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MXPA06010344A - Silylated carboxamides - Google Patents

Silylated carboxamides

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Publication number
MXPA06010344A
MXPA06010344A MXPA/A/2006/010344A MXPA06010344A MXPA06010344A MX PA06010344 A MXPA06010344 A MX PA06010344A MX PA06010344 A MXPA06010344 A MX PA06010344A MX PA06010344 A MXPA06010344 A MX PA06010344A
Authority
MX
Mexico
Prior art keywords
carbon atoms
alkyl
atoms
halogen
chlorine
Prior art date
Application number
MXPA/A/2006/010344A
Other languages
Spanish (es)
Inventor
Wachendorffneumann Ulrike
Dahmen Peter
Kuck Karlheinz
Elbe Hansludwig
Herrmann Stefan
Dunkel Ralf
Nico Greul Jorg
Ebbert Ronald
Hartmann Benoit
Klausener Alexander
Original Assignee
Bayer Cropscience Ag
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer Cropscience Ag filed Critical Bayer Cropscience Ag
Publication of MXPA06010344A publication Critical patent/MXPA06010344A/en

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Abstract

The invention relates to novel silylated carboxamides of formula (I), where M, L, R1, R2, R3, R and A have the meanings given in the description, several methods for production of said materials, the use thereof for the prevention of undesired microorganisms, novel intermediates and the production thereof.

Description

SILBATED CARBOXAMIDES FIELD OF THE INVENTION The present invention relates to novel silylated carboxamides, various processes for their preparation and their use for the control of undesirable microorganisms.
BACKGROUND OF THE INVENTION It is already known that a large number of carboxamides have fungicidal properties (see, for example, publications WO 03/080628, WO 03/010149, EP-A 0 589 301, EP-A 0 545 099). The activity of these products is good, however, it is not desirable, in some cases, for example, due to small application quantities. Hitherto, silylated carboxamides with heterocycles as an amide component have not been disclosed.
DETAILED DESCRIPTION OF THE INVENTION New silylated carboxamides of the formula (I) have now been found where Ms means a thiophene ring, pyridine ring, REF ..- 175609 pyrimidine, pyridazine or pyrazine monosubstituted, respectively, by Y1 or means a thiazole ring substituted by Y2, Y1 means hydrogen, fluorine, chlorine, bromine, methyl, iso-propyl, methylthio or trifluoromethyl, Y2 means hydrogen, fluorine, chlorine, bromine, methyl, methylthio or trifluoromethyl, L means a direct bond or means alkylene (alkanediyl), alkenylene (alkenodiyl) or alkynylene (alkynediyl) respectively straight chain or branched chain, optionally substituted, " - R 1 and R 2, independently of one another, are hydrogen, C 1 -C 8 alkyl, C 1 -C 8 alkoxy, C 1 -C 4 -alkoxy with 1 to 4 carbon atoms, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl or C 1 -C 6 -haloalkyl, R 3 is hydrogen, C 1-8 -alkyl, C 1-8 -alkoxy, alkoxy with 1 to 4 á carbon atoms-C 1 -C 4 -alkyl, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl, haloalkyl with 1 to 6 carbon atoms, haloalkenyl with 2 to 6 carbon atoms, haloalkynyl with 2 to 6 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, or means substituted phenyl or phenylalkyl, optionally, R means hydrogen, alkyl with 1 to 8 carbon atoms, alkylsulfinyl with 1 to 6 carbon atoms, alkylsulfonyl with 1 to 6 carbon atoms, alkoxy with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms, cycloalkyl with 3 to 8 carbon atoms; halogenalkyl with 1 to 6 carbon atoms, halogenalkylthio with 1 to 4 carbon atoms, halogenalkylsuifinyl with 1 to 4 carbon atoms, halogenalkylsulfonyl with 1 to 4 carbon atoms, haloalkoxy with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms, halogencycloalkyl with 3 to 8 carbon atoms with, respectively, 1 to 9 fluorine, chlorine and / or bromine atoms; formyl, formyl-C 1 -C 3 -alkyl, (C 1 -C 3 -alkyl) carbonyl-C 1 -C 3 -alkyl, (C 1 -C 3 -alkoxy) Caryl-C 1 -alkyl 3 carbon atoms; halogen- (C 1 -C 3 -alkyl) carbonyl-C 1 -C 3 -alkyl, halogen- (C 1 -C 3 -alkoxy) C 1 -C 3 -alkyl-alkyl with, respectively, 1 up to 13 fluorine, chlorine / bromine atoms; (C 1 -C 8 alkyl) carbonyl, (C 1 -C 8 alkoxy) carbonyl, (C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl) carbonyl, (C 3 -C a) -alkyl 8 carbon atoms) carbonyl; (halogenalkyl with 1 to 6 carbon atoms) carbonyl, (halogenalkoxy with 1 to 6 carbon atoms) carbonyl, (halogen-alkoxy with 1 to 4 carbon atoms-alkyl having 1 to 4 carbon atoms) carbonyl, (halogencycloalkyl with 3 to 8 carbon atoms) carbonyl with, respectively, 1 to 9 fluorine, chlorine and / or of bromine; or -C (= 0) C (= 0) R4, CONR5R6 or- -CH2NR7R8, R-4 means hydrogen, alkyl with 1 to 8 carbon atoms, alkoxy with 1 to 8 carbon atoms, alkoxy with 1 to 4 atoms carbon-alkyl with 1 to 4 carbon atoms, cycloalkyl with 3 to 8 carbon atoms; halogenalkyl with 1 to 6 carbon atoms, halogenalkoxy with 1 to 6 carbon atoms, halogen-alkoxy with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms, halogencycloalkyl with 3 to 8 carbon atoms with, respectively, 1 to 9 fluorine, chlorine and / or bromine atoms, R5 and R6 mean, independently of each other, respectively hydrogen, alkyl having 1 to 8 carbon atoms, alkoxy with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms, cycloalkyl with 3 to 8 carbon atoms; halogenalkyl with 1 to 8 carbon atoms, halogen-alkoxy with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms, halogencycloalkyl with 3 to 8 carbon atoms with, respectively, 1 to 9 fluorine, chlorine atoms and / or of bromine, R5 and R6 also form, together with the nitrogen atom, with which they are bound, a saturated heterocycle, with 5 to 8 ring atoms, optionally substituted one or more times, in the same or in different forms by halogen or by alkyl having 1 to 4 carbon atoms, the heterocycle containing 1 or 2 heteroatoms, which are not contiguous in the series consisting of oxygen, sulfur or NR9, may contain R7 and R8 independently of each other. yes, hydrogen, alkyl with 1 to 8 carbon atoms, cycloalkyl with 3 to 8 carbon atoms; halogenalkyl with 1 to 8 carbon atoms, halogencycloalkyl with 3 to 8 carbon atoms with, respectively, 1 to 9 fluorine, chlorine and / or bromine atoms, R7 and R8 also form together with the nitrogen atom, with which they are bound, a saturated heterocycle, with 5 to 8 ring atoms, substituted, if appropriate, one or more times, in the same or different ways by halogen or by alkyl with 1 to 4 carbon atoms, the heterocycle containing 1 or 2 heteroatoms, which are not contiguous in the series formed by oxygen, sulfur or NR9, can contain hydrogen or alkyl with 1 to 6 carbon atoms. It assigns the rest of the formula (Al) R means hydrogen, hydroxy, formyl, cyano, halogen, nitro, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, cycloalkyl with 3 to 6 carbon atoms , halogenalkyl with 1 to 4 carbon atoms, halogenalkoxy with 1 to 4 carbon atoms or halogenalkylthio with 1 to 4 carbon atoms with, respectively, 1 to 5 halogen atoms, aminocarbonyl or aminocarbonyl-alkyl with 1 to 4 carbon atoms , R11 means hydrogen, halogen, cyano, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, halogen with 1 to 4 carbon atoms or halogen alkylthio with 1 to 4 carbon atoms with, respectively, 1 to 5 halogen atoms, and R12 means hydrogen, alkyl having 1 to 4 carbon atoms, hydroxy-alkyl having 1 to 4 carbon atoms, alkenyl having 2 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, alkyl ilthio with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms, halogen with 1 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms-to uyl with 1 to 4 carbon atoms, halogenalkoxy with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms with, respectively, 1 to 5 halogen atoms, or means phenyl, or assigns the rest of the formula (A2) R13 and R14 mean, independently of each other, hydrogen, halogen, alkyl with 1 to 4 carbon atoms or halogen with 1 to 4 carbon atoms with 1 to 5 halogen atoms and R15 means halogen, cyano or alkyl with 1 to 4 atoms carbon, or halogenalkyl with 1 to 4 carbon atoms or halogenalkoxy with 1 to 4 carbon atoms with, respectively, 1 to 5 halogen atoms, or Assign the remainder of the formula (A3) R16 and R17 mean, independently of one another, hydrogen, halogen, alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms and R18 means hydrogen, alkyl with 1 to 4 carbon atoms o- halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, or assigns the remainder of the formula (A4) R 19 is hydrogen, halogen, hydroxy, cyano, alkyl having 1 to 6 carbon atoms, halogen with 1 to 4 carbon atoms, halogen with 1 to 4 carbon atoms or halogen with 1 to 4 carbon atoms with, respectively, 1 up to 5 halogen atoms, or Assign the rest of the formula (A5) R20 means halogen, hydroxy, cyano, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, halogenoalkyl with 1 to 4 carbon atoms, halogenalkylthio with 1 to 4 atoms of carbon or halogenalkoxy with 1 to 4 carbon atoms with, respectively, 1 to 5 halogen atoms and R21 means hydrogen, halogen, cyano, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, halogenalkyl with 1 to 4 carbon atoms, halogenalkoxy with 1 to 4 carbon atoms with, respectively, 1 to 5 halogen atoms, alkylsulfinyl with 1 to 4 carbon atoms or alkylsulfonyl with 1 to 4 Carbon atoms, or Assign the rest of the formula (A6) R22 means alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, or assigns the remainder of the formula (A7) R23 means alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, or assigns the remainder of the formula (A8) R24 and R25 signify, independently of one another, hydrogen, halogen, amino, alkyl with 1 to 4 carbon atoms or halogen with 1 to 4 carbon atoms with 1 to 5 halogen atoms and R26 means hydrogen, alkyl with 1 to 4 carbon atoms - or - halogenoalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, or Assign the remainder of the formula (A9) R27 and R28 denote, independently of one another, hydrogen, halogen, amino, nitro, alkyl having 1 to 4 carbon atoms or halogenalkyl having 1 to 4 carbon atoms with 1 to 5 halogen atoms and R29 means halogen, alkyl having 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, or Assign the rest of the formula (AlO) R 30 is hydrogen, halogen, amino, alkylamino eon 1 to 4 carbon atoms, di- (C 1 -C 4) alkyl amino, cyano, C 1 -C 4 -alkyl or haloalkyl with 1 to 4 atoms carbon with 1 to 5 halogen atoms and R31 means halogen, hydroxy, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, haloalkyl with 1 to 4 carbon atoms carbon or haloalkoxy with 1 to 4 carbon atoms with, respectively, 1 to 5 halogen atoms, or Assign the rest of the formula (All) R 32 is hydrogen, halogen, amino, alkylamino on 1 to 4 carbon atoms, di- (C 1 -C 4) alkyl, cyano, alkyl with 1 to 4 carbon atoms or halogen with 1 to 4 carbon atoms with 1 to 5 halogen atoms and R33 means halogen, alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, or assigns the remainder of the formula (A12) R34 means hydrogen or alkyl with 1 to 4 carbon atoms and R35 means halogen, alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, or assigns the remainder of the formula ( A13) R36 means hydrogen, halogen, alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, or assigns the remainder of the formula (A14) R37 means halogen, -hydroxy, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, halogenoalkyl with 1 to 4 carbon atoms, halogenalkylthio with 1 to 4 atoms carbon or halogenalkoxy with 1 to 4 carbon atoms with, respectively, 1 to 5 halogen atoms, or Assign the rest of the formula (A15) R38 means hydrogen, cyano, alkyl with 1 to 4 carbon atoms, halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, alkoxy with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms, hydroxy -alkyl with 1 to 4 carbon atoms, alkylsulfonyl with 1 to 4 carbon atoms, di (alkyl with 1 to 4 carbon atoms) aminosulfonyl, alkylcarbonyl with 1 to 6 carbon atoms or means substituted phenylsulfonyl or benzoyl respectively, in case given, R39 means hydrogen, halogen, alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, R40 means hydrogen, halogen, cyano, alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, R41 means hydrogen, halogen, alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, or. Assign the rest of the formula (Al6) R42 means halogen, alkyl having 1 to 4 carbon atoms or halogenalkyl having 1 to 4 carbon atoms with 1 to 5 halogen atoms, or Assigning the rest of the formula (A17) R3 means alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, R44 means alkyl with 1 to 4 carbon atoms, Q1 means S (sulfur), 0 (oxygen), SO, S02 or CH2, psignifies 0, 1 or 2, where R44 is the same or different, when p means 2. The compounds according to the invention can, if appropriate, be present as mixtures of the various possible isomeric forms, especially isomers sterics, such as, for example, the E and Z isomers, threo and erythro, as well as the optical isomers, if appropriate also of the -sutomers. Both the E isomers as well as the Z isomers are claimed, in the same way as the threo and erythro isomers, as well as the optical isomers, arbitrary mixtures of these isomers, as well as the possible tautomeric forms. In addition, it has been found that silylated carboxamides of the formula (I) are obtained, if a) carboxylic acid derivatives of the formula (II) are reacted wherein it has the meanings indicated above and X 1 means halogen or hydroxy, with an amine of the formula (III) wherein M, L, R 1, R 2, R 3 and R have the meanings given above, optionally in the presence of a catalyst, optionally in the presence of a condensing agent, optionally in the presence of an acceptor agent acid and, if appropriate, in the presence of a diluent, • or b) silylated carboxamides of the formula (Ia) are reacted wherein M, L, A, R1, R2 and R3 have the meanings given above with halides of the formula (IV) RA-X2 (IV) in which X2 means chlorine, bromine or iodine, RA means alkyl with 1 to 8 carbon atoms, alkylsulfinyl with 1 to 6 carbon atoms, alkylsulfonyl with 1 to 6 carbon atoms, alkoxy with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms, cycloalkyl with 3 to 8 carbon atoms; halogenalkyl with 1 to 6 carbon atoms, halogenalkylthio with 1 to 4 carbon atoms, halogenalkylsulfinyl with 1 to 4 carbon atoms, halogenalkylsulfonyl with 1 to 4 carbon atoms, halogenalkoxy with 1 to 4 carbon atoms - alkyl with 1 to 4 carbon atoms, halogencycloalkyl with 3 to 8 carbon atoms with, respectively, 1 to 9 fluorine atoms, chlorine and / or bromine, -formyl, formyl-alkylated with 1 to 3 carbon atoms, (alkyl with 1 to 3 carbon atoms) carbonyl-C 1 -C 3 -alkyl, (C 1 -C 3 -alkoxy) carbonyl-C 1 -C 3 -alkyl; halogen- (C 1 -C 3 -alkyl) carbonyl-C 1 -C 3 -alkyl, halogen- (C 1 -C 3 -alkoxy) C 1 -C 3 -alkyl-alkyl with, respectively, 1 up to 13 fluorine, chlorine and / or bromine atoms; (alkyl with 1 to 8 carbon atoms) carbonyl, (alkoxy with 1 to 8 carbon atoms) carbonyl, (C 1 -C 4 -alkyl with 1 to 4 carbon atoms) carbonyl, (C 3 -C 8 -cycloalkyl) carbonyl; (halogenalkyl with 1 to 6 carbon atoms) carbonyl, (halogenalkoxy with 1 to 6 carbon atoms) carbonyl, (halogen-alkoxy with 1 to 4 carbon atoms-alkyl having 1 to 4 carbon atoms) carbonyl, (halogencycloalkyl with 3 to 8 carbon atoms) carbonyl with, respectively, 1 to 9 fluorine, chlorine and / or of bromine; or -C (= 0) C (= 0) R4, -C0NR5R6 O -CH2NR7R8, where R4, R5, R6, R7 and R8 have the meanings indicated above, in the presence of a base and in the presence of a diluent. Finally, it has been found that the new silylated carboxamides of the formula (I) have very good microbicidal properties and that they can be used to combat undesirable microorganisms both in the protection of plants and also in the protection of materials . The silylated carboxamides, according to the invention, are defined, in general, by means of the formula (I). Following are preferred definitions of the remains of the formulas mentioned above and which will be cited below. These definitions are valid, in an equivalent way, for the final products of the formula (I) as well as for all the intermediate products. Preferably, M denotes one of the following heterocycles: the link being linked, marked with "*" with the amide, the link, marked with "# *" with the rest Z. Means, especially preferably, a heterocycle selected from Ml, M-2, M-3, M-4, M-5, M-7, M-8, M-9 and M-10 M denotes, very particularly preferably, a heterocycle selected from Ml, M-4, M-5, M-7, M-8, M-9 and M-10 M is particularly preferably the M 1 heterocycle, and M is also particularly preferably the heterocycle M-4. Particularly preferably, the heterocycle M-5 also denotes, in a particularly preferred manner, the heterocycle M-7, and M is also particularly preferably the M-8 heterocycle.
