Microbiocidal quinoline-amide compounds

Abstract

A compound of formula (I), wherein the substituents are as defined in the claims, and the agrochemically acceptable salts, or N-oxides of those compounds, which can be used as fungicides.

Description

[0001] MICROBIOCIDAL QUINOLINE-AMIDE COMPOUNDS

[0002] The present invention relates to microbiocidal quinoline-amide compounds, e.g., as active ingredients, which have microbiocidal activity, in particular fungicidal activity. The invention also relates to preparation of these quinoline-amide compounds, to intermediates useful in the preparation of these quinoline-amide compounds, to the preparation of these intermediates, to agrochemical compositions which comprise at least one of the quinoline-amide compounds, to preparation of these compositions and to the use of the quinoline-amide compounds or compositions in agriculture or horticulture for controlling or preventing infestation of plants, harvested food crops, seeds or non-living materials by phytopathogenic microorganisms, in particular fungi.

[0003] According to a first aspect of the present invention, there is provided a compound of formula (I):

[0004] R1is selected from hydrogen, halogen, cyano, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkyl, Cs-Ce-cycloalkyl, Ci- C4-alkylsulfanyl, Ci-C4-alkylsulfinyl, or Ci-C4-alkylsulfonyl;

[0005] R2is selected from hydrogen, halogen, cyano, or Ci-C4-alkyl;

[0006] B1is selected from CR4, or N;

[0007] B2is selected from CR5, or N;

[0008] R3, R4and R5are independently selected from hydrogen, halogen, cyano, hydroxy, amino, carboxy, C1-C4- alkyl, Ci-C4-haloalkyl, Ci-C4-haloalkoxy, Ci-C4-alkoxy, Cs-Cs-alkenyloxy, Cs-Ce-alkynyloxy, Ci-C4-alkylsulfanyl, Ci-C4-alkylsulfinyl, Ci-C4-alkylsulfonyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy, C1-C4- alkoxycarbonyl, Ci-C4-alkylcarbonyl, carbamoyl, Ci-C4-alkylaminocarbonyl, di(Ci-C6-alkyl)aminocarbonyl, cyano-Ci-C4-alkyl, N-Ci-C4-alkoxy-C-Ci-C4-alkyl-carbonimidoyl, N-hydroxy-C-Ci-C4-alkyl-carbonimidoyl, C1- C4-alkylamino, Ci-C4-dialkylamino, Ci-C4-alkylaminocarbonyl, Ci-C4-dialkylaminocarbonyl, trifluoromethylsulfonyloxy, phenyl, a 5- to 6-membered saturated, partially saturated or aromatic heteroaryl, or Cs-Ce-cycloalkyl; wherein any of said heteroaryl contains 1 , 2 or 3 heteroatoms independently selected from O, S, or N, with the proviso that only one is selected from O or S; wherein any of said phenyl and 5- to 6- membered saturated, partially saturated or aromatic heteroaryl are unsubstituted or substituted with 1 , 2, or 3 substituents independently selected from halogen, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, or Ci-C4-alkoxy; and wherein any of said Cs-Ce-cycloalkyl is unsubstituted or substituted with 1 , 2 or 3 substituents independently selected from halogen, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, or Ci-C4-alkoxy;

[0009] Q is a 5-membered aromatic heteroaryl, wherein said 5-membered aromatic heteroaryl is selected from pyrrol- 1-yl, pyrrol-2-yl, pyrrol-3-yl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-5-yl, imidazole-1-yl, Imidazole2-yl, imidazole-4- yl, triazol-1 -yl, triazol-2-yl, triazol-4-yl, 1 ,2,4-triazol-1 -yl, 1 ,2,4-triazol-3-yl, or tetrazol-5-yl; wherein any of said pyrrole-moieties, pyrazole-moieties, imidazole-moieties and tetrazole-moieties is substituted at the carbon- atoms by 1 or 2 substituents independently selected from R6; and is substituted at one of the nitrogen atoms by one substituent selected from R7; wherein R6is selected from hydrogen, halogen, cyano, hydroxy, amino, Ci-C4-alkyl, C2-C4-alkenyl, C2- C4-alkynyl, Ci-C4-haloalkyl, Cs-Ce-cycloalkyl, Ci-C4-alkoxy, Ci-C4-alkylamino, di(Ci-C4-alkyl)amino, Ci-C4-haloalkoxy, Ci-C4-halosulfanyl, Cs-Ce-alkenyloxy, Cs-Ce-alkynyloxy, Cs-Ce-cycloalkyloxy, C1-C4- alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy, Ci-C4-alkylsulfanyl, Ci-C4-alkylsulfinyl, or C1-C4- alkylsulfonyl; and wherein R7is selected from hydrogen, or Ci-C4-alkyl; and

[0010] Z1is selected from Ci-Ce-alkyl, wherein said Ci-Ce-alkyl is unsubstituted or substituted with 1 , 2 or 3 substituents independently selected halogen, hydroxy, cyano, carboxy, Ci-C4-alkyl, Cs-Ce-alkenyl, C2-C6- alkynyl, Ci-C4-haloalkyl, Ci-C4-haloalkoxy, Ci-C4-alkoxy, Cs-Ce-alkenyloxy, Cs-Ce-alkynyloxy, C1-C4- alkylsulfanyl, Ci-C4-alkylsulfinyl, Ci-C4-alkylsulfonyl, Ci-C4-haloalkylsulfanyl, Ci-C4-halkoalkylsulfinyl, C1-C4- haloalkylsulfonyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy, Ci-C4-alkylcarbonyl, C1-C4- alkoxycarbonyl, N-Ci-C4-alkoxy-C-Ci-C4-alkyl-carbonimidoyl, N-hydroxy-C-Ci-C4-alkyl-carbonimidoyl, trifluoromethylsulfonyloxy, phenyl, a 5- to 6-membered saturated, partially saturated or aromatic heteroaryl, or Cs-Ce-cycloalkyl; wherein any of said heteroaryl contains 1 , 2 or 3 heteroatoms independently selected from O, S, or N, with the proviso that only one is selected from O or S; wherein any of said phenyl, 5- to 6-membered saturated, partially saturated or aromatic heteroaryl, are unsubstituted or substituted with 1 , 2 or 3 substituents independently selected from halogen, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, or Ci-C4-alkoxy; and wherein said Cs-Ce-cycloalkyl is unsubstituted or substituted with 1 , 2 or 3 substituents independently selected from halogen, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, or Ci-C4-alkoxy; or an agrochemically acceptable salt, or N-oxide thereof.

[0011] Surprisingly, it has been found that the compounds of formula (I) have, for practical purposes, a very advantageous level of biological activity for protecting plants against diseases that are caused by fungi.

[0012] According to a second aspect of the invention, there is provided an agrochemical composition comprising a fungicidally effective amount of a compound of formula (I) according to the invention. Such an agricultural composition may further comprise at least one additional active ingredient and / or an agrochemically-acceptable diluent or carrier.

[0013] According to a third aspect of the invention, there is provided a method of controlling or preventing infestation of useful plants by phytopathogenic microorganisms, wherein a fungicidally effective amount of a compound of formula (I) according to the invention, or a composition comprising the compound of formula (I), is applied to the plants, to parts thereof or the locus thereof.

[0014] According to a fourth aspect of the invention, there is provided the use of a compound of formula (I) according to the invention as a fungicide. According to this particular aspect of the invention, the use may exclude methods for treatment of the human or animal body by surgery or therapy and diagnostic methods practiced on the human or animal body. The presence of one or more possible asymmetric carbon atoms in a compound of formula (I) according to the invention means that the compounds may occur in chiral isomeric forms, i.e., enantiomeric or diastereomeric forms. Also, atropisomers may occur as a result of restricted rotation about a single bond. Formula (I) is intended to include all those possible isomeric forms and mixtures thereof. The present invention includes all those possible isomeric forms and mixtures thereof for a compound of formula (I) according to the invention. Likewise, a compound of formula (I) is intended to include all possible tautomers (including lactam-lactim tautomerism and keto-enol tautomerism) where present. The present invention includes all possible tautomeric forms for a compound of formula (I) according to the invention.

[0015] In each case, the compounds of formula (I) according to the invention are in free form, in oxidized form as an N-oxide, in covalently hydrated form, or in salt form, e.g., an agronomically usable or agrochemically acceptable salt form. N-oxides are oxidized forms of tertiary amines or oxidized forms of nitrogen containing heteroaromatic compounds. They are described for instance in the book “Heterocyclic N-oxides” by A. Albini and S. Pietra, CRC Press, Boca Raton 1991. N-oxides can be prepared by reacting a compound of formula (I) with a suitable oxidizing agent, for example the H2O2 / urea adduct, in the presence of an acid anhydride, e.g., trifluoroacetic anhydride. Such oxidations are known from the literature, for example from J. Med. Chem. 1989, 32 (12), 2561- 73, or W02000 / 15615. The compounds of formula (I) according to the invention also include hydrates, which may be formed during salt formation.

[0016] As used herein, the term "halogen" or “halo” refers to fluorine (fluoro), chlorine (chloro), bromine (bromo) or iodine (iodo), preferably fluorine, chlorine, or bromine. This also applies, correspondingly, to halogen in combination with other meanings, such as haloalkyl, haloalkenyl, haloalkynyl, haloalkoxy, and halocycloalkyl.

[0017] As used herein, amino means a -NH2 group.

[0018] As used herein, cyano means a -CN group.

[0019] As used herein, the term “hydroxyl” or “hydroxy” means an -OH group.

[0020] As used herein, the term “carboxylic acid” means a -COOH group.

[0021] As used herein, the term "Ci-Cn-alkyl” refers to a saturated straight- or branched hydrocarbon chain having 1 to n carbon atoms. Examples include but are not limited to methyl, ethyl, n-propyl, 1 -methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1 -ethylpropyl, n-hexyl, n-pentyl, 1 ,1 -dimethylpropyl, 1 ,2-dimethylpropyl.

[0022] As used herein, the term “C2-Cn-alkenyl” refers to an unsaturated straight or branched hydrocarbon chain having from two to n carbon atoms and comprising at least one double bond that can be of either the (Z) or (E) configuration. Examples include but are not limited to ethenyl (or vinyl), prop-1 -enyl, prop-2-enyl (or allyl), prop- 1-en-2-yl (or isopropenyl), but-2-enyl. Analogously, the term “Cs-Cn-alkenyl” refers to an unsaturated straight or branched hydrocarbon chain having from three to n carbon atoms.

[0023] As used herein, the term “C2-Cn-alkynyl” refers to a straight or branched hydrocarbon chain having from two to n carbon atoms and comprising at least one triple bond. Examples include but are not limited to ethynyl, prop- 2-ynyl (or propargyl), or but-3-ynyl. Analogously, the term “Cs-Cn-alkynyl” refers to a straight or branched hydrocarbon chain having from three to n carbon atoms and comprising at least one triple bond.

[0024] As used herein, the term “Cs-Cn-cycloalkyl” refers to a saturated, monovalent, monocyclic hydrocarbon ring which contains 3 to n carbon atoms. Examples include but are not limited to cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

[0025] As used herein, the term “cyano-Ci-Cn-alkyl” refers to Ci-Cn-alkyl as defined herein, in which at least one hydrogen atom is replaced with a cyano group, for example, cyano-methyl, 2-cyano-ethyl, 2-cyano-propyl, 3- cyano-propyl, 1-(cyano-methyl)-2-ethyl, 1-(methyl)-2-cyano-ethyl, 4-cyanobutyl.

[0026] As used herein, the term "Ci-Cn-alkoxy" refers to groups of the formula -O-(Ci-Cn-alkyl), in which the term “Ci- Cn-alkyl” is as defined herein. Examples include but are not limited to methoxy, ethoxy, n-propoxy, 1- methylethoxy, n-butoxy, 1 -methyl propoxy, 2-methylpropoxy or 1 ,1-dimethylethoxy.

[0027] As used herein, the term “C2-Cn-alkenyloxy” refers to groups of the formula -O-(C2-Cn-alkenyl), in which the term “C2-Cn-alkenyl” is as defined herein. Analogously, the term “Cs-Cn-alkenyloxy” as used herein to a group of the formula -O-(C3-Cn-alkenyl), in which the term “Cs-Cn-alkenyl” is as defined herein.

[0028] As used herein, the term "C2-Cn-alkynyloxy" refers to groups of the formula -O-(C2-Cn-alkynyl), in which the term “C2-Cn-alkynyl” is as defined herein. Analogously, the term “Cs-Cn-alkynyloxy” as used herein to a group of the formula -O-(C3-Cn-alkynyl), in which the term “Cs-Cn-alkynyl” is as defined herein.

[0029] As used herein, the term “Ci-Cn-alkoxy-Ci-Cn-alkyl” refers to a group of the formula -(Ci-Cn-alkyl)-O-(Ci-Cn- alkyl), in which each term “Ci-Cn-alkyl”, which may be the same or different, is as defined herein. Examples include, but are not limited to methoxymethyl, methoxyethyl, ethoxymethyl or propoxymethyl.

[0030] As used herein, the term “Ci-Cn-alkoxy-Ci-Cn-alkoxy” refers to a group of the formula -O-(Ci-Cn-alkyl)-O-(Ci- Cn-alkyl), in which each term “Ci-Cn-alkyl”, which may be the same or different, is as defined herein.

[0031] As used herein, the term “Ci-Cn-alkyl-Ci-Cn-alkoxy-Ci-Cn-alkoxy” refers to a radical of the formula -Ra-ORb- ORc, where Rais a Ci-Cn-alkyl group as defined above, and Rb and Rcrefer to an Ci-Cn-alkyl group as defined above.

[0032] As used herein, the term “Cs-Cn-cycloalkyl-Ci-Cn-alkyl” refers to an alkyl radical (as mentioned above) substituted with a Cs-Cn-cycloalkyl group. Examples are cyclopropylmethyl, cyclopropylethyl.

[0033] As used herein, the term "Ci-Cn-haloalkyl" refers to a "Ci-Cn-alkyl” as defined herein, in which one or more hydrogen atoms may be replaced with one or more halogen atoms that may be the same or different. Examples include but are not limited to chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2- bromoethyl, 2-iodoethyl, 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. Analogously, the term “Ci-Cn-haloalkoxy” as used herein refers to an Ci-Cn-alkoxyl group as defined herein substituted with one or more halogen atoms which may be the same or different. As used herein, the term “Ci-Cn-alkylthio“ or “Ci-Cn-alkylsulfanyl“refers to a Ci-Cn-alkyl group linked through a sulfur atom.

[0034] As used herein, the term “Ci-Cn-haloalkylthio“ or “Ci-Cn-haloalkylsulfanyl“refers to a Ci-Cn-haloalkyl group linked through a sulfur atom.

[0035] As used herein, the term “Ci-Cn-alkylsulfinyl“ refers to a Ci-Cn-alkyl group linked through the sulfur atom of a sulfinyl (or S(=O)-) group.

[0036] As used herein, the term “Ci-Cn-alkylsulfonyl“ refers to a Ci-Cn-alkyl group linked through the sulfur atom of a sulfonyl (or S(=O)2-) group.

[0037] As used herein, the term “Ci-Cn-alkylcarbonyl” refers to a group of the formula -C(=O)-(Ci-Cn-alkyl), in which the term “Ci-Cn-alkyl” is as defined herein.

[0038] As used herein, the term “Ci-Cn-alkoxycarbonyl” refers to a group of the formula -C(=O)-O-(Ci-Cn-alkyl), in which the term “Ci-Cn-alkyl” is as defined herein.

[0039] As used herein, the term “Ci-Cn-alkoxycarbonyl-Ci-C4-alkyl” refers to a group of the formula -(Ci-Cn-alkyl)- C(=O)-O-(Ci-Cn-alkyl), in which the term “Ci-Cn-alkyl” is as defined herein.

[0040] As used herein, the term “Ci-Cn-alkylaminocarbonyl” refers to a Ci-Cn-alkylamino group (or RaNHC(=O)-), wherein Rais a Ci-Cn-alkyl group linked through the carbon atom of a carbonyl (C=O) group.

[0041] As used herein, the term “aminocarbonyl-Ci-Cn-alkyl” refers to a Ci-Cn-alkyl radical substituted by an aminocarbonyl (or NH2C(=O)-) group.

[0042] As used herein, the term “Ci-Cn-alkylaminocarbonyl-Ci-Cn-alkyl” refers to a Ci-Cn-alkyl radical substituted by a C-i-Cn-alkylaminocarbonyl (or RaNHC(=O)-) group, wherein Rais a Ci-Cn-alkyl group. The Ci-Cn-alkyl group linked to the nitrogen may be substituted.

[0043] As used herein, the term “N-Ci-Cn-alkylamino” refers to a group of the formula -NH-(Ci-Cn-alkyl), in which the term “Ci-Cn-alkyl” is as defined herein.

[0044] As used herein, the term "N,N-di(Ci-Cn-alkyl)amino" refers to a group of the formula -N-(Ci-Cn-alkyl)2, in which each term “Ci-Cn-alkyl”, which may be the same or different, is as defined herein.

[0045] As used herein the term “5- or 6-membered heteroaryl” refers to a 5- or 6-membered monocyclic, aromatic ring system containing 1 , 2, or 3 heteroatoms independently selected from the group consisting of oxygen, nitrogen and sulfur. In the 6-membered heteroaryl rings the heteroatom ring members can only be nitrogen atoms. Examples of 5-membered heteroaryl include but are not limited to furyl (furanyl), thienyl, pyrrolyl, pyrazolyl, imidazolyl, isooxazolyl. Examples of 6-membered heteroaryl include but are not limited to pyridyl (or pyridinyl), pyridazinyl, pyrimidinyl.

[0046] Unless defined otherwise, the definitions for collective terms also apply to these collective terms in composite moieties. For example, the terms “Ci-Cn-alkoxycarbonyl-Ci-Cn-alkyl”, “Ci-Cn- alkylcarbonyloxy-Ci-Cn-alkyl”, “Ci-Cn-alkylcarbonylamino-Ci-Cn-alkyl”, “N,N-di(Ci-Cn-alkyl)amino-Ci-Cn -alkyl” and “N-(Ci-Cn-alkyl)amino-Ci- Cn-alky I” as used herein refer a “Ci-Cn-alkyl” as defined herein, wherein one hydrogen atom is replaced with a Ci-Cn-alkoxycarbonyl, Ci-Cn-alkylcarbonyloxy, C-i-Cn-alkylcarbonylamino, N,N-di(Ci-Cn-alkyl)amino, or N-(Ci- C4-alkyl)amino group as defined herein respectively.

[0047] As used herein, the term "controlling" refers to reducing the number of pests, eliminating pests and / or preventing further pest damage such that damage to a plant or to a plant derived product is reduced.

[0048] As used herein, the term "pest" refers to insects, and molluscs that are found in agriculture, horticulture, forestry, the storage of products of vegetable origin (such as fruit, grain, and timber); and those pests associated with the damage of man-made structures. The term pest encompasses all stages in the life cycle of the pest.

[0049] As used herein, the term "effective amount" refers to the amount of the compound, or a salt thereof, which, upon single or multiple applications provides the desired effect.

[0050] An effective amount is readily determined by the skilled person in the art, using known techniques and by observing results obtained under analogous circumstances. In determining the effective amount, a number of factors are considered including, but not limited to the type of plant or derived product to be applied; the pest to be controlled and its lifecycle; the particular compound applied; the type of application; and other relevant circumstances.

[0051] As used herein, the term “room temperature” or “RT” or “rt” or “ambient temperature” refer to a temperature of about 15°C to about 35°C. For example, rt can refer to a temperature of about 20°C to about 30°C.

[0052] The following list provides definitions, including preferred definitions, for substituents R1, R2, R3, R4, R5, R6, R7, Q and Z1with reference to the compounds of formula (I) of the present invention. For any one of these substituents, any of the definitions given below may be combined with any definition of any other substituent given below or elsewhere in this document.

[0053] In one embodiment of the invention, R1is selected from hydrogen, halogen, cyano, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkyl, Cs-Ce-cycloalkyl, Ci-C4-alkylsulfanyl, Ci-C4-alkylsulfinyl, or Ci-C4-alkylsulfonyl. In another embodiment, R1is hydrogen, halogen, cyano, Ci-Cs-alkyl, Ci-Cs-alkoxy, Ci-C2-haloalkyl, Cs-Ce-cycloalkyl, Ci- C2-alkylsulfanyl, Ci-C2-alkylsulfi nyl, or Ci-C2-alkylsulfonyl. In still another embodiment of the invention, R1is hydrogen, halogen, Ci-Cs-alkyl, Ci-C2-haloalkyl, or Cs-Ce-cycloalkyl. Preferably, R1is hydrogen, halogen, Ci- Cs-alkyl, or Cs-Ce-cycloalkyl. More preferably, R1is hydrogen, chlorine, bromine, fluorine, methyl, ethyl or cyclopropyl. Even more preferably, R1is hydrogen, chlorine, methyl, or cyclopropyl. Still even more preferably, R1is hydrogen.

[0054] In one embodiment of the invention, R2is selected from hydrogen, halogen, cyano, or Ci-C4-alkyl. Preferably, R2is hydrogen, halogen, cyano, or Ci-Cs-alkyl. More preferably, R2is hydrogen, chlorine, bromine, fluorine, cyano, methyl, or ethyl. Even more preferably, R2is hydrogen, chlorine, cyano, or methyl. Still even more preferably, R2is hydrogen. In one embodiment of the invention, B1is selected from CR4, or N. In one embodiment, B1is CR4. in another embodiment, B1is N.

[0055] In one embodiment of the invention, B2is selected from CR5, or N. In one embodiment, B2is CR5. in another embodiment, B2is N.

[0056] In another embodiment of the invention, B1is N, and B2is CR5; or B1is CR4and B2is N; or B1is CR4and B2is CR5.

[0057] In one embodiment of the invention, R3, R4and R5are independently selected from hydrogen, halogen, cyano, hydroxy, amino, carboxy, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-haloalkoxy, Ci-C4-alkoxy, Cs-Ce-alkenyloxy, C3- Ce-alkynyloxy, Ci-C4-alkylsulfanyl, Ci-C4-alkylsulfinyl, Ci-C4-alkylsulfonyl, Ci-C4-alkoxy-Ci-C4-alkyl, C1-C4- alkoxy-Ci-C4-alkoxy, Ci-C4-alkoxycarbonyl, Ci-C4-alkylcarbonyl, carbamoyl, Ci-C4-alkylaminocarbonyl, di(Ci- C6-alkyl)aminocarbonyl, cyano-Ci-C4-alkyl, N-Ci-C4-alkoxy-C-Ci-C4-alkyl-carbonimidoyl, N-hydroxy-C-Ci-C4- alkyl-carbonimidoyl, Ci-C4-alkylamino, Ci-C4-dialkylamino, Ci-C4-alkylaminocarbonyl, C1-C4- dialkylaminocarbonyl, trifluoromethylsulfonyloxy, phenyl, a 5- to 6-membered saturated, partially saturated or aromatic heteroaryl, or Cs-Ce-cycloalkyl; wherein any of said heteroaryl contains 1 , 2 or 3 heteroatoms independently selected from O, S, or N, with the proviso that only one is selected from O or S; wherein any of said phenyl and 5- to 6-membered saturated, partially saturated or aromatic heteroaryl are unsubstituted or substituted with 1 , 2, or 3 substituents independently selected from halogen, cyano, Ci-C4-alkyl, C1-C4- haloalkyl, or Ci-C4-alkoxy; and wherein said Cs-Ce-cycloalkyl is unsubstituted or substituted with 1 , 2 or 3 substituents independently selected from halogen, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, or Ci-C4-alkoxy.

[0058] In one embodiment of the invention, R3is selected from hydrogen, halogen, cyano, hydroxy, amino, carboxy, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-haloalkoxy, Ci-C4-alkoxy, Cs-Ce-alkenyloxy, Cs-Ce-alkynyloxy, C1-C4- alkylsulfanyl, Ci-C4-alkylsulfinyl, Ci-C4-alkylsulfonyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy, C1- C4-alkoxycarbonyl, Ci-C4-alkylcarbonyl, carbamoyl, Ci-C4-alkylaminocarbonyl, di(Ci-C6-alkyl)aminocarbonyl, cyano-Ci-C4-alkyl, N-Ci-C4-alkoxy-C-Ci-C4-alkyl-carbonimidoyl, N-hydroxy-C-Ci-C4-alkyl-carbonimidoyl, C1- C4-alkylamino, Ci-C4-dialkylamino, Ci-C4-alkylaminocarbonyl, Ci-C4-dialkylaminocarbonyl, trifluoromethylsulfonyloxy, phenyl, a 5- to 6-membered saturated, partially saturated or aromatic heteroaryl, or Cs-Ce-cycloalkyl; wherein any of said heteroaryl contains 1 , 2 or 3 heteroatoms independently selected from O, S, or N, with the proviso that only one is selected from O or S; wherein any of said phenyl and 5- to 6- membered saturated, partially saturated or aromatic heteroaryl are unsubstituted or substituted with 1 , 2, or 3 substituents independently selected from halogen, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, or Ci-C4-alkoxy; and wherein said Cs-Ce-cycloalkyl is unsubstituted or substituted with 1 , 2 or 3 substituents independently selected from halogen, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, or Ci-C4-alkoxy. In another embodiment of the invention, R3is hydrogen, halogen, hydroxy, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C1-C4- alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy, Ci-C4-alkoxycarbonyl, Ci-C4-alkylcarbonyl, Cs-Ce-cycloalkyl; and wherein said Cs-Ce-cycloalkyl is unsubstituted or substituted with 1 , 2 or 3 substituents independently selected from halogen, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, or Ci-C4-alkoxy. Preferably, R3is hydrogen, halogen, cyano, Ci-Cs-alkyl, Ci-Cs-haloalkyl, Ci-Cs-alkoxy, Ci-C2-haloalkoxy, Ci-C2-alkoxy-Ci-Cs-alkyl, C1-C2- alkoxy-Ci-C2-alkoxy, Ci-C2-alkoxycarbonyl, Ci-C2-alkylcarbonyl, or Cs-Ce-cycloalkyl; and wherein said C3-C6- cycloalkyl is unsubstituted or substituted with 1 substituent selected from halogen, cyano, Ci-C2-alkyl, C1-C2- haloalkyl, or Ci-C2-alkoxy. More preferably, R3is hydrogen, halogen, cyano, Ci-Cs-alkyl, or Cs-Ce-cycloalkyl. Even more preferably, R3is hydrogen, chlorine, bromine, fluorine, cyano, methyl, or cyclopropyl. In another embodiment, R3is hydrogen.

[0059] In one embodiment of the invention, R4and R5are independently selected from hydrogen, halogen, cyano, hydroxy, amino, carboxy, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-haloalkoxy, Ci-C4-alkoxy, Cs-Cs-alkenyloxy, C3-C6- alkynyloxy, Ci-C4-alkylsulfanyl, Ci-C4-alkylsulfinyl, Ci-C4-alkylsulfonyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy- Ci-C4-alkoxy, Ci-C4-alkoxycarbonyl, Ci-C4-alkylcarbonyl, carbamoyl, Ci-C4-alkylaminocarbonyl, di(Ci-Ce- alkyl)aminocarbonyl, cyano-Ci-C4-alkyl, N-Ci-C4-alkoxy-C-Ci-C4-alkyl-carbonimidoyl, N-hydroxy-C-Ci-C4- alkyl-carbonimidoyl, Ci-C4-alkylamino, Ci-C4-dialkylamino, Ci-C4-alkylaminocarbonyl, C1-C4- dialkylaminocarbonyl, trifluoromethylsulfonyloxy, phenyl, a 5- to 6-membered saturated, partially saturated or aromatic heteroaryl, or Cs-Ce-cycloalkyl; wherein any of said heteroaryl contains 1 , 2 or 3 heteroatoms independently selected from O, S, or N, with the proviso that only one is selected from O or S; wherein any of said phenyl and 5- to 6-membered saturated, partially saturated or aromatic heteroaryl are unsubstituted or substituted with 1 , 2, or 3 substituents independently selected from halogen, cyano, Ci-C4-alkyl, C1-C4- haloalkyl, or Ci-C4-alkoxy; and wherein said Cs-Ce-cycloalkyl is unsubstituted or substituted with 1 , 2 or 3 substituents independently selected from halogen, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, or Ci-C4-alkoxy.

[0060] In another embodiment of the invention, R4and R5are independently selected from hydrogen, halogen, cyano, hydroxy, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-haloalkoxy, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy- Ci-C4-alkoxy, Ci-C4-alkoxycarbonyl, Ci-C4-alkylcarbonyl, or Cs-Ce-cycloalkyl; and wherein said C3-C6- cycloalkyl is unsubstituted or substituted with 1 , 2 or 3 substituents independently selected from halogen, C1- C4-alkyl, Ci-C4-haloalkyl, or Ci-C4-alkoxy. Preferably, R4and R5are independently selected from hydrogen, halogen, cyano, Ci-Cs-alkyl, Ci-C2-haloalkyl, Ci-Cs-alkoxy, Ci-C2-haloalkoxy, Ci-C2-alkoxy-Ci-C3-alkyl, C1-C2- alkoxy-Ci-C2-alkoxy, Ci-C2-alkoxycarbonyl, Ci-C2-alkylcarbonyl, or Cs-Ce-cycloalkyl; and wherein said C3-C6- cycloalkyl is unsubstituted or substituted with 1 substituent selected from halogen, cyano, Ci-C2-alkyl, C1-C2- haloalkyl, or Ci-C2-alkoxy. More preferably, R4and R5are independently selected from hydrogen, halogen, cyano, Ci-Cs-alkyl, Ci-Cs-alkoxy, Ci-C2-haloalkyl, Ci-C2-haloalkoxy, Ci-C2-alkoxy-Ci-C3-alkyl, Ci-C2-alkoxy-Ci- C2-alkoxy, Ci-C2-alkoxycarbonyl, or C3-C4-cycloalkyl; and wherein said C3-C4-cycloalkyl is unsubstituted or substituted with 1 substituent selected from cyano or methyl. Even more preferably, R4and R5are independently selected from hydrogen, cyano, chlorine, bromine, fluorine, methyl, difluoromethyl, difluoromethoxy, 2,2,2-trifluoroethoxy, 2,2-difluoroethoxy, methoxy, 2-methoxyethoxy, methoxycarbonyl, or cyclopropyl. In another embodiment, R4and R5are independently selected from hydrogen, halogen, cyano, Ci-Cs-alkyl, Ci-Cs-alkoxy, Ci-C2-alkoxycarbonyl, or C3-C4-cycloalkyl. Preferably, R4and R5are independently selected from hydrogen, chlorine, bromine, cyano, methyl, methoxy, methoxycarbonyl, or cyclopropyl. More preferably, R4and R5are independently selected from hydrogen, cyano, or cyclopropyl. Even more preferably, R4and R5are independently selected from hydrogen, or cyano. In one embodiment of the invention, R4is selected from hydrogen, halogen, cyano, hydroxy, Ci-C4-alkyl, Ci- C4-haloalkyl, Ci-C4-haloalkoxy, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy, C1-C4- alkoxycarbonyl, Ci-C4-alkylcarbonyl, or Cs-Ce-cycloalkyl; and wherein said Cs-Ce-cycloalkyl is unsubstituted or substituted with 1 , 2 or 3 substituents independently selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, or C1- C4-alkoxy. Preferably, R4is hydrogen, halogen, cyano, Ci-Cs-alkyl, Ci-C2-haloalkyl, Ci-Cs-alkoxy, C1-C2- haloalkoxy, Ci-C2-alkoxy-Ci-C3-alkyl, Ci-C2-alkoxy-Ci-C2-alkoxy, Ci-C2-alkoxycarbonyl, Ci-C2-alkylcarbonyl, or C3-C4-cycloalkyl; and wherein said C3-C4-cycloalkyl is unsubstituted or substituted with 1 substituent selected from halogen, cyano, Ci-C2-alkyl, Ci-C2-haloalkyl, or Ci-C2-alkoxy. More preferably, R4is hydrogen, halogen, cyano, Ci-Cs-alkyl, Ci-Cs-alkoxy, Ci-C2-haloalkyl, Ci-C2-haloalkoxy, Ci-C2-alkyoxy-Ci-C3-alkyl, Ci-C2-alkoxy- Ci-C2-alkoxy, Ci-C2-alkoxycarbonyl, or C3-C4-cycloalkyl; and wherein said C3-C4-cycloalkyl is unsubstituted or substituted with 1 substituent selected from cyano or methyl. Even more preferably, R4is hydrogen, cyano, chlorine, bromine, fluorine, methyl, difluoromethyl, difluoromethoxy, 2,2,2-trifluoroethoxy, 2,2-difluoroethoxy, methoxy, 2-methoxyethoxy, methoxycarbonyl, or cyclopropyl.

