Use of nitroethane derivatives as microbicides and specific...

Details Use of nitroethane derivatives as microbicides and specific... Use of nitroethane derivatives as microbicides and specific...

2000-06-13

2001-07-31

Trinh, Ba K. (Department: 1625)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C549S304000, C549S311000, C549S312000

Reexamination Certificate

active

06268514

ABSTRACT:

This application is a 371 of PCT/EP98/07815 dated Dec. 2, 1998.
The present invention relates to the use of nitroethane derivatives as microbicides, to specific novel nitroethane derivatives and to processes for their preparation.
Some of these nitroethane derivatives, such as, for example, the compound &agr;-L-xylo-3-hexulofuranosonic acid, 2-C-[2-nitro-1-phenylethyl], &ggr; lactone [CA-Reg. No. 175 433-01-09], the corresponding 4-chlorophenyl compound [CA-Reg. No. 175 433-02-0], 2,6-dichlorophenyl compound [CA-Reg. No. 175 433-03-01], 2-methoxyphenyl compound [CA-Reg. No. 175 433-04-02], 3-methoxyphenyl compound [CA-Reg. No. 175 433-05-03], 4-methoxyphenyl compound [CA-Reg. No. 175 433-06-04], 3-hydroxy-4-methoxyphenyl compound [CA-Reg. No. 175 433-07-05], and 4-methylphenyl compound [CA-Reg. No. 175 433-08-06], have already been disclosed. Hitherto, only the virostatic and cytostatic properties of these compounds have been investigated (see Pharmazie 51 (1996), 11-16).
A microbicidal activity of these compounds has hitherto not been disclosed.
We have found that nitroethane derivatives, some of which are known, of the formula I
where:
R
1
is hydrogen, C
1
-C
6
-alkyl which may be substituted by halogen, cyano, hydroxycarbonyl, C
1
-C
3
-alkoxy, C
1
-C
3
-alkylthio, C
1
-C
3
-alkoxycarbonyl, or is C
3
-C
6
-alkenyl, C
3
-C
6
-alkynyl, halogen, cyano or thiocyanato;
R
2
is hydrogen, formyl; halogen- or C
1
-C
3
-alkoxy-substituted or unsubstituted C
1
-C
6
-alkylcarbonyl, C
2
-C
6
-alkenylcarbonyl, C
4
-C
6
-alkyldienylcarbonyl or C
2
-C
6
-alkynylcarbonyl;
A is phenyl, naphthyl, quinolyl, quinazolyl, quinoxalyl, 1-methylindolyl, 1-methylbenzimidazolyl, 2-methylindazolyl, benzofuranyl, benzothienyl, benzoxazolyl, benzothiazolyl, which may carry a divalent substituent such as methylenedioxy, difluoromethylenedioxy, chlorofluoromethylenedioxy, dichloromethylenedioxy in adjacent positions or may in each case be mono- to pentasubstituted by halogen, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-haloalkylthio, amino, C
1
-C
4
-monoalkylamino, C
1
-C
4
-dialkylamino, C
3
-C
6
-cycloalkyl, C
1
-C
4
-alkoxycarbonyl, C
1
-C
4
-alkoxycarbonyl-C
1
-C
4
-alkyl, hydroxyl, nitro or cyano;
is furyl, thienyl, pyrrolyl, isoxazolyl, isothiazolyl, pyrazolyl, oxazolyl, thiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl or triazinyl, pyranyl or thiopyranyl which may in each case be mono- to trisubstituted by halogen, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-haloalkylthio, amino, C
1
-C
4
-monoalkylamino, C
1
-C
4
-dialkylamino, C
3
-C
6
-cycloalkyl, C
1
-C
4
-alkoxycarbonyl, C
1
-C
4
-alkoxycarbonyl-C
1
-C
4
-alkyl, hydroxyl, nitro or cyano;
have excellent microbicidal properties and can be used both in the protection of materials and in crop protection.
Particularly suitable for this use are compounds of the formula I in which
R
1
is hydrogen, C
1
-C
4
-alkyl which may be substituted by halogen, cyano, hydroxycarbonyl, C
1
-C
3
-alkoxy, C
1
-C
3
-alkylthio, C
1
-C
3
-alkoxycarbonyl, or is halogen and
R
2
is hydrogen.
Very particularly suitable are compounds of the formula I in which
R
1
is hydrogen or halogen;
R
2
is hydrogen and
A is phenyl, naphthyl, quinolyl, quinazolyl, quinoxalyl, benzofuranyl, benzothienyl, benzoxazolyl, benzothiazolyl, which may carry a divalent substituent such as methylenedioxy, difluoromethylenedioxy, chlorofluoromethylenedioxy in adjacent positions or may in each case be mono- to trisubstituted by halogen, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-haloalkylthio, C
1
-C
4
