WO2013135672A1 - Fungicidal pyrimidine compounds - Google Patents

Fungicidal pyrimidine compounds Download PDF

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WO2013135672A1
WO2013135672A1 PCT/EP2013/054967 EP2013054967W WO2013135672A1 WO 2013135672 A1 WO2013135672 A1 WO 2013135672A1 EP 2013054967 W EP2013054967 W EP 2013054967W WO 2013135672 A1 WO2013135672 A1 WO 2013135672A1
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Prior art keywords
ci
c4
alkyl
yl
individualized compound
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PCT/EP2013/054967
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French (fr)
Inventor
Wassilios Grammenos
Ian Robert CRAIG
Nadege Boudet
Bernd Müller
Jochen Dietz
Erica May Wilson LAUTERWASSER
Jan Klaas Lohmann
Jurith Montag
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Basf Se
Basf Schweiz Ag
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Priority to EP12159325.5 priority
Priority to US61/610,024 priority
Priority to EP12159325 priority
Priority to EP12165104.6 priority
Priority to EP12165104 priority
Application filed by Basf Se, Basf Schweiz Ag filed Critical Basf Se
Publication of WO2013135672A1 publication Critical patent/WO2013135672A1/en

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES, AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/541,3-Diazines; Hydrogenated 1,3-diazines

Abstract

The present invention relates to fungicidal pyrimidine compounds, to their use and to methods for combating phytopathogenic fungi. The present invention also relates to seeds treated with at least one such compound. Furthermore the invention relates to processes for preparing compounds of formula I.

Description

Fungicidal pyrimidine compounds

Description The present invention relates to fungicidal pyrimidine compounds, to their use and to methods for combating phytopathogenic fungi. The present invention also relates to seeds treated with at least one such compound. Furthermore the invention relates to processes for preparing compounds of formula I. EP 51921 1 A1 discloses 4-aminopyrimidines for use as insecticides and fungicides.

EP 331529 A2 and JP 05105671 A describe 4-aminopyrmidines as insecticides.

EP 527016 A1 discloses N-(4 pyrimidinyl)amides as herbicides. The compounds according to the present invention differ from those described in the abovementioned publications in that the terminal ring is always a non-condensed heterocycle (Het).

WO 201 1025505 relates to 1 - or 2-(4-(aryloxy)-phenyl)ethylamino-, oxy- or sulfanyl)pteridines and 1 - or 2-(4-(heteroaryloxy)-phenyl)ethylamino-, oxy- or sulfanyl)pteridines and their use as agrochemicals and animal health products.

WO 201 1085084 relates to thiazolo[5,4-d]pyrimidines and their use as agrochemicals.

The compounds according to the present invention differ from those described in the

abovementioned publications in that it relates to substituted pyrimidines wherein an

ethanolamine group is inserted between the pyrimidine ring and the phenyl ring instead of an ethylamino group and that it refers to non-fused 4-aminopyrimidines.

WO 2002/22584 relates to certain thrombin inhibitors and discloses N-[2-[3-(1 -isobutyltetrazol- 5-yl)-5-methyl-phenoxy]-1 -methyl-ethyl]pyrimidin-4-amine.

In many cases, in particular at low application rates, the fungicidal activity of known fungicidal compounds is unsatisfactory. Based on this, it was an object of the present invention to provide compounds having improved activity and/or a broader activity spectrum against

phytopathogenic fungi. This objective is achieved by the use of substituted pyrimidine compounds of formula I having good fungicidal activity against phytopathogenic harmful fungi.

Accordingly, the present in rmula I

Figure imgf000002_0001

wherein:

Ra2, Ra5, Ra6 independently of each other are hydrogen, halogen, CN, N02, OH, SH, Ci-C4- alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, C 1 -C4-a I ky I s u If i ny I , Ci-C4-haloalkylsulfinyl, Ci-C4-alkylsulfonyl, Ci-C4-haloalkylsulfonyl, Ci- C4-a I koxy-C 1 -C4-a I ky I , C 1 -C4-a I koxy-

Ci-C4-alkoxy, C2-C4-alkenyl, C2-C4-alkynyl, C2-C4-haloalkenyl, C2-C4-haloalkynyl, C3-C8- cycloalkyl, C3-C8-cycloalkyloxy, C3-C8-cycloalkyl-Ci-C4-alkyl, NRARB, C(=0)R',

C(=NOR")R"' or -C(=NH)-0-R"';

RA, RB independently of one another are hydrogen, Ci-C4-alkyl, C2-C4- alkenyl, C2-C4-alkynyl, phenyl, benzyl, Cs-Cs-cycloalkyl, Cs-Cs-cycloalkenyl or - (C=0)-R';

R' is hydrogen, OH, NH2, Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, C2-C4-alkynyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylamino or di(Ci-C4-alkyl)amino;

R" is hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, C2-C4-alkynyl or

C 1 -C4-a I koxy-C 1 -C4-a I ky I ,

R'" is hydrogen or Ci-C4-alkyl; is hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkoxy- Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, CN, CH2CN, NRARB or

CH2-0-C(=0)R';

, R2 independently of each other are hydrogen, CN , Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl, C2-C4- alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, Cs-Cs-cycloalkyl, C3-C8- cycloalkyl-Ci-C4-alkyl, C3-C8-cycloalkyloxy, NRARB, C(=0)R', C(=NOR")R"', -C(=NH)-0-R"' or benzyl wherein the phenyl moiety of benzyl is unsubstituted or carries 1 , 2 , 3, 4, or 5 substituents selected from the group consisting of CN, halogen, Ci-C4-alkyl, Ci-C4-ha- loalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, (Ci-C4-alkoxy)carbonyl and di(Ci-C4-alkyl)amino- carbonyl; or two radicals R1 and R2 that are bound to the same carbon atom form together with said carbon atom a saturated or partially unsaturated

3-, 4-, 5-, 6-, or 7-membered carbocycle or a saturated or partially unsaturated 3-, 4-, 5-, 6-, or 7-membered heterocycle, wherein the ring member atoms of the abovementioned heterocycle include beside carbon atoms 1 , 2, 3 or 4 heteroatoms selected from the group of N, O and S, and wherein the abovementioned cycle is unsubstituted or carries 1 , 2, 3 or 4 substituents selected from halogen, CN, OH, SH, Ci-C4-alkyl, Ci-C4-alkoxy or C1-C4- alkylthio; and one or two CH2 groups of the abovementioned cycles may be respectively be replaced by one or two C(=0) or C(=S) groups; is a divalent group selected from -CR3R4-, -C(=0)-, -C(=S)-, -C(=NRD)- and -C(=NORD)-, wherein

RD is hydrogen or Ci-C4-alkyl, and wherein

R3 and R4 independently of each other are hydrogen, CN, Ci-C4-hydroxyalkyl, C1-C4- alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4- haloalkynyl, Cs-Cs-cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl, Cs-Cs-cycloalkyloxy, C(=0)R\ C(=NOR")R"',-C(=NH)-0-R"' or benzyl wherein the phenyl moiety of benzyl is unsubstituted or carries 1 , 2 , 3, 4, or 5 substituents selected from the group consisting of CN, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, C1-C4- haloalkoxy, (Ci-C4-alkoxy)carbonyl and di(Ci-C4-alkyl)aminocarbonyl, or two radicals R3 and R4 that are bound to the same carbon atom form together with said carbon atom a saturated or partially unsaturated

3-, 4-, 5-, 6-, or 7-membered carbocycle or a saturated or partially unsaturated 3-, 4- , 5-, 6-, or 7-membered heterocycle, wherein the ring member atoms of the abovementioned heterocycle include beside carbon atoms 1 , 2, 3 or 4 heteroatoms selected from the group of N, O and S, and wherein the abovementioned cycle is unsubstituted or carries 1 , 2, 3 or 4 substituents selected from halogen, CN, OH, SH, Ci-C4-alkyl, Ci-C4-alkoxy or Ci-C4-alkylthio; and one or two CH2 groups of the abovementioned cycles may be respectively replaced by one or two C(=0) or C(=S) groups; indicates the number of substituents Rb on the phenyl ring and n is 0, 1 , 2, 3 or 4; is halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, NRARB, C(=0)R', C(=NOR")R"' or -C(=NH)-0-R"', it being possible for n = 2, 3 or 4 that Rb are identical or different; is oxygen or a direct bond between Het and the phenyl ring; is a 5- or 6-membered heteroaryl, wherein the ring member atoms of the heteroaryl include besides carbon atoms 1 , 2, 3 or 4 heteroatoms selected from the group of N, O and S and wherein the heteroaryl is unsubstituted or carries 1 , 2, 3 or 4 identical or different groups Rc:

Rc is halogen, CN, N02, NH2, Ci-C6-alkyl, d-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-halo- alkoxy, Ci-C6-alkylamino, di(Ci-C6-alkyl)amino, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfinyl, Ci-C6-haloalkylsulfinyl, Ci-C6-alkylsulfonyl,

Ci-C6-haloalkylsulfonyl, Ci-C6-alkoxy-Ci-C4-alkyl, Ci-C6-haloalkoxy-Ci-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C(=0)R', C(=NOR")R"', C3-C8-cycloalkyl, C3-C8- cycloalkyl-Ci-C4-alkyl, phenyl, phenoxy, phenoxy-Ci-C4-alkyl or a 5- or 6-membered heteroaryl, wherein the ring member atoms of the heteroaryl include besides carbon atoms 1 , 2, 3 or 4 heteroatoms selected from the group of N, O and S, and wherein the aforementioned cyclic radicals are unsubstituted or carry 1 , 2, 3 or 4 identical or different substituents Rd:

Rd is halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy or Ci-C4-haloalkoxy; and the N-oxides and the agriculturally acceptable salts of the compounds of formula I, with the provision that N-[2-[3-(1 -isobutyltetrazol-5-yl)-5-methyl-phenoxy]-1 -methyl-ethyl]pyrimidin-4- amine be excluded.

The present invention furthermore relates to processes for preparing compounds of formula I. The present invention furthermore relates to intermediates such as compounds of formulae III, lla and Ilia and to processes for preparing them. Accordingly a 4-halopyrimidine compound II, wherein Hal is halogen, preferably CI or F, can be reacted with a suitable amine compound III, wherein X is -CR3R4-, to obtain a compound I according to the present invention, wherein X is - CR3R4-, as shown in Scheme 1 :

Scheme 1 solvent, base

and/or catalyst

Figure imgf000005_0001
Generally, this reaction is carried out at temperatures of from 0 to 200°C, preferably from 50 to 170°C, preferably in an inert organic solvent and preferably in presence of a base or a catalyst or a combination of a base and a catalyst.

Suitable catalysts are e.g. haldies such as NaF, KF, LiF, NaBr, KBr, LiBr, Nal, Kl, Lil; ionic liquids, such as imidazolium catalysts; transition metal catalysts like palladium, rhodium, ruthenium, iron, copper in the form of halides, pseudohalides, alkoxides, carboxylates

(pre-ferred acetate), complexes with dibenzylidene acetone and ligands like phosphine, phos- hites, phosphoramidate ligands. Preferred ligands are bidentate and sterically demanding phosphorous ligands, even more preferably the catalysts are selected from 2,2' bis(dipheny phosphanyl)-1 ,1 '-binaphthyl, 2,2'-Bis(diphenylphosphino)-1 ,1 '-biphenyl, 2, 4', 6'- diisopropyl-1 ,1 '-biphenyl-2-yldicyclohexylphosphine, 2-(dicyclohexylphosphino)-2',6' dimethoxy- 1 ,1 ' b phenyl, 1 ,1 -bis(diphenylphosphino)ferrocene, 9,9-dimethyl-4,5

bis(diphenylphosphino)^xan^thene, 1 ,2-bis(diphenylphosphino)ethane (dppe), 1 ,3- propanediylbis[diphenylphosphine], 1 ,4 butanediylbis[diphenylphosphine] and 1 ,1 '-(1 ,2- ethanediyl)bis[1 -(2-methoxyphenyl)-1 phenyl-diposphine.

Suitable solvents are aromatic hydrocarbons such as toluene, o-, m- and p-xylene; halogenated hydro-carbons chlorobenzene, dichlorobenzene; ethers such as dioxane, anisole and THF; nitriles such as acetonitrile and propionitrile; ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert. -butyl methyl ketone; alcohols such as ethanol, n-propanol, isopropanol, n-butanol and tert.-butanol; and also DMSO, DMF, dimethyl acetamide, NMP, NEP and acetic acid ethyl ester, preferably THF, DMSO, DMF, dimethyl acetamide, NMP or NEP; even more preferably THF, DMF or NMP. It is also possible to use mixtures of the solvents mentioned.

Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide; alkali metal and alkaline earth metal oxides such as lithium oxide, sodium oxide, potassium oxide and calcium oxide; alkali metal and alkaline earth metal phosphates such as lithium phosphate, sodium phosphate, potassium phosphate and calcium phosphate; alkali metal amides such as lithium amide, sodium amide and potassium amide; alkali metal and alkaline earth metal hydrides lithium hydride, sodium hydride, potassium hydride and calcium hydride; alkali metal and alkaline earth metal carbonates such as lithium carbonate, potassium carbonate and calcium carbonate, caesium carbonate; moreover organic bases, for example tertiary amines such as trimethyl-amine (TMA), triethylamine (TEA), tributylamine (TBA), diisopropylethylamine (DIPEA) and N-methyl-2-pyrrolidone (NMP), pyridine, substituted pyridines such as collidine, lutidine and 4 dimethylaminopyridine (DMAP), and also bicyclic amines. Preference is given to sodium hydride, potassium hydride, lithium carbonate, potassium carbonate, caesium carbonate, TEA, TBA and DIPEA, in particular DIPEA. The bases are generally employed in equimolar amounts, in excess or, if appropriate, as solvent. The amount of base is typically 1.1 to 5.0 molar equivalents relative to 1 mole of compounds II.

The starting materials are generally reacted with one another in equimolar amounts. In terms of yields, it may be advantageous to employ an excess of compounds III, based on 1.1 to 2.5 equivalents, preferred 1 .1 to 1.5 equivalents of compounds II.

The compounds II are known from the literature or are commercially available or they can be prepared for example in analogy to methods described in: Heterocycles (2009) 78(7), 1627- 1665; New J. Chem. (1994) 18(6), 701 -8; WO 2005/095357; Science of Synthesis (2004) 16, 379-572;WO 2008/156726; WO 2006/072831 ; Organic Reactions (Hoboken, NJ, United States) (2000), 56; or Targets in Heterocyclic Systems (2008) 12, 59-84.

The phenethanol amine compounds III are known from the literature or are commercially available or they can be prepared for example in analogy to methods described in:

WO 201 1/085084 A1 or WO 201 1/025505 A1 . Alternatively, compounds III can be prepared by way of a nucleophilic substitution, aziridine opening, or a Mitsunobu reaction of the phenol Het- AD according to the general reaction in scheme 2 according to the literature precedents Journal of Medicinal Chemistry (2003), 46(10), 1845-1857, Journal of Medicinal Chemistry (201 1 ),54(5), 1276-1287, Bioorganic & Medicinal Chemistry Letters (201 1 ), 21 (22), 6674-6677; Tetrahedron (2009), 65(45), 9494-9504; Tetrahedron Letters (201 1 ), 52(17), 2136-2139, Journal of Organic Chemistry (201 1 ), 76(5), 1475-1478; Journal of Organic Chemistry (201 1 ), 76(5), 1475-1478; Tetrahedron Asymmetry (2007), 18(20), 2409-2417; and wherein PG in compounds AD-1 stands for an appropriate protecting group of the amine, and LG in compounds AD-2 is a suitable leaving group such as fluorine, chlorine, bromine, iodine or an alkylsulfonate, for example, methylsulfonate, trifluoromethylsulfonate or an arylsulfonate such as, for example, tosylate.

Scheme 2

Figure imgf000007_0001

PPh3, DEAD

The compound Het-AD can be prepared as described in WO 201 1/085084 A1 or

WO 201 1/025505 A1 or by way of either a Baeyer-Villiger reaction with an appropriately decorated aryl ketone followed by hydrolysis of the resultant ester as exemplified in Chemistry- A European Journal (2008), 14(30), 9330-9337 or Synlett (201 1 ), (15), 2245-2247, or by an aromatic nucleophilic substitution reaction of the requisite benzene ring bearing a leaving group as found in Catalysis Communications (201 1 ), 12(15), 1463-1465 or in European Journal of Organic Chemistry (201 1 ), 201 1 (36), 7288-7293 according to the general reaction scheme 3.

Scheme 3

Figure imgf000007_0002
When Y is O, then Het-AD can be synthesized according to scheme 4. Compound AD-3, in which the phenyl ring bears a hydroxyl group in meta- or para-position, is reacted with a heterocycle Het-LG, in which LG is a leaving group such as, e.g. F or CI, in the presence of a base and/or a catalyst. Or compound AD-4, in which LG is a leaving group in para-position such as, for example, F or CI, is reacted with a hydroxyl-heterocycle HO-Het in the presence of a base and/or a catalyst according to procedures described in WO 201 1032277 A1 , WO

2008065393 A1 ,

WO 2007096647 A2, WO 2007006714 A1 , AU 2006201959 A1 , DE 19518073 A1 (with catalyst: Organic Letters (2001 ), 3(26), 4315-4317; Journal of the American Chemical Society (1999), 121 (18), 4369-4378) and provides Het-AD.

Scheme 4

H

Figure imgf000008_0001

AD-3 AD-4

+ +

Het— LG H O— Het

For In compounds I wherein Y is a direct bond, Het-AD can be synthesized by standard metal mediated coupling reaction of AD-5, wherein T is a suitable coupling partner such as, chlorine, bromine, iodine or an alkylsulfonate, for example, trifluoromethylsulfonate and Het-LG in Scheme 5 as illustrated in Dalton Transactions (201 1 ), 40(47), 12676-12689, Bioorganic & Medicinal Chemistry Letters (201 1 ), 21 (21 ), 6366-6369, US 201 10257402 A1 or WO

201 1053559A1 .

Scheme 5 t bond

Figure imgf000008_0002

AD-5

Compounds I in which X is -CH(C(=0)0-Ci-C4-alkyl)-, -CH(C(=0)NH2)-,

-CH(C(=0)OH)- or -CHCN- can be prepared as follows or pursuing analogous proced outlined in scheme 6: Scheme 6

Figure imgf000009_0001

The orthogonally protected serine derivative AD-12 can be transformed to the corresponding biaryl ether AD-13 with suitable heteroaromatic groups Het-LG as described in scheme 6. The coupling of AD-13 with 4-halopyrimidine compound II can be performed in analogy to Journal of Medicinal Chemistry (201 1 ), 54(15), 5335-5348, Bioorganic & Medicinal Chemistry Letters (201 1 ), 21 (6), 1741 -1743, US 20100068197 A1 , WO 2005000246 A2, which leads to the formation of compounds I with Q being Ci-C4-alkoxy (X is -CH(C(=0)-Ci-C4-alkoxy)-).

Saponificaton of the ester group with hydroxide bases leads to acid compounds I wherein X is -CH(C(=0)OH)-. Aminolysis of the ester group with ammonia and a catalyst (e.g. potassium cyanide) yields compounds I wherein X is -CH(C(=0)NH2)-. Dehydratisation of the amide using POC or trifluoro acetic acid anhydride with pyridine or treatment with other reagents capable to dehydrate a carboxamide such as, e.g., Burgess's reagent, leads to compound I, in which X is - CHCN- as described in WO 2006098961 A2.

Compounds I in which R1 is -C(=0)0-Ci-C4-alkyl-, -C(=0)NH2-, -C(=0)OH- or -CN- and X is a carbon with sp3-hybridization can be prepared according to scheme 6 by employing the appropriately substituted commercially available or literature-known 3-amino-2- hydroxypropanoate. Compounds I in which R1 is -C(=0)0-Ci-C4-alkyl, -C(=0)NH2, -C(=0)OH or -CN and X is -C(=0)- can also be prepared according to scheme 7. The chemistries in scheme 7 are analogous to scheme 6, employing 2-hydroxy-dimethylmalonate as starting material and enacting an amide type coupling as described later for the amide class in general. Scheme 7

Figure imgf000010_0001

Likewise, a 4-halopyrimidine compound II, wherein Hal is halogen, preferably CI or F, can be reacted with a suitable amide compound III, wherein X is -C(=0)- to obtain a compound I wherein X is -C(=0)- as shown in scheme 1 .

Generally, this reaction is carried out at temperatures of from 0 to 200°C, preferably from 50 to 170°C, in an inert organic solvent preferably in the presence of a base or a catalyst or a combination of a base and a catalyst in a solvent. Suitable catalysts are e.g. halides such as NaF, KF, LiF, NaBr, KBr, LiBr, Nal, Kl, Lil; ionic liquids, such as imidazolium catalysts; transition metal catalysts like palladium, rhodium, ruthenium, iron, copper in the form of halides, pseudohalides, alkoxides, carboxylates (preferred acetate), complexes with dibenzylidene acetone and ligands like phosphine, phosphites, phosphoramidate ligands. Preferred ligands are bidentate and sterically demanding

phosphorous ligands, even more preferably the catalysts are selected from 2,2'-bis(diphenyl- phosphanyl)-1 ,1 '-binaphthyl, 2,2'-bis(diphenylphosphino)-1 ,1 '-biphenyl, 2,4',6'-diisopropyl-1 ,1 '- biphenyl-2-yldicyclohexylphosphine, 2-(dicyclohexylphosphino)-2',6'-dimethoxy-1 ,1 '-biphenyl, 1 ,1 -bis(diphenylphosphino)ferrocene, 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene, 1 ,2-bis(diphenylphosphino)ethane (dppe), 1 ,3-propanediylbis[diphenylphosphine],

1 ,4-butanediylbis[diphenylphosphine] and 1 ,1 '-(1 ,2-ethanediyl)bis[1 -(2-methoxyphenyl)- 1 -phenyl-diposphine.

