WO1996005170A1

WO1996005170A1 - 4-trifluoromethylbenzamides and their use as pesticides in plant and materials protection

Info

Publication number: WO1996005170A1
Application number: PCT/EP1995/003026
Authority: WO
Inventors: Dietmar Kuhnt; Michael Haug; Klaus Jelich; Klaus Stenzel; Heinz-Wilhelm Dehne; Gerd Hänssler; Ulrike Wachendorff-Neumann; Christoph Erdelen; Martin Kugler; Heinrich Schrage
Original assignee: Bayer Aktiengesellschaft
Priority date: 1994-08-11
Filing date: 1995-07-31
Publication date: 1996-02-22
Also published as: DE4428380A1; AU3382295A

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

-Trifluoromethylbenzamides and their use as pesticides in plant and material protection

The invention relates to new 4-trifluoromethylbenzene, a process for their preparation and their use as pesticides in crop protection 10 and in material protection.

It is known that certain 4-trifluoromethylbenzamides, such as, for example, the 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 15 92/17066).

However, the effectiveness of these previously known compounds is not entirely satisfactory in all fields of application, especially when low application rates are involved.

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

20 in which

Ar represents substituted phenyl, _^ , _{n *} .χ _mn 96/05170

except for the meanings:

3-chlorophenyl; 3-bromophenyl; 3-methylphenyl; 3-trifluoromethylphenyl; 4-chlorophenyl; 4-methoxyphenyl; 4-trifluoromethylphenyl; 4- (Cι-C3) alkylphenyl; 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

5 R represents hydrogen or alkyl,

with anilines of the formula (III),

H _j N -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. They are characterized in particular by strong microbicidal properties both in crop protection and in material protection, and by high insecticidal and acaricidal activity.

Surprisingly, the 4-trifluoromethylbenzamides of the formula (I) according to the invention show a better activity than the constitutionally most similar previously known compounds.

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

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

a)

in which

Rl for halogen, cyano, nitro; each straight-chain or branched alkyl, alkoxy or alkylthio, each with 1 to 6 cobien 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 alkylamino, alkylaminocarbonyl, dialkylamino or dialkylaminocarbonyl each having 1 to 4 carbon atoms in the individual alkyl parts; each 170

- 4 -

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.

b)

in which

R- 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 alkylamino, 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 mono- to trisubstituted, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms

Phenyl stands. 5 -

c)

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 alkylamino, 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 mono- to trisubstituted, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms

Phenyl stands.

d)

in which

Arl for the groupings stands,

wherein Rl, R-, R- and R ^ are the same or different and 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 alkylamino, 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 and R ^ 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.

e)

in which

R- 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 a ino, 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

R ^ 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; Halogenalkoxy 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 alkylamino, 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

R- 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

Amino, aminocarbonyl; in each case straight-chain or branched alkylamino, 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

R ⁴ for halogen, cyano, nitro; straight-chain or branched alkyl having 2 to 6 carbon atoms; each straight-chain or branched alkoxy or

Aklylthio, each with 1 to 6 carbon atoms; each straight-chain or branched haloalkyl; Halogenalkoxy or haloalkylthio with each 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 alkylamino, 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

R- for fluorine, bromine, iodine, cyano, nitro; straight-chain or branched alkyl having 2 to 6 carbon atoms; each straight-chain or branched

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 alkylamino, 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

R ^{4 represents} methyl; or

R ⁴ and R ⁴ 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.

G)

in which

Ar2 for the groupings

where R \, R-, R * and R ^{4 are} identical 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 alkylamino, 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 R ^ and R ^ or R ^ and R ⁴ or R- and R ⁴ 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 (Ig) are particularly preferred: a)

in which

R * 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, methoximinoethyl, ethoximinomethyl, ethoximinoethyl;

Amino, aminocarbonyl, methylamino, ethylamino, n- or i-propylamino, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylamino, ethylmethylamino, methyl-n-propylamino, methyl-i-propylamino, diethylamino, Dimethylaminocarbonyl, ethylmethylaminocarbonyl, 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. 05170

- 12th

b)

in which

R ^ for 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, ethoximinoethyl;

Amino, aminocarbonyl, methylamino, ethylamino, n- or i-propylamino, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylamino, ethylmethylamino, methyl-n-propylamino, methyl-i-propylamino, diethylamino, Dimethylaminocarbonyl, ethylmethylaminocarbonyl, methyl-n-propyl-aminocarbonyl, 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.

c)

in which

R ⁴ 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, methoximinoethyl, ethoximinomethyl, ethoximinoethyl; Amino, aminocarbonyl, methylamino, ethylamino, n- or i-propylamino, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylamino, ethylmethylamino, methyl-n-propylamino, methyl-i-propylamino, diethylamino, Dimethylaminocarbonyl, ethylmethylaminocarbonyl, 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.

d)

in which

Ar * for the groupings

stands,

where R *, R-, R3 and R ^{4 are the} same or different and 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, 170

- 14

Ethoxycarbonyl, methoximinomethyl, methoximinoethyl, ethoximino-methyl, ethoximinoethyl;

