Patent US3615225A successfully refreshed from Google Patents.
Patent US4791124A successfully refreshed from Google Patents.
US4791124A
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Photoactive azole pesticides
Assignee: FMC Corp
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Filing: 1987-04-02
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Granted: 1988-12-13
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Expires: 2007-04-02
Abstract
Abstract Oxazole and thiazole compounds of the following formula are photodynamic insecticides and acaricides as well as nematicides: ##STR1## wherein W is selected from O and S; R 2 is selected from optionally substituted thienyl and optionally substituted phenyl; R 4 is selected from hydrogen, lower alkyl, lower haloalkyl, thienyl, tri(lower alkyl)silyl, and optionally substituted phenyl; R 5 is selected from optionally substituted thienyl and optionally substituted phenyl; at least one of R 2 and R 5 is an optionally substituted thienyl group, and R 4 is other than hydrogen when R 4 and R 5 are each unsubstituted phenyl or thienyl.
Inventors
- 👤 Kathryn A. Lutomski
- 👤 Susan E. Burkart
- 👤 Richard B. Phillips
- 👤 David M. Roush
- 👤 Ignatius J. Turchi
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 23:23
CPC Classifications
C; C07; C07D; C07D413/00; C07D413/02; C07D413/04; A; A01; A01N; A01N43/00; A01N43/72; A01N43/74; A01N55/00; C07D417/00; C07D417/02; C07D417/04; C07D417/14
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
197 words
A compound of the formula ##STR3## wherein W is selected from O and S; R 2 is selected from the group consisting of phenyl, naphthyl, 2,2-difluoro-1,3-benzodioxyl, phenyl substituted with at least one substituent selected from halogen, lower alkyl, lower haloalkyl, cyano, lower alkoxy, lower haloalkoxy, di(lower)alkylamino, phenylthiocarbonyl, or phenylsulfonyloxy, thienyl, and thienyl substituted with a substituent selected from halogen, lower alkyl, or thienyl; R 4 is selected from the group consisting of hydrogen, tri(lower)alkylsilyl, phenyl, halophenyl and thienyl; R 5 is selected from the group consisting of hydrogen, phenyl, phenyl substituted with at least one substituent selected from halogen, lower alkyl, lower haloalkyl, lower alkoxy, phenyl, or nitro, thienyl, and thienyl substituted with a substituent selected from lower alkyl, halogen, lower hydroxyalkyl, methylthio, lower haloalkylthio, lower alkylsulfonyl, lower haloalkenylthio, lower alkoxycarbonyl, and tri(lower)alkylsilyl; wherein at least one of R 2 and R 5 is an optionally substituted thienyl group and at least one of R 4 and R 5 is other than hydrogen, with the proviso: when R 4 is hydrogen, phenyl, or thienyl, then R 5 is other than hydrogen, phenyl, thienyl, alkylphenyl, or alkylthienyl; or R 2 is other than phenyl, alkylphenyl, thienyl or alkylthienyl.
Claim 2
Dependent Claim
197 words
A compound of the formula ##STR3## wherein W is selected from O and S; R 2 is selected from the group consisting of phenyl, naphthyl, 2,2-difluoro-1,3-benzodioxyl, phenyl substituted with at least one substituent selected from halogen, lower alkyl, lower haloalkyl, cyano, lower alkoxy, lower haloalkoxy, di(lower)alkylamino, phenylthiocarbonyl, or phenylsulfonyloxy, thienyl, and thienyl substituted with a substituent selected from halogen, lower alkyl, or thienyl; R 4 is selected from the group consisting of hydrogen, tri(lower)alkylsilyl, phenyl, halophenyl and thienyl; R 5 is selected from the group consisting of hydrogen, phenyl, phenyl substituted with at least one substituent selected from halogen, lower alkyl, lower haloalkyl, lower alkoxy, phenyl, or nitro, thienyl, and thienyl substituted with a substituent selected from lower alkyl, halogen, lower hydroxyalkyl, methylthio, lower haloalkylthio, lower alkylsulfonyl, lower haloalkenylthio, lower alkoxycarbonyl, and tri(lower)alkylsilyl; wherein at least one of R 2 and R 5 is an optionally substituted thienyl group and at least one of R 4 and R 5 is other than hydrogen, with the proviso: when R 4 is hydrogen, phenyl, or thienyl, then R 5 is other than hydrogen, phenyl, thienyl, alkylphenyl, or alkylthienyl; or R 2 is other than phenyl, alkylphenyl, thienyl or alkylthienyl.
