US5081133A
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2-anilinocyanopyridines having fungicidal properties
Assignee: BASF SE
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Filing: 1990-01-25
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Granted: 1992-01-14
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Expires: 2010-01-25
Abstract
Abstract 2-Anilinocyanopyridines of the formula ##STR1## where X is NO 2 , CN, halogen, SO 2 -alkyl, alkyl, cycloalkyl, haloalkyl, alkoxy, or phenoxy or phenylthio which is unsubstituted or substituted in the phenyl, m is an integer from 1 to 3, R 1 is hydrogen, halogen, alkoxy, haloalkyl, haloalkoxy, or phenoxy or phenylthio which is unsubstituted or substituted in the phenyl, R 2 and R 3 are hydrogen, NO 2 , halogen, CN, alkyl, SO 2 -alkyl, haloalkyl, SO 2 NR 5 R 6 , haloalkoxy, COOR 5 or CONR 5 R 6 , R 4 is hydrogen, COOR 7 , CONR 5 R 6 , CHO, COR 7 , SO 2 R 7 , C 3 -C 6 -alkenyl or C 3 -C 6 -alkynyl, and salts of these 2-anilinocyanopyridines of the formula I in which R 4 is hydrogen with plant-tolerated cations, and fungicides containing these compounds.
Inventors
- 👤 Juergen Schubert
- 👤 Jochen Wild
- 👤 Albrecht Harreus
- 👤 Thomas Kuekenhoehner
- 👤 Hubert Sauter
- 👤 Eberhard Ammermann
- 👤 Gisela Lorenz
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 10:13
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/78; C07D213/84; A; A01; A01N; A01N43/00; A01N43/34; A01N43/40
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
308 words
A 2-anilinocyanopyridine of the formula I ##STR21## where X is H, NO 2 , CN, halogen, SO 2 --C 1 -C 4 -alkyl, C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, phenoxy, phenoxy substituted from one to three times with halogen or from one to two times with nitro or methyl, phenylthio or phenylthio substituted from one to three times with halogen or from one to two times with nitro or methyl, m is an integer from 1 to 3, with the individual radicals being identical or different when m is greater than 1, R 1 is hydrogen, halogen, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, phenoxy, phenoxy substituted from one to three times with halogen or from one to two times with nitro or methyl, phenylthio or phenylthio substituted from one to three times with halogen or from one to two times with nitro or methyl, R 2 and R 3 are, independently of one another, hydrogen, NO 2 , halogen, CN, C 1 -C 6 -alkyl, SO 2 --C 1 -C 4 -alkyl, C 1 -C 6 -haloalkyl, SO 2 NR 5 R 6 , C 1 -C 4 -haloalkoxy, COOR 5 or CONR 5 R 6 , R 4 is hydrogen, COOR 7 , CONR 5 R 6 , CHO, COR 7 , SO 2 R 7 , C 3 -C 6 -alkenyl or C3-C6-alkynyl, R 5 and R 6 are, independently of one another, hydrogen or C 1 -C 4 -alkyl, R 7 is C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, benzyl, phenyl, 2-tolyl, 3-tolyl, 4-tolyl, halophenyl, nitrophenyl, 1-naphthyl or 2-naphthyl, or a salt of said 2-anilinocyanopyridine of the formula I in which R 4 is hydrogen with a plant-tolerated cation.
Claim 2
Dependent Claim
308 words
A 2-anilinocyanopyridine of the formula I ##STR21## where X is H, NO 2 , CN, halogen, SO 2 --C 1 -C 4 -alkyl, C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, phenoxy, phenoxy substituted from one to three times with halogen or from one to two times with nitro or methyl, phenylthio or phenylthio substituted from one to three times with halogen or from one to two times with nitro or methyl, m is an integer from 1 to 3, with the individual radicals being identical or different when m is greater than 1, R 1 is hydrogen, halogen, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, phenoxy, phenoxy substituted from one to three times with halogen or from one to two times with nitro or methyl, phenylthio or phenylthio substituted from one to three times with halogen or from one to two times with nitro or methyl, R 2 and R 3 are, independently of one another, hydrogen, NO 2 , halogen, CN, C 1 -C 6 -alkyl, SO 2 --C 1 -C 4 -alkyl, C 1 -C 6 -haloalkyl, SO 2 NR 5 R 6 , C 1 -C 4 -haloalkoxy, COOR 5 or CONR 5 R 6 , R 4 is hydrogen, COOR 7 , CONR 5 R 6 , CHO, COR 7 , SO 2 R 7 , C 3 -C 6 -alkenyl or C3-C6-alkynyl, R 5 and R 6 are, independently of one another, hydrogen or C 1 -C 4 -alkyl, R 7 is C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, benzyl, phenyl, 2-tolyl, 3-tolyl, 4-tolyl, halophenyl, nitrophenyl, 1-naphthyl or 2-naphthyl, or a salt of said 2-anilinocyanopyridine of the formula I in which R 4 is hydrogen with a plant-tolerated cation.
