US4608385A
Expired / Lapsed
US
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Fungicidal N-phenylcarbamates
Assignee: Sumitomo Chemical Co Ltd
•
Filing: 1982-10-22
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Granted: 1986-08-26
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Expires: 2002-10-22
Abstract
Abstract Use of an N-phenylcarbamate of the formula: <IMAGE> as a fungicidal agent against phytopathogenic fungi, particularly their strains resistant to benzimidazole thiophanate fungicides and/or cyclic imide fungicides.
Inventors
- 👤 Hiroshi Noguchi
- 👤 Toshiro Kato
- 👤 Junya Takahashi
- 👤 Yukio Ishiguri
- 👤 Shigeo Yamamoto
- 👤 Katsuzo Kamoshita
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 21:16
CPC Classifications
C; C07; C07D; C07D307/00; C07D307/02; C07D307/34; C07D307/38; C07D307/40; C07D307/42; A; A01; A01N; A01N47/00; A01N47/08; A01N47/10; A01N47/20; A01N47/24; C07D307/04; C07D307/18; C07D307/20
Claims Analysis
Total Claims: 46
Claim 1
Independent Claim
367 words
A fungicidal composition which comprises as an active ingredient a fungicidally effective amount of an N-phenylcarbamate of the formula: ##STR79## wherein R 1 and R 2 are, same or different, a lower alkyl group, a lower alkenyl group, a lower alkynyl group or a lower alkyl group substituted with at least one member selected from the group consisting of halogen, lower alkoxy and lower cycloalkyl; R 3 is a C 1 -C 8 alkyl group, a C 3 -C 8 alkenyl group, a C 3 -C 8 alkynyl group, lower cycloalkyl group, a lower haloalkenyl group, a lower haloalkynyl group, a lower aralkyl group, a lower alkyl group substituted with at least one member selected from the group consisting of halogen, cyano, lower alkoxy, lower alkenyloxy, lower haloalkoxy, phenoxy, lower aralkyloxy and lower cycloalkyl, or a group of the formula: ##STR80## in which m is 0, 1 or 2, n is 1, 2 or 3; X and Y are, same or different, an oxygen atom or a sulfur atom; and Z is a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower cycloalkyl group, a lower haloalkenyl group, a lower alkyl group substituted with at least one member selected from the group consisting of halogen, cyano, lower alkoxy and lower alkoxycarbonyl, or a group of the formula: --COR 4 or --SO 2 R 4 in which R 4 is a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower cycloalkyl group, a lower haloalkenyl group, a lower alkyl group substituted with at least one member selected from the group consisting of halogen, cyano, lower alkoxy, lower cycloalkyl and phenoxy (phenoxy being optionally substituted with at least one halogen and/or at least one alkyl), a phenyl group, a furyl group, a thienyl group, a phenyl group substituted with at least one member selected from the group consisting of halogen, cyano, nitro, trifluoromethyl, lower alkyl and lower alkoxy, or an aralkyl group (aralkyl being optionally substituted with at least one halogen and/or at least one alkyl), with the proviso that when R 1 is methyl, R 2 is neither methyl nor butyl, and an inert carrier or diluent.
Claim 2
Dependent Claim
367 words
A fungicidal composition which comprises as an active ingredient a fungicidally effective amount of an N-phenylcarbamate of the formula: ##STR79## wherein R 1 and R 2 are, same or different, a lower alkyl group, a lower alkenyl group, a lower alkynyl group or a lower alkyl group substituted with at least one member selected from the group consisting of halogen, lower alkoxy and lower cycloalkyl; R 3 is a C 1 -C 8 alkyl group, a C 3 -C 8 alkenyl group, a C 3 -C 8 alkynyl group, lower cycloalkyl group, a lower haloalkenyl group, a lower haloalkynyl group, a lower aralkyl group, a lower alkyl group substituted with at least one member selected from the group consisting of halogen, cyano, lower alkoxy, lower alkenyloxy, lower haloalkoxy, phenoxy, lower aralkyloxy and lower cycloalkyl, or a group of the formula: ##STR80## in which m is 0, 1 or 2, n is 1, 2 or 3; X and Y are, same or different, an oxygen atom or a sulfur atom; and Z is a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower cycloalkyl group, a lower haloalkenyl group, a lower alkyl group substituted with at least one member selected from the group consisting of halogen, cyano, lower alkoxy and lower alkoxycarbonyl, or a group of the formula: --COR 4 or --SO 2 R 4 in which R 4 is a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower cycloalkyl group, a lower haloalkenyl group, a lower alkyl group substituted with at least one member selected from the group consisting of halogen, cyano, lower alkoxy, lower cycloalkyl and phenoxy (phenoxy being optionally substituted with at least one halogen and/or at least one alkyl), a phenyl group, a furyl group, a thienyl group, a phenyl group substituted with at least one member selected from the group consisting of halogen, cyano, nitro, trifluoromethyl, lower alkyl and lower alkoxy, or an aralkyl group (aralkyl being optionally substituted with at least one halogen and/or at least one alkyl), with the proviso that when R 1 is methyl, R 2 is neither methyl nor butyl, and an inert carrier or diluent.
