DE10215291A1 - Microbicidal agents based on biphenylbenzamide derivatives - Google Patents

Abstract

New microbicidal agents based on biphenylbenzamide derivatives of the general formula (I) DOLLAR F1 in which DOLLAR AR · 1 ·, R · 2 ·, R · 3 · and m have the meanings given in the description, DOLLAR A and new biphenylbenzamides, several processes for the production of these substances and their use for controlling pests, as well as new intermediates and processes for their production.

Description

The present invention relates to novel microbicidal agents based in part known biphenylbenzamide derivatives and the use of these substances Control of unwanted microorganisms. The invention also relates to new ones Biphenylbenzamide derivatives and several processes for their preparation.

It is already known that biphenylbenzamide derivatives for combating types of phytopathogenic fungus Botrytis can be used (cf. EP-A 0 545 099). The However, the effectiveness of these previously known compounds is particularly low Application rates are not completely satisfactory in all areas of application.

Furthermore, certain biphenylbenzamide derivatives are known, such as, for example Compounds N- (2'-fluoro-1,1'-biphenyl-2-yl) -2- (trifluoromethyl) benzamide and N- (4'- Fluoro-1,1'-biphenyl-2-yl) -2- (trifluoromethyl) benzamide (cf. EP-A 0 545 099).

So far, nothing has been said about the broad fungicidal applicability of these compounds known. It is also not known to what extent these connections against others microbial, e.g. B. bacterial, pests can be used.

It has now been found that the partially known biphenylbenzamide derivatives of the formula (I)


in which
R ^{1 represents} methyl, trifluoromethyl, chlorine, bromine or iodine,
R ^{2 represents} hydrogen or fluorine,
R ³ for halogen, cyano, nitro, C ₁ -C ₆ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ - C ₄ alkylsulfonyl, C ₂ -C ₆ alkenyl, C ₃ -C ₆ cycloalkyl, or represents C ₁ -C ₆ haloalkyl, C ₁ -C ₆ haloalkoxy, C ₁ -C ₆ haloalkylthio or C ₁ -C ₆ haloalkylsulfonyl each having 1 to 13 halogen atoms,
m represents 1, 2, 3, 4 or 5, where the radicals R ^{3 can be the} same or different if m represents 2, 3, 4 or 5.
very good for combating phytopathogenic pathogens from the class of the Chytridiomycetes (subdivision of the Mastigomycotina), the class of the Zygomycetes (Zygomycotina), the classes of the Hemiascomycetes, Plectomycetes, Pyrenomycetes, Pyrenomycetes, Laboulbeniomycetes, Locoloascomycabella (Locoloascomycab) from Locoloascomycotab and Deuteromycotina, as well as harmful microorganisms in material protection.

The compounds of formula (I), depending on the type of Substituents as geometric and / or optical isomers or mixtures of isomers different composition. The invention relates to both Use of the pure isomers as well as the isomer mixtures.

The biphenylbenzamide derivatives which can be used according to the invention are characterized by Formula (I) generally defined.

Biphenylbenzamide derivatives of the formula (I) in which
R ^{1 represents} trifluoromethyl, chlorine, bromine or iodine,
R ^{2 represents} hydrogen or fluorine,
R ³ for halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₂ -C ₄ alkenyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or for C ₁ - C ₄ haloalkyl, C ₁ -C ₄ haloalkoxy or C ₁ -C ₄ haloalkylthio each having 1 to 9 halogen atoms,
m stands for 1, 2, 3, where the radicals R ^{3 can be the} same or different if m stands for 2 or 3.

Biphenylbenzamide derivatives of the formula (I), in which
R ^{1 represents} trifluoromethyl or iodine,
R ^{2 represents} hydrogen,
R ³ for fluorine, chlorine, bromine, iodine, methyl, ethyl, n-, i-propyl, n-, i-, s-, t-butyl, methoxy, ethoxy, methylthio, ethylthio, or for C ₁ -C ₂ Haloalkyl, C ₁ -C ₂ haloalkoxy or C ₁ -C ₂ haloalkylthio each having 1 to 5 halogen atoms,
m stands for 1, 2, where the radicals R ^{3 can be the} same or different if m stands for 2.

Biphenylbenzamide derivatives of the formula (I) in which
R ^{1 represents} trifluoromethyl or iodine,
R ^{2 represents} hydrogen,
R ^{3 represents} fluorine, chlorine, bromine, methyl, methoxy, methylthio, trifluoromethyl, trifluoromethoxy or trifluoromethylthio,
m stands for 1, 2, where the radicals R ^{3 can be the} same or different if m stands for 2.

Compounds of the formula (I) in which R ^{1 represents} trifluoromethyl are also very particularly preferably used.

Compounds of the formula (I) in which R ^{1 represents} iodine can also be used with very particular preference.

Compounds of the formula (I) in which R ^{2 represents} hydrogen can also be used with very particular preference.

Compounds of the formula (I) in which R ^{2 represents} fluorine are also very particularly preferably used.

Compounds of the formula (I) in which R ^{3 represents} fluorine, chlorine or bromine can also be used with very particular preference.

Compounds of the formula (I) in which R ^{3 represents} trifluoromethyl, trifluoromethoxy or trifluoromethylthio can also be used with very particular preference.

Compounds of the formula (I) are also very particularly preferably used, in which m stands for 2.

The biphenylbenzamide derivatives of the formula (I) which can be used according to the invention are suitable are very good at combating class phytopathogenic pathogens Chytridiomycetes, Zygomycetes, Hemiascomycetes, Plectomycetes, Pyrenomycetes, Pyrenomycetes, Laboulbeniomycetes, Locoloascomycetes, Basidiomycetes and Deuteromycetes, as well as harmful microorganisms in material protection such as Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.

Some pathogens of fungal and bacterial diseases that fall under the generic names listed above may be mentioned as examples, but not by way of limitation:
Xanthomonas species, such as, for example, Xanthomonas campestris pv. Oryzae;
Pseudomonas species, such as, for example, Pseudomonas syringae pv. Lachrymans;
Erwinia species, such as, for example, Erwinia amylovora;
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 (conidial form: Drechslera, Syn: Helminthosporium);
Cochliobolus species, such as, for example, Cochliobolus sativus (conidial form: Drechslera, 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;
Pellicularia species, such as, for example, Pellicularia sasakii;
Pyricularia species, such as, for example, Pyricularia oryzae;
Fusarium species, such as, for example, Fusarium culmorum;
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.

According to the invention, the following pathogens of fungal and bacterial diseases can preferably be combated by using the compounds of the formula (I):
Pseudomonas species, such as, for example, Pseudomonas syringae pv. Lachrymans;
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 (conidial form: Drechslera, Syn: Helminthosporium);
Cochliobolus species, such as, for example, Cochliobolus sativus (conidial form: Drechslera, 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;
Pellicularia species, such as, for example, Pellicularia sasakii;
Pyricularia species, such as, for example, Pyricularia oryzae;
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.

According to the invention, the following pathogens of fungal and bacterial diseases can be particularly preferably combated by using the compounds of the formula (I):
Sphaerotheca species, such as, for example, Sphaerotheca fuliginea;
Podosphaera species, such as, for example, Podosphaera leucotricha;
Venturia species, such as, for example, Venturia inaequalis;
Uromyces species, such as, for example, Uromyces appendiculatus;
Puccinia species, such as, for example, Puccinia recondita;
Pellicularia species, such as, for example, Pellicularia sasakii;
Cercospora species, such as, for example, Cercospora canescens;
Alternaria species, such as, for example, Alternaria brassicae.

The biphenylbenzamide derivatives of the formula (I) which can be used according to the invention are partially known (cf. EP-A 0 545 099).

The biphenylbenzamide derivatives of the formula (Ia) (group 1) are new


in which
R ^{1 represents} methyl, trifluoromethyl, chlorine, bromine or iodine,
R ^{2 represents} hydrogen or fluorine,
R ³ for halogen, cyano, nitro, C ₁ -C ₆ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ - C ₄ alkylsulfonyl, C ₂ -C ₆ alkenyl, C ₃ -C ₆ cycloalkyl, or for C ₁ -C ₆ haloalkyl, C ₁ -C ₆ haloalkoxy, C ₁ -C ₆ haloalkylthio or C ₁ -C ₆ haloalkylsulfonyl each having 1 to 13 halogen atoms,
n represents 2, 3, 4 or 5, where the radicals R ^{3 may be the} same or different.

Preferred are biphenylbenzamide derivatives of the formula (Ia) in which
R ^{1 represents} trifluoromethyl, chlorine, bromine or iodine,
R ^{2 represents} hydrogen or fluorine,
R ³ for halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₂ -C ₄ alkenyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or for C ₁ - C ₄ haloalkyl, C ₁ -C ₄ haloalkoxy or C ₁ -C ₄ haloalkylthio each having 1 to 9 halogen atoms,
n represents 2, 3, where the radicals R ^{3 may be the} same or different.

Biphenylbenzamide derivatives of the formula (Ia) in which are particularly preferred
R ^{1 represents} trifluoromethyl or iodine,
R ^{2 represents} hydrogen,
R ³ for fluorine, chlorine, bromine, iodine, methyl, ethyl, n-, i-propyl, n-, i-, s-, t-butyl, methoxy, ethoxy, methylthio, ethylthio, or for C ₁ -C ₂ Haloalkyl, C ₁ -C ₂ haloalkoxy or C ₁ -C ₂ haloalkylthio each having 1 to 5 halogen atoms,
n stands for 2, where the radicals R ^{3 can be the} same or different.

Biphenylbenzamide derivatives of the formula (Ia) in which
R ^{1 represents} trifluoromethyl or iodine,
R ^{2 represents} hydrogen,
R ^{3 represents} fluorine, chlorine, bromine, methyl, methoxy, methylthio, trifluoromethyl, trifluoromethoxy or trifluoromethylthio,
n stands for 2, where the radicals R ^{3 can be the} same or different.

