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Title:
HETEROCYCLIC COMPOUNDS FOR THE CONTROL OF UNWANTED MICROORGANISMS
Document Type and Number:
WIPO Patent Application WO/2015/144652
Kind Code:
A2
Abstract:
The present application relates to the use of heterocyclic compounds according to formula (I) for controlling harmful microorganisms in plants, compositions comprising these compounds and to processes for preparation these fungicidal compositions.

Inventors:
DÉCOR ANNE (DE)
HEILMANN EIKE KEVIN (DE)
GREUL JÖRG (DE)
DAHMEN PETER (DE)
WACHENDORFF-NEUMANN ULRIKE (DE)
TRAUTWEIN AXEL (DE)
COQUERON PIERRE-YVES (FR)
RINOLFI PHILIPPE (FR)
BRUNET STÉPHANE (DE)
Application Number:
EP2015/056174
Publication Date:
October 01, 2015
Filing Date:
March 24, 2015
Export Citation:
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Assignee:
BAYER CROPSCIENCE AG (DE)
International Classes:
A01P3/00
Attorney, Agent or Firm:
KOOPMANN, E. (Alfred-Nobel-Str. 10, Monheim am Rhein, DE)
Download PDF:
Claims:
Claims

1. Use of compounds of the formula (I)

in which A represents a radical from the group consisting of

in which the broken line represents the bond to Q and in which A furthermore carries m substituents R2,

Q represents a radical from the group consisting of

in which the nitrogen is attached to ring A and the arrow in each case represents the bond to D and

D represents the radical of the formula

in which the nitrogen is attached to Q and the arrow represents the bond to B,

B represents a radical from the group consisting of

in which the broken line represents the bond to D and in which B furthermore carries n substituents R7,

Y represents CR8 or represents nitrogen,

Z represents oxygen or sulphur,

Rl represents a radical from the group consisting of halogen, cyano, nitro, amino, hydroxy, represents C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C3-C6- alkenyloxy, C3-C6-alkynyloxy, C3-C6-cycloalkyloxy, C1-C6-alkylcarbonyloxy, C2-C6- alkenylcarbonyloxy, C2-C6-alkynylcarbonyloxy, C3-C6-cycloalkylcarbonyloxy, C1-C6- alkoxycarbonyloxy, C1-C6-alkylsulphonyloxy, C1-C6-alkylamino, C3-C6-alkenylamino, C3-C6- alkynylamino, C3-C6-cycloalkylamino, C1-C6-alkylcarbonylamino, C2-C6-alkenylcarbonylamino, C2-C6-alkynylcarbonylamino, C3-C6-cycloalkylcarbonylamino, C1-C6-alkoxycarbonylamino, C1- C6-alkylsulphonylamino, C1-C6-alkylthio, C3-C6-alkenylthio, C3-C6-alkynylthio, C3-C6- cycloalkylthio, C1-C6-alkylsulphinyl, C1-C6-alkylsulphonyl, C1-C6-alkylcarbonyl, C1-C6- alkoxyimino-C1-C6-alkyl, C1-C6-alkoxycarbonyl, aminocarbonyl, C1-C6-alkylaminocarbonyl, di- (C1-C6-alkyl)-aminocarbonyl, aminothiocarbonyl, C1-C6-alkylaminosulphonyl, C1-C6- alkylsulphonylamino, C1-C6-alkylcarbonylamino, C1-C6-alkylthiocarbonylamino, C4-C12- bicycloalkyl, aryl, aryloxy, arylamino, arylthio, heteroaryl, heteroaryloxy, heteroarylamino and heteroarylthio, each of which is optionally substituted by one or more identical or different substituents, where the substituents independently of one another are selected from the group consisting of halogen, cyano, nitro, hydroxy, amino, C1-C6-alkyl, C1-C6-alkoxy, C3-C6- cycloalkyl, C1-C6-haloalkoxy, C1-C6-alkylthio, aryl, aryloxy, arylthio, heteroaryl, heteroaryloxy and heteroarylthio, R2 represents a radical from the group consisting of halogen, cyano, nitro, amino, hydroxy, represents C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C3-C6- alkenoxy, C3-C6-alkynoxy, C3-C6-cycloalkoxy, C1-C6-alkylcarbonyloxy, C2-C6- alkenylcarbonyloxy, C2-C6-alkynylcarbonyloxy, C3-C6-cycloalkylcarbonyloxy, C1-C6- alkoxycarbonyloxy, C1-C6-alkylsulphonyloxy, C1-C6-alkylamino, di-(C1-C6-alkyl)-amino, C1- C6-alkenylamino, C3-C6-alkynylamino, C3-C6-cycloalkylamino, C1-C6-alkylcarbonylamino, C2- C6-alkenylcarbonylamino, C2-C6-alkynylcarbonylamino, C3-C6-cycloalkylcarbonylamino, C1- C6-alkoxycarbonylamino, C1-C6-alkylsulphonylamino, C1-C6-alkylthio, C3-C6-alkenylthio, C3- C6-alkynylthio, C3-C6-cycloalkylthio, C1-C6-alkylsulphinyl, C1-C6-alkylsulphonyl, C1-C6- alkylcarbonyl, C1-C6-alkoxyimino-C1-C6-alkyl, C1-C6-alkoxycarbonyl, aminocarbonyl, C1-C6- alkylaminocarbonyl, di-(C1-C6-alkyl)-aminocarbonyl, aminothiocarbonyl, C1-C6- alkylaminosulphonyl, C1-C6-alkylsulphonylamino, C1-C6-alkylcarbonylamino, C1-C6- alkylthiocarbonylamino, C4-C12-bicycloalkyl, aryl, aryloxy, arylamino, arylthio, heteroaryl, heteroaryloxy, heteroarylamino and heteroarylthio, each of which is optionally substituted by one or more identical or different substituents, where the substituents independently of one another are selected from the group consisting of halogen, cyano, nitro, hydroxy, amino, C1-C6- alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, C1-C6-haloalkoxy and C1-C6-alkylthio, aryl, aryloxy, arylthio, heteroaryl, heteroaryloxy and heteroarylthio, R3 represents a radical from the group consisting of hydrogen, halogen, cyano, nitro, amino, hydroxy, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-haloalkyl and C1-C6-haloalkoxy,

R4 represents a radical from the group consisting of hydrogen, halogen, amino, hydroxy, C1-C6- alkyl, C1-C6-alkoxy, C1-C6-haloalkyl and C1-C6-haloalkoxy,

R5 represents a radical from the group consisting of hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C1- C6-haloalkyl, C2-C6-alkenyl, C3-C6-alkynyl, C3-C6-cycloalkyl-C1-C6-alkyl, cyano-C1-C6-alkyl, C1-C6-alkylcarbonyl, C2-C6-alkenylcarbonyl, C1-C6-haloalkylcarbonyl, C2-C6- haloalkenylcarbonyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxycarbonyl, C1-C6-alkylsulphonyl and C1-C6-haloalkylsulphonyl or represents C(=O)-B, R6 represents a radical from the group consisting of hydrogen (only in the radicals B-26, B-33, B- 36 and B-42), halogen, cyano, nitro, amino, hydroxy, carboxyl, represents C1-C6-alkyl, C2-C6- alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C3-C6-alkenoxy, C3-C6-alkynoxy, C3- C6-cycloalkoxy, C1-C6-alkylcarbonyloxy, C2-C6-alkenylcarbonyloxy, C2-C6- alkynylcarbonyloxy, C3-C6-cycloalkylcarbonyloxy, C1-C6-alkoxycarbonyloxy, C1-C6- alkylsulphonyloxy, C1-C6-alkylcarbonylamino, C2-C6-alkenylcarbonylamino, C2-C6- alkynylcarbonylamino, C3-C6-cycloalkylcarbonylamino, C1-C6-alkoxycarbonylamino, C1-C6- alkylsulphonylamino, C1-C6-alkylthio, C1-C6-alkylsulphinyl, C1-C6-alkylsulphonyl, C1-C6- alkylcarbonyl, C1-C6-alkoxyimino-C1-C6-alkyl, C1-C6-alkoxycarbonyl, aminocarbonyl, C1-C6- alkylaminocarbonyl, di-(C1-C6-alkyl)-aminocarbonyl, aminothiocarbonyl, C1-C6- alkylaminosulphonyl, C1-C6-alkylsulphonylamino, C1-C6-alkylcarbonylamino, C1-C6- haloalkylcarbonylamino, C1-C6-alkylthiocarbonylamino, C4-C12-bicycloalkyl, aryl, aryloxy, heteroaryl, heteroaryloxy, each of which is optionally substituted by one or more identical or different substituents, where the substituents independently of one another are selected from the group consisting of halogen, cyano, nitro, hydroxy, amino, C1-C6-alkyl, C1-C6-alkoxy, C3-C6- cycloalkyl, C1-C6-haloalkoxy and C1-C6-alkylthio, R7 represents a radical from the group consisting of halogen, nitro, cyano, amino, hydroxy, represents C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C3-C6- alkenoxy, C3-C6-alkynoxy, C3-C6-cycloalkoxy, C1-C6-alkylcarbonyloxy, C2-C6- alkenylcarbonyloxy, C2-C6-alkynylcarbonyloxy, C3-C6-cycloalkylcarbonyloxy, C1-C6- alkoxycarbonyloxy, C1-C6-alkylsulphonyloxy, C1-C6-alkylcarbonylamino, C2-C6- alkenylcarbonylamino, C2-C6-alkynylcarbonylamino, C3-C6-cycloalkylcarbonylamino, C1-C6- alkoxycarbonylamino, C1-C6-alkylsulphonylamino, C1-C6-alkylthio, C1-C6-alkylsulphinyl, C1- C6-alkylsulphonyl, C1-C6-alkylcarbonyl, C1-C6-alkoxyimino-C1-C6-alkyl, C1-C6-alkoxycarbonyl, aminocarbonyl, C1-C6-alkylaminocarbonyl, di-(C1-C6-alkyl)-aminocarbonyl, aminothiocarbonyl, C1-C6-alkylaminosulphonyl, C1-C6-alkylsulphonylamino, C1-C6-alkylcarbonylamino, C1-C6- alkylthiocarbonylamino, aryl, aryloxy, heteroaryl, heteroaryloxy, C4-C12-bicycloalkyl, each of which is optionally substituted by one or more identical or different substituents, where the substituents independently of one another are selected from the group consisting of halogen, cyano, nitro, hydroxy, amino, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, C1-C6-haloalkoxy and C1-C6-alkylthio, R8 represents a radical from the group consisting of hydrogen, halogen, amino, hydroxy, C1-C6- alkyl, C1-C6-alkoxy, C1-C6-haloalkyl and C1-C6-haloalkoxy, R9 represents a radical from the group consisting of hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, haloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C3-C6-cycloalkyl-C1-C6-alkyl, cyano-C1-C6-alkyl, C1- C6-alkylcarbonyl, C2-C6-alkenylcarbonyl, C1-C6-haloalkylcarbonyl, C2-C6-haloalkenylcarbonyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxycarbonyl, C1-C6-alkylsulphonyl and C1-C6- haloalkylsulphonyl, m represents a number from the group consisting of 0, 1 , 2 and 3, where for m > 1 the radicals R2 may be identical or different and n represents a number from the group consisting of 0, 1 , 2 and 3, where for n > 1 the radicals R7 may be identical or different, for controlling harmful microorganisms.

2. Use of compounds of the formula (I) according to Claim 1 in which

A represents a radical from the group consisting of

in which the broken line represents the bond to Q and where A furthermore carries m substituents R2,

Q represents a radical from the group consisting of

in which the nitrogen is attached to ring A and the arrow in each case represents the bond to D, D represents the radical of the formula

in which the nitrogen is attached to Q and the arrow represents the bond to B,

B represents a radical from the group consisting of

in which the broken line represents the bond to D and in which B furthermore carries n substituents R7, Y represents CR8 or represents nitrogen, 5 Z represents oxygen or sulphur, R1 represents a radical from the group consisting of halogen, cyano, nitro, amino, hydroxy, C1-C6- alkyl, C1-C6-haloalkyl, cyano-C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3- C6-cycloalkyl-C1-C6-alkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C6-alkenyloxy, C3-C6- alkynyloxy, C3-C6-cycloalkyloxy, C1-C6-alkylcarbonyloxy, C2-C6-alkenylcarbonyloxy, C2-C6-10 alkynylcarbonyloxy, C3-C6-cycloalkylcarbonyloxy, C1-C6-alkoxycarbonyloxy, C1-C6- alkylsulphonyloxy, C1-C6-alkylamino, C3-C6-alkenylamino, C3-C6-alkynylamino, C3-C6- cycloalkylamino, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C6-alkenylthio, C3-C6-alkynylthio, C3-C6-cycloalkylthio, C1-C6-alkylsulphinyl, C1-C6-alkylsulphonyl, C1-C6-alkylcarbonyl, C1-C6- alkoxyimino-C1-C6-alkyl, C1-C6-alkoxycarbonyl, aminocarbonyl, C1-C6-alkylaminocarbonyl, di- (C1-C6-alkyl)-aminocarbonyl, aminothiocarbonyl, C1-C6-alkylaminosulphonyl, C1-C6- alkylsulphonylamino, C1-C6-alkylcarbonylamino, C1-C6-alkylthiocarbonylamino, aryl, aryloxy, heteroaryl and heteroaryloxy, R2 represents a radical from the group consisting of halogen, cyano, nitro, amino, hydroxy, C1-C6- alkyl, C1-C6-haloalkyl, cyano-C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3- C6-cycloalkyl-C1-C6-alkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C6-alkenyloxy, C3-C6- alkynyloxy, C3-C6-cycloalkyloxy, C1-C6-alkylcarbonyloxy, C2-C6-alkenylcarbonyloxy, C2-C6- alkynylcarbonyloxy, C3-C6-cycloalkylcarbonyloxy, C1-C6-alkoxycarbonyloxy, C1-C6- alkylsulphonyloxy, C1-C6-alkylamino, di-(C1-C6-alkyl)-amino, C3-C6-alkenylamino, C3-C6- alkynylamino, C3-C6-cycloalkylamino, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C6-alkenylthio, C3-C6-alkynylthio, C3-C6-cycloalkylthio, C1-C6-alkylsulphinyl, C1-C6-alkylsulphonyl, C1-C6- alkylcarbonyl, C1-C6-alkoxyimino-C1-C6-alkyl, C1-C6-alkoxycarbonyl, aminocarbonyl, C1-C6- alkylaminocarbonyl, di-(C1-C6-alkyl)-aminocarbonyl, aminothiocarbonyl, C1-C6- alkylaminosulphonyl, C1-C6-alkylsulphonylamino, C1-C6-alkylcarbonylamino, C1-C6- alkylthiocarbonylamino, aryl, aryloxy, heteroaryl and heteroaryloxy, R3 represents a radical from the group consisting of hydrogen, halogen, cyano, nitro, amino, C1-C6- alkyl and C1-C6-haloalkyl, R4 represents a radical from the group consisting of hydrogen, halogen, amino, hydroxy, C1-C6- alkyl, C1-C6-alkoxy, C1-C6-haloalkyl and C1-C6-haloalkoxy, R5 represents a radical from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, cyano- C1-C6-alkyl, C2-C6-alkenyl, C3-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, C1- C6-alkylcarbonyl, C2-C6-alkenylcarbonyl, C1-C6-haloalkylcarbonyl, C2-C6-haloalkenylcarbonyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxycarbonyl, C1-C6-alkylsulphonyl, C1-C6- haloalkylsulphonyl and C(=O)-B, R6 represents a radical from the group consisting of hydrogen (only in the radicals B-26, B-33, B- 36 and B-42), halogen, cyano, nitro, amino, hydroxy, carboxyl, C1-C6-alkyl, C1-C6-haloalkyl, cyano-C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C6- alkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6- cycloalkyloxy, C1-C6-alkylcarbonyloxy, C2-C6-alkenylcarbonyloxy, C2-C6-alkynylcarbonyloxy, C3-C6-cycloalkylcarbonyloxy, C1-C6-alkoxycarbonyloxy, C1-C6-alkylsulphonyloxy, C1-C6- alkylamino, C3-C6-alkenylamino, C3-C6-alkynylamino, C3-C6-cycloalkylamino, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C6-alkenylthio, C3-C6-alkynylthio, C3-C6-cycloalkylthio, C1-C6- alkylsulphinyl, C1-C6-alkylsulphonyl, C1-C6-alkylcarbonyl, C1-C6-alkoxyimino-C1-C6-alkyl, C1- C6-alkoxycarbonyl, aminocarbonyl, C1-C6-alkylaminocarbonyl, di-(C1-C6-alkyl)-aminocarbonyl, aminothiocarbonyl, C1-C6-alkylaminosulphonyl, C1-C6-alkylsulphonylamino, C1-C6- alkylcarbonylamino, C1-C4-haloalkylcarbonylamino, C1-C6-alkylthiocarbonylamino, aryl, aryloxy, heteroaryl and heteroaryloxy, represents a radical from the group consisting of halogen, cyano, nitro, amino, hydroxy, C1-C6- alkyl, C1-C6-haloalkyl, cyano-C1-C6-alkyl, C2-C6-alkenyl, C3-C6-alkynyl, C3-C6-cycloalkyl, C3- C6-cycloalkyl-C1-C6-alkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C6-alkenyloxy, C3-C6- alkynyloxy, C3-C6-cycloalkyloxy, C1-C6-alkylcarbonyloxy, C2-C6-alkenylcarbonyloxy, C2-C6- alkynylcarbonyloxy, C3-C6-cycloalkylcarbonyloxy, C1-C6-alkoxycarbonyloxy, C1-C6- alkylsulphonyloxy, C1-C6-alkylamino, C3-C6-alkenylamino, C3-C6-alkynylamino, C3-C6- cycloalkylamino, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C6-alkenylthio, C3-C6-alkynylthio, C3-C6-cycloalkylthio, C1-C6-alkylsulphinyl, C1-C6-alkylsulphonyl, C1-C6-alkylcarbonyl, C1-C6- alkoxyimino-C1-C6-alkyl, C1-C6-alkoxycarbonyl, aminocarbonyl, C1-C6-alkylaminocarbonyl, di- (C1-C6-alkyl)-aminocarbonyl, aminothiocarbonyl, C1-C6-alkylaminosulphonyl, C1-C6- alkylsulphonylamino, C1-C6-alkylcarbonylamino, C1-C6-alkylthiocarbonylamino, aryl, aryloxy, heteroaryl and heteroaryloxy, represents a radical from the group consisting of hydrogen, halogen, amino, hydroxy, C1-C6- alkyl, C1-C6-alkoxy, C1-C6-haloalkyl and C1-C6-haloalkoxy, represents a radical from the group consisting of hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C1- C6-haloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C3-C6-cycloalkyl-C1-C6-alkyl, cyano-C1-C6-alkyl, C1-C6-alkylcarbonyl, C2-C6-alkenylcarbonyl, C1-C6-haloalkylcarbonyl, C2-C6- haloalkenylcarbonyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxycarbonyl, C1-C6-alkylsulphonyl and C1-C6-haloalkylsulphonyl, represents a number from the group consisting of 0, 1, 2 and 3, where for m > 1 the radicals R2 may be identical or different and represents a number from the group consisting of 0, 1, 2 and 3, where for n > 1 the radicals R7 may be identical or different.

Use of compounds of the formula (I) according to Claim 1 in which A represents a radical from the group consisting of

in which the broken line represents the bond to Q and where A furthermore substituents R2, represents a radical from the group consisting of

in which the nitrogen is attached to ring A and the arrow in each case represents the bond to D, D represents the radical of the formula

in which the nitrogen is attached to Q and the arrow represents the bond to B,

B represents a radical from the group consisting of

in which the broken line represents the bond to D and in which B furthermore carries n substituents R7, represents CR8 or represents nitrogen, represents oxygen or sulphur, represents a radical from the group consisting of halogen, cyano, nitro, C1-C6-alkyl, C1-C6- haloalkyl, cyano-C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl- C1-C6-alkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6- cycloalkyloxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulphinyl, C1-C6- alkylsulphonyl, C1-C6-alkoxyimino-C1-C6-alkyl, aryl, aryloxy, heteroaryl and heteroaryloxy, R2 represents a radical from the group consisting of halogen, cyano, nitro, amino, C1-C6-alkyl, C1- C6-haloalkyl, cyano-C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6- cycloalkyl-C1-C6-alkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6-cycloalkyloxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulphinyl, C1-C6- alkylsulphonyl, C1-C6-alkylcarbonyl, di-(C1-C6-alkyl)-amino, C1-C6-alkoxyimino-C1-C6-alkyl, aryl, aryloxy, heteroaryl and heteroaryloxy, R3 represents a radical from the group consisting of hydrogen, halogen, cyano, nitro, amino, C1-C6- alkyl and C1-C6-haloalkyl, R4 represents a radical from the group consisting of hydrogen, halogen, amino, hydroxy, C1-C6- alkyl, C1-C6-alkoxy, C1-C6-haloalkyl and C1-C6-haloalkoxy, R5 represents a radical from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, cyano- C1-C6-alkyl, C2-C6-alkenyl, C3-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, C1- C6-alkylcarbonyl, C2-C6-alkenylcarbonyl, C1-C6-haloalkylcarbonyl, C2-C6-haloalkenylcarbonyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxycarbonyl, C1-C6-alkylsulphonyl, C1-C6- haloalkylsulphonyl and C(=O)-B, R6 represents a radical from the group consisting of hydrogen (only in the radicals B-26, B-33, B- 36 and B-42), halogen, cyano, nitro, hydroxy, carboxyl, C1-C6-alkyl, C1-C6-haloalkyl, cyano- C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, C1- C6-alkoxy, C1-C6-haloalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6-cycloalkyloxy, C1-C6- alkylsulphinyl, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulphonyl, C1-C6-alkylcarbonyl, C1-C6-alkoxyimino-C1-C6-alkyl, C1-C6-alkylcarbonylamino, C1-C6-haloalkylcarbonylamino, aryl, aryloxy, heteroaryl and heteroaryloxy, R7 represents a radical from the group consisting of halogen, cyano, nitro, hydroxy, C1-C6-alkyl, C1-C6-haloalkyl, cyano-C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6- cycloalkyl-C1-C6-alkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6-cycloalkyloxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulphinyl, C1-C6- alkylsulphonyl, C1-C6-alkoxyimino-C1-C6-alkyl, aryl, aryloxy, heteroaryl and heteroaryloxy, R8 represents a radical from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-alkoxy, C1-C6- haloalkyl and C1-C6-haloalkoxy, R9 represents a radical from the group consisting of hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl and C1-C6-haloalkyl, m represents a number from the group consisting of 0, 1, 2 and 3, where for m > 1 the radicals R2 may be identical or different and n represents a number from the group consisting of 0, 1, 2 and 3, where for n > 1 the radicals R7 may be identical or different.

