US4551478A
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US
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3-Nitrobenzene sulfonanilide derivatives and fungicidal compositions for the control of plant diseases containing same
Assignee: Mitsui Toatsu Chemicals Inc
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Filing: 1982-12-30
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Granted: 1985-11-05
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Expires: 2002-12-30
Abstract
Abstract Disclosed are novel 3-nitrobenzene sulfonanilide derivatives and, among others, that of the formula <IMAGE> as well as fungicidal compositions containing such compounds as the active ingredient. The compounds of the invention are markedly effective in controlling plant diseases and, in particular, clubroot disease of Brassica spp., have no toxicity to men, beasts, and fishes, exert no phytotoxicity on crops, have neither irritant nor unpleasant odor, and manifest their excellent fungicidal effect at low concentrations. Accordingly, they are ideally useful in fungicidal compositions.
Inventors
- 👤 Tekeo Yoshimoto
- 👤 Mitsumasa Umemoto
- 👤 Keiichi Igarashi
- 👤 Hideo Yamazaki
- 👤 Yoshio Takasawa
- 👤 Hirohisa Yanagita
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 12:44
CPC Classifications
A; A01; A01N; A01N41/00; A01N41/02; A01N41/04; A01N41/06
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
95 words
A 3-nitrobenzene sulfonanilide derivative having the formula: ##STR6## wherein R 1 and R 2 are both hydrogen, R 1 is hydrogen and R 2 is methyl or R 1 is methyl and R 2 is hydrogen, and when R 1 and R 2 are both hydrogen, (X) n is 2,4,6-trichloro, 2-chloro-4-nitro or 2-chloro-5-nitro; when R 1 is hydrogen and R 2 is methyl, (X) n is 4-iodo, 2,5-dichloro, 3,5-dichloro, 2-bromo-4,5-dichloro or 2-chloro-4-nitro; and when R 1 is methyl and R 2 is hydrogen, (X) n is 4-iodo, 2,3-dichloro, 2,5-dichloro, 3,5-dichloro, 2-bromo-4,5-dichloro, 2-chloro-5-nitro, 2-methyl-6-nitro or 2-nitro-4-methyl.
Claim 2
Dependent Claim
95 words
A 3-nitrobenzene sulfonanilide derivative having the formula: ##STR6## wherein R 1 and R 2 are both hydrogen, R 1 is hydrogen and R 2 is methyl or R 1 is methyl and R 2 is hydrogen, and when R 1 and R 2 are both hydrogen, (X) n is 2,4,6-trichloro, 2-chloro-4-nitro or 2-chloro-5-nitro; when R 1 is hydrogen and R 2 is methyl, (X) n is 4-iodo, 2,5-dichloro, 3,5-dichloro, 2-bromo-4,5-dichloro or 2-chloro-4-nitro; and when R 1 is methyl and R 2 is hydrogen, (X) n is 4-iodo, 2,3-dichloro, 2,5-dichloro, 3,5-dichloro, 2-bromo-4,5-dichloro, 2-chloro-5-nitro, 2-methyl-6-nitro or 2-nitro-4-methyl.
Claim 3
Dependent Claim
17 words
The 3-nitrobenzene sulfonanilide derivative of claim 1 wherein, in the general formula (I), (X) n is 2-chloro-4-nitro.
Claim 4
Dependent Claim
151 words
A fungicidal composition for controlling soil-borne plant diseases containing, as the active ingredient, in the range of 2 to 5 weight percent for dusts, granules, and fine granules; in the range of 40 to 60 weight percent for wettable powders and flowable formulations; and in the range of 30 to 50 weight percent for emulsifiable concentrates, a 3-nitrobenzene sulfonanilide derivative having the formula: ##STR7## wherein R 1 and R 2 are both hydrogen, R 1 is hydrogen and R 2 is methyl or R 1 is methyl and R 2 is hydrogen, and when R 1 and R 2 are both hydrogen, (X) n is 2,4,6-trichloro, 2-chloro-4-nitro or 2-chloro-5-nitro; when R 1 is hydrogen and R 2 is methyl, (X) n is 4-iodo, 2,5-dichloro, 3,5-dichloro, 2-bromo-4,5-dichloro or 2-chloro-4-nitro; and when R 1 is methyl and R 2 is hydrogen, (X) n is 4-iodo, 2,3-dichloro, 2,5-dichloro, 3,5-dichloro, 2-bromo-4,5-dichloro, 2-chloro-5-nitro, 2-methyl-6-nitro or 2-nitro-4-methyl.
