New substituted pyridine compounds for combating phytopathogenic fungi

Abstract

The present invention relates to the compounds of formula (I) w wherein the variables are defined as given in the description and claims. The invention further relates to their use and composition.

Description

[0001] 250444W001

[0002] New substituted pyridine compounds for combating phytopathogenic fungi

[0003] The present invention relates to new substituted pyridine compounds, as well as the N-oxides and the salts thereof, as fungicides, as well as to their use. The invention also relates to the composition comprising at least one compound I, to the method for combating phytopathogenic fungi and to the seed coated with at least one compound of the formula I.

[0004] US 20110136782, WO 2010125782, W02009119089 and JP2011148714, discloses some pyridine compounds and WO 2011037128 discloses some benzodiazepine compounds. However, in many cases, in particular at low application rates, the fungicidal activity of the known compounds is unsatisfactory. Based on this, it was an objective of the present invention to provide compounds having improved activity and / or a broader activity spectrum against phytopathogenic fungi. Another object of the present invention is to provide fungicides with improved toxicological properties or with improved environmental fate properties.

[0005] These and further objects are achieved by the pyridine compounds of formula (I), as defined below, and by their agriculturally suitable salts.

[0006] Accordingly, the present invention relates to the compounds of formula I

[0007]

[0008] (I)

[0009] wherein

[0010] Z is NR9, O, S, SO or SO2;

[0011] w is O or l;

[0012] R1is in each case independently selected from H, halogen, CN, Ci-C6-alkyl, Ci-C6-halogen- alkyl, O-Ci-C6-alkyl, S-Ci-C6-alkyl, 0-Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl;

[0013] R2is in each case independently selected from H, halogen, CN, Ci-C6-alkyl, Ci-C6-halogen- alkyl, O-Ci-C6-alkyl, S-Ci-C6-alkyl, 0-Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl;

[0014] R3is in each case independently selected from H, halogen, CN, Ci-C6-alkyl, Ci-C6-halogen- alkyl, O-Ci-C6-alkyl, S-Ci-C6-alkyl, 0-Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl;

[0015] R4is in each case independently selected from H, halogen, CN, Ci-C6-alkyl, Ci-C6-halogen- alkyl, O-Ci-C6-alkyl, S-Ci-C6-alkyl, 0-Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalky;250444W001

[0016] 2

[0017] R5is in each case independently selected from hydrogen, halogen, CN, Ci-C6-alkyl, Ci-C6- halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, phenyl, benzyl, heterocyclic aromatics and CH2-heterocyclic aromatics where the mentioned aliphatic or aromatic radicals are unsubstituted or carry 1 , 2 or 3 substituents R5a; where each R5ais independently halogen, CN, Ci-C6-alkyl, Ci-C6-halogenalkyl or Ci-C6- alkoxy;

[0018] R6is in each case independently selected from hydrogen, halogen, CN, Ci-C6-alkyl, Ci-C6- halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, phenyl, benzyl, heterocyclic aromatics and CH2-heterocyclic aromatics where the mentioned aliphatic or aromatic radicals are unsubstituted or carry 1 , 2 or 3 substituents R6a; where each R6ais independently halogen, CN, Ci-C6-alkyl, Ci-C6-halogenalkyl or Ci-C6- alkoxy; or

[0019] R5and R6, together with the C atom to which they are bound, form an oxo group (=0); or a thi-oxo group (=S); or

[0020] R5and R6, together with the carbon atom to which they are bound, form a 3-, 4-, 5- or 6-membered saturated carbocyclic ring ora 3-, 4-, 5- or 6-membered saturated heterocyclic ring containing 1, 2 or 3 heteroatoms selected from O and S as ring members; where the carbocyclic or heterocyclic ring is unsubstituted or carries 1 , 2 or 3 substituents R56;

[0021] where each R56is independently halogen, Ci-C6-alkyl or Ci-C6-halogenalkyl;

[0022] R7is in each case independently selected from hydrogen, halogen, CN, Ci-C6-alkyl, Ci-C6- halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, phenyl, benzyl, heterocyclic aromatics and CH2-heterocyclic aromatics where the mentioned aliphatic or aromatic radicals are unsubstituted or carry 1 , 2 or 3 substituents R7a; where each R7ais independently halogen, CN, Ci-C6-alkyl, Ci-C6-halogenalkyl or Ci-C6- alkoxy;

[0023] R8is in each case independently selected from hydrogen, halogen, CN, Ci-C6-alkyl, Ci-C6- halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, phenyl, benzyl, heterocyclic aromatics and CH2-heterocyclic aromatics where the mentioned aliphatic or aromatic radicals are unsubstituted or carry 1 , 2 or 3 substituents R8a; where each R8ais independently halogen, CN, Ci-C6-alkyl, Ci-C6-halogenalkyl or Ci-C6- alkoxy; or

[0024] R7and R8, together with the carbon atom to which they are bound, form an oxo group (=0); or a thioxo group (=S); ora 3-, 4-, 5- or 6-membered saturated carbocyclic ring or a 3-, 4-, 5- or 6-membered saturated heterocyclic ring containing 1 , 2 or 3 heteroatoms selected from O and S as ring members; where the carbocyclic or heterocyclic ring is unsubstituted or carries 1 , 2 or 3 substituents R78,

[0025] where each R78is independently halogen, Ci-C6-alkyl or Ci-C6-halogenalkyl;

[0026] R9is in each case independently selected from H, CN, CH2CN, CH(CH3)CN, CH(=O), - C(=O)Ci-C6-alkyl, -C(=O)C2-C6-alkenyl, -C(=O)C2-C6-alkynyl, -C(=0)C3-C6-cycloalkyl, -250444W001

[0027] 3

[0028] C(=O)-N(H)Ci-C4-alkyl, -C(=O)-N(Ci-C4-alkyl)2, Ci-C6-alkyl, Ci-C6-alkoxy, Ci-C4-halogen- alkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6- alkynyl, C2-C6-halogenalkynyl, -S(=O)2-R9a, five- or six-membered heteroaryl, aryl or benzyl; wherein heteroaryl contains 1 , 2 or 3 heteroatoms selected from N, O and S as ring members; wherein aryl and the phenyl ring in benzyl are unsubstituted or carry 1 , 2, 3, 4 or 5 substituents selected from the group consisting of CN, halogen, OH, Ci-C4-alkyl, Ci- C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy; wherein the phenyl ring in benzyl is unsubstituted or carries 1 , 2 or 3 substituents selected from the group consisting of CN and halogen;

[0029] wherein

[0030] R9ais Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6- alkynyl, C2-C6-halogenalkynyl, phenyl or benzyl, where the phenyl ring in the two last-mentioned radicals is unsubstituted or carries 1 , 2 or 3 substituents each independently selected from the group consisting of halogen, Ci-C6-alkyl, Ci-C6- halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl and C2-C6-halo- genalkynyl;

[0031] X1is in each case independently selected from H, halogen, CN, Ci-C6-alkyl, Ci-C6-halogen- alkyl, O-Ci-C6-alkyl, S-Ci-C6-alkyl, 0-Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, phenyl, benzyl, O-phenyl, O-benzyl;

[0032] X2is in each case independently selected from H, halogen, CN, Ci-C6-alkyl, Ci-C6-halogen- alkyl, O-Ci-C6-alkyl, S-Ci-C6-alkyl, 0-Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, phenyl, benzyl, O-phenyl, O-benzyl;

[0033] wherein

[0034] R2or R3, but not both, is H; and

[0035] with the proviso that if w is 0 and Z is O or S, R1is not Cl and CH3.

[0036] and the N-oxides and the agriculturally acceptable salts thereof as fungicides.

[0037] The / V-oxides may be prepared from the inventive compounds 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. 38(11), 1892-903, 1995); or with inorganic oxidizing agents such as hydrogen peroxide (cf. J. Heterocyc. Chem. 18(7), 1305-8, 1981) or ox-one (cf. J. Am. Chem. Soc. 123(25), 5962-5973, 2001). The oxidation may lead to pure mono- / V-oxides or to a mixture of different N-oxides, which can be separated by conventional methods such as chromatography.

[0038] Agriculturally acceptable salts of the compounds of the formula 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 be substituted with one to four Ci-C4-alkyl substituents and / or one phenyl or benzyl substituent, preferably250444W001

[0039] 4

[0040] diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(Ci-C4-alkyl)sulfonium, and sulfoxo-nium ions, preferably tri(Ci-C4-alkyl)sulfoxonium.

[0041] Anions of acceptable 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.

[0042] Compounds of the formula I bearing only one stereocenter, at the carbon attached to R5, R6, R7, R8, as defined above, can exist only as the enriched stereoisomer. Compounds of the formula I bearing one or several additional stereocenters may exist as one or several stereoisomers. The various stereoisomers include enantiomers, diastereomers, atropisomers arising from restricted rotation about a single bond of asymmetric groups and geometric isomers. They are also a part of the subject matter of the present invention. The person skilled in the art will appreciate that one stereoisomer may be more active and / or may exhibit beneficial effects when enriched relative to the other stereoisomer(s) or when separated from the other stereoisomer(s).

[0043] Additionally, the skilled artisan knows how to separate, enrich, and / or to selectively prepare said stereoisomers. The compounds of the invention may be present as a mixture of stereoisomers, e.g. a racemate, individual stereoisomers, or as an optically active form.

[0044] Compounds of the formula 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.

[0045] In respect of the variables, the embodiments of the intermediates obtained during preparation of compounds I correspond to the embodiments of the compounds of formula I. The term “compounds I” refers to compounds of the formula I.

[0046] In the following, the intermediate compounds are further described. A skilled person will readily understand that the preferences for the substituents, also in particular the ones given in the tables below for the respective substituents, given herein in connection with compounds I apply for the intermediates accordingly. Thereby, the substituents in each case have independently of each other or more preferably in combination the meanings as defined herein.

[0047] 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.

[0048] 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.

[0049] The term "halogen" refers to fluorine, chlorine, bromine and iodine.

[0050] The term "Ci-C6-alkyl" refers to a straight-chained or branched saturated hydrocarbon group250444W001

[0051] 5

[0052] having 1 to 6 carbon atoms, e.g. methyl, ethyl, propyl, 1 -methylethyl, butyl, 1 -methylpropyl, 2-methylpropyl, 1,1 -dimethylethyl, pentyl, 1 -methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dime-thylpropyl, 1 -ethylpropyl, 1,1 -dimethylpropyl, 1,2-dimethylpropyl, hexyl, 1 -methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1 -dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethyl-butyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1 -ethylbutyl, 2-ethylbutyl, 1,1,2-tri-methylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl. Likewise, the term "C2-C4-alkyl" refers to a straight-chained or branched alkyl group having 2 to 4 carbon atoms, such as ethyl, propyl (n-propyl), 1 -methylethyl (iso-propoyl), butyl, 1 -methylpropyl (sec.-butyl), 2-methylpropyl (iso-butyl), 1 ,1 -dimethylethyl (tert. -butyl).

[0053] The term "Ci-C6-halogenalkyl" refers to an alkyl group having 1 or 6 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. Examples are "Ci-C2-halogenalkyl" groups such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1 -chloroethyl, 1-bromoethyl, 1-fluoro-ethyl, 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 or pentafluoroethyl.

[0054] The term "Ci-C6-alkoxy" or “O-Ci-C6-alkyl” refer to a straight-chain or branched alkyl group having 1 to 6 carbon atoms which is bonded via an oxygen, at any position in the alkyl group. Examples are "Ci-C4-alkoxy" groups, such as methoxy, ethoxy, n-propoxy, 1 -methylethoxy, butoxy, 1-methyhpropoxy, 2-methylpropoxy or 1,1 -dimethylethoxy.

[0055] The term "Ci-C6-halogenalkoxy" or “0-Ci-C6-halogenalkyl” refers to a Ci-C6-alkoxy or or “O-Ci-C6-alkyl” radical as defined above, wherein some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above. Examples are "Ci-C4-halogenalkoxy" groups, such as OCH2F, OCHF2, OCF3, OCH2CI, OCHCI2, OCCI3, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chlorothoxy, 2-bromoethoxy, 2-io-doethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluo-roethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, OC2F5, 2-fluoropropoxy, 3-fluoro-propoxy, 2,2-difluoropropoxy, 2,3-difluoro-,propoxy, 2 chloropropoxy, 3-chloropropoxy, 2,3-di-chloropropoxy, 2-bromopropoxy, 3 bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH2-C2F5, OCF2-C2F5, 1-fluoromethyl-2-fluoroethoxy, 1-chloromethyl-2-chloroethoxy, 1-bro-momethyl-2-bromoethoxy, 4-fluorobutoxy, 4- ch loro butoxy, 4-bromobutoxy or nonafluorobutoxy. 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. Examples are "C2-C4-alkenyl" groups, 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. The term "C2-C6-halogenalkenyl" refers to an alkyl group having 2 or 6 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.

[0056] The term "C2-C6-alkenyloxy" refers to a straight-chain or branched alkenyl group having 2 to 6 carbon atoms which is bonded via an oxygen, at any position in the alkenyl group. Examples are "C2-C4-alkenyloxy" groups.

[0057] The term "C2-C6-alkynyl" refers to a straight-chain or branched unsaturated hydrocarbon radical250444W001

[0058] 6

[0059] having 2 to 6 carbon atoms and containing at least one triple bond. Examples are "C2-C4-al-kynyl" groups, such as ethynyl, prop-1 -ynyl, prop-2-ynyl (propargyl), but-1-ynyl, but-2-ynyl, but- 3-ynyl, 1-methyl-prop-2-ynyl.

[0060] The term "C2-C6-halogenalkynyl" refers to an alkyl group having 2 or 6 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.

[0061] The term "C2-C6-alkynyloxy" refers to a straight-chain or branched alkynyl group having 2 to 6 carbon atoms which is bonded via an oxygen, at any position in the alkynyl group. Examples are "C2-C4-alkynyloxy" groups.

[0062] The term "C3-C6-cycloalkyl" refers to monocyclic saturated hydrocarbon radicals having 3 to 6 carbon ring members, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl. Accordingly, a saturated three-, four-, five-, six-, seven-, eight-, nine or ten-membered carbocyclyl or carbocycle is a "C3-Cio-cycloalkyl".

[0063] The term "C3-C6-cycloalkenyl" refers to a monocyclic partially unsaturated 3-, 4- 5- or 6-membered carbocycle having 3 to 6 carbon ring members and at least one double bond, such as cyclopentenyl, cyclopentadienyl, cyclohexadienyl. Accordingly, a partially unsaturated three-, four-, five-, six-, seven-, eight-, nine or ten-membered carbocyclyl or carbocycle is a "C3-Cio-cycloalkenyl".

[0064] The term "C3-C8-cycloalkyl-Ci-C4-alkyl" refers to alkyl having 1 to 4 carbon atoms (as defined above), whereAccording to one hydrogen atom of the alkyl radical is replaced by a cycloalkyl radical having 3 to 8 carbon atoms (as defined above).

[0065] The term “saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine or tenmembered heterocyclyl or heterocycle, wherein the heterocyclyl or heterocycle contains 1, 2, 3 or 4 heteroatoms selected from N, O and S” is to be understood as meaning both saturated and partially unsaturated heterocycles, wherein the ring member atoms of the heterocycle include besides carbon atoms 1 , 2, 3 or 4 heteroatoms independently selected from the group of O, N and S. For example:

[0066] a 3- or 4-membered saturated heterocycle which contains 1 or 2 heteroatoms from the group consisting of O, N and S as ring members such as oxirane, aziridine, thiirane, oxetane, azetidine, thiethane, [1,2]dioxetane, [1,2]dithietane, [1,2]diazetidine; and

[0067] a 5- or 6-membered saturated or partially unsaturated heterocycle which contains 1 , 2 or 3 heteroatoms from the group consisting of O, N 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,

[0068] 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,250444W001

[0069] 7

[0070] 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-dihydrooxazol-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-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl, 1 ,3,5-hexahydrotriazin-2-yl and 1 ,2,4-hexahydrotriazin-3-yl and also the corresponding -ylidene radicals; and

[0071] a 7-membered saturated or partially unsaturated heterocycle such as tetra- and hexahydroazepinyl, such as 2,3,4,5-tetrahydro[1H]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[1H]azepin-1-,-2-,-3-,-4-,-5-,-6-or-7-yl, 2,3,6,7-tetrahydro[1H]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[1H]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 hexa hydro- 1,4-oxazepinyl, tetra- and hexahydro-1, 3-dioxepinyl, tetra- and hexahydro- 1 ,4-dioxepinyl and the corresponding -ylidene radicals.

[0072] The term “substituted” refers to substitued with 1 , 2, 3 or up to the maximum possible number of substituents.

[0073] The term “5-or 6-membered heteroaryl” or “5-or 6-membered heteroaromatic” refers to aromatic ring systems incuding besides carbon atoms, 1 , 2, 3 or 4 heteroatoms independently selected from the group consisting of N, O and S, for example,

[0074] 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

[0075] 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.

[0076] In the following, particular embodiments of the inventive compounds are described. Therein, specific meanings of the respective substituents are further detained, wherein the meanings are in each case on their own but also in any combination with one another, particular embodiments of the present invention.250444W001

[0077] 8

[0078] Furthermore, in respect of the variables, generally, the embodiments of the compounds I also apply to the intermediates.

[0079] According to one embodiment of the compound of formula I, Z is NR9, O, S, SO or SO2.

[0080] According to one preferred embodiment of the compound of formula I, Z is S, O or NR9if w is 0. According to one preferred embodiment of the compound of formula I, Z is S orO ifw is 1. According to one further embodiment of the compound of formula I, Z is NR9ifw is 0.

[0081] According to one further embodiment of the compound of formula I, Z is O.

[0082] According to one further embodiment of the compound of formula I, Z is S.

[0083] According to one further embodiment of the compound of formula I, Z is SO.

[0084] According to one further embodiment of the compound of formula I, Z is SO2.

[0085] According to one embodiment of the compound of formula I, w is 0 or 1.

[0086] According to one preferred embodiment of the compound of formula I, w is 0.

[0087] According to one preferred embodiment of the compound of formula I, w is 1.

[0088] According to one embodiment of the compound of formula I, R1is in each case independently selected from H, halogen, CN, Ci-C6-alkyl, Ci-C6-halogenalkyl, O-Ci-C6-alkyl, S-Ci-C6-alkyl, O-Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl.

[0089] According to still another embodiment of formula I, R1is H.

[0090] According to still another embodiment of formula I, R1is halogen, in particular F, Cl, Br or I, more specifically F, Cl or Br, in particular Br or Cl.

[0091] According to still another embodiment of formula I, R1is F.

[0092] According to still another embodiment of formula I, R1is Cl.

[0093] According to still another embodiment of formula I, R1is Br.

[0094] According to still another embodiment of formula I, R1is CN.

[0095] According to still another embodiment of formula I, R1is Ci-C6-alkyl, in particular Ci-C4-alkyl, such as CH3or C2H5, in particular CH3or CH2CH3.

[0096] According to still another embodiment of formula I, R1is Ci-C6-halogenalkyl, in particular C1-C4-halogenalkyl, such as CF3.

[0097] According to a further specific embodiment of formula I, R1is O-Ci-C6-alkyl, in particular O-C1-C4-alkyl, more specifically Ci-C2-alkoxy. R1is such as OCH3or OCH2CH3.

[0098] According to a further specific embodiment of formula I, R1is S-Ci-C6-alkyl, in particular S-C1-C4-alkyl, more specifically S-Ci-C2-alkyl. R1is such as SCH3or SCH2CH3.

[0099] According to still another embodiment of formula I, R1is 0-Ci-C6-halogenalkyl, in particular O-Ci-C4-halogenalkyl, such as OCF3or OCHF2.

[0100] According to still a further embodiment of formula I, R1is C2-C6-alkenyl, in particular C2-C4-alk-enyl, such as CH=CH2, C(CH3)=CH2, CH2CH=CH2.250444W001

[0101] According to still a further embodiment of formula I, R1is C2-C6-alkynyl or C2-C6-halogenalkynyl, in particular C2-C4-alkynyl or C2-C4-halogenalkynyl, such as CHCH, CH2CHCH, CHCCI, CH2CHCCI, orCCI2CHCCI.

[0102] According to still another embodiment of formula I, R1is C3-C6-cycloalkyl, in particular cyclopropyl or cyclobutyl.

[0103] Particularly preferred embodiments of R1according to the invention are in Table P1 below, wherein each line of lines P1-1 to P1-22 corresponds to one particular embodiment of the invention, wherein P1-1 to P1-22 are also in any combination with one another a preferred embodiment of the present invention. The connection point to the carbon atom, to which R1is bound is marked with

[0104]

[0105] in the drawings.

[0106] Table P1:

[0107] No. R1No. R1

[0108] P1-1 H P1-14 OCH3

[0109] P1-2 CH3P1-15 OCHF2

[0110] P1-3 CH2F P1-16 OC2H5

[0111] P1-4 CHF2P1-17 CN

[0112] P1-5 CF3P1-18 F

[0113] P1-6 C2H5P1-19 Cl

[0114] P1-7 CH(CH3)2P1-20 Br

[0115] P1-8 CH2CH2CH3

[0116] P1-21

[0117] P1-9 CH=CH2

[0118] P1-10 CH2CH=CH2

[0119] P1-11 CHCH P1-22

[0120] P1-12 CH2CHCH

[0121]

[0122] P1-13 OCF3

[0123]

[0124] According to one embodiment of the compound of formula I, R2is in each case independently selected from H, halogen, CN, Ci-C6-alkyl, Ci-C6-halogenalkyl, O-Ci-C6-alkyl, S-Ci-C6-alkyl, O-Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl.

[0125] According to one further embodiment of the compound of formula I, R2is in each case independently selected from H, CN, halogen, Ci-C6-alkyl, Ci-C6-halogenalkyl, O-Ci-C6-alkyl, C2-C6-alkenyl, C3-C6-cycloalkyl.

[0126] According to one further embodiment of the compound of formula I, R2is in each case independently selected from H, CN, Cl, Br, CH3, C2H5, CHF2, CH2CH=CH2, cyclopropyl.

[0127] According to still another embodiment of formula I, R2is H.250444W001

[0128] According to still another embodiment of formula I, R2is halogen, in particular F, Cl, Br or I, more specifically F, Cl or Br, in particular Br or Cl.

[0129] According to still another embodiment of formula I, R2is F.

[0130] According to still another embodiment of formula I, R2is Cl.

[0131] According to still another embodiment of formula I, R2is Br.

[0132] According to still another embodiment of formula I, R2is CN.

[0133] According to still another embodiment of formula I, R2is Ci-C6-alkyl, in particular Ci-C4-alkyl, such as CH3or C2H5, in particular CH3or CH2CH3.

[0134] According to still another embodiment of formula I, R2is Ci-C6-halogenalkyl, in particular C1-C4-halogenalkyl, such as CHF2Oder CF3.

[0135] According to a further specific embodiment of formula I, R2is O-Ci-C6-alkyl, in particular O-C1-C4-alkyl, more specifically Ci-C2-alkoxy. R2is such as OCH3or OCH2CH3.

[0136] According to a further specific embodiment of formula I, R2is S-Ci-C6-alkyl, in particular S-C1-C4-alkyl, more specifically S-Ci-C2-alkyl. R2is such as SCH3or SCH2CH3.

[0137] According to still another embodiment of formula I, R2is 0-Ci-C6-halogenalkyl, in particular O-Ci-C4-halogenalkyl, such as OCF3or OCHF2.

[0138] According to still a further embodiment of formula I, R2is C2-C6-alkenyl, in particular C2-C4-alk-enyl, such as CH=CH2, C(CH3)=CH2, CH2CH=CH2.

[0139] According to still a further embodiment of formula I, R2is C2-C6-alkynyl or C2-C6-halogenalkynyl, in particular C2-C4-alkynyl or C2-C4-halogenalkynyl, such as CHCH, CH2CHCH, CHCCI, CH2CHCCI, orCCI2CHCCI.

[0140] According to still another embodiment of formula I, R2is C3-C6-cycloalkyl, in particular cyclopropyl or cyclobutyl.

[0141] Particularly preferred embodiments of R2according to the invention are in Table P2 below, wherein each line of lines P2-1 to P2-22 corresponds to one particular embodiment of the invention, wherein P2-1 to P2-22 are also in any combination with one another a preferred embodiment of the present invention. The connection point to the carbon atom, to which R2is bound is marked with

[0142]

[0143] in the drawings.

[0144] Table P2:

[0145] No. R2No. R2

[0146] P2-1 H P2-6 C2H5

[0147] P2-2 CH3P2-7 CH(CH3)2

[0148] P2-3 CH2F P2-8 CH2CH2CH3

[0149] P2-4 CHF2P2-9 CH=CH2

[0150] P2-5 CF3P2-10 CH2CH=CH2

[0151]

[0152]

[0153] 250444W001

[0154] No. R2No. R2

[0155] P2-11 CHCH P2-18 F

[0156] P2-12 CH2CHCH P2-19 Cl

[0157] P2-13 OCF3P2-20 Br

[0158] P2-14 OCH3

[0159] P2-21

[0160] P2-15 OCHF2

[0161] P2-16 OC2H5

[0162] P2-17 CN P2-22#^>

[0163]

[0164]

[0165] According to one embodiment of the compound of formula I, R3is in each case independently selected from H, halogen, CN, Ci-C6-alkyl, Ci-C6-halogenalkyl, O-Ci-C6-alkyl, S-Ci-C6-alkyl, O-Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl.

[0166] According to one further embodiment of the compound of formula I, R3is in each case independently selected from H, CN, halogen, Ci-C6-alkyl, Ci-C6-halogenalkyl, O-Ci-C6-alkyl, C2-C6-alkenyl, C3-C6-cycloalkyl.

[0167] According to one further embodiment of the compound of formula I, R3is in each case independently selected from H, CN, Cl, Br, CH3, C2H5, CHF2, CH2CH=CH2, cyclopropyl.

[0168] According to still another embodiment of formula I, R3is H.

[0169] According to still another embodiment of formula I, R3is halogen, in particular F, Cl, Br or I, more specifically F, Cl or Br, in particular Br or Cl.

[0170] According to still another embodiment of formula I, R3is F.

[0171] According to still another embodiment of formula I, R3is Cl.

[0172] According to still another embodiment of formula I, R3is Br.

[0173] According to still another embodiment of formula I, R3is CN.

[0174] According to still another embodiment of formula I, R3is Ci-C6-alkyl, in particular Ci-C4-alkyl, such as CH3or C2H5, in particular CH3or CH2CH3.

[0175] According to still another embodiment of formula I, R3is Ci-C6-halogenalkyl, in particular C1-C4-halogenalkyl, such as CHF2or CF3.

[0176] According to a further specific embodiment of formula I, R3is O-Ci-C6-alkyl, in particular O-C1-C4-alkyl, more specifically Ci-C2-alkoxy. R3is such as OCH3or OCH2CH3.

[0177] According to a further specific embodiment of formula I, R3is S-Ci-C6-alkyl, in particular S-C1-C4-alkyl, more specifically S-Ci-C2-alkyl. R3is such as SCH3or SCH2CH3.250444W001

[0178] 12

[0179] According to still another embodiment of formula I, R3is 0-Ci-C6-halogenalkyl, in particular O-Ci-C4-halogenalkyl, such as OCF3or OCHF2.

[0180] According to still a further embodiment of formula I, R3is C2-C6-alkenyl, in particular C2-C4-alk-enyl, such as CH=CH2, C(CH3)=CH2, CH2CH=CH2.

[0181] According to still a further embodiment of formula I, R3is C2-C6-alkynyl or C2-C6-halogenalkynyl, in particular C2-C4-alkynyl or C2-C4-halogenalkynyl, such as CHCH, CH2CHCH, CHCCI, CH2CHCCI, orCCI2CHCCI.

[0182] According to still another embodiment of formula I, R3is C3-C6-cycloalkyl, in particular cyclopropyl or cyclobutyl.

[0183] Particularly preferred embodiments of R3according to the invention are in Table P3 below, wherein each line of lines P3-1 to P3-22 corresponds to one particular embodiment of the invention, wherein P3-1 to P3-22 are also in any combination with one another a preferred embodiment of the present invention. The connection point to the carbon atom, to which R3is bound is marked with in the drawings.

[0184] Table P3:

[0185] No. R3No. R3

[0186] P3-1 H P3-14 OCH3

[0187] P3-2 CH3P3-15 OCHF2

[0188] P3-3 CH2F P3-16 OC2H5

[0189] P3-4 CHF2P3-17 CN

[0190] P3-5 CF3P3-18 F

[0191] P3-6 C2H5P3-19 Cl

[0192] P3-7 CH(CH3)2P3-20 Br

[0193] P3-8 CH2CH2CH3

[0194] P3-21

[0195] P3-9 CH=CH2

[0196] P3-10 CH2CH=CH2

[0197] P3-11 CHCH P3-22 <Q>

[0198] P3-12 CH2CHCH

[0199]

[0200] P3-13 OCF3

[0201]

[0202] According to one embodiment of the compound of formula I, R4is in each case independently selected from H, halogen, CN, Ci-C6-alkyl, Ci-C6-halogenalkyl, O-Ci-C6-alkyl, S-Ci-C6-alkyl, O-Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl.

[0203] According to still another embodiment of formula I, R4is H.

[0204] According to still another embodiment of formula I, R4is halogen, in particular F, Cl, Br or I,250444W001

[0205] 13

[0206] more specifically F, Cl or Br, in particular Br or Cl.

[0207] According to still another embodiment of formula I, R4is F.

[0208] According to still another embodiment of formula I, R4is Cl.

[0209] According to still another embodiment of formula I, R4is Br.

[0210] According to still another embodiment of formula I, R4is CN.

[0211] According to still another embodiment of formula I, R4is Ci-C6-alkyl, in particular Ci-C4-alkyl, such as CH3or C2H5, in particular CH3or CH2CH3.

[0212] According to still another embodiment of formula I, R4is Ci-C6-halogenalkyl, in particular C1-C4-halogenalkyl, such as CF3.

[0213] According to a further specific embodiment of formula I, R4is O-Ci-C6-alkyl, in particular O-C1-C4-alkyl, more specifically Ci-C2-alkoxy. R4is such as OCH3or OCH2CH3.

[0214] According to a further specific embodiment of formula I, R4is S-Ci-C6-alkyl, in particular S-C1-C4-alkyl, more specifically S-Ci-C2-alkyl. R4is such as SCH3or SCH2CH3.

[0215] According to still another embodiment of formula I, R4is 0-Ci-C6-halogenalkyl, in particular O-Ci-C4-halogenalkyl, such as OCF3or OCHF2.

[0216] According to still a further embodiment of formula I, R4is C2-C6-alkenyl, in particular C2-C4-alk-enyl, such as CH=CH2, C(CH3)=CH2, CH2CH=CH2.

[0217] According to still a further embodiment of formula I, R4is C2-C6-alkynyl or C2-C6-halogenalkynyl, in particular C2-C4-alkynyl or C2-C4-halogenalkynyl, such as CHCH, CH2CHCH, CHCCI, CH2CHCCI, orCCI2CHCCI.

[0218] According to still another embodiment of formula I, R4is C3-C6-cycloalkyl, in particular cyclopropyl or cyclobutyl.

[0219] Particularly preferred embodiments of R4according to the invention are in Table P4 below, wherein each line of lines P4-1 to P4-22 corresponds to one particular embodiment of the invention, wherein P4-1 to P4-22 are also in any combination with one another a preferred embodiment of the present invention. The connection point to the carbon atom, to which R4is bound is marked with in the drawings.

[0220] Table P4:

[0221] No. R4No. R4

[0222] P4-1 H P4-7 CH(CH3)2

[0223] P4-2 CH3P4-8 CH2CH2CH3

[0224] P4-3 CH2F P4-9 CH=CH2

[0225] P4-4 CHF2P4-10 CH2CH=CH2

[0226] P4-5 CF3P4-11 CHCH

[0227] P4-6 C2H5P4-12 CH2CHCH

[0228]

[0229]

[0230] 250444W001

[0231] 14

[0232] No. R4No. R4

[0233] P4-13 OCF3P4-19 Cl

[0234] P4-14 OCH3P4-20 Br

[0235] P4-15 OCHF2

[0236] P4-21

[0237] P4-16 OC2H5

[0238] P4-17 CN

[0239] P4-18 F P4-22

[0240]

[0241]

[0242] According to one embodiment of the compound of formula I, R5is in each case independently selected from hydrogen, halogen, CN, Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, phenyl or benzyl, heterocyclic aromatics and CH2-heterocyclic aromatics, wherein the aliphatic or aromatic radicals are unsubstituted or carry 1 , 2 or 3 substituents R5a; where each R5ais independently halogen, CN, Ci-C6-alkyl, C1-C6-halogenalkyl or Ci-C6-alkoxy.

[0243] According to one embodiment of the compound of formula I, R5is in each case independently selected from H (embodiment R5-1), F, CN, Ci-C6-alkyl (embodiment R5-2), Ci-C6-halogenalkyl, C2-C6-alkenyl, phenyl, benzyl, where the mentioned aliphatic or aromatic radicals are unsubstituted or carry 1 , 2 or 3 substituents R5a;

[0244] where each R5ais independently halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl or or O-Ci-C6-alkyl. According to one embodiment of the compound of formula I, R5is H, Ci-C6-alkyl or CH2-phenyl, preferably H, CH3, C2H5or CH2-phenyl.

[0245] According to a further embodiment of the compound of formula I, R5is H.

[0246] According to a further embodiment of the compound of formula I, R5is F.

[0247] According to a further embodiment of the compound of formula I, R5is CN.

[0248] According to a further embodiment of the compound of formula I, R5is Ci-C6-alkyl such as CH3, CH2CH3, CH(CH3)2, CH(CH3)CH2CH3, C(CH3)3, CH2-CH(CH3)2, CH2-C(CH3)3.

[0249] According to a further embodiment of formula I, R5is Ci-C6-halogenalkyl, in particular C1-C4-halogenalkyl, such as CHF2or CF3.

[0250] According to a further embodiment of formula I, R5is C2-C6-alkenyl, in particular C2-C4-alkenyl, such as CH=CH2, C(CH3)=CH2, CH2CH=CH2.

[0251] According to a further specific embodiment of formula I, R5is C2-C6-halogenalkenyl, in particular C2-C4-halogenalkenyl, more specifically C2-C3-halogenalkenyl such as CH=CHF, CH=CHCI, CH=CF2, CH=CCI2, CH2CH=CHF, CH2CH=CHCI, CH2CH=CF2, CH2CH=CCI2, CF2CH=CF2, CCI2CH=CCI2, CF2CF=CF2, CCI2CCI=CCI2.250444W001

[0252] 15

[0253] According to still a further embodiment of formula I, R5is C2-C6-alkynyl or C2-C6-halogenalkynyl, in particular C2-C4-alkynyl or C2-C4-halogenalkynyl, such as CHCH, CH2CHCH.

[0254] According to a further embodiment of formula I, R5is phenyl.

[0255] According to a further embodiment of formula I, R5is benzyl.

[0256] According to one further embodiment of the compound of formula I, R5is 2-F-phenyl, 4-F-phenyl, 2,4-F2-phenyl, 2-CI-phenyl, 4-CI-phenyl, CH2-phenyl, CH2-2-F-phenyl, CH2-4-F-phenyl. Particularly preferred embodiments of R5according to the invention are in Table P5 below, wherein each line of lines P5-1 to P5-22 corresponds to one particular embodiment of the invention, wherein P5-1 to P5-22 are also in any combination with one another a preferred embodiment of the present invention.

[0257] Table P5:

[0258] No. R5No. R5

[0259] P5-1 H P5-12 CH2CCH

[0260] P5-2 F P5-13 C6H5

[0261] P5-3 CH3P5-14 CH2C6H5

[0262] P5-4 C2H5P5-15 2-F-C6H5

[0263] P5-5 CH(CH3)2P5-16 4-F-C6H5

[0264] P5-6 CH2CH2CH3P5-17 2-CI-C6H5

[0265] P5-7 CHF2P5-18 4-CI-C6H5

[0266] P5-8 CH2F P5-19 2-F-CH2-C6H5

[0267] P5-9 CF3P5-20 4-F-CH2-C6H5

[0268] P5-10 CH=CH2P5-21 2-CI-CH2-C6H5

[0269] P5-11 CH2CH=CH2P5-22 4-CI-CH2-C6H5

[0270]

[0271]

[0272] According to one embodiment of the compound of formula I, R6is in each case independently selected from hydrogen, halogen, CN, Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, phenyl or benzyl, heterocyclic aromatics and CH2-heterocyclic aromatics, wherein the aliphatic or aromatic radicals are unsubstituted or carry 1 , 2 or 3 substituents R6a; where each R6ais independently halogen, CN, Ci-C6-alkyl, Ci-C6-halogenalkyl or Ci-C6-alkoxy.

[0273] According to one embodiment of the compound of formula I, R6is in each case independently selected from H (embodiment R6-1), F, CN, Ci-C6-alkyl (embodiment R6-2), Ci-C6-halogenalkyl, C2-C6-alkenyl, phenyl, benzyl, where the mentioned aliphatic or aromatic radicals are unsubstituted or carry 1 , 2 or 3 substituents R6a;

[0274] where each R6ais independently halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl or or O-Ci-C6-alkyl.250444W001

[0275] According to one embodiment of the compound of formula I, R6is H, Ci-C6-alkyl or CH2-phenyl, preferably H, CH3, C2H5or CH2-phenyl.

[0276] According to a further embodiment of the compound of formula I, R6is H.

[0277] According to a further embodiment of the compound of formula I, R6is F.

[0278] According to a further embodiment of the compound of formula I, R6is CN.

[0279] According to a further embodiment of the compound of formula I, R6is Ci-C6-alkyl such as CH3, CH2CH3, CH(CH3)2, CH(CH3)CH2CH3, C(CH3)3, CH2-CH(CH3)2, CH2-C(CH3)3.

[0280] According to a further embodiment of formula I, R6is Ci-C6-halogenalkyl, in particular C1-C4-halogenalkyl, such as CHF2or CF3.

[0281] According to a further embodiment of formula I, R6is C2-C6-alkenyl, in particular C2-C4-alkenyl, such as CH=CH2, C(CH3)=CH2, CH2CH=CH2.

[0282] According to a further specific embodiment of formula I, R6is C2-C6-halogenalkenyl, in particular C2-C4-halogenalkenyl, more specifically C2-C3-halogenalkenyl such as CH=CHF, CH=CHCI, CH=CF2, CH=CCI2, CH2CH=CHF, CH2CH=CHCI, CH2CH=CF2, CH2CH=CCI2, CF2CH=CF2, CCI2CH=CCI2, CF2CF=CF2, CCI2CCI=CCI2.

[0283] According to still a further embodiment of formula I, R6is C2-C6-alkynyl or C2-C6-halogenalkynyl, in particular C2-C4-alkynyl or C2-C4-halogenalkynyl, such as CHCH, CH2CHCH.

[0284] According to a further embodiment of formula I, R6is phenyl.

[0285] According to a further embodiment of formula I, R6is benzyl.

[0286] According to one further embodiment of the compound of formula I, R6is 2-F-phenyl, 4-F-phenyl, 2,4-F2-phenyl, 2-CI-phenyl, 4-CI-phenyl, CH2-phenyl, CH2-2-F-phenyl, CH2-4-F-phenyl. Particularly preferred embodiments of R6according to the invention are in Table P6 below, wherein each line of lines P6-1 to P6-22 corresponds to one particular embodiment of the invention, wherein P6-1 to P6-22 are also in any combination with one another a preferred embodiment of the present invention.

[0287] Table P6:

[0288] No. R6No. R6

[0289] P6-1 H P6-8 CH2F

[0290] P6-2 F P6-9 CF3

[0291] P6-3 CH3P6-10 CH=CH2

[0292] P6-4 C2H5P6-11 CH2CH=CH2

[0293] P6-5 CH(CH3)2P6-12 CH2CCH

[0294] P6-6 CH2CH2CH3P6-13 C6H5

[0295] P6-7 CHF2P6-14 CH2C6H5

[0296]

[0297]

[0298] 250444W001

[0299] No. R6No. R6

[0300] P6-15 2-F-C6H5P6-19 2-F-CH2-C6H5

[0301] P6-16 4-F-C6H5P6-20 4-F-CH2-C6H5

[0302] P6-17 2-CI-C6H5P6-21 2-CI-CH2-C6H5

[0303] P6-18 4-CI-C6H5P6-22 4-CI-CH2-C6H5

[0304]

[0305]

[0306] According to a further embodiment of the compound of formula I, R5and R6, together with the C atoms to which they are bound, form an oxo group (=0); or a thioxo group (=S); or

[0307] R5and R6, together with the carbon atom to which they are bound, form a 3-, 4-, 5- or 6-membered saturated carbocyclic ring ora 3-, 4-, 5- or 6-membered saturated heterocyclic ring containing 1, 2 or 3 heteroatoms selected from O and S as ring members; where the carbocyclic or heterocyclic ring is unsubstituted or carries 1 , 2 or 3 substituents R56;

[0308] where each R56is independently halogen, Ci-C6-alkyl or Ci-C6-halogenalkyl.

[0309] According to a further embodiment of the compound of formula I, R5and R6together with the carbon atom to which they are bound, form (=0) (embodiment R56-1).

[0310] According to a further embodiment of the compound of formula I, R5and R6together with the carbon atom to which they are bound, form (=S).

[0311] According to a further embodiment of the compound of formula I, R5and R6together with the carbon atom to which they are bound, form C3-C6-cycloalkyl (embodiment R56-2).

[0312] According to a further embodiment of the compound of formula I, R5and R6together with the carbon atom to which they are bound, form 3- to 6-membered saturated heterocycle which contains 1 , 2 or 3 heteroatoms from the group consisting of O and S.

[0313] According to a further embodiment of the compound of formula I, R5and R6together with the carbon atom to which they are bound, form 3- to 6-membered saturated heterocycle which contains one O.

[0314] Prefferred embodiments of R5, R6according to the invention are in Table P56 below, wherein each line of lines P56-1 to P56-20 corresponds to one particular embodiment of the invention, wherein P56-1 to P56-20 are also in any combination with one another a preferred embodiment of the present invention. The connection point to the carbon atom, to which R5and R6is bound is marked with in the drawings.

[0315] Table P56:

[0316] No. R5R6No. R5R6

[0317] P56-1 =0

[0318] P56-3 #

[0319] P56-2 =s

[0320]

[0321]

[0322] 250444W001

[0323] No. R5R6No. R5R6

[0324] P56-4 # P56-13 #4^

[0325] #

[0326] P56-5 °— .

