Thiobicycle derivatives
Thiobicycle derivatives with specific structural formulas (I) are developed to combat oomycetes, addressing the lack of effective compounds in existing agricultural methods, achieving significant reduction in phytopathogenic infestation and damage.
Patent Information
- Application Number
- PCT/EP2025/057708
- Authority / Receiving Office
- WO · WO
- Patent Type
- Applications
- Current Assignee / Owner
- Priority Date
- 2024-03-20
- Filing Date
- 2025-03-20
- Publication Date
- 2025-09-25
AI Technical Summary
Existing agricultural and horticultural methods lack effective compounds to combat phytopathogenic microorganisms, particularly oomycetes, which cause significant infestation and damage to plants and harvested food crops.
Development of thiobicycle derivatives with specific structural formulas (I) that exhibit microbiocidal activity, particularly fungicidal activity against oomycetes, formulated into agrochemical compositions for direct application to plants or their propagation materials.
The thiobicycle derivatives effectively reduce phytopathogenic infestation and damage by oomycetes, providing a favorable fungicidal effect that enhances plant health and crop yield.
Smart Images

Figure EP2025057708_25092025_PF_FP_ABST
Abstract
Description
[0001] Thiobicycle derivativesThe present invention relates to microbiocidal thiobicycle derivatives, e.g. as active ingredients, whichhave microbiocidal activity, in particular fungicidal activity, more particularly activity against oomycetes.The invention also relates to preparation of these thiobicycle derivatives, to intermediates useful in thepreparation of these thiobicycle derivatives, to the preparation of these intermediates, to agrochemicalcompositions which comprise at least one of the thiobicycle derivatives, to preparation of thesecompositions and to the use of the thiobicycle derivatives or compositions in agriculture or horticulturefor combating, controlling or preventing infestation of plants, harvested food crops, seeds or non-livingmaterials by phytopathogenic microorganisms, in particular fungi, more particularly oomycetes.It has now surprisingly been found that certain novel thiobicycle derivatives have favourable fungicidalproperties, in particular against oomycetes.Therefore, in a first aspect, the present invention provides compounds of formula (I)wherein Z is O or S, A1 is CH or N;A1aare independently CR1or N, with the proviso that no more than one A1ais N, and preferably two A1aare CR1; A1bis CR1or N;R1 are independently selected from hydrogen, halogen, CN, C1-6alkyl, and C3-6cycloalkyl; andpreferably R1 are independently selected from hydrogen and C1-6alkyl;A2are independently CR2or N, with the proviso that no more than three A2are N, preferably no more than two A2are N, preferably no more than one A2is N, and more preferably the four A2are CR2; R2are independently selected from hydrogen, hydroxy, halogen, CN, C1-6alkyl, C1-6alkoxy, C1-6alkoxy- C1-6alkyl, C1-6alkoxy-C1-6alkoxy, C2-6alkenyl, C2-6alkynyl, C3-6cycloalkyl, C3-6cycloalkyl-C1-6alkyl, C1- 6alkylsulfanyl, C1-6alkylsulfinyl, C1-6alkylsulfonyl, C1-6alkoxycarbonyl, C1-6alkylaminocarbonyl, diC1- 6alkylaminocarbonyl, and C1-6alkylcarbonyl, wherein each of the C1-6alkyl, C1-6alkoxy, C1-6alkoxy-C1- 6alkyl, C1-6alkoxy-C1-6alkoxy, C2-6alkenyl, C2-6alkynyl, C3-6cycloalkyl, C3-6cycloalkyl-C1-6alkyl, C1- 6alkylsulfanyl, C1-6alkylsulfinyl, C1-6alkylsulfonyl, C1-6alkoxycarbonyl, C1-6alkylaminocarbonyl, diC1-6alkylaminocarbonyl, and C1-6alkylcarbonyl groups is optionally substituted with one to three substituents independently selected from halogen, hydroxy, and CN; A3is CR3or N; R3is selected from hydrogen, hydroxy, halogen, CN, C1-6alkyl, C1-6alkoxy, C1-6alkoxy-C1-6alkyl, C1- 6alkoxy-C1-6alkoxy, C2-6alkenyl, C2-6alkynyl, C3-6cycloalkyl, C3-6cycloalkyl-C1-6alkyl, C1-6alkylsulfanyl, C1-6alkylsulfinyl, C1-6alkylsulfonyl, C1-6alkoxycarbonyl, amino, C1-6alkylamino, diC1-6-alkylamino, and C3-6cycloalkylamino, wherein each of the C1-6alkyl, C1-6alkoxy, C1-6alkoxy-C1-6alkyl, C1-6alkoxy-C1-6alkoxy, C2-6alkenyl, C2-6alkynyl, C3-6cycloalkyl, C3-6cycloalkyl-C1-6alkyl, C1-6alkylsulfanyl, C1-6alkylsulfinyl, C1-6alkylsulfonyl, C1-6alkoxycarbonyl, amino, C1-6alkylamino, diC1-6-alkylamino, and C3-6cycloalkylaminogroups is optionally substituted with one to three substituents independently selected from halogen, hydroxy, and CN; R4is selected from C1-6alkyl, C1-6alkoxy-C1-6alkyl, C3-6cycloalkyl, C3-6cycloalkyl-C1-4alkyl, C2-6alkenyl, C2- 6alkynyl, C1-6alkoxy, C1-6alkylsulfanyl-C1-6alkyl, C1-6alkylsulfinyl-C1-6alkyl, C1-6alkylsulfonyl-C1-6alkyl, C1-6alkoxycarbonyl-C1-6alkyl, C1-6alkylaminocarbonyl-C1-6alkyl, diC1-6alkylaminocarbonyl-C1-6alkyl, and CN, wherein each of the C1-6alkyl, C1-6alkoxy-C1-6alkyl, C3-6cycloalkyl, C3-6cycloalkyl-C1-4alkyl, C2-6alkenyl, C2- 6alkynyl, C1-6alkoxy, C1-6alkylsulfanyl-C1-6alkyl, C1-6alkylsulfinyl-C1-6alkyl, C1-6alkylsulfonyl-C1-6alkyl, C1- 6alkoxycarbonyl-C1-6alkyl, C1-6alkylaminocarbonyl-C1-6alkyl and diC1-6alkylaminocarbonyl-C1-6alkyl groups is optionally substituted with one to three substituents independently selected from halogen and CN; wherein A3and R4taken together optionally form a ring, preferably a 5-8-membered heterocycle, and more preferably a 6-membered heterocycle; and R5is selected from C1-6alkyl, C1-6alkoxy, C3-6cycloalkyl, C3-6cycloalkyl-C1-6alkyl, C1-6alkoxyC1-6alkyl, C1- 6alkylamino, diC1-6alkylamino, and C1-6alkylC1-6alkoxyamino, wherein each of said groups is optionally substituted with one to three substituents independently selected from halogen and CN; or a salt or N-oxide thereof. In a second aspect the present invention provides an agrochemical composition comprising a compoundof formula (I), and more particularly an agrochemical composition comprising a fungicidally effectiveamount of a compound of formula (I). Said composition can further comprise at least one compound selected among an additional active ingredient, an appropriate formulation inert, a carrier, an adjuvant, and any mixtures thereof. Compounds of formula (I) may be used to control phytopathogenic microorganisms. Thus, in order to control a phytopathogen a compound of formula (I), or a composition comprising a compound of formula(I) according to the invention, may be applied directly to the phytopathogen, to the locus of aphytopathogen, in particular to a plant susceptible to attack by phytopathogens, or to a propagationmaterial of a plant.Thus, in a third aspect the present invention provides the use of a compound of formula (I), or a composition comprising a compound of formula (I), as described herein to combat, prevent or control a phytopathogen.In a fourth aspect the present invention provides a method of combating, preventing or controllingphytopathogens, comprising applying a compound of formula (I), or a composition comprising a compound of formula (I), as described herein to said phytopathogen, to the locus of said phytopathogen, in particular to a plant susceptible to attack by a phytopathogen, or to a propagation material of a plant.According to this fourth aspect of the invention, the method may exclude methods for the treatment ofthe human or animal body by surgery or therapy.Compounds of formula (I) are particularly effective in combating, preventing or controllingphytopathogenic fungi, in particular oomycetes. Thus, in a fifth aspect the present invention providesthe use of a compound of formula (I), or a composition comprising a compound of formula (I), asdescribed herein to control phytopathogenic fungi, in particular oomycetes.In a sixth aspect the present invention provides a method of combating, preventing or controllingphytopathogenic disease, such as phytopathogenic fungi, comprising applying a compound of formula (I), or a composition comprising a compound of formula (I), as described herein to said phytopathogenic fungi, or to the locus of said phytopathogenic fungi, in particular to a plant susceptible to attack byphytopathogenic fungi, in particular oomycetes, or to a propagation material of a plant. According to thissixth aspect of the invention, the method may exclude methods for the treatment of the human or animalbody by surgery or therapy. Where a group is indicated as being substituted, e.g. alkyl, this includes those groups that are part of other groups, e.g. the alkyl in alkylthio. Definitions:- The term "halogen" or “halo” refers to fluorine (fluoro or F), chlorine (chloro or Cl), bromine (bromo orBr) or iodine (iodo or I), preferably fluorine, chlorine or bromine.- The term “amino” refers to a -NH2 group.- The term "alkyl" as used herein- in isolation or as part of a chemical group – represents straight-chainor branched hydrocarbons, preferably with 1 to 6 carbon atoms, for example methyl, ethyl, n-propyl,isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, pentyl, 1- methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,2-dimethylpropyl, 1,1 -dimethylpropyl, 2,2- dimethylpropyl, 1 -ethylpropyl, hexyl, 1 -methylpentyl, 2-methylpentyl, 3-methylpentyl, 4- methylpentyl, 1,2-dimethylpropyl, 1,3-dimethylbutyl, 1,4-dimethylbutyl,2,3-dimethylbutyl, 1,1- dimethylbutyl, 2,2-dimethylbutyl, 3,3-dimethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1- ethylbutyl and 2-ethylbutyl. Alkyl groups with 1 to 4 carbon atoms are preferred, forexample methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl or t-butyl.- The term "Alkenyl" - in isolation or as part of a chemical group - represents straight-chain or branchedhydrocarbons, preferably with 2 to 6 carbon atoms and at least one double bond, for example vinyl, 2-propenyl, 2-butenyl, 3-butenyl, 1- methyl-2-propenyl, 2-methyl-2-propenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-2-butenyl, 2- methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1 - dimethyl-2-propenyl, 1,2-dimethyl-2-propenyl, 1 -ethyl-2-propenyl, 2-hexenyl, 3-hexenyl, 4- hexenyl, 5-hexenyl, 1 -methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2- pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1 -methyl-4-pentenyl, 2-methyl-4-pentenyl, 3- methyl-4-pentenyl, 4-methyl-4-pentenyl, 1, 1 -dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2- dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-2-butenyl, 2,2-dimethyl-3-butenyl,2,3- dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 1 -ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-2-butenyl,2-ethyl-3-butenyl, 1, 1,2-trimethyl-2-propenyl, 1 -ethyl- 1 -methyl-2-propenyl und 1-ethyl-2-methyl-2-propenyl. Alkenyl groups with 2 to 4 carbon atoms are preferred, for example 2-propenyl, 2-butenyl or 1-methyl-2-propenyl.- The term "Alkynyl" - in isolation or as part of a chemical group - represents straight-chain or branchedhydrocarbons, preferably with 2 to 6 carbon atoms and at least one triple bond, for example 2-propynyl,2-butynyl, 3-butynyl, 1-methyl-2- propynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1-methyl-2- butynyl, 1,1 -dimethyl-2-propynyl, 1 -ethyl-2-propynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1- methyl-2-pentynyl, 1-methyl-3-pentynyl, 1 -methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4- pentynyl, 3 -methyl-4-pentynyl, 4-methyl-2-pentynyl, 1,1 -dimethyl-3 -butynyl, 1,2-dimethyl-3 –butynyl, 2,2- dimethyl-3-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl, 1-ethyl-1-methyl-2-propynyl and 2,5-hexadiynyl. Alkynyls with 2 to 4 carbon atoms are preferred, for exampleethynyl, 2- propynyl or 2-butynyl-2-propenyl.- The term "haloalkyl" refers to an alkyl radical as generally defined above substituted by one or moreof the same or different halogen atoms, for examples fluoromethyl, fluoroethyl, difluoromethyl, trifluoromethyl, or 2,2,2-trifluoroethyl.- The term “cyanoalkyl” refers to an alkyl radical as generally defined above substituted by one or morecyano groups.- The term "cycloalkyl" - in isolation or as part of a chemical group - represents saturated or partiallyunsaturated mono-, bi- or tricyclic hydrocarbons, preferably with 3 to 10 carbon atoms, for examplecyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl or adamantyl. Cycloalkyls with 3, 4, 5, 6 or 7 carbon atoms are preferred, for example cyclopropyl or cyclobutyl.- The term “halocycloalkyl" refers to a cycloalkyl ring as defined above substituted by one or more of thesame or different halogen atoms.- The term “cyanocycloalkyl” refers to a cycloalkyl radical as generally defined above substituted by oneor more cyano groups.- The term “alkoxy" refers to a radical of the formula -ORa wherein Ra is an alkyl radical as generallydefined above. Examples of alkoxy include, but are not limited to methoxy, ethoxy, propoxy, iso-propoxy,and tert-butoxy. The term “alkoxyalkyl” refers to an alkyl radical (as mentioned above) substituted withsaid alkoxy group. Examples are methoxymethyl, methoxyethyl, ethoxymethyl and propoxymethyl.- The term “alkylsulfanyl” refers to a radical of the formula -SRa wherein Ra is an alkyl radical as generallydefined above. - The term “alkylsulfinyl” refers to a radical of the formula -S(O)Ra wherein Ra is an alkyl radical as generally defined above.- The term “alkylsulfonyl” refers to a radical of the formula -S(O)2Ra wherein Ra is an alkyl radical asgenerally defined above.- The term “alkylcarbonyl” refers to a radical of the formula RaC(O)- wherein Ra is an alkyl radical asgenerally defined above.- the term “alkoxycarbonyl” refers to a radical of the formula RaOC(O)-, wherein Ra is an alkyl radical asgenerally defined above.- The term “alkylamino” refers to a radical of the formula RaNH- wherein Ra is an alkyl radical as generallydefined above.- The term “cycloalkylamino” refers to a radical of the formula RaNH- wherein Ra is a cycloalkyl radicalas generally defined above.- The term “alkoxyamino” refers to a radical of the formula RaNH-, wherein Ra is an alkoxy radical asgenerally defined above.- The term “alkylaminocarbonyl” refers to a radical of the formula RaNHC(O)- wherein Ra is an alkylradical as generally defined above.- Hydroxyl or hydroxy stands for a –OH group.The term ”combating”, “preventing” or “controlling”, and its inflections, within the context of the presentinvention, mean reducing any undesired effect, such as pathogenic and more particularlyphytopathogenic, especially fungi such as oomycetes, infestation or attack of, and pathogenic damage to a plant or to a plant derived product to such a level that an improvement is demonstrated. As used herein, the term "effective amount" refers to the amount of the compound, a salt, or N-oxide thereof, which, upon single or multiple applications provides the desired effect. An effective amount is readily determined by the skilled person in the art, by the use of 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 tobe applied; the pathogen to be controlled & its lifecycle; the particular compound applied; the type ofapplication; and other relevant circumstances. Compounds of formula (I) which have at least one basic centre can form, for example, acid addition salts, for example with strong inorganic acids such as mineral acids, for example perchloric acid, sulfuric acid, nitric acid, nitrous acid, a phosphorus acid or a hydrohalic acid, with strong organic carboxylic acids, such as C1-4alkanecarboxylic acids which are unsubstituted or substituted, for example by halogen, for example acetic acid, such as saturated or unsaturated dicarboxylic acids, for example oxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid or phthalic acid, such as hydroxycarboxylic acids, for example ascorbic acid, lactic acid, malic acid, tartaric acid or citric acid, or such as benzoicacid, or with organic sulfonic acids, such as C1-4alkane- or arylsulfonic acids which are unsubstituted orsubstituted, for example by halogen, for example methane- or p-toluenesulfonic acid. Compounds offormula (I) which have at least one acidic group can form, for example, salts with bases, for example mineral salts such as alkali metal or alkaline earth metal salts, for example sodium, potassium or magnesium salts, or salts with ammonia or an organic amine, such as morpholine, piperidine,pyrrolidine, a mono-, di- or tri-lower-alkylamine, for example ethyl-, diethyl-, triethyl- ordimethylpropylamine, or a mono-, di- or trihydroxy-lower-alkylamine, for example mono-, di- ortriethanolamine. 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. The compounds of formula (I) according to the invention also include hydrates, which may be formed during salt formation. The compounds of formula (I) according to the invention also include hydrates which may be formed during the salt formation. In a further embodiment, there is provided a compound of formula (I) according to the present invention,wherein R2 are independently selected from hydrogen, hydroxy, halogen, CN, C1-6alkyl, C1-6alkoxy, C1-6alkoxy-C1-6alkyl, C1-6alkoxy-C1-6alkoxy, C1-6alkoxycarbonyl, C1-6alkylaminocarbonyl, diC1-6alkylaminocarbonyl, and C1-6alkylcarbonyl, wherein each of the C1-6alkyl, C1-6alkoxy, C1-6alkoxy-C1-6alkyl, C1-6alkoxy-C1-6alkoxy, C1-6alkoxycarbonyl, C1-6alkylaminocarbonyl, diC1-6alkylaminocarbonyl,and C1-6alkylcarbonyl groups is optionally substituted with one to three substituents independently selected from halogen, hydroxy, and CN; preferably R2are independently selected from hydrogen, halogen, CN, C1-6alkyl, C1-6alkoxy, C1-6alkoxy-C1-6alkyl, and C1-6alkoxy-C1-6alkoxy, wherein each of the C1-6alkyl, C1-6alkoxy, C1-6alkoxy-C1-6alkyl, and C1-6alkoxy-C1-6alkoxy groups is optionally substituted with one to three substituents independently selected from halogen, hydroxy, and CN; and more preferably R2are independently selected from hydrogen, halogen, CN, C1-6alkyl, and C1-6alkoxy. In a further embodiment, there is provided a compound of formula (I) according to the present invention,wherein R3 is selected from hydrogen, hydroxy, halogen, CN, C1-6alkyl, C1-6alkoxy, C1-6alkoxy-C1-6alkyl,C1-6alkoxy-C1-6alkoxy, C3-6cycloalkyl, C3-6cycloalkyl-C1-6alkyl, C1-6alkoxycarbonyl, amino, C1-6alkylamino, diC1-6-alkylamino, and C3-6cycloalkylamino, wherein each of the C1-6alkyl, C1-6alkoxy, C1-6alkoxy-C1-6alkyl, C1-6alkoxy-C1-6alkoxy, C3-6cycloalkyl, C3-6cycloalkyl-C1-6alkyl, C1-6alkoxycarbonyl, amino, C1-6alkylamino, diC1-6-alkylamino and C3-6cycloalkylamino groups is optionally substituted with one to threesubstituents independently selected from halogen, hydroxy, and CN; and preferably R3is selected from hydrogen, hydroxy, halogen, CN, C1-6alkyl, C1-6alkoxy, C1-6alkoxy-C1-6alkyl, and C1-6alkoxycarbonyl, wherein each of the C1-6alkyl, C1-6alkoxy, C1-6alkoxy-C1-6alkyl, and C1-6alkoxycarbonyl groups is optionally substituted with one to three substituents independently selected from halogen, hydroxy, andCN. In a preferred embodiment, R3 can be hydrogen.In a further embodiment, there is provided a compound of formula (I) according to the present invention, wherein four A2are CR2and A3is N. In a further embodiment, there is provided a compound of formula (I) according to the present invention, wherein preferably the three A2 are CR2 and A3 is CR3. In a further embodiment, there is provided a compound of formula (I) according to the present invention, wherein preferably the three A2 are CR2 and A3 is CR3. In a further embodiment, there is provided a compound of formula (I) according to the present invention,wherein four A2 are CR2 and A3 is CR3, and preferably In the particular embodiment wherein are as defined in the present invention;preferably R2are independently halogen, CN, C1-6alkyl, C1-6alkoxy, C1-6alkoxy-C1-6alkyl, C1-6alkoxy-C1-6alkoxy, C3-6cycloalkyl, C3-6cycloalkyl-C1-6alkyl, C1-6alkoxycarbonyl, C1-6alkylaminocarbonyl, diC1-6alkylaminocarbonyl, and C1-6alkylcarbonyl, wherein each of the C1-6alkyl,C1-6alkoxy, C1-6alkoxy-C1-6alkyl, C1-6alkoxy-C1-6alkoxy, C3-6cycloalkyl, C3-6cycloalkyl-C1-6alkyl, C1-6alkoxycarbonyl, C1-6alkylaminocarbonyl, diC1-6alkylaminocarbonyl, and C1-6alkylcarbonyl groups is optionally substituted with one to three substituents independently selected from halogen, hydroxy, andCN; preferably R2 are independently selected from hydrogen, halogen, CN, C1-6alkyl, C1-6alkoxy, C1-6alkoxy-C1-6alkyl, C1-6alkoxycarbonyl, and C1-6alkoxy-C1-6alkoxy, wherein each of the C1-6alkyl, C1-6alkoxy, C1-6alkoxy-C1-6alkyl, C1-6alkoxycarbonyl, and C1-6alkoxy-C1-6alkoxy groups is optionallysubstituted with one to three substituents independently selected from halogen, hydroxy, and CN; and more preferably R2are independently selected from hydrogen, halogen, CN, C1-6alkyl, and C1-6alkoxy. In a further embodiment, there is provided a compound of formula (I) according to the present invention,wherein R4 is selected from C1-6alkyl, C1-6alkoxy-C1-6alkyl, C3-6cycloalkyl, C3-6cycloalkyl-C1-4alkyl, C2-6alkenyl, C2-6alkynyl, and C1-6alkoxy, wherein each of the C1-6alkyl, C1-6alkoxy-C1-6alkyl, C3-6cycloalkyl, C3-6cycloalkyl-C1-4alkyl, C2-6alkenyl, C2-6alkynyl, and C1-6alkoxy groups is optionally substituted with one to three substituents independently selected from halogen and CN; preferably and R4is selected from C1-6alkyl, C1-6alkoxy-C1-6alkyl, C3-6cycloalkyl, C3-6cycloalkyl-C1-4alkyl, and C1-6alkoxy, wherein each of the C1-6alkyl, C1-6alkoxy-C1-6alkyl, C3-6cycloalkyl, C3-6cycloalkyl-C1-4alkyl, and C1-6alkoxy groups is optionally substituted with one to three substituents independently selected from halogen and CN; and wherein A3and R4taken together optionally form a ring, preferably a 5-8-membered heterocycle, and more preferably a 6-membered heterocycle. In a further embodiment, there is provided a compound of formula (I) according to the present invention, wherein A3is CR3and wherein R3and R4taken together form a ring, preferably a 5-8-membered heterocycle, preferably a 6-membered heterocycle, and more preferably one of the rings W1, W2 or W3 as described in the compounds of the formula (I) below:The carbon and / or the nitrogen atoms forming said ring (W1, W2 or W3) can be substituted, especiallyby a R3’ group, wherein R3’ is selected from hydrogen, C1-6alkyl, and C3-6cycloalkyl, wherein each of theC1-6alkyl and C3-6cycloalkyl groups is optionally substituted with one to three substituents independentlyselected from halogen and CN. For example, the compounds of the formula (I-W3) can be as follows: In a preferred embodiment, the compounds of the formula (I-W1), (I-W2) and (I-W3) can be as described below:The carbon and / or the nitrogen atoms forming said ring (W1, W2 or W3) can be substituted, especiallyby a R3’ group, wherein R3’ is selected from hydrogen, C1-6alkyl, and C3-6cycloalkyl, wherein each of theC1-6alkyl and C3-6cycloalkyl groups is optionally substituted with one to three substituents independently selected from halogen and CN. For example, the compounds of the formula (I-W3) can be as follows: In a further embodiment, there is provided a compound of formula (I) according to the present invention,wherein R5 is selected from C1-6alkyl, C1-6alkoxy, C3-6cycloalkyl, C3-6cycloalkyl-C1-6alkyl, and C1-6alkoxyC1-6alkyl, wherein each of said groups is optionally substituted with one to three substituents independently selected from halogen and CN. In a particular embodiment, there is provided a compound of formula (I) according to the present invention, wherein Z is O; A1is CH or N;the two A1a are CR1;A1bis CR1or N;R1 are independently selected from hydrogen, halogen, CN, C1-6alkyl, and C3-6cycloalkyl; andpreferably R1 are independently selected from hydrogen and C1-6alkyl;the four A2 are CR2; with R2 being independently selected from hydrogen, hydroxy, halogen, CN, C1-6alkyl, C1-6alkoxy, C1-6alkoxy-C1-6alkyl, C1-6alkoxy-C1-6alkoxy, C2-6alkenyl, C2-6alkynyl, C3-6cycloalkyl, C3- 6cycloalkyl-C1-6alkyl, C1-6alkylsulfanyl, C1-6alkylsulfinyl, and C1-6alkylsulfonyl, wherein each of the C1- 6alkyl, C1-6alkoxy, C1-6alkoxy-C1-6alkyl, C1-6alkoxy-C1-6alkoxy, C2-6alkenyl, C2-6alkynyl, C3-6cycloalkyl, C3- 6cycloalkyl-C1-6alkyl, C1-6alkylsulfanyl, C1-6alkylsulfinyl and C1-6alkylsulfonyl groups is optionally substituted with one to three substituents independently selected from halogen, hydroxy, and CN;preferably R2 being independently selected from hydrogen, halogen, CN, C1-6alkyl, C1-6alkoxy, C1-6alkoxy-C1-6alkyl, C1-6alkoxycarbonyl, and