Claims
- 1. A compound of the formula I ##STR52## in which R.sub.1, R.sub.2 and R.sub.3 independently of one another are hydrogen, halogen, methyl, methoxy or methylthio; A is --OR.sub.4, --SR.sub.4, --N(R.sub.5)R.sub.6, --N(R.sub.7)--N(R.sub.5)R.sub.6, --O-N.dbd.C(R.sub.8)R.sub.9, --N(R.sub.7)--OR.sub.10, or ##STR53## R.sub.4 is C.sub.1 -C.sub.18 alkyl, C.sub.3 -C.sub.35 alkyl which is interrupted by an oxygen or sulfur atom, C.sub.1 -C.sub.8 alkyl which is substituted by halogen or --COOR.sub.7, C.sub.3 -C.sub.6 alkenyl which is unsubstituted or substituted by halogen, C.sub.3 -C.sub.6 alkinyl which is unsubstituted or substituted by halogen, C.sub.4 -C.sub.7 cycloalkyl which is unsubstituted or substituted by halogen or methyl, an aryl or heterocyclic radical U having not more than 3 heteroatoms O, N and/or S, or a radical U which is linked via an alkylene bridge containing not more than 6 carbon atoms and up to 2 oxygen atoms; U is phenyl, phenoxyphenyl, biphenyl or 1- or 2-naphthyl, each of which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.4 alkoxy, or a saturated or unsaturated 5- to 7-membered heterocyclic radical T which is unsubstituted or substituted by one or more substituents from the group comprising halogen, C.sub.1 -C.sub.3 alkyl and/or C.sub.1 -C.sub.3 alkoxy; R.sub.5 and R.sub.6 independently of one another are hydrogen, C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.6 alkyl which is substituted by C.sub.1 -C.sub.3 alkoxy and/or cyano, or C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 alkinyl, C.sub.3 -C.sub.7 cycloalkyl, a radical U or a radical U which is linked via an alkylene bridge containing not more than 2 C atoms; or R.sub.5 and R.sub.6, together with the nitrogen atom, are a 5- to 7-membered heterocyclic radical W which is unsubstituted or substituted by methyl and has not more than 2 further heteroatoms O, N and/or S; R.sub.7 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sub.8 and R.sub.9 independently of one another are hydrogen, C.sub.1 -C.sub.6 alkyl, cyano, CONH.sub.2, CONHCONHR.sub.7, or phenyl which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkoxy; or, together with the connecting carbon atom, are also a 5- to 7-membered carbocyclic radical; and R.sub.10 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.5 -C.sub.7 cycloalkyl, phenyl or benzyl.
- 2. A compound of the formula I according to claim 1, in which: R.sub.1, R.sub.2 and R.sub.3 independently of one another are hydrogen, fluorine or methyl; A is --OR.sub.4, --SR.sub.4, --N(R.sub.5)R.sub.6, --N(R.sub.7)--N(R.sub.5)R.sub.6, --O--N.dbd.C(R.sub.8)R.sub.9, --N(R.sub.7)--OR.sub.10 ##STR54## R.sub.4 is C.sub.1 -C.sub.6 alkyl, C.sub.5 -C.sub.6 cycloalkyl, phenyl, benzyl, tetrahydrofuran-2-on-3-yl, 2-, 3- or 4-pyridyl, 2-, 4- or 5-pyrimidyl or (2,2-dimethyldioxolan-4-yl)-methyl; R.sub.5 and R.sub.6 independently of one another are hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.3 alkyl which is substituted by methoxy, ethoxy and/or cyano, or allyl, propargyl, C.sub.3 -C.sub.6 cycloalkyl, phenyl, benzyl, phenethyl, 2-furfurylmethyl, tetrahydrofuran-2-on-3-yl, 2,3- or 4-pyridyl, 2-,4- or 5-pyrimidyl, R.sub.7 is hydrogen, methyl or ethyl; or the group N(R.sub.5)R.sub.6 together forms a pyrrole, pyrrolidine, imidazol-1-yl, 1,2,4-triazol-1-yl, piperidine, morpholine or 2,6-dimethylmorpholine ring; R.sub.8 and R.sub.9 independently of one another are hydrogen, C.sub.1 -C.sub.6 alkyl, cyano, the radicals CONH.sub.2, CONHCONHR.sub.7 or phenyl, or, together with the connecting carbon atom, form a 5- to 7-membered carbocyclic radical; and R.sub.10 is hydrogen, C.sub.1 -C.sub.3 alkyl, allyl, C.sub.5 -C.sub.6 cycloalkyl, phenyl or benzyl.
