US4381195A
Expired / Lapsed
US
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N-Methylcarbamoyloxy anilides as herbicide extenders
Assignee: Zeneca Inc
•
Filing: 1981-04-20
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Granted: 1983-04-26
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Expires: 2001-04-20
Abstract
Abstract Herbicidally active thiolcarbamates are employed in combination with certain N-methylcarbamoyloxy anilides having the formula <IMAGE> in which R4 is selected from the group consisting of hydrogen and carbethoxymethyl, R5 is selected from the group consisting of C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy, C3-C6 cycloalkyl, C3-C5 alkanoylmethyl, C1-C3 alkylamino, C1-C3 dialkylamino, carbamylthiomethyl, and C2-C4 carbalkoxyamino, R6 is selected from the group consisting of C1-C3 alkyl, C2-C4 alkanoylamino, and halogen, X is selected from the group consisting of oxygen and sulfur, and n is zero or one. In a typical application, the isonitrile is included in sufficient quantity to lessen the rate of soil degradation of the thiolcarbamate. As a result, the herbicidal effectiveness of the thiolcarbamate is enhanced and prolonged, rendering a single application of the herbicide effective over a longer period of time.
Inventors
- 👤 Daniel L. Hyzak
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 09:28
CPC Classifications
A; A01; A01N; A01N47/00; A01N47/08; A01N47/28; A01N47/34; A01N25/00; A01N25/22; A01N47/10; A01N47/12; A01N47/22; A01N47/30
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
186 words
An herbicidal composition of extended soil life comprising (a) an herbicidally effective amount of a thiolcarbamate having the formula ##STR19## in which R 1 , R 2 , and R 3 are independently C 2 -C 4 alkyl; and (b) an amount of N-methylcarbamoyloxy anilide sufficient to extend the soil life of said thiolcarbamate, said N-methylcarbamoyloxy anilide having the formula ##STR20## in which R 4 is selected from the group consisting of hydrogen and carbethoxymethyl, R 5 is selected from the group consisting of C 1 -C 6 alkyl, halogenated C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 3 -C 6 cycloalkyl, C 3 -C 5 alkanoylmethyl, C 1 -C 3 alkylamino, C 1 -C 3 dialkyl-amino, carbamylthiomethyl, and C 2 -C 4 carbalkoxyamino, R 6 is selected from the group consisting of C 1 -C 3 alkyl, C 2 -C 4 alkanoylamino, and halogen, X is selected from the group consisting of oxygen and sulfur, and n is zero or one, wherein the weight ratio of (a) to (b) ranges from about 1:1 to about 5:1, and (c) an inert diluent carrier.
Claim 2
Dependent Claim
186 words
An herbicidal composition of extended soil life comprising (a) an herbicidally effective amount of a thiolcarbamate having the formula ##STR19## in which R 1 , R 2 , and R 3 are independently C 2 -C 4 alkyl; and (b) an amount of N-methylcarbamoyloxy anilide sufficient to extend the soil life of said thiolcarbamate, said N-methylcarbamoyloxy anilide having the formula ##STR20## in which R 4 is selected from the group consisting of hydrogen and carbethoxymethyl, R 5 is selected from the group consisting of C 1 -C 6 alkyl, halogenated C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 3 -C 6 cycloalkyl, C 3 -C 5 alkanoylmethyl, C 1 -C 3 alkylamino, C 1 -C 3 dialkyl-amino, carbamylthiomethyl, and C 2 -C 4 carbalkoxyamino, R 6 is selected from the group consisting of C 1 -C 3 alkyl, C 2 -C 4 alkanoylamino, and halogen, X is selected from the group consisting of oxygen and sulfur, and n is zero or one, wherein the weight ratio of (a) to (b) ranges from about 1:1 to about 5:1, and (c) an inert diluent carrier.
