DE4428380A1 - 4-trifluoromethylbenzamide - Google Patents

Abstract

The invention pertains to novel 4-trifluoromethylbenzamides of formula (I), a method for their preparation and their use as pesticides in plant protection and materials protection.

Description

The invention relates to new 4-trifluoromethylbenzamides, a process for their Production and their use as pesticides in crop protection and in material protection.

It is known that certain 4-trifluoromethylbenzamides, such as that Compounds 2-hydroxy-4-trifluoromethyl-N- (3-chloro- or 3-bromo- or 3-methyl- or 4-ethyl or 4-isopropyl or 3,4-dimethyl or 3,5-dichloro or 3-chloro, 4- methyl-phenyl) -benzamide possess fungicidal properties (see, for example, WO-A 92/17066).

The effectiveness of these previously known compounds is, however, in particular low application rates are not completely satisfactory in all areas of application.

There were new 4-trifluoromethylbenzamides of the formula (I)

in which
Ar represents substituted phenyl,
except for the meanings:
3-chlorophenyl; 3-bromophenyl; 3-methylphenyl; 3-trifluoromethylphenyl; 4-chlorophenyl; 4-methoxyphenyl; 4-trifluoromethylphenyl; 4- (C₁-C₃) alkyl phenyl; 3,5-dichlorophenyl; 3-chloro-4-methylphenyl and 3,4-dimethylphenyl;
found.

It was also found that the new 4-trifluoromethylbenzamides of the formula (I)

in which
Ar has the meaning given above,
obtained when 2-hydroxy-4-trifluoromethylbenzoic acid or its ester of the formula (II) is obtained,

in which
R represents hydrogen or alkyl,
with anilines of the formula (III),

H₂N-Ar (III)

in which
Ar has the meaning given above,
in the presence of a condensing agent and optionally in the presence of a diluent and a reaction auxiliary.

Finally, it was found that the new 4-trifluoromethylbenzamides of the formula (I) are very suitable as pesticides. You stand out in particular through strong microbicidal properties both in crop protection and also in material protection and high insecticidal and acaricidal effectiveness.

Surprisingly, the 4-trifluoromethylbenzamides according to the invention show the Formula (I) has better efficacy than the most constitutionally similar previously known Links.

The 4-trifluoromethylbenzamides according to the invention are represented by the formula (I) generally defined.

The following groups of substances (a) to (g) of the formulas (Ia) to (Ig) are preferred:

in which
R1 is halogen, cyano, nitro; each straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 6 carbon atoms; each straight-chain or branched haloalkyl, haloalkoxy or haloalkylthio each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms;
each straight-chain or branched alkoxycarbonyl or alkoximino alkyl each having 1 to 4 carbon atoms in the individual alkyl parts; Amino, aminocarbonyl; in each case straight-chain or branched alkyl amino, alkylaminocarbonyl, dialkylamino or dialkylaminocarbonyl each having 1 to 4 carbon atoms in the individual alkyl parts; each straight-chain or branched alkenyl, alkenyloxy or alkenylthio each having 2 to 4 carbon atoms; and optionally optionally up to three times, identical or different phenyl substituted by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms.

in which
R² for fluorine, iodine, cyano, nitro; straight-chain or branched alkyl having 2 to 6 carbon atoms; each straight-chain or branched alkoxy or alkylthio each having 1 to 6 carbon atoms; straight-chain or branched haloalkyl having 2 to 4 carbon atoms and 1 to 9 identical or different halogen atoms; each straight-chain or branched haloalkoxy or haloalkylthio each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms;
each straight-chain or branched alkoxycarbonyl or alkoximino alkyl each having 1 to 4 carbon atoms in the individual alkyl parts; Amino, aminocarbonyl; in each case straight-chain or branched alkyl amino, alkylaminocarbonyl, dialkylamino or dialkylaminocarbonyl each having 1 to 4 carbon atoms in the individual alkyl parts; each straight-chain or branched alkenyl, alkenyloxy or alkenylthio each having 2 to 4 carbon atoms; and optionally phenyl which is monosubstituted to trisubstituted, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms.

in which
R⁴ for fluorine, bromine, iodine, cyano, nitro; straight-chain or branched alkyl having 4 to 6 carbon atoms; straight-chain or branched alkoxy with 2 to 6 carbon atoms; straight-chain or branched alkylthio having 1 to 6 carbon atoms; straight-chain or branched haloalkyl having 2 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, straight-chain or branched haloalkoxy or haloalkylthio each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms;
each straight-chain or branched alkoxycarbonyl or alkoximino alkyl each having 1 to 4 carbon atoms in the individual alkyl parts; Amino, aminocarbonyl; in each case straight-chain or branched alkyl amino, alkylaminocarbonyl, dialkylamino or dialkylaminocarbonyl each having 1 to 4 carbon atoms in the individual alkyl parts; each straight-chain or branched alkenyl, alkenyloxy or alkenylthio each having 2 to 4 carbon atoms; and optionally phenyl which is monosubstituted to trisubstituted, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms.

in which
Ar¹ for the groupings

stands,
wherein R¹, R², R³ and R⁴ are the same or different and are halogen, cyano, nitro; each straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 6 carbon atoms; each straight-chain or branched haloalkyl, haloalkoxy or haloalkylthio each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms;
each straight-chain or branched alkoxycarbonyl or alkoximino alkyl each having 1 to 4 carbon atoms in the individual alkyl parts; Amino, aminocarbonyl; in each case straight-chain or branched alkyl amino, alkylaminocarbonyl, dialkylamino or dialkylaminocarbonyl each having 1 to 4 carbon atoms in the individual alkyl parts; each straight-chain or branched alkenyl, alkenyloxy or alkenylthio each having 2 to 4 carbon atoms; and optionally optionally up to three times, identical or different, substituted by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms;
or R¹ and R² together represent in each case straight-chain or branched alkylenedioxo or haloalkylenedioxo each having 1 to 4 carbon atoms and 1 to 8 identical or different halogen atoms.

in which
R² for halogen, cyano, nitro; each straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 6 carbon atoms; each straight-chain or branched haloalkyl, haloalkoxy or haloalkylthio each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms;
each straight-chain or branched alkoxycarbonyl or alkoximino alkyl each having 1 to 4 carbon atoms in the individual alkyl parts; Amino, aminocarbonyl; in each case straight-chain or branched alkyl amino, alkylaminocarbonyl, dialkylamino or dialkylaminocarbonyl each having 1 to 4 carbon atoms in the individual alkyl parts; each straight-chain or branched alkenyl, alkenyloxy or alkenylthio each having 2 to 4 carbon atoms; and optionally phenyl which is monosubstituted to trisubstituted, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and
R³ for fluorine, bromine, iodine, cyano, nitro; each straight-chain or branched alkyl, alkoxy or aklylthio each having 1 to 6 carbon atoms; each straight-chain or branched haloalkyl; Haloalkoxy or haloalkylthio each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms;
each straight-chain or branched alkoxycarbonyl or alkoximino alkyl each having 1 to 4 carbon atoms in the individual alkyl parts; Amino, aminocarbonyl; in each case straight-chain or branched alkyl amino, alkylaminocarbonyl, dialkylamino or dialkylaminocarbonyl each having 1 to 4 carbon atoms in the individual alkyl parts; each straight-chain or branched alkenyl, alkenyloxy or alkenylthio each having 2 to 4 carbon atoms; and optionally optionally up to three times, identical or different phenyl substituted by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms.

in which
R² for halogen, cyano, nitro; each straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 6 carbon atoms; each straight-chain or branched haloalkyl, haloalkoxy or haloalkylthio each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms;
each straight-chain or branched alkoxycarbonyl or alkoximino alkyl each having 1 to 4 carbon atoms in the individual alkyl parts; Amino, aminocarbonyl; in each case straight-chain or branched alkyl amino, alkylaminocarbonyl, dialkylamino or dialkylaminocarbonyl each having 1 to 4 carbon atoms in the individual alkyl parts; each straight-chain or branched alkenyl, alkenyloxy or alkenylthio each having 2 to 4 carbon atoms; and optionally phenyl which is monosubstituted to trisubstituted, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and
R⁴ for halogen, cyano, nitro; straight-chain or branched alkyl having 2 to 6 carbon atoms; each straight-chain or branched alkoxy or alkylthio each having 1 to 6 carbon atoms; each straight-chain or branched haloalkyl; Haloalkoxy or haloalkylthio each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms;
each straight-chain or branched alkoxycarbonyl or alkoximino alkyl each having 1 to 4 carbon atoms in the individual alkyl parts; Amino, aminocarbonyl; in each case straight-chain or branched alkyl amino, alkylaminocarbonyl, dialkylamino or dialkylaminocarbonyl each having 1 to 4 carbon atoms in the individual alkyl parts; each straight-chain or branched alkenyl, alkenyloxy or alkenylthio each having 2 to 4 carbon atoms; and optionally phenyl which is monosubstituted to trisubstituted, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms;
or
R² for fluorine, bromine, iodine, cyano, nitro; straight-chain or branched alkyl having 2 to 6 carbon atoms; each straight-chain or branched alkoxy or alkylthio each having 1 to 6 carbon atoms; each straight-chain or branched haloalkyl; Haloalkoxy or haloalkylthio each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms;
each straight-chain or branched alkoxycarbonyl or alkoximino alkyl each having 1 to 4 carbon atoms in the individual alkyl parts; Amino, aminocarbonyl; in each case straight-chain or branched alkyl amino, alkylaminocarbonyl, dialkylamino or dialkylaminocarbonyl each having 1 to 4 carbon atoms in the individual alkyl parts; each straight-chain or branched alkenyl, alkenyloxy or alkenylthio each having 2 to 4 carbon atoms; and optionally phenyl which is monosubstituted to trisubstituted, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and
R⁴ represents methyl;
or
R² and R⁴ together represent straight-chain or branched alkylenedioxo or haloalkylenedioxo each having 1 to 4 carbon atoms and 1 to 8 identical or different halogen atoms.

in which
Ar² for the groups

stands,
wherein R¹, R², R³ and R⁴ are the same or different and are halogen, cyano, nitro; each straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 6 carbon atoms; each straight-chain or branched haloalkyl, haloalkoxy or haloalkylthio each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms;
each straight-chain or branched alkoxycarbonyl or alkoximino alkyl each having 1 to 4 carbon atoms in the individual alkyl parts; Amino, aminocarbonyl; in each case straight-chain or branched alkyl amino, alkylaminocarbonyl, dialkylamino or dialkylaminocarbonyl each having 1 to 4 carbon atoms in the individual alkyl parts; each straight-chain or branched alkenyl, alkenyloxy or alkenylthio each having 2 to 4 carbon atoms; and optionally phenyl which is monosubstituted to trisubstituted, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms;
or
each of R¹ and R² or R² and R⁴ or R³ and R⁴ together represent in each case straight-chain or branched alkylenedioxo or haloalkylenedioxo each having 1 to 4 carbon atoms and 1 to 8 identical or different halogen atoms.

