH3 S 174-176 H CH3 CH30 S 182-184 H CH30 CH30 S 191-192 35 Cl CH3 CH3 S 192-195

Cl CH30 CH30 S 193-195 H CH3CH2 CH3 S 132-138 H CH3S CH3 S 223-225

ISLAND

39 149343

Example 13 N - [(4,6-Dimethoxy-1,3,5-triazin-2-yl) aminocarbonyl] -1- -naphthalenesulfonamide

To a suspension of 16 g of 2-amino-4,6-dimethoxy-1,3,5-5-triazine in 400 ml of acetonitrile is added dropwise with stirring 23.3 g of 1-naphthalenesulfonylisocyanate. The mixture is stirred for 14 hours and the resulting solid product is filtered off. After washing with ethyl ether, the product has m.p. 171-172 ° C.

Analogous to the procedure 10 described in Example 13 and using equivalent amounts of the appropriate amino-1,3,5-triazine and sulfonyl isocyanate, the compounds listed in Table VI can be prepared below.

Table VI 15

SO-NHCNH-A Y

yv I W

20 z 20

X Z Mp. in ° C

CH3 CH3 179-183 CH3 CH30 186-188 25 CH30 CH30 171-172

Example 14 N - [(4,6-Dimethoxy-1,3,5-triazin-2-yl) aminothioxomethyl] -benzenesulfonamide A mixture of 20 g of benzenesulfonylisothiocyanate, 15.6 g of 2-amino-4,6-dimethoxy -1, 3,5-triazine, 250 ml of acetonitrile and a catalytic amount of dibutyltin dilaurate are stirred for 24 hours. After filtration to remove unreacted triazine, the acetonitrile is evaporated to give a gummy residue.

35 Trituration of this material with ethyl ether precipitates the desired product, which is isolated by filtration, m.p. 148-150 ° C.

40 0 149343

By analogy to the procedure described in Example 14 with an equivalent amount of the appropriate sulfonyl isothiocyanate and aminotriazine, the compounds listed below in Table VII can be prepared.

5

Table VII S

r1so2nhcnhr2 10

R ~ * ~ R2 m.p. in ° C

y- N- ^ ° CH3 // λ- - {/ y 182-185

NIL ^ AND,

15 J

/ CH 3

Qn-S J

-ζΤΪ 142-144

CH3 ^ CH

20 s CH3? 0 ° η3 (? - (/% 188-190 \ - / n. = / (Decomposition)) AND, 0CH3

25 J

Useful compositions containing the compounds of formula I can be prepared in a conventional manner. These compositions include powders, granules, pellets, solutions, suspensions, emulsions, moisturizers, emulsifiable concentrates and the like. Many of these can be used directly. Spray preparations can be stretched in appropriate media and used in spray volumes of a few liters to several hundred liters per liter. acres. Highly concentrated preparations are primarily used as intermediates for further formulation. The preparations contain substantially approx. 0.1 to 99% by weight of active ingredient and at least one ingredient selected from (a) ca. 0.1 to 20% surfactant and (b) approx. 1-99.9% solid or liquid diluent.

Usually the compositions contain these ingredients in the approximate amounts listed in the following 10 10 20 20 30 30 42 42 149343 • μ> Η • μ

X

ta <ΰ

D

Π3! _J ^ ι ++ <D ο mo m µ Ό Η η cm m η cm <u ro i i i i i t i

> · Η ι-H OHOO O

0 g • cn S '-Η σι 1.3 "_ G η in σι σι ο> 4 (1) i" m to m οι i-i

+ 1¾ I I I I I I I

μ rø o oooin o 0 · Η ^ * 3 <Γ- ~ 1¾ g «—I 0) 'ϋ w Ό h Go ο o in m σι η> ιοσι in m cm σι σι

> · Η -µ I I I I I I

+> w o moHH o H X CD · CM H - σι α) <Λ Ο Λ (0 Eh

rH CD

g μ «i g ta μ -μ« cD μ Λ CD <D μ φ μ G η cu * CP CD Ο Η μ G D> -η cd α) (ϋ -Η Η ω Ρι Ό

G G G £ <D

0 w g ^ CD CP µ

CD -rl ^ CD μ Di O <D

µ w h cd ω µ cd cftcD-µ s µ-µ

> CD 0> G CO CD G

ι-H Dl Ή μ 4-> CD

D «mod 11 ID id O h Οι g μ gg di μ η g cd CD MCDHCD-H CD G 0 +> 4J ID GDC Ο Φ Ό CM (0 di-hogg so ιβ ή μ GH-H-Ho gg μ ' θ. g

Pi O CD - X> 111 CD 55 Oi

ISLAND

43 149343

Of course, lower or higher concentration of active ingredient may be used depending on the intended use and the physical properties of the compound. It is sometimes desirable with greater amounts of surfactant 5 relative to active ingredient, and this is achieved by incorporation into the composition or by tank mixing.

Typical solid diluents are described in Watkins et al., "Handbook of Insecticide Dust Diluents and Carriers," 2nd Edition, Dorland Books, Caldwell, New Jersey.

10 The more absorbent diluents are preferred for moisturizers and heavier for powders. Typical liquid diluents and solvents are described in Mardsden, "Solvent's Guide," 2nd Edition ^ Intersicience, New York, 1950. Solubility below 0.1% is preferred for suspension concentrates and solvent concentrates are preferably stable against phase separation at 0 ° C. . An overview of surfactants and recommended uses is given in "McCutcheon's Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood, New Jersey, and in Sisely and Wood, "Encyclopedia of 20 Surface Active Agents," Chemical Publ. Co., Inc. New York, 1964. All compositions may contain minor amounts of additives to reduce foam, cake formation, corrosion, microbiological growth, and the like.

The methods of preparing such compositions are well known. Solutions are prepared by simple mixing of the ingredients. Finely divided solid compositions are prepared by mixing and usually milling in a hammer mill or liquid energy mill. Suspensions are prepared by wet milling, cf. eg. the process described in U.S. Patent No. 3,060,084. Granules and pellets can be prepared by spraying the active material onto preformed granular carriers or by agglomeration. Cf.. JE Browning, "Agglomeration", Chemical Engineering, Dec. 4, 1967, page 147ff, and "Perry's Chemical Engineer's Handbook," 4th Edition, 35 McGraw-Hill, New York, 1963, pages 8-59ff.