Amino, aminocarbonyl, methylamino, ethylamino, n- or i-propylamino, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylamino, ethylmethylamino, methyl-n-propylamino, methyl-i-propylamino, diethylamino, Dimethylaminocarbonyl, ethylmethylaminocarbonyl, 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 Rl and R- together represent methylenedioxo, ethylenedioxo, difluoromethylenedioxo or tetrafluoroethylene dioxo. e)

in which

R- 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, methoximinoethyl, ethoximinomethyl, ethoximinoethyl; Amino, aminocarbonyl, methylamino, ethylamino, n- or i-propylamino, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylamino, ethylmethylamino, methyl-n-propylamino, methyl-i-propylamino, diethylamino, Dimethylaminocarbonyl, ethylmethylaminocarbonyl, methyl-n-propyl-aminocarbonyl, 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

R ^{3 is} 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,

Amino, aminocarbonyl, methylamino, ethylamino, n- or i-propylamino, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylamino, ethylmethylamino, methyl-n-propylamino, methyl-i-propylamino, diethylamino, Dimethylaminocarbonyl, ethylmethylaminocarbonyl, 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

R- 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, methoximinoethyl, ethoximinomethyl, ethoximinoethyl; Amino, aminocarbonyl, methylamino, ethylamino, n- or i-propylamino, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylamino, ethylmethylamino, methyl-n-propylamino, methyl-i-propylamino, diethylamino, Dimethylaminocarbonyl, ethylmethylaminocarbonyl, 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

R ^{4 is} 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, methoximinoethyl, ethoximinomethyl, ethoximinoethyl;

Amino, aminocarbonyl, methylamino, ethylamino, n- or i-propylamino, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylamino, ethylmethylamino, methyl-n-propylamino, methyl-i-propylamino, diethylamino, Dimethylaminocarbonyl,

Ethylmethylaminocarbonyl, methyl-n-propylaminocarbonyl, methyl-i-propylaminocarbonyl, diethylaminocarbonyl, propenyl, butenyl, isobutyl, propenyloxy, butenyloxy, isobutenyloxy, propenylthio, butenylthio, isobutenylthio; or optionally one to three times, identical or different by fluorine,

Chlorine, bromine, methyl and / or ethyl substituted phenyl;

or - 17th

R- for 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-propylamino, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylamino, ethylmethylamino, methyl-n-propylamino, methyl-i-propylamino, diethylamino, Dimethylaminocarbonyl, ethylmethylaminocarbonyl, 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

R ^{4 represents} methyl;

or

R ^ and R ⁴ together represent methylenedioxo, ethylenedioxo, difluoromethylenedioxo or tetrafluoroethylene dioxo. G)

in which

Ar2 for the groupings stands,

where R, R-, R- and R ^{4 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-propylamino, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylamino, ethylmethylamino, methyl-n-propylamino, methyl-i-propylamino, diethylamino, Dimethylaminocarbonyl, ethylmethylaminocarbonyl, 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

R ^ and R- or R ^ and R ⁴ or R ³ and R ⁴ together represent methylenedioxo, ethylenedioxo, difluoromethylenedioxo or tetrafluoroethylene dioxo. The following groups of substances (a) to (g) of the formulas (Ia) to (Ig) are very particularly preferred: a)

in which

Rl 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, dimethylaminocarbonyl, ethylmethylaminocarbonyl, diethylaminocarbonyl, propenyloxy, butenyloxy, isobutenyloxy, propenylthio, butenylthio or isobutenylthio. b)

in which

R ^ for 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; 5170

- 20 -

Methylamino, ethylamino, methylaminocarbonyl, ethylaminocarbonyl, dimethylamino, ethylmethylamino, diethylamino, dimethylaminocarbonyl, ethylmethylaminocarbonyl, diethylaminocarbonyl, propenyloxy, butenyloxy, isobutenyloxy, propenylthio, butenylthio or isobutenylthio. c)

in which

R ⁴ 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, dimethylaminocarbonyl, ethylmethylaminocarbonyl, diethylaminocarbonyl, propenyloxy, butenyloxy, isobutenyloxy, propenylthio, butenylthio or isobutenylthio. d)

in which

Arl for the groupings

W // R "

stands,

R ³ 5170

21 -

wherein Rl, R-, R ³ and R ^{4 are the} same or different and 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, dimethylaminocarbonyl, ethylmethylaminocarbonyl, diethylaminocarbonyl, propenyloxy,

Butenyloxy, isobutenyloxy, propenylthio, butenylthio or isobutenylthio; or Rl and R- together represent methylenedioxo, ethylenedioxo, Difluor¬ methylenedioxo or tetrafluoroethylene dioxo. e)

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, dimethylaminocarbonyl, ethylmethylaminocarbonyl, diethylaminocarbonyl, propenyloxy, butenyloxy, isobutenyloxy, propenylthio, butenylthio and isobutenylthio R ^{3 is} 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, dimethylaminocarbonyl, ethylmethylaminocarbonyl, diethylaminocarbonyl, propenyloxy, butenyloxy, isobutenyloxy, propenylthio, butenylthio or isobutenylthio.

