DE19508573A1 - Imidic acid derivatives - Google Patents

Abstract

The invention pertains to new imidic acid derivatives of formula (I), methods for preparing them and their use as pesticides.

Description

The present invention relates to new imidic acid derivatives, several processes for their Manufacture and its use as a pesticide.

It is known that various substituted alkoximino and alkoxymethylene have acetamide fungicidal properties (see, for example, EP-A 398 692, EP-A 468 775, DE-A 40 30 038 and WO-A 92/13 830).

The effectiveness of these previously known compounds is, however, in particular low application rates and concentrations not in all areas of application completely satisfactory.

New imidic acid derivatives of the general formula (I) have been found

in which
R represents hydrogen, cyano or the groupings -CO-R¹, -CS-R² and -S (O) _m -R³,
in which
R¹, R² and R³ each represent alkyl, alkoxy, alkylthio, amino, alkylamino or dialkylamino and
m represents the numbers 0, 1 or 2;
X represents alkoxy, alkylthio, amino, alkylamino or dialkylamino, or
X and R together with the carbon or nitrogen atom to which they are bound, for a triazole radical of the formula

stand where
R⁶ represents alkyl, hydroxy, mercapto, amino, alkylamino or dialkyl amino;
Ar stands for optionally substituted arylene or heteroarylene;
G stands for a single bond for oxygen, for alkanediyl, alkenediyl, oxaalkenediyl, alkynediyl or one of the following groups, each optionally substituted by halogen, hydroxy, alkyl, haloalkyl or cycloalkyl:

-Q-CQ-, -CQ-Q-, -CH₂-Q-; -Q-CH₂-, -CQ-Q-CH₂-, -CH₂-Q-CQ-, -Q-CQ-CH₂-, -Q-CQ-Q-CH₂-, -N = N-, -S (O ) _n -, -CH₂-S (O) _n -, -CQ-, -S (O) _n -CH₂-, -C (R⁴) = NO-, -C (R⁴) = NO-CH₂-, -QC (R⁴) = NO-CH₂, -NH-C (R⁴) = NO-CH₂-, -N (R⁵) -, -CQ-N (R⁵) -, -N (R⁵) -CQ-, -Q-CQ -N (R⁵) -, -N = C (R⁴) -Q-CH₂-, -CH₂-ON = C (R⁴) -, -N (R⁵) -CQ-Q-, -CQ-N (R⁵) - CQ-Q-, -N (R⁵) -CQ-Q-CH₂-, -CQ-CH₂- or -N = NC (R⁴) = NO-,

in which
Q represents oxygen or sulfur,
n represents the numbers 0, 1 or 2,
R⁴ represents hydrogen, cyano or in each case optionally substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or cycloalkyl, and
R⁵ represents hydrogen, hydroxy, cyano or in each case optionally substituted alkyl, alkoxy or cycloalkyl; and
Z represents optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl or heterocyclyl;
with the exception of the compounds in which R simultaneously stands for hydrogen, G stands for oxygen or the group -OCH₂- and Z stands for optionally substituted aryl or 2-pyridyl.

It was also found that the new imidic acid derivatives of the general Formula (I) is obtained if

• a) nitriles of the general formula (II) in which
  Ar, G and Z have the meaning given above,
  with (thio) alcohols of the general formula (III) H-X¹ (III) in which
  X¹ represents alkoxy or alkylthio,
  or their alkali metal salts, if appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary;
  or
• b) the imido esters of the general formula (Ia) obtainable according to process (a) in which
  Ar, G, Z and X¹ have the meaning given above,
  with reactive acid derivatives, in particular with acid halides of the general formula (IV) HaI-R (IV) in which
  R has the meaning given above and
  Hal stands for halogen,
  or the corresponding anhydrides, if appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary;
  or
• c) the imido esters of the general formula (Ia) obtainable according to process (a) in which
  Ar, G, Z and X¹ have the meaning given above,
  with cyanamide of the formula (V) NH₂-CN (V) optionally in the presence of a diluent and optionally in the presence of a reaction auxiliary;
  or
• d) the imidic acid derivatives of the general formula (Ib) obtainable according to processes (b) and (c) in which
  Ar, G, Z and X¹ have the meaning given above and
  R ′ represents cyano or the groups -COR¹, -CSR² and -S (O) _m R³, where R¹, R², R³ and m have the meaning given above,
  with amines of the general formula (VI) H-X² (VI) in which
  X² represents amino, alkylamino or dialkylamino,
  if appropriate in the presence of a diluent;
  or
• e) the imidic acid derivatives of the general formula (Ic) obtainable according to processes (b) and (c) in which
  Ar, G, Z and R ′ have the meaning given above,
  with hydrazine or hydrazine hydrate, optionally in the presence of a diluent;
  or
• f) the imido esters of the general formula (Ia) obtainable according to process (a) in which
  Ar, G, Z and X¹ have the meaning given above,
  with amines of the general formula (VI) H-X² (VI) in which
  X² has the meaning given above,
  if appropriate in the presence of a diluent.

Finally, it was found that the new imidic acid derivatives of the general formula (I) show strong fungicidal activity.

The compounds according to the invention can optionally be mixed various possible isomeric forms, in particular E and Z isomers, exist Both the E and the Z isomers as well as any mixtures claimed these isomers.  

The invention preferably relates to compounds of the formula (I) in which
R represents hydrogen, cyano or the groupings -CO-R¹, -CS-R² and -S (O) _m -R³,
in which
R¹, R² and R³ each represent straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 4 carbon atoms;
Amino or straight-chain or branched alkyl amino and dialkylamino each with 1 to 4 carbon atoms in the individual alkyl parts and
m stands for the numbers 0, 1 or 2.
X represents in each case straight-chain or branched alkoxy or alkylthio each having 1 to 4 carbon atoms;
Amino or straight-chain or branched alkylamino and dialkylamino each having 1 to 4 carbon atoms in the individual alkyl parts.
X and R together with the carbon or nitrogen atom to which they are bound, for a triazole radical of the formula

stand where
R⁶ stands for straight-chain or branched alkyl having 1 to 4 carbon atoms, hydroxy, mercapto, amino or straight-chain or branched alkylamino and dialkylamino each having 1 to 4 carbon atoms in the individual alkyl parts.
Ar stands for optionally substituted phenylene or naphthylene or for heteroarylene with 5 or 6 ring members, at least one of which is oxygen, sulfur or nitrogen and optionally one or two more are nitrogen, the possible substituents preferably from the list below are selected:
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, in each case ge straight-chain or branched alkenyl, alkenyloxy or alkynyloxy 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 halogen alkenyl 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, alkoxy carbonyl, alkylsulfonyloxy, hydroximinoalkyl or alkoximinoalkyl, each with 1 to 6 carbon atoms in the individual alkyl parts, each optionally singly or multiply, 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 having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, in each case doubly linked alkylene or Dioxyalkylene, each with 1 to 6 carbon atoms.
G for a single bond, for oxygen, for in each case optionally substituted by halogen, hydroxy, C₁-C₄-alkyl, C₁-C₄-haloalkyl or C₃-C₆-cycloalkyl, alkanediyl, alkenediyl, oxaalkenediyl, alkynediyl with up to 4 carbon atoms or one of the the following groups are:

-Q-CQ-, -CQ-Q-, -CH₂-Q-; -Q-CH₂-, -CQ-Q-CH₂-, -CH₂-Q-CQ-, -Q-CQ-CH₂-, -Q-CQ-Q-CH₂-, -N = N-, -S (O ) _n -, -CH₂-S (O) _n -, -CQ-, -S (O) _n -CH₂-, -C (R⁴) = NO-, -C (R⁴) = NO-CH₂-, -QC (R⁴) = NO-CH₂-, -NH-C (R⁴) = NO-CH²-, -N (R⁵) -, -CQ-N (R⁵) -, -N (R⁵) -CQ-, -Q- CQ-N (R⁵) -, -N = C (R⁴) -Q-CH₂-, -CH₂-ON = C (R⁴) -, -N (R⁵) -CQ-Q-, -CQ-N (R⁵) -CQ-Q-, -N (R⁵) -CQ-Q-CH₂-, -CQ-CH₂- or -N = NC (R⁴) = N-,

in which
n represents the numbers 0, 1 or 2,
Q represents oxygen or sulfur,
R⁴ for hydrogen, cyano, for alkyl, alkoxy, alkylthio, alkylamino or dialkylamino optionally substituted by halogen, cyano or C₁-C₄alkoxy, each having 1 to 6 carbon atoms in the alkyl groups or for each optionally halogen, cyano, carboxy, C₁- C₄-alkyl or C₁-C₄-alkoxy-carbonyl substituted cycloalkyl having 3 to 6 carbon atoms, and
R⁵ represents hydrogen, hydroxyl, cyano or alkyl which has 1 to 6 carbon atoms and is optionally substituted by halogen, cyano or C₁-C₄alkoxy or represents optionally substituted by halogen, cyano, carboxy, C₁-C₄alkyl or C₁-C₄alkoxy- carbonyl substituted cycloalkyl having 3 to 6 carbon atoms.
Z for alkyl optionally substituted by halogen, cyano, hydroxy, amino, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl or C₁-C₄-alkylsulfonyl (which are each optionally substituted by halogen) with 1 to 8 Carbon atoms, each for alkenyl or alkynyl optionally substituted by halogen, each having up to 8 carbon atoms, each optionally for halogen, cyano, carboxy, phenyl (which may optionally be halogen, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy is substituted), C₁-C₄-alkyl or C₁-C₄-alkoxy-carbonyl-substituted cycloalkyl having 3 to 6 carbon atoms, for each optionally substituted phenyl, naphthyl or (optionally benzylated) heterocyclyl 5 or 6 ring members, at least one of which is oxygen, sulfur or nitrogen and optionally one or two more are nitrogen, where the possible substituents are preferably selected from the list below:
Oxygen (as a substitute for two geminal hydrogen atoms), halogen, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl, each straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl, each with 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, halogen alkylthio, 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 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, each straight-chain or branched alkylamino, dialkyl amino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydroximinoalkyl or alkoximinoalkyl, each having 1 to 6 carbon atoms in the one 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 dioxyalkylene each having 1 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, heterocyclyl or heterocyclyl-methyl each having 3 to 7 ring members, of which 1 to 3 are identical or different heteroatoms - in particular nitrogen, oxygen and / or sulfur -, and in each case optionally in the phenyl moiety one or more times, identically or differently, by halogen, cyano, nitro, carboxy, carbamoyl 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 same or different hied halogen atoms and / or straight-chain or branched alkoxy having 1 to 4 carbon atoms and / or straight-chain or branched haloalkoxy having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms and / or alkylcarbonyl or alkoxy carbonyl each having up to 5 carbon atoms substituted phenyl , Phenoxy, benzyl, benzyloxy, phenylethyl or phenylethyloxy;
the connections excluded by disclaimer above are excluded.

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.