149343 44 i i> o i

For further information on the technique of preparation of compositions, reference may be made, for example, to U.S. Patent No. 3,235,361, column 6, line 16 to column 7, line 19, and examples 10-41, described in U.S. Pat. U.S. Patent No. 3,309,192, 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, disclosed in ± 1 to U.S. Patent No. 2,891,855, column 3, line 66 to column 5, line 17, and Examples 1-4, GC Klingman, "Weed 10 Control as a Science," John Wiley & Sons, Inc., New York, 1961, pages 81-96 and J.D. Fryer and S.A. Evans, "Weed Control Handbook", 5th Edition, Blackwell Scientific Publications, Oxford, 1968, pages 101-103.

In the following examples, all parts are by weight, unless otherwise stated.

Example 15 Moisturizing Powder N - [(4,6-Dimethylpyrimidin-2-yl) aminoO-2Q carbonyl] benzenesulfonamide 80%

Sodium alkyl naphthalenesulfonate 2%

Sodium lignin sulfonate 2%

Synthetic amorphous silica 3%

Kaolinite 13% 25 Ingredients are mixed, ground in a hammer mill, until all solids are substantially less than 50 microns in size and then re-mixed.

Example 16 Moisturizing Powder 3Q N - [(4-methoxy-6-methylpyrimidin-2-yl) aminocarbonyl] -2-chloro-5-methoxybenzenesulfonamide 50%

Sodium alkyl naphthalenesulfonate 2%

Low viscous methyl cellulose 2%

Diatomaceous earth 46% 35 The ingredients are mixed, coarsely ground in a hammer mill and then ground in an air mill to form particles

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45 149363 of active substance having a diameter of substantially less than 10 µm. The product is remixed before packaging.

Example 17

granules

Powder Powder of Example 16 5%

Attapulgite granules (0.84-0.42 mm) 95%

A slurry of the moisture powder containing about 10% solids is sprayed onto the surface of the attapulgite granule in a double cone mixer. The granulate is dried and packaged.

Example 18 Extruded Pellets N - [(4-Methoxy-6-methylpyrimidin-2-yl) -aminocarbonyl] -2-chlorobenzenesulfonamide 25%

Anhydrous sodium sulfate 10% Crude calcium lignin sulfonate 5% 20

Sodium alkyl naphthalenesulfonate 1%

Calcium / magnesium bentonite 59%

The ingredients are mixed, ground in a hammer mill and moistened with approx. 12% water. The mixture is extruded as cylinders 25 having a diameter of approx. 3 mm which is cut to form pellets with a length of approx. 3 mm. These can be used directly after drying or the dried pellets can be crushed so that the material passes a sieve with a mesh width of 0.84 mm. The granules which are retained on a sieve with a mesh opening of 0.42 mm can be packaged for use and the finer particles recycled.

35

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46 149343

Example 19 Oil suspension N- [(4,6-dimethoxypyrimidin-2-yl) aminocarbonyl] -2,5-dichlorobenzenesulfonamide 25% g Polyoxyethylene sorbitol hexaoleate 5% High aliphatic hydrocarbon oil 70%

The ingredients are ground in a sand grinder until the solid particles have a size of less than approx. 5 jam. The resulting suspension can be used directly, but preferably after 10 stretching with oils or emulsifying in water.

Example 20 Moisturizing Powder N - [(4,6-Dimethylpyrimidin-2-yl) -amino-carbonyl] -2,6-dichlorobenzenesulfonamide 20%.

Sodium alkyl naphthalenesulfonate 4%

Sodium lignin sulfonate 4%

Low viscous methyl cellulose 3%

Attapulgit 69% 20

The ingredients are mixed thoroughly. After milling in a hammer mill to form particles substantially less than 100 µm, the material is re-mixed and sieved through a 0.3 mm mesh screen, after which the product is packaged.

Example 21

Low-strength granular N-t (4-methoxy-6-methylpyrimidin-2-yl) -aminocarbonyl] -2-methylbenzenesulfonamide 1% N, N-dimethylformamide 9%

Attapulgite granules (0.84-0.42 mm) 90%

The active ingredients are dissolved in the solvent and the solution is sprayed onto dust-free granules in a double-cone mixer. After spraying of the solution is completed, the mixing apparatus is started for a short period of time, after which the granulate is packaged.

Example 22 Aqueous suspension of N- [(4,6-dimethylpyrimidin-2-yl) -aminocarbonyl] -benzenesulfonamide 40%

Polyacrylic Acid Thickener 0.3%

Dodecylphenol polyethylene glycol ether 0.5% Disodium phosphate 1%

0.5% monosodium phosphate

Polyvinyl alcohol 1.0%

Water 56.7% 15 The ingredients are mixed and ground in a sand mill to form particles which are substantially less than 5 µm.

Example 23 Solution N - [(4-methoxy-6-methylpyrimidin-2-yl) amino carbonyl] -2-chlorobenzenesulfonamide - sodium salt 5%

Water · 95%

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

Example 24

Low Strength Granules 30 - N-t (4,6-Dimethylpyrimidin-2-yl) -aminocarbonyl] -2,6-dichlorobenzenesulfonamide 0.1%

Attapulgite granules (0.84-0.42 mm) 99.9%

The active ingredient is dissolved in a solvent and the solution is sprayed onto the dust-free granule in a double cone mixer. After spraying the solution is 0.

48 149343, the solvent is heated to evaporate the solvent. The material is left to cool and then packaged.

Example 25

Granulate N - [(4,6-dimethoxypyrimidin-2-yl) -aminocarbonyl] -2,5-dichlorobenzenesulfonamide 80%

Wetting agent 1% 10 Raw lignin sulfonate salt (containing 5-20% of the natural sugars) 10%

Attapulgitler 9%

The ingredients are mixed and ground to pass a 100 mesh screen. This material is then added to a fluid bed granulator where the air flow is adjusted to gently fluidize the material and a fine mist of water is sprayed onto the fluidized material. The fluidization and spraying is continued until the granulate of the desired size is formed. Spraying is interrupted, but fluidization 20 is maintained, optionally during heat application, until the water content is reduced to the desired level, usually below 1%. Then, the material is taken out, sieved to the desired size range, usually 1410-149 µm, and packaged for use.