[0327] # P56-14

[0328] #

[0329] P56-6 #42^

[0330] #

[0331] P56-15

[0332] o #

[0333] #—

[0334] P56-7

[0335] # 1-0

[0336] 0 P56-16

[0337] P56-8 #

[0338] #

[0339] °— |

[0340] P56-9 #—) —

[0341] # P56-17

[0342] i-°

[0343] P56-10 #—) — '

[0344] # ox''>

[0345] P56-18

[0346] #

[0347] P56-11 o

[0348] a P56-19

[0349] #

[0350] P56-12

[0351] a / r^o

[0352]

[0353] P56-20

[0354] #

[0355]

[0356] According to one embodiment of the compound of formula I, R7is in each case independently selected from hydrogen, halogen, CN, Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, phenyl or benzyl, heterocyclic aromatics and CH2-heterocyclic aromatics, wherein the aliphatic or aromatic radicals are unsubstituted or carry 1 , 2 or 3 substituents R7a; where each R7ais independently halogen, CN, Ci-C6-alkyl, Ci-C6-halogenalkyl or Ci-C6-alkoxy.

[0357] According to one embodiment of the compound of formula I, R7is in each case independently selected from H (embodiment R7-1), F, CN, Ci-C6-alkyl (embodiment R7-2), Ci-C6-halogenalkyl, C2-C6-alkenyl, phenyl, benzyl, where the mentioned aliphatic or aromatic radicals are unsubstituted or carry 1 , 2 or 3 substituents R7a;

[0358] where each R7ais independently halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl or or O-Ci-C6-alkyl. According to one embodiment of the compound of formula I, R7is H, Ci-C6-alkyl or CH2-phenyl, preferably H, CH3, C2H5or CH2-phenyl.250444W001

[0359] According to a further embodiment of the compound of formula I, R7is H.

[0360] According to a further embodiment of the compound of formula I, R7is F.

[0361] According to a further embodiment of the compound of formula I, R7is CN.

[0362] According to a further embodiment of the compound of formula I, R7is Ci-C6-alkyl such as CH3, CH2CH3, CH(CH3)2, CH(CH3)CH2CH3, C(CH3)3, CH2-CH(CH3)2, CH2-C(CH3)3.

[0363] According to a further embodiment of formula I, R7is Ci-C6-halogenalkyl, in particular C1-C4-halogenalkyl, such as CHF2or CF3.

[0364] According to a further embodiment of formula I, R7is C2-C6-alkenyl, in particular C2-C4-alkenyl, such as CH=CH2, C(CH3)=CH2, CH2CH=CH2.

[0365] According to a further specific embodiment of formula I, R7is C2-C6-halogenalkenyl, in particular C2-C4-halogenalkenyl, more specifically C2-C3-halogenalkenyl such as CH=CHF, CH=CHCI, CH=CF2, CH=CCI2, CH2CH=CHF, CH2CH=CHCI, CH2CH=CF2, CH2CH=CCI2, CF2CH=CF2, CCI2CH=CCI2, CF2CF=CF2, CCI2CCI=CCI2.

[0366] According to still a further embodiment of formula I, R7is C2-C6-alkynyl or C2-C6-halogenalkynyl, in particular C2-C4-alkynyl or C2-C4-halogenalkynyl, such as CHCH, CH2CHCH.

[0367] According to a further embodiment of formula I, R7is phenyl.

[0368] According to a further embodiment of formula I, R7is benzyl.

[0369] According to one further embodiment of the compound of formula I, R7is 2-F-phenyl, 4-F-phenyl, 2,4-F2-phenyl, 2-CI-phenyl, 4-CI-phenyl, CH2-phenyl, CH2-2-F-phenyl, CH2-4-F-phenyl. Particularly preferred embodiments of R7according to the invention are in Table P7 below, wherein each line of lines P7-1 to P7-22 corresponds to one particular embodiment of the invention, wherein P7-1 to P7-22 are also in any combination with one another a preferred embodiment of the present invention.

[0370] Table P7:

[0371] No. R7No. R7

[0372] P7-1 H P7-10 CH=CH2

[0373] P7-2 F P7-11 CH2CH=CH2

[0374] P7-3 CH3P7-12 CH2CCH

[0375] P7-4 C2H5P7-13 C6H5

[0376] P7-5 CH(CH3)2P7-14 CH2C6H5

[0377] P7-6 CH2CH2CH3P7-15 2-F-C6H5

[0378] P7-7 CHF2P7-16 4-F-C6H5

[0379] P7-8 CH2F P7-17 2-CI-C6H5

[0380] P7-9 CF3P7-18 4-CI-C6H5

[0381]

[0382]

[0383] 250444W001

[0384] 20

[0385] No. R7No. R7

[0386] P7-19 2-F-CH2-C6H5P7-21 2-CI-CH2-C6H5

[0387] P7-20 4-F-CH2-C6H5P7-22 4-CI-CH2-C6H5

[0388]

[0389]

[0390] According to one embodiment of the compound of formula I, R8is in each case independently selected from hydrogen, halogen, CN, Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, phenyl or benzyl, heterocyclic aromatics and CH2-heterocyclic aromatics, wherein the aliphatic or aromatic radicals are unsubstituted or carry 1 , 2 or 3 substituents R8a; where each R8ais independently halogen, CN, Ci-C6-alkyl, Ci-C6-halogenalkyl or Ci-C6-alkoxy.

[0391] According to one embodiment of the compound of formula I, R8is in each case independently selected from H (embodiment R8-1), F, CN, Ci-C6-alkyl (embodiment R8-2), Ci-C6-halogenalkyl, C2-C6-alkenyl, phenyl, benzyl, where the mentioned aliphatic or aromatic radicals are unsubstituted or carry 1 , 2 or 3 substituents R8a;

[0392] where each R8ais independently halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl or or O-Ci-C6-alkyl. According to one embodiment of the compound of formula I, R8is H, Ci-C6-alkyl or CH2-phenyl, preferably H, CH3, C2H5or CH2-phenyl.

[0393] According to a further embodiment of the compound of formula I, R8is H.

[0394] According to a further embodiment of the compound of formula I, R8is F.

[0395] According to a further embodiment of the compound of formula I, R8is CN.

[0396] According to a further embodiment of the compound of formula I, R8is Ci-C6-alkyl such as CH3, CH2CH3, CH(CH3)2, CH(CH3)CH2CH3, C(CH3)3, CH2-CH(CH3)2, CH2-C(CH3)3.

[0397] According to a further embodiment of formula I, R8is Ci-C6-halogenalkyl, in particular C1-C4-halogenalkyl, such as CHF2or CF3.

[0398] According to a further specific embodiment of formula I, R8is C2-C6-halogenalkenyl, in particular C2-C4-halogenalkenyl, more specifically C2-C3-halogenalkenyl such as CH=CHF, CH=CHCI, CH=CF2, CH=CCI2, CH2CH=CHF, CH2CH=CHCI, CH2CH=CF2, CH2CH=CCI2, CF2CH=CF2, CCI2CH=CCI2, CF2CF=CF2, CCI2CCI=CCI2.

[0399] According to still a further embodiment of formula I, R8is C2-C6-alkynyl or C2-C6-halogenalkynyl, in particular C2-C4-alkynyl or C2-C4-halogenalkynyl, such as CHCH, CH2CHCH.

[0400] According to a further embodiment of formula I, R8is phenyl.

[0401] According to a further embodiment of formula I, R8is benzyl.

[0402] According to one further embodiment of the compound of formula I, R8is 2-F-phenyl, 4-F-phenyl, 2,4-F2-phenyl, 2-CI-phenyl, 4-CI-phenyl, CH2-phenyl, CH2-2-F-phenyl, CH2-4-F-phenyl. Particularly preferred embodiments of R8according to the invention are in Table P8 below, wherein each line of lines P8-1 to P8-22 corresponds to one particular embodiment of the invention, wherein P8-1 to P8-22 are also in any combination with one another a preferred250444W001

[0403] embodiment of the present invention.

[0404] Table P8:

[0405] No. R8No. R8

[0406] P8-1 H P8-12 CH2CCH

[0407] P8-2 F P8-13 C6H5

[0408] P8-3 CH3P8-14 CH2C6H5

[0409] P8-4 C2H5P8-15 2-F-C6H5

[0410] P8-5 CH(CH3)2 P8-16 4-F-C6H5

[0411] P8-6 CH2CH2CH3P8-17 2-CI-C6H5

[0412] P8-7 CHF2P8-18 4-CI-C6H5

[0413] P8-8 CH2F P8-19 2-F-CH2-C6H5

[0414] P8-9 CF3P8-20 4-F-CH2-C6H5

[0415] P8-10 CH=CH2P8-21 2-CI-CH2-C6H5

[0416] P8-11 CH2CH=CH2P8-22 4-CI-CH2-C6H5

[0417]

[0418]

[0419] According to a further embodiment of the compound of formula I, R7and R8, together with the C atoms to which they are bound, form an oxo group (=0); or a thioxo group (=S); or

[0420] R7and R8, together with the carbon atom to which they are bound, form a 3-, 4-, 5- or 6-membered saturated carbocyclic ring ora 3-, 4-, 5- or 6-membered saturated heterocyclic ring containing 1, 2 or 3 heteroatoms selected from O and S as ring members; where the carbocyclic or heterocyclic ring is unsubstituted or carries 1 , 2 or 3 substituents R78;

[0421] where each R78is independently halogen, Ci-C6-alkyl or Ci-C6-halogenalkyl.

[0422] According to a further embodiment of the compound of formula I, R7and R8together with the carbon atom to which they are bound, form (=0) (embodiment R78-1).

[0423] According to a further embodiment of the compound of formula I, R7and R8together with the carbon atom to which they are bound, form (=S).

[0424] According to a further embodiment of the compound of formula I, R7and R8together with the carbon atom to which they are bound, form C3-C6-cycloalkyl (embodiment R78-2).

[0425] According to a further embodiment of the compound of formula I, R7and R8together with the carbon atom to which they are bound, form 3- to 6-membered saturated heterocycle which contains 1 , 2 or 3 heteroatoms from the group consisting of O and S.

[0426] According to a further embodiment of the compound of formula I, R7and R8together with the carbon atom to which they are bound, form 3- to 6-membered saturated heterocycle which contains one O.250444W001

[0427] 22

[0428] Prefferred embodiments of R7, R8according to the invention are in Table P78 below, wherein each line of lines P78-1 to P78-20 corresponds to one particular embodiment of the invention, wherein P78-1 to P78-20 are also in any combination with one another a preferred embodiment of the present invention. The connection point to the carbon atom, to which R7and R8is bound is marked with in the drawings.

[0429] Table P78:

[0430] No. R7R8No. R7R8

[0431] P78-1 =0

[0432] P78-12 #- P78-2 =s a /

[0433] #— — /

[0434] P78-3 # P78-13

[0435] #

[0436] P78-4 # o— .

[0437] P78-14

[0438] #

[0439] P78-5#- / 3^

[0440] #

[0441] P78-15

[0442] #

[0443] P78-6

[0444] #

[0445] i-O

[0446] o

[0447] #— P78-16

[0448] P78-7

[0449] # #

[0450] 0

[0451] P78-8

[0452] # P78-17

[0453] °— ]

[0454] P78-9 #—] —

[0455] #

[0456] P78-18

[0457] i-° #

[0458] P78-10 — i

[0459] # o

[0460] P78-19

[0461] #

[0462] P78-11

[0463] a r^o

[0464]

[0465] P78-20

[0466] #

[0467]

[0468] According to one further embodiment of the compound of formula I, R9is in each case independently selected from H, CN, CH2CN, CH(CH3)CN, CH(=O), -C(=O)Ci-C6-alkyl, -C(=O)C2-C6-alkenyl, -C(=O)C2-C6-alkynyl, -C(=0)C3-C6-cycloalkyl, -C(=O)-N(H)Ci-C4-alkyl, -C(=O)-N(Ci-C4-alkyl)2, Ci-C6-alkyl, Ci-C6-alkoxy, Ci-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-250444W001

[0469] 23

[0470] halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, -S(=O)2-R9a, five- or six-membered heteroaryl, aryl or benzyl; wherein heteroaryl contains 1 , 2 or 3 heteroatoms selected from N, O and S as ring members; wherein aryl and the phenyl ring in benzyl are unsubstituted or carry 1 , 2, 3, 4 or 5 substituents selected from the group consisting of CN, halogen, OH, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy; wherein the phenyl ring in benzyl is unsubstituted or carries 1 , 2 or 3 substituents selected from the group consisting of CN and halogen; wherein

[0471] R9ais Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl or benzyl, where the phenyl ring in the two last- mentioned radicals is unsubstituted or carries 1 , 2 or 3 substituents each independently selected from the group consisting of halogen, Ci-C6-alkyl, Ci- C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl and C2-C6- haloalkynyl.

[0472] According to a further embodiment of formula I, R9is in each case independently selected from CN, Ci-C6-alkyl, C2-C6-alkenyl or C2-C6-alkynyl.

[0473] According to a further embodiment of formula I, R9is in each case independently selected from CN, CH3, CH2CH=CH2or CH2CCH.

[0474] According to a further embodiment of formula I, R9is H.

[0475] According to a further embodiment of formula I, R9is Cl, F.

[0476] According to a further embodiment of formula I, R9is CN, CH2CN or CH(CH3)CN.

[0477] According to a further specific embodiment of formula I, R9is CH(=O).

[0478] According to a further specific embodiment of formula I, R9is OCH3or OCH2CH3.

[0479] According to a further specific embodiment of formula I, R9is C(=O)Ci-C6-alkyl, wherein alkyl is CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.

[0480] According to a further specific embodiment of formula I, R9is C(=O)C2-C6-alkenyl, wherein alkenyl is CH=CH2, CH2CH=CH2.

[0481] According to a further specific embodiment of formula I, R9is C(=O)C2-C6-alkynyl, wherein alkynyl is CHCH, CH2CHCH.

[0482] According to a further specific embodiment of formula I, R9is C(=0)C3-C6-cycloalkyl, wherein cycloalkyl is cyclopropyl (C3H7) or cyclobutyl (C4H9).

[0483] According to a further specific embodiment of formula I, R9is C(=O)NH-Ci-C4-alkyl or C(=O)N-(Ci-C4-alkyl)2, wherein alkyl is CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, According to a further embodiment of formula I, R9is Ci-C6-alkyl, such as CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.

[0484] According to a further embodiment of formula I, R9is Ci-C6-alkyl, in particular Ci-C4-alkyl, such250444W001

[0485] 24

[0486] as CH3, C2H5, n-propyl, i-propyl.

[0487] According to a further embodiment of formula I, R9is Ci-C6-halogenalkyl, in particular C1-C4-halogenalkyl, such as CF3, CCI3, FCH2, CICH2, F2CH, CI2CH, CF3CH2, CCI3CH2orCF2CHF2. According to a further embodiment of formula I R9is C3-C6-cycloalkyl, in particular cyclopropyl. According to a further embodiment of formula I, R9is C3-C6-halogencycloalkyl. In a special embodiment R9bis fully or partially halogenated cyclopropyl, such as 1-F-cyclopropyl, 1-CI-cyclopropyl, 1 ,1-F2-cyclopropyl, 1 ,1-CI2-cyclopropyl .

[0488] According to a further embodiment of formula I, R9is C2-C6-alkenyl, in particular C2-C4-alkenyl, such as CH=CH2, C(CH3)=CH2, CH2CH=CH2, preferred CH2CH=CH2.

[0489] According to a further specific embodiment of formula I, R9is C2-C6-halogenalkenyl, in particular C2-C4-halogenalkenyl, more specifically C2-C3-halogenalkenyl such as CH=CHF, CH=CHCI, CH=CF2, CH=CCI2, CH2CH=CHF, CH2CH=CHCI, CH2CH=CF2, CH2CH=CCI2, CF2CH=CF2, CCI2CH=CCI2, CF2CF=CF2, CCI2CCI=CCI2.

[0490] According to still a further embodiment of formula I, R9is C2-C6-alkynyl or C2-C6-halogenalkynyl, in particular C2-C4-alkynyl or C2-C4-halogenalkynyl, such as CHCH, CH2CHCH, preferred CH2CHCH.

[0491] According to still a further embodiment of formula I, R9is -S(=O)2-R9a, wherein R9ais preferably Ci-C6-alkyl, in particular Ci-C4-alkyl, such as CH3, C2H5, n-propyl, i-propyl.

[0492] According to still another embodiment of formula I, R9is aryl, in particular phenyl, wherein the aryl or phenyl moiety in each case is unsubstituted or substituted by identical or different groups R9bwhich independently of one another are selected from halogen, Ci-C2-alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl and Ci-C2-halogenalkoxy, in particular F, Cl, Br, CH3, OCH3, CF3and OCF3. According to one embodiment, R9is unsubstituted phenyl. According to another embodiment, R9is phenyl, that is substituted by one, two or three, in particular one, halogen, in particular selected from F, Cl and Br, more specifically selected from F and Cl.

[0493] According to still another embodiment of formula I, R9is 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.

[0494] According to still another embodiment of formula I, R9is 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,250444W001

[0495] 25

[0496] pyrimidin-5-yl, pyrazin-2-yl and 1 ,3,5-triazin-2-yl and 1 ,2,4-triazin-3-yl.

[0497] According to still another embodiment of formula I, R9is in each case independently selected from H, halogen, OH, CN, Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy and C3-C6-cycloalkyl wherein the acyclic moieties of R9are unsubstituted or substituted with identical or different groups R9aas defined and preferably defined herein, and wherein the carbocyclic, phenyl and heteroaryl moieties of R9are unsubstituted or substituted with identical or different groups R9bas defined and preferably defined herein.

[0498] Particularly preferred embodiments of R9according to the invention are in Table P9 below, wherein each line of lines P9-1 to P9-32 corresponds to one particular embodiment of the invention, wherein P9-1 to P9-32 are also in any combination with one another a preferred embodiment of the present invention. The connection point to the carbon atom, to which R9is bound is marked with

[0499]

[0500] in the drawings.

[0501] Table P9:

[0502] No. R9No. R9

[0503] P9-1 H P9-17 CH2CHCH

[0504] P9-2 CH3P9-18 CH2CH2CH(CH3)2P9-3 CH2F P9-19 CN

[0505] P9-4 CHF2P9-20 CH2CN

[0506] P9-5 CF3P9-21 CH(CH3)CN

[0507] P9-6 C2H5P9-22 CH(=O)

[0508] P9-7 C3H7P9-23 C(=O)CH3

[0509] P9-8 CH(CH3)2P9-24 C(=O)NH-CH3

[0510] P9-9 CH2CH2CH3P9-25 C(=O)N(CH3)2

[0511] P9-10 CH2CH2CH2CH3P9-26 S(=O)2-CH3

[0512] P9-11 CH2CH(CH3)2

[0513] P9-27 #— <3

[0514] P9-12 C(CH3)3

[0515] P9-13 CH2CH2CH2CH2CH3

[0516] P9-28

[0517] P9-14 CH=CH2

[0518] P9-15 CH2CH=CH2

[0519] P9-29

[0520] P9-16 CHCH

[0521]

[0522]

[0523] 250444W001

[0524]

[0525]

[0526] According to one embodiment of the compound of formula I, X1is in each case independently selected from H (embodiment X1-1), halogen (embodiment X1-2), CN, Ci-C6-alkyl (embodiment X1-3), Ci-C6-halogenalkyl, O-Ci-C6-alkyl (embodiment X1-4), S-Ci-C6-alkyl O-Ci-C6-alkyl (embodiment X1-5), 0-Ci-C6-halogenalkyl O-Ci-C6-alkyl (embodiment X1-6), C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, phenyl, benzyl, O-phenyl, O-benzyl.

[0527] According to one embodiment of the compound of formula I, X1is in each case independently selected from H, halogen, Ci-C6-alkyl, 0-Ci-C6-halogenalkyl or S-Ci-C6-alkyl.

[0528] According to one embodiment of the compound of formula I, X1is in each case independently selected from H, Cl, F, CH3, O-CH3or S-CH3

[0529] According to one embodiment of the compound of formula I, X1is H.

[0530] According to a further embodiment of formula I, X1is halogen, in particular F, Cl, Br or I, more specifically F, Cl or Br, in particular Br or Cl.

[0531] According to still another embodiment of formula I, X1is F.

[0532] According to still another embodiment of formula I, X1is Cl.

[0533] According to still another embodiment of formula I, X1is Br.

[0534] According to still another embodiment of formula I, X1is CN.

[0535] According to a further embodiment of formula I, X1is Ci-C6-alkyl, in particular Ci-C4-alkyl, such as CH3or C2H5, in particular CH3.

[0536] According to a further embodiment of formula I, X1is Ci-C6-halogenalkyl, in particular C1-C4-halogenalkyl, such as CHF2or CF3.

[0537] According to a further embodiment of formula I, X1is O-Ci-C6-alkyl, in particular O-Ci-C4-alkyl, more specifically O-Ci-C2-alkyl. R3is such as OCH3or OCH2CH3.

[0538] According to a further embodiment of formula I, X1is S-Ci-C6-alkyl, in particular S-Ci-C4-alkyl, more specifically S-Ci-C2-alkyl. R3is such as SCH3or SCH2CH3.

[0539] According to a further embodiment of formula I, X1is 0-Ci-C6-halogenalkyl, in particular O-C1-C4-halogenalkyl, such as OCHF2or OCF3.

[0540] According to a further embodiment of formula I, X1is C2-C6-alkenyl, in particular C2-C4-alkenyl, such as CH=CH2, C(CH3)=CH2, CH2CH=CH2.

[0541] According to a further embodiment of formula I, X1is C2-C6-alkynyl, in particular C2-C4-alkynyl,250444W001

[0542] 27

[0543] such as CHCH, CH2CHCH.

[0544] According to a further embodiment of formula I, X1is C3-C6-cycloalkyl, in particular cyclopropyl or cyclo butyl.

[0545] According to a further embodiment of formula I, X1is phenyl.

[0546] According to a further embodiment of formula I, X1is O-phenyl.

[0547] According to a further embodiment of formula I, X1is benzyl.

[0548] According to a further embodiment of formula I, X1is O-benzyl.

[0549] Particularly preferred embodiments of X1according to the invention are in Table X1 below, wherein each line of lines X1-1 to X1-32 corresponds to one particular embodiment of the invention, wherein X1-1 to X1-32 are also in any combination with one another a preferred embodiment of the present invention.

[0550] Table X1:

[0551] No. X1No. X1

[0552] RX1-1 H RX1-17 SC2H5

[0553] RX1-2 Cl RX1-18 SCH(CH3)2

[0554] RX1-3 Br RX1-19 SCH2CH2CH3

[0555] RX1-4 F RX1-20 OCHF2

[0556] RX1-5 CH3RX1-21 OCH2F

[0557] RX1-6 C2H5RX1-22 OCF3

[0558] RX1-7 CH(CH3)2RX1-23 CH=CH2

[0559] RX1-8 CH2CH2CH3RX1-24 CH2CH=CH2

[0560] RX1-9 CHF2RX1-25 CHCH

[0561] RX1-10 CH2F RX1-26 CH2CHCH

[0562] RX1-11 CF3RX1-27 C3H5

[0563] RX1-12 OCH3RX1-28 C4H7

[0564] RX1-13 OC2H5RX1-29 C6H5

[0565] RX1-14 OCH(CH3)2RX1-30 CH2C6H5

[0566] RX1-15 OCH2CH2CH3RX1-31 OC6H5

[0567] RX1-16 SCH3RX1-32 OCH2C6H5

[0568]

[0569]

[0570] According to one embodiment of the compound of formula I, X2is in each case independently selected from H (embodiment X2-1), halogen (embodiment X2-2), CN, Ci-C6-alkyl (embodiment X2-3), Ci-C6-halogenalkyl, O-Ci-C6-alkyl (embodiment X2-4), S-Ci-C6-alkyl, O-Ci-C6-alkyl250444W001

[0571] 28

[0572] (embodiment X2-5), 0-Ci-C6-halogenalkyl O-Ci-C6-alkyl (embodiment X2-6), C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, phenyl, benzyl, O-phenyl, O-benzyl.

[0573] According to one embodiment of the compound of formula I, X2is in each case independently selected from H, halogen, Ci-C6-alkyl, 0-Ci-C6-halogenalkyl or S-Ci-C6-alkyl.

[0574] According to one embodiment of the compound of formula I, X2is in each case independently selected from H, Cl, F, CH3, O-CH3or S-CH3

[0575] According to one embodiment of the compound of formula I, X2is H.

[0576] According to a further embodiment of formula I, X2is halogen, in particular F, Cl, Br or I, more specifically F, Cl or Br, in particular Br or Cl.

[0577] According to still another embodiment of formula I, X2is F.

[0578] According to still another embodiment of formula I, X2is Cl.

[0579] According to still another embodiment of formula I, X2is Br.

[0580] According to still another embodiment of formula I, X2is CN.

[0581] According to a further embodiment of formula I, X2is Ci-C6-alkyl, in particular Ci-C4-alkyl, such as CH3or C2H5, in particular CH3.

[0582] According to a further embodiment of formula I, X2is Ci-C6-halogenalkyl, in particular C1-C4-halogenalkyl, such as CHF2or CF3.

[0583] According to a further embodiment of formula I, X2is O-Ci-C6-alkyl, in particular O-Ci-C4-alkyl, more specifically O-Ci-C2-alkyl. R3is such as OCH3or OCH2CH3.

[0584] According to a further embodiment of formula I, X2is S-Ci-C6-alkyl, in particular S-Ci-C4-alkyl, more specifically S-Ci-C2-alkyl. R3is such as SCH3or SCH2CH3.

[0585] According to a further embodiment of formula I, X2is 0-Ci-C6-halogenalkyl, in particular O-C1-C4-halogenalkyl, such as OCHF2or OCF3.

[0586] According to a further embodiment of formula I, X2is C2-C6-alkenyl, in particular C2-C4-alkenyl, such as CH=CH2, C(CH3)=CH2, CH2CH=CH2.

[0587] According to a further embodiment of formula I, X2is C2-C6-alkynyl, in particular C2-C4-alkynyl, such as CHCH, CH2CHCH.

[0588] According to a further embodiment of formula I, X2is C3-C6-cycloalkyl, in particular cyclopropyl or cyclo butyl.

[0589] According to a further embodiment of formula I, X2is phenyl.

[0590] According to a further embodiment of formula I, X2is O-phenyl.

[0591] According to a further embodiment of formula I, X2is benzyl.

[0592] According to a further embodiment of formula I, X2is O-benzyl.

[0593] Particularly preferred embodiments of X2according to the invention are in Table X2 below, wherein each line of lines X2-1 to X2-32 corresponds to one particular embodiment of the invention, wherein X2-1 to X2-32 are also in any combination with one another a preferred250444W001

[0594] 29

[0595] embodiment of the present invention.

[0596] Table X2:

[0597] No. X2No. X2X2-1 H X2-29 C6H5X2-2 Cl X2-30 CH2C6H5X2-3 Br X2-31 OC6H5X2-4 F X2-32 OCH2C6H5

[0598]

[0599] X2-5 CH3

[0600] X2-6 C2H5

[0601] X2-7 CH(CH3)2

[0602] X2-8 CH2CH2CH3

[0603] X2-9 CHF2

[0604] X2-10 CH2F

[0605] X2-11 CF3

[0606] X2-12 OCH3

[0607] X2-13 OC2H5

[0608] X2-14 OCH(CH3)2

[0609] X2-15 OCH2CH2CH3

[0610] X2-16 SCH3

[0611] X2-17 SC2H5

[0612] X2-18 SCH(CH3)2

[0613] X2-19 SCH2CH2CH3

[0614] X2-20 OCHF2

[0615] X2-21 OCH2F

[0616] X2-22 OCF3

[0617] X2-23 CH=CH2

[0618] X2-24 CH2CH=CH2

[0619] X2-25 CHCH

[0620] X2-26 CH2CHCH

[0621] X2-27 C3H5

[0622] X2-28 C4H7

[0623]

[0624] 250444W001

[0625] 30

[0626] The compounds of the formula I comprise one or more chiral center and are generally obtained in the form of a racemate and I or a diasteromeric mixture. The stereoisomers can be separated and isolated in pure form with methods known by the skilled person, e.g. by using chiral HPLC.

[0627] Therefore, according to the present invention, the compound of the formula I having one chiral center can be used in form of

[0628] - a racemic mixture of the of the (R)-enantiomer and the (S)-enantiomer;

[0629] - a mixture with any other proportions of the (R)-enantiomer and the (S)-enantiomer; - pure (R)-enantiomer or

[0630] - pure (S)-enantiomer.

[0631] According to one specific embodiment, the compound of the formula I is provided and used as (R)-enantiomer with an enantiomeric excess (e.e.) of at least 40%, for example, at least 50%, 60%, 70% or 80%, preferably at least 90%, more preferably at least 95%, yet more preferably at least 98% and most preferably at least 99%.

[0632] According to one specific embodiment, the compound of the formula I is provided and used as (S)-enantiomer with an enantiomeric excess (e.e.) of at least 40%, for example, at least 50%, 60%, 70% or 80%, preferably at least 90%, more preferably at least 95%, yet more preferably at least 98% and most preferably at least 99%.

[0633] Therefore, according to the present invention, the compound of the formula I having two chiral centers can be used in form of

[0634] - a racemic mixture of the of the (R,R)-enantiomer and the (S,S)-enantiomer,

[0635] - a mixture with any other proportions of the (R,R)-enantiomer and the (S,S)-enantiomer; - pure (R,R)-enantiomer or

[0636] - pure (S,S)-enantiomer.

[0637] According to one specific embodiment, the compound of the formula I is provided and used as (R,R)-enantiomer with an enantiomeric excess (e.e.) of at least 40%, for example, at least 50%, 60%, 70% or 80%, preferably at least 90%, more preferably at least 95%, yet more preferably at least 98% and most preferably at least 99%.

[0638] According to one specific embodiment, the compound of the formula I is provided and used as (S,S)-enantiomer with an enantiomeric excess (e.e.) of at least 40%, for example, at least 50%, 60%, 70% or 80%, preferably at least 90%, more preferably at least 95%, yet more preferably at least 98% and most preferably at least 99%.

[0639] Therefore, according to the present invention, the compound of the formula I having two chiral centers can be used in form of

[0640] - a racemic mixture of the of the (R,S)-enantiomer and the (S,R)-enantiomer,250444W001

[0641] 31

[0642] - a mixture with any other proportions of the (R.S)-enantiomer and the (S, R)-enantiomer; - pure (R.S)-enantiomer or

[0643] - pure (S,R)-enantiomer.

[0644] According to one specific embodiment, the compound of the formula I is provided and used as (R.S)-enantiomer with an enantiomeric excess (e.e.) of at least 40%, for example, at least 50%, 60%, 70% or 80%, preferably at least 90%, more preferably at least 95%, yet more preferably at least 98% and most preferably at least 99%.

[0645] According to one specific embodiment, the compound of the formula I is provided and used as (S,R)-enantiomer with an enantiomeric excess (e.e.) of at least 40%, for example, at least 50%, 60%, 70% or 80%, preferably at least 90%, more preferably at least 95%, yet more preferably at least 98% and most preferably at least 99%.

[0646] Therefore, according to the present invention, the compound of the formula I having two chiral centers can be used in form of

[0647] a mixture with any proportions of the (R,S)-diastereoisomer and the (S,S)-diastereoisomer According to one specific embodiment, the compound of the formula I is provided and used as (R,S)-diastereoisomer with an diastereomeric excess (d.e.) of at least 40%, for example, at least 50%, 60%, 70% or 80%, preferably at least 90%, more preferably at least 95%, yet more preferably at least 98% and most preferably at least 99%.

[0648] According to one specific embodiment, the compound of the formula I is provided and used as (S,S)-diastereoisomer with an diastereomeric excess (d.e.) of at least 40%, for example, at least 50%, 60%, 70% or 80%, preferably at least 90%, more preferably at least 95%, yet more preferably at least 98% and most preferably at least 99%.

[0649] This applies to the mixtures with any other proportions of a mixture A (composed by any proportion of (R,R)-enantiomer and the (S,S)-enantiomer) and a mixture B (composed by any proportion of (R,S)-enantiomer and the (S,R)-enantiomer).

[0650] In particular with a view to their use, according to one embodiment, preference is given to the compounds of the compounds LA-1, 1.A-2, I.A-3, I.A-4, that are compiled in the Tables 1a to 6a. Each of the groups mentioned for a substituent in the tables is furthermore per se, independently of the combination in which it is mentioned, a particularly preferred aspect of the substituent in question.250444W001

[0651]

[0652] Table 1a Compounds of the formula LA-1, I.A-2, I.A-3, I.A-4, in which R2or R3is H and the meaning of the combination of X1, X2, R5, R6, R7and R8for each individual compound corresponds in each case to one line of Table B (compounds LA-1.1a. B-1 to I.A-1.1a.B-1089, LA-2.1a. B-1 to LA-2.1a. B-1089, I.A-3.1a.B-1 to I.A-3.1a.B-1089, I.A-4.1a.B-1 to I.A-4.1a.B-1089).

[0653] Table 2a Compounds of the formula LA-1 , LA-2, LA-3, LA-4, in which R2or R3is CH3and the meaning of the combination of X1, X2, R5, R6, R7and R8for each individual compound corresponds in each case to one line of Table B (compounds LA-1.2a. B-1 to LA-1.2a. B-1089, LA-2.2a. B-1 to I.A-2.2a.B-1089, I.A-3.2a.B-1 to I.A-3.2a.B-1089, I.A-4.2a.B-1 to I.A-4.2a.B-1089).

[0654] Table 3a Compounds of the formula LA-1, LA-2, LA-3, LA-4, in which R2or R3is Cl and the meaning of the combination of X1, X2, R5, R6, R7and R8for each individual compound corresponds in each case to one line of Table B (compounds LA-1.3a. B-1 to LA-1.3a. B-1089, LA-2.3a. B-1 to LA-2.3a. B-1089, I.A-3.3a.B-1 to LA-3.3a. B-1089, I.A-4.3a.B-1 to I.A-4.3a.B-1089).

[0655] Table 4a Compounds of the formula LA-1, LA-2, LA-3, LA-4, in which R2or R3is Br and the meaning of the combination of X1, X2, R5, R6, R7and R8for each individual compound corresponds in each case to one line of Table B (compounds LA-1.4a. B-1 to LA-1.4a. B-1089, LA-2.4a. B-1 to I.A-2.4a.B-1089, I.A-3.4a.B-1 to I.A-3.4a.B-1089, I.A-4.4a.B-1 to I.A-4.4a.B-1089).

[0656] Table 5a Compounds of the formula LA-1, LA-2, LA-3, LA-4, in which R2or R3is CN and the meaning of the combination of X1, X2, R5, R6, R7and R8for each individual compound corresponds in each case to one line of Table B (compounds LA-1.5a. B-1 to LA-1.5a. B-1089, LA-250444W001

[0657] 33

[0658] No. X1X2R5R6R7R8B-1 H H H H H H B-2 H H H CH3H H B-3 H H H C2H5H H B-4 H H H CH2C6H5H H B-5 H H CH3CH3H H B-6 H H CH3C2H5H H B-7 H H CH3CH2C6H5H H B-8 H H C2H5C2H5H H B-9 H H C2H5CH2C6H5H H B-10 H H CH2C6H5CH2C6H5H H B-11 H H -CH2-CH2- H H B-12 H H H H H CH3B-13 H H H CH3H CH3B-14 H H H C2H5H CH3B-15 H H H CH2C6H5H CH3B-16 H H CH3CH3H CH3B-17 H H CH3C2H5H CH3B-18 H H CH3CH2C6H5H CH3B-19 H H C2H5C2H5H CH3B-20 H H C2H5CH2C6H5H CH3B-21 H H CH2C6H5CH2C6H5H CH3B-22 H H -CH2-CH2- H CH3B-23 H H H H H C2H5B-24 H H H CH3H C2H5B-25 H H H C2H5H C2H5B-26 H H H CH2C6H5H C2H5B-27 H H CH3CH3H C2H5

[0659]

[0660] 250444W001

[0661] 34

[0662] No. X1X2R5R6R7R8B-28 H H CH3C2H5H C2H5B-29 H H CH3CH2C6H5H C2H5B-30 H H C2H5C2H5H C2H5B-31 H H C2H5CH2C6H5H C2H5B-32 H H CH2C6H5CH2C6H5H C2H5B-33 H H -CH2-CH2- H C2H5B-34 H H H H H CH2C6H5B-35 H H H CH3H CH2C6H5B-36 H H H C2H5H CH2C6H5B-37 H H H CH2C6H5H CH2C6H5B-38 H H CH3CH3H CH2C6H5B-39 H H CH3C2H5H CH2C6H5B-40 H H CH3CH2C6H5H CH2C6H5B-41 H H C2H5C2H5H CH2C6H5B-42 H H C2H5CH2C6H5H CH2C6H5B-43 H H CH2C6H5CH2C6H5H CH2C6H5B-44 H H -CH2-CH2- H CH2C6H5B-45 H H H H CH3CH3B-46 H H H CH3CH3CH3B-47 H H H C2H5CH3CH3B-48 H H H CH2C6H5CH3CH3B-49 H H CH3CH3CH3CH3B-50 H H CH3C2H5CH3CH3B-51 H H CH3CH2C6H5CH3CH3B-52 H H C2H5C2H5CH3CH3B-53 H H C2H5CH2C6H5CH3CH3B-54 H H CH2C6H5CH2C6H5CH3CH3

[0663]

[0664] 250444W001

[0665] 35

[0666] No. X1X2R5R6R7R8B-55 H H -CH2-CH2- CH3CH3B-56 H H H H CH3C2H5B-57 H H H CH3CH3C2H5B-58 H H H C2H5CH3C2H5B-59 H H H CH2C6H5CH3C2H5B-60 H H CH3CH3CH3C2H5B-61 H H CH3C2H5CH3C2H5B-62 H H CH3CH2C6H5CH3C2H5B-63 H H C2H5C2H5CH3C2H5B-64 H H C2H5CH2C6H5CH3C2H5B-65 H H CH2C6H5CH2C6H5CH3C2H5B-66 H H -CH2-CH2- CH3C2H5B-67 H H H H CH3CH2C6H5B-68 H H H CH3CH3CH2C6H5B-69 H H H C2H5CH3CH2C6H5B-70 H H H CH2C6H5CH3CH2C6H5B-71 H H CH3CH3CH3CH2C6H5B-72 H H CH3C2H5CH3CH2C6H5B-73 H H CH3CH2C6H5CH3CH2C6H5B-74 H H C2H5C2H5CH3CH2C6H5B-75 H H C2H5CH2C6H5CH3CH2C6H5B-76 H H CH2C6H5CH2C6H5CH3CH2C6H5B-77 H H -CH2-CH2- CH3CH2C6H5B-78 H H H H C2H5C2H5B-79 H H H CH3C2H5C2H5B-80 H H H C2H5C2H5C2H5B-81 H H H CH2C6H5C2H5C2H5

[0667]

[0668] 250444W001

[0669] 36

[0670] No. X1X2R5R6R7R8B-82 H H CH3CH3C2H5C2H5B-83 H H CH3C2H5C2H5C2H5B-84 H H CH3CH2C6H5C2H5C2H5B-85 H H C2H5C2H5C2H5C2H5B-86 H H C2H5CH2C6H5C2H5C2H5B-87 H H CH2C6H5CH2C6H5C2H5C2H5B-88 H H -CH2-CH2- C2H5C2H5B-89 H H H H C2H5CH2C6H5B-90 H H H CH3C2H5CH2C6H5B-91 H H H C2H5C2H5CH2C6H5B-92 H H H CH2C6H5C2H5CH2C6H5B-93 H H CH3CH3C2H5CH2C6H5B-94 H H CH3C2H5C2H5CH2C6H5B-95 H H CH3CH2C6H5C2H5CH2C6H5B-96 H H C2H5C2H5C2H5CH2C6H5B-97 H H C2H5CH2C6H5C2H5CH2C6H5B-98 H H CH2C6H5CH2C6H5C2H5CH2C6H5B-99 H H -CH2-CH2- C2H5CH2C6H5B-100 H H H H CH2C6H5CH2C6H5B-101 H H H CH3CH2C6H5CH2C6H5B-102 H H H C2H5CH2C6H5CH2C6H5B-103 H H H CH2C6H5CH2C6H5CH2C6H5B-104 H H CH3CH3CH2C6H5CH2C6H5B-105 H H CH3C2H5CH2C6H5CH2C6H5B-106 H H CH3CH2C6H5CH2C6H5CH2C6H5B-107 H H C2H5C2H5CH2C6H5CH2C6H5B-108 H H C2H5CH2C6H5CH2C6H5CH2C6H5

[0671]

[0672] 250444W001

[0673] 37

[0674] No. X1X2R5R6R7R8B-109 H H CH2C6H5CH2C6H5CH2C6H5CH2C6H5B-110 H H -CH2-CH2- CH2C6H5CH2C6H5B-111 H H H H -CH2-CH2- B-112 H H H CH3-CH2-CH2- B-113 H H H C2H5-CH2-CH2- B-114 H H H CH2C6H5-CH2-CH2- B-115 H H CH3CH3-CH2-CH2- B-116 H H CH3C2H5-CH2-CH2- B-117 H H CH3CH2C6H5-CH2-CH2- B-118 H H C2H5C2H5-CH2-CH2- B-119 H H C2H5CH2C6H5-CH2-CH2- B-120 H H CH2C6H5CH2C6H5-CH2-CH2- B-121 H H -CH2-CH2- -CH2-CH2- B-122 H F H H H H B-123 H F H CH3H H B-124 H F H C2H5H H B-125 H F H CH2C6H5H H B-126 H F CH3CH3H H B-127 H F CH3C2H5H H B-128 H F CH3CH2C6H5H H B-129 H F C2H5C2H5H H B-130 H F C2H5CH2C6H5H H B-131 H F CH2C6H5CH2C6H5H H B-132 H F -CH2-CH2- H H B-133 H F H H H CH3B-134 H F H CH3H CH3B-135 H F H C2H5H CH3

[0675]

