KR20060017605A - Difluoromethylbenzanilides and use thereof for combating micro-organisms, intermediate products and use thereof - Google Patents

Abstract

The invention relates to novel difluoromethylbenzanilides of formula (I), wherein R1, R 2, R3, R4, R5and Z have the meanings cited in the description. The invention also relates to several methods for the production of said substances and the use thereof in order to combat undesired micro-organisms, and to novel intermediate products and the use thereof.

Description

Difluoromethylbenzanilides, their use to control microorganisms, intermediate products and their use {Difluoromethylbenzanilides and use about for combating micro-organisms, intermediate products and use about}

The present invention relates to novel difluoromethylbenzanilides, a number of methods for their preparation and their use for controlling unwanted microorganisms.

It is already known that many carboxanilides have fungicidal properties (see, eg, EP-A 0 545 099, JP-A 2001-302605, JP-A 8-176112). That is, N- (4'-fluoro-1,1'-biphenyl-2-yl) -2- (trifluoromethyl) benzamide and N- (2-sec-butylphenyl) -2- (tri Fluoromethyl) benzamides are known from EP-A 0 554 099. The activity of these compounds is good; In some cases, for example, it is not satisfactory at low application rates. Difluoromethylbenzanilide is not known yet.

The present invention provides novel difluoromethylbenzanilides of general formula (I):

Where

R ¹ , R ² , R ³ and R ⁴ independently of one another represent hydrogen, fluorine, chlorine, methyl, isopropyl or methylthio,

R ⁵ is hydrogen, C ₁ -C ₈ -alkyl, C ₁ -C ₆ -alkylsulfinyl, C ₁ -C ₆ -alkylsulfonyl, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, C ₃ -C ₈ -cycloalkyl; Having 1 to 9 fluorine, chlorine and / or bromine atoms in each case C ₁ -C ₆ - haloalkyl, C ₁ -C ₄ - haloalkylthio, C ₁ -C ₄ - haloalkyl sulfinyl, C ₁ - C ₄ -haloalkylsulfonyl, halo-C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl or C ₃ -C ₈ -halocycloalkyl; Formyl-C ₁ -C ₃ -alkyl, (C ₁ -C ₃ -alkyl) carbonyl-C ₁ -C ₃ -alkyl, (C ₁ -C ₃ -alkoxy) carbonyl-C ₁ -C ₃ -alkyl ; (C ₁ -C ₃ -haloalkyl) carbonyl-C ₁ -C ₃ -alkyl or (C ₁ -C ₃ -haloalkoxy) carbonyl having 1 to 7 fluorine, chlorine and / or bromine atoms in each case -C ₁ -C ₃ -alkyl; (C ₁ -C ₃ -alkyl) carbonyl-C ₁ -C ₃ -haloalkyl or (C ₁ -C ₃ -alkoxy) carbonyl- having 1 to 6 fluorine, chlorine and / or bromine atoms in each case C ₁ -C ₃ -haloalkyl; (C ₁ -C ₃ -haloalkyl) carbonyl-C ₁ -C ₃ -haloalkyl or (C ₁ -C ₃ -haloalkoxy) carbo having 1 to 13 fluorine, chlorine and / or bromine atoms in each case Nyl-C ₁ -C ₃ -haloalkyl; -COR ⁶ , -CONR ⁷ R ⁸ or -CH ₂ NR ⁹ R ¹⁰ ,

R ⁶ is hydrogen, C ₁ -C ₈ -alkyl, C ₁ -C ₈ -alkoxy, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, C ₃ -C ₈ -cycloalkyl; In each case 1 to 9 fluorine, C ₁ -C ₆ having a chlorine and / or bromine atoms can roal Kiel, C ₁ -C ₆ - haloalkoxy, halo -C ₁ -C ₄ - alkoxy -C ₁ -C ₄ -alkyl or C ₃ -C ₈ -halocycloalkyl; Or -COR ¹¹ ,

R ⁷ and R ⁸ independently of one another are hydrogen, C ₁ -C ₈ -alkyl, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, C ₃ -C ₈ -cycloalkyl; C ₁ -C ₈ -haloalkyl, halo-C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl or C ₃ -C ₈ -having 1 to 9 fluorine, chlorine and / or bromine atoms in each case Halocycloalkyl, or

R ⁷ and R ⁸ together with the nitrogen atom to which they are attached may contain one or two additional nonadjacent heteroatoms selected from the group consisting of oxygen, sulfur and NR ¹² , halogen and C ₁ -C ₄ -alkyl To form a saturated heterocycle of 5 to 8 reducers, optionally mono- or polysubstituted, by the same or different substituents selected from the group consisting of

R ⁹ and R ¹⁰ are independently of each other hydrogen, C ₁ -C ₈ -alkyl, C ₃ -C ₈ -cycloalkyl; In each case represent C ₁ -C ₈ -haloalkyl or C ₃ -C ₈ -halocycloalkyl having 1 to 9 fluorine, chlorine and / or bromine atoms,

R ⁹ and R ¹⁰ together with the nitrogen atom to which they are attached may contain one or two additional nonadjacent heteroatoms selected from the group consisting of oxygen, sulfur and NR ¹² , and include halogen and C ₁ -C _4- ; To form a saturated heterocycle of 5 to 8 reducers, optionally mono- or polysubstituted, by the same or different substituents selected from the group consisting of alkyl,

R ¹¹ is hydrogen, C ₁ -C ₈ -alkyl, C ₁ -C ₈ -alkoxy, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, C ₃ -C ₈ -cycloalkyl; C ₁ -C ₆ -haloalkyl, C ₁ -C ₆ -haloalkoxy, halo-C ₁ -C ₄ -alkoxy-C ₁ -C ₄ with 1 to 9 fluorine, chlorine and / or bromine atoms in each case -Alkyl or C ₃ -C ₈ -halocycloalkyl;

R ¹² represents hydrogen or C ₁ -C ₆ -alkyl,

Z represents Z ¹ , Z ² , Z ³ or Z ⁴ ,

From here,

Z ¹ represents phenyl optionally mono- to substituted by the same or different substituents,

Z ² represents a bicycloalkyl or cycloalkyl optionally mono- or polysubstituted by the same or different substituents,

Z ³ is unsubstituted C ₂ -C ₂₀ ring - represents an alkyl or halogen and C ₃ -C ₆ - cycloalkyl optionally substituted by identical or different substituents selected from the group consisting of alkyl mono- or multi-substituted C ₁ -C ₂₀ -Alkyl, wherein the cycloalkyl moiety can be optionally mono- or polysubstituted by the same or different substituents selected from the group consisting of halogen and C ₁ -C ₄ -alkyl,

Z ⁴ represents C ₂ -C ₂₀ -alkenyl or C ₂ -C ₂₀ -alkynyl, optionally mono- or polysubstituted by the same or different substituents selected from the group consisting of halogen and C ₃ -C ₆ -cycloalkyl, respectively Wherein the cycloalkyl moiety may be optionally mono- or polysubstituted by the same or different substituents selected from the group consisting of halogen and C ₁ -C ₄ -alkyl,

R ¹ , R ² and R ³ independently of one another represent hydrogen or fluorine,

Z and R ⁴ together with the carbon atom to which they are attached form an optionally substituted 5- or 6-membered carbocyclic or heterocyclic ring.

Further, difluoromethylbenzanilide of general formula (I)

a) General difluoromethylbenzoyl derivatives of the general formula (II) are optionally present in the presence of a catalyst, optionally in the presence of a condensing agent, optionally in the presence of an acid binder and optionally in the presence of a diluent Reacted with the aniline derivative of formula (III), or

b) reacting the halodifluoromethylbenzanilide of formula (IV) with the boronic acid derivative of formula (V) in the presence of a catalyst, optionally in the presence of an acid binder and optionally in the presence of a diluent ,

c) reacting the difluoromethylbenzamide boronic acid derivative of formula (VI) with the phenyl derivative of formula (VII) in the presence of a catalyst, optionally in the presence of an acid binder and optionally in the presence of a diluent Or

d) halodifluoromethylbenzanilide of general formula (IV) in the presence of palladium or nickel catalyst, 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2 Reacting with a phenyl derivative of formula (VII) in the presence of a '-bis-1,3,2-dioxaborolane, optionally in the presence of an acid binder and optionally in the presence of a diluent,

e) hydrogenating difluoromethylbenzanilide of general formula (Ia), optionally in the presence of a diluent and optionally in the presence of a catalyst, or

f) dehydrating hydroxyalkyldifluoromethylbenzanilide of general formula (VIII), optionally in the presence of a diluent and optionally in the presence of an acid,

g) Halogen-difluoromethylbenzanilides of general formula (IV) are optionally substituted with general formula (IX) in the presence of a diluent, optionally in the presence of an acid binder and optionally in the presence of at least one catalyst Reacted with an alkyne or an alkene of formula (X), or

h) reacting a ketone of general formula (XI) with a phosphorus compound of general formula (XII), optionally in the presence of a diluent,

i) It was found that difluoromethylbenzanilide of formula (Ib) is obtained by reacting with a halide of formula (XIII) in the presence of a base and in the presence of a diluent:

Where

R ¹ , R ² , R ³ , R ⁴ , R ⁵ , Z, Z ¹ , R ⁶ , R ⁷ , R ⁸ , R ⁹ and R ¹⁰ are as defined above,

X ¹ represents chlorine or hydroxyl,

X ² represents chlorine, bromine, iodine or trifluoromethylsulfonate,

A ¹ and A ² each represent hydrogen or together represent tetramethylethylene,

A ³ and A ⁴ each represent hydrogen or together represent tetramethylethylene,

X ³ represents chlorine, bromine, iodine or trifluoromethylsulfonate,

X ⁴ represents C ₂ -C ₂₀ -alkenyl or C ₂ -C ₂₀ -alkynyl, optionally mono- or polysubstituted by the same or different substituents selected from the group consisting of halogen and C ₃ -C ₆ -cycloalkyl, respectively Wherein the cycloalkyl moiety may be optionally substituted by halogen and / or C ₁ -C ₄ -alkyl,

X ⁵ represents C ₂ -C ₂₀ -hydroxyalkyl optionally mono- or polysubstituted by the same or different substituents selected from the group consisting of halogen and C ₃ -C ₆ -cycloalkyl, wherein the cycloalkyl moiety is halogen And / or optionally substituted by C ₁ -C ₄ -alkyl,

A ⁵ represents C ₂ -C ₁₈ -alkyl optionally mono- or polysubstituted by the same or different substituents selected from the group consisting of halogen and C ₃ -C ₆ -cycloalkyl, wherein the cycloalkyl moiety is halogen and // Or optionally substituted by C ₁ -C ₄ -alkyl,

A ⁶ , A ⁷ and A ⁸ each independently represent hydrogen, or are optionally mono- or polysubstituted by the same or different substituents selected from the group consisting of halogen and C ₃ -C ₆ -cycloalkyl, and the open chain of the molecule Alkyl of the moiety not exceeding 20, wherein the cycloalkyl moiety may be optionally substituted by halogen and / or C ₁ -C ₄ -alkyl,

A ⁹ represents hydrogen or C ₁ -C ₁₈ -alkyl optionally mono- or polysubstituted by the same or different substituents selected from the group consisting of halogen and C ₃ -C ₆ -cycloalkyl, wherein cycloalkyl Moieties may be optionally substituted by halogen and / or C ₁ -C ₄ -alkyl,

A ¹⁰ represents C ₁ -C ₁₈ -alkyl optionally mono- or polysubstituted by the same or different substituents selected from the group consisting of halogen and C ₃ -C ₆ -cycloalkyl, wherein the cycloalkyl moiety is halogen and // Or optionally substituted by C ₁ -C ₄ -alkyl,

P _x is a group ^{_{-P + (C 6 H 5)}} 3 Cl -, -P + (C 6 H 5) 3 Br -, -P + (C 6 H 5) 3 I -, -P (= O) ( OCH ₃ ) ₃ or -P (= O) (OC ₂ H ₅ ) ₃ ,

R ^5-1 is C ₁ -C ₈ -alkyl, C ₁ -C ₆ -alkylsulfinyl, C ₁ -C ₆ -alkylsulfonyl, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, C ₃ -C ₈ -cycloalkyl; Having 1 to 9 fluorine, chlorine and / or bromine atoms in each case C ₁ -C ₆ - haloalkyl, C ₁ -C ₄ - haloalkylthio, C ₁ -C ₄ - haloalkyl sulfinyl, C ₁ - C ₄ -haloalkylsulfonyl, halo-C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl or C ₃ -C ₈ -halocycloalkyl; Formyl-C ₁ -C ₃ -alkyl, (C ₁ -C ₃ -alkyl) carbonyl-C ₁ -C ₃ -alkyl, (C ₁ -C ₃ -alkoxy) carbonyl-C ₁ -C ₃ -alkyl ; (C ₁ -C ₃ -haloalkyl) carbonyl-C ₁ -C ₃ -alkyl or (C ₁ -C ₃ -haloalkoxy) carbonyl having 1 to 7 fluorine, chlorine and / or bromine atoms in each case -C ₁ -C ₃ -alkyl; (C ₁ -C ₃ -alkyl) carbonyl-C ₁ -C ₃ -haloalkyl or (C ₁ -C ₃ -alkoxy) carbonyl- having 1 to 6 fluorine, chlorine and / or bromine atoms in each case C ₁ -C ₃ -haloalkyl; (C ₁ -C ₃ -haloalkyl) carbonyl-C ₁ -C ₃ -haloalkyl or (C ₁ -C ₃ -haloalkoxy) carbo having 1 to 13 fluorine, chlorine and / or bromine atoms in each case Nyl-C ₁ -C ₃ -haloalkyl; -COR ⁶ , -CONR ⁷ R ⁸ or -CH ₂ NR ⁹ R ¹⁰ ,

X ⁶ represents chlorine, bromine or iodine.

Finally, the novel difluoromethylbenzanilides of general formula (I) have very good microbiality and can be used to control unwanted microorganisms in both crop protection and material protection.

Surprisingly, the difluoromethylbenzanilides of the general formula (I) according to the invention have the same propensity for action and have far superior fungicidal activity than the structurally most similar prior art compounds.

In some cases, the compounds according to the invention may exist as possible different isomers, especially stereoisomers such as E and Z, stereo and erythro and also mixtures of optical isomers and also optionally tautomers. E and Z isomers, and stereo and erythro and also optical isomers, any mixtures of these isomers and possible tautomeric forms are claimed.

Formula (I) provides a general definition of difluoromethylbenzanilides according to the present invention. Hereinafter, definitions of the preferred radicals of the general formulas mentioned above and hereinafter are given. These definitions apply to the final product of formula (I) and correspondingly all intermediates.

R ¹ , R ² , R ³ and R ⁴ independently of one another preferably represent hydrogen, fluorine, chlorine or methyl.

