MXPA01001768A - Methoximinophenylacetic acid amides - Google Patents

Methoximinophenylacetic acid amides

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Publication number
MXPA01001768A
MXPA01001768A MXPA/A/2001/001768A MXPA01001768A MXPA01001768A MX PA01001768 A MXPA01001768 A MX PA01001768A MX PA01001768 A MXPA01001768 A MX PA01001768A MX PA01001768 A MXPA01001768 A MX PA01001768A
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Mexico
Prior art keywords
methyl
ethyl
carbon atoms
butyl
propyl
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MXPA/A/2001/001768A
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Spanish (es)
Inventor
Gerdes Peter
Gayer Herbert
Ulrich Heinemann
Berndwieland Kruger
Maulermachnik Astrid
Gerd Hanssler
Stenzel Klaus
Fritz Maurer
Robert Markert
Original Assignee
Bayer Aktiengesellschaft*
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Publication of MXPA01001768A publication Critical patent/MXPA01001768A/en

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Abstract

The invention relates to new methoximinophenylacetic acid amides of formula (I), wherein R represents alkylthio, halogenalkylthio, optionally substituted arylthio, alkoxycarbonylthio, alkylthiocarbonyl, -S-Y, -S-N(R1R2), -CO-N(R3R4), -CN, -CH2-O-R5, -PO(OR6)R7, -PS(OR6)R7 and A, O, W, Y, Z, L1-L4 and R1-R7 have the meaning given in the description. The invention also relates to a method for preparing said amides and for using them as fungicides.

Description

AMIDAS OF METOXMNOFENILACTIC ACID. FIELD OF THE INVENTION The invention relates to novel amides of methoximinophenylacetic acid, to a process for their preparation and to their use as fungicides. DESCRIPTION OF THE PRIOR ART It has already been known that certain compounds, which are similar from the point of view of their constitution to those described below, have fungicidal properties (see, for example, EP-A-398 692, EP-A-528 681, WO 97/00856). The fungicidal effect of these compounds, however, leaves much to be desired, especially at low application rates. DETAILED DESCRIPTION OF THE INVENTION The new amides of methoximinophenylacetic acid of the general formula (I) have now been found, wherein A means hydrogen, alkoxycarbonyl, methyl, ethyl or cyclopropyl, or has the same meaning as R, R means alkylthio, haloalkylthio, arylthio, optionally substituted, alkoxycarbonylthio, alkylthiocarbonyl, -SY, -SN (R'R2) , -CO-N (R3R4), -CN, -CH2-O-R5, -PO (OR6) R7, -PS (OR6) R7, where R1 signifies alkyl, Ref: 126980 R2 means alkyl, alkoxycarbonyl, or together with R1 as well as with the nitrogen atom, to which they are linked, means a substituted heterocyclic ring, R3 signifies alkyl or aryl if appropriate, R4 signifies alkylthio, alkylsulfonyl or haloalkylthio or together with R3, as well as with the nitrogen atom, with which they are bound, means a substituted heterocyclic ring if appropriate, R5 means alkyl, R6 signifies alkyl, R7 signifies alkyl, alkoxy or alkylamino, Y means same group which is already linked to the S- atom, or, when A means methyl, R also means alkylcarbonyl, alkoxycarbonyl, halogenoalkoxycarbonyl, alkoxycarbonylcarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylsulfonyl or substituted arylsulfonyl, if appropriate, G means a single bond, means Oxygen, sulfur or means alkanediyl, alkenodiyl, alkynediyl substituted In this case, halogen, hydroxy, alkyl, haloalkyl or cycloalkyl, means one of the following groupings, in which the left side is linked respectively to Z: -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 (R8) = NO-, -N (R9) -, -CQ-N (R9) - , -N (R9) -CQ-, -Q-CQ-N (R9) -, -N = C (R8) -Q-CH2-, -CH (R8) -ON = CH-, -C (R8) = NN = CH-, -NO ^ -CQ-Q-, -N (R9) -C (R8) = NO-CH2-, -O-CH2-C (R8) = NO-CH2-, -N = NC (R8) = NO-CH2-, -C (= NO-RI0) -C (R8) = NO-CH2-, _c (= NO-R10) -C (R8) -ON = CH-, -C (= NO-R10) -C (R8) = NN = CH-, -C (= NO-R10) -C (R8) -ON = C (CH3) -, -T-Ar1- or T-Ar'-Q- wherein Ar 1 means arylene, heteroarylene, cycloalkylene or heterocycloalkylene substituted if appropriate (ie a double-linked aliphatic ring, in which one or several carbon atoms are replaced by heteroatoms, ie by atoms that are different from carbon), means the numbers 0, 1 or 2, Q oxygen or sulfur, R8 means hydrogen, cyano, or means alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or cycloalkyl respectively substituted, R9 means hydrogen ene, hydroxy, cyano or means optionally substituted alkyl, alkoxy or cycloalkyl, R10 respectively means hydrogen, alkyl or benzyl substituted and T means a single bond, means oxygen, sulfur, -CH2-O-, -CH2- S- or means substituted alkanediyl, if appropriate, L1, L2, L and L4 are the same or different and independently of each other denote hydrogen, halogen or alkyl, W means hydrogen, fluorine, cyano or thiocyanate and Z means alkyl, alkenyl , substituted alkynyl, cycloalkyl, aryl or heterocyclyl, respectively, if appropriate. In the definitions the saturated or unsaturated hydrocarbon chains, such as alkyl, even in combination with heteroatoms, such as alkoxy, alkylthio, are, respectively, straight chain or branched chain. Halogenoalkyl means partially or fully halogenated alkyl. In the case of polyhalogenated haloalkyl, the halogen atoms may be the same or different. Preferred halogen atoms are fluorine and chlorine and especially fluorine. If the haloalkyl also carries other substituents, the maximum possible number of halogen atoms is reduced to the remaining free valencies. In general halogen means fluorine, chlorine, bromine or iodine, preferably means fluorine, chlorine or bromine, especially fluorine or chlorine. Heterocyclyl means saturated or unsaturated, as well as aromatic, ring compounds, in which at least one ring atom is a heteroatom, that is to say a non-carbon atom. If the ring has several heteroatoms, these may be the same or different. Preferred heteroatoms are oxygen, nitrogen or sulfur. If the ring contains several oxygen atoms, they are not contiguous. If necessary, the ring compounds form with other carbocyclic or heterocyclic, fused or bridged rings, together a polycyclic ring system. A polycyclic ring system can be linked through the heterocyclic ring or a condensed carbocyclic ring. Monocyclic or bicyclic ring systems are preferred, especially monocyclic or bicyclic, aromatic ring systems. It has also been found that the novel amines of methoxyiminophenylacetic acid of the general formula (I) are obtained if amides of the formula (II) are reacted wherein A, G, L1, L2, L3, L4, W and Z have the meanings indicated above, with an electrophilic reagent of the formula (III), RX (III) in which R has the meaning indicated above, and X means a dissociable group, if appropriate in the presence of a diluent and, if appropriate, in the presence of a base.
Finally, it has been found that the new amides of methoximinophenylacetic acid of the general formula (I) show a very potent fungicidal activity. The compounds according to the invention can optionally be present as mixtures of the various possible isomeric forms, in particular of the stereoisomers, such as, for example, the E and Z isomers or optical isomers. Both the E isomers and the Z isomers, the individual enantiomers, the racemates, as well as any mixture of these isomers are claimed. The subject of the present application are preferably methoximinophenylacetic acid amides of the formula (I), wherein A means hydrogen, methyl, ethoxycarbonyl, ethyl or cyclopropyl or has the same meaning as R, means alkylthio, haloalkylthio, alkoxycarbonylthio, alkylthiocarbonyl, with respectively 1 to 4 carbon atoms in the alkyl, phenylthio groups optionally substituted by halogen, cyano, alkyl, alkoxy or alkoxycarbonyl with 1 to 4 carbon atoms, haloalkyl or haloalkoxy with 1 to 4 carbon atoms and 1 to 9 same or different halogen atoms, -SY-, -SN (R'R2), -CO-N (R3R4), -CN, -CH2-O-R5, -PO (OR6) R7, -PS (OR6) R7. R1 means alkyl with 1 to 4 carbon atoms, R2 means alkyl with 1 to 4 carbon atoms, alkoxycarbonyl with 1 to 4 carbon atoms in the alkyl part, or together with R 1, as well as with the nitrogen atom, with which they are bound, means a heterocyclic ring with 5 or 6 members in the ring, optionally substituted by methyl or ethyl R3 means alkyl having 1 to 4 carbon atoms or phenyl optionally substituted by halogen, by alkyl or by alkoxy with 1 to 6 carbon atoms, by haloalkyl or by haloalkoxy with 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, R 4 means alkylthio or alkylsulfonyl with 1 to 4 carbon atoms or halogenalkylthio having 1 to 4 carbon atoms and 1 to 5 same or different halogen atoms or together with R 3, as well as with the atom of nitrogen, to which they are linked, means a heterocyclic ring with 5 or 6 members in the ring, optionally substituted by methyl or ethyl, R5 means alkyl with 1 to 4 carbon atoms, R6 sig it means alkyl with 1 to 4 carbon atoms, R7 means alkyl, alkoxy or alkylamino with 1 to 4 carbon atoms in the alkyl chains, Y means the same group which is already bonded to the sulfur atom, j! or, when A means methyl, R also denotes alkylcarbonyl, alkoxycarbonyl, alkoxycarbonylcarbonyl, halogenoalkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylsulfonyl with 1 to 4 carbon atoms in the alkyl or phenylsulfonyl chains optionally substituted by alkyl with 1 to 4 carbon atoms. carbon, G means a single bond, means oxygen, sulfur or means alkanediyl, alkenodiyl, alkynediyl, with respectively up to 4 carbon atoms, substituted, if appropriate by halogen, by hydroxy, by alkyl with 1 to 4 carbon atoms, halogenalkyl with 1 to 4 carbon atoms or for cycloalkyl with 3 to 6 carbon atoms means one of the following groupings, in which the left side is linked respectively with Z: -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 (R8) = NO-, -C (R8) = NO-CH2-, -N (R9) ) -, -CQ-N (R9) -, -N = N-C (R8) = N-O-CH2-, -C (= N-O-R10) -C (R8) = N-O-CH2-, -C (= NO-R10) -C (R8) -ON = CH-, -C (= NO-R10) -C (R8) = NN = CH-, -C (= NO-R10) -C ( R8) -ON = C (CH3) -, -T-Ar1- or T-Ar'-Q-, where n means the numbers 0, 1 or 2, Q means oxygen or sulfur, R8 means hydrogen, cyano, means alkyl , alkoxy, alkylthio, alkylamino or dialkylamino with respectively 1 to 6 carbon atoms in the alkyl groups, respectively substituted, if appropriate, by halogen, by cyano or by alkoxy with 1 to 4 carbon atoms, or means cycloalkyl with 3 to 6 atoms carbon atoms substituted, where appropriate, by halogen, cyano, carboxy, alkyl with 1 to 4 carbon atoms or alkoxycarbonyl with 1 to 4 carbon atoms, and R9 means hydrogen, hydroxy, cyano, or means alkyl with 1 to 6 carbon atoms optionally substituted by halogen, by cyano or by alkoxy with 1 to 4 carbon atoms, or by cycloalkyl having 3 to 6 carbon atoms, optionally substituted by halogen, by cyano, by carboxy, by alkyl having 1 to 4 carbon atoms or by alkoxycarbonyl having 1 to 4 carbon atoms, R 10 is hydrogen, alkyl having 1 to 4 carbon atoms or benzyl optionally substituted by halogen, alkyl or alkoxy respectively 1 to 6 carbon atoms, by haloalkyl or by haloalkoxy with respectively 1 to 6 carbon atoms and 1 to 13 same or different halogen atoms, T means a single bond, means oxygen, sulfur, -CH2-O-, -CH2 -S- or means alkanediyl having 1 to 3 carbon atoms, means phenylene, naphthylene, cycloalkylene respectively substituted one or more times, in the same or different forms, or means heteroarylenes or heterocycloalkylenes having 3 to 7 members in the ring, one of which being at least oxygen, sulfur or nitrogen and, if desired, one or two more nitrogen, the possible substituents being preferably chosen from the following enumeration: halogen, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl; alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl respectively straight-chain or branched chain, with respectively 1 to 6 carbon atoms, alkenyl or alkenyloxy respectively straight-chain or branched chain with respectively 2 to 6 carbon atoms; respectively straight-chain or branched halogenalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulfinyl or halogenoalkylsulfonyl having respectively 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms; halogenoalkenyl or halogenoalkenyloxy respectively straight-chain or branched chain with respectively 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms; alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydroximinoalkyl or alkoximinoalkyl, respectively straight-chain or branched chain, each having 1 to 6 carbon atoms in the individual alkyl portions, as well as; cycloalkyl with 3 to 6 carbon atoms. L1, L2, L3 and L4 are the same or different and independently of one another denote hydrogen, fluorine, chlorine, bromine, methyl, ethyl, or n- or i-propyl, n-, i-, s- or t-butyl , W means hydrogen, fluorine, cyano or thiocyanate and Z means alkyl having 1 to 8 carbon atoms, optionally substituted one or more times, in the same or different ways by halogen, cyano, hydroxy, amino, alkoxy with 1 to 4 carbon atoms, for alkylthio with 1 to 4 carbon atoms, for alkylsulfamyl with 1 to 4 carbon atoms 0 for alkylsulfonyl having 1 to 4 carbon atoms (which may be substituted, if appropriate, by halogen); means alkenyl or alkynyl with respectively up to 8 carbon atoms, respectively substituted, if appropriate, by halogen; tetrahydropyranyl; means cycloalkyl with 3 to 6 carbon atoms, each optionally substituted one or more times, in the same or different manner by halogen, by cyano, by carboxy, by phenyl (which is optionally substituted by halogen, by cyano, by alkyl with 1 to 4 carbon atoms, by halogenalkyl with 1 to 4 carbon atoms, by alkoxy with 1 to 4 carbon atoms or by halogenalkoxy with 1 to 4 carbon atoms), by alkyl with 1 to 4 carbon atoms or by alkoxycarbonyl with 1 to 4 carbon atoms; means phenyl, naphthyl, tetrahydrobenzofuran respectively substituted one or more times, in the same or different forms or means heterocyclyl with 3 to 7 members in the ring, one of which being at least oxygen, sulfur or nitrogen and in case given one or two more are nitrogen, the possible substituents being preferably chosen from the following enumeration: halogen, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl; formyl; alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl respectively straight-chain or branched chain with 1 to 6 carbon atoms respectively; substituted t-butyl tetrazole; alkenyl or alkenyloxy respectively straight-chain or branched chain with respectively 2 to 6 carbon atoms; respectively straight-chain or branched halogenalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulfinyl or halogenoalkylsulfonyl having respectively 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms; phenyl; halogenoalkenyl or halogenoalkenyloxy respectively straight-chain or branched chain with respectively 