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US4771066A
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4-haloalkylthio-5-amino-1-arylpyrazoles, composition containing them, and insecticidal and acaricidal method of using them
Assignee: Bayer AG
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Filing: 1987-02-12
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Granted: 1988-09-13
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Expires: 2007-02-12
Abstract
Abstract Insecticidally and acarididally active 1-arylpyrazoles of the formula ##STR1## in which R 1 represents hydrogen, alkyl or halogen alkyl, R 2 represents alkyl, alkenyl, alkinyl, cycloalkyl, halogenoalkyl, halogenoalkenyl, alkoxyalkyl, alkylthioalkyl, alkylsulphinylalkyl, alkylsulphonylalkyl, optionally substituted aralkyl or optionally substituted aryl, R 3 represents alkyl, alkenyl, alkinyl, halogenoalkyl, halogenoalkenyl, alkoxyalkyl, alkylthioalkyl, cycloalkyl or optionally substituted aralkyl, R 4 represents alkyl, alkenyl, alkinyl, halogenoalkyl, halogenoalkenyl, alkoxyalkyl, alkylthioalkyl, cycloalkyl or optionally substituted aralkyl, and, in addition, also represents hydrogen in the case where R 3 does not simultaneously represent unsubstituted alkyl, or R 3 and R 4 , together with the nitrogen atom to which they are bound, represent a saturated heterocycle, which can optionally contain further heteroatoms, Ar represents in each case optionally substituted phenyl or pyridyl, and n represents a number 0, 1 or 2.
Inventors
- 👤 Reinhold Gehring
- 👤 Uta Jensen-Korte
- 👤 Otto Schallner
- 👤 Jorg Stetter
- 👤 Heinz-Jurgen Wroblowsky
- 👤 Benedikt Becker
- 👤 Wolfgang Behrenz
- 👤 Bernhard Homeyer
- 👤 Wilhelm Stendel
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 17:36
CPC Classifications
C; C07; C07D; C07D231/00; C07D231/02; C07D231/10; C07D231/14; C07D231/18; C07D401/00; C07D401/02; C07D401/04; A; A01; A01N; A01N43/00; A01N43/48; A01N43/56; A01N47/00; A01N47/02; A61; A61P; A61P33/00; C07D231/44
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
100 words
A 1-aryl-pyrazole of the formula ##STR118## in which R 1 represents hydrogen, or alkyl or halogenoalkyl having 1 to 4 carbon atoms, R 2 represents straight-chain or branched halogenoalkyl having up to 8 carbon atoms and up to 17 identical or different halogen atoms, ##STR119## pyrrolidinyl, piperidinyl, perhydroazepinyl or morpholinyl, Ar represents phenyl mono- or poly-substituted by identical or different residues selected from CN, NO 2 , halogen C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxycarbonyl, halogeno-C 1 -C 4 -alkyl, halogeno-C 1 -C 4 -alkoxy, and n represents 0, 1 or 2.
Claim 2
Dependent Claim
100 words
A 1-aryl-pyrazole of the formula ##STR118## in which R 1 represents hydrogen, or alkyl or halogenoalkyl having 1 to 4 carbon atoms, R 2 represents straight-chain or branched halogenoalkyl having up to 8 carbon atoms and up to 17 identical or different halogen atoms, ##STR119## pyrrolidinyl, piperidinyl, perhydroazepinyl or morpholinyl, Ar represents phenyl mono- or poly-substituted by identical or different residues selected from CN, NO 2 , halogen C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxycarbonyl, halogeno-C 1 -C 4 -alkyl, halogeno-C 1 -C 4 -alkoxy, and n represents 0, 1 or 2.
Claim 3
Dependent Claim
142 words
A 1-aryl-pyrazole according to claim 1, in which R 1 represents hydrogen, methyl, ethyl, n- or ipropyl or trifluoromethyl, R 2 represents chloromethyl, difluoromethyl, difluorochloromethyl, fluorodichloromethyl, trifluoromethyl, pentafluoroethyl, pentachloroethyl, fluorotetrachloroethyl, difluorotrichloroethyl, trifluorodichloroethyl, tetrafluorochloroethyl, heptapfluoropropyl, chloroethyl, bromoethyl, chloropropyl, bromopropyl, dichloromethyl, chlorofluoromethyl, trichloromethyl, trifluoroethyl, trifluorochloroethyl, tetrafluoroethyl, difluorochloroethyl, fluorodibromomethyl, difluorobromomethyl, or fluorochlorobromomethyl, R 3 and R 4 , together with the nitrogen atom to which they are bound, represent pyrrolidinyl, piperidinyl, perhydroazepinyl or moropholinyl, and Ar represents optionally mono- to pentasubstituted phenyl, the substituents being identical or different and being selected rom the group consisting of cyano, nitro, fluorine, chlorine, bromine, iodine, methyl, ethyl, n- and i-propyl, n-, i-, s- and t-bytyl, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, trifluoromethyl, trichloromethyl, dichlorofluoromethyl, difluorochloromethyl, chloromethyl, dichloromethyl, difluoromethyl, pentafluoroethyl, tetrafluoroethyl, trifluorochloroethyl, trifluoroethyl, difluorodichloroethyl, trifluorodichloroethyl, pentachloroethyl, trifluoromethoxy, trichloromethoxy, dichlorofluoromethoxy, difluorochloromethoxy, chloromethoxy, dichloromethoxy, difluoromethyoxy, pentafluoroethoxy, tetrafluoroethoxy, trifluorochlroethoxy, trifluoroethoxy, difluorodichloroethoxy, trifluorodichloroethoxy, or pentachloroethoxy.
