US3996366A
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Thio derivatives of imidazol-1-yl carboxamides
Assignee: Boots Co PLC
•
Filing: 1974-11-14
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Granted: 1976-12-07
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Expires: 1994-11-14
Abstract
Abstract Novel imidazole compounds, pesticidal compositions and methods of using them, and their preparation are described. The compounds have the formula <IMAGE> in which X is oxygen or sulphur, R3 is hydrogen, alkyl, alkenyl or optionally substituted alkylthio, alkenylthio, aralkylthio, alkoxyalkyl or alkylthioalkyl, R4 is alkyl or cycloalkyl, and R1 and R2 are each lower alkyl or alkenyl, R1 is lower alkyl and R2 is alkoxyalkyl or haloalkyl, or R1 and R2 together with the nitrogen atom to which they are attached, form an optionally substituted heterocyclic ring; and salts thereof. Novel compounds are of particular value against insects e.g. aphids, and against other pests, e.g. acarids.
Inventors
- 👤 Maurice W. Baker
- 👤 John C. Kerry
- 👤 Antonin Kozlik
- 👤 John R. Marshall
- 👤 Kenneth J. Nichol
- 👤 David M. Weighton
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 11:40
CPC Classifications
C; C07; C07D; C07D209/00; C07D209/02; C07D209/44; C07D209/48; C07D233/00; C07D233/54; C07D233/66; C07D233/84
Claims Analysis
Total Claims: 27
Claim 1
Independent Claim
228 words
A compound of the formula ##STR8## in which X is selected from the group consisting of oxygen and sulphur, R 3 is selected from the group consisting of alkylthio of 1 to 6 carbon atoms optionally substituted with at least one substituent selected from the group consisting of chloro, bromo, fluoro, methoxy, ethoxy, methoxy carbonyl, ethoxy carbonyl, methylthio, ethylthio, vinyloxy, dimethylamino and diethylamino, alkenylthio of 2 to 6 carbon atoms optionally substituted with one to two halo substituents selected from the group consisting of bromo, fluoro and chloro, aralkylthio of 7 to 8 carbon atoms optionally substituted with one or more substituents selected from the group consisting of methyl, nitro, methoxy, trifluoromethyl and chloro; R 4 is selected from the group consisting of alkyl of 1 to 10 carbon atoms and cycloalkyl of 3 to 7 carbon atoms optionally substituted with 1 to 3 methyl groups; and R 1 and R 2 are selected from the group consisting of (a) lower alkyl and lower alkenyl, and (b) R 1 is lower alkyl and R 2 is selected from the group consisting of alkoxy alkyl of 3 to 6 carbon atoms and lower halo alkyl; and salts thereof of acids selected from the group consisting of hydrochloric, hydrobromic, hydroiodic, hydrofluoric, sulphuric, nitric, phosphoric, perchloric, sulphamic, formic, acetic, trichloroacetic, oxalic, picric, benzenesulphonic, dodecylbenzenesulphonic, p-toluenesulphonic, stearic, flavianic, embonic or tetraiodophthalaic acids.
Claim 2
Dependent Claim
228 words
A compound of the formula ##STR8## in which X is selected from the group consisting of oxygen and sulphur, R 3 is selected from the group consisting of alkylthio of 1 to 6 carbon atoms optionally substituted with at least one substituent selected from the group consisting of chloro, bromo, fluoro, methoxy, ethoxy, methoxy carbonyl, ethoxy carbonyl, methylthio, ethylthio, vinyloxy, dimethylamino and diethylamino, alkenylthio of 2 to 6 carbon atoms optionally substituted with one to two halo substituents selected from the group consisting of bromo, fluoro and chloro, aralkylthio of 7 to 8 carbon atoms optionally substituted with one or more substituents selected from the group consisting of methyl, nitro, methoxy, trifluoromethyl and chloro; R 4 is selected from the group consisting of alkyl of 1 to 10 carbon atoms and cycloalkyl of 3 to 7 carbon atoms optionally substituted with 1 to 3 methyl groups; and R 1 and R 2 are selected from the group consisting of (a) lower alkyl and lower alkenyl, and (b) R 1 is lower alkyl and R 2 is selected from the group consisting of alkoxy alkyl of 3 to 6 carbon atoms and lower halo alkyl; and salts thereof of acids selected from the group consisting of hydrochloric, hydrobromic, hydroiodic, hydrofluoric, sulphuric, nitric, phosphoric, perchloric, sulphamic, formic, acetic, trichloroacetic, oxalic, picric, benzenesulphonic, dodecylbenzenesulphonic, p-toluenesulphonic, stearic, flavianic, embonic or tetraiodophthalaic acids.