in which

R- 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, dimethylaminocarbonyl, ethylmethylaminocarbonyl, diethylaminocarbonyl, propenyloxy, butenyloxy, isobutenyloxy, propenylthio, butenylthio and isobutenylthio

R ^{4 is} 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, dimethylaminocarbonyl, 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

R- for 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,

Butenyloxy, isobutenyloxy, propenylthio, butenylthio or isobutenylthio and

R ^{4 represents} methyl;

or

R2 and R ⁴ together represent methylenedioxo, ethylenedioxo, difluoromethylenedioxo or tetrafluoroethylene dioxo. 5170

- 24th

G)

in which

Ar ² for the groupings

stands,

where Rl, R-, R ³ and R ^{4 are the} same or different and 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, dimethylaminocarbonyl, ethylmethylaminocarbonyl, diethylaminocarbonyl, propenyloxy,

Butenyloxy, isobutenyloxy, propenylthio, butenylthio or isobutenylthio;

or

R ^ and R ² or R- and R ⁴ or R ³ and R ⁴ together represent methylenedioxo, ethylenedioxo, difluoromethylenedioxo or tetrafluoroethylenedioxo. If, for example, 2-hydroxy-4-trifluoromethylbenzoic acid and 3-chloro-4-fluoroaniline are used as starting materials, the course of the reaction of the process according to the invention can be represented by the following formula:

Formula (IT) provides a general definition of the 2-hydroxy-4-trifluoromethylbenzoic acid required as the starting material for carrying out the process according to the invention, or the esters thereof. In this formula, R preferably represents hydrogen or straight-chain or branched alkyl having 1 to 4 carbon atoms. The 2-hydroxy-4-trifluoromethylbenzoic acid or its esters are known (cf. e.g. WO-A 92/17066).

Formula (HI) provides a general definition of the anilines which are also required as starting materials for carrying out the process according to the invention. In this formula, Ar preferably or particularly preferably has those meanings which have already been given above in connection with the description of the compounds of the formula (I) as preferred or particularly preferred for these substituents. The anilines of the formula (HT) are generally known compounds of organic chemistry.

The process according to the invention is carried out in the presence of a suitable condensing agent. As such, all condensation agents which can usually be used for such amidation reactions are suitable. Acid halide formers such as phosphorus tribromide, phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride or thionyl chloride may be mentioned as examples; Anhydride formers such as ethyl chloroformate or methanesulfonyl chloride; Carbodiimides, such as N, N'-dicyclohexylcarbodiimide (DCC) or other customary condensing agents, such as N, N'-carbonyldiimidazole, 2-ethoxy-N-ethoxycarbonyl-l, 2-dihydroquinoline (EEDQ) or triphenylphosphine / carbon tetrachloride. Inert organic solvents are suitable as diluents for carrying out the process according to the invention. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, 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-methylformane, N-methylpyrroudone 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. All conventional inorganic or organic bases are suitable as such. These include, for example, alkaline earth metal 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 or ammonium acetate such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, pyridine, N-methylpiperidine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicycloundecene (DBU).

The reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, 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, generally 1.0 to 2.0 mol, preferably 1.0 to 1.3 mol, of aniline of the formula are used per mole of 2-hydroxy-4-trifluoromethylbenzoic acid or its ester of the formula (II) (III), 0.3 to 5.0 moles, preferably 0.5 to 2.0 moles, of condensing agent and optionally 0 to 5.0 moles, preferably 0 to 2.5 moles, of as reaction auxiliary base used. The reaction is carried out, worked up and isolated by known processes.

The active compounds of the formula (I) according to the invention have a strong action against pests and can be used practically to combat unwanted harmful organisms. The active ingredients are suitable for use as fungicides in crop protection and in material protection. In addition, the active compounds according to the invention are suitable for controlling animal pests.

Fungicides are used in crop protection to combat Plasmodiophoromvcetes. Oomvcetes. Chvtridiomvcetes. Zvgomvcetes. Ascomvcetes. Basidiomvcetes and Deuteromvcetes.

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 fact that the active compounds are well tolerated by plants in the concentrations required to combat plant diseases allows treatment of above-ground parts of plants, of propagation stock and seeds, and of the soil.

The active compounds according to the invention can be used with particularly good results to combat diseases in fruit and vegetable production, such as, for example, against the pathogen causing tomato brown rot (Phytophthora infestans) or against the pathogen causing downy mildew on vines (Plasmopara viticola) or for combating cereal diseases, such as For example, against the pathogen causing brown furs in wheat (Septoria nodorum) or against the pathogen causing brown spot disease on barley or wheat (Cochliobolus sativus) or against the pathogen causing net spot disease on barley (Pyrenophora teres) or for combating rice diseases, such as against Rice stain pathogen (Pyricularia oryzae) or against the rice stem disease (Pellicularia sasakii).

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 controlling animal pests, preferably arthropods and nematodes, in particular insects and arachnids, which occur in agriculture, in forests, in the protection of vegetation and materials and in the hygiene sector. They are effective against normally sensitive and resistant species as well as against all or individual stages of development. The pests mentioned above include: 5170

- 29 -

From the order of the Isopoda e.g. Oniscus asellus, Armadillidium vulgare, Porcellio scaber.