Also new are biphenylbenzamide derivatives of the formula (Ib) (Group 2)


in which
R ^{1 represents} methyl, trifluoromethyl, chlorine, bromine or iodine,
R ^{20 represents} fluorine,
R ³ for halogen, cyano, nitro, C ₁ -C ₆ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ - C ₄ alkylsulfonyl, C ₂ -C ₆ alkenyl, C ₃ -C ₆ cycloalkyl, or represents C ₁ -C ₆ haloalkyl, C ₁ -C ₆ haloalkoxy, C ₁ -C ₆ haloalkylthio or C ₁ -C ₆ haloalkylsulfonyl each having 1 to 13 halogen atoms,
m represents 1, 2, 3, 4 or 5, where the radicals R ^{3 can be the} same or different if m represents 2, 3, 4 or 5.

Preferred are biphenylbenzamide derivatives of the formula (Ib) in which
R ^{1 represents} trifluoromethyl, chlorine, bromine or iodine,
R ^{20 represents} fluorine,
R ³ for halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₂ -C ₄ alkenyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or for C ₁ - C ₄ haloalkyl, C ₁ -C ₄ haloalkoxy or C ₁ -C ₄ haloalkylthio each having 1 to 9 halogen atoms,
m stands for 1, 2, 3, where the radicals R ^{3 can be the} same or different if m stands for 2 or 3.

Biphenylbenzamide derivatives of the formula (Ib), in which
R ^{1 represents} trifluoromethyl or iodine,
R ^{20 represents} fluorine,
R ³ for fluorine, chlorine, bromine, iodine, methyl, ethyl, n-, i-propyl, n-, i-, s-, t-butyl, methoxy, ethoxy, methylthio, ethylthio, or for C ₁ -C ₂ Haloalkyl, C ₁ -C ₂ haloalkoxy or C ₁ -C ₂ haloalkylthio each having 1 to 5 halogen atoms,
m stands for 1, 2, where the radicals R ^{3 can be the} same or different if m stands for 2.

Biphenylbenzamide derivatives of the formula (Ib), in which
R ^{1 represents} trifluoromethyl or iodine,
R ^{20 represents} fluorine,
R ^{3 represents} fluorine, chlorine, bromine, methyl, methoxy, methylthio, trifluoromethyl, trifluoromethoxy or trifluoromethylthio,
m stands for 1, 2, where the radicals R ^{3 can be the} same or different if m stands for 2.

Also new are biphenylbenzamide derivatives of the formulas (Ic) (Group 3), (Id) (Group 4) and (Ie) (Group 5)


in which each
R ^{1 represents} methyl, trifluoromethyl, chlorine, bromine or iodine,
R ^{2 represents} hydrogen or fluorine,
R ³¹ , R ³² and R ³³ independently of one another for halogen, cyano, nitro, C ₁ -C ₆ alkyl, C ₁ - C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylsulfonyl, C ₂ -C ₆ alkenyl, C ₃ -C ₆ cycloalkyl, or C ₁ -C ₆ haloalkyl, C ₁ -C ₆ haloalkoxy, C ₁ -C ₆ haloalkylthio or C ₁ -C ₆ haloalkylsulfonyl, each with 1 to 13 halogen atoms,
with the proviso that R ³¹ and R ^{33 are} each not fluorine if R ^{1 is} trifluoromethyl and R ^{2 is} hydrogen.

Preferred are biphenylbenzamide derivatives of the formulas (Ic), (Id) and (Ie), in each of which
R ^{1 represents} trifluoromethyl, chlorine, bromine or iodine,
R ^{2 represents} hydrogen or fluorine,
R ³¹ , R ³² and R ³³ independently of one another for halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ - C ₄ alkylthio, C ₂ -C ₄ alkenyl, cyclopropyl, cyclobutyl, cyclopentyl , Cyclohexyl, or C ₁ -C ₄ haloalkyl, C ₁ -C ₄ haloalkoxy or C ₁ -C ₄ haloalkylthio each having 1 to 9 halogen atoms,
with the proviso that R ³¹ and R ^{33 are} each not fluorine if R ^{1 is} trifluoromethyl and R ^{2 is} hydrogen.

Biphenylbenzamide derivatives of the formulas (Ic), (Id) and (Ie), in each of which are particularly preferred
R ^{1 represents} trifluoromethyl or iodine,
R ^{2 represents} hydrogen,
R ³¹ , R ³² and R ³³ independently of one another for fluorine, chlorine, bromine, iodine, methyl, ethyl, n-, i-propyl, n-, i-, s-, t-butyl, methoxy, ethoxy, methylthio, ethylthio , or represent C ₁ -C ₂ haloalkyl, C ₁ -C ₂ haloalkoxy or C ₁ -C ₂ haloalkylthio each having 1 to 5 halogen atoms,
with the proviso that R ³¹ and R ^{33 are} each not fluorine if R ^{1 is} trifluoromethyl and R ^{2 is} hydrogen.

Biphenylbenzamide derivatives of the formulas (Ic), (Id) and (Ie), in each of which are very particularly preferred
R ^{1 represents} trifluoromethyl or iodine,
R ^{2 represents} hydrogen,
R ³¹ , R ³² and R ³³ independently of one another represent fluorine, chlorine, bromine, methyl, methoxy, methylthio, trifluoromethyl, trifluoromethoxy or trifluoromethylthio,
with the proviso that R ³¹ and R ^{33 are} each not fluorine if R ^{1 is} trifluoromethyl and R ^{2 is} hydrogen.

It was also found that the new biphenylbenzamide derivatives of the formulas (Ia), (Ib), (Ic), (Id) and (Ie) have very good microbicidal properties and for Combating unwanted microorganisms both in crop protection and in Material protection can be used.

The general or preferred areas listed above Residual definitions or explanations can also be among themselves, that is, between the respective areas and preferred areas can be combined as desired. They apply to the End products as well as for the preliminary and intermediate products accordingly. Moreover individual definitions can also be omitted.

Saturated hydrocarbon residues such as alkyl can, also in combination with Heteroatoms such as B. in alkoxy, as far as possible, in each case straight-chain or be branched.

Halogen-substituted radicals, e.g. B. haloalkyl, are single or multiple halogenated up to the maximum possible number of substituents. With multiple Halogenation, the halogen atoms can be the same or different. Halogen is included for fluorine, chlorine, bromine or iodine, in particular for fluorine, chlorine or bromine.

• A) Benzoylhalogenide der Formel (II)
  
  
  in welcher
  R¹ die oben angegebenen Bedeutungen hat,
  X¹ für Halogen steht,
  mit Anilinderivaten der Formel (III)
  
  
  in welcher
  R², R³ und m die oben angegebenen Bedeutungen haben,
  gegebenenfalls in Gegenwart eines Säurebindemittels und gegebenenfalls in Gegenwart eines Verdünnungsmittels umsetzt, oder
• B) Halogenbenzamide der Formel (IV)
  
  
  in welcher
  R¹ und R² die oben angegebenen Bedeutungen haben,
  X² für Brom oder Iod steht,
  mit Boronsäurederivaten der Formel (V)
  
  
  in welcher
  R³ und m die oben angegebenen Bedeutungen haben,
  G¹ und G² jeweils für Wasserstoff oder zusammen für Tetramethylethylen stehen,
  in Gegenwart eines Katalysators, gegebenenfalls in Gegenwart eines Säurebindemittels und gegebenenfalls in Gegenwart eines Verdünnungsmittels umsetzt, oder
• C) Benzamid-Boronsäure-Derivate der Formel (VI)
  
  
  in welcher
  R¹ und R² die oben angegebenen Bedeutungen haben,
  G³ und G⁴ jeweils für Wasserstoff oder zusammen für Tetramethylethylen stehen,
  mit Halogenbenzolderivaten der Formel (VII)
  
  
  in welcher
  R³ und m die oben angegebenen Bedeutungen haben und
  X³ für Brom, Iod oder Trifluormethylsulfonyloxy steht,
  in Gegenwart eines Katalysators, gegebenenfalls in Gegenwart eines Säurebindemittels und gegebenenfalls in Gegenwart eines Verdünnungsmittels umsetzt, oder
• D) Halogenbenzamide der Formel (IV)
  
  
  in welcher
  R¹ und R² die oben angegebenen Bedeutungen haben,
  X² für Brom oder Iod steht,
  in einer ersten Stufe mit einem Diboran-Derivat der Formel (VIII)
  
  
  in welcher
  G⁵ und G⁶ jeweils für Alkyl oder gemeinsam für Alkandiyl stehen,
  in Gegenwart eines Katalysators, gegebenenfalls in Gegenwart eines Säurebindemittels und gegebenenfalls in Gegenwart eines Verdünnungsmittels umsetzt und ohne Aufarbeitung in einer zweiten Stufe mit Halogenbenzolderivaten der Formel (VII)
  
  
  in welcher
  R³ und m die oben angegebenen Bedeutungen haben und
  X³ für Brom, Iod oder Trifluormethylsulfonyloxy steht,
  in Gegenwart eines Katalysators, gegebenenfalls in Gegenwart eines Säurebindemittels und gegebenenfalls in Gegenwart eines Verdünnungsmittels umsetzt.

Biphenylbenzamide derivatives of the formulas (Ia), (Ib), (Ic), (Id) and (Ie) are each subgroups of the compounds of the formula (I) which can be used according to the invention. These connections can be made in basically the same way. The preparation of the compounds of the formula (I) is therefore described below by way of example. Compounds of formula (I) can be prepared by

• A) Benzoyl halides of the formula (II)
  
  
  in which
  R ^{1 has} the meanings given above,
  X ^{1 represents} halogen,
  with aniline derivatives of the formula (III)
  
  
  in which
  R ² , R ³ and m have the meanings given above,
  if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent, or
• B) halobenzamides of the formula (IV)
  
  
  in which
  R ¹ and R ^{2 have} the meanings given above,
  X ^{2 represents} bromine or iodine,
  with boronic acid derivatives of the formula (V)
  
  
  in which
  R ³ and m have the meanings given above,
  G ¹ and G ² each represent hydrogen or together represent tetramethylethylene,
  in the presence of a catalyst, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent, or
• C) Benzamide-boronic acid derivatives of the formula (VI)
  
  
  in which
  R ¹ and R ^{2 have} the meanings given above,
  G ³ and G ⁴ each represent hydrogen or together represent tetramethylethylene,
  with halogenobenzene derivatives of the formula (VII)
  
  
  in which
  R ³ and m have the meanings given above and
  X ^{3 represents} bromine, iodine or trifluoromethylsulfonyloxy,
  in the presence of a catalyst, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent, or
• D) halobenzamides of the formula (IV)
  
  
  in which
  R ¹ and R ^{2 have} the meanings given above,
  X ^{2 represents} bromine or iodine,
  in a first stage with a diborane derivative of the formula (VIII)
  
  
  in which
  G ⁵ and G ⁶ each represent alkyl or together represent alkanediyl,
  in the presence of a catalyst, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent and without working up in a second stage with halogenobenzene derivatives of the formula (VII)
  
  
  in which
  R ³ and m have the meanings given above and
  X ^{3 represents} bromine, iodine or trifluoromethylsulfonyloxy,
  in the presence of a catalyst, optionally in the presence of an acid binder and optionally in the presence of a diluent.