Claim 3
Dependent Claim
22 words
The compound of claim 1 selected from the group consisting of 5-(5-methylthien-2-yl)-2-(4-trifluoromethylphenyl)thiazole; 5-(5-methylthien-2-yl)-2-((3,5-bis(trifluoromethyl)phenyl))thiazole; 2-(4-fluorophenyl)-5-(thien-2-yl)thiazole; 2-(4-trifluoromethylphenyl)-5-(thien-2-yl)thiazole; 2-(4-chlorophenyl)-5-(thien-2-yl)thiazole; 2-(4-trifluoromethylphenyl)-5-(thien-2-yl)thiazole; 5-(5-chlorothien-2-yl)-2-(4-fluorophenyl)thiazole; 2,5-bis(5-chlorothien-2-yl)thiazole; 2-(5-chlorothien-2-yl)-5-(5-methylthien-2-yl)thiazole; and 2-(2,2-difluoro-1,3-benzodioxol-5-yl)-5-(5-methylthien-2-yl)thiazole.
Claim 4
Dependent Claim
10 words
A compound of claim 1 wherein R 4 is hydrogen.
Claim 5
Dependent Claim
11 words
A compound of claim 3 wherein R 5 is substituted thienyl.
Claim 6
Dependent Claim
6 words
The compound of claim 4, 5-(5-methylthien-2-yl)-2-(4-trifluoromethylphenyl)thiazole.
Claim 7
Dependent Claim
6 words
The compound of claim 4, 5-(5-methylthien-2-yl)-2-[3,5-bis(tribromomethyl)phenyl]thiazole.
Claim 8
Dependent Claim
223 words
An insecticidal, acaricidal, or nematicidal composition comprising in admixture with an agriculturally acceptable carrier an insecticidally, acaricidally, or nematicidally effective amount of at least one compound of the formula ##STR4## wherein W is selected from O and S; R 2 is selected from the group consisting of phenyl, naphthyl, 2,2-difluoro-1,3-benzodioxyl, phenyl substituted with at least one substituent selected from halogen, lower alkyl, lower haloalkyl, cyano, lower alkoxy, lower haloalkoxy, di(lower)alkylamino, phenylthiocarbonyl, or phenylsulfonyloxy, thienyl, and thienyl substituted with a substituent selected from halogen, lower alkyl, or thienyl; R 4 is selected from the group consisting of hydrogen, tri(lower)alkylsilyl, phenyl, halophenyl and thienyl; R 5 is selected from the group consisting of hydrogen, lower alkyl, phenyl, phenyl substituted with at least one substituent selected from halogen, lower alkyl, lower haloalkyl, lower alkoxy, phenyl, or nitro, thienyl, and thienyl substituted with a substituent selected from lower alkyl, halogen, lower hydroxyalkyl, methylthio, lower haloalkylthio, lower alkylsulfonyl, lower haloalkenylthio, lower alkoxycarbonyl, and tri(lower)alkylsilyl; wherein at least one of R 2 and R 5 is an optionally substituted thienyl group and at least one of R 4 and R 5 is other than hydrogen, with the proviso: when R 4 is hydrogen, phenyl or thienyl, then R 5 is other than hydrogen, phenyl, thienyl, alkylphenyl, or alkylthienyl; or R 2 is other than phenyl, alkylphenyl, thienyl or alkylthienyl.
Claim 9
Dependent Claim
223 words
An insecticidal, acaricidal, or nematicidal composition comprising in admixture with an agriculturally acceptable carrier an insecticidally, acaricidally, or nematicidally effective amount of at least one compound of the formula ##STR4## wherein W is selected from O and S; R 2 is selected from the group consisting of phenyl, naphthyl, 2,2-difluoro-1,3-benzodioxyl, phenyl substituted with at least one substituent selected from halogen, lower alkyl, lower haloalkyl, cyano, lower alkoxy, lower haloalkoxy, di(lower)alkylamino, phenylthiocarbonyl, or phenylsulfonyloxy, thienyl, and thienyl substituted with a substituent selected from halogen, lower alkyl, or thienyl; R 4 is selected from the group consisting of hydrogen, tri(lower)alkylsilyl, phenyl, halophenyl and thienyl; R 5 is selected from the group consisting of hydrogen, lower alkyl, phenyl, phenyl substituted with at least one substituent selected from halogen, lower alkyl, lower haloalkyl, lower alkoxy, phenyl, or nitro, thienyl, and thienyl substituted with a substituent selected from lower alkyl, halogen, lower hydroxyalkyl, methylthio, lower haloalkylthio, lower alkylsulfonyl, lower haloalkenylthio, lower alkoxycarbonyl, and tri(lower)alkylsilyl; wherein at least one of R 2 and R 5 is an optionally substituted thienyl group and at least one of R 4 and R 5 is other than hydrogen, with the proviso: when R 4 is hydrogen, phenyl or thienyl, then R 5 is other than hydrogen, phenyl, thienyl, alkylphenyl, or alkylthienyl; or R 2 is other than phenyl, alkylphenyl, thienyl or alkylthienyl.