C1-6alkoxy-C1-6alkoxy, wherein each of the C1-6alkyl, C1-6alkoxy, C1-6alkoxycarbonyl, C1-6alkoxy-C1-6alkyl, and C1-6alkoxy-C1-6alkoxy groups is optionallysubstituted with one to three substituents independently selected from halogen, hydroxy, and CN; andmore preferably R2 being independently selected from hydrogen, halogen, CN, C1-6alkyl, and C1-6alkoxy,wherein each of the C1-6alkyl and C1-6alkoxy groups is optionally substituted with one to threesubstituents independently selected from halogen, hydroxy, and CN; A3is CR3with R3being selected from hydrogen, hydroxy, halogen, CN, C1-6alkyl, C1-6alkoxy, C1-6alkoxy- C1-6alkyl, C1-6alkoxy-C1-6alkoxy, C2-6alkenyl, C2-6alkynyl, C3-6cycloalkyl, C3-6cycloalkyl-C1-6alkyl, C1- 6alkylsulfanyl, C1-6alkylsulfinyl, C1-6alkylsulfonyl, C1-6alkoxycarbonyl, amino, C1-6alkylamino, diC1-6- alkylamino, and C3-6cycloalkylamino, wherein each of the C1-6alkyl, C1-6alkoxy, C1-6alkoxy-C1-6alkyl, C1-6alkoxy-C1-6alkoxy, C2-6alkenyl, C2-6alkynyl, C3-6cycloalkyl, C3-6cycloalkyl-C1-6alkyl, C1-6alkylsulfanyl, C1-6alkylsulfinyl, C1-6alkylsulfonyl, C1-6alkoxycarbonyl, amino, C1-6alkylamino, diC1-6-alkylamino and C3-6cycloalkylamino groups is optionally substituted with one to three substituents independently selectedfrom halogen, hydroxy, and CN; and preferably R3 being hydrogen;R4is selected from C1-6alkyl, C1-6alkoxy-C1-6alkyl, C3-6cycloalkyl, C3-6cycloalkyl-C1-4alkyl, and C1-6alkoxy, wherein each of the C1-6alkyl, C1-6alkoxy-C1-6alkyl, C3-6cycloalkyl, C3-6cycloalkyl-C1-4alkyl, and C1-6alkoxy groups is optionally substituted with one to three substituents independently selected from halogen andCN; and wherein A3 and R4 taken together optionally form a ring, preferably a 5-8-memberedheterocycle, and more preferably a 6-membered heterocycle; andR5is selected from C1-6alkyl, C1-6alkoxy, C3-6cycloalkyl, C3-6cycloalkyl-C1-6alkyl, C1-6alkoxyC1-6 alkyl, C1- 6alkylamino, diC1-6alkylamino, and C1-6alkylC1-6alkoxyamino, wherein each of said groups is optionally substituted with one to three substituents independently selected from halogen and CN, and preferably R5is selected from C1-6alkyl, C1-6alkoxy, C3-6cycloalkyl, C3-6cycloalkyl-C1-6alkyl, and C1-6alkoxyC1-6alkyl, wherein each of said groups is optionally substituted with one to three substituents independently selected from halogen and CN.In a preferred embodiment, wherein R2 are as defined in the present invention;preferably R2are hydroxy, halogen, CN, C1-6alkyl, C1-6alkoxy, C1-6alkoxy-C1-6alkyl, C1-6alkoxy-C1-6alkoxy, C3-6cycloalkyl, C3-6cycloalkyl-C1-6alkyl, C1-6alkoxycarbonyl, C1-6alkylaminocarbonyl, diC1-6alkylaminocarbonyl, and C1-6alkylcarbonyl, wherein each of the C1-6alkyl,C1-6alkoxy, C1-6alkoxy-C1-6alkyl, C1-6alkoxy-C1-6alkoxy, C3-6cycloalkyl, C3-6cycloalkyl-C1-6alkyl, C1-6alkoxycarbonyl, C1-6alkylaminocarbonyl, diC1-6alkylaminocarbonyl, and C1-6alkylcarbonyl groups is optionally substituted with one to three substituents independently selected from halogen, hydroxy, andCN; preferably R2 are independently selected from hydrogen, halogen, CN, C1-6alkyl, C1-6alkoxy, C1-6alkoxy-C1-6alkyl, and C1-6alkoxy-C1-6alkoxy, wherein each of the C1-6alkyl, C1-6alkoxy, C1-6alkoxy-C1- 6alkyl, and C1-6alkoxy-C1-6alkoxy groups is optionally substituted with one to three substituents independently selected from halogen, hydroxy, and CN; and more preferably R2are independently selected from hydrogen, halogen, CN, C1-6alkyl, and C1-6alkoxy. In a further embodiment, the compound according to the present invention is selected from: methyl N-[5-[2-[(4-fluoro-3-methoxy-phenyl)-methyl-carbamoyl]thiazolo[5,4-c]pyridin-7-yl]-2- pyridyl]carbamate; methyl N-[4-[2-[(4-fluoro-3-methoxy-phenyl)-methyl-carbamoyl]thieno[2,3-c]pyridin-4- yl]phenyl]carbamate; methyl N-[5-[2-[(4-cyano-3-methoxy-phenyl)-methyl-carbamoyl]thieno[2,3-c]pyridin-4-yl]-2- pyridyl]carbamate; 4-(6-acetamido-3-pyridyl)-N-(4-fluoro-3-methoxy-phenyl)-N-methyl-thieno[2,3-c]pyridine-2- carboxamide; methyl N-[5-[2-[cyanomethyl-(4-fluoro-3-methoxy-phenyl)carbamoyl]-7-methyl-thieno[2,3-c]pyridin-4- yl]-2-pyridyl]carbamate; methyl N-[5-[2-[(4-fluoro-3-methoxy-phenyl)-methyl-carbamoyl]-7-methyl-thieno[2,3-c]pyridin-4-yl]-2- pyridyl]carbamate; methyl N-[5-[7-chloro-2-[cyanomethyl-(4-fluoro-3-methoxy-phenyl)carbamoyl]thieno[2,3-c]pyridin-4-yl]- 2-pyridyl]carbamate; methyl N-[5-[7-chloro-2-[(4-fluoro-3-methoxy-phenyl)-methyl-carbamoyl]thieno[2,3-c]pyridin-4-yl]-2- pyridyl]carbamate; methyl N-[5-[2-[(4-fluorophenyl)-methyl-carbamoyl]-7-methyl-thieno[2,3-c]pyridin-4-yl]-2- pyridyl]carbamate; methyl N-[5-[7-chloro-2-[(4-fluorophenyl)-methyl-carbamoyl]thieno[2,3-c]pyridin-4-yl]-2- pyridyl]carbamate; methyl N-[5-[2-[cyanomethyl-(4-fluoro-3-methoxy-phenyl)carbamoyl]thieno[2,3-c]pyridin-4-yl]-2- pyridyl]carbamate; methyl N-[5-[2-[(4-fluoro-3-methoxy-phenyl)-methyl-carbamoyl]-3-methyl-thieno[2,3-c]pyridin-4-yl]-2- pyridyl]carbamate; methyl N-[5-[2-[(4-fluorophenyl)-methyl-carbamoyl]-3-methyl-thieno[2,3-c]pyridin-4-yl]-2- pyridyl]carbamate; methyl N-[5-[2-[(4-fluoro-3-methoxy-phenyl)-methyl-carbamoyl]thieno[2,3-c]pyridin-4-yl]-2- pyridyl]carbamate; methyl N-[5-[2-[(4-fluorophenyl)-methyl-carbamoyl]thieno[2,3-c]pyridin-4-yl]-2-pyridyl]carbamate; 7-(4-acetamidophenyl)-N-(4-chlorophenyl)-N-methyl-thiazolo[5,4-c]pyridine-2-carboxamide; methyl N-[4-[2-[(4-chlorophenyl)-methyl-carbamoyl]thiazolo[5,4-c]pyridin-7-yl]phenyl]carbamate; methyl N-[5-[2-[(4-cyano-3-methoxy-phenyl)-methyl-carbamoyl]thiazolo[5,4-c]pyridin-7-yl]-2- pyridyl]carbamate; 4-[6-(ethylcarbamoylamino)-3-pyridyl]-N-(6-methoxy-2-pyridyl)-N-methyl-thieno[2,3-c]pyridine-2- carboxamide; N-(4-cyano-3-fluoro-phenyl)-4-[6-(ethylcarbamoylamino)-3-pyridyl]-N-methyl-thieno[2,3-c]pyridine-2- carboxamide; N-(4-cyano-3-methoxy-phenyl)-4-[6-(ethylcarbamoylamino)-3-pyridyl]-N-methyl-thieno[2,3-c]pyridine-2- carboxamide; 4-[6-(ethylcarbamoylamino)-3-pyridyl]-N-(2-methoxy-4-pyridyl)-N-methyl-thieno[2,3-c]pyridine-2- carboxamide; 4-[6-(ethylcarbamoylamino)-3-pyridyl]-N-(4-methoxy-2-pyridyl)-N-methyl-thieno[2,3-c]pyridine-2- carboxamide; N-(4-chloro-3-fluoro-phenyl)-4-[6-(ethylcarbamoylamino)-3-pyridyl]-N-methyl-thieno[2,3-c]pyridine-2- carboxamide; 4-[4-[(2-methoxyacetyl)amino]phenyl]-N-(6-methoxy-2-pyridyl)-N-methyl-thieno[2,3-c]pyridine-2- carboxamide; N-(4-cyano-3-fluoro-phenyl)-4-[4-[(2-methoxyacetyl)amino]phenyl]-N-methyl-thieno[2,3-c]pyridine-2- carboxamide; N-(4-cyano-3-methoxy-phenyl)-4-[4-[(2-methoxyacetyl)amino]phenyl]-N-methyl-thieno[2,3-c]pyridine-2- carboxamide; 4-[4-[(2-methoxyacetyl)amino]phenyl]-N-(2-methoxy-4-pyridyl)-N-methyl-thieno[2,3-c]pyridine-2- carboxamide; 4-[4-[(2-methoxyacetyl)amino]phenyl]-N-(4-methoxy-2-pyridyl)-N-methyl-thieno[2,3-c]pyridine-2- carboxamide; N-(4-chloro-3-fluoro-phenyl)-4-[4-[(2-methoxyacetyl)amino]phenyl]-N-methyl-thieno[2,3-c]pyridine-2- carboxamide; 4-(4-acetamidophenyl)-N-(6-methoxy-2-pyridyl)-N-methyl-thieno[2,3-c]pyridine-2-carboxamide; 4-(4-acetamidophenyl)-N-(4-cyano-3-fluoro-phenyl)-N-methyl-thieno[2,3-c]pyridine-2-carboxamide; 4-(4-acetamidophenyl)-N-(4-cyano-3-methoxy-phenyl)-N-methyl-thieno[2,3-c]pyridine-2-carboxamide; 4-(4-acetamidophenyl)-N-(2-methoxy-4-pyridyl)-N-methyl-thieno[2,3-c]pyridine-2-carboxamide; 4-(6-acetamido-3-pyridyl)-N-(6-methoxy-2-pyridyl)-N-methyl-thieno[2,3-c]pyridine-2-carboxamide; 4-(6-acetamido-3-pyridyl)-N-(4-cyano-3-fluoro-phenyl)-N-methyl-thieno[2,3-c]pyridine-2-carboxamide; 4-(6-acetamido-3-pyridyl)-N-(2-methoxy-4-pyridyl)-N-methyl-thieno[2,3-c]pyridine-2-carboxamide; methyl N-[5-[2-[(6-methoxy-2-pyridyl)-methyl-carbamoyl]thieno[2,3-c]pyridin-4-yl]-2-pyridyl]carbamate; methyl N-[5-[2-[(4-cyano-3-fluoro-phenyl)-methyl-carbamoyl]thieno[2,3-c]pyridin-4-yl]-2- pyridyl]carbamate; methyl N-[5-[2-[(2-methoxy-4-pyridyl)-methyl-carbamoyl]thieno[2,3-c]pyridin-4-yl]-2-pyridyl]carbamate; and methyl N-[5-[2-[(4-methoxy-2-pyridyl)-methyl-carbamoyl]thieno[2,3-c]pyridin-4-yl]-2-pyridyl]carbamate. The method according to the present invention has advantageous properties for protecting plants against pathogenic, such as phytopathogenic, especially fungi such as oomycetes, attack or infestation, which result in a disease and damage to the plant; particularly in instance of plants, the present invention can control, limit or prevent pathogenic damage on plant, parts of plant, plant propagation material and / or plant grown.The compounds in Tables 1.1 to 1.200 below illustrate specific compounds of the invention.Table 1.1 provides compounds E1.1 to E1.1135 of formula (Ia) are as defined in table Z. Moreparticularly, table Z also includes compounds wherein R3and R4taken together form a ring. In this case,said ring is depicted in the A3 and R4 columns (table Z) merged together, along the amide atom linkedto the bicycle core of the formula (Ia). For example, see the A3and R4columns of the compound E1.133. Table Z: Substituent definitions of R1, A3, R4, A2aand A2b: Compounds A3 R4 A2a A2b R1E1.1 CH CH3 N CH CH3E1.2 CH CH3 CH CH CH3E1.3 CH CH3 CH N CH3E1.4 CH CH3 CF CH CH3E1.5 CH CH3 CF N CH3Compounds A3 R4 A2a A2b R1E1.6 CH CH3 CCl CH CH3E1.7 CH CH3 CCl N CH3E1.8 CH CH3 CBr CH CH3E1.9 CH CH3 CBr N CH3E1.10 CH CH3 CCH3 CH CH3E1.11 CH CH3 CCH3 N CH3E1.12 CH CH3 CCH2CH3 CH CH3E1.13 CH CH3 CCH2CH3 N CH3E1.14 CH CH3 CCN CH CH3E1.15 CH CH3 CCN N CH3E1.16 CH CH2CH3 N CH CH3E1.17 CH CH2CH3 CH CH CH3E1.18 CH CH2CH3 CH N CH3E1.19 CH CH2CH3 CF CH CH3E1.20 CH CH2CH3 CF N CH3E1.21 CH CH2CH3 CCl CH CH3E1.22 CH CH2CH3 CCl N CH3E1.23 CH CH2CH3 CBr CH CH3E1.24 CH CH2CH3 CBr N CH3E1.25 CH CH2CH3 CCH3 CH CH3E1.26 CH CH2CH3 CCH3 N CH3E1.27 CH CH2CH3 CCH2CH3 CH CH3E1.28 CH CH2CH3 CCH2CH3 N CH3E1.29 CH CH2CH3 CCN CH CH3E1.30 CH CH2CH3 CCN N CH3E1.31 CH CH2OCH3 N CH CH3E1.32 CH CH2OCH3 CH CH CH3E1.33 CH CH2OCH3 CH N CH3E1.34 CH CH2OCH3 CF CH CH3E1.35 CH CH2OCH3 CF N CH3E1.36 CH CH2OCH3 CCl CH CH3E1.37 CH CH2OCH3 CCl N CH3E1.38 CH CH2OCH3 CBr CH CH3E1.39 CH CH2OCH3 CBr N CH3E1.40 CH CH2OCH3 CCH3 CH CH3E1.41 CH CH2OCH3 CCH3 N CH3E1.42 CH CH2OCH3 CCH2CH3 CH CH3E1.43 CH CH2OCH3 CCH2CH3 N CH3E1.44 CH CH2OCH3 CCN CH CH3Compounds A3 R4 A2a A2b R1E1.45 CH CH2OCH3 CCN N CH3E1.46 CH CH2CH2OCH3 N CH CH3E1.47 CH CH2CH2OCH3 CH CH CH3E1.48 CH CH2CH2OCH3 CH N CH3E1.49 CH CH2CH2OCH3 CF CH CH3E1.50 CH CH2CH2OCH3 CF N CH3E1.51 CH CH2CH2OCH3 CCl CH CH3E1.52 CH CH2CH2OCH3 CCl N CH3E1.53 CH CH2CH2OCH3 CBr CH CH3E1.54 CH CH2CH2OCH3 CBr N CH3E1.55 CH CH2CH2OCH3 CCH3 CH CH3E1.56 CH CH2CH2OCH3 CCH3 N CH3E1.57 CH CH2CH2OCH3 CCH2CH3 CH CH3E1.58 CH CH2CH2OCH3 CCH2CH3 N CH3E1.59 CH CH2CH2OCH3 CCN CH CH3E1.60 CH CH2CH2OCH3 CCN N CH3E1.61 CH CH2CN N CH CH3E1.62 CH CH2CN CH CH CH3E1.63 CH CH2CN CH N CH3E1.64 CH CH2CN CF CH CH3E1.65 CH CH2CN CF N CH3E1.66 CH CH2CN CCl CH CH3E1.67 CH CH2CN CCl N CH3E1.68 CH CH2CN CBr CH CH3E1.69 CH CH2CN CBr N CH3E1.70 CH CH2CN CCH3 CH CH3E1.71 CH CH2CN CCH3 N CH3E1.72 CH CH2CN CCH2CH3 CH CH3E1.73 CH CH2CN CCH2CH3 N CH3E1.74 CH CH2CN CCN CH CH3E1.75 CH CH2CN CCN N CH3E1.76 CH allyl N CH CH3E1.77 CH allyl CH CH CH3E1.78 CH allyl CH N CH3E1.79 CH allyl CF CH CH3E1.80 CH allyl CF N CH3E1.81 CH allyl CCl CH CH3E1.82 CH allyl CCl N CH3E1.83 CH allyl CBr CH CH3Compounds A3 R4 A2a A2b R1E1.84 CH allyl CBr N CH3E1.85 CH allyl CCH3 CH CH3E1.86 CH allyl CCH3 N CH3E1.87 CH allyl CCH2CH3 CH CH3E1.88 CH allyl CCH2CH3 N CH3E1.89 CH allyl CCN CH CH3E1.90 CH allyl CCN N CH3E1.91 N CH3 CH CH CH3E1.92 N CH3 CF CH CH3E1.93 N CH3 CCl CH CH3E1.94 N CH3 CBr CH CH3E1.95 N CH3 CCH3 CH CH3E1.96 N CH3 CCH2CH3 CH CH3E1.97 N CH3 CCN CH CH3E1.98 N CH2CH3 CH CH CH3E1.99 N CH2CH3 CF CH CH3E1.100 N CH2CH3 CCl CH CH3E1.101 N CH2CH3 CBr CH CH3E1.102 N CH2CH3 CCH3 CH CH3E1.103 N CH2CH3 CCH2CH3 CH CH3E1.104 N CH2CH3 CCN CH CH3E1.105 N CH2OCH3 CH CH CH3E1.106 N CH2OCH3 CF CH CH3E1.107 N CH2OCH3 CCl CH CH3E1.108 N CH2OCH3 CBr CH CH3E1.109 N CH2OCH3 CCH3 CH CH3E1.110 N CH2OCH3 CCH2CH3 CH CH3E1.111 N CH2OCH3 CCN CH CH3E1.112 N CH2CH2OCH3 CH CH CH3E1.113 N CH2CH2OCH3 CF CH CH3E1.114 N CH2CH2OCH3 CCl CH CH3E1.115 N CH2CH2OCH3 CBr CH CH3E1.116 N CH2CH2OCH3 CCH3 CH CH3E1.117 N CH2CH2OCH3 CCH2CH3 CH CH3E1.118 N CH2CH2OCH3 CCN CH CH3E1.119 N CH2CN CH CH CH3E1.120 N CH2CN CF CH CH3E1.121 N CH2CN CCl CH CH3E1.122 N CH2CN CBr CH CH3Compounds A3 R4 A2a A2b R1E1.123 N CH2CN CCH3 CH CH3E1.124 N CH2CN CCH2CH3 CH CH3E1.125 N CH2CN CCN CH CH3E1.126 N allyl CH CH CH3E1.127 N allyl CF CH CH3E1.128 N allyl CCl CH CH3E1.129 N allyl CBr CH CH3E1.130 N allyl CCH3 CH CH3E1.131 N allyl CCH2CH3 CH CH3E1.132 N allyl CCN CH CH3E1.133 N CH CH3E1.134 CH CH CH3E1.135 CH N CH3E1.136 CF CH CH3E1.137 CF N CH3E1.138 CCl CH CH3E1.139 CCl N CH3E1.140 CBr CH CH3E1.141 CBr N CH3Compounds A3 R4 A2a A2b R1E1.142 CCH3 CH CH3E1.143 CCH3 N CH3E1.144 CCH2CH3 CH CH3E1.145 CCH2CH3 N CH3E1.146 CCN CH CH3E1.147 CCN N CH3E1.148 N CH CH3E1.149 CH CH CH3E1.150 CH N CH3E1.151 CF CH CH3E1.152 CF N CH3Compounds A3 R4 A2a A2b R1E1.153 CCl CH CH3E1.154 CCl N CH3E1.155 CBr CH CH3E1.156 CBr N CH3E1.157 CCH3 CH CH3E1.158 CCH3 N CH3E1.159 CCH2CH3 CH CH3E1.160 CCH2CH3 N CH3E1.161 CCN CH CH3E1.162 CCN N CH3E1.163 CH CH3 N CH CH2CH3E1.164 CH CH3 CH CH CH2CH3E1.165 CH CH3 CH N CH2CH3Compounds A3 R4 A2a A2b R1E1.166 CH CH3 CF CH CH2CH3E1.167 CH CH3 CF N CH2CH3E1.168 CH CH3 CCl CH CH2CH3E1.169 CH CH3 CCl N CH2CH3E1.170 CH CH3 CBr CH CH2CH3E1.171 CH CH3 CBr N CH2CH3E1.172 CH CH3 CCH3 CH CH2CH3E1.173 CH CH3 CCH3 N CH2CH3E1.174 CH CH3 CCH2CH3 CH CH2CH3E1.175 CH CH3 CCH2CH3 N CH2CH3E1.176 CH CH3 CCN CH CH2CH3E1.177 CH CH3 CCN N CH2CH3E1.178 CH CH2CH3 N CH CH2CH3E1.179 CH CH2CH3 CH CH CH2CH3E1.180 CH CH2CH3 CH N CH2CH3E1.181 CH CH2CH3 CF CH CH2CH3E1.182 CH CH2CH3 CF N CH2CH3E1.183 CH CH2CH3 CCl CH CH2CH3E1.184 CH CH2CH3 CCl N CH2CH3E1.185 CH CH2CH3 CBr CH CH2CH3E1.186 CH CH2CH3 CBr N CH2CH3E1.187 CH CH2CH3 CCH3 CH CH2CH3E1.188 CH CH2CH3 CCH3 N CH2CH3E1.189 CH CH2CH3 CCH2CH3 CH CH2CH3E1.190 CH CH2CH3 CCH2CH3 N CH2CH3E1.191 CH CH2CH3 CCN CH CH2CH3E1.192 CH CH2CH3 CCN N CH2CH3E1.193 CH CH2OCH3 N CH CH2CH3E1.194 CH CH2OCH3 CH CH CH2CH3E1.195 CH CH2OCH3 CH N CH2CH3E1.196 CH CH2OCH3 CF CH CH2CH3E1.197 CH CH2OCH3 CF N CH2CH3E1.198 CH CH2OCH3 CCl CH CH2CH3E1.199 CH CH2OCH3 CCl N CH2CH3E1.200 CH CH2OCH3 CBr CH CH2CH3E1.201 CH CH2OCH3 CBr N CH2CH3E1.202 CH CH2OCH3 CCH3 CH CH2CH3E1.203 CH CH2OCH3 CCH3 N CH2CH3E1.204 CH CH2OCH3 CCH2CH3 CH CH2CH3Compounds A3 R4 A2a A2b R1E1.205 CH CH2OCH3 CCH2CH3 N CH2CH3E1.206 CH CH2OCH3 CCN CH CH2CH3E1.207 CH CH2OCH3 CCN N CH2CH3E1.208 CH CH2CH2OCH3 N CH CH2CH3E1.209 CH CH2CH2OCH3 CH CH CH2CH3E1.210 CH CH2CH2OCH3 CH N CH2CH3E1.211 CH CH2CH2OCH3 CF CH CH2CH3E1.212 CH CH2CH2OCH3 CF N CH2CH3E1.213 CH CH2CH2OCH3 CCl CH CH2CH3E1.214 CH CH2CH2OCH3 CCl N CH2CH3E1.215 CH CH2CH2OCH3 CBr CH CH2CH3E1.216 CH CH2CH2OCH3 CBr N CH2CH3E1.217 CH CH2CH2OCH3 CCH3 CH CH2CH3E1.218 CH CH2CH2OCH3 CCH3 N CH2CH3E1.219 CH CH2CH2OCH3 CCH2CH3 CH CH2CH3E1.220 CH CH2CH2OCH3 CCH2CH3 N CH2CH3E1.221 CH CH2CH2OCH3 CCN CH CH2CH3E1.222 CH CH2CH2OCH3 CCN N CH2CH3E1.223 CH CH2CN N CH CH2CH3E1.224 CH CH2CN CH CH CH2CH3E1.225 CH CH2CN CH N CH2CH3E1.226 CH CH2CN CF CH CH2CH3E1.227 CH CH2CN CF N CH2CH3E1.228 CH CH2CN CCl CH CH2CH3E1.229 CH CH2CN CCl N CH2CH3E1.230 CH CH2CN CBr CH CH2CH3E1.231 CH CH2CN CBr N CH2CH3E1.232 CH CH2CN CCH3 CH CH2CH3E1.233 CH CH2CN CCH3 N CH2CH3E1.234 CH CH2CN CCH2CH3 CH CH2CH3E1.235 CH CH2CN CCH2CH3 N CH2CH3E1.236 CH CH2CN CCN CH CH2CH3E1.237 CH CH2CN CCN N CH2CH3E1.238 CH allyl N CH CH2CH3E1.239 CH allyl CH CH CH2CH3E1.240 CH allyl CH N CH2CH3E1.241 CH allyl CF CH CH2CH3E1.242 CH allyl CF N CH2CH3E1.243 CH allyl CCl CH CH2CH3Compounds A3 R4 A2a A2b R1E1.244 CH allyl CCl N CH2CH3E1.245 CH allyl CBr CH CH2CH3E1.246 CH allyl CBr N CH2CH3E1.247 CH allyl CCH3 CH CH2CH3E1.248 CH allyl CCH3 N CH2CH3E1.249 CH allyl CCH2CH3 CH CH2CH3E1.250 CH allyl CCH2CH3 N CH2CH3E1.251 CH allyl CCN CH CH2CH3E1.252 CH allyl CCN N CH2CH3E1.253 N CH3 CH CH CH2CH3E1.254 N CH3 CF CH CH2CH3E1.255 N CH3 CCl CH CH2CH3E1.256 N CH3 CBr CH CH2CH3E1.257 N CH3 CCH3 CH CH2CH3E1.258 N CH3 CCH2CH3 CH CH2CH3E1.259 N CH3 CCN CH CH2CH3E1.260 N CH2CH3 CH CH CH2CH3E1.261 N CH2CH3 CF CH CH2CH3E1.262 N CH2CH3 CCl CH CH2CH3E1.263 N CH2CH3 CBr CH CH2CH3E1.264 N CH2CH3 CCH3 CH CH2CH3E1.265 N CH2CH3 CCH2CH3 CH CH2CH3E1.266 N CH2CH3 CCN CH CH2CH3E1.267 N CH2OCH3 CH CH CH2CH3E1.268 N CH2OCH3 CF CH CH2CH3E1.269 N CH2OCH3 CCl CH CH2CH3E1.270 N CH2OCH3 CBr CH CH2CH3E1.271 N CH2OCH3 CCH3 CH CH2CH3E1.272 N CH2OCH3 CCH2CH3 CH CH2CH3E1.273 N CH2OCH3 CCN CH CH2CH3E1.274 N CH2CH2OCH3 CH CH CH2CH3E1.275 N CH2CH2OCH3 CF CH CH2CH3E1.276 N CH2CH2OCH3 CCl CH CH2CH3E1.277 N CH2CH2OCH3 CBr CH CH2CH3E1.278 N CH2CH2OCH3 CCH3 CH CH2CH3E1.279 N CH2CH2OCH3 CCH2CH3 CH CH2CH3E1.280 N CH2CH2OCH3 CCN CH CH2CH3E1.281 N CH2CN CH CH CH2CH3E1.282 N CH2CN CF CH CH2CH3Compounds A3 R4 A2a A2b R1E1.283 N CH2CN CCl CH CH2CH3E1.284 N CH2CN CBr CH CH2CH3E1.285 N CH2CN CCH3 CH CH2CH3E1.286 N CH2CN CCH2CH3 CH CH2CH3E1.287 N CH2CN CCN CH CH2CH3E1.288 N allyl CH CH CH2CH3E1.289 N allyl CF CH CH2CH3E1.290 N allyl CCl CH CH2CH3E1.291 N allyl CBr CH CH2CH3E1.292 N allyl CCH3 CH CH2CH3E1.293 N allyl CCH2CH3 CH CH2CH3E1.294 N allyl CCN CH CH2CH3E1.295 N CH CH2CH3E1.296 CH CH CH2CH3E1.297 CH N CH2CH3E1.298 CF CH CH2CH3E1.299 CF N CH2CH3E1.300 CCl CH CH2CH3E1.301 CCl N CH2CH3E1.302 CBr CH CH2CH3E1.303 CBr N CH2CH3Compounds A3 R4 A2a A2b R1E1.304 CCH3 CH CH2CH3E1.305 CCH3 N CH2CH3E1.306 CCH2CH3 CH CH2CH3E1.307 CCH2CH3 N CH2CH3E1.308 CCN CH CH2CH3E1.309 CCN N CH2CH3E1.310 N CH CH2CH3E1.311 CH CH CH2CH3E1.312 CH N CH2CH3E1.313 CF CH CH2CH3E1.314 CF N CH2CH3Compounds A3 R4 A2a A2b R1E1.315 CCl CH CH2CH3E1.316 CCl N CH2CH3E1.317 CBr CH CH2CH3E1.318 CBr N CH2CH3E1.319 CCH3 CH CH2CH3E1.320 CCH3 N CH2CH3E1.321 CCH2CH3 CH CH2CH3E1.322 CCH2CH3 N CH2CH3E1.323 CCN CH CH2CH3E1.324 CCN N CH2CH3E1.325 CH CH3 N CH CH2OCH3E1.326 CH CH3 CH CH CH2OCH3E1.327 CH CH3 CH N CH2OCH3Compounds A3 R4 A2a A2b R1E1.328 CH CH3 CF CH CH2OCH3E1.329 CH CH3 CF N CH2OCH3E1.330 CH CH3 CCl CH CH2OCH3E1.331 CH CH3 CCl N CH2OCH3E1.332 CH CH3 CBr CH CH2OCH3E1.333 CH CH3 CBr N CH2OCH3E1.334 CH CH3 CCH3 CH CH2OCH3E1.335 CH CH3 CCH3 N CH2OCH3E1.336 CH CH3 CCH2CH3 CH CH2OCH3E1.337 CH CH3 CCH2CH3 N CH2OCH3E1.338 CH CH3 CCN CH CH2OCH3E1.339 CH CH3 CCN N CH2OCH3E1.340 CH CH2CH3 N CH CH2OCH3E1.341 CH CH2CH3 CH CH CH2OCH3E1.342 CH CH2CH3 CH N CH2OCH3E1.343 CH CH2CH3 CF CH CH2OCH3E1.344 CH CH2CH3 CF N CH2OCH3E1.345 CH CH2CH3 CCl CH CH2OCH3E1.346 CH CH2CH3 CCl N CH2OCH3E1.347 CH CH2CH3 CBr CH CH2OCH3E1.348 CH CH2CH3 CBr N CH2OCH3E1.349 CH CH2CH3 CCH3 CH CH2OCH3E1.350 CH CH2CH3 CCH3 N CH2OCH3E1.351 CH CH2CH3 CCH2CH3 CH CH2OCH3E1.352 CH CH2CH3 CCH2CH3 N CH2OCH3E1.353 CH CH2CH3 CCN CH CH2OCH3E1.354 CH CH2CH3 CCN N CH2OCH3E1.355 CH CH2OCH3 N CH CH2OCH3E1.356 CH CH2OCH3 CH CH CH2OCH3E1.357 CH CH2OCH3 CH N CH2OCH3E1.358 CH CH2OCH3 CF CH CH2OCH3E1.359 CH CH2OCH3 CF N CH2OCH3E1.360 CH CH2OCH3 CCl CH CH2OCH3E1.361 CH CH2OCH3 CCl N CH2OCH3E1.362 CH CH2OCH3 CBr CH CH2OCH3E1.363 CH CH2OCH3 CBr N CH2OCH3E1.364 CH CH2OCH3 CCH3 CH CH2OCH3E1.365 CH CH2OCH3 CCH3 N CH2OCH3E1.366 CH CH2OCH3 CCH2CH3 CH CH2OCH3Compounds A3 R4 A2a A2b R1E1.367 CH CH2OCH3 CCH2CH3 N CH2OCH3E1.368 CH CH2OCH3 CCN CH CH2OCH3E1.369 CH CH2OCH3 CCN N CH2OCH3E1.370 CH CH2CH2OCH3 N CH CH2OCH3E1.371 CH CH2CH2OCH3 CH CH CH2OCH3E1.372 CH CH2CH2OCH3 CH N CH2OCH3E1.373 CH CH2CH2OCH3 CF CH CH2OCH3E1.374 CH CH2CH2OCH3 CF N CH2OCH3E1.375 CH CH2CH2OCH3 CCl CH CH2OCH3E1.376 CH CH2CH2OCH3 CCl N CH2OCH3E1.377 CH CH2CH2OCH3 CBr CH CH2OCH3E1.378 CH CH2CH2OCH3 CBr N CH2OCH3E1.379 CH CH2CH2OCH3 CCH3 CH CH2OCH3E1.380 CH CH2CH2OCH3 CCH3 N CH2OCH3E1.381 CH CH2CH2OCH3 CCH2CH3 CH CH2OCH3E1.382 CH CH2CH2OCH3 CCH2CH3 N CH2OCH3E1.383 CH CH2CH2OCH3 CCN CH CH2OCH3E1.384 CH CH2CH2OCH3 CCN N CH2OCH3E1.385 CH CH2CN N CH CH2OCH3E1.386 CH CH2CN CH CH CH2OCH3E1.387 CH CH2CN CH N CH2OCH3E1.388 CH CH2CN CF CH CH2OCH3E1.389 CH CH2CN CF N CH2OCH3E1.390 CH CH2CN CCl CH CH2OCH3E1.391 CH CH2CN CCl N CH2OCH3E1.392 CH CH2CN CBr CH CH2OCH3E1.393 CH CH2CN CBr N CH2OCH3E1.394 CH CH2CN CCH3 CH CH2OCH3E1.395 CH CH2CN CCH3 N CH2OCH3E1.396 CH CH2CN CCH2CH3 CH CH2OCH3E1.397 CH CH2CN CCH2CH3 N CH2OCH3E1.398 CH CH2CN CCN CH CH2OCH3E1.399 CH CH2CN CCN N CH2OCH3E1.400 CH allyl N CH CH2OCH3E1.401 CH allyl CH CH CH2OCH3E1.402 CH allyl CH N CH2OCH3E1.403 CH allyl CF CH CH2OCH3E1.404 CH allyl CF N CH2OCH3E1.405 CH allyl CCl CH CH2OCH3Compounds A3 R4 A2a A2b R1E1.406 CH allyl CCl N CH2OCH3E1.407 CH allyl CBr CH CH2OCH3E1.408 CH allyl CBr N CH2OCH3E1.409 CH allyl CCH3 CH CH2OCH3E1.410 CH allyl CCH3 N CH2OCH3E1.411 CH allyl CCH2CH3 CH CH2OCH3E1.412 CH allyl CCH2CH3 N CH2OCH3E1.413 CH allyl CCN CH CH2OCH3E1.414 CH allyl CCN N CH2OCH3E1.415 N CH3 CH CH CH2OCH3E1.416 N CH3 CF CH CH2OCH3E1.417 N CH3 CCl CH CH2OCH3E1.418 N CH3 CBr CH CH2OCH3E1.419 N CH3 CCH3 CH CH2OCH3E1.420 N CH3 CCH2CH3 CH CH2OCH3E1.421 N CH3 CCN CH CH2OCH3E1.422 N CH2CH3 CH CH CH2OCH3E1.423 N CH2CH3 CF CH CH2OCH3E1.424 N CH2CH3 CCl CH CH2OCH3E1.425 N CH2CH3 CBr CH CH2OCH3E1.426 N CH2CH3 CCH3 CH CH2OCH3E1.427 N CH2CH3 CCH2CH3 CH CH2OCH3E1.428 N CH2CH3 CCN CH CH2OCH3E1.429 N CH2OCH3 CH CH CH2OCH3E1.430 N CH2OCH3 CF CH CH2OCH3E1.431 N CH2OCH3 CCl CH CH2OCH3E1.432 N CH2OCH3 CBr CH CH2OCH3E1.433 N CH2OCH3 CCH3 CH CH2OCH3E1.434 N CH2OCH3 CCH2CH3 CH CH2OCH3E1.435 N CH2OCH3 CCN CH CH2OCH3E1.436 N CH2CH2OCH3 CH CH CH2OCH3E1.437 N CH2CH2OCH3 CF CH CH2OCH3E1.438 N CH2CH2OCH3 CCl CH CH2OCH3E1.439 N CH2CH2OCH3 CBr CH CH2OCH3E1.440 N CH2CH2OCH3 CCH3 CH CH2OCH3E1.441 N CH2CH2OCH3 CCH2CH3 CH CH2OCH3E1.442 N CH2CH2OCH3 CCN CH CH2OCH3E1.443 N CH2CN CH CH CH2OCH3E1.444 N CH2CN CF CH CH2OCH3Compounds A3 R4 A2a A2b R1E1.445 N CH2CN CCl CH CH2OCH3E1.446 N CH2CN CBr CH CH2OCH3E1.447 N CH2CN CCH3 CH CH2OCH3E1.448 N CH2CN CCH2CH3 CH CH2OCH3E1.449 N CH2CN CCN CH CH2OCH3E1.450 N allyl CH CH CH2OCH3E1.451 N allyl CF CH CH2OCH3E1.452 N allyl CCl CH CH2OCH3E1.453 N allyl CBr CH CH2OCH3E1.454 N allyl CCH3 CH CH2OCH3E1.455 N allyl CCH2CH3 CH CH2OCH3E1.456 N allyl CCN CH CH2OCH3E1.457 N CH CH2OCH3E1.458 CH CH CH2OCH3E1.459 CH N CH2OCH3E1.460 CF CH CH2OCH3E1.461 CF N CH2OCH3E1.462 CCl CH CH2OCH3E1.463 CCl N CH2OCH3E1.464 CBr CH CH2OCH3E1.465 CBr N CH2OCH3Compounds A3 R4 A2a A2b R1E1.466 CCH3 CH CH2OCH3E1.467 CCH3 N CH2OCH3E1.468 CCH2CH3 CH CH2OCH3E1.469 CCH2CH3 N CH2OCH3E1.470 CCN CH CH2OCH3E1.471 CCN N CH2OCH3E1.472 N CH CH2OCH3E1.473 CH CH CH2OCH3E1.474 CH N CH2OCH3E1.475 CF CH CH2OCH3E1.476 CF N CH2OCH3Compounds A3 R4 A2a A2b R1E1.477 CCl CH CH2OCH3E1.478 CCl N CH2OCH3E1.479 CBr CH CH2OCH3E1.480 CBr N CH2OCH3E1.481 CCH3 CH CH2OCH3E1.482 CCH3 N CH2OCH3E1.483 CCH2CH3 CH CH2OCH3E1.484 CCH2CH3 N CH2OCH3E1.485 CCN CH CH2OCH3E1.486 CCN N CH2OCH3E1.487 CH CH3 N CH cyclopropylE1.488 CH CH3 CH CH cyclopropylE1.489 CH CH3 CH N cyclopropylCompounds A3 R4 A2a A2b R1E1.490 CH CH3 CF CH cyclopropylE1.491 CH CH3 CF N cyclopropylE1.492 CH CH3 CCl CH cyclopropylE1.493 CH CH3 CCl N cyclopropylE1.494 CH CH3 CBr CH cyclopropylE1.495 CH CH3 CBr N cyclopropylE1.496 CH CH3 CCH3 CH cyclopropylE1.497 CH CH3 CCH3 N cyclopropylE1.498 CH CH3 CCH2CH3 CH cyclopropylE1.499 CH CH3 CCH2CH3 N cyclopropylE1.500 CH CH3 CCN CH cyclopropylE1.501 CH CH3 CCN N cyclopropylE1.502 CH CH2CH3 N CH cyclopropylE1.503 CH CH2CH3 CH CH cyclopropylE1.504 CH CH2CH3 CH N cyclopropylE1.505 CH CH2CH3 CF CH cyclopropylE1.506 CH CH2CH3 CF N cyclopropylE1.507 CH CH2CH3 CCl CH cyclopropylE1.508 CH CH2CH3 CCl N cyclopropylE1.509 CH CH2CH3 CBr CH cyclopropylE1.510 CH CH2CH3 CBr N cyclopropylE1.511 CH CH2CH3 CCH3 CH cyclopropylE1.512 CH CH2CH3 CCH3 N cyclopropylE1.513 CH CH2CH3 CCH2CH3 CH cyclopropylE1.514 CH CH2CH3 CCH2CH3 N cyclopropylE1.515 CH CH2CH3 CCN CH cyclopropylE1.516 CH CH2CH3 CCN N cyclopropylE1.517 CH CH2OCH3 N CH cyclopropylE1.518 CH CH2OCH3 CH CH cyclopropylE1.519 CH CH2OCH3 CH N cyclopropylE1.520 CH CH2OCH3 CF CH cyclopropylE1.521 CH CH2OCH3 CF N cyclopropylE1.522 CH CH2OCH3 CCl CH cyclopropylE1.523 CH CH2OCH3 CCl N cyclopropylE1.524 CH CH2OCH3 CBr CH cyclopropylE1.525 CH CH2OCH3 CBr N cyclopropylE1.526 CH CH2OCH3 CCH3 CH cyclopropylE1.527 CH CH2OCH3 CCH3 N cyclopropylE1.528 CH CH2OCH3 CCH2CH3 CH cyclopropylCompounds A3 R4 A2a A2b R1E1.529 CH CH2OCH3 CCH2CH3 N cyclopropylE1.530 CH CH2OCH3 CCN CH cyclopropylE1.531 CH CH2OCH3 CCN N cyclopropylE1.532 CH CH2CH2OCH3 N CH cyclopropylE1.533 CH CH2CH2OCH3 CH CH cyclopropylE1.534 CH CH2CH2OCH3 CH N cyclopropylE1.535 CH CH2CH2OCH3 CF CH cyclopropylE1.536 CH CH2CH2OCH3 CF N cyclopropylE1.537 CH CH2CH2OCH3 CCl CH cyclopropylE1.538 CH CH2CH2OCH3 CCl N cyclopropylE1.539 CH CH2CH2OCH3 