DE10360369A1 - amides - Google Patents

Abstract

Amides of the formula (I), DOLLAR F1 in which the symbols have the meanings given in the description, a process for the preparation of these substances and their use for controlling undesired microorganisms DOLLAR A and intermediates of the formulas (IIIa) and (IIIb), DOLLAR F2 where the symbols have the meanings given in the description.

Description

The Invention relates to amides, several processes for their preparation and their use to combat from harmful Organisms.

It has already been disclosed that certain amides which are constitutionally similar to the compounds described below have fungicidal properties (cf., for example, US Pat. JP 2001348378 ). However, the fungicidal action of these compounds leaves room for improvement in some cases.

in welcher
R¹, R², und R³ gleich oder verschieden sind und unabhängig voneinander für Wasserstoff, Halogen, Cyano, Nitro,
jeweils geradkettiges oder verzweigtes Alkyl, Alkoxy, Alkylthio, Alkylsulfinyl oder Alkylsulfonyl mit jeweils 1 bis 8 Kohlenstoffatomen;
jeweils geradkettiges oder verzweigtes Alkenyl, Alkinyl, Alkenyloxy oder Alkinyloxy mit jeweils 2 bis 6 Kohlenstoffatomen;
jeweils geradkettiges oder verzweigtes Halogenalkyl, Halogenalkoxy, Halogenalkylthio, Halogenalkylsulfinyl oder Halogenalkylsulfonyl mit jeweils 1 bis 6 Kohlenstoffatomen und 1 bis 13 gleichen oder verschiedenen Halogenatomen;
jeweils geradkettiges oder verzweigtes Halogenalkenyl oder Halogenalkenyloxy mit jeweils 2 bis 6 Kohlenstoffatomen und 1 bis 13 gleichen oder verschiedenen Halogenatomen;
jeweils geradkettiges oder verzweigtes Alkylamino, Dialkylamino, Alkylcarbonyl, Alkoxycarbonyl, Hydroximinoalkyl oder Alkoximinoalkyl mit jeweils 1 bis 6 Kohlenstoffatomen in den einzelnen Alkylteilen;
Cycloalkyl mit 3 bis 6 Kohlenstoffatomen stehen,
wobei
R¹, R², und R³ nicht gleichzeitig für Wasserstoff stehen, oder
R¹ und R² gemeinsam mit den Kohlenstoffatomen, an die sie gebunden sind, einen carbocyclischen Ring bilden,
Het für einen unsubstituierten oder substituierten fünfgliedrigen aromatischen heterocyclischen Ring steht,
R⁴ für Wasserstoff, Halogen, Cyano, Alkyl mit 1 bis 8 Kohlenstoffatomen, Alkenyl oder Alkinyl mit 2 bis 8 Kohlenstoffatomen oder Halogenalkyl mit 1 bis 8 Kohlenstoffatomen und 1 bis 9 Halogenatomen steht,
R⁵ und R⁶ gleich oder verschieden sind und unabhängig voneinander für unsubstituiertes oder jeweils durch Halogen oder Cyano substituiertes Alkyl, Alkoxyalkyl mit jeweils 1–8 Kohlenstoffatomen in den jeweiligen Alkylketten oder Alkenyl oder Alkinyl mit jeweils 2–8 Kohlenstoffatomen oder Cycloalkyl mit 3–8 Kohlenstoffatomen oder für unsubstituiertes oder substituiertes Arylalkyl mit 1–8 Kohlenstoffatomen in der Alkylkette steht,
A für Alkandiyl oder Cycloalkandiyl steht und
Y für Sauerstoff oder Schwefel steht.New compounds of the general formula (I) were found,

in which
R ¹ , R ² , and R ^{3 are the} same or different and are independently hydrogen, halogen, cyano, nitro,
in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl having in each case 1 to 8 carbon atoms;
in each case straight-chain or branched alkenyl, alkynyl, alkenyloxy or alkynyloxy having in each case 2 to 6 carbon atoms;
in each case straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
in each case straight-chain or branched haloalkenyl or haloalkenyloxy having in each case 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
in each case straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, hydroximinoalkyl or alkoximinoalkyl having in each case 1 to 6 carbon atoms in the individual alkyl moieties;
Cycloalkyl of 3 to 6 carbon atoms,
in which
R ¹ , R ² , and R ^{3 are} not simultaneously hydrogen, or
R ¹ and R ² together with the carbon atoms to which they are attached form a carbocyclic ring,
Het is an unsubstituted or substituted five-membered aromatic heterocyclic ring,
R ^{4 is} hydrogen, halogen, cyano, alkyl of 1 to 8 carbon atoms, alkenyl or alkynyl of 2 to 8 carbon atoms or haloalkyl of 1 to 8 carbon atoms and 1 to 9 halogen atoms,
R ⁵ and R ^{6 are the} same or different and are each independently unsubstituted or substituted by halogen or cyano alkyl, alkoxyalkyl each having 1-8 carbon atoms in the respective alkyl chains or alkenyl or alkynyl each having 2-8 carbon atoms or cycloalkyl 3-8 Is carbon atoms or unsubstituted or substituted arylalkyl having 1-8 carbon atoms in the alkyl chain,
A is alkanediyl or cycloalkanediyl and
Y is oxygen or sulfur.

In The definitions are the saturated ones or unsaturated Hydrocarbon chains, such as alkyl, alkanediyl, alkenyl or alkynyl, also in linkage with heteroatoms, such as in alkoxy, alkylthio or alkylamino, respectively straight-chain or branched.

halogen is generally for Fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular for fluorine or chlorine.

aryl stands for aromatic, mono- or polycyclic hydrocarbon rings, such as z. Phenyl, naphthyl, anthranyl, phenanthryl, preferably phenyl or naphthyl, especially phenyl.

cycloalkyl stands for saturated, carbocyclic, ring-shaped Compounds optionally with further carbocyclic, fused or bridged rings form a polycyclic ring system.

cycloalkenyl stands for carbocyclic, ring-shaped Compounds containing at least one double bond and optionally with other carbocyclic, fused or bridged rings form a polycyclic ring system.

Farther it has been found that the new amides of the general formula (I) a very good action against harmful organisms, especially one show strong fungicidal action.

The Compounds of the invention are optionally as mixtures of various possible isomeric forms, in particular of stereoisomers, such as. B. E and Z, cis or trans, threo and erythro, as well as optical isomers. It will be both the E and the Z isomers, as well as the threo- and erythro-, the optical isomers, as well as any mixtures of these isomers, Tautomers are described and claimed.