Claim 3
Dependent Claim
142 words
A compound according to claim 1 in which X is selected from the group consisting of oxygen and sulphur, R 3 is selected from the group consisting of alkylthio of 1 to 6 carbon atoms, and aralkylthio of 7 to 8 carbon atoms optionally substituted with one or more substituents selected from the group consisting of methyl, nitro, methoxy, trifluoromethyl and chloro; R 4 is selected from the group consisting of alkyl of 1 to 10 carbon atoms and cycloalkyl of 3 to 7 carbon atoms optionally substituted with 1 to 3 methyl groups; and R 1 and R 2 are selected from the group consisting of (a) lower alkyl and lower alkenyl, and (b) R 1 is lower alkyl and R 2 is selected from the group consisting of alkoxy alkyl of 3 to 6 carbon atoms and lower halo alkyl.
Claim 4
Dependent Claim
11 words
A compound according to claim 2 in which X is oxygen.
Claim 5
Dependent Claim
23 words
A compound according to claim 3 in which R 1 is methyl and R 2 is alkyl of 1 to 4 carbon atoms.
Claim 6
Dependent Claim
18 words
A compound according to claim 4 in which R 3 is alkylthio of 1 to 4 carbon atoms.
Claim 7
Dependent Claim
27 words
A compound according to claim 5 in which R 4 is selected from the group consisting of tert. butyl, sec. butyl, propyl, 1-ethylpropyl, isopropyl and tert. pentyl.
Claim 8
Dependent Claim
1 words
1-dimethylcarbamoyl-2-methylthio-4(5)-tert.butylimidazole.
Claim 9
Dependent Claim
1 words
1-dimethylcarbamoyl-2-methylthio-4(5)-tert.butylimidazole.
Claim 10
Dependent Claim
243 words
An insecticidal composition which comprises an insecticidally effective amount of a compound of the formula ##STR9## in which X is selected from the group consisting of oxygen and sulphur, R 3 is selected from the group consisting of alkylthio of 1 to 6 carbon atoms optionally substituted with at least one substituent selected from the group consisting of chloro, bromo, fluoro, methoxy, ethoxy, methoxy carbonyl, ethoxy carbonyl, methylthio, ethylthio, vinyloxy, dimethylamino and diethylamino, alkenylthio of 2 to 6 carbon atoms optionally substituted with one to two halo substituents selected from the group consisting of bromo, fluoro and chloro, aralkylthio of 7 to 8 carbon atoms optionally substituted with one or more substituents selected from the group consisting of methyl, nitro, methoxy, trifluoromethyl and chloro; R 4 is selected from the group consisting of alkyl of 1 to 10 carbon atoms and cycloalkyl of 3 to 7 carbon atoms optionally substituted with 1 to 3 methyl groups; and R 1 and R 2 are selected from the group consisting of (a) lower alkyl and lower alkenyl, and (b) R 1 is lower alkyl and R 2 is selected from the group consisting of alkoxy alkyl of 3 to 6 carbon atoms and lower halo alkyl; and salts thereof of acids selected from the group consisting of hydrochloric, hydrobromic, hydroiodic, hydrofluoric, sulphuric, nitric, phosphoric, perchloric, sulphamic, formic, acetic, trichloroacetic, oxalic, picric, benzenesulphonic, dodecylbenzenesulphonic, p-toluenesulphonic, stearic, flavianic, embonic or tetraiodophthalaic acids; together with a suitable carrier.