The following groups of substances (a) to (g) of the formulas (Ia) to are particularly preferred (Ig):

in which
R1 is fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, n- or i-propyl; n-, i-, s- or t-butyl; n-, i-, s- or t-pentyl; Methoxy, ethoxy, n- or i-propoxy; n-, i-, s- or t-butoxy; Methylthio, ethylthio, n- or i-propylthio; n-, i-, s- or t-butylthio; Trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, difluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, methoximino ethyl, ethoximinomethyl, ethoximinoethyl;
Amino, aminocarbonyl, methylamino, ethylamino, n- or i-propyl amino, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propyl aminocarbonyl, dimethylamino, ethylmethylamino, methyl-n-propylamino, methyl-i-propylamino, diethylamino, dimethylaminocarbonocarbonyl, ethylmethylamin , Methyl-n-propylaminocarbonyl, methyl-i-propylaminocarbonyl, diethylaminocarbonyl, propenyl, butenyl, isobutyl, propenyloxy, butenyloxy, isobutenyloxy, propenylthio, butenylthio, isobutenylthio;
or phenyl which is optionally mono- to trisubstituted, identically or differently, by fluorine, chlorine, bromine, methyl and / or ethyl.

in which
R² is fluorine, iodine, cyano, nitro, ethyl, n- or i-propyl; n-, i-, s- or t-butyl; n-, i-, s- or t-pentyl; Methoxy, ethoxy, n- or i-propoxy; n-, i-, s- or t-butoxy; Methylthio, ethylthio, n- or i-propylthio; n-, i-, s- or t-butylthio; Difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, difluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, methoximinoethyl, ethoximinomethyl, ethoximino ethyl;
Amino, aminocarbonyl, methylamino, ethylamino, n- or i-propyl amino, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propyl aminocarbonyl, dimethylamino, ethylmethylamino, methyl-n-propylamino, methyl-i-propylamino, diethylamino, dimethylaminocarbonocarbonyl, ethylmethylamin , Methyl-n-propylaminocarbonyl, methyl-i-propylaminocarbonyl, diethylaminocarbonyl, propenyl, butenyl, isobutyl, propenyloxy, butenyloxy, isobutenyloxy, propenylthio, butenylthio, isobutenylthio;
or phenyl which is optionally mono- to trisubstituted, identically or differently, by fluorine, chlorine, bromine, methyl and / or ethyl.

in which
R⁴ for fluorine, bromine, iodine, cyano, nitro, n-, i-, s- or t-butyl; n-, i-, s- or t-pentyl; Ethoxy, n- or i-propoxy; n-, i-, s- or t-butoxy; Methylthio, ethylthio, n- or i-propylthio; n-, i-, s- or t-butylthio; Difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, difluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, methoximino ethyl, ethoximinomethyl, ethoximinoethyl;
Amino, aminocarbonyl, methylamino, ethylamino, n- or i-propyl amino, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propyl aminocarbonyl, dimethylamino, ethylmethylamino, methyl-n-propylamino, methyl-i-propylamino, diethylamino, dimethylaminocarbonocarbonyl, ethylmethylamin , Methyl-n-propylaminocarbonyl, methyl-i-propylaminocarbonyl, diethylaminocarbonyl, propenyl, butenyl, isobutyl, propenyloxy, butenyloxy, isobutenyloxy, propenylthio, butenylthio, isobutenylthio;
or phenyl which is optionally mono- to trisubstituted, identically or differently, by fluorine, chlorine, bromine, methyl and / or ethyl.

in which
Ar¹ for the groupings

stands,
wherein R¹, R², R³ and R⁴ are the same or different and are fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, n- or i-propyl; n-, i-, s- or t-butyl; n-, i-, s- or t-pentyl; Methoxy, ethoxy, n- or i-propoxy; n-, i-, s- or t-butoxy; Methylthio, ethylthio, n- or i-propylthio; n-, i-, s- or t-butylthio; Trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, difluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, methoximinoethyl, ethoximino methyl, ethoximinoethyl;
Amino, aminocarbonyl, methylamino, ethylamino, n- or i-propyl amino, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propyl aminocarbonyl, dimethylamino, ethylmethylamino, methyl-n-propylamino, methyl-i-propylamino, diethylamino, dimethylaminocarbonocarbonyl, ethylmethylamin , Methyl-n-propylaminocarbonyl, methyl-i-propylaminocarbonyl, diethylaminocarbonyl, propenyl, butenyl, isobutyl, propenyloxy, butenyloxy, isobutenyloxy, propenylthio, butenylthio, isobutenylthio;
or optionally phenyl which is mono- to trisubstituted, identically or differently, by fluorine, chlorine, bromine, methyl and / or ethyl;
or R¹ and R² together represent methylenedioxo, ethylenedioxo, difluoromethylenedioxo or tetrafluoroethylene dioxo.

in which
R² for fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, n- or i-propyl; n-, i-, s- or t-butyl; n-, i-, s- or t-pentyl; Methoxy, ethoxy, n- or i-propoxy; n-, i-, s- or t-butoxy; Methylthio, ethylthio, n- or i-propylthio; n-, i-, s- or t-butylthio; Trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, difluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, methoximino ethyl, ethoximinomethyl, ethoximinoethyl;
Amino, aminocarbonyl, methylamino, ethylamino, n- or i-propyl amino, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propyl aminocarbonyl, dimethylamino, ethylmethylamino, methyl-n-propylamino, methyl-i-propylamino, diethylamino, dimethylaminocarbonocarbonyl, ethylmethylamin , Methyl-n-propylaminocarbonyl, methyl-i-propylaminocarbonyl, diethylaminocarbonyl, propenyl, butenyl, isobutyl, propenyloxy, butenyloxy, isobutenyloxy, propenylthio, butenylthio, isobutenylthio;
or optionally mono- to trisubstituted, identically or differently, by fluorine, chlorine, bromine, methyl and / or ethyl substituted phenyl and
R³ for fluorine, bromine, iodine, cyano, nitro, methyl, ethyl, n- or i-propyl; n-, i-, s- or t-butyl; n-, i-, s- or t-pentyl; Methoxy, ethoxy, n- or i-propoxy; n-, i-, s- or t-butoxy; Methylthio, ethylthio, n- or i-propylthio; n-, i-, s- or t-butylthio; Trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, difluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, methoximino ethyl, ethoximinomethyl, ethoximinoethyl;
Amino, aminocarbonyl, methylamino, ethylamino, n- or i-propyl amino, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propyl aminocarbonyl, dimethylamino, ethylmethylamino, methyl-n-propylamino, methyl-i-propylamino, diethylamino, dimethylaminocarbonocarbonyl, ethylmethylamin , Methyl-n-propylaminocarbonyl, methyl-i-propylaminocarbonyl, diethylaminocarbonyl, propenyl, butenyl, isobutyl, propenyloxy, butenyloxy, isobutenyloxy, propenylthio, butenylthio, isobutenylthio;
or phenyl which is optionally mono- to trisubstituted, identically or differently, by fluorine, chlorine, bromine, methyl and / or ethyl.

in which
R² for fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, n- or i-propyl; n-, i-, s- or t-butyl; n-, i-, s- or t-pentyl; Methoxy, ethoxy, n- or i-propoxy; n-, i-, s- or t-butoxy; Methylthio, ethylthio, n- or i-propylthio; n-, i-, s- or t-butylthio; Trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, difluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, methoximino ethyl, ethoximinomethyl, ethoximinoethyl;
Amino, aminocarbonyl, methylamino, ethylamino, n- or i-propyl amino, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propyl aminocarbonyl, dimethylamino, ethylmethylamino, methyl-n-propylamino, methyl-i-propylamino, diethylamino, dimethylaminocarbonocarbonyl, ethylmethylamin , Methyl-n-propylaminocarbonyl, methyl-i-propylaminocarbonyl, diethylaminocarbonyl, propenyl, butenyl, isobutyl, propenyloxy, butenyloxy, isobutenyloxy, propenylthio, butenylthio, isobutenylthio;
or optionally mono- to trisubstituted, identically or differently, by fluorine, chlorine, bromine, methyl and / or ethyl substituted phenyl and
R⁴ for fluorine, chlorine, bromine, iodine, cyano, nitro, ethyl, n- or i-propyl; n-, i-, s- or t-butyl; n-, i-, s- or t-pentyl; Methoxy, ethoxy, n- or i-propoxy; n-, i-, s- or t-butoxy; Methylthio, ethylthio, n- or i-propylthio; n-, i-, s- or t-butylthio; Trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, difluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, methoximino ethyl, ethoximinomethyl, ethoximinoethyl;
Amino, aminocarbonyl, methylamino, ethylamino, n- or i-propyl amino, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propyl aminocarbonyl, dimethylamino, ethylmethylamino, methyl-n-propylamino, methyl-i-propylamino, diethylamino, dimethylaminocarbonocarbonyl, ethylmethylamin , Methyl-n-propylaminocarbonyl, methyl-i-propylaminocarbonyl, diethylaminocarbonyl, propenyl, butenyl, isobutyl, propenyloxy, butenyloxy, isobutenyloxy, propenylthio, butenylthio, isobutenylthio;
or optionally phenyl which is mono- to trisubstituted, identically or differently, by fluorine, chlorine, bromine, methyl and / or ethyl,
or
R² is fluorine, bromine, iodine, cyano, nitro, ethyl, n- or i-propyl; n-, i-, s- or t-butyl; n-, i-, s- or t-pentyl; Methoxy, ethoxy, n- or i-propoxy; n-, i-, s- or t-butoxy; Methylthio, ethylthio, n- or i-propylthio; n-, i-, s- or t-butylthio; Trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, difluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, methoximinoethyl, ethoximino methyl, ethoximinoethyl;
Amino, aminocarbonyl, methylamino, ethylamino, n- or i-propyl amino, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propyl aminocarbonyl, dimethylamino, ethylmethylamino, methyl-n-propylamino, methyl-i-propylamino, diethylamino, dimethylaminocarbonocarbonyl, ethylmethylamin , Methyl-n-propylaminocarbonyl, methyl-i-propylaminocarbonyl, diethylaminocarbonyl, propenyl, butenyl, isobutyl, propenyloxy, butenyloxy, isobutenyloxy, propenylthio, butenylthio, isobutenylthio;
or optionally mono- to trisubstituted, identically or differently, by fluorine, chlorine, bromine, methyl and / or ethyl substituted phenyl and
R⁴ represents methyl;
or
R² and R⁴ together represent methylenedioxo, ethylenedioxo, difluoromethylenedioxo or tetrafluoroethylene dioxo.