If, for example, 2- (trifluoromethyl) benzoyl chloride and 4'-chloro-1,1'-biphenyl-2-amine are used as starting materials and a base, the course of process A) according to the invention can be illustrated by the following reaction equation:

Formula (II) provides a general definition of the benzoyl halides required as starting materials for carrying out process A) according to the invention. In this formula (II), R ^{1 is} preferably, particularly preferably or very particularly preferably those meanings which have already been indicated as preferred, particularly preferred, etc. for this radical in connection with the description of the compounds of the formula (I) which can be used according to the invention , X ¹ preferably represents chlorine.

The benzoyl halides of the formula (II) are known and / or can be reduced produce known processes (compare, for example, EP-A 0 276 177).

Formula (III) provides a general definition of the aniline derivatives required as starting materials for carrying out process A) according to the invention. In this formula (III), R ² , R ³ and m are preferably, particularly preferably or very particularly preferably those meanings which, in connection with the description of the compounds of the formula (I) which can be used according to the invention, are preferred, particularly preferred, etc. were specified for these residues.

The aniline derivatives of the formula (III) are known and / or can be prepared according to known ones Produce methods (see e.g. Bull. Korean Chem. Soc. 2000, 21, 165-166; Chem. Pharm. Bull. 1992, 40, 240-4; JP 9132567).

If, for example, N- (2-iodophenyl) -2- (trifluoromethyl) benzamide and 4-chlorophenylboronic acid are used as starting materials, and a catalyst and a base, the course of process b) according to the invention can be illustrated by the following reaction equation:

Formula (IV) provides a general definition of the halobenzamides required as starting materials for carrying out process B) according to the invention. In this formula (IV), R ¹ and R ^{2 are} preferably, particularly preferably or very particularly preferably those meanings which, in connection with the description of the compounds of the formula (I) which can be used according to the invention, are preferred, particularly preferred, etc. for these Remains were specified. X ² preferably represents bromine or iodine.

• A) Benzoylhalogenide der Formel (II)
  
  
  in welcher
  R¹ die oben angegebenen Bedeutungen hat,
  X¹ für Halogen steht,
  mit 2-Bromanilin oder 2-Iodanilin umsetzt.

The halobenzamides of the formula (IV) are not yet known. They are new chemical compounds and are also the subject of the present application. You will get by one

• A) Benzoyl halides of the formula (II)
  
  
  in which
  R ^{1 has} the meanings given above,
  X ^{1 represents} halogen,
  with 2-bromoaniline or 2-iodoaniline.

The starting materials for carrying out process E) according to the invention required benzoyl halides of formula (II) are already in the above Connection with the method A) according to the invention has been described.

The continue to carry out the method E) as Starting materials required 2-bromoaniline or 2-iodoaniline are known Chemicals for synthesis.

Formula (V) provides a general definition of the boronic acid derivatives required as starting materials for carrying out process B) according to the invention. In this formula (V), R ³ and m are preferably, particularly preferably or very particularly preferably those meanings which, in connection with the description of the compounds of the formula (I) which can be used according to the invention, are preferred, particularly preferred, etc. for these radicals were specified. G ¹ and G ² are preferably each hydrogen or together tetramethylethylene.

Boronic acid derivatives of the formula (V) are known synthetic chemicals. You can also immediately before the reaction directly from halobenzene derivatives and Boronic acid esters are produced and further implemented without working up.

If, for example, N [2- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl] -2- (trifluoromethyl) benzamide and 4-chlorophenyl-trifluoromethanesulfonic acid are used as starting materials, as well as Catalyst and a base, the course of process C) according to the invention can be illustrated by the following reaction equation:

Formula (VI) provides a general definition of the benzamide-boronic acid derivatives required as starting materials for carrying out process C) according to the invention. In this formula (VI), R ¹ and R ^{2 are} preferably, particularly preferably or very particularly preferably those meanings which, in connection with the description of the compounds of the formula (I) which can be used according to the invention, are preferred, particularly preferred, etc. for these Remains were specified. G ³ and G ⁴ are preferably each hydrogen or together tetramethylethylene.

The benzamide-boronic acid derivatives of the formula (VI) are not yet known. she are new chemical compounds and also the subject of the present Registration.

• A) Benzoylhalogenide der Formel (II)
  
  
  in welcher
  R¹ die oben angegebenen Bedeutungen hat,
  X¹ für Halogen steht,
  mit Anilinboronsäurederivaten der Formel (IX)
  
  
  in welcher
  G³ und G⁴ die oben angegebenen Bedeutungen haben,
  gegebenenfalls in Gegenwart eines Säurebindemittels und gegebenenfalls in Gegenwart eines Verdünnungsmittels umsetzt.

You will get by one

• A) Benzoyl halides of the formula (II)
  
  
  in which
  R ^{1 has} the meanings given above,
  X ^{1 represents} halogen,
  with aniline boronic acid derivatives of the formula (IX)
  
  
  in which
  G ³ and G ^{4 have} the meanings given above,
  if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent.

Those used to carry out process F) according to the invention as starting materials required benzoyl halides of formula (II) are already in the above Connection with the method a) according to the invention has been described.

Formula (IX) provides a general definition of the aniline boronic acid derivatives required as starting materials for carrying out process F) according to the invention. In this formula (IX), G ³ and G ⁴ each preferably represent hydrogen or together tetramethylethylene.

Those used to carry out process F) according to the invention as starting materials required aniline boronic acid derivatives of the formula (IX) are known Chemicals for synthesis.

Formula (VII) provides a general definition of the halogenobenzene derivatives required as starting materials for carrying out process C) according to the invention. In this formula (VII), R ³ and m are preferably, particularly preferably or very particularly preferably those meanings which, in connection with the description of the compounds of the formula (I) which can be used according to the invention, are preferred, particularly preferred, etc. for these radicals were specified. X ³ preferably represents bromine, iodine or trifluoromethylsulfonyloxy.

If, for example, N- (2-bromophenyl) -2- (trifluoromethyl) benzamide and 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bi-1 are used, 3,2-dioxaborolane in the first stage and further 4-bromo-1-chloro-2-methylbenzene in the second stage as starting materials, as well as a catalyst and a base in each stage, the course of process D) according to the invention can be as follows Reaction equation can be illustrated:

Those used to carry out process D) according to the invention as starting materials required halobenzamides of the formula (IV) are already above in the Connection with the inventive method B) has been described.

Formula (VIII) provides a general definition of the diborane derivatives also required as starting materials for carrying out process D) according to the invention. In this formula (VIII) G ⁵ and G ⁶ each preferably represent methyl, ethyl, propyl, butyl or together tetramethylethylene.

The diborane derivatives of the formula (VIII) are generally known Chemicals for synthesis.

The to carry out the method D) according to the invention as Halogenbenzene derivatives of the formula (VII) required as starting materials are already further described above in connection with the method C) according to the invention Service.

As a diluent for carrying out process A), E) according to the invention and F) all inert organic solvents are suitable. This includes preferably aliphatic, alicyclic or aromatic hydrocarbons, such as for example petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, Toluene, xylene or decalin; halogenated hydrocarbons, such as Chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, Dichloroethane or trichloroethane; Ethers, such as diethyl ether, diisopropyl ether, methyl t- butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2- Diethoxyethane or anisole or amides, such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or Hexamethylphosphoramide.

Processes A), E) and F) according to the invention are optionally described in In the presence of a suitable acid acceptor. As such, all the usual ones come inorganic or organic bases. These preferably include Alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or bicarbonates, such as sodium hydride, sodium amide, Sodium methylate, sodium ethylate, potassium tert-butoxide, sodium hydroxide, Potassium hydroxide, ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, Ammonium acetate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate, Sodium bicarbonate or cesium carbonate, as well as tertiary amines, such as Trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, N, N-dimethylbenzylamine, Pyridine, N-methylpiperidine, N-methylmorpholine, N, N-dimethylaminopyridine, Diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicycloundecene (DBU).

The reaction temperatures can be carried out when the inventive Processes A), E) and F) can be varied over a wide range. In general one works at temperatures from 0 ° C to 150 ° C, preferably at temperatures from 20 ° C to 110 ° C.

To carry out process A) according to the invention for producing the Compounds of the formula (I) are used per mole of the benzoyl halide of the formula (II) generally 0.2 to 5 moles, preferably 0.5 to 2 moles of aniline derivative Formula (III). The processing takes place according to usual methods.

To carry out process E) according to the invention for producing the Compounds of the formula (III) are used per mole of the benzoyl halide of the formula (II) generally 0.2 to 5 mol, preferably 0.5 to 2 mol, of 2-bromoaniline or 2- Iodaniline. The processing takes place according to usual methods.

To carry out process F) according to the invention for producing the Compounds of the formula (VI) are used per mole of the benzoyl halide of the formula (II) generally 0.2 to 5 mol, preferably 0.5 to 2 mol Aniline boronic acid derivative of the formula (IX). The processing takes place according to usual methods.

As a diluent for carrying out processes B), C) according to the invention and D) all inert organic solvents are suitable. This includes preferably aliphatic, alicyclic or aromatic hydrocarbons, such as for example petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, Toluene, xylene or decalin; Ethers, such as diethyl ether, diisopropyl ether, methyl t- butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2- Diethoxyethane or anisole; Nitriles, such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile; Amides, such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; Esters such as methyl acetate or ethyl acetate; Sulfoxides, such as dimethyl sulfoxide; Sulfones such as sulfolane; Alcohols, such as methanol, ethanol, n- or i-propanol, n-, i-, sec- or tert-butanol, ethanediol, propane-1,2-diol, ethoxyethanol, Methoxyethanol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, their mixtures with water or pure water.