CBr CH cyclopropylE1.540 CH CH2CH2OCH3 CBr N cyclopropylE1.541 CH CH2CH2OCH3 CCH3 CH cyclopropylE1.542 CH CH2CH2OCH3 CCH3 N cyclopropylE1.543 CH CH2CH2OCH3 CCH2CH3 CH cyclopropylE1.544 CH CH2CH2OCH3 CCH2CH3 N cyclopropylE1.545 CH CH2CH2OCH3 CCN CH cyclopropylE1.546 CH CH2CH2OCH3 CCN N cyclopropylE1.547 CH CH2CN N CH cyclopropylE1.548 CH CH2CN CH CH cyclopropylE1.549 CH CH2CN CH N cyclopropylE1.550 CH CH2CN CF CH cyclopropylE1.551 CH CH2CN CF N cyclopropylE1.552 CH CH2CN CCl CH cyclopropylE1.553 CH CH2CN CCl N cyclopropylE1.554 CH CH2CN CBr CH cyclopropylE1.555 CH CH2CN CBr N cyclopropylE1.556 CH CH2CN CCH3 CH cyclopropylE1.557 CH CH2CN CCH3 N cyclopropylE1.558 CH CH2CN CCH2CH3 CH cyclopropylE1.559 CH CH2CN CCH2CH3 N cyclopropylE1.560 CH CH2CN CCN CH cyclopropylE1.561 CH CH2CN CCN N cyclopropylE1.562 CH allyl N CH cyclopropylE1.563 CH allyl CH CH cyclopropylE1.564 CH allyl CH N cyclopropylE1.565 CH allyl CF CH cyclopropylE1.566 CH allyl CF N cyclopropylE1.567 CH allyl CCl CH cyclopropylCompounds A3 R4 A2a A2b R1E1.568 CH allyl CCl N cyclopropylE1.569 CH allyl CBr CH cyclopropylE1.570 CH allyl CBr N cyclopropylE1.571 CH allyl CCH3 CH cyclopropylE1.572 CH allyl CCH3 N cyclopropylE1.573 CH allyl CCH2CH3 CH cyclopropylE1.574 CH allyl CCH2CH3 N cyclopropylE1.575 CH allyl CCN CH cyclopropylE1.576 CH allyl CCN N cyclopropylE1.577 N CH3 CH CH cyclopropylE1.578 N CH3 CF CH cyclopropylE1.579 N CH3 CCl CH cyclopropylE1.580 N CH3 CBr CH cyclopropylE1.581 N CH3 CCH3 CH cyclopropylE1.582 N CH3 CCH2CH3 CH cyclopropylE1.583 N CH3 CCN CH cyclopropylE1.584 N CH2CH3 CH CH cyclopropylE1.585 N CH2CH3 CF CH cyclopropylE1.586 N CH2CH3 CCl CH cyclopropylE1.587 N CH2CH3 CBr CH cyclopropylE1.588 N CH2CH3 CCH3 CH cyclopropylE1.589 N CH2CH3 CCH2CH3 CH cyclopropylE1.590 N CH2CH3 CCN CH cyclopropylE1.591 N CH2OCH3 CH CH cyclopropylE1.592 N CH2OCH3 CF CH cyclopropylE1.593 N CH2OCH3 CCl CH cyclopropylE1.594 N CH2OCH3 CBr CH cyclopropylE1.595 N CH2OCH3 CCH3 CH cyclopropylE1.596 N CH2OCH3 CCH2CH3 CH cyclopropylE1.597 N CH2OCH3 CCN CH cyclopropylE1.598 N CH2CH2OCH3 CH CH cyclopropylE1.599 N CH2CH2OCH3 CF CH cyclopropylE1.600 N CH2CH2OCH3 CCl CH cyclopropylE1.601 N CH2CH2OCH3 CBr CH cyclopropylE1.602 N CH2CH2OCH3 CCH3 CH cyclopropylE1.603 N CH2CH2OCH3 CCH2CH3 CH cyclopropylE1.604 N CH2CH2OCH3 CCN CH cyclopropylE1.605 N CH2CN CH CH cyclopropylE1.606 N CH2CN CF CH cyclopropylCompounds A3 R4 A2a A2b R1E1.607 N CH2CN CCl CH cyclopropylE1.608 N CH2CN CBr CH cyclopropylE1.609 N CH2CN CCH3 CH cyclopropylE1.610 N CH2CN CCH2CH3 CH cyclopropylE1.611 N CH2CN CCN CH cyclopropylE1.612 N allyl CH CH cyclopropylE1.613 N allyl CF CH cyclopropylE1.614 N allyl CCl CH cyclopropylE1.615 N allyl CBr CH cyclopropylE1.616 N allyl CCH3 CH cyclopropylE1.617 N allyl CCH2CH3 CH cyclopropylE1.618 N allyl CCN CH cyclopropylE1.619 N CH cyclopropylE1.620 CH CH cyclopropylE1.621 CH N cyclopropylE1.622 CF CH cyclopropylE1.623 CF N cyclopropylE1.624 CCl CH cyclopropylE1.625 CCl N cyclopropylE1.626 CBr CH cyclopropylE1.627 CBr N cyclopropylCompounds A3 R4 A2a A2b R1E1.628 CCH3 CH cyclopropylE1.629 CCH3 N cyclopropylE1.630 CCH2CH3 CH cyclopropylE1.631 CCH2CH3 N cyclopropylE1.632 CCN CH cyclopropylE1.633 CCN N cyclopropylE1.634 N CH cyclopropylE1.635 CH CH cyclopropylE1.636 CH N cyclopropylE1.637 CF CH cyclopropylE1.638 CF N cyclopropylCompounds A3 R4 A2a A2b R1E1.639 CCl CH cyclopropylE1.640 CCl N cyclopropylE1.641 CBr CH cyclopropylE1.642 CBr N cyclopropylE1.643 CCH3 CH cyclopropylE1.644 CCH3 N cyclopropylE1.645 CCH2CH3 CH cyclopropylE1.646 CCH2CH3 N cyclopropylE1.647 CCN CH cyclopropylE1.648 CCN N cyclopropylE1.649 CH CH3 N CH NHAcE1.650 CH CH3 CH CH NHAcE1.651 CH CH3 CH N NHAcCompounds A3 R4 A2a A2b R1E1.652 CH CH3 CF CH NHAcE1.653 CH CH3 CF N NHAcE1.654 CH CH3 CCl CH NHAcE1.655 CH CH3 CCl N NHAcE1.656 CH CH3 CBr CH NHAcE1.657 CH CH3 CBr N NHAcE1.658 CH CH3 CCH3 CH NHAcE1.659 CH CH3 CCH3 N NHAcE1.660 CH CH3 CCH2CH3 CH NHAcE1.661 CH CH3 CCH2CH3 N NHAcE1.662 CH CH3 CCN CH NHAcE1.663 CH CH3 CCN N NHAcE1.664 CH CH2CH3 N CH NHAcE1.665 CH CH2CH3 CH CH NHAcE1.666 CH CH2CH3 CH N NHAcE1.667 CH CH2CH3 CF CH NHAcE1.668 CH CH2CH3 CF N NHAcE1.669 CH CH2CH3 CCl CH NHAcE1.670 CH CH2CH3 CCl N NHAcE1.671 CH CH2CH3 CBr CH NHAcE1.672 CH CH2CH3 CBr N NHAcE1.673 CH CH2CH3 CCH3 CH NHAcE1.674 CH CH2CH3 CCH3 N NHAcE1.675 CH CH2CH3 CCH2CH3 CH NHAcE1.676 CH CH2CH3 CCH2CH3 N NHAcE1.677 CH CH2CH3 CCN CH NHAcE1.678 CH CH2CH3 CCN N NHAcE1.679 CH CH2OCH3 N CH NHAcE1.680 CH CH2OCH3 CH CH NHAcE1.681 CH CH2OCH3 CH N NHAcE1.682 CH CH2OCH3 CF CH NHAcE1.683 CH CH2OCH3 CF N NHAcE1.684 CH CH2OCH3 CCl CH NHAcE1.685 CH CH2OCH3 CCl N NHAcE1.686 CH CH2OCH3 CBr CH NHAcE1.687 CH CH2OCH3 CBr N NHAcE1.688 CH CH2OCH3 CCH3 CH NHAcE1.689 CH CH2OCH3 CCH3 N NHAcE1.690 CH CH2OCH3 CCH2CH3 CH NHAcCompounds A3 R4 A2a A2b R1E1.691 CH CH2OCH3 CCH2CH3 N NHAcE1.692 CH CH2OCH3 CCN CH NHAcE1.693 CH CH2OCH3 CCN N NHAcE1.694 CH CH2CH2OCH3 N CH NHAcE1.695 CH CH2CH2OCH3 CH CH NHAcE1.696 CH CH2CH2OCH3 CH N NHAcE1.697 CH CH2CH2OCH3 CF CH NHAcE1.698 CH CH2CH2OCH3 CF N NHAcE1.699 CH CH2CH2OCH3 CCl CH NHAcE1.700 CH CH2CH2OCH3 CCl N NHAcE1.701 CH CH2CH2OCH3 CBr CH NHAcE1.702 CH CH2CH2OCH3 CBr N NHAcE1.703 CH CH2CH2OCH3 CCH3 CH NHAcE1.704 CH CH2CH2OCH3 CCH3 N NHAcE1.705 CH CH2CH2OCH3 CCH2CH3 CH NHAcE1.706 CH CH2CH2OCH3 CCH2CH3 N NHAcE1.707 CH CH2CH2OCH3 CCN CH NHAcE1.708 CH CH2CH2OCH3 CCN N NHAcE1.709 CH CH2CN N CH NHAcE1.710 CH CH2CN CH CH NHAcE1.711 CH CH2CN CH N NHAcE1.712 CH CH2CN CF CH NHAcE1.713 CH CH2CN CF N NHAcE1.714 CH CH2CN CCl CH NHAcE1.715 CH CH2CN CCl N NHAcE1.716 CH CH2CN CBr CH NHAcE1.717 CH CH2CN CBr N NHAcE1.718 CH CH2CN CCH3 CH NHAcE1.719 CH CH2CN CCH3 N NHAcE1.720 CH CH2CN CCH2CH3 CH NHAcE1.721 CH CH2CN CCH2CH3 N NHAcE1.722 CH CH2CN CCN CH NHAcE1.723 CH CH2CN CCN N NHAcE1.724 CH allyl N CH NHAcE1.725 CH allyl CH CH NHAcE1.726 CH allyl CH N NHAcE1.727 CH allyl CF CH NHAcE1.728 CH allyl CF N NHAcE1.729 CH allyl CCl CH NHAcCompounds A3 R4 A2a A2b R1E1.730 CH allyl CCl N NHAcE1.731 CH allyl CBr CH NHAcE1.732 CH allyl CBr N NHAcE1.733 CH allyl CCH3 CH NHAcE1.734 CH allyl CCH3 N NHAcE1.735 CH allyl CCH2CH3 CH NHAcE1.736 CH allyl CCH2CH3 N NHAcE1.737 CH allyl CCN CH NHAcE1.738 CH allyl CCN N NHAcE1.739 N CH3 CH CH NHAcE1.740 N CH3 CF CH NHAcE1.741 N CH3 CCl CH NHAcE1.742 N CH3 CBr CH NHAcE1.743 N CH3 CCH3 CH NHAcE1.744 N CH3 CCH2CH3 CH NHAcE1.745 N CH3 CCN CH NHAcE1.746 N CH2CH3 CH CH NHAcE1.747 N CH2CH3 CF CH NHAcE1.748 N CH2CH3 CCl CH NHAcE1.749 N CH2CH3 CBr CH NHAcE1.750 N CH2CH3 CCH3 CH NHAcE1.751 N CH2CH3 CCH2CH3 CH NHAcE1.752 N CH2CH3 CCN CH NHAcE1.753 N CH2OCH3 CH CH NHAcE1.754 N CH2OCH3 CF CH NHAcE1.755 N CH2OCH3 CCl CH NHAcE1.756 N CH2OCH3 CBr CH NHAcE1.757 N CH2OCH3 CCH3 CH NHAcE1.758 N CH2OCH3 CCH2CH3 CH NHAcE1.759 N CH2OCH3 CCN CH NHAcE1.760 N CH2CH2OCH3 CH CH NHAcE1.761 N CH2CH2OCH3 CF CH NHAcE1.762 N CH2CH2OCH3 CCl CH NHAcE1.763 N CH2CH2OCH3 CBr CH NHAcE1.764 N CH2CH2OCH3 CCH3 CH NHAcE1.765 N CH2CH2OCH3 CCH2CH3 CH NHAcE1.766 N CH2CH2OCH3 CCN CH NHAcE1.767 N CH2CN CH CH NHAcE1.768 N CH2CN CF CH NHAcCompounds A3 R4 A2a A2b R1E1.769 N CH2CN CCl CH NHAcE1.770 N CH2CN CBr CH NHAcE1.771 N CH2CN CCH3 CH NHAcE1.772 N CH2CN CCH2CH3 CH NHAcE1.773 N CH2CN CCN CH NHAcE1.774 N allyl CH CH NHAcE1.775 N allyl CF CH NHAcE1.776 N allyl CCl CH NHAcE1.777 N allyl CBr CH NHAcE1.778 N allyl CCH3 CH NHAcE1.779 N allyl CCH2CH3 CH NHAcE1.780 N allyl CCN CH NHAcE1.781 N CH NHAcE1.782 CH CH NHAcE1.783 CH N NHAcE1.784 CF CH NHAcE1.785 CF N NHAcE1.786 CCl CH NHAcE1.787 CCl N NHAcE1.788 CBr CH NHAcE1.789 CBr N NHAcCompounds A3 R4 A2a A2b R1E1.790 CCH3 CH NHAcE1.791 CCH3 N NHAcE1.792 CCH2CH3 CH NHAcE1.793 CCH2CH3 N NHAcE1.794 CCN CH NHAcE1.795 CCN N NHAcE1.796 N CH NHAcE1.797 CH CH NHAcE1.798 CH N NHAcE1.799 CF CH NHAcE1.800 CF N NHAcCompounds A3 R4 A2a A2b R1E1.801 CCl CH NHAcE1.802 CCl N NHAcE1.803 CBr CH NHAcE1.804 CBr N NHAcE1.805 CCH3 CH NHAcE1.806 CCH3 N NHAcE1.807 CCH2CH3 CH NHAcE1.808 CCH2CH3 N NHAcE1.809 CCN CH NHAcE1.810 CCN N NHAcE1.811 CH CH3 N CH CNE1.812 CH CH3 CH CH CNE1.813 CH CH3 CH N CNCompounds A3 R4 A2a A2b R1E1.814 CH CH3 CF CH CNE1.815 CH CH3 CF N CNE1.816 CH CH3 CCl CH CNE1.817 CH CH3 CCl N CNE1.818 CH CH3 CBr CH CNE1.819 CH CH3 CBr N CNE1.820 CH CH3 CCH3 CH CNE1.821 CH CH3 CCH3 N CNE1.822 CH CH3 CCH2CH3 CH CNE1.823 CH CH3 CCH2CH3 N CNE1.824 CH CH3 CCN CH CNE1.825 CH CH3 CCN N CNE1.826 CH CH2CH3 N CH CNE1.827 CH CH2CH3 CH CH CNE1.828 CH CH2CH3 CH N CNE1.829 CH CH2CH3 CF CH CNE1.830 CH CH2CH3 CF N CNE1.831 CH CH2CH3 CCl CH CNE1.832 CH CH2CH3 CCl N CNE1.833 CH CH2CH3 CBr CH CNE1.834 CH CH2CH3 CBr N CNE1.835 CH CH2CH3 CCH3 CH CNE1.836 CH CH2CH3 CCH3 N CNE1.837 CH CH2CH3 CCH2CH3 CH CNE1.838 CH CH2CH3 CCH2CH3 N CNE1.839 CH CH2CH3 CCN CH CNE1.840 CH CH2CH3 CCN N CNE1.841 CH CH2OCH3 N CH CNE1.842 CH CH2OCH3 CH CH CNE1.843 CH CH2OCH3 CH N CNE1.844 CH CH2OCH3 CF CH CNE1.845 CH CH2OCH3 CF N CNE1.846 CH CH2OCH3 CCl CH CNE1.847 CH CH2OCH3 CCl N CNE1.848 CH CH2OCH3 CBr CH CNE1.849 CH CH2OCH3 CBr N CNE1.850 CH CH2OCH3 CCH3 CH CNE1.851 CH CH2OCH3 CCH3 N CNE1.852 CH CH2OCH3 CCH2CH3 CH CNCompounds A3 R4 A2a A2b R1E1.853 CH CH2OCH3 CCH2CH3 N CNE1.854 CH CH2OCH3 CCN CH CNE1.855 CH CH2OCH3 CCN N CNE1.856 CH CH2CH2OCH3 N CH CNE1.857 CH CH2CH2OCH3 CH CH CNE1.858 CH CH2CH2OCH3 CH N CNE1.859 CH CH2CH2OCH3 CF CH CNE1.860 CH CH2CH2OCH3 CF N CNE1.861 CH CH2CH2OCH3 CCl CH CNE1.862 CH CH2CH2OCH3 CCl N CNE1.863 CH CH2CH2OCH3 CBr CH CNE1.864 CH CH2CH2OCH3 CBr N CNE1.865 CH CH2CH2OCH3 CCH3 CH CNE1.866 CH CH2CH2OCH3 CCH3 N CNE1.867 CH CH2CH2OCH3 CCH2CH3 CH CNE1.868 CH CH2CH2OCH3 CCH2CH3 N CNE1.869 CH CH2CH2OCH3 CCN CH CNE1.870 CH CH2CH2OCH3 CCN N CNE1.871 CH CH2CN N CH CNE1.872 CH CH2CN CH CH CNE1.873 CH CH2CN CH N CNE1.874 CH CH2CN CF CH CNE1.875 CH CH2CN CF N CNE1.876 CH CH2CN CCl CH CNE1.877 CH CH2CN CCl N CNE1.878 CH CH2CN CBr CH CNE1.879 CH CH2CN CBr N CNE1.880 CH CH2CN CCH3 CH CNE1.881 CH CH2CN CCH3 N CNE1.882 CH CH2CN CCH2CH3 CH CNE1.883 CH CH2CN CCH2CH3 N CNE1.884 CH CH2CN CCN CH CNE1.885 CH CH2CN CCN N CNE1.886 CH allyl N CH CNE1.887 CH allyl CH CH CNE1.888 CH allyl CH N CNE1.889 CH allyl CF CH CNE1.890 CH allyl CF N CNE1.891 CH allyl CCl CH CNCompounds A3 R4 A2a A2b R1E1.892 CH allyl CCl N CNE1.893 CH allyl CBr CH CNE1.894 CH allyl CBr N CNE1.895 CH allyl CCH3 CH CNE1.896 CH allyl CCH3 N CNE1.897 CH allyl CCH2CH3 CH CNE1.898 CH allyl CCH2CH3 N CNE1.899 CH allyl CCN CH CNE1.900 CH allyl CCN N CNE1.901 N CH3 CH CH CNE1.902 N CH3 CF CH CNE1.903 N CH3 CCl CH CNE1.904 N CH3 CBr CH CNE1.905 N CH3 CCH3 CH CNE1.906 N CH3 CCH2CH3 CH CNE1.907 N CH3 CCN CH CNE1.908 N CH2CH3 CH CH CNE1.909 N CH2CH3 CF CH CNE1.910 N CH2CH3 CCl CH CNE1.911 N CH2CH3 CBr CH CNE1.912 N CH2CH3 CCH3 CH CNE1.913 N CH2CH3 CCH2CH3 CH CNE1.914 N CH2CH3 CCN CH CNE1.915 N CH2CH3 COCH3 CH CNE1.916 N CH2OCH3 CH CH CNE1.917 N CH2OCH3 CF CH CNE1.918 N CH2OCH3 CCl CH CNE1.919 N CH2OCH3 CBr CH CNE1.920 N CH2OCH3 CCH3 CH CNE1.921 N CH2OCH3 CCH2CH3 CH CNE1.922 N CH2OCH3 CCN CH CNE1.923 N CH2CH2OCH3 CH CH CNE1.924 N CH2CH2OCH3 CF CH CNE1.925 N CH2CH2OCH3 CCl CH CNE1.926 N CH2CH2OCH3 CBr CH CNE1.927 N CH2CH2OCH3 CCH3 CH CNE1.928 N CH2CH2OCH3 CCH2CH3 CH CNE1.929 N CH2CH2OCH3 CCN CH CNE1.930 N CH2CN CH CH CNCompounds A3 R4 A2a A2b R1E1.931 N CH2CN CF CH CNE1.932 N CH2CN CCl CH CNE1.933 N CH2CN CBr CH CNE1.934 N CH2CN CCH3 CH CNE1.935 N CH2CN CCH2CH3 CH CNE1.936 N CH2CN CCN CH CNE1.937 N allyl CH CH CNE1.938 N allyl CF CH CNE1.939 N allyl CCl CH CNE1.940 N allyl CBr CH CNE1.941 N allyl CCH3 CH CNE1.942 N allyl CCH2CH3 CH CNE1.943 N allyl CCN CH CNE1.944 N CH CNE1.945 CH CH CNE1.946 CH N CNE1.947 CF CH CNE1.948 CF N CNE1.949 CCl CH CNE1.950 CCl N CNE1.951 CBr CH CNCompounds A3 R4 A2a A2b R1E1.952 CBr N CNE1.953 CCH3 CH CNE1.954 CCH3 N CNE1.955 CCH2CH3 CH CNE1.956 CCH2CH3 N CNE1.957 CCN CH CNE1.958 CCN N CNE1.959 N CH CNE1.960 CH CH CNE1.961 CH N CNE1.962 CF CH CNE1.963 CF N CNCompounds A3 R4 A2a A2b R1E1.964 CCl CH CNE1.965 CCl N CNE1.966 CBr CH CNE1.967 CBr N CNE1.968 CCH3 CH CNE1.969 CCH3 N CNE1.970 CCH2CH3 CH CNE1.971 CCH2CH3 N CNE1.972 CCN CH CNE1.973 CCN N CNE1.974 CH CH3 N CH HE1.975 CH CH3 CH CH HCompounds A3 R4 A2a A2b R1E1.976 CH CH3 CH N HE1.977 CH CH3 CF CH HE1.978 CH CH3 CF N HE1.979 CH CH3 CCl CH HE1.980 CH CH3 CCl N HE1.981 CH CH3 CBr CH HE1.982 CH CH3 CBr N HE1.983 CH CH3 CCH3 CH HE1.984 CH CH3 CCH3 N HE1.985 CH CH3 CCH2CH3 CH HE1.986 CH CH3 CCH2CH3 N HE1.987 CH CH3 CCN CH HE1.988 CH CH3 CCN N HE1.989 CH CH2CH3 N CH HE1.990 CH CH2CH3 CH CH HE1.991 CH CH2CH3 CH N HE1.992 CH CH2CH3 CF CH HE1.993 CH CH2CH3 CF N HE1.994 CH CH2CH3 CCl CH HE1.995 CH CH2CH3 CCl N HE1.996 CH CH2CH3 CBr CH HE1.997 CH CH2CH3 CBr N HE1.998 CH CH2CH3 CCH3 CH HE1.999 CH CH2CH3 CCH3 N HE1.1000 CH CH2CH3 CCH2CH3 CH HE1.1001 CH CH2CH3 CCH2CH3 N HE1.1002 CH CH2CH3 CCN CH HE1.1003 CH CH2CH3 CCN N HE1.1004 CH CH2OCH3 N CH HE1.1005 CH CH2OCH3 CH CH HE1.1006 CH CH2OCH3 CH N HE1.1007 CH CH2OCH3 CF CH HE1.1008 CH CH2OCH3 CF N HE1.1009 CH CH2OCH3 CCl CH HCompounds A3 R4 A2a A2b R1E1.1010 CH CH2OCH3 CCl N HE1.1011 CH CH2OCH3 CBr CH HE1.1012 CH CH2OCH3 CBr N HE1.1013 CH CH2OCH3 CCH3 CH HE1.1014 CH CH2OCH3 CCH3 N HE1.1015 CH CH2OCH3 CCH2CH3 CH HE1.1016 CH CH2OCH3 CCH2CH3 N HE1.1017 CH CH2OCH3 CCN CH HE1.1018 CH CH2OCH3 CCN N HE1.1019 CH CH2CH2OCH3 N CH HE1.1020 CH CH2CH2OCH3 CH CH HE1.1021 CH CH2CH2OCH3 CH N HE1.1022 CH CH2CH2OCH3 CF CH HE1.1023 CH CH2CH2OCH3 CF N HE1.1024 CH CH2CH2OCH3 CCl CH HE1.1025 CH CH2CH2OCH3 CCl N HE1.1026 CH CH2CH2OCH3 CBr CH HE1.1027 CH CH2CH2OCH3 CBr N HE1.1028 CH CH2CH2OCH3 CCH3 CH HE1.1029 CH CH2CH2OCH3 CCH3 N HE1.1030 CH CH2CH2OCH3 CCH2CH3 CH HE1.1031 CH CH2CH2OCH3 CCH2CH3 N HE1.1032 CH CH2CH2OCH3 CCN CH HE1.1033 CH CH2CH2OCH3 CCN N HE1.1034 CH CH2CN N CH HE1.1035 CH CH2CN CH CH HE1.1036 CH CH2CN CH N HE1.1037 CH CH2CN CF CH HE1.1038 CH CH2CN CF N HE1.1039 CH CH2CN CCl CH HE1.1040 CH CH2CN CCl N HE1.1041 CH CH2CN CBr CH HE1.1042 CH CH2CN CBr N HE1.1043 CH CH2CN CCH3 CH HCompounds A3 R4 A2a A2b R1E1.1044 CH CH2CN CCH3 N HE1.1045 CH CH2CN CCH2CH3 CH HE1.1046 CH CH2CN CCH2CH3 N HE1.1047 CH CH2CN CCN CH HE1.1048 CH CH2CN CCN N HE1.1049 CH allyl N CH HE1.1050 CH allyl CH CH HE1.1051 CH allyl CH N HE1.1052 CH allyl CF CH HE1.1053 CH allyl CF N HE1.1054 CH allyl CCl CH HE1.1055 CH allyl CCl N HE1.1056 CH allyl CBr CH HE1.1057 CH allyl CBr N HE1.1058 CH allyl CCH3 CH HE1.1059 CH allyl CCH3 N HE1.1060 CH allyl CCH2CH3 CH HE1.1061 CH allyl CCH2CH3 N HE1.1062 CH allyl CCN CH HE1.1063 CH allyl CCN N HE1.1064 N CH3 CH CH HE1.1065 N CH3 CF CH HE1.1066 N CH3 CCl CH HE1.1067 N CH3 CBr CH HE1.1068 N CH3 CCH3 CH HE1.1069 N CH3 CCH2CH3 CH HE1.1070 N CH3 CCN CH HE1.1071 N CH2CH3 CH CH HE1.1072 N CH2CH3 CF CH HE1.1073 N CH2CH3 CCl CH HE1.1074 N CH2CH3 CBr CH HE1.1075 N CH2CH3 CCH3 CH HE1.1076 N CH2CH3 CCH2CH3 CH HE1.1077 N CH2CH3 CCN CH HCompounds A3 R4 A2a A2b R1E1.1078 N CH2OCH3 CH CH HE1.1079 N CH2OCH3 CF CH HE1.1080 N CH2OCH3 CCl CH HE1.1081 N CH2OCH3 CBr CH HE1.1082 N CH2OCH3 CCH3 CH HE1.1083 N CH2OCH3 CCH2CH3 CH HE1.1084 N CH2OCH3 CCN CH HE1.1085 N CH2CH2OCH3 CH CH HE1.1086 N CH2CH2OCH3 CF CH HE1.1087 N CH2CH2OCH3 CCl CH HE1.1088 N CH2CH2OCH3 CBr CH HE1.1089 N CH2CH2OCH3 CCH3 CH HE1.1090 N CH2CH2OCH3 CCH2CH3 CH HE1.1091 N CH2CH2OCH3 CCN CH HE1.1092 N CH2CN CH CH HE1.1093 N CH2CN CF CH HE1.1094 N CH2CN CCl CH HE1.1095 N CH2CN CBr CH HE1.1096 N CH2CN CCH3 CH HE1.1097 N CH2CN CCH2CH3 CH HE1.1098 N CH2CN CCN CH HE1.1099 N allyl CH CH HE1.1100 N allyl CF CH HE1.1101 N allyl CCl CH HE1.1102 N allyl CBr CH HE1.1103 N allyl CCH3 CH HE1.1104 N allyl CCH2CH3 CH HE1.1105 N allyl CCN CH HN CH HE1.1106 CH CH HE1.1107Compounds A3 R4 A2a A2b R1CH N HE1.1108 CF CH HE1.1109 CF N HE1.1110 CCl CH HE1.1111 CCl N HE1.1112 CBr CH HE1.1113 CBr N HE1.1114 CCH3 CH HE1.1115 CCH3 N HE1.1116 CCH2CH3 CH HE1.1117 CCH2CH3 N HE1.1118 CCN CH HE1.1119 CCN N HE1.1120Compounds A3 R4 A2a A2b R1N CH HE1.1121 CH CH HE1.1122 CH N HE1.1123 CF CH HE1.1124 CF N HE1.1125 CCl CH HE1.1126 CCl N HE1.1127 CBr CH HE1.1128 CBr N HE1.1129 CCH3 CH HE1.1130Compounds A3 R4 A2a A2b R1CCH3 N HE1.1131 CCH2CH3 CH HE1.1132 CCH2CH3 N HE1.1133 CCN CH HE1.1134 CCN N HE1.1135Table 1.2 provides compounds E2.1 to E2.1135 of formula (Ia) wherein A1b is CH, R2 is H, A1 is CH, R5is OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.3 provides compounds E3.1 to E3.1135 of formula (Ia) wherein A1b is CH, R2 is H, A1 is CH, R5is cyclopropyl and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.4 provides compounds E4.1 to E4.1135 of formula (Ia) wherein A1b is CH,A1b is CH, R2 is H, A1is CH, R5is CH2OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.5 provides compounds E5.1 to E5.1135 of formula (Ia) wherein A1b is CH,A1b is CH, R2 is H, A1is CH, R5is NHCH2CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.6 provides compounds E6.1 to E6.1135 of formula (Ia) wherein A1b is CH, R2 is H, A1 is N, R5 isCH3 and R1, A3, R4, A2a, A2b are as defined in table Z.Table 1.7 provides compounds E7.1 to E7.1135 of formula (Ia) wherein A1b is CH, R2 is H, A1 is N, R5 isOCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.8 provides compounds E8.1 to E8.1135 of formula (Ia) wherein A1b is CH, R2 is H, A1 is N, R5 iscyclopropyl and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.9 provides compounds E9.1 to E9.1135 of formula (Ia) wherein A1b is CH, R2 is H, A1 is N, R5 isCH2OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.10 provides compounds E10.1 to E10.1135 of formula (Ia) wherein A1b is CH, R2 is H, A1 is N,R5is NHCH2CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.11 provides compounds E11.1 to E11.1135 of formula (Ia) wherein A1b is CH, R2 is CH3, A1 isCH, R5is CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.12 provides compounds E12.1 to E12.1135 of formula (Ia) wherein A1b is CH, R2 is CH3, A1 isCH, R5is OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.13 provides compounds E13.1 to E13.1135 of formula (Ia) wherein A1b is CH, R2 is CH3, A1 isCH, R5is cyclopropyl and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.14 provides compounds E14.1 to E14.1135 of formula (Ia) wherein A1b is CH, R2 is CH3, A1 isCH, R5is CH2OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.15 provides compounds E15.1 to E15.1135 of formula (Ia) wherein A1b is CH, R2 is CH3, A1 isCH, R5is NHCH2CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.16 provides compounds E16.1 to E16.1135 of formula (Ia) wherein A1b is CH, R2 is CH3, A1 isN, R5is CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.17 provides compounds E17.1 to E17.1135 of formula (Ia) wherein A1b is CH, R2 is CH3, A1 isN, R5is OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.18 provides compounds E18.1 to E18.1135 of formula (Ia) wherein A1b is CH, R2 is CH3, A1 isN, R5is cyclopropyl and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.19 provides compounds E19.1 to E19.1135 of formula (Ia) wherein A1b is CH, R2 is CH3, A1 isN, R5is CH2OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.20 provides compounds E20.1 to E20.1135 of formula (Ia) wherein A1b is CH, R2 is CH3, A1 isN, R5is NHCH2CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.21 provides compounds E21.1 to E21.1135 of formula (Ia) wherein A1b is CH, R2 is CH2CH3, A1is CH, R5is CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.22 provides compounds E22.1 to E22.1135 of formula (Ia) wherein A1b is CH, R2 is CH2CH3, A1is CH, R5is OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.23 provides compounds E23.1 to E23.1135 of formula (Ia) wherein A1b is CH, R2 is CH2CH3, A1is CH, R5is cyclopropyl and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.24 provides compounds E24.1 to E24.1135 of formula (Ia) wherein A1b is CH, R2 is CH2CH3, A1is CH, R5is CH2OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.25 provides compounds E25.1 to E25.1135 of formula (Ia) wherein A1b is CH, R2 is CH2CH3, A1is CH, R5is NHCH2CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.26 provides compounds E26.1 to E26.1135 of formula (Ia) wherein A1b is CH, R2 is CH2CH3, A1is N, R5is CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.27 provides compounds E27.1 to E27.1135 of formula (Ia) wherein A1b is CH, R2 is CH2CH3, A1is N, R5is OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.28 provides compounds E28.1 to E28.1135 of formula (Ia) wherein A1b is CH, R2 is CH2CH3, A1is N, R5is cyclopropyl and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.29 provides compounds E29.1 to E29.1135 of formula (Ia) wherein A1b is CH, R2 is CH2CH3, A1is N, R5is CH2OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.30 provides compounds E30.1 to E30.1135 of formula (Ia) wherein A1b is CH, R2 is CH2CH3, A1is N, R5is NHCH2CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.31 provides compounds E31.1 to E31.1135 of formula (Ia) wherein A1b is CH, R2 is F, A1 is CH,R5is CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.32 provides compounds E32.1 to E32.1135 of formula (Ia) wherein A1b is CH, R2 is F, A1 is CH,R5is OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.33 provides compounds E33.1 to E33.1135 of formula (Ia) wherein A1b is CH, R2 is F, A1 is CH,R5is cyclopropyl and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.34 provides compounds E34.1 to E34.1135 of formula (Ia) wherein A1b is CH, R2 is F, A1 is CH,R5is CH2OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.35 provides compounds E35.1 to E35.1135 of formula (Ia) wherein A1b is CH, R2 is F, A1 is CH,R5is NHCH2CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.36 provides compounds E36.1 to E36.1135 of formula (Ia) wherein A1b is CH, R2 is F, A1 is N,R5is CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.37 provides compounds E37.1 to E37.1135 of formula (Ia) wherein A1b is CH, R2 is F, A1 is N,R5is OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.38 provides compounds E38.1 to E38.1135 of formula (Ia) wherein A1b is CH, R2 is F, A1 is N,R5is cyclopropyl and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.39 provides compounds E39.1 to E39.1135 of formula (Ia) wherein A1b is CH, R2 is F, A1 is N,R5is CH2OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.40 provides compounds E40.1 to E40.1135 of formula (Ia) wherein A1b is CH, R2 is F, A1 is N,R5is NHCH2CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.41 provides compounds E41.1 to E41.1135 of formula (Ia) wherein A1b is CH, R2 is Cl, A1 is CH,R5is CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.42 provides compounds E42.1 to E42.1135 of formula (Ia) wherein A1b is CH, R2 is Cl, A1 is CH,R5is OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.43 provides compounds E43.1 to E43.1135 of formula (Ia) wherein A1b is CH, R2 is Cl, A1 is CH,R5is cyclopropyl and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.44 provides compounds E44.1 to E44.1135 of formula (Ia) wherein A1b is CH, R2 is Cl, A1 is CH,R5is CH2OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.45 provides compounds E45.1 to E45.1135 of formula (Ia) wherein A1b is CH, R2 is Cl, A1 is CH,R5is NHCH2CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.46 provides compounds E46.1 to E46.1135 of formula (Ia) wherein A1b is CH, R2 is Cl, A1 is N,R5 is CH3 and R1, A3, R4, A2a, A2b are as defined in table Z.Table 1.47 provides compounds E47.1 to E47.1135 of formula (Ia) wherein A1b is CH, R2 is Cl, A1 is N,R5is OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.48 provides compounds E48.1 to E48.1135 of formula (Ia) wherein A1b is CH, R2 is Cl, A1 is N,R5is cyclopropyl and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.49 provides compounds E49.1 to E49.1135 of formula (Ia) wherein A1b is CH, R2 is Cl, A1 is N,R5is CH2OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.50 provides compounds E50.1 to E50.1135 of formula (Ia) wherein A1b is CH, R2 is Cl, A1 is N,R5is NHCH2CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.51 provides compounds E51.1 to E51.1135 of formula (Ia) wherein A1b is CH, R2 is Br, A1 is CH,R5is CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.52 provides compounds E52.1 to E52.1135 of formula (Ia) wherein A1b is CH, R2 is Br, A1 is CH,R5is OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.53 provides compounds E53.1 to E53.1135 of formula (Ia) wherein A1b is CH, R2 is Br, A1 is CH,R5is cyclopropyl and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.54 provides compounds E54.1 to E54.1135 of formula (Ia) wherein A1b is CH, R2 is Br, A1 is