in which
Ar² for the groups

stands,
wherein R¹, R², R³ and R⁴ are the same or different and are fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, n- or i-propyl; n-, i-, s- or t-butyl; n-, i-, s- or t-pentyl; Methoxy, ethoxy, n- or i-propoxy; n-, i-, s- or t-butoxy; Methylthio, ethylthio, n- or i-propylthio; n-, i-, s- or t-butylthio; Trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, difluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, methoximinoethyl, ethoximino methyl, ethoximinoethyl;
Amino, aminocarbonyl, methylamino, ethylamino, n- or i-propyl amino, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propyl aminocarbonyl, dimethylamino, ethylmethylamino, methyl-n-propylamino, methyl-i-propylamino, diethylamino, dimethylaminocarbonocarbonyl, ethylmethylamin , Methyl-n-propylaminocarbonyl, methyl-i-propylaminocarbonyl, diethylaminocarbonyl, propenyl, butenyl, isobutyl, propenyloxy, butenyloxy, isobutenyloxy, propenylthio, butenylthio, isobutenylthio;
or optionally phenyl which is mono- to trisubstituted, identically or differently, by fluorine, chlorine, bromine, methyl and / or ethyl;
or
each R¹ and R² or R² and R⁴ or R³ and R⁴ together drove methylenedioxo, ethylenedioxo, difluoromethylenedioxo or tetrafluoroethylenedioxo.

The following groups of substances (a) to (g) of the formulas are very particularly preferred (Ia) to (Ig):

in which
R1 is fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, n- or i-propyl; n-, i-, s- or t-butyl; n-, i-, s- or t-pentyl; Methoxy, ethoxy, n- or i-propoxy; n-, i-, s- or t-butoxy; Methylthio, ethylthio, n- or i-propylthio; n-, i-, s- or t-butylthio; Trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, difluoromethylthio, methoxycarbonyl, ethoxycarbonyl;
Methylamino, ethylamino, methylaminocarbonyl, ethylaminocarbonyl, dimethylamino, ethylmethylamino, diethylamino, dimethylamino carbonyl, ethylmethylaminocarbonyl, diethylaminocarbonyl, propenyloxy, butenyloxy, isobutenyloxy, propenylthio, butenylthio or isobutenylthio.

in which
R² is fluorine, iodine, cyano, nitro, ethyl, n- or i-propyl; n-, i-, s- or t-butyl; n-, i-, s- or t-pentyl; Methoxy, ethoxy, n- or i-propoxy; n-, i-, s- or t-butoxy; Methylthio, ethylthio, n- or i-propylthio; n-, i-, s- or t-butylthio; Difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, difluoromethylthio, methoxycarbonyl, ethoxycarbonyl;
Methylamino, ethylamino, methylaminocarbonyl, ethylaminocarbonyl, dimethylamino, ethylmethylamino, diethylamino, dimethylamino carbonyl, ethylmethylaminocarbonyl, diethylaminocarbonyl, propenyloxy, butenyloxy, isobutenyloxy, propenylthio, butenylthio or isobutenylthio.

in which
R⁴ for fluorine, bromine, iodine, cyano, nitro, n-, i-, s- or t-butyl; n-, i-, s- or t-pentyl; Ethoxy, n- or i-propoxy; n-, i-, s- or t-butoxy; Methylthio, ethylthio, n- or i-propylthio; n-, i-, s- or t-butylthio; Difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, difluoromethylthio, methoxycarbonyl, ethoxycarbonyl;
Methylamino, ethylamino, methylaminocarbonyl, ethylaminocarbonyl, dimethylamino, ethylmethylamino, diethylamino, dimethylamino carbonyl, ethylmethylaminocarbonyl, diethylaminocarbonyl, propenyloxy, butenyloxy, isobutenyloxy, propenylthio, butenylthio or isobutenylthio.

in which
Ar¹ for the groupings

stands,
wherein R¹, R², R³ and R⁴ are the same or different and are fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, n- or i-propyl; n-, i-, s- or t-butyl; n-, i-, s- or t-pentyl; Methoxy, ethoxy, n- or i-propoxy; n-, i-, s- or t-butoxy; Methylthio, ethylthio, n- or i-propylthio; n-, i-, s- or t-butylthio; Trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, difluoromethylthio, methoxycarbonyl, ethoxycarbonyl;
Methylamino, ethylamino, methylaminocarbonyl, ethylaminocarbonyl, dimethylamino, ethylmethylamino, diethylamino, dimethylamino carbonyl, ethylmethylaminocarbonyl, diethylaminocarbonyl, propenyloxy, butenyloxy, isobutenyloxy, propenylthio, butenylthio or isobutenylthio;
or R¹ and R² together represent methylenedioxo, ethylenedioxo, difluoromethylenedioxo or tetrafluoroethylene dioxo.

in which
R² for fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, n- or i-propyl; n-, i-, s- or t-butyl; n-, i-, s- or t-pentyl; Methoxy, ethoxy, n- or i-propoxy; n-, i-, s- or t-butoxy; Methylthio, ethylthio, n- or i-propylthio; n-, i-, s- or t-butylthio; Trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, difluoromethylthio, methoxycarbonyl, ethoxycarbonyl;
Methylamino, ethylamino, methylaminocarbonyl, ethylaminocarbonyl, dimethylamino, ethylmethylamino, diethylamino, dimethylamino carbonyl, ethylmethylaminocarbonyl, diethylaminocarbonyl, propenyloxy, butenyloxy, isobutenyloxy, propenylthio, butenylthio or isobutenylthio
R³ for fluorine, bromine, iodine, cyano, nitro, methyl, ethyl, n- or i-propyl; n-, i-, s- or t-butyl; n-, i-, s- or t-pentyl; Methoxy, ethoxy, n- or i-propoxy; n-, i-, s- or t-butoxy; Methylthio, ethylthio, n- or i-propylthio; n-, i-, s- or t-butylthio; Trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, difluoromethylthio, methoxycarbonyl, ethoxycarbonyl;
Methylamino, ethylamino, methylaminocarbonyl, ethylaminocarbonyl, dimethylamino, ethylmethylamino, diethylamino, dimethylamino carbonyl, ethylmethylaminocarbonyl, diethylaminocarbonyl, propenyloxy, butenyloxy, isobutenyloxy, propenylthio, butenylthio or isobutenylthio.

in which
R² for fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, n- or i-propyl; n-, i-, s- or t-butyl; n-, i-, s- or t-pentyl; Methoxy, ethoxy, n- or i-propoxy; n-, i-, s- or t-butoxy; Methylthio, ethylthio, n- or i-propylthio; n-, i-, s- or t-butylthio; Trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, difluoromethylthio, methoxycarbonyl, ethoxycarbonyl;
Methylamino, ethylamino, methylaminocarbonyl, ethylaminocarbonyl, dimethylamino, ethylmethylamino, diethylamino, dimethylamino carbonyl, ethylmethylaminocarbonyl, diethylaminocarbonyl, propenyloxy, butenyloxy, isobutenyloxy, propenylthio, butenylthio or isobutenylthio
R⁴ for fluorine, chlorine, bromine, iodine, cyano, nitro, ethyl, n- or i-propyl; n-, i-, s- or t-butyl; n-, i-, s- or t-pentyl; Methoxy, ethoxy, n- or i-propoxy; n-, i-, s- or t-butoxy; Methylthio, ethylthio, n- or i-propylthio; n-, i-, s- or t-butylthio; Trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, difluoromethylthio, methoxycarbonyl, ethoxycarbonyl;
Methylamino, ethylamino, methylaminocarbonyl, ethylaminocarbonyl, dimethylamino, ethylmethylamino, diethylamino, dimethylamino carbonyl, ethylmethylaminocarbonyl, diethylaminocarbonyl, propenyloxy, butenyloxy, isobutenyloxy, propenylthio, butenylthio or isobutenylthio;
or optionally phenyl which is mono- to trisubstituted, identically or differently, by fluorine, chlorine, bromine, methyl and / or ethyl;
or
R² is fluorine, bromine, iodine, cyano, nitro, ethyl, n- or i-propyl; n-, i-, s- or t-butyl; n-, i-, s- or t-pentyl; Methoxy, ethoxy, n- or i-propoxy; n-, i-, s- or t-butoxy; Methylthio, ethylthio, n- or i-propylthio; n-, i-, s- or t-butylthio; Trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, difluoromethylthio, methoxycarbonyl, ethoxycarbonyl;
Methylamino, ethylamino, methylaminocarbonyl, ethylaminocarbonyl, dimethylamino, ethylmethylamino, diethylamino, dimethylamino carbonyl, ethylmethylaminocarbonyl, diethylaminocarbonyl, propenyloxy, butenyloxy, isobutenyloxy, propenylthio, butenylthio or isobutenylthio
R⁴ represents methyl;
or
R² and R⁴ together represent methylenedioxo, ethylenedioxo, difluoromethylenedioxo or tetrafluoroethylene dioxo.

