Use of sulfonanilides as agricultural and horticultural fungicide
View Patent ↗Compounds of the formula (I), wherein Z represents C—R 7 or N, and R 5 represents alkyl that may be optionally substituted, alkenyl, alkynyl, cycloalkyl or alkoxycarbonylamino, are useful as agricultural and horticultural fungicides.
1. Sulfonanilides represented by the formula
wherein
X A represents hydrogen, alkyl, halogen, alkoxycarbonyl, acyl, dialkylaminocarbonyl, alkoxy, alkylsulfonyl, alkylsulfonyloxy, dialkylamino, haloalkoxy, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, haloalkylsulfonyloxy, formyl, carboxy, cyano, nitro or phenoxy,
Y A represents halogen, alkoxyalkyl, alkoxycarbonyl, acyl, alkoxy, alkylsulfonyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, dialkylamino, cyano, nitro, or alkyl that may be optionally substituted by one or more halogens and 2 or 3 Y A 's may be identical or different each other in case that n is 2 or 3,
Z A represents N,
n represents an integer of 0 to 3,
R 1A and R 2A each independently represents hydrogen, halogen, cycloalkyl, alkoxy, haloalkoxy, alkylthio, or alkyl that may be optionally substituted by one or more halogens,
R 3A and R 4A each independently represents hydrogen, halogen, alkyl, alkoxy, alkylthio or alkylsulfonyl, or
R 3A represents hydroxy and R 4A represents hydrogen or alkyl, or
R 3A and R 4A together may form C═O with the carbon atom to which they are bonded,
R 6A represents hydrogen, alkoxyalkyl, alkoxycarbonyl, acyl, group —SO 2 R 5A , or alkyl that may be optionally substituted by one or more halogens,
R 5A represents alkyl that may be optionally substituted by one or more halogens, and
R 7A represents hydrogen or alkyl,
with the exception of the following cases (T-1) or (T-3);
(T-1) the case in which X A represents alkyl, and n represents 0,
(T-3) the case in which X A represents halogen, n represents 0, Z A represents N, R 1A and R 2A represent methoxy, R 3A and R 4A represent hydrogen, R 3A represents hydroxyl and R 4A represents hydrogen, or R 3A and R 4A together form C═O with the carbon atom to which they are bonded, and R 6A represents hydrogen.
2. Compounds set forth in claim 1 , wherein
X A represents hydrogen, fluorine, chlorine, C 1-6 alkyl, C 1-6 alkoxy-carbonyl, C 1-6 alkyl-carbonyl, C 3-7 cycloalkyl-carbonyl, di(C 1-6 alkyl)aminocarbonyl, C 1-6 alkoxy, C 1-6 alkylsulfonyl, C 1-6 alkylsulfonyloxy, di(C 1-6 alkyl)amino, C 1-6 haloalkoxy, C 1-6 haloalkylthio, C 1-6 haloalkylsulfinyl, C 1-6 haloalkylsulfonyl, C 1-6 haloalkylsulfonyloxy, formyl, carboxy, cyano, nitro or phenoxy,
Y A represents fluorine, chlorine, C 1-6 alkyl, where at least one hydrogen of which may be optionally halogen-substituted, C 1-6 alkoxy-C 1-6 alkyl, C 1-6 alkoxy-carbonyl, C 1-6 alkyl-carbonyl, C 1-6 alkoxy, C 1-6 alkylsulfonyl, C 1-6 haloalkoxy, C 1-6 haloalkylthio, C 1-6 haloalkylsulfinyl, C 1-6 haloalkylsulfonyl, di(C 1-6 alkyl)amino, cyano or nitro, and 2 Y A 's may be identical or different each other in case that n is 2,
Z A represents N,
n represents 0, 1 or 2,
R 1A and R 2A each independently represents hydrogen, chlorine, C 1-6 alkyl, where at least one hydrogen of which may be optionally halogen-substituted, C 3-7 cycloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy or C 1-6 alkylthio,
R 3A and R 4A each independently represents hydrogen, fluorine, chlorine, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkylthio or C 1-6 alkylsulfonyl,
R 3A represents hydroxy and R 4A represents hydrogen or C 1-6 alkyl, or
R 3A and R 4A together may form C═O with the carbon atom to which they are bonded,
R 6A represents hydrogen, C 1-6 alkyl, where at least one hydrogen of which may be optionally halogen-substituted, C 1-6 alkoxy-C 1-6 alkyl, C 1-6 alkoxy-carbonyl, C 1-6 alkyl-carbonyl, C 3-7 cycloalkyl-carbonyl, or group —SO 2 R 5A ,
R 5A represents C 1-6 alkyl, C 1-6 haloalkyl or cyano-substituted C 1-6 alkyl, and
R 7A represents hydrogen or C 1-6 alkyl,
with the exception of the following cases (T-1) or (T-3);
(T-1) the case in which X A represents alkyl, and n represents 0,
(T-3) the case in which X A represents halogen, n represents 0, Z A represents N, R 1A and R 2A represent methoxy, R 3A and R 4A represent hydrogen, R 3A represents hydroxyl and R 4A represents hydrogen, or R 3A and R 4A together form C═O with the carbon atom to which they are bonded, and R 6A represents hydrogen.