R ¹ particularly preferably represents hydrogen or fluorine,

R ¹ very particularly preferably represents hydrogen,

R ¹ also very particularly preferably represents fluorine,

R ² particularly preferably represents hydrogen,

R ³ particularly preferably represents hydrogen, fluorine, chlorine or methylthio,

R ³ very particularly preferably represents hydrogen,

R ³ also very particularly preferably represents fluorine,

R ⁴ particularly preferably represents hydrogen, methyl or isopropyl,

R ⁴ very particularly preferably represents hydrogen,

R ⁴ also very particularly preferably represents methyl,

R ¹ , R ² , R ³ and R ⁴ very particularly preferably all represent hydrogen,

R ⁵ is preferably hydrogen; C ₁ -C ₆ -alkyl, C ₁ -C ₄ -alkylsulfinyl, C ₁ -C ₄ -alkylsulfonyl, C ₁ -C ₃ -alkoxy-C ₁ -C ₃ -alkyl, C ₃ -C _6- Cycloalkyl; Having 1 to 9 fluorine, chlorine and / or bromine atoms in each case C ₁ -C ₄ - haloalkyl, C ₁ -C ₄ - haloalkylthio, C ₁ -C ₄ - haloalkyl sulfinyl, C ₁ - C ₄ -haloalkylsulfonyl, halo-C ₁ -C ₃ -alkoxy-C ₁ -C ₃ -alkyl or C ₃ -C ₆ -halocycloalkyl; Formyl-C ₁ -C ₃ -alkyl, (C ₁ -C ₃ -alkyl) carbonyl-C ₁ -C ₃ -alkyl, (C ₁ -C ₃ -alkoxy) carbonyl-C ₁ -C ₃ -alkyl ; (C ₁ -C ₃ -haloalkyl) carbonyl-C ₁ -C ₃ -alkyl or (C ₁ -C ₃ -haloalkoxy) carbonyl having 1 to 7 fluorine, chlorine and / or bromine atoms in each case -C ₁ -C ₃ -alkyl; (C ₁ -C ₃ -alkyl) carbonyl-C ₁ -C ₃ -haloalkyl or (C ₁ -C ₃ -alkoxy) carbonyl- having 1 to 6 fluorine, chlorine and / or bromine atoms in each case C ₁ -C ₃ -haloalkyl; (C ₁ -C ₃ -haloalkyl) carbonyl-C ₁ -C ₃ -haloalkyl or (C ₁ -C ₃ -haloalkoxy) carbo having 1 to 13 fluorine, chlorine and / or bromine atoms in each case Nyl-C ₁ -C ₃ -haloalkyl; -COR ⁶ , -CONR ⁷ R ⁸ or -CH ₂ NR ⁹ R ¹⁰ ,

R ⁵ is particularly preferably hydrogen, methyl, ethyl, n- or isopropyl, n-, iso-, sec- or t-butyl, pentyl, hexyl, methylsulfinyl, ethylsulfinyl, n- or isopropylsulphi Nyl, n-, iso-, sec- or t-butylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or isopropylsulfonyl, n-, iso-, sec- or t-butylsulfonyl, methoxy Methyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl, trifluoromethyl, trichloromethyl, trifluoroethyl, difluoromethylthio, difluorochloromethylthio, Trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl, trifluoromethoxymethyl, -CH ₂ -CHO, -CH ₂ CH ₂ -CHO, -CH ₂ -CO-CH ₃ ,- CH ₂ -CO-CH ₂ CH ₃ , -CH ₂ -CO-CH (CH ₃ ) ₂ , -CH ₂ CH ₂ -CO-CH ₃ , -CH ₂ CH ₂ -CO-CH ₂ CH ₃ , -CH ₂ CH ₂ -CO-CH (CH ₃ ) ₂ , -CH ₂ -C (O) OCH ₃ , -CH ₂ -C (O) OCH ₂ CH ₃ , -CH ₂ -C (O) O CH (CH ₃ ) ₂ , -CH ₂ CH ₂ -C (O) OCH ₃ , -CH ₂ CH ₂ -C (O) OCH ₂ CH ₃ , -CH ₂ CH ₂ -C (O) OCH (CH ₃ ) ₂ , -CH ₂ -CO-CF ₃ , -CH ₂ -CO-CCl ₃ , -CH ₂ -CO-CH ₂ CF ₃ , -CH ₂ -CO-CH ₂ CCl ₃ , -CH ₂ CH ₂ -CO- CH ₂ CF ₃ , -CH ₂ CH ₂ -CO-CH ₂ CCl ₃ , -CH ₂ -C (O) OCH ₂ CF ₃ , -CH ₂ -C (O) OCF ₂ CF ₃ , -CH ₂ -C ( O) OCH ₂ CCl ₃ , -CH ₂ -C (O) OCCl ₂ CCl ₃ , -CH ₂ CH ₂ -C (O) OCH ₂ CF ₃ , -CH ₂ CH ₂ -C (O) OCF ₂ CF ₃ , -CH ₂ CH ₂ -C (O) OCH ₂ CCl ₃ , -CH ₂ CH ₂ -C (O) O-CCl ₂ CCl ₃ , -COR ⁶ , -CONR ⁷ R ⁸ or -CH ₂ NR ⁹ R ¹⁰ Indicate,

R ⁵ is very particularly preferably hydrogen, methyl, methoxymethyl, -CH ₂ -CHO, -CH ₂ CH ₂ -CHO, -CH ₂ -CO-CH ₃ , -CH ₂ -CO-CH ₂ CH ₃ , -CH ₂ -CO-CH (CH ₃ ) ₂ or -COR ⁶ ,

R ⁶ is preferably hydrogen, C ₁ -C ₆ -alkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₃ -alkoxy-C ₁ -C ₃ -alkyl, C ₃ -C ₆ -cycloalkyl; C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -haloalkoxy, halo-C ₁ -C ₃ -alkoxy-C ₁ -C ₃ having 1 to 9 fluorine, chlorine and / or bromine atoms in each case -Alkyl or C ₃ -C ₆ -halocycloalkyl, or -COR ¹¹ ;

R ⁶ is particularly preferably hydrogen, methyl, ethyl, n- or iso-propyl, t-butyl, methoxy, ethoxy, isopropoxy, t-butoxy, cyclopropyl, trifluoromethyl, trifluorome Oxy or -COR ¹¹ ;

R ⁶ very particularly preferably represents hydrogen, —COCH ₃ , —CHO, —COCH ₂ OCH ₃ , —COCO ₂ CH ₃ or OCO ₂ CH ₂ CH ₃ ,

R ⁷ and R ⁸ are independently of each other preferably hydrogen, C ₁ -C ₆ -alkyl, C ₁ -C ₃ -alkoxy-C ₁ -C ₃ -alkyl, C ₃ -C ₆ -cycloalkyl; C ₁ -C ₄ -haloalkyl, halo-C ₁ -C ₃ -alkoxy-C ₁ -C ₃ -alkyl or C ₃ -C ₆ -having 1 to 9 fluorine, chlorine and / or bromine atoms in each case Halocycloalkyl, or

R ⁷ and R ⁸ may also contain, together with the nitrogen atom to which they are attached, one or two additional non-adjacent heteroatoms, preferably selected from the group consisting of oxygen, sulfur and NR ¹² , halogen and C ₁ − To form a saturated heterocycle of 5 to 8 reducers, optionally mono- to tetrasubstituted, by the same or different substituents selected from the group consisting of C ₄ -alkyl,

R ⁷ and R ⁸ independently of one another are particularly preferably hydrogen, methyl, ethyl, n- or isopropyl, n-, iso-, sec- or t-butyl, methoxymethyl, methoxyethyl, ethoxymethyl, Ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl, trifluoromethyl, trichloromethyl, trifluoroethyl or trifluoromethoxymethyl, or

R ⁷ and R ⁸ together with the nitrogen atom to which they are attached are particularly preferably mono- to tetrasubstituted morpholine, thiomorpholine and the same or different substituents selected from the group consisting of fluorine, chlorine, bromine and methyl and Forms a saturated heterocycle selected from the group consisting of piperazine, wherein piperazine may be substituted at a second nitrogen atom by R ¹² ,

R ⁹ and R ¹⁰ are independently of each other preferably hydrogen, C ₁ -C ₆ -alkyl, C ₃ -C ₆ -cycloalkyl, or C ₁ -C having 1 to 9 fluorine, chlorine and / or bromine atoms ₄ -haloalkyl or C ₃ -C ₆ -halocycloalkyl, or

R ⁹ and R ¹⁰ may also contain 1 or 2 additional non-adjacent heteroatoms, preferably selected from the group consisting of oxygen, sulfur and NR ¹² , with the nitrogen atom to which they are attached, halogen and C ₁ − To form a saturated heterocycle of 5 to 8 reducers, optionally mono- or polysubstituted, by the same or different substituents selected from the group consisting of C ₄ -alkyl,

R ⁹ and R ¹⁰ independently of one another are particularly preferably hydrogen, methyl, ethyl, n- or isopropyl, n-, iso-, sec- or t-butyl, methoxymethyl, methoxyethyl, ethoxymethyl, Ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl, trifluoromethyl, trichloromethyl, trifluoroethyl or trifluoromethoxymethyl, or

R ⁹ and R ¹⁰ together with the nitrogen atom to which they are attached are particularly preferably mono- to tetrasubstituted morpholine, thiomorpholine and the same or different substituents selected from the group consisting of fluorine, chlorine, bromine and methyl and Forms a saturated heterocycle selected from the group consisting of piperazine, wherein piperazine may be substituted at a second nitrogen atom by R ¹² ,

R ¹¹ is preferably hydrogen, C ₁ -C ₆ -alkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₃ -alkoxy-C ₁ -C ₃ -alkyl, C ₃ -C ₆ -cycloalkyl; C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -haloalkoxy, halo-C ₁ -C ₃ -alkoxy-C ₁ -C ₃ having 1 to 9 fluorine, chlorine and / or bromine atoms in each case -Alkyl or C ₃ -C ₆ -halocycloalkyl;

R ¹¹ is particularly preferably hydrogen, methyl, ethyl, n- or isopropyl, t-butyl, methoxy, ethoxy, isopropoxy, t-butoxy, cyclopropyl, trifluoromethyl or trifluoromethoxy Indicates,

R ¹² preferably represents hydrogen or C ₁ -C ₄ -alkyl,

R ¹² particularly preferably represents hydrogen, methyl, ethyl, n- or isopropyl, or n-, iso-, sec- or t-butyl,

Z preferably represents Z ¹ ,

Z ¹ preferably represents phenyl optionally mono- to substituted by the same or different substituents selected from the W ¹ list,

Z ¹ particularly preferably represents phenyl monosubstituted by a substituent selected from the W ¹ list, or

Z ¹ also particularly preferably represents phenyl disubstituted by the same or different substituents selected from the W ¹ list, or

Z ¹ also particularly preferably represents phenyl trisubstituted by the same or different substituents selected from the W ¹ list,

Z ¹ very particularly preferably represents phenyl mono-substituted by the same or different substituents selected from the W ¹ list, or

Z ¹ very particularly preferably represents phenyl, wherein the 3,4-position is disubstituted by the same or different substituents selected from the W ¹ list, or

Z ¹ very particularly preferably represents phenyl, wherein the 2,4-position is disubstituted by the same or different substituents selected from the W ¹ list, or

Z ¹ very particularly preferably represents phenyl, wherein the 3,5-position is disubstituted by the same or different substituents selected from the W ¹ list, or

Z ¹ very particularly preferably represents phenyl trisubstituted by the same or different substituents at the 2,4,6-positions selected from the W ¹ list,

W ¹ is halogen, cyano, nitro, amino, hydroxyl, formyl, carboxyl, carbamoyl, thiocarbamoyl;

In each case alkyl, hydroxyalkyl, oxoalkyl, alkoxy, alkoxyalkyl, alkylthioalkyl, dialkoxyalkyl, alkylthio, alkylsulfinyl or alkylsulfonyl having from 1 to 8 carbon atoms and in each case straight or branched ;

Alkenyl or alkenyloxy in each case having 2 to 6 carbon atoms and in each case straight or branched chain;

Haloalkyl, haloalkoxy, haloalkyl thio, haloalkylsulfinyl or haloalkylsulfonyl in each case having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms and in each case are straight or branched chains;

Haloalkenyl or haloalkenyloxy in each case having 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms and in each case are straight or branched chains;

Alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl having 1 to 6 carbon atoms in each hydrocarbon chain and in each case are straight or branched chains Arylalkylaminocarbonyl or dialkylaminocarbonyloxy, or alkenylcarbonyl or alkynylcarbonyl having 2 to 6 carbon atoms in each hydrocarbon chain;

In each case cycloalkyl or cycloalkyloxy having 3 to 6 carbon atoms;

Alkylene of 3 or 4 carbon atoms optionally substituted one- to four-substituted and in each case double-bonded by the same or different substituents selected from the group consisting of fluorine, chlorine, oxo, methyl, trifluoromethyl and ethyl, Oxyalkylene having 2 or 3 carbon atoms or dioxyalkylene having 1 or 2 carbon atoms;

Group -C (Q ¹ ) = NQ ²

(From here,

Q ¹ represents hydrogen, hydroxyl, alkyl of 1 to 4 carbon atoms, haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, or cycloalkyl of 1 to 6 carbon atoms,

Q ² represents hydroxyl, amino, methylamino, phenyl or benzyl, or in each case optionally halogen-, cyano-, hydroxyl-, alkoxy-, alkylthio-, alkylamino-, dialkylamino- or phenyl -Substituted alkyl or alkoxy having 1 to 4 carbon atoms, or in each case alkenyloxy or alkynyloxy having 2 to 4 carbon atoms; or

Each cyclic moiety is optionally mono- to trisubstituted by halogen and / or straight or branched chain alkyl or alkoxy having 1 to 4 carbon atoms and in each case phenyl, phenoxy having 1 to 3 carbon atoms in each alkyl moiety; Phenylthio, benzoyl, benzoylethenyl, cinnamoyl, heterocyclyl, phenylalkyl, phenylalkyloxy, phenylalkylthio or heterocyclylalkyl;

W ¹ is preferably fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, sec- or t-butyl, methoxy, ethoxy, n- or i-propoxy, Trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, in each case double-bonded difluoromethylenedioxy or tetrafluoro Ethylenedioxy or group-C (Q ¹ ) = NQ ² ;

From here,

Q ¹ represents hydrogen, methyl, ethyl, trifluoromethyl or cyclopropyl,

Q ² represents hydroxyl, methoxy, ethoxy, propoxy or isopropoxy,

Z also preferably represents Z ² ,

Z ² preferably denotes cycloalkyl or bicycloalkyl, each being optionally mono- to tetrasubstituted by the same or different C ₁ -C ₄ -alkyl and in each case has 3 to 10 carbon atoms,

Z ² particularly preferably represents cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, bicyclo [2.2.1] heptyl or bicyclo [2.2.2] octyl,

Z also preferably represents Z ³ ,

Z ³ preferably represents unsubstituted C ₂ -C ₂₀ -alkyl or is optionally mono-substituted by the same or different substituents selected from the group consisting of fluorine, chlorine, bromine, iodine and C ₃ -C ₆ -cycloalkyl Or polysubstituted C ₁ -C ₂₀ -alkyl, wherein the cycloalkyl moiety is the same selected from the group consisting of fluorine, chlorine, bromine, iodine, C ₁ -C ₄ -alkyl and C ₁ -C ₄ -haloalkyl Or mono- to tetrasubstituted by different substituents,

Z ³ particularly preferably represents unsubstituted C ₂ -C ₂₀ -alkyl,

Z ³ also particularly preferably represents C ₁ -C ₂₀ -alkyl substituted by chlorine, cyclopropyl, dichlorocyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl,

Z also preferably represents Z ⁴ ,

Z ⁴ is preferably C ₂ -C ₂₀ -alkenyl optionally substituted with one or more polysubstituted by the same or different substituents selected from the group consisting of fluorine, chlorine, bromine, iodine and C ₃ -C ₆ -cycloalkyl, respectively; C ₂ -C ₂₀ -alkynyl, wherein the cycloalkyl moiety is the same or different substituent selected from the group consisting of fluorine, chlorine, bromine, iodine, C ₁ -C ₄ -alkyl and C ₁ -C ₄ -haloalkyl May be mono- to tetrasubstituted by

Z ⁴ particularly preferably represents C ₂ -C ₂₀ -alkenyl or C ₂ -C ₂₀ -alkynyl,

Z and R ⁴ also preferably represent, together with the carbon atoms to which they are attached, a 5- or 6-membered carbocyclic or heterocyclic ring which is optionally mono- to tetrasubstituted by the same or different substituents,

Z and R ⁴ also preferably represent a 5- or 6-membered carbocyclic ring which is optionally mono-, di- or trisubstituted by methyl together with the carbon atom to which they are attached.

Preference is furthermore given to compounds of the general formula (Ic):

Where

R ¹ , R ² , R ³ , R ⁴ and Z ¹ are as defined above.

Also preferred are compounds of the general formula (Id):

Where

R ¹ , R ² , R ³ , R ⁴ and Z ² are as defined above.

Preference is furthermore given to compounds of the general formula (Ie):

Where

R ¹ , R ² , R ³ , R ⁴ and Z ³ are as defined above.

Also preferred are compounds of the general formula (If):

Where

R ¹ , R ² , R ³ , R ⁴ and Z ⁴ are as defined above.

Preference is furthermore given to compounds of the general formula (Ib):

Where

R ¹ , R ² , R ³ , R ⁴ and Z ⁴ are as defined above.