in which
Ar² for the groups

stands,
wherein R¹, R², R³ and R⁴ are the same or different and are fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, n- or i-propyl; n-, i-, s- or t-butyl; n-, i-, s- or t-pentyl; Methoxy, ethoxy, n- or i-propoxy; n-, i-, s- or t-butoxy; Methylthio, ethylthio, n- or i-propylthio; n-, i-, s- or t-butylthio; Trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, difluoromethylthio, methoxycarbonyl, ethoxycarbonyl;
Methylamino, ethylamino, methylaminocarbonyl, ethylaminocarbonyl, dimethylamino, ethylmethylamino, diethylamino, dimethylamino carbonyl, ethylmethylaminocarbonyl, diethylaminocarbonyl, propenyloxy, butenyloxy, isobutenyloxy, propenylthio, butenylthio or isobutenylthio;
or
R¹ and R² or R² and R⁴ or R³ and R⁴ together represent methylenedioxo, ethylenedioxo, difluoromethylenedioxo or tetrafluoroethylenedioxo.

For example, 2-hydroxy-4-trifluoromethylbenzoic acid and 3-chloro-4-fluoroaniline are used as starting materials, the course of the reaction of represent the inventive method by the following formula:

The material required to carry out the process according to the invention as a starting material 2-Hydroxy-4-trifluoromethylbenzoic acid or its esters are represented by the formula (II) generally defined. In this formula, R is preferably hydrogen or straight-chain or branched alkyl having 1 to 4 carbon atoms. The 2-hydroxy 4-trifluoromethylbenzoic acid or its esters are known (see, for example, WO-A 92/17066).

Which also to carry out the method according to the invention as Anilines required as starting materials are generally defined by the formula (in). In Ar has preferably or particularly preferably those of this formula Meanings already related to the description of the Compounds of formula (I) as preferred or particularly preferred for this Substituents were specified. The anilines of formula (III) are general known compounds of organic chemistry.

The inventive method is in the presence of a suitable Condensing agent carried out. As such, everyone usually comes for Condensation agents that can be used in such amidation reactions. Example acid halide formers such as phosphorus tribromide, phosphorus trichloride, Phosphorus pentachloride, phosphorus oxychloride or thionyl chloride; Anhydride formers such as Ethyl chloroformate or methanesulfonyl chloride; Carbodiimides such as N, N'-dicyclohexylcarbodiimide (DCC) or other conventional condensing agents, such as N, N'-carbonyldiimidazole, 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ) or Triphenylphosphine / carbon tetrachloride.  

As a diluent for carrying out the method according to the invention inert organic solvents are suitable. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated carbons Hydrogen, such as gasoline, benzene, toluene, xylene, chlorobenzene, Dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, Carbon tetrachloride; Ethers, such as diethyl ether, diisopropyl ether, dioxane, Tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones, such as acetone, Butanone or methyl isobutyl ketone; Nitriles, such as acetonitrile, propionitrile or Benzonitrile; Amides, such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; or sulfoxides such as dimethyl sulfoxide.

The process according to the invention is optionally carried out in the presence of a suitable Reaction auxiliary carried out. All the usual inorganic ones come as such or organic bases in question. These include, for example, alkaline earth or Alkali metal hydroxides such as sodium hydroxide, calcium hydroxide, potassium hydroxide or also ammonium hydroxide, alkali metal carbonates, such as sodium carbonate, Potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate or Ammonium carbonate, alkali or alkaline earth metal acetates, such as sodium acetate, potassium acetate, calcium acetate or ammonium acetate, and tertiary amines, such as Trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, pyridine, N-methylpiperidine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), Diazabicyclonones (DBN) or Diazabicycloundecen (DBU).

The reaction temperatures can be carried out when carrying out the process according to the invention Process can be varied over a wide range. Generally you work at temperatures between -60 ° C and 220 ° C, preferably at temperatures between 20 ° C and 180 ° C.

To carry out the process according to the invention, 2-hydroxy-4-trifluoromethylbenzoic acid is used per mole or their esters of the formula (II) in generally 1.0 to 2.0 mol, preferably 1.0 to 1.3 mol, of aniline of the formula (III), 0.3 to 5.0 moles, preferably 0.5 to 2.0 moles of condensing agent and optionally 0 to 5.0 mol, preferably 0 to 2.5 mol, of reaction auxiliaries  base used. Carrying out the reaction, working up and isolating the Reaction products are carried out according to known methods.

The active compounds of the formula (I) according to the invention have a strong activity against Pests on and can help fight unwanted pests can be used practically. The active ingredients are for use as fungicides in the Suitable for crop protection and material protection. In addition, the Active substances according to the invention for controlling animal pests.

Fungicides are used in crop protection to combat Plasmodiophoromycetes Oomycetes Chytridiomycetes Zygomycetes, Ascomycetes Basidiomycetes and Deuteromycetes.

Some pathogens of fungal diseases that fall under the generic names listed above may be mentioned as examples, but not by way of limitation:
Pythium species, such as, for example, Pythium ultimum;
Phytophthora species, such as, for example, Pseudoperonospora humuli or Pseudopero nospora cubensis;
Plasmopara species, such as, for example, Plasmopara viticola;
Peronospora species, such as, for example, Peronospora pisi or P. brassicae;
Erysiphe species, such as, for example, Erysiphe graminis;
Sphaerotheca species, such as, for example, Sphaerotheca fuliginea;
Podosphaera species, such as, for example, Podosphaera leucotricha;
Venturia species, such as, for example, Venturia inaequalis;
Pyrenophora species, such as, for example, Pyrenophora teres or P. graminea (conidia form: Drechslera, Syn: Helminthosporium);
Cochliobolus species, such as, for example, Cochliobolus sativus (conidial form: Drechlera, Syn: Helminthosporium);
Uromyces species, such as, for example, Uromyces appendiculatus;
Puccinia species, such as, for example, Puccinia recondita;
Tilletia species, such as, for example, Tilletia caries;
Ustilago species, such as, for example, Ustilago nuda or Ustilago avenae;
Pellucularia species, such as, for example, Pellicularia sasakii;
Pyricularia species, such as, for example, Pyricularia oryzae;
Fusarium species, such as, for example, Fusarium culmorum;
Botrytis species, such as, for example, Botrytis cinerea;
Septoria species, such as, for example, Septoria nodorum;
Leptosphaeria species, such as, for example, Leptosphaeria nodorum;
Cercospora species, such as, for example, Cercospora canescens;
Alternaria species, such as, for example, Alternaria brassicae;
Pseudocercosporella species, such as, for example, Pseudocercosporella herpotrichoides.

The good plant tolerance of the active ingredients in the fight against Concentrations necessary for plant diseases allow treatment of above-ground parts of plants, planting and seeds, and the soil.

The active compounds according to the invention can be used with particularly good success Combating diseases in fruit and vegetable growing, such as against the pathogen of tomato brown rot (Phytophthora infestans) or against the pathogen of downy mildew on vines (Plasmopara viticola) or to control Cereal diseases, such as, for example, against the pathogen causing the brown fur of the Wheat (Septoria nodorum) or against the causative agent of brown spot disease Barley or wheat (Cochliobolus sativus) or against the pathogen of the Net spot disease of barley (Pyrenophora teres) or to combat rice diseases, such as against the rice stain pathogen (Pyricularia oryzae) or against the causative agent of rice stalk disease (Pellicularia sasakii) can be used.

In addition, the active compounds according to the invention have a good in vitro effect.

In addition, the active compounds according to the invention are suitable for combating animal pests, preferably arthropods and nematodes, in particular Insects and arachnids, which are used in agriculture, in forests, in stock and Material protection and in the hygiene sector. You are against normal sensitive and resistant species as well as against all or individual stages of development effective. The pests mentioned above include:  

From the order of the Isopoda z. B. Oniscus asellus, Armadillidium vulgare, Porcellio scaber.

From the order of the Diplopoda z. B. Blaniulus guttulatus.

From the order of the Chilopoda z. B. Geophilus carpophagus, Scutigera spec.

From the order of the Symphyla z. B. Scutigerella immaculata.

From the order of the Thysanura z. B. Lepisma saccharina.

From the order of the Collembola z. B. Onychiums armatus.

From the order of Orthoptera z. B. Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis, Schistocerca gregaria.

From the order of the Dermaptera z. B. Auricular Forficula.

From the order of the Isoptera z. B. Reticulitermes spp.

From the order of the Anoplura z. B. Phylloxera vastatrix, Pemphigus spp., Pediculus humanus corporis, Haematopinus spp., Linognathus spp.

From the order of the Mallophaga z. B. Trichodectes spp., Damalinea spp.

From the order of the Thysanoptera z. B. Hercinothrips femoralis, Thrips tabaci.

From the order of Heteroptera z. B. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.

From the order of Homoptera z. B. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Doralis pomi, Eriosoma lanigemm, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. Psylla spp.

From the order of the Lepidoptera z. B. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp. Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Spodoptera exigua, Mamestra brassicae, Panolis flammea, Prodenia litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella,  Tineola bisselliella, Tinea pellionella, Hofmannophila pseudospretella, Cacoecia po dana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana.

From the order of the Coleoptera z. B. Anobium punctatum, Rhizopertha dominica, Acanthoscelides obtectus, Bruchidius obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica.

From the order of the Hymenoptera z. B. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.

From the order of the Diptera z. B. Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Famia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa.

From the order of the Siphonaptera z. B. Xenopsylla cheopis, Ceratophyllus spp.

