US4097669A
Expired / Lapsed
US
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2-Substituted-5-trifluoromethyl-1,3,4-thiadiazoles
Assignee: Bayer AG
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Filing: 1976-07-14
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Granted: 1978-06-27
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Expires: 1996-07-14
Abstract
Abstract 2-Substituted-5-trifluoromethyl-1,3,4-thiadiazoles of the formula ##STR1## in which R is substituted alkyl, phenyl monosubstituted in the o- or m- position, polysubstituted phenyl, substituted phenylalkyl, phenylalkenyl, substituted phenylalkenyl, an optionally substituted 5-membered or 6-membered heterocyclic radical with 1 to 4 hetero-atoms selected from N and S atoms, optionally substituted benzimidazolyl or benzthiazolyl, optionally substituted naphthyl, quinolyl, cyano or one of the groups ##STR2## wherein R 1 and R 2 conjointly are a trimethylene, tetramethylene or pentamethylene group, X is oxygen or sulfur, R' and R" each independently is alkyl or, together with the nitrogen atom and optionally further hetero-atoms selected from O and N atoms, form an optionally substituted 6-membered or 7-membered ring, and N is 0, 1 or 2, Which possess fungicidal, bactericidal, arthropodicidal and insecticidal properties.
Inventors
- 👤 Josef Helmut Reisdorff
- 👤 Wilhelm Brandes
- 👤 Hans Scheinpflug
- 👤 Bernhard Homeyer
- 👤 Peter Roessler
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 05:10
CPC Classifications
C; C07; C07D; C07D285/00; C07D285/01; C07D285/02; C07D285/04; C07D285/12; C07C; C07C309/00; C07C323/00; C07D285/125
Claims Analysis
Total Claims: 9
Claim 1
Independent Claim
163 words
A 2-substituted 5-trifluoromethyl-1,3,4-thiadiazole of the formula ##STR159## in which R is phenylalkenyl; phenyl monosubstituted in the o- or m- position, polysubstituted phenyl, or substituted phenylalkenyl, the substituents being selected from alkyl with 1 to 4 carbon atoms, halogenoalkyl, halogenoalkylthio or halogenoalkylsulfonyl each with 1 or 2 carbon atoms and 2-5 halogen atoms, alkoxy, alkylcarbonyl or alkoxycarbonyl each with 1 to 4 carbon atoms in the alkyl moiety, hydroxyl, carboxyl, cyano and thiocyano or naphthyl; 5-membered or 6-membered heterocyclic radical with 1 to 4 hetero-atoms elected from N and S atoms; optionally substituted benzimidiazolyl or benzthiazolyl; optionally substituted naphthyl; quinolyl; cyano or one of the groups ##STR160## wherein R 1 and R 2 conjointly are a trimethylene, tetramethylene or pentamethylene group, X is oxygen or sulfur, R' and R" each independently is alkyl or, together with the nitrogen atom and optionally further hetero-atoms selected from O and N atoms, form an optionally substituted 6-membered or 7-membered ring, and n is 0, 1 or 1.
Claim 2
Dependent Claim
163 words
A 2-substituted 5-trifluoromethyl-1,3,4-thiadiazole of the formula ##STR159## in which R is phenylalkenyl; phenyl monosubstituted in the o- or m- position, polysubstituted phenyl, or substituted phenylalkenyl, the substituents being selected from alkyl with 1 to 4 carbon atoms, halogenoalkyl, halogenoalkylthio or halogenoalkylsulfonyl each with 1 or 2 carbon atoms and 2-5 halogen atoms, alkoxy, alkylcarbonyl or alkoxycarbonyl each with 1 to 4 carbon atoms in the alkyl moiety, hydroxyl, carboxyl, cyano and thiocyano or naphthyl; 5-membered or 6-membered heterocyclic radical with 1 to 4 hetero-atoms elected from N and S atoms; optionally substituted benzimidiazolyl or benzthiazolyl; optionally substituted naphthyl; quinolyl; cyano or one of the groups ##STR160## wherein R 1 and R 2 conjointly are a trimethylene, tetramethylene or pentamethylene group, X is oxygen or sulfur, R' and R" each independently is alkyl or, together with the nitrogen atom and optionally further hetero-atoms selected from O and N atoms, form an optionally substituted 6-membered or 7-membered ring, and n is 0, 1 or 1.
Claim 3
Dependent Claim
47 words
A compound according to claim 1, in which R is phenyl monosubstituted in the o- or m- position, polysubstituted phenyl, ##STR161## wherein R 1 and R 2 conjointly are a trimethylene, tetramethylene or pentamethylene group, and phenylalkenyl with 2 to 4 carbon atoms in the alkenyl moiety.
Claim 4
Dependent Claim
36 words
A compound according to claim 2, in which R is phenyl monosubstituted in the o- or m- position, polysubstituted phenyl, or ##STR162## wherein R 1 and R 2 conjointly are a trimethylene, tetramethylene or pentamethylene group.
Claim 5
Dependent Claim
15 words
The compound according to claim 1 wherein such compound is 2-(2'-styrylsulfonyl)-5-trifluoromethyl-1,3,4-thiadiazole of the formula ##STR163##
Claim 6
Dependent Claim
15 words
The compound according to claim 1 wherein such compound is 2-(3'-chlorophenylsulfonyl)-5-trifluoromethyl-1,3,4-thiadiazole of the formula ##STR164##
Claim 7
Dependent Claim
15 words
The compound according to claim 1 wherein such compound is 2-(3',5'-dimethylphenylsulfonyl)-5-trifluoromethyl-1,3,4-thiadiazole of the formula ##STR165##
Claim 8
Dependent Claim
15 words
The compound according to claim 1 wherein such compound is 2-(3',4'-dichlorophenylsulfonyl)-5-trifluoromethyl-1,3,4-thiadiazole of the formula ##STR166##
Claim 9
Dependent Claim
15 words
The compound according to claim 1 wherein such compound is 2-β-naphthylsulfonyl-5-trifluoromethyl-1,3,4-thiadiazole of the formula ##STR167##
References Cited (Backward Citations)
US3562284A
Cited
DE1817069A1
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-06-26 | 1981-12-26 | 1982-06-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-06-26 | 1985-12-26 | 1986-06-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-06-26 | 1989-12-26 | 1990-06-27 | $7700.00 | Window Closed / Lapsed |