in welcher
R¹, R², und R³ gleich oder verschieden sind und unabhängig voneinander für Wasserstoff, Fluor, Chlor, Brom, Cyano, Nitro, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, n-Pentyl, n-Hexyl, n-Heptyl, Methoxy, Ethoxy, n- oder i-Propoxy, Methylthio, Ethylthio, n- oder i-Propylthio, Methylsulfinyl, Ethylsulfinyl, Methylsulfonyl oder Ethylsulfonyl, Trifluormethyl, Trifluorethyl, Difluormethoxy, Trifluormethoxy, Difluorchlormethoxy, Trifluorethoxy, Difluormethylthio, Difluorchlormethylthio, Trifluormethylthio, Trifluormethylsulfinyl oder Trifluormethylsulfonyl, Dimethylamino, Diethylamino, Acetyl, Propionyl, Methoxycarbonyl, Ethoxycarbonyl, Hydroximinomethyl, Hydroximinoethyl, Methoximinomethyl, Ethoximinomethyl, Methoximinoethyl oder Ethoximinoethyl, Cyclopropyl, Cyclobutyl, Cyclopentyl oder Cyclohexyl stehen, oder
R¹ und R² gemeinsam mit den Kohlenstoffatomen, an die sie gebunden sind, einen carbocyclischen Ring mit 5 oder 6 Ringgliedern bilden,
wobei R¹, R², und R³ nicht gleichzeitig für Wasserstoff stehen,
R^4a für Wasserstoff, Fluor, Chlor, Brom, Cyano, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, n-Pentyl, n-Hexyl, n-Heptyl, Allyl, Propargyl oder Trifluormethyl steht,
R⁵ und R⁶ gleich oder verschieden sind und unabhängig voneinander für Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, n-Pentyl, n-Hexyl, n-Heptyl,
Allyl, Methylallyl, Crotonyl, Propinyl oder Butinyl oder Cyanomethyl steht,
oder für gegebenenfalls durch Wasserstoff, Fluor, Chlor, Brom, Cyano, Nitro, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, n-Pentyl, n-Hexyl, n-Heptyl, Methoxy, Ethoxy, n- oder i-Propoxy, Methylthio, Ethylthio, n- oder i-Propylthio, Methylsulfinyl, Ethylsulfinyl, Methylsulfonyl oder Ethylsulfonyl, Trifluormethyl, Trifluorethyl, Difluormethoxy, Trifluormethoxy, Difluorchlormethoxy, Trifluorethoxy, Difluormethylthio, Difluorchlormethylthio, Trifluormethylthio, Trifluormethylsulfinyl oder Trifluormethylsulfonyl, Acetyl, Propionyl, Methoxycarbonyl, Ethoxycarbonyl, Hydroximinomethyl, Hydroximinoethyl, Methoximinomethyl, Ethoximinomethyl, Methoximinoethyl oder Ethoximinoethyl, Cyclopropyl, Cyclobutyl, Cyclopentyl oder Cyclohexyl substituiertes Benzyl steht,
A für Methandiyl, Ethan-1,1-diyl, Ethan-1,2-diyl, Propan-1,1-diyl, Propan-1,2-diyl, Propan-1,3-diyl, Propan-2,2-diyl, Butan-1,1-diyl, Butan-1,2-diyl, Butan-1,3-diyl, Butan-1,4-diyl, Butan-2,2-diyl, Butan-2,3-diyl, 1,1-Diethyletan-1,2-diyl, Cyclopropan-1,1-diyl oder Cyclopropan-1,2-diyl steht,
Y für Sauerstoff oder Schwefel steht und
G¹ für Sauerstoff, Schwefel oder N-R^7a steht, wobei
R^7a für Wasserstoff, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl steht.The invention preferably relates to compounds of the formula (Ia)

in which
R ¹ , R ² , and R ^{3 are the} same or different and are independently hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t Butyl, n-pentyl, n-hexyl, n-heptyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy , Trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, dimethylamino, diethylamino, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl or ethoximinoethyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, or
R ¹ and R ² together with the carbon atoms to which they are attached form a carbocyclic ring with 5 or 6 ring members,
where R ¹ , R ² and R ^{3 are} not simultaneously hydrogen,
R ^{4a is} hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-pentyl, n-hexyl, n-heptyl, allyl , Propargyl or trifluoromethyl,
R ⁵ and R ^{6 are} identical or different and are each independently methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-pentyl, n-hexyl, n-heptyl,
Allyl, methylallyl, crotonyl, propynyl or butynyl or cyanomethyl,
or optionally substituted by hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-pentyl, n-hexyl, n- Heptyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, Trifluoromethylsulfinyl or trifluoromethylsulfonyl, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl or ethoximinoethyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl substituted benzyl,
A is methanediyl, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, propane-2,2- diyl, butane-1,1-diyl, butane-1,2-diyl, butane-1,3-diyl, butane-1,4-diyl, butane-2,2-diyl, butane-2,3-diyl, 1,1-diethyl-1,2-diyl, cyclopropane-1,1-diyl or cyclopropane-1,2-diyl,
Y is oxygen or sulfur and
G ^{1 is} oxygen, sulfur or NR ^7a , where
R ^{7a is} hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.

in welcher
A, R¹, R², R³, R⁵, R⁶ und Y die gleiche Bedeutung haben, wie vorzugsweise für A, R¹, R², R³, R⁵, R⁶ und Y in Formel (1a) angegeben worden ist,
R^4b für Wasserstoff, Fluor, Chlor, Brom, Cyano, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, n-Pentyl, n-Hexyl, n-Heptyl, Allyl, Propargyl oder Trifluormethyl steht,
G² für Sauerstoff, Schwefel oder N-R^7b steht, wobei
R^7b für Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl steht.The invention likewise preferably relates to compounds of the formula (Ib)

in which
A, R ¹ , R ² , R ³ , R ⁵ , R ⁶ and Y have the same meaning as preferably indicated for A, R ¹ , R ² , R ³ , R ⁵ , R ⁶ and Y in formula (1a) has been,
R ^{4b is} hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-pentyl, n-hexyl, n-heptyl, allyl , Propargyl or trifluoromethyl,
G ^{2 is} oxygen, sulfur or NR ^7b , where
R ^{7b is} methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.

in welcher
A, R¹, R², R³, R⁵, R⁶ und Y die gleiche Bedeutung haben, wie vorzugsweise für A R¹, R², R³, R⁵, R⁶ und Y in Formel (1a) angegeben worden ist,
R^4c für Wasserstoff, Fluor, Chlor, Brom, Cyano, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, n-Pentyl, n-Hexyl, n-Heptyl, Allyl, Propargyl oder Trifluormethyl steht,
G³ für Sauerstoff, Schwefel oder N-R^7c steht, wobei
R^7c für für Wasserstoff, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl steht.The invention furthermore preferably relates to compounds of the formula (Ic)

in which
A, R ¹ , R ² , R ³ , R ⁵ , R ⁶ and Y have the same meaning as has preferably been given for AR ¹ , R ² , R ³ , R ⁵ , R ⁶ and Y in formula (1a) .
R ^{4c is} hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-pentyl, n-hexyl, n-heptyl, allyl , Propargyl or trifluoromethyl,
G ^{3 is} oxygen, sulfur or NR ^7c , where
R ^{7c is} hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.

in welcher
A, R¹, R², R³, R⁵, R⁶ und Y die gleiche Bedeutung haben, wie vorzugsweise für A, R¹, R², R³, R⁵, R⁶ und Y in Formel (1a) angegeben worden ist,
R^4d für Wasserstoff, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl steht,
G⁴ für Sauerstoff, Schwefel oder N-R^7d steht, wobei
R^7d für Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl steht.The invention further preferably compounds of formula (Id),

in which
A, R ¹ , R ² , R ³ , R ⁵ , R ⁶ and Y have the same meaning as preferably for A, R ¹ , R ² , R ³ , R ⁵ , R ⁶ and Y in Formula (1a) has been specified,
R ^{4d is} hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,
G ^{4 is} oxygen, sulfur or NR ^7d , where
R ^{7d is} methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.

in welcher
A, R¹, R², R³, R⁵, R⁶ und Y die gleiche Bedeutung haben, wie vorzugsweise für A R¹, R², R³, R⁵, R⁶ und Y in Formel (1a) angegeben worden ist,
G⁵ für Sauerstoff, Schwefel oder N-R^7e steht, wobei
R^7e für Wasserstoff, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl steht.The invention further preferably compounds of formula (Ie),

in which
A, R ¹ , R ² , R ³ , R ⁵ , R ⁶ and Y have the same meaning as has preferably been given for AR ¹ , R ² , R ³ , R ⁵ , R ⁶ and Y in formula (1a) .
G ^{5 is} oxygen, sulfur or NR ^7e , where
R ^{7e is} hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.

in welcher
A, R¹, R², R³, R⁵, R⁶ und Y die gleiche Bedeutung haben, wie vorzugsweise für A, R¹, R², R³, R⁵, R⁶ und Y in Formel (1a) angegeben worden ist,
G⁶ für Sauerstoff, Schwefel oder N-R^7f steht, wobei
R^7f für Wasserstoff Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl steht.The invention further preferably compounds of the formula (If),

in which
A, R ¹ , R ² , R ³ , R ⁵ , R ⁶ and Y have the same meaning as preferably indicated for A, R ¹ , R ² , R ³ , R ⁵ , R ⁶ and Y in formula (1a) has been,
G ^{6 is} oxygen, sulfur or NR ^7f , where
R ^{7f is} hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.

in welcher
A, R¹, R², R³, R⁵, R⁶ und Y die gleiche Bedeutung haben, wie vorzugsweise für A, R¹, R², R³, R⁵, R⁶ und Y in Formel (1a) angegeben worden ist,
G⁷ für Sauerstoff, Schwefel oder N-R^7g steht, wobei
R^7g für Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl steht.The invention further preferably compounds of the formula (Ig),

in which
A, R ¹ , R ² , R ³ , R ⁵ , R ⁶ and Y have the same meaning as preferably indicated for A, R ¹ , R ² , R ³ , R ⁵ , R ⁶ and Y in formula (1a) has been,
G ^{7 is} oxygen, sulfur or NR ^7g , where
R ^{7g is} methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.