[0061] In another embodiment, R4is hydrogen, halogen, cyano, Ci-Cs-alkyl, Ci-Cs-alkoxy, Ci-C2-alkoxycarbonyl, or C3-C4-cycloalkyl. Preferably, R4is hydrogen, chlorine, bromine, cyano, methyl, methoxy, methoxycarbonyl, or cyclopropyl. More preferably, R4is hydrogen, cyano, or cyclopropyl. Even more preferably, R4is hydrogen, or cyano.

[0062] In one embodiment of the invention, R5is selected from hydrogen, halogen, cyano, hydroxy, Ci-C4-alkyl, C1- C4-haloalkyl, Ci-C4-haloalkoxy, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy, C1-C4- alkoxycarbonyl, Ci-C4-alkylcarbonyl, or Cs-Ce-cycloalkyl; and wherein said Cs-Ce-cycloalkyl is unsubstituted or substituted with 1 , 2 or 3 substituents independently selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, or C1- C4-alkoxy. Preferably, R5is hydrogen, halogen, cyano, Ci-Cs-alkyl, Ci-C2-haloalkyl, Ci-Cs-alkoxy, C1-C2- haloalkoxy, Ci-C2-alkoxy-Ci-C3-alkyl, Ci-C2-alkoxy-Ci-C2-alkoxy, Ci-C2-alkoxycarbonyl, Ci-C2-alkylcarbonyl, or C3-C4-cycloalkyl; and wherein said C3-C4-cycloalkyl is unsubstituted or substituted with 1 substituent selected from halogen, cyano, Ci-C2-alkyl, Ci-C2-haloalkyl, or Ci-C2-alkoxy. More preferably, R5is hydrogen, halogen, cyano, Ci-Cs-alkyl, Ci-Cs-alkoxy, Ci-C2-haloalkyl, Ci-C2-haloalkoxy, Ci-C2-alkoxy-Ci-C3-alkyl, Ci-C2-alkoxy- Ci-C2-alkoxy, Ci-C2-alkoxycarbonyl, or C3-C4-cycloalkyl; and wherein said C3-C4-cycloalkyl is unsubstituted or substituted with 1 substituent selected from cyano or methyl. Even more preferably, R5is hydrogen, cyano, chlorine, bromine, fluorine, methyl, difluoromethyl, difluoromethoxy, 2,2,2-trifluoroethoxy, 2,2-difluoroethoxy, methoxy, 2-methoxyethoxy, methoxycarbonyl, or cyclopropyl.

[0063] In another embodiment, R5is hydrogen, halogen, cyano, Ci-Cs-alkyl, Ci-Cs-alkoxy, Ci-C2-alkoxycarbonyl, or C3-C4-cycloalkyl. Preferably, R5is hydrogen, chlorine, bromine, cyano, methyl, methoxy, methoxycarbonyl, or cyclopropyl. More preferably, R5is hydrogen, cyano, or cyclopropyl. Even more preferably, R5is hydrogen, or cyano.

[0064] In one embodiment of the invention, Q is a 5-membered aromatic heteroaryl, wherein said 5-membered aromatic heteroaryl is selected from pyrrol-1 -yl, pyrrol-2-yl, pyrrol-3-yl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-5-yl, imidazole-1-yl, imidazole2-yl, imidazole-4-yl, triazol-1 -yl, triazol-2-yl, triazol-4-yl, 1 ,2,4-triazol-1 -yl, 1 ,2,4-triazol- 3-yl, or tetrazol-5-yl; wherein any of said pyrrole-moieties, pyrazole-moieties, imidazole-moieties and tetrazole- moieties is substituted at the carbon-atoms by 1 or 2 substituents independently selected from R6; and is substituted at one of the nitrogen atoms by one substituent selected from R7; wherein R6is selected from hydrogen, halogen, cyano, hydroxy, amino, Ci-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, Ci-C4-haloalkyl, C3-C6- cycloalkyl, Ci-C4-alkoxy, Ci-C4-alkylamino, di(Ci-C4-alkyl)amino, Ci-C4-haloalkoxy, Ci-C4-halosulfanyl, C3-C6- alkenyloxy, Cs-Ce-alkynyloxy, Cs-Ce-cycloalkyloxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy, C1- C4-alkylsulfanyl, Ci-C4-alkylsulfi nyl, or Ci-C4-alkylsulfonyl; and R7is selected from hydrogen, or Ci-C4-alkyl.

[0065] Preferably, Q is a 5-membered aromatic heteroaryl, wherein said 5-membered aromatic heteroaryl is selected from pyrrol-1 -yl, pyrrol-2-yl, pyrrol-3-yl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-5-yl, imidazole-1-yl, imidazole2-yl, imidazole-4-yl, triazol-1 -yl, triazol-2-yl, triazol-4-yl, 1 ,2,4-triazol-1 -yl, 1 ,2,4-triazol-3-yl, or tetrazol-5-yl; wherein any of said pyrrole-moieties, pyrazole-moieties, imidazole-moieties and tetrazole-moieties is substituted at the carbon-atoms by 1 or 2 substituents independently selected from R6; and is substituted at one of the nitrogen atoms by one substituent selected from R7; wherein R6is hydrogen, halogen, cyano, Ci-Cs-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, Ci-C2-haloalkyl, Cs-Ce-cycloalkyl, Ci-Cs-alkoxy, Ci-Cs-alkylamino, di(Ci-C3-alkyl)amino, C1-C2- haloalkoxy, Ci-C2-halosulfanyl, Cs-Cs-alkenyloxy, Cs-Ce-alkynyloxy, Cs-Ce-cycloalkyloxy, Ci-C2-alkoxy-Ci-C2- alkyl, Ci-C2-alkoxy-Ci-C2-alkoxy, Ci-C2-alkylsulfanyl, Ci-C2-alkylsulfinyl, or Ci-C2-alkylsulfonyl; and R7is hydrogen or Ci-Cs-alkyl. More preferably, Q is a 5-membered aromatic heteroaryl, wherein said 5-membered aromatic heteroaryl is selected from pyrrol-1 -yl, pyrrol-2-yl, pyrrol-3-yl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-5-yl, imidazole-1-yl, imidazole2-yl, imidazole-4-yl, triazol-1 -yl, triazol-2-yl, triazol-4-yl, 1 ,2,4-triazol-1 -yl, 1 ,2,4-triazol- 3-y I , or tetrazol-5-yl; wherein any of said pyrrole-moieties, pyrazole-moieties, imidazole-moieties and tetrazole- moieties is substituted at the carbon-atoms by 1 or 2 substituents independently selected from R6; and is substituted at one of the nitrogen atoms by one substituent selected from R7; wherein R6is hydrogen, halogen, cyano, Ci-Cs-alkyl, Ci-Cs-alkoxy, Ci-C2-haloalkyl, Ci-C2-haloalkoxy, Ci-C2-alkoxy-Ci-C2-alkyl, C1-C3- alkylamino, di(Ci-C3-alkyl)amino, Ci-C2-alkylsulfanyl, Ci-C2-alkylsulfinyl, or Ci-C2-alkylsulfonyl; and R7is hydrogen or Ci-Cs-alkyl. Even more preferably, Q is a 5-membered aromatic heteroaryl, wherein said 5- membered aromatic heteroaryl is selected from pyrrol-1 -yl, pyrrol-2-yl, pyrrol-3-yl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-5-yl, imidazole-1-yl, imidazole2-yl, imidazole-4-yl, triazol-1 -yl, triazol-2-yl, triazol-4-yl, 1 ,2,4-triazol-1 -yl, 1 ,2,4-triazol-3-yl, or tetrazol-5-yl; wherein any of said pyrrole-moieties, pyrazole-moieties, imidazole-moieties and tetrazole-moieties is substituted at the carbon-atoms by 1 or 2 substituents independently selected from R6; and is substituted at one of the nitrogen atoms by one substituent selected from R7; wherein R6is hydrogen, halogen, Ci-Cs-alkyl, Ci-Cs-alkoxy, or Ci-C2-alkylsulfanyl; and R7is hydrogen or methyl.

[0066] In another embodiment of the invention, Q is a 5-membered aromatic heteroaryl, wherein said 5-membered aromatic heteroaryl is selected from wherein the staggered line denotes the attachment point of the Q substituent to the rest of the molecule; R6a, R6b, R6cand R6dare independently selected from hydrogen, halogen, Ci-Cs-alkyl, Ci-Cs-alkoxy, or C1-C2- alkylsu Ifanyl; and R7is hydrogen or methyl. In another embodiment of the invention, Q is a 5-membered aromatic heteroaryl, wherein said 5-membered aromatic heteroaryl is selected from wherein the staggered line denotes the attachment point of the Q substituent to the rest of the molecule; R6a, R6t>, R6canc| R6dareindependently selected from hydrogen, halogen, Ci-Cs-alkyl, Ci-Cs-alkoxy, or C1-C2- alkylsulfanyl; and R7is hydrogen or methyl. In another embodiment, Q is a 5-membered aromatic heteroaryl, wherein said 5-membered aromatic heteroaryl is selected from wherein the staggered line denotes the attachment point of the Q substituent to the rest of the molecule; R6a, R6b, R6cand R6dare independently selected from hydrogen, hydrogen, chloro, methyl, methoxy, or methylsulfanyl; and R7is hydrogen or methyl.

[0067] In another embodiment, Q is a 5-membered aromatic heteroaryl, wherein said 5-membered aromatic heteroaryl is selected from wherein the staggered line denotes the attachment point of the Q substituent to the rest of the molecule; R6a, R6b, R6cand R6dare independently selected from hydrogen, hydrogen, chloro, methyl, methoxy, or methylsulfanyl; and R7is hydrogen or methyl.

[0068] In another preferred embodiment, Q is a 5-membered aromatic heteroaryl, wherein said 5-membered aromatic heteroaryl is selected from wherein the staggered line denotes the attachment point of the Q-substituent to the rest of the molecule; R6a, R6t>, R6Canc| R6dareindependently selected from hydrogen, halogen, Ci-Cs-alkyl, Ci-Cs-alkoxy, or C1-C2- alkylsu Ifanyl; and R7is hydrogen or methyl.

[0069] In another preferred embodiment, Q is a 5-membered aromatic heteroaryl, wherein said 5-membered aromatic heteroaryl is selected from wherein the staggered line denotes the attachment point of Q-substituent to the rest of the molecule; wherein R6a, R6b, R6cand R6dare independently selected from hydrogen, halogen, Ci-Cs-alkyl, Ci-Cs-alkoxy, or C1-C2- alkylsu Ifanyl; and R7is hydrogen or methyl.

[0070] In another preferred embodiment, Q is a 5-membered aromatic heteroaryl, wherein said 5-membered aromatic heteroaryl is selected from wherein the staggered line denotes the attachment point of Q-substituent to the rest of the molecule; wherein R6a, R6b, R6cand R6dare independently selected from hydrogen, chloro, methyl, or methoxy; and R7is hydrogen or methyl.

[0071] In one embodiment of the invention, Z1is selected from Ci-Ce-alkyl, wherein said Ci-Ce-alkyl is unsubstituted or substituted with 1 , 2 or 3 substituents independently selected from halogen, hydroxy, cyano, carboxy, C1- C4-alkyl, C2-Cs-alkenyl, C2-Ce-alkynyl, Ci-C4-haloalkyl, Ci-C4-haloalkoxy, Ci-C4-alkoxy, C2-Ce-alkenyloxy, C2- Ce-alkynyloxy, Ci-C4-alkylsulfanyl, Ci-C4-alkylsulfinyl, Ci-C4-alkylsulfonyl, Ci-C4-haloalkylsulfanyl, C1-C4- halkoalkylsulfinyl, Ci-C4-haloalkylsulfonyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy, C1-C4- alkylcarbonyl, Ci-C4-alkoxycarbonyl, N-Ci-C4-alkoxy-C-Ci-C4-alkyl-carbonimidoyl, N-hydroxy-C-Ci-C4-alkyl- carbonimidoyl, trifluoromethylsulfonyloxy, phenyl, a 5- to 6-membered saturated, partially saturated or aromatic heteroaryl, or Cs-Ce-cycloalkyl; wherein any of said heteroaryl contains 1 , 2 or 3 heteroatoms independently selected from O, S, or N, with the proviso that only one is selected from O or S; wherein any of said phenyl, 5- to 6-membered saturated, partially saturated or aromatic heteroaryl, are unsubstituted or substituted with 1 , 2 or 3 substituents independently selected from halogen, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, or Ci-C4-alkoxy; and wherein said Cs-Ce-cycloalkyl is unsubstituted or substituted with 1 , 2 or 3 substituents independently selected from halogen, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, or Ci-C4-alkoxy. In another embodiment of the invention, Z1is selected from Ci-Ce-alkyl, wherein said Ci-Ce-alkyl is unsubstituted or substituted with 1 , 2 or 3 substituents independently selected from halogen, cyano, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C2-C6- alkenyl, C2-Ce-alkynyl, C2-Cs-alkenyloxy, C2-Ce-alkynyloxy, Ci-C4-alkylsulfanyl, Ci-C4-alkylsulfonyl, or C3-C6- cycloalkyl; and wherein said Cs-Ce-cycloalkyl is unsubstituted or substituted with 1 substituent selected from halogen, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, or Ci-C4-alkoxy. Preferably, Z1is selected from Ci-Cs-alkyl, wherein said Ci-Cs-alkyl is unsubstituted or substituted with 1 , 2 or 3 substituents independently selected from halogen, cyano, Ci-C4-alkyl, Ci-C2-alkoxy, Ci-C2-haloalkoxy, C2-C3-alkenyl, C2-C3-alkynyl, C2-C3-alkenyloxy, C2-C3-alkynyloxy, Ci-C2-alkylsulfanyl, Ci-C2-alkylsulfonyl, or cyclopropyl; and wherein said cyclopropyl is unsubstituted or substituted with 1 substituent selected from halogen, cyano, Ci-Cs-alkyl, or Ci-C2-haloalkyl.

[0072] The present invention, accordingly, makes available a compound of formula (I) having R1, R2, R3, R4, R5, R6, R7, Q and Z1as defined above in all combinations / each permutation.

[0073] Embodiments according to the invention are provided as set out below.

[0074] In one embodiment of the invention, a compound of formula (I), wherein B1is CR4; B2is N; and wherein R1, R2, R3, R4, R6(R6a, R6b, R6cand R6d), R7, Q and Z1are defined as for compounds of formula (I).

[0075] In another embodiment of the invention, a compound of formula (I), wherein B1is CR4; B2is N; R1and R2are hydrogen; R3is hydrogen, halogen, cyano, Ci-Cs-alkyl, or Cs-Ce-cycloalkyl; and wherein R4, R6(R6a, R6b, R6cand R6d), R7, Q and Z1are defined as for compounds of formula (I).

[0076] In another embodiment of the invention, a compound of formula (I), wherein B1is CR4; B2is N; R1, R2are R3are hydrogen; and wherein R4, R6(R6a, R6b, R6cand R6d), R7, Q and Z1are defined as for compounds of formula (I).

[0077] In another embodiment of the invention, a compound of formula (I), wherein B1is CR4; B2is N; R1, R2are R3are hydrogen; R4is hydrogen, halogen, cyano, Ci-Cs-alkyl, Ci-Cs-alkoxy, Ci-C2-alkoxycarbonyl, or C3-C4- cycloalkyl; and wherein R6(R6a, R6b, R6cand R6d), R7, Q and Z1are defined as for compounds of formula (I).

[0078] In another embodiment of the invention, a compound of formula (I), wherein B1is CR4; B2is N; R1, R2are R3are hydrogen; R4is hydrogen, halogen, cyano, Ci-Cs-alkyl, Ci-Cs-alkoxy, Ci-C2-alkoxycarbonyl, or C3-C4- cycloalkyl; R6a, R6b, R6cand R6dare independently selected from hydrogen, halogen, Ci-Cs-alkyl, Ci-Cs-alkoxy, or Ci-C2-alkylsulfanyl; R7is hydrogen or Ci-Cs-alkyl; and wherein Q and Z1are defined as for compounds of formula (I).

[0079] In another embodiment of the invention, a compound of formula (I), wherein B1is CR4; B2is N; R1, R2are R3are hydrogen; R4is hydrogen, halogen, cyano, Ci-Cs-alkyl, Ci-Cs-alkoxy, Ci-C2-alkoxycarbonyl, or C3-C4- cycloalkyl; R6a, R6b, R6cand R6dare independently selected from hydrogen, halogen, Ci-Cs-alkyl, Ci-Cs-alkoxy, or Ci-C2-alkylsulfanyl; R7is hydrogen or Ci-Cs-alkyl; and wherein Q and Z1are defined as for compounds of formula (I).

[0080] In another embodiment of the invention, a compound of formula (I), wherein B1is CR4; B2is N; R1, R2are R3are hydrogen; R4is hydrogen, halogen, cyano, Ci-Cs-alkyl, Ci-Cs-alkoxy, Ci-C2-alkoxycarbonyl, or C3-C4- cycloalkyl; Q is a 5-membered aromatic heteroaryl, wherein said 5-membered aromatic heteroaryl is selected from wherein the staggered line denotes the attachment point of the Q substituent to the rest of the molecule; R6a, R6t>, R6Canc| R6dareindependently selected from hydrogen, halogen, Ci-Cs-alkyl, Ci-Cs-alkoxy, or C1-C2- alkylsu Ifanyl; R7is hydrogen or Ci-Cs-alkyl; and Z1is defined as for compounds of formula (I).

[0081] In another embodiment of the invention, a compound of formula (I), wherein B1is CR4; B2is N; R1, R2are R3are hydrogen; R4is hydrogen, halogen, cyano, Ci-Cs-alkyl, Ci-Cs-alkoxy, Ci-C2-alkoxycarbonyl, or C3-C4- cycloalkyl; Q is selected from Q6, Q7, Q8, Q9, Q10, Q11 , or Q14, wherein the staggered line denotes the attachment point of the Q substituent to the rest of the molecule; R6a, R6b, R6cand R6dare independently selected from hydrogen, halogen, Ci-Cs-alkyl, Ci-Cs-alkoxy, or Ci-C2-alkylsulfanyl; R7is hydrogen or C1-C3- alkyl; and Z1is defined as for compounds of formula (I).

[0082] In another embodiment of the invention, a compound of formula (I), wherein B1is CR4; B2is N; R1, R2are R3are hydrogen; R4is hydrogen, halogen, cyano, Ci-Cs-alkyl, Ci-Cs-alkoxy, Ci-C2-alkoxycarbonyl, or C3-C4- cycloalkyl; Q is selected from Q6, Q7, Q8, Q9, Q10, Q11 , or Q14, wherein the staggered line denotes the attachment point of the Q substituent to the rest of the molecule; R6a, R6b, R6cand R6dare independently selected from hydrogen, halogen, Ci-Cs-alkyl, Ci-Cs-alkoxy, or Ci-C2-alkylsulfanyl; R7is hydrogen or C1-C3- alkyl; and Z1is defined as for compounds of formula (I).

[0083] In another embodiment of the invention, a compound of formula (I), wherein B1is CR4; B2is N; R1, R2are R3are hydrogen; R4is hydrogen, halogen, cyano, Ci-Cs-alkyl, Ci-Cs-alkoxy, Ci-C2-alkoxycarbonyl, or C3-C4- cycloalkyl; Q is selected from Q6, Q7, Q8, Q9, Q10, Q11 , or Q14, wherein the staggered line denotes the attachment point of the Q substituent to the rest of the molecule; R6a, R6b, R6cand R6dare independently selected from hydrogen, halogen, Ci-Cs-alkyl, Ci-Cs-alkoxy, or Ci-C2-alkylsulfanyl; R7is hydrogen or C1-C3- alkyl; and Z1is selected from Ci-Ce-alkyl, wherein said Ci-Ce-alkyl is unsubstituted or substituted with 1 , 2 or 3 substituents independently selected from halogen, cyano, Ci-C4-alkyl, Ci-C2-alkoxy, Ci-C2-haloalkoxy, C2-C3- alkenyl, C2-C3-alkynyl, C2-C3-alkenyloxy, C2-C3-alkynyloxy, Ci-C2-alkylsulfanyl, Ci-C2-alkylsulfonyl, or cyclopropyl; and wherein said cyclopropyl is unsubstituted or substituted with 1 substituent selected from halogen, cyano, Ci-Cs-alkyl, or Ci-C2-haloalkyl.

[0084] In another embodiment of the invention, a compound of formula (I), wherein B1is CR4; B2is N; R1, R2are R3are hydrogen; R4is hydrogen, halogen, cyano, Ci-Cs-alkyl, Ci-Cs-alkoxy, Ci-C2-alkoxycarbonyl, or C3-C4- cycloalkyl; Q is selected from Q6, Q7, Q8, Q9, Q10, Q11 , or Q14, wherein the staggered line denotes the attachment point of the Q substituent to the rest of the molecule; R6a, R6b, R6cand R6dare independently selected from hydrogen, halogen, Ci-Cs-alkyl, Ci-Cs-alkoxy, or Ci-C2-alkylsulfanyl; R7is hydrogen or C1-C3- alkyl; and Z1is selected from Ci-Cs-alkyl, wherein said Ci-Cs-alkyl is unsubstituted or substituted with 1 , 2 or 3 substituents independently selected from halogen, cyano, Ci-C4-alkyl, Ci-C2-alkoxy, Ci-C2-haloalkoxy, C2-C3- alkenyl, C2-C3-alkynyl, C2-C3-alkenyloxy, C2-C3-alkynyloxy, Ci-C2-alkylsulfanyl, Ci-C2-alkylsulfonyl, or cyclopropyl.

[0085] In one embodiment of the invention, a compound of formula (I), wherein B1is CR4; B2is N; and wherein R1, R2, R3, R4, R6(R6a, R6b, R6cand R6d), R7, Q and Z1are defined as for compounds of formula (I).

[0086] In another embodiment of the invention, a compound of formula (I), wherein B1is N; B2is CR5; R1and R2are hydrogen; R3is hydrogen, halogen, cyano, Ci-Cs-alkyl, or Cs-Cs-cycloalkyl; and R5, R6(R6a, R6b, R6cand R6d), R7, Q and Z1are defined as for compounds of formula (I).

[0087] In another embodiment of the invention, a compound of formula (I), wherein B1is N; B2is CR5;; R1, R2are R3are hydrogen; and R5, R6(R6a, R6b, R6cand R6d), R7, Q and Z1are defined as for compounds of formula (I).

[0088] In another embodiment of the invention, a compound of formula (I), wherein B1is N; B2is CR5; R1, R2are R3are hydrogen; R5is hydrogen, halogen, cyano, Ci-Cs-alkyl, Ci-Cs-alkoxy, Ci-C2-alkoxycarbonyl, or C3-C4- cycloalkyl; and R6(R6a, R6b, R6cand R6d), R7, Q and Z1are defined as for compounds of formula (I).

[0089] In another embodiment of the invention, a compound of formula (I), wherein B1is N; B2is CR5; R1, R2are R3are hydrogen; R5is hydrogen, halogen, cyano, Ci-Cs-alkyl, Ci-Cs-alkoxy, Ci-C2-alkoxycarbonyl, or C3-C4- cycloalkyl; R6a, R6b, R6cand R6dare independently selected from hydrogen, halogen, Ci-Cs-alkyl, Ci-Cs-alkoxy, or Ci-C2-alkylsulfanyl; R7is hydrogen or Ci-Cs-alkyl; and wherein Q and Z1are defined as for compounds of formula (I).

[0090] In another embodiment of the invention, a compound of formula (I), wherein B1is N; B2is CR5; R1, R2are R3are hydrogen; R5is hydrogen, halogen, cyano, Ci-Cs-alkyl, Ci-Cs-alkoxy, Ci-C2-alkoxycarbonyl, or C3-C4- cycloalkyl; R6a, R6b, R6cand R6dare independently selected from hydrogen, halogen, Ci-Cs-alkyl, Ci-Cs-alkoxy, or Ci-C2-alkylsulfanyl; R7is hydrogen or Ci-Cs-alkyl; and Q and Z1are defined as for compounds of formula (I). In another embodiment of the invention, a compound of formula (I), wherein B1is N; B2is CR5; R1, R2are R3are hydrogen; R5is hydrogen, halogen, cyano, Ci-Cs-alkyl, Ci-Cs-alkoxy, Ci-C2-alkoxycarbonyl, or C3-C4- cycloalkyl; Q is selected from Q1 , Q2, Q4, Q6, Q7, Q8, Q9, Q11 , Q12, Q13, Q16, Q17, Q18, Q20, Q21 or Q22 as defined above; wherein the staggered line denotes the attachment point of the Q substituent to the rest of the molecule; R6a, R6b, R6cand R6dare independently selected from hydrogen, halogen, Ci-Cs-alkyl, C1-C3- alkoxy, or Ci-C2-alkylsulfanyl; R7is hydrogen or Ci-Cs-alkyl; and Z1is defined as for compounds of formula (I).

[0091] In another embodiment of the invention, a compound of formula (I), wherein B1is N; B2is CR5; R1, R2are R3are hydrogen; R5is hydrogen, halogen, cyano, Ci-Cs-alkyl, Ci-Cs-alkoxy, Ci-C2-alkoxycarbonyl, or C3-C4- cycloalkyl; Q is selected from Q6, Q7, Q8, Q9, Q10, Q11 , or Q14, wherein the staggered line denotes the attachment point of the Q substituent to the rest of the molecule; R6a, R6b, R6cand R6dare independently selected from hydrogen, halogen, Ci-Cs-alkyl, Ci-Cs-alkoxy, or Ci-C2-alkylsulfanyl; R7is hydrogen or C1-C3- alkyl; and Z1is defined as for compounds of formula (I).

[0092] In another embodiment of the invention, a compound of formula (I), wherein B1is N; B2is CR5; R1, R2are R3are hydrogen; R5is hydrogen, halogen, cyano, Ci-Cs-alkyl, Ci-Cs-alkoxy, Ci-C2-alkoxycarbonyl, or C3-C4- cycloalkyl; Q is selected from Q6, Q7, Q8, Q9, Q10, Q11 , or Q14, wherein the staggered line denotes the attachment point of the Q substituent to the rest of the molecule; R6a, R6b, R6cand R6dare independently selected from hydrogen, halogen, Ci-Cs-alkyl, Ci-Cs-alkoxy, or Ci-C2-alkylsulfanyl; R7is hydrogen or C1-C3- alkyl; and Z1is defined as for compounds of formula (I).

[0093] In another embodiment of the invention, a compound of formula (I), wherein B1is N; B2is CR5; R1, R2are R3are hydrogen; R5is hydrogen, halogen, cyano, Ci-Cs-alkyl, Ci-Cs-alkoxy, Ci-C2-alkoxycarbonyl, or C3-C4- cycloalkyl; Q is selected from Q6, Q7, Q8, Q9, Q10, Q11 , or Q14, wherein the staggered line denotes the attachment point of the Q substituent to the rest of the molecule; R6a, R6b, R6cand R6dare independently selected from hydrogen, halogen, Ci-Cs-alkyl, Ci-Cs-alkoxy, or Ci-C2-alkylsulfanyl; R7is hydrogen or C1-C3- alkyl; and Z1is selected from Ci-Cs-alkyl, wherein said Ci-Cs-alkyl is unsubstituted or substituted with 1 , 2 or 3 substituents independently selected from halogen, cyano, Ci-C4-alkyl, Ci-C2-alkoxy, Ci-C2-haloalkoxy, C2-C3- alkenyl, C2-C3-alkynyl, C2-C3-alkenyloxy, C2-C3-alkynyloxy, Ci-C2-alkylsulfanyl, Ci-C2-alkylsulfonyl, or cyclopropyl; and wherein said cyclopropyl is unsubstituted or substituted with 1 substituent selected from halogen, cyano, Ci-Cs-alkyl, or Ci-C2-haloalkyl.

[0094] In another embodiment of the invention, a compound of formula (I), wherein B1is N; B2is CR5; R1, R2are R3are hydrogen; R5is hydrogen, halogen, cyano, Ci-Cs-alkyl, Ci-Cs-alkoxy, Ci-C2-alkoxycarbonyl, or C3-C4- cycloalkyl; Q is selected from Q6, Q7, Q8, Q9, Q10, Q11 , or Q14, wherein the staggered line denotes the attachment point of the Q substituent to the rest of the molecule; R6a, R6b, R6cand R6dare independently selected from hydrogen, halogen, Ci-Cs-alkyl, Ci-Cs-alkoxy, or Ci-C2-alkylsulfanyl; R7is hydrogen or C1-C3- alkyl; and Z1is selected from Ci-Cs-alkyl, wherein said Ci-Cs-alkyl is unsubstituted or substituted with 1 , 2 or 3 substituents independently selected from halogen, cyano, Ci-C4-alkyl, Ci-C2-alkoxy, Ci-C2-haloalkoxy, C2-C3- alkenyl, C2-C3-alkynyl, C2-C3-alkenyloxy, C2-C3-alkynyloxy, Ci-C2-alkylsulfanyl, Ci-C2-alkylsulfonyl, or cyclopropyl. In one embodiment of the invention, a compound of formula (I), wherein B1is CR4; B2is CR5; and wherein R1, R2, R3, R4, R5, R6(R6a, R6b, R6cand R6d), R7, Q and Z1are defined as for compounds of formula (I).