Suitable solvents are aromatic hydrocarbons such as toluene, o-, m- and p-xylene; halogenated hydrocarbons such as chlorobenzene, dichlorobenzene; ethers such as dioxane, anisole and THF; nitriles such as acetonitrile and propionitrile; ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert. -butyl methyl ketone; alcohols such as ethanol, n-propanol, isopropanol, n-butanol and tert.-butanol; and also DMSO, DMF, dimethyl acetamide, NMP, NEP and acetic acid ethyl ester. Preferably THF, DMSO, DMF, dimethyl acetamide, NMP or NEP are used; even more preferably THF, DMF or NMP are used. It is also possible to use mixtures of the solvents mentioned.

Suitable bases and their amounts are as described for the reaction with a phenethanol amine compound III, wherein X is -CR3R4-, as described above. The starting materials, are generally reacted with one another in equimolar amounts. In terms of yields, it may be advantageous to employ an excess of compounds III, based on 1.1 to 2.5 equivalents, preferred 1.1 to 1 .5 equivalents of compounds II.

The amide compounds III are known from the literature or are commercially available or they can be prepared for example in analogy to methods described in

US 201 10135650 A1 , WO 20101 10907 A1 , US 201 10178107 A1 , or Bioorganic & Medicinal Chemistry (201 1 ), 19(15),4482-4498, Journal of the American Chemical Society (201 1 ), 133(13), 4924-4929, Tetrahedron Letters (201 1 ), 52(7), 757-760.

Alternatively, amide compounds I, wherein X is -C(=0)-, can be synthesized by reacting

4-amino-pyrimidine compounds Ila [available by reaction of a chloropyrimidine II with excess of ammonia in analogy to methods described in WO 201 1 147066, WO 2006135719,

US 20050245530 A1 , J. Chem. Soc. (1951 ), 3439-44; Helv. Chim. Act. (1951 ), 34, 835-40] with compounds of the formula Ilia in which Z is hydrogen or Ci-C4-alkyl, preferably in the presence of AIMe3 (1 to 3 equivalents) as stoichiometric reagent, preferably in an inert organic solvent such as toluene (in analogy to US 20100063063 A1 ; WO 200501 1601 A2; WO 2006074884 A1 ) as outlined in scheme 8.

Scheme 8

Figure imgf000011_0001

lla Ilia

Compounds Ilia are either known in the literature, are commercially available, or can be synthesized by the reaction of the appropriate alpha chloro ester or alpha hydroxyl ester and Het-AD according to WO201 1046569 A1 , Journal of Heterocyclic Chemistry (2010), 47(6), 1310-1316, European Journal of Medicinal Chemistry (201 1 ), 46(9), 3639-3650 or WO

201 1 100838A1 . As another alternative, amide compounds I, wherein X is -C(=0)-, can be synthesized by reacting 4-amino-pyrimidine compounds Ila with the acid chloride of compound Ilia according to standard methods. The acid chlorides of compound Ilia are either known in the literature, commercially available or derived from Ilia through standard chemistries.

Compounds I , wherein X is -C(=S)-, can be prepared for example in analogy to methods described in US20100022538 A1 , J. Med. Chem. (201 1 ), 54(9), 3241 -3250, J. Org. Chem. (201 1 ), 76(6), 1546-1553, Org. Lett. (2010), 12(23), 5570-5572.

Compounds I, wherein X is -C(=NRD)-, can be prepared from compounds I, wherein X is -C(=0)-, in analogy to Bioorg. Med. Chem. (2008) 16(8), 4600-4616, J. Med. Chem. (2004) 47(3), 663-672, Eur. J. Org. Chem. (2004) 5, 1025-1032, J. Med. Chem. (1987) 30(4), 720-1 .

Compounds I, wherein X is -C(=NORD)-, can be prepared from compounds I, wherein X is

-C(=0)-, in analogy to WO 2007/075598 or from compounds I, wherein X is

-C(=S)- , according to WO 2008/039520 and O'zbekiston Kimyo Jurnali (2004) 4, 3-6.

Compounds I and intermediates, wherein R is hydrogen, can be converted by conventional processes such as alkylation. Examples of suitable alkylating agents include alkyl halides, such as alkyl chloride, alkyl bromide or alkyl iodide, examples being methyl chloride, methyl bromide or methyl iodide, or dialkyl sulfates such as dimethyl sulfate or diethyl sulfate. The reaction with the alkylating agent is carried out advantageously in the presence of a solvent. Solvents used for these reactions are - depending on temperature range - aliphatic, cycloaliphatic or aromatic hydrocarbons such as hexane, cyclohexane, toluene, xylene, chlorinated aliphatic and aromatic hydrocarbons such as DCM, chlorobenzene, open-chain dialkyl ethers such as diethyl ether, di- n-propyl ether, MTBE, cyclic ethers such as THF, 1 ,4-dioxane, glycol ethers such as dimethyl glycol ether, and also DMSO, DMF, dimethyl acetamide, NMP, NEP and acetic acid ethyl ester, preferably DMF, DMSO, NMP or NEP, or mixtures of these solvents.

If individual compounds I cannot be obtained by the routes described above, they can be prepared by derivatization of other compounds I. The N-oxides may be prepared from the compounds I according to conventional oxidation methods, e. g. by treating compounds I with an organic peracid such as metachloroperbenzoic acid (cf. WO 03/64572 or J. Med. Chem. (1995), 38(1 1 ), 1892-1903,); or with inorganic oxidizing agents such as hydrogen peroxide (cf. J. Heterocyc. Chem. (1981 ), 18 (7), 1305-1308) or oxone (cf. J. Am. Chem. Soc. (2001 ), 123 (25), 5962-5973). The oxidation may lead to pure mono-N-oxides or to a mixture of different N- oxides, which can be separated by conventional methods such as chromatography.

If the synthesis yields mixtures of isomers, a separation is generally not necessarily required since in some cases the individual isomers can be interconverted during work-up for use or during application (e. g. under the action of light, acids or bases). Such conversions may also take place after use, e. g. in the treatment of plants in the treated plant, or in the harmful fungus to be controlled. The reaction mixtures are worked up in a customary manner, for example by mixing with water, separating the phases and, if appropriate, chromatic purification of the crude products. In some cases, the intermediates and end products are obtained in the form of colorless or slightly viscous oils which can be freed from volatile components or purified under reduced pressure and at moderately elevated temperatures. If the intermediates and end products are obtained as solids, purification can also be carried out by recrystallization or digestion.

The compounds of the present invention are useful for combating harmful fungi. Therefore the present invention furthermore relates to a method for combating harmful fungi, which process comprises treating the fungi or the materials, plants, the soil or seeds to be protected against fungal attack, with an effective amount of at least one compound of formula I or of an N-oxide or an agriculturally acceptable salt thereof.

Furthermore, the present invention also relates to seed comprising a compound of formula I, or an N-oxide or an agriculturally acceptable salt thereof, in an amount of from 0.1 g to 10 kg per 100 kg of seed.

Agriculturally useful salts of the compounds I encompass especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the fungicidal action of the compounds I. Suitable cations are thus in particular the ions of the alkali metals, preferably sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, of the transition metals, preferably manganese, copper, zinc and iron, and also the ammonium ion which, if desired, may carry one to four Ci-C4-alkyl substituents and/or one phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore

phosphonium ions, sulfonium ions, preferably tri(Ci-C4-alkyl)sulfonium, and sulfoxonium ions, preferably tri(Ci-C4-alkyl)sulfoxonium.

Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogensulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of Ci-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting a compound I with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.

Depending on the substitution pattern, the compounds of formula I and their N-oxides may have one or more centers of chirality, in which case they are present as pure enantiomers or pure diastereomers or as enantiomer or diastereomer mixtures. Both, the pure enantiomers or diastereomers and their mixtures are subject matter of the present invention.

Compounds I can be present in different crystal modifications whose biological activity may differ. They also form part of the subject matter of the present invention. The compounds of formula I can be present in atropisomers arising from restricted rotation about a single bond of asymmetric groups. They also form part of the subject matter of the present invention. The compounds of formula I can be present in atropisomers arising from restricted rotation about a single bond of asymmetric groups. They also form part of the subject matter of the present invention. In respect of the variables, the embodiments of the intermediates correspond to the

embodiments of the compounds of formula I. The term "compounds I" refers to compounds of formula I. Likewise, the term "compounds lla" refers to compounds of formula lla.

In the definitions of the variables given above, collective terms are used which are generally representative for the substituents in question. The term "Cn-Cm" indicates the number of carbon atoms possible in each case in the substituent or substituent moiety in question.

The term "halogen" refers to fluorine, chlorine, bromine and iodine. The term "Ci-C4-alkyl" refers to a straight-chained or branched saturated hydrocarbon group having 1 to 4 carbon atoms, for example methyl, ethyl, propyl, 1 -methylethyl, butyl, 1 - methylpropyl, 2-methylpropyl, and 1 ,1 -dimethylethyl. Likewise, the term "Ci-C6-alkyl" refers to a straight-chained or branched saturated hydrocarbon group having 1 to 6 carbon atoms. The term "Ci-C4-haloalkyl" refers to a straight-chained or branched alkyl group having 1 to 4 carbon atoms (as defined above), wherein some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above, for example chloromethyl,

bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1 -chloroethyl, 1 -bromoethyl, 1 - fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro- 2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl, 2- fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3- chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3- trichloropropyl, CH2-C2F5, CF2-C2F5, CF(CF3)2, 1 -(fluoromethyl)-2-fluoroethyl, l -(chloromethyl)- 2-chloroethyl, 1 -(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl or nonafluorobutyl. Likewise, the term "Ci-C6-haloalkyl" refers to a straight-chained or branched alkyl group having 1 to 6 carbon atoms.

The term "Ci-C4-alkoxy" refers to a straight-chain or branched alkyl group having 1 to 4 carbon atoms (as defined above) which is bonded via an oxygen, at any position in the alkyl group, for example methoxy, ethoxy, n-propoxy, 1 -methylethoxy, butoxy, 1 -methyhpropoxy, 2- methylpropoxy or 1 ,1 -dimethylethoxy. Likewise, the term "Ci-C6-alkoxy" refers to a straight- chain or branched alkyl group having 1 to 6 carbon atoms. The term "Ci-C4-hydroxyalkyl" refers to a straight-chained or branched alkyl group having 2 to 4 carbon atoms (as defined above), wherein one hydrogen atom in these groups may be replaced by one hydroxy group, for example hydroxymethyl,

2-hydroxyethyl, 3-hydroxy-propyl, 4-hydroxy-butyl.

The term "Ci-C4-haloalkoxy" refers to a Ci-C4-alkoxy group as defined above, wherein some or all of the hydrogen atoms may be replaced by halogen atoms as mentioned above, for example, OCH2F, OCH F2, OCF3, OCH2CI, OCHC , OCCIs, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2- difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2- dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, OC2F5, 2-fluoropropoxy, 3-fluoropropoxy, 2,2- difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH2-C2F5, OCF2-C2F5, 1 -(CH2F)-2-fluoroethoxy, 1 -(CH2CI)-2-chloroethoxy, 1 -(CH2Br)-2-bromo-"ethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy. Likewise, the term "C1-C6- haloalkoxy" refers to a Ci-C6-alkoxy group as defined above, wherein some or all of the hydrogen atoms may be replaced by halogen atoms as mentioned above.

The term "Ci-C4-alkoxy-Ci-C4-alkyl" refers to alkyl having 1 to 4 carbon atoms (as defined above), wherein one hydrogen atom of the alkyl radical is replaced by a Ci-C4-alkoxy group (as defined above). Likewise, the term "Ci-C6-alkoxy-Ci-C4-alkyl" refers to alkyl having 1 to 4 carbon atoms (as defined above), wherein one hydrogen atom of the alkyl radical is replaced by a Ci-C6-alkoxy group (as defined above). The term "Ci-C4-haloalkoxy-Ci-C4-alkyl" refers to alkyl having 1 to 4 carbon atoms (as defined above), wherein one hydrogen atom of the alkyl radical is replaced by a Ci-C4-haloalkoxy group (as defined above). Likewise, the term "Ci-C6-haloalkoxy-Ci-C4-alkyl" refers to alkyl having 1 to 4 carbon atoms (as defined above), wherein one hydrogen atom of the alkyl radical is replaced by a Ci-C6-alkoxy group (as defined above).

The term "Ci-C4-alkylthio" as used herein refers to straight-chain or branched alkyl groups having 1 to 4 carbon atoms (as defined above) bonded via a sulfur atom, at any position in the alkyl group, for example methylthio, ethylthio, propylthio, isopropylthio, and n butylthio.

Likewise, the term "Ci-C6-alkylthio" as used herein refers to straight-chain or branched alkyl groups having 1 to 6 carbon atoms (as defined above) bonded via a sulfur atom. Accordingly, the terms "Ci-C4-haloalkylthio" and "Ci-C6-haloalkylthio" as used herein refer to straight-chain or branched haloalkyl groups having 1 to 4 or 1 to 6 carbon atoms (as defined above) bonded through a sulfur atom, at any position in the haloalkyl group. The terms "Ci-C4-alkylsulfinyl" or "Ci-C6-alkylsulfinyl" refer to straight-chain or branched alkyl groups having 1 to 4 or 1 to 6 carbon atoms (as defined above) bonded through a -S(=0)- moiety, at any position in the alkyl group, for example m ethyl su If inyl and ethylsulfinyl, and the like. Accordingly, the terms "Ci-C4-haloalkylsulfinyl" and "Ci-C6-haloalkylsulfinyl", respectively, refer to straight-chain or branched haloalkyi groups having 1 to 4 and 1 to 6 carbon atoms (as defined above), respectively, bonded through a -S(=0)- moiety, at any position in the haloalkyi group.

The terms "Ci-C4-alkylsulfonyl" and "Ci-C6-alkylsulfonyl", respectively, refer to straight-chain or branched alkyl groups having 1 to 4 and 1 to 6 carbon atoms (as defined above), respectively, bonded through a -S(=0)2- moiety, at any position in the alkyl group, for example

methylsulfonyl. Accordingly, the terms "Ci-C4-haloalkylsulfonyl" and "Ci-C6-haloalkylsulfonyl", respectively, refer to straight-chain or branched haloalkyi groups having 1 to 4 and 1 to 6 carbon atoms (as defined above), respectively, bonded through a -S(=0)2- moiety, at any position in the haloalkyi group.

The term "Ci-C4-alkylamino" refers to an amino radical carrying one Ci-C4-alkyl group (as defined above) as substituent, for example methylamino, ethylamino, propylamino, 1 - methylethylamino, butylamino, 1 -methylpropylamino, 2-methylpropylamino, 1 ,1 -di- methylethylamino and the like. Likewise, the term "Ci-C6-alkylamino" refers to an amino radical carrying one Ci-C6-alkyl group (as defined above) as substituent.

The term "di(Ci-C4-alkyl)amino" refers to an amino radical carrying two identical or different Ci- C4-alkyl groups (as defined above) as substituents, for example dimethylamino, diethylamino, di-n-propylamino, diisopropylamino, N-ethyl-N-methylamino, N-(n-propyl)-N-methylamino, N- (isopropyl)-N methylamino, N-(n-butyl)-N-methylamino, N-(n-pentyl)-N-methylamino, N-(2-butyl)- N methylamino, N-(isobutyl)-N-methylamino, and the like. Likewise, the term "di(Ci-C6- alkyl)amino" refers to an amino radical carrying two identical or different Ci-C6-alkyl groups (as defined above) as substituents.

The term "(Ci-C4-alkoxy)carbonyl" refers to a Ci-C4-alkoxy radical (as defined above) which is attached via a carbonyl group.

The term "di(Ci-C4-alkyl)aminocarbonyl" refers to a di(Ci-C4)alkylamino radical as defined above which is attached via a carbonyl group.

The term "phenoxy" and refers to a phenyl radical which is attached via an oxygen atom.

Likewise, the term "phenoxy-Ci-C4-alkyl" and refers to a phenoxy radical which is attached via a Ci-C4-alkyl group (as defined above).

The term "C2-C4-alkenyl" refers to a straight-chain or branched unsaturated hydrocarbon radical having 2 to 4 carbon atoms and a double bond in any position, such as ethenyl, 1 -propenyl, 2- propenyl (allyl), 1 -methylethenyl, 1 -butenyl, 2-butenyl, 3-butenyl, 1 -methyl-1 -propenyl, 2-methyl-

1 - propenyl, 1 -methyl-2-propenyl, 2-methyl-2-propenyl. Likewise, the term "C2-C6-alkenyl" refers to a straight-chain or branched unsaturated hydrocarbon radical having 2 to 6 carbon atoms and a double bond in any position. The term "C2-C4-alkynyl" refers to a straight-chain or branched unsaturated hydrocarbon radical having 2 to 4 carbon atoms and containing at least one triple bond, such as ethynyl, 1 -propynyl,

2- propynyl, 1 -butynyl, 2-butynyl, 3-butynyl, 1 -methyl-2-propynyl. Likewise, the term "C2-C6- alkynyl" refers to a straight-chain or branched unsaturated hydrocarbon radical having 2 to 6 carbon atoms and at least one triple bond.

The term "Cs-Cs-cycloalkyl" refers to monocyclic saturated hydrocarbon radicals having 3 to 8 carbon ring members, such as cyclopropyl (C3H5), cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl. The term "C3-C8-cycloalkyl-Ci-C4-alkyl" refers to a cycloalkyl radical having 3 to 8 carbon atoms (as defined above), which is bonded via a Ci-C4-alkyl group (as defined above).

The term "Cs-Cs-cycloalkyloxy" refers to a cycloalkyl radical having 3 to 8 carbon atoms (as defined above), which is bonded via an oxygen.

The term "saturated or partially unsaturated 3-, 4- 5-, 6- or 7-membered carbocycle" is to be understood as meaning both saturated or partially unsaturated carbocycles having 3, 4, 5, 6 or 7 ring members. Examples include cyclopropyl, cyclopentyl, cyclopentenyl, cyclopentadienyl, cyclohexyl, cyclohexenyl, cyclohexadienyl, cycloheptyl, cycloheptenyl, cycloheptadienyl, and the like.

The term " saturated or partially unsaturated 3-, 4-, 5-, 6-, or 7-membered heterocycle, wherein the ring member atoms of the heterocycle include besides carbon atoms 1 , 2, 3 or 4

heteroatoms selected from the group of N, O and S", is to be understood as meaning both saturated and partially unsaturated heterocycles, for example: a 3- or 4-membered saturated heterocycle which contains 1 or 2 heteroatoms from the group consisting of N, O and S as ring members such as oxirane, aziridine, thiirane, oxetane, azetidine, thiethane, [1 ,2]dioxetane, [1 ,2]dithietane,

[1 ,2]diazetidine; and a 5- or 6-membered saturated or partially unsaturated heterocycle which contains 1 , 2 or 3 heteroatoms from the group consisting of N, O and S as ring members such as 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3- isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4- thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1 ,2,4-oxadiazolidin-3- yl, 1 ,2,4-oxadiazolidin-5-yl, 1 ,2,4-thiadiazolidin-3-yl, 1 ,2,4-thiadiazolidin-5-yl, 1 ,2,4-triazolidin-3-yl, 1 ,3,4-oxadiazolidin-2-yl, 1 ,3,4-thiadiazolidin-2-yl,

1 ,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4- dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2- isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl, 2-isoxazolin-4-yl, 3-isoxazolin-4- yl, 4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yl, 2- isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3- isothiazolin-4-yl, 4-isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4- isothiazolin-5-yl, 2,3-dihydropyrazol-1 -yl, 2,3-dihydropyrazol-2-yl, 2,3- dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4- dihydropyrazol-1 -yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4- dihydropyrazol-5-yl, 4,5-dihydropyrazol-1 -yl, 4,5-dihydropyrazol-3-yl, 4,5- dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3- dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 3,4- dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydro- oxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 1 ,3-dioxan-5-yl, 2-tetrahydropyranyl, 4- tetrahydropyranyl, 2-tetrahydrothienyl, 3-hexahydropyridazinyl, 4-hexa- hydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5-hexahydro- pyrimidinyl, 2-piperazinyl, 1 ,3,5-hexahydrotriazin-2-yl and 1 ,2,4-hexahydrotriazin-3- yl and also the corresponding -ylidene radicals; and a 7-membered saturated or partially unsaturated heterocycle such as tetra- and hexahydroazepinyl, such as 2,3,4,5-tetrahydro[1 H]azepin-1 -,-2-,-3-,-4-,-5-,-6- or-7-yl, 3,4,5,6-tetrahydro[2H]azepin-2-,-3-,-4-,-5-,-6- or-7-yl, 2,3,4,7-tetrahydro[1 H]azepin-1 -,-2-,- 3-,-4-,-5-,-6- or-7-yl, 2,3,6,7-tetrahydro[1 H]azepin-1 -,-2-,-3-,-4-,-5-,-6- or-7-yl,

hexahydroazepin-1 -,-2-,-3- or-4-yl, tetra- and hexahydrooxepinyl such as 2,3,4,5- tetrahydro[1 H]oxepin-2-,-3-,-4-,-5-,-6- or-7-yl, 2,3,4,7-tetrahydro[1 H]oxepin-2-,-3-,-4-,-5-,- 6- or-7-yl, 2,3,6,7-tetrahydro[1 H]oxepin-2-, -3-,-4-,-5-,-6- or-7-yl, hexahydroazepin-1 -,-2-,- 3- or-4-yl, tetra- and hexahydro-1 ,3-diazepinyl, tetra- and hexahydro-1 ,4-diazepinyl, tetra- and hexahydro-1 ,3-oxazepinyl, tetra- and hexahydro-1 ,4-oxazepinyl, tetra- and

hexahydro-1 ,3-dioxepinyl, tetra- and hexahydro-1 ,4-dioxepinyl and the corresponding - ylidene radicals; and

The term "5-or 6-membered heteroaryl, wherein the ring member atoms of the heteroaryl include besides carbon atoms 1 , 2, 3 or 4 heteroatoms selected from the group of N, O and S", refers to, for example, a 5-membered heteroaryl such as pyrrol-1 -yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1 -yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1 -yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3- yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1 ,2,4-triazolyl-1 -yl, 1 ,2,4-triazol-3-yl 1 ,2,4-triazol-5-yl, 1 ,2,4- oxadiazol-3-yl, 1 ,2,4-oxadiazol-5-yl and 1 ,2,4-thiadiazol-3-yl, 1 ,2,4-thiadiazol-5-yl; or a 6-membered heteroaryl, such as pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl and 1 ,3,5-triazin-2- yl and 1 ,2,4-triazin-3-yl.