Claim 3
Dependent Claim
24 words
The fungicidal composition according to claim 1, which further comprises as an additional active ingredient(s) a benzimidazole thiophanate fungicide and/or a cyclic imide fungicide.
Claim 4
Dependent Claim
36 words
The fungicidal composition according to claim 2, wherein the benzimidazole thiophanate fungicide includes methyl 1-(butylcarbamoyl)benzimidazol-2-ylcarbamate, 2-(2-furyl)benzimidazole, 2-(4-thiazolyl)benzimidazole, methyl benzimidazol-2-ylcarbamate, 1,2-bis(3-methoxycarbonyl-2-thioureido)benzene, 1,2-bis(3-ethoxycarbonyl-2-thioureido)benzene, 2-(O,S-dimethylphosphorylamino)-1-(3'-methoxycarbonyl-2'-thioureido)benzene or 2-(O,O-dimethylthiophosphorylamino)-1-(3'-methoxycarbonyl-2'-thioureido)benzene and said cyclic imide fungicide includes 3-(3',5'-dichlorophenyl)-1,2-dimethylcyclopropane-1,2-dicarboximide, 3-(3',5'-dichlorophenyl)-1-isopropylcarbamoylimidazolidine-2,4-dione, 3-(3',5'-dichlorophenyl)-5-methyl-5-vinyloxazoline-2,4-dione or ethyl (RS)-3-(3',5'-dichlorophenyl)-5-methyl-2,4-dioxooxazolidine-5-carboxylate.
Claim 5
Dependent Claim
347 words
An N-phenylcarbamate of the formula: ##STR81## wherein R 1 and R 2 are, same or different, a lower alkyl group, a lower alkenyl group, a lower alkynyl group or a lower alkyl group substituted with at least one member selected from the group consisting of halogen, lower alkoxy and lower cycloalkyl; R 3 is a C 1 -C 8 alkyl group, a C 3 -C 8 alkenyl group, a C 3 -C 8 alkynyl group, lower cycloalkyl group, a lower haloalkenyl group, a lower haloalkynyl group, a lower aralkyl group, a lower alkyl group substituted with at least one member selected from the group consisting of halogen, cyano, lower alkoxy, lower alkenyloxy, lower haloalkoxy, phenoxy, lower aralkyloxy and lower cycloalkyl, or a group of the formula ##STR82## in which m is 0, 1 or 2, n is 1, 2 or 3; X and Y are, same or different, an oxygen atom or a sulfur atom; and Z is a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower cycloalkyl group, a lower haloalkenyl group, a lower alkyl group substituted with at least one member selected from the group consisting of halogen, cyano, lower alkoxy and lower alkoxycarbonyl, or a group of the formula: --COR 4 or --SO 2 R 4 in which R 4 is a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower cycloalkyl group, a lower haloalkenyl group, a lower alkyl group substituted with at least one member selected from the group consisting of halogen, cyano, lower alkoxy, lower cycloalkyl and phenoxy (phenoxy being optionally substituted with at least one halogen and/or at least one alkyl), a phenyl group, a furyl group, a thienyl group, a phenyl group substituted with at least one member selected from the group consisting of halogen, cyano, nitro, trifluoromethyl, lower alkyl and lower alkoxy, or an aralkyl group (aralkyl being optionally substituted with at least one halogen and/or at least one alkyl), with the proviso that when R 1 is methyl, R 2 is neither methyl nor butyl.