In the formulas (Ia), (Ib), (Ic), (Id), (Ie), (If), (Ig) A, R ¹ , R ² , R ³ , R ⁵ , R ⁶ and Y have the the following particularly preferred meanings:
R ¹ , R ² , and R ³ are identical or different and, more particularly, independently of one another, are particularly preferably hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s or t-butyl, n-pentyl, n-hexyl, n-heptyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl , trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl, dimethylamino, diethylamino, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, Hydroximinomethyl, Hydroximinoethyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl or ethoximinoethyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, or
R ¹ and R ² together with the carbon atoms to which they are attached form a carbocyclic ring with 5 or 6 ring members.
R ¹ , R ² , and R ³ are not hydrogen at the same time.
A particularly preferably represents methanediyl, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl or propane-2 , 2-diyl.
Y is particularly preferably oxygen.
R ⁵ and R ⁶ are identical or different and are, with particular preference independently of one another, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-pentyl, n-hexyl, n- Heptyl, allyl, methylallyl, crotonyl, propynyl or butynyl or cyanomethyl.

In formula (Ia)
R ^{4a is} particularly preferably hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-heptyl trifluoromethyl, chlorine or cyano and
G ¹ particularly preferred for oxygen, sulfur or NR ^7a , wherein
R ^7a particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.

In formula (Ib) stand
R ^4b particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, chlorine or cyano and
G ² particularly preferably represents oxygen, sulfur or NR ^7b , where
R ^7b particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.

In formula (Ic)
R ^4c particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-heptyl, trifluoromethyl, chlorine or cyano and
G ³ particularly preferred for oxygen, sulfur or NR ^7c , wherein
R ^7c particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.

In formula (Id) stand
R ^4d particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-heptyl trifluoromethyl, chlorine or cyano and
G ⁴ particularly preferred for oxygen, sulfur or NR ^7d , wherein
R ^7d particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.

In formula (Ie) stands
G ⁵ particularly preferably represents oxygen, sulfur or NR ^7e , where
R ^7e particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.

In formula (If)
G ⁶ particularly preferably represents oxygen, sulfur or NR ^7f , where
R ^7f particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.

In formula (Ig)
G ⁷ particularly preferably represents oxygen, sulfur or NR ^7g , where
R ^7g particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.

The listed above general or preferred radical definitions apply to both the end products of formula (I) as well as corresponding to each required for the preparation of starting materials or intermediates.

The in the respective combinations or preferred combinations of Remains in detail for this Residues given radical definitions are independent of the respective specified Combination, arbitrarily also by remaining definitions of other preferential ranges replaced.

• a) Carbonsäurederivate der allgemeinen Formel (II)
  
  in welcher R¹, R², R³ und R⁴ die oben angegebenen Bedeutungen haben und T für Hydroxy, Halogen oder Alkoxy steht, mit einem Amin der allgemeinen Formel (III)
  
  in welcher R⁵, R⁶ und A die oben angegebenen Bedeutungen haben, – oder mit einem Säureadditionskomplex hiervon – gegebenenfalls in Gegenwart eines Säureakzeptors, gegebenenfalls in Gegenwart eines Kondensationsmittels, gegebenenfalls in Gegenwart eines Katalysators und gegebenenfalls in Gegenwart eines Verdünnungsmittels, umsetzt oder wenn man
• b) Amide der Formel (I) mit Y in seiner Bedeutung als Sauerstoff mit einem Schwefelungsreagenz, gegebenenfalls in Gegenwart eines Verdünnungsmittels, umsetzt.

Finally, it has been found that one obtains the amides of the general formula (I), if one

• a) carboxylic acid derivatives of the general formula (II)
  
  in which R ¹ , R ² , R ³ and R ^{4 have} the meanings given above and T is hydroxyl, halogen or alkoxy, with an amine of the general formula (III)
  
  in which R ⁵ , R ⁶ and A have the abovementioned meanings, - or with an acid addition complex thereof - optionally in the presence of an acid acceptor, if appropriate in the presence of a condensing agent, if appropriate in the presence of a catalyst and optionally in the presence of a diluent, or if
• b) amides of the formula (I) with Y in its meaning as oxygen with a sulfurizing reagent, if appropriate in the presence of a diluent, is reacted.

If, for example, 3- (4-chlorophenyl) -5-methylisoxazole-4-carbonyl chloride and (4-ethoxy-3-methoxybenzyl) amine are used as starting materials, the course of process (a) according to the invention can be illustrated by the following formula scheme:

For carrying out the process a) required as starting materials carboxylic acid derivatives are generally defined by the formula (II). In this formula (II) R ^1, R ^2, R ³ and R ⁴ have preferably or in particular have those meanings which have as preferred in connection with the description of the compounds of formula (I) according to the invention or particularly preferred for R ¹ , R ² , R ³ and R ^{4 were} given; T is preferably alkoxy having 1 to 4 carbon atoms, in particular methoxy or ethoxy, hydroxy or chlorine.

The starting materials of the formula (II) are known and / or can be prepared by processes known per se (compare, for example, J. Org. Chem. 27 (1962) 4305, J. Chem. Soc. (1963) 5838, J. Chem. Soc. (1963) 5845; Chem. Ber. 106, 3275 (1973); US 3,479,365 ; US 3,551,440 ; J. Org. Chem. (1967) 32 (10) 3132; Tetrahedron 25, (1969), 389; Synthetic Com. (1987), 17 (2), 165; EP 352581 ; EP 352581 ; EP 1186598 ; Bioor. & Medicinal Chem. Lett., 11 (5), 641 (2001); JP 20011011060 ; JP 2001011059 ; EP 352581 ; Tet. Lett. 23, (2), 235 (1982); J. of Org. Chem. 55 (13), 4011 (1990); EP 352581 ; EP 3252581 ; Synthesis, (1), 64 (1996); GB 1,058,384; US 3,257,411 ; J. Am. Chem. Soc. (1969), 89 (21), 5462; J. Org. Chem. (1967), 27, 4305; US 4,380,465 ; Ber. 105, (1972) 196; Tetrahedron Letters 17, (1971), 1281; WO95 / 04724; CH 502365 ; EP 785193 ; Heterocycles (2000), 53 (1), 159; Aust. J. Chem. (1994), 47, 1375; Bulletin of the Soc. Chim. Belges (1996), 105 (1), 33; Bulletin of the Soc. Chim. Belges (1996), 105 (4), 189).

The further required for carrying out the process a) according to the invention as starting materials amines are generally defined by the formula (III). In this formula (III), A, R ⁵ and R ⁶ preferably, or in particular those meanings, already in connection with the description of the compounds of formula (I) as preferred or as particularly preferred for R ⁵ and R ⁶ were specified.

The Amines of formula (III) are partially known organic synthetic chemicals and / or can after be prepared per se known methods.

in welcher
A und R⁵ die oben angegebenen Bedeutungen haben und
R⁸ für Allyl, Propargyl, 2-Butinyl oder Cyanmethyl steht
und (III-b)

in welcher
A und R⁶ die oben angegebenen Bedeutungen haben und
R⁹ für Allyl, Propargyl, 2-Butinyl oder Cyanmethyl steht.New and likewise subject matter of the invention are amines of the formulas (III-a)

in which
A and R ^{5 have} the meanings given above and
R ^{8 is} allyl, propargyl, 2-butynyl or cyanomethyl
and (III-b)

in which
A and R ^{6 have} the meanings given above and
R ^{9 is} allyl, propargyl, 2-butynyl or cyanomethyl.

in welcher
A und R⁵ die oben angegebenen Bedeutungen haben,
bzw. Hydroxyverbindungen der allgemeinen Formel (IV-b)

in welcher
A und R⁶ die oben angegebenen Bedeutungen haben,
mit Allyl-, Propargyl-, 2-Butinyl-chlorid, -bromid oder -iodid oder Chlor- Brom- oder Iodacetonitril, gegebenenfalls in Gegenwart eines Verdünnungsmittels, wie beispielsweise Acetonitril, und gegebenenfalls in Gegenwart eines Säureakzeptors, wie beispielsweise Kaliumcarbonat, umsetzt.The amines of the formulas (III-a) and (III-b) are obtained (process c) when hydroxy compounds of the general formula (IV-a)

in which
A and R ^{5 have} the meanings given above,
or hydroxy compounds of the general formula (IV-b)

in which
A and R ^{6 have} the meanings given above,
with allyl, propargyl, 2-butynyl chloride, bromide or iodide or chloro-bromo or iodoacetonitrile, optionally in the presence of a diluent, such as acetonitrile, and optionally in the presence of an acid acceptor, such as potassium carbonate.

