Patent US4277490A successfully refreshed from Google Patents.
US4277490A
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Insecticidal 1-(2-naphthyl)-cyclobutane carboxylate
Assignee: Commonwealth Scientific and Industrial Research Organisation
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Filing: 1979-11-30
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Granted: 1981-07-07
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Expires: 1999-11-30
Abstract
Abstract New compounds are described that fall within the general formula I <IMAGE> wherein R is hydrogen, or a lower alkyl group, or one of the following groups: (a) 3-phenoxybenzyl (b) 2-benzyl-4-furylmethyl (c) alpha -cyano-3-phenoxybenzyl (d) 3,4-methylenedioxybenzyl (e) alpha -ethynyl-3-phenoxybenzyl (f) alpha -cyano-3-(4-chlorophenoxy)-benzyl and A is one of the groups X or Y <IMAGE> wherein X1, X2, X3 and X4 are the same or different groups and each is hydrogen or fluoro, chloro, bromo or methyl group, with the proviso that if X1 or X3 is a fluoro group then X2 or X4 should not be a bromo group; and wherein Y1, Y2, Y3, Y4, Y5 and Y6 are the same or different groups and each is hydrogen or a fluoro, bromo, chloro or methyl group. Processes of making the compounds are described. The compounds in which R3 is one of groups (a) to (f) are insecticides and insecticidal methods and compositions containing them are described.
Inventors
- 👤 George Holan
- 👤 Reimund A. Walser
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 07:45
CPC Classifications
C; C07; C07C; C07C255/00; A; A01; A01N; A01N37/00; A01N37/10; A01N37/36; A01N37/38; A01N53/00
Claims Analysis
Total Claims: 25
Claim 1
Independent Claim
71 words
The (+), (-), and (±) forms of the compounds of the general formula I ##STR16## wherein R is one of the following groups (a) to (f): ##STR17## and A is the group Y ##STR18## wherein Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , and Y 6 are the same or different groups and each is hydrogen or a fluoro, bromo, chloro, or methyl group.
Claim 2
Dependent Claim
71 words
The (+), (-), and (±) forms of the compounds of the general formula I ##STR16## wherein R is one of the following groups (a) to (f): ##STR17## and A is the group Y ##STR18## wherein Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , and Y 6 are the same or different groups and each is hydrogen or a fluoro, bromo, chloro, or methyl group.
Claim 3
Dependent Claim
9 words
The compound of claim 1 wherein R is (a).
Claim 4
Dependent Claim
9 words
The compound of claim 1 wherein R is (b).
Claim 5
Dependent Claim
9 words
The compound of claim 1 wherein R is (c).
Claim 6
Dependent Claim
9 words
The compound of claim 1 wherein R is (d).
Claim 7
Dependent Claim
9 words
The compound of claim 1 wherein R is (e).
Claim 8
Dependent Claim
9 words
The compound of claim 1 wherein R is (f).
Claim 9
Dependent Claim
39 words
The compound of claim 1 wherein Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , and Y 6 are the same or different groups and each is a fluoro, bromo, or chloro group.
Claim 10
Dependent Claim
24 words
Compounds as claimed in claim 1, characterised in that R is one of the groups (a), (c) and (e) as defined in claim 1.
Claim 11
Dependent Claim
35 words
Compounds as claimed in claim 1, characterised in that at least two of the groups Y 1 through Y 4 are F and the remainder, if any, are H and Y 5 =Y 6 =H.
Claim 12
Dependent Claim
9 words
The (+), (-) and (±) forms of 3'-phenoxybenzyl 1-(2-naphthyl)-2,2,3,3-tetrafluorocyclobutane-carboxylate.
Claim 13
Dependent Claim
9 words
The (+), (-) and (±) forms of 3'-phenoxybenzyl 1-(2-naphthyl)-2,2,3,3-tetrafluorocyclobutane-carboxylate.
Claim 14
Dependent Claim
8 words
(+), (-) and (±) forms of α-cyano-3'-phenoxybenzyl 1-(2-naphthyl)-2,2,3,3-tetrafluorocyclobutanecarboxylate.
Claim 15
Dependent Claim
8 words
(+), (-) and (±) forms of α-cyano-3'-phenoxybenzyl 1-(2-naphthyl)-2,2,3,3-tetrafluorocyclobutanecarboxylate.
Claim 16
Dependent Claim
9 words
The (+), (-) and (±) forms of α-cyano-3'-phenyxybenzyl 3,3-difluoro-1-(2-naphthyl)-cyclobutanecarboxylate.
Claim 17
Dependent Claim
9 words
The (+), (-) and (±) forms of α-cyano-3'-phenyxybenzyl 3,3-difluoro-1-(2-naphthyl)-cyclobutanecarboxylate.
Claim 18
Dependent Claim
45 words
Insecticidal compositions, characterised in that they comprise an insecticidally effective amount of one or more of the compounds of formula I, as stated in claim 1, where R is one of the groups (a) to (f), incorporated in a suitable inert liquid or solid carrier.
Claim 19
Dependent Claim
27 words
Insecticidal compositions as claimed in claim 14, characterised in that they additionally contain at least one synergistic or potentiating agent of the class of microsomal oxidase inhibitors.
Claim 20
Dependent Claim
18 words
Insecticidal compositions as claimed in claim 15, characterised in that the synergist or potentiator is a pyrethrin synergist.
Claim 21
Dependent Claim
22 words
Insecticidal compositions as claimed in claim 15, characterised in that 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)-4-[2-(octylsulfinyl)propyl]benzene; dipropyl-5,6,7,8-tetrahydro-7-methylnaphtho-[2,3-d]-1,3-dioxole-5,6-dicarboxylate.
Claim 22
Dependent Claim
32 words
Insecticidal compositions as claimed in claim 15, characterised in that the synergist is "Sesoxane" or piperonyl butoxide used in an amount from 1/1000th to 5 times the weight of the compound I.
Claim 23
Dependent Claim
34 words
Insecticidal compositions as claimed in claim 15, characterised in that the amount of Sesoxane or piperonyl butoxide used is from about 1/100th to an equal part by weight per part of the compound I.
Claim 24
Dependent Claim
26 words
A method of controlling insects comprising applying an insecticidally effective amount of a compound of the formula of claim 1 to an area requiring insect control.
Claim 25
Independent Claim
28 words
A method of controlling insects comprising applying an insecticidally effective amount of the composition of claims 14, 15, 17, 18 or 19 to an area requiring insect control.
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) | 1984-07-06 | 1985-01-05 | 1985-07-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-07-06 | 1989-01-05 | 1989-07-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-07-06 | 1993-01-05 | 1993-07-07 | $7700.00 | Window Closed / Lapsed |