The invention relates in particular to compounds of the formula (I) in which
R represents hydrogen, cyano or the groupings -CO-R¹, -CS-R² and -S (O) _m -R³,
in which
R¹ is methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl; Methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy; Methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio; Amino, methylamino, ethylamino, n- or i-propylamino; Dimethylamino, methyl-ethyl-amino, diethylamino, methyl-n- or i-propylamino and ethyl-n- or i-propylamino;
R² is methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl; Methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy; Methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio; Amino, methylamino, ethylamino, n- or i-propylamino; Dimethylamino, methyl-ethyl-amino, diethylamino, methyl-n- or i-propylamino and ethyl-n- or i-propylamino;
R³ is methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl; Methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy; Methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio; Amino, methylamino, ethylamino, n- or i-propylamino; Dimethylamino, methyl-ethyl-amino, diethylamino, methyl-n- or i-propylamino and ethyl-n- or i-propylamino; and
m stands for the numbers 0, 1 or 2.
X is methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy; Methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio; Amino, methylamino, ethylamino, n- or i-propylamino; Dimethylamino, methyl-ethyl-amino, diethylamino, methyl-n- or i-propylamino and ethyl-n- or i-propylamino.
X and R together with the carbon or nitrogen atom to which they are bound, for a triazole radical of the formula

stand where
R⁶ is methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl; Hydroxy; Mercapto; Amino, methylamino, ethylamino, n- or i-propyl amino; Dimethylamino, methyl-ethyl-amino, diethylamino, methyl-n- or i-propylamino and ethyl-n- or i-propylamino.
Ar for each optionally substituted ortho-, meta- or para-phenylene, for furandiyl, thiophene diyl, pyrroldiyl, pyrazole diyl, triazole diyl, oxazole diyl, isoxazole diyl, thiazole diyl, isothiazole diyl, oxadiazole diyl, thiadiazole diyl, pyridinedinediyl, pyrimidinediyl, pyrimidinediyl, pyrimidinediyl , 4-triazinediyl or 1,2,3-triazinediyl, the possible substituents being selected in particular from the list below:
Fluorine, chlorine, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, methyl thio, methylsulfinyl or methylsulfonyl.
G for a single bond, for oxygen for methylene, dimethylene (ethane-1,2-diyl) optionally substituted by fluorine, chlorine, hydroxyl, methyl, ethyl, n- or i-propyl, trifluoromethyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl , Ethen-1,2-diyl, Ethin-1,2-diyl or one of the groupings below

-Q-CQ-, -CQ-Q-, -CH₂-Q-, -Q-CH₂-, -CQ-Q-CH₂-, -CH₂-Q-CQ-, -Q-CQ-CH₂-, -Q -CQ-Q-CH₂-, -N = N-, -S (O) _n -, -CH₂-S (O) _n -, -CQ-, -S (O) _n -CH₂-, -C (R⁴ ) = NO-, -C (R⁴) = NO-CH₂-, -QC (R⁴) = NO-CH₂-, -NH-C (R⁴) = NO-CH²-, -N (R⁵) -, -CQ- N (R⁵) -, -N (R⁵) -CQ-, -Q-CQ-N (R⁵) -, -N = C (R⁴) -Q-CH₂-, -CH₂-ON = C (R⁴) -, -N (R⁵) -CQ-Q-, -CQ-N (R⁵) -CQ-Q- or -N (R⁵) -CQ-Q-CH₂-,

in which
n represents the numbers 0, 1 or 2,
Q represents oxygen or sulfur,
R⁴ represents hydrogen, cyano, methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, methoxy, ethoxy, propoxy, butoxy, methylthio, optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy, Ethylthio, propylthio, butylthio, methylamino, ethylamino, propylamino, dimethylamino or diethylamino or for cyclopropyl, cyclobutyl, optionally substituted by fluorine, chlorine, cyano, carboxy, methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl, Cyclopentyl or cyclohexyl, and
R⁵ for hydrogen, hydroxyl, cyano or for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy , Chlorine, cyano, carboxy, methyl, ethyl, n- or i-propyl, methoxy carbonyl or ethoxycarbonyl substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
Z for methyl, ethyl optionally substituted by fluorine, chlorine, bromine, cyano, hydroxyl, amino, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl (which are each optionally substituted by fluorine and / or chlorine), n- or i-Propyl, n-, i-, s- or t-butyl, for allyl, crotonyl, 1-methyl-allyl, propargyl or 1-methyl-propargyl optionally substituted by fluorine, chlorine or bromine, for each optionally by fluorine, chlorine, bromine, cyano, carboxy, phenyl (which may be by fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, Trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy is substituted), methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, given for each if substituted phenyl, naphthyl, furyl, tetrahydrofuryl, benzofuryl, Tetra hydropyranyl, thienyl, benzothienyl, pyrrolyl, dihydropyrrolyl, tetrahydro pyrrolyl, benzopyrrolyl, benzodihydropyrrolyl, oxazolyl, benzoxazolyl, isoxazolyl, thiazolyl, benzothiazolyl, isothiazolyl, imidazolyl, oximidiazolyl, oximidiazolyl, benzimidiazolyl, benzimidiazolyl, benzimidiazolyl, 3-triazinyl, 1,2,4-triazinyl or 1,3,5-triazinyl, where the possible substituents are preferably selected from the list below:
Oxygen (as a substitute for two geminal hydrogen atoms), fluorine, chlorine, bromine, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarb amoyl, 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, difluoromethoxy, trifluoromethoxy, difluoromethylthio, trifluoromifluoromethyl or trifluoromethylsulfonyl, methylamino, ethylamino, n- or i-propylamino, dimethylamino, diethylamino, acetyl, propionyl, acetyloxy, methoxycarbonyl, ethoxycarbonyl, methylsulfonyloxy, ethylsulfonyloxy, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, optionally methoximinoethyl, ethoximinoethyl, simple methyloxymino , the same or different fluorine, chlorine, methyl, ethyl, n- or i-propyl substituted trimethylene (propane-1,3-diyl), methylenedioxy or ethylenedioxy, cyclo propyl, cyclobutyl, cyclopentyl or cyclohexyl, and in each case optionally in the phenyl moiety one or more times, identically or differently by fluorine, chlorine, bromine, cyano, nitro, carboxy, carbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, acetyl, methoxycarbonyl or ethoxycarbonyl substituted phenyl, phenoxy, benzyl or benzyloxy;
the connections excluded by disclaimer above are excluded.

A particularly preferred group of compounds according to the invention are those compounds of the formula (I) in which
R represents hydrogen, cyano or the groupings -CO-R¹, -CS-R² and -S (O) _m -R³, where
R1 is methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, amino, methylamino, ethylamino, dimethylamino or diethylamino;
R² represents methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, amino, methylamino, ethylamino, dimethylamino or diethylamino;
R³ represents methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, amino, methylamino, ethylamino, dimethylamino or diethylamino; and
m stands for the numbers 0, 1 or 2.
X represents methoxy, ethoxy, methylthio, ethylthio, amino, methylamino, ethylamino, dimethylamino or diethylamino.
X and R together with the carbon or nitrogen atom to which they are bound, for a triazole radical of the formula

stand where
R⁶ represents methyl, ethyl, hydroxy, mercapto or amino.
Ar represents ortho-phenylene, pyridine-2,3-diyl or thiophene-2,3-diyl.
G represents oxygen, methylene or one of the groupings below

-CH₂-O-, -O-CH₂-, -S (O) _n -, CH₂-S (O) _n -, -S (O) _n -CH₂-, -C (R⁴) = NO-, -ON = C (R⁴) -, -C (R⁴) = NO-CH₂-, -OC (R⁴) = NO-CH₂-, -NH-C (R⁴) = NO-CH₂-, -N (R⁵) - or - CH₂-ON = C (R⁴) - stands,

in which
n represents the numbers 0, 1 or 2,
R⁴ represents hydrogen, methyl or ethyl and
R⁵ represents hydrogen, methyl or ethyl.
Z represents optionally substituted phenyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl or 1,3,5-triazinyl, the possible substituents preferably being selected from the list below are:
Fluorine, chlorine, bromine, cyano, 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, difluoromethoxy, trifluoromethoxy, difluoromethylthio, trifluoro-methylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, ethoximinomethyl, Methox iminoethyl, ethoximinoethyl, in each case optionally monosubstituted or polysubstituted by identical or different Methylenedioxy or ethylenedioxy substituted by fluorine, chlorine, methyl or ethyl, and in each case optionally in the phenyl part singly or repeatedly, identically or differently by fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i- , s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy substituted phenyl, phenoxy, benzyl or benzyloxy;
the connections excluded by disclaimer above are excluded.

A very particularly preferred group of compounds according to the invention are those compounds of the formula (I) in which
Ar stands for ortho-phenylene and
R, X, G and Z have the general, preferred and particularly preferred meanings given above.

The general or preferred range definitions given above apply both to the end products of the formula (I) and accordingly 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.  

Examples of the compounds according to the invention are in Tables 1 to 42 listed:

Table 1

Table 2

Table 3

Table 4

Table 5

Table 6

Table 7

Table 8

Table 9

Table 10

Table 11

Table 12

Table 13

Table 14

Table 15

Table 16

Table 17

Table 18

Table 19

Table 20

Table 21

Table 22

Table 23

Table 24

Table 25

Table 26

Table 27

Table 28

Table 29

Table 30

Table 31

Table 32

Table 33

Table 34

Table 35

Table 36

Table 37

Table 38

Table 39

Table 40

Table 41

Table 42

Those used to carry out process (a) according to the invention as starting materials Nitriles required are generally defined by the formula (II). In formula (II) Ar, G and Z preferably or particularly preferably have those meanings, which have already been described above in connection with the description of the connections of the Formula (I) mentioned as preferred or particularly preferred for these substituents were.

The nitriles of the formula (II) are not yet known; however, in general known manner can be obtained by using amides of the general formula (VII)

in which
Ar, G and Z have the meaning given above,
with water-releasing agents, such as anhydrides, if appropriate in the presence of a reaction auxiliary, such as pyridine, at temperatures between 0 and 100 ° C, preferably between 0 and 50 ° C (see also the preparation examples).

The amides of the formula (VII) are known (cf., for example, EP-A 0 398 692) or can obtained in a generally known manner by the processes described therein be by z. B. corresponding ester derivatives (see, for example, EP A 0 253 213, EP-A 0 506 149, EP-A 0 463 488 or EP-A 0 398 692) with Reacts ammonia (see also the manufacturing examples).  

