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US4080443A
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(Substituted pyridyl)phenoxy phosphorous compounds and their use as insecticides
Assignee: LAir Liquide SA pour lEtude et lExploitation des Procedes Georges Claude
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Filing: 1976-12-02
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Granted: 1978-03-21
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Expires: 1996-12-02
Abstract
Abstract Compounds are prepared which correspond to the formula ##STR1## wherein each X independently represents chloro, fluoro or bromo; X' represents hydrogen, methyl, chloro, fluoro or bromo; G represents oxygen or sulfur; Z represents oxygen, sulfur, sulfinyl or sulfonyl, with the proviso that Z is attached to the pyridine ring in only the 2 or 4 ring position; D represents cyano, nitro, trifluoromethyl, loweralkyl, loweralkoxy, loweralkylsulfonyl, loweralkylthio, or the radical ##STR2## R represents loweralkoxy, loweralkylamino or diloweralkylamino; R' represents R or phenyl; m represents an integer of from 0 to 4; n represents 0 or 1 and the sum of m + n represents an integer of from 0 to 4. The compounds have been found to be effective insect control agents.
Inventors
- 👤 Sudarshan K. Malhotra
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 16:11
CPC Classifications
C; C07; C07F; C07F9/00; C07F9/02; C07F9/547; C07F9/553; C07F9/576; C07F9/58; C10; C10M; C10M2223/00; C10M2223/02; C10M2223/04; C10M2223/042; C10M2223/047; C10M2223/06; C10M2223/065; C10N; C10N2040/00; C10N2040/20; C10N2040/22
Claims Analysis
Total Claims: 59
Claim 1
Independent Claim
141 words
A compound corresponding to the formula ##STR29## wherein each X independently represents chloro, fluoro or bromo; X' represents hydrogen, methyl, chloro, bromo or fluoro; G represents oxygen or sulfur; Z represents oxygen, sulfur, sulfinyl or sulfonyl, with the proviso that Z is attached to the pyridine ring is only the 2 or 4 ring position; D represents nitro, trifluoromethyl, loweralkyl of 1 to 4 carbon atoms, loweralkoxy of 1 to 4 carbon atoms, loweralkylthio of 1 to 4 carbon atoms or loweralkylsulfonyl of 1 to 4 carbon atoms; R represents loweralkylthio, loweralkoxy, loweralkylamino of 1 to 4 carbon atoms or diloweralkylamino of 1 to 4 carbon atoms; R' represents R or phenyl; m represents an integer of from 0 to 4; n represents 0 or 1 and the sum of m + n represents an integer of from 0 to 4.
Claim 2
Dependent Claim
141 words
A compound corresponding to the formula ##STR29## wherein each X independently represents chloro, fluoro or bromo; X' represents hydrogen, methyl, chloro, bromo or fluoro; G represents oxygen or sulfur; Z represents oxygen, sulfur, sulfinyl or sulfonyl, with the proviso that Z is attached to the pyridine ring is only the 2 or 4 ring position; D represents nitro, trifluoromethyl, loweralkyl of 1 to 4 carbon atoms, loweralkoxy of 1 to 4 carbon atoms, loweralkylthio of 1 to 4 carbon atoms or loweralkylsulfonyl of 1 to 4 carbon atoms; R represents loweralkylthio, loweralkoxy, loweralkylamino of 1 to 4 carbon atoms or diloweralkylamino of 1 to 4 carbon atoms; R' represents R or phenyl; m represents an integer of from 0 to 4; n represents 0 or 1 and the sum of m + n represents an integer of from 0 to 4.
Claim 3
Dependent Claim
11 words
The compound as defined in claim 1 wherein D is nitro.
Claim 4
Dependent Claim
11 words
The compound as defined in claim 1 wherein D is trifluoromethyl.
Claim 5
Dependent Claim
11 words
The compound as defined in claim 3 which is O,O-diethyl O-[4-((6-(trifluoromethyl)-2-pyridyl)thio)-phenyl]phosphorothioate.
Claim 6
Dependent Claim
11 words
The compound as defined in claim 3 which is O,O-diethyl O-[4-((6-(trifluoromethyl)-2-pyridyl)thio)-phenyl]phosphate.
Claim 7
Dependent Claim
11 words
The compound as defined in claim 3 which is O,O-dimethyl O-[4-((6-(trifluoromethyl)-2-pyridyl)thio)-phenyl]phosphorothioate.