[0095] In another embodiment of the invention, a compound of formula (I), wherein B1is CR4; B2is CR5; R1and R2are hydrogen; R3is hydrogen, halogen, cyano, Ci-Cs-alkyl, or Cs-Ce-cycloalkyl; and R4, R5, R6(R6a, R6b, R6cand R6d), R7, Q and Z1are defined as for compounds of formula (I).

[0096] In another embodiment of the invention, a compound of formula (I), wherein B1is CR4; B2is CR5; R1, R2are R3are hydrogen; and R4, R5, R6(R6a, R6b, R6cand R6d), R7, Q and Z1are defined as for compounds of formula (I).

[0097] In another embodiment of the invention, a compound of formula (I), wherein B1is CR4; B2is CR5; R1, R2are R3are hydrogen; R4and R5are independently selected from hydrogen, halogen, cyano, Ci-Cs-alkyl, Ci-Cs-alkoxy, Ci-C2-alkoxycarbonyl, or C3-C4-cycloalkyl; and R6(R6a, R6b, R6cand R6d), R7, Q and Z1are defined as for compounds of formula (I).

[0098] In another embodiment of the invention, a compound of formula (I), wherein B1is CR4; B2is CR5; R1, R2are R3are hydrogen; R4and R5are independently selected from hydrogen, halogen, cyano, Ci-Cs-alkyl, Ci-Cs-alkoxy, Ci-C2-alkoxycarbonyl, or C3-C4-cycloalkyl; R6a, R6b, R6cand R6dare independently selected from hydrogen, halogen, Ci-Cs-alkyl, Ci-Cs-alkoxy, or Ci-C2-alkylsulfanyl; R7is hydrogen or Ci-Cs-alkyl; and Q and Z1are defined as for compounds of formula (I).

[0099] In another embodiment of the invention, a compound of formula (I), wherein B1is CR4; B2is CR5; R1, R2are R3are hydrogen; R4and R5are independently selected from hydrogen, halogen, cyano, Ci-Cs-alkyl, Ci-Cs-alkoxy, Ci-C2-alkoxycarbonyl, or C3-C4-cycloalkyl; R6a, R6b, R6cand R6dare independently selected from hydrogen, halogen, Ci-Cs-alkyl, Ci-Cs-alkoxy, or Ci-C2-alkylsulfanyl; R7is hydrogen or Ci-Cs-alkyl; and Q and Z1are defined as for compounds of formula (I).

[0100] In another embodiment of the invention, a compound of formula (I), wherein B1is CR4; B2is CR5; R1, R2are R3are hydrogen; R4and R5are independently selected from hydrogen, halogen, cyano, Ci-Cs-alkyl, Ci-Cs-alkoxy, Ci-C2-alkoxycarbonyl, or C3-C4-cycloalkyl; Q is selected from Q1 , Q2, Q4, Q6, Q7, Q8, Q9, Q11 , Q12, Q13, Q16, Q17, Q18, Q20, Q21 or Q22 as defined above; wherein the staggered line denotes the attachment point of the Q substituent to the rest of the molecule; R6a, R6b, R6cand R6dare independently selected from hydrogen, halogen, Ci-Cs-alkyl, Ci-Cs-alkoxy, or Ci-C2-alkylsulfanyl; R7is hydrogen or Ci-Cs-alkyl; and Z1is defined as for compounds of formula (I).

[0101] In another embodiment of the invention, a compound of formula (I), wherein B1is CR4; B2is CR5; R1, R2are R3are hydrogen; R4and R5are independently selected from hydrogen, halogen, cyano, Ci-Cs-alkyl, Ci-Cs-alkoxy, Ci-C2-alkoxycarbonyl, or C3-C4-cycloalkyl; Q is selected from Q6, Q7, Q8, Q9, Q10, Q11 , or Q14, wherein the staggered line denotes the attachment point of the Q substituent to the rest of the molecule; R6a, R6b, R6cand R6dare independently selected from hydrogen, halogen, Ci-Cs-alkyl, Ci-Cs-alkoxy, or Ci-C2-alkylsulfanyl; R7is hydrogen or Ci-Cs-alkyl; and Z1is defined as for compounds of formula (I).

[0102] In another embodiment of the invention, a compound of formula (I), wherein B1is CR4; B2is CR5; R1, R2are R3are hydrogen; R4and R5are independently selected from hydrogen, halogen, cyano, Ci-Cs-alkyl, Ci-Cs-alkoxy, Ci-C2-alkoxycarbonyl, or C3-C4-cycloalkyl; Q is selected from Q6, Q7, Q8, Q9, Q10, Q11 , or Q14, wherein the staggered line denotes the attachment point of the Q substituent to the rest of the molecule; R6a, R6b, R6cand R6dare independently selected from hydrogen, halogen, Ci-Cs-alkyl, Ci-Cs-alkoxy, or Ci-C2-alkylsulfanyl; R7is hydrogen or Ci-Cs-alkyl; and Z1is defined as for compounds of formula (I).

[0103] In another embodiment of the invention, a compound of formula (I), wherein B1is CR4; B2is CR5; R1, R2are R3are hydrogen; R4and R5are independently selected from hydrogen, halogen, cyano, Ci-Cs-alkyl, Ci-Cs-alkoxy, Ci-C2-alkoxycarbonyl, or C3-C4-cycloalkyl; Q is selected from Q6, Q7, Q8, Q9, Q10, Q11 , or Q14, wherein the staggered line denotes the attachment point of the Q substituent to the rest of the molecule; R6a, R6b, R6cand R6dare independently selected from hydrogen, halogen, Ci-Cs-alkyl, Ci-Cs-alkoxy, or Ci-C2-alkylsulfanyl; R7is hydrogen or Ci-Cs-alkyl; and Z1is selected from Ci-Cs-alkyl, wherein said Ci-Cs-alkyl is unsubstituted or substituted with 1 , 2 or 3 substituents independently selected from halogen, cyano, Ci-C4-alkyl, Ci-C2-alkoxy, Ci-C2-haloalkoxy, C2-C3-alkenyl, C2-C3-alkynyl, C2-C3-alkenyloxy, C2-C3-alkynyloxy, Ci-C2-alkylsulfanyl, C1-C2- alkylsulfonyl, or cyclopropyl; and wherein said cyclopropyl is unsubstituted or substituted with 1 substituent selected from halogen, cyano, Ci-Cs-alkyl, or Ci-C2-haloalkyl.

[0104] In another embodiment of the invention, a compound of formula (I), wherein B1is CR4; B2is CR5; R1, R2are R3are hydrogen; R4and R5are independently selected from hydrogen, halogen, cyano, Ci-Cs-alkyl, Ci-Cs-alkoxy, Ci-C2-alkoxycarbonyl, or C3-C4-cycloalkyl; Q is selected from Q6, Q7, Q8, Q9, Q10, Q11 , or Q14, wherein the staggered line denotes the attachment point of the Q substituent to the rest of the molecule; R6a, R6b, R6cand R6dare independently selected from hydrogen, halogen, Ci-Cs-alkyl, Ci-Cs-alkoxy, or Ci-C2-alkylsulfanyl; R7is hydrogen or Ci-Cs-alkyl; and Z1is selected from Ci-Cs-alkyl, wherein said Ci-Cs-alkyl is unsubstituted or substituted with 1 , 2 or 3 substituents independently selected from halogen, cyano, Ci-C4-alkyl, Ci-C2-alkoxy, Ci-C2-haloalkoxy, C2-C3-alkenyl, C2-C3-alkynyl, C2-C3-alkenyloxy, C2-C3-alkynyloxy, Ci-C2-alkylsulfanyl, C1-C2- alkylsulfonyl, or cyclopropyl.

[0105] The presence of one or more possible asymmetric carbon atoms in any of the compounds selected from compounds of formula (I), or compounds selected from compounds listed in Tables C-1 to C-56, or compounds listed in Table P (below), according to the invention means that the compounds may occur in chiral isomeric forms, i.e., enantiomeric or diastereomeric forms.

[0106] In one embodiment, the compound of formula (I) according to the invention is selected from compounds listed in any one of Tables C-1 to C-56.

[0107] In another embodiment, the compound of formula (I) according to the invention is selected from compounds as listed in Table P (below).

[0108] In a preferred embodiment, the compound of formula (I) according to the invention is selected from 4-(4,5- dimethylpyrazol-1-yl)-N-pentyl-quinoline-2-carboxamide (P-1 ), 4-(4,5-dimethyltriazol-1-yl)-N-pentyl-quinoline- 2-carboxamide (P-2), 4-(4,5-dimethylimidazol-1-yl)-N-pentyl-quinoline-2-carboxamide (P-3), 4-(2,3- dimethylimidazol-4-yl)-N-pentyl-quinoline-2-carboxamide (P-4), 4-(1 ,5-dimethylimidazol-2-yl)-N-pentyl- quinoline-2-carboxamide (P-5), 4-(5-chloro-1 ,2-dimethyl-imidazol-4-yl)-N-pentyl-quinoline-2-carboxamide (P- 6), N-(3-cyclopropylpropyl)-4-(2,5-dichloro-1-methyl-imidazol-4-yl)quinoline-2-carboxamide (P-7), 4-(2,5- dichloro-1-methyl-imidazol-4-yl)-N-pentyl-quinoline-2-carboxamide (P-8), 4-(5-chloro-1-methyl-imidazol-4-yl)- N-pentyl-quinoline-2-carboxamide (P-9), 4-(2-chloro-1 ,5-dimethyl-imidazol-4-yl)-N-(3- cyclopropylpropyl)quinoline-2-carboxamide (P-10), 4-(2-chloro-1 ,5-dimethyl-imidazol-4-yl)-N-pentyl-quinoline- 2-carboxamide (P-11 ), 4-(1 ,5-dimethylimidazol-4-yl)-N-pentyl-quinoline-2-carboxamide (P-12), N-(3- cyclopropylpropyl)-4-(1 ,5-dimethyltriazol-4-yl)quinoline-2-carboxamide (P-13), 4-(1 ,5-dimethyltriazol-4-yl)-N- pentyl-quinoline-2-carboxamide (P-14), N-pentyl-4-(3,4,5-trimethylpyrazol-1-yl)quinoline-2-carboxamide (P- 15), 4-(3,5-dimethylpyrazol-1-yl)-N-pentyl-quinoline-2-carboxamide (P-16), 4-(2-methylimidazol-1-yl)-N-pentyl- quinoline-2-carboxamide (P-17), 4-(5-chloro-1-methyl-triazol-4-yl)-N-pentyl-quinoline-2-carboxamide (P-18), 4- (5-chloro-1-methyl-triazol-4-yl)-N-(3-cyclopropylpropyl)quinoline-2-carboxamide (P-19), 4-(3-methylpyrazol-1- yl)-N-pentyl-quinoline-2-carboxamide (P-20), or 4-(3,4-dimethylpyrazol-1-yl)-N-pentyl-quinoline-2- carboxamide (P-21 ).

[0109] The compounds of formula (I) according to the present invention can be made as shown in the following Schemes 1 to 18, in which, unless otherwise stated, the definition of each variable is as defined above for a compound of formula (I).

[0110] In particular, compounds of formula (I), wherein R1, R2, R3, B1, B2, Q, and Z1are as described under formula (I) in can be prepared as described in Schemes 1 to 18, in which, unless otherwise stated, the definition of each variable is as defined above for a compound of formula (I).

[0111] In any of the Schemes 1 to 18 below, the presence of one or more possible asymmetric carbon atoms in a compound of formula (I) according to the invention means that the compounds may occur in chiral isomeric forms, i.e., enantiomeric or diastereomeric forms.

[0112] Compounds of formula (I) may be prepared by a person skilled in the art following known methods. More specifically, compounds of formula (I) may be prepared from compounds of formula (III) or a salt thereof, wherein Z1as defined above for the compound of formula (I) by reaction with a compound of formula (II), wherein R1, R2, R3, Q, B1, and B2are as defined above for the compound of formula (I) (Scheme 1 ).

[0113]

[0114] Scheme 1

[0115] In Scheme 1 , compounds of formula (II), wherein R1, R2, R3, B1, and B2are as defined above for the compound of formula (I), are activated to compounds of formula (Ila) by methods known to a person skilled in the art and described, for example, in Tetrahedron 2005, 61 (46), 10827-10852. For example, compounds of formula (Ila), where X° is halogen, are formed by treatment of compounds of formula (II) with, for example, oxalyl chloride or thionyl chloride in the presence of catalytic quantities of N,N-dimethylformamide (DMF) in inert solvents, such as dichloromethane (DCM) or tetrahydrofuran (THF), at temperatures between 0°C to 100°C, preferably 25°C. Treatment of compounds of formula (Ila) with compounds of formula (III), wherein Z1is as defined above for the compound of formula (I), optionally in the presence of a base, e.g. triethylamine or pyridine, leads to compounds of formula (I). Alternatively, compounds of formula (I) may be prepared by treatment of compounds of formula (II) with dicyclohexyl carbodiimide (DCC), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) or 1-[bis(dimethylamino)methylene]-1 H-1 ,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU) to give the activated compound of formula (lib), wherein G° is G01, G02or G03as set forth below, in an inert solvent, e.g. pyridine, DMF, acetonitrile, DCM, or THF, optionally in the presence of a base, e.g. triethylamine, at temperatures between 0°C and 180°C. Finally, a compound of formula (II) can also be activated by reaction with a coupling reagent such as propanephosphonic acid anhydride (T3P) to provide compounds of formula (Ila), wherein G° is G04as set forth below, as described for example in Synthesis 2013, 45, 1569. Further reaction with an amine (or a salt thereof) of the compound of formula (III) leads to compounds of formula (I).

[0116] Compounds of formula (II) can be prepared from compounds of formula (He), wherein R1, R2, R3, Q, B1, and B2are as described in formula (I), and R01is Ci-C4-alkyl, by ester hydrolysis. A variety of conditions can be used, as for example aqueous sodium hydroxide or lithium hydroxide and an organic water miscible solvent like THF, dimethoxyethane, methanol, or ethanol. Such ester hydrolyses are well known to those skilled in the art. Compounds of formula (lie) can also be directly converted to compounds of formula (I) by reacting compounds of formula (lie) with compounds of formula (III) in the presence of trimethyl aluminum, or trimethyl aluminum- DABCO complex in an inert solvent such as toluene or methylene chloride. Such reactions have been reported in the literature (see Tetrahedron Lett. 1977, 4171 -4174, and Tetrahedron Lett. 2006, 5767-5769, and references cited therein). A further method to prepare compounds of formula (I) involves amino carbonylation of compounds of formula (III) with compounds of formula (IV), wherein R1, R2, R3, Q, B1, and B2, are as defined in compounds of formula (I), and X° is halogen, preferably Cl, Br, or I. Such amino carbonylation’s involve treatment of compounds of formula (III) with compounds of formula (IV) under a carbon monoxide atmosphere between 1 and 10 bar, in the presence of a palladium catalyst, for example [1 ,3- Bis(diphenylphosphino)propane] palladium^ I) chloride in an inert solvent, such as methyl-THF or THF, and a base, such as triethylamine. Such amino carbonylation reactions are well known to those skilled in the art and similar reactions have been reported in Org. Lett. 2007, 9, 4575-4578, or Org. Lett. 2015, 17, 3236-3239.

[0117] Compounds of formula (He), wherein R1, R2, R3, Q, B1and B2are as defined above for the compound of formula (I), and R01is Ci-C4-alkyl, may be prepared by reacting compounds of formula (IV) wherein R1, R2, R3, Q, B1, B2are as defined above for the compound of formula (I), and X° is halogen, in a high-pressure reactor typically under a carbon monoxide between 1-10 bar using palladium-catalyzed conditions analogously to conditions described in US2015 / 0218102 or WO1998 / 04557. This reaction is carried out in the presence of an alcohol R01-OH wherein R01is Ci-C4-alkyl, and a base, for example triethylamine, to give the corresponding ester where R01is Ci-C4-alkyl (Scheme 2).

[0118] Scheme 2 Compounds of formula (IV), wherein R1, R2, R3, B1and B2are as defined above, and X° is halogen, preferably Cl, namely compounds of formula (IVa), may be prepared by reacting compounds of formula (V), wherein and R1, R2, R3, Q, B1and B2are as defined above for the compound of formula (I), with a chlorinating agent such as phosphorus oxychloride, oxalyl chloride or thionyl chloride neat, or in a an inert solvent such as DCM. Similar reactions have been described for example in Tetrahedron Lett. 2014, 55(51 ), 7130-7132 (Scheme 3).

[0119] Scheme 3

[0120] Compounds of formula (V), wherein R1, R2, R3, Q, B1and B2are as defined above for the compound of formula (I), may be prepared by reacting compounds of formula (VI), wherein R1, R2, R3, Q, B1and B2are as defined above for compounds of formula (I), with an oxidizing agent, such as hydrogen peroxide, in acetic acid or m- chloroperbenzoic acid, in the presence of a solvent. Similar reactions have been described in W004 / 052370 or / tdv. Synth. Cat. 2020, 362(24), 5777-5782. Such oxidations can also be performed in presence of oxygen using a ruthenium salt as catalyst as described in Chem. Comm. 2002, (10), 1040-1041 (Scheme 4).

[0121] Scheme 4

[0122] Compounds of formula (VI) may be prepared by reacting organometallic compounds of formula (VII), wherein R1, R2, R3, B1and B2are as defined above for compounds of formula (I), and M01is B(OH)2, (4,4,5,5-tetramethyl- 1 ,3,2-dioxaborolan-2-yl), or ZnX°, wherein X° is halogen, with a compound of formula (VIII), wherein X° is halogen, preferably Cl, Br, or I; and Q is Q1 , Q2, Q4, Q5, Q7, Q8, Q9, Q1 1 , Q12, Q13, Q16, Q17, Q18, Q20 or Q21 , by means of a C-C bond formation reaction under palladium or nickel-catalyzed cross-coupling conditions (Scheme 5).

[0123] Scheme 5 Reactions between compounds of formula (VII) wherein M01is B(OH)2, (4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan- 2-yl), and compounds of formula (VIII), are known by those skilled in the art as Suzuki-Miyaura cross-coupling reactions. They are usually carried out in the presence of a palladium catalyst, such as tetrakis(triphenylphosphine)-palladlum(0) or [1 ,T-bis(diphenylphosphino)ferrocene]palladium(ll) dichloride dichloromethane complex, and a base, such as sodium or potassium carbonate, in a solvent, such as DMF, dioxane, or dioxane-water mixtures, at temperatures between room temperature and 160°C, optionally under microwave heating conditions, and preferably under an inert atmosphere. Such reactions have been reviewed for example in J. Organomet. Chem. 1999, 576, 147-168. Alternatively, reaction between compounds (VII), wherein M01Is ZnX° and X° is halogen, preferably Cl, Br, or I, and compounds of formula (VIII), known to those skilled in the art as Negishi coupling reactions, can be used to prepare compounds of formula (VI). The reactions are also traditionally catalyzed by palladium species similar to those involved in Suzuki-Miyaura cross-coupling reactions. Such conditions are described in for example Org. Let. 2008, 10, 4705-4707 or J. Org. Chem. 2010, 75, 8330-8332, and references cited therein. Both Suzuki-Miyaura and Negishi cross coupling reactions are also well established with Ni-catalysts as described for example in Organometallics 2022, 41, 11 , 1269-1274, and Org. Let. 2011 , 13, 1218-1221. Compounds of formula (VII) are readily prepared from compounds of formula (IX) by many chemical transformations, well known by those skilled in the art (Scheme 6).

[0124] Scheme 6

[0125] As show in scheme 6, organometalic intermediate of the formula (VII) can be prepared from compounds of formula (IX) wherein X° is chlorine, bromine, or iodine, via metal-halogen exchange with an organometallic species such as butyl lithium or an organo magnesium compound (e.g. Turbo Grignard), or via direct metalation with a metal, like magnesium or zinc, yielding compounds of formulae (VI I b), (Vile) or (VI Id). Introduction of a pinacolborate functional group via a palladium catalyzed reaction with bispinacol diborane, in compounds of formula (IX), wherein X° is chlorine, bromine, or iodine, is another common strategy to prepare compounds of formula (Vila). A further cross-coupling reaction, namely C-H activation, can also be used to prepare compounds of formula (VI), wherein R1, R2, R3, B1, and B2are as defined above for the compound of formula (I), and Q is Q1 , Q2, Q4, Q5, Q7, Q8, Q9, Q11 , Q12, Q13, Q16, Q17, Q18, Q20, or Q21 as defined above (Scheme 7).

[0126] Scheme 7

[0127] As shown in Scheme 7, compounds of formula (IX), wherein R1, R2, R3, B1and B2are as defined above for the compound of formula (I), and X° is halogen, preferably chlorine, bromine or iodine, are reacted with compounds of formula (X), in the presence of a palladium catalyst, typically palladium acetate Pd(OAc)2, a suitable ligand, for example 1 ,10-phenanthroline, in the presence of a base such as cesium carbonate or potassium carbonate, in inert solvents such as chlorobenzene, toluene, or xylene, at temperatures between room temperature and 180°C, optionally under microwave heating conditions, preferably under an inert atmosphere. Similar reactions have been reported in the literature, for example in Chem. Sci. 2013, 4, 2374-2379. Compounds of formula (IX) are commercially available or prepared by methods known to those skilled in the art.

[0128] A person skilled in the art will immediately recognize that the C-C coupling reactions described above can be performed in the reverse manner, namely by reacting a compound of formula (IX), wherein R1, R2R3, B1and B2are as defined above for the compound of formula (I), and X° is halogen, with a compound of formula (XI), wherein M° is a metalated species as described vide infra, and wherein and Q is Q1 , Q2, Q4, Q5, Q7, Q8, Q9, Q11 , Q12, Q13, Q16, Q17, Q18, Q20, or Q21 as defined above (Scheme 8).

[0129] Scheme 8

[0130] Those highly skilled in the art will recognize that proto deborylation can be an issue in reactions where boronic acids, or esters thereof, are adjacent to nitrogen in compounds of formula (XI). Solutions to this problem are available on a case to case basis, as described in, for example Dyes Pigment. 2023, 209, Part B, pp 110899 and Isr. J. Chem. 2010, 50, 664.

[0131] Compounds of formula (I), wherein R1, R2, R3, Q, B1, B2and Z1are as described in formula (I), can also be prepared as shown in schemes 9 to 20.

[0132]

[0133] As shown in scheme 9, compounds of formula (XII) upon reaction with compounds of formula (XIII), wherein R01is Ci-C4-alkyl, in an organic solvent such as methanol, toluene, THF and the like, lead to compounds of formula (XIV). Compounds of formula (XIV) can be cyclized to compounds of formula (XV) by, for example, heating at temperatures between 200 and 250°C neat, or in an organic solvent such as diphenyl ether or 1 ,2- dichlorbenzene. Such reactions have been described for example in Dalton Trans. 2012, 41 (31 ), 9373-9381 , and Molecules 2019, 24(19), 3502. Compounds of formula (XV) can be converted to compounds of formula (XVI), wherein R2, R3, B1, B2, are defined as for compounds of formula (I), and R01is Ci-C4-alkyl, and X° is halogen, by halogenation with for example P=OX°3 (e.g. phosphoryl chloride or phosphoryl bromide), under conditions know to those skilled in the art and described, for example, in Bio. Med. Chem. Lett. 2010, 20(3), 954-957, and J. Med. Chem. 2006, 49(21 ), 6351 -6363. Compounds of formula (XVI) can be then converted to boronic acids, boronic esters, organozinc compounds to under conditions analogous to those described in scheme 6 to give compounds of formula (XVII), and (XVI la) (XVIIb) and (XVIIc). Compounds of formula (XVII) can then be converted to compounds of formula (He) using Suzuki- Miyaura and Negishi coupling conditions with compounds of formula (VIII), by reaction with Q-X°, wherein X° is halogen, preferably Cl, Br, or I; and Q is Q1 , Q2, Q4, Q5, Q7, Q8, Q9, Q11 , Q12, Q13, Q16, Q17, Q18, Q20 or Q21 ; as defined above, analogous to the methods described under scheme 5 (Scheme 10). Compounds of formula (lie) are converted to compounds of formula (I) as described in Scheme 1.

[0134]

[0135] Scheme 10

[0136] As shown in scheme 10, compounds of formula (XVI) upon metalation give compounds of formula (XVII) and ultimately (XVIIa), (XVIIb) and (XVIIc). Upon reaction with Q-X° (VIII) compounds of formula (lie) are obtained. Compounds of formula (He) can also be obtained similarly from (XVI) by Suzuki-Miyaura and Negishi couplings (Scheme 11 ) with compounds of formula (XI), wherein Q is Q1 , Q2, Q4, Q5, Q7, Q8, Q9, Q11 , Q12, Q13, Q16, Q17, Q18, Q20 or Q21 are as defined above. A further method to prepare compounds of formula (lie) involves reactions of compounds of formula (XVI) with compounds of formula (X), wherein Q-H is as defined in scheme 7, using C-H activation conditions described under scheme 7. Transformation of compounds of (lie) using the methods described in Scheme 1 leads to compounds of formula (la), wherein R2, R3, B1, B2, and Z1are defined as for compounds of formula (I), and Q is Q1 , Q2 Q4, Q5, Q7, Q8, Q9, Q11 , Q12, Q13, Q15, Q16, Q17, Q18, Q20, Q21 , or Q22. This is shown in scheme 12.

[0137] Scheme 12

[0138] In the particular case where compounds of formula (I) have the group Q attached through a nitrogen atom (e.g. Q is a 5-membered heteroaromatic ring containing an NH functionality), namely compounds of formula (Xa), wherein Q is Q3, Q6, Q10, Q14, Q15, Q19, or Q22.

[0139] Compounds of formula (Ila) can be accessed by reacting compounds of formula (XVI) with a compounds of formula (Xa) in the presence of a base, such as potassium carbonate or cesium carbonate, optionally in the presence of a copper catalyst, for example copper(l)iodide, with or without an additive such as L-proline, N,N'- dimethylcyclohexane-1 ,2-diamine, or N,N’-dimethylethylene-diamine, in an inert solvent such as N- methylpyrrolidone, NMP, or DMF, at temperatures between 0 and 150°C, optionally under microwave irradiation, such reactions are known in the literature, for example Catalysts 2022, 72(8), 911. (Scheme 13).

[0140] Scheme 13

[0141] Compounds of formula (Ila) are converted to compounds of formula (I), as described in scheme 1.

[0142] A further method of preparing compounds of formula (Ila) involves reaction of compounds of formula (Xa) with compounds of formula (XVIIa) or (XVIIb) using Chan-Lamm conditions. Chan-Lamm reactions allow carbonnitrogen bond formations between boronic acids (or esters thereof) and compounds of formula (Xa), wherein Q is Q3, Q6, Q10, Q14, Q15, Q19, or Q22 as defined above, containing an N-H functionality under copper catalyzed conditions. When applied in this senario, compounds of formula (XVIIa) or (lib) with compounds of formula (Xa) yield compounds of formula (Ila), wherein Q is an N-bound five membered heterocyclic ring, wherein R2, R3, B1, and B2are defined as for compounds of formula (I), and R01is Ci-C4-alkyl. Such Chan- Lamm reactions are well known in the literature, for example Adv. Synth. Catal. 2020, 362, 3311-3331 and references cited therein (Scheme 14).

[0143] (XVIIa) R02,R02= -C(CH3)2(CH3)2C-

[0144] (XVIIb) R02= H

[0145] Scheme 14

[0146] Methods to prepare compounds of formula (I) using de novo synthesis of the Q substituent are also possible from compounds of formula (XVI). For example, compounds of formula (He) wherein Q is Q11 , Q12, or Q13, namely compounds of formula (Ilea), (llcb), (llcc), and lied) formula can be prepared as shown scheme 15.

[0147] Scheme 15

[0148] As shown in scheme 15, Sonogashira reaction between compounds of formula (XVI) and compounds of formula (XVIII), wherein R6ais hydrogen, halogen, Ci-Cs-alkyl, Ci-Cs-alkoxy, or Ci-C2-alkylsulfanyl, using a suitable palladium catalyst, for example dichlorobis(triphenylphosphine)palladium, a copper catalyst, such as copper(l)iodide, and a base, such as triethylamine, optionally in the presence of a solvent, such as acetonitrile or DMF, lead to compounds of formula (XIX). Such Sonogashira reactions are well known to those skilled in the art and have been reviewed for example in Chem. Soc. Rev. 2011 , 40(10), 5084-512, and references cited therein. Sonogashira reactions are also known where R6ais bound to the terminal acetylene (XVIII) via a heteroatom (see WO2014 / 154486 and Bio. Med. Chem. Lett. 2008, 18(11 ), 3321-3327). Compounds of formula (XIX) can be treated with an alkaline earth metal azide, such as sodium azide, in a solvent, typically a dipolar aprotic solvent such as DMF, at temperatures from 60 to 120°C to yield the [3+2] cycloaddition product of formula (llcc), this type of Huisgen reaction has been described in Pure. Appl. Chem. 1989, 61 , 613-628. Compounds of formula (llcc) can be N-alkylated by reaction with compounds of formula (XXI), wherein R7is Ci-C4-alkyl, in an inert solvent such as DMF or acetonitrile, in the presence of a base such as sodium hydride or potassium carbonate, to give compounds of formula (Ilea), (llcb) and (lied). Compounds of formula (Ilea) can be obtained selectively by treatment of Ci-C4-alkylazides of formula (XX) by copper(l)salt-catalyzed azidealkyne cycloaddition. This reaction is usually carried out at room temperature with Cu(l) salts (or Cu(ll) salts) using sodium ascorbate as the reducing agent, see J. Am. Chem. Soc. 2005, 127, 210-216. Compounds of formula (Ilea), (llcb), (llcc), and (lied) are converted to compounds of formula (I) as previously described.

[0149] Compounds of formula (lie), wherein Q is Q20 or Q21 , namely compounds of formula (lice), (llcf), (llcg) and (llch), can be obtained as shown in Scheme 16.