4. Use of compounds of the formula (I) according to Claim 1 in which

A represents a radical from the group consisting of

A-6 A-7

A-12 in which the broken line represents the bond to Q and where A furthermore substituents R2, Q represents a radical from the group consisting of

Q-l Q-2 Q-3 and

Q-5

in which the nitrogen is attached to ring A and the arrow in each case represents the bond to D,

D represents the radical of the formula in which the nitrogen is attached to Q and the arrow represents the bond to B,

B represents a radical from the group consisting of

in which the broken line represents the bond to D and in which B furthermore carries n substituents R7,

Z represents oxygen or sulphur,

Rl represents a radical from the group consisting of halogen, cyano, nitro, C1-C4-alkyl, C1-C4- haloalkyl, C1-C4-alkoxy and C1-C4-alkylsulphonyl,

R2 represents a radical from the group consisting of halogen, C1-C4-alkyl and C1-C4-alkoxy, R3 represents a radical from the group consisting of hydrogen and halogen,

R4 represents a radical from the group consisting of hydrogen and C1-C4-alkyl, R5 represents a radical from the group consisting of hydrogen, C1-C4-alkyl, C3-C i-alkenyl, C3-C4- alkynyl, C3-C6-cycloalkyl-C1-C4-alkyl, C1-C4-alkylcarbonyl, cyano-C1-C4-alkyl and C(=O)-B,

R6 represents a radical from the group consisting of halogen, nitro, hydroxy, C1-C4-alkyl, C1-C4- alkoxy, C1-C4-alkylthio, C1-C4-alkylsulphonyl, C1-C4-haloalkyl, C1-C4-haloalkoxy, C1-C4- haloalkylthio and heteroaryl,

R7 represents a radical from the group consisting of halogen, C1-C4-alkyl and C1-C4-haloalkyl,

R9 represents a radical from the group consisting of C1-C4-alkyl, m represents a number from the group consisting of 0, 1, 2 and 3, where for m > 1 the radicals R2 may be identical or different and n represents a number from the group consisting of 0 and 1.

5. Use of compounds of the formula (I) according to Claim 1 in which

A represents a radical from the group consisting of

A-6

in which the broken line represents the bond to Q and where A furthermore carries m substituents R2,

Q represents a radical from the group consisting of

in which the nitrogen is attached to ring A and the arrow in each case represents the bond to D, D represents the radical of the formula

in which the nitrogen is attached to Q and the arrow represents the bond to B,

B represents a radical from the group consisting of

in which the broken line represents the bond to D and in which B furthermore carries n substituents R7, Z represents oxygen or sulphur, Rl represents a radical from the group consisting of halogen, cyano, nitro, C1-C4-alkyl, C1-C4- haloalkyl, C1-C4-alkoxy and C1-C4-alkylsulphonyl,

R2 represents a radical from the group consisting of halogen, cyano, nitro, amino, C1-C4-alkyl, C1- C4-haloalkyl, C3-C6-cycloalkyl, C1-C4-alkoxy, di-(C1-C6-alkyl)-amino, C1-C4-alkylcarbonyl, aryl,

R3 represents a radical from the group consisting of hydrogen, halogen, cyano, nitro, C1-C4-alkyl,

R4 represents a radical from the group consisting of hydrogen, amino, C1-C4-alkyl,

R5 represents a radical from the group consisting of hydrogen, C1-C4-alkyl, C3-C4-alkenyl, C3-C4- alkynyl, C3-C6-cycloalkyl-C1-C4-alkyl, C1-C4-alkylcarbonyl, cyano-C1-C4-alkyl and C(=O)-B, R6 represents a radical from the group consisting of hydrogen (only in the radicals B-33 and B-36), halogen, cyano, nitro, hydroxy, carboxyl, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4- alkylsulphonyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C1-C4-haloalkoxy, C1-C4-haloalkylthio, C1- C4-alkylcarbonyl, C1-C4-alkylcarbonylamino, C1-C4-haloalkylcarbonylamino and heteroaryl,

R7 represents a radical from the group consisting of halogen, cyano, nitro, hydroxy, C1-C4-alkyl, C1-C4-haloalkyl and C1-C4-alkoxy,

R9 represents a radical from the group consisting of C1-C4-alkyl and C1-C4-haloalkyl, m represents a number from the group consisting of 0, 1, 2 and 3, where for m > 1 the radicals R2 may be identical or different and n represents a number from the group consisting of 0, 1, 2 and 3, where for n > 1 the radicals R7 may be identical or different.

6. Compositions for controlling unwanted microorganisms, characterized in that they comprise at least one compound of the formula (I) as described in any of Claim 1 to 5 and further comprising surfactants and/or extenders.

7. Method for controlling harmful microorganisms, characterized in that one or more compound of the formula (I) according to any of Claim 1 to 5 or a composition according to Claim 6 are applied to the harmful microorganisms or their habitat.

8. Use of one or more compounds according to any of Claim 1 to 5 or a composition according to Claim 6 for control of harmful phytopathogenic fungi.

9. Process for producing compositions for controlling harmful microorganisms, characterized in that one or more compounds according to any of Claims 1 to 5 are mixed with auxiliaries, solvents, carriers, surfactants and/or extenders .

10. Use of one or more compounds which are defined according to any of Claims 1

composition as defined according to Claim 6 for treatment of transgenic plants.

Description:
Heterocyclic compounds for the control of unwanted microorganisms

The present application relates to the use of heterocyclic compounds for controlling harmful microorganisms in plants, compositions comprising these compounds and to processes for preparation of suitable compositions for the control of harmful microorganisms.

The heterocyclic compounds of the formulae (W) and (W2) are known (cf. for the compounds of the formula (W) Registry Numbers 1189645-25-7, 1189474-83-6, 1193202-69-5, 1172407-07-6, 1185158- 40-0, 1185036-12-7, 1170986-74-9, 1193179-17-7, 1189458-68-1, 1189956-23-7, 1189915-26-1, 1170047-96-7). A use of these compounds has not been described.

No. R E

W-l ethyl 2-(trifluoromethyl)phenyl

W-2 ethyl 2-bromophenyl

W-3 ethyl 2-fluorophenyl

W-4 ethyl 3 -methyl-2-thienyl

W-5 ethyl 2,5-dimethyl-3-furanyl

W-6 H 2,4-dimethoxyphenyl

W-7 H 2-(trifluoromethyl)phenyl

W-8 H 2,4-difluorophenyl

W-9 methyl 2-bromophenyl

W-10 ethyl 2,4-difluorophenyl

W-l l H 2,5-dimethyl-3-furanyl

W-12 methyl 2,4-dimethoxyphenyl

In EP 274642, is described the preparation of 4-(aminomethylene)-2-pyrazolin-5-ones as herbicides and fungicides, which are not part of the herein-disclosed invention, 118031-35-9, Ex. VI-136 is described but no biological data are provided.

However the ecological and economic demands made on modern active ingredients, for example fungicides, are increasing constantly, for example with respect to activity spectrum, toxicity, selectivity, application rate, formation of residues and favourable manufacture.

Thus, there is a constant need for developing new, alternative plant protection products which in some areas at least help to fulfill the above-mentioned requirements.In view of this, it was in particular an object of the present invention to provide compounds which exhibit activity against harmful microorganisms in plants, in the protection of materials. Moreover, it was a further particular object of the present invention, to reduce the application rates and broaden the activity spectrum of the fungicides, and thereby to provide compounds which, preferably at a reduced total amount of active compound applied, has improved activity against harmful microorganisms. In particular, it was a further object of the present invention to provide compounds which, when applied to a crop, results in a decreased amount of residues in the crop, and nevertheless provides efficient control of unwanted microorganisms. PCT/EP2013/07031 describes the compounds as shown below as pesticides being active against animal pests including insects and nematodes. As animal pests and harmful microorganisms are very different in many aspects such as physiology, genetics and lifestyle the skilled person would not expect that compounds showing pesticidal activity would also be active against unwanted microorganisms.

This object, and further objects which are not stated explicitly but can be discerned or derived from the connections discussed herein, are achieved by the use of known compounds of the formula (I)

in which

A represents a radical from the group consisting of

in which the broken line represents the bond to Q and in which A furthermore substituents R2, represents a radical from the group consisting of

in which the nitrogen is attached to ring A and the arrow in each case represents the bond to D and

D represents the radical of the formula

in which the nitrogen is attached to Q and the arrow represents the bond to B,

B represents a radical from the group consisting of

in which the broken line represents the bond to D and in which B furthermore carries n substituents R7,

Y represents CR8 or represents nitrogen,

Z represents oxygen or sulphur,

Rl represents a radical from the group consisting of halogen, cyano, nitro, amino, hydroxy, represents C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 3 -C 6 - alkenyloxy, C 3 -C 6 -alkynyloxy, C 3 -C 6 -cycloalkyloxy, C 1 -C 6 -alkylcarbonyloxy, C 2 -C 6 - alkenylcarbonyloxy, C 2 -C 6 -alkynylcarbonyloxy, C 3 -C 6 -cycloalkylcarbonyloxy, C 1 -C 6 - alkoxycarbonyloxy, C 1 -C 6 -alkylsulphonyloxy, C 1 -C 6 -alkylamino, C 3 -C 6 -alkenylamino, C 3 -C 6 - alkynylamino, C 3 -C 6 -cycloalkylamino, C 1 -C 6 -alkylcarbonylamino, C 2 -C 6 -alkenylcarbonylamino, C 2 -C 6 -alkynylcarbonylamino, C 3 -C 6 -cycloalkylcarbonylamino, C 1 -C 6 -alkoxycarbonylamino, C 1 - C 6 -alkylsulphonylamino, C 1 -C 6 -alkylthio, C 3 -C 6 -alkenylthio, C 3 -C 6 -alkynylthio, C 3 -C 6 - cycloalkylthio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 - alkoxyimino-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxycarbonyl, aminocarbonyl, C 1 -C 6 -alkylaminocarbonyl, di- (C 1 -C 6 -alkyl)-aminocarbonyl, aminothiocarbonyl, C 1 -C 6 -alkylaminosulphonyl, C 1 -C 6 - alkylsulphonylamino, C 1 -C 6 -alkylcarbonylamino, C 1 -C 6 -alkylthiocarbonylamino, C 4 -C 12 - bicycloalkyl, aryl, aryloxy, arylamino, arylthio, heteroaryl, heteroaryloxy, heteroarylamino and heteroarylthio, each of which is optionally substituted by one or more identical or different substituents, where the substituents independently of one another are selected from the group consisting of halogen, cyano, nitro, hydroxy, amino, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 3 -C 6 - cycloalkyl, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, aryl, aryloxy, arylthio, heteroaryl, heteroaryloxy and heteroarylthio, represents a radical from the group consisting of halogen, cyano, nitro, amino, hydroxy, represents C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 3 -C 6 - alkenoxy, C 3 -C 6 -alkynoxy, C 3 -C 6 -cycloalkoxy, C 1 -C 6 -alkylcarbonyloxy, C 2 -C 6 - alkenylcarbonyloxy, C 2 -C 6 -alkynylcarbonyloxy, C 3 -C 6 -cycloalkylcarbonyloxy, C 1 -C 6 - alkoxycarbonyloxy, C 1 -C 6 -alkylsulphonyloxy, C 1 -C 6 -alkylamino, di-(C 1 -C 6 -alkyl)-amino, C 3 - C 6 -alkenylamino, C 3 -C 6 -alkynylamino, C 3 -C 6 -cycloalkylamino, C 1 -C 6 -alkylcarbonylamino, C 2 - C 6 -alkenylcarbonylamino, C 2 -C 6 -alkynylcarbonylamino, C 3 -C 6 -cycloalkylcarbonylamino, C 1 - C 6 -alkoxycarbonylamino, C 1 -C 6 -alkylsulphonylamino, C 1 -C 6 -alkylthio, C 3 -C 6 -alkenylthio, C 3 - C 6 -alkynylthio, C 3 -C 6 -cycloalkylthio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 1 -C 6 - alkylcarbonyl, C 1 -C 6 -alkoxyimino-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxycarbonyl, aminocarbonyl, C 1 -C 6 - alkylaminocarbonyl, di-(C 1 -C 6 -alkyl)-aminocarbonyl, aminothiocarbonyl, C 1 -C 6 - alkylaminosulphonyl, C 1 -C 6 -alkylsulphonylamino, C 1 -C 6 -alkylcarbonylamino, C 1 -C 6 - alkylthiocarbonylamino, C 4 -C 12 -bicycloalkyl, aryl, aryloxy, arylamino, arylthio, heteroaryl, heteroaryloxy, heteroarylamino and heteroarylthio, each of which is optionally substituted by one or more identical or different substituents, where the substituents independently of one another are selected from the group consisting of halogen, cyano, nitro, hydroxy, amino, C 1 -C 6 - alkyl, C 1 -C 6 -alkoxy, C 3 -C 6 -cycloalkyl, C 1 -C 6 -haloalkoxy and C 1 -C 6 -alkylthio, aryl, aryloxy, arylthio, heteroaryl, heteroaryloxy and heteroarylthio, represents a radical from the group consisting of hydrogen, halogen, cyano, nitro, amino, hydroxy, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkyl and C 1 -C 6 -haloalkoxy, represents a radical from the group consisting of hydrogen, halogen, amino, hydroxy, C 1 -C 6 - alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkyl and C 1 -C 6 -haloalkoxy, represents a radical from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 - C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl, cyano-C 1 -C 6 -alkyl, C 1 -C 6 -alkylcarbonyl, C 2 -C 6 -alkenylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 2 -C 6 - haloalkenylcarbonyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylsulphonyl and C 1 -C 6 -haloalkylsulphonyl or represents C(=O)-B,

R6 represents a radical from the group consisting of hydrogen (only in the radicals B-26, B-33, B- 36 and B-42), halogen, cyano, nitro, amino, hydroxy, carboxyl, represents C 1 -C 6 -alkyl, C 2 -C 6 - alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 3 -C 6 -alkenoxy, C 3 -C 6 -alkynoxy, C 3 - C 6 -cycloalkoxy, C 1 -C 6 -alkylcarbonyloxy, C 2 -C 6 -alkenylcarbonyloxy, C 2 -C 6 - alkynylcarbonyloxy, C 3 -C 6 -cycloalkylcarbonyloxy, C 1 -C 6 -alkoxycarbonyloxy, C 1 -C 6 - alkylsulphonyloxy, C 1 -C 6 -alkylcarbonylamino, C 2 -C 6 -alkenylcarbonylamino, C 2 -C 6 - alkynylcarbonylamino, C 3 -C 6 -cycloalkylcarbonylamino, C 1 -C 6 -alkoxycarbonylamino, C 1 -C 6 - alkylsulphonylamino, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 1 -C 6 - alkylcarbonyl, C 1 -C 6 -alkoxyimino-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxycarbonyl, aminocarbonyl, C 1 -C 6 - alkylaminocarbonyl, di-(C 1 -C 6 -alkyl)-aminocarbonyl, aminothiocarbonyl, C 1 -C 6 - alkylaminosulphonyl, C 1 -C 6 -alkylsulphonylamino, C 1 -C 6 -alkylcarbonylamino, C 1 -C 6 - haloalkylcarbonylamino, C 1 -C 6 -alkylthiocarbonylamino, C4-Ci2-bicycloalkyl, aryl, aryloxy, heteroaryl, heteroaryloxy, each of which is optionally substituted by one or more identical or different substituents, where the substituents independently of one another are selected from the group consisting of halogen, cyano, nitro, hydroxy, amino, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 3 -C 6 - cycloalkyl, C 1 -C 6 -haloalkoxy and C 1 -C 6 -alkylthio,

R7 represents a radical from the group consisting of halogen, nitro, cyano, amino, hydroxy, represents C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 3 -C 6 - alkenoxy, C 3 -C 6 -alkynoxy, C 3 -C 6 -cycloalkoxy, C 1 -C 6 -alkylcarbonyloxy, C 2 -C 6 - alkenylcarbonyloxy, C 2 -C 6 -alkynylcarbonyloxy, C 3 -C 6 -cycloalkylcarbonyloxy, C 1 -C 6 - alkoxycarbonyloxy, C 1 -C 6 -alkylsulphonyloxy, C 1 -C 6 -alkylcarbonylamino, C 2 -C 6 - alkenylcarbonylamino, C 2 -C 6 -alkynylcarbonylamino, C 3 -C 6 -cycloalkylcarbonylamino, C 1 -C 6 - alkoxycarbonylamino, C 1 -C 6 -alkylsulphonylamino, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulphinyl, C 1 - C 6 -alkylsulphonyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxyimino-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxycarbonyl, aminocarbonyl, C 1 -C 6 -alkylaminocarbonyl, di-(C 1 -C 6 -alkyl)-aminocarbonyl, aminothiocarbonyl, C 1 -C 6 -alkylaminosulphonyl, C 1 -C 6 -alkylsulphonylamino, C 1 -C 6 -alkylcarbonylamino, C 1 -C 6 - alkylthiocarbonylamino, aryl, aryloxy, heteroaryl, heteroaryloxy, C i-Ci2-bicycloalkyl, each of which is optionally substituted by one or more identical or different substituents, where the substituents independently of one another are selected from the group consisting of halogen, cyano, nitro, hydroxy, amino, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 3 -C 6 -cycloalkyl, C 1 -C 6 -haloalkoxy and C 1 -C 6 -alkylthio,

R8 represents a radical from the group consisting of hydrogen, halogen, amino, hydroxy, C 1 -C 6 - alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkyl and C 1 -C 6 -haloalkoxy, R9 represents a radical from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, haloalkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl, cyano-C 1 -C 6 -alkyl, C 1 - C 6 -alkylcarbonyl, C 2 -C 6 -alkenylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 2 -C 6 -haloalkenylcarbonyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylsulphonyl and C 1 -C 6 - haloalkylsulphonyl, m represents a number from the group consisting of 0, 1, 2 and 3, where for m > 1 the radicals R2 may be identical or different and n represents a number from the group consisting of 0, 1, 2 and 3, where for n > 1 the radicals R7 may be identical or different, for controlling unwanted microorganisms.

It has been found that the known compounds of the formula (I) have pronounced biological properties and are suitable especially for controlling unwanted microorganisms, in particular phytopathogenic fungi, phytopathogenic bacteria, phytopathogenic oomycetes, and phytopathogenic viruses , encountered in agriculture, in forests, in the protection of stored products and materials. The invention also comprises a method for preparing an agricultural composition comprising adding agriculturally suitable components such as suitable extenders, solvents, spontaneity promoters, carriers, emulsifiers, dispersants, frost protectants, thickeners, adjuvants or the like to the composition according to the invention. Furthermore the invention comprises a method for reducing damage of plants and plant parts or losses in harvested fruits or vegetables caused by harmful microorganisms by controlling such harmful microorganisms, comprising applying the compounds to the plant or the harmful microorganisms or the habitat of the plant or the habitat of the harmful microorganisms.

In view of this, the problem underlying the present invention has been solved by using known compounds which exhibit fungicidal activity against harmful microorganisms in plants, in the protection of materials. Moreover, the novel compositions according to the invention enable reduced application rates and broaden the activity spectrum of the fungicides. Finally the new use of the known compounds provide improved activity harmful microorganisms and consequently provide efficient disease control for reducing damage of plants and plant parts or losses in harvested fruits or vegetables.

The compounds of the formula (I) may, where appropriate, depending on the nature of the substituents, be in the form of geometric and/or optically active isomers or corresponding isomer mixtures of varying composition. The invention relates both to the use of the pure isomers and to that of the isomer mixtures. Preferred substituents or ranges for the radicals shown in the compounds of the formula (I) to be used for controlling harmful microorganisms are illustrated below.

A represents a radical from the group consisting of

in which the broken line represents the bond to Q and where A furthermore carries m substituents R2, represents a radical from the group consisting of

in which the nitrogen is attached to ring A and the arrow in each case represents the bond to D,

D represents the radical of the formula

in which the nitrogen is attached to Q and the arrow represents the bond to B.

B represents a radical from the group consisting of

in which the broken line represents the bond to D and in which B furthermore carries n substituents R7. represents CR8 or represents nitrogen, represents oxygen or sulphur. represents a radical from the group consisting of halogen, cyano, nitro, amino, hydroxy, C 1 -C 6 - alkyl, C 1 -C 6 -haloalkyl, cyano-C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 - C 6 -cycloalkyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 - alkynyloxy, C 3 -C 6 -cycloalkyloxy, C 1 -C 6 -alkylcarbonyloxy, C 2 -C 6 -alkenylcarbonyloxy, C 2 -C 6 - alkynylcarbonyloxy, C 3 -C 6 -cycloalkylcarbonyloxy, C 1 -C 6 -alkoxycarbonyloxy, C 1 -C 6 - alkylsulphonyloxy, C 1 -C 6 -alkylamino, C 3 -C 6 -alkenylamino, C 3 -C 6 -alkynylamino, C 3 -C 6 - cycloalkylamino, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 3 -C 6 -alkenylthio, C 3 -C 6 -alkynylthio, C 3 -C 6 -cycloalkylthio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 - alkoxyimino-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxycarbonyl, aminocarbonyl, C 1 -C 6 -alkylaminocarbonyl, di- (C 1 -C 6 -alkyl)-aminocarbonyl, aminothiocarbonyl, C 1 -C 6 -alkylaminosulphonyl, C 1 -C 6 - alkylsulphonylamino, C 1 -C 6 -alkylcarbonylamino, C 1 -C 6 -alkylthiocarbonylamino, aryl, aryloxy, heteroaryl and heteroaryloxy. represents a radical from the group consisting of halogen, cyano, nitro, amino, hydroxy, C 1 -C 6 - alkyl, C 1 -C 6 -haloalkyl, cyano-C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 - C 6 -cycloalkyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 - alkynyloxy, C 3 -C 6 -cycloalkyloxy, C 1 -C 6 -alkylcarbonyloxy, C 2 -C 6 -alkenylcarbonyloxy, C 2 -C 6 - alkynylcarbonyloxy, C 3 -C 6 -cycloalkylcarbonyloxy, C 1 -C 6 -alkoxycarbonyloxy, C 1 -C 6 - alkylsulphonyloxy, C 1 -C 6 -alkylamino, di-(C 1 -C 6 -alkyl)-amino, C 3 -C 6 -alkenylamino, C 3 -C 6 - alkynylamino, C 3 -C 6 -cycloalkylamino, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 3 -C 6 -alkenylthio, C 3 -C 6 -alkynylthio, C 3 -C 6 -cycloalkylthio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 1 -C 6 - alkylcarbonyl, C 1 -C 6 -alkoxyimino-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxycarbonyl, aminocarbonyl, C 1 -C 6 - alkylaminocarbonyl, di-(C 1 -C 6 -alkyl)-aminocarbonyl, aminothiocarbonyl, C 1 -C 6 - alkylaminosulphonyl, C 1 -C 6 -alkylsulphonylamino, C 1 -C 6 -alkylcarbonylamino, C 1 -C 6 - alkylthiocarbonylamino, aryl, aryloxy, heteroaryl and heteroaryloxy. represents a radical from the group consisting of hydrogen, halogen, cyano, nitro, amino, C 1 -C 6 - alkyl and C 1 -C 6 -haloalkyl. represents a radical from the group consisting of hydrogen, halogen, amino, hydroxy, C 1 -C 6 - alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkyl and C 1 -C 6 -haloalkoxy. represents a radical from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, cyano- C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl, C 1 - C 6 -alkylcarbonyl, C 2 -C 6 -alkenylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 2 -C 6 -haloalkenylcarbonyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylsulphonyl, C 1 -C 6 - haloalkylsulphonyl and C(=O)-B. represents a radical from the group consisting of hydrogen (only in the radicals B-26, B-33, B- 36 and B-42), halogen, cyano, nitro, amino, hydroxy, carboxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, cyano-C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 6 - alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -alkynyloxy, C 3 -C 6 - cycloalkyloxy, C 1 -C 6 -alkylcarbonyloxy, C 2 -C 6 -alkenylcarbonyloxy, C 2 -C 6 -alkynylcarbonyloxy, C 3 -C 6 -cycloalkylcarbonyloxy, C 1 -C 6 -alkoxycarbonyloxy, C 1 -C 6 -alkylsulphonyloxy, C 1 -C 6 - alkylamino, C 3 -C 6 -alkenylamino, C 3 -C 6 -alkynylamino, C 3 -C 6 -cycloalkylamino, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 3 -C 6 -alkenylthio, C 3 -C 6 -alkynylthio, C 3 -C 6 -cycloalkylthio, C 1 -C 6 - alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxyimino-C 1 -C 6 -alkyl, C 1 - C 6 -alkoxycarbonyl, aminocarbonyl, C 1 -C 6 -alkylaminocarbonyl, di-(C 1 -C 6 -alkyl)-aminocarbonyl, aminothiocarbonyl, C 1 -C 6 -alkylaminosulphonyl, C 1 -C 6 -alkylsulphonylamino, C 1 -C 6 - alkylcarbonylamino, C 1 -C 4 -haloalkylcarbonylamino, C 1 -C 6 -alkylthiocarbonylamino, aryl, aryloxy, heteroaryl and heteroaryloxy.