Claim 8
Dependent Claim
11 words
The compound as defined in claim 1 wherein D is loweralkyl.
Claim 9
Dependent Claim
11 words
The compound as defined in claim 1 wherein D is loweralkoxy.
Claim 10
Dependent Claim
11 words
The compound as defined in claim 8 which is O,O-diethyl O-[4-((6-methoxy-2-pyridyl)thio)phenyl]-phosphorothioate.
Claim 11
Dependent Claim
11 words
The compound as defined in claim 1 wherein D is loweralkylthio.
Claim 12
Dependent Claim
13 words
The compound as defined in claim 1 wherein D is the radical ##STR30##
Claim 13
Dependent Claim
12 words
The compound as defined in claim 1 wherein D is loweralkyl sulfonyl.
Claim 14
Dependent Claim
11 words
The compound as defined in claim 1 wherein n is 0.
Claim 15
Dependent Claim
11 words
The compound as defined in claim 13 which is O,O-diethyl O-[4-((2-pyridyl)thio)phenyl]phosphorothioate.
Claim 16
Dependent Claim
11 words
The compound as defined in claim 13 which is O,O-diethyl O-[4-((6-chloro-2-pyridyl)thio)phenyl]-phosphorothioate.
Claim 17
Dependent Claim
11 words
The compound as defined in claim 13 which is O,O-diethyl O-[4-((3-chloro-2-pyridyl)thio)phenyl]phosphorothioate.
Claim 18
Dependent Claim
11 words
The compound as defined in claim 13 which is O,O-diethyl O-[2-chloro-4-((6-fluoro-2-pyridyl)thio)phenyl]-phosphorothioate.
Claim 19
Dependent Claim
11 words
The compound as defined in claim 13 which is O,O-diethyl O-[2-chloro-4-((3-chloro-2-pyridyl)thio)-phenyl]phosphorothioate.
Claim 20
Dependent Claim
11 words
The compound as defined in claim 13 which is O,O-diethyl O-[2-((6-chloro-2-pyridyl)thio)phenyl)]phosphorothioate.
Claim 21
Dependent Claim
161 words
An insecticidal composition comprising as an active ingredient, an insecticidally-effective amount of a compound corresponding to the formula ##STR31## wherein each X independently represents chloro, fluoro or bromo; X' represents hydrogen, methyl, chloro, bromo or fluoro; G represents oxygen or sulfur; Z represents oxygen, sulfur, sulfinyl or sulfonyl, with the proviso that Z is attached to the pyridine ring in only the 2 or 4 ring position; D represents nitro, trifluoromethyl, loweralkyl of 1 to 4 carbon atoms, loweralkoxy of 1 to 4 carbon atoms, loweralkylthio of 1 to 4 carbon atoms or loweralkylsulfonyl of 1 to 4 carbon atoms; R represents loweralkylthio, loweralkoxy, loweralkylamino of 1 to 4 carbon atoms or diloweralkylamino of 1 to 4 carbon atoms; R' represents R or phenyl; m represents an integer of from 0 to 4; n represents 0 or 1 and the sum of m + n represents an integer of from 0 to 4, in intimate admixture with an inert carrier therefor.
Claim 22
Dependent Claim
161 words
An insecticidal composition comprising as an active ingredient, an insecticidally-effective amount of a compound corresponding to the formula ##STR31## wherein each X independently represents chloro, fluoro or bromo; X' represents hydrogen, methyl, chloro, bromo or fluoro; G represents oxygen or sulfur; Z represents oxygen, sulfur, sulfinyl or sulfonyl, with the proviso that Z is attached to the pyridine ring in only the 2 or 4 ring position; D represents nitro, trifluoromethyl, loweralkyl of 1 to 4 carbon atoms, loweralkoxy of 1 to 4 carbon atoms, loweralkylthio of 1 to 4 carbon atoms or loweralkylsulfonyl of 1 to 4 carbon atoms; R represents loweralkylthio, loweralkoxy, loweralkylamino of 1 to 4 carbon atoms or diloweralkylamino of 1 to 4 carbon atoms; R' represents R or phenyl; m represents an integer of from 0 to 4; n represents 0 or 1 and the sum of m + n represents an integer of from 0 to 4, in intimate admixture with an inert carrier therefor.
Claim 23
Dependent Claim
15 words
The composition as defined in claim 20 wherein in the active ingredient D is nitro.