From the order of the Diplopoda e.g. Blaniulus guttulatus. From the order of the Chilopoda e.g. Geophilus carpophagus, S cutiger a spec. From the order of the Symphyla e.g. S cutiger ella immaculata. From the order of the Thysanura e.g. Lepisma saccharina. From the order of the Collembola e.g. Onychiurus armatus.

From the order of the Orthoptera e.g. Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella geπnanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentiaüs, Schistocerca gregaria. From the order of the Deπnaptera e.g. Forficula auricularia. From the order of the Isoptera e.g. Reticulitermes spp ..

From the order of the anoplura e.g. Phylloxera vastatrix, Pemphigus spp., Pediculus humanus corporis, Haematopinus spp., Linognathus spp. From the order of the Mallophaga e.g. Trichodectes spp., Damalinea spp.

From the order of the Thysanoptera e.g. Hercinothrips femoralis, Thrips tabaci.

From the order of the Heteroptera e.g. Eurygaster spp., Dysdercus intermedius,

Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.

From the order of the Homoptera e.g. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Phorodoniphascei, spp. Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. Psylla spp.

From the order of the Lepidoptera, for example 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., Trichoplocapsia n. , Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, 51

- 30 -

Tineola bisselliella, Tinea pellionella, Hofmannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura fümiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana. From the order of the Coleoptera e.g. Anobium punctatum, Rhizopertha dominica, Acanthoscelides obtectus, Bruchidius obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephuspp sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogodeπna spp., Anthrenus spp., Attagenus spp., Lyctus spp., Mehgethes aeneus, Ptinus spp., Niptus hololeucus spp., Gibbium , Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica. From the order of the Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.

From the order of the Diptera e.g. Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calüphora erythrocephala, Lucüia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomox 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 e.g. Xenopsylla cheopis, Ceratophyllus spp .. From the order of the Arachnida e.g. Scorpio maurus, Latrodectus mactans. From the order of the Acarina e.g. Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp.,. Chori ., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp ..

The plant parasitic nematodes include Pratylenchus spp., Radopholus simiüs, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp. 5170

- 31 -

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

The active compounds according to the invention can also be used to protect technical materials against attack and destruction by undesired microorganisms.

In the present context, technical materials are to be understood as non-living materials that have been prepared for use in technology. For example, technical materials which are to be protected against microbial change or destruction by active substances according to the invention can be adhesives, glues, papers and cardboard, textiles, leather, wood, paints and plastic articles, cooling lubricants and other materials which are attacked or decomposed by microorganisms can be. In the context of the materials to be protected, parts of production systems, for example cooling water circuits, which may be impaired by the multiplication of microorganisms, may also be mentioned. Within the scope of the present invention, technical materials are preferably adhesives, glues, papers and cartons, leather, wood, paints, cooling lubricants and heat transfer fluids, particularly preferably wood.

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

Bacteria, fungi, yeasts, algae and mucilaginous organisms may be mentioned as microorganisms which can bring about a degradation or a change in the technical materials. The active compounds according to the invention preferably act against fungi, in particular mold, wood-discoloring and wood-destroying fungi (Basidiomycetes) and against slime organisms and algae.

For example, microorganisms of the following genera may be mentioned: Alternaria, such as Altemaria 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; Trichodeπna, such as Trichoderma viride;

Escherichia, such as Escherichia coli;

Pseudomonas, such as Pseudomonas aeruginosa;

Staphylococcus, such as Staphylococcus aureus.

Depending on the field of application, the active ingredients can be converted into customary formulations, depending on their respective physical and / or chemical properties, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine encapsulations in polymeric substances and in Envelopes for seeds, as well as ULV cold and warm mist formulations.

These formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate 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. organic solvents, such as alcohols, can also be used as auxiliary solvents. The following are essentially suitable as liquid solvents: 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. Petrol or other 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; Liquefied gaseous extenders or carriers mean liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellants, such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide; Solid carrier materials are suitable: for example natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates; Solid carriers for granules are possible: for example broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; Possible emulsifiers and / or foam-generating agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; The following may be used as dispersants: for example lignin sulfite waste liquor and methyl cellulose.

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

Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue 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 in general contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.

When used as fungicides as such or in their formulations, the active compounds according to the invention can also be used in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides, in order, for example, to do this Spectrum of effects to spread or prevent development of resistance. In many cases, synergistic effects are obtained, ie the effectiveness of the mixture is greater than the effectiveness of the individual components.