CH,R5is CH2OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.55 provides compounds E55.1 to E55.1135 of formula (Ia) wherein A1b is CH, R2 is Br, A1 is CH,R5is NHCH2CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.56 provides compounds E56.1 to E56.1135 of formula (Ia) wherein A1b is CH, R2 is Br, A1 is N,R5is CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.57 provides compounds E57.1 to E57.1135 of formula (Ia) wherein A1b is CH, R2 is Br, A1 is N,R5is OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.58 provides compounds E58.1 to E58.1135 of formula (Ia) wherein A1b is CH, R2 is Br, A1 is N,R5is cyclopropyl and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.59 provides compounds E59.1 to E59.1135 of formula (Ia) wherein A1b is CH, R2 is Br, A1 is N,R5is CH2OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.60 provides compounds E60.1 to E60.1135 of formula (Ia) wherein A1b is CH, R2 is Br, A1 is N,R5is NHCH2CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.61 provides compounds E61.1 to E61.1135 of formula (Ia) wherein A1b is CH, R2 is CN, A1 isCH, R5is CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.62 provides compounds E62.1 to E62.1135 of formula (Ia) wherein A1b is CH, R2 is CN, A1 isCH, R5is OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.63 provides compounds E63.1 to E63.1135 of formula (Ia) wherein A1b is CH, R2 is CN, A1 isCH, R5is cyclopropyl and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.64 provides compounds E64.1 to E64.1135 of formula (Ia) wherein A1b is CH, R2 is CN, A1 isCH, R5is CH2OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.65 provides compounds E65.1 to E65.1135 of formula (Ia) wherein A1b is CH, R2 is CN, A1 isCH, R5is NHCH2CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.66 provides compounds E66.1 to E66.1135 of formula (Ia) wherein A1b is CH, R2 is CN, A1 is N,R5is CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.67 provides compounds E67.1 to E67.1135 of formula (Ia) wherein A1b is CH, R2 is CN, A1 is N,R5is OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.68 provides compounds E68.1 to E68.1135 of formula (Ia) wherein A1b is CH, R2 is CN, A1 is N,R5is cyclopropyl and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.69 provides compounds E69.1 to E69.1135 of formula (Ia) wherein A1b is CH, R2 is CN, A1 is N,R5is CH2OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.70 provides compounds E70.1 to E70.1135 of formula (Ia) wherein A1b is CH, R2 is CN, A1 is N,R5is NHCH2CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.71 provides compounds E71.1 to E71.1135 of formula (Ia) wherein A1b is CH, R2 is OCH3, A1 isCH, R5is CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.72 provides compounds E72.1 to E72.1135 of formula (Ia) wherein A1b is CH, R2 is OCH3, A1 isCH, R5is OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.73 provides compounds E73.1 to E73.1135 of formula (Ia) wherein A1b is CH, R2 is OCH3, A1 isCH, R5is cyclopropyl and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.74 provides compounds E74.1 to E74.1135 of formula (Ia) wherein A1b is CH, R2 is OCH3, A1 isCH, R5is CH2OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.75 provides compounds E75.1 to E75.1135 of formula (Ia) wherein A1b is CH, R2 is OCH3, A1 isCH, R5is NHCH2CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.76 provides compounds E76.1 to E76.1135 of formula (Ia) wherein A1b is CH, R2 is OCH3, A1 isN, R5is CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.77 provides compounds E77.1 to E77.1135 of formula (Ia) wherein A1b is CH, R2 is OCH3, A1 isN, R5is OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.78 provides compounds E78.1 to E78.1135 of formula (Ia) wherein A1b is CH, R2 is OCH3, A1 isN, R5is cyclopropyl and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.79 provides compounds E79.1 to E79.1135 of formula (Ia) wherein A1b is CH, R2 is OCH3, A1 isN, R5is CH2OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.80 provides compounds E80.1 to E80.1135 of formula (Ia) wherein A1b is CH, R2 is OCH3, A1 isN, R5is NHCH2CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.81 provides compounds E81.1 to E81.1135 of formula (Ia) wherein A1b is CH, R2 is OCH2CH3,A1is CH, R5is CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.82 provides compounds E82.1 to E82.1135 of formula (Ia) wherein A1b is CH, R2 is OCH2CH3,A1is CH, R5is OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.83 provides compounds E83.1 to E83.1135 of formula (Ia) wherein A1b is CH, R2 is OCH2CH3,A1is CH, R5is cyclopropyl and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.84 provides compounds E84.1 to E84.1135 of formula (Ia) wherein A1b is CH, R2 is OCH2CH3,A1is CH, R5is CH2OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.85 provides compounds E85.1 to E85.1135 of formula (Ia) wherein A1b is CH, R2 is OCH2CH3,A1is CH, R5is NHCH2CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.86 provides compounds E86.1 to E86.1135 of formula (Ia) wherein A1b is CH, R2 is OCH2CH3,A1is N, R5is CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.87 provides compounds E87.1 to E87.1135 of formula (Ia) wherein A1b is CH, R2 is OCH2CH3,A1 is N, R5 is OCH3 and R1, A3, R4, A2a, A2b are as defined in table Z.Table 1.88 provides compounds E88.1 to E88.1135 of formula (Ia) wherein A1b is CH, R2 is OCH2CH3,A1is N, R5is cyclopropyl and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.89 provides compounds E89.1 to E89.1135 of formula (Ia) wherein A1b is CH, R2 is OCH2CH3,A1is N, R5is CH2OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.90 provides compounds E90.1 to E90.1135 of formula (Ia) wherein A1b is CH, R2 is OCH2CH3,A1is N, R5is NHCH2CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.91 provides compounds E91.1 to E91.1135 of formula (Ia) wherein A1b is CH, R2 is CO2CH3, A1is CH, R5 is CH3 and R1, A3, R4, A2a, A2b are as defined in table Z.Table 1.92 provides compounds E92.1 to E92.1135 of formula (Ia) wherein A1b is CH, R2 is CO2CH3, A1is CH, R5is OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.93 provides compounds E93.1 to E93.1135 of formula (Ia) wherein A1b is CH, R2 is CO2CH3, A1is CH, R5is cyclopropyl and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.94 provides compounds E94.1 to E94.1135 of formula (Ia) wherein A1b is CH, R2 is CO2CH3, A1is CH, R5is CH2OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.95 provides compounds E95.1 to E95.1135 of formula (Ia) wherein A1b is CH, R2 is CO2CH3, A1is CH, R5is NHCH2CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.96 provides compounds E96.1 to E96.1135 of formula (Ia) wherein A1b is CH, R2 is CO2CH3, A1is N, R5is CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.97 provides compounds E97.1 to E97.1135 of formula (Ia) wherein A1b is CH, R2 is CO2CH3, A1is N, R5is OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.98 provides compounds E98.1 to E98.1135 of formula (Ia) wherein A1b is CH, R2 is CO2CH3, A1is N, R5is cyclopropyl and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.99 provides compounds E99.1 to E99.1135 of formula (Ia) wherein A1b is CH, R2 is CO2CH3, A1is N, R5is CH2OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.100 provides compounds E100.1 to E100.1135 of formula (Ia) wherein A1b is CH, R2 is CO2CH3,A1is N, R5is NHCH2CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.101 provides compounds E101.1 to E101.1135 of formula (Ia) wherein A1b is N, R2 is H, A1 isCH, R5is CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.102 provides compounds E102.1 to E102.1135 of formula (Ia) wherein A1b is N, R2 is H, A1 isCH, R5is OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.103 provides compounds E103.1 to E103.1135 of formula (Ia) wherein A1b is N, R2 is H, A1 isCH, R5is cyclopropyl and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.104 provides compounds E104.1 to E104.1135 of formula (Ia) wherein A1b is N, R2 is H, A1 isCH, R5is CH2OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.105 provides compounds E105.1 to E105.1135 of formula (Ia) wherein A1b is N, R2 is H, A1 isCH, R5is NHCH2CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.106 provides compounds E106.1 to E106.1135 of formula (Ia) wherein A1b is N, R2 is H, A1 isN, R5is CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.107 provides compounds E107.1 to E107.1135 of formula (Ia) wherein A1b is N, R2 is H, A1 isN, R5is OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.108 provides compounds E108.1 to E108.1135 of formula (Ia) wherein A1b is N, R2 is H, A1 isN, R5is cyclopropyl and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.109 provides compounds E109.1 to E109.1135 of formula (Ia) wherein A1b is N, R2 is H, A1 isN, R5is CH2OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.110 provides compounds E110.1 to E110.1135 of formula (Ia) wherein A1b is N, R2 is H, A1 isN, R5is NHCH2CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.111 provides compounds E111.1 to E111.1135 of formula (Ia) wherein A1b is N, R2 is CH3, A1is CH, R5is CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.112 provides compounds E112.1 to E112.1135 of formula (Ia) wherein A1b is N, R2 is CH3, A1is CH, R5is OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.113 provides compounds E113.1 to E113.1135 of formula (Ia) wherein A1b is N, R2 is CH3, A1is CH, R5is cyclopropyl and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.114 provides compounds E114.1 to E114.1135 of formula (Ia) wherein A1b is N, R2 is CH3, A1is CH, R5is CH2OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.115 provides compounds E115.1 to E115.1135 of formula (Ia) wherein A1b is N, R2 is CH3, A1is CH, R5is NHCH2CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.116 provides compounds E116.1 to E116.1135 of formula (Ia) wherein A1b is N, R2 is CH3, A1is N, R5is CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.117 provides compounds E117.1 to E117.1135 of formula (Ia) wherein A1b is N, R2 is CH3, A1is N, R5is OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.118 provides compounds E118.1 to E118.1135 of formula (Ia) wherein A1b is N, R2 is CH3, A1is N, R5is cyclopropyl and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.119 provides compounds E119.1 to E119.1135 of formula (Ia) wherein A1b is N, R2 is CH3, A1is N, R5is CH2OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.120 provides compounds E120.1 to E120.1135 of formula (Ia) wherein A1b is N, R2 is CH3, A1is N, R5is NHCH2CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.121 provides compounds E121.1 to E121.1135 of formula (Ia) wherein A1b is N, R2 is CH2CH3,A1is CH, R5is CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.122 provides compounds E122.1 to E122.1135 of formula (Ia) wherein A1b is N, R2 is CH2CH3,A1is CH, R5is OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.123 provides compounds E123.1 to E123.1135 of formula (Ia) wherein A1b is N, R2 is CH2CH3,A1is CH, R5is cyclopropyl and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.124 provides compounds E124.1 to E124.1135 of formula (Ia) wherein A1b is N, R2 is CH2CH3,A1is CH, R5is CH2OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.125 provides compounds E125.1 to E125.1135 of formula (Ia) wherein A1b is N, R2 is CH2CH3,A1is CH, R5is NHCH2CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.126 provides compounds E126.1 to E126.1135 of formula (Ia) wherein A1b is N, R2 is CH2CH3,A1is N, R5is CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.127 provides compounds E127.1 to E127.1135 of formula (Ia) wherein A1b is N, R2 is CH2CH3,A1is N, R5is OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.128 provides compounds E128.1 to E128.1135 of formula (Ia) wherein A1b is N, R2 is CH2CH3,A1is N, R5is cyclopropyl and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.129 provides compounds E129.1 to E129.1135 of formula (Ia) wherein A1b is N, R2 is CH2CH3,A1is N, R5is CH2OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.130 provides compounds E130.1 to E130.1135 of formula (Ia) wherein A1b is N, R2 is CH2CH3,A1is N, R5is NHCH2CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.131 provides compounds E131.1 to E131.1135 of formula (Ia) wherein A1b is N, R2 is F, A1 isCH, R5is CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.132 provides compounds E132.1 to E132.1135 of formula (Ia) wherein A1b is N, R2 is F, A1 isCH, R5is OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.133 provides compounds E133.1 to E133.1135 of formula (Ia) wherein A1b is N, R2 is F, A1 isCH, R5is cyclopropyl and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.134 provides compounds E134.1 to E134.1135 of formula (Ia) wherein A1b is N, R2 is F, A1 isCH, R5is CH2OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.135 provides compounds E135.1 to E135.1135 of formula (Ia) wherein A1b is N, R2 is F, A1 isCH, R5is NHCH2CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.136 provides compounds E136.1 to E136.1135 of formula (Ia) wherein A1b is N, R2 is F, A1 isN, R5is CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.137 provides compounds E137.1 to E137.1135 of formula (Ia) wherein A1b is N, R2 is F, A1 isN, R5is OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.138 provides compounds E138.1 to E138.1135 of formula (Ia) wherein A1b is N, R2 is F, A1 isN, R5is cyclopropyl and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.139 provides compounds E139.1 to E139.1135 of formula (Ia) wherein A1b is N, R2 is F, A1 isN, R5is CH2OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.140 provides compounds E140.1 to E140.1135 of formula (Ia) wherein A1b is N, R2 is F, A1 isN, R5is NHCH2CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.141 provides compounds E141.1 to E141.1135 of formula (Ia) wherein A1b is N, R2 is Cl, A1 isCH, R5is CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.142 provides compounds E142.1 to E142.1135 of formula (Ia) wherein A1b is N, R2 is Cl, A1 isCH, R5is OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.143 provides compounds E143.1 to E143.1135 of formula (Ia) wherein A1b is N, R2 is Cl, A1 isCH, R5is cyclopropyl and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.144 provides compounds E144.1 to E144.1135 of formula (Ia) wherein A1b is N, R2 is Cl, A1 isCH, R5is CH2OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.145 provides compounds E145.1 to E145.1135 of formula (Ia) wherein A1b is N, R2 is Cl, A1 isCH, R5is NHCH2CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.146 provides compounds E146.1 to E146.1135 of formula (Ia) wherein A1b is N, R2 is Cl, A1 isN, R5is CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.147 provides compounds E147.1 to E147.1135 of formula (Ia) wherein A1b is N, R2 is Cl, A1 isN, R5is OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.148 provides compounds E148.1 to E148.1135 of formula (Ia) wherein A1b is N, R2 is Cl, A1 isN, R5is cyclopropyl and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.149 provides compounds E149.1 to E149.1135 of formula (Ia) wherein A1b is N, R2 is Cl, A1 isN, R5is CH2OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.150 provides compounds E150.1 to E150.1135 of formula (Ia) wherein A1b is N, R2 is Cl, A1 isN, R5is NHCH2CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.151 provides compounds E151.1 to E151.1135 of formula (Ia) wherein A1b is N, R2 is Br, A1 isCH, R5is CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.152 provides compounds E152.1 to E152.1135 of formula (Ia) wherein A1b is N, R2 is Br, A1 isCH, R5is OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.153 provides compounds E153.1 to E153.1135 of formula (Ia) wherein A1b is N, R2 is Br, A1 isCH, R5is cyclopropyl and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.154 provides compounds E154.1 to E154.1135 of formula (Ia) wherein A1b is N, R2 is Br, A1 isCH, R5is CH2OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.155 provides compounds E155.1 to E155.1135 of formula (Ia) wherein A1b is N, R2 is Br, A1 isCH, R5is NHCH2CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.156 provides compounds E156.1 to E156.1135 of formula (Ia) wherein A1b is N, R2 is Br, A1 isN, R5is CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.157 provides compounds E157.1 to E157.1135 of formula (Ia) wherein A1b is N, R2 is Br, A1 isN, R5is OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.158 provides compounds E158.1 to E158.1135 of formula (Ia) wherein A1b is N, R2 is Br, A1 isN, R5is cyclopropyl and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.159 provides compounds E159.1 to E159.1135 of formula (Ia) wherein A1b is N, R2 is Br, A1 isN, R5is CH2OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.160 provides compounds E160.1 to E160.1135 of formula (Ia) wherein A1b is N, R2 is Br, A1 isN, R5is NHCH2CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.161 provides compounds E161.1 to E161.1135 of formula (Ia) wherein A1b is N, R2 is CN, A1 isCH, R5is CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.162 provides compounds E162.1 to E162.1135 of formula (Ia) wherein A1b is N, R2 is CN, A1 isCH, R5is OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.163 provides compounds E163.1 to E163.1135 of formula (Ia) wherein A1b is N, R2 is CN, A1 isCH, R5is cyclopropyl and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.164 provides compounds E164.1 to E164.1135 of formula (Ia) wherein A1b is N, R2 is CN, A1 isCH, R5is CH2OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.165 provides compounds E165.1 to E165.1135 of formula (Ia) wherein A1b is N, R2 is CN, A1 isCH, R5is NHCH2CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.166 provides compounds E166.1 to E166.1135 of formula (Ia) wherein A1b is N, R2 is CN, A1 isN, R5is CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.167 provides compounds E167.1 to E167.1135 of formula (Ia) wherein A1b is N, R2 is CN, A1 isN, R5is OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.168 provides compounds E168.1 to E168.1135 of formula (Ia) wherein A1b is N, R2 is CN, A1 isN, R5is cyclopropyl and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.169 provides compounds E169.1 to E169.1135 of formula (Ia) wherein A1b is N, R2 is CN, A1 isN, R5is CH2OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.170 provides compounds E170.1 to E170.1135 of formula (Ia) wherein A1b is N, R2 is CN, A1 isN, R5is NHCH2CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.171 provides compounds E171.1 to E171.1135 of formula (Ia) wherein A1b is N, R2 is OCH3, A1is CH, R5is CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.172 provides compounds E172.1 to E172.1135 of formula (Ia) wherein A1b is N, R2 is OCH3, A1is CH, R5is OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.173 provides compounds E173.1 to E173.1135 of formula (Ia) wherein A1b is N, R2 is OCH3, A1is CH, R5is cyclopropyl and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.174 provides compounds E174.1 to E174.1135 of formula (Ia) wherein A1b is N, R2 is OCH3, A1is CH, R5is CH2OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.175 provides compounds E175.1 to E175.1135 of formula (Ia) wherein A1b is N, R2 is OCH3, A1is CH, R5is NHCH2CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.176 provides compounds E176.1 to E176.1135 of formula (Ia) wherein A1b is N, R2 is OCH3, A1is N, R5is CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.177 provides compounds E177.1 to E177.1135 of formula (Ia) wherein A1b is N, R2 is OCH3, A1is N, R5is OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.178 provides compounds E178.1 to E178.1135 of formula (Ia) wherein A1b is N, R2 is OCH3, A1is N, R5is cyclopropyl and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.179 provides compounds E179.1 to E179.1135 of formula (Ia) wherein A1b is N, R2 is OCH3, A1is N, R5is CH2OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.180 provides compounds E180.1 to E180.1135 of formula (Ia) wherein A1b is N, R2 is OCH3, A1is N, R5is NHCH2CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.181 provides compounds E181.1 to E181.1135 of formula (Ia) wherein A1b is N, R2 is OCH2CH3,A1is CH, R5is CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.182 provides compounds E182.1 to E182.1135 of formula (Ia) wherein A1b is N, R2 is OCH2CH3,A1is CH, R5is OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.183 provides compounds E183.1 to E183.1135 of formula (Ia) wherein A1b is N, R2 is OCH2CH3,A1is CH, R5is cyclopropyl and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.184 provides compounds E184.1 to E184.1135 of formula (Ia) wherein A1b is N, R2 is OCH2CH3,A1is CH, R5is CH2OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.185 provides compounds E185.1 to E185.1135 of formula (Ia) wherein A1b is N, R2 is OCH2CH3,A1is CH, R5is NHCH2CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.186 provides compounds E186.1 to E186.1135 of formula (Ia) wherein A1b is N, R2 is OCH2CH3,A1is N, R5is CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.187 provides compounds E187.1 to E187.1135 of formula (Ia) wherein A1b is N, R2 is OCH2CH3,A1is N, R5is OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.188 provides compounds E188.1 to E188.1135 of formula (Ia) wherein A1b is N, R2 is OCH2CH3,A1is N, R5is cyclopropyl and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.189 provides compounds E189.1 to E189.1135 of formula (Ia) wherein A1b is N, R2 is OCH2CH3,A1is N, R5is CH2OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.190 provides compounds E190.1 to E190.1135 of formula (Ia) wherein A1b is N, R2 is OCH2CH3,A1is N, R5is NHCH2CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.191 provides compounds E191.1 to E191.1135 of formula (Ia) wherein A1b is N, R2 is CO2CH3,A1is CH, R5is CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.192 provides compounds E192.1 to E192.1135 of formula (Ia) wherein A1b is N, R2 is CO2CH3,A1is CH, R5is OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.193 provides compounds E193.1 to E193.1135 of formula (Ia) wherein A1b is N, R2 is CO2CH3,A1is CH, R5is cyclopropyl and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.194 provides compounds E194.1 to E194.1135 of formula (Ia) wherein A1b is N, R2 is CO2CH3,A1is CH, R5is CH2OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.195 provides compounds E195.1 to E195.1135 of formula (Ia) wherein A1b is N, R2 is CO2CH3,A1is CH, R5is NHCH2CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.196 provides compounds E196.1 to E196.1135 of formula (Ia) wherein A1b is N, R2 is CO2CH3,A1is N, R5is CH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.197 provides compounds E197.1 to E197.1135 of formula (Ia) wherein A1b is N, R2 is CO2CH3,A1is N, R5is OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.198 provides compounds E198.1 to E198.1135 of formula (Ia) wherein A1b is N, R2 is CO2CH3,A1is N, R5is cyclopropyl and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.199 provides compounds E199.1 to E199.1135 of formula (Ia) wherein A1b is N, R2 is CO2CH3,A1is N, R5is CH2OCH3 and R1, A3, R4, A2a, A2bare as defined in table Z.Table 1.200 provides compounds E200.1 to E200.1135 of formula (Ia) wherein A1b is N, R2 is CO2CH3,A1is N, R5is NHCH2CH3 and R1, A3, R4, A2a, A2bare as defined in table Z. Compounds according to the invention 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, improved physico-chemicalproperties, or increased biodegradability). Compounds according to the invention have particularlyadvantageous levels of biological activity for protecting plants against oomycetes such as Phytophthora,Plasmopara and Pythium.Compounds of formula (I) can be made as shown in the following schemes 1 to 16, in which, unlessotherwise stated, the definition of each variable is as defined in the present invention. Compounds of formula (I) can be prepared via Suzuki cross coupling of compounds of formula (II), wherein X is Cl, Br or I, and a compound of formula (III), wherein either R6is independently from each other hydrogen, C1-6alkyl or wherein two R6together can form a C3-8cycloalkyl, in the presence of a