From the order of the Arachnida z. B. Scorpio maurus, Latrodectus mactans.

From the order of Acarina z. B. Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp.

Plant parasitic nematodes include Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp.  

The active compounds of the formula (I) according to the invention are also notable for excellent acaricidal activity, such as B. against the common spider mite (Tetranychus urticae); as well as excellent insecticides or leaf insecticides Effect, such as B. against the larvae of the cockroach (Plutella xylostella) or against the caterpillars of the cockroach (Plutella maculipennis) or the horseradish leaf beetle Larvae (Phaedon cochleariae) from.

The active compounds according to the invention can also protect techni materials against infestation and destruction by unwanted microorganisms be used.

In the present context, technical materials include non-living ones Understand materials that have been prepared for use in engineering are. For example, technical materials can be created by the invention Active substances are to be protected against microbial change or destruction, Adhesives, glues, paper and cardboard, textiles, leather, wood, paints and Plastic items, coolants and other materials can be made by micro organisms can be attacked or decomposed. As part of the to be protected Materials are also parts of production plants, such as cooling water Circuits, called who impaired by the multiplication of microorganisms that can. Within the scope of the present invention as technical materials preferably adhesives, glues, papers and cartons, leather, wood, paints, Called cooling lubricants and heat transfer fluids, especially before moves wood.

The substances according to the invention are preferably suitable for protecting paints against infestation and destruction by microorganisms.

As microorganisms that break down or change the technical Ma materials can be, for example, bacteria, fungi, yeasts, algae and Called slime organisms. The active compounds according to the invention preferably act against fungi, in particular mold, wood-discoloring and wood-destroying fungi (Basidiomycetes) and against mucous organisms and algae.

For example, microorganisms of the following genera may be mentioned:
Alternaria, such as Alternaria tenuis,
Aspergillus, such as Aspergillus niger;
Chaetomium, such as Chaetominum globosum;
Coniophora, such as Coniophora puteana;
Lentinus such as Lentinus tigrinus;
Penicillium such as Penicillium glaucum;
Polyporus, such as Polyporus versicolor;
Aureobasidium such as aureobasidium pullulans;
Sclerophoma, such as Sclerophoma pityophila;
Trichoderma, such as Trichoderma viride;
Escherichia, such as Escherichia coli;
Pseudomonas, such as Pseudomonas aeruginosa;
Staphylococcus, such as Staphylococcus aureus.

Depending on the area of application, the active ingredients can depend on their because of physical and / or chemical properties in common formulations such as solutions, emulsions, suspensions, powders, Foams, pastes, granules, aerosols, very fine encapsulations in polymeric substances and in coating compositions for seeds, as well as ULV cold and warm mist formulations.

These formulations are prepared in a known manner, e.g. B. by mixing of active ingredients with extenders, i.e. liquid solvents, under pressure standing liquefied gases and / or solid carriers, optionally under Use of surface-active agents, i.e. emulsifiers and / or Dispersing agents and / or foaming agents. In case of using Water as an extender can e.g. B. also organic solvents, such as Alcohols can be used as auxiliary solvents. As a liquid solvent essentially come into question: aromatics, such as xylene, toluene, alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as Chlorobenzenes, chlorethylenes, such as 1,2-dichloroethane or methylene chloride, aliphatic Hydrocarbons such as cyclohexane or paraffins, e.g. B. gasoline or others Petroleum fractions, alcohols, such as ethanol, isopropanol, butanol, benzyl alcohol or Glycol and their ethers and esters, ketones, such as acetone, methyl ethyl ketone, Methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethyl  formamide or dimethyl sulfoxide, as well as water; with liquefied gaseous Extenders or carriers are liquids that are nor painter temperature and under normal pressure are gaseous, z. B. aerosol propellants, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide; as solid carriers come into question: B. natural stone powder, such as kaolins, Clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as finely divided silica, aluminum oxide and Silicates; as solid carriers for granules come into question: z. B. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite as well synthetic granules from inorganic and organic flours as well as granules made of organic material such as sawdust, coconut shells, corn cobs and Tobacco stem; as emulsifying and / or foam-generating agents come into question: z. B. non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, Polyoxyethylene fatty alcohol ether, e.g. B. alkylaryl polyglycol ethers, alkyl sulfonates, Alkyl sulfates, aryl sulfonates and protein hydrolyzates; come as a dispersant in question: e.g. B. Ligninsulfitablaugen and methyl cellulose.

Adhesives such as carboxymethyl cellulose, natural, can be used in the formulations and synthetic, powdery, granular or latex-shaped polymers are used, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospho lipids such as cephalins and lecithins and synthetic phospholipids. Other additives can be mineral and vegetable oils.

Dyes such as inorganic pigments, e.g. B. iron oxide, titanium oxide, ferro cyan and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, Molybdenum and zinc can be used.

In crop protection, the formulations generally contain between 0.1 and 95 Weight percent active ingredient, preferably between 0.5 and 90%.

The active compounds according to the invention can be used as such when used as fungicides or in their formulations also in a mixture with known fungicides, bactericides, Acaricides, nematicides or insecticides can be used, e.g. B. that  To broaden the spectrum of activity or to prevent the development of resistance. In many In this case, synergistic effects are obtained, i. H. the effectiveness of the mixture is greater than the effectiveness of the individual components.

Particularly cheap mixing partners are e.g. B. the following connections:

Fungicides

2-aminobutane; 2-anilino-4-methyl-6-cyclopropyl-pyrimidine; 2 ′, 6′-dibromo-2-methyl-4′-trifluoromethoxy-4′-trifluoromethyl-1,3-thiazole-5-carboxanilide; 2,6-dichloro-N- (4-trifluoromethylbenzyl) benzamide; (E) -2-methoxyimino-N-methyl-2- (2-phenoxyphenyl) acetamide; 8-hydroxyquinoline sulfate; Methyl- (E) -2- {2- [6- (2-cyanophenoxy) pyrimidin-4-yloxy] phenyl} -3-methoxyacrylate; Methyl (E) methoximlno [alpha- (o-tolyloxy) -o-tolyl] acetate; 2-phenylphenol (OPP), aldimorph, ampropylfos, anilazine, azaconazole,
Benalaxyl, Benodanil, Benomyl, Binapacryl, Biphenyl, Bitertanol, Blasticidin-S, Bromuconazole, Bupirimate, Buthiobate,
Calcium polysulfide, captafol, captan, carbendazim, carboxin, quinomethionate (quinomethionate), chloroneb, chloropicrin, chlorothalonil, chlozolinate, cufraneb, cymoxanil, cyproconazole, cyprofuram,
Dichlorophene, diclobutrazole, diclofluanid, diclomezin, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole, dinocap, diphenylamine, dipyrithione, ditalimfos, dithianon, dodine, drazoxolone,
Edifenphos, epoxyconazole, ethirimol, etridiazole,
Fenarimol, Fenbuconazole, Fenfuram, Fenitropan, Fenpiclonil, Fenpropidin, Fenpropimorph, Fentinacetat, Fentinhydroxyd, Ferbam, Ferimzone, Fluazinam, Fludioxonil, Fluoromide, Fluquinconazole, Flusilazole, Flusulfamide, Flutolanyl, Fuberilafil, Fuberri Furmecyclox, guazatine,
Hexachlorobenzene, hexaconazole, hymexazole,
Imazalil, Imibenconazol, Iminoctadin, Iprobefos (IBP), Iprodion, Isoprothiolan, Kasugamycin, copper preparations, such as: copper hydroxide, copper phthalate, copper oxychloride, copper sulfate, copper oxide, oxine-copper and Bordeaux mixture, Mancopper, Mancozeb, Maneb, Mepan , Metalaxyl, metconazole, methasulfocarb, methfuroxam, metiram, metsulfovax, myciobutanil,
Nickel dimethyidithiocarbamate, Nitrothal isopropyl, Nuarimol,
Ofurace, Oxadixyi, Oxamocarb, Oxycarboxin,
Pefurazoat, Penconazoi, Pencycuron, Phosdiphen, Pimaricin, Piperalin, Polyoxin, Probenazol, Prochloraz, Procymidon, Propamocarb, Propiconazoie, Propineb, Pyrazophos, Pyrifenox, Pyrimethanil, Pyroquilon,
Quintozen (PCNB),
Sulfur and sulfur preparations,
Tebuconazole, tecloftalam, tecnazene, tetraconazole, thiabendazole, Thicyofen, thiophanate-methyl, thiram, Tolclophos-methyl, tolylfluanid, triadimefon, triadimenol, triazoxide, Trichlamid, tricyclazole, tridemorph, triflumizole, triforine, triticonazole,
Validamycin A, vinclozolin,
Zineb, ziram

Bactericides

Bronopol, dichlorophene, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, Octhilinone, furan carboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, Copper sulfate and other copper preparations.