[0150] (llcf) (llcg) (llch)

[0151] Scheme 16

[0152] As shown in Scheme 16, compounds of formula (XVI) are easily converted to compounds of formula (XXII) by cyanation reactions with cyanide salts of formula M02CN, wherein M02is a metal, such as iron, zinc, copper, sodium, or potassium. Such cyanation reactions are well known to those skilled in the art and can be carried out optionally in the presence of a metal catalyst. Cyanation with copper cyanide, known as Rosenmund-von Braun reactions, can be carried out with for example CuCN and compounds of formula (XVI), wherein X° is Br, or I, in a dipolar aprotic solvents such as DMF or NMP, at temperatures between 150 to 250 °C. Such reactions have been reported in Tetrahedron 1984, 40, 1433-1456. Milder cyanation reactions can be carried out using compounds of formula (XVI), wherein X° is I, Br, and Cl, with, for example, Zn(CN)2, KCN, NaCN, or K Fe(l ll)CNs] as cyanide sources, in the presence of Pd, Rh, or Fe catalysts. Such metal catalyzed cyanation reactions have been reported in Inorg. Chim. Acta 2018, 469, 408-423, and Chem. Soc. Rev. 2011 , 40, 5049- 5067. Compounds of formula (XXII) can be converted to compounds of formula (lie) by [3+2] cycloaddition with a metal azide, such as sodium azide, in a dipolar aprotic solvent such as DMF or NMP, optionally in the presence of a catalyst. Such reactions are well documented in the literature, for example Dalton Trans. 2024, 53, 5648-5657, Dalton Trans. 2024, 53, 5648-5657, ACS Omega 2024, 9, 19, 21626-21636 and references cited therein. Compounds of formula (lice) can be alkylated with compounds of formula (XXI) by methods described vide supra to yield compounds of formula (lief), (llcg), and (llch), which can be isolated as single compounds by, for example, chromatographic methods know to those skilled in the art. Compounds of formula (lice), (I Icf), (llcg), and (llch) are converted to compounds of formula (I) as described in Scheme 1 . Compounds of formula (XXII) are useful for preparation of further compounds of formula (II), concretely compounds of formula (I lei), (I Icj), (lick), (I lei), and (llcm) as shown in scheme 17.

[0153] Scheme 17

[0154] As shown in scheme 17, treatment of compounds of formula (XXII) with compounds of formula (XXIV), wherein R7is Ci-C4-alkyl leads to compounds of formula (XXIII). Such reactions are well known to those skilled in the art and conditions for performing these are described for example in Sci. Synth. 2005, 22, 379-488. Compounds of formula (XXIII) can be converted to compounds of formula (llci) by treatment with compounds of formula (XXV), wherein R6aand R6bare as previously defined, under conditions analogous to those described for example in J. Het. Chem. 1975, 12(3), 471-6. Compounds of formula (XXII) can also be treated with hydrazine, to yield compounds of formula (XXVI) which upon reaction with compounds of formula (XXVII) or (XXVI la) yield compounds of formula (llcj). Such reaction sequences can be carried out analogously to those reported in the literature (see J. Med. Chem. 2004, 47(19), 4645-4648). Alkylation of compounds of formula (llcj) with compounds of formula (XXI) leads to compounds of formula (lick), (llcl), and (Hem). All compounds of formula (II) described can be converted to compounds of formula (I) as described in Scheme 1.

[0155] Compounds of formula (II) wherein Q is Q14, namely compounds of formula (llco), can be prepared as shown in scheme 18.

[0156] Scheme 18

[0157] According to scheme 18, compounds of formula (XVI), wherein R2, R3, B1, B2, are defined as for compounds of formula(l), R01is Ci-C4-alkyl, and X° is halogen, can be converted to compounds of formula (XXVIII) by treatment with a metal azide, such as sodium azide, in a dipolar aprotic solvent such as DMF or DMSO, at temperatures between 25 to 120°C. Similar reactions are well known and have been published, for example in Chem. 2024, 10, 628-643. Compounds of formula (XXVIII) upon reaction with acetylenes of formula (XXIX), wherein R6aand R6bare as previously described using [3+2] cycloadditions described under scheme 15, leads to compounds of formula (Ho), which can be converted to compounds of formula (I) by methods described in scheme 1. A further synthesis of compounds of formula (I), wherein Q is Q6 is shown in Scheme 19.

[0158] Scheme 19 As shown in scheme 19, compounds of formula (XVI) can be reacted with compounds of formula (XXIX), under Pd catalysis to give compounds of formula (XXX) which can be deprotected under acidic conditions to give compounds of formula (XXXI). The latter compounds can be condensed with compounds of formula (XXXII) or (XXXIII) to give compounds of formula (lien). Compounds of formula (Hen) are converted to compounds of formula (I), wherein Q is Q6 according to the methods described in Scheme 1 .

[0159] Those skilled in the art will recognize that the compounds of formula (I) can be constructed in a different manner as shown in scheme 20.

[0160] As shown in scheme 20, reaction of compounds of formula (XVI) with compounds of formula (III) under conditions described in Scheme 1 , leads to compounds of formula (XXXIV). These can be converted to compounds of formula (I) by the methods described above.

[0161] Alternatively, compounds of formula (I) can be obtained by transformation of another, closely related, compound of formula (I) (or analogue thereof) using standard synthesis techniques known to the person skilled in the art. Non-exhaustive examples include oxidations, oxygenations, reductions, reductive deoxygenations, hydrogenations, hydrolysis, coupling reactions, aromatic nucleophilic or electrophilic substitution reactions, nucleophilic substitutions, deoxyfluorination, alkylation, radical addition, nucleophilic addition, condensation and halogenation.

[0162] The compounds of formula (I) and, where appropriate, the tautomers thereof, in each case in free form or in salt form, can, if appropriate, also be obtained in the form of hydrates and / or include other solvents, for example those which may have been used for the crystallization of compounds which are present in solid form.

[0163] As already indicated, surprisingly, it has now been found that the compounds of formula (I) of the present invention have, for practical purposes, a very advantageous level of biological activity for protecting plants against diseases that are caused by fungi.

[0164] The compounds of formula (I) according to the invention can be used in the agricultural sector and related fields of use, e.g., as active ingredients for controlling plant pests or on non-living materials for the control of spoilage microorganisms or organisms potentially harmful to man. The novel compounds are distinguished by excellent activity at low rates of application, by being well tolerated by plants and by being environmentally safe. They have very useful curative, preventive and systemic properties and can be used for protecting numerous cultivated plants. The compounds of formula (I) can be used to inhibit or destroy the pests that occur on plants or parts of plants (fruit, blossoms, leaves, stems, tubers, roots) of different crops of useful plants, while at the same time also protecting those parts of the plants that grow later, e.g., from phytopathogenic microorganisms. The present invention further relates to a method for controlling or preventing infestation of plants or plant propagation material and / or harvested food crops susceptible to microbial attack by treating plants or plant propagation material and / or harvested food crops wherein an effective amount a compound of formula (I) according to the invention is applied to the plants, to parts thereof or the locus thereof.

[0165] It is also possible to use a compound of formula (I) according to the invention as a fungicide. The term “fungicide” as used herein means a compound that controls, modifies, or prevents the growth of fungi. The term “fungicidally effective amount” where used means the quantity of such a compound or combination of such compounds that is capable of producing an effect on the growth of fungi. Controlling or modifying effects include all deviation from natural development, such as killing, retardation and the like, and prevention includes barrier or other defensive formation in or on a plant to prevent fungal infection.

[0166] It may also be possible to use compounds of formula (I) according to the invention as dressing agents for the treatment of plant propagation material, e.g., seed, such as fruits, tubers or grains, or plant cuttings, for the protection against fungal infections as well as against phytopathogenic fungi occurring in the soil. The propagation material can be treated with a composition comprising a compound of formula (I) before planting: seed, for example, can be dressed before being sown. The active compounds of formula (I) can also be applied to grains (coating), either by impregnating the seeds in a liquid formulation or by coating them with a solid formulation. The composition can also be applied to the planting site when the propagation material is being planted, for example, to the seed furrow during sowing. The invention relates also to such methods of treating plant propagation material and to the plant propagation material so treated.

[0167] Furthermore, the compounds of formula (I) according to the invention can be used for controlling fungi in related areas, for example in the protection of technical materials, including wood and wood related technical products, in food storage, in hygiene management.

[0168] In addition, the invention could be used to protect non-living materials from fungal attack, e.g., lumber, wall boards, and paint.

[0169] The compounds of formula (I) according to the invention are for example, effective against fungi and fungal vectors of disease as well as phytopathogenic bacteria and viruses. These fungi and fungal vectors of disease as well as phytopathogenic bacteria and viruses are for example: Altemaria spp. including Altemaria altemata and Altemaria solani, Aphanomyces spp., Ascochyta spp., Aspergillus spp., Aureobasidium spp., Bipolaris spp. including Bipolaris maydis and Bipolaris oryzae, Blastomyces dermatitidis, Blumeria graminis, Blumeria graminis f. sp. tritici, Bremia lactucae, Botryosphaeria spp. including B. dothidea, B. obtusa and B. squamosa, Botrytis spp. including B. cinerea and B. aim, Candida spp. including C. albicans, C. glabrata, C. krusei, C. lusitaniae, C. parapsilosis, and C. tropicalis, Cephaleuros spp. including Cephaloascus fragrans, Ceratocystis spp., Cercospora spp. including C. berticola, C. arachidicola and C. zeae-maydis, Cercosporidium personatum, Cladosporium spp., Clavibacter spp., Claviceps purpurea, Coccidioides immitis, Cochliobolus spp., Colletotrichum spp. including C. musae and C. lagenarium, Corynespora spp. including Corynespora cassiicola, Cryptococcus neoformans, Cytospora spp., Curvularia spp., Diaporthe spp. including Diaporthe miriciae (also known as Diaporthe ueckeri or Diaporthe ueckerae), D. macadamiae and D. longicolla, Didymella spp., Drechslera spp., Elsinoe spp., Epicoccum spp., Epidermophyton spp., Erwinia amylovora, Erysiphe spp. including E. cichoracearum and E. necator, Eutypa lata, Exobasidium spp., Exserohilum spp., Fulvia spp., Fusarium spp. including F. culmorum, F. graminearum, F. langsethiae, F. moniliforme, F. oxysporum, F. proliferatum, F. subglutinans, and F. solani, Gaeumannomyces graminis, Gibberella fujikuroi, Gloeodes pomigena, Gloeosporium musarum, Glomerella cingulata, Golovinomyces spp., Gymnosporangium spp., Helminthosporium spp., Hemileia spp., Laetisaria fuciformis, Leveillula taurica, Liberibacter spp., Marssonina spp., Microdochium nivale, Microsporum spp., Monilinia spp., Mucor spp., Mycosphaerella spp. including M. graminicola, and M. pomi, Neopestalotiopsis spp., Nothopassalora spp., Oculimacula spp., Oidium spp., Parastagonospora spp., Pectobacterium spp., Oncobasidium theobromaeon, Penicillium spp, Petriellidium spp., Pestalotiopsis spp., Phaeosphaeria spp., Phakopsora pachyrhizi, Phellinus spp., Phialophora spp., Phoma spp., Phomopsis spp., Phyllachora spp. including P. pomigena and P. maydis, Phyllactinia spp., Phyllosticta spp. including P. ampelicida and P. citricarpa, Plenodomus spp., Phytophthora spp. including P. infestans, Plasmopara spp., Pleospora spp., Podosphaera spp. including P. leucotricha and P. fuliginea, Polymyxa graminis, Polymyxa betae, Pseudocercospora spp., Pseudocercosporella herpotrichoides, Pseudomonas spp., Pseudoperonospora spp. including P. cubensis, and P. humuli, Pseudopeziza tracheiphila, Puccinia spp. including P. horde!, P. recondita, P. striiformis, and P. triticina, Pyrenopeziza spp., Pyrenophora spp. including P. teres and P. tritici-repentis, Pyricularia spp. including P. oryzae, Ralstonia spp., Pythium spp. including P. ultimum, Ramularia spp., Ramulariopsis spp., Rhizoctonia solani, Rhizomucor pusillus, Rhizopus arrhizus, Rhynchosporium spp., Scedosporium spp. including S. apiospermum and S. prolificans, Schizothyrium pomi, Sclerotinia spp., Sclerotium spp., Septoria spp., including S. nodorum, S. glycines, and S. tritici, Sphaerotheca macularis, Sphaerotheca fusca (Sphaerotheca fuliginea), Sporothrix sp., Stagonospora nodorum, Stemphylium spp., Stereum hirsutum, Thanatephorus cucumeris, Thielaviopsis spp. including T. basicola, Tilletia spp., Trichoderma spp. including T. harzianum, T. pseudokoningii, and T. viride, Trichophyton spp., Typhula spp., Uncinula necator, Urocystis spp., Uromyces spp., Ustilaginoidea spp., Ustilago maydis, Venturia spp., Verticillium spp., Xanthomonas spp., and Zymoseptoria spp. including Z. tritici (also called Septoria tritici or Mycosphaerella graminicola causing Septoria leaf spot

[0170] The compounds of formula (I) according to the invention may be used for example on turf, ornamentals, such as flowers, shrubs, broad-leaved trees, or evergreens, for example conifers, as well as for tree injection, pest management and the like.

[0171] Within the scope of present invention, target crops and / or useful plants to be protected typically comprise perennial and annual crops, such as berry plants for example blackberries, blueberries, cranberries, raspberries and strawberries; cereals for example barley, maize (corn), millet, oats, rice, rye, sorghum triticale and wheat; fibre plants for example cotton, flax, hemp, jute and sisal; field crops for example sugar and fodder beet, coffee, hops, mustard, oilseed rape (canola), poppy, sugar cane, sunflower, tea and tobacco; fruit trees for example apple, apricot, avocado, banana, cherry, citrus, nectarine, peach, pear and plum; grasses for example Bermuda grass, bluegrass, bentgrass, centipede grass, fescue, ryegrass, St. Augustine grass and Zoysia grass; herbs such as basil, borage, chives, coriander, lavender, lovage, mint, oregano, parsley, rosemary, sage and thyme; legumes for example beans, lentils, peas and soya beans; nuts for example almond, cashew, ground nut, hazelnut, peanut, pecan, pistachio and walnut; palms for example oil palm; ornamentals for example flowers, shrubs and trees; other trees, for example cacao, coconut, olive and rubber; vegetables for example asparagus, aubergine, broccoli, cabbage, carrot, cucumber, garlic, lettuce, marrow, melon, okra, onion, pepper, potato, pumpkin, rhubarb, spinach and tomato; and vines for example grapes.

[0172] The term "useful plants" is to be understood as also including useful plants that have been rendered tolerant to herbicides like bromoxynil or classes of herbicides (such as, for example, HPPD inhibitors, ALS inhibitors, for example primisulfuron, prosulfuron and trifloxysulfuron, EPSPS (5-enol-pyrovyl-shikimate-3-phosphate- synthase) inhibitors, GS (glutamine synthetase) inhibitors or PPG (protoporphyrinogen-oxidase) inhibitors) as a result of conventional methods of breeding or genetic engineering. An example of a crop that has been rendered tolerant to imidazolinones, e.g., imazamox, by conventional methods of breeding (mutagenesis) is Clearfield® summer rape (Canola). Examples of crops that have been rendered tolerant to herbicides or classes of herbicides by genetic engineering methods include glyphosate- and glufosinate-resistant maize varieties commercially available under the trade names RoundupReady®, Herculex I® and LibertyLink®.

[0173] The term "useful plants" is to be understood as also including useful plants which have been so transformed by the use of recombinant DNA techniques that they are capable of synthesizing one or more selectively acting toxins, such as are known, for example, from toxin-producing bacteria, especially those of the genus Bacillus.

[0174] Examples of such plants are: YieldGard® (maize variety that expresses a CrylA(b) toxin); YieldGard Rootworm® (maize variety that expresses a CrylllB(bl ) toxin); YieldGard Plus® (maize variety that expresses a CrylA(b) and a Cryll IB(b1 ) toxin); Starlink® (maize variety that expresses a Cry9(c) toxin); Herculex I® (maize variety that expresses a CrylF(a2) toxin and the enzyme phosphinothricin N-acetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate ammonium); NuCOTN 33B® (cotton variety that expresses a CrylA(c) toxin); Bollgard I® (cotton variety that expresses a CrylA(c) toxin); Bollgard II® (cotton variety that expresses a CrylA(c) and a CryllA(b) toxin); VIPCOT® (cotton variety that expresses a VIP toxin); NewLeaf® (potato variety that expresses a CrylllA toxin); Nature-Gard® Agrisure® GT Advantage (GA21 glyphosate-tolerant trait), Agrisure® CB Advantage (Bt11 corn borer (CB) trait), Agrisure® RW (corn rootworm trait) and Protecta®.

[0175] The term "crops" is to be understood as including also crop plants which have been so transformed using recombinant DNA techniques that they are capable of synthesizing one or more selectively acting toxins, such as are known, for example, from toxin-producing bacteria, especially those of the genus Bacillus.

[0176] Toxins that can be expressed by such transgenic plants include, for example, insecticidal proteins from Bacillus cereus or Bacillus popilliae; or insecticidal proteins from Bacillus thuringiensis, such as delta-endotoxins, e.g., CrylAb, CrylAc, Cry1 F, Cry1 Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), e.g., Vip1 , Vip2, Vip3 or Vip3A; or insecticidal proteins of bacteria colonizing nematodes, for example Photorhabdus spp. or Xenorhabdus spp., such as Photorhabdus luminescens, Xenorhabdus nematophilus; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins and other insect-specific neurotoxins; toxins produced by fungi, such as Streptomycetes toxins, plant lectins, such as pea lectins, barley lectins or snowdrop lectins; agglutinins; proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, papain inhibitors; ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such as 3-hydroxysteroidoxidase, ecdysteroid- UDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors, HMG-COA-reductase, ion channel blockers, such as blockers of sodium or calcium channels, juvenile hormone esterase, diuretic hormone receptors, stilbene synthase, bibenzyl synthase, chitinases and glucanases.

[0177] Further, in the context of the present invention there are to be understood by delta-endotoxins, for example CrylAb, CrylAc, Cry1 F, Cry1 Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), for example Vip1 , Vip2, Vip3 or Vip3A, expressly also hybrid toxins, truncated toxins, and modified toxins. Hybrid toxins are produced recombinantly by a new combination of different domains of those proteins (see, for example, W002 / 15701 ). Truncated toxins, for example a truncated CrylAb, are known. In the case of modified toxins, one or more amino acids of the naturally occurring toxin are replaced. In such amino acid replacements, preferably non-naturally present protease recognition sequences are inserted into the toxin, such as, for example, in the case of Cry3A055, a cathepsin-G-recognition sequence is inserted into a Cry3A toxin (see WG2003 / 018810).

[0178] Examples of such toxins or transgenic plants capable of synthesizing such toxins are disclosed, for example, in EP-0374753, WO93 / 07278, WO95 / 34656, EP0427529, EP0451878 and WG03 / 052073.

[0179] The processes for the preparation of such transgenic plants are generally known to a person skilled in the art and are described, for example, in the publications mentioned above. Cryl-type deoxyribonucleic acids and their preparation are known, for example, from WO95 / 34656, EP0367474, EP0401979 and WO90 / 13651 .

[0180] The toxin contained in the transgenic plants imparts to the plants tolerance to harmful insects. Such insects can occur in any taxonomic group of insects but are especially commonly found in the beetles (Coleoptera), two-winged insects (Diptera) and butterflies (Lepidoptera).

[0181] Transgenic plants containing one or more genes that code for an insecticidal resistance and express one or more toxins are known and some of them are commercially available. Examples of such plants are: YieldGard® (maize variety that expresses a CrylAb toxin); YieldGard Rootworm® (maize variety that expresses a Cry3Bb1 toxin); YieldGard Plus® (maize variety that expresses a CrylAb and a Cry3Bb1 toxin); Starlink® (maize variety that expresses a Cry9C toxin); Herculex I® (maize variety that expresses a Cry1 Fa2 toxin and the enzyme phosphinothricin N-acetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate ammonium); NuCOTN 33B® (cotton variety that expresses a CrylAc toxin); Bollgard I® (cotton variety that expresses a CrylAc toxin); Bollgard II® (cotton variety that expresses a CrylAc and a Cry2Ab toxin); VipCot® (cotton variety that expresses a Vip3A and a CrylAb toxin); NewLeaf® (potato variety that expresses a Cry3A toxin); NatureGard®, Agrisure® GT Advantage (GA21 glyphosate-tolerant trait), Agrisure® CB Advantage (Bt11 corn borer (CB) trait) and Protecta®.

[0182] Further examples of such transgenic crops are:

[0183] 1. Bt11 Maize from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10. Genetically modified Zea mays which has been rendered resistant to attack by the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of a truncated Cry 1 Ab toxin. Bt11 maize also transgenically expresses the enzyme PAT to achieve tolerance to the herbicide glufosinate ammonium.

[0184] 2. Bt176 Maize from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10. Genetically modified Zea mays which has been rendered resistant to attack by the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of a Cry1 Ab toxin. Bt176 maize also transgenically expresses the enzyme PAT to achieve tolerance to the herbicide glufosinate ammonium.

[0185] 3. MIR604 Maize from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10. Maize which has been rendered insect-resistant by transgenic expression of a modified Cry3A toxin. This toxin is Cry3A055 modified by insertion of a cathepsin-G-protease recognition sequence. The preparation of such transgenic maize plants is described in WG2003 / 018810.

[0186] 4. MON 863 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1 150 Brussels, Belgium, registration number C / DE / 02 / 9. MON 863 expresses a Cry3Bb1 toxin and has resistance to certain Coleoptera insects.

[0187] 5. IPC 531 Cotton from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C / ES / 96 / 02.

[0188] 6. 1507 Maize from Pioneer Overseas Corporation, Avenue Tedesco, 7 B-1160 Brussels, Belgium, registration number C / NL / 00 / 10. Genetically modified maize for the expression of the protein Cry1 F for achieving resistance to certain Lepidoptera insects and of the PAT protein for achieving tolerance to the herbicide glufosinate ammonium.

[0189] 7. NK603 x MON 810 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B 1 150 Brussels, Belgium, registration number C / GB / 02 / M3 / 03. Consists of conventionally bred hybrid maize varieties by crossing the genetically modified varieties NK603 and MON 810. NK603 x MON 810 Maize transgenically expresses the protein CP4 EPSPS, obtained from Agrobacterium sp. strain CP4, which imparts tolerance to the herbicide Roundup® (contains glyphosate), and also a CrylAb toxin obtained from Bacillus thuringiensis subsp. kurstaki which brings about tolerance to certain Lepidoptera, include the European corn borer.

[0190] The compounds of formula (I) according to the invention may be used in controlling or preventing phytopathogenic diseases, especially phytopathogenic fungi, especially phytopathogenic fungi on soybean plants. In one embodiment such soybean plants are genetically modified soybean plants.

[0191] In one embodiment the genetically modified plants are soybean plants. Examples of genetically modified plants of soybean are, but not limited to, Intacta®, lntacta®2, Intacta® Roundup Ready™ 2 Pro (lntacta®RR2 PRO), lntacta®2 Xtend™, Cultivance, Conkesta Soybean, Conkesta Enlist E3™ Soybean, Enlist™ Soybean, Enlist E3™ Soybean, Roundup Ready™ Soybean, Roundup Ready™ 2 Xtend™, Genuity® Roundup Ready™ 2 Xtend™, Genuity® Roundup Ready 2 Yield™, Herbicide-tolerant Soybean line, Optimum GAT™, Liberty Link™ Soybean, Vistive Gold™, Verdeca HB4 Soybean, Treus™, Plenish™. Transgenic soybean plants expressing toxins, for example insecticidal proteins such as delta-endotoxins, e.g., CrylAc (CrylAc Bt protein). Accordingly, this may include transgenic soybean plants comprising event MON87701 (disclosed in W02009 / 064652), event MON87701 x MON89788 (disclosed in WO2014 / 170327, e.g. commercially available as Intacta RR2 PRO® soybean), event MON87751 (disclosed in WO2014 / 201235), event DAS-44406-6 (e.g., commercially available as Enlist E3TM, DAS-44406-6, disclosed in WO2012 / 075426), or event DAS-81419-2 (described in WO2013 / 016527, e.g., commercially available as Conkesta™ soybean); event DAS-81419-2 x DAS-44406-6 (e.g., commercially available as Conkesta™ Enlist E3™ Soybean).

[0192] Furthermore, such a list of transgenic events is provided by the United States Department of Agriculture's (USDA) Animal and Plant Health Inspection Service (APHIS) and can be found on their website on the World Wide Web at aphis.usda.gov.

[0193] The compounds of formula (I) and compositions comprising said compounds, may be used in controlling or preventing phytopathogenic diseases, especially phytopathogenic fungi such as Altemaria spp. in various crops like fruits, vegetables, sunflower, rice, cotton, oilseed rape, canola, nuts and potatoes; Botrytis spp. in various crops like berries, fruits, sunflower, protein crops, vegetables and grapes; Powdery mildews like Uncinula necator, Blumeria graminis, Erysiphe spp. Leveillula taurica and Podosphaera spp. in various crops like grapes, vegetables, soybean, cereals, fruits, protein crops, sugar beet nuts and berry crops; Rusts like Puccinia spp. in various crops like cereals, corn, sugar beet, peanuts, sorghum, sugar cane, Sunflower and vegetables; Colletotrichum sp. in various crops like citrus and other fruits, protein crops, vegetables, cotton, coffee, grape, potato, berries, soybean and sugarcane; Pyrenophora sp in cereals like wheat, barley, rye, triticale and oat; Pyricularia sp. in cereals like rice and wheat; Sclerotinia sp. in various crops like vegetables, potato, soybean, canola, oilseed rape, protein crops, oil flax, sunflower and cereals; Cercospora sp. in various crops like fruits, vegetables, grape, protein crops, coffee, cotton, corn, tea, soybean, rice, peanuts and other nuts, Rhizoctani solani, Fusarium spp. in various crops like wheat and corn, in Zymoseptoria spp. in various crops like wheat.

[0194] The compounds of formula (XI), (XII), or (XIII), and compositions comprising said compounds, are suitable for controlling the following fungal diseases on soybeans and genetically modified soybeans, for example Bt soybeans: Altemaria spp. (Altemaria leaf spot); Ascochyta spp. (Leaf spots); Cercospora spp. (leaf spots), e.g. C. sojina or C. kikuchii; Colletotrichum spp. (teleomorph: Glomerella) (anthracnose), e.g. C. truncatum, C. cliviicola or C. gloeosporioides; Corynespora cassiicola (leaf spots); Dematophora (teleomorph: Rosellinia) necatrix (root and stem rot); Diaporthe spp., e.g. Diaporthe miriciae (also known as Diaporthe ueckeri or Diaporthe ueckerae), Diaporthe macadamiae and Diaporthe longicolla (damping off, seeds decay, anomaly); Erysiphe diffusa (powdery mildew); Fusarium (teleomorph: Gibberella) spp. (wilt, root or stem rot), e.g. F. tucumaniae and F. brasiliense (each causing sudden death syndrome on soybeans); Macrophomina phaseolina (syn. phaseoli) (root and stem rot); Peronospora spp. (downy mildew), e.g. P. manshurica; Phakopsora pachyrhizi and P. meibomiae (soybean rust); Phialophora spp., e.g. P. gregata (brown stem rot); Phomopsis spp., e.g. P. phaseoli (teleomorph: Diaporthe phaseolorum); Pythium spp. (damping-off); Phytophthora spp. (wilt, root, leaf, fruit and stem root), e.g. P. megasperma (syn. P. sojae); Rhizoctonia solani (root and stem rot); Sclerotinia spp. (stem rot or white mold); Septoria glycines (brown spot); S. rolfsii (syn. Athelia rolfsii) Thielaviopsis spp. (black root rot).

[0195] The term “locus” as used herein means fields in or on which plants are growing, or where seeds of cultivated plants are sown, or where seed will be placed into the soil. It includes soil, seeds, and seedlings, as well as established vegetation.

[0196] The term “plants” refers to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, stalks, foliage, and fruits.

[0197] The term “plant propagation material” is understood to denote generative parts of the plant, such as seeds, which can be used for the multiplication of the latter, and vegetative material, such as cuttings or tubers, for example potatoes. There can be mentioned for example seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes, and parts of plants. Germinated plants and young plants which are to be transplanted after germination or after emergence from the soil, may also be mentioned. These young plants can be protected before transplantation by a total or partial treatment by immersion. Preferably “plant propagation material” is understood to denote seeds.

[0198] The compounds of formula (I) according to the invention may be used in unmodified form or, preferably, together with the adjuvants conventionally employed in the art of formulation. To this end they may be conveniently formulated in known manner to emulsifiable concentrates, coatable pastes, directly sprayable or dilutable solutions or suspensions, dilute emulsions, wettable powders, soluble powders, dusts, granulates, and also encapsulations e.g., in polymeric substances. As with the type of the compositions, the methods of application, such as spraying, atomising, dusting, scattering, coating, or pouring, are chosen in accordance with the intended objectives and the prevailing circumstances. The compositions may also contain further adjuvants such as stabilizers, antifoams, viscosity regulators, binders or tackifiers as well as fertilizers, micronutrient donors or other formulations for obtaining special effects.

[0199] Suitable carriers and adjuvants, e.g., for agricultural use, can be solid or liquid and are substances useful in formulation technology, e.g., natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilizers. Such carriers are for example described in WO1997 / 33890.

[0200] Suspension concentrates are aqueous formulations in which finely divided solid particles of the active compound are suspended. Such formulations include anti-settling agents and dispersing agents and may further include a wetting agent to enhance activity as well an anti-foam and a crystal growth inhibitor. In use, these concentrates are diluted in water and normally applied as a spray to the area to be treated. The amount of active ingredient may range from 0.5% to 95% of the concentrate.

[0201] Wettable powders are in the form of finely divided particles which disperse readily in water or other liquid carriers. The particles contain the active ingredient retained in a solid matrix. Typical solid matrices include fuller’s earth, kaolin clays, silicas and other readily wet organic or inorganic solids. Wettable powders normally contain from 5% to 95% of the active ingredient plus a small amount of wetting, dispersing or emulsifying agent. Emulsifiable concentrates are homogeneous liquid compositions dispersible in water or other liquid and may consist entirely of the active compound with a liquid or solid emulsifying agent, or may also contain a liquid carrier, such as xylene, heavy aromatic naphthas, isophorone and other non-volatile organic solvents. In use, these concentrates are dispersed in water or other liquid and normally applied as a spray to the area to be treated. The amount of active ingredient may range from 0.5% to 95% of the concentrate.

[0202] Granular formulations include both extrudates and relatively coarse particles and are usually applied without dilution to the area in which treatment is required. Typical carriers for granular formulations include sand, fuller’s earth, attapulgite clay, bentonite clays, montmorillonite clay, vermiculite, perlite, calcium carbonate, brick, pumice, pyrophyllite, kaolin, dolomite, plaster, wood flour, ground corn cobs, ground peanut hulls, sugars, sodium chloride, sodium sulfate, sodium silicate, sodium borate, magnesia, mica, iron oxide, zinc oxide, titanium oxide, antimony oxide, cryolite, gypsum, diatomaceous earth, calcium sulfate and other organic or inorganic materials which absorb or which can be coated with the active compound. Granular formulations normally contain 5% to 25% of active ingredients which may include surface-active agents such as heavy aromatic naphthas, kerosene and other petroleum fractions, or vegetable oils; and / or stickers such as dextrins, glue or synthetic resins.

[0203] Dusts are free-flowing admixtures of the active ingredient with finely divided solids such as talc, clays, flours and other organic and inorganic solids which act as dispersants and carriers.