- 3. A compound of the formula I according to claim 1, in which: R.sub.1, R.sub.2 and R.sub.3 independently of one another are hydrogen, fluorine or methyl; A is --OR.sub.4, --SR.sub.4, --N(R.sub.5)R.sub.6, --N(R.sub.7)--N(R.sub.5)R.sub.6, --O--N.dbd.C(R.sub.8)R.sub.9 or --N(R.sub.7)--OR.sub.10 ; R.sub.4 is C.sub.1 -C.sub.6 alkyl, C.sub.5 -C.sub.6 cycloalkyl, phenyl, benzyl, tetrahydrofuran-2-on-3-yl or 2-, 3- or 4-pyridyl; R.sub.5 and R.sub.6 independently of one another are hydrogen, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkyl which is substituted by methoxy and/or cyano, or allyl, propargyl, C.sub.3 -C.sub.5 cycloalkyl, phenyl, benzyl, 2-furfuryl, tetrahydrofuran-2-on-3-yl, 2-, 3- or 4-pyridyl, 2-, 4- or 5-pyrimidyl or piperidin-1-yl, or the group N(R.sub.5)R.sub.6 together is a pyrrolidine, imidazol-1-yl, piperidine, morpholine or 2,6-dimethylmorpholine ring; R.sub.7 is hydrogen, methyl or ethyl; R.sub.8 and R.sub.9 independently of one another are hydrogen, methyl, ethyl or the radicals cyano, CONH.sub.2, phenyl or benzyl, or, together with the connecting carbon atom, are cyclopentyl or cyclohexyl; and R.sub.10 is hydrogen, methyl, ethyl, allyl, C.sub.3 -C.sub.5 cycloalkyl or phenyl.
- 4. A compound of the formula I according to claim 1, in which: R.sub.1, R.sub.2 and R.sub.3 independently of one another are hydrogen or fluorine; A is --OR.sub.4, --SR.sub.4, --N(R.sub.5)R.sub.6 or --N(R.sub.7)--N(R.sub.5)R.sub.6 ; R.sub.4 is C.sub.1 -C.sub.4 alkyl, C.sub.5 -C.sub.6 cycloalkyl, phenyl, benzyl, 2-, 3- or 4-pyridyl or 2-, 4- or 5-pyrimidyl; R.sub.5 and R.sub.6 independently of one another are hydrogen, methyl, ethyl, allyl, propargyl, phenyl, benzyl, 2-furanylmethyl or 2-, 3- or 4-pyridyl, or the group N(R.sub.5)R.sub.6 together is a pyrrolidine, piperidine, morpholine, 2,6-dimethylmorpholine or imidazol-1-yl ring; and R.sub.7 is hydrogen, methyl or ethyl.
- 5. A compound of the formula I according to claim 1 from the group comprising:
- O-ethylbenzo-1,2,3-thiadiazole-7-thiocarboxylate (compound 1.2);
- S-methylbenzo-1,2,3-thiadiazole-7-thiocarboxylate (compound 1.6);
- benzo-1,2,3-thiadiazole-7-carboxylic acid thioamide (compound 2.1);
- 7-[benzo-1,2,3-thiadiazole]-N',N'-dimethylthiohydrazide (compound 3.1);
- S-ethylbenzo-1,2,3-thiadiazole-7-thiocarboxylate (compound 1.7);
- S-propylbenzo-1,2,3-thiadiazole-7-thiocarboxylate (compound 1.8);
- S-cyclopentylbenzo-1,2,3-thiadiazole-7-thiocarboxylate (compound 1.15);
- benzo-1,2,3-thiadiazole-7-thiocarboxylic acid morpholide (compound 2.15); and
- benzo-1,2,3-thiadiazole-7-thiocarboxylic acid piperidide (compound 2.43).