Insecticides / acaricides / nematicides

Abamectin, Abamectin, AC 303 630, Acephat, Acrinathrin, Alanycarb, Aldicarb, Alpha methrin, Amitraz, Avermectin, AZ 60541, Azadirachtin, Azinphos A, Azinphos M, Azocyciotin,
Bacillus thuringiensis, Bendiocarb, Benfuracarb, Bensultap, Betacyluthrin, Bifenthrin, BPMC, Brofenprox, Bromophos A, Bufencarb, Buprofezin, Butocarboxin, Butylpyridaben,
Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, CGA 157 419, CGA 184699, Chloethocarb, Chlorethoxyfos, Chlorfenvinphos, Chlorfluazuron, Chlormephos, Chlorpyrifos, Chlorpyrifos M, Cis-Resmethrin, Clocythrinhrhrhrinhrhrinhrinhrinhrinhrinhrinhrinhrinhrinhrinhrinhrinhrinhrinhrinhrinhrinhrinhrinhrinhrofhrinhrinhrinhrinhrinhrinhrinhrinhrinhrinhrinhrofhrinhrinhrinhrinhrinhrinhrinhrinhrinhrofhrinhrinhrinhrhrinhrhrinhrhrinhrhrinhrinhrofhrinophhrinhrinhrinhrinhrinhrinhrinhrinhrinhrhrinhrhrinhrinhrhrinhrhrinhrhrinhrhrinhrofhrine Cyhexatin, Cypermethrin, Cyromazin, Deltamethrin, Demeton M, Demeton S, Demeton-S-methyl, Diafenthiuron, Diazinon, Dichlofenthion, Dichlorvos, Dicliphos, Dicrotophos, Diethion, Diflubenzuron, Dimethoat, Dimathionionphosphinulioxin
Edifenphos, Emamectin, Esfenvalerat, Ethiofencarb, Ethion, Ethofenprox, Ethoprophos, Etrimphos,
Fenamiphos, Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipronil, Fluazinam, Flucycloxuron, Flucythrinat, Flufenoxuron, Flufenothxinfox, Fufionophon, Fufionophon, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufon
HCH, heptenophos, hexaflumuron, hexythiazox,
Imidacloprid, Iprobefos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Ivemectin, Lamda-cyhalothrin, Lufenuron,
Malathion, Mecarbam, Mervinphos, Mesulfenphos, Metaldehyde, Methacrifos, Methamido phos, Methidathion, Methiocarb, Methomyl, Metolcarb, Milbemectin, Monocrotophos, Moxidectin,
Naled, NC 184, M 25, Nitenpyram
Omethoate, Oxamyl, Oxydemethon M, Oxydeprofos,
Parathion A, parathion M, permethrin, phenthoate, phorate, phosalone, phosmet, Phosphamdon, phoxim, pirimicarb, pirimiphos M, Primiphos A, profenofos, promecarb, propaphos, propoxur, prothiofos, prothoate, pymetrozine, Pyrachlophos, Pyradaphenthion, Pyresmethrin, pyrethrum, Pyridaben, pyrimidifen, pyriproxifen,
Quinalphos,
RH 5992,
Salithion, Sebufos, Silafluofen, Sulfotep, Sulprofos,
Tebufenozid, Tebufenpyrad, Tebupinmphos, Teflubenzuron, Tefluthrin, Temephos, Terbam, Terbufos, Tetrachlorvinphos, Thiafenox, Thiodicarb, Thiofanox, Thiomethon, Thionazin, Thunngiensin, Tralathenethrononium, Tralomenhriazonium, Tralomenhrononium, Tralomenhrononium
Vamtdothion, XMC, Xylylcarb, YI 5301/5302, zetamethrin.

A mixture with other known active ingredients, such as herbicides or with Fertilizers and growth regulators are possible.

When used as fungicides, the active compounds as such, in the form of their Formulations or the use forms prepared from them such as ready-to-use Solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules be applied. The application is done in the usual way, e.g. B. by pouring, Spraying, spraying, scattering, dusting, foaming, brushing, etc.

It is also possible to use the active ingredients according to the ultra-low-volume method to apply or the active ingredient preparation or the active ingredient itself in the soil inject. The seeds of plants can also be treated.

In the treatment of parts of plants, the drug concentrations in the Application forms when used as fungicides varied over a wide range will. They are generally between 1 and 0.0001% by weight, preferably between 0.5 and 0.001%.

In seed treatment, when used as fungicides in general Active substance amounts from 0.001 to 50 g per kilogram of seed, preferably 0.01 to 10 g needed.

In the treatment of the soil, when used as fungicides, there are active ingredient concentrations trations from 0.00001 to 0.1 wt .-%, preferably from 0.0001 to 0.02% am Place of action required.

When used as insecticides and acaricides, the active compounds according to the invention can be present in their commercially available formulations and in the use forms prepared from the formulations in a mixture with other active compounds, such as insecticides, attractants, sterilants, acaricides, nematicides, fungicides, growth-regulating substances or herbicides. Insecticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms and others
The following connections are mentioned:
Acrinathrin, alphamethrin, betacyfluthrin, bifenthrin, Brofenprox, cis-resmethrin, clocythrin, cycloprothrin, cyfluthrin, cyhalothrin, cypermethrin, deitamethrin, esfen valerate, pyrenolate, pyridine, fluvalhrine, fluvalhrin, fluvalhrine, fenvalhrine, fenvalhrine, fenvalhrate, fluvalhrate, fenvalhrate, fluvalhrate, fenvalhrate, fluvalhrate, , Tralomethrin, zetamethrin,
Alanycarb, Bendiocarb, Benfuracarb, Bufencarb, Butocarboxim, Carbaryl, Cartap, Ethiofencarb, Fenobucarb, Fenoxycarb, Isoprocarb, Methiocarb, Methomyl, Metolcarb, Oxamyl, Pirimicarb, Promecarb, Propoxur, Terbam, Thiodicarb, Thacarbyox, Trim
Acephate, Azinphos A, Azinphos M, Bromophos A, Cadusafos, Carbophenothion, Chlorfenvinphos, Chlormephos, Chlorpyrifos, Chlorpyrifos M, Cyanophos. Demeton M, Demeton-S-methyl, Demeton S, Diazinon, Dichlorvos, Dicliphos, Dichlorfenthion, Dicrotophos, Dimethoate, Dimethylvinphos, Dioxathion, Disulfoton, Edifenphos, Ethion, Etrimphos, Fenitrothion, Fenthion, Fonophos, Isothophophos, Hepthosphate, Hepten Isoxathion, Phorate, Malathion, Mecarbam, Mervinphos, Mesulfenphos, Methacrifos, Methamidophos, Naled, Omethoate, Oxydemeton M, Oxydeprofos, Parathion A, Parathion M, Phenthoate, Phorate, Phosalone, Phosmet, Phosphamdon, Moxim, Pirimhos, Pirimos, Pirimos , Prothiophos, Prothoate, Pyraclophos, Pyridaphenthion, Quinalphos, Salithion, Sebufos, Sulfotep, Sulprofos, Tetrachlorvinphos, Temephos, Thiomethon, Thionazin, Trichlorfon, Triazophos, Vamidothion,
Buprofezin, chlorofiuazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, pyriproxifen, tebufenozide, teflubenzuron, triflumuron,
Imidacloprid, nitenpyram, N - [(6-chloro-3-pyridinyl) methyl] -N'-cyano-N-methyl-ethane-imidamide (NI-25),
Abamectin, Amitrazin, Avermectin, Azadirachtin, Bensuftap, Bacillus thurmgiensis, Cyromazine, Diafenthiuron, Emamectin, Ethofenprox, Fenpyrad, Fipronil, Flufenprox, Lufenuron, Metaldehyde, Milbemectin, Pymetrozad, Trebiazurpine
Aldicarb, Bendiocarb, Benfuracarb, Carbofuran, Carbosulfan, Chlorethoxyfos, Cloethocarb, Disulfoton, Ethophrophos, Etrimphos, Fenamiphos, Fipronil, Fonofos, Fosthiazate, Furathiocarb, HCH, Isazophos, Isofenphos, Phiophimoxox, Phiophosox, Phiophos, Monophyamate, Methiocarbam, Monophyamate, Methiocarbox, Methiocarbox, Methiocorox, Phi Pyrachlofos, Sebufos, Silafluofen, Tebupirimphos, Tefluthrin, Terbufos, Thiodicarb, Thiafenox,
Azocyclotin, Butylpyridaben, Clofentezine, Cyhexatin, Diafenthiuron, Diethion, Emamectin, Fenazaquin, Fenbutatin Oxide, Fenothiocarb, Fenpropathrin, Fenpyrad, Fenpyroximate, Fluazinam, Fluazuron, Flucycloxuron, Flufenoxuron, Methoxin, Oxoxinatex, Oxoxin, Oxoxin, Oxoxin, Oxoxin, Oxidoxin , Phosalones, Profenofos, Pyraclofos, Pyridaben, Pyrimidifen, Tebufenpyrad, Thuringiensin, Triarathene as well as 4-Bromo-2- (4-chlorophenyl) -1- (ethoxymethyl) -5- (trifluoromethyl) -1H-pyrrole-3-carbonitrile (AC 303630).

When used as insecticides and Acaricides also in their commercially available formulations and in those from them Formulations prepared use forms are available in a mixture with synergists. Synergists are compounds that increase the effectiveness of the active ingredients, without the added synergist itself having to be active.

The active substance content of the application prepared from the commercially available formulations molds when used as insecticides and acaricides in a wide range vary. The active ingredient concentration of the use forms can range from 0.0000001 to 95% by weight of active ingredient are preferably between 0.0001 and 1% by weight.

The agents used to protect technical materials contain the active ingredients generally in an amount of 1 to 95%, preferably 10 to 75%.

The application concentrations of the active compounds according to the invention depend on the type and the occurrence of the microorganisms to be controlled and according to the Composition of the material to be protected. The optimal amount can be used can be determined by test series. In general, the application concentrations in the range of 0.001 to 5% by weight, preferably from 0.05 to 1.0% by weight based on the material to be protected.  

The effectiveness and the spectrum of action of those which can be used according to the invention Active substances or the agents, concentrates or from them in general Formulations can be increased if necessary further antimicrobial active compounds, fungicides, bactericides, herbicides, insecticides or others Active substances to enlarge the spectrum of effects or to achieve special ones Effects such as B. added protection against insects. These Mixtures can have a broader spectrum of activity than the invention appropriate connections.

