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US4262014A
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Insecticidal esters
Assignee: Commonwealth Scientific and Industrial Research Organisation
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Filing: 1978-08-10
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Granted: 1981-04-14
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Expires: 1998-08-10
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 groups (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 07:35
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: 17
Claim 1
Independent Claim
59 words
The (+), (-) and (±) forms of the compounds of the general formula I ##STR10## wherein R 1 and R 2 together form a methylenedioxy group; R 3 is one of the following groups (a) to (d): ##STR11## and R 4 and R 5 are the same or different groups and each is a fluoro, bromo or chloro group.
Claim 2
Dependent Claim
59 words
The (+), (-) and (±) forms of the compounds of the general formula I ##STR10## wherein R 1 and R 2 together form a methylenedioxy group; R 3 is one of the following groups (a) to (d): ##STR11## and R 4 and R 5 are the same or different groups and each is a fluoro, bromo or chloro group.
Claim 3
Dependent Claim
13 words
The (+), (-) and (±) forms of the 2-benzyl-4-furylmethyl esters of 1-(3,4-methylenedioxyphenyl)-2,2-dichlorocyclopropane-1-carboxylic acid.
Claim 4
Dependent Claim
13 words
The (+), (-) and (±) forms of the 2-benzyl-4-furylmethyl esters of 1-(3,4-methylenedioxyphenyl)-2,2-dichlorocyclopropane-1-carboxylic acid.
Claim 5
Dependent Claim
13 words
The (+), (-) and (±) forms of the m-phenoxy-α-cyanobenzyl esters of 1-(3,4-methylenedioxyphenyl)-2,2-dichlorocyclopropane-1-carboxylic acid.
Claim 6
Dependent Claim
13 words
The (+), (-) and (±) forms of the m-phenoxy-α-cyanobenzyl esters of 1-(3,4-methylenedioxyphenyl)-2,2-dichlorocyclopropane-1-carboxylic acid.
Claim 7
Dependent Claim
13 words
The 3,4-methylenedioxybenzyl ester of 1-(3,4-methylenedioxyphenyl)-2,2-dichlorocyclopropane-1-carboxylic acid, in its (+), (-) and (±) forms.
Claim 8
Dependent Claim
13 words
The 3,4-methylenedioxybenzyl ester of 1-(3,4-methylenedioxyphenyl)-2,2-dichlorocyclopropane-1-carboxylic acid, in its (+), (-) and (±) forms.
Claim 9
Dependent Claim
74 words
The (+), (-) and (±) forms of the compounds having the general formula I ##STR12## wherein R 1 is hydrogen or a methoxy, ethoxy, propoxy, methylthio, ethylthio, propylthio, fluoro, chloro, bromo, methyl, ethyl, nitro or amino group, and R 2 is a hydrogen or methyl group and R 3 is the group ##STR13## and R 4 and R 5 are the same or different groups and each is a fluoro, bromo or chloro group.
Claim 10
Dependent Claim
74 words
The (+), (-) and (±) forms of the compounds having the general formula I ##STR12## wherein R 1 is hydrogen or a methoxy, ethoxy, propoxy, methylthio, ethylthio, propylthio, fluoro, chloro, bromo, methyl, ethyl, nitro or amino group, and R 2 is a hydrogen or methyl group and R 3 is the group ##STR13## and R 4 and R 5 are the same or different groups and each is a fluoro, bromo or chloro group.
Claim 11
Dependent Claim
48 words
Insecticidal compositions comprising an insecticidally effective amount of at least one compound of formula I as set forth in claim 1, incorporated in a suitable inert solvent, or mixture of solvents, or in a solid mixture, with or without other substances, such as wetting, dispersing and sticking agents.
Claim 12
Dependent Claim
23 words
Insecticidal compositions as claimed in claim 6, additionally containing at least one synergistic or potentiating agent of the class of microsomal oxidase inhibitors.
Claim 13
Dependent Claim
16 words
Insecticidal compositions as claimed in claim 7, wherein the synergist or potentiator is a pyrethrin synergist.
Claim 14
Dependent Claim
22 words
Insecticidal compositions as claimed in claim 7, wherein the synergist is one of the following 60 -[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)-4-[2-(octylsulfinyl)propyl]-benzene, or dipropyl-5,6,7,8-tetrahydro-7-methylnaphtho-[2,3-d]-1,3-dioxole-5,6-dicarboxylate.
Claim 15
Dependent Claim
30 words
Insecticidal compositions as claimed in claim 7, wherein the synergist is 2-(3,4-methylenedioxyphenoxy)-3,6,9-trioxaundecane or piperonyl butoxide used in an amount from 1/1000th to 5 times the weight of the compound I.
Claim 16
Dependent Claim
32 words
Insecticidal compositions as claimed in claim 10, wherein the amount of 2-(3,4-methylenedioxyphenoxy)-3,6,9-trioxaundecane or piperonyl butoxide used is from about 1/100th to an equal part by weight per part of the compound I.
Claim 17
Dependent Claim
49 words
Insecticidal compositions comprising an insecticidally effective amount of one or more of the compounds of formula I, as stated in claim 5 incorporated in a suitable inert solvent, or mixture of solvents, or in a solid mixture, with or without other substances, such as wetting, dispersing and sticking agents.
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) | 1984-04-13 | 1984-10-13 | 1985-04-14 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-04-13 | 1988-10-13 | 1989-04-14 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-04-13 | 1992-10-13 | 1993-04-14 | $7700.00 | Window Closed / Lapsed |