The term "two radicals Rc that are bound to adjacent ring member atoms form together with said ring member atoms a fused cycle" refers to a condensed bicyclic ring system, wherein 5- or 6- membered heteroaryl carries a fused-on 5-, 6- or 7-membered carbocyclic or heterocyclic ring it being possible that these rings are saturated or partially saturated or aromatic.

The term "one or two Chb groups of the abovementioned cycles may be respectively replaced by one or two C(=0) or C(=S) groups" refers to an exchange of carbon atoms from a saturated or partially unsaturated 3-, 4-, 5-, 6- or 7-membered carbocycle or a saturated or partially unsaturated 3-, 4-, 5-, 6- or 7-membered heterocycle, resulting in cycles such as

cyclopropanone, cyclopentanone, cyclopropanethione, cyclopentanethione, 5-oxazolone, cyclohexane-1 ,4-dione, cyclohexane-1 ,4-dithione, cyclohex-2-ene-1 ,4-dione or cyclohex-2-ene- 1 ,4-dithione.

As regards the fungicidal activity of the compounds I, preference is given to those compounds I wherein the substituents and variables (e.g. Ra2, Ra5, Ra6, R, X, R1, R2, Rb, Rc, Y, R', R", R'", RA, RB, n and Het) have independently of each other or more preferably in combination the following meanings and the groups mentioned herein for a substituent or for a combination of substituents are furthermore, independently of the combination in which they are mentioned, a particularly preferred embodiment of the substituent or of the combination of substituents in question:

One embodiment of the invention relates to compounds I wherein Ra2, Ra5 and Ra6

independently of each other are preferably selected from the group consisting of hydrogen, halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci- C4-haloalkylthio, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy, C2-C4-alkenyl, C2-C4- alkynyl, Cs-Cs-cycloalkyl, Cs-Cs-cycloalkyloxy, (Ci-C4-alkoxy)carbonyl.

A further embodiment relates to compounds I wherein Ra2, Ra5 and Ra6 independently of each other are preferably selected from the group consisting of hydrogen, halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4- alkoxy and (Ci-C4-alkoxy)carbonyl.

A further embodiment relates to compounds I wherein Ra2, Ra5 and Ra6 independently of each other are halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C1-C4- alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy and (Ci-C4-alkoxy)carbonyl, and it being possible that one or two of Ra2, Ra5 or Ra6 can in addition be hydrogen.

Further preferred embodiments relate to compounds I wherein Ra2, Ra5 and Ra6 independently of each other are preferably selected from the group consisting of hydrogen, CI, F, CH3, CH2CH3, OCH3, OCF3, CH2OCH3, CN, OCH2OCH3, CF3,CHFCH3, COOCH3 and COOCH2CH3.

Further preferred embodiments relate to compounds I wherein Ra2, Ra5 and Ra6 independently of each other are preferably selected from the group consisting of CI, F, CH3, CH2CH3, OCH3, OCF3, CH2OCH3, CN, OCH2OCH3, CF3,CHFCH3, COOCH3 and COOCH2CH3.

Further preferred embodiments relate to compounds I wherein Ra2, Ra5 and Ra6 independently of each other are hydrogen, CI, CH3, OCH3, CN or COOCH3.

Further preferred embodiments relate to compounds I wherein Ra2, Ra5 and Ra6 independently of each other are CI, CH3, OCH3, CN or COOCH3. In one preferred embodiment Ra2 is hydrogen, Ci-C6-alkyl or Ci-C6-alkoxy.

Ra2 is CI.

Ra2 is F.

Ra2 is CH3.

Ra2 is CF3.

Figure imgf000020_0001

In one preferred embodiment Ra5 is Ci-C6-alkyl, in particular CH3.

Ra5 is CI.

Ra5 is F.

Ra5 is CF3. A particularly preferred embodiment relates to compounds I wherein Ra5 is OCH3. A particularly preferred embodiment relates to compounds I wherein Ra5 is CO2CH3.

A particularly preferred embodiment relates to compounds I wherein Ra5 is CO2CH2CH3.

In one preferred embodiment Ra6 is hydrogen, halogen, CN, Ci-Ce-alkoxy-Ci-Ce-alkyI or (Ci alkoxy)carbonyl.

A particularly preferred embodiment relates to compounds I wherein Ra6 s CI.

A particularly preferred embodiment relates to compounds I wherein Ra6 s F.

A particularly preferred embodiment relates to compounds I wherein Ra6 s CHs.

A particularly preferred embodiment relates to compounds I wherein Ra6 s CFs.

A particularly preferred embodiment relates to compounds I wherein Ra6 s OCH3.

A particularly preferred embodiment relates to compounds I wherein Ra6 s CO2CH3.

A particularly preferred embodiment relates to compounds I wherein Ra6 S CO2CH2CH3.

Further preferred embodiments relate to compounds I wherein Ra2 and Ra5 in each case are one of the following combinations in Iine1 to line 196 in table A

Figure imgf000021_0001
Figure imgf000022_0001
Figure imgf000023_0001

In the compounds I according to the invention, RA, RB in radical Ra2 preferably is hydrogen, C C4-alkyl.

In the compounds I according to the invention, RA, RB in radical Ra5 preferably is hydrogen, C C4-alkyl. In the compounds I according to the invention, RA, RB in radical Ra6 preferably is hydrogen, Ci- C4-alkyl.

In the compounds I according to the invention, R' in radical Ra2 preferably is hydrogen, Nhb, Ci-C4-alkyl, Ci-C4-alkoxy.

In the compounds I according to the invention, R' in radical Ra5 preferably is hydrogen, Nhb, Ci-C4-alkyl, Ci-C4-alkoxy.

In the compounds I according to the invention, R' in radical Ra6 preferably is hydrogen, Nhb, Ci-C4-alkyl, Ci-C4-alkoxy.

In the compounds I according to the invention, R" in radical Ra2 preferably is hydrogen,

Ci-C4-alkyl.

In the compounds I according to the invention, R" in radical Ra5 preferably is hydrogen,

Ci-C4-alkyl.

In the compounds I according to the invention, R" in radical Ra6 preferably is hydrogen,

Ci-C4-alkyl.

In the compounds I according to the invention, R'" in radical Ra2 preferably is hydrogen.

In the compounds I according to the invention, R'" in radical Ra5 preferably is hydrogen.

In the compounds I according to the invention, R'" in radical Ra6 preferably is hydrogen.

In the compounds I according to the invention, R is preferably selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, C2-C4-alkenyl, C2- C4-alkynyl, CN, CH2CN or CH2-0-C(=0)R', wherein R' is hydrogen, Ci-C4-alkyl, Ci-C4-alkoxy; more preferably R is selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C4-alkoxy- Ci-C4-alkyl, C2-C4-alkenyl and C2-C4-alkynyl; most preferably R is hydrogen or Ci-C4-alkyl; more preferably R is hydrogen; a more preferred embodiment relates to compounds I wherein R is

In the compounds I according to the invention, X is preferably -CH2-,

-CH(CHs), -CH(CH2CH3)-, -C(CH3)2-, -CHCN-, -C(=0)-, -C(=S)-,

-CH(C(=0)-Ci-C4-alkoxy), -CH(C(=0)NH2)-, -C(=0)N(Ci-C4-alkyl)2-, and -CH(C(=0)OH)-; more preferably X is -CH2-,-CH(CH3), -CH(CH2CH3)- or -C(CH3)2-; more preferably X is -CH2-; more preferably X is -C(=0)-.

In the compounds I according to the invention, R1 and R2 independently of each other are preferably selected from the group consisting of hydrogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci- C4-alkoxy, Ci-C4-haloalkoxy and C3-C8-cycloalkyl; more preferably R1 and R2 independently of each other are hydrogen, CN, CH3, CH2CH3, F, CI or OCH3; another more preferred embodiment relates to compounds I wherein R1 and R2 independently of each other are hydrogen or

Ci-C6-alkyl, in particular hydrogen or CH3; more preferably R1 and R2 are hydrogen. In the compounds I according to the invention Y is preferably oxygen. Another preferred embodiment of the invention relates to compounds wherein Y is a direct bond between Het and the phenyl ring. Further preferred embodiments relate to compounds I wherein R, X, R1, R2 and Y in each case are one of the following combinations B-1 to B-144 in table B:

Figure imgf000025_0001
Figure imgf000026_0001
Figure imgf000027_0001
Figure imgf000028_0001

In the compounds I according to the invention, Rb is preferably selected from halogen, CN, N02, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkoxy-Ci-C4-alkyl and (Ci- C4-alkoxy)carbonyl; preferably Rb is selected from halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and (Ci-C4-alkoxy)carbonyl; in another preferred embodiment Rb is selected form halogen, Ci-C6-alkyl and Ci-C6-alkoxy; most preferably Rb is halogen, CN, CH3, CF3, OCH3. A further embodiment relates to compounds I wherein Rb is attached to the phenyl ring adjacent (in ortho-position) to the group -X-CR1R2-0-. A further embodiment relates to compounds I wherein Rb is attached in meta-position to the group -X-CR1R2-0-.

A particularly preferred embodiment relates to compounds I wherein Rb is F.

A particularly preferred embodiment relates to compounds I wherein Rb is CH3.

A particularly preferred embodiment relates to compounds I wherein Rb is CF3.

A particularly preferred embodiment relates to compounds I wherein Rb is OCH3.

In the compounds I according to the invention, n is preferably 0.

A further embodiment relates to compounds I wherein n is preferably 1.

A further embodiment relates to compounds I wherein n is preferably 0 or 1 .

A further embodiment relates to compounds I wherein n is preferably 2.

A further embodiment relates to compounds I wherein n is preferably 0, 1 or 2.

A further embodiment relates to compounds I wherein n is preferably 3.

A further embodiment relates to compounds I wherein n is preferably 0, 1 , 2 or 3.

A further embodiment relates to compounds I wherein n is preferably 4.

In the compounds I according to the invention, Het is preferably selected from the group consisting of pyrimidin-2-yl, pyrimidin-3-yl, pyrimidin-4-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, pyrazin-2-yl, pyridazin-3-yl, 1 ,3,5-triazin-2-yl, and 1 ,2,4-triazin-3-yl; more preferably Het is selected from pyrimidin-2-yl, pyrimidin-3-yl, pyrimidin-4-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, thiazol-2-yl, pyrazin-2-yl, pyridazin-3-yl, 1 ,3,5-triazin-2-yl, and 1 ,2,4-triazin-3-yl; preferably Het is pyrimidin-2- yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, thiazol-2-yl.

In another preferred embodiment Het is a pyridinyl or pyrimidinyl wherein the pyridinyl or pyrimidinyl are unsubstituted or carry 1 or 2 independently selected groups Rc, wherein Rc is halogen, Ci-C6-alkyl or Ci-C6-haloalkyl.

In one embodiment of the invention Het is unsubstituted; a further preferred embodiment relates to compounds I wherein Het is substituted by 1 radical Rc; another preferred embodiment relates to compounds I wherein Het is substituted by 2 radicals Rc; yet another preferred embodiment relates to compounds I wherein Het is substituted by 3 radicals Rc; another preferred embodiment relates to compounds I wherein Het is substituted by 4 radicals Rc.

In the compounds I according to the invention, Rc is preferably selected from the group consisting of halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C(=0)R', C(=NOR")R"', C3-C8-cycloalkyl, phenyl and phenoxy. Another embodiment relates to compounds I wherein Rc is halogen, CN, Ci-C6-alkyl,

Ci-C6-haloalkyl, Ci-C6-alkoxy or Ci-C6-haloalkoxy. In still another embodiment Rc is halogen, Ci-C6-alkyl or Ci-C6-haloalkyl. A further embodiment relates to compounds I wherein Rc is F, CI, CN, CH3, OCH3, CF3, OCF3 or COOCH3; most preferably Rc is CI, CN, CF3.

Preferred embodiments of the invention relate to compounds I, in which the group Het is one of the following radicals H-1 to H-38 in table H, wherein # indicates the point of attachment:

Figure imgf000030_0001
Figure imgf000031_0001

With res ect to their use, particular preference is given to the compounds I. A or I. B.

Figure imgf000031_0002

A skilled person will readily understand that the preferences given in connection with compounds of formula I also apply for formulae I .A or I.B as defined herein.

According to a further embodiment, the present invention relates to compounds of the formula I wherein:

Ra2, Ra5, Ra6 independently of each other are hydrogen, halogen, CN, Ci-C6-alkyl,

Ci-C6-alkoxy, Ci-C6-alkoxy-Ci-C6-alkyl or (Ci-C4-alkoxy)carbonyl;

R is hydrogen or Ci-C4-alkyl;

X is -CH2-,-CH(CH3), -CH(CH2CH3)- or -C(CH3)2-;

R1, R2 are independently selected from hydrogen or Ci-C6-alkyl;

n is O or l ;

Rb is halogen, Ci-C6-alkyl or Ci-C6-alkoxy;

Het is a pyridinyl or pyrimidinyl wherein the pyridinyl or pyrimidinyl are unsubstituted or carry 1 or 2 independently selected groups Rc; wherein

Rc is halogen, Ci-C6-alkyl or Ci-C6-haloalkyl; and

the N-oxides and the agriculturally acceptable salts of the compounds of formula I.

The compounds I and the compositions according to the invention, respectively, are suitable as fungicides. They are distinguished by an outstanding effectiveness against a broad spectrum of phytopathogenic fungi, including soil-borne fungi, which derive especially from the classes of the Plasmodiophoromycetes, Peronosporomycetes (syn. Oomycetes), Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes (syn. Fungi imperfecti). Some are systemically effective and they can be used in crop protection as foliar fungicides, fungicides for seed dressing and soil fungicides. Moreover, they are suitable for controlling harmful fungi, which inter alia occur in wood or roots of plants.

The compounds I and the compositions according to the invention are particularly important in the control of a multitude of phytopathogenic fungi on various cultivated plants, such as cereals, e. g. wheat, rye, barley, triticale, oats or rice; beet, e. g. sugar beet or fodder beet; fruits, such as pomes, stone fruits or soft fruits, e. g. apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, blackberries or gooseberries; leguminous plants, such as lentils, peas, alfalfa or soybeans; oil plants, such as rape, mustard, olives, sunflowers, coconut, cocoa beans, castor oil plants, oil palms, ground nuts or soybeans; cucurbits, such as squashes, cucumber or melons; fiber plants, such as cotton, flax, hemp or jute; citrus fruit, such as oranges, lemons, grapefruits or mandarins; vegetables, such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, cucurbits or paprika; lauraceous plants, such as avocados, cinnamon or camphor; energy and raw material plants, such as corn, soybean, rape, sugar cane or oil palm; corn; tobacco; nuts; coffee; tea; bananas; vines (table grapes and grape juice grape vines); hop; turf; sweet leaf (also called Stevia); natural rubber plants or ornamental and forestry plants, such as flowers, shrubs, broad-leaved trees or evergreens, e. g. conifers; and on the plant propagation material, such as seeds, and the crop material of these plants. Preferably, compounds I and compositions thereof, respectively are used for controlling a multitude of fungi on field crops, such as potatoes sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rape, legumes, sunflowers, coffee or sugar cane; fruits; vines; ornamentals; or vegetables, such as cucumbers, tomatoes, beans or squashes.

The term "plant propagation material" is to be understood to denote all the generative parts of the plant such as seeds and vegetative plant material such as cuttings and tubers (e. g.

potatoes), which can be used for the multiplication of the plant. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants, including seedlings and young plants, which are to be transplanted after germination or after emergence from soil.

These young plants may also be protected before transplantation by a total or partial treatment by immersion or pouring.

Preferably, treatment of plant propagation materials with compounds I and compositions thereof, respectively, is used for controlling a multitude of fungi on cereals, such as wheat, rye, barley and oats; rice, corn, cotton and soybeans.

The term "cultivated plants" is to be understood as including plants which have been modified by breeding, mutagenesis or genetic engineering including but not limiting to agricultural biotech products on the market or in development (cf. http://cera-gmc.org/, see GM crop database therein). Genetically modified plants are plants, which genetic material has been so modified by the use of recombinant DNA techniques that under natural circumstances cannot readily be obtained by cross breeding, mutations or natural recombination. Typically, one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant. Such genetic modifications also include but are not limited to targeted post-translational modification of protein(s), oligo- or polypeptides e. g. by glycosylation or polymer additions such as prenylated, acetylated or farnesylated moieties or PEG moieties. Plants that have been modified by breeding, mutagenesis or genetic engineering, e. g. have been rendered tolerant to applications of specific classes of herbicides, such as auxin herbicides such as dicamba or 2,4-D; bleacher herbicides such as hydroxylphenylpyruvate dioxygenase (HPPD) inhibitors or phytoene desaturase (PDS) inhibittors; acetolactate synthase (ALS) inhibitors such as sulfonyl ureas or imidazolinones; enolpyruvylshikimate-3-phosphate synthase (EPSPS) inhibitors, such as glyphosate; glutamine synthetase (GS) inhibitors such as glufosinate; protoporphyrinogen-IX oxidase inhibitors; lipid biosynthesis inhibitors such as acetyl CoA carboxylase (ACCase) inhibitors; or oxynil (i. e. bromoxynil or ioxynil) herbicides as a result of conventional methods of breeding or genetic engineering. Furthermore, plants have been made resistant to multiple classes of herbicides through multiple genetic modifications, such as resistance to both glyphosate and glufosinate or to both glyphosate and a herbicide from another class such as ALS inhibitors, HPPD inhibitors, auxin herbicides, or ACCase inhibitors. These herbicide resistance technologies are e. g. described in Pest Managem. Sci. 61 , 2005, 246; 61 , 2005, 258; 61 , 2005, 277; 61 , 2005, 269; 61 , 2005, 286; 64, 2008, 326; 64, 2008, 332; Weed Sci. 57, 2009, 108; Austral. J. Agricult. Res. 58, 2007, 708; Science 316, 2007, 1 185; and references quoted therein. Several cultivated plants have been rendered tolerant to herbicides by conventional methods of breeding (mutagenesis), e. g. Clearfield® summer rape (Canola, BASF SE, Germany) being tolerant to imidazolinones, e. g. imazamox, or ExpressSun® sunflowers (DuPont, USA) being tolerant to sulfonyl ureas, e. g. tribenuron. Genetic engineering methods have been used to render cultivated plants such as soybean, cotton, corn, beets and rape, tolerant to herbicides such as glyphosate and glufosinate, some of which are

commercially available under the trade names RoundupReady® (glyphosate-tolerant, Monsanto, U.S.A.), Cultivance® (imidazolinone tolerant, BASF SE, Germany) and LibertyLink® (glufosinate- tolerant, Bayer CropScience, Germany).