R7 represents a radical from the group consisting of halogen, cyano, nitro, amino, hydroxy, C 1 -C 6 - alkyl, C 1 -C 6 -haloalkyl, cyano-C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 - C 6 -cycloalkyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 - alkynyloxy, C 3 -C 6 -cycloalkyloxy, C 1 -C 6 -alkylcarbonyloxy, C 2 -C 6 -alkenylcarbonyloxy, C 2 -C 6 - alkynylcarbonyloxy, C 3 -C 6 -cycloalkylcarbonyloxy, C 1 -C 6 -alkoxycarbonyloxy, C 1 -C 6 - alkylsulphonyloxy, C 1 -C 6 -alkylamino, C 3 -C 6 -alkenylamino, C 3 -C 6 -alkynylamino, C 3 -C 6 - cycloalkylamino, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 3 -C 6 -alkenylthio, C 3 -C 6 -alkynylthio, C 3 -C 6 -cycloalkylthio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 - alkoxyimino-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxycarbonyl, aminocarbonyl, C 1 -C 6 -alkylaminocarbonyl, di- (C 1 -C 6 -alkyl)-aminocarbonyl, aminothiocarbonyl, C 1 -C 6 -alkylaminosulphonyl, C 1 -C 6 - alkylsulphonylamino, C 1 -C 6 -alkylcarbonylamino, C 1 -C 6 -alkylthiocarbonylamino, aryl, aryloxy, heteroaryl and heteroaryloxy.

R8 represents a radical from the group consisting of hydrogen, halogen, amino, hydroxy, C 1 -C 6 - alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkyl and C 1 -C 6 -haloalkoxy. R9 represents a radical from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 - C 6 -haloalkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl, cyano-C 1 -C 6 -alkyl, C 1 -C 6 -alkylcarbonyl, C 2 -C 6 -alkenylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 2 -C 6 - haloalkenylcarbonyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylsulphonyl and C 1 -C 6 -haloalkylsulphonyl. m represents a number from the group consisting of 0, 1 , 2 and 3, where for m > 1 the radicals R2 may be identical or different. n represents a number from the group consisting of 0, 1 , 2 and 3, where for n > 1 the radicals R7 may be identical or different.

Particularly preferred substituents or ranges for the radicals shown in the compounds of the formula (I) to be used for controlling harmful microorganisms are illustrated below.

A represents a radical from the group consisting of

in which the broken line represents the bond to Q and where A furthermore carries m substituents R2.

Q represents a radical from the group consisting of

in which the nitrogen is attached to ring A and the arrow in each case represents the bond to D. D represents the radical of the formula

in which the nitrogen is attached to Q and the arrow represents the bond to B. represents a radical from the group consisting of

in which the broken line represents the bond to D and in which B furthermore carries n substituents R7.

Y represents CR8 or represents nitrogen. Z represents oxygen or sulphur.

Rl represents a radical from the group consisting of halogen, cyano, nitro, C 1 -C 6 -alkyl, C 1 -C 6 - haloalkyl, cyano-C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 6 - alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -alkynyloxy, C 3 -C 6 -cycloalkyloxy, C 1 - C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 1 -C 6 -alkoxyimino-C 1 - C 6 -alkyl, aryl, aryloxy, heteroaryl and heteroaryloxy. R2 represents a radical from the group consisting of halogen, cyano, nitro, amino, C 1 -C 6 -alkyl, C 1 - C 6 -haloalkyl, cyano-C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 - C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -alkynyloxy, C 3 -C 6 -cycloalkyloxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 1 -C 6 -alkylcarbonyl, di-(C 1 -C 6 -alkyl)-amino, C 1 -C 6 -alkoxyimino-C 1 -C 6 -alkyl, aryl, aryloxy, heteroaryl and heteroaryloxy.

R3 represents a radical from the group consisting of hydrogen, halogen, cyano, nitro, amino, C 1 -C 6 - alkyl and C 1 -C 6 -haloalkyl.

R4 represents a radical from the group consisting of hydrogen, halogen, amino, hydroxy, C 1 -C 6 - alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkyl and C 1 -C 6 -haloalkoxy. R5 represents a radical from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, cyano- C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl, C 1 -C 6 - alkylcarbonyl, C 2 -C 6 -alkenylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 2 -C 6 -haloalkenylcarbonyl, C 1 -C 6 - alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylsulphonyl, C 1 -C 6 -haloalkylsulphonyl and C(=O)- B. R6 represents a radical from the group consisting of hydrogen (only in the radicals B-26, B-33, B- 36 and B-42), halogen, cyano, nitro, hydroxy, carboxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, cyano-C 1 -C 6 - alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 - C 6 -haloalkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -alkynyloxy, C 3 -C 6 -cycloalkyloxy, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 - alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkylsulphonyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxyimino-C 1 -C 6 - alkyl, C 1 -C 6 -alkylcarbonylamino, C 1 -C 6 -haloalkylcarbonylamino, aryl, aryloxy, heteroaryl and heteroaryloxy.

R7 represents a radical from the group consisting of halogen, cyano, nitro, hydroxy, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, cyano-C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl- C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -alkynyloxy, C 3 -C 6 - cycloalkyloxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 1 -C 6 - alkoxyimino-C 1 -C 6 -alkyl, aryl, aryloxy, heteroaryl and heteroaryloxy.

R8 represents a radical from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 - haloalkyl and C 1 -C 6 -haloalkoxy.

R9 represents a radical from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl and C 1 -C 6 -haloalkyl. m represents a number from the group consisting of 0, 1 , 2 and 3, where for m > 1 the radicals R2 may be identical or different. n represents a number from the group consisting of 0, 1, 2 and 3, where for n > 1 the radicals R7 may be identical or different.

Very particularly preferred substituents or ranges of the radicals shown in the compounds of the formula (I) to be used for controlling harmful microorganisms are elucidated below.

A represents a radical from the group consisting of

in which the broken line represents the bond to Q and where A furthermore substituents R2. represents a radical from the group consisting of

in which the nitrogen is attached to ring A and the arrow in each case represents the bond to D.

D represents the radical of the formula

in which the nitrogen is attached to Q and the arrow represents the bond to B.

B represents a radical from the group consisting of

in which the broken line represents the bond to D and in which B furthermore carries n substituents R7.

Z represents oxygen or sulphur.

Rl represents a radical from the group consisting of halogen, cyano, nitro, C 1 -C 4 -alkyl, C1-C4- haloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -alkylsulphonyl.

R2 represents a radical from the group consisting of halogen, C 1 -C 4 -alkyl and C 1 -C 4 -alkoxy. R3 represents a radical from the group consisting of hydrogen and halogen. R4 represents a radical from the group consisting of hydrogen and C 1 -C 4 -alkyl.

R5 represents a radical from the group consisting of hydrogen, C 1 -C 4 -alkyl, C 3 -C4-alkenyl, C 3 -C4- alkynyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkylcarbonyl, cyano-C 1 -C 4 -alkyl and C(=O)-B. R6 represents a radical from the group consisting of halogen, nitro, hydroxy, C 1 -C 4 -alkyl, C1-C4- alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkylthio and heteroaryl.

R7 represents a radical from the group consisting of halogen, C 1 -C 4 -alkyl and C 1 -C 4 -haloalkyl. R9 represents a radical from the group consisting of C 1 -C 4 -alkyl. m represents a number from the group consisting of 0, 1 , 2 and 3, where for m > 1 the radicals R2 may be identical or different. n represents a number from the group consisting of 0 and 1.

A further group of very particularly preferred substituents or ranges of the radicals shown in the compounds of the formula (I) to be used for controlling harmful microorganisms are illustrated below.

A represents a radical from the group consisting of

in which the broken line represents the bond to Q and where A furthermore carries m substituents R2,

Q represents a radical from the group consisting of

in which the nitrogen is attached to ring A and the arrow in each case represents the bond to D. D represents the radical of the formula

in which the nitrogen is attached to Q and the arrow represents the bond to B.

B represents a radical from the group consisting of

in which the broken line represents the bond to D and in which B furthermore carries n substituents R7. Z represents oxygen or sulphur. Rl represents a radical from the group consisting of halogen, cyano, nitro, C 1 -C 4 -alkyl, C1-C4- haloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -alkylsulphonyl.

R2 represents a radical from the group consisting of halogen, cyano, nitro, amino, C 1 -C 4 -alkyl, C 1 - C4-haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy, di-(C 1 -C 6 -alkyl)-amino, acetyl, aryl. R3 represents a radical from the group consisting of hydrogen, halogen, cyano, nitro, C 1 -C 4 -alkyl.

R4 represents a radical from the group consisting of hydrogen, amino, C 1 -C 4 -alkyl.

R5 represents a radical from the group consisting of hydrogen, C 1 -C 4 -alkyl, C 3 -C4-alkenyl, C 3 -C4- alkynyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkylcarbonyl, cyano-C 1 -C 4 -alkyl and C(=O)-B.

R6 represents a radical from the group consisting of hydrogen (only in the radicals B-33 and B-36), halogen, cyano, nitro, hydroxy, carboxyl, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C1-C4- alkylsulphonyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkylthio, acetyl, C 1 - C4-alkylcarbonylamino, C 1 -C 4 -haloalkylcarbonylamino and heteroaryl.

R7 represents a radical from the group consisting of halogen, cyano, nitro, hydroxy, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl and C 1 -C 4 -alkoxy. R9 represents a radical from the group consisting of Cl-C4-alkyl and Cl-C4-haloalkyl. m represents a number from the group consisting of 0, 1 , 2 and 3, where for m > 1 the radicals R2 may be identical or different. n represents a number from the group consisting of 0, 1, 2 and 3, where for n > 1 the radicals R7 may be identical or different. In the preferred definitions, unless stated otherwise, halogen is selected from the group of fluorine, chlorine, bromine and iodine, preferably in turn from the group of fluorine, chlorine and bromine, aryl (including as part of a larger unit, for example arylalkyl) is selected from the group of phenyl, naphthyl, anthryl, phenanthrenyl, and is preferably in turn phenyl, hetaryl (having the same meaning as heteroaryl, also as part of a relatively large unit such as, for example, heteroaryloxy) is selected from the group consisting of furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1 ,2,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,3- oxadiazolyl, 1 ,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4- thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, pyridyl, pyrimidinyl, pyridazinyl and pyrazinyl. In the particularly preferred definitions, unless stated otherwise, halogen is selected from the group of fluorine, chlorine, bromine and iodine, preferably in turn from the group of fluorine, chlorine and bromine, aryl (including as part of a larger unit, for example arylalkyl) is selected from the group of phenyl, naphthyl, anthryl, phenanthrenyl, and is preferably in turn phenyl, het(ero)aryl (also as part of a relatively large unit such as, for example, heteroaryloxy) is selected from the group consisting of furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, oxadiazolyl, 1,2,3-triazolyl, 1,2,4- triazolyl, oxazolyl, isoxazolyl and thiazolyl.

In the very particularly preferred definitions, unless stated otherwise, halogen is selected from the group consisting of fluorine, chlorine, bromine and iodine, preferably in turn from the group consisting of fluorine, chlorine and bromine, and het(ero)aryl (also as part of a relatively large unit such as, for example, heteroaryloxy) represents 1 ,2,4- triazolyl.

Halogen-substituted radicals, for example haloalkyl, are mono- or polyhalogenated, up to the maximum number of possible substituents. In the case of polyhalogenation, the halogen atoms may be identical or different. Halogen denotes fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine and bromine.

Saturated or unsaturated hydrocarbyl radicals, such as alkyl or alkenyl, may in each case be straight- chain or branched as far as possible, including in combination with heteroatoms, as, for example, in alkoxy.

Optionally substituted radicals may be mono- or polysubstituted, where the substituents in the case of polysubstitution may be the same or different.

The radical definitions or elucidations given above in general terms or within areas of preference apply to the end products and correspondingly to the starting materials and intermediates. These radical definitions can be combined with one another as desired, i.e. including combinations between the respective preferred ranges.

Preference according to the invention is given to using compounds of the formula (I) which contain a combination of the meanings listed above as being preferred.

Particular preference according to the invention is given to using compounds of the formula (I) which contain a combination of the meanings listed above as being particularly preferred. Very particular preference according to the invention is given to using compounds of the formula (I) which contain a combination of the meanings listed above as being very particularly preferred.

The present invention also provides novel compounds of the formula (I) in which A, Q, D and B have the meanings mentioned above, except for the compounds W and W2 described above, in particular W-l to W-12, W2-1 to W2-3, W2-5 and W2-6. The general or preferred radical definitions or elucidations listed above also apply to the novel compounds of the formula (I). If compounds to be used in accordance with the invention are mentioned in the present application, this includes, unless indicated otherwise, in each case both the compounds of the formula (I) and the novel compounds of the formula (I). In the groups of compounds below, the individual radicals R and Z have the meanings given above.

In a particular group of compounds of the formula (I) to be used in accordance with the invention, Q represents Q-1

In a further particular group of compounds of the formula (I) to be used in accordance with the invention, Q represents Q-2

In a further particular group of compounds of the formula (I) to be used in accordance with the invention, Q represents Q-3

In a further particular group of compounds of the formula (I) to be used in accordance with the invention, Q represents Q-4

In a further particular group of compounds of the formula (I) to be used in accordance with the invention, Q represents Q-5

In a further particular group of compounds of the formula (I) to be used in accordance with the invention, A represents

where this radical carries m substituents R2.

In a further particular group of compounds of the formula (I) to be used in accordance with the invention, A represents

where this radical carries m substituents R2. In a further particular group of compounds of the formula (I) to be used in accordance with the invention, A represents

where this radical carries m substituents R2. In the particular groups of compounds of the formula (I) below, all of which represent preferred embodiments, the radicals A and B may carry further substituents R2 and R7, respectively, as specified above.

A particular group of compounds of the formula (I) are compounds of the formula (A-1)-(Q-1)-D-(B-1)

A further particular group of compounds of the formula (I) are compounds of the formula (A-2)-(Q-l)- D-(B-l)

A further particular group of compounds of the formula (I) are compounds of the formula (A-l)-(Q-l)- D-(B-2)

A further particular group of compounds of the formula (I) are compounds of the formula (A-l)-(Q-l)- D-(B-39)

A further particular group of compounds of the formula (I) are compounds of the formula (A-l)-(Q-l)- D-(B-23)

A further particular group of compounds of the formula (I) are compounds of the formula (A-l)-(Q-l)- D-(B-21)

A further particular group of compounds of the formula (I) are compounds of the formula (A-l)-(Q-l)- D-(B-18)

A further particular group of compounds of the formula (I) are compounds of the formula (A-l)-(Q-l)- D-(B-3)

A further particular group of compounds of the formula (I) are compounds of the formula (A-l)-(Q-l)- D-(B-l l)

A further particular group of compounds of the formula (I) are compounds of the formula (A-l)-(Q-l)- D-(B-5)

A further particular group of compounds of the formula (I) are compounds of the formula (A-6)-(Q-l)- D-(B-l)

A further particular group of compounds of the formula (I) are compounds of the formula (A-2)-(Q-l)- D-(B-3)

A further particular group of compounds of the formula (I) are compounds of the formula (A-l)-(Q-4)- D-(B-l)

A further particular group of compounds of the formula (I) are compounds of the formula (A-l)-(Q-2)- D-(B-l)

A further particular group of compounds of the formula (I) are compounds of the formula (A-l)-(Q-2)- D-(B-5)

A further particular group of compounds of the formula (I) are compounds of the formula (A-2)-(Q-5)-

D-(B-l)

In the same manner as for the particular groups of compounds above, the respective structural formulae may be constructed in a simple manner for the groups of compounds below.

A further particular group of compounds of the formula (I) are compounds of the formula (A-3)-(Q-l)-

D-(B-l).

A further particular group of compounds of the formula (I) are compounds of the formula (A-l)-(Q-l)- D-(B-36). A further particular group of compounds of the formula (I) are compounds of the formula (A-l)-(Q-l)- D-(B-46).

A further particular group of compounds of the formula (I) are compounds of the formula (A-l)-(Q-l)-

D-(B-l).

A further particular group of compounds of the formula (I) are compounds of the formula (A-l)-(Q-l)- D-(B-27).

A further particular group of compounds of the formula (I) are compounds of the formula (A-l)-(Q-l)- D-(B-51).

A further particular group of compounds of the formula (I) are compounds of the formula (A-l)-(Q-l)- D-(B-4).

A further particular group of compounds of the formula (I) are compounds of the formula (A-l)-(Q-l)- D-(B-13).

A further particular group of compounds of the formula (I) are compounds of the formula (A-l)-(Q-l)- D-(B-31). A further particular group of compounds of the formula (I) are compounds of the formula (A-l)-(Q-l)- D-(B-35).

A further particular group of compounds of the formula (I) are compounds of the formula (A-l)-(Q-l)- D-(B-27). A further particular group of compounds of the formula (I) are compounds of the formula (A-l)-(Q-l)- D-(B-IO).

A further particular group of compounds of the formula (I) are compounds of the formula (A-l)-(Q-l)- D-(B-51).

A further particular group of compounds of the formula (I) are compounds of the formula (A-12)-(Q-1)- D-(B-l).

A further particular group of compounds of the formula (I) are compounds of the formula (A-12)-(Q-1)- D-(B-2).

A further particular group of compounds of the formula (I) are compounds of the formula (A-2)-(Q-l)- D-(B-49). A further particular group of compounds of the formula (I) are compounds of the formula (A-2)-(Q-l)- D-(B-46).

A further particular group of compounds of the formula (I) are compounds of the formula (A-2)-(Q-l)- D-(B-13).

A further particular group of compounds of the formula (I) are compounds of the formula (A-2)-(Q-l)- D-(B-4).

A further particular group of compounds of the formula (I) are compounds of the formula (A-2)-(Q-l)- D-(B-6).

A further particular group of compounds of the formula (I) are compounds of the formula (A-2)-(Q-l)- D-(B-25). A further particular group of compounds of the formula (I) are compounds of the formula (A-2)-(Q-l)- D-(B-31).

A further particular group of compounds of the formula (I) are compounds of the formula (A-2)-(Q-l)- D-(B-35). A further particular group of compounds of the formula (I) are compounds of the formula (A-2)-(Q-l)- D-(B-27).

A further particular group of compounds of the formula (I) are compounds of the formula (A-7)-(Q-l)- D-(B-l). A further particular group of compounds of the formula (I) are compounds of the formula (A-9)-(Q-l)- D-(B-l).

A further particular group of compounds of the formula (I) are compounds of the formula (A-2)-(Q-l)- D-(B-31).

A further particular group of compounds of the formula (I) are compounds of the formula (A-2)-(Q-l)- D-(B-35).

If R4 or R3 in group Q-1 represents hydroxy, Q-1 may also be present in the keto form:

The compounds of the formula (I) can be obtained by the processes described in PCT/EP2013/070371. The compounds according to formula (I) are prepared by processes in which Z represents O,

where A, Q, D and B have the meanings described above, by reacting amines of the formulae (II- 1) to (Π-5)

with carboxylic acids or carbonyl halides of the formula (III)

in which

M represents halogen, hydroxy, alkoxy, alkylsulphanyl, acyloxy, sulphonyloxy, N-heterocyclyl (e.g. imidazolyl) or represents hydroxy,

B has the meanings given above and

Z represents O. Here, compounds of the formula (III) can be preactivated or be activated in situ. Compounds of the formula (III) can be employed, for example, as acid halides (e.g. M = chlorine). In this case, the reaction is advantageously carried out in the presence of a base such as, for example, triethylamine or sodium hydroxide. However, it is also possible to use carboxylic acids (M = OH) in the presence of coupling reagents such as, for example dicyclohexylcarbodiimide and additives such as 1 -hydroxy- 1-H- benzotriazole (W. Konig, R. Geiger, Chem. Ber. 1970, 103, 788). Use may furthermore be made of coupling reagents such as l-ethyl-3-(3-dimethylaminopropyl)carbodiimide, 1,1 ' -carbonyl- lH-imidazole, 0-(benzotriazol-l -yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate and similar compounds. Suitable coupling reagents for carrying out the preparation process are, in principle, all compounds which allow an amide bond to be formed (cf, for example, E. Valeur, M. Bradley Chem. Soc. Rev. 2009, 38, 606; S.-Y. Han, Y.-A. Kim Tetrahedron 2004, 60, 2447). Use may furthermore also be made of symmetric or mixed anhydrides for preparing compounds of the formula (I) (G. W. Anderson, J. E. Zimmerman, F. M. Calahan, J. Am. Chem. Soc. 1967, 89, 5012). Here, various chloro formic esters may be employed, for example isobutyl chloroformate and sec-butyl chloroformate. Isovaleryl chloride and pivaloyl chloride, for example, may likewise be used. b) The compounds of the formula (I) in which Z represents O (oxygen atom) can then optionally be reacted with a sulphurizing agent such as diphosphorus pentasulphide or Lawesson's reagent (cf. C. P. Dell in Comprehensive Organic Functional Group Transformations, Vol. 5, eds.: A. L. Katritzky, O. Meth-Cohn, C. W. Rees, Pergamon, Oxford, 1995, S. 565; M. Jesberger, T. P. Davis, L. Barner, Synthesis 2003, 13, 1929), to give compounds of the formula (I) in which Z represents S (sulphur atom). c) Compounds of the formulae (1-1), (1-2) and (1-3)

in which R3 represents halogen can be obtained either via the preparation route described above from the corresponding amines of the formulae (II- 1), (Π-2) and (Π-3) in which R3 represents halogen (F, CI, Br or I), or be synthesized from amides of the formulae (1-1), (1-2) and (1-3) in which R3 represents H (hydrogen) by reaction with a halogenating agent such as N-halosuccinimides (cf, for example, WO2008/092888, Z.-G- Zhao, Z.-X. Wang, Synth. Comm. 2007, 37, 137) or 1 -chloromethyl-4- fluorodiazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (P. T. Nyffeler, S. Gonzalez Duron, M. D. Burkart, S. P. Vincent, C-H. Wong, Angew. Chem. Int. Ed. 2005, 44, 192). d) Compounds of the formulae (1-1), (1-2) and (1-3) in which R5 represents hydrogen, can be converted in the presence of a base (for example sodium hydride) and an alkylating (for example methyl iodide) or acylating agent (for example acetic anhydride) into compounds of the formulae (1-1), (1-2) and (1-3) in which R5 represents alkyl or acyl (cf, for example, WO 2005/092863). e) Compounds of the formula (1-1) can alternatively also be obtained by reacting lH-pyrazoles of the formula (IV- 1)

with aromatics or heteroaromatics of the formula (V)

which are substituted by a suitable group LG. The reaction can be carried out either in the presence of a base (for example potassium carbonate for, for instance, LG = fluorine (cf. WO 2011/060035) or optionally a catalyst (for example CuI/l,2-cyclohexanediamine, potassium carbonate for, for instance, LG = bromine (cf. WO 2007/039146) or Cu(OAc) 2 /pyridine for, for instance, LG = B(OH) 2 (cf. WO 2005/092863)).