Particularly cheap mixing partners are e.g. 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) methoximino [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, cyprofüram, dichlorophene, diclobutrazole, diclofluanide, diclomezin, dicloran, diethofencarb,

Difenoconazole, dimethirimol, dimethomorph, diniconazole, dinocap, diphenylamine,

Dipyrithion, Ditalimfos, Dithianon, Dodine, Drazoxolon,

Edifenphos, epoxyconazole, ethirimol, etridiazole,

Fenarimol, Fenbuconazole, Fenfüram, Fenitropan, Fenpiclonil, Fenpropidin, Fenpropimoφh, Fentinacetat, Fentinhydroxyd, Ferbam, Ferimzone, Fluazinam,

Fludioxonil, fluoromide, fluquinconazole, flusilazole, flusulfamide, flutolanil,

Flutriafol, folpet, fosetyl aluminum, fthalides, fuberidazole, furalaxyl, furmecyclox,

Guazatine, 5170

- 35 -

Hexachlorobenzene, hexaconazole, hymexazole,

Imazalil, Imibenconazol, Iminoctadin, Iprobefos (IBP), Iprodione, Isoprothiolan,

Kasugamycin, copper preparations, such as: copper hydroxide, copper naphthenate,

Copper oxychloride, copper sulfate, copper oxide, oxin-copper and Bordeaux mixture, Mancopper, Mancozeb, Maneb, Mepanipyrim, Mepronil, Metalaxyl, Metconazol,

Methasulfocarb, methfuroxam, metiram, metsulfovax, myclobutanil,

Nickel dimethyldithiocarbamate, nitrothal isopropyl, Nuarimol,

Ofrace, oxadixyl, oxamocarb, oxycarboxin,

Pefürazoate, penconazole, pencycuron, phosdiphen, pimaricin, piperahn, polyoxin, probenazole, prochloraz, procymidon, propamocarb, propiconazole, propineb,

Pyrazophos, Pyrifenox, Pyrimethanil, Pyroquilon,

Quintozen (PCNB),

Sulfur and sulfur preparations,

Tebuconazole, Tecloftalam, Tecnazen, Tetraconazole, Thiabendazole, Thicyofen, Thiophanat-methyl, Thiram, Tolclophos-methyl, Tolylfluanid, Triadimefon,

Triadimenol, triazoxide, trichlamide, tricyclazole, tridemorph, triflumizole, triforin,

Triticonazole,

Validamycin A, vinclozolin,

Zineb, Zira

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, Azocyclotin,

Bacillus thuringiensis, Bendiocarb, Benfuracarb, Bensultap, Betacyluthrin, Bifenthrin, BPMC, Brofenprox, Bromophos A Bufencarb, Buprofezin, Butocarboxin, Butylpyridaben, Cadusafos, Carbaryl, Carbofüran, Carbophenothion, Carbosulfan, Cartap, CGA 157 419,

CGA 184699, chloethocarb, chlorethoxyfos, chlorfenvinphos, chlorfluazuron,

Chlormephos, Chlorpyrifos, Chlorpyrifos M, Cis-Resmethrin, Clocythrin, Clofentezin,

Cyanophos, Cycloprothrin, Cyfluthrin, Cyhalothrin, Cyhexatin, Cypermethrin, Cyromazin, Deltamethrin, Demeton M, Demeton S, Demeton-S-methyl, Diafenthiuron, Diazinon,

Dichlofenthion, dichlorvos, dicliphos, dicrotophos, diethion, diflubenzuron, dimethoate,

Dimethylvinphos, dioxathione, disulfoton,

Edifenphos, Emamectin, Esfenvalerat, Ethiofencarb, Ethion, Ethofenprox, Ethoprophos,

Etrimphos, Fenamiphos, Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb,

Fenoxycarb, fenpropathrin, fenpyrad, fenpyroximate, fenthion, fenvalerate, fipronü,

Fluazinam, flucycloxuron, flucythrinate, flufenoxuron, flufenprox, fluvalinate, fonophos,

Formothion, Fosthiazat, Fubfenprox, Furathiocarb,

HCH, Heptenophos, Hexaflumuron, Hexythiazox, Imidacloprid, Iprobefos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Ivemectin,

Lamda-cyhalothrin, Lufenuron,

Malathion, Mecarbam, Mervinphos, Mesulfenphos, Metaldehyde, Methacrifos, Methamidophos, Methidathion, Methiocarb, Methomyl, Metolcarb, Milbemectin, Monocrotophos,

Moxidectin, Naled, NC 184, NI 25, Nitenpyram

Omethoate, Oxamyl, Oxydemethon M, Oxydeprofos,

Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet,

Phosphamdon, Phoxim, Pirimicarb, Pirimiphos M, Primiphos A, Profenofos, Promecarb,

Propaphos, Propoxur, Prothiofos, Prothoat, Pymetrozin, Pyrachlophos, Pyradaphenthion, Pyresmethrin, Pyrethrum, Pyridaben, Pyrimidifen, Pyriproxifen,

Quinalphos,

RH 5992,

Salithion, Sebufos, Silafluofen, Sulfotep, Sulprofos,

Tebufenozid, Tebufenpyrad, Tebupirimphos, Teflubenzuron, Tefluthrin, Temephos, Terbam, Terbufos, Tetrachlorvinphos, Thiafenox, Thiodicarb, Thiofanox, Thiomethon

Thionazin, Thuringiensin, Tralomethrin, Triarathen, Triazophos, Triazuron, Trichlorfon

Triflumuron, trimethacarb,

Vamidothion, XMC, Xylylcarb, YI 5301/5302, Zeta ethrin. A mixture with other known active ingredients, such as herbicides or with fertilizers and growth regulators, is also possible.

When used as fungicides, the active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules. They are used in the usual way, e.g. by pouring, spraying, spraying, scattering, dusting, foaming, brushing, etc.

