US4190651A
Expired / Lapsed
US
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Cyclic phosphoric acid amide esters, and an insecticide containing the same as active ingredient
Assignee: KH Neochem Co Ltd
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Filing: 1978-03-08
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Granted: 1980-02-26
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Expires: 1998-03-08
Abstract
Abstract The present invention relates to novel cyclic phosphoric acid amide esters, a process for producing the same and an insecticide containing the same as active ingredient. The present invention provides novel 4-substituted-1,3,2-oxazaphospholidine derivatives of the general formula: <IMAGE> I wherein R1 represents an alkyl, alkenyl, alkynyl, aralkyl, aralkenyl or aralkynyl group and R2 represents an alkyl group. The compounds of the formula I may be produced by the reaction of a compound of the formula: <IMAGE> II wherein R1 is as hereinbefore defined or an alcoholate thereof with a compound of the formula: <IMAGE> III wherein R2 is as hereinbefore defined and X1 and X2, which may be same or different, each represents an atom or group removable as an anion. The compounds of the formula I have interesting insecticidal activity particularly against houseflies, adzuki-been weevil, mulberry mealy bug etc.
Inventors
- 👤 Morifusa Eto
- 👤 Shinkichi Tawata
- 👤 Kohei Oshima
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 02:40
CPC Classifications
A; A01; A01N; A01N57/00; A01N57/36; C; C07; C07F; C07F9/00; C07F9/02; C07F9/547; C07F9/6564; C07F9/6581; C07F9/6584; C07F9/65842; C07F9/65844
Claims Analysis
Total Claims: 29
Claim 1
Independent Claim
33 words
Compounds of the general formula: ##STR23## wherein R 1 is one member selected from the class consisting of alkyl, alkenyl, alkynyl, aralkyl, aralkenyl and aralkynyl groups and R 2 is an alkyl group.
Claim 2
Dependent Claim
33 words
Compounds of the general formula: ##STR23## wherein R 1 is one member selected from the class consisting of alkyl, alkenyl, alkynyl, aralkyl, aralkenyl and aralkynyl groups and R 2 is an alkyl group.
Claim 3
Dependent Claim
93 words
Compounds of claim 1 wherein R 1 is one member selected from the class consisting of alkyl, alkenyl and alkynyl groups, each having not more than 6 carbon atoms, and aralkyl, aralkenyl and aralkynyl groups, each having carbon atoms of 7 to 11, the aryl moiety of which may optionally be substitued by at least one member selected from the class consisting of alkyl and alkoxy groups, each having carbon atoms of from 1 to 4, and a halogen atom and R 2 represents an alkyl group with 1 to 6 carbon atoms.
Claim 4
Dependent Claim
42 words
Compunds of claim 1 wherein R 1 represents one member selected from the class consisting of an alkyl group with 1 to 4 carbon atoms and a benzyl group and R 2 represents an alkyl group with 1 to 3 carbon atoms.
Claim 5
Dependent Claim
12 words
Compounds of claim 1 in the form of an optically active isomer.
Claim 6
Dependent Claim
40 words
A method of preventing or inhibiting the growth of proliferation of insects which comprises applying to a site infested with or susceptible to infestation by insects an effective amount of a compound of formula I as defined in claim 1.
Claim 7
Dependent Claim
92 words
Compound of the general formula: ##STR24## wherein R 1 represents one member selected from the class consisting of alkyl, alkenyl and alkynyl groups, each having not more than 6 carbon atoms, and aralkyl, aralkenyl and aralkynyl groups, each having 7 to 11 carbon atoms, the aryl moiety of which may optionally be substituted by at least one member selected from the class consisting of alkyl and alkoxy groups, each having 1 to 4 carbon atoms, and a halogen atom and R 2 represents an alkyl group with 1 to 6 carbon atoms.
