Claims
- 1. A compound of formula I ##STR18## wherein: R.sub.1 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy having at least two identical or different halogen atoms, CF.sub.3, nitro or the group N(R')R", wherein R' and R" are each independently of the other C.sub.1 -C.sub.4 alkyl;
- R.sub.2 is phenoxy or phenylthio each of which is unsubstituted or mono-to tri-substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy having at least two identical or different halogen atoms, cyano, nitro, C.sub.2 -C.sub.4 alkenyl, C.sub.2 -C.sub.4 alkynyl, phenyl, 2-phenylethynyl or by a further phenoxy radical that is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl and/or by C.sub.1 -C.sub.4 alkoxy; or R.sub.2 is phenoxy which is substituted in the 3 and 4 positions by the radical --O--CH.sub.2 --O--;
- R.sub.3 is alkyl, aryl or aralkyl having a maximum of 14 carbon atoms, these radicals can be substituted by halogen, C.sub.1 -C.sub.4 alkyl and/or by nitro.
- 2. A compound according to claim 1 of formula I wherein: R.sub.1 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, methoxy, ethoxy, CF.sub.3, NO.sub.2, C.sub.1 -C.sub.2 haloalkoxy having at least two fluorine atoms, diethylamine or dimethylamine; and R.sub.2 and R.sub.3 are as defined for formula I.
- 3. A compound according to claim 2 of formula I wherein: R.sub.1 is hydrogen, fluorine, chlorine, bromine, methyl, ethyl, methoxy, CF.sub.3, NO.sub.2, C.sub.1 -C.sub.2 haloalkoxy having at least 2 fluorine atoms, or dimethylamine; and R.sub.2 and R.sub.3 are as defined for formula I.
- 4. A compound according to claim 3 of formula I wherein: R.sub.1 is hydrogen, chlorine, bromine, methyl, methoxy, CF.sub.3, NO.sub.2, trifluoromethoxy, trifluorochloroethoxy, difluoromethoxy or dimethylamine; and R.sub.2 and R.sub.3 are as defined for formula I.
- 5. A compound according to claim 4 of formula I wherein: R1 is chlorine, methyl, methoxy, CF.sub.3 or dimethylamine; and R.sub.2 and R.sub.3 are as defined for formula I.
- 6. A compound according to claim 1 of formula I wherein: R.sub.2 is phenoxy or phenylthio each of which is unsubstituted or mono- or di-substituted by fluorine, chlorine, bromine, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.2 haloalkoxy having at least 2 fluorine atoms, nitro, cyano, allyl, propargyl, 2-phenylethynyl or by a further phenoxy radical that is unsubstituted or substituted by fluorine, chlorine, bromine or by methyl; and R.sub.1 and R.sub.3 are as defined for formula I.
- 7. A compound according to claim 6 of formula I wherein: R.sub.2 is phenoxy that is unsubstituted or substituted by fluorine, chlorine, bromine, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.2 haloalkoxy having at least 2 fluorine atoms, cyano, nitro, allyl, propargyl, 2-phenylethynyl or by a further phenoxy radical that is unsubstituted or substituted by fluorine, chlorine, bromine or by methyl; and R.sub.1 and R.sub.3 are as defined for formula I.
- 8. A compound according to claim 7 of formula I wherein: R.sub.2 is phenylthio that is unsubstituted or substituted by fluorine, chlorine, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 haloalkoxy having at least 2 fluorine atoms, nitro, allyl, propargyl or by 2-phenylethynyl; and R.sub.1 and R.sub.3 are as defined for formula I.
- 9. A compound according to claim 8 of formula I wherein: R.sub.2 is phenoxy that is unsubstituted or substituted by chlorine, bromine, methyl, tert-butyl, methoxy, ethoxy, trifluoromethoxy, cyano, nitro, allyl, propargyl, 2-phenylethynyl or by a further phenoxy radical that is unsubstituted or substituted by fluorine, bromine or by methyl; and R.sub.1 and R.sub.3 are as defined for formula I.