The reaction temperatures can be carried out when the inventive Process B), C) and D) can be varied over a wide range. In general one works at temperatures from 0 ° C to 150 ° C, preferably at temperatures from 20 ° C to 110 ° C.

Processes B), C) and D) according to the invention are optionally in In the presence of a suitable acid acceptor. As such, all the usual ones come inorganic or organic bases. These preferably include Alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, fluorides, phosphates, carbonates or bicarbonates, such as Sodium hydride, sodium amide, lithium diisopropylamide, sodium methylate, sodium ethylate, Potassium tert-butoxide, sodium hydroxide, potassium hydroxide, sodium acetate, Sodium phosphate, potassium phosphate, potassium fluoride, cesium fluoride, sodium carbonate, Potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate or Cesium carbonate and tertiary amines, such as trimethylamine, triethylamine, tributylamine, N, N- Dimethylaniline, N, N-dimethylbenzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), Diazabicyclonones (DBN) or Diazabicycloundecen (DBU).

The processes B), C) and D) according to the invention are carried out in the presence of a Catalyst, such as a palladium salt or complex. Palladium chloride, palladium acetate, Tetrakis (triphenylphosphine) palladium, bis (triphenylphosphine) palladium dichloride or (1,1'-bis- (diphenylphosphino) ferrocene palladium (II) chloride).

A palladium complex can also be generated in the reaction mixture, if you have a palladium salt and a complex ligand, such as. B. triethylphosphine, Tri-tert-butylphosphine, tricyclohexylphosphine, 2- (dicyclohexylphosphine) biphenyl, 2- (di-tert-butylphosphine) biphenyl, 2- (dicyclohexylphosphine) -2 '- (N, N-dimethylamino) biphenyl, triphenylphosphine, tris- (o-tolyl) phosphane, Sodium 3- (diphenylphosphino) benzenesulfonate, tris-2- (methoxyphenyl) phosphine, 2,2'-bis- (diphenylphosphane) -1,1'-binaphthyl, 1,4-bis (diphenylphosphane) butane, 1,2-bis (diphenylphosphane) ethane, 1,4-bis (dicyclohexylphosphane) butane, 1,2-bis (dicyclohexylphosphane) ethane, 2- (dicyclohexylphosphane) -2 '- (N, N-dimethylamino) biphenyl, Bis (diphenylphosphino) ferrocene or tris (2,4-tert-butylphenyl) phosphite separated admits for reaction.

To carry out process B) according to the invention for producing the Compounds of the formula (I) are used per mole of the halobenzamide of the formula (IV) generally 1 to 15 mol, preferably 2 to 8 mol of the boronic acid derivative Formula (V). The processing takes place according to usual methods.

To carry out process C) according to the invention for producing the Compounds of formula (I) are used per mole of the benzamide-boronic acid derivative Formula (VI) generally 1 to 15 moles, preferably 2 to 8 moles Halogenobenzene derivative of the formula (VII). The processing takes place according to usual Methods.

To carry out process D) according to the invention for producing the Compounds of the formula (I) are used per mole of the halobenzamide of the formula (IV) generally 1 to 15 moles, preferably 1 to 5 moles of diborane derivative Formula (VIII) and 1 to 15 moles, preferably 1 to 5 moles, of halogenobenzene derivative of formula (VII).

The processes A), B), C), D), E) and F) are in general carried out under normal pressure. However, it is also possible to increase or reduced pressure - generally between 0.1 bar and 10 bar - to work.

The active compounds of the formulas (Ia), (Ib), (Ic), (Id) and (Ie) according to the invention have a strong microbicidal effect and can be used to combat unwanted microorganisms, such as fungi and bacteria, in crop protection and be used in material protection.

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

Bactericides can be used in plant protection to combat Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae deploy.

Some pathogens of fungal and bacterial diseases that fall under the generic names listed above may be mentioned as examples, but not by way of limitation:
Xanthomonas species, such as, for example, Xanthomonas campestris pv. Oryzae;
Pseudomonas species, such as, for example, Pseudomonas syringae pv. Lachrymans;
Erwinia species, such as, for example, Erwinia amylovora;
Pythium species, such as, for example, Pythium ultimum;
Phytophthora species, such as, for example, Phytophthora infestans;
Pseudoperonospora species, such as, for example, Pseudoperonospora humuli or Pseudoperonospora cubensis;
Plasmopara species, such as, for example, Plasmopara viticola;
Bremia species, such as, for example, Bremia lactucae;
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 (conidial form: Drechslera, Syn: Helminthosporium);
Cochliobolus species, such as, for example, Cochliobolus sativus (conidial form: Drechslera, Syn: Helminthosporium);
Uromyces species, such as, for example, Uromyces appendiculatus;
Puccinia species, such as, for example, Puccinia recondita;
Sclerotinia species, such as, for example, Sclerotinia sclerotiorum;
Tilletia species, such as, for example, Tilletia caries;
Ustilago species, such as, for example, Ustilago nuda or Ustilago avenae;
Pellicularia 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;
Uncinula species, such as, for example, Uncinula necator;
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 active compounds of the formulas (Ia), (Ib), (Ic), (Id) and (Ie) according to the invention have also a strong strengthening effect in plants. They are therefore suitable for Mobilization of the plant's own defenses against attack by unwanted Microorganisms.

Among plant-strengthening (resistance-inducing) substances are in the present Connection to understand such substances that are able to protect the immune system of plants to stimulate the treated plants in subsequent Inoculation with unwanted microorganisms largely resistant to them Develop microorganisms.

In the present case, undesirable microorganisms include phytopathogenic Understand fungi, bacteria and viruses. The substances according to the invention can therefore be used to plant after a certain period of time Protect treatment against infestation by the named pathogens. The period, within which protection is provided generally ranges from 1 to 10 Days, preferably 1 to 7 days after the treatment of the plants with the Agents.

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, of seedlings, and of the soil.

The active compounds of the formulas (Ia), (Ib), (Ic), (Id) and (Ie) according to the invention are suitable also to increase crop yield. They are also less toxic and have good plant tolerance.

The active compounds of the formulas (Ia), (Ib), (Ic), (Id) and (Ie) according to the invention can optionally also in certain concentrations and application rates as Herbicides, for influencing plant growth, as well as for controlling animal pests can be used. If necessary, they can also be used as Use intermediates and precursors for the synthesis of other active ingredients.

According to the invention, all plants and parts of plants can be treated. Under Plants are understood here as all plants and plant populations desired and undesirable wild plants or crops (including naturally occurring crops). Crop plants can be plants that are caused by conventional breeding and optimization methods or by biotechnological and obtained genetic engineering methods or combinations of these methods can be, including the transgenic plants and including by Plant variety rights of protectable or non-protectable plant varieties. Under Plant parts should include all above-ground and underground parts and organs of plants, how sprout, leaf, flower and root are understood, examples being leaves, Needles, stems, stems, flowers, fruiting bodies, fruits and seeds as well as roots, Bulbs and rhizomes are listed. The plant parts also include Crops and vegetative and generative propagation material, for example Cuttings, bulbs, rhizomes, offshoots and seeds.

The treatment of the plants and plant parts according to the invention with the Active substances of the formulas (Ia), (Ib), (Ic), (Id) and (Ie) take place directly or by action on their environment, living space or storage space according to the usual Treatment methods, e.g. B. by dipping, spraying, evaporating, atomizing, scattering, Spread and continue with propagation material, especially seeds single or multi-layer wrapping.

The materials of the formulas (Ia), (Ib), (Ic), (Id) and (Ie) for the protection of technical materials against infestation and Use destruction by unwanted microorganisms.

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 produced 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 may be those of Microorganisms can be attacked or decomposed. As part of the to be protected Materials are also parts of production systems, for example cooling water circuits, called, which can be impaired by the multiplication of microorganisms. in the Within the scope of the present invention, technical materials are preferred Adhesives, glues, papers and cartons, leather, wood, paints, Cooling lubricants and heat transfer liquids called, particularly preferably wood.

As microorganisms that break down or change the technical Materials such as bacteria, fungi, yeast, 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.

Microorganisms of the following genera may be mentioned, for example:
Alternaria, such as Alternaria tenuis,
Aspergillus, such as Aspergillus niger,
Chaetomium, like Chaetomium globosum,
Coniophora, such as Coniophora puetana,
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, like Trichoderma viride,
Escherichia, such as Escherichia coli,
Pseudomonas, such as Pseudomonas aeruginosa,
Staphylococcus, such as Staphylococcus aureus.

The active ingredients can depend on their respective physical and / or chemical properties can be converted into the usual formulations, such as Solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, Fine encapsulation in polymeric substances and in coating compositions for seeds, as well ULV cold and warm fog formulations.

These formulations are prepared in a known manner, e.g. B. by mixing of the active substances with extenders, i.e. liquid solvents, under pressure liquefied gases and / or solid carriers, optionally using of surface-active agents, i.e. emulsifiers and / or dispersants and / or foam-generating agents. In case of using water as Extenders can e.g. B. also used organic solvents as auxiliary solvents become. The following are essentially suitable as liquid solvents: aromatics such as Xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic Hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. B. petroleum fractions, Alcohols, such as butanol or glycol, and their ethers and esters, ketones, such as acetone, Methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulfoxide, and water. With liquefied Gaseous extenders or carriers are those liquids which are used normal temperature and under normal pressure are gaseous, e.g. B. aerosol propellants, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide.

Possible solid carriers are: B. natural stone powder, such as kaolins, Clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic stone powder, such as highly disperse silica, aluminum oxide and Silicates. Possible solid carriers for granules are: 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 organic material such as sawdust, coconut shells, corn cobs and Tobacco stalks. Possible emulsifiers and / or foam-generating agents are: 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. Possible dispersants are: B. Lignin sulfite liquor and methyl cellulose.