3. Compounds set forth in claim 1 , wherein
X A represents hydrogen, fluorine, chlorine, C 1-4 alkyl, C 1-4 alkoxy-carbonyl, C 1-4 alkyl-carbonyl, C 3-5 cycloalkyl-carbonyl, di(C 1-4 alkyl)aminocarbonyl, C 1-4 alkoxy, C 1-4 alkylsulfonyl, C 1-4 alkylsulfonyloxy, di(C 1-4 alkyl)amino, C 1-4 haloalkoxy, C 1-4 haloalkylthio, C 1-4 haloalkylsulfinyl, C 1-4 haloalkylsulfonyl, C 1-4 haloalkylsulfonyloxy, formyl, carboxy, cyano, nitro or phenoxy,
Y A represents fluorine, chlorine, C 1-4 alkyl, where at least one hydrogen of which may be optionally halogen-substituted, C 1-4 alkoxy-C 1-4 alkyl, C 1-4 alkoxy-carbonyl, C 1-4 alkyl-carbonyl, C 1-4 alkoxy, C 1-4 alkylsulfonyl, C 1-4 haloalkoxy, C 1-4 haloalkylthio, C 1-4 haloalkylsulfinyl, C 1-4 haloalkylsulfonyl, di(C 1-4 alkyl)amino, cyano or nitro, and 2 Y A 's may be identical or different each other in case that n is 2,
Z A represents N,
n represents 0, 1 or 2,
R 1A and R 2A each independently represents hydrogen, chlorine, C 1-4 alkyl, where at least one hydrogen of which may be optionally halogen-substituted, C 3-5 cycloalkyl, C 1-4 alkoxy, C 1-4 haloalkoxy or C 1-4 alkylthio,
R 3A and R 4A each independently represents hydrogen, fluorine, chlorine, C 1-4 alkyl, C 1-4 alkoxy, C 1-4 alkylthio or C 1-4 alkylsulfonyl,
R 3A represents hydroxy and R 4A represents hydrogen or C 1-4 alkyl, or
R 3A and R 4A together may form C═O with the carbon atom to which they are bonded,
R 6A represents hydrogen, C 1-4 alkyl, where at least one hydrogen of which may be optionally halogen-substituted, C 1-4 alkoxy-C 1-4 alkyl, C 1-4 alkoxy-carbonyl, C 1-4 alkyl-carbonyl, C 3-5 cycloalkyl-carbonyl, or group —SO 2 R 5A ,
R 5A represents C 1-4 alkyl, C 1-4 haloalkyl or cyano-substituted C 1-4 alkyl, and
R 7A represents hydrogen or C 1-4 alkyl,
with the exception of the following cases (T-1) or (T-3);
(T-1) the case in which X A represents alkyl, and n represents 0,
(T-3) the case in which X A represents halogen, n represents 0, Z A represents N, R 1A and R 2A represent methoxy, R 3A and R 4A represent hydrogen, R 3A represents hydroxyl and R 4A represents hydrogen, or R 3A and R 4A together form C═O with the carbon atom to which they are bonded, and R 6A represents hydrogen.
4. The sulfonanilides of claim 1 , wherein:
X A represents halogen,
Z A represents N,
n represents 0,
R 1A and R 2A each independently represent C 1 -C 6 -alkoxy,
R 3A represents hydroxyl, R 4A represents hydrogen, or
R 3A and R 4A together may form C═O, and
R 6A represents C 1 -C 4 alkyl.
5. The sulfonanilides of claim 4 , wherein:
X A represents fluorine,
R 1A and R 2A each represent methoxy, and
R 6A represents methyl.