In many cases, synergistic effects are obtained, i. H. the effectiveness of Mixing is greater than the effectiveness of the individual components. Particularly cheap Mix partners are e.g. B. the following connections:

Sulfenamides such as dichlorfluanid (Euparen), tolyfluanid (Methyleuparen), Folpet, Fluorfolpet;
Benzimidazoles such as Carbendazim (MBC), Benomyl, Fuberidazole, Thiabendazole or their salts;
Thiocyanates such as thiocyanatomethylthiobenzothiazole (TCMTB), methylene bisthio cyanate (MBT);
quaternary ammonium compounds such as benzyldimethyltetradecylammonium chloride, benzyldimethyldodecylammonium chloride, dodecyldimethylammonium chloride;
Morpholine derivatives such as C₁₁-C₁₄-4-alkyl-2,6-dimethyl-morpholine homologue (tride morph), (±) -cis-4- [tert-butylphenyl) -2-methylpropyl] -2,6-dimethylmorpholine (fen propimorph ), Falimorp;
Phenols such as o-phenylphenol, tribromophenol, tetrachlorophenol, pentachlorophenol, 3-methyl-4-chlorophenol, dichlorophen, chlorophen or their salts;
Azoles such as triadimefon, triadimenol, bitertanol, tebuconazole, propiconazole, aza conazole, hexaconazole, prochloraz, cyproconazole, 1- (2-chlorophenyl) -2- (1-chlorocyclopropyl) -3- (1,2,4-triazol-1-) yl) prop-an-2-ol or 1- (2-chlorophenyl) -2- (1,2,4-triazol-1-yl-methyl) -3,3-dimethyl-butan-2-ol.
Iodopropargyid derivatives such as iodopropargyl butyl carbamate (IPBC), chlorophenyl formal, phenyl carbamate, hexyl carbamate, cyclohexyl carbamate, iodopropargyloxyethylphenyl carbamate;
Iodine derivatives such as diiodomethyl-p-arylsulfones e.g. B. Diiodomethyl-p-tolyl sulfone;
Bromine derivatives such as bromopol;
Isothiazolines such as N-methylisothiazolin-3-one, 5-chloro-N-methylisothiazolin-3-one, 4,5-dichloro-N-octylisothiazolin-3-one, N-octylisothlazolin-3-one (octilinone);
Benzisothiazolinones, cyclopentene isothazolines;
Pyridines such as 1-hydroxy-2-pyridinthione (and their Na, Fe, Mn, Zn salts), tetrachloro-4-methylsulfonylpyridine;
Metal soaps such as tin, copper, zinc naphthenate, octoate, -2-ethylhexanoate, oleate, phosphate, benzoate, oxides such as TBTO, Cu₂O, CuO, ZnO;
Organic tin compounds such as tributyltin naphtenate and tributyltin oxide;
Dialkyldithiocarbamates such as Na and Zn salts of dialkyldithiocarbamates, tetramethyltiuramide disulfide (TMTD);
Nitriles such as 2,4,5,6-tetrachloroisophthalonitrile (chlorothalonil), inter alia, microbicides with an activated halogen group such as Cl-Ac, MCA, tectamer, bromopol, bromidox;
Benzothiazo such as 2-mercaptobenzothiazoles; says Dazomet;
Quinolines such as 8-hydroxyquinoline;

Formaldehyde-releasing compounds such as benzyl alcohol mono (poly) hemiformal, oxazolidines, hexahydro-s-triazines, N-methylolchloroacetamide;
Tris-N- (cyclohexyldiazeniumdioxy) aluminum, N- (cyclohexyldiazeniumdioxy) -Tri butyltin or K salts, bis- (N-cyclohexyl) diazinium- (dioxy copper or aluminum).

The following are preferably added as insecticides:
Phosphoric acid esters such as azinphos-ethyl, azinphos-methyl, 1- (4-chlorophenyl) -4- (O-ethyl, S-propyl) phosphoryloxypyrazole (TIA-230), chlorpyrifos, Coumaphos, De meton, Demeton-S-methyl, diazinon , Dichlorfos, Dimethoate, Ethoprophos, Etrim fos, Fenitrothion, Fention, Heptenophos, Parathion, Parathion-methyl, Phosalone, Phoxim, Pirimiphos-ethyl, Pirimiphos-methyl, Profenofos, Prothiofos, Sulprofos, Triazophos and Trichlorphon.

Carbamates such as aldicarb, bendiocarb, BPMC (2- (1-methylpropyl) phenyl methyl carbamate), butocarboxime, butoxycarboxime, carbaryl, carbofuran, carbosul fan, cloethocarb, isoprocarb, methomyl, oxamyl, pirimicarb, promecarb, propoxur and thiodicarb.

Pyrethroids such as allethrin, alphamethrin, bioresmethrin, byfenthrin (FMC 54800), Cycloprothrin, cyfluthrin, decamethrione, cyhalothrin, cypermethrin, deltamethrin, Alpha-cyano-3-phenyl-2-methylbenzyl-2,2-dimethyl-3- (2-chloro-2-trifluoromethylvinyl) - cycloprppan carboxylate, fenpropathrin, fenfluthrin, fenvalerate, flucythrinate, Flumethrin, fluvalinate, permethrin and resmethrin; Nitroimino and nitromethylene compounds such as 1 - [(6-chloro-3-pyridinyl) methyl] -4,5-dihydro-N-nitro-1H-imida zol-2-amine (imidachloprid).

Organosilicon compounds, preferably dimethyl (phenyl) silylmethyl-3-phen oxybenzyl ether such as B. Dimethyl (4-ethoxyphenyl) silylmethyl 3-phenoxybenzyl ether  or dimethyl (phenyl) silylmethyl-2-phenoxy-6-pyridylmethyl ether such as e.g. B. Dimethyl (9-ethoxyphenyl) silylmethyl-2-phenoxy-6-pyridylmethyl ether or (Phe nyl) [3- (3-phenoxyphenyl) propyl] (dimethyl) silanes such as e.g. B. (4-Ethoxyphenyl) - [3 (4- fluoro-3-phenoxyphenyl) propyl] dimethylsilane.

Algicides, molluscicides, active substances against are considered as other active substances "sea animals" referring to e.g. B. Settling floor paints.

The production of active ingredients and their use according to the invention illustrated by the following examples.

Manufacturing examples Example 1

To 4.12 g (0.02 mol) of 2-hydroxy-4-trifluoromethylbenzoic acid and 2.91 g (0.02 mol) 3-chloro-4-fluoroaniline in 100 ml of toluene is slowly added 0.7 at the reflux temperature ml of phosphorus trichloride, and after the addition has ended, the mixture is stirred in for a further 16 hours Reflux. The reaction mixture is concentrated and the product is removed Isopropanol / water crystallized. 4.56 g (68% of theory) of 2-hydroxy-4- are obtained. trifluoromethylbenzoic acid 3-chloro-4-fluoroanilide with a melting point of 179 ° C.

Analogous to Example 1 and in accordance with the general description of the The inventive method are those in Table 1 below Compounds of formula (I) listed:

Table 1

Examples of use

In the following application examples, the following were listed Compounds used as reference substances:

2-hydroxy-4-trifluoromethyl-N- (4-isopropylphenyl) benzamide

2-hydroxy-4-trifluoromethyl-N- (3,4-dimethylphenyl) benzamide

2-hydroxy-4-trifluoromethyl-N- (3,5-dichlorophenyl) benzamide

2-hydroxy-4-trifluoromethyl-N- (3-chlorophenyl) benzamide

2-hydroxy-4-trifluoromethyl-N- (3-methylphenyl) benzamide

2-hydroxy-4-trifluoromethyl-N- (4-ethylphenyl) benzamide

2-hydroxy-4-trifluoromethyl-N- (3-bromophenyl) benzamide

2-hydroxy-4-trifluoromethyl-N- (3-chloro-4-methylphenyl) benzamide
(All known from WO-A 92/17066)

Example A Phytophthora test (tomato) / protectiv

Solvent: 4.7 parts by weight of acetone
Emulsifier: 0.3 part by weight of alkyl aryl polyglycol ether

To produce a suitable preparation of active compound, mix 1 Part by weight of active ingredient with the stated amounts of solvent and emulsifier and dilute the concentrate with water to the desired concentration.

To test for protective effectiveness, young plants are sprayed with the Active ingredient preparation to dripping wet. After the spray coating has dried on the plants with an aqueous spore suspension of Phytophthora inftstans inoculated.

The plants are grown in an incubation cabin with 100% relative humidity and set up at about 20 ° C.

Evaluation is carried out 3 days after the inoculation.

In this test, the compounds of Examples 1, 2, 5, 6, 7, 12, 13, 14, 15, 17, 19, 20, 21, 22, 25, 26, 27, 28, 29, 34, 38, 39, 41, 42, 48, 64, 66, 87, 94, 96, 97, 104 and 105 with an active ingredient concentration of 10 ppm an efficiency of 70% up to 100%, while the comparison substance (C) has an efficiency of 15% having.  

Example B Plasmopara test (vine) / protectiv

Solvent: 4.7 parts by weight of acetone
Emulsifier: 0.3 part by weight of alkyl aryl polyglycol ether

To produce a suitable preparation of active compound, mix 1 Part by weight of active ingredient with the stated amounts of solvent and emulsifier and dilute the concentrate with water to the desired concentration.

To test for protective effectiveness, young plants are sprayed with the Active ingredient preparation to dripping wet. After the spray coating has dried on inoculated the plants with an aqueous spore suspension of Plasmopara viticola and then stay in a humid chamber at 20-22 ° C and 100% relative for 1 day Humidity. The plants are then 5 days in a greenhouse at 21 ° C. and 90% humidity. The plants are then moistened and 1 Placed in a humidity chamber during the day.

Evaluation is carried out 6 days after the inoculation.

In this test, the compounds of Examples 1, 5, 6, 7, 11, 12, 13, 15, 17, 19, 20, 22, 25, 26, 27, 28, 29, 30, 37, 39, 42, 48, 49, 63, 75, 87, 88, 89, 90, 92, 94, 95, 96, 97, 98, 100, 101, 103, 104, 105, 106 and 107 for one Active ingredient concentration of 10 ppm an efficiency of 79% to 100%.  

Example C Pyricularia test (rice) / protectiv

Solvent: 12.5 parts by weight of acetone
Emulsifier: 0.3 part by weight of alkyl aryl polyglycol ether

To produce a suitable preparation of active compound, mix 1 Weight part of active ingredient with the specified amounts of solvent and diluted the concentrate with water and the specified amount of emulsifier on the desired concentration.

To test for protective effectiveness, young rice plants are sprayed with the Active ingredient preparation to dripping wet. After the spray coating has dried off the plants are moculated with an aqueous spore suspension of Pyricularia oryzae. Then the plants in a greenhouse at 100% relative Humidity and 25 ° C.