Preference is furthermore given to compounds of the general formula (Ig):

Where

R ¹ , R ² , R ³ , R ⁴ , R ^5-1 and Z are as defined above,

R ^5-1 is preferably C ₁ -C ₆ -alkyl, C ₁ -C ₄ -alkylsulfinyl, C ₁ -C ₄ -alkylsulfonyl, C ₁ -C ₃ -alkoxy-C ₁ -C _3- Alkyl, C ₃ -C ₆ -cycloalkyl; Having 1 to 9 fluorine, chlorine and / or bromine atoms in each case C ₁ -C ₄ - haloalkyl, C ₁ -C ₄ - haloalkylthio, C ₁ -C ₄ - haloalkyl sulfinyl, C ₁ - C ₄ -haloalkylsulfonyl, halo-C ₁ -C ₃ -alkoxy-C ₁ -C ₃ -alkyl or C ₃ -C ₆ -halocycloalkyl; Formyl-C ₁ -C ₃ -alkyl, (C ₁ -C ₃ -alkyl) carbonyl-C ₁ -C ₃ -alkyl, (C ₁ -C ₃ -alkoxy) carbonyl-C ₁ -C ₃ -alkyl ; (C ₁ -C ₃ -haloalkyl) carbonyl-C ₁ -C ₃ -alkyl or (C ₁ -C ₃ -haloalkoxy) carbonyl having 1 to 7 fluorine, chlorine and / or bromine atoms in each case -C ₁ -C ₃ -alkyl; (C ₁ -C ₃ -alkyl) carbonyl-C ₁ -C ₃ -haloalkyl or (C ₁ -C ₃ -alkoxy) carbonyl- having 1 to 6 fluorine, chlorine and / or bromine atoms in each case C ₁ -C ₃ -haloalkyl; (C ₁ -C ₃ -haloalkyl) carbonyl-C ₁ -C ₃ -haloalkyl or (C ₁ -C ₃ -haloalkoxy) carbo having 1 to 13 fluorine, chlorine and / or bromine atoms in each case Nyl-C ₁ -C ₃ -haloalkyl; -COR ⁶ , -CONR ⁷ R ⁸ or -CH ₂ NR ⁹ R ¹⁰ ,

R ^5-1 is particularly preferably methyl, ethyl, n- or isopropyl, n-, iso-, sec- or t-butyl, pentyl, hexyl, methylsulfinyl, ethylsulfinyl, n- or isopropylsulphi Nyl, n-, iso-, sec- or t-butylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or isopropylsulfonyl, n-, iso-, sec- or t-butylsulfonyl, methoxy Methyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl, trifluoromethyl, trichloromethyl, trifluoroethyl, difluoromethylthio, difluorochloromethylthio , Trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl, trifluoromethoxymethyl, -CH ₂ -CHO, -CH ₂ CH ₂ -CHO, -CH ₂ -CO-CH ₃ , -CH ₂ -CO-CH ₂ CH ₃ , -CH ₂ -CO-CH (CH ₃ ) ₂ , -CH ₂ CH ₂ -CO-CH ₃ , -CH ₂ CH ₂ -CO-CH ₂ CH ₃ , -CH ₂ CH ₂ -CO-CH (CH ₃ ) ₂ , -CH ₂ -C (O) OCH ₃ , -CH ₂ -C (O) OCH ₂ CH ₃ , -CH ₂ -C (O) OCH (CH ₃ ) ₂ , -CH ₂ CH ₂ -C (O) OCH ₃ , -CH ₂ CH ₂ -C (O) OCH ₂ CH ₃ , -CH ₂ CH ₂ -C (O) OCH (CH ₃ ) ₂ ,- CH ₂ -CO-CF ₃ , -CH ₂ -CO-CCl ₃ , -CH ₂ -CO-CH ₂ CF ₃ , -CH ₂ -CO-CH ₂ CCl ₃ , -CH ₂ CH ₂ -CO-CH ₂ CF ₃ , -CH ₂ CH ₂ -CO-CH ₂ CCl ₃ , -CH ₂ -C (O) OCH ₂ CF ₃ , -CH ₂ -C (O) OCF ₂ CF ₃ , -CH ₂ -C (O) OCH ₂ CCl ₃ , -CH ₂ -C (O) OCCl ₂ CCl ₃ , -CH ₂ CH ₂ -C (O) OCH ₂ CF ₃ , -CH ₂ CH ₂ -C (O) OCF ₂ CF ₃ , -CH ₂ CH ₂ -C (O) OCH ₂ CCl ₃ , -CH ₂ CH ₂ -C (O) O-CCl ₂ CCl ₃ , -COR ⁶ , -CONR ⁷ R ⁸ or -CH ₂ NR ⁹ R ¹⁰ ;

R ^5-1 is very particularly preferably methyl, methoxymethyl, -CH ₂ -CHO, -CH ₂ CH ₂ -CHO, -CH ₂ -CO-CH ₃ , -CH ₂ -CO-CH ₂ CH ₃ , -CH ₂ -CO-CH (CH ₃ ) ₂ or -COR ⁶ .

Saturated or unsaturated hydrocarbon radicals such as alkyl or alkenyl can be as straight or branched as possible in each case, including those bonded to heteroatoms such as for example alkoxy.

Definitions C ₁ -C ₂₀ -alkyl covers the broadest range defined for alkyl radicals. Specifically, this definition is methyl, ethyl, n-, isopropyl, n-, iso-, sec-, t-butyl, in each case all isomers pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodec The meanings of yarn, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl and eicosyl. Among them, methyl, ethyl, n-, isopropyl, n-, iso-, sec-, t-butyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,2-dimethyl Propyl, 2,2-dimethylpropyl, n-hexyl, 1-methylpentyl, 4-methylpentyl, 1,3-dimethylbutyl, 3,3-dimethylbutyl, 1,2,2-trimethylpropyl, n-heptyl, 1-methylhexyl, 5-methylhexyl, 1,4-dimethylpentyl, 4,4-dimethylpentyl, 1,3,3-trimethylbutyl, 1,2,3-trimethylbutyl are preferred.

Definitions C ₂ -C ₂₀ -alkenyl covers the broadest range defined for alkenyl radicals. Specifically, this definition is ethenyl, 1-propenyl, 2-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl -1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-ethylethenyl, and in each case all isomeric pentenyl, hexenyl, heptenyl, octenyl, nonenyl , Decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, nonadecenyl and eicosenyl. Among them, ethenyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1 -Pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 1,2-dimethyl-1-propenyl, 1-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 1, Preference is given to 3-dimethyl-1-butenyl, 1-methyl-1-hexenyl, 1,3,3-trimethyl-1-butenyl.

Definition C ₂ -C ₂₀ -alkynyl covers the broadest range for alkynyl radicals. Specifically, this definition is ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl and in each case all isomeric pentides Neil, hexynyl, heptynyl, octinyl, noninyl, decinyl, undecynyl, dodecynyl, tridecynyl, tetradecynyl, pentadecynyl, hexadecynyl, heptadecynyl, octadecynyl, nona The meanings of decinyl and eicosinyl. Among them, ethynyl, 1-propynyl, 1-butynyl, 3-butynyl, 1-methyl-1-propynyl, 1-pentynyl, 4-pentynyl, 1-hexynyl, 5-hexynyl, Preference is given to 3,3-dimethyl-1-butynyl, 4,4-dimethyl-1-pentynyl, 4,4-dimethyl-2-pentynyl, 1,4-dimethyl-2-pentynyl.

The optionally substituted radical may be mono- or polysubstituted, and when polysubstituted, the substituents may be the same or different.

Halogen-substituted radicals, such as for example haloalkyl, are mono- or polyhalogenated. In the case of polyhalogenated halogen atoms may be the same or different. Here, halogen represents fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine and bromine.

The definition or description of general or preferred radicals given above may be combined between each range and the preferred range as required. The definition applies to both the final product and, correspondingly, to precursors and intermediates.

Explanation of Methods and Intermediates

Method (a)

In case of using 2- (difluoromethyl) benzoyl chloride and 4'-chloro-3'-fluoro-1,1'-biphenyl-2-amine as starting materials, the process (a) according to the invention The process can be represented by the following scheme:

Formula (II) provides a general definition of the difluoromethylbenzoyl derivatives required as starting materials for carrying out process (a) according to the invention. In this general formula (II), X ¹ preferably represents chlorine or hydroxyl.

Difluoromethylbenzoyl derivatives of general formula (II) are known. These are

j) In the first step, 2-formylbenzonitrile of formula (XIV) is fluorinated with (diethylamino) sulfur trifluoride in the presence of a diluent (e.g. methylene chloride),

In the second step, the resulting 2-difluorophenylbenzonitrile of formula (XV) is reacted with a base such as NaOH or KOH [compound of formula (II) wherein X ¹ is hydroxyl],

Optionally in the third step, the acid obtained is reacted with a chlorinating agent (eg thionyl chloride, oxalyl chloride) in the presence of a diluent (eg toluene, methylene chloride) to give the corresponding acid chloride [X ¹ is chlorine; Compound of (II)] is obtained by:

Formula (III) provides a general definition of aniline derivatives which are also necessary as starting materials for carrying out process (a) according to the invention. In this general formula (III), R ¹ , R ² , R ³ , R ⁴ , R ⁵ and Z are preferably, particularly preferably and very particularly preferably the description of compounds of general formula (I) according to the invention. In connection with these radicals each has the meanings mentioned above as preferred, particularly preferred or very particularly preferred.

Most of the starting materials of formula (III) are known and / or can be prepared by known methods (see Bull. Korean Chem. Soc. 2000, 21, 165-166; Chem. Pharm. Bull. 1992, 40 , 240-244; Heterocycles 1989, 29, 1013-1016; J. Med. Chem. 1996, 39, 892-903; Synthesis 1995, 713-16; Synth. Commun. 1994, 24, 267-272; Synthesis 1994, 142-144; DE-A 27 27 416; DE-A 102 190 35; JP-A 9-132567; EP-A 0 824 099; WO 93/11117, EP-A 0 545 099, EP-A 0 589 301 , EP-A 0 589313 and WO 02/38542.

It is also possible to first prepare an aniline derivative of formula (III) wherein R ⁵ represents hydrogen and then derivatize the obtained compound by the above methods using conventional methods [see method (i) according to the invention]. It is possible.

Method (b)

Process according to the invention when using N- (2-bromophenyl) -2- (difluoromethyl) benzamide and 4-chloro-2-fluorophenylboronic acid as starting materials together with a catalyst Can be represented by the following scheme:

Formula (IV) provides a general definition of halodifluoromethylbenzanilides which are necessary as starting materials for carrying out process (b) according to the invention. In this general formula (IV), R ¹ , R ² , R ³ , R ⁴ and R ⁵ are preferably, particularly preferably and very particularly preferably related to the description of the compounds of general formula (I) according to the invention. Thus having the meanings mentioned above as preferred, particularly preferred or very particularly preferred for each of these radicals. X ² represents bromine or iodine.

Halodifluoromethylbenzanilides of formula (IV) are not yet known. These are novel chemical compounds and are also subject to the patent of the present invention. These are

k) difluoromethylbenzoyl derivatives of the general formula (II) are generic in the presence of a catalyst, optionally in the presence of a condenser, optionally in the presence of an acid binder and optionally in the presence of a diluent Obtained by reaction with haloaniline of formula (XVI):

Where

R ¹ , R ² , R ³ , R ⁴ , R ⁵ and X ² are as defined above,

X ¹ represents halogen or hydroxyl.

Method (k)

When using 2- (difluoromethyl) benzoyl chloride and 2-bromoaniline as starting materials, the process of process (i) according to the present invention can be represented by the following scheme:

Difluoromethylbenzoyl derivatives of the general formula (II) which are necessary as starting materials for carrying out process (k) according to the invention have been described above in connection with process (a) according to the invention.

Formula (XVI) provides a general definition of haloaniline which is also needed as starting material for carrying out process (k) according to the invention. In this general formula (XVI), R ¹ , R ² , R ³ , R ⁴ , R ⁵ and X ² are preferably, particularly preferably and very particularly preferably the compounds of general formula (I) according to the invention and With respect to the description of the intermediates of general formula (III) each has the meanings mentioned above as preferred, particularly preferred or very particularly preferred for these radicals.

Haloaniline of formula (XVI) is a known chemical used for synthesis or can be obtained by known methods. If R ⁵ does not represent hydrogen, the radical R ⁵ can be introduced to the compound stage of formula (XVI) using conventional derivatization methods. It is also possible to first prepare a compound of formula (IV) wherein R ⁵ represents hydrogen, and then derivatize the resulting compound in a conventional manner (see method (i) according to the invention).

Formula (V) provides a general definition of boronic acid derivatives which are also necessary as starting materials for carrying out process (b) according to the invention. In this general formula (V), Z ¹ is preferably, particularly preferably and very particularly preferably respectively preferred, particularly preferred or very preferred for Z ¹ with respect to the description of the compounds of the general formula (I) according to the invention. As particularly preferred, they have the meanings mentioned above. A ¹ and A ² each represent hydrogen or together represent tetramethylethylene.

Boronic acid derivatives of formula (V) are known and / or can be prepared by known methods (see, for example, WO 01/90084 and US 5,633,218).

Method (c)

Processes according to the invention when 2-{[2- (difluoromethyl) benzoyl] amino} phenylboronic acid and 1-bromo-4-chloro-3-fluorobenzene as starting material are used together with a catalyst The process of (c) can be represented by the following scheme:

Formula (VI) provides a general definition of the difluoromethylbenzamideboronic acid derivative required as starting material for carrying out process (c) according to the invention. In this general formula (VI), R ¹ , R ² , R ³ , R ⁴ and R ⁵ are preferably, particularly preferably and very particularly preferably related to the description of the compounds of general formula (I) according to the invention. Thus having the meanings mentioned above as preferred, particularly preferred or very particularly preferred for each of these radicals. A ³ and A ⁴ each represent hydrogen or together represent tetramethylethylene.

Difluoromethylbenzamideboronic acid derivatives of formula (VI) are not yet known. These are novel chemical compounds and are also subject to the patent of the present invention. These are

l) difluoromethylbenzoyl derivatives of the general formula (II) in general in the presence of a catalyst, optionally in the presence of a condenser, optionally in the presence of an acid binder and optionally in the presence of a diluent Obtained by reaction with aniline boronic acid derivatives of formula (XVII):

Where

R ¹ , R ² , R ³ , R ⁴ , R ⁵ , A ³ and A ⁴ are as defined above,

X ¹ represents halogen or hydroxyl.

Method (l)

When using 2- (difluoromethyl) benzoyl chloride and 2-aminophenylboronic acid as starting materials, the process of process (l) according to the present invention can be represented by the following scheme:

The difluoromethylbenzoyl derivatives of the general formula (II) necessary as starting materials for carrying out process (l) according to the invention have been described above in connection with process (a) according to the invention.

Formula (XVII) provides a general definition of aniline boronic acid derivatives which are also necessary as starting materials for carrying out process (l) according to the invention. In this general formula (XVII), R ¹ , R ² , R ³ , R ⁴ and R ⁵ are preferably, particularly preferably and very particularly preferably related to the description of the compounds of general formula (I) according to the invention Thus having the meanings mentioned above as preferred, particularly preferred or very particularly preferred for each of these radicals. A ³ and A ⁴ each represent hydrogen or together represent tetramethylethylene.

The aniline boronic acid derivatives of formula (XVII) are known chemicals used for synthesis or can be obtained by known methods. If R ⁵ does not represent hydrogen, the radical R ⁵ can be introduced to the compound stage of formula (XVII) using conventional derivatization methods. It is also possible to first prepare a compound of formula (VI) in which R ⁵ represents hydrogen, and then to derivatize the resulting compound in a conventional manner (see method (i) according to the invention).

Formula (VII) provides a general definition of phenyl derivatives which are also necessary as starting materials for carrying out process (c) according to the invention. In this general formula (VII), Z ¹ is preferably, particularly preferably and very particularly preferably respectively preferred, particularly preferred or very preferred for Z ¹ with respect to the description of the compounds of the general formula (I) according to the invention. As particularly preferred, they have the meanings mentioned above. X ³ represents chlorine, bromine, iodine or trifluoromethylsulfonate.

Phenyl derivatives of formula (VII) are known chemicals used for synthesis.

Method (d)

The starting material, to N - (2- bromophenyl) -2- (difluoromethyl) benzamide and 1-bromo-4-chloro-3-fluoro benzene catalyst and 4,4,4 ', 4' When used with, 5,5,5 ', 5'-octamethyl-2,2'-bis-1,3,2-dioxaborolane, the process of process (d) according to the invention is Can be represented as:

Halodifluoromethylbenzanilides of general formula (IV) and phenyl derivatives of general formula (VII) which are necessary as starting materials for carrying out process (d) according to the invention are prepared according to the processes (b) and (c) In connection with the above description.

4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bis-1,3, which is also needed as starting material for carrying out process (d) according to the invention 2-dioxaborolane is a commercial chemical used for the synthesis.

Method (e)

For example, 2- (difluoromethyl) - N - {2- (1,3- dimethyl-1-butenyl) phenyl} benzamide If the amide is hydrogenated, the process of method (e) according to the invention It can be represented by the following scheme:

Formula (Ia) provides a general definition of difluoromethylbenzanilide which is necessary as a starting material for carrying out process (e) according to the invention. In this general formula (Ia), R ¹ , R ² , R ³ , R ⁴ and R ⁵ are preferably, particularly preferably and very particularly preferably related to the description of the compounds of general formula (I) according to the invention Thus having the meanings mentioned above as preferred, particularly preferred or very particularly preferred for each of these radicals.

Compounds of general formula (Ia) are compounds according to the invention and can be prepared by methods (a), (f), (g) or (h).

