US4062968A
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Insecticidal substituted acetate compounds
Assignee: Sumitomo Chemical Co Ltd
•
Filing: 1975-07-16
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Granted: 1977-12-13
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Expires: 1995-07-16
Abstract
Abstract Substituted acetate compounds represented by the formula <IMAGE> which are useful as pesticides and pesticidal composition containing the substituted acetate compounds as active ingredients, as well as processes for preparing the compounds and the compositions are disclosed.
Inventors
- 👤 Keimei Fujimoto
- 👤 Nobuo Ohno
- 👤 Yoshitoshi Okuno
- 👤 Toshio Mizutani
- 👤 Isao Ohno
- 👤 Masachika Hirano
- 👤 Nobushige Itaya
- 👤 Takashi Matsuo
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 21:42
CPC Classifications
C; C07; C07D; C07D307/00; C07D307/02; C07D307/34; C07D307/38; C07D307/54; C07C; C07C323/00
Claims Analysis
Total Claims: 51
Claim 1
Independent Claim
334 words
A substituted acetate compound of the formula ##STR769## wherein Y is selected from the group consisting of the formulae: ##STR770## in which R 1 and R 2 are individually hydrogen, halogen, cyano, nitro, lower alkyl, lower alkenyl, lower alkynyl, lower alkoxy, lower alkoxyalkyl, halogen-substituted lower alkyl, halogen-substituted lower alkenyl, halogen-substituted lower alkynyl, lower alkylthio, lower alkylsulfoxyl, C 2 -C 4 alkanoyl, C 2 alkanoyloxy, lower alkoxycarbonyl, lower alkenyloxycarbonyl, lower alkynyloxycarbonyl, methylenedioxy, tetramethylene or trimethylene group R 3 and R 4 are individually hydrogen, halogen, cyano, nitro, lower alkyl, lower alkenyl, lower alkynyl, lower alkoxy, lower alkoxyalkyl, halogen-substituted lower alkyl, halogen-substituted lower alkenyl, halogen-substituted lower alkynyl, lower alkylthio, lower alkylsulfoxyl, C 2 -C 4 alkanoyl, lower alkoxycarbonyl, lower alkenyloxycarbonyl or lower alkynyloxycarbonyl group; A represents an oxygen atom or a sulfur atom; R 5 represents hydrogen, halogen, cyano, nitro or lower alkyl group; m is an integer of from 1 to 3; R 6 represents hydrogen, halogen, cyano, nitro or lower alkyl group; n is an integer of from 1 to 3; and the dotted line in the formula (V) represents a double bond present at a position conjugated or non-conjugated with the ketone (C=O), or Y represents a substituted ethylene group of the formula (VI) ##STR771## in which R 7 , R 8 and R 9 constitutes a plane together with the double bond at β-γ position of the ester group, and are individually hydrogen, lower alkyl, lower alkenyl, lower alkynyl, halogen, Z represents a straight or branched lower alkyl, lower alkenyl, lower alkynyl, lower alkoxy, cyano, halogen-substituted lower alkyl, halogen-substituted lower alkenyl group or an alicyclic group having 3 to 7 carbon atoms; in which R 10 represents an allyl, propargyl, benzyl, thenyl, furylmethyl, phenoxy or phenylthio group; R 11 represents hydrogen, methyl, trifluoromethyl or halogen R 10 and R 11 may, when they are bonded to each other at terminals, form a trimethylene or tetramethylene group; R 12 represents hydrogen, ethynyl or cyano; t is an integer of from 1 to 2.