Furthermore, plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more insecticidal proteins, especially those known from the bacterial genus Bacillus, particularly from Bacillus thuringiensis, such as δ-endotoxins, e. g. CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA, CrylllB(bl ) or Cry9c; vegetative insecticidal proteins (VIP), e. g. VIP1 , VIP2, VIP3 or VIP3A; insecticidal proteins of bacteria colonizing nematodes, e. g. Photorhabdus spp. or Xenorhabdus spp.; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins; toxins produced by fungi, such Streptomycetes toxins, plant lectins, such as pea or barley lectins; agglutinins; proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such as 3- hydroxysteroid oxidase, ecdysteroid-IDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase; ion channel blockers, such as blockers of sodium or calcium channels; juvenile hormone esterase; diuretic hormone receptors (helicokinin receptors); stilben synthase, bibenzyl synthase, chitinases or glucanases. In the context of the present invention these insecticidal proteins or toxins are to be understood expressly also as pre-toxins, hybrid proteins, truncated or otherwise modified proteins. Hybrid proteins are characterized by a new combination of protein domains, (see, e. g. WO 02/015701 ). Further examples of such toxins or genetically modified plants capable of synthesizing such toxins are disclosed, e. g., in

EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO 03/18810 und WO 03/52073. The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e. g. in the publications mentioned above. These insecticidal proteins contained in the genetically modified plants impart to the plants producing these proteins tolerance to harmful pests from all taxonomic groups of athropods, especially to beetles (Coeloptera), two-winged insects (Diptera), and moths (Lepidoptera) and to nematodes (Nematoda). Genetically modified plants capable to synthesize one or more insecticidal proteins are, e. g., described in the publications mentioned above, and some of which are commercially available such as YieldGard® (corn cultivars producing the Cry1 Ab toxin), YieldGard® Plus (corn cultivars producing CrylAb and Cry3Bb1 toxins), Starlink® (corn cultivars producing the Cry9c toxin), Herculex® RW (corn cultivars producing Cry34Ab1 , Cry35Ab1 and the enzyme Phosphinothricin-N-Acetyltransferase [PAT]); NuCOTN® 33B (cotton cultivars producing the CrylAc toxin), Bollgard® I (cotton cultivars producing the Cry1 Ac toxin), Bollgard® II (cotton cultivars producing CrylAc and Cry2Ab2 toxins); VIPCOT® (cotton cultivars producing a VIP-toxin); NewLeaf® (potato cultivars producing the Cry3A toxin); Bt-Xtra®, NatureGard®, KnockOut®, BiteGard®, Protecta®, Bt1 1 (e. g. Agrisure® CB) and Bt176 from Syngenta Seeds SAS, France, (corn cultivars producing the CrylAb toxin and PAT enyzme), MIR604 from Syngenta Seeds SAS, France (corn cultivars producing a modified version of the Cry3A toxin, c.f. WO 03/018810), MON 863 from Monsanto Europe S.A., Belgium (corn cultivars producing the Cry3Bb1 toxin), IPC 531 from Monsanto Europe S.A., Belgium (cotton cultivars producing a modified version of the CrylAc toxin) and 1507 from Pioneer Overseas

Corporation, Belgium (corn cultivars producing the Cry1 F toxin and PAT enzyme).

Furthermore, plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the resistance or tolerance of those plants to bacterial, viral or fungal pathogens. Examples of such proteins are the so-called "pathogenesis-related proteins" (PR proteins, see, e. g. EP-A 392 225), plant disease resistance genes (e. g. potato cultivars, which express resistance genes acting against Phytophthora infestans derived from the mexican wild potato Solanum bulbocastanum) or T4-lysozym (e. g. potato cultivars capable of synthesizing these proteins with increased resistance against bacteria such as Erwinia amylvora). The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e. g. in the publications mentioned above.

Furthermore, plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the productivity (e. g. bio mass production, grain yield, starch content, oil content or protein content), tolerance to drought, salinity or other growth-limiting environmental factors or tolerance to pests and fungal, bacterial or viral pathogens of those plants.

Furthermore, plants are also covered that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve human or animal nutrition, e. g. oil crops that produce health-promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (e. g. Nexera® rape, DOW Agro Sciences, Canada).

Furthermore, plants are also covered that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve raw material production, e. g. potatoes that produce increased amounts of amylopectin (e. g. Amflora® potato, BASF SE, Germany).

The compounds I and compositions thereof, respectively, are particularly suitable for controlling the following plant diseases: Albugo spp. (white rust) on ornamentals, vegetables (e. g. A. Candida) and sunflowers (e. g. A. tragopogonis); Altemaria spp. (Alternaria leaf spot) on vegetables, rape (A. brassicola or brassicae), sugar beets (A. tenuis), fruits, rice, soybeans, potatoes (e. g. A. solani or A.

alternata), tomatoes (e. g. A. solani or A. alternata) and wheat; Aphanomyces spp. on sugar beets and vegetables; Ascochyta spp. on cereals and vegetables, e. g. A. tritici (anthracnose) on wheat and A. hordei on barley; Bipolaris and Drechslera spp. (teleomorph: Cochliobolus spp.), e. g. Southern leaf blight (D. maydis) or Northern leaf blight (B. zeicola) on corn, e. g. spot blotch (6. sorokiniana) on cereals and e.g. B. oryzae on rice and turfs; Blumeria (formerly Erysiphe) graminis (powdery mildew) on cereals (e. g. on wheat or barley); Botrytis cinerea (teleomorph: Botryotinia fuckeliana: grey mold) on fruits and berries (e. g. strawberries), vegetables (e. g. lettuce, carrots, celery and cabbages), rape, flowers, vines, forestry plants and wheat; Bremia lactucae (downy mildew) on lettuce; Ceratocystis (syn. Ophiostoma) spp. (rot or wilt) on broad-leaved trees and evergreens, e. g. C. ulmi (Dutch elm disease) on elms;

Cercospora spp. (Cercospora leaf spots) on corn (e.g. Gray leaf spot: C. zeae-maydis), rice, sugar beets (e. g. C. beticola), sugar cane, vegetables, coffee, soybeans (e. g. C. sojina or C. kikuchii) and rice; Cladosporium spp. on tomatoes (e. g. C. fulvum: leaf mold) and cereals, e. g. C. herbarum (black ear) on wheat; Claviceps purpurea (ergot) on cereals; Cochliobolus

(anamorph: Helminthosporium of Bipolaris) spp. (leaf spots) on corn (C. carbonum), cereals (e. g. C. sativus, anamorph: B. sorokiniana) and rice (e. g. C. miyabeanus, anamorph: H.

oryzae); Colletotrichum (teleomorph: Glomerella) spp. (anthracnose) on cotton (e. g. C.

gossypii), corn (e. g. C. graminicola: Anthracnose stalk rot), soft fruits, potatoes (e. g. C.

coccodes: black dot), beans (e. g. C. lindemuthianum) and soybeans (e. g. C. truncatum or C. gloeosporioides); Corticium spp., e. g. C. sasakii (sheath blight) on rice; Corynespora cassiicola (leaf spots) on soybeans and ornamentals; Cycloconium spp., e. g. C. oleaginum on olive trees; Cylindrocarpon spp. (e. g. fruit tree canker or young vine decline, teleomorph: Nectria or Neonectria spp.) on fruit trees, vines (e. g. C. liriodendri, teleomorph: Neonectria liriodendri: Black Foot Disease) and ornamentals; Dematophora (teleomorph: Rosellinia) necatrix (root and stem rot) on soybeans; Diaporthe spp., e. g. D. phaseolorum (damping off) on soybeans;

Drechslera (syn. Helminthosporium, teleomorph: Pyrenophora) spp. on corn, cereals, such as barley (e. g. D. teres, net blotch) and wheat (e. g. D. tritici-repentis: tan spot), rice and turf; Esca (dieback, apoplexy) on vines, caused by Formitiporia (syn. Phellinus) punctata, F. mediterranea, Phaeomoniella chlamydospora (earlier Phaeoacremonium chlamydosporum),

Phaeoacremonium aleophilum and/or Botryosphaeria obtusa; Elsinoe spp. on pome fruits (£. pyri), soft fruits (£. veneta: anthracnose) and vines (£. ampelina: anthracnose); Entyloma oryzae (leaf smut) on rice; Epicoccum spp. (black mold) on wheat; Erysiphe spp. (powdery mildew) on sugar beets (£. betae), vegetables (e. g. E. pisi), such as cucurbits (e. g. E.

cichoracearum), cabbages, rape (e. g. E. cruciferarum); Eutypa lata (Eutypa canker or dieback, anamorph: Cytosporina lata, syn. Libertella blepharis) on fruit trees, vines and ornamental woods; Exserohilum (syn. Helminthosporium) spp. on corn (e. g. E. turcicum); Fusarium

(teleomorph: Gibberella) spp. (wilt, root or stem rot) on various plants, such as F. graminearum or F. culmorum (root rot, scab or head blight) on cereals (e. g. wheat or barley), F. oxysporum on tomatoes, F. solani on soybeans and F. verticillioides on corn; Gaeumannomyces graminis (take-all) 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 vines, pome fruits and other plants and G. gossypii on cotton; Grainstaining complex on rice; Guignardia bidwellii (black rot) on vines; Gymnosporangium spp. on rosaceous plants and junipers, e. g. G. sabinae (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 vines; Macrophomina phaseolina (syn. phaseoli) (root and 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 (bloom and twig blight, brown rot) on stone fruits and other rosaceous plants; Mycosphaerella spp. on cereals, bananas, soft fruits and ground nuts, such as e. g. M. graminicola (anamorph: Septoria tritici, Septoria blotch) on wheat or M. fijiensis (black Sigatoka disease) on bananas; Peronospora spp. (downy mildew) on cabbage (e. g. P. brassicae), rape (e. g. P. parasitica), onions (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 vines (e. g. P. tracheiphila and P.

tetraspora) and soybeans (e. g. P. gregata: stem rot); Phoma lingam (root and stem rot) on rape and cabbage and P. betae (root rot, leaf spot and damping-off) on sugar beets; Phomopsis spp. on sunflowers, vines (e. g. P. viticola: can and leaf spot) and soybeans (e. g. stem rot: P.

phaseoli, teleomorph: Diaporthe phaseolorum); Physoderma maydis (brown spots) on corn; Phytophthora spp. (wilt, root, leaf, fruit and stem root) on various plants, such as paprika and cucurbits (e. g. P. capsici), soybeans (e. g. P. megasperma, syn. P. sojae), potatoes and tomatoes (e. g. P. infestans: late blight) and broad-leaved trees (e. g. P. ramorum: sudden oak death); Plasmodiophora brassicae (club root) on cabbage, rape, radish and other plants;

Plasmopara spp., e. g. P. viticola (grapevine downy mildew) on vines and P. halstedii on sunflowers; Podosphaera spp. (powdery mildew) on rosaceous plants, hop, pome and soft fruits, e. g. P. leucotricha on apples; Polymyxa spp., e. g. on cereals, such as barley and wheat (P. graminis) and sugar beets (P. betae) and thereby transmitted viral diseases;

Pseudocercosporella herpotrichoides (eyespot, teleomorph: Tapesia yallundae) on cereals, e. g. wheat or barley; Pseudoperonospora (downy mildew) on various plants, e. g. P. cubensis on cucurbits or P. humili on hop; Pseudopezicula tracheiphila (red fire disease or .rotbrenner', anamorph: Phialophora) on vines; Puccinia spp. (rusts) on various plants, e. g. P. triticina (brown or leaf rust), P. striiformis (stripe or yellow rust), P. hordei (dwarf rust), P. graminis (stem or black rust) or P. recondita (brown or leaf rust) on cereals, such as e. g. wheat, barley or rye, P. kuehnii (orange rust) on sugar cane and P. asparagi on asparagus; Pyrenophora (anamorph: Drechslera) tritici-repentis (tan spot) on wheat or P. feres (net blotch) on barley; Pyricularia spp., e. g. P. oryzae (teleomorph: Magnaporthe grisea, rice blast) on rice and P. grisea on turf and cereals; Pythium spp. (damping-off) on turf, rice, corn, wheat, cotton, rape, sunflowers, soybeans, sugar beets, vegetables and various other plants (e. g. P. ultimum or P. aphani- dermatum); Ramularia spp., e. g. R. collo-cygni (Ram ularia leaf spots, Physiological leaf spots) on barley and R. beticola on sugar beets; Rhizoctonia spp. on cotton, rice, potatoes, turf, corn, rape, potatoes, sugar beets, vegetables and various other plants, e. g. R. solani (root and stem rot) on soybeans, R. solani (sheath blight) on rice or R. cerealis (Rhizoctonia spring blight) on wheat or barley; Rhizopus stolonifer (black mold, soft rot) on strawberries, carrots, cabbage, vines and tomatoes; Rhynchosporium secalis (scald) on barley, rye and triticale; Sarocladium oryzae and S. attenuatum (sheath rot) on rice; Sclerotinia spp. (stem rot or white mold) on vegetables and field crops, such as rape, sunflowers (e. g. S. sclerotiorum) and soybeans (e. g. S. rolfsii or S. sclerotiorum); Septoria spp. on various plants, e. g. S. glycines (brown spot) on soybeans, S. tritici (Septoria blotch) on wheat and S. (syn. Stagonospora) nodorum

(Stagonospora blotch) on cereals; Uncinula (syn. Erysiphe) necator (powdery mildew, anamorph: Oidium tuckeri) on vines; Setospaeria spp. (leaf blight) on corn (e. g. S. turcicum, syn. Helminthosporium turcicum) and turf; Sphacelotheca spp. (smut) on corn, (e. g. S. reiliana: head smut), sorghum und sugar cane; Sphaerotheca fuliginea (powdery mildew) on cucurbits; Spongospora subterranea (powdery scab) on potatoes and thereby transmitted viral diseases; Stagonospora spp. on cereals, e. g. S. nodorum (Stagonospora blotch, teleomorph:

Leptosphaeria [syn. Phaeosphaeria] nodorum) on wheat; Synchytrium endobioticum on potatoes (potato wart disease); Taphrina spp., e. g. T. deformans (leaf curl disease) on peaches and T. pruni (plum pocket) on plums; Thielaviopsis spp. (black root rot) on tobacco, pome fruits, vegetables, soybeans and cotton, e. g. T. basicola (syn. Chalara elegans); Tilletia spp.

(common 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 (grey snow mold) on barley or wheat; Urocystis spp., e. g. U. occulta (stem smut) on rye; Uromyces spp. (rust) on vegetables, such as beans (e. g. U. appendiculatus, syn. U. phaseoli) and sugar beets (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. (wilt) on various plants, such as fruits and ornamentals, vines, soft fruits, vegetables and field crops, e. g. V. dahliae on strawberries, rape, potatoes and tomatoes.

The compounds I and compositions thereof, respectively, are also suitable for controlling harmful fungi in the protection of stored products or harvest and in the protection of materials. The term "protection of materials" is to be understood to denote the protection of technical and non-living materials, such as adhesives, glues, wood, paper and paperboard, textiles, leather, paint dispersions, plastics, colling lubricants, fiber or fabrics, against the infestation and destruction by harmful microorganisms, such as fungi and bacteria. As to the protection of wood and other materials, the particular attention is paid to the following harmful fungi: Ascomycetes such as Ophiostoma spp., Ceratocystis spp., Aureobasidium pullulans, Sclerophoma spp., Chaetomium spp., Humicola spp., Petriella spp., Trichurus spp.; Basidiomycetes such as Coniophora spp., Coriolus spp., Gloeophyllum spp., Lentinus spp., Pleurotus spp., Poria spp., Serpula spp. and Tyromyces spp., Deuteromycetes such as Aspergillus spp., Cladosporium spp., Penicillium spp., Trichorma spp., Alternaria spp., Paecilomyces spp. and Zygomycetes such as Mucor spp., and in addition in the protection of stored products and harvest the following yeast fungi are worthy of note: Candida spp. and Saccharomyces cerevisae.

The compounds I and compositions thereof, resepectively, may be used for improving the health of a plant. The invention also relates to a method for improving plant health by treating a plant, its propagation material and/or the locus where the plant is growing or is to grow with an effective amount of compounds I and compositions thereof, respectively.

The term "plant health" is to be understood to denote a condition of the plant and/or its products which is determined by several indicators alone or in combination with each other such as yield (e. g. increased biomass and/or increased content of valuable ingredients), plant vigor (e. g. improved plant growth and/or greener leaves ("greening effect")), quality (e. g. improved content or composition of certain ingredients) and tolerance to abiotic and/or biotic stress. The above identified indicators for the health condition of a plant may be interdependent or may result from each other.

The compounds of formula I can be present in different crystal modifications whose biological activity may differ. They are likewise subject matter of the present invention.

The compounds I are employed as such or in form of compositions by treating the fungi or the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms to be protected from fungal attack with a fungicidally effective amount of the active substances. The application can be carried out both before and after the infection of the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms by the fungi.

Plant propagation materials may be treated with compounds I as such or a composition comprising at least one compound I prophylactically either at or before planting or transplanting. The invention also relates to agrochemical compositions comprising an auxiliary and at least one compound I according to the invention.

An agrochemical composition comprises a fungicidally effective amount of a compound I. The term "effective amount" denotes an amount of the composition or of the compounds I, which is sufficient for controlling harmful fungi on cultivated plants or in the protection of materials and which does not result in a substantial damage to the treated plants. Such an amount can vary in a broad range and is dependent on various factors, such as the fungal species to be controlled, the treated cultivated plant or material, the climatic conditions and the specific compound I used.

The compounds I, their N-oxides and salts can be converted into customary types of agrochemical compositions, e. g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof. Examples for composition types are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME), capsules (e.g. CS, ZC), pastes, pastilles, wettable powders or dusts (e.g. WP, SP, WS, DP, DS), pressings (e.g. BR, TB, DT), granules (e.g. WG, SG, GR, FG, GG, MG), insecticidal articles (e.g. LN), as well as gel formulations for the treatment of plant propagation materials such as seeds (e.g. GF). These and further compositions types are defined in the "Catalogue of pesticide formulation types and international coding system", Technical

Monograph No. 2, 6th Ed. May 2008, CropLife International.

The compositions are prepared in a known manner, such as described by Mollet and

Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001 ; or Knowles, New

developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005. Suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants,

compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifiers and binders.

Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil fractions of medium to high boiling point, e.g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e. g. toluene, paraffin,

tetrahydronaphthalene, alkylated naphthalenes; alcohols, e.g. ethanol, propanol, butanol, benzylalcohol, cyclohexanol; glycols; DMSO; ketones, e.g. cyclohexanone; esters, e.g. lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e.g. N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof.

Suitable solid carriers or fillers are mineral earths, e.g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides, e.g. cellulose, starch; fertilizers, e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e.g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.

Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emusifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid, or adjuvant. Examples of surfactants are listed in McCutcheon's, Vol.1 : Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).

Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof. Examples of sulfonates are alkylarylsulfonates, diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkylnaphthalenes, sulfosuccinates or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates.

Suitable nonionic surfactants are alkoxylates, N-subsituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents. Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide.

Examples of N-subsititued fatty acid amides are fatty acid glucamides or fatty acid

alkanolamides. Examples of esters are fatty acid esters, glycerol esters or monoglycerides.

Examples of sugar-based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpolyglucosides. Examples of polymeric surfactants are home- or copolymers of vinylpyrrolidone, vinylalcohols, or vinylacetate.

Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkylbetains and imidazolines. Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamines or polyethyleneamines.

Suitable adjuvants are compounds, which have a neglectable or even no pesticidal activity themselves, and which improve the biological performance of the compound I on the target. Examples are surfactants, mineral or vegetable oils, and other auxilaries. Further examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.

Suitable thickeners are polysaccharides (e.g. xanthan gum, carboxymethylcellulose), anorganic clays (organically modified or unmodified), polycarboxylates, and silicates.

Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones.

Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.

Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids.

Suitable colorants (e.g. in red, blue, or green) are pigments of low water solubility and water- soluble dyes. Examples are inorganic colorants (e.g. iron oxide, titan oxide, iron

hexacyanoferrate) and organic colorants (e.g. alizarin-, azo- and phthalocyanine colorants). Suitable tackifiers or binders are polyvinylpyrrolidone, polyvinylacetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.

