Sulfonamide derivatives

a technology of sulfonamide and derivatives, which is applied in the direction of amide active ingredients, heterocyclic compound active ingredients, biocide, etc., can solve the problems of resistance to microorganisms and no sulfonamide derivatives have been developed, and achieve excellent microorganismicidal effects

Inactive Publication Date: 2004-02-05
TABUCHI TAKANORI +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

0003] The present inventors have made intensive efforts for many years in order to find out compounds which have excellent microbicidal action and solve the problems mentioned above. As the results, they have found that the compounds represented by the formula I.sup.0 or salts thereof. 2

Problems solved by technology

However, it is well-known that frequent use of restricted number of compounds has led to outbreak of microbes which are resistant to those drugs.
Nevertheless, no sulfonamide derivative has been developed yet, which is safe and has little influence on human beings and firm animals, natural enemies, and the environment, and exert excellent protective effects even on drug-resistant microbes.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

example 1

[0576] Synthesis of 2',4'-Dichloro-N-methyl-p-toluenesulfonanilide

[0577] (Compound No. 51)

[0578] To a suspension of sodium hydride(60%, 0.07g (1.75 mmol)) in DMF (2.0 ml), 2',4'-dichloro-p-toluenesulfonanilide(0.50 g (1.58 mmol)) was added with stirring at room temperature. To the resulting mixture, after 15 minutes' stirring at room temperature, dimethyl sulfate(0.17 ml (1.80 mmol)) was added dropwise. After 15 hours' stirring at room temperature, the reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with water and saturated sodium chloride solution, successively, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The crystals separated were filtered and washed with diisopropyl ether to give 0.38 g (73%) of the title compound.

[0579] mp: 86.0-87.0.degree. C.

[0580] NMR(CDl.sub.3) .delta.: 2.44(3H,s), 3.17(3H,s), 7.13(1H,d,J=8.6 Hz), 7.22(1H,dd,J=8.6& 2.3 Hz), 7.30(2H,d,J=8.4 Hz), 7.42(1H,d,J=2.3 Hz), 7.6...

example 2

[0581] Synthesis of N,4'-Dimethyl-3'-nitro-p-toluenesulfonanilide

[0582] (Compound No. 126)

[0583] To a suspension of sodium hydride (60%, 0.14g (3.50 mmol)) in DMF (3.0 ml), 4'-methyl-3'-nitro-p-toluenesulfonanilide (1.00 g (3.26 mmol)) was added with stirring at room temperature. To the resulting mixture, after 15 minutes' stirring at room temperature, dimethyl sulfate (0.34 ml (3.56 mmol)) was added dropwise. After one hours' stirring at room temperature, the reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with water and saturated sodium chloride solution, successively, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. Diethyl ether was added to the residue, and the solid separated was filtered and washed to give 0.79 g (76%) of the title compound as pale yellow crystals.

[0584] mp: 103.5-106.0.degree. C.

[0585] NMR(CDCl.sub.3) .delta.: 2.43(3H,s), 2.59(3H,s), 3.17(3H,s), 7.27(2H,d,J=8.3 Hz), 7.31(1H,...

example 3

[0586] Synthesis of N-Ethyl-4'-fluoro-2'-nitro-p-toluenesulfonanilide

[0587] (Compound No. 263)

[0588] To a suspension of sodium hydride (60%, 0.05 g (1.25 mmol)) in DMF (2.0 ml), 4'-fluoro-2'-nitro-p-toluenesulfonanilide (0.31 g (1.00 mmol)) was added with stirring at room temperature. To the resulting mixture, after 15 minutes' stirring at room temperature, ethyl iodide (0.30 ml (3.75 mmol)) was added dropwise. After 30 minutes' heating at 100.degree. C. with stirring, the reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with water and saturated sodium chloride solution, successively, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. Diisopropyl ether was added to the residue and the solid separated was filtered and washed to give 0.25 g (74%) of the title compound as pale yellow crystals.

[0589] mp: 93.0-94.5.degree. C.

[0590] NMR(CDCl.sub.3) .delta.: 1.18(3H,s), 2.44(3H,s), 3.67(2H,brq,J=7.2 Hz), 7.10...

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Abstract

The present invention relates to microbicides for agricultural or horticultural use containing sulfonamide derivative of, for example, a formula (I): or a salt thereof, [wherein A<1 >is (1) an aryl group which may be substituted or (2) a heterocyclic group which may be substituted, X<1 >is (1) a chemical bond, (2) a methylene group which may be substituted, or (3) a vinylene group which may be substituted, B<1 >is a five-membered heterocyclic group comprising nitrogen or sulfur atoms as the ring-constructing atoms except for carbon atoms and may be substituted or a condensed heterocyclic group which may be substituted, Z<1 >is (1) a hydrocarbon group which may be substituted, (2) an acyl group which may be substituted, (3) formyl group, (4) an amino group which may be substituted, (5) a group represented by -N=CR<1>R<2 >(wherein each of R<1 >and R<2 >is a hydrogen atom or a hydrocarbon group which may be substituted), (6) a cyclic amino group, (7) a group represented by -OR<3 >(wherein R<3 >is a hydrogen atom, a hydrocarbon group which may be substituted, an acyl group which may be substituted, formyl group or an alkylsulfonyl group which may be substituted) or (8) -S(O)nR<4 >(wherein n stands for an integer from 0 to 2, R<4 >stands for a hydrogen atom or a hydrocarbon group which may be substituted). The said compounds or the salts thereof are sulfonamide derivatives with microbicidal action, are useful as excellent microbicides for agricultural or horticultural use, because they are safe, and they have little influence on human beings, farm animals, natural enemies, or the environment, and exert excellent control effects even on resistant microbes.

Description

[0001] This invention relates to sulfonamide derivatives useful as microbicides for agricultural or horticultural use.[0002] A lot of microbicides have ever been synthesized and used as microbicides for agriculture or horticulture. They have contributed greatly to supply agricultural products constantly. However, it is well-known that frequent use of restricted number of compounds has led to outbreak of microbes which are resistant to those drugs. In addition, recent rise in demand for the safety and environmental influence of chemical substances has made it desirable to develop safer microbicides for agricultural or horticultural use. This has given an intention to the researches to explore and research novel compounds with microbicidal activity. As for sulfonamide derivatives, a lot of compounds have also been synthesized so far from the interests in their biological or chemical characteristics. A majority of them are, however, synthetic intermediates, medicines, compounds prepare...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): A01N41/06A01N43/10A01N43/40A01N43/42A01N43/50A01N43/56A01N43/58A01N43/60A01N43/653A01N43/80A01N43/82A01N43/90C07C311/13C07C311/21C07C311/29C07C311/44C07C311/46C07C311/48C07C311/49C07C311/51C07C317/36C07C317/48C07C323/49C07C323/63C07C327/48C07C327/58
CPCA01N41/06A01N43/10C07C2101/02A01N43/40A01N43/42A01N43/50A01N43/56A01N43/58A01N43/60A01N43/653A01N43/80A01N43/82A01N43/90C07C311/13C07C311/21C07C311/29C07C311/44C07C311/46C07C311/48C07C311/49C07C311/51C07C317/36C07C317/48C07C323/49C07C323/63C07C327/48C07C327/58A01N2300/00C07C2601/02
Inventor TABUCHI, TAKANORIYAMAMOTO, TETSUHIRONAKAYAMA, MASAHARU
Owner TABUCHI TAKANORI
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