25

Example 26 High Concentrated Preparation N - [(4,6-Dimethylpyrimidin-2-yl) -aminocarbonyl] -2-thiophenesulfonamide 99% Silica aerogel 0.5%

Synthetic amorphous silica 0.5%

The components are blended and ground in a hammer mill to form a material which substantially passes a sieve with a sieve opening of 0.3 mm. The concentrate can be formulated more evenly if necessary.

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49 149343

Example 27 Moist powder N-t (4-methoxy-6-methylpyrimidin-2-yl) -amino-carbonyl] -2-chlorobenzenesulfonamide 95% g Dioctyl sodium sulfosuccinate 0.1%

Synthetic fine powder silica 4.9%

The ingredients are mixed and ground on a hammer mill to form particles substantially less than 100 µm. The material is sieved through a US sieve 50, 10 and then packaged.

Example 28 Moisturizing Powder N - [(4-Dimethoxypyrimidin-2-yl) -aminocarbonyl] -2,5-dichlorobenzenesulfonamide 40%

Sodium lignin sulfonate 20%

Montmorillonitler 40%

The ingredients are thoroughly mixed, ground coarsely in a hammer mill and then in an air mill to form particles substantially less than 10 µm. The material 20 is then re-mixed and packaged.

Example 29 Oil Suspension N - [(4-Methoxy-6-methylpyrimidin-2-yl) -amino-carbonyl] -2-methylbenzenesulfonamide 35%

Mixture of polyol carboxylic acid esters and oil-soluble petroleum sulfonates 6%

Xylene 59%

The ingredients are mixed and ground in a sand mill to form particles substantially less than 5 microns. The product can be used directly, stretched with oils or emulsified in water.

35

5Q

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149343

Example 30 Moisturizing Powder N - [(4,6-Dimethoxy-1,3,5-triazin-2-yl) aminocarbonyl] benzenesulfonamide 80%

Sodium alkyl naphthalenesulfonate 2% 5

Sodium lignin sulfonate 2%

Synthetic amorphous silica 3%

Kaolinite 13%

The ingredients are mixed, ground in a hammer mill until the solid has a size of substantially less than 50 µm, after which it is re-mixed and packaged.

Example 31 Moist Powder N - [(4,6-Dimethyl-1,3,5-triazin-2-yl) -aminocarbonyl] benzenesulfonamide 50%

Sodium alkyl naphthalenesulfonate 2%

Low viscous methyl cellulose 2%

Diatomaceous earth 46%

The ingredients are mixed, coarsely ground in a hammer mill, and then milled in an air mill to form particles having a diameter of substantially less than 10 µm. The product is remixed before packaging.

Example 32 Granules

Moisturizing Powder of Example 31 5%

Attapulgite granules (0.84-0.42 mm) 95%

A slurry of the moisture powder containing approximately 25% solids is sprayed onto the surface of the attapulgite granulate 30 in a double cone mixer. The granulate is dried and packaged.

35 o 51 149343

Example 33 Extruded Pellets N - [(4-Methoxy-6-methyl-1,3,5-triazin-2-yl) -aminocarbonyl] -2-chlorobenzenesulfonamide 25%

Anhydrous sodium sulfate 10% 5 Crude calcium lignin sulfonate 5%

Sodium alkyl naphthalenesulfonate 1%

Calcium / magnesium bentonite 59%

The ingredients are mixed, ground in a hammer mill and then moistened with approx. 12% water. The mixture is extruded in the form of cylinders having a diameter of approx. 3 mm, which is then cut to form pellets having a length of approx. 3 mm.

These can be used directly after drying or the dried pellets can be crushed so that the product passes a sieve with a mesh width of 0.84 mm. The granulate, which is retained on a sieve of mesh size 0.42 mm, can be packaged for use and the fine particles recycled.

Example 34 Oil Suspension 20 N - [(4,6-Dimethoxy-1,3,5-triazin-2-yl) -amino carbonyl 1-2-chloro-5-methoxybenzenesulfonamide 25%

Polyoxyethylene sorbitol hexa oleate 5% High aliphatic hydrocarbon oil 70%

The ingredients are ground in a sand grinder until the solid 25 particles have a size of less than approx. 5 pm The resulting suspension can be used directly, but preferably after stretching with oils or emulsifying in water.

Example 35 Moisturizing Powder 3 ° N - [(4,6-Dimethoxy-1,3,5-triazin-2-yl) -aminocarbonyl] -2-chlorobenzenesulfonamide 20%

Sodium alkyl naphthalenesulfonate 4%

Sodium lignin sulfonate 4%

Low viscous methyl cellulose 3% Attapulgit 69% o 52 149343

The ingredients are mixed thoroughly. After grinding in a hammer mill to form particles having substantially a size less than 100 µm, the material is re-mixed and sieved through a screen having a mesh opening of 0.3 mm, upon which the product is packaged.

Example 36 Oil Suspension N - [(4,6-Dimethoxy-1,3,5-triazin-2-yl) -amino-carbonyl] -benzenesulfonamide 35%

Mixture of polyol carboxylic acid esters and oil-soluble petroleum sulfonates 6%

Xylene 59%

The ingredients are combined and ground in a sand mill - to form particles with a size substantially below 3 microns. The product can be used directly, stretched with oils or emulsified in water.

Example 37 2Q High Concentrated Preparation N - [(4,6-Dimethoxy-1,3,5-triazin-2-yl) -amino-carbonyl] benzenesulfonamide 99%

0.5% silica gel

Synthetic amorphous silica 0.5%

The components are mixed and ground on a hammer mill 25 to form a material which substantially passes a sieve with a mesh opening of 0.3 mm. The concentrate can be further formulated if necessary.

