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US4029688A Expired / Lapsed US ⏱️ 0.0 years remaining

Carbamic pesticidal compositions

Assignee: Rhone Poulenc Nederland BV
•
Filing: 1974-06-27
•
Granted: 1977-06-14
•
Expires: 1994-06-27
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Abstract

Abstract Novel N-haloalkanesulfenylcarbamoyloxime compositions have been found to have exceptional miticidal and insecticidal activity.

Inventors

  • 👤 Themistocles D. J. D'Silva

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-04 01:10
CPC Classifications
A; A01; A01N; A01N47/00; A01N47/08; A01N47/10; A01N47/24

Claims Analysis

Total Claims: 23
Claim 1
Independent Claim 233 words
A compound of the formula: ##STR24## wherein: R is: lower alkyl or lower alkyl substituted with one or more lower alkoxy, lower alkylthio, lower alkylsulfinyl, lower alkylsulfonyl, phenylthio, phenylsulfinyl, phenylsulfonyl or R 4 CON(R 5 )--, all of which may be substituted with one or more cyano, nitro, azido, chloro, bromo or fluoro substituents R 1 is: hydrogen, chlorine, bromine, fluorine, cyano, substituted or unsubstituted lower alkyl having from 1 to 4 carbon atoms, substituted or unsubstituted lower alkylthio, substituted or unsubstituted lower alkoxy, substituted or unsubstituted lower carboalkoxyalkylthio, or substituted or unsubstituted lower alkylthioalkyl; wherein the permissible substituents may be one or more chloro, bromo, fluoro, cyano or nitro groups; R 2 is: lower alkyl or lower alkyl substituted with one or more chloro, bromo, fluoro, nitro, cyano, lower alkoxy or lower alkyl groups; R 3 is: perhalomethanesulfenyl or perhaloethanesulfenyl wherein the halogen substituents are chloro, bromo or fluoro; and R 4 is: hydrogen or lower alkyl; R 5 is: hydrogen or lower alkyl; and with the provisos that: a. when R is alkyl, R 1 is: substituted lower alkyl, substituted lower alkylthio, substituted or unsubstituted lower alkoxy, substituted or unsubstituted lower carboalkoxyalkylthio, or substituted or unsubstituted lower alkylthioalkyl; b. when R 1 is hydrogen, R is other than lower monoalkylthioalkyl; and c. a cyano group is present in at least one of the groups R, R 1 and R 2 .
Claim 2
Dependent Claim 233 words
A compound of the formula: ##STR24## wherein: R is: lower alkyl or lower alkyl substituted with one or more lower alkoxy, lower alkylthio, lower alkylsulfinyl, lower alkylsulfonyl, phenylthio, phenylsulfinyl, phenylsulfonyl or R 4 CON(R 5 )--, all of which may be substituted with one or more cyano, nitro, azido, chloro, bromo or fluoro substituents R 1 is: hydrogen, chlorine, bromine, fluorine, cyano, substituted or unsubstituted lower alkyl having from 1 to 4 carbon atoms, substituted or unsubstituted lower alkylthio, substituted or unsubstituted lower alkoxy, substituted or unsubstituted lower carboalkoxyalkylthio, or substituted or unsubstituted lower alkylthioalkyl; wherein the permissible substituents may be one or more chloro, bromo, fluoro, cyano or nitro groups; R 2 is: lower alkyl or lower alkyl substituted with one or more chloro, bromo, fluoro, nitro, cyano, lower alkoxy or lower alkyl groups; R 3 is: perhalomethanesulfenyl or perhaloethanesulfenyl wherein the halogen substituents are chloro, bromo or fluoro; and R 4 is: hydrogen or lower alkyl; R 5 is: hydrogen or lower alkyl; and with the provisos that: a. when R is alkyl, R 1 is: substituted lower alkyl, substituted lower alkylthio, substituted or unsubstituted lower alkoxy, substituted or unsubstituted lower carboalkoxyalkylthio, or substituted or unsubstituted lower alkylthioalkyl; b. when R 1 is hydrogen, R is other than lower monoalkylthioalkyl; and c. a cyano group is present in at least one of the groups R, R 1 and R 2 .
Claim 3
Dependent Claim 36 words
New compositions of matter in accordance with claim 1 wherein the total number of aliphatic carbon atoms in the substitutents R, R 1 , R 2 and R 3 does not exceed about ten carbon atoms.
Claim 4
Dependent Claim 18 words
A compound in accordance with claim 1 wherein R 2 is lower alkyl and R 3 is perhalomethanesulfenyl.
Claim 5
Dependent Claim 23 words
A compound in accordance with claim 1 wherein the cumulative sigma* value of the groups R and R 1 is at least 1.1.
Claim 6
Dependent Claim 13 words
A compound in accordance with claim 1 wherein R 1 is lower alkyl.
Claim 7
Dependent Claim 12 words
A compound in accordance with claim 1 wherein R 1 is hydrogen.
Claim 8
Dependent Claim 14 words
A compound in accordance with claim 1 wherein R 1 is substituted lower alkylthio.
Claim 9
Dependent Claim 20 words
A compound in accordance with claim 1 wherein R is lower alkyl substituted with one or more lower alkylthio groups.