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms; alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl or alkylsulfonyloxy respectively straight-chain or branched chain with respectively 1 to 6 carbon atoms in the individual alkyl portions; alkylene or dioxyalkylene having respectively 1 to 6 carbon atoms, respectively doubly linked, each optionally substituted one or more times, in the same or different manner by halogen and / or straight-chain or branched-chain alkyl with 1 to 4 carbon atoms and / or straight chain or branched chain halogen alkyl with 1 to 4 carbon atoms and 1 to 9 same or different halogen atoms; cycloalkyl with 3 to 6 carbon atoms; heterocyclyl or heterocyclylmethyl with respectively 3 to 7 members in the ring, 1 to 3 of which, respectively, are the same or different heteroatoms -especially nitrogen, oxygen and / or sulfur-, or a group A'- \ _ j 'N O " where A means alkyl with 1 to 4 carbon atoms or cycloalkyl with 1 to 6 carbon atoms and A2 means alkyl with 1 to 4 carbon atoms, alkenyl or alkynyl with 2 to 4 carbon atoms, optionally substituted by cyano , by alkoxy, by alkylthio, by alkylamino, by dialkylamino or by phenyl. The present application relates especially to the amides of the methoximinophenylacetic acid of the formula (I), in which A means hydrogen, methyl, ethoxycarbonyl, ethyl or cyclopropyl, or has the same meaning as R, means methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, dichlorofluoromethylthio, tichloromethylthio, 2,2,2-trifluoroethylthio, 1,1-difluoroethylthio, methoxycarbonylthio, ethoxycarbonylthio, methylthiocarbonyl, ethylthiocarbonyl, n - or i-propylthiocarbonyl, phenylthio substituted, if appropriate, one to three times, fluorine, chlorine, by bromine, by cyano, by methyl, by ethyl, by n- or i-propylthio, by n-, i-, s- or t-butyl, by methoxy, by ethoxy, by n- or i-propoxy, by trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, methoxycarbonyl or ethoxycarbonyl, -SY, -SN (R! R2), -CO-N (R3R4), -CN, -CH2-O- R5, -PO (OR6) R7, -PS (OR6) R7, where R1 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, R2 means methyl, ethyl, n - or i-propyl, n-, i-, s- or t-butyl, methoxycarbonyl or ethoxycarbonyl, or together with R 1 as well as with the nitrogen atom, with which they are bound, means pyrrolidino, piperidino, or morpholino substituted in In the case given by methyl or ethyl, R3 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or phenyl, optionally substituted one to three times by fluorine, by chlorine, by bromine, by cyano, by methyl, by ethyl, by n- or i-propyl, by n-, i-, s- or t-butyl, by methoxy, by ethoxy, by n- i-propoxy, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, methoxycarbonyl or ethoxycarbonyl, R4 means methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfonyl, ethylsulphonyl, n- or i-propylsulfonyl, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, dichlorofluoromethylthio, trichloromethylthio or 2,2,2-trifluoroethylthio, or together with R3, as well as with the nitrogen atom, with which they are linked, means pyrrolidino, piperidino or morpholino, optionally substituted by methyl or ethyl, R5 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, R6 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, R7 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylamino, ethylamino, dimethylamino or diethylamino, Y means the same group that is already linked to the sulfur atom, or, when A s methyl, R means also acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, i-butoxycarbonyl, methoxycarbonylcarbonyl, 2-bromoethoxycarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methylsulfonyl, ethylsulfonyl, phenylsulfonyl or tolylsulfonyl, G stands for oxygen or means dimethylene (ethane-1,2-diyl) ), ethene-1, 2-diyl, respectively substituted, if appropriate, by fluorine, chlorine or bromine or means one of the following groupings, in which the left side is linked respectively with Z: -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 (R8) = NO-, -C (R8) = NO-CH2-, -N (R9) ) -, -CQ-N (R9) -, -NÍR CQ-, -Q-CQ-N (R9) -, -C (R8) = NN = CH-, -N (RVCQ-Q-, -CQ- NÍR ^ -CQ-Q-, -N (RYCQ-Q-CH2-, -QC (R8) = NO-CH2-, -N (R9) -C (R8) = NO-CH2-, -O-CH2- C (R8) = NO-CH2-, -N = NC (R8) = NO-CH2-, -C (= NO-R10) -C (R8) = NO-CH2-, -C (= NOR, 0) -C (R) -ON = CH-, -C (= NO-RI0) -C (R8) = NN = CH-, -C (= NO-R10) -C (R8) -ON = C (CH3) -, -T-Ar1- or T-Ar'-Q-, where n means the numbers 0, 1 or 2, Q means oxygen or sulfur, R8 means hydrogen, cyano, methyl, ethyl or cyclopropyl and R9 means hydrogen, methyl , ethyl or cyclopropyl, R10 means hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or means benzyl optionally substituted by fluorine, by chlorine, by bromine, by cyano , by methyl, by ethyl, by n- or i-propyl, by n-, i-, s- or t-butyl, by methoxy, by ethoxy, by non-propoxy, by trifluoromethyl, by trifluoroethyl, by difluoromethoxy, for trifluoromethoxy, for difluorochloromethoxy or for trifluoroethoxy, T means a single bond, means oxygen, sulfur, -CH2-O-, -CH2-S- or means substituted alkanediyl, if appropriate, Ar1 means phenylene or pyridinediyl substituted respectively given one to three times, in the same or in different forms, means pyrimidindiyl, pyridazindiyl, pyrazindiyl, 1,2,3-triazindiyl, 1,2,4-triazindiyl or 1,3,5-triazindiyl respectively monosubstituted, if any, or means 1,2,4-thiadiazoldiyl, 1,3,4-thiadiazoldiyl, 1,2,4-oxadiazoldiyl, 1,3,4-oxadiazoldiyl, the possible substituents being preferably chosen from the following enumeration: fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, cyclopropyl, methoxy, ethoxy , n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylisulfinyl, ethylsulfinyl, methylisulfonyl or ethylsulphonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethyl-sulphonyl or trifluoromethyl-sulfonyl and L1 , L2, L3 and L4 are the same or different and respectively independently of each other, hydrogen, fluorine, chlorine, bromine, methyl or ethyl, W means hydrogen, fluorine, cyano or thiocyanate, and Z means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, allyl, 2-buten-l-yl, 2- (l-methyl) -propyl, 2-methyl-2-buten-l-yl, propargyl, tetrahydropyranyl, tetrazol t-butyl substituted or means phenyl, 1,2,4-thiadiazolyl, 1,3,4- thiadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, pyridinyl, pyrimidyl, tetrahydrobenzofuranyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl or 1,3,5- triazinyl substituted, if appropriate, one to three times, in the same or in different ways, the possible substituents being preferably chosen from the following enumeration: amino, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, formyl, n- or i- propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfomyl, ethylsulphinyl, methylsulfonyl or ethylsulphonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl, methoxycarbonyl, ethoxycarbonyl, phenyl, means methylenedioxy, ethylenedioxy, respectively doubly linked, each optionally substituted by one four times, in the same or different ways by fluorine, by chlorine, by methyl, by trifluoromethyl or by ethyl, or means a grouping A1-, N O ' wherein A1 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl, or cyclobutyl and A2 means methyl, ethyl, n- or i-propyl, n-, i- , s- or t-butyl, allyl, propargyl, but-2-en-l-yl, 2-methyl-prop-l-en-3-yl, cyanomethyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methyl thiomethyl, ethylthiomethyl , methyl thioethyl, ethylthioethyl, dimethylaminomethyl, dimethylaminoethyl, methylaminomethyl, methylaminoethyl or benzyl. Independently of the definitions given above, G also means particularly preferably: oxygen or means one of the following groupings, in which the left side is linked respectively with Z: -Q-CH2-, -C (R8) = NO- CH2-, -N = C (R8) -Q-CH2-, -CH (R8, -ON = CH -, - C (R8) = NN = CH-, -C (= NO-R10) -C (R8) ) = NO-CH2-, -C (= NO-R10) -C (R8) -ON = CH-, -C (= NOR, 0) -C (R8) -NN = CH- or T-Ar'- Q- wherein R8, R9, R10, T, Ar1 and Q have the abovementioned meanings preferably, particularly preferably L1, L2, L3 and L4 independently of each other, hydrogen.
Particularly preferably, Q means oxygen. Particularly preferably, W means hydrogen. A very particularly preferred group of compounds according to the invention are those compounds of formula (I) in which A denotes hydrogen, ethoxycarbonyl, methyl or ethyl, cyclopropyl, or has the same meaning as R, R means methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, dichlorofluoromethylthio, trichloromethylthio, 2,2,2-trifluoroethylthio, 1,1-difluoroethylthio, methoxycarbonylthio, ethoxycarbonylthio, methylthiocarbonyl, ethylthiocarbonyln- or i-propylthiocarbonyl, phenylthio substituted, optionally one to three times, fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i -, s- or t-butyl, by methoxy, by ethoxy, by n- or i-propoxy, by trifluoromethyl, by trifluoroethyl, by difluoromethoxy, by trifluoromethoxy, by difluorochloromethoxy, by trifluoroethoxy, by methoxycarbonyl or by ethoxycarbonyl, -SY, -SN (R) R2), -CO-N (R3R4), -CN, -CH2-O-R5, -PO (OR6) R7, -PS (OR6) R7, where R1 >; means methyl, ethyl, n- or i-propyl, n-, i-, - s- or t-butyl, R2 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t- butyl, methoxycarbonyl or ethoxycarbonyl, or together with R 1, as well as with a nitrogen atom, with which they are bound, mean pyrrolidino, piperidino or morpholino, optionally substituted by methyl or ethyl, R 3 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or phenyl optionally substituted one to three times, fluorine, chlorine, bromine, cyano, nitro, methyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, trifluoromethyl, trifluoroethyl, difluoromethoxy by, for trifluoromethoxy, by diflúorclorometoxi for trifluoroethoxy , methoxycarbonyl or ethoxycarbonyl, R * "means methylthio, ethylthio, n- or i-propylthio, n- i-, s- or t-butylthio, metiisulfonilo, etiisulfonilo, n- or i-propylsulfonyl, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio , dichlorofl ormetiltio, trichloromethylthio or 2,2,2-triflúoretiltio, or together with R3 and with the nitrogen atom to which they are attached represent pyrrolidino, piperidino or morpholino are optionally substituted by methyl or ethyl, R5 is methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, R6 means methyl, ethyl, n- or i-propyl, n-, i, -s- or t-butyl, R7 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylamino, ethylamino, dimethylamino or diethylamino, Y means the same grouping as is bonded to the sulfur atom, or, when a is methyl, also means acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, i-butoxycarbonyl, metoxicarbonilcarbonilo, 2-bromoethoxycarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, metiisulfonilo, etiisulfonilo, phenylsulfonyl or tolylsulfonyl, G represents oxygen or especially -O-CH2-, L1, L2, L3 and L4 mean hydrogen, W means hydrogen, fluorine, cy ano or thiocyanate, and Z means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, allyl, 2-buten-l-yl, 2-methyl-2-buten-l -yl, propargyl, tetrahydropyranyl or means phenyl, each optionally substituted one to three times, in the same or in different ways, the possible substituents being preferably chosen from the following enumeration: 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, metiisulfinilo, ethylsulfinyl, metiisulfonilo or etiisulfonilo, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoro-ethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethyl-sulphonyl or trifluoromethylsulfonyl, methoxycarbonyl, ethoxycarbonyl, phenyl, methylenedioxy or ethylenedioxy respectively doubly linked, each optionally substituted one to four times, in the same or in the same way different by flú or, by chlorine, by methyl, by trifluoromethyl or by ethyl or a grouping A 'AV. ^ N O where A 1 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl or cyclobutyl and A2 means methyl, ethyl, n- or i-propyl, n-, i- , s- or t-butyl, allyl, propargyl, but-2-en-l-yl, 2-methyl-prop-l-en-3-yl, cyanomethyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, methylthioethyl, ethylthioethyl, dimethylaminomethyl, dimethylaminoethyl, methylaminomethyl, methylaminoethyl or benzyl. A particularly preferred group of compounds according to the invention are those compounds of the formula (I), in which A denotes hydrogen, ethyl or methyl, or has the same meaning as R, R means methylthio, ethylthio, n- or i- propylthio, n-, i-, s- or t-butylthio, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, dichlorofluoromethylthio, trichloromethylthio, 2,2,2-trifluoroethylthio, methoxycarbonylthio, ethoxycarbonylthio, methylthiocarbonyl, ethylthiocarbonyl, n- or i-propylthiocarbonyl, phenylthio substituted, optionally one to three times, fluorine, chlorine, bromine, cyano, methyl, ethyl, by n- or i-propyl, by n-, i-, s- or t-butyl, by methoxy, by ethoxy, by n- or i-propoxy, by trifluoromethyl, by trifluoroethyl, by difluoromethoxy, by trifluoromethoxy, by difluorochloromethoxy, by trifluoroethoxy, by methoxycarbonyl or by ethoxycarbonyl, -SY, -SN (R'R2), -CO-N (R3R4), -CN, -CH2-O-R5, -POIOR ^ R7, -PS (OR6 R7, where R1 signifies methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, R2 means methyl, ethyl, n- or i-propyl, n-, i-, s - or t-butyl, methoxycarbonyl or ethoxycarbonyl, or together with R 1, as well as with the nitrogen atom, to which they are linked, means pyrrolidino, piperidino or morpholino, optionally substituted by methyl or ethyl, R 3 means methyl, ethyl , n- or i-propyl, n-, i-, s- or t-butyl or, phenyl optionally substituted one to three times by fluorine, by chlorine, by bromine, by cyano, by methyl, by ethyl, by n- or i-propyl, by n-, i-, s- or t- butyl, by methoxy, by ethoxy, by n- or i-propoxy, by trifluoromethyl, by trifluoroethyl, by difluoromethoxy, by trifluoromethoxy, by difluorochloromethoxy, by trifluoroethoxy, by methoxycarbonyl or by ethoxycarbonyl, R4 means methylthio, ethylthio, n- or -propylthio, n-, i-, s- or t-butylthio, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, dichlorofluoromethylthio, trichloromethylthio, or 2,2,2-trifluoroethylthio, or together with R3 , as well as with the nitrogen atom, to which they are linked, means pyrrolidino, piperidino or morpholino, optionally substituted by methyl or ethyl, R5 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, R6 means methyl, ethyl, n- or i-propyl, n-, i, -s- or t-butyl, R7 means methyl, ethyl, n- or i-propyl, n -, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylamino, ethylamino, dimethylamino or diethylamino, Y means the same group that is already bonded to the sulfur atom, or, when A means methyl, also means acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methoxycarbonylcarbonyl, 2-bromoethoxycarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methylsulfonyl, ethylsulfonyl, phenylsulfonyl or tolylsulfonyl.