Ester derivatives of the general formula (IX)

in which
R⁴ and Z have the meaning given above,
Ar¹ represents optionally substituted ortho-phenylene, the substituents already mentioned for Ar being suitable and
Alk is alkyl, preferably C₁-C₄ alkyl, such as in particular methyl,
can also be obtained if ester derivatives of the general formula (X) (see, for example, EP-A 0 506 149 and EP-A 0 600 835)

in which
Ar¹, Alk, R⁴ and Z have the meaning given above,
in a known manner with a nitrosating agent, such as, for example, tert-butyl nitrile in a suitable solvent, such as, for example, tert-butanol, and in the presence of a suitable base, such as, for example, potassium tert-butoxide, first to give the corresponding oxime derivatives of the general Formula (Xa)

in which
Ar¹, Alk, R⁴ and Z have the meaning given above and
M represents hydrogen or a metal equivalent, such as, in particular, potassium or sodium,
implements; and then this
either converted directly into the ester derivatives of the formula (IX) by alkylation in the customary manner,
or after release and isolation of the oximes of the formula (Xa) with M = hydrogen using a base, such as, for example, potassium carbonate and an alkylating agent, such as, for example, dimethyl sulfate, in the presence of a suitable solvent, such as, for example, acetonitrile, in the ester derivatives of the formula (IX) converted (see also the manufacturing examples).

The ester derivatives of the general formula (X) can be obtained by first (1st stage) an oxime of the general formula (XI)

in which
R⁴ and Z have the meaning given above,
optionally in the presence of a diluent such as methanol, ethanol, dimethylformamide or N-methylpyrrolidone at temperatures between -20 ° C and 200 ° C using a base such as alkali metal alcoholates or metal hydrides, especially sodium hydride and potassium tert-butoxide in the corresponding Salt transferred and at the same temperature using a dichloro derivative of the general formula (XII)

in which
Ar¹ has the meaning given above,
to an O-iminooxymethyl derivative of the general formula (XIII)

in which
Ar¹, R⁴ and Z have the meaning given above,
is implemented, the dichloro derivative of the formula (XII) being equivalent, but also in any excess, preferably from 1 to 10 equivalents;
then (2nd stage) the O-iminoxymethyl derivatives of the formula (XIII) thus obtained with 1 to 5, preferably 1 to 1.1 equivalents of alkali metal cyanide in the presence of a diluent, such as, for example, acetone, acetonitrile, methyl ethyl ketone, dimethyl sulfoxide, toluene, Methanol, ethanol, isopropanol, butanol, tetrahydrofuran, dioxane or water at temperatures between 0 ° C and 100 ° C, preferably between 20 ° C and 50 ° C, optionally in the presence of a phase transfer catalyst such as tetra-n-butylammonium chloride, tetra n -butylammonium bromide, tetra-n-butylammonium hydrogen sulfate, tetramethylammonium bromide or benzyltriethylammonium chloride to form an acetic acid nitrile derivative of the general formula (XIV)

in which
Ar¹, R⁴ and Z have the meaning given above,
implements;
and then (3rd stage) the acetic acid nitrile derivatives of the formula (XIV) thus obtained in a generally customary and known manner
either directly by means of alcohol in the presence of an aqueous acid to give the ester derivatives of the formula (X);
or first by hydrolysis in the presence of strong bases or mineral acids into the corresponding acetic acid derivatives of the general formula (XV)

in which
Ar¹, R⁴ and Z have the meaning given above,
transferred and then converted to the ester derivatives of the formula (X) in a generally customary and known manner by means of alcohol in the presence of an acid or a base;
or first by means of an acid halide, such as in particular PCl₃, PCl₅, POCl₃, SOCl₂ or SO₂Cl₂ in the corresponding acetic acid halide derivatives of the general formula (XVI)

in which
Ar¹, R⁴ and Z have the meaning given above and
Hal represents halogen, preferably chlorine or bromine, in particular chlorine,
transferred and then converted to the ester derivatives of the formula (X) in a generally customary and known manner by means of alcohol, if appropriate in the presence of an acid binder (cf. also the preparation examples).

The oximes of formula (XI) and the dichloro derivatives of formula (XII) are general known compounds of organic chemistry or in a generally customary manner and Way to make.

The O-iminooxymethyl derivatives of the formula (XIII), the acetic acid nitrile derivatives of the Formula (XIV), the acetic acid derivatives of the formula (XV) and the Acetic acid halide derivatives of the formula (XVI) are new and also an object of this invention.

Nitriles of the formula (IIa)

in which
Ar¹, R⁴ and Z have the meaning given above,
can also be obtained by using 2-methoximino-2- (2-bromomethylphenyl) acetonitrile of the formula (XVII)

with oxime derivatives of the general formula (XVIII)

in which
R⁴ and Z have the meaning given above,
optionally in the form of their alkali metal salts in the presence of a diluent such as dimethylformamide and optionally in the presence of a base such as sodium or potassium hydride at temperatures between 0 and 100 ° C, preferably between 0 and 80 ° C (see also the preparation examples).

The 2-methoximino-2- (2-bromomethylphenyl) acetonitrile of the formula (XVII) is obtained by in a commonly used and known manner initially 2-methoximino-2- (2-methylphenyl) acetic acid methyl ester of the formula (XIX)

with ammonia in the 2-methoximino-2- (2-methylphenyl) acetamide of the formula (XX)

transferred;
this with dehydrating agents, such as anhydrides, optionally in the presence of a reaction auxiliary, such as pyridine, at temperatures between 0 and 100 ° C, preferably between 0 and 50 ° C for 2-methoximino-2- (2-methylphenyl) acetonitrile of the formula (XXI)

implements; and finally brominated the nitrile derivative of the formula (XXI) thus obtained, for example by reaction with N-bromosuccinimide in the presence of a Catalyst, such as dibenzoyl peroxide (see also the manufacturing games).

The compounds of the formulas (XVII), (XX) and (XXI) are new and also Subject of this invention.

The oxime derivatives of the general formula (XVIII) are known (cf., for example, Houben- Weyl "Methods of Organic Chemistry" Volume VII / I, pp. 413-488) or are in generally known way available.

The 2-methoximino-2- (2-methylphenyl) acetic acid methyl ester of the formula (XIX) is also known (see, for example, EP-A 0 400 417).  

Which also for performing the method (a) according to the invention as Formula (III) provides general means for (thio) alcohols required as starting materials Are defined. In the formula (III), X¹ preferably or particularly preferred those meanings already related to the description of the above Compounds of formula (I) as preferred or particularly preferred for X in its Meaning as alkoxy or alkylthio were mentioned.

The (thio) alcohols of the formula (III) and their alkali metal salts, such as for example sodium and potassium salts are well known compounds of the organic chemistry.

The to carry out the processes (b), (c) and (f) as Imidoesters required as starting materials are generally defined by the formula (Ia). In formula (Ia), Ar, G, Z and X¹ (for X in its meaning as alkoxy or Alkylthio) preferably or particularly preferably those meanings which already above in connection with the description of the compounds of the formula (I) have been mentioned as preferred or particularly preferred for these substituents.

The imido esters of the formula (Ia) are compounds according to the invention and according to Method (a) available.

Imidoesters of formula (Ia) in which X¹ is alkylthio can also be obtained by using amides of the general formula (VII) with a Sulfurizing agents such as B. P₄S₁₀ or Lawesson reagent, optionally in a diluent, such as. As xylene or toluene, at temperatures between 50 ° C and 200 ° C and the resulting thioamides of the general formula (VIII)

in which
Ar, G and Z have the meaning given above,
alkylated in the usual way.

Which also for performing the method (b) according to the invention as Formula (IV) generalizes acid halides required as starting materials Are defined. In formula (IV), R preferably or particularly preferably has those Meanings already related to the description of the Compounds of formula (I) as preferred or particularly preferred for this Substituents were called. Hal preferably represents fluorine, chlorine or bromine, particularly preferred for chlorine.

The acid halides of the formula (IV) are generally known compounds of organic chemistry.

That also to carry out the method (c) according to the invention as off Cyanamide of the formula (V) required as a starting material is also a generally known one Compound of organic chemistry.

Those used to carry out process (d) according to the invention as starting materials required imidic acid derivatives are generally defined by the formula (Ib). In the Formula (Ib) have Ar, G, Z, X¹ (for X in its meaning as alkoxy or Alkylthio) and R ′ (for R in its abovementioned meaning with the exception of Hydrogen) preferably or particularly preferably those meanings which already above in connection with the description of the compounds of the formula (I) have been mentioned as preferred or particularly preferred for these substituents.

The imidic acid derivatives of the formula (Ib) are compounds according to the invention and obtainable according to processes (b) and (c).  

Which also to carry out the processes (d) and (f) as The amines required as starting materials are generally defined by the formula (VI). In of formula (VI), X² preferably or particularly preferably has those Meanings already related to the description of the Compounds of formula (I) as preferred or particularly preferred for X in its Meaning as amino, alkylamino and dialkylamino were mentioned.

The amines of the formula (VI) are generally known compounds of the organic Chemistry.

Those used to carry out process (e) according to the invention as starting materials The imidic acid derivatives required are generally defined by the formula (Ic). In the Formula (Ic) have Ar, G, Z and R ′ (for R in its abovementioned meaning with Exception of hydrogen) preferably or particularly preferably those Meanings already related to the description of the Compounds of formula (I) as preferred or particularly preferred for these Substituents were called.

The imidic acid derivatives of the formula (Ic) are compounds according to the invention and obtainable according to processes (b) and (c).

That also to carry out the method (e) according to the invention as Hydrazine or hydrazine hydrate required as starting material is a generally known one Compound of organic chemistry.  

Suitable diluents for carrying out the process according to the invention Process (a) all inert organic reactions customary for such reactions Solvent in question. Ethers, such as diethyl ether, are preferably usable. Methyl tert-butyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or -diethyl ether; also nitriles, such as acetonitrile; and also if necessary halogenated aliphatic, cycloaliphatic and aromatic hydrocarbons, such as Methylene chloride, chloroform, carbon tetrachloride, hexane, cyclohexane, benzene, Toluene, xylene, chlorobenzene and petroleum ether.

Process (a) according to the invention is preferably carried out in the presence of a suitable reaction auxiliary. As such, everyone usually comes usable inorganic and organic bases in question. Preferably alkali metal hydrides, hydroxides, alcoholates, acetates, carbonates are used or hydrogen carbonates, such as sodium hydroxide, sodium methylate, Sodium ethylate, potassium t-butoxide, sodium acetate, potassium acetate, sodium carbonate, Potassium carbonate or sodium hydrogen carbonate or tertiary amines, such as for example triethylamine, N, N-dimethylaniline, pyridine, N, N-dimethylaminopyridine, Diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicycloundecene (DBU). Acidic reaction aids such as p-toluenesulfonic acid are also possibly an advantage.

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 works one at temperatures between 0 ° C and 200 ° C, preferably at temperatures between 0 ° C and 100 ° C.

To carry out process (a) according to the invention, nitrile is employed per mole of formula (II) generally 1 to 10 moles, preferably 1 to 5 moles of (thio) alcohol of the formula (III) or their alkali metal salts and optionally 1 to 10 Mol, preferably 1 to 5 moles of reaction aids. However, it is also a larger excess possible.  

