US4051254A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Sulfonamido-and amidophenyl n-methylcarbamates and use as insecticides
Assignee: Bayer CropScience Inc USA
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Filing: 1975-12-19
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Granted: 1977-09-27
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Expires: 1995-12-19
Abstract
Abstract There are provided phenyl N-methylcarbamates substituted in the 4-position with groups, such as alkanesulfamido, haloalkanesulfamido, alkoxyalkanamido, haloalkanamido, alkylthioalkanamido, or furoylamido. These compounds are effective for the control of several insect species as systemic and stomach poison insecticides, as larvicides, and as ovicides.
Inventors
- 👤 Lester L. Maravetz
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 09:28
CPC Classifications
A; A01; A01N; A01N53/00; A01N47/00; A01N47/08; A01N47/10; A01N47/22; C; C07; C07D; C07D307/00; C07D307/02; C07D307/34; C07D307/56; C07D307/68
Claims Analysis
Total Claims: 42
Claim 1
Independent Claim
103 words
A compound having the structure: ##STR15## wherein R' is (C 1 -C 5 ) alkyl, Cl, or (C 1 -C 4 ) alkoxy; n is 1 to 3; R" is -SO 2 R'" wherein R'" is (C 1 -C 4 ) alkyl, (C 3 -C 6 ) cycloalkyl, (C 1 -C 4 ) monohaloalkyl, phenyl, or tolyl or R" is ##STR16## wherein R"" is (C 1 -C 4 ) alkoxy (C 1 -C 4 ) alkyl, (C 1 -C 4 ) haloalkyl, phenoxy (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylthio (C 1 -C 4 ) alkyl, and furyl.
Claim 2
Dependent Claim
103 words
A compound having the structure: ##STR15## wherein R' is (C 1 -C 5 ) alkyl, Cl, or (C 1 -C 4 ) alkoxy; n is 1 to 3; R" is -SO 2 R'" wherein R'" is (C 1 -C 4 ) alkyl, (C 3 -C 6 ) cycloalkyl, (C 1 -C 4 ) monohaloalkyl, phenyl, or tolyl or R" is ##STR16## wherein R"" is (C 1 -C 4 ) alkoxy (C 1 -C 4 ) alkyl, (C 1 -C 4 ) haloalkyl, phenoxy (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylthio (C 1 -C 4 ) alkyl, and furyl.
Claim 3
Dependent Claim
11 words
A compound of claim 1, wherein said compound is 3-methyl-4-(methoxyacetamido)phenyl N-methylcarbamate.
Claim 4
Dependent Claim
11 words
A compound of claim 1, wherein said compound is 3-methyl-4-(trichloroacetamido)phenyl N-methylcarbamate.
Claim 5
Dependent Claim
11 words
A compound of claim 1, wherein said compound is 3-methyl-4-(3-chloropropionamido)phenyl N-methylcarbamate.
Claim 6
Dependent Claim
11 words
A compound of claim 1, wherein said compounds is 3-methyl-4-(chlorodifluoroacetamido)phenyl N-methylcarbamate.
Claim 7
Dependent Claim
11 words
A compound of claim 1, wherein said compounds is 3,5-dimethyl-4-(ethanesulfonamido)phenyl N-methylcarbamate.
Claim 8
Dependent Claim
11 words
A compound of claim 1, wherein said compound is 3-methyl-4-(propoxyacetamido)phenyl N-methylcarbamate.
Claim 9
Dependent Claim
11 words
A compound of claim 1, wherein said compound is 3-methyl-4-(α-phenoxypropionamido)phenyl N-methylcarbamate.
Claim 10
Dependent Claim
11 words
A compound of claim 1, wherein said compound is 3-methyl-4-(dichloroacetamido)phenyl N-methylcarbamate.
Claim 11
Dependent Claim
11 words
A compound of claim 1, wherein said compound is 3-methyl-4-(trifluoroacetamido)phenyl N-methylcarbamate.
Claim 12
Dependent Claim
11 words
A compound of claim 1, wherein said compound is 3-methyl-4-(2-furoylamido)phenyl N-methylcarbamate.