[0676] 250444W001

[0677] 38

[0678] No. X1X2R5R6R7R8B-136 H F H CH2C6H5H CH3B-137 H F CH3CH3H CH3B-138 H F CH3C2H5H CH3B-139 H F CH3CH2C6H5H CH3B-140 H F C2H5C2H5H CH3B-141 H F C2H5CH2C6H5H CH3B-142 H F CH2C6H5CH2C6H5H CH3B-143 H F -CH2-CH2- H CH3B-144 H F H H H C2H5B-145 H F H CH3H C2H5B-146 H F H C2H5H C2H5B-147 H F H CH2C6H5H C2H5B-148 H F CH3CH3H C2H5B-149 H F CH3C2H5H C2H5B-150 H F CH3CH2C6H5H C2H5B-151 H F C2H5C2H5H C2H5B-152 H F C2H5CH2C6H5H C2H5B-153 H F CH2C6H5CH2C6H5H C2H5B-154 H F -CH2-CH2- H C2H5B-155 H F H H H CH2C6H5B-156 H F H CH3H CH2C6H5B-157 H F H C2H5H CH2C6H5B-158 H F H CH2C6H5H CH2C6H5B-159 H F CH3CH3H CH2C6H5B-160 H F CH3C2H5H CH2C6H5B-161 H F CH3CH2C6H5H CH2C6H5B-162 H F C2H5C2H5H CH2C6H5

[0679]

[0680] 250444W001

[0681] 39

[0682] No. X1X2R5R6R7R8B-163 H F C2H5CH2C6H5H CH2C6H5B-164 H F CH2C6H5CH2C6H5H CH2C6H5B-165 H F -CH2-CH2- H CH2C6H5B-166 H F H H CH3CH3B-167 H F H CH3CH3CH3B-168 H F H C2H5CH3CH3B-169 H F H CH2C6H5CH3CH3B-170 H F CH3CH3CH3CH3B-171 H F CH3C2H5CH3CH3B-172 H F CH3CH2C6H5CH3CH3B-173 H F C2H5C2H5CH3CH3B-174 H F C2H5CH2C6H5CH3CH3B-175 H F CH2C6H5CH2C6H5CH3CH3B-176 H F -CH2-CH2- CH3CH3B-177 H F H H CH3C2H5B-178 H F H CH3CH3C2H5B-179 H F H C2H5CH3C2H5B-180 H F H CH2C6H5CH3C2H5B-181 H F CH3CH3CH3C2H5B-182 H F CH3C2H5CH3C2H5B-183 H F CH3CH2C6H5CH3C2H5B-184 H F C2H5C2H5CH3C2H5B-185 H F C2H5CH2C6H5CH3C2H5B-186 H F CH2C6H5CH2C6H5CH3C2H5B-187 H F -CH2-CH2- CH3C2H5B-188 H F H H CH3CH2C6H5B-189 H F H CH3CH3CH2C6H5

[0683]

[0684] 250444W001

[0685] 40

[0686] No. X1X2R5R6R7R8B-190 H F H C2H5CH3CH2C6H5B-191 H F H CH2C6H5CH3CH2C6H5B-192 H F CH3CH3CH3CH2C6H5B-193 H F CH3C2H5CH3CH2C6H5B-194 H F CH3CH2C6H5CH3CH2C6H5B-195 H F C2H5C2H5CH3CH2C6H5B-196 H F C2H5CH2C6H5CH3CH2C6H5B-197 H F CH2C6H5CH2C6H5CH3CH2C6H5B-198 H F -CH2-CH2- CH3CH2C6H5B-199 H F H H C2H5C2H5B-200 H F H CH3C2H5C2H5B-201 H F H C2H5C2H5C2H5B-202 H F H CH2C6H5C2H5C2H5B-203 H F CH3CH3C2H5C2H5B-204 H F CH3C2H5C2H5C2H5B-205 H F CH3CH2C6H5C2H5C2H5B-206 H F C2H5C2H5C2H5C2H5B-207 H F C2H5CH2C6H5C2H5C2H5B-208 H F CH2C6H5CH2C6H5C2H5C2H5B-209 H F -CH2-CH2- C2H5C2H5B-210 H F H H C2H5CH2C6H5B-211 H F H CH3C2H5CH2C6H5B-212 H F H C2H5C2H5CH2C6H5B-213 H F H CH2C6H5C2H5CH2C6H5B-214 H F CH3CH3C2H5CH2C6H5B-215 H F CH3C2H5C2H5CH2C6H5B-216 H F CH3CH2C6H5C2H5CH2C6H5

[0687]

[0688] 250444W001

[0689] 41

[0690] No. X1X2R5R6R7R8B-217 H F C2H5C2H5C2H5CH2C6H5B-218 H F C2H5CH2C6H5C2H5CH2C6H5B-219 H F CH2C6H5CH2C6H5C2H5CH2C6H5B-220 H F -CH2-CH2- C2H5CH2C6H5B-221 H F H H CH2C6H5CH2C6H5B-222 H F H CH3CH2C6H5CH2C6H5B-223 H F H C2H5CH2C6H5CH2C6H5B-224 H F H CH2C6H5CH2C6H5CH2C6H5B-225 H F CH3CH3CH2C6H5CH2C6H5B-226 H F CH3C2H5CH2C6H5CH2C6H5B-227 H F CH3CH2C6H5CH2C6H5CH2C6H5B-228 H F C2H5C2H5CH2C6H5CH2C6H5B-229 H F C2H5CH2C6H5CH2C6H5CH2C6H5B-230 H F CH2C6H5CH2C6H5CH2C6H5CH2C6H5B-231 H F -CH2-CH2- CH2C6H5CH2C6H5B-232 H F H H -CH2-CH2- B-233 H F H CH3-CH2-CH2- B-234 H F H C2H5-CH2-CH2- B-235 H F H CH2C6H5-CH2-CH2- B-236 H F CH3CH3-CH2-CH2- B-237 H F CH3C2H5-CH2-CH2- B-238 H F CH3CH2C6H5-CH2-CH2- B-239 H F C2H5C2H5-CH2-CH2- B-240 H F C2H5CH2C6H5-CH2-CH2- B-241 H F CH2C6H5CH2C6H5-CH2-CH2- B-242 H F -CH2-CH2- -CH2-CH2- B-243 F H H H H H

[0691]

[0692] 250444W001

[0693] 42

[0694] No. X1X2R5R6R7R8B-244 F H H CH3H H B-245 F H H C2H5H H B-246 F H H CH2C6H5H H B-247 F H CH3CH3H H B-248 F H CH3C2H5H H B-249 F H CH3CH2C6H5H H B-250 F H C2H5C2H5H H B-251 F H C2H5CH2C6H5H H B-252 F H CH2C6H5CH2C6H5H H B-253 F H -CH2-CH2- H H B-254 F H H H H CH3B-255 F H H CH3H CH3B-256 F H H C2H5H CH3B-257 F H H CH2C6H5H CH3B-258 F H CH3CH3H CH3B-259 F H CH3C2H5H CH3B-260 F H CH3CH2C6H5H CH3B-261 F H C2H5C2H5H CH3B-262 F H C2H5CH2C6H5H CH3B-263 F H CH2C6H5CH2C6H5H CH3B-264 F H -CH2-CH2- H CH3B-265 F H H H H C2H5B-266 F H H CH3H C2H5B-267 F H H C2H5H C2H5B-268 F H H CH2C6H5H C2H5B-269 F H CH3CH3H C2H5B-270 F H CH3C2H5H C2H5

[0695]

[0696] 250444W001

[0697] 43

[0698] No. X1X2R5R6R7R8B-271 F H CH3CH2C6H5H C2H5B-272 F H C2H5C2H5H C2H5B-273 F H C2H5CH2C6H5H C2H5B-274 F H CH2C6H5CH2C6H5H C2H5B-275 F H -CH2-CH2- H C2H5B-276 F H H H H CH2C6H5B-277 F H H CH3H CH2C6H5B-278 F H H C2H5H CH2C6H5B-279 F H H CH2C6H5H CH2C6H5B-280 F H CH3CH3H CH2C6H5B-281 F H CH3C2H5H CH2C6H5B-282 F H CH3CH2C6H5H CH2C6H5B-283 F H C2H5C2H5H CH2C6H5B-284 F H C2H5CH2C6H5H CH2C6H5B-285 F H CH2C6H5CH2C6H5H CH2C6H5B-286 F H -CH2-CH2- H CH2C6H5B-287 F H H H CH3CH3B-288 F H H CH3CH3CH3B-289 F H H C2H5CH3CH3B-290 F H H CH2C6H5CH3CH3B-291 F H CH3CH3CH3CH3B-292 F H CH3C2H5CH3CH3B-293 F H CH3CH2C6H5CH3CH3B-294 F H C2H5C2H5CH3CH3B-295 F H C2H5CH2C6H5CH3CH3B-296 F H CH2C6H5CH2C6H5CH3CH3B-297 F H -CH2-CH2- CH3CH3

[0699]

[0700] 250444W001

[0701] 44

[0702] No. X1X2R5R6R7R8B-298 F H H H CH3C2H5B-299 F H H CH3CH3C2H5B-300 F H H C2H5CH3C2H5B-301 F H H CH2C6H5CH3C2H5B-302 F H CH3CH3CH3C2H5B-303 F H CH3C2H5CH3C2H5B-304 F H CH3CH2C6H5CH3C2H5B-305 F H C2H5C2H5CH3C2H5B-306 F H C2H5CH2C6H5CH3C2H5B-307 F H CH2C6H5CH2C6H5CH3C2H5B-308 F H -CH2-CH2- CH3C2H5B-309 F H H H CH3CH2C6H5B-310 F H H CH3CH3CH2C6H5B-311 F H H C2H5CH3CH2C6H5B-312 F H H CH2C6H5CH3CH2C6H5B-313 F H CH3CH3CH3CH2C6H5B-314 F H CH3C2H5CH3CH2C6H5B-315 F H CH3CH2C6H5CH3CH2C6H5B-316 F H C2H5C2H5CH3CH2C6H5B-317 F H C2H5CH2C6H5CH3CH2C6H5B-318 F H CH2C6H5CH2C6H5CH3CH2C6H5B-319 F H -CH2-CH2- CH3CH2C6H5B-320 F H H H C2H5C2H5B-321 F H H CH3C2H5C2H5B-322 F H H C2H5C2H5C2H5B-323 F H H CH2C6H5C2H5C2H5B-324 F H CH3CH3C2H5C2H5

[0703]

[0704] 250444W001

[0705] 45

[0706] No. X1X2R5R6R7R8B-325 F H CH3C2H5C2H5C2H5B-326 F H CH3CH2C6H5C2H5C2H5B-327 F H C2H5C2H5C2H5C2H5B-328 F H C2H5CH2C6H5C2H5C2H5B-329 F H CH2C6H5CH2C6H5C2H5C2H5B-330 F H -CH2-CH2- C2H5C2H5B-331 F H H H C2H5CH2C6H5B-332 F H H CH3C2H5CH2C6H5B-333 F H H C2H5C2H5CH2C6H5B-334 F H H CH2C6H5C2H5CH2C6H5B-335 F H CH3CH3C2H5CH2C6H5B-336 F H CH3C2H5C2H5CH2C6H5B-337 F H CH3CH2C6H5C2H5CH2C6H5B-338 F H C2H5C2H5C2H5CH2C6H5B-339 F H C2H5CH2C6H5C2H5CH2C6H5B-340 F H CH2C6H5CH2C6H5C2H5CH2C6H5B-341 F H -CH2-CH2- C2H5CH2C6H5B-342 F H H H CH2C6H5CH2C6H5B-343 F H H CH3CH2C6H5CH2C6H5B-344 F H H C2H5CH2C6H5CH2C6H5B-345 F H H CH2C6H5CH2C6H5CH2C6H5B-346 F H CH3CH3CH2C6H5CH2C6H5B-347 F H CH3C2H5CH2C6H5CH2C6H5B-348 F H CH3CH2C6H5CH2C6H5CH2C6H5B-349 F H C2H5C2H5CH2C6H5CH2C6H5B-350 F H C2H5CH2C6H5CH2C6H5CH2C6H5B-351 F H CH2C6H5CH2C6H5CH2C6H5CH2C6H5

[0707]

[0708] 250444W001

[0709] 46

[0710] No. X1X2R5R6R7R8B-352 F H -CH2-CH2- CH2C6H5CH2C6H5B-353 F H H H -CH2-CH2- B-354 F H H CH3-CH2-CH2- B-355 F H H C2H5-CH2-CH2- B-356 F H H CH2C6H5-CH2-CH2- B-357 F H CH3CH3-CH2-CH2- B-358 F H CH3C2H5-CH2-CH2- B-359 F H CH3CH2C6H5-CH2-CH2- B-360 F H C2H5C2H5-CH2-CH2- B-361 F H C2H5CH2C6H5-CH2-CH2- B-362 F H CH2C6H5CH2C6H5-CH2-CH2- B-363 F H -CH2-CH2- -CH2-CH2- B-364 H Cl H H H H B-365 H Cl H CH3H H B-366 H Cl H C2H5H H B-367 H Cl H CH2C6H5H H B-368 H Cl CH3CH3H H B-369 H Cl CH3C2H5H H B-370 H Cl CH3CH2C6H5H H B-371 H Cl C2H5C2H5H H B-372 H Cl C2H5CH2C6H5H H B-373 H Cl CH2C6H5CH2C6H5H H B-374 H Cl -CH2-CH2- H H B-375 H Cl H H H CH3B-376 H Cl H CH3H CH3B-377 H Cl H C2H5H CH3B-378 H Cl H CH2C6H5H CH3

[0711]

[0712] 250444W001

[0713] 47

[0714] No. X1X2R5R6R7R8B-379 H Cl CH3CH3H CH3B-380 H Cl CH3C2H5H CH3B-381 H Cl CH3CH2C6H5H CH3B-382 H Cl C2H5C2H5H CH3B-383 H Cl C2H5CH2C6H5H CH3B-384 H Cl CH2C6H5CH2C6H5H CH3B-385 H Cl -CH2-CH2- H CH3B-386 H Cl H H H C2H5B-387 H Cl H CH3H C2H5B-388 H Cl H C2H5H C2H5B-389 H Cl H CH2C6H5H C2H5B-390 H Cl CH3CH3H C2H5B-391 H Cl CH3C2H5H C2H5B-392 H Cl CH3CH2C6H5H C2H5B-393 H Cl C2H5C2H5H C2H5B-394 H Cl C2H5CH2C6H5H C2H5B-395 H Cl CH2C6H5CH2C6H5H C2H5B-396 H Cl -CH2-CH2- H C2H5B-397 H Cl H H H CH2C6H5B-398 H Cl H CH3H CH2C6H5B-399 H Cl H C2H5H CH2C6H5B-400 H Cl H CH2C6H5H CH2C6H5B-401 H Cl CH3CH3H CH2C6H5B-402 H Cl CH3C2H5H CH2C6H5B-403 H Cl CH3CH2C6H5H CH2C6H5B-404 H Cl C2H5C2H5H CH2C6H5B-405 H Cl C2H5CH2C6H5H CH2C6H5

[0715]

[0716] 250444W001

[0717] 48

[0718] No. X1X2R5R6R7R8B-406 H Cl CH2C6H5CH2C6H5H CH2C6H5B-407 H Cl -CH2-CH2- H CH2C6H5B-408 H Cl H H CH3CH3B-409 H Cl H CH3CH3CH3B-410 H Cl H C2H5CH3CH3B-411 H Cl H CH2C6H5CH3CH3B-412 H Cl CH3CH3CH3CH3B-413 H Cl CH3C2H5CH3CH3B-414 H Cl CH3CH2C6H5CH3CH3B-415 H Cl C2H5C2H5CH3CH3B-416 H Cl C2H5CH2C6H5CH3CH3B-417 H Cl CH2C6H5CH2C6H5CH3CH3B-418 H Cl -CH2-CH2- CH3CH3B-419 H Cl H H CH3C2H5B-420 H Cl H CH3CH3C2H5B-421 H Cl H C2H5CH3C2H5B-422 H Cl H CH2C6H5CH3C2H5B-423 H Cl CH3CH3CH3C2H5B-424 H Cl CH3C2H5CH3C2H5B-425 H Cl CH3CH2C6H5CH3C2H5B-426 H Cl C2H5C2H5CH3C2H5B-427 H Cl C2H5CH2C6H5CH3C2H5B-428 H Cl CH2C6H5CH2C6H5CH3C2H5B-429 H Cl -CH2-CH2- CH3C2H5B-430 H Cl H H CH3CH2C6H5B-431 H Cl H CH3CH3CH2C6H5B-432 H Cl H C2H5CH3CH2C6H5

[0719]

[0720] 250444W001

[0721] 49

[0722] No. X1X2R5R6R7R8B-433 H Cl H CH2C6H5CH3CH2C6H5B-434 H Cl CH3CH3CH3CH2C6H5B-435 H Cl CH3C2H5CH3CH2C6H5B-436 H Cl CH3CH2C6H5CH3CH2C6H5B-437 H Cl C2H5C2H5CH3CH2C6H5B-438 H Cl C2H5CH2C6H5CH3CH2C6H5B-439 H Cl CH2C6H5CH2C6H5CH3CH2C6H5B-440 H Cl -CH2-CH2- CH3CH2C6H5B-441 H Cl H H C2H5C2H5B-442 H Cl H CH3C2H5C2H5B-443 H Cl H C2H5C2H5C2H5B-444 H Cl H CH2C6H5C2H5C2H5B-445 H Cl CH3CH3C2H5C2H5B-446 H Cl CH3C2H5C2H5C2H5B-447 H Cl CH3CH2C6H5C2H5C2H5B-448 H Cl C2H5C2H5C2H5C2H5B-449 H Cl C2H5CH2C6H5C2H5C2H5B-450 H Cl CH2C6H5CH2C6H5C2H5C2H5B-451 H Cl -CH2-CH2- C2H5C2H5B-452 H Cl H H C2H5CH2C6H5B-453 H Cl H CH3C2H5CH2C6H5B-454 H Cl H C2H5C2H5CH2C6H5B-455 H Cl H CH2C6H5C2H5CH2C6H5B-456 H Cl CH3CH3C2H5CH2C6H5B-457 H Cl CH3C2H5C2H5CH2C6H5B-458 H Cl CH3CH2C6H5C2H5CH2C6H5B-459 H Cl C2H5C2H5C2H5CH2C6H5

[0723]

[0724] 250444W001

[0725] 50

[0726] No. X1X2R5R6R7R8B-460 H Cl C2H5CH2C6H5C2H5CH2C6H5B-461 H Cl CH2C6H5CH2C6H5C2H5CH2C6H5B-462 H Cl -CH2-CH2- C2H5CH2C6H5B-463 H Cl H H CH2C6H5CH2C6H5B-464 H Cl H CH3CH2C6H5CH2C6H5B-465 H Cl H C2H5CH2C6H5CH2C6H5B-466 H Cl H CH2C6H5CH2C6H5CH2C6H5B-467 H Cl CH3CH3CH2C6H5CH2C6H5B-468 H Cl CH3C2H5CH2C6H5CH2C6H5B-469 H Cl CH3CH2C6H5CH2C6H5CH2C6H5B-470 H Cl C2H5C2H5CH2C6H5CH2C6H5B-471 H Cl C2H5CH2C6H5CH2C6H5CH2C6H5B-472 H Cl CH2C6H5CH2C6H5CH2C6H5CH2C6H5B-473 H Cl -CH2-CH2- CH2C6H5CH2C6H5B-474 H Cl H H -CH2-CH2- B-475 H Cl H CH3-CH2-CH2- B-476 H Cl H C2H5-CH2-CH2- B-477 H Cl H CH2C6H5-CH2-CH2- B-478 H Cl CH3CH3-CH2-CH2- B-479 H Cl CH3C2H5-CH2-CH2- B-480 H Cl CH3CH2C6H5-CH2-CH2- B-481 H Cl C2H5C2H5-CH2-CH2- B-482 H Cl C2H5CH2C6H5-CH2-CH2- B-483 H Cl CH2C6H5CH2C6H5-CH2-CH2- B-484 H Cl -CH2-CH2- -CH2-CH2- B-485 Cl H H H H H B-486 Cl H H CH3H H

[0727]

[0728] 250444W001

[0729] 51

[0730] No. X1X2R5R6R7R8B-487 Cl H H C2H5H H B-488 Cl H H CH2C6H5H H B-489 Cl H CH3CH3H H B-490 Cl H CH3C2H5H H B-491 Cl H CH3CH2C6H5H H B-492 Cl H C2H5C2H5H H B-493 Cl H C2H5CH2C6H5H H B-494 Cl H CH2C6H5CH2C6H5H H B-495 Cl H -CH2-CH2- H H B-496 Cl H H H H CH3B-497 Cl H H CH3H CH3B-498 Cl H H C2H5H CH3B-499 Cl H H CH2C6H5H CH3B-500 Cl H CH3CH3H CH3B-501 Cl H CH3C2H5H CH3B-502 Cl H CH3CH2C6H5H CH3B-503 Cl H C2H5C2H5H CH3B-504 Cl H C2H5CH2C6H5H CH3B-505 Cl H CH2C6H5CH2C6H5H CH3B-506 Cl H -CH2-CH2- H CH3B-507 Cl H H H H C2H5B-508 Cl H H CH3H C2H5B-509 Cl H H C2H5H C2H5B-510 Cl H H CH2C6H5H C2H5B-511 Cl H CH3CH3H C2H5B-512 Cl H CH3C2H5H C2H5B-513 Cl H CH3CH2C6H5H C2H5

[0731]

[0732] 250444W001

[0733] 52

[0734] No. X1X2R5R6R7R8B-514 Cl H C2H5C2H5H C2H5B-515 Cl H C2H5CH2C6H5H C2H5B-516 Cl H CH2C6H5CH2C6H5H C2H5B-517 Cl H -CH2-CH2- H C2H5B-518 Cl H H H H CH2C6H5B-519 Cl H H CH3H CH2C6H5B-520 Cl H H C2H5H CH2C6H5B-521 Cl H H CH2C6H5H CH2C6H5B-522 Cl H CH3CH3H CH2C6H5B-523 Cl H CH3C2H5H CH2C6H5B-524 Cl H CH3CH2C6H5H CH2C6H5B-525 Cl H C2H5C2H5H CH2C6H5B-526 Cl H C2H5CH2C6H5H CH2C6H5B-527 Cl H CH2C6H5CH2C6H5H CH2C6H5B-528 Cl H -CH2-CH2- H CH2C6H5B-529 Cl H H H CH3CH3B-530 Cl H H CH3CH3CH3B-531 Cl H H C2H5CH3CH3B-532 Cl H H CH2C6H5CH3CH3B-533 Cl H CH3CH3CH3CH3B-534 Cl H CH3C2H5CH3CH3B-535 Cl H CH3CH2C6H5CH3CH3B-536 Cl H C2H5C2H5CH3CH3B-537 Cl H C2H5CH2C6H5CH3CH3B-538 Cl H CH2C6H5CH2C6H5CH3CH3B-539 Cl H -CH2-CH2- CH3CH3B-540 Cl H H H CH3C2H5

[0735]

[0736] 250444W001

[0737] 53

[0738] No. X1X2R5R6R7R8B-541 Cl H H CH3CH3C2H5B-542 Cl H H C2H5CH3C2H5B-543 Cl H H CH2C6H5CH3C2H5B-544 Cl H CH3CH3CH3C2H5B-545 Cl H CH3C2H5CH3C2H5B-546 Cl H CH3CH2C6H5CH3C2H5B-547 Cl H C2H5C2H5CH3C2H5B-548 Cl H C2H5CH2C6H5CH3C2H5B-549 Cl H CH2C6H5CH2C6H5CH3C2H5B-550 Cl H -CH2-CH2- CH3C2H5B-551 Cl H H H CH3CH2C6H5B-552 Cl H H CH3CH3CH2C6H5B-553 Cl H H C2H5CH3CH2C6H5B-554 Cl H H CH2C6H5CH3CH2C6H5B-555 Cl H CH3CH3CH3CH2C6H5B-556 Cl H CH3C2H5CH3CH2C6H5B-557 Cl H CH3CH2C6H5CH3CH2C6H5B-558 Cl H C2H5C2H5CH3CH2C6H5B-559 Cl H C2H5CH2C6H5CH3CH2C6H5B-560 Cl H CH2C6H5CH2C6H5CH3CH2C6H5B-561 Cl H -CH2-CH2- CH3CH2C6H5B-562 Cl H H H C2H5C2H5B-563 Cl H H CH3C2H5C2H5B-564 Cl H H C2H5C2H5C2H5B-565 Cl H H CH2C6H5C2H5C2H5B-566 Cl H CH3CH3C2H5C2H5B-567 Cl H CH3C2H5C2H5C2H5

[0739]

[0740] 250444W001

[0741] 54

[0742] No. X1X2R5R6R7R8B-568 Cl H CH3CH2C6H5C2H5C2H5B-569 Cl H C2H5C2H5C2H5C2H5B-570 Cl H C2H5CH2C6H5C2H5C2H5B-571 Cl H CH2C6H5CH2C6H5C2H5C2H5B-572 Cl H -CH2-CH2- C2H5C2H5B-573 Cl H H H C2H5CH2C6H5B-574 Cl H H CH3C2H5CH2C6H5B-575 Cl H H C2H5C2H5CH2C6H5B-576 Cl H H CH2C6H5C2H5CH2C6H5B-577 Cl H CH3CH3C2H5CH2C6H5B-578 Cl H CH3C2H5C2H5CH2C6H5B-579 Cl H CH3CH2C6H5C2H5CH2C6H5B-580 Cl H C2H5C2H5C2H5CH2C6H5B-581 Cl H C2H5CH2C6H5C2H5CH2C6H5B-582 Cl H CH2C6H5CH2C6H5C2H5CH2C6H5B-583 Cl H -CH2-CH2- C2H5CH2C6H5B-584 Cl H H H CH2C6H5CH2C6H5B-585 Cl H H CH3CH2C6H5CH2C6H5B-586 Cl H H C2H5CH2C6H5CH2C6H5B-587 Cl H H CH2C6H5CH2C6H5CH2C6H5B-588 Cl H CH3CH3CH2C6H5CH2C6H5B-589 Cl H CH3C2H5CH2C6H5CH2C6H5B-590 Cl H CH3CH2C6H5CH2C6H5CH2C6H5B-591 Cl H C2H5C2H5CH2C6H5CH2C6H5B-592 Cl H C2H5CH2C6H5CH2C6H5CH2C6H5B-593 Cl H CH2C6H5CH2C6H5CH2C6H5CH2C6H5B-594 Cl H -CH2-CH2- CH2C6H5CH2C6H5

[0743]

[0744] 250444W001

[0745] 55

[0746] No. X1X2R5R6R7R8B-595 Cl H H H -CH2-CH2- B-596 Cl H H CH3-CH2-CH2- B-597 Cl H H C2H5-CH2-CH2- B-598 Cl H H CH2C6H5-CH2-CH2- B-599 Cl H CH3CH3-CH2-CH2- B-600 Cl H CH3C2H5-CH2-CH2- B-601 Cl H CH3CH2C6H5-CH2-CH2- B-602 Cl H C2H5C2H5-CH2-CH2- B-603 Cl H C2H5CH2C6H5-CH2-CH2- B-604 Cl H CH2C6H5CH2C6H5-CH2-CH2- B-605 Cl H -CH2-CH2- -CH2-CH2- B-606 F F H H H H B-607 F F H CH3H H B-608 F F H C2H5H H B-609 F F H CH2C6H5H H B-610 F F CH3CH3H H B-611 F F CH3C2H5H H B-612 F F CH3CH2C6H5H H B-613 F F C2H5C2H5H H B-614 F F C2H5CH2C6H5H H B-615 F F CH2C6H5CH2C6H5H H B-616 F F -CH2-CH2- H H B-617 F F H H H CH3B-618 F F H CH3H CH3B-619 F F H C2H5H CH3B-620 F F H CH2C6H5H CH3B-621 F F CH3CH3H CH3

[0747]

[0748] 250444W001

[0749] 56

[0750] No. X1X2R5R6R7R8B-622 F F CH3C2H5H CH3B-623 F F CH3CH2C6H5H CH3B-624 F F C2H5C2H5H CH3B-625 F F C2H5CH2C6H5H CH3B-626 F F CH2C6H5CH2C6H5H CH3B-627 F F -CH2-CH2- H CH3B-628 F F H H H C2H5B-629 F F H CH3H C2H5B-630 F F H C2H5H C2H5B-631 F F H CH2C6H5H C2H5B-632 F F CH3CH3H C2H5B-633 F F CH3C2H5H C2H5B-634 F F CH3CH2C6H5H C2H5B-635 F F C2H5C2H5H C2H5B-636 F F C2H5CH2C6H5H C2H5B-637 F F CH2C6H5CH2C6H5H C2H5B-638 F F -CH2-CH2- H C2H5B-639 F F H H H CH2C6H5B-640 F F H CH3H CH2C6H5B-641 F F H C2H5H CH2C6H5B-642 F F H CH2C6H5H CH2C6H5B-643 F F CH3CH3H CH2C6H5B-644 F F CH3C2H5H CH2C6H5B-645 F F CH3CH2C6H5H CH2C6H5B-646 F F C2H5C2H5H CH2C6H5B-647 F F C2H5CH2C6H5H CH2C6H5B-648 F F CH2C6H5CH2C6H5H CH2C6H5

[0751]

[0752] 250444W001

[0753] 57

[0754] No. X1X2R5R6R7R8B-649 F F -CH2-CH2- H CH2C6H5B-650 F F H H CH3CH3B-651 F F H CH3CH3CH3B-652 F F H C2H5CH3CH3B-653 F F H CH2C6H5CH3CH3B-654 F F CH3CH3CH3CH3B-655 F F CH3C2H5CH3CH3B-656 F F CH3CH2C6H5CH3CH3B-657 F F C2H5C2H5CH3CH3B-658 F F C2H5CH2C6H5CH3CH3B-659 F F CH2C6H5CH2C6H5CH3CH3B-660 F F -CH2-CH2- CH3CH3B-661 F F H H CH3C2H5B-662 F F H CH3CH3C2H5B-663 F F H C2H5CH3C2H5B-664 F F H CH2C6H5CH3C2H5B-665 F F CH3CH3CH3C2H5B-666 F F CH3C2H5CH3C2H5B-667 F F CH3CH2C6H5CH3C2H5B-668 F F C2H5C2H5CH3C2H5B-669 F F C2H5CH2C6H5CH3C2H5B-670 F F CH2C6H5CH2C6H5CH3C2H5B-671 F F -CH2-CH2- CH3C2H5B-672 F F H H CH3CH2C6H5B-673 F F H CH3CH3CH2C6H5B-674 F F H C2H5CH3CH2C6H5B-675 F F H CH2C6H5CH3CH2C6H5

[0755]

[0756] 250444W001

[0757] 58

[0758] No. X1X2R5R6R7R8B-676 F F CH3CH3CH3CH2C6H5B-677 F F CH3C2H5CH3CH2C6H5B-678 F F CH3CH2C6H5CH3CH2C6H5B-679 F F C2H5C2H5CH3CH2C6H5B-680 F F C2H5CH2C6H5CH3CH2C6H5B-681 F F CH2C6H5CH2C6H5CH3CH2C6H5B-682 F F -CH2-CH2- CH3CH2C6H5B-683 F F H H C2H5C2H5B-684 F F H CH3C2H5C2H5B-685 F F H C2H5C2H5C2H5B-686 F F H CH2C6H5C2H5C2H5B-687 F F CH3CH3C2H5C2H5B-688 F F CH3C2H5C2H5C2H5B-689 F F CH3CH2C6H5C2H5C2H5B-690 F F C2H5C2H5C2H5C2H5B-691 F F C2H5CH2C6H5C2H5C2H5B-692 F F CH2C6H5CH2C6H5C2H5C2H5B-693 F F -CH2-CH2- C2H5C2H5B-694 F F H H C2H5CH2C6H5B-695 F F H CH3C2H5CH2C6H5B-696 F F H C2H5C2H5CH2C6H5B-697 F F H CH2C6H5C2H5CH2C6H5B-698 F F CH3CH3C2H5CH2C6H5B-699 F F CH3C2H5C2H5CH2C6H5B-700 F F CH3CH2C6H5C2H5CH2C6H5B-701 F F C2H5C2H5C2H5CH2C6H5B-702 F F C2H5CH2C6H5C2H5CH2C6H5

[0759]

[0760] 250444W001

[0761] 59

[0762] No. X1X2R5R6R7R8B-703 F F CH2C6H5CH2C6H5C2H5CH2C6H5B-704 F F -CH2-CH2- C2H5CH2C6H5B-705 F F H H CH2C6H5CH2C6H5B-706 F F H CH3CH2C6H5CH2C6H5B-707 F F H C2H5CH2C6H5CH2C6H5B-708 F F H CH2C6H5CH2C6H5CH2C6H5B-709 F F CH3CH3CH2C6H5CH2C6H5B-710 F F CH3C2H5CH2C6H5CH2C6H5B-711 F F CH3CH2C6H5CH2C6H5CH2C6H5B-712 F F C2H5C2H5CH2C6H5CH2C6H5B-713 F F C2H5CH2C6H5CH2C6H5CH2C6H5B-714 F F CH2C6H5CH2C6H5CH2C6H5CH2C6H5B-715 F F -CH2-CH2- CH2C6H5CH2C6H5B-716 F F H H -CH2-CH2- B-717 F F H CH3-CH2-CH2- B-718 F F H C2H5-CH2-CH2- B-719 F F H CH2C6H5-CH2-CH2- B-720 F F CH3CH3-CH2-CH2- B-721 F F CH3C2H5-CH2-CH2- B-722 F F CH3CH2C6H5-CH2-CH2- B-723 F F C2H5C2H5-CH2-CH2- B-724 F F C2H5CH2C6H5-CH2-CH2- B-725 F F CH2C6H5CH2C6H5-CH2-CH2- B-726 F F -CH2-CH2- -CH2-CH2- B-727 Cl Cl H H H H B-728 Cl Cl H CH3H H B-729 Cl Cl H C2H5H H

[0763]

[0764] 250444W001

[0765] 60

[0766] No. X1X2R5R6R7R8B-730 Cl Cl H CH2C6H5H H B-731 Cl Cl CH3CH3H H B-732 Cl Cl CH3C2H5H H B-733 Cl Cl CH3CH2C6H5H H B-734 Cl Cl C2H5C2H5H H B-735 Cl Cl C2H5CH2C6H5H H B-736 Cl Cl CH2C6H5CH2C6H5H H B-737 Cl Cl -CH2-CH2- H H B-738 Cl Cl H H H CH3B-739 Cl Cl H CH3H CH3B-740 Cl Cl H C2H5H CH3B-741 Cl Cl H CH2C6H5H CH3B-742 Cl Cl CH3CH3H CH3B-743 Cl Cl CH3C2H5H CH3B-744 Cl Cl CH3CH2C6H5H CH3B-745 Cl Cl C2H5C2H5H CH3B-746 Cl Cl C2H5CH2C6H5H CH3B-747 Cl Cl CH2C6H5CH2C6H5H CH3B-748 Cl Cl -CH2-CH2- H CH3B-749 Cl Cl H H H C2H5B-750 Cl Cl H CH3H C2H5B-751 Cl Cl H C2H5H C2H5B-752 Cl Cl H CH2C6H5H C2H5B-753 Cl Cl CH3CH3H C2H5B-754 Cl Cl CH3C2H5H C2H5B-755 Cl Cl CH3CH2C6H5H C2H5B-756 Cl Cl C2H5C2H5H C2H5

[0767]

[0768] 250444W001

[0769] 61

[0770] No. X1X2R5R6R7R8B-757 Cl Cl C2H5CH2C6H5H C2H5B-758 Cl Cl CH2C6H5CH2C6H5H C2H5B-759 Cl Cl -CH2-CH2- H C2H5B-760 Cl Cl H H H CH2C6H5B-761 Cl Cl H CH3H CH2C6H5B-762 Cl Cl H C2H5H CH2C6H5B-763 Cl Cl H CH2C6H5H CH2C6H5B-764 Cl Cl CH3CH3H CH2C6H5B-765 Cl Cl CH3C2H5H CH2C6H5B-766 Cl Cl CH3CH2C6H5H CH2C6H5B-767 Cl Cl C2H5C2H5H CH2C6H5B-768 Cl Cl C2H5CH2C6H5H CH2C6H5B-769 Cl Cl CH2C6H5CH2C6H5H CH2C6H5B-770 Cl Cl -CH2-CH2- H CH2C6H5B-771 Cl Cl H H CH3CH3B-772 Cl Cl H CH3CH3CH3B-773 Cl Cl H C2H5CH3CH3B-774 Cl Cl H CH2C6H5CH3CH3B-775 Cl Cl CH3CH3CH3CH3B-776 Cl Cl CH3C2H5CH3CH3B-777 Cl Cl CH3CH2C6H5CH3CH3B-778 Cl Cl C2H5C2H5CH3CH3B-779 Cl Cl C2H5CH2C6H5CH3CH3B-780 Cl Cl CH2C6H5CH2C6H5CH3CH3B-781 Cl Cl -CH2-CH2- CH3CH3B-782 Cl Cl H H CH3C2H5B-783 Cl Cl H CH3CH3C2H5

[0771]

[0772] 250444W001

[0773] 62

[0774] No. X1X2R5R6R7R8B-784 Cl Cl H C2H5CH3C2H5B-785 Cl Cl H CH2C6H5CH3C2H5B-786 Cl Cl CH3CH3CH3C2H5B-787 Cl Cl CH3C2H5CH3C2H5B-788 Cl Cl CH3CH2C6H5CH3C2H5B-789 Cl Cl C2H5C2H5CH3C2H5B-790 Cl Cl C2H5CH2C6H5CH3C2H5B-791 Cl Cl CH2C6H5CH2C6H5CH3C2H5B-792 Cl Cl -CH2-CH2- CH3C2H5B-793 Cl Cl H H CH3CH2C6H5B-794 Cl Cl H CH3CH3CH2C6H5B-795 Cl Cl H C2H5CH3CH2C6H5B-796 Cl Cl H CH2C6H5CH3CH2C6H5B-797 Cl Cl CH3CH3CH3CH2C6H5B-798 Cl Cl CH3C2H5CH3CH2C6H5B-799 Cl Cl CH3CH2C6H5CH3CH2C6H5B-800 Cl Cl C2H5C2H5CH3CH2C6H5B-801 Cl Cl C2H5CH2C6H5CH3CH2C6H5B-802 Cl Cl CH2C6H5CH2C6H5CH3CH2C6H5B-803 Cl Cl -CH2-CH2- CH3CH2C6H5B-804 Cl Cl H H C2H5C2H5B-805 Cl Cl H CH3C2H5C2H5B-806 Cl Cl H C2H5C2H5C2H5B-807 Cl Cl H CH2C6H5C2H5C2H5B-808 Cl Cl CH3CH3C2H5C2H5B-809 Cl Cl CH3C2H5C2H5C2H5B-810 Cl Cl CH3CH2C6H5C2H5C2H5

[0775]

[0776] 250444W001

[0777] 63

[0778] No. X1X2R5R6R7R8B-811 Cl Cl C2H5C2H5C2H5C2H5B-812 Cl Cl C2H5CH2C6H5C2H5C2H5B-813 Cl Cl CH2C6H5CH2C6H5C2H5C2H5B-814 Cl Cl -CH2-CH2- C2H5C2H5B-815 Cl Cl H H C2H5CH2C6H5B-816 Cl Cl H CH3C2H5CH2C6H5B-817 Cl Cl H C2H5C2H5CH2C6H5B-818 Cl Cl H CH2C6H5C2H5CH2C6H5B-819 Cl Cl CH3CH3C2H5CH2C6H5B-820 Cl Cl CH3C2H5C2H5CH2C6H5B-821 Cl Cl CH3CH2C6H5C2H5CH2C6H5B-822 Cl Cl C2H5C2H5C2H5CH2C6H5B-823 Cl Cl C2H5CH2C6H5C2H5CH2C6H5B-824 Cl Cl CH2C6H5CH2C6H5C2H5CH2C6H5B-825 Cl Cl -CH2-CH2- C2H5CH2C6H5B-826 Cl Cl H H CH2C6H5CH2C6H5B-827 Cl Cl H CH3CH2C6H5CH2C6H5B-828 Cl Cl H C2H5CH2C6H5CH2C6H5B-829 Cl Cl H CH2C6H5CH2C6H5CH2C6H5B-830 Cl Cl CH3CH3CH2C6H5CH2C6H5B-831 Cl Cl CH3C2H5CH2C6H5CH2C6H5B-832 Cl Cl CH3CH2C6H5CH2C6H5CH2C6H5B-833 Cl Cl C2H5C2H5CH2C6H5CH2C6H5B-834 Cl Cl C2H5CH2C6H5CH2C6H5CH2C6H5B-835 Cl Cl CH2C6H5CH2C6H5CH2C6H5CH2C6H5B-836 Cl Cl -CH2-CH2- CH2C6H5CH2C6H5B-837 Cl Cl H H -CH2-CH2-

[0779]

[0780] 250444W001

[0781] 64

[0782] No. X1X2R5R6R7R8B-838 Cl Cl H CH3-CH2-CH2- B-839 Cl Cl H C2H5-CH2-CH2- B-840 Cl Cl H CH2C6H5-CH2-CH2- B-841 Cl Cl CH3CH3-CH2-CH2- B-842 Cl Cl CH3C2H5-CH2-CH2- B-843 Cl Cl CH3CH2C6H5-CH2-CH2- B-844 Cl Cl C2H5C2H5-CH2-CH2- B-845 Cl Cl C2H5CH2C6H5-CH2-CH2- B-846 Cl Cl CH2C6H5CH2C6H5-CH2-CH2- B-847 Cl Cl -CH2-CH2- -CH2-CH2- B-848 F Cl H H H H B-849 F Cl H CH3H H B-850 F Cl H C2H5H H B-851 F Cl H CH2C6H5H H B-852 F Cl CH3CH3H H B-853 F Cl CH3C2H5H H B-854 F Cl CH3CH2C6H5H H B-855 F Cl C2H5C2H5H H B-856 F Cl C2H5CH2C6H5H H B-857 F Cl CH2C6H5CH2C6H5H H B-858 F Cl -CH2-CH2- H H B-859 F Cl H H H CH3B-860 F Cl H CH3H CH3B-861 F Cl H C2H5H CH3B-862 F Cl H CH2C6H5H CH3B-863 F Cl CH3CH3H CH3B-864 F Cl CH3C2H5H CH3

[0783]