It also denotes, in a particularly preferred manner, the heterocycle M-9. It also denotes, in a particularly preferred manner, the heterocycle M-10. Preferably, Y 1 means hydrogen. Preferably, Y1 means, in the case where M means Ml, M-2 or M-3, in addition, chlorine, the chlorine being particularly preferably in the 5-position (Ml, M-2) or in the 3-position. (M-3). Preferably, Y1 means, in the case where M means _M-1, M-2 or M-3, in addition, fluorine, the fluorine being in a manner, especially preferentially in the 5-position (Ml, M-2) or position 3 (M-3). Preferably, Y 1 means, in the case where M means M 1, M 2 or M 3, in addition, methyl, with methyl being particularly preferably in the 5-position (M 1, M 2) or in the 3-position. M-3). Preferably, Y1 means, in the case where M means M-4, M-5, M-6 or M-7, in addition, fluorine, the fluorine being particularly preferably in the 6-position (M-4, M- 5) or in position 3 (M-6, M-7). Preferably, Y1 means, in the case where M means M-4, M-5, M-6 or M-7, in addition, chlorine, the chlorine being particularly preferably in the 6-position (M-4, M- 5) or in position 3 (M-6, M-7).
Preferably, Y1 means, in the case where M means M-4, M-5, M-6 or M-7, in addition, methyl, with methyl being particularly preferred in the 4-position (M-4) or position 3 (M-5, M-6, M-7). Preferably, Y1 means, in the case where M means M-8, in addition, methyl, the methyl being particularly preferably in the 3-position. Preferably, Y1 means, in the case where M means M-8, in addition, trifluoromethyl, the trifluoromethyl being particularly preferably in the 3-position. Preferably, Y 1 signifies, in the case where M means M-II, in addition, methyl, the methyl being particularly preferably in the 4-position. Preferably, Y 1 means , in the case where M means M-11, in addition, trifluoromethyl, the trifluoromethyl being particularly preferably in the 4-position. Preferably, Y 1 means, in the case where M means M-12, in addition, methyl, the methyl is particularly preferably in the 3-position. Preferably, Y 1 is, in the case where M means M-12, in addition, trifluoromethyl, the trifluoromethyl being particularly preferably in the 3-position.
Preferably, Y1 means, in the case where M means M-13, - in addition, methyl, the methyl being particularly preferably in the 3-position. Preferably, Y1 means, in the case where M means M-13, in addition , trifluoromethyl, the trifluoromethyl being particularly preferably in the 3-position. Preferably, Y 2 is hydrogen. Preferably, Y2 means fluorine. Preferably, Y2 means chlorine. Preferably, Y2 further means methyl. Preferably, Y2 means, in addition, trifluoromethyl. Preferably, L means a direct bond or means alkylene with 1 to 6 carbon atoms, alkenylene with 2 to 6 carbon atoms or alkynylene with 2 to 6 carbon atoms, straight chain or branched chain substituted, if appropriate, by halogen L is particularly preferably a direct bond or means -CH2-, - (CH2) 2-, - (CH2) 3-, -CH (Me) -, CH (Me) CH2-, -CH2CH (Me) -, -CH (Me) CH (Me) -, -C (Me2) CH2-, -CH (Me) - (CH2) 2-, -CH (Me) - (CH2) 3-, -CH = CH-, - C (Me) = CH- or -C = C-.
L is very particularly preferably - (CH2) 2-, - (CH2) 3-, -CH (Me) -, -CH (Me) CH2-, -CH (Me) - (CH2) 2-, -CH (Me) - (CH2) 3-, -CH = CH-, -C (Me) = CH- or -C = C-. Preferably, R1 and R2 mean, independently of each other, alkyl having 1 to 6 carbon atoms, alkoxy with 1 to 6 carbon atoms, alkoxy with 1 to 3 carbon atoms - alkyl with 1 to 3 carbon atoms or alkylthio with 1 to 3 carbon atoms-alkyl having 1 to 6 carbon atoms. R1 and R2 signify, independently of one another, particularly preferably methyl, ethyl, methoxy, ethoxy, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, methylthioethyl or ethylthioethyl. R.sub.1 and R.sub.2 independently of one another are very particularly preferably methyl, methoxy, methoxymethyl or methylthiomethyl. R 1 and R 2, respectively, are particularly preferably methyl. Preferably, R3 means alkyl with 1 to 6 carbon atoms, alkoxy with 1 to 6 carbon atoms, alkoxy with 1 to 3 carbon atoms-alkyl with 1 to 3 carbon atoms, alkylthio with 1 to 3 carbon atoms-alkyl with 1 to 3 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, phenyl or benzyl. R3 is particularly preferably methyl, ethyl, n- or iso-propyl, n-, sec-, iso- or tert-butyl, methoxy, ethoxy, n- or iso-propoxy, n-, sec-, iso- or tere. -butoxy, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, methylthioethyl, ethylthioethyl, cyclopropyl, phenyl or benzyl.
R3 very particularly preferably means methyl, ethyl, n- or iso-propyl, iso- or tere. -butyl, methoxy, iso-propoxy, iso- or tere. -butoxy, methoxymethyl, methylthiomethyl or phenyl. R3 particularly preferably means methyl, ethyl, n- or iso-propyl, iso- or tere. -butyl, methoxy, iso-propoxy, iso- or tere. -butoxi. R3 signifies, notably, methyl. Preferably, R represents hydrogen, alkyl having 1 to 6 carbon atoms, alkylsulfinyl with 1 to 4 carbon atoms, alkylsulfonyl with 1 to 4 carbon atoms, alkoxy with 1 to 3 carbon atoms-alkyl with 1 to 3 carbon atoms , cycloalkyl with 3 to 6 carbon atoms; halogenalkyl with 1 to 4 carbon atoms, halogenalkylthio with 1 to 4 carbon atoms, halogenalkylsulfinyl with 1 to 4 carbon atoms, halogenalkylsulfonyl with 1 to 4 carbon atoms, halogenalkoxy with 1 to 3 carbon atoms-alkyl with 1 at 3 carbon atoms, halogencycloalkyl having 3 to 8 carbon atoms with, respectively, 1 to 9 fluorine, chlorine and / or bromine atoms; formyl, formyl-C 1 -C 3 -alkyl, (C 1 -C 3 -alkyl) carbonylalkyl with 1 to 3 C atoms, (C 1 -C 3 -alkoxy) carbonyl-C 1 -C 3 -alkyl of carbon; halogen- (alkyl having 1 to 3 carbon atoms) carbonyl-alkylp with 1 to 3 carbon atoms, halogen- (alkoxy with 1 to 3 carbon atoms) carbonyl-alkyl with 1 to 3 carbon atoms with, respectively, 1 up to 13 fluorine, chlorine and / or bromine atoms; (C 1 -C 6 -alkyl) carbonyl, (C 1 -C 4 -alkoxy) carbonyl, C 1 -C 3 -alkoxy-C 1 -C 3 -alkyl, carbonyl, (C 3 -C 3 -alkyl) to 6 carbon atoms) carbonyl; (halogenalkyl with 1 to 4 carbon atoms) carbonyl, (halogenalkoxy with 1 to 4 carbon atoms) carbonyl, (halogen-alkoxy with 1 to 3 carbon atoms-alkyl having 1 to 3 carbon atoms) carbonyl, (halogencycloalkyl with 3 to 6 carbon atoms) carbonyl with, respectively, 1 to 9 fluorine, chlorine and / or bromine atoms; or -C (= 0) 0 (= 0) R4, -C0NR5R6 or -CH2NR7R8. It is particularly preferably hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tere.-butyl, pentyl or hexyl, methylsulfinyl, ethylsulfinyl, n- or iso-propylsulfinyl, n-, iso-, sec- or tere. -butylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or iso-propylsulfonyl, n-, iso-, sec- or tere. -butylsulfonyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl, trifluoromethyl, trichloromethyl, trifluoroethyl, difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, trifluoromethyl-sulphonyl, trifluoromethyl-sulfonyl, trifluoromethox imethyl; formyl, -CH2-CHO, - (CH2) 2-CH0, -CH2-CO-CH3, -CH2-CO-CH2CH3, -CH2-CO-CH (CH3) 2, - (CH2) 2-CO- CH3, - (CH2) 2-CO-CH2CH3, - (CH2) 2 -CO-CH (CH3) 2, -CH2-C02CH3, -CH2-C02CH2CH3, -CH2-C02CH (CH3) 2, - (CH2) 2 -C02CH3, - (CH2) 2-C02CH2CH3, - (CH2) 2-C02CH (CH3) 2, -CH2-CO-CF3, -CH2-CO-CCl3, -CH2-CO-CH2CF3, -CH2-C0-CH2CC13 , - (CH2) 2-CO-CH2CF3, - (CH2) 2-CO-CH2CCl3, -CH2-C02CH2CF3, -CH2-C02CF2CF3, -CH2-C02CH2CC13, -CH2-C02CC12CC13, - (CH2) 2-C02CH2CF3, - (CH2) 2-C02CF2CF3, - (CH2) 2-C02CH2CCl3 / - (CH2) 2-C02CC12CC13; methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, iso-propylcarbonyl, tert-butylcarbonyl, methoxycarbonyl, ethoxycarbonyl, tere. -butoxycarbonyl, "cyclopropylcarbonyl, trifluoromethylcarbonyl, trifluoromethoxycarbonyl, or -C (= 0) C (= 0) R4, -C0NR5R6 or -CH2NR7R8, R very particularly preferably means hydrogen, methyl, methoxymethyl, formyl, -CH2-CH0, - (CH2) 2-CH0, -CH2-C0-CH3, -CH2-CO-CH2CH3, -CH2-CO-CH (CH3) 2, -C (= 0) CHO, -C (= 0) C (= 0 CH3, -C (= 0) C (= 0) CH20CH3, -C (= 0) C02CH3, -C (= 0) C02CH2CH3 Preferably, R4 means hydrogen, alkyl with 1 to 6 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkoxy with 1 to 3 carbon atoms-alkyl with 1 to 3 carbon atoms, cycloalkyl with 3 to 6 carbon atoms; halogenalkyl with 1 to 4 carbon atoms, halogenalkoxy with 1 to 4 carbon atoms, halogen-alkoxy with 1 to 3 carbon atoms-alkyl with 1 to 3 carbon atoms, halogencycloalkyl with 3 to 6 carbon atoms with, respectively, 1 to 9 fluorine, chlorine and / or bromine atoms. R 4 is particularly preferably hydrogen, methyl, ethyl, n- or iso-propyl, tere. -butyl, methoxy, ethoxy, n- or iso-propoxy, tere. -butoxy, methoxymethyl, cyclopropyl; trifluoromethyl, trifluoromethoxy. Preferably, R5 and R6 independently denote hydrogen, alkyl having 1 to 6 carbon atoms, alkoxy with 1 to 3 carbon atoms-alkyl having 1 to 3 carbon atoms, cycloalkyl having 3 to 6 carbon atoms; halogenalkyl with 1 to 4 carbon atoms, halogen-alkoxy with 1 to 3 carbon atoms-alkyl with 1 to 3 carbon atoms, halogencycloalkyl with 3 to 6 carbon atoms with, respectively, 1 to 9 fluorine atoms, chlorine and / or bromine Preferably, R5 and R6 also form, together with the nitrogen atom, with which they are bound, a saturated heterocycle with 5 or 6 ring atoms, optionally substituted one to four times , in the same or in different forms by halogen or by alkyl having 1 to 4 carbon atoms, the hetrocycle containing 1 or 2 heteroatoms, which are not contiguous, may consist of the series formed by oxygen, sulfur or NR9. independently particularly preferably hydrogen, methyl, ethyl, n- or isopropyl, n-, iso-, 'sec- or tere.-butyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl; trifluoromethyl; , trichloromethyl, trifluoroethyl, t R5 and R6 form, together with the nitrogen atom, with which they are bound, particularly preferably a saturated heterocycle substituted, optionally one to four times, in the same or in different ways by fluorine. , by chlorine, by bromine or by methyl, of the series ~ formed by morpholine, thiomorpholine or piperazine, the piperazine being substituted on the second nitrogen atom by R 9. Preferably, R7 and R8 mean, independently of one another hydrogen, alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms; halogenalkyl with 1 to 4 carbon atoms, halogencycloalkyl with 3 to 6 carbon atoms with, respectively, 1 to 9 fluorine, chlorine and / or bromine atoms. Preferably, R7 and R8 also form, together with the nitrogen atom, with which they are bound, a saturated heterocycle with 5 or 6 ring atoms, optionally substituted one to four times, in the same or in different forms by halogen or by alkyl having 1 to 4 carbon atoms, the heterocycle comprising 1 or 2 more heteroatoms, non-contiguous, of the series formed by oxygen, sulfur or NR9. R7 and R8 signify independently, particularly preferably hydrogen, methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tere. -butyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl; trifluoromethyl, trichloromethyl, trifluoroethyl, trifluoromethoxymethyl. R7 and R8 also form, together with the nitrogen atom, with which they are bound, particularly preferably a saturated heterocycle, optionally substituted one to four times, in the same or in different ways by fluorine, by chlorine, by bromine or by methyl, of the series formed by morpholha, thiomorpholine or piperazine, the piperazine being substituted on the second nitrogen atom by R 9. Preferably, R9 means hydrogen or alkyl having 1 to 4 carbon atoms. R9 is particularly preferably hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tere. -butyl. Preferably, A means one of the residues indicated above Al, A2, A3, A4, A5, A8, A9, AlO, All, A12, A13, A14, A15 or Al7.
It particularly preferably denotes one of the residues indicated above Al, A2, A4, A5, A8, AlO, All, A12, Al3, A14, Al5 or Al7. It particularly particularly allocates the remainder Al. "- It also means, in a very particularly preferred way, the remainder A2, it also assigns, in a particularly preferred way, the remainder A4, it assigns, in addition, very especially The rest "A5" is also preferred, and A8 is very particularly preferred, it also allocates the AlO radical in a particularly preferred manner, it also assigns the All residue in a very particularly preferred manner. Very particularly preferably, the moiety Al2 also assigns, in a very particularly preferred way, the moiety Al3, it also particularly particularly allocates the moiety A14, it also particularly particularly allocates the moiety A15.
