Claims
- 1. A compound of the formula ##STR97## in which: X.sub.1, X.sub.2 and X.sub.3 independently of one another are hydrogen, methyl, methoxy, methylthio, halogen or nitro;
- A is C.sub.1 -C.sub.2 alkyl which is substituted by a minimum of 1 and a maximum of 3 X--C.sub.1 -C.sub.4 alkyl groups, methyl which is substituted by 2 or 3 halogen atoms, ethyl which is substituted by hydroxyl and/or not more than 4 halogen atoms, vinyl which is unsubstituted or substituted by not more than 3 halogen atoms; furthermore ethynyl, propargyl, formyl, acetyl, acetyl which is substituted by not more than 3 halogen atoms, or one of the groups C(R).dbd.N--N(R.sub.2)R.sub.3, C(N.dbd.N--U.sub.1).dbd.N--NH--U.sub.1, CH(R)--[N(R.sub.1)].sub.n --N(R.sub.2)R.sub.3, C(R)(CN)OR.sub.4, C(R).dbd.N(O).sub.n R.sub.3, CH(R)--O--N.dbd.C(R.sub.1)R.sub.2, CH(R)--O--N.dbd.C(CN)--CONH--R.sub.5, C(R.sub.6).dbd.N--(O).sub.n R, CH(R)--Y--E--R.sub.3, CO--[C(OR).sub.2 ].sub.n Q, C(Q).dbd.CH--OR or T--Q; in which furthermore:
- n is zero or 1;
- X and Y independently of one another are oxygen or sulfur;
- R and R.sub.1 independently of one another are hydrogen or C.sub.1 -C.sub.2 alkyl;
- R.sub.2 is hydrogen, C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 alkynyl, C.sub.3 -C.sub.7 cycloalkyl, benzyl or cyano;
- R.sub.3 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 alkynyl, C.sub.3 -C.sub.7 cycloalkyl, benzyl or is an aryl radical U;
- R.sub.4 is hydrogen, C.sub.1 -C.sub.6 alkyl, Si(C.sub.1 -C.sub.6 alkyl).sub.3 or OCOC.sub.1 -C.sub.3 alkyl;
- R.sub.5 is hydrogen or CONHR.sub.1 ;
- R.sub.6 is N(R.sub.1)R.sub.2, hydrazino or Q;
- E is CO or SO.sub.2 ;
- U and U.sub.1 independently of one another are a phenyl radical which is unsubstituted or monosubstituted or polysubstituted by identical or different substituents from the series comprising methyl, methoxy, halogen, trifluoromethyl, nitro or cyano;
- T is C.sub.1 -C.sub.2 alkylene, methylene which is substituted by amino, hydroxyl or halogen, the substituents being independent of one another, or is ethenylene which is unsubstituted or substituted by halogen or cyano;
- Q is COXR or cyano, with the exception of the following compounds:
- 7-formyl-1,2,3-benzothiadiazole;
- 7-acetyl-1,2,3-benzothiadiazole;
- 6-chloro-7-formyl-1,2,3-benzothiadiazole;
- 6-methylthio-7-formyl-1,2,3-benzothiadiazole;
- 4-bromo-6-chloro-7-formyl-1,2,3-benzothiadiazole;
- 6-methoxy-7-formyl-1,2,3-benzothiadiazole;
- 7-hydroxyiminomethyl-1,2,3-benzothiadiazole;
- 6-methoxy-7-hydroxyiminomethyl-1,2,3-benzothiadiazole,
- 7-dibromoacetyl-1,2,3-benzothiadiazole.