Amines of the formula (II- 1)

are commercially available or known from the literature, or they can be synthesized by processes known from the literature.

The lH-pyrazole-3 -amines of the formula (II- 1) can be obtained as shown in Synthesis Scheme 1.

According to route A-1 , lH-pyrazole-3 -amines of the formula (1 -1) can be reacted with aromatics or heteroaromatics of the formula (1 -2) substituted with a suitable group LG 1 to react, in the presence of a base (for example potassium teri-butoxide for, for instance, LG 1 = chlorine (cf. WO 2009/012482) or, for example, caesium carbonate for, for instance, LG 1 = chlorine (cf. WO 2007/056155)) and optionally a catalyst (for example CuI/N,N-dimethylethane-l ,2-diamine, potassium carbonate for, for instance, LG 1 = iodine (cf. WO2008/153042) or Pd2(dba)3/xantphos, sodium carbonate for, for instance, LG 1 = chlorine (cf. Z. Shen, Y. Hong, X. He, W. Mo, B. Hu, N. Sun, X. Hu, Org. Lett. 2010, 12, 552)) to give compounds of the formula (II- 1).

In an alternative route B-l, an aryl- or hetarylhydrazine of the formula (1-3), which may be present as free hydrazine or as a salt (for example as hydrochloride) can be reacted with an acrylonitrile of the formula (1-4) which is substituted by a leaving group LG 2 (for instance LG 2 = OR where R = alkyl, acyl, sulphonyl, etc.; LG 2 = SR where R = alkyl, acyl, etc.; LG 2 = NHR or NR 2 where R = alkyl, acyl, sulphonyl; LG 2 = halogen or cyano) in the presence of a suitable base (for example sodium ethoxide, cf, for instance, WO 2004/037794 or potassium tert-butoxide, cf, for instance, WO 2008/046527) to give the lH-pyrazole-3 -amine of the formula (II-l). 4,5-Dihydro-lH-pyrazole-3-amines of the formula (II-4) in which Y represents N can be prepared via route C-l from aryl- or hetarylhydrazines (1-3) which can be present as free hydrazines or salts (for example as hydrochlorides) using acrylonitriles of the formula (1-5) in the presence of a suitable base (for example choline) (cf. C. Albert, C. Tironi, Farmaco Sci. 1964 , 19, 618). Compounds of the formula (II-4) in which Y represents N can likewise be reacted in a sequence of acylation with a suitable acylating agent (for example acetic anhydride for R A = methyl), oxidation with an appropriate oxidizing agent (for example 2,3-dichloro-5,6-dicyano-l,4-benzoquinone) and removal of the acyl group by suitable methods (for example heating in hydrochloric acid, cf. Greene 's protective groups in organic synthesis, 4th ed., P.G.M. Wuts, T.W. Greene, John Wiley & Sons, Inc., Hoboken, New Jersey, 2007), to give lH-pyrazole-3 -amines of the formula (II-l). Access to lH-pyrazole-3 -amines of the formula (II-l) is also provided via route E-1 starting with keto compounds of the formula (1-8) substituted with a leaving group LG 3/4 (for example LG 3/4 = OR where R = alkyl, acyl, sulphonyl, etc.; LG 3/4 = SR where R = alkyl, acyl, etc.; LG 3/4 = NHR or NR 2 where R = hydrogen, alkyl, acyl, sulphonyl; LG 3/4 = halogen). These are initially activated with ammonia via β- enaminoketones (LG 3 = NH2/LG 4 = alkoxy) (cf. M. A. P. Martins, W. Cunico, S. Brondani, R. L. Peres, N. Zimmermann, F. A. Rosa, G. F. Fiss, N. Zanatta, H. G. Bonacorso Synthesis 2006, 1485) and then, in the presence of suitable bases (for example triethylamine) reacted with free hydrazines or salts thereof (for example hydrochlorides) to give lH-pyrazole-3 -amines of the formula (II-l). lH-Pyrazole-3 -amines of the formula (II-l) can optionally be halogenated via route F-l if R3 represents H (hydrogen), using suitable halogenating agents (for example N-halosuccinimides) in the 3-position to give compounds of the formula (1-8) in which R3 represents chlorine, bromine or iodine (cf. J. Velcicky, R. Feifel, S. Hawtin, R. Heng, C. Huppertz, G. Koch, M. Kroemer, H. Moebitz, L. Revesz, C. Scheufler, A. Schlapbach Bioorg. Med. Chem. Letters 2010, 20, 1293). Amines of the formula (II-2)

are likewise commercially available.

The amines of the formula (II-2) can be obtained according to Synthesis Scheme 3

Synthesis Scheme 3

Via route A-3, aromatic hydrazines of the formula (3-1) can be reacted, for example, with a nitrosoketone (for example nitrosoacetone for R3=H, cf. M. Begtrup, J. Holm J. Chem. Soc, Perkin Trans. 1, 1981, 503) and then cyclized with the aid of condensing agents (for example acetic anhydride, cf. D. L. Swartz, A. R. Karash, L. A. Berry, D. L. Jaeger J. Heterocyclic Chem. 1983, 20, 1561) to give 2H-l,2,3-triazoles of the formula (3-3). Oxidation (for example with sodium chromate(VI) cf. Comprehensive Organic Transformations: A Guide to Functional Group Preparations; Larock, R. C, Ed.; Wiley- VCH: New York, 1999) of (3-3) affords the carboxylic acid (3-4) which can then be converted by Curtius degradation into the 4-amino-2H-l,2,3-triazole (Π-2) (cf. P. A. S. Smith Org. React. 1946, 337).

Alternatively, route B-3 can also be followed for preparing the 4-amino-2H-l,2,3-triazoles (Π-2) (cf. V. M. Nikitin, A. V. Zavodov, L. I. Vereshchagin Zhurnal Organicheskoi Khimii 1992, 28, 2334). To this end, an aromatic amine (3-5) is diazotized and the diazonium salt (3-6) is reacted, for example, with metazonic acid (for R3=H). The resulting 4-nitro-2H-l,2,3-triazole (3-7) can then be reduced with, for example, tin(II) chloride to give 4-amino-2H-l,2,3-triazole (Π-2).

Amines of the formula (II-3)

can be obtained via Synthesis Scheme 4.

Synthesis Scheme 4

To this end, aromatic amines of the formula (4-1) are reacted, for example, with cyclic acetals of the formula (4-2) under acidic conditions to give the pyrrole (4-3) (for example FeCl 3 cf. N. Azizi, A. Khajeh-Amiria, H. Ghafurib, M. Bolourtchiana, M. R. Saidi Synlett 2009, 14, 2245). Nitration of the pyrrole (4-3) to 3-nitro-lH-pyrrole (4-4) (for example with acetyl nitrate, cf. D. Korakas, G. Varvounis J. Heterocyclic Chem. 1996, 33, 611) and subsequent reduction (for example with SnCl 2 , cf. WO 2009/136995) affords the 3-amino-lH-pyrrole (II-3).

Amines of the formula (II-5)

are likewise commercially available. Novel lH-Indazole-3 -amines of the formula (II-5) can be obtained according to Synthesis Scheme 2. Synthesis Scheme 2

Here, compounds of the formula (2-1) are reacted via route A-2 with aromatics or heteroaromatics of the formula (2-2) substituted by a suitable leaving group LG, to react in the presence of a base (for example sodium hydride for, for instance, LG = chlorine (cf.WO 2008/068171)) and optionally a catalyst (for example CuI/N,N-dimethylethane-l,2-diamine, potassium carbonate for, for instance, LG = bromine (cf. WO 2010/098367) or Pd2(dba)3/X-Phos, caesium carbonate for, for instance, LG = chlorine (cf. DE 10 2009/004245)) to give compounds of the formula (Π-5). 1 H-Indazole-3 -amines of the formula (2-1) and aromatics or heteroaromatics of the formula (2-2) are commercially available or can be obtained by known processes.

Via route B-2, it is alternatively possible to convert ortho-halobenzonitriles of the formula (2-3) with hydrazides of the formula (2-4) in the presence of a catalyst and a base (for example copper(I) bromide/4-hydroxy-L-proline; potassium carbonate for X=Br or I and Ar=phenyl, cf. L. Xu, Y. Peng, Q. Pan, Y. Jiang, D. Ma J. Org. Chem. 2013, 78, 3400) to give lH-indazole-3 -amines of the formula (II-5). The processes according to the invention for preparation of the novel compounds of the formula (I) are preferably performed using a diluent. Useful diluents for performance of the processes according to the invention are, as well as water, all inert solvents. Examples include: halohydrocarbons (for example chlorohydrocarbons such as tetrachloroethylene, tetrachloroethane, dichloropropane, methylene chloride, dichlorobutane, chloroform, carbon tetrachloride, trichloroethane, trichloroethylene, pentachloroethane, difluorobenzene, 1 ,2-dichloroethane, chlorobenzene, bromobenzene, dichlorobenzene, chlorotoluene, trichlorobenzene), alcohols (for example methanol, ethanol, isopropanol, butanol), ethers (for example ethyl propyl ether, methyl tert-butyl ether, anisole, phenetole, cyclohexyl methyl ether, dimethyl ether, diethyl ether, dipropyl ether, diisopropyl ether, di-n-butyl ether, diisobutyl ether, diisoamyl ether, ethylene glycol dimethyl ether, tetrahydrofuran, 1,4-dioxane, dichlorodiethyl ether and polyethers of ethylene oxide and/or propylene oxide), amines (for example trimethyl-, triethyl-, tripropyl-, tributylamine, N-methylmorpholine, pyridine and tetramethylenediamine), nitrohydrocarbons (for example nitromethane, nitroethane, nitropropane, nitrobenzene, chloronitrobenzene, o-nitrotoluene); nitriles (for example acetonitrile, propionitrile, butyronitrile, isobutyronitrile, benzonitrile, m-chlorobenzonitrile), tetrahydrothiophene dioxide, dimethyl sulphoxide, tetramethylene sulphoxide, dipropyl sulphoxide, benzyl methyl sulphoxide, diisobutyl sulphoxide, dibutyl sulphoxide, diisoamyl sulphoxide, sulphones (for example dimethyl, diethyl, dipropyl, dibutyl, diphenyl, dihexyl, methyl ethyl, ethyl propyl, ethyl isobutyl and pentamethylene sulphone), aliphatic, cycloaliphatic or aromatic hydrocarbons (for example pentane, hexane, heptane, octane, nonane and technical hydrocarbons), and also what are called "white spirits" with components having boiling points in the range from, for example, 40°C to 250°C, cymene, petroleum fractions within a boiling range from 70°C to 190°C, cyclohexane, methylcyclohexane, petroleum ether, ligroin, benzene, toluene, xylene, esters (for example methyl, ethyl, butyl and isobutyl acetate, dimethyl, dibutyl and ethylene carbonate); amides (for example hexamethylphosphoric triamide, formamide, N-methylformamide, NN-dimethylformamide, NN-dipropylformamide, NN- dibutylformamide, N-methylpyrrolidine, N-methylcaprolactam, l,3-dimethyl-3,4,5,6-tetrahydro-2(lH)- pyrimidine, octylpyrrolidone, octylcaprolactam, l,3-dimethyl-2-imidazolinedione, N-formylpiperidine, NN'-diformylpiperazine) and ketones (for example acetone, acetophenone, methyl ethyl ketone, methyl butyl ketone).

It is of course also possible to perform the process according to the invention in mixtures of the solvents and diluents mentioned.

When performing the process according to the invention, the reaction temperatures can be varied within a relatively wide range. In general, the temperatures employed are between -30°C and +150°C, preferably between -10°C and +100 °C.

The process according to the invention is generally performed under atmospheric pressure. However, it is also possible to perform the process according to the invention under elevated or reduced pressure - generally at absolute pressures between 0.1 bar and 15 bar.

To perform the process according to the invention, the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a relatively large excess. The reaction is generally carried out in a suitable diluent in the presence of a reaction auxiliary, optionally also under a protective gas atmosphere (for example under nitrogen, argon or helium) and the reaction mixture is generally stirred at the temperature required for several hours. The workup is performed by customary methods (cf. the Preparation Examples). The basic reaction auxiliaries used to perform the process according to the invention may be all suitable acid binders. Examples include: alkaline earth metal or alkali metal compounds (e.g. hydroxides, hydrides, oxides and carbonates of lithium, sodium, potassium, magnesium, calcium and barium), amidine bases or guanidine bases (e.g. 7-methyl-l,5,7-triazabicyclo[4.4.0]dec-5-ene (MTBD); diazabicyclo[4.3.0]nonene (DBN), diazabicyclo[2.2.2]octane (DABCO), 1,8- diazabicyclo[5.4.0]undecene (DBU), cyclohexyltetrabutylguanidine (CyTBG), cyclohexyltetramethylguanidine (CyTMG), N,N,N,N-tetramethyl-l,8-naphthalenediamine, pentamethylpiperidine) and amines, especially tertiary amines (e.g. triethylamine, trimethylamine, tribenzylamine, triisopropylamine, tributylamine, tricyclohexylamine, triamylamine, trihexylamine, N,N-dimethylaniline, Ν,Ν-dimethyltoluidine, N,N-dimethyl-p-aminopyridine, N-methylpyrrolidine, N- methylpiperidine, N-methylimidazole, N-methylpyrazole, N-methylmorpholine, N- methylhexamethylenediamine, pyridine, 4-pyrrolidinopyridine, 4-dimethylaminopyridine, quinoline, 2- picoline, 3-picoline, pyrimidine, acridine, N,N,N` ,N`-ttetramethnyeldiamine, Ν,Ν,Ν',Ν'- tetraethylenediamine, quinoxaline, N-propyldiisopropylamine, N-ethyldiisopropylamine, Ν,Ν'- dimethylcyclohexylamine, 2,6-lutidine, 2,4-lutidine or triethylenediamine). The acidic reaction auxiliaries used to perform the process according to the invention include all mineral acids (e.g. hydrohalic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid or hydriodic acid, and also sulphuric acid, phosphoric acid, phosphorous acid, nitric acid), Lewis acids (e.g. aluminium(III) chloride, boron trifluoride or its etherate, titanium(IV) chloride, tin(IV) chloride) and organic acids (e.g. formic acid, acetic acid, propionic acid, malonic acid, lactic acid, oxalic acid, fumaric acid, adipic acid, stearic acid, tartaric acid, oleic acid, methanesulphonic acid, benzoic acid, benzenesulphonic acid or para-toluenesulphonic acid).

Definitions

In the context of the present invention "harmful microorganisms" are phytopathogenic fungi, phytopathogenic bacteria, phytopathogenic oomycetes, and phytopathogenic viruses. "Phytopathogenic" means that the respective organism is capable of infesting plants or plant parts.

In the context of the present invention, "control of harmful microorganisms" means a reduction in infestation by harmful microorganisms, compared with the untreated plant or plant part as defined below measured as fungicidal efficacy, preferably a reduction by 25-50 %, compared with the untreated plant (100 %), more preferably a reduction by 40-79 %, compared with the untreated plant (100 %); even more preferably, the infection by harmful microorganisms is entirely suppressed (by 70-100 %). The control may be curative, i.e. for treatment of already infected plants, or protective, for protection of plants which have not yet been infected.

An "effective but non-phytotoxic amount" means an amount of the compounds according to formula (I) which is sufficient to control the fungal disease of the plant in a satisfactory manner or to eradicate the fungal disease completely, and which, at the same time, does not cause any significant symptoms of phytotoxicity. In general, this application rate may vary within a relatively wide range. It depends on several factors, for example on the fungus to be controlled, the plant, the climatic conditions and the ingredients of the inventive compositions. Formulations

The present invention further relates to formulations and use forms prepared therefrom as compositions controlling unwanted microorganisms, for example drench, drip and spray liquors, comprising at least one compound of the formula (I). In some cases, the use forms comprise further fungicides and/or adjuvants which improve action, such as penetrants, e.g. vegetable oils, for example rapeseed oil, sunflower oil, mineral oils, for example paraffin oils, alkyl esters of vegetable fatty acids, for example rapeseed oil methyl ester or soya oil methyl ester, or alkanol alkoxylates and/or spreaders, for example alkylsiloxanes and/or salts, for example organic or inorganic ammonium or phosphonium salts, for example ammonium sulphate or diammonium hydrogenphosphate and/or retention promoters, for example dioctyl sulphosuccinate or hydroxypropyl guar polymers and/or humectants, for example glycerol and/or fertilizers, for example ammonium-, potassium- or phosphorus-containing fertilizers.

Customary formulations are, for example, water-soluble liquids (SL), emulsion concentrates (EC), emulsions in water (EW), suspension concentrates (SC, SE, FS, OD), water-dispersible granules (WG), granules (GR) and capsule concentrates (CS); these and further possible formulation types are described, for example, by Crop Life International and in Pesticide Specifications, Manual on development and use of FAO and WHO specifications for pesticides, FAO Plant Production and Protection Papers - 173, prepared by the FAO/WHO Joint Meeting on Pesticide Specifications, 2004, ISBN: 9251048576. The formulations, in addition to one or more compounds of the formula (I), optionally comprise further agrochemically active compounds.

These are preferably formulations or use forms which comprise auxiliaries, for example extenders, solvents, spontaneity promoters, carriers, emulsifiers, dispersants, frost protectants, biocides, thickeners and/or further auxiliaries, for example adjuvants. An adjuvant in this context is a component which enhances the biological effect of the formulation, without the component itself having any biological effect. Examples of adjuvants are agents which promote retention, spreading, attachment to the leaf surface or penetration. These formulations are prepared in a known way, for example by mixing the compounds of the formula (I) with auxiliaries such as, for example, extenders, solvents and/or solid carriers and/or other auxiliaries such as, for example, surfactants. The formulations are prepared either in suitable facilities or else before or during application. The auxiliaries used may be substances suitable for imparting special properties, such as certain physical, technical and/or biological properties, to the formulation of the compounds of the formula (I), or to the use forms prepared from these formulations (for example ready-to-use fungicides such as spray liquors or seed dressing products).

Suitable extenders are, for example, water, polar and nonpolar organic chemical liquids, for example from the classes of the aromatic and non-aromatic hydrocarbons (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), the alcohols and polyols (which, if appropriate, may also be substituted, etherified and/or esterified), the ketones (such as acetone, cyclohexanone), esters (including fats and oils) and (poly)ethers, the unsubstituted and substituted amines, amides, lactams (such as N- alkylpyrrolidones) and lactones, the sulphones and sulphoxides (such as dimethyl sulphoxide). If the extender used is water, it is also possible to employ, for example, organic solvents as auxiliary solvents. Essentially, suitable liquid solvents are: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example mineral oil fractions, mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulphoxide, and also water.

In principle, it is possible to use all suitable solvents. Examples of suitable solvents are aromatic hydrocarbons, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic or chlorinated aliphatic hydrocarbons, such as chlorobenzene, chloroethylene or methylene chloride, aliphatic hydrocarbons, such as cyclohexane, paraffins, petroleum fractions, mineral and vegetable oils, alcohols, such as methanol, ethanol, isopropanol, butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethyl sulphoxide, and also water. In principle, it is possible to use all suitable carriers. Useful carriers include especially: for example ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic materials such as finely divided silica, alumina and natural or synthetic silicates, resins, waxes and/or solid fertilizers. Mixtures of such carriers can likewise be used. Useful carriers for granules include: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite, and synthetic granules of inorganic and organic meals, and also granules of organic material such as sawdust, paper, coconut shells, corn cobs and tobacco stalks.

Liquefied gaseous extenders or solvents can also be used. Particularly suitable extenders or carriers are those which are gaseous at ambient temperature and under atmospheric pressure, for example aerosol propellant gases, such as halohydrocarbons, and also butane, propane, nitrogen and carbon dioxide.

Examples of emulsifiers and/or foam- formers, dispersants or wetting agents with ionic or nonionic properties, or mixtures of these surfactants, are salts of polyacrylic acid, salts of lignosulphonic acid, salts of phenolsulphonic acid or naphthalenesulphonic acid, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, with substituted phenols (preferably alkylphenols or arylphenols), salts of sulphosuccinic esters, taurine derivatives (preferably alkyl taurates), phosphoric esters of polyethoxylated alcohols or phenols, fatty esters of polyols, and derivatives of the compounds containing sulphates, sulphonates and phosphates, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates, protein hydrolysates, lignosulphite waste liquors and methylcellulose. The presence of a surfactant is advantageous if one of the compounds of the formula (I) and/or one of the inert carriers is insoluble in water and when the application takes place in water.

It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and nutrients and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc as further auxiliaries in the formulations and the use forms derived therefrom.

Additional components may be stabilizers, such as low-temperature stabilizers, preservatives, antioxidants, light stabilizers or other agents which improve chemical and/or physical stability. Foam formers or antifoams may also be present.

Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or else natural phospholipids such as cephalins and lecithins and synthetic phospholipids may also be present as additional auxiliaries in the formulations and the use forms derived therefrom. Further possible auxiliaries are mineral and vegetable oils.

Optionally, further auxiliaries may be present in the formulations and the use forms derived therefrom. Examples of such additives include fragrances, protective colloids, binders, adhesives, thickeners, thixotropic agents, penetrants, retention promoters, stabilizers, sequestrants, complexing agents, humectants, spreaders. In general, the compounds of the formula (I) can be combined with any solid or liquid additive commonly used for formulation purposes. Useful retention promoters include all those substances which reduce the dynamic surface tension, for example dioctyl sulphosuccinate, or increase the viscoelasticity, for example hydroxypropylguar polymers.

Suitable penetrants in the present context are all those substances which are usually used for improving the penetration of agrochemical active compounds into plants. Penetrants are defined in this context by their ability to penetrate from the (generally aqueous) application liquor and/or from the spray coating into the cuticle of the plant and thereby increase the mobility of active compounds in the cuticle. The method described in the literature (Baur et al., 1997, Pesticide Science 51, 131-152) can be used to determine this property. Examples include alcohol alkoxylates such as coconut fatty ethoxylate (10) or isotridecyl ethoxylate (12), fatty acid esters, for example rapeseed oil methyl ester or soya oil methyl ester, fatty amine alkoxylates, for example tallowamine ethoxylate (15), or ammonium and/or phosphonium salts, for example ammonium sulphate or diammonium hydrogenphosphate.

The formulations preferably comprise between 0.00000001 and 98% by weight of the compound of the formula (I) or, with particular preference, between 0.01% and 95%> by weight of the compound of the formula (I), more preferably between 0.5%> and 90%> by weight of the compound of the formula (I), based on the weight of the formulation.

The content of the compound of the formula (I) in the use forms prepared from the formulations (in particular fungicides) may vary within wide ranges. The concentration of the compound of the formula (I) in the use forms is usually between 0.00000001 and 95%> by weight of the compound of the formula (I), preferably between 0.00001 and 1%> by weight, based on the weight of the use form. The compounds are employed in a customary manner appropriate for the use forms.

Plant/Crop Protection

The compounds according to the invention have potent microbicidal activity and can be used for control of harmful microorganisms, such as fungi and bacteria, in crop protection and in the protection of materials.

The invention also relates to a method for controlling harmful microorganisms, characterized in that the compounds according to the invention are applied to the harmful microorganims and/or their habitat.

The compounds according to the invention can be used in crop protection for control of phytopathogenic fungi. They are characterized by an outstanding efficacy against a broad spectrum of phytopathogenic fungi, including soilborne pathogens, which are in particular members of the classes Plasmodiophoromycetes, Peronosporomycetes (Syn. Oomycetes), Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes (Syn. Fungi imperfecti). Some fungicides are systemically active and ca be used in plant protection as foliar, seed dressing or soil fungicide. Furthermore, they are suitable for controlling fungi, which inter alia infest wood or roots of plant.

The compounds according to the invention can be used in crop protection for control of phytopathogenic bacteria. They are characterized by an outstanding efficacy against a broad spectrum of phytopathogenic bacteria, including Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.

Non-limiting examples of pathogens of fungal diseases which can be treated in accordance with the invention include: diseases caused by powdery mildew pathogens, for example Blumeria species, for example Blumeria graminis; Podosphaera species, for example Podosphaera leucotricha; Sphaerotheca species, for example Sphaerotheca fuliginea; Uncinula species, for example Uncinula necator; diseases caused by rust disease pathogens, for example Gymnosporangium species, for example Gymnosporangium sabinae; Hemileia species, for example Hemileia vastatrix; Phakopsora species, for example Phakopsora pachyrhizi and Phakopsora meibomiae; Puccinia species, for example Puccinia recondite, P. triticina, P. graminis or P. striiformis; Uromyces species, for example Uromyces appendiculatus; diseases caused by pathogens from the group of the Oomycetes, for example Albugo species, for example Algubo Candida; Bremia species, for example Bremia lactucae; Peronospora species, for example Peronospora pisi or P. brassicae; Phytophthora species, for example Phytophthora infestans; Plasmopara species, for example Plasmopara viticola; Pseudoperonospora species, for example Pseudoperonospora humuli or Pseudoperonospora cubensis; Pythium species, for example Pythium ultimum; leaf blotch diseases and leaf wilt diseases caused, for example, by Alternaria species, for example Alternaria solani; Cercospora species, for example Cercospora beticola; Cladiosporium species, for example Cladiosporium cucumerinum; Cochliobolus species, for example Cochliobolus sativus (conidia form: Drechslera, Syn: Helminthosporium), Cochliobolus miyabeanus; Colletotrichum species, for example Colletotrichum lindemuthanium; Cycloconium species, for example Cycloconium oleaginum; Diaporthe species, for example Diaporthe cirri; Elsinoe species, for example Elsinoe fawcettii; Gloeosporium species, for example Gloeosporium laeticolor; Glomerella species, for example Glomerella cingulata; Guignardia species, for example Guignardia bidwelli; Leptosphaeria species, for example Leptosphaeria maculans, Leptosphaeria nodorum; Magnaporthe species, for example Magnaporthe grisea; Microdochium species, for example Microdochium nivale; Mycosphaerella species, for example Mycosphaerella graminicola, M. arachidicola and M. fijiensis; Phaeosphaeria species, for example Phaeosphaeria nodorum; Pyrenophora species, for example Pyrenophora teres, Pyrenophora tritici repentis; Ramularia species, for example Ramularia collo-cygni, Ramularia areola; Rhynchosporium species, for example Rhynchosporium secalis; Septoria species, for example Septoria apii, Septoria lycopersii; Typhula species, for example Typhula incarnata; Venturia species, for example Venturia inaequalis; root and stem diseases caused, for example, by Corticium species, for example Corticium graminearum; Fusarium species, for example Fusarium oxysporum; Gaeumannomyces species, for example Gaeumannomyces graminis; Rhizoctonia species, such as, for example Rhizoctonia solani; Sarocladium diseases caused for example by Sarocladium oryzae; Sclerotium diseases caused for example by Sclerotium oryzae; Tapesia species, for example Tapesia acuformis; Thielaviopsis species, for example Thielaviopsis basicola; ear and panicle diseases (including corn cobs) caused, for example, by Alternaria species, for example Alternaria spp.; Aspergillus species, for example Aspergillus flavus; Cladosporium species, for example Cladosporium cladosporioides; Claviceps species, for example Claviceps purpurea; Fusarium species, for example Fusarium culmorum; Gibberella species, for example Gibberella zeae; Monographella species, for example Monographella nivalis; Septoria species, for example Septoria nodorum; diseases caused by smut fungi, for example Sphacelotheca species, for example Sphacelotheca reiliana; Tilletia species, for example Tilletia caries, T. controversa; Urocystis species, for example Urocystis occulta; Ustilago species, for example Ustilago nuda, U. nuda tritici; fruit rot caused, for example, by Aspergillus species, for example Aspergillus flavus; Botrytis species, for example Botrytis cinerea; Penicillium species, for example Penicillium expansum and P. purpurogenum; Sclerotinia species, for example Sclerotinia sclerotiorum; Verticilium species, for example Verticilium alboatrum; seed and soilborne decay, mould, wilt, rot and damping-off diseases caused, for example, by Alternaria species, caused for example by Alternaria brassicicola; Aphanomyces species, caused for example by Aphanomyces euteiches; Ascochyta species, caused for example by Ascochyta lentis; Aspergillus species, caused for example by Aspergillus flavus; Cladosporium species, caused for example by Cladosporium herbarum; Cochliobolus species, caused for example by Cochliobolus sativus; (Conidiaform: Drechslera, Bipolaris Syn: Helminthosporium); Colletotrichum species, caused for example by Colletotrichum coccodes; Fusarium species, caused for example by Fusarium culmorum; Gibberella species, caused for example by Gibberella zeae; Macrophomina species, caused for example by Macrophomina phaseolina; Monographella species, caused for example by Monographella nivalis; Penicillium species, caused for example by Penicillium expansum; Phoma species, caused for example by Phoma lingam; Phomopsis species, caused for example by Phomopsis sojae; Phytophthora species, caused for example by Phytophthora cactorum; Pyrenophora species, caused for example by Pyrenophora graminea; Pyricularia species, caused for example by Pyricularia oryzae; Pythium species, caused for example by Pythium ultimum; Rhizoctonia species, caused for example by Rhizoctonia solani; Rhizopus species, caused for example by Rhizopus oryzae; Sclerotium species, caused for example by Sclerotium rolfsii; Septoria species, caused for example by Septoria nodorum; Typhula species, caused for example by Typhula incarnata; Verticillium species, caused for example by Verticillium dahliae; cancers, galls and witches' broom caused, for example, by Nectria species, for example Nectria galligena; wilt diseases caused, for example, by Monilinia species, for example Monilinia laxa; leaf blister or leaf curl diseases caused, for example, by Exobasidium species, for example Exobasidium vexans;

Taphrina species, for example Taphrina deformans; decline diseases of wooden plants caused, for example, by Esca disease, caused for example by Phaemoniella clamydospora, Phaeoacremonium aleophilum and Fomitiporia mediterranea; Eutypa dyeback, caused for example by Eutypa lata ; Ganoderma diseases caused for example by Ganoderma boninense; Rigidoporus diseases caused for example by Rigidoporus lignosus; diseases of flowers and seeds caused, for example, by Botrytis species, for example Botrytis cinerea; diseases of plant tubers caused, for example, by Rhizoctonia species, for example Rhizoctonia solani; Helminthosporium species, for example Helminthosporium solani; Club root caused, for example, by Plasmodiophora species, for example Plamodiophora brassicae; diseases caused by bacterial pathogens, for example Xanthomonas species, for example Xanthomonas cam-pestris pv. oryzae; Pseudomonas species, for example Pseudomonas syringae pv. lachrymans; Erwinia species, for example Erwinia amylovora.

The following diseases of soya beans can be controlled with preference: Fungal diseases on leaves, stems, pods and seeds caused, for example, by Alternaria leaf spot (Alternaria spec, atrans tenuissima), Anthracnose (Colletotrichum gloeosporoides dematium var. truncatum), brown spot (Septoria glycines), cercospora leaf spot and blight (Cercospora kikuchii), choanephora leaf blight (Choanephora infundibulifera trispora (Syn.)), dactuliophora leaf spot (Dactuliophora glycines), downy mildew (Peronospora manshurica), drechslera blight (Drechslera glycini), frogeye leaf spot (Cercospora sojina), leptosphaerulina leaf spot (Leptosphaerulina trifolii), phyllostica leaf spot (Phyllosticta sojaecola), pod and stem blight (Phomopsis sojae), powdery mildew (Microsphaera diffusa), pyrenochaeta leaf spot (Pyrenochaeta glycines), rhizoctonia aerial, foliage, and web blight (Rhizoctonia solani), rust (Phakopsora pachyrhizi, Phakopsora meibomiae), scab (Sphaceloma glycines), stemphylium leaf blight (Stemphylium botryosum), target spot (Corynespora cassiicola).

Fungal diseases on roots and the stem base caused, for example, by black root rot (Calonectria crotalariae), charcoal rot (Macrophomina phaseolina), fusarium blight or wilt, root rot, and pod and collar rot (Fusarium oxysporum, Fusarium orthoceras, Fusarium semitectum, Fusarium equiseti), mycoleptodiscus root rot (Mycoleptodiscus terrestris), neocosmospora (Neocosmospora vasinfecta), pod and stem blight (Diaporthe phaseolorum), stem canker (Diaporthe phaseolorum var. caulivora), phytophthora rot (Phytophthora megasperma), brown stem rot (Phialophora gregata), pythium rot (Pythium aphanidermatum, Pythium irregulare, Pythium debaryanum, Pythium myriotylum, Pythium ultimum), rhizoctonia root rot, stem decay, and damping-off (Rhizoctonia solani), sclerotinia stem decay (Sclerotinia sclerotiorum), sclerotinia southern blight (Sclerotinia rolfsii), thielaviopsis root rot (Thielaviopsis basicola).

The compounds according to the invention, compositions comprising these compounds are suitable for controlling the following plant diseases:

Albugo spp. (white rust) on ornamental plants, vegetable crops (e.g. A. Candida) and sunflowers (e.g. A. tragopogonis); Alternaria spp. (black spot disease, black blotch) on vegetables, oilseed rape (e.g. A. brassicola or A. brassicae), sugar beet (e.g. A. tenuis), fruit, rice, soybeans and also on potatoes (e.g. A. solani or A. alternata) and tomatoes (e.g. A. solani or A. alternata) and Alternaria spp. (black head) on wheat; Aphanomyces spp. on sugar beet and vegetables; Ascochyta spp. on cereals and vegetables, e.g. A. tritici (Ascochyta leaf blight) on wheat and A. hordei on barley; Bipolaris and Drechslera spp. (teleomorph: Cochliobolus spp.), e.g. leaf spot diseases (D. maydis and B. zeicola) on corn, e.g. glume blotch (B. sorokiniana) on cereals and e.g. B. oryzae on rice and on lawn; Blumeria (old name: Erysiphe) graminis (powdery mildew) on cereals (e.g. wheat or barley); Botryo-'sphaeria spp. ('Slack Dead Arm Disease') on grapevines (e.g. B. obtusa); Botrytis cinerea (teleomorph: Botryotinia fuckeliana: gray mold, gray rot) on soft fruit and pomaceous fruit (inter alia strawberries), vegetables (inter alia lettuce, carrots, celeriac and cabbage), oilseed rape, flowers, grapevines, forest crops and wheat (ear mold); Bremia lactucae (downy mildew) on lettuce; Ceratocystis (syn. Ophiostoma) spp. (blue stain fungus) on deciduous trees and coniferous trees, e.g. C. ulmi (Dutch elm disease) on elms; Cercospora spp. (Cereospora leat spot) on corn (e.g. C. zeae-maydis), rice, sugar beet (e.g. C. beticola), sugar cane, vegetables, coffee, soybeans (e.g. C. sojina or C. kikuchil) and rice; Cladosporium spp. on tomato (e.g. C. fulvum: tomato leaf mold) and cereals, e.g. C. herbarum (ear rot) on wheat; Claviceps purpurea (ergot) on cereals; Cochliobolus (anamorph: Helminthosporium or Bipolaris) spp. (leaf spot) on corn (e.g. C. carbonum), cereals (e.g. C. sativus, anamorph: B. sorokiniana: glume blotch) and rice (tor example C. miyabeanus, anamorph: H. oryzae); Colletotrichum(teleomorph: Glomerella) spp. (anthracnosis) on cotton (e.g. C. gossypii), corn (e.g. C. graminicola: stem rot and anthracnosis), soft fruit, potatoes (e.g. C. coccodes: wilt disease), beans (e.g. C. lindemuthianum) and soybeans (e.g. C. truncatum); Corticium spp., e.g. C. sasakii (sheath blight) on rice; Corynespora cassiicola (leaf spot) on soybeans and ornamental plants; Cycloconium spp., e.g. C. oleaginum on olives; Cylindrocarpon spp. (e.g. fruit tree cancer or black foot disease of grapevine, teleomorph: Nectria or Neonectria spp.) on fruit trees, grapevines (e.g. C. liriodendn; teleomorph: Neonectria liriodendri, black foot disease) and many ornamental trees; Dematophora (teleomorph: Rosellinia) necatrix (root/stem rot) on soybeans; Diaporthe spp. e.g. D. phaseolorum (stem disease) on soybeans; Drechslera (syn. Helminthosporium, teleomorph: Pyrenophora) spp. on corn, cereals, such as barley (e.g. D. teres, net blotch) and on wheat (e.g. D. tritici- repentis: DTR leaf spot), rice and lawn; Esca disease (dieback of grapevine, apoplexia) on grapevines, caused by Formitiporia (syn. Phellinus) punctata, F mediterranea. Phaeomoniella chlamydospora (old name Phaeoacremonium chlamydosporum) , Phaeoacremonium aleophilum and/or Botryosphaeria obtusa; Elsinoe spp. on pome fruit (E. pyri) and soft fruit (E. veneta: anthracnosis) and also grapevines (E. ampelina: anthracnosis); Entyloma oryzae (leaf smut) on rice; Epicoccum spp. (black head) on wheat; Erysiphe spp. (powdery mildew) on sugar beet (E. betae), vegetables (e.g. E. pisi), such as cucumber species (e.g. E. cichoracearum) and cabbage species, such as oilseed rape (e.g. E. cruciferarum); Eutypa fata (Eutypa cancer or dieback, anamorph: Cytosporina lata, syn. Libertella blepharis) on fruit trees, grapevines and many ornamental trees; Exserohilum (syn. Helminthosporium) spp. on corn (e.g. E. turcicum); Fusarium (teleomorph: Gibberella) spp. (wilt disease, root and stem rot) on various plants, such as e.g. F. graminearum or F. culmorum (root rot and silver-top) on cereals (e.g. wheat or barley), F. oxysporum on tomatoes, F. solani on soybeans and F. verticillioides on corn; Gaeumannomyces graminis (takeall) on cereals (e.g. wheat or barley) and corn; Gibberella spp. on cereals (e.g. G. zeae) and rice (e.g. G. fujikuroi: bakanae disease); Glomerella cingulata on grapevines, pomaceous fruit and other plants and G. gossypii on cotton; grainstaining complex on rice; Guignardia bidwellii (black rot) on grapevines; Gymno-sporangium spp. on Rosaceae and juniper, e.g. G. sabinae (pear rust) on pears; Helminthosporium spp. (syn. Drechslera, teleomorph: Cochliobolus) on corn, cereals and rice; Hemileia spp., e.g. H. vastatrix (coffee leaf rust) on coffee; Isariopsis clavispora (syn. Cladosporium vitis) on grapevines; Macrophomina phaseolina (syn. phaseoli) (root/stem rot) on soybeans and cotton; Microdochium (syn. Fusarium) nivale (pink snow mold) on cereals (e.g. wheat or barley); Microsphaera diffusa (powdery mildew) on soybeans; Monilinia spp., e.g. M. laxa. M. fructicola and M. fructigena (blossom and twig blight) on stone fruit and other Rosaceae; Mycosphaerella spp. on cereals, bananas, soft fruit and peanuts, such as e.g. M. graminicola (anamorph: Septoria tritici, Septoria leaf blotch) on wheat or M. fijiensis (Sigatoka disease) on bananas; Peronospora spp. (downy mildew) on cabbage (e.g. P. brassicae), oilseed rape (e.g. P. parasitica), bulbous plants (e.g. P. destructor), tobacco (P. tabacina) and soybeans (e.g. P. manshurica); Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybeans; Phialophora spp. e.g. on grapevines (e.g. P. tracheiphila and P. tetraspora) and soybeans (e.g. P. gregata: stem disease); Phoma lingam (root and stem rot) on oilseed rape and cabbage and P. betae (leaf spot) on sugar beet; Phomopsis spp. on sunflowers, grapevines (e.g. P. viticola: dead-arm disease) and soybeans (e.g. stem canker/stem blight: P. phaseoli, teleomorph: Diaporthe phaseolorum); Physoderma maydis (brown spot) on corn; Phytophthora spp. (wilt disease, root, leaf, stem and fruit rot) on various plants, such as on bell peppers and cucumber species (e.g. P. capsici), soybeans (e.g. P. megasperma, syn. P. sojae), potatoes and tomatoes (e.g. P. infestans. late blight and brown rot) and deciduous trees (e.g. P. ramorum sudden oak death); Plasmodiophora brassicae (club-root) on cabbage, oilseed rape, radish and other plants; Plasmopara spp., e.g. P. viticola (peronospora of grapevines, downy mildew) on grapevines and P. halstedii on sunflowers; Podosphaera spp. (powdery mildew) on Rosaceae, hops, pomaceaus fruit and soft fruit, e.g. P. leucotricha on apple; Polymyxa spp., e.g. on cereals, such as barley and wheat (P. graminis) and sugar beet (P. betae) and the viral diseases transmitted thereby; Pseudocercosporella herpotrichoides (eyespot/stem break, teleomorph: Tapesia yallundae) on cereals, e.g. wheat or barley; Pseudoperonospora (downy mildew) on various plants, e.g. P. cubensis on cucumber species or P. humili on hops; Pseudopezicula tracheiphila (angular leaf scorch, anamorph Phialophora) on grapevines; Puccinia spp. (rust disease) on various plants, e.g. P. triticina (brown rust of wheat), P. striiformis (yellow rust). P. hordei (dwarf leaf rust), P. graminis (black rust) or P. recondita (brown rust of rye) on cereals, such as e.g. wheat, barley or rye. P. kuehnii on sugar cane and, e.g., on asparagus (e.g. P. asparagi); Pyrenophora (anamorph: Drechslera) tritici-repentis (speckled leaf blotch) on wheat or P. teres (net blotch) on barley; Pyricularia spp., e.g. P. oryzae (teleomorph: Magnaporthe grisea. rice blast) on rice and P. grisea on lawn and cereals; Pythium spp. (damping-off disease) on lawn, rice, corn, wheat, cotton, oilseed rape, sunflowers, sugar beet, vegetables and other plants (e.g. P. ultimum or P. aphanidermatum); Ramularia spp., e.g. R. collo- cygni(Ramularia leaf and lawn spot/physiological leaf spot) on barley and R. beticola on sugar beet; Rhizoctonia spp. on cotton, rice, potatoes, lawn, corn, oilseed rape, potatoes, sugar beet, vegetables and on various other plants, for example R. solani (root and stern rot) on soybeans, R. solani (sheath blight) on rice or R. cerealis (sharp eyespot) on wheat or barley; Rhizopus stolonifer (soft rot) on strawberries, carrots, cabbage, grapevines and tomato; Rhynchosporium secalis (leaf spot) on barley, rye and triticale; Sarocladium oryzae and S. attenuatum (sheath rot) on rice; Sclerotinia spp. (stem or white rot) on vegetable and field crops, such as oilseed rape, sunflowers (e.g. Sclerotinia sclerotiorum) and soybeans (e.g. S. rolfsii),* Septoria spp. on various plants, e.g. S. glycines (leaf spot) on soybeans, S. tritici (Septoria leaf blotch) on wheat and S. (syn. Stagonospora) nodorum (leaf blotch and glume blotch) on cereals; Uncinula (syn. Erysiphe) necator (powdery mildew, anamorph: Oidium tuckeri) on grapevines; Setospaeria spp. (leaf spot) on corn (e.g. S. turcicum, syn. Helminthosporium turcicum) and lawn; Sphacelotheca spp. (head smut) on corn, (e.g. S. reiliana: kernel smut), millet and sugar cane; Sphaerotheca fuliginea (powdery mildew) on cucumber species; Spongospora subterranea (powdery scab) on potatoes and the viral diseases transmitted thereby; Stagonospora spp. on cereals, e.g. S. nodorum (leaf blotch and glume blotch, teleomorph: Leptosphaeria [syn. Phaeosphaeria] nodorum) on wheat; Synchytrium endobioticum on potatoes (potato wart disease); Taphrina spp., e.g. T. deformans (curly-leaf disease) on peach and T. pruni (plum-pocket disease) on pi urns; Thielaviopsis spp. (black root rot) on tobacco, pome fruit, vegetable crops, soybeans and cotton, e.g. T. basicola (syn. Chalara elegans); Tilletia spp. (bunt or stinking smut) on cereals, such as e.g. T. tritici (syn. T. caries, wheat bunt) and T. controversa (dwarf bunt) on wheat; Typhula incarnata (gray snow mold) on barley or wheat; Urocystis spp., e.g. U. occulta (flag smut) on rye; Uromyces spp. (rust) on vegetable plants, such as beans (e.g. U. appendiculatus, syn. U. phaseoll) and sugar beet (e.g. U. betae); Ustilago spp. (loose smut) on cereals (e.g. U. nuda and U. avaenae), corn (e.g. U. maydis: corn smut) and sugar cane; Venturia spp. (scab) on apples (e.g. V. inaequalis) and pears and Verticillium spp. (leaf and shoot wilt) on various plants, such as fruit trees and ornamental trees, grapevines, soft fruit, vegetable and field crops, such as e.g. V. dahliae on strawberries, oilseed rape, potatoes and tomatoes. The compounds according to the invention can be used for curative or protective/preventive control of harmful microorganisms. The invention therefore also relates to curative and protective methods for controlling harmful microorganisms by the use of the compounds according to the invention , which are applied to the seed, the plant or plant parts, the fruit or the soil in which the plants grow.