It also assigns, in a very particularly preferred manner, the rest Al7. Preferably, R10 means hydrogen, hydroxy, formyl, cyano, "fluoro, chloro, bromo, iodo, methyl, ethyl, iso-propyl, methoxy, ethoxy, methylthio, ethylthio, cyclopropyl, halogenalkyl with 1 to 2 carbon atoms, haloalkoxy with 1 to 2 carbon atoms with, respectively, 1 to 5 fluorine, chlorine and / or bromine, trifluor-paethylthio, difluoromethylthio, aminocarbonyl, aminocarbonylmethyl or aminocarbonylethyl atoms. R 10 - especially preferably hydrogen, hydroxy, formyl, fluorine, chlorine, bromine, iodine, methyl, ethyl, iso-propyl, - "methoxy, ethoxy, monofluoromethyl, monofluoroethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl, trichloromethyl, dichloromethyl, pentafluoroethyl , cyclopropyl, methoxy, ethoxy, trifluoromethoxy, difluoromethoxy, trichloromethoxy, methylthio, ethylthio, trifluoromethylthio or difluoromethylthio, R 10 very particularly preferably means hydrogen, hydroxy, formyl, fluorine, chlorine, bromine, iodine, methyl, ethyl, iso-propyl, methoxy, cyclopropyl, monofluoromyl, monofluoroethyl, difluoromethyl, dichloromethyl, trifluoromethyl, difluorochloromethyl, trichloromethyl, -CHFCH3 or difluoromethoxy, R10 particularly preferably means hydrogen, hydroxy, formyl, chloro, methyl, ethyl, methoxy, cyclopropyl, monofluoromethyl, difluoromethyl, dichloromethyl, trifluoromethyl, -CHFCH3 or difluoromethoxy. Preferably, R11 means hydrogen fluorine, chlorine, bromine, iodine, methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, halogenalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms, R 11 means especially preferred hydrogen, fluorine, chlorine, bromine, iodine, methyl or -CHFCH3. R 11 very particularly preferably means hydrogen, fluorine, chlorine or methyl. Preferably, R12 means hydrogen, methyl, ethyl, n-propyl, iso-propyl, halogenalkyl with 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms, hydroxymethyl, hydroxyethyl, cyclopropyl, cyclopentyl , R12 is particularly preferably hydrogen, methyl, ethyl, iso-propyl, trifluoromethyl, difluoromethyl, hydroxymethyl, hydroxyethyl or phenyl, R12 very particularly preferably hydrogen, methyl, trifluoromethyl or phenyl. particularly preferred methyl R.sup.13 and R.sup.14 independently of each other preferably means hydrogen, fluorine, chlorine, bromine, methyl, ethyl or halogenoalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms. and R 14 are independently, particularly preferably, hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl or Chloromethyl R13 and R14 mean independently, very particularly preferably hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl or trichloromethyl. R13 and R14 particularly preferably mean, respectively, hydrogen. Preferably, R15 means fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, halogenalkyl having 1 to 2 carbon atoms or halogenalkoxy having 1 to 2 carbon atoms with, respectively, 1 to 5 fluorine, chlorine and / or or bromine. R 15 is particularly preferably fluorine, chlorine, bromine, iodine, cyano, methyl, trifluoromethyl, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy or trichloromethoxy. R 15 very particularly preferably means fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl or trifluoromethoxy. R 15 is particularly preferably chlorine, bromine, iodine, trifluoromethyl or methyl.
Preferably, R 16 and R 17 mean, independently of one another, hydrogen, fluorine, chlorine, bromine, methyl, ethyl or halogenoalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms. R 16 and R 17 signify independently, particularly preferably hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl or trichloromethyl. R 16 and R 17 mean independently, very particularly preferably hydrogen, fluorine, chlorine, bromine or methyl. R16 and R17, particularly preferably, mean hydrogen. Preferably, R18 is hydrogen, methyl, ethyl or haloalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms. R18 is particularly preferably hydrogen, methyl or trifluoromethyl. R18 very particularly preferably means methyl. Preferably, R19 means hydrogen, fluorine, chlorine, bromine, iodine, hydroxy, cyano, alkyl with 1 to 4 carbon atoms, halogen with 1 to 2 carbon atoms, halogen with 1 to 2 carbon atoms or halogen with 1 to 2 carbon atoms. carbon atoms with, respectively, 1 to 5 fluorine, chlorine and / or bromine atoms. R 19 is particularly preferably hydrogen, fluorine, chlorine, bromine, iodine, hydroxy, cyano, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tere. -butyl, difluoromethyl, trifluoromethyl, difluorochloromethyl, trichloromethyl, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy, trichloromethoxy, trifluoromethylthio, difluoromethylthio, difluorochloromethylthio or trichloromethylthio. R19 ~ very particularly preferably means "hydrogen, fluorine, chlorine, bromine, iodine, methyl, difluoromethyl, trifluoromethyl or trichloromethyl, R19 particularly preferably means bromine, iodine, methyl, difluoromethyl or trifluoromethyl. Preferably, R20 means fluorine, chlorine , bromine, iodine, hydroxy, cyano, alkyl with 1 to 4 carbon atoms, methoxy, ethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, halogenalkyl with 1 to 2 carbon atoms or halogenalkoxy with 1 to 2 carbon atoms with, respectively 1 to 5 fluorine, chlorine and / or bromine atoms R20 is particularly preferably fluorine, chlorine, bromine, iodine, hydroxy, cyano, methyl, ethyl, n-propyl, iso-propyl, n-butyl, isobutyl, sec-butyl, tere. -butyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, trichloromethyl, methoxy, ethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy or triclo R20 is very particularly preferably fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl. Preferably, R21 means hydrogen, fluorine, chlorine, bromine, iodine, cyano, alkyl having 1 to 4 carbon atoms, methoxy, ethoxy, methylthio, ethylthio, halogenalkyl with 1 to 2 carbon atoms or halogenalkoxy with 1 to 2 carbon atoms with, respectively, 1 to 5 fluorine, chlorine and / or bromine atoms, alkylsulfinyl with 1 to 2 carbon atoms or alkylsulfonyl with 1 to 2 carbon atoms. R21 is particularly preferably hydrogen, fluorine, chlorine, bromine, iodine, cyano, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tere. -butyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, trichloromethyl, methoxy, ethoxy, methylthio, ethylthio, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy, trichloromethoxy, methylsulphinyl or methylsulfonyl. R21 very particularly preferably means hydrogen, fluorine, chlorine, bromine, iodine, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tere. -butyl, trifluoromethyl, difluoromethyl, trichloromethyl, methylsulfinyl or methylsulfonyl. R21 is particularly preferably hydrogen. Preferably, R22 means methyl, ethyl or halogenoalkyl with 1 to 2 carbon atoms, with 1 to 5 fluorine atoms, chlorine and / or bromine. R22 is particularly preferably methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or p-trichloromethyl. R22 means "very particularly preferably" means methyl, trifluoromethyl, difluoromethyl or trichloromethyla "" Preferably, R23 means methyl, ethyl or haloalkyl "with 1 to 2 carbon atoms with 1 to 5 fluorine atoms, chlorine and bromine R 23 is particularly preferably methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl R 23 very particularly preferably methyl, trifluoromethyl, difluoromethyl or trichloromethyl Preferably, R 24 and R 25 are independently hydrogen, fluorine, chlorine, bromine, amino, methyl, ethyl or halogenoalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms R 24 and R 25 signify independently, particularly preferably hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl. difluorochloromethyl or trichloromethyl. R 24 and R 25 mean, independently of one another, very particularly preferably hydrogen, fluorine, chlorine, bromine or methyl. R 24 and R 25 are particularly preferably hydrogen. Preferably, R26 means hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl or halogenalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms. R 26 is particularly preferably hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl. R 26 very particularly preferably means hydrogen, fluorine, chlorine, bromine, methyl or trifluoromethyl. R 26 is particularly preferably methyl or trifluoromethyl. Preferably, R 27 and R 28 mean, independently of one another, hydrogen, fluorine, chlorine, bromine, amino, nitro, methyl, ethyl or halogenoalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms. R 27 and R 28 signify independently, particularly preferably hydrogen, fluorine, chlorine, bromine, nitro, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl. R 27 and R 28 signify independently, very particularly preferably hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl. R 27 and R 28, particularly preferably, mean hydrogen. Preferably, R29 means fluorine, chlorine, bromine, methyl, ethyl or halogenoalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms. R 29 is particularly preferably fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl. R29 very particularly preferably means fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl. R29 is particularly preferably methyl. Preferably, R 30 is hydrogen, fluorine, chlorine, bromine, amino, alkylamino with 1 to 4 carbon atoms, di (C 1-4 -alkyl) amino, cyano, methyl, ethyl or haloalkyl with 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms. R 30 is particularly preferably hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl. R 30 very particularly preferably means hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, methyl, trifluoromethyl, difluoromethyl or trichloromethyl. R 30 is particularly preferably amino, methylamino, dimethylamino, methyl or trifluoromethyl. Preferably, R31 means fluorine, chlorine, bromine, hydroxy, methyl, ethyl, methoxy, ethoxy, cyclopropyl, halogenalkyl with 1 to 2 carbon atoms or halogenalkoxy with 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine. R 31 is particularly preferably fluorine, chlorine, bromine, hydroxy, methyl, ethyl, methoxy, ethoxy, cyclopropyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl. R 31 very particularly preferably means fluorine, chlorine, bromine, hydroxy, methyl, methoxy, cyclopropyl, trifluoromethyl, difluoromethyl or trichloromethyl. Preferably, R3 means hydrogen, fluorine, chlorine, bromine, amino, alkylamino with 1 to 4 carbon atoms, di (C1 to C4 alkyl) amino, cyano, methyl, ethyl or haloalkyl with 1 to 2 carbon atoms , with 1 to 5 fluorine, chlorine and / or bromine atoms. R32 is particularly preferably hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl. R32 very particularly preferably means hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, methyl, trifluoromethyl, difluoromethyl or trichloromethyl. R 32 is particularly preferably amino, methylamino, dimethylamino, methyl or trifluoromethyl. Preferably, R33 means fluorine, chlorine, bromine, methyl, ethyl or halogenalkyl having 1 to 2 carbon atoms, with 1 to 5 fluorine, chlorine and / or bromine atoms, R33 is particularly preferably fluorine, chlorine. , bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl R 33 very particularly preferably means fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl R 33 is particularly preferably methyl, trifluoromethyl or difluoromethyl. R34 is hydrogen, methyl or ethyl, R34 is particularly preferably methyl, preferably R35 is fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl or difluoromethyl.
R 35 is particularly preferably fluorine, chlorine, methyl, trifluoromethyl or difluoromethyl. Preferably, R36 means hydrogen, fluorine, chlorine, bromine, methyl, ethyl or halogenoalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms. R 36 is particularly preferably hydrogen, fluorine, chlorine, bromine, methyl or trifluoromethyl. Preferably, R37 means fluorine, chlorine, bromine, iodine, hydroxy, alkyl with 1 to 4 carbon atoms, methoxy, ethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, halogenalkyl with 1 to 2 carbon atoms or halogenalkoxy with 1 to 2 atoms of carbon with, respectively, 1 to 5 fluorine, chlorine and / or bromine atoms. R 37 is particularly preferably fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tere. -butyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, trichloromethyl. R 37 very particularly preferably means fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl. Preferably, R38 means hydrogen, methyl, ethyl, halogenalkyl with 1 to 2 carbon atoms, with 1 to 5 fluorine, chlorine and / or bromine atoms, alkoxy with 1 to 2 carbon atoms-alkyl with 1 to 2 atoms of carbon, hydroxymethyl, hydroxyethyl, methylsulfonyl or dimethylaminosulfonyl. R38 is particularly preferably hydrogen, methyl, ethyl, trifluoromethyl, methoxymethyl, ethoxymethyl, hydroxymethyl or hydroxyethyl. R38 very particularly preferably means methyl or methoxymethyl. Preferably, R39 means hydrogen, fluorine, chlorine, bromine, methyl, ethyl or halogenoalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms. R 39 is particularly preferably hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl or trichloromethyl. R39 very particularly preferably means hydrogen or methyl. Preferably, R40 means hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, iso-propyl or halogenalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms. R 40 is particularly preferably hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, iso-propyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl. R 40 very particularly preferably means hydrogen, iodine, methyl or trifluoromethyl. Preferably, R41 means hydrogen, fluorine, chlorine, bromine, methyl, ethyl or halogenoalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms.
R41 is particularly preferably hydrogen, fluorine, chlorine, bromine, iodine, methyl or trifluoromethyl. R41 very particularly preferably means hydrogen or trifluoromethyl. Preferably, R42 means fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, iso-propyl, trifluoromethyl or difluoromethyl. R 42 is particularly preferably fluorine, chlorine, bromine, iodine, methyl, ethyl or trifluoromethyl. Preferably, R43 means methyl, ethyl or haloalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms. R43 is particularly preferably methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl. Preferably, R44 means methyl or ethyl. R44 is particularly preferably methyl. Preferably, Q1 means S (sulfur), S02 or CH2. Q1 is particularly preferably S (sulfur) or CH2 Q1 very particularly preferably means S (sulfur). Preferably, p means 0 or 1.
P is particularly preferably 0. The compounds of the formula (I), in which R 1 denotes hydrogen, should be mentioned. The compounds of the formula (I), in which R 1 means formyl, should be mentioned. The compounds of the formula (I), in which R 4 means -C (= 0) C (= 0) R 5, R 5, having the meanings given above, should also be mentioned. The compounds of the formula (I), in which A means Al, should be mentioned. The compounds of the formula (I), in which M means M-1, should be mentioned. - The compounds of the formulas must also be mentioned in which, respectively Y1, Y2, L, R1, R2, R3, R and A have the general, preferred, especially preferred and very particularly preferred meanings, etc., indicated above. The saturated or unsaturated hydrocarbon radicals, such as alkyl or alkenyl, can be, even in combination with heteroatoms, such as, for example, alkoxy, as far as possible, respectively straight-chain or branched chain. The residues, if any substituted, can be monosubstituted or polysubstituted, the substituents being the same or different in the case of polysubstitutions. Remains substituted by halogen, such as, for example, haloalkyl, are monohalogenated or polyhalogenated. In the case of polyhalogenations, the halogen atoms may be the same or different. In this case halogen means fluorine, chlorine, bromine and iodine, especially fluorine, chlorine and bromine. However, the definitions or explanations of the residues given above in a general manner or in the indicated preferred ranges may be combined arbitrarily with one another, ie between the respective ranges and the preferred ranges. These are valid for the final products as well as, correspondingly, for the starting products and the intermediate products. The cited definitions can be combined arbitrarily with each other. In addition, individual definitions can also be deleted. Preferred, especially preferred or very particularly preferred are the compounds of the formula (I), which carry, respectively, the substituents mentioned as preferred, especially preferred or very particularly preferred. Explanations of the procedures and intermediate products Procedure (a) If 2-chlorobenzoyl chloride is used and the. { 2- [l-Methyl-2- (trimethylsilyl) ethyl] -3-thienyl} amine as starting products, the process (a), according to the invention, may be represented by means of the following formula scheme: The carboxylic acid derivatives which are necessary as starting materials for carrying out the process (a) according to the invention are defined, in general, by means of the formula (II). In this formula (II), A is preferably, particularly preferably or very particularly preferably those meanings, which have already been cited as preferred, as being particularly preferred or very particularly preferred in connection with the description of the compounds of the formula (I) - according to the invention for A. Preferably X1 means chlorine, bromine or hydroxy. The carboxylic acid derivatives of the formula (II) are known "and / or can be prepared according to known processes (see publications WO 93/11117, EP-A 0 545 099, EP-A 0 589 301 and EP- No. 0 589 313) The amines, which are also necessary as starting materials for carrying out the process (a), according to the invention, are defined, in general, by means of the formula (III). , M, L, R1, R2 and R3 preferably have, preferably or very particularly preferably those meanings which have already been indicated as being preferred, as being especially preferred or very particularly preferred in connection with the description of the compounds of the formula (I) according to the invention.