Claim 3
Dependent Claim
135 words
An herbicide composition of extended soil life comprising an herbicidally effective amount of S-ethyl N,N-di-n-propylthiolcarbamate and an amount of an N-methylcarbamoyloxy anilide sufficient to extend the soil life of said thiolcarbamate, said N-methylcarbamoyloxy anilide having the formula ##STR21## in which R 4 is selected from the group consisting of hydrogen and carbethoxymethyl, R 5 is selected from the group consisting of C 1 -C 4 alkyl, dichloromethyl, bromomethyl, dibromoethyl, butoxy, cyclobutyl, acetonyl, methylamino, dimethylamino, carbamylthiomethyl, and carbethoxyamino, R 6 is selected from the group consisting of methyl, propionylamino, and bromine, X is selected from the group consisting of oxygen and sulfur, and n is zero or one, wherein the weight ratio of said S-ethyl N,N-di-n-propylthiolcarbamate to said N-methoxycarbamoyloxy anilide ranges from about 1:1 to about 5:1, and which composition additionally includes an inert diluent carrier.
Claim 4
Dependent Claim
135 words
An herbicide composition of extended soil life comprising an herbicidally effective amount of S-ethyl N,N-di-n-propylthiolcarbamate and an amount of an N-methylcarbamoyloxy anilide sufficient to extend the soil life of said thiolcarbamate, said N-methylcarbamoyloxy anilide having the formula ##STR21## in which R 4 is selected from the group consisting of hydrogen and carbethoxymethyl, R 5 is selected from the group consisting of C 1 -C 4 alkyl, dichloromethyl, bromomethyl, dibromoethyl, butoxy, cyclobutyl, acetonyl, methylamino, dimethylamino, carbamylthiomethyl, and carbethoxyamino, R 6 is selected from the group consisting of methyl, propionylamino, and bromine, X is selected from the group consisting of oxygen and sulfur, and n is zero or one, wherein the weight ratio of said S-ethyl N,N-di-n-propylthiolcarbamate to said N-methoxycarbamoyloxy anilide ranges from about 1:1 to about 5:1, and which composition additionally includes an inert diluent carrier.
Claim 5
Dependent Claim
15 words
A composition according to claim 2 in which said N-methylcarbamoyloxy anilide has the formula ##STR22##
Claim 6
Dependent Claim
15 words
A composition according to claim 2 in which said N-methylcarbamoyloxy anilide has the formula ##STR23##
Claim 7
Dependent Claim
15 words
A composition according to claim 2 in which said N-methylcarbamoyloxy anilide has the formula ##STR24##
Claim 8
Independent Claim
190 words
A method of controlling undesirable vegetation which comprises applying to the locus where control is desired both (a) an herbicidally effective amount of a thiolcarbamate having the formula ##STR25## in which R 1 , R 2 , and R 3 are independently C 2 -C 4 alkyl; and (b) an amount of an N-methylcarbamoyloxy anilide sufficient to extend the soil life of said thiolcarbamate, said N-methylcarbamoyloxy anilide having the formula ##STR26## in which R 4 is selected from the group consisting of hydrogen and carbethoxymethyl, R 5 is selected from the group consisting of C 1 -C 6 alkyl, halogenated C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 3 -C 6 cycloalkyl, C 3 -C 5 alkanoylmethyl, C 1 -C 3 alkylamino, C 1 -C 3 dialkyl-amino, carbamylthiomethyl, and C 2 -C 4 carbalkoxyamino, R 6 is selected from the group consisting of C 1 -C 3 alkyl, C 2 -C 4 alkanoylamino, and halogen, X is selected from the group consisting of oxygen and sulfur, and n is zero or one, wherein the weight ratio of (a) to (b) ranges from about 1:1 to about 5:1.
