US4221799A
Expired / Lapsed
US
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Substituted pyridine methyl esters of tetramethyl cyclopropane carboxylic acids and their use as insecticides
Assignee: Dow Chemical Co
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Filing: 1979-07-30
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Granted: 1980-09-09
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Expires: 1999-07-30
Abstract
Abstract Substituted pyridine methyl esters of tetramethylcyclopropane carboxylic acids and the optical isomers thereof are prepared which correspond to the formula: ##STR1## wherein n represents an integer of 0 to 2; X independently represents alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, alkylsulfinyl of 1 to 4 carbon atoms, alkylsulfonyl of 1 to 4 carbon atoms, trifluoromethyl, nitro, cyano, chloro, fluoro, bromo, or 3,4-methylenedioxy (when n is 2 and both X's are taken together); and R represents hydrogen, cyano or ethynyl. These compounds have been found to exhibit a high degree of insecticidal activity and compositions containing said compounds are so employed.
Inventors
- 👤 John C. Van Heertum
- 👤 Sudarshan K. Malhotra
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 03:34
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
Claims Analysis
Total Claims: 36
Claim 1
Independent Claim
73 words
A compound corresponding to the formula ##STR29## wherein n represents an integer of 0 to 2; X independently represents alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, alkylsulfinyl of 1 to 4 carbon atoms, alkylsulfonyl of 1 to 4 carbon atoms, trifluoromethyl, chloro, fluoro, bromo; n represents an integer of 0 to 2; and R represent hydrogen, cyano or ethynyl.
Claim 2
Dependent Claim
73 words
A compound corresponding to the formula ##STR29## wherein n represents an integer of 0 to 2; X independently represents alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, alkylsulfinyl of 1 to 4 carbon atoms, alkylsulfonyl of 1 to 4 carbon atoms, trifluoromethyl, chloro, fluoro, bromo; n represents an integer of 0 to 2; and R represent hydrogen, cyano or ethynyl.
Claim 3
Dependent Claim
11 words
A compound as defined in claim 1 wherein R is hydrogen.
Claim 4
Dependent Claim
11 words
A compound as defined in claim 1 wherein R is ethynyl.
Claim 5
Dependent Claim
11 words
A compound as defined in claim 1 wherein R is cyano.
Claim 6
Dependent Claim
13 words
The compound as defined in claim 2 which is 2,2,3,3-tetramethylcyclopropane carboxylic acid:(6-phenoxy-2-pyridinyl)methyl ester.
Claim 7
Dependent Claim
13 words
The compound as defined in claim 3 which is 2,2,3,3-tetramethylcyclopropane carboxylic acid:1-(6-phenoxy-2-pyridinyl)-2-propynyl ester.
Claim 8
Dependent Claim
13 words
The compound as defined in claim 4 which is 2,2,3,3-tetramethylcyclopropane carboxylic acid:cyano(6-phenoxy-2-pyridinyl)methyl ester.
Claim 9
Dependent Claim
13 words
The compound as defined in claim 4 which is 2,2,3,3-tetramethylcyclopropane caboxylic acid:cyano(6-(4-methoxyphenoxy)-2-pyridinyl)methyl ester.
Claim 10
Dependent Claim
13 words
The compound as defined in claim 4 which is 2,2,3,3-tetramethylcyclopropane carboxylic acid:cyano(6-(4-chlorophenoxy)-2-pyridinyl)methyl ester.
Claim 11
Dependent Claim
13 words
The compound as defined in claim 4 which is 2,2,3,3-tetramethylcyclopropane carboxylic acid:cyano(6-(3-fluorophenoxy)-2-pyridinyl)methyl ester.
Claim 12
Dependent Claim
13 words
The compound as defined in claim 4 which is 2,2,3,3-tetramethylcyclopropane carboxylic acid:cyano(6-(4-fluorophenoxy)-2-pyridinyl)methyl ester.
Claim 13
Dependent Claim
90 words
An insecticidal composition comprising an inert carrier and as the active ingredient, an insecticidally effective amount of a compound corresponding to the formula ##STR30## wherein n represents an integer of 0 to 2; X independently represents alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, alkylsulfinyl of 1 to 4 carbon atoms, alkylsulfonyl of 1 to 4 carbon atoms, trifluoromethyl, chloro, fluoro, bromo; n represents an integer of 0 to 2; and R represents hydrogen, cyano or ethynyl.
Claim 14
Dependent Claim
90 words
An insecticidal composition comprising an inert carrier and as the active ingredient, an insecticidally effective amount of a compound corresponding to the formula ##STR30## wherein n represents an integer of 0 to 2; X independently represents alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, alkylsulfinyl of 1 to 4 carbon atoms, alkylsulfonyl of 1 to 4 carbon atoms, trifluoromethyl, chloro, fluoro, bromo; n represents an integer of 0 to 2; and R represents hydrogen, cyano or ethynyl.
Claim 15
Dependent Claim
11 words
A composition as defined in claim 12 wherein R is hydrogen.
Claim 16
Dependent Claim
11 words
A composition as defined in claim 12 wherein R is ethynyl.
Claim 17
Dependent Claim
11 words
A composition as defined in claim 12 wherein R is cyano.