The amines of the formula (III) are new The amines of the formula (Ill-a) L1 means alkylene (alkanediyl), M, R1, R2 and R3 have the meanings indicated above, are obtained, for example, if c) protected amines of the formula (V) are reacted wherein M and R have the meanings given above, in a first step with an iodination agent (for example iodine) if appropriate in the presence of a diluent (for example tetrahydrofuran) and, if appropriate, in the presence of a compound organometallic (for example n-butyl lithium), and the iodides, obtained in this way, of the formula (VI) wherein M and R have the meanings indicated above, they are reacted, in a second step with compounds of the formula (VII) wherein L2 means alkenylene (alkenodiyl) or alkynylene (alkynediyl), R1 ,. R2 and R3 have the meanings given above, in the presence of a base (for example triethylamine), in the presence of a catalyst [for example bis (triphenylphosphine) palladium (II) chloride] and, if appropriate, in the presence of another agent reaction aid [for example cuprous iodide (I)], and the protected amines, thus obtained, of the formula (VIII) wherein M, L2, R1, R2 and R3 have the meanings given above, are hydrogenated in a third step in the presence of a catalyst (for example palladium) and, if appropriate, in the presence of a diluent (for example methanol) , and the protected amines, obtained in this way, of the formula (IX) wherein M, L, R1, R2 and R3 have the meanings indicated above, - ~ are reacted, in a fourth step, * in the presence of an acid (for example trifluoroacetic acid) and, if appropriate, in the presence of a diluent (see, also, the obtaining examples). The amines of the formula (Ill-b) are obtained wherein M, L1, R1, R2, R3 and RA have the meanings indicated above, if amines of the formula (Ill-a) are reacted with halides of the formula (IV) R-X2 (IV) in which X2 and RA have the meanings indicated above, according to procedure (b). The amines of the formula (Ill-b) can also be obtained if, first, the amines of the formula (IX) are reacted with halides of the formula (IV) and then the protective groups are removed [according to step 4 of procedure (c)]. The amines of the formula (III-c) are obtained wherein M, L2, R1, R2 and R3 have the meanings indicated above, if the protected amines of the formula (VIII) are deprotected [according to step 4 of process (c)]. The amines of the formula (Ill-d) are obtained wherein M, L1, R1, R2, R3 and RA have the meanings indicated above, if amines of the formula (Ill-c) are reacted with halides of the formula (IV) in a manner analogous to that of the process (b) ) or if protected amines of the formula (VIII) are reacted with halides of the formula (IV) and then the protective groups are removed [according to step 4 of process (c)]. In addition, the amines of the formula (III) can be obtained in a manner analogous to that described in the WO publication 03/080628. In the formulas (Ill-a), (Ill-b), (III-c), (Iir-d), (VII), (VIII) and (IX), L1 and L2 preferably have, with particular preference and very particularly preferably the meanings indicated for L, respectively, preferably, particularly preferably and very particularly preferably. Procedure (b) If, for example, 5-fluoro-l, 3-dimethyl-N- is used. { 2- [2- (Trimethylsilyl) ethyl] -3-thienyl} -lH-pyrazole-4-carboxamide and the chloro (oxo) ethyl acetate as starting materials, the development of process (b), according to the invention, can be represented by means of the following formula scheme: The silylated carboxamides, which are necessary as starting materials for carrying out process (b) according to the invention, are defined, in general, by means of formula (I-a). In this formula (Ia), M, L, A, R1, R2 and R3 preferably have, preferably or very particularly preferably, those meanings which have already been indicated as preferred, as being particularly preferred or especially preferred for these residues in relation to the description of the compounds of the formula (I) according to the invention. - The silylated carboxamides of the formula (I-a) are, -also, compounds according to the invention and also constitute an object of this application. These can be prepared according to process (a) according to the invention (with R = hydrogen). The halides, which are also necessary as starting materials for carrying out process (b) according to the invention, are defined by means of formula (IV). Preferably, RA means alkyl with 1 to 6 carbon atoms, alkylsulfinyl with 1 to 4 carbon atoms, alkylsulfonyl with 1 to 4 carbon atoms, alkoxy with 1 to 3 carbon atoms-alkyl with 1 to 3 carbon atoms, cycloalkyl with 3 to 6 carbon atoms; halogenalkyl with 1 to 4 carbon atoms, halogenalkylthio with 1 to 4 carbon atoms, halogenalkylsuifinyl with 1 to 4 carbon atoms, halogenalkylsulfonyl with 1 to 4 carbon atoms, halogenalkoxy with 1 to 3 carbon atoms - alkyl with 1 at 3 carbon atoms, halogencycloalkyl having 3 to 8 carbon atoms with, respectively, 1 to 9 fluorine, chlorine and / or bromine atoms; formyl, formyl-C 1 -C 3 -alkyl, (C 1 -C 3 -alkyl) carbony1-C 1 -C 3 -alkyl, C 1 -C 3 -alkoxycarbonyl-alkyl with 1 a 3 carbon atoms; halogen- (alkyl with 1 to 3 carbon atoms) carbonylalkyl with 1 to 3 carbon atoms, halogen- (alkoxy with 1 to 3 carbon atoms) carbonyl-alkyl with 1 to 3 carbon atoms with, respectively, 1 to 13 fluorine, chlorine and / or bromine atoms; (C 1 -C 6 alkyl) carbonyl, (C 1 -C 4 alkoxy) carbonyl, (C 1 -C 3 -alkoxy-C 1 -C 3 -alkyl) carbonyl, (C 3 -C 3) -alkyl 6 carbon atoms) carbonyl; (halogenalkyl with 1 to 4 carbon atoms) carbonyl, (halogenalkoxy with 1 to 4 carbon atoms) carbonyl, (halogen-alkoxy with 1 to 3 carbon atoms-alkyl with -1 to 3 carbon atoms) carbonyl, (halogencycloalkyl) with 3 to 6 carbon atoms) carbonyl with, respectively, 1 to 9 fluorine, chlorine and / or bromine atoms; or -C (= 0) C (= 0) R4, -C0NR5R6 or -CH2NR7R8. Particularly preferably, RA means methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tere. -butyl, pentyl or hexyl, methylsulfinyl, ethylsulfinyl, n- or iso-propylsulfinyl, n-, iso-, sec- or tere. butylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or isopropylsulfonyl, n-, iso-, sec-. or tere. -butylsulfonyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl, trifluoromethyl, trichloromethyl, trifluoroethyl, difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, trifluoromethyl-sulphonyl, trifluoromethyl-sulfonyl, trifluoromethoxymethyl; formyl, -CH2-CHO, ~ (CH2) 2-CHO, -CH2-CO-CH3, -CH2-CO-CH2CH3, -CH2-CO-CH (CH3) 2, - (CH2) 2-CO-CH3, - (CH2) 2-CO-CH2CH3, - (CH2) 2-CO-CH (CH3) 2, -CH2-C02CH3, -CH2-C02CH2CH3, -CH2-C02CH (CH3) 2, - (CH2) 2-C02CH3 , - (CH2) 2-C02CH2CH3, - (CH2) 2-C02CH (CH3) 2, -CH2-CO-CF3, -CH2-C0-CC13, -CH2-C0-CH2CF3, -CH2-C0-CH2CC13, - (CH2) 2 ~ CO-CH2CF3, - (CH2) 2-CO-CH2CCl3, -CH2-C02CH2CF3, -CH2-C02CF2CF3, -CH2-C02CH2CC13, -CH2-C02CC12CC13, - (CH2) 2-C? 2CH2CF3, - (CH2) 2-C02CF2CF3, - (CH2) 2-C02CH2CCl3, - (CH2) 2-C02CC12CC13; methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, iso-propylcarbonyl, tere. -butylcarbonyl, methoxycarbonyl, ethoxycarbonyl, tere. -butoxycarbonyl, cyclopropylcarbonyl; trifluoromethylcarbonyl, trifluoromethoxycarbonyl, oC (= 0) C (= 0) R4, -C0NR5R6 or -CH2? R7R8. Very particularly preferably, RA means methyl, methoxymethyl, formyl, -CH2-CH0, - (CH2) 2 -CH0, -CH2-CO-CH3, -CH2-C0-CH2CH3, -CH2-CO-CH (CH3) 2, -C (= 0) CHO, -C (= 0) C (= 0) CH3, -C (= 0) C (= 0) CH2OCH3, -C (= 0) C02CH3, -C (= 0) C02CH2CH3. Preferably, X2 means chlorine or bromine. The halides of the formula (IV) are known. Conditions of reaction z As diluents for. In carrying out the process (a), according to the invention, all inert organic solvents are suitable. 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 or amides, such as N, N-dimethylformamide,? N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphorotriamide. Process (a), 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, acetates, carbonates or bicarbonates of alkaline earth metals or alkali metals, such as, for example, sodium hydride, sodium amide, sodium methylate, sodium ethylate, tert. -butyrate of potassium, sodium hydroxide, potassium hydroxide, ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium bicarbonate, baking soda sodium or ammonium carbonate as well as tertiary amines, such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, N, N-dimethyl-benzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N, N-dimethylaminopyridine, diazabicyclooctane ( DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU). The process (a), according to the invention, is carried out, if appropriate, in the presence of a suitable condensation agent. As such, all the condensation agents which are usually usable for this type of amidation reactions are suitable. Acyl halogenide formers such as phosgene, phosphorus tribromide, phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride or thionyl chloride can be mentioned.; anhydride formers such as ethyl chloroformate, methyl chloroformate, isopropyl chloroformate, isobutyl chloroformate or methanesulfonyl chloride; carbodiimides, such as N, N'-dicyclohexylcarbodiimide (DCC) or other conventional condensing agents, such as phosphorus pentoxide, polyphosphorous acid, α, N'-carbonyldiimidazole, 2-ethoxy-β-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ), triphenylphosphine / "carbon tetrachloride or bromotropyrrolidinophosphonium hexafluorophosphate The process (a), according to the invention, is carried out, if appropriate, in the presence of a catalyst.
In an exemplary way. there may be mentioned 4-dimethylaminopyridine, 1-hydroxy-benzotriazole or dimethylformamide. The reaction temperatures in carrying out the process (a), according to the invention, can vary within wide limits. In general, temperatures are from 0 ° C to 150 ° C, preferably at temperatures from 0 ° C to 80 ° C. In carrying out the process (a) according to the invention, for the preparation of the compounds of the formula (I), per mole of the carboxylic acid derivative of the formula (II), generally 0.2 is used. up to 5 moles, preferably from 0.5 to 2 moles of aniline derivative of the formula (III). Suitable diluents in the process (b) according to the invention are all customary inert organic solvents. These include, for example, aliphatic, alicyclic or aromatic hydrocarbons, such as petroleum ether, hexane, heptane, cyclohexane; methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as for example chlorobenzene, dichlorobenzene, dichloromethane, chloroform, tetrachloromethane, dichloroethane, or trichloroethane; ethers, such as diethyl ether, diisopropyl ether, methyl tert. -butyl ether, methyl-tert. -amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole or amides, such as N, N-dimethylformamide, N, N-dimethylacetamide,? -methylformanilide, N-methylpyrrolidone or hexamethylphosphorotriamide. Process (b), according to the invention, is carried out in the presence of a base. As such, all inorganic or organic bases are suitable. These preferably include hydrides, hydroxides, amides, alcoholates, acetates, carbonates or bicarbonates of alkali metals or alkaline earth metals, such as, for example, sodium hydride, sodium amide, sodium methylate, sodium ethylate, tere . - potassium butylate, sodium hydroxide, potassium hydroxide, ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate or carbonate of cesium, as well as tertiary amines such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, N, N-dimethyl-benzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (DB?) or diazabicycloundecene (DBU). The reaction temperatures in carrying out the process (b), according to the invention, can vary within wide limits. In general it is -worked at temperatures from 0SC to 1502C, preferably at temperatures from 20-C to 1102C. To carry out the process (b) according to the invention for the preparation of the compounds of the formula (I), per mol of the isopenty1carboxamide of the formula (Ia), generally from 0.2 to 5 mol, are used. preferably from 0.5 to 2 moles of halide of the formula (IV). When nothing else is said, all the procedures according to the invention will be carried out, in general, under normal pressure. However, it is also possible to work under higher pressure or at lower pressure, generally between 0.1 bar and 10 bar.