In the formulations, adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers are used, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural Phospholipids 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, 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.

The formulations generally contain between 0.1 and 95 percent by weight Active ingredient, preferably between 0.5 and 90%.

The active compounds according to the invention can be used as such or in their formulations also in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides can be used, e.g. B. to broaden the spectrum of activity or prevent development of resistance. In many cases you get it synergistic effects, d. H. the effectiveness of the mixture is greater than the effectiveness of the individual components.

The following compounds, for example, are possible as mixing partners: fungicides aldimorph, ampropylfos, ampropylfos potassium, andoprim, anilazine, azaconazole, azoxystrobin,
Benalaxyl, benodanil, benomyl, benzamacril, benzamacrylic isobutyl, bialaphos, binapacrylic, biphenyl, bitertanol, blasticidin-S, bromuconazole, bupirimate, buthiobate,
Calcium polysulfide, carpropamide, capsimycin, captafol, captan, carbendazim, carboxin, carvone, quinomethionate (quinomethionate), chlobenthiazone, chlorfenazole, chloroneb, chloropicrin, chlorothalonil, chlozolinate, clozylacon, cufraneb, cymroconililanil
Debacarb, dichlorophene, diclobutrazole, diclofluanid, diclomezin, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole, diniconazol-M, dinocap, diphenylamine, dipyrithione, ditalimfos, dithorphoxin, dithorphononodine,
Ediphenphos, Epoxiconazole, Etaconazole, Ethirimol, Etridiazole,
Famoxadone, fenapanil, fenarimol, fenbuconazole, fenfuram, fenhexamid, fenitropan, fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, ferbam, ferimzon, fluazinam, flumetover, fluoromid, fluquinconazol, flurprimidololol, flurprimidolanilus, flurprimidololol, flurprimidololol, flurprimidololol, flurprimidololol, flurprimidololol, flurprimidololol, flurprimidololol, flurprimidololol, flurprimidololol, flurprimidololol, flurprimidololol, flurprimidolutolol Aluminum, fosetyl sodium, fthalide, fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole, furconazole-cis, furmecyclox,
Guazatin, hexachlorobenzene, hexaconazole, hymexazole,
Imazalil, Imibenconazol, Iminoctadin, Iminoctadinealbesilat, Iminoctadinetriacetat, Iodocarb, Ipconazol, Iprobefos (IBP), Iprodione, Iprovalicarb, Irumamycin, Isoprothiolan, Isovaledione,
Kasugamycin, Kresoxim-methyl, copper preparations, such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, oxine-copper and Bordeaux mixture,
Mancopper, Mancozeb, Maneb, Meferimzone, Mepanipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Metrifuroxam, Metiram, Metomeclam, Metsulfovax, Mildiomycin, Myclobutanil, Myclozolin,
Nickel dimethyldithiocarbamate, nitrothal isopropyl, Nuarimol,
Ofurace, Oxadixyl, Oxamocarb, Oxolinicacid, Oxycarboxim, Oxyfenthiin,
Paclobutrazol, pefurazoate, penconazole, pencycuron, phosdiphen, picoxystrobin, PIMARICIN, piperalin, polyoxin, Polyoxorim, probenazole, prochloraz, procymidone, propamocarb, Propanosine sodium, propiconazole, propineb, pyraclostrobin, Pyrazohos, pyrifenox, pyrimethanil, pyroquilon, Pyroxyfur,
Quinconazole, quintozen (PCNB), quinoxyfen
Sulfur and sulfur preparations, spiroxamines
Tebuconazole, tecloftalam, tecnazene, Tetcyclacis, tetraconazole, thiabendazole, Thicyofen, Thifluzamide, thiophanate-methyl, thiram, Tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, Triazbutil, triazoxide, Trichlamid, tricyclazole, tridemorph, trifloxystrobin, triflumizole, triforine, triticonazole,
Uniconazole, validamycin A, vinclozolin, viniconazole,
Zarilamid, Zineb, Ziram as well
Dagger G, OK-8705, OK-8801,
α- (1,1-dimethylethyl) -β- (2-phenoxyethyl) -1H-1,2,4-triazole-1-ethanol,
α- (2,4-dichlorophenyl) -β-fluoro-β-propyl-1H-1,2,4-triazole-1-ethanol,
α- (2,4-dichlorophenyl) -β-methoxy-α-methyl-1H-1,2,4-triazole-1-ethanol,
α- (5-methyl-1,3-dioxan-5-yl) -β - [[4- (trifluoromethyl) phenyl] methylene] -1H-1,2,4-triazol-1-ethanol,
(5RS, 6RS) -6-hydroxy-2,2,7,7-tetramethyl-5- (1H-1,2,4-triazol-1-yl) -3-octanone,
(E) -α- (methoxyimino) -N-methyl-2-phenoxy-phenylacetamide,
1- (2,4-dichlorophenyl) -2- (1H-1,2,4-triazol-1-yl) -ethanone-O- (phenylmethyl) oxime,
1- (2-methyl-1-naphthalenyl) -1H-pyrrole-2,5-dione,
1- (3,5-dichlorophenyl) -3- (2-propenyl) -2,5-pyrrolidinedione,
1 - [(diiodomethyl) sulfonyl] -4-methyl benzene,
1 - [[2- (2,4-dichlorophenyl) -1,3-dioxolan-2-yl] methyl] -1H-imidazole,
1 - [[2- (4-chlorophenyl) -3-phenyloxiranyl] methyl] -1H-1,2,4-triazole,
1- [1- [2 - [(2,4-dichlorophenyl) methoxy] phenyl] ethenyl] -1H-imidazole,
1-methyl-5-nonyl-2- (phenylmethyl) -3-pyrrolidinol,
2 ', 6'-dibromo-2-methyl-4'-trifluoromethoxy-4'-trifluoromethyl-1,3-thiazole-5-carboxanilide,
2,6-dichloro-5- (methylthio) -4-pyrimidinyl thiocyanate,
2,6-dichloro-N- (4-trifluoromethylbenzyl) -benzamide,
2,6-dichloro-N - [[4- (trifluoromethyl) phenyl] methyl] benzamide,
2- (2,3,3-triiodo-2-propenyl) -2H-tetrazole,
2 - [(1-methylethyl) sulphonyl] -5- (trichloromethyl) -1,3,4-thiadiazole,
2 - [[6-Deoxy-4-O- (4-O-methyl-β-D-glycopyranosyl) -α-D-glucopyranosyl] amino] -4- methoxy-1H-pyrrolo [2,3-d] pyrimidine-5-carbonitrile,
2-aminobutane,
2-bromo-2- (bromomethyl) -pentandinitril,
2-chloro-N- (2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl) -3-pyridine carboxamide,
2-chloro-N- (2,6-dimethylphenyl) -N- (isothiocyanatomethyl) -acetamide,
2-phenylphenol (OPP),
3,4-dichloro-1- [4- (difluoromethoxy) phenyl] -1H-pyrrole-2,5-dione,
3,5-dichloro-N- [cyano [(1-methyl-2-propynyl) -oxy] -methyl] -benzamide,
3- (1,1-dimethylpropyl-1-oxo-1H-indene-2-carbonitrile,
3- [2- (4-chlorophenyl) -5-ethoxy-3-isoxazolidinyl] -pyridine,
4-chloro-2-cyano-N, N-dimethyl-5- (4-methylphenyl) -1H-imidazol-1-sulfonamide,
4-methyl-tetrazolo [1,5-a] quinazolin-5 (4H) -one,
8-hydroxyquinoline sulfate,
9H-xanthene-9-carboxylic acid 2 - [(phenylamino) carbonyl] hydrazide,
bis (1-methylethyl) -3-methyl-4 - [(3-methylbenzoyl) oxy] -2,5-thiophene dicarboxylate,
cis-1- (4-chlorophenyl) -2- (1H-1,2,4-triazol-1-yl) cycloheptanol,
cis-4- [3- [4- (1,1-dimethylpropyl) -phenyl-2-methylpropyl] -2,6-dimethyl-morpholine,
Ethyl - [(4-chlorophenyl) azo] cyanoacetate,
potassium bicarbonate,
Methantetrathiol sodium salt,
Methyl-1- (2,3-dihydro-2,2-dimethyl-1H-inden-1-yl) -1H-imidazole-5-carboxylate,
Methyl-N- (2,6-dimethylphenyl) -N- (5-isoxazolylcarbonyl) -DL-alaninate,
Methyl N- (chloroacetyl) -N- (2,6-dimethylphenyl) -DL-alaninate,
N- (2,6-dimethylphenyl) -2-methoxy-N- (tetrahydro-2-oxo-3-furanyl) acetamide,
N- (2,6-dimethylphenyl) -2-methoxy-N- (tetrahydro-2-oxo-3-thienyl) acetamide,
N- (2-chloro-4-nitrophenyl) -4-methyl-3-nitro-benzenesulfonamide,
N- (4-Cyclohexylphenyl) -1,4,5,6-tetrahydro-2-pyrimidinamine,
N- (4-hexylphenyl) -1,4,5,6-tetrahydro-2-pyrimidinamine,
N- (5-chloro-2-methylphenyl) -2-methoxy-N- (2-oxo-3-oxazolidinyl) -acetamide,
N- (6-methoxy) -3-pyridinyl) -cyclopropanecarboxamide,
N- [2,2,2-trichloro-1 - [(chloroacetyl) -amino] -ethyl] -benzamide,
N- [3-chloro-4,5-bis- (2-propynyloxy) -phenyl] -N'-methoxy-methanimidamid,
N-formyl-N-hydroxy-DL-alanine-sodium salt,
O, O-diethyl [2- (dipropylamino) -2-oxoethyl] -ethylphosphoramidothioat,
O-methyl-S-phenyl-phenylpropylphosphoramidothioate,
S-Methyl-1,2,3-benzothiadiazole-7-carbothioate,
spiro [2H] -1-benzopyran-2,1 '(3'H) -isobenzofuran] -3'-one,
4- (3,4-dimethoxyphenyl) -3- (4-fluorophenyl) acryloyl] morpholine bactericidal bronopol, dichlorophene, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furan carboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam and others, copper sulfate copper preparations. Insecticides / Acaricides / Nematicides Abamectin, Acephate, Acetamiprid, Acrinathrin, Alanycarb, Aldicarb, Aldoxycarb, Alpha-cypermethrin, Alphamethrin, Amitraz, Avermectin, AZ 60541, Azadirachtin, Azamethiphos, Azinphos M, Azinphos M,
Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillus thuringiensis, Baculoviruses, Beauveria bassiana, Beauveria tenella, Bendiocarb, Benfuracarb, Bensultap, Benzoximate, Betacyfluthrin, Bifenazate, Bifenthrin, Bioethanomifhrin, Bethenomifhrin, Bethenomifhrin, Bethanomifhrin , Butocarboxime, butylpyridaben,
Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, Chloethocarb, Chlorethoxyfos, Chlorfenapyr, Chlorfenvinphos, Chlorfluazuron, Chlormephos, Chlorpyrifos, Chlorpyrifos M, Chlovaporthrin, Chromafenozide, Cis-Resmethrin, Clofocytoprene, Cofocenthrin, Cofocenthrin, Cofocenthrin, Cofocenthrin , Cycloprothrin, cyfluthrin, cyhalothrin, cyhexatin, cypermethrin, cyromazine,
Deltamethrin, Demeton M, Demeton S, Demeton-S-methyl, Diafenthiuron, Diazinon, Dichlorvos, Dicofol, Diflubenzuron, Dimethoat, Dimethylvinphos, Diofenolan, Disulfoton, Docusat-sodium, Dofenapyn,
Eflusilanate, Emamectin, Empenthrin, Endosulfan, Entomopfthora spp., Esfenvalerate, Ethiofencarb, Ethion, Ethoprophos, Etofenprox, Etoxazole, Etrimfos,
Fenamiphos, Fenazaquin, Fenbutatin oxide, Fenitrothion, Fenothiocarb, Fenoxacrim, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyrithrin, Fenpyroximate, Fenvalerate, Fipronil, Fluazuron, Flubrocythrinate, Flucycloxuron, Flytoxhrhrininate, Fumetoxinhrinate, Foncythrinate, Foncythrinate, Foncythrinate, Foncythrininate, Fonetoxin , Furathiocarb,
granulosis
Halofenozide, HCH, Heptenophos, Hexaflumuron, Hexythiazox, Hydroprene,
Imidacloprid, indoxacarb, isazofos, isofenphos, isoxathion, ivermectin,
Nuclear polyhedron viruses, lambda cyhalothrin, lufenuron,
Malathion, Mecarbam, Metaldehyde, Methamidophos, Metharhician anisopliae, Metharhician flavoviride, Methidathione, Methiocarb, Methoprene, Methomyl, Methoxyfenozide, Metolcarb, Metoxadiazone, Mevinphos, Milbemectin, Milbemycin, Monocrotophos,
Naled, Nitenpyram, Nithiazine, Novaluron
Omethoate, oxamyl, oxydemethone M
Paecilomyces fumosoroseus, Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalone, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos A, Pirimiphos M, Profenofos, Promecarb, Propargite, Propoxur, Prothiofos, Prothrohrinos, Pothrohrinos, Pothrohrinos, Pothrohrinos , Pyridaben, pyridathione, pyrimidifen, pyriproxyfen,
Quinalphos, ribavirin,
Salithion, Sebufos, Silafluofen, Spinosad, Spirodiclofen, Sulfotep, Sulprofos,
Tau-fluvalinate, tebufenozide, tebufenpyrad, Tebupirimiphos, teflubenzuron, tefluthrin, temephos, Temivinphos, terbufos, tetrachlorvinphos, tetradifon Thetacypermethrin, thiacloprid, thiamethoxam, Thiapronil, Thiatriphos, thiocyclam hydrogen oxalate, thiodicarb, thiofanox, thuringiensin, Tralocythrin, tralomethrin, triarathene, Triazamate , Triazophos, triazuron, trichlophenidines, trichlorfon, triflumuron, trimethacarb,
Vamidothion, Vaniliprole, Verticillium lecanii
YI 5302, zeta-cypermethrin, zolaprofos
(1R-cis) - [5- (phenylmethyl) -3-furanyl] methyl-3 - [(dihydro-2-oxo-3 (2H) - furanylidene) methyl] -2,2-dimethylcyclopropane carboxylate
(3-phenoxyphenyl) methyl-2,2,3,3-tetramethylcyclopropanecarboxylat
1 - [(2-Chloro-5-thiazolyl) methyl] tetrahydro-3,5-dimethyl-N-nitro-1,3,5-triazine-2 (1H) - imine
2- (2-chloro-6-fluorophenyl) -4- [4- (1,1-dimethylethyl) phenyl] -4,5-dihydro-oxazol
2- (Acetlyoxy) -3-dodecyl-1,4-naphthalenedione
2-chloro-N - [[[4- (1-phenylethoxy) phenyl] amino] carbonyl] -benzamide
2-chloro-N - [[[4- (2,2-dichloro-1,1-difluoroethoxy) phenyl] amino] carbonyl] -benzamide
3-methylphenyl propylcarbamate
4- [4- (4-ethoxyphenyl) -4-methylpentyl] -1-fluoro-2-phenoxy-benzene
4-Chloro-2- (1,1-dimethylethyl) -5 - [[2- (2,6-dimethyl-4-phenoxyphenoxy) ethyl] thio] - 3 (2H) pyridazinone
4-chloro-2- (2-chloro-2-methylpropyl) -5 - [(6-iodo-3-pyridinyl) methoxy] -3 (2H) - pyridazinone
4-chloro-5 - [(6-chloro-3-pyridinyl) methoxy] -2- (3,4-dichlorophenyl) -3 (2H) -pyridazinone
Bacillus thuringiensis strain EG-2348
Benzoic acid [2-benzoyl-1- (1,1-dimethylethyl) hydrazide
Butanoic acid 2,2-dimethyl-3- (2,4-dichlorophenyl) -2-oxo-1-oxaspiro [4.5] dec-3-en-4-yl ester
[3 - [(6-chloro-3-pyridinyl) methyl] -2-thiazolidinylidene] -cyanamide
Dihydro-2- (nitromethylene) -2H-1,3-thiazine-3 (4H) -carboxaldehyde
Ethyl [2 - [[1,6-dihydro-6-oxo-1- (phenylmethyl) -4-pyridazinyl] oxy] ethyl] carbamate
N- (3,4,4-trifluoro-1-oxo-3-butenyl) -glycine
N- (4-chlorophenyl) -3- [4- (difluoromethoxy) phenyl] -4,5-dihydro-4-phenyl-1H-pyrazole-1-carboxamide
N - [(2-chloro-5-thiazolyl) methyl] -N'-methyl-N "-nitro-guanidine
N-methyl-N '- (1-methyl-2-propenyl) -1,2-hydrazindicarbothioamid
N-methyl-N'-2-propenyl-1,2-hydrazindicarbothioamid
O, O-diethyl [2- (dipropylamino) -2-oxoethyl] -ethylphosphoramidothioat
N-cyanomethyl-4-trifluoromethyl-nicotinamide
3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- [3- (5-trifluoromethylpyridin-2-yloxy) propoxy] benzene