As a diluent for carrying out process (b) according to the invention inert organic solvents are suitable. Are preferably usable aliphatic, alicyclic or aromatic, optionally halogenated carbons Hydrogen, such as gasoline, benzene, toluene, xylene, chlorobenzene, Petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ethers, such as diethyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or -diethyl ether or esters, such as ethyl acetate.

Process (b) according to the invention is preferably carried out in the presence of a suitable reaction auxiliary. As such, everyone usually comes usable inorganic and organic bases in question. Preferably alkali metal hydrides, hydroxides, alcoholates, acetates, carbonates are used or hydrogen carbonates, such as sodium hydroxide, sodium methylate, Sodium ethylate, potassium t-butoxide, sodium acetate, potassium acetate, sodium carbonate, Potassium carbonate or sodium bicarbonate or tertiary amines, as in for example triethylamine, N, N-dimethylaniline, pyridine, N, N-dimethylaminopyridine, Diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicycloundecene (DBU).

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 works one at temperatures between 0 ° C and 150 ° C, preferably at temperatures between 0 ° C and 100 ° C.

The process (b) according to the invention is carried out per mole Imido esters of formula (Ia) generally 0.8 to 5 mol, preferably 0.8 to 3 mol on acid derivative of the formula (IV) and optionally 1 to 5 mol, preferably 1 to 3 Mole of reaction auxiliary.  

As a diluent for carrying out process (c) according to the invention water and all water-miscible organic solvents are suitable including their mixtures with water. Alcohols such as B. methanol or ethanol.

Process (c) according to the invention is preferably used in the presence of a Neten reaction auxiliary carried out. As such, preferably come anorga African salts, such as alkali metal acetates, carbonates, hydrogen carbonates, phosphates, hydrogen phosphates or dihydrogen phosphates, such as sodium acetate, potassium acetate, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, Sodium phosphate, sodium dihydrogen phosphate and disodium hydrogen phosphate.

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 works one at temperatures between -20 ° C and + 100 ° C, preferably at temperatures between 0 ° C and 50 ° C.

The process (c) according to the invention is carried out per mole Imido esters of formula (Ia) generally 0.5 to 5 mol, preferably 0.5 to 2 mol of cyanamide of the formula (V) and optionally 2 to 20 mol, preferably 2 to 8 Mole of reaction auxiliary, the pH of the reaction mixture in generally between 4 and 9, preferably between 6 and 7.

As a diluent for carrying out processes (d) and (e) come water and all water-miscible inert organic solutions medium in question. Ethers such as dioxane and tetrahydrofuran can preferably be used or ethylene glycol dimethyl or diethyl ether, nitriles such as acetonitrile or propio nitrile, amides, such as dimethylformamide, dimethylacetamide, N-methylformanilide, N- Methyl pyrrolidone or hexamethyl phosphoric acid amide or sulfoxides such as dimethyl sulfoxide, alcohols such as methanol or ethanol or basic solvents such as Pyridine or triethylamine.  

The reaction temperatures can be carried out when carrying out the inventive Processes (d) and (e) can be varied over a wide range. In general one works at temperatures between -50 ° C and + 100 ° C, preferably at Temperatures between -20 ° C and + 50 ° C.

The process (d) according to the invention is preferably carried out in molar amounts; however, it is also possible to use the amine of the formula (VI) in larger amounts Use excess.

The process (e) according to the invention is carried out per mole Imidic acid derivative of the formula (Ic) generally 0.5 to 10 mol, preferably 0.5 to 5 mol of hydrazine or hydrazine hydrate.

As a diluent for carrying out process (f) according to the invention water and polar organic solvents are suitable. Preferably ethers such as diethyl ether, dioxane, tetrahydrofuran or Ethylene glycol dimethyl or diethyl ether and alcohols such as methanol or Ethanol. It is also possible to use the amine to be used as the reactant Use formula (VI).  

The reaction temperatures can be carried out when carrying out the process according to the invention Process (f) can be varied over a wide range. Generally works one at temperatures between -40 ° C and + 200 ° C, preferably at temperatures between 0 ° C and 100 ° C.

The process (f) according to the invention is preferably carried out in molar amounts; but it is also possible, in particular the amine of the formula (VI) use in larger excess.

When carrying out processes (a) to (f) according to the invention, the process is carried out in general under normal pressure. However, it is also possible to reduce or to work in particular and increased pressure.

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

The active compounds of the formula (I) according to the invention have a strong microbicidal action Effect on and can help fight unwanted microorganisms can be used practically. The active ingredients are for use as Plant protection products, particularly suitable as fungicides.

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

Some pathogens of fungal diseases that fall under the generic names listed above may be mentioned as examples, but not by way of limitation:
Pythium species, such as, for example, Pythium ultimum;
Phytophthora species, such as, for example, Phytophthora infestans;
Pseudoperonospora species, such as, for example, Pseudoperonospora humuli or Pseu doperonospora cubense;
Plasmopara species, such as, for example, Plasmopara viticola;
Peronospora species, such as, for example, Peronospora pisi or Peronospora 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 Pyrenophora graminea (conidial form: Drechslera, synonym: Helminthosporium);
Cochliobolus species, such as, for example, Cochliobolus sativus (conidial form: Drechs lera, synonym: Helminthosporium);
Uromyces species, such as, for example, Uromyces appendiculatus;
Puccinia species, such as, for example, Puccinia recondita;
Tilletia species, such as, for example, Tilletia caries;
Ustilago species, such as, for example, Ustilago nuda or Ustilago avenae;
Pellicularia species, such as, for example, Pellicularia sasakii;
Pyricularia species, such as, for example, Pyricularia oryzae;
Fusarium species, such as, for example, Fusarium culmorum;
Botrytis species, such as, for example, Botrytis cinerea;
Septoria species, such as, for example, Septoria nodorum;
Leptosphaeria species, such as, for example, Leptosphaeria nodorum;
Cercospora species, such as, for example, Cercospora canescens;
Alternaria species, such as, for example, Alternaria brassicae;
Pseudocercosporella species, such as, for example, Pseudocercosporella herpotrichoides.

The 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 soil.  

The active compounds according to the invention can be used with particularly good success Combating diseases in fruit and vegetable growing, such as against Podosphaera and Venturia species, for combating cereal diseases, such as for example against Erysiphe species, or for controlling rice diseases, such as for example against Pyricularia oryzae.

The active ingredients can depend on their respective physical and / or chemical properties are converted into conventional 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 the active ingredients with diluents, i.e. liquid solvents, are under pressure Liquefied gases and / or solid carriers, optionally under Use of surface-active agents, i.e. emulsifiers and / or dispersers yawing and / or foaming agents. In case of using water as an extender z. B. also organic solvents as auxiliary solvents be used. The following are essentially suitable as liquid solvents: Aro mat, such as xylene, toluene, alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes, or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. B. petroleum fractions, alcohols, such as butanol or glycol, and their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar Solvents, such as dimethylformamide or dimethyl sulfoxide, and water; With Liquefied 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, Nitrogen and carbon dioxide; as solid carriers come into question: B. natural Rock flours, such as kaolins, clays, talc, chalk, quartz, attapulgite, Mont morillonite or diatomaceous earth and synthetic rock powder, such as highly disperse Silica, alumina and silicates; come as solid carriers for granules in question: e.g. B. broken and fractionated natural rocks such as calcite, marble,  Pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours and granules made of organic material such as sawdust, Coconut shells, corn cobs and tobacco stalks; as emulsifying and / or foam Generating funds are possible: z. B. non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. B. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; as dispersants come into question: z. B. Ligninsulfitablaugen 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 phospho lipids 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.  

For the mixtures, for example:

Fungicides

2-aminobutane; 2-anilino-4-methyl-6-cyclopropyl-pyrimidine; 2 ′, 6′-dibromo-2-methyl-4′-trifluoromethoxy-4′-trifluoromethyl-1,3-thizole-5-carboxanilide; 2,6-dichloro-N- (4-trifluoromethylbenzyl) benzamide; (E) -2-methoxyimino-N-methyl-2- (2-phenoxyphenyl) acetamide; 8-hydroxyquinoline sulfate; Methyl- (E) -2- {2- [6- (2-cyano-phenoxy) pyrimidin-4-yloxy] phenyl} -3-methoxyacrylate; Methyl (E) methoximino [alpha- (o-tolyloxy) -o tolyl] acetate; 2-phenylphenol (OPP), aldimorph, ampropylfos, anilazine, azaconazole, benalaxyl, benodanil, benomyl, binapacryl, biphenyl, bitertanol, blasticidin-S, bromuconazole, bupirimate, buthiobate,
Calcium polysulfide, captafol, captan, carbendazim, carboxin, quinomethionate (quinomethionate), chloroneb, chloropicrin, chlorothalonil, chlozolinate, cufraneb, cymoxanil, cyproconazole, cyprofuram,
Dichlorophen, diclobutrazole, diclofluanid, diclomezin, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole, dinocap, diphenylamine, dipyrithione, ditalimfos, dithianon, dodine, drazoxolone,
Edifenphos, epoxyconazole, ethirimol, etridiazole,
Fenarimol, fenbuconazole, fenfuram, fenitropan, fenpiclonil, fenpropidin, fenpropi morph, fentinacetate, fentinhydroxyd, ferbam, ferimzone, fluazinam, fludioxonil, fluoromide, fluquinconazole, flusilazole, flusulfamide, flutolanil, futriafol, futriafol , Furmecyclox,
Guazatine,
Hexachlorobenzene, hexaconazole, hymexazole,
Imazalil, Imibenconazol, Iminoctadin, Iprobefos (IBP), Iprodione, Isoprothiolan,
Kasugamycin, copper preparations such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, oxine-copper and Bordeaux mixture,
Mancopper, Mancozeb, Maneb, Mepampyrim, Meproml, Metalaxyl, Metconazol, Methasulfocarb, Methfuroxam, Metiram, Metsulfovax, Myclobutaml,
Nickel dimethyldithiocarbamate, nitrothal isopropyl, nuanmol,
Ofurace, oxadixyl, oxamocarb, oxycarboxin,
Pefurazoate, penconazole, pencycuron, phosdiphen, pimaricin, piperalin, polyoxin, probenazole, prochloraz, procymidon, propamocarb, propiconazole, propineb, pyrazophos, pyrifenox, pyrimethanil, pyroquilon,
Quintozen (PCNB),
Sulfur and sulfur preparations,
Tebuconazole, tecloftalam, tecnazene, tetraconazole, thiabendazole, Thicyofen, thiophanate-methyl, thiram, Tolclophos-methyl, tolylfluanid, triadimefon, Triadi menol, triazoxide, Trichlamid, tricyclazole, tridemorph, triflumizole, triforine, triticonazole,
Validamycin A, vinclozolin,
Zineb, ziram