Method (f)

For example, if 2- (difluoromethyl) -N- {2- (1-hydroxy-1,3-dimethylbutyl) phenyl] benzamide is dehydrated, the process of process (f) according to the invention Can be represented by the following scheme:

Formula (VIII) provides a general definition of hydroxyalkyldifluoromethylbenzanilides which are necessary as starting materials for carrying out process (f) according to the invention. In this general formula (VIII), R ¹ , R ² , R ³ , R ⁴ and R ⁵ are preferably, particularly preferably and very particularly preferably related to the description of the compounds of general formula (I) according to the invention Thus having the meanings mentioned above as preferred, particularly preferred or very particularly preferred for each of these radicals.

X ⁵ is preferably a fluorine, chlorine, bromine and / or C ₃ -C ₆ - alkyl, hydroxy-cycloalkyl, or optionally the same day by the different substituents selected from the group consisting of - to use a substituted C ₂ - C ₁₂ Wherein the cycloalkyl moiety may be optionally substituted by the same or different substituents selected from the group consisting of halogen and / or C ₁ -C ₄ -alkyl,

X ⁵ is particularly preferably each optionally attached to any position and is each optionally selected from the same or different carriers selected from the group consisting of fluorine, cyclopropyl, difluorocyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl Hydroxyethyl, hydroxypropyl, hydroxybutyl, hydroxypentyl, hydroxyhexyl, hydroxyheptyl, hydroxyoctyl, hydroxynonyl or hydroxydecyl which are, in each case, linear or branched.

Compounds of formula (VIII) are not yet known and are subject to patents as new compounds.

The hydroxyalkyldifluoromethylbenzanilides of formula (VIII) have potent microbial activity and can be used to control unwanted microorganisms in crop protection and material protection.

Hydroxyalkyldifluoromethylbenzanilide of formula (VIII)

m) difluoromethylbenzoyl derivatives of the general formula (II) are generic in the presence of a catalyst, optionally in the presence of a condenser, optionally in the presence of an acid binder and optionally in the presence of a diluent Obtained by reaction with a hydroxyalkylaniline derivative of formula (XVIII):

Where

R ¹ , R ² , R ³ , R ⁴ , R ⁵ and X ⁵ are as defined above,

X ¹ represents halogen or hydroxyl.

Method (m)

For example, when using 2- (difluoromethyl) benzoyl chloride and 2- (2-aminophenyl) -2-pentanol as starting materials, the process of the method (m) according to the present invention is represented by the following scheme. Can be represented:

Difluoromethylbenzoyl derivatives of the general formula (II) which are necessary as starting materials for carrying out process (m) according to the invention have been described above in connection with process (a) according to the invention.

Formula (XVIII) provides a general definition of hydroxyalkylaniline derivatives which are also necessary as starting materials for carrying out process (l) according to the invention. In this general formula (XVIII), R ¹ , R ² , R ³ , R ⁴ , R ⁵ and X ⁵ are preferably, particularly preferably and very particularly preferably the general formulas (I) and (VIII) according to the invention. With respect to the description of the compounds of) each has the meanings mentioned above as preferred, particularly preferred or very particularly preferred for these radicals.

The hydroxyalkylaniline derivatives of formula (XVIII) are known and / or can be obtained by known methods (see eg US 3,917,592 or EP-A 0 824 099). If R ⁵ does not represent hydrogen, the radical R ⁵ can be introduced to the compound stage of formula (XVIII) using conventional derivatization methods. It is also possible to first prepare a compound of the general formula (VIII) in which R ⁵ represents hydrogen, and then to derivatize the resulting compound in a conventional manner (see method (i) according to the invention).

Method (g)

When N- (2-bromophenyl) -2- (difluoromethyl) benzamide and 1-hexine are used as a starting material with a catalyst, the process of the method (g) according to the present invention is represented by the following scheme. Can be broken:

The halodifluoromethylbenzanilides of general formula (IV) which are necessary as starting materials for carrying out process (g) according to the invention have been described above in connection with process (c) according to the invention.

Formula (IX) provides a general definition of alkyne which is also needed as starting material for carrying out process (g) according to the invention.

A ⁵ preferably represents C ₂ -C ₁₀ -alkyl optionally substituted one- to tetrasubstituted by the same or different substituents selected from the group consisting of fluorine, chlorine, bromine and / or C ₃ -C ₆ -cycloalkyl, Wherein the cycloalkyl moiety may be optionally substituted by the same or different substituents selected from the group consisting of halogen and / or C ₁ -C ₄ -alkyl,

A ⁵ is particularly preferably each attached at any position and is optionally selected from the same or different carriers selected from the group consisting of fluorine, cyclopropyl, difluorocyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl, respectively. To tetrasubstituted and in each case straight or branched ethyl, propyl, butyl, pentyl, hexyl, heptyl or octyl.

Alkynes of formula (IX) are known chemicals used for synthesis.

Formula (X) provides a general definition of alkenes which are separately needed as starting materials for carrying out process (g) according to the invention.

A ⁶ , A ⁷ and A ⁸ independently of one another preferably represent hydrogen, each optionally selected from the same or different substituents selected from the group consisting of fluorine, chlorine, bromine and C ₃ -C ₆ -cycloalkyl; Tetrasubstituted alkyl, wherein the cycloalkyl moiety may be optionally substituted by halogen and / or C ₁ -C ₄ -alkyl and the total number of carbon atoms in the open chain portion of the molecule does not exceed 12.

A ⁶ , A ⁷ and A ⁸ independently of one another particularly preferably each represent hydrogen or may each be attached at any position and each is fluorine, cyclopropyl, difluorocyclopropyl, cyclobutyl, cyclopentyl and cyclo And in each case a straight or branched chain, ethyl, propyl, butyl, pentyl, hexyl, heptyl or octyl, optionally mono- to tetrasubstituted by the same or different substituents selected from the group consisting of hexyl, wherein the open chain portion of the molecule Does not exceed 12 carbon atoms.

Alkenes of formula (VII) are known chemicals used for synthesis.

Method (h)

When N- (2-acetylphenyl) -2- (difluoromethyl) benzamide and butyl (triphenyl) phosphonium iodide are used as starting materials, the process of process (h) according to the invention It can be represented by the following scheme:

Formula (XI) provides a general definition of the ketone required as starting material for carrying out process (h) according to the invention. In this general formula (XI), R ¹ , R ² , R ³ , R ⁴ and R ⁵ are preferably, particularly preferably and very particularly preferably related to the description of the compounds of general formula (I) according to the invention. Thus having the meanings mentioned above as preferred, particularly preferred or very particularly preferred for each of these radicals.

A ⁹ preferably represents C ₂ -C ₁₀ -alkyl, optionally mono- to tetrasubstituted by the same or different substituents selected from the group consisting of fluorine, chlorine, bromine and C ₃ -C ₆ -cycloalkyl, wherein The cycloalkyl moiety may be optionally substituted by the same or different substituents selected from the group consisting of halogen and / or C ₁ -C ₄ -alkyl,

A ⁹ is particularly preferably each independently attached to any position and is optionally one selected from the group consisting of fluorine, cyclopropyl, difluorocyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl, optionally selected from the group consisting of -To tetrasubstituted and in each case straight or branched ethyl, propyl, butyl, pentyl, hexyl, heptyl or octyl.

Ketones of formula (VIII) are not yet known. These are novel chemical compounds and are also subject to the patent of the present invention. These are

n) difluoromethylbenzoyl derivatives of the general formula (II) are generic in the presence of a catalyst, optionally in the presence of a condenser, optionally in the presence of an acid binder and optionally in the presence of a diluent Obtained by reaction with ketoaniline of formula (XIX):

Where

R ¹ , R ² , R ³ , R ⁴ , R ⁵ and A ⁹ are as defined above,

X ¹ represents halogen or hydroxyl.

Method (n)

When using 2- (difluoromethyl) benzoyl chloride and 1- (2-aminophenyl) ethanone as starting materials, the process of process (n) according to the present invention can be represented by the following scheme:

Difluoromethylbenzoyl derivatives of the general formula (II) which are necessary as starting materials for carrying out process (n) according to the invention have been described above in connection with process (a) according to the invention.

Formula (XIX) provides a general definition of ketoaniline which is also needed as starting material for carrying out process (n) according to the invention. In this formula (XIX), R ¹ , R ² , R ³ , R ⁴ , R ⁵ and A ⁹ are preferably, particularly preferably and very particularly preferably the general formulas (I) and (XI) according to the invention. With respect to the description of the compounds of) each has the meanings mentioned above as preferred, particularly preferred or very particularly preferred for these radicals.

Ketoaniline of formula (XIX) is known (see, eg, J. Am. Chem. Soc. 1978, 100, 4842-4857 or US 4,032,573) and / or can be obtained by known methods. If R ⁵ does not represent hydrogen, the radical R ⁵ can be introduced to the compound stage of formula (XXII) using conventional derivatization methods. It is also possible to first prepare a compound of the general formula (VIII) in which R ⁵ represents hydrogen, and then to derivatize the resulting compound in a conventional manner (see method (i) according to the invention).

Formula (XII) provides a general definition of phosphorus compounds which are also needed as starting materials for carrying out process (h) according to the invention.

A ¹⁰ preferably represents C ₂ -C ₁₀ -alkyl optionally substituted one- to tetrasubstituted by the same or different substituents selected from the group consisting of fluorine, chlorine, bromine and C ₃ -C ₆ -cycloalkyl, wherein The cycloalkyl moiety may be optionally substituted by halogen and / or C ₁ -C ₄ -alkyl,

A ¹⁰ is particularly preferably each attached at any position and is optionally selected from the same or different carriers selected from the group consisting of fluorine, cyclopropyl, difluorocyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl, respectively. -To tetrasubstituted and in each case straight or branched ethyl, propyl, butyl, pentyl, hexyl, heptyl or octyl,

P _x is preferably a group ^{_{-P + (C 6 H 5)}} 3 Cl -, -P + (C 6 H 5) 3 Br -, -P + (C 6 H 5) 3 I -, -P (= O) (OCH ₃ ) ₃ or -P (= 0) (OC ₂ H ₅ ) ₃ .

Phosphorus compounds of formula (XII) are known and / or may be prepared by known methods (see, eg, Justus Liebigs Ann. Chem. 1953, 580, 44-57 or Pure Appl. Chem. 1964, 9, 307-335).

Method (i)

When N- (4'-chloro-3'-fluoro-1,1'-biphenyl-2-yl) -2- (trifluoromethyl) benzamide and acetyl chloride are used as starting materials, The process of method (i) according to can be represented by the following scheme:

Formula (Ib) provides a general definition of difluoromethylbenzanilide which is necessary as a starting material for carrying out process (i) according to the invention. In this general formula (Ib), R ¹ , R ² , R ³ , R ⁴ and Z are preferably, particularly preferably and very particularly preferably in connection with the description of the compounds of the general formula (I) according to the invention Each of these radicals has the meanings mentioned above as being preferred, particularly preferred or very particularly preferred.

Compounds of formula (Ib) are compounds according to the invention and can be prepared according to processes (a) to (h).

Formula (XIII) provides a general definition of halides which are also needed as starting materials for carrying out process (i) according to the invention. In this general formula (XIII), R ^5-1 is preferably, particularly preferably and very particularly preferably respectively preferred, particularly preferred or very particularly preferred for this radical with respect to the description of the compounds of the general formula (Ig) As having the meanings mentioned above. X ⁶ represents chlorine, bromine or iodine.

Halides of formula (XIII) are known.

Reaction conditions

Suitable diluents for carrying out the processes (a), (k), (l), (m) and (n) according to the invention are all inert organic solvents. These preferably include aliphatic, alicyclic or aromatic hydrocarbons such as 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; Ketones such as acetone, butanone, methyl isobutyl ketone or cyclohexanone; Nitriles such as acetonitrile, propionitrile, n- or isobutyronitrile or benzonitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; Mixtures of these with water or pure water.

The methods (a), (k), (l), (m) and (n) according to the invention are optionally carried out in the presence of a suitable acid acceptor. Suitable acid acceptors are all customary inorganic or organic bases. These preferably include alkaline earth metal or alkali metal hydrides, hydroxides, amides, alkoxides, acetates, carbonates or bicarbonates, for example sodium hydride, sodium amide, lithium diisopropylamide, sodium methoxide, sodium ethoxide Potassium t-butoxide, sodium hydroxide, potassium hydroxide, sodium acetate, sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate or ammonium carbonate, and also tertiary amines such as trimethylamine, triethylamine, tributylamine, N , N-dimethylaniline, N, N-dimethylbenzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene ( DBN) or diazabicycloundecene (DBU).

Processes (a), (k), (l), (m) and (n) according to the invention are optionally carried out in the presence of a suitable condensing agent. Suitable condensing agents are all condensing agents conventionally used for such amidation reactions. Examples thereof include acid halide formers such as phosgene, phosphorus tribromide, phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride or thionyl chloride; Anhydride formers such as ethyl chloroformate, methyl chloroformate, isopropyl chloroformate, isobutyl chloroformate or methanesulfonyl chloride; Carbodiimides such as N, N'-dicyclohexylcarbodiimide (DCC), or other conventional condensing agents such as phosphorus pentoxide, polyphosphoric acid, N, N'-carbonyldiimidazole, 2- Ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ), triphenylphosphine / carbon tetrachloride or bromotripyrrolidinophosphonium hexafluorophosphate may be mentioned.

Processes (a), (k), (l), (m) and (n) according to the invention are optionally carried out in the presence of a catalyst. Examples of these may be mentioned 4-dimethylaminopyridine, 1-hydroxybenzotriazole and dimethylformamide.

When carrying out the processes (a), (k), (l), (m) and (n) according to the invention, the reaction temperature can be varied in a relatively wide range. In general, these processes are carried out at temperatures of 0 to 150 ° C, preferably 0 to 80 ° C.

When carrying out process (a) according to the invention for the preparation of compounds of general formula (I), it is generally from 0.8 to 15 moles, preferably from 0.8 to per mole of difluoromethylbenzoyl derivative of general formula (II) 8 moles of aniline derivatives of general formula (III) are used.

When carrying out process (j) according to the invention for the preparation of compounds of general formula (IV), it is generally from 0.8 to 15 moles, preferably from 0.8 to per mole of difluoromethylbenzoyl derivative of general formula (II) 8 moles of haloaniline of general formula (XIII) are used.

When carrying out process (k) according to the invention for the preparation of compounds of formula (VI), it is generally from 0.8 to 15 moles, preferably from 0.8 to per mole of difluoromethylbenzoyl derivative of formula (II) 8 moles of aniline boronic acid derivatives of the general formula (XIV) are used.

When carrying out process (l) according to the invention for the preparation of compounds of general formula (VIII), it is generally from 0.8 to 15 moles, preferably from 0.8 to per mole of difluoromethylbenzoyl derivative of general formula (II) 8 moles of hydroxyalkylaniline derivatives of the general formula (XV) are used.

When carrying out process (m) according to the invention for the preparation of compounds of general formula (IX), it is generally from 0.8 to 15 moles, preferably from 0.8 to per mole of difluoromethylbenzoyl derivative of general formula (II) 8 moles of ketoaniline of the general formula (XVI) are used.

Suitable diluents for carrying out the processes (b), (c) and (d) according to the invention are all inert organic solvents. These preferably include aliphatic, alicyclic or aromatic hydrocarbons such as 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 isobutyronitrile 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 t-butanol, ethanediol, propane-1,2-diol, ethoxyethanol, methoxyethanol, diethylene Glycol monomethyl ether or diethylene glycol monoethyl ether; Mixtures of these with water or pure water.

When carrying out the processes (b), (c) and (d) according to the invention, the reaction temperature can be varied in a relatively wide range. In general, these processes are carried out at temperatures of 0 to 180 ° C, preferably 20 to 150 ° C.

The methods (b), (c) and (d) according to the invention are optionally carried out in the presence of a suitable acid acceptor. Suitable acid acceptors are all customary inorganic or organic bases. These preferably include alkaline earth metal or alkali metal hydrides, hydroxides, amides, alkoxides, acetates, fluorides, phosphates, carbonates or bicarbonates such as sodium hydride, sodium amide, lithium diisopropylamide, sodium methoxide Side, sodium ethoxide, potassium t-butoxide, sodium hydroxide, potassium hydroxide, sodium acetate, sodium phosphate, potassium phosphate, potassium fluoride, cesium fluoride, sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate or cesium carbonate, and also tertiary Amines such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, N, N-dimethylbenzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N, N- Dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU).

Processes (b), (c) and (d) according to the invention are carried out in the presence of a catalyst, for example a palladium salt or complex. Suitable catalysts are preferably palladium chloride, palladium acetate, tetrakis (triphenylphosphine) palladium, bis (triphenylphosphine) palladium dichloride or 1,1'-bis (diphenylphosphino) ferrocenepalladium (II) Chloride.

