US4894380A
Expired / Lapsed
US
⏱️ 0.0 years remaining
2-mercapto-5-pyridyl-1,3,4-oxadiazoles and 2-mercapto-5-pyridyl-1,3,4-thiadiazoles of the formula I
Assignee: Novartis Corp
•
Filing: 1988-03-25
•
Granted: 1990-01-16
•
Expires: 2008-03-25
Abstract
Abstract The invention relates to 2-mercapto-5-pyridyl-1,3,4-oxadiazoles and 2-mercapto-5-pyridyl-1,3,4-thiadiazoles of the formula I ##STR1## wherein X is oxygen or sulfur, R' is C 1 -C 3 alkyl which is substituted by bromine, fluorine, C 1 -C 3 alkoxy or cyano; unsubstituted or halogen-substituted C 3 -C 7 alkenyl; unsubstituted or halogen-substituted C 4 -C 7 alkynyl, R is C 1 -C 3 alkyl, unsubstituted C 1 -C 3 alkoxy or C 1 -C 3 alkoxy which is substituted by halogen or C 1 -C 3 alkoxy; unsubstituted or halogen-substituted C 3 -C 7 alkenyl; C 3 -C 7 alkynyl, C 1 -C 3 alkylthio, halogen, cyano, hydroxy, amino or amino which is substituted by one or two C 1 -C 3 alkyl groups; or is aminocarbonyl; and n is 0, 1, 2, 3 or 4, to the preparation of the compounds of formula I and to novel intermediates for the synthesis of these compounds. The compounds of formula I have nematicidal properties. The invention further relates to nematicidal compositions which contain at least one compound of formula I as active component, and to methods of using said compounds and of the compositions containing them for controlling nematodes.
Inventors
- 👤 Robert Nyfeler
- 👤 Wolfgang Eckhardt
- 👤 Ernst Beriger
- 👤 Odd Kristiansen
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 04:53
CPC Classifications
C; C07; C07D; C07D413/00; C07D413/02; C07D413/04; A; A01; A01N; A01N43/00; A01N43/72; A01N43/82; C07D417/00; C07D417/02; C07D417/04
Claims Analysis
Total Claims: 26
Claim 1
Independent Claim
138 words
A 2-mercapto-5-pyridyl-1,3,4-oxadiazole or 2-mercapto-5-pyridyl-1,3,4-thiadiazole of the formula (I) ##STR64## wherein X is oxygen or sulfur, R' is C 1 -C 3 alkyl which is substituted by bromine, fluorine, C 1 -C 3 alkoxy or cyano; unsubstituted or halogen-substituted C 3 -C 7 alkenyl; halogen-substituted C 4 -C 7 alkynyl, R is C 1 -C 3 alkyl; or halo-C 1 -C 3 alkyl unsubstituted C 1 -C 3 alkoxy or C 1 -C 3 alkoxy which is substituted by halogen or C 1 -C 3 alkoxy; unsubstituted or halogen-substituted C 3 -C 7 alkenyl; C 3 -C 7 alkynyl, C 1 -C 3 alkylthio; halogen; cyano; hydroxy, amino or amino which is substituted by one or two C 1 -C 3 alkyl groups; or is aminocarbonyl; and n is 0, 1, 2, 3 or 4, or a salt thereof.
Claim 2
Dependent Claim
138 words
A 2-mercapto-5-pyridyl-1,3,4-oxadiazole or 2-mercapto-5-pyridyl-1,3,4-thiadiazole of the formula (I) ##STR64## wherein X is oxygen or sulfur, R' is C 1 -C 3 alkyl which is substituted by bromine, fluorine, C 1 -C 3 alkoxy or cyano; unsubstituted or halogen-substituted C 3 -C 7 alkenyl; halogen-substituted C 4 -C 7 alkynyl, R is C 1 -C 3 alkyl; or halo-C 1 -C 3 alkyl unsubstituted C 1 -C 3 alkoxy or C 1 -C 3 alkoxy which is substituted by halogen or C 1 -C 3 alkoxy; unsubstituted or halogen-substituted C 3 -C 7 alkenyl; C 3 -C 7 alkynyl, C 1 -C 3 alkylthio; halogen; cyano; hydroxy, amino or amino which is substituted by one or two C 1 -C 3 alkyl groups; or is aminocarbonyl; and n is 0, 1, 2, 3 or 4, or a salt thereof.