Claim 13
Dependent Claim
11 words
A compound of claim 1, wherein said compound is 3,5-dimethyl-4-(ethoxyacetamido)phenyl N-methylcarbamate.
Claim 14
Dependent Claim
11 words
A compound of claim 1, wherein said compound is 3,5-dimethyl-4-(chloromethanesulfonamido)phenyl N-methylcarbamate.
Claim 15
Dependent Claim
124 words
An insecticidal composition comprising a carrier and between about 0.0001 percent and about 80 percent, by weight of said composition of a compound having the structure: ##STR17## wherein R' is (C 1 -C 5 ) alkyl, Cl, or (C 1 -C 4 ) alkoxy; n is 1 to 3; R" is --SO 2 R'", wherein R'" is (C 1 -C 4 ) alkyl, (C 3 -C 6 ) cycloalkyl, (C 1 -C 4 ) monohaloalkyl, phenyl, or tolyl or R" is ##STR18## wherein R"" is (C 1 -C 4 ) alkoxy (C 1 -C 4 ) alkyl, (C 1 -C 4 ) haloalkyl, phenoxy (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylthio (C 1 -C 4 ) alkyl, and furyl.
Claim 16
Dependent Claim
124 words
An insecticidal composition comprising a carrier and between about 0.0001 percent and about 80 percent, by weight of said composition of a compound having the structure: ##STR17## wherein R' is (C 1 -C 5 ) alkyl, Cl, or (C 1 -C 4 ) alkoxy; n is 1 to 3; R" is --SO 2 R'", wherein R'" is (C 1 -C 4 ) alkyl, (C 3 -C 6 ) cycloalkyl, (C 1 -C 4 ) monohaloalkyl, phenyl, or tolyl or R" is ##STR18## wherein R"" is (C 1 -C 4 ) alkoxy (C 1 -C 4 ) alkyl, (C 1 -C 4 ) haloalkyl, phenoxy (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylthio (C 1 -C 4 ) alkyl, and furyl.
Claim 17
Dependent Claim
11 words
A composition of claim 14, wherein said compound is 3-methyl-4-(methoxyacetamido)phenyl N-methylcarbamate.
Claim 18
Dependent Claim
11 words
A composition of claim 14, wherein said compound is 3-methyl-4-(trichloroacetamido)phenyl N-methylcarbamate.
Claim 19
Dependent Claim
11 words
A composition of claim 14, wherein said compound is 3-methyl-4-(3-chloropropionamido)phenyl N-methylcarbamate.
Claim 20
Dependent Claim
11 words
A composition of claim 14, wherein said compound is 3-methyl-4-(chlorofluoroacetamido)phenyl N-methylcarbamate.
Claim 21
Dependent Claim
11 words
A composition of claim 14, wherein said compound is 3,5-dimethyl-4-(ethanesulfonamido)phenyl N-methylcabamate.
Claim 22
Dependent Claim
11 words
A composition of claim 14, wherein said compound is 3-methyl-4-(propoxyacetamido)phenyl N-methylcarbamate.
Claim 23
Dependent Claim
11 words
A composition of claim 14, wherein said compound is 3-methyl-4-(α-phenoxypropionamido)phenyl N-methylcarbamate.
Claim 24
Dependent Claim
11 words
A composition of claim 14, wherein said compound is 3-methyl-4-(dichloroacetamido)phenyl N-methylcarbamate.
Claim 25
Dependent Claim
11 words
A composition of claim 14, wherein said compound is 3-methyl-4-(trifluoroacetamido)phenyl N-methylcarbamate.
Claim 26
Dependent Claim
11 words
A composition of claim 14, wherein said compound is 3-methyl-4-(2-furoylamido)phenyl N-methylcarbamate.
Claim 27
Dependent Claim
11 words
A composition of claim 14, wherein said compound is 3,5-dimethyl-4-(ethoxyacetamido)phenyl N-methylcarbamate.