Claim 18
Dependent Claim
15 words
The composition as defined in claim 13 wherein the compound is 2,2,3,3-tetramethylcyclopropane carboxylic acid:(6-phenoxy-2-pyridinyl)-methyl ester.
Claim 19
Dependent Claim
15 words
The compound as defined in claim 14 wherein the compound is 2,2,3,3-tetramethylcyclopropane caboxylic acid:(6-phenoxy-2-pyridinyl)-2-propynyl ester.
Claim 20
Dependent Claim
15 words
The composition as defined in claim 15 wherein the compound is 2,2,3,3-tetramethylcyclopropane carboxylic acid:cyano(6-phenoxy-2-pyridinyl)-methyl ester.
Claim 21
Dependent Claim
16 words
The composition as defined as in claim 15 wherein the compound is 2,2,3,3-tetramethylcyclopropane carboxylic acid:cyano(6-(4-methoxyphenoxy)-2-pyridinyl)methyl ester.
Claim 22
Dependent Claim
15 words
The composition as defined in claim 15 wherein the compound is 2,2,3,3-tetramethylcyclopropane carboxylic acid:cyano(6-(4-chlorophenoxy)-2-pyridinyl)methyl ester.
Claim 23
Dependent Claim
15 words
The composition as defined in claim 15 wherein the compound is 2,2,3,3-tetramethylcyclopropane carboxylic acid:cyano(6-(3-fluorophenoxy)-2-pyridinyl)methyl ester.
Claim 24
Dependent Claim
15 words
The composition as defined in claim 15 wherein the compound is 2,2,3,3-tetramethylcyclopropane carboxylic acid:cyano(6-(4-fluorophenoxy)-2-pyridinyl)methyl ester.
Claim 25
Independent Claim
107 words
A method for the kill and control of insects which comprises contacting said insects or their habitat with a composition containing an inert carrier and as the active ingredient, an insecticidally effective amount of a compound corresponding to the formula ##STR31## wherein n represents an integer of 0 to 2; X independently represents alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, alkylsulfinyl of 1 to 4 carbon atoms, alkylsulfonyl of 1 to 4 carbon atoms, trifluoromethyl, chloro, fluoro, bromo; n represents an integer of 0 to 2; and R represents hydrogen, cyano or ethynyl.
Claim 26
Independent Claim
107 words
A method for the kill and control of insects which comprises contacting said insects or their habitat with a composition containing an inert carrier and as the active ingredient, an insecticidally effective amount of a compound corresponding to the formula ##STR31## wherein n represents an integer of 0 to 2; X independently represents alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, alkylsulfinyl of 1 to 4 carbon atoms, alkylsulfonyl of 1 to 4 carbon atoms, trifluoromethyl, chloro, fluoro, bromo; n represents an integer of 0 to 2; and R represents hydrogen, cyano or ethynyl.
Claim 27
Dependent Claim
11 words
A method as defined in claim 23 wherein R is hydrogen.
Claim 28
Dependent Claim
11 words
A method as defined in claim 23 wherein R is ethynyl.
Claim 29
Dependent Claim
11 words
A method as defined in claim 23 wherein R is cyano.
Claim 30
Dependent Claim
16 words
The method as defined in claim 24 wherein the active ingredient is 2,2,3,3-tetramethylcyclopropane carboxylic acid:(6-phenoxy-2-pyridinyl)methyl ester.
Claim 31
Dependent Claim
16 words
The method as defined in claim 25 wherein the active ingredient is 2,2,3,3-tetramethylcyclopropane carboxylic acid:cyano(6-phenoxy-2-pyridinyl)-2-propynyl ester.
Claim 32
Dependent Claim
16 words
The method as defined in claim 26 wherein the active ingredient is 2,2,3,3-tetramethylcyclopropane carboxylic acid:cyano(6-phenoxy-2-pyridinyl)methyl ester.
Claim 33
Dependent Claim
16 words
The method as defined in claim 26 wherein the active ingredient is 2,2,3,3-tetramethylcyclopropane carboxylic acid:cyano(6-(4-methoxyphenoxy)-2-pyridinyl)methyl ester.
Claim 34
Dependent Claim
16 words
The method as defined in claim 26 wherein the active ingredient is 2,2,3,3-tetramethylcyclopropane carboxylic acid:cyano(6-(4-chlorophenoxy)-2-pyridinyl)methyl ester.
Claim 35
Dependent Claim
16 words
The method as defined in claim 26 wherein the active ingredient is 2,2,3,3-tetramethylcyclopropane carboxylic acid:cyano(6-(3-fluorophenoxy)-2-pyridinyl)methyl ester.
Claim 36
Dependent Claim
16 words
The method as defined in claim 26 wherein the active ingredient is 2,2,3,3-tetramethylcyclopropane carboxylic acid:cyano(6-(4-fluorophenoxy)-2-pyridinyl)methyl ester.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-09-09 | 1984-03-10 | 1984-09-09 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-09-09 | 1988-03-10 | 1988-09-09 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-09-09 | 1992-03-10 | 1992-09-09 | $7700.00 | Window Closed / Lapsed |