Claim 3
Dependent Claim
34 words
A 2-mercapto-5-(pyrid-2-yl) 1,3,4-oxadiazole according to claim 1 of the formula ##STR65## wherein R' is difluoromethyl, the substituents R 1 , R 2 and R 3 are hydrogen and R 4 is aminocarbonyl or hydroxy.
Claim 4
Dependent Claim
29 words
A 2-mercapto-5-(pyrid-2-yl)-1,3,4-oxadiazole according to claim 1 of the formula ##STR66## wherein R' difluoromethyl or cyanomethyl and R 1 , R 2 , R 3 and R 4 are hydrogen.
Claim 5
Dependent Claim
5 words
2-Difluoromethylthio-5-(pyrid-2-yl)-1,3,4-oxadiazole according to claim 1.
Claim 6
Dependent Claim
56 words
A 2-mercapto-5-(pyrid-2-yl)thiadiazole according to claim 1 of the formula ##STR67## wherein R' is C 1 -C 3 alkyl which is substituted by bromine, fluorine or cyano; allyl or halogen-substituted allyl; R 1 , R 2 , R 3 and R 4 are each independently hydrogen, methyl, difluoromethyl, trifluoromethyl, methoxy, methylmercapto, chlorine, cyano, hydroxy, amino or aminocarbonyl.
Claim 7
Dependent Claim
29 words
A compound according to claim 5, wherein R 1 and R 2 are each independently of the other hydrogen or chlorine and R 2 and R 3 are hydrogen.
Claim 8
Dependent Claim
33 words
A compound according to claim 5, wherein R' is difluoromethyl, R 1 , R 2 and R 3 are hydrogen and R 4 is methyl, trifluoromethyl, methoxy, chlorine, cyano, aminocarbonyl, hydroxy or amino.
Claim 9
Dependent Claim
40 words
A compound according to claim 5, wherein R' is difluoromethyl, one of the substituents R 1 , R 2 and R 3 is methyl, chlorine, methoxy or methylmercapto and the other two substituents are hydrogen and R 4 is hydrogen.
Claim 10
Dependent Claim
34 words
A compound according to claim 5, wherein R' is difluoromethyl, R 1 and R 4 are each independently of the other hydrogen, chlorine, methoxy or hydroxy, and R 2 and R 3 are hydrogen.
Claim 11
Dependent Claim
5 words
2-Difluoromethylthio-5-(pyrid-2-yl)-1,3,4-thiadiazole according to claim 9.
Claim 12
Dependent Claim
42 words
A 2-mercapto-5-(pyrid-3-yl)oxadiazole according to claim 1 of the formula ##STR68## wherein R' is difluoromethyl and one of the substituents R 1 , R 2 , R 3 and R 4 is methyl, methylmercapto or halogen and the other three sustituents are hydrogen.
Claim 13
Dependent Claim
37 words
A 2-mercapto-5-(pyrid-3-yl)oxadiazole according to claim 1 of the formula ##STR69## wherein R' is difluoromethyl and R 1 and R 4 are each independently of the other methyl or chlorine and R 2 and R 3 are hydrogen.
Claim 14
Dependent Claim
35 words
A 2-mercapto-5-(pyrid-3-yl)oxadiazole according to claim 1 of the formula ##STR70## wherein R' is difluoromethyl, R 1 and R 4 are chlorine and one of the substituents R 2 and R 3 is hydrogen or chlorine.
Claim 15
Dependent Claim
28 words
A 2-mercapto-5-(pyrid-3-yl)oxadiazole according to claim 1 of the formula ##STR71## wherein R' is difluoromethyl and R 1 , R 2 , R 3 and R 4 are hydrogen.
Claim 16
Dependent Claim
30 words
A 2-mercapto-5-(pyrid-3-yl)thiadiazole according to claim 1 of the formula ##STR72## wherein R' is difluoromethyl or difluoromethyldifluoromethyl and R 1 , R 2 , R 3 and R 4 are hydrogen.
Claim 17
Dependent Claim
46 words
A 2-mercapto-5-(pyrid-3-yl)-thiadiazole according to claim 1 of the formula ##STR73## wherein R' is difluoromethyl, R 1 is hydrogen, C 1 -C 3 alkyl or chlorine, R 2 is hydrogen and R 3 and R 4 are each independently of the other hydrogen or chlorine or methoxy.