The products according to the invention have a potent microbicidal effect and can be used in practice to combat undesirable microorganisms, such as fungi and bacteria, in the protection of plants and in the protection of materials. The fungicidal agents can be used in the protection of plants for the fight against plasmodioforomycetes, oomycetes, chytridiomycetes, zygomycetes, ascomycetes, basidiomycetes and deuteromycetes. - Bactericidal agents can be used in the protection of plants to combat "pseudomonadaceos, rhizobiaceous, enterobacteriaceous, corynebacteriaceous and streptomycetaceous." Some pathogens of fungal and bacterial diseases can be cited by way of example, but without limitation, that fall within the scope of the invention. the general definitions listed above: types of Xanthomonas, such as for example Xanthomonas campestris pv. oryzae; Pseudomonas types, such as, for example, Pseudomonas syringae pv. lachrymans; Erwinia types, such as, for example, Erwinia amylovora; Pythium types, such as for example Pythium ultimun; types of Phytophthora, 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; Bremia types, such as, for example, Bremia lactucae; Peronospora types, such as, for example, Peronospora pisi or P. brassicae; Erysiphe types, such as for example Erysiphe graminis; Sphaerotheca types, such as for example Sphaerotheca fuliginea; Podosphaera types, such as for example Podosphaerá leucotricha; Venturia types, such as, for example, Venturia inaequalis; types of Pyrenophora, such as, for example, Pyrenophora teres or P. gramínea; (form of conidia, Drechslera, synonym: Helminthosporium); types of Cochliobolus, such as, for example, Cochliobolus sativus (conidia form, Drechslera, synonym: Helminthosporium); Uromyces types, such as, for example, Uromyces appendiculatus; Puccinia types, such as Puccinia recondita; Sclerotinia types, such as, for example, Sclerotinia sclerotiorum; types of Tilletia, such as for example Tilletia caries; types of Ustilago, such as, for example, Ustilago nuda or Usti1ago avenae; Pellicularia types, such as, for example, Pellicularia s sakii; types of Pyricularia, 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 Leptdsphaeria nodorum; ~ types of Cercospora, such as for example Cercospora canescens; types of Alternaria, such as for example Alternaria brassicae; types of Pseudocercosporella, such as for example Pseudocercosporella herpotrichoides, types of Rhizoctonia, such as, for example, Rhizoctonia solani The active compounds according to the invention also have a potent reinforcing effect on plants, which are therefore suitable for mobilizing the resistance forces characteristic of plants against attack by plants. Undesirable microorganisms In this context it will be understood by plant reinforcing products (resistance inducers) those substances that are capable of stimulating the immune system of plants in such a way that, the treated plants develop a broad resistance against microorganisms when produce a subsequent inoculation with these microorganisms We are undesirable. It should be understood as "undesirable microorganisms, in the present case, phytopathogenic fungi, bacteria and viruses." The products according to the invention can be used, therefore, to generate resistance in plants, within a certain period of time, from of the treatment, against the attack due to the aforementioned pathogens The time lapse, within which resistance is caused, extends, in general, from 1 to 10 days, preferably from 1 to 7 days from the treatment of the plants with active products The good compatibility with plants and active products at the concentrations required for the control of plant diseases allows treatment of the aerial parts of plants, seedlings and seeds and of the soil. The active ingredients, according to the invention, can be used with particular success in the control of cereal diseases, such as For example, against types of Puccinia and diseases in the vineyard, fruit and vegetable plantations, such as, for example, against types of Botrytis, Venturia or Alternaria. The active compounds according to the invention are also suitable for increasing the yield of crops. It also has a low toxicity and _ they have good compatibility with plants. The active products, according to the invention, they can be used, if appropriate, in certain concentrations and amounts of application, also as herbicides, to influence the growth of plants, as well as for the control against animal pests. These can also be used, if appropriate, as intermediates and as starting materials for the synthesis of other active products. All plants and parts of plants can be treated according to the invention. By plants, all plants and plant populations, such as desired and unwanted wild plants (including crop plants of natural origin), will be understood in this case. The crop plants can be plants that can be obtained by conventional methods and cultivation and optimization or by means of biotechnological and genetic engineering methods, including transgenic plants and including plant varieties that can be protected or not through the right of protection of plant varieties. By parts of the plants should be understood all parts and aerial and underground organs of plants, such as buds, leaves, flowers and roots, being able to indicate in an exemplary way leaves, needles, stems, trunks, flowers, fruit bodies, fruits and seeds as well as roots, tubers and rhizomes. The harvests as well as vegetative and generative reproductive material, for example seedlings, tubers, rhizomes, layering and seeds, also belong to the parts of the plants. The treatment according to the invention of plants and parts of the plants with the active products is carried out directly or by action on the environment, the biotope or the storage enclosure in accordance with the usual treatment methods, by example by immersion, spraying, evaporation, nebulization, spreading, application by brush and, in the case of the reproduction material, especially in the case of seeds, also by coating with one or more layers. The products according to the invention can be used in the protection of industrial materials against attack and destruction due to undesirable microorganisms. Industrial materials in the present context will be understood as non-living materials, which have been prepared for use in the art. By way of example, the technical materials, which would be protected against microbial modifications or destructions by means of the active products according to the invention, are glues, glues, paper and cardboard, textiles, leather, wood, paints and articles of synthetic material. , cold lubricants and other materials. In the field of the materials to be protected, parts of production facilities may also be mentioned, for example, closed cooling water circuits, which may be adversely affected by the multiplication of the microorganisms. Technical materials preferably adhesives, glues, paper and cardboard, leather, wood, paints, cold lubricants and heat transfer liquids, particularly preferably wood, as micro-organisms, which can cause the decomposition or modification of technical materials, can Bacteria, fungi, yeasts, algae and mucilaginous organisms are mentioned by way of example, The active compounds according to the invention preferably act against fungi, in particular against molds, fungus coloring and destroying wood (Basidiomycetes) as well as against mucilaginous organisms and algae As an example, I can cite Crops of the following types: Alternating, such as Alternaria tenuis, Aspergillus, such as Aspergillus niger, Chaetomium, such as Chaetomium globosum, Coniophora, such as Coniophora puetana, Lentinus, such as Lentinus tigrinus, Penicillium, such as Penicillium glaucu, Polyporus, such as Polyporus versicolor, Aureobasidium, such as Aureobasidium pullulans, Sclerophoma, such as Sclerophoma pityophila, Trichoderma, such as Trichoderma viride, Escherichia, such as Escherichia coli, Pseudomonas, such as Pseudomonas aeruginosa, Staphylococcus, such as Staphylococcus aureus. The active products can be transformed, depending on their respective physical and / or chemical properties, into the customary formulations such as solutions, emulsions, suspensions, powders, foams, pastes, granulates, aerosols, microencapsulated in polymeric materials and in coating compositions. seeds, as well as formulations of cold fogging and hot in ultralow volume (ULV). These formulations are prepared in a known manner, for example by mixing the active ingredients with spreading agents, that is to say liquid solvents, liquefied gases, which are under pressure and / or solid support materials, optionally with the use of surfactants, that is, emulsifiers and / or dispersants and / or foam generating agents. In the case of the use of water as an extender agent, organic solvents can also be used as auxiliary solvents. Suitable liquid solvents are: aromatic hydrocarbons, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatic hydrocarbons or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylene or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum, alcohols, such as butanol or glycol, as well as ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulfoxide as well as water. By liquefied gaseous extenders or support materials are meant those which are gaseous at normal temperature and under normal pressure, for example propellant gases for aerosol, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide. Suitable solid support materials are, for example, natural mineral flours, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite, or diatomaceous earth and synthetic mineral flours, such as highly dispersed silicic acid, aluminum and silicates. Suitable solid support materials for granules are, for example, broken minerals and fractions, such as calcite, pumice, marble, sepiolite, dolomite, as well as synthetic granules formed from inorganic and organic flours and granulates formed from material. organic products such as sawdust, coconut husks, corn ears and tobacco stems. Suitable emulsifying and / or foam generating agents are, for example, nonionic and anionic emulsifiers, such as polyoxyethylenated fatty acid esters, polyoxyethylenated fatty alcohol ethers, for example alkylaryl polyglycolfer, alkylsulfonates, alkyl sulfates, arylsulfonates, and albumin hydrolysates. Suitable dispersants are, for example, sulfite lignin blends and methylcellulose. They can be used in the adhesive formulations such as carboxymethylcellulose, natural and synthetic polymers powdery, granular or in the form of latexes, such as gum arabic, polyvinyl alcohol, polyvinyl acetate as well as natural phospholipids, such as cefaliña and lecithin and synthetic phospholipids. Other additives can be mineral and vegetable oils . Dyes such as inorganic pigments, for example iron oxide, titanium oxide, ferrocyanide blue and organic colorants such as alizarin, azo and metal phthalocyanine dyes and trace nutrients, such as iron, manganese salts, may be employed., boron, copper, cobalt, molybdenum, zinc. The formulations generally contain between 0.1 and 95 weight percent active product, preferably between 0.5 and 90%. The active compounds according to the invention can be present as such or in their formulations also in a mixture of known fungicides, bactericides, acaricides, nematicides or insecticides, in order to extend, for example, the spectrum of activity or the development of the resistance. In many cases, synergistic effects are obtained, ie the activity of the mixture is greater than the activity of the individual components, as the mixing components, for example, the following compounds are considered: Fungicides: 2-phenylphenol; 8-hydroxyquinoline sulfate; Acibenzolar-S-methyl; Aldimorph; Amidoflumet; Ampropylfs; Ampropylfos-potassium; Andoprim; Anilazine; Azaconazole; Azoxystrobin; Benalaxyl; Benalaxyl-M; Benodanil; Benomyl; Benthiavalicarb-isopropyl; Benzamacril; Benzamacril-isobutyl; Bilanafos, Binapacryl; Biphenyl; Bitertanol; Blasticidin-Sj Bromuconazole; Bupirimate; Buthiobate; Butylamine; calcium polysulfide; Capsimycin; Captafol; Captan Carbendazim; Carboxin; Carpropamid; Carvone; Chinomethionat Chlobenthiazone; Chlorfenazole; Chloroneb; Chlorothalonil Chlozolinate; Clozylacon; Cyazofamid; Cyflufenamid Cymoxanil; Cyproconazole; Cyprodinil; Cyprofuram; Dagger G Debacarb; Dichlofluanid; Dichlone; Dichlorophen; Diclocymet Diclomezine; They diclored; Diethofencarb; Difenoconazole Diflumetorim; Dimethirimol; Dimethomorph; Dimoxystrobin Diñiconazole; Diniconazole-M; Dinocap; Diphenylamine Dipyrithione; Ditalimfos; Dithianon; Dodine; Drazoxolon Edifenphos; Epoxiconazole; Ethaboxam; Ethyrimol; Etridia-zole Famoxadone; Fena idone; Fenapanil; Fenarimol; Fenbuconazole Fenfuram; Fenhexamid; Fenitropan; Fenoxanil; Fenpiclonil Fenpropidin; Fenpropimorph; Ferbam; Fluazinam; Flubenzimine Fludioxonil; Flumetover; Flumorph; Fluoromide; Fluoxastrobin Fluquinconazole; Flurprimidol; Flusilazole; Flusulfamide Flutolanil; Flutriafol; Folpet; Fosetyl-Al; Fosetyl-sodium Fuberidazole; Furalaxyl; Furametpyr; Furcarbanil Furmecyclox; Guazatine; hexachlorobenzene; Hexaconazole Hymexazole; Imazalil; Imibenconazole; Iminoctadine triacetate Iminoctadine tris (albesil; Iodocarb; Ipconazole; Iprobenfos Iprodione; Iprovalicarb; Iruvamycin; Isoprothiolane Isovaledione; Kasugamycin; Kresoxim-methyl; Mancozeb; Maneb Meferimzone; Mepanipyrim; Mepronil; Metalaxyl; Metalaxyl-M Metconazole; Methasulfocarb; Methfuroxam; Metiram Metominostrobin; metsulfovax; Mildiomycin; Myclobutanil Myclozolin; Natamycin; nicobifen; nitrothal-isopropyl Noviflumuron; Nuarimol; Ofurace; orysastrobin, oxadixyl oxolinic acid; Oxpoconazole; oxycarboxin; Oxyfenthiin Paclobutrazol; Pefurazoate; penconazole, pencycuron Phosdiphen; Phthalide; picoxystrobin; Piperalin; Polyoxins Polyoxorim; Probenazole; Prochloraz; Procymidone Propamocarb; Propanosine-sodium; Propiconazole; Propineb Proquininazid; Prothioconazole; Pyraclostrobin; Pyrazophos Pyrifenox; Pyrimethanil; Pyroquilon; Pyroxyfur Pyrrolnitrine; Quinconazole; Quinoxyfen; Quintozene Simeconazole; Spiroxamine; Sulfur; Tebuconazole; Tecloftalam Tecnazene; Tetcyclacis; Tetracon; azole; Thiabendazole Thicyofen; Thifluzamide; Thiophanate-methyl; Thira Tioxymid; Tolclofos-methyl; Tolylfluanid; Triadimefon Triadimenol; Triazbutyl; Triazoxide; Tricyclamide Tricyclazole; Tridemorph; Trifloxystrobin; Triflumizole Triforine; Triticonazole; Uniconazole; Validamycin A Vinclozolin; Zineb; Zira; Zoxamide; (2S) -N- [2- [4- [[3- (4-chlorophenyl) -2-propynyl] oxy] -3-methoxyphenyl] ethyl] -3-methyl-2- [(methyl-sulfonyl) amino] -butanoamide; 1- (1-naphthalenyl) -1H-pyrrole-2, 5-dione; 2,3,5,6-tetrachloro-4- (methylsulfonyl) -pyridine; 2-amino-4-methyl-N-phenyl-5-thiazolecarboxamide; 2-chloro-N- (2, 3-dihydro-1,1,3-trimethyl-lH-inden-4-yl) -3-pyridinecarboxamide; 3,4,5-trichloro-2,6-pyridinedicarbonitrile; Actinovate-cis-1- (4-chlorophenyl) -2- (1H-1,2,4-triazol-1-yl) -cycloheptanol; 1- (2,3-dihydro-2, 2-dimethyl-lH-inden-l-yl) -1H-imidazole-5-carboxylic acid methyl; monopotassium carbonate; N- (6-methoxy-3-pyridinyl) -cyclopropanecarboxamide; N-butyl-8- (1,1-dimethylethyl) -1-oxaspiro [.5] decan-3-amine; sodium tetrathiocarbonate; as well as copper salts and copper preparations, such as Bordeaux blends; copper hydroxide; copper naphthenate; Copper oxychloride; copper sulphate; Cufraneb; copper oxide; Mancopper; copper oxine. Bactericides: Bronopol, Dichlorophen, Nitrapyrin, nickel dimethyldithiocarbamate, Kasugamycin, Octhilinon, furancarboxylic acid, Oxytetracyclin, Probenazoly Streptomycin, Tecloftalam, copper sulfate and other copper preparations. Insecticides / acaricides / nematicides: 1. Acetylcholine esterase inhibitors (AChE) 1.1 Carbamates (eg Alanycarb, Aldicarb, Aldoxycarb, Allyxycarb, Aminocarb, Azamethiphos, Bendiocarb, Benfuracarb, Bufencarb, Butacarb, Butocarboxim, Butoxycarboxim, Carbaryl, Carbofuran, Carbosulfan, Chloethocarb , Coumaphos, Cyanofenphos, Cyanophos, Dimetilan, Ethiophencarb, Fenobucarb, Fenothiocarb, Formetanate, Furathiocarb, Isoprocarb, Metam-sodium, Methiocarb, Methomyl, Metolcarb, Oxamyl, Pirimicarb, Promecarb, Propoxur, Thiodicarb, Thiofanox, Triazamate, Trimethacarb, XMC, Xylylcarb) 1.2 Organophosphates (for example Acephate, Azamethiphos, Azinphos ( -methyl, -ethyl), Bromophos-ethyl, Bromfenvinphos (-methyl), Butathiophos, Cadusafos, Carbophenothion, Chlorethoxyphos, Chlorfenvinphos, Chlormephos, Chlorpyrifos (- methyl / -ethyl), Coumaphos, Cyanofenphos, Cyanophos, Chlorfenvinphos, Demeton-S- methyl, Demeton-S-methylsulfone, Dialiphos, Diazinon, Dichlofenthion, Dichlorvos / DDVP, Dicrotophos, Dimethoate, Dimethylvinphos, Dioxabenzofos, Disulfoton, EPN, Ethion, Ethoprophos, Etrimphos, Famphur, Fenamiphos, Fenitrothion, Fensulfothion, Fenthion, Flupyrazophos, Fonofos, Formothion, Fosmethilan, Fosthiazate, Heptenophos, Iodofenphos, Iprobenfos, Isazophos, Isofenphos, Isopropyl O-Salicylate, Isoxathion, Malathion, Mecarbam, Methacrifos, Methamidophos, Methidathion, Mevinp Hos, Monocrotophos, Naled, Omethoate, Oxydemeton-methyl, Parathion (-methyl / -ethyl), Phenthoate, Phorate, Phosalone, Phosmet, Phosphamidon, Phosphocarb, Phoxim, Pirimiphos. { -methyl / -ethyl), Profenofos, Propaphos, Propetamphos, Prothiophos, Prothoate, Pyraclofos, Pyridaphenthion, Pyridathion, Quinalphos, Sebufos, Sulfotep, Sulprofos, Tebupirimfos, Temephos, Terbufos, Tetrachlorvinphos, Thiometon, Triazophos, Trichlorphon, Vamidothion) 2. Modulators sodium channel / sodium channel blockers as a function of tension 2.1 Pyrethroids (eg Acrinathrin, Allethrin (d-cis-trans, d-trans), Beta-Cyfluthrin, Bifenthrin, Bioallethrin, Bioallethrin-S-cyclopentyl-isomer , Bioethanomethrin, Biopermethrin, Bioresmethrin, Chlovaporthrin, Cis-Cypermethrin, Cis-Resmethrin, Cis-Permethrin, Clocythrin, Cycloprothrin, Cyfluthrin, Cyhalothrin, Cypermethrin (alpha-, beta-, theta-, zeta-), Cyphenothrin, DDT, Deltamethrin, Empenthrin (IR isomer), Esfenvalerate, Etofenprox, Fenfluthrin, Fenpropathrin, Fenpyrithrin, Fenvalerate, Flubrocythrinate, Flucythrinate, Flufenprox, Flumethrin, Fluvalinate, Fubfenprox, Gamma-Cyhalothrin, Imiprothrin, Kadethrin, Lambda-Cyhalothrin, Metofluthrin, Permethrin (cis-, trans-), Phenothrin (lR-trans isomer), Prallet rin, Profluthrin, Protrifenbute, Pyresmethrin, Resmethrin, RU 15525, Silafluofen, Tau-Fluvalinate, Tefluthrin, Terallethrin, Tetramethrin (isomer IR), Tralomethrin, Transfluthrin, ZXI 8901, Pyrethrins (pyrethrum)) 2.2 Oxadiazines (for example Indoxacarb) 3. Acetoncholine receptor agonists / -antagonists 3.1 Cloronicotinyl / neonicotinoids (for example Acetamiprid, Clothianidin, Dinotefuran, Imidacloprid, Nitenpyram, Nithiazine, Thiacloprid, Thiamethoxam) 3.2 Nicotine, Bensultap, Cartap 4. Acetylcholine receptor modulators 4.1 Spinosids (eg Spinosad) 5. Chloride channel antagonists controlled by GABA . 