The fact that the compounds according to the invention are well tolerated by plants at the concentrations required for controlling harmful microorganisms allows the treatment of above-ground parts of plants, of propagation stock and seeds, and of the soil. Plant and Plant Parts

All plants and plant parts can be treated in accordance with the invention. Here, plants are to be understood to mean all plants and plant parts such as wanted and unwanted wild plants or crop plants (including naturally occurring crop plants), for example cereals (wheat, rice, triticale, barley, rye, oats), maize, soya bean, potato, sugar beet, sugar cane, tomatoes, peas and other vegetable species, cotton, tobacco, oilseed rape, and also fruit plants (with the fruits apples, pears, citrus fruits and grapevines). Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant varieties which can or cannot be protected by varietal property rights. Plant parts should be understood to mean all parts and organs of the plants above and below ground, such as shoot, leaf, flower and root, examples given being leaves, needles, stalks, stems, flowers, fruit bodies, fruits and seeds, and also tubers, roots and rhizomes. Parts of plants also include harvested plants and vegetative and generative propagation material, for example seedlings, tubers, rhizomes, cuttings and seeds.

Treatment according to the invention of the plants and plant parts with the compounds of the formula (I) is carried out directly or by allowing the compounds to act on the surroundings, environment or storage space by the customary treatment methods, for example by immersion, spraying, evaporation, fogging, scattering, painting on, injection and, in the case of propagation material, in particular in the case of seeds, also by applying one or more coats. As already mentioned above, it is possible to treat all plants and their parts according to the invention. In a preferred embodiment, wild plant species and plant cultivars, or those obtained by conventional biological breeding methods, such as crossing or protoplast fusion, and also parts thereof, are treated. In a further preferred embodiment, transgenic plants and plant cultivars obtained by genetic engineering methods, if appropriate in combination with conventional methods (genetically modified organisms), and parts thereof are treated. The term "parts" or "parts of plants" or "plant parts" has been explained above. The invention is used with particular preference to treat plants of the respective commercially customary cultivars or those that are in use. Plant cultivars are to be understood as meaning plants having new properties ("traits") and which have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. They can be cultivars, varieties, bio- or genotypes.

The compounds to be used in accordance with the invention can preferably be employed in the following plants, the enumeration which follows not being limiting.

Preferred plants are those from the group of the useful plants, ornamentals, turfs, generally used trees which are employed as ornamentals in the public and domestic sectors, and forestry trees. Forestry trees comprise trees for the production of timber, cellulose, paper and products made from parts of the trees.

The term useful plants as used in the present context refers to crop plants which are employed as plants for obtaining foodstuffs, feedstuffs, fuels or for industrial purposes.

The useful plants include, for example, the following types of plants: turf, vines, cereals, for example wheat, barley, rye, oats, triticale, rice, maize and millet/sorghum; beet, for example sugar beet and fodder beet; fruits, for example pome fruit, stone fruit and soft fruit, for example apples, pears, plums, peaches, almonds, cherries and berries, for example strawberries, raspberries, blackberries; legumes, for example beans, lentils, peas and soya beans; oil crops, for example oilseed rape, mustard, poppies, olives, sunflowers, coconuts, castor oil plants, cacao beans and peanuts; cucurbits, for example pumpkin/squash, cucumbers and melons; fibre plants, for example cotton, flax, hemp and jute; citrus fruit, for example oranges, lemons, grapefruit and tangerines; vegetables, for example spinach, lettuce, asparagus, cabbage species, carrots, onions, tomatoes, potatoes and bell peppers; Lauraceae, for example avocado, Cinnamomum, camphor, or also plants such as tobacco, nuts, coffee, aubergine, sugar cane, tea, pepper, grapevines, hops, bananas, latex plants and ornamentals, for example flowers, shrubs, deciduous trees and coniferous trees such as conifers. This enumeration does not constitute a limitation. Particularly suitable target crops are the plants below: cotton, aubergine, turf, pome fruit, stone fruit, soft fruit, maize, wheat, barley, cucumber, tobacco, vines, rice, cereals, pear, beans, soya beans, oilseed rape, tomato, bell pepper, melons, cabbage, potatoes and apples. Examples of trees include: Abies sp., Eucalyptus sp., Picea sp., Pinus sp., Aesculus sp., Platanus sp., Tilia sp., Acer sp., Tsuga sp., Fraxinus sp., Sorbus sp., Betula sp., Crataegus sp., Ulmus sp., Quercus sp., Fagus sp., Salix sp., Populus sp.

Preferred trees which may be mentioned are: from the tree species Aesculus: A. hippocastanum, A. pariflora, A. carnea; from the tree species Platanus: P. aceriflora, P. occidentalis, P. racemosa; from the tree species Picea: P. abies; from the tree species Pinus: P. radiate, P. ponderosa, P. contorta, P. sylvestre, P. elliottii, P. montecola, P. albicaulis, P. resinosa, P. palustris, P. taeda, P. flexilis, P. jeffregi, P. baksiana, P. strobes; from the tree species Eucalyptus: E. grandis, E. globulus, E. camadentis, E. nitens, E. obliqua, E. regnans, E. pilularus. Particularly preferred trees which may be mentioned are: from the tree species Pinus: P. radiate, P. ponderosa, P. contorta, P. sylvestre, P. strobes; from the tree species Eucalyptus: E. grandis, E. globulus, E. camadentis.

Very particularly preferred trees which may be mentioned are: horse chestnut, Platanaceae, linden tree, maple tree. The present invention can also be applied to any turfgrasses, including cool-season turfgrasses and warm-season turfgrasses. Examples of cool-season turfgrasses are bluegrasses {Poa spp.), such as Kentucky bluegrass {Poa pratensis L.), rough bluegrass {Poa trivialis L.), Canada bluegrass {Poa compressa L.), annual bluegrass {Poa annua L.), upland bluegrass {Poa glaucantha Gaudin), wood bluegrass {Poa nemoralis L.) and bulbous bluegrass {Poa bulbosa L.); bentgrasses {Agrostis spp.) such as creeping bentgrass {Agrostis palustris Huds.), colonial bentgrass {Agrostis tenuis Sibth.), velvet bentgrass {Agrostis canina L.), South German Mixed Bentgrass {Agrostis spp. including Agrostis tenius Sibth., Agrostis canina L., and Agrostis palustris Huds.), and redtop {Agrostis alba L.); fescues {Festuca spp.), such as red fescue {Festuca rubra L. spp. rubra), creeping fescue {Festuca rubra L.), chewings fescue {Festuca rubra commutata Gaud.), sheep fescue {Festuca ovina L.), hard fescue {Festuca longifolia Thuill.), hair fescue {Festucu capillata Lam.), tall fescue {Festuca arundinacea Schreb.) and meadow fescue {Festuca elanor L.); ryegrasses {Lolium spp.), such as annual ryegrass {Lolium multiflorum Lam.), perennial ryegrass {Lolium perenne L.) and Italian ryegrass {Lolium multiflorum Lam.); and wheatgrasses {Agropyron spp.), such as fairway wheatgrass {Agropyron cristatum (L.) Gaertn.), crested wheatgrass {Agropyron desertorum (Fisch.) Schult.) and western wheatgrass {Agropyron smithii Rydb.).

Examples of further cool-season turfgrasses are beachgrass {Ammophila breviligulata Fern.), smooth bromegrass {Bromus inermis Leyss.), cattails such as Timothy {Phleum pratense L.), sand cattail (Phleum subulatum L.), orchard grass (Dactylis glomerata L.), weeping alkaligrass (PuccinelUa distans (L.) Pari.) and crested dog's-tail (Cynosurus cristatus L.).

Examples of warm-season turfgrasses are Bermuda grass (Cynodon spp. L. C. Rich), zoysia grass {Zoysia spp. Willd.), St. Augustine grass (Stenotaphrum secundatum Walt Kuntze), centipede grass (Eremochloa ophiuroides Munro Hack.), carpet grass (Axonopus affinis Chase), Bahia grass {Paspalum notatum Flugge), Kikuyu grass (Pennisetum clandestinum Hochst. ex Chiov.), buffalo grass (Buchloe dactyloids (Nutt.) Engelm.), Blue gramma {Bouteloua gracilis (H.B.K.) Lag. ex Griffiths), seashore paspalum (Paspalum vaginatum Swartz) and sideoats grama {Bouteloua curtipendula (Michx. Torr.). Cool-season turfgrasses are generally preferred for the use in accordance with the invention. Particular preference is given to bluegrass, bentgrass and redtop, fescues and ryegrasses. Bentgrass is especially preferred.

Particularly useful transgenic plants which may be treated according to the invention are plants containing transformation events, or a combination of transformation events, and that are listed for example in the databases for various national or regional regulatory agencies including Event 531/ PV- GHBK04 (cotton, insect control, described in WO 2002/040677), Event 1143-14A (cotton, insect control, not deposited, described in WO 06/128569); Event 1143-51B (cotton, insect control, not deposited, described in WO 06/128570); Event 1445 (cotton, herbicide tolerance, not deposited, described in US-A 2002-120964 or WO 02/034946Event 17053 (rice, herbicide tolerance, deposited as PTA-9843, described in WO 10/117737); Event 17314 (rice, herbicide tolerance, deposited as PTA- 9844, described in WO 10/117735); Event 281-24-236 (cotton, insect control - herbicide tolerance, deposited as PTA-6233, described in WO 05/103266 or US-A 2005-216969); Event 3006-210-23 (cotton, insect control - herbicide tolerance, deposited as PTA-6233, described in US-A 2007-143876 or WO 05/103266); Event 3272 (corn, quality trait, deposited as PTA-9972, described in WO 06/098952 or US-A 2006-230473); Event 33391 (wheat, herbicide tolerance, deposited as PTA-2347, described in WO 2002/027004), Event 40416 (corn, insect control - herbicide tolerance, deposited as ATCC PTA- 11508, described in WO 1 1/075593); Event 43A47 (corn, insect control - herbicide tolerance, deposited as ATCC PTA-11509, described in WO 11/075595); Event 5307 (corn, insect control, deposited as ATCC PTA-9561, described in WO 10/077816); Event ASR-368 (bent grass, herbicide tolerance, deposited as ATCC PTA-4816, described in US-A 2006-162007 or WO 04/053062); Event B16 (corn, herbicide tolerance, not deposited, described in US-A 2003-126634); Event BPS-CV127-9 (soybean, herbicide tolerance, deposited as NCIMB No. 41603, described in WO 10/080829); Event BLR1 (oilseed rape, restoration of male sterility, deposited as NCIMB 41193, described in WO 2005/074671), Event CE43-67B (cotton, insect control, deposited as DSM ACC 2 724, described in US-A 2009-217423 or WO 06/128573); Event CE44-69D (cotton, insect control, not deposited, described in US-A 2010- 0024077); Event CE44-69D (cotton, insect control, not deposited, described in WO 06/128571); Event CE46-02A (cotton, insect control, not deposited, described in WO 06/128572); Event COT102 (cotton, insect control, not deposited, described in US-A 2006-130175 or WO 04/039986); Event COT202 (cotton, insect control, not deposited, described in US-A 2007-067868 or WO 05/054479); Event COT203 (cotton, insect control, not deposited, described in WO 05/054480); ); Event DAS21606-3 / 1606 (soybean, herbicide tolerance, deposited as PTA-11028, described in WO 012/033794), Event DAS40278 (corn, herbicide tolerance, deposited as ATCC PTA-10244, described in WO 11/022469); Event DAS-44406-6 / pDAB8264.44.06.1 (soybean, herbicide tolerance, deposited as PTA-11336, described in WO 2012/075426), Event DAS-14536-7 /pDAB8291.45.36.2 (soybean, herbicide tolerance, deposited as PTA-11335, described in WO 2012/075429), Event DAS-59122-7 (corn, insect control - herbicide tolerance, deposited as ATCC PTA 11384 , described in US-A 2006-070139); Event DAS-59132 (corn, insect control - herbicide tolerance, not deposited, described in WO 09/100188); Event DAS68416 (soybean, herbicide tolerance, deposited as ATCC PTA- 10442, described in WO 11/066384 or WO 11/066360); Event DP-098140-6 (corn, herbicide tolerance, deposited as ATCC PTA- 8296, described in US-A 2009-137395 or WO 08/112019); Event DP-305423-1 (soybean, quality trait, not deposited, described in US-A 2008-312082 or WO 08/054747); Event DP-32138-1 (corn, hybridization system, deposited as ATCC PTA-9158, described in US-A 2009-0210970 or WO 09/103049); Event DP-356043-5 (soybean, herbicide tolerance, deposited as ATCC PTA-8287, described in US-A 2010-0184079 or WO 08/002872); Event EE-1 (brinjal, insect control, not deposited, described in WO 07/091277); Event FI117 (corn, herbicide tolerance, deposited as ATCC 209031, described in US-A 2006-059581 or WO 98/044140); Event FG72 (soybean, herbicide tolerance, deposited as PTA-11041, described in WO 2011/063413), Event GA21 (corn, herbicide tolerance, deposited as ATCC 209033, described in US-A 2005-086719 or WO 98/044140); Event GG25 (corn, herbicide tolerance, deposited as ATCC 209032, described in US-A 2005-188434 or WO 98/044140); Event GHBl 19 (cotton, insect control - herbicide tolerance, deposited as ATCC PTA-8398, described in WO 08/151780); Event GHB614 (cotton, herbicide tolerance, deposited as ATCC PTA-6878, described in US-A 2010-050282 or WO 07/017186); Event GJ11 (corn, herbicide tolerance, deposited as ATCC 209030, described in US-A 2005-188434 or WO 98/044140); Event GM RZ13 (sugar beet, virus resistance , deposited as NCIMB-41601, described in WO 10/076212); Event H7-1 (sugar beet, herbicide tolerance, deposited as NCIMB 41158 or NCIMB 41159, described in US-A 2004-172669 or WO 04/074492); Event JOPLINl (wheat, disease tolerance, not deposited, described in US-A 2008- 064032); Event LL27 (soybean, herbicide tolerance, deposited as NCIMB41658, described in WO 06/108674 or US-A 2008-320616); Event LL55 (soybean, herbicide tolerance, deposited as NCIMB 41660, described in WO 06/108675 or US-A 2008-196127); Event LLcotton25 (cotton, herbicide tolerance, deposited as ATCC PTA-3343, described in WO 03/013224 or US-A 2003-097687); Event LLRICE06 (rice, herbicide tolerance, deposited as ATCC 203353, described in US 6,468,747 or WO 00/026345); Event LLRice62 ( rice, herbicide tolerance, deposited as ATCC 203352, described in WO 2000/026345), Event LLRICE601 (rice, herbicide tolerance, deposited as ATCC PTA-2600, described in US-A 2008-2289060 or WO 00/026356); Event LY038 (corn, quality trait, deposited as ATCC PTA- 5623, described in US-A 2007-028322 or WO 05/061720); Event MIR162 (corn, insect control, deposited as PTA-8166, described in US-A 2009-300784 or WO 07/142840); Event MIR604 (corn, insect control, not deposited, described in US-A 2008-167456 or WO 05/103301); Event MON15985 (cotton, insect control, deposited as ATCC PTA-2516, described in US-A 2004-250317 or WO 02/100163); Event MON810 (corn, insect control, not deposited, described in US-A 2002-102582); Event MON863 (corn, insect control, deposited as ATCC PTA-2605, described in WO 04/011601 or US-A 2006-095986); Event MON87427 (corn, pollination control, deposited as ATCC PTA-7899, described in WO 11/062904); Event MON87460 (corn, stress tolerance, deposited as ATCC PTA-8910, described in WO 09/111263 or US-A 2011-0138504); Event MON87701 (soybean, insect control, deposited as ATCC PTA-8194, described in US-A 2009-130071 or WO 09/064652); Event MON87705 (soybean, quality trait - herbicide tolerance, deposited as ATCC PTA-9241, described in US-A 2010- 0080887 or WO 10/037016); Event MON87708 (soybean, herbicide tolerance, deposited as ATCC PTA-9670, described in WO 11/034704); Event MON87712 (soybean, yield, deposited as PTA-10296, described in WO 2012/051199), Event MON87754 (soybean, quality trait, deposited as ATCC PTA- 9385, described in WO 10/024976); Event MON87769 (soybean, quality trait, deposited as ATCC PTA- 8911, described in US-A 2011-0067141 or WO 09/102873); Event MON88017 (corn, insect control - herbicide tolerance, deposited as ATCC PTA-5582, described in US-A 2008-028482 or WO 05/059103); Event MON88913 (cotton, herbicide tolerance, deposited as ATCC PTA-4854, described in WO 04/072235 or US-A 2006-059590); Event MON88302 (oilseed rape, herbicide tolerance, deposited as PTA-10955, described in WO 2011/153186), Event MON88701 (cotton, herbicide tolerance, deposited as PTA-11754, described in WO 2012/134808), Event MON89034 (corn, insect control, deposited as ATCC PTA-7455, described in WO 07/140256 or US-A 2008-260932); Event MON89788 (soybean, herbicide tolerance, deposited as ATCC PTA-6708, described in US-A 2006-282915 or WO 06/130436); Event MS 11 (oilseed rape, pollination control - herbicide tolerance, deposited as ATCC PTA-850 or PTA-2485, described in WO 01/031042); Event MS8 (oilseed rape, pollination control - herbicide tolerance, deposited as ATCC PTA-730, described in WO 01/041558 or US-A 2003-188347); Event NK603 (corn, herbicide tolerance, deposited as ATCC PTA-2478, described in US-A 2007- 292854); Event PE-7 (rice, insect control, not deposited, described in WO 08/114282); Event RF3 (oilseed rape, pollination control - herbicide tolerance, deposited as ATCC PTA-730, described in WO 01/041558 or US-A 2003-188347); Event RT73 (oilseed rape, herbicide tolerance, not deposited, described in WO 02/036831 or US-A 2008-070260); Event SYHT0H2 / SYN-000H2-5 (soybean, herbicide tolerance, deposited as PTA-11226, described in WO 2012/082548), Event T227-1 (sugar beet, herbicide tolerance, not deposited, described in WO 02/44407 or US-A 2009-265817); Event T25 (corn, herbicide tolerance, not deposited, described in US-A 2001-029014 or WO 01/051654); Event T304-40 (cotton, insect control - herbicide tolerance, deposited as ATCC PTA-8171, described in US-A 2010-077501 or WO 08/122406); Event T342-142 (cotton, insect control, not deposited, described in WO 06/128568); Event TC1507 (corn, insect control - herbicide tolerance, not deposited, described in US-A 2005-039226 or WO 04/099447); Event VIP1034 (corn, insect control - herbicide tolerance, deposited as ATCC PTA-3925., described in WO 03/052073), Event 32316 (corn, insect control- herbicide tolerance, deposited as PTA-11507, described in WO 11/084632), Event 4114 (corn, insect control-herbicide tolerance, deposited as PTA-11506, described in WO 11/084621), event EE-GM3 / FG72 (soybean, herbicide tolerance, ATCC Accession N° PTA-11041, WO 2011/063413A2), event DAS-68416-4 (soybean, herbicide tolerance, ATCC Accession N° PTA-10442, W02 011/066360A1), event DAS-68416-4 (soybean, herbicide tolerance, ATCC Accession N° PTA-10442, WO 2011/066384A1), event DP-040416-8 (corn, insect control, ATCC Accession N° PTA-11508, WO 2011/075593A1), event DP-043A47-3 (corn, insect control, ATCC Accession N° PTA-11509, WO 2011/075595A1), event DP-004114-3 (corn, insect control, ATCC Accession N° PTA-11506, WO 2011/084621A1), event DP-032316-8 (corn, insect control, ATCC Accession N° PTA-11507, WO 2011/084632A1), event MON-88302-9 (oilseed rape, herbicide tolerance, ATCC Accession N° PTA- 10955, WO 2011/153186A1), event DAS-21606-3 (soybean, herbicide tolerance, ATCC Accession No. PTA-11028, WO 2012/033794A2), event MON-87712-4 (soybean, quality trait, ATCC Accession N°. PTA-10296, WO 2012/051199A2), event DAS-44406-6 (soybean, stacked herbicide tolerance, ATCC Accession N°. PTA-11336, WO 2012/075426A1), event DAS-14536-7 (soybean, stacked herbicide tolerance, ATCC Accession N°. PTA-11335, WO 2012/075429A1), event SYN-000H2-5 (soybean, herbicide tolerance, ATCC Accession N°. PTA-11226, WO 2012/082548A2), event DP-061061-7 (oilseed rape, herbicide tolerance, no deposit N° available, WO 2012071039A1), event DP-073496-4 (oilseed rape, herbicide tolerance, no deposit N° available, US2012131692), event 8264.44.06.1 (soybean, stacked herbicide tolerance, Accession N° PTA-11336, WO 2012075426A2), event 8291.45.36.2 (soybean, stacked herbicide tolerance, Accession N°. PTA-11335, WO 2012075429A2), event SYHT0H2 (soybean, ATCC Accession N°. PTA-11226, WO 2012/082548A2), event MON88701 (cotton, ATCC Accession N° PTA-11754, WO 2012/134808A1), event KK179-2 (alfalfa, ATCC Accession N° PTA-11833, WO2013003558A1), event pDAB8264.42.32.1 (soybean, stacked herbicide tolerance, ATCC Accession N° PTA-11993, WO 2013010094A1), event MZDT09Y (corn, ATCC Accession N° PTA-13025, WO 2013012775A1), event KK179-2 (alfalfa, ATCC Accession N° PTA- 11833, WO2013003558A1), event pDAB8264.42.32.1 (soybean, stacked herbicide tolerance, ATCC Accession N° PTA-1 1993, WO2013010094A1), event MZDT09Y (corn, ATCC Accession N° PTA- 13025, WO2013012775A1), event VCO-01981-5 (corn, herbicide tolerance, NCIMB Accession N° 41842, WO2013014241A1), event DAS-81419-2 X DAS-68416-4 (soybean stacked insect resistance and herbicide tolerance, ATCC Accession N° PTA- 10442, WO2013016516A1), event DAS-81419-2 (soybean stacked insect resistance and herbicide tolerance, ATCC Accession N° PTA- 12006, WO2013016527A1), event HCEM485 (corn, herbicide tolerance, ATCC Accession N° PTA-12014, WO2013025400A1), event pDAB4468.18.07.1 (cotton, herbicide tolerance, ATCC Accession N° PTA- 12456, WO2013112525 A2), event pDAB4468.19.10.3 (cotton, herbicide tolerance, ATCC Accession N° PTA-12457, WO2013112527A1). Crop protection - types of treatment

The treatment of the plants and plant parts with the compounds of the formula (I) is carried out directly or by action on their surroundings, habitat or storage space using customary treatment methods, for example by dipping, spraying, atomizing, irrigating, evaporating, dusting, fogging, broadcasting, foaming, painting, spreading-on, injecting, watering (drenching), drip irrigating and, in the case of propagation material, in particular in the case of seed, furthermore as a powder for dry seed treatment, a solution for liquid seed treatment, a water-soluble powder for slurry treatment, by incrusting, by coating with one or more coats, etc. It is furthermore possible to apply the compounds of the formula (I) by the ultra- low volume method or to inject the application form or the compound of the formula (I) itself into the soil.