Example 38 30

Low Strength Granules N - [(4-Methoxy-6-methyl-1,3,5-triazin-2-yl) -aminocarbonyl] -2-chloro-5-methoxybenzenesulfonamide 1% Ν, Ν-dimethylformamide 9 % 35 Attapulgite granules (0.84-0.42 mm) 90%

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53 149343

The active ingredient is dissolved in the solvent and the solution is sprayed onto dust-free granules in a rotary mixing apparatus. After spraying of the solution is complete, the mixer runs for a short time, after which the granulate is packaged.

Example 39 Aqueous suspension N - [(4,6-dimethyl-1,3,5-triazin-2-yl) -amino-carbonyl] -benzenesulfonamide 40%

Polyacrylic Acid Thickener 0.3%

Dodecylphenol polyethylene glycol ether 0.5%

Disodium phosphate 1%

Monosodium phosphate 0.5% Polyvinyl alcohol 1.0%

Water 56.7%

The ingredients are mixed and ground in a sand mill to form particles having substantially a size of less than 5 µm.

20

Example 40 Solution N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) aminocarbonyl] -2-chlorobenzenesulfonamide - sodium salt 5% Water 95%

The salt is added directly to the water with stirring to form the solution which can then be packaged for use. 1 35

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54 149343

Example 41 Granulate N - [(4,6-dimethoxy-1,3,5-triazin-2-yl) aminocarbonyl] -2,5-dimethoxybenzenesulfonamide 80% Wetting agent 1% Raw lignin sulfonate salt containing 5-20% of the natural sugars 10%

Atta Pulgitler 9%

The components are mixed and ground to pass a 100 mesh screen. This material is then added to a fluid bed granulation apparatus where the air flow is adjusted to gently fluidize the material and a fine spray of water is sprayed onto the fluidized material. Fluidization and spraying are continued until granules of the desired size are formed. The spraying is then interrupted, but the fluidization is continued, optionally with heating, until the water content is reduced to the desired level, usually less than 1%. The material is then removed, sieved to the desired size range, usually 1410-149 µm and packaged for use.

20

Example 42 Low Strength Granules N - [(4-Methoxy-6-methyl-1,3,5-triazin-2-yl) -aminocarbonyl] -2-chlorobenzenesulfonamide 0.1% Attapulgite granulate (0.84-0.42 mm 99.9%

The active ingredient is dissolved in a solvent and the solution is sprayed onto dust-free granules in a double cone mixer. After spraying of the solution is complete, the material is heated to evaporate the solvent. The material is left to cool and then packaged.

35

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55 149343

Example 43 Moist powder N- [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) aminocarbonyl] -2-chloro-5-methoxybenzenesulfonamide 95% Dioctyl sodium sulfosuccinate 0.1%

Synthetic fine powder silica 4.9%

The ingredients are mixed and ground on a hammer mill to form particles of substantially less than 100 µm. The material is sieved through a US 10 sieve No. 50, after which it is packaged.

Example 44 Moisturizing Powder N - [(4-methoxy-6-methyl-1,3,5-triazin-2-15-yl) aminocarbonyl] -2-chlorobenzene sulfonamide 40%

Sodium lignin sulfonate 20%

Montmorillonitler 40%

The ingredients are thoroughly mixed, coarsely milled on a hammer mill and then on an air mill to form pairs of ticks having a size of less than 10 pti. The material is then re-mixed and packaged;

The compounds of formula I can be formulated using the procedures set forth in Examples 15-44.

2g The compounds of formula I are useful as herbicides, they can be used either pre- or post-emergence to control undesirable vegetation in areas without crops and for selective weed control in certain crops, e.g. wheat. Some of these compounds can be used for pre-30 and / or post-emergence control of cypress crops in crops such as cotton, maize and rice. By properly selecting the amount and time of application, the compounds of the invention can be used to favorably modify plant growth.

The exact amount of the compound of formula I, 35 to be used in a given situation will vary depending on the intended end result, the use involved.

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crop, the type of weed to be controlled, the soil type, the composition and method of application, the weather conditions and similar factors. Since so many variables have an influence, it is not possible to specify a range of uses which is suitable in all 5 situations. Broadly speaking, the compound herein is used

looks in quantities of approx. 0.005 to 20 kg / ha, preferably 0.01-10 kg / ha. The smaller amounts in this range are usually selected on light soils, for selective weed control in crops or in situations where maximum effect 10 is not required. Some of the compounds of formula I

may be used in very small amounts for plant growth modification, but larger amounts may also be applicable, depending on factors such as the crop concerned and the time of treatment.

The compounds of formula I can be combined with other herbicidal compounds and are particularly useful in combination with 3- (3,4-dichlorophenyl) -1,1-dimethylurea, the triazines such as 2-chloro-4- (ethylamino) -6- (isopropylamino) ) -s-triazine, the uracils such as 5-bromo-3-sec-butyl-6-methyluracil, N- (phosphonomethyl) glycine, 3-cyclohexyl-1-methyl-6-dimethylamino-s-triazine-2, 4 (1H, 3H) -dione, N, N-dimethyl-2,2-diphenylacetamide, 2,4-dichlorophenoxyacetic acid and closely related compounds, 4-chloro-2-butynyl-3-chlorophenylcarbamate ("Carbyni 1), diisopropylthiolcarbamic acid ester of 2,3-dichloroallyl alcohol ("AvadejP") y diisopropylthiolcarbamic acid, S- (2,3,3-trichloroallyl) ester ("Avadej ^ BW), ethyl-N-benzoyl-N- (3,4-dichlorophenyl) -2-aminopropionate ("Suffix®"), 1,2-dimethyl-3,5-diphenylpyrazolium methylsulfate ("Avengi®"), methyl 2- [4- (2,4-dichlorophenoxy) phenoxy] propionate ("Hoelii"), 4-amino-6-tert.butyl-3- (methylthio) -1,2,4-triazine-5 (4H) -one ("Lexone" ), 3- (3,4-dichlorophenyl) -1-methox yl-methylurea ("Lorox"), 3-isopropyl-1H-1,2,1,3-benzothiadiazine- (4) -3H-one-2,2-dioxide, α, α, α-trifluoro-2, 6-dinitro-N, N-dipropyl-p-toluidine, 1,1'-dimethyl--4,4'-bipyridinium ion monosodium methanarsonate, 2-chloro-2 ', e'-diethylimethoxymethyljacetanilide and 1.1 -dimethyl-3- (α, α, α-trifluoro-m-tolyl) urea ("Cotorari").

