US5162349A
Expired / Lapsed
US
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Nematocidal and fungicidal compositions
Assignee: Novartis Corp
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Filing: 1989-09-18
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Granted: 1992-11-10
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Expires: 2009-09-18
Abstract
Abstract Mercapto-bis-[1,3,4-oxa- and -thiadiazoles] ##STR1## in which X 1 and X 2 independently of one another are oxygen or sulfur, R 1 is hydrogen or C 1 -C 5 alkyl which is unsubstituted or substituted by halogen, C 1 -C 3 alkoxy or cyano; C 3 -C 7 alkenyl which is unsubstituted or substituted by halogen; or C 3 -C 7 alkynyl which is unsubstituted or substituted by halogen, R 2 is hydrogen, C 1 -C 5 alkyl, C 1 -C 3 alkoxy which is unsubstituted or substituted by halogen, C 1 -C 3 alkylthio which is unsubstituted or substituted by halogen, C 3 -C 7 alkenylthio which is unsubstituted or substituted by halogen, C 3 -C 7 alkylnylthio which is unsubstituted or substituted by halogen, --SH, phenyl which is unsubstituted or substituted by halogen or ##STR2## in which R 3 and R 4 are C 1 -C 3 alkyl, and processes for the preparation of the compounds of the formula I are described. The compounds of the formula I have nematocidal and microbicidal properties. Nematocidal compositions which contain at least one active substance of the formula I as the active substance and furthermore processes for the use of the active substances and the compositions in combating nematodes and fungi which are harmful to plants are described.
Inventors
- 👤 Ernst Beriger
- 👤 Wolfgang Eckhardt
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 04:35
CPC Classifications
C; C07; C07D; C07D271/00; C07D271/02; C07D271/10; C07D271/113; A; A01; A01N; A01N43/00; A01N43/72; A01N43/82; C07D285/00; C07D285/01; C07D285/02; C07D285/04; C07D285/12; C07D285/125; C07D417/00; C07D417/02; C07D417/04
Claims Analysis
Total Claims: 41
Claim 1
Independent Claim
160 words
A mercapto-bis-(1,3,4-oxa- or -thiadiazole) of the formula I ##STR15## in which X 1 and X 2 independently of one another are oxygen or sulfur, R 1 is hydrogen or C 1 -C 5 alkyl which is unsubstituted or substituted by halogen, C 1 -C 3 alkoxy or cyano; C 3 -C 7 alkenyl which is unsubstituted or substituted by halogen; or C 3 -C 7 alkynyl which is unsubstituted or substituted by halogen, R 2 is hydrogen, C 1 -C 5 alkyl, C 1 -C 3 alkoxy which is unsubstituted or substituted by halogen, C 1 -C 3 alkylthio which is unsubstituted or substituted by halogen, C 3 -C 7 alkenylthio which is unsubstituted or substituted by halogen, C 3 -C 7 alkynylthio which is unsubstituted or substituted by halogen, --SH, phenyl which is unsubstituted or substituted by halogen or ##STR16## in which R 3 and R 4 are C 1 -C 3 alkyl, and a salt of this compound.
Claim 2
Dependent Claim
160 words
A mercapto-bis-(1,3,4-oxa- or -thiadiazole) of the formula I ##STR15## in which X 1 and X 2 independently of one another are oxygen or sulfur, R 1 is hydrogen or C 1 -C 5 alkyl which is unsubstituted or substituted by halogen, C 1 -C 3 alkoxy or cyano; C 3 -C 7 alkenyl which is unsubstituted or substituted by halogen; or C 3 -C 7 alkynyl which is unsubstituted or substituted by halogen, R 2 is hydrogen, C 1 -C 5 alkyl, C 1 -C 3 alkoxy which is unsubstituted or substituted by halogen, C 1 -C 3 alkylthio which is unsubstituted or substituted by halogen, C 3 -C 7 alkenylthio which is unsubstituted or substituted by halogen, C 3 -C 7 alkynylthio which is unsubstituted or substituted by halogen, --SH, phenyl which is unsubstituted or substituted by halogen or ##STR16## in which R 3 and R 4 are C 1 -C 3 alkyl, and a salt of this compound.