Claim 11
Dependent Claim
243 words
An insecticidal composition which comprises an insecticidally effective amount of a compound of the formula ##STR9## in which X is selected from the group consisting of oxygen and sulphur, R 3 is selected from the group consisting of alkylthio of 1 to 6 carbon atoms optionally substituted with at least one substituent selected from the group consisting of chloro, bromo, fluoro, methoxy, ethoxy, methoxy carbonyl, ethoxy carbonyl, methylthio, ethylthio, vinyloxy, dimethylamino and diethylamino, alkenylthio of 2 to 6 carbon atoms optionally substituted with one to two halo substituents selected from the group consisting of bromo, fluoro and chloro, aralkylthio of 7 to 8 carbon atoms optionally substituted with one or more substituents selected from the group consisting of methyl, nitro, methoxy, trifluoromethyl and chloro; R 4 is selected from the group consisting of alkyl of 1 to 10 carbon atoms and cycloalkyl of 3 to 7 carbon atoms optionally substituted with 1 to 3 methyl groups; and R 1 and R 2 are selected from the group consisting of (a) lower alkyl and lower alkenyl, and (b) R 1 is lower alkyl and R 2 is selected from the group consisting of alkoxy alkyl of 3 to 6 carbon atoms and lower halo alkyl; and salts thereof of acids selected from the group consisting of hydrochloric, hydrobromic, hydroiodic, hydrofluoric, sulphuric, nitric, phosphoric, perchloric, sulphamic, formic, acetic, trichloroacetic, oxalic, picric, benzenesulphonic, dodecylbenzenesulphonic, p-toluenesulphonic, stearic, flavianic, embonic or tetraiodophthalaic acids; together with a suitable carrier.
Claim 12
Dependent Claim
143 words
An insecticidal composition according to claim 8 in which X is selected from the group consisting of oxygen and sulphur, R 3 is selected from the group consisting of alkylthio of 1 to 6 carbon atoms, and aralkylthio of 7 to 8 carbon atoms optionally substituted with one or more substituents selected from the group consisting of methyl, nitro, methoxy, trifluoromethyl and chloro; R 4 is selected from the group consisting of alkyl of 1 to 10 carbon atoms and cycloalkyl of 3 to 7 carbon atoms optionally substituted with 1 to 3 methyl groups; and R 1 and R 2 are selected from the group consisting of (a) lower alkyl and lower alkenyl, and (b) R 1 is lower alkyl and R 2 is selected from the group consisting of alkoxy alkyl of 3 to 6 carbon atoms and lower halo alkyl.
Claim 13
Dependent Claim
12 words
An insecticidal composition according to claim 9 in which X is oxygen.
Claim 14
Dependent Claim
24 words
An insecticidal composition according to claim 10 in which R 1 is methyl and R 2 is alkyl of 1 to 4 carbon atoms.
Claim 15
Dependent Claim
19 words
An insecticidal composition according to claim 11 in which R 3 is alkylthio of 1 to 4 carbon atoms.
Claim 16
Dependent Claim
28 words
An insecticidal composition according to claim 12 in which R 4 is selected from the group consisting of tert. butyl, sec. butyl, propyl, 1-ethylpropyl, isopropyl and tert. pentyl.
Claim 17
Dependent Claim
16 words
An insecticidal composition which comprises an insecticidally effective amount of 1-dimethylcarbamoyl-2-methylthio-4(5)-tert.butylimidazole, together with a suitable carrier.
Claim 18
Dependent Claim
16 words
An insecticidal composition which comprises an insecticidally effective amount of 1-dimethylcarbamoyl-2-methylthio-4(5)-tert.butylimidazole, together with a suitable carrier.
Claim 19
Independent Claim
248 words
A method of combatting insects which comprises applying to said insects of the locus thereof an insecticidally effective amount of a compound of the formula ##STR10## in which X is selected from the group consisting of oxygen and sulphur, R 3 is selected from the group consisting of alkylthio of 1 to 6 carbon atoms optionally substituted with at least one substituent selected from the group consisting of chloro, bromo, fluoro, methoxy, ethoxy, methoxy carbonyl, ethoxy carbonyl, methylthio, ethylthio, vinyloxy, dimethylamino and diethylamino, alkenylthio of 2 to 6 carbon atoms optionally substituted with one to two halo substituents selected from the group consisting of bromo, fluoro and chloro, aralkylthio of 7 to 8 carbon atoms optionally substituted with one or more substituents selected from the group consisting of methyl, nitro, methoxy, trifluoromethyl and chloro; R 4 is selected from the group consisting of alkyl of 1 to 10 carbon atoms and cycloalkyl of 3 to 7 carbon atoms optionally substituted with 1 to 3 methyl groups; and R 1 and R 2 are selected from the group consisting of (a) lower alkyl and lower alkenyl, and (b) R 1 is lower alkyl and R 2 is selected from the group consisting of alkoxy alkyl of 3 to 6 carbon atoms and lower halo alkyl; and salts thereof of acids selected from the group consisting of hydrochloric, hydrobromic, hydroiodic, hydrofluoric, sulphuric, nitric, phosphoric, perchloric, sulphamic, formic, acetic, trichloroacetic, oxalic, picric, benzenesulphonic, dodecylbenzenesulphonic, p-toluenesulphonic, stearic, flavianic, embonic or tetraiodophthalaic acids.