Claim 6
Dependent Claim
347 words
An N-phenylcarbamate of the formula: ##STR81## wherein R 1 and R 2 are, same or different, a lower alkyl group, a lower alkenyl group, a lower alkynyl group or a lower alkyl group substituted with at least one member selected from the group consisting of halogen, lower alkoxy and lower cycloalkyl; R 3 is a C 1 -C 8 alkyl group, a C 3 -C 8 alkenyl group, a C 3 -C 8 alkynyl group, lower cycloalkyl group, a lower haloalkenyl group, a lower haloalkynyl group, a lower aralkyl group, a lower alkyl group substituted with at least one member selected from the group consisting of halogen, cyano, lower alkoxy, lower alkenyloxy, lower haloalkoxy, phenoxy, lower aralkyloxy and lower cycloalkyl, or a group of the formula ##STR82## in which m is 0, 1 or 2, n is 1, 2 or 3; X and Y are, same or different, an oxygen atom or a sulfur atom; and Z is a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower cycloalkyl group, a lower haloalkenyl group, a lower alkyl group substituted with at least one member selected from the group consisting of halogen, cyano, lower alkoxy and lower alkoxycarbonyl, or a group of the formula: --COR 4 or --SO 2 R 4 in which R 4 is a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower cycloalkyl group, a lower haloalkenyl group, a lower alkyl group substituted with at least one member selected from the group consisting of halogen, cyano, lower alkoxy, lower cycloalkyl and phenoxy (phenoxy being optionally substituted with at least one halogen and/or at least one alkyl), a phenyl group, a furyl group, a thienyl group, a phenyl group substituted with at least one member selected from the group consisting of halogen, cyano, nitro, trifluoromethyl, lower alkyl and lower alkoxy, or an aralkyl group (aralkyl being optionally substituted with at least one halogen and/or at least one alkyl), with the proviso that when R 1 is methyl, R 2 is neither methyl nor butyl.
Claim 7
Dependent Claim
125 words
The N-phenylcarbamate according to claim 4, wherein R 1 and R 2 are independently methyl, ethyl, n-propyl, isopropyl, n-butyl, allyl, 2-butenyl, 3-butenyl, propargyl, 3-butynyl, difluoromethyl, 2-chloroethyl, 2,2,2-trifluoroethyl, 2-methoxyethyl or cyclopropylmethyl, R 3 is methyl, ethyl, n-propyl, isopropyl, sec-butyl, 1-ethylpropyl, 1-methylbutyl, 1-ethylbutyl, 2-butenyl, 3-butenyl, 2-methyl-2-propenyl, 1-ethyl-2-propenyl, 1-methyl-3-butenyl, 1-pentyl-2-propenyl, propargyl, 1-methyl-2-propynyl, 2-butynyl, 3-butynyl, 1-ethyl-2-propynyl, 1-methyl-3-butynyl, 1-butyl-2-propynyl, 1-pentyl-2-propynyl, cyclobutyl, cyclopentyl, 2-fluoroethyl, 2-chloroethyl, 2,2-dichloroethyl, 1-methyl-2-bromoethyl, 1-fluoromethyl-2-fluoroethyl, 1-bromoethyl-2-bromoethyl, 1-methyl-2,2,2-trichloroethyl, 1-ethyl-2-bromoethyl, 4-chloro-2-butenyl, 4-chloro-2-butynyl, 2-cyanoethyl, 1-methyl-2-methoxyethyl, 1-methyl-2-butoxyethyl, 2-allyloxyethyl, 2-(2-chloroethoxy)ethyl, 2-benzyloxyethyl, 1-chloromethyl-2-methoxyethyl, cyclopropylmethyl, 1-cyclopropylethyl, 1-cyclopentylethyl, 2-furylmethyl, 1-phenylethyl or 3-tetrahydrofuranyl; X and Y are independently oxygen or sulfur; and Z is hydrogen, methyl, ethyl, n-butyl, allyl, acetyl, propionyl, n-pentanoyl, sec-pentanoyl, cyclopropanecarbonyl, benzoyl, 2-chlorobenzoyl, 2,4-dichlorobenzoyl, 4-methylbenzoyl, methanesulfonyl or ethoxycarbonylmethyl, with the proviso that when R 1 is methyl, R 2 is neither methyl nor butyl.