1 Cyclodiene organochlorides (for example Camphechlor, Chlordane, Endosulfan, Gamma-HCH, HCH, Heptachlor, Lindane, Methoxychlor 5.2 Fiproles (for example Acetoprole, Ethiprole, Fipronil, Vaniliprole) 6. Activators of the chloride channel ~ 6.1 Mectins (for example Abamectin, - Avermectin, Emamectin, Emamectin-benzoate, Ivermectin, Milbemectin, Milbemycin) 7. Hormone mimetics juvenile (for example - Diofenolan, Epofenonane, Fenoxycarb, Hydroprene, Kinoprene, Methoprene, Pyriproxifen, Triprene) 8. Ecdyson disruptors / agonists 8.1 Diacylhydrazines (for example Chromafenozide, Halofenozide, Methoxyfenozide, Tebufenozide) 9. Chytrine biosynthesis inhibitors 9.1 Benzoylureas (for example Bistrifluron, Chlofluazuron, Diflubenzuron, Fluazuron, Flucycloxuron, Flufenoxuron, Hexaflumuron, Lufenuron, Novaluron, Noviflumuron, Penfluron, Teflubenzuron, Triflumuron) 9.2 Buprofezin 9.3 Cyromazine 10. Inhibitors of oxidative phosphorylation , disruptors of "ATP 10.1 Diafenthiuron 10.2 Organotins (for example Azocyclotin, Cyhexatin, Fenbutatin-oxide) 11. Decouplers of oxidative phosphorylation by interruption of H protonic gradient 11.1 Pyrroles (for example Chlorfenapyr) 11.2 Dinitrophenols (for example Binapacyrl, Dinobuton, 12. Inhibitors of electronic transport on the I side 12.1 METI 's (for example Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad, Tolfenpyrad) 12.2 Hydramethylnone 12.3 Dicofol 13. Inhibitors of electronic transport on side II 13.1 Rotenone 14 Inhibitors of electronic transport on side III 14.1 Acequinocyl, Fluacrypyrim 15. Microbial disruptors of the intestinal membrane of insects strains of Bacillus thuringiensis 16. Inhibitors of the synthesis of fats 16.1 Tetronic acids (for example Spirodiclofen, Spiromesifen) 16.2 tetrahydric acids [for example carbonate of 3- (2, 5- dimethylphenyl) -8-methoxy-2-oxo-l-azaspiro [4.5] dec-3-en-4-yl ethyl (aka: Carbonic acid, 3- (2, 5-dimethylphenyl) -8- methoxy-2 -oxo-l-azaspiro [4.5] dec-3-en-4-yl ethyl ester, CAS- Reg. -No. : 382608-10-8) and Carbonic acid, cis -3- (2,5-dimethylphenyl) -8-methoxy-2-oxo-l-azaspiro [4.5] dec-3-en-4-yl ethyl ester (CAS -Reg. -? O.: 203313-25-1)] 17. Carboxamides (for example Flonicamid) .18. Octopaminergic agonists (for example Amitraz) 19. Magnesium-stimulated ATPase inhibitors (for example Propargite) 20. Phthalamides (for example? 2- [1, l-dimethyl-2- (methylsulfonyl) ethyl] -3-iodo-N1 - [2-methyl-4- [1,2,2, 2-tetrafluoro-1- (trifluoromethyl) ethyl] phenyl] -1,2-benzenedicarboxamide (CAS-Reg. -? O .: 272451-65-7) ) 21. Nereistoxin analogues (eg Thiocyclam hydrogen oxalate, Thiosultap-sodium) 22. Biological products, hormones or pheromones (eg Azadirachtin, Bacillus spec., Beauveria spec., Codlemone, Metarrhizium spec., Paecilomyces spec., Thuringiensin. , Verticillium spec.) 23. Active products with unknown or non-specific actuation mechanisms 23.1 Agents for gasification (eg aluminum phosphide, methyl bromide, sulfuryl fluoride) 23.2 Selective intake inhibitors (eg Cryolite , Flonicamid, Pymetrozine) 23.3 Mite growth inhibitors (for example Clofen tezine, Etoxazole, Hexythiazox) 23.4 Amidoflumet, Benclothiaz, Benzoximate, Bifenazate, Bromopropylate, "Buprofezin, Chinomethionat, Chlordimeform, Chlorobenzilate, Chloropicrin, Clothiazoben,. Cycloprene, Dicyclanil, Fenoxacrim, Fentrifanil, Flubenzimine, Flufenerim, Flutenzin, Gossyplure, Hydramethylnone, Japonilure, Metoxadiazone, Petroleum, Piperonyl butoxide, potassium oleate, Pyridalyl, Pyriprole, Sulfluramid, Tetradifon, Tetrasul, Triarathene, Verbutin, plus the compound 3- methyl-phenyl-propylcarbamate (Tsumacide Z), the compound 3- (5-chloro-3-pyridinyl) -8- (2,2, 2-trifluoroethyl) -8-azabicyclo [3.2.1] oct-an-3- carbonitrile (CAS-Reg .-- No. 185982-80-3) and the corresponding 3-endo-isomer (CAS-Reg .-- No. 185984-60-5) (see publication WO-96/37494, WO-98/25923), as well as preparations, containing plant extracts of insecticidal action, nematodes, fungi or viruses. A mixture with other known active ingredients, such as herbicides or with fertilizers and growth regulators is also possible. In addition, the compounds according to the invention of the formula (I) also have very good antifungal effects. They have a spectrum of very broad antifungal activity, especially against dermatophytes and blastomycetes, molds and against diphasic fungi (for example against Candida species, such as Candida albicans, Candida glabrata) as well as Epider ophyton floccosum, Aspergillus species, such as Aspergillus niger and Aspergillus fumigatus, Trichophyton species, such as Trichophyton mentagrophytes, micro-pod species, such as Microsporon canis and audouinii. The enumeration of these fungi does not represent in any way a limitation of the fungal spectrum to be considered but it has only an orientative character. The active compounds can be used in the form of their formulations or in the application forms prepared therefrom, such as solutions, suspensions, sprayable powders, pastes, soluble powders, powders and granules ready for use. The application is carried out in the usual manner, for example by watering, spraying, dusting, spreading, sprinkling, foaming, brush application, etc. It is also possible to apply the active products according to the ultra-low volume process or to inject the preparation of the active product 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 application amounts can vary within wide limits in accordance with the type of application. When the parts of the plants are treated, the application quantities of active product are, in general, 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 application amounts of the active compound are, in general, between 0.001 and 50 g per kilogram of seeds, preferably between 0.01 and 10 g per kilogram of seeds. In the case of the treatment of the land, the application quantities of active product are, in general, between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g / ha. As already indicated above, all plants and their parts can be treated according to the invention. In a preferred embodiment, plants and plant varieties as well as parts thereof of wild origin or that are obtained by conventional biological cultivation methods, such as crossing or fusion of protoplasts, are treated. In another preferred embodiment, plants and varieties of transgenic plants, which have been obtained according to genetic engineering methods if appropriate in combination with conventional methods (genetically modified organisms) and their parts are treated. The expression "parts" or "parts of plants" or "components of plants" has been previously explained. Particularly preferred are plants, according to the invention, of the plant varieties customary in the market or in use. Plant varieties are understood as plants with new properties ("characteristics"), which have been cultivated either by conventional culture, by mutagenesis or by recombinant DNA techniques. These can be varieties, biotypes or genotypes. In accordance - with the types of plants or the varieties of the plants, their location and the growth conditions (soil, climate, vegetation period, feeding) can also be presented by means of the treatment according to the invention additive effects ("synergistic"). In this way they are possible, for example, lower amounts of application and / or enlargements of the spectrum of activity and / or a reinforcement of the effect of the products employable according to the invention, improve plant growth, greater tolerance to high or low temperatures, higher tolerance against drought or against the salt content of water or soil, greater floral yield, easier harvesting, acceleration of maturation, higher crop yields, higher quality and / or higher nutritional value of the products harvested, greater storage capacity and / or transformation of the products collected, which go beyond the expected effect itself. To plants or varieties of transgenic plants (obtained by genetic engineering) to be treated preferably according to the invention, belong all plants, which have acquired genetic material by modification "by genetic engineering, which provide them." valuable properties plants especially advantageous ("features"). Examples of such properties are a better -growth of the plants, greater tolerance to high or low temperatures, greater tolerance to drought or against the salt content of water or soil, greater floral yield, easier harvesting, acceleration of ripening, higher crop yields, higher quality and / or higher nutritional value of the products harvested, greater storage capacity and / or transformation of the products harvested. Other examples, especially noteworthy for such properties are the greater resistance of plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and / or viruses as well as a greater tolerance of plants against certain active herbicide products. Examples of transgenic plants are the important crop plants, such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, tobacco, rapeseed as well as fruit tree plantations (with the fruits apple, pear, citrus and grape) , especially corn, soybeans, potatoes, cotton, tobacco and rapeseed. As properties ("characteristics") will be pointed out - especially the greater resistance of the plants against. insects, arachnids, nematodes and snails by means of the toxins generated in plants, especially those generated in plants by the genetic material from Bacillus Thuringiensis (for example by means of the Cry? A (a) genes), Cry? A (b), Cry? A (c), CrylIA, CrylIIA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CrylF as well as their combinations), (hereinafter referred to as "Bt plants"). As properties ("characteristics") should be noted, especially, the greater resistance of plants against fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexin, elicitors as well as resistance genes and proteins and corresponding expressed toxins. As properties ("characteristics"), in particular, the greater tolerance of the plants to certain herbicidal active compounds, for example imidazolinones, sulfonylureas, glyphosate or Phosphinotrichin (for example "PAT" gene) must be pointed out. The genes that provide the respective desired properties ("characteristics") may also be present in combinations with each other in the transgenic plants. Examples of "Bt plants" include corn varieties, cotton varieties, soya varieties and potato varieties, which are marketed under the trademarks YIELD GARD® (for example corn, cotton, soybean), KnockOut® (for example corn), StarLink® (for example corn), Bollgard® (cotton), Nucotn® (cotton) and? ewLeaf® (potato). Examples of herbicide tolerant plants include maize varieties, cotton varieties and soya varieties, which are marketed under the trademarks Roundup Ready® (tolerance against Glyphosate, eg corn, cotton, soybean), Liberty Link ® (tolerance against Phosphinothricin, for example rapeseed), IMI® (tolerance against imidazolinones) and STS® (tolerance against sulfonylureas for example maize) As herbicide-resistant plants (conventionally grown in relation to tolerance to herbicides) can be cited also the varieties marketed for the denomination Clearfield® (for example corn) Obviously these manifestations are valid also for the varieties of plants developed in the future or that are marketed or developed in the future with these genetic properties ("characteristics") .
The stated plants can be treated in a particularly advantageous manner according to the invention with the compounds of the general formula (I) or mixtures of the active compounds according to the invention. The preferred sectors, previously mentioned, in the case of active products or mixtures, are also valid for the treatment of these plants. It should be noted in a special way the treatment of the plants with the compounds or with the mixtures indicated especially in the present text. The obtaining and use of the active products according to the invention are apparent from the following examples. Preparation examples E emplo 1 They are added to a solution, consisting of 240 mg (1.2 mmol) of 2- [2- (trimethylsilyl) ethyl] thiophene-3-amine, in 15 ml of acetonitrile, 183 mg (1.3 mmol) of sodium carbonate. potassium and 443 mg (2.1 mmol) of 2-chloronicotinoyl chloride. After 16 hours at room temperature, pour the reaction mixture over water, extract with ethyl acetate, dry over sodium sulfate and concentrate in vacuo. Column chromatography (cyclohexane / ethyl acetate gradient) provides 100 mg (24% theory) of 2-chloro-N-. { 2- [2- (Trimethylsilyl) ethyl] -3-thienyl} nicotinamide [log P (pH 2.3) = 3.65]. In a manner analogous to that of Example 1, and in accordance with the indications given in the general description of the process, the compounds of the formula (I) indicated in Table 1 below are obtained. Table 1 Obtaining the starting materials of the formula (VI) Example (VI-1) 7.8 ml of n-BuLi (1.6 M in hexane, 0.013 mol), under an argon atmosphere, are added dropwise at -78 ° C to a solution consisting of 5.0 g (0.025 moles). ) of N- (3-thienyl) carbamate of tere. -butyl in 50 ml of THF. After 30 minutes at -78 ° C, the reaction mixture is heated to -10 ° C and combined with a solution composed of 7.6 g (0.030 mol) of iodine in 20 ml of THF. After one hour at -10 ° C the reaction mixture is warmed up to room temperature, poured into water, extracted with ethyl acetate, dried overnight and concentrated in vacuo. Column chromatography (cyclohexane / ethyl acetate 10: 1) provides 4.8 g (59% theory) of (2-iodo-thiophen-3-yl) -tere. -butoxy carbamate. ^ -NMR (CD3CN): d = 1.48 (s, 9H), 6.87 (broad s, 1H), 7.22 (d, ÍH), 7.55 (d, 1H) ppm. Obtaining the starting products of the formula (VIII)? employment (VIII-1) Dissolve, under protective gas (argon), 4.8 g (0.015 mol) of (2-iodo-thiophen-3-yl) -tert.-butoxycarbamate (VI-1) in 50 ml of triethylamine and combine with 622 mg (0.89 mmoles) of bis (triphenylphosphine) palladium (II) chloride, with 169 mg (0.89 mmoles) of cuprous iodide (I) and with 2.2 g (0.022 mmoles) of trimethylsilylacetylene_. The reaction mixture is stirred for 14 hours at room temperature then poured into water, extracted with ethyl acetate, dried overnight and concentrated in vacuo. Column chromatography (cyclohexane / ethyl acetate 10: 1) provides 3.7 g (84% of theory) of carbamate de tere. -butil-. { 2- [(trimethylsilyl) ethynyl] -3-thienyl} . ^ -NMR (CDCN): d = 0.06 (s, 9H), 1.31 (s, 9H), 7.08 (s broad, 1H), 7.10 (d, ÍH), 7.30 (d, lH) ppm. Obtaining the starting products of the formula (IX) (CH 3 A reaction mixture consisting of 2.9 g (9.8 mmol) of tert-butyl carbamate is hydrogenated in an autoclave, {2- [(trimethylsilyl) ethynyl] -3-thienyl) (VIII-1) in 50 ml of methanol and 800 mg of palladium (5% on carbon) for 10 hours under 8 bars of hydrogen and, after addition of others 800 mg of palladium (5% on charcoal) for another 10 hours (8 hydrogen bars). The reaction mixture is filtered through silica gel and concentrated in vacuo, which provides 2.8 g (95% of theory) of [2- (2-trimethylsilanyl-ethyl) -thiophene-3-yl. ] -tere. -butoxycarbamate. XH-NMR (CD3CN): d = 0.04 (s, 9H), 0.85-0.90 (m, 2H), 2.64-2.70 (m, 2H), 1.49 (s, 9H), 6.89 (broad s, HI), 7.02-7.06 (m, 2H) ppm. Obtaining the starting materials of the formula (III) Example (III-l) They are added to a solution consisting of 2.8 g (9.3 mmol) of [2- (2-trimethylsilanyl-ethyl) -thiophen-3-yl] -tere. -butoxycarbamate (IX-1), in 50 ml of dichloromethane, 5 ml of trifluoroacetic acid. The reaction solution is stirred for 3 hours at room temperature and then concentrated in vacuo. Column chromatography (gradient cyclohexane / ethyl acetate 4: 1 then 1: 1) gives 1.2 g (65% of theory) of 2- (2-trimethylsilanyl-ethyl) -thiophene-3-ylamine [logP (pH 2.3) = 1.78]. The determination of the logP values was carried out in accordance with EEC Directive 79/831 annex V.A8 by HPLC (high performance liquid chromatography) on a column with phase inversion (C 18). Temperature 432C. Eluents for the determination in the acid range (pH 2.3): 0.1% aqueous phosphoric acid, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile. The calibration was carried out with unbranched alcan-2-ones (with 3 to 16 carbon atoms), whose logP values are known (determination of the logP values by means of the retention times pro linear interpolation between two alkanones successive). The maximum lambda values were determined by means of the UV spectra from 200 nm to 400 nm at the maximums of the chromatography signals. Application examples: Example A Test with Podosphaera (apple tree) / protector Solvent: 24.5 Parts by weight of acetone. 24.5 Parts by weight of dimethylacetamide. Emulsifier: 1 Part by weight of alkyl aryl polyglycol ether.
To obtain a suitable active preparation, 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 sprayed with the preparation of the active compound in the indicated application amount. After drying the coating, applied by spraying, the plants are inoculated with an aqueous suspension of spores of the pathogen of the late blight of the apple tree Podosphaera leucotricha. The plants are then placed in the greenhouse at approximately 23 ° C and with a relative humidity of about 70% .The evaluation is carried out 10 days after 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 has been observed.
Test with Podosphaera (apple tree) / protector Applied quantity of active Product according to the Degree of active product in invention activity in% g / ha Test with Sphaerotheca (cucumber) / protector Solvent: 24.5 Parts by weight of acetone. 24.5 Parts by weight of dimethylacetamide. Emulsifier: 1 Part by weight of alkyl aryl polyglycol ether.