It is also possible to apply the active ingredients using the ultra-low-volume process or to inject the active ingredient preparation or the active ingredient into the soil itself. The seeds of plants can also be traded.

In the treatment of parts of plants, the active compound concentrations in the use forms can be varied within a wide range when used as fungicides. They are generally between 1 and 0.0001% by weight, preferably between 0.5 and 0.001%.

In seed treatment, when used as fungicides, amounts of active ingredient of 0.001 to 50 g per kilogram of seed, preferably 0.01 to 10 g, are generally required.

When treating the soil, when used as fungicides, active ingredient concentrations of 0.00001 to 0.1% by weight, preferably 0.0001 to 0.02%, are required at the site of action.

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, Deltamethrin, Esfenvalerate, Etofenprox, Fenpropathrin, Fenvalerate, Flucythrinate, Fluvalinate, Lambda-Cyhalothrin, Permethrin, Pyresmethrin, Silethrin, Pyrethrin, Pyrethrin, Pyrethrin

Alanycarb, Bendiocarb, Benfuracarb, Bufencarb, Butocarboxim, Carbaryl, Cartap, Ethiofencarb, Fenobucarb, Fenoxycarb, Isoprocarb, Methiocarb, Methomyl, Metolcarb, Oxamyl, Pirimicarb, Promecarb, Propoxur, Terbam, Thiodicarb, Aiarbyx, Carboc 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, Pirimiphos Prothiophos, Prothoate, Pyraclophos, Pyridaphenthion, Quinalphos, Sahthion, Sebufos, Sulfotep, Sulprofos, Tetrachlorvinphos, Temephos, Thiomethon, Thionazin, Trichlorfon, Triazophos, Vamidothion,

Buprofezin, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, pyriproxifen, tebufenozide, teflubenzuron, triflumuron,

Imidacloprid, nitenpyram, N - [(6-chloro-3-pyridinymethyll-N'-cyano-N-methyl-ethanimidamide (NI-25), abamectin, amitrazine, avermectin, azadirachtin, bensultap, bacillus thuringiensis, cyromazine, Diafenthiuron, Emamectin, Ethofenprox, Fenpyrad, Fipronil, Flufenprox, Lufenuron, Metaldehyde, Milbemectin, Pymetrozine, Tebufenpyrad, Triazuron, Aldicarb, Bendiocarb, Benfuracarbos, Clofurosophos, Ephofosulfos, Ephofosulfos, Ephonophos, Ephonophos, Ephonophosphate, Fifronil, Ephonophosphate, Fifronil, Fifronil, Fifronil, Fifronil, Fifronil, Fifronil, Fifronophos, Fifronophos, Fifronophos, Fifronophos, Fifronos Fosthiazate, Furathiocarb, HCH, Isazophos, Isofenphos, Methiocarb, Monocrotophos, Nitenpyram, Oxamyl, Phorate, Phoxim, Prothiofos, Pyrachlofos, Sebufos, Silafluofen, Tebupirimphos, Tefluthrin, Terbufos, Thiodic

Azocyclotin, Butylpyridaben, Clofentezine, Cyhexatin, Diafenthiuron, Diethion, Emamectin, Fenazaquin, Fenbutatin Oxide, Fenothiocarb, Fenpropathrin, Fenpyrad, Fenpyroximate, Fluazinam, Fluazuron, Flucycloxuron, Flufenoxuron, Methoxin, Oxoxatexidonoxin, Oxoxinatexidonoxin, Oxoxinatex, Oxoxinatexinoxin, Oxoxinate , Phosalones, Profenofos, Pyraclofos, Pyridaben, Pyrimidifen, Tebufenpyrad, Thuringiensin, Triarathene as well as 4-Bromo-2- (4-chlorophenyl) -l - (ethoxymethyl) -5- (trifluoromethyl) -lH-pyrrole-3-carbonitrile (AC 303630).

When used as insecticides and acaricides, the active compounds according to the invention can also be present in their commercially available formulations and in the use forms prepared from these formulations 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 use forms prepared from the commercially available formulations can vary within wide limits when used as insecticides and acaricides. The active substance concentration of the use forms can be from 0.0000001 to 95% by weight of active substance, preferably between 0.0001 and 1% by weight.

The agents used to protect technical materials generally contain the active ingredients 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 on the composition of the material to be protected. The optimal amount can be determined by test series. In general, the application concentrations are in the range from 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 activity of the active substances which can be used according to the invention or of the agents, concentrates or very general formulations which can be derived therefrom can be increased if further antimicrobial compounds, fungicides, bactericides, herbicides, insecticides or other active substances are used to enlarge the spectrum of activity or to achieve special effects such as additional protection against insects. These mixtures can have a broader spectrum of activity than the compounds according to the invention.