Bactericides

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

Insecticides / acaricides / nematicides

Abamectin, Abamectin, AC 303 630, Acephat, Acrinathrin, Alanycarb, Aldicarb, Alphamethrin, Amitraz, Avermectin, AZ 60541, Azadirachtin, Azinphos A, Azinphos M, Azocyclotin,
Bacillus thuringiensis, Bendiocarb, Benfüracarb, Bensultap, Betacyluthrin, Bifenthrin,
BPMC, Brofenprox, Bromophos A, Bufencarb, Buprofezin, Butocarboxin, Butylpyridaber,
Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, CGA 157 419, CGA 184699, Chloethocarb, Chlorethoxyfos, Chloretoxyfos, Chlorfenvinphos, Chlorfiuazuron, Chlormephos, Chlorpyrifos, Chlorpyrifos M, Cis-Resmethrinin, Clyanothrinhrin, Clyan Cyhalothrin, cyhexatin, cypermethrin, cyromazine,
Deltamethrin, Demeton M, Demeton S, Demeton-S-methyl, Diafenthiuron, Diazinon, Dichlofenthion, Dichlorvos, Dicliphos, Dicrotophos, Diethion, Diflubenzuron, Dimethoat, Dimethylvinphos, Dioxathion, Disulfoton,
Edifenphos, Emamectin, Esfenvalerat, Ethiofencarb, Ethion, Ethofenprox, Ethopro phos, Etofenprox, Etrimphos,
Fenamiphos, Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipronil, Fluazinam, Flucycloxuron, Flucythrinat, Flufenoxuron, Flufenproothate, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufone
HCH, heptenophos, hexaflumuron, hexythiazox,
Imidacloprid, Iprobefos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Ivemectin,
Lamda-cyhalothrin, Lufenuron,
Malathion, Mecarbam, Mervinphos, Mesulfenphos, Metaldehyde, Methacrifos, Methamidophos, Methidathion, Methiocarb, Methomyl, Metolcarb, Milbemectin, Monocrotophos, Moxidectin,
Naled, NC 184, NI 25, Nitenpyram
Omethoate, Oxamyl, Oxydemethon M, Oxydeprofos,
Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamdon, Phoxim, Pirimicarb, Pirimiphos M,, Primiphos A, Profenofos, Profenophos, Promecarb, Propaphos, Propoxur, Prothiofos, Prothiophos, Prothosincl, Pothophos, Pyrothicos , Pyraclophos, Pyradaphenthion, Pyresmethrin, Pyrethrum, Pyridaben, Pyrimidifen, Pyriproxifen,
Quinalphos,
RH 5992,
Salithion, Sebufos, Silafluofen, Sulfotep, Sulprofos,
Tebufenozid, tebufenpyrad, tebupirimphos, teflubenzuron, tefluthrin, Temephos, Terbam, Terbufos, Tetrachlorvinphos, Thiafenox, Thiodicarb, Thiofanox, Thio methon, Thionazin, Thuringiensin, Tralomethrononium, Triaromenontronium, Triaromenhroniaz, Triaratheniazin, Triaratheniazon
Vamidothione, XMC, xylylcarb, YI 5301/5302, zetamethrin.

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

The active substances can be used as such, in the form of their formulations or in the form thereof prepared application forms, such as ready-to-use solutions, suspensions, Spray powder, pastes, soluble powders, dusts and granules can be used. The application is done in the usual way, e.g. B. by pouring, spraying, Spraying, scattering, dusting, foaming, brushing, etc. It is further possible to apply the active ingredients using the ultra-low-volume process or to inject the active substance preparation or the active substance itself into the soil. It 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 generally mean 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 (Method a)

A solution of 11.3 g (0.03 mol) of E-2-methoximino-2- {2- [1- (3-trifluoromethylphenyl) ethylideniminoxymethyl] phenyl} acetonitrile and 13.0 g (0.24 mol) of sodium methanolate in 46 ml of methanol is stirred for 48 hours at room temperature. The solution is poured onto 3 l of water, extracted with ether, dried with potassium carbonate and concentrated. 12.2 g of a yellowish oil containing 80% (GC) of E-2-methoximino-2- {2- [1- (3-trifluoromethylphenyl) -ethylideniminoxy methyl] -phenyl} -acetimidic acid methyl ester are obtained.
1 H-NMR (CDC13): δ = 2.22; 3.86; 3.99; 5.11; 7.11-7.95.

Manufacture of the starting product (Version 1)

A solution of 2.8 g (0.007 mol) of E-2-methoximino-2- {2- [1- (3-trifluoromethylphenyl) ethylideniminoxymethyl] phenyl} acetamide in 5 ml pyridine is cooled to 0 ° C , 2.2 g (0.0105 mol) of triluoroacetic anhydride were added and the mixture was stirred at 0 ° C. for 2 hours and at room temperature for 18 hours. The solution is concentrated, the residue is taken up in ethyl acetate, washed with water and highly dilute hydrochloric acid, dried with magnesium sulfate and concentrated. The residue is chromatographed on silica gel using cyclohexane / ethyl acetate (3: 1). 1.8 g (69%) of E- 2-methoximino-2- (2- [1- (3-trifluoromethylphenyl) ethylideniminoxymethyl] phenyl} acetonitrile are obtained as a yellow oil (IR spectrum: 2200 cm ^-1 ).

In a solution of 32.6 g (0.08 mol) of E-2-methoximino-2- {2- [1- (3-trifluoromethyl phenyl) -ethylideniminoxymethyl] -phenyl} -acetic acid methyl ester in 200 ml of methanol is introduced at about 10 ° C until saturation of ammonia. It'll be another 2 hours stirred and then concentrated. The residue is stirred with hexane and aspirated. 23.8 g (76%) of E-2-methoximino-2- {2- [1- (3-trifluoromethyl phenyl) -ethylideniminoxymethyl] -phenyl} -acetamide with a melting point of 112 ° C.

To a suspension of 4.5 g (0.113 mol) sodium hydride in 80 ml dimethylformamide 19.1 g (0.094 mol) of 3-trifluoromethylacetophenone oxime are added and the mixture is stirred until End of gas evolution. Now 26.9 g (0.094 mol) of E-2-methoximino-2- (2- Bromomethylphenyl) -acetic acid methyl ester and stirred overnight at room temperature maturity. The solvent is distilled off and the residue is poured into 1 liter of water and extracted with ether. The organic phase is dried with magnesium sulfate and constricted. 34.2 g (89%) of E-2-methoximino-2- {2- [1- (3-trifluoromethyl phenyl) -ethylideniminoxymethyl] -phenyl} -acetic acid methyl ester as a brown oil.  

Alternative preparation of compound (IX-1) 1st stage

6.1 g (0.03 mol) of 3-trifluoromethylacetophenone oxime are dissolved in 30 ml of dimethyl formamide and converted into the salt by adding 1.2 g (0.03 mol) of 60% sodium hydride at room temperature by stirring for about 30 minutes . This salt solution is added dropwise to 21 g (0.12 mol) of α, α-dichloroxylene, which has been dissolved in 50 ml of dimethylformamide. The reaction mixture is heated at 50 ° C. for 1 hour and the mixture is distilled under high vacuum. After dimethylformamide and excess α, α-dichloroxylene have been distilled off, 8.4 g (81.9% of theory) of 2- [1- (3-trifluoromethylphenyl) ethylideniminoxy methyl] go at 0.3 Torr and 151 to 156 ° C. -benzyl chloride over.
1 H-NMR spectrum (CDCl₃ / TMS):
δ = 2.249 (3H); 4.751 (2H); 5.393 (2H); 7.299-7.39 (2H); 7.39-7.462 (3H); 7.563 / 7.589 (1H); 7.784 / 7.811 (1H); 7.895 (1H) p 18245 00070 552 001000280000000200012000285911813400040 0002019508573 00004 18126pm.

2nd stage

63.8 g (0.187 mol) of 2- [1- (3-trifluoromethylphenyl) ethylidene iminoxymethyl] benzyl chloride are added to 10.1 g (0.206 mol) of sodium cyanide in 200 ml of dimethyl sulfoxide and stirred for 12 hours at room temperature. The mixture is poured onto water, extracted with ethyl acetate, the organic phase is concentrated and the residue is stirred with low-boiling petroleum ether. 43 g (69.2% of theory) of 2- [1- (3-trifluoromethylphenyl) ethylideniminoxymethyl] phenylacetic acid nitrile are obtained.
1 H-NMR spectrum (CDCl₃ / TMS):
δ = 2.263 (3H); 3,899 (2H); 5.278 (2H); 7.249-7.506 (5H); 7.597 / 7.623 (1H); 7.788 / 7.814 (1H); 7.885 (1H) ppm.

3rd stage

15 g (0.045 mol) of 2- [1- (3-trifluoromethylphenyl) ethylideniminoxymethyl] phenyl acetic acid nitrile are stirred in 90 ml of ethylene glycol with 7 g (0.106 mol) of 85% KOH powder at 140 ° C. for 7 hours. It is poured onto water and extracted with ethyl acetate. Then acidified and the product extracted with dichloromethane. After stripping off the solvent, 13 g (82.2% of theory) of acid are obtained.
1 H-NMR spectrum (CDCl₃ / TMS):
δ = 2.181 (3H); 3.826 (2H); 5.291 (2H); 7.248-7.339 (3H); 7.421-7.468 (2H); 7.570 / 7.596 (1H); 7.761 / 7.787 (1H); 7.858 (1H) ppm.

4th stage

3.5 g (0.05 mol) of 2- [1- (3-trifluoromethylphenyl) ethylideniminoxymethyl] phenylacetic acid are refluxed in 10 ml of dichloroethane with 1.4 g (0.012 mol) of thionyl chloride for 2 hours. After the volatile constituents have been stripped off, 3.5 g (94.7% of theory) of crude 2- [1- (3-trifluoromethylphenyl) ethylideniminoxymethyl] phenylacetic acid chloride are obtained.
1 H-NMR spectrum (CDCl₃ / TMS):
δ = 2.236 (3H); 4,334 (2H); 5.268 (2H); 7.249-7.291 (1H); 7.357-7.387 (2H); 7.436 - 7.501 (2H); 7.593 / 7.619 (1H); 7.793 / 7.819 (1H); 7.896 (1H) ppm.

5th stage

2.4 g (6.5 mmol) of 2- [1- (3-trifluoromethylphenyl) ethylideniminoxymethyl] phenyl acetic acid chloride are cooled to a mixture of 10 ml of methanol and 0.7 g (6.9 mmol ) Triethylamine given. After 10 minutes at room temperature, the mixture is concentrated and the residue is partitioned between ethyl acetate and water. After the solvent has been stripped off, 2 g (84.3% of theory) of methyl 2- [1- (3-trifluoromethylphenyl) ethylideniminoxymethyl] phenylacetate are obtained. According to GC / MS analysis, the crude product has a content of 96.1%.
1 H-NMR spectrum (CDCI₃ / TMS):
δ = 2.238 (3H); 3,677 (3H); 3.817 (2H); 5.307 (2H); 7.241-7.33 (3H); 7.42-7.49 (2H); 7.581 / 7.607 (1H); 7.798 / 7.824 (1H); 7.899 (1H) ppm.
GC / MS analysis:
Retention index = 2198
M = 366, 365, 346, 306, l98, 163, l45, 131, 105, 78, 39.