Palladium salts and complex ligands such as triethylphosphine, tri-t-butylphosphine, tricyclohexylphosphine, 2- (dicyclohexylphosphine) biphenyl, 2- (di-t-butylphosphine ) Biphenyl, 2- (dicyclohexylphosphine) -2 '-(N, N-dimethylamino) biphenyl, triphenylphosphine, tris- (o-tolyl) phosphine, sodium 3- (diphenylphosph) Pino) benzenesulfonate, tris-2- (methoxyphenyl) phosphine, 2,2'-bis (diphenylphosphine) -1,1'-binafthyl, 1,4-bis (diphenylphosphino ) Butane, 1,2-bis (diphenylphosphine) ethane, 1,4-bis (dicyclohexylphosphine) butane, 1,2-bis (dicyclohexylphosphine) ethane, 2- (dicyclohexyl Phosphine) -2 '-(N, N-dimethylamino) biphenyl, bis (diphenylphosphino) ferrocene or tris- (2,4-t-butylphenyl) phosphite are added separately to the reaction mixture to the reaction mixture It is also possible to produce palladium complexes.

When carrying out process (b) according to the invention for the preparation of compounds of general formula (I), generally 1 to 15 moles, preferably 2 per mole of halodifluoromethylbenzamide of general formula (IV) To 8 moles of boronic acid derivatives of general formula (V) are used.

When carrying out process (c) according to the invention for the preparation of compounds of general formula (I), generally 0.8 to 15 moles, preferably per mole of difluoromethylbenzanilideboronic acid derivative of general formula (VI) 0.8 to 8 moles of phenyl derivatives of the general formula (VII) are used.

When carrying out process (d) according to the invention for the preparation of compounds of general formula (I), it is generally 0.8 to 15 moles, preferably 0.8 per mole of halodifluoromethylbenzanilide of general formula (IV) To 8 moles of phenyl derivative of formula (VII) and 0.8 to 15 moles, preferably 0.8 to 8 moles of 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2 , 2'-bis-1,3,2-dioxaborolane is used.

Suitable diluents for carrying out process (e) according to the invention are all inert organic solvents. These preferably include aliphatic or alicyclic hydrocarbons such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane or decalin; Ethers such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane or 1,2-diethoxyethane; Alcohols such as methanol, ethanol, n- or i-propanol, n-, i-, sec- or t-butanol, ethanediol, propane-1,2-diol, ethoxyethanol, methoxyethanol, diethylene Glycol monomethyl ether or diethylene glycol monoethyl ether, mixtures thereof with water or pure water.

Process (e) according to the invention is carried out in the presence of a catalyst. Suitable catalysts are all catalysts commonly used for hydrogenation. As such, mention may be made of supports, such as Raney nickel, palladium and platinum on activated carbon, as desired.

Instead of using hydrogen with a catalyst, the hydrogenation in process (e) according to the invention can also be carried out in the presence of triethylsilane.

When carrying out process (e) according to the invention, the reaction temperature can be varied in a relatively wide range. In general, this process is carried out at temperatures of 0 to 150 ° C, preferably 20 to 100 ° C.

Process (e) according to the invention is carried out under hydrogen pressure of from 0.5 to 200 bar, preferably from 2 to 50 bar, particularly preferably from 3 to 10 bar.

Suitable diluents for carrying out process (f) according to the invention are all inert organic solvents. These preferably include aliphatic, alicyclic or aromatic hydrocarbons such as 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 an brush; Ketones such as acetone, butanone, methyl isobutyl ketone or cyclohexanone; 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 t-butanol, ethanediol, propane-1,2-diol, ethoxyethanol, methoxyethanol, diethylene Glycol monomethyl ether, diethylene glycol monoethyl ether; Water and mixtures thereof or pure water.

Process (f) according to the invention is optionally carried out in the presence of an acid. Suitable acids are all inorganic and organic protic acids, Lewis acids and also all polymeric acids. These include, for example, hydrogen chloride, sulfuric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, methanesulfonic acid, trifluoromethanesulfonic acid, toluenesulfonic acid, boron trifluoride (also as etherate), boron tribromide, trichloride Aluminum, titanium tetrachloride, tetrabutyl ortho titanate, zinc chloride, iron (III) chloride, antimony pentachloride, acidic ion exchanger, acidic alumina and acidic silica gel.

When carrying out process (f) according to the invention, the reaction temperature can be varied within a relatively wide range. In general, this process is carried out at temperatures of 0 to 150 ° C, preferably 0 to 100 ° C.

Processes (f) and (e) according to the invention can also be carried out in tandem reactions ("single vessel reaction"). To this end, the compound of formula (VIII) is reacted in the presence of a diluent (suitable diluent for method (f)), optionally an acid (suitable acid for method (f)) and triethylsilane, if desired .

Suitable diluents for carrying out process (g) according to the invention are all inert organic solvents. These preferably include nitriles such as acetonitrile, propionitrile, n- or isobutyronitrile or benzonitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide.

Process (g) according to the invention is optionally carried out in the presence of a suitable acid acceptor. Suitable acid acceptors are all customary inorganic or organic bases. These preferably include alkaline earth metal or alkali metal hydrides, hydroxides, amides, alkoxides, acetates, carbonates or bicarbonates, for example sodium hydride, sodium amide, sodium methoxide, sodium ethoxide, potassium t-butoxide , Sodium hydroxide, potassium hydroxide, ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate or ammonium carbonate, and also tertiary amines such as trimethylamine, triethylamine , Tributylamine, N, N-dimethylaniline, N, N-dimethylbenzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO ), Diazabicyclononene (DBN) or diazabicycloundecene (DBU).

Process (g) according to the invention is carried out in the presence of at least one catalyst.

Suitable catalysts are in particular palladium salts or complexes. These are preferably palladium chloride, palladium acetate, tetrakis (triphenylphosphine) palladium or bis (triphenylphosphine) palladium dichloride. It is also possible to add palladium salts and complex ligands separately to the reactants to produce a palladium complex in the reaction mixture.

Suitable ligands are organophosphorus compounds. Examples thereof include triphenylphosphine, tri-o-tolylphosphine, 2,2'-bis (diphenylphosphino) -1,1'-binafyl, dicyclohexylphosphine biphenyl, 1,4- Bis (diphenylphosphino) butane, bisdiphenylphosphinoferrocene, di (t-butylphosphino) biphenyl, di (cyclohexylphosphino) biphenyl, 2-dicyclohexylphosphino-2'-N, N-dimethylaminobiphenyl, tricyclohexylphosphine, tri-t-butylphosphine can be mentioned. However, ligands may not be used.

Process (g) according to the invention is optionally further carried out in the presence of further metal salts, such as copper salts, for example copper (I) iodide.

When carrying out process (g) according to the invention, the reaction temperature can vary within a relatively wide range. In general, this process is carried out at a temperature of 20 to 180 ° C, preferably 50 to 150 ° C.

When carrying out process (g) according to the invention for the preparation of compounds of general formula (I), generally 1 to 5 moles, preferably 1 per mole of halodifluoromethylbenzanilide of general formula (IV) To 2 moles of alkyne of formula (IX) or alkene of formula (X) are used.

Suitable diluents for carrying out process (h) according to the invention are all inert organic solvents. These preferably include aliphatic, alicyclic or aromatic hydrocarbons such as 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 an brush; 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 t-butanol, ethanediol, propane-1,2-diol, ethoxyethanol, methoxyethanol, diethylene Glycol monomethyl ether, diethylene glycol monoethyl ether.

Process (h) according to the invention is optionally carried out in the presence of a suitable acid acceptor. Suitable acid acceptors are all conventional strong bases. These preferably include alkaline earth metal or alkali metal hydrides, hydroxides, amides, alkoxides or alkali metal hydrocarbon compounds such as sodium hydride, sodium hydroxide, potassium hydroxide, sodium amide, lithium diisopropylamide, sodium methoxide , Sodium ethoxide, potassium t-butoxide, methyl lithium, phenyl lithium or butyl lithium.

When carrying out process (h) according to the invention, the reaction temperature can vary within a relatively wide range. In general, this process is carried out at temperatures of -80 to 150 ° C, preferably -30 to 80 ° C.

When carrying out process (h) according to the invention for the preparation of compounds of general formula (I), generally 1 to 5 moles, preferably 1 to 2 moles per mole of ketone of general formula (XI) Phosphorus compounds of (XII) are used.

Suitable diluents for carrying out process (i) according to the invention are all inert organic solvents. These preferably include aliphatic, alicyclic or aromatic hydrocarbons such as 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 hexamethylphosphoric triamide.

Process (i) according to the invention is carried out in the presence of a base. Suitable bases are all customary inorganic or organic bases. These preferably include alkaline earth metal or alkali metal hydrides, hydroxides, amides, alkoxides, acetates, carbonates or bicarbonates, for example sodium hydride, sodium amide, sodium methoxide, sodium ethoxide, potassium t-butoxide , Sodium hydroxide, potassium hydroxide, ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate or cesium carbonate, and also tertiary amines such as trimethylamine, triethylamine , Tributylamine, N, N-dimethylaniline, N, N-dimethylbenzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO) , Diazabicyclononene (DBN) or diazabicycloundecene (DBU).

When carrying out process (i) according to the invention, the reaction temperature can be varied in a relatively wide range. In general, this process is carried out at temperatures of 0 to 150 ° C, preferably 0 to 110 ° C.

When carrying out process (i) according to the invention for the preparation of compounds of general formula (I), generally 0.2 to 5 moles, preferably 0.5 per mole of iodopyrazolylcarboxanilide of general formula (Ib) To 2 moles of a halide of formula (XIII) are used.

All processes according to the invention are generally carried out at atmospheric pressure. However, it is also possible in each case to carry out under elevated or reduced pressure-generally 0.1 to 10 bar.

The substances according to the invention exhibit strong microbicidal activity and can be used to control unwanted microorganisms, for example fungi and bacteria, in crop protection and material protection.

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

Fungicides may be used to remedy the pseudo mono Ada years old child (Pseudomonoadaceae), Li Jovi Asia (Rhizobiaceae), Enterobacter bacteria years old child (Enterobacteriaceae), Corey four bacteria years old child (Corynebacteriaceae) and Streptomyces setae years old child (Streptomycetaceae) in crop protection .

Some examples of pathogens that cause fungal and bacterial diseases of the genus above are mentioned below, but not limited to:

Xanthomonas species, for example Xanthomonas campestris fib . Orissa ( Xanthomonas campestris pv. Oryzae );

Pseudomonas (Pseudomonas) species, such as blood V Pseudomonas when Manly. Lacrymans ( Pseudomonas syringae pv. Lachrymans );

Erwinia species, for example Erwinia amylovora ;

Pythium species, for example Pythium ultimum ;

Phytophthora species, for example Phytophthora infestans ;

Pseudoperonospora species, for example Pseudoperonospora humuli or Pseudoperonospora cubensis ;

Plasmopara species, for example Plasmopara viticola ;

Bremia species, for example Bremia lactucae

Peronospora species, for example Peronospora pisi or Peronospora brassicae ;

Erysiphe species, for example Erysiphe graminis ;

Sphaerotheca species, for example Sphaerotheca fuliginea ;

Podosphaera species, for example Podosphaera leucotricha ;

Venturia species, for example Venturia inaequalis ;

Pyrenophora species, for example Pyrenophora teres or Pyrenophora graminea (conidia form: Drechslera ), isoform: Helmintosporium ( Helminthosporium ));

Cochliobolus species, for example Cochliobolus sativus (conidia form: Dresslera, isoform: Helmintosporium);

Uromyces species, for example Uromyces appendiculatus ;

Puccinia species, for example Puccinia recondita ;

Sclerotinia species, for example Sclerotinia sclerotiorum ;

Tilletia species, for example Tilletia caries ;

Ustilago species, for example Ustilago nuda or Ustilago avenae ;

Pellicularia species, for example Pellicularia sasakii ;

Pyricularia species, for example Pyricularia oryzae ;

Fusarium (Fusarium) species, such as Fusarium cool morum (Fusarium culmorum);

Botrytis species, for example Botrytis cinerea ;

Septoria species, for example Septoria nodorum ;

Leptosphaeria species, for example Leptosphaeria nodorum ;

Cercospora species, for example Cercospora canescens ;

Alternaria species, for example Alternaria brassica and

Pseudocercosporella species, for example Pseudocercosporella herpotrichoides .

The active compounds according to the invention also show very good strengthening action in plants. Thus, they can be used to confer plant protection against attack by unwanted microorganisms.

Here, plant fortifying (resistance-inducing) substances should be understood to mean substances that can stimulate the plant's defense system so that when plants are inoculated with unwanted microorganisms, the plants are given significant resistance to these microorganisms. do.

In this case, unwanted microorganisms should be understood to mean phytopathogenic fungi, bacteria and viruses. Thus, the substances according to the invention can be used to protect plants from invasion by the aforementioned pathogens for a period of time after treatment. The duration of protection after treatment of the plants with the active compounds is generally 1 to 10 days, preferably 1 to 7 days.

Because the plants are tolerable to the active compounds at the concentrations necessary to control plant diseases, it is possible to treat the plant's ground, breeding stems and seeds, and soil.

The active compounds according to the invention are used for the control of cereal diseases, for example Puccinia species, and for the cultivation of grapes and for diseases that appear during fruit and plant growth, for example Botrytis, Venturi or Alternaria species. Especially good results can be obtained.

The active compounds according to the invention can also be used to increase crop yields. In addition, they are low toxicity and exhibit excellent plant compatibility.

The active compounds according to the invention can also be used as herbicides at certain concentrations and application rates, to influence plant growth or to control animal pests. They can also be used as intermediates and precursors for synthesizing other active compounds.

All plants and plant parts can be treated according to the invention. Plant is to be understood here as meaning all plants and plant populations, such as desired or unwanted wild plants or crops (including naturally occurring crops). Crops include plant varieties and transgenic plants that may or may not be protected by the rights of plant breeders, by conventional plant breeding and optimization methods, by biotechnology and recombinant methods, or by these methods It may be a plant obtained by combining. Some of the plants are to be understood as meaning all the above-ground and underground parts and organs of the plant, for example, shoots, leaves, flowers and roots, examples of which are leaves, needles, stalks, stems. ), Flowers, fruits, fruits, seeds, roots, tubers and rhizomes may be mentioned. Some of the plants also include harvesting materials, and nutritional and reproductive materials, such as seedlings, tubers, rhizomes, cuttings and seeds.

Treatment of plants and plant parts with the active compounds according to the invention is also carried out by conventional treatment methods, for example by dipping, spraying, evaporating, spraying, spraying, applying, and in the case of propagating materials, in particular seeds. Or by applying multiple coatings to act directly or on its surroundings, environment or storage space.

The compounds according to the invention can be used to protect the material from being infected and destroyed by unwanted microorganisms.

Industrial materials here are to be understood as meaning non-living materials prepared for industrial use. For example, industrial materials intended to be protected by the active compounds according to the invention from changes or destruction by microorganisms are adhesives, glues, paper, boards, textiles, leather, wood, paints, plastic products, cooling lubricants. And other substances that can be infected or destroyed by microorganisms. Within the scope of the material to be protected, mention may also be made of parts of the production equipment, such as cooling water circuits, which may be damaged by the growth of microorganisms. Industrial materials that may be mentioned within the scope of the present invention are preferably adhesives, glues, paper, cardboard, leather, wood, paints, cooling lubricants and heat transfer fluids, particularly preferably wood.

Microorganisms capable of degrading or changing industrial materials can be mentioned, for example, bacteria, fungi, yeast, algae and slime organisms. The active compounds according to the invention preferably act on fungi, in particular filamentous fungi, wood discoloration and wood destruction fungi (bacsidomycetes) and on modified organisms and algae.

Microorganisms of the following genus may be mentioned by way of example:

Alternaria , for example Alternaria tenuis

Aspergillus , for example Aspergillus niger

Kaeto hate (Chaetomium), for example kaeto hatred Globo breath (Chaetomium globosum),

Coniophora , for example Coniophora puetana ,

Lentinus , for example Lentinus tigrinus ,

Penicillium , for example Penicillium glaucum ,

Polyporus , for example Polyporus versicolor ,

Aureobasidium , for example Aureobasidium pullulans ,

'S nucleoside poma (Sclerophoma), for example, scan nucleoside poma pita EO pillar (Sclerophoma pityophila),

Trichoderma (trichoderma), for example, to irregularities in Trichoderma (Trichoderma viride),

Escherichia , for example Escherichia coli ,

Pseudomonas (Pseudomonas), for example Pseudomonas rugi ah industrial (Pseudomonas aeruginosa) and

Staphylococcus , for example Staphylococcus aureus .