In many cases, synergistic effects are obtained, i.e. the effectiveness of the mixture is greater than the effectiveness of the individual components. Particularly favorable mix partners are e.g. 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 bisthiocyanate (MBT);

quaternary ammonium compounds such as benzyldimethyltetradecylammonium chloride, benzyldimethyldodecylammonium chloride, dodecyldimethylammonium chloride;

Moφhoünderivate such as Cn-Ci4-4-alkyl-2,6-dimethyl-Moφholinhomologe (Tride-moφh), (±) -cis-4- [tert-butylphenyl) -2-methylpropyl] -2,6-dimethylmoφholin (Fen ¬ propimoφh), Faümoφ;

Phenols such as o-phenylphenol, tribromophenol, tetrachloφhenol, pentachloφhenol, 3-methyl-4-chloφhenol, dichlorophene, chlorophene or their salts;

Azoles such as triadimefon, triadimenol, bitertanol, tebuconazole, propiconazole, aza-conazole, hexaconazole, prochloraz, cyproconazole, l- (2-chloro-phenyl) -2- (l -chlor cyclopropyl) -3- (1, 2,4-triazol-1-yl) -propan-2-ol or 1 - (2-chloro-phenyl) -2- (1, 2,4-triazole-1-yl- methyl) -3,3-dimethylbutan-2-ol.

Iodopropargyl 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. Diiodomethyl p-tolyl sulfone;

Bromine derivatives such as bromopol;

Isothiazolines such as N-methyusothiazoun-3-one, 5-chloro-N-methylisothiazoun-3-one, 4,5-dichloro-N-octylisothiazoun-3-one, N-octyusothiazolin-3-one (octilinones);

Benzisothiazolinone, Cyclopentenisothazoüne;

Pyridines such as l-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, 12O, 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) etc. Halogenated microbicides such as Cl-Ac, MCA, tectamer, bromopol, bromidox;

Benzothiazoles such as 2-mercaptobenzothiazoles; so. 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) -tributyltin 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, l- (4-chlθφhenyl) -4- (O-ethyl, S-propyl) phosphoryloxypyrazole (TIA-230), Chloφyrifos, Coumaphos, Demetone, Demeton-S-methyl, Diazinon, Dichlorfos, Dimethoate, Ethoprophos, Etrimfos, Fenitrothion, Fention, Heptenophos, Parathion, Parathion-methyl, Phosalone, Phoxim, Pirimiphos-ethyl, Pirimiphos-methyl, Profenofos, Prothiofos, Sulprofos, Triazophon and Trichloφ.

Carbamates such as aldicarb, bendiocarb, BPMC (2- (l-methylpropyl) phenylmethylcarbamate), butocarboxime, butoxycarboxime, carbaryl, carbofuran, carbosulfan, cloethocarb, isoprocarb, methomyl, oxamyl, pirimicarb, promecarb, propoxur and thiodine.

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-trifluoromethylvinyl) - cyclopφpancarboxylat, 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-1 H-imidazol-2-amine (imidachloprid).

Organosilicon compounds, preferably dimethyl (phenyl) silylmethyl-3-phenoxybenzyl ether such as dimethyl (4-ethoxyphenyl) silylmethyl-3-phenoxybenzyl ether or dimethyl (phenyl) silylmethyl-2-phenoxy-6-pyridylmethyl ether such as dimethyl (9-ethoxyphenyl) silylmethyl-2-phenoxy-6-pyridylmethyl ether or (phenyl) [3 - (3-phenoxyphenyl) propyl] ( dimethyl) silanes such as (4-ethoxyphenyl) - [3 (4-fluoro-3-phenoxyphenyl) propyl] dimethylsilane.

Other active substances which can be used are algicides, muusicides, active substances against "sea animals", which relate, for example, to Place ship floor paints.

The following examples illustrate the preparation of active substances and their use according to the invention.

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Manufacturing examples

example 1

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

The compounds of the formula (I) listed in Table 1 below are prepared analogously to Example 1 and in accordance with the general description of the process according to the invention:

Table 1

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Table 1 (continued)

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Table 1 (continued)

Table 1 (continued)

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50

Table 1 (continued)

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Table 1 (continued)

Examples of use

In the following application examples, the compounds listed below were used as comparison substances:

(A)

CF, - Vco- NH- // w -C ₃ H ₇ -i

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

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

2-Hydroxy-4-trifluoromethyl-N- (3,5-dichloro phhenyl) benzamide

(D)

CF ₃ X // '\\) - _ CO-N „H, - // w

2-hydroxy-4-trifluoromethyl-N- (3-chlθφhenyl) 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 parts by weight of alkyl aryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

To test for protective efficacy, young plants are sprayed with the active ingredient preparation to drip-hate. After the spray coating has dried on, the plants are inoculated with an "aqueous spore suspension of Phytophthora infestans.

The plants are placed in an incubation cabin with 100% relative humidity and approx. 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 at an active ingredient concentration of 10 ppm an efficiency of 70% to 100%, while the comparison substance (C) has an efficiency of 15% . Example B

Plasmopara test (vine) / protectiv

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.

To test for protective efficacy, young plants are sprayed with the active ingredient preparation to drip-hate. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of Plasmopara viticola and then remain in a moist chamber at 20-22 ° C. and 100% relative atmospheric humidity for 1 day. The plants are then placed in a greenhouse at 21 ° C. and 90% humidity for 5 days. The plants are then moistened and placed in a moisture chamber for 1 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 with an 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 parts by weight of alkyl aryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and the concentrate is diluted with water and the stated amount of emulsifier to the desired concentration.