[0204] Microcapsules are typically droplets or granules of the active ingredient enclosed in an inert porous shell which allows escape of the enclosed material to the surroundings at controlled rates. Encapsulated droplets are typically 1 to 50 microns in diameter. The enclosed liquid typically constitutes 50 to 95% of the weight of the capsule and may include solvent in addition to the active compound. Encapsulated granules are generally porous granules with porous membranes sealing the granule pore openings, retaining the active species in liquid form inside the granule pores. Granules typically range from 1 millimetre to 1 centimetre and preferably 1 to 2 millimetres in diameter. Granules are formed by extrusion, agglomeration or prilling, or are naturally occurring. Examples of such materials are vermiculite, sintered clay, kaolin, attapulgite clay, sawdust, and granular carbon. Shell or membrane materials include natural and synthetic rubbers, cellulosic materials, styrene-butadiene copolymers, polyacrylonitriles, polyacrylates, polyesters, polyamides, polyureas, polyurethanes and starch xanthates.

[0205] Other useful formulations for agrochemical applications include simple solutions of the active ingredient in a solvent in which it is completely soluble at the desired concentration, such as acetone, alkylated naphthalenes, xylene and other organic solvents. Pressurized sprayers, wherein the active ingredient is dispersed in finely divided form as a result of vaporization of a low boiling dispersant solvent carrier, may also be used.

[0206] Suitable agricultural adjuvants and carriers that are useful in formulating the compositions of the invention in the formulation types described above are well known to a person skilled in the art.

[0207] Liquid carriers that can be employed include, for example, water, toluene, xylene, petroleum naphtha, crop oil, acetone, methyl ethyl ketone, cyclohexanone, acetic anhydride, acetonitrile, acetophenone, amyl acetate, 2- butanone, chlorobenzene, cyclohexane, cyclohexanol, alkyl acetates, diacetonalcohol, 1 ,2-dichloropropane, diethanolamine, p diethylbenzene, diethylene glycol, diethylene glycol abietate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, N,N-dimethyl formamide, dimethyl sulfoxide, 1 ,4- dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, diproxitol, alkyl pyrrolidinone, ethyl acetate, 2-ethyl hexanol, ethylene carbonate, 1 ,1 ,1 -trichloroethane, 2-heptanone, alpha pinene, d-limonene, ethylene glycol, ethylene glycol butyl ether, ethylene glycol methyl ether, gammabutyrolactone, glycerol, glycerol diacetate, glycerol monoacetate, glycerol triacetate, hexadecane, hexylene glycol, isoamyl acetate, isobornyl acetate, isooctane, isophorone, isopropyl benzene, isopropyl myristate, lactic acid, laurylamine, mesityl oxide, methoxy-propanol, methyl isoamyl ketone, methyl isobutyl ketone, methyl laurate, methyl octanoate, methyl oleate, methylene chloride, m-xylene, n-hexane, n-octylamine, octadecanoic acid, octyl amine acetate, oleic acid, oleylamine, o-xylene, phenol, polyethylene glycol (PEG400), propionic acid, propylene glycol, propylene glycol monomethyl ether, p-xylene, toluene, triethyl phosphate, triethylene glycol, xylene sulfonic acid, paraffin, mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, methanol, ethanol, isopropanol, and higher molecular weight alcohols such as amyl alcohol, tetrahydrofurfuryl alcohol, hexanol, octanol, etc., ethylene glycol, propylene glycol, glycerine and N- methyl-2-pyrrolidinone. Water is generally the carrier of choice for the dilution of concentrates.

[0208] Suitable solid carriers include, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, kieselguhr, chalk, diatomaxeous earth, lime, calcium carbonate, bentonite clay, fuller’s earth, cotton seed hulls, wheat flour, soybean flour, pumice, wood flour, walnut shell flour and lignin.

[0209] A broad range of surface-active agents are advantageously employed in both said liquid and solid compositions, especially those designed to be diluted with carrier before application. These agents, when used, normally comprise from 0.1 % to 15% by weight of the formulation. They can be anionic, cationic, non-ionic, or polymeric in character and can be employed as emulsifying agents, wetting agents, suspending agents or for other purposes. Typical surface-active agents include salts of alkyl sulfates, such as diethanolammonium lauryl sulfate; alkylarylsulfonate salts, such as calcium dodecylbenzenesulfonate; alkylphenol-alkylene oxide addition products, such as nonylphenol-C.sub. 18 ethoxylate; alcohol-alkylene oxide addition products, such as tridecyl alcohol-C.sub. 16 ethoxylate; soaps, such as sodium stearate; alkylnaphthalenesulfonate salts, such as sodium dibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinate salts, such as sodium di(2 ethylhexyl) sulfosuccinate; sorbitol esters, such as sorbitol oleate; quaternary amines, such as lauryl trimethylammonium chloride; polyethylene glycol esters of fatty acids, such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; and salts of mono and dialkyl phosphate esters.

[0210] Other adjuvants commonly utilized in agricultural compositions include crystallisation inhibitors, viscosity modifiers, suspending agents, spray droplet modifiers, pigments, antioxidants, foaming agents, anti-foaming agents, light-blocking agents, compatibilizing agents, antifoam agents, sequestering agents, neutralising agents and buffers, corrosion inhibitors, dyes, odorants, spreading agents, penetration aids, micronutrients, emollients, lubricants, and sticking agents. In addition, further, other biocidal active ingredients or compositions may be combined with the compositions of the invention and used in the methods of the invention and applied simultaneously or sequentially with the compositions of the invention. When applied simultaneously, these further active ingredients may be formulated together with the compositions of the invention or mixed in, for example, the spray tank. These further biocidal active ingredients may be fungicides, herbicides, insecticides, bactericides, acaricides, nematicides and / or plant growth regulators.

[0211] Pesticidal agents are referred to herein using their common name are known, for example, from "The Pesticide Manual", 15th Ed., British Crop Protection Council 2009.

[0212] In addition, the compositions of the invention may also be applied with one or more systemically acquired resistance inducers (“SAR” inducer). SAR inducers are known and described in, for example, United States Patent No. US 6,919,298 and include, for example, salicylates and the commercial SAR inducer acibenzolar- S-methyl.

[0213] The compounds of formula (I) according to the invention are normally used in the form of agrochemical compositions and can be applied to the crop area or plant to be treated, simultaneously or in succession with further compounds. These further compounds can be e.g., fertilizers or micronutrient donors or other preparations, which influence the growth of plants. They can also be selective herbicides or non-selective herbicides as well as insecticides, fungicides, bactericides, nematicides, molluscicides or mixtures of several of these preparations, if desired together with further carriers, surfactants or application promoting adjuvants customarily employed in the art of formulation.

[0214] The compounds of formula (I) according to the invention may be used in the form of (fungicidal) compositions for controlling or protecting against phytopathogenic microorganisms, comprising as active ingredient at least one compound of formula (I) or of at least one preferred individual compound as defined herein, in free form or in agrochemical usable salt form, and at least one of the above-mentioned adjuvants.

[0215] The invention therefore provides a composition, preferably a fungicidal composition, comprising at least one compound of formula (I) according to the invention, an agriculturally acceptable carrier and optionally an adjuvant. An agricultural acceptable carrier is for example a carrier that is suitable for agricultural use. Agricultural carriers are well known in the art. Preferably, said composition may comprise at least one or more pesticidal-active compounds, for example an additional fungicidal active ingredient in addition to the compound of formula (I).

[0216] The compound of formula (I) according to the invention may be the sole active ingredient of a composition or it may be admixed with one or more additional active ingredients such as a pesticide, fungicide, synergist, herbicide, or plant growth regulator where appropriate. An additional active ingredient may, in some cases, result in unexpected synergistic activities.

[0217] Examples of suitable additional active ingredients include the following: acycloamino acid fungicides, aliphatic nitrogen fungicides, amide fungicides, anilide fungicides, antibiotic fungicides, aromatic fungicides, arsenical fungicides, aryl phenyl ketone fungicides, benzamide fungicides, benzanilide fungicides, benzimidazole fungicides, benzothiazole fungicides, botanical fungicides, bridged diphenyl fungicides, carbamate fungicides, carbanilate fungicides, conazole fungicides, copper fungicides, dicarboximide fungicides, dinitrophenol fungicides, dithiocarbamate fungicides, dithiolane fungicides, furamide fungicides, furanilide fungicides, hydrazide fungicides, imidazole fungicides, mercury fungicides, morpholine fungicides, organophosphorous fungicides, organotin fungicides, oxathiin fungicides, oxazole fungicides, phenylsulfamide fungicides, polysulfide fungicides, pyrazole fungicides, pyridine fungicides, pyrimidine fungicides, pyrrole fungicides, quaternary ammonium fungicides, quinoline fungicides, quinone fungicides, quinoxaline fungicides, strobilurin fungicides, sulfonanilide fungicides, thiadiazole fungicides, thiazole fungicides, thiazolidine fungicides, thiocarbamate fungicides, thiophene fungicides, triazine fungicides, triazole fungicides, triazolopyrimidine fungicides, urea fungicides, valinamide fungicides, and zinc fungicides.

[0218] The following mixtures of the compounds of formula (I), or compounds selected from the compounds listed in Tables C-1 to C-56, or compounds listed in Table P (below), with active ingredients are preferred: (4E,10Z)- tetradeca-4, 10-dienyl acetate, (7E,9Z)-dodeca-7,9-dien-1-yl acetate, (E)-6-methylhept-2-en-4-ol, (E)-dec-5-en-

[0219] 1-yl acetate with (E)-dec-5-en-1-ol, (E)-tridec-4-en-1-yl acetate, (S)-bioallethrin, (Z)-dodec-7-en-1-yl acetate, (Z)-hexadec-l 1-en-1-yl acetate, (Z)-hexadec-l 1-enal, (Z)-hexadec-13-en-11-yn-1-yl acetate, (Z)-icos-13-en- 10-one, (Z)-tetradec-7-en-1 -al, (Z)-tetradec-9-en-1-ol, (Z)-tetradec-9-en-1-yl acetate, 1 ,1-bis(4-chlorophenyl)-

[0220] 2-ethoxyethanol, 1 -(2-chlorophenyl)-3,3-dimethyl-2-(1 ,2,4-triazol-1 -ylmethyl)butan-2-ol, 1 -(5-bromo-2-pyridyl)- 2-(2,4-difluorophenyl)-1 , 1 -difluoro-3-(1 ,2,4-triazol-1 -yl)propan-2-ol, 1 -hydroxy-1 H-pyridine-2-thione, 1 - methylcyclopropene, 1 -naphthaleneacetamide, 1 -naphthylacetic acid, 2,2-dichlorovinyl 2-ethylsulfinylethyl methyl phosphate, 2,4-D, 2,4-DB, 2,6-dichloro-N-(4-trifluormethylbenzyl)benzamide, 2-(1 ,3-dithiolan-2- yl)phenyl dimethylcarbamate, 2-(2-butoxyethoxy)ethyl piperonylate, 2-(4,5-dimethyl-1 ,3-dioxolan-2-yl)phenyl methylcarbamate, 2-(difluoromethyl)-N-((3R)-1 ,1 ,3-trimethylindan-4-yl) pyridine-3-carboxamide, 2- (octylthio)-ethanol, 2-bromo-2-bromomethyl-pentanedinitrile, 2-chlorovinyl diethyl phosphate, 2-imidazolidone, 2-methyl(prop-2-ynyl)aminophenyl methylcarbamate, 2-thiocyanatoethyl laurate, 3-(4-chlorophenyl)-5- methylrhodanine, 3-(difluoromethyl)-1-methyl-N-[1 ,1 ,3-trimethylindan-4-yl]pyrazole-4-carboxamide, 3- (difluoromethyl)-N-(7-fluoro-1 ,1 ,3,3-tetramethyl-indan-4-yl)-1-methyl-pyrazole-4-carboxamide, 3-(difluoro- methyl)-N-(7-fluoro-1 ,1 ,3,3-tetramethyl-indan-4-yl)-1-methyl-pyrazole-4-carboxamide, 3-chloro-6-methyl-5- phenyl-4-(2,4,6-trifluorophenyl)pyridazine, 3-methyl-1-phenylpyrazol-5-yldimethyl-carbamate, 3-phenylphenol, 4,5-dichlorodithiol-3-one, 4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyridazine-3-carbonitrile, 4-(2-bromo-4- fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl)-2,5-dimethyl-pyrazol-3-amine, 4-(quinoxalin-2-ylamino)benzene sulfonamide, 4-[[6-[2-(2,4-difluorophenyl)-1 ,1-difluoro-2-hydroxy-3-(1 ,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy] benzonitrile, 4-chloro-2-(2-chloro-2-methyl-propyl)-5-[(6-iodo-3-pyridyl)methoxy]pyridazin-3-one, 4-CPA, 4- methyl(prop-2-ynyl)amino-3,5-xylyl methylcarbamate, 4-methylnonan-5-ol with 4-methylnonan-5-one, 4- phenylphenol, 5-(1 ,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone, 5-amino-1 ,3,4-thiadiazole-2-thiol, 5-fluoro-2- (p-tolylmethoxy)pyrimidin-4-amine, 5-hydroxy-6-methyl-4-(((E)-pyridin-3-ylmethylene)amino)-4,5-dihydro- 1 ,2,4-triazin-3(2H)-one, 5-methyl-6-thioxo-1 ,3,5-thiadiazinan-3-ylacetic acid, 8-hydroxyquinoline sulfate, 11 - ethyl-10,12-dioxo-2,5,8-trithia-4,11-diazatricyclo[7.3.0.03,7]dodeca-1 (9),3,6-triene-6-carbonitrile, 14-methyl octadec-1-ene, [(9Z,11 E)-tetradeca-9,11 -dienyl] acetate, [(Z)-dodec-9-enyl] acetate, abamectin, acephate, acequinocyl, acetamiprid, acethion, acetoprole, acibenzolar, acibenzolar-S-methyl, acrinathrin, Adoxophyes orana GV, Agrobacterium radiobacter, alanycarb, albendazole, aldicarb, allethrin, allosamidin, allyl alcohol, allyxycarb, alpha-ecdysone, alpha-multistriatin, Amblyseius spp., ametoctradin, amidithion, amidoflumet, amidothioate, aminocarb, aminotipyr, amisulbrom, amiton, amiton hydrogen oxalate, amitraz, anabasine, Anagrapha falcifera NPV, Anagrus atomus, ancymidol, anilazine, anisiflupurin, anthraquinone, antu, Aphelinus abdominalis, Aphidius colemani, Aphidoletes aphidimyza, athidathion, aureofungin, Autographa californica NPV, avermectin B1a, azaconazole, azadirachtin A, azafenidin, azamethiphos, azinphos-ethyl, azinphos- methyl, azithiram, azoxystrobin, Bacillus sphaericus (Neide), Bacillus thuringiensis, Bacillus thuringiensis delta endotoxin, Bacillus thuringiensis ssp. aizawai, baculovirus, barthrin, Beauveria brongniartii, benalaxyl, benalaxyl-M, benazepril, benclothiaz, benfuracarb, benomyl, bensultap, benthiavalicarb, benzalkonium chloride, benzamorf, benzothiostrobin, benzovindiflupyr, beta-cyfluthrin, beta-cypermethrin, bethoxazin, bifemetstrobin, bifenazate, bifenthrin, binapacryl, bioallethrin, bioethanomethrin, biopermethrin, bioresmethrin, bisthiosemi, bistrifluron, bitertanol, bixafen, blasticidin-S, borax, bordeaux mixture, boscalid, brodifacoum, brofenvalerate, brofluthrinate, bromadiolone, bromfenvinfos, bromophos, bromophos-ethyl, bromuconazole, bufencarb, bupirimate, buprofezin, buserelin, busulfan, but-3-ynyl N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl- methylene]amino]oxymethyl]-2-pyridyl]carbamate, butacarb, butathiofos, butocarboxim, butonate, butopyronoxyl, butoxy(polypropylene glycol), butoxycarboxim, butylamine, cadusafos, calciferol, calcium phosphate, calcium polysulfide, cambendazole, captafol, captan, carbanolate, carbaryl, carbendazim, carbendazim hydrochloride, carbofuran, carbosulfan, carboxin, carprofen, carpropamid, cartap, cartap hydrochloride, cefalexin, cefovecin, cefquinome, ceftiour, cestex, cevadine, chinomethionat, chitosan, chlobenthiazone, chloralose, chlorantraniliprole, chlorbenside, chlordimeform, chlorethephon, chlorethoxyfos, chlorfenapyr, chlorfenazole, chlorfentazine, chlorfenvinphos, chlorfluazuron, chlormephos, chlormequat, chlorodimeform hydrochloride, chloroinconazide, chloromebuform, chloromethiuron, chloroneb, chlorothalonil, chlorphoxim, chlorprazophos, chlorpyrifos, chlorpyrifos-methyl, chlortetracycline, chlorthiophos, chlozolinate, cholecalciferol, chromafenozide, Chrysoperla carnea, cinerin, cinerin I, cinerin II, cis-jasmone, cis-resmethrin, cismethrin, clenbuterol, climbazole, cloethocarb, clofencet, clorsulon, clothianidin, clozylacon (acetamide), codlelure, copper acetate, copper hydroxide, copper naphthenate, copper octanoate, copper oleate, copper oxide, copper oxychloride, copper silicate, copper sulfate, copper(ll) carbonate, coumachlor, coumafene, coumafuryl, Coumatetralyl, coumethoxystrobin (jiaxiangjunzhi), coumithoate, coumoxystrobin, cryolite, Cryptolaemus montrouzieri, cuelure, cufraneb, cuprous(l) oxide, cyanofenphos, cyanthoate, cyazofamid, cybutryne, cyclafuramid, cyclethrin, cyclobutrifluram, Cydia pomonella GV, cyenopyrafen, cyflufenamid, cyflumetofen, cyfluthrin, cyhalothrin, cymiazole, cymoxanil, cypermethrin (alphametrin), cyphenothrin, cyproconazole, cyprodinil, cyprodinil, cyromazine, cytokinins, D-tetramethrin, Dacnusa sibirica, DAEP, dazomet, DCPM, debacarb, decarbofuran, deltamethrin, demephion-O, demephion-S, demeton-O, demeton- S, demeton-S-methyl, demeton-S-methylsulphon, diafenthiuron, dialifos, diazinon, dibutyl adipate, dibutyl phthalate, dibutyl succinate, dicapthon, dichlobentiazox, dichlofluanid, dichlone, dichlorprop, dichlorvos, dichlozoline, diclocymet, diclomezine, dicloran, dicofol, dicresyl, dicrotophos, dicyclanil, dicyclopentadiene, diethofencarb, diethyltoluamide, difenacoum, difenoconazole, difenzoquat, difethialone, diflovidazin, diflubenzuron, diflumetorim, Diglyphus isaea, dimatif, dimefluthrin, dimetan, dimethachlon, dimethipin, dimethirimol, dimethoate, dimethomorph, dimethrin, dimethyl disulfide, dimethyl phthalate, dimetilan, dimoxystrobin, dinactin, diniconazole, diniconazole-M, dinobuton, dinocap, dinocton, dinoseb, dinotefuran, diofenolan, dioxabenzofos, diphenylamine, dipyrithione, disparlure, disulfiram, disulfoton, ditalimfos, dithianon, dithicrofos, dithiocarbamate, dodec-8-en-1-yl acetate, dodemorph, dodicin, dodine, dofenapyn, dominicalure, doramectin, drazoxolon, DSP, ecdysterone, edifenphos, emamectin benzoate, EMPC, empenthrin, Encarsia formosa, endosulfan, endothal, endothion, enestroburin (enoxastrobin), enrofloxacin, entomopathogenic bacteria, entomopathogenic fungi, entomopathogenic virus, EPBP, epoxiconazole, eprinomectin, Eretmocerus eremicus, esfenvalerate, etaconazole, ethaboxam, ethiofencarb, ethion, ethiprole, ethirimol, ethoate-methyl, ethoprophos, ethoxyquin, ethyl 4-methyloctanoate, ethyl formate, ethyl hexanediol, etofenprox, etoxazole, etridiazole, etrimfos, eugenol, eurax, EXD, exo-brevicomin, famoxadone, famphur, farnesol with nerolidol, febantel, fenamidone, fenaminstrobin, fenamiphos, fenarimol, fenazaquin, fenbendazole, fenbuconazole, fenbutatin oxide, feneptamidoquin, fenethacarb, fenfluthrin, fenfuram, fenhexamid, fenitrothion, fenobucarb, fenopyramid, fenothiocarb, fenoxacrim, fenoxanil, fenoxycarb, fenpiclonil, fenpicoxamid, fenpirithrin, fenpropathrin, fenpropidin, fenpropimorph, fenpyrazamine, fenpyroximate, fensulfothion, fenthion, fenthion- ethyl, fentin, fentin acetate, fentin chloride, fentin hydroxide, fenvalerate, ferbam, ferimzone, ferric phosphate, fipronil, flocoumafen, flonicamid, florfenicol, florylpicoxamid, fluacrypyrim, fluazinam, fluazuron, flubendazole, flubendiamide, flubeneteram, flubenzimin, flucycloxuron, flucycloxuron, flucythrinate, fludioxonil, fluenetil, flufenerim, flufenoxuron, flufenoxystrobin, flufenprox, fluindapyr, flumetralin, flumetylsulforim, flumorph, fluopicolide, fluopimomide, fluopyram, fluoroimide, fluoxapiprolin, fluoxastrobin, fluoxytioconazole, flupyrazofos, fluquinconazole, flusilazole, flusulfamide, flutianil, flutolanil, flutriafol, fluxapyroxad, folpet, fonofos, forchlorfenuron, formaldehyde, formetanate, formetanate hydrochloride, formothion, formparanate, fosetyl, fosetyl-aluminium, fosmethilan, fosthiazate, fosthietan, frontalin, fuberidazole, furalaxyl, furametpyr, furathiocarb, furethrin, furfural, galquin, gibberellic acid, glyodin, glyphosate, grandlure I, grandlure II, grandlure III, grandlure IV, guazatine triacetate, halfenprox, halofenozide, hemel, heptenophos, Heterorhabditis bacteriophora and H. megidis, hexaconazole, hexadecyl cyclopropanecarboxylate, hexaflumuron, hexalure, hexamide, hexythiazox, Hippodamia convergens, huanjunzuo (rac-(1 S,2S)-1-(4-chlorophenyl)-2-(1 ,2,4-triazol- 1-yl)cycloheptanol), hydramethylnon, hydrated lime (calcium hydroxide), hymexazol, hyquincarb, icaridin, imanin (hypericin), imazalil, imazalil sulfate, imibenconazole, imidacloprid, iminoctadine, indoxacarb, inpyrfluxam, iodocarb, ipconazole, ipfentrifluconazole, ipflufenoquin, iprobenfos (IBP), iprodione, iprovalicarb, ipsdienol, ipsenol, IPSP, isamidofos, isazofos, isocarbophos, isofetamid, isoflucypram, Isolan, isoprocarb, isoprothiolane, isopyrazam, isothioate, isotianil, isoxathion, ivermectin, japonilure, jasmolin I, jasmolin II, juvenile hormone I, juvenile hormone II, juvenile hormone III, kadethrin, kanamycin, kasugamycin, kasugamycin hydrochloride hydrate, kinetin, kinoprene, kresoxim-methyl, kurstaki, lambda-cyhalothrin, Leptomastix dactylopii, leptophos, levamisole, lineatin, lirimfos, looplure, lufenuron, Ivbenmixianan, lythidathion, m-cumenyl methylcarbamate, Macrolophus caliginosus, magnesium phosphide, malathion, maleic hydrazide, malonoben, Mamestra brassicae NPV, mancopper, mancozeb, mandestrobin, mandipropamid, maneb, mazidox, mebendazole, mecarbam, mecarphon, medlure, mefentrifluconazole, megatomoic acid, meloxicam, menazon, mepanipyrim, meperfluthrin, mephosfolan, mepiquat, mepronil, meptyldinocap, mesulfenfos, metaflumizone, metalaxyl, metalaxyl-M, metaldehyde, metam, metam-potassium, metam-sodium, Metaphycus helvolus, Metarhizium anisopliae var. acridum, Metarhizium anisopliae var. anisopliae, metarylpicoxamid, metconazole, methacrifos, methamidophos, methasulfocarb, methidathion, methiocarb, methiotepa, methocrotophos, methomyl, methoprene, methoquin-butyl, methothrin, methoxyfenozide, methyl apholate, methyl eugenol, methyl iodide, methyl neodecanamide, metiram, metofluthrin, metolcarb, metominostrobin, metoxadiazone, metrafenone, metyltetraprole, mevinphos, mexacarbate, MGK 264, milbemycin, milbemycin oxime, monocrotophos, morantel tartrate, morzid, moxidectin, muscalure, myclobutanil, myclozolin, Myrothecium verrucaria composition, N-[2-[2,4-dichloro-phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4- carboxamide, N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-[(2-isopropylphenyl)methyl]-1-methyl-pyrazole-4- carboxamide, nabam, naled, NC-170, nemadectin, Neodiprion sertifer NPV and N. lecontei NPV, niclosamide- olamine, nicotine, nicotine sulfate, nikkomycins, nitenpyram, nithiazine, nitrapyrin, nitrilacarb, nitrothal- isopropyl, norbormide, nornicotine, novaluron, noviflumuron, nuarimol, O,O,O',O'-tetrapropyl dithiopyrophosphate, octadeca-2,13-dien-1-yl acetate, octadeca-2,13-dien-1-yl acetate, octhilinone, ofurace, oleic acid, omethoate, orfralure, Orius spp., orysastrobin, osthol, ostramone, oxadixyl, oxamate, oxamyl, oxantel pamoate, oxasulfuron, oxathiapiprolin, oxfendazole, oxibendazole, oxine copper, oxolinic acid, oxpoconazole, oxycarboxin, oxydemeton-methyl, oxydeprofos, oxydisulfoton, oxytetracycline, oxytetracycline dihydrate, paclobutrazol, Paecilomyces fumosoroseus, paraoxon, parathion, parathion-methyl, parbendazole, pefurazoate, penconazole, pencycuron, penethamate, penflufen, penthiopyrad, permethrin, petroleum oils, PH 60-38, phenamacril, phenthoate, phorate, phosacetim, phosalone, phosfolan, phosglycin, phosmet, phosnichlor, phosphamidon, phosphocarb, phosphonic acid, phosphorus, phoxim, phoxim-methyl, phthalide, Phytoseiulus persimilis, picarbutrazox, picoxystrobin, pimobendan, pindone, piperalin, piperonyl butoxide, piprotal, pirimetaphos, pirimicarb, pirimiphos-methyl, polycarbamate, polynactin, polyoxin B, polyoxin d, potassium ethylxanthate, potassium hydroxyquinoline sulfate, praziquantel, precocene I, precocene II, precocene III, primidophos, probenazole, prochloraz, procymidone, profenofos, profluthrin, prohexadione, prohexadione-calcium, promacyl, promecarb, propamidine, propamocarb, propaphos, propargite, propetamphos, propiconazole, propineb, propionic acid, propoxur, propyl isomer, proquinazid, prothidathion, prothioconazole, prothiofos, prothoate, protrifenbute, pydiflumetofen, pymetrozine, pyraclofos, pyraclostrobin, pyrafluprole, pyrametostrobin, pyrantel pamoate, pyraoxystrobin, pyrapropoyne, pyraziflumid, pyrazophos, pyrazoxone, pyresmethrin, pyrethrin I, pyrethrin II, pyrethrins (natural products), pyrethroids (natural products), pyribencarb, pyridaben, pyridachlometyl, pyridalyl, pyridaphenthion, pyridin-4-amine, pyrifenox, pyrifluquinazon, pyrimethanil, pyrimidifen, pyrimorph, pyriofenone, pyriprole, pyriproxyfen, pyrisoxazole, pyroquilon, quassia, quinaminoprole, quinalphos, quinalphos-methyl, quinoclamine, quinofumelin, quinonamid, quinothion, quinoxyfen, quintozene, R-1492, R-metalaxyl, Reynoutria sachalinensis extract, ribavirin, rotenone, ryanodine (ryania), sabadilla, schradan, scilliroside, seboctylamine, sedaxane, selamectin, sesamex, sesamolin, siglure, silafluofen, silthiofam, simeconazole, p-sitosterol, sodium tetrathiocarbonate, sophamide, sordidin, spinetoram, spinosad, spirodiclofen, spiromesifen, spirotetramat, spiroxamine, Steinernema bibionis, Steinernema carpocapsae, Steinernema feltiae, Steinernema glaseri, Steinernema riobrave, Steinernema riobravis, Steinernema scapterisci, Steinernema spp., streptomycin, streptomycin sesquisulfate, sulcatol, sulcofuron, sulfiram, sulfur, sulprofos, tar oils, tau-fluvalinate, TCMTB, TDE, tebuconazole, tebufenozide, tebufenpyrad, tebufloquin, tebupirimfos, tecnazene, teflubenzuron, tefluthrin, temephos, terallethrin, terbam, terbufos, tetrachlorvinphos, tetraconazole, tetradec-11-en-1-yl acetate, tetradifon, tetramethrin, tetramethylfluthrin, tetranactin, thiabendazole, thiacloprid, thiadiazole copper, thiamethoxam, thiapronil, thicrofos, thicyofen, thidiazuron, thifluzamide, thiocarboxime, thiocyclam, thiocyclam hydrogen oxalate, thiodicarb, thiofanox, thiometon, thiophanate, thiophanate-methyl, thioquinox, thiosultap, thiosultap-disodium, thiram, thuringiensin, tiadinil, tiamulin, tioxymid, tolclofos-methyl, tolfenpyrad, tolprocarb, tolylfluanid, tralomethrin, transpermethrin, tretamine, triadimefon, triadimenol, triarathene, triazamate, triazophos, triazoxide, tribufos, trichlorfon, trichlormetaphos-3, trichloronat, Trichogramma spp., triclabendazole, triclopyricarb, tricyclazole, tridemorph, trifenmorph, trifloxystrobin, triflumizole, triflumuron, triforine, trimedlure, trimedlure A, trimedlure B1 , trimedlure B2, trimedlure C, trimethacarb, trinactin, trinexapac, trinexapac-ethyl, trioxyflanilide, triprene, triticonazole, trunc-call, tulathromycin, Typhlodromus occidentalis, uniconazole, uredepa, validamycin, valifenalate, vamidothion, vaniliprole, veratridine, veratrine, verbutin, Verticillium lecanii, vinclozolin, XMC, xylenols, zeatin, zeta-cypermethrin, zhongshengmycin, zinc naphthenate, zinc thiazole, zineb, ziram, zolaprofos, zoxamide, 2-(difluoromethyl)-N-[(3S)-3-ethyl-1 ,1-dimethyl-indan-4-yl]pyridine-3- carboxamide (this compound may be prepared from the methods described in WO 2014 / 095675), methyl 3- [(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1 ,2,4-triazol-1-ylmethyl)cyclopentanecarboxylate (this compound may be prepared from the methods described in WO 2019 / 093522), methyl (2R)-2-[2-chloro-4-(4- chlorophenoxy)phenyl]-2-hydroxy-3-(1 ,2,4-triazol-1-yl)propanoate (this compound may be prepared from the methods described in WO 2019 / 093522), 5-[5-(difluoromethyl)-1 ,3,4-oxadiazol-2-yl]-N-[1-(2,6- difluorophenyl)cyclopropyl]pyrimidin-2-amine (this compound may be prepared from the methods described in WO 2021 / 255093), aminopyrifen (this compound may be prepared from the methods described in WO 2014 / 006945), dipymetitrone (this compound may be prepared from the methods described in WO 2011 / 138281 ), 1 -[6-(difluoromethyl)-5-methyl-3-pyridyl]-4,4-difluoro-3,3-dimethyl-isoquinoline (this compound may be prepared from the methods described in WO 2017 / 016915), 1 -[4-(difluoromethoxy)-2-methyl-phenyl]- 2-(1 ,2,4-triazol-1-yl)-1-[1-(trifluoromethyl)cyclopropyl] ethanol (this compound may be prepared from the methods described in WO 2021 / 249800), 1 -[2-chloro-4-(difluoromethoxy)phenyl]-2-(1 ,2,4-triazol-1-yl)-1-[1- (trifluoromethyl)cyclopropyl]ethanol (this compound may be prepared from the methods described in WO 2021 / 249800), 1-(5,6-dimethyl-3-pyridyl)-4,4-difluoro-3,3-dimethyl-isoquinoline (this compound may be prepared from the methods described in WO 2017 / 016915), N-methyl-4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3- yl]benzenecarbothioamide (this compound may be prepared from the methods described in WO 2015 / 185485), 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]acetamide (this compound may be prepared from the methods described in WO 2017 / 178245), flufenoxadiazam, N-methyl-4-[5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl]benzamide (this compound may be prepared from the methods described in WO 2015 / 185485), (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide (this compound may be prepared from the methods described in WO 2018 / 153707), (Z,2E)-5-[1-(4- chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide (this compound may be prepared from the methods described in WO 2013 / 092224), methyl (2E)-2-methoxyimino-2-[3-methyl-2-[[(E)-1-[4- (trifluoromethyl)-2-pyridyl]ethylideneamino]oxymethyl]phenyl]acetate (this compound may be prepared from the methods described in WO 2022 / 033906), (2E)-2-methoxyimino-N-methyl-2-[3-methyl-2-[[(E)-1-[4- (trifluoromethyl)-2-pyridyl]ethylideneamino]oxymethyl]phenyl]acetamide (this compound may be prepared from the methods described in WO 2022 / 033906), (2E)-2-[2-[[(E)-[3-(4-fluorophenyl)-1-methyl-prop-2- ynylidene]amino] oxymethyl]-3-methyl-phenyl]-2-methoxyimino-N-methyl-acetamide (this compound may be prepared from the methods described in WO 2021 / 249928), methyl (2E)-2-[2-[[(E)-[3-(4-fluorophenyl)-1- methyl-prop-2-ynylidene]amino]oxymethyl]-3-methyl-phenyl]-2-methoxyimino-acetate (this compound may be prepared from the methods described in WO 2021 / 249928), 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluoro- phenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile (this compound may be prepared from the methods described in WO 2016 / 156290), 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxy-propyl]imidazole-4- carbonitrile (this compound may be prepared from the methods described in WO 2016 / 156290), 2-[6-(4- bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1 ,2,4-triazol-1-yl)propan-2-ol (this compound may be prepared from the methods described in WO 2017 / 029179), 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1- (1 ,2,4-triazol-1-yl)propan-2-ol (this compound may be prepared from the methods described in WO 2017 / 029179), 5-[5-(difluoromethyl)-1 ,3,4-oxadiazol-2-yl]-N-[1-(2-fluorophenyl)ethyl]pyrimidin-2-amine (this compound may be prepared from the methods described in WO 2021 / 255093), 5-[5-(difluoromethyl)-1 ,3,4- oxadiazol-2-yl]-N-[1-(3,5-difluorophenyl)ethyl]pyrimidin-2-amine (this compound may be prepared from the methods described in WO 2021 / 255093), N-[1-(2-fluorophenyl)cyclopropyl]-5-[5-(trifluoromethyl)-1 ,3,4- oxadiazol-2-yl]pyrimidin-2-amine (this compound may be prepared from the methods described in WO 2021 / 255093), 5-[5-(difluoromethyl)-1 ,3,4-oxadiazol-2-yl]-N-[1-(2,6-difluorophenyl)ethyl]pyrimidin-2-amine (this compound may be prepared from the methods described in WO 2021 / 255093), 2-(difluoromethyl)-5-[2-[1- (2,6-difluorophenyl)cyclopropoxy]pyrimidin-5-yl]-1 ,3,4-oxadiazole (this compound may be prepared from the methods described in WO 2021 / 255093), 5-[5-(difluoromethyl)-1 ,3,4-oxadiazol-2-yl]-N-[1-(2- fluorophenyl)cyclopropyl]pyrimidin-2-amine (this compound may be prepared from the methods described in WO 2021 / 255093), 5-[(4-bromo-2-methyl-phenyl)methyl]-3-[3-(3-chloro-2-fluoro-phenoxy)-6-methyl-pyridazin- 4-yl]-5,6-dihydro-4H-1 ,2,4-oxadiazine (this compound may be prepared from the methods described in WO 2021 / 255070), 3-[3-(3-cyclopropyl-2-fluoro-phenoxy)-6-methyl-pyridazin-4-yl]-5-[(2,4-dimethylphenyl)methyl]- 5,6-dihydro-4H-1 ,2,4-oxadiazine (this compound may be prepared from the methods described in WO 2021 / 255070), N-(2,2,2-trifluoroethyl)-2-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]oxazole-4- carboxamide (this compound may be prepared from the methods described in WO 2022 / 133114), ethyl 1 -[[4- [5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl] phenoxy]methyl]pyrazole-4-carboxylate (this compound may be prepared from the methods described in WO 2022 / 1331 14), ethyl 1-[[4-[(Z)-2-ethoxy-3,3,3-trifluoro-prop-1- enoxy]phenyl]methyl]pyrazole-4-carboxylate (this compound may be prepared from the methods described in WO 2020 / 056090 and WO 2021 / 183707), ethyl 1-[[4-[[2-(trifluoromethyl)-1 ,3-dioxolan-2- yl]methoxy]phenyl]methyl]pyrazole-4-carboxylate (this compound may be prepared from the methods described in WO 2020 / 056090 and WO 2021 / 183707), methyl N-[[5-[4-(2,4-dimethylphenyl)triazol-2-yl]-2- methyl-phenyl]methyl]carbamate (this compound may be prepared from the methods described in WO 2020 / 097012), methyl N-[[5-[ 1 -(2,6-difluoro-4-isopropyl-phenyl)pyrazol-3-yl]-2-methyl-phenyl]rnethyl] carbamate (this compound may be prepared from the methods described in WO 2020 / 097012), methyl N-[[5- [1-(4-cyclopropyl-2,6-difluoro-phenyl)pyrazol-3-yl]-2-methyl-phenyl]methyl]- carbamate (this compound may be prepared from the methods described in WO 2020 / 097012), methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2- hydroxy-3-(1 ,2,4-triazol-1-yl)propanoate (this compound may be prepared from the methods described in WO 2019 / 093522), 4,4,5-trifluoro-3,3-dimethyl-1-(3-quinolyl)isoquinoline, 5-fluoro-3,3,4,4-tetramethyl-1-(3- quinolyl)isoquinoline, 2-methoxy-N-[methoxy-[5-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]-2-thienyl]methyl] acetamide (this compound may be prepared from the methods described in WO 2020 / 256113), N-[methoxy- [5-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]-2-thienyl]methyl]-2-methyl-propanamide (this compound may be prepared from the methods described in WO 2020 / 256113), N-[methoxy-[5-[5-(trifluoromethyl)-1 ,2,4-oxadiazol- 3-yl]-2-thienyl]methyl]butanamide (this compound may be prepared from the methods described in WO 2020 / 256113), 2-(difluoromethyl)-N-[(3R)-3-ethyl-1 ,1-dimethyl-indan-4-yl]pyridine-3-carboxamide (this compound may be prepared from the methods described in WO 2014 / 095675), 2-(difluoromethyl)-N-(3-ethyl- 1 ,1-dimethyl-indan-4-yl)pyridine-3-carboxamide (this compound may be prepared from the methods described in WO 2014 / 095675), 2-(difluoromethyl)-N-(1 ,1 ,3-trimethylindan-4-yl)pyridine-3-carboxamide, (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, (5S)-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, 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 (these compounds may be prepared from the methods described in W02020 / 127780, W02021 / 255070), 4-(2-methoxyethoxy)-2-[[4-[5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl]phenyl]methyl]pyridazin-3-one (this compound may be prepared from the methods described in WO2019 / 022061 , JP2021 181432), [4-(difluoromethoxy)phenyl]methyl 2,5-bis(1-ethoxyethyl)-4- [(E)-[1-ethoxyethyl(2-ethoxypropyl)amino]-methyleneamino]benzoate (this compound may be prepared from the methods described in WO2020 / 237131 and WO2024 / 233327), 2-[(2,6-difluoro-4-pyridyl)-(2- methylpropanoyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide, or the (R) or (S) enantiomer or mixtures thereof (this compound may be prepared from the methods described in WO2017207362A1 , WO2019105933A1 , W02020109511A1 , WO2021244952A1 ); 2-[(2,6-difluoro-4-pyridyl)- (tetrahydropyran-4-carbonyl)amino]-N-(2,2-dimethyl-cyclobutyl)-5-methyl-thiazole-4-carboxamide, or the (R) or (S) enantiomer or mixtures thereof (this compound may be prepared from the methods described in WO2017207362A1 , WO2019105933A1 , W02020109511A1 , WO2021244952A1 ); 2-[cyano-(2,6-difluoro-4- pyridyl)amino]-5-methyl-N-spiro[3.4]octan-3-yl-thiazole-4-carboxamide, or the (R) or (S) enantiomer or mixtures thereof (this compound may be prepared from the methods described in WO2017207362A1 , WO2019105933A1 , W02020109509A1 ); 2-[cyano-(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethylcyclobutyl)-5- methyl-thiazole-4-carboxamide, or the (R) or (S) enantiomer or mixtures thereof (this compound may be prepared from the methods described in WO2017207362A1 , WO2019105933A1 , W02020109509A1 ); 2-[(2,6- difluoro-4-pyridyl)-(2-methoxyacetyl) amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide, or the (R) or (S) enantiomer or mixtures thereof (this compound may be prepared from the methods described in WO2017207362A1 , WO2019105933A1 , W02020109511A1 , WO2021244952A1 ); 2-[acetyl-(2,6-difluoro-4- pyridyl)amino]-5-methyl-N-spiro[3.4]octan-3-yl-thiazole-4-carboxamide, or the (R) or (S) enantiomer or mixtures thereof (this compound may be prepared from the methods described in WO2017207362A1 , WO2019105933A1 , W02020109511 A1 , WO2021244952A1 ); N-methoxy-N-[[4-[5-(trifluoromethyl)-1 ,2,4- oxadiazol-3-yl]phenyl] methyl]cyclopropanecarboxamide (this compound may be prepared from the methods described in WO2017 / 055473); methyl (Z)-2-(5-cyclopentyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate (this compound may be prepared from the methods described in W02020 / 193387); methyl (Z)-2-(5-cyclohexyl-2- methyl-phenoxy)-3-methoxy-prop-2-enoate (this compound may be prepared from the methods described in W02020 / 193387); 2-[(2,6-difluoro-4-pyridyl)-(oxetane-3-carbonyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl- thiazole-4-carboxamide, or the (R) or (S) enantiomer or mixtures thereof (this compound may be prepared from the methods described in WO2017207362A1 , WO2019105933A1 , W02020109511A1 , WO2021244952A1 ); 2-[acetyl-(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide, or the (R) or (S) enantiomer or mixtures thereof (this compound may be prepared from the methods described in WO2017207362A1 , WO2019105933A1 , W02020109511A1 , WO2021244952A1 ); N,2-dimethoxy-N-[[4-[5- (trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, or the (R) or (S) enantiomer or mixtures thereof (this compound may be prepared from the methods described in WO2017 / 055473).

