Claims
- 1. An agricultural method which comprises inhibiting the growth of phytopathogenic microorganisms on a cultivated plant or curing a cultivated plant which is infested with phytopathogenic microorganisms by treating the plant, seed or locus of the plant with a microbicidally effective amount of a 2-chloro-4-trifluoromethyl-thiazol-5-carboxylic acid derivative of the formula Ia ##STR19## wherein R.sub.a is a radical --COXR.sub.1.
- X is oxygen or sulfur,
- R.sub.1 is hydrogen; C.sub.1 -C.sub.18 alkyl, which is unsubstituted or substituted by halogen, a cyano group, nitro, --YR.sub.2, A, --N(R.sub.3)COA, D, --[N(R.sub.3)].sub.m --CON[(CO).sub.m --R.sub.3 ].sub.m --(CO).sub.m R.sub.4 in which group one of the indices m must be zero, --C(X).sub.m XR.sub.7, --(X).sub.m --CXA, --PO (R.sub.5)R.sub.6, C.sub.3 -C.sub.8 cycloalkyl or C.sub.5 -C.sub.8 cycloalkenyl, which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl or methylenedioxy; R.sub.1 further represents C.sub.3 -C.sub.8 -alkenyl, C.sub.3 -C.sub.18 cycloalkyl or C.sub.3 -C.sub.18 cycloalkenyl, which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkyl, methylenedioxy or --CO(O).sub.m --R.sub.7, --COA, or --PO(R.sub.5)R.sub.6 ; R.sub.1 further represents C.sub.3 -C.sub.8 alkynyl which is unsubstituted or substituted by halogen or represents --(E).sub.m U or --(E).sub.m Q, R.sub.2 is C.sub.1 -C.sub.8 alkyl or C.sub.3 -C.sub.8 cycloalkyl, which is unsubstituted or substituted by C.sub.1 -C.sub.8 alkoxy, C.sub.1 -C.sub.8 alkylthio, C.sub.2 -C.sub.8 alkoxyalkyl halogen, cyano or --CX(X).sub.m R.sub.7, --(X).sub.m --CXA, --(X).sub.m CXR.sub.7, --N(R.sub.3)COA, A, --X--U or XQ; R.sub.2 further represents C.sub.3 -C.sub.8 alkenyl or C.sub.3 -C.sub.8 cycloalkenyl, which is unsubstituted or substituted by halogen or represents --(E).sub.m U or --(E).sub.m Q;
- m is zero or one;
- Y is oxygen, sulfur, SO or SO.sub.2 ;
- A is a radical --N(R.sub.3)R.sub.4 ;
- D is a radical --N(R.sub.3)N(R.sub.4)(CO).sub.m R.sub.3 ;
- R.sub.3 and R.sub.4 independently of each other represent hydrogen, C.sub.1 -C.sub.8 alkyl or C.sub.3 -C.sub.8 cycloalkyl, which is unsubstituted or substituted by C.sub.1 -C.sub.8 alkoxy, C.sub.2 -C.sub.8 alkoxyalkoxy, C.sub.1 -C.sub.8 alkylthio, cyano, --COOR.sub.10, C.sub.1 -C.sub.4 alkylcarbamoyl, di-C.sub.1 -C.sub.4 alkylcarbamoyl, piperidinocarbonyl, pyrrolidinocarbonyl, piperidino or pyrrolidino; R.sub.3 and R.sub.4 further represent C.sub.3 -C.sub.8 alkenyl or C.sub.3 -C.sub.8 cycloalkenyl which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.8 alkoxy, C.sub.3 -C.sub.8 cycloalkyl or cyano, --COOR.sub.7, C.sub.1 -C.sub.4 alkylcarbamoyl or piperidinocarbamoyl; R.sub.3 and R.sub.4 represent further C.sub.3 -C.sub.8 alkynyl, which is unsubstituted or substituted by U, or R.sub.3 and R.sub.4 represent a radical --(E).sub.m U or --(E).sub.m Q;