Claim 18
Dependent Claim
36 words
A 2-mercapto-5-(pyrid-3-yl)thiadiazole of the formula ##STR74## according to claim 16, wherein R' is difluoromethyl, R 1 , R 2 and R 4 are each independently hydrogen, chlorine, bromine, methylthio or amino, and R 3 is hydrogen.
Claim 19
Dependent Claim
5 words
2-Difluoromethylthio-5-(pyrid-3-yl)-1,2,4-thiadiazole according to claim 17.
Claim 20
Dependent Claim
31 words
A 2-mercapto-5(pyrid-4-yl)-oxadiazole according to claim 1 of the formula ##STR75## wherein R' is difluoromethyl, difluoromethyldifluoromethyl or cyanomethyl, and R 1 , R 2 , R 3 and R 4 are hydrogen.
Claim 21
Dependent Claim
18 words
A 2-mercapto-5-(pyrid-4-yl)-thiadiazole according to claim 1 of the formula ##STR76## wherein R 2 and R 3 are hydrogen.
Claim 22
Dependent Claim
43 words
A compound according to claim 20, wherein R' is difluoromethyl, difluoromethyldifluoromethyl, cyanomethyl or 2-bromoallyl, R 1 is hydrogen, C 1 -C 4 alkyl, chlorine, methoxy or methylmercapto, R 4 is hydrogen, methyl, chlorine, methoxyethoxy, trifluoromethylmethoxy, methylmercapto, amino or C 1 -C 3 monoalkylamino.
Claim 23
Dependent Claim
5 words
Difluoromethylthio-5-(pyrid-4-yl)-1,3,4-thiadiazole according to claim 21.
Claim 24
Dependent Claim
32 words
A pesticidal composition for controlling nematodes or for protecting plants from attack by nematodes, which composition contains as active component a pesticidally active amount of at least one compound of claim 1.
Claim 25
Independent Claim
154 words
A method of controlling nematodes or of protecting cultivated plants from attack by nematodes, which method comprises applying to the plant or to the locus thereof a compound of the formula ##STR77## wherein X is oxygen or sulfur R is hydrogen, C 1 -C 3 alkyl, C 1 -C 3 alkoxy which is substituted by halogen or C 1 -C 3 alkoxy; C 3 -C 7 alkenyl or halogen-substituted C 3 -C 7 alkenyl; C 3 -C 7 alkynyl; C 1 -C 3 alkylthio; cyano, halogen, hydroxy; amino or amino which is substituted by one or two C 1 -C 3 alkyl groups; or is aminocarbonyl, R' is C 1 -C 3 alkyl which is substituted by halogen, C 1 -C 3 alkoxy or cyano; C 3 -C 7 alkenyl or halogen-substituted C 3 -C 7 alkenyl; unsubstituted or substituted C 3 -C 7 alkynyl; and n is 0, 1, 2, 3 or 4.
Claim 26
Independent Claim
154 words
A method of controlling nematodes or of protecting cultivated plants from attack by nematodes, which method comprises applying to the plant or to the locus thereof a compound of the formula ##STR77## wherein X is oxygen or sulfur R is hydrogen, C 1 -C 3 alkyl, C 1 -C 3 alkoxy which is substituted by halogen or C 1 -C 3 alkoxy; C 3 -C 7 alkenyl or halogen-substituted C 3 -C 7 alkenyl; C 3 -C 7 alkynyl; C 1 -C 3 alkylthio; cyano, halogen, hydroxy; amino or amino which is substituted by one or two C 1 -C 3 alkyl groups; or is aminocarbonyl, R' is C 1 -C 3 alkyl which is substituted by halogen, C 1 -C 3 alkoxy or cyano; C 3 -C 7 alkenyl or halogen-substituted C 3 -C 7 alkenyl; unsubstituted or substituted C 3 -C 7 alkynyl; and n is 0, 1, 2, 3 or 4.
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) | 1993-01-15 | 1993-07-17 | 1994-01-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1997-01-15 | 1997-07-17 | 1998-01-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2001-01-15 | 2001-07-17 | 2002-01-16 | $7700.00 | Window Closed / Lapsed |