- 10. A compound according to claim 1 of formula I wherein: R.sub.3 is C.sub.1 -C.sub.4 alkyl; C.sub.1 -C.sub.4 alkyl substituted by halogen; phenyl; phenyl substituted by halogen, C.sub.1 -C.sub.4 alkyl and/or by nitro; benzyl; or benzyl substituted by halogen, C.sub.1 -C.sub.4 alkyl and/or by nitro; and R.sub.1 and R.sub.2 are as defined for formula I.
- 11. A compound according to claim 10 of formula I wherein: R.sub.3 is C.sub.1 -C.sub.4 alkyl; C.sub.1 -C.sub.4 alkyl substituted by fluorine or by chlorine; phenyl; phenyl substituted by chlorine, methyl or by nitro; benzyl; or benzyl substituted by chlorine, methyl or by nitro; and R.sub.1 and R.sub.2 are as defined for formula I.
- 12. A compound according to claim 1 of formula I wherein: R.sub.1 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, methoxy, ethoxy, CF.sub.3, NO.sub.2, C.sub.1 -C.sub.2 haloalkoxy having at least 2 fluorine and/or 2 chlorine atoms, diethylamine or dimethylamine;
- R.sub.2 is phenoxy or phenylthio each of which is unsubstituted or mono-or di-substituted by fluorine, chlorine, bromine, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.2 haloalkoxy having at least 2 fluorine atoms, cyano, nitro, allyl, propargyl, 2-phenylethynyl or by a further phenoxy radical that is unsubstituted or substituted by fluorine, chlorine, bromine or by methyl; and
- R.sub.3 is C.sub.1 -C.sub.4 alkyl; C.sub.1 -C.sub.4 alkyl substituted by halogen; phenyl; phenyl substituted by halogen, C.sub.1 -C.sub.4 alkyl and/or by nitro; benzyl; or benzyl substituted by halogen, C.sub.1 -C.sub.4 alkyl and/or by nitro.
- 13. A compound according to claim 12 of formula I wherein: R.sub.1 is hydrogen, fluorine, chlorine, bromine, methyl, ethyl, methoxy, CF.sub.3, NO.sub.2, C.sub.1 -C.sub.2 haloalkoxy having at least 2 fluorine atoms, or dimethylamine;
- R.sub.2 is phenoxy that is unsubstituted or substituted by fluorine, chlorine, bromine, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.2 haloalkoxy having at least 2 fluorine atoms, cyano, nitro, allyl, propargyl, 2-phenylethynyl or by a further phenoxy radical that is unsubstituted or substituted by fluorine, bromine or by methyl; and
- R.sub.3 is C.sub.1 -C.sub.4 alkyl; C.sub.1 -C.sub.4 alkyl substututed by fluorine or by chlorine; phenyl; phenyl substituted by chlorine, methyl or by nitro; benzyl; or benzyl substituted by chlorine, methyl or by nitro.
- 14. A compound according to claim 13 of formula I wherein: R.sub.1 is hydrogen, chlorine, bromine, methyl, methoxy, CF.sub.3, NO.sub.2, trifluoromethoxy, trifluorochloroethoxy, difluoromethoxy or dimethylamine;
- R.sub.2 is phenylthio that is unsubstituted or substituted by fluorine, chlorine, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 haloalkoxy having at least 2 fluorine atoms, nitro, allyl, propargyl or by 2-phenylethynyl; and
- R.sub.3 is C.sub.1 -C.sub.4 alkyl; C.sub.1 -C.sub.4 alkyl substituted by fluorine or by chlorine; phenyl; phenyl substituted by chlorine, methyl or by nitro; benzyl; or benzyl substituted by chlorine, methyl or by nitro.
- 15. A compound according to claim 14 of formula I wherein: R.sub.1 is chlorine, methyl, methoxy, CF.sub.3 or dimethylamine;
- R.sub.2 is phenoxy that is unsubstituted or substituted by chlorine, bromine, methyl, tert-butyl, methoxy, ethoxy, trifluoromethoxy, cyano, nitro, allyl, propargyl, 2-phenylethynyl or by a further phenoxy radical that is unsubstituted or substituted by fluorine, bromine or by methyl; and
- R.sub.3 is C.sub.1 -C.sub.4 alkyl; C.sub.1 -C.sub.4 alkyl substituted by fluorine or by chlorine; phenyl; phenyl substituted by chlorine, methyl or by nitro; benzyl; or benzyl substituted by chlorine, methyl or by nitro.