- R.sub.3 and R.sub.4 together with the nitrogen atom, to which they are bound form a heterocycle selected from among pyrrolidine, 2-oxo-pyrrolidine, piperidine, morpholine, thiomorpholine, 2-oxo-thiomorpholine and azepine, which may be substituted by halogen, cyano, C.sub.1 -C.sub.8 alkoxy, amino, C.sub.1 -C.sub.4 -alkylamino di-C.sub.1 -C.sub.4 alkylamino or --COOR.sub.7 ;
- R.sub.5 and R.sub.6 are independently of each other are hydrogen or C.sub.1 -C.sub.4 alkoxy;
- R.sub.7 is hydrogen, C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.3 -C.sub.8 alkenyl, C.sub.2 -C.sub.8 alkoxyalkyl, C.sub.3 -C.sub.8 alkoxyalkoxyalkyl, C.sub.1 -C.sub.4 haloalkyl, --(C.sub.1 -C.sub.3 alkylene).sub.m U, --(C.sub.1 -C.sub.3 alkylene).sub.m Q, C.sub.1 -C.sub.4 haloalkoxy;
- U is phenyl or naphthyl, which is unsubstituted or substituted one to three times by halogen C.sub.1 -C.sub.4 alkyl, --Y--C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkoxy, cyano, nitro, carboxyl, --COOR.sub.7, --CONH.sub.2, --CONHR.sub.7, --CON(R.sub.7), --SO.sub.2 NHR.sub.7, --SO.sub.2 N(R.sub.7).sub.2, pyrrolidino, piperidino, pyrrolidino, carbonyl or piperidinocarbonyl;
- E is a C.sub.1 -C.sub.8 alkylene or C.sub.2 -C.sub.8 alkylene chain, which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkoxy or by a group --CO(O).sub.m R.sub.7, --(CO).sub.m A --(CO).sub.m Q;
- Q is a heterocycle which is bound via a carbon atom and is selected from among furan, tetrahydrofuran pyran, pentahydropyran, dioxolan, dioxan, benzdioxan, dihydrobenzdioxan, thienyl, thiazol, which may be substituted by halogen or methyl.
- 2. A method of claim 1 wherein X is O.
- 3. A method of claim 1 wherein the 2-chloro-4-trifluoromethyl-thiazol-5-carboxylic acid derivative is selected from the group consisting of 2-chloro-4-trifluoromethyl-thiazol-5-carboxylic acid, 2-chloro-4-trifluoromethyl-thiazol-5-carboxylic acid-benzyl ester, 2-chloro-4-trifluoromethyl-thiazol-5-carboxylic acid-ethyl ester, 2-chloro-4-trifluoromethyl-thiazol-5-carboxylic acid-(2-cyanoethyl)ester, 2-chloro-4-trifluoromethyl-thiazol-5-carboxylic acid-(2-phenoxyethyl)ester, 2-chloro-4-trifluoromethyl-thiazol-5-carboxylic acid-(2-phenylthioethyl)ester, 2-chloro-4-trifluoromethyl-thiazol-5-carboxylic acid-(diphenylmethyl)ester, 2-chloro-4-trifluoromethyl-thiazol-5-carboxylic acid-(.alpha.-cyanobenzyl)ester, 2-chloro-4-trifluoromethyl-thiazol-5-carboxylic acid-(.alpha.-benzoyl-benzyl)ester, 2-chloro-4-trifluoromethyl-thiazol-5-carboxylic acid-(2-methylsulfonyl-ethyl)ester, 2-chloro-4-trifluoromethyl-thiazol-5-carboxylic acid-(2,3,5,6-diepoxycyclohexan-1-yl)ester, 2-chloro-4-trifluoromethyl-thiazol-5-carboxylic acid-(2,2-dimethyl-1,3-dioxolan-2-yl-methyl)ester, 2-chloro-4-trifluoromethyl-thiazol-5-carboxylic acid-azepinomethylester, 2-chloro-4-trifluoromethyl-thiazol-5-carboxylic acid-(piperidinoeth-1-yl)-ester, 2-chloro-4-trifluoromethyl-thiazol-5-carboxylic acid-[2-(4-methylthiazol-5-yl)ethyl]ester, 2-chloro-4-trifluoromethyl-thiazol-5-carboxylic acid-[2-(5-methylthiazol-4-yl)ethyl]ester, 2-chloro-4-trifluoromethyl-thiazol-5-carboxylic acid-[2-piperidinocarbonyl-ethyl)ester, 2-chloro-4-trifluoromethyl-thiazol-5-carboxylic acid-(piperidinocarbonyl-eth-1-yl)ester.