Claim 5
Dependent Claim
151 words
A fungicidal composition for controlling soil-borne plant diseases containing, as the active ingredient, in the range of 2 to 5 weight percent for dusts, granules, and fine granules; in the range of 40 to 60 weight percent for wettable powders and flowable formulations; and in the range of 30 to 50 weight percent for emulsifiable concentrates, a 3-nitrobenzene sulfonanilide derivative having the formula: ##STR7## wherein R 1 and R 2 are both hydrogen, R 1 is hydrogen and R 2 is methyl or R 1 is methyl and R 2 is hydrogen, and when R 1 and R 2 are both hydrogen, (X) n is 2,4,6-trichloro, 2-chloro-4-nitro or 2-chloro-5-nitro; when R 1 is hydrogen and R 2 is methyl, (X) n is 4-iodo, 2,5-dichloro, 3,5-dichloro, 2-bromo-4,5-dichloro or 2-chloro-4-nitro; and when R 1 is methyl and R 2 is hydrogen, (X) n is 4-iodo, 2,3-dichloro, 2,5-dichloro, 3,5-dichloro, 2-bromo-4,5-dichloro, 2-chloro-5-nitro, 2-methyl-6-nitro or 2-nitro-4-methyl.
Claim 6
Dependent Claim
29 words
The fungicidal composition of claim 3 wherein, in the general formula (I), (X) n is 2-chloro-4-nitro, R 1 is a hydrogen atom and R 2 is a methyl radical.
Claim 7
Dependent Claim
16 words
The fungicidal composition of claim 3 which is effective in controlling clubroot disease of Brassica spp.
Claim 8
Dependent Claim
16 words
The fungicidal composition of claim 4 which is effective in controlling clubroot disease of Brassica spp.
Claim 9
Independent Claim
158 words
A method of controlling clubroot disease of Brassica spp. which comprises, prior to the planting of a crop of the genus Brassica, applying a 3-nitrobenzene sulfonanilide derivative to the field in an amount of 5 to 20 kilograms per hectare, the 3-nitrobenzene sulfonanilide derivative having the general formula: ##STR8## wherein R 1 and R 2 each represent a hydrogen atom or a methyl radical, X represents a halogen atom, a methyl radical, or a nitro group, n is a whole number of 1 to 3, and when n is equal to 2 or 3, the atoms or radicals represented by X may be identical to or different from each other but the four compounds in which R 1 and R 2 are both hydrogen atoms and (X) n is 4-chloro, 3,4-dichloro, 2,4-dichloro or 2,5-dichloro and the compound in which R 1 is a methyl radical, R 2 is a hydrogen atom and (X) n is 2-chloro-4-nitro are excluded.
Claim 10
Independent Claim
158 words
A method of controlling clubroot disease of Brassica spp. which comprises, prior to the planting of a crop of the genus Brassica, applying a 3-nitrobenzene sulfonanilide derivative to the field in an amount of 5 to 20 kilograms per hectare, the 3-nitrobenzene sulfonanilide derivative having the general formula: ##STR8## wherein R 1 and R 2 each represent a hydrogen atom or a methyl radical, X represents a halogen atom, a methyl radical, or a nitro group, n is a whole number of 1 to 3, and when n is equal to 2 or 3, the atoms or radicals represented by X may be identical to or different from each other but the four compounds in which R 1 and R 2 are both hydrogen atoms and (X) n is 4-chloro, 3,4-dichloro, 2,4-dichloro or 2,5-dichloro and the compound in which R 1 is a methyl radical, R 2 is a hydrogen atom and (X) n is 2-chloro-4-nitro are excluded.
Claim 11
Dependent Claim
28 words
The method of claim 7 wherein, in the general formula (I), (X) n is 2-chloro-4-nitro, R 1 is a hydrogen atom and R 2 is a methyl radical.
References Cited (Backward Citations)
US3034955A
Cited
DE1163838B
Cited
US3804586A
Cited
US4021229A
Cited
US4113463A
Cited
JPS5731655A
Cited
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| 3.5 Years (Year 4) | 1988-11-04 | 1989-05-06 | 1989-11-05 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-11-04 | 1993-05-06 | 1993-11-05 | $3760.00 | Window Closed / Lapsed |
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