6th stage

The preparation of this compound is in Example 5 on page 11 of EP 600 835 starting from compound (X-1).  

(Variant 2)

To 2.0 g (0.01 mol) of 3-trifluoromethylacetophenone oxime in 25 ml of dry Di Methylformamide is first added 0.3 g (0.01 mol) sodium hydride in portions (80% with mineral oil) with vigorous stirring and then 2.5 g (0.01 mol) of E-2- Methoximino-2- (2-bromomethylphenyl) acetonitrile was added.

The reaction mixture is stirred for 24 hours at 60 ° C, then to room cooled temperature, poured into water and shaken with ethyl acetate. The organic phase is washed with water, dried over sodium sulfate and in Vacuum concentrated.

3.4 g (91% of theory) of E-2-methoxirnino-2- {2- [1- (3-trifluoromethyl phenyl) -ethylideniniinoxymethyl] -phenyl} -acetonitrile as a yellow oil.

15.7 g (0.09 mol) of E-2-methoximino-2- (2-methylphenyl) acetonitrile, 16.0 g (0.09 Mol) N-bromosuccinimide and 0.45 g dibenzoyl peroxide are in 130 ml Tetrachloromethane heated to boiling under reflux overnight. Then you leave cool the reaction mixture to room temperature and filter. The mother liquor is concentrated in vacuo and the residue over silica gel (mobile solvent: Hexane / acetone 10: 1) chromatographed.

10.0 g (44% of theory) of E-2-methoximino-2- (2-bromomethylphenyl) are obtained. acetonitrile as a highly viscous oil, which was crystallized using petroleum ether becomes; Melting point = 78-79 ° C.

To a mixture of 77.2 g (0.4 mol) of E-2-methoximino-2- (2-methylphenyl) - acetamide and 171.7 g pyridine are 138.6 g (0.66 mol) at 0 ° C Trifluoroacetic anhydride added dropwise.

The mixture is stirred at 0 ° C. for 1 hour, warmed to room temperature and stirred Then the reaction mixture with 650 ml of concentrated hydrochloric acid. Then with Shaken out ethyl acetate, washed the organic phase with water, over Dried sodium sulfate and concentrated in vacuo.

69.7 g (100% of theory) of E-2-methoximino-2- (2-methylphenyl) acetonitrile are obtained.
1 H-NMR (CDCl₃): δ = 2.3 (s, 3 H).

To 120 g (0.5 mol) of E-2-methoximino-2- (2-methylphenyl) -acetic acid methyl ester in 1.5 l of methanol are given 1.5 l of 25% ammonia water and 5 hours heated under reflux. The reaction mixture is then allowed to cool, concentrated to approx. 1 l, mixed with water and shaken out with ethyl acetate. The organic phase is washed with water, dried over sodium sulfate and in vacuo constricted. The residue is stirred with diisopropyl ether, suction filtered and dried.

66.2 g (69% of theory) of E-2-methoximino-2- (2-methylphenyl) acetamide are obtained melting point 98-99 ° C.  

Example 2 (Method b)

3.5 g (0.085 mol) of E-2-methoximino-2- {2- [1- (3-trifluoromethylphenyl) ethylidenimine oxymethyl] phenyl} acetimidic acid methyl ester (Example 1) are dissolved in 30 ml of pyridine, with 0, 8 g (0.0102 mol) of acetyl chloride were added and the mixture was stirred at room temperature overnight. The solvent is concentrated, the residue is poured into water, extracted with dichloromethane, dried over sodium sulfate and concentrated again. 3.6 g of a yellow oil containing 76% (HPLC) of N-acetyl-2- (E-methoximino) -2- {2- [1- (3-trifluoromethylphenyl) ethylidene-iminoxymethyl] - are obtained. phenyl} -acetimidic acid methyl ester as a mixture of stereoisomers (ratio approx. 1: 7, not assigned).
1 H-NMR (CDCl₃): δ = 2.21; 2.26; 3.68; 3.97; 5.15; 7.15-7.95.

Example 3 (Method c)

To 2.0 g (0.005 mol) of E-2-methoximino-2- {2- [1- (3-trifluoromethylphenyl) ethylidene iminoxymethyl] -phenyl} -acetimidic acid methyl ester (example 1) and 0.2 g (0.005 mol) A solution of 3.6 g (0.01 mol) of disodium hydrogen phosphate is added to cyanamide and 1.6 g (0.01 mol) of sodium dihydrogen phosphate in 10 ml of water, as well as 10 ml Methanol and stir overnight at room temperature. The mixture is mixed with ether extracted, dried over sodium sulfate and concentrated.  

The residue is chromatographed on silica gel using cyclohexane / ethyl acetate (3: 1). 0.6 g (28%) of N-cyan-2- (E-methoximino) -2- {2- [1- (3-trifluoromethyl phenyl) ethylidene iminoxymethyl] phenyl} acetimidic acid methyl ester from the enamel point 93 ° C.

Example 4 (Method d)

To a solution of 1.1 g (0.0025 mol) of N-acetyl-2- (E-methoximino) -2- {2- [1- (3- trifluoromethylphenyl) ethylidene iminoxymethyl] phenyl) acetimidic acid methyl ester (Example 2) in 30 ml of methanol, a solution of 0.08 g (0.0025 mol) methylamine in 30 ml of tetrahydrofuran. There will be another 18 Stirred at 20 ° C for hours. The solution is concentrated and the residue is with Cyclohexane / ethyl acetate (3: 1) chromatographed on silica gel. 0.44 g (39% of theory) N-acetyl-2- (E-methoximino) -2- {2- [1- (3-trifluoromethylphenyl) ethyli den-iminoxymethyl] phenyl} acetamidine.  

Example 5 (Method e)

To a solution of 1.1 g (0.0025 mol) of N-acetyl-2- (E-methoximino) -2- {2- [1- (3- trifluoromethylphenyl) ethylidene iminoxymethyl] phenyl} acetimidic acid methyl ester (Example 2) in 30 ml of methanol is 0.08 g (0.0025 mol) of hydrazine with ice cooling given. The mixture is stirred at 20 ° C. for a further 18 hours. The solution will be concentrated and the residue with cyclohexane / ethyl acetate (3: 1) on silica gel chromatographed. 0.42 g (39% of theory) of 5-methyl-3- [E- methoximino-2- {2- [1- (3-trifluoromethylphenyl) ethylidene iminoxymethyl] phenyl} - triazole.

Example 6 (Method d)

To a solution of 1.4 g (0.0032 mol) of N-cyan-2- (E-methoximino) -2- {2- [1- (3- trifluoromethylphenyl) ethylidene iminoxymethyl] phenyl} acetimidic acid methyl ester (Example 3) in 5 ml of methanol with ice cooling 1 g (0.032 mol) of methylamine initiated. The mixture is stirred at 20 ° C. for a further 18 hours. The solution will be concentrated and the residue is cyclohexane / ethyl acetate (3: 1) on silica gel chromatographed. 0.42 g (31% of theory) of N-cyano-N'-methyl-2- (E- methoximino) -2- {2- [1- (3-trifluoromethylphenyl) ethylidene iminoxymethyl] phenyl} - acetamidine.  

Example 7 (Method e)

To a solution of 1.4 g (0.0032 mol) of N-cyan-2- (E-methoximino) -2- {2- [1- (3-tri fluoromethylpheny} ethylidene iminoxymethyl] phenyl} acetimidic acid methyl ester (Example 3) in 10 ml of methanol, while cooling with ice, becomes 0.1 g (0.0032 mol) of hydrazine given. The mixture is stirred at 20 ° C. for a further 18 hours. The solution will be concentrated and the residue with cyclohexane / ethyl acetate (3: 1) on silica gel chromatographed. 0.46 g (33% of theory) of 5-amino-3- [E- methoximino-2- {2- [1- (3-trifluoromethylphenyl) ethylidene iminoxymethyl] phenyl} - triazole.

Example 8 (Method f)

2.4 g (0.006 mol) of E-2-methoximino-2- {2- [1- (3-trifluoromethylphenyl) ethylidene iminoxymethyl] phenyl} acetimidic acid methyl ester (Example 1) are dissolved in 40 ml of 30% methylamine Solution in ethanol heated to boiling under reflux for 24 hours. The reaction mixture is then concentrated in vacuo. 2.5 g (100% of theory) of E-2-methoximino) -2- {2- [1- (3-trifluoromethylphenyl) ethylideniminoxy methyl] phenyl} acetimidic acid methylamide are obtained as an oil.
1 H-NMR (CDCI₃): δ = 2.95 (s, 3H).

Analogous to production examples 1 to 8 and in accordance with the general Description of the methods according to the invention are given in the following Compounds of the general formula (I) listed in the table are obtained:

Examples of use Example A Podosphaera test (apple) / protectiv

Solvent: 4.7 parts by weight of acetone
Emulsifier: 0.3 part by weight of alkyl aryl 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 effectiveness, young plants are sprayed with the Active ingredient preparation to dripping wet. After the spray coating has dried on the plants by dusting them with conidia of the Podosphaera powdery mildew pathogen leucotricha inoculated.

The plants are then grown in a greenhouse at 23 ° C and a relative Humidity of approx. 70% set up.

Evaluation is carried out 10 days after the inoculation.

In this test, the compound according to Preparation Example 1 shows one Active substance concentration of 20 ppm an efficiency of up to 100%.  

Example B Venturia test (apple) / protectiv

Solvent: 4.7 parts by weight of acetone
Emulsifier: 0.3 part by weight of alkyl aryl 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 effectiveness, young plants are sprayed with the Active ingredient preparation to dripping wet. After the spray coating has dried on the plants with an aqueous conidia suspension of the Venturia apple scab pathogen inoculated and then remain at 20 ° C and 100% relative for 1 day Humidity in an incubation cabin.

The plants are then grown in a greenhouse at 20 ° C and a relative Humidity of approx. 70% set up.

Evaluation is carried out 12 days after the inoculation.

In this test, the compound according to Production Example 1 shows an excellent efficiency.  

Example C Erysiphe test (barley) / protectiv

Solvent: 10 parts by weight of N-methyl-pyrrolidone
Emulsifier: 0.6 part by weight of alkyl aryl 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 effectiveness, young plants are sprayed with the Active ingredient preparation in the specified application rate. After the The plants are sprayed with spores from Erysiphe graminis f.sp. hordei pollinated.

The plants are then in the greenhouse at a temperature of about 20 ° C and a relative humidity of approx. 80% set up to the development of Favor mildew pustules.

Evaluation is carried out 7 days after the inoculation.

In this test, the compound according to Preparation Example 1 shows one Active ingredient amount of 250 g / ha an efficiency of 100%.  

