Novel bicyclic acrylyl compounds as fungicide

Abstract

Novel bicyclic acrylyl compounds as fungicide (I) wherein, W, R1, R2, R3, R4, R5 and R6 are as defined in detailed description. The present invention further discloses methods for their preparation and the use of the compounds of formula (I) as a fungicide.

Description

[0001] Title: NOVEL BICYCLIC ACRYLYL COMPOUNDS AS FUNGICIDE

[0002] FIELD OF THE INVENTION

[0003] The present invention relates to compounds of formula (I). More particularly, the present invention relates to novel bicyclic acrylyl compounds of formula (I), and to a process for the preparation thereof. The present invention further relates to compositions and combinations comprising compounds of formula (I), and to their use in agriculture or horticulture for controlling or preventing infestation of plants, harvested food crops, seeds or non-living materials by harmful pest, preferably by controlling phytopathogenic microorganisms, such as fungi.

[0004] BACKGROUND OF THE INVENTION

[0005] W02001000562 and EP0212859 disclose methoxyacrylate compounds with fungicidal activity.

[0006] However, there is a constant need for new fungicides with broader spectrum of efficacy, longer-lasting activity, better environmental safety, as well as a low risk of resistance development.

[0007] Accordingly, it is an objective of the present invention to provide alternate compounds with improved / enhanced activity and / or a broader efficacy spectrum against phytopathogenic microorganisms, such as fungi.

[0008] This objective is achieved by novel bicyclic acrylyl compounds of formula (I) and their use in agriculture or horticulture for controlling or preventing infestation of plants, harvested food crops, seeds, or non-living materials by phytopathogenic microorganisms, preferably fungi.

[0009] SUMMARY OF INVENTION

[0010] Accordingly, the present invention provides novel bicyclic acrylyl compounds of formula (I) or salts, stereoisomers, tautomers, polymorphs or N-oxides thereof.

[0011]

[0012] wherein, W, R1, R2, R3, R4, R5and R6are as defined in the detailed description.

[0013] In one embodiment, the present invention provides a process for preparing compounds of formula (I) or salts or stereoisomers, tautomers, polymorphs or N-oxides thereof. In another embodiment, the present invention provides compositions for controlling or preventing phytopathogenic microorganisms, preferably fungi, comprising a biologically effective amount of the compound of formula (I) or salts, stereoisomers, tautomers, polymorphs or N-oxides thereof and an additional agrochemically acceptable auxiliaries.

[0014] In yet another embodiment, the present invention provides compositions that further comprise at least one additional biologically active and compatible compound selected from fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, safeners, plant growth regulators, antibiotics, fertilizers, or nutrients.

[0015] In yet another embodiment, the present invention provides the use of compounds of formula (I), or salts, stereoisomers, tautomers, polymorphs or N-oxides thereof as a fungicide.

[0016] In yet another embodiment, the present invention provides fungicidal compositions which comprise compounds of formula (I) that can be used to curatively or preventively control phytopathogenic fungi of plants or crops.

[0017] In yet another embodiment, the present invention provides a method for curatively or preventively controlling phytopathogenic fungi of plants or crops characterized in that a compound of formula (I) or a fungicidal composition according to the invention is applied to the seed, the plant or the fruit of the plant or the soil wherein the respective plant is growing or wherein it is desired to grow.

[0018] In yet another embodiment, the compounds of formula (I) according to the present invention may be useful for combating phytopathogenic fungi containing a mutation in the mitochondrial cytochrome b conferring resistance to Qo inhibitors (e.g strobilurins such as azoxystrobin, pyraclostrobin, picoxystrobin and trifloxystrobin or fenamidone or famoxadone).

[0019] In yet another embodiment, the compounds of formula (I) according to the present invention may be useful for combating phytopathogenic fungi containing a mutation in the mitochondrial cytochrome b conferring resistance to Qo inhibitors (e.g strobilurins such as azoxystrobin, pyraclostrobin, picoxystrobin and trifloxystrobin or fenamidone or famoxadone), wherein the mutation is G143A. In yet another embodiment, the present invention provides the use of compounds of formula (I) against resistant soybean rust fungi having an amino acid substitution of F129L in the mitochondrial cytochrome b protein.

[0020] DETAILED DESCRIPTION OF THE INVENTION DEFINITIONS:

[0021] The definitions provided herein for the terminologies used in the present disclosure are for illustrative purpose only and in no manner limit the scope of the present invention disclosed in the present disclosure. As used herein, the terms “comprises”, “comprising”, “includes”, “including”, “has”, “having”, “contains”, “containing”, “characterized by” or any other variation thereof, are intended to cover a nonexclusive inclusion, subject to any limitation explicitly indicated. For example, a composition, mixture, process or method that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such composition, mixture, process or method.

[0022] The transitional phrase “consisting of’ excludes any element, step or ingredient not specified. If in the claim, such would close the claim to the inclusion of materials other than those recited, except for impurities ordinarily associated therewith. When the phrase “consisting of’ appears in a clause of the body of a claim, rather than immediately following the preamble, it limits only the element set forth in that clause; other elements are not excluded from the claim as a whole.

[0023] Further, unless expressly stated to the contrary, “or” refers to an inclusive “or” and not to an exclusive “or”. For example, a condition A “or” B is satisfied by any one of the following: A is true (or present) and B is false (or not present), A is false (or not present) and B is true (or present), and both A and B are true (or present).

[0024] Also, the indefinite articles “a” and “an” preceding an element or component of the present invention are intended to be nonrestrictive regarding the number of instances (i.e. occurrences) of the element or component. Therefore, “a” or “an” should be read to include one or at least one, and the singular word form of the element or component also includes the plural unless the number is obviously meant to be singular.

[0025] As referred to in this disclosure, the term “invertebrate pests” includes but is not limited to fungi, stramenopiles (oomycetes), bacteria, nematodes, mites, ticks, insects and nematodes of economic importance.

[0026] In the context of this disclosure, “pest control” means inhibition of invertebrate pest development (including necrosis, retarded growth and / or death), and related expressions are defined analogously. The term “agriculture” or “agronomic” refers to the production of field crops such as for food, feed and fiber and includes the growth of com, soybeans and other legumes, rice, cereal (e.g., wheat, oats, barley, rye, rice, maize), leafy vegetables (e.g., lettuce, cabbage, and other cole crops), fruiting vegetables (e.g., tomatoes, pepper, eggplant, crucifers and cucurbits), potatoes, sweet potatoes, grapes, cotton, tree fruits (e.g., pome, stone and citrus), small fruit (berries, cherries) and other specialty crops (e.g., canola, sunflower, olives).

[0027] The term “nonagronomic” refers to other than field crops, such as horticultural crops (e.g., greenhouse, nursery or ornamental plants not grown in a field), residential, agricultural, commercial and industrial structures, turf (e.g., sod farm, pasture, golf course, lawn, sports field, etc.), wood products, stored product, agro-forestry and vegetation management, public health (i.e. human) and animal health (e.g., domesticated animals such as pets, livestock and poultry, undomesticated animals such as wildlife) applications.

[0028] Nonagronomic applications include protecting an animal from an invertebrate parasitic pest by administering a parasiticidally effective (i.e., biologically effective) amount of a compound of the present invention, typically in the form of a composition formulated for veterinary use, to the animal to be protected. As referred to in the present disclosure and claims, the terms “parasiticidal” and “parasiticidally” refer to observable effects on an invertebrate parasite pest to provide protection of an animal from the pest. Parasiticidal effects typically relate to diminishing the occurrence or activity of the target invertebrate parasitic pest. Such effects on the pest include necrosis, death, retarded growth, diminished mobility or lessened ability to remain on or in the host animal, reduced feeding and inhibition of reproduction. These effects on invertebrate parasite pests provide control (including prevention, reduction or elimination) of parasitic infestation or infection of the animal.

[0029] The meaning of various terms used in the description shall now be illustrated.

[0030] As used herein, the term "halogen" or “halo” refers to fluorine (fluoro), chlorine (chloro), bromine (bromo), or iodine (iodo), preferably fluorine, chlorine, or bromine.

[0031] As used herein, cyano means a -CN group.

[0032] As used herein, hydroxy or hydroxyl means a -OH group.

[0033] As used herein, oxo means a =0 group.

[0034] As used herein, thioxo means a =S group.

[0035] As used herein, the term “may” is intended to indicate an optional feature or condition, and is used interchangeably with the term “optionally.” Unless otherwise specified, the use of “may” should not be interpreted as implying uncertainty or speculation, but rather as indicating a non-mandatory aspect of the invention.

[0036] As used herein, the term "Ci-Cn-alkyl" refers to a straight or branched hydrocarbon chain radical consisting solely of carbon and hydrogen atoms, containing no unsaturation, having from one to n carbon atoms, and which is attached to the rest of the molecule by a single bond. C1-C8-alkyl, Ci-Ce-alkyl, Ci-C4-alkyl, C’l-CAalkyl and Ci-C2-alkyl are to be construed accordingly. Examples of Ci-Cn-alkyl include, but are not limited to, n-pentyl, 1 -methylbutyl, 2-methylbutyl, 3 -methylbutyl, 2, 2-dimethylpropyl, 1 -ethylpropyl, n-hexyl, 1 -dimethylpropyl, 1, 2-dimethylpropyl, 1 -methylpentyl, 2-methylpentyl, 3 -methylpentyl, 4-methylpentyl, 1 -dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 2, 2-dimethylbutyl, 2, 3 -dimethylbutyl, 3 -dimethylbutyl, 1 -ethylbutyl, 2-ethylbutyl, 1, 2 -trimethylpropyl, 1,2,2-trimethylpropyl, 1 -ethyl -1 -methylpropyl or 1 -ethyl -2 -methylpropyl, preferably methyl, ethyl, n-propyl, 1 -methylethyl, n-butyl, 1 -dimethylethyl, n-pentyl or n-hexyl. As used herein, the term "C2-Cn-alkenyl" refers to a straight or branched hydrocarbon chain radical consisting solely of carbon and hydrogen atoms, containing at least one double bond that can be of either the (E)- or (+ / -) configuration, having from two to n carbon atoms, which is attached to the rest of the molecule by a single bond. G-G, -alkenyl is to be construed accordingly. Examples of C2-C11-alkenyl include, but are not limited to, vinyl, 1 -propenyl, 2-propenyl, 1 -methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1 -methyl- 1 -propenyl, 2-methyl-l -propenyl, 1 -methyl -2 -propenyl, 2-methyl-2-propenyl, 1 -pentenyl, 2-pentenyl, 3 -pentenyl, 4-pentenyl, 1 -methyl- 1-butenyl, 2 -methyl- 1-butenyl, 3-methyl- 1-butenyl, 1 -methyl -2 -butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 2-methyl-2-butenyl, 1 -methyl -2 -butenyl, 2 -methyl -2 -butenyl, 3 -methyl -2 -butenyl, l-methyl-3 -butenyl, 2-methyl-3 -butenyl, 3 -methyl-3 -butenyl, 1 -dimethyl -2 -propenyl, 1, 2-dimethyl-l -propenyl, 1, 2-dimethyl-2-propenyl, 1-ethyl-1 -propenyl, 1 -ethyl -2 -propenyl, 1 -hexenyl, 2-hexenyl, 3 -hexenyl, 4-hexenyl, 5 -hexenyl, 1-methyl-1 -pentenyl, 2-methyl-l -pentenyl, 3 -methyl- 1 -pentenyl, 4-methyl-l -pentenyl, 1 -methyl -2-pentenyl, 2 -methyl-3 -pentenyl, 1 -methyl -2 -pentenyl, 3 -methyl- 1 -pentenyl, 3 -methyl -pentenyl, 2-methyl-pentenyl, 3 -methyl-2 -pentenyl, 3, 2-methyl-2-pentenyl, 3 -methyl -2 -pentenyl, 4-methyl-2-pentenyl, l-methyl-3 -pentenyl, 2-methyl-3-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 -dimethyl -2-butenyl, l-dimethyl-3 -butenyl, 1, 2-dimethyl-l -butenyl, 1, 2 -dimethyl -2 -butenyl, methyl -2 -pentenyl, methyl-3 -pentenyl, methyl-2-butenyl, 1, 1, 2-dimethyl-3-butenyl, 1, 3 -dimethyl- 1-butenyl, 1, 3-dimethyl-2-butenyl, 1, 3 -dimethyl-3 -butenyl, 2-dimethyl-3-butenyl, 2, 3 -dimethyl- 1-butenyl, 2, 3-dimethyl-2-butenyl, 2, 3 -dimethyl-3 -butenyl, 3 -dimethyl- 1-butenyl, 3 -dimethyl -2 -butenyl, 1-ethyl-l-butenyl, 1 -ethyl -2 -butenyl, l-ethyl-3 -butenyl, 2-ethyl-l-butenyl, 2-dimethyl-3 -butenyl, 2-dimethyl-2-butenyl, 2-ethyl-l-butenyl, 2 -dimethyl-3 -butenyl, 2-dimethyl, 2 -ethyl -2 -butenyl, 2-ethyl-3 -butenyl, 1, 2 -trimethyl -2 -propenyl, 1 -ethyl- 1 -methyl -2 -propenyl, 1 -ethyl -2-methyl-l -propenyl and 1 -ethyl -2-methyl -2 -propenyl.

[0037] As used herein, the term "C2-Cn-haloalkenyl" refers to a C2-Cn-alkenyl radical, as generally defined above, and substituted with one or more of the same or different halogen atoms.

[0038] As used herein, the term "C2-Cn-alkynyl" refers to a straight or branched hydrocarbon chain radical group consisting solely of carbon and hydrogen atoms, containing at least one triple bond, having from two to n carbon atoms, and which is attached to the rest of the molecule by a single bond. Examples of C2-Cn-alkynyl include, but are not limited to, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1 -methyl -2 -propynyl, 1 -pentynyl, 2-pentynyl, 3 -pentynyl, 4-pentynyl, 1 -methyl -2-butynyl, 1 -methyl - 3-butynyl, 2-methyl-3-butynyl, 3 -methyl- 1-butynyl, 1 -dimethyl -2 -propynyl, 1 -ethyl -2 -propynyl, 1-hexynyl, 2-hexynyl, 3 -hexynyl, 4-hexynyl, 5 -hexynyl, 1 -methyl -2 -pentynyl, l-methyl-3 -pentynyl, 1-methyl-4-pentynyl, 2-methyl-3 -pentynyl, 2-methyl-4-pentynyl, 3 -methyl- 1 -pentynyl, 3-methyl-4-pentynyl, 4-methyl-l -pentynyl, 4-methyl-2-pentynyl, 1 -dimethyl -2-butynyl, 1 -dimethyl-3 -butynyl, 1, 2-dimethyl-3-butynyl, 2-dimethyl-3-butynyl, 3-dimethyl-l-butynyl, l-ethyl-2-butynyl, l-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1 -ethyl- 1 -methyl -2 -butynyl -apropynyl group.

[0039] As used herein, the term "C2-Cn-haloalkynyl" refers to a C2-Cn-alkynyl radical, as generally defined above, and substituted with one or more of the same or different halogen atoms.

[0040] As used herein, the term “cyano-Ci-Ce -alkyl” refers to a Ci-Ce alkyl radical as generally defined above, substituted with one or more cyano groups. The term “cyano-Ci-C4-alkyl” is to be construed accordingly.

[0041] As used herein, the term "Ci-Ce-alkoxy" refers to a straight chain or branched saturated alkyl radical having one to six carbon atoms, which is attached via an oxygen atom. For example, it refers to the radical of the formula -OR where R is a Ci-Ce-alkyl radical as generally defined above. C1-C3 -alkoxy is to be construed accordingly. Examples of Ci-Ce-alkoxy include, but are not limited to, methoxy, ethoxy, propoxy, 1 -methylethoxy, butoxy, 1 -methylpropoxy, 2-methylpropoxy and 1, 1-dimethylethoxy, pentyloxy, 1 -methylbutyloxy, 2 -methylbutyloxy, 3 -methoxybutoxy, 1-dimethylpropyloxy, 1, 2-dimethylpropyloxy, 2,2-dimethylpropyloxy, 1 -ethylpropyloxy, hexyloxy, 1-methylpentyloxy, 2-methylpentyloxy, 3 -methylpentyloxy, 4-methylpentyloxy, 1 -dimethylbutyloxy, 1, 2 -dimethylbutyloxy, 1, 3 -dimethylbutyloxy, 2, 2-dimethylbutyloxy, 2, 3 -dimethylbutyloxy, 3-dimethylbutyloxy, 1 -ethylbutoxy, 2-ethylbutoxy, 1, 2-trimethylpropyloxy, 1,2, 2-trimethylpropyloxy, 1 -dimethylpropyloxy, 2-methylpropyloxy, 2-dimethylpropyloxy, 1, 1 -ethyl- 1 -methylpropoxy and 1-ethyl-2 -methylpropoxy.

[0042] As used herein, the term "Ci-Ce-haloalkyl" refers to a straight-chain or branched saturated Ci-Ce -alkyl radical, as generally defined above, substituted with one or more of the same or different halogen atoms. Ci-C4-haloalkyl or Ci-Cs-haloalkyl are to be construed accordingly. Examples of Ci-Ce-haloalkyl include but are not limited to chloromethyl, fluoromethyl, fluoroethyl, difluoromethyl, trifluoromethyl, and 2,2,2-trifluoroethyl 5 -fluoropentyl, 5 -chloropentyl, 5 -bromopentyl, 5 -iodopentyl, undecafluoropentyl, 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl, 6-iodohexyl and dodecafluorohexyl. As used herein, the term "Ci-Ce-haloalkoxy" refers to a straight-chain or branched saturated Ci-Ce-alkoxy group, as defined above, substituted with one or more of the same or different halogen atoms. Ci-C4-haloalkoxy is to be construed accordingly. Examples of Ci-Ce-haloalkoxy include, but are not limited to, i.e., for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2 -fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2, 2-difluoroethoxy, 2,2, 2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2, 2-difluoroethoxy, 2, 2-dichloro-2-fluoroethoxy, 2,2, 2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy, 3 -fluoropropoxy, 2-chloropropoxy, 3 -chloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 2, 2-difluoropropoxy, 2, 3 -difluoropropoxy, 2-bromopropoxy, 2, 3 -dichloropropoxy, 3,3, 3 -trifluoropropoxy, 3,3, 3 -trichloropropoxy, 2,3,3, 3 -pentafluoropropoxy, heptafluoropropoxy, 1- fluoromethyl -2 -fluoroethoxy, 1 -chloromethyl -2 -chloroethoxy, 1 -bromomethyl -2 -bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy and nonafluorobutoxy;.

[0043] As used herein, the term "C2-C6-alkenyloxy" refers to -OR, wherein R is the C2-C6 -alkenyl group as defined above.

[0044] As used herein, the term "C2-C6-haloalkenyloxy" refers to -OR, wherein R is the C2-C6 -alkenyl group as defined above, substituted with one or more of the same or different halogen atoms.

[0045] As used herein, the term "C2-C6-alkynyloxy" refers to -OR, wherein R is the C2-Ce-alkynyl group as defined above.

[0046] As used herein, the term "C2-C6-haloalkynyloxy" refers to -OR, wherein R is the C2-Ce-alkynyl group as defined above, substituted with one or more of the same or different halogen atoms.

[0047] As used herein, the term “Ci-Ce-alkylsulfanyl” or Ci-Ce-alkylthio refers to a radical of the formula -SR wherein R is a Ci-Ce-alkyl radical as generally defined above.

[0048] As used herein, the term “Ci-Ce-alkylsulfinyl” refers to a radical of the formula -S(O)R wherein R is a Ci-Ce-alkyl radical as generally defined above.

[0049] As used herein, the term “Ci-Ce-alkylsulfonyl” refers to a radical of the formula -S(O)2R wherein R is a Ci-Ce-alkyl radical as generally defined above.

[0050] As used herein, the term Ci-Ce-haloalkylsulfanyl" refers to a Ci-Ce-alkylsulfanyl group, as defined above, substituted with one or more of the same or different halogen atoms.

[0051] As used herein, the term Ci-Ce-haloalkylsulfinyl" refers to a Ci-Ce-alkylsulfinyl group, as defined above, substituted with one or more of the same or different halogen atoms.

[0052] As used herein, the term Ci-Ce-haloalkylsulfonyl" refers to a Ci-Ce-alkylsulfonyl group, as defined above, substituted with one or more of the same or different halogen atoms.

[0053] As used herein, the term "CACn-cycloalkyl" refers to three (3) to n membered cycloalkyl radicals. Examples include but are not limited to cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

[0054] As used herein, the term “Cs-Ce-cycloalkyloxy” refers to three (3) to six (6) membered cycloalkyloxy radicals (cycloalkyl ring attached through an oxygen atom). Examples include but are not limited to cyclopropyloxy, cyclobutyloxy and cyclopentyloxy.

[0055] As used herein, the term "C’,-Cn-cycloalkcnyl" refers to a stable, monocyclic ring radical that is partially unsaturated and contains 3 to n carbon atoms. CAC’i-c cloalkcn l is to be construed accordingly. Examples of CACe-cycloalkcnyl include but are not limited to, 1 -cyclopropenyl, 2-cyclopropenyl, 1-cyclobutenyl, 2-cyclobutenyl, 1 -cyclopentenyl, 2-cyclopentenyl, 1,3 -cyclopentadienyl, 1, 4-cyclopentadienyl, 2, 4-cyclopentadienyl, 1 -cyclohexenyl, 2-cyclohexenyl, 3 -cyclohexenyl, 1, 3-cyclohexadienyl, 1, 4-cyclohexadienyl and 2,5 -cyclohexadienyl. As used herein, the term “Cs-Ce-cycloalkyl-Ci-Cn-alkyl-” refers to a Ci-Cn-alkyl radical as generally defined above, substituted with one or more G-Ce-cycloalkyl groups as generally defined above. C3-Ce-cycloalkyl-C’i-C’, -alkyl is to be construed accordingly. Examples include but are not limited to, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclopentylethyl and cyclohexylmethyl. As used herein, the term "G-G-halocycloalkyl" refers to a G-G, -cycloalkyl radical, as generally defined above, and substituted with one or more of the same or different halogen atoms.