- 16. A compound of formula I according to claim 1 selected from the group consisting of:
- 1-N-methanesulfonyl-5-chloro-6-phenoxy-benzotriazole;
- 1-N-methanesulfonyl-5-chloro-6-(2-chlorophenoxy)-benzotriazole;
- 1-N-methanesulfonyl-5-chloro-6-(4-chlorophenoxy)-benzotriazole;
- 1-N-methanesulfonyl-5-chloro-6-(2,4-dibromophenoxy)-benzotriazole;
- 1-N-methanesulfonyl-5-chloro-6-(2-fluorophenoxy)-benzotriazole;
- 1-N-methanesulfonyl-5-chloro-6-(4-ethoxyphenoxy)-benzotriazole;
- 3-N-methanesulfonyl-5-chloro-6-phenoxy-benzotriazole;
- 3-N-methanesulfonyl-5-chloro-6-(2-chlorophenoxy)-benzotriazole;
- 3-N-methanesulfonyl-5-chloro-6-(4-chlorophenoxy)-benzotriazole;
- 3-N-methanesulfonyl-5-chloro-6-(2,4-dibromophenoxy)-benzotriazole;
- 3-N-methanesulfonyl-5-chloro-6-(2-fluorophenoxy)-benzotriazole; and
- 3-N-methanesulfonyl-5-chloro-6-(4-ethoxyphenoxy)-benzotriazole;
- and mixtures of the 1-N- and 3-N-substituted structural isomers.
- 17. A composition for controlling or preventing an attack by harmful microorganisms, which comprises a microbicidally effective amount of a compound or mixture of compounds of formula I ##STR19## wherein: R.sub.1 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy having at least two identical or different halogen atoms, CF.sub.3, nitro or the group N(R')R", wherein R' and R" are each independently of the other C.sub.1 -C.sub.4 alkyl;
- R.sub.2 is phenoxy or phenylthio each of which is unsubstituted or mono-to tri-substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy having at least two identical or different halogen atoms. cyano, nitro, C.sub.2 -C.sub.4 alkenyl, C.sub.2 -C.sub.4 alkynyl, phenyl, 2-phenylethynyl or by a further phenoxy radical that is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl and/or by C.sub.1 -C.sub.4 alkoxy; or R.sub.2 is phenoxy which is substituted in the 3 and 4 positions by the radical --O--CH.sub.2 --O--;
- R.sub.3 is alkyl, aryl or aralkyl having a maximum of 14 carbon atoms, these radicals can be substituted by halogen, C.sub.1 -C.sub.4 alkyl and/or by nitro;
- together with a suitable carrier.
- 18. A composition of claim 17 wherein R.sub.1 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, methoxy, ethoxy, CF.sub.3, NO.sub.2, C.sub.1 -C.sub.2 haloalkoxy having at least two fluorine atoms, diethylamine or dimethylamine.
- 19. A composition of claim 17 wherein
- R.sub.1 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, methoxy, ethoxy, CF.sub.3, NO.sub.2, C.sub.1 -C.sub.2 haloalkoxy having at least 2 fluorine and/or 2 chlorine atoms, diethylamine or dimethylamine;
- R.sub.2 is phenoxy or phenylthio each of which is unsubstituted or mono-or di-substituted by fluorine, chlorine, bromine, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.2 haloalkoxy having at least 2 fluorine atoms, cyano, nitro, allyl, propargyl, 2-phenylethynyl or by a further phenoxy radical that is unsubstituted or substituted by fluorine, chlorine, bromine or by methyl; and R.sub.3 is C.sub.1 -C.sub.4 alkyl; C.sub.1 -C.sub.4 alkyl substituted by halogen; phenyl; phenyl substituted by halogen, C.sub.1 -C.sub.4 alkyl and/or by nitro; benzyl; or benzyl substituted by halogen, C.sub.1 -C.sub.4 alkyl and/or by nitro.