The active compounds may be prepared according to their special physical and / or chemical properties, such as conventional preparations such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols and microcapsules in polymeric and seed coating compositions. Can be converted to ULV cold and warm agents.

These formulations are known methods, for example by mixing the active compounds with extenders, ie liquid solvents, pressurized liquefied gases and / or solid carriers, optionally using surfactants, ie emulsifiers and / or dispersants and / or foam formers. It is manufactured by. If the extender used is water, for example organic solvents can also be used as auxiliary solvents. Suitable liquid solvents are mainly aromatic compounds such as xylene, toluene or alkylnaphthalene; Chlorinated aromatic or chlorinated aliphatic hydrocarbons such as chlorobenzene, chloroethylene or methylene chloride; Aliphatic hydrocarbons such as cyclohexane or paraffins such as petroleum fractions; Alcohols such as butanol or glycols and their ethers and esters; Ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone; Strong polar solvents such as dimethylformamide or dimethylsulfoxide, or water. Liquefied gaseous extenders or carriers refer to liquids that are gaseous at standard temperatures and atmospheric pressures, for example halogenated hydrocarbons and also aerosol propellants such as butane, propane, nitrogen and carbon dioxide. Suitable solid carriers are, for example, ground natural minerals such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as finely divided silica, alumina and silicates. Suitable granular carriers for granules are, for example, pulverized and classified natural rocks such as calcite, marble, pumice, calcite and dolomite, or synthetic granules of inorganic and organic powders, and organic such as sawdust, coconut husks, corn cobs and tobacco stems. Granules of matter. Suitable emulsifiers and / or foam formers are for example nonionic and anionic emulsifiers, for example polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulfonates, alkylsulfates , Arylsulfonates or protein hydrolysates. Suitable dispersants are for example lignosulphite waste liquors and methylcellulose.

Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latex, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or natural and synthetic phospholipids such as cephalin and lecithin Can be. Other possible additives are mineral and vegetable oils.

Colorants such as inorganic pigments such as iron oxide, titanium oxide and prussian blue, and organic pigments such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc; The same micronutrients may be used.

The formulations generally contain 0.1 to 95% by weight, preferably 0.5 to 90% by weight of active compound.

The active compounds according to the invention can also be used on their own or as a mixture with known fungicides, fungicides, acaricides, nematicides or insecticides, for example in order to prevent broadening the activity spectrum or developing resistance in the formulation thereof. May exist. In many cases a synergistic effect is obtained, i.e. the activity of the mixture exceeds the activity of the individual components.

Examples of suitable mixing components include the following compounds:

Fungicides:

2-phenylphenol, 8-hydroxyquinoline sulfate,

Acibenzola-S-methyl, Aldimorph, Amidoflumet, Ampropyl force, Ampropyl force-potassium, Andoprim, Anilazin, Azaconazole, Azoxystrobin,

Benalacyl, Benodanil, Benomyl, Betiavalicab-isopropyl, Benzamacril, Benzamacryl-Isobutyl, Villanaphos, Vinapacryl, Biphenyl, Bittertanol, Blastisidin-S, Bromuco Nazol, buririmate, butiobate, butylamine,

Calcium Polysulfide, Capsaicin, Captapol, Captan, Carbendazim, Carboxin, Caproamide, Carbon, Quinomethionate, Clobenthiazone, Chlorfenazole, Chloroneb, Chlothalonil, Clozolinate, Clozilacon, cyazopamide, cyflufenamide, cymoxanyl, cyproconazole, cyprodinyl, cyprofuram,

Dagger G, devacarb, diclofluanide, diclones, dichlorophene, diclocemet, diclomezin, dichloran, dietofencarb, difenokazole, diflumethorim, dimethirimol, dimetho Morph, Dimoxistrobin, Diconazole, Diconazole-M, Dinocap, Diphenylamine, Dipyrithione, Ditalimphos, Dithianon, Dodine, Drazoxolone,

Edifene Force, Epoxyconazole, Ethaboxam, Ethirimole, Etridazole,

Soxaxadon, phenamidone, phenananil, phenarimol, fenbuconazole, fenfuram, phenhexamide, phenytropan, phenoxanyl, fenpiclonyl, phenpropidine, phenpropimod, ferbam, Fluazinam, Flubenzimin, Fludioxonyl, Flumetober, Flumorph, Fluoromid, Fluoxastrobin, Fluquinconazole, Fluprimidol, Flusilazole, Flusulfamid, Flutolanil , Flutriafol, polpet, pocetyl-Al, pocetyl-sodium, fuberidazole, furalacyl, furametpyr, purcarbanyl, purmecyclolox,

Guazatin,

Hexachlorobenzene, hexaconazole, hymexazole,

Imazalyl, imibenconazole, iminottadine triacetate, iminottadine tris (albesil), iodocarb, ifconazole, ifprobenfos, ifprodione, ifprovalicab, irumamycin, isoprothiolane, iso Ballet,

Kasugamycin, Cresoxime-Methyl,

Mancozeb, maneb, meperimzone, mepanipyrim, mepronil, metallaxyl, metallaxyl-M, metconazole, metasulfocarb, metfuroxam, metiram, metomistrobin, metsulfobox, Mildiomycin, Michael Robutanil, Michael Rozoline,

Natamycin, nicobifen, nitrotal-isopropyl, nobiflumuron, noarimol,

Opuras, orissastrobin, oxadixyl, oxolinic acid, oxpoconazole, oxycarboxycin, oxypentetiin,

Paclobutrazole, pepurazoate, fenconazole, pensicuron, phosphodiphene, phthalide, picoxistrobin, piperaline, polyoxine, polyoxorim, provenazole, prochloraz, procymidone, pro Pamocarb, propanosine-sodium, propiconazole, propineb, proquinazide, prothioconazole, pyraclostrobin, pyrazophos, pyriphenox, pyrimethanyl, pyroquilon, pyroxipur Pyrronitrin,

Quinconazole, quinoxifen, quintogen,

Cymeconazole, spiroxamine, sulfur,

Tebuconazole, Teclophthalam, Tecnazen, Tecyclcyclase, Tetraconazole, Thiabendazole, Tiothiophene, Tifluzamide, Thiophanate-methyl, Thiram, Thioxymide, Tollclofos-methyl , Tolylufluoride, triadimefon, triadimenol, triazbutyl, triazoxide, tricyclamide, tricyclazole, tridemorph, trixystrobin, triflumizol, tripolin, tri Ticonazole,

Uniconazole,

Validamycin A, vinclozoline,

Geneb, Zeram, Joksamid,

(2S) -N- [2- [4-[[3- (4-chlorophenyl) -2-propynyl] oxy] -3-methoxyphenyl] ethyl] -3-methyl-2-[(methylsul Ponyl) amino] butamide,

1- (1-naphthalenyl) -1H-pyrrole-2,5-dione,

2,3,5,6-tetrachloro-4- (methylsulfonyl) pyridine,

2-amino-4-methyl-N-phenyl-5-thiazolecarboxamide,

2-chloro-N- (2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl) -3-pyridinecarboxamide,

3,4,5-trichloro-2,6-pyridinedicarbonitrile,

Actinate,

Cis-1- (4-chlorophenyl) -2- (1H-1,2,4-triazol-1-yl) cycloheptanol,

Methyl 1- (2,3-dihydro-2,2-dimethyl-1H-inden-1-yl) -1H-imidazole-5-carboxylate,

Potassium carbonate,

N- (6-methoxy-3-pyridinyl) cyclopropanecarboxamide,

N-butyl-8- (1,1-dimethylethyl) -1-oxaspiro [4.5] decan-3-amine,

Sodium tetrathiocarbonate, and

Copper salts and preparations, such as Bordeaux mixtures, copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, cupraneb, copper oxide, mancopper, auxin-copper.

disinfectant:

Bronopol, dichlorophene, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octylinone, furancarboxylic acid, oxytetracycline, probenazole, streptomycin, teclophthalam, copper sulfate and other copper agents.

Pesticides / Acaricides / Nematicides:

Abamectin, ABG-9008, Acetate, Acequinosyl, Acetamiprid, Acetoprol, Acrinatrin, AKD-1022, AKD-3059, AKD-3088, Alanicab, Aldicarb, Aldoxicarb, Ale Trin, alletrin 1R-isomer, alpha cipermethrin (alphamethrin), amidoflumet, aminocarb, amitraz, avermectin, AZ 60541, azadirachtin, azamethicose, azinfos-methyl, azine Phosph-ethyl, azocyclotin,

Bacillus pophilia, Bacillus sp. Erytheus, Bacillus subtilis, Bacillus thuringiensis, Bacillus thuringiensis strain EG-2348, Bacillus thuringiensis strain GC-91, Bacillus thuringiensis strain NCTC-11821, baculovirus Seth, Buberia Bassiana, Buberia Tenella, Bendiocarb, Benfuracarb, Bensultap, Benzoxmate, Beta-Cyfluthrin, Beta-Cypermethrin, Bifenazate, Bifenthrin, Vinapacryl , Biooletrin, bioaletrin-S-cyclopentyl-isomer, bioethanomethrin, biopermethrin, bioresmethrin, bistrifluron, BPMC, brofenprox, bromophosph-ethyl, bromopropylate, Brompheninphos (-methyl), BTG-504, BTG-505, bufencarb, buprofezin, butadithiophosphate, butocarboxime, butoxycarboxime, butylpyridaben,

Kadusafos, campechlor, cabaril, cabofuran, cabofennotion, carbosulphan, katop, CGA-50439, quinomethionate, chlordan, chlordimeform, chloretocab, chlorethoxyphosph, chlorfenapyr , Chlorfenbin Force, Chlorfluazuron, Chlormephos, Chlorobenzylate, Chloropicrine, Chlorproxyfen, Chlorpyriphos-methyl, Chlorpyriphos (-ethyl), Clovafortrin, Chromafenozide, Cis-Sai Permethrin, cis-resmethrin, cis-permethrin, clocitrin, cloetocarb, clopentezin, clotianidine, clothiazobene, cordlemon, coomaphos, cyanophenfos, cyanophos, cycloprene, Cyclorotroprin, Cidia Pomonella, Cyfluthrin, Cyhalothrin, Cyhexatin, Cypermethrin, Cyfenotrine (1R-trans isomer), Cyromargin,

DDT, deltamethrin, demethone-S-methyl, demethone-S-methylsulfone, diafenthiuron, dialilifos, diazinone, diclopention, dichlorbos, dicopol, dicrotofoss, dicycla Neil, Diflubenzuron, Dimethoate, Dimethylbinfos, Dinobutone, Dinocap, Dinotefuran, Diophenolran, Disulfotone, Docusat-Sodium, Dofenapain, DOWCO-439,

Eflusilanate, emamectin, emamectin-benzoate, empentrin (1R-isomer), endosulfan, entomorphora species (spp.), EPN, espenvalelate, ethiophencarb, ethiprole, ethione , Etoprophos, etofenprox, ethoxazole, erythropose,

Pampur, Penamifoss, Penazaquine, Penbutatin Oxide, Penfluthrin, Phenythrothione, Phenobucarb, Phenothiocarb, Phenoxa Cream, Phenoxycarb, Penpropartlin, Penpyrad, Penpyri Trine, Phenpyroximate, Pensulfothion, Pention, Pentripanyl, Fenvalrate, Fipronil, Flornicamid, Fluacrypyrim, Fluazuron, Flubenzimin, Flubrositeinate, Flusai Clock-Suron, Flusiteinate, Flufenerim, Flufenoxuron, Flufenprox, Flumethrin, Flupyrazophos, Flutenzin (Flufenzin), Fluvalinate, Phonophos, Formate, Formimoti On, phosphmethyllan, phosphthiazate, fufenfenx (fluxyfen), furathiocarb,

Gamma-HCH, gosiflure, glandlure, granulosis virus,

Halfenprox, halofenozide, HCH, HCN-801, heptenophos, hexaflumuron, hexthiaxose, hydrammonone, hydroprene,

IKA-2002, imidacloprid, imiprotrin, indoxacarb, iodofenfos, iprobenfos, isosafos, isofenfos, isoprocarb, isoxation, ivermectin,

Japonilure,

Cadetrin,

Nuclea polyhedrosis virus, quinoprene,

Lambda cyhalothrin, lindane, lufenuron,

Malathion, mecarbam, mesulfenfos, metaldehyde, metham-sodium, methacryfoss, metamidophos, metharium anisoplier, metharium flavoviride, methidadion, methiocarb, Metomil, Metoprene, Methokcyclo, Methoxyphenozide, Metholcarb, Metoxadiazone, Mevinforce, Milvemectin, Milbemycin, MKI-245, MON-45700, Monoclotophos, Moxidecine, MTI- 800,

Naled, NC-104, NC-170, NC-184, NC-194, NC-196, niclosamide, nicotine, nitenpyram, nithiazine, NNI-0001, NNI-0101, NNI-0250, NNI-9768 , Novaluron, Nobiflumuron,

OK-5101, OK-5201, OK-9601, OK-9602, OK-9701, OK-9802, ometoate, oxamyl, oxydemethone-methyl,

Paesilomyses fumosorusus, parathion-methyl, parathion (-ethyl), permethrin (cis-, trans-), petroleum, PH-6045, phenothrin (1R-trans isomer), pentoate, po Latex, posalon, phosphmet, phosphamidone, phosphocarb, bombard, piperonyl butoxide, pyrimicab, pyrimifos-methyl, pyrimifos-ethyl, praletrin, propenophosphate, promeca Bromo, propaphos, propargite, propeptamphos, propoxur, prothiophos, protoate, protrifenbut, pymetrozine, pyraclophos, pyrethmetrin, pyrethrum, pyridaben, pyridalyl , Pyridapentione, pyridathione, pyrimidipene, pyriproxyfen,

Quinal Force,

Resmethrin, RH-5849, ribavirin, RU-12457, RU-15525,

S-421, S-1833, Salityon, Cebu Force, SI-0009, Silafluorene, Spinosad, Spirodiclofen, Spiromethifene, Sulfluramid, Sulpotep, Sulprophos, SZI-121,

Tau-fluvalinate, tebufenozide, tebufenpyrad, tebupyrimifos, teflubenzuron, tefluthrin, temefos, themibinfos, terbam, terbufoss, tetrachlorbinfos, tetradipon, Tetramethrin, tetramethrin (1R-isomer), tetrasul, theta-cypermethrin, tiacloprid, thiamethoxam, thiapronyl, thiatriphos, thiocylam hydrogen oxalate, thiodicarb, thio Panox, Thiomethone, Thiosulfato-Sodium, Turingiencin, Tolfenpyrad, Tralositerin, Tralomethrin, Transfluthrin, Triarathene, Triamate, Triazophos, Triazonone, Triclofenidine , Trichlorphone, triple lumuron, trimetacarb,

Amidothione, vaniliprole, burbutin, vertisium lecanini,

WL-108477, WL-40027,

YI-5201, YI-5301, YI-5302,

XMC, xylylcarb,

ZA-3274, Zeta-Cypermethrin, Zolapropos, ZXI-8901,

Compound 3-methyl phenyl propylcarbamate (chumaside Z),

Compound 3- (5-chloro-3-pyridinyl) -8- (2,2,2-trifluoroethyl) -8-azabicyclo [3.2.1] octane-3-carbonitrile (CAS Reg. 185982-80-3) and the corresponding 3-endo-isomer (CAS Reg. No. 185984-60-5) (WO-96 / 37494, WO-98 / 25923),

And formulations containing pesticidal active plant extracts, nematodes, fungi or viruses.

It is also possible to admix with other known active ingredients such as herbicides, fertilizers, growth regulators, safeners or signaling substances.

The compounds of the general formula (I) according to the invention in addition also exhibit very good antibacterial activity. These particular skin fungi (dermatophyte) and yeasts, molds and more fungi (e.g. Candida albicans (Candida albicans), Candida glabrata (Candida species (Candida species), such as Candida glabrata)) and epi Dermo python flow kosum ( Epidermophyton floccosum), Aspergillus nigeo (Aspergillus noger) and Aspergillus Fu fumigatus (Aspergillus fumigatus) and tricot python species such as Aspergillus species (Aspergillus species), tricot Python menta him fight (Trichophyton mentagrophyte) (Trichophyton species ), Microsporon canis and Microsporon species such as audouinii ) have a very broad spectrum of antimicrobial action. These fungal lists do not limit the antimicrobial spectrum being covered at all and are for illustrative purposes only.

The active compounds can be used on their own, in the form of their preparations, or in the forms prepared from them, such as ready-to-use solutions, suspensions, hydrating powders, pastes, soluble powders, powders and granules. This applies in conventional manner, for example by spraying, spraying, misting, spraying, spraying, foaming, spraying and the like. In addition, the active compounds may be applied by a microvolume method or the active compound preparation or the active compound itself may be injected into the soil. It is also possible to treat the seeds of the plant.