G means -C (R8) = NO-CH2, R8 means cyclopropyl or especially methyl, L1, L2, L3 and L4 mean hydrogen, W means hydrogen, fluorine, cyano or thiocyanate and Z means methyl, ethyl, n- or i- propyl, n-, i-, s- or t-butyl, allyl, 2-buten-1-yl, 2-methyl-2-buten-1-yl, propargyl, or means pyridyl, pyrimidyl, or, especially substituted phenyl respectively, optionally from one to three times, in the same or in different ways, the possible substituents being preferably chosen as follows: 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, methylisulfinyl, ethylsulfyl, methylsulfonyl or ethylsulfonyl, Trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, diflúorclorometoxi, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl, methoxycarbonyl, ethoxycarbonyl, metoximinometilo, etoximinometilo, metoximinoetilo, etoximinoetilo, methylenedioxy or ethylenedioxy respectively doubly attached each substituted optionally one to four times, in the same or different ways by fluorine, by chlorine, by methyl, by trifluoromethyl or by ethyl. Another especially preferred group of compounds according to the invention are those compounds of the formula (I), in which A means hydrogen, ethyl or methyl, or has the same meaning as R, R means methylthio, ethylthio, n- or i-propylthio , n-, i-, s- or t-butylthio, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, dichlorofluoromethylthio, trichloromethylthio, 2,2,2-trifluoroethylthio, methoxycarbonylthio, ethoxycarbonylthio, methylthiocarbonyl, ethylthiocarbonyl, n- or i-propylthiocarbonyl, phenylthio substituted in case given from one to three times, by fluorine, by chlorine, by bromine, by cyano, by methyl, by ethyl, by n- or i-propyl, by n-, i-, s- or t-butyl, by methoxy , by ethoxy, by non-propoxy, by trifluoromethyl, by trifluoroethyl, by difluoromethoxy, by trifluoromethoxy, by difluorochloromethoxy, by trifluoroethoxy, by methoxycarbonyl or by ethoxycarbonyl, -SY, -SN (R'R2), -CO-N ( R3R4), -CN, -CH2-O-R5, -PO (OR6) R7, -PS (OR6) R7, where R1 signifies methyl, ethyl, n- or i-pro pilo, n-, i-, s- or t-butyl, R2 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxycarbonyl or ethoxycarbonyl, or together with R1, as well as with the nitrogen atom, to which they are linked, means pyrrolidino, piperidino or morpholino, optionally substituted by methyl or ethyl, R3 means methyl, ethyl, n- or i-propyl, n-, i-, s - or t-butyl or phenyl optionally substituted one to three times, fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, by methoxy, by ethoxy, by n- or i-propoxy, by trifluoromethyl, by trifluoroethyl, by difluoromethoxy, by trifluoromethoxy, by difluorochloromethoxy, by trifluoroethoxy, by methoxycarbonyl or by ethoxycarbonyl, R4 means methylthio, ethylthio n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfonyl, ethylsulphonyl, n- or i-propylsulfonyl, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, dichlorofluoromethylthio, trichloromethylthio or 2,2,2-tri Fluoroethylthio, or together with R 3, as well as with the nitrogen atom, with which they are bound, means pyrrolidino, piperidino or morpholino, optionally substituted by methyl or ethyl, R 5 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, R6 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, R7 means methyl, ethyl, n- or i- propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylamino, ethylamino, dimethylamino or diethylamino, Y means the same group that is already bonded to the sulfur atom, or when A means methyl, R also means acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methoxycarbonylcarbonyl, 2-bromoethoxycarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methylsulfonyl, ethylsulfonyl, phenylsulfonyl or tolylsulfonyl, G means -T-Ar'-O, Ar1 means 1,2 4-thiadiazoldiyl, 1, 3,4-thiadiazoldiyl, 1,2,4-oxadiazoldiyl, 1,3,4-oxadiazoldiyl or means pyridindiyl, pyrimidindiyl or 1,3, 5-triazindiyl, each optionally substituted one or two times, in the same or different manner by fluorine, by chlorine, by cyano, by methyl, by cyclopropyl, by methoxy, by methylthio, by trifluoromethyl, by difluoromethoxy, by trifluoromethoxy, by difluorochloromethoxy, T means a single bond, means oxygen, sulfur, -CH2-O-, CH2-S-, methylene, ethylene or propylene and L1, L2, L3 and L4 mean hydrogen, W means hydrogen, fluorine, cyano or thiocyanate and Z means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, allyl, 2-buten-l-yl, 2- (1-methyl) -propyl, 2-methyl-2-buten-1-yl, propargyl or means pyridyl, pyrimidyl, thienyl, tetrahydrobenzofuranyl or especially phenyl, each optionally substituted one to three times, in the same or in different forms by amino, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, formyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, for trifluoromethyl, for substituted t-butyl tetrazole, for methoxy, for ethoxy, for n- or i-propoxy, for difluoromethoxy, for difluorochloromethoxy, for trifluoroethoxy, for trifluoromethoxy, for methoximinomethyl, for ethoximinoethyl, for methoximinoethyl, by ethoxymethyl or methylenedioxy or ethylenedioxy respectively double-bonded, respectively optionally substituted one to four times, in the same or different ways by fluorine, chlorine, methyl, trifluoromethyl or ethyl. In addition, another particularly preferred group of compounds according to the invention are those compounds of the formula (I), in which A means hydrogen or methyl, or has the same meaning as R, R means methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, dichlorofluoromethylthio, trichloromethylthio, 2,2,2-trifluoroethylthio, methoxycarbonylthio, ethoxycarbonylthio, methylthiocarbonyl, ethylthiocarbonyl, n- or i-propylthiocarbonyl, phenylthio substituted, optionally, one to three times fluorine, chlorine, bromine, cyano, methyl or ethyl , by n- or i-propyl, by n-, i-, s- or t-butyl, by methoxy, by ethoxy, by n- or i-propoxy, by trifluoromethyl, by trifluoroethyl, by difluoromethoxy, by trifluoromethoxy, by difluorochloromethoxy, by trifluoroethoxy by methoxycarbonyl or by ethoxycarbonyl, -SY, -SN (R'R2), -CO-N (R3R4), - CN, -CH2-O-R5, -PO (OR6) R7, -PS (OR6) R7, where R1 signifies methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, R2 means methyl, ethyl, n- or i-propyl, n-, i-, s - or t-butyl, methoxycarbonyl or ethoxycarbonyl, or together with R 1, as well as with the nitrogen atom, to which they are linked, means pyrrolidino, piperidino, morpholino, optionally substituted by methyl or ethyl, R 3 means methyl, ethyl , n- or i-propyl, n-, i-, s- or t-butyl or fe nyl, optionally substituted one to three times, fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl by methoxy, by ethoxy, by n- or i-propoxy, by trifluoromethyl, by trifluoroethyl, by difluoromethoxy, by trifluoromethoxy, by difluorochloromethoxy, by trifluoroethoxy, by methoxycarbonyl or by ethoxycarbonyl, R4 means methylthio, ethylthio, n- or i- propylthio, n-, i-, s- or t-butylthio, methylsulfonyl, ethylsulphonyl, n- or i-propylsulphonyl, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, dichlorofluoromethylthio, trichloromethylthio or 2,2,2-trifluoroethylthio, or together with R3, as with the nitrogen atom, with which they are bound, it means pyrrolidino, piperidino, or morpholino, optionally substituted by methyl or by ethyl, R5 means methyl, ethyl, n- or i-propyl, n-, i-, s - or t-butyl, R6 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, R7 means methyl, ethyl, n- or i-propyl, n-, i- , s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylamino, ethylamino, dimethylamino, or diethylamino, Y means the same group that is bonded to the sulfur atom, or, when A means methyl, R means also acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methoxycarbonylcarbonyl, 2-bromoethoxycarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methylsulfonyl, ethylsulfonyl, phenylsulfonyl, or tolylsulfonyl, G stands for -C (= NO-R10) -C (R8) = NO-CH2- where R8 means methyl or cyclopropyl and R10 means hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or means benzyl optionally substituted by fluorine, by chlorine, by bromine, by cyano , by methyl, by ethyl, by n- or i-propyl, by n-, i-, s- or t-butylby methoxy, by ethoxy, by n- or i-propoxy, by trifluoromethyl, by trifluoroethyl, by difluoromethoxy, by trifluoromethoxy, by difluorochloromethoxy or by trifluoroethoxy, L1, L2, L3 and L4 mean hydrogen, W means hydrogen, cyano or thiocyanate and Z means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, allyl, 2-buten-1-yl, 2-methyl-2-buten-1-yl or means pyridyl, pyrimidyl or especially phenyl, each optionally substituted one to three times, in the same or in different ways, the possible substituents being preferably chosen from the following enumeration: fluorine, chlorine, bromine, cyano, methyl, ethyl, n- i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl , difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluo rmethylsulfmyl or trifluoromethylsulphonyl, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, ethoximinomethyl, methoxymethyl, ethoxymethyl, methylenedioxy, ethylenedioxy, respectively double-bonded, respectively substituted one to four times, in the same or different ways by fluorine, by chlorine, by methyl, by trifluoromethyl or by ethyl, or substituted tetra-t-butyl. Particularly preferred are the compounds of the formula (I), in which A means methyl. Especially preferred are compounds of the formula (I), in which G is oxygen, -O-CH 2, -C (CH 3) = N-O-CH 2 - or pyrimidinyloxy optionally substituted by fluorine. Particularly preferred are compounds of the formula (I), in which Z means unsubstituted or mono- or disubstituted phenyl. Particularly preferred are the compounds of the formula (I) in which R denotes the abovementioned substituents, bonded through sulfur, such as especially alkyl-, haloalkyl-, phenyl-, optionally substituted, alkoxycarbonyl- or dialkylamino-thio . Particularly preferred are compounds of the formula (I), in which W denotes hydrogen.
Especially preferred are compounds of the formula (I), in which L 1, L 2, L 3 and L 4 are hydrogen. The definitions of the residues indicated above in a general manner or indicated in the preferred ranges are valid both for the final products of the formula (I) and also, correspondingly, for the starting products or for the intermediate products necessary respectively for obtaining. The definitions of the residues can be combined arbitrarily with each other, that is to say even between the indicated ranges of the preferred compounds. The amides, which are necessary as starting materials for carrying out the process according to the invention for the preparation of the methoxyiminophenylacetic acid amides of the formula (I), are generally defined by the formula (II). In this formula (II) A, G, L1, L2, L3, L4, W and Z preferably have or especially those meanings which have already been mentioned above, preferably or particularly preferably for A, G, L1, L2 , L3, L4, W and Z in relation to the description of the compounds according to the invention of the formula (I). The amides of the formula (I) are known and can be prepared according to known methods (see, for example, EP-A-398 692, EP-A-528 681, WO 98/21 189). The electrophilic reagents, which are also necessary as starting materials for carrying out the process according to the invention for the preparation of the methoximinophenylacetic acid amides of the formula (I), are defined by the formula (I). X means a dissociable group, such as, for example, halogen, preferably chlorine. When R means alkylcarbonyl, carboxylic acid anhydrides will also be considered as compounds of the formula (III), that is to say that R means -CO-R ', where R' signifies alkyl, preferably methyl or ethyl. When R means alkylaminocarbonyl, the corresponding isocyanates will also be considered as reactants of the formula (III). All the reagents of the formula (III) are chemical products for known synthesis and the person skilled in the art knows perfectly well which reagent is considered in each particular case. Suitable diluents for carrying out the process according to the invention are all inert organic solvents. These preferably include aliphatic, alicyclic or aromatic hydrocarbons, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin, halogenated hydrocarbons, such as, for example, chlorobenzene, dichlorobenzene, dichloromethane, chloroform, tetrachloromethane, dichloroethane, or trichloroethane, ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane, or anisole; ketones such as acetone, butanone, methyl isobutyl ketone or cyclohexanone; nitriles such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile, amides, such as N, N-dimethylformamide, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphorotriamide; esters such as methyl acetate or ethyl acetate; sulfoxides such as dimethisulfoxide, sulfones, such as sulfolane; or alcohols, just as you do. -butanol. The process according to the invention is carried out, if appropriate, in the presence of a suitable acid acceptor. As such, all usual inorganic or organic bases are suitable. These preferably include hydrides, hydroxides, amides, alcoholates, carbonates or bicarbonates of alkaline earth metals or alkali metals, such as, for example, sodium hydride, potassium hydride, sodium amide, potassium tert-butylate, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, potassium bicarbonate or sodium bicarbonate, as well as tertiary amines, such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, N, N-dimethylbenzylamine, pyridine, N -methylpiperidine, N-methylmorpholine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU). The reaction temperatures in carrying out the process according to the invention can vary within wide limits. In general, work is carried out at temperatures of -100 ° C to 80 ° C, preferably at temperatures of -80 ° C to 50 ° C. To carry out the process according to the invention for the preparation of the compounds of the formula (I), generally 1 to 3 moles, preferably 1 to 2 moles, are used per mole of the amide of the formula (I). of the electrophilic reagent of the formula (III). The conduct of the reaction, the preparation and the isolation of the products of the reaction are carried out according to customary methods (see also the preparation examples). The products according to the invention have a powerful microbicidal effect and can be used in practice to combat undesired micro-organisms, such as fungi and bacteria, in the protection of plants and in the protection of materials. Fungicidal agents are used in the protection of plants for the fight against plasmodioforomycetes, oomycetes, chytridiomycetes, zygomycetes, ascomycetes, basidiomycetes, deuteromycetes. Bactericidal agents are used in the protection of plants to combat pseudomonadaceos, rhizobiaceous, enterobacteriaceous, corynebacteriaceous and streptomycete. Some pathogens of fungal and bacterial diseases, which fall within the general definitions listed above, may be mentioned by way of example, but without any limiting character: types of xanthomonas, such as, for example, Xanthomonas campestris pv. oryzae; pseudomonas types, such as, for example, Pseudomonas syringae pv. lachrymans; types of erwinia, such as for example Erwinia amylovora; types of pitium, such as for example Pythium ultimun; phytophthora types, such as for example Phytophthora infestans; pseudoperonospora types, such as, for example, Pseudoperonospora humuli or Pseudoperonospora cubensis; types of plasmopara, such as for example Plasmopara viticola; types of bremia, such as for example Bremia lactucae; types of peronospora, such as, for example, Peronospora pisi or P. brassicae; types of erisife, such as for example Erysiphe graminis; types of sphaerotheca, such as for example Sphaerotheca fuliginea; types of podosfaera, such as for example Podosphaera leucotricha; types of venturia, such as, for example, Venturia inaequalis; Pyrenophora species, such as, for example, Pyrenophora teres or P. gramínea; (form of conidia, Drechslera, synonym: Helminthosporium); types of cocliobolus, such as for example Cochliobolus sativus (conideas form, Drechslera, synonym: Henminthosporium); types of uromices, such as, for example, Uromyces appendiculatus; types of pucinia, such as for example Puccinia recondita; Types of sclerotinia, such as for example Sclerotinia sclerotiorum; types of tilletia, such as for example Tilletia caries; types of ustylago, such as, for example, Ustilago nuda or Ustilago avenae; types of pelicularia, such as for example Pellicularia sasakii; blasting types, such as, for example, Pyricularia oryzae; fusarium types, such as, for example, Fusarium culmorum; Botrytis types, such as, for example, Botrytis cinerea; Septoria types, such as, for example, Septoria nodorum; types of leptosphaeria, such as for example Leptosphaeria nodorum; types of cercospora, such as for example Cercospora canescens; alternating types, such as, for example, Alternaria brassicae; types of pseudocercosporela, such as, for example, Pseudocercosporella herpotrichoides. The good compatibility with plants and active products at the concentrations necessary for the