Examples for composition types and their preparation are:

i) Water-soluble concentrates (SL, LS)

10-60 wt% of a compound I and 5-15 wt% wetting agent (e.g. alcohol alkoxylates) are dissolved in water and/or in a water-soluble solvent (e.g. alcohols) ad 100 wt%. The active substance dissolves upon dilution with water.

ii) Dispersible concentrates (DC)

5-25 wt% of a compound I and 1 -10 wt% dispersant (e. g. polyvinylpyrrolidone) are dissolved in organic solvent (e.g. cyclohexanone) ad 100 wt%. Dilution with water gives a dispersion.

iii) Emulsifiable concentrates (EC)

15-70 wt% of a compound I and 5-10 wt% emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in water-insoluble organic solvent (e.g. aromatic hydrocarbon) ad 100 wt%. Dilution with water gives an emulsion.

iv) Emulsions (EW, EO, ES)

5-40 wt% of a compound I and 1 -10 wt% emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20-40 wt% water-insoluble organic solvent (e.g. aromatic hydrocarbon). This mixture is introduced into water ad 100 wt% by means of an emulsifying machine and made into a homogeneous emulsion. Dilution with water gives an emulsion.

v) Suspensions (SC, OD, FS)

In an agitated ball mill, 20-60 wt% of a compound I are comminuted with addition of 2-10 wt% dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate), 0.1 -2 wt% thickener (e.g. xanthan gum) and water ad 100 wt% to give a fine active substance suspension. Dilution with water gives a stable suspension of the active substance. For FS type composition up to 40 wt% binder (e.g. polyvinylalcohol) is added.

vi) Water-dispersible granules and water-soluble granules (WG, SG)

50-80 wt% of a compound I are ground finely with addition of dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate) ad 100 wt% and prepared as water- dispersible or water-soluble granules by means of technical appliances (e. g. extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substance.

vii) Water-dispersible powders and water-soluble powders (WP, SP, WS)

50-80 wt% of a compound I are ground in a rotor-stator mill with addition of 1 -5 wt% dispersants (e.g. sodium lignosulfonate), 1 -3 wt% wetting agents (e.g. alcohol ethoxylate) and solid carrier (e.g. silica gel) ad 100 wt%. Dilution with water gives a stable dispersion or solution of the active substance.

viii) Gel (GW, GF)

In an agitated ball mill, 5-25 wt% of a compound I are comminuted with addition of 3-10 wt% dispersants (e.g. sodium lignosulfonate), 1 -5 wt% thickener (e.g. carboxymethylcellulose) and water ad 100 wt% to give a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance.

ix) Microemulsion (ME)

5-20 wt% of a compound I are added to 5-30 wt% organic solvent blend (e.g. fatty acid dimethylamide and cyclohexanone), 10-25 wt% surfactant blend (e.g. alcohol ethoxylate and arylphenol ethoxylate), and water ad 100 %. This mixture is stirred for 1 h to produce

spontaneously a thermodynamically stable microemulsion.

x) Microcapsules (CS)

An oil phase comprising 5-50 wt% of a compound I, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), 2-15 wt% acrylic monomers (e.g. methylmethacrylate, methacrylic acid and a di- or triacrylate) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). Radical polymerization initiated by a radical initiator results in the formation of poly(meth)acrylate microcapsules. Alternatively, an oil phase comprising 5-50 wt% of a compound I according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), and an isocyanate monomer (e.g. diphenylmethene-4,4'-diisocyanatae) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). The addition of a polyamine (e.g. hexamethylenediamine) results in the formation of polyurea microcapsules. The monomers amount to 1 -10 wt%. The wt% relate to the total CS composition.

xi) Dustable powders (DP, DS) 1 -10 wt% of a compound I are ground finely and mixed intimately with solid carrier (e.g. finely divided kaolin) ad 100 wt%.

xii) Granules (GR, FG)

0.5-30 wt% of a compound I is ground finely and associated with solid carrier (e.g. silicate) ad 100 wt%. Granulation is achieved by extrusion, spray-drying or fluidized bed.

xiii) Ultra-low volume liquids (UL)

1 -50 wt% of a compound I are dissolved in organic solvent (e.g. aromatic hydrocarbon) ad 100 wt%.

The compositions types i) to xiii) may optionally comprise further auxiliaries, such as 0.1 -1 wt% bactericides, 5-15 wt% anti-freezing agents, 0.1 -1 wt% anti-foaming agents, and 0.1 -1 wt% colorants.

The agrochemical compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, and in particular between 0.5 and 75%, by weight of active substance. The active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).

Solutions for seed treatment (LS), Suspoemulsions (SE), flowable concentrates (FS), powders for dry treatment (DS), water-dispersible powders for slurry treatment (WS), water-soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC) and gels (GF) are usually employed for the purposes of treatment of plant propagation materials, particularly seeds. The compositions in question give, after two-to-tenfold dilution, active substance concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40%, in the ready-to-use preparations.

Application can be carried out before or during sowing. Methods for applying compound I and compositions thereof, respectively, on to plant propagation material, especially seeds include dressing, coating, pelleting, dusting, soaking and in-furrow application methods of the propagation material. Preferably, compound I or the compositions thereof, respectively, are applied on to the plant propagation material by a method such that germination is not induced, e. g. by seed dressing, pelleting, coating and dusting. When employed in plant protection, the amounts of active substances applied are, depending on the kind of effect desired, from 0.001 to 2 kg per ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.05 to 0.9 kg per ha, and in particular from 0.1 to 0.75 kg per ha.

In treatment of plant propagation materials such as seeds, e. g. by dusting, coating or drenching seed, amounts of active substance of from 0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to 100 g and most preferably from 5 to 100 g, per 100 kilogram of plant propagation material (preferably seeds) are generally required.

When used in the protection of materials or stored products, the amount of active substance applied depends on the kind of application area and on the desired effect. Amounts customarily applied in the protection of materials are 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active substance per cubic meter of treated material.

Various types of oils, wetters, adjuvants, fertilizer, or micronutrients, and further pesticides (e.g. herbicides, insecticides, fungicides, growth regulators, safeners) may be added to the active substances or the compositions comprising them as premix or, if appropriate not until immediately prior to use (tank mix). These agents can be admixed with the compositions according to the invention in a weight ratio of 1 :100 to 100:1 , preferably 1 :10 to 10:1.

The user applies the composition according to the invention usually from a predosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system. Usually, the

agrochemical composition is made up with water, buffer, and/or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained. Usually, 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.

According to one embodiment, individual components of the composition according to the invention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank and further auxiliaries may be added, if appropriate.

Mixing the compounds I or the compositions comprising them in the use form as fungicides with other fungicides results in many cases in an expansion of the fungicidal spectrum of activity being obtained or in a prevention of fungicide resistance development. Furthermore, in many cases, synergistic effects are obtained.

The following list of active substances, in conjunction with which the compounds I can be used, is intended to illustrate the possible combinations but does not limit them:

A) Respiration inhibitors

- Inhibitors of complex III at Q0 site (e.g. strobilurins): azoxystrobin, coumethoxystrobin, coumoxystrobin, dimoxystrobin, enestroburin, fenaminstrobin, fenoxystrobin/flufenoxystrobin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, trifloxystrobin, 2-[2-(2,5-dimethyl-phenoxymethyl)-phenyl]-3- methoxy-acrylic acid methyl ester and 2-(2-(3-(2,6-dichlorophenyl)-1 -methyl-allylideneaminooxy- methyl)-phenyl)-2-methoxyimino-N-methyl-acetamide, pyribencarb, triclopyricarb/chlorodincarb, famoxadone, fenamidone;

inhibitors of complex III at Q, site: cyazofamid, amisulbrom, [(3S,6S,7R,8R)-8-benzyl-3-[(3- acetoxy-4-methoxy-pyridine-2-carbonyl)amino]-6-methyl-4,9-dioxo-1 ,5-dioxonan-7-yl]

2- methylpropanoate, [(3S,6S,7R,8R)-8-benzyl-3-[[3-(acetoxymethoxy)-4-methoxy-pyridine- 2-carbonyl]amino]-6-methyl-4,9-dioxo-1 ,5-dioxonan-7-yl] 2-methylpropanoate, [(3S,6S,7R,8R)- 8-benzyl-3-[(3-isobutoxycarbonyloxy-4-methoxy-pyridine-2-carbonyl)amino]-6-methyl-4,9-dioxo- 1 ,5-dioxonan-7-yl] 2-methylpropanoate, [(3S,6S,7R,8R)-8-benzyl-3-[[3-(1 ,3-benzodioxol-5- ylmethoxy)-4-methoxy-pyridine-2-carbonyl]amino]-6-methyl-4,9-dioxo-1 ,5-dioxonan-7-yl] 2- methylpropanoate; (3S,6S,7R,8R)-3-[[(3-hydroxy-4-methoxy-2-pyridinyl)carbonyl]amino]- 6-methyl-4,9-dioxo-8-(phenylmethyl)-1 ,5-dioxonan-7-yl 2-methylpropanoate

inhibitors of complex II (e. g. carboxamides): benodanil, benzovindiflupyr, bixafen, boscalid, carboxin, fenfuram, fluopyram, flutolanil, fluxapyroxad, furametpyr, isopyrazam, mepronil, oxycarboxin, penflufen, penthiopyrad, sedaxane, tecloftalam, thifluzamide, N-(4'- trifluoromethylthiobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1 H-pyrazole-4-carboxamide, N-(2- (1 ,3,3-trimethyl-butyl)-phenyl)-1 ,3-dimethyl-5-fluoro-1 H-pyrazole-4-carboxamide,

3- (difluoromethyl)-1 -methyl-N-(1 ,1 ,3-trimethylindan-4-yl)pyrazole-4-carboxamide,

3-(trifluoromethyl)-1 -methyl-N-(1 ,1 ,3-trimethylindan-4-yl)pyrazole-4-carboxamide, 1 ,3-dimethyl- N-(1 ,1 ,3-trimethylindan-4-yl)pyrazole-4-carboxamide, 3-(trifluoromethyl)-1 ,5-dimethyl-N-(1 ,1 ,3- trimethylindan-4-yl)pyrazole-4-carboxamide, 3-(difluoromethyl)-1 ,5-dimethyl-N-(1 ,1 ,3- trimethylindan-4-yl)pyrazole-4-carboxamide, 1 ,3,5-trimethyl-N-(1 ,1 ,3-trimethylindan-4- yl)pyrazole-4-carboxamide;

- other respiration inhibitors (e.g. complex I, uncouplers): diflumetorim, (5,8-difluoro- quinazolin-4-yl)-{2-[2-fluoro-4-(4-trifluoromethylpyridin-2-yloxy)-phenyl]-ethyl}-amine; nitrophenyl derivates: binapacryl, dinobuton, dinocap, fluazinam; ferimzone; organometal compounds: fentin salts, such as fentin-acetate, fentin chloride or fentin hydroxide; ametoctradin; and silthiofam;

B) Sterol biosynthesis inhibitors (SBI fungicides)

C14 demethylase inhibitors (DMI fungicides): triazoles: azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, oxpoconazole, paclobutrazole, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole,

1 -[re/-(2S;3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)-oxiranylmethyl]-5-thiocyanato-1 H- [1 ,2,4]triazole, 2-[re/-(2S;3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)-oxiranylmethyl]- 2H-[1 ,2,4]triazole-3-thiol; imidazoles: imazalil, pefurazoate, prochloraz, triflumizol; pyrimidines, pyridines and piperazines: fenarimol, nuarimol, pyrifenox, triforine;

Delta14-reductase inhibitors: aldimorph, dodemorph, dodemorph-acetate, fenpropimorph, tridemorph, fenpropidin, piperalin, spiroxamine;

Inhibitors of 3-keto reductase: fenhexamid;

C) Nucleic acid synthesis inhibitors

- phenylamides or acyl amino acid fungicides: benalaxyl, benalaxyl-M, kiralaxyl, metalaxyl, metalaxyl-M (mefenoxam), ofurace, oxadixyl;

others: hymexazole, octhilinone, oxolinic acid, bupirimate, 5-fluorocytosine, 5-fluoro-2-(p- tolylmethoxy)pyrimidin-4-amine, 5-fluoro-2-(4-fluorophenylmethoxy)pyrimidin-4-amine;

D) Inhibitors of cell division and cytoskeleton

- tubulin inhibitors, such as benzimidazoles, thiophanates: benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate-methyl; triazolopyrimidines: 5-chloro-7-(4-methyl- piperidin-1 -yl)-6-(2,4,6-trifluorophenyl)-[1 ,2,4]triazolo[1 ,5-a]pyrimidine

other cell division inhibitors: diethofencarb, ethaboxam, pencycuron, fluopicolide, zoxamide, metrafenone, pyriofenone;

E) Inhibitors of amino acid and protein synthesis

methionine synthesis inhibitors (anilino-pyrimidines): cyprodinil, mepanipyrim,

pyrimethanil;

protein synthesis inhibitors: blasticidin-S, kasugamycin, kasugamycin hydrochloride- hydrate, mildiomycin, streptomycin, oxytetracyclin, polyoxine, validamycin A;

F) Signal transduction inhibitors

MAP / histidine kinase inhibitors: fluoroimid, iprodione, procymidone, vinclozolin, fenpiclonil, fludioxonil; G protein inhibitors: quinoxyfen;

G) Lipid and membrane synthesis inhibitors

Phospholipid biosynthesis inhibitors: edifenphos, iprobenfos, pyrazophos, isoprothiolane; lipid peroxidation: dicloran, quintozene, tecnazene, tolclofos-methyl, biphenyl, chloroneb, etridiazole;

phospholipid biosynthesis and cell wall deposition: dimethomorph, flumorph,

mandipropamid, pyrimorph, benthiavalicarb, iprovalicarb, valifenalate and N-(1 -(1 -(4-cyano- phenyl)ethanesulfonyl)-but-2-yl) carbamic acid-(4-fluorophenyl) ester;

compounds affecting cell membrane permeability and fatty acides: propamocarb, propamocarb-hydrochlorid

fatty acid amide hydrolase inhibitors: oxathiapiprolin;

H) Inhibitors with Multi Site Action

inorganic active substances: Bordeaux mixture, copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate, sulfur;

- thio- and dithiocarbamates: ferbam, mancozeb, maneb, metam, metiram, propineb, thiram, zineb, ziram;

organochlorine compounds (e.g. phthalimides, sulfamides, chloronitriles): anilazine, chlorothalonil, captafol, captan, folpet, dichlofluanid, dichlorophen, hexachlorobenzene, pentachlorphenole and its salts, phthalide, tolylfluanid, N-(4-chloro-2-nitro-phenyl)-N-ethyl-4- methyl-benzenesulfonamide;

guanidines and others: guanidine, dodine, dodine free base, guazatine, guazatine- acetate, iminoctadine, iminoctadine-triacetate, iminoctadine-tris(albesilate), dithianon, 2,6- dimethyl-1 H,5H-[1 ,4]dithiino[2,3-c:5,6-c']dipyrrole-1 ,3,5,7(2H,6H)-tetraone;

I) Cell wall synthesis inhibitors

- inhibitors of glucan synthesis: validamycin, polyoxin B; melanin synthesis inhibitors:

pyroquilon, tricyclazole, carpropamid, dicyclomet, fenoxanil;

J) Plant defence inducers

acibenzolar-S-methyl, probenazole, isotianil, tiadinil, prohexadione-calcium;

phosphonates: fosetyl, fosetyl-aluminum, phosphorous acid and its salts;

K) Unknown mode of action

bronopol, chinomethionat, cyflufenamid, cymoxanil, dazomet, debacarb, diclomezine, difenzoquat, difenzoquat-methylsulfate, diphenylamin, fenpyrazamine, flumetover, flusulfamide, flutianil, methasulfocarb, nitrapyrin, nitrothal-isopropyl, oxathiapiprolin, 2-[3,5- bis(difluoromethyl)-1 H-pyrazol-1 -yl]-1 -[4-(4-{5-[2-(prop-2-yn-1 -yloxy)phenyl]-4,5-dihydro-1 ,2- oxazol-3-yl}-1 ,3-thiazol-2-yl)piperidin-1 -yljethanone, 2-[3,5-bis(difluoromethyl)-1 H-pyrazol-1 -yl]- 1 -[4-(4-{5-[2-fluoro-6-(prop-2-yn-1 -yloxy)phenyl]-4,5-dihydro-1 ,2-oxazol-3-yl}-1 ,3-thiazol-2- yl)piperidin-1 -yl]ethanone, 2-[3,5-bis(difluoromethyl)-1 H-pyrazol-1 -yl]-1 -[4-(4-{5-[2-chloro-6- (prop-2-yn-1 -yloxy)phenyl]-4,5-dihydro-1 ,2-oxazol-3-yl}-1 ,3-thiazol-2-yl)piperidin-1 -yl]ethanone, oxin-copper, proquinazid, tebufloquin, tecloftalam, triazoxide, 2-butoxy-6-iodo-3-propylchromen- 4-one, N-(cyclopropylmethoxyimino-(6-difluoro-methoxy-2,3-difluoro-phenyl)-methyl)-2-phenyl acetamide, N'-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methyl formamidine, N'-(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methyl formamidine, N'-(2-methyl-5-trifluoromethyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N- methyl formamidine, N'-(5-difluoromethyl-2-methyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N- ethyl-N-methyl formamidine, methoxy-acetic acid 6-tert-butyl-8-fluoro-2,3-dimethyl-quinolin-4-yl ester, 3-[5-(4-methylphenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine, 3-[5-(4-chloro-phenyl)-2,3- dimethyl-isoxazolidin-3-yl]-pyridine (pyrisoxazole),

N-(6-methoxy-pyridin-3-yl) cyclopropanecarboxylic acid amide, 5-chloro-1 -(4,6-dimethoxy- pyrimidin-2-yl)-2-methyl-1 H-benzoimidazole, 2-(4-chloro-phenyl)-

N-[4-(3,4-dimethoxy-phenyl)-isoxazol-5-yl]-2-prop-2-ynyloxy-acetamide;

L) Antifungal biocontrol agents, plant bioactivators: Ampelomyces quisqualis (e.g. AQ 10® from Intrachem Bio GmbH & Co. KG, Germany), Aspergillus flavus (e.g. AFLAGUARD® from Syngenta, CH), Aureobasidium pullulans (e.g. BOTECTOR® from bio-ferm GmbH, Germany), Bacillus pumilus (e.g. NRRL Accession No. B-30087 in SONATA® and BALLAD® Plus from AgraQuest Inc., USA), Bacillus subtilis (e.g. isolate NRRL-Nr. B-21661 in RHAPSODY®, SERENADE® MAX and SERENADE® ASO from AgraQuest Inc., USA), Bacillus subtilis var. amyloliquefaciens FZB24 (e.g. TAEGRO® from Novozyme Biologicals, Inc., USA), Candida oleophila I-82 (e.g. ASPIRE® from Ecogen Inc., USA), Candida saitoana (e.g. BIOCURE® (in mixture with lysozyme) and BIOCOAT® from Micro Flo Company, USA (BASF SE) and Arysta), Chitosan (e.g. ARMOUR-ZEN from BotriZen Ltd., NZ), Clonostachys rosea f. catenulata, also named Gliocladium catenulatum (e.g. isolate J1446: PRESTOP® from Verdera, Finland), Coniothyrium minitans (e.g. CONTANS® from Prophyta, Germany), Cryphonectria parasitica (e.g. Endothia parasitica from CNICM, France), Cryptococcus albidus (e.g. YIELD PLUS® from Anchor Bio-Technologies, South Africa), Fusarium oxysporum (e.g. BIOFOX® from S.I.A.P.A., Italy, FUSACLEAN® from Natural Plant Protection, France), Metschnikowia fructicola (e.g.

SHEMER® from Agrogreen, Israel), Microdochium dimerum (e.g. ANTIBOT® from Agrauxine, France), Phlebiopsis gigantea (e.g. ROTSOP® from Verdera, Finland), Pseudozyma flocculosa (e.g. SPORODEX® from Plant Products Co. Ltd., Canada), Pythium oligandrum DV74 (e.g. POLYVERSUM® from Remeslo SSRO, Biopreparaty, Czech Rep.), Reynoutria sachlinensis (e.g. REGALIA® from Marrone Biolnnovations, USA), Talaromyces flavus V1 17b (e.g.