Claim 2
Dependent Claim
334 words
A substituted acetate compound of the formula ##STR769## wherein Y is selected from the group consisting of the formulae: ##STR770## in which R 1 and R 2 are individually hydrogen, halogen, cyano, nitro, lower alkyl, lower alkenyl, lower alkynyl, lower alkoxy, lower alkoxyalkyl, halogen-substituted lower alkyl, halogen-substituted lower alkenyl, halogen-substituted lower alkynyl, lower alkylthio, lower alkylsulfoxyl, C 2 -C 4 alkanoyl, C 2 alkanoyloxy, lower alkoxycarbonyl, lower alkenyloxycarbonyl, lower alkynyloxycarbonyl, methylenedioxy, tetramethylene or trimethylene group R 3 and R 4 are individually hydrogen, halogen, cyano, nitro, lower alkyl, lower alkenyl, lower alkynyl, lower alkoxy, lower alkoxyalkyl, halogen-substituted lower alkyl, halogen-substituted lower alkenyl, halogen-substituted lower alkynyl, lower alkylthio, lower alkylsulfoxyl, C 2 -C 4 alkanoyl, lower alkoxycarbonyl, lower alkenyloxycarbonyl or lower alkynyloxycarbonyl group; A represents an oxygen atom or a sulfur atom; R 5 represents hydrogen, halogen, cyano, nitro or lower alkyl group; m is an integer of from 1 to 3; R 6 represents hydrogen, halogen, cyano, nitro or lower alkyl group; n is an integer of from 1 to 3; and the dotted line in the formula (V) represents a double bond present at a position conjugated or non-conjugated with the ketone (C=O), or Y represents a substituted ethylene group of the formula (VI) ##STR771## in which R 7 , R 8 and R 9 constitutes a plane together with the double bond at β-γ position of the ester group, and are individually hydrogen, lower alkyl, lower alkenyl, lower alkynyl, halogen, Z represents a straight or branched lower alkyl, lower alkenyl, lower alkynyl, lower alkoxy, cyano, halogen-substituted lower alkyl, halogen-substituted lower alkenyl group or an alicyclic group having 3 to 7 carbon atoms; in which R 10 represents an allyl, propargyl, benzyl, thenyl, furylmethyl, phenoxy or phenylthio group; R 11 represents hydrogen, methyl, trifluoromethyl or halogen R 10 and R 11 may, when they are bonded to each other at terminals, form a trimethylene or tetramethylene group; R 12 represents hydrogen, ethynyl or cyano; t is an integer of from 1 to 2.
Claim 3
Dependent Claim
111 words
A compound of the formula ##STR772## wherein R 1 is a member selected from the group consisting of hydrogen, methoxy, ethoxy, acetoxy, methylsulfinyl, C 1 -C 4 alkyl, trifluoromethyl, allyl, acetyl, ethoxycarbonyl, methylenedioxy, methylthio, trimethylene, tetramethylene, chlorine, fluorine, iodine, isopropenyl, propargyl, methoxymethyl, ethoxymethyl, chloroethylene, chloroallyl, butyryl, butylthio, allyloxycarbonyl, nitro and methoxycarbonyl; R 2 is a member selected from the group consisting of hydrogen, methyl, methoxy, chlorine and bromine; R 3 is hydrogen or methyl; Z is a member selected from the group consisting of C 1 -C 4 alkyl, ethoxy, allyl, bromoethyl, cyclohexyl, cyclopropylmethyl, isopropenyl, propargyl, trifluoromethyl and cyano; and X is a member selected from the group consisting of: ##STR773##
Claim 4
Dependent Claim
111 words
A compound of the formula ##STR772## wherein R 1 is a member selected from the group consisting of hydrogen, methoxy, ethoxy, acetoxy, methylsulfinyl, C 1 -C 4 alkyl, trifluoromethyl, allyl, acetyl, ethoxycarbonyl, methylenedioxy, methylthio, trimethylene, tetramethylene, chlorine, fluorine, iodine, isopropenyl, propargyl, methoxymethyl, ethoxymethyl, chloroethylene, chloroallyl, butyryl, butylthio, allyloxycarbonyl, nitro and methoxycarbonyl; R 2 is a member selected from the group consisting of hydrogen, methyl, methoxy, chlorine and bromine; R 3 is hydrogen or methyl; Z is a member selected from the group consisting of C 1 -C 4 alkyl, ethoxy, allyl, bromoethyl, cyclohexyl, cyclopropylmethyl, isopropenyl, propargyl, trifluoromethyl and cyano; and X is a member selected from the group consisting of: ##STR773##