Claim 8
Dependent Claim
83 words
The N-phenylcarbamate according to claim 5, wherein R 1 and R 2 are independently methyl, ethyl, n-propyl, allyl or propargyl, R 3 is ethyl, isopropyl, sec-butyl, 1-methylbutyl, 1-ethylpropyl, 1-ethylbutyl, 1-methyl-2-propenyl, 1-ethyl-2-propenyl, 1-methyl-3-butenyl, propargyl, 1-methyl-2-propynyl, 1-ethyl-2-propynyl, 3-butynyl, 1-methyl-3-butynyl, 1-butyl-2-propynyl, 2-fluoroethyl, 1-methyl-2-bromoethyl, 1-fluoromethyl-2-fluoroethyl, 1-bromomethyl-2-bromoethyl, 4-chloro-2-butynyl, 1-methyl-2-methoxyethyl, 1-cyclopropylethyl or 1-phenylethyl; X is oxygen, Y is oxygen or sulfur; and Z is hydrogen, acetyl, propionyl, n-pentanoyl, sec-pentanoyl, cyclopropanecarbonyl, benzoyl, 2-chlorobenzoyl, 2,4-dichlorobenzoyl or 4-methylbenzoyl, with the proviso that when R 1 is methyl, R 2 is not methyl.
Claim 9
Dependent Claim
44 words
The N-phenylcarbamate according to claim 6, wherein R 1 and R 2 are ethyl, R 3 is ethyl, isopropyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, 1-methyl-3-butenyl, 1-methyl-2-propynyl, 4-chloro-2-butynyl or 1-phenylethyl, X is oxygen, Y is oxygen or sulfur and Z is hydrogen, acetyl, cyclopropanecarbonyl, benzoyl or 2-chlorobenzoyl.
Claim 10
Dependent Claim
8 words
The N-phenylcarbamate according to claim 4, Isopropyl N-(3,4-diethoxyphenyl)carbamate.
Claim 11
Dependent Claim
8 words
The N-phenylcarbamate according to claim 4, 1-Methyl-2-propynyl N-(3,4-diethoxyphenyl)-carbamate.
Claim 12
Dependent Claim
8 words
The N-phenylcarbamate according to claim 4, 4-Chloro-2-butynyl N-(3,4-diethoxyphenyl)-carbamate.
Claim 13
Dependent Claim
8 words
The N-phenylcarbamate according to claim 4, Isopropyl N-(3,4-diethoxyphenyl)thiolcarbamate.
Claim 14
Dependent Claim
8 words
The N-phenylcarbamate according to claim 4, 1-Phenylethyl N-(3,4-diethoxyphenyl)carbamate.
Claim 15
Dependent Claim
8 words
The N-phenylcarbamate according to claim 4, Isopropyl N-acetyl-N-(3,4-diethoxyphenyl)-carbamate.
Claim 16
Dependent Claim
8 words
The N-phenylcarbamate according to claim 4, Isopropyl N-cyclopropanecarbonyl-N-(3,4-diethoxyphenyl)carbamate.
Claim 17
Dependent Claim
8 words
The N-phenylcarbamate according to claim 4, Isopropyl N-benzony-N-(3,4-diethoxyphenyl)-carbamate.
Claim 18
Dependent Claim
8 words
The N-phenylcarbamate according to claim 4, Isopropyl N-(2-chlorobenzoyl)-N-(3,4-diethoxyphenyl)carbamate.
Claim 19
Dependent Claim
50 words
A method for controlling plant pathogenic fungi which comprises applying a fungicidally effective amount of at least one of the N-phenylcarbamates of the formula: ##STR83## wherein R 1 , R 2 , R 3 , X, Y and Z are each as defined in claim 1, to plant pathogenic fungi.
Claim 20
Dependent Claim
15 words
The method according to claim 17, wherein the plant pathogenic fungi is the drug-resistant strain.