Claim 20
Independent Claim
248 words
A method of combatting insects which comprises applying to said insects of the locus thereof an insecticidally effective amount of a compound of the formula ##STR10## in which X is selected from the group consisting of oxygen and sulphur, R 3 is selected from the group consisting of alkylthio of 1 to 6 carbon atoms optionally substituted with at least one substituent selected from the group consisting of chloro, bromo, fluoro, methoxy, ethoxy, methoxy carbonyl, ethoxy carbonyl, methylthio, ethylthio, vinyloxy, dimethylamino and diethylamino, alkenylthio of 2 to 6 carbon atoms optionally substituted with one to two halo substituents selected from the group consisting of bromo, fluoro and chloro, aralkylthio of 7 to 8 carbon atoms optionally substituted with one or more substituents selected from the group consisting of methyl, nitro, methoxy, trifluoromethyl and chloro; R 4 is selected from the group consisting of alkyl of 1 to 10 carbon atoms and cycloalkyl of 3 to 7 carbon atoms optionally substituted with 1 to 3 methyl groups; and R 1 and R 2 are selected from the group consisting of (a) lower alkyl and lower alkenyl, and (b) R 1 is lower alkyl and R 2 is selected from the group consisting of alkoxy alkyl of 3 to 6 carbon atoms and lower halo alkyl; and salts thereof of acids selected from the group consisting of hydrochloric, hydrobromic, hydroiodic, hydrofluoric, sulphuric, nitric, phosphoric, perchloric, sulphamic, formic, acetic, trichloroacetic, oxalic, picric, benzenesulphonic, dodecylbenzenesulphonic, p-toluenesulphonic, stearic, flavianic, embonic or tetraiodophthalaic acids.
Claim 21
Dependent Claim
145 words
A method of combatting insects according to claim 15 in which X is selected from the group consisting of oxygen and sulphur, R 3 is selected from the group consisting of alkylthio of 1 to 6 carbon atoms, and aralkylthio of 7 to 8 carbon atoms optionally substituted with one or more substituents selected from the group consisting of methyl, nitro, methoxy, trifluoromethyl and chloro; R 4 is selected from the group consisting of alkyl of 1 to 10 carbon atoms and cycloalkyl of 3 to 7 carbon atoms optionally substituted with 1 to 3 methyl groups; and R 1 and R 2 are selected from the group consisting of (a) lower alkyl and lower alkenyl, and (b) R 1 is lower alkyl and R 2 is selected from the group consisting of alkoxy alkyl of 3 to 6 carbon atoms and lower halo alkyl.
Claim 22
Dependent Claim
14 words
A method of combatting insects according to claim 16 in which X is oxygen.
Claim 23
Dependent Claim
26 words
A method of combatting insects according to claim 17 in which R 1 is methyl and R 2 is alkyl of 1 to 4 carbon atoms.
Claim 24
Dependent Claim
21 words
A method of combatting insects according to claim 18 in which R 3 is alkylthio of 1 to 4 carbon atoms.
Claim 25
Dependent Claim
30 words
A method of combatting insects according to claim 19 in which R 4 is selected from the group consisting of tert. butyl, sec. butyl, propyl, 1-ethylpropyl, isopropyl and tert. pentyl.
Claim 26
Independent Claim
21 words
A method of combatting insects which comprises applying to said insects or the locus thereof an insecticidally effective amount of 1-dimethylcarbamoyl-2-methylthio-4(5)-tert.butylimidazole.
Claim 27
Independent Claim
21 words
A method of combatting insects which comprises applying to said insects or the locus thereof an insecticidally effective amount of 1-dimethylcarbamoyl-2-methylthio-4(5)-tert.butylimidazole.
References Cited (Backward Citations)
US3248398A
Cited
US3651080A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-12-07 | 1980-06-07 | 1980-12-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-12-07 | 1984-06-07 | 1984-12-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-12-07 | 1988-06-07 | 1988-12-07 | $7700.00 | Window Closed / Lapsed |