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57 149343

The effect of these compounds is described in more detail in the greenhouse experiments below. The experiment is described in detail and the results obtained are stated in connection therewith.

5 Flax seeds (Digitaria sp.), Male spores (Eschi-nochloa crusgalli), oats (Avena fatua), Cassia tora, Ipomoea sp., Bread seeds (Xanthium sp.) in a growth medium and treated preemergence with the test compounds dissolved in a non-phytotoxic solvent. At the same time, cotton plants are sprayed with four leaves (including the gum leaves), creeping beans with the third three-leaf leaf unfolded, finger axis with two leaves, male groove with two leaves, flying oats with one leaf, cassia with three leaves (including the gum leaves), 15 Ipomoea with four leaves (inclusive the seedlings), four-seeded bread seeds (including the seedlings), three-leaf sorghum, three-leaf corn, two-seeded soybean, two-leaf rice, one-leaf wheat, and three-five-leaf cyperus. The treated plants and control plants are kept in a greenhouse 20 for 16 days, after which all plant species are compared with control plants and visual assessment is made for response to the treatment.

The effect of the test compounds tested by this method is given in the following Table IX.

The plant response is expressed as follows: 0 = no effect & or 10 = maximum effect B = staining 30 C = chlorosis or necrosis D = defoliation E = emergence inhibition 6F = delayed flowering G = growth retardation 35

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o 182 149363

The use of the compounds for selective weed control in wheat is illustrated in the four greenhouse experiments below (tests A, B, C and D).

Test A

Two flat plastic onion trays with a diameter of 25 cm are filled with the fertilizer and lime-treated Fallsington sandy clay soil. A tray is sown with corn, sorghum and various grasses. The second tray is sown with soybean, Cyperus ro-10 tundus and various broadleaf weeds. The following grass weed species and broadleaf weed species are used Fingeraks (Digitaria sanguinalis), male spores (Echinochloa crusgalli), flying oats (Avena fatua), Sorghum tail brush, Setaria faberii,

Poa pratensis, Bromus secalinus, Brassica arvensis, Xanthium pennsylvanicum, Amaranthus retroflexus, Aeschynomene virginica,

Ipomoea hederacea, Cassia tora, Sida spinosa, Abutilon theophra path and Datura stramonium. In addition, two cardboard cups with a diameter of 12.5 cm are filled with treated soil. One is sown with rice and wheat, and the other with sugar beet. The four containers are treated pre-merger, ie. the compounds are sprayed onto the soil surface before germination of the seeds.

28 days after treatment, the plants are evaluated. The results obtained are summarized in Table X. It should be noted that wheat has a greater tolerance to the test compounds than most of the weed species. 1 35 183 U9343 sc os ο ο aoatcaxirns ο a ο a ο ο ο ago ago c-cd cd h cd cd σι Η m øpaAH ο $ ^ Ο - § Ο $ 8 $ # ο aaa «.ο aa« · ο ο STH co co o oo o <d <dg 5 (¾ t-

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Test B

25 cm diameter plastic pots filled with Fallsington sandy clay soil are planted with soybean, cotton, alfalfa, maize, rice, wheat, sorghum, Abutilon theophra-5 path, Sesbania exaltata, Cassia tora, Ipomoea sp., Datura stramonium, Xanthium penns , Digitaria sp., Cyperus rotundus, Echinochloa crusgalli, Setaria faberii and Avena fatua. Ca. About 2 1/2 weeks after planting, the young plants and the surrounding soil are sprayed everywhere with the test compound dissolved in a non-phytotoxic solvent. 14 days after treatment, all plants are compared to untreated control plants and visual assessment is done for response to treatment. The results are given in the following Table XI.

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192 149343

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The compounds are used in a non-phytotoxic solvent in the form of total post-emergence sprays of wheat plantings (height 11 cm, 2 leaf stage), 5 oats (Aveha fatua, height 9 cm, 1 leaf stage), Bromus tectorum (height 5 cm, 1-leaf stage), Bromus secalinus (height 5 cm, 1-leaf stage), Alopecurus myosuroides (height 3 cm, 1-leaf stage), and Lolium multiflorum (height 8 cm, 1-leaf stage), and preemergent spraying of sowings with the same plants. All plantings and sowings are made in soil trays with a diameter of 25 cm. The tests are carried out in a greenhouse and the plant response assessment is done 5 weeks after application. The results are set out in the following Table XII.

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The compounds are applied in a non-phytotoxic solvent in the form of total sprays of established (postemergent) wheat plantings (height 22 cm), fly oats (Avena fatua, height 12 cm), Bromus tectorum (height 3 cm), Bromus secalinus (height 5 cm), barley (height 22 cm),

Kochia scoparia (height 5 cm), Matricaria inodora (height 3 cm), Brassica arvensis (height 7 cm), Eupatorium capilli-folium (height 3 cm) and Polygonum concolvulus (height 6 cm), "• 0 and also spraying of Preemergent seedlings with the same plants, all sown in pots containing soil The test is carried out in a greenhouse and the plant response assessment is made 4 weeks after application The results are given in the following Table XIII.

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0 202 149343 The following experiments illustrate the use of the compounds of the present invention for the control of cypress.

Cyperus tubers (Cyperus rotundus) are planted in pots (5 tubers per pot) at a depth of approx. 2.5 cm in 10 cm pots 5 containing Fallsington sandy clay soil. The test compound is applied in the form of a preemergent soil surface spray, a direct tuber spray, soil incorporation into the upper 2.5 cm soil and postemergent spray on leaves of plants with a height of approx. 8-10 cm. The compounds are dissolved in a suitable solvent and applied at a spray volume of 560 liters / ha. The effect of test compounds on plant growth is assessed visually 4 weeks after treatment. The results are set out in the following Table XIV.