When the active compounds according to the invention are used as fungicides, the application rate can vary within a relatively wide range depending on the application form. When treating a part of the plant, the application rate of the active compound is generally 0.1 to 10,000 g / dL, preferably 10 to 1,000 g / dL. For seed dressings, the application rate of the active compound is generally from 0.001 to 50 g, preferably from 0.01 to 10 g per kg of seed. When treating the soil, the application rate of the active compound is generally 0.1 to 10,000 g / dL, preferably 1 to 5,000 g / dL.

As mentioned above, all plants and their parts can be treated according to the invention. In a preferred embodiment, wild plant species or plant varieties and plant cultivars obtained by conventional biological breeding methods such as hybrid breeding or protoplast fusion as well as some of these varieties and cultivars are treated. In another preferred embodiment, genetically engineered transgenic plants and plant cultivars (genetically modified organisms) and portions thereof are treated, if appropriate, with conventional methods. The terms "part", "part of the plant" or "plant part" have been described above.

Plants of plant cultivars which are commercially available or used in each case are particularly preferably treated according to the invention. Plant cultivars should be understood as plants having new properties that can be obtained by conventional breeding techniques, mutagenesis or recombinant DNA techniques. These may be cultivar, biotype and genotype.

Depending on the plant species or plant cultivars, their location and growing conditions (soil, climate, growth period, nutrients), an additive (“raising”) effect may also be seen by treatment according to the invention. Thus, for example, reduction in the application rate of substances and compositions which can be used according to the invention and / or broadening the activity spectrum and / or increasing activity, improving plant growth, increasing hot or cold resistance, drought, or water or soil salinity Expected effects such as increased resistance to, increased flowering, increased harvesting, increased maturity, increased crop yields, improved quality and / or nutritional value of harvested products, and improved shelf life and / or treatability of harvested products. It may appear abnormal.

Transformed plants or plant cultivars (ie those obtained by recombinant methods) which are preferably treated according to the invention include all plants which receive genetic material which imparts particularly advantageous useful properties to these plants by recombinant modification treatment. Examples of such properties include improved plant growth, increased high or low temperature resistance, drought, or increased resistance to water or soil salts, increased flowering, ease of harvest, increased maturity, increased crop yields, improved quality of harvested products, and / or Increased nutritional value, and increased shelf life and / or processability of harvested products. Further particular mention of such properties include increased plant defense against animal and microbial pests such as insects, mites, phytopathogenic fungi, bacteria and / or viruses and also increased plant resistance to certain herbicidally active compounds. Examples of transgenic plants include important crop plants, such as cereals (wheat and rice), corn, soybeans, potatoes, cotton, tobacco, oilseed rape and also fruit trees (opening of apples, pears, citrus fruits and grape fruits). Corn, soybeans, potatoes, cotton, tobacco and oilseed rape are particularly emphasized. Highlighted properties are in particular genetic material derived from toxins formed in plants, in particular Bacillus thuringiensis (eg genes CryIA (a), CryIA (b), CryIA (c), CryIIA, CryIIIA, CryIIIB2, Cry9c) Toxins formed on plants (hereinafter referred to as "Bt plants") by Cry2Ab, Cry3Bb and CryIF and combinations thereof increase the plant's defense against insects, arachnids, nematodes, slugs and snails. Also of particular emphasis is the increased defense of plants against fungi, bacteria and viruses due to systemically acquired resistance (SAR), cystemine, phytoalexin, eliminator and resistance genes and correspondingly expressed proteins and toxins. . Another particularly highlighted property is also the increased plant tolerability to certain herbicidally active compounds such as imidazolinone, sulfonylurea, glyphosate or phosphinothricin (eg the "PAT" gene). In each case genes conferring the desired properties of interest can also be present in transgenic plants in mutual combinations. Examples of "Bt plants" include YIELD GARD ^R (e.g. corn, cotton, soybean), KnockOut ^R (e.g. corn), StarLink ^R (e.g. corn), Bollgard ^R (e.g. cotton), Nucotn ^R (e.g. cotton) And corn cultivars, cotton cultivars, soybean cultivars and potato cultivars sold under the NewLeaf ^R (eg potato) tradename. Examples of herbicide-tolerant plants include Roundup Ready ^R (glyphosate tolerant, eg corn, cotton, soybean), Liberty Link ^R (phosphinothricin tolerant, e.g. oilseed rape), IMI ^R (imidazolinone tolerant) And corn cultivars, cotton cultivars, and soybean cultivars, which are commercially available under the STS ^R (sulfonylurea tolerability, such as corn) brand name. Examples of herbicide-tolerant plants (plants bred by conventional methods for herbicide tolerability) may also be mentioned varieties sold under the name Clearfield ^R (eg corn). Of course, the above description also applies to plant cultivars which are plants to be developed and / or marketed in the future, which have the above-mentioned characteristics or which still have the potential to be developed.

The plants listed above can be treated particularly advantageously according to the invention with a compound of the general formula (I) or a mixture of active compounds according to the invention. The preferred ranges mentioned above for the active compounds also apply to the treatment of these plants. Particular emphasis is given to the treatment of plants with the compounds or mixtures specifically mentioned in the present text.

Hereinafter, the preparation and use of the active compounds according to the invention are described by way of examples.

Manufacturing Example

Example 1

150 mg (0.87 mmol) 2-difluoromethylbenzoic acid, 139 mg (0.73 mmol) 2- (1,3,3-trimethylbutyl) phenylamine, 188 mg (1.45 mmol) N, N-diiso Propylethylamine and 508 mg (1.09 mmol) bromotripyrrolidinophosphonium hexafluorophosphate were stirred in 8 ml of acetonitrile for 18 hours at room temperature. To the mixture was added 10 ml of ethyl acetate / water (1: 1) and the organic phase was separated and washed with 10 ml of saturated ammonium chloride solution and then with 10 ml of water. The organic phase was removed and concentrated to dryness to afford 810 mg of crude product. Petroleum ether / ethyl acetate 10: 1 mixture → 250 mg (97.9% of theory) of 2-difluoromethyl-N- [2- (1,3 purified by column chromatography on silica gel 60 using ethyl acetate , 3-trimethylbutyl) phenyl] benzamide [logP (pH 2.3) = 4.38] was obtained.

Similarly to Example 1 and according to the general description of the methods (a) to (i) according to the invention, the compounds of general formula (I) listed in Table 1 below were also obtained.

Table 1

number Z R ⁵ R ⁴ R ³ R ² R ¹ logP One 1,3,3-trimethylbutyl H H H H H 4.38 2 4-chloro-3-fluorophenyl H H H H H 3.67 3 3,4-dichlorophenyl H H H H H 3.96 4 4-chloro-2-methylphenyl H H H H H 4.06 5 1,3-dimethylbutyl H H H H H 4.11 6 4-propoxyiminomethylphenyl H H H H H 4.27 7 4-isopropoxyiminomethylphenyl H H H H H 4.24 8 3-chloro-3-trifluoromethylphenyl H H H H H 3.85

Preparation of Starting Material of Formula (II)

Example (II-1)

Step 1 :

To 45.0 g (343 mmol) of 2-formylbenzonitrile solution in 500 ml dichloromethane, a solution of 47.6 ml of DAST ([diethylamino] sulfur trifluoride) in 50 ml dichloromethane was stirred at room temperature for 2 hours. Dropwise over. The reaction mixture was stirred for 16 hours.

As a workup, the solvent was evaporated and the residue was chromatographed. 29.3 g (56% of theory) of 2-difluoromethylbenzonitrile were obtained as a yellow oil (mass spectrometry: [M + 1] = 154).

Step 2 :

A solution of 29.0 g (189 mmol) of 2-difluoromethylbenzonitrile in 700 ml of 4% aqueous sodium hydroxide solution was heated at reflux for 6 hours. The reaction mixture was cooled to room temperature, poured onto ice and acidified with concentrated hydrochloric acid. The precipitate was filtered off and dried. 19.3 g (58% of theory) of 2-difluoromethylbenzoic acid were obtained in the form of a white solid (mass spectrometry: [M + 1] = 173).

The logP values given were measured according to EEC Directive 79/831 Annex V.A8 by HPLC (high performance liquid chromatography) using a reversed phase column (C 18). Temperature: 43 ° C.

Measurements in acidic range (pH 2.3) were carried out using 0.1% aqueous phosphoric acid and acetonitrile in a linear gradient from 10% acetonitrile to 90% acetonitrile as mobile phase.

The calibration was performed using unbranched alkan-2-ones (3-16 carbon atoms) with known logP values (measured logP values by residence time using linear interpolation between two consecutive alkanones).

UV spectra of 200-400 nm were used to determine the lambda max value as the maximum of the chromatographic signal.

Example of use

Example A

Botrytis Test (Bean) / Protection

Solvent: 24.5 parts by weight of acetone

               24.5 parts by weight of dimethylacetamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

1 part by weight of the active compound is mixed with the solvents and emulsifiers in the amounts mentioned above, and the concentrate is diluted with water to the desired concentration to prepare a suitable formulation of the active compound.

To test for protective activity, young plants were sprayed with the formulation of the active compound at the specified application rate. After drying of the spray coating, two pieces of small agar colonized with Botrytis cinerea were placed on each leaf. Inoculated plants were placed in the dark at about 20 ° C. and 100% relative atmospheric humidity.

Two days after inoculation, the lesion area size on the leaves was evaluated. 0% means efficacy corresponding to the control, and 100% efficacy means no infection was observed.

In this test, for example, the compounds of Preparation Examples 3 and 4 (see Table 1) showed at least 95% efficacy at an application rate of 500 g / ha.

Example B

Pukenia Test (Wheat) / Protection

Solvent: 25 parts by weight of N, N-dimethylacetamide

Emulsifier: 0.6 parts by weight of alkylaryl polyglycol ether

1 part by weight of the active compound is mixed with the solvents and emulsifiers in the amounts mentioned above and the concentrate is diluted with water to the desired concentration to prepare a suitable formulation of the active compound.

To test for protective activity, young plants were sprayed with the active compound preparation at the specified application rate. After spray coating drying, the plants were sprayed with a conidia suspension of Puccinia recondita . The plants were then left for 48 hours in a culture chamber at 20 ° C. and 100% relative atmospheric humidity.

The plants were then placed in a greenhouse at about 20 ° C. and 80% relative atmospheric humidity to facilitate the spread of rust foam.

Evaluation was carried out 10 days after the inoculation. 0% means efficacy corresponding to the control, and 100% efficacy means no infection was observed.

In this test, for example, the compound of Preparation Example 5 (see Table 1) showed 100% efficacy at an application rate of 500 g / ha.

Example C

Spa erotica Test (cucumber) / protection

Solvent: 49 parts by weight of N, N-dimethylacetamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

1 part by weight of the active compound is mixed with the solvents and emulsifiers in the amounts mentioned above, and the concentrate is diluted with water to the desired concentration to prepare a suitable formulation of the active compound.

To test for protective activity, young plants were sprayed with the active compound preparation at the specified application rate. One day after treatment, plants were inoculated with a spore suspension of Sphaerotheca fuliginea . The plants were then placed in a greenhouse at 23 ° C. and 70% relative atmospheric humidity.

Evaluation was carried out 7 days after the inoculation. 0% means efficacy corresponding to the control, and 100% efficacy means no infection was observed.

In this test, for example, the compounds of Preparation Examples 3 and 5 (see Table 1) showed 100% potency at the application rate of 750 g / ha and the compound of Example 4 showed 95% potency.

Claims (10)

Difluoromethylbenzanilide of Formula (I):