PROTUS® from Prophyta, Germany), Trichoderma asperellum SKT-1 (e.g. ECO-HOPE® from Kumiai Chemical Industry Co., Ltd., Japan), T. atroviride LC52 (e.g. SENTINEL® from Agrimm Technologies Ltd, NZ), T. harzianum T "-22 (e.g. PLANTSHIELD® der Firma BioWorks Inc., USA), T. harzianum JH 35 (e.g. ROOT PRO® from Mycontrol Ltd., Israel), T. harzianum T-39 (e.g. TRICHODEX® and TRICHODERMA 2000® from Mycontrol Ltd., Israel and Makhteshim Ltd., Israel), T. harzianum and T. viride (e.g. TRICHOPEL from Agrimm Technologies Ltd, NZ), T. harzianum ICC012 and T. viride ICC080 (e.g. REMEDIER® WP from Isagro Ricerca, Italy), T. polysporum and T. harzianum (e.g. BINAB® from BINAB Bio-Innovation AB, Sweden), T.

stromaticum (e.g. TRICOVAB® from C.E.P.L.A.C., Brazil), T. virens GL-21 (e.g. SOILGARD® from Certis LLC, USA), T. viride (e.g. TRIECO® from Ecosense Labs. (India) Pvt. Ltd., Indien, BIO-CURE® F from T. Stanes & Co. Ltd., Indien), T. v/'r/'c/e TV1 (e.g. T. viride TV1 from

Agribiotec srl, Italy), Ulocladium oudemansii HRU3 (e.g. BOTRY-ZEN® from Botry-Zen Ltd, NZ); M) Growth regulators

abscisic acid, amidochlor, ancymidol, 6-benzylaminopurine, brassinolide, butralin, chlormequat (chlormequat chloride), choline chloride, cyclanilide, daminozide, dikegulac, dimethipin, 2,6- dimethylpuridine, ethephon, flumetralin, flurprimidol, fluthiacet, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid , maleic hydrazide, mefluidide, mepiquat (mepiquat chloride), naphthaleneacetic acid, N-6-benzyladenine, paclobutrazol, prohexadione (prohexadione- calcium), prohydrojasmon, thidiazuron, triapenthenol, tributyl phosphorotrithioate,

2,3,5-tri-iodobenzoic acid , trinexapac-ethyl and uniconazole;

N) Herbicides

- acetamides: acetochlor, alachlor, butachlor, dimethachlor, dimethenamid, flufenacet, mefenacet, metolachlor, metazachlor, napropamide, naproanilide, pethoxamid, pretilachlor, propachlor, thenylchlor;

amino acid derivatives: bilanafos, glyphosate, glufosinate, sulfosate;

aryloxyphenoxypropionat.es: clodinafop, cyhalofop-butyl, fenoxaprop, fluazifop, haloxyfop, metamifop, propaquizafop, quizalofop, quizalofop-P-tefuryl;

Bipyridyls: diquat, paraquat;

(thio)carbamates: asulam, butylate, carbetamide, desmedipham, dimepiperate, eptam (EPTC), esprocarb, molinate, orbencarb, phenmedipham, prosulfocarb, pyributicarb, thiobencarb, triallate;

- cyclohexanediones: butroxydim, clethodim, cycloxydim, profoxydim, sethoxydim, tepraloxydim, tralkoxydim;

dinitroanilines: benfluralin, ethalfluralin, oryzalin, pendimethalin, prodiamine, trifluralin; diphenyl ethers: acifluorfen, aclonifen, bifenox, diclofop, ethoxyfen, fomesafen, lactofen, oxyfluorfen;

- hydroxybenzonitriles: bomoxynil, dichlobenil, ioxynil;

imidazolinones: imazamethabenz, imazamox, imazapic, imazapyr, imazaquin,

imazethapyr;

phenoxy acetic acids: clomeprop, 2,4-dichlorophenoxyacetic acid (2,4-D), 2,4-DB, dichlorprop, MCPA, MCPA-thioethyl, MCPB, Mecoprop;

- pyrazines: chloridazon, flufenpyr-ethyl, fluthiacet, norflurazon, pyridate;

pyridines: aminopyralid, clopyralid, diflufenican, dithiopyr, fluridone, fluroxypyr, picloram, picolinafen, thiazopyr;

sulfonyl ureas: amidosulfuron, azimsulfuron, bensulfuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, foramsulfuron, halosulfuron, imazosulfuron, iodosulfuron, mesosulfuron, metazosulfuron, metsulfuron-methyl, nicosulfuron, oxasulfuron, primisulfuron, prosulfuron, pyrazosulfuron, rimsulfuron, sulfometuron, sulfosulfuron, thifensulfuron, triasulfuron, tribenuron, trifloxysulfuron, triflusulfuron, tritosulfuron, 1 -((2-chloro-6-propyl-imidazo[1 ,2-b]pyridazin-3-yl)sulfonyl)-3-(4,6- d i methoxy-pyri m id i n-2-yl) u rea ;

- triazines: ametryn, atrazine, cyanazine, dimethametryn, ethiozin, hexazinone, metamitron, metribuzin, prometryn, simazine, terbuthylazine, terbutryn, triaziflam; ureas: chlorotoluron, daimuron, diuron, fluometuron, isoproturon, linuron, metha- benzthiazuron,tebuthiuron;

other acetolactate synthase inhibitors: bispyribac-sodium, cloransulam-methyl, diclosulam, florasulam, flucarbazone, flumetsulam, metosulam, ortho-sulfamuron, penoxsulam,

propoxycarbazone, pyribambenz-propyl, pyribenzoxim, pyriftalid, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyroxasulfone, pyroxsulam;

others: amicarbazone, aminotriazole, anilofos, beflubutamid, benazolin,

bencarbazone,benfluresate, benzofenap, bentazone, benzobicyclon, bicyclopyrone, bromacil, bromobutide, butafenacil, butamifos, cafenstrole, carfentrazone, cinidon-ethyl, chlorthal, cinmethylin, clomazone, cumyluron, cyprosulfamide, dicamba, difenzoquat, diflufenzopyr, Drechslera monoceras, endothal, ethofumesate, etobenzanid, fenoxasulfone, fentrazamide, flumiclorac-pentyl, flumioxazin, flupoxam, flurochloridone, flurtamone, indanofan, isoxaben, isoxaflutole, lenacil, propanil, propyzamide, quinclorac, quinmerac, mesotrione, methyl arsonic acid, naptalam, oxadiargyl, oxadiazon, oxaziclomefone, pentoxazone, pinoxaden, pyraclonil, pyraf I uf en-ethyl, pyrasulfotole, pyrazoxyfen, pyrazolynate, quinoclamine, saflufenacil, sulcotrione, sulfentrazone, terbacil, tefuryltrione, tembotrione, thiencarbazone, topramezone, (3-[2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1 -yl)- phenoxy]-pyridin-2-yloxy)-acetic acid ethyl ester, 6-amino-5-chloro-2-cyclopropyl-pyrimidine-4- carboxylic acid methyl ester, 6-chloro-3-(2-cyclopropyl-6-methyl-phenoxy)-pyridazin-4-ol, 4- amino-3-chloro-6-(4-chloro-phenyl)-5-fluoro-pyridine-2-carboxylic acid, 4-amino-3-chloro-6-(4- chloro-2-fluoro-3-methoxy-phenyl)-pyridine-2-carboxylic acid methyl ester, and 4-amino-3- chloro-6-(4-chloro-3-dimethylamino-2-fluoro-phenyl)-pyridine-2-carboxylic acid methyl ester. O) Insecticides

organo(thio)phosphates: acephate, azamethiphos, azinphos-methyl, chlorpyrifos, chlorpyrifos-methyl, chlorfenvinphos, diazinon, dichlorvos, dicrotophos, dimethoate, disulfoton, ethion, fenitrothion, fenthion, isoxathion, malathion, methamidophos, methidathion, methyl- parathion, mevinphos, monocrotophos, oxydemeton-methyl, paraoxon, parathion, phenthoate, phosalone, phosmet, phosphamidon, phorate, phoxim, pirimiphos-methyl, profenofos, prothiofos, sulprophos, tetrachlorvinphos, terbufos, triazophos, trichlorfon;

- carbamates: alanycarb, aldicarb, bendiocarb, benfuracarb, carbaryl, carbofuran, carbosulfan, fenoxycarb, furathiocarb, methiocarb, methomyl, oxamyl, pirimicarb, propoxur, thiodicarb, triazamate;

pyrethroids: allethrin, bifenthrin, cyfluthrin, cyhalothrin, cyphenothrin, cypermethrin, alpha- cypermethrin, beta-cypermethrin, zeta-cypermethrin, deltamethrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, imiprothrin, lambda-cyhalothrin, permethrin, prallethrin, pyrethrin I and II, resmethrin, silafluofen, tau-fluvalinate, tefluthrin, tetramethrin, tralomethrin, transfluthrin, profluthrin, dimefluthrin;

insect growth regulators: a) chitin synthesis inhibitors: benzoylureas: chlorfluazuron, cyramazin, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron; buprofezin, diofenolan, hexythiazox, etoxazole, clofentazine; b) ecdysone antagonists: halofenozide, methoxyfenozide, tebufenozide, azadirachtin; c) juvenoids: pyriproxyfen, methoprene, fenoxycarb; d) lipid biosynthesis inhibitors: spirodiclofen, spiromesifen, spirotetramat;

nicotinic receptor agonists/antagonists compounds: clothianidin, dinotefuran,

flupyradifurone, imidacloprid, thiamethoxam, nitenpyram, acetamiprid, thiacloprid, 1 -2-chloro- thiazol-5-ylmethyl)-2-nitrimino-3,5-dimethyl-[1 ,3,5]triazinane;

GABA antagonist compounds: endosulfan, ethiprole, fipronil, vaniliprole, pyrafluprole, pyriprole, 5-amino-1 -(2,6-dichloro-4-methyl-phenyl)-4-sulfinamoyl-1 H-pyrazole-3-carbothioic acid amide;

macrocyclic lactone insecticides: abamectin, emamectin, milbemectin, lepimectin, spinosad, spinetoram;

mitochondrial electron transport inhibitor (METI) I acaricides: fenazaquin, pyridaben, tebufenpyrad, tolfenpyrad, flufenerim;

METI II and III compounds: acequinocyl, fluacyprim, hydramethylnon;

Uncouplers: chlorfenapyr;

- oxidative phosphorylation inhibitors: cyhexatin, diafenthiuron, fenbutatin oxide, propargite; moulting disruptor compounds: cryomazine;

mixed function oxidase inhibitors: piperonyl butoxide;

sodium channel blockers: indoxacarb, metaflumizone;

ryanodine receptor inhibitors: chlorantraniliprole, cyantraniliprole, flubendiamide, N-[4,6- dichloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5- (trifluoromethyl)pyrazole-3-carboxamide; N-[4-chloro-2-[(diethyl-lambda-4- sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3- carboxamide; N-[4-chloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]- 2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; N-[4,6-dichloro-2-[(di-2-propyl- lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3- carboxamide; N-[4,6-dichloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro- 2-pyridyl)-5-(difluoromethyl)pyrazole-3-carboxamide; N-[4,6-dibromo-2-[(di-2-propyl-lambda- 4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3- carboxamide; N-[4-chloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-6-cyano-phenyl]- 2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; N-[4,6-dibromo-2-[(diethyl- lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3- carboxamide;

others: benclothiaz, bifenazate, cartap, flonicamid, pyridalyl, pymetrozine, sulfur, thiocyclam, cyenopyrafen, flupyrazofos, cyflumetofen, amidoflumet, imicyafos, bistrifluron, pyrifluquinazon and l .l '- S^R^aR.eS.eaS.^R.^aS.^bSH-^- cyclopropylacetyl)oxy]methyl]-1 ,3,4,4a,5,6,6a,12,12a,12b-decahydro-12-hydroxy-4,6a,12b- trimethyl-1 1 -oxo-9-(3-pyridinyl)-2H,1 1 H-naphtho[2,1 -b]pyrano[3,4-e]pyran-3,6-diyl]

cyclopropaneacetic acid ester. The present invention furthermore relates to agrochemical compositions comprising a mixture of at least one compound I (component 1 ) and at least one further active substance useful for plant protection, e. g. selected from the groups A) to O) (component 2), in particular one further fungicide, e. g. one or more fungicide from the groups A) to L), as described above, and if desired one suitable solvent or solid carrier. Those mixtures are of particular interest, since many of them at the same application rate show higher efficiencies against harmful fungi.

Furthermore, combating harmful fungi with a mixture of compounds I and at least one fungicide from groups A) to L), as described above, is more efficient than combating those fungi with individual compounds I or individual fungicides from groups A) to L). By applying compounds I together with at least one active substance from groups A) to O) a synergistic effect can be obtained, i.e. more then simple addition of the individual effects is obtained (synergistic mixtures).

This can be obtained by applying the compounds I and at least one further active substance simultaneously, either jointly (e. g. as tank-mix) or seperately, or in succession, wherein the time interval between the individual applications is selected to ensure that the active substance applied first still occurs at the site of action in a sufficient amount at the time of application of the further active substance(s). The order of application is not essential for working of the present invention.

In binary mixtures, i.e. compositions according to the invention comprising one compound I (component 1 ) and one further active substance (component 2), e. g. one active substance from groups A) to O), the weight ratio of component 1 and component 2 generally depends from the properties of the active substances used, usually it is in the range of from 1 :100 to 100:1 , regularly in the range of from 1 :50 to 50:1 , preferably in the range of from 1 :20 to 20:1 , more preferably in the range of from 1 :10 to 10:1 and in particular in the range of from 1 :3 to 3:1 . In ternary mixtures, i.e. compositions according to the invention comprising one compound I (component 1 ) and a first further active substance (component 2) and a second further active substance (component 3), e. g. two active substances from groups A) to O), the weight ratio of component 1 and component 2 depends from the properties of the active substances used, preferably it is in the range of from 1 :50 to 50:1 and particularly in the range of from 1 :10 to 10:1 , and the weight ratio of component 1 and component 3 preferably is in the range of from 1 :50 to 50:1 and particularly in the range of from 1 :10 to 10:1.

Preference is also given to mixtures comprising a compound I (component 1 ) and at least one active substance selected from group A) (component 2) and particularly selected from azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, orysastrobin, picoxystrobin, pyraclostrobin, trifloxystrobin; famoxadone, fenamidone; benzovindiflupyr, bixafen, boscalid, fluopyram, fluxapyroxad, isopyrazam, penflufen, penthiopyrad, sedaxane; ametoctradin, cyazofamid, fluazinam, fentin salts, such as fentin acetate.

Preference is given to mixtures comprising a compound of formula I (component 1 ) and at least one active substance selected from group B) (component 2) and particularly selected from cyproconazole, difenoconazole, epoxiconazole, fluquinconazole, flusilazole, flutriafol, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, triadimefon, triadimenol, tebuconazole, tetraconazole, triticonazole, prochloraz, fenarimol, triforine;

dodemorph, fenpropimorph, tridemorph, fenpropidin, spiroxamine; fenhexamid. Preference is given to mixtures comprising a compound of formula I (component 1 ) and at least one active substance selected from group C) (component 2) and particularly selected from metalaxyl, (metalaxyl-M) mefenoxam, ofurace.

Preference is given to mixtures comprising a compound of formula I (component 1 ) and at least one active substance selected from group D) (component 2) and particularly selected from benomyl, carbendazim, thiophanate-methyl, ethaboxam, fluopicolide, zoxamide, metrafenone, pyriofenone.

Preference is also given to mixtures comprising a compound I (component 1 ) and at least one active substance selected from group E) (component 2) and particularly selected from cyprodinil, mepanipyrim, pyrimethanil.

Preference is also given to mixtures comprising a compound I (component 1 ) and at least one active substance selected from group F) (component 2) and particularly selected from iprodione, fludioxonil, vinclozolin, quinoxyfen.

Preference is also given to mixtures comprising a compound I (component 1 ) and at least one active substance selected from group G) (component 2) and particularly selected from dimethomorph, flumorph, iprovalicarb, benthiavalicarb, mandipropamid, propamocarb.

Preference is also given to mixtures comprising a compound I (component 1 ) and at least one active substance selected from group H) (component 2) and particularly selected from copper acetate, copper hydroxide, copper oxychloride, copper sulfate, sulfur, mancozeb, metiram, propineb, thiram, captafol, folpet, chlorothalonil, dichlofluanid, dithianon.

Preference is also given to mixtures comprising a compound I (component 1 ) and at least one active substance selected from group I) (component 2) and particularly selected from

carpropamid and fenoxanil.

Preference is also given to mixtures comprising a compound I (component 1 ) and at least one active substance selected from group J) (component 2) and particularly selected from acibenzolar-S-methyl, probenazole, tiadinil, fosetyl, fosetyl-aluminium, H3PO3 and salts thereof. Preference is also given to mixtures comprising a compound I (component 1 ) and at least one active substance selected from group K) (component 2) and particularly selected from cymoxanil, proquinazid and A/-methyl-2-{1 -[(5-methyl-3-trifluoromethyl-1 H-pyrazol-1 -yl)-acetyl]- piperidin-4-yl}-A/-[(1 R)-1 ,2,3,4-tetrahydronaphthalen-1 -yl]-4-thiazolecarboxamide.

Preference is also given to mixtures comprising a compound I (component 1 ) and at least one active substance selected from group L) (component 2) and particularly selected from Bacillus subtilis strain NRRL No. B-21661 , Bacillus pumilus strain NRRL No. B-30087 and Ulocladium oudemansii .

Accordingly, the present invention furthermore relates to compositions comprising one compound I (component 1 ) and one further active substance (component 2), which further active substance is selected from the column "Component 2" of the lines C-1 to C-381 of Table C.

A further embodiment relates to the compositions C-1 to C-381 listed in Table C, where a row of Table C corresponds in each case to a fungicidal composition comprising one of the in the present specification individualized compounds of formula I (component 1 ) and the respective further active substance from groups A) to O) (component 2) stated in the row in question. Preferably, the compositions described comprise the active substances in synergistically effective amounts.

Table C: Composition comprising one indiviualized compound I and one further active substance from groups A) to O)

Mixture Component 1 Component 2

C-1 one individualized compound I Azoxystrobin

C-2 one individualized compound I Coumethoxystrobin

C-3 one individualized compound I Coumoxystrobin

C-4 one individualized compound I Dimoxystrobin

C-5 one individualized compound I Enestroburin

C-6 one individualized compound I Fenaminstrobin

C-1 one individualized compound I Fenoxystrobin/Flufenoxystrobin

C-8 one individualized compound I Fluoxastrobin

C-9 one individualized compound I Kresoxim-methyl

C-10 one individualized compound I Metominostrobin

C-1 1 one individualized compound I Orysastrobin

C-12 one individualized compound I Picoxystrobin

C-13 one individualized compound I Pyraclostrobin

C-14 one individualized compound I Pyrametostrobin

C-15 one individualized compound I Pyraoxystrobin

C-16 one individualized compound I Pyribencarb

C-17 one individualized compound I Trifloxystrobin

C-18 one individualized compound I Triclopyricarb/Chlorodincarb

2-[2-(2,5-dimethyl-phenoxymethyl)-

C-19 one individualized compound I phenyl]-3-methoxy-acrylic acid methyl ester

2-(2-(3-(2,6-dichlorophenyl)-1 -methyl-

C-20 one individualized compound I allylideneaminooxymethyl)-phenyl)-

2-methoxyimino-N-methyl-acetamide

C-21 one individualized compound I Benalaxyl

C-22 one individualized compound I Benalaxyl-M

C-23 one individualized compound I Benodanil

C-24 one individualized compound I Benzovindiflupyr

C-25 one individualized compound I Bixafen

C-26 one individualized compound I Boscalid

C-27 one individualized compound I Carboxin

C-28 one individualized compound I Fenfuram

C-29 one individualized compound I Fenhexamid

C-30 one individualized compound I Flutolanil

C-31 one individualized compound I Fluxapyroxad Mixture Component 1 Component 2

C-32 one individualized compound I Furametpyr

C-33 one individualized compound I Isopyrazam

C-34 one individualized compound I Isotianil

C-35 one individualized compound I Kiralaxyl

C-36 one individualized compound I Mepronil

C-37 one individualized compound I Metalaxyl

C-38 one individualized compound I Metalaxyl-M

C-39 one individualized compound I Ofurace

C-40 one individualized compound I Oxadixyl

C-41 one individualized compound I Oxycarboxin

C-42 one individualized compound I Penflufen

C-43 one individualized compound I Penthiopyrad

C-44 one individualized compound I Sedaxane

C-45 one individualized compound I Tecloftalam

C-46 one individualized compound I Thifluzamide

C-47 one individualized compound I Tiadinil

2-Amino-4-methyl-thiazole-5-carboxylic

C-48 one individualized compound I

acid anilide

N-(4'-trifluoromethylthiobiphenyl-2-yl)-

C-49 one individualized compound I 3- difluoromethyl-1 -methyl-1 H-pyrazole-

4- carboxamide

N-(2-(1 ,3,3-trimethyl-butyl)-phenyl)-

C-50 one individualized compound I 1 ,3-dimethyl-5-fluoro-1 H-pyrazole- 4-carboxamide

3-(difluoromethyl)-1 -methyl-N-(1 ,1 ,3-tri-

C-51 one individualized compound I methylindan-4-yl)pyrazole-4-carbox- amide

3-(trifluoromethyl)-1 -methyl-N-(1 ,1 ,3-tri-

C-52 one individualized compound I methylindan-4-yl)pyrazole-4-carbox- amide

1 ,3-dimethyl-N-(1 ,1 ,3-trimethylindan-

C-53 one individualized compound I

4-yl)pyrazole-4-carboxamide

3- (trifluoromethyl)-1 ,5-dimethyl-

C-54 one individualized compound I N-(1 ,1 ,3-trimethylindan-4-yl)pyrazole-

4- carboxamide

3- (difluoromethyl)-1 ,5-dimethyl-

C-55 one individualized compound I N-(1 ,1 ,3-trimethylindan-4-yl)pyrazole-

4- carboxamide

1 ,3,5-trimethyl-N-(1 ,1 ,3-trimethylindan-

C-56 one individualized compound I

4-yl)pyrazole-4-carboxamide Mixture Component 1 Component 2

C-57 one individualized compound I Dimethomorph

C-58 one individualized compound I Flumorph

C-59 one individualized compound I Pyrimorph

C-60 one individualized compound I Flumetover

C-61 one individualized compound I Fluopicolide

C-62 one individualized compound I Fluopyram

C-63 one individualized compound I Zoxamide

C-64 one individualized compound I Carpropamid

C-65 one individualized compound I Diclocymet

C-66 one individualized compound I Mandipropamid

C-67 one individualized compound I Oxytetracyclin

C-68 one individualized compound I Silthiofam

N-(6-methoxy-pyridin-3-yl)

C-69 one individualized compound I

cyclopropanecarboxylic acid amide

C-70 one individualized compound I Azaconazole

C-71 one individualized compound I Bitertanol

C-72 one individualized compound I Bromuconazole

C-73 one individualized compound I Cyproconazole

C-74 one individualized compound I Difenoconazole

C-75 one individualized compound I Diniconazole

C-76 one individualized compound I Diniconazole-M

C-77 one individualized compound I Epoxiconazole

C-78 one individualized compound I Fenbuconazole

C-79 one individualized compound I Fluquinconazole

C-80 one individualized compound I Flusilazole

C-81 one individualized compound I Flutriafol

C-82 one individualized compound I Hexaconazol

C-83 one individualized compound I Imibenconazole

C-84 one individualized compound I Ipconazole

C-85 one individualized compound I Metconazole

C-86 one individualized compound I Myclobutanil

C-87 one individualized compound I Oxpoconazol

C-88 one individualized compound I Paclobutrazol

C-89 one individualized compound I Penconazole

C-90 one individualized compound I Propiconazole

C-91 one individualized compound I Prothioconazole

C-92 one individualized compound I Simeconazole

C-93 one individualized compound I Tebuconazole

C-94 one individualized compound I Tetraconazole

C-95 one individualized compound I Triadimefon Mixture Component 1 Component 2

C-96 one individualized compound I Triadimenol

C-97 one individualized compound I Triticonazole

C-98 one individualized compound I Uniconazole

1 - [re/-(2S;3R)-3-(2-chlorophenyl)-

C-99 one individualized compound I 2- (2,4-difluorophenyl)-oxiranylmethyl]- 5-thiocyanato-1 H-[1 ,2,4]triazole,