Claim 3
Dependent Claim
37 words
A compound of the formula I as set forth in claim 1, where X m is 4-isopropyl, 3-cyano, 5-cyano, 6-ethoxy, R 1 is chlorine, R 2 is trifluoromethyl, R 3 is nitro and R 4 is hydrogen.
Claim 4
Dependent Claim
35 words
A compound of the formula I as set forth in claim 1, where X m is 3-chloro, 5-cyano, R 1 is hydrogen, R 2 is trifluoromethyl, R 3 is hydrogen and R 4 is benzenesulfonyl.
Claim 5
Dependent Claim
15 words
The A 2-anilinocyanopyridine of claim 1, wherein m is an integer from 1 to 2.
Claim 6
Dependent Claim
328 words
A fungicidal composition comprising a fungicidally effective amount of a compound of the formula I ##STR22## where X is H, NO 2 , CN, halogen, SO 2 --C 1 -C 4 -alkyl, C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, phenoxy, phenoxy substituted from one to three times with halogen or from one to two times with nitro or methyl, phenylthio or phenylthio substituted from one to three times with halogen or from one to two times with nitro or methyl, m is an integer from 1 to 3, with the individual radicals being identical or different when m is greater than 1, R 1 is hydrogen, halogen, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, phenoxy, phenoxy substituted from one to three times with halogen or from one to two times with nitro or methyl, phenylthio or phenylthio substituted from one to three times with halogen or from one to two times with nitro or methyl, R 2 and R 3 are, independently of one another, hydrogen, NO 2 , halogen, CN, C 1 -C 6 -alkyl, SO 2 --C 1 -C 4 -alkyl, C 1 -C 6 -haloalkyl, SO 2 NR 5 R 6 , C 1 -C 4 -haloalkoxy, COOR 5 or CONR 5 R 6 , R 4 is hydrogen, COOR 7 , CONR 5 R 6 , CHO, COR 7 , SO 2 R 7 , C 3 -C 6 -alkenyl or C 3 -C 6 -alkynyl, R 5 and R 6 are, independently of one another, hydrogen or C 1 -C 4 -alkyl, R 7 is C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, benzyl, phenyl, 2-tolyl, 3-tolyl, 4-tolyl, halophenyl, nitrophenyl, 1-naphthyl or 2-naphthyl, or a salt of said 2-anilinocyanopyridine of the formula I in which R 4 is hydrogen with a plant-tolerated cation in admixture with a suitable inert carrier.
Claim 7
Dependent Claim
328 words
A fungicidal composition comprising a fungicidally effective amount of a compound of the formula I ##STR22## where X is H, NO 2 , CN, halogen, SO 2 --C 1 -C 4 -alkyl, C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, phenoxy, phenoxy substituted from one to three times with halogen or from one to two times with nitro or methyl, phenylthio or phenylthio substituted from one to three times with halogen or from one to two times with nitro or methyl, m is an integer from 1 to 3, with the individual radicals being identical or different when m is greater than 1, R 1 is hydrogen, halogen, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, phenoxy, phenoxy substituted from one to three times with halogen or from one to two times with nitro or methyl, phenylthio or phenylthio substituted from one to three times with halogen or from one to two times with nitro or methyl, R 2 and R 3 are, independently of one another, hydrogen, NO 2 , halogen, CN, C 1 -C 6 -alkyl, SO 2 --C 1 -C 4 -alkyl, C 1 -C 6 -haloalkyl, SO 2 NR 5 R 6 , C 1 -C 4 -haloalkoxy, COOR 5 or CONR 5 R 6 , R 4 is hydrogen, COOR 7 , CONR 5 R 6 , CHO, COR 7 , SO 2 R 7 , C 3 -C 6 -alkenyl or C 3 -C 6 -alkynyl, R 5 and R 6 are, independently of one another, hydrogen or C 1 -C 4 -alkyl, R 7 is C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, benzyl, phenyl, 2-tolyl, 3-tolyl, 4-tolyl, halophenyl, nitrophenyl, 1-naphthyl or 2-naphthyl, or a salt of said 2-anilinocyanopyridine of the formula I in which R 4 is hydrogen with a plant-tolerated cation in admixture with a suitable inert carrier.