Example D Erysiphe test (barley) / curative

Solvent: 10 parts by weight of N-methyl-pyrrolidone
Emulsifier: 0.6 part by weight of alkyl aryl 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 curative effectiveness, young plants with spores from Erysiphe graminis f.sp. hordei pollinated. 48 hours after inoculation Plants sprayed with the active ingredient preparation in the application rate indicated.

The plants are then in the greenhouse at a temperature of about 20 ° C and a relative humidity of approx. 80% set up to the development of Favor mildew pustules.

Evaluation is carried out 7 days after the inoculation.

In this test, the compound according to Preparation Example 1 shows one Active ingredient amount of 250g / ha an efficiency of 100%.  

Example E Erysiphe test (wheat) / protectiv

Solvent: 10 parts by weight of N-methyl-pyrrolidone
Emulsifier: 0.6 part by weight of alkyl Ary1 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 effectiveness, young plants are sprayed with the Active ingredient preparation in the specified application rate. After the The plants are sprayed with spores from Erysiphe graminis f.sp. hordei pollinated.

The plants are then in the greenhouse at a temperature of about 20 ° C and a relative humidity of approx. 80% set up to the development of Favor mildew pustules.

Evaluation is carried out 7 days after the inoculation.

In this test, the compound according to Preparation Example 1 shows one Active ingredient amount of 250 g / ha an efficiency of 100%.  

Example F Erysiphe test (wheat) / curative

Solvent: 10 parts by weight of N-methyl-pyrrolidone
Emulsifier: 0.6 part by weight of alkyl aryl 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 curative effectiveness, young plants with spores from Erysiphe graminis f.sp. hordei pollinated. 48 hours after inoculation Plants sprayed with the active ingredient preparation in the application rate indicated.

The plants are then in the greenhouse at a temperature of about 20 ° C and a relative humidity of approx. 80% set up to the development of Favor mildew pustules.

Evaluation is carried out 7 days after the inoculation.

In this test, the compound according to Preparation Example 1 shows one Active ingredient amount of 250 g / ha an efficiency of 100%.

Claims (14)

1. imidic acid derivatives of the general formula (I), in which
R represents hydrogen, cyano or the groupings -CO-R¹, -CS-R² and -S (O) _m -R³,
in which
R¹, R² and R³ each represent alkyl, alkoxy, alkylthio, amino, alkylamino or dialkylamino and
m represents the numbers 0, 1 or 2;
X represents alkoxy, alkylthio, amino, alkylamino or dialkylamino, or
X and R together with the carbon or nitrogen atom to which they are attached, for a triazole radical of the formula stand where
R⁶ represents alkyl, hydroxy, mercapto, amino, alkylamino or dialkyl amino;
Ar stands for optionally substituted arylene or heteroarylene;
G represents a single bond for oxygen, in each case alkanediyl, alkenediyl, oxaalkenediyl, alkindiyl or one of the following groups, which is optionally substituted by halogen, hydroxy, alkyl, haloalkyl or cycloalkyl: -Q-CQ-, -CQ-Q-, -CH₂- Q-; -Q-CH₂-, -CQ-Q-CH₂-, -CH₂-Q-CQ-, -Q-CQ-CH₂-, -Q-CQ-Q-CH₂-, -N = N-, -S (O ) _n -, -CH₂-S (O) _n -, -CQ-, -S (O) _n -CH₂-, -C (R⁴) = NO-, -C (R⁴) = NO-CH₂-, -QC (R⁴) = NO-CH₂, -NH-C (R⁴) = NO-CH₂-, -N (R⁵) -, -CQ-N (R⁵) -, -N (R⁵) -CQ-, -Q-CQ -N (R⁵) -, -N = C (R⁴) -Q-CH₂-, -CH₂-ON = C (R⁴) -, -N (R⁵) -CQ-Q-, -CQ-N (R⁵) - CQ-Q-, -N (R⁵) -CQ-Q-CH₂-, -CQ-CH₂- or -N = NC (R⁴) = NO-, where
Q represents oxygen or sulfur,
n represents the numbers 0, 1 or 2,
R⁴ represents hydrogen, cyano or in each case optionally substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or cycloalllyl, and
R⁵ represents hydrogen, hydroxy, cyano or in each case optionally substituted alkyl, alkoxy or cycloalkyl; and
Z represents optionally substituted alkyl, alkenyl, aldnyl, cycloalkyl, alyl or heterocyclyl;
with the exception of the compounds in which R simultaneously represents hydrogen, G represents oxygen or the group -OCH₂- and Z represents in each case optionally substituted aryl or 2-pyridyl. 2. Compounds of formula (I) according to claim 1, in which
R represents hydrogen, cyano or the groupings -CO-R¹, -CS-R² and -S (O) _m -R³,
in which
R¹, R² and R³ each represent straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 4 carbon atoms;
Amino or in each case straight-chain or branched alkylamino and dialkylamino each having 1 to 4 carbon atoms in the individual alkyl parts and
m stands for the numbers 0, 1 or 2.
X represents in each case straight-chain or branched alkoxy or alkylthio each having 1 to 4 carbon atoms;
Amino or straight-chain or branched alkylamino and dialkylamino each having 1 to 4 carbon atoms in the individual alkyl parts.
X and R together with the carbon or nitrogen atom to which they are attached, for a triazole radical of the formula stand where
R⁶ represents straight-chain or branched alkyl having 1 to 4 carbon atoms, hydroxy, mercapto, amino or in each case straight-chain or branched alkylamino and dialkylamino each having 1 to 4 carbon atoms in the individual alkyl parts.
Ar stands for optionally substituted phenylene or naphthylene or for heteroarylene with 5 or 6 ring members, at least one of which is oxygen, sulfur or nitrogen and optionally one or two more are nitrogen, the possible substituents being preferably from the list below are selected:
Halogen, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl, thio carbamoyl, each straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms, each straight-chain or branched alkenyl, alkenyloxy or alkynyloxy each 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, hydroximinoalkyl or alkoximinoalkyl each having 1 to 6 carbon atoms in the individual alkyl parts, in each case, if appropriate times or more, 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 having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, each having two times linked alkylene or Dioxyalkylene with 1 to 6 carbon atoms each.
G for a single bond, for oxygen, for in each case optionally substituted by halogen, hydroxy, C₁-C₄-alkyl, C₁-C₄-haloalkyl or C₃-C₆-cycloalkyl, alkanediyl, alkenediyl, oxaalkenediyl, alkynediyl with up to 4 carbon atoms or one of the the following groups are: -Q-CQ-, -CQ-Q-, -CH₂-Q-; -Q-CH₂-, -CQ-Q-CH₂-, -CH₂-Q-CQ-, -Q-CQ-CH₂-, -Q-CQ-Q-CH₂-, -N = N-, S (O) _n -, CH₂-S (O) _n -, -CQ-, -S (O) _n -CH₂-, -C (R⁴) = NO-, -C (R⁴) = NO-CH₂-, -QC (R⁴ ) = NO-CH₂-, -NH-C (R⁴) = NO-CH²-, -N (R⁵) -, -CQ-N (R⁵) -, -N (R⁵) -CQ-, -Q-CQ- N (R⁵) -, -N = C (R⁴) -Q-CH₂-, -CH₂-ON = C (R⁴) -, -N (R⁵) -CQ-Q-, -CQ-N (R⁵) -CQ -Q-, -N (R⁵) -CQ-Q-CH₂-, -CQ-CH₂- or -N = NC (R⁴) = N-, where
n represents the numbers 0, 1 or 2,
Q represents oxygen or sulfur,
R⁴ represents hydrogen, cyano, optionally substituted by halogen, cyano or C₁-C₄alkoxy alkyl, alkoxy, alkylthio, alkylamino or dialky1amino each having 1 to 6 carbon atoms in the alkyl groups or for each optionally substituted by halogen, cyano, carboxy, C₁ -C₄-alkyl or C₁-C₄-alkoxy-carbonyl substituted cycloalkyl having 3 to 6 carbon atoms, and
R⁵ for hydrogen, hydroxy, cyano or for optionally substituted by halogen, cyano or C₁-C₄-alkoxy-substituted alkyl having 1 to 6 carbon atoms or for optionally by halogen, cyano, carboxy, C₁-C₄-alkyl or C₁-C₄-alkoxy-carbonyl substituted cycloalkyl having 3 to 6 carbon atoms.
Z represents alkyl which is optionally substituted by halogen, cyano, hydroxy, amino, C₁-C₄alkoxy, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or C₁-C₄alkylsulfonyl (which are each optionally substituted by halogen) and is 1 to 8 Carbon atoms, for each optionally substituted by halogen alkenyl or alkynyl each having up to 8 carbon atoms, each optionally by halogen, cyano, carboxy, phenyl (which may optionally be halogen, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁ -C₄-alkoxy or C₁-C₄-haloalkoxy is substituted), C₁-C₄-alkyl or C₁-C₄-alkoxy carbonyl-substituted cycloalkyl having 3 to 6 carbon atoms, for each optionally substituted phenyl, naphthyl or (if appropriate benzene-fused) heterocyclyl with 5 or 6 ring members, at least one of which is oxygen, sulfur or nitrogen and, if appropriate, one or two more are nitrogen, the possible substituents are preferably selected from the list below:
Oxygen (as a substitute for two geminal hydrogen atoms), halogen, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl, each straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl, each with 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, halogen alkylsulfinyl 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 alkyl amino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydroximinoalkyl or alkoximinoalkyl each having 1 to 6 carbon atoms in the individual alkyl parts, in each case if appropriate singly or multiply, identically or differently, substituted 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 double-linked alkylene or dioxyalkylene each having 1 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, heterocyclyl or heterocyclyl-methyl each having 3 to 7 ring members, each of which is 1 to 3 identical or different heteroatoms - in particular nitrogen, oxygen and / or sulfur, and in each case optionally in the phenyl moiety one or more times, identically or differently, by halogen, cyano, nitro, carboxy, carbamoyl 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 are the same or different halogen atoms and / or straight-chain or branched alkoxy having 1 to 4 carbon atoms and / or straight-chain or branched halogen alkoxy with 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms and / or alkylcarbonyl or alkoxycarbonyl each having up to 5 carbon atoms substituted phenyl , Phenoxy, benzyl, benzyloxy, phenylethyl or phenylethyloxy. 3. Compounds of formula (I) according to claim 1, in which
R represents hydrogen, cyano or the groupings -CO-R¹, -CS-R² and -S (O) _m -R³,
in which
R¹ is methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl; Methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy; Methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio; Amino, methylamino, ethylamino, n- or i-propylamino; Dimethylamino, methyl-ethyl-amino, diethylamino, methyl-n- or i-propylamino and ethyl-n- or i-propylamino;
R² is methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl; Methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy; Methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio; Amino, methylamino, ethylamino, n- or i-propylamino; Dimethylamino, methyl-ethyl-amino, diethylamino, methyl-n- or i-propylamino and ethyl-n- or i-propylamino;
R³ is methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl; Methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy; Methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio; Amino, methylamino, ethylamino, n- or i-propylamino; Dimethylamino, methyl-ethyl-amino, diethylamino, methyl-n- or i-propylamino and ethyl-n- or i-propylamino; and
m stands for the numbers 0, 1 or 2.
X is methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy; Methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio; Amino, methylamino, ethylamino, n- or i-propylamino; Dimethylamino, methyl-ethyl-amino, diethylamino, methyl-n- or i-propylamino and ethyl-n- or i-propylamino.
X and R together with the carbon or nitrogen atom to which they are attached, for a triazole radical of the formula stand where
R⁶ is methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl; Hydroxy; Mercapto; Amino, methylamino, ethylamino, n- or i-propyl amino; Dimethylamino, methyl-ethyl-amino, diethylamino, methyl-n- or i-propylamino and ethyl-n- or i-propylamino.
Ar represents respectively optionally substituted ortho-, meta- or para-phenylene, furandiyl for, thiophenediyl, pyrrolediyl, pyrazolediyl, triazolediyl, oxazole diyl, Isoxazoldiyl, thiazolediyl, Isothiazoldiyl, oxadiazolediyl, thiadiazole diyl, pyridinediyl, pyrimidinediyl, pyridazinediyl, pyrazinediyl, 1, 3,4-triazine diyl or 1,2,3-triazinediyl, the possible substituents being selected in particular from the list below:
Fluorine, chlorine, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, methylthio, methylsulfinyl or methylsulfonyl.
G for a single bond, for oxygen, for methylene, dimethylene (ethane-1,2-diyl) substituted by fluorine, chlorine, hydroxyl, methyl, ethyl, n- or i-propyl, trifluoromethyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl ), Ethene-1,2-diyl, ethyne-1,2-diyl or one of the following groups -Q-CQ-, -CQ-Q-, -CH₂-Q-, -Q-CH₂-, -CQ-Q -CH₂-, -CH₂-Q-CQ-, -Q-CQ-CH₂-, -Q-CQ-Q-CH₂-, -N = N-, -S (O) _n -, -CH₂-S (O ) _n -, -CQ-, -S (O) _n -CH₂-, -C (R⁴) = NO-, -C (R⁴) = NO-CH₂-, -QC (R⁴) = NO-CH₂-, - NH-C (R⁴) = NO-CH²-, -N (R⁵) -, -CQ-N (R⁵) -, -N (R⁵) -CQ-, -Q-CQ-N (R⁵) -, -N = C (R⁴) -Q-CH₂-, -CH₂-ON = C (R⁴) -, -N (R⁵) -CQ-Q-, -CQ-N (R⁵) -CQ-Q- or -N (R⁵ ) -CQ-Q-CH₂-stands, wherein
n represents the numbers 0, 1 or 2,
Q represents oxygen or sulfur,
R⁴ represents hydrogen, cyano, methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, methoxy, ethoxy, propoxy, butoxy, methylthio, optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy, Ethylthio, propylthio, butylthio, methylamino, ethyl amino, propylamino, dimethylamino or diethylamino or for cyclopropyl, cyclobutyl, optionally substituted by fluorine, chlorine, cyano, carboxy, methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl, Cyclopentyl or cyclohexyl, and
R⁵ for hydrogen, hydroxy, cyano or for each optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or for if necessary by Fluorine, chlorine, cyano, carboxy, methyl, ethyl, n- or i-propyl, methoxy-carbonyl or ethoxy-carbonyl-substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
Z for methyl, ethyl, optionally substituted by fluorine, chlorine, bromine, cyano, hydroxyl, amino, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl (which are each optionally substituted by fluorine and / or chlorine), n- or i-propyl, n-, i-, s- or t-butyl, each for allyl, crotonyl, 1-methyl-allyl, propargyl or 1-methyl-propargyl optionally substituted by fluorine, chlorine or bromine, for each optionally by fluorine, chlorine, bromine, cyano, carboxy, phenyl (which optionally by fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl , Methoxy, ethoxy, n- or i-propoxy, difluoromoxy or trifluoromethoxy is substituted), methyl, ethyl, n- or i-propyl, methoxy-carbonyl or ethoxy-carbonyl-substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, for each optionally substituted phenyl, naphthyl, furyl, tetrahydrofuryl, benzofur yl, tetrahydropyranyl, thienyl, benzothienyl, pyrrolyl, dihydropyrrolyl, tetrahydropyrrolyl, benzopyrrolyl, benzodihydropyrrolyl, oxazolyl, benzoxazolyl, isoxazolyl, thiazolyl, benzothiazolyl, isothiazolyl, imida zololyl, pyridyl, pyrid , 3-triazinyl, 1,2,4-triazinyl or 1,3,5-triazinyl, where the possible substituents are preferably selected from the list below:
Oxygen (as a substitute for two geminal hydrogen atoms), 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, methylsifinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluoromethyl or trifluoromethyltrifluoromethyl, trifluoromethyl Trifluoromethyl sulfonyl, methylamino, ethylamino, n- or i-propylamino, dimethyl amino, diethylamino, acetyl, propionyl, acetyloxy, methoxycarbonyl, ethoxycarbonyl, methylsulfonyloxy, ethylsulfonyloxy, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl, ethoximinoethyl; trimethyl (propane-1,3-diyl), methylenedioxy or ethylenedioxy, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, as well as, in each case optionally singly or multiply, identically or differently, with fluorine, chlorine, methyl, ethyl, n- or i-propyl each optionally in the phenyl part, once or several times, identically or differently, by fluorine, chlorine, bromine, cyano, nitro, carboxy, carbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, Trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, acetyl, methoxycarbonyl or ethoxy carbonyl substituted phenyl, phenoxy, benzyl or benzyloxy. 4. Compounds of formula (I) according to claim 1, in which R represents hydrogen, cyano or the groups -CO-R¹, -CS-R² and -S (O) _m -R³, wherein
R1 is methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, amino, methylamino, ethylamino, dimethylamino or diethylamino;
R² represents methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, amino, methylamino, ethylamino, dimethylamino or diethylamino;
R³ represents methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, amino, methylamino, ethylamino, dimethylamino or diethylamino; and
m stands for the numbers 0, 1 or 2.
X represents methoxy, ethoxy, methylthio, ethylthio, amino, methylamino, ethylamino, dimethylamino or diethylamino.
X and R together with the carbon or nitrogen atom to which they are attached, for a triazole radical of the formula stand where
R⁶ represents methyl, ethyl, hydroxy, mercapto or amino.
Ar represents ortho-phenylene, pyridine-2,3-diyl or thiophene-2,3-diyl.
G represents oxygen, methylene or one of the following groups -CH₂-O-, -O-CH₂-, -S (O) _n -, -CH₂-S (O) _n -, -S (O) _n -CH₂-, -C (R⁴) = NO-, -ON = C (R⁴) -, -C (R⁴) = NO-CH₂-, -OC (R⁴) = NO-CH₂-, -NH-C (R⁴) = NO- CH₂-, -N (R⁵) - or -CH₂-ON = C (R⁴) -, where
n represents the numbers 0, 1 or 2,
R⁴ represents hydrogen, methyl or ethyl and
R⁵ represents hydrogen, methyl or ethyl.
Z stands for optionally substituted phenyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl or 1,3,5-triazinyl, the possible substituents preferably from the list below are selected:
Fluorine, chlorine, bromine, cyano, 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, difluoromethoxy, trifluoromethoxy, difluoro methylthio, trifluoromethylthio, trifluoromethylsulphinyl or Trifluorme thylsulfonyl, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl, ethoximinoethyl, in each case, where appropriate mono- or polysubstituted by identical or different Methylenedioxy or ethylenedioxy substituted by fluorine, chlorine, methyl or ethyl, and in each case optionally in the phenyl part singly or repeatedly, identically or differently by fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i- , s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy substituted phenyl, phenoxy, benzyl or benzyloxy. 5. Compounds of formula (I) according to claim 1, in which Ar stands for ortho-phenylene. 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 on pests and / or their Living space. 8. A process for the preparation of compounds of formula (I) according to claim 1, characterized in that