Claim 24
Dependent Claim
15 words
The composition as defined in claim 20 wherein in the active ingredient, D is trifluoromethyl.
Claim 25
Dependent Claim
14 words
The composition as defined in claim 22 wherein the active ingredient is O,O-diethyl O-[4-((6-(trifluoromethyl)-2-pyridyl)thio)phenyl]phosphorothioate.
Claim 26
Dependent Claim
14 words
The composition as defined in claim 22 wherein the active ingredient is O,O-diethyl O[4-((6-(trifluoromethyl)-2-pyridyl)thio)phenyl]phosphate.
Claim 27
Dependent Claim
14 words
The composition as defined in claim 22 wherein the active ingredient is O,O-dimethyl O-[4-((6-(trifluoromethyl)-2-pyridyl)thio)phenyl]phosphorothioate.
Claim 28
Dependent Claim
15 words
The composition as defined in claim 20 wherein in the active ingredient D is loweralkyl.
Claim 29
Dependent Claim
15 words
The composition as defined in claim 20 wherein in the active ingredient D is loweralkoxy.
Claim 30
Dependent Claim
14 words
The composition as defined in claim 27 wherein the active ingredient is O,O-diethyl O-[4-((6-methoxy-2-pyridyl)thio)phenyl]phosphorothioate.
Claim 31
Dependent Claim
15 words
The composition as defined in claim 20 wherein in the active ingredient D is loweralkythio.
Claim 32
Dependent Claim
17 words
The composition as defined in claim 21 wherein in the active ingredient D is the radical ##STR32##
Claim 33
Dependent Claim
16 words
The composition as defined in claim 20 wherein in the active ingredient D is loweralkyl sulfonyl.
Claim 34
Dependent Claim
15 words
The composition as defined in claim 20 wherein in the active ingredient n is 0.
Claim 35
Dependent Claim
14 words
The composition as defined in claim 32 wherein the active ingredient is O,O-diethyl O-[4-((2-pyridyl)thio)phenyl]phosphorothioate.
Claim 36
Dependent Claim
14 words
The composition as defined in claim 32 wherein the active ingredient is O,O-diethyl O-[4-((6-chloro-2-pyridyl)thio)phenyl]phosphorothioate.
Claim 37
Dependent Claim
14 words
The composition as defined in claim 32 wherein the active ingredient is O,O-diethyl O-[4-((3-chloro-2-pyridyl)thio)phenyl]phosphorothioate.
Claim 38
Dependent Claim
14 words
The composition as defined in claim 32 wherein the active ingredient is O,O-diethyl O-[2-chloro-4-((6-fluoro-2-pyridyl)thio)phenyl]phosphorothioate.
Claim 39
Dependent Claim
14 words
The composition as defined in claim 32 wherein the active ingredients is O,O-diethyl O-[2-chloro-4-((3-chloro-2-pyridyl)thio)phenyl]phosphorothioate.
Claim 40
Dependent Claim
14 words
The composition as defined in claim 32 wherein the active ingredient is O,O-diethyl O-[2-((6-chloro-2-pyridyl)thio)phenyl]phosphorothioate.
Claim 41
Independent Claim
178 words
A method for the kill and control of insects which comprises contacting said insects or their habitat with a composition containing as the active ingredient an insecticidally-effective amount of a compound corresponding to the formula ##STR33## wherein each X independently represents chloro, fluoro or bromo; X' represents hydrogen, methyl, chloro, bromo or fluoro; G represents oxygen or sulfur; Z represents oxygen, sulfur, sulfinyl or sulfonyl, with the proviso that Z is attached to the pyridine ring in only the 2 or 4 ring position; D represents nitro, trifluoromethyl, loweralkyl of 1 to 4 carbon atoms, loweralkoxy of 1 to 4 carbon atoms, loweralkylthio of 1 to 4 carbon atoms or loweralkylsulfonyl of 1 to 4 carbon atoms; R represents loweralkylthio, loweralkoxy, loweralkylamino of 1 to 4 carbon atoms or diloweralkylamino of 1 to 4 carbon atoms; R' represents R or phenyl; m represents an integer of from 0 to 4; n represents 0 or 1 and the sum of m + n represents an integer of from 0 to 4, in intimate admixture with an inert carrier therefor.