[0784] 250444W001

[0785] 65

[0786] No. X1X2R5R6R7R8B-865 F Cl CH3CH2C6H5H CH3B-866 F Cl C2H5C2H5H CH3B-867 F Cl C2H5CH2C6H5H CH3B-868 F Cl CH2C6H5CH2C6H5H CH3B-869 F Cl -CH2-CH2- H CH3B-870 F Cl H H H C2H5B-871 F Cl H CH3H C2H5B-872 F Cl H C2H5H C2H5B-873 F Cl H CH2C6H5H C2H5B-874 F Cl CH3CH3H C2H5B-875 F Cl CH3C2H5H C2H5B-876 F Cl CH3CH2C6H5H C2H5B-877 F Cl C2H5C2H5H C2H5B-878 F Cl C2H5CH2C6H5H C2H5B-879 F Cl CH2C6H5CH2C6H5H C2H5B-880 F Cl -CH2-CH2- H C2H5B-881 F Cl H H H CH2C6H5B-882 F Cl H CH3H CH2C6H5B-883 F Cl H C2H5H CH2C6H5B-884 F Cl H CH2C6H5H CH2C6H5B-885 F Cl CH3CH3H CH2C6H5B-886 F Cl CH3C2H5H CH2C6H5B-887 F Cl CH3CH2C6H5H CH2C6H5B-888 F Cl C2H5C2H5H CH2C6H5B-889 F Cl C2H5CH2C6H5H CH2C6H5B-890 F Cl CH2C6H5CH2C6H5H CH2C6H5B-891 F Cl -CH2-CH2- H CH2C6H5

[0787]

[0788] 250444W001

[0789] 66

[0790] No. X1X2R5R6R7R8B-892 F Cl H H CH3CH3B-893 F Cl H CH3CH3CH3B-894 F Cl H C2H5CH3CH3B-895 F Cl H CH2C6H5CH3CH3B-896 F Cl CH3CH3CH3CH3B-897 F Cl CH3C2H5CH3CH3B-898 F Cl CH3CH2C6H5CH3CH3B-899 F Cl C2H5C2H5CH3CH3B-900 F Cl C2H5CH2C6H5CH3CH3B-901 F Cl CH2C6H5CH2C6H5CH3CH3B-902 F Cl -CH2-CH2- CH3CH3B-903 F Cl H H CH3C2H5B-904 F Cl H CH3CH3C2H5B-905 F Cl H C2H5CH3C2H5B-906 F Cl H CH2C6H5CH3C2H5B-907 F Cl CH3CH3CH3C2H5B-908 F Cl CH3C2H5CH3C2H5B-909 F Cl CH3CH2C6H5CH3C2H5B-910 F Cl C2H5C2H5CH3C2H5B-911 F Cl C2H5CH2C6H5CH3C2H5B-912 F Cl CH2C6H5CH2C6H5CH3C2H5B-913 F Cl -CH2-CH2- CH3C2H5B-914 F Cl H H CH3CH2C6H5B-915 F Cl H CH3CH3CH2C6H5B-916 F Cl H C2H5CH3CH2C6H5B-917 F Cl H CH2C6H5CH3CH2C6H5B-918 F Cl CH3CH3CH3CH2C6H5

[0791]

[0792] 250444W001

[0793] 67

[0794] No. X1X2R5R6R7R8B-919 F Cl CH3C2H5CH3CH2C6H5B-920 F Cl CH3CH2C6H5CH3CH2C6H5B-921 F Cl C2H5C2H5CH3CH2C6H5B-922 F Cl C2H5CH2C6H5CH3CH2C6H5B-923 F Cl CH2C6H5CH2C6H5CH3CH2C6H5B-924 F Cl -CH2-CH2- CH3CH2C6H5B-925 F Cl H H C2H5C2H5B-926 F Cl H CH3C2H5C2H5B-927 F Cl H C2H5C2H5C2H5B-928 F Cl H CH2C6H5C2H5C2H5B-929 F Cl CH3CH3C2H5C2H5B-930 F Cl CH3C2H5C2H5C2H5B-931 F Cl CH3CH2C6H5C2H5C2H5B-932 F Cl C2H5C2H5C2H5C2H5B-933 F Cl C2H5CH2C6H5C2H5C2H5B-934 F Cl CH2C6H5CH2C6H5C2H5C2H5B-935 F Cl -CH2-CH2- C2H5C2H5B-936 F Cl H H C2H5CH2C6H5B-937 F Cl H CH3C2H5CH2C6H5B-938 F Cl H C2H5C2H5CH2C6H5B-939 F Cl H CH2C6H5C2H5CH2C6H5B-940 F Cl CH3CH3C2H5CH2C6H5B-941 F Cl CH3C2H5C2H5CH2C6H5B-942 F Cl CH3CH2C6H5C2H5CH2C6H5B-943 F Cl C2H5C2H5C2H5CH2C6H5B-944 F Cl C2H5CH2C6H5C2H5CH2C6H5B-945 F Cl CH2C6H5CH2C6H5C2H5CH2C6H5

[0795]

[0796] 250444W001

[0797] 68

[0798] No. X1X2R5R6R7R8B-946 F Cl -CH2-CH2- C2H5CH2C6H5B-947 F Cl H H CH2C6H5CH2C6H5B-948 F Cl H CH3CH2C6H5CH2C6H5B-949 F Cl H C2H5CH2C6H5CH2C6H5B-950 F Cl H CH2C6H5CH2C6H5CH2C6H5B-951 F Cl CH3CH3CH2C6H5CH2C6H5B-952 F Cl CH3C2H5CH2C6H5CH2C6H5B-953 F Cl CH3CH2C6H5CH2C6H5CH2C6H5B-954 F Cl C2H5C2H5CH2C6H5CH2C6H5B-955 F Cl C2H5CH2C6H5CH2C6H5CH2C6H5B-956 F Cl CH2C6H5CH2C6H5CH2C6H5CH2C6H5B-957 F Cl -CH2-CH2- CH2C6H5CH2C6H5B-958 F Cl H H -CH2-CH2- B-959 F Cl H CH3-CH2-CH2- B-960 F Cl H C2H5-CH2-CH2- B-961 F Cl H CH2C6H5-CH2-CH2- B-962 F Cl CH3CH3-CH2-CH2- B-963 F Cl CH3C2H5-CH2-CH2- B-964 F Cl CH3CH2C6H5-CH2-CH2- B-965 F Cl C2H5C2H5-CH2-CH2- B-966 F Cl C2H5CH2C6H5-CH2-CH2- B-967 F Cl CH2C6H5CH2C6H5-CH2-CH2- B-968 F Cl -CH2-CH2- -CH2-CH2- B-969 Cl F H H H H B-970 Cl F H CH3H H B-971 Cl F H C2H5H H B-972 Cl F H CH2C6H5H H

[0799]

[0800] 250444W001

[0801] 69

[0802] No. X1X2R5R6R7R8B-973 Cl F CH3CH3H H B-974 Cl F CH3C2H5H H B-975 Cl F CH3CH2C6H5H H B-976 Cl F C2H5C2H5H H B-977 Cl F C2H5CH2C6H5H H B-978 Cl F CH2C6H5CH2C6H5H H B-979 Cl F -CH2-CH2- H H B-980 Cl F H H H CH3B-981 Cl F H CH3H CH3B-982 Cl F H C2H5H CH3B-983 Cl F H CH2C6H5H CH3B-984 Cl F CH3CH3H CH3B-985 Cl F CH3C2H5H CH3B-986 Cl F CH3CH2C6H5H CH3B-987 Cl F C2H5C2H5H CH3B-988 Cl F C2H5CH2C6H5H CH3B-989 Cl F CH2C6H5CH2C6H5H CH3B-990 Cl F -CH2-CH2- H CH3B-991 Cl F H H H C2H5B-992 Cl F H CH3H C2H5B-993 Cl F H C2H5H C2H5B-994 Cl F H CH2C6H5H C2H5B-995 Cl F CH3CH3H C2H5B-996 Cl F CH3C2H5H C2H5B-997 Cl F CH3CH2C6H5H C2H5B-998 Cl F C2H5C2H5H C2H5B-999 Cl F C2H5CH2C6H5H C2H5

[0803]

[0804] 250444W001

[0805] 70

[0806] No. X1X2R5R6R7R8B-1000 Cl F CH2C6H5CH2C6H5H C2H5B-1001 Cl F -CH2-CH2- H C2H5B-1002 Cl F H H H CH2C6H5B-1003 Cl F H CH3H CH2C6H5B-1004 Cl F H C2H5H CH2C6H5B-1005 Cl F H CH2C6H5H CH2C6H5B-1006 Cl F CH3CH3H CH2C6H5B-1007 Cl F CH3C2H5H CH2C6H5B-1008 Cl F CH3CH2C6H5H CH2C6H5B-1009 Cl F C2H5C2H5H CH2C6H5B-1010 Cl F C2H5CH2C6H5H CH2C6H5B-1011 Cl F CH2C6H5CH2C6H5H CH2C6H5B-1012 Cl F -CH2-CH2- H CH2C6H5B-1013 Cl F H H CH3CH3B-1014 Cl F H CH3CH3CH3B-1015 Cl F H C2H5CH3CH3B-1016 Cl F H CH2C6H5CH3CH3B-1017 Cl F CH3CH3CH3CH3B-1018 Cl F CH3C2H5CH3CH3B-1019 Cl F CH3CH2C6H5CH3CH3B-1020 Cl F C2H5C2H5CH3CH3B-1021 Cl F C2H5CH2C6H5CH3CH3B-1022 Cl F CH2C6H5CH2C6H5CH3CH3B-1023 Cl F -CH2-CH2- CH3CH3B-1024 Cl F H H CH3C2H5B-1025 Cl F H CH3CH3C2H5B-1026 Cl F H C2H5CH3C2H5

[0807]

[0808] 250444W001

[0809] 71

[0810] No. X1X2R5R6R7R8B-1027 Cl F H CH2C6H5CH3C2H5B-1028 Cl F CH3CH3CH3C2H5B-1029 Cl F CH3C2H5CH3C2H5B-1030 Cl F CH3CH2C6H5CH3C2H5B-1031 Cl F C2H5C2H5CH3C2H5B-1032 Cl F C2H5CH2C6H5CH3C2H5B-1033 Cl F CH2C6H5CH2C6H5CH3C2H5B-1034 Cl F -CH2-CH2- CH3C2H5B-1035 Cl F H H CH3CH2C6H5B-1036 Cl F H CH3CH3CH2C6H5B-1037 Cl F H C2H5CH3CH2C6H5B-1038 Cl F H CH2C6H5CH3CH2C6H5B-1039 Cl F CH3CH3CH3CH2C6H5B-1040 Cl F CH3C2H5CH3CH2C6H5B-1041 Cl F CH3CH2C6H5CH3CH2C6H5B-1042 Cl F C2H5C2H5CH3CH2C6H5B-1043 Cl F C2H5CH2C6H5CH3CH2C6H5B-1044 Cl F CH2C6H5CH2C6H5CH3CH2C6H5B-1045 Cl F -CH2-CH2- CH3CH2C6H5B-1046 Cl F H H C2H5C2H5B-1047 Cl F H CH3C2H5C2H5B-1048 Cl F H C2H5C2H5C2H5B-1049 Cl F H CH2C6H5C2H5C2H5B-1050 Cl F CH3CH3C2H5C2H5B-1051 Cl F CH3C2H5C2H5C2H5B-1052 Cl F CH3CH2C6H5C2H5C2H5B-1053 Cl F C2H5C2H5C2H5C2H5

[0811]

[0812] 250444W001

[0813] 72

[0814] No. X1X2R5R6R7R8B-1054 Cl F C2H5CH2C6H5C2H5C2H5B-1055 Cl F CH2C6H5CH2C6H5C2H5C2H5B-1056 Cl F -CH2-CH2- C2H5C2H5B-1057 Cl F H H C2H5CH2C6H5B-1058 Cl F H CH3C2H5CH2C6H5B-1059 Cl F H C2H5C2H5CH2C6H5B-1060 Cl F H CH2C6H5C2H5CH2C6H5B-1061 Cl F CH3CH3C2H5CH2C6H5B-1062 Cl F CH3C2H5C2H5CH2C6H5B-1063 Cl F CH3CH2C6H5C2H5CH2C6H5B-1064 Cl F C2H5C2H5C2H5CH2C6H5B-1065 Cl F C2H5CH2C6H5C2H5CH2C6H5B-1066 Cl F CH2C6H5CH2C6H5C2H5CH2C6H5B-1067 Cl F -CH2-CH2- C2H5CH2C6H5B-1068 Cl F H H CH2C6H5CH2C6H5B-1069 Cl F H CH3CH2C6H5CH2C6H5B-1070 Cl F H C2H5CH2C6H5CH2C6H5B-1071 Cl F H CH2C6H5CH2C6H5CH2C6H5B-1072 Cl F CH3CH3CH2C6H5CH2C6H5B-1073 Cl F CH3C2H5CH2C6H5CH2C6H5B-1074 Cl F CH3CH2C6H5CH2C6H5CH2C6H5B-1075 Cl F C2H5C2H5CH2C6H5CH2C6H5B-1076 Cl F C2H5CH2C6H5CH2C6H5CH2C6H5B-1077 Cl F CH2C6H5CH2C6H5CH2C6H5CH2C6H5B-1078 Cl F -CH2-CH2- CH2C6H5CH2C6H5B-1079 Cl F H H -CH2-CH2- B-1080 Cl F H CH3-CH2-CH2-

[0815]

[0816] 250444W001

[0817] 73

[0818] No. X1X2R5R6R7R8

[0819] B-1081 Cl F H C2H5-CH2-CH2- B-1082 Cl F H CH2C6H5-CH2-CH2- B-1083 Cl F CH3CH3-CH2-CH2- B-1084 Cl F CH3C2H5-CH2-CH2- B-1085 Cl F CH3CH2C6H5-CH2-CH2- B-1086 Cl F C2H5C2H5-CH2-CH2- B-1087 Cl F C2H5CH2C6H5-CH2-CH2- B-1088 Cl F CH2C6H5CH2C6H5-CH2-CH2- B-1089 Cl F -CH2-CH2- -CH2-CH2-

[0820]

[0821] In particular with a view to their use, according to one embodiment, preference is given to the compounds of the compounds LA-1, I.A-2, I.A-3, I.A-4, I.A-5, I.A-6, that are compiled in the Tables 1a to 6a. Each of the groups mentioned for a substituent in the tables is furthermore per se, independently of the combination in which it is mentioned, a particularly preferred aspect of the substituent in question.

[0822] I.B-1 I.B-2

[0823] I.B-6

[0824]

[0825] Table 1b Compounds of the formula I.B-1, I.B-2, I.B-3, I.B-4, I.B-5, I.B-6, in which R2or R3is CH3and the meaning of the combination of X1, X2, R5and R6for each individual compound250444W001

[0826] 74

[0827] corresponds in each case to one line of Table C (compounds I.B-1.1 b.C-1 to I.B-1.1b. C-99, I.B-2.1b. C-1 to I.B-2.1b. C-99, I.B-3.1 b.C-1 to I.B-3.1b.C-99, I.B-4.1b.C-1 to I.B-4.1b.C-99, I.B-5.1b. C-1 to I.B-5.1b. C-99, I.B-6.1b.C-1 to I.B-6.1b.C-99).

[0828] Table 2b Compounds of the formula I.B-1, I.B-2, I.B-3, I.B-4, I.B-5, I.B-6, in which R2or R3is CH3and the meaning of the combination of X1, X2, R5and R6for each individual compound corresponds in each case to one line of Table C (compounds I.B-1.2b. C-1 to I.B-1.2b. C-99, I.B-2.2b. C-1 to I.B-2.2b. C-99, I.B-3.2b.C-1 to I.B-3.2b.C-99, I.B-4.2b.C-1 to I.B-4.2b.C-99, I.B-5.2b. C-1 to I.B-5.2b. C-99, I.B-6.2b.C-1 to I.B-6.2b.C-99).

[0829] Table 3b Compounds of the formula I.B-1, I.B-2, I.B-3, I.B-4, I.B-5, I.B-6, in which R2or R3is Cl and the meaning of the combination of X1, X2, R5and R6for each individual compound corresponds in each case to one line of Table C (compounds I.B-1.3b. C-1 to I.B-1.3b. C-99, I.B-2.3b. C-1 to I.B-2.3b. C-99, I.B-3.3b.C-1 to I.B-3.3b.C-99, I.B-4.3b.C-1 to I.B-4.3b.C-99, I.B-5.3b. C-1 to I.B-5.3b. C-99, I.B-6.3b.C-1 to I.B-6.3b.C-99).

[0830] Table 4b Compounds of the formula I.B-1, I.B-2, I.B-3, I.B-4, I.B-5, I.B-6, in which R2or R3is Br and the meaning of the combination of X1, X2, R5and R6for each individual compound corresponds in each case to one line of Table C (compounds I.B-1.4b. C-1 to I.B-1.4b. C-99, I.B-2.4b. C-1 to I.B-2.4b. C-99, I.B-3.4b.C-1 to I.B-3.4b.C-99, I.B-4.4b.C-1 to I.B-4.4b.C-99, I.B-5.4b. C-1 to I.B-5.4b. C-99, I.B-6.4b.C-1 to I.B-6.4b.C-99).

[0831] Table 5b Compounds of the formula I.B-1, I.B-2, I.B-3, I.B-4, I.B-5, I.B-6, in which R2or R3is CN and the meaning of the combination of X1, X2, R5and R6for each individual compound corresponds in each case to one line of Table C (compounds I.B-1.5b. C-1 to I.B-1.5b. C-99, I.B-2.5b. C-1 to I.B-2.5b. C-99, I.B-3.5b.C-1 to I.B-3.5b.C-99, I.B-4.5b.C-1 to I.B-4.5b.C-99, I.B-5.5b. C-1 to I.B-5.5b. C-99, I.B-6.5b.C-1 to I.B-6.5b.C-99).

[0832] Table 6b Compounds of the formula I.B-1, I.B-2, I.B-3, I.B-4, I.B-5, I.B-6, in which R2or R3is CHF2and the meaning of the combination of X1, X2, R5and R6for each individual compound corresponds in each case to one line of Table C (compounds I.B-1.6b. C-1 to I.B-1.6b. C-99, I.B-2.6b. C-1 to I.B-2.6b. C-99, I.B-3.6b.C-1 to I.B-3.6b.C-99, I.B-4.6b.C-1 to I.B-4.6b.C-99, I.B-5.6b. C-1 to I.B-5.6b. C-99, I.B-6.6b.C-1 to I.B-6.6b.C-99).

[0833] Table 7b Compounds of the formula I.B-1, I.B-2, I.B-3, I.B-4, I.B-5, I.B-6, in which R2or R3is CH3and R9is H and the meaning of the combination of X1, X2, R5and R6for each individual compound corresponds in each case to one line of Table C (compounds I.B-1.7b. C-1 to I.B-1.7b. C-99, I.B-2.7b. C-1 to I.B-2.7b.C-99, I.B-3.7b.C-1 to I.B-3.7b.C-99, I.B-4.7b.C-1 to I.B-4.7b. C-99, I.B-5.7b. C-1 to I.B-5.7b.C-99, I.B-6.7b.C-1 to I.B-6.7b.C-99).

[0834] Table 8b Compounds of the formula I.B-1, I.B-2, I.B-3, I.B-4, I.B-5, I.B-6, in which R2or R3is CH3and R9is H and the meaning of the combination of X1, X2, R5and R6for each individual compound corresponds in each case to one line of Table C (compounds I.B-1.8b. C-1 to I.B-1.8b. C-99, I.B-2.8b. C-1 to I.B-2.8b.C-99, I.B-3.8b.C-1 to I.B-3.8b.C-99, I.B-4.8b.C-1 to I.B-4.8b. C-99, I.B-5.8b. C-1 to I.B-5.8b.C-99, I.B-6.8b.C-1 to I.B-6.8b.C-99).

[0835] Table 9b Compounds of the formula I.B-1, I.B-2, I.B-3, I.B-4, I.B-5, I.B-6, in which R2or R3is Cl and R9is H and the meaning of the combination of X1, X2, R5and R6for each individual compound corresponds in each case to one line of Table C (compounds I.B-1.9b. C-1 to I.B-250444W001

[0836] 75

[0837] 1.9b.C-99, I.B-2.9b. C-1 to I.B-2.9b.C-99, I.B-3.9b.C-1 to I.B-3.9b.C-99, I.B-4.9b.C-1 to I.B-4.9b.C-99, I.B-5.9b. C-1 to I.B-5.9b.C-99, I.B-6.9b.C-1 to I.B-6.9b.C-99).

[0838] Table 10b Compounds of the formula I.B-1, I.B-2, I.B-3, I.B-4, I.B-5, I.B-6, in which R2or R3is Br and R9is H and the meaning of the combination of X1, X2, R5and R6for each individual compound corresponds in each case to one line of Table C (compounds I.B-1.10b. C-1 to I.B-1.10b.C-99, LB-2.10b.C-1 to LB-2.10b.C-99, LB-3.10b.C-1 to LB-3.10b.C-99, LB-4.10b.C-1 to LB-4.10b.C-99, LB-5.10b.C-1 to LB-5.10b.C-99, LB-6.10b.C-1 to LB-6.10b.C-99).

[0839] Table 11b Compounds of the formula I.B-1, I.B-2, I.B-3, I.B-4, I.B-5, I.B-6, in which R2or R3is CN and R9is H and the meaning of the combination of X1, X2, R5and R6for each individual compound corresponds in each case to one line of Table C (compounds I.B-1.11b. C-1 to I.B-1.11b.C-99, LB-2.11b.C-1 to I.B-2.11b.C-99, I.B-3.11b.C-1 to I.B-3.11b.C-99, I.B-4.11b.C-1 to LB-4.11b.C-99, LB-5.11b.C-1 to I.B-5.11b.C-99, I.B-6.11b.C-1 to I.B-6.11b.C-99).

[0840] Table 12b Compounds of the formula I.B-1, I.B-2, I.B-3, I.B-4, I.B-5, I.B-6, in which R2or R3is CHF2and R9is H and the meaning of the combination of X1, X2, R5and R6for each individual compound corresponds in each case to one line of Table C (compounds I.B-1.12b. C-1 to I.B-1.12b.C-99, LB-2.12b.C-1 to LB-2.12b.C-99, LB-3.12b.C-1 to LB-3.12b.C-99, LB-4.12b.C-1 to LB-4.12b.C-99, LB-5.12b.C-1 to LB-5.12b.C-99, LB-6.12b.C-1 to LB-6.12b.C-99).

[0841] Table 13b Compounds of the formula I.B-1, I.B-2, I.B-3, I.B-4, I.B-5, I.B-6, in which R2or R3is CH3and R9is CH3and the meaning of the combination of X1, X2, R5and R6for each individual compound corresponds in each case to one line of Table C (compounds I.B-1.13b. C-1 to I.B-1.13b.C-99, LB-2.13b.C-1 to LB-2.13b.C-99, LB-3.13b.C-1 to LB-3.13b.C-99, LB-4.13b.C-1 to LB-4.13b.C-99, LB-5.13b.C-1 to LB-5.13b.C-99, LB-6.13b.C-1 to LB-6.13b.C-99).

[0842] Table 14b Compounds of the formula I.B-1, I.B-2, I.B-3, I.B-4, I.B-5, I.B-6, in which R2or R3is CH3and R9is CH3and the meaning of the combination of X1, X2, R5and R6for each individual compound corresponds in each case to one line of Table C (compounds I.B-1.14b. C-1 to I.B-1.14b.C-99, LB-2.14b.C-1 to LB-2.14b.C-99, LB-3.14b.C-1 to LB-3.14b.C-99, LB-4.14b.C-1 to LB-4.14b.C-99, LB-5.14b.C-1 to LB-5.14b.C-99, LB-6.14b.C-1 to LB-6.14b.C-99).

[0843] Table 15b Compounds of the formula I.B-1, I.B-2, I.B-3, I.B-4, I.B-5, I.B-6, in which R2or R3is Cl and R9is CH3and the meaning of the combination of X1, X2, R5and R6for each individual compound corresponds in each case to one line of Table C (compounds I.B-1.15b. C-1 to I.B-1.15b.C-99, LB-2.15b.C-1 to LB-2.15b.C-99, LB-3.15b.C-1 to LB-3.15b.C-99, LB-4.15b.C-1 to LB-4.15b.C-99, LB-5.15b.C-1 to LB-5.15b.C-99, LB-6.15b.C-1 to LB-6.15b.C-99).

[0844] Table 16b Compounds of the formula I.B-1, I.B-2, I.B-3, I.B-4, I.B-5, I.B-6, in which R2or R3is Br and R9is CH3and the meaning of the combination of X1, X2, R5and R6for each individual compound corresponds in each case to one line of Table C (compounds I.B-1.16b. C-1 to I.B-1.16b.C-99, LB-2.16b.C-1 to LB-2.16b.C-99, LB-3.16b.C-1 to LB-3.16b.C-99, LB-4.16b.C-1 to LB-4.16b.C-99, LB-5.16b.C-1 to LB-5.16b.C-99, LB-6.16b.C-1 to LB-6.16b.C-99).

[0845] Table 17b Compounds of the formula I.B-1, I.B-2, I.B-3, I.B-4, I.B-5, I.B-6, in which R2or R3is CN and R9is CH3and the meaning of the combination of X1, X2, R5and R6for each individual compound corresponds in each case to one line of Table C (compounds I.B-1.17b. C-1 to I.B-1.17b.C-99, LB-2.17b.C-1 to LB-2.17b.C-99, LB-3.17b.C-1 to LB-3.17b.C-99, LB-4.17b.C-1 to250444W001

[0846] 76

[0847] LB-4.17b.C-99, LB-5.17b.C-1 to LB-5.17b.C-99, LB-6.17b.C-1 to LB-6.17b.C-99).

[0848] Table 18b Compounds of the formula I.B-1, I.B-2, I.B-3, I.B-4, I.B-5, I.B-6, in which R2or R3is CHF2and R9is CH3and the meaning of the combination of X1, X2, R5and R6for each individual compound corresponds in each case to one line of Table C (compounds I.B-1.18b. C-1 to I.B-1.18b.C-99, LB-2.18b.C-1 to LB-2.18b.C-99, LB-3.18b.C-1 to LB-3.18b.C-99, LB-4.18b.C-1 to LB-4.18b.C-99, LB-5.18b.C-1 to LB-5.18b.C-99, LB-6.18b.C-1 to LB-6.18b.C-99).

[0849] Table C

[0850] No. X1X2R5R6

[0851] C-1 H H H H

[0852] C-2 H H H CH3

[0853] C-3 H H H C2H5

[0854] C-4 H H H CH2C6H5C-5 H H CH3CH3

[0855] C-6 H H CH3C2H5

[0856] C-7 H H CH3CH2C6H5C-8 H H C2H5C2H5

[0857] C-9 H H C2H5CH2C6H5C-10 H H CH2C6H5CH2C6H5C-11 H H -CH2-CH2- C-12 H F H H

[0858] C-13 H F H CH3

[0859] C-14 H F H C2H5

[0860] C-15 H F H CH2C6H5C-16 H F CH3CH3

[0861] C-17 H F CH3C2H5

[0862] C-18 H F CH3CH2C6H5C-19 H F C2H5C2H5

[0863] C-20 H F C2H5CH2C6H5C-21 H F CH2C6H5CH2C6H5C-22 H F -CH2-CH2-

[0864]

[0865] 250444W001

[0866] 77

[0867] No. X1X2R5R6

[0868] C-23 F H H H

[0869] C-24 F H H CH3

[0870] C-25 F H H C2H5C-26 F H H CH2C6H5C-27 F H CH3CH3

[0871] C-28 F H CH3C2H5C-29 F H CH3CH2C6H5C-30 F H C2H5C2H5C-31 F H C2H5CH2C6H5C-32 F H CH2C6H5CH2C6H5C-33 F H -CH2-CH2- C-34 F F H H

[0872] C-35 F F H CH3

[0873] C-36 F F H C2H5C-37 F F H CH2C6H5C-38 F F CH3CH3

[0874] C-39 F F CH3C2H5C-40 F F CH3CH2C6H5C-41 F F C2H5C2H5C-42 F F C2H5CH2C6H5C-43 F F CH2C6H5CH2C6H5C-44 F F -CH2-CH2- C-45 H Cl H H

[0875] C-46 H Cl H CH3

[0876] C-47 H Cl H C2H5C-48 H Cl H CH2C6H5C-49 H Cl CH3CH3

[0877]

[0878] 250444W001

[0879] 78

[0880] No. X1X2R5R6

[0881] C-50 H Cl CH3C2H5C-51 H Cl CH3CH2C6H5C-52 H Cl C2H5C2H5C-53 H Cl C2H5CH2C6H5C-54 H Cl CH2C6H5CH2C6H5C-55 H Cl -CH2-CH2- C-56 Cl H H H

[0882] C-57 Cl H H CH3

[0883] C-58 Cl H H C2H5C-59 Cl H H CH2C6H5C-60 Cl H CH3CH3

[0884] C-61 Cl H CH3C2H5C-62 Cl H CH3CH2C6H5C-63 Cl H C2H5C2H5C-64 Cl H C2H5CH2C6H5C-65 Cl H CH2C6H5CH2C6H5C-66 Cl H -CH2-CH2- C-67 Cl Cl H H

[0885] C-68 Cl Cl H CH3

[0886] C-69 Cl Cl H C2H5C-70 Cl Cl H CH2C6H5C-71 Cl Cl CH3CH3

[0887] C-72 Cl Cl CH3C2H5C-73 Cl Cl CH3CH2C6H5C-74 Cl Cl C2H5C2H5C-75 Cl Cl C2H5CH2C6H5C-76 Cl Cl CH2C6H5CH2C6H5

[0888]

[0889] 250444W001

[0890] 79

[0891] No. X1X2R5R6

[0892] C-77 Cl Cl -CH2-CH2- C-78 Cl F H H

[0893] C-79 Cl F H CH3

[0894] C-80 Cl F H C2H5

[0895] C-81 Cl F H CH2C6H5C-82 Cl F CH3CH3

[0896] C-83 Cl F CH3C2H5

[0897] C-84 Cl F CH3CH2C6H5C-85 Cl F C2H5C2H5

[0898] C-86 Cl F C2H5CH2C6H5C-87 Cl F CH2C6H5CH2C6H5C-88 Cl F -CH2-CH2- C-89 F Cl H H

[0899] C-90 F Cl H CH3

[0900] C-91 F Cl H C2H5

[0901] C-92 F Cl H CH2C6H5C-93 F Cl CH3CH3

[0902] C-94 F Cl CH3C2H5

[0903] C-95 F Cl CH3CH2C6H5C-96 F Cl C2H5C2H5

[0904] C-97 F Cl C2H5CH2C6H5C-98 F Cl CH2C6H5CH2C6H5C-99 F Cl -CH2-CH2-

[0905]

[0906] Compounds of the present invention can be made as shown in the following schemes, in which, unless otherwise stated, the definition of each variable is as defined above for a compound of formula I. The compounds of the formula I can be prepared according to methods or in analogy to methods that are described in the prior art. The synthesis takes advantage of starting materials that are commercially available or may be prepared according to conventional250444W001

[0907] 80

[0908] procedures starting from readily available compounds. Enantiopure compounds may be obtained by racemic synthesis and subsequent seaparation of the stereoisomers using chiral column chromatography, e.g. via chiral HPLC, LC / MS and / or SFC separation.

[0909] Compounds I can be prepared via a palladium catalyzed Suzuki coupling reaction between a boronic acid derivative represented by formula (3) and an imidoyl halide derivative represented by formula (2) using a palladium complex in an organic solvent. It is preferred to conduct the reaction at elevated temperature, preferably between 60 and 160 °C, and using 1-3 equivalents of boronic acid derivative represented by formula (3) per 1 imidoyl halide derivative (2), as described in W02009119089A.

[0910]

[0911] An imidoyl compound represented by formula (2) can be prepared by a method in which a cyclic amide represented by formula (4) is reacting in the presence of a suitable halogenating agent such as triphenylphosphine and a carbon tetrahalide, triphenylphosphine dichloride, phosgene, oxalyl chloride orthionyl chloride as described in US 2011 / 0136782 A1.

[0912]

[0913] lfZ = O, S and o = 1

[0914] A compound represented by formula (4) can be prepared by deriving from a cyclic acetophenone derivative represented by formula (6) to an oxime by a Schmidt reaction and then carrying out a Beckmann rearrangement. Various variations have been reported for both reactions. The Schmidt reaction can be carried out by, for example, reacting a ketone in sodium azide and a strong acid, such as concentrated hydrochloric acid, sulfuric acid, trifluoroacetic acid or methane sulfonic acid, and in the absence of a solvent or in a solvent such as acetonitrile, chloroform or methylene chloride. In the Beckmann rearrangement, an oxime of a carbonyl compound is reacted with polyphosphoric acid or a trimethylsilyl ester thereof or reacting at a high temperature with a Lewis acid such as aluminum triiodide or iron (III) chloride-impregnated montmorillonite or with thionyl chloride in the absence of solvent or in the presence of a solvent such as acetonitrile. In addition, it can also be prepared by forming a mesylate or tosylate of an oxime followed by treating with a base such as aqueous sodium hydroxide250444W001

[0915] 81

[0916] solution or treating with a Lewis acid such as diethyl aluminum chloride, as described in Heterocycles (1994), 38(2), 305- 15 18; US 2011 / 0136782 A1.

[0917]

[0918] Alternatively, the compound represented by formula (4) can be prepared in a one pot by copper(ll)-catalyzed Beckmann rearrangement of ketones (6) under mild reaction conditions using hydroxylamine-O-sulfonic acid as aminating agent, as described in Synthesis 2019, 51(19), 3709-3714.

[0919] The oxime (5) can be prepared using a known method by reacting with hydroxylamine hydrochloride in a solvent such as ethanol followed by adding a base such as pyridine or sodium acetate or aqueous sodium hydroxide solution as necessary at a temperature up to the boiling point of the solvent, as described in Bioorganic & Medicinal Chemistry (2008), 16(11), 6124-6130; Heterocyclic Communications (1998), 4(6), 547-557.

[0920]

[0921] The cyclic acetophenone derivatives represented by formula (6) are commercially available or can be accessed starting from 2-hydroxyacetophenone via a classical ring closure reaction using the corresponding ketone in the presence of pyrrolidine, as described in Bioorganic & Medicinal Chemistry (2008), 16(11), 6124-6130; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1995).

[0922] lf Z = N(R7) and o = 0

[0923] For example, the formation of a compound (7) from a compound of formula (8) is suitably conducted by alkylation or acylation in the presence of a base such as potassium or sodium lower alkoxide or hydride. Di-lower alkyl sulfates can also be used to effect said alkylation or acylation, as described in US 3,625,959.

[0924] The cyclic compounds of the formula (8) can be prepared from keto amine compound (9) by reaction with ketone or aldehyde of the formula (10) in the presence of ammonium acetate. In some cases, the presence of an acid like p-toluenesulfonic acid (p-TsOH), pyridinium p-toluenesulfonate, sulfuric acid or acetic acid improves the yields (for precedents see for example in Chemistry Select (2018), 3(32), 9388-9392 and Organic & Biomolecular Chemistry (2003), 1(2), 367-372).250444W001

[0925]

[0926] Compounds of the (9) are commercially available or can be accessed followed the general pathway outlined in following scheme by oxidation of the amino alcohol (11) using for example manganese dioxide, as described in Inorganica Chimica Acta (2012), 382, 72-78, W02000038618, CN107879989 A, Chinese Science Bulletin (2010), 55(25), 2817-2819.

[0927] Compounds of the formula (11) can be accessed via catalytic hydrogenation of the respective nitro alcohol (12) using RANEYO-nickel, as described in W02000038618, Inorganica Chimica Acta (2012), 382, 72-78.

[0928] The 2-nitro alcohol (12) can be prepared from (14) by phenyl magnesium bromide-mediated iodine-magnesium exchange in ortho position to NO2as described by Knochel and coworkers (Angew. Chem., Int. Ed., 2002, 41, 1610), and subsequent addition to commercially available benzaldehyde derivative (13).

[0929]

[0930] Compounds of the formula (7), wherein R7is alkoxy can be prepared from (12) via following synthetic route, which is characterized by a selective catalytic hydrogenation of the nitro alcohol (12) to the corresponding / V-arylhydroxylamines (19) using passivated RANEYO-nickel, which was treated by a combined liquid of aqueous ammonia and DMSO, as described in RSC Advances (2020), 28585-28594 or using platinum on carbon (type F 103 RS / W from Degussa), as described in IN1996CH00112.250444W001

[0931]

[0932] Compounds of the formula (18) can be prepared by oxidation of the hydroxyl-amine alcohol (19) using for example manganese dioxide, as described in Inorganica Chimica Acta (2012), 382, 72-78 and W02000038618.

[0933] The protected hydroxyl amine (17) can be prepared by methods well known in the literature for amino protecting groups as discussed in Theodora W. Greene's book "Protective Groups in Organic Synthesis", like N-Boc using di-tert. butyldicarbonate in an appropriate solvent like DMSO.

[0934] Compounds (17) can be alkylated using standard bases like LDA, NaH, or NaHMDS to deprotonate the hydroxyl amine followed by addition of an alkylating agent with an appropriate leaving group like halide, mesylate, ortriflate in an appropriate solvent to provide compounds (16) (for precedents see for example CN207973751).

[0935] The N-Boc protecting group can be removed by any number of methods well known in the literature like TFA in methylene chloride to give the compound (15) (for precedents see for example W02000038618). Finally, compounds (7), wherein R7 is alkoxy can be prepared from (15) by treating with NH4OAc as described in Chemistry Select (2018), 3(32), 9388-9392 and Organic & Biomolecular Chemistry (2003), 1(2), 367-372.

[0936] lf Z = N(R7) and o = 1

[0937] For example, compounds (20) can be prepared via alkylation or acylation of benzodiazepines represented by the formula (21) with a range of alkyl halides and acyl chlorides, which can be effected by deprotonation of the benzodiazepines (21) with a range of organic or inorganic bases, such as potassium te / Y-butoxide or sodium hydride. The reaction is preferentially performed at 0°C to room temperature, with in some cases sluggish reactions being carried out at temperatures up to 60°C, and using 1-5 equivalents of base and 1-3 equivalents of alkylating / acylating reagent, as described in Chem. Eur. J. (2016), 22, 10607-10613, 15 CN114349714 A, W02008 / 118141 A2, or US2012 / 184732 A1.250444W001

[0938] 84

[0939] The benzodiazepine compounds represented by the formula (21) can be prepared by reacting a range of diamines (or HCI salts thereof) represented by the formula (23) with aryl ketones (22) substituted with at least 1 halogen (represented by X, preferentially F) in the presence of a base. The reaction is preferentially performed from rt to 120 °C, with 1-6 equivalents of base and 1 to 1.5 equivalents of diamine, analogous to a method described in WO2016 / 87370 A1 , Org. Biomol. Chem. (2014), 12, 6895-6900, WO2006 / 44753 A2, Heterocycles (1994), 38, 125-134.

[0940] R2R3R4R!AP<.RH2N NH223

[0941]

[0942] Aryl ketones (22) are either commercially available or can be prepared by oxidation of the aryl alcohol (23), using for example manganese dioxide, as described in Inorganica Chimica Acta (2012), 382, 72- 78, WO 2000 / 038618, CN107879989 A, or Chinese Science Bulletin 2010, 55(25), 2817-2819.

[0943] MnO2

[0944]

[0945] 23 21

[0946] Aryl alcohols (23) can be prepared by isopropyl magnesium chloride-mediated bromine / iodine magnesium exchange of (25), and subsequent addition to commercially available aldehydes represented by the general formula (24). The reaction is preferentially carried out at 0°C, with an equimolar ratio of / PrMgCI and aryl halides (25), the intermediate of which is employed in a ratio of 1.2-1.3:1 with respect to aldehydes (24), as described in US2010 / 41698 A1, Org. Lett.

[0947] (2018), 20, 138-141, WO2014 / 102233 A1, or US2016 / 83401 A1.

[0948] X

[0949]

[0950] 24 23

[0951] Alternatively, the scaffold represented by formula (20) may also be accessed by reacting aryl ketones (21) with partially protected diamines (27) in the presence of organic or inorganic bases at temperatures up to 200 °C under microwave irradiation, as described in US2006 / 178386 A1 , Bioorganic & Medicinal Chemistry Letters (2021), 35,127813, Chem. Sci. (2021), 12, 4519-4525, or J. Org. Chem. (2005), 70, 8924-8931. The resulting product (26) may then be further reacted at 0°C in a 1.5:7 mixture of TFA:DCM to lead to the condensed product represented by250444W001

[0952] 85

[0953] formula (21), as described in US2006 / 3995, J. Bioorg. Med. Chem. Lett. (2007), 17, 2527-2530, W02022 / 99011 A1, Org Lett. (2012), 14, 5916-5919, or J. Med. Chem. (2016), 59, 10661-10675. Alkylation / acylation as to obtain the compounds (20) can then be carried out as described above.

[0954] 21 26

[0955]

[0956] 20 21

[0957] The compounds I and the compositions thereof, respectively, are suitable as fungicides effective against a broad spectrum of phytopathogenic fungi, including soil-borne fungi, in particular from Plasmodiophoromycetes, Peronosporomycetes (syn. Oomycetes), Chytridio-mycetes, Zygomycetes, Ascomycetes, Basidiomycetes, and Deuteromycetes (syn. Fungi imperfecti). They can be used in crop protection as foliar fungicides, fungicides for seed dressing, and soil fungicides.

[0958] The compounds I and the compositions thereof are preferably useful in the control of phytopathogenic fungi on various cultivated plants, such as cereals (e.g. wheat, rye, barley, triticale, oats, millet, corn [maize] or rice); beets (e.g. sugar or fodder beet); fruits, (e.g. pomes: apples, pears, etc.); stone fruits (e.g. plums, peaches, almonds, cherries), or soft fruits, also called berries (e.g. strawberries, raspberries, blackberries, gooseberries, etc.); leguminous plants (e.g. lentils, peas, alfalfa, or soybeans); oil plants (e.g. oilseed rape, mustard, olives, sunflowers, coconut, cocoa beans, castor oil plants, oil palms, ground nuts, or soybeans); cucurbits (e.g. squashes, cucumber, or melons); fiber plants (e.g. cotton, flax, hemp, or jute); citrus fruits (e.g. oranges, lemons, grapefruits, or mandarins); vegetables (e.g. spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, cucurbits, or paprika); lauraceous plants (e.g. avocados, cinnamon, or camphor); energy and raw material plants (e.g. corn [maize], soybean, oilseed 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, (e.g. flowers, shrubs, broadleaved trees, or evergreens (conifers, eucalypts, etc.)); on the plant propagation material, such250444W001

[0959] 86

[0960] as seeds; and on the crop material of these plants.