in welcher
R⁵ bzw. R⁶ die oben angegebenen Bedeutungen haben und
PG für die Schutzgrupe steht.The amino group of the compounds of formula (IV-a) and (IV-b) is given prior to alkylation if provided with a conventional amines protection group, such as t-butoxy carbonyl, by conventional methods. This gives compounds of the formula (IV-a *), or (IV-b *)

in which
R ⁵ and R ^{6 have} the meanings given above and
PG stands for the protection group.

in welchen
R⁸, R⁹, PG, sowie R⁵ bzw. R⁶ die oben angegebenen Bedeutungen haben,
führt, wird die Schutzgruppe nach üblichen Methoden wieder abgespalten (siehe auch die Herstellungsbeispiele).After the alkylation reaction which initially leads to compounds of the formula (III-a *) or (III-b *)

in which
R ⁸ , R ⁹ , PG, and R ⁵ and R ^{6 have} the meanings given above,
leads, the protective group is cleaved again by conventional methods (see also the preparation examples).

If, for example, 4- (aminomethyl) -2-methoxyphenol and allyl bromide are used as starting materials, the course of process (c) according to the invention can be illustrated by the following formula scheme:

The hydroxy compounds required as starting materials for carrying out the process c) according to the invention are generally defined by the formula (IV-a). In this formula (IV-a), R ⁵ preferably or in particular has the meaning which has already been mentioned in connection with the description of the compounds of the formula (I) according to the invention as being preferred or particularly preferred for R ⁵ .

The hydroxy compounds of formula (IV-a) are commercially available synthetic chemicals or can be obtained by known methods (see, for example, J. Chem. Soc., 127 (1925), 560 and J. Amer. Chem. Soc., 72 (1950), 2781; JP 11130739 or DE 19958165 ).

The hydroxy compounds required alternatively as starting materials for carrying out the process c) according to the invention are generally defined by the formula (IV-b). In this formula (IV-b), R ⁶ preferably or in particular has the meaning which has already been mentioned in connection with the description of the compounds of the formula (I) according to the invention as being preferred or particularly preferred for R ⁶ .

The Hydroxy compounds of the formula (IV-b) are commercially available synthetic chemicals or can after known methods are obtained (see, for example, Ger. 4322065; J. Org. Chem, 53 (5), 1064-71 (1988); Synth. Comm., 7 (1), 71-8 (1977)).

The to carry out the method according to the invention c) furthermore compounds required as starting materials allyl, Propargyl, 2-butynyl chloride, bromide or iodide or chlorine-bromine or iodoacetonitrile are common synthetic chemicals.

If, for example, 3- (4-chlorophenyl) -N- (4-ethoxy-3-methoxybenzyl) -5-methylisoxazole-4-carboxamide and phosphorus pentasulfide are used as starting materials, the course of process (b) according to the invention can be illustrated by the following formula scheme become:

The to carry out the method according to the invention b) required as starting materials Amides are compounds of the invention and can according to the inventive method a) are obtained.

When Sulfurizing agent to carry out the method according to the invention b) all reagents that are capable of carbon are eligible exchange bound oxygen atoms for sulfur atoms, such as e.g. Hydrogen sulfide, phosphorus pentasulfide or Lawesson's reagent.

hydrogen sulfide, Phosphorus pentasulfide or Lawesson's reagent are commercial synthetic chemicals.

The inventive method a) is optionally carried out in the presence of a diluent. When such are water and organic solvents into consideration. For this belong in particular aliphatic, alicyclic or aromatic, if appropriate halogenated hydrocarbons, such as gasoline, benzene, Toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, Dichloromethane, chloroform, carbon tetrachloride, ethers, such as diethyl ether, Diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones, such as acetone, butanone or methyl isobutyl ketone; nitrites, such as acetonitrile, propionitrile or benzonitrile; Amides, such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoramide; Esters such as methyl acetate or ethyl acetate, Sulfoxides, such as dimethyl sulfoxide, alcohols, such as methanol, ethanol, n- or i-propanol, Ethylene glycol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, Diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, whose Mixtures with water or pure water.

The inventive method a) is optionally in the presence of a suitable acid acceptor carried out. As such, all the usual inorganic or organic bases in question. These include, for example Alkaline earth metal or alkali metal hydrides, hydroxides, amides, alkoxides, acetates, carbonates or bicarbonates, such as Sodium hydride, sodium amide, sodium methoxide, sodium ethylate, potassium tert-butylate, 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, as well as tertiary Amines, such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, N, N-dimethylbenzylamine, pyridine, N-methylpiperidine, N, N-dimethylaminopyridine, Diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU).

The inventive method a) is optionally in the presence of a suitable condensing agent carried out. As such, everyone usually comes for such Amidation reactions usable condensing agent in question. Examples which may be mentioned are 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, Isobutyl chloroformate or methanesulfonyl chloride; Carbodiimides, such as N, N'-dicyclohexylcarbodiimide (DCC) or other usual Condensing agents such as phosphorus pentoxide, polyphosphoric acid, N, N'-carbonyldiimidazole, 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ) or triphenylphosphine / carbon tetrachloride.

The inventive method a) is optionally carried out in the presence of a catalyst. For example may be mentioned 4-dimethylaminopyridine, 1-hydroxy-benzotriazole or Dimethylformamide.

The Reaction temperatures can during execution the method according to the invention a) in a larger area be varied. In general, one works at temperatures between -50 ° C and + 150 ° C, preferably at temperatures between -20 ° C and 150 ° C.

to execution the method according to the invention a) is used per mole of carboxylic acid derivative of the formula (II) is generally 1 to 5 mol, preferably 1.0 to 2.5 moles of amine.

The inventive method a) can also be carried out as a two-stage process. Here are the Carboxylic acid derivatives the general formula (II) first converted into an activated form and in a subsequent Step with the amines of the general formula (III) to the amides of the invention implemented general formula (I).

When activated form of the carboxylic acid derivatives of formula (II) are all carboxy-activated derivatives in question, such as. halides, preferably acid chlorides, azides, furthermore symmetrical and mixed anhydrides, such as the mixed o-alkylcarbonic anhydrides, further activated esters, e.g. p-Nitrophenylester or N-Hydroxisuccinimidester as well as adducts with condensing agents, e.g. dicyclohexylcarbodiimide or in situ generated activated forms of the carboxylic acids.

When thinner to carry out the method according to the invention b) all inert organic solvents are suitable. For this belong preferably aliphatic, alicyclic or aromatic hydrocarbons, such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, Toluene, xylene or decalin; halogenated hydrocarbons, such as For example, 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.

The Reaction temperatures can during execution the method according to the invention b) in a wider area be varied. In general, one works at temperatures of 0 ° C to 150 ° C, preferably at temperatures of 0 ° C up to 80 ° C.

to execution the method according to the invention b) for the preparation of the compounds of formula (I) is set pro Mol of the amide of formula (I) with Y in its meaning as oxygen in general from 0.1 to 15 mol, preferably 0.5 to 8 mol sulfurizing reagent one.

The Reaction is carried out Workup and isolation of the reaction products is carried out according to known Process (see also the production examples).

The inventive method are generally carried out under atmospheric pressure. However, it is also possible under increased or reduced pressure - in general between 0.1 bar and 10 bar - to work.

The Reaction is carried out Workup and isolation of the reaction products is carried out according to known Method.

The Inventive substances have a strong microbicidal action and can be used to combat undesirable Microorganisms, such as fungi and bacteria, in crop protection and be used in the protection of materials.

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

bactericidal can be used in crop protection to control Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae deploy.