A preferred direct treatment of the plants is foliar application, i.e. the compounds of the formula (I) are applied to the foliage, where treatment frequency and the application rate should be adjusted according to the level of infestation with the harmful microorganism in question.

In the case of systemically active compounds, the compounds of the formula (I) also access the plants via the root system. The plants are then treated by the action of the compounds of the formula (I) on the habitat of the plant. This may be done, for example, by drenching, or by mixing into the soil or the nutrient solution, i.e. the locus of the plant (e.g. soil or hydroponic systems) is impregnated with a liquid form of the compounds of the formula (I), or by soil application, i.e. the compounds of the formula (I) according to the invention are introduced in solid form (e.g. in the form of granules) into the locus of the plants. In the case of paddy rice crops, this can also be done by metering the compound of the formula (I) in a solid application form (for example as granules) into a flooded paddy field.

Application Rates and Timing

When using the compounds according to the invention as fungicides, the application rates can be varied within a relatively wide range, depending on the kind of application. The application rate of the compounds according to the invention is

• in the case of treatment of plant parts, for example leaves: from 0.1 to 10 000 g/ha, preferably from 10 to 1000 g/ha, more preferably from 10 to 800 g/ha, even more preferably from 50 to 300 g/ha (in the case of application by watering or dripping, it is even possible to reduce the application rate, especially when inert substrates such as rockwool or perlite are used); · in the case of seed treatment: from 2 to 200 g per 100 kg of seed, preferably from 3 to 150 g per 100 kg of seed, more preferably from 2.5 to 25 g per 100 kg of seed, even more preferably from 2.5 to 12.5 g per 100 kg of seed; in the case of soil treatment: from 0.1 to 10 000 g/ha, preferably from 1 to 5000 g/ha. These application rates are merely by way of example and are not limiting for the purposes of the invention.

The compounds according to the invention can thus be used to protect plants from attack by the pathogens mentioned for a certain period of time after treatment. The period for which protection is provided extends generally for 1 to 28 days, preferably for 1 to 14 days, more preferably for 1 to 10 days, most preferably for 1 to 7 days, after the treatment of the plants with the active ingredients, or for up to 200 days after a seed treatment.

Mycotoxins

In addition, the inventive treatment can reduce the mycotoxin content in the harvested material and the foods and feeds prepared therefrom. Mycotoxins include particularly, but not exclusively, the following: deoxynivalenol (DON), nivalenol, 15-Ac-DON, 3-Ac-DON, T2- and HT2 -toxin, fumonisins, zearalenon, moniliformin, fusarin, diaceotoxyscirpenol (DAS), beauvericin, enniatin, fusaroproliferin, fusarenol, ochratoxins, patulin, ergot alkaloids and aflatoxins which can be produced, for example, by the following fungi: Fusarium spec, such as F. acuminatum, F. asiaticum, F. avenaceum, F. crookwellense, F. culmorum, F. graminearum (Gibberella zeae), F. equiseti, F. fujikoroi, F. musarum, F. oxysporum, F. proliferatum, F. poae, F. pseudograminearum, F. sam-'bucinum, F. scirpi, F. semitectum, F. solani, F. sporotrichoides, F. langsethiae, F. subglutinans, F. tricinctum, F. verticillioides etc., and also by Aspergillus spec, such as A. flavus, A. parasiticus, A. nomius, A. ochraceus, A. clavatus, A. terreus, A. versicolor, Penicillium spec, such as P. verrucosum, P. viridicatum, P. citrinum, P. expansum, P. claviforme, P. roqueforti, Claviceps spec, such as C. purpurea, C. fusiformis, C. paspali, C. africana, Stachybotrys spec, and others.

Material Protection

The compounds according to the invention can also be used in the protection of materials, for protection of industrial materials against attack and destruction by unwanted microorganisms, for example fungi, and insects.

In addition, the inventive compoundscan be used as antifouling compositions, alone or in combinations with other active ingredients.

Industrial materials in the present context are understood to mean inanimate materials which have been prepared for use in industry. For example, industrial materials which are to be protected by compoundsaccording to the invention from microbial alteration or destruction may be adhesives, glues, paper, wallpaper and board/cardboard, textiles, carpets, leather, wood, fibers and tissues, paints and plastic articles, cooling lubricants and other materials which can be infected with or destroyed by microorganisms. Parts of production plants and buildings, for example cooling-water circuits, cooling and heating systems and ventilation and air-conditioning units, which may be impaired by the proliferation of microorganisms may also be mentioned within the scope of the materials to be protected. Industrial materials within the scope of the present invention preferably include adhesives, sizes, paper and card, leather, wood, paints, cooling lubricants and heat transfer fluids, more preferably wood. The compoundsaccording to the invention may prevent adverse effects, such as rotting, decay, discoloration, decoloration or formation of mould.

In the case of treatment of wood the compounds/compositions according to the invention may also be used against fungal diseases liable to grow on or inside timber. The term "timber" means all types of species of wood, and all types of working of this wood intended for construction, for example solid wood, high density wood, laminated wood, and plywood. The method for treating timber according to the invention mainly consists in contacting one or more compounds according to the invention or a compoundsaccording to the invention; this includes for example direct application, spraying, dipping, injection or any other suitable means.

In addition, the inventive compounds can be used to protect objects which come into contact with saltwater or brackish water, especially hulls, screens, nets, buildings, moorings and signalling systems, from fouling.

The inventive method for controlling unwanted microorganisms can also be employed for protecting storage goods. Storage goods are understood to mean natural substances of vegetable or animal origin or processed products thereof which are of natural origin, and for which long-term protection is desired. Storage goods of vegetable origin, for example plants or plant parts, such as stems, leaves, tubers, seeds, fruits, grains, can be protected freshly harvested or after processing by (pre)drying, moistening, comminuting, grinding, pressing or roasting. Storage goods also include timber, both unprocessed, such as construction timber, electricity poles and barriers, or in the form of finished products, such as furniture. Storage goods of animal origin are, for example, hides, leather, furs and hairs. The compositions according to the invention may prevent adverse effects, such as rotting, decay, discoloration, decoloration or formation of mould.

Microorganisms capable of degrading or altering the industrial materials include, for example, bacteria, fungi, yeasts, algae and slime organisms. The compoundsaccording to the invention preferably act against fungi, especially moulds, wood-discoloring and wood-destroying fungi (Ascomycetes, Basidiomycetes, Deuteromycetes and Zygomycetes), and against slime organisms and algae. Examples include microorganisms of the following genera: Alternaria, 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 glaucum; Polyporus, such as Polyporus versicolor; Aureobasidium, such as Aureobasidium pullulans; Sclerophoma, such as Sclerophoma pityophila; Trichoderma, such as Trichoderma viride; Ophiostoma spp., Ceratocystis spp., Humicola spp., Petriella spp., Trichurus spp., Coriolus spp., Gloeophyllum spp., Pleurotus spp., Poria spp., Serpula spp. and Tyromyces spp., Cladosporium spp., Paecilomyces spp. Mucor spp., Escherichia, such as Escherichia coli; Pseudomonas, such as Pseudomonas aeruginosa; Staphylococcus, such as Staphylococcus aureus, Candida spp. and Saccharomyces spp., such as Saccharomyces cerevisae.

The Preparation and Use Examples which follow illustrate the invention without limiting it.

Synthesis Example 1

N-[l-(2,6-Difluorophenyl)-lH-pyrazol-3-yl]-3-(trifluorome thyl)pyridine-2-carboxamide

(Compound 1-1-91 in Table 1) Step 1 : N-[l-(2,6-Difluorophenyl)-4,5-dihydro-lH-pyrazol-3-yl]acetam ide

With ice cooling, l-(2,6-difluorophenyl)-4,5-dihydro-lH-pyrazole-3-amine (1.40 g as a crude mixture from Synthesis Example 6, Step 1) was dissolved in acetic anhydride (6 ml) and stirred at room temperature overnight. The mixture was then diluted with ethyl acetate, washed with water, dried over sodium sulphate and concentrated to dryness under reduced pressure. The residue was purified by column chromatography on silica gel using the mobile phase cyclohexane/ethyl acetate (gradient = 2 h from 100% cyclohexane to 100% ethyl acetate). This gave 537 mg of the title compound. HPLC-MS: logP = 1.46; mass (m/z): 240.0 (M+H) + ; 'H-NMR (DMSO-D 6 ) 1.99 (s, 3H), 3.26 (t, 2H), 3.65 (t, 2H), 7.04 - 7.10 (m, 2H), 7.11 - 7.18 (m, 1H), 10.59 (br. s, 1H). Step 2: N-[l-(2,6-Difluorophenyl)-lH-pyrazol-3-yl]acetamide

N-[l-(2,6-Difluorophenyl)-4,5-dihydro-lH-pyrazol-3-yl]ace tamide (200 mg) was initially charged in 1,4-dioxane (1 ml), 2,3-dichloro-5,6-dicyano-l,4-benzoquinone (209 mg) was added and the mixture was stirred at room temperature for 30 min. The reaction mixture was filtered and the filtrate was concentrated to dryness under reduced pressure. The residue was purified by column chromatography on silica gel using the mobile phase cyclohexane/ethyl acetate (gradient = 2 h from 100%) cyclohexane to 100% ethyl acetate). This gave 140 mg of the title compound. HPLC-MS: logP = 1.33; mass (m/z): 238.0 (M+H) + ; 'H-NMR (CD 3 CN) 2.07 (s, 3H), 6.84 (d, 1H), 7.14 - 7.20 (m, 2H), 7.47 - 7.53 (m, 7.65 - 7.66 (m, 1H), 8.76 (br. s, 1H).

Step 3: l-(2, 6-Difluorophenyl)-lH-pyrazole-3-amine (via route D-l)

N-[l-(2,6-Difluorophenyl)-lH-pyrazol-3-yl]acetamide (50 mg) was initially charged in water (1 ml), concentrated hydrochloric acid (0.07 ml) was added and the mixture was heated under reflux for 8 h. The reaction mixture was then made alkaline with concentrated aqueous sodium hydroxide solution and extracted with dichloromethane. The organic phase was concentrated to dryness under reduced pressure. This gave 25 mg of the title compound. HPLC-MS: logP = 1.13; mass (m/z): 196.1 (M+H) + ; 'H-NMR (CD 3 CN) 4.12 (br. s, 2H), 5.83 (d, 1H), 7.09 - 7.16 (m, 2H), 7.37 - 7.44 (m, 1H), 7.46 - 7.47 (m, 1H).

Step 4: N-f l-(2, 6-Difluorophenyl)-lH^yrazol-3-yl]-3-(trifluoromethyl)pyridin e-2-carboxamide

3-(Trifluoromethyl)pyridine-2-carboxylic acid (76 mg) was initially charged in dichloromethane (2 ml), l-ethyl-3-(3-dimethylaminopropyl)carbodiimide (95 mg) and 1 -hydroxy- lH-benzotriazole (67 mg) were added at 0°C and the mixture was stirred for 1 h. A solution of l-(2,6-difluorophenyl)-lH-pyrazole-3- amine (66 mg) in dichloromethane (1 ml) was then added, and the mixture was stirred at room temperature overnight. The reaction mixture was then diluted with dichloromethane, washed with water, dried over sodium sulphate and concentrated to dryness under reduced pressure. The residue was initially purified by column chromatography on silica gel using the mobile phase cyclohexane/ethyl acetate (gradient = 2 h from 100% cyclohexane to 100% ethyl acetate) and then chromatographed by preparative HPLC using the mobile phase water/acetonitrile (gradient = 40 min from 10%> acetonitrile in water to 100%) acetonitrile). This gave 55 mg of the title compound. HPLC-MS: logP = 2.22; mass (m/z): 369.0 (M+H) + ; 'H-NMR (CD 3 CN) 6.98 - 6.99 (m, 1H), 7.17 - 7.21 (m, 2H), 7.48 - 7.55 (m, 1H), 7.66 - 7.73 (m, 1H), 7.76 - 7.77 (m, 1H), 8.08 - 8.10 (m, 1H), 8.80 - 8.82 (m, 1H), 9.30 (br. s, 1H). Synthesis Example 2

N-[l-(2,6-Dichlorophenyl)-lH-pyrazol-3-yl]-2-iodobenzamid e (Compound 1-1-123 in Table 1)

Step 1 : l-(2, 6-Dichlorophenyl)-lH-pyrazole-3-amine (via route

2,6-Dichlorophenylhydrazine (10.0 g) was initially charged in ethanol (65 ml), sodium methoxide solution (3.04 g in 35 ml of ethanol) and 3-ethoxyacrylonitrile (6.82 g) were added, and the mixture was stirred at 80°C for 12 h and at room temperature for 2 d. The reaction mixture was then concentrated under reduced pressure, taken up in ethyl acetate, washed with water, dried over sodium sulphate and concentrated to dryness under reduced pressure. The residue was purified by column chromatography on silica gel using the mobile phase cyclohexane/ethyl acetate (gradient = 2 h from 100% cyclohexane to 100% ethyl acetate). This gave 832 mg of the title compound. HPLC-MS: logP = 1.47; mass (m/z): 228.1 (M+H) + ; 'H-NMR (CD 3 CN) 4.09 (br. s, 2H), 5.81 (d, 1H), 7.35 - 7.43 (m, 2H), 7.51 - 7.53 (m, 2H).

Step 2: N-f l-(2, 6-Dichlorophenyl)-l H-pyrazol-3-yl] -2-iodobenzamide

l-(2,6-Dichlorophenyl)-lH-pyrazole-3 -amine (150 mg) was initially charged in dichloromethane (2 ml), triethylamine (0.28 ml) and a solution of 2-iodobenzoyl chloride (175 mg) in dichloromethane (1 ml) were added at 0°C and the mixture was stirred at room temperature overnight. The reaction mixture was then diluted with dichloromethane, washed with water, dried over sodium sulphate and concentrated to dryness under reduced pressure. The residue was purified by column chromatography on silica gel using the mobile phase cyclohexane/ethyl acetate (gradient = 2 h from 100%) cyclohexane to 100%) ethyl acetate). This gave 150 mg of the title compound. HPLC-MS: logP = 3.04; mass (m/z): 457.9 (M+H) + ; 'H-NMR (CD 3 CN) 6.99 - 7.00 (m, 1H), 7.18 - 7.23 (m, 1H), 7.46 - 7.52 (m, 3H), 7.56 - 7.58 (m, 2H), 7.66 - 7.67 (m, 1H), 7.94 - 7.96 (m, 1H), 9.16 (br. s, 1H). Synthesis Example 3

2-Bromo-N-[l-(3,5,6-trifluoropyridin-2-yl)-lH-pyrazol-3-y l]benzamide (Compound 1-1-164 in Table 1)

Step 1 : l-(3,5, 6-Trifluoropyridin-2-yl)-lH-pyrazole-3-amine (via route A-l)

lH-Pyrazole-3 -amine (2.00 g) was initially charged in acetonitrile (75 ml), 2,3,5, 6-tetrafluoropyridine (3.64 g) and potassium carbonate (6.65 g) were added and the mixture was heated under reflux overnight. The reaction mixture was subsequently triturated with tert-butyl methyl ether and filtered. The filtrate was concentrated to dryness under reduced pressure. What remained were 2.51 g of the title compound. HPLC-MS: logP = 1.15; mass (m/z): 215.1 (M+H) + ; 'H-NMR (DMSO-D 6 ) 5.35 (br. s, 2H), 5.86 (d, 1H), 8.00 (d, 1H), 8.40 - 8.45 (m, 1H).

Step 2: 2-Bromo-N-f l-(3, 5, 6-trifluoropyridin-2-yl)-lH-pyrazol-3-yl]benzamide

Analogously to Synthesis Example 9 Step 2, l-(3,5,6-trifluoropyridin-2-yl)-lH-pyrazole-3-amine (150 mg) was reacted with 2-bromobenzoyl chloride (169 mg) and triethylamine (0.29 ml) in dichloromethane. Purification by column chromatography gave 145 mg of the title compound. HPLC- MS: logP = 2.68; mass (m/z): 396.9 (M+H) + ; 1H-NMR [DMSO-D 6 ] 7.02 (d, 1H), 7.38 - 7.43 (m, 1H), 7.45 - 7.49 (m, 1H), 7.53 - 7.55 (m, 1H), 7.68 - 7.70 (m, 1H), 8.32 (d, 1H), 8.55 - 8.61 (m, 1H), 11.41 (s, 1H). Synthesis Example 5

N-[2-(2, 6-Difluorophenyl)-2H-l,2,3-triazol-4-yl]-2-(trifluoromethyl) benzamide ( Compound 1-2-35 in Table 5)

Synthesis scheme for the intermediate 2-(2, 6-difluorophenyl)-2H-l,2,3-triazole-4-amine (IX) (via A-3)

Step 1 : 2-[2-(2, 6-Difluorophenyl)hydrazinylidene]propanal oxime (Ex. 21-11)

0.1 mol of 2,6-difluorophenylhydrazine (Ex. 21-1) and 0.12 mol of isonitrosoacetone were heated under reflux in ethanol for 3 h. After cooling to room temperature, the precipitated solid was filtered off, washed with ethanol and dried. This gave 75% of theory of the hydrazone oxime (Ex. 21-11). Step 2: 2-(2, 6-Difluorophenyl)-4-methyl-2H-l,2,3-triazole (Ex. 21 -III)

A solution of 0.1 mol of the hydrazone oxime (Ex. 21-11) in acetic anhydride was heated slowly to 120°C and stirred at this temperature for 2 h. Excess acetic anhydride was removed on a rotary evaporator. The methyltriazole formed (Ex. 21 -III) (65% of theory) was processed further without further work-up. Step 3: 2-(2, 6-Difluorophenyl)-2H-l,2,3-triazole-4-carboxylic acid (Ex. 21 -IV)

A little at a time, 0.2 mol of sodium dichromate was added to a well-stirred solution of 0.1 mol of methyltriazole (Ex. 21 -III) in 66%> strength sulphuric acid. Each individual portion of dichromate was added only after the yellow-orange colour of the Cr 6+ in the flask had disappeared. Moreover, the portions were added such that the temperature in the flask remained at about 80-90°C. The mixture was then heated on a steam bath for 1 h. After cooling, the mixture was poured into about the same amount of ice and allowed to stand overnight. The precipitated acid (Ex. 21 -IV) was filtered off, washed with water and dried. This gave 50%> of theory of the acid (Ex. 21 -IV).

Step 4: Methyl 2-(2,6-difluorophenyl)-2H-l ,2, 3-triazole-4-carboxylate (Ex. 21-V)

Hydrogen chloride was bubbled for 2 h through a boiling solution of the acid (Ex. 21 -IV) in methanol. After cooling, white crystals of the ester (Ex. 21-V) were filtered off (85%> of theory).

Step 5: 2-(2,6-Difluorophenyl)-2H-l,2,3-triazole-4-carbohydrazide (Ex. 21-VI)

The ester (Ex. 21-V) was boiled with an excess of 1.5 eq. of hydrazine hydrate in ethanol for 4 h. After cooling, the crystals of the hydrazide (Ex. 21-VI) were boiled with water and dried. This gave 90%> of theory. Step 6: 2-(2, 6-Difluorophenyl)-2H-l ,2,3-triazole-4-carbonyl azide (Ex. 21-VII)

An aqueous solution of sodium nitrite was added to a suspension of the hydrazide (Ex. 21-VI) in 20%> strength aqueous hydrochloric acid. After further stirring at 10°C, the crystals of the acyl azide (Ex. 21- VII) were filtered off, washed with water and dried at room temperature under reduced pressure. This gave 75%) of theory. Step 7: 2-(2, 6-Difluorophenyl)-2H-l ,2,3-triazole-4-carbonyl isocyanate (Ex. 21-VIII)

The dried acyl azide (Ex. 21 -VII) was boiled in toluene until the evolution of gas had ended (about 2 h). The toluene was then removed on a rotary evaporator and the viscous residue of the isocyanate (Ex. 21- VIII) was directly reacted further without further purification. This gave about 90% of theory. Step 8: 2-(2, 6-Difluorophenyl)-2H-l,2,3-triazole-4-amine (Ex. 21 -IX)

The isocyanate (Ex. 21-VIII) was hydro lysed by 30 min of boiling in hydrochloric acid. Residual volatile substances were removed on a rotary evaporator, and the residue was treated with sodium carbonate solution. The precipitated crystals were filtered off, washed with water and recrystallized from hexane. This gave 70% of theory of the amine (Ex. 21 -IX). HPLC-MS: logP = 1.16; mass (m/z): 197.0 (M+H) + ; 'H-NMR (CD 3 CN) 5.46 (b, 2H), 7.33 - 7.38 (m, 3H), 7.56 - 7.64 (m, 1H).