fight against plant diseases allows a treatment of the aerial parts of the plants, of seedlings and seeds and of the soil. In this case, the active compounds according to the invention will be used with particularly good success in the control of cereal diseases, such as, for example, against Erysiphe types, Puccinia or Fusarium types, diseases in culture crops. vines, fruit trees and vegetables, such as, for example, against types of Venturia, Sphaerotheca Podosphaera and Plasmopara, or rice diseases, such as, for example, Pyricularia types. In addition, the compounds according to the invention can be used to increase harvesting of the crops. They are also of low toxicity and have good compatibility with plants. The active products will be transformed, depending on their respective physical and / or chemical properties, into the usual formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granulates, aerosols, microencapsulated in polymeric materials and in coating compositions. for seeds, as well as ultra-low volume cold and hot fog (ULV) formulations. These formulations are prepared in known manner, for example by mixing the active compounds with extenders, that is, with liquid solvents, liquefied gases under pressure and / or solid excipients, optionally with the use of surfactants, ie emulsifiers and / or dispersants and / or foam generating means. When water is used as an extender, organic solvents can be used, for example, as auxiliary solvents. Preferred liquid solvents are: aromatic hydrocarbons, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatic hydrocarbons and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, alcohols such as butanol, or glycol, as well as their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, or strongly polar solvents, such as dimethylformamide and dimethyl sulfoxide as well as water; liquefied gaseous excipients or excipients are those liquids which are gaseous at normal temperature and pressure, for example propellant gases for aerosols, such as halogenated hydrocarbons, as well as butane, propane, nitrogen and carbon dioxide; as solid excipients, the ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and the synthetic molten minerals, such as highly dispersed silicic acid, aluminum oxide and silicates; as solid excipients for granulates, broken and fractionated natural minerals, such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic flours and granulates of organic material, such as sawdust, walnut shells, can be used of coconut, corn ears and tobacco stems; suitable emulsifiers and / or foamers are, for example, non-ionogenic and anionic emulsifiers, such as polyoxyethylenated esters of fatty acids, polyoxyethylenated esters of fatty alcohols, for example, alkylaryl polyglycol ether, alkylsulfonates, alkyl sulphates, Aryl sulfonates as well as albumin hydrolysates; Dispersants include sulfite lignin bleach and methylcellulose. Adhesives, such as carboxymethylcellulose and natural and synthetic polymers powdery, granulated or in the form of latex, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as phospholipids, such as cephalin and lecithin and synthetic phospholipids can be used in the formulations. . Other additives can be mineral or vegetable oils. Dyes, such as inorganic pigments, for example, iron oxide, Prussian blue titanium oxide and organic dyes, such as metallic alizarin, azo and phthalocyanine dyes as well as trace nutrients, such as iron, manganese salts, boron, copper, cobalt, molybdenum and cmc. The formulations contain, in general, between 0.1 and 95% by weight, preferably between 0.5 and 90% of active product. The active products will be transformed, depending on their respective physical and / or chemical properties, into the usual formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granulates, aerosols, microencapsulated in polymeric materials and in coating compositions. for seeds, as well as ultra-low volume cold and hot fog (ULV) formulations. The active compounds according to the invention can be used as such or in their formulations even in admixture with cone fungicides, bactericides, acaricides, nematicides or insecticides to expand the spectrum of activity or to overcome resistance developments. In many cases synergistic effects are obtained in this way, that is to say that the activity of the mixture is greater than the activities of the individual components. The following compounds are suitable as the mixing components: Fungicides: Aldimorph, Ampropylfos, Ampropylfos-potassium, Andoprim, Anilazin, Azaconazole, Azoxystrobin, Benalaxyl, Bonodanil, Benomyl, Benzamacril, Benzamacryl-isobutyl, Bialaphos, Binapacryl, Biphenyl, Bitertanol, Blasticidin -S, Bromuconazole, Bupirimat, Buthiobat, Calcium Polysulfide, Capsimycin, Captafol, Captan, Carbendazim, Carboxin, Carvon, Chinomethionat (Quinomethionat), Chlobenthiazon, Chlorfenazole, Chloroneb, Chloropicrin, Chlorothalonil, Chlozolinat, Clozylacon, Cufraneb, Cymoxanil, Cyproconazole, Cyprodinil, Cyprofuram, Debacarb, Dichlorophen, Diclobutrazol, Diclofluanid, Diclomezin, Dicloran, Diethofencarb, Difenoconazole, Dimethirimol, Dimethomo h, Diniconazole, Diniconazole-M, Dinocap, Diphenylamin, Dipyrithione, Ditalimphos, Dithianon, Dodemorph, Dodine, Drazoxolon, Ediphenphos, Epoxiconazole , Etaconazole, Ethyrimol, Etriadiazole, Famoxadon, Fenapanil, Fenarimol, Fenbuconazole, Fenfuram, Fenitrop an, Fenpiclonil, Fenpropidin, Fenpropimofh, Fentinacetat, Fentinhidroxyd, Ferbam, Ferimzon, Fluazinam, Flumetover, Fluoromid, Fluquinconazole, Flufrimidol, Flusilazol, Flusulfamid, Flutolanil, Flutriafol, Folpet, Fosetyl-aluminum, Fosetyl-sodium, Fthalid, Fuberidazole, Furalaxyl, Furametpyr, Furcarbonil, Furconazol, Furconazol-cis, Fumercyclox, Guazatin, hexachlorobenzene, Hexaconazole, Hymexazole, Imazalil, Imibenconazole, Iminoctadin, Iminoctadinealbesilat, Iminoctadinetriacetat, Iodocarb, Ipconazole, Iprobenfos (PPI), Iprodione, Irumamycin, Isoprothiolan, Isovaledione, Kasugamycin, Kresoxim -methyl, copper preparation, such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, copper oxine and Bordeaux mixture, Mancopper, Mancozeb, Maneb, Meferimzone, Mepanipyrim, Mepromil, Metalaxyl, Metconazole, Methasulfocarb, Methfuroxam, Metiram, Metomeclam, Metsulfovax, Mildiomycin, Myclobutanil, Myclozolin, Nickel dimethyldithiocarbamate, Nitr othal-isopropyl, Nuarimol, Ofurace, Oxadixyl, Oxamocarb, Oxolinicacid, Oxycarboxim, Oxyfenthiin, Paclobutrazol, Pefurazoat, Penconazol, Pencycuron, Phosdiphen, Pimaricin, Piperalin, Polyoxin, Polyoxorim, Probenazole, Prochloraz, Procymidon, Propamocarb, Propanosine-sodium, Propiconazole, Propineb, Pyrazophos, Pyrifenox, Pyrimethanil, pyroquilon, Pyroxyf r, quinconazole, Quintozen (PCNB), sulfur and sulfur preparations, tebuconazole, tecloftalam, Tecnazen, Tetcyclacis, tetraconazole, thiabendazole, Thicyofen, Thifluzamide, Tthiophanate-methyl, Thiram, Thioxymid, Tolclofos-methyl, Tolylfluanid, triadimefon, triadimenol, triazbutil, Triazoxid, Trichlamid, Tricyclazol, Tridemofh, Triflumizole, Triforin, triticonazole, uniconazole, Validamycin A, vinclozolin, viniconazole, zarilamid, zineb, Zira and Dagger G, OK-8705, OK-8801, to - (1,1-dimethylethyl) -β- (2-phenoxyethyl) -1 H- 1,2,4-triazole-1-ethanol, a- (2,4-dichlorophenyl) -β-fluoro-b-propyl- lH-L, 2,4-triazole-1-ethanol, a- (2,4-dichlorophenyl) -β-methoxy-α-methyl-1H-1, 2,4-triazole-1-ethanol, - (5- methyl-l, 3-dioxan-5-yl) -β - [[4- (trifluoromethyl) -phenyl] -methylene] -lH-l, 2,4-triazole-l-ethanol, (5RS, 6RS) -6 -hydroxy-2,2,7,7-tetramethyl-5- (lH-1, 2,4-triazol-1-yl) -3-octanone, (E) -a- (methoxyimino) -N-methyl-2 -phenoxy-phenylacetamide,. { 2-methyl-1 - [[[1- (4-methylphenyl) -ethyl] -amino] -carbonyl] -propyl} 1-isopropyl carbamate, 1- (2,4-dichlorophenyl) -2- (1H-1,2,4-triazol-1-yl) -ethanon-O- (phenylmethyl) -oxime, 1- (2 -methyl-1-naphthalenyl) - lH-pyrrole-2, 5-dione, 1- (3,5-dichlorophenyl) -3- (2-propenyl) -2,5-pyrrolidinedione, 1 - [(diy odomethyl) - sulfonyl] -4-methyl-benzene, l - [[2- (2,4-dichlorophenyl) -l, 3-dioxolan-2-yl] -methyl] -lH-imidazole, l - [[2- (4- chlorophenyl) -3-phenyloxyranyl] -methyl] -lH-1, 2,4-triazole, 1 - [1 - [2- [(2,4-dichlorophenyl) -methoxy] -phenyl] -ethenyl] -1H- imidazole, 1-methyl-5-nonyl-2- (phenylmethyl) -3-pyrrolidinol, 2 ', 6'-dibromo-2-methyl-4'-tr iflúormetoxi-4'-methyl- -triflúor 1, 3-thiazole -5-carboxanilide, 2,2-dichloro-N- [1- (4-chlorophenyl) -ethyl] -1-ethyl-3-methyl-cyclopropanecarboxamide, 2,6-dichloro-5- (methylthio) -4 pyrimidinyl thiocyanate, 2, 6-dichloro-N- (4-trifluoromethylbenzyl) -benzamide, 2, 6-dichloro-N- [[4- (iflúormetil tr) -phenyl] -methyl] -benzamide, 2- (2 , 3,3-triiodo-2-prope-nyl) -2H-tetrazole, 2 - [(1-methylethyl) -sulfonyl] -5- (trichloromethyl) -1,3,4-t iadiazole, 2 - [[6-deoxy-4-O- (4-O-methyl-β-D-glycopyranosyl) -aD-glucopyranosyl] -amino] -4-methoxy-1H-pyrrolo [2, 3-d ] pyrimidine-5-car-bonitrile, 2-aminobutane, 2-bromo-2- (bromomethyl) -pentandinitrile, 2-chloro-N- (2,3-dihydro-l, 1,3-trimethyl-lH-inden- 4-yl) -3-pyridinecarboxamide, 2-chloro-N- (2,6-dimethylphenyl) -N- (isothiocyanatomethyl) -acetamide, 2-phenylphenol (OPP), 3,4-dichloro- 1 - [4- ( difluoromethoxy) -phenyl] -1H-pyrrole-2, -di-one, 3,5-dichloro-N- [cyan [(1-methyl-2-propynyl) -oxy] -methyl] -benzamide, 3- ( l, 1-dimethylpropyl) -l-oxo-lH-inden-2-carbonitrile, 3- [2- (4-chlorophenyl) -5-ethoxy-3-isoxazolidinyl] -pyridine, 4-chloro-2-cyan-N , N-dimethyl-5- (4-methylphenyl) -lH-imidazole-1-sulfonamide, 4-methyl-tetrazolo [1, 5-a] quinazolin-5 (4H) -one, 8- (1, 1-dimethylethyl) ) -N-ethyl-N-propyl-l, 4-dioxaspiro [4,5] decan-2-methanamine, 8-hidroxiquinolinsulfato, 2 - [(phenylamino) carbonyl] hydrazide 9H-xanthene acid-9-carboxylic acid , bis- (1-methylethyl) -3-methyl-4 - [(3-methylbenzoyl) -oxy] -2,5-thiophenecarboxylate, cis- 1 - (4-chlorophenyl) -2- (1 H- 1,2,4-triazol-1-yl) -cycloheptanol, cis-4- [3- [4- (1, 1-dimethylpropyl) -phenyl-2-hydrochloride. methylpropyl] -2,6-dimethyl-morpholine, ethyl - [(4-chlorophenyl) azo] -cianoacetato, potassium bicarbonate, sodium salt Methantetrathiol-methyl- 1 - (2, 3-dihydro-2, 2- dimethyl-1 H-inden-1-yl) -1 H-imidazole-5-carboxylate, methyl-N- (2,6-dimethylphenyl) -N- (5-isoxazolylcarbonyl) -DL-alaninate, methyl-N- ( chloroacetyl) -N- (2,6-dimethylphenyl) -DL-alaninate, N- (2,3-dichloro-4-hydroxyphenyl) -l-methyl-cyclohexanecarboxamide, N- (2,6-dimethylphenyl) -2-methoxy -N- (tetrahydro-2-oxo-3-furanyl) -acetamide, N- (2,6-dimethylphenyl) -2-methoxy-N- (tetrahydro-2-oxo-3-thienyl) -acetamide, N- ( 2-chloro-4-nitrophenyl) -4-methyl-3-nitro-benzenesulfonamide, N- (4-cyclohexylphenyl) -l, 4,5,6-tetrahydro-2-pyrimidinamine, N- (4-hexylphenyl) -l 4,5,6-tetrahydro-2-pyrimidinamine, N- (5-chloro-2-methylphenyl) -2-methoxy-N- (2-oxo-3-oxazolidinyl) -acetamide, N- (6-methoxy) -3-pyridinyl) -cyclopropanecarboxamide, N- [2 , 2,2-trichloro-l - [(chloroacetyl) -amino] -ethyl] -benzamide, N- [3-chloro-4,5-bis- (2-propynyloxy) -phenyl] -N'-methoxy-methanimidoamide , N-formyl-N-hydroxy-DL-alanine, sodium salt O, O-diethyl- [2- (dipropylamino) -2-oxoethyl] -ethyl-phosphoramidothioate, O-methyl-S-phenyl-phenylpropylphosphoramidothioate, S-methyl-1 , 2,3-benzothiadiazole-7-carbothioate, spiro [2 H] -1-benzopyran-2, 1 '(3' H) -isobenzoft? -an-3'-one. Bactericides: Bronopol, Dichlorophen, Nitrapyrin, nickel dimethyldithiocarbamate, Kasugamycin, Octhilinon, furanocarboxylic acid, Oxytetracyclin, Probenazol, Streptomycin, Tecloftalam, copper sulfate and other copper preparations. Insecticides / Acaricides / Nematicides: Abamectin, Acephate, Acetamiprid, Acrinathrin, Alanycarb, Aldicarb, Aldoxycarb, Alpha-cypermethrin, Alphamethrin, Amitraz, Avermectin, AZ 60541, Azadirachtin, Azamethiphos, Azinphos A, Azinphos M, Azocyclotin, Bacillus popilliae, Bacillus sphaericus , Bacillus subtilis, Bacillus thuringiensis, Baculoviren, Beauveria bassiana, Beauveria tenella, Bendiocarb, Benfuracarb, Bensultap, Benzoximate, Betacyfluthrin, Bifenazate, Bifenthrin, Bioethanomethrin, Biopermethrin, BPMC, Bromophos A, Bufencarb, Buprofezin, Butathiophos, Butocarboxim, Butylpiridaben, Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, Chloethocarb, Chlorethoxyphos, Chlorfenapyr, Chlorfenvinphos, Chlorfluazuron, Chlormephos, Chlofyrifos, Chlofyrifos M, Covaporthrin, Cis-Resmethrin, Cispermethrin, Clocythrin, Cloethocarb, Clofentezine, Cyanophos, Cycloprene, Cycloprothrin, Cyfluthrin, Cyhalothrin , Cyhexatin, Cypermethrin, Cyromazine, Deltamethrin, Demeton M, Demeton S, Demeton-S-methyl, Diafenthiuron, Diazinon, Dichlorvos, Diflubenzuron, Dimethoat, Dymethylvinphos, Diofenolan, Disulfoton, Docusat-sodium, Dofenapyn, Eflusilanate, Emamectin, Empenthrin, Endosulfan, Entomopfthora spp., Esfenvalerate, Ethiophencarb, Ethion, Ethoprophos, Etofenprox, Etoxazole, Etrimphos, Fenamiphos, Fenazaquin, Fenbutatin oxide, Fenitrothion, Fenothiocarb, Fenoxacrim, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyrithrin, Fenpyroximate, Fenvalerate, Fipronil, Fluazinam, Fluazuron, Flubrocythrinate, Flucycloxuron, Flucythrinate, Flufenoxuron, Flutenzine, Fluvalinate, Fonophos, Fosmethilan , Fosthiazate, Fubfenprox, Furathiocarb, Granulosevirus, Halofenozide, HCH, Heptenophos, Hexaflumuron, Hexythiazox, Hydroprene, Imidacloprid, Isazophos, Isofenphos, Isoxathion, Ivemectin, Nuclear polyhedrovirus, Lamda-cyhalothrin, Lufenuron, Malathion, Mecarbam, Metaldehyd, Methamidophos, Metarhizium anisopliae , Metharhizium flavoviride, Methidathion, Methiocarb, Methomyl, Methoxyfenozide, Metolcarb, Metoxadiazone, Mevinphos, Milbemectin, Monocrotophos, Naled, Nitenpyram, Nithiazine, Novaluron, Omethoat, Oxamyl, Oxydemethon M, Paecilomyces fumosoroseus, Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalone, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos A, Pirimiphos M, Profenofos, Promecarb, Propoxur, Prothiophos, Prothoat, Pymetrozine, Pyraclofos, Pyresmethrin, Pyrethrum, Pyridaben, Pyridathion, Pyrimidifen, Pyriproxifen, Quinalphos, Ribavirin, Salithion, Sebufos, Silafluofen, Spinosad, Sulfotep, Sulprofos, Tau Fluvalinate, Tebufenozide, Tebufenpyrad, Tebupirimiphos, Teflubenzuron, Tefluthrin, Temephos, Termivinphos, Terbufos, Tetrachlorvinphos, Thetacypermethrin, Thiametohoxam, Thiapronil, Thiatriphos, Thiocyclan hydrogen oxalate, Thiodicarb, Thiofanox, Thuringiensin, Tralocythrin, Tralomethrin, Triarathene, Triazamate, Triazophos, Triazuron, Trichlophenidine, Trichlorfon, Triflumuron, Trimethacarb, Vamidothion, Vaniliprole, Verticillium lecanii, Yl 5302, Zeta-cypermethrin, Zolaprofos, (lR-cis) - [5- (phenylmethyl) -3-furanyl-methyl-3 - [(dihydro-2-oxo-3 (2H) -furanylidene) -methyl] -2,2-dimethylcyclopropanecarboxylate, (3-phenoxyphenyl) -methyl-2,2,3,3-tetramethylcyclopropanecarboxylate, 1 - [(2-chloro-5-thiazolyl) methyl] tetrahydro- 3,5-dimethyl-N-nitro-l, 3,5-lthiazin-2 (lH) -imine, 2- (2-Chloro-6-fluorophenyl) -4- [4- (1, 1-dimethylethyl) phenyl] -4,5-dihydro-oxazole, 2- (acetyloxy) -3-dodecyl-1,4-naphthalenedione , 2-chloro-N- [[[4- (1-phenylethoxy) -phenyl] -amino] -carbonyl] -benzamide, 2-chloro-N - [[[4- (2,2-dichloro-1, -difluoretoxy) -phenyl] -amino] -carbonyl] -benzamide, 3 - . 3-methylphenyl-propylcarbamate, 4- [4- (4-ethoxyphenyl) -4-methylpentyl] -l-fluoro-2-phenoxy-benzene, 4-chloro-2- (1, 1-dimethylethyl) -5 - [[ 2- (2,6-dimethyl-4-phenoxyphenoxy) ethyl] thio] -3 (2H) -pyridazinone, 4-chloro-2- (2-chloro-2-methylpropyl) -5 - [(iodo-3-pyridinyl ) methoxy] -3 (2H) -pyridazinone, 4-chloro-5 - [(6-chloro-3-pyridinyl) methoxy] -2- (3,4-dichlorophenyl) -3 (2H) -pyridazinone, from Bacillus thuringiensis strain EG-2348, [2-benzoyl- l- (l, l-dimethylethyl) -hydrazide of benzoic acid, butanoate of 2,2-dimethyl-3- (2,4-dichlorophenyl) -2-oxo-l-oxaspiro [4.5] dec-3-en-4 -yl, [3 - [(6-chloro-3-pyridinyl) methyl] -2-thiazolidinylidene] -cianamide, dihydro-2- (nitromethylene) -2H-l, 3-thiazine-3 (4H) -carboxaldehyde, ethyl - [2 - [[1,6-dihydro-6-oxo-1- (phenylmethyl) -4-pyridazinyl] oxo] ethyl] -carbamate, N- (3,4,4-trifluor-1-oxo-3) -butenyl) -glycine, N- (4-chlorophenyl) -3- [4- (difluoromethoxy) phenyl] -4,5-dihydro-4-phenyl-lH-pyra2? -l-carboxamide, N - [(2-chloro -5-thiazolyl) methyl] -N'-methyl-N "-nitro-guanidine, N-methyl-N '- (1-methyl-2-propenyl) -1,2-hydrazindicarbotioamide, N-methyl-N" - 2-propenyl-l, 2-hydrazindicarbothioamide, O, O-diethyl- [2- (dipropylamino) -2-oxoethyl] -ethylphosphoramidothioate, It is also possible to mix with other known active ingredients, such as herbicides or even with fertilizers and regulators d growth. The active compounds can be used as such in the form of their formulations or in the forms of application prepared from the above, such as ready-to-use solutions, suspensions, injectable powders, pastes, soluble powders, dusts and granules. The use is carried out in a conventional manner, for example by watering, spraying, sprinkling, spreading, dusting, foaming, brush application, etc. It is also possible to apply the active products also according to the ultra-low volume process or to inject the active product preparation or the active product itself into the soil. The seeds of the plants can also be treated.