[0056] As used herein, the term "C’.-Ce-halocycloalkyloxy" refers to a G-G-cycloalkyloxy radical, as generally defined above, and substituted with one or more of the same or different halogen atoms. As used herein, the term “phenyl-Ci-G-alkyl-” refers to a phenyl ring attached to a Ci-Ce-alkyl radical as generally defined above, substituted with one phenyl group. Examples include but are not limited to, phenylmethyl (benzyl) and phenylethyl.

[0057] As used herein, the term “Cs-Ce-cycloalkyloxy-Ci-Ce-alkyl-” refers to a Ci-G-alkyl radical, as generally defined above, substituted with G-G-cycloalkyloxy group. Examples include but are not limited to, cyclopropyloxymethyl, cyclobutyloxymethyl, cycloprpyloxyethyl and cyclopentyloxymethyl.

[0058] As used herein, the term phenyl-Ci-Ce-alkyl refers to an alkyl group containing from one to six carbon atoms (Ci-Ce), which is directly attached to a phenyl group. The alkyl chain may be linear or branched. Examples of such groups include, but are not limited to, benzyl (phenylmethyl), phenylethyl, phenylpropyl, and corresponding higher homologues up to phenylhexyl.

[0059] As used herein, the term wherein heteroatom(s) or substituent(s) “independently” selected from means substituent(s) or heteroatom(s) can be identical or different.

[0060] The term “aryl” as used herein is a group that contains any carbon-based aromatic group, including, but not limited to phenyl, naphthalene, biphenyl, anthracene, and the like. The aryl group can be substituted or unsubstituted. In addition, the aryl group can be a single ring structure or comprises multiple ring structures that are either fused ring structures or attached via one or more bridging groups such as a carbon-carbon bond.

[0061] As used herein, unless explicitly stated otherwise, the term "hetero" in connection with rings refers to a ring in which at least one ring atom is not carbon and which can contain 1 to 4 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, provided that each ring contains no more than 4 nitrogens, no more than 2 oxygens and no more than 2 sulfurs. In general, no two oxygen atoms are adjacent within the ring.

[0062] The term "aromatic" indicates that the Huckel rule is satisfied, and the term "non-aromatic" indicates that the Huckel rule is not satisfied. The term "heterocycle" or "heterocyclic" or "heterocyclic ring system ", unless specifically defined elsewhere, includes "aromatic heterocycle" or "heteroaryl bicyclic ring system" and "nonaromatic heterocycle ring system" or polycyclic or bicyclic (spiro, fused, bridged, non-fused) ring compounds in which ring may be aromatic or non-aromatic, wherein the heterocycle ring contains at least one heteroatom selected from N, O, S(0)o-2, and or C ring member of the heterocycle may be replaced by C(=O), C(=S), C(=CR*R*) and C=NR*, * indicates integers.

[0063] As used herein, unless otherwise stated, the term "non-aromatic heterocyclyl" or "non-aromatic heterocyclic" refers to a 5- or 6-membered non-aromatic monocyclic ring which comprises 1, 2 or 3 heteroatoms, wherein the heteroatoms are individually selected from nitrogen, oxygen, and S(0)o-2. Examples of non-aromatic heterocyclyl include, but are not limited to, tetrahydrofuryl, pyrrolidinyl, pyrazolidinyl, imidazolidinyl, piperidinyl, piperazinyl, morpholinyl, dioxolanyl, dithiolanyl, oxazolidinyl, isothiazolidinyl and thiazolidinyl.

[0064] As used herein, unless otherwise stated, the term "non-aromatic carbocyclyl" or "non-aromatic carbocyclic" refers to a 4- or 6-membered non-aromatic monocyclic ring. Examples of non-aromatic carbocyclic rings include, but are not limited to, cyclobutyl, cyclopentyl and cyclohexyl.

[0065] When a compound is substituted with a substituent bearing a subscript that indicates the number of said substituents can exceed 1, said substituents (when they exceed 1) are independently selected from the defined group of substituents. Further, when the subscript m in (R)mindicates an integer ranging from, for example, 0 to 4, then the number of substituents may be selected from the integers between 0 and 4 inclusively.

[0066] When a group contains a substituent which can be hydrogen, then, when this substituent is taken as hydrogen, it is recognized that said group is being unsubstituted.

[0067] The numerical values mentioned in the description / claims, may form an essential aspect of the present invention; however, any deviation from such numerical values shall still fall within the scope of the present invention, provided that the deviation follows the same scientific principle as disclosed herein. The term “plant” is understood here to mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants may be plants that can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and the plant cultivars which are protectable and non-protectable by plant breeders’ rights.

[0068] For the present disclosure, the term “plant” includes a living organism of the kind exemplified by trees, shrubs, herbs, grasses, fems, and mosses, typically growing in a site, absorbing water and required substances through its roots, and synthesizing nutrients in its leaves by photosynthesis. Examples of “plant” for the purpose of the present invention include but are not limited to agricultural crops such as wheat, rye, barley, triticale, oats or rice; beet, e.g. sugar beet or fodder beet; fruits and fruit trees, such as pomes, stone fruits or soft fruits, e.g. apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, blackberries or gooseberries; leguminous plants, such as lentils, peas, alfalfa or soybeans; oil plants, such as rape, mustard, olives, sunflowers, coconut, cocoa beans, castor oil plants, oil palms, ground nuts or soybeans; cucurbits, such as squashes, cucumber or melons; fiber plants, such as cotton, flax, hemp or jute; citrus fruit and citrus trees, such as oranges, lemons, grapefruits or mandarins; any horticultural plants, vegetables, such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, cucurbits or paprika; lauraceous plants, such as avocados, cinnamon or camphor; cucurbitaceae; oleaginous plants; energy and raw material plants, such as cereals, com, soybean, other leguminous plants, rape, sugar cane or oil palm; tobacco; nuts; coffee; tea; cacao; bananas; peppers; vines (table grapes and grape juice grape vines); hop; turf; sweet leaf (also called Stevia); natural rubber plants or ornamental and forestry plants, such as flowers, shrubs, broadleaved trees or evergreens, e.g. conifers; and on the plant propagation material, such as seeds, and the crop material of these plants.

[0069] Preferably, the plant for the present invention includes but is not limited to cereals, com, rice, soybean and other leguminous plants, fruits and fruit trees, grapes, nuts and nut trees, citms and citrus trees, any horticultural plants, cucurbitaceae, oleaginous plants, tobacco, coffee, tea, cacao, sugarbeet, sugar cane, cotton, potato, tomato, onions, peppers and vegetables, ornamentals, any floricultural plants, and other plants for the use of humans and animals.

[0070] The term “plant parts” is understood to mean all parts and organs of plants above and below the ground. For the present disclosure, the term plant parts include but is not limited to cuttings, leaves, twigs, tubers, flowers, seeds, branches, roots including taproots, lateral roots, root hairs, root apex, root cap, rhizomes, slips, shoots, fruits, fruit bodies, bark, stem, buds, axillary buds, meristems, nodes, and internodes.

[0071] The term “locus thereof’ includes soil, surroundings of a plant or plant parts, and equipment or tools used before, during or after sowing / planting a plant or a plant part.

[0072] The term “pest” for the purpose of the present disclosure includes but is not limited to fungi, stramenopiles (oomycetes), bacteria, insects, and rodents.

[0073] A pesticide is generally a chemical or biological agent (such as a pesticidal active ingredient, compound, composition, vims, bacterium, antimicrobial, or disinfectant) that through its effect deters, incapacitates, kills, or otherwise suppresses pests. Target pests can include insects, plant pathogens, weeds, and microbes that destroy property, cause nuisance, spread disease, or are vectors for disease. The term pesticides includes also plant growth regulators that alter the growth, flowering, or reproduction rate of plants; defoliants that cause leaves or other foliage to drop from a plant, usually to facilitate harvest; desiccants that promote drying of living tissues, such as unwanted plant tops; plant activators that activate plant physiology for the defense against certain pests; safeners that reduce unwanted herbicidal action of pesticides on crop plants; and plant growth promoters that affect the plant physiology to increase plant growth, biomass, yield or any other quality parameter of the harvestable goods of a crop plant.

[0074] The term "pesticidal effective amount" denotes an amount of the composition or of the compounds of formula (I) and their mixtures, sufficient to control harmful pests on cultivated plants or in the protection of materials, not resulting in substantial damage to the treated plants. Such an amount can vary in a broad range and is dependent on various factors, such as the animal pest’s species to be controlled, the treated cultivated plant or material, the climatic conditions, and the specific mixture being used.

[0075] The term “fungicide” as used herein means a compound that controls, modifies, or prevents the growth of fungi.

[0076] The term "fungicidal effective amount" denotes an amount of the composition or of the compounds of formula (I), which is sufficient for controlling harmful fungi on cultivated plants or in the protection of harvested or stored products or materials, not resulting in substantial damage to the treated plants, the treated stored products or harvest, or to the treated materials.

[0077] Examples of agrochemically acceptable auxiliaries include, but are not limited to, surfactants, carriers, solvents, dispersants, wetting agents, stickers, preservatives, and adjuvants.

[0078] The compounds of the present disclosure may be present either in pure form or as mixtures of different possible isomeric forms, such as stereoisomers or constitutional isomers. The various stereoisomers include enantiomers, diastereomers, chiral isomers, atropisomers, conformers, retainers, tautomers, optical isomers, and geometric isomers. Any desired mixtures of these isomers fall within the scope of the claims of the present disclosure. One skilled in the art will appreciate that one stereoisomer may be more active and / or may exhibit beneficial effects when enriched relative to the other isomer(s) or when separated from the other isomer(s). Additionally, the person skilled in the art knows processes or methods or technology to separate, enrich, and / or to selectively prepare said isomers.

[0079] The inventive compound of the present invention may, where appropriate, be present as mixtures of different possible isomeric forms, especially stereoisomers, such as E and Z isomers, threo and erythro isomers, as well as optical isomers. Where applicable, mixture of tautomers may also be present. Both the E and Z isomers, the threo and erythro isomers, the optical isomers, any desired mixtures thereof, and the possible tautomeric forms are hereby disclosed and claimed.

[0080] The embodiments herein and the various features and advantageous details thereof are explained in the non-limiting embodiments in the description. Descriptions of well-known components and processing techniques are omitted to not unnecessarily obscure the embodiments herein. The examples used herein are intended merely to facilitate an understanding of ways in which the embodiments herein may be practiced and to further enable those skilled in the art to practice the embodiments herein. Accordingly, the examples should not be construed as limiting the scope of the embodiments herein.

[0081] The description of the specific embodiments will so fully reveal the general nature of the embodiments herein that others can, by applying current knowledge, readily modify and / or adapt for various applications such specific embodiments without departing from the generic concept, and, therefore, such adaptations and modifications should and are intended to be comprehended within the meaning and range of equivalents of the disclosed embodiments. It is to be understood that the phraseology or terminology employed herein is for description and not of limitation. Therefore, while the embodiments herein have been described in terms of preferred embodiments, those skilled in the art will recognize that the embodiments herein can be practiced with modification within the spirit and scope of the embodiments as described herein.

[0082] Although the present invention will be described for particular embodiments, this description is not to be construed in a limiting sense.

[0083] In each case, the compounds of formula (I), according to the present invention, include their free form, hydrated forms, any polymorphs or salts thereof, e.g., in the form of an agriculturally usable product. Salts of the compounds of the formula (I) are agriculturally acceptable and applicable salts. They can be formed in a customary manner, e.g. by reacting the compound with an acid of the anion in question, in case the compounds of formula (I) have a basic functionality.

[0084] The salts may be formed with inorganic or organic acids and inorganic or organic bases. Examples of suitable acid addition salts include those formed with hydrochloric, hydrobromic, sulfuric, nitric, phosphoric, acetic, citric, lactic, oxalic, maleic, fumaric, succinic, benzoic, methanesulfonic, toluenesulfonic acid and salicylic acid.

[0085] Suitable base addition salts include salts formed with alkali metals (e.g., sodium, potassium), alkaline earth metals (e.g., calcium, magnesium), ammonium, and organic amines such as ethanolamine, diethanolamine, triethylamine, morpholine, lysine, arginine, piperidine and saccharin.

[0086] The term "N-oxide" includes any compounds of formula (I) which has at least one tertiary nitrogen atom that is oxidized to an N-oxide moiety.

[0087] The compounds of formula (I), (including all stereoisomers, tautomers, N-oxides, polymorphs and salts thereof), typically exist in more than one form, and formula (I) thus includes all crystalline and noncrystalline forms of the compounds that formula (I) represents. The term "polymorph" refers to a particular crystalline form of a chemical compound that can crystallize in different crystalline forms, these forms having different arrangements and / or conformations of the molecules in the crystal lattice. Although polymorphs can have the same chemical composition, they can also differ in composition due to the presence or absence of co-crystallized water or other molecules, which can be weakly or strongly bound in the lattice. Polymorphs can differ in such chemical, physical and biological properties as crystal shape, density, hardness, color, chemical stability, melting point, hygroscopicity, suspensibility, dissolution rate and biological availability. One skilled in the art will appreciate that a polymorph of a compound represented by formula (I) can exhibit beneficial effects (e.g., suitability for preparation of useful formulations, improved biological performance) relative to another polymorph or a mixture of polymorphs of the same compounds represented by formula (I). The preparation and isolation of a particular polymorph of the compounds represented by formula (I) can be achieved by methods known to those skilled in the art, including, for example, crystallization using selected solvents and temperatures.

[0088] The presence of one or more possible asymmetric carbon atoms in compounds of formula (I) means that the compound may occur in chiral isomeric forms, i.e., enantiomeric or diastereomeric. Also, atropisomers may occur as a result of restricted rotation about a single bond. Formula (I) is intended to include all those possible isomeric forms and mixtures thereof.

[0089] The present invention includes all those possible isomeric forms and mixtures thereof of the compounds of formula (I). Likewise, formula (I) is intended to include all possible tautomers (including lactamlactim tautomerism and keto-enol tautomerism) where present. The present invention includes all possible tautomeric forms for the compounds of formula (I).

[0090] Application of the compounds of the present disclosure or the compound of the present disclosure in a composition, optionally comprising other compatible compounds, to a plant or a plant material or locus thereof includes an application by a technique known to a person skilled in the art which includes but is not limited to spraying, coating, dipping, fumigating, impregnating, injecting and dusting.

[0091] The term “applied” means adhered to a plant or plant part either physically or chemically, including impregnation.

[0092] It has been found that the novel bicyclic acrylyl compounds of formula (I) have a very advantageous level of biological activity for protecting plants against diseases that are caused by phytopathogenic fungi.

[0093] In view of the above objectives, the present invention provides compounds of formula (I),

[0094]

[0095] wherein,

[0096] W is selected from NRWor O; wherein Rwis selected from hydrogen or Ci-Ce-alkyl;

[0097] R1is selected from the group consisting of hydrogen, halogen, C1-C3 -alkyl, C1-C3-haloalkyl and C3-C6-cycloalkyl;

[0098] R2is selected from the group consisting of hydrogen, halogen, methyl and methoxy;

[0099] R3is selected from the group consisting of hydrogen, halogen, Ci-C3-alkyl and Ci-C3-alkoxy;

[0100] R4is selected from the group consisting of hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-haloalkyl and C3-C6-cycloalkyl;

[0101] ring E represents a non-aromatic 5- or 6-membered carbocyclic or heterocyclic ring, fused to the phenyl ring D; wherein said non-aromatic 5- or 6-membered heterocyclic ring contains 1, 2 or 3 heteroatoms independently selected from N, NRd, O or S(0)o-2; said ring E is unsubstituted or substituted with one to six substituents independently selected from R5;

[0102] R5is selected from the group consisting of halogen, cyano, hydroxyl, Ci-Ce-alkyl, C2-C6 -alkenyl, C2-Ce-alkynyl, Ci-Ce-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, Cs-Ce-cycloalkyl, C3-C6-cycloalkyl-Ci-Ce-alkyl, Cs-Ce-cycloalkenyl, Cs-Ce-halocycloalkyl, Ci-Ce-alkoxy, C2-C6-alkenyloxy, C2-Ce-alkynyloxy, Ci-Ce-haloalkoxy, C2-C6-haloalkenyloxy, C2-C6-haloalkynyloxy, C3-C6-cycloalkyloxy, C’,-C(,-cycloalkyloxy-Ci-C(, -alk l. Cs-Ce-halocycloalkyloxy, Ci-Ce-alkylsulfanyl, Ci-Ce-alkylsulfinyl, Ci-Ce-alkylsulfonyl, Ci-Ce-haloalkylsulfanyl, Ci-Ce-haloalkylsulfinyl, Ci-Ce-haloalkylsulfonyl, oxo, thioxo, cyano-Ci-Ce-alkyl, -OC(O)-Ci-C6-alkyl, -OC(O)-Ci-C6-haloalkyl, -C(O)Ra, =N-C1-C6-alkyl, =N-Ci-C6-haloalkyl, -NRaRb, =N-ORCand =N-NH-RCX; or

[0103] two R5groups when attached to the same carbon atom, together with the carbon atom to which they are attached, may form a 3- to 6-membered non-aromatic carbocyclic or non-aromatic heterocyclic ring, wherein said heterocyclic ring contains 1, 2 or 3 heteroatoms independently selected from N, NRd, O or S(0)o-2;

[0104] Rais selected from the group consisting of hydrogen, halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy and Cs-Ce-cycloalkyl;

[0105] Rbis selected from the group consisting of hydrogen, halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy and Cs-Ce-cycloalkyl;

[0106] Rcis selected from the group consisting of hydrogen, halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy, Cs-Ce-cycloalkyl, C’,-C(,-cycloalk l-Ci-C(, -alk l. phenyl, phenyl-Ci-Ce -alkyl- and -C(O)RX; wherein said phenyl ring is unsubstituted or substituted with one to three substituents independently selected from halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy and Cs-Ce-cycloalkyl; Rcxis selected from the group consisting of hydrogen, halogen, Ci-Ce -alkyl, Ci-Ce-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C3-C6-cycloalkyl, -C(O)-Ci-C6-alkyl and -C(O)-Ci-C6- haloalkyl;

[0107] Rdis selected from the group consisting of hydrogen, halogen, C1-C8-alkyl, Ci-Ce-haloalkyl, Ci-Ce-alkoxy, Ci-Ce -haloalkoxy, C3-C6 -cycloalkyl, C’,-C(,-cycloalkyl-Ci-C(, -alkyl and -C(O)Ra; Rxis selected from the group consisting of hydrogen, halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy, Cs-Ce-cycloalkyl, C’,-C(,-cycloalkyl-Ci-C(, -alkyl and phenyl; wherein said phenyl ring is unsubstituted or substituted with one to three substituents independently selected from halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-Ce-alkoxy, Ci-Ce- haloalkoxy and C3-C6 -cycloalkyl; and

[0108] R6is selected from hydrogen or Ci-C3-alkyl;

[0109] or salts, stereoisomers, tautomers, polymorphs or N-oxides thereof.

[0110] In one embodiment of the present invention, the compounds of formula (I) are represented by the compounds of formula (IA) or salts, stereoisomers, tautomers, polymorphs or N-oxides thereof;

[0111]

[0112] wherein R1, R2, R3, R4, R5and R6are as defined for the compounds of formula (I) according to the present invention.

[0113] In another embodiment of the present invention, the compounds of formula (I) or (IA) are represented by the compounds of formula (IA- 1 ) or salts, stereoisomers, tautomers, polymorphs or N-oxides thereof, wherein R4is hydrogen and R1, R2, R3, R5and R6are as defined for the compounds of formula (I) according to the present invention.

[0114] In a preferred embodiment of the present invention, the compounds of formula (I) or (IA) or (IA-1) are represented by the compounds of formula (IA-2) or salts, stereoisomers, tautomers, polymorphs or N-oxides thereof, wherein R1is selected from hydrogen, halogen or Ci-C3-alkyl; R2, R3and R4are hydrogen; R6is methyl; and R5is as defined for the compounds of formula (I) according to the present invention. In another preferred embodiment of the present invention, the compounds of formula (I) or (IA) are represented by the compounds of formula (IA-2a) or salts, stereoisomers, tautomers, polymorphs or N-oxides thereof;

[0115]

[0116] wherein R1, R2, R3, R4and R5are as defined for the compounds of formula (I) according to the present invention.

[0117] In yet another preferred embodiment of the present invention, the compounds of formula (I) or (IA) are represented by the compounds of formula (IA-2b) or salts, stereoisomers, tautomers, polymorphs or N-oxides thereof;

[0118]

[0119] wherein R1, R2, R3, R4and R5are as defined for the compounds of formula (I) according to the present invention.

[0120] In one embodiment of the present invention, the compounds of formula (I) are represented by the compounds of formula (IB) or salts, stereoisomers, tautomers, polymorphs or N-oxides thereof;

[0121]

[0122] wherein R1, R2, R3, R4, R5, Rwand R6are as defined for the compounds of formula (I) according to the present invention. In another embodiment of the present invention, the compounds of formula (I) or (IB) are represented by the compounds of formula (IB-1) or salts, stereoisomers, tautomers, polymorphs or N-oxides thereof; wherein Rwand R4are hydrogen, and R1, R2, R3, R5and R6are as defined for the compounds of formula (I) according to the present invention.

[0123] In a preferred embodiment of the present invention, the compounds of formula (I) or (IB) or (IB-1) are represented by the compounds of formula (IB-2) or salts, stereoisomers, tautomers, polymorphs or N-oxides thereof; wherein R1is selected from chloro, fluoro, methyl or ethyl; Rw, R2, R3and R4are hydrogen; R6is methyl and R5is as defined for the compounds of formula (I) according to the present invention.