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205 U9343

The following experiments illustrate the utility of the compounds of this invention for selectively combating Cyperus in crops.

Plastic trays with a diameter of 25 cm with 5 polyethylene pieces are filled with Fallsington sandy clay soil and seeds of the following plants are planted at a depth of 2.5 cm in each tray: maize (Zea mays), soybean (Glycine max), rice ( Oryza sativa), cotton (Gossypium hirsutum) and Cyperus tubers (Cyperus rotundus). Each test compound is dissolved in a suitable solvent and applied to pre- and postergens in a spray volume of 560 liters / ha. The plants that are treated post-emergence have a height of from 6-14 cm at the time of treatment.

4 weeks after treatment, visual assessment of the effect of the compounds on plant growth is performed. The results are set out in the following Table XV.

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λ m m m hz. a a

0 1 I I

ft CN CN CN

O O O

m W M M

mi HL H I H

0 „0 0 207 149343

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149343 208

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The following experiment illustrates the use of the compounds of this invention to control certain water weed species.

The compounds are applied in a non-phytotoxic solvent in the form of an overall spray on small ponds containing water hyacinth (Eichornia crassipes), plant height approx.

25-30 cm. The test is carried out in a greenhouse and the plant-sponsored is assessed 4 weeks after application. This experiment illustrates the utility of the compounds of this invention for the control of water weeds. The results are given in the following Table XVI.

15 20 25 1 35

Table XVI

211 149343

Plant Response _ Rating_ Amount of Water _ Compound_kg / ha_hyacinth - / _ \ 0 yN = C%

/ C Λ V-SO ^ -NH-C-NH-C ^ CH 1/32 9G

22 /> W

Cl

/ "~ \ O N, 0-CH, 1/32 9G2C

V (SO) -NH-C-NH-C

Vrv il L 1/16 9C

V v CH3 -

Η3 ° _0ν N- 1/16 9G

^ c-n ^ o AZT \

HCl VC-NH-C-NH-SO 2 - (C) 1/8 9G

SC = N / 2 \ W /

/ \ _ / 1/4 9G4C

H3c 1/2 9G4C

H3COv Cl \ _v

HC C-NH-C-NH-SO- _ / () \ 1/32 9G9C

2-yjy »/ 2 * 3“ v V_

/ 2 9 / z ~ x \ 1/32 9G1C

HC C-NH-C-NH-SO - (()) \: = νχ \ _y 1 / f16 9Glc H3c /

Y CH

S O N-c 'J 1/32 9G

/ V »^^

HC C-SOO “NH-C-NH-C CH

h <? _ Jh ^ 16 9G

Table XVI (continued) 212 149343

Plant response-_ rating_ Quantity Water- _ Compound_kg / ha_hyacinth

CH

o N— C 3 1/32 9G5C

SO -NH-C-NH-C *> HC C nN = C '

HC-CH

H3 <Sc-n o C1 / 7 ^ \ 1/32 9G

HCl VC-NH-C-NH-SO -

nc = n / V ^ v / 1/16 9G2C

H3C '

"" H.CO

H C0N 3 i_ ^ C-N ^ O / ^ - x \

Hc 'C-NH-C-NH-SO, ./ ()> 1/32 9G

SC = N / 2 \ W / H 3 CO 2 and 30 N-Cn

/ V- SO_ -NH-C-NH-C ^^ CH 1/32 9G

CH3 (O

Cl CH3

/ Q \ s02-NH-C-NH- <y ^ -0-αΗ3 l / 32 9G9C

\ _ / N N

^ Cl V

0-CH3

Table XVI (continued) 213 149343

Plant Response _ Rating_ Amount of Water _Connection_kg / ha_ Hyacinth

H CO

H3 COv) -v / c - N O / R

N / NNC-NH-C-NH-SOO - (()> 1/32 & G

2 \ W / H CO / '\ and3 H 00>' »* o- / ~ \

W C-NH-C-NH-SO 2 - / ()) 1/32 8G

VC = N '' U3C-o '' - '- H3C ° n \ -v, c = nn o A-T \

N C-NH-C-NH-SO + - (()> 1/32 & G & C

* C-n '2 \ V / H C "\ och3

Cl

Nx o V- \ 1/32 9G7C

H3C- ° f SC-NH-C-NH-SO2- / Q \ 1/16 9G7C

N N \ _ / SC * 0h3 23.4 149363 o

In addition to the herbicidal action, the compounds of this invention also have beneficial modifying effect on the washing stone of certain plant species. Amounts of application (usually 0.01-1.0 kg / ha) and time of use are selected depending on the plant species to obtain desired effects with minimal phytotoxicity. Both vegetative growth and reproductive growth can be regulated. The following examples illustrate the effect on sugar cane, sorghum, Bahia grass and other grasses. In sugar cane and sorghum a so-called "chemical maturation" is produced, resulting in a greater yield of soluble solids (predominantly sugars).

In many other grass species, these compounds limit growth and seed growth, reducing movement requirements. The compounds are also useful for growth control 15 of tree weeds and leaf weeds.

Example A

Dwarf sugar cane plants with an age of 6-8 months are grown with 3-5 stems per year. cm pot (height 1.5-3 m) and sprayed with the test compound (2 pots per compound). Each stem is measured to the highest visible leaf collar at the start and end of the trial to determine the effect on height growth. When the stalks are harvested 5 weeks after treatment, the juice is extracted from the stalks and the soluble solids are determined in the middle of the upper third, middle third and lower third of each stalk. The results are given in the following Table XVII. The results in Table XVII show that in stems treated with the compounds of this invention, the amount of soluble 30 substances is increased and growth is limited relative to the solvent control plant (500 liters / ha of water plus surfactant "Tween" ® 20 in an amount of 0.2%).