Claim 9
Independent Claim
190 words
A method of controlling undesirable vegetation which comprises applying to the locus where control is desired both (a) an herbicidally effective amount of a thiolcarbamate having the formula ##STR25## in which R 1 , R 2 , and R 3 are independently C 2 -C 4 alkyl; and (b) an amount of an N-methylcarbamoyloxy anilide sufficient to extend the soil life of said thiolcarbamate, said N-methylcarbamoyloxy anilide having the formula ##STR26## in which R 4 is selected from the group consisting of hydrogen and carbethoxymethyl, R 5 is selected from the group consisting of C 1 -C 6 alkyl, halogenated C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 3 -C 6 cycloalkyl, C 3 -C 5 alkanoylmethyl, C 1 -C 3 alkylamino, C 1 -C 3 dialkyl-amino, carbamylthiomethyl, and C 2 -C 4 carbalkoxyamino, R 6 is selected from the group consisting of C 1 -C 3 alkyl, C 2 -C 4 alkanoylamino, and halogen, X is selected from the group consisting of oxygen and sulfur, and n is zero or one, wherein the weight ratio of (a) to (b) ranges from about 1:1 to about 5:1.
Claim 10
Independent Claim
135 words
A method of controlling undesirable vegetation which comprises applying to the locus where control is desired both an herbicidally effective amount of S-ethyl N,N-di-n-propylthiolcarbamate and an amount of an N-methylcarbamoyloxy anilide sufficient to extend the soil life of said thiolcarbamate, said N-methylcarbamoyloxy anilide having the formula ##STR27## in which R 4 is selected from the group consisting of hydrogen and carbethoxymethyl, R 5 is selected from the group consisting of C 1 -C 4 alkyl, dichloromethyl, bromomethyl, dibromoethyl, butoxy, cyclobutyl, acetonyl, methylamino, dimethylamino, carbamylthiomethyl, and carbethoxyamino, R 6 is selected from the group consisting of methyl, propionylamino, and bromine, X is selected from the group consisting of oxygen and sulfur, and n is zero or one, wherein the weight ratio of said S-ethyl N,N-di-n-propylthiolcarbamate and said N-methylcarbamoyloxy anilide ranges from about 1:1 to about 5:1.
Claim 11
Independent Claim
135 words
A method of controlling undesirable vegetation which comprises applying to the locus where control is desired both an herbicidally effective amount of S-ethyl N,N-di-n-propylthiolcarbamate and an amount of an N-methylcarbamoyloxy anilide sufficient to extend the soil life of said thiolcarbamate, said N-methylcarbamoyloxy anilide having the formula ##STR27## in which R 4 is selected from the group consisting of hydrogen and carbethoxymethyl, R 5 is selected from the group consisting of C 1 -C 4 alkyl, dichloromethyl, bromomethyl, dibromoethyl, butoxy, cyclobutyl, acetonyl, methylamino, dimethylamino, carbamylthiomethyl, and carbethoxyamino, R 6 is selected from the group consisting of methyl, propionylamino, and bromine, X is selected from the group consisting of oxygen and sulfur, and n is zero or one, wherein the weight ratio of said S-ethyl N,N-di-n-propylthiolcarbamate and said N-methylcarbamoyloxy anilide ranges from about 1:1 to about 5:1.
Claim 12
Dependent Claim
15 words
A method according to claim 7 in which said N-methylcarbamoyloxy anilide has the formula ##STR28##
Claim 13
Dependent Claim
15 words
A method according to claim 7 in which said N-methylcarbamoyloxy anilide has the formula ##STR29##
Claim 14
Dependent Claim
15 words
A method according to claim 7 in which said N-methylcarbamoyloxy anilide has the formula ##STR30##
Claim 15
Independent Claim
183 words
A method of extending the soil life of a thiolcarbamate having the formula ##STR31## in which R 1 , R 2 , and R 3 are independently C 2 -C 4 alkyl; which comprises applying to the soil containing said thiolcarbamate or to which said thiolcarbamate is to be applied an effective amount of an N-methylcarbamoyloxy anilide having the formula ##STR32## in which R 4 is selected from the group consisting of hydrogen and carbethoxymethyl, R 5 is selected from the group consisting of C 1 -C 6 alkyl, halogenated C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 3 -C 6 cycloalkyl, C 3 -C 5 alkanoylmethyl, C 1 -C 3 alkylamino, C 1 -C 3 dialkyl-amino, carbamylthiomethyl, and C 2 -C 4 carbalkoxyamino, R 6 is selected from the group consisting of C 1 -C 3 alkyl, C 2 -C 4 alkanoylamino, and halogen, X is selected from the group consisting of oxygen and sulfur, and n is zero or one, wherein the weight ratio of said thiolcarbamate to said N-methylcarbamoyloxy anilide ranges from about 1:1 to about 5:1.