[0124] The following list provides definitions, including preferred definitions, for the substituents R1, R2, R3, R4, R5, R6, W, Rw, Ra, Rb, Rc, Rcx, Rd, Rxand ring E with reference to the compounds of formula (I) of the present invention. For any one of these substituents, any of the definitions given below may be combined with any definition of any other substituent given below or elsewhere in this document. In one embodiment of the present invention, W is selected from NRWor oxygen (O).

[0125] In another embodiment of the present invention, W is NRW, wherein Rwis selected from hydrogen or Ci-C3-alkyl.

[0126] In yet another embodiment of the present invention, W is NRW, wherein Rwis hydrogen.

[0127] In a preferred embodiment of the present invention, W is oxygen (O).

[0128] In one embodiment of the present invention, R1is selected from the group consisting of hydrogen, halogen, Ci-C3-alkyl, Ci-C3-haloalkyl and C3-C6-cycloalkyl.

[0129] In another embodiment of the present invention, R1is selected from the group consisting of hydrogen, halogen and Ci-C3-alkyl.

[0130] In yet another embodiment of the present invention, R1is selected from the group consisting of hydrogen, halogen, methyl, ethyl and propyl.

[0131] In a preferred embodiment of the present invention, R1is selected from the group consisting of hydrogen, fluoro, chloro, methyl, ethyl and propyl.

[0132] In another preferred embodiment of the present invention, R1is selected from the group consisting of hydrogen, fluoro, chloro, methyl and ethyl.

[0133] In yet another preferred embodiment of the present invention, R1is selected from the group consisting of hydrogen, fluoro, chloro and methyl.

[0134] In a more preferred embodiment of the present invention, R1is methyl. In one embodiment of the present invention, R2is selected from the group consisting of hydrogen, halogen, methyl and methoxy.

[0135] In another embodiment of the present invention, R2is selected from the group consisting of hydrogen, halogen and methyl.

[0136] In a preferred embodiment of the present invention, R2is selected from hydrogen, fluoro, chloro or methyl.

[0137] In a more preferred embodiment of the present invention, R2is hydrogen.

[0138] In one embodiment of the present invention, R3is selected from the group consisting of hydrogen, halogen, C1-C3-alkyl and C1-C3-alkoxy.

[0139] In a preferred embodiment of the present invention, R3is selected from the group consisting of hydrogen, halogen and C1-C8-alkyl.

[0140] In a more preferred embodiment of the present invention, R3is hydrogen.

[0141] In one embodiment of the present invention, R4is selected from the group consisting of hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-haloalkyl and C3-C6-cycloalkyl.

[0142] In another embodiment of the present invention, R4is selected from the group consisting of hydrogen, halogen, cyano, C1-C3-alkyl, C1-C3-alkoxy, C1-C3-haloalkyl and C3-C6-cycloalkyl.

[0143] In a preferred embodiment of the present invention, R4is selected from the group consisting of hydrogen, halogen, cyano and C1-C3 -alkyl.

[0144] In another preferred embodiment of the present invention, R4is selected from the group consisting of hydrogen, fluoro, cyano and methyl.

[0145] In a more preferred embodiment of the present invention, R4is hydrogen.

[0146] In one embodiment of the present invention, ring E represents a non-aromatic 5- or 6-membered carbocyclic or heterocyclic ring, fused to the phenyl ring D; wherein said non-aromatic 5- or 6-membered heterocyclic ring contains 1, 2 or 3 heteroatoms independently selected from N, NRd, O or S(O)0-2; said ring E is unsubstituted or substituted with one to six substituents independently selected from R5.

[0147] In another embodiment of the present invention, ring E represents a non-aromatic 5- or 6-membered carbocyclic or heterocyclic ring, fused to the phenyl ring D; wherein said non-aromatic 5- or 6-membered heterocyclic ring contains 1, 2 or 3 heteroatoms independently selected from N, NRd, O or S(O)0-2; said ring E is unsubstituted or substituted with one to four substituents independently selected from R5. In yet another embodiment of the present invention, ring E represents a non-aromatic 5- or 6-membered carbocyclic or heterocyclic ring, fused to the phenyl ring D; wherein said non-aromatic 5- or 6-membered heterocyclic ring contains 1 or 2 heteroatoms independently selected from N, NRd, O or S; said ring E is unsubstituted or substituted with one to four substituents independently selected from R5. In yet another embodiment of the present invention, ring E represents a non-aromatic 5- or 6-membered carbocyclic or heterocyclic ring, fused to the phenyl ring D; wherein said non-aromatic 5- or 6-membered heterocyclic ring contains 1 or 2 heteroatoms independently selected from N, NRdor O; said ring E is unsubstituted or substituted with one to four substituents independently selected from R5. In yet another embodiment of the present invention, ring E represents a non-aromatic 5- or 6-membered carbocyclic ring, fused to the phenyl ring D; said ring E is unsubstituted or substituted with one to five substituents independently selected from R5.

[0148] In yet another embodiment of the present invention, ring E represents a non-aromatic 5- or 6-membered carbocyclic ring, fused to the phenyl ring D; said ring E is unsubstituted or substituted with one to four substituents independently selected from R5.

[0149] In yet another embodiment of the present invention, ring E represents a non- aromatic 5- or 6-membered heterocyclic ring fused to the phenyl ring D; wherein said non-aromatic 5- or 6-membered heterocyclic ring contains 1, 2 or 3 heteroatoms independently selected from N, NRd, O or S(0)o-2; said ring E is unsubstituted or substituted with one to five substituents independently selected from R5.

[0150] In yet another embodiment of the present invention, ring E represents a non- aromatic 5- or 6-membered heterocyclic ring fused to the phenyl ring D; wherein said non-aromatic 5- or 6-membered heterocyclic ring contains 1, 2 or 3 heteroatoms independently selected from N, NRd, O or S(0)o-2; said ring E is unsubstituted or substituted with one to four substituents independently selected from R5.

[0151] In yet another embodiment of the present invention, ring E represents a non- aromatic 5- or 6-membered heterocyclic ring fused to the phenyl ring D; wherein said non-aromatic 5- or 6-membered heterocyclic ring contains 1 or 2 heteroatoms independently selected from N, NRd, O or S; said ring E is unsubstituted or substituted with one to four substituents independently selected from R5.

[0152] In yet another embodiment of the present invention, ring E represents a non-aromatic 5- or 6-membered heterocyclic ring fused to the phenyl ring D; wherein said non-aromatic 5- or 6-membered heterocyclic ring contains 1 or 2 heteroatoms independently selected from N, NRd, or O; said ring E is unsubstituted or substituted with one to four substituents independently selected from R5.

[0153] In one embodiment of the present invention, the fragment

[0154]

[0155] is represented by but not limited to, DE-1 to DE-20, as shown in Table A: Table A

[0156]

[0157] R4, Rdand R5are as defined for the compounds of formula (I) according to the present invention.

[0158] In a preferred embodiment of the present invention, the fragment

[0159]

[0160] is represented as shown below in Table B:

[0161]

[0162]

[0163]

[0164]

[0165] wherein indicates the point of attachment to the phenyl ring containing the acrylyl group and R4, Rdand R5are as defined for the compounds of formula (I) according to the present invention.

[0166] In one embodiment of the present invention, R5is selected from the group consisting of halogen, cyano, hydroxyl, Ci-Ce-alkyl, C2-Ce-alkenyl, C2-Ce-alkynyl, Ci-Ce-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, Cs-Ce-cycloalkyl, C’,-C(,-cycloalkyl-C’i-C(, -alkyl. Cs-Ce-cycloalkenyl, C3-C6-halocycloalkyl, Ci-Ce-alkoxy, C2-C6-alkenyloxy, C2-Ce-alkynyloxy, Ci-Ce-haloalkoxy, C2-C6-haloalkenyloxy, C2-C6-haloalkynyloxy, C3-C6 -cycloalkyloxy, C’,-C(,-cycloalkyloxy-Ci-C(, -alkyl. C3-C6-halocycloalkyloxy, Ci-Ce-alkylsulfanyl, Ci-Ce-alkylsulfmyl, Ci-Ce-alkylsulfonyl, Ci-Ce-haloalkylsulfanyl, Ci-Ce-haloalkylsulfinyl, Ci-Ce-haloalkylsulfonyl, oxo, thioxo, cyano-Ci-Ce-alkyl, -OC(O)-Ci-C6-alkyl, -OC(O)-Ci-C6-haloalkyl, -C(O)Ra, =N-Ci-C6-alkyl, =N-Ci-C6-haloalkyl, -NRaRb, =N-ORCand =N-NH-RCX

[0167] In another embodiment of the present invention, R5is selected from the group consisting of halogen, cyano, hydroxyl, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Cs-Ce-cycloalkyl, Cs-Ce-halocycloalkyl, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy, Cs-Ce-cycloalkyloxy, C’.-Ce-cycloalkyloxy-Ci-C’, -alkyl, Ci-Ce-alkylsulfanyl, Ci-Ce-alkylsulfmyl, Ci-Ce-alkylsulfonyl, Ci-Ce-haloalkylsulfanyl, Ci-Ce-haloalkylsulfinyl, Ci-Ce-haloalkylsulfonyl, oxo, thioxo, cyano-Ci-Ce-alkyl, -OC(O)-Ci-C6-alkyl, -OC(O)-Ci-C6-haloalkyl, -C(O)Ra, =N-Ci-C6-alkyl, =N-Ci-C6-haloalkyl, -NRaRb, =N-ORCand =N-NH-RCX

[0168] In a preferred embodiment of the present invention, R5is selected from the group consisting of halogen, cyano, hydroxyl, Ci-C4-alkyl, Ci-C4-haloalkyl, Cs-Ce-cycloalkyl, Cs-Ce-halocycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Cs-Ce-cycloalkyloxy, Ci-C4-alkylsulfanyl, Ci-C4-alkylsulfinyl, Ci-C4-alkylsulfonyl, Ci-C4-haloalkylsulfanyl, Ci-C4-haloalkylsulfmyl, Ci-C4-haloalkylsulfonyl, oxo, thioxo, cyano-Ci-Ci-alkyl, -OC(O)-Ci-C6-alkyl, -OC(O)-Ci-C6-haloalkyl, -C(O)Ra, =N-Ci-C6-alkyl, =N-Ci-C6-haloalkyl, -NRaRb, =N-ORCand =N-NH-RCX

[0169] In another preferred embodiment of the present invention, R5is selected from the group consisting of halogen, hydroxyl, Ci-C4-alkyl, Ci-C4-haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C1-C4-alkoxy, Ci-C4-haloalkoxy, oxo, thioxo, -OC(O)-Ci-C3-alkyl, -OC(O)-Ci-C3-haloalkyl, =N-Ci-C3-alkyl, =N-Ci-C3-haloalkyl, =N-ORCand =N-NH-RCX

[0170] In yet another preferred embodiment of the present invention, R5is selected from the group consisting of halogen, hydroxyl, Ci-C4-alkyl, Ci-C4-haloalkyl, oxo, thioxo, -OC(O)-Ci-C3-alkyl, -OC(O)-Ci-C3-haloalkyl, =N-Ci-C3-alkyl, =N-ORCand =N-NH-RCX. In yet another preferred embodiment of the present invention, R5is selected from the group consisting of halogen, hydroxyl, Ci-C4-alkyl, oxo, -OC(O)-Ci-C3-alkyl, =N-Ci-C3-alkyl, =N-ORCand =N-NH-RCX. In yet another preferred embodiment of the present invention, (R5)o-6 includes ranges selected from (R5)O-1, (R5)O-2, (R5)O-3, (R5)O-4, (R5)O-5 or (R5)O.6.

[0171] In one embodiment of the present invention, two R5groups when attached to the same carbon atom, together with the carbon atom to which they are attached, may form a 3- to 6-membered non-aromatic carbocyclic or non-aromatic heterocyclic ring, wherein said heterocyclic ring contains 1, 2 or 3 heteroatoms independently selected from N, NRd, O or S(0)o-2.

[0172] In another embodiment of the present invention, two R5groups when attached to the same carbon atom, together with the carbon atom to which they are attached, may form a 3- to 6-membered non-aromatic carbocyclic or non-aromatic heterocyclic ring, wherein said heterocyclic ring contains 1 or 2 heteroatoms independently selected from N, NRd, O or S.

[0173] In yet another embodiment of the present invention, two R5groups when attached to the same carbon atom, together with the carbon atom to which they are attached, may form a 3- to 5 -membered non-aromatic carbocyclic ring.

[0174] In yet another embodiment of the present invention, two R5groups when attached to the same carbon atom, together with the carbon atom to which they are attached, may form a 3- to 4-membered non-aromatic carbocyclic ring.

[0175] In yet another embodiment of the present invention, two R5groups when attached to the same carbon atom, together with the carbon atom to which they are attached, may form a 3 -membered non-aromatic carbocyclic ring.

[0176] In yet another embodiment of the present invention, two R5groups when attached to the same carbon atom, together with the carbon atom to which they are attached, may form a 3- to 5 -membered non-aromatic heterocyclic ring, wherein said heterocyclic ring contains 1 or 2 heteroatoms independently selected from N, NRd, O or S.

[0177] In yet another embodiment of the present invention, two R5groups when attached to the same carbon atom, together with the carbon atom to which they are attached, may form a 3- to 4-membered non-aromatic heterocyclic ring, wherein said heterocyclic ring contains 1 or 2 heteroatoms independently selected from N, NRd, O or S.

[0178] In yet another embodiment, the term “may form” as used herein indicates that the two R5groups attached to the same carbon atom can optionally combine, together with the carbon atom, to form a non-aromatic carbocyclic or non-aromatic heterocyclic ring. That is, ring formation is not mandatory, and the R5groups may alternatively remain as separate substituents on the carbon atom. In one embodiment of the present invention, Rais selected from the group consisting of hydrogen, halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy and Cs-Ce-cycloalkyl.

[0179] In another embodiment of the present invention, Rais selected from the group consisting of hydrogen, halogen, Ci-C-ralkyl, C1-C4 -alkoxy and Cs-Ce-cycloalkyl.

[0180] In yet another embodiment of the present invention, Rais selected from the group consisting of hydrogen, halogen, Ci-C-ralkyl, C1-C3 -alkoxy and Cs-Cs-cycloalkyl.

[0181] In yet another embodiment of the present invention, Rais selected from the group consisting of hydrogen, halogen and Ci-C-ralkyl.

[0182] In a preferred embodiment of the present invention, Rais Ci-C4-alkyl.

[0183] In one embodiment of the present invention, Rbis selected from the group consisting of hydrogen, halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy and Cs-Ce-cycloalkyl.

[0184] In another embodiment of the present invention, Rbis selected from the group consisting of hydrogen, halogen, Ci-C4-alkyl, C1-C4 -alkoxy and Cs-Ce-cycloalkyl.

[0185] In yet another embodiment of the present invention, Rbis selected from the group consisting of hydrogen, halogen, C1-C8-alkyl, C1-C3 -alkoxy and Cs-Cs-cycloalkyl.

[0186] In yet another embodiment of the present invention, Rbis selected from the group consisting of hydrogen, halogen, Ci-C3-alkyl and Ci-C3-alkoxy.

[0187] In yet another embodiment of the present invention, Rbis selected from hydrogen or Ci-C3-alkyl. In one embodiment of the present invention, Rcis selected from the group consisting of hydrogen, halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Cs-Ce-cycloalkyl, C’,-C(,-cycloalk l-C’i-C(, -alk l. phenyl, phenyl-Ci-Ce-alkyl- and -C(O)RX; wherein said phenyl ring is unsubstituted or substituted with one to three substituents independently selected from halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-Ce-alkoxy, Ci-Ce -haloalkoxy and C3-C6 -cycloalkyl.

[0188] In another embodiment of the present invention, Rcis selected from the group consisting of hydrogen, halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, G-G, -cycloalkyl. C’,-C(,-cycloalk l-C’i-C(, -alk l. phenyl, phenyl-Ci-C3-alkyl- and -C(O)RX; wherein said phenyl ring is unsubstituted or substituted with one to three substituents independently selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and C3-C5 -cycloalkyl.

[0189] In yet another embodiment of the present invention, Rcis selected from the group consisting of hydrogen, Ci-C4-alkyl, G-G-cycloalkyl. G-G-cycloalkyl-G-G-alkyl, phenyl, phenyl-Ci-C3-alkyl and -C(O)RX; wherein said phenyl ring is unsubstituted or substituted with one to two substituents independently selected from halogen, Ci-C3-alkyl, Ci-C3-haloalkyl, Ci-C3-alkoxy and C1-C3-haloalkoxy. In a preferred embodiment of the present invention, Rcis selected from the group consisting of hydrogen, Ci-C4-alkyl, Cs-Ce-cycloalkyl, Cs-Cs-cycloalkyl-Ci-Cs -alkyl, phenyl, phcnyl-Ci-C\ -alkyl and -C(O)RXwherein said phenyl ring is unsubstituted or substituted with one substituent selected from halogen, C1-C8-alkyl, C1-C3-haloalkyl. C 1-C3 -alkoxy and C 1-C3 -haloalkoxy.

[0190] In another preferred embodiment of the present invention, Rcis selected from the group consisting of hydrogen, Ci-C4-alkyl, O-C’s-cycloalkyl. Cs-Cs-cycloalkyl-C1-C8-alkyl, phenyl, phenyl-Ci-C3-alkyl and -C(O)RXwherein said phenyl ring is unsubstituted or substituted with one substituent selected from halogen, Ci-C3-alkyl and Ci-C3-alkoxy.

[0191] In yet another preferred embodiment of the present invention, Rcis selected from the group consisting of hydrogen, Ci-C4-alkyl, Cs-Cs-cycloalkyl-C1-C8-alkyl, phenyl-Ci-C3-alkyl and -C(O)RXwherein said phenyl ring is unsubstituted or substituted with a Ci-C3-alkyl group.

[0192] In yet another preferred embodiment of the present invention, Rcis selected from the group consisting of hydrogen, Ci-C4-alkyl, C3-C4-cycloalkyl-Ci-C3-alkyl, phenyl-Ci-C2-alkyl and -C(O)RXwherein said phenyl ring is unsubstituted or substituted with a methyl group.

[0193] In yet another preferred embodiment of the present invention, Rcis selected from the group consisting of hydrogen, Ci-C4-alkyl, C3-C4-cycloalkyl-Ci-C2-alkyl, phenyl-Ci-C2-alkyl and -C(O)RXwherein said phenyl ring is unsubstituted or substituted with a methyl group.

[0194] In one embodiment of the present invention, Rcxis selected from the group consisting of hydrogen, halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy,

[0195]

[0196] -cycloalkyl. -C(O)-Ci-C6-alkyl and -C(O)-Ci-C6-haloalkyl.

[0197] In another embodiment of the present invention, Rcxis selected from the group consisting of hydrogen, halogen, Ci-C3-alkyl, Ci-C3-haloalkyl, Ci-C3-alkoxy, Ci-C3-haloalkoxy,

[0198]

[0199] -cycloalkyl. -C(O)-Ci-C3-alkyl and -C(O)-Ci-C3-haloalkyl.

[0200] In yet another embodiment of the present invention, Rcxis selected from the group consisting of hydrogen, Ci-C3-alkyl, Ci-C3-alkoxy, -C(O)-Ci-C3-alkyl and -C(O)-Ci-C3-haloalkyl.

[0201] In a preferred embodiment of the present invention, Rcxis selected from -C(O)-Ci-C3-alkyl or -C(O)-Ci-C3-haloalkyl.

[0202] In another preferred embodiment of the present invention, Rcxis -C(O)-Ci-C3-alkyl.

[0203] In one embodiment of the present invention, Rdis selected from the group consisting of hydrogen, halogen, C1-C8-alkyl, Ci-Ce-haloalkyl, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy, C\-G, -cycloalkyl. C3-C6-cycloalkyl-Ci-Ce-alkyl and -C(O)Ra. In another embodiment of the present invention, Rdis selected from the group consisting of hydrogen, halogen, Ci-Ce-alkyl, Ci-Ohaloalk l. Ci-C4-alkoxy, Ci-C4-haloalkoxy, Cs-Ce-cycloalkyl, C3-Ce-cycloalkyl-Ci-C4-alkyl and -C(O)Ra.

[0204] In yet another embodiment of the present invention, Rdis selected from the group consisting of hydrogen, halogen, Ci-Ce-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Cs-Ce-cycloalkyl, C3-C6-cycloalkyl-Ci-C3-alkyl and -C(O)Ra.

[0205] In a preferred embodiment of the present invention, Rdis selected from the group consisting of hydrogen, halogen, Ci-Ce-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C2-alkyl and -C(O)Ra.

[0206] In another preferred embodiment of the present invention, Rdis selected from the group consisting of hydrogen, Ci-Ce-alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl-Ci-C2-alkyl and -C(O)Ra.

[0207] In one embodiment of the present invention, Rxis selected from the group consisting of hydrogen, halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy, C3-C6-cycloalkyl, C3-Ce-cycloalkyl-Ci-Ce-alkyl and phenyl; wherein said phenyl ring is unsubstituted or substituted with one to three substituents independently selected from halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-Ce-alkoxy, Ci-Ce -haloalkoxy and C3-Ce -cycloalkyl.

[0208] In another embodiment of the present invention, Rxis selected from the group consisting of hydrogen, halogen, Ci-Ce-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C3-alkyl and phenyl; wherein said phenyl ring is unsubstituted or substituted with one to two substituents independently selected from halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy and C3-Ce -cycloalkyl.

[0209] In a preferred embodiment of the present invention, Rxis selected from the group consisting of Ci-Ce-alkyl, C3-Ce -cycloalkyl and C3-C6-cycloalkyl-Ci-C2-alkyl.

[0210] In another preferred embodiment of the present invention, Rxis selected from the group consisting of C1-C8-alkyl, C3-Ce -cycloalkyl and C3-C6-cycloalkyl-Ci-C2-alkyl.