[0221] Most of the active ingredients described above are referred to hereinabove by a so-called "common name", the relevant "ISO common name" or another "common name" being used in individual cases. If the designation is not a "common name", the nature of the designation used instead is given in round brackets for the particular compound; in that case, the IUPAC name, the lUPAC / Chemical Abstracts name, a "chemical name", a "traditional name", a "compound name" or a "development code" is used or, if neither one of those designations nor a "common name" is used, an "alternative name" is employed. “CAS Reg. No” means the Chemical Abstracts Registry Number.

[0222] The active ingredient mixture of the compound selected from compounds of formula (I), or compounds selected from compounds listed in Tables C-1 to C-56, or compounds listed in Table P (below), is preferably in a mixing ratio of from 100:1 to 1 :100, especially from 50:1 to 1 :50, more especially in a ratio of from 20:1 to 1 :20, even more especially from 10:1 to 1 :10, and still more especially from 5:1 to 1 :5 Those mixing ratios are by weight.

[0223] The mixtures as described above can be used in a method for controlling pests, which comprises applying a composition comprising a mixture as described above to the pests or their environment, with the exception of a method for treatment of the human or animal body by surgery or therapy and diagnostic methods practised on the human or animal body.

[0224] The mixtures comprising a compound selected from compounds of formula (I), or compounds selected from compounds listed in Tables C-1 to C-56, or compounds listed in Table P (below), and one or more active ingredients as described above can be applied, for example, in a single “ready-mix” form, in a combined spray mixture composed from separate formulations of the single active ingredient components, such as a “tank-mix”, and in a combined use of the single active ingredients when applied in a sequential manner, i.e. one after the other with a reasonably short period, such as a few hours or days. The order of applying a compound selected from compounds of formula (I), or compounds selected from compounds listed in Tables C-1 to C-56, or compounds listed in Table P (below), and the active ingredient(s) as described above, is not essential for working the present invention.

[0225] The compositions according to the invention can also comprise further solid or liquid auxiliaries, such as stabilizers, for example unepoxidized or epoxidized vegetable oils (for example epoxidized coconut oil, rapeseed oil or soya oil), antifoams, for example silicone oil, preservatives, viscosity regulators, binders and / or tackifiers, fertilizers or other active ingredients for achieving specific effects, for example bactericides, fungicides, nematocides, plant activators, molluscicides, or herbicides.

[0226] The compositions according to the invention are prepared in a manner known per se, in the absence of auxiliaries for example by grinding, screening and / or compressing a solid active ingredient and in the presence of at least one auxiliary for example by intimately mixing and / or grinding the active ingredient with the auxiliary (auxiliaries). These processes for the preparation of the compositions and the use of the compounds (I) for the preparation of these compositions are also a subject of the invention.

[0227] Another aspect of the invention is related to the use of a compound of formula (I) according to the invention or of a preferred individual compound as defined herein, of a composition comprising at least one compound of formula (I) or at least one preferred individual compound as defined herein, or of a fungicidal or insecticidal mixture comprising at least one compound of formula (I) or at least one preferred individual compound as defined herein, in admixture with other fungicides or insecticides as described above, for controlling or preventing infestation of plants, e.g., useful plants such as crop plants, propagation material thereof, e.g., seeds, harvested crops, e.g., harvested food crops, or non-living materials by insects, or by phytopathogenic microorganisms, preferably fungal organisms.

[0228] A further aspect of invention is related to a method of controlling or preventing an infestation of plants, e.g., useful plants such as crop plants, propagation material thereof, e.g., seeds, harvested crops, e.g., harvested food crops, or of non-living materials by phytopathogenic or spoilage microorganisms or organisms potentially harmful to man, especially fungal organisms, which comprises the application of a compound of formula (I) according to the invention or of a preferred individual compound as defined herein as active ingredient to the plants, to parts of the plants or to the locus thereof, to the propagation material thereof, or to any part of the non-living materials.

[0229] Controlling or preventing means reducing infestation by insects, or by phytopathogenic or spoilage microorganisms, or organisms potentially harmful to man, especially fungal organisms, to such a level that an improvement is demonstrated.

[0230] A preferred method of controlling or preventing an infestation of crop plants by phytopathogenic microorganisms, especially fungal organisms, or insects which comprises the application of a compound of formula (I) according to the invention, or an agrochemical composition which contains at least one compound of formula (I), is foliar application. The frequency of application and the rate of application will depend on the risk of infestation by the corresponding pathogen or insect. However, the compounds of formula (I) according to the invention can also penetrate the plant through the roots via the soil (systemic action) by drenching the locus of the plant with a liquid formulation, or by applying the compounds in solid form to the soil, e.g., in granular form (soil application). In crops of water rice such granulates can be applied to the flooded rice field. The compounds of formula (I) may also be applied to seeds (coating) by impregnating the seeds or tubers either with a liquid formulation of the fungicide or coating them with a solid formulation.

[0231] A formulation, e.g., a composition containing the compound of formula (I) according to the invention and, if desired, a solid or liquid adjuvant or monomers for encapsulating the compound of formula (I), may be prepared in a known manner, typically by intimately mixing and / or grinding the compound with extenders, for example solvents, solid carriers and, optionally, surface active compounds (surfactants).

[0232] Advantageous rates of application are normally from 5 g to 2 kg of active ingredient (a.i.) per hectare (ha), preferably from 10 g to 1 kg a.i. / ha, most preferably from 20 g to 600 g a.i. / ha. When used as seed drenching agent, convenient dosages are from 10 mg to 1 g of active substance per kg of seeds.

[0233] The term “g a.i. / ha” as used herein refer to the application rate given in gram [g] of active ingredient [a.i.] per unit of surface [ha]. The unit hectare (symbol ha) is the metric unit of area that equals a square with 100 m side (1 hm2) or 10,000 square meters. Hectare is a commonly used unit of area in the metric system.

[0234] When the combinations of the present invention are used for treating seed, rates of 0.001 to 50 g of a compound of formula (I) per kg of seed, preferably from 0.01 to 10g per kg of seed are generally sufficient.

[0235] Suitably, a composition comprising a compound of formula (I) according to the present invention is applied either preventative, meaning prior to disease development or curative, meaning after disease development.

[0236] The compositions of the invention may be employed in any conventional form, for example in the form of a twin pack, a powder for dry seed treatment (DS), an emulsion for seed treatment (ES), a flowable concentrate for seed treatment (FS), a solution for seed treatment (LS), a water dispersible powder for seed treatment (WS), a capsule suspension for seed treatment (CF), a gel for seed treatment (GF), an emulsion concentrate (EC), a suspension concentrate (SC), a suspo-emulsion (SE), a capsule suspension (CS), a water dispersible granule (WG), an emulsifiable granule (EG), an emulsion, water in oil (EG), an emulsion, oil in water (EW), a microemulsion (ME), an oil dispersion (OD), an oil miscible flowable (OF), an oil miscible liquid (OL), a soluble concentrate (SL), an ultra-low volume suspension (SU), an ultra-low volume liquid (UL), a technical concentrate (TK), a dispersible concentrate (DC), a wettable powder (WP) or any technically feasible formulation in combination with agriculturally acceptable adjuvants.

[0237] Such compositions may be produced in conventional manner, e.g., by mixing the active ingredients with appropriate formulation inerts (diluents, solvents, fillers, and optionally other formulating ingredients such as surfactants, biocides, anti-freeze, stickers, thickeners, and compounds that provide adjuvancy effects). Also, conventional slow-release formulations may be employed where long lasting efficacy is intended. Particularly formulations to be applied in spraying forms, such as water dispersible concentrates (e.g., EC, SC, DC, OD, SE, EW, EG and the like), wettable powders and granules, may contain surfactants such as wetting and dispersing agents and other compounds that provide adjuvancy effects, e.g., the condensation product of formaldehyde with naphthalene sulfonate, an alkyl aryl sulfonate, a lignin sulfonate, a fatty alkyl sulphate, and ethoxylated alkylphenol and an ethoxylated fatty alcohol.

[0238] A seed dressing formulation is applied in a manner known per se to the seeds employing the combination of the invention and a diluent in suitable seed dressing formulation form, e.g., as an aqueous suspension or in a dry powder form having good adherence to the seeds. Such seed dressing formulations are known in the art. Seed dressing formulations may contain the single active ingredients or the combination of active ingredients in encapsulated form, e.g., as slow-release capsules or microcapsules.

[0239] In general, the formulations include from 0.01 to 90% by weight of active agent, from 0 to 20% agriculturally acceptable surfactant and 10 to 99.99% solid or liquid formulation inerts, and adjuvant(s), the active agent consisting of at least the compound of formula (I) according to the invention optionally together with other active agents, particularly microbiocides or conservatives or the like. Concentrated forms of compositions generally contain in between about 2 to 80%, preferably between about 5 to 70% by weight of active agent. Application forms of formulation may for example contain from 0.01 to 20% by weight, preferably from 0.01 to 5% by weight of active agent. Whereas commercial products will preferably be formulated as concentrates, the end user will normally employ diluted formulations.

[0240] Whereas it is preferred to formulate commercial products as concentrates, the end user will normally use dilute formulations.

[0241] The rates of application vary within wide limits and depend on the nature of the soil, the method of application, the crop plant, the pest to be controlled, the prevailing climatic conditions, and other factors governed by the method of application, the time of application and the target crop. As a general guideline, compounds may be applied at a rate of from 1 to 2000 l / ha, especially from 10 to 1000 l / ha.

[0242] Preferred formulations can have the following compositions (weight %)

[0243] Emulsifiable concentrates: active ingredient: 1 to 95 %, preferably 60 to 90 % surface-active agent: 1 to 30 %, preferably 5 to 20 % liquid carrier: 1 to 80 %, preferably 1 to 35 %

[0244] Dusts: active ingredient: 0.1 to 10 %, preferably 0.1 to 5 % solid carrier: 99.9 to 90 %, preferably 99.9 to 99 %

[0245] Suspension concentrates: active ingredient: 5 to 75 %, preferably 10 to 50 % water: 94 to 24 %, preferably 88 to 30 % surface-active agent: 1 to 40 %, preferably 2 to 30 %

[0246] Wettable powders: active ingredient: 0.5 to 90 %, preferably 1 to 80 % surface-active agent: 0.5 to 20 %, preferably 1 to 15 % solid carrier: 5 to 95 %, preferably 15 to 90 %

[0247] Granules: active ingredient: 0.1 to 30 %, preferably 0.1 to 15 % solid carrier: 99.5 to 70 %, preferably 97 to 85 %

[0248] The disclosure in the present application makes available each and every combination of embodiments disclosed herein.

[0249] The compounds according to the following Tables C-1 to C-56 may be prepared according to the methods described above. The examples which follow are intended to illustrate the invention and show preferred compounds of formula (I). In any of Tables C-1 to C-56 below, the presence of one or more possible asymmetric carbon atoms in a compound of formula (I) according to the invention means that the compounds may occur in chiral isomeric forms, i.e., enantiomeric or diastereomeric forms.

[0250] Table A: This table discloses 34 substituent definitions Z1of compounds of the formula (I) according to the invention: wherein Z1according to compounds of formula (I) of the invention is, are as defined below:

[0251] Table B: This table discloses 28 substituent definitions Q of compounds of the formula (I) according to the invention: wherein Q according to compounds of formula (I) of the invention is, are as defined below:

[0252] The following compounds are thus specifically described in Tables C-1 to C-56 with the substituents for formula (I)

[0253] Table C-1 : This table provides 34 compounds (C-1 .01 ) to (C-1 .34) of formula (I), wherein R1, R2, and R3are H; B1and B2are CH, Q is Q-1 (Table B), and Z1substituents are as defined in Table A. For example, compound (C-1 .01 ) has the following structure:

[0254] (Compound C-1 .01 ) Table C-2 This table provides 34 compounds (C-2.01 ) to (C-2.34) of formula (I), wherein R1R2, and R3are H;

[0255] B1and B2are CH, Q is Q-2 (Table B), and Z1substituents are as defined in Table A.

[0256] Table C-3 This table provides 34 compounds (C-3.01 ) to (C-3.34) of formula (I), wherein R1R2, and R3are H;

[0257] B1and B2are CH; Q is Q-3 (Table B), and Z1substituents are as defined in Table A.

[0258] Table C-4: This table provides 34 compounds (C-4.01 ) to (C-4.34) of formula (I), wherein R1, R2, and R3are H;

[0259] B1and B2are CH, Q is Q-4 (Table B), and Z1substituents are as defined in Table A.

[0260] Table C-5: This table provides 34 compounds (C-5.01 ) to (C-5.34) of formula (I), wherein R1, R2, and R3are H;

[0261] B1and B2are CH, Q is Q-5 (Table B), and Z1substituents are as defined in Table A.

[0262] Table C-6: This table provides 34 compounds (C-6.01 ) to (C6.34) of formula (I), wherein R1, R2, and R3are H;

[0263] B1and B2are CH, Q is Q-6 (Table B), and Z1substituents are as defined in Table A.

[0264] Table C-7: This table provides 34 compounds (C-7.01 ) to (C-7.34) of formula (I), wherein R1, R2, and R3are H;

[0265] B1and B2are CH, Q is Q-7 (Table B), and Z1substituents are as defined in Table A.

[0266] Table C-8: This table provides 34 compounds (C-8.01 ) to (C-8.34) of formula (I), wherein R1, R2, and R3are H;

[0267] B1and B2are CH, Q is Q-8 (Table B), and Z1substituents are as defined in Table A.

[0268] Table C-9: This table provides 34 compounds (C-9.01 ) to (C-9.34) of formula (I), wherein R1, R2, and R3are H;

[0269] B1and B2are CH, Q is Q-9 (Table B), and Z1substituents are as defined in Table A.

[0270] Table C-10: This table provides 34 compounds (C-10.01 ) to (C-10.34) of formula (I), wherein R1, R2, and R3are H; B1and B2are CH, Q is Q-10 (Table B), and Z1substituents are as defined in Table A.

[0271] Table C-11 : This table provides 34 compounds (C-11 .01 ) to (C-11.34) of formula (I), wherein R1, R2, and R3are H; B1and B2are CH, Q is Q-11 (Table B), and Z1substituents are as defined in Table A.

[0272] Table C-12: This table provides 34 compounds (C-12.01 ) to (C-12.34) of formula (I), wherein R1, R2, and R3are H; B1and B2are CH, Q is Q-12 (Table B), and Z1substituents are as defined in Table A.

[0273] Table C-13: This table provides 34 compounds (C-13.01 ) to (C-13.34) of formula (I), wherein R1, R2, and R3are H; B1and B2are CH, Q is Q-13 (Table B), and Z1substituents are as defined in Table A.

[0274] Table C-14: This table provides 34 compounds (C-14.01 ) to (C-14.34) of formula (I), wherein R1, R2, and R3are H; B1and B2are CH, Q is Q-14 (Table B), and Z1substituents are as defined in Table A.

[0275] Table C-15: This table provides 34 compounds (C-15.01 ) to (C-15.34) of formula (I), wherein R1, R2, and R3are H; B1and B2are CH, Q is Q-15 (Table B), and Z1substituents are as defined in Table A.

[0276] Table C-16: This table provides 34 compounds (C-16.01 ) to (C-16.34) of formula (I), wherein R1, R2, and R3are H; B1and B2are CH, Q is Q-16 (Table B), and Z1substituents are as defined in Table A.

[0277] Table C-17: This table provides 34 compounds (C-17.01 ) to (C-17.34) of formula (I), wherein R1, R2, and R3are H; B1and B2are CH, Q is Q-17 (Table B), and Z1substituents are as defined in Table A. Table C-18 This table provides 34 compounds (C-18.01 ) to (C-18.34) of formula (I), wherein R1R2, and R3are H; B1and B2are CH, Q is Q-18 (Table B), and Z1substituents are as defined in Table A.

[0278] Table C-19 This table provides 34 compounds (C-19.01 ) to (C-19.34) of formula (I), wherein R1R2, and R3are H; B1and B2are CH, Q is Q-19 (Table B), and Z1substituents are as defined in Table A. For example, compound C-19.22 has the following structure:

[0279] (Compound C-19.22)

[0280] Table C-20: This table provides 34 compounds (C-20.01 ) to (C-20.34) of formula (I), wherein R1, R2, and R3are H; B1and B2are CH, Q is Q-20 (Table B), and Z1substituents are as defined in Table A.

[0281] Table C-21 : This table provides 34 compounds (C-21 .01 ) to (C-21.34) of formula (I), wherein R1, R2, and R3are H; B1and B2are CH, Q is Q-21 (Table B), and Z1substituents are as defined in Table A.

[0282] Table C-22: This table provides 34 compounds (C-22.01 ) to (C-22.34) of formula (I), wherein R1, R2, and R3are H; B1and B2are CH, Q is Q-22 (Table B), and Z1substituents are as defined in Table A.

[0283] Table C-23: This table provides 34 compounds (C-23.01 ) to (C-23.34) of formula (I), wherein R1, R2, and R3are H; B1and B2are CH, Q is Q-23 (Table B), and Z1substituents are as defined in Table A.

[0284] Table C-24: This table provides 34 compounds (C-24.01 ) to (C-24.34) of formula (I), wherein R1, R2, and R3are H; B1and B2are CH, Q is Q-24 (Table B), and Z1substituents are as defined in Table A.

[0285] Table C-25: This table provides 34 compounds (C-25.01 ) to (C-25.34) of formula (I), wherein R1, R2, and R3are H; B1and B2are CH, Q is Q-25 (Table B), and Z1substituents are as defined in Table A.

[0286] Table C-26: This table provides 34 compounds (C-26.01 ) to (C-26.34) of formula (I), wherein R1, R2, and R3are H; B1and B2are CH, Q is Q-26 (Table B), and Z1substituents are as defined in Table A.

[0287] Table C-27: This table provides 34 compounds (C-27.01 ) to (C-27.34) of formula (I), wherein R1, R2, and R3are H; B1and B2are CH, Q is Q-27 (Table B), and Z1substituents are as defined in Table A.

[0288] Table C-28: This table provides 34 compounds (C-28.01 ) to (C-28.34) of formula (I), wherein R1, R2, and R3are H; B1and B2are CH, Q is Q-28 (Table B), and Z1substituents are as defined in Table A.

[0289] Table C-29: This table provides 34 compounds (C-29.01 ) to (C-29.34) of formula (I), wherein R1, R2, and R3are H; B1is CH, B2is C-CN, Q is Q-19 (Table B), and Z1substituents are as defined in Table A.