To obtain a suitable active preparation, 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 sprayed with the preparation of the active compound in the indicated application amount. After drying the coating, applied by spraying, the plants are inoculated with an aqueous suspension of spores of the pathogen Sphaerotheca fulginea. The plants are then placed in the greenhouse at approximately 23 ° C and with a relative humidity of about 70%. The evaluation is carried out 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 has been observed.
Table B Test with Sphaerotheca (cucumber) / protector Applied quantity of active Product according to the Degree of active product in invention activity in% g / ha Example C Assay with Venturia (apple tree) / protector Solvent: 24.5 Parts by weight of acetone. 24.5 Parts by weight of dimethylacetamide. Emulsifier: 1 Part by weight of alkyl aryl polyglycol ether. To obtain a suitable active compound preparation, 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. Young cucumber with the preparation of the active product in the indicated application amount.After drying the spray applied coating the plants are inoculated with an aqueous suspension of conidia of the anthracnose of the Venturia ineaqualis apple tree and remain 1 day at approximately 202 C and with a relative air humidity of 100% in an incubation room The plants are then placed in the greenhouse at approximately 21 aC and with a relative humidity of approximately 90% .The evaluation is carried out after 10 days from inoculation, in this case 0% means a degree of activity, which corresponds to the control s, whereas an activity level of 100% means that no attack has been observed. Table C Venturia (apple tree) / protector test Quantity Grade Active product of applied in accordance with the active product activity invention in g / ha in% Example D Test with Botrytis (beans) / protector Solvent: 24.5 Parts by weight of acetone. 24, 5 parts by weight of dimethylacetamide. Emulsifier: 1 Part by weight of alkyl aryl polyglycol ether. To obtain a suitable active compound preparation, 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 sprayed with the preparation of the active compound in the indicated application amount. After drying the coating, applied by spraying, 2 pieces of agar coated with Botrytis cinerea are placed on each leaf. The inoculated plants are placed in a darkened chamber at approximately 20 ° C and with a relative humidity of 100%. The evaluation is carried out 2 days after the inoculation by means of the magnitude of the spots produced by the attack. 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 has been observed. Table D Test with Botrytis (beans) / protector Quantity Degree Active product of applied in accordance with the active product activity invention in g / ha in% EXAMPLE E Assay with Puccinia (wheat) / protector Solvent: 50 parts by weight ~ of N, N-dimethylacetamide. Emulsifier: 1 Part by weight of alkylaryl polyglycol ether. To obtain a suitable active preparation, 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 sprayed with the preparation of the active compound in the indicated application amount. After drying the coating, applied by spraying, the plants are inoculated with a conidial suspension of recondite Puccinia. The plants remain 48 hours at 20 ° C and with a relative humidity of 100%. The plants are then placed in a greenhouse at a temperature of about 20 ° C and with a relative humidity of 80% to favor the development of rust pustules. The evaluation is carried out 10 days after 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 has been observed. Table E Test with Pucinia (wheat) / protector Quantity Grade - Active product applied in accordance with the active proctuct activity invention in g / ha in% E emplo F In vitro assay for the determination of ED50 in microorganisms It is applied in plate cavities for microtitering, by means of a pipette, a methanolic solution of the active product, to be tested, combined with the PS16 emulsifier. Once the solvent has been removed by evaporation, 200 μl of medium formed by potato dextrose are added to each cavity. The medium had previously been combined with an adequate concentration of spores or mycelia of the fungus to be tested. The resulting concentrations of the active product are 0.05, 0.5, 5 and 50 ppm. The resulting concentration of the emulsifier is 300 ppm. The plates are then incubated for 3-5 days on a vibrating device, at a temperature of 20 aC, until sufficient growth is detected in the untreated controls. The evaluation was carried out photometrically with a wavelength of 620 nm. From the measurement data of the various concentrations, the dose of active compound is calculated, which leads to 50% inhibition of fungal growth compared to untreated controls.
(ED50).
Table F In vitro assay for the determination of ED50 in microorganisms Active product of Microorganism Value ED5Qt according to the invention 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 (1)

Claims Having described the invention as above, the content of the following claims is claimed as property: 1. Silylated carboxamides of the formula (I) characterized in that: M means a ring of thiophene, of pyridine, of pyrimidine, of pyridazine or of pyrazine monosubstituted, respectively, by Y1 or means a thiazole ring substituted by Y2, Y1 means hydrogen, fluorine, chlorine, bromine, methyl, iso-propyl, methylthio or trifluoromethyl, Y2 means hydrogen, fluorine, chlorine, bromine, methyl, methylthio or trifluoromethyl, L means a direct bond or means alkylene (alkanediyl), alkenylene (alkenodiyl) or alkynylene (alkynediyl) respectively straight-chain or of branched chain, optionally substituted, R 1 and R 2 represent, independently of each other, hydrogen, alkyl having 1 to 8 carbon atoms, alkoxy with 1 to 8 carbon atoms, alkoxy with 1 to 4 carbon atoms-alkyl with 1 at 4 carbon atoms, alkylthio having 1 to 4 carbon atoms-alkyl having 1 to 4 carbon atoms or halogenoalkyl having 1 to 6 carbon atoms, R3 signifying hydrogen, alkyl having 1 to 8 carbon atoms, alkoxy with 1 to 8 carbon atoms, alkoxy with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms, alkenyl with 2 to 8 carbon atoms, alkynyl with 2 to 8 carbon atoms, haloalkyl with 1 to 6 carbon atoms, haloalkenyl with 2 to 6 carbon atoms, haloalkynyl with 2 to 6 carbon atoms. carbon, cycloalkyl having 3 to 6 carbon atoms, or means substituted phenyl or phenylalkyl, optionally, R means hydrogen, alkyl having 1 to 8 carbon atoms, alkylsulfinyl having 1 to 6 carbon atoms, alkylsulfonyl having 1 to 6 carbon atoms; carbon atoms, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 3 -C 8 -cycloalkyl; halogenalkyl with 1 to 6 carbon atoms, halogenalkylthio with 1 to 4 carbon atoms, halogenalkylsulfinyl with 1 to 4 carbon atoms, halogenalkylsulfonyl with 1 to 4 carbon atoms, halogenalkoxy with 1 to 4 carbon atoms - alkyl with 1 to 4 carbon atoms, halogencycloalkyl with 3 to 8 carbon atoms with, respectively, 1 to 9 fluorine, chlorine and / or bromine atoms; formyl, formyl-C 1 -C 3 -alkyl, (C 1 -C 3 -alkyl) carbonylalkyl with 1 to 3 carbon atoms, (C 1 -C 3 -alkoxy) C 1 -C alkyl-alkyl to 3 carbon atoms; halogen- (C 1 -C 3 -alkyl) carbonyl-C 1 -C 3 -alkyl, halogen- (C 1 -C 3 -alkoxy) C 1 -C 3 -alkyl-alkyl with, respectively, 1 up to 13 fluorine, chlorine and / or bromine atoms; (C 1 -C 8 alkyl) carbonyl, (C 1 -C 8 alkoxy) carbonyl, (C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl) carbonyl, (C 3 -C akalkyl) 8 carbon atoms) carbonyl; (halogenalkyl with 1-6 carbon atoms) carbonyl, (halogenalkoxy with 1 to 6 carbon atoms) carbonyl, (halogen-alkoxy with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms) carbonyl, (halogenocycloalkyl) with 3 to 8 carbon atoms) carbonyl with, respectively, 1 to 9 fluorine, chlorine and / or bromine atoms; or -C (= 0) C (= 0) R4, -CONR5R6 or -CH2? R7R8, R4 means hydrogen, alkyl with 1 to 8 carbon atoms, alkoxy with 1 to 8 carbon atoms, alkoxy with 1 to 4 atoms carbon-alkyl with 1 to 4 carbon atoms, cycloalkyl with 3 to 8 carbon atoms; halogenalkyl with 1 to 6 carbon atoms, halogenalkoxy with 1 to 6 carbon atoms, halogen-alkoxy with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms, halogencycloalkyl with 3 to 8 carbon atoms with, respectively , 1 to 9 fluorine, chlorine and / or bromine atoms, R5 and R6 mean, independently of each other, respectively hydrogen, alkyl with 1 to 8 carbon atoms, alkoxy with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms, cycloalkyl with 3 to 8 carbon atoms; halogenalkyl with 1 to 8 carbon atoms, halogen-alkoxy with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms, halogencycloalkyl with 3 to 8 carbon atoms with, respectively, 1 to 9 fluorine, chlorine atoms and / or of bromine, R5 and R6 also form, together with the nitrogen atom, with which they are bound, a saturated heterocycle, with 5 to 8 ring atoms, optionally substituted one or more times, in the same or in different forms by halogen or by alkyl having 1 to 4 carbon atoms, the heterocycle containing 1 or 2 heteroatoms, which are not contiguous in the series consisting of oxygen, sulfur or NR9, may contain R7 and R8 independently of each other. yes, hydrogen, alkyl with 1 to 8 carbon atoms, cycloalkyl with 3 to 8 carbon atoms; halogenalkyl with 1 to 8 carbon atoms, halogencycloalkyl with 3 to 8 carbon atoms with, respectively, 1 to 9 fluorine, chlorine and / or bromine atoms, R7 and R8 also form, together with the nitrogen atom, which are linked, a saturated heterocycle, with 5 to 8 atoms in the ring, substituted, if necessary, one or more times, in the same or different ways by halogen or by alkyl with 1 to 4 carbon atoms, contain heterocycle 1 or 2 heteroatoms more, non-contiguous of the series consisting of oxygen, sulfur or NR9, R9 means hydrogen or alkyl with 1 to 6 carbon atoms, A means the rest of the formula (Al) Rlu means hydrogen, hydroxy, formyl, cyano, halogen, nitro, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, halogenalkyl with 1 to 4 carbon atoms, halogenalkoxy with 1 to 4 carbon atoms or halogenalkylthio with 1 to 4 carbon atoms with, respectively, 1 to 5 halogen atoms, aminocarbonyl or aminocarbonyl-alkyl with 1 to 4 carbon atoms, R11 means hydrogen, halogen, cyano, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, halogen with 1 to 4 carbon atoms or halogenalkylthio with 1 to 4 atoms carbon with, respectively, 1 to 5 halogen atoms, and R12 means hydrogen, alkyl with 1 to 4 carbon atoms, hydroxy-alkyl with 1 to 4 carbon atoms, alkenyl with 2 to 6 carbon atoms, cycloalkyl with 3 carbon atoms, to 6 carbon atoms, at quiltium with 1 to 4 carbon atoms - alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms - alkyl with 1 to 4 carbon atoms, halogenoalkyl with 1 to 4 carbon atoms, halogenalkylthio with 1 to 4 carbon atoms-C 1 -C 4 -alkyl, C 1 -C 4 haloalkoxy-C 1 -C 4 -alkyl with, respectively, 1 to 5 halogen atoms, or phenyl, ".-. o A means the rest of the formula (A2) R13 and R14 mean, independently of each other, hydrogen, halogen, alkyl with 1 to 4 carbon atoms or halogen with 1 to 4 carbon atoms with 1 to 5 halogen atoms and R15 means halogen, cyano or alkyl with 1 to 4 atoms carbon, or halogenalkyl with 1 to 4 carbon atoms or halogenalkoxy with 1 to 4 carbon atoms with, respectively, 1 to 5 halogen atoms, A means the rest of the formula (A3) R16 and R17 mean, independently of one another, hydrogen, halogen, alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms and R18 means hydrogen, alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, or A means the remainder of the formula (A4) R 19 is hydrogen, halogen, hydroxy, cyano, alkyl having 1 to 6 carbon atoms, halogen with 1 to 4 carbon atoms, halogen with 1 to 4 carbon atoms or halogen with 1 to 4 carbon atoms with, respectively, 1 up to 5 halogen atoms, or A means the rest of the formula (A5) R20 means halogen, hydroxy, cyano, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, halogenoalkyl with 1 to 4 carbon atoms, haloalkylthio with 1 to 4 carbon atoms - carbon or halogenalkoxy with 1 to 4 carbon atoms with, respectively, 1 to 5 halogen atoms and R21 means hydrogen, halogen, cyano, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, halogenalkyl with 1 to 4 carbon atoms, halogenalkoxy with 1 to 4 carbon atoms with, respectively, 1 to 5 halogen atoms, alkylsulfinyl with 1 to 4 carbon atoms or alkylsulfonyl with 1 to 4 atoms of carbon, or A means the rest of the formula (A6) R "means alkyl having 1 to 4 carbon atoms or halogenalkyl having 1 to 4 carbon atoms with 1 to 5 halogen atoms, O A means the remainder of the formula (A7; R23 means alkyl having 1 to 4 carbon atoms or halogenalkyl having 1 to 4 carbon atoms with 1 to 5 halogen atoms, or - ', -A means the remainder of the formula (A8) R24 and R25 mean, independently of each other, hydrogen, halogen, amino, alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms and R26 means hydrogen, alkyl with 1 to 4 atoms carbon or halogen alkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, or A means the remainder of the formula (A9) R27 and R28 denote, independently of one another, hydrogen, halogen, amino, nitro, alkyl having 1 to 4 carbon atoms or halogenalkyl having 1 to 4 carbon atoms with 1 to 5 halogen atoms and R29 means halogen, alkyl having 1 to 4"carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, or A means the remainder of the formula (AlO) R 3a ~ signifies hydrogen, halogen, amino, alkylamino with 1 to 4 carbon atoms, di- (C 1 -C 4) alkyl amino, cyano, alkyl with 1 to 4 carbon atoms or halogenoalkyl with 1 to 4 carbon atoms carbon with 1 to 5 halogen atoms and R31 means halogen, hydroxy, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, haloalkyl with 1 to 4 carbon atoms or halogenalkoxy with 1 to 4 carbon atoms with, respectively, 1 to 5 halogen atoms, or A means the rest of the formula (All) R 32 is hydrogen, halogen, amino, alkylamino with 1 to 4 carbon atoms, di- (C 1 -C 4 -alkyl) amino, cyano, alkyl with 1 to 4 carbon atoms or halogenoalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms and R33 means halogen, alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, or A means e? rest of the formula (A12) R34 means hydrogen or alkyl with 1 to 4 carbon atoms and R35 means halogen, alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, or A means the rest of the formula (A13) R means hydrogen, halogen, alkyl having 1 to 4 carbon atoms or halogenalkyl having 1 to 4 carbon atoms with 1 to 5 halogen atoms, or A means the remainder of the formula (A14) R 37 is halogen, hydroxy, alkyl having 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, halogen with 1 to 4 carbon atoms, halogen alkyl with 1 to 4 carbon atoms or halogenalkoxy with 1 to 4 carbon atoms with, respectively, 1 to 5 halogen atoms, or A means the remainder of the formula (A15) R38 means hydrogen, cyano, alkyl with 1 to 4 carbon atoms, halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, alkoxy with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms, hydroxy -alkyl with 1 to 4 carbon atoms, alkylsulfonyl with 1 to 4 carbon atoms, di (alkyl with 1 to 4 carbon atoms) aminosulfonyl, alkylcarbonyl with 1 to 6 carbon atoms or means substituted phenylsulfonyl or benzoyl respectively, in case given, R39 means hydrogen, halogen, alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, R40 means hydrogen, halogen, cyano, alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, R41 means hydrogen, halogen, alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, or A signi fica the rest of the formula (A16) -. R42 means halogen, alkyl having 1 to 4 carbon atoms or halogenalkyl having 1 to 4 carbon atoms with 1 to 5 halogen atoms, or A means the remainder of the formula (A17) R means alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms with 1 to 5 halogen atoms, R '44 means alkyl with 1 to 4 carbon atoms, Q1 means S (sulfur), O (oxygen ), SO, S02 or CH2, psignifies 0, 1 or 2, where R44 is the same or different, when p means 2. 