base, such as Cs2CO3, K2CO3 or NaOtBu, and a suitable palladium catalyst, such as tetrakistriphenylphosphinepalladium, [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II), bis(diphenylphosphine)palladium(II) chloride, palladium dichloride or palladium acetate, in a suitable solvent, such as dimethylformamide, dioxane, tetrahydrofuran, ethanol or water. Compounds of formula(III), wherein either R6 is independently from each other hydrogen, C1-6alkyl or wherein two R6 togethercan form a C3-8cycloalkyl are prepared by known methods or are commercially available. Thistransformation is depicted in Scheme 1. Compounds of formula (II) can be prepared by reacting compounds of formula (IV), wherein X is Cl, Bror I, with a reagent of formula (V), wherein X1 is a good leaving group such as Cl, Br, I, triflate, tosyl ormesyl, in the presence of a base such as Cs2CO3, K2CO3, NaH or NaOtBu. A compound of formula (VI), wherein R7is an electron-withdrawing group such as a cyano or an ester, can alternatively be used tofunctionalize the amide nitrogen. Compounds of formula (IV), wherein X is Cl, Br or I, can be preparedby a peptide-coupling reaction from a compound of formula (VII), wherein X is Cl, Br or I, and byactivating the carboxylic acid function of the compounds of formula (VII), a process that usually takes place by converting the -OH of the carboxylic acid into a good leaving group, such as a chloride group, for example by using (COCl)2 or SOCl2, prior to treatment with amines of formula (VIII), preferably in a suitable solvent (e.g., N-methylpyrrolidone, acetonitrile, dimethylacetamide, dichloromethane or tetrahydrofuran), preferably at temperatures between 25 °C and 60 °C, and optionally in the presence of a base such as triethylamine or N,N-diisopropylethylamine; or alternatively under conditions described in the literature for an amide coupling such as 1-propanephosphonic acid cyclic anhydride (T3P) in suitable solvent (e.g., acetonitrile) optionally in the presence of a base (e.g., triethylamine orN,N-diisopropylethylamine). For examples, see Chem. Soc. Rev. 2009, 38, 606 and Chem. Soc. Rev.2011, 40, 5084. Alternatively, compounds of formula (II), wherein X is Cl, Br or I, can be obtained by an amide-coupling transformation between compounds of formula (VII), wherein X is Cl, Br or I, and amines of formula (IX) using the conditions described above. These transformations are depicted in Scheme 2. Compounds of formula (IX) are commercially available or can be obtained by reaction of compounds of formula (VIII) with a compound of formula (V) wherein X1is a good leaving group such as Cl, Br, I, triflate, tosyl or mesyl, in the presence of a base such as Cs2CO3, K2CO3, NaH or NaOtBu. Alternatively, compounds of formula (IX) can also be synthesized by reacting compounds of formula (VIII) with compounds of formula (VI), wherein R7is an electron-withdrawing group such as cyano or ester,optionally in the presence of a base such as triethylamine or 1,8-diazabicyclo[5.4.0]undec-7-ene.Alternatively, compounds of formula (IX) can be obtained from amines of formula (VIII) by a reductiveamination with aldehydes of formula (X), e.g. in the presence of NaBH(OAc)3 or NaBH3CN, in a suitablesolvent, optionally in the presence of a Brønsted or Lewis acid such as acetic acid. Alternatively, another reagent system for the reductive amination uses a combination of titanium isopropoxide and NaBH4. The synthesis of compounds of formula (IX) from amines of formula (VIII) is depicted in Scheme 3. Alternatively, compounds of formula (II), wherein X is Cl, Br or I, can be prepared from the reaction of a compound of formula (XI) and a halogenating agent, such as N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide or bromine in a suitable solvent, such as dichloromethane, chloroform, tetrahydrofuran or acetonitrile. Compounds of formula (XI) can be obtained by an amide-coupling transformation of amines of formula (IX) with compounds of formula (XII), and by activating the carboxylic acid function of the compounds of formula (XII), a process that usually takes place by converting the -OH of the carboxylic acid into a good leaving group, such as a chloride group, forexample by using (COCl)2 or SOCl2, prior to treatment with amines of formula (IX), preferably in asuitable solvent (e.g., N-methylpyrrolidone, acetonitrile, dimethylacetamide, dichloromethane or tetrahydrofuran), preferably at temperatures between 25 °C and 60 °C, and optionally in the presence of a base such as triethylamine or N,N-diisopropylethylamine; or alternatively under conditions described in the literature for an amide coupling such as 1-propanephosphonic acid cyclic anhydride (T3P) in suitable solvent (e.g., acetonitrile) optionally in the presence of a base (e.g., triethylamine or N,N-diisopropylethylamine). Alternatively, compounds of formula (XI) can be obtained by alkylation of compounds of formula (XIII) with compounds of formula (V), wherein X1is a good leaving group such as Cl, Br, I, triflate, tosyl or mesyl, in the presence of a base such as Cs2CO3, K2CO3, NaH or NaOtBu. Alternatively, compounds of formula (XI) can also be synthesized by reacting compounds of formula (XIII) with compounds of formula (VI), wherein R7is an electron-withdrawing group such as cyano or ester, optionally in the presence of a base such as triethylamine or 1,8-diazabicyclo[5.4.0]undec-7-ene. Compounds of formula (XIII) can be prepared by a peptide-coupling transformation from compounds offormula (XII) with amines of formula (VIII) using the conditions described above. These transformationsare depicted in Scheme 4.
[0002] 2 H A N Alternatively, compounds of formula (XI) can be synthesized by reacting compounds of formula (XIV), wherein X is Cl, Br or I, with amines of formula (IX) and carbon monoxide in the presence of a catalyst such as [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II), and, optionally, a base such astriethylamine. This transformation is depicted in Scheme 5. Scheme 5 Compounds of formula (VII), wherein X is Cl, Br or I, can be prepared by hydrolysis of esters of formula (XV), wherein X is Cl, Br or I, and R9is C1-6alkyl, for instance by using a base such as lithium hydroxide or sodium hydroxide. Esters of formula (XV), wherein X is Cl, Br or I, and R9is C1-6alkyl, can be obtained by halogenation of compounds of formula (XVI), wherein R9is C1-6alkyl, by using a halogenating reagent such as N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide or bromine in a suitable solvent,such as dichloromethane, chloroform, tetrahydrofuran or acetonitrile. Compounds of formula (XII) canbe prepared by hydrolysis of esters of formula (XVI), wherein R9is C1-6alkyl, for instance by using abase such as lithium hydroxide or sodium hydroxide. These transformations are depicted in Scheme 6.Compounds of formula (XVI), wherein R9 is C1-6alkyl, are commercially available or can be prepared bycarbonylation of compound of formula (XIV), wherein X is Cl, Br or I, using a catalyst such as dichlorobis(triphenylphosphine)palladium or [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium, in the presence of carbon monoxide, a base such as triethylamine or sodium carbonate and an alcohol. This transformation is depicted in Scheme 7. catalyst Scheme 7Compounds of formula (XIVa), wherein X is Cl, Br or I, can be prepared by treating compounds offormula (XVII) with a reagent such as oxalyl chloride or thionyl chloride. Compounds of formula (XVII)can be synthesized by reacting an amine of formula (XVIII), wherein X is Cl, Br or I, with a reagent offormula (XIX), wherein X is Cl, Br or I, for instance under acidic conditions. Compounds of formula (XIVb), wherein X is Cl, Br or I, can be prepared by condensation of a compound of formula (XX),wherein X is Cl, Br or I, with aminoacetaldehyde dimethyl acetal in the presence of an alkyl chloroformateand trialkylphosphite. Examples of such a transformation are described in Synthesis 2004, 12, 1935–1937. These transformations are depicted in Scheme 8. Alternatively, compounds of formula (XVa), wherein A1b is N, X is Cl, Br or I, and R9 is C1-6alkyl, can beprepared by cyclization of compounds of formula (XXI), wherein each X is independently F, Cl, Br or I,and R9 is C1-6alkyl, using a base such as potassium tert butoxide or cesium carbonate, optionally in thepresence of a catalyst such as copper iodide or tris(dibenzylideneacetone)dipalladium, optionally in thepresence of a ligand such as 1,10-phenanthroline or 2-(di-tert-butylphosphino)biphenyl. Compounds offormula (XXI), wherein each X is independently Cl, Br or I, and R9is C1-6alkyl, can be synthesized by reaction of a compound of formula (XXII), wherein each X is independently Cl, Br or I, and R9is C1- 6alkyl, with phosphorus pentasulfide or Lawesson’s reagent (CAS: 19172-47-5) in a suitable solventsuch as toluene, xylene or dichloromethane. Compounds of formula (XXII) can be prepared by reactionof amines of formula (XXIII), wherein each X is independently Cl, Br or I, with compounds of formula (XXIV), wherein R9is C1-6alkyl, in the presence of a base such as triethylamine or potassium carbonate.Compounds of formula (XXIII), wherein each X is independently Cl, Br or I, and compounds of formula(XXIV), wherein R9 is C1-6alkyl, are commercially available or can be prepared by following methodsknown to those skilled in the art. These transformations are depicted in Scheme 9. Alternatively, compounds of formula (XVb), wherein A1bis CR1, X is Cl, Br or I, and R9is C1-6alkyl, can be prepared by cyclization of compounds of formula (XXV), wherein X are independently Cl, Br or I, with compounds of formula (XXVI), wherein R9is C1-6alkyl, in the presence of a base such as potassiumcarbonate or cesium carbonate. Compounds of formula (XXV), wherein X are independently Cl, Br or I,and compounds of formula (XXVI), wherein R9 is C1-6alkyl, are commercially available or can beprepared by following methods known to those skilled in the art. These transformations are depicted in Scheme 10. O 9 (XXV) (XVb) Scheme 10 Alternatively, compounds of formula (I) can be prepared by an amide-coupling transformation of amines of formula (IX) with compounds of formula (XXVII), and by activating the carboxylic acid function of the compounds of formula (XXVII), a process that usually takes place by converting the -OH of the carboxylic acid into a good leaving group, such as a chloride group, for example by using (COCl)2 or SOCl2, prior to treatment with amines of formula (IX), preferably in a suitable solvent (e.g., N-methylpyrrolidone, acetonitrile, dimethylacetamide, dichloromethane or tetrahydrofuran), preferably at temperatures between 25 °C and 60 °C, and optionally in the presence of a base such as triethylamine or N,N- diisopropylethylamine; or alternatively under conditions described in the literature for an amide coupling such as 1-propanephosphonic acid cyclic anhydride (T3P) in suitable solvent (e.g., acetonitrile) optionally in the presence of a base (e.g., triethylamine or N,N-diisopropylethylamine). Compounds of formula (I) can alternatively be prepared by alkylation of compounds of formula (XXVIII) with compounds of formula (V), wherein X1is a good leaving group such as Cl, Br, I, triflate, tosyl or mesyl, in the presenceof a base such as Cs2CO3, K2CO3, NaH or NaOtBu. Alternatively, compounds of formula (I) can also besynthesized by reacting compounds of formula (XXVIII) with compounds of formula (VI), wherein R7is an electron-withdrawing group such as cyano or ester, optionally in the presence of a base such as triethylamine or 1,8-diazabicyclo[5.4.0]undec-7-ene. Compounds of formula (XXVIII) can be synthesizedby a peptide-coupling transformation from compounds of formula (XXVII) and amines of formula (VIII)using the conditions described above. These transformations are depicted in Scheme 11. (XXVIII)Scheme 11Compounds of formula (XXVII) can be obtained by hydrolysis of the ester moiety of compounds offormula (XXIX), wherein R9is C1-6alkyl. Compounds of formula (XXIX), wherein R9is C1-6alkyl, can result from a Suzuki cross-coupling reaction between compounds of formula (XV), wherein X is Cl, Br or I, and R9is C1-6alkyl, and compounds of formula (III), wherein either R6is independently from each otherhydrogen, C1-6alkyl or wherein two R6 together can form a C3-8cycloalkyl, in the presence of a base, suchas Cs2CO3, K2CO3 or NaOtBu, and a suitable palladium catalyst, such as tetrakistriphenylphosphinepalladium, [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II), bis(diphenylphosphine)palladium(II) chloride, palladium dichloride or palladium acetate, in a suitablesolvent, such as dimethylformamide, dioxane, tetrahydrofuran, ethanol or water. These transformationsare depicted in Scheme 12. Alternatively, compounds of formula (I) can be synthesized by reacting compounds of formula (XXX),wherein X is Cl, Br or I, with amines of formula (IX) and carbon monoxide in the presence of a catalyst such as [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II), and, optionally, a base such astriethylamine. Compounds of formula (XXX), wherein X is Cl, Br or I, can be prepared from compoundsof formula (XXXI), wherein either X is independently from each other Cl, Br or I, through a Suzuki cross- coupling with compounds of formula (III), wherein either R6is independently from each other hydrogen,C1-6alkyl or wherein two R6 together can form a C3-8cycloalkyl, in the presence of a base, such asCs2CO3, K2CO3 or NaOtBu, and a suitable palladium catalyst, such as tetrakistriphenylphosphinepalladium, [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II), bis(diphenylphosphine)palladium(II) chloride, palladium dichloride or palladium acetate, in a suitable solvent, such as dimethylformamide, dioxane, tetrahydrofuran, ethanol or water. These transformations are depicted in Scheme 13. Alternatively, compounds of formula (I) can be prepared by the reaction of a compound of formula(XXXII) with compounds of formula (XXXIII) in a peptide-coupling transformation, using the conditionsdescribed above. Compounds of formula (XXXII) can be prepared via Suzuki cross coupling of a compound of formula (II) and a compound of formula (XXXIV), wherein either R6is independently fromeach other hydrogen, C1-6alkyl or wherein two R6 together can form a C3-8cycloalkyl, in the presence of a base, such as Cs2CO3, K2CO3 or NaOtBu, and a suitable palladium catalyst, such as tetrakistriphenylphosphinepalladium, [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II), bis(diphenylphosphine)palladium(II) chloride, palladium dichloride or palladium acetate, in a suitable solvent, such as dimethylformamide, dioxane, tetrahydrofuran, ethanol or water. Compounds of formula(XXXIV), wherein either R6 is independently from each other hydrogen, C1-6alkyl or wherein two R6together can form a C3-8cycloalkyl are prepared by known methods or are commercially available. Thesetransformations are depicted in Scheme 14. Compounds of formula (Ib), wherein Z is S, can be prepared by the reaction of a compound of formula (I), wherein Z is O, with phosphorus pentasulfide or Lawesson’s reagent (CAS: 19172-47-5) in a suitable solvent such as toluene, xylene or dichloromethane. This transformation is depicted in Scheme 15. Alternatively, compounds of formula (Ib), wherein Z is S, can be prepared by the reaction of a compoundof formula (XXXIIb) with compounds of formula (XXXIII), wherein X2 is OH or Cl, in a peptide-couplingtransformation, using the conditions described above. Compounds of formula (XXXIIb) can be prepared by the reaction of a compound of formula (XXXII), with phosphorus pentasulfide or Lawesson’s reagent (CAS: 19172-47-5) in a suitable solvent such as toluene, xylene or dichloromethane. This transformation is depicted in Scheme 16. 1a 1a A N When the term “compound / compounds according to the invention” is used, then this refers to compounds according to the present invention.Alternatively, the compounds according to the present invention can be obtained by using standardsynthesis techniques known to the person skilled in the art. Non-exhaustive examples include oxidationreactions, reduction reactions, hydrolysis reactions, coupling reactions, aromatic nucleophilic or electrophilic substitution reactions, nucleophilic substitution reactions, nucleophilic addition reactions, olefination reactions, oxime formation, alkylation and halogenation reactions.A compound according to the present invention can be converted in a manner known per se into anothercompound according to the present invention by replacing one or more substituents of the startingcompound according to the present invention in the customary manner by (an)other substituent(s)according to the invention. Depending on the choice of the reaction conditions and starting materials which are suitable in each case, it is possible, for example, in one reaction step only to replace one substituent by another substituent according to the invention, or a plurality of substituents can be replaced by other substituents according to the invention in the same reaction step.Salts of the compounds according to the present invention can be prepared in a manner known per se.Thus, for example, acid addition salts of the compounds according to the present invention are obtainedby treatment with a suitable acid or a suitable ion exchanger reagent and salts with bases are obtained by treatment with a suitable base or with a suitable ion exchanger reagent.Salts of the compounds according to the present invention can be converted in the customary mannerinto the free compounds, acid addition salts, for example, by treatment with a suitable basic compound or with a suitable ion exchanger reagent and salts with bases, for example, by treatment with a suitable acid or with a suitable ion exchanger reagent.Salts of the compounds according to the present invention can be converted in a manner known per seinto other salts of the compounds according to the present invention, acid addition salts, for example, into other acid addition salts, for example by treatment of a salt of inorganic acid such as hydrochloride with a suitable metal salt such as a sodium, barium or silver salt, of an acid, for example with silver acetate, in a suitable solvent in which an inorganic salt which forms, for example silver chloride, is insoluble and thus precipitates from the reaction mixture.Depending on the procedure or the reaction conditions, the compounds according to the presentinvention, which have salt-forming properties can be obtained in free form or in the form of salts.The compounds according to the present invention and, where appropriate, the tautomers thereof, ineach case in free form or in salt form, can be present in the form of one of the stereoisomers which are possible or as a mixture of these, for example in the form of pure stereoisomers, such as antipodes and / or diastereomers, or as stereoisomer mixtures, such as enantiomer mixtures, for example racemates, diastereomer mixtures or racemate mixtures, depending on the number, absolute and relative configuration of asymmetric carbon atoms which occur in the molecule and / or depending on the configuration of non-aromatic double bonds which occur in the molecule; the invention relates to the pure stereoisomers and also to all stereoisomer mixtures which are possible and is to be understood in each case in this sense hereinabove and hereinbelow, even when stereochemical details are not mentioned specifically in each case. Diastereomer mixtures or racemate mixtures of the compounds according to the present invention, in free form or in salt form, which can be obtained depending on which starting materials and procedures have been chosen can be separated in a known manner into the pure diastereomers or racemates on the basis of the physicochemical differences of the components, for example by fractional crystallization, distillation and / or chromatography. Enantiomer mixtures, such as racemates, which can be obtained in a similar manner can be resolved into the optical antipodes by known methods, for example by recrystallization from an optically active solvent, by chromatography on chiral adsorbents, for example high-performance liquid chromatography (HPLC) on acetyl cellulose, with the aid of suitable microorganisms, by cleavage with specific, immobilized enzymes, via the formation of inclusion compounds, for example using chiral crown ethers, where only one enantiomer is complexed, or by conversion into diastereomeric salts, for example by reacting a basic end-product racemate with an optically active acid, such as a carboxylic acid, for example camphor, tartaric or malic acid, or sulfonic acid, for example camphorsulfonic acid, and separating the diastereomer mixture which can be obtained in this manner, for example by fractional crystallization based on their differing solubilities, to give the diastereomers, from which the desired enantiomer can be set free by the action of suitable agents, for example basic agents. Pure diastereomers or enantiomers can be obtained according to the invention not only by separating suitable stereoisomer mixtures, but also by generally known methods of diastereoselective or enantioselective synthesis, for example by carrying out the process according to the invention with starting materials of a suitable stereochemistry.N-oxides can be prepared by reacting a compound according to the present invention with a suitableoxidizing 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., 32 (12), 2561-73, 1989 or WO 00 / 15615. It is advantageous to isolate or synthesize in each case the biologically more effective stereoisomer, for example enantiomer or diastereomer, or stereoisomer mixture, for example enantiomer mixture or diastereomer mixture, if the individual components have a different biological activity.The compounds according to the present invention and, where appropriate, the tautomers thereof, ineach 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. The following Examples illustrate, but do not limit, the invention.The compounds of formula (I) as defined in the present invention can be used in the agricultural sectorand related fields of use e.g. as active ingredients for controlling plant pathogens or on non-living materials for 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 may be used for protecting numerous cultivated plants. The compounds of formula (I) asdefined in the present invention can be used to inhibit or destroy the pathogens that occur on plants orparts of plants (fruit, blossoms, leaves, stems, tubers, roots) of different crops of useful plants, while at the same time protecting also those parts of the plants that grow later e.g. from phytopathogenic microorganisms.It is also possible to use compounds of formula (I) as defined in the present invention as fungicide. Theterm “fungicide” as used herein means a compound that controls, modifies, or prevents the growth of fungi. The term “fungicidally effective amount” 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.It is also possible to use compounds of formula (I) as defined in the present invention as dressing agentsfor the treatment of plant propagation material, e.g., seed, such as fruits, tubers or grains, or plant cuttings (for example rice), for the protection against fungal infections as well as against phytopathogenic fungi occurring in the soil. The propagation material can be treated with a compositioncomprising a compound of formula (I) as defined in the present invention before planting: seed, forexample, can be dressed before being sown. The compounds of formula (I) as defined in the presentinvention can also be applied to grains (coating), either by impregnating the seeds in a liquid formulationor 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.Furthermore the compounds of formula (I) as defined in the present invention can be used for controllingfungi in related areas, for example in the protection of technical materials, including wood and wood related technical products, in food storage, in hygiene management. In addition, the invention could be used to protect non-living materials from fungal attack, e.g. lumber, wall boards and