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

In addition, the compounds of the formula (I) according to the invention also very good antifungal effects. They have a very broad one antifungal activity spectrum, especially against dermatophytes and fungi, Mold and diphasic fungi (e.g. against Candida species such as Candida albicans, Candida glabrata) and Epidermophyton floccosum, Aspergillus species such as Aspergillus niger and Aspergillus fumigatus, Trichophyton species such as Trichophyton mentagrophytes, Microsporon species like Microsporon canis and audouinii. The The list of these mushrooms in no way places a restriction on what can be detected mycotic spectrum, but is only explanatory.

The active substances can be used as such, in the form of their formulations or in the form thereof prepared application forms, such as ready-to-use solutions, suspensions, Spray powder, pastes, soluble powders, dusts and granules can be used. 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 Apply active ingredients according to the ultra-low-volume process or Active ingredient preparation or to inject the active ingredient yourself into the soil. It can also do that Seeds of the plants are treated.

When using the active compounds according to the invention as fungicides, the Application rates can be varied within a wide range depending on the type of application.

When treating parts of plants, the amounts of active ingredient are in the generally between 0.1 and 10,000 g / ha, preferably between 10 and 1,000 g / ha. In the case of seed treatment, the active compound application rates are in general between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed. In the treatment of the soil Application rates of active ingredient in general between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g / ha.

As already mentioned above, according to the invention all plants and their parts can be treated. In a preferred embodiment, go wild occurring or by conventional organic breeding methods, such as crossing or Protoplast fusion obtained plant species and plant varieties and their parts treated. In a further preferred embodiment, transgenic plants and Plant varieties that may be in genetic engineering methods Combination with conventional methods were obtained (Genetic Modified Organisms) and treated their parts. The term "parts" or "parts of plants" or "Plant parts" was explained above.

Plants of the commercially available in each case are particularly preferred according to the invention or plant varieties in use. Among plant varieties is understood to mean plants with new properties ("traits") that are characterized by both conventional breeding, by mutagenesis or by recombinant DNA techniques have been bred. These can be varieties, breeds, bio and genotypes.

Depending on the plant species or plant varieties, their location and Growth conditions (soils, climate, growing season, nutrition) can be determined by the Treatment according to the invention also results in superadditive (“synergistic”) effects. So are, for example, reduced application rates and / or extensions of the Spectrum of activity and / or an enhancement of the effect of the invention usable substances and agents, better plant growth, increased tolerance against high or low temperatures, increased tolerance to drought or against water or soil salt content, increased flowering performance, easier harvesting, Acceleration of ripeness, higher crop yields, higher quality and / or higher Nutritional value of the harvested products, higher shelf life and / or workability of the harvested products possible, which have the expected effects go out.