Claim 3
Dependent Claim
144 words
A mercapto-bis-(1,3,4-oxa- or -thiadiazole) according to claim 1, in which R 1 is C 1 -C 5 alkyl which is unsubstituted or substituted by halogen, C 1 -C 3 alkoxy or cyano; C 3 -C 7 alkenyl which is unsubstituted or substituted by halogen; or C 3 -C 7 alkynyl which is unsubstituted or substituted by halogen, R 2 is hydrogen, C 1 -C 5 alkyl, C 1 -C 3 alkoxy which is unsubstituted or substituted by halogen, C 1 -C 3 alkylthio which is unsubstituted or substituted by halogen, C 3 -C 7 alkenylthio which is unsubstituted or substituted by halogen, C 3 -C 7 alkynylthio which is unsubstituted or substituted by halogen, --SH, phenyl which is unsubstituted or substituted by halogen or ##STR17## in which R 3 and R 4 are C 1 -C 3 alkyl, or a salt of this compound.
Claim 4
Dependent Claim
103 words
A mercapto-bis-(1,3,4-oxa- or -thiadiazole) according to claim 2, in which X 1 and X 2 independently of one another are oxygen or sulfur, R 1 is C 1 -C 5 alkyl which is unsubstituted or substituted by halogen, C 1 -C 3 alkoxy or cyano; C 3 -C 7 alkenyl which is unsubstituted or substituted by halogen; or C 3 -C 7 alkynyl which is unsubstituted or substituted by halogen and R 2 is hydrogen, C 1 -C 5 alkyl or ##STR18## in which R 3 and R 4 are C 1 -C 3 alkyl, and R 4 a salt of this compound.
Claim 5
Dependent Claim
32 words
A 2-mercapto-5-(1,3,4-oxadiazol-5-yl)-1,3,4-oxadiazole of the formula Ia ##STR19## according to claim 3, in which R 1 is methyl, difluoromethyl, trifluoromethyl, cyanomethyl, allyl, propargyl or 3,4,4-trifluoro-3-buten-1-yl and R 2 is hydrogen, methyl or dimethylamino.
Claim 6
Dependent Claim
14 words
A 2-mercapto-5-(1,3,4-oxadiazol-5-yl)-1,3,4-oxadiazole according to claim 4, in which R 1 is difluoromethyl or 3,4,4-trifluoro-3-buten-1-yl.
Claim 7
Dependent Claim
5 words
2-Difluoromethylthio-5-(2-methyl-1,3,4-oxadiazol-5-yl)-1,3,4-oxadiazole according to claim 5.
Claim 8
Dependent Claim
5 words
2-(3,4,4-Trifluoro-3-buten-1-ylthio)-5-(2-methyl-1,3,4-oxadiazol-5-yl)-1,3,4-oxadiazole according to claim 5.
Claim 9
Dependent Claim
32 words
A 2-mercapto-5-(1,3,4-thiadiazol-5-yl)-1,3,4-oxadiazole of the formula Ib ##STR20## according to claim 3, in which R 1 is methyl, difluoromethyl, trifluoromethyl, cyanomethyl, allyl, propargyl or 3,4,4-trifluoro-3-buten-1-yl and R 2 is hydrogen, methyl or dimethylamino.
Claim 10
Dependent Claim
5 words
2-Difluoromethylthio-5-(2-methyl-1,3,4-oxadiazol-5-yl)-1,3,4-thiadiazole according to claim 8.
Claim 11
Dependent Claim
5 words
2-(3,4,4-Trifluoro-3-buten-1-ylthio)-5-(2-methyl-1,3,4-oxadiazol-5-yl)-1,3,4-thiadiazole according to claim 8.
Claim 12
Dependent Claim
32 words
A 2-mercapto-5-(1,3,4-oxadiazol-5-yl)-1,3,4-thiadiazole of the formula Ic ##STR21## according to claim 3, in which R 1 is methyl, difluoromethyl, trifluoromethyl, cyanomethyl, allyl, propargyl or 3,4,4-trifluoro-3-buten-1-yl and R 2 is hydrogen, methyl or dimethylamino.