-alkoxycarbonyl, hydroxyl, nitro or cyano;
is furanyl, thienyl, pyrrolyl, isoxazolyl, isothiazolyl, pyrazolyl, oxazolyl, thiazolyl, imidazolyl, oxadiazolyl, pyridyl, pyranyl or thiopyranyl, each of which may be mono- to disubstituted by halogen, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-haloalkylthio, C
1
-C
4
-alkoxycarbonyl, nitro or cyano.
Depending on the substitution pattern, the compounds of the formula I may contain one or more chiral centers, in which case they are present as enantiomer or diastereomer mixtures. The invention provides both the use of the pure enantiomers or diastereomers and the use of the mixtures.
The present invention provides the novel nitroethane derivatives of the formula Ia
in which
R
1
is C
1
-C
6
-alkyl which may be substituted by halogen, cyano, hydroxycarbonyl, C
1
-C
3
-alkoxy, C
1
-C
3
-alkylthio, C
1
-C
3
-alkoxycarbonyl, or is C
3
-C
6
-alkenyl, C
3
-C
6
-alkynyl, halogen, cyano or thiocyanato and
R
2
is hydrogen, formyl; halogen- or C
1
-C
3
-alkoxy-substituted or unsubstituted C
1
-C
6
-alkylcarbonyl, C
2
-C
6
-alkenylcarbonyl, C
4
-C
6
-alkyldienylcarbonyl or C
2
-C
6
-alkynylcarbonyl;
or
R
1
is hydrogen, C
1
-C
6
-alkyl which may be substituted by halogen, cyano, hydroxycarbonyl, C
1
-C
3
-alkoxy, C
1
-C
3
-alkylthio, C
1
-C
3
-alkoxycarbonyl, or is C
3
-C
6
-alkenyl, C
3
-C
6
-alkynyl, halogen, cyano or thiocyanato and
R
2
is formyl; halogen- or C
1
-C
3
-alkoxy-substituted or unsubstituted C
1
-C
6
-alkylcarbonyl, C
2
-C
6
-alkenylcarbonyl, C
4
-C
6
-alkyldienylcarbonyl or C
2
-C
6
-alkynylcarbonyl;
and in each case
A is phenyl, naphthyl, quinolyl, quinazolyl, guinoxalyl, 1-methylindolyl, 1-methylbenzimidazolyl, 2-methylindazolyl, benzofuranyl, benzothienyl, benzoxazolyl, benzothiazolyl, which may carry a divalent substituent such as methylenedioxy, difluoromethylenedioxy, chlorofluoromethylenedioxy, dichloromethylenedioxy in adjacent positions or may in each case be mono- to pentasubstituted by halogen, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-haloalkylthio, amino, C
1
-C
4
-monoalkylamino, C
1
-C
4
-dialkylamino, C
3
-C
6
-cycloalkyl, C
1
-C
4
-alkoxycarbonyl, C
1
-C
4
-alkoxycarbonyl-C
1
-C
4
-alkyl, hydroxyl, nitro or cyano;
is furyl, thienyl, pyrrolyl, isoxazolyl, isothiazolyl, pyrazolyl, oxazolyl, thiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl or triazinyl, pyranyl or thiopyranyl, which are in each case mono- to trisubstituted by halogen, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-haloalkylthio, amino, C
1
-C
4
-monoalkylamino, C
1
-C
4
-dialkylamino, C
3
-C
6
-cycloalkyl, C
1
-C
4
-alkoxycarbonyl, C
1
-C
4
-alkoxycarbonyl-C
1
-C
4
-alkyl, hydroxyl, nitro or cyano.
The present invention furthermore provides the novel substituted nitroethane derivatives of the formula Ib
in which
R
1
is hydrogen, C
1
-C
6
-alkyl which may be substituted by halogen, cyano, hydroxycarbonyl, C
1
-C
3
-alkoxy, C
1
-C
3
-alkylthio, C
1
-C
3
-alkoxycarbonyl, or is C
3
-C
6
-alkenyl, C
3
-C
6
-alkynyl, halogen, cyano or thiocyanato;
R
2
is hydrogen, formyl; halogen- or C
1
-C
3
-alkoxy-substituted or unsubstituted C
1
-C
6
-alkylcarbonyl, C
2
-C
6
-alkenylcarbonyl, C
4
-C
6
-alkyldienylcarbonyl or C
2
-C
6
-alkynylcarbonyl and
A is phenyl, naphthyl, quinolyl, quinazolyl, quinoxalyl, 1-methylindolyl, 1-methylbenzimidazolyl, 2-methylindazolyl, benzofuranyl, benzothienyl, benzoxazolyl, benzothiazolyl, which may carry a divalent substituent such as methylenedioxy, difluoromethylenedioxy, chlorofluoromethylenedioxy, dichloromethylenedioxy in adjacent positions or may in each case be mono- to pentasubstituted by halogen, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-haloalkylthio, amino, C
1
-C
4
-monoalkylamino, C
1
-C
4
-dialkylamino, C
3
-C
6
-cycloalkyl, C
1
-C
4
-alkoxycarbonyl, C
1
-C
4
-alkoxycarbonyl-C
1
-C
4
-alkyl, hydroxyl, nitro or cyano;
is furyl, thienyl, pyrrolyl, isoxazolyl, isothiazolyl, pyr

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