US4163787A
Expired / Lapsed
US
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Substituted pyridine methyl esters of cyclopropane carboxylic acids and their use as insecticides
Assignee: Dow Chemical Co
•
Filing: 1977-12-12
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Granted: 1979-08-07
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Expires: 1997-12-12
Abstract
Abstract Substituted pyridine methyl esters of cyclopropane carboxylic acids and the geometric and optical isomers thereof are prepared which correspond to the formula: ##STR1## wherein X independently represents alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, alkylsulfonyl of 1 to 4 carbon atoms, trifluoromethyl, 3,4-methylenedioxy, chloro, fluoro or bromo; n represents an integer of 0 to 2; Y represents oxygen or sulfur; R represents hydrogen, cyano or ethynyl and Z represents chloro, fluoro or bromo. These compounds have been found to exhibit a high degree of insecticidal activity and compositions containing said compounds are so employed.
Inventors
- 👤 Sudarshan K. Malhotra
- 👤 Michael J. Ricks
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 15:28
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/62; C07D213/63; C07D213/64; C07D213/647; A; A01; A01N; A01N53/00; C07D213/70
Claims Analysis
Total Claims: 48
Claim 1
Independent Claim
71 words
A compound corresponding to the formula ##STR28## wherein X independently represents alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, alkylsulfonyl of 1 to 4 carbon atoms, trifluoromethyl, 3,4-methylenedioxy, chloro, fluoro or bromo; n represents an integer of 0 to 2; Y represents oxygen or sulfur; R represents hydrogen, cyano or ethynyl and Z represents chloro, fluoro or bromo.
Claim 2
Dependent Claim
71 words
A compound corresponding to the formula ##STR28## wherein X independently represents alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, alkylsulfonyl of 1 to 4 carbon atoms, trifluoromethyl, 3,4-methylenedioxy, chloro, fluoro or bromo; n represents an integer of 0 to 2; Y represents oxygen or sulfur; R represents hydrogen, cyano or ethynyl and Z represents chloro, fluoro or bromo.
Claim 3
Dependent Claim
11 words
A compound as defined in claim 1 wherein Y is oxygen.
Claim 4
Dependent Claim
11 words
A compound as defined in claim 1 wherein Z is chloro.
Claim 5
Dependent Claim
11 words
A compound as defined in claim 1 wherein R is cyano.
Claim 6
Dependent Claim
11 words
A compound as defined in claim 2 wherein R is cyano.
Claim 7
Dependent Claim
11 words
A compound as defined in claim 5 wherein Z is chloro.
Claim 8
Dependent Claim
11 words
A compound as defined in claim 6 wherein n is 0.
Claim 9
Dependent Claim
13 words
The compound as defined in claim 7 which is 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane carboxylic acid:cyano(6-phenoxy-2-pyridinyl)methyl ester.
Claim 10
Dependent Claim
13 words
The compound as defined in claim 7 which is cis-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane carboxylic acid:cyano(6-phenoxy-2-pyridinyl)methyl ester.
Claim 11
Dependent Claim
13 words
The compound as defined in claim 7 which is trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane carboxylic acid:cyano(6-phenoxy-2-pyridinyl)methyl ester.
Claim 12
Dependent Claim
11 words
A compound as defined in claim 6 wherein n is 1.
Claim 13
Dependent Claim
13 words
The compound as defined in claim 11 which is 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane carboxylic acid:cyano(6-(4-methoxyphenoxy)-2-pyridinyl)-methyl ester.
Claim 14
Dependent Claim
13 words
The compound as defined in claim 11 which is 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane carboxylic acid:cyano(6-(4-chlorophenoxy)-2-pyridinyl)methyl ester.
Claim 15
Dependent Claim
13 words
The compound as defined in claim 11 which is 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane carboxylic acid:cyano(6-(3-fluorophenoxy)-2-pyridinyl)methyl ester.
Claim 16
Dependent Claim
13 words
The compound as defined in claim 11 which is 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane carboxylic acid:cyano(6-(4-fluorophenoxy)-2-pyridinyl)methyl ester.
Claim 17
Dependent Claim
92 words
An insecticidal composition comprising as the active ingredient, an insecticidally effective amount of a compound corresponding to the formula ##STR29## wherein X independently represents alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, alkylsulfonyl of 1 to 4 carbon atoms, trifluoromethyl, 3,4-methylenedioxy, chloro, fluoro or bromo; n represents an integer of 0 to 2; Y represents oxygen or sulfur; R represents hydrogen, cyano or ethynyl and Z represents chloro, fluoro or bromo, in intimate admixture with an inert carrier therefor.
Claim 18
Dependent Claim
92 words
An insecticidal composition comprising as the active ingredient, an insecticidally effective amount of a compound corresponding to the formula ##STR29## wherein X independently represents alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, alkylsulfonyl of 1 to 4 carbon atoms, trifluoromethyl, 3,4-methylenedioxy, chloro, fluoro or bromo; n represents an integer of 0 to 2; Y represents oxygen or sulfur; R represents hydrogen, cyano or ethynyl and Z represents chloro, fluoro or bromo, in intimate admixture with an inert carrier therefor.
Claim 19
Dependent Claim
11 words
A composition as defined in claim 16 wherein Y is oxygen.
Claim 20
Dependent Claim
11 words
A composition as defined in claim 16 wherein Z is chloro.
Claim 21
Dependent Claim
11 words
A composition as defined in claim 16 wherein R is cyano.