35

O Table XVII

215 149343

Part of cane stem Growth Lower kg / ha (cm) ste_Midten Top

Cl Ρ ° Β3 6 If 1 £ § S: .1 ta3 · _ ^ CH3 0 N-Cl ^ 3 0.25 15 18.1 18.9 13.4 10 U .VsO.-NH-C-NHC CH 1 , 0 6 19.9 20.4 15.8 v_y 2 w NCH3

Solvent Control - 40 16.7 13.8 6.1 OCH, -1.1 O, Ν-c '0.25 3 19.9 20.2 16.8 15 µg / VsOo-NH-C-NHC N 1.0 4 18.8 19.9 16.6

• OCH3 Example B

20 Sugarcane plants are grown with one plant per year. 15 cm pot to a stage just before axis emergence, and the compounds listed below are sprayed. Visual assessment is carried out approx. 3 weeks after spraying. After 4 weeks, the plants are harvested and the content of soluble solids is determined in the center by the upper, middle and lower parts of each stalk. It is apparent from the data set out in Table XVIII that the percentage soluble solids content is increased and growth and flowering are restricted in stems treated with the compounds in question.

30 35

Table XVIII

216 149343

Dissolved solids expressed as% of control values in different parts _ of durable silk 3-week - response rating- Lower _Connection_kg / ha_melt_ste_Midten Top

CEL

0 N-Cy 1.0 9G, F, 2X 114 132 69 / Λ-SO -NHC-NH-C CH 4.0 9G, F 115 128 '-' 'n = c' \ CH3 CH pCH, p JO JSI -C 0.03 9G, F, 3X 119 99 84 / V 50 -NHC-NH-C '' CH 0.5 & G-F-3X 119 119 112

'-' N = C

'0B3

CH

O yN-Cx 1.0 8g, F, 2x 114 140 96

L V SO.-NHC-NH-C 'CH

'-' N = € H

CH

S. O N-c '0.125 & G, F, 1C 119 109 88 HC C-SO.-NH-C-NH-C CH 2.0 & G, F 122 115 66 u 11 Z v /

HC-CH N = C

'CH3

, OCH

QO ^N = C 0.5 9G, F, 2X 111 100 57 SO, -NHC-NH-C CH 2.0 & G, F, 2X 118 105 59

'N-C

cl 'bcH3 CH.

/ 3

/ = Λ 9, N = C

L, VsO, -NHC-NH-C CH 0.5 7G 115 106 98 ^ 2 vc; OCH2CH3 ch3 ch3

Mso -nhc-nh- / ~% h ° '125 9G'F'1C 139 115 140 ^ -S02 NHC NH C ^ CH 0fS 9g, f, 2C 147 129 146 \ CH3, CH / CH3 p6 O NC 0.125 & G , F 113 113 114 - / -SO 2 -NHC-NH-C jCH 0.5 SG, F 120 113 121

) - N = C

CH3 ch3

Table XVIII (continued) 217 149343

Dissolved solids expressed as% of control values in different parts of durastilke_ 3-week response assessment- Lower _Connection_kg / ha measure_ste_Midten Top

F CH

N = C 0.125 & G, F, 1C 127 127 136 (N Λ-SO -NH-C-NH-C CH 0.5 & G, F, 1C 127 127 136

'-' N = C

VCH3 AND, O N-C 0.25 & G, F 120 120 121 L Λ-SO-NHC-NH-C 'CH 1.0 & G, F 120 120 121

- S N = C

• 'CH3

OCH

/ r ^ r \ O N-C 0.25 & G, F 120 113 107 (. Λ-SO-NHC-NH-C '' CH 1.0 & G, F 113 113 107

\ -F N = C

'OCH3

Cl PH 3

O ^ N-C

L N-SO -NHC-NH-C CH 0.5 6G, F, 2X - 122

y— * N = C

C1 CH3 OCH- / -r / OCH3 O ^ N-c '<(Λ-SO-NHC-NH-C CH 0.125 9G, F, 8X - 130 - y1 * n = c

Cl OCH3 pi, CH3

r = \ n N-C

L N-SO.-NHC-NH-C 'CH 0.06 9G, F, 2X - 139

^ 2 W

\

H

Cl / CI3

O / (N-C

L / V 50 O NHC-NH-C CH 0.06 & G, F, 2U - 165 CH3

Cl F / CH3

W O N-C

(\ / V 50 -NHC-NH-CH CH 0.06 & G, F, 1X - 165

'-' N = C

CH3

Table XVIII (continued) 218 149343

Dissolved solids expressed as% of control values in different parts of durra silk 3-week response assessment- Lower-compound_kg / ha measure_ste_Midten Top "-in" OCH_

W O N-C

C / VSO.-NHC-NH-C CH 0.25 0 - 122

'-' N = C

0CH3 / 0CH3 QO N = Cn 0.03 & G, F, 2X 119 112 116 SO -NHC-NH-C £ E 0.125 & G, F, 2X 135 111 105 'NC 0.5 & G, F, 2X 126 117 108 d CH3

OCH

O N - ((0.125 5G, F, 2X 116 107 101 L \ -S0 -NHC-NH-C N 0.5 8G, F 115 107 113 '-' N = C 2.0 8G, F 118 107 113 ° CH3

CH

O N-C 0.125 8G, F, 3x 128 123 118 C VsOp-NHC-NH-C N 0.5 9G, F 143 124 105 N = C 2.0 9G, F 127 111 132

OCH

__ o JS-C 0.125 & G, F, 1C 127 124 125 Λ A-SO ^ -NHC-NH-cf a 0.5 & G, F, 2C 120 113 79 'N = ctf 2.0 & G, F, 2C 133 120 114 ch3 F = delayed flowering 219 149343 o

Example C

Bahia grass plants (Paspalus notatum, Flugge) grown in 13 cm pots are sprayed with the compounds listed below in Table XIX when the seed axes are just ready to break out.

5 The plants have a height of approx. 35 cm and 3 pots are sprayed over the top (560 liters / ha) with each application volume. The results given in the following Table XIX are recorded 45 days after treatment. The compounds of this invention retard growth and suppress seed growth.