[0211] In another preferred embodiment of the present invention, Rxis selected from the group consisting of Ci-C4-alkyl, C3-Ce -cycloalkyl and C3-C6-cycloalkyl-Ci-C2-alkyl.

[0212] In one embodiment of the present invention, R6is selected from hydrogen or Ci-C3-alkyl.

[0213] In another embodiment of the present invention, R6is Ci-C3-alkyl.

[0214] In a preferred embodiment of the present invention, R6is selected from methyl, ethyl, n-propyl or isopropyl.

[0215] In a more preferred embodiment of the present invention, R6is methyl. In one embodiment of the present invention, one or more carbon atoms of ring E are unsubstituted or substituted with one to six substituents independently selected from R5.

[0216] In another embodiment of the present invention, when two R5substituents are present on ring E, they may be located on the same carbon atom or on different carbon atoms of ring E.

[0217] For the substituents defined herein above, any or more of the definitions provided above may be combined with any definition of any other substituent defined herein above. Such combinations include all variations within the scope of the definitions provided. For example, but not limited to, the present invention provides compounds of formula (I) or salts, stereoisomers, tautomers, polymorphs or N-oxides thereof, wherein

[0218] W is selected from NRWor O; wherein Rwis hydrogen;

[0219] R1is selected from the group consisting of hydrogen, halogen and C1-C3 -alkyl;

[0220] R2and R3are hydrogen;

[0221] R4is selected from the group consisting of hydrogen, halogen, cyano and C1-C3 -alkyl;

[0222] ring E represents a non-aromatic 5- or 6-membered carbocyclic or heterocyclic ring, fused to the phenyl ring D; wherein said non-aromatic 5- or 6-membered heterocyclic ring contains 1 or 2 heteroatoms independently selected from N, NRd, O or S; said ring E is unsubstituted or substituted with one to four substituents independently selected from R5;

[0223] R5is selected from the group consisting of halogen, cyano, hydroxyl, Ci-C-ralkyl, Ci-C4-haloalkyl, C3-Ce-cycloalkyl, O-Ce-halocycloalkyl. Ci-C -alkoxy. Ci-C4-haloalkoxy, G-Ce-cycloalkyloxy. C1-C4-alkylsulfanyl, Ci-C4-alkylsulfmyl, Ci-C4-alkylsulfonyl, Ci-C4-haloalkylsulfanyl, C1-C4-haloalkylsulfinyl, Ci-C4-haloalkylsulfonyl, oxo, thioxo, cyano-Ci-C4-alkyl, -OC(O)-Ci-C6-alkyl, -OC(O)-Ci-C6-haloalkyl, -C(O)Ra, =N-Ci-C6-alkyl, =N-Ci-C6-haloalkyl, -NRaRb, =N-ORCand =N-NH-Rcx; or

[0224] two R5groups when attached to the same carbon atom, together with the carbon atom to which they are attached, may form a 3 - to 5 -membered non-aromatic carbocyclic ring;

[0225] Rais selected from the group consisting of hydrogen, halogen and Ci-C4-alkyl;

[0226] Rbis selected from the group consisting of hydrogen, halogen, Ci-C3-alkyl, and Ci-C3-alkoxy; Rcis selected from the group consisting of hydrogen, Ci-C4-alkyl, G-G, -cycloalkyl. C3-C5- cycloalkyl-Ci-C3-alkyl, phenyl, phenyl-Ci-C3-alkyl and -C(O)RXwherein said phenyl ring is unsubstituted or substituted with one substituent selected from halogen, Ci-C3-alkyl, C1-C3- haloalkyl, Ci-C3-alkoxy and Ci-C3-haloalkoxy;

[0227] Rcxis selected from the group consisting of hydrogen, Ci-C3-alkyl, Ci-C3-alkoxy, -C(O)-Ci-C3- alkyl and -C(O)-Ci-C3-haloalkyl; Rdis selected from the group consisting of hydrogen, halogen, Ci-Ce -alkyl, Ci-C4-haloalkyl, Ci- C4-alkoxy, Ci-C4-haloalkoxy, Cs-Ce-cycloalkyl, Cs-Ce-cycloalkyl-Ci-Cs -alkyl and -C(O)Ra; Rxis selected from the group consisting of Ci-Ce-alkyl, C3-C6 -cycloalkyl and Cs-Ce-cycloalkyl-Ci- C2-alkyl; and

[0228] R6is Ci-C3-alkyl.

[0229] In yet another embodiment, the present invention provides compounds of formula (I) or salts, stereoisomers, tautomers, polymorphs or N-oxides thereof, wherein

[0230] W is selected from NRWor O; wherein Rwis hydrogen;

[0231] R1is selected from the group consisting of hydrogen, halogen and C1-C3 -alkyl;

[0232] R2and R3are hydrogen;

[0233] R4is selected from the group consisting of hydrogen, halogen, cyano and C1-C3 -alkyl;

[0234]

[0235] is represented as defined in Table B; wherein indicates the point of attachment to the phenyl ring containing the acrylyl group;

[0236] R5is selected from the group consisting of halogen, cyano, hydroxyl, Ci-C4-alkyl, Ci-C4-haloalkyl, C3-Ce-cycloalkyl, Cs-Ce-halocycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Cs-Ce-cycloalkyloxy, C1-C4-alkylsulfanyl, Ci-C4-alkylsulfmyl, Ci-C4-alkylsulfonyl, Ci-C4-haloalkylsulfanyl, C1-C4-haloalkylsulfinyl, Ci-C4-haloalkylsulfonyl, oxo, thioxo, cyano-Ci-C4-alkyl, -OC(O)-Ci-C6-alkyl, -OC(O)-Ci-C6-haloalkyl, -C(O)Ra, =N-Ci-C6-alkyl, =N-Ci-C6-haloalkyl, -NRaRb, =N-ORCand =N-NH-Rcx; or

[0237] two R5groups when attached to the same carbon atom, together with the carbon atom to which they are attached, may form a 3 - to 5 -membered non-aromatic carbocyclic ring;

[0238] Rais selected from the group consisting of hydrogen, halogen and Ci-C4-alkyl;

[0239] Rbis selected from the group consisting of hydrogen, halogen, C1-C3 -alkyl, and C1-C3 -alkoxy; Rcis selected from the group consisting of hydrogen, Ci-C4-alkyl, Cs-Ce-cycloalkyl, C3-C5- cycloalkyl-C1-C8-alkyl, phenyl, phcnyl-Ci-C\ -alkyl and -C(O)RXwherein said phenyl ring is unsubstituted or substituted with one substituent selected from halogen, C1-C3 -alkyl, C1-C3- haloalkyl, C 1-C3 -alkoxy and C1-C3 -haloalkoxy;

[0240] Rcxis selected from the group consisting of hydrogen, C1-C3 -alkyl, C1-C3 -alkoxy, -C(O)-Ci-C3- alkyl and -C(O)-Ci-C3-haloalkyl; Rdis selected from the group consisting of hydrogen, halogen, Ci-Ce -alkyl, Ci-C4-haloalkyl, Ci- C4-alkoxy, Ci-C4-haloalkoxy, Cs-Ce-cycloalkyl, C’.-Ce-cycloalkyl-Ci-C’, -alkyl and -C(O)Ra; Rxis selected from the group consisting of Ci-Ce-alkyl, C3-C6 -cycloalkyl and Cs-Ce-cycloalkyl-Ci- C2-alkyl; and

[0241] R6is Ci-C3-alkyl.

[0242] In yet another embodiment, the present invention provides a method for preparing the compounds of formula (I) or salts, stereoisomers, tautomers, polymorphs or N-oxides thereof.

[0243] In yet another embodiment, the compounds of formula (I) may exist as a mixture of E and Z isomers. In yet another embodiment, the compounds of formula (I) are E isomers.

[0244] In yet another embodiment, the compounds of formula (I) are Z isomers.

[0245] In one embodiment, the present invention provides a process for preparing the compounds of formula (IA) or salts, stereoisomers or tautomers thereof, which comprises the step of:

[0246] reacting a compound of formula (IV) with a compound of formula (II-A) or (II-B), in the presence of a suitable palladium catalyst and a suitable base to obtain the compounds of formula (IA);

[0247]

[0248] wherein R1, R2, R3, R4, R5and R6are as defined above.

[0249] Alternatively, in another embodiment, the present invention provides a process for preparing the compounds of formula (IA) or salts, stereoisomers or tautomers thereof, which comprises the step of:

[0250] reacting a compound of formula (III) with a compound of formula (III-A), in the presence of a suitable palladium catalyst and a suitable base to obtain the compounds of formula (IA);

[0251]

[0252] wherein R1, R2, R3, R4, R5and R6are as defined above.

[0253] In yet another embodiment, the present invention provides a process for preparing the compounds of formula (IB) or salts, stereoisomers or tautomers thereof, which comprises the step of:

[0254] reacting a compound of formula (IA) with a suitable amine of formula (Vlll-a), to obtain the compounds of formula (IA);

[0255]

[0256] wherein R1, R2, R3, R4, R5, R6and Rware as defined above.

[0257] The compounds of the present invention as defined by formula (I) and / or in Table 1 may be prepared, in a known manner, in a variety of ways as described in the schemes. Compounds of the present invention can be made as shown in the following schemes, in which, unless otherwise stated, the definition of each variable is as defined above for the compounds of formula (I).

[0258] General Synthetic Schemes

[0259] Scheme 1

[0260]

[0261] The compounds of formula (IA) can be synthesized under Suzuki coupling conditions by reacting compounds of formula (IV) with either a boronic acid of formula (II-A) or a boronate ester of formula (II-B). The reaction is typically performed in the presence of a palladium catalyst, such as dichlorofl, 1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (Pd(dppf)C12-CH2C12), although other palladium(O) or palladium(II) complexes such as Pd(PPh3)4 or Pd(PPh3)2C12 may also be used. Suitable bases include, but are not limited to, sodium carbonate (Na₂CO₃), potassium carbonate (K2CO3) or caesium carbonate (Cs₂CO₃). The reaction can be carried out at a temperature ranging from 80 to 100 °C. The transformation is preferably carried out in the presence of a suitable solvent, such as 1,4-dioxane-water or DME-water. Such transformation is reported in the literature, for example, see: Chem. Soc. Rev., 2014, 43, 412. Compounds of formula (II -A) and (II-B) are commercially available or may be prepared from compounds of formula (III-A) by using standard borylation reaction conditions, such as those involving a palladium catalyst, bis(pinacolato)diboron, a suitable base, in an appropriate solvent.

[0262] Scheme 2

[0263]

[0264] Alternatively, compounds of formula (IA) can also be synthesized under Suzuki coupling conditions by reacting compounds of formula (III) with compounds of formula (III-A). The reaction is typically performed in the presence of a palladium catalyst, such as dichloro[1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (Pd(dppf)Cl₂·CH₂Cl₂), although other palladium(O) or palladium(II) complexes such as Pd(PPh3)4 or Pd(PPh3)2C12 may also be used. Suitable bases include, but are not limited to, sodium carbonate (Na₂CO₃), potassium carbonate (K2CO3) or caesium carbonate (Cs₂CO₃). The reaction can be carried out at a temperature ranging from 60 to 100 °C. The transformation is preferably carried out in the presence of a suitable solvent, such as 1,4-dioxane-water or dimethoxyethane(DME)-water. The compounds of formula (III-A) with the required substitution pattern can either be purchased from commercial sources or can be prepared using literature-known procedures.

[0265] Scheme 3

[0266]

[0267] Compounds of formula (III) can be prepared from compounds of formula (IV) by reacting them with bis(pinacolato) diboron of formula (IV-A). The reaction is typically performed in the presence of a palladium catalyst, such as dichloro[1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (Pd(dppf)Cl₂·CH₂Cl₂), although other palladium(O) or palladium(II) complexes such as Pd(PPh3)4 or Pd(PPh3)2C12 may also be used. Suitable bases include, but are not limited to, potassium phosphate or potassium acetate. The reaction can be carried out at a temperature ranging from 90 to 120 °C. The transformation is preferably carried out in the presence of a suitable solvent such as 1,4-dioxane, toluene or 1,2-dimethoxyethane (DME).

[0268] Scheme 4

[0269]

[0270] Compounds of formula (IV) can be obtained from compounds of formula (V) by treatment with a suitable base, such as sodium methoxide or sodium hydride, and a formylating agent, such as methyl formate, to generate compounds of formula (V-A), followed by methylation with a reagent, such as dimethyl sulfate, in the presence of a suitable base, such as potassium carbonate. Alternatively, compounds of formula (IV) can also be obtained directly from compounds of formula (V) via treatment with an orthoester, such as trimethyl orthoformate (HC(OMe)3), optionally in the presence of an acid, such as sulphuric acid or hydrochloric acid, in a suitable solvent such as methanol, as shown in Scheme 4. Such transformations are known in the literature, for examples, see: J. Agric. Food Chem. 2007, 55, 5697-5700, Molecules 2010, 15, 9024-9034 and Org. Process Res. Dev. 2015, 19, 639-645.

[0271] Scheme 5

[0272]

[0273] Compounds of formula (V) can be obtained from compounds of formula (VI) by treatment with an organic or inorganic base and compounds of formula (VII), in organic solvents such as N, N-dimethylformamide or N-methylpyrrolidone, as shown in Scheme 5. Such transformations are known in the literature, for example, see: Eur. J. Org. Chem., 2015, 2197-2204. Compounds of formula (VII) are commercially available or can be readily prepared from commercially available compounds by standard functional group transformations.

[0274] Scheme 6

[0275]

[0276] Compounds of formula (IB-1) can be obtained from compounds of formula (IA) by reacting them with an amine of formula (VIII), in the presence of a suitable solvent such as water, tetrahydrofuran or 1,4-dioxane, at a temperature ranging from 0 to 25 °C, as shown in Scheme 6. Such transformations are known in the literature, for example, see: Nat. Commun. 2021, 12, 5964.

[0277] In one embodiment, compounds of formula (I) of the present invention may possess a number of benefits including, inter alia, advantageous levels of biological activity for protecting plants against phytopathogenic fungi or superior properties for use as an agrochemical active ingredient (for example, greater biological activity, an advantageous spectrum of activity, an increased safety profile (including improved crop tolerance), improved physicochemical properties, or increased biodegradability). In one embodiment, the present invention relates to an agrochemical composition comprising the compound of formula (I), salts, stereoisomers, tautomers, polymorphs or A-oxides thereof, optionally with one or more additional active ingredients with the auxiliary such as an inert carrier or any other essential ingredient such as surfactants, additives, solid diluents, and liquid diluents.

[0278] In another embodiment, the present invention relates to an agrochemical composition which comprises a fungicidally effective amount of a compound of formula (I) in such an amount that can vary in a broad range and is dependent on various factors, such as the fungal species to be controlled, the treated cultivated plant, stored product, harvest or material, the climatic conditions and the specific compounds of formula (I) used.

[0279] The invention also relates to agrochemical compositions comprising an auxiliary and at least one compound of formula (I).

[0280] The compounds of formula (I) 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 the known manner 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 (W G), 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. 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.

[0281] Such compositions may be produced in a 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 adjuvant 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 adjuvant 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.

[0282] The compound or composition of formula (I) of the present invention is usually mixed with an inert carrier such as a solid carrier, a liquid carrier, or a gaseous carrier, and if necessary, a surfactant or other auxiliary agent is added to form an emulsion. Formulated into oils, powders, granules, wettable powders, granule wettable powders, flowable agents, dry flowable agents, microcapsules, aerosol agents, poison bait agents, resin preparations, paste-like preparations, foaming agents, carbon dioxide gas preparations, etc. is used. These preparations may be processed and used as mosquito coils, electric mosquito repellent mats, liquid mosquito repellent preparations, fumigants, fumigants, and sheet preparations. These formulations usually contain 0.01 to 95% by weight of the compound or composition of formula (I) of the present invention.

[0283] Suitable agricultural adjuvants and carriers that are useful in formulating the compositions of the invention in the formulation types described above are well known to those skilled in the art.

[0284] In addition, the compositions of the invention may also be applied with one or more systemically acquired resistance inducers (“SAR” inducer). SAR inducers are known and described in, for example, United States Patent No. US 6,919,298 and include, for example, salicylates and the commercial SAR inducer acibenzolar-S-methyl. The compounds of formula (I) are normally used in the form of agrochemical compositions and can be applied to the crop area or plant to be treated, simultaneously or in succession with further compounds. These further compounds can be e.g. fertilizers or micronutrient donors or other preparations, which influence the growth of plants. They can also be selective herbicides or non-selective herbicides as well as insecticides, fungicides, bactericides, nematicides, molluscicides, or mixtures of several of these preparations, if desired together with further carriers, surfactants or application promoting adjuvants customarily employed in the art of formulation.

[0285] The application can be carried out before or during sowing.

[0286] Methods for applying the compound of formula (I), the combination, and the composition thereof, respectively, are applied onto plant propagation material, especially seeds, including dressing, coating, pelleting, dusting, and soaking as well as in -furrow application methods. Preferably, the compound of formula (I), the combination, and the composition thereof, respectively, are applied to the plant propagation material by a method such that germination is not induced, e. g. by seed dressing, pelleting, coating, and dusting.

[0287] When employed in plant protection, the amounts of active substances applied are, depending on the kind of effect desired, from 0.001 to 5 kg per ha, preferably from 0.005 to 3 kg per ha, more preferably from 0.05 to 1.0 kg per ha, and in particular from 0.1 to 1.0 kg per ha.

[0288] In the treatment of plant propagation materials such as seeds, e.g. by dusting, coating or drenching seeds, amounts of the active substance from 0.1 to 5000 g, preferably from 1 to 1000 g, more preferably from 1 to 100 g per 100 kg of plant propagation material (preferably seeds) are generally required. When used in the protection of materials or stored products, the amount of active substance applied depends on the kind of application area and on the desired effect. Amounts customarily applied in the protection of materials are 0.001 g to 5 kg, preferably 0.005 g to 1 kg, of active substance per cubic meter of the treated material.

[0289] Various types of oils, adjuvants, fertilizer, or micronutrients, and further pesticides (e.g. herbicides, insecticides, fungicides, growth regulators, safeners, biopesticides) may be added to the active substances or the compositions comprising them as premix or, if appropriate, not until immediately prior to use (tank mix). These agents can be mixed with the composition according to the invention in a weight ratio of 1:500 to 500: 1, preferably 1: 100 to 100: 1.

[0290] The compounds of formula (I) may be used in the form of compositions for controlling or protecting against damaging pest and / or phytopathogenic microorganisms, comprising as active ingredient at least one compound of formula (I) or at least one preferred individual compound as defined herein, in free form or agrochemically usable salt form, and at least one of the above-mentioned adjuvants.

[0291] The invention, therefore, provides a composition comprising at least one compound formula (I) an agriculturally acceptable carrier, and optionally an adjuvant. An agriculturally acceptable carrier is for example, a carrier that is suitable for agricultural use. Agricultural carriers are well known in the art. Preferably, said composition may comprise at least one or more pesticidal-active compounds, for example, an additional fungicidal active ingredient in addition to the compound of formula (I).

[0292] The user applies the composition according to the invention usually from a predosage device, a knapsack sprayer, a spray tank, a spray plane, a drone or an irrigation system. Usually, the agrochemical composition is made up with water, buffer, and / or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained. Usually, 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.

[0293] The compound of formula (I) may be the sole active ingredient of a composition or it may be admixed with one or more additional active ingredients, such as a pesticide, fungicide, insecticide, herbicide, or plant growth regulator where appropriate.

[0294] Examples of suitable additional active ingredients include the following: acycloamino acid fungicides, aliphatic nitrogen fungicides, amide fungicides, anilide fungicides, antibiotic fungicides, aromatic fungicides, arsenical fungicides, aryl phenyl ketone fungicides, benzamide fungicides, benzanilide fungicides, benzimidazole fungicides, benzothiazole fungicides, botanical fungicides, bridged diphenyl fungicides, carbamate fungicides, carbanilate fungicides, conazole fungicides, copper fungicides, dicarboximide fungicides, dinitrophenol fungicides, dithiocarbamate fungicides, dithiolane fungicides, furamide fungicides, furanilide fungicides, hydrazide fungicides, imidazole fungicides, mercury fungicides, morpholine fungicides, organophosphorous fungicides, organotin fungicides, oxathiin fungicides, oxazole fungicides, phenylsulfamide fungicides, polysulfide fungicides, pyrazole fungicides, pyridine fungicides, pyrimidine fungicides, pyrrole fungicides, quaternary ammonium fungicides, quinoline fungicides, quinone fungicides, quinoxaline fungicides, strobilurin fungicides, sulfonanilide fungicides, thiadiazole fungicides, thiazole fungicides, thiazolidine fungicides, thiocarbamate fungicides, thiophene fungicides, triazine fungicides, triazole fungicides, triazolopyrimidine fungicides, urea fungicides, valinamide fungicides, and zinc fungicides.

[0295] The active ingredient mixture of the compounds of formula (I) and an active ingredient as described above are preferably in a mixing ratio of from 1000: 1 to 1:5000, especially from 500: 1 to 1:500, more especially in a ratio of from 100: 1 to 1: 100. Those mixing ratios are by weight.

[0296] The mixtures as described above can be used in a method for controlling pests, which comprises applying a composition comprising a mixture as described above to the pests or their environment. The mixtures comprising a compound of formula (I) and one or more active ingredients as described above can be applied, for example, in a single “ready-mix” form, in a combined spray mixture composed of separate formulations of the single active ingredient components, such as a “tank-mix”, and in the combined use of the single active ingredients when applied sequentially, i.e. one after the other with a reasonably short period, such as a few hours or days. The order of applying the compounds of formula (I) and the active ingredient(s) as described above is not essential for working the present invention. When applying the compounds of formula (I) and a pesticidally active substance sequentially the time between both applications may vary e.g. between 2 hours to 7 days. Also, a broader range is possible ranging from 0.25 hours to 30 days, preferably from 0.5 hours to 14 days, particularly from 1 hour to 7 days or from 1.5 hours to 5 days, even more preferred from 2 hours to 1 day. In the binary mixtures and the composition according to the invention the weight ratio of component 1) and the component 2) generally depends on the properties of the active components used, usually, it is in the range of 1: 1000 to 1000: 1, often in the range of 1: 100 to 100: 1.