When the active compounds according to the invention are used as fungicides, the amounts applied can vary within wide limits, depending on the type of application. When treating parts of plants, the applied amounts of active compound are generally between 0.1 and 10,000 g / ha, preferably between 10 and 1,000 g / ha. In the case of the treatment of the seeds, the quantities of active product are generally between 0.001 and 50 g per kilogram of seeds, preferably between 0.01 and 10 g per kilogram of seeds. When the soil is treated, the application amounts are generally between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g / ha. Examples of obtaining. Example 1.
They are added to a suspension of 0.17 g (4.2 mmoles) of sodium hydride (60% in mineral oil) in 15 ml of tetrahydrofuran, at 0 to 5 ° C, 1.1 g (3.5 mmoles) of 2-methoximino-2 [2- (methylphenoxy) -methylphenyl] -N-methyl-acetamide and the mixture is stirred for 30 minutes additionally. Under additional cooling, 0.483 g (3.9 mmol) of methoxycarbonylsulfenyl chloride are then added dropwise at -70 ° C. The reaction mixture is then stirred overnight at room temperature, the inorganic material is separated by filtration and the solvent is distilled off in a vacuum. The residue is chromatographed with cyclohexane / ethyl acetate (3: 1) on silica gel. 1.24 g (88% of theory) of 2-methoximino-2 [2- (methylphenoxy) -methylphenyl] -N-methyl-N-methoxycarbonylthioacetamide are obtained as a colorless oil. HPLC: logP = 4.25. Example 2 3.15 g (0.00663 mol) of 2- are dissolved. { 2- [6- (2-bromophenoxy) -5-fluoro-pyrimidin-4-yloxy] phenyl} -2-methoxyimino-N-methyl-acetamide in 25 ml of pyridine and refrigerate at 0 ° C. 1.12 g (0.0066 mol) of dichlorofluoromethanesulfenyl chloride are added dropwise and the mixture is subsequently stirred for 8 hours at 5 ° C. The reaction mixture is poured into 200 ml of 2N hydrochloric acid cooled with ice and extracted with diethyl ether. The organic phase is dried over sodium sulfate and the solvent is distilled off in vacuo. The residue is chromatographed with n-hexane: acetone = 4: 1 on silica gel. 0.3 g (6.07% of theory, HPLC content: 81.6%) of 2- are obtained. { 2- [6- (2-bromo-phenoxy) -5-fluoro-pyrimidin-4-yloxy] phenyl} -N- (dichlorofluoro-methylsulfanyl) -2-methoxyimino-N-methylacetamide. logP = 5.10 LC / MS: M = 614, 612, 611,609, 607, 598, 577, 520, 489, 478, 477, 475,459, 457, 388, 366. Spectrum? -NMR (DMSOd6 / TMS): d = 3.35 (3H); 3.74 (3H); 7.29-7.34 (1H); 7.40-7.62 (6H); 7.78-7.81 (1H); 8.17 (1H) ppm. In a manner analogous to that of Examples 1 and 2, and also according to the general description of the process obtained according to the invention for the preparation of the compounds of the formula (I), the compounds of the formula (Ia) were also obtained according to the invention, following, indicated in table I.
Table 1: Example Z G R A logP P.f. (° C) 3 2-ChloroRY -S-CCbF -CH3 -H 5.05 phenyl 4 2-Tolyl -O-CH2- -CN -H -H 3.34 196 2-Tolyl -O-CH 2 -S-CChF -CH 3 -H 5,35 6 2-Tolyl -O-CH 2 -S-CC 13 -CHs -H 5,56 65 7 2-Tolyl -O-CH 2 -4-Fluorophenylthio -CH 3 -H 5,11 8 2-Tolyl -O-CH 2 -CH 3 -H 4,24 9 2-Tolyl -O-CH 2 -SN (C 4 H 9) 2 -CH 3 -H 6,83 10 2-Tolyl -O-CH 2 -CN -CH 3 -H 3.67 11 2-Tolyl -O-CH 2 4-Methoxyphenylthio -CH 3 -H 4,98 12 2-Tolyl -O-CH 2 -COOC 2 H 5 -CH 3 -H 4, 46 Table 1: Table 1: Table 1: Table 1: Table 1: Example Z G R A W logP P.f. (° C) 61 2-Tolyl -O-CH2- -S-CF3 cyclo-H 5,17 propyl 62 2-Tolyl -O-CH 2 -S-CF 3 -C 2 H 5 -H 5,3 63 -. 63 -O-CH2- -S-CChF -CH3 -H 5.69 64 -O-CH 2 -S-CF 3 -CH 3 -H 5,27 65 3-Phenylphenyl -O-CH 2 -S-CChF -CHs -H 5,77 66 3-Phenylphenyl -O-CH 2 -S-CF 3 -CH 3 -H 5,36 67 2,5-Dimethyl- -O-CH 2 -S-CCI 2 F -CHs -H 5,68 phenyl 68 2,5-Dimethyl- -O-CH 2 -S-CF 3 -CH 3 - H 5.25 phenyl 69 2,5-Difluoro- -O-CH 2 -S-CCkF -CH 3 -H 4,86 phenyl 70 2,5-Difluoro- -O-CH 2 -S-CF 3 -CH 3 -H 4 , 48 phenyl Table 1: Ex. RW logP Pf (° C) 71 3-Trifluoro- -S-CH3 -CHs -H 4.73 methylphenyl 72 3-Trifluor-S-Phenyl-CH 3 -H 5,48 methylphenyl 73 3-Trifluoro- -S-C2H5 -CHs -H 5,02 methylphenyl 74 3-Trifluoro-3-trifluoride- -CH 3 -H 5,84 methylphenylphenylphenyl 75 3-Trifluoro- -S-CF3 -CH3 -H 5.36 methylphenyl 6 3-Trifluoro- -CO- -CHs -H 5,22 methylphenyl N (CH 3) -S-CF 3 Table 1: Ex. R W logP P.f. (° C) HS 77 3-Chloro- - -S-CCbF -CH3 -H 5.79 phenyl H3 N- ° 78 3-Chloro- -S-CF3 -CH3 -H 5.39 phenyl 79 3,4-dime- -S-CChF -CH3 -H 4.7 linden 80 3,4-Dime- -S-CF3 -CH3 -H 4,36 toxiphenyl 9H3 81 3-Chlorophenyl? -S- -CH3 -H 4.71 COOCH3 2 3,4-Dimeto- -S- -CH 3 -H 3,7 xyphenyl COOCH 3 Table 1: Example Z G R A W logP P.f. (° C) 83 3-Fluoride-S-CChF-CH3 -H 5.36 phenyl 84 3-Fluorine-S-CF3-CH3 -H 4.97 phenyl 3-Chloro-2-S-CChF-CH3 -H 5.59 128-130 methylphenyl 87 2-Chloro-3-S-CChF-CH 3 -H 4,72 formyl phenyl Table 1: Ex. Z G R A W log P P.f. (° C) 88 Phenyl S-CChF-CHs -H 4.76 89 2-Tolyl-S-CChF-CH3 -H 5.05 90 2,4-Dime-S-CChF-CHs -H 5,41 tilphenyl 91 2,3-Diclo-S-CChF-CHs -H 5,46 Rophenyl 92 2,3-Dime- -S-CChF -CH3 -H 5,34 tilphenyl 93 2-Trifluoro- -S-CChF -CH3 -H 5,2 methoxyphenyl Table 1: Ex. Z R W logP P.f. (° C) 94 2-Difluoro- -S-CChF-CHs -H 4,7 methoxyphenyl- 95 2-Ethylthio- -S-CChF -CH3 -H 5.36 methylphenyl CChF 7 2,6-Dimethyl- S-CChF -CH 3 -H 5,4 phenyl 8 2-Chlorophenyl -S-CChF-CHs -F 4.84 Table 1: Example Z G R A W logP P.f. (° C) trifluoride-toxiphenyl 100 3-Methoxy-S-CChF-CHs -H 5,81 iminomethyl-phenyl 101 3-Bromo-phenyl 102 2,4-Dichloro- -S-CChF -CH3 -H 5.6 phenyl 103 3,5-Dichloro- -S-CChF -CH 3 -H 5,71 phenyl Table 1: Example Z G R A logP P.f. (° C) 104 4-Bromo- • S-CChF-CHs -H 5,19 phenyl 105 2-Fluorophenyl -S-CChF -CH3 -H 4.73 106 3-Trifluoro- -S-CChF -CH3 -H 5,11 methylphenyl 107 4-Cyanophenyl -S-CChF -CHs -H 4.34 108 4-Methoxyphenyl-S-CChF-CH3 -H 4.63 ? P? ox 109 2-Ethylphenyl? -S-CChF -CH 3 -H 5,25 Table 1: , 25 Table 1: Example Z G R A W logP P.f. (° C) 115 3,4-Diclo-S-CChF-CHs -H 5,58 Rophenyl 116 2,4-Difluoro- -S-CChF -CHs -H 4,85 phenyl 117 3-Chlorophenyl -S-CChF -CH3 -H 5.14 118 3-Fluorophenyl -S-CChF-CHs -H 4.76 119 2-Cyanophenyl -S-CChF -CH3 -H 4.28 120 4-Tolyl -S-CChF -CH3 -H 5.02 Table 1: Ex. Z G R A W logP P.f. (° C) 121 2,5-Di- S-CChF-CHs -H 5,34 Methylphenyl 122 2-Allyl-nyl 123 2- (i-pro- -S-CChF -CH3 -H 5.56 pil) phenyl 124 2-Isopro- -S-CChF -CH3 -H 5.88 pil-5-methylphenyl 125 3-Chloro-6-S-CChF-CH 3 -H 5,46 methylphenyl Table 1: Ex. R W logP P.f. (° C) 126 2-Chloro-3 -S-CChF -CH3 -H 5,42 trifluoromethylphenyl 127 4-Yodofeni -S-CChF -CHs -H 5.35 128 3-Tolyl -CChF -CHs -H 4.98 129 2-methoxy- -S-CChF -CH3 -H 4,57 phenyl 130 3-Methoxy-S-CChF-CH 3 -H 4,68 phenyl 131 4-Ethylphenyl -S-CChF-CH3 -H 5.38 Table 1: Ex. R W logP P.f. (° C) 132 3- (t-bu- -S-CChF-CHs -H 5.84 useful) -phenyl 133 4-Trifluor-S-CChF-CHs -H 5,3 methoxyphenyl 134 2- (l-methyl) - S-CChF-CHs -H 5.86 propylphenyl 136 4-Amino-2,3-S-CChF-CHs -H 4,68 dichlorophenyl Table 1: Ex. R W logP P.f. (° C) 137 3-EÜ1-5- -S-CChF -CHs -H 5.76 Methylphenyl 138 2-Methyl-4- -S-CChF-CHs -H 5,65 trifluoromethyl-toxiphenyl 139 4-Trifluor-S-CChF-CHs -H 5,6-methyl-thio-phenyl 140 2-Methoxy-S-CChF-CHs -H 5,03 iminomethylphenyl Table 1: Example Z G R A W logP P.f. (° C) 141 3-Chloro-S-CChF-CHs -H 5.29 128.0 2-methyl-phenyl 142 2-Tetrahi- -O- -S-CChF -CHs -F dropir añilo oil 143 Phenyl-S-CChF-CHs -H 5.48 144 2,6-Difluoro-phenyl -CO-O- -S-CChF -CHs -H 4,41 79 145 -. 145 -CHs -S-CChF -CHs -H 5.45 146 -CHs -O- -S-CChF -CHs -H 3.69 *) The determination of the logP values was carried out according to EEC Directive 79/831 Annex V. A8 by HPLC gradient method, acetonitrile / 0.1% aqueous phosphoric acid).