Claim 13
Dependent Claim
32 words
A 2-mercapto-5-(1,3,4-oxadiazol-5-yl)-1,3,4-thiadiazole of the formula Id ##STR22## according to claim 3, in which R 1 is methyl, difluoromethyl, trifluoromethyl, cyanomethyl, allyl, propargyl or 3,4,4-trifluoro-3-buten-1-yl and R 2 is hydrogen, methyl or dimethylamino.
Claim 14
Dependent Claim
5 words
2-(3,4,4-Trifluoro-3-buten-1-ylthio)-5-(2-methylthio-1,3,4-thiadiazol-5-yl)-1,3,4-thiadiazole according to claim 2.
Claim 15
Dependent Claim
5 words
2-(3,4,4-Trifluoro-3-buten-1-ylthio)-5-(2-methylthio-1,3,4-thiadiazol-5-yl)-1,3,4-oxadiazole according to claim 2.
Claim 16
Dependent Claim
5 words
2-(Difluoromethylthio)-5-(2-methyl-1,3,4-oxadiazol-5-yl)-1,3,4-thiadiazole according to claim 11.
Claim 17
Dependent Claim
5 words
2-(3,4,4-Trifluoro-3-buten-1-ylthio)-5-(2-methyl-1,3,4-oxadiazol-5-yl)-1,3,4-thiadiazole according to claim 11.
Claim 18
Dependent Claim
24 words
A compound according to claim 1, in which R 1 is difluoromethylthio or 3,4,4-trifluoro-3-buten-1-yl and R 2 is difluoromethylthio, 3,4,4-trifluoro-3-buten-1-yl or the thiol radical.
Claim 19
Dependent Claim
5 words
2-(3,4,4-Trifluoro-3-buten-1-ylthio)-5-(2-mercapto-1,3,4-oxadiazol-5-yl)-1,3,4-thiadiazole according to claim 11.
Claim 20
Dependent Claim
5 words
2-(3,4,4-Trifluoro-3-buten-1-ylthio)-5-1,3,4-thiadiazole according to claim 11.
Claim 21
Dependent Claim
5 words
2-(3,4,4-Trifluoro-3-buten-1-ylthio)-5-(2-phenyl-1,3,4-oxadiazol-5-yl)-1,3,4-thiadiazole according to claim 11.
Claim 22
Dependent Claim
5 words
2-(3,4,4-Trifluoro-3-buten-1-ylthio)-5-(2-phenyl-1,3,4-oxadiazol-5-yl)-1,3,4-oxadiazole according to claim 11.
Claim 23
Dependent Claim
5 words
2-(3,4,4-Trifluoro-3-buten-1-ylthio)-5-(2-difluoromethylthio-1,3,4-oxadiazol-5-yl)-1,3,4-thiadiazole according to claim 11.
Claim 24
Dependent Claim
5 words
2-(3,4,4-Trifluoro-3-buten-1-ylthio)-5-1,3,4-oxadiazole according to claim 11.
Claim 25
Dependent Claim
45 words
A compound of the formula IIa ##STR23## in which R 2 , X 1 and X 2 are as defined according to claim 1 under formula I, with the proviso that R 2 is other than hydrogen if X 1 and X 2 are sulfur.
Claim 26
Dependent Claim
39 words
A compound of the formula IIa, ##STR24## wherein R 2 , X 1 and X 2 are as defined according to claim 1 under formula I, with the proviso that X 1 and X 2 are not simultaneously sulfur.
Claim 27
Dependent Claim
33 words
A pest control composition for controlling or preventing infestation of plants by nematodes and fungi, which contains at least one compound of the formula I according to claim 1 as the active component.
Claim 28
Dependent Claim
13 words
A composition according to claim 26, which contains 2-difluoromethylthio-5-(2-methyl-1,3,4-oxadiazol-5-yl)-1,3,4-oxadiazole as the active component.
Claim 29
Dependent Claim
13 words
A composition according to claim 26, which contains 2-(3,4,4-trifluoro-3-buten-1-ylthio)-5-(2-methyl-1,3,4-oxadiazol-5-yl)-1,3,4-oxadiazole as the active component.