- 2. A compound of the formula I ##STR98## in which: X.sub.1, X.sub.2 and X.sub.3 independently of one another are hydrogen or fluorine;
- A is C.sub.1 -C.sub.2 alkyl which is substituted by a minimum of 1 and a maximum of 3 X--C.sub.1 -C.sub.4 alkyl groups, methyl which is substituted by 2 or 3 halogen atoms, ethyl which is substituted by hydroxyl and/or not more than 4 halogen atoms, or formyl, acetyl, or one of the groups C(R).dbd.N--N(R.sub.2)R.sub.3, CH(R)--[N(R.sub.1)].sub.n --N(R.sub.2)R.sub.3, C(R)(CN)OR.sub.4, C(R).dbd.N(O).sub.n R.sub.3, CH(R)--O--N.dbd.C(R.sub.1)R.sub.2, CH(R)--O--N.dbd.C(CN)--CONH--R.sub.5, C(R.sub.6).dbd.N--(O).sub.n R, CH(R)--Y--E--R.sub.3, CO--[C(OR).sub.2 ].sub.n COXR, C(Q).dbd.CH--OR or T--Q; in which furthermore:
- n is zero or 1;
- X and Y are oxygen;
- R and R.sub.1 independently of one another are hydrogen or C.sub.1 -C.sub.2 alkyl;
- R.sub.2 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, C.sub.3 -C.sub.6 cycloalkyl or benzyl;
- R.sub.3 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, C.sub.3 -C.sub.6 cycloalkyl or a phenyl radical which is substituted by identical or different substituents from the series comprising methyl, halogen or trifluoromethyl;
- R.sub.4 is hydrogen, C.sub.1 -C.sub.3 alkyl or Si(C.sub.1 -C.sub.2 alkyl).sub.3 ;
- R.sub.5 is hydrogen or CONHC.sub.1 -C.sub.3 alkyl;
- R.sub.6 is amino or cyano;
- E is CO;
- T is methylene, methylene which is substituted by amino or ethenylene;
- Q is COOR or cyano, with the exception of the following compounds:
- 7-formyl-1,2,3-benzothiadiazole;
- 7-acetyl-1,2,3-benzothiadiazole;
- 6-chloro-7-formyl-1,2,3-benzothiadiazole;
- 6-methylthio-7-formyl-1,2,3-benzothiadiazole;
- 4-bromo-6-chloro-7-formyl-1,2,3-benzothiadiazole;
- 6-methoxy-7-formyl-1,2,3-benzothiadiazole;
- 7-hydroxyiminomethyl-1,2,3-benzothiadiazole;
- 6-methoxy-7-hydroxyiminomethyl-1,2,3-benzothiadiazole,
- 7-dibromoacetyl-1,2,3-benzothiadiazole.
- 3. A compound of the formula I ##STR99## in which: X.sub.1, X.sub.2 and X.sub.3 are hydrogen;
- A is methyl which is substituted by a minimum of 1 and a maximum of 2 X--C.sub.1 -C.sub.4 alkyl groups, methyl which is substituted by 2 or 3 fluorine or chlorine atoms, ethyl which is substituted by hydroxyl or chlorine, or formyl, acetyl, or one of the groups C(R).dbd.N--N(R.sub.2)R.sub.3, CH(R)--[N(R.sub.1)].sub.n --N(R.sub.2)R.sub.3, C(R)(CN)OR.sub.4, C(R).dbd.N(O).sub.n R.sub.3, CH(R)--O--N.dbd.C(R.sub.1)R.sub.2, CH(R)--O--N.dbd.C(CN)--CONHR.sub.5, C(R.sub.6).dbd.N--OR, CH(R)--Y--E----R.sub.3, CO[C(OR).sub.2 ].sub.n COXR, C(COOR).dbd.CH--OR or T--Q; in which furthermore:
- n is 1;
- X is oxygen;
- R and R.sub.1 independently of one another are hydrogen or methyl;
- R.sub.2 is hydrogen, C.sub.1 -C.sub.2 alkyl, allyl, propargyl, cyclopropyl or benzyl;
- R.sub.3 is hydrogen, C.sub.1 -C.sub.2 alkyl, allyl, propargyl, cyclopropyl, or a phenyl radical which is substituted by identical or different substituents from the series comprising methyl, fluorine, chlorine or trifluoromethyl;
- R.sub.4 is hydrogen, C.sub.1 -C.sub.2 alkyl or Si(CH.sub.3).sub.3 ;
- R.sub.5 is hydrogen or CONH-C.sub.1 -C.sub.2 alkyl;
- R.sub.6 is amino;
- Y is oxygen;
- E is CO;
- T is methylene or cyano, with the exception of the following compounds:
- 7-formyl-1,2,3-benzothiadiazole;
- 7-acetyl-1,2,3-benzothiadiazole;
- 6-chloro-7-formyl-1,2,3-benzothiadiazole;
- 6-methylthio-7-formyl-1,2,3-benzothiadiazole;
- 4-bromo-6-chloro-7-formyl-1,2,3-benzothiadiazole;
- 6-methoxy-7-formyl-1,2,3-benzothiadiazole;
- 7-hydroxyiminomethyl-1,2,3-benzothiadiazole;
- 6-methoxy-7-hydroxyiminomethyl-1,2,3-benzothiadiazole,
- 7-dibromoacetyl-1,2,3-benzothiadiazole.