Claim 22
Dependent Claim
11 words
A composition as defined in claim 17 wherein R is cyano.
Claim 23
Dependent Claim
11 words
A composition as defined in claim 20 wherein Z is chloro.
Claim 24
Dependent Claim
11 words
A composition as defined in claim 21 wherein n is 0.
Claim 25
Dependent Claim
15 words
The composition as defined in claim 22 wherein the compound is 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane carboxylic acid:cyano(6-phenoxy-2-pyridinyl)methyl ester.
Claim 26
Dependent Claim
15 words
The composition as defined in claim 22 wherein the compound is cis-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane carboxlic acid:cyano(6-phenoxy-2-pyridinyl)methyl ester.
Claim 27
Dependent Claim
15 words
The composition as defined in claim 22 wherein the compound is trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane carboxylic acid:cyano(6-phenoxy-2-pyridinyl)methyl ester.
Claim 28
Dependent Claim
11 words
A composition as defined in claim 21 wherein n is 1.
Claim 29
Dependent Claim
15 words
The composition as defined in claim 26 wherein the compound is 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane carboxylic acid:cyano(6-(4-methoxyphenoxy)-2-pyridinyl)methyl ester.
Claim 30
Dependent Claim
15 words
The composition as defined in claim 26 wherein the compound is 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane carboxylic acid:cyano(6-(4-chlorophenoxy)-2-pyridinyl)methyl ester.
Claim 31
Dependent Claim
15 words
The composition as defined in claim 26 wherein the compound is 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane carboxylic acid:cyano(6-(3-fluorophenoxy)-2-pyridinyl)methyl ester.
Claim 32
Dependent Claim
15 words
The composition as defined in claim 26 wherein the compound is 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane carboxylic acid:cyano(6-(4-fluorophenoxy)-2-pyridinyl)methyl ester.
Claim 33
Independent Claim
109 words
A method for the kill and control of insects which comprises contacting said insects or their habitat with a composition containing as the active ingredient, an insecticidally effective amount of a compound corresponding to the formula ##STR30## wherein X independently represents alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, alkylsulfonyl of 1 to 4 carbon atoms, trifluoromethyl, 3,4-methylenedioxy, chloro, fluoro or bromo; n represents an integer of 0 to 2; Y represents oxygen or sulfur; R represents hydrogen, cyano or ethynyl and Z represents chloro, fluoro or bromo, in intimate admixture with an inert carrier therefor.
Claim 34
Independent Claim
109 words
A method for the kill and control of insects which comprises contacting said insects or their habitat with a composition containing as the active ingredient, an insecticidally effective amount of a compound corresponding to the formula ##STR30## wherein X independently represents alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, alkylsulfonyl of 1 to 4 carbon atoms, trifluoromethyl, 3,4-methylenedioxy, chloro, fluoro or bromo; n represents an integer of 0 to 2; Y represents oxygen or sulfur; R represents hydrogen, cyano or ethynyl and Z represents chloro, fluoro or bromo, in intimate admixture with an inert carrier therefor.
Claim 35
Dependent Claim
11 words
A method as defined in claim 31 wherein Y is oxygen.
Claim 36
Dependent Claim
11 words
A method as defined in claim 31 wherein Z is chloro.
Claim 37
Dependent Claim
11 words
A method as defined in claim 31 wherein R is cyano.
Claim 38
Dependent Claim
11 words
A method as defined in claim 32 wherein R is cyano.
Claim 39
Dependent Claim
11 words
A method as defined in claim 35 wherein Z is chloro.
Claim 40
Dependent Claim
11 words
A method as defined in claim 36 wherein n is 0.
Claim 41
Dependent Claim
16 words
The method as defined in claim 37 wherein the active ingredient is 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane carboxylic acid:cyano(6-phenoxy-2-pyridinyl)methyl ester.
Claim 42
Dependent Claim
16 words
The method as defined in claim 37 wherein the active ingredient is cis-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane carboxylic acid:cyano(6-phenoxy-2-pyridinyl)methyl ester.
Claim 43
Dependent Claim
16 words
The method as defined in claim 37 wherein the active ingredient is trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane carboxylic acid:cyano(6-phenoxy-2-pyridinyl)methyl ester.
Claim 44
Dependent Claim
11 words
A method as defined in claim 36 wherein n is 1.
Claim 45
Dependent Claim
16 words
The method as defined in claim 41 wherein the active ingredient is 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane carboxylic acid:cyano(6-(4-methoxyphenoxy)-2-pyridinyl)methyl ester.
Claim 46
Dependent Claim
16 words
The method as defined in claim 41 wherein the active ingredient is 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane carboxylic acid:cyano(6-(4-chlorophenoxy)-2-pyridinyl)methyl ester.
Claim 47
Dependent Claim
16 words
The method as defined in claim 41 wherein the active ingredient is 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane carboxylic acid:cyano(6-(3-fluorophenoxy)-2-pyridinyl)methyl ester.
Claim 48
Dependent Claim
16 words
The method as defined in claim 41 wherein the active ingredient is 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane carboxylic acid:cyano(6-(4-fluorophenoxy)-2-pyridinyl)methyl ester.
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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) | 1982-08-06 | 1983-02-05 | 1983-08-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-08-06 | 1987-02-05 | 1987-08-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-08-06 | 1991-02-05 | 1991-08-07 | $7700.00 | Window Closed / Lapsed |