[0961] More preferably, compounds I and compositions thereof, respectively are used for controlling fungi on field crops, such as potatoes, sugar beets, tobacco, wheat, rye, barley, oats, rice, corn [maize], cotton, soybeans, oilseed rape, legumes, sunflowers, coffee or sugar cane; fruits; vines; ornamentals; or vegetables, such as cucumbers, tomatoes, beans or squashes.

[0962] The term "plant propagation material" is to be understood to denote all the generative parts of the plant, such as seeds; and vegetative plant materials, 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 to be transplanted after germination or after emergence from soil.

[0963] Preferably, treatment of plant propagation materials with compounds I and compositions thereof, respectively, is used for controlling fungi on cereals, such as wheat, rye, barley and oats; rice, corn, cotton and soybeans.

[0964] According to the invention all of the above cultivated plants are understood to comprise all species, subspecies, variants, varieties and / or hybrids which belong to the respective cultivated plants, including but not limited to winter and spring varieties, in particular in cereals such as wheat and barley, as well as oilseed rape, e.g. winter wheat, spring wheat, winter barley etc, further including dwarf, semi-dwarf and full-dwarf varieties and / or hybrids with reduced height and thicker and shorter stems, e.g. short stature corn (also called ‘smart corn’), semi-dwarf wheat and dwarf rice.

[0965] Corn (Zea mays) is also known as Indian corn or maize which comprises all kinds of corn such as field corn and sweet corn. According to the invention all maize or corn subspecies and / or varieties are comprised, in particular flour corn (Zea mays var. amylacea), popcorn (Zea mays var. everta), dent corn (Zea mays var. indentata), flint corn (Zea mays var. indurata), sweet corn (Zea mays var. saccharata and var. rugosa), waxy corn (Zea mays var. ceratina), amylomaize (high amylose Zea mays varieties), pod corn or wild maize (Zea mays var. tunicata) and striped maize (Zea mays var. japonica).

[0966] Most soybean cultivars are classifiable into indeterminate and determinate growth habit, whereas Glycine soja, the wild progenitor of soybean, is indeterminate (PNAS 2010, 107 (19) 8563-8568). The indeterminate growth habit (Maturity Group, MG 00 to MG 4.9) is characterized by a continuation of vegetative growth after flowering begins whereas determinate soybean varieties (MG 5 to MG 8) characteristically have finished most of their vegetative growth when flowering begins. According to the invention all soybean cultivars or varieties are comprised, in particular indeterminate and determinate cultivars or varieties.

[0967] The term "cultivated plants" is to be understood as including plants which have been modified by mutagenesis or genetic engineering to provide a new trait to a plant or to modify an already present trait. Mutagenesis includes random mutagenesis using X-rays or mutagenic chemicals, but also targeted mutagenesis to create mutations at a specific locus of a plant genome.

[0968] Targeted mutagenesis frequently uses oligonucleotides or proteins like CRISPR / Cas, zinc-finger nucleases, TALENs or meganucleases. Genetic engineering usually uses recombinant DNA techniques to create modifications in a plant genome which under natural circumstances cannot readily be obtained by cross breeding, mutagenesis or natural recombination. Typically,250444W001

[0969] 87

[0970] one or more genes are integrated into the genome of a plant to add a trait or improve or modify a trait. These integrated genes are also referred to as transgenes, while plant comprising such transgenes are referred to as transgenic plants. The process of plant transformation usually produces several transformation events, which differ in the genomic locus in which a transgene has been integrated. Plants comprising a specific transgene on a specific genomic locus are usually described as comprising a specific “event”, which is referred to by a specific event name. Traits which have been introduced in plants or have been modified include herbicide tolerance, insect resistance, increased yield and tolerance to abiotic conditions, like drought. Herbicide tolerance has been created by using mutagenesis and genetic engineering. Plants which have been rendered tolerant to acetolactate synthase (ALS) inhibitor herbicides by mutagenesis and breeding are e.g. available under the name Clearfield®. Herbicide tolerance to glyphosate, glufosinate, 2,4-D, dicamba, oxynil herbicides, like bromoxynil and ioxynil, sulfonylurea herbicides, ALS inhibitors and 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors, like isoxaflutole and mesotrione, has been created via the use of transgenes.

[0971] Transgenes to provide herbicide tolerance traits comprise: for tolerance to glyphosate: cp4 epsps, epsps grg23ace5, mepsps, 2mepsps, gat4601, gat4621, goxv247; for tolerance to glufosinate: pat and bar, for tolerance to 2,4-D: aad-1, aad-12; for tolerance to dicamba: dmo; for tolerance to oxynil herbicies: bxn; for tolerance to sulfonylurea herbicides: zm-hra, csr1-2, gm-hra, S4-HrA; for tolerance to ALS inhibitors: csr1-2; and for tolerance to HPPD inhibitors: hppdPF, W336, avhppd-03.

[0972] Transgenic corn events comprising herbicide tolerance genes include, but are not limited to, DAS40278, MON801, MON802, MON809, MON810, MON832, MON87411, MON87419, MON87427, MON88017, MON89034, NK603, GA21, MZHGOJG, HCEM485, VCO-01981-5, 676, 678, 680, 33121, 4114, 59122, 98140, Bt10, Bt176, CBH-351, DBT418, DLL25, MS3, MS6, MZIR098, T25, TC1507 and TC6275. Transgenic soybean events comprising herbicide tolerance genes include, but are not limited to, GTS 40-3-2, MON87705, MON87708, MON87712, MON87769, MON89788, A2704-12, A2704-21 , A5547-127, A5547-35, DP356043, DAS44406-6, DAS68416-4, DAS-81419-2, GU262, SYHT0H2, W62, W98, FG72 and CV127. Transgenic cotton events comprising herbicide tolerance genes include, but are not limited to, 19-51a, 31707, 42317, 81910, 281-24-236, 3006-210-23, BXN10211, BXN10215, BXN10222, BXN10224, MON1445, MON1698, MON88701, MON88913, GHB119, GHB614, LLCotton25, T303-3 and T304-40. Transgenic canola events comprising herbicide tolerance genes are for example, but not excluding others, MON88302, HCR-1, HCN10, HCN28, HCN92, MS1, MS8, PHYU, PHY23, PHY35, PHY36, RF1, RF2 and RF3.

[0973] Transgenes providing insect resistance include but are not limited to, toxin genes of Bacillus spp. and synthetic variants thereof (e.g. cry1A, crylAb, cry1Ab-Ac, crylAc, cry1A.1O5, cry1F, cry1Fa2, cry2Ab2, cry2Ae, mcry3A, ecry3.1Ab, cry3Bb1, cry34Ab1, cry35Ab1, cry9C, vip3A(a), and vip3Aa20); transgenes of plant origin (e.g. coding for protease inhibitors, like CpTI and pinll); and transgenes producing double-stranded RNA (e.g. dvsnf7). Transgenic insect resistance corn events include, but are not limited to, Bt10, Bt11 , Bt176, MON801, MON802, MON809, MON810, MON863, MON87411, MON88017, MON89034, 33121, 4114, 5307, 59122, TC1507, TC6275, CBH-351, MIR162, DBT418 and MZIR098. Transgenic insect resistance soybean events include, but are not limited to, MON87701, MON87751 and DAS-81419.250444W001

[0974] 88

[0975] Transgenic cotton events comprising genes for insecticidal proteins include, but are not limited to, SGK321, MON531, MON757, MON1076, MON15985, 31707, 31803, 31807, 31808, 42317, BNLA-601, Eventl , COT67B, COT102, T303-3, T304-40, GFM Cry1A, GK12, MLS 9124, 281-24-236, 3006-210-23, GHB119 and SGK321.

[0976] Cultivated plants with increased yield have been created by using the transgene athb17 (e.g., corn event MON87403), or bbx32 (e.g. soybean event MON87712).

[0977] Cultivated plants comprising a modified oil content have been created by using the transgenes: gm-fad2-1 , Pj.D6D, Nc.Fad3, fad2-1 A and fatb1-A (e.g. soybean events 260-05, MON87705 and MON87769).

[0978] Tolerance to abiotic conditions, such as drought, has been created by using the transgene cspB (corn event MON87460) and Hahb-4 (soybean event IND-00410-5).

[0979] Traits are frequently combined by combining genes in a transformation event or by combining different events during the breeding process resulting in a cultivated plant with stacked traits. Preferred combinations of traits are combinations of herbicide tolerance traits to different groups of herbicides, combinations of insect tolerance to different kind of insects, in particular tolerance to lepidopteran and coleopteran insects, combinations of herbicide tolerance with one or several types of insect resistance, combinations of herbicide tolerance with increased yield as well as combinations of herbicide tolerance and tolerance to abiotic conditions.

[0980] Plants comprising singular or stacked traits as well as the genes and events providing these traits are well known in the art: information to the mutagenized or integrated genes and the respective events are available from websites of the “International Service for the Acquisition of Agri-biotech Applications (ISAAA)” (http: / / www.isaaa.org / gmapprovaldatabase) and the “Center for Environmental Risk Assessment (CERA)” (http: / / cera-gmc.org / GMCropDatabase). Further information can be found for canola events MS1, MS8, RF3, GT73, MON88302, KK179 in W001 / 031042, W001 / 041558, W001 / 041558, W002 / 036831, WO11 / 153186, WO13 / 003558; for cotton events MON1445, MON15985, MON531 (MON15985), LLCotton25, MON88913, COT102, 281-24-236, 3006-210-23, COT67B, GHB614, T304-40, GHB119, MON88701 , 81910 in WO02 / 034946, W002 / 100163, W002 / 100163, W003 / 013224, WO04 / 072235, WO04 / 039986, WO05 / 103266, WO05 / 103266, WO06 / 128573, W007 / 017186, WO08 / 122406, W008 / 151780, WO12 / 134808, WO13 / 112527; for corn events GA21, MON810, DLL25, TC1507, MON863, MIR604, LY038, MON88017, 3272, 59122, NK603, MIR162, MON89034, 98140, 32138, MON87460, 5307, 4114, MON87427, DAS40278, MON87411 , 33121 , MON87403, MON87419 in W098 / 044140, US02 / 102582, US03 / 126634, WO04 / 099447, W004 / 011601, WO05 / 103301, W005 / 061720, W005 / 059103, WO06 / 098952, WO06 / 039376, US2007 / 292854, W007 / 142840, W007 / 140256, WO08 / 112019, W009 / 103049, WO09 / 111263, W010 / 077816, W011 / 084621 , W011 / 062904, WO11 / 022469, WO13 / 169923, WO14 / 116854, WO15 / 053998, WO15 / 142571 ; for potato events E12, F10, J3, J55, V11, X17, Y9 in WO14 / 178910, WO14 / 178913, WO14 / 178941, WO14 / 179276, WO16 / 183445,

[0981] W017 / 062831, W017 / 062825; for rice events LLRICE06, LLRICE601, LLRICE62 in WO00 / 026345, WO00 / 026356, WO00 / 026345; and for soybean events H7-1, MON89788, A2704-12, A5547-127, DP305423, DP356043, MON87701, MON87769, CV127, MON87705, DAS68416-4, MON87708, MON87712, SYHT0H2, DAS81419, DAS81419 x DAS44406-6, MON87751 in WO04 / 074492, WO06 / 130436, WO06 / 108674, WO06 / 108675, WO08 / 054747,250444W001

[0982] 89

[0983] W008 / 002872, WO09 / 064652, W009 / 102873, W010 / 080829, W010 / 037016, WO11 / 066384, W011 / 034704, W012 / 051199, W012 / 082548, W013 / 016527, W013 / 016516, W014 / 201235. The use of compounds I and compositions thereof, respectively, on cultivated plants may result in effects which are specific to a cultivated plant comprising a certain transgene or event. These effects might involve changes in growth behavior or changed resistance to biotic or abiotic stress factors (e.g. enhanced yield, early vigour, early or delayed ripening, changed amino acid or fatty acid spectrum or content; enhanced resistance or tolerance to insects, nematodes, fungal, bacterial, mycoplasma, viral orviroid pathogens; or cold or heat tolerance).

[0984] The compounds I and compositions thereof, respectively, are particularly suitable for controlling the following causal agents of plant diseases: Albugo spp. (white rust) on ornamentals, vegetables (e.g. A. Candida) and sunflowers (e.g. A. tragopogonis); Alternaria spp. (Alternaria leaf spot) on vegetables (e.g. A. dauci or A. porri), oilseed rape (A. brassicicola or brassicae), sugar beets (A. tenuis), fruits (A. grandis), rice, soybeans, potatoes and tomatoes (A. solani, A. grandis or A. alternata), tomatoes (A. solani or alternata) and wheat (A. triticina); Aphanomyces spp. on sugar beets and vegetables; Ascochyta spp. on vegetables and cereals (A. tritici on wheat; A. hordei on barley); Aureobasidium zeae (syn. Kapatiella zeae) on corn; Bipolaris and Drechslera spp. (teleomorph: Cochliobolus spp.), e.g. Southern leaf blight (D. maydis) or Northern leaf blight (B. zeicola) on corn; spot blotch (B. sorokiniana) on cereals and B. oryzae on rice and turfs; Blumeria (formerly Erysiphe) graminis (powdery mildew) on cereals (e.g. wheat or barley); Botrytis spp. e.g. B. cinerea (teleomorph: Botryotinia fuckeliana'. grey mold) on fruits and berries (e.g. strawberries), vegetables (e.g. lettuce, carrots, celery and cabbages); B. squamosa or B. allii on onions, oilseed rape, ornamentals (B eliptica), vines, forestry plants and wheat; Bremia lactucae (downy mildew) on lettuce; Ceratocystis (syn. Ophiostoma) spp. (rot or wilt) on broad-leaved trees and evergreens (C. ulmi on elm); Cercospora spp. (Cercospora leaf spots) on corn (C. zeae-maydis), rice, sugar beets (C. beticola), sugar cane, vegetables, coffee, soybeans (C. sojina or kikuchii) and rice; Cladobotryum (syn. Dactylium) spp. (C. mycophilum (teleomorph: Nectria albertinii, Nectria rosella syn. Hypomyces rosellus) on mushrooms; Clado-sporium spp. on tomatoes (C. fulvunr. leaf mold) and cereals (C. herbarum (black ear) on wheat); Claviceps purpurea (ergot) on cereals; Cochliobolus (anamorph: Helminthosporium or Bipolaris) spp. (leaf spots) on corn (C. carbonum), cereals (C. sativus, anamorph: B. sorokiniana) and rice (C. miyabeanus, anamorph: H. oryzae); Colletotrichum (teleomorph: Glomerella) spp. (anthracnose) on cotton (C. gossypii), corn (C. graminicola: stalk rot), soft fruits, potatoes (C. coccodes’. black dot), beans (C. lindemuthianum), soybeans (C. truncatum or gloeospori-oides), vegetables (C. lagenarium or capsici), fruits (e.g. C. acutatum), coffee (C. kahawae or coffeanum) and C. gloeosporioides on various crops; Corticium spp., e.g. C. sasakii (sheath blight) on rice; Corynespora cassiicola (leaf spots) on soybeans, cotton and ornamentals;

[0985] Cycloconium spp., e.g. C. oleaginum on olive trees; Cylindrocarpon spp. (fruit tree canker or young vine decline, teleomorph: Nectria or Neonectria spp.) on fruit trees, vines (C. liriodendri, teleomorph: Neonectria liriodendrr'. 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 (D. teres net blotch on barley; D. tritici-repentis tan spot on wheat), rice and turf; Esca (dieback, apoplexy) on vines, caused by Formitiporia (syn. Phellinus) punctata, F. mediterranea, Phaeomoniella chlamydospora, Phaeoacremonium aleophilum250444W001

[0986] 90

[0987] and / or Botryosphaeria obtusa’, Elsinoe spp. (anthracnose) on pome fruits (E. pyri), soft fruits (E. veneta) and vines (E ampelina)’ Entyloma oryzae (leaf smut) on rice; Epicoccum spp. (black mold) on wheat; Erysiphe spp. (powdery mildew) on sugar beets (E. betae), vegetables (e.g. E. p / s / ), such as cucurbits (E. cichoracearum), cabbages, oilseed 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. turcicum) Fusarium (teleomorph: Gibberella) spp. (wilt, root or stem rot) e.g. on cereals (F. graminearum or culmorurr. root rot, scab or head blight), tomatoes (F oxysporum), soybeans (E virguliforme, cuneirostruum, tucumaniae and brasiliense’. sudden death syndrome), and corn (E verticillioides) Gaeumannomyces graminis (take-all) on cereals (wheat, barley corn);

[0988] Gibberella spp. on cereals (G. zeae) and rice (G. fujikuror'. Bakanae disease); Glomerella cingulata on vines, pome fruits and cotton (G. gossypii)’ Grainstaining complex on rice;

[0989] Guignardia bidwellii (black rot) on vines; Gymnosporangium spp. on rosaceous plants (pears rust: G. sabinae) and junipers; Helminthosporium spp. (syn. Drechslera, teleomorph:

[0990] Cochliobolus) on corn, cereals, potatoes and rice; Hemileia spp., e.g. on coffee (H. vastatrix'. leaf rust); Isariopsis clavispora (syn. Pseudocercospora vitis) on vines; Macrophomina phaseolina (root and stem rot) on soybeans and cotton; Microdochium (syn. Fusarium) nivale (pink snow mold) on cereals (wheat or barley); Microsphaera diffusa (powdery mildew) on soybeans; Monilinia spp., e.g. M. laxa, fructicola and fructigena (bloom and twig blight, brown rot) on rosaceous plants (stone fruits); Mycosphaerella spp. on cereals ( / W. graminicola [anamorph: Zymoseptoria tritici formerly Septoria tritici. Septoria blotch on wheat), bananas (M. fijiensis [syn. Pseudocercospora fijiensis] : black Sigatoka disease; M. musicola), soft fruits, ground nuts ( / W. arachidis [anamorph: Cercospora arachidicola] or M. berkeleyi on peanuts), peas (M pisi), and brassicas ( / W. brassiciola) Peronospora spp. (downy mildew) on cabbage (P. brassicae), oilseed rape (P. parasitica), onions (P. destructor), tobacco (P. tabacina) and soybeans (P. manshurica) Phakopsora pachyrhizi and meibomiae (soybean rust) on soybeans; Phialophora spp. e.g. on vines (P. tracheiphila and tetraspora) and soybeans (P. gregata’. stem rot); Phoma spp. on oilseed rape and cabbage (P. lingam syn. Leptosphaeria maculans and biglobosa’. Phoma stem canker), sugar beet (P. betae’. root rot, leaf spot and damping-off) and corn (P. zeae-maydis, syn. Phyllostica zeae)’ Phomopsis spp. on sunflowers, vines (P. viticola cane and leaf spot) and soybeans (stem rot: P. phaseoli, teleomorph: Diaporthe phaseolorum)’ Physoderma maydis (brown spots) on corn; Phytophthora spp. (wilt, root, leaf, fruit and stem root) e.g. on paprika and cucurbits (P. capsici), soybeans (P. megasperma, syn. P. sojae), potatoes and tomatoes (P. infestans’. late blight), and broad-leaved trees (P. ramorunr. sudden oak death); Plasmodiophora brassicae (club root) e.g. on cabbage, oilseed rape, radish; Plas-mopara spp., on vines (P. viticola downy mildew) and sunflowers (P. halstedii)’ Podosphaera spp. (powdery mildew) on rosaceous plants, hop, pomes (P. leucotricha on apples), soft fruits and curcurbits (P. xanthii)’ Polymyxa spp. on cereals (P. graminis on wheat and barley) and sugar beets (P. betae) including thereby transmitted viral diseases; Pseudocercosporella herpotrichoides (syn. Oculimacula yallundae, O. acu for mis’. eyespot, teleomorph: Tapesia yallundae) on cereals, e.g. wheat or barley; Pseudoperonospora (downy mildew) e.g. on cucurbits (P. cubensis) and hop (P. humili)’ Pseudopezicula tracheiphila (red fire disease or ,rotbrenner’, anamorph: Phialophora) on vines; Puccinia spp. (rusts) e.g. on cereals (wheat, barley or rye: P. triticina’. brown or leaf rust, P. striiformis'. stripe or yellow rust, P. horder'. dwarf rust, P. graminis’. stem or black rust, P. recondita’. brown or leaf rust), sugar cane (P. kuehnir'.250444W001

[0991] 91

[0992] orange rust) and aspargus (P. asparagi) Pyrenopeziza spp. e.g. on oilseed rape (P. brassicae) Pyrenophora (anamorph: Drechslera) tritici-repentis (tan spot) on wheat or P teres (net blotch) on barley; Pyricularia spp., e.g. P. oryzae (teleomorph: Magnaporthe grisea rice blast) on rice and P. grisea on turf and cereals; Pythium spp. (damping-off) e.g. on turf, rice, corn, wheat, cotton, oilseed rape, sunflower, soybeans, sugar beets, vegetables (e.g. P. ultimum or aphani-dermatum) and mushrums (P. oligandrum) Ramularia spp., e.g. R. collo-cygni (Ramularia leaf spots) on barley, R. areola (teleomorph: Mycosphaerella areola) on cotton and R. beticola on sugar beets; Rhizoctonia spp. e.g. on cotton, rice, potatoes, turf, corn, oilseed rape, potatoes, sugar beets, vegetables, soybeans (R. solanr'. root and stem rot), rice (R. solanr'. sheath blight) and wheat and barley (R. cerealis'. spring blight); Rhizopus stolonifer (black mold, soft rot) on strawberries, carrots, cabbage, vines and tomatoes; Rhynchosporium seca / is and commune (scald) on barley, rye and triticale; Sarocladium oryzae and attenuatum (sheath rot) on rice; Sclerotinia spp. (stem rot or white mold) on vegetables (S. minor and S. sclerotiorum) and field crops, such as oilseed rape, sunflowers (S. sclerotiorum) and soybeans (S. sclerotiorum and rolfsii), peanut, vegetables, corn, cereals and ornamentals; Septoria spp. on various plants, e.g. S. glycines (brown spot) on soybeans, S. tritici (syn. Zymoseptoria tritici, Septoria blotch) on wheat and S. (syn. Stagonospora) nodorum (Stagonospora blotch) on cereals; Uncinula (syn. Erysiphe) necator (powdery mildew, anamorph: Oidium tucker!) on vines; Setosphaeria spp. (leaf blight) on corn (S. turcicum, syn. Helminthosporium) and turf; Sphacelotheca spp. (smut) on corn, (S. reiliana, syn. Ustilago'. head smut), sorghum und sugarcane; Sphaerotheca fuliginea (syn. Podosphaera xanthir'. powdery mildew) on cucurbits; Spongospora subterranea (powdery scab) on potatoes and thereby transmitted viral diseases; Stagonospora spp. on cereals (wheat: S. nodorum’. Stagonospora blotch, teleomorph: Leptosphaeria): 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 (wheat: T. triticr'. wheat bunt, T. contro-versa dwarf bunt); Trichoderma harzianum on mushrooms; Typhula incarnata (grey snow mold) on barley or wheat; Urocystis spp., e.g. U. occulta (stem smut) on rye; Uromyces spp. (rust) on vegetables (beans: U. appendiculatus, syn. phaseoli), sugar beets (U. betae or beticola) and on pulses (U. vignae, pisi, viciae-fabae and fabae): Ustilago spp. (loose smut) on cereals (U. nuda and avaenae), corn (U. maydis'. corn smut) and sugar cane; Venturia spp. (scab) on apples (V. inaequalis) and pears; and Verticillium spp. (wilt) e.g. on fruits (strawberry: V. dahliae), ornamentals, vines, soft fruits, vegetables and field crops (oilseed rape: V. longisporum), and mushrooms (V. fungicola): Zymoseptoria tritici on cereals.

[0993] The compounds I and compositions thereof, respectively, are particularly suitable for controlling the following causal agents of plant diseases: rusts on soybean and cereals (e.g. Phakopsora pachyrhizi and P. meibomiae on soy; Puccinia tritici and P. striiformis on wheat); molds on specialty crops, soybean, oil seed rape and sunflowers (e.g. Botrytis cinerea on strawberries and vines, Sclerotinia sclerotiorum, S. minor and S. rolfsii on oil seed rape, sunflowers and soybean); Fusarium diseases on cereals (e.g. Fusarium culmorum and P. graminearum on wheat); downy mildews on specialty crops (e.g. Plasmopara viticola on vines, Phytophthora infestans on potatoes); powdery mildews on specialty crops and cereals (e.g. Uncinula necator on vines, Erysiphe spp. on various specialty crops, Blumeria graminis on cereals); and leaf250444W001

[0994] 92

[0995] spots on cereals, soybean and corn (e.g. Septoria tritici and S. nodorum on cereals, S. glycines on soybean, Cercospora spp. on corn and soybean).

[0996] It has been observed that populations of phytopathogenic fungi apparently consisting of non-resistant strains can readily develop resistance. The compounds can be applied under such conditions, too, to prevent the formation of resistance and the spread of resistant strains altogether. In this regard it is useful that they have strong activity also against non-resistant phytopathogenic fungi.

[0997] Fungicide-resistant strains of various phytopathogenic fungi have been reported, with strains resistant to one or more fungicides from various mode of action classes being observed by target-site mutations in the genes of the respective proteins (e.g. Qol (C3, according to FRAC convention, for details www.frac.info), quinone outside stigmatellin binding subsite inhibitors (QoSI; C8), and quinone inside inhibitors (Qil; C4): CytB target protein; sterol demethylation (DMI, G1): Cyp51 [Erg11]; carboxylic acid amides (CAA, H5): CesA3; SDHI (C2): SdhB, SdhC and SdhD; dicarboximides (E3): Os-1 (including Bos1, Daf1 etc.); keto reductase inhibitors (KRI; Class III SBIs; G3): Erg27; and oxysterol binding protein inhibitors (OSBPI; F9): ORP1. Examples of mutation sites of genes encoding such target proteins resulting in the listed single amino acid exchanges, deletions or insertions in the respective target protein sequences conferring resistance against certain fungicides in phytopathogenic fungi are indicated in Table M (see also Pest Manag Sci 72(8) 2016: 1449-1459).

[0998] Table M:

[0999] Fungus Target proteins of fungicides: amino acid changes, de- letions, or insertions (separated by commas)

[1000] CytB: G143A; SdhB: H277R / Y; SdhC: H134R; SdhD: Alternaria alternata

[1001] H133R

[1002] A. arborescens CytB: G143A

[1003] A. brassicicola Os-1: E753K

[1004] A. longipes Os-1: G420D

[1005] CytB: F129L; Cyp51: L143F, G446S, G462S; SdhB:

[1006] A. solan!

[1007] H278R / Y; SdhC: N75S, H134R; SdhD: H133R

[1008] A. tomatophila CytB: G143A

[1009] Cyp51: Y132N, K197N, D282E, M288L, H399P, T469S, Aspergillus flavus

[1010] D411N, T454P

[1011] Cyp51: N22D, S52T, G54E / K / R / V / W**, Q88H, L98H, V101F, Y121F, N125I, G138C / R / S, Q141H, H147Y, F219S, A. fumigatus

[1012] M220K / I / T / V, T289A, S297T, P394L, Y431C, G432S, G434C, T440A, G448S, Y491H, F495I

[1013] A. parasiticus Cyp51: G54W

[1014]

[1015] 250444W001

[1016] 93

[1017] Fungus Target proteins of fungicides: amino acid changes, de- letions, or insertions (separated by commas) Blumeria graminis f. sp. horCytB: G143A; Cyp51: S97T, Y136F, K147Q, S509T de!

[1018] CytB: G143A; Cyp51: S79T, Y136F, K175N, V349A, B. g. f. sp. tritici

[1019] S509T

[1020] CytB: G143A; SdhB: P225H / F / L / T, N230I, H272L / R / V / Y:

[1021] SdhC: P80H / L, A85V; SdhD: H132R; Os-1: I365N / R / S. V368F, Q369H / P, N373S, T447S; Erq27: S9G, F26S, P57A, Botryotinia fuckeliana T63I, G170R, V192I, L195F, N196T, A210G, I232M,

[1022] P238S / A, P250S, P269L, AP298, V309M, A314V, S336C, V365A, E368D, N369D, E375K, A378T, L400F / S, Y408S, F412I / S / V / C, A461S, R496T

[1023] Cyp51: A61V, Y132F / H, K143E, S405F, F449S, G464S, Candida albicans

[1024] R467K, 1471 T

[1025] CytB: G143A; Cyp51: L144F, M145W, E297K, I309T, Cercospora beticola

[1026] I330T, P384S, I387M, E460Q, Y464S

[1027] C. sojina CytB: G143A

[1028] Cladosporium carpophilum CytB: G143A

[1029] Colletotrichum graminicola CytB: G143A

[1030] CytB: G143A; SdhB: H278R, H278Y, I280V; SdhC: S73P, Corynespora cassiicola

[1031] N75S; SdhD: S89P, G109V

[1032] Didymella rabiei CytB: G143A

[1033] CytB: G143A; Cyp51: Y136F; SdhB: H242R; I244V; SdhC: Erysiphe necator

[1034] A83V, G169D / S

[1035] Eurotium oryzae SdhB: H249L / N / Y; SdhC: T90I; SdhD: D124E Glomerella cingulata CytB: G143A

[1036] G. graminicola CytB: G143A

[1037] Magnaporthe oryzae CytB: F129L, G143A

[1038] Microdochium majus; nivale CytB: G143A

[1039] Monilinia fructicola Cyp51: Y136F, A381G

[1040] CytB: G143A; Cyp51: S97T, Y136F, A313G, A381G, Mycosphaerella fijiensis

[1041] Y461D, G462A, Y463D / H / N

[1042] Parastagonospora nodorum CytB: G143A; Cyp51: Y134F

[1043] CytB: F129L; Cyp51: F120L, V130A, Y131F / H, K142R, Phakopsora pachyrhizi

[1044] I145F / V, F154Y, I475T; SdhC: I86F, N88S / D, G92R, H154R,

[1045]

[1046] 250444W001

[1047] 94

[1048] Fungus Target proteins of fungicides: amino acid changes, de- letions, or insertions (separated by commas) CesA3: Q1077K, V1109L / M; ORP1*: L733W, N767I, Phytophthora capsici S768F / Y, G770V, AG818+AF819, N835S / A, N837F,

[1049] N837T+S910C, G839W, P861H, L863W, I877F / Y

[1050] P. drechsleri CesA3: V1109L

[1051] CesA3: G1105S / A / V, V1109L; ORP1*: G770V, N837I / F / L, P. infestans

[1052] I877F

[1053] ORP1*: L733W, S768F, S768Y, N837F, N837Y, P861H, P. sojae

[1054] L863W, I877Y

[1055] CytB: S34L, F129L, G143A, L201S, E203-DE-V204#, Plasmopara viticola E203-VE-V204#; E203-E-V204#; CesA3: G1105S / V; ORP1:

[1056] N837I, I877F

[1057] Plenodomus biglobosus SdhB: H274Y, I276V; SdhC: S132R

[1058] CytB: G143A; SdhB: P225L, H272R / Y; Os-1: F267L, Pleospora aim

[1059] L290S, T765R, Q777R

[1060] Podosphaera fusca CytB: G143A

[1061] P. leucotricha SdhC: G149R

[1062] CytB: G143A; SdhB: K39E, N201I, I245V; SdhC: A86V, P. xanthii

[1063] G151R, G172D, S176D; SdhD: S121P, H137R / Q Pseudoperonospora cuben- CytB: G143A; CesA3: G1105V / W; ORP1*: G705V, L798W, sis I812F

[1064] Puccinia triticina Cyp51: Y134F; SdhC: I87F, N89S / K

[1065] Pyrenopeziza brassicae Cyp51: S508T

[1066] CytB. F129L; G143A; SdhB: H277Y; SdhC: K49E, R64K, Pyrenophora teres S73P, N75S, G79R, H134R, S135R; SdhD: D124E / N,

[1067] H134R / Y, G138V, D145G, E178K

[1068] P. tritici-repentis CytB: F129L, G137R, G143A

[1069] Pythium aphanidermatum CytB: F129L

[1070] CytB: G143A; Cyp51: A311S, I325T, I328L, I381T, I384L, Y405H, D458G, Y459C / N, G460D / V, Y461H, Y461N; SdhB: Ramularia collo-cygni

[1071] N224T, R264P, H266L / R / Y, T267I, I268V, R364P; SdhC: N87S / Y, G91R, H146R / L, R152M, H153R, G171D Rhynchosporium secalis CytB: G143A; SdhC: N85S

[1072] Saccharomyces cerevisiae Cyp51: Y140F / H

[1073]

[1074] 250444W001

[1075] 95

[1076] Fungus Target proteins of fungicides: amino acid changes, de- letions, or insertions (separated by commas)

[1077] SdhB: H273R, H273Y; SdhC: G91R, H146R, G150R;

[1078] Sclerotinia sclerotiorum

[1079] SdhD: T108K, H132R

[1080] Stagonosporopsis cucurSdhB: H277R, H277Y

[1081] bitacearum

[1082] Thanatephorus cucumeris CytB: F129L

[1083] Ustilago maydis SdhB: H257L

[1084] CytB: G143A: Cyp51: V132A, Y133F, L140F, M141V, Venturia inaequalis M141T, M190L, E441K / G, D442H / Y, Y443C / D, G444D / S, Y445H / S; SdhB: T253I; SdhC: N85S, H151R

[1085] CytB: G37V, F129L, Y132C, G137R, G143A; Cyp51: L50S, D107V, D134G, V136A / C / G, Y137F, M145L, N178S, S188N, S208T, N284H, H303Y, A311G, G312A, A379G, I381V / P / A, A410T, G412A, Y459C / D / N / S / P / A, G460D, AG460, Zymoseptoria tritici Y461D / H / S, V490L, G510C, N513K, S524T; SdhB: N225I / T,

[1086] T268I / A, I269V, H273Y; SdhC: I29V, N33T, N34T, T79I / N, W80L / S, A84I / V, L85P, N86K / S / A / G, G90R, H145R, R151M / G / T / S, H152R / Y, 1161 S, V166M, G170D; SdhD: R47W, I50F, M114V, D129E / G / S / T, R135S, G179D, K186R

[1087]

[1088] * based on alignment to reference sequence from Phytophthora infestans ** G54E / K / R / V / W indicates the possibility of five different amino acid changes at position 54; A indicates a deletion of an amino acid; # refers to an amino acid insertion.

[1089] Thus, compounds I are particularly useful to control such fungicide-resistant strains of phytopathogenic fungi described in Table M. Such strains may have one or more resistances derived from one or more mutations of one or more genes encoding target proteins of various kinds of the fungicides including, but not limited to, the mutations listed in Table M and / or a resistance derived from an overexpression of the respective target protein.

[1090] In addition, certain strains of fungi may have developed so-called multidrug resistance eventually leading to a broad cross resistance to many structurally and functionally unrelated compounds. "Multidrug resistance” (MDR) also called “pleiotropic drug resistance” (PDR) describes a resistance phenomenon usually caused by overexpression of certain membrane transporters, leading to an increased activity of efflux pump which export certain substrates, e.g., fungal toxins but also fungicidal compounds. Examples of such membrane transporters include ATP-binding cassette (ABC) transporters and Major Facilitator Superfamily (MFS) transporters. Overexpression of membrane transporters can be confirmed, e.g., by measuring an amount of the transporter protein or of the corresponding mRNA. The measured amount of mRNA may be, e.g., 2-fold, 5-fold, 20-fold, up to 100-fold or more, relative to the mRNA amount of the corresponding fungicide-sensitive wild-type fungus.

[1091] The compounds I of the present invention can be applied to control a plant disease that is caused by a multidrug-resistant (MDR) fungus. The multidrug-resistant fungus may have in250444W001

[1092] 96

[1093] addition one or more resistances derived from one or more mutations of one or more genes encoding target proteins of various kinds of the fungicides including but not limited to the mutations listed in Table M and / or a resistance derived from an overexpression of the target protein. Thus, compounds I are also particularly useful to control such multidrug-resistant fungi.

[1094] The compounds I and compositions thereof, respectively, are also suitable for controlling harmful microorganisms in the protection of stored products or harvest, and in the protection of materials.

[1095] The term "stored products or harvest" is understood to denote natural substances of plant or animal origin and their processed forms for which long-term protection is desired. Stored products of plant origin, for example stalks, leaves, tubers, seeds, fruits or grains, can be protected in the freshly harvested state or in processed form, such as pre-dried, moistened, comminuted, ground, pressed or roasted, which process is also known as post-harvest treatment. Also falling under the definition of stored products is timber, whether in the form of crude timber, such as construction timber, electricity pylons and barriers, or in the form of finished articles, such as furniture or objects made from wood. Stored products of animal origin are hides, leather, furs, hairs and alike. Preferably, "stored products" is understood to denote natural substances of plant origin and their processed forms, more preferably fruits and their processed forms, such as pomes, stone fruits, soft fruits and citrus fruits and their processed forms, where application of compounds I and compositions thereof can also prevent disadvantageous effects such as decay, discoloration or mold.

[1096] 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, paperboard, textiles, leather, paint dispersions, plastics, cooling lubricants, fiber, or fabrics against the infestation and destruction by harmful microorganisms, such as fungi and bacteria.

[1097] 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.

[1098] The compounds I and compositions thereof, respectively, 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.

[1099] 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.

[1100] The compounds I are employed as such or in form of compositions by treating the fungi, the plants, plant propagation materials, such as seeds; soil, surfaces, materials, or rooms to be250444W001

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[1102] 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.

[1103] An agrochemical composition comprises a fungicidally effective amount of a compound I. The term "fungicidally 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 stored products or harvest or of materials and which does not result in a substantial damage to the treated plants, the treated stored products or harvest, or to the treated materials. 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, stored product, harvest or material, the climatic conditions, and the specific compound I used.

[1104] 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. 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.

[1105] In treatment of plant propagation materials such as seeds, e.g. by dusting, coating, or drenching, amounts of active substance of generally 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 kg of plant propagation material (preferably seeds) are required.

[1106] The user applies the agrochemical composition 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.

[1107] The compounds I and the compositions containing them may be applied in combination with, or by utilizing smart agricultural technologies, such as precision agriculture, remote and proximate imaging and image recognition, or smart agricultural site management programs. Such technologies typically include models, e.g. computer programs, that support the user by considering information from a variety of sources to increase quality and yield of harvested material, reduce damage by pests including the prediction of pest pressure and smart application of crop protection products, secure environmental protection, support quick and reliable agronomic decision making, reduce usage of fertilizers and crop protection products, reduce product residues in consumables, increase spatial and temporal precision of agronomical measures, automate processes, and enable traceability of measures. Commercially available systems which include agronomic models are e.g. FieldScripts™ (The Climate Corporation), Xarvio™ (BASF) and AGLogic™ (John Deere).

[1108] Information input for these models includes, but is not limited to, soil data, information on: the plants that are currently growing or that may grow at the area of interest including crops and / or unwanted vegetation, weather, the location of the area and directly derivable information thereof, pest pressure, beneficial organisms; comprising forecast, present and / or historic250444W001

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[1110] information of any of the aforementioned.

[1111] The information usable for precision agriculture may be based on input by at least one user, be accessible from external data sources and databases, or be based on sensor data. Data sources typically include proximate-detection systems like soil-borne sensors and remote sensing as may be achieved by imaging with unmanned airborne vehicles like drones, or satellites. Sensors may be included in an Internet-of-Things system and may be directly or indirectly connected to the processing unit, e.g. via a wireless network and / or cloud applications. The information is typically taken into account by at least one processing unit and used to provide recommendations, and to generate control signals.

[1112] Typical technologies that are used in smart agricultural technologies include self-steering robots (such as tractors, harvesters, drones), artificial intelligence (e.g. machine learning), imaging technologies (e.g. image segmentation technologies), big data analysis, model generation, cloud computing, and machine-to-machine communication.

[1113] Precision agriculture or farming is characterized by spatially and / or temporally resolved, targeted application of active ingredients like pesticides, plant-growth-regulators, fertilizers, and / or water including the variation of application rates over the agronomic site, zone or spot application, and of the spatially and / or temporally resolved, targeted planting or seeding of desired plant propagation material to an agronomic site. Precision farming typically includes the use of geo-positioning technologies like GPS for gaining information on the location and boundaries of the area of interest, the utilized application equipment, sensing equipment and recorded data, and to control the actions of farm vehicles such as spraying. By combining geopositioning data with (digital) maps, it is possible to (semi)-automate agricultural measures at the site of interest, e.g. by using (semi)-autonomous spraying or seeding equipment. Precision farming typically includes the application of smart spraying equipment, e.g. spot spraying, and precision spraying, e.g. by irrigation systems, tractors, robots, helicopters, airplanes, unmanned aerial vehicles, such as drones. Such equipment usually includes input sensors (e.g. camera) and a processing unit configured to analyze the input data and configured to provide a recommendation or decision based on the analysis of input data to apply the compounds I or compositions comprising them to the agronomic site, e.g. the soil, the crop plants, or to control pests in a specific and precise manner. Pests may be detected, identified, and / or classified from imagery acquired by a camera. Such identification and classification can make use of image processing algorithms, which may utilize artificial intelligence (e.g. machine learning algorithms), or decision trees. In this manner, the compounds I or compositions described herein can be applied only at the required location, point in time and dose rate.

[1114] The compounds I can be converted into customary types of agrochemical compositions, such as solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof. Examples for composition types (see also “Catalogue of pesticide formulation types and international coding system”, Technical Monograph No. 2, 8thEd. May 2022, CropLife International) 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). The compositions are250444W001

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[1116] prepared in a known manner (e.g. Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2000; Agrow Reports DS243, T&F Informa, London, 2005). The invention also relates to agrochemical compositions comprising an auxiliary and at least one compound I. 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.

[1117] 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, and alkylated naphthalenes; alcohols, e.g. ethanol, propanol, butanol, benzyl alcohol, cyclohexanol, glycols; DMSO; ketones, e.g. cyclohexanone; esters, e.g. lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e.g.

[1118] / V-methyl pyrrolidone, fatty acid dimethyl amides; and mixtures thereof.

[1119] 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.