[0290] Table C-30: This table provides 34 compounds (C-30.01 ) to (C-30.34) of formula (I), wherein R1, R2, and R3are H; B1is CH, B2is C-CN, Q is Q-22 (Table B), and Z1substituents are as defined in Table A. For example, compound C-30.17 has the following structure:

[0291] (Compound C-30.17)

[0292] Table C-31 : This table provides 34 compounds (C-31 .01 ) to (C-31.34) of formula (I), wherein R1, R2, and R3are H; B1is CH, B2is C-CN, Q is Q-13 (Table B), and Z1substituents are as defined in Table A.

[0293] Table C-32: This table provides 34 compounds (C-32.01 ) to (C-32.34) of formula (I), wherein R1, R2, and R3are H; B1is CH, B2is C-CO2CH3, Q is Q-19 (Table B), and Z1substituents are as defined in Table A.

[0294] Table C-33: This table provides 34 compounds (C-33.01 ) to (C-33.34) of formula (I), wherein R1, R2, and R3are H; B1is CH, B2is C-CO2CH3, Q is Q-22 (Table B), and Z1substituents are as defined in Table A.

[0295] Table C-34: This table provides 34 compounds (C-34.01 ) to (C-34.34) of formula (I), wherein R1, R2, and R3are H; B1is CH, B2is C-CO2CH3, Q is Q-13 (Table B), and Z1substituents are as defined in Table A.

[0296] Table C-35: This table provides 34 compounds (C-35.01 ) to (C-35.34) of formula (I), wherein R1, R2, and R3are H; B1is CH, B2is C-CO2CH2CH3, Q is Q-19 (Table B), and Z1substituents are as defined in Table A.

[0297] Table C-36: This table provides 34 compounds (C-36.01 ) to (C-36.34) of formula (I), wherein R1, R2, and R3are H; B1is CH, B2is C-CO2CH2CH3, Q is Q-22 (Table B), and Z1substituents are as defined in Table A.

[0298] Table C-37: This table provides 34 compounds (C-37.01 ) to (C-37.34) of formula (I), wherein R1, R2, and R3are H; B1is CH, B2is C-CO2CH2CH3, Q is Q-13 (Table B), and Z1substituents are as defined in Table A.

[0299] Table C-38: This table provides 34 compounds (C-38.01 ) to (C-38.34) of formula (I), wherein R1, R2, and R3are H; B1is CH, B2is C-Br, Q is Q-19 (Table B), and Z1substituents are as defined in Table A.

[0300] Table C-39: This table provides 34 compounds (C-39.01 ) to (C-39.34) of formula (I), wherein R1, R2, and R3are H; B1is CH, B2is C-Br, Q is Q-22 (Table B), and Z1substituents are as defined in Table A.

[0301] Table C-40: This table provides 34 compounds (C-40.01 ) to (C-40.34) of formula (I), wherein R1, R2, and R3are H; B1is CH, B2is C-Br, Q is Q-13 (Table B), and Z1substituents are as defined in Table A. For example, compound C-40.13 has the following structure:

[0302] (Compound C-40.13) Table C-41 This table provides 34 compounds (C-41 .01 ) to (C-41 .34) of formula (I), wherein R1, R2, and R3are H; B1is C-F, B2is C-CN, Q is Q-19 (Table B), and Z1substituents are as defined in Table A. For example, compound C-41 .01 has the following structure:

[0303] (Compound C-41 .01 )

[0304] Table C-42: This table provides 34 compounds (C-42.01 ) to (C-42.34) of formula (I), wherein R1, R2, and R3are H; B1is C-F, B2is C-CN, Q is Q-22 (Table B), and Z1substituents are as defined in Table A.

[0305] Table C-43: This table provides 34 compounds (C-43.01 ) to (C-43.34) of formula (I), wherein R1, R2, and R3are H; B1is C-F, B2is C-CN, Q is Q-13 (Table B), and Z1substituents are as defined in Table A.

[0306] Table C-44: This table provides 34 compounds (C-44.01 ) to (C-44.34) of formula (I), wherein R1, R2, and R3are H; B1is C-OCH3, B2is C-CN, Q is Q-19 (Table B), and Z1substituents are as defined in Table A.

[0307] Table C-45 This table provides 34 compounds (C-45.01 ) to (C-45.34) of formula (I), wherein R1R2, and R3are H; B1is C-OCH3, B2is C-CN, Q is Q-22 (Table B), and Z1substituents are as defined in Table A.

[0308] Table C-46 This table provides 34 compounds (C-46.01 ) to (C-46.34) of formula (I), wherein R1R2, and R3are H; B1is C-OCH3, B2is C-CN, Q is Q-13 (Table B), and Z1substituents are as defined in Table A.

[0309] Table C-47 This table provides 34 compounds (C-47.01 ) to (C-47.34) of formula (I), wherein R1 are H; B1is C-OCH3, B2is C-CN, Q is Q-19 (Table B), and Z1substituents are as defined in Table A.

[0310] Table C-48: This table provides 28 compounds (C-48.01 ) to (C-48.28) of formula (I), wherein R1, R2, and R3are H; B1is CH, B2is N, Z1is pentyl, and Q substituents are as defined in Table B. For example, compound C- 48.15 has the following structure:

[0311] (Compound C-48.15)

[0312] Table C-49: This table provides 28 compounds (C-49.01 ) to (C-49.28) of formula (I), wherein R1, R2, and R3are H; B1is N, B2is C-H, Z1is pentyl, and Q substituents are as defined in Table B.

[0313] Table C-50 This table provides 28 compounds (C-50.01 ) to (C-50.28) of formula (I), wherein R1R2, are H, R3is methyl, B1is CH, B2is C-CN, Z1is pentyl, and Q substituents are as defined in Table B. For example, compound C-50.06 has the following structure:

[0314] (Compound C-50.06)

[0315] Table C-51 : This table provides 34 compounds (C-51 .01 ) to (C-51.34) of formula (I), wherein R1, R2, and R3are H; B1is CH, B2is C-CN, Q is Q-18 (Table B), and Z1substituents are as defined in Table A.

[0316] Table C-52: This table provides 34 compounds (C-52.01 ) to (C-52.34) of formula (I), wherein R1, R2, and R3are H; B1is CH, B2is C-CO2CH3, Q is Q-18 (Table B), and Z1substituents are as defined in Table A.

[0317] Table C-53: This table provides 34 compounds (C-53.01 ) to (C-53.34) of formula (I), wherein R1, R2, and R3are H; B1is CH, B2is C-CO2CH2CH3, Q is Q-18 (Table B), and Z1substituents are as defined in Table A.

[0318] Table C-54: This table provides 34 compounds (C-54.01 ) to (C-54.34) of formula (I), wherein R1, R2, and R3are H; B1is CH, B2is C-Br, Q is Q-18 (Table B), and Z1substituents are as defined in Table A.

[0319] Table C-55: This table provides 34 compounds (C-55.01 ) to (C-55.34) of formula (I), wherein R1, R2, and R3are H; B1is C-F, B2is C-CN, Q is Q-18 (Table B), and Z1substituents are as defined in Table A. For example, compound C-54.01 has the following structure

[0320] Table C-56 This table provides 34 compounds (C-56.01 ) to (C-56.34) of formula (I), wherein R1R2, and R3are H; B1is C-OCH3, B2is C-CN, Q is Q-18 (Table B), and Z1substituents are as defined in Table A.

[0321] EXAMPLES

[0322] The Examples which follow serve to illustrate the invention and are not meant in any way to limit the invention.

[0323] The compounds of the invention can be distinguished from known compounds by virtue of greater efficacy at low application rates, which can be verified by a person skilled in the art using the experimental procedures outlined in the Examples, using lower application rates if necessary, for example 60 ppm, 20 ppm or 2 ppm.

[0324] Compounds of formula (I) may possess any number of benefits including, inter alia, advantageous levels of biological activity for protecting plants against diseases that are caused by fungi or superior properties for use as agrochemical active ingredients (for example, greater biological activity, an advantageous spectrum of activity, an increased safety profile (including improved crop tolerance), improved physico-chemical properties, or increased biodegradability). FORMULATION EXAMPLES

[0325] Wettable powders a) b) c) active ingredients 25 % 50 % 75 % sodium lignosulfonate 5 % 5 % - sodium lauryl sulfate 3 % - 5 % sodium diisobutylnaphthalenesulfonate 6 % 10 % phenol polyethylene glycol ether (7-8 mol of ethylene oxide) 2 % highly dispersed silicic acid 5 % 10 % 10 %

[0326] Kaolin 62 % 27 % -

[0327] The combination is thoroughly mixed with the adjuvants, and the mixture is thoroughly ground in a suitable mill, affording wettable powders that can be diluted with water to give suspensions of the desired concentration.

[0328] Powders for dry seed treatment a) b) c) active ingredients 25 % 50 % 75 % light mineral oil 5 % 5 % 5 % highly dispersed silicic acid 5 % 5 % Kaolin 65 % 40 % -

[0329] Talcum 20 %

[0330] The combination is thoroughly mixed with the adjuvants, and the mixture is thoroughly ground in a suitable mill, affording powders that can be used directly for seed treatment.

[0331] Emulsifiable concentrate active ingredients 10 % octylphenol polyethylene glycol ether (4-5 mol of ethylene oxide) 3 % calcium dodecylbenzene sulfonate 3 % castor oil polyglycol ether (35 mol of ethylene oxide) 4 %

[0332] Cyclohexanone 30 % xylene mixture 50 %

[0333] Emulsions of any required dilution, which can be used in plant protection, can be obtained from this concentrate by dilution with water.

[0334] Dusts a) b) c)

[0335] Active ingredients 5 % 6 % 4 %

[0336] Talcum 95 % -

[0337] Kaolin 94 % - mineral filler 96 %

[0338] Ready-for-use dusts are obtained by mixing the combination with the carrier and grinding the mixture in a suitable mill. Such dusts can also be used for dry dressings for seed. Extruder granules

[0339] Active ingredients 15 % sodium lignosulfonate 2 % carboxymethylcellulose 1 %

[0340] Kaolin 82 %

[0341] The combination is mixed and ground with the adjuvants, and the mixture is moistened with water. The mixture is extruded and then dried in a stream of air.

[0342] Coated granules

[0343] Active ingredients 8% polyethylene glycol (mol. wt. 200) 3 %

[0344] Kaolin 89 %

[0345] The finely ground combination is uniformly applied, in a mixer, to the kaolin moistened with polyethylene glycol.

[0346] Non-dusty coated granules are obtained in this manner.

[0347] Suspension concentrates active ingredients 40 % propylene glycol 10 % nonylphenol polyethylene glycol ether (15 mol of ethylene oxide) 6 %

[0348] Sodium lignosulfonate 10 % carboxymethylcellulose 1 % silicone oil (in the form of a 75 % emulsion in water) 1 %

[0349] Water 32 %

[0350] The finely ground combination is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. Using such dilutions, living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion.

[0351] Flowable concentrate for seed treatment active ingredients 40 % propylene glycol 5 % copolymer butanol PO / EO 2 %

[0352] Tristyrenephenole with 10-20 moles EO 2 %

[0353] 1 ,2-benzisothiazolin-3-one (in the form of a 20% solution in water) 0.5 % monoazo-pigment calcium salt 5 %

[0354] Silicone oil (in the form of a 75 % emulsion in water) 0.2 %

[0355] Water 45.3 %

[0356] The finely ground combination is intimately mixed with the adjuvants, giving a flowable concentrate from which solutions of any desired dilution can be obtained by dilution with water, that can be used directly for seed treatment. Using such dilutions, living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion.

[0357] Slow-Release Capsule Suspension

[0358] 28 parts of the combination are mixed with 2 parts of an aromatic solvent and 7 parts of toluene diisocyanate / polymethylene-polyphenylisocyanate-mixture (8:1). This mixture is emulsified in a mixture of 1 .2 parts of polyvinylalcohol, 0.05 parts of a defoamer and 51.6 parts of water until the desired particle size is achieved. To this emulsion a mixture of 2.8 parts 1 ,6-diaminohexane in 5.3 parts of water is added. The mixture is agitated until the polymerization reaction is completed. The obtained capsule suspension is stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersing agent. The capsule suspension formulation contains 28% of the active ingredients. The medium capsule diameter is 8-15 microns. The resulting formulation is applied to seeds as an aqueous suspension in an apparatus suitable for that purpose.

[0359] Formulation types include an emulsion concentrate (EC), a suspension concentrate (SC), a suspo-emulsion (SE), a capsule suspension (CS), a water dispersible granule (WG), an emulsifiable granule (EG), an emulsion, water in oil (EG), an emulsion, oil in water (EW), a micro-emulsion (ME), an oil dispersion (OD), an oil miscible flowable (OF), an oil miscible liquid (OL), a soluble concentrate (SL), an ultra-low volume suspension (SU), an ultra-low volume liquid (UL), a technical concentrate (TK), a dispersible concentrate (DC), a wettable powder (WP), a soluble granule (SG) or any technically feasible formulation in combination with agriculturally acceptable adjuvants.

[0360] ABBREVIATIONS

[0361] CDCI3 deuterated chloroform

[0362] DABCO 1 ,4-diazabicyclo[2.2.2]octane, also known as triethylenediamine or TEDA

[0363] DMF dimethylformamide

[0364] DMSO dimethyl sulfoxide

[0365] DMSO-d6 deuterated Dimethyl sulfoxide

[0366] EtOAc ethylacetate

[0367] HCI hydrochloric acid h / hrs hour / hours

[0368] LC-MS Liquid Chromatography Mass Spectrometry (LC-MS, LCMS or LC / MS)

[0369] MgSO4 magnesium sulphate

[0370] Na2SO4 sodium sulphate

[0371] NaHCOs sodium hydrogen carbonate rh relative humidity rt room temperature

[0372] Rt retention time sat. saturated ssp. subspecies

[0373] THF tetrahydrofuran PREPARATION EXAMPLES

[0374] The compounds of formula (I) according to the invention may be prepared using the synthetic techniques described both above and below.

[0375] Throughout this description, temperatures are given in degrees Celsius and “m.p.” means melting point. LC / MS means Liquid Chromatography Mass Spectroscopy and the description of the apparatus, and the methods is as follows.

[0376] 1H NMR and19F NMR measurements were recorded on a Bruker 400MHz spectrometer, chemical shifts are given in ppm relevant to a TMS (1H) and CFCI3 (19F) standard. Spectra measured in deuterated solvents as indicated. The characteristic LC-MS values obtained for each compound were the retention time (“Rt”, recorded in minutes) and the measured molecular ion [M+H]+or (M-H)-. The following LC-MS methods were used for the analysis of the compounds:

[0377] Method A: Spectra were recorded on a Mass Spectrometer from Waters Corporation (SQD, SQDII or QDA Single quadrupole mass spectrometer) equipped with an electrospray source (Polarity: positive and negative ions), Capillary: 0.8-3.00 kV, Cone: 5-30 V, Source Temperature: 120-150°C, Desolvation Temperature: 350- 600°C, Cone Gas Flow: 50-150 l / h, Desolvation Gas Flow: 650-1000 l / h, Mass range: 110 to 950 Da and an Acquity UPLC from Waters Corporation: Binary pump, heated column compartment, diode-array detector and ELSD. Column: Waters UPLC HSS T3, 1 .8 pm, 30 x 2.1 mm, Temp: 60 °C, DAD Wavelength range (nm): 210 to 400, Runtime: 1 .5 min; Solvents: A = water + 5% MeOH + 0.05 % HCOOH, B= Acetonitrile + 0.05 % HCOOH; Flow (ml / min) 0.85, Gradient: 10% B isocratic for 0.2 min, then 10-100% B in 1.0 min, 100% B isocratic for 0.2min, 100-10% B in 0.05min, 10% B isocratic for 0.05 min.

[0378] Example P1 : Preparation of 4-(4,5-dimethylpyrazol-1 -yl)-A / -pentyl-quinoline-2-carboxamide (Compound P-1 , Table P)

[0379] (Compound P-1 , Table P)

[0380] Step 1 : Preparation of methyl 4-(2-tert-butoxycarbonylhydrazino) quinoline-2-carboxylate

[0381] To a solution of methyl 4-bromoquinoline-2-carboxylate (500 mg, 1.87 mmol) in toluene (9 mL) were added terf-butyl A / -amino carbamate (0.304 g, 2.25 mmol), and Pd2(dba)3 (88 mg, 0.093 mmol). To this solution was added 2, 2'-bis(diphenylphosphino)-1 ,1 '-binaphthyl (BINAP, 84 mg, 0.131 mmol) and caesium carbonate (858 mg, 2.63 mmol), under argon. The resulting reaction mixture was stirred at 1 10°C under argon monitoring by LCMS. Upon reaction completion, the reaction mixture was diluted with H2O and extracted with EtOAc (x3). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude solid was triturated with EtOAc and pentane (1 :1 ) and the solid filtered off to obtain the title compound as a white solid. LCMS: (Method A); Rt = 0.69 min, m / z = 319 [M+H]+;1H NMR (400 MHz, CDCI3) 6 = 8.27 - 8.13 (m, 1 H), 7.92 - 7.82 (m, 1 H), 7.72 - 7.63 (m, 1 H), 7.58 (s, 1 H), 7.54 - 7.42 (m, 1 H), 7.28 - 7.14 (m, 1 H), 7.04 - 6.57 (m, 1 H), 4.17 - 4.02 (m, 3H), 1.70 - 1.45 (m, 9H)

[0382] Step 2: Preparation of methyl 4-hvdrazinoquinoline-2-carboxylate

[0383] A sample of methyl 4-(2-tert-butoxycarbonylhydrazino) quinoline-2-carboxylate (310 mg, 0.976 mmol) was suspended in HCI in / so-PrOH (5.5 mol / L, 2.44 mL) and stirred at 45°C monitoring by LCMS. After reaction completion, the reaction mixture concentrated in vacuo to yield the title compound as the HCI salt. LCMS: (Method A); Rt = 0.24 min, m / z = 218 [M+H]+;1H NMR (400 MHz, d6-DMSO) 5 = 8.61 - 8.51 (m, 1 H), 8.22 (d, J = 8.0 Hz, 1 H), 8.01 - 7.88 (m, 1 H), 7.74 - 7.58 (m, 2H), 6.76 - 6.27 (m, 2H), 4.06 (s, 3H)

[0384] Step 3: Preparation of (E)-l-(dimethylamino) pent-1 -en-3-one and (E)-4-(dimethylamino)-3-methyl-but-3-en-2- one

[0385] Dimethylformamid-dimethylacetal (2.23 mL 16.78 mmol) was added to 2-butanone (16.7 mmol) and the reaction mixture was stirred at 80°C for 20 hr. The reaction mixture was allowed to cool to rt, concentrated in vacuo to afford a 1 :1 mixture of the title compounds, which were used without further purification in the next step. LCMS: (Method A); Rt = 0.43 min, m / z = 128 [M+H]+, both isomers

[0386] Step 4: Preparation of methyl 4-(4,5-dimethylpyrazol-1-yl) quinoline-2-carboxylate

[0387] A sample of methyl 4-hydrazinoquinoline-2-carboxylate HCI salt (160 mg, 0.64 mmol) and (E)-1- (dimethylamino) pent-1 -en-3-one / (E)-4-(dimethylamino)-3-methyl-but-3-en-2-one mixture (120 mg, 0.64 mmol) were dissolved in ethanol (4 mL) and treated with cone. HCI (0.053 mL, 0.54 mmol, 0.053 g). The reaction mixture was stirred at reflux for 1 .5 hr, and then cooled to rt and concentrated in vacuo to obtain methyl 4-(4,5-dimethylpyrazol-1-yl) quinoline-2-carboxylate as a mixture with methyl 4-(5-ethylpyrazol-1-yl) quinoline- 2-carboxylate. This was used in the next step without further purification. LCMS: (Method A); Rt = 0.94 min, m / z = 282 [M+H]+’ both isomers

[0388] Step 5: Preparation of 4-(4,5-dimethylpyrazol-1-yl)-A / -pentyl-quinoline-2-carboxamide (Compound P-1 , Table El

[0389] A sample of methyl 4-(4,5-dimethylpyrazol-1-yl) quinoline-2-carboxylate (180 mg, 0.64 mmol) was dissolved in toluene (0.64 mL). To this solution was added pentan-1 -amine (0.089 mL, 0.77 mmol) and 1 ,5,7- triazabicyclo[4.4.0]dec-5-en (TBD, 0.027g, 0.19 mmol) and the reaction mixture was monitored by LCMS. Upon reaction completion, the mixture was diluted with EtOAc and water. The aqueous layer was extracted once with EtOAc and the combined organic layers were dried, filtered and concentrated in vacuo. The crude material was purified by CombiFlash with EtOAc in cyclohexane (0-40% EtOAc) to obtain the title compound containing 30% of 4-(5-ethylpyrazol-1-yl)-N-pentyl-quinoline-2-carboxamide. LCMS (Method A): Rt = 1.14 min, m / z = 337 [M+H]+;1H NMR (400 MHz, CDCI3) 5 ppm 0.96 (t, J=7.1 Hz, 3 H) 1 .39 - 1 .50 (m, 4 H) 1 .74 (br t, J=7.1 Hz, 2 H) 2.16 (s, 3 H) 2.18 (s, 3 H) 3.53 - 3.63 (m, 2 H) 7.61 - 7.71 (m, 2 H) 7.77 - 7.88 (m, 2 H) 8.18 - 8.24 (m, 2 H) 8.28 (s, 1 H)

[0390] Example P2: Preparation of A / -pentyl-4-(3,4,5-trimethylpyrazol-1-yl) quinoline-2-carboxamide (Compound P-

[0391] 15, Table P)

[0392] (Compound P-15, Table P)

[0393] Step 1 : Preparation of methyl 4-(3,4,5-trimethylpyrazol-1-yl) quinoline-2-carboxylate

[0394] In a round bottom flask, equipped with a condenser, was added methyl 4-hydrazinoquinoline-2-carboxylate hydrochloride salt (40 mg, 0.158mmol) and 3-methyl-2,4-pentanedione (0.021 mL, 0.17 mmol) in acetic acid (0.45 mL). The reaction mixture was stirred at reflux for 45 min and then evaporated to afford the title compound as a yellow solid. LCMS (Method A): Rt = 0.95 min, m / z = 296 [M+H]+

[0395] Step 2: Preparation of 4-(3,4,5-trimethylpyrazol-1-yl) quinoline-2-carboxylic acid A solution of methyl 4-(3,4,5-trimethylpyrazol-1-yl) quinoline-2-carboxylate 01 (47 mg, 0.16 mmol) in THF (0.48 mL) and water (0.48 mL) was treated with lithium hydroxide monohydrate (0.007 g, 0.16 mmol) and the mixture stirred at rt. After 1.5 hr, the reaction mixture was concentrated in vacuo to obtain 4-(3,4,5-trimethylpyrazol-1- yl) quinoline-2-carboxylic acid as a lithium salt. LCMS (Method A): Rt = 0.39 min, m / z = 269 [M+H]+;1H NMR (400 MHz, d6-DMSO) 5 = 8.10 (br d, J = 8.4 Hz, 1 H), 7.95 (s, 1 H), 7.87 (br t, J = 7.1 Hz, 1 H), 7.73 - 7.61 (m, 2H), 2.22 (s, 3H), 2.08 (s, 3H), 2.03 (s, 3H)

[0396] Step 3: Preparation of A / -pentyl-4-(3,4,5-trimethylpyrazol-1-yl) quinoline-2-carboxamide (Compound P-15,

[0397] Table P)

[0398] A sample of 4-(3,4,5-trimethylpyrazol-1-yl) quinoline-2-carboxylic acid (40 mg, 0.14 mmol) was dissolved in EtOAc (0.70 mL) and pentan-1 -amine (0.017 mL, 0.15 mmol) and N,N-diisopropylethylamine (0.074 mL, 0.42 mmol) are added. To this mixture was added T3P (50% in EtOAc) (0.15 mL, 0.25 mmol) and the reaction mixture was stirred at rt. Further aliquot’s of T3P (50% in EtOAc) (50 mass%) and N, N-diisopropylethylamine (99 mass%) were added until the reaction reached full conversion (7 equiv. of T3P in total, 12 equiv. Hunig Base). The reaction mixture was diluted with EtOAc and water, the organic phase separated, and the aqueous phase extracted with EtOAc. The combined organic layers were washed once with brine, dried over MgSO4, filtered, and concentrated in vacuo. The crude material was purified by CombiFlash over silica gel (12 g, 0-60% EtOAc in cyclohexane to obtain the title compound as an orange oil. LCMS (Method A); Rt = 1.18 min, m / z = 351 [M+H]+;1H NMR (400 MHz, CDCI3) 5 = 8.36 - 8.28 (m, 1 H), 8.22 - 8.18 (m, 2H), 7.90 (dd, J = 0.7, 8.4 Hz, 1 H), 7.81 (ddd, J = 1 .5, 6.9, 8.4 Hz, 1 H), 7.63 (ddd, J = 1 .1 , 7.0, 8.3 Hz, 1 H), 3.61 - 3.49 (m, 2H), 2.32 (s, 3H), 2.16 (s, 3H), 2.07 (s, 3H), 1.74 (br t, J = 7.3 Hz, 2H), 1.48 - 1.39 (m, 5H), 0.99 - 0.92 (m, 3H) l-1-yl)-A / -pentyl-quinoline-2-carboxamide P-3

[0399] (Compound P-3, Table P) ic acid

[0400] To a solution of methyl 4-bromoquinoline-2-carboxylate (1.5g, 5.6 mmol) in THF / H2O 3:1 (45 mL). was added lithium hydroxide monohydrate (270 mg, 6.2 mmol1) and the reaction mixture stirred at rt for 45 min. The white suspension was diluted with EtOAc and HCI (1 M), the EtOAc phase separated, and the aqueous phase extracted with EtOAc (X3). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo to obtain the title compound.1H NMR (400 MHz, d6-DMSO) 5 ppm 7.89 - 7.95 (m, 1 H) 7.99 (ddd, J=8.36, 6.90, 1.45 Hz, 1 H) 8.23 (ddd, J=8.36, 3.81 , 0.91 Hz, 2 H) 8.35 - 8.43 (m, 1 H) 13.6 - 13.8 (br s, 1 H) Step 2: Preparation of 4-bromo-A / -pentyl-quinoline-2-carboxamide

[0401] To a solution of 4-bromoquinoline-2-carboxylic acid (1 .34 g, 5.31 mmol) and pentan-1-amine (0.952., 8.2400 mmol) in EtOAc (10 mL) was added T3P 50 % in EtOAc (11 ,1 mL, 18.60 mmol) and DIPEA (3.64 mL 21.264 mmol) at rt. The reaction mixture was stirred at rt, monitoring by LCMS. Upon reaction completion, the orange solution was quenched with sat. aqueous NaHCOs. This was diluted with EtOAc, the organic phase separated, and the aqueous layer extracted with EtOAc (x3). The combined organic phases were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude obtained was purified by chromatography over silica gel to afford the title compound. LCMS (Method A): Rt= 1.24 min, m / z = 321 / 323 [M+H]+;1H NMR (400 MHz, CDCI3) 5 ppm 0.91 - 1.00 (m, 3 H) 1.37 - 1.49 (m, 4 H) 1.68 - 1.77 (m, 2 H) 3.51 - 3.59 (m, 2 H) 7.71 - 7.76 (m, 1 H) 7.81 - 7.86 (m, 1 H) 8.12 - 8.16 (m, 1 H) 8.17 - 8.24 (m, 1 H) 8.25 - 8.29 (m, 1 H) 8.60 - 8.66 (m, 1 H)

[0402] Step 3: Preparation of 4-(4,5-dimethylimidazol-1-yl)-A / -pentyl-quinoline-2-carboxamide (Compound P-3, Table

[0403] El

[0404] To a solution of 4-bromo-A / -pentyl-quinoline-2-carboxamide (60 mg, 0.18 mmol) in DMSO (0.37 mL) under argon atmosphere were added Copper(l) iodide (7 mg, 0.037 mmol) and 4,5-dimethyl-1 H-imidazole (17 mg, 0.186 mmol), potassium phosphate tribasic (2 equiv., 0.37358472 mmol, 0.0809169 g) and picolinic acid (0.2 equiv., 0.037 mmol, 4.6 mg). The resulting mixture was stirred at 90°C for 48 hr. The reaction mixture was diluted with EtOAc and water, the organic phase was separated, and the aqueous phase extracted with EtOAc (x2). The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo to afford the crude material as a yellow oil (50mg). The crude material was purified on CombiFlash over silica gel (12g 0-100% EtOAc in cyclohexane) and then by reverse phase HPLC to obtain the title compound. LCMS (Method A): Rt = 0.84 min, m / z = 337 [M+H]+;1H NMR (400 MHz, CDCI3) 5 = 8.34 - 8.13 (m, 3H), 7.87 (dt, J = 1.3, 7.7 Hz, 1 H), 7.67 (dt, J = 1.1 , 7.6 Hz, 1 H), 7.61 (s, 1 H), 7.56 (d, J = 8.0 Hz, 1 H), 3.62 - 3.51 (m, 2H), 2.33 (s, 3H), 1 .99 (s, 3H), 1 .74 (quin, J = 7.3 Hz, 2H), 1 .55 - 1 .30 (m, 4H), 1 .00 - 0.83 (m, 3H)

[0405] Example P4: Preparation of 4-(3,4-dimethylpyrazol-1-yl)-N-pentyl-quinoline-2-carboxamide (Compound P-21 ,

[0406] Table P)

[0407] (Compound P-21 , Table P)

[0408] In a Supelco® vial containing 4-bromo-A / -pentyl-quinoline-2-carboxamide (100 mg, 0.31 mmol) dissolved in acetonitrile (0.62 mL) was added copper(l) oxide (22 mg, 0.016 mmol), 4,5-dimethyl-1 H-pyrazole (30 mg, 0.31 mmol), caesium carbonate (200 mg, 0.62 mmol), and salicylaldoxime (8.7 mg, 0.062 mmol), under argon. The resulting mixture was stirred at reflux for 12 hrs, whereupon LCMS showed reaction completion. The reaction mixture was cooled to rt, diluted with EtOAc and water, the aqueous layer separated and extracted with EtOAc (x2). The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by chromatography over silica gel to afford the title compound. LCMS (Method A): Rt = 1.20 min, m / z = 337 [M+H]+;1H NMR (400 MHz, CDCI3) 5 = 8.34 - 8.13 (m, 3H), 7.87 (dt, J = 1.3, 7.7 Hz, 1 H), 7.67 (dt, J = 1.1 , 7.6 Hz, 1 H), 7.61 (s, 1 H), 7.56 (d, J = 8.0 Hz, 1 H), 3.62 - 3.51 (m, 2H), 2.33 (s, 3H), 1.99 (s, 3H), 1 .74 (quin, J = 7.3 Hz, 2H), 1 .55 - 1 .30 (m, 4H), 1 .00 - 0.83 (m, 3H)

[0409] Example P5: Preparation of 4-(4,5-dimethyltriazol-1-yl)-N-pentyl-quinoline-2-carboxamide (Compound P-2,

[0410] (Compound P-3, Table P)