[0297] The compositions according to the invention are prepared in a manner known per se, in the absence of auxiliaries for example by grinding, screening and / or compressing a solid active ingredient, and in the presence of at least one auxiliary for example by intimately mixing and / or grinding the active ingredient with the auxiliary (auxiliaries). These processes for the preparation of the compositions and the use of the compounds of formula (I) for the preparation of these compositions are also a subject of the invention.

[0298] The compounds and compositions of the present invention are thus useful agronomically for protecting field crops from phytophagous invertebrate pests, and also nonagronomically for protecting other horticultural crops and plants from phytophagous invertebrate pests. This utility includes protecting crops and other plants (i.e. both agronomic and nonagronomic) that contain genetic material introduced by genetic engineering (i.e. transgenic) or modified by mutagenesis to provide advantageous traits. Compounds of the present invention are characterized by favorable metabolic and / or soil residual patterns and exhibit activity controlling a spectrum of agronomic and non-agronomic invertebrate pests. The compounds of the present invention are preventively and / or curatively valuable active ingredients in the field of pest control, even at low rates of application, which can be used against pesticide-resistant pests such as insects and fungi, and / or have a very favorable biocidal spectrum and are well tolerated by warm-blooded species, fish and plants.

[0299] In another embodiment, the compounds of formula (I) and the composition according to the invention are suitable as fungicides. They are distinguished by their effectiveness against a broad spectrum of phytopathogenic fungi, including soil-borne fungi, which derive especially from the classes of the Plasmodiophoromycetes, Peronosporomycetes (syn. Oomycetes), Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, and Deuteromycetes. Some are systemically effective and can be used in crop protection as foliar fungicides, fungicides for seed dressing, and soil fungicides. Moreover, they are suitable for controlling harmful fungi, which inter alia occur in wood or roots of plants.

[0300] The compounds of formula (I) and the compositions thereof are preferably useful in the control of phytopathogenic fungi and insects on various cultivated plants, such as cereals, e. g. wheat, rye, barley, triticale, oats, or rice; beet, fruits, leguminous plants such as soybean, oil plants, cucurbits, fiber plants, citrus fruits, vegetables, lauraceous plants, energy and raw material plants, com; tobacco; nuts; coffee; tea; bananas; vines (table grapes and grape juice grapevines); natural rubber plants; or ornamental and forestry plants; on the plant propagation material, such as seeds; and on the crop material of these plants. According to the invention, all of the above -cultivated plants are understood to comprise all species, subspecies, variants, varieties, and / or hybrids which belong to the respective cultivated plants, including but not limited to winter and spring varieties, in particular in cereals such as wheat and barley, as well as oilseed rape, e.g. winter wheat, spring wheat, winter barley etc.

[0301] Com is also known as Indian com or maize (Zea mays) which comprises all kinds of com such as field com and sweet com. According to the invention, all soybean cultivars or varieties are comprised, in particular indeterminate and determinate cultivars or varieties.

[0302] The term "cultivated plants" is to be understood as including plants which have been modified by breeding, mutagenesis or genetic engineering including but not limiting to agricultural biotech products on the market or in development.

[0303] Genetically modified plants are plants, which genetic material has been so modified by the use of recombinant DNA techniques that under natural circumstances cannot readily be obtained by cross breeding, mutations or natural recombination. Typically, one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant. Such genetic modifications also include but are not limited to targeted post -translational modification of protein(s), oligo or polypeptides for example, by glycosylation or polymer additions such as prenylated, acetylated or famesylated moieties or PEG moieties.

[0304] Plants that have been modified by breeding, mutagenesis or genetic engineering, for example, have been rendered tolerant to applications of specific classes of herbicides, such as auxin herbicides such as dicamba or 2,4-D; bleacher herbicides such as hydroxylphenylpyruvate dioxygenase (HPPD) inhibitors or phytoene desaturase (PDS) inhibitors; acetolactate synthase (ALS) inhibitors such as sulfonyl ureas or imidazolinones; enolpyruvylshikimate-3-phosphate synthase (EPSPS) inhibitors, such as glyphosate; glutamine synthetase (GS) inhibitors such as glufosinate; protoporphyrinogen-IX oxidase inhibitors; lipid biosynthesis inhibitors such as acetyl CoA carboxylase (ACCase) inhibitors; or oxynil (i. e. bromoxynil or ioxynil) herbicides as a result of conventional methods of breeding or genetic engineering. Furthermore, plants have been made resistant to multiple classes of herbicides through multiple genetic modifications, such as resistance to both glyphosate and glufosinate or to both glyphosate and a herbicide from another class such as ALS inhibitors, HPPD inhibitors, auxin herbicides, or ACCase inhibitors. These herbicide resistance technologies are e. g. described in Pest Managem. Sci. 61, 2005, 246; 61, 2005, 258; 61, 2005, 277; 61, 2005, 269; 61, 2005, 286; 64, 2008, 326; 64, 2008, 332; Weed Sci. 57, 2009, 108; Austral. J. Agricult. Res. 58, 2007, 708; Science 316, 2007, 1185; and references quoted therein. Several cultivated plants have been rendered tolerant to herbicides by conventional methods of breeding (mutagenesis), for example Clearfield® summer rape (Canola, BASF SE, Germany) being tolerant to imidazolinones, for example imazamox, or ExpressSun® sunflowers (DuPont, USA) being tolerant to sulfonyl ureas, for example tribenuron. Genetic engineering methods have been used to render cultivated plants such as soybean, cotton, com, beets and rape, tolerant to herbicides such as glyphosate and glufosinate, some of which are commercially available under the trade names RoundupReady® (glyphosate-tolerant, Monsanto, U. S. A.), Cultivance® (imidazolinone tolerant, BASF SE, Germany) and LibertyLink® (glufosinate-tolerant, Bayer CropScience, Germany).

[0305] Furthermore, plants capable to synthesize one or more insecticidal proteins, especially those known from the bacterial genus (Bacillus), by the use of recombinant DNA techniques are within the scope of the present invention. The Bacillus are particularly from Bacillus thuringiensis, such as δ-endotoxins. e.g. CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA, CrylllB(bl) or Cry9c; vegetative insecticidal proteins (VIP), e. g. VIP1, VIP2, VIP3 or VIP3A; insecticidal proteins of bacteria colonizing nematodes, e. g. Photorhabdus spp. or Xenorhabdus spp.; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins, or other insect -specific neurotoxins; toxins produced by fungi, such Streptomycetes toxins, plant lectins, such as pea or barley lectins; agglutinins; proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such as 3-hydroxysteroid oxidase, ecdysteroid-IDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase; ion channel blockers, such as blockers of sodium or calcium channels; juvenile hormone esterase; diuretic hormone receptors (helicokinin receptors); stilbene synthase, bibenzyl synthase, chitinases or glucanases. In the context of the present invention these insecticidal proteins or toxins are to be understood expressly also as pre-toxins, hybrid proteins, truncated or otherwise modified proteins. Hybrid proteins are characterized by a new combination of protein domains, (see, e. g. W002 / 015701). Further examples of such toxins or genetically modified plants capable of synthesizing such toxins are disclosed, for example, in EP374753, WO93 / 007278, WO95 / 34656, EP427529, EP451878, W003 / 18810 and W003 / 52073. The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e. g. in the publications mentioned above. These insecticidal proteins contained in the genetically modified plants impart to the plants, producing these proteins, tolerance to harmful pests from all taxonomic groups of arthropods, especially to beetles (Coeloptera), two-winged insects (Diptera), and moths (Lepidoptera) and to nematodes (Nematoda). Genetically modified plants capable to synthesize one or more insecticidal proteins are, e. g., described in the publications mentioned above, and some of which are commercially available such as YieldGard® (com cultivars producing the CrylAb toxin), YieldGard® Plus (com cultivars producing CrylAb and Cry3Bbl toxins), Starlink® (com cultivars producing the Cry9c toxin), Herculex® RW (com cultivars producing Cry34Abl, Cry35Abl and the enzyme phosphinothricin-A-acetyltransferase [PAT]); NuCOTN® 33B (cotton cultivars producing the CrylAc toxin), Bollgard® I (cotton cultivars producing the Cryl Ac toxin), Bollgard® II (cotton cultivars producing CrylAc and Cry2Ab2 toxins); VIPCOT® (cotton cultivars producing a VIP-toxin); NewLeaf®(potato cultivars producing the Cry3A toxin); Bt-Xtra®, NatureGard®, KnockOut®, BiteGard®, Protecta®, Btl 1 (e. g. Agrisure® CB) and Btl76 from Syngenta Seeds SAS, France, (com cultivars producing the CrylAb toxin and PAT enyzme), MIR604 from Syngenta Seeds SAS, France (com cultivars producing a modified version of the Cry3A toxin, c.f. WO 03 / 018810), MON 863 from Monsanto Europe S. A., Belgium (com cultivars producing the Cry3Bbl toxin), IPC 531 from Monsanto Europe S. A., Belgium (cotton cultivars producing a modified version of the CrylAc toxin) and 1507 from Pioneer Overseas Corporation, Belgium (com cultivars producing the Cryl F toxin and PAT enzyme); Btl 1 Maize from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10. Genetically modified Zea mays which has been rendered resistant to attack by the European com borer (Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of a truncated CrylAb toxin. Btll maize also transgenically expresses the enzyme PAT to achieve tolerance to the herbicide glufosinate ammonium; Btl76 Maize from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10. Genetically modified Zea mays which has been rendered resistant to attack by the European com borer (Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of a CrylAb toxin. Btl76 maize also transgenically expresses the enzyme PAT to achieve tolerance to the herbicide glufosinate ammonium; MIR604 Maize from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10. Maize which has been rendered insect-resistant by transgenic expression of a modified Cry3A toxin. This toxin is Cry3A055 modified by insertion of a cathepsin-G-protease recognition sequence. The preparation of such transgenic maize plants is described in WO 03 / 018810; 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 Cry3Bbl toxin and has resistance to certain Coleoptera insects; IPC 531 Cotton from Monsanto Europe S. A. 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C / ES / 96 / 02; 1507 Maize from Pioneer Overseas Corporation, Avenue Tedesco, 7 B-l 160 Brussels, Belgium, registration number C / NL / 00 / 10. Genetically modified maize for the expression of the protein Cryl F for achieving resistance to certain Lepidoptera insects and of the PAT protein for achieving tolerance to the herbicide glufosinate ammonium; and NK603 x MON 810 Maize from Monsanto Europe S. A. 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C / GB / 02 / M3 / 03. Consists of conventionally bred hybrid maize varieties by crossing the genetically modified varieties NK603 and MON 810. NK603 x MON 810 Maize transgenically expresses the protein CP4 EPSPS, obtained from Agrobacterium sp. strain CP4, which imparts tolerance to the herbicide Roundup® (contains glyphosate), and also a Cryl Ab toxin obtained from Bacillus thuringiensis subsp. kurstaki which brings about tolerance to certain Lepidoptera, include the European com borer.

[0306] Furthermore, plants capable to synthesize one or more proteins to increase the resistance or tolerance of those plants to bacterial, viral or fungal pathogens by the use of recombinant DNA techniques are also within the scope of the present invention. Examples of such proteins are the so-called "pathogenesis-related proteins" (PR proteins, see, for example EP0392225), plant disease resistance genes (e.g. potato cultivars, which express resistance genes acting against Phytophthora infestans derived from the Mexican wild potato Solcinum bulbocastanum) or T4-lysozym (e. g. potato cultivars capable of synthesizing these proteins with increased resistance against bacteria such as Erwinia amylvora). The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e. g. in the publications mentioned above.

[0307] Furthermore, plants capable to synthesize one or more proteins, by the use of recombinant DNA techniques, to increase the productivity (e. g. biomass production, grain yield, starch content, oil content or protein content), tolerance to drought, salinity or other growth-limiting environmental factors or tolerance to pests and fungal, bacterial or viral pathogens of those plants are within the scope of the present invention.

[0308] Furthermore, plants that contain a modified amount of substances of content or new substances of content, by the use of recombinant DNA techniques, to improve human or animal nutrition, e.g. oil crops that produce health-promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (e. g. Nexera® rape, DOW Agro Sciences, Canada) are also within the scope of the present invention. Furthermore, plants that contain a modified amount of substances of content or new substances of content, by the use of recombinant DNA techniques, to improve raw material production, e.g. potatoes that produce increased amounts of amylopectin (e. g. Amflora® potato, BASF SE, Germany) are also within the scope of the present invention.

[0309] The compounds of formula (I) are effective against fungi and fungal vectors of disease as well as phytopathogenic bacteria and viruses. These fungi and fungal vectors of disease as well as phytopathogenic bacteria and viruses are for example:

[0310] Absidia corymbifera, Alternaria spp., Aphanomyces spp., Ascochyta spp., Aspergillus spp. including A. flavus, A. fumigatus. A. nidulans, A. niger. A. terms, Aureobasidium spp. including A. pullulans, Blastomyces dermatitidis, Blumeria graminis, Bremia lactucae, Botryosphaeria spp. including B. dothidea, B. obtusa, Botrytis spp. including B. cine re a. 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, Colletotrichum capsid, 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, Parastagonospora nodorum, 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, Pythium spp. 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, Septoria lycopersici, Sphaerotheca macularis, Sphaerotheca fusca (Sphaerotheca fuliginea), Sporothorix spp, Stagonospora nodorum, Stemphylium spp., Stereum hirsutum, Thanatephorus cucumeris, Thielaviopsis basicola, Tilleda 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, Ustilaginales such as Ustilaginoidea virens, Ustilago nuda, Ustilago tritici, Ustilago zeae, Cerotelium fici, Chrysomyxa arctostaphyli, Coleosporium ipomoeae, Hemileia vastatrix, Puccinia arachidis, Puccinia cacabata, Puccinia graminis, Puccinia sorghi, Puccinia striiformis f.sp. Hordei, Puccinia striiformis f.sp. Secalis, Pucciniastrum coryli, or Uredinales such as Cronartium ribicola, Gymnosporangium juniperi-virginianae, Melampsora medusae, Phragmidium mucronatum, Physopella ampelosidis, Tranzschelia discolor and Uromyces viciae-fabae, Cryptococcus spp., Exobasidium vexans, Marasmiellus inoderma, Mycena spp., Sphacelotheca reiliana, Typhula ishikariensis, Urocystis agropyri, Itersonilia perplexans, Corticium invisum, Waitea circinata, Rhizoctonia solani, Thanetephorus cucurmeris, Entyloma dahliae, Entylomella microspora, Neovossia moliniae and Tilletia caries, Blastocladiomycetes, such as Physoderma maydis, Mucoromycetes, such as Choanephora cucurbitarum. The compound of formula (I), the combination or the composition thereof may be used to treat several fungal pathogens. Non-limiting examples of pathogens of fungal diseases that can be treated in accordance with the invention include:

[0311] Ustilaginales such as Ustilaginoidea virens, Ustilago nuda, Ustilago tritici, Ustilago zeae, rusts for example those caused by Pucciniales such as Cerotelium fid, Chrysomyxa arctostaphyli, Coleosporium ipomoeae, Hemileia vastatrix, Puccinia arachidis, Puccinia cacabata, Puccinia graminis, Puccinia recondita, Puccinia sorghi, Puccinia hordei, Puccinia striiformis f.sp. Hordei, Puccinia striiformis f.sp. Secalis, Pucciniastrum coryli, or Uredinales such as Cronartium ribicola.

[0312] Gymnosporangium juniperi-virginianae, 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, Urocystis agropyri, Itersonilia perplexans, Corticium invisum, Laetisaria fuciformis, Waitea circinata, Rhizoctonia solani, Thanetephorus cucurmeris, Entyloma dahliae, Entylomella microspora, Neovossia moliniae and Tilletia caries. Blastocladiomycetes, such as Physoderma maydis. Mucoromycetes. such as Choanephora cucurbitarum; Mucor spp.; and Rhizopus arrhizus.

[0313] In another embodiment, disease caused by rust disease pathogens, for example, Gymnosporangium species, for example, Gymnosporangium sabinae; Hemileia species, for example, Hemileia vastatrix Phakopsora species, for example, Phakopsora pachyrhizi or Phakopsora meibomiae; Puccinia species, for example, Puccinia recondita, Puccinia graminis or Puccinia striiformis; Uromyces species, for example, Uromyces appendiculatus;

[0314] Plants which can be treated in accordance with the invention include the following: cotton, flax, grapevine, fruits, vegetables, such as Rosaceae sp. (for example pome fruits such as apples, pears, apricots, cherries, almonds and peaches), Ribesioidae sp., Juglandaceae sp., Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceae sp., Actinidaceae sp., Lauraceae sp., Musaceae sp. (for example banana trees and plantations), Rubiaceae sp. (for example coffee), Theaceae sp., Sterculiceae sp., Rutaceae sp. (for example lemons, oranges and grapefruit); Vitaceae sp. (for example grapes); Solanaceae sp. (for example tomatoes, peppers), Liliaceae sp., Asteraceae sp. (for example lettuce), Umbelliferae sp., Cruciferae sp., Chenopodiaceae sp., Cucurbitaceae sp. (for example cucumber), Alliaceae sp. (for example leek, onion), Papilionaceae sp. (for example peas); major crop plants, such as Poaceae / Gramineae sp. (for example maize, turf, cereals such as wheat, rye, rice, barley, oats, millet and triticale), Asteraceae sp. (for example sunflower), Brassicaceae sp. (for example white cabbage, red cabbage, broccoli, cauliflower, Brussels sprouts, pak choi, kohlrabi, radishes, and oilseed rape, mustard, horseradish and cress), Fabacae sp. (for example bean, peanuts), Papilionaceae sp. (for example soyabean), Solanaceae sp. (for example potatoes), Chenopodiaceae sp. (for example sugar beet, fodder beet, swiss chard, beetroot); Malvaceae (for example cotton); useful plants and ornamental plants for gardens and wooded areas; and genetically modified varieties of each of these plants.

[0315] More preference is given to controlling the following diseases of soya beans: Fungal diseases on leaves, stems, pods, and seeds caused, for example, by Altemaria leaf spot (Altemaria spec, atrans tenuissima), Anthracnose (Colletotrichum gloeosporoides dematium var. truncatum), brown spot (Septaria glycines), cercospora leaf spot and blight ( Cercospora kikuchii), choanephora leaf blight (Choanephora infundibulifera trispora (Syn.)), dactuliophora leaf spot (Dactuliophora glycines, downy mildew (Peronospora manshurica), drechslera blight (Drechslera glycini), frogeye leaf spot (Cercospora sojina), leptosphaerulina leaf spot (Leptosphaerulina trifolii), phyllostica leaf spot (Phyllosticta sojaecola), pod and stem blight (Phomopsis sojae), powdery mildew (Microsphaera diffusa), pyrenochaeta leaf spot (Pyrenochaeta glycines, rhizoctonia aerial, foliage, and web blight (Rhizoctonia solani), rust (Phakopsora pachyrhizi, Phakopsora meibomiae), scab (Sphaceloma glycines, stemphylium leaf blight (Stemphylium botryosum), target spot (Corynespora cassiicola).

[0316] Fungal diseases on roots and the stem base caused, for example, by black root rot (Calonectiia crotalariae), charcoal rot (Macrophomina phaseolina), fusarium blight or wilt, root rot, and pod and collar rot (Fusarium oxysporum, Fusarium orthoceras, Fusarium semitectum, Fusarium equiseti), mycoleptodiscus root rot (My colept odi sens terrestris), neocosmospora (Neocosmospora vasinfecta), pod and stem blight (Diaporthe phaseolorum), stem canker (Diaporthe phaseolorum var. caulivora), phytophthora rot (Phytophthora megasperma), brown stem rot (Phialophora gregata), pythium rot (Pythium aphanidennatum, Pythium irregulare, Pythium debaryanum, Pythium myriotylum, Pythium ultimum), rhizoctonia root rot, stem decay, and damping-off (Rhizoctonia solani), sclerotinia stem decay (Sclerotinia sclerotiorum), sclerotinia southern blight (Sclerotinia rolfsii), thielaviopsis root rot (Thielaviopsis basicola).

[0317] The present invention also relates to the use of the compounds of formula (I), the combination or the composition thereof for combating the following pathogens of fungal diseases which can be treated in accordance with the invention include the diseases caused by rust disease pathogens, for example Gymnosporangium species, for example Gymnosporangium sabinae,' Hemileia species, for example Hemileia vastatrix,' Phakopsora species, for example Phakopsora pachyrhizi or Phakopsora meibomiae,' Puccinia species, for example Puccinia recondita, Puccinia graminis oder Puccinia striiformis,' Uromyces species, for example Uromyces appendiculatus. In particular, Cronartium ribicola (White pine blister rust); Gymnosporangium juniperi-virginianae (Cedar-apple rust); Hemileia vastatrix (Coffee rust); Phakopsora meibomiae and P. pachyrhizi (Soybean rust); Puccinia coronata (Crown Rust of Oats and Ryegrass); Puccinia graminis (Stem rust of wheat and Kentucky bluegrass, or black rust of cereals); Puccinia hemerocallidis (Daylily rust); P. hordei (dwarf rust), Puccinia persistens subsp. triticina (wheat rust or 'brown or red rust'); P. recondita (brown or leaf rust) on cereals, such as e. g. wheat, barley or rye; Puccinia sorghi (rust in com); Puccinia striiformis ('Yellow rust' in cereals); Puccinia melanocephala ('Brown rust' in sugarcane); Puccinia kuehnii ('Orange rust' in sugarcane); Uromyces appendiculatus (rust of beans); Uromyces phaseoli (Bean rust).

