Patent US4220591A successfully refreshed from Google Patents.
US4220591A
Expired / Lapsed
US
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Insecticidal esters
Assignee: Commonwealth Scientific and Industrial Research Organisation
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Filing: 1976-11-17
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Granted: 1980-09-02
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Expires: 1996-11-17
Abstract
Abstract The (+), (-) and (+/-) forms of the compounds of formula I <IMAGE> wherein R1 is hydrogen or a methoxy, ethoxy, propoxy, methylthio, ethylthio, propylthio, fluoro, chloro, bromo, methyl, ethyl, nitro or amino group, and R2 is a hydrogen or methyl group or R1 and R2 together form a methylenedioxy group; R3 is hydrogen, or a lower alkyl group, or one of the following groups (a) to (d): (a) m-phenoxybenzyl (b) 2-benzyl-4-furylmethyl (c) alpha -cyano-m-phenoxybenzyl (d) 3,4-methylenedioxy-benzyl, and R4 and R5 are the same or different groups and each is a fluoro, bromo, chloro or methyl group. The compounds of formula I in which R3 is one of group (a) to (d) are extremely active as insecticides (except when R1 is an amino group). The compounds also possess the property of contact repellency to insects.
Inventors
- 👤 George Holan
- 👤 Reimund A. Walser
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 12:55
CPC Classifications
C; C07; C07D; C07D307/00; C07D307/02; C07D307/34; C07D307/38; C07D307/40; C07D307/42; A; A01; A01N; A01N53/00; C07C; C07C255/00; C07D307/54; C07D317/00; C07D317/08; C07D317/44; C07D317/46; C07D317/48; C07D317/50; C07D317/60
Claims Analysis
Total Claims: 31
Claim 1
Independent Claim
95 words
The (+), (-), and (±) forms of the compounds of the general formula I ##STR12## wherein R' is hydrogen or a methoxy, ethoxy, propoxy, methylthio, ethylthio, propylthio, fluoro, chloro, bromo, methyl, ethyl, nitro or amino group, and R 2 is hydrogen or methyl or R 1 and R 2 together form a methylenedioxy group, provided, however, that R 1 and R 2 are not both hydrogen; R 3 is hydrogen or lower alkyl; and R 4 and R 5 are the same or different groups and each is a fluoro, bromo, chloro or methyl group.
Claim 2
Dependent Claim
95 words
The (+), (-), and (±) forms of the compounds of the general formula I ##STR12## wherein R' is hydrogen or a methoxy, ethoxy, propoxy, methylthio, ethylthio, propylthio, fluoro, chloro, bromo, methyl, ethyl, nitro or amino group, and R 2 is hydrogen or methyl or R 1 and R 2 together form a methylenedioxy group, provided, however, that R 1 and R 2 are not both hydrogen; R 3 is hydrogen or lower alkyl; and R 4 and R 5 are the same or different groups and each is a fluoro, bromo, chloro or methyl group.
Claim 3
Dependent Claim
11 words
The (-) epimer of the m-phenoxybenzyl ester of 1-p-ethoxyphenyl-2,2-dichlorocyclopropane-1 carboxylic acid.
Claim 4
Dependent Claim
11 words
The (-) epimer of the m-phenoxybenzyl ester of 1-p-ethoxyphenyl-2,2-dichlorocyclopropane-1 carboxylic acid.
Claim 5
Dependent Claim
13 words
1-p-Chlorophenyl-2,2-dichlorocyclopropane-1-carboxylic acid and its ethyl ester, in their (+), (-) and (±) forms.
Claim 6
Dependent Claim
13 words
1-p-Chlorophenyl-2,2-dichlorocyclopropane-1-carboxylic acid and its ethyl ester, in their (+), (-) and (±) forms.
Claim 7
Dependent Claim
13 words
1-p-Ethoxyphenyl-2,2-dichlorocyclopropane-1-carboxylic acid and its ethyl ester, in their (+), (-) and (±) forms.
Claim 8
Dependent Claim
13 words
1-p-Ethoxyphenyl-2,2-dichlorocyclopropane-1-carboxylic acid and its ethyl ester, in their (+), (-) and (±) forms.
Claim 9
Dependent Claim
13 words
1-(3,4-Methylenedioxyphenyl)-2,2-dichlorocyclopropane-1-carboxylic acid and its ethyl ester, in their (+), (-) and (±) forms.