2-[re/-(2S;3R)-3-(2-chlorophenyl)-

C-100 one individualized compound I 2-(2,4-difluorophenyl)-oxiranylmethyl]-

2H-[1 ,2,4]triazole-3-thiol

C-101 one individualized compound I Cyazofamid

C-102 one individualized compound I Amisulbrom

C-103 one individualized compound I Imazalil

C-104 one individualized compound I Imazalil-sulfate

C-105 one individualized compound I Pefurazoate

C-106 one individualized compound I Prochloraz

C-107 one individualized compound I Triflumizole

C-108 one individualized compound I Benomyl

C-109 one individualized compound I Carbendazim

C-1 10 one individualized compound I Fuberidazole

C-1 1 1 one individualized compound I Thiabendazole

C-1 12 one individualized compound I Ethaboxam

C-1 13 one individualized compound I Etridiazole

C-1 14 one individualized compound I Hymexazole

2-(4-Chloro-phenyl)-N-[4-(3,4-dimeth-

C-1 15 one individualized compound I oxy-phenyl)-isoxazol-5-yl]-2-prop-2-yn- yloxy-acetamide

C-1 16 one individualized compound I Fluazinam

C-1 17 one individualized compound I Pyrifenox

3-[5-(4-Chloro-phenyl)-2,3-dimethyl-is-

C-1 18 one individualized compound I

oxazolidin-3-yl]-pyridine (Pyrisoxazole)

3-[5-(4-Methyl-phenyl)-2,3-dimethyl-

C-1 19 one individualized compound I

isoxazolidin-3-yl]-pyridine

C-120 one individualized compound I Bupirimate

C-121 one individualized compound I Cyprodinil

C-122 one individualized compound I 5-Fluorocytosine

5-Fluoro-2-(p-tolylmethoxy)pyrimidin-

C-123 one individualized compound I

4-amine

5-Fluoro-2-(4-fluorophenylmethoxy)-

C-124 one individualized compound I

pyrimidin-4-amine

C-125 one individualized compound I Diflumetorim Mixture Component 1 Component 2

(5,8-Difluoroquinazolin-4-yl)-{2-[2-fluo-

C-126 one individualized compound I ro-4-(4-trifluoromethylpyridin-2-yloxy)- phenyl]-ethyl}-amine

C-127 one individualized compound I Fenarimol

C-128 one individualized compound I Ferimzone

C-129 one individualized compound I Mepanipyrim

C-130 one individualized compound I Nitra pyrin

C-131 one individualized compound I Nuarimol

C-132 one individualized compound I Pyrimethanil

C-133 one individualized compound I Triforine

C-134 one individualized compound I Fenpiclonil

C-135 one individualized compound I Fludioxonil

C-136 one individualized compound I Aldimorph

C-137 one individualized compound I Dodemorph

C-138 one individualized compound I Dodemorph-acetate

C-139 one individualized compound I Fenpropimorph

C-140 one individualized compound I Tridemorph

C-141 one individualized compound I Fenpropidin

C-142 one individualized compound I Fluoroimid

C-143 one individualized compound I Iprodione

C-144 one individualized compound I Procymidone

C-145 one individualized compound I Vinclozolin

C-146 one individualized compound I Famoxadone

C-147 one individualized compound I Fenamidone

C-148 one individualized compound I Flutianil

C-149 one individualized compound I Octhilinone

C-150 one individualized compound I Probenazole

C-151 one individualized compound I Fenpyrazamine

C-152 one individualized compound I Acibenzolar-S-methyl

C-153 one individualized compound I Ametoctradin

C-154 one individualized compound I Amisulbrom

[(3S,6S,7R,8R)-8-benzyl-3-[(3-isobuty- ryloxymethoxy-4-methoxypyridine-

C-155 one individualized compound I

2-carbonyl)amino]-6-methyl-4,9-dioxo- [1 ,5]dioxonan-7-yl] 2-methylpropanoate

[(3S,6S,7R,8R)-8-benzyl-3-[(3-acetoxy- 4-methoxy-pyridine-2-carbonyl)amino]-

C-156 one individualized compound I

6-methyl-4,9-dioxo-1 ,5-dioxonan-7-yl] 2-methylpropanoate Mixture Component 1 Component 2

[(3S,6S,7R,8R)-8-benzyl-3-[[3-(acet- oxymethoxy)-4-methoxy-pyridine-

C-157 one individualized compound I

2-carbonyl]amino]-6-methyl-4,9-dioxo- 1 ,5-dioxonan-7-yl] 2-methylpropanoate

[(3S,6S,7R,8R)-8-benzyl-3-[(3-isobut- oxycarbonyloxy-4-methoxy-pyridine-

C-158 one individualized compound I

2-carbonyl)amino]-6-methyl-4,9-dioxo- 1 ,5-dioxonan-7-yl] 2-methylpropanoate

[(3S,6S,7R,8R)-8-benzyl-3-[[3-(1 ,3-ben- zodioxol-5-ylmethoxy)-4-methoxy-pyri-

C-159 one individualized compound I dine-2-carbonyl]amino]-6-methyl-4,9-di- oxo-1 ,5-dioxonan-7-yl] 2-methylpropanoate

(3S,6S,7R,8R)-3-[[(3-hydroxy-4-meth- oxy-2-pyridinyl)carbonyl]amino]-

C-160 one individualized compound I

6-methyl-4,9-dioxo-8-(phenylmethyl)- 1 ,5-dioxonan-7-yl 2-methylpropanoate

C-161 one individualized compound I Anilazin

C-162 one individualized compound I Blasticidin-S

C-163 one individualized compound I Captafol

C-164 one individualized compound I Captan

C-165 one individualized compound I Chinomethionat

C-166 one individualized compound I Dazomet

C-167 one individualized compound I Debacarb

C-168 one individualized compound I Diclomezine

C-169 one individualized compound I Difenzoquat,

C-170 one individualized compound I Difenzoquat-methylsulfate

C-171 one individualized compound I Fenoxanil

C-172 one individualized compound I Folpet

C-173 one individualized compound I Oxolinsaure

C-174 one individualized compound I Piperalin

C-175 one individualized compound I Proquinazid

C-176 one individualized compound I Pyroquilon

C-177 one individualized compound I Quinoxyfen

C-178 one individualized compound I Triazoxid

C-179 one individualized compound I Tricyclazole

2-Butoxy-6-iodo-3-propyl-chromen-4-

C-180 one individualized compound I

one

5-Chloro-1 -(4,6-dimethoxy-pyrimidin-2-

C-181 one individualized compound I

yl)-2-methyl-1 H-benzoimidazole Mixture Component 1 Component 2

5- Chloro-7-(4-methyl-piperidin-1 -yl)-

C-182 one individualized compound I 6- (2,4,6-trifluoro-phenyl)-[1 ,2,4]tri- azolo[1 ,5-a]pyrimidine

C-183 one individualized compound I Ferbam

C-184 one individualized compound I Mancozeb

C-185 one individualized compound I Maneb

C-186 one individualized compound I Metam

C-187 one individualized compound I Methasulphocarb

C-188 one individualized compound I Metiram

C-189 one individualized compound I Propineb

C-190 one individualized compound I Thiram

C-191 one individualized compound I Zineb

C-192 one individualized compound I Ziram

C-193 one individualized compound I Diethofencarb

C-194 one individualized compound I Benthiavalicarb

C-195 one individualized compound I Iprovalicarb

C-196 one individualized compound I Propamocarb

C-197 one individualized compound I Propamocarb hydrochlorid

C-198 one individualized compound I Valifenalate

N-(1 -(1 -(4-cyanophenyl)ethanesulfon-

C-199 one individualized compound I yl)-but-2-yl) carbamic acid-(4-fluoro- phenyl) ester

C-200 one individualized compound I Dodine

C-201 one individualized compound I Dodine free base

C-202 one individualized compound I Guazatine

C-203 one individualized compound I Guazatine-acetate

C-204 one individualized compound I Iminoctadine

C-205 one individualized compound I Iminoctadine-triacetate

C-206 one individualized compound I Iminoctadine-tris(albesilate)

C-207 one individualized compound I Kasugamycin

C-208 one individualized compound I Kasugamycin-hydrochloride-hydrate

C-209 one individualized compound I Polyoxine

C-210 one individualized compound I Streptomycin

C-21 1 one individualized compound I Validamycin A

C-212 one individualized compound I Binapacryl

C-213 one individualized compound I Dicloran

C-214 one individualized compound I Dinobuton

C-215 one individualized compound I Dinocap

C-216 one individualized compound I Nitrothal-isopropyl

C-217 one individualized compound I Tecnazen Mixture Component 1 Component 2

C-218 one individualized compound I Fentin salts

C-219 one individualized compound I Dithianon

2,6-dimethyl-1 H,5H-[1 ,4]dithiino

C-220 one individualized compound I [2,3-c:5,6-c']dipyrrole-

1 ,3,5,7(2H,6H)-tetraone

C-221 one individualized compound I Isoprothiolane

C-222 one individualized compound I Edifenphos

C-223 one individualized compound I Fosetyl, Fosetyl-aluminium

C-224 one individualized compound I Iprobenfos

Phosphorous acid (H3PO3) and

C-225 one individualized compound I

derivatives

C-226 one individualized compound I Pyrazophos

C-227 one individualized compound I Tolclofos-methyl

C-228 one individualized compound I Chlorothalonil

C-229 one individualized compound I Dichlofluanid

C-230 one individualized compound I Dichlorophen

C-231 one individualized compound I Flusulfamide

C-232 one individualized compound I Hexachlorbenzene

C-233 one individualized compound I Pencycuron

C-234 one individualized compound I Pentachlorophenol and salts

C-235 one individualized compound I Phthalide

C-236 one individualized compound I Quintozene

C-237 one individualized compound I Thiophanate Methyl

C-238 one individualized compound I Tolylfluanid

N-(4-chloro-2-nitro-phenyl)-N-ethyl-

C-239 one individualized compound I

4-methyl-benzenesulfonamide

C-240 one individualized compound I Bordeaux mixture

C-241 one individualized compound I Copper acetate

C-242 one individualized compound I Copper hydroxide

C-243 one individualized compound I Copper oxychloride

C-244 one individualized compound I basic Copper sulfate

C-245 one individualized compound I Sulfur

C-246 one individualized compound I Biphenyl

C-247 one individualized compound I Bronopol

C-248 one individualized compound I Cyflufenamid

C-249 one individualized compound I Cymoxanil

C-250 one individualized compound I Diphenylamin

C-251 one individualized compound I Metrafenone

C-252 one individualized compound I Pyriofenone

C-253 one individualized compound I Mildiomycin Mixture Component 1 Component 2

C-254 one individualized compound I Oxin-copper

C-255 one individualized compound I Oxathiapiprolin

2-[3,5-bis(difluoromethyl)-1 H-pyrazol-1 - y|]-1 -[4-(4-{5-[2-(prop-2-yn-1 -yloxy)phe-

C-256 one individualized compound I

nyl]-4,5-dihydro-1 ,2-oxazol-3-yl}-1 ,3-thi- azol-2-yl)piperidin-1 -yl]ethanone

2- [3,5-bis(difluoromethyl)-1 H-pyrazol- 1 -yl]-1 -[4-(4-{5-[2-fluoro-6-(prop-2-yn-

C-257 one individualized compound I 1 -yloxy)phenyl]-4,5-dihydro-1 ,2-oxazol-

3- yl}-1 ,3-thiazol-2-yl)piperidin-1 -yl]- ethanone

2- [3,5-bis(difluoromethyl)-1 H-pyrazol- 1 -yl]-1 -[4-(4-{5-[2-chloro-6-(prop-2-yn-

C-258 one individualized compound I 1 -yloxy)phenyl]-4,5-dihydro-1 ,2-oxazol-

3- yl}-1 ,3-thiazol-2-yl)piperidin-1 -yl]- ethanone

C-259 one individualized compound I Prohexadione calcium

C-260 one individualized compound I Spiroxamine

C-261 one individualized compound I Tebufloquin

C-262 one individualized compound I Tolylfluanid

N-(Cyclopropylmethoxyimino-(6-

C-263 one individualized compound I difluoromethoxy-2,3-difluoro-phenyl)- methyl)-2-phenyl acetamide

N'-(4-(4-chloro-3-trifluoromethyl-

C-264 one individualized compound I phenoxy)-2,5-dimethyl-phenyl)-N-ethyl- N-methyl formamidine

N'-(4-(4-fluoro-3-trifluoromethyl-

C-265 one individualized compound I phenoxy)-2,5-dimethyl-phenyl)-N-ethyl- N-methyl formamidine

N'-(2-methyl-5-trifluoromethyl-4-(3-tri-

C-266 one individualized compound I methylsilanyl-propoxy)-phenyl)-N-ethyl- N-methyl formamidine

N'-(5-difluoromethyl-2-methyl-4-(3-tri-

C-267 one individualized compound I methylsilanyl-propoxy)-phenyl)-N-ethyl- N-methyl formamidine

Methoxy-acetic acid 6-tert-butyl-8-

C-268 one individualized compound I

fluoro-2,3-dimethyl-quinolin-4-yl ester

C-269 one individualized compound I Bacillus subtilis NRRL No. B-21661

C-270 one individualized compound I Bacillus pumilus NRRL No. B-30087

C-271 one individualized compound I Ulocladium oudemansii Mixture Component 1 Component 2

C-272 one individualized compound I Carbaryl

C-273 one individualized compound I Carbofuran

C-274 one individualized compound I Carbosulfan

C-275 one individualized compound I Methomylthiodicarb

C-276 one individualized compound I Bifenthrin

C-277 one individualized compound I Cyfluthrin

C-278 one individualized compound I Cypermethrin

C-279 one individualized compound I alpha-Cypermethrin

C-280 one individualized compound I zeta-Cypermethrin

C-281 one individualized compound I Deltamethrin

C-282 one individualized compound I Esfenvalerate

C-283 one individualized compound I Lambda-cyhalothrin

C-284 one individualized compound I Permethrin

C-285 one individualized compound I Tefluthrin

C-286 one individualized compound I Diflubenzuron

C-287 one individualized compound I Flufenoxuron

C-288 one individualized compound I Lufenuron

C-289 one individualized compound I Teflubenzuron

C-290 one individualized compound I Spirotetramate

C-291 one individualized compound I Clothianidin

C-292 one individualized compound I Dinotefuran

C-293 one individualized compound I Imidacloprid

C-294 one individualized compound I Thiamethoxam

C-295 one individualized compound I Flupyradifurone

C-296 one individualized compound I Acetamiprid

C-297 one individualized compound I Thiacloprid

C-298 one individualized compound I Endosulfan

C-299 one individualized compound I Fipronil

C-300 one individualized compound I Abamectin

C-301 one individualized compound I Emamectin

C-302 one individualized compound I Spinosad

C-303 one individualized compound I Spinetoram

C-304 one individualized compound I Hydramethylnon

C-305 one individualized compound I Chlorfenapyr

C-306 one individualized compound I Fenbutatin oxide

C-307 one individualized compound I Indoxacarb

C-308 one individualized compound I Metaflumizone

C-309 one individualized compound I Flonicamid

C-310 one individualized compound I Flubendiamide

C-31 1 one individualized compound I Chlorantraniliprole Mixture Component 1 Component 2

C-312 one individualized compound I Cyantraniliprole

N-[4,6-dichloro-2-[(diethyl-lambda- 4-sulfanylidene)carbamoyl]-phenyl]-

C-313 one individualized compound I

2-(3-chloro-2-pyridyl)-5-(trifluorometh- yl)pyrazole-3-carboxamide

N-[4-chloro-2-[(diethyl-lambda-4-sul- fanylidene)carbamoyl]-6-methyl-phe-

C-314 one individualized compound I

nyl]-2-(3-chloro-2-pyridyl)-5-(trifluoro- methyl)pyrazole-3-carboxamide

N-[4-chloro-2-[(di-2-propyl-lambda- 4-sulfanylidene)carbamoyl]-6-methyl-

C-315 one individualized compound I

phenyl]-2-(3-chloro-2-pyridyl)-5-(tri- fluoromethyl)pyrazole-3-carboxamide

N-[4,6-dichloro-2-[(di-2-propyl-lambda- 4-sulfanylidene)carbamoyl]-phenyl]-

C-316 one individualized compound I

2-(3-chloro-2-pyridyl)-5-(trifluoro- methyl)pyrazole-3-carboxamide

N-[4,6-dichloro-2-[(diethyl-lambda- 4-sulfanylidene)carbamoyl]-phenyl]-

C-317 one individualized compound I

2-(3-chloro-2-pyridyl)-5-(difluoro- methyl)pyrazole-3-carboxamide

N-[4,6-dibromo-2-[(di-2-propyl-lambda- 4-sulfanylidene)carbamoyl]-phenyl]-2-

C-318 one individualized compound I

(3-chloro-2-pyridyl)-5-(trifluoromethyl)- pyrazole-3-carboxamide

N-[4-chloro-2-[(di-2-propyl-lambda- 4-sulfanylidene)carbamoyl]-6-cyano-

C-319 one individualized compound I

phenyl]-2-(3-chloro-2-pyridyl)-5-(tri- fluoromethyl)pyrazole-3-carboxamide

N-[4,6-dibromo-2-[(diethyl-lambda- 4-sulfanylidene)carbamoyl]-phenyl]-

C-320 one individualized compound I

2-(3-chloro-2-pyridyl)-5-(trifluorometh- yl)pyrazole-3-carboxamide

C-321 one individualized compound I Cyflumetofen

C-322 one individualized compound I Acetochlor

C-323 one individualized compound I Dimethenamid

C-324 one individualized compound I metolachlor

C-325 one individualized compound I Metazachlor

C-326 one individualized compound I Glyphosate

C-327 one individualized compound I Glufosinate Mixture Component 1 Component 2

C-328 one individualized compound I Sulfosate

C-329 one individualized compound I Clodinafop

C-330 one individualized compound I Fenoxaprop

C-331 one individualized compound I Fluazifop

C-332 one individualized compound I Haloxyfop

C-333 one individualized compound I Paraquat

C-334 one individualized compound I Phenmedipham

C-335 one individualized compound I Clethodim

C-336 one individualized compound I Cycloxydim

C-337 one individualized compound I Profoxydim

C-338 one individualized compound I Sethoxydim

C-339 one individualized compound I Tepraloxydim

C-340 one individualized compound I Pendimethalin

C-341 one individualized compound I Prodiamine

C-342 one individualized compound I Trifluralin

C-343 one individualized compound I Acifluorfen

C-344 one individualized compound I Bromoxynil

C-345 one individualized compound I Imazamethabenz

C-346 one individualized compound I Imazamox

C-347 one individualized compound I Imazapic

C-348 one individualized compound I Imazapyr

C-349 one individualized compound I Imazaquin

C-350 one individualized compound I Imazethapyr

C-351 one individualized compound I 2,4-Dichlorophenoxyacetic acid (2,4-D)

C-352 one individualized compound I Chloridazon

C-353 one individualized compound I Clopyralid

C-354 one individualized compound I Fluroxypyr

C-355 one individualized compound I Picloram

C-356 one individualized compound I Picolinafen

C-357 one individualized compound I Bensulfuron

C-358 one individualized compound I Chlorimuron-ethyl

C-359 one individualized compound I Cyclosulfamuron

C-360 one individualized compound I lodosulfuron

C-361 one individualized compound I Mesosulfuron

C-362 one individualized compound I Metsulfuron-methyl

C-363 one individualized compound I Nicosulfuron

C-364 one individualized compound I Rimsulfuron

C-365 one individualized compound I Triflusulfuron

C-366 one individualized compound I Atrazine

C-367 one individualized compound I Hexazinone Mixture Component 1 Component 2

C-368 one individualized compound I Diuron

C-369 one individualized compound I Florasulam

C-370 one individualized compound I Pyroxasulfone

C-371 one individualized compound I Bentazone

C-372 one individualized compound I Cinidon-ethyl

C-373 one individualized compound I Cinmethylin

C-374 one individualized compound I Dicamba

C-375 one individualized compound I Diflufenzopyr

C-376 one individualized compound I Quinclorac

C-377 one individualized compound I Quinmerac

C-378 one individualized compound I Mesotrione

C-379 one individualized compound I Saflufenacil

C-380 one individualized compound I Topramezone

1 ,1 '-[(3S,4R,4aR,6S,6aS,12R,12aS,

12bS)-4-[[(2-cyclopropylacetyl)oxy]me- thyl]-1 ,3,4,4a,5,6,6a,12,12a,12b-deca-

C-381 one individualized compound I hydro-12-hydroxy-4,6a,12b-trimethyl-

1 1 -oxo-9-(3-pyridinyl)-2H,1 1 H-naph- tho[2,1 -b]pyrano[3,4-e]pyran-3,6-diyl] cyclopropaneacetic acid ester

The active substances referred to as component 2, their preparation and their activity against harmful fungi is known (cf.: http://www.alanwood.net/pesticides/); these substances are commercially available. The compounds described by lUPAC nomenclature, their preparation and their fungicidal activity are also known (cf. Can. J. Plant Sci. 48(6), 587-94, 1968; EP-A 141 317; EP-A 152 031 ; EP-A 226 917; EP-A 243 970; EP-A 256 503; EP-A 428 941 ; EP- A 532 022; EP-A 1 028 125; EP-A 1 035 122; EP-A 1 201 648; EP-A 1 122 244,

JP 2002316902; DE 19650197; DE 10021412; DE 102005009458; US 3,296,272;

US 3,325,503; WO 98/46608; WO 99/14187; WO 99/24413; WO 99/27783; WO 00/29404; WO 00/46148; WO 00/65913; WO 01/54501 ; WO 01/56358; WO 02/22583; WO 02/40431 ; WO 03/10149; WO 03/1 1853; WO 03/14103; WO 03/16286; WO 03/53145; WO 03/61388; WO 03/66609; WO 03/74491 ; WO 04/49804; WO 04/83193; WO 05/120234; WO 05/123689; WO 05/123690; WO 05/63721 ; WO 05/87772; WO 05/87773; WO 06/15866; WO 06/87325; WO 06/87343; WO 07/82098; WO 07/90624, WO 1 1/028657, WO2012/168188, WO

2007/006670, PCT/EP2012/065650 and PCT/EP2012/065651 ).