[0318] The compounds of formula (I) and compositions thereof, respectively, are particularly suitable for controlling the following causal agents of plant diseases: rusts on soybean and cereals (e.g. Phakopsora pachyrhizi and P. meibomiae on soybean; Puccinia tritici and P. striiformis on wheat); molds on specialty crops, soybean, oil seed rape and sunflowers (e.g. Botrytis cinerea on strawberries and vines, Sclerotinia sclerotiorum, S. minor and S. rolfsii on oil seed rape, sunflowers, and soybean); Fusarium diseases on cereals (e.g. Fusarium culmorum and F. graminearum on wheat); downy mildews on specialty crops (e.g. Plasmopara viticola on vines, Phytophthora infestans on potatoes); downy mildew on various plants, e. g. Pseudoperonospora cubensis on cucurbits or P. humili on hop; Pseudopezicula tracheiphila (red fire disease or.rotbrenner', anamorph: Phialophord) on vines; Mycosphaerella spp. on cereals, bananas, soft fruits and ground nuts, such as e. g. M. graminicola (anamorph: Septoria tritici, Septoria blotch) on wheat or M. fijiensis (black Sigatoka disease) on bananas; powdery mildews on specialty crops and cereals (e.g. Uncinula necator on vines, Erysiphe spp. on various specialty crops, Blumeria graminis on cereals); and leaf spots on cereals, soybean, and com (e.g. Septoria tritici and S. nodorum on cereals, S. glycines on soybean, Cercospora spp. on com and soybean).

[0319] In one embodiment, the compounds of formula (I) have broad ranges of activity against fungal pathogens. Exemplary pathogens may include, but are not limited to, causing agent of wheat leaf blotch (Zymoseptoria tritici), wheat brown rust (Puccinia triticina), wheat stripe rust (Puccinia striiformis), scab of apple (Venturia inaequalis), powdery mildew of grapevine (Uncinula necator), barley scald (Rhynchosporium secalis), blast of rice (Pyricularia oryzae), rust of soybean (Phakopsora pachyrhizi), glume blotch of wheat (Leptosphaeria nodorum), powdery mildew of wheat (Blumeria graminis f. sp. tritici), powdery mildew of barley (Blumeria graminis f. sp. hordei), powdery mildew of cucurbits (Erysiphe cichoracearum, Erysiphe graminis), anthracnose of cucurbits (Colletotrichum lagenarium), leaf spot of beet (Cercospora beticola), leaf spot of tomato (Corynespora cassiicola), early blight of tomato (Alternaria solani), and spot blotch of barley (Cochliobolus sativus).

[0320] The compounds of formula (I), as well as compositions or combinations comprising compounds of formula (I), are effective against a broad spectrum of phytopathogenic fungi, including but not limited to, rust diseases caused by Phakopsora pachyrhizi, leaf spot diseases caused by Septoria spp., Cercospora spp., and Corynespora spp., mold diseases caused by Botrytis cinerea, Sclerotinia sclerotiorum, and Rhizoctonia spp., downy mildew diseases caused by Phytophthora infestans and Plasmopara viticola. The compounds of formula (I), as well as compositions or combinations comprising compounds of formula (I), are effective for protecting a variety of crops, including but not limited to soybean, cereals, beets, com, grapes, oilseed rape, rice, potato, and tomato.

[0321] In one aspect, the present invention relates to the method of protecting plants susceptible to and / or under attack by phytopathogenic fungi containing an amino acid substitution of F129L in the mitochondrial cytochrome b protein conferring resistance to Qo inhibitors, which method comprises applying to said plants, treating plant propagation material of said plants with, and / or applying to said phytopathogenic fungi, at least one compound of formula (I) or a composition thereof.

[0322] According to another embodiment, the method for combating phytopathogenic fungi comprises: a) identifying the phytopathogenic fungi containing an amino acid substitution F 129L in the mitochondrial cytochrome b protein conferring resistance to Qo inhibitors, or the materials, plants, the soil, or seeds that are at risk of being diseased from phytopathogenic fungi as defined herein, and b) treating said fungi or the materials, plants, the soil or plant propagation material with an effective amount of at least one compound of formula (I), or a composition comprising it thereof.

[0323] The term "phytopathogenic fungi an amino acid substitution F129L in the mitochondrial cytochrome b protein conferring resistance to Qo inhibitors" is to be understood that at least 10% of the fungal isolates to be controlled contain such F129L substitution in the mitochon-drial cytochrome b protein conferring resistance to Qo inhibitors, preferably at least 30%, more preferably at least 50%, even more preferably at least 75% of the fungi, most preferably between 90 and 100%; in particular between 95 and 100%. Furthermore, the present invention relates to the use of compounds of formula (I) as defined herein for combating phytopathogenic fungi containing an amino acid substitution F129L in the mitochondrial cytochrome b protein conferring resistance to Qo inhibitors.

[0324] "Qo inhibitor," as used herein, includes any substance that is capable of diminishing and / or inhibiting respiration by binding to a ubihydroquinone oxidation center of a cytochrome bc1complex in mitochondria. The oxidation center is typically located on the outer side of the inner mitochondrial membrane.

[0325] The mutation F 129L in the cytochrome b (cytb, also referred to as cob) gene shall mean any substitution of nucleotides of codon 129 encoding "F" (phenylalanine; e.g. TTT or TTC) that leads to a codon encoding "L" (leucine; e.g. TTA, TTG, TTG, CTT, CTC, CTA or CTG), for example, the substitution of the first nucleotide of codon 129 T to 'C (TTT to CTT), in the cytochrome b gene resulting in a single amino acid substitution in the position 129 from F (phenylalanine) to L (leucine) (F129L) in the cytochrome b protein (Cytb). In the present invention, the mutation F129L in the cytochrome b gene shall be understood to be a single amino acid substitution in position 129 from F (phenylalanine) to L (leucine) (F129L) in the cytochrome b protein. Many other phytopathogenic fungi acquired the F129L mutation in the cytochrome b gene conferring resistance to Qo inhibitors, such as rusts, in particular soybean rust (Phakopsora pachyrhizi and Phakopsora meibromiae) as well as fungi from the genera Altemaria, Pyrenophora and Rhizoctonia. Preferred fungal species are Alternaria solani, Phakopsora pachyrhizi, Phakopsora meibromiae, Pyrenophora teres, Pyrenophora tritici-repentis. Zymoseptoria tritici, Corynespora spp. Cercospora spp. and Rhizoctonia solani,' in particular, Phakopsora pachyrhizi.

[0326] In one aspect, the present invention relates to the method of protecting plants susceptible to and / or under attack by phytopathogenic fungi containing an amino acid substitution of G143A in the mitochondrial cytochrome b protein conferring resistance to Qo inhibitors, which method comprises applying to said plants, treating plant propagation material of said plants with, and / or applying to said phytopathogenic fungi, at least one compound of formula (I) or a composition comprising it thereof.

[0327] The compounds of formula (I) and composition comprising it thereof, respectively, are also suitable for controlling harmful pest and / or microorganisms in the protection of stored products or harvest, and in the protection of materials.

[0328] The compounds of formula (I) are employed as such or in form of compositions by treating the fungi, the plants, and plant propagation materials, such as seeds; soil, surfaces, materials, or rooms to be protected from fungal attack with a fungicidally effective amount of the active substances. The application can be carried out both before and after the infection of the plants, plant propagation materials, such as seeds; soil, surfaces, materials or rooms by the fungi.

[0329] These young plants may also be protected before transplantation by a total or partial treatment by immersion or pouring.

[0330] Preferably, a treatment of plant propagation materials with the compound of formula (I), the combination and or the composition thereof, respectively, is used for controlling a multitude of fungi on cereals, such as wheat, rye, barley, and oats; rice, com, cotton, and soybeans.

[0331] The present invention also relates to a method for combating infestation of plants by phytopathogenic micro-organisms in agricultural crops and or horticultural crops wherein an effective amount of at least one compound of formula (I) or the combination of the present invention or the composition of the present invention, is applied to the seeds of plants. The compound, the combination, and the composition of the present invention can be used for combating plant diseases.

[0332] The compound of formula (I), the combinations, and the composition thereof, respectively, are also suitable for controlling harmful fungi in the protection of stored products or harvest and the protection of materials. The term "protection of materials" is to be understood to denote the protection of technical and non-living materials, such as adhesives, glues, wood, paper and paperboard, textiles, leather, paint dispersions, plastics, cooling lubricants, fiber or fabrics, against the infestation and destruction by harmful microorganisms, such as fungi and pest such as insect.

[0333] As to the protection of wood and other materials, particular attention is paid to the following harmful fungi: Ascomycetes such as Ophiostoma spp., Ceratocystis spp., Aureobasidium pullulans, Sclerophoma spp., Chaetomium spp., Humicola spp., Petriella spp., Trichurus spp.; Basidiomycetes such as Coniophora spp., Coriolus spp., Gloeophyllum spp., Lentinus spp., Pleurotus spp., Pora spp., Serpula spp. and Tyromyces spp., Deuteromycetes such as Aspergillus spp., Cladosporium spp., Penicillium spp., Trichoderma spp., Altemaria spp., Paecilomyces spp. and Zygomycetes such asMucor spp., and in addition in the protection of stored products and harvest the following yeast fungi are worthy of note: Candida spp. and Saccharomyces cerevisae.

[0334] In one embodiment, the compound of formula (I), the combination, and the composition thereof, respectively, are particularly suitable for controlling the following plant diseases: Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybeans as well as the leaf spot diseases Cercospora spp. and Corynespora spp.

[0335] The present invention further relates to a method of controlling or preventing infestation of plants by phytopathogenic fungi in agricultural crops or horticultural crops, wherein an effective amount of the compound of formula (I) or the combination or the composition comprising at least one compound of formula (I), is applied to the plants, plant parts or locus thereof, soil, seeds or materials to be protected against fungal attack.

[0336] The compounds of formula (I), the combination, and the composition thereof, respectively, may be used for improving the health of a plant. The invention also relates to a method for improving plant health by treating a plant, its propagation material and / or the locus where the plant is growing or is to grow with an effective amount of the compounds of formula (I) and the composition or combination thereof, respectively.

[0337] The term "plant health" is to be understood to denote a condition of the plant and / or its products which is determined by several indicators alone or in combination with each other such as yield (e. g. increased biomass and / or increased content of valuable ingredients), plant vigor (e. g. improved plant growth and / or greener leaves ("greening effect")), quality (e. g. improved content or composition of certain ingredients) and tolerance to abiotic and / or biotic stress. The above -identified indicators for the health condition of a plant may be interdependent or may result from each other.

[0338] Another aspect of the invention is related to the use of a compound of formula (I) as such or in the form of a composition for treating the fungi or the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms to be protected from fungal attack with a fungicidally effective amount of the active ingredients. The application can be carried out both before and after the infection of the plants, plant propagation materials, such as seeds, soil, surfaces, materials, or rooms by the fungi. Plant propagation materials may be treated with a compound of formula (I), the combination and the composition thereof protectively either at or before planting or transplanting.

[0339] Digital Technologies

[0340] The compounds of the invention can be used in combination with models e.g. embedded in computer programs for site specific crop management, satellite farming, precision farming or precision agriculture. Such models support the site-specific management of agricultural sites with data from various sources such as soils, weather, crops (e.g. type, growth stage, plant health), weeds (e.g. type, growth stage), diseases, pests, nutrients, water, moisture, biomass, satellite data, yield etc. with the purpose to optimize profitability, sustainability and protection of the environment. In particular, such models can help to optimize agronomical decisions, control the precision of pesticide applications and record the work performed.

[0341] As an example, the compounds of the invention can be applied to a crop plant according to an appropriate dose regime if a model models the development of a pest and calculates that a threshold has been reached for which it is recommendable to apply the compound of the invention to the crop plant. Commercially available systems which include agronomic models are e.g. FieldScripts™ from The Climate Corporation, XarvioTMfrom BASF, AGLogic™from John Deere, etc.

[0342] The compounds of the invention can also be used in combination with smart spraying equipment such as e.g. spot spraying or precision spraying equipment attached to or housed within a farm vehicle such as a tractor, robot, helicopter, airplane, unmanned aerial vehicle (UAV) such as a drone, etc. Such an equipment usually includes input sensors (such as e.g. a camera) and a processing unit configured to analyze the input data and configured to provide a decision based on the analysis of the input data to apply the compound of the invention to the crop plants (respectively the weeds) in a specific and precise manner. The use of such smart spraying equipment usually also requires positions systems (e.g. GPS receivers) to localize recorded data and to guide or to control farm vehicles; geographic information systems (GIS) to represent the information on intelligible maps, and appropriate farm vehicles to perform the required farm action such as the spraying.

[0343] For example, pests can be detected from imagery acquired by a camera. In an example the pests can be identified and / or classified based on that imagery. Such identification and / classification can make use of image processing algorithms. Such image processing algorithms can utilize machine learning algorithms, such as trained neutral networks, decision trees and utilize artificial intelligence algorithms. In this manner, the compounds described herein can be applied only where needed.

[0344] Positive crop response:

[0345] The compounds of the present invention not only control microorganisms effectively but also show positive crop response such as plant growth enhancement effects like enhanced root growth, enhanced tolerance to drought, high salt, high temperature, chill, frost or light radiation, improved flowering, enhanced nutrient utilization (such as improved nitrogen assimilation), enhanced quality plant products, higher number of productive tillers, enhanced resistance to insect pests and the like, which results in higher yields.

[0346] Any range or desired value given herein may be extended or altered without losing the effects sought, as is apparent to the skilled person for an understanding of the teachings herein.

[0347] The invention disclosed in the present disclosure shall now be elaborated with the help of non-limiting examples.

[0348] Chemistry Examples:

[0349] The following examples set forth the manner and process of making compounds of the present invention without being a limitation thereof and include the best mode contemplated by the inventors for carrying out the invention.

[0350] Example-1: Synthesis of methyl (Z)-2-(5-(2,3-dihydro-lH-inden-5-yl)-2-methylphenoxy)-3-methoxyacrylate (Compound No. 21)

[0351]

[0352] Step-1: Synthesis of methyl 2-(5-bromo-2-methylphenoxy) acetate

[0353] To a stirred solution of 5 -bromo-2 -methylphenol (10 g, 53.5 mmol) and methyl 2-bromoacetate (7.59 mL, 80 mmol) in tetrahydrofuran (100 mL), potassium carbonate (14.78 g, 107 mmol) was added at 25 °C. The resulting reaction mixture was stirred at 65 °C for 14 h. After completion of the reaction, the reaction mixture was cooled to 25 °C, diluted with water (100 mL), and extracted with ethyl acetate (2 x 100 mL). The combined organic layers were dried over anhydrous sodium sulphate, filtered, and concentrated under reduced pressure to obtain the crude compound, which was purified by flash column chromatography to obtain methyl 2-(5-bromo-2-methylphenoxy)acetate (11.77 g, 45.4 mmol, 85% yield) as a brown viscous liquid.

[0354] ‘H-NMR (400 MHz, DMSO L) 5 7.11 (dd, J= 7.8, 0.5 Hz, 1H), 7.07-7.04 (m, 2H), 4.88 (d, J= 9.3 Hz, 2H), 3.69 (d, J= 4.9 Hz, 3H), 2.15 (d, J= 14.7 Hz, 3H); LCMS: m / z = 259.26. [M+l],

[0355] Step-2: Synthesis of methyl 2-(5-bromo-2-methylphenoxy)-3-hydroxyacrylate

[0356] To a stirred solution of methyl 2-(5-bromo-2-methylphenoxy)acetate (8 g, 30.9 mmol) and methyl formate (11.53 mL, 185 mmol) in tetrahydrofuran (30 mL), sodium methoxide (3.34 g, 61.8 mmol) was added portion-wise under nitrogen atmosphere at 25 °C. The resulting reaction mixture was stirred at 25 °C for 3 h. After completion of the reaction, the reaction mixture was poured into ice-water, neutralized by 1N HCl (pH ~6-7) and extracted with ethyl acetate (2 x 100 mL). The combined organic layers were dried over anhydrous sodium sulphate, filtered, and concentrated under reduced pressure to obtain methyl 2-(5-bromo-2-methylphenoxy)-3-hydroxyacrylate (6.21 g, 21.61 mmol, 70 % yield), as a viscous gum, which was used in the next step without further purification.

[0357] ’H-NMR (400 MHz, CDCh) 3 7.05-7.00 (m, 2H), 6.82 (d, J= 1.5 Hz, 1H), 4.63 (d, J= 5.4 Hz, 2H), 3.81 (s, 3H), 2.25 (d, J= 16.6 Hz, 3H); LCMS: m / z = 288.3. [M+l],

[0358] Step-3: Synthesis of methyl (Z)-2-(5-bromo-2-methylphenoxy)-3-methoxyacrylate

[0359] To a stirred solution of methyl 2-(5-bromo-2-methylphenoxy)-3-hydroxyacrylate (10 g, 34.8 mmol) in N,N-dimethylformamide (30 mL), potassium carbonate (7.22 g, 52.2 mmol) and iodomethane (2.2 mL, 34.8 mmol) were added respectively under nitrogen atmosphere at 25 °C. The reaction mixture was stirred at 25 °C for 6 h. After completion of the reaction, the reaction mixture was diluted with water (100 mL) and extracted with ethyl acetate (2 x 100 mL). The combined organic layers were dried over anhydrous sodium sulphate, filtered, and concentrated under reduced pressure to obtain the crude compound, which was purified by flash column chromatography to obtain methyl (Z)-2-(5-bromo-2-methylphenoxy)-3-methoxyacrylate (6.29 g, 20.90 mmol, 60 % yield) as an off-white solid.

[0360] ’H-NMR (400 MHz, DMSO- d6) 3 7.57 (s, 1H), 7.14 (dd, J= 7.9, 0.6 Hz, 1H), 7.08 (dd, J= 8.1, 2.0 Hz, 1H), 6.78 (d, J= 1.8 Hz, lH), 3.86 (s, 3H), 3.65 (d, J= 7.0Hz, 3H), 2.07 (t, J = 2.9 Hz, 3H); LCMS: m / z = 302.58. [M+l],

[0361] Step-4: Synthesis of methyl (Z)-3-methoxy-2-(2-methyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenoxy)acrylate

[0362]

[0363] To a stirred solution of methyl (Z)-2-(5-bromo-2-methylphenoxy)-3-methoxyacrylate (17 g, 56.5 mmol) and bis(pinacolato) diboron (16.49 g, 64.9 mmol) in 1,4-dioxane (112 mL), potassium acetate (11.08 g, 113 mmol) was added and degassed with nitrogen for 5 min. followed by the addition of dichlorofl, r-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (1.15 g, 1.41 mmol) at 25 °C. The resulting reaction mixture was stirred at 95 °C for 12 h. After completion of the reaction, the reaction mixture was passed through a Celite® pad and washed with ethyl acetate 200 mL. The collected organic layer was washed with water (3 x 200 mL) and brine (2 x 200 mL). The organic layer was dried over anhydrous sodium sulphate, filtered, and concentrated under reduced pressure to obtain the crude compound, which was purified by flash column chromatography to obtain methyl (Z)-3-methoxy-2-(2-methyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenoxy)acrylate (12.2 g, 35.0 mmol, 62.1 % yield) as an off white solid.

[0364] ’H-NMR (400 MHz, CDCh) 5 7.37 (dd, J = 7.3, 0.7 Hz, 1H), 7.32 (s, 1H), 7.16 (d, J = 7.3 Hz, 1H), 7.10 (s, 1H), 3.87 (s, 3H), 3.69 (s, 3H), 2.37 (s, 3H), 1.32 (d, J = 6.4 Hz, 12H); LCMS: m / z = 348.90 [M+l],

[0365] Step-5: Synthesis of methyl (Z)-2-(5-(2,3-dihydro-lH-inden-5-yl)-2-methylphenoxy)-3-methoxyacrylate (Compound No. 21)

[0366] To a stirred solution of methyl (Z)-3-methoxy-2-(2-methyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenoxy)acrylate (400 mg, 1.15 mmol) and 5-bromo-2,3-dihydro-lH-indene (272 mg, 1.38 mmol) in 1,4-dioxane (10 mL) and water (5 mL), K2CO3 (318 mg, 2.29 mmol) was added, and the reaction mixtue was degassed for 5 minutes under a nitrogen atmosphere, followed by the addition of dichlorofl, r-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (94 mg, 0.115 mmol) at 25 °C under nitrogen. The resulting reaction mixture was stirred at 95 °C for 12 h. After completion of the reaction, the reaction mixture was cooled to 25 °C and then passed through a Celite® pad and washed with ethyl acetate (2 x 30 mL). The combined organic layers were washed with water (2 x 25 mL), and brine (2 x 15 mL), the combined organic layers were dried over anhydrous sodium sulphate, filtered, and concentrated under reduced pressure to get the crude compound which was purified by flash column chromatography to obtain methyl (Z)-2-(5-(2,3-dihydro-lH-inden-5-yl)-2-methylphenoxy)-3-methoxyacrylate (140 mg, 0.41 mmol, 36.0 % yield).

[0367] ‘H-NMR (400 MHz, CDCh) 57.35 (s, 1H), 7.34 (s, 1H), 7.28 (d, J = 7.8 Hz, 2H), 7.20 (d, J = 7.8 Hz, 1H), 7.11 (dd, J = 7.8, 1.7 Hz, 1H), 6.90 (d, J = 1.7 Hz, 1H), 3.87 (t, J = 7.1 Hz, 3H), 3.70 (d, J = 2.6 Hz, 3H), 2.94 (q, J = 7.7 Hz, 4H), 2.37 (d, J = 9.3 Hz, 3H), 2.14-2.07 (m, 2H); LCMS: m / z = 338.95.