Claim 8
Dependent Claim
15 words
The fungicidal composition of claim 5, wherein m is an integer from 1 to 2.
Claim 9
Independent Claim
330 words
A method for combating fungi, comprising applying a fungicidally effective amount of a compound of the formula ##STR23## where X is H, NO 2 , CN, halogen, SO 2 --C 1 -C 4 -alkyl, C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, phenoxy, phenoxy substituted from one to three times with halogen or from one to two times with nitro or methyl, phenylthio or phenylthio substituted from one to three times with halogen or from one to two times with nitro or methyl, m is an integer from 1 to 3, with the individual radicals being identical or different when m is greater than 1, R 1 is hydrogen, halogen, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, phenoxy, phenoxy substituted from one to three times with halogen or from one to two times with nitro or methyl, phenylthio or phenylthio substituted from one to three times with halogen or from one to two times with nitro or methyl, R 2 and R 3 are, independently of one another, hydrogen, NO 2 , halogen, CN, C 1 -C 6 -alkyl, SO 2 --C 1 -C 4 -alkyl, C 1 -C 6 -haloalkyl, SO 2 NR 5 R 6 , C 1 -C 4 -haloalkoxy, COOR 5 or CONR 5 R 6 , R 4 is hydrogen, COOR 7 , CONR 5 R 6 , CHO, COR 7 , SO 2 R 7 , C 3 -C 6 -alkenyl or C 3 -C 6 -alkynyl, R 5 and R 6 are, independently of one another, hydrogen or C 1 -C 4 -alkyl, R 7 is C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, benzyl, phenyl, 2-tolyl, 3-tolyl, 4-tolyl, halophenyl, nitrophenyl, 1-naphthyl or 2-naphthyl, or a salt of said 2-anilinocyanopyridine of the formula I in which R 4 is hydrogen with a plant-tolerated cation to a locus subject to fungal infection.
Claim 10
Independent Claim
330 words
A method for combating fungi, comprising applying a fungicidally effective amount of a compound of the formula ##STR23## where X is H, NO 2 , CN, halogen, SO 2 --C 1 -C 4 -alkyl, C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, phenoxy, phenoxy substituted from one to three times with halogen or from one to two times with nitro or methyl, phenylthio or phenylthio substituted from one to three times with halogen or from one to two times with nitro or methyl, m is an integer from 1 to 3, with the individual radicals being identical or different when m is greater than 1, R 1 is hydrogen, halogen, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, phenoxy, phenoxy substituted from one to three times with halogen or from one to two times with nitro or methyl, phenylthio or phenylthio substituted from one to three times with halogen or from one to two times with nitro or methyl, R 2 and R 3 are, independently of one another, hydrogen, NO 2 , halogen, CN, C 1 -C 6 -alkyl, SO 2 --C 1 -C 4 -alkyl, C 1 -C 6 -haloalkyl, SO 2 NR 5 R 6 , C 1 -C 4 -haloalkoxy, COOR 5 or CONR 5 R 6 , R 4 is hydrogen, COOR 7 , CONR 5 R 6 , CHO, COR 7 , SO 2 R 7 , C 3 -C 6 -alkenyl or C 3 -C 6 -alkynyl, R 5 and R 6 are, independently of one another, hydrogen or C 1 -C 4 -alkyl, R 7 is C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, benzyl, phenyl, 2-tolyl, 3-tolyl, 4-tolyl, halophenyl, nitrophenyl, 1-naphthyl or 2-naphthyl, or a salt of said 2-anilinocyanopyridine of the formula I in which R 4 is hydrogen with a plant-tolerated cation to a locus subject to fungal infection.
Claim 11
Dependent Claim
17 words
The method for combating fungi of claim 7, wherein m is an integer from 1 to 2.
References Cited (Backward Citations)
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