- 4. A compound of the formula I ##STR100## in which: X.sub.1, X.sub.2 and X.sub.3 are hydrogen;
- A is methyl which is substituted by a minimum of 1 and a maximum of 2 X--C.sub.1 -C.sub.2 alkyl groups, methyl which is substituted by 2 or 3 fluorine atoms, ethyl which is substituted by hydroxyl or chlorine, or formyl, or one of the groups C(R).dbd.N--N(R.sub.2)R.sub.3, CH(R)--[N(R.sub.1)].sub.n --N(R.sub.2)R.sub.3, C(R)(CN)OR.sub.4, C(R).dbd.N--R.sub.3, CH(R)--O--N.dbd.C(R.sub.1)R.sub.2, C(R.sub.6).dbd.N--OR, CH(R)--Z--E--R.sub.3, CO[C(OR).sub.2 ].sub.n COXR or T--Q; in which furthermore:
- n is 1;
- X is oxygen;
- R and R.sub.1 independently of one another are hydrogen or methyl;
- R.sub.2 is hydrogen, methyl, allyl, cyclopropyl or benzyl;
- R.sub.3 is hydrogen, methyl, allyl, cyclopropyl, or a phenyl radical which is substituted by identical or different substituents from the series comprising methyl, fluorine, chlorine or trifluoromethyl;
- R.sub.4 is hydrogen, methyl or Si(CH.sub.3).sub.3 ;
- R.sub.5 is hydrogen or CONH--CH.sub.2 --CH.sub.3 ;
- R.sub.6 is amino;
- Y is oxygen;
- E is CO;
- T is methylene;
- Q is COOCH.sub.3 or cyano, with the exception of the following compounds:
- 7-formyl-1,2,3-benzothiadiazole;
- 7-acetyl-1,2,3-benzothiadiazole;
- 6-chloro-7-formyl-1,2,3-benzothiadiazole;
- 6-methylthio-7-formyl-1,2,3-benzothiadiazole;
- 4-bromo-6-chloro-7-formyl-1,2,3-benzothiadiazole;
- 6-methoxy-7-formyl-1,2,3-benzothiadiazole;
- 7-hydroxyiminomethyl-1,2,3-benzothiadiazole;
- 6-methoxy-7-hydroxyiminomethyl-1,2,3-benzothiadiazole,
- 7-dibromoacetyl-1,2,3-benzothiadiazole.
- 5. A compound of the formula ##STR101## selected from the group: 7-acetoxymethyl-1,2,3-benzothiadiazole;
- 7-[2-cyanoacetamidyl0iminooxymethyl]-1,2,3-benzothiadiazole;
- 7-(N-methoxyiminomethyl)-1,2,3-benzothiadiazole;
- 7-(N-methoxyiminohydroxymethyl)-1,2,3-benzothiadiazole;
- 7-methoxymethyl-1,2,3-benzothiadiazole;
- 3-(7-benzo-1,2,3-thiadiazolyl)acrylic acid;
- 7-cyanomethyl-1,2,3-benzothiadiazole;
- 7-trichloromethyl-1,2,3-benzothiadiazole;
- 7-dichloromethyl-1,2,3-benzothiadiazole;
- benzo-1,2,3-thiadiazole-7-(N-hydroxycarboximide-amide);
- benzo-1,2,3-thiadiazole-7-(N-methoxyhydroxamic acid);
- 2-(benzo-1,2,3-thiadiazolyl)-2-hydroxyiminoacetonitrile;
- 5-fluoro-benzo-1,2,3-thiadiazole-7-carbaldehyde;
- 6-fluoro-benzo-1,2,3-thiadiazole-7-carbaldehyde;
- 4-fluoro-benzo-1,2,3-thiadiazole-7-carbaldehyde;
- N,N-diphenyl-C-[benzo-1,2,3-thiadiazol-7'yl]formazan;
- 7-(bromoacetyl)benzo-1,2,3-thiadiazole.
Priority Claims (1)
Number |
Date |
Country |
Kind |
666/91 |
Mar 1991 |
CHX |
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Parent Case Info
This application is a continuation of application Ser. No. 841,676, filed Feb. 26, 1992, now abandoned.
US Referenced Citations (3)
Number |
Name |
Date |
Kind |
4931581 |
Schurter et al. |
Jun 1990 |
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5051436 |
Kunz et al. |
Sep 1991 |
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5066661 |
Kunz et al. |
Nov 1991 |
|
Foreign Referenced Citations (2)
Number |
Date |
Country |
1695786 |
Apr 1971 |
DEX |
1176799 |
Jan 1970 |
GBX |
Non-Patent Literature Citations (6)
Entry |
Clarke et al., Chemical Abstracts (1980) 220643x. |
J. Chem. Research(s), p. 197 (1980). |
J. Chem. Soc. 1970 pp. 2250-2253. |
J. Chem. Soc. 1971 pp. 3997-3999. |
J. Chem. Res. 1980 pp. 190-191. |
J. Chem. Res. 1980 pp. 2845-2866. |
Continuations (1)
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Number |
Date |
Country |
Parent |
841676 |
Feb 1992 |
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