Claim 4
Dependent Claim
15 words
A compound according to claim 1, wherein such compound is 4-dichlorofluoromethane-sulphonyl-5-(2-methoxyethyl)-amino-1-(2,6-dichloro-4-trifluoromethyl-phenyl)-pyrazole of the formula ##STR120##
Claim 5
Dependent Claim
15 words
A compound according to claim 1, wherein such compound is 4-dichlorofluoromethanesulphenyl-5-dimethylamino-1-(2,6-dichloro-4-trifluoromethyl-phenyl)-pyrazole of the formula ##STR121##
Claim 6
Dependent Claim
15 words
A compound according to claim 1 wherein such compound is 4-dichlorofluoromethanesulphonyl-5-dimethylamino-1-(2,6-dichloro-4-trifluoromethyl-phenyl)-pyrazole of the formula ##STR122##
Claim 7
Dependent Claim
15 words
A compound according to claim 1 wherein such compound is 5-dimethylamino-3-methyl-4-trifluoromethylthio-1-(2,6-dichloro-4-trifluoromethoxy-phenyl)-pyrazole of the formula ##STR123##
Claim 8
Dependent Claim
15 words
A compound according to claim 1 wherein such compound is 4-chlorodifluoromethylthio-5-dimethylamino-3-methyl-1-(2,6-dichloro-4-trifluoromethyl-phenyl)-pyrazole of the formula ##STR124##
Claim 9
Dependent Claim
16 words
A compound according to claim 1 wherein such compound is 4-dichlorofluoromethylthio-5-diethylamino-1-(2,6-dichloro 4-trifluoromethyl-phenyl)-pyrazole of the formula ##STR125##
Claim 10
Dependent Claim
15 words
A compund according to claim 1 wherein such compound is 4-dichlorofluoromethylthio-5-(N-methyl-N-ethyl-amino)-1-(2,6-dichloro-4-trifluoromethyl-phenyl)-pyrazole of the formula ##STR126##
Claim 11
Dependent Claim
24 words
An insecticidal or acaricidal composition comprising an insecticidally or acaricidally effective amount of a compound according to claim 1 in admixture with a diluent.
Claim 12
Dependent Claim
38 words
A method of combating insects or acarids which comprises applying to such insects or acarids or to a habitat thereof an insecticidally or acarididally effective amount of a compound according to claim 1 in admixture with a diluent.
Claim 13
Dependent Claim
18 words
The method according to claim 11, wherein such compound 4-dichlorofluoromethane-sulphonyl-5-(2-methoxyethyl)-amino-1-(2,6-dichloro-4-trifluoromethyl-phenyl)-pyrazole, 4-dichlorofluoromethanesulphenyl-5-dimethylamino-1-(2,6-dichloro-4-trifluoromethyl-phenyl)-pyrazole, 4-dichlorofluoromethanesulphonyl-5-dimethylamino-1- (2,6-dichloro-4-trifluoromethyl-phenyl)-pyrazole, 5-dimethylamino-3-methyl-4-trifluoromethylthio-1(2,6-dichloro-4-trifluoromethoxy-phenyl)-pyrazole, 4-chlorodifluoromethylthio-5-dimethylamino-3-methyl-1-(2,6-dichloro-4-trifluoromethyl-phenyl)-pyrazole, 4-dichlorofluoromethylthio-5-diethylamino-1-(2,6-dichloro-4-trifluoromethyl-phenyl)-pyrazole or 4-dichlorofluoromethylthio-5-(N-methyl-N-ethyl-amino)-1-(2,6-dichloro-4-trifluoromethyl-phenyl)-pyrazole.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1991-09-13 | 1992-03-14 | 1992-09-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-09-13 | 1996-03-14 | 1996-09-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-09-13 | 2000-03-14 | 2000-09-13 | $7700.00 | Window Closed / Lapsed |