Application examples: Example A Plasmopara (vine) / protector assay. Solvent: 47 parts by weight of acetone. Emulsifier: 3 parts by weight of alkylaryl polyglycol ether. To obtain a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amounts of solvent and solvent and the concentrate is diluted with water to the desired concentration. To test the protective activity, young plants are sprayed with the preparation of active product at the indicated application amounts. After drying of the spray-applied coating, the plants are inoculated with an aqueous suspension of Plasmopara spores and then remain for 1 day in an incubation chamber at 20 ° C and 100% relative humidity of the air. The plants are then placed for 5 days in the greenhouse at 21 ° C and a relative humidity of approximately 90%. The planas are then moistened and placed in an incubation cabin for one day. The evaluation is carried out 6 days after the inoculation. In this case 0% means a degree of activity that corresponds to that of the untreated controls, while a degree of activity of 100% means that no attack is observed. In this test the compounds indicated in the preparation examples (1), (3), (5), (6), (7), (8), (9), (11), (13), (20) are shown ), (21), (22), (23), (24), (25), (26), (32), (40), (44), (46), (52), (54), (55), (56), (57), (61), (63), (64), (66), (67), (68), (69), (70), (71), (72) ), (73), (75), (86), (88), (91), (92), (93), (97), (100), (101), (102), (105), (106), (109), (117), (128), (141) and (143), with an application amount of 100 g / ha, an activity level of 90% or greater than this value.
Example B Test with Podosphaera (apple tree) / protector Solvent: 47 parts by weight of acetone. Emulsifier: 3 parts by weight of alkylaryl polyglycol ether. To obtain a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amounts of solvent and solvent and the concentrate is diluted with water to the desired concentration. To test the protective activity, young plants are sprayed with the preparation of active compound at the indicated application rates. After drying the spray-applied coating, the plants are inoculated with an aqueous suspension of the anthracnose of the apple tree Podosphaera leucotricha. The plants are then placed in the greenhouse at approximately 23 ° C and with a relative humidity of approximately 70%. The evaluation is carried out 10 days after the inoculation. In this case 0% means a degree of activity that corresponds to that of the untreated controls, while a degree of activity of 100% means that no attack is observed. In this test the compounds indicated in the preparation examples (1), (5), (6), (7), (10), (11), (13), (20), (21), (22) are shown ), (23), (26), (32), (40), (46), (52), (54), (56), (57), (61), (64), (66), (67), (68), (69), (70), (72) ), (75), (86), (88), (91), (92), (100), (101), (141) and (143), with an application quantity of 100 g / ha, a activity level of 90% or greater than this value. EXAMPLE C Assay with Sphaerotheca (cucumber) / protector. Solvent: 47 parts by weight of acetone. Emulsifier: 3 parts by weight of alkylaryl polyglycol ether.
To obtain a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amounts of solvent and solvent and the concentrate is diluted with water to the desired concentration. To test the protective activity, young plants are sprayed with the preparation of active compound at the indicated application rates. After drying the spray applied coating, the plants are inoculated with an aqueous spore suspension of Sphaerotheca fuliginea. The plants are then placed in the greenhouse at approximately 23 ° C and a relative humidity of about 70% in the greenhouse. The evaluation is carried out 10 days after the inoculation. In this case 0% means a degree of activity that corresponds to that of untreated controls, while a degree of activity of 100% means that no attack is observed. In this test, the compounds indicated in the preparation examples (1), (3), (5), (6), (7), (8), (9), (11), (12), (13) are shown ), (20), (21), (22), (23), (24), (25), (26), (32), (40), (44), (45), (46), (52), (54), (55), (56), (57), (61), (63), (64), (66), (67), (68), (69), (71) ), (72), (73), (75), (86), (88), (91), (92), (93), (97), (100), (101), (102), (105), (106), (109), (117), (128), (141) and (143), with an application amount of 100 g / ha, an activity level of 90% or greater than this value. Example D Test with Venturia (apple tree) / protector. Solvent: 47 parts by weight of acetone. Emulsifier: 3 parts by weight of alkylaryl polyglycol ether. To obtain a suitable active product preparation, 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration. To test the protective activity, young plants are sprayed with the preparation of active compound at the indicated application rates. After drying of the spray-formed coating, the plants are inoculated with an aqueous suspension of conidia of the anthracnose pathogen Venturia inaequalis and then remain for 1 day at 20 ° C and 100% relative humidity in an incubation chamber. The plants are then placed in the greenhouse at approximately 21 ° C and with a relative humidity of approximately 90%. The evaluation is carried out 12 days after the inoculation. In this case 0% means a degree of activity that corresponds to that of untreated controls, while a degree of activity of 100% means that no attack is observed. In this test the compounds indicated in the preparation examples (1), (3), (5), (6), (7), (8), (9), (10), (11), (12) are shown ), (13), (14), (15), (20), (21), (22), (23), (24), (25), (26), (32), (40), (44), (52), (54), (55), (56), (57), (63), (64), (66), (71), (72), (73), (75 ), (86), (88), (91), (92), (93), (97), (100), (101), (102), (105), (106), (109), (117), (128), (141) and (143), with an application amount of 10 g / ha, an activity level of 90% or greater than this value. Example E: Test with Pyricularia (rice) / protector Solvent: 25 parts by weight of N, N-dimethylacetamide Emulsifier: 0.6 parts by weight of alkylaryl polyglycol ether To obtain a suitable preparation of active compound, 1 part by weight of the active product with the indicated amount of solvent and the concentrate is diluted with water and with the indicated amount of emulsifier to the desired concentration. To test the protective activity, young rice plants are sprayed with the preparation of the active compound in the indicated application amount. After drying the spray applied coating, the plants are inoculated with an aqueous spore suspension of Pyricularia oryzae. The plants are then placed in a greenhouse at a temperature of 25 ° C and a relative humidity of 100%. The evaluation is carried out 4 days after the inoculation. In this case 0% means a degree of activity, which corresponds to that of the controls, while a degree of activity of 100% means that no attack is observed. In this test the products according to the invention, indicated in examples (1) and (5), with an application amount of 125 g / ha, an activity level of 90% or above this value, are shown. Example F Test with Erysiphe (barley) / protector. Solvent: 25 parts by weight of N, N-dimethylacetamide. Emulsifier: 0.6 parts by weight of alkylaryl polyglycol ether. To obtain a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration. To test the protective activity, young plants are sprayed with the preparation of the active compound in the indicated application amounts. After drying of the spray-applied coating the plants are sprinkled with spores of Erysiphe graminis f.sp. hordei The plants are placed in a greenhouse at a temperature of about 20 ° C and a relative humidity of about 80% to promote the development of powdery mildew pustules. The evaluation occurs 7 days after the inoculation. In this case 0% means a degree of activity, which corresponds to that of the controls, while a degree of activity of 100% means that no attack is observed. In this test it shows the product according to the invention, indicated in example (5), with an application amount of 250 g / ha, an activity degree of 90% or above this value. Example G Test with Erysiphe (wheat) / protector. Solvent: 25 parts by weight of N, N-dimethylacetamide. Emulsifier: 0.6 parts by weight of alkylaryl polyglycol ether. To obtain a suitable preparation of active ingredients, 1 part by weight of the active compound is mixed with the indicated amounts of solvent and emulsifier and diluted with water to the desired concentration. To check the protective activity, young plants are sprayed with the preparation of active product in the indicated application quantities. After drying the spray-applied coating, the plants are sprinkled with spores of Erysiphe graminis f. sp. tritici. The plants are placed in a greenhouse at a temperature of about 20 ° C and a relative humidity of about 80% to promote the development of powdery mildew pustules. The evaluation occurs 7 days after the inoculation. In this case 0% means a degree of activity, which corresponds to that of the controls, while a degree of activity of 100% means that no attack is observed.
In this test it shows the product according to the invention, indicated in example (5), with an application amount of 250 g / ha, an activity degree of 90% or above this value. Example H Pucinia (wheat) / protector test Solvent: 25 parts by weight of N, N-dimethylacetamide Emulsifier: 0.6 parts by weight of alkylaryl polyglycol ether. To obtain a suitable preparation of active compound, 1 part by weight of the active compound is mixed with the indicated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration. To test the protective activity, young plants are inoculated with the preparation of active compound in the indicated application amounts. After drying of the spray-applied coating, the plants are sprayed with a conidial suspension of recondite Puccinia. The plants remain for 48 hours at 20 ° C and with a relative humidity of 100% in an incubation cabinet. The plants are then placed in a greenhouse at a temperature of about 20 ° C and with a relative humidity of about 80%, to favor the development of rust pustules. The evaluation is carried out 10 days after the inoculation. In this case 0% means a degree of activity, which corresponds to that of the controls, while a degree of activity of 100% means that no attack is observed. In this test it shows the product according to the invention, indicated in example (5), with an application amount of 250 g / ha, an activity degree of 90% or above this value.
EXAMPLE I Assay with Fusarium nivale (var. Nivale) (wheat) / protector. Solvent: 25 parts by weight of N, N-dimethylacetamide. Emulsifier: 0.6 parts by weight of alkylaryl polyglycol ether. To obtain a suitable active product preparation, 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration. To test the protective activity, young plants are sprayed with the preparation of active compound at the indicated application rates. After drying the spray-applied coating, the plants are sprinkled with a suspension of conids of Fusarium nivale (var. Nivale). The plants are placed in a greenhouse, under incubation caps transparent to light, at a temperature of approximately 15 ° C and a relative humidity of approximately 100%. The evaluation is carried out 4 days after the inoculation. In this case 0% means a degree of activity that corresponds to that of the untreated controls, while a degree of activity of 100% means that no attack is observed. In this test, the compounds indicated in the preparation examples (5), (67), (68), (100), (101), (102), (103), (104), (105), (106) are shown ), (109), (114), (115), (116), (117), (118), (119), (120), (121), (122), (123), (124), (125), (126), (130), (134), (138) and (139), with an application amount of 250 g / ha, an activity level of 90% or greater than this value.
E emplo K Test with Erysiphe (barley) / healing. Solvent: 25 parts by weight of N, N-dimethylacetamide. Emulsifier: 0.6 parts by weight of alkylaryl polyglycol ether. To obtain a suitable active product preparation, 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration. To test the curative activity, young plants are sprayed with spores of Erysiphe graminis f.sp. hordei After 48 hours from the inoculation, the plants are sprayed with the preparation of active compound at the indicated application rates. The plants are placed in a greenhouse at a temperature of approximately 20 ° C and a relative humidity of approximately 80%, to favor the development of the powdery mildew pustules. The evaluation is carried out 7 days after the inoculation. In this case 0% means a degree of activity that corresponds to that of the untreated controls, while a degree of activity of 100% means that no attack is observed. In this test, the compounds indicated in the preparation examples (5), (67), (68), (100), (101), (102), (103), (106), (107), (108) are shown ), (109), (110), (113), (114), (115), (116), (117), (119), (123), (124), and (128), with an application amount of 250 g / has, an activity level of 90% or greater than this value. It is noted that in relation to this date, the best method known to the applicant, to carry out the aforementioned invention is that which is clear from the present description of the invention.