Claim 21
Dependent Claim
55 words
A method for controlling plant pathogenic fungi which comprises applying a fungicidally effective amount of a mixture of the N-phenylcarbamate of the formula: ##STR84## wherein R 1 , R 2 , R 3 , X, Y and Z are each as defined in claim 1 and a benzimidazole thiophanate fungicide and/or a cyclic imide fungicide.
Claim 22
Dependent Claim
86 words
A process for producing an N-phenylcarbamate of the formula: ##STR85## wherein Z is as defined in claim 4 except hydrogen and R 1 , R 2 , R 3 , X and Y are each as defined in claim 4, which comprises reacting a 3,4-dialkoxyphenylcarbamate of the formula: ##STR86## wherein R 1 , R 2 , R 3 , X and Y are each as defined above, with a halide of the formula: A--Z wherein A is a halogen atom and Z is as defined above.
Claim 23
Dependent Claim
343 words
A fungicidal composition which comprises as an active ingredient a fungicidally effective amount of an N-phenylcarbamate of the formula: ##STR87## wherein R 1 and R 2 are, same or different, a lower alkyl group, a lower alkenyl group, a lower alkynyl group or a lower alkyl group substituted with at least one member selected from the group consisting of halogen, lower alkoxy and lower cycloalkyl; R 3 is a C 1 -C 8 alkyl group, a C 3 -C 8 alkenyl group, a C 3 -C 8 alkynyl group, lower cycloalkyl group, a lower haloalkenyl group, a lower haloalkynyl group, a lower aralkyl group, a lower alkyl group substituted with at least one member selected from the group consisting of halogen, cyano, lower alkoxy, lower alkenyloxy, lower haloalkoxy, phenoxy, lower aralkyloxy and lower cycloalkyl; X and Y are, same or different, an oxygen atom or a sulfur atom; and Z is a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower cycloalkyl group, a lower haloalkenyl group, a lower alkyl group substituted with at least one member selected from the group consisting of halogen, cyano, lower alkoxy and lower alkoxycarbonyl, or a group of the formula: --COR 4 or --SO 2 R 4 in which R 4 is a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower cycloalkyl group, a lower haloalkenyl group, a lower alkyl group substituted with at least one member selected from the group consisting of halogen, cyano, lower alkoxy, lower cycloalkyl and phenoxy (phenoxy being optionally substituted with at least one halogen and/or at least one alkyl), a phenyl group, a furyl group, a phenyl group substituted with at least one member selected from the group consisting of halogen, cyano, nitro, trifluoromethyl, lower alkyl and lower alkoxy, or an aralkyl group (aralkyl being optionally substituted with at least one halogen and/or at least one alkyl), with the proviso that when R 1 is methyl, R 2 is neither methyl nor butyl, and an inert carrier or diluent.
Claim 24
Dependent Claim
343 words
A fungicidal composition which comprises as an active ingredient a fungicidally effective amount of an N-phenylcarbamate of the formula: ##STR87## wherein R 1 and R 2 are, same or different, a lower alkyl group, a lower alkenyl group, a lower alkynyl group or a lower alkyl group substituted with at least one member selected from the group consisting of halogen, lower alkoxy and lower cycloalkyl; R 3 is a C 1 -C 8 alkyl group, a C 3 -C 8 alkenyl group, a C 3 -C 8 alkynyl group, lower cycloalkyl group, a lower haloalkenyl group, a lower haloalkynyl group, a lower aralkyl group, a lower alkyl group substituted with at least one member selected from the group consisting of halogen, cyano, lower alkoxy, lower alkenyloxy, lower haloalkoxy, phenoxy, lower aralkyloxy and lower cycloalkyl; X and Y are, same or different, an oxygen atom or a sulfur atom; and Z is a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower cycloalkyl group, a lower haloalkenyl group, a lower alkyl group substituted with at least one member selected from the group consisting of halogen, cyano, lower alkoxy and lower alkoxycarbonyl, or a group of the formula: --COR 4 or --SO 2 R 4 in which R 4 is a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower cycloalkyl group, a lower haloalkenyl group, a lower alkyl group substituted with at least one member selected from the group consisting of halogen, cyano, lower alkoxy, lower cycloalkyl and phenoxy (phenoxy being optionally substituted with at least one halogen and/or at least one alkyl), a phenyl group, a furyl group, a phenyl group substituted with at least one member selected from the group consisting of halogen, cyano, nitro, trifluoromethyl, lower alkyl and lower alkoxy, or an aralkyl group (aralkyl being optionally substituted with at least one halogen and/or at least one alkyl), with the proviso that when R 1 is methyl, R 2 is neither methyl nor butyl, and an inert carrier or diluent.