Claim 30
Dependent Claim
13 words
A composition according to claim 26, which contains 2-difluoromethylthio-5-(2-methyl-1,3,4-oxadiazol-5-yl)-1,3,4-thiadiazole as the active component.
Claim 31
Dependent Claim
13 words
A composition according to claim 26, which contains 2-(3,4,4-trifluoro-3-buten-1-ylthio)-5-(2-methyl-1,3,4-oxadiazol-5-yl)-1,3,4-thiadiazole as the active component.
Claim 32
Dependent Claim
35 words
A composition according to claim 29, which contains 0.1 to 95% of an active substance of the formula I, 99.8 to 5% of a solid or liquid additive and 0.1 to 25% of a surfactant.
Claim 33
Dependent Claim
146 words
A composition of claim 26 wherein R 1 is C 1 -C 5 alkyl which is unsubstituted or substituted by halogen, C 1 -C 3 alkoxy or cyano; C 3 -C 7 alkenyl which is unsubstituted or substituted by halogen; or C 3 -C 7 alkynyl which is unsubstituted or substituted by halogen, R 2 is hydrogen, C 1 -C 5 alkyl, C 1 -C 3 alkoxy which is unsubstituted or substituted by halogen, C 1 -C 3 alkylthio which is unsubstituted or substituted by halogen, C 3 -C 7 alkenylthio which is unsubstituted or substituted by halogen, C 3 -C 7 alkynylthio which is unsubstituted or substituted by halogen, R 2 is also --SH, phenyl which is unsubstituted or substituted by halogen or R 2 ##STR25## in which R 3 and R 4 are C 1 -C 3 , or a salt of this compound.
Claim 34
Dependent Claim
17 words
A composition of claim 32 wherein R 2 is hydrogen, C 1 -C 5 -alkyl or ##STR26##
Claim 35
Dependent Claim
35 words
A composition according to claim 26 which contains 0.1 to 99% of an active substance of the formula I, 99.9 to 1% of a solid or liquid additive and 0 to 25% of a surfactant.
Claim 36
Dependent Claim
33 words
A method of controlling or preventing infestation of crop plants by nematodes and fungi, which comprises applying a compound of the formula I according to claim 1 onto the plants or their location.
Claim 37
Dependent Claim
146 words
A method of claim 35 wherein R 1 is C 1 -C 5 alkyl which is unsubstituted or substituted by halogen, C 1 -C 3 alkoxy or cyano; C 3 -C 7 alkenyl which is unsubstituted or substituted by halogen; or C 3 -C 7 alkynyl which is unsubstituted or substituted by halogen, R 2 is hydrogen, C 1 -C 5 alkyl, C 1 -C 3 alkoxy which is unsubstituted or substituted by halogen, C 1 -C 3 alkylthio which is unsubstituted or substituted by halogen, C 3 -C 7 alkenylthio which is unsubstituted or substituted by halogen, C 3 -C 7 alkynylthio which is unsubstituted or substituted by halogen, R 2 is also --SH, phenyl which is unsubstituted or substituted by halogen or R 2 ##STR27## in which R 3 and R 4 are C 1 -C 3 , or a salt of this compound.
Claim 38
Dependent Claim
17 words
A method of claim 36 wherein R 2 is hydrogen, C 1 -C 5 alkyl or ##STR28##
Claim 39
Dependent Claim
16 words
A method according to claim 36, wherein the nematodes are species which are parasitic to plants.
Claim 40
Dependent Claim
15 words
A method according to claim 38 against nematodes of the genus Meloidogyne, Heterodera or Globodera.
Claim 41
Dependent Claim
19 words
A method according to claim 35 against fungi of the genera Pythium, Rhizoctonia, Fungi imperfecti, Basidomycetes, Ascomycetes and Oomycetes.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1995-11-10 | 1996-05-11 | 1996-11-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1999-11-10 | 2000-05-11 | 2000-11-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2003-11-10 | 2004-05-11 | 2004-11-10 | $7700.00 | Window Closed / Lapsed |