[0368] [M],

[0369] Example-2: Synthesis of methyl (Z)-2-(5-(2,2-dimethyl-l-oxo-2,3-dihydro-lH-inden-4-yl)-2-methylphenoxy)-3-methoxyacrylate (Compound No. 35)

[0370]

[0371] Step-1: Synthesis of 4-bromo-2,2-dimethyl-2,3-dihydro-lH-inden-l-one

[0372] To a stirred solution of 4-bromo-2,3-dihydro-lH-inden-l-one (1.5 g, 7.11 mmol) in tetrahydrofuran (15 mL), sodium hydride (60 %, 0.71 g, 17.77 mmol) was slowly added under nitrogen atmosphere at 0 °C. The resulting reaction mixture was stirred for 20 min. To this reaction mixture, methyl iodide (2.52 g 17.75 mmol) was added dropwise at 0 °C. The resulting reaction mixture was stirred at 25 °C for 16 h. After completion of the reaction, the reaction mixture was quenched with dropwise addition of saturated ammonium chloride solution at 0 °C, diluted with ethyl acetate (30 mL), washed with water (2 x 30 mL) and brine (20 mL). The organic layer was dried over anhydrous sulphate, filtered, and concentrated under reduced pressure to get the crude compound, which was purified by flash column chromatography to obtain 4-bromo-2,2-dimethyl-2,3-dihydro-lH-inden-l-one (1.31 g, 5.48 mmol, 77 % yield) as a brown gum.

[0373] ’H-NMR (400 MHz, CDCh) 57.77-7.76 (m, 1H), 7.72-7.70 (m, 1H), 7.30-7.28 (m, 1H), 2.94 (s, 2H), 1.25 (s, 3H); GCMS: m / z = 238.1 [M],

[0374] Step-2: Synthesis of methyl (Z)-2-(5-(2,2-dimethyl-l-oxo-2,3-dihydro-lH-inden-4-yl)-2-methylphenoxy)-3-methoxyacrylate

[0375] Methyl (Z)-2-(5-(2,2-dimethyl-l-oxo-2,3-dihydro-lH-inden-4-yl)-2-methylphenoxy)-3-methoxyacrylate was synthesized by following the same procedure as described in Example- 1 (step-5), using 4-bromo-2,2-dimethyl-2,3-dihydro-lH-inden-l-one and methyl (Z)-3-methoxy-2-(2-methyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenoxy)acrylate as a starting material.

[0376] ‘H-NMR (400 MHz, CDCh) 57.88 (m, 1H), 7.77-7.74 (m, 1H), 7.46-7.44 (m, 1H), 7.34 (s,lH), 7.23-7.21 (m, 1H), 7.16-7.12 (m, 1H), 6.93 (d, J = 2 Hz, 1H), 3.89 (s, 3H), 3.71 (s, 3H), 3.029 (d, J = 7.2 Hz, 2H), 2.37 (s,3H), 1.28 (s,6H); LCMS: m / z = 381.00 [M+l],

[0377] Example-3: Synthesis of methyl (Z)-3-methoxy-2-(2-methyl-5-(l,3,3-trimethyl-2-oxoindolin-6-yl)phenoxy)acrylate (Compound No. 38)

[0378]

[0379] Step-1: Synthesis of 6-bromo-l,3,3-trimethylindolin-2-one

[0380] To a stirred solution of 6-bromoindolin-2-one (1.5 g, 7.07 mmol) in tetrahydrofuran (20 mL), sodium hydride (60 %, 900 mg, 21.2 mmol) was slowly added under nitrogen atmosphere at 0 °C. The resulting reaction mixture was stirred for 20 min. To this reaction mixture, iodomethane (3.1g, 21.7 mmol), was added dropwise and the resulting mixture was stirred at 25 °C for 6 h. After completion of the reaction, the reaction mixture was quenched with dropwise addition of saturated ammonium chloride solution at 0 °C, diluted with ethyl acetate (30 mL), washed with water (2 x 30 mL) and brine (20 mL). The organic layer was dried over anhydrous sodium sulphate, filtered, and concentrated under reduced pressure to get the crude compound, which was purified by flash column chromatography to obtain 6-bromo-l,3,3-trimethylindolin-2-one (1.3 g, 5.12 mmol, 72.3 % yield) as a brown solid.

[0381] ’H-NMR (400 MHz, CDCh) 57.20-7.17 (m, 1H), 7.05 (d, J = 8 Hz, 1H), 6.97 (d, J = 2 Hz, 1H), 3.20 (s, 3H), 1.35 (s, 6H); LCMS: m / z = 255.75 [M],

[0382] Step-2: Synthesis of methyl (Z)-3-methoxy-2-(2-methyl-5-(l,3,3-trimethyl-2-oxoindolin-6-yl)phenoxy)acrylate

[0383] Methyl (Z)-3-methoxy-2-(2-methyl-5-(l,3,3-trimethyl-2-oxoindolin-6-yl)phenoxy)acrylate was synthesized by following the same procedure as described in Example 1 (step-5), using 6-bromo-l,3,3-trimethylindolin-2-one and methyl (Z)-3-methoxy-2-(2-methyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenoxy)acrylate as a starting material.

[0384] ‘H-NMR (400 MHz, CDCh) 57.39 (s, 1H), 7.26-7.21 (m, 2H), 7.18-7.11 (m, 2H), 6.94 (d, J = 1.65 Hz, 1H), 6.91 (d, J = 1.65 Hz, 1H), 3.87 (s, 3H), 3.70 (s, 3H), 3.25 (s, 3H), 2.37 (s, 3H), 1.39 (s, 6H); LCMS: m / z = 396 [M],

[0385] Example-4: Synthesis of methyl (2Z)-3-methoxy-2-(5-(3-(methoxyimino)-2,3-dihydrobenzofuran-5-yl)-2-methylphenoxy)acrylate (Compound No. 32)

[0386]

[0387] Step-1: Synthesis of 6-bromobenzofuran-3(2H)-one O-methyl oxime

[0388] To a stirred solution of 6-bromobenzofuran-3(2H)-one (300 mg, 1.41 mmol) in methanol (5 mL), O-methylhydroxylamine hydrochloride (235 mg, 2.82 mmol) was added, followed by the addition of pyridine (334 mg, 4.22 mmol) at 25 °C. The resulting reaction mixture was stirred at 60 °C for 12 h. After completion of the reaction, the reaction mixture was evaporated under reduced pressure. The residue obtained was diluted with water (10 mL) and the aqueous layer was extracted with dichloromethane (2 x 10 mL). The combined organic layers were washed with brine (20 mL) and dried over anhydrous sodium sulphate, filtered, and concentrated under reduced pressure to get the crude compound which was purified by flash column chromatography to obtain a mixture of E / Z isomers of 6-bromobenzofuran-3(2H)-one O-methyl oxime (290 mg, 1.197 mmol, 85 % yield) as yellow gum. GCMS: m / z = 242. [M], Step-2: Synthesis of methyl (2Z)-3-methoxy-2-(5-(3-(methoxyimino)-2,3-dihydrobenzofuran-5-yl)-2-methylphenoxy)acrylate

[0389] Methyl (2Z)-3-methoxy-2-(5-(3-(methoxyimino)-2,3-dihydrobenzofuran-5-yl)-2-methylphenoxy)acrylate was synthesized by following the same procedure as described in Example- 1 (step-5), using 6-bromobenzofuran-3(2H)-one O-methyl oxime and methyl (Z)-3-methoxy-2-(2-methyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenoxy)acrylate as a starting material ‘H-NMR (400 MHz, CDCh) 7.74 (d, J = 1.7 Hz, 1H), 7.49 (dd, J = 8.6, 2.0 Hz, 1H), 7.34 (d, J = 3.2 Hz, 1H), 7.20 (d, J = 8.1 Hz, 2H), 7.10 (dd, J = 7.6, 1.7 Hz, 1H), 7.00-6.96 (m, 1H), 6.87 (d, J = 1.7 Hz, 1H), 5.13 (s, 2H), 4.02 (m, 3H), 3.89 (m, 3H), 3.72 (m, 3H), 2.38 (m, 3H); LCMS: m / z = 384.00 [M+l]..

[0390] Example-5: Synthesis of methyl (Z)-2-(5-(indolin-5-yl)-2-methylphenoxy)-3-methoxyacrylate (Compound No. 13)

[0391]

[0392] Methyl (Z)-2-(5-(indolin-5-yl)-2-methylphenoxy)-3-methoxyacrylate was synthesized by following the same procedure as described in Example-1 (step-5), using 5 -bromoindoline and methyl (Z)-3-methoxy-2-(2-methyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenoxy)acrylate as a starting material

[0393] ‘H-NMR (400 MHz, CDCh) 557.56 (s, 1H), 7.17 (s, 1H), 7.14 (d, J = 7.8 Hz, 1H), 7.05 (ddd, J = 11.7, 7.9, 1.8 Hz, 2H), 6.73 (d, J = 1.5 Hz, 1H), 6.52 (d, J = 8.1 Hz, 1H), 5.60 (s, 1H), 3.86 (s, 3H), 3.64 (s, 3H), 3.43 (td, J = 8.6, 1.7 Hz, 2H), 2.93 (t, J = 8.4 Hz, 2H), 2.21 (s, 3H); LCMS: m / z = 340.25 [M+l], Example-6: Synthesis of methyl (Z)-3-methoxy-2-(2-methyl-5-(l-pivaloylindolin-5-yl)phenoxy)acrylate (Compound No. 34)

[0394]

[0395] To a stirred solution of methyl (Z)-2-(5-(indolin-5-yl)-2-methylphenoxy)-3-methoxyacrylate (80 mg, 0.23 mmol) in dicholoromethane (5 mL) trimethylacetyl chloride (0.040 mL, 0.330 mmol) and triethyl amine (0.1 mL, 0.7 mmol) was added dropwise at 0 °C and the resulting reaction mixture was stirred at 25 °C for 2 h. After completion of the reaction, the reaction mixture was evaporated under reduced pressure to obtain a crude compound, which was purified by flash column chromatography to obtain methyl (Z)-3-methoxy-2-(2-methyl-5-(l-pivaloylindolin-5-yl)phenoxy)acrylate (70 mg, 0.165 mmol, 70.1 % yield).

[0396] ’H-NMR (400 MHz, CDCh) 5 8.24 (dd, J = 8.0, 0.9 Hz, 1H), 7.35 (s, 1H), 7.34-7.32 (m, 2H), 7.20-7.18 (m, 1H), 7.11 (dd, J = 7.7, 1.7 Hz, 1H), 6.88 (d, J = 1.8 Hz, 1H), 4.29-4.25 (m, 2H), 3.87 (d, J = 9.7 Hz, 3H), 3.71 (d, J = 4.2 Hz, 3H), 3.20-3.17 (m, 2H), 2.36 (d, J = 11.3 Hz, 3H), 1.40-1.38 (m, 9H); LCMS: m / z = 424.30 [M+l],

[0397] Example-7: Synthesis of methyl (Z)-2-(5-(2,3-dihydrobenzofuran-5-yl)-2-methylphenoxy)-3-methoxyacrylate (Compound No. 3)

[0398]

[0399] A stirred solution of methyl (Z)-2-(5-bromo-2-methylphenoxy)-3-methoxyacrylate (0.4 g, 1.33 mmol) in 1,4-dioxane (10 mL) was treated in sequence with K2CO3 (0.55 g, 3.98 mmol) and (2,3-dihydrobenzofuran-5-yl)boronic acid (0.33 g, 2.0 mmol), degassed under nitrogen for 5 min., treated with tetrakis(triphenylphosphine)palladium(0) (80 mg, 0.067 mmol), and stirred for 10 min at 25 °C. The resulting reaction mixture was stirred at 90 °C for 12 h. After completion of the reaction, the reaction mixture was allowed to cool to 25 °C, passed through a Celite® pad, and washed with ethyl acetate (25 mL). The organic layer was washed with brine (20 mL), dried over anhydrous sodium sulphate, filtered, and concentrated under reduced pressure to get the crude compound, which was purified by flash column chromatography to obtain methyl (Z)-2-(5-(2,3-dihydrobenzofuran-5-yl)-2-methylphenoxy)-3-methoxyacrylate (250 mg, 0.73 mmol, 55.3 % yield).

[0400] ‘H-NMR (400 MHz, CDCh) 57.57 (s, 1H), 7.37 (d, J = 1.5 Hz, 1H), 7.23-7.18 (m, 2H), 7.08 (dd, J = 7.6, 1.7 Hz, 1H), 6.80 (d, J = 8.3 Hz, 1H), 6.77 (d, J = 1.7 Hz, 1H), 4.54 (t, J = 8.8 Hz, 2H), 3.86 (s, 3H), 3.64 (s, 3H), 3.21 (t, J = 8.8 Hz, 2H), 2.23 (s, 3H); LCMS: m / z = 340.95 [M+l],

[0401] Example-8: Synthesis of (Z)-2-(5-(2,2-dimethyl-l-oxo-2,3-dihydro-lH-inden-5-yl)-2-methylphenoxy)-3-methoxy-N-methylacrylamide (Compound No. 42)

[0402]

[0403] Step-1: Synthesis of 5-bromo-2,2-dimethyl-2,3-dihydro-lH-inden-l-one To a stirred solution of 5-bromo-2,3-dihydro-lH-inden-l-one (1.2 g, 5.69 mmol), methyl iodide (1.25 mL, 19.9 mmol) in tetrahydrofuran (15 mL), potassium tert-butoxide (1.92 g, 17.06 mmol) was added slowly at -5 °C under nitrogen atmosphere, and the resulting reaction mixture was stirred at 25 °C for 10 h. After completion of the reaction, saturated ammonium chloride solution was added dropwise followed by the addition of 20 mL ethyl acetate. The organic layer was washed with water (2 x 20 mL), saturated brine solution (20 mL), dried over anhydrous sodium sulphate, filtered and concentrated to get the crude compound 5-bromo-2,2-dimethyl-2,3-dihydro-lH-inden-l-one (0.884 g, 3.70 mmol, 65 % yield), which was used as such for the next step without further purification.

[0404] ’H-NMR (500 MHz, CHLOROFORM -D) 57.63-7.61 (m, 2H), 7.53-7.50 (m, 1H), 2.98 (s, 2H), 1.27-1.21 (m, 6H); GCMS: m / z = 240 [M +1],

[0405] Step-2: Synthesis of methyl (Z)-2-(5-(2,2-dimethyl-l-oxo-2,3-dihydro-lH-inden-5-yl)-2-methylphenoxy)-3-methoxyacrylate (Compound No. 36)

[0406]

[0407] Methyl (Z)-2-(5-(2,2-dimethyl-l-oxo-2,3-dihydro-lH-inden-5-yl)-2-methylphenoxy)-3-methoxyacrylate was synthesized by following the same procedure as described in Example- 1 (step-5), using 5-bromo-2,2-dimethyl-2,3-dihydro-lH-inden-l-one and methyl (Z)-3-methoxy-2-(2-methyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenoxy)acrylate as a starting material.

[0408] ‘H-NMR (400 MHz, CHLOROFORM-D) 5 7.79-7.75 (m, 1H), 7.52-7.48 (m, 2H), 7.37 (s, 1H), 7.24 (s, 1H), 7.17 (dd, J = 7.8, 1.7 Hz, 1H), 6.94 (d, J = 1.5 Hz, 1H), 3.90 (d, J = 8.8 Hz, 3H), 3.71 (d, J = 7.3 Hz, 3H), 3.03 (s, 2H), 2.40 (s, 3H), 1.31-1.22 (m, 6H); LCMS: m / z = 381 [M +1],

[0409] Step-3: Synthesis of (Z)-2-(5-(2,2-dimethyl-l-oxo-2,3-dihydro-lH-inden-5-yl)-2-methylphenoxy)-3-methoxy-N-methylacrylamide (Compound No. 42)

[0410] To a stirred solution of methyl (Z)-2-(5-(2,2-dimethyl-l-oxo-2,3-dihydro-lH-inden-5-yl)-2-methylphenoxy)-3-methoxyacrylate (180 mg, 0.47 mmol) in tetrahydrofuran (5 mL), methylamine in 40 % water (0.25 mL, 2.84 mmol) was added dropwise and the resulting reaction mixture was stirred at 25 °C for 12 h. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (10 mL) and washed with water (2 x 20 mL) followed by brine (10 mL), dried over anhydrous sodium sulphate, filtered, and concentrated under reduced pressure to obtain a crude compound, which was purified by flash column chromatography to obtain (Z)-2-(5-(2,2-dimethyl-l-oxo-2,3-dihydro-lH-inden-5-yl)-2-methylphenoxy)-3-methoxy-N-methylacrylamide (139 mg, 0.366 mmol, 77 % yield) as a white solid. ’H-NMR (400 MHz, DMSC,) 5 7.80-7.80 (m, 1H), 7.64-7.60 (m, 2H), 7.40-7.37 m, 1H), 7.26-7.24 (m, 1H), 7.19-7.16 (m, 1H), 6.83 (d, J = 1.0 Hz, 1H), 6.52-6.48 (m, 1H), 3.52 (s, 3H), 3.01 (s, 2H), 2.83 (d, J = 4.8 Hz, 3H), 2.29 (s, 3H), 1.44 (s, 6H); LCMS: m / z = 380.05 [M+l],

[0411] Example-9: Synthesis of methyl (2Z)-2-(5-(l-(2-acetylhydrazineylidene)-2,3-dihydro-lH-inden-4-yl)-2-methylphenoxy)-3-methoxyacrylate (Compound No. 183)

[0412]

[0413] Step-1: Synthesis of JV'-(4-bromo-2,3-dihydro-lH-inden-l-ylidene)acetohydrazide

[0414] To a stirred solution of 4-bromo-2,3-dihydro-lH-inden-l-one (0.5 g, 2.4 mmol) in ethanol (8 mL), acetohydrazide (0.193 g, 2.61 mmol)) and a catalytic amount of acetic acid (0.014 mL, 0.24 mmol) were added and the reaction mixture was heated at 70 °C for 12 h. After completion of the reaction, the reaction mixture was evaporated under reduced pressure followed by the addition of ice water. The solid obtained was filtered and dried to obtain N'-(4-bromo-2,3-dihydro-1H-inden-1-ylidene)acetohydrazide (0.54 g, 2.02 mmol, 85 % yield) as an off white solid. LCMS: m / z = 268.65 [M+l],

[0415] Step-2: Synthesis of methyl (2Z)-2-(5-(l-(2-acetylhydrazineylidene)-2,3-dihydro-lH-inden-4-yl)-2-methylphenoxy)-3-methoxyacrylate

[0416] Methyl (2Z)-2-(5-(l-(2-acetylhydrazineylidene)-2,3-dihydro-lH-inden-4-yl)-2-methylphenoxy)-3-methoxyacrylate was synthesized by following the same procedure as described in Example- 1 (step-5), using N'-(4-bromo-2,3-dihydro-1H-inden-1-ylidene)acetohydrazide and methyl (Z)-3-methoxy-2-(2-methyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenoxy)acrylate as a starting material.

[0417] ’H-NMR (400 MHz, CHLOROFORM-D) 58.20 (s, 1H), 7.73 (d, J = 6.4 Hz, 1H), 7.38-7.30 (m, 3H), 7.23 (d, J = 7.8 Hz, 1H), 7.00-6.96 (m, 1H), 6.77 (d, J = 1.5 Hz, 1H), 3.88 (d, J = 10.0 Hz, 3H), 3.71 (s, 3H), 3.13-3.10 (m, 2H), 2.69-2.66 (m, 2H), 2.40-2.38 (m, 6H); LCMS: m / z = 408 [M], Example-10: Synthesis of methyl (Z)-2-(5-(2-acetyl-l,2,3,4-tetrahydroisoquinolin-7-yl)-2-methylphenoxy)-3-methoxyacrylate (Compound No. 286)

[0418]

[0419] Step-1: Synthesis of l-(7-bromo-3,4-dihydroisoquinolin-2(lH)-yl)ethan-l-one

[0420] To a stirred solution of 7-bromo-l,2,3,4-tetrahydroisoquinoline (500 mg, 2.36 mmol) in dichloromethane (10 mL), acetic anhydride (0.45 mL, 4.71 mmol) and triethylamine (0.66 mL, 4.71 mmol) were added, and the resulting mixture was stirred at 25 °C for 12 h. After completion of the reaction, the reaction mixture was diluted with dichloromethane (5 mL), washed with saturated NaHCO₃ solution (3 x 10 mL), water (lOmL), and saturated brine solution (10 mL). The organic layer was dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to get 1-(7-bromo-3,4-dihydroisoquinolin-2(lH)-yl)ethan-l-one (455 mg, 1.792 mmol, 76% yield). LCMS: m / z = 255 [M+l],

[0421] Step-2: Synthesis of methyl (Z)-2-(5-(2-acetyl-l,2,3,4-tetrahydroisoquinolin-7-yl)-2-methylphenoxy)-3-methoxyacrylate

[0422] Methyl (Z)-2-(5-(2-acetyl-l,2,3,4-tetrahydroisoquinolin-7-yl)-2-methylphenoxy)-3-methoxyacrylate was synthesized by following the same procedure as described in Example-1 (step-5), using l-(7-bromo-3,4-dihydroisoquinolin-2(lH)-yl)ethan-l-one and methyl (Z)-3-methoxy-2-(2-methyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenoxy)acrylate as a starting material.