By way of example but not limitation, some pathogens of fungal and bacterial diseases, which fall under the above-enumerated generic terms, are named:
Xanthomonas species, such as Xanthomonas campestris pv. Oryzae;
Pseudomonas species, such as Pseudomonas syringae pv. Lachrymans;
Erwinia species, such as Erwinia amylovora;
Pythium species such as Pythium ultimum;
Phytophthora species, such as Phytophthora infestans;
Pseudoperonospora species, such as Pseudoperonospora humuli or
Pseudoperonospora cubensis;
Plasmopara species, such as Plasmopara viticola;
Bremia species, such as Bremia lactucae;
Peronospora species such as Peronospora pisi or P. brassicae;
Erysiphe species, such as Erysiphe graminis;
Sphaerotheca species, such as Sphaerotheca fuliginea;
Podosphaera species, such as Podosphaera leucotricha;
Venturia species, such as Venturia inaequalis;
Pyrenophora species, such as, for example, Pyrenophora teres or P. graminea
(Conidia form: Drechslera, Syn: Helminthosporium);
Cochliobolus species, such as Cochliobolus sativus
(Conidia form: Drechslera, Syn: Helminthosporium);
Uromyces species, such as Uromyces appendiculatus;
Puccinia species, such as Puccinia recondita;
Sclerotinia species, such as Sclerotinia sclerotiorum;
Tilletia species, such as Tilletia caries;
Ustilago species such as Ustilago nuda or Ustilago avenae;
Pellicularia species, such as, for example, Pellicularia sasakii;
Pyricularia species, such as Pyricularia oryzae;
Fusarium species such as Fusarium culmorum;
Botrytis species, such as Botrytis cinerea;
Septoria species such as Septoria nodorum;
Leptosphaeria species, such as Leptosphaeria nodorum;
Cercospora species, such as Cercospora canescens;
Alternaria species, such as Alternaria brassicae;
Pseudocercosporella species, such as Pseudocercosporella herpotrichoides.

The active ingredients according to the invention also have a strong restorative Effect in plants. They are therefore suitable for mobilization plant's own defenses against infestation by unwanted Microorganisms.

Under plant-strengthening (resistance-inducing) substances are in the present context to understand such substances that are capable of the immune system of plants to stimulate so that the treated plants at subsequent inoculation with unwanted microorganisms extensive resistance unfold against these microorganisms.

Under undesirable Microorganisms in the present case are phytopathogenic fungi, To understand bacteria and viruses. The substances according to the invention can So be used to plants within a period of time after the treatment against the infestation by the mentioned pathogens to protect. The period within which protection is provided extends in the general from 1 to 10 days, preferably 1 to 7 days after Treatment of plants with the active ingredients.

The good plant tolerance the active ingredients in the fight of plant diseases necessary concentrations allows one Treatment of above-ground parts of plants, planting and seed, and the soil.

In this case, the active compounds according to the invention can be used with particularly good success for combating diseases in the cultivation of wine, fruit and vegetables, for example against Alternaria, Phytophtora and Plasmopara species
The active compounds according to the invention are also suitable for increasing crop yield. They are also low toxicity and have good plant tolerance.

The active ingredients according to the invention can optionally in certain concentrations and application rates also as herbicides, for influencing plant growth, as well as for fight of animal pests be used. Where appropriate, they may also be considered as intermediate and precursors for use the synthesis of other drugs.

According to the invention, all plants and parts of plants can be treated. In this context, plants are understood as meaning all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants can be plants that can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including plant varieties which can or can not be protected by plant variety rights. Plant parts are to be understood as meaning all aboveground and subterranean parts and organs of the plants, such as shoot, leaf, flower and root, examples of which include leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds, and roots, tubers and rhizomes. The plant parts also include crops and vegetative and generative propagation material, such as cuttings, tubers, rhizomes, offshoots and seeds.

The Treatment according to the invention the plants and plant parts with the active ingredients are made directly or by affecting their environment, habitat or storage space the usual Treatment methods, e.g. by dipping, spraying, evaporating, misting, Sprinkle, spread and propagate material, in particular in seeds, further by single or multi-layer wrapping.

in the Material protection can be the substances of the invention for the protection of industrial materials against Infestation and destruction by unwanted Use microorganisms.

Under technical materials are non-living in the present context Understand materials for the use has been prepared in the art. For example can technical materials, by the active compounds according to the invention before microbial change or destruction protected adhesives, glues, paper and board, textiles, Leather, wood, paints and plastics, coolants and other materials that are infested by microorganisms or can be decomposed. As part of the protected Materials are also parts of production plants, such as cooling water circuits, called, which can be affected by the proliferation of microorganisms. As part of of the present invention are preferred as engineering materials Adhesives, glues, papers and cartons, leather, wood, paints, coolant and heat transfer fluids called, more preferably wood.

When Microorganisms that cause degradation or alteration of engineering materials can cause are for example bacteria, fungi, yeasts, algae and slime organisms called. The active compounds according to the invention preferably act against fungi, especially molds, wood-discolouring and wood-destroying fungi (Basidiomycetes) and against slime organisms and algae.

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

The Active ingredients can dependent on from their respective physical and / or chemical properties in the usual Formulations are transferred, like solutions, Emulsions, suspensions, powders, foams, pastes, granules, aerosols, Very fine encapsulation in polymeric substances and in encapsulants for seeds, as well as ULV cold and warm mist formulations.

These formulations are prepared in a known manner, for example by mixing the active compounds with extenders, ie liquid solvents, liquefied gases under pressure and / or solid carriers, optionally with the use of surface-active agents, ie emulsifiers and / or dispersants and / or foam-forming agents. In the case of using water as extender, for example, organic solvents can also be used as auxiliary solvents. Suitable liquid solvents are essentially: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, alcohols, such as butanol or glycol and their Ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, as well as water. By liquefied gaseous diluents or carriers are meant those liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellants, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide. Suitable solid carriers are: for example ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided silica, alumina and silicates. As solid carriers for granules are: for example, broken and fractionated natural rocks such as calcite, pumice, marble, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stalks. Suitable emulsifiers and / or foam-formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates and protein hydrolysates. Suitable dispersants are: for example lignin-sulphite liquors and methylcellulose.

It can in the formulations adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-shaped Polymers such as gum arabic, polyvinyl alcohol, Polyvinyl acetate, as well as natural Phospholipids, such as cephalins and lecithins, and synthetic phospholipids. Further Additives can mineral and vegetable oils be.

It can Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, Ferrocyan blue and organic dyes such as alizarin, azo and Metal phthalocyanine dyes and trace nutrients, such as salts of iron, Manganese, boron, copper, cobalt, molybdenum and zinc are used.

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

The active ingredients according to the invention can as such or in their formulations also in mixture with known Fungicides, bactericides, acaricides, nematicides or insecticides used, e.g. to widen the spectrum of action or to prevent development of resistance. In many cases you get it synergistic effects, i. the effectiveness of the mixture is greater than the effectiveness of the individual components.

When Mischpartner come, for example, the following compounds in question:

fungicides:

2-phenylphenol; 8-hydroxyquinoline sulfate;
Acibenzolar-S-methyl; aldimorph; amidoflumet; Ampropylfos; Ampropylfos-potassium; andoprim; anilazine; azaconazole; azoxystrobin;
benalaxyl; Benodanil; benomyl; Benthiavalicarb-isopropyl; Benzamacril; Benzamacril isobutyl; bilanafos; binapacryl; biphenyl; bitertanol; Blasticidin-S; bromuconazole; Bupirimate; Buthiobate; butylamine;
Calcium polysulfides; capsimycin; captafol; captan; carbendazim; carboxin; carpropamid; carvones; chinomethionat; Chlobenthiazone; Chlorfenazole; chloroneb; chlorothalonil; chlozolinate; Clozylacon; cyazofamid; cyflufenamid; cymoxanil; cyproconazole; cyprodinil; cyprofuram;
Dagger G; debacarb; dichlofluanid; dichlone; dichlorophen; diclocymet; Diclomezine; dicloran; diethofencarb; Difenoconazole; diflumetorim; dimethirimol; dimethomorph; dimoxystrobin; diniconazole; Diniconazole-M; dinocap; diphenylamines; Dipyrithione; Ditalimfos; dithianon; dodine; Drazoxolon;
edifenphos; epoxiconazole; ethaboxam; ethirimol; etridiazole;
famoxadone; fenamidone; Fenapanil; fenarimol; Fenbuconazole; fenfuram; fenhexamid; Fenitropan; fenoxanil; fenpiclonil; fenpropidin; fenpropimorph; ferbam; fluazinam; Flubenzimine; fludioxonil; flumetover; flumorph; fluoromides; fluoxastrobin; fluquinconazole; flurprimidol; flusilazole; flusulfamide; flutolanil; flutriafol; folpet; Fosetyl-Al; Fosetyl-sodium; fuberidazole; furalaxyl; furametpyr; Furcarbanil; Furmecyclox;
guazatine;
Hexachlorobenzene; hexaconazole; hymexazol;
imazalil; Imibenconazole; Iminoctadine triacetate; Iminoctadine tris (albesil; iodocarb; ipconazole; ipropose; iprodione; iprovalicarb; irumamycin; isoprothiolane; isovaledione;
kasugamycin; Kresoxim-methyl;
mancozeb; maneb; Meferimzone; mepanipyrim; mepronil; metalaxyl; Metalaxyl-M; metconazole; methasulfocarb; Methfuroxam; metiram; metominostrobin; Metsulfovax; mildiomycin; myclobutanil; myclozoline;
natamycin; nicobifen; Nitro Thal-isopropyl; Noviflumuron; nuarimol;
ofurace; orysastrobin; oxadixyl; Oxolinic acid; Oxpoconazole; oxycarboxin; Oxyfenthiin;
paclobutrazol; Pefurazoate; penconazole; pencycuron; phosdiphen; phthalides; picoxystrobin; piperalin; Polyoxins; Polyoxorim; Probenazole; prochloraz; procymidone; propamocarb; Propanosine-sodium; propiconazole; propineb; proquinazid; prothioconazole; pyraclostrobin; Pyrazohos; pyrifenox; pyrimethanil; pyroquilon; Pyroxyfur; Pyrrolnitrine;
Quinconazole; quinoxyfen; quintozene;
Simeconazole; spiroxamine; Sulfur;
tebuconazole; tecloftalam; Tecnazene; Tetcyclacis; tetraconazole; thiabendazole; Thicyofen; Thifluzamide; Thiophanate-methyl; thiram; Tioxymid; Tolclofos-methyl; tolylfluanid; triadimefon; triadimenol; Triazbutil; triazoxide; Tricyclamide; Tricyclazole; tridemorph; trifloxystrobin; triflumizole; triforine; triticonazole;
Uniconazole;
Validamycin A; vinclozolin;
Zineb; ziram; zoxamide;
(2S) -N- [2- [4 - [[3- (4-chlorophenyl) -2-propynyl] oxy] -3-methoxyphenyl] ethyl] -3-methyl-2 - [(methylsulfonyl) amino] butanamide ;
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-pyridinecarboxamides;
3,4,5-trichloro-2,6-pyridinedicarbonitrile;
Actinovate;
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;
Monokaliumcarbonat;
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 mixture; copper; copper naphthenate; copper oxychloride; Copper sulfate; Cufraneb; copper; mancopper; Oxine-copper.

bactericides:

bronopol, Dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, Octhilinone, furancarboxylic acid, Oxytetracycline, probenazole, streptomycin, tecloftalam, copper sulfate and other copper preparations.

Insecticides / acaricides / nematicides:

Abamectin, ABG-9008, acephate, acequinocyl, acetamiprid, acetoprole, acrinathrin, AKD-1022, AKD-3059, AKD-3088, alanycarb, aldicarb, aldoxycarb, allethrin, alpha-cypermethrin (alphamethrin), amidoflumet, aminocarb, amitraz, avermectin , AZ-60541, azadirachtin, azamethiphos, azinphos-methyl, azinphos-ethyl, azocyclotin,
Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillus thuringiensis, Bacillus thuringiensis strain EG-2348, Bacillus thuringiensis strain GC-91, Bacillus thuringiensis strain NCTC-11821, Baculoviruses, Beauveria bassiana, Beauveria tenella, Benclothiaz, Bendiocarb, Benfuracarb, Bensultap, Benzoximate , Beta-Cyfluthrin, Beta-Cypermethrin, Bifenazate, Bifenthrin, Binapacryl, Bioallethrin, Bioallethrin-S-cyclopentyl-isomer, Bioethanomethrin, Biopermethrin, Bioresmethrin, Bistrifluron, BPMC, Brofenprox, Bromophos-ethyl, Bromopropylate, Bromfenvinfos (-methyl), BTG -504, BTG-505, Bufencarb, Buprofezin, Butathiofos, Butocarboxim, Butoxycarboxim, Butylpyridaben,
Cadusafos, camphechlor, carbaryl, carbofuran, carbophenothione, carbosulfan, cartap, CGA-50439, quinomethionate, chlordane, chlordimeform, chloethocarb, chloroethoxyfos, chlorfenapyr, chlorfenvinphos, chlorofluorazuron, chlormephos, chlorobenzilates, chloropicrin, chlorproxyfen, chlorpyrifos-methyl, chlorpyrifos (-ethyl ), Chlovaporthrin, chromafenozide, cis-cypermethrin, cis-resmethrin, cis-permethrin, clocythrin, cloethocarb, clofentezine, clothianidin, clothiazoben, codlemone, coumaphos, cyanofenphos, cyanophos, cycloprene, cycloprothrin, cydia pomonella, cyfluthrin, cyhalothrin, cyhexatin, cypermethrin , Cyphenothrin (1R-trans-isomer), Cyromazine,
DDT, deltamethrin, demeton-S-methyl, demeton-S-methyl sulphone, diafenthiuron, dialifos, diazinon, dichlorofenthione, dichlorvos, dicofol, dicrotophos, dicyclanil, diflubenzuron, dimefluthrin, dimethoates, dimethylvinphos, dinobutone, dinocap, dinotefuran, diofenolane, disulfonyl, Docusate-sodium, Dofenapine, DOWCO-439,
Eflusilanate, emamectin, emamectin benzoate, empenthrin (1R isomer), endosulfan, entomopthora spp., EPN, Esfenvalerate, Ethiofencarb, Ethiprole, Ethion, Ethoprophos, Etofenprox, Etoxazole, Etrimfos,
Famphur, Fenamiphos, Fenazaquin, Fenbutatin oxide, Fenfluthrin, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxacrim, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyrithrin, Fenpyroximate, Fensulfothion, Fenthion, Fentrifanil, Fenvalerate, Fipronil, Flonicamide, Fluacrypyrim, Fluazuron, Flubenzimines, Flubrocythrinates, Flucycloxuron , Flucythrinate, Flufenerim, Flufenoxuron, Flufenprox, Flumethrin, Flupyrazofos, Flutenzine (Flufenzine), Fluvalinate, Fonofos, Formetanate, Formothion, Fosmethilane, Fosthiazate, Fubfenprox (Fluproxyfen), Furathiocarb,
Gamma-cyhalothrin, gamma-HCH, gossyplure, grandlure, granulosis viruses,
Halfenprox, Halofenozide, HCH, HCN-801, Heptenophos, Hexaflumuron, Hexythiazox, Hydramethylnone, Hydroprene,
IKA-2002, Imidacloprid, Imiprothrin, Indoxacarb, Iodofenphos, Iprobenfos, Isazofos, Isofenphos, Isoprocarb, Isoxathion, Ivermectin,
Japonilure,
Kadethrin, nuclear poly-derviruses, kinoprene,
Lambda-Cyhalothrin, Lindane, Lufenuron,
Malathion, mecarbam, mesulfenfos, metaldehyde, metam-sodium, methacrifos, methamidophos, metharhizium anisopliae, metharhizium flavoviride, methidathion, methiocarb, methomyl, methoprene, methoxychlor, methoxyfenozide, metofluthrin, metolcarb, metoxadiazone, mevinphos, milbemectin, milbemycin, MKI-245, MON-45700, monocrotophos, moxidectin, 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, Noviflumuron,
OK-5101, OK-5201, OK-9601, OK-9602, OK-9701, OK-9802, Omethoate, Oxamyl, Oxydemeton-methyl,
Paecilomyces fumosoroseus, parathion-methyl, parathion (-ethyl), permethrin (cis-, trans-), petroleum, PH-6045, phenothrin (1R-trans isomer), phenthoates, phorates, phosalones, phosmet, phosphamidone, phosphocarb, phoxim, Piperonyl butoxides, Pirimicarb, Pirimiphos-methyl, Pirimiphos-ethyl, Potassium oleates, Prallethrin, Profenofos, Profuthrin, Promecarb, Propaphos, Propargites, Propetamphos, Propoxur, Prothiofos, Prothoates, Protrifenbute, Pymetrozines, Pyraclofos, Pyresmethrin, Pyrethrum, Pyridaben, Pyridalyl, Pyridaphenthione, Pyridathion, Pyrimidifen, Pyriproxyfen,
quinalphos,
Resmethrin, RH-5849, Ribavirin, RU-12457, RU-15525,
S-421, S-1833, Salithion, Sebufos, SI-0009, Silafluofen, Spinosad, Spirodiclofen, Spiromesifen, Sulfluramid, Sulfotep, Sulprofos, SZI-121,
Tau Fluvalinate, Tebufenozide, Tebufenpyrad, Tebupirimfos, Teflubenzuron, Tefluthrin, Temephos, Temivinphos, Terbam, Terbufos, Tetrachlorvinphos, Tetradifon, Tetramethrin, Tetramethrin (1R-isomer), Tetrasul, Theta-Cypermethrin, Thiacloprid, Thiamethoxam, Thiapronil, Thiatriphos, Thiocyclam hydrogen oxalate, thiodicarb, thiofanox, thiometone, thiosultap-sodium, thuringiensin, tolfenpyrad, tralocythrin, tralomethrin, transfluthrin, triarathene, triazamates, triazophos, triazuron, trichlophenidines, trichlorfone, trichloroermatitis, triflumuron, trimethacarb,
Vamidothion, Vaniliprole, Verbutin, Verticillium lecanii,
WL-108477, WL-40027,
YI-5201, YI-5301, YI-5302,
XMC, xylylcarb,
ZA-3274, zeta-cypermethrin, zolaprofos, ZXI-8901,
the compound 3-methyl-phenyl-propylcarbamate (Tsumacide Z),
the compound 3- (5-chloro-3-pyridinyl) -8- (2,2,2-trifluoroethyl) -8-azabicyclo [3.2.1] octane-3-carbonitrile (CAS Reg. No. 185982-80 -3) and the corresponding 3-endo isomer (CAS Reg. No. 185984-60-5) (see WO-96/37494, WO-98/25923),
and preparations containing insecticidal plant extracts, nematodes, fungi or viruses.