[0411] Step 1 : Preparation of 4-azido-A / -pentyl-quinoline-2-carboxamide

[0412] To a solution of 4-bromo-A / -pentyl-quinoline-2-carboxamide (0.629 g, 1.95 mmol) in DMF (4 mL) was added sodium azide (0.402 g, 5.87 mmol). The resulting reaction mixture was stirred at 90°C for 4 hrs, cooled to rt and poured into water. The mixture was extracted with EtOAc (x2), and the combined organic phases were washed with water, brine, dried over MgSO4, filtered, and concentrated in vacuo to obtain the title compound which was used as such in the next step. LCMS (Method A): Rt=1 .17min, m / z 284 [M+H]+;1H NMR (400 MHz, CDCI3) 5: 8.27 (br t, 1 H), 8.13 (s, 1 H), 8.07-8.12 (m, 2H), 7.80 (ddd, 1 H), 7.62 (ddd, 1 H), 3.52-3.59 (q, 2H), 1 .73 (m, 2H), 1 .37-1 .49 (m, 4H), 0.92-1 .00 (t, 3H)

[0413] Step 2: Preparation of 4-(4,5-dimethyltriazol-1-yl)-N-pentyl-quinoline-2-carboxamid (Compound P-3, Table P) A sample of 4-azido-N-pentyl-quinoline-2-carboxamide (0.100 g, 0.353 mmol) was placed in a miniclave reactor with but-2-yne (0.53 mL) and toluene (0.53 mL) and stirred at 120°C for 40 hrs. The reaction mixture was cooled, diluted with water, and extracted with EtOAc. The organic phase was washed with water, brine, dried over MgSO4, filtered, and concentrated in vacuo. The crude product was purified by chromatography over silica gel and then the fractions containing the desired product, contaminated with 4-amino-A / -pentyl-quinoline-2- carboxamide, were concentrated in vacuo and purified with reversed phase HPLC eluting with Solvent A: Water + 0,1 % formic acid; Solvent B: ACN + 0,1 % formic acid, 10-90%. The fractions containing product were concentrated in vacuo, taken up in EtOAc, washed with sat. NaHCOs, dried over Na2SO4 and concentrated in vacuo to obtain the title compound. LCMS (Method A): Rt =1.06min, m / z 338 [M+H]+;1H NMR (400 MHz, CDCI3) 5: 8.23-8.31 (m, 3H), 7.85-7.92 (m, 1 H), 7.65-7.72 (m, 1 H), 7.57-7.64 (m, 1 H), 3.54-3.63 (q, 2H), 2.43-

[0414] 2.49 (s, 3H), 2.16-2.22 (s, 3H), 1.70-1.80 (m, 2H), 1.36-1.50 (m, 4H), 0.92-1 .00 (m, 3H)

[0415] Example P6: Preparation of 4-(5-chloro-1-methyl-imidazol-4-yl)-N-pentyl-quinoline-2-carboxamide

[0416] P-9, Table

[0417] (Compound P-9, Table P)

[0418] Step 1 : Preparation of N-pentyl-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl) quinoline-2-carboxamide

[0419] A suspension of 4-bromo-A / -pentyl-quinoline-2-carboxamide (0.406 g, 1.264 mmol), 4,4,5,5-tetramethyl-2- (4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 ,3,2-dioxaborolane (0.417 g, 1.643 mmol), and potassium acetate (0.372 g, 3.792 mmol) in 2-methyltetrahydrofuran (2.5 mL), was flushed with argon and 1 ,T- bis(diphenylphosphino)ferrocene-palladium(ii)dichloride dichloromethane complex (0.05266 g, 0.06320 mmol) was added. The resulting reaction mixture was stirred at 75°C, monitoring by LCMS. Upon completion, the reaction mixture was cooled to rt and diluted water and EtOAc. The EtOAc phase was separated, and the aqueous phase extracted with EtOAc. The combined organic phases were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The crude product was purified by chromatography over silica gel to afford the title compound. LCMS (Method A): Rt= 1.29 min, m / z = 369 [M+H]+;1H NMR (400 MHz, Solvent) 5 ppm 0.92 - 0.98 (m, 3 H) 1.28 (s, 12 H) 1.46 - 1.47 (m, 4 H) 1.69 - 1.79 (m, 2 H) 3.52 - 3.60 (m, 2 H) 7.66 - 7.73 (m, 1 H) 7.77 - 7.85 (m, 1 H) 8.23 - 8.30 (m, 1 H) 8.50 - 8.59 (m, 1 H) 8.69 - 8.75 (m, 1 H) 8.80 - 8.84 (m, 1 H)

[0420] Step 2: Preparation of 4-(5-chloro-1-methyl-imidazol-4-yl)-N-pentyl-quinoline-2-carboxamide (Compound P-9, Table P)

[0421] In a Supelco® vial under argon atmosphere, N-pentyl-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)quinoline- 2-carboxamide (0.050 g, 0.136 mmol), 4-bromo-5-chloro-1-methyl-imidazole (0.032 g, 0.149 mmol), XPhos- Pd-G3 (0.011 g, 0.0136 mmol), caesium carbonate (0.0889 g, 0.272 mmol), in 2-methyltetrahydrofuran / water (4 / 1 ) (5 mL) were stirred 10 min at rt and 12 hrs at 80°C. The reaction mixture was cooled to rt and diluted water and EtOAc. The EtOAc phase was separated, and the aqueous phase extracted with EtOAc. The combined organic phases were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude was purified by chromatography over silica gel to afford the title compound. LCMS (Method A): Rt: 1 .08 min, m / z = 357 [M+H]+;1H NMR (400 MHz, CDCI3) 5 ppm 8.54 (d, J=8.0 Hz, 1 H) 8.50 - 8.52 (m, 1 H) 8.38 (br t, J=5.3 Hz, 1 H) 8.16 (d, J=8.0 Hz, 1 H) 7.73 - 7.80 (m, 2 H) 7.61 (ddd, J=8.3, 7.0, 1.1 Hz, 1 H) 3.75 (s, 3 H) 3.51 - 3.61 (m, 2 H) 1 .73 (quin, J=7.3 Hz, 2 H) 1 .35 - 1 .50 (m, 4 H) 0.87 - 0.99 (m, 3 H)

[0422] In a Supelco® vial under argon atmosphere, N-pentyl-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)quinoline- 2-carboxamide (0.0840 g, 0.228 mmol), 2-bromo-1 ,5-dimethyl-imidazole (0.0439 g, 0.251 mmol), potassium hydroxide (0.0301 g, 0.456 mmol), PdCI(crotyl)amphos (0.0108 g, 0.0228 mmol), 2- methyltetrahydrofuran / water (4 / 1 ) (5 mL) were mixed together and the resulting mixture was stirred 10 min at rt and then 3 hrs at 80°C. The reaction mixture was cooled to rt and diluted water and EtOAc. The EtOAc phase was separated, and the aqueous phase extracted with EtOAc. The combined organic phases were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude was purified by chromatography over silica gel to afford 4-(1 ,5-dimethylimidazol-2-yl)-N-pentyl-quinoline-2-carboxamide. LCMS (Method A): Rt = 0.83 min, m / z = 337 [M+H]+;1H NMR (400 MHz, CDCI3) 5 ppm 8.31 (s, 2 H) 8.26 (d, J=8.4 Hz, 1 H) 8.17 (d, J=8.0 Hz, 1 H) 7.79 (td, J=7.6, 1.1 Hz, 1 H) 7.60 - 7.67 (m, 1 H) 7.10 (s, 1 H) 3.51 - 3.61 (m, 5 H) 2.36 (s, 3 H) 1 .73 (quin, J=7.3 Hz, 2 H) 1 .36 - 1 .51 (m, 4 H) 0.91 - 1 .00 (m, 3 H)

[0423] Example 8: Preparation of 4-(1 ,5-dimethyltriazol-4-yl)-N-pentyl-quinoline-2-carboxamide (Compound P-14,

[0424] Table

[0425] (Compound P-14, Table P)

[0426] In a Supelco® vial under an argon atmosphere, a suspension of N-pentyl-4-(4,4,5,5-tetramethyl-1 ,3,2- dioxaborolan-2-yl)quinoline-2-carboxamide (50 mg, 0.136 mmol), 4-bromo-1 ,5-dimethyl-triazole (26 mg, 0.149 mmol), potassium carbonate (37 mg, 0.272 mmol), PdCI(crotyl)amphos (6 mg, 0.013 mmol), in 2-methyl tetrahydrofuran / water (1 / 1 ) (5 mL) were stirred 10 min at rt and then for 3 hr at 80°C. The reaction mixture was cooled to rt and diluted water and EtOAc. The EtOAc phase was separated, and the aqueous phase extracted with EtOAc. The combined organic phases were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by chromatography over silica gel to afford the title compound. LCMS (Method A): Rt= 1 .01 min, m / z = 338 [M+H]+;1H NMR (400 MHz, CDCI3) 6 ppm 8.39 - 8.48 (m, 1 H) 8.34 (br t, J=5.4 Hz, 1 H) 8.26 (s, 1 H) 8.18 (d, J=8.0 Hz, 1 H) 7.80 (ddd, J=8.4, 6.9, 1.5 Hz, 1 H) 7.64 (ddd, J=8.4, 6.9, 1.1 Hz, 1 H) 4.13 (s, 3 H) 3.50 - 3.61 (m, 2 H) 2.46 (s, 3 H) 1.69 - 1.82 (m, 2 H) 1.36 - 1.50 (m, 4 H) 0.92 - 1.01 (m, 3 H) i-2-carboxamide

[0427] Compound P-19, Table P

[0428] Step 1 : Preparation of methyl 4-(5-chloro-1-methyl-triazol-4-yl) quinoline-2-carboxylate

[0429] In a Supelco® vial, a suspension of methyl 4-bromoquinoline-2-carboxylate (200 mg, 0.752 mmol), 5-chloro-1- methyl-triazole (133 mg, 1 .13 mmol), pivalic acid (23 mg, 0.225 mmol), potassium carbonate (273 mg, 1.88 mmol) and N,N-dimethylacetamide (4.13 mL), in toluene (4 mL) was flushed with argon, and then treated with Palladium(ll) acetate (0.0172 g, 0.0752 mmol, 0.100 equiv.) was added and the reaction mixture was stirred at 120°C, monitoring by HPLC. Upon reaction completion, the reaction mixture was cooled, diluted with water, and extracted with EtOAc (x3). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was used in the next step without further purification. LCMS (Method A): Rt=0.82min, m / z = 303 [M+H]+

[0430] Step 2: Preparation of 4-(5-chloro-1-methyl-triazol-4-yl)-A / -(3-cyclopropylpropyl)quinoline-2-carboxamide (Compound P-19, Table P)

[0431] In a Supelco® vial, a solution of methyl 4-(5-chloro-1 -methyl-triazol-4-yl)quinoline-2-carboxylate (60mg, 0.1 mmol) in toluene (0.15 mL) was treated with 3-cyclopropylpropan-1 -amine (9.8 mg, 0.1 mmol) and 1 ,5,7- triazabicyclo[4.4.0]dec-5-en (4,2 mg, 0.030 mmol). The reaction mixture was stirred at 70°C for 1 hr, upon which LCMS analysis showed complete conversion. The reaction mixture was cooled, diluted with water, and extracted with EtOAc (x3). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by CombiFlash chromatography eluting with cyclohexane / EtOAc to give the title compound as a yellow oil. LCMS (Method A) Rt=1 .12min, m / z = 370 [M+H]+;1H NMR (400 MHz, CDCI3) 5: 8.52 (s, 1 H), 8.47-8.49 (d, 1 H), 8.27-8.39 (br t, 1 H), 8.20 (d, 1 H), 7.83 (ddd, 1 H), 7.68 (ddd, 1 H), 4.20 (s, 3H), 3.62 (q, 2H), 1 .86 (quint, 2H), 1 .34-1 .44 (m, 2H), 0.73-0.82 (m, 1 H), 0.43-0.53 (m, 2H), 0.03-0.15 (m, 2H)

[0432] Examples of synthesized compounds are shown in Table P.

[0433] Table P: Synthesized compounds and spectral and physical chemical data

[0434]

[0435]

[0436] BIOLOGICAL EXAMPLES

[0437] Example B1 : Alternaria solani / tomato / (early blight)

[0438] Tomato leaf disks cv. Baby are placed on agar in multiwell plates (24-well format) and sprayed with the formulated test compound diluted in water. The leaf disks are inoculated with a spore suspension of the fungus

[0439] 2 days after application. The inoculated leaf disks are incubated at 23°C / 21 °C (day / night) and 80% rh under a light regime of 12 / 12 h (light / dark) in a climate cabinet and the activity of a compound is assessed as percent disease control compared to untreated when an appropriate level of disease damage appears on untreated check disk leaf disks (5 to 7 days after application). The following compounds gave at least 80% control of Alternaria solani at 200 ppm when compared to untreated control under the same conditions, which showed extensive disease development: P-2, P-3, P-4, P-14

[0440] Example B2.~ Botryotinia fuckeliana (Botrytis cinerea) / (Gray mould)

[0441] Conidia of the fungus from cryogenic storage are directly mixed into nutrient broth (Vogels broth). After placing a (DMSO) solution of test compound into a microtiter plate (96-well format), the nutrient broth containing the fungal spores is added. The test plates are incubated at 24°C and the inhibition of growth is determined photometrically 3 to 4 days after application. The following compounds gave at least 80% control of Botryotinia fuckeliana at 20 ppm when compared to untreated control under the same conditions, which showed extensive disease development: P-2, P-3

[0442] Example B3: Glomerella lagenarium (Colletotrichum laqenarium) / (Anthracnose) Conidia of the fungus from cryogenic storage are directly mixed into nutrient broth (PDB potato dextrose broth). After placing a (DMSO) solution of test compound into a microtiter plate (96-well format), the nutrient broth containing the fungal spores is added. The test plates are incubated at 24°C and the inhibition of growth is measured photometrically 3 to 4 days after application. The following compounds gave at least 80% control of Glomerella lagenarium at 20 ppm when compared to untreated control under the same conditions, which showed extensive disease development: P-1 , P-9, P-14 f. sp. tritici) / wheat / mildew on

[0443] Wheat leaf segments cv. Kanzler are placed on agar in a multiwell plate (24-well format) and sprayed with the formulated test compound diluted in water. The leaf disks are inoculated by shaking powdery mildew infected plants above the test plates 1 day after application. The inoculated leaf disks are incubated at 20°C and 60% rh under a light regime of 24 h darkness followed by 12 h light / 12 h darkness in a climate chamber and the activity of a compound is assessed as percent disease control compared to untreated when an appropriate level of disease damage appears on untreated check leaf segments (6 to 8 days after application). The following compounds gave at least 80% control of Blumeria graminis f. sp. tritici at 200 ppm when compared to untreated control under the same conditions, which showed extensive disease development: P-2, P-4

[0444] Example B5: Fusarium culmorum I (Head blight)

[0445] Conidia of the fungus from cryogenic storage are directly mixed into nutrient broth (PDB potato dextrose broth). After placing a (DMSO) solution of test compound into a microtiter plate (96-well format), the nutrient broth containing the fungal spores is added. The test plates are incubated at 24°C and the inhibition of growth is determined photometrically 3 to 4 days after application. The following compounds gave at least 80% control of Fusarium culmorum at 20 ppm when compared to untreated control under the same conditions, which showed extensive disease development: P-2, P-9, P-14, P-18

[0446] Example B6: Gibberella zeae (Fusarium graminearum) / wheat / (Head blight)

[0447] Wheat spikelets cv. Monsun are placed on agar in multiwell plates (24-well format) and sprayed with the formulated test compound diluted in water. One day after application, the spikelets are inoculated with a spore suspension of the fungus. The inoculated test leaf disks are incubated at 20°C and 60% rh under a light regime of 72 h semi darkness followed by 12 h light / 12 h darkness in a climate chamber, the activity of a compound is assessed as percent disease control compared to untreated when an appropriate level of disease damage appears on untreated check spikelets (6 to 8 days after application). The following compounds gave at least 80% control of Gibberella zeae at 200 ppm when compared to untreated control under the same conditions, which showed extensive disease development: P-2

[0448] Example B7: Phaeosphaeria nodorum (Septoria nodorum) / wheat / (Glume blotch)

[0449] Wheat leaf segments cv. Kanzler are placed on agar in a multiwell plate (24-well format) and sprayed with the formulated test compound diluted in water. The leaf disks are inoculated with a spore suspension of the fungus 2 days after application. The inoculated test leaf disks are incubated at 20 °C and 75% rh under a light regime of 12 h light / 12 h darkness in a climate cabinet and the activity of a compound is assessed as percent disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf disks (5 to 7 days after application). The following compounds gave at least 80% control of Phaeosphaeria nodorum at 200 ppm when compared to untreated control under the same conditions, which showed extensive disease development: P-1 , P-3, P-4, P-13, P-14, P-18, P-19

[0450] Conidia of the fungus from cryogenic storage are directly mixed into nutrient broth (PDB potato dextrose broth). After placing a (DMSO) solution of test compound into a microtiter plate (96-well format), the nutrient broth containing the fungal spores is added. The test plates are incubated at 24°C and the inhibition of growth is determined photometrically 4 to 5 days after application. The following compounds gave at least 80% control of Monographella nivalis at 20 ppm when compared to untreated control under the same conditions, which showed extensive disease development: P-2, P-18

[0451] Example B9: Maqnaporthe arisea (Pyricularia orvzae) / (Rice Blast)

[0452] Conidia of the fungus from cryogenic storage are directly mixed into nutrient broth (PDB potato dextrose broth). After placing a (DMSO) solution of test compound into a microtiter plate (96-well format), the nutrient broth containing the fungal spores is added. The test plates are incubated at 24°C and the inhibition of growth is determined photometrically 3 to 4 days after application. The following compounds gave at least 80% control of Magnaporthe grisea at 20 ppm when compared to untreated control under the same conditions, which showed extensive disease development: P-2, P-9, P-14, P-18

[0453] Example B10: Pyrenophora teres I barlev / (Net blotch)

[0454] Barley leaf segments cv. Hasso are placed on agar in a multiwell plate (24-well format) and sprayed with the formulated test compound diluted in water. The leaf segments are inoculated with a spore suspension of the fungus 2 days after application. The inoculated leaf segments are incubated at 20°C and 65% rh under a light regime of 12 h light / 12 h darkness in a climate cabinet and the activity of a compound is assessed as disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf segments (5 to 7 days after application). The following compounds gave at least 80% control of Pyrenophora teres at 200 ppm when compared to untreated control under the same conditions, which showed extensive disease development: P-2, P-3, P-4, P-9, P-12, P-13, P-14, P-18, P-19

[0455] Example B11 : Thanatephorus cucumeris (Rhizoctonia solani) / (foot rot, damping-off)

[0456] Mycelia fragments of a newly grown liquid culture of the fungus are directly mixed into nutrient broth (PDB potato dextrose broth). After placing a (DMSO) solution of the test compounds into a microtiter plate (96-well format), the nutrient broth containing the fungal material is added. The test plates are incubated at 24°C and the inhibition of growth is determined photometrically 3 to 4 days after application. The following compounds gave at least 80% control of Thanatephorus cucumeris at 20 ppm when compared to untreated control under the same conditions, which showed extensive disease development: P-2, P-14

[0457] Conidia of the fungus from cryogenic storage are directly mixed into nutrient broth (PDB potato dextrose broth). After placing a (DMSO) solution of test compound into a microtiter plate (96-well format), the nutrient broth containing the fungal spores is added. The test plates are incubated at 24°C and the inhibition of growth is determined photometrically 4 to 5 days after application. The following compounds gave at least 80% control of Mycosphaerella graminicola at 20 ppm when compared to untreated control under the same conditions, which showed extensive disease development: P-1 , P-2, P-3, P-6, P-8, P-9, P-10, P-11 , P-12, P-13, P-14, P- 15, P-18, P-19

[0458] Example B13: Corynespora cassiicola (target leaf spot of tomato):

[0459] Conidia of the fungus from cryogenic storage were directly mixed into nutrient broth (PDB potato dextrose broth). A DMSO solution of the test compounds was placed into a microtiter plate (96-well format) and the nutrient broth containing the fungal spores was added to it. The test plates were incubated at 24°C and the inhibition of growth was determined photometrically after 3 to 4 days at 620nm. The following compounds gave at least 80% control of Corynespora cassiicola at 20 ppm when compared to untreated control under the same conditions, which showed extensive disease development: P-2

Claims

1. CLAIMS1. A compound of formula (I):whereinR1is selected from hydrogen, halogen, cyano, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkyl, C3-C6- cycloalkyl, Ci-C4-alkylsulfanyl, Ci-C4-alkylsulfinyl, or Ci-C4-alkylsulfonyl;R2is selected from hydrogen, halogen, cyano, or Ci-C4-alkyl;B1is selected from CR4, or N;B2is selected from CR5, or N;R3, R4and R5are independently selected from hydrogen, halogen, cyano, hydroxy, amino, carboxy, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-haloalkoxy, Ci-C4-alkoxy, Cs-Cs-alkenyloxy, Cs-Ce-alkynyloxy, C1- C4-alkylsulfanyl, Ci-C4-alkylsulfinyl, Ci-C4-alkylsulfonyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4- alkoxy, Ci-C4-alkoxycarbonyl, Ci-C4-alkylcarbonyl, carbamoyl, Ci-C4-alkylaminocarbonyl, di(Ci-Ce- alkyl)aminocarbonyl, cyano-Ci-C4-alkyl, N-Ci-C4-alkoxy-C-Ci-C4-alkyl-carbonimidoyl, N-hydroxy-C- Ci-C4-alkyl-carbonimidoyl, Ci-C4-alkylamino, Ci-C4-dialkylamino, Ci-C4-alkylaminocarbonyl, C1-C4- dialkylaminocarbonyl, trifluoromethylsulfonyloxy, phenyl, a 5- to 6-membered saturated, partially saturated or aromatic heteroaryl, or Cs-Ce-cycloalkyl; wherein any of said heteroaryl contains 1 , 2 or 3 heteroatoms independently selected from O, S, or N, with the proviso that only one is selected from O or S; wherein any of said phenyl and 5- to 6-membered saturated, partially saturated or aromatic heteroaryl are unsubstituted or substituted with 1 , 2, or 3 substituents independently selected from halogen, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, or Ci-C4-alkoxy; and wherein any of said Cs-Ce-cycloalkyl is unsubstituted or substituted with 1 , 2 or 3 substituents independently selected from halogen, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, or Ci-C4-alkoxy;Q is a 5-membered aromatic heteroaryl, wherein said 5-membered aromatic heteroaryl is selected from pyrrol-1 -yl, pyrrol-2-yl, pyrrol-3-yl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-5-yl, imidazole-1-yl, imidazole2-yl, imidazole-4-yl, triazol-1 -yl, triazol-2-yl, triazol-4-yl, 1 ,2,4-triazol-1 -yl, 1 ,2,4-triazol-3-yl, or tetrazol-5-yl; wherein any of said pyrrole-moieties, pyrazole-moieties, imidazole-moieties and tetrazole-moieties is substituted at the carbon-atoms by 1 or 2 substituents independently selected from R6; and is substituted at one of the nitrogen atoms by one substituent selected from R7; wherein R6is selected from hydrogen, halogen, cyano, hydroxy, amino, Ci-C4-alkyl, C2-C4-alkenyl, C2- C4-alkynyl, Ci-C4-haloalkyl, Cs-Ce-cycloalkyl, Ci-C4-alkoxy, Ci-C4-alkylamino, di(Ci-C4-alkyl)amino, C1- C4-haloalkoxy, Ci-C4-halosulfanyl, Cs-Cs-alkenyloxy, Cs-Ce-alkynyloxy, Cs-Ce-cycloalkyloxy, C1-C4- alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy, Ci-C4-alkylsulfanyl, Ci-C4-alkylsulfinyl, or C1-C4- alkylsulfonyl; andwherein R7is selected from hydrogen, or Ci-C4-alkyl; andZ1is selected from Ci-Cs-alkyl, wherein said Ci-Cs-alkyl is unsubstituted or substituted with 1 , 2 or 3 substituents independently selected halogen, hydroxy, cyano, carboxy, Ci-C4-alkyl, C2-Cs-alkenyl, C2- Ce-alkynyl, Ci-C4-haloalkyl, Ci-C4-haloalkoxy, Ci-C4-alkoxy, C2-Cs-alkenyloxy, C2-Ce-alkynyloxy, C1- C4-alkylsulfanyl, Ci-C4-alkylsulfinyl, Ci-C4-alkylsulfonyl, Ci-C4-haloalkylsulfanyl, C1-C4- halkoalkylsulfinyl, Ci-C4-haloalkylsulfonyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy, C1-C4- alkylcarbonyl, Ci-C4-alkoxycarbonyl, N-Ci-C4-alkoxy-C-Ci-C4-alkyl-carbonimidoyl, N-hydroxy-C-Ci- C4-alkyl-carbonimidoyl, trifluoromethylsulfonyloxy, phenyl, a 5- to 6-membered saturated, partially saturated or aromatic heteroaryl, or Cs-Ce-cycloalkyl; wherein any of said heteroaryl contains 1 , 2 or 3 heteroatoms independently selected from O, S, or N, with the proviso that only one is selected from O or S; wherein any of said phenyl, 5- to 6-membered saturated, partially saturated or aromatic heteroaryl, are unsubstituted or substituted with 1 , 2 or 3 substituents independently selected from halogen, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, or Ci-C4-alkoxy; and wherein said Cs-Ce-cycloalkyl is unsubstituted or substituted with 1 , 2 or 3 substituents independently selected from halogen, cyano, Ci-C4-alkyl, C1-C4- haloalkyl, or Ci-C4-alkoxy; or an agrochemically acceptable salt, or N-oxide thereof.

2. The compound according to claim 1 , wherein R1, R2and R3are hydrogen.

3. The compound according to claim 1 or claim 2, wherein B1is CR4; and B2is CR5; wherein R4and R5are independently selected from hydrogen, halogen, cyano, Ci-Cs-alkyl, Ci-Cs-alkoxy, C1-C2- alkoxycarbonyl, or C3-C4-cycloalkyl.

4. The compound according to any one of claims 1 to 3, wherein Q is a 5-membered aromatic heteroaryl, wherein said 5-membered aromatic heteroaryl is selected from pyrrol-1-yl, pyrrol-2-yl, pyrrol-3-yl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-5-yl, imidazole-1-yl, Imidazole2-yl, imidazole-4-yl, triazol-1 -yl, triazol- 2-yl, triazol-4-yl, 1 ,2,4-triazol-1 -yl, 1 ,2,4-triazol-3-yl, or tetrazo l-5-y I; wherein any of said pyrrole- moieties, pyrazole-moieties, imidazole-moieties and tetrazole-moieties is substituted at the carbon- atoms by 1 or 2 substituents independently selected from R6; and is substituted at one of the nitrogen atoms by one substituent selected from R7; wherein R6is hydrogen, halogen, Ci-Cs-alkyl, Ci-Cs-alkoxy, or Ci-C2-alkylsulfanyl; and R7is hydrogen or methyl.

5. The compound according to any one of claims 1 to 4, wherein Q is a 5-membered aromatic heteroaryl, wherein said 5-membered aromatic heteroaryl is selected fromwherein the staggered line denotes the attachment point of the Q substituent to the rest of the molecule; R6a, R6b, R6cand R6dare independently selected from hydrogen, halogen, Ci-Cs-alkyl, Ci-Cs-alkoxy, orCi-C2-alkylsulfanyl; and R7is hydrogen or Ci-Cs-alkyl.

6. The compound according to any one of claims 1 to 5, wherein Q is a 5-membered aromatic heteroaryl selected fromwherein the staggered line denotes the attachment point of the Q substituent to the rest of the molecule; R6a, R6b, R6cand R6dare independently selected from hydrogen, hydrogen, chloro, methyl, methoxy, or methylsulfanyl; and R7is hydrogen or Ci-Cs-alkyl.

7. The compound according to any one of claims 1 to 6, wherein Q is a 5-membered aromatic heteroaryl selected fromwherein the staggered line denotes the attachment point of the Q-substituent to the rest of the molecule; R6a, R6b, R6cand R6dare independently selected from hydrogen, halogen, Ci-Cs-alkyl, Ci- Cs-alkoxy, or Ci-C2-alkylsulfanyl; and R7is hydrogen or Ci-Cs-alkyl.

8. The compound according to any one of claims 1 to 7, wherein R6a, R6b, R6cand R6dare independently selected from hydrogen, halogen, or methyl; and R7is hydrogen or methyl.

9. The compound according to any one of claims 1 to 8, wherein Z1is selected from Ci-Cs-alkyl, wherein said Ci-Cs-alkyl is unsubstituted or substituted with 1 , 2 or 3 substituents independently selected from halogen, cyano, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C2-Cs-alkenyl, C2-Cs-alkynyl, C2-C6- alkenyloxy, C2-Cs-alkynyloxy, Ci-C4-alkylsulfanyl, Ci-C4-alkylsulfonyl, or Cs-Cs-cycloalkyl; and wherein said Cs-Cs-cycloalkyl is unsubstituted or substituted with one substituent selected from halogen, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, or Ci-C4-alkoxy10. The compound according to any one of claims 1 to 9, wherein Z1is selected from Ci-Cs-alkyl, wherein said Ci-Cs-alkyl is unsubstituted or substituted with 1 , 2 or 3 substituents independently selected from halogen, cyano, Ci-C4-alkyl, Ci-C2-alkoxy, Ci-C2-haloalkoxy, C2-C3-alkenyl, C2-C3-alkynyl, C2-C3- alkenyloxy, C2-C3-alkynyloxy, Ci-C2-alkylsulfanyl, Ci-C2-alkylsulfonyl, or cyclopropyl; and wherein said cyclopropyl is unsubstituted or substituted with one substituent selected from halogen, cyano, C1-C3- alkyl, or Ci-C2-haloalkyl.11 . The compound according to any one of claims 1 to 10, wherein Z1is selected from Ci-Cs-alkyl, wherein said Ci-Cs-alkyl is unsubstituted or substituted with 1 , 2 or 3 substituents independently selected from halogen, cyano, Ci-C4-alkyl, Ci-C2-alkoxy, Ci-C2-haloalkoxy, Ci-C2-alkylsulfanyl, Ci-C2-alkylsulfonyl, or cyclopropyl.

12. An agrochemical composition comprising a fungicidally effective amount of a compound of formula (I) as defined in any one of claims 1 to 1 1 .

13. The agrochemical composition according to claim 12, further comprising at least one additional active ingredient and / or an agrochemically-acceptable diluent or carrier.

14. A method of controlling or preventing infestation of useful plants by phytopathogenic microorganisms, wherein a fungicidally effective amount of a compound of formula (I) as defined in any one of claims 1 to 11 , or a composition comprising the compound of formula (I), is applied to the plants, to parts thereof or the locus thereof.

15. Use of a compound according to any one of claims 1 to 11 as a fungicide.

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