paint.Compounds of formula (I) as defined in the present invention and fungicidal compositions containingthem may be used to control plant diseases caused by a broad spectrum of fungal plant pathogens. They are effective in controlling a broad spectrum of plant diseases, such as foliar pathogens of ornamental, turf, vegetable, field, cereal, and fruit crops. These fungi and fungal vectors of disease, as well as phytopathogenic bacteria and viruses, which may be controlled are for example:Absidia corymbifera, Alternaria spp, Aphanomyces spp, Ascochyta spp, Aspergillus spp. including A.flavus, A. fumigatus, A. nidulans, A. niger, A. terrus, Aureobasidium spp. including A. pullulans,Blastomyces dermatitidis, Blumeria graminis, Bremia lactucae, Botryosphaeria spp. including B. dothidea, B. obtusa, Botrytis spp. inclusing B. cinerea, Candida spp. including C. albicans, C. glabrata,C. krusei, C. lusitaniae, C. parapsilosis, C. tropicalis, Cephaloascus fragrans, Ceratocystis spp,Cercospora spp. including C. arachidicola, Cercosporidium personatum, Cladosporium spp, Claviceps purpurea, Coccidioides immitis, Cochliobolus spp, Colletotrichum spp. including C. musae,Cryptococcus neoformans, Diaporthe spp, Didymella spp, Drechslera spp, Elsinoe spp,Epidermophyton spp, Erwinia amylovora, Erysiphe spp. including E. cichoracearum,Eutypa lata, Fusarium spp. including F. culmorum, F. graminearum, F. langsethiae, F. moniliforme, F.oxysporum, F. proliferatum, F. subglutinans, F. solani, Gaeumannomyces graminis, Gibberella fujikuroi,Gloeodes pomigena, Gloeosporium musarum, Glomerella cingulate, Guignardia bidwellii, Gymnosporangium juniperi-virginianae, Helminthosporium spp, Hemileia spp, Histoplasma spp. including H. capsulatum, Laetisaria fuciformis, Leptographium lindbergi, Leveillula taurica, Lophodermium seditiosum, Microdochium nivale, Microsporum spp, Monilinia spp, Mucor spp, Mycosphaerella spp. including M. graminicola, M. pomi, Oncobasidium theobromaeon, Ophiostoma piceae, Paracoccidioides spp, Penicillium spp. including P. digitatum, P. italicum, Petriellidium spp, Peronosclerospora spp. Including P. maydis, P. philippinensis and P. sorghi, Peronospora spp, Phaeosphaeria nodorum, Phakopsora pachyrhizi, Phellinus igniarus, Phialophora spp, Phoma spp, Phomopsis viticola, Phytophthora spp. including P. infestans, Plasmopara spp. including P. halstedii, P. viticola, Pleospora spp., Podosphaera spp. including P. leucotricha, Polymyxa graminis, Polymyxa betae, Pseudocercosporella herpotrichoides, Pseudomonas spp, Pseudoperonospora spp. including P. cubensis, P. humuli, Pseudopeziza tracheiphila, Puccinia Spp. including P. hordei, P. recondita, P. striiformis, P. triticina, Pyrenopeziza spp, Pyrenophora spp, Pyricularia spp. including P. oryzae, Pythiumspp. including P. ultimum, Ramularia spp, Rhizoctonia spp, 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. tritici, Sphaerotheca macularis, Sphaerotheca fusca (Sphaerotheca fuliginea), Sporothorix spp, Stagonospora nodorum, Stemphylium spp, Stereum hirsutum, Thanatephorus cucumeris, Thielaviopsis basicola, Tilletia spp, Trichoderma spp. including T. harzianum, T. pseudokoningii, T. viride, Trichophyton spp, Typhula spp, Uncinula necator, Urocystis spp, Ustilago spp, Venturia spp. including V. inaequalis, Verticillium spp, and Xanthomonas spp.In particular, compounds of formula (I) as defined in the present invention and fungicidal compositionscontaining them may be used to control plant diseases caused by a broad spectrum of fungal plant pathogens in the Basidiomycete, Ascomycete, Oomycete and / or Deuteromycete, Blasocladiomycete,Chrytidiomycete, Glomeromycete and / or Mucoromycete classes. More particularly, the compounds offormula (I) as defined in the present invention may be used to conrol oomycetes.These pathogens may include:Oomycetes, including Phytophthora diseases such as those caused by Phytophthora capsici,Phytophthora infestans, Phytophthora sojae, Phytophthora fragariae, Phytophthora nicotianae,Phytophthora cinnamomi, Phytophthora citricola, Phytophthora citrophthora and Phytophthoraerythroseptica; Pythium diseases such as those caused by Pythium aphanidermatum, Pythiumarrhenomanes, Pythium graminicola, Pythium irregulare, Pythium sylvaticum and Pythium ultimum;diseases caused by Peronosporales such as Peronospora destructor, Peronospora parasitica,Plasmopara viticola, Plasmopara halstedii, Pseudoperonospora cubensis, Albugo candida,Sclerophthora macrospora and Bremia lactucae; and others such as Aphanomyces cochlioides,Labyrinthula zosterae, Peronosclerospora sorghi and Sclerospora graminicola.Ascomycetes, including blotch, spot, blast or blight diseases and / or rots for example those caused byPleosporales such as Stemphylium solani, Stagonospora tainanensis, Spilocaea oleaginea,Setosphaeria turcica, Pyrenochaeta lycoperisici, Pleospora herbarum, Phoma destructiva,Phaeosphaeria herpotrichoides, Phaeocryptocus gaeumannii, Ophiosphaerella graminicola,Ophiobolus graminis, Leptosphaeria maculans, Hendersonia creberrima, Helminthosporiumtriticirepentis, Setosphaeria turcica, Drechslera glycines, Didymella bryoniae, Cycloconium oleagineum,Corynespora cassiicola, Cochliobolus sativus, Bipolaris cactivora, Venturia inaequalis, Pyrenophorateres, Pyrenophora tritici-repentis, Alternaria alternata, Alternaria brassicicola, Alternaria solani andAlternaria tomatophila, Capnodiales such as Septoria tritici, Septoria nodorum, Septoria glycines,Cercospora arachidicola, Cercospora sojina, Cercospora zeae-maydis, Cercosporella capsellae andCercosporella herpotrichoides, Cladosporium carpophilum, Cladosporium effusum, Passalora fulva,Cladosporium oxysporum, Dothistroma septosporum, Isariopsis clavispora, Mycosphaerella fijiensis,Mycosphaerella graminicola, Mycovellosiella koepkeii, Phaeoisariopsis bataticola, Pseudocercosporavitis, Pseudocercosporella herpotrichoides, Ramularia beticola, Ramularia collo-cygni, Magnaporthalessuch as Gaeumannomyces graminis, Magnaporthe grisea, Pyricularia oryzae, Diaporthales such asAnisogramma anomala, Apiognomonia errabunda, Cytospora platani, Diaporthe phaseolorum, Disculadestructiva, Gnomonia fructicola, Greeneria uvicola, Melanconium juglandinum, Phomopsis viticola,Sirococcus clavigignenti-juglandacearum, Tubakia dryina, Dicarpella spp., Valsa ceratosperma, andothers such as Actinothyrium graminis, Ascochyta pisi, Aspergillus flavus, Aspergillus fumigatus,Aspergillus nidulans, Asperisporium caricae, Blumeriella jaapii, Candida spp., Capnodium ramosum,Cephaloascus spp., Cephalosporium gramineum, Ceratocystis paradoxa, Chaetomium spp.,Hymenoscyphus pseudoalbidus, Coccidioides spp., Cylindrosporium padi, Diplocarpon malae,Drepanopeziza campestris, Elsinoe ampelina, Epicoccum nigrum, Epidermophyton spp., Eutypa lata, Geotrichum candidum, Gibellina cerealis, Gloeocercospora sorghi, Gloeodes pomigena, Gloeosporiumperennans; Gloeotinia temulenta, Griphospaeria corticola, Kabatiella lini, Leptographium microsporum,Leptosphaerulinia crassiasca, Lophodermium seditiosum, Marssonina graminicola, Microdochiumnivale, Monilinia fructicola, Monographella albescens, Monosporascus cannonballus, Naemacyclusspp., Ophiostoma novo-ulmi, Paracoccidioides brasiliensis, Penicillium expansum, Pestalotia rhododendri, Petriellidium spp., Pezicula spp., Phialophora gregata, Phyllachora pomigena, Phymatotrichum omnivora, Physalospora abdita, Plectosporium tabacinum, Polyscytalum pustulans, Pseudopeziza medicaginis, Pyrenopeziza brassicae, Ramulispora sorghi, Rhabdocline pseudotsugae,Rhynchosporium secalis, Sacrocladium oryzae, Scedosporium spp., Schizothyrium pomi, Sclerotiniasclerotiorum, Sclerotinia minor; Sclerotium spp., Typhula ishikariensis, Seimatosporium mariae,Lepteutypa cupressi, Septocyta ruborum, Sphaceloma perseae, Sporonema phacidioides, Stigmina palmivora, Tapesia yallundae, Taphrina bullata, Thielviopsis basicola, Trichoseptoria fructigena, Zygophiala jamaicensis; powdery mildew diseases for example those caused by Erysiphales such as Blumeria graminis, Erysiphe polygoni, Uncinula necator, Sphaerotheca fuligena, Podosphaeraleucotricha, Podospaera macularis Golovinomyces cichoracearum, Leveillula taurica, Microsphaeradiffusa, Oidiopsis gossypii, Phyllactinia guttata and Oidium arachidis; molds for example those causedby Botryosphaeriales such as Dothiorella aromatica, Diplodia seriata, Guignardia bidwellii, Botrytiscinerea, Botryotinia allii, Botryotinia fabae, Fusicoccum amygdali, Lasiodiplodia theobromae, Macrophoma theicola, Macrophomina phaseolina, Phyllosticta cucurbitacearum; anthracnoses for example those caused by Glommerelales such as Colletotrichum gloeosporioides, Colletotrichumlagenarium, Colletotrichum gossypii, Glomerella cingulata, and Colletotrichum graminicola; and wilts orblights for example those caused by Hypocreales such as Acremonium strictum, Claviceps purpurea,Fusarium culmorum, Fusarium graminearum, Fusarium virguliforme, Fusarium oxysporum, Fusariumsubglutinans, Fusarium oxysporum f.sp. cubense, Gerlachia nivale, Gibberella fujikuroi, Gibberellazeae, Gliocladium spp., Myrothecium verrucaria, Nectria ramulariae, Trichoderma viride, Trichothecium roseum, and Verticillium theobromae. Basidiomycetes, including smuts for example those caused by Ustilaginales such as Ustilaginoidea virens, Ustilago nuda, Ustilago tritici, Ustilago zeae, rusts for example those caused by Pucciniales suchas Cerotelium fici, Chrysomyxa arctostaphyli, Coleosporium ipomoeae, Hemileia vastatrix, Pucciniaarachidis, Puccinia cacabata, Puccinia graminis, Puccinia recondita, Puccinia sorghi, Puccinia hordei,Puccinia striiformis f.sp. Hordei, Puccinia striiformis f.sp. Secalis, Pucciniastrum coryli, or Uredinalessuch as Cronartium ribicola, Gymnosporangium juniperi-viginianae, Melampsora medusae, Phakopsora pachyrhizi, Phragmidium mucronatum, Physopella ampelosidis, Tranzschelia discolor and Uromyces viciae-fabae; and other rots and diseases such as those caused by Cryptococcus spp., Exobasidium vexans, Marasmiellus inoderma, Mycena spp., Sphacelotheca reiliana, Typhula ishikariensis, Urocystisagropyri, Itersonilia perplexans, Corticium invisum, Laetisaria fuciformis, Waitea circinata, Rhizoctoniasolani, Thanetephorus cucurmeris, Entyloma dahliae, Entylomella microspora, Neovossia moliniae andTilletia caries. Blastocladiomycetes, such as Physoderma maydis.Mucoromycetes, such as Choanephora cucurbitarum.; Mucor spp.; Rhizopus arrhizus.As well as diseases caused by other species and genera closely related to those listed above. In addition to their fungicidal activity, the compounds and compositions comprising compounds offormula (I) as defined in the present invention may also have activity against bacteria such as Erwiniaamylovora, Erwinia caratovora, Xanthomonas campestris, Pseudomonas syringae, Strptomycesscabies and other related species as well as certain protozoa. Within the scope of the 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. The useful plants and / or target crops in accordance with the invention include conventional as well as genetically enhanced or engineered varieties such as, for example, insect resistant (e.g. Bt. and VIPvarieties) as well as disease resistant, herbicide tolerant (e.g. glyphosate- and glufosinate-resistantmaize varieties commercially available under the trade names RoundupReady® and LibertyLink®) and nematode tolerant varieties. By way of example, suitable genetically enhanced or engineered crop varieties include the Stoneville 5599BR cotton and Stoneville 4892BR cotton varieties. The term "useful plants" and / or “target crops” is to be understood as including also 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 PPO (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 engineeringmethods include glyphosate- and glufosinate-resistant maize varieties commercially available under thetrade names RoundupReady®, Herculex I® and LibertyLink®. The term "useful plants" and / or “target crops” is to be understood as including those which naturally are or have been rendered resistant to harmful insects. This includes plants transformed by the use of recombinant DNA techniques, for example, to be capable of synthesising one or more selectively acting toxins, such as are known, for example, from toxin-producing bacteria. Examples of toxins which can be expressed include ^-endotoxins, vegetative insecticidal proteins (Vip), insecticidal proteins of bacteria colonising nematodes, and toxins produced by scorpions, arachnids, wasps and fungi. Anexample of a crop that has been modified to express the Bacillus thuringiensis toxin is the Bt maizeKnockOut^ (Syngenta Seeds). An example of a crop comprising more than one gene that codes forinsecticidal resistance and thus expresses more than one toxin is VipCot^ (Syngenta Seeds). Crops or seed material thereof can also be resistant to multiple types of pests (so-called stacked transgenic events when created by genetic modification). For example, a plant can have the ability to express aninsecticidal protein while at the same time being herbicide tolerant, for example Herculex I^ (DowAgroSciences, Pioneer Hi-Bred International). The term "useful plants" and / or “target crops” is to be understood as including also useful plants which have been so transformed by the use of recombinant DNA techniques that they are capable of synthesising antipathogenic substances having a selective action, such as, for example, the so-called "pathogenesis-related proteins" (PRPs, see e.g. EP-A-0392225). Examples of such antipathogenic substances and transgenic plants capable of synthesising such antipathogenic substances are known,for example, from EP-A-0392225, WO 95 / 33818, and EP-A-0353191. The methods of producing suchtransgenic plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above. Toxins that can be expressed by transgenic plants include, for example, insecticidal proteins from Bacillus cereus or Bacillus popilliae; or insecticidal proteins from Bacillus thuringiensis, such as ^- endotoxins, e.g. Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), e.g. Vip1, Vip2, Vip3 or Vip3A; or insecticidal proteins of bacteria colonising 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. Further, in the context of the present invention there are to be understood by ^-endotoxins, for example Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, 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, WO 02 / 15701). Truncated toxins, for example a truncated Cry1Ab, 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 WO03 / 018810). More examples of such toxins or transgenic plants capable of synthesising such toxins are disclosed, for example, in EP-A-0374753, WO93 / 07278, WO95 / 34656, EP-A-0427529, EP-A-451878 and WO03 / 052073. The processes for the preparation of such transgenic plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above. CryI-type deoxyribonucleic acids and their preparation are known, for example, from WO 95 / 34656, EP-A-0367 474, EP-A-0401979 and WO 90 / 13651. 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). 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 plantsare: YieldGard^ (maize variety that expresses a Cry1Ab toxin); YieldGard Rootworm^ (maize varietythat expresses a Cry3Bb1 toxin); YieldGard Plus^ (maize variety that expresses a Cry1Ab and aCry3Bb1 toxin); Starlink^ (maize variety that expresses a Cry9C toxin); Herculex I^ (maize variety thatexpresses a Cry1Fa2 toxin and the enzyme phosphinothricine N-acetyltransferase (PAT) to achievetolerance to the herbicide glufosinate ammonium); NuCOTN 33B^ (cotton variety that expresses aCry1Ac toxin); Bollgard I^ (cotton variety that expresses a Cry1Ac toxin); Bollgard II® (cotton varietythat expresses a Cry1Ac and a Cry2Ab toxin); VipCot^ (cotton variety that expresses a Vip3A and aCry1Ab toxin); NewLeaf^ (potato variety that expresses a Cry3A toxin); NatureGard^, Agrisure® GTAdvantage (GA21 glyphosate-tolerant trait), Agrisure® CB Advantage (Bt11 corn borer (CB) trait) and Protecta^. Further examples of such transgenic crops are:1. Bt11 Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France,registration number C / FR / 96 / 05 / 10. Genetically modified Zea mays which has been rendered resistantto attack by the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) by transgenicexpression of a truncated Cry1Ab toxin. Bt11 maize also transgenically expresses the enzyme PAT to achieve tolerance to the herbicide glufosinate ammonium.2. Bt176 Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France,registration number C / FR / 96 / 05 / 10. Genetically modified Zea mays which has been rendered resistantto attack by the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) by transgenicexpression of a Cry1Ab toxin. Bt176 maize also transgenically expresses the enzyme PAT to achieve tolerance to the herbicide glufosinate ammonium.3. MIR604 Maize from Syngenta Seeds SAS, Chemin de l'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 WO 03 / 018810.4. MON 863 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150 Brussels,Belgium, registration number C / DE / 02 / 9. MON 863 expresses a Cry3Bb1 toxin and has resistance to certain Coleoptera insects.5. IPC 531 Cotton from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150 Brussels,Belgium, registration number C / ES / 96 / 02.6. 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 Cry1F for achieving resistance to certain Lepidoptera insects and of the PAT protein for achieving tolerance to the herbicide glufosinate ammonium.7. NK603 × MON 810 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150Brussels, 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 × 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 Cry1Ab toxin obtainedfrom Bacillus thuringiensis subsp. kurstaki which brings about tolerance to certain Lepidoptera, includethe European corn borer. 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. The term “plants” refers to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, stalks, foliage, and fruits. 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 may 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 youngplants may be protected before transplantation by a total or partial treatment by immersion. Preferably“plant propagation material” is understood to denote seeds. Pesticidal agents referred to herein using their common name are known, for example, from "The Pesticide Manual", 19th Ed., British Crop Protection Council 2021.The compounds of formula (I) as defined in the present 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.Suitable carriers and / or adjuvants, e.g. for agricultural use, can be solid or liquid and are substancesuseful 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 WO 97 / 33890. 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. 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. Wettablepowders 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. 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 sulphate, sodium silicate, sodium borate, magnesia, mica, iron oxide, zinc oxide, titanium oxide, antimony oxide, cryolite, gypsum, diatomaceous earth, calcium sulphate 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. 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. 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. 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. Pressurised sprayers, wherein the active ingredient is dispersed in finely-divided form as a result of vaporisation of a low boiling dispersant solvent carrier, may also be used.Suitable agricultural adjuvants and / or carriers that are useful in formulating the compositions of theinvention in the formulation types described above are well known to those skilled in the art. 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, gamma-butyrolactone, 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. 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. 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 sulphate; alkylarylsulfonate salts, such as calcium dodecylbenzenesulfonate; alkylphenol-alkylene oxide addition products, such as nonylphenol-C.sub.18ethoxylate; 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 glycolstearate; block copolymers of ethylene oxide and propylene oxide; and salts of mono and dialkylphosphate esters. 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 biocidally 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 biocidally active ingredients may be fungicides, herbicides, insecticides,bactericides, acaricides, nematicides, plant growth regulators, and / or biologicals.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, UnitedStates Patent No. US 6,919,298 and include, for example, salicylates and the commercial SAR induceracibenzolar-S-methyl.The compounds of formula (I) as defined in the present invention are normally used in the form ofcompositions 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.The compounds of formula (I) as defined in the present invention may be used in the form of (fungicidal)compositions for controlling or protecting against phytopathogenic microorganisms, comprising as activeingredient at least one compound of formula (I) as defined in the present invention or of at least onepreferred individual compound as above-defined, in free form or in agrochemically usable salt form, and at least one of the above-mentioned adjuvants. The invention therefore provides a composition, preferably a fungicidal composition, comprising at leastone compound of formula (I) as defined in the present invention, an agriculturally acceptable carrier andoptionally 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 maycomprise at least one or more pesticidally active compounds, for example an additional fungicidal activeingredient in addition to the compound of formula (I) as defined in the present invention. 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 ofa compound of formula (I) as defined in the present invention or of a preferred individual compound asabove-defined 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. 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. A preferred method of controlling or preventing an infestation of crop plants by phytopathogenic microorganisms, especially fungal organisms, which comprises the application of a compound of formula (I) as defined in the present invention, or an agrochemical composition which contains at least one of said compounds, 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) as defined in the present invention can also penetrate the plant through the roots via the soil (systemicaction) 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) as defined in the present invention 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. A formulation, e.g. a composition containing the compound of formula (I) as defined in the present invention, and, if desired, a solid or liquid adjuvant or monomers for encapsulating the compound of formula (I) as defined in the present invention, 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). The application methods for the compositions, that is the methods of controlling pathogens of the abovementioned type, such as spraying, atomizing, dusting, brushing on, dressing, scattering or pouring- which are to be selected to suit the intended aims of the prevailing circumstances - and the use of thecompositions for controlling pathogens of the abovementioned type are other subjects of the invention. Typical rates of concentration are between 0.1 and 1000 ppm, preferably between 0.1 and 500 ppm, of active ingredient. The rate of application per hectare is preferably 1g to 2000 g of active ingredient per hectare, more preferably 10 to 1000 g / ha, most preferably 10 to 600 g / ha. When used as seed drenching agent, convenient dosages are from 10mg to 1g of active substance per kg of seeds. 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. Suitably, a composition comprising a compound of formula (I) as defined in the present inventionaccording to the present invention is applied either preventative, meaning prior to disease developmentor curative, meaning after disease development. 