[1120] 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 emulsifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid, or adjuvant. Examples of surfactants are listed in McCutcheon’s, Vol.1: Emulsifiers & Detergents, MC Publishing, USA, 2020 (Int. Ed.; 978-0944254806).

[1121] Suitable anionic surfactants are alkali, alkaline earth metal or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof. Examples of sulfonates are alkylaryl sulfonates, diphenyl sulfonates, alpha-olefin sulfonates, lignin 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 of alkyl naphthalenes, sulfosuccinates, or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids, of 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, / V-substituted 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.

[1122] Examples of / V-substituted 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 glucose250444W001

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[1124] esters, or alkylpolyglucosides. Examples of polymeric surfactants are home- or copolymers of vinyl pyrrolidone, vinyl alcohols, or vinyl acetate.

[1125] 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-Atype 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 polyvinyl amines or polyethylene amines.

[1126] Suitable adjuvants are compounds, which have a negligible 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 auxiliaries, e.g. as listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5. Suitable thickeners are polysaccharides (e.g. xanthan gum, carboxymethyl cellulose), inorganic clays (organically modified or unmodified), polycarboxylates, and silicates. Suitable bactericides are bronopol and isothiazolinone derivatives, such as alkylisothiazolinones and benzisothiazo-linones. 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 polyvinyl pyrrolidones, polyvinyl acetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.

[1127] The agrochemical compositions generally comprise between 0.01 and 95 %, preferably between 0.1 and 90 %, more preferably between 1 and 70 %, and in particular between 10 and 60 %, by weight of active substances (e.g. at least one compound I). The agrochemical compositions generally comprise between 5 and 99.9 %, preferably between 10 and 99.9 %, more preferably between 30 and 99 %, and in particular between 40 and 90 %, by weight of at least one auxiliary. The active substances (e.g. compounds I) are employed in a purity of 90 % to 100 %, preferably 95 % to 100 % (according to NMR spectrum).

[1128] For the purposes of treatment of plant propagation materials, particularly seeds, solutions for seed treatment (LS), suspo-emulsions (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. The compositions in question give, after two-to-tenfold dilution, active substance concentrations of 0.01 to 60 % by weight, preferably 0.1 to 40 %, in the ready-to-use preparations. Application can be carried out before or during sowing. Methods for applying compounds I and compositions thereof, respectively, onto plant propagation material, especially seeds, include dressing, coating, pelleting, dusting, soaking, as well as in-furrow application. Preferably, compounds I or the compositions thereof, respectively, are applied onto plant propagation material by a method such that germination is not induced, e.g. by seed dressing, pelleting, coating, and dusting. Various types of oils, wetters, adjuvants, fertilizers, or micronutrients, and further pesticides (e.g.250444W001

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[1130] fungicides, growth regulators, herbicides, insecticides, safeners) may be added to the compounds I or the compositions thereof as premix, or, 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.

[1131] A pesticide is generally a chemical or biological agent (such as pesticidal active ingredient, compound, composition, virus, bacterium, antimicrobial, or disinfectant) that through its effect deters, incapacitates, kills, or otherwise discourages pests. Target pests can include insects, plant pathogens, weeds, mollusks, birds, mammals, fish, nematodes (roundworms), and microbes that destroy property, cause nuisance, spread disease or are vectors for disease. The term “pesticide” includes also plant growth regulators that alter the expected growth, flowering, or reproduction rate of plants; defoliants that cause leaves or other foliage to drop from a plant, usually to facilitate harvest; desiccants that promote drying of living tissues, such as unwanted plant tops; plant activators that activate plant physiology for defense of against certain pests; safeners that reduce unwanted herbicidal action of pesticides on crop plants; and plant growth promoters that affect plant physiology e.g. to increase plant growth, biomass, yield or any other quality parameter of the harvestable goods of a crop plant.

[1132] Biopesticides have been defined (http: / / www.epa.gov / pesticides / biopesticides / ) as a form of pesticides based on microorganisms (bacteria, fungi, viruses, nematodes, etc.) or natural products (compounds, such as metabolites, proteins, or extracts from biological or other natural sources). Biopesticides fall into two major classes, microbial and biochemical pesticides:

[1133] (1) Microbial pesticides consist of bacteria, fungi or viruses (and often include the metabolites that bacteria and fungi produce). Entomopathogenic nematodes are also classified as microbial pesticides, even though they are multi-cellular.

[1134] (2) Biochemical pesticides are naturally occurring substances that control pests or provide other agricultural uses and are relatively non-toxic to mammals.

[1135] Mixing compounds I or compositions comprising them with other fungicides results often in an expansion of the fungicidal spectrum or in prevention of fungicide resistance development. Furthermore, in many cases, synergistic effects are obtained (synergistic mixtures).

[1136] The following list of pesticides II, in conjunction with which compounds I can be used, is intended to illustrate the possible combinations but does not limit them (sorted by mode of action and target site, FRAC or IRAC code in brackets; www.frac.info; FRAC code list 2024; www.irac-online.org; IRAC MCA classification scheme 2024):

[1137] A) Respiration (C)

[1138] complex III at Qosite (Qol, C3): azoxystrobin (A.1.1), bifemetstrobin (A.1.24), bifujunzhi (A.1.37), coumethoxystrobin (A.1.2), coumoxystrobin (A.1.3), dimoxystrobin (A.1.4), ene- stroburin (A.1.5), famoxadone (A.1.21), fenamidone (A.1.23), fenaminstrobin (A.1.6), flufen- oxystrobin (A.1.7), fluoxastrobin (A.1.8), kresoxim-methyl (A.1.9), mandestrobin (A.1.10), metominostrobin (A.1.11), metyltetraprole (A.1.25; member of MoA subgroup A), orysa- strobin (A.1.12), picoxystrobin (A.1.13), pyraclostrobin (A.1.14), pyrametostrobin (A.1.15), pyraoxystrobin (A.1.16), pyribencarb (A.1.19), pyriminostrobin (A.1.36), triclopyricarb250444W001

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[1140] (A.1.20), trifloxystrobin (A.1.17), 2-(2-(3-(2,6-dichlorophenyl)-1-methyl-allylideneaminooxy- methyl)-phenyl)-2-methoxyimino- / V-methyl-acetamide (A.1.18), methyl- / V-[2-[(1 ,4-dimethyl- 5-phenyl-pyrazol-3-yl)oxylmethyl]phenyl]- / V-methoxy-carbamate (A.1.22), (Z,2E)-5-[1-(2,4-di- chlorophenyl)pyrazol-3-yl]-oxy-2-methoxyimino-A / ,3-dimethyl-pent-3-enamide (A.1.34), (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino- / V,3-dimethyl-pent-3-enamide (A.1.35), 2-(ortho-((2,5-dimethylphenyl-oxymethylen)phenyl)-3-methoxy-acrylic acid methylester (A.1.38), methyl (Z)-3-methoxy-2-[2-methyl-5-(3-propylpyrazol-1-yl)phenoxy]- prop-2-enoate, methyl (Z)-2-[5-(3-isopropylpyrazol-1-yl)-2-methyl-phenoxy]-3-methoxy-prop- 2-enoate, methyl (Z)-3-methoxy-2-[2-methyl-5-[3-(trifluoromethyl)pyrazol-1-yl]phenoxy]prop- 2-enoate, methyl (Z)-3-methoxy-2-[2-methyl-5-(4-propyltriazol-2-yl)phenoxy]prop-2-enoate, methyl (Z)-3-methoxy-2-[2-methyl-5-[4-(trifluoromethyl)triazol-2-yl]phenoxy]prop-2-enoate, methyl (Z)-2-[5-(4-isopropyltriazol-2-yl)-2-methyl-phenoxy]-3-methoxy-prop-2-enoate, methyl (Z)-2-(5-cyclobutyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate, methyl (Z)-2-(5-cyclopent- yl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate, methyl (Z)-2-(5-cyclopropyl-2-methyl-phen- oxy)-3-methoxy-prop-2-enoate, methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy- prop-2-enoate, methyl (E)-3-methoxy-2-[(2-methyl-5-phenyl-phenyl)methyl]prop-2-enoate, methyl (E)-3-methoxy-2-[[5-[(E)- / V-methoxy-C-methyl-carbonimidoyl]-2,4-dimethyl-phenyl]- methyl]prop-2-enoate; methyl (E)-2-[[5-(2-cyclopropylethynyl)-2,4-dimethyl-phenyl]methyl]- 3-methoxy-prop-2-enoate; methyl (E)-3-methoxy-2-(2-phenyl-1 ,3-benzoxazol-4-yl)prop- 2-enoate; methyl (E)-3-methoxy-2-(2-phenyl-1,3-benzothiazol-4-yl)prop-2-enoate; methyl (E)-3-methoxy-2-(2-phenyl-1 ,3-benzoxazol-7-yl)prop-2-enoate; methyl (Z)-2-[6-(2-cycloprop- ylethynyl)benzimidazol-1-yl]-3-methoxy-prop-2-enoate; methyl (Z)-3-methoxy-2-(6-phenyl- benzimidazol-1-yl)prop-2-enoate; methyl (Z)-2-(3-chloro-6-phenyl-indol-1-yl)-3-methoxy- prop-2-enoate; methyl (Z)-2-(2,3-dichloro-6-phenyl-indol-1-yl)-3-methoxy-prop-2-enoate; methyl (Z)-3-methoxy-2-[6-[(E)-methoxyiminomethyl]indol-1-yl]prop-2-enoate; methyl (Z)-3-methoxy-2-[6-[(E)- / V-methoxy-C-methyl-carbonimidoyl]indol-1-yl]prop-2-enoate, methyl / V-[[5-[1-(2,6-difluoro-4-isopropyl-phenyl)pyrazol-3-yl]-2-methyl-phenyl]methyl]carbamate, methyl / V-[[5-[1-(4-cyclopropyl-2,6-difluoro-phenyl)pyrazol-3-yl]-2-methyl-phenyl]methyl]- carbamate, methyl / V-[[5-[1-(4-chloro-2,6-difluoro-phenyl)pyrazol-3-yl]-2-methyl-phenyl]- methyl]carbamate, methyl / V-[[5-[1-[2,6-difluoro-4-(trifluoromethyl)phenyl]pyrazol-3-yl]- 2-methyl-phenyl]methyl]carbamate;

[1141] - complex III at Qi site (Qil, C4): cyazofamid (A.2.1), amisulbrom (A.2.2),

[1142] [(6S,7R,8R)-8-benzyl-3-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]-6-methyl-4,9-di- oxo-1,5-dioxonan-7-yl]-2-methylpropanoate (A.2.3), fenpicoxamid (A.2.4), florylpicoxamid (A.2.5), metarylpicoxamid (A.2.6);

[1143] - complex II (SDHI, C2): benodanil (A.3.1), benzovindiflupyr (A.3.2), bixafen (A.3.3), boscalid (A.3.4), carboxin (A.3.5), cyclobutrifluram (A.3.24), fenfuram (A.3.6), fluopyram (A.3.7), flutolanil (A.3.8), fluxapyroxad (A.3.9), furametpyr (A.3.10), inpyrfluxam (A.3.22), isofetamid (A.3.11), isoflucypram (A.3.31), isopyrazam (A.3.12), mepronil (A.3.13), oxycarboxin (A.3.14), penflufen (A.3.15), penthiopyrad (A.3.16), pydiflumetofen (A.3.17), pyrapropoyne (A.3.23), pyraziflumid (A.3.18), sedaxane (A.3.19), tecloftalam (A.3.20), thifluzamide (A.3.21), fluindapyr (A.3.28), / V-[2-[2-chloro-4-(trifluoromethyl)phenoxy]phenyl]- 3-(difluoromethyl)-5-fluoro-1-methyl-pyrazole-4-carboxamide (A.3.29), methyl (E)-2-[2-[(5-cy- ano-2-methyl-phenoxy)methyl]phenyl]-3-methoxy-prop-2-enoate (A.3.30), 2-(difluoromethyl)-250444W001

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[1145] A / -(1 , 1 ,3-trimethyl-indan-4-yl)pyridine-3-carboxamide (A.3.32), 2-(difluoromethyl)- / V-[(3R)-1 ,1 ,3-trimethylindan-4-yl]pyridine-3-carboxamide (A.3.33), 2-(difluoromethyl)- A / -(3-ethyl- 1 ,1-dimethyl-indan-4-yl)pyridine-3-carboxamide (A.3.34), 2-(difluoromethyl)- / V-[(3R)-3-ethyl-1 ,1-dimethyl-indan-4-yl]pyridine-3-carboxamide (A.3.35), 2-(difluoromethyl)- / V-(1 ,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide (A.3.36), 2-(difluoromethyl)- / V-[(3R)-1 ,1-dimethyl-3-propyl-indan-4-yl]pyridine-3-carboxamide (A.3.37), 2-(difluoromethyl)- A / -(3-isobutyl- 1 ,1-dimethyl-indan-4-yl)pyridine-3-carboxamide (A.3.38), 2-(difluoromethyl)- / V-[(3R)-3-isobutyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide (A.3.39);

[1146] - complex I NADH oxido-reductase (C1): diflumetorim (A.4.1);

[1147] - uncouplers (C5): binapacryl (A.4.2), dinobuton (A.4.3), dinocap (AAA), fluazinam (AA.5), meptyldinocap (AA.6), ferimzone (AA.7);

[1148] - inhibitors of ox. phosphorylation (C6): fentin salts, e.g. fentin-acetate (A.4.8), fentin chloride (A.4.9) or fentin hydroxide (A.4.10);

[1149] - ATP transport: silthiofam (A.4.11);

[1150] - quinone inside and outside inhibitor stigmatellin binding type (QioSI; C8): ametoctradin (A.5.1);

[1151] B) Sterol biosynthesis (G)

[1152] - C14 demethylase (DMI, G1): triazoles: azaconazole (B.1.1), bitertanol (B.1.2), bromucon- azole (B.1.3), cyproconazole (B.1.4), difenoconazole (B.1.5), diniconazole (B.1.6), dinicon- azole-M (B.1.7), epoxiconazole (B.1.8), fenbuconazole (B.1.9), fluoxytioconazole (B.1.33), fluquinconazole (B.1.10), flusilazole (B.1.11), flutriafol (B.1.12), hexaconazole (B.1.13), imi- benconazole (B.1.14), ipconazole (B.1.15), ipfentrifluconazole (B.1.37), mefentrifluconazole (B.1.38), metconazole (B.1.17), myclobutanil (B.1.18), oxpoconazole (B.1.19), paclobutra- zole (B.1.20), penconazole (B.1.21), propiconazole (B.1.22), prothioconazole (B.1.23), simeconazole (B.1.24), tebuconazole (B.1.25), tetraconazole (B.1.26), triadimefon (B.1.27), triadimenol (B.1.28), triticonazole (B.1.29), uniconazole (B.1.30), 2-(2,4-difluorophenyl)- 1 , 1 -difluoro-3-(tetrazol-1 -yl)- 1 -[5-[4-(2,2,2-trifluoroethoxy)phenyl]-2-pyridyl]propan-2-ol (B.1.31), 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[4-(trifluoromethoxy)phenyl]- 2-pyridyl]propan-2-ol (B.1.32), 2-(chloromethyl)-2-methyl-5-(p-tolylmethyl)-1-(1 ,2,4-triazol- 1-ylmethyl)cyclopentanol (B.1.43), 4-[[6-[2-(2,4-difluorophenyl)-1 ,1-difluoro-2-hydroxy- 3-(1 ,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile (B.1.53), 2-[6-(4-bromophenoxy)- 2-(trifluoromethyl)-3-pyridyl]-1-(1 ,2,4-triazol-1-yl)propan-2-ol (B.1.54), 2-[6-(4-chlorophen- oxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1 ,2,4-triazol-1-yl)propan-2-ol (B.1.55), (2R)-2-[4-(4-chlo- rophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, (2S)-2-[4-(4-chlo- rophenoxy)-2-(trifluoromethyl)phenyl]-1-(1 ,2,4-triazol-1-yl)propan-2-ol, methyl 2-[2-chloro- 4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1 ,2,4-triazol-1-yl)propanoate (B.1.56), 2-[2-chloro- 4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoic acid (B.1.57); imidazoles: imazalil (B.1.44), pefurazoate (B.1.45), prochloraz (B.1.46), triflumizole (B.1.47); pyrimidines, pyridines, piperazines: fenarimol (B.1.49), pyrifenox (B.1.50), triforine (B.1.51), [3-(4-chloro-2-fluoro-phenyl)-5-(2,4-difluorophenyl)isoxazol-4-yl]-(3-pyridyl)methanol (B.1.52);

[1153] - delta14-reductase (G2): aldimorph (B.2.1), dodemorph (B.2.2), dodemorph-acetate (B.2.3),250444W001

[1154] 104

[1155] fenpropidin (B.2.6), fenpropimorph (B.2.4), piperalin (B.2.7), spiroxamine (B.2.8), tridemorph (B.2.5);

[1156] - 3-keto reductase (G3): fenhexamid (B.3.1), fenpyrazamine (B.3.2);

[1157] - other: chlorphenomizole (B.4.1);

[1158] C) Nucleic acids metabolism (A)

[1159] - RNA polymerase I (A1): benalaxyl (C.1.1), benalaxyl-M (C.1.2), kiralaxyl (C.1.3), metalaxyl (C.1.4), metalaxyl-M (C.1.5), ofurace (C.1.6), oxadixyl (C.1.7);

[1160] - adenosine deaminase (A2): bupirimate (C.2.4), 5-fluoro-2-(p-tolylmethoxy)pyrimidin-4-amine (C.2.6), 5-fluoro-2-(4-fluorophenylmethoxy)pyrimidin-4-amine (C.2.7), 5-fluoro-2-(4-chloro- phenylmethoxy)pyrimidin-4-amine (C.2.8);

[1161] - DNA / RNA synthesis (A3): 5-fluorocytosine (C.2.5), hymexazole (C.2.1), octhilinone (C.2.2), - gyrase (A4): oxolinic acid (C.2.3);

[1162] - dihydroorotate dehydrogenase (DHODH; A5): ipflufenoquin (C.5.1), quinofumelin (C.5.2), feneptamidoquin (C.5.3);

[1163] D) Cytoskeleton and motor protein (B)

[1164] - tubulin polymerization (MBC; B1): benomyl (D.1.1), carbendazim (D.1.2), fuberidazole (D.1.3), pyridachlometyl (D.1.6), thiabendazole (D.1.4), thiophanate-methyl (D.1.5), / V-ethyl- 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]butanamide (D.1.8), / V-ethyl-2-[(3-ethynyl-8-methyl- 6-quinolyl)oxy]-2-methylsulfanyl-acetamide (D.1.9), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]- / V-(2-fluoroethyl)butanamide (D.1.10), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]- / V-(2-fluoroeth- yl)-2-methoxy-acetamide (D.1.11), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]- / V-propyl- butanamide (D.1.12), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methoxy- / V-propyl-acetamide (D.1.13), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methylsulfanyl- / V-propyl-acetamide (D.1.14), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]- / V-(2-fluoroethyl)-2-methylsulfanyl-acetamide (D.1.15), 4-(2-bromo-4-fluoro-phenyl)- / V-(2-chloro-6-fluoro-phenyl)-2,5-dimethyl-pyrazol- 3-amine (D.1.16), 4-(2-bromo-4-fluorophenyl)- / V-(2-fluoro-6-nitrophenyl)-1,3-dimethyl- 1 H-pyrazol-5-amine, 4-(2-chloro-4,6-difluorophenyl)- / V-(2-fluoro-6-nitrophenyl)-1 ,3-dimethyl- 1H-pyrazol-5-amine, 4-(2-chloro-4-fluorophenyl)- / V-(2-fluoro-6-nitrophenyl)-3-ethyl-1-methyl- 1 H-pyrazol-5-amine, 4-(2-chloro-4-fluorophenyl)- / V-(2-fluoro-4-methyl-6-nitrophenyl)-1 ,3-di- methyl-1 H-pyrazol-5-amine, 4-(2-chloro-4-fluorophenyl)- / V-(2-fluoro-6-nitrophenyl)-1 ,3-di- methyl-1H-pyrazol-5-amine, 4-(2,4-difluorophenyl)- / V-(2-fluoro-6-nitrophenyl)-1,3-dimethyl- 1H-pyrazol-5-amine;

[1165] - tubulin polymerization (B2): diethofencarb (D.2.1),

[1166] - tubulin polymersation (B3): ethaboxam (D.2.2), zoxamide (D.2.5);

[1167] - cell division (B4): pencycuron (D.2.3);

[1168] - spectrin-like proteins (B5): fluopicolide (D.2.4), fluopimomide (D.2.9);

[1169] - actin / myosin / fimbrin function (B6): metrafenone (D.2.6), phenamacril (D.2.8), pyriofenone (D.2.7);

[1170] E) Amino acids and protein synthesis (D)250444W001

[1171] 105

[1172] - methionine synthesis (D1): cyprodinil (E.1.1), mepanipyrim (E.1.2), pyrimethanil (E.1.3); - ribosome, termination step (D2): blasticidin-S (E.2.1);

[1173] - ribosome initiation step (D3): kasugamycin (E.2.2), kasugamycin hydrochloride-hydrate (E.2.3);

[1174] - ribosome initiation step (D4): streptomycin (E.2.5);

[1175] - ribosome elongation step (D5): mildiomycin (E.2.4), oxytetracyclin (E.2.6);

[1176] F) Signal transduction

[1177] - mechanism unknown (E1): proquinazid (F.2.2), quinoxyfen (F.2.1);

[1178] - MAP / histidine kinase os-2 (E2): fludioxonil (F.1.5);

[1179] - MAP / histidine kinase os-1 (E3): iprodione (F.1.2), procymidone (F.1.3), vinclozolin (F.1.4); G) Lipid synthesis or transport / membrane (F)

[1180] - methyl transferase (F2): edifenphos (G.1.1), iprobenfos (G.1.2), isoprothiolane (G.1.4); pyrazophos (G.1.3);

[1181] - cell peroxidation (F3): biphenyl (G.2.5), chloroneb (G.2.6), dicloran (G.2.1), etridiazole (G.2.7), quintozene (G.2.2), tecnazene (G.2.3), tolclofos-methyl (G.2.4);

[1182] - cell membrane permeability (F4): propamocarb (G.4.1);

[1183] - ergosterol binding (F8): natamycin;

[1184] - oxysterol binding protein (F9): fluoxapiprolin (G.5.3), oxathiapiprolin (G.5.1), 4-[1-[2-[3-(di- fluoromethyl)-5-methyl-pyrazol-1-yl]acetyl]-4-piperidyl]- / V-tetralin-1-yl-pyridine-2-carboxamide (G.5.4), 4-[1 -[2-[3,5-bis(difluoromethyl)pyrazol-1 -yl]acetyl]-4-piperidyl]- / V-tetralin-1 -yl-pyri- dine-2-carboxamide (G.5.5), 4-[1-[2-[3-(difluoromethyl)-5-(trifluoromethyl)pyrazol-1-yl]acetyl]- 4-piperidyl]- / V-tetralin-1-yl-pyridine-2-carboxamide (G.5.6), 4-[1-[2-[5-cyclopropyl-3-(difluoro- methyl)pyrazol-1-yl]acetyl]-4-piperidyl]- / V-tetralin-1-yl-pyridine-2-carboxamide (G.5.7), 4-[1-[2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]- / V-tetralin-1-yl-pyridine- 2-carboxamide (G.5.8), 4-[1-[2-[5-(difluoromethyl)-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-pi- peridyl]- / V-tetralin-1-yl-pyridine-2-carboxamide (G.5.9), 4-[1-[2-[3,5-bis(trifluoromethyl)pyr- azol-1-yl]acetyl]-4-piperidyl]- / V-tetralin-1-yl-pyridine-2-carboxamide (G.5.10), (4-[1-[2-[5-cy- clopropyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]- / V-tetralin-1-yl-pyridine-2-carbox- amide (G.5.11), (1-(4-(4-(5-(2,6-dichlorophenyl)-4,5-dihydroisoxazol-3-yl)thiazol-2-yl)piper- idin-1-yl)-2-((3-trifluoromethyl)pyrazin-2-yl)oxy)ethan-1-one, 1-(4-(4-(5-(2-chloro-6-fluoro- phenyl)-4,5-dihydroisoxazol-3-yl)thiazol-2-yl)piperidin-1-yl)-2-((3-trifluoromethyl)pyridin-2-yl)- oxy)ethan-1-one, tert-butyl 4-(4-(5-(2-bromo-6-fluorophenyl)-4,5-dihydroisoxazol-3-yl)thiazol- 2-yl)piperidin-1 -carboxylate, ((2-(3-(2-(1-(2-(3,5-bis(trifluoromethyl)-1 H-pyrazol-1 -yl)acetyl)- piperidin-4-yl)thiazol-4-yl)-4,5-dihydroisoxazo-5-yl)-3-fluorophenyl)imino)dimethyl-A6-sulfa- none, ((2-(3-(2-(1-(2-(3,5-bis(difluoromethyl)-1 / - / -pyrazol-1-yl)acetyl)piperidin-4-yl)thiazol- 4-yl)-4,5-dihydroisoxazo-5-yl)-3-fluorophenyl)imino)dimethyl-A6-sulfanone,

[1185] ((2-(3-(2-(1 -(2-(3,5-bis(difluoromethyl)-1 H-pyrazol-1 -yl)acetyl)piperidin-4-yl)thiazol-4-yl)- 4,5-dihydroisoxazo-5-yl)-3-chorophenyl)imino)(isopropyl)(methyl)-A6-sulfanone,

[1186] ((2-(3-(2-(1-(2-(3,5-bis(trifluoromethyl)-1 H-pyrazol-1 -yl)acetyl)piperidin-4-yl)thiazol-4-yl)-250444W001

[1187] 106

[1188] 4.5-dihydroisoxazo-5-yl)-3-fluorophenyl)imino)(isopropyl)(methyl)-A6-sulfanone,

[1189] ((2-(3-(2-(1 -(2-(3,5-bis(difluoromethyl)-1 H-pyrazol-1 -yl)acetyl)piperidin-4-yl)thiazol-4-yl)- 4.5-dihydroisoxazo-5-yl)-3-(trifluoromethyl)phenyl)imino)dimethyl-A6-sulfanone, ((3-fluoro- 2-(3-(2-(1-(2-(5-methyl-3-(trifluoromethyl)-1 H-pyrazol-1 -yl)acetyl)piperidin-4-yl)thiazol-4-yl)- 4.5-dihydroisoxazo-5-yl)-phenyl)imino)dimethyl-A6-sulfanone;

[1190] H) Multi Site Activity (M)

[1191] - inorganics (M01): Bordeaux mixture (H.1.1), copper (H.1.2), copper acetate (H.1.3), copper hydroxide (H.1.4), copper oxychloride (H.1.5), basic copper sulfate (H.1.6), sulfur (H.1.7); - dithiocarbamates and relatives: ferbam (H.2.1), mancozeb (H.2.2), maneb (H.2.3), metam (H.2.4), metiram (H.2.5), propineb (H.2.6), thiram (H.2.7), zineb (H.2.8), ziram (H.2.9), zinc thiazole (H.2.10);

[1192] - organochlorine compounds (M04, M05, M06, M08): anilazine (H.3.1), captafol (H.3.3), captan (H.3.4), chlorothalonil (H.3.2), dichlofluanid (H.3.6), dichlorophen (H.3.7), folpet (H.3.5), hexachlorobenzene (H.3.8), pentachlorphenole (H.3.9) and its salts, phthalide (H.3.10), tolylfluanid (H.3.11);

[1193] - guanidines, quinones, quinoxalines, maleimides, thiocarbamates (M07, M09, M10, M11, M12): chinomethionat (H.4.13), dithianon (H.4.9), fluoroimide (H.4.11), guanidine (H.4.1), guazatine (H.4.4), guazatine-acetate (H.4.5), iminoctadine (H.4.6), iminoctadine-triacetate (H.4.7), iminoctadine-tris(albesilate) (H.4.8), methasulfocarb (H.4.12), 2,6-dimethyl- 1H,5H-[1,4]dithiino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetraone (H.4.10),

[1194] I) Cell wall biosynthesis (H) and melanin synthesis in cell wall (I)

[1195] - chitin synthase (H4): polyoxin B (1.1.2);

[1196] - cellulose synthase (H5): benthiavalicarb (1.3.5), dimethomorph (1.3.1), flumorph (1.3.2), iprovalicarb (1.3.6), mandipropamid (1.3.3), pyrimorph (1.3.4), valifenalate (1.3.7);

[1197] - reductase in melanin synthesis (MBI-R; 11) pyroquilon (1.2.1), tricyclazole (1.2.2);

[1198] - dehydratase in melanin synthesis (MBI-D, I2); carpropamid (1.2.3), dicyclomet (1.2.4), fenoxanil (1.2.5);

[1199] - polyketide synthase in melanin synthesis (MBI-P, I3): tolprocarb (1.2.6);

[1200] J) Plant defence induction (P1 to P8)

[1201] - salicylate-related (P01-P03, P08): acibenzolar-S-methyl (J.1.1), probenazole (J.1.2), isotianil (J.1.3), tiadinil (J.1.4), dichlobentiazox (J.1.13); phosphonates (P07): fosetyl (J.1.6), fosetyl- aluminum (J.1.7), phosphorous acid and its salts (J.1.8), calcium phosphonate (J.1.11), potassium phosphonate (J.1.12); others: potassium or sodium bicarbonate (J.1.9), 4-cyclo- propyl- / V-(2,4-di-,methoxy-,phenyl)thiadiazole-5-carboxamide (J.1.10);

[1202] K) Unknown mode of action (U)

[1203] - aminopyrifen (K.1.54), benziothiazolinone (K.1.48), bromothalonil (K.1.49), bronopol (K.1.1), cyflufenamid (K.1.3), cymoxanil (K.1.4), dazomet (K.1.5), debacarb (K.1.6), diclomezine (K.1.8), difenzoquat (K.1.9), difenzoquat-methylsulfate (K.1.10), diphenylamin (K.1.11), dodine, dodine free base (K.1.18), fenitropan (K.1.12), flufenoxadiazam (K.1.58) [MoA250444W001

[1204] 107

[1205] proposed: class II histone deacetylase inhibitor], flumetover (K.1.14), flumetylsulforim (K.1.60), flusulfamide (K.1.15), flutianil (K.1.16), harpin (K.1.17), nitrapyrin (K.1.19), nitrothal-isopropyl (K.1.20), oxine-copper (K.1.22), picarbutrazox (K.1.41), pyrisoxazole (K.1.37), seboctylamine (K.1.61), tebufloquin (K.1.24), tecloftalam (K.1.25), triazoxide (K.1.26), validamycin (K.1.2); / V-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)- / V-ethyl- / V-methyl formamidine (K.1.27), / V-(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)- / V-ethyl- / V-methyl formamidine (K.1.28), / V-[4-[[3-[(4-chlorophenyl)methyl]-1,2,4-thia-diazol-5-yl]oxy]-2,5-dimethyl-phenyl]- / V-ethyl- / V-methyl-formamidine (K.1.29), / V-(5-bromo-6-indan-2-yloxy-2-methyl-3-pyridyl)- / V-ethyl- / V-methyl-formamidine (K.1.30), / V-[5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methyl-3-pyridyl]- / V-ethyl- / V-methyl-formamidine (K.1.31), / V-[5-bromo-6-(4-isopropylcyclohexoxy)-2-methyl-3-pyridyl]- / V-ethyl- / V-methyl-formamidine (K.1.32), / V-[5-bromo-2-methyl-6-(1-phenylethoxy)-3-pyridyl]- / V-ethyl- / V-methyl-formamidine (K.1.33), / V-(2-methyl-5-trifluoromethyl-4-(3-trimethylsilanyl-propoxy)-phenyl)- / V-ethyl- / V-methyl formamidine (K.1.34), / V-(5-difluoromethyl-2-methyl-4-(3-trimethylsilanyl-propoxy)-phenyl)- / V-ethyl- / V-methyl formamidine (K.1.35), 2-(4-chloro-phenyl)- / V-[4-(3,4-dimethoxy-phenyl)-isoxazol-5-yl]-2-prop-2-ynyloxy-acetamide (K.1.36), 3-[5-(4-methylphenyl)-2,3-di-methyl-isoxazolidin-3-yl]-pyridine (K.1.38), 5-chloro-1-(4,6-dimethoxy-pyrimidin-2-yl)-2-meth-yl-1H-benzoimidazole (K.1.39), ethyl (Z)-3-amino-2-cyano-3-phenyl-prop-2-enoate (K.1.40), pentyl / V-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carba-mate (K.1.42), but-3-ynyl / V-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxy-methyl]-2-pyridyl]carbamate (K.1.43), 2-(6-benzyl-2-pyridyl)quinazoline (K.1.50), 2-[6-(3-flu-oro-4-methoxy-phenyl)-5-methyl-2-pyridyl]quinazoline (K.1.51), / V-(2,5-dimethyl-4-phenoxy-phenyl)- / V-ethyl- / V-methyl-formamidine (K.1.53), / V-[5-bromo-2-methyl-6-(1-methyl-2-prop-oxy-ethoxy)-3-pyridyl]- / V-ethyl- / V-methyl-formamidine (K.1.56), / V'-[4-(4,5-dichlorothiazol-2-yl)oxy-2,5-dimethyl-phenyl]- / V-ethyl- / V-methyl-formamidine (K.1.57), / V-methyl-4-[5-(tri-fluoromethyl)-1 ,2,4-oxadiazol-3-yl]benzenecarbothioamide (K.1.59), / V-methoxy- / V-[[4-[5-(tri-fluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide (K.1.61), / V-((4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl)methyl)propanamide (K.1.62), 3,3,3-tri-fluoro- / V-[[3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide (K.1.63), 3,3,3-trifluoro- / V-[[2-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-propanamide (K.1.64), / V-[2,3-difluoro-4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]benzyl]-butanamide (K.1.65), / V-[[2,3-difluoro-4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]-methyl]-3,3,3-trifluoro-propanamide (K.1.66), 1-methoxy-1-methyl-3-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]urea (K.1.67), 1 , 1 -diethyl-3-[[4-[5-[trifluoromethyl]- 1.2.4-oxadiazol-3-yl]phenyl]methyl]urea (K.1.68), / V,2-dimethoxy- / V-[[4-[5-(trifluoromethyl)- 1.2.4-oxadiazol-3-yl]phenyl]methyl]propanamide (K.1.69), / V-ethyl-2-methyl- / V-[[4-[5-(trifluoro-methyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide (K.1.70), 1-methoxy-3-methyl- 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea (K.1.71), 1-[[4-[5-(trifluoro-methyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-one (K.1.72), 1-[[4-[5-(trifluoro-methyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]piperidin-2-one (K.1.73), 4-[[4-[5-(trifluoromethyl)- 1.2.4-oxadiazol-3-yl]phenyl]methyl]morpholin-3-one (K.1.74), 4,4-dimethyl-2-[[4-[5-(trifluoro-methyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one (K.1.75), 2-[[4-[5-(trifluoro-methyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one (K.1.76), 5,5-dimethyl- 2-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one (K.1.77), 3,3-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]piperidin-2-one250444W001

[1206] 108

[1207] (K.1.78), 2-[[4-[5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl]phenyl]methyl]oxazinan-3-one (K.1.79), 1-[[3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]azepan-2-one (K.1.80), 4,4-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidin- 2-one (K.1.81), 5-methyl-1-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]-pyrrolidin-2-one (K.1.82), ethyl 1-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]-pyrazole-4-carboxylate (K.1.83), / V-methyl-1-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]-phenyl]methyl]pyrazole-4-carboxamide (K.1.84), / V, / V-dimethyl-1-[4-[5-(trifluoromethyl)- 1.2.4-oxadiazol-3-yl]benzyl]-1 H-1 ,2,4-triazol-3-amine (K.1.85), / V-methoxy- / V-methyl- 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxamide (K.1.86), propyl-1-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole- 4-carboxamide (K.1.87), / V-methoxy-1-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]-methyl]pyrazole-4-carboxamide (K.1.88), / V-allyl- / V-[[4-[5-(trifluoromethyl)- 1 ,2,4-oxadiazol- 3-yl]phenyl]methyl]propanamide (K.1.89), 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)- 1.2.4-oxadiazol-3-yl]phenyl]methyl]urea (K.1.90), 1 ,3-dimethoxy-1-[[4-[5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl]phenyl]methyl]urea (K.1.91), / V-allyl- / V-[[4-[5-(trifluoromethyl)-1 ,2,4-oxa-diazol-3-yl]phenyl]methyl]acetamide (K.1.92), / V-[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]-benzyl]cyclopropanecarboxamide (K.1.93), 1-methyl-3-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadi-azol-3-yl]phenyl]methyl]urea (K.1.94), / V'-[2-chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]- / V-ethyl- / V-methyl-formamidine (K.1.95), / V-[2-chloro-4-[(4-methoxy-phenyl)methyl]-5-methyl-phenyl]- / V-ethyl- / V-methyl-formamidine (K.1.96), / V'-[2-chloro-4-[(4-cyano-phenyl)methyl]- 5-methyl-phenyl]- / V-ethyl- / V-methyl-formamidine (K.1.97), / V'-[2,5-dimethyl-4-(o-tolylmethyl)-phenyl]- / V-ethyl-N-methyl-formamidine (K.1.98), 6-chloro-3-(3-cyclopropyl-2-fluoro-phenoxy)- / V-[2-(2,4-dimethylphenyl)-2,2-difluoro-ethyl]-5-methyl-pyridazine-4-carboxamide (K.1.99), 3-(3-bromo-2-fluoro-phenoxy)-6-chloro- / V-[2-(2-chloro-4-methyl-phenyl)-2,2-difluoro-ethyl]-5-methyl-pyridazine-4-carboxamide (K.1.100), 6-chloro- / V-[2-(2-chloro-4-methyl-phenyl)-2,2-difluoro-ethyl]-3-(3-cyclopropyl-2-fluoro-phenoxy)-5-methyl-pyridazine-4-carboxamide (K.1.101), 6-chloro-3-(3-cyclopropyl-2-fluoro-phenoxy)- / V-[2-(3,4-dimethylphenyl)-2,2-diflu-oro-ethyl]-5-methyl-pyridazine-4-carboxamide (K.1.102), 6-chloro-3-(3-chloro-2-fluoro-phen-oxy)- / V-[2-(2,4-dimethylphenyl)-2,2-difluoro-ethyl]-5-methyl-pyridazine-4-carboxamide (K.1.103), / V-[2-(2-bromo-4-methyl-phenyl)-2,2-difluoro-ethyl]-6-chloro-3-(3-cyclopropyl-2-flu-oro-phenoxy)-5-methyl-pyridazine-4-carboxamide (K.1.104), 2-[cyano-(2,6-difluoro-4-pyri-dyl)amino]-5-methyl- / V-spiro[3.4]octan-3-yl-thiazole-4-carboxamide, 2-[acetyl-(2,6-difluoro- 4-pyridyl)amino]- / V-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide, 2-[(2,6-di-fluoro-4-pyridyl)-(2-methoxyacetyl)amino]- / V-(2,2-dimethylcyclobutyl)-5-methyl-thiazole- 4-carboxamide, 2-[cyano-(2,6-difluoro-4-pyridyl)amino]- / V-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide, / V-[1-[[3 2-(5-fluoro-2-methoxy-phenyl)-2-hydroxy-ethyl]- 5-[(Z)- / V-isopropoxy-C-methyl-carbonimidoyl]-2,6-dioxo-pyrimidin-1-yl]methyl]-2-methyl-propyl]-2-methyl-propanamide, / V-[1-[[3-[2-(5-fluoro-2-methoxy-phenyl)-2-hydroxy-ethyl]-5-[(Z)- / V-isopropoxy-C-methyl-carbonimidoyl]-2,6-dioxo-pyrimidin-1-yl]methyl]-2-methyl-propyl]-2,2-dimethyl-propanamide, / V-[2-[3-[2-(5-fluoro-2-methoxy-phenyl)-2-hydroxy-ethyl]-5-[(Z)- / V-isopropoxy-C-methyl-carbonimidoyl]-2,6-dioxo-pyrimidin-1-yl]-1-methyl-ethyl]- 2-methyl-propanamide, / V-[2-[3-[2-hydroxy-2-(2-methoxyphenyl)ethyl]-5-[(Z)- / V-isopropoxy-C-methyl-carbonimidoyl]-2,6-dioxo-pyrimidin-1-yl]-1-methyl-ethyl]-2-methyl-propanamide, / V-[2-[3-[2-(2-cyanoethoxy)-2-(5-fluoro-2-methoxy-phenyl)ethyl]-5-[(Z)- / V-isopropoxy-C-meth-yl-carbonimidoyl]-2,6-dioxo-pyrimidin-1-yl]-1-methyl-ethyl]-2-methyl-propanamide,250444W001

[1208] 109

[1209] rac-3-[3-(3-chloro-2-fluoro-phenoxy)-6-methyl-pyridazin-4-yl]-5-[(2-chloro-4-methyl-phenyl)- methyl]-5,6-dihydro-4H-1,2,4-oxadiazine, (5S)-3-[3-(3-chloro-2-fluoro-phenoxy)-6-methyl- pyridazin-4-yl]-5-[(2-chloro-4-methyl-phenyl)methyl]-5,6-dihydro-4 / - / -1,2,4-oxadiazine, (5R)-3-[3-(3-chloro-2-fluoro-phenoxy)-6-methyl-pyridazin-4-yl]-5-[(2-chloro-4-methyl-phenyl)- methyl]-5,6-dihydro-4H-1,2,4-oxadiazine, 2-(4-fluorophenoxy)-1-[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]ethanone, 2-[(6-fluoro-3-pyridyl)oxy]-1-[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]ethanone, 2-(4-fluoroanilino)-1-[4-[5-(trifluoromethyl)-1,2,4-oxa- diazol-3-yl]phenyl]ethenone, ethyl 1-[[4-[[2-(trifluoromethyl)-1 ,3-dioxolan-2-yl]methoxy]- phenyl]methyl]-1H-pyrazole-4-carboxylate, ethyl 1 -[[4-[[(1 Z)-2-ethoxy-3, 3, 3-trifluoro-1 -pro- pen-1 -yl]oxy]phenyl]methyl]-1H-pyrazole-4-carboxylate;