- 20. A composition of claim 17 wherein the compound of formula I is selected from the group consisting of
- 1-N-methanesulfonyl-5-chloro-6-phenoxy-benzotriazole;
- 1-N-methanesulfonyl-5-chloro-6-(2-chlorophenoxy)-benzotriazole;
- 1-N-methanesulfonyl-5-chloro-6-(4-chlorophenoxy)-benzotriazole;
- 1-N-methanesulfonyl-5-chloro-6-(2,4-dibromophenoxy)-benzotriazole;
- 1-N-methanesulfonyl-5-chloro-6-(2-fluorophenoxy)-benzotriazole;
- 1-N-methanesulfonyl-5-chloro-6-(4-ethoxyphenoxy)-benzotriazole;
- 3-N-methanesulfonyl-5-chloro-6-phenoxy-benzotriazole;
- 3-N-methanesulfonyl-5-chloro-6-(2-chlorophenoxy)-benzotriazole;
- 3-N-methanesulfonyl-5-chloro-6-(4-chlorophenoxy)-benzotriazole;
- 3-N-methanesulfonyl-5-chloro-6-(2,4-dibromophenoxy)-benzotriazole;
- 3-N-methanesulfonyl-5-chloro-6-(2-fluorophenoxy)-benzotriazole; and
- 3-N-methanesulfonyl-5-chloro-6-(4-ethoxyphenoxy)-benzotriazole;
- and mixtures of the 1-N- and 3-N-substituted structural isomers.
- 21. A method of controlling or preventing an attack on cultivated plants by phytopathogenic microorganisms, which comprises applying to the plants, parts of plants or the locus thereof, a microbicidally effective amount of a compound or mixture of compounds of formula I ##STR20## wherein: R.sub.1 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy having at least two identical or different halogen atoms, CF.sub.3, nitro or the group N(R')R", wherein R' and R" are each independently of the other C.sub.1 -C.sub.4 alkyl;
- R.sub.2 is phenoxy or phenylthio each of which is unsubstituted or mono- to tri-substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy having at least two identical or different halogen atoms, cyano, nitro, C.sub.2 -C.sub.4 alkenyl, C.sub.2 -C.sub.4 alkynyl, phenyl, 2-phenylethynyl or by a further phenoxy radical that is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl and/or by C.sub.1 -C.sub.4 alkoxy; or R.sub.2 is phenoxy which is substituted in the 3 and 4 positions by the radical --O--CH.sub.2 --O--;
- R.sub.3 is alkyl, aryl or aralkyl having a maximum of 14 carbon atoms, these radicals can be substituted by halogen, C.sub.1 -C.sub.4 alkyl and/or by nitro.
- 22. A method of claim 21 wherein R.sub.1 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, methoxy, ethoxy, CF.sub.3, NO.sub.2, C.sub.1 -C.sub.2 haloalkoxy having at least two fluorine atoms, diethylamine or dimethylamine.
- 23. A method according to claim 21, wherein phytopathogenic fungi are controlled.
- 24. A method according to claim 21, wherein the phytopathogenic fungi are Oomycetes.
- 25. A method according to claim 24, wherein the Oomycetes are the species Plasmopara and Phytophthora.
Priority Claims (1)
Number |
Date |
Country |
Kind |
2065/90 |
Jun 1990 |
CHX |
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Parent Case Info
This application is a divisional of Ser. No. 07/931,884, filed Aug. 18, 1992, now abandoned, which is a continuation of Ser. No. 07/717,751, filed Jun. 19, 1991, now abandoned.
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2943017 |
Sasse et al. |
Jun 1960 |
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4622323 |
Giraudeu et al. |
Nov 1986 |
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4734427 |
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178708 |
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EPX |
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DEX |
Non-Patent Literature Citations (1)
Entry |
Chem. Abst. 114:6515r-Barton (1991). |
Divisions (1)
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Number |
Date |
Country |
Parent |
931884 |
Aug 1992 |
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Continuations (1)
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Number |
Date |
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Parent |
717751 |
Jun 1991 |
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