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 (EO), 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) or any technically feasible formulation in combination with agriculturally acceptable adjuvants. 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, EO 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 sulphonate, an alkylarylsulphonate, a lignin sulphonate, a fatty alkyl sulphate, and ethoxylated alkylphenol and an ethoxylated fatty alcohol. 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. 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) as defined in the present invention together with component (B) and (C), and optionally other active agents, particularly microbiocides or conservatives or the like. Concentrated forms of compositions generally contain in between about 2 and 80%, preferably between about 5 and 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. Whereas it is preferred to formulate commercial products as concentrates, the end user will normally use dilute formulations. EXAMPLES The Examples which follow serve to illustrate the invention. Certain compounds of the invention can be distinguished from known compounds by virtue of greater efficacy at low application rates, which can be verified by the person skilled in the art using the experimental procedures outlined in the Examples. Formulation Examples Wettable powders a) b) c)active ingredient [compound of formula (I)] 25 % 50 % 75 %sodium lignosulfonate 5 % 5 % -sodium lauryl sulfate 3 % - 5 %sodium diisobutylnaphthalenesulfonate - 6 % 10 %phenol polyethylene glycol ether - 2 % -(7-8 mol of ethylene oxide) highly dispersed silicic acid 5 % 10 % 10 % Kaolin 62 % 27 % - The active ingredient 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. Powders for dry seed treatment a) b) c)active ingredient [compound of formula (I)] 25 % 50 % 75 %light mineral oil 5 % 5 % 5 %highly dispersed silicic acid 5 % 5 % -Kaolin 65 % 40 % -Talcum - 20%The active ingredient 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. Emulsifiable concentrate active ingredient [compound of formula (I)] 10 %octylphenol polyethylene glycol ether 3 %(4-5 mol of ethylene oxide) calcium dodecylbenzenesulfonate 3 %castor oil polyglycol ether (35 mol of ethylene oxide) 4 %Cyclohexanone 30 %xylene mixture 50 % Emulsions of any required dilution, which can be used in plant protection, can be obtained from this concentrate by dilution with water. Dusts a) b) c)Active ingredient [compound of formula (I)] 5 % 6 % 4 %talcum 95 % - -Kaolin - 94 % -mineral filler - - 96 %Ready-for-use dusts are obtained by mixing the active ingredient with the carrier and grinding the mixture in a suitable mill. Such powders can also be used for dry dressings for seed. Extruder granules Active ingredient [compound of formula (I)] 15 %sodium lignosulfonate 2 %carboxymethylcellulose 1 %Kaolin 82 % The active ingredient 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. Coated granules Active ingredient [compound of formula (I)] 8 %polyethylene glycol (mol. wt.200) 3 % Kaolin 89 % The finely ground active ingredient is uniformly applied, in a mixer, to the kaolin moistened with polyethylene glycol. Non-dusty coated granules are obtained in this manner. Suspension concentrate active ingredient [compound of formula (I)] 40 %propylene glycol 10 %nonylphenol polyethylene glycol ether (15 mol of ethylene oxide) 6 %Sodium lignosulfonate 10 %carboxymethylcellulose 1 %silicone oil (in the form of a 75 % emulsion in water) 1 %Water 32 %The finely ground active ingredient 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. Flowable concentrate for seed treatment active ingredient [compound of formula (I)] 40 %propylene glycol 5 %copolymer butanol PO / EO 2 %tristyrenephenole with 10-20 moles EO 2 %1,2-benzisothiazolin-3-one (in the form of a 20% solution in water) 0.5 %monoazo-pigment calcium salt 5 %Silicone oil (in the form of a 75 % emulsion in water) 0.2 %Water 45.3 %The finely ground active ingredient 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. Slow Release Capsule Suspension 28 parts of a combination of the compound of formula (I) 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. Analytical Methods: Throughout this description, temperatures are given in degrees Celsius (°C) and “mp.” means melting point. LC-MS means Liquid Chromatography Mass Spectrometry and the description of the apparatus and the method is as follows: Method A:Spectra were recorded on a Shimadzu LCMS 2020 Mass Spectrometer; Column: HALO C182.7 µm,3.0 mm × 30 mm; Mobile Phase: MeCN (with either 0.05% HCOOH or 0.05% TFA) - Water (with either0.05% HCOOH or 0.05% TFA); Gradient: MeCN from 5% to 95% over 1.4 min, hold 0.6 min, total run time is 2.5 min; Flow rate: 1.8 mL / min; Column temperature: 50°C; Wavelength: 214 and 254 nm PDA. Method B: Spectra were recorded on a Mass Spectrometer from Waters (Acquity QDa Mass Spectrometer) equipped with an electrospray source (Polarity: Positive and Negative Polarity Switch), Capillary: 0.8 kV, Cone range: 25 V, Extractor: V (No extractor voltage for QDa detector) Source Temperature: 120°C, Desolvation Temperature: 600°C, Cone Gas Flow: 50 L / h, Desolvation Gas Flow: 1000 L / h, Mass range: 110 to 850 Da) and an Acquity UPLC from Waters: Quaternary solvent manager, heated column compartment , diode-array detector. Column: Acquity UPLC HSS T3 C18, 1.8 µm, 30 x 2.1 mm, Temp: 40 °C, DAD Wavelength range (nm): 200 to 400, Solvent Gradient: A = water + 5% Acetonitrile + 0.1 % HCOOH, B= Acetonitrile + 0.05 % HCOOH: gradient: 0 min 10% B; 0.-0.2 min 10-50% B; 0.2-0.6 min50-100% B; 0.6-1.3 min 100% B; 1.3-1.4 min 100-10% B; 1.4-1.6 min 10% B; Flow (mL / min) 0.6.Method C: 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 µm, 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. Method D: Spectra were recorded on a Mass Spectrometer from Agilent (Single quad mass spectrometer)equipped with a Multimode- Electron Spray and APCI (Polarity: positive and negative ions), Capillary:4.00 kV, Corona Current 4.0 µA, Charging Voltage, 2.00 kV, Nitrogen Gas Flow:12.0 L / min, NebulizerPressure: 40 psig, Mass range: 100 to 1000 m / z), dry gas temperature 250 °C, Vaporizer temperature200 °C and an UPLC from Agilent: quaternary pump, heated column compartment, Variable wave lengthdetector. Column: Eclipse Plus C18, 3.5 µm, 100 x 4.6 mm, column Temp: Ambient, Wavelength (nm):220 nm, Gradient: A = 0.05% TFA in water, B = 0.05% TFA in Acetonitrile. Gradient: time / %B: 0 / 5, 2 / 5,7 / 70, 10 / 95, 12 / 95, 12.1 / 5, 15 / 5; Flow rate: 1.0 mL / min. Method E: Spectra were recorded on a ACQUITY Mass Spectrometer from Waters Corporations (SQD or SQDIISingle quadrupole mass spectrometer) equipped with an electrospray source (Polarity: positive or negativeions, Capillary: 3.0 kV, Cone: 30V, Extractor: 3.00 V, Source Temperature: 150°C, DesolvationTemperature: 400°C, Cone Gas Flow: 60 L / hr, Desolvation Gas Flow: 700 L / hr, Mass range: 140 to 800 Da) and an ACQUITY UPLC from Waters Corporations with solvent degasser, binary pump, heated column compartment and diode-array detector. Column: Waters UPLC HSS T3, 1.8 µm, 30 x 2.1 mm, Temp: 60 °C, DAD Wavelength range (nm): 210 to 400, Solvent Gradient: A = Water / Methanol 9:1 + 0.1% formic acid, B= Acetonitrile + 0.1% formic acid, gradient: 0-100% B in 3.0 min; Flow (ml / min) 0.75. The below Table A gathers for compounds of formula (I):- LC-MS data, such as retention time (RT), [M+H]+,- the type of method, and / or- melting point (mp).Table A: Compound name Structure RT[M+H]+Metho mp (min (measure d (°C ) d) )1 methyl N-[5-[2-[(4-fluoro-3- 1.05 468 B 188 -methoxy-phenyl)-methyl- 190 carbamoyl]thiazolo[5,4- c]pyridin-7-yl]-2- pyridyl]carbamateCompound name Structure RT[M+H]+Metho mp (min (measure d (°C ) d) )methyl N-[4-[2-[(4-fluoro-3- 1.07 466 B 210 -methoxy-phenyl)-methyl- 212 carbamoyl]thieno[2,3- c]pyridin-4- yl]phenyl]carbamatemethyl N-[5-[2-[(4-cyano-3- 1.10 474 A 238 -methoxy-phenyl)-methyl- 239 carbamoyl]thieno[2,3- c]pyridin-4-yl]-2- pyridyl]carbamate4-(6-acetamido-3-pyridyl)- 1.06 451 A 236 -N-(4-fluoro-3-methoxy- 239 phenyl)-N-methyl- thieno[2,3-c]pyridine-2- carboxamidemethyl N-[5-[2- 0.84 506 C[cyanomethyl-(4-fluoro-3- methoxy- phenyl)carbamoyl]-7- methyl-thieno[2,3-c]pyridin- 4-yl]-2-pyridyl]carbamatemethyl N-[5-[2-[(4-fluoro-3- 0.82 481 Cmethoxy-phenyl)-methyl- carbamoyl]-7-methyl- thieno[2,3-c]pyridin-4-yl]-2- pyridyl]carbamatemethyl N-[5-[7-chloro-2- 1.03 526 C[cyanomethyl-(4-fluoro-3- methoxy- phenyl)carbamoyl]thieno[2, 3-c]pyridin-4-yl]-2- pyridyl]carbamateCompound name Structure RT[M+H]+Metho mp (min (measure d (°C ) d) )methyl N-[5-[7-chloro-2-[(4- 1.05 501 Cfluoro-3-methoxy-phenyl)- methyl- carbamoyl]thieno[2,3- c]pyridin-4-yl]-2- pyridyl]carbamatemethyl N-[5-[2-[(4- 0.83 451 Cfluorophenyl)-methyl- carbamoyl]-7-methyl- thieno[2,3-c]pyridin-4-yl]-2- pyridyl]carbamatemethyl N-[5-[7-chloro-2-[(4- 1.04 471 Cfluorophenyl)-methyl- carbamoyl]thieno[2,3- c]pyridin-4-yl]-2- pyridyl]carbamatemethyl N-[5-[2- 0.87 492 C[cyanomethyl-(4-fluoro-3- methoxy- phenyl)carbamoyl]thieno[2, 3-c]pyridin-4-yl]-2- pyridyl]carbamatemethyl N-[5-[2-[(4-fluoro-3- 0.85 481 C 195 -methoxy-phenyl)-methyl- 197 carbamoyl]-3-methyl- thieno[2,3-c]pyridin-4-yl]-2- pyridyl]carbamatemethyl N-[5-[2-[(4- 0.85 451 C 203 -fluorophenyl)-methyl- 205 carbamoyl]-3-methyl- thieno[2,3-c]pyridin-4-yl]-2- pyridyl]carbamateCompound name Structure RT[M+H]+Metho mp (min (measure d (°C ) d) )methyl N-[5-[2-[(4-fluoro-3- 0.86 467 C 218 -methoxy-phenyl)-methyl- 220 carbamoyl]thieno[2,3- c]pyridin-4-yl]-2- pyridyl]carbamatemethyl N-[5-[2-[(4- 0.85 437 C 239 -fluorophenyl)-methyl- 241 carbamoyl]thieno[2,3- c]pyridin-4-yl]-2- pyridyl]carbamate7-(4-acetamidophenyl)-N- 6.26 395 D 220 -(4-chlorophenyl)-N-methyl- 223 thiazolo[5,4-c]pyridine-2- carboxamidemethyl N-[4-[2-[(4- 6.25 437 D 216 -chlorophenyl)-methyl- 219 carbamoyl]thiazolo[5,4- c]pyridin-7- yl]phenyl]carbamatemethyl N-[5-[2-[(4-cyano-3- 0.88 475 Cmethoxy-phenyl)-methyl- carbamoyl]thiazolo[5,4- c]pyridin-7-yl]-2- pyridyl]carbamate4-[6- 1.22 463 E(ethylcarbamoylamino)-3- pyridyl]-N-(6-methoxy-2- pyridyl)-N-methyl- thieno[2,3-c]pyridine-2- carboxamideN-(4-cyano-3-fluoro- 1.17 475 Ephenyl)-4-[6- (ethylcarbamoylamino)-3- pyridyl]-N-methyl-Compound name Structure RT[M+H]+Metho mp (min (measure d (°C ) d) ) thieno[2,3-c]pyridine-2- carboxamideN-(4-cyano-3-methoxy- 1.14 487 Ephenyl)-4-[6- (ethylcarbamoylamino)-3- pyridyl]-N-methyl- thieno[2,3-c]pyridine-2- carboxamide4-[6- 1.14 463 E(ethylcarbamoylamino)-3- pyridyl]-N-(2-methoxy-4- pyridyl)-N-methyl- thieno[2,3-c]pyridine-2- carboxamide4-[6- 1.01 463 E(ethylcarbamoylamino)-3- pyridyl]-N-(4-methoxy-2- pyridyl)-N-methyl- thieno[2,3-c]pyridine-2- carboxamideN-(4-chloro-3-fluoro- 1.32 484 Ephenyl)-4-[6- (ethylcarbamoylamino)-3- pyridyl]-N-methyl- thieno[2,3-c]pyridine-2- carboxamide4-[4-[(2- 1.16 463 Emethoxyacetyl)amino]phen yl]-N-(6-methoxy-2-pyridyl)- N-methyl-thieno[2,3- c]pyridine-2-carboxamideCompound name Structure RT[M+H]+Metho mp (min (measure d (°C ) d) )N-(4-cyano-3-fluoro- 1.16 475 Ephenyl)-4-[4-[(2- methoxyacetyl)amino]phen yl]-N-methyl-thieno[2,3- c]pyridine-2-carboxamideN-(4-cyano-3-methoxy- 1.12 487 Ephenyl)-4-[4-[(2- methoxyacetyl)amino]phen yl]-N-methyl-thieno[2,3- c]pyridine-2-carboxamide4-[4-[(2- 1.1 463 Emethoxyacetyl)amino]phen yl]-N-(2-methoxy-4-pyridyl)- N-methyl-thieno[2,3- c]pyridine-2-carboxamide4-[4-[(2- 0.98 463 Emethoxyacetyl)amino]phen yl]-N-(4-methoxy-2-pyridyl)- N-methyl-thieno[2,3- c]pyridine-2-carboxamideN-(4-chloro-3-fluoro- 1.31 484 Ephenyl)-4-[4-[(2- methoxyacetyl)amino]phen yl]-N-methyl-thieno[2,3- c]pyridine-2-carboxamide4-(4-acetamidophenyl)-N- 1.06 433 E(6-methoxy-2-pyridyl)-N- methyl-thieno[2,3- c]pyridine-2-carboxamide4-(4-acetamidophenyl)-N- 1.07 445 E(4-cyano-3-fluoro-phenyl)- N-methyl-thieno[2,3- c]pyridine-2-carboxamideCompound name Structure RT[M+H]+Metho mp (min (measure d (°C ) d) )4-(4-acetamidophenyl)-N- 1.04 457 E(4-cyano-3-methoxy- phenyl)-N-methyl- thieno[2,3-c]pyridine-2- carboxamide4-(4-acetamidophenyl)-N- 1.01 433 E(2-methoxy-4-pyridyl)-N- methyl-thieno[2,3- c]pyridine-2-carboxamide4-(6-acetamido-3-pyridyl)- 1.06 434 EN-(6-methoxy-2-pyridyl)-N- methyl-thieno[2,3- c]pyridine-2-carboxamide4-(6-acetamido-3-pyridyl)- 1.06 446 EN-(4-cyano-3-fluoro- phenyl)-N-methyl- thieno[2,3-c]pyridine-2- carboxamide4-(6-acetamido-3-pyridyl)- 1.01 434 EN-(2-methoxy-4-pyridyl)-N- methyl-thieno[2,3- c]pyridine-2-carboxamidemethyl N-[5-[2-[(6- 1.19 450 Emethoxy-2-pyridyl)-methyl- carbamoyl]thieno[2,3- c]pyridin-4-yl]-2- pyridyl]carbamatemethyl N-[5-[2-[(4-cyano-3- 1.17 462 Efluoro-phenyl)-methyl- carbamoyl]thieno[2,3- c]pyridin-4-yl]-2- pyridyl]carbamateCompound name Structure RT[M+H]+Metho mp (min (measure d (°C ) d) )40 methyl N-[5-[2-[(2- 1.13 450 Emethoxy-4-pyridyl)-methyl- carbamoyl]thieno[2,3- c]pyridin-4-yl]-2- pyridyl]carbamate41 methyl N-[5-[2-[(4- 1.01 450 Emethoxy-2-pyridyl)-methyl- carbamoyl]thieno[2,3- c]pyridin-4-yl]-2- pyridyl]carbamate Example 1: Preparation of methyl N-[5-[2-[(4-fluoro-3-methoxy-phenyl)-methyl- carbamoyl]thiazolo[5,4-c]pyridin-7-yl]-2-pyridyl]carbamate (Compound 1) OSN a g, in dichloromethane (100.0 mL) was added N,N-diethylethanamine (4.42 g, 43.7 mmol, 1.10 equiv.). Then ethyl 2-chloro-2-oxo- acetate (5.42 g, 39.7 mmol, 1.00 equiv.) was added dropwise at room temperature. The mixture wasstirred at room temperature for 16 hours. Then the resulting mixture was diluted with water and extractedwith dichloromethane. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting with petroleum ether / ethyl acetate) to give ethyl 2-[(3,5-dibromo-4- pyridyl)amino]-2-oxo-acetate. LC-MS (method A): Rt 1.00 min, m / z = 352 [M+H]+Step B: Preparation of ethyl 2-[(3,5-dibromo-4-pyridyl)amino]-2-thioxo-acetate a 4-pyridyl)amino]-2-oxo-acetate (4.00 g, 11.4 mmol, 1.00 equiv.) in toluene (40.0 mL) was added Lawesson reagent (CAS 19172-47-5) (2.30 g, 5.68 mmol, 0.50 equiv.).The mixture was stirred at 70 °C for 16 hours. Then the resulting mixture was diluted with water andextracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting with petroleum ether / ethyl acetate) to give ethyl 2-[(3,5-dibromo-4- pyridyl)amino]-2-thioxo-acetate. LC-MS (method A): Rt 1.19 min, m / z = 368 [M+H]+Step C: Preparation of 7-bromothiazolo[5,4-c]pyridine-2-carboxylic acid a (3,5-dibromo-4-pyridyl)amino]-2-thioxo-acetate (3.00 g, 8.15 mmol, 1.00 equiv.) in 1,2-dimethoxyethane (30.00 mL) was added copper iodide (0.155 g, 0.815 mmol, 0.100 equiv.), 1,10- phenanthroline (0.294 g, 1.63 mmol 0.20 equiv.) and cesium carbonate (3.98 g, 12.2 mmol, 1.50 equiv.). The mixture was heated at 90 °C in a seal tube for 16 hours, then concentrated under reduced pressure. The residue was purified by reverse phase chromatography (eluting acetonitrile / H2O containing 0.1% formic acid) to provide 7-bromothiazolo[5,4-c]pyridine-2-carboxylic acid. LC-MS (method A): Rt 0.98 min, m / z = 258 [M+H]+Step D: Preparation of 7-bromo-N-(4-fluoro-3-methoxy-phenyl)-N-methyl-thiazolo[5,4-c]pyridine-2- carboxamide To a solution of 4-fluoro-3-methoxy-N-methyl-aniline (0.200 g, 1.29 mmol, 1.00 equiv.) and 7- bromothiazolo[5,4-c]pyridine-2-carboxylic acid (0.668 g, 2.58 mmol, 2.00 equiv.) in pyridine (2.0 mL) was added 1-propanephosphonic anhydride (50% in ethyl acetate) (2.46 g, 3.87 mmol, 3.00 equiv) dropwise at 70 °C. The mixture was stirred at 70 °C for 2 hours. The mixture was diluted with water and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure. The crude residue was purified by silica gel column chromatography (eluting with dichloromethane / methanol) to give 7-bromo-N-(4-fluoro-3-methoxy-phenyl)-N-methyl-thiazolo[5,4-c]pyridine-2-carboxamide. LC-MS (method A): Rt 1.30 min, m / z = 396 [M+H]+Step E: Preparation of methyl N-[4-[2-[(4-fluoro-3-methoxy-phenyl)-methyl-carbamoyl]thieno[2,3- c]pyridin-4-yl]phenyl]carbamate (Compound 1) 7-bromo-N-(4-fluoro-3-methoxy-phenyl)-N-methyl-thiazolo[5,4-c]pyridine-2-carboxamide (0.0500 g,0.126 mmol, 1.00 equiv.) and methyl N-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridyl]carbamate (0.0554 g, 0.189 mmol, 1.50 equiv.) were dissolved in acetonitrile (1.0 mL). Then asolution of sodium carbonate (0.0401 g, 0.378 mmol, 3.0 equiv.) in water was added. The resultingreaction mixture was degassed with nitrogen for 15 min. Then XPhos Pd G2 (CAS 1310584-14-5)(0.0102 g, 0.0126 mmol, 0.1 equiv.) was added. The reaction mixture was heated under microwaveirradiation at 100 °C for 1 hour. Then the reaction mixture was cooled down to room temperature, filtered through celite, washingwith methanol. The organic layer was dried under sodium sulphate, filtered, and concentrated under reduced pressure. The crude residue was purified over a silica gel cartridge (cyclohexane / ethyl acetate) to afford methyl N-[5-[2-[(4-fluoro-3-methoxy-phenyl)-methyl- carbamoyl]thiazolo[5,4-c]pyridin-7-yl]-2-pyridyl]carbamate as an off-white solid. (Compound 1) LC-MS (method B): Rt 0.87 min, m / z = 450 [M+H]+1H-NMR (400 MHz, DMSO-d6, ppm) δ = 3.46 (s, 3 H), 3.75(s, 6 H), 6.87 (br d, J = 7.00 Hz, 1 H), 7.11(br t, J = 10.19 Hz, 1 H), 7.36 (br d, J = 5.88 Hz, 1 H), 7.57 (br d, J = 8.63 Hz, 1 H), 7.89 (br d, J = 8.50 Hz, 1 H), 8.49 (br s, 1 H), 8.82 (s, 1 H), 9.42 (s,1 H), 10.35 (br s, 1 H) Example 2: Preparation of methyl N-[4-[2-[(4-fluoro-3-methoxy-phenyl)-methyl- carbamoyl]thieno[2,3-c]pyridin-4-yl]phenyl]carbamate (Compound 2) (Compound 2) Step A: Preparation of methyl 4-bromothieno[2,3-c]pyridine-2-carboxylate (Compound X-1) a 4-carbaldehyde (10.0 g, 37.7 mmol, 1.00 equiv.) in tetrahydrofuran (60.0 mL) was added methyl 2-sulfanylacetate (4.41 g, 41.5 mmol, 1.10 equiv.) at 0 °C. The mixturewas stirred at 0 °C for 1 hour. Then the solution was warmed to room temperature and stirred for 1hour. Then cesium carbonate (12.3 g, 37.7 mmol, 1.00 equiv.) was added at room temperature and the mixture was stirred at room temperature for 16 hours. The mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting with petroleum ether / ethyl acetate) to give methyl 4-bromothieno[2,3-c]pyridine-2-carboxylate. LC-MS (method A): Rt 1.37 min, m / z = 273 [M+H]+1H-NMR (400 MHz, DMSO-d6, ppm) δ = 9.36 (s, 1 H), 8.71 (s, 1 H), 7.99 (s, 1 H), 3.96 (s, 3 H).Step B: Preparation of 4-bromothieno[2,3-c]pyridine-2-carboxylic acid (Compound X-2) (Compound X-2) To a solution of methyl 4-bromothieno[2,3-c]pyridine-2-carboxylate (Compound X-1) (6.10 g, 22.4 mmol,1.00 equiv.) in tetrahydrofuran / water (1:1, 80.0 mL) was added lithium hydroxide (0.805 g, 33.6 mmol,1.50 equiv.). The mixture was stirred at room temperature for 1 hour. Then the organic solvent was removed under reduced pressure. The aqueous solution was adjusted to pH 2-3 with 2N HCl. The precipitate was collected by filtration, washed with water to provide 4-bromothieno[2,3-c]pyridine-2- carboxylic acid (Compound X-2). LC-MS (method A): Rt 1.14 min, m / z = 260 (M+2 H)2+1H-NMR (400 MHz, DMSO-d6, ppm) δ = 9.35 (s, 1H), 8.71 (s, 1H), 7.97 (s, 1H).Step C: Preparation of 4-bromo-N-(4-fluoro-3-methoxy-phenyl)-N-methyl-thieno[2,3-c]pyridine-2- carboxamide (Compound X-3) a[2,3-c]pyridine-2-carboxylic acid (Compound X-2) (1.50 g, 5.81 mmol,1.00 equiv.) in pyridine (20.0 mL) was added 4-fluoro-3-methoxy-N-methyl-aniline (0.992 g, 6.39 mmol, 1.10 equiv.) and 1-propanephosphonic anhydride (50% in ethyl acetate) (11.1 g, 17.4 mmol, 3.00 equiv) dropwise at 65 °C under N2. The mixture was heated at 65 ° C for 2 hours. The final mixture was diluted with saturated aqueous NaHCO3 solution and extracted with ethyl acetate. The combined organic layers were washed with water, dried with sodium sulfate, filtered and concentrated under vacuum. The residue was purified by silica gel column chromatography (eluting with dichloromethane / methanol) to give 4- bromo-N-(4-fluoro-3-methoxy-phenyl)-N-methyl-thieno[2,3-c]pyridine-2-carboxamide. LC-MS (method A): Rt 1.35 min, m / z = 395 [M+H]+Step D: Preparation of methyl N-[4-[2-[(4-fluoro-3-methoxy-phenyl)-methyl-carbamoyl]thieno[2,3- c]pyridin-4-yl]phenyl]carbamate (Compound 2) 4-bromo-N-(4-fluoro-3-methoxy-phenyl)-N-methyl-thieno[2,3-c]pyridine-2-carboxamide (Compound X-3) (0.0500 g, 0.126 mmol), methyl N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate(0.0405 g, 0.139 mmol, 1.10 equiv.) and cesium carbonate (0.123 g, 0.379 mmol, 3.00 equiv.) weresuccessively dissolved in 2-methyltetrahydrofuran (1.01 mL) and water (0.25 mL). The resulting reaction mixture was degassed with nitrogen for 5 mins. Then tetrakis(triphenylphosphine)-palladium(0) (0.00738g, 0.00632 mmol 0.050 equiv.) was added. The reaction mixture was heated under microwave irradiationat 80 °C for 2.5 hours. The mixture was diluted with water and extracted with ethyl acetate. The organiclayer was dried over sodium sulfate, filtered and concentrated under reduced pressure to afford methyl N-[4-[2-[(4-fluoro-3-methoxy-phenyl)-methyl-carbamoyl]thieno[2,3-c]pyridin-4-yl]phenyl]carbamate (Compound 2) as an off-white solid. LC-MS (method B): Rt 1.08 min, m / z = 466 [M+H]+1H-NMR (400 MHz, DMSO-d6, ppm) δ = 3.39 (m, 3 H), 3.73 (s, 3 H), 3.79 (s, 3 H), 6.91 - 6.99 (m, 2 H),7.19 - 7.28 (m, 3 H), 7.42 (dd, J = 7.82, 2.44 Hz, 1 H), 7.60 (d, J = 8.50 Hz, 2 H), 8.42 (s, 1 H), 9.19 (s,1 H), 9.92 (s, 1 H). Example 3: methyl N-[5-[2-[(4-cyano-3-methoxy-phenyl)-methyl-carbamoyl]thieno[2,3-c]pyridin- 4-yl]-2-pyridyl]carbamate (Compound 3) (Compound 3) Step A: Preparation of 4-bromo-N-(4-cyano-3-methoxy-phenyl)-N-methyl-thieno[2,3-c]pyridine-2- carboxamidea [2,3-c]pyridine-2-carboxylic acid (Compound X-2) (0.300 g, 1.16 mmol)in pyridine (3.0 mL) was added 2-methoxy-4-(methylamino)benzonitrile (0.207 g, 1.278 mmol, 1.10 equiv.) and 1-propanephosphonic anhydride (50% in ethyl acetate) (2.22 g, 3.49 mmol, 3.00 equiv.) dropwise at 65 °C under N2. The mixture was heated at 65 °C for 2 hours. The reaction mixture was diluted with saturated aqueous NaHCO3 solution and extracted with ethyl acetate. The combined organic layers were washed with water, dried with sodium sulfate, filtered and concentrated under vacuum. The residue was purified by silica gel column chromatography (eluting with dichloromethane / methanol) to give 4-bromo-N-(4-cyano-3-methoxy-phenyl)-N-methyl-thieno[2,3-c]pyridine-2-carboxamide. LC-MS (method A): Rt 1.26 min, m / z = 403 [M+H]+1H-NMR (400 MHz, DMSO-d6, ppm) δ = 9.24 (s, 1 H), 8.60 (s, 1 H), 7.78 (d, J = 8.2 Hz, 1 H), 7.50 (d,J = 1.4 Hz, 1 H), 7.20 (s, 1 H), 7.16 (dd, J = 8.2, 1.6 Hz, 1 H), 3.86 (s, 3 H), 3.47 (s, 3 H). Step B: Preparation of methyl N-[5-[2-[(4-cyano-3-methoxy-phenyl)-methyl-carbamoyl]thieno[2,3- c]pyridin-4-yl]-2-pyridyl]carbamate (Compound 3) To a solution of 4-bromo-N-(4-cyano-3-methoxy-phenyl)-N-methyl-thieno[2,3-c]pyridine-2-carboxamide (0.200 g, 0.497 mmol) in dioxane / H2O (1:1, 4.0 mL) was added methyl N-[5-(4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl)-2-pyridyl]carbamate (0.180 g, 0.646 mmol, 1.30 equiv.), K3PO4 (0.158 g, 0.746 mmol, 1.50 equiv.) and tetrakis(triphenylphosphine)palladium(0) (0.0575 g, 0.0497 mmol, 0.10 equiv.). The mixture was stirred at 90 °C for 4 hours under N2, then concentrated under reduced pressure. The crude residue was purified by silica gel column chromatography (eluting with dichloromethane / methanol) to obtain methyl N-[5-[2-[(4-cyano-3-methoxy-phenyl)-methyl-carbamoyl]thieno[2,3-c]pyridin-4-yl]-2- pyridyl]carbamate as a white solid. LC-MS (method A): Rt 1.10 min, m / z = 474 [M+H]+1H-NMR (400 MHz, DMSO-d6, ppm) δ = 10.37 (s, 1 H), 9.26 (s, 1 H), 8.51 (s, 1 H), 8.36 (d, J = 1.8 Hz,1 H), 7.98 (d, J = 8.6 Hz, 1 H), 7.72 (d, J = 8.2 Hz, 1 H), 7.68 (dd, J = 8.6, 2.4 Hz, 1 H), 7.46 (d, J = 1.6 Hz, 1 H), 7.17 (s, 1 H), 7.10 (dd, J = 8.2, 1.8 Hz, 1 H), 3.85 (s, 3 H), 3.74 (s, 3 H), 3.43 (s, 3 H). Example 4: Preparation of methyl N-[5-[2-[(4-fluoro-3-methoxy-phenyl)-methyl-carbamoyl]-7- methyl-thieno[2,3-c]pyridin-4-yl]-2-pyridyl]carbamate (Compound 6) (Compound 6) Step A: Preparation of methyl 4-bromo-6-oxo-thieno[2,3-c]pyridine-2-carboxylate A 4- c]pyridine-2-carboxylate (Compound X-1) (0.500 g, 1.837 mmol, 1.00 equiv.) in 2-methoxy-2-methylpropan (9.1 mL) was cooled to 0 °C.3-chlorobenzenecarboperoxoic acid (2.3 g, 4.2 mmol, 2.3 equiv.) was added at 0 °C. The mixture was stirred at room temperature for24 hours. The