Claim 42
Independent Claim
178 words
A method for the kill and control of insects which comprises contacting said insects or their habitat with a composition containing as the active ingredient an insecticidally-effective amount of a compound corresponding to the formula ##STR33## wherein each X independently represents chloro, fluoro or bromo; X' represents hydrogen, methyl, chloro, bromo or fluoro; G represents oxygen or sulfur; Z represents oxygen, sulfur, sulfinyl or sulfonyl, with the proviso that Z is attached to the pyridine ring in only the 2 or 4 ring position; D represents nitro, trifluoromethyl, loweralkyl of 1 to 4 carbon atoms, loweralkoxy of 1 to 4 carbon atoms, loweralkylthio of 1 to 4 carbon atoms or loweralkylsulfonyl of 1 to 4 carbon atoms; R represents loweralkylthio, loweralkoxy, loweralkylamino of 1 to 4 carbon atoms or diloweralkylamino of 1 to 4 carbon atoms; R' represents R or phenyl; m represents an integer of from 0 to 4; n represents 0 or 1 and the sum of m + n represents an integer of from 0 to 4, in intimate admixture with an inert carrier therefor.
Claim 43
Dependent Claim
15 words
The method as defined in claim 39 wherein in the active ingredient D is nitro.
Claim 44
Dependent Claim
15 words
The method as defined in claim 39 wherein in the active ingredient D is trifluoromethyl.
Claim 45
Dependent Claim
14 words
The method as defined in claim 41 wherein the active ingredient is O,O-diethyl O-[4-((6-(trifluoromethyl)-2-pyridyl)thio)phenyl]phosphorothioate.
Claim 46
Dependent Claim
14 words
The method as defined in claim 41 wherein the active ingredient is O,O-diethyl O-[4-((6-(trifluoromethyl)-2-pyridyl)thio)phenyl]phosphate.
Claim 47
Dependent Claim
14 words
The method as defined in claim 41 wherein the active ingredient is O,O-dimethyl O-[4-((6-(trifluoromethyl)-2-pyridyl)thio)phenyl]phosphorothioate.
Claim 48
Dependent Claim
15 words
The method as defined in claim 39 wherein in the active ingredient D is loweralkyl.
Claim 49
Dependent Claim
15 words
The method as defined in claim 39 wherein in the active ingredient D is loweralkoxy.
Claim 50
Dependent Claim
14 words
The method as defined in claim 46 wherein the active ingredient is O,O-diethyl O-[4-((6-methoxy-2-pyridyl)thio)phenyl]phosphorothioate.
Claim 51
Dependent Claim
15 words
The method as defined in claim 39 wherein in the active ingredient D is loweralkylthio.
Claim 52
Dependent Claim
16 words
The method as defined in claim 39 wherein in the active ingredient D is loweralkyl sulfonyl.
Claim 53
Dependent Claim
15 words
The method as defined in claim 39 wherein in the active ingredient n is 0.
Claim 54
Dependent Claim
14 words
The method as defined in claim 50 wherein the active ingredient is O,O-diethyl O-[4-((2-pyridyl)thio)-phenyl]phosphorothioate.
Claim 55
Dependent Claim
14 words
The method as defined in claim 50 wherein the active ingredient is O,O-diethyl O-[4-((6-chloro-2-pyridyl)-thio)phenyl]phosphorothioate.
Claim 56
Dependent Claim
14 words
The method as defined in claim 50 wherein the active ingredient is O,O-diethyl O-[4-((3-chloro-2-pyridyl)-thio)phenyl]phosphorothioate.
Claim 57
Dependent Claim
14 words
The method as defined in claim 50 wherein the active ingredient is O,O-diethyl O-[2-chloro-4-((6-fluoro-2-pyridyl)thio)phenyl]phosphorothioate.
Claim 58
Dependent Claim
14 words
The method as defined in claim 50 wherein the active ingredient is O,O-diethyl O-[2-chloro-4-((3-chloro-2-pyridyl)thio)phenyl]phosphorothioate.
Claim 59
Dependent Claim
14 words
The method as defined in claim 50 wherein the active ingredient is O,O-diethyl O-[2-((6-chloro-2-pyridyl)thio)phenyl]phosphorothioate.
References Cited (Backward Citations)
US3968222A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-03-20 | 1981-09-19 | 1982-03-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-03-20 | 1985-09-19 | 1986-03-21 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-03-20 | 1989-09-19 | 1990-03-21 | $7700.00 | Window Closed / Lapsed |