- 6. A compound of the formula III or a salt thereof with a hydrogen halide acid ##STR55## in which: R.sub.1, R.sub.2 and R.sub.3 independently of one another are hydrogen, halogen, methyl, methoxy or methylthio; R.sub.4 ' is C.sub.1 -C.sub.18 alkyl, C.sub.3 -C.sub.35 alkyl which is interrupted by an oxygen or sulfur atom, C.sub.1 -C.sub.8 alkyl which is substituted by halogen or --COOR.sub.7, C.sub.3 -C.sub.6 alkenyl which is unsubstituted or substituted by halogen, C.sub.3 -C.sub.6 alkinyl which is unsubstituted or substituted by halogen, C.sub.4 -C.sub.7 cycloalkyl which is unsubstituted or substituted by halogen or methyl, an aryl or heterocyclic radical U having not more than 3 heteroatoms O, N and/or S, or a radical U which is linked via an alkylene bridge containing not more than 6 carbon atoms and up to 2 oxygen atoms; U is phenyl, phenoxyphenyl, biphenyl or 1- or 2-naphthyl, each of which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.4 alkoxy, or a saturated or unsaturated 5- to 7-membered heterocyclic radical V which is unsubstituted or substituted by one or more substituents from the group comprising halogen, C.sub.1 -C.sub.3 alkyl and/or C.sub.1 -C.sub.3 alkoxy; and Hal is halogen.
- 7. A process for controlling phytopathogenic microorganisms, and increasing resistance to said microorganisms which comprises applying a microbicidally effective amount of a compound according to claim 1 to a plant or its location.
- 8. A process for controlling phytopathogenic microorganisms, and increasing resistance to said microorganisms which comprises applying a microbicidally effective amount of a compound according to claim 5 to a plant or its location.
- 9. A composition for controlling phytopathogenic microorganisms and increasing resistance to said microorganisms which comprises a carrier or other adjuvant and a microbicidally effective amount of a compound of claim 1.
- 10. A composition for controlling phytopathogenic microorganisms and increasing resistance to said microorganisms which comprises a carrier or other adjuvant and a microbicidally effective amount of a compound of claim 2.
- 11. A composition for controlling phytopathogenic microorganisms and increasing resistance to said microorganisms which comprises a carrier or other adjuvant and a microbicidally effective amount of a compound of claim 3.
- 12. A composition for controlling phytopathogenic microorganisms and increasing resistance to said microorganisms which comprises a carrier or other adjuvant and a microbicidally effective amount of a compound of claim 4.
- 13. A composition for controlling phytopathogenic microorganisms and increasing resistance to said microorganisms which comprises a carrier or other adjuvant and a microbicidally effective amount of a compound of claim 5.
- 14. A process for controlling phytopathogenic microorganisms, and increasing resistance to said microorganisms which comprises applying a microbicidally effective amount of a compound according to claim 2 to a plant or its location.
- 15. A process for controlling phytopathogenic microorganisms, and increasing resistance to said microorganisms which comprises applying a microbicidally effective amount of a compound according to claim 3 to a plant or its location.
- 16. A process for controlling phytopathogenic microorganisms, and increasing resistance to said microorganisms which comprises applying a microbicidally effective amount of a compound according to claim 4 to a plant or its location.
Priority Claims (2)
Number |
Date |
Country |
Kind |
3480/89 |
Sep 1989 |
CHX |
|
2483/90 |
Jul 1990 |
CHX |
|
Parent Case Info
This is a continuation of Ser. No. 07/586,095, filed Sep. 19, 1990, now abandoned.
US Referenced Citations (2)
Foreign Referenced Citations (2)
Number |
Date |
Country |
1695786 |
Apr 1971 |
DEX |
1176799 |
Jan 1970 |
GBX |
Non-Patent Literature Citations (1)
Entry |
P. Kirby et al., J. Chem Soc. (c) 2250-2253 (1970). |
Continuations (1)
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Number |
Date |
Country |
Parent |
586095 |
Sep 1990 |
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