mixture was filtered over a glass filter. The collected crystals were washed twice withmethoxy-2-methylpropan and dried under reduced pressure to afford methyl 4-bromo-6-oxo-thieno[2,3- c]pyridine-2-carboxylate. LC-MS (method C): Rt 0.67 min, m / z = 288 [M+H]+1H-NMR (400 MHz, CDCl3, ppm) δ = 4.01 (s, 3 H), 8.07 (s, 1 H), 8.30 - 8.44 (m, 1 H), 8.57 - 8.71 (m, 1H). Step B: Preparation of methyl 4-bromo-7-chloro-thieno[2,3-c]pyridine-2-carboxylate 4- 6-oxo- c]pyridine-2-carboxylate (0.455 g, 1.57 mmol) was suspended in phosphoryl trichloride (17.0 mL). The mixture was heated for 2 hours at reflux. The mixture was then cooled to room temperature and very slowly poured into ice / water. Crystals were collected via filtration and then dried under reduced pressure to provide methyl 4-bromo-7-chloro-thieno[2,3-c]pyridine-2- carboxylate. LC-MS (method C): Rt 1.13 min, m / z = 306 [M+H]+1H-NMR (400 MHz, CDCl3, ppm) δ = 4.04 (s, 3 H) 8.18 (s, 1 H) 8.46 (s, 1 H). Step C: Preparation of 4-bromo-7-chloro-thieno[2,3-c]pyridine-2-carboxylic acid a 4-bromo-7-chloro-thieno[2,3-c]pyridine-2-carboxylate (1.00 g, 3.25 mmol) intetrahydrofuran / H2O (1:1, 80.0 mL) was added lithium hydroxide (0.236 g, 9.78 mmol, 3.00 equiv.). Themixture was stirred at room temperature for 15 min. Then the organic solvent was removed under reduced pressure. The aqueous solution was adjusted to pH 2-3 with 2N HCl. The precipitate was collected by filtration, washed with water to provide 4-bromo-7-chloro-thieno[2,3-c]pyridine-2-carboxylic acid as a white solid. LC-MS (method C): Rt 0.86 min, m / z = 292 [M+H]+1H-NMR (400 MHz, DMSO-d6, ppm) δ = 7.98 - 8.14 (m, 1 H), 8.50 - 8.74 (m, 1 H), 13.38 - 14.98 (m, 1H). Step D: Preparation of 4-bromo-7-chloro-N-(4-fluoro-3-methoxy-phenyl)-N-methyl-thieno[2,3-c]pyridine- 2-carboxamide 7-chloro-thieno[2,3-c]pyridine-2-carboxylic acid (300 mg, 1.02 mmol), 4- fluoro-3-methoxy-N-methyl-aniline (0.238 g, 1.53 mmol, 1.50 equiv.) and N-ethyl-N-isopropyl-propan-2- amine (2.37 mL, 13.8 mmol, 5.00 equiv.) in N,N-dimethylacetamide (6.1 mL) was added 1- propanephosphonic anhydride (50% in ethyl acetate) (1.52 mL, 2.56 mmol, 2.50 equiv.) and N-ethyl-N- isopropyl-propan-2-amine (0.896 mL, 5.12 mmol, 5.00 equiv.). The reaction mixture was stirred at 50 °C for 30 minutes. The reaction mixture was concentrated under reduced pressure and then addeddropwise to a water / ice mixture. The solid was filtered and dried under reduced pressure to afford 4-bromo-7-chloro-N-(4-fluoro-3-methoxy-phenyl)-N-methyl-thieno[2,3-c]pyridine-2-carboxamide. LC-MS (method C): Rt 1.13 min, m / z = 429 [M+H]+1H-NMR (400 MHz, CDCl3, ppm) δ = 3.42 (s, 3 H), 3.81 (s, 3 H), 6.90 - 7.05 (m, 1 H), 7.08 (br dd, J =4.00, 2.54 Hz, 1 H), 7.32 (dd, J = 11.44, 8.54 Hz, 1 H), 7.47 (dd, J = 7.81, 2.36 Hz, 1 H), 8.50 (s, 1 H). Step E: Preparation of methyl N-[5-[7-chloro-2-[(4-fluoro-3-methoxy-phenyl)-methyl- carbamoyl]thieno[2,3-c]pyridin-4-yl]-2-pyridyl]carbamate N-(4-fluoro-3-methoxy-phenyl)-N-methyl-thieno[2,3-c]pyridine-2- carboxamide (0.370 g, 0.861 mmol), methyl N-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridyl]carbamate (0.264 g, 0.904 mmol, 1.05 equiv.) and cesium carbonate (0.841 g, 2.58 mmol, 3.00equiv.) in 2-methyltetrahydrofuran (6.8 mL) and water (1.7 mL) was flushed with argon for 5 min. Tetrakis(triphenylphosphine)palladium(0) (0.0503 g, 0.0430 mmol, 0.050 equiv.) was then added and the reaction mixture was heated at 80 °C for 2 hours. The reaction mixture was cooled down to room temperature and concentrated under reduced pressure. The residue was suspended with methanol and poured on water / ice. The solid was filtered and dried under reduced pressure. The crude residue was suspended in methanol and stirred at 40 °C for 30 min. The solid was filtered and dried under reduced pressure to afford methyl N-[5-[7-chloro-2-[(4-fluoro-3-methoxy-phenyl)-methyl-carbamoyl]thieno[2,3- c]pyridin-4-yl]-2-pyridyl]carbamate as a light yellow solid. LC-MS (method C): Rt 1.05 min, m / z = 501 [M+H]+1H-NMR (400 MHz, CDCl3, ppm) δ = 3.49 (s, 3 H), 3.85 (s, 3 H), 3.89 (s, 3 H), 6.79 – 6.85 (m, 1 H), 6.86- 6.89 (m, 1 H), 7.06 (s, 1 H), 7.11 - 7.17 (m, 1 H), 7.57 - 7.62 (m, 1 H), 7.75 - 7.84 (m, 1 H), 8.10 - 8.15(m, 1 H), 8.24 (s, 2 H). Step G: Preparation of methyl N-[5-[2-[(4-fluoro-3-methoxy-phenyl)-methyl-carbamoyl]-7-methyl- thieno[2,3-c]pyridin-4-yl]-2-pyridyl]carbamate (Compound 6) To a solution of methyl N-[5-[7-chloro-2-[(4-fluoro-3-methoxy-phenyl)-methyl-carbamoyl]thieno[2,3- c]pyridin-4-yl]-2-pyridyl]carbamate (0.100 g, 0.199 mmol) in 2-methyltetrahydrofuran (1.59 mL) was added potassium carbonate (0.0551 g, 0.399 mmol, 2.00 equiv.), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (CAS 95464-05-4) (0.0163 g, 0.0199 mmol, 0.100 equiv.) and 2,4,6-trimethyl-1,3,5,2,4,6-trioxatriborinane (0.0378 g,0.299 mmol, 1.50 equiv.). The mixture was stirred at 90 °C for 18h. The resulting mixture wasconcentrated under reduced pressure. The residue was suspended in methanol and filtered. The filtrate was concentrated under reduced pressure and purified by reversed phase column chromatography (eluting with acetonitrile / water) to obtain methyl N-[5-[2-[(4-fluoro-3-methoxy-phenyl)-methyl- carbamoyl]-7-methyl-thieno[2,3-c]pyridin-4-yl]-2-pyridyl]carbamate as an off-white solid. LC-MS (method C): Rt 0.82 min, m / z = 481 [M+H]+1H-NMR (400 MHz, CDCl3, ppm) δ = 2.78 (s, 3 H), 3.47 - 3.55 (m, 3 H), 3.82 - 3.86 (m, 3 H), 3.89 (s, 3H), 6.79 - 6.96 (m, 2 H), 6.98 – 7.08 (m, 1 H), 7.10 - 7.18 (m, 1 H), 7.54 - 7.64 (m, 1 H), 7.79 - 7.91 (m,1 H), 8.06 - 8.16 (m, 1 H), 8.21 - 8.27 (m, 1 H), 8.33 - 8.41 (m, 1 H). Example 5: Preparation of methyl N-[5-[2-[cyanomethyl-(4-fluoro-3-methoxy- phenyl)carbamoyl]thieno[2,3-c]pyridin-4-yl]-2-pyridyl]carbamate (Compound 11) g, was in acetonitrile (21.0 mL). 2- bromoacetonitrile (0.78 mL, 11.0 mmol, 1.05 equiv.), sodium iodide (0.800 g, 5.30 mmol, 0.50 equiv.)and potassium carbonate (1.80 g, 5.3 mmol, 1.2 equiv.) were added to this solution. The resultingsuspension was stirred at reflux for 20 hours. The mixture was diluted with acetone, the precipitate was filtered off, and the filtrate was concentrated under reduced pressure. The residue was diluted with ethylacetate and extracted with aqueous saturated sodium bicarbonate solution. The organic layer was driedover sodium sulfate, filtered and concentrated under reduced pressure. The crude residue was purified over silica gel cartridge (cyclohexane / ethyl acetate) to afford 2-(4-fluoro-3-methoxy-anilino)acetonitrile. LC-MS (method C): Rt 0.71 min, m / z = 181 [M+H]+1H-NMR (400 MHz, CDCl3, ppm) δ = 3.79 - 3.85 (m, 1 H), 3.86 (s, 3 H) ,4.07 (d, J = 6.90 Hz, 2 H),6.40 - 6.49 (m, 1 H), 6.51 - 6.60 (m, 1 H), 6.87 - 6.98 (m, 1 H).Step B: Preparation of 4-bromo-N-(cyanomethyl)-N-(4-fluoro-3-methoxy-phenyl)thieno[2,3-c]pyridine- 2-carboxamidebromothieno[2,3-c]pyridine-2-carboxylic acid (Compound X-2) (300 mg, 1.02 mmol,1.10 equiv.), 2-(4-fluoro-3-methoxy-anilino)acetonitrile (0.116 g, 0.579 mmol) and N-ethyl-N-isopropyl- propan-2-amine (0.397 mL, 2.32 mmol, 4.00 equiv.) in ethyl acetate (2.3 mL) was added 1- propanephosphonic anhydride (50% in ethyl acetate) (0.380 mL, 0.637 mmol, 1.10 equiv.). The reaction mixture was stirred at 80 °C for 17 hours. The reaction mixture was diluted with ethyl acetate and quenched with a saturated solution of sodium carbonate. The combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified over silica gel cartridge (cyclohexane / ethyl acetate) to afford 4-bromo-N-(cyanomethyl)-N-(4-fluoro-3- methoxy-phenyl)thieno[2,3-c]pyridine-2-carboxamide as an off-white solid. LC-MS (method C): Rt 0.97 min, m / z = 420 [M+H]+1H-NMR (400 MHz, CDCl3, ppm) δ = 3.92 (s, 3 H), 4.79 (s, 2 H), 6.94 - 7.10 (m, 2 H), 7.20 - 7.28 (m, 1H), 7.52 (s, 1 H), 8.60 (s, 1 H), 8.97 (s, 1 H). Step C: Preparation of methyl N-[5-[2-[cyanomethyl-(4-fluoro-3-methoxy-phenyl)carbamoyl]thieno[2,3- c]pyridin-4-yl]-2-pyridyl]carbamate (compound 11) A mixture of 4-bromo-N-(cyanomethyl)-N-(4-fluoro-3-methoxy-phenyl)thieno[2,3-c]pyridine-2- carboxamide (0.100 g, 0.237 mmol), methyl N-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2- pyridyl]carbamate (0.0992 g, 0.356 mmol, 1.50 equiv.) and sodium carbonate (0.356 mL, 0.713 mmol, 3.00 equiv.) in acetonitrile (1.42 mL) and water (0.71 mL) was flushed with argon for 5 min. Xphos Pd G2 (CAS 1310584-14-5) (0.0187 g, 0.0237 mmol, 0.10 equiv.) was then added and the reaction mixture was heated under microwave irradiation at 100 °C for 10 minutes. The reaction mixture was cooled down to room temperature and then water was added. The aqueous layer was extracted with ethyl acetate and the combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified over a silica gel cartridge (cyclohexane / ethyl acetate) to afford methyl N-[5-[2-[cyanomethyl-(4-fluoro-3-methoxy- phenyl)carbamoyl]thieno[2,3-c]pyridin-4-yl]-2-pyridyl]carbamate as a light brown solid. LC-MS (method C): Rt 0.87 min, m / z = 492 [M+H]+1H-NMR (400 MHz, CDCl3, ppm) δ = 3.90 (s, 6 H), 4.71 - 4.84 (m, 2 H), 6.94 - 6.99 (m, 1 H), 6.99 - 7.02(m, 1 H), 7.19 - 7.26 (m, 1 H), 7.36 - 7.39 (m, 1 H), 7.50 - 7.56 (m, 1 H), 7.64 - 7.72 (m, 1 H), 8.09 - 8.20(m, 1 H), 8.25 - 8.32 (m, 1 H), 8.50 (s, 1 H), 9.06 - 9.13 (m, 1 H).Example 6: Preparation of methyl N-[5-[2-[(4-fluoro-3-methoxy-phenyl)-methyl-carbamoyl]-3- methyl-thieno[2,3-c]pyridin-4-yl]-2-pyridyl]carbamate (Compound 12) (Compound 12) Step A: Preparation of 4-bromo-3-methyl-thieno[2,3-c]pyridine-2-carboxylic acid a 4-bromo-3-methyl-thieno[2,3-c]pyridine-2-carboxylate (1.00 g, 3.49 mmol, 1.0equiv.) in tetrahydrofuran (8.7 mL) and water (8.7 mL) was added lithium hydroxide (0.253 g, 10.48mmol, 3.00 equiv.). The mixture was stirred at room temperature for 15 minutes. Then the organic solvent was removed under reduced pressure. The aqueous solution was adjusted to pH 2-3 with 2N HCl. The precipitate was collected by filtration, washed with water to provide 4-bromothieno[2,3- c]pyridine-2-carboxylic acid. LC-MS (method C): Rt 0.77 min, m / z = 272 [M+H]+1H-NMR (400 MHz, DMSO-d6, ppm) δ = 3.01 (s, 3 H), 8.67 (s, 1 H), 9.28 (s, 1 H), 13.36 – 14.92 (br s, 1H). Step B: Preparation of 4-bromo-N-(4-fluoro-3-methoxy-phenyl)-N,3-dimethyl-thieno[2,3-c]pyridine-2- carboxamide a thieno[2,3-c]pyridine-2-carboxylic acid (304 mg, 1.12 mmol), 4-fluoro- 3-methoxy-N-methyl-aniline (274 mg, 1.68 mmol, 1.50 equiv.) and N-ethyl-N-isopropyl-propan-2-amine (0.976 mL, 5.59 mmol, 5.00 equiv.) in N,N-dimethylacetamide (6.7 mL) was added 1- propanephosphonic anhydride (50% in ethyl acetate) (1.66 mL, 2.79 mmol, 2.50 equiv.). The reaction mixture was stirred at 50 °C for 30 minutes. The reaction mixture was diluted with ethyl acetate and quenched with a saturated solution of sodium carbonate. The combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified over silica gel cartridge (cyclohexane / ethyl acetate) to afford 4-bromo-N-(4-fluoro-3-methoxy-phenyl)-N,3- dimethyl-thieno[2,3-c]pyridine-2-carboxamide. LC-MS (method C): Rt 0.98 min, m / z = 409 [M+H]+1H-NMR (400 MHz, CDCl3, ppm) δ = 2.67 (s, 3 H), 3.52 (s, 3 H), 3.79 (s, 3 H), 6.66 - 6.80 (m, 2 H),6.97 (br t, J = 9.45 Hz, 1 H), 8.57 (s, 1 H), 8.87 (s, 1 H). Step C: Preparation of methyl N-[5-[2-[(4-fluoro-3-methoxy-phenyl)-methyl-carbamoyl]-3-methyl- thieno[2,3-c]pyridin-4-yl]-2-pyridyl]carbamate (compound 12) A mixture of 4-bromo-N-(4-fluoro-3-methoxy-phenyl)-N,3-dimethyl-thieno[2,3-c]pyridine-2-carboxamide (0.290 g, 0.709 mmol), methyl N-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridyl]carbamate (0.228 g, 0.779 mmol, 1.10 equiv.) and cesium carbonate (0.693 g, 2.13 mmol, 3.0 equiv.) in 2- methyltetrahydrofuran (5.6 mL) and water (1.42 mL) was flushed with argon for 5 min. Tetrakis(triphenylphosphine)palladium(0) (0.0414 g, 0.0354 mmol, 0.050 equiv.) was then added and the reaction mixture was heated at 80 °C for 3 hours. The reaction mixture was cooled down to room temperature and then water was added. The aqueous layer was extracted with ethyl acetate and the combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified over a silica gel cartridge (eluting with cyclohexane / ethyl acetate) to afford methyl N-[5-[2-[(4-fluoro-3-methoxy-phenyl)-methyl-carbamoyl]-3- methyl-thieno[2,3-c]pyridin-4-yl]-2-pyridyl]carbamate as a yellow solid. LC-MS (method C): Rt 0.85 min, m / z = 481 [M+H]+1H-NMR (400 MHz, DMSO-d6, ppm) δ = 1.80 (s, 3 H), 3.39 (s, 3 H), 3.70 - 3.74 (m, 6 H), 6.80 - 6.89 (m,1 H), 7.08 - 7.16 (m, 1 H), 7.19 (dd, J = 7.81, 2.36 Hz, 1 H), 7.75 (br d, J = 7.27 Hz, 1 H), 7.94 (d, J =7.99 Hz, 1 H), 8.17 - 8.24 (m, 1 H), 8.26 (s, 1 H), 9.20 (s, 1 H), 10.39 (s, 1 H).Example 7: methyl N-[5-[2-[(4-fluoro-3-methoxy-phenyl)-methyl-carbamoyl]thieno[2,3-c]pyridin- 4-yl]-2-pyridyl]carbamate (Compound 14) O S N (Compound 14) A mixture of 4-bromo-N-(4-fluoro-3-methoxy-phenyl)-N-methyl-thieno[2,3-c]pyridine-2-carboxamide (Compound X-3) (0.300 g, 0.759 mmol), methyl N-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2- pyridyl]carbamate (0.244 g, 0.835 mmol, 1.10 equiv.) and cesium carbonate (0.742 g, 2.28 mmol, 3.00 equiv.) in 2-methyltetrahydrofuran (6.07 mL) and water (1.52 ml) was flushed with argon for 5 min. Tetrakis(triphenylphosphine)palladium(0) (0.0443 g, 0.0380 mmol, 0.050 equiv.) was then added and the reaction mixture was heated at 80 °C for 5 hours. The reaction mixture was cooled down to room temperature and diethyl ether was added. The solid was filtered, washed with diethyl ether and dried under reduced pressure at 60 °C. The solid was then dissolved in ethyl acetate and water and the aqueous layer was extracted with ethyl acetate. The precipitate that formed was filtered, washed with cyclohexane and dried under reduced pressure at 60°C to afford methyl N-[5-[2-[(4-fluoro-3-methoxy- phenyl)-methyl-carbamoyl]thieno[2,3-c]pyridin-4-yl]-2-pyridyl]carbamate as a white solid. LC-MS (method C): Rt 0.86 min, m / z = 467 [M+H]+1H-NMR (400 MHz, DMSO-d6, ppm) δ = 3.39 (s, 3 H), 3.75 (s, 3 H), 3.78 (s, 3 H), 6.92 - 7.01 (m, 2 H),7.22 (dd, J = 11.26, 8.36 Hz, 1 H), 7.40 (dd, J = 7.81, 2.36 Hz, 1 H), 7.62 - 7.69 (m, 1 H), 7.98 (d, J =8.72 Hz, 1 H), 8.37 (d, J = 2.18 Hz, 1 H), 8.50 (s, 1 H), 9.24 (s, 1 H), 10.40 (s, 1 H). Example 8: 4-(4-acetamidophenyl)-N-(4-cyano-3-methoxy-phenyl)-N-methyl-thieno[2,3-c]pyridine-2-carboxamide (Compound 33)(Compound 33) To a solution of 4-bromo-N-(4-cyano-3-methoxy-phenyl)-N-methyl-thieno[2,3-c]pyridine-2-carboxamide (as prepared in example 3, step A) (0.019 g, 0.047 mmol) in acetonitrile / H2O (4:1, 0.5 mL) was addedmethyl 4-acetamidophenylboronic acid (commercially available, CAS 101251-09-6, 0.011 g, 0.061mmol, 1.30 equiv.), Na2CO3 (0.015 g, 0.142 mmol, 3 equiv.) and XPhos Pd G2 (CAS 1310584-14-5,0.004 g, 0.005 mmol, 0.1 equiv.). The mixture was stirred at 100 °C for 16 hours under N2, thenconcentrated under reduced pressure. The crude residue was purified by reverse phase preparativeHPLC to afford 4-(4-acetamidophenyl)-N-(4-cyano-3-methoxy-phenyl)-N-methyl-thieno[2,3-c]pyridine-2-carboxamide as a white solid.LC-MS (method E): Rt 1.04 min, m / z = 457 [M+H]+1H-NMR (400 MHz, DMSO-d6, ppm) δ = 2.11 (s, 3H), 3.44 (s, 3H), 3.86 (s, 3H), 7.07 (dd, J = 8.0, 1.8Hz, 1H), 7.11 (s, 1H), 7.22 (d, J = 8.7 Hz, 2H), 7.48 (d, J = 1.5 Hz, 1H), 7.69 – 7.75 (m, 3H), 8.45 (s,1H), 9.21 (s, 1H), 10.14 (br s, 1H). Biological examples: The fungicidal activity of the compounds of the invention have been tested as follows: Phytophthora infestans / tomato / leaf disc preventative (late blight) Tomato leaf disks are placed on water 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 ofthe fungus 1 day after application. The inoculated leaf disks are incubated at 16 °C and 75% rh under a light regime of 24 h darkness followed by 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 anappropriate level of disease damage appears in untreated check leaf disks (5 - 7 days afterapplication). The following compounds gave at least 80% control of Phytophthora infestans at 200 ppm when compared to untreated control under the same conditions, which showed extensive disease development: 1 , 2 , 3 , 6 , 9 , 11 , 14 , 32 , 33 , 36 Plasmopara viticola / grape / leaf disc preventative (late blight) Grape vine leaf disks are placed on water 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 1 day after application. The inoculated leaf disks are incubated at 19 °C and 80% 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 diseasedamage appears in untreated check leaf disks (6 - 8 days after application).The following compounds gave at least 80% control of Plasmopara viticola at 200 ppm when compared to untreated control under the same conditions, which showed extensive disease development: 1 , 2 , 3 , 6 , 11 , 12 , 14 , 26 , 32 , 33 , 36 Pythium ultimum / liquid culture (seedling damping off) Mycelia fragments and oospores 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 test compound into a microtiter plate (96-well format), the nutrient broth containing the fungal mycelia / spore mixture is added. The test plates are incubated at 24 °C and the inhibition of growth is determined photometrically 2-3 days after application. The following compounds gave at least 80% control of Pythium ultimum at 20 ppm when compared to untreated control under the same conditions, which showed extensive disease development: 1 , 2 , 3 , 4 , 11 , 12 , 14 , 20 , 26 , 30 , 32 , 33 , 34 , 36 , 37
Claims
Claims 1. A compound of formula (I)wherein Z is O or S, and preferably Z is O;A1 is CH or N;A1aare independently CR1or N, with the proviso that no more than one A1ais N, and preferably two A1aare CR1; A1bis CR1or N; R1are independently selected from hydrogen, halogen, CN, C1-6alkyl, and C3-6cycloalkyl; A2are independently CR2or N, with the proviso that no more than three A2are N, preferably no more than two A2are N, preferably no more than one A2is N, and more preferably the four A2are CR2; R2are independently selected from hydrogen, hydroxy, halogen, CN, C1-6alkyl, C1-6alkoxy, C1-6alkoxy- C1-6alkyl, C1-6alkoxy-C1-6alkoxy, C2-6alkenyl, C2-6alkynyl, C3-6cycloalkyl, C3-6cycloalkyl-C1-6alkyl, C1- 6alkylsulfanyl, C1-6alkylsulfinyl, C1-6alkylsulfonyl, C1-6alkoxycarbonyl, C1-6alkylaminocarbonyl, diC1- 6alkylaminocarbonyl, and C1-6alkylcarbonyl, wherein each of the C1-6alkyl, C1-6alkoxy, C1-6alkoxy-C1- 6alkyl, C1-6alkoxy-C1-6alkoxy, C2-6alkenyl, C2-6alkynyl, C3-6cycloalkyl, C3-6cycloalkyl-C1-6alkyl, C1- 6alkylsulfanyl, C1-6alkylsulfinyl, C1-6alkylsulfonyl, C1-6alkoxycarbonyl, C1-6alkylaminocarbonyl, diC1- 6alkylaminocarbonyl, and C1-6alkylcarbonyl groups is optionally substituted with one to three substituents independently selected from halogen, hydroxy, and CN; A3is CR3or N; R3is selected from hydrogen, hydroxy, halogen, CN, C1-6alkyl, C1-6alkoxy, C1-6alkoxy-C1-6alkyl, C1- 6alkoxy-C1-6alkoxy, C2-6alkenyl, C2-6alkynyl, C3-6cycloalkyl, C3-6cycloalkyl-C1-6alkyl, C1-6alkylsulfanyl, C1-6alkylsulfinyl, C1-6alkylsulfonyl, C1-6alkoxycarbonyl, amino, C1-6alkylamino, diC1-6-alkylamino, and C3-6cycloalkylamino, wherein each of the C1-6alkyl, C1-6alkoxy, C1-6alkoxy-C1-6alkyl, C1-6alkoxy-C1-6alkoxy, C2-6alkenyl, C2-6alkynyl, C3-6cycloalkyl, C3-6cycloalkyl-C1-6alkyl, C1-6alkylsulfanyl, C1-6alkylsulfinyl, C1-6alkylsulfonyl, C1-6alkoxycarbonyl, amino, C1-6alkylamino, diC1-6-alkylamino, and C3-6cycloalkylaminogroups is optionally substituted with one to three substituents independently selected from halogen, hydroxy, and CN; R4is selected from C1-6alkyl, C1-6alkoxy-C1-6alkyl, C3-6cycloalkyl, C3-6cycloalkyl-C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C1-6alkoxy, C1-6alkylsulfanyl-C1-6alkyl, C1-6alkylsulfinyl-C1-6alkyl, C1-6alkylsulfonyl-C1-6alkyl, C1-6alkoxycarbonyl-C1-6alkyl, C1-6alkylaminocarbonyl-C1-6alkyl, diC1-6alkylaminocarbonyl-C1-6alkyl, and CN, wherein each of the C1-6alkyl, C1-6alkoxy-C1-6alkyl, C3-6cycloalkyl, C3-6cycloalkyl-C1-4alkyl, C2- 6alkenyl, C2-6alkynyl, C1-6alkoxy, C1-6alkylsulfanyl-C1-6alkyl, C1-6alkylsulfinyl-C1-6alkyl, C1-6alkylsulfonyl- C1-6alkyl, C1-6alkoxycarbonyl-C1-6alkyl, C1-6alkylaminocarbonyl-C1-6alkyl and diC1-6alkylaminocarbonyl- C1-6alkyl groups is optionally substituted with one to three substituents independently selected from halogen and CN; wherein A3and R4taken together optionally form a ring, preferably a 5-8-membered heterocycle, and more preferably a 6-membered heterocycle; and R5is selected from C1-6alkyl, C1-6alkoxy, C3-6cycloalkyl, C3-6cycloalkyl-C1-6alkyl, C1-6alkoxyC1-6alkyl, C1- 6alkylamino, diC1-6alkylamino, and C1-6alkylC1-6alkoxyamino, wherein each of said groups is optionally substituted with one to three substituents independently selected from halogen and CN; or a salt or N-oxide thereof.
2. The compound according to claim 1, wherein R2are independently selected from hydrogen, hydroxy, halogen, CN, C1-6alkyl, C1-6alkoxy, C1-6alkoxy-C1-6alkyl, C1-6alkoxy-C1-6alkoxy, C1-6alkoxycarbonyl, C1- 6alkylaminocarbonyl, diC1-6alkylaminocarbonyl, and C1-6alkylcarbonyl, wherein each of the C1-6alkyl, C1- 6alkoxy, C1-6alkoxy-C1-6alkyl, C1-6alkoxy-C1-6alkoxy, C1-6alkoxycarbonyl, C1-6alkylaminocarbonyl, diC1- 6alkylaminocarbonyl, and C1-6alkylcarbonyl groups is optionally substituted with one to three substituents independently selected from halogen, hydroxy, and CN.
3. The compound according to any one of the preceding claims, wherein R3is selected from hydrogen, hydroxy, halogen, CN, C1-6alkyl, C1-6alkoxy, C1-6alkoxy-C1-6alkyl, and C1-6alkoxycarbonyl, wherein each of the C1-6alkyl, C1-6alkoxy, C1-6alkoxy-C1-6alkyl, and C1-6alkoxycarbonyl groups is optionally substituted with one to three substituents independently selected from halogen, hydroxy, and CN.
4. The compound according to any one of the preceding claims, wherein four A2are CR2and A3is N.
5. The compound according to any one of the claims 1 to 4, wherein, and preferably the three A2are CR2and A3is CR3.
6. The compound according to any one of the claims 1 to 4, wherein preferably the three A2are CR2and A3is CR3.
7. The compound according to any one of the claims 1 to 4, wherein four A2are CR2and A3is CR3, and preferably .
8. The compound according to any one of the preceding claims, wherein R4 is selected from C1-6alkyl,C1-6alkoxy-C1-6alkyl, C3-6cycloalkyl, C3-6cycloalkyl-C1-4alkyl, C2-6alkenyl, C2-6alkynyl, and C1-6alkoxy, wherein each of the C1-6alkyl, C1-6alkoxy-C1-6alkyl, C3-6cycloalkyl, C3-6cycloalkyl-C1-4alkyl, C2-6alkenyl, C2- 6alkynyl, and C1-6alkoxy groups is optionally substituted with one to three substituents independently selected from halogen and CN.
9. The compound according to any one of the preceding claims, wherein R5is selected from C1-6alkyl, C1-6alkoxy, C3-6cycloalkyl, C3-6cycloalkyl-C1-6alkyl, and C1-6alkoxyC1-6alkyl, wherein each of said groups is optionally substituted with one to three substituents independently selected from halogen and CN.
10. A composition comprising a fungicidally effective amount of a compound as defined in any one ofclaims 1 to 9.
11. A composition according to claim 11, wherein the composition further comprises at least onecompound selected among an additional active ingredient, an appropriate formulation inert, a carrier, an adjuvant, and any mixtures thereof.
12. A method of combating, preventing or controlling phytopathogenic diseases which comprises applying to a phytopathogen, to the locus of a phytopathogen, to a plant susceptible to attack by aphytopathogen, or to a plant propagation material thereof, a fungicidally effective amount of a compoundaccording to any one of claims 1 to 9, or a composition comprising a compound according to any oneof claims 1 to 9, or a composition according to claim 10 or 11.
Citation Information
Patent Citations
DNA sequences encoding polypeptides having beta-1,3-glucanase activity
EP0353191A2
Novel bacillus thuringiensis isolate denoted b.t. ps81gg, active against lepidopteran pests, and a gene encoding a lepidopteran-active toxin
EP0367474A1
Insecticidal toxines, genes coding therefor, antibodies binding them, transgenic plant cells and plants expressing these toxines
EP0374753A2
Disease-resistant transgenic plants
EP0392225A2
Novel bacillus thuringiensis isolates active against lepidopteran pests, and genes encoding novel lepidopteran-active toxins
EP0401979A2