Claim 10
Dependent Claim
13 words
1-(3,4-Methylenedioxyphenyl)-2,2-dichlorocyclopropane-1-carboxylic acid and its ethyl ester, in their (+), (-) and (±) forms.
Claim 11
Dependent Claim
13 words
1-p-Ethoxyphenyl-2,2-dibromocyclopropane-1-carboxylic acid and its ethyl ester, in their (+), (-) and (±) forms.
Claim 12
Dependent Claim
13 words
1-p-Ethoxyphenyl-2,2-dibromocyclopropane-1-carboxylic acid and its ethyl ester, in their (+), (-) and (±) forms.
Claim 13
Dependent Claim
13 words
1-p-Ethoxyphenyl-2,2-difluorocyclopropane-1-carboxylic acid and its ethyl ester, in their (+), (-) and (±) forms.
Claim 14
Dependent Claim
13 words
1-p-Ethoxyphenyl-2,2-difluorocyclopropane-1-carboxylic acid and its ethyl ester, in their (+), (-) and (±) forms.
Claim 15
Dependent Claim
13 words
The (+), (-) and (±) forms of the m-phenoxy-α-cyanobenzyl ester of: 1-p-ethoxyphenyl-2,2-dichlorocyclopropane-1-carboxylic acid.
Claim 16
Dependent Claim
13 words
The (+), (-) and (±) forms of the m-phenoxy-α-cyanobenzyl ester of: 1-p-ethoxyphenyl-2,2-dichlorocyclopropane-1-carboxylic acid.
Claim 17
Dependent Claim
67 words
The (+), (-) and (±) forms of the compounds of the formula I ##STR13## wherein R 1 is hydrogen or a methoxy, ethoxy, propoxy, methylthio, ethylthio, propylthio, fluoro, chloro, bromo, methyl, ethyl or nitro, and R 2 is hydrogen or methyl; R 3 is ##STR14## and R 4 and R 5 are the same or different groups and each is a fluoro, bromo, chloro or methyl group.
Claim 18
Dependent Claim
67 words
The (+), (-) and (±) forms of the compounds of the formula I ##STR13## wherein R 1 is hydrogen or a methoxy, ethoxy, propoxy, methylthio, ethylthio, propylthio, fluoro, chloro, bromo, methyl, ethyl or nitro, and R 2 is hydrogen or methyl; R 3 is ##STR14## and R 4 and R 5 are the same or different groups and each is a fluoro, bromo, chloro or methyl group.
Claim 19
Dependent Claim
22 words
The (+), (-) and (±) forms of the m-phenoxybenzyl esters of 1-p-chlorophenyl-1,2,-dichlorocyclopropane-1-carboxylic acid, 1-p-ethoxyphenyl-2,2-dichlorocyclopropane-1-carboxylic acid, 1-p-ethoxyphenyl-2,2-dibromocyclopropane-1-carboxylic acid, 1-p-ethoxyphenyl-2,2-difluorocyclopropane-1-carboxylic acid, or 1-p-ethoxyphenyl-2,2-dimethylcyclopropane-1-carboxylic acid.
Claim 20
Dependent Claim
22 words
The (+), (-) and (±) forms of the m-phenoxybenzyl esters of 1-p-chlorophenyl-1,2,-dichlorocyclopropane-1-carboxylic acid, 1-p-ethoxyphenyl-2,2-dichlorocyclopropane-1-carboxylic acid, 1-p-ethoxyphenyl-2,2-dibromocyclopropane-1-carboxylic acid, 1-p-ethoxyphenyl-2,2-difluorocyclopropane-1-carboxylic acid, or 1-p-ethoxyphenyl-2,2-dimethylcyclopropane-1-carboxylic acid.
Claim 21
Dependent Claim
27 words
The (+), (-) and (±) forms of m-phenoxybenzyl esters of 1-p-methoxyphenyl-2-chloro-2-fluorocyclopropane-1-carboxylic acid, 1-p-ethoxyphenyl-2-bromo-2-chloro-2-fluorocyclopropane-1-carboxylic acid, 1-p-ethylthiophenyl-2,2-dichlorocyclopropane-1-carboxylic acid, 1-m-tolyl-2,2-dichlorocyclopropane-1-carboxylic acid, 1-p-ethylphenyl-2,2-dichlorocyclopropane-1-carboxylic acid, 1-p-nitrophenyl-2,2-dichlorocyclopropane-1-carboxylic acid, 1-phenyl-2,2-dichlorocyclopropane-1-carboxylic acid, or 1-p-bromophenyl-2,2-dichlorocyclopropane-1-carboxylic acid.