Claim 25
Dependent Claim
24 words
The fungicidal composition according to claim 21, which further comprises as an additional active ingredient(s) a benzimidazole thiophanate fungicide and/or a cyclic imide fungicide.
Claim 26
Dependent Claim
29 words
The fungicidal composition according to claim 22, wherein the benzimidazole thiophanate fungicide includes methyl 1-(butylcarbamoyl)benzimidazol-2-ylcarbamate, 2-(2-furyl)benzimidazole, methyl benzimidazol-2-ylcarbamate, and said cyclic imide fungicide includes 3-(3',5'-dichlorophenyl)-1,2-dimethylcyclopropane-1,2-dicarboximide, 3-(3',5'-dichlorophenyl)-1-isopropylcarbamoylimidazolidine-2,4-dione, 3-(3',5'-dichlorophenyl)-5methyl-5-vinyloxazoline-2,4-dione or ethyl(RS)-3-(3',5'-dichlorophenyl)-5-methyl-2,4-dioxooxazolidine-5-carboxylate.
Claim 27
Dependent Claim
324 words
An N-phenylcarbamate of the formula: ##STR88## wherein R 1 and R 2 are, same or different, a lower alkyl group, a lower alkenyl group, a lower alkynyl group or a lower alkyl group substituted with at least one member selected from the group consisting of halogen, lower alkoxy and lower cycloalkyl; R 3 is a C 1 -C 8 alkyl group, a C 3 -C 8 alkenyl group, a C 3 -C 8 alkynyl group, lower cycloalkyl group, a lower haloalkenyl group, a lower haloalkynyl group, a lower aralkyl group, a lower alkyl group substituted with at least one member selected from the group consisting of halogen, cyano, lower alkoxy, lower alkenyloxy, lower haloalkoxy, phenoxy, lower aralkyloxy and lower cycloalkyl; X and Y are, same or different, an oxygen atom or a sulfur atom; and Z is a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower cycloalkyl group, a lower haloalkenyl group, a lower alkyl group substituted with at least one member selected from the group consisting of halogen, cyano, lower alkoxy and lower alkoxycarbonyl, or a group of the formula: --COR 4 or -- SO 2 R 4 in which R 4 is a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower cycloalkyl group, a lower haloalkenyl group, a lower alkyl group substituted with at least one member selected from the group consisting of halogen, cyano, lower alkoxy, lower cycloalkyl and phenoxy (phenoxy being optionally substituted with at least one halogen and/or at least one alkyl), a phenyl group, a furyl group, a phenyl group substituted with at least one member selected from the group consisting of halogen, cyano, nitro, trifluoromethyl, lower alkyl and lower alkoxy, or an aralkyl group (aralkyl being optionally substituted with at least one halogen and/or at least one alkyl), with the proviso that when R 1 is methyl, R 2 is neither methyl nor butyl.