Claims (2)

CLAIMS Having described the invention as above, property is claimed as contained in the following claims: 1.- Compounds of the formula (I), characterized in that A means hydrogen, alkoxycarbonyl, methyl, ethyl or cyclopropyl, or has the same meaning as R, R means alkylthio, haloalkylthio, arylthio, optionally substituted, alkoxycarbonylthio, alkylthiocarbonyl, -SY, -SN (R! R2), -CO-N (R3R4), -CN, -CH2-O-R5, -PO (OR6) R7, -PS (OR6) R7, wherein R1 means alkyl, R2 means alkyl, alkoxycarbonyl, or together with R1 as well as with the nitrogen atom, to which they are linked, means a substituted heterocyclic ring, R3 signifies alkyl or optionally substituted aryl, R4 signifies alkylthio, alkylsulfonyl or haloalkylthio or together with R3, as well as with the nitrogen atom, with which they are linked, means a substituted heterocyclic ring if appropriate, R5 means alkyl, R6 signifies alkyl, R7 signifies alkyl, alkoxy or alkylamino, Y signifies the same grouping that is already linked to the S- atom, or, when A means methyl, R sign also means alkylcarbonyl, alkoxycarbonyl, halogenoalkoxycarbonyl, alkoxycarbonylcarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylsulfonyl or substituted arylsulfonyl, if appropriate, G means a single bond, means oxygen, sulfur or means alkanediyl, alkenodiyl, alkynediyl substituted, if appropriate by halogen, by hydroxy, by alkyl, by haloalkyl or by cycloalkyl, means one of the following groups, in which the left side is linked respectively with Z: -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-, -CH2-S (O) n-, -CQ-, -S (O) n -CH2-, -C (R8) -N (R9) -, -CQ-N (R9) -, -N (R9) -CQ-, -Q-CQ-N (R9) -, -CH (R8) -ON = CH-, -C (R8) = NN = CH-, -N (R9) -CQ-Q-, -CQ -N (R9) -CQ-Q-, -N (R9) -CQ-Q-CH2-, -O-CH2-C (R8) = NO-CH2-, -N = NC (R8) = NO-CH2 -, -C (= NO-R10) -C (R8) = NO-CH2-, -C (= NO-R10) -C (R8) -ON = CH-, -C (= NO-R10) -C (R8) = NN = CH-, -C (= NO-R10) -C (R8) -ON = C (CHs) -, -T-Ar1- or T-Ar'-Q-, where Ar1 means arylene, optionally substituted heteroarylene, cycloalkylene or heterocycloalkylene (ie a double-linked aliphatic ring, in which one or more carbon atoms are replaced by heteroatoms, ie by atoms that are different from carbon), n means the numbers 0, 1 or 2, Q oxygen or sulfur, R8 means hydrogen, cyano, or means alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or cycloalkyl respectively substituted, R9 means hydrogen, hydroxy, cyano or means optionally substituted alkyl, alkoxy or cycloalkyl, R10 signifies hydrogen, alkyl or substituted benzyl if appropriate and T means a single bond, means oxygen, sulfur, -CH2-O-, -CH2-S- or means alkanediyl substituted, if appropriate, L ', L2, L3 and L4 are the same or different and independently of each other denote hydrogen, halogen or alkyl, W denotes hydrogen, fluorine, cyano or thiocyanate and Z means alkyl, alkenyl, alkynyl, optionally substituted cycloalkyl, aryl or heterocyclyl, respectively. 2. Compounds according to claim 1, characterized patchy = A means hydrogen, methyl, ethoxycarbonyl, ethyl or cyclopropyl or has the same meaning as R, R means alkylthio, haloalkylthio, alkoxycarbonylthio, alkylthiocarbonyl, with 1 to 4 carbon atoms in each the alkyl, phenylthio chain optionally substituted by halogen, by cyano, by alkyl, by alkoxy or by alkoxycarbonyl with 1 to 4 carbon atoms, by haloalkyl or by haloalkoxy with 1 to 4 carbon atoms and 1 to 9 carbon atoms of halogen equal or different, -SY-, -SN (R'R2), -CO-N (R3R4), -CN, -CH2-O-R5, -PO (OR6) R7, -PS (OR6) R7. R1 means alkyl with 1 to 4 carbon atoms, R2 means alkyl with 1 to 4 carbon atoms, alkoxycarbonyl with 1 to 4 carbon atoms in the alkyl part, or together with R 1, as well as with the nitrogen atom, with which they are bound, means a heterocyclic ring with 5 or 6 members in the ring, optionally substituted by methyl or ethyl , R3 denotes alkyl having 1 to 4 carbon atoms or phenyl optionally substituted by halogen, alkyl or alkoxy respectively 1 to 6 carbon atoms, for halogenalkyl or for halogenalkoxy with 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, R4 means alkylthio or alkylsulfonyl with 1 to 4 carbon atoms or halogenalkylthio with 1 to 4 carbon atoms carbon atoms and 1 to 5 identical or different halogen atoms or together with R3, as well as with the nitrogen atom, to which they are bonded, means a heterocyclic ring with 5 or 6 ring members, optionally substituted by methyl or ethyl, R5 means alkyl with 1 to 4 carbon atoms, R6 means alkyl with 1 to 4 carbon atoms, R7 means alkyl, alkoxy or alkylamino with 1 to 4 carbon atoms in the alkyl chains, Y means the same grouping which is already bonded to the sulfur atom, or, when A means methyl, also means alkylcarbonyl, alkoxycarbonyl, alkoxycarbonylcarbonyl, halogenoalkoxycarbonyl, alkylaminocar bonyl, dialkylaminocarbonyl, alkylsulfonyl with 1 to 4 carbon atoms in the alkyl or phenylsulfonyl chains, optionally substituted by alkyl with 1 to 4 carbon atoms, means a single bond, means oxygen, sulfur or means alkanediyl, alkenodiyl, alkynediyl, with respectively up to 4 carbon atoms, respectively substituted, if appropriate, by halogen, by hydroxy, by alkyl with 1 to 4 carbon atoms, by halogenalkyl with 1 to 4 carbon atoms or by cycloalkyl with 3 to 6 carbon atoms means one of the following groupings, in which the left side is linked respectively with Z: -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 (R8) = NO-, -C (R8) = NO-CH2-, -N (R9) ) -, -CQ-N (R9) -, -N (R9) -CQ-, -Q-CQ-N (R9) -, -N = C (R8) -Q-CH2-, -CH (R8) -ON = CH-, -C (R8) = NN = CH-, -N (R9) -CQ-Q-, -CQ-N (R9) -CQ-Q-, -N (R9) -CQ-Q -CH2-, - QC (R8) = NO-CH2-, -N (R9) -C (R8) = NO-CH2-, -O-CH2-C (R8) = NO-CH2-, -N = NC (R8) = NO-CH2-, -C (= NOR, 0) -C (R8) = NO-CH2-, -C (= NO-R10) -C (R8) -ON = CH-, -C ( = NO-R10) -C (R8) = NN = CH-, -C (= NO-R10) -C (R8) -ON = C (CHs) -, -T-Ar1- or T-Ar'-Q -, where n means the numbers 0, 1 or 2, Q signifies oxygen or sulfur, R8 signifies hydrogen, cyano, means alkyl, alkoxy, alkylthio, alkylamino or dialkylamino with respectively 1 to 6 carbon atoms in the alkyl groups, respectively substituted optionally by halogen, by cyano or by alkoxy with 1 to 4 carbon atoms, or by cycloalkyl having 3 to 6 carbon atoms substituted, if appropriate, by halogen, by by carboxy, by alkyl with 1 to 4 carbon atoms or by alkoxycarbonyl with 1 to 4 carbon atoms, and R9 means hydrogen, hydroxy, cyano, or means alkyl having 1 to 6 carbon atoms, optionally substituted by halogen , by cyano or by alkoxy with 1 to 4 carbon atoms, or means cycloalkyl with 3 to 6 carbon atoms, optionally substituted by halogen, cyano, carboxy, alkyl with 1 to 4 carbon atoms or by alkoxy carbonyl with 1 to 4 carbon atoms, R10 denotes hydrogen, alkyl having 1 to 4 carbon atoms or benzyl optionally substituted by halogen, by alkyl or by alkoxy with 1 to 6 carbon atoms, by haloalkyl or by haloalkoxy with respectively 1 to 6 carbon atoms and 1 to 13 same or different halogen atoms, T means a single bond, means oxygen, sulfur, -CH2-O-, -CH2-S- or means alkanediyl with 1 to 3 carbon atoms , Ar1 means phenylene, naphthylene, cycloalkylene respectively substituted one or more times, in the same or different forms, or heteroarylenes or heterocycloalkylenes with 3 to 7 members in the ring, one of which being at least oxygen, sulfur or nitrogen and if desired one or two more nitrogen, the possible substituents being preferably chosen from the following enumeration: halogen, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl; alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulphonyl respectively straight-chain or branched chain, with respectively 1 to 6 carbon atoms, alkenyl or alkenyloxy respectively straight-chain or branched chain with respectively 2 to 6 carbon atoms; respectively straight-chain or branched halogenalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulfinyl or halogenoalkylsulfonyl having respectively 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms; halogenoalkenyl or halogenoalkenyloxy respectively straight-chain or branched chain with respectively 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms; alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydroximinoalkyl or alkoximinoalkyl, respectively straight-chain or branched chain, each having 1 to 6 carbon atoms in the individual alkyl portions, as well as; cycloalkyl with 3 to 6 carbon atoms. L1, L2, L3 and L4 are the same or different and independently of one another denote hydrogen, fluorine, chlorine, bromine, methyl, ethyl, or n- or i-propyl, n-, i-, s- or t-butyl , W means hydrogen, fluorine, cyano or thiocyanate and means alkyl with 1 to 8 carbon atoms, optionally substituted one or more times, in the same or different ways by halogen, cyano, hydroxy, amino, alkoxy with 1 to 4 carbon atoms, for alkylthio having 1 to 4 carbon atoms, for alkylsulfinyl with 1 to 4 carbon atoms or for alkylsulfonyl with 1 to 4 carbon atoms (which may be substituted, if appropriate, by halogen); means alkenyl or alkynyl with respectively up to 8 carbon atoms, each optionally substituted by halogen; tetrahydropyranyl; means cycloalkyl with 3 to 6 carbon atoms, each optionally substituted one or more times, in the same or different manner by halogen, by cyano, by carboxy, by phenyl (which is optionally substituted by halogen, by cyano, by alkyl with 1 to 4 carbon atoms, by halogenalkyl with 1 to 4 carbon atoms, by alkoxy with 1 to 4 carbon atoms or by halogenalkoxy with 1 to 4 carbon atoms), by alkyl with 1 to 4 carbon atoms or by alkoxycarbonyl having 1 to 4 carbon atoms; means phenyl, naphthyl, tetrahydrobenzofuran respectively substituted one or more times, in the same or different forms or means heterocyclyl with 3 to 7 members in the ring, one of which being at least oxygen, sulfur or nitrogen and in case given one or two more are nitrogen, the possible substituents being preferably chosen from the following enumeration: halogen, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl; formyl; alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl respectively straight-chain or branched chain with 1 to 6 carbon atoms respectively; substituted t-butyl tetrazole; alkenyl or alkenyloxy respectively straight-chain or branched chain with respectively 2 to 6 carbon atoms; respectively straight-chain or branched halogenalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulfinyl or halogenoalkylsulfonyl having respectively 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms; phenyl; halogenoalkenyl or halogenoalkenyloxy respectively straight-chain or branched chain with respectively 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms; alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl Or straight-chain or branched chain alkylsulfonyloxy, respectively having 1 to 6 carbon atoms in the individual alkyl portions; alkylene or dioxyalkylene having respectively 1 to 6 carbon atoms, respectively doubly linked, each optionally substituted one or more times, in the same or different manner by halogen and / or straight-chain or branched-chain alkyl with 1 to 4 carbon atoms and / or by straight-chain or branched-chain halogenoalkyl with 1 to 4 carbon atoms and 1 to 9 same or different halogen atoms; cycloalkyl with 3 to 6 carbon atoms; heterocyclyl or heterocyclylmethyl with respectively 3 to 7 members in the ring, 1 to 3 of which, respectively, are the same or different heteroatoms -especially nitrogen, oxygen and / or sulfur-, or a group A1- > \ _ J * N wherein A1 means alkyl having 1 to 4 carbon atoms or cycloalkyl with 1 to 6 carbon atoms and A2 means alkyl having 1 to 4 carbon atoms, alkenyl or alkynyl with 2 to 4 carbon atoms, optionally substituted by cyano , by alkoxy, by alkylthio, by alkylamino, by dialkylamino or by phenyl. 3. Compounds of the formula (I), characterized in that A means hydrogen, methyl, ethoxycarbonyl, ethyl or cyclopropyl, or has the same meaning as R, R means methylthio, ethylthio, n- or i-propylthio, n-, i -, s- or t-butylthio, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, dichlorofluoromethylthio, tichloromethylthio, 2,2,2-trifluoroethylthio, 1,1-difluoroethylthio, methoxycarbonylthio, ethoxycarbonylthio, methylthiocarbonyl, ethylthiocarbonyl, n- or i-propylthiocarbonyl, substituted phenylthio optionally one to three times, fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propylthio, n-, i-, s- or t-butyl, methoxy, by ethoxy, by n- or i-propoxy, by trifluoromethyl, by trifluoroethyl, by difluoromethoxy, by trifluoromethoxy, by difluorochloromethoxy, by trifluoroethoxy, by methoxycarbonyl or by ethoxycarbonyl, -SY, -SN (R'R2), -CO -N (R3R4), -CN, -CH2-O-R5, -PO (OR6) R7, -PS (OR6) R7, where R1 signifies methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, R2 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxycarbonyl or ethoxycarbonyl, or together with R1 as well as with the nitrogen atom, with which are linked, means pyrrolidino, piperidino, or morpholino, optionally substituted by methyl or ethyl, R3 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or substituted phenyl optionally one to three times fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy , by ethoxy, by n- or i-propoxy, by trifluoromethyl, by trifluoroethyl, by difluoromethoxy, by trifluoromethoxy, by difluorochloromethoxy, by trifluoroethoxy, by methoxycarbonyl or by ethoxycarbonyl, R4 means methylthio, ethylthio, n- or i-propylthio, n -, i-, s- or t-butylthio, methylsulfonyl, ethylsulphonyl, n- or i-propylsulphonyl, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, dichlorofluoromethylthio, trichloromethylthio or 2,2,2-trifluoroethylthio, or together with R3, as well as with the nitrogen atom, with which they are bound, means pyrrolidino, piperidino or morpholino, optionally substituted by methyl or ethyl, R5 means methyl, ethyl, n- or i-propyl, n- , i-, s- or t-butyl, R6 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, R7 signifies methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylamino, ethylamino, dimethylamino or diethylamino, Y means the same crush which is already bound to the sulfur atom, or, when A means methyl, R also means acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, i-butoxycarbonyl, methoxycarbonylcarbonyl, 2-bromoethoxycarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methylsulfonyl, ethylsulfonyl, phenylsulfonyl or tolylsulfonyl, G stands for oxygen or means dimethylene (ethane-1,2- diyl), ethene-1, 2-diyl, respectively substituted, if appropriate, by fluorine, by chlorine or by bromine or means one of the following groupings, in which the left side is linked respectively with Z: -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-, -CH2-S (O) n-, -CQ-, -S (O) n -CH2-, -C (R8) = NO-, -C (R8) = NO-CH2-, -N (R9) - , -CQ-N (R9) -, -N (R9) -CQ-, -Q-CQ-N (R9) -, -N = C (R8) -Q-CH2-, -CH (R8) -ON = CH-, -C (R8) = NN = CH-, -N (R9) -CQ-Q-, -CQ-N (R9) -CQ-Q-, -N (R9) -CQ-Q-CH2-, - QC (R8) = NO- CH2-, -N (R9) -C (R8) -N = NC (R8) = NO-CH2-, -C (= NO-R10) -C (R8) = NO-CH2-, -C (= NO -R10) -C (R8) -ON = CH-, -C (= NO-R10) -C (R8) = NN = CH-, -C (= NOR, 0) -C (R8) -ON = C (CHs) -, -T-Ar1- or T-Ar'-Q-, where n means the numbers 0, 1 or 2, Q means oxygen or sulfur, R8 means hydrogen, cyano, methyl, ethyl or cyclopropyl and R9 means hydrogen, methyl, ethyl or cyclopropyl, R10 means hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or means benzyl optionally substituted by fluorine, by chlorine, by bromine , by cyano, by methyl, by ethyl, by n- or i-propyl, by n-, i-, s- or t-butyl, by methoxy, by ethoxy, by non-propoxy, by trifluoromethyl, by trifluoroethyl, by difluoromethoxy, by trifluoromethoxy, by difluorochloromethoxy or by trifluoroethoxy, T means a single bond, means oxygen, sulfur re, -CH2-O-, -CH2-S- or means substituted alkanediyl, if appropriate, Ar1 means phenylene or pyridinediyl substituted, if appropriate, one to three times, in the same or different forms, means pyrimidindiyl, pyridazindiyl, pyrazindiyl, 1,2,3-triazindiyl, 1,2,4-triazindiyl or 1,3,5-triazindiyl respectively monosubstituted, if appropriate, or means 1,4-thiadiazoldiyl, 1,3,4-thiadiazoldyl,