Claim 22
Dependent Claim
27 words
The (+), (-) and (±) forms of m-phenoxybenzyl esters of 1-p-methoxyphenyl-2-chloro-2-fluorocyclopropane-1-carboxylic acid, 1-p-ethoxyphenyl-2-bromo-2-chloro-2-fluorocyclopropane-1-carboxylic acid, 1-p-ethylthiophenyl-2,2-dichlorocyclopropane-1-carboxylic acid, 1-m-tolyl-2,2-dichlorocyclopropane-1-carboxylic acid, 1-p-ethylphenyl-2,2-dichlorocyclopropane-1-carboxylic acid, 1-p-nitrophenyl-2,2-dichlorocyclopropane-1-carboxylic acid, 1-phenyl-2,2-dichlorocyclopropane-1-carboxylic acid, or 1-p-bromophenyl-2,2-dichlorocyclopropane-1-carboxylic acid.
Claim 23
Dependent Claim
19 words
Insecticidal compositions comprising at least one of the compounds of formula I of claim 9, incorporated with a carrier.
Claim 24
Dependent Claim
23 words
Insecticidal compositions as claimed in claim 12, additionally containing at least one synergistic or potentiating agent of the class of microsomal oxidase inhibitors.
Claim 25
Dependent Claim
21 words
Insecticidal compositions as claimed in claim 13 wherein the synergist is one of the following α-[2-(2-butoxyethoxy)ethoxy]-4,5-methylenedioxy-2-propyltoluene, 3-hexyl-5(3,4-methylenedioxyphenyl)-2-cyclohexanone, 2-(3,4-methylenedioxy-phenoxy)-3,6,9-trioxaundecane, 1,2-(methylenedioxy-phenoxy)-4-[2-(octyl-sulfinyl)propyl]-benzene, or dipropyl-5,6,7,8-tetrahydro-7-methylnaphtho-[2,3-d]-1,3-dioxole-5,6-dicarboxylate.
Claim 26
Dependent Claim
16 words
Insecticidal compositions as claimed in claim 13, wherein the synergist or potentiator is a pyrethrin synergist.
Claim 27
Dependent Claim
29 words
Insecticidal compositions as claimed in claim 13, wherein the synergist is α-[2-(2-buthoxyethoxy)ethoxy]-4,5-methylenedioxy-2-propyltoluene, or 2-(3,4-methylenedioxy-phenoxy)-3,6,9-trioxaundecane used in an amount from 1/1000th to 5 times the weight of the compound I.
Claim 28
Dependent Claim
31 words
Insecticidal compositions as claimed in claim 13, wherein the amount of 2-(3,4-methylenedioxy-phenoxy)-3,6,9-trioxaundecane, or α-[2-(2-butoxyethoxy)ethoxy]-4,5-methylenedioxy-2-propyltoluene used is from about 1/100th to an equal part by weight per part of the compound I.
Claim 29
Dependent Claim
22 words
The compounds of claim 1 wherein R 1 is hydrogen, methoxy, ethoxy, propoxy, methylthio, ethylthio, propylthio, fluoro, chloro, bromo, methyl, or ethyl.
Claim 30
Dependent Claim
24 words
The compounds of claim 9 wherein R 1 is hydrogen or a methoxy, ethoxy, propoxy, methylthio, ethylthio, propylthio, fluoro, chloro, bromo, methyl, or ethyl.
Claim 31
Dependent Claim
29 words
The compound of claim 1 wherein R 1 is hydrogen, methoxy, ethoxy, propoxy, methylthio, ethylthio, propylthio, fluoro, chloro, bromo, methyl or ethyl and R 2 is hydrogen or methyl.
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) | 1983-09-02 | 1984-03-03 | 1984-09-02 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-09-02 | 1988-03-03 | 1988-09-02 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-09-02 | 1992-03-03 | 1992-09-02 | $7700.00 | Window Closed / Lapsed |