Claim 8
Dependent Claim
92 words
Compound of the general formula: ##STR24## wherein R 1 represents one member selected from the class consisting of alkyl, alkenyl and alkynyl groups, each having not more than 6 carbon atoms, and aralkyl, aralkenyl and aralkynyl groups, each having 7 to 11 carbon atoms, the aryl moiety of which may optionally be substituted by at least one member selected from the class consisting of alkyl and alkoxy groups, each having 1 to 4 carbon atoms, and a halogen atom and R 2 represents an alkyl group with 1 to 6 carbon atoms.
Claim 9
Dependent Claim
1 words
(4S)-2-Ethoxy-4-methyl-1,3,2-oxazaphospholidine-2-sulphide.
Claim 10
Dependent Claim
1 words
(4S)-2-Ethoxy-4-methyl-1,3,2-oxazaphospholidine-2-sulphide.
Claim 11
Dependent Claim
1 words
2-Ethoxy-4-ethyl-1,3,2-oxazaphospholidine-2-sulphide.
Claim 12
Dependent Claim
1 words
2-Ethoxy-4-ethyl-1,3,2-oxazaphospholidine-2-sulphide.
Claim 13
Dependent Claim
1 words
(4S)-2-Methoxy-4-isopropyl-1,3,2-oxazaphospholidine-2-sulphide.
Claim 14
Dependent Claim
1 words
(4S)-2-Methoxy-4-isopropyl-1,3,2-oxazaphospholidine-2-sulphide.
Claim 15
Dependent Claim
1 words
(4S)-2-Ethoxy-4-isopropyl-1,3,2-oxazaphospholidine-2-sulphide.
Claim 16
Dependent Claim
1 words
(4S)-2-Ethoxy-4-isopropyl-1,3,2-oxazaphospholidine-2-sulphide.
Claim 17
Dependent Claim
1 words
(4S)-2-Ethoxy-4-sec-butyl-1,3,2-oxazaphospholidine-2-sulphide.
Claim 18
Dependent Claim
1 words
(4S)-2-Ethoxy-4-sec-butyl-1,3,2-oxazaphospholidine-2-sulphide.
Claim 19
Dependent Claim
1 words
(4S)-2-Methoxy-4-isobutyl-1,3,2-oxazaphospholidine-2-sulphide.
Claim 20
Dependent Claim
1 words
(4S)-2-Methoxy-4-isobutyl-1,3,2-oxazaphospholidine-2-sulphide.
Claim 21
Dependent Claim
1 words
(4S)-2-Ethoxy-4-isobutyl-1,3,2-oxazaphospholidine-2-sulphide.
Claim 22
Dependent Claim
1 words
(4S)-2-Ethoxy-4-isobutyl-1,3,2-oxazaphospholidine-2-sulphide.
Claim 23
Dependent Claim
1 words
(4S)-2-Ethoxy-4-benzyl-1,3,2-oxazaphospholidine-2-sulphide.
Claim 24
Dependent Claim
1 words
(4S)-2-Ethoxy-4-benzyl-1,3,2-oxazaphospholidine-2-sulphide.
Claim 25
Dependent Claim
1 words
(4R)-2-Methoxy-4-isobutyl-1,3,2-oxazaphospholidine-2-sulphide.
Claim 26
Dependent Claim
1 words
(4R)-2-Methoxy-4-isobutyl-1,3,2-oxazaphospholidine-2-sulphide.
Claim 27
Dependent Claim
31 words
Insecticidal compositions comprising as active ingredient at least one compound of the formula I as defined in claim 1 in association with one member selected from an inert carrier and diluent.
Claim 28
Dependent Claim
16 words
Compositions of claim 16 in one form selected from powders, wettable powders, emulsifiable concentrates and granules.
Claim 29
Dependent Claim
14 words
Compositions of claim 16 containing from 0.01 to 1% by weight of active ingredient.
References Cited (Backward Citations)
GB763485A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-02-25 | 1983-08-27 | 1984-02-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-02-25 | 1987-08-27 | 1988-02-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-02-25 | 1991-08-27 | 1992-02-26 | $7700.00 | Window Closed / Lapsed |