Claim 5
Dependent Claim
54 words
A compound of the formula; ##STR774## wherein R 3 is a member selected from the group consisting of hydrogen, methyl, allyl, methoxycarbonyl and acetyl; R 4 is hydrogen; Z is a member selected from the group consisting of ethyl, propyl and allyl; and X is a member selected from the group consisting of ##STR775##
Claim 6
Dependent Claim
54 words
A compound of the formula; ##STR774## wherein R 3 is a member selected from the group consisting of hydrogen, methyl, allyl, methoxycarbonyl and acetyl; R 4 is hydrogen; Z is a member selected from the group consisting of ethyl, propyl and allyl; and X is a member selected from the group consisting of ##STR775##
Claim 7
Dependent Claim
36 words
A compound of the formula; ##STR776## wherein R 3 is a member selected from the group consisting of hydrogen, methyl, allyl, methoxycarbonyl and butanoyl; R 4 is hydrogen; Z is ethyl or propyl; X is ##STR777##
Claim 8
Dependent Claim
36 words
A compound of the formula; ##STR776## wherein R 3 is a member selected from the group consisting of hydrogen, methyl, allyl, methoxycarbonyl and butanoyl; R 4 is hydrogen; Z is ethyl or propyl; X is ##STR777##
Claim 9
Dependent Claim
51 words
A compound of the formula; ##STR778## wherein R 7 is a member selected from the group consisting of hydrogen, methyl and ethyl; R 8 is hydrogen or methyl; R 9 is methyl; Z is C 1 -C 3 alkyl; and X is a member selected from the group consisting of ##STR779##
Claim 10
Dependent Claim
51 words
A compound of the formula; ##STR778## wherein R 7 is a member selected from the group consisting of hydrogen, methyl and ethyl; R 8 is hydrogen or methyl; R 9 is methyl; Z is C 1 -C 3 alkyl; and X is a member selected from the group consisting of ##STR779##
Claim 11
Dependent Claim
39 words
A compound of the formula; ##STR780## wherein R 5 is hydrogen or methyl; m is an integer of 1 or 2; Z is a member selected from the group consisting of methyl, propyl, allyl and propargyl; X is ##STR781##
Claim 12
Dependent Claim
39 words
A compound of the formula; ##STR780## wherein R 5 is hydrogen or methyl; m is an integer of 1 or 2; Z is a member selected from the group consisting of methyl, propyl, allyl and propargyl; X is ##STR781##
Claim 13
Dependent Claim
25 words
A compound of the formula; ##STR782## wherein R 6 is methyl, n is an integer of 1, Z is ethyl or propyl; X is ##STR783##
Claim 14
Dependent Claim
25 words
A compound of the formula; ##STR782## wherein R 6 is methyl, n is an integer of 1, Z is ethyl or propyl; X is ##STR783##
Claim 15
Dependent Claim
51 words
A phenylacetate compound of the formula ##STR784## wherein R' 1 represents a straight or branched chain alkyl having 1 to 4 carbon atoms, halogen or alkoxy having 1 to 4 carbon atoms; R' 2 represents hydrogen or a group which completes, together with R' 1 , methylenedioxy; and X' represents ##STR785##
Claim 16
Dependent Claim
51 words
A phenylacetate compound of the formula ##STR784## wherein R' 1 represents a straight or branched chain alkyl having 1 to 4 carbon atoms, halogen or alkoxy having 1 to 4 carbon atoms; R' 2 represents hydrogen or a group which completes, together with R' 1 , methylenedioxy; and X' represents ##STR785##
Claim 17
Dependent Claim
19 words
A phenylacetate compound of the formula ##STR786## wherein B represents a halogen atom, a lower alkyl group or methoxy.