Where R ¹ , R ² , R ³ and R ⁴ independently of one another represent hydrogen, fluorine, chlorine, methyl, isopropyl or methylthio, R ⁵ is hydrogen, C ₁ -C ₈ -alkyl, C ₁ -C ₆ -alkylsulfinyl, C ₁ -C ₆ -alkylsulfonyl, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, C ₃ -C ₈ -cycloalkyl; Having 1 to 9 fluorine, chlorine and / or bromine atoms in each case C ₁ -C ₆ - haloalkyl, C ₁ -C ₄ - haloalkylthio, C ₁ -C ₄ - haloalkyl sulfinyl, C ₁ - C ₄ -haloalkylsulfonyl, halo-C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl or C ₃ -C ₈ -halocycloalkyl; Formyl-C ₁ -C ₃ -alkyl, (C ₁ -C ₃ -alkyl) carbonyl-C ₁ -C ₃ -alkyl, (C ₁ -C ₃ -alkoxy) carbonyl-C ₁ -C ₃ -alkyl ; (C ₁ -C ₃ -haloalkyl) carbonyl-C ₁ -C ₃ -alkyl or (C ₁ -C ₃ -haloalkoxy) carbonyl having 1 to 7 fluorine, chlorine and / or bromine atoms in each case -C ₁ -C ₃ -alkyl; Having from 1 to 6 fluorine, chlorine and / or bromine atoms at each occurrence (C ₁ -C ₃ - alkyl) carbonyl -C ₁ -C ₃ - haloalkyl or (C ₁ - C ₃ - alkoxy) carbonyl- C ₁ -C ₃ -haloalkyl; (C ₁ -C ₃ -haloalkyl) carbonyl-C ₁ -C ₃ -haloalkyl or (C ₁ -C ₃ -haloalkoxy) carbo having 1 to 13 fluorine, chlorine and / or bromine atoms in each case Nyl-C ₁ -C ₃ -haloalkyl; -COR ⁶ , -CONR ⁷ R ⁸ or -CH ₂ NR ⁹ R ¹⁰ , R ⁶ is hydrogen, C ₁ -C ₈ -alkyl, C ₁ -C ₈ -alkoxy, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, C ₃ -C ₈ -cycloalkyl; C ₁ -C ₆ -haloalkyl, C ₁ -C ₆ -haloalkoxy, halo-C ₁ -C ₄ -alkoxy-C ₁ -C ₄ with 1 to 9 fluorine, chlorine and / or bromine atoms in each case -Alkyl or C ₃ -C ₈ -halocycloalkyl; Or -COR ¹¹ , R ⁷ and R ⁸ independently of one another are hydrogen, C ₁ -C ₈ -alkyl, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, C ₃ -C ₈ -cycloalkyl; C ₁ -C ₈ -haloalkyl, halo-C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl or C ₃ -C ₈ -having 1 to 9 fluorine, chlorine and / or bromine atoms in each case Halocycloalkyl, or R ⁷ and R ⁸ together with the nitrogen atom to which they are attached may contain one or two additional nonadjacent heteroatoms selected from the group consisting of oxygen, sulfur and NR ¹² , halogen and C ₁ -C ₄ -alkyl To form a saturated heterocycle of 5 to 8 reducers, optionally mono- or polysubstituted, by the same or different substituents selected from the group consisting of R ⁹ and R ¹⁰ are independently of each other hydrogen, C ₁ -C ₈ -alkyl, C ₃ -C ₈ -cycloalkyl; In each case represent C ₁ -C ₈ -haloalkyl or C ₃ -C ₈ -halocycloalkyl having 1 to 9 fluorine, chlorine and / or bromine atoms, R ⁹ and R ¹⁰ together with the nitrogen atom to which they are attached may contain one or two additional nonadjacent heteroatoms selected from the group consisting of oxygen, sulfur and NR ¹² , halogen and C ₁ -C ₄ -alkyl To form a saturated heterocycle of 5 to 8 reducers optionally mono- or polysubstituted by the same or different substituents selected from the group consisting of R ¹¹ is hydrogen, C ₁ -C ₈ -alkyl, C ₁ -C ₈ -alkoxy, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, C ₃ -C ₈ -cycloalkyl; C ₁ -C ₆ -haloalkyl, C ₁ -C ₆ -haloalkoxy, halo-C ₁ -C ₄ -alkoxy-C ₁ -C ₄ with 1 to 9 fluorine, chlorine and / or bromine atoms in each case -Alkyl or C ₃ -C ₈ -halocycloalkyl; R ¹² represents hydrogen or C ₁ -C ₆ -alkyl, Z represents Z ¹ , Z ² , Z ³ or Z ⁴ , From here, Z ¹ represents phenyl optionally mono- to substituted by the same or different substituents, Z ² represents a bicycloalkyl or cycloalkyl optionally mono- or polysubstituted by the same or different substituents, Z ³ is unsubstituted C ₂ -C ₂₀ ring - represents an alkyl or halogen and C ₃ -C ₆ - cycloalkyl optionally substituted by identical or different substituents selected from the group consisting of alkyl mono- or multi-substituted C ₁ -C ₂₀ -Alkyl, wherein the cycloalkyl moiety can be optionally mono- or polysubstituted by the same or different substituents selected from the group consisting of halogen and C ₁ -C ₄ -alkyl, Z ⁴ represents C ₂ -C ₂₀ -alkenyl or C ₂ -C ₂₀ -alkynyl, optionally mono- or polysubstituted by the same or different substituents selected from the group consisting of halogen and C ₃ -C ₆ -cycloalkyl, respectively Wherein the cycloalkyl moiety may be optionally mono- or polysubstituted by the same or different substituents selected from the group consisting of halogen and C ₁ -C ₄ -alkyl, R ¹ , R ² and R ³ independently of one another represent hydrogen or fluorine, Z and R ⁴ together with the carbon atom to which they are attached form an optionally substituted 5- or 6-membered carbocyclic or heterocyclic ring. The method of claim 1, R ¹ , R ² , R ³ and R ⁴ independently of one another represent hydrogen, fluorine, chlorine or methyl, R ⁵ is hydrogen; C ₁ -C ₆ -alkyl, C ₁ -C ₄ -alkylsulfinyl, C ₁ -C ₄ -alkylsulfonyl, C ₁ -C ₃ -alkoxy-C ₁ -C ₃ -alkyl, C ₃ -C _6- Cycloalkyl; Having 1 to 9 fluorine, chlorine and / or bromine atoms in each case C ₁ -C ₄ - haloalkyl, C ₁ -C ₄ - haloalkylthio, C ₁ -C ₄ - haloalkyl sulfinyl, C ₁ - C ₄ -haloalkylsulfonyl, halo-C ₁ -C ₃ -alkoxy-C ₁ -C ₃ -alkyl or C ₃ -C ₆ -halocycloalkyl; Formyl-C ₁ -C ₃ -alkyl, (C ₁ -C ₃ -alkyl) carbonyl-C ₁ -C ₃ -alkyl, (C ₁ -C ₃ -alkoxy) carbonyl-C ₁ -C ₃ -alkyl ; (C ₁ -C ₃ -haloalkyl) carbonyl-C ₁ -C ₃ -alkyl or (C ₁ -C ₃ -haloalkoxy) carbonyl having 1 to 7 fluorine, chlorine and / or bromine atoms in each case -C ₁ -C ₃ -alkyl; (C ₁ -C ₃ -alkyl) carbonyl-C ₁ -C ₃ -haloalkyl or (C ₁ -C ₃ -alkoxy) carbonyl- having 1 to 6 fluorine, chlorine and / or bromine atoms in each case C ₁ -C ₃ -haloalkyl; (C ₁ -C ₃ -haloalkyl) carbonyl-C ₁ -C ₃ -haloalkyl or (C ₁ -C ₃ -haloalkoxy) carbo having 1 to 13 fluorine, chlorine and / or bromine atoms in each case Nyl-C ₁ -C ₃ -haloalkyl; -COR ⁶ , -CONR ⁷ R ⁸ or -CH ₂ NR ⁹ R ¹⁰ , R ⁶ is hydrogen, C ₁ -C ₆ -alkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₃ -alkoxy-C ₁ -C ₃ -alkyl, C ₃ -C ₆ -cycloalkyl; C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -haloalkoxy, halo-C ₁ -C ₃ -alkoxy-C ₁ -C ₃ having 1 to 9 fluorine, chlorine and / or bromine atoms in each case -Alkyl or C ₃ -C ₆ -halocycloalkyl, or -COR ¹¹ ; R ⁷ and R ⁸ independently of one another are hydrogen, C ₁ -C ₆ -alkyl, C ₁ -C ₃ -alkoxy-C ₁ -C ₃ -alkyl, C ₃ -C ₆ -cycloalkyl; C ₁ -C ₄ -haloalkyl, halo-C ₁ -C ₃ -alkoxy-C ₁ -C ₃ -alkyl or C ₃ -C ₆ -having 1 to 9 fluorine, chlorine and / or bromine atoms in each case Halocycloalkyl, R ⁹ and R ¹⁰ are independently of each other hydrogen, C ₁ -C ₆ -alkyl, C ₃ -C ₆ -cycloalkyl, or C ₁ -C ₄ -halo having 1 to 9 fluorine, chlorine and / or bromine atoms Alkyl or C ₃ -C ₆ -halocycloalkyl, R ¹¹ is hydrogen, C ₁ -C ₆ -alkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₃ -alkoxy-C ₁ -C ₃ -alkyl, C ₃ -C ₆ -cycloalkyl; C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -haloalkoxy, halo-C ₁ -C ₃ -alkoxy-C ₁ -C ₃ having 1 to 9 fluorine, chlorine and / or bromine atoms in each case -Alkyl or C ₃ -C ₆ -halocycloalkyl; R ¹² represents hydrogen or C ₁ -C ₄ -alkyl, Z represents Z ¹ , Z ² , Z ³ or Z ⁴ , Z ¹ represents phenyl optionally mono- to substituted by the same or different substituents selected from the W ¹ list, W ¹ is halogen, cyano, nitro, amino, hydroxyl, formyl, carboxyl, carbamoyl, thiocarbamoyl; In each case alkyl, hydroxyalkyl, oxoalkyl, alkoxy, alkoxyalkyl, alkylthioalkyl, dialkoxyalkyl, alkylthio, alkylsulfinyl or alkylsulfonyl having from 1 to 8 carbon atoms and in each case straight or branched ; Alkenyl or alkenyloxy in each case having 2 to 6 carbon atoms and in each case straight or branched chain; Haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl in each case having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms and in each case are straight or branched chains; Haloalkenyl or haloalkenyloxy in each case having 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms and in each case are straight or branched chains; Alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbons having from 1 to 6 carbon atoms in each hydrocarbon chain and in each case are straight or branched chains; Aryl, arylalkylaminocarbonyl or dialkylaminocarbonyloxy, or alkenylcarbonyl or alkynylcarbonyl having 2 to 6 carbon atoms in each hydrocarbon chain; In each case cycloalkyl or cycloalkyloxy having 3 to 6 carbon atoms; Alkylene of 3 or 4 carbon atoms optionally substituted one- to four-substituted and in each case double-bonded by the same or different substituents selected from the group consisting of fluorine, chlorine, oxo, methyl, trifluoromethyl and ethyl, Oxyalkylene having 2 or 3 carbon atoms or dioxyalkylene having 1 or 2 carbon atoms; Group -C (Q ¹ ) = NQ ² (From here, Q ¹ represents hydrogen, hydroxyl, alkyl of 1 to 4 carbon atoms, haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, or cycloalkyl of 1 to 6 carbon atoms, Q ² represents hydroxyl, amino, methylamino, phenyl or benzyl, or in each case optionally halogen-, cyano-, hydroxyl-, alkoxy-, alkylthio-, alkylamino-, dialkylamino- or phenyl -Substituted alkyl or alkoxy having 1 to 4 carbon atoms, or in each case alkenyloxy or alkynyloxy having 2 to 4 carbon atoms; or Each cyclic moiety is optionally mono- to trisubstituted by halogen and / or straight or branched chain alkyl or alkoxy having 1 to 4 carbon atoms and in each case phenyl, phenoxy having 1 to 3 carbon atoms in each alkyl moiety; Phenylthio, benzoyl, benzoylethenyl, cinnamoyl, heterocyclyl, phenylalkyl, phenylalkyloxy, phenylalkylthio or heterocyclylalkyl; Z ² represents cycloalkyl or bicycloalkyl, each optionally being _1- to tetrasubstituted by the same or different C ₁ -C ₄ -alkyl, in each case having 3 to 10 carbon atoms, Z ³ represents unsubstituted C ₂ -C ₂₀ -alkyl or is optionally mono- or polysubstituted by the same or different substituents selected from the group consisting of fluorine, chlorine, bromine, iodine and C ₃ -C ₆ -cycloalkyl C ₁ -C ₂₀ -alkyl wherein the cycloalkyl moiety is the same or different substituent selected from the group consisting of fluorine, chlorine, bromine, iodine, C ₁ -C ₄ -alkyl and C ₁ -C ₄ -haloalkyl May be mono- to tetrasubstituted by Z ⁴ is C ₂ -C ₂₀ -alkenyl or C ₂ -optionally mono- or polysubstituted by the same or different substituents selected from the group consisting of fluorine, chlorine, bromine, iodine and C ₃ -C ₆ -cycloalkyl, respectively C ₂₀ -alkynyl, wherein the cycloalkyl moiety is selected from the same or different substituents selected from the group consisting of fluorine, chlorine, bromine, iodine, C ₁ -C ₄ -alkyl and C ₁ -C ₄ -haloalkyl -To tetrasubstituted, Z and R ⁴ together with the carbon atoms to which they are attached represent a 5- or 6-membered carbocyclic or heterocyclic ring optionally substituted with one or four to four substituents by the same or different substituents; Fluoromethylbenzanilide. a) General difluoromethylbenzoyl derivatives of the general formula (II) are optionally present in the presence of a catalyst, optionally in the presence of a condensing agent, optionally in the presence of an acid binder and optionally in the presence of a diluent Reacted with the aniline derivative of formula (III), or b) reacting the halodifluoromethylbenzanilide of formula (IV) with the boronic acid derivative of formula (V) in the presence of a catalyst, optionally in the presence of an acid binder and optionally in the presence of a diluent , c) reacting the difluoromethylbenzamide boronic acid derivative of general formula (VI) with a phenyl derivative of general formula (VII) in the presence of a catalyst, optionally in the presence of an acid binder and optionally in the presence of a diluent Or d) halodifluoromethylbenzanilide of general formula (IV) in the presence of palladium or nickel catalyst, 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2 Reacting with a phenyl derivative of formula (VII) in the presence of a '-bis-1,3,2-dioxaborolane, optionally in the presence of an acid binder and optionally in the presence of a diluent, e) hydrogenating difluoromethylbenzanilide of general formula (Ia), optionally in the presence of a diluent and optionally in the presence of a catalyst, or f) dehydrating hydroxyalkyldifluoromethylbenzanilide of general formula (VIII), optionally in the presence of a diluent and optionally in the presence of an acid, g) Halogen-difluoromethylbenzanilides of general formula (IV) are optionally substituted with general formula (IX) in the presence of a diluent, optionally in the presence of an acid binder and optionally in the presence of at least one catalyst Reacted with an alkyne or an alkene of formula (X), or h) reacting a ketone of general formula (XI) with a phosphorus compound of general formula (XII), optionally in the presence of a diluent, i) reacting the difluoromethylbenzanilide of general formula (Ib) with a halide of general formula (XIII) in the presence of a base and in the presence of a diluent, Process for preparing difluoromethylbenzanilide:

Where R ¹ , R ² , R ³ , R ⁴ , R ⁵ , Z, Z ¹ , R ⁶ , R ⁷ , R ⁸ , R ⁹ and R ¹⁰ are as defined in claim 1, X ¹ represents chlorine or hydroxyl, X ² represents chlorine, bromine, iodine or trifluoromethylsulfonate, A ¹ and A ² each represent hydrogen or together represent tetramethylethylene, A ³ and A ⁴ each represent hydrogen or together represent tetramethylethylene, X ³ represents chlorine, bromine, iodine or trifluoromethylsulfonate, X ⁴ represents C ₂ -C ₂₀ -alkenyl or C ₂ -C ₂₀ -alkynyl, optionally mono- or polysubstituted by the same or different substituents selected from the group consisting of halogen and C ₃ -C ₆ -cycloalkyl, respectively Wherein the cycloalkyl moiety may be optionally substituted by halogen and / or C ₁ -C ₄ -alkyl, X ⁵ represents C ₂ -C ₂₀ -hydroxyalkyl optionally mono- or polysubstituted by the same or different substituents selected from the group consisting of halogen and C ₃ -C ₆ -cycloalkyl, wherein the cycloalkyl moiety is halogen And / or optionally substituted by C ₁ -C ₄ -alkyl, A ⁵ represents C ₂ -C ₁₈ -alkyl optionally mono- or polysubstituted by the same or different substituents selected from the group consisting of halogen and C ₃ -C ₆ -cycloalkyl, wherein the cycloalkyl moiety is halogen and // Or optionally substituted by C ₁ -C ₄ -alkyl, A ⁶ , A ⁷ and A ⁸ each independently represent hydrogen, or are optionally mono- or polysubstituted by the same or different substituents selected from the group consisting of halogen and C ₃ -C ₆ -cycloalkyl, and the open chain of the molecule Alkyl of the moiety not exceeding 20, wherein the cycloalkyl moiety may be optionally substituted by halogen and / or C ₁ -C ₄ -alkyl, A ⁹ represents hydrogen or C ₁ -C ₁₈ -alkyl optionally mono- or polysubstituted by the same or different substituents selected from the group consisting of halogen and C ₃ -C ₆ -cycloalkyl, wherein cycloalkyl Moieties may be optionally substituted by halogen and / or C ₁ -C ₄ -alkyl, A ¹⁰ represents C ₁ -C ₁₈ -alkyl optionally mono- or polysubstituted by the same or different substituents selected from the group consisting of halogen and C ₃ -C ₆ -cycloalkyl, wherein the cycloalkyl moiety is halogen and // Or optionally substituted by C ₁ -C ₄ -alkyl, P _x is a group _{^{-P + (C 6 H 5)}} 3 Cl -, -P + (C 6 H 5) 3 Br -, -P + (C 6 H 5) 3 I -, -P (= O) ( OCH ₃ ) ₃ or -P (= O) (OC ₂ H ₅ ) ₃ , R ^5-1 is C ₁ -C ₈ -alkyl, C ₁ -C ₆ -alkylsulfinyl, C ₁ -C ₆ -alkylsulfonyl, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, C ₃ -C ₈ -cycloalkyl; Having 1 to 9 fluorine, chlorine and / or bromine atoms in each case C ₁ -C ₆ - haloalkyl, C ₁ -C ₄ - haloalkylthio, C ₁ -C ₄ - haloalkyl sulfinyl, C ₁ - C ₄ -haloalkylsulfonyl, halo-C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl or C ₃ -C ₈ -halocycloalkyl; Formyl-C ₁ -C ₃ -alkyl, (C ₁ -C ₃ -alkyl) carbonyl-C ₁ -C ₃ -alkyl, (C ₁ -C ₃ -alkoxy) carbonyl-C ₁ -C ₃ -alkyl ; (C ₁ -C ₃ -haloalkyl) carbonyl-C ₁ -C ₃ -alkyl or (C ₁ -C ₃ -haloalkoxy) carbonyl having 1 to 7 fluorine, chlorine and / or bromine atoms in each case -C ₁ -C ₃ -alkyl; (C ₁ -C ₃ -alkyl) carbonyl-C ₁ -C ₃ -haloalkyl or (C ₁ -C ₃ -alkoxy) carbonyl- having 1 to 6 fluorine, chlorine and / or bromine atoms in each case C ₁ -C ₃ -haloalkyl; (C ₁ -C ₃ -haloalkyl) carbonyl-C ₁ -C ₃ -haloalkyl or (C ₁ -C ₃ -haloalkoxy) carbo having 1 to 13 fluorine, chlorine and / or bromine atoms in each case Nyl-C ₁ -C ₃ -haloalkyl; -COR ⁶ , -CONR ⁷ R ⁸ or -CH ₂ NR ⁹ R ¹⁰ , X ⁶ represents chlorine, bromine or iodine. A composition for the control of unwanted microorganisms, characterized in that it contains at least one difluoromethylbenzanilide of formula (I) according to claim 1 together with an extender and / or a surfactant. Use of difluoromethylbenzanilide of formula (I) according to claim 1 for controlling unwanted microorganisms. A method for controlling unwanted microorganisms, characterized in that the difluoromethylbenzanilide of formula (I) according to claim 1 is applied to microorganisms and / or their habitats. A process for preparing an unwanted microbial composition, characterized in that the difluoromethylbenzanilide of formula (I) according to claim 1 is mixed with an extender and / or a surfactant. Hydroxyalkyllodifluoromethylbenzanilides of formula (VIII):

Where R ¹ , R ² , R ³ , R ⁴ and R ⁵ are as defined in claim 1, X ⁵ represents C ₂ -C ₂₀ -hydroxyalkyl optionally mono- or polysubstituted by the same or different substituents selected from the group consisting of halogen and C ₃ -C ₆ -cycloalkyl, wherein the cycloalkyl moiety is halogen And / or C ₁ -C ₄ -alkyl. Difluoromethylbenzoyl Derivatives of Formula (II):

Where X ¹ represents chlorine or hydroxyl. In the first step, 2-formylbenzonitrile of formula (XIV) is fluorinated with (diethylamino) sulfur trifluoride in the presence of a diluent, In the second step, the resulting 2-difluorophenylbenzonitrile of formula (XV) is reacted with a base, Optionally in a third step, the obtained acid is reacted with a chlorinating agent in the presence of a diluent to give the corresponding acid chloride to prepare a difluoromethylbenzoyl derivative of formula (II) according to claim 9 How to: