DE19629465A1 - New alkyl glyoxylic acid amide derivatives - Google Patents

Abstract

Alkyl glyoxylic acid amide derivatives of formula (I) are new: A = single bond or optionally substituted alkylene; Q = O or S; R1 = a group of formula (a) or (b); G1,G2 = single bond, alkandiyl, alkendiyl, O, S, NH, N(alkyl) or carbonyl; G3,G4 = N or -C(Y8)=; Y1-Y8 = H, halo, cyano, nitro, or (each optionally substituted) alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkylsulphinyl, alkylsulphonyl or cycloalkyl; R2 = hydroxy, amino, or (each optionally substituted) alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylamino, dialkylamino, arylamino, cycloalkyl, cycloalkenyl, cycloalkoxy, cycloalkenyloxy, cycloalkylamino, aryl, arylalkyl, arylalkoxy or heterocyclyl; or a group -O-C(=Q1)-R5, -O-C(=Q1)-Q2-R6, -O-C(=Q1)-NR7R8, -O-SO2-R9, -NH-C(=Q1)-R5, -NH-C(Q1)-Q2-R6, -NH-C(=Q1)-NR7R8, or -NH-SO2-R9; Q1,Q2 = O or S; R5, R7 = H or optionally substituted alkyl or aryl; R6, R8 = optionally substituted alkyl or aryl; or NR7R8 = a heterocyclic ring (optionally alkyl substituted); R9 = alkyl, dialkylamino, N-bonded saturated heterocyclyl or aryl; R3 = H or (each optionally substituted) alkyl, alkenyl, alkynyl or cycloalkyl; R4 = (each optionally substituted) cycloalkyl, cycloalkenyl, aryl or heterocyclyl.

Description

The invention relates to new arylglyoxylic acid amides, a process for their preparation and their use as pesticides.

New compounds of the general formula (I) have been found

in which
A represents a single bond or optionally substituted alkylene,
Q represents oxygen or sulfur,
R¹ for a tricyclic

stands in what
G¹ and G² independently represent a single bond, alkanediyl, alkenediyl, oxygen, sulfur, -NH-, -N (alkyl) - or carbonyl,
G³ and G⁴ independently for nitrogen or a group

stand and
Y¹, Y², Y³, Y⁴, Y⁵, Y⁶, Y⁷ and Y⁸ independently represent hydrogen, halogen, cyano, nitro, each optionally substituted alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkylsulfinyl, alkylsulfonyl or cycloalkyl, or
R² is hydroxy, amino or optionally substituted alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylamino, dialkylamino, arylamino, cycloalkyl, cycloalkenyl, cycloalkoxy, cycloalkenyloxy, cycloalkylamino, aryl, arylalkyl, arylalkoxy or heterocyclyl or one of the following Groupings stands:

wherein
Q¹ and Q² independently of one another represent oxygen or sulfur,
R⁵ represents hydrogen or optionally substituted alkyl or aryl,
R⁶ represents optionally substituted alkyl or aryl,
R⁷ represents hydrogen or optionally substituted alkyl or aryl,
R⁸ represents optionally substituted alkyl or aryl, or
R⁷ and R⁸ together with the nitrogen atom to which they are attached represent an optionally substituted alkyl heterocyclic ring,
R⁹ represents optionally substituted alkyl, dialkylamino, saturated heterocyclyl or aryl bonded via nitrogen,
R³ represents hydrogen or in each case optionally substituted alkyl, alkenyl, alkynyl or cycloalkyl,
R⁴ stands for optionally substituted cycloalkyl, cycloalkenyl, aryl or heterocyclyl.

In the definitions are the saturated or unsaturated hydrocarbon chains, such as alkyl, alkanediyl, alkenyl or alkynyl, also in combination with heteroatoms, as in alkoxy, alkylthio or alkylamino, in each case straight-chain or branched.

Halogen generally represents fluorine, chlorine, bromine or iodine, preferably Fluorine, chlorine or bromine, especially for fluorine or chlorine.

Aryl stands for aromatic, mono- or polycyclic hydrocarbon rings, such as e.g. B. phenyl, naphthyl, anthranyl, phenanthryl, preferably phenyl or naphthyl, especially phenyl.

Heterocyclyl stands for saturated or unsaturated, as well as aromatic, ring-shaped Compounds in which at least one ring member has a heteroatom, i.e. H. one of Carbon is different atom. If the ring contains several heteroatoms, you can these be the same or different. Heteroatoms are preferably oxygen, nitrogen or sulfur.

Ring-shaped compounds optionally form with other carbocyclic or heterocyclic, fused or bridged rings together polycyclic ring system. Mono- or bicyclic ring systems are preferred, in particular mono- or bicyclic, aromatic ring systems.

Cycloalkyl stands for saturated, carbocyclic, ring-shaped compounds which optionally with other carbocyclic, fused or bridged Rings form a polycyclic ring system.

Cycloalkenyl stands for carbocyclic, ring-shaped compounds which have at least one Contain double bond and optionally with other carbocyclic, fused or bridged rings form a polycyclic ring system.

Finally it was found that the new arylglyoxylic acid amides of the general Formula (I) show very strong fungicidal activity.

The compounds according to the invention are optionally in the form of mixtures various possible isomeric forms, especially stereoisomers, such as. B. E and Z, threo and erythro and optical isomers before. It will be both the E and the Z isomers, as well as the threo- and erythro- as well as the optical Isomers and any mixtures of these isomers described and claimed.  

The invention preferably relates to compounds of the formula (I) in which
A represents a single bond or optionally mono- or polysubstituted, identical or differently substituted alkylene having 1 to 6 carbon atoms, the possible substituents preferably being selected from the list below:
Halogen, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl;
each straight-chain or branched, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms;
each straight-chain or branched alkenyl or alkenyloxy each having 2 to 6 carbon atoms;
each straight-chain or branched, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl, each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
each straight-chain or branched haloalkenyl or haloalkenyloxy each having 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
each straight-chain or branched alkylamino, dialkylamino, alkylcarb onyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydroximinoalkyl or alkoximinoalkyl each having 1 to 6 carbon atoms in the individual alkyl parts;
Cycloalkyl of 3 to 6 carbon atoms;
and in each case, if appropriate, once or several times, identically or differently
Halogen, cyano and / or straight-chain or branched alkyl having 1 to 4 carbon atoms
and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms
and / or straight-chain or branched alkoxy or alkylthio with 1 to 4 carbon atoms
and / or straight-chain or branched haloalkoxy or haloalkylthio having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms
and / or optionally one or more times, identical or different, by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms
and / or straight-chain or branched haloalkyl with 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms substituted, in each case doubly linked alkylene or dioxyalkylene, each with 1 to 6 carbon atoms, substituted aryl or heterocyclyl,
Q represents oxygen or sulfur,
R¹ for a tricyclic

stands in what
G¹ and G² independently represent a single bond, alkanediyl, alkenediyl, oxygen, sulfur, -NH-, -N (alkyl) - or carbonyl,
G³ and G⁴ independently for nitrogen or a group

stand and
Y¹, Y², Y³, Y⁴, Y⁵, Y⁶, Y⁷ and Y⁸ independently of one another for hydrogen, halogen, cyano, nitro;
Alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 8 carbon atoms in the individual alkyl parts;
Haloalkyl, haloalkoxy, haloalkylthio, haloalkyl sulfinyl or haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms or
Cycloalkyl having 3 to 6 carbon atoms,
R² is hydroxyl, amino or alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylamino, dialkylamino each having 1 to 4 carbon atoms in the respective alkyl parts, each optionally substituted by halogen, cyano or C₁-C₄alkoxy, each optionally by halogen, Cyano or C₁-C₄alkoxy substituted cycloalkyl, cycloalkenyl, cycloalkoxy, cyclo alkenyloxy, cycloalkylamino, with 3 to 8 carbon atoms in the respective rings or optionally substituted phenyl, benzyl, benzyloxy, naphthyl, phenylamino or heterocyclyl with 3 to 8 ring members, the possible substituents are preferably selected from the list below:
Halogen, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl, thio carbamoyl;
in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms;
each straight-chain or branched alkenyl or alkenyloxy each having 2 to 6 carbon atoms;
each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
each straight-chain or branched haloalkenyl or haloalkenyloxy each having 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
each straight-chain or branched alkylamino, dialkylamino, alkyl carbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydroximino alkyl or alkoximinoalkyl each having 1 to 6 carbon atoms in the individual alkyl parts;
each optionally mono- or polysubstituted, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, in each case doubly linked alkylene or dioxyalkylene each having 1 to 6 carbon atoms;
Cycloalkyl with 3 to 6 carbon atoms, or
R² represents one of the following groups:

wherein
Q¹ and Q² independently of one another represent oxygen or sulfur,
R⁵ stands for hydrogen or alkyl with 1 to 6 carbon atoms or for aryl or arylalkyl with 1 to 4 carbon atoms in the alkyl part which is optionally substituted in the aryl part by halogen, cyano, nitro, alkyl or alkoxy with 1 to 4 carbon atoms,
R⁶ represents alkyl with 1 to 6 carbon atoms or for aryl or arylalkyl with 1 to 4 carbon atoms in the alkyl part which is optionally substituted in the aryl part by halogen, cyano, nitro, alkyl or alkoxy with 1 to 4 carbon atoms,
R⁷ stands for hydrogen, alkyl with 1 to 6 carbon atoms or for ar in the aryl part optionally substituted by halogen, cyano, nitro, alkyl or alkoxy each with 1 to 4 carbon atoms substituted aryl or arylalkyl with 1 to 4 carbon atoms in the alkyl part,
R⁸ stands for alkyl with 1 to 6 carbon atoms or for aryl or arylalkyl with 1 to 4 carbon atoms in the alkyl part which is optionally substituted in the aryl part by halogen, cyano, nitro, alkyl or alkoxy with 1 to 4 carbon atoms, or
R⁷ and R⁸ together with the nitrogen atom to which they are attached represent an optionally substituted by methyl, heterocyclic ring,
R⁹ for alkyl having 1 to 6 carbon atoms, dialkylamino each having 1 to 4 carbon atoms in the individual alkyl parts, over nitrogen bound heterocyclyl with 3 to 7 ring members or for each given in the aryl part by halogen, cyano, nitro, alkyl or alkoxy with each 1 to 4 carbon atoms substituted aryl or arylalkyl having 1 to 4 carbon atoms in the alkyl part,
R³ represents hydrogen or alkyl having 1 to 4 carbon atoms,
R⁴ represents aryl, cycloalkyl or cycloalkenyl with 3 to 8 carbon atoms or heterocyclyl with 3 to 12 ring members, which are optionally mono- or polysubstituted by identical or different substituents, the possible substituents preferably being selected from the list below:
Halogen, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl;
in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms;
each straight-chain or branched alkenyl or alkenyloxy each having 2 to 6 carbon atoms;
each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
each straight-chain or branched haloalkenyl or haloalkenyloxy each having 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
each straight-chain or branched alkylamino, dialkylamino, alkyl carbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydroximino alkyl or alkoximinoalkyl each having 1 to 6 carbon atoms in the individual alkyl parts;
each optionally mono- or polysubstituted, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, in each case doubly linked alkylene or dioxyalkylene each having 1 to 6 carbon atoms;
Cycloalkyl of 3 to 6 carbon atoms;
and in each case, if appropriate, once or several times, identically or differently
Halogen, cyano and / or straight-chain or branched alkyl having 1 to 4 carbon atoms
and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms
and / or straight-chain or branched alkoxy or alkylthio with 1 to 4 carbon atoms
and / or straight-chain or branched haloalkoxy or haloalkylthio having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms
and / or optionally mono- or polysubstituted, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, each substituted twice linked alkylene or dioxyalkylene each having 1 to 6 carbon atoms,
substituted aryl, aryloxy, arylthio, arylalkyl, arylalkyloxy, arylalkylthio, heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylalkyl, heterocyclylalkyloxy or heterocyclylalkylthio.

The invention relates in particular to compounds of the formula (I) in which
A for a single bond or for in each case optionally single or multiple, identical or different methylene, 1,1-ethylene, 1,2-ethylene 1,1-, 1,2-, 1,3 substituted by fluorine, chlorine, cyano or methoxy - or 2,2-propylene, 1,1-, 1,2- 1,3-, 1,4-, 2,2-, 2,3-butylene or 1,1-, 1,2- or 1, 3- (2-methyl-propylene) stands,
Q represents oxygen or sulfur,
R¹ for a tricyclic

stands in what
G¹ and G² independently represent a single bond, alkanediyl, alkenediyl, oxygen, sulfur, -NH-, -N (alkyl) - or carbonyl and
G³ and G⁴ independently for nitrogen or a group

stand and
Y¹, Y², Y³, Y⁴, Y⁵, Y⁶, Y⁷ and Y⁸ independently of one another for 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 ethyl sulfonyl, trifluoromethyl, Trifluorethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, methylamino, ethylamino, nyl, iodomino, nyl, dimethyl
R² for hydroxy, amino or in each case optionally substituted by halogen, cyano, methoxy or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, vinyl, allyl, propargyl, methoxy, ethoxy , Allyloxy, propargyloxy, methylamino, ethylamino, dimethylamino, in each case optionally substituted by halogen, cyano, methoxy or ethoxy, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentyloxy, cyclohexyloxy, cyclopentylamino, cyclohexylamino or in each case optionally substituted phenyl, benzylhino, benzyl, benzyl, benzyl, benzyl, benzyl, benzyl, benzyl, benzyl, benzyl, benzyl, benzyl or heterocyclyl with 3 to 8 ring members, the possible substituents preferably being selected from the list below:
Fluorine, chlorine, bromine, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluorethoxy, dififluoromethylfluoromethylfluoromethylfluoromethylfluoromethylfluoromethyl , n- or i-propylamino, dimethylamino, diethyl amino, acetyl, propionyl, acetyloxy, methoxycarbonyl, ethoxycarbonyl, methylsulfonyloxy, ethylsulfonyloxy, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl or ethoximinoethyl,
each optionally mono- or polysubstituted, identically or differently, by fluorine, chlorine, methyl, trifluoromethyl, ethyl, n- or i-propyl, in each case doubly linked trimethylene (propane-1,3-diyl), tetramethylene (butane-1,4- diyl), methylenedioxy or ethylenedioxy,
Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, or
R² represents one of the following groups:

wherein
Q¹ and Q² independently of one another represent oxygen or sulfur,
R⁵ for hydrogen or methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or for each optionally in the phenyl part by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy or ethoxy-substituted phenyl, benzyl, 1-phenylethyl or 2-phenylethyl,
R⁶ for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or for each optionally in the phenyl part by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i Propyl, n-, i-, s- or t-butyl, methoxy or ethoxy substituted phenyl, benzyl, 1-phenylethyl or 2-phenylethyl,
R⁷ for hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or for each optionally in the phenyl part by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy or ethoxy-substituted phenyl, benzyl, 1-phenylethyl or 2-phenylethyl,
R⁸ for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or for each optionally in the phenyl part by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i Propyl, n-, i-, s- or t-butyl, methoxy or ethoxy-substituted phenyl, benzyl, 1-phenylethyl or 2-phenylethyl, or
R⁷ and R⁸ together with the nitrogen atom to which they are attached represent an optionally substituted by methyl, heterocyclic ring,
R⁹ for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, dimethylamino, diethylamino, pyrrolidin-1-yl, morpholin-N-yl, piperidin-1-yl or for each phenyl, benzyl, 1-phenylethyl or optionally substituted in the phenyl part by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy or ethoxy 2-phenylethyl is,
R³ represents hydrogen or methyl or ethyl,
R⁴ for in each case monosubstituted to trisubstituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, phenyl, naphthyl, furyl, benzofuranyl, pyrrolyl, indolyl, thienyl, benzothienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, pyridimidylolyl, pyridylzylyl, thiadiazolyl, thiadiazolyl, pyridylolyl, Pyridazinyl, pyrazinyl, oxiranyl, oxetanyl, tetrahydrofuryl, perhydropyranyl, pyrrolidinyl, piperidinyl or morpholinyl, where the possible substituents are preferably selected from the list below:
Fluorine, chlorine, bromine, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, chloromethoxy difluoro, trifluoroethoxy, difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl, methyl amino , Ethylamino, n- or i-propylamino, dimethylamino, diethylamino, acetyl, propionyl, acetyloxy, methoxycarbonyl, ethoxycarbonyl, methyl sulfonyloxy, ethylsulfonyloxy, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl or ethoximinoethyl
each optionally mono- or polysubstituted, identically or differently, by fluorine, chlorine, methyl, trifluoromethyl, ethyl, n- or i-propyl, in each case doubly linked trimethylene (propane-1,3-diyl), tetramethylene (butane-1,4- diyl), methylenedioxy or ethylenedioxy,
Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.

Compounds of the formula (I) in which
A for a single bond or for optionally single or multiple, identical or different, methylene, 1,1-ethylene, 1,2-ethylene 1,1-, 1,2-, 1,3- substituted by fluorine, chlorine, cyano, methoxy or 2,2-propylene, 1,1-, 1,2-, 1,3-, 1,4-2,2-, 2,3-butylene or 1,1-, 1,2- or 1,3 - (2-methyl-propylene) stands,
Q represents oxygen or sulfur,
R¹ for a tricyclic

stands in what
Y¹, Y², Y³, Y⁴, Y⁵, Y⁶, Y⁷ and Y⁸ independently of one another for 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, methylamino, ethylamino, n- or i-propylamethyl, cycloamino, cycloamino, methylamyl, methylamino, cyclo
R² for hydroxy, amino, methyl, fluoromethyl, difluoromethyl, trifluoromethyl, cyanophenyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, vinyl, allyl, methoxy, fluoromethoxy, difluoromethoxy, difluorochloromethoxy, Trifluoromoxy, cyanomethoxy, ethoxy, allyloxy, methylamino, ethylamino, dimethylamino, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentyloxy, cyclohexyloxy, cyclopentylamino, cyclohexylamino or in each case optionally substituted phenyl, benzyl, benzylylylylyl, naphthynyl, naphthynyl, naphthyl Morpholin-N-yl, piperidin-1-yl, benzofuranyl, thienyl, benzothienyl, pyridyl, quinolyl, tetrahydrofuryl or perhydropyranyl, the possible substituents preferably being selected from the list below:
Fluorine, chlorine, bromine, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluorethoxy, diformifluoromethylthio, diformifluoromethylthio, difluoromethylfluoromethyl, difluoromethylfluoromethyl, diformifluoromethylthio, difluoromethylfluoromethyl, Methylamino, ethylamino, n- or i-propylamino, dimethylamino, diethylamino, acetyl, propionyl, acetyloxy, methoxycarbonyl, ethoxycarbonyl, methylsulfonyloxy, ethylsulfonyloxy, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, ethoximinomethyl, methoxenominoethyl, or simply multiply Trimeth, each substituted by fluorine, chlorine, methyl, trifluoromethyl, ethyl, n- or i-propyl, is substituted twice ylene (propane-1,3-diyl), tetramethylene (butane-1,4-diyl), methylenedioxy or ethylenedioxy,
Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, or
R² represents one of the following groups:

wherein
Q¹ and Q² independently of one another represent oxygen or sulfur,
R⁵ for hydrogen or methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or for each optionally in the phenyl part by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy or ethoxy-substituted phenyl, benzyl, 1-phenylethyl or 2-phenylethyl,
R⁶ for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or for each optionally in the phenyl part by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i Propyl, n-, i-, s- or t-butyl, methoxy or ethoxy substituted phenyl, benzyl, 1-phenylethyl or 2-phenylethyl,
R⁷ for hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or for each optionally in the phenyl part by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy or ethoxy-substituted phenyl, benzyl, 1-phenylethyl or 2-phenylethyl,
R⁸ for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or for each optionally in the phenyl part by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i Propyl, n-, i-, s- or t-butyl, methoxy or ethoxy-substituted phenyl, benzyl, 1-phenylethyl or 2-phenylethyl, or
R⁷ and R⁸ together with the nitrogen atom to which they are attached represent an optionally substituted by methyl, heterocyclic ring,
R⁹ for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, dimethylamino, diethylamino, pyrrolidin-1-yl, morpholin-N-yl, piperidin-1-yl or for each phenyl, benzyl, 1-phenylethyl or optionally substituted in the phenyl part by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy or ethoxy 2-phenylethyl is,
R³ represents hydrogen or methyl,
R⁴ represents cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl which is optionally monosubstituted to six times, the preferred substituents being those mentioned below;
for in each case monosubstituted to trisubstituted phenyl, naphthyl, furyl, benzofuranyl, pyrrolyl, indolyl, thienyl, benzothienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridyl, quinolyl, pyrimidyl, oxidirylanyl, pyridaziryl, pyridaziryl, pyridazyryl, pyridazyryl, pyridazyryl, pyridazyryl, pyridazyryl, pyridazyryl, pyridazyryl, pyridazyryl, pyridazyryl, pyridazyryl, pyridazyryl, pyridazyryl, pyridazyryl, pyridazyryl, pyridazyryl, pyridazyryl, pyridazyryl, pyridazyryl, pyridazyryl, pyridazyryl, pyridazyryl, pyridazyryl , Perhydropyranyl, pyrrolidinyl, piperidinyl or morpholinyl, the possible substituents preferably being selected from the list below:
Fluorine, chlorine, bromine, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluorethoxy, diformifluoromethylthio, diformifluoromethylthio, difluoromethylfluoromethyl, difluoromethylfluoromethyl, diformifluoromethylthio, difluoromethylfluoromethyl, Methylamino, ethylamino, n- or i-propylamino, dimethylamino, diethylamino, acetyl, propionyl, acetyloxy, methoxycarbonyl, ethoxycarbonyl, methylsulfonyloxy, ethylsulfonyloxy, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, ethoximinomethyl, methoxenominoethyl, or simply multiply Trimeth, each substituted by fluorine, chlorine, methyl, trifluoromethyl, ethyl, n- or i-propyl, is substituted twice ylene (propane-1,3-diyl), tetramethylene (butane-1,4-diyl), methylenedioxy or ethylenedioxy,
Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.

A very particularly preferred group of compounds according to the invention are those compounds of the formula (I) in which
A represents a single bond or methylene, 1,1-ethylene, 1,2-ethylene, 1,1-propylene, 1,2-propylene, 1,3-propylene or 2,2-propylene,
Q represents oxygen,
R¹ for a tricyclic

stands in what
Y¹, Y², Y³, Y⁴, Y⁵, Y⁶, Y⁷ and Y⁸ independently of one another for 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, methylamino, ethylamino, n- or i-propylamyl, cyclo, methylamino, cyclo, methyl, cyclo, methyl, cyclo, methyl, cyclo, methyl, cyclo
R² represents one of the following groups:

wherein
Q¹ and Q² represent oxygen,
R⁵ for hydrogen or methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or for each optionally in the phenyl part by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy or ethoxy substituted phenyl, benzyl, 1-phenylethyl or 2-phenylethyl,
R⁶ for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or for each optionally in the phenyl part by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i Propyl, n-, i-, s- or t-butyl, methoxy or ethoxy substituted phenyl, benzyl, 1-phenylethyl or 2-phenylethyl,
R⁷ for hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or for each optionally in the phenyl part by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy or ethoxy substituted phenyl, benzyl, 1-phenylethyl or 2-phenylethyl,
R⁸ for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or for each optionally in the phenyl part by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i Propyl, n-, i-, s- or t-butyl, methoxy or ethoxy-substituted phenyl, benzyl, 1-phenylethyl or 2-phenylethyl, or
R⁷ and R⁸ together with the nitrogen atom to which they are attached represent an optionally substituted by methyl, heterocyclic ring,
R⁹ for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, dimethylamino, diethylamino, pyrrolidin-1-yl, morpholin-N-yl, piperidin-1-yl or for each phenyl, benzyl, 1-phenylethyl or optionally substituted in the phenyl part by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy or ethoxy 2-phenylethyl is,
R³ represents hydrogen or methyl,
R⁴ stands for cyclohexyl or optionally mono- to trisubstituted phenyl, thienyl, furyl, benzofuryl, benzothienyl, pyridyl, pyrimidinyl, naphthyl, quinolyl, the possible substituents preferably being selected from the list below:
Fluorine, chlorine, bromine, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, Difluorchlor methoxy, trifluoroethoxy, difluoromethylthio, difluorochloromethylthio, trifluoro-methylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl, methylamino , Ethylamino, n- or i-propylamino, dimethylamino, diethylamino, acetyl, propionyl, acetyloxy, methoxycarbonyl, ethoxycarbonyl, methylsulfonyloxy, ethylsulfonyloxy, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl or ethoximinoethyl
each optionally mono- or polysubstituted, identically or differently, by fluorine, chlorine, methyl, trifluoromethyl, ethyl, n- or i-propyl, in each case doubly linked trimethylene (propane-1,3-diyl), tetramethylene (butane-1,4- diyl), methylenedioxy or ethylenedioxy.

In particular, compounds of the formula (I) in which
R² is methoxy, fluoromethoxy, ethoxy, methylamino or dimethylamino.

In particular, compounds of the formula (I) in which
R³ represents hydrogen.

In particular, compounds of the formula (I) are preferred in which R⁴ for in 3- and 4-position is substituted by methoxy-substituted phenyl.

In a further particularly preferred group of compounds, A stands for -CH₂-CH₂-.

The radicals listed above or specified in preferred ranges definitions apply both to the end products of the formula (I) and correspondingly for the raw materials or intermediate products required for the production.

These residual definitions can be among themselves, that is, between the specified Areas of preferred connections, can be combined as desired.  

Furthermore, it was found that the new arylglyoxylic acid amides general formula (I) obtained when one

• a) carboxylic acid derivatives of the general formula (II) in which
  R¹, R² and Q have the meanings given above and
  T represents hydroxy, halogen or alkoxy,
  with an amine of the general formula (III) in which
  R³, R⁴ and A have the meanings given above,
  - or with a hydrogen halide thereof -
  if appropriate in the presence of an acid acceptor, if appropriate in the presence of a condensing agent and if appropriate in the presence of a diluent, or if
• b) glyoxylic acid amides of the general formula (IV) in which
  A, R¹, R², R³ and R⁴ have the meanings given above,
  with a sulfurization reagent, optionally in the presence of a diluent, or if
• c) glyoxylic acid derivatives of the formula (V) in which
  A, R¹, R³ and R⁴ have the meanings given above, and
  Z represents hydroxy or amino,
  with an activated acid derivative from one of the formulas (VI) to (XII), in which
  R⁵, R⁶, R⁷, R⁸ and R⁹ have the meanings given above,
  if appropriate in the presence of a diluent and if appropriate in the presence of a base.

Those used to carry out process a) as starting materials required carboxylic acid derivatives are generally defined by the formula (II). In of this formula (II) Q and R¹ preferably, or in particular those Meanings already in connection with the description of the inventions compounds of the formula (I) according to the invention are preferred or in particular be preferred for Q and R1; T preferably represents alkoxy with 1 to 4 Carbon atoms, especially for methoxy or ethoxy, for hydroxy or chlorine.

The starting materials of the formula (II) are known and / or per se known processes can be prepared (cf. EP-A 178 826, EP-A 242 081, EP-A 382 375, EP-A 493 711, EP-A 432 503, DE-A 39 38 054, J. Heterocycl. Chem. (1990), 27 (3), 487-95, Farmaco, Ed. Sci. (1980), 35 (5), 394-404, Justus Liebigs Ann. Chem. (1969), 722, 38-44, Justus Liebigs Ann. Chem. (1969), 722, 29-37, Tetrahedron 1971, 3431-6).

The further to carry out the method a) as The amines required as starting materials are generally defined by the formula (III). In this formula (III) R³, R⁴ and A preferably, or in particular those Meanings already related to the description of the Compounds of formula (I) according to the invention as preferred or as in particular were preferably given for R³, R⁴ and A.

The amines of the formula (III) are known organic synthetic chemicals and / or can be produced by methods known per se.

Those used to carry out process b) according to the invention as starting materials required glyoxylic acid amides are generally defined by the formula (IV). In this formula (IV) have A, R¹, R², R³ and R⁴ preferably or in particular those meanings that are already related to the description of the Compounds of formula (I) according to the invention as preferred or as in particular were preferably given for A, R¹, R², R³ and R⁴.

The glyoxylic acid amides of the general formula (IV) are ver bonds and can be obtained by the processes a) or c) according to the invention will.

As a sulfurization reagent for carrying out process b) according to the invention all reagents are possible that are able to bind to carbon  Exchange oxygen atoms for sulfur atoms, such as B. hydrogen sulfide, Phosphorus pentasulfide or Lawesson's reagent.

Those used to carry out process c) according to the invention as starting materials required glyoxylic acid derivatives are generally defined by the formula (V). In this formula (V) have A, R¹, R³ and R⁴ which preferably in particular those Meanings already in connection with the description of the inventions compounds of formula (I) according to the invention as preferred or as in particular were preferably given for A, R¹, R³ and R⁴. Z stands for hydroxy or amino.

The starting materials of the formula (V) are compounds according to the invention and can can be obtained by processes a) or b) according to the invention.

The continue to carry out the method c) according to the Preparation of the compounds of formula (I) according to the invention required Activated acid derivatives are generally defined by the formulas (VI) to (XII). In these formulas (VI) to (XII) preferably have R⁵, R⁶, R⁷, R⁸ and R⁹, or especially those meanings that are already related to the Description of the compounds of formula (I) according to the invention as preferred or as particularly preferred for R⁵, R⁶, R⁷, R⁸ and R⁹ have been specified.

The activated acid derivatives of the formulas (VI) to (XII) are known organic Synthetic chemicals and / or can be prepared by methods known per se will.

Process a) according to the invention is optionally carried out in the presence of a Diluent carried out. As a diluent to carry out the The method according to the invention includes water and organic solvents Consideration. These include in particular aliphatic, alicyclic or aromatic, optionally 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; Nitriles, like Acetonitrile, propionitrile or benzonitrile; Amines such as N, N-dimethylformamide, N, N- Dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphos phosphoric triamide; Esters such as methyl acetate or ethyl acetate, Sulfoxides, such as dimethyl sulfoxide, alcohols, such as methanol, ethanol, n- or i-Pro panol, ethylene glycol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether,  Diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, their mixtures with water or pure water.

Process a) according to the invention is optionally carried out in the presence of a suitable acid acceptor performed. As such come all the usual anorga African or organic bases in question. These include, for example, earth alkali metal or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, car bonates or bicarbonates, such as sodium hydride, sodium amide, Sodium methylate, sodium ethylate, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, amino nium acetate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate or ammonium carbonate, and also tertiary amines, such as trimethyl amine, triethylamine, tributylamine, N, N-dimethylaniline, N, N-dimethylbenzylamine, Pyridine, N-methylpiperidine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicycloundecene (DBU).

Process a) according to the invention is optionally carried out in the presence of a suitable condensing agent. As such, everyone usually comes condensing agents that can be used for such amidation reactions. 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 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) or triphenylphosphine / carbon tetrachloride.

Process a) according to the invention is optionally carried out in the presence of a catalyst sators performed. Examples include 4-dimethylaminopyridine, 1-Hy droxy-benzotriazole or dimethylformamide.

The reaction temperatures can be carried out when carrying out the process according to the invention Process a) can be varied over a wide range. Generally you work at temperatures between -20 ° C and + 200 ° C, preferably at temperatures between 0 ° C and 150 ° C.

To carry out process a) according to the invention, use is made per mole Carboxylic acid derivative of the formula (II) in general 1 to 5 mol, preferably 1.0 to 2.5 moles of amine.  

Carrying out the reaction, working up and isolating the reaction products takes place according to known methods (cf. the production examples).

Process a) according to the invention can also be carried out as a two-stage process will. The carboxylic acid derivatives of the general formula (II) are initially converted into an activated form and in a subsequent step with the amines of the general formula (III) for the alkoximinoacetic acid derivatives according to the invention th of the general formula (I) implemented.

All carboxy come as the activated form of the carboxylic acid derivatives of the formula (II) activated derivatives in question, such as B. acid halides, preferably acid chlorides, Acid azides, also symmetrical and mixed anhydrides, such as those mixed O-alkyl carbonic anhydrides, further activated esters, such as. B. p- Nitrophenyl ester or N-hydroxisuccinimide ester as well as adducts with condensation means such. B. dicyclohexylcarbodiimide or in situ generated activated forms of Carboxylic acids.

As a diluent for carrying out process b) according to the invention all inert organic solvents. These preferably include aliphatic, alicyclic or aromatic hydrocarbons, such as Pe trol ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or Decalin; halogenated hydrocarbons, such as chlorobenzene, dichloro benzene, 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 be carried out when carrying out the process according to the invention Process b) can be varied over a wide range. Generally you work at temperatures from 0 ° C to 150 ° C, preferably at temperatures from 0 ° C to 80 ° C.

To carry out the process b) according to the invention for producing the verbin The formula (I) is used per mole of the glyoxylic acid amide of the formula (IV) in generally 0.1 to 15 mol, preferably 0.5 to 8 mol, of a sulfurization reagent.

Coming as a diluent for carrying out process c) according to the invention all inert organic solvents. These preferably include aliphatic, alicyclic or aromatic hydrocarbons, such as Pe  trol ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or Decalin; halogenated hydrocarbons, such as chlorobenzene, dichloro benzene, 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; Ni triles such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile; Amides like N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methyl pyrrolidone or hexamethylphosphoric triamide; Esters such as methyl acetate or ethyl acetate; Sulfoxides such as dimethyl sulfoxide; or sulfones, like Sulfolan.

The process c) according to the invention is optionally in the presence of a suitable ten acid acceptor performed. All the usual inorganic ones come as such or organic bases in question. These preferably include alkaline earth metal or Alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hyd roe carbonates, such as sodium hydride, sodium amide, sodium methylate, Sodium ethylate, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, animoni umhydroxid, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, natri umcarbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate or ammonium carbonate, and also tertiary amines, such as trimethylamine, triethylamine, Tributylamine, N, N-dimethylaniline, N, N-dimethyl-benzylamine, pyridine, N-methyl pipe ridine, N-methylmorpholine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), Diazabicyclonones (DBN) or Diazabicycloundecen (DBU).

The reaction temperatures can be carried out when carrying out the process according to the invention Process c) can be varied over a wide range. Generally you work at temperatures from 0 ° C to 150 ° C, preferably at temperatures from 0 ° C to 80 ° C.

To carry out process c) according to the invention for the production of the verb of formula (I) are used per mole of the glyoxylic acid derivative of formula (V) generally 1 to 15 moles, preferably 2 to 8 moles of activated acid derivative one of the formulas (VI) to (XII).

The processes according to the invention are generally carried out under normal pressure guided. However, it is also possible, under increased or reduced pressure - im generally between 0.1 bar and 10 bar - to work.  

Carrying out the reaction, working up and isolating the reaction products takes place according to known methods (see also the production examples).

The active compounds according to the invention have a strong microbicidal action and can be used to combat unwanted microorganisms will. The active ingredients are for use as crop protection agents, in particular suitable as fungicides.

Fungicides in crop protection are used to combat plasmo diophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basi diomycetes, Deuteromycetes.

Bactericidal agents are used in plant protection to combat Pseudomonada ceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae used.

Some pathogens of fungal and bacterial diseases that fall under the generic names listed above may be mentioned as examples, but not by way of limitation:
Xanthomonas species, such as, for example, Xanthomonas campestris pv. Oryzae;
Pseudomonas species, such as, for example, Pseudomonas syringae pv. Lachrymans;
Erwinia species, such as, for example, Erwinia amylovora;
Pythium species, such as, for example, Pythium ultimum;
Phytophthora species, such as, for example, Phytophthora infestans;
Pseudoperonospora species, such as, for example, Pseudoperonospora humuli or Pseudoperonospora cubensis;
Plasmopara species, such as, for example, Plasmopara viticola;
Bremia species, such as, for example, Bremia lactucae;
Peronospora species, such as, for example, Peronospora pisi or P. brassicae;
Erysiphe species, such as, for example, Erysiphe graminis;
Sphaerotheca species, such as, for example, Sphaerotheca fuliginea;
Podosphaera species, such as, for example, Podosphaera leucotricha;
Venturia species, such as, for example, Venturia inaequalis;
Pyrenophora species, such as, for example, Pyrenophora teres or P. graminea (conidial form: Drechslera, Syn: Helminthosporium);
Cochliobolus species, such as, for example, Cochliobolus sativus (conidial form: Drechslera, Syn: Helminthosporium);
Uromyces species, such as, for example, Uromyces appendiculatus;
Puccinia species, such as, for example, Puccinia recondita;
Sclerotinia species, such as, for example, Sclerotinia sclerotiorum,
Tilletia species, such as, for example, Tilletia caries;
Ustilago species, such as, for example, Ustilago nuda or Ustilago avenae;
Pellicularia species, such as, for example, Pellicularia sasakii;
Pyricularia species, such as, for example, Pyricularia oryzae;

Fusarium species, such as, for example, Fusarium culmorum;
Botrytis species, such as, for example, Botrytis cinerea;
Septoria species, such as, for example, Septoria nodorum;
Leptosphaeria species, such as, for example, Leptosphaeria nodorum;
Cercospora species, such as, for example, Cercospora canescens;
Alternaria species, such as, for example, Altemaria brassicae;
Pseudocercosporella species, such as, for example, Pseudocercosporella herpotrichoides.

The good plant tolerance of the active ingredients in the control of plants Concentrations necessary for diseases allow treatment above ground Parts of plants, of seedlings, and of the soil.

The active compounds according to the invention are particularly successful Combating diseases in wine, fruit and vegetable growing, such as used against Plasmopara and Phytophthora species.

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

These formulations are prepared in a known manner, e.g. B. by mixing of the active ingredients are under pressure with extenders, i.e. liquid solvents the liquefied gases and / or solid carriers, if necessary with use formation of surface-active agents, i.e. emulsifiers and / or dispersants agents and / or foaming agents. In case of using water as Extenders can e.g. B. also ver organic solvents as auxiliary solvents be applied. The following are essentially suitable as liquid solvents: Aro mat, such as xylene, toluene or alkyl naphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride rid, aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. B. Petroleum Iraq ions, 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 solvents such as dimethylformamide and dimethyl sulfoxide, and water. With fuzzy Such gaseous extenders or carriers are such liquids meant which are gaseous at normal temperature and pressure, e.g. B. aerosol propellants, such as halogenated hydrocarbons and butane, propane, stick substance and carbon dioxide. As solid carriers come into question: B. natural Ge stone powders, such as kaolins, clays, talc, chalk, quartz, affapulgite, Montmorillo nit or diatomaceous earth and synthetic rock powder, such as finely divided pebbles acid, aluminum oxide and silicates. As solid carriers for granules come in Question: e.g. B. broken and fractionated natural rocks such as calcite, marble, Pumice, sepiolite, dolomite and synthetic granules from inorganic and orga African flours and granules made of organic material such as sawdust, coconut husks, corn cobs and tobacco stalks. As an emulsifier and / or foam generator Funds are possible: B. non-ionic and anionic emulsifiers, such as poly oxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. B. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates. As a dis Pouring agents are possible: B. lignin sulfite and methyl cellulose.

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

Dyes such as inorganic pigments, e.g. B. iron oxide, titanium oxide, Ferrocyan blue and organic dyes such as alizarin, azo and metal phthalalo cyanine dyes and trace nutrients, such as salts of iron, manganese, boron, copper, Cobalt, molybdenum and zinc can be used.

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

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

The following connections can be considered as mixed partners:

Fungicides

Aldimorph, ampropylfos, ampropylfos potassium, andoprim, anilazine, azaconazole, azoxystrobin,
Benalaxyl, benodanil, benomyl, benzamacril, benzamacrylic isobutyl, bialaphos, binapacrylic, biphenyl, bitertanol, blasticidin-S, bromuconazole, bupirimate, buthiobate,
Calcium polysulfide, capsimycin, captafol, captan, carbendazim, carboxin, carvone, quinomethionate (quinomethionate), chlobenthiazone, chlorfenazole, chloroneb, chloropicrin, chlorothalonil, chlozolinate, clozylacon, cufraneb, cymoxanil, cyphodaminazol, cypodaminazol, cypodinconol
Debacarb, dichlorophene, diclobutrazole, diclofluanide, diclomezin, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole, diniconazol-M, dinocap, diphenylamine, dipyrithione, ditalimfos, dithorphoxinodonine, dithorphononodine
Ediphenphos, Epoxiconazole, Etaconazole, Ethirimol, Etridiazole,
Famoxadone, fenapanil, fenarimol, fenbuconazole, fenfuram, fenitropan, fenpiclonil, fenpropidine, fenpropimorph, fentin acetate, fentin hydroxide, ferbam, ferimzon, fluazinam, flumetover, fluoromid, fluquinconazole, flurprimolol, fusilazolutol, fusilazolutolid, fusulfolazolutol, fusilazolutol, fusilazolutol, fusilazolutol, fusilazolutol, fusilazolutol, fusilazolutol, fusilazolutol, fusilazolutol, fusilazolutol, fusilazolutolol, fusilazolutolol, fusilazoletol, fusilazoletol, fusilazolutolol, fusilazoletol, fusilazoletol, fusilazoletol, fusilazoletol, fulosilazoletol Fosetyl sodium, fthalide, fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole, furconazole-cis, furmecyclox,
Guazatin,
Hexachlorobenzene, hexaconazole, hymexazole,
Imazalil, Imibenconazol, Iminoctadin, Iminoctadinealbesilate, Iminoctadinetriacetate, Iodocarb, Ipconazol, Iprobefos (IBP), Iprodione, Irumamycin, Isoprothiolan, Isovaledione,
Kasugamycin, Kresoxim-methyl, copper preparations, such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, oxine-copper and Bordeaux mixture,
Mancopper, Mancozeb, Maneb, Meferinizone, Mepanipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Methfuroxam, Metiram, Metomeclam, Metsulfovax, Mildiomycin, Myclobutanil, Myclozolin,
Nickel dimethyldithiocarbamate, nitrothal isopropyl, nuanmol,
Ofurace, Oxadixyl, Oxamocarb, Oxolimcacid, Oxycarboxim, Oxyfenthiin,
Paclobutrazole, Pefurazoate, Penconazole, Pencycuron, Phosdiphen, Pimaricm, Piperalin, Polyoxin, Polyoxonm, probenazole, Prochloraz, Procymidon, Propaniocarb, Propanosine-Sodium, Propiconazole, Propineb, Pyrazophos, Pyrifen, Pyifenox, Pyrroyilonil
Quinconazole, quintozen (PCNB),
Sulfur and sulfur preparations,
Tebuconazole, tecloftalam, tecnazene, Tetcyclacis, tetraconazole, thiabendazole, Thicyofen, Thifluzamide, thiophanate-methyl, thiram, Tioxymid, Toldclofos-methyl, tolylfluanid, triadimefon, triadimenol, Triazbutil, triazoxide, Trichlamid, tricyclazole, tridemorph, triflumizole, triforine, triticonazole,
Uniconazole,
Validamycin A, vinclozolin, viniconazole,
Zarilamid, Zineb, Ziram as well
Dagger G,
OK-8705,
OK-8801,
α- (1,1-dimethylethyl) -β- (2-phenoxyethyl) -1H-1,2,4-triazole-1-ethanol,
α- (2,4-dichlorophenyl) -β-fluoro-β-propyl-1H-1,2,4-triazole-1-ethanol,
α- (2,4-dichlorophenyl) -β-methoxy-α-methyl-1H-1,2,4-triazole-1-ethanol,
α- (5-methyl-1,3-dioxan-5-yl) -β - [[4- (trifluoromethyl) phenyl] methylene] -1H-1,2,4-triazol-1-ethanol,
(5RS, 6RS) -6-hydroxy-2,2,7,7-tetramethyl-5- (1H-1,2,4-triazol-1-yl) -3-octanone,
(E) -α- (methoxyimino) -N-methyl-2-phenoxy-phenylacetamide,
{2-Methyl-1 - [[[1- (4-methylphenyl) ethyl] amino] carbonyl] propyl} carbamic acid 1-isopropyl ester
1- (2,4-dichlorophenyl) -2- (1H-1,2,4-triazol-1-yl) ethanone-O- (phenylmeth-yl) oxime,
1- (2-methyl-1-naphthalenyl) -1H-pyrrole-2,5-dione,
1- (3,5-dichlorophenyl) -3- (2-propenyl) -2,5-pyrrolidinedione,
1 - [(diiodomethyl) sulfonyl] -4-methyl-benzene,
1 - [[2- (2,4-dichlorophenyl) -1,3-dioxolan-2-yl] methyl] -1H-imidazole,
1 - [[2- (4-chlorophenyl) -3-phenyloxiranyl] methyl] -1H-1,2,4-triazole,
1- [1- [2 - [(2,4-dichlorophenyl) methoxy] phenyl] ethenyl] -1H-imidazole,
1-methyl-5-nonyl-2- (phenylmethyl) -3-pyrrolidinol,
2 ′, 6′-dibromo-2-methyl-4′-trifluoromethoxy-4′-trifluoromethyl-1,3-thiazole-5-carboxanilide,
2,2-dichloro-N- [1- (4-chlorophenyl) ethyl] -1-ethyl-3-methyl-cyclopropanc-arboxamide,
2,6-dichloro-5- (methylthio) -4-pyrimidinyl-thiocyanate,
2,6-dichloro-N- (4-trifluoromethylbenzyl) benzamide,
2,6-dichloro-N - [[4- (trifluoromethyl) phenyl] methyl] benzamide,
2- (2,3,3-triiodo-2-propenyl) -2H-tetrazole,
2 - [(1-methylethyl) sulfonyl] -5- (trichloromethyl) -1,3,4-thiadiazole,
2 - [[6-Deoxy-4-O- (4-O-methyl-β-D-glycopyranosyl) -α-D-glucopyranosyl] amino] -4- methoxy-1H-pyrrolo [2,3-d] pyrimidine-5-carbonitrile,
2Aminobutane,
2-bromo-2- (bromomethyl) pentandinitrile,
2-chloro-N- (2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl) -3-pyridinecarboxamide,
2-chloro-N- (2,6-dimethylphenyl) -N- (isothiocyanatomethyl) acetamide,
2-phenylphenol (OPP),
3,4-dichloro-1- [4- (difluoromethoxy) phenyl] -1H-pyrrole-2,5-dione,
3,5-dichloro-N- [cyan [(1-methyl-2-propynyl) oxy] methyl] benzamide,
3- (1,1-dimethylpropyl-1-oxo-1H-indene-2-carbonitrile,
3- [2- (4-chlorophenyl) -5-ethoxy-3-isoxazolidinyl] pyridine,
4-chloro-2-cyan-N, N-dimethyl-5- (4-methylphenyl) -1H-imidazole-1-sulfona-mid,
4-methyl-tetrazolo [1,5-a] quinazolin-5 (4H) -one,
8- (1,1-dimethylethyl) -N-ethyl-N-propyl-1,4-dioxaspiro [4.5] decan-2-methanamine,
8-hydroxyquinoline sulfate,
9H-xanthene-9-carboxylic acid 2 - [(phenylamino) carbonyl] hydrazide,
bis- (1-methylethyl) -3-methyl-4 - [(3-methylbenzoyl) oxy] -2,5-thiophene di-carboxylate,
cis-1- (4-chlorophenyl) -2- (1H-1,2,4-triazol-1-yl) cycloheptanol,
cis-4- [3- [4- (1,1-dimethylpropyl) phenyl-2-methylprop yl] -2,6-dimethyl-morpholine hydrochloride,
Ethyl - [(4-chlorophenyl) azo] cyanoacetate,
Potassium hydrogen carbonate,
Methane tetrathiol, sodium salt,
Methyl 1- (2,3-dihydro-2,2-dimethyl-1H-inden-1-yl) -1H-imidazole-5-carboxylate,
Methyl N- (2,6-dimethylphenyl) -N- (5-isoxazolylcarbonyl) -DL-alaninate,
Methyl N- (chloroacetyl) -N- (2,6-dimethylphenyl) -DL-alaninate,
N- (2,3-dichloro-4-hydroxyphenyl) -1-methyl-cyclohexane carboxamide,
N- (2,6-dimethylphenyl) -2-methoxy-N- (tetrahydro-2-oxo-3-furanyl) acetamide,
N- (2,6-dimethylphenyl) -2-methoxy-N- (tetrahydro-2-oxo-3-thienyl) acetamide,
N- (2-chloro-4-nitrophenyl) -4-methyl-3-nitro-benzenesulfonamide,
N- (4-cyclohexylphenyl) -1,4,5,6-tetrahydro-2-pyrimidinamine,
N- (4-hexylphenyl) -1,4,5,6-tetrahydro-2-pyrimidinamine,
N- (5-chloro-2-methylphenyl) -2-methoxy-N- (2-oxo-3-oxazolidmyl) acetami-d,
N- (6-methoxy) -3-pyridinyl) cyclopropanecarboxamide,
N- [2,2,2-trichloro-1 - [(chloroacetyl) amino] ethyl] benzamide,
N- [3-chloro-4,5-bis (2-propynyloxy) phenyl] -N'-methoxy-methanimidamide, -
N-formyl-N-hydroxy-DL-alanine, sodium salt,
O, O-diethyl- [2- (dipropylamino) -2-oxoethyl] ethylphosphoramidothioat, -
O-methyl-S-phenyl-phenylpropylphosphoramidothioat,
S-methyl-1,2,3-benzothiadiazole-7-carbothioate,
spiro [2H] -1-benzopyran-2,1 ′ (3′H) -isobenzofuran] -3′-one,

Bactericides

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

Insecticides / acaricides / nematicides

Abamectin, Acephat, Acrinathrin, Alanycarb, Aldicarb, Alphamethrin, Amitraz, Avermectin, AZ 60541, Azadirachtin, Azinphos A, Azinphos M, Azocyclotin,
Bacillus thuringiensis, 4-Bromo-2- (4-chlorophenyl) -1- (ethoxymethyl) -5- (trifluoro methyl) -1H-pyrrole-3-carbonitrile, Bendiocarb, Benfuracarb, Bensultap, Betacyflu thrin, Bifenthrin, BPMC, Brofenprox , Bromophos A, Bufencarb, Buprofezin, Buto carboxin, Butylpyridaben,
Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, Chloetho carb, Chlorethoxyfos, Chlorfenvinphos, Chlorfluazuron, Chlormephos, N - [(6-Chloro- 3-pyridinyl) -methyl] -N'-cyano-N-methyl-ethanimidamide, Chlorpyrifos, Chlorpyrifos M, Cis-Resmethrin, Clocythrin, Clofentezin, Cyanophos, Cycloprothrin, Cyfluthrin, Cyhalothrin, Cyhexatin, Cypermethrin, Cyromazin,
Deltamethrin, Demeton M, Demeton S, Demeton-S-methyl, Diafenthiuron, Diazinon, Dichlofenthion, Dichlorvos, Dicliphos, Dicrotophos, Diethion, Diflubenzuron, Dime thoat,
Dimethylvinphos, dioxathione, disulfoton,
Edifenphos, Emamectin, Esfenvalerat, Ethiofencarb, Ethion, Ethofenprox, Ethopro phos, Etrimphos,

Fenamiphos, Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipronil, Fluazinam, Fluazuron, Flucycloxuron, Flucythrinat, Flufenxurophone, Flufenoxurion, Fufonxionfonofionfonofionfonofionfonofionfonofionfonofinfoxfonofionfonofoxfonofionfonofionfonofinfurofunofhrof, fufionphonofionphonofionfonofoxfonofionfurofunof, fufionphonofionfonofionfurofunofhrof, fufionphonofionfonofonfoxfonofonofonfoxofonofuronfoxofonofuronfoxfonofinfoxfos
HCH, heptenophos, hexaflumuron, hexythiazox,
Imidacloprid, iprobefos, isazophos, isofenphos, i 06710 00070 552 001000280000000200012000285910659900040 0002019629465 00004 06591soprocarb, isoxathione, ivermectin,
Lamda-cyhalothrin, Lufenuron,
Malathion, Mecarbam, Mervinphos, Mesulfenphos, Metaldehyde, Methacrifos, Metha midophos, Methidathion, Methiocarb, Methomyl, Metolcarb, Milbemectin, Mono crotophos, Moxidectin,
Naled, NC 184, Nitenpyram
Omethoate, Oxamyl, Oxydemethon M, Oxydeprofos,
Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet, Phos phamidon, Phoxim, Pirimicarb, Pirimiphos M, Pirimiphos A, Profenophos, Promecarb, Propaphos, Propoxur, Prothiophos, Prothoat, Pymetroion, Pyridaphrinophin, Pyridaphrinophin , Pyridaben, pyrimidifen, pyriproxifen,
Quinalphos,
Salithion, Sebufos, Silafluofen, Sulfotep, Sulprofos,
Tebufenozide, Tebufenpyrad, Tebupirimphos, Teflubenzuron, Tefluthrin, Temephos, Terbam, Terbufos, Tetrachlorvinphos, Thiafenox, Thiodicarb, Thiofanox, Thiome thon, Thionazin, Thuringiensin, Tralomenhrononium, Triaromenhriazonium, Tri
Vamidothione, XMC, xylylcarb, zetamethrin.

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

The active compounds according to the invention can be taken as such, in the form of their commercially available Formulations or the use forms prepared from them, such as ready-to-use Solutions, suspensions, wettable powders, pastes, soluble powders, dusts and Granules can be applied. The application is done in the usual way, e.g. B. by pouring, spraying, spraying, scattering, foaming, brushing, etc. It is also possible to use the active ingredients using the UItra low-volume process apply or the active ingredient preparation or the active ingredient itself in the soil to inject. The seeds of the plants can also be treated.

In the treatment of parts of plants, the drug concentrations in the Application forms can be varied in a larger area: They are in the generally between 1 and 0.0001% by weight, preferably between 0.5 and 0.001 % By weight.

In the seed treatment, amounts of active ingredient are generally from 0.001 to 50 g per kilogram of seed, preferably 0.01 to 10 g.  

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

Manufacturing examples example 1

To a solution of 3.22 g (10 mmol) of 2- (9,10-dihydroanthracen-2-yl) -2- Ethoximinoacetic acid ethyl ester in 50 ml of methanol is added in succession at 20 ° C. 1.81 g (10 mmol) of 2- (3,4-dimethoxyphenyl) ethylamine and 3.6 g (20 mmol) of 30% methanolic sodium methylate solution. The mixture is 20 hours at 20 ° C. stirred, then the solvent was distilled off. The backlog is in Methylene chloride added, first with water, then with dilute hydrochloric acid and again washed with water and dried over sodium sulfate. After The solvent is distilled off using petroleum ether / ethyl acetate (2: 1) on silica gel chromatographed.

1.3 g (28% of theory) of N- [2- (3,4-dimethoxyphenyl) ethyl] -2- (9,10-dihydroanthracen-2-yl) -2-ethoximino-acetamide are obtained as oil and as a mixture of stereoisomers.
HPLC: logP: 3.62 (e-isomer)
4.00 (z-isomer).

Analogously to Examples 1 and in accordance with the general description of the Manufacturing method according to the invention, for example, in the compounds listed in Table 1 below:

Table 1

Examples of use Example A Phytophthora test (tomato) / protective

Solvent: 47 parts by weight of acetone
Emulsifier: 3 parts by weight of alkylaryl polyglycol ether

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

To test for protective activity, young plants are added with the active ingredient preparation sprayed with dew. After the spray coating has dried on, the Plants with an aqueous spore suspension of Phytophthora infestans inoculated.

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

Evaluation is carried out 3 days after the inoculation. Here means a Efficiency of 0%, that the infection on the treated plants is that of the corresponds to untreated control, while an efficiency of 100% means that no infection is observed on the treated plants.

In this test, e.g. B. the compounds (2) and (3) of the preparation examples with an exemplary active ingredient application rate of 50 g / ha, an efficiency of 96% compared to the untreated control.  

Example B Plasmopara test (vines) / protective

Solvent: 47 parts by weight of acetone
Emulsifier: 3 parts by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, 1 Ge is mixed most of the active ingredient with the specified amounts of solvent and emulsifier and dilute the concentrate with water to the desired concentration.

To test for protective activity, young plants are added with the active ingredient preparation sprayed with dew. After the spray coating has dried on, the plants zen inoculated with an aqueous spore suspension of Plasmopara viticola and then remain in an incubation cabin for 1 day at approx. 20 ° C and 100% relative Humidity. The plants are then grown for 5 days in a greenhouse at approx. 21 ° C and approx. 90% humidity. The plants are then planted damp and placed in an incubation cabin for 1 day.

Evaluation is carried out 6 days after the inoculation. Here means a Efficiency of 0%, that the infection on the treated plants is that of the corresponds to untreated control, while an efficiency of 100% means that no infection is observed on the treated plants.

In this test, e.g. B. the compounds of preparation examples (2) and (3) with an exemplary active ingredient application rate of 50 g / ha, an efficiency of 96 to 100% compared to the untreated control.

Claims (9)

1. compounds of the general formula (I) found, in which
A represents a single bond or optionally substituted alkylene,
Q represents oxygen or sulfur,
R¹ for a tricyclic stands in what
G¹ and G¹ independently of one another represent a single bond, alkanediyl, alkenediyl, oxygen, sulfur, -NH-, -N (alkyl) - or carbonyl,
G³ and G⁴ independently for nitrogen or a group stand and
Y¹, Y², Y³, Y⁴, Y⁵, Y⁶, Y⁷ and Y⁸ are independently hydrogen, halogen, cyano, nitro, each optionally substituted alkyl, alkoxy, alkylamino, dialkyl amino, alkylthio, alkylsulfinyl, alkylsulfonyl or cycloalkyl, or
R² for hydroxy, amino or in each case optionally substituted alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkyl amino, dialkylamino, arylamino, cycloalkyl, cycloalkenyl, cycloalkoxy, cycloalkenyloxy, cycloalkylamino, aryl, arylalkyl, arylalkoxy or heterocyclyl or one of the the following groups: wherein
Q¹ and Q² independently of one another represent oxygen or sulfur,
R⁵ represents hydrogen or optionally substituted alkyl or aryl,
R⁶ represents optionally substituted alkyl or aryl,
R⁷ represents hydrogen or optionally substituted alkyl or aryl,
R⁸ represents optionally substituted alkyl or aryl, or
R⁷ and R⁸ together with the nitrogen atom to which they are attached represent an optionally substituted alkyl heterocyclic ring,
R⁹ represents optionally substituted alkyl, dialkylamino, saturated heterocyclyl or aryl bonded via nitrogen,
R³ represents hydrogen or in each case optionally substituted alkyl, alkenyl, alkynyl or cycloalkyl,
R⁴ stands for optionally substituted cycloalkyl, cycloalkenyl, aryl or heterocyclyl. 2. Compounds of formula (I) according to claim 1, in which
A stands for a single bond or for optionally mono- or polysubstituted, identical or differently substituted alkylene having 1 to 6 carbon atoms, the possible substituents being selected from the list below:
Halogen, cyano, nitro, amino, hydroxy, formyl, carboxy, carb amoyl, thiocarbamoyl;
each straight-chain or branched, alkoxy, alkylthio, alkyl sulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms;
each straight-chain or branched alkenyl or alkenyloxy each having 2 to 6 carbon atoms;
each straight-chain or branched, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
each straight-chain or branched haloalkenyl or haloalkenyloxy each having 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
each straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydroximinoalkyl or alkoximinoalkyl each having 1 to 6 carbon atoms in the individual alkyl parts;
Cycloalkyl of 3 to 6 carbon atoms;
as well as, if necessary, single or multiple, the same or different
Halogen, cyano and / or straight-chain or branched alkyl having 1 to 4 carbon atoms
and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms
and / or straight-chain or branched alkoxy or alkylthio with 1 to 4 carbon atoms
and / or straight-chain or branched haloalkoxy or haloalkylthio having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms
and / or optionally single or multiple, identical or different by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms
and / or straight-chain or branched haloalkyl with 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms substituted, in each case doubly linked alkylene or dioxyalkylene, each with 1 to 6 carbon atoms, substituted aryl or heterocyclyl,
Q represents oxygen or sulfur,
R¹ for a tricyclic stands in what
G¹ and G² independently represent a single bond, alkanediyl, alkenediyl, oxygen, sulfur, -NH-, -N (alkyl) - or carbonyl,
G³ and G⁴ independently for nitrogen or a group stand and
Y¹, Y², Y³, Y⁴, Y⁵, Y⁶, Y⁷ and Y⁸ independently of one another for hydrogen, halogen, cyano, nitro;
Alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 8 carbon atoms in the individual alkyl parts;
Haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms or
Cycloalkyl having 3 to 6 carbon atoms,
R² is hydroxyl, amino or alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylamino, dialkylamino each having 1 to 4 carbon atoms in the respective alkyl parts, each optionally substituted by halogen, cyano or C₁-C₄alkoxy, each optionally by halogen, Cyano or C₁-C₄alkoxy substituted cycloalkyl, cycloalkenyl, cycloalkoxy, cyclo alkenyloxy, cycloalkylamino, with 3 to 8 carbon atoms in the respective rings or optionally substituted phenyl, benzyl, benzyloxy, naphthyl, phenylamino or heterocyclyl with 3 to 8 ring members, the possible substituents are preferably selected from the list below:
Halogen, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl;
in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms;
each straight-chain or branched alkenyl or alkenyloxy each having 2 to 6 carbon atoms;
each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
each straight-chain or branched haloalkenyl or haloalkenyloxy each having 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
each straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydroximinoalkyl or alkoximinoalkyl each having 1 to 6 carbon atoms in the individual alkyl parts;
each optionally mono- or polysubstituted, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, each substituted twice linked alkylene or dioxy alkylene each having 1 to 6 carbon atoms;
Cycloalkyl with 3 to 6 carbon atoms, or
R² represents one of the following groups: wherein
Q¹ and Q² independently of one another represent oxygen or sulfur,
R⁵ stands for hydrogen or alkyl with 1 to 6 carbon atoms or for aryl or arylalkyl with 1 to 4 carbon atoms in the alkyl part which is optionally substituted in the aryl part by halogen, cyano, nitro, alkyl or alkoxy with 1 to 4 carbon atoms,
R⁶ stands for alkyl with 1 to 6 carbon atoms or for aryl or arylalkyl with 1 to 4 carbon atoms in the alkyl part which is optionally substituted in the aryl part by halogen, cyano, nitro, alkyl or alkoxy with 1 to 4 carbon atoms,
R⁷ represents hydrogen, alkyl having 1 to 6 carbon atoms or aryl or arylalkyl having 1 to 4 carbon atoms in the alkyl part, which is optionally substituted in the aryl part by halogen, cyano, nitro, alkyl or alkoxy each having 1 to 4 carbon atoms,
R⁸ stands for alkyl with 1 to 6 carbon atoms or for aryl or arylalkyl with 1 to 4 carbon atoms in the alkyl part which is optionally substituted in the aryl part by halogen, cyano, nitro, alkyl or alkoxy with 1 to 4 carbon atoms, or
R⁷ and R⁸ together with the nitrogen atom to which they are attached represent an optionally substituted by methyl, heterocyclic ring,
R⁹ for alkyl with 1 to 6 carbon atoms, dialkylamino each with 1 to 4 carbon atoms in the individual alkyl parts, nitrogen-bonded heterocyclyl with 3 to 7 ring members or for each optionally in the aryl part by halogen, cyano, nitro, alkyl or alkoxy each with 1 up to 4 carbon atoms is substituted aryl or arylalkyl with 1 to 4 carbon atoms in the alkyl part,
R³ represents hydrogen or alkyl having 1 to 4 carbon atoms,
R⁴ represents aryl, cycloalkyl or cycloalkenyl with 3 to 8 carbon atoms, which may be mono- or polysubstituted in the same or different ways, or heterocyclyl with 3 to 12 ring members, the possible substituents preferably being selected from the list below:
Halogen, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl;
in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms;
each straight-chain or branched alkenyl or alkenyloxy each having 2 to 6 carbon atoms;
each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkyl sulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
each straight-chain or branched haloalkenyl or haloalkenyloxy each having 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
each straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydroximinoalkyl or alkoximinoalkyl each having 1 to 6 carbon atoms in the individual alkyl parts;
each optionally singly or multiply, identically or differently by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, in each case doubly linked alkylene or dioxyalkylene each having 1 to 6 carbon atoms;
Cycloalkyl of 3 to 6 carbon atoms;
and in each case, if appropriate, once or several times, identically or differently
Halogen, cyano and / or straight-chain or branched alkyl having 1 to 4 carbon atoms
and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms
and / or straight-chain or branched alkoxy or alkylthio with 1 to 4 carbon atoms
and / or straight-chain or branched haloalkoxy or haloalkylthio having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms
and / or optionally mono- or polysubstituted, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms , each double-linked alkylene or dioxyalkylene each having 1 to 6 carbon atoms,
substituted aryl, aryloxy, arylthio, arylalkyl, arylalkyloxy, arylalkylthio, heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylalkyl, heterocyclylalkyloxy or heterocyclylalkylthio. 3. Compounds of formula (I) according to claim 1, in which
A for a single bond or for in each case optionally single or multiple, identical or different methylene, 1,1-ethylene, 1,2-ethylene 1,1-, 1,2-, 1,3 substituted by fluorine, chlorine, cyano or methoxy - or 2,2-propylene, 1,1-, 1,2-, 1,3-, 1,4-, 2,2-, 2,3-butylene or 1,1-, 1,2- or 1 , 3- (2-methyl-propylene) stands,
Q represents oxygen or sulfur,
R¹ for a tricyclic stands in what
G¹ and G² independently represent a single bond, alkanediyl, alkenediyl, oxygen, sulfur, -NH-, -N (alkyl) - or carbonyl and
G³ and G⁴ independently for nitrogen or a group stand and
Y¹, Y², Y³, Y⁴, Y⁵, Y⁶, Y⁷ and Y⁸ independently of one another for 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, methylamino, ethylamino, n- or i-propylamino, cyclo, cyclo, cyclo, methyl, cyclo
R² for hydroxy, amino or in each case optionally substituted by halogen, cyano, methoxy or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, vinyl, allyl, propargyl, methoxy, ethoxy , Allyloxy, propargyloxy, methylamino, ethylamino, dimethylamino, each optionally substituted by halogen, cyano, methoxy or ethoxy-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentyloxy, cyclohexyloxy, cyclopentylamino, cyclohexylamino or in each case optionally substituted phenyl, benzyl, benzyl , Phenylamino or heterocyclyl with 3 to 8 ring members, the possible substituents preferably being selected from the list below:
Fluorine, chlorine, bromine, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluorethoxy, difluoromethylthioifluoromifluoromethylthioifluoromethylthioifluoromifluoromethylthio, trifluoromethylfluoromethyl, trifluoromethylfluoromifluoromethyl, trifluoromethylfluoromethyl, trifluoromethylfluoromethyl, trifluoromethyl or trifluoromethyl, , Methylamino, ethylamino, n- or i-propylamino, dimethylamino, diethylamino, acetyl, propionyl, acetyloxy, methoxycarbonyl, ethoxycarbonyl, methylsulfonyloxy, ethylsulfonyloxy, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, ethoximino methyl, methoximinoethyl or
each optionally singly or multiply, the same or different by fluorine, chlorine, methyl, trifluoromethyl, ethyl, n- or i-propyl substituted, each doubly linked trimethylene (propane-1,3-diyl), tetramethylene (1,4-butane -diyl), methylenedioxy or ethylenedioxy,
Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, or
R² represents one of the following groups: wherein
Q¹ and Q² independently of one another represent oxygen or sulfur,
R⁵ for hydrogen or methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or for each optionally in the phenyl part by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy or ethoxy-substituted phenyl, benzyl, 1-phenylethyl or 2-phenylethyl,
R⁶ for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or for each optionally in the phenyl part by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i Propyl, n-, i-, s- or t-butyl, methoxy or ethoxy substituted phenyl, benzyl, 1-phenylethyl or 2-phenylethyl,
R⁷ for hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or for each optionally in the phenyl part by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy or ethoxy-substituted phenyl, benzyl, 1-phenylethyl or 2-phenylethyl,
R⁸ for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or for each optionally in the phenyl part by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i - Propyl, n-, i-, s- or t-butyl, methoxy or ethoxy substituted phenyl, benzyl, 1-phenylethyl or 2-phenylethyl, or
R⁷ and R⁸ together with the nitrogen atom to which they are attached represent an optionally substituted by methyl, heterocyclic ring,
R⁹ for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, dimethylamino, diethylamino, pyrrolidin-1-yl, morpholin-N-yl, piperidin-1-yl or for each phenyl, benzyl, 1-phenylethyl or optionally substituted in the phenyl part by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy or ethoxy 2-phenylethyl,
R³ represents hydrogen or methyl or ethyl,
R⁴ for each optionally monosubstituted to trisubstituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, phenyl, naphthyl, furyl, benzofuranyl, pyrrolyl, indolyl, thienyl, benzothienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, pyridimolylyl, pyridylolyl, pyridimolyl, pyridimolyl, , Pyridazinyl, pyrazinyl, oxiranyl, oxetanyl, tetrahydrofuryl, perhydropyranyl, pyrrolidinyl, piperidinyl or morpholinyl, where the possible substituents are preferably selected from the list below:
Fluorine, chlorine, bromine, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluorethoxy, diformifluoromethylthioifluoromifluoromethylthio, trifluoromethylfluoromethyl, trifluoromethylfluoromethyl, trifluoromethylfluoromethyl, trifluoromethylfluoromethyl, trifluoromethylfluoromethyl, trifluoromethylfluoromethyl, trifluoromethylfluoromethyl, trifluoromethylfluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl and trifluoromethyl , Methylamino, ethylamino, n- or i-propylamino, dimethylamino, diethylamino, acetyl, propionyl, acetyloxy, methoxycarbonyl, ethoxycarbonyl, methylsulfonyloxy, ethyl sulfonyloxy, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl or ethoximinoethyl or ethoximinoethyl or
each optionally mono- or polysubstituted, identically or differently, by fluorine, chlorine, methyl, trifluoromethyl, ethyl, n- or i-propyl, in each case doubly linked trimethylene (propane-1,3-diyl), tetramethylene (butane-1,4- diyl), methylenedioxy or ethylenedioxy,
Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. 4. Compounds of formula (I) according to claim 1, in which
A for a single bond or for optionally single or multiple, identical or different, methylene, 1,1-ethylene, 1,2-ethylene 1,1-, 1,2-, 1,3- substituted by fluorine, chlorine, cyano, methoxy or 2,2-propylene, 1,1-, 1,2-, 1,3-, 1,4-, 2,2-, 2,3-butylene or 1,1-, 1,2- or 1, 3- (2-methyl-propylene) stands,
Q represents oxygen or sulfur,
R¹ for a tricyclic stands in what
Y¹, Y², Y³, Y⁴, Y⁵, Y⁶, Y⁷ and Y⁸ independently of one another for 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, methylamino, ethylamino, n- or i-propylamyl, cyclo, methyl, cyclo, methyl, cyclo, methyl, cyclo, methyl, cyclo, methyl, cyclo,
R² for hydroxy, amino, methyl, fluoromethyl, difluoromethyl, trifluoromethyl, cyanophenyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, vinyl, allyl, methoxy, fluoromethoxy, difluoromethoxy, difluorochloromethoxy, Trifluoromethoxy, cyanomethoxy, ethoxy, allyloxy, methylamino, ethylamino, dimethylamino, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentyloxy, cyclohexyloxy, cyclopentylamino, cyclohexylamino or optionally optionally substituted phenyl, benzylthino-1-yl, benzylrolidyl, benzylryl, benzylryl, pyryll , Morpholin-N-yl, piperidin-1-yl, benzofuranyl, thienyl, benzothienyl, pyridyl, quinolyl, tetra hydrofuryl or perhydropyranyl, the possible substituents preferably being selected from the list below:
Fluorine, chlorine, bromine, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluorethoxy, diformifluoromethylthioifluoromifluoromethylthio, trifluoromethylfluoromethyl, trifluoromethylfluoromethyl, trifluoromethylfluoromethyl, trifluoromethylfluoromethyl, trifluoromethylfluoromethyl, trifluoromethylfluoromethyl, trifluoromethylfluoromethyl, trifluoromethylfluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl and trifluoromethyl , Methylamino, Ethylamino, n- or i-Propylamino, Dimethylamino, Diethylamino, Acetyl, Propionyl, Acetyloxy, Meth oxycarbonyl, Ethoxycarbonyl, Methylsulfonyloxy, Ethylsulfonyloxy, Hydroximinomethyl, Hydroximinoethyl, Methoximinomethyl, Ethoximinomethyl, in each case the same or methoximinoethyl, in the same way simple or methoximinoethyl, same as same or methoximinoethyl, same or more simply, or methoximinoethyl, same as same or more easily or differently, in each case doubly linked trimeth, substituted by fluorine, chlorine, methyl, trifluoromethyl, ethyl, n- or i-propyl ylene (propane-1,3-diyl), tetramethylene (butane-1,4-diyl), methylenedioxy or ethylenedioxy,
Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, or
R² represents one of the following groups: wherein
Q¹ and Q² independently of one another represent oxygen or sulfur,
R⁵ for hydrogen or methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or for each optionally in the phenyl part by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n - or i-propyl, n-, i-, s- or t-butyl, methoxy or ethoxy substituted phenyl, benzyl, 1-phenylethyl or 2-phenylethyl,
R⁶ for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or for each optionally in the phenyl part by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i Propyl, n-, i-, s- or t-butyl, methoxy or ethoxy substituted phenyl, benzyl, 1-phenylethyl or 2-phenylethyl,
R⁷ for hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or for each optionally in the phenyl part by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy or ethoxy-substituted phenyl, benzyl, 1-phenylethyl or 2-phenylethyl,
R⁸ for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or for each optionally in the phenyl part by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i - Propyl, n-, i-, s- or t-butyl, methoxy or ethoxy substituted phenyl, benzyl, 1-phenylethyl or 2-phenylethyl, or
R⁷ and R⁸ together with the nitrogen atom to which they are attached represent an optionally substituted by methyl, heterocyclic ring,
R⁹ for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, dimethylamino, diethylamino, pyrrolidin-1-yl, morpholin-N-yl, piperidin-1-yl or for each phenyl, benzyl, 1-phenyl or optionally substituted in the phenyl part by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy or ethoxy 2-phenylethyl,
R³ represents hydrogen or methyl,
R⁴ represents cyclo propyl, cyclobutyl, cyclopentyl or cyclohexyl which is optionally monosubstituted to six times, the preferred substituents being those mentioned below;
for in each case monosubstituted to trisubstituted phenyl, naphthyl, furyl, benzofuranyl, pyrrolyl, indolyl, thienyl, benzothienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridyl, quinolyl, pyrimidyl, pyridaziryl, pyridazinyl Tetrahydrofuryl, perhydropyranyl, pyrrolidinyl, piperidinyl or morpholinyl, where the possible substituents are preferably selected from the list below:
Fluorine, chlorine, bromine, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluorethoxy, diformifluoromethylthio, difluoromifluoromethio, diformifluoromethylthio, difluoromifluoromethyl, difluoromifluoromethyl, Methylamino, ethylamino, n- or i-propylamino, dimethylamino, diethylamino, acetyl, propionyl, acetyloxy, methoxycarbonyl, ethoxycarbonyl, methylsulfonyloxy, ethyl sulfonyloxy, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl, if necessary, multiple times Identically or differently, trimet substituted in each case by fluorine, chlorine, methyl, trifluoromethyl, ethyl, n- or i-propyl ethylene (propane-1,3-diyl), tetramethylene (butane-1,4-diyl), methylenedioxy or ethylenedioxy,
Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. 5. Compounds of formula (I) according to claim 1, in which
A represents a single bond or methylene, 1,1-ethylene, 1,2-ethylene, 1,1-propylene, 1,2-propylene, 1,3-propylene or 2,2-propylene,
Q represents oxygen,
R¹ for a tricyclic stands in what
Y¹, Y², Y³, Y⁴, Y⁵, Y⁶, Y⁷ and Y⁸ independently of one another for 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, methylamino, ethylamino, n- or i-propylamino, cyclo, cyclo, cyclo, methyl, cyclo
R² represents one of the following groups: wherein
Q¹ and Q² represent oxygen,
R⁵ for hydrogen or methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or for each optionally in the phenyl part by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n - or i-propyl, n-, i-, s- or t-butyl, methoxy or ethoxy substituted phenyl, benzyl, 1-phenylethyl or 2-phenylethyl,
R⁶ for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or for each optionally in the phenyl part by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i Propyl, n-, i-, s- or t-butyl, methoxy or ethoxy is substituted phenyl, benzyl, 1-phenylethyl or 2-phenylethyl,
R⁷ for hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or for each optionally in the phenyl part by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy or ethoxy-substituted phenyl, benzyl, 1-phenylethyl or 2-phenylethyl,
R⁸ for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or for each optionally in the phenyl part by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i - Propyl, n-, i-, s- or t-butyl, methoxy or ethoxy substituted phenyl, benzyl, 1-phenylethyl or 2-phenylethyl, or
R⁷ and R⁸ together with the nitrogen atom to which they are attached represent an optionally substituted by methyl, heterocyclic ring,
R⁹ for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, dimethylamino, diethylamino, pyrrolidin-1-yl, morpholin-N-yl, piperidin-1-yl or for each phenyl, benzyl, 1-phenylethyl or optionally substituted in the phenyl part by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy or ethoxy 2-phenylethyl,
R³ represents hydrogen or methyl,
R⁴ represents cyclohexyl or optionally mono- to triple-substituted phenyl, thienyl, furyl, benzofuryl, benzothienyl, pyridyl, pyrimidinyl, naphthyl, quinolyl, the possible sub-substituents preferably being selected from the list below:
Fluorine, chlorine, bromine, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluorethoxy, diformifluoromethylthioifluoromifluoromethylthio, trifluoromethylfluoromethyl, trifluoromethylfluoromethyl, trifluoromethylfluoromethyl, trifluoromethylfluoromethyl, trifluoromethylfluoromethyl, trifluoromethylfluoromethyl, trifluoromethylfluoromethyl, trifluoromethylfluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl and trifluoromethyl , Methylamino, ethylamino, n- or i-propylamino, dimethylamino, diethylamino, acetyl, propionyl, acetyloxy, methoxycarbonyl, ethoxycarbonyl, methylsulfonyloxy, ethyl sulfonyloxy, hydroximinomethyl, hydroximinoethyl, methoximino methyl, ethoximinomethyl, methoximinoethyl or ethoximinoethyl
each optionally mono- or polysubstituted, identically or differently, by fluorine, chlorine, methyl, trifluoromethyl, ethyl, n- or i-propyl, in each case doubly linked trimethylene (propane-1,3-diyl), tetramethylene (butane-1,4- diyl), methylenedioxy or ethylenedioxy. 6. pesticide, characterized by a content of at least one compound of formula (I) according to claim 1. 7. A method for controlling pests, characterized in that compounds of formula (I) according to claim 1 for pests and / or lets their living space take effect. 8. Uses of compounds of formula (I) according to claims 1 to 5 for pest control. 9. Process for the preparation of pesticides, thereby characterized in that compounds of formula (I) according to claims 1 to 5 mixed with extenders and / or surface-active agents.