[1210] L) Biopesticides

[1211] L1) Microbial pesticides with fungicidal, bactericidal, viricidal and / or plant defense activator activity: Ampelomyces quisqualis, Aspergillus flavus, Aureobasidium pullulans, Bacillus altitudinis, B. amyloliquefaciens, B. amyloliquefaciens ssp. plantarum (also referred to as B. velezensis), B. megaterium, B. mojavensis, B. mycoides, B. pumilus, B. simplex, B. solisalsi, B. subtilis, B. subtilis var. amyloliquefaciens, B. velezensis, Candida oleo- phila, C. saitoana, Clavibacter michiganensis (bacteriophages), Coniothyrium minitans, Cryphonectria parasitica, Cryptococcus albidus, Dilophosphora alopecuri, Fusarium oxysporum, Clonostachys rosea f. catenulate (also named GHocladium catenulatum), GHocladium roseum, Lysobacter antibioticus, L. enzymogenes, Metschnikowia fructi- cola, Microdochium dimerum, Microsphaeropsis ochracea, Muscodor albus, Paeni- bacillus alvei, Paenibacillus epiphyticus, P. polymyxa, Pantoea vagans, Penicillium bilaiae, Phlebiopsis gigantea, Pseudomonas sp., Pseudomonas chloraphis, Pseudo- zyma flocculosa, Pichia anomala, Pythium oligandrum, Sphaerodes mycoparasitica, Streptomyces griseoviridis, S. lydicus, S. violaceusniger, Talaromyces flavus, Tricho- derma asperelloides, T. asperellum, T. atroviride, T. fertile, T. gamsii, T. harmatum, T. harzianum, T. polysporum, T. stromaticum, T. virens, T. viride, Typhula phacorrhiza, Ulocladium oudemansii, Verticillium dahliae, zucchini yellow mosaic virus (avirulent strain);

[1212] L2) Biochemical pesticides with fungicidal, bactericidal, viricidal and / or plant defense activator activity: harpin protein, plant oils (BM3): tea tree oil, orange oil (L.2.1), eugenol, limonene (L.2.2), geraniol (L.2.3), thymol (L.2.4); Reynoutria sachalinensis extract, aureobasidin (in particular aureobasidin A (L.2.5)), ambruticin (L.2.6), bafilomycin (L.2.7) (in particular bafilomycin A1, B1 and C1), chlorflavonin (L.2.8), cinnamaldehyde (L.2.9), natamycin (L.2.10; F8);

[1213] L3) Microbial pesticides with insecticidal, acaricidal, molluscidal and / or nematicidal activity:

[1214] Agrobacterium radiobacter, Bacillus cereus, B. firmus, B. thuringiensis, B. thuringiensis ssp. aizawai, B. t. ssp. israelensis, B. t. ssp. galleriae, B. t. ssp. kurstaki, B. t. ssp. tene- brionis, Beauveria bassiana, B. brongniartii, Burkholderia spp., Chromobacterium sub- tsugae, Cydia pomonella granulovirus (CpGV), Cryptophlebia leucotreta granulovirus (CrleGV), Flavobacterium spp., Helicoverpa armigera nucleopolyhedrovirus (HearNPV), Helicoverpa zea nucleopolyhedrovirus (HzNPV), Helicoverpa zea single250444W001

[1215] 110

[1216] capsid nucleopolyhedrovirus (HzSNPV), Heterorhabditis bacteriophora, Isaria fumoso- rosea, Lecanicillium longisporum, L. muscarium, Metarhizium anisopliae, M. anisopliae var. anisopliae, M. anisopliae var. acridum, Nomuraea rileyi, Paecilomyces fumoso- roseus, P. lilacinus, Paenibacillus popilliae, Pasteuria spp., P. nishizawae, P. penetrans, P. ramosa, P. thornea, P. usgae, Pseudomonas fluorescens, Spodoptera Htto- ralis nucleopolyhedrovirus (SpliNPV), Steinernema carpocapsae, S. feltiae, S. kraussei, Streptomyces galbus, S. microflavus- L4) Biochemical pesticides with insecticidal, acaricidal, molluscidal, pheromone and / or nematicidal activity: L-carvone, citral, (E,Z)-7,9-dodecadien-1-yl acetate, ethyl formate, (E,Z)-2,4-ethyl decadienoate (pear ester), (Z,Z,E)-7,11,13-hexadecatrienal, heptyl butyrate, isopropyl myristate, lavanulyl senecioate, cis-jasmone, 2-methyl-1 -butanol, methyl eugenol, methyl jasmonate, (E,Z)-2,13-octadecadien-1-ol, (E,Z)-2,13-octadecadien-1-ol acetate, (E,Z)-3,13-octadecadien-1-ol, (R)-1-octen-3-ol, pentatermanone,

[1217] (E,Z,Z)-3,8,11-tetradecatrienyl acetate, (Z,E)-9,12-tetradecadien-1-yl acetate,

[1218] (Z)-7-tetradecen-2-one, (Z)-9-tetradecen-1-yl acetate, (Z)-11-tetradecenal, (Z)-11-tetra- decen-1-ol, extract of Chenopodium ambrosiodes, Neem oil, Quillay extract;

[1219] L5) Microbial pesticides with plant stress reducing, plant growth regulator, plant growth promoting and / or yield enhancing activity: Azospirillum amazonense, A. brasilense, A. lipoferum, A. irakense, A. halopraeferens, Bradyrhizobium spp., B. elkanii, B.japoni- cum, B. liaoningense, B. lupini, Delftia acidovorans, Glomus intraradices, Mesorhizo- bium spp., Rhizobium leguminosarum bv. phaseoli, R. I. bv. trifolii, R. I. bv. viciae, R. tropic!, Sinorhizobium melilotr',

[1220] O) Insecticides from classes O.1 to 0.29, and O.UN (IRAC classes 1 to 37, and UN (incl. UNA to UNV)):

[1221] 0.1 Acetylcholine esterase (AChE) inhibitors: carbamates (1A): aldicarb, alanycarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC, xylylcarb; organophosphates (1B): acephate, azamethiphos, azinphos-ethyl, azinphosmethyl, cadusa- fos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, couma- phos, cyanophos, demeton-S-methyl, diazinon, dichlorvos, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl □-(methoxyaminothio- phosphoryl) salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion- methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos- methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon, vamidothion;

[1222] 0.2 GABA-gated chloride channel blockers: (2A): chlordane, endosulfan; (2B): ethiprole, fipronil, flufiprole, nicofluprole, pyrafluprole, pyriprole;

[1223] 0.3 Sodium channel modulators: pyrethroids (3A): acrinathrin, allethrin, d-cis-trans allethrin,250444W001

[1224] 111

[1225] d-trans allethrin, bifenthrin, kappa-bifenthrin, bioallethrin, bioallethrin S-cylclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin, befa-cyfluthrin, cyhalothrin, / ambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, a / pba-cypermethrin, befa-cypermethrin, theta-cyper- methrin, zeta-cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, fau-fluvalinate, halfenprox, heptafluthrin, imiprothrin, meperfluthrin, metofluthrin, momfluorothrin, epsilon-mom- fluorothrin, permethrin, phenothrin, prallethrin, profluthrin, pyrethrins (pyrethrum), resmethrin, silafluofen, tefluthrin, kappa-tefluthrin, tetramethylfluthrin, tetramethrin, tralomethrin, trans- fluthrin; (3B): DDT, methoxychlor;

[1226] 0.4 Nicotinic acetylcholine receptor (nAChR) competitive modulators: neonicotinoids (4A): acetamiprid, clothianidin, cycloxaprid, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam; 4,5-dihydro- / V-nitro-1-(2-oxiranylmethyl)-1 / - / -imidazol-2-amine,

[1227] (2E)-1-[(6-chloropyridin-3-yl)methyl]- / V-nitro-2-pentylidenehydrazinecarboximidamide;

[1228] 1-[(6-chloropyridin-3-yl)methyl]-7-methyl-8-nitro-5-propoxy- 1,2, 3,5,6, 7-hexahydroimid- azo[1,2-a]pyridine; (4B) nicotine; sufoximines (4C): sulfoxaflor; butenolindes (4D): flupyradifurone; mesionics (4E): dicloromezotiaz, fenmezoditiaz, triflumezopyrim, pyridyl- idenes (4F): flupyrimin, 1-[(2-chlorothiazol-5-yl)methyl]-3-(3,5-dimethylisoxazol-4-yl)- pyrido[1,2-a]pyrimidine-2, 4-dione;

[1229] 0.5 nAChR allosteric modulators: spinetoram, spinosad;

[1230] 0.6 Glutamate gated chloride channel allosteric modulators: abamectin, emamectin benzoate, ivermectin, lepimectin, milbemectin;

[1231] 0.7 Juvenile hormone receptor modulators: hormone analogs (7 A): hydroprene, kinoprene, methoprene; fenoxycarb (7B), pyriproxyfen (7C);

[1232] 0.8 miscellaneous non-specific (multi-site) inhibitors: methyl bromide and other alkyl halides; chloropicrin, cryolite, sulfuryl fluoride, borax, tartar emetic;

[1233] 0.9 Chordotonal organ TRPV channel modulators: afidopyropen, pymetrozine, pyrifluquinazon; 0.10 Mite growth inhibitors: clofentezine, diflovidazin, hexythiazox; etoxazole;

[1234] 0.11 Microbial disruptors of midgut membranes: Bacillus thuringiensis subsp. israelensis, B. t.

[1235] subsp. aizawai, B. t. subsp. kurstaki, B. t. subsp. tenebrionis, B. sphaericus: B.t. crop proteins: CrylAb, CrylAc, CrylFa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34 / 35Ab1;

[1236] 0.12 Inhibitors of mitochondrial ATP synthase: diafenthiuron; azocyclotin, cyhexatin, fenbutatin oxide, propargite, tetradifon;

[1237] 0.13 Uncouplers of oxidative phosphorylation via disruption of the proton gradient: chlorfenapyr, DNOC, sulfluramid;

[1238] 0.14 nAChR channel blockers: bensultap, cartap hydrochloride, thiocyclam, thiosultap-sodium; 0.15 Inhibitors of the chitin biosynthesis CHS1: bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron;

[1239] 0.16 Inhibitors of the chitin biosynthesis type 1: buprofezin;250444W001

[1240] 112

[1241] 0.17 Moulting disruptors: cyromazine;

[1242] 0.18 Ecdyson receptor agonists: methoxyfenozide, tebufenozide, halofenozide, fufenozide, chromafenozide;

[1243] 0.19 Octopamin receptor agonists: amitraz;

[1244] 0.20 Mitochondrial complex III electron transport inhibitors - Qo site: hydramethylnon, acequinocyl, fluacrypyrim, flupyroxystrobin, bifenazate;

[1245] 0.21 Mitochondrial complex I electron transport inhibitors: fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad; rotenone;

[1246] 0.22 Voltage-dependent sodium channel blockers: indoxacarb, metaflumizone, / V-(3-chloro- 2-methylphenyl)-2-[(4-chlorophenyl)-[4-[methyl(methylsulfonyl)amino]phenyl]methylene]- hydrazinecarboxamide, / V-[4-chloro-2-[[(1 , 1 -dimethylethyl)amino]carbonyl]-6-methylphenyl]- 1-(3-chloro-2-pyridinyl)-3-(fluoromethoxy)-1 / - / -pyrazole-5-carboxamide, 2-[2-(4-cyanophenyl)- 1-[3-(trifluoromethyl)phenyl]ethylidene]- / V-[4-(difluoromethoxy)phenyl]- hydrazinecarboxamide;

[1247] 0.23 Inhibitors of the of acetyl CoA carboxylase: spidoxamat, spirodiclofen, spiromesifen, spirotetramat, spiropidion, spirobudifen, 11-(4-chloro-2,6-dimethylphenyl)-12-hydroxy- 1,4-dioxa-9-azadispiro[4.2.4.2]tetradec-11-en-10-one;

[1248] 0.24 Mitochondrial complex IV electron transport inhibitors: aluminium phosphide, calcium phosphide, phosphine, zinc phosphide, cyanide;

[1249] 0.25 Mitochondrial complex II electron transport inhibitors: cyclobutrifluram, cyenopyrafen, cyflumetofen, cyetpyrafen, pyflubumide;

[1250] 0.28 Ryanodine receptor-modulators: chlorantraniliprole, cyantraniliprole, cyclaniliprole, cyhalodiamide, flubendiamide, pixoaniliprole, fluchlodiniliprole, tetrachlorantraniliprole, tetraniliprole, tiorantraniliprole, (R)-3-chloro- / V1-{2-methyl-4-[1 ,2,2,2 -tetrafluoro-1-(trifluoro- methyl)ethyl]phenyl}- / \ / 2-(1-methyl-2-methylsulfonylethyl)phthalamide, (S)-3-chloro- / V1-{2-methyl-4-[1 , 2,2, 2-tetrafluoro-1 -(trifluoromethyl) ethyl]phenyl}-A / 2-(1 -methyl-2-meth- ylsulfonylethyl)phthalamide, methyl-2-[3,5-dibromo-2-({[3-bromo-1-(3-chloropyridin-2-yl)- 1 / - / -pyrazol-5-yl]carbonyl}amino)benzoyl]-1,2-dimethylhydrazinecarboxylate; / V-[4,6-dichloro- 2-[(diethyl- / ambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoro- methyl)pyrazole-3-carboxamide; / V-[4-chloro-2-[(diethyl- / ambda-4-sulfanylidene)carbamoyl]- 6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;

[1251] / V-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloro- 2-pyridinyl)-1H-pyrazole-5-carboxamide; 3-chloro-1-(3-chloro-2-pyridinyl)- / V-[2,4-dichloro- 6-[[(1-cyano-1-methylethyl)amino]carbonyl]phenyl]-1 / - / -pyrazole-5-carboxamide; / V-[4-chloro- 2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridinyl)-3-(fluoro- methoxy)-1H-pyrazole-5-carboxamide; / V-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-meth- ylphenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1 / - / -pyrazole-5-carboxamide;

[1252] 0.29 Chordotonal organ modulators: flonicamid, flumetnicam;

[1253] 0.30 GABA-gated chloride channel allosteric modulators: broflanilide, cyproflanilide, fluralaner, fluxametamide, isocycloseram, lotilaner, piperflanilide, sarolaner, tigolaner, umifoxolaner;250444W001

[1254] 113

[1255] 0.33 Calcium-activated potassium channel modulators: acynonapyr;

[1256] 0.34 Mitochondrial complex III electron transport inhibitors - Qi site: flometoquin;

[1257] 0.35 RNA interference mediated target suppressors: ledprona, vadescana;

[1258] 0.36: Chordotonal organ modulators: dimpropyridaz;

[1259] 0.37: Vesicular AchT inhibitors: cybenzoxasulfyl, oxazosulfyl;

[1260] O.UN Unknown or uncertain mode of action: afoxolaner, azadirachtin, amidoflumet, bentioflumin, benzoximate, benzpyrimoxan, bromopropylate, bisulfufen, chinomethionat, dicofol, fluazaindolizine, flufenerim, fluensulfone, fluhexafon, flupentiofenox, galquin, indazapyroxamet, isoflualanam, metaldehyde, metoxadiazone, piperonyl butoxide, pyridalyl, sulfiflumin, tiapyrachlor, tioxazafen, trifluenfuronate, tyclopyrazoflor; 11-(4-chloro- 2,6-dimethylphenyl)-12-hydroxy-1,4-dioxa-9-azadispiro[4.2.4.2]-tetradec-11-en-10-one, 3-(4’-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]dec-3-en-2-one, 1 -[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3-(trifluoromethyl)-1 H-1 ,2,4-tri- azole-5-amine, / V-[5-[[2-bromo-6-chloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)-propyl]- phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; 4-cyano- / V-[2-cyano- 5-[[2,6-dichloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)-propyl]phenyl]carbamoyl]phe- nyl]-2-methyl-benzamide; 4-cyano- / V-[2-cyano-5-[[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(tri- fluorornethyl)ethyl]phenyl]carbamoyl]-,phenyl]-2-methyl-benzamide; / V- [5- [[2- bro mo-6- ch loro- 4 1 ,2,2, 2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]carba-,moyl]-2-cyano-phenyl]-4-cyano- 2-methyl-benzamide; 1-[(6-chloro-3-pyridinyl)methyl]- 1,2, 3,5,6, 7-hexahydro-5-methoxy- 7-methyl-8-nitro-imidazo[1 ,2-a]pyridine; 1 -[(6-chloropyridin-3-yl)methyl]-7-methyl-8-nitro- 1.2.3.5.6.7-hexahydroimidazo[1 ,2-a]pyridin-5-ol; 1-[(6-chloro-3-pyridinyl)methyl]- 1.2.3.5.6.7-hexahydro-5-methoxy-7-methyl-8-nitro-imidazo[1 ,2-a]pyridine; 2-(3-pyridinyl)- / V-(2-pyrimidinylmethyl)-2 / - / -indazole-5-carboxamide; / V-[4-chloro-3-[[(phenylmethyl)amino]- carbonyl]phenyl]-1-methyl-3-(1, 1,2,2, 2-pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole- 5-carboxamide; / V-[4-chloro-3-[[(phenylmethyl)amino]carbonyl]phenyl]-1-methyl- 3-(1 ,1 ,2,2,2-pentafluoroethyl)-4-(trifluoromethyl)-1 / - / -pyrazole-5-carboxamide; 2-(3-ethylsul- fonyl-2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 2-[3-ethylsulfonyl-5-(tri- fluoromethyl)-2-pyridyl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine; / V-[4-chloro-3-(cy- clopropylcarbamoyl)phenyl]-2-methyl-5-(1, 1,2,2, 2-pentafluoroethyl)-4-(trifluoromethyl)- pyrazole-3-carboxamide, / V-[4-chloro-3-[(1-cyanocyclopropyl)carbamoyl]phenyl]-2-methyl- 5-(1,1,2,2,2-pentafluoroethyl)-4-(trifluoromethyl)pyrazole-3-carboxamide;

[1261] [(2S,3R,4R,5S,6S)-3,5-dimethoxy-6-methyl-4-propoxy-tetrahydropyran-2-yl]- / V-[4-[1-[4-(tri- fluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]carbamate; [(2S,3R,4R,5S,6S)-3,4,5-trimeth- oxy-6-methyl-tetrahydropyran-2-yl]- / V-[4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]- phenyl]carbamate; [(2S,3R,4R,5S,6S)-3,5-dimethoxy-6-methyl-4-propoxy-tetrahydropyran- 2-yl]- / V-[4-[1-[4-(1 ,1 ,2,2,2-pentafluoroethoxy)phenyl]-1 ,2,4-triazol-3-yl]phenyl]carbamate; [(2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-yl]- / V-[4-[1 -[4-(1 , 1 ,2,2,2-pen- tafluoroethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]carbamate; (2Z)-3-(2-isopropylphenyl)- 2-[(E)-[4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]methylenehydrazono]- thiazolidin-4-one, (2Z)-3-(2-isopropylphenyl)-2-[(E)-[4-[1-[4-(1 ,1 ,2,2,2-pentafluoroethoxy)- phenyl]-1,2,4-triazol-3-yl]phenyl]methylenehydrazono]thiazolidin-4-one, (2Z)-3-(2-iso-250444W001

[1262] 114

[1263] pro-,pyhphenyl)-2-[(E)-[4-[1-[4-(1 ,1 ,2,2,2-pentafluoroethoxy)phenyl]-1 ,2,4-triazol-3-yl]- phenyl]methylenehydrazono]thiazolidin-4-one; 2-(6-chloro-3-ethylsulfonyl-imidazo[1,2-a]py- ridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 2-(6-bromo-3-ethylsulfonyl- imidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 2-(3-eth- ylsulfonyl-6-iodo-imidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyri- dine, 2-(7-chloro-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imid- azo[4,5-b]pyridine, 2-(7-chloro-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(tri- fluoromethyl)imidazo[4,5-b]pyridine, 2-(3-ethylsulfonyl-7-iodo-imidazo[1,2-a]pyridin-2-yl)- 3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 3-ethylsulfonyl-6-iodo-2-[3-methyl-6-(tri- fluoromethyl)imidazo[4,5-b]pyridin-2-yl]imidazo[1,2-a]pyridine-8-carbonitrile, 2-[3-ethyl- sulfonyl-8-fluoro-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl)- imidazo[4,5-b]pyridine, 2-[3-ethylsulfonyl-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]- 3-methyl-6-(trifluoromethylsulfinyl)imidazo[4,5-b]pyridine, 2-[3-ethylsulfonyl-7-(trifluoro- methyl)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine, 2-(6-bromo-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl)-6-(trifluoromethyl)pyrazolo[4,3-c]pyri- dine; / V-[[2-fluoro-4-[(2S,3S)-2-hydroxy-3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)pyrrolidin- 1-yl]phenyl]methyl]cyclopropanecarboxamide, / V-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-2-me- thylsulfonyl-propanamide, / V-[4-chloro-3-[(1-cyanocyclopropyl)carbamoyl]phenyl]-2-methyl- 4-methylsulfonyl-5-(1 ,1 ,2,2,2-pentafluoroethyl)pyrazole-3-carboxamide, 1 ,4-dimethyl- 2-[2-(pyridin-3-yl)-2 / - / -indazol-5-yl]-1, 2, 4-triazolidine-3, 5-dione, / V-[4-chloro-2-(3-pyridyl)thi- azol-5-yl]- / V-ethyl-3-methylsulfonyl-propanamide, / V-cyclopropyl-5-[(5S)-5-(3,5-dichloro- 4-fluoro-phenyl)-5-(trifluoromethyl)-4 / - / -isoxazol-3-yl]isoquinoline-8-carboxamide,

[1264] 5-[(5S)-5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4 / - / -isoxazol-3-yl]- / V-(pyrimidin- 2-ylmethyl)isoquinoline-8-carboxamide, / V-[1-(2,6-difluorophenyl)pyrazol-3-yl]-2-(trifluoro- methyl)benzamide, 5-((1R,3R)-3-(3,5-bis(trifluoromethyl)phenyl)-2,2-dichlorocyclopropane- 1-carboxamido)-2-chloro- / V-(3-(2,2-difluoroacetamido)-2,4-difluorophenyl)benzamide, 1-[6-(2,2-difluoro-7-methyl-[1,3]dioxolo[4,5-f]benzimidazol-6-yl)-5-ethylsulfonyl-3-pyridyl]- cyclopropanecarbonitrile, 6-(5-cyclopropyl-3-ethylsulfonyl-2-pyridyl)-2,2-difluoro-7-methyl- [1,3]dioxolo[4,5-f]benzimidazole, 3,5-bis(trifluoromethyl)- / V-[(1S)-1-[1-[6-(trifluoromethyl)- 4-pyrimidinyl]-1 / - / -1,2,4-triazol-5-yl]ethyl]-benzamide, 2-(3-ethylsulfonyl-2-pyridyl)- 5-(2,2,3,3,3-pentafluoropropoxy)pyrazine, 2-[3-ethylsulfonyl-6-(trifluoromethyl)pyrazolo- [1,5-a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 9-(methoxymethyl)- 5-(3-pyridyl)-2-oxa-5,6,9,14-tetrazatricyclo[8.4.0.0A{3,7}]tetradeca-1(10),3,6,11 ,13-pentaen- 8-one, 2-[5-[(E)-2-chloro-3,3,3-trifluoro-prop-1-enyl]-1-methyl-imidazol-2-yl]-5-cyclopropyl- 3-ethylsulfonyl-pyridine, (3Z)-1-[2-fluoro-4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]- phenyl]-3-[3-[5-methyl-2-(2,2,2-trifluoroethoxymethyl)phenyl]-4-oxo-thiazolidin-2-ylidene]- urea, 1 -[6-(2,2-difluoro-8-oxo-[1 ,3]dioxolo[4,5-g]chromen-7-yl)-5-ethylsulfonyl-3-pyridyl]- cyclopropanecarbonitrile, 2-chloro- / V-[(1S)-2-ethyl-1-methyl-butyl]furan-3-carboxamide, [5-cyclopropyl-2-[3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridin-2-yl]-3-pyridyl]-ethyl- hydroxy-oxo-A6-sulfane, 4-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4 / - / -isoxazol- 3-yl]-2-methyl- / V-[1-(2,2,2-trifluoroethylcarbamoyl)cyclopropyl]benzamide, 3-[3-ethylsulfonyl- 7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-7-(trifluoromethyl)chromen-4-one.

[1265] The active substances referred to as component 2) or 3) herein, their preparation and their activity e.g. against fungi is known (www.bcpcpesticidecompendium.bcpc.org / ); many of them250444W001

[1266] 115

[1267] are commercially available. Compounds defined by IUPAC nomenclature, their preparation and pesticidal activity are also known (e.g. Can. J. Plant Sci. 48(6), 587-94, 1968; EP-141 317; EP-152031; EP-226917; EP-243970; EP-256503; EP-428941; EP-532022; EP-1 028 125; EP-1 035 122; EP-1 201 648; EP-1 122244, JP2002316902; DE19650197; DE10021412; DE102005009458; 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 / 11853; 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 10 / 139271, WO 11 / 028657, WO 12 / 168188, WO 07 / 006670, WO 11 / 77514; WO 13 / 047749,

[1268] WO 10 / 069882, WO 13 / 047441, WO 03 / 16303, WO 09 / 90181, WO 13 / 007767, WO 13 / 010862, WO 13 / 127704, WO 13 / 024009, WO 13 / 24010, WO 13 / 047441, WO 13 / 162072,

[1269] WO 13 / 092224, WO 11 / 135833, CN 1907024, CN 1456054, CN 103387541, CN 1309897, WO 12 / 84812, CN 1907024, WO 09094442, WO 14 / 60177, WO 13 / 116251, WO 08 / 013622, WO 15 / 65922, WO 94 / 01546, EP 2865265, WO 07 / 129454, WO 12 / 165511, WO 11 / 081174, WO 13 / 47441, WO 16 / 156241, WO 16 / 162265, WO 23 / 99460, WO 21 / 244950, WO 21 / 244951, WO 22 / 130188, WO 22 / 243810, WO 21 / 255070, WO 21 / 176057, WO 21 / 153754, JP2023064110, JP2022153603, JP2022046550, JP2022031355, WO 22 / 249074,

[1270] WO 23 / 046861, WO 18 / 177894, WO 20 / 212513, WO 20 / 097012, WO 21 / 011722,

[1271] US 2023 / 0069915, WO 24 / 126388, WO 24 / 137594, EP4389739, WO 16 / 096584,

[1272] WO 24 / 120137, WO 24 / 188755, CN 115925576, WO 24 / 087613.According to the invention, the solid material (dry matter) of biopesticides (with exception of oils such as Neem oil) is considered as active component (e.g. to be obtained after drying or evaporation of the suspension medium in case of liquid formulations of microbial pesticides). The weight ratios and percentages used for a biological extract such as Quillay extract are based on the total weight of the dry content (solid material) of the respective extract(s).

[1273] The total weight ratios of compositions comprising at least one microbial pesticide in the form of viable microbial cells including dormant forms, can be determined using the amount of colony forming units (CFU) of the respective microorganism to calculate the total weight of the respective active component with the following equation that 1 x 1010CFU equals one gram of total weight of the respective active component. In addition, CFU may also be understood as the number of (juvenile) nematode individuals in case of nematode biopesticides, such as S. feltiae. In binary mixtures, the weight ratio of component 1) and component 2) (1 :2; w:w) generally depends from the properties of the components used, usually it is in the range of 1:10,000 to 10,000: 1 , often 1 : 100 to 100: 1 , regularly 1 :50 to 50: 1 , preferably 1 :20 to 20: 1 , more preferably from 1 : 10 to 10:1, even more preferably 1 :4 to 4: 1 , and in particular 1 :2 to 2: 1. According to further embodiments, the weight ratio of component 1) and component 2) (1 :2; w:w) usually is in the range of 1000: 1 to 1 : 1 , often 100: 1 to 1 : 1 , regularly 50: 1 to 1 : 1 , preferably 20: 1 to 1 : 1 , more preferably 10:1 to 1:1, even more preferably 4:1 to 1:1, and in particular 2:1 to 1:1. According to further embodiments, the weight ratio of component 1) and component 2) (1 :2; w:w) usually is in the range of 20,000: 1 to 1:10, often 10,000: 1 to 1:1, regularly 5,000: 1 to 5: 1 , preferably 5,000: 1 to 10:1, more preferably 2,000:1 to 30:1, even more preferably 2,000:1 to 100:1, and in particular 1,000:1 to 100:1. According to further embodiments, the weight ratio of component 1) and250444W001

[1274] 116

[1275] component 2) (1 :2; w:w) usually is in the range of 1 : 1 to 1:1000, often 1:1 to 1 : 100, regularly 1 : 1 to 1:50, preferably 1:1 to 1:20, more preferably 1:1 to 1:10, even more preferably 1:1 to 1:4, and in particular 1:1 to 1:2. According to further embodiments, the weight ratio of component 1) and component 2) (1 :2; w:w) usually is in the range of 10: 1 to 1 :20,000, often 1:1 to 1:10,000, regularly 1 :5 to 1 :5,000, preferably 1 : 10 to 1 :5,000, more preferably 1 :30 to 1 :2,000, even more preferably 1 : 100 to 1 :2,000, and in particular 1 : 100 to 1 : 1 ,000.

[1276] In ternary mixtures, i.e. compositions comprising the component 1) and component 2) and a compound III (component 3), the weight ratio of component 1) and component 2) (1 :2; w:w) depends from the properties of the active substances used, usually it is in the range of 1:100 to 100: 1 , regularly 1 :50 to 50: 1 , preferably 1 :20 to 20: 1 , more preferably 1 : 10 to 10: 1 , and in particular 1 :4 to 4:1 ; and the weight ratio of component 1) and component 3) (1 :3; w:w) usually is in the range of 1 : 100 to 100: 1 , regularly 1 :50 to 50: 1 , preferably 1 :20 to 20: 1 , more preferably 1:10 to 10:1, and in particular 1:4 to 4:1. Any further active components are, if desired, added in a ratio of 20:1 to 1:20 to the component 1). These ratios are also suitable for mixtures applied by seed treatment.

[1277] When mixtures comprising microbial pesticides are employed in crop protection, the application rates range from 1 x 106to 5 x 1016(or more) CFU / ha, preferably from 1 x 108to 1 x 1013CFU / ha, even more preferably from 1 x 109to 5 x 1015CFU / ha, and in particular from 1 x 1012to 5 x 1014CFU / ha. In the case of nematodes as microbial pesticides (e.g. S. feltiae), the application rates regularly range from 1 x 105to 1 x 1012(or more), preferably from 1 x 108to 1 x 1011, more preferably from 5 x 108to 1 x 1010individuals (e.g. in the form of eggs, juvenile or any other live stages, preferably in an infective juvenile stage) per ha.

[1278] When mixtures comprising microbial pesticides are employed in seed treatment, the application rates generally range from 1 x 106to 1 x 1012(or more) CFU / seed, preferably from 1 x 106to 1 x 109CFU / seed. Furthermore, the application rates per 100 kg of seed generally range from 1 x 107to 1 x 1014(or more) CFU, preferably from 1 x 109to 1 x 1012CFU.

[1279] Preference is given to mixtures comprising as component 2) at least one active substance selected from inhibitors of complex III at Qosite in group A), more preferably selected from compounds (A.1.1), (A.1.4), (A.1.8), (A.1.9), (A.1.10), (A.1.12), (A.1.13), (A.1.14), (A.1.17), (A.1.21), (A.1.22), (A1.24), (A.1.25), (A.1.34) and (A.1.35); particularly selected from (A.1.1), (A.1.4), (A.1.8), (A.1.9), (A.1.13), (A.1.14), (A.1.17), (A.1.21), (A.1.24), (A.1.25), (A.1.34) and (A.1.35).

[1280] Preference is also given to mixtures comprising as component 2) at least one active substance selected from inhibitors of complex III at Qi site in group A), more preferably selected from compounds (A.2.1), (A.2.3), (A.2.4) and (A.2.6); particularly selected from (A.2.3), (A.2.4) and (A.2.6).

[1281] Preference is also given to mixtures comprising as component 2) at least one active substance selected from inhibitors of complex II in group A), more preferably selected from compounds (A.3.2), (A.3.3), (A.3.4), (A.3.7), (A.3.9), (A.3.11), (A.3.12), (A.3.15), (A.3.16), (A.3.17), (A.3.18), (A.3.19), (A.3.20), (A.3.21), (A.3.22), (A.3.23), (A.3.24), (A.3.28), (A.3.31), (A.3.32), (A.3.33), (A.3.34), (A.3.35), (A.3.36), (A.3.37), (A.3.38) and (A.3.39); particularly selected from (A.3.2), (A.3.3), (A.3.4), (A.3.7), (A.3.9), (A.3.12), (A.3.15), (A.3.17), (A.3.19), (A.3.22), (A.3.23),250444W001

[1282] 117

[1283] (A.3.24), (A.3.31), (A.3.32), (A.3.33), (A.3.34), (A.3.35), (A.3.36), (A.3.37), (A.3.38) and (A.3.39).

[1284] Preference is also given to mixtures comprising as component 2) at least one active substance selected from other respiration inhibitors and QoSI in group A), more preferably selected from compounds (A.4.5) and (A.5.1); in particular (A.5.1).

[1285] Preference is also given to mixtures comprising as component 2) at least one active substance selected from C14 demethylase inhibitors in group B), more preferably selected from compounds (B.1.4), (B.1.5), (B.1.8), (B.1.10), (B.1.11), (B.1.12), (B.1.13), (B.1.17), (B.1.18), (B.1.21), (B.1.22), (B.1.23), (B.1.25), (B.1.26), (B.1.29), (B.1.33), (B.1.34), (B.1.37), (B.1.38), (B.1.43), (B.1.46), (B.1.53), (B.1.54), (B.1.55), (B.1.56) and (B.1.57); particularly selected from (B.1.5), (B.1.8), (B.1.10), (B.1.17), (B.1.22), (B.1.23), (B.1.25), (B.1.33), (B.1.34), (B.1.37), (B.1.38), (B.1.43) and (B.1.46), (B.1.56) and (B.1.57).

[1286] Preference is also given to mixtures comprising as component 2) at least one active substance selected from Delta14-reductase inhibitors in group B), more preferably selected from compounds (B.2.4), (B.2.5), (B.2.6) and (B.2.8); in particular (B.2.4). Preference is also given to mixtures comprising as component 2) at least one active substance selected from phenylamides and acyl amino acid fungicides in group C), more preferably selected from compounds (C.1.1), (C.1.2), (C.1.4) and (C.1.5); particularly selected from (C.1.1) and (C.1.4). Preference is also given to mixtures comprising as component 2) at least one active substance selected from other nucleic acid synthesis inhibitors in group C), more preferably selected from compounds (C.2.6), (C.2.7), (C.2.8), (C.5.1), (C.5.2) and (C.5.3); in particular from (C.5.1), (C.5.2) and (C.5.3).

[1287] Preference is also given to mixtures comprising as component 2) at least one active substance selected from group D), more preferably selected from compounds (D.1.1), (D.1.2), (D.1.5), (D.2.4) and (D.2.6); particularly selected from (D.1.2), (D.1.5) and (D.2.6).

[1288] Preference is also given to mixtures comprising as component 2) at least one active substance selected from group E), more preferably selected from compounds (E.1.1), (E.1.3), (E.2.2) and (E.2.3); in particular (E.1.3).

[1289] Preference is also given to mixtures comprising as component 2) at least one active substance selected from group F), more preferably selected from compounds (F.1.2), (F.1.4) and (F.1.5). Preference is also given to mixtures comprising as component 2) at least one active substance selected from group G), more preferably selected from compounds (G.5.1), (G.5.3), (G.5.4), (G.5.5), G.5.6), G.5.7), (G.5.8), (G.5.9), (G.5.10) and (G.5.11); particularly selected from (G.5.1) and (G.5.3).

[1290] Preference is also given to mixtures comprising as component 2) at least one active substance selected from group H), more preferably selected from compounds (H.2.2), (H.2.3), (H.2.5), (H.2.7), (H.2.8), (H.3.2), (H.3.4), (H.3.5), (H.4.9) and (H.4.10); particularly selected from (H.2.2), (H.2.5), (H.3.2), (H.4.9) and (H.4.10).

[1291] Preference is also given to mixtures comprising as component 2) at least one active substance selected from group I), more preferably selected from compounds (1.2.2), (1.2.5), (1.3.1), (1.3.3) and (1.3.6); in particular (1.3.1).250444W001

[1292] 118

[1293] Preference is also given to mixtures comprising as component 2) at least one active substance selected from group J), more preferably selected from compounds (J.1.2), (J.1.5), (J.1.8), (J.1.11) and (J.1.12); in particular (J.1.5).

[1294] Preference is also given to mixtures comprising as component 2) at least one active substance selected from group K), more preferably selected from compounds (K.1.24), (K.1.41), (K.1.42), (K.1.57), (K.1.58), (K.1.59) and (K.1.60); particularly selected from (K.1.24), (K.1.41), (K.1.57), (K.1.58), (K.1.59) and (K.1.60).

[1295] The biopesticides from group L1) and / or L2) may also have insecticidal, acaricidal, molluscicidal, pheromone, nematicidal, plant stress reducing, plant growth regulator, plant growth promoting and / or yield enhancing activity. The biopesticides from group L3) and / or L4) may also have fungicidal, bactericidal, viricidal, plant defense activator, plant stress reducing, plant growth regulator, plant growth promoting and / or yield enhancing activity. The biopesticides from group L5) may also have fungicidal, bactericidal, viricidal, plant defense activator, insecticidal, acaricidal, molluscicidal, pheromone and / or nematicidal activity.

[1296] The microbial pesticides, in particular those from groups L1), L3) and L5), embrace not only the isolated, pure cultures of the respective microorganism as defined herein, but also its cell-free extract, its suspension in a whole broth culture and a metabolite-containing culture medium or a purified metabolite obtained from a whole broth culture of the microorganism.

[1297] Many of these biopesticides have been deposited under deposition numbers mentioned herein (the prefixes such as ATCC or DSM refer to the acronym of the respective culture collection, for details see e.g. here: http: / / www. wfcc.info / ccinfo / collection / by acronym / ), are referred to in literature, registered and / or are commercially available: mixtures of Aureobasidium pullulans DSM 14940 and DSM 14941 isolated in 1989 in Konstanz, Germany (e.g. blastospores in BlossomProtect® from bio-ferm GmbH, Austria), Azospirillum brasilense Sp245 originally isolated in wheat reagion of South Brazil (Passo Fundo) at least prior to 1980 (BR 11005; e.g. GELFIX® Gram neas from BASF Agricultural Specialties Ltd., Brazil), A. brasilense strains Ab-V5 and Ab-V6 (e.g. in AzoMax from Novozymes BioAg Produtos papra Agricultura Ltda., Quattro Barras, Brazil or Simbiose-Malz® from Simbiose-Agro, Brazil; Plant Soil 331, 413-425, 2010), Bacillus amyloliquefaciens strain AP-188 (NRRL B-50615 and B-50331; US 8,445,255); B. amyloliquefaciens ssp. plantarum strains formerly B. subtilis, recently classified as B. velezensis (Int. J. Syst. Evol. Microbiol. 66, 1212-1217, 2016): B. a. ssp. plantarum or B. velezensis D747 isolated from air in Kikugawa-shi, Japan (US 20130236522 A1 ; FERM

[1298] BP-8234; e.g. Double Nickel™ 55 WDG from Certis LLC, USA), B. a. ssp. plantarum or B. velezensis FZB24 isolated from soil in Brandenburg, Germany (also called SB3615; DSM 96-2; J. Plant Dis. Prot. 105, 181-197, 1998; e.g. Taegro® from Novozyme Biologicals, Inc., USA), B. a. ssp. plantarum or B. velezensis FZB42 isolated from soil in Brandenburg, Germany (DSM 23117; J. Plant Dis. Prot. 105, 181-197, 1998; e.g. RhizoVital® 42 from AbiTEP GmbH, Germany), B. a. ssp. plantarum or B. velezensis MBI600 isolated from faba bean in Sutton Bonington, Nottinghamshire, U.K. at least before 1988 (also called 1430; NRRL B-50595; US 2012 / 0149571 A1 ; e.g. Integral® from BASF Corp., USA), B. a. ssp. plantarum or B. velezensis QST-713 isolated from peach orchard in 1995 in California, U.S.A. (NRRL B-21661; e.g. Serenade® MAX from Bayer Crop Science LP, USA), B. a. ssp. plantarum or B. velezensis TJ1000 isolated in 1992 in South Dakoda, U.S.A, (also called 1BE; ATCC BAA-390; CA250444W001

[1299] 119

[1300] 2471555 A1; e.g. QuickRoots™ from TJ Technologies, Watertown, SD, USA); B. firmus CNCM 1-1582, a variant of parental strain EIP-N1 (CNCM 1-1556) isolated from soil of central plain area of Israel (WO 2009 / 126473, US 6,406,690; e.g. Votivo® from Bayer CropScience LP, USA), B. pumilus GHA 180 isolated from apple tree rhizosphere in Mexico (IDAC 260707-01; e.g. PROMIX® BX from Premier Horticulture, Quebec, Canada), B. pumilus INR-7 otherwise referred to as BU-F22 and BU-F33 isolated at least before 1993 from cucumber infested by Erwinia tracheiphila (NRRL B-50185, NRRL B-50153; US 8,445,255), B. pumilus KFP9F isolated from the rhizosphere of grasses in South Africa at least before 2008 (NRRL B-50754;

[1301] WO 2014 / 029697; e.g. BAC-UP or FUSION-P from BASF Agricultural Specialities (Pty) Ltd., South Africa), B. pumilus QST 2808 was isolated from soil collected in Pohnpei, Federated States of Micronesia, in 1998 (NRRL B-30087; e.g. Sonata® or Ballad® Plus from Bayer Crop Science LP, USA), B. simplex ABU 288 (NRRL B-50304; US 8,445,255), B. subtilis FB17 also called UD 1022 or UD10-22 isolated from red beet roots in North America (ATCC PTA-11857; System. Appl. Microbiol. 27, 372-379, 2004; US 2010 / 0260735; WO 2011 / 109395); B. thurin-giensis ssp. aizawai ABTS-1857 isolated from soil taken from a lawn in Ephraim, Wisconsin, U.S.A., in 1987 (also called ABG-6346; ATCC SD-1372; e.g. XenTari® from BioFa AG, Munsingen, Germany), B. t. ssp. kurstaki ABTS-351 identical to HD-1 isolated in 1967 from diseased Pink Bollworm black larvae in Brownsville, Texas, U.S.A. (ATCC SD-1275; e.g. Dipel® DF from Valent BioSciences, IL, USA), B. t. ssp. kurstaki SB4 isolated from E. saccharina larval cadavers (NRRL B-50753; e.g. Beta Pro® from BASF Agricultural Specialities (Pty) Ltd., South Africa), B. t. ssp. tenebrionis NB-176-1, a mutant of strain NB-125, a wild type strain isolated in 1982 from a dead pupa of the beetle Tenebrio molitor (DSM 5480; EP 585215 B1; e.g.