Also a mixture with other known active substances, such as herbicides or with fertilizers and growth regulators, safeners or semiochemicals is possible.

Furthermore have the compounds of the invention the formula (I) also very good antifungal effects. she have a very broad antimycotic spectrum of action, in particular against dermatophytes and yeasts, mold and diphasic fungi (e.g., against Candida species such as Candida albicans, Candida glabrata) and Epidermophyton floccosum, Aspergillus species such as Aspergillus niger and Aspergillus fumigatus, Trichophyton species such as Trichophyton mentagrophytes, Microsporon species such as Microsporon canis and audouinii. The list this mushroom does not under any circumstances limit the detectable mycotic Spectrum, but has only explanatory character.

The Active ingredients can as such, in the form of their formulations or the ones prepared from them Application forms, such as ready-to-use solutions, suspensions, wettable powders, Pastes, soluble Powder, dusts and granules are applied. The application happens in usual Way, e.g. by pouring, squirting, spraying, Scattering, dusting, foaming, Brushing, etc. It is also possible to deploy the active ingredients according to the ultra-low-volume method or the Drug preparation or to inject the drug itself into the soil. It can also be the seed of the plants to be treated.

At the Use of the active compounds according to the invention as fungicides can the application rates depending on the type of application within a larger area be varied. In the treatment of plant parts are the Application rates of active ingredient generally between 0.1 and 10,000 g / ha, preferably between 10 and 1,000 g / ha. In the seed treatment the application rates of active ingredient are generally between 0.001 and 50 grams per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed. When treating the soil are the Application rates of active ingredient generally between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g / ha.

As already mentioned above, can According to the invention, all plants and their parts are treated. In a preferred embodiment are wild or by conventional biological breeding methods, such as crossing or protoplast fusion obtained plant species and Treated plant varieties and their parts. In a further preferred embodiment are transgenic plants and plant varieties produced by genetic engineering Methods if necessary in combination with conventional methods were obtained (Genetically Modified Organisms) and their parts treated. The term "parts" or "parts of plants "or" plant parts "has been explained above.

Especially plants according to the invention are preferred the respective commercial or plant varieties in use. Among plant varieties one understands plants with new characteristics ("Traits"), which by both conventional breeding, by mutagenesis or by recombinant DNA techniques are. This can Be varieties, breeds, biotypes and genotypes.

ever according to plant species or plant varieties, their location and growth conditions (Floors, Climate, vegetation period, nutrition) can by the treatment according to the invention also superadditives ("Synergistic") effects occur. For example, reduced application rates and / or expansions of the Spectrum of action and / or an increase in the effect of the invention can be used Substances and agents, better plant growth, increased tolerance across from high or low temperatures, increased tolerance to dryness or against water or soil salt content, increased flowering efficiency, easier harvest, Acceleration of maturity, higher Crop yields, higher quality and / or higher Nutritional value of Harvested products, higher Shelf life and / or workability of the harvested products possible, beyond the actually expected Go beyond effects.

The preferred plants or plant cultivars to be treated according to the invention include all plants which have obtained genetic material by the genetic engineering modification which gives these plants particularly advantageous valuable properties ("traits") Examples of such properties are better plant growth. increased tolerance to high or low temperatures, increased tolerance to dryness or to bottoms, increased flowering efficiency, easier harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or machinability Further and particularly emphasized examples of such properties are an increased defense of the plants against animal and microbial pests, such as insects, mites, phytopathogenic fungi, bacteria and / or viruses as well as an increased tolerance of the plants against certain herbicidal active substances. Examples of transgenic plants include the important crops such as cereals (wheat, rice), corn, soybean, potato, cotton, tobacco, oilseed rape and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with corn, soybean, potato , Cotton, tobacco and oilseed rape. Traits which are particularly emphasized are the increased defense of the plants against insects, arachnids, namatodes and snails by toxins formed in the plants, in particular those which are produced by the genetic material from Bacillus thuringiensis (for example by the genes CryIA (a) , CryIA (b), CryIA (c), CryIIA, CryIIIA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CryIF and their combinations) in the plants (hereinafter "Bt plants"). Traits also become particularly emphasized is the increased defense of plants against fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins. Traits that are further emphasized are the increased tolerance of the plants to certain herbicidal active substances, for example Imi dazolinones, sulfonylureas, glyphosate or phosphinotricin (eg "PAT" gene). Each having the desired properties ( "traits") conferring genes can occur together in the transgenic plants in combination. Examples of "Bt plants" are maize varieties, cotton varieties, soya bean varieties and potato varieties may be mentioned that corn under the trade names YIELD GARD ^® (eg , cotton, soybeans), KnockOut ^® (for example maize), StarLink ^® (for example maize), Bollgard ^® (cotton), Nucoton ^® (cotton) and NewLeaf ^® (potato). Examples of herbicide-tolerant plants are maize varieties, cotton varieties called and soybean varieties are sold under the trade names Roundup Ready ^® (tolerance to glyphosate, for example maize, cotton, soya bean), Liberty link ^® (tolerance to phosphinotricin, for example oilseed rape), IMI ^® (tolerance to imidazolinones) and STS ^® (tolerance to sulphonylureas, for example As herbicide resistant (conventionally grown on herbicide tolerance) plants are also under the name Clearfield ^® represented mentioned varieties (eg maize). Of course, these statements also apply to future or future marketed plant varieties with these or future developed genetic traits.

The listed Plants can particularly advantageous according to the invention with the compounds of the general Treated formula (I) or the drug mixtures according to the invention become. The specified in the active ingredients or mixtures above Preferential ranges also apply to the treatment of these plants. Particularly emphasized is the Plant treatment with the compounds specifically listed herein or mixtures.

The Production and use of the active compounds according to the invention is based on following examples.