Claim 16
Independent Claim
183 words
A method of extending the soil life of a thiolcarbamate having the formula ##STR31## in which R 1 , R 2 , and R 3 are independently C 2 -C 4 alkyl; which comprises applying to the soil containing said thiolcarbamate or to which said thiolcarbamate is to be applied an effective amount of an N-methylcarbamoyloxy anilide having the formula ##STR32## in which R 4 is selected from the group consisting of hydrogen and carbethoxymethyl, R 5 is selected from the group consisting of C 1 -C 6 alkyl, halogenated C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 3 -C 6 cycloalkyl, C 3 -C 5 alkanoylmethyl, C 1 -C 3 alkylamino, C 1 -C 3 dialkyl-amino, carbamylthiomethyl, and C 2 -C 4 carbalkoxyamino, R 6 is selected from the group consisting of C 1 -C 3 alkyl, C 2 -C 4 alkanoylamino, and halogen, X is selected from the group consisting of oxygen and sulfur, and n is zero or one, wherein the weight ratio of said thiolcarbamate to said N-methylcarbamoyloxy anilide ranges from about 1:1 to about 5:1.
Claim 17
Independent Claim
127 words
A method of extending the soil life of S-ethyl N,N-di-npropylthiolcarbamate which comprises applying to the soil containing said thiolcarbamate or to which said thiolcarbamate is to be applied an effective amount of an N-methylcarbamoyloxy anilide having the formula ##STR33## in which R 4 is selected from the group consisting of hydrogen and carbethoxymethyl, R 5 is selected from the group consisting of C 1 -C 4 alkyl, dichloromethyl, bromomethyl, dibromoethyl, butoxy, cyclobutyl, acetonyl, methylamino, dimethylamino, carbamylthiomethyl, and carbethoxyamino, R 6 is selected from the group consisting of methyl, propionylamino, and bromine, X is selected from the group consisting of oxygen and sulfur, and n is zero or one, wherein the weight ratio of said S-ethyl N,N-di-n-propylthiolcarbamate to said N-methylcarbamoyloxy anilide ranges from about 1:1 to about 5:1.
Claim 18
Independent Claim
127 words
A method of extending the soil life of S-ethyl N,N-di-npropylthiolcarbamate which comprises applying to the soil containing said thiolcarbamate or to which said thiolcarbamate is to be applied an effective amount of an N-methylcarbamoyloxy anilide having the formula ##STR33## in which R 4 is selected from the group consisting of hydrogen and carbethoxymethyl, R 5 is selected from the group consisting of C 1 -C 4 alkyl, dichloromethyl, bromomethyl, dibromoethyl, butoxy, cyclobutyl, acetonyl, methylamino, dimethylamino, carbamylthiomethyl, and carbethoxyamino, R 6 is selected from the group consisting of methyl, propionylamino, and bromine, X is selected from the group consisting of oxygen and sulfur, and n is zero or one, wherein the weight ratio of said S-ethyl N,N-di-n-propylthiolcarbamate to said N-methylcarbamoyloxy anilide ranges from about 1:1 to about 5:1.
Claim 19
Dependent Claim
15 words
A method according to claim 12 in which said N-methylcarbamoyloxy anilide has the formula ##STR34##
Claim 20
Dependent Claim
15 words
A method according to claim 12 in which said N-methylcarbamoyloxy anilide has the formula ##STR35##
Claim 21
Dependent Claim
15 words
A method according to claim 12 in which said N-methylcarbamoyloxy anilide has the formula ##STR36##
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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) | 1986-04-25 | 1986-10-25 | 1987-04-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-04-25 | 1990-10-25 | 1991-04-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-04-25 | 1994-10-25 | 1995-04-26 | $7700.00 | Window Closed / Lapsed |