Claim 28
Dependent Claim
11 words
A composition of claim 14, wherein said compound is 3,5-dimethyl-4-(chloromethanesulfonamido)phenyl N-methylcarbamate.
Claim 29
Independent Claim
123 words
The method for combatting insects which comprises contacting them, their larvae, or their ova with an insecticidally effective amount of a compound having the structure: ##STR19## wherein R' is (C 1 -C 5 ) alkyl, Cl, or (C 1 -C 4 ) alkoxy; n is 1 to 3; R" is -SO 2 R'", wherein R'" is (C 1 -C 4 ) alkyl, (C 3 -C 6 ) cycloalkyl, (C 1 -C 4 ) monohaloalkyl, phenyl, or tolyl or R" is ##STR20## wherein R"" is (C 1 -C 4 ) alkoxy (C 1 -C 4 ) alkyl, (C 1 -C 4 ) haloalkyl, phenoxy (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylthio (C 1 -C 4 ) alkyl, and furyl.
Claim 30
Independent Claim
123 words
The method for combatting insects which comprises contacting them, their larvae, or their ova with an insecticidally effective amount of a compound having the structure: ##STR19## wherein R' is (C 1 -C 5 ) alkyl, Cl, or (C 1 -C 4 ) alkoxy; n is 1 to 3; R" is -SO 2 R'", wherein R'" is (C 1 -C 4 ) alkyl, (C 3 -C 6 ) cycloalkyl, (C 1 -C 4 ) monohaloalkyl, phenyl, or tolyl or R" is ##STR20## wherein R"" is (C 1 -C 4 ) alkoxy (C 1 -C 4 ) alkyl, (C 1 -C 4 ) haloalkyl, phenoxy (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylthio (C 1 -C 4 ) alkyl, and furyl.
Claim 31
Dependent Claim
11 words
The method of claim 27, wherein said compound is 3-methyl-4-(methoxyacetamido)phenyl N-methylcarbamate.
Claim 32
Dependent Claim
11 words
The method of claim 27, wherein said compound is 3-methyl-4-(trichloroacetamido)phenyl N-methylcarbamate.
Claim 33
Dependent Claim
11 words
The method of claim 27, wherein said compound is 3-methyl-4-(3-chloropropionamido)phenyl N-methylcarbamate.
Claim 34
Dependent Claim
11 words
The method of claim 27, wherein said compound is 3-methyl-4-(chlorodifluoroacetamido)phenyl N-methylcarbamate.
Claim 35
Dependent Claim
11 words
The method of claim 27, wherein said compound is 3,5-dimethyl-4-(ethanesulfonamido)phenyl N-methylcarbamate.
Claim 36
Dependent Claim
11 words
The method of claim 27, wherein said compound is 3-methyl-4-(propoxyacetamido)phenyl N-methylcarbamate.
Claim 37
Dependent Claim
11 words
The method of claim 27, wherein said compound is 3-methyl-4-(α-phenoxypropionamido)phenyl N-methylcarbamate.
Claim 38
Dependent Claim
11 words
The method of claim 27, wherein said compound is 3-methyl-4-(dichloroacetamido)phenyl N-methylcarbamate.
Claim 39
Dependent Claim
11 words
The method of claim 27, wherein said compound is 3-methyl-4-(trifluoroacetamido)phenyl N-methylcarbamate.
Claim 40
Dependent Claim
11 words
The method of claim 27, wherein said compound is 3-methyl-4-(2-furoylamido)phenyl N-methylcarbamate.
Claim 41
Dependent Claim
11 words
The method of claim 27, wherein said compound is 3,5-dimethyl-4-(ethoxyacetamido)phenyl N-methylcarbamate.
Claim 42
Dependent Claim
11 words
The method of claim 27, wherein said compound is 3,5-dimethyl-4-(chloromethanesulfonamido)phenyl N-methylcarbamate.
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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) | 1980-09-26 | 1981-03-28 | 1981-09-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-09-26 | 1985-03-28 | 1985-09-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-09-26 | 1989-03-28 | 1989-09-27 | $7700.00 | Window Closed / Lapsed |