Claim 10
Dependent Claim
21 words
The composition of claim 7 selected from the group consisting of 5-(5-methylthien-2-yl)-2-(4-trifluoromethylphenyl)thiazole; 5-(5-methylthien-2-yl)-2-((3,5-bis(trifluoromethyl)phenyl))thiazole; 2-(4-fluorophenyl)-5-(thien-2-yl)thiazole; 2-(4-chlorophenyl)-5-(thien-2-yl)thiazole; 2-(4-trifluoromethylphenyl)-5-(thien-2-yl)thiazole; 5-(5-chlorothien-2-yl)-2-(4-fluorophenyl)thiazole; 2,5-bis(5-chlorothien-2-yl)-thiazole; 2-(5-chlorothien-2-yl)-5-(5-methylthien-2-yl)thiazole, and 2-(2,2-difluoro-1,3-benzodioxol-5-yl)-5-(5-methylthien-2-yl)thiazole.
Claim 11
Independent Claim
208 words
A method for controlling insects, acarids, or nematodes which comprises applying to the locus where control is desired an insecticidally, acaricidally, or nematicidally effective amount of at least one compound of the formula ##STR5## wherein W is selected from O and S; R 2 is selected from the group consisting of phenyl, naphthyl, 2,2-difluoro-1,3-benzodioxyl, phenyl substituted with at least one substituent selected from halogen, lower alkyl, lower haloalkyl, cyano, lower alkoxy, lower haloalkoxy, di(lower)alkylamino, phenylthiocarbonyl, or phenylsulfonyloxy, thienyl, and thienyl substituted with a substituent selected from halogen, lower alkyl, or thienyl; R 4 is selected from the group consisting of hydrogen, tri(lower)alkylsilyl, phenyl, halophenyl and thienyl; R 5 is selected from the group consisting of hydrogen, lower alkyl, phenyl, phenyl substituted with at least one substituent selected from halogen, lower alkyl, lower haloalkyl, lower alkoxy, phenyl, or nitro, thienyl, and thienyl substituted with a substituent selected from lower alkyl, halogen, lower hydroxyalkyl, lower haloalkylthio, lower alkylsulfonyl, lower haloalkenylthio, lower alkoxycarbonyl, or tri(lower)alkylsilyl; wherein at least one of R 2 and R 5 is an optionally substituted thienyl group, and R 4 is other than hydrogen when one of R 2 and R 5 is unsubstituted thienyl and the other of R 2 and R 5 is unsubstituted phenyl.
Claim 12
Independent Claim
208 words
A method for controlling insects, acarids, or nematodes which comprises applying to the locus where control is desired an insecticidally, acaricidally, or nematicidally effective amount of at least one compound of the formula ##STR5## wherein W is selected from O and S; R 2 is selected from the group consisting of phenyl, naphthyl, 2,2-difluoro-1,3-benzodioxyl, phenyl substituted with at least one substituent selected from halogen, lower alkyl, lower haloalkyl, cyano, lower alkoxy, lower haloalkoxy, di(lower)alkylamino, phenylthiocarbonyl, or phenylsulfonyloxy, thienyl, and thienyl substituted with a substituent selected from halogen, lower alkyl, or thienyl; R 4 is selected from the group consisting of hydrogen, tri(lower)alkylsilyl, phenyl, halophenyl and thienyl; R 5 is selected from the group consisting of hydrogen, lower alkyl, phenyl, phenyl substituted with at least one substituent selected from halogen, lower alkyl, lower haloalkyl, lower alkoxy, phenyl, or nitro, thienyl, and thienyl substituted with a substituent selected from lower alkyl, halogen, lower hydroxyalkyl, lower haloalkylthio, lower alkylsulfonyl, lower haloalkenylthio, lower alkoxycarbonyl, or tri(lower)alkylsilyl; wherein at least one of R 2 and R 5 is an optionally substituted thienyl group, and R 4 is other than hydrogen when one of R 2 and R 5 is unsubstituted thienyl and the other of R 2 and R 5 is unsubstituted phenyl.
Claim 13
Dependent Claim
28 words
The method of claim 9 wherein said compound is selected from the group consisting of 5-(5-methylthien-2-yl)-2-(4-trifluoromethylphenyl)thiazole; 5-(5-methylthien-2-yl)-2-[3,5-bis(trifluoromethyl)phenyl]thiazole; 2-(4-fluorophenyl)-5-(thien-2-yl)thiazole; 2-(4-chlorophenyl)-5-(thien-2-yl)thiazole; 2-(4-trifluoromethylphenyl)-5-(thien-2-yl)thiazole; 5-(5-chlorothien-2-yl)-2-(4-fluorophenyl)thiazole; 2-(4-methylphenyl)-5-(5-methylthien-2-yl)thiazole; 2-(5-methylthien-2-yl)-5-(thien-2-yl)thiazole; 2,5-bis-(5-chlorothien-2-yl)thiazole; 5-(5-methylthien-2-yl)-2-(thien-2-yl)thiazole; 2-(5-chlorothien-2-yl)-5-(5-methylthien-2-yl)thiazole; and 2-(2,2-difluoro-1,3-benzodioxol-5-yl)-5-(5-methylthien-2-yl)thiazole.
References Cited (Backward Citations)
US4153703A
Cited
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