6. The sulfonanilides of claim 1 , wherein:
X A represents alkyl, halogen, alkoxycarbonyl, acyl, dialkylaminocarbonyl, alkoxy, alkylsulfonyl, alkylsulfonyloxy, dialkylamino, haloalkoxy, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, haloalkylsulfonyloxy, formyl, carboxy, cyano, nitro or phenoxy,
Z A represents N,
n represents 0,
R 1A and R 2A each independently represents hydrogen, halogen, cycloalkyl, alkoxy, haloalkoxy, alkylthio, or alkyl that may be optionally substituted by one or more halogens,
R 3A and R 4A each independently represents hydrogen, halogen, alkyl, alkoxy, alkylthio or alkylsulfonyl, or
R 3A represents hydroxy and R 4A represents hydrogen or alkyl, or
R 3A and R 4A together may form C═O with the carbon atom to which they are bonded,
R 6A represents hydrogen or alkyl that may be optionally substituted by one or more halogens,
with the exception of the following cases (T-1) or (T-3);
(T-1) the case in which X A represents alkyl, and n represents 0,
(T-3) the case in which X A represents halogen, n represents 0, Z A represents N, R 1A and R 2A represent methoxy, R 3A and R 4A represent hydrogen, R 3A represents hydroxy and R 4A represents hydrogen, or R 3A and R 4A together form C═O with the carbon atom to which they are bonded, and R 6A represents hydrogen.
7. The sulfonanilides of claim 6 , wherein:
X A represents fluorine, chlorine, C 1-6 -alkyl, C 1-6 alkoxy-carbonyl, C 1-6 alkyl-carbonyl, C 3-7 cycloalkyl-carbonyl, di(C 1-6 alkyl)aminocarbonyl, C 1-6 alkoxy, C 1-6 alkylsulfonyl, C 1-6 alkylsulfonyloxy, di(C 1-6 alkyl)amino, C 1-6 haloalkoxy, C 1-6 haloalkylthio, C 1-6 haloalkylsulfinyl, C 1-6 haloalkylsulfonyl, C 1-6 haloalkylsulfonyloxy, formyl, carboxy, cyano, nitro or phenoxy,
R 1A and R 2A each independently represents hydrogen, chlorine, C 1-6 alkyl, where at least one hydrogen of which may be optionally halogen-substituted, C 3-7 cycloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy or C 1-6 alkylthio,
R 3A and R 4A each independently represents hydrogen, fluorine, chlorine, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkylthio or C 1-6 alkylsulfonyl,
R 3A represents hydroxy and R 4A represents hydrogen or C 1-6 alkyl, or
R 3A and R 4A together may form C═O with the carbon atom to which they are bonded,
R 6A represents hydrogen or C 1-6 alkyl, where at least one hydrogen of which may be optionally halogen-substituted, R 5A represents C 1-6 alkyl, C 1-6 haloalkyl or cyano-substituted C 1-6 alkyl, and
with the exception of the following cases (T-1) or (T-3);
(T-1) the case in which X A represents C 1-6 alkyl, and n represents 0,
(T-3) the case in which X A represents fluorine or chlorine, n represents 0, Z A represents N, R 1A and R 2A represent methoxy, R 3A and R 4A represent hydrogen, R 3A represents hydroxy and R 4A represents hydrogen, or R 3A and R 4A together form C═O with the carbon atom to which they are bonded, and R 6A represents hydrogen.
8. The sulfonanilides of claim 7 , wherein
X A represents hydrogen, fluorine, chlorine, C 1-4 alkyl, C 1-4 alkoxy-carbonyl, C 1-4 alkyl-carbonyl, C 3-5 cycloalkyl-carbonyl, di(C 1-4 alkyl)aminocarbonyl, C 1-4 alkoxy, C 1-4 alkylsulfonyl, C 1-4 alkylsulfonyloxy, di(C 1-4 alkyl)amino, C 1-4 haloalkoxy, C 1-4 haloalkylthio, C 1-4 haloalkylsulfinyl, C 1-4 haloalkylsulfonyl, C 1-4 haloalkyl-sulfonyloxy, formyl, carboxy, cyano, nitro or phenoxy,
R 1A and R 2A each independently represents hydrogen, chlorine, C 1-4 alkyl, where at least one hydrogen of which may be optionally fluoro-substituted, C 3-5 cycloalkyl, C 1-4 alkoxy, C 1-4 haloalkoxy or C 1-4 alkylthio,
R 3A and R 4A each independently represents hydrogen, fluorine, chlorine, C 1-4 alkyl, C 1-4 alkoxy, C 1-4 alkylthio or C 1-4 alkylsulfonyl,
R 3A represents hydroxy and R 4A represents hydrogen or C 1-4 alkyl, or
R 3A and R 4A together may form C═O with the carbon atom to which they are bonded,
R 6A represents hydrogen or C 1-4 alkyl, where at least one hydrogen of which may be optionally fluoro-substituted,
with the exception of the following cases (T-1) or (T-3);
(T-1) the case in which X A represents C 1-4 alkyl, and n represents 0,
(T-3) the case in which X A represents fluorine or chlorine, n represents 0, Z A represents N, R 1A and R 2A represent methoxy, R 3A and R 4A represent hydrogen, R 3A represents hydroxy and R 4A represents hydrogen, or R 3A and R 4A together form C═O with the carbon atom to which they are bonded, and R 6A represents hydrogen.