1,2,4-oxadiazoldiyl, 1,3,4-oxadiazoldiyl, the possible substituents being preferably chosen from the following enumeration: fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, cyclopropyl, methoxy, ethoxy , n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, metiisulfonilo or etiisulfonilo, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, diflúorclorometoxi, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl and L1 , L, L3 and L4 are the same or different and respectively independently of each other, hydrogen, fluorine, chlorine, bromine, methyl or ethyl, W means hydrogen, fluorine, cyano or thiocyanate, and means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, allyl, 2-buten-l-yl, 2- (l-methyl) -propyl, 2-methyl-2-buten-l-yl, propargyl , tetrahydropyranyl, tetrazol t-butyl substituted or means phenyl, 1,2,4-thiadiazolyl, 1,3,4- thiadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, pyridinyl, pyrimidyl, tetrahydrobenzofuranyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl or 1,3,5- triazinyl substituted, if appropriate, one to three times, in the same or in different ways, the possible substituents being preferably chosen from the following enumeration: amino, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, formyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, non-propylthio, methylisulfinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl, methoxycarbonyl, ethoxycarbonyl, phenyl, means methylenedioxy, ethylenedioxy, respectively doubly linked, respectively substituted one to four times or sometimes, in the same or different ways by fluorine, chlorine, methyl, trifluoromethyl or ethyl, or means a grouping YEAR where A means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl, or cyclobutyl and A2 means methyl, ethyl, n- or i-propyl, n-, i- , s- or t-butyl, allyl, propargyl, but-2-en-l-yl, 2-methyl-prop-l-en-3-yl, cyanomethyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, methylthioethyl, ethylthioethyl, dimethylaminomethyl, dimethylaminoethyl, methylaminomethyl, methylaminoethyl or benzyl. 4. Compounds of the formula (I) according to claim 1, characterized by park A means hydrogen, ethoxycarbonyl, methyl or ethyl, cyclopropyl, or has the same meaning as R, R means methylthio, ethylthio, n- or i-propylthio , n-, i-, s- or t-butylthio, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, dichlorofluoromethylthio, trichloromethylthio, 2,2, 2-trifluoroethylthio, 1,1-difluoroethylthio, methoxycarbonylthio, ethoxycarbonylthio, methylthiocarbonyl, ethylthiocarbonyl, n- or i-propylthiocarbonyl, phenylthio substituted one to three times, fluorine, chlorine, bromine, by cyano, by methyl, by ethyl, by n- or i-propyl, by n-, i-, s- or t-butyl, by methoxy, by ethoxy, by n- or i-propoxy, by trifluoromethyl, by trifluoroethyl , by difluoromethoxy, by trifluoromethoxy, by difluorochloromethoxy, by trifluoroethoxy, by methoxycarbonyl or by ethoxycarbonyl, -SY, -SN (R) R2), -CO-N (R3R4), -CN, -CH2-O-R5, -PO (OR6) R7, -PS (OR6) R7, where R1 signifies methyl, ethyl, n- or i-propyl, n-, i-, - s- or t-butyl, R2 means methyl, ethyl, n- or i -propyl, n-, i-, s- or t-butyl, methoxycarbonyl or ethoxycarbonyl, or together with R 1, as well as with a nitrogen atom, with which they are bound, mean pyrrolidino, piperidino or morpholino, optionally substituted by methyl or ethyl, R3 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or phenyl optionally substituted one to three times, fluorine, chlorine, bromine, cyano, nitro, methyl, n- or i-propyl, by n-, i-, s- or t-butyl, by methoxy, by ethoxy, by n- or i-propoxy, by trifluoromethyl, by trifluoroethyl, by difluoromethoxy, by trifluoromethoxy, by difluorochloromethoxy, by trifluoroethoxy , by methoxycarbonyl or by ethoxycarbonyl, R4 means methylthio, ethylthio, n- or i-propylthio, n- i-, s- or t-butylthio, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, dichlorofluoromethylthio , trichloromethylthio or 2,2,2-trifluoroethylthio, or together with R3 as well as with the nitrogen atom, to which they are bound, mean pyrrolidino, piperidino or morpholino, optionally substituted by methyl or ethyl, R5 means methyl, ethyl , n- or i-propyl, n-, i-, s- or t-butyl, R6 means methyl, ethyl, n- or i-propyl, n-, i, -s- or t-butyl, R7 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylamino, ethylamino, dimethylamino or diethylamino, Y means the same grouping as is bonded to the sulfur atom, or, when A means methyl, also means acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, i-butoxycarbonyl, methoxycarbonylcarbonyl, 2-bromoethoxycarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methylsulfonyl, ethylsulfonyl, phenylsulfonyl or tolylsulfonyl, G stands for oxygen or especially -O-CH2-, L1, L2, L3 and L4 mean hydrogen, W means hydrogen, fluorine, cyano or thiocyanate, and Z means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, allyl, 2-buten-1-yl, 2-methyl-2-buten-1-yl, propargyl, tetrahydropyranyl or phenyl means respectively substituted one to three times, in the same or in the same way different, the possible substituents being chosen preferably from the following enumeration: fluorine, chlorine or, 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, metiisulfonilo or etiisulfonilo, trifluoromethyl, diflúormetoxi.triflúormetoxi, diflúorclorometoxi, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl, methoxycarbonyl, ethoxycarbonyl, phenyl, methylenedioxy or ethylenedioxy respectively doubly attached respectively substituted optionally a four times, in the same or different ways by fluorine, chlorine, methyl, trifluoromethyl or ethyl or a group A ^ N wherein A1 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl or cyclobutyl and A2 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, allyl, propargyl, but-2-en-l-yl, 2-methyl-prop-l-en-3-yl, cyanomethyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, methylthioethyl , ethylthioethyl, dimethylaminomethyl, dimethylaminoethyl, methylaminomethyl, methylaminoethyl or benzyl. 5. Compounds of the formula (I) according to claim 1, characterized by perc. A means hydrogen, ethyl or methyl, or has the same meaning as R, R means methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, dichlorofluoromethylthio, trichloromethylthio, 2,2,2-trifluoroethylthio, methoxycarbonylthio, ethoxycarbonylthio, methylthiocarbonyl, ethylthiocarbonyl, n- or i-propylthiocarbonyl, phenylthio substituted, optionally, one to three times, fluorine, chlorine, bromine, cyano, methyl , by ethyl, by n- or i-propyl, by n-, i-, s- or t-butyl, by methoxy, by ethoxy, by n- or i-propoxy, by trifluoromethyl, by trifluoroethyl, by difluoromethoxy, by trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, methoxycarbonyl or ethoxycarbonyl, -SY, -SN (R'R2), -CO-N (R3R4), -CN, -CH2-O-R5, -PO (OR6) R7, -PS (OR6) R7, where R1 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, R2 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxycarbonyl or ethoxycarbon nyl, or together with R 1, as well as with the nitrogen atom, with which they are linked, means pyrrolidino, piperidino or morpholino, optionally substituted by methyl or ethyl, R 3 signifying methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, phenyl optionally substituted one to three times by fluorine, by chlorine, by bromine, by cyano, by methyl, by ethyl, by n- or i-propyl, by n-, i-, s- or t-butyl, by methoxy, by ethoxy, by n- or i-propoxy, by trifluoromethyl, by trifluoroethyl, by difluoromethoxy, by trifluoromethoxy, by difluorochloromethoxy, by trifluoroethoxy, by methoxycarbonyl or by ethoxycarbonyl R 4 means methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, dichlorofluoromethylthio, trichloromethylthio, or , 2,2-trifluoroethylthio, or together with R 3, as well as with the nitrogen atom, with which they are bound, means pyrrolidino, p iperidino or morpholino, optionally substituted by methyl or ethyl, R5 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, R6 means methyl, ethyl, n- or i- propyl, n-, i, -s- or t-butyl, R7 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i- propoxy, methylamino, ethylamino, dimethylamino or diethylamino, Y means the same group which is already bonded to the sulfur atom, or, when A means methyl, R also means acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methoxycarbonylcarbonyl, 2-bromoethoxycarbonyl, methylaminocarbonyl , dimethylaminocarbonyl, methylsulfonyl, ethylsulfonyl, phenylsulfonyl or tolylsulfonyl. G means -C (R8) = NO-CH2, R8 means cyclopropyl or especially methyl, L1 ', TV2, TV3 and V mean hydrogen, W means hydrogen, fluorine, cyano or thiocyanate and Z means methyl, ethyl, n - or i-propyl, n-, i-, s- or t-butyl, allyl, 2-buten-1-yl, 2-methyl-2-buten-1-yl, propargyl, or means pyridyl, pyrimidyl, or , especially phenyl, each optionally substituted one to three times, in the same or in different ways, the possible substituents being preferably chosen as the following number: 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, methylisulfinyl, ethylsulfyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy , difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethyl-sulphonyl or trifluoromethyl-sulfonyl, methoxycarbonyl, ethoxic respectively double-bonded arbonyl, methoximinomethyl, ethoxyminomethyl, methoxymethyl, ethoxymethyl, methylenedioxy or ethylenedioxy, each optionally substituted one to four times, in the same or different ways by fluorine, chlorine, methyl, trifluoromethyl or ethyl. 6. Compounds of the formula (I) according to claim 1, face? eriza ± e pceque A means hydrogen, ethyl or methyl, or has the same meaning as R, R means methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, difluoromethylthio , trifluoromethylthio, difluorochloromethylthio, dichlorofluoromethylthio, trichloromethylthio, 2,2,2-trifluoroethylthio, methoxycarbonylthio, ethoxycarbonylthio, methylthiocarbonyl, ethylthiocarbonyl, n- or i-propylthiocarbonyl, phenylthio substituted one to three times, fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, trifluoromethyl, by trifluoroethyl, by difluoromethoxy, by trifluoromethoxy, by difluorochloromethoxy, by trifluoroethoxy, by methoxycarbonyl or by ethoxycarbonyl, -SY, -SN (R'R2), -CO-N (R3R4), -CN, -CH2-O-R5, -POÍOR ^ R7, -PS (OR6) R7, where R1 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, R2 means methyl, ethyl, n- or i- propyl, n-, i-, s- or t-butyl, methoxy arbonyl or ethoxycarbonyl, or together with R 1, as well as with the nitrogen atom, with which they are bound, means pyrrolidino, piperidino or morpholino, optionally substituted by methyl or ethyl, R 3 means methyl, ethyl, n- or i- propyl, n-, i-, s- or t-butyl or phenyl, optionally substituted one to three times, fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i- propyl, by n-, i-, s- or t-butyl, by methoxy, by ethoxy, by n- or i-propoxy, by trifluoromethyl, by trifluoroethyl, by difluoromethoxy, by trifluoromethoxy, by difluorochloromethoxy, by trifluoroethoxy, by methoxycarbonyl or by ethoxycarbonyl, R4 means methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, dichlorofluoromethylthio, trichloromethylthio or 2,2,2-trifluoroethylthio, or together with R 3, as well as with the nitrogen atom, with which they are linked, Examples of pyrrolidino, piperidino or morpholino substituted, if appropriate, by methyl or ethyl, R5 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, R6 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, R7 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylamino, ethylamino, dimethylamino or diethylamino, Y means the same group that is already bonded to the sulfur atom, or, when A means methyl, R also means acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methoxycarbonylcarbonyl, 2- bromoethoxycarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methylsulfonyl, ethylsulfonyl, phenylsulfonyl or tolylsulfonyl, G stands for -T-Ar'-O, Ar 1 means 1,2,4-thiadiazoldiyl, 1,3,4-thiadiazoldiyl, 1,2,4-oxadiazoldiyl, 1,3,4-oxadiazoldiyl or means pyridindiyl, pyrimidindiyl or 1,3,5-triazindiyl respectively substituted one or two times, in the same or in different ways entities by fluorine, by chlorine, by cyano, by methyl, by cyclopropyl, by methoxy, by methylthio, by trifluoromethyl, by difluoromethoxy, by trifluoromethoxy, by difluorochloromethoxy, T means a single bond, means oxygen, sulfur, -CH2-O- , CH2-S-, methylene, ethylene or propylene and L1, L2, L3 and L4 mean hydrogen, W means hydrogen, fluorine, cyano or thiocyanate and Z means methyl, ethyl, n- or i-propyl, n-, i- , s- or t-butyl, allyl, 2-buten-l-yl,
2- (1-methyl) -propyl, 2-methyl-2-buten-1-yl, propargyl or means pyridyl, pyrimidyl, thienyl, tetrahydrobenzofuranyl or especially phenyl, each optionally substituted one to three times, in the same or in different forms by amino, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, formyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, for trifluoromethyl, for substituted t-butyl tetrazole, for methoxy, for ethoxy, for n- or i-propoxy, for difluoromethoxy, for difluorochloromethoxy, for trifluoroethoxy, for trifluoromethoxy, for methoximinomethyl, for ethoximinoethyl, for methoximinoethyl, by ethoxymethyl or methylenedioxy or ethylenedioxy respectively double-bonded, respectively optionally substituted one to four times, in the same or different ways by fluorine, chlorine, methyl, trifluoromethyl or ethyl. 7. Compounds of the formula (I), according to claim 1, characterized in that A is hydrogen or methyl, or has the same meaning as R, R means methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, dichlorofluoromethylthio, trichloromethylthio, 2,2,2-trifluoroethylthio, methoxycarbonylthio, ethoxycarbonylthio, methylthiocarbonyl, ethylthiocarbonyl, n- or i-propylthiocarbonyl, phenylthio substituted, if appropriate, three times fluorine, chlorine, bromine, cyano, methyl or ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, by trifluoromethyl, by trifluoroethyl, by difluoromethoxy, by trifluoromethoxy, by difluorochloromethoxy, by trifluoroethoxy by methoxycarbonyl or by ethoxycarbonyl, -SY, -SN (R'R2), -CO-N (R3R4), - CN, -CH2-O-R5, -PO (OR6) R7, -PS (OR6) R7, where R1 signifies methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, R2 means met ilo, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxycarbonyl or ethoxycarbonyl, or together with R1, as well as with the nitrogen atom, with which they are bound, means pyrrolidino, piperidino, morpholino, optionally substituted by methyl or ethyl, R 3 is methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or optionally substituted phenyl one to three times, by fluorine, by chlorine, by bromine, by cyano, by methyl, by ethyl, by n- or i-propyl, by n-, i-, s- or t-butyl, by methoxy, by ethoxy, by n- i-propoxy, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, methoxycarbonyl or ethoxycarbonyl, R4 means methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfonyl, ethylsulphonyl, n- or i-propylsulfonyl, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, dichlorofluoromethylthio, trichloromethylthio or 2,2,2-trifluoroethylthio, or together with R3, as well as the nitrogen atom, to which they are linked, means pyrrolidino, piperidino, or morpholino, optionally substituted by methyl or ethyl, R5 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, R6 means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, R7 means methyl, ethyl, n- or i-propyl, n-, i-, s - or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylamino, ethylamino, dimethylamino, or diethylamino, Y means the same group that is bonded to the sulfur atom, or, when A means methyl, also means acetyl , propionyl, methoxycarbonyl, ethoxycarbonyl, methoxycarbonylcarbonyl, 2-bromoethoxycarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methylsulfonyl, ethylsulfonyl, phenylsulfonyl, or tolylsulfonyl, G stands for -C (= NO-R10) -C (R8) = NO-CH2- where R8 means methyl or cyclopropyl and R10 means hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or means benzyl optionally substituted by fl uo r, by chlorine, by bromine, by cyano, by methyl, by ethyl, by n- or i-propyl, by n-, i-, s- or t-butyl, by methoxy, by ethoxy, by n- or i -propoxi, by trifluoromethyl, by trifluoroethyl, by difluoromethoxy, by trifluoromethoxy, by difluorochloromethoxy or by trifluoroethoxy, L1, L2, L3 and L4 mean hydrogen, W means hydrogen, cyano or thiocyanate and Z means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, allyl, 2-buten-1-yl, 2-methyl-2-buten-1-yl or means pyridyl, pyrimidyl or especially phenyl substituted respectively in each case three times, in the same or in different ways, the possible substituents being preferably chosen from the following enumeration: 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, methylisulfinyl, ethylsulfinyl, methylisulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio , trifluoromethyl-sulphonyl or trifluoromethyl-sulfonyl, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, ethoxymethyl, methoxymethyl, ethoxymethyl, methylenedioxy, ethylenedioxy, respectively double-bonded, respectively substituted in the case of one to four times, in the same or in different ways by fluorine, chlorine, methyl, trifluoromethyl or by ethyl, or substituted tetra-t-butyl. 8. Compounds according to claim 1, characterize pcxque G means oxygen or means one of the following groupings, in which the left side is linked respectively with Z: -Q-CH2-, -C (R8) = NO-CH2- , -CH (R8) -ON = CH-, -C (R8) = NN = CH-, -C (= NOR, 0) -C (R8) = NO-CH2-, -C (= NO-RI0) -C (R8) -ON = CH-, -C (= NO-R10) -C (R8) -NN = CH- or T-Ar'-Q- where R8, R9, R10, T, Ar1 and Q, have the meanings indicated in claim 1. 9. Compounds of the formula (I) according to claim 1, characterize perqu A means methyl. 10. Compounds of the formula (I) according to claim 1, characterized by perch G means oxygen, -O-CH2-, -C (CH2) = N-O-CH2- or pyrimidinyloxy, optionally substituted by fluorine. 11. Compounds of the formula (I) according to claim 1, cararterized park Z means unsubstituted or mono or disubstituted phenyl. 12.- Agents containing extender and / or support materials as well as, if appropriate, surfactant products, characterized in that they have a content in at least one compound as described in claim 1. 13.- Procedure for the control of pests , characterized in that compounds are allowed to act on the pests and / or on their environment as defined in claim 1 or agents as defined in claim 12. 14. Use of the compounds as defined in claims 1 to 11 or of the agents as defined in claim 12, for the control of pests. 15. Process for obtaining agents characterized in that compounds such as those defined in claims 1 to 11 are mixed with extenders and / or surfactants. 16. Process for obtaining compounds of the formula (I), as defined in claim 1, characterized in that amides of the formula (II) are reacted wherein A, G, L1, L2, L3, L4, W and Z have the meanings indicated in claim 1, with an electrophilic reagent of the formula (III), RX (III) in which R has the indicated meaning in claim 1, and X means a dissociable group, optionally in the presence of a diluent and, if appropriate, in the presence of a base.
MXPA/A/2001/001768A 1998-08-17 2001-02-16 Methoximinophenylacetic acid amides MXPA01001768A (en)

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DE19837065.2 1999-06-05
DE19925780.9 1999-06-05

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MXPA01001768A true MXPA01001768A (en) 2001-12-04

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