Among the preferred transgenes to be treated according to the invention (Genetically engineered) plants or plant varieties include all plants that are affected by the genetic engineering modification received genetic material that this Gives plants special beneficial valuable properties ("traits"). Examples for such properties are better plant growth, increased tolerance against high or low temperatures, increased tolerance to drought or against water or soil salt content, increased flowering performance, easier harvesting, Acceleration of ripeness, higher crop yields, higher quality and / or higher Nutritional value of the harvested products, higher shelf life and / or workability of the Harvested products. Further and particularly highlighted examples of such Properties are an increased defense of the plants against animal and microbial Pests, such as against insects, mites, phytopathogenic fungi, bacteria and / or viruses and an increased tolerance of the plants to certain herbicides Agents. The important cultivated plants, such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, rapeseed and Fruit plants (with the fruits apples, pears, citrus fruits and grapes) mentioned, corn, soybeans, potatoes, cotton and rapeseed are particularly emphasized. The increased defense is particularly emphasized as traits of plants against insects by toxins arising in the plants, in particular those which are caused by the genetic material from Bacillus Thuringiensis (e.g. by the Gene CryIA (a), CryIA (b), CryIA (c), CryIIA, CryIIIA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CryIF and their combinations) are generated in the plants (in following "Bt plants"). As properties ("traits") are also special highlighted the increased defense of plants against fungi, bacteria and viruses through systemic acquired resistance (SAR), systemin, phytoalexins, elicitors as well as resistance genes and correspondingly expressed proteins and toxins. As Properties ("traits") continue to be particularly emphasized the increased Plant tolerance to certain herbicidal active ingredients, for example Imidazolinones, sulfonylureas, glyphosate or phosphinotricin (e.g. "PAT" - Gene). The genes that confer the desired traits can also occur in combinations with one another in the transgenic plants. Examples of "Bt plants" are maize, cotton, soybean and Called potato varieties that are sold under the trade names YIELD GARD® (e.g. Corn, cotton, soy), KnockOut® (e.g. corn), StarLink® (e.g. corn), Bollgard® (Cotton), Nucoton® (cotton) and NewLeaf® (potato). Examples of herbicide-tolerant plants are maize, cotton and Soybeans known as Roundup Ready® (tolerance against glyphosate e.g. B. corn, cotton, soy), Liberty Link® (tolerance against Phosphinotricin, e.g. Rape), IMI® (tolerance to imidazolinones) and STS® (Tolerance to sulfonylureas e.g. maize). As a herbicide resistant (conventionally grown to herbicide tolerance) plants are also the varieties sold under the name Clearfield® (e.g. maize). Of course, these statements also apply to future developed or future plant varieties with these or in the future developed genetic traits.

The plants listed can be particularly advantageous according to the invention with the Compounds of the general formulas (I), (Ia), (Ib), (Ic), (Id) and (Ie) and the Active substance mixtures according to the invention are treated. The two Active ingredients or mixtures specified above also apply to the Treatment of these plants. The plant treatment is particularly emphasized the compounds or mixtures specifically listed in the present text.

The manufacture and use of the substances according to the invention are based on following examples.

Preparation Examples example 1

Procedure A)

0.288 g (1.3 mmol) of 3'-chloro-4'-fluoro-1,1'-biphenyl-2-amine are added in 3 ml Dissolved tetrahydrofuran, with 0.36 ml (2.6 mmol) triethylamine and 0.25 g (1.56 mmol) 2- Trifluoromethylbenzoic acid chloride (dissolved in 3 ml of tetrahydrofuran) was added. The Reaction solution is stirred at 60 ° C for 16 h. To work up concentrated and the crude product by means of column chromatography (Cyclohexane / ethyl acetate 2: 1) cleaned.

0.491 g (96% of theory) of N- (3'-chloro-4'-fluoro-1,1'-biphenyl-2-yl) -2- (trifluoromethyl) benzamide (compound 35, see Table 1) are obtained. with the logP (pH 2.3) = 3.81. Example 2

Procedure D)

226 mg (1.1 mmol) of 2-chloro-5-bromotoluene are dissolved with 245 mg (2.5 mmol) of potassium acetate and 279 mg (1.1 mmol) of pinacoldiboronic ester in 8 ml of dimethylformamide (if possible free of oxygen) and with a catalytic amount (0.1 eq.) PdCl ₂ (dppf) added. The reaction mixture is stirred for 2 h at 80-90 ° C and after cooling with 5 eq. 2 M sodium carbonate solution, 344 mg (1.0 mmol) of the N- (2-bromophenyl) -2- (trifluoromethyl) benzamide (dissolved in 4 ml of dimethylformamide) and a further 0.1 eq. Catalyst added. The reaction solution is stirred at 80-90 ° C for 16 h. For working up, 2 ml of water and 8 ml of ethyl acetate are added. The organic phase is concentrated and purified by means of column chromatography (cyclohexane / ethyl acetate 1: 1).

151 mg (39% of theory) of N- (4'-chloro-3'-methyl-1,1'-biphenyl-2-yl) -2- are obtained. (trifluoromethyl) benzamide (compound 42, see Table 1) with the logP (pH 2.3) = 4.18.

The compounds of the formula (I) listed in Table 1 below can be obtained analogously to Examples 1 and 2 and in accordance with the general descriptions of processes A) to D) according to the invention. The last column of the table shows the group of new compounds according to the invention to which the respective substance belongs. Table 1





Preparation of starting materials of the formula (III) Example (III-1)

Under an argon atmosphere, 38.8 g (223 mmol) of the 3-chloro-4-fluorophenylboronic acid, 40.6 g (186 mmol) 2-iodoaniline in 220 ml toluene, 22 ml ethanol and 45 ml a 4 M sodium hydrogen carbonate solution. 4.3 g (4 mmol) Tetrakis (triphenylphosphine) palladium (0) are added and the reaction solution for 2-16 h Heated to 80 ° C. For working up, the phases are separated, the organic phase dried over magnesium sulfate and concentrated. The cleaning of the Crude product is carried out by column chromatography (Cyclohexane / ethyl acetate 3: 1) and / or by recrystallization.

19.8 g (48% of theory) of 3'-chloro-4'-fluoro-1,1'-biphenyl-2-amine are obtained with the logP (pH 2.3) = 3.01. Production of starting materials of the formula (IV) Example (IV-1)

7.5 g (0.044 mol) of 2-bromoaniline are placed in 100 ml of acetonitrile and consecutively with 7.8 g (0.057 mol) potassium carbonate and 10.0 g (0.048 mol) 2-trifluoromethylbenzoic acid chloride added. The reaction solution is under for 16 h Reflux heated. For working up, concentrate and with Chromatographed cyclohexane / ethyl acetate on silica gel.

9.75 g (65% of theory) of N- (2-bromophenyl) -2- (trifluoromethyl) benzamide are obtained with the logP (pH 2.3) = 2.99.

The determination of those in the tables and manufacturing examples above specified logP values are carried out in accordance with EEC Directive 79/831 Annex V.48 HPLC (High Performance Liquid Chromatography) on a phase reversal column (C18). Temperature: 43 ° C.

The determination is carried out in the acidic range at pH 2.3 with 0.1% aqueous Phosphoric acid and acetonitrile as eluents; linear gradient of 10% acetonitrile up to 90% acetonitrile.

The calibration takes place with unbranched alkan-4-ones (with 3 to 16 Carbon atoms) whose logP values are known (determination of the logP values using the Retention time by linear interpolation between two successive ones Alkanones).

applications Example A Podosphaera test (apple) / protective

Solvent:

24.5 parts by weight of acetone

24.5 parts by weight of dimethylacetamide

emulsifier:

1.0 part by weight of alkyl aryl polyglycol ether

To prepare 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.

Young plants are tested with the Active ingredient preparation sprayed in the application rate specified. After the The plants are sprayed with an aqueous spore suspension of Powdery mildew pathogen Podosphaera leucotricha inoculated. The plants are then in the Greenhouse set up at approx. 23 ° C and a relative humidity of approx. 70%.

Evaluation is carried out 10 days after the inoculation. 0% means a Efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.

Active substances, application rates and test results are shown in the following table. Table A Podosphaera test (apple) / protective

Table A Podosphaera test (apple) / protective

Table A Podosphaera test (apple) / protective

Example B Sphaerotheca test (cucumber) / protective

Solvent:

24.5 parts by weight of acetone

24.5 parts by weight of dimethylacetamide

emulsifier:

1.0 part by weight of alkyl aryl polyglycol ether

To prepare 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.

Young plants are tested with the Active ingredient preparation sprayed in the application rate specified. After the The plants are sprayed with an aqueous spore suspension of Sphaerotheca fuliginea inoculated. The plants are then at about 23 ° C and one relative humidity of about 70% in the greenhouse.

Evaluation is carried out 7 days after the inoculation. 0% means a Efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.

Active substances, application rates and test results are shown in the following table. Table B Sphaerotheca test (cucumber) / protective

Table B Sphaerotheca test (cucumber) / protective

Example C Venturia test (apple) / protective

Solvent:

24.5 parts by weight of acetone

24.5 parts by weight of dimethylacetamide

emulsifier:

1.0 part by weight of alkyl aryl polyglycol ether

To prepare 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.

Young plants are tested with the Active ingredient preparation sprayed in the application rate specified. After the The plants are sprayed with an aqueous conidia suspension of Apple scab pathogen Venturia inaequalis and then remain at about 20 ° C for 1 day and 100% relative humidity in an incubation cabin.

The plants are then in a greenhouse at about 21 ° C and a relative Air humidity of approx. 90% set up.

Evaluation is carried out 10 days after the inoculation. 0% means a Efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.

Active substances, application rates and test results are shown in the following table. Table C Venturia test (apple) / protective

Table C Venturia test (apple) / protective

Example D Pyrenophora teres test (barley) / protective

Solvent:

25 parts by weight of N, N-dimethylacetamide

emulsifier:

0.6 parts by weight of alkylaryl polyglycol ether

To prepare 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.

Young plants are tested with the Active ingredient preparation sprayed in the application rate specified. After the The plants are sprayed with a conidia suspension of Pyrenophora teres sprayed. The plants remain at 20 ° C and 100% relative for 48 hours Humidity in an incubation cabin.

The plants are then grown in a greenhouse at a temperature of approximately 20 ° C and relative humidity of approx. 80%.