To test for protective efficacy, young rice plants are sprayed with the preparation of active compound until they are dripping. After the spray coating has dried, the plants are inoculated with an aqueous spore suspension of Pyricularia oryzae. The plants are then placed in a greenhouse at 100% relative atmospheric 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 from 0.025 ppm an efficiency of 80% to 100%.

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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, 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted to the desired concentrations with water containing emulsifier.

Cabbage leaves (Brassica oleracea) are treated with the active ingredient preparation of the desired concentration. A treated leaf is placed in the plastic can and filled with larvae (L2) of the cockroach (PluteUa xylosteüa). After 3 days, an untreated sheet is used for refilling.

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

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

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

Bean plants (Phaseolus vulgaris), which are heavily infested with all stages of the common spider mite Tetranychus urticae, are immersed in an active ingredient preparation of the desired concentration.

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

In this test, the compounds of Examples 78, 98 and 103, at an active substance concentration of 0.01%, show a degree of killing of 80% to 100% after 7 days, while the comparison substances (A), (B), (E) and ( F) 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, 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentrations.

Cabbage leaves (Brassica oleracea) are treated by dipping into the active ingredient preparation of the desired concentration and populated with horseradish leaf beetle larvae (Phaedon cochleariae) 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 no beetle larvae have been killed.

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

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Example G

Plutella test

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

Cabbage leaves (Brassica oleracea) are treated by dipping into the active ingredient preparation of the desired concentration and populated with caterpillars of the cockroach (Plutella maculipennis) while 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, at an active substance concentration of 0.1%, show a degree of killing of 85% to 100% after 7 days, while the comparison substance (B) has no effect.

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Example H

Material protection test

Inhibition test on giant colonies of Basidiomycetes

Colonies of Gloeophyüum trabeum, Coniophora puteana, Poria placenta, Lentinus tigrinus, Coriolus versicolor and Stereum sanguinolentum were excised and mycelium pieces were incubated at 26 ° C on an agar medium containing malt extract peptone. The inhibition of hyphal growth on active nutrient media was compared with the lengthy growth on nutrient media without the addition of an active ingredient and rated as a percentage inhibition.

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

Claims

1. 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- (Cj-C3) alkylphenyl; 3,5-dichlorophene; 3-chloro-4-methylphenyl and 3,4-dimethylphenyl.

Compounds of the formula (HI)

in which

Rl, R ^, R ³ and R ^ independently of one another for 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; 5170

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Amino, aminocarbonyl; in each case straight-chain or branched alkylamino, 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 mono- to trisubstituted, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms, at least one of the radicals R *, R ^, R ³ and R ^ not being hydrogen and except the compounds: 3-Chlθφhenyl; 3-bromophenyl; 3-methylphenyl; 3-trifluoromethylphenyl; 4-chlorophenyl; 4-methoxyphenyl; 4-trifluoromethylphenyl; 4- (Cι- C3) alkylphenyl; 3,5-dichlorophene; 3-chloro-4-methylphenyl and 3,4-dimethylphenyl.

3. Compounds of formula (HI) according to claim 2,

in which

R, R-, R ³ and R ^ independently of one another for 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-propylamino, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylamino carbonyl, dimethylamino, ethylmethylamino, methyl-n-propylamino, methyl-i-propylamino, diethylamino, Dimethylaminocarbonyl, ethylmethylaminocarbonyl, 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 R 1, R 4, R ³ and R 4 does not represent hydrogen and with the exception of the compounds: 3-chlorophenyl; 3-bromophenyl; 3-methylphenyl; 3-trifluoromethylphenyl; 4-chlorophenyl; 4-methoxyphenyl; 4-trifluoromethylphenyl; 4- (C \ - C3) alkylphenyl; 3,5-dichlorophene; 3-chloro-4-methylphenyl and 3,4-dimethylphenyl.

4. Compounds of formula (ILT) according to claim 2 in which

Rl, R-, R ³ and R ^ independently of one another for 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,

Butenyloxy, isobutenyloxy, propenylthio, butenylthio or isobutenylthio, where at least one of the radicals R ^, R ^, R ³ and R ^ is not hydrogen and with the exception of the compounds: 3-chloro-phenyl; 3-bromophenyl; 3-methylphenyl; 3-trifluoromethylphenyl; 4-chlθφhenyl; 4-methoxyphenyl; 4-trifluoromethylphenyl; 4- (C _j -

C3) alkylphenyl; 3,5-dichlorophene; 3-chloro-4-methylphenyl and 3,4-dimethylphenyl.

5. pesticide, characterized by a content of at least one compound of the formula (I) according to claim 1. 6. A method for controlling pests, characterized in that compounds of the formula (I) according to Claim 1 are allowed to act on pests and / or their habitat.

7. Use of compounds of the formulas (I) or (IH) according to Claims 1 to 4 for combating pests.

8. A process for the preparation of pesticides, characterized in that compounds of the formulas (I) or (HI) according to Claims 1 to 4 are mixed with extenders and / or surface-active agents.

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), ^ N-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.