- 4. A method of claim 1 wherein the 2-chloro-4-trifluoromethyl-thiazol-5-carboxylic acid derivative is of the formula Ic ##STR20## wherein R.sub.1 is C.sub.1 -C.sub.18 alkyl or C.sub.3 -C.sub.18 cycloalkyl unsubstituted or C.sub.1 -C.sub.18 -alkyl substituted by halogen C.sub.1 -C.sub.8 alkoxy, C.sub.1 -C.sub.8 alkylthio, C.sub.2 -C.sub.8 alkoxyalkoxy nitro, cyano or A--, CX(X).sub.m R.sub.7, --N(R.sub.3)COA,
- A is --N(R.sub.3)R.sub.4 or --(E).sub.m U
- m is zero or one R.sub.3 and R.sub.4 independently of each other are hydrogen, C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.8 -alkenyl or --(E).sub.m --U or R.sub.3 and R.sub.4 together with the nitrogen atom to which they are bound form a heterocycle selected from the group consisting of pyrrolidine, piperidine, azepine and morpholine
- R.sub.7 is hydrogen or C.sub.1 -C.sub.10 alkyl
- E is C.sub.1 -C.sub.8 alkylene or C.sub.2 -C.sub.8 alkenylene chain
- U is phenyl or naphthyl, which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkoxy or --CO(O).sub.m R.sub.7, and
- X is oxygen or sulfur.
- 5. A method of claim 1 wherein the cultivated plant is selected form the group consisting of beets, pomes, drupes and soft fruits, leguminous plants, oil plants, cucumber plants, fiber plants, vegetables, lauraceae, ornamentals, tobacco, nuts, coffee, sugar cane, tea, vines, hops, bananas and natural rubber plants.
- 6. A method of claim 1 wherein the cultivated plant is a cereal selected from the group consisting of wheat, barley, rye and oats.
- 7. A method according to claim 1 wherein the microorganisms are phytophatogenic fungi or soil borne phytopathogenic bacteries.
- 8. A method according to claim 1 which comprises treating seeds.
- 9. A method according to claim 1 which comprises treating rice plants.
- 10. A method of claim 1 wherein a cultivated plant, which is infested with phytopathogenic microorganism, is cured.
Priority Claims (1)
Number |
Date |
Country |
Kind |
351/87 |
Jan 1987 |
CHX |
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Parent Case Info
This is a continuation-in-part of application Ser. No. 366,166, filed Apr. 11, 1989, now U.S. Pat. No. 4,992,434, issued Feb. 12, 1991, which in turn is a continuation-in-part of application Ser. No. 147,388 filed Jan. 25, 1988, now abandoned.
US Referenced Citations (10)
Foreign Referenced Citations (4)
Number |
Date |
Country |
44201 |
Jan 1982 |
EPX |
0279239 |
Aug 1988 |
EPX |
0335831 |
Oct 1989 |
EPX |
2020662 |
Nov 1979 |
GBX |
Non-Patent Literature Citations (1)
Entry |
Craig et al. Phytopathology, 77-1530 (1987). |
Continuation in Parts (2)
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Number |
Date |
Country |
Parent |
336166 |
Apr 1989 |
|
Parent |
147388 |
Jan 1988 |
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