Claim 10
Dependent Claim 15 words
A compound in accordance with claim 1 wherein R is a nitro substituted lower alkyl.
Claim 11
Dependent Claim 15 words
A compound in accordance with claim 1 wherein R is a cyano substituted lower alkyl.
Claim 12
Dependent Claim 12 words
A compound in accordance with claim 1 wherein R is lower alkysulfinylalkyl.
Claim 13
Dependent Claim 12 words
A compound in accordance with claim 1 wherein R is lower alkylsulfonyl.
Claim 14
Dependent Claim 2 words
2-Methyl-2-cyanopropionaldehyde (N-methyl-N-trichloromethanesulfenylcarbamoyl)oxime.
Claim 15
Dependent Claim 2 words
2-Methyl-2-cyanopropionaldehyde (N-methyl-N-trichloromethanesulfenylcarbamoyl)oxime.
Claim 16
Dependent Claim 1 words
2-Methyl-2-cyanopropionaldehyde(N-methyl-N-trifluoromethanesulfenylcarbamoyl)oxime.
Claim 17
Dependent Claim 1 words
2-Methyl-2-cyanopropionaldehyde(N-methyl-N-trifluoromethanesulfenylcarbamoyl)oxime.
Claim 18
Dependent Claim 2 words
1-(2-Cyanoethylthio)acetaldehyde O-(N-methyl-N-trichloromethanesulfenylcarbamoyl)oxime.
Claim 19
Dependent Claim 2 words
1-(2-Cyanoethylthio)acetaldehyde O-(N-methyl-N-trichloromethanesulfenylcarbamoyl)oxime.
Claim 20
Dependent Claim 120 words
A compound of the formula: ##STR25## wherein: R is lower alkyl R 1 is: substituted lower alkyl having from 1 to 4 carbon atoms, substituted lower alkylthio, substituted or unsubstituted lower alkoxy, substituted or unsubstituted lower carboalkoxyalkylthio, or substituted or unsubstituted lower alkylthioalkyl; wherein the permissible substituents may be one or more chloro, bromo, fluoro, cyano or nitro groups: R 2 is: lower alkyl or lower alkyl substituted with one or more chloro, bromo, fluoro, nitro, cyano, lower alkoxy or lower alkyl groups; R 3 is: perhalomethanesulfenyl or perhaloethanesulfenyl wherein the halogen substituents are chloro, bromo or fluoro; with the proviso that a cyano group is present in at least one of the groups R 1 and R 2 .
Claim 21
Dependent Claim 120 words
A compound of the formula: ##STR25## wherein: R is lower alkyl R 1 is: substituted lower alkyl having from 1 to 4 carbon atoms, substituted lower alkylthio, substituted or unsubstituted lower alkoxy, substituted or unsubstituted lower carboalkoxyalkylthio, or substituted or unsubstituted lower alkylthioalkyl; wherein the permissible substituents may be one or more chloro, bromo, fluoro, cyano or nitro groups: R 2 is: lower alkyl or lower alkyl substituted with one or more chloro, bromo, fluoro, nitro, cyano, lower alkoxy or lower alkyl groups; R 3 is: perhalomethanesulfenyl or perhaloethanesulfenyl wherein the halogen substituents are chloro, bromo or fluoro; with the proviso that a cyano group is present in at least one of the groups R 1 and R 2 .
Claim 22
Dependent Claim 125 words
A compound of the formula: ##STR26## wherein: R is: lower alkyl substituted with one or more lower alkoxy, lower alkylsulfinyl, lower alkylsulfonyl, phenylthio, phenylsulfinyl, phenylsulfonyl or R 4 CON(R 5 )--, all of which may be substituted with one or more cyano, nitro, azido, chloro, bromo or fluoro substitutents. R 2 is: lower alkyl or lower alkyl substituted with one or more chloro, bromo, fluoro, nitro, cyano, lower alkoxy or lower alkyl groups; R 3 is: perhalomethanesulfenyl or perhaloethanesulfenyl wherein the halogen substituents are chloro, bromo or fluoro; and R 4 is: hydrogen or lower alkyl; R 5 is: hydrogen or lower alkyl; and with the proviso that a cyano group is present in at least one of the groups R and R 2 .
Claim 23
Dependent Claim 125 words
A compound of the formula: ##STR26## wherein: R is: lower alkyl substituted with one or more lower alkoxy, lower alkylsulfinyl, lower alkylsulfonyl, phenylthio, phenylsulfinyl, phenylsulfonyl or R 4 CON(R 5 )--, all of which may be substituted with one or more cyano, nitro, azido, chloro, bromo or fluoro substitutents. R 2 is: lower alkyl or lower alkyl substituted with one or more chloro, bromo, fluoro, nitro, cyano, lower alkoxy or lower alkyl groups; R 3 is: perhalomethanesulfenyl or perhaloethanesulfenyl wherein the halogen substituents are chloro, bromo or fluoro; and R 4 is: hydrogen or lower alkyl; R 5 is: hydrogen or lower alkyl; and with the proviso that a cyano group is present in at least one of the groups R and R 2 .

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USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1980-06-13 1980-12-13 1981-06-14 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1984-06-13 1984-12-13 1985-06-14 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1988-06-13 1988-12-13 1989-06-14 $7700.00 Window Closed / Lapsed

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