2.- Silylated carboxamides of the formula (I) according to claim 1, characterized in that: M means one of the following heterocycles -: - M-9 M-10 M-11 M-12 M-13 the link being linked, marked with "*", with the amide, the bond being marked, marked with "#", with the rest Z, Y1 means hydrogen, fluorine, chlorine, methyl, isopropyl, methylthio or trifluoromethyl, Y2 means hydrogen, methyl, methylthio or trifluoromethyl, L means a direct bond or means alkylene with 1 to 6 carbon atoms, alkenylene with 2 to 6 carbon atoms or alkynylene with 2 to 6 carbon atoms of straight-chain or branched chain, optionally substituted by halogen , R1 and R2 mean, independently of each other, alkyl with 1 to 6 carbon atoms, alkoxy with 1 to 6 carbon atoms, alkoxy with 1 to 3 carbon atoms-alkyl with 1 to 3 carbon atoms or alkylthio with 1 to 3 carbon atoms - alkyl having 1 to 3 carbon atoms, R3 means alkyl with 1 to 6 carbon atoms, alkoxy with 1 to 6 carbon atoms, alkoxy with 1 to 3 carbon atoms - alkyl with 1 to 3 carbon atoms carbon, alkylthio with 1 to 3. "carbon-alkyl atoms with 1 to 3 carbon atoms, cycloalkyl- with 3 to 6 carbon atoms, phenyl or benzyl, R stands for hydrogen, alkyl with 1 to 6 carbon atoms, alkylsulfinyl with 1 to 4 carbon atoms, alkylsulfonyl with 1 to 4 carbon atoms, alkoxy with 1 to 3 carbon atoms - alkyl with 1 to 3 carbon atoms, cycloalkyl with 3 to 6 carbon atoms; haloalkyl with 1 to 4 carbon atoms, halogenalkylthio with 1 to 4 carbon atoms, halogenalkylsulfinyl with 1 to 4 carbon atoms, halogenalkylsulfonyl with 1 to 4 carbon atoms, halogenalkoxy with 1 to 3 carbon atoms-alkyl with 1 to 3 carbon atoms, halogencycloalkyl with 3 to 8 carbon atoms with, respectively 1 to 9, fluorine, chlorine and / or bromine atoms; formyl, formyl-C 1 -C 3 -alkyl, (C 1 -C 3 -alkyl) carbonyl-C 1 -C 3 -alkyl, (C 1 -C 3 -alkoxy) Caryl-alkyl with 1 a 3 carbon atoms; halogen- (C 1 -C 3 -alkyl) carbonyl-C 1 -C 3 -alkyl, halogen- (C 1 -C 3 -alkoxy) C 1 -C 3 -alkyl with, respectively , 1 to 13 fluorine, chlorine and / or bromine atoms; (C 1-6 -alkyl) carbonyl, ("C 1-4 -alkoxy") carbonyl, (C 1-3 -alkoxy-C 1-3 -alkyl) carbonyl, (cycloalkyl) 3 to 6 carbon atoms) carbonyl; (halogenalkyl with 1 to 4 carbon atoms) carbonyl, (halogenalkoxy with 1 to 4 carbon atoms) carbonyl, (halogen-alkoxy with 1 to 3 carbon atoms-alkyl with 1 to 3 carbon atoms) carbonyl, (halogenocycloalkyl with 3 to 6 carbon atoms) carbonyl with, respectively, 1 to 9 fluorine, chlorine and / or bromine atoms; or -C (= 0) C (= 0) R4, -CONR5R6 or -CH2NR7R8, R4 means hydrogen, alkyl having 1 to 6 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkoxy with 1 to 3 carbon atoms -alkyl with 1 to 3 carbon atoms, cycloalkyl with 3 to 6 carbon atoms; halogenalkyl with 1 to 4 carbon atoms, halogenalkoxy with 1 to 4 carbon atoms or, halogen-alkoxy with 1 to 3 carbon atoms-alkyl with 1 to 3 carbon atoms, halogencycloalkyl with 3 to 6 carbon atoms with, respectively , 1 to 9 fluorine, chlorine and / or bromine atoms, R5 and R6 mean, respectively, independently of one another, hydrogen, alkyl having 1 to 6 carbon atoms, alkoxy with 1 to 3 carbon atoms-alkyl with 1 to 3 carbon atoms, cycloalkyl with 3 to 6 carbon atoms; halogenalkyl with 1 to 4 carbon atoms, halogen-alkoxy with 1 to 3 carbon atoms-alkyl with 1 to 3 carbon atoms, halogencycloalkyl with 3 to 6 carbon atoms with, respectively, 1 to 9 fluorine, chlorine atoms and / or bromine, R5 and R6 also form, together with the nitrogen atom, with which they are bound, a saturated heterocycle with 5 or 6 ring atoms, optionally substituted one to four times, same or in different forms by halogen or by alkyl having 1 to 4 carbon atoms, the heterocycle containing 1 or 2 heteroatoms, which may be noncontiguous, may contain the oxygen, sulfur or NR9 series, R7 and R8 mean, independently of each other , hydrogen, alkyl having 1 to 6 carbon atoms, cycloalkyl with 3 to 6 carbon atoms; halogenalkyl with 1 to 4 carbon atoms, halogencycloalkyl with 3 to 6 carbon atoms with, respectively, 1 to 9 fluorine, chlorine and / or bromine atoms, R7 and R8 also form, together with the nitrogen atom, with which they are linked, a saturated heterocycle with 5 or 6 atoms in the ring, optionally substituted one to four times, in the same or different ways by halogen or by alkyl with 1 to 4 carbon atoms, and may contain the heterocycle 1 or 2 heteroatoms more, not contiguous, of the series formed by oxygen, sulfur or NR9, R9 means hydrogen or alkyl with 1 to 4 carbon atoms, A means the residue of the formula (Al) R10 means hydrogen, hydroxy, formyl, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, iso-propyl, methoxy, ethoxy, methylthio, ethylthio, cyclopropyl, halogenalkyl with 1 to 2 carbon atoms, haloalkoxy with 1 to 2. carbon atoms with, respectively, 1 to 5 fluorine, chlorine and / or bromine atoms, trifluoromethylthio, difluoromethylthio, aminocarbonyl, aminocarbonylmethyl or aminocarbonylethyl, R11 means hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, halogenalkyl with 1 to 2 carbon atoms, with 1 to 5 carbon atoms. fluorine, chlorine and / or bromine, and R12 means hydrogen, methyl, ethyl, n-propyl, isopropyl, halogenalkyl with 1 to 2 carbon atoms, with 1 to 5 fluorine, chlorine and / or bromine atoms, hydroxymethyl, hydroxyethyl, cyclopropyl, cyclopentyl, cyclohexyl or phenyl, or A means the remainder of the formula (A2) R13 and R14 mean, independently of each other, hydrogen, fluorine, chlorine, bromine, methyl, ethyl or halogenoalkyl having 1 to 2 carbon atoms, with 1 to 5 fluorine, chlorine and / or bromine atoms and R15 means fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, halogenalkyl with 1 to 2 carbon atoms or halogenalkoxy with 1 to 2 carbon atoms with, respectively, 1 to 5 fluorine, chlorine and / or bromine atoms , or A means the rest of the formula (A3) R and R signify, independently of each other, hydrogen, fluorine, chlorine, bromine, methyl, ethyl or halogenoalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms and R18 means hydrogen, methyl , ethyl or halogenoalkyl with 1 to 2 carbon atoms, with 1 to 5 fluorine, chlorine and / or bromine atoms, or A means the remainder of the formula (A4) R19 means hydrogen, fluorine, chlorine, bromine, iodine, hydroxy, cyano, alkyl with 1 to 4 carbon atoms, halogen with 1 to 2 carbon atoms, halogen with 1 to 2 carbon atoms or halogenalkylthio with 1 to 2 carbon atoms carbon with, respectively, 1 to 5 fluorine, chlorine and / or bromine atoms, or A means the remainder of the formula (A5) R20 means fluorine, chlorine, bromine, iodine, hydroxy, cyano, alkyl having 1 to 4 carbon atoms, methoxy, ethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, halogenalkyl with 1 to 2 carbon atoms or halogenalkoxy with 1 to 2 atoms carbon having, respectively, 1 to 5 fluorine, chlorine and / or bromine atoms and R21 means hydrogen, fluorine, chlorine, bromine, iodine, cyano, alkyl having 1 to 4 carbon atoms, methoxy, ethoxy, methylthio, ethylthio, halogenalkyl with 1 to 2 carbon atoms or halogenalkoxy with 1 to 2 carbon atoms with, respectively, 1 to 5 fluorine, chlorine and / or bromine atoms, alkylsulfinyl with 1 to 2 carbon atoms or alkylsulfonyl with 1 to 2 carbon atoms, or A means the rest of the formula (A8) R24 and R25 mean, independently of each other, hydrogen, fluorine, chlorine, bromine, amino, methyl, ethyl or halogenalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms and R26 means hydrogen , fluorine, chlorine, bromine, iodine, methyl, ethyl or halogenoalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms, or A means the remainder of formula (A9) R27 and R28 denote, independently of one another, hydrogen, fluorine, chlorine, bromine, amino, nitro, methyl, ethyl or halogenoalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms and R29 means fluorine , chlorine, bromine, methyl, ethyl or halogenalkyl having 1 to 2 carbon atoms with 1 to 5 fluorine, chlorine and / or bromine atoms, or A means the remainder of the formula (AlO) R 30 is hydrogen, fluorine, chlorine, bromine, amino, alkylamino with 1 to 4 carbon atoms, di (C 1-4 -alkyl) amino, cyano, methyl, ethyl or haloalkyl with 1 to 2 carbon atoms with 1 up to 5 fluorine, chlorine and / or bromine atoms and R31 means fluorine, chlorine, bromine, hydroxy, methyl, ethyl, methoxy, ethoxy, cyclopropyl, halogenalkyl with 1 to 2 carbon atoms or halogenalkoxy with 1 to 2 carbon atoms carbon with 1 to 5 fluorine, chlorine and / or bromine atoms, A means the rest of the formula (All) R32 means hydrogen, fluorine, chlorine, bromine, amino, alkylamino with 1 to 4 carbon atoms, di (alkyl with 1 to 4 carbon atoms) amino, cyano, methyl, ethyl or haloalkyl with 1 to 2 carbon atoms, with 1 to 5 fluorine, chlorine and / or bromine atoms and R33 means fluorine, chlorine, bromine, methyl, ethyl or halogenalkyl with 1 to 2 carbon atoms, with 1 to 5 fluorine, chlorine and / or of bromine, or A means the rest of the formula (A12) R34 means hydrogen, methyl or ethyl and R35 means fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl or difluoromethyl, or A means the rest of the formula (A13) (A13), wherein R36 means hydrogen, fluorine, chlorine, bromine, methyl, ethyl or halogenoalkyl having 1 to 2 carbon atoms, with 1 to 5 fluorine, chlorine and / or bromine atoms, or A means rest of the formula (A14) R37 means fluorine, chlorine, bromine, iodine, hydroxy, alkyl having 1 to 4 carbon atoms, methoxy, ethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, halogenalkyl with 1 to 2 carbon atoms or halogenalkoxy with 1 to 2 carbon atoms with, respectively, 1 to 5"fluorine, chlorine and / or bromine atoms, or A means the remainder of the formula (A15) R38 means hydrogen, methyl, ethyl, halogenalkyl having 1 to 2 carbon atoms, with 1 to 5 fluorine, chlorine and / or bromine atoms, alkoxy with 1 to 2 carbon atoms-alkyl having 1 to 2 carbon atoms , hydroxymethyl, hydroxyethyl, methylsulfonyl or dimethylaminosulfonyl, R39 means hydrogen, fluorine, chlorine, bromine, methyl, ethyl or halogenalkyl with 1 to 2 carbon atoms, with 1 to 5 fluorine, chlorine and / or bromine atoms, R40 means hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, iso-propyl or halogenalkyl with 1 to 2 carbon atoms, with 1 to 5 fluorine, chlorine and / or bromine atoms, R41 means hydrogen, fluorine , chlorine, bromine, methyl, ethyl or halogenalkyl having 1 to 2 carbon atoms, with 1 to 5 fluorine, chlorine and / or bromine atoms, or A represents the remainder of the formula (A17) R43 means methyl, ethyl or halogenoalkyl having 1 to 2 carbon atoms, with 1 to 5 fluorine, chlorine and / or bromine atoms, R44 means methyl or ethyl, Q1 means S (sulfur), S02 or CH2, psignifies 0 or 1. 3. Process for obtaining the compounds of the formula (I) according to claim 1, characterized in that: a) carboxylic acid derivatives of the formula (II) are reacted wherein A has the meanings indicated in claim 1 Y X1 means halogen or hydroxy, with an amine of the formula (III) wherein M, L, R1, R2, R3 and R have the meanings indicated in claim 1, optionally in the presence of a catalyst, optionally in the presence of a condensing agent, optionally in the presence of a Acid-accepting agent and, if appropriate, in the presence of a diluent, or b) silylated carboxamides of the formula (Ia) are reacted wherein M, L, A, R1, R2 and R3 have the meanings indicated in claim 1 with halides of the formula (IV) RA-X2 (IV) in which X2 means chlorine, bromine or iodine, RA means alkyl with 1 to 8 carbon atoms, alkylsulfinyl with 1 to 6 carbon atoms, alkylsulfonyl with 1 to 6 carbon atoms, alkoxy with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms, cycloalkyl with 3 to 8. -carbon atoms; halogenalkyl with 1 to 6 carbon atoms, halogenalkylthio with 1 to 4 carbon atoms, halogenalkylsulfinyl with 1 to 4 carbon atoms, halogenalkylsulfonyl with 4 carbon atoms, halogenalkoxy with 1 to 4 carbon atoms - alkyl with 1 to 4 carbon atoms, halogencycloalkyl with 3 to 8 carbon atoms with, respectively, 1 to 9 fluorine, chlorine and / or bromine atoms, formyl, formyl-alkyl having 1 to 3 carbon atoms, (alkyl having 1 to 3 carbon atoms) carbonyl-alkyl with 1 to 3 carbon atoms, (alkoxy with 1 to 3 carbon atoms) carbonyl-alkyl with 1 to 3 carbon atoms; halogen- (alkyl with 1 to 3 carbon atoms) carbonyl -alkyl with 1 to 3 carbon atoms, halogen- (alkoxy with 1 to 3 carbon atoms) carbonyl-alkyl with 1 to 3 carbon atoms with, respectively, 1 to 13 fluorine, chlorine and / or bromine atoms (alkyl with 1 to 8 carbon atoms) carbonyl, (alkoxy with 1 to 8 carbon atoms) bonyl, (C 1 -C 4 -alkoxy with 1 to 4 carbon atoms) carbonyl, (cycloalkyl with 3 to 8 carbon atoms) carbonyl; (halogenalkyl with 1 to 6 carbon atoms) carbonyl, (halogenalkoxy with 1 to 6 carbon atoms) carbonyl, (halogen-alkoxy with 1 to 4 carbon atoms-alkyl with 1 to 4 carbon atoms) carbonyl, (halogen-cycloalkyl with 3 to 8 carbon atoms) carbonyl with, respectively, 1 to 9 fluorine, chlorine and / or bromine atoms; or -C (= 0) C (= 0) R4, -CONR5R6 or -CH2NR7R8, where R4, R5, R6, R7 and R8 have the meanings indicated above, in the presence of a base and in the presence of a diluent. 4. - Agents for the fight against undesirable microorganisms, characterized in that they have a content of at least one silylated carboxamide of the formula (I), according to claim 1, together with spreading agents and / or surfactant products. 5. Use of silylated carboxamides of the formula (I) according to claim 1, wherein they are for the control against undesirable microorganisms. 6. Procedure for the fight against undesirable microorganisms, characterized in that silylated carboxamides of the formula (I) are applied, according to claim 1, on the microorganisms and / or on their environment. 7. Process for obtaining agents for combating undesirable microorganisms, characterized in that silylated carboxamides of the formula (I) are mixed according to claim 1 with spreader agents and / or surfactant products. 8.- Amines of the formula (III) characterized by M, L, R1, R2, R3 and R 'have the meanings indicated in accordance with claim
1.
MXPA/A/2006/010344A 2004-03-17 2006-09-11 Silylated carboxamides MXPA06010344A (en)

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