N-[2-(2,6-Difluorophenyl)-2H-l,2,3-triazol-4-yl]-2-(trifl uoromethyl)benzamide (Compound 1-2-35 in Table 5)

Analogously to Synthesis Example 9 Step 2, 2-(2,6-difluorophenyl)-2H-l,2,3-triazole-4-amine (150 mg) was reacted with 2-(trifluoromethyl)benzoyl chloride (160 mg) and triethylamine (0.21 ml) in 3.9 ml of dichloromethane. Purification by column chromatography and preparative HPLC gave 143 mg of the title compound. HPLC-MS: logP = 2.80; mass (m/z): 369.1 (M+H) + ; 'H-NMR (CD 3 CN) 7.45 - 7.49 (m, 2H), 7.70 - 7.77 (m, 4H), 7.78 - 7.88 (m, 1H), 8.45 (s, 1H), 11.83 (s, 1H).

Synthesis Example 6: N-[l-(6-Chloro-5-cyano-3-fluoropyridin-2-yl)-lH-pyrazol-3-yl ]-2-(trifluoromethyl)benzamide

(Compound (1-1-606) in Table 1)

Analogously to Synthesis Example 25, Step 2, starting with 2,6-dichloro-5-fluoronicotinonitrile: HPLC- MS: logP = 2.94; mass (m/z): 410.0/411.9 (M+H) + ; IH-NMR (DMSO-D 6 ) 7.11 (m, 1H), 7.70 (m, 2H), 7.77 (m, 1H), 7.83 (m, 1H), 8.52 (m, 1H), 8.80 (m, 1H), 8.85 (m, 1H), 11.89 (s, 1H).

The compounds for the formulae (I-l), (1-4), (1-2), (1-5) and (1-3) described in Tables 1 to 5 are likewise preferred compounds which are used in experiments showing activity in controlling harmful microorganisms .

Table 1

The young plants of radish are treated by spraying the active ingredient prepared as described above. Control plants are treated only with an aqueous solution of acetone/Dimethyl sulfoxide/tween ® 80.

After 24 hours, the plants are contaminated by spraying the leaves with an aqueous suspension of Alternaria brassicae spores. The contaminated radish plants are incubated for 6 days at 20°C and at 100% relative humidity.

The test is evaluated 6 days after the inoculation. 0% means an efficacy which corresponds to that of the control plants while an efficacy of 100% means that no disease is observed.

In this test, under these conditions, at a concentration of 500 ppm of active ingredient, the following compounds according to the invention showed biological efficacy higher than or equal to 70%: 1-1-53; 1-1-164; 1-1-194; 1-1-209; 1-1-284; 1-1-479; 1-1-606; 1-2-1 ; 1-2-73; 1-2-79

Example 2: In vivo preventive test on Botrytis cinerea (grey mould)

The tested active ingredients are prepared by homogenization in a mixture of Acetone/Dimethyl sulfoxide/tween® 80, and then diluted with water to obtain the desired active material concentration.

The young plants of radish are treated by spraying the active ingredient prepared as described above. Control plants are treated only with an aqueous solution of acetone/Dimethyl sulfoxide/tween® 80.

After 24 hours, the plants are contaminated by spraying the leaves with an aqueous suspension of Botrytis cinerea spores. The contaminated gherkin plants are incubated for 4 to 5 days at 17°C and at 90%) relative humidity.

The test is evaluated 4 to 5 days after the inoculation. 0%> means an efficacy which corresponds to that of the control plants while an efficacy of 100%> means that no disease is observed.

In this test, under these conditions, at a concentration of 500 ppm of active ingredient, the following compounds according to the invention showed biological efficacy higher than or equal to 70%:

1-1-32; 1-1-49; 1-1-64; 1-1-65; 1-1-67; 1-1-70; 1-1-91 ; 1-1-99; 1-1-102; 1-1-108; 1-1-114; 1-1-118; 1-1-127; 1-1-145; 1-1-152; 1-1-164; 1-1-165; 1-1-183; 1-1-190; 1-1-191 ; 1-1-218; 1-1-219; 1-1-221 ; 1-1-248; 1-1- 277; 1-1-284; 1-1-358; 1-1-442; 1-1-479; 1-1-484; 1-1 -485; 1-1-487; 1-1-490; 1-1-491 ; 1-1-492; 1-1-494; I-

1- 501 ; 1-1-507; 1-1-558; 1-1-578; 1-1-581 ; 1-1-587; 1-1 -593; 1-1-596; 1-1-599; 1-1-606; 1-2-35; 1-2-36; I-

2- 37; 1-2-40; 1-2-41 ; 1-2-76; 1-2-79; 1-2-80; 1-3-7

Example 3 : In vivo preventive test on Puccinia recondita (brown rust on wheat) The tested active ingredients are prepared by homogenization in a mixture of Acetone/Dimethyl sulfoxide/tween® 80, and then diluted with water to obtain the desired active material concentration.

The young plants of radish are treated by spraying the active ingredient prepared as described above. Control plants are treated only with an aqueous solution of acetone/Dimethyl sulfoxide/tween® 80. After 24 hours, the plants are contaminated by spraying the leaves with an aqueous suspension of Puccinia recondita spores. The contaminated wheat plants are incubated for 24 hours at 20°C and at 100% relative humidity and then for 10 days at 20°C and at 70-80% relative humidity.

The test is evaluated 11 days after the inoculation. 0%> means an efficacy which corresponds to that of the control plants while an efficacy of 100%> means that no disease is observed. In this test, under these conditions, at a concentration of 500 ppm of active ingredient, the following compounds according to the invention showed biological efficacy higher than or equal to 70%:

1-1-5; 1-1-10; 1 1 11 ; 1-1-14; 1-1-32; 1-1-33; 1-1-34; 1-1 -41 ; 1-1-43; 1-1-44; 1-1-47; 1-1-48; 1-1-49; 1-1-52; 1-1-53; 1-1-65; 1-1 -66; 1-1-67; 1-1-69; 1-1-70; 1-1-78; 1-1-83; 1-1-96; 1-1-99; 1-1-100; 1-1-104; 1-1-105; I- 1-108; 1-1-113; 1-1-118; 1-1-123; 1-1-138; 1-1-145; 1-1-161 ; 1-1-165; 1-1-176; 1-1-183; 1-1-191 ; 1-1-192; 1-1-194; 1-1-195; 1-1-196; 1-1-218; 1-1-219; 1-1-221; 1-1-240; 1-1-248; 1-1-274; 1-1-275; 1-1-277; 1-1- 284; 1-1-285; 1-1-369; 1-1-370; 1-1-419; 1-1-507; 1-1-578; 1-1-581 ; 1-2-37; 1-2-40; 1-2-41 ; 1-2-73; 1-2-76; 1-2-79

Example 4: In vivo preventive test on Pyrenophora teres (net blotch on barley)

The tested active ingredients are prepared by homogenization in a mixture of Acetone/Dimethyl sulfoxide/tween® 80, and then diluted with water to obtain the desired active material concentration.

The young plants of radish are treated by spraying the active ingredient prepared as described above. Control plants are treated only with an aqueous solution of acetone/Dimethyl sulfoxide/tween® 80.

After 24 hours, the plants are contaminated by spraying the leaves with an aqueous suspension of Pyrenophora teres spores. The contaminated barley plants are incubated for 48 hours at 20°C and at 100%) relative humidity and then for 12 days at 20°C and at 70-80%) relative humidity.

The test is evaluated 14 days after the inoculation. 0%> means an efficacy which corresponds to that of the control plants while an efficacy of 100%> means that no disease is observed.

In this test, under these conditions, at a concentration of 500 ppm of active ingredient, the following compounds according to the invention showed biological efficacy higher than or equal to 70%: 1-1-65; 1-1-67; 1-1-83; 1-1-87; 1-1 -93; 1-1-99; 1-1-102; 1-1-104; 1-1-105; 1-1-118; 1-1-145; 1-1-148; 1-1- 156; 1-1-183; 1-1-191 ; 1-1-192; 1-1-194; 1-1-219; 1-1 -221 ; 1-1-240; 1-1-248; 1-1-276; 1-1-277; 1-1-284; I-

1- 566; 1-1-578; 1-1-581 ; 1-1-606; 1-2-14; 1-2-39; 1-2-40; 1-2-41 ; 1-2-50; 1-2-58; 1-2-62; 1-2-73; 1-2-76; I-

2- 78; 1-2-79; 1-2-82 Example 5: In vivo preventive test on Pyricularia oryzae (rice blast)

The tested active ingredients are prepared by homogenization in a mixture of Acetone/Dimethyl sulfoxide/tween® 80, and then diluted with water to obtain the desired active material concentration.

The young plants of radish are treated by spraying the active ingredient prepared as described above. Control plants are treated only with an aqueous solution of acetone/Dimethyl sulfoxide/tween® 80. After 24 hours, the plants are contaminated by spraying the leaves with an aqueous suspension of Pyricularia oryzae spores. The contaminated rice plants are incubated at 25°C and at 80% relative humidity.

The test is evaluated 6 days after the inoculation. 0%> means an efficacy which corresponds to that of the control plants while an efficacy of 100%> means that no disease is observed. In this test, under these conditions, at a concentration of 500 ppm of active ingredient, the following compounds according to the invention showed biological efficacy higher than or equal to 70%:

1-1-20; 1-1-114; 1-1-121 ; 1-1-123

Example 6: In vivo preventive test on Septoria tritici (leaf spot on wheat)

The tested active ingredients are prepared by homogenization in a mixture of Acetone/Dimethyl sulfoxide/tween® 80, and then diluted with water to obtain the desired active material concentration.

The young plants of radish are treated by spraying the active ingredient prepared as described above. Control plants are treated only with an aqueous solution of acetone/Dimethyl sulfoxide/tween® 80.

After 24 hours, the plants are contaminated by spraying the leaves with an aqueous suspension of Septoria tritici spores. The contaminated wheat plants are incubated for 72 hours at 18°C and at 100%) relative humidity and then for 21 days at 20°C and at 90% relative humidity.

The test is evaluated 24 days after the inoculation. 0% means an efficacy which corresponds to that of the control plants while an efficacy of 100% means that no disease is observed.

In this test, under these conditions, at a concentration of 500 ppm of active ingredient, the following compounds according to the invention showed biological efficacy higher than or equal to 70%: 1-1-20; 1-1-32; 1-1 -53; 1-1-60; 1-1-65; 1-1-66; 1-1-67; 1-1-69; 1-1-70; 1-1-99; 1-1-101 ; 1-1-104; 1-1-105; I- 1-107; 1-1-108; 1-1-110; 1-1-118; 1-1-121 ; 1-1-122; 1-1-123; 1-1-175; 1-1-183; 1-1-186; 1-1-195; 1-1-199; 1-1-218; 1-1-232; 1-1-240; 1-1-276; 1-1-281 ; 1-1-284; 1-1-288; 1-1-356; 1-1-366; 1-1-378; 1-1-433; 1-1- 435; 1-1-498; 1-1-581 ; 1-1-582; 1-1-596; 1-2-18; 1-2-40; 1-2-41 ; 1-2-50; 1-2-62; 1-2-73; 1-2-76; 1-2-79 In this test, under these conditions, at a concentration of 1200 g/ha of active ingredient, the following compounds according to the invention showed biological efficacy higher than or equal to 70%: 1-1-209

Example 7: in vivo preventive test on Sphaerotheca fuliginea (powdery mildew on cucurbits)

The tested active ingredients are prepared by homogenization in a mixture of Acetone/Dimethyl sulfoxide/tween® 80, and then diluted with water to obtain the desired active material concentration. The young plants of radish are treated by spraying the active ingredient prepared as described above. Control plants are treated only with an aqueous solution of acetone/Dimethyl sulfoxide/tween® 80.

After 24 hours, the plants are contaminated by spraying the leaves with an aqueous suspension of Sphaerotheca fuliginea spores. The contaminated gherkin plants are incubated for 72 hours at 18°C and at 100% relative humidity and then for 12 days at 20°C and at 70-80%) relative humidity. The test is evaluated 15 days after the inoculation. 0%> means an efficacy which corresponds to that of the control plants while an efficacy of 100%> means that no disease is observed.

In this test, under these conditions, at a concentration of 500 ppm of active ingredient, the following compounds according to the invention showed biological efficacy higher than or equal to 70%:

1-1-32; 1-1-65; 1-1-66; 1-1-67; 1-1 -96; 1-1-104; 1-1-183; 1-1-195; 1-1-218; 1-1-219; 1-1-232; 1-2-40; 1-2- 41 ; 1-2-79

Example 8: In vivo preventive test on Uromyces appendiculatus (bean rust)

The tested active ingredients are prepared by homogenization in a mixture of Acetone/Dimethyl sulfoxide/tween® 80, and then diluted with water to obtain the desired active material concentration.

The young plants of radish are treated by spraying the active ingredient prepared as described above. Control plants are treated only with an aqueous solution of acetone/Dimethyl sulfoxide/tween® 80.

After 24 hours, the plants are contaminated by spraying the leaves with an aqueous suspension of Uromyces appendiculatus spores. The contaminated bean plants are incubated for 24 hours at 20°C and at 100%) relative humidity and then for 10 days at 20°C and at 70-80%) relative humidity.

The test is evaluated 11 days after the inoculation. 0%> means an efficacy which corresponds to that of the control plants while an efficacy of 100% means that no disease is observed. In this test, under these conditions, at a concentration of 500 ppm of active ingredient, the following compounds according to the invention showed biological efficacy higher than or equal to 70%:

1 1 11 ; 1-1-33; 1-1-41 ; 1-1-43; 1-1-47; 1-1-48; 1-1-52; 1-1-53; 1-1-65; 1-1-67; 1-1-69; 1-1-70; 1-1-82; 1-1- 83; 1-1-96; 1-1-104; 1-1-108; 1-1-119; 1-1-123; 1-1 -196; 1-1-219; 1-1-248; 1-1-274; 1-1-275; 1-1 -277; 1-1- 284; 1-1-379; 1-1-593; 1-2-40; 1-2-41 ; 1-2-79

Example 9

Leptosphaeria test (wheat) / preventive

Solvent: 49 parts by weight of N,N-dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. To test for preventive activity, young plants are sprayed with a preparation of active compound at the stated rate of application. One day after this treatment, the plants are inoculated with an aqueous spore suspension of Leptosphaeria nodorum. The plants remain for 48 hours in an incubation cabinet at 22 °C and a relative atmospheric humidity of 100%. Then the plants are placed in a greenhouse at a temperature of approximately 22 °C and a relative atmospheric humidity of approximately 90%>. The test is evaluated 7-9 days after the inoculation. 0%> means an efficacy which corresponds to that of the untreated control, while an efficacy of 100%) means that no disease is observed. In this test, under these conditions, at a concentration of 500 ppm of active ingredient, the following compounds according to the invention showed biological efficacy higher than or equal to 70%:

1-1-33; 1-1-82; 1-1-118

Example 10

Pyricularia test (rice) / preventive Solvent: 49 parts by weight of N,N-dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. To test for preventive activity, young plants are sprayed with a preparation of active compound at the stated rate of application. One day after this treatment, the plants are inoculated with an aqueous spore suspension of Pyricularia oryzae. The plants remain for 48 hours in an incubation cabinet at 24 °C and a relative atmospheric humidity of 100%. Then the plants are placed in a greenhouse at a temperature of approximately 24 °C and a relative atmospheric humidity of approximately 80%. The test is evaluated 7 days after the inoculation. 0%> means an efficacy which corresponds to that of the untreated control, while an efficacy of 100%) means that no disease is observed.

In this test, under these conditions, at a concentration of 500 ppm of active ingredient, the following compounds according to the invention showed biological efficacy higher than or equal to 70%:

1-1-32; 1-1-51 ; 1-1-52; 1-1-211 ; 1-1-339 Example 11

Pyrenophora test (barley) / preventive

Solvent: 49 parts by weight of N,N-dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. To test for preventive activity, young plants are sprayed with the preparation of active compound at the stated rate of application. One day after this treatment, the plants are inoculated with an aqueous spore suspension of Pyrenophora teres. The plants remain for 48 hours in an incubation cabinet at 22 °C and a relative atmospheric humidity of 100%>. Then the plants are placed in a greenhouse at a temperature of approximately 20 °C and a relative atmospheric humidity of approximately 80%>. The test is evaluated 7-9 days after the inoculation. 0%> means an efficacy which corresponds to that of the untreated control while an efficacy of 100%> means that no disease is observed.

In this test, under these conditions, at a concentration of 500 ppm of active ingredient, the following compounds according to the invention showed biological efficacy higher than or equal to 70%: 1-1-2; 1-1-10; 1-1-19; 1-1-32; 1-1-33; 1-1-81 ; 1-1-82; 1-1-118; 1-1-119; 1-1-377; 1-1-413

Example 12

Leptosphaeria nodorum test (wheat) / preventive

Solvent: 49 parts by weight of N,N-dimethylacetamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, 1 part by weight of active compound or active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. To test for preventive activity, young plants are sprayed with the preparation of active compound or active compound combination at the stated rate of application. After the spray coating has been dried, the plants are sprayed with a spore suspension of Leptosphaeria nodorum. The plants remain for 48 hours in an incubation cabinet at approximately 20 °C and a relative atmospheric humidity of approximately 100%. The plants are placed in the greenhouse at a temperature of approximately 22 °C and a relative atmospheric humidity of approximately 80%. The test is evaluated 8 days after the inoculation. 0%> means an efficacy which corresponds to that of the untreated control, while an efficacy of 100%> means that no disease is observed.

In this test, under these conditions, at a concentration of 1000 ppm of active ingredient, the following compounds according to the invention showed biological efficacy higher than or equal to 70%:

1-1-75; 1-1-82; 1-1-284

Example 13 Puccinia triticina-test (wheat) / preventive

Solvent: 49 parts by weight of N,N-dimethylacetamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound or active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. To test for preventive activity, young plants are sprayed with the preparation of active compound or active compound combination at the stated rate of application. After the spray coating has been dried, the plants are sprayed with a spore suspension of Puccinia triticina. The plants remain for 48 hours in an incubation cabinet at approximately 20 °C and a relative atmospheric humidity of approximately 100%). The plants are placed in the greenhouse at a temperature of approximately 20 °C and a relative atmospheric humidity of approximately 80%>. The test is evaluated 8 days after the inoculation. 0%> means an efficacy which corresponds to that of the untreated control, while an efficacy of 100%> means that no disease is observed.

In this test, under these conditions, at a concentration of 1000 ppm of active ingredient, the following compounds according to the invention showed biological efficacy higher than or equal to 70%: 1-1-33; 1-1-82; 1-1-118; 1-1-119; 1-1-140 Example 14

Pyrenophora teres-test (barley) / preventive

Solvent: 49 parts by weight of N,N-dimethylacetamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, 1 part by weight of active compound or active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. To test for preventive activity, young plants are sprayed with the preparation of active compound or active compound combination at the stated rate of application. After the spray coating has been dried, the plants are sprayed with a spore suspension of Pyrenophora teres. The plants remain for 48 hours in an incubation cabinet at approximately 20 °C and a relative atmospheric humidity of approximately 100%. The plants are placed in the greenhouse at a temperature of approximately 20 °C and a relative atmospheric humidity of approximately 80%. The test is evaluated 8 days after the inoculation. 0%> means an efficacy which corresponds to that of the untreated control, while an efficacy of 100%> means that no disease is observed. In this test, under these conditions, at a concentration of 1000 ppm of active ingredient, the following compounds according to the invention showed biological efficacy higher than or equal to 70%:

1-1-33; 1-1-75; 1-1-119; 1-1-140; 1-1-284; 1-2-35

Example 15

Pyricularia oryzae-test (rice) / preventive Solvent: 49 parts by weight of N,N-dimethylacetamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound or active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. To test for preventive activity, young plants are sprayed with the preparation of active compound or active compound combination at the stated rate of application. After the spray coating has been dried, the plants are sprayed with a spore suspension of Pyricularia oryzae. The plants remain for 25 hours in an incubation cabinet at approximately 25°C and a relative atmospheric humidity of approximately 100%. The plants are placed in the greenhouse under a translucent incubations cabinet at a temperature of approximately 25°C and a relative atmospheric humidity of approximately 100%). The test is evaluated 8 days after the inoculation. 0%> means an efficacy which corresponds to that of the control, while an efficacy of 100% means that no disease is observed.

In this test, under these conditions, at a concentration of 1000 ppm of active ingredient, the following compounds according to the invention showed biological efficacy higher than or equal to 70%: 1-1-75; 1-1-284

Example 16

Septoria tritici-test (wheat) / preventive

Solvent: 49 parts by weight of N,N-dimethylacetamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, 1 part by weight of active compound or active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. To test for preventive activity, young plants are sprayed with the preparation of active compound or active compound combination at the stated rate of application. After the spray coating has been dried, the plants are sprayed with a spore suspension of Septoria tritici. The plants remain for 48 hours in an incubation cabinet at approximately 20 °C and a relative atmospheric humidity of approximately 100%> and afterwards for 60 hours at approximately 15 °C in a translucent incubation cabinet at a relative atmospheric humidity of approximately 100%>. The plants are placed in the greenhouse at a temperature of approximately 15 °C and a relative atmospheric humidity of approximately 80%>. The test is evaluated 21 days after the inoculation. 0%> means an efficacy which corresponds to that of the untreated control, while an efficacy of 100%) means that no disease is observed.

In this test, under these conditions, at a concentration of 1000 ppm of active ingredient, the following compounds according to the invention showed biological efficacy higher than or equal to 70%:

1-1-140; 1-1-284; 1-2-35 Example 17

Phakopsora test (soybeans) / preventive

Solvent: 24.5 parts by weight of acetone parts by weight of dimethylacetamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. To test for preventive activity, young plants are sprayed with the preparation of active compound at the stated rate of application. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of the causal agent of soybean rust (Phakopsora pachyrhizi) and stay for 24h without light in an incubation cabinet at approximately 24°C and a relative atmospheric humidity of 95 %>. The plants remain in the incubation cabinet at approximately 24°C and a relative atmospheric humidity of approximately 80 % and a day / night interval of 12h. The test is evaluated 7 days after the inoculation. 0% means an efficacy which corresponds to that of the untreated control, while an efficacy of 100% means that no disease is observed.

In this test, under these conditions, at a concentration of 10 ppm of active ingredient, the following compounds according to the invention showed biological efficacy higher than or equal to 70%:

1-1-248

Example 18 Venturia test (apples) / preventive

Solvent: 24.5 parts by weight of acetone

24.5 parts by weight of dimethylacetamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. To test for preventive activity, young plants are sprayed with the preparation of active compound at the stated rate of application. After the spray coating has dried on, the plants are inoculated with an aqueous conidia suspension of the causal agent of apple scab (Venturia inaequalis) and then remain for 1 day in an incubation cabinet at approximately 20 °C and a relative atmospheric humidity of 100%). The plants are then placed in a greenhouse at approximately 21 °C and a relative atmospheric humidity of approximately 90%>. The test is evaluated 10 days after the inoculation. 0%> means an efficacy which corresponds to that of the untreated control, while an efficacy of 100%> means that no disease is observed.

In this test, under these conditions, at a concentration of 100 ppm of active ingredient, the following compounds according to the invention showed biological efficacy higher than or equal to 70%:

1-1-75; 1-1-140; 1-1-284; 1-2-35