Production Examples Example 1

Method a)

To a solution of 1.201 g (5.518 mmol) of 4-ethoxy-3-methoxybenzylamine hydrochloride in 20 ml of dichloroethane and 1.117 g (11.035 mmol) of triethylamine is added at room temperature 1.285 g (5.061 mmol) of 3- (4-chlorophenyl) 5-methyl-4-isoxazole-carbonyl chloride and stirred for 1 hour under reflux. The mixture is cooled to room temperature, treated with 100 ml of ice water, acidified with conc. Acidified hydrochloric acid, mixed with dichloroethane, the organic phase separated, washed with water, dried over sodium sulfate and concentrated under reduced pressure. The residue is recrystallized from isopropanol. This gives 1.1 g (55% of theory) of N4- (4-ethoxy-3-methoxy-benzyl) -3- (4-chlorophenyl) -5-methylisoxazol-4-carboxamide of melting point 158 ° C.
HPLC: Log P = 2.93

Analogously to Example 1, as well as according to the general description of the preparation processes a) and b) according to the invention, the compounds of the formula (I) listed in Table 1 below can also be prepared:

Table 1

The determination of the logP values was carried out according to EEC Directive 79/831 Annex V. A ⁸ by HPLC (gradient method, acetonitrile / 0.1% aqueous phosphoric acid)

Preparation of the precursors of the formula (III) Example (III-a-1)

Method c)

To a solution of 4.1 g (21.620 mmol) of 4-hydroxy-3-methoxybenzylamine hydrochloride in 50 ml of ethyl acetate and 5 ml of triethylamine are added 4.954 g (22.7 mmol) of pyrocarbonic di-tert-butyl ester and stir 18 hours at room temperature. Subsequently, 100 ml of ethyl acetate are added to, washes with 50 ml of water then with 50 ml of dilute citric acid and 50 ml sodium bicarbonate solution and finally saturated with 50 ml Sodium chloride solution. The organic phase is over Dried sodium sulfate and concentrated under reduced pressure.

This gives 3.7 g (67% of theory) of tert-butyl 4-hydroxy-3-methoxybenzylcarbamate (VI-a * -1)
HPLC: log P = 1.91

To a solution of 3.7 g (14.607 mmol) of tert-butyl 4-hydroxy-3-methoxybenzylcarbamate (VI-a * -1) in 50 ml of acetone is added 5.43 g (36.519 mmol) of propargyl bromide, 5 g of anhydrous Added potassium carbonate and 0.15 g of potassium iodide and heated under reflux for 18 hours. The reaction mixture is added to 100 ml of water and extracted with 200 ml of ether. The organic phase is washed twice with 10% sodium hydroxide solution, dried over sodium sulfate and concentrated. This gives 3.2 g (73% of theory) of tert-butyl 4- (propargyloxy) -3-methoxybenzylcarbamate (III-a * -1).
(HPLC: log P = 2.57).

To a solution of 3.2 g (10.984 mmol) of tert-butyl 4- (propargyloxy) -3-methoxybenzylcarbamate in 50 ml of ethyl acetate are added 3 ml of conc. Hydrogen chloride solution, stirred for 18 hours at room temperature and filtered from the resulting precipitate. This is washed twice with ethyl acetate and dried in vacuo. 2.0 g (79% of theory) of 4- (propargyloxy) -3-methoxybenzylamine hydrochloride (III-a-1) are obtained.
(HPLC: log P = 0.20).

Analogously, and according to the general description of the preparation process c) according to the invention, the compounds of the formula (III) listed in Table 2 below can also be prepared:

Table 2

The determination of the logP values was carried out according to EEC Directive 79/831 Annex V. A ⁸ by HPLC (Gra dient method, acetonitrile / 0.1% aqueous phosphoric acid) Use examples: Example A Phytophthora test (tomato) / protective Solvent: 24.5 parts by weight of acetone 24.5 parts by weight of dimethylacetamide emulsifier: 1 part by weight of alkyl-aryl-polyglycol ether

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

to exam Protective effectiveness of young plants with the preparation of active ingredient sprayed in the specified rate. After the spray coating has dried on are the plants with an aqueous Spore suspension of Phytophthora infestans inoculated. The plants are then incubated in an incubation cabin at about 20 ° C and 100 relative humidity.

3 Days after the inoculation the evaluation takes place. This means 0% an efficiency equal to that of the control while a Efficiency of 100% means that no infestation is observed.

In this test, the inventive substances listed in Examples (1, 24, 38, 39, 40, 41, 42, 46, 47, 48, 50, 51, 54, 58, 61, 62, 68) at an application rate of 100 g / ha an efficiency of 94% or more. Example B Plasmopara test (vine) / protective Solvent: 24.5 parts by weight of acetone 24.5 parts by weight of dimethylacetamide emulsifier: 1 part by weight of alkyl-aryl-polyglycol ether

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

to exam Protective effectiveness of young plants with the preparation of active ingredient sprayed in the specified rate. After the spray coating has dried on are the plants with an aqueous Spore suspension of Plasmopara viticola inoculated and remain then 1 day in an incubation cabin at about 20 ° C and 100% relative humidity. Subsequently the plants are kept in the greenhouse for 4 days at approx. 21 ° C and approx. 90% humidity installed. The plants are then moistened and put in an incubation cabin for 1 day.

6 Days after the inoculation the evaluation takes place. This means 0% an efficiency equal to that of the control while a Efficiency of 100% means that no infestation is observed.

at This test shows that in the examples (1, 24, 35, 36, 38, 39, 40, 41, 42, 43, 44, 46, 47, 48, 49, 50, 51, 54, 56, 58, 61, 62, 68) Inventive substances at an application rate of 100 g / ha an efficiency of 90% or more.

Claims (7)

Amides of the formula (I)

in which R ¹ , R ² and R ^{3 are} identical or different and independently of one another represent hydrogen, halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl having in each case 1 to 8 carbon atoms; in each case straight-chain or branched alkenyl, alkynyl, alkenyloxy or alkynyloxy having in each case 2 to 6 carbon atoms; in each case straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms; in each case straight-chain or branched haloalkenyl or haloalkenyloxy having in each case 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms; in each case straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, hydroximinoalkyl or alkoximinoalkyl having in each case 1 to 6 carbon atoms in the individual alkyl moieties; Cycloalkyl having 3 to 6 carbon atoms, wherein R ¹ , R ² , and R ^{3 are} not simultaneously hydrogen, or R ¹ and R ² together with the carbon atoms to which they are attached, form a carbocyclic ring, Het an unsubstituted or substituted five-membered aromatic heterocyclic ring, R ^{4 is} hydrogen, halogen, cyano, alkyl of 1 to 8 carbon atoms, alkenyl or alkynyl of 2 to 8 carbon atoms or haloalkyl of 1 to 8 carbon atoms and 1 to 9 halogen atoms, R ⁵ and R ^{6 are the} same or different and are each independently unsubstituted or substituted by halogen or cyano alkyl, alkoxyalkyl each having 1-8 carbon atoms in the respective alkyl chains or alkenyl or alkynyl each having 2-8 carbon atoms or cycloalkyl having 3-8 carbon atoms or unsubstituted or substituted arylalkyl having 1-8 carbon atoms in the alkyl chain, A f r alkanediyl or cycloalkanediyl, and Y represents oxygen or sulfur. Process for the preparation of amides of the formula (I), where a) carboxylic acid derivatives of the general formula (II)

in which R ¹ , R ² , R ³ and R ^{4 have} the meanings given in the formula (I) in claim 1 and T is hydroxyl, halogen or alkoxy, with an amine of the general formula (III)

in which R ⁵ , R ⁶ and A have the meanings given in the formula (I) in claim 1, - or with an acid addition complex thereof - optionally in the presence of an acid acceptor, if appropriate in the presence of a condensing agent, optionally in the presence of a catalyst and optionally in Presence of a diluent, reacted and b) if appropriate (if Y in the formula (I) is S) with a sulfurizing reagent, if appropriate in the presence of a diluent. Means to combat of unwanted Microorganisms characterized by a content of at least an amide of formula (I) according to claim 1 in addition to extenders and / or surfactants. Use of amides of the formula (I) according to claim 1 to combat of unwanted Microorganisms. Method of control of unwanted Microorganisms, characterized in that amides of the formula (I) according to claim 1 on the unwanted Microorganisms and / or their habitat. Process for the preparation of compositions for controlling undesirable Microorganisms, characterized in that amides of the formula (I) according to claim 1 mixed with extenders and / or surfactants. Amines of the formulas

in which A and R ^{5 have} the meanings given in formula (I) in claim 1 and R ^{8 is} allyl, propargyl, 2-butynyl or cyanomethyl and (III-b)

in which A and R ^{6 have} the meanings given in formula (I) in claim 1 and R ^{9 is} allyl, propargyl, 2-butynyl or cyanomethyl.