10

Table XIX

45-day Percent response suppression · 15 kg7ha judging_of seed ax_ CH_ SO NC 3 ° '03 2G 10 HC C-SO '-NH-C-NH-C CH' 't Τ' '"" 2 W 0.5 3G' 2U 90 HC CH v, H 1.0 3G, 2U 100 20 ^ - / ™ 3 o «Τ '0.008 2g 0 O-S0, -OT-C-NH-C CH 3G 30 VV 2' '0.125 9G, 1C , 2U 95 '0.5 9g, 2C, 2U 95 CH3

OCH

O n = C 3 0.008 2G 70 25 VsO 2 -NH-C-NH-C VCH 0.03 7G 70 \ γ 2 * N_C * 0.125 & G, 2C, 2U 95

Cl 'CH 0.5 & G, 3C, 2U 100 1 35 0 220 149343

The following experiments serve to further illustrate the biological effect of the compounds of this invention. The experiments illustrate the herbicidal action of the compounds with selectivity for two important crop plants, rice and wheat.

The test compound is applied in a non-phytotoxic solvent to soil pots containing seeds of hybrid rice, Japanese rice, Echinochloa crusgalli and Ipomoea sp. A compound is also applied to wheat, Avena fatua, Bromus teactorum and Bromus secalinus. Established plantings (post-10 emergence) of some or all of the above plants are also included in the experiment. The plants are kept in greenhouses and visual plant response assessment is carried out approx. 3 weeks after application. The results are given in the following Table XX.

15 20 25 1 35 149343 221

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Claims (4)

149343 O Patent Claims. 1. Sulfonamide derivatives with herbicide and plant growth regulating effect, characterized in that they have the general formula 5; R1-SO2-NH-C-NH-R where R is 10. X N— (N— / _ {/ Λ or 'ft Z ^ Z R1 is R1 R2 3 -Q-r5 / Λ / A or 00 ' R 4 and R 5 R 6 R 7 R 8 6 2 R and R, respectively, represent hydrogen, fluorine, chlorine, bromine, iodine, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, nitro, trifluoromethyl, cyano, CH n- or CH3 Cl-I2S (O) η ~, R 2 represents hydrogen, fluoro, chloro, bromo or methyl, R 4 represents hydrogen, fluoro, chloro, bromo, C 1-6 alkyl or C 1-6 alkoxy, R 5 represents hydrogen, fluoro, chloro, bromo, methyl or methoxy, 6 r8 means hydrogen, methyl, chlorine or bromine, 7 10 30. and R individually means hydrogen, methyl, chlorine or bromine, W and Q individually represent oxygen or sulfur, n is "0, 1 or 2 , 8 X represents hydrogen, chlorine, bromine, methyl, ethyl, C1-3 alkoxy, trifluoromethyl, CH3S or CH3OCH2-, and Z means methyl or methoxy, or agriculturally suitable salts thereof, however a) when R5 is other than hydrogen, at least one of the substituents R 1, R 2, R 6 and R 7 is different from hydrogen and at least two of the substituents R, R 2, R 2 and R f must be 5 hydrogen, 5 3 4 6 b) when R is hydrogen and all substituents R, R, R and 7 R are different from hydrogen, all substituents-3 4 6 7 ne R, R, R ° and R / must be either chlorine or methyl, and 3 7 c) when R and R both means hydrogen, at least one of the substituents R, R3 or R must be hydrogen. Chemical compound according to claim 1, characterized in that R 2 - represents r 3 R 4 R 5 R 7 R 6 3 R means hydrogen, fluoro, chloro, bromo, C 1-6 alkyl, C 2-4 alkoxy, CH 2 S- or CH 2 Cl 2 S-, R 5 represents hydrogen, fluoro, chloro, bromo or methyl, and 6 R means hydrogen, fluoro, chloro, bromo, alkyl, C 1-6 alkoxy, trifluoromethyl, nitro, CH 2 S-, or CH 2 Cl 2 S - except that (a) when R is different from hydrogen, R, R and R must each be hydrogen, fluorine, chlorine, bromine, methyl, or 4 methoxy and R must be hydrogen, fluorine, chlorine, bromine or methyl and when R is said pyrimidinyl group, X is methyl or C 1-4 alkoxy and Z is methyl or methoxy or when R is said triazinyl group, X is methyl or C1-3 alkoxy and Z is methoxy . Compound according to claim 1, characterized in that 35 / r 1 is A or As 1 / R 8 'R 9 R 10 149343 0 8. XO wherein R, R and R have the meanings set forth in claim 1 and when R is said pyrimidinyl group, Q is sulfur, X is methyl or C 1-6 alkoxy, and g Z is methyl or methoxy or when R is said triazine group, Q is sulfur, X is methyl or C 1-6 alkoxy, and Z is methoxy. A compound according to claim 1, characterized in that it is a) N - [(4-methoxy-6-methylpyrimidin-2-yl) aroinocarbonyl] -2-chlorobenzenesulfonamide., B) N - [(4,6- dimethoxypyrimidin-2-yl) aminocarbonyl] -2,5-dichlorobenzenesulfonamide, c) N - [(4-methoxy-6-methylpyrimidin-2-yl) aminocarbonyl] -2-methylbenzenesulfonamide, d) N- [( 4,6-dimethylpyrimidin-2-yl) aminocarbonyl] -2-thiophenesulfonamide, e) N - [(4-methoxy-6-methylpyrimidin-2-yl) aminocarbonyl] -2-chloro-5-methoxybenzenesulfonamide, f) N - [(4,6-dimethylpyrimidin-2-yl) aminocarbonyl] -2,6-dichlorobenzenesulfonamide, g) N - [(4,6-dimethylpyrimidin-2-yl) aminocarbonyl] -benzenesulfonamide , h) N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl} aminocarbonyl] -2-chlorobenzenesulfonamide, i) N - [(4,6-dimethoxy-1,3) (5-Triazin-2-yl) aminocarbonyl] -2-chlorobenzenesulfonamide, N) [(4,6-Dimethoxy-1,3,5-triazin-2-yl) aminocarbonyl] -2,5- dimethoxybenzenesulfonamide, k) N - [(4,6-dimethoxy-1,3,5-triazin-2-yl) aminocarbonyl] -benzenesulfonamide, 1) N - [(4-methoxy-6-methyl-1, 3,5-triazin-2-yl) aminocarbonyl] -2- 35-chloro-5-methoxybenzenesulfonamide, m) N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) aminocarbonyl ] - benzenesulfonamide or