The disease infestation is evaluated 4 days after the inoculation.

In this test, the compounds of Examples 1, 4, 5, 7, 8, 11, 12, 13, 14, 18, 20, 22, 26, 34, 63, 99, 100, 104, 105 and 106 at an active ingredient concentration of 0.025 ppm an efficiency of 80% to 100%.  

Example D Plutella test

Solvent: 31 parts by weight of acetone
Emulsifier: 1 part by weight of alkyl aryl polyglycol ether

To produce a suitable preparation of active compound, mix 1 Weight part of active ingredient with the specified amount of solvent and specified amount of emulsifier and dilute the concentrate with emulsifier Water to the desired concentrations.

Cabbage leaves (Brassica oleracea) are mixed with the active ingredient preparation of the desired Concentration treated. A treated sheet is placed in the plastic can and with Larvae (L2) of the cockroach (Plutella xylostella) occupied. After 3 days each an untreated sheet is used for the refill.

After the desired time, the kill is determined in%. 100% means that all animals were killed; 0% means that no animals have been killed.

In this test, the compounds of Examples 47 and 78 show one Drug concentration of 0.01% after 7 days a degree of killing of 100%, while the comparison substances (A), (B), (C), (E) and (F) have no effect exhibit.  

Example E Tatranychus test (OP-resistant / diving treatment)

Solvent: 7 parts by weight of acetone
Emulsifier: 1 part by weight of alkyl aryl polyglycol ether

To produce a suitable preparation of active compound, mix 1 Weight part of active ingredient with the specified amount of solvent and specified amount of emulsifier and dilute the concentrate with emulsifier Water to the desired concentrations.

Bean plants (Phaseolus vulgaris), strongly of all stages of the common Spider mite Tetranychus urticae are infected in a drug preparation desired concentration immersed.

After the desired time, the effect is determined in%. 100% means that all spider mites have been killed; 0% means that there are no spider mites were killed.

In this test, the compounds of Examples 78, 98 and 103 show at one Drug concentration of 0.01% after 7 days a degree of killing of 80% to 100%, while the comparison substances (A), (B), (E) and (F) have no effect.  

Example F Phaedon larval test

Solvent: 7 parts by weight of dimethylformamide
Emulsifier: 1 part by weight of alkyl aryl polyglycol ether

To produce a suitable preparation of active compound, mix 1 Weight part of active ingredient with the specified amount of solvent and specified amount of emulsifier and dilute the concentrate with water to the desired concentrations.

Cabbage leaves (Brassica oleracea) are dipped into the active ingredient preparation the desired concentration and treated with horseradish leaf beetle larvae (Phaedon cochleariae) occupied while the leaves are still moist.

After the desired time, the kill is determined in%. 100% means that all beetle larvae have been killed; 0% means that there are no beetle larvae were killed.

In this test the compounds of Examples 34, 63 and 68 show at one Active ingredient concentration of 0.1% after 7 days a degree of killing of 100%, while the comparison substance (B) has no effect.  

Example G Plutella test

Solvent: 7 parts by weight of dimethylformamide
Emulsifier: 1 part by weight of alkyl aryl polyglycol ether

To produce a suitable preparation of active compound, mix 1 Weight part of active ingredient with the specified amount of solvent and specified amount of emulsifier and dilute the concentrate with water to the desired concentrations.

Cabbage leaves (Brassica oleracea) are dipped into the active ingredient preparation the desired concentration and treated with caterpillars (Plutella maculipennis) as long as the leaves are still moist.

After the desired time, the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.

In this test, the compounds of Examples 14, 20 and 63 show one Drug concentration of 0.1% after 7 days a degree of killing of 85% to 100%, while the comparison substance (B) has no effect.  

Example H Material protection test Inhibition test on giant colonies of Basidiomycetes

From colonies of Gloeophyllum trabeum, Coniophora puteana, Poria placenta, Lentinus tigrinus, Coriolus versicolor and Stereum sanguinolentum were Mycelium pieces are cut out and placed on an agar medium containing malt extract and peptone incubated at 26 ° C. The inhibition of hyphal growth on active ingredients Culture media became with the length growth on culture medium without active ingredient addition compared and rated as a percentage inhibition.

In this test, the compounds according to the invention from Examples 1, 3, 17, 34, 38 and 92, inhibiting growth at an active substance concentration of 20 ppm from 50 to 100%.

Claims (9)

1. 4-trifluoromethylbenzamides of the formula (I), in which
Ar represents substituted phenyl,
except for the meanings:
3-chlorophenyl; 3-bromophenyl; 3-methylphenyl; 3-trifluoromethyl phenyl; 4-chlorophenyl; 4-methoxyphenyl; 4-trifluoromethylphenyl; 4- (C₁-C₃) alkylphenyl; 3,5-dichlorophenyl; 3-chloro-4-methylphenyl and 3,4-dimethylphenyl. 2. Compounds of the formula (III) in which
R¹, R², R³ and R⁴ are independently hydrogen, halogen, cyano, nitro; each straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 6 carbon atoms; each straight-chain or branched haloalkyl, haloalkoxy or haloalkylthio each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms;
each straight-chain or branched alkoxycarbonyl or alkoximino alkyl each having 1 to 4 carbon atoms in the individual alkyl parts; Amino, aminocarbonyl; in each case straight-chain or branched alkyl amino, alkylaminocarbonyl, dialkylamino or dialkylaminocarbonyl each having 1 to 4 carbon atoms in the individual alkyl parts; each straight-chain or branched alkenyl, alkenyloxy or alkenylthio each having 2 to 4 carbon atoms; and optionally optionally up to three times, identical or different, substituted by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms, phenyl, where at least one of the radicals R¹, R², R³ and R⁴ is not hydrogen and with the exception of the compounds:
3-chlorophenyl; 3-bromophenyl; 3-methylphenyl; 3-trifluoromethyl phenyl; 4-chlorophenyl; 4-methoxyphenyl; 4-trifluoromethylphenyl; 4- (C₁-C₃) alkylphenyl; 3,5-dichlorophenyl; 3-chloro-4-methylphenyl and 3,4-dimethylphenyl. 3. Compounds of formula (III) according to claim 2,
in which
R¹, R², R³ and R⁴ independently represent hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, n- or i-propyl; n-, i-, s- or t-butyl; n-, i-, s- or t-pentyl; Methoxy, ethoxy, n- or i-propoxy; n-, i-, s- or t-butoxy; Methylthio, ethylthio, n- or i-propylthio; n-, i-, s- or t-butylthio; Trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, difluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, methoximinoethyl, ethoximino methyl, ethoximinoethyl;
Amino, aminocarbonyl, methylamino, ethylamino, n- or i-propyl amino, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propyl aminocarbonyl, dimethylamino, ethylmethylamino, methyl-n-propylamino, methyl-i-propylamino, diethylamino, dimethylaminocarbonocarbonyl, ethylmethylamin , Methyl-n-propylaminocarbonyl, methyl-i-propylaminocarbonyl, diethylaminocarbonyl, propenyl, butenyl, isobutyl, propenyloxy, butenyloxy, isobutenyloxy, propenylthio, butenylthio, isobutenylthio;
or optionally phenyl substituted one to three times, identically or differently by fluorine, chlorine, bromine, methyl and / or ethyl, where at least one of the radicals R¹, R², R³ and R⁴ is not hydrogen and with the exception of the compounds:
3-chlorophenyl; 3-bromophenyl; 3-methylphenyl; 3-trifluoromethyl phenyl; 4-chlorophenyl; 4-methoxyphenyl; 4-trifluoromethylphenyl; 4- (C₁-C₃) alkylphenyl; 3,5-dichlorophenyl; 3-chloro-4-methylphenyl and 3,4-dimethylphenyl. 4. Compounds of formula (III) according to claim 2
in which
R¹, R², R³ and R⁴ independently represent hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, n- or i-propyl; n-, i-, s- or t-butyl; n-, i-, s- or t-pentyl; Methoxy, ethoxy, n- or i-propoxy; n-, i-, s- or t-butoxy; Methylthio, ethylthio, n- or i-propylthio; n-, i-, s- or t-butylthio; Trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, difluoromethylthio, methoxycarbonyl, ethoxycarbonyl;
Methylamino, ethylamino, methylaminocarbonyl, ethylaminocarbonyl, dimethylamino, ethylmethylamino, diethylamino, dimethylamino carbonyl, ethylmethylaminocarbonyl, diethylaminocarbonyl, propenyloxy, butenyloxy, isobutenyloxy, propenylthio, butenylthio or r¹¹, R³ is not at least one of, r¹¹ and r¹³, R³ is not hydrogen, R³ is hydrogen or isobutenylthio; and excluding the connections:
3-chlorophenyl; 3-bromophenyl; 3-methylphenyl; 3-trifluoromethyl phenyl; 4-chlorophenyl; 4-methoxyphenyl; 4-trifluoromethylphenyl; 4- (C₁-C₃) alkylphenyl; 3,5-dichlorophenyl; 3-chloro-4-methylphenyl and 3,4-dimethylphenyl. 5. pesticide, characterized by a content of at least one compound of formula (I) according to claim 1.   6. A method for controlling pests, characterized in that Compounds of formula (I) according to claim 1 on pests and / or their Living space. 7. Use of compounds of the formulas (I) and (III) according to the Claims 1 to 4 for controlling pests. 8. Process for the preparation of pesticides, thereby characterized in that compounds of the formulas (I) or (III) according to the Claims 1 to 4 with extenders and / or surface-active agents mixed. 9. Process for the preparation of 4-trifluoromethylbenzamides of the formula (I), in which
Ar has the meaning given in claim 1,
characterized in that 2-hydroxy-4-trifluoromethylbenzoic acid or its esters of the formula (II), in which
R represents hydrogen or alkyl,
with anilines of the formula (III), H₂N-Ar (III) in which
Ar has the meaning given above,
in the presence of a condensing agent and optionally in the presence of a diluent and a reaction auxiliary.