Active substances, application rates and test results are shown in the following table. Table D Pyrenophora teres test (barley) / protective

Example E Alternaria test (tomato) / protective

Solvent:

49 parts by weight of N, N-dimethylformamide

emulsifier:

1 part by weight of alkylaryl polyglycol ether

To prepare 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 tomato plants are sprayed with the active ingredient preparation in the application rate specified. 1 day after the The plants are treated with a spore suspension of Alternaria solani inoculated and then stand for 24 h at 100% relative humidity and 20 ° C. Subsequently the plants are at 96% relative humidity and a temperature of 20 ° C.

Evaluation is carried out 7 days after the inoculation. 0% means a Efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.

Active substances, application rates and test results are shown in the following table. Table E Alternaria test (tomato) / protective

Claims (17)

1. Microbicidal agents, characterized in that they contain at least one biphenylbenzamide derivative of the formula (I)


in which
R ^{1 represents} methyl, trifluoromethyl, chlorine, bromine or iodine,
R ^{2 represents} hydrogen or fluorine,
R ³ for halogen, cyano, nitro, C ₁ -C ₆ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylsulfonyl, C ₂ -C ₆ alkenyl, C ₃ -C ₆ cycloalkyl, or represents C ₁ -C ₆ haloalkyl, C ₁ -C ₆ haloalkoxy, C ₁ -C ₆ haloalkylthio or C ₁ -C ₆ haloalkylsulfonyl each having 1 to 13 halogen atoms,
m represents 1, 2, 3, 4 or 5, it being possible for the radicals R ^{3 to be the} same or different if m is 2, 3, 4 or 5,
for combating phytopathogenic pathogens of the classes Chytridiomycetes, Zygomycetes, Hemiascomycetes, Plectomycetes, Pyrenomycetes, Pyrenomycetes, Laboulbeniomycetes, Locoloascomycetes, Basidiomycetes and Deuteromycetes, as well as harmful microorganisms in the protection of materials such as Pseudomonobaceaeaeaeaeae, Pseudomonobactereaeaeaeae, Pseudomonobaceaeeaceae 2. Composition according to claim 1, characterized by a content of at least one biphenylbenzamide derivative of the formula (I) in which
R ^{1 represents} trifluoromethyl, chlorine, bromine or iodine,
R ^{2 represents} hydrogen or fluorine,
R ³ for halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₂ -C ₄ alkenyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or for C ₁ - C ₄ haloalkyl, C ₁ -C ₄ haloalkoxy or C ₁ -C ₄ haloalkylthio each having 1 to 9 halogen atoms,
m stands for 1, 2, 3, where the radicals R ^{3 can be the} same or different if m stands for 2 or 3. 3. Composition according to claim 1, characterized by a content of at least one biphenylbenzamide derivative of the formula (I) in which
R ^{1 represents} trifluoromethyl or iodine,
R ^{2 represents} hydrogen,
R ³ for fluorine, chlorine, bromine, iodine, methyl, ethyl, n-, i-propyl, n-, i-, s-, t-butyl, methoxy, ethoxy, methylthio, ethylthio, or for C ₁ -C ₂ Haloalkyl, C ₁ -C ₂ haloalkoxy or C ₁ -C ₂ haloalkylthio each having 1 to 5 halogen atoms,
m stands for 1, 2, where the radicals R ^{3 can be the} same or different if m stands for 2. 4. Composition according to claim 1, characterized by a content of at least one biphenylbenzamide derivative of the formula (I) in which
R ^{1 represents} trifluoromethyl or iodine,
R ^{2 represents} hydrogen,
R ^{3 represents} fluorine, chlorine, bromine, methyl, methoxy, methylthio, trifluoromethyl, trifluoromethoxy or trifluoromethylthio,
m stands for 1, 2, where the radicals R ^{3 can be the} same or different if m stands for 2. 5. Composition according to one or more of claims 1 to 4, for combating of Xanthomonas species, such as, for example, Xanthomonas campestris pv. oryzae; Pseudomonas species, such as, for example, Pseudomonas syringae pv. lachrymans; Erwinia species, such as, for example, Erwinia amylovora; Erysiphe Species such as Erysiphe graminis; Sphaerotheca species, such as for example Sphaerotheca fuliginea; Podosphaera species, such as Podosphaera leucotricha; Venturia species, such as, for example, Venturia inaequalis; Pyrenophora species, such as, for example, Pyrenophora teres or P. graminea (conidial form: Drechslera, Syn: Helminthosporium); Cochliobolus Species, such as Cochliobolus sativus (conidial form: Drechslera, 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; Pellicularia species, such as for example Pellicularia sasakii; Pyricularia species, such as, for example, Pyricularia oryzae; Fusarium species, such as, for example, Fusarium culmorum; Septoria Species such as Septoria nodorum; Leptosphaeria species, such as for example Leptosphaeria nodorum; Cercospora species, such as Cercospora canescens; Alternaria species, such as, for example, Alternaria brassicae; Pseudocercosporella species, such as, for example, Pseudocercosporella herpotrichoides. 6. A method for controlling undesirable microorganisms Claim 1, characterized in that the biphenylbenzamide derivatives Formula (I) according to claim 1 to the microorganisms and / or their Brings out living space. 7. A method for producing microbicidal agents, characterized in that that with biphenylbenzamide derivatives of formula (I) according to claim 1 Extenders and / or surfactants mixed. 8. Biphenylbenzamide derivatives of the formulas (Ia)


in which
R ^{1 represents} methyl, trifluoromethyl, chlorine, bromine or iodine,
R ^{2 represents} hydrogen or fluorine,
R ³ for halogen, cyano, nitro, C ₁ -C ₆ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylsulfonyl, C ₂ -C ₆ alkenyl, C ₃ -C ₆ cycloalkyl, or C ₁ -C ₆ haloalkyl, C ₁ -C ₆ haloalkoxy, C ₁ -C ₆ haloalkylthio or C ₁ -C ₆ haloalkylsulfonyl, each with 1 to 13 halogen atoms,
n represents 2, 3, 4 or 5, where the radicals R ^{3 may be the} same or different. 9. biphenylbenzamide derivatives of the formula (Ia) according to claim 8, in which
R ^{1 represents} trifluoromethyl, chlorine, bromine or iodine,
R ^{2 represents} hydrogen or fluorine,
R ³ for halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₂ -C ₄ alkenyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or for C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -haloalkoxy or C ₁ -C ₄ -haloalkylthio each having 1 to 9 halogen atoms,
n represents 2, 3, where the radicals R ^{3 may be the} same or different. 10. Biphenylbenzamide derivatives of the formula (Ib)


in which
R ^{1 represents} methyl, trifluoromethyl, chlorine, bromine or iodine,
R ^{20 represents} fluorine,
R ³ for halogen, cyano, nitro, C ₁ -C ₆ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylsulfonyl, C ₂ -C ₆ alkenyl, C ₃ -C ₆ cycloalkyl, or represents C ₁ -C ₆ haloalkyl, C ₁ -C ₆ haloalkoxy, C ₁ -C ₆ haloalkylthio or C ₁ -C ₆ haloalkylsulfonyl each having 1 to 13 halogen atoms,
m represents 1, 2, 3, 4 or 5, where the radicals R ^{3 can be the} same or different if m represents 2, 3, 4 or 5. 11. biphenylbenzamide derivatives of the formula (Ib) according to claim 10, in which
R ^{1 represents} trifluoromethyl, chlorine, bromine or iodine,
R ^{20 represents} fluorine,
R ³ for halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₂ -C ₄ alkenyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or for C ₁ - C ₄ haloalkyl, C ₁ -C ₄ haloalkoxy or C ₁ -C ₄ haloalkylthio each having 1 to 9 halogen atoms,
m stands for 1, 2, 3, where the radicals R ^{3 can be the} same or different if m stands for 2 or 3. 12. Biphenylbenzamide derivatives of the formulas (Ic), (Id) and (Ie)




in which each
R ^{1 represents} methyl, trifluoromethyl, chlorine, bromine or iodine,
R ^{2 represents} hydrogen or fluorine,
R ³¹ , R ³² and R ³³ independently of one another for halogen, cyano, nitro, C ₁ -C ₆ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylsulfonyl, C ₂ -C ₆ alkenyl, C ₃ -C ₆ cycloalkyl, or for C ₁ -C ₆ haloalkyl, C ₁ -C ₆ haloalkoxy, C ₁ -C ₆ haloalkylthio or C ₁ -C ₆ haloalkylsulfonyl, each with 1 to 13 halogen atoms,
with the proviso that R ³¹ and R ^{33 are} each not fluorine if R ^{1 is} trifluoromethyl and R ^{2 is} hydrogen. 13. Biphenylbenzamide derivatives of the formulas (Ic), (Id) and (Ie) according to claim 12, in each of which
R ^{1 represents} trifluoromethyl, chlorine, bromine or iodine,
R ^{2 represents} hydrogen or fluorine,
R ³¹ , R ³² and R ³³ independently of one another for halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₂ -C ₄ alkenyl, cyclopropyl, cyclobutyl, cyclopentyl , Cyclohexyl, or C ₁ -C ₄ haloalkyl, C ₁ -C ₄ haloalkoxy or C ₁ -C ₄ haloalkylthio each having 1 to 9 halogen atoms,
with the proviso that R ³¹ and R ^{33 are} each not fluorine if R ^{1 is} trifluoromethyl and R ^{2 is} hydrogen. 14. Means for controlling unwanted microorganisms, characterized by containing at least one biphenylbenzamide derivative Formula (Ia) according to claim 8, (Ib) according to claim 10, (Ic), (Id) and / or (Ie) according to claim 12 in addition to extenders and / or surface-active Substances. 15. Use of biphenylbenzamide derivatives of the formula (Ia) according to Claim 8, (Ib) according to claim 10, (Ic), (Id) and (Ie) according to claim 12 for Combat unwanted microorganisms. 16. A method for controlling unwanted microorganisms, thereby characterized in that biphenylbenzamide derivatives of the formula (Ia) according to Claim 8, (Ib) according to claim 10, (Ic), (Id) and / or (Ie) according to Claim 12 to the microorganisms and / or their habitat. 17. A method of making undesirable agents Microorganisms, characterized in that biphenylbenzamide Derivatives of the formula (Ia) according to Claim 8, (Ib) according to Claim 10, (Ic), (Id) and / or (Ie) with extenders and / or surface-active substances mixed.