• a) nitriles of the general formula (II) in which
  Ar, G and Z have the meaning given in claim 1,
  with (thio) alcohols of the general formula (III) H-X¹ (III) in which
  X¹ represents alkoxy or alkylthio,
  or their alkali metal salts, if appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary;
  or
• b) the imido esters of the general formula (Ia) obtainable according to process (a) in which
  Ar, G, Z and X¹ have the meaning given above,
  with reactive acid derivatives, in particular with acid halides of the general formula (IV) Hal-R (IV) in which
  R has the meaning given above and
  Hal stands for halogen,
  or the corresponding anhydrides, if appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary;
  or
• c) the imido esters of the general formula (Ia) obtainable according to process (a) in which
  Ar, G, Z and X¹ have the meaning given above,
  with cyanamide of the formula (V) NH₂-CN (V) optionally in the presence of a diluent and, if appropriate, in the presence of a reaction auxiliary;
  or
• d) the imidic acid derivatives of the general formula (Ib) obtainable according to processes (b) and (c) in which
  Ar, G, Z and X¹ have the meaning given above and
  R ′ represents cyano or the groups -COR¹, -CSR² and -S (O) _m R³, where R¹, R², R³ and m have the meaning given above,
  with amines of the general formula (VI) H-X² (VI) in which
  X² represents amino, alkylamino or dialkylamino, optionally reacted in the presence of a diluent;
  or
• e) the imidic acid derivatives of the general formula (Ic) obtainable according to processes (b) and (c) in which
  Ar, G, Z and R ′ have the meaning given above,
  with hydrazine or hydrazine hydrate, optionally in the presence of a diluent;
  or
• f) the imido esters of the general formula (Ia) obtainable according to process (a) in which
  Ar, G, Z and X¹ have the meaning given above,
  with amines of the general formula (VI) H-X² (VI) in which
  X² has the meaning given above, optionally in the presence of a diluent.

9. Use of compounds of formula (I) according to claims 1 to 5 for Pest control. 10. Process for the preparation of pesticides, characterized characterized in that compounds of the formula (I) according to Claims 1 to 5 mixed with extenders and / or surfactants. 11. Nitriles of the formula (II) in which
Ar, Gr, and Z have the meaning given in claim 1. 12. Compounds of the formula (Ia) in which
Ar, Gr and Z have the meaning given in claim 1 and
X¹ represents alkoxy or alkylthio. 13. Compounds of formula (Ib) in which
Ar, Gr, Z and X¹ have the meaning given in claim 12 and
R 'represents cyano or the groups -COR¹, CSR² and -S (O) _m R³, where R¹, R², R³ and m have the meaning given in claim 1. 14. Compounds of formula (Ic) in which
Ar, Gr, Z and R 'have the meaning given in claim 13.