Claim 28
Dependent Claim
324 words
An N-phenylcarbamate of the formula: ##STR88## wherein R 1 and R 2 are, same or different, a lower alkyl group, a lower alkenyl group, a lower alkynyl group or a lower alkyl group substituted with at least one member selected from the group consisting of halogen, lower alkoxy and lower cycloalkyl; R 3 is a C 1 -C 8 alkyl group, a C 3 -C 8 alkenyl group, a C 3 -C 8 alkynyl group, lower cycloalkyl group, a lower haloalkenyl group, a lower haloalkynyl group, a lower aralkyl group, a lower alkyl group substituted with at least one member selected from the group consisting of halogen, cyano, lower alkoxy, lower alkenyloxy, lower haloalkoxy, phenoxy, lower aralkyloxy and lower cycloalkyl; X and Y are, same or different, an oxygen atom or a sulfur atom; and Z is a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower cycloalkyl group, a lower haloalkenyl group, a lower alkyl group substituted with at least one member selected from the group consisting of halogen, cyano, lower alkoxy and lower alkoxycarbonyl, or a group of the formula: --COR 4 or -- SO 2 R 4 in which R 4 is a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower cycloalkyl group, a lower haloalkenyl group, a lower alkyl group substituted with at least one member selected from the group consisting of halogen, cyano, lower alkoxy, lower cycloalkyl and phenoxy (phenoxy being optionally substituted with at least one halogen and/or at least one alkyl), a phenyl group, a furyl group, a phenyl group substituted with at least one member selected from the group consisting of halogen, cyano, nitro, trifluoromethyl, lower alkyl and lower alkoxy, or an aralkyl group (aralkyl being optionally substituted with at least one halogen and/or at least one alkyl), with the proviso that when R 1 is methyl, R 2 is neither methyl nor butyl.
Claim 29
Dependent Claim
125 words
The N-phenylcarbamate according to claim 24, wherein R 1 and R 2 are independently methyl, ethyl, n-propyl, isopropyl, n-butyl, allyl, 2-butenyl, 3-butenyl, propargyl, 3-butynyl, difluoromethyl, 2-chloroethyl, 2,2,2-trifluoroethyl, 2-methoxyethyl or cyclopropylmethyl, R 3 is methyl, ethyl, n-propyl, isopropyl, sec-butyl, 1-ethylpropyl, 1-methylbutyl, 1-ethylbutyl, 2-butenyl, 3-butenyl, 2-methyl-2-propenyl, 1-ethyl-2-propenyl, 1-methyl-3-butenyl, 1-pentyl-2-propenyl, propargyl, 1-methyl-2-propynyl, 2-butynyl, 3-butynyl, 1-ethyl-2-propynyl, 1-methyl-3-butynyl, 1-butyl-2-propynyl, 1-pentyl-2-propynyl, cyclobutyl, cyclopentyl, 2-fluoroethyl, 2-chloroethyl, 2,2-dichloroethyl, 1-methyl-2-bromoethyl, 1-fluoromethyl-2-fluoroethyl, 1-bromomethyl-2bromoethyl, 1-methyl-2,2,2-trichloroethyl, 1-ethyl-2-bromoethyl, 4-chloro-2-butenyl, 4-chloro-2-butynyl, 2-cyanoethyl, 1-methyl-2-methoxyethyl, 1-methyl-2-butoxyethyl, 2-allyloxyethyl, 2-(2-chloroethoxy)ethyl, 2-benzyloxyethyl, 1-chloromethyl-2-methoxyethyl, cyclopropylmethyl, 1-cyclopropylethyl, 1-cyclopentylethyl, 2-furylmethyl, 1-phenylethyl or 3-tetrahydrofuranyl; X and Y are independently oxygen or sulfur; and z is hydrogen, methyl, ethyl, n-butyl, allyl, acetyl, propionyl, n-pentanoyl, sec-pentanoyl, cyclopropanecarbonyl, benzoyl, 2-chlorobenzoyl, 2,4-dichlorobenzoyl, 4-methylbenzoyl, methanesulfonyl or ethoxycarbonylmethyl, with the proviso that when R 1 is methyl, R 2 is neither methyl nor butyl.
Claim 30
Dependent Claim
83 words
The N-phenylcarbamate according to claim 25, wherein R 1 and R 2 are independently methyl, ethyl, n-propyl, allyl or propargyl, R 3 is ethyl, isopropyl, sec-butyl, 1-methylbutyl, 1-ethylpropyl, 1-ethylbutyl, 1-methyl-2-propenyl, 1-ethyl-2-propenyl, 1-methyl-3-butenyl, propargyl, 1-methyl-2-propynyl, 1-ethyl-2-propynyl, 3-butynyl, 1-methyl-3-butynyl, 1-butyl-2-propynyl, 2-fluoroethyl, 1-methyl-2-bromoethyl, 1-fluoromethyl-2-fluoroethyl, 1-bromomethyl-2-bromoethyl, 4-chloro-2-butynyl, 1-methyl-2-methoxyethyl, 1-cyclopropylethyl or 1-phenylethyl; X is oxygen, Y is oxygen or sulfur; and Z is hydrogen, acetyl, propionyl, n-pentanoyl, sec-pentanoyl, cyclopropanecarbonyl, benzoyl, 2-chlorobenzoyl, 2,4-dichlorobenzoyl, or 4-methylbenzoyl, with the proviso that when R 1 is methyl, R 2 is not methyl.