[1302] Novodor® from Valent BioSciences, Switzerland), Beauveria bassiana GHA (ATCC 74250; e.g. BotaniGard® 22WGP from Laverlam Int. Corp., USA), B. bassiana JW-1 (ATCC 74040; e.g. Naturalis® from CBC (Europe) S.r.l. , Italy), B. bassiana PPRI 5339 isolated from the larva of the tortoise beetle Conchyloctenia punctata (NRRL 50757; e.g. BroadBand® from BASF Agricultural Specialities (Pty) Ltd., South Africa), Bradyrhizobium elkanii strains SEMIA 5019 (also called 29W) isolated in Rio de Janeiro, Brazil and SEMIA 587 isolated in 1967 in the State of Rio Grande do Sul, from an area previously inoculated with a North American isolate, and used in commercial inoculants since 1968 (Appl. Environ. Microbiol. 73(8), 2635, 2007; e.g. GELFIX 5 from BASF Agricultural Specialties Ltd., Brazil), B. japonicum 532c isolated from Wisconsin field in U.S.A. (Nitragin 61A152; Can. J. Plant. Sci. 70, 661-666, 1990; e.g. in Rhizoflo®, Histick®, Hicoat® Super from BASF Agricultural Specialties Ltd., Canada), B. japonicum E-109 variant of strain USDA 138 (INTA E109, SEMIA 5085; Eur. J. Soil Biol. 45, 28-35, 2009; Biol. Fertil. Soils 47, 81-89, 2011); B. japonicum strains deposited at SEMIA known from Appl. Environ. Microbiol. 73(8), 2635, 2007: SEMIA 5079 isolated from soil in Cerrados region, Brazil by Embrapa-Cerrados used in commercial inoculants since 1992 (CPAC 15; e.g. GELFIX 5 or ADHERE 60 from BASF Agricultural Specialties Ltd., Brazil), B. japonicum SEMIA 5080 obtained under lab condtions by Embrapa-Cerrados in Brazil and used in commercial inoculants since 1992, being a natural variant of SEMIA 586 (CB1809) originally isolated in U.S.A. (CPAC 7; e.g. GELFIX 5 or ADHERE 60 from BASF Agricultural Specialties Ltd., Brazil); Burkholderia sp. A396 isolated from soil in Nikko, Japan, in 2008 (NRRL B-50319; WO 2013 / 032693;

[1303] Marrone Bio Innovations, Inc., USA), Coniothyrium minitans CON / M / 91-08 isolated from oilseed rape (WO 1996 / 021358; DSM 9660; e.g. Contans® WG, Intercept® WG from Bayer Crop-Science AG, Germany), harpin (alpha-beta) protein (Science 257, 85-88, 1992; e.g.250444W001

[1304] 120

[1305] Messenger™ or HARP-N-Tek from Plant Health Care pic, U.K.), Helicoverpa armigera nucleopolyhedrovirus (HearNPV) (J. Invertebrate Pathol. 107, 112-126, 2011; e.g. Helicovex® from Adermatt Biocontrol, Switzerland; Diplomata® from Koppert, Brazil; Vivus® Max from AgBiTech Pty Ltd., Queensland, Australia), Helicoverpa zea single capsid nucleopolyhedrovirus (HzSNPV) (e.g. Gemstar® from Certis LLC, USA), Helicoverpa zea nucleopolyhedrovirus ABA-NPV-U (e.g. Heligen® from AgBiTech Pty Ltd., Queensland, Australia), Heterorhabditis bacteriophora (e.g. Nemasys® G from BASF Agricultural Specialities Limited, UK), Isaria fumosorosea Apopka-97 isolated from mealy bug on gynura in Apopka, Florida, U.S.A. (ATCC 20874; Biocontrol Science Technol. 22(7), 747-761 , 2012; e.g. PFR-97™ or PreFeRal® from Certis LLC, USA), Metarhizium anisopliae var. anisopliae F52 also called 275 or V275 isolated from codling moth in Austria (DSM 3884, ATCC 90448; e.g. Met52® Novozymes Biologicals BioAg Group, Canada), Metschnikowia fructicola 277 isolated from grapes in the central part of Israel (US 6,994,849; NRRL Y-30752; e.g. formerly Shemer® from Agrogreen, Israel), Paecilomyces ilacinus 251 isolated from infected nematode eggs in the Philippines (AGAL 89 / 030550; WQ1991 / 02051 ; Crop Protection 27, 352-361, 2008; e.g. BioAct®from Bayer Crop-Science AG, Germany and MeloCon® from Certis, USA), Paenibacillus alvei NAS6G6 isolated from the rhizosphere of grasses in South Africa at least before 2008 (WO 2014 / 029697; NRRL B-50755; e.g. BAC-UP from BASF Agricultural Specialities (Pty) Ltd., South Africa), Paenibacillus strains isolated from soil samples from a variety of European locations including Germany: P. epiphyticus Lu17015 (WO 2016 / 020371; DSM 26971), P. polymyxa ssp. plantarum Lu16774 (WO 2016 / 020371; DSM 26969), P. p. ssp. plantarum strain Lu17007 (WO 2016 / 020371; DSM 26970); Pasteuria nishizawae Pn1 isolated from a soybean field in the mid-2000s in Illinois, U.S.A. (ATCC SD-5833; Federal Register 76(22), 5808, February 2, 2011; e.g. Clariva™ PN from Syngenta Crop Protection, LLC, USA), Penicillium bilaiae (also called P. bilaif) strains ATCC 18309 (= ATCC 74319), ATCC 20851 and / or ATCC 22348 (= ATCC 74318) originally isolated from soil in Alberta, Canada (Fertilizer Res. 39, 97-103, 1994; Can. J. Plant Sci. 78(1), 91-102, 1998; US 5,026,417, WO 1995 / 017806; e.g. Jump Start®, Provide® from Novozymes Biologicals BioAg Group, Canada), Reynoutria sachalinensis extract (EP 0307510 B1 ; e.g. Regalia® SC from Marrone BioInnovations, Davis, CA, USA or Milsana® from BioFa AG, Germany), Steinernema carpocapsae (e.g. Millenium® from BASF Agricultural Specialities Limited, UK), S. feltiae (e.g. Nemashield® from BioWorks, Inc., USA; Nemasys® from BASF Agricultural Specialities Limited, UK), Streptomyces microflavus NRRL B-50550

[1306] (WO 2014 / 124369; Bayer CropScience, Germany), Trichoderma asperelloides JM41R isolated in South Africa (NRRL 50759; also referred to as T. fertile’ e.g. Trichoplus® from BASF Agricultural Specialities (Pty) Ltd., South Africa), T. harzianum T-22 also called KRL-AG2 (ATCC 20847; BioControl 57, 687-696, 2012; e.g. Plantshield® from BioWorks Inc., USA or SabrEx™ from Advanced Biological Marketing Inc., Van Wert, OH, USA).

[1307] According to another embodiment of the mixtures, the at least one pesticide II is selected from the groups L1) to L5):

[1308] L1) Microbial pesticides with fungicidal, bactericidal, viricidal and / or plant defense activator activity: Aureobasidium pullulans DSM 14940 and DSM 14941 (L1.1), Bacillus amyloliquefaciens AP-188 (L.1.2), B. amyloliquefaciens ssp. plantarum D747 (L.1.3), B. amyloliquefaciens ssp. plantarum FZB24 (L.1.4), B. amyloliquefaciens ssp. plantarum FZB42 (L.1.5), B. amyloliquefaciens ssp. plantarum MBI600 (L.1.6), B. amyloliquefaciens ssp. plantarum250444W001

[1309] 121

[1310] QST-713 (L.1.7), B. amyloliquefaciens ssp. plantarum TJ1000 (L.1.8), B. pumilus GB34 (L.1.9), B. pumilus GHA 180 (L.1.10), B. pumilus INR-7 (L.1.11), B. pumilus KFP9F (L.1.12), B. pumilus QST 2808 (L.1.13), B. simplex ABU 288 (L.1.14), B. subtilis FB17 (L.1.15), Coniothyrium minitans CON / M / 91-08 (L.1.16), Metschnikowia fructicola NRRL Y-30752 (L.1.17), Paenibacillus a / ve / NAS6G6 (L.1.18), P. epiphyticus Lu 17015 (L.1.25), P. polymyxa ssp. plantarum Lu16774 (L.1.26), P. p. ssp. plantarum strain Lu17007 (L.1.27), Penicillium bilaiae ATCC 22348 (L.1.19), P. bilaiae ATCC 20851 (L.1.20), Penicillium bilaiae ATCC 18309 (L.1.21), Streptomyces microflavus NRRL B-50550 (L.1.22), Trichoderma asperelloides JM41 R (L.1.23), T. harzianum T-22 (L.1.24);

[1311] L2) Biochemical pesticides with fungicidal, bactericidal, viricidal and / or plant defense activator activity: harpin protein (L.2.1), Reynoutria sachalinensis extract (L.2.2);

[1312] L3) Microbial pesticides with insecticidal, acaricidal, molluscidal and / or nematicidal activity:

[1313] Bacillus firmus 1-1582 (L.3.1); B. thuringiensis ssp. aizawai ABTS-1857 (L.3.2), B. t. ssp. kurstaki ABTS-351 (L.3.3), B. t. ssp. kurstaki SB4 (L.3.4), B. t. ssp. tenebrionis NB-176-1 (L.3.5), Beauveria bassiana GHA (L.3.6), B. bassiana JW-1 (L.3.7), B. bassiana PPRI 5339 (L.3.8), Burkholderia sp. A396 (L.3.9), Helicoverpa armigera nucleopolyhedrovirus (HearNPV) (L.3.10), Helicoverpa zea nucleopolyhedrovirus (HzNPV) ABA-NPV-U (L.3.11), Helicoverpa zea single capsid nucleopolyhedrovirus (HzSNPV) (L.3.12), Heterohabditis bacteriophora (L.3.13), Isaria fumosorosea Apopka-97 (L.3.14), Metarhizium anisopliae var. anisopliae F52 (L.3.15), Paecilomyces Hlacinus 251 (L.3.16), Pasteuria nishizawae Pn1 (L.3.17), Steinernema carpocapsae (L.3.18), S. feltiae (L.3.19);

[1314] L4) Biochemical pesticides with insecticidal, acaricidal, molluscidal, pheromone and / or nematicidal activity: cis-jasmone (L.4.1), methyl jasmonate (L.4.2), Quillay extract (L.4.3); L5) Microbial pesticides with plant stress reducing, plant growth regulator, plant growth promoting and / or yield enhancing activity: Azospirillum brasilense Ab-V5 and Ab-V6 (L.5.1), A. brasilense Sp245 (L.5.2), Bradyrhizobium elkanii SEMIA 587 (L.5.3), B. elkanii SEMIA 5019 (L.5.4), B. japonicum 532c (L.5.5), B. japonicum E-109 (L.5.6), B. japonicum SEMIA 5079 (L.5.7), B. japonicum SEMIA 5080 (L.5.8).

[1315] The present invention furthermore relates to agrochemical compositions comprising a mixture of at least one compound I (component 1) and at least one biopesticide selected from the group L) (component 2), in particular at least one biopesticide selected from the groups L1) and L2), as described above, and if desired at least one suitable auxiliary.

[1316] The present invention furthermore relates to agrochemical compositions comprising a mixture of at least one compound I (component 1) and at least one biopesticide selected from the group L) (component 2), in particular at least one biopesticide selected from the groups L3) and L4), as described above, and if desired at least one suitable auxiliary.

[1317] Preference is also given to mixtures comprising as pesticide II (component 2) a biopesticide selected from the groups L1), L3) and L5), preferably selected from strains denoted above as (L.1.2), (L.1.3), (L.1.4), (L.1.5), (L.1.6), (L.1.7), (L.1.8), (L.1.10), (L.1.11), (L.1.12), (L.1.13), (L.1.14), (L.1.15), (L.1.17), (L.1.18), (L.1.19), (L.1.20), (L.1.21), (L.1.25), (L.1.26), (L.1.27), (L.3.1); (L.3.9), (L.3.16), (L.3.17), (L.5.1), (L.5.2), (L.5.3), (L.5.4), (L.5.5), (L.5.6), (L.5.7), (L.5.8); (L.4.2), and (L.4.1); even more preferably selected from (L.1.2), (L.1.6), (L.1.7), (L.1.8), (L.1.11),250444W001

[1318] 122

[1319] (L.1.12), (L.1.13), (L.1.14), (L.1.15), (L.1.18), (L.1.19), (L.1.20), (L.1.21), (L.3.1); (L.3.9), (L.3.16), (L.3.17), (L.5.1), (L.5.2), (L.5.5), (L.5.6); (L.4.2), and (L.4.1). These mixtures are particularly suitable for treatment of propagation materials, i. e. seed treatment purposes and likewise for soil treatment. These seed treatment mixtures are particularly suitable for crops such as cereals, corn and leguminous plants such as soybean.

[1320] Preference is also given to mixtures comprising as pesticide II (component 2) a biopesticide selected from the groups L1), L3) and L5), preferably selected from strains denoted above as (L1.1), (L.1.2), (L.1.3), (L.1.6), (L.1.7), (L.1.9), (L.1.11), (L.1.12), (L.1.13), (L.1.14), (L.1.15), (L.1.17), (L.1.18), (L.1.22), (L.1.23), (L.1.24), (L.1.25), (L.1.26), (L.1.27), (L.2.1), (L.2.2), (L.2.3), (L.2.4), (L.2.5), (L.2.6), (L.2.7), L.2.8), (L.2.9), (L.2.10), (L.3.2), (L.3.3), (L.3.4), (L.3.5), (L.3.6), (L.3.7), (L.3.8), (L.3.10), (L.3.11), (L.3.12), (L.3.13), (L.3.14), (L.3.15), (L.3.18), (L.3.19); (L.4.2), even more preferably selected from (L.1.2), (L.1.7), (L.1.11), (L.1.13), (L.1.14), (L.1.15), (L.1.18), (L.1.23), (L.2.5), (L.2.6), (L.3.3), (L.3.4), (L.3.6), (L.3.7), (L.3.8), (L.3.10), (L.3.11), (L.3.12), (L.3.15), and (L.4.2). These mixtures are particularly suitable for foliar treatment of cultivated plants, preferably of vegetables, fruits, vines, cereals, corn, and leguminous crops such as soybeans.

[1321] The compositions comprising mixtures of active ingredients can be prepared by usual means, e.g. by the means given for the compositions of compounds I. When living microorganisms, such as pesticides II from groups L1), L3) and L5), form part of the compositions, such compositions can be prepared by usual means (e.g., H.D. Burges: Formulation of Microbial Biopesticides, Springer, 1998; WO 2008 / 002371, US 6,955,912, US 5,422,107).

[1322] I. Synthesis examples

[1323] Example 1 : (5-(6,7-dimethvlpyrazolo[ 1 ,5-a1pvridine-3-vl')-3.3-dimethvl-2.3-dihvdro-benzo[f][1 ,4]oxazepine)

[1324] Step 1: (2,2-dimethyl-2,3-dihydro-4H-benzo[e][1,3]oxazin-4-one)

[1325] p-TsOH (694 mg, 0.05 eq) was added to a suspension of 2-hydroxy-benzamide (10 g, 1 eq) and 2,2-dimethoxypropane (15.2 g, 2 eq) in toluene (150 mL), and the mixture was heated at reflux with azeotropic removal of water for 3 hours. The reaction was cooled and concentrated in vacuo, and the resultant residue was diluted with ethyl acetate, washed successively with 2 N hydrogen chloride, water and brine, and dried over anhydrous magnesium sulfate. Removal of solvent in vacuo afforded the titled compound, which was used in the next step without further purification.

[1326] Step 2: (2,2-dimethyl-2H-benzo[e][1 ,3]oxazine-4-yl trifluoromethanesulfonate)

[1327] Trifluoromethanesulfonic anhydride (3.18 g, 1 eq) and 2,6-lutidine (1.21 g, 1 eq) were added dropwise to a suspension of 2,2-dimethyl-2,3-dihydro-4H-benzo[e][1,3]oxazin-4-one (2.0 g, 1250444W001

[1328] 123

[1329] eq) in dichloromethane (5.0 mL) under cooling at -78 °C, and the mixture was stirred at the same temperature for 1 hour. The reaction mixture stirred for 20 minutes at 0 °C, poured into ice water, and the solution was extracted with dichloromethane. The organic layer was washed successively with a saturated aqueous solution of sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to give the titled compound (1.74 g) as a brown oil.

[1330] Step 3: (5-(6,7-dimethylpyrazolo[1 ,5-a]pyridine-3-yl)-3,3-dimethyl-2,3-dihydrobenzo[ / ][1 ,4]oxaze-pine)

[1331] (5-methoxy-3-pyridyl)boronic acid (136 mg, 1.1 eq), potassium carbonate (447 mg, 4.0 eq), water (1.0 mL) and bis(triphenylphosphine)palladium(ll)dichloride (113 mg, 0.2 eq) were added to a solution of 2,2-dimethyl-2H-benzo[e][1,3]oxazine-4-yl trifluoromethanesulfonate (625 mg, 1 eq) in dimethoxyethane (5 mL), and the mixture was stirred under argon atmosphere at 80 °C for 12 hours. After cooling, the reaction mixture was filtered, and the filtrate was diluted with ethyl acetate. The solution was washed successively with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The crude product was purified by High Performance Liquid Chromatography on silica gel (HPLC-column KinetexXB C18 1 ,7p (50 x 2,1 mm); eluent: acetonitrile / water (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) to give the titled compound (40 mg) as a yellow-brown oil.

[1332] 1H NMR (400 MHz, CDCI3) p [ppm]: 8.39 (dd, J = 5.1 , 2.3 Hz, 2H), 7.41 - 7.34 (m, 2H), 7.15 (dd, J= 8.1, 1.6 Hz, 1H), 6.93 -6.87 (m, 2H), 3.89 (s, 3H), 1.65 (s, 6H).

[1333] Table I: Compounds Ex-1 to Ex-54 of formula I, wherein the meaning of Z, R1, R2, R3, R4, R5, R6, R7, R8, R9, X1, X2and w are as defined in each line.

[1334]

[1335] x-No Z w R1R2R3R4R5R6R7R8R9X1X2LS_MS_MZ HPLC Rt

[1336] x-1 Rac 0 0 H F H OCH3- - - F H 317.2 1.264

[1337] CH2CH2CH2- x-2 Rac 0 0 H F H OCH3CH3CH3- - - Cl H 321.2 1.278

[1338] CH2-4- x-3 Rac 0 0 H H Cl H CH3- - - H H 367.2 1.402

[1339] F-Ph

[1340] x-4 Rac 0 0 H H Cl H CH34-CI-Ph - - - H H 369.1 1.449 x-5 Rac 0 0 H H Cl H CH34-F-Ph - - - H H 352.9 1.368 x-6 Rac 0 0 H OCH3H H - - - Cl H 315.1 1.032

[1341] CH2CH2CH2- x-7 Rac 0 0 H F H OCH3- - - H Cl 333.1 1.395

[1342] CH2CH2CH2- x-8 - - - Rac 0 0 H OCH3H H CH3CH3H H 269.2 0.91 x-9 Rac 0 0 H OCH3H H CH3CH3- - - F H 286.9 0.925 x- 10 Rac 0 0 H OCH3H H CH3CH3- - - Cl H 302.8 1.024 x- 11 Rac s 1 H Br H CN CH3H H H - F H 377.8 1.261 x- 12 Rac s 1 H CH=CH2H Br H H H H - F H 393* 1.505 x- 13 Rac s 1 H SCH3H CN CH3CH3CH3CH3- F H 358.1* 3.277 x- 14 Rac s 1 H CH3H Br H H CH3CH3- F H 365* 1.997

[1343]

[1344] Rac S 1 H CH3H Br H H CH3CH3- F H 378.9* 1.709 Rac S 1 H Br H CN CH3CH3CH3CH3- F H 391.9* 1.624 (S.S) s 1 H H Cl H CH3H H H - F H 321.1* 1.426* (S.S) s 1 H Br H H CH3H H H - F H 365* 0.995** (S.S) s 1 H Cl H H CH3H H H - F H 321.2* 2.309***

[1345] 0- Rac N 0 CH3H CH3H CH3CH3- - CH3H 399.2* 1.288

[1346] Ph

[1347] (S.S) S 1 H H Br H CH3H H H - F H 364.9* 2 170**** (S.S) S 1 H H CH3H CH3H CH3CH3- H F 301* 1.809***** (S) S 1 H H Cl H CH3H H H - H H 288.9* 1.543* (S.S) 0 1 H Cl H H CH3H CH3CH3- F H 305** 9.583 Rac S 0 H H CH3H CH3CH3- - - SCH3SCH3361* 1.134 Rac S 0 H H CH3H CH3CH3- - - F SCH3332.9* 1.127

[1348] H

[1349] Rac S 0 H CH3H CH3CH3- - - F OCH3317* 1.015 Rac s 0 H H CH3H CH3CH3- - - F F 304.9* 1.062 (S) 0 1 H H Cl H CH3H CH3CH3- F H 291*** 7.179

[1350]

[1351] (S) 0 1 H H CHF2H CH3H CH3CH3- F H 307*** 6.418 (S) S 1 H H Cl H CH3H H H - F H 308.9*** 8.408 (S) S 1 H H CHF2H CH3H H H - F H 323*** 7.473 (S) S 1 H Cl H H CH3H H H - F H 307*** 8.169 (S) 0 1 H H Br H CH3H H H - F H 334.9** 7.694 (S) 0 1 H Br H H CH3H H H - H F 334.9 7.264

[1352] H H

[1353] (S) 0 1 Cl H H CH3H H - H F 291 6.896 s H H

[1354] (S) 1 Br H H CH3H H - H F 350.9 8.522

[1355] H H

[1356] (S) 0 1 Br H H CH3H H - F H 335 7.431

[1357] H H H CHs H c

[1358] (S.S) 0 1 CN H - F H 296 8.65

[1359] H3

[1360] c

[1361] (S.S) 0 1 H H CHF2H CHs H H - H F 321 9.56

[1362] H3

[1363] (S) 0 1 H H CN H CHs H H H - H F 282 7.31 (S) 0 1 H H CHF2H CHs H H H - H F 307 7.31 (S) 0 1 H H Cl H CHs H H H - H F 291 6.576 Rac s 0 H H CHs H CHs C6H5- - - F H 349 1.196

[1364]

[1365] Rac S 0 H H CHs H CHs C6H5- - - H F 349.1 1.207 Rac S 0 H H CHs H CHs C6H5- - - F F 367.1 1.254 (S) N 1 H Cl H H CHs H H H H F H 290 2.442 (S) N 1 H Br H H CHs H H H H F H 335.9 2.522 (S) N 1 H Cl H H CHs H H H CHs F H 304 6.697 (S) N 1 H Br H H CHs H H H CHs F H 350 7.088 (S) S021 H H CHF2H CHs H H H - F H 355 5.426 (S) SO 1 H H CHF2H CHs H H H - F H 339 4.737 (S) N 1 H H CHF2H CHs H H H H F H 306 2.357 (S) N 1 H H CHF2H CHs H H H CHs F H 320 5.558

[1366]

[1367] 250444W001

[1368] 128

[1369] LC_MS methods:

[1370] If not marked standard method:

[1371] LCMS: Liquid chromatography-mass spectrometry; Shimadzu Nexera LC-30 LCMS-2020 (ESI+) using HPLC-column KinetexXB C18 1,7pm (50x2,1 mm); eluent: acetonitrile / water + 0.1% trifluoroacetic acid 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);

[1372] For marked following methods were used:

[1373] *LCMS-AC - LCMS: Liquid chromatography-mass spectrometry; Shimadzu Nexera LCMS DE-LIVER-220 (ESI+) using HPLC-column Luna-C183 pm (39 x 2.0 mm); eluent: acetonitrile+0.02 %(v / v) TFA / water+0.04 %(v / v) TFA (gradient from 5:95 to 100:0 in 3 min at 40°C, flow fate 0.8 mL / min);

[1374] ** i-Amylose-3 - LCMS: Liquid chromatography-mass spectrometry; Shimadzu Nexera LC-30 LCMS-2020 (ESI+) using HPLC-column LUX i-Amylose-35 pm (150 x 4.6 mm); eluent: acetonitrile I water + 0.1% formic acid (gradient from 50:50 to 100:0 in 10 min at 40°C, flow fate 0.6 mL / min);

[1375] *** Cellulose-1

[1376] LCMS: Liquid chromatography-mass spectrometry; Shimadzu Nexera LC-30 LCMS-2020 (ESI+) using HPLC-column LUX Cellulose-1 5 pm (150 x 4.6 mm); eluent: acetonitrile I water + 0.1% formic acid (gradient from 50:50 to 100:0 in 10 min at 40°C, flow fate 0.6 mL / min);

[1377] HPLC methods:

[1378] HPLC: High Performance Liquid Chromatography; HPLC-column KinetexXB C18 1 ,7p (50 x2,1 mm); eluent: acetonitrile / water + 0.1% trifluoroacetic acid (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).

[1379] Rt: retention time in minutes.

[1380] * SFC-(S,S)-WHELK-O1, 100*4.6mm I.D., 3.5um - SFC: Supercritical fluid chromatography; Waters UPCC with PDA using SFC-column : (S,S)-WHELK-O1 ,100x4.6mm I.D., 3.5um; eluent CO2 I MeOH (0.2%NH3(7M in MeOH), v / v) (gradient from 90:10 to 50:50 in 4 min at 35°C, 2000 psi, flow fate 3.4 mL / min);

[1381] ** SFC-Chiralpak IH-3, 100x4.6mm I.D.,3um - SFC: Supercritical fluid chromatography; Waters UPCC with PDA using SFC-column : Chiralpak IH-3, 100x4.6mm I.D.,3um; eluent CO2 I MeOH [0.2%NH3(7M in MeOH), v / v] (gradient from 90:10 to 50:50 in 4 min at 35°C, 2000 psi, flow fate 3.4 mL / min);

[1382] *** SFC-Chiralpak AD-3, 150x4.6mm I.D.,3um - SFC: Supercritical fluid chromatography; Waters UPCC with PDA using SFC-column : Chiralpak AD-3, 150x4.6mm I.D.,3um; eluent CO2 I IPA [0.2%NH3(7M in MeOH), v / v] (gradient from 90:10 to 50:50 in 4.5 min at 35°C, 2000 psi, flow fate 2.5 mL / min);

[1383] ”* SFC-Chiralpak IM-3, 100x4.6mm I.D.,3um - SFC: Supercritical fluid chromatography; Waters UPCC with PDA using SFC-column : Chiralpak IM-3, 100x4.6mm I.D.,3um; eluent CO2 / 250444W001

[1384] 129

[1385] MeOH [0.2%NH3(7M in MeOH), v / v] (gradient from 90:10 to 50:50 in 4.5 min at 35°C, 2000 psi, flow fate 3.4 mL / min);

[1386] **” SFC-Chiralcel OD-3, 150*4.6mm I.D.,3um - SFC: Supercritical fluid chromatography; Waters UPCC with PDA using SFC-column : Chiralcel OD-3, 150*4.6mm I.D.,3um; eluent CO2 I IPA [0.2%NH3(7M in MeOH), v / v] (gradient from 90:10 to 50:50 in 4.5 min at 35°C, 2000 psi, flow fate 2.5 mL / min).

[1387] Microtest

[1388] The active compounds were formulated separately as a stock solution having a concentration of 10000 ppm in dimethyl sulfoxide.

[1389] Example 1 - Activity against the grey mold Botrytis cinerea in the microtiterplate test The stock solutions were mixed according to the ratio, pipetted onto a micro titer plate (MTP) and diluted with water to the stated concentrations. A spore suspension of Botrci cinerea in an aqueous biomalt oryeast-bactopeptone-sodiumacetate solution was then added. The plates were placed in a water vapor-saturated chamber at a temperature of 18°C. Using an absorption photometer, the MTPs were measured at 405 nm 7 days after the inoculation.

[1390] In this test, the samples which had been treated with 31 ppm of the active substance from examples Ex-1, Ex-6, Ex-7, Ex-8, Ex-10, Ex-15, Ex-20, Ex-21, Ex-25, Ex-26, Ex-27, Ex-28 and Ex-31 respectively, showed 9 % growth of the pathogen.

[1391] Example 2 - Activity against Fusarium culmorum in the microtiterplate test

[1392] The stock solutions were mixed according to the ratio, pipetted onto a micro titer plate (MTP) and diluted with water to the stated concentrations. A spore suspension of Fusarium culmorum in an aqueous biomalt oryeast-bactopeptone-glycerine or DOB solution was then added. The plates were placed in a water vapor-saturated chamber at a temperature of 18°C. Using an absorption photometer, the MTPs were measured at 405 nm 7 days after the inoculation.

[1393] In this test, the samples which had been treated with 31 ppm of the active substance from examples Ex-6 and Ex-8 respectively, showed up to 16 % growth of the pathogen.

[1394] Example 3 - Activity against the leaf blotch on wheat caused by Sclerotinia sclerotiorum in the microtiterplate test

[1395] The active compounds were formulated separately as a stock solution having a concentration of 10000 ppm in dimethyl sulfoxide. The stock solutions were mixed according to the ratio, pipetted onto a micro titer plate (MTP) and diluted with water to the stated concentrations. A spore suspension of Sclerotinia sclerotiorum in an aqueous biomalt or yeast-bactopeptone-glycerine or DOB solution was then added.

[1396] In this test, the samples which had been treated with 31 ppm of the active substance from examples Ex-5, Ex-10, Ex-21, Ex-22, Ex-23, Ex-36 and Ex-43 respectively showed up to 19 % growth of the pathogen.

[1397] In this test, the samples which had been treated with 0.4 ppm of the active substance from examples Ex-17, Ex-18, Ex-31, Ex-32, Ex-33, Ex-34, Ex-35, Ex-36, Ex-38, Ex-40, Ex-42, Ex-44, Ex-49, Ex-50, Ex-53 and Ex-54 respectively showed up to 19 % growth of the pathogen.250444W001

[1398] 130

[1399] Example 4 - Activity against Corynespora cassiicola in the microtiterplate test

[1400] The stock solutions were mixed according to the ratio, pipetted onto a micro titer plate (MTP) and diluted with water to the stated concentrations. A spore suspension of the Corynespora cassiicola isolates in a DOB media (pH 7) was then added.

[1401] In this test, the samples which had been treated with 31 ppm of the active substance from examples Ex-44, Ex-45 and Ex-46 respectively, showed up to 3 % growth of the pathogen.

[1402] Example 5 - Activity against Cercospoea zea maydis in the microtiterplate test

[1403] The active compounds were formulated separately as a stock solution having a concentration of 10000 ppm in dimethyl sulfoxide. The stock solutions were mixed according to the ratio, pipetted onto a micro titer plate (MTP) and diluted with water to the stated concentrations. A spore suspension of Cercospoea zea maydis in an aqueous biomalt yeast-bactopeptone-glycerine or DOB solution was then added.

[1404] In this test, the samples which had been treated with 31 ppm of the active substance from examples Ex-44, Ex-45 and Ex-46 respectively, showed up to 7 % growth of the pathogen.

[1405] Example 6 - Activity against Pyricularia oryzae in the microtiterplate test

[1406] The active compounds were formulated separately as a stock solution having a concentration of 10000 ppm in dimethyl sulfoxide. The stock solutions were mixed according to the ratio, pipetted onto a micro titer plate (MTP) and diluted with water to the stated concentrations. A spore suspension of Pyricularia oryzae in an aqueous biomalt yeast-bactopeptone-glycerine or DOB solution was then added.

[1407] In this test, the samples which had been treated with 31 ppm of the active substance from examples Ex-39, Ex-40, Ex-44, Ex-45 and Ex-46 respectively, showed 0 % growth of the pathogen.

[1408] Green House

[1409] The compound was dissolved in a mixture of acetone and / or dimethylsulfoxide and the wetting agent / emulsifier Wettol, which is based on ethoxylated alkylphenoles, in a ratio (volume) solventemulsifier of 99 to 1 to give a total volume of 5 ml. Subsequently, water was added to total volume of 100 ml.

[1410] This stock solution was then diluted with the described solvent-emulsifier-water mixture to the final concentration given in the table below.

[1411] Example 1 - 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 previously described spray solution, containing the concentration of active ingredient or mixture mentioned in the table below. The next day the plants were inoculated with an aqueous biomalt or DOB solution containing the spore suspension of Botrytis cinerea. Then the plants were immediately transferred to a humid chamber. After 5 days at 22 to 24°C and a saturated relative humidity, the extent of fungal attack on the leaves was visually assessed as % diseased leaf area.250444W001

[1412] 131

[1413] In this test, the samples which had been treated with 125 ppm of the active substance from examples from examples Ex-31 , Ex-32, Ex-40, Ex-44, Ex-45, Ex-46, Ex-49 and Ex-54 respectively, showed up to 7 % growth of the pathogen whereas the untreated plants were 90% infected.

[1414] Example 2 - Preventative fungicidal control of white mold on soybean caused by Sclerotinia sclerotiorum

[1415] Young seedlings of soybeans were grown in pots. These plants were sprayed to run-off with previously described spray solution, containing the concentration of active ingredient or mixture mentioned in the table below. The next day the treated plants were inoculated with a suspension, containing the mycelium of Sclerotinia sclerotiorum. Then the trial plants were cultivated for 6 days in a greenhouse chamber at 23°C and a relative humidity between 80 and 85%. The extent of fungal attack on the leaves was visually assessed as % diseased leaf area.

[1416] In this test, the samples which had been treated with 125 ppm of the active substance from examples from examples Ex-33, Ex-34, Ex-40, Ex-44 and Ex-54 respectively, showed up to 20 % growth of the pathogen whereas the untreated plants were 90% infected.

Claims

250444W001132Claims1. A compound of formula I(I)whereinZ is NR9, O, S, SO or SO2;w is O or l;R1is in each case independently selected from H, halogen, CN, Ci-C6-alkyl, Ci-C6- halogenalkyl, O-Ci-C6-alkyl, S-Ci-C6-alkyl, 0-Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6- alkynyl, C3-C6-cycloalkyl;R2is in each case independently selected from H, halogen, CN, Ci-C6-alkyl, Ci-C6- halogenalkyl, O-Ci-C6-alkyl, S-Ci-C6-alkyl, 0-Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6- alkynyl, C3-C6-cycloalkyl;R3is in each case independently selected from H, halogen, CN, Ci-C6-alkyl, Ci-C6- halogenalkyl, O-Ci-C6-alkyl, S-Ci-C6-alkyl, 0-Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6- alkynyl, C3-C6-cycloalkyl;R4is in each case independently selected from H, halogen, CN, Ci-C6-alkyl, Ci-C6- halogenalkyl, O-Ci-C6-alkyl, S-Ci-C6-alkyl, 0-Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6- alkynyl, C3-C6-cycloalky;R5is in each case independently selected from hydrogen, halogen, CN, Ci-C6-alkyl, Ci-C6- halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, phenyl, benzyl, heterocyclic aromatics and CH2-heterocyclic aromatics where the mentioned aliphatic or aromatic radicals are unsubstituted or carry 1 , 2 or 3 substituents R5a;where each R5ais independently halogen, CN, Ci-C6-alkyl, Ci-C6-halogenalkyl or Ci-C6- alkoxy;R6is in each case independently selected from hydrogen, halogen, CN, Ci-C6-alkyl, Ci-C6- halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, phenyl, benzyl, heterocyclic aromatics and CH2-heterocyclic aromatics where the mentioned aliphatic or aromatic radicals are unsubstituted or carry 1, 2 or 3 substituents R6a;250444W001133where each R6ais independently halogen, CN, Ci-C6-alkyl, Ci-C6-halogenalkyl or Ci-C6- alkoxy; orR5and R6, together with the C atom to which they are bound, form an oxo group (=0); or a thioxo group (=S); orR5and R6, together with the carbon atom to which they are bound, form a 3-, 4-, 5- or 6-membered saturated carbocyclic ring or a 3-, 4-, 5- or 6-membered saturated heterocyclic ring containing 1 , 2 or 3 heteroatoms selected from O and S as ring members; where the carbocyclic or heterocyclic ring is unsubstituted or carries 1 , 2 or 3 substituents R56;where each R56is independently halogen, Ci-C6-alkyl or Ci-C6-halogenalkyl;R7is in each case independently selected from hydrogen, halogen, CN, Ci-C6-alkyl, Ci-C6- halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, phenyl, benzyl, heterocyclic aromatics and CH2-heterocyclic aromatics where the mentioned aliphatic or aromatic radicals are unsubstituted or carry 1 , 2 or 3 substituents R7a;where each R7ais independently halogen, CN, Ci-C6-alkyl, Ci-C6-halogenalkyl or Ci-C6- alkoxy;R8is in each case independently selected from hydrogen, halogen, CN, Ci-C6-alkyl, Ci-C6- halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, phenyl, benzyl, heterocyclic aromatics and CH2-heterocyclic aromatics where the mentioned aliphatic or aromatic radicals are unsubstituted or carry 1 , 2 or 3 substituents R8a;where each R8ais independently halogen, CN, Ci-C6-alkyl, Ci-C6-halogenalkyl or Ci-C6- alkoxy; orR7and R8, together with the carbon atom to which they are bound, form an oxo group (=0); or a thioxo group (=S); or a 3-, 4-, 5- or 6-membered saturated carbocyclic ring or a 3-, 4-, 5- or 6-membered saturated heterocyclic ring containing 1 , 2 or 3 heteroatoms selected from O and S as ring members; where the carbocyclic or heterocyclic ring is unsubstituted or carries 1 , 2 or 3 substituents R7 8,where each R78is independently halogen, Ci-C6-alkyl or Ci-C6-halogenalkyl;R9is in each case independently selected from H, CN, CH2CN, CH(CH3)CN, CH(=O), - C(=O)Ci-C6-alkyl, -C(=O)C2-C6-alkenyl, -C(=O)C2-C6-alkynyl, -C(=0)C3-C6-cycloalkyl, - C(=O)-N(H)Ci-C4-alkyl, -C(=O)-N(Ci-C4-alkyl)2, Ci-C6-alkyl, Ci-C6-alkoxy, Ci-C4- halogenalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, -S(=O)2-R9a, five- or six-membered heteroaryl, aryl or benzyl; wherein heteroaryl contains 1 , 2 or 3 heteroatoms selected from N, O and S as ring members; wherein aryl and the phenyl ring in benzyl are unsubstituted or carry 1 , 2, 3, 4 or 5 substituents selected from the group consisting of CN, halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy; wherein the phenyl ring in benzyl is unsubstituted or carries 1 , 2 or 3 substituents selected from the group consisting of CN and halogen;250444W001134whereinR9ais Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6- alkynyl, C2-C6-halogenalkynyl, phenyl or benzyl, where the phenyl ring in the two last-mentioned radicals is unsubstituted or carries 1 , 2 or 3 substituents each independently selected from the group consisting of halogen, Ci-C6-alkyl, Ci-C6- halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl and C2-C6- halogenalkynyl;X1is in each case independently selected from H, halogen, CN, Ci-C6-alkyl, Ci-C6- halogenalkyl, O-Ci-C6-alkyl, S-Ci-C6-alkyl, 0-Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6- alkynyl, C3-C6-cycloalkyl, phenyl, benzyl, O-phenyl, O-benzyl;X2is in each case independently selected from H, halogen, CN, Ci-C6-alkyl, Ci-C6- halogenalkyl, O-Ci-C6-alkyl, S-Ci-C6-alkyl, 0-Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6- alkynyl, C3-C6-cycloalkyl, phenyl, benzyl, O-phenyl, O-benzyl;whereinR2or R3, but not both, is H; andwith the proviso that if w is 0 and Z is O or S, R1is not Cl and CH3.and the N-oxides and the agriculturally acceptable salts thereof as fungicides.

2. The compound of claim 1 , wherein Z is S or O if w is 1.

3. The compound of any one of claims 1 to 2, Z is S, O or NR9if w is 0.

4. The compound of any one of claims 1 to 3, wherein R1and R4is H.

5. The compound of any one of claims 1 to 4, wherein R2and R3are independently selected from H, CN, halogen, Ci-C6-alkyl, Ci-C6-halogenalkyl, O-Ci-C6-alkyl, C2-C6- alkenyl, C3-C6-cycloalkyl.

6. The compound of any one of claims 1 to 5, wherein R2and R3are independently selected from H, CN, Cl, Br, CH3, C2H5, CHF2, CH2CH=CH2, cyclopropyl.

7. The compound of any one of claims 1 to 6, wherein R5and R6are independently selected from H, Ci-C6-alkyl, benzyl or they, together with the carbon atom to which they are bound, form C3-C6-cycloalkyl.250444W0011358. The compound of any one of claims 1 to 7, wherein R5and R6are independently selected from H, CH3, C2H5, benzyl or they, together with the carbon atom to which they are bound, form cyclopropyl.

9. The compound of any one of claims 1 to 8, wherein R7and R8are independently selected from H, Ci-C6-alkyl, benzyl or they, together with the carbon atom to which they are bound, form C3-C6-cycloalkyl.

10. The compound of any one of claims 1 to 9, wherein R7and R8are independently selected from H, CH3, C2H5, benzyl or they, together with the carbon atom to which they are bound, form cyclopropyl.

11. The compound of any one of claims 1 to 10, wherein R9is CN, Ci-C6-alkyl, C2-C6-alkenyl or C2-C6-alkynyl.

12. The compound of any one of claims 1 to 11 , wherein X1or X2are in each case independently selected from H, halogen, Ci-C6-alkyl, 0-Ci-C6-halogenalkyl or S-Ci-C6- alkyl.

13. The compound of any one of claims 1 to 12, wherein X1or X2are in each case independently selected from H, Cl, F, CH3, O-CH3or S-CH3.

14. A composition, comprising one compound of formula I, as defined in any of the claims 1 to 13, an N-oxide or an agriculturally acceptable salt thereof.

15. A method for combating phytopathogenic fungi, comprising 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, as defined in any of the claims 1 to 13 or with a composition, as defined in any of the claim 14.

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