Claim 18
Dependent Claim
19 words
A phenylacetate compound of the formula ##STR786## wherein B represents a halogen atom, a lower alkyl group or methoxy.
Claim 19
Dependent Claim
6 words
A compound of the formula ##STR787##
Claim 20
Dependent Claim
6 words
A compound of the formula ##STR787##
Claim 21
Dependent Claim
6 words
A compound of the formula ##STR788##
Claim 22
Dependent Claim
6 words
A compound of the formula ##STR788##
Claim 23
Dependent Claim
6 words
A compound of the formula ##STR789##
Claim 24
Dependent Claim
6 words
A compound of the formula ##STR789##
Claim 25
Dependent Claim
6 words
A compound of the formula ##STR790##
Claim 26
Dependent Claim
6 words
A compound of the formula ##STR790##
Claim 27
Dependent Claim
6 words
A compound of the formula ##STR791##
Claim 28
Dependent Claim
6 words
A compound of the formula ##STR791##
Claim 29
Dependent Claim
6 words
A compound of the formula ##STR792##
Claim 30
Dependent Claim
6 words
A compound of the formula ##STR792##
Claim 31
Dependent Claim
6 words
A compound of the formula ##STR793##
Claim 32
Dependent Claim
6 words
A compound of the formula ##STR793##
Claim 33
Dependent Claim
6 words
A compound of the formula ##STR794##
Claim 34
Dependent Claim
6 words
A compound of the formula ##STR794##
Claim 35
Dependent Claim
6 words
A compound of the formula, ##STR795##
Claim 36
Dependent Claim
6 words
A compound of the formula, ##STR795##
Claim 37
Dependent Claim
6 words
A compound of the formula, ##STR796##
Claim 38
Dependent Claim
6 words
A compound of the formula, ##STR796##
Claim 39
Dependent Claim
6 words
A compound of the formula, ##STR797##
Claim 40
Dependent Claim
6 words
A compound of the formula, ##STR797##
Claim 41
Dependent Claim
6 words
A compound of the formula, ##STR798##
Claim 42
Dependent Claim
6 words
A compound of the formula, ##STR798##
Claim 43
Dependent Claim
6 words
A compound of the formula ##STR799##
Claim 44
Dependent Claim
6 words
A compound of the formula ##STR799##
Claim 45
Dependent Claim
6 words
A compound of the formula ##STR800##
Claim 46
Dependent Claim
6 words
A compound of the formula ##STR800##
Claim 47
Dependent Claim
6 words
A compound of the formula ##STR801##
Claim 48
Dependent Claim
6 words
A compound of the formula ##STR801##
Claim 49
Dependent Claim
28 words
An insecticidal and miticidal composition comprising an insecticidally and miticidally effective amount of at least one substituted acetate compound as defined in claim 1 and an inert carrier.
Claim 50
Dependent Claim
50 words
An insecticidal and miticidal composition containing an insecticidally and miticidally effective amount of at least one substituted acetate compound as defined in claim 1 in the form of an emulsifiable concentrate, a wettable powder, a dust, a granule, a coating liquid, an oil preparation, an aerosol or a mosquito coil.
Claim 51
Dependent Claim
37 words
A method for controlling insects of the Order Coleoptera, Lepidoptera, Diptera, Orthoptera, Hemiptera, Homoptera and Acarus by applying an insecticidally effective amount of at least one substituted acetate compound as defined in claim 1 to their habitats.
References Cited (Backward Citations)
US3499087A
Cited
US3928364A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-12-12 | 1981-06-13 | 1981-12-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-12-12 | 1985-06-13 | 1985-12-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-12-12 | 1989-06-13 | 1989-12-13 | $7700.00 | Window Closed / Lapsed |