Claim 31
Dependent Claim
44 words
The N-phenylcarbamate according to claim 26, wherein R 1 and R 2 are ethyl, R 3 is ethyl, isopropyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, 1-methyl-3-butenyl, 1-methyl-2-propynyl, 4-chloro-2-butynyl or 1-phenylethyl, X is oxygen, Y is oxygen or sulfur and Z is hydrogen, acetyl, cyclopropanecarbonyl, benzoyl or 2-chlorobenzoyl.
Claim 32
Dependent Claim
8 words
The N-phenylcarbamate according to claim 24, Isopropyl N-(3,4-diethoxyphenyl)carbamate.
Claim 33
Dependent Claim
8 words
The N-phenylcarbamate according to claim 24, 1-Methyl-2-propynyl N-(3,4-diethoxyphenyl)carbamate.
Claim 34
Dependent Claim
8 words
The N-phenylcarbamate according to claim 24, 4-Chloro-2-butynyl N-(3,4-diethoxyphenyl)carbamate.
Claim 35
Dependent Claim
8 words
The N-phenylcarbamate according to claim 24, Isopropyl N-(3,4-diethoxyphenyl)thiolcarbamate.
Claim 36
Dependent Claim
8 words
The N-phenylcarbamate according to claim 24, 1-Phenylethyl N-(3,4-diethoxyphenyl)carbamate.
Claim 37
Dependent Claim
8 words
The N-phenylcarbamate according to claim 24, Isopropyl N-acetyl-N-(3,4-diethoxyphenyl)carbamate.
Claim 38
Dependent Claim
8 words
The N-phenylcarbamate according to claim 24, Isopropyl N-cyclopropanecarbonyl-N-(3,4-diethoxyphenyl)carbamate.
Claim 39
Dependent Claim
8 words
The N-phenylcarbamate according to claim 24, Isopropyl N-benzony-N-(3,4-diethoxyphenyl)carbamate.
Claim 40
Dependent Claim
8 words
The N-phenylcarbamate according to claim 24, Isopropyl N-(2-chlorobenzoyl)-N-(3,4-diethoxyphenyl)carbamate.
Claim 41
Dependent Claim
50 words
A method for controlling plant pathogenic fungi which comprises applying a fungicidally effective amount of at least one of the N-phenylcarbamates of the formula: ##STR89## wherein R 1 , R 2 , R 3 , X, Y and Z are each as defined in claim 21, to plant pathogenic fungi.
Claim 42
Dependent Claim
15 words
The method according to claim 37, wherein the plant pathogenic fungi is the drug-resistant strain.
Claim 43
Dependent Claim
54 words
A method for controlling plant pathogenic fungi which comprises applying a fungicidally effective amount of a mixture of the N-phenylcarbamate of the formula: ##STR90## wherein R 1 R 2 , R 3 , X, Y and Z are each as defined in claim 21, and a benzimidazole thiophanate fungicide and/or a cyclic imide fungicide.
Claim 44
Dependent Claim
8 words
The n-phenylcarbamate according to claim 24, ethyl N-(3,4-diethoxyphenyl)carbamate.
Claim 45
Dependent Claim
13 words
A fungicidal composition according to claim 21, wherein said n-phenylcarbamate is ethyl N-(3,4-diethoxyphenyl)carbamate.
Claim 46
Dependent Claim
17 words
A method for controlling plant pathogenic fungi according to claim 37, wherein said n-phenylcarbamate is ethyl N-(3,4-diethoxyphenyl)carbamate.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1989-08-25 | 1990-02-24 | 1990-08-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-08-25 | 1994-02-24 | 1994-08-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-08-25 | 1998-02-24 | 1998-08-26 | $7700.00 | Window Closed / Lapsed |