The mixtures of active substances can be prepared as compositions comprising besides the active ingridients at least one inert ingredient by usual means, e. g. by the means given for the compositions of compounds I.

Concerning usual ingredients of such compositions reference is made to the explanations given for the compositions containing compounds I. The mixtures of active substances according to the present invention are suitable as fungicides, as are the compounds of formula I. They are distinguished by an outstanding effectiveness against a broad spectrum of phytopathogenic fungi, especially from the classes of the

Ascomycetes, Basidiomycetes, Deuteromycetes and Peronosporomycetes (syn. Oomycetes). In addition, it is refered to the explanations regarding the fungicidal activity of the compounds and the compositions containing compounds I, respectively.

I. Synthesis examples With appropriate modification of the starting materials, the procedures given in the synthesis examples below were used to obtain further compounds I. The compounds produced in this manner are listed in Table I below including corresponding physical data.

Example 1 : Preparation of 4-[[4-(trifluoromethyl)-2-pyridyl]oxy]phenol

To a solution of 4-hydroxyphenol (20 g, 180 mmol) in A/-methyl-2-pyrrolidone (500 ml.) at 10°C was added sodium hydride (7.3 g, 180 mmol). The reaction mixture was stirred at room temperature for 30 min, then a solution of 2-chloro-4-trifluoromethylpyridine (27 g, 150 mmol) in A/-methyl-2-pyrrolidone (100 ml.) was added and the solution was stirred for 2 h at 80°C. The reaction contents were then poured into water, extracted with methyl ferf-butylether (3x ). The combined organic layers were washed with water, dried over sodium sulfate and the solvent was the removed in vacuo. The crude residue was purified by flash silica gel column

chromatography (cyclohexane/ethyl acetate) to afford a 30% (12 g, 50 mmol) yield of 4-[[4- (trifluoromethyl)-2-pyridyl]oxy]phenol.

Example 2: Preparation of 1 -[4-[[4-(trifluoromethyl)-2-pyridyl]oxy]phenoxy]propan-2 -amine hydrochloride

To a solution of 4-[[4-(trifluoromethyl)-2-pyridyl]oxy]phenol (3 g, 10 mmol), ((S)-2-hydroxy-1 - methyl-ethyl)-carbamate (2.3 g, 10 mmol) and triphenylphosphine (3 g, 10 mmol) in

tetrahydrofurane (100 ml.) at 0°C was slowly added diethyl azodicarboxylate (2.5 g, 10 mmol). The reaction solution was stirred overnight at room temperature then directly loaded on a silica gel column eluting with cyclohexane and methyl feri-butylether to afford 2.2 g (5 mmol, 50%) yield of /V-ferf-butyloxycarbonyl-protected 1 -[4-[[4-(trifluoromethyl)-2- pyridyl]oxy]phenoxy]propan-2 -amine. To a solution of this material (1 .7 g, 4.1 mmol) in dioxane (20 ml.) was added 4 M HCI in dioxane (10 ml_). The solution was left overnight to stir at room temperature which resulted in precipitation of 1 -[4-[[4-(trifluoromethyl)-2- pyridyl]oxy]phenoxy]propan-2-amine hydrochloride. The hydrochloride was filtered and washed with methyl ferf-butylether to provide 88% (1.4 g, 3.6 mmol) of the white powdery product.

Example 3: Preparation of 6-chloro-5-methoxy-N-[1 -methyl-2-[4-[[4-(trifluoromethyl)-2- pyridyl]oxy]phenoxy]ethyl]pyrimidin-4-amine (I-8)

To a solution of amine (320 mg, 0.8 mmol) in A/-methyl-2-pyrrolidone (6 ml.) was added diisopropylethylamine (270 mg, 2 mmol). The solution was stirred for 5 min at room temperature at which time 4,6-dichloro-5-methoxypyrimidine (150 mg, 0.8 mmol) was added. The reaction mixture was stirred at 80°C overnight then allowed to cool to room temperature. Water was added and the resulting mixture was extracted with methyl feri-butylether (3x). The combined organic layers were washed with water, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by HPLC to provide 139 mg (0.3 mmol, 37%) of the light yellow oily product.

The compounds listed in Table I have been prepared in an analogous manner.

Table I: Compounds 1-1 to 1-18 of formula I as defined herein, wherein Ra2, R, R1 and R2 in each case are hydrogen, Y is -O- and the group -O-Het is bound on the phenyl ring in ortho-position relative to the CR1R2-0-moiety.

Figure imgf000066_0001

* The position of Rb on the phenyl ring is defined relative to the CR1R2-0-moiety bound to the phenyl ring as being in ortho (o-) or meta (m-) position; n = 0 indicates that no substituent Rb is present on the phenyl ring. m.p. = melting point (°C).

HPLC: HPLC-column Kinetex XB C18 1 ,7μ (50 x 2,1 mm); eluent: acetonitrile / water + 0.1 % TFA (gradient from 5:95 to 100 : 0 in 1.5 min at 60°C, flow gradient from 0.8 to 1.0 ml/min in 1 .5 min). MS: Quadrupol Electrospray lonisation, 80 V (positive mode).

II. Biological examples for fungicidal activity

The fungicidal action of the compounds I was demonstrated by the following experiments: Glass house trials

The spray solutions were prepared in several steps: The stock solution were prepared: a mixture of acetone and/or dimethylsulfoxide and the wetting agent/emulsifier Wettol, which is based on ethoxylated alkylphenoles, in a relation (volume) solvent-emulsifier of 99 to 1 was added to 25 mg of the compound to give a total of 5 ml. Water was then added to total volume of 100 ml. This stock solution was diluted with the described solvent-emulsifier-water mixture to the given concentration. After the final cultivation period, the extent of fungal attack on the leaves was visually assessed as % diseased leaf area.

Use example 1 : Control of late blight on tomatoes caused by Phytophthora infestans

Young seedlings of tomato plants were grown in pots. These plants were sprayed to run-off with an aqueous suspension, containing the concentration of active ingredient or their mixture mentioned in the table below. The next day, the treated plants were inoculated with an aqueous suspension of sporangia of Phytophthora infestans. After inoculation, the trial plants were immediately transferred to a humid chamber. After 6 days at 18 to 20°C and a relative humidity close to 100% the extent of fungal attack on the leaves was visually assessed as % diseased leaf area.

In this test, the plants which had been treated with 250 ppm of the active compound

1-1 , I-2, I-5, I-7, I-8, I-9, 1-10, 1-1 1 , 1-12, 1-13, 1-14, 1-15, 1-16, 1-17 or 1-18 showed a diseased leaf area of at most 20%, whereas the untreated plants showed 76% diseased leaf area.

Use example 2: Preventative control of leaf blotch on wheat caused by Septoria tritici

Leaves of pot-grown wheat seedling were sprayed to run-off with an aqueous suspension of the active compound or their mixture, prepared as described. The plants were allowed to air-dry. At the following day the plants were inoculated with an aqueous spore suspension of Septoria tritici. Then the trial plants were immediately transferred to a humid chamber at 18 to 22°C and a relative humidity close to 100%. After 4 days the plants were transferred to a chamber with 18 to 22°C and a relative humidity close to 70%. After 4 weeks the extent of fungal attack on the leaves was visually assessed as % diseased leaf area.

In this test, the plants which had been treated with 250 ppm of the active compound

I-2, I-3, I-4, I-7, I-8, I-9, 1-10 or 1-1 1 showed a diseased leaf area of at most 20%, whereas the untreated plants showed 97% diseased leaf area.

Use example 3: Preventative control of brown rust on wheat caused by Puccinia recondita. The first two developed leaves of pot-grown wheat seedling were sprayed to run-off with an aqueous suspension, containing the concentration of active ingredient or their mixture as described below. The next day the plants were inoculated with spores of Puccinia recondita. To ensure the success the artificial inoculation, the plants were transferred to a humid chamber without light and a relative humidity of 95 to 99% and 20 to 24°C for 24 h. Then the trial plants were cultivated for 6 days in a greenhouse chamber at 20 to 24°C and a relative humidity between 65 and 70%. The extent of fungal attack on the leaves was visually assessed as % diseased leaf area.

In this test, the plants which had been treated with 250 ppm of the active compound

1-1 , I-2, I-5, I-6, I-7, I-8 or 1-10 showed a diseased leaf area of at most 20%, whereas the untreated plants showed 86% diseased leaf area. Use example 4: Protective control of soy bean rust on soy beans caused by Phakopsora pachyrhizi Leaves of pot-grown soy bean seedlings were sprayed to run-off with an aqueous suspension, containing the concentration of active ingredient or their mixture as described below. The plants were allowed to air-dry. The trial plants were cultivated for 1 day in a greenhouse chamber at 23 to 27°C and a relative humidity between 60 and 80%. Then the plants were inoculated with spores of Phakopsora pachyrhizi. To ensure the success the artificial inoculation, the plants were transferred to a humid chamber with a relative humidity of about 95% and 20 to 24°C for 24 h. The trial plants were cultivated for fourteen days in a greenhouse chamber at 23 to 27°C and a relative humidity between 60 and 80%. The extent of fungal attack on the leaves was visually assessed as % diseased leaf area.

In this test, the plants which had been treated with 250 ppm of the active compound

I-5, I-7, 1-12, 1-13, 1-15 or 1-16 showed a diseased leaf area of at most 10%, whereas the untreated plants showed 93% diseased leaf area. Use example 5: Preventative fungicidal control of Botrytis cinerea on leaves of green pepper Young seedlings of green pepper were grown in pots to the 4 to 5 leaf stage. These plants were sprayed to run-off with an aqueous suspension, containing the concentration of active ingredient or their mixture mentioned in the table below. The next day the plants were inoculated with a aqueous biomalt solution containing the spore suspension of Botrytis cinerea. Then the plants were immediately transferred to a humid chamber and kept for 5 days at 22 to 24°C and a relative humidity close to 100 %.

In this test, the plants which had been treated with 250 ppm of the active compound

I-3, I-6 or I-9 showed a diseased leaf area of at most 15%, whereas the untreated plants showed 90% diseased leaf area.

Use example 6: Control of late blight on tomatoes caused by Phytophthora infestans

Young seedlings of tomato plants were grown in pots. These plants were sprayed to run-off with an aqueous suspension, containing the concentration of active ingredient or their mixture mentioned in the table below. After seven days the treated plants were inoculated with an aqueous suspension of sporangia of Phytophthora infestans. After inoculation, the trial plants were immediately transferred to a humid chamber and kept for 6 days at 18 to 20°C and a relative humidity close to 100%.

In this test, the plants which had been treated with 250 ppm of the active compound

1-12, 1-13 or 1-14 showed a diseased leaf area of at most 15%, whereas the untreated plants showed 79% diseased leaf area.

Claims

We claim:
1 . Compounds of formula I
Figure imgf000069_0001
wherein:
Ra2, Ra5 , Ra6 independently of each other are hydrogen, halogen, CN , NO2, OH, SH, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, C1-C4- haloalkylthio, Ci-C4-alkylsulfinyl, Ci-C4-haloalkylsulfinyl, Ci-C4-alkylsulfonyl, C1-C4- haloalkylsulfonyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy, C2-C4-alk- enyl, C2-C4-alkynyl, C2-C4-haloalkenyl, C2-C4-haloalkynyl, Cs-Cs-cycloalkyl, C3-C8- cycloalkyloxy, C3-C8-cycloalkyl-Ci-C4-alkyl, NRARB, C(=0)R', C(=NOR")R"' or - C(=NH)-0-R"';
RA, RB independently of one another are hydrogen, Ci-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, phenyl, benzyl, Cs-Cs-cycloalkyl, C3-Cs-cycloalkenyl or -(C=0)- R';
R' is hydrogen, OH, NH2, Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, C2-C4-alkynyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylamino or di(Ci-C4-alkyl)amino;
R" is hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, C2-C4-alkynyl or C 1 -C4-a I koxy-C 1 -C4-a I ky I ,
R'" is hydrogen or Ci-C4-alkyl;
R is hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C1-C4- alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, CN, CH2CN, NRARB or CH2-0-C(=0)R';
R1 , R2 independently of each other are hydrogen, CN , Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4- alkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4- alkynyl, C2-C4-haloalkynyl, Cs-Cs-cycloalkyl, C3-Cs-cycloalkyl-Ci-C4-alkyl, C3-C8- cycloalkyloxy, NRARB, C(=0)R', C(=NOR")R"', -C(=NH)-0-R"' or benzyl wherein the phenyl moiety of benzyl is unsubstituted or carries 1 , 2 , 3, 4, or 5 substituents se- lected from the group consisting of CN, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkoxy, Ci-C4-haloalkoxy, (Ci-C4-alkoxy)carbonyl and di(Ci-C4-alkyl)aminocarbonyl; or two radicals R1 and R2 that are bound to the same carbon atom form together with said carbon atom a saturated or partially unsaturated
3-, 4-, 5-, 6-, or 7-membered carbocycle or a saturated or partially unsaturated 3-, 4- , 5-, 6-, or 7-membered heterocycle, wherein the ring member atoms of the abovementioned heterocycle include beside carbon atoms 1 , 2, 3 or 4 heteroatoms selected from the group of N, O and S, and wherein the abovementioned cycle is unsubstituted or carries 1 , 2, 3 or 4 substituents selected from halogen, CN, OH, SH, Ci-C4-alkyl, Ci-C4-alkoxy or Ci-C4-alkylthio; and one or two CH2 groups of the abovementioned cycles may be respectively be replaced by one or two C(=0) or C(=S) groups; is a divalent group selected from -CR3R4-, -C(=0)-, -C(=S)-, -C(=NRD)- and -C(=NORD)-, wherein
RD is hydrogen or Ci-C4-alkyl, and wherein
R3 and R4 independently of each other are hydrogen, CN, Ci-C4-hydroxyalkyl, Ci- C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4- haloalkynyl, Cs-Cs-cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl, Cs-Cs-cycloalkyloxy, NRARB, C(=0)R', C(=NOR")R"',-C(=NH)-0-R"' or benzyl wherein the phenyl moiety of benzyl is unsubstituted or carries 1 , 2 , 3, 4, or 5 substituents selected from the group consisting of CN, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, C1-C4- haloalkoxy, (Ci-C4-alkoxy)carbonyl and di(Ci-C4-alkyl)aminocarbonyl, or two radicals R3 and R4 that are bound to the same carbon atom form together with said carbon atom a saturated or partially unsaturated
3-, 4-, 5-, 6-, or 7-membered carbocycle or a saturated or partially unsaturated 3-, 4- , 5-, 6-, or 7-membered heterocycle, wherein the ring member atoms of the abovementioned heterocycle include beside carbon atoms 1 , 2, 3 or 4 heteroatoms selected from the group of N, O and S, and wherein the abovementioned cycle is unsubstituted or carries 1 , 2, 3 or 4 substituents selected from halogen, CN, OH, SH, Ci-C4-alkyl, Ci-C4-alkoxy or Ci-C4-alkylthio; and one or two CH2 groups of the abovementioned cycles may be respectively replaced by one or two C(=0) or C(=S) groups; n indicates the number of substituents Rb on the phenyl ring and n is 0, 1 , 2, 3 or 4; Rb is halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, NRARB, C(=0)R', C(=NOR")R"' or -C(=NH)-0-R"', it being possible for n = 2, 3 or 4 that Rb are identical or different;
Y is oxygen or a direct bond between Het and the phenyl ring;
Het is a 5- or 6-membered heteroaryl, wherein the ring member atoms of the heteroaryl include besides carbon atoms 1 , 2, 3 or 4 heteroatoms selected from the group of N, O and S and wherein the heteroaryl is unsubstituted or carries 1 , 2, 3 or 4 identical or different groups Rc:
Rc is halogen, CN, N02, NH2, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy,
Ci-C6-haloalkoxy, Ci-C6-alkylamino, di(Ci-C6-alkyl)amino, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfinyl, Ci-C6-haloalkylsulfinyl,
Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, Ci-C6-alkoxy-Ci-C4-alkyl, Ci-C6-haloalkoxy-Ci-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C(=0)R', C(=NOR")R"', Cs-Cs-cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl, phenyl, phenoxy, phenoxy-Ci-C4-alkyl or a 5- or 6-membered heteroaryl, wherein the ring member atoms of the heteroaryl include besides carbon atoms 1 , 2, 3 or 4 heteroatoms selected from the group of N, O and S, and wherein the aforementioned cyclic radicals are unsubstituted or carry 1 , 2, 3 or 4 identical or different substituents Rd:
Rd is halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy or
Ci-C4-haloalkoxy; and the N-oxides and the agriculturally acceptable salts of the compounds of formula I, with the provision that N-[2-[3-(1 -isobutyltetrazol-5-yl)-5-methyl-phenoxy]-1 -methyl- ethyl]pyrimidin-4-amine be excluded.
Compounds according to claim 1 , wherein Ra2, Ra5 and Ra6 independently of each other are halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C1-C4- alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy or (Ci-C4-alkoxy)carbonyl, and it being possible that one or two of Ra2, Ra5 or Ra6 can in addition be hydrogen.
Compounds according to claim 1 or 2, wherein R1 and R2 independently of each other are CN, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy or
Cs-Cs-cycloalkyl.
Compounds according to any one of claims 1 to 3, wherein X is -CH2- Compounds according to any one of claims 1 to 4, wherein X is -C(=0)-.
Compounds according to any one of claims 1 to 5, wherein Het is pyrimidin-2-yl, pyrimidin-3-yl, pyrimidin-4-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, thiazol-2-yl, pyrazin-2- yl, pyridazin-3-yl, 1 ,3,5-triazin-2-yl or 1 ,2,4-triazin-3-yl.
Compounds according to any one of claims 1 to 6, wherein Het carries 1 or 2 radicals Rc which are F, CI, Br, CN, Ci-C2-alkylsulfonyl, Ci-C2-alkoxycarbonyl, aminocarbonyl, C1-C2- alkylaminocarbonyl, di(Ci-C2-alkyl)aminocarbonyl, Ci-C2-alkoxy, CF3, CHF2, OCF3 or
Compounds according to any one of claims 1 to 7, wherein R is hydrogen.
A process for preparing compounds I as defined in claim 1 , wherein X is -CR3R4- or - C(=0)-, which comprises reacting a compound of formula II
Figure imgf000072_0001
wherein Ra2, Ra5 and Ra6 are as defined in claim 1 , Hal is fluorine, chlorine or bromine, with a compound of formula
Figure imgf000072_0002
wherein R, R1, R2, Rb, Y, n and Het are as defined in claim 1 and X is -CR3R4- or -C(=0)- as defined in claim 1 in the presence of a base or a catalyst or a combination of a base and a catalyst in a solvent.
10. An agrochemical composition which comprises an auxiliary and at least one compound of formula I or an N-oxide or an agriculturally acceptable salt thereof, according to any one of claims 1 to 8.
1 1 . An agrochemical composition according to claim 10 comprising at least one further active substance.
12. A method for combating phytopathogenic harmful fungi, which process comprises treating the fungi or the materials, plants, the soil or seeds to be protected against fungal attack, with an effective amount of at least one compound of formula I or an N-oxide or an agriculturally acceptable salt thereof, according to any one of claims 1 to 8.
3. The use of compounds of formula I, their N-oxides or their agriculturally acceptable salts, according to any one of claims 1 to 8 for combating phytopathogenic harmful fungi.
4. Seed treated with a compound of formula I, or an N-oxide or an agriculturally acceptable salt thereof, as defined in any one of claims 1 to 8, in an amount of from 0.1 g to 10 kg per 100 kg of seed.
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