[0423] ’H-NMR (400 MHz, CHLOROFORM-D) 57.36 (d, J = 3.9 Hz, 1H), 7.34-7.31 (m, 1H), 7.23-7.17 (m, 3H), 7.10 (d, J = 7.8 Hz, 1H), 6.88 (s, 1H), 4.72 (d, J = 42.1 Hz, 2H), 3.89-3.83 (m, 4H), 3.70 (dd, J = 6.2, 4.8 Hz, 4H), 2.90 (dt, J = 24.7, 5.9 Hz, 2H), 2.37 (d, J = 12.5 Hz, 3H), 2.20 (d, J = 8.1 Hz, 3H); LCMS: m / z= 395.4 [M],

[0424] Example-11: Synthesis of methyl (2Z)-3-methoxy-2-(5-(l'-(methoxyimino)-l',3'-dihydrospiro[cyclopropane-l,2'-inden]-5'-yl)-2-methylphenoxy)acrylate (Compound No. 78)

[0425]

[0426] Step-1: Synthesis of 5'-bromospiro[cyclopropane-l,2'-inden]-l'(3'H)-one

[0427] To a stirred solution of 5-bromo-2,3-dihydro-lH-inden-l-one (1.5 g, 7.11 mmol) in tetrahydrofuran (5 mL), 1,2-dibromoethane (0.74 mL, 8.53 mmol) and sodium hydride (0.99 g, 24.87 mmol) were added slowly at 0 °C under nitrogen atmosphere. The resulting reaction mixture was warmed to 25 °C and stirred further at the same temperature for 16 h. After completion of the reaction, saturated ammonium chloride solution was added dropwise followed by the addition of 20 mL of ethyl acetate, washed with water (3 x 30 mL) and saturated brine solution (3 x 30 mL). The organic layer was dried over anhydrous sodium sulphate, filtered and concentrated to obtain a crude product, which was purified by flash column chromatography to obtain 5'-bromospiro[cyclopropane-l,2'-inden]-r(3'H)-one (0.354 g, 1.492 mmol, 21 % yield) as a brown gum. ’H-NMR (400 MHz, CHLOROFORM-D) 5 7.67 (t, J = 0.9 Hz, 1H), 7.65-7.63 (m, 1H), 7.55-7.52 (m, 1H), 3.21 (s, 2H), 1.48-1.45 (m, 2H), 1.18-1.14 (m, 2H); LCMS: m / z = 237 [M],

[0428] Step-2: Synthesis of 5'-bromospiro[cyclopropane-l,2'-inden]-l'(3'H)-one O-methyl oxime To a stirred solution of 5'-bromospiro[cyclopropane-l,2'-inden]-r(3'H)-one (354 mg, 1.49 mmol) in tetrahydrofuran (5 mL), O-methylhydroxylamine hydrochloride (249 mg, 2.99 mmol) was slowly added, and the resulting mixture was stirred at 25 °C for 15 h. After completion of the reaction, the reaction mixture was evaporated under reduced pressure, diluted with water (10 mL) and extracted with dichloromethane (20 mL). The organic layer was washed with brine solution (10 mL), dried over anhydrous sodium sulphate, filtered and evaporated under reduced pressure to obtain a crude compound, which was purified by flash column chromatography to obtain 5'-bromospiro[cyclopropane-l,2'-inden]-r(3'H)-one O-methyl oxime (238 mg, 0.894 mmol, 59.9 % yield) as a brown solid. ’H-NMR(400 MHz, CHLOROFORM-D) 58.18 (d, J = 8.3 Hz, 1H), 7.47 (s, 1H), 7.42-7.36 (m, 1H), 3.92-3.79 (m, 3H), 3.12-3.02 (m, 2H), 1.28-1.15 (m, 2H), 0.92 (ddd, J = 23.7, 6.7, 3.9 Hz, 2H); LCMS: m / z = 267.75 [M+l],

[0429] Step-3: Synthesis of methyl (2Z)-3-methoxy-2-(5-(l'-(methoxyimino)-l',3'-dihydrospiro[cyclopropane-l,2'-inden]-5'-yl)-2-methylphenoxy)acrylate

[0430] Methyl (2Z)-3-methoxy-2-(5-(r-(methoxyimino)-r,3'-dihydrospiro[cyclopropane-l,2'-inden]-5'-yl)- 2-methylphenoxy)acrylate was synthesized by following the same procedure as described in Example-1 (step-5), using 5'-bromospiro[cyclopropane-l,2'-inden]-r(3'H)-one O-methyl oxime and methyl (Z)- 3 -methoxy-2-(2-methyl-5 -(4,4,5,5 -tetramethyl- 1,3,2-dioxaborolan-2-yl)phenoxy)acrylate as a starting material. ‘H-NMR (500 MHz, CHLOROFORM-D) 58.34 (d, J = 7.9 Hz, 1H), 7.44 (d, J = 0.8 Hz, 1H), 7.42 (d, J = 1.8 Hz, 1H), 7.35 (s, 1H), 7.24-7.22 (m, 1H), 7.16 (dd, J = 7.7, 1.7 Hz, 1H), 6.93 (d, J = 1.7 Hz, 1H), 3.95 (s, 3H), 3.88 (d, J = 1.3 Hz, 3H), 3.72 (s, 3H), 3.16 (s, 2H), 2.39 (d, J = 2.7 Hz, 3H), 1.27-1.26 (m, 2H), 0.99-0.97 (m, 2H); LCMS: m / z = 408.2 [M+l],

[0431] Example-12: Synthesis of methyl (Z)-2-(5-(4-hydroxy-4-methylchroman-6-yl)-2-methylphenoxy)-3-methoxyacrylate (Compound No. 281)

[0432]

[0433] Step-1: Synthesis of 6-bromo-4-methylchroman-4-ol To a stirred solution of 6-bromochroman-4-one (500 mg, 2.20 mmol) in tetrahydrofuran (5 mL), methyl magnesium chloride (1.5 mL, 4.40 mmol) was added dropwise at 0 °C, and the resulting mixture was stirred at 0 °C - 25 °C for 12 h. After completion of the reaction, the reaction mixture was quenched with saturated ammonium chloride solution and extracted with ethyl acetate (3 x 10 mL). The combined organic layers were washed with brine solution (20 mL), dried over anhydrous sodium sulphate, filtered and evaporated under reduced pressure to obtain a crude compound which was purified by flash column chromatography to obtain 6-bromo-4-methylchroman-4-ol (294 mg, 1.211 mmol, 55 % yield) as a brown gum; GCMS: m / z = 244 [M+1],

[0434] Step-2: Synthesis of methyl (Z)-2-(5-(4-hydroxy-4-methylchroman-6-yl)-2-methylphenoxy)-3-methoxyacrylate

[0435] Methyl (Z)-2-(5-(4-hydroxy-4-methylchroman-6-yl)-2-methylphenoxy)-3-methoxyacrylate was synthesized by following the same procedure as described in Example- 1 (step-5), using 6-bromo-4-methylchroman-4-ol and methyl (Z)-3-methoxy-2-(2-methyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenoxy)acrylate as a starting material. ’H-NMR (400 MHz, CHLOROFORM-D) 5 7.62 (d, J = 2.4 Hz, 1H), 7.34 (s, 1H), 7.31 (dd, J = 8.6, 2.2 Hz, 1H), 7.21-7.19 (m, 1H), 7.08 (dd, J = 7.7, 1.8 Hz, 1H), 6.87-6.85 (m, 2H), 4.35-4.23 (m, 2H), 3.90-3.87 (m, 3H), 3.72 (t, J = 3.2 Hz, 3H), 2.38 (s, 3H), 2.14-2.07 (m, 2H), 1.90 (d, J = 2.2 Hz, 1H), 1.67 (s, 3H); LCMS: m / z = 385.95 [M+1], Example 13: Synthesis of methyl (Z)-2-(5-(4-acetoxy-4-methylchroman-6-yl)-2-methylphenoxy)-3-methoxyacrylate (Compound No. 282)

[0436]

[0437] To a stirred solution of methyl (Z)-2-(5-(4-hydroxy-4-methylchroman-6-yl)-2-methylphenoxy)-3-methoxyacrylate (200 mg, 0.52 mmol) and triethylamine (0.15 mL, 1.041 mmol) in dichloromethane (5 mL), acetic anhydride (0.1 mL, 1.041 mmol) was added dropwise at 0 °C, and the resulting reaction mixture was stirred at 25 °C for 16 h. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (15 mL), washed with water (10 mL), saturated NaHCO₃ solution (2 x 10 mL), and brine solution (10 mL). The organic layer was dried over anhydrous sodium sulphate, filtered and concentrated to obtain a crude compound which was purified by flash column chromatography to obtain methyl (Z)-2-(5-(4-acetoxy-4-methylchroman-6-yl)-2-methylphenoxy)-3-methoxyacrylate (119 mg, 0.279 mmol, 53.6 % yield) as a pale-yellow gum. ’H-NMR (400 MHz, CHLOROFORM-D) 57.62 (d, J = 2.4 Hz, 1H), 7.34 (s, 1H), 7.31 (dd, J = 8.6, 2.4 Hz, 1H), 7.20 (d, J = 8.1 Hz, 1H), 7.08 (dd, J = 7.8, 1.7 Hz, 1H), 6.87-6.85 (m, 2H), 4.35-4.23 (m, 2H), 3.88 (s, 3H), 3.70 (d, J = 4.6 Hz, 3H), 2.38 (s, 3H), 2.12-2.09 (m, 2H), 1.67 (s, 3H), 1.55 (s, 3H); LCMS: m / z = 426 [M],

[0438] Example 14: Synthesis of methyl (Z)-3-methoxy-2-(2-methyl-5-(8-oxo-5, 6,7,8-tetrahydronaphthalen-2-yl)phenoxy)acrylate (Compound No.28)

[0439]

[0440] Methyl (Z)-3-methoxy-2-(2-methyl-5-(8-oxo-5,6,7,8-tetrahydronaphthalen-2-yl)phenoxy)acrylate was synthesized by following the same procedure as described in Example-1 (step-5), using 7-bromo-3,4-dihydronaphthalen-l(2H)-one and methyl (Z)-3-methoxy-2-(2-methyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenoxy)acrylate as a starting material. ’H-NMR (400 MHz, CHLOROFORM-D) 5 8.19 (d, J = 2.0 Hz, 1H), 7.63 (dd, J = 7.8, 2.2 Hz, 1H), 7.35 (s, 1H), 7.30 (d, J = 7.8 Hz, 1H), 7.22 (d, J = 7.8 Hz, 1H), 7.16 (dd, J = 7.8, 1.7 Hz, 1H), 6.93 (d, J = 1.5 Hz, 1H), 3.90-3.85 (m, 3H), 3.69 (d, J = 19.8 Hz, 3H), 2.99 (t, J = 6.1 Hz, 2H), 2.68 (t, J = 6.5 Hz, 2H), 2.40 (d, J = 11.7 Hz, 3H), 2.19-2.13 (m, 2H); LCMS: m / z = 384.15 [M+18],

[0441] Example 15: Synthesis of methyl (2Z)-2-(5-(8-(((cyclopropanecarbonyl)oxy)imino)-5,6,7,8-tetrahydronaphthalen-2-yl)-2-methylphenoxy)-3-methoxyacrylate (Compound No. 115)

[0442]

[0443] Step-1: Synthesis of methyl (2Z)-2-(5-(8-(hydroxyimino)-5,6,7,8-tetrahydronaphthalen-2-yl)-2-methylphenoxy)-3-methoxyacrylate (Compound No.90)

[0444]

[0445] To a stirred solution of methyl (Z)-3-methoxy-2-(2-methyl-5-(8-oxo-5,6,7,8-tetrahydronaphthalen-2-yl)phenoxy)acrylate (1g, 2.73 mmol) (Example 14) in MeOH (8 mL), hydroxylamine hydrochloride (0.284 g, 4.09 mmol) and pyridine (0.25 mL, 3.00 mmol) were added, and the resulting reaction mixture was stirred at 25 °C for 15 h. After completion of the reaction, the reaction mixture was evaporated under reduced pressure, diluted with water (10 mL) and extracted with dichloromethane (20 mL). The organic layer was washed with brine solution (10 mL), dried over anhydrous sodium sulphate, filtered and evaporated under reduced pressure to obtain a crude compound, which was purified by flash column chromatography to obtain methyl (2Z)-2-(5-(8-(hydroxyimino)-5,6,7,8-tetrahydronaphthalen-2-yl)-2-methylphenoxy)-3-methoxyacrylate (790 mg, 2.071 mmol, 76 % yield) as an off-white solid. ’H-NMR (400 MHz, CHLOROFORM-D) 58.07 (d, J = 2.0 Hz, 1H), 7.40 (dd, J = 7.8, 2.0 Hz, 1H), 7.34 (s, 1H), 7.19 (t, J = 7.0 Hz, 2H), 7.15 (dd, J = 7.7, 1.6 Hz, 1H), 6.92 (d, J = 1.7 Hz, 1H), 3.88 (s, 3H), 3.71 (s, 3H), 2.84-2.77 (m, 4H), 2.38 (s, 3H), 1.89 (t, J = 6.1 Hz, 2H); LCMS: m / z = 382 [M+1],

[0446] Step-2: Synthesis of methyl (2Z)-2-(5-(8-(((cyclopropanecarbonyl)oxy)imino)-5, 6,7,8-tetrahydronaphthalen-2-yl)-2-methylphenoxy)-3-methoxyacrylate (Compound No. 115)

[0447] To a stirred solution of methyl (2Z)-2-(5-(8-(hydroxyimino)-5,6,7,8-tetrahydronaphthalen-2-yl)-2-methylphenoxy)-3-methoxyacrylate (286 mg, 0.750 mmol) and triethylamine (0.21 mL, 1.5 mmol) in dichloromethane (5 mL), cyclopropanecarbonyl chloride (118 mg, 1.13 mmol) was added slowly at 0 °C, and the resulting reaction mixture was stirred at 25 °C for 2 h. After completion of the reaction, the reaction mixture was evaporated under reduced pressure to obtain a crude compound, which was purified by flash column chromatography to obtain methyl (2Z)-2-(5-(8-(((cyclopropanecarbonyl)oxy)imino)-5,6,7,8-tetrahydronaphthalen-2-yl)-2-methylphenoxy)-3-methoxyacrylate (91 mg, 0.202 mmol, 27.0 % yield) as a brown solid. Tf-NMR (400 MHz, CHLOROFORM-D) 5 8.28 (d, J = 2.0 Hz, 1H), 7.47 (dd, J = 8.1, 2.0 Hz, 1H), 7.34 (s, 1H), 7.22 (s, 1H), 7.19 (d, J = 6.1 Hz, 1H), 7.15 (dd, J = 7.7, 1.6 Hz, 1H), 6.92 (d, J = 1.5 Hz, 1H), 3.90 (s, 3H), 3.70 (s, 3H), 2.92 (t, J = 6.6 Hz, 2H), 2.81 (t, J = 6.1 Hz, 2H), 2.38 (s, 3H), 1.92 (t, J = 6.1 Hz, 2H), 1.25 (t, J = 7.1 Hz, 1H), 1.17-1.09 (m, 2H), 1.00-0.96 (m, 2H); LCMS: m / z = 450.2 [M+1],

[0448] Example 16: Synthesis of methyl (2Z)-2-(5-(8-((cyclopropylmethoxy)imino)-5, 6,7,8-tetrahydronaphthalen-2-yl)-2-methylphenoxy)-3-methoxyacrylate (Compound No. 142)

[0449]

[0450] To a stirred solution of methyl (Z)-3-methoxy-2-(2-methyl-5-(8-oxo-5,6,7,8-tetrahydronaphthalen-2-yl)phenoxy)acrylate (300 mg, 0.82 mmol) (Example 14) in tetrahydrofuran (5 mL), O- (cyclopropylmethyl)hydroxylamine hydrochloride (132 mg, 1.06 mmol) was added and the resulting mixture was stirred at 25 °C for 15 h. After completion of the reaction, the reaction mixture was evaporated under reduced pressure, diluted with water (10 mL) and extracted with dichloromethane (20 mL). The organic layer was washed with brine solution (10 mL), dried over anhydrous sodium sulphate, filtered and evaporated under reduced pressure to obtain a crude compound which was purified by flash column chromatography to obtain methyl (2Z)-2-(5-(8-((cyclopropylmethoxy)imino)-5, 6,7,8-tetrahydronaphthalen-2-yl)-2-methylphenoxy)-3-methoxyacrylate (145 mg, 0.333 mmol, 40.7 % yield) as an off white solid. ’H-NMR (400 MHz, CHLOROFORM-D) 5 8.13 (d, J = 1.7 Hz, 1H), 7.38 (dd, J = 7.9, 2.1 Hz, 1H), 7.33 (s, 1H), 7.22-7.16 (m, 2H), 7.15-7.13 (m, 1H), 6.93 (d, J = 1.7 Hz, 1H), 4.00 (d, J = 7.1 Hz, 2H), 3.88 (s, 3H), 3.71 (s, 3H), 2.81-2.75 (m, 4H), 2.37 (d, J = 10.5 Hz, 3H), 1.90-1.84 (m, 2H), 1.43 (s, 3H), 1.26-1.19 (m, 1H), 0.59-0.54 (m, 2H), 0.35-0.31 (m, 2H); LCMS: m / z = 436.15 [M+1],

[0451] Example 17: Synthesis of methyl (Z)-2-(5-(l,3-dioxo-2-propylisoindolin-5-yl)-2-methylphenoxy)-3-methoxyacrylate (Compound No. 244)

[0452]

[0453] Step-1: Synthesis of 5-bromo-2-propylisoindoline-l, 3-dione

[0454] To a stirred solution of 5 -bromoisoindoline- 1, 3-dione (1 g, 4.42 mmol), 1 -iodopropane (1.13 g, 6.64 mmol) in N,N-dimethylformamide (10 mL), sodium hydride (0.177 g, 4.42 mmol) was added slowly, and the resulting mixture was stirred at 25 °C for 16 h. After completion of the reaction, the reaction mixture was diluted with water (20 mL) and the precipitate was filtered, washed with water and recrystallized in ethyl acetate / hexane to obtain 5-bromo-2-propylisoindoline-l, 3-dione (840 mg, 3.13 mmol, 70.8 % yield) as a white solid. LCMS: m / z = 371.80 [M+1],

[0455] Step-2: Synthesis of methyl (Z)-2-(5-(l,3-dioxo-2-propylisoindolin-5-yl)-2-methylphenoxy)-3-methoxyacrylate

[0456] Methyl (Z)-2-(5-(l,3-dioxo-2-propylisoindolin-5-yl)-2-methylphenoxy)-3-methoxyacrylate was synthesized by following the same procedure as described in Example-1 (step-5), using 5-bromo-2-propylisoindoline-1, 3-dione and methyl (Z)-3-methoxy-2-(2-methyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenoxy)acrylate as a starting material. ’H-NMR (400 MHz, CHLOROFORM-D) 5 7.96 (t, J = 0.7 Hz, 1H), 7.85 (d, J = 7.8 Hz, 1H), 7.82 (dd, J = 7.6, 1.5 Hz, 1H), 7.38 (s, 1H), 7.28 (d, J = 8.1 Hz, 1H), 7.19 (dd, J = 7.8, 1.7 Hz, 1H), 6.94 (d, J = 1.7 Hz, 1H), 3.91 (s, 3H), 3.73 (s, 3H), 3.67 (t, J = 7.3 Hz, 2H), 2.41 (s, 3H), 1.72 (td, J = 14.7, 7.4 Hz, 2H), 0.96 (t, J = 7.5 Hz, 3H); LCMS: m / z = 409 [M],

[0457] Example 18: Synthesis of methyl (Z)-2-(5-(3,3-difluoro-l-methyl-2-oxoindolin-5-yl)-2-methylphenoxy)-3-methoxyacrylate (Compound No. 180)

[0458]

[0459] Step-1: Synthesis of 5-bromo-3,3-difluoro-l-methylindolin-2-one

[0460] To a stirred solution of 5-bromo-l-methylindoline-2, 3-dione (600 mg, 2.5 mmol) in dichloromethane (10 ml), diethylaminosulfur trifluoride (DAST) (0.83 mL, 6.25 mmol) was added at 0 °C under nitrogen atmosphere. The resulting reaction mixture was stirred at 25 °C for 16 h. After completion of the reaction, the reaction mixture was concentrated and diluted with water (10 mL) to obtain a solid. The solid was filtered, washed with hexane (20 mL) and dried to obtain 5-bromo-3,3-difluoro-l-methylindolin-2-one (420 mg, 1.6 mmol, 64.1 %yield) as an off white solid. GCMS: m / z = 263 [M+l], Step-2: Synthesis of methyl (Z)-2-(5-(3,3-difluoro-l-methyl-2-oxoindolin-5-yl)-2-methylphenoxy)-3-methoxyacrylate

[0461] Methyl (Z)-2-(5 -(3,3 -difluoro- 1 -methyl -2 -oxoindolin-5 -yl)-2-methylphenoxy)-3 -methoxyacrylate was synthesized by following the same procedure as described in Example-1 (step-5), using 5-bromo-3,3-difluoro-l-methylindolin-2-one and methyl (Z)-3-methoxy-2-(2-methyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenoxy)acrylate as a starting material. ’H-NMR (500 MHz, CHLOROFORM-D) 5 7.68-7.67 (m, 1H), 7.63-7.61 (m, 1H), 7.37 (s, 1H), 7.23 (dd, J = 7.7, 0.5 Hz, 1H), 7.09 (dd, J = 7.6, 1.7 Hz, 1H), 6.93 (d, J = 8.2 Hz, 1H), 6.85 (d, J = 1.8 Hz, 1H), 3.90 (s, 3H), 3.73 (s, 3H), 3.25 (s, 3H), 2.39 (s, 3H); LCMS: m / z = 404 [M+1],

[0462] Example 19: Synthesis of methyl (2Z)-2-(5-(3-(isopropoxyimino)-l-methyl-2-oxoindolin-5-yl)-2-methylphenoxy)-3-methoxyacrylate (Compound No. 111)

[0463]

[0464] Step-1: Synthesis of 5-bromo-3-(isopropoxyimino)-l-methylindolin-2-one To a stirred solution of 5-bromo-l-methylindoline-2, 3-dione (600 mg, 2.5 mmol), and O-isopropylhydroxylamine hydrochloride (307 mg, 2.75 mmol) in methanol (5 mL), potassium phosphate dibasic (435 mg, 2.5 mmol) was added at 25 °C under nitrogen atmosphere. The resulting reaction mixture was stirred at 25 °C for 12 h. After completion of the reaction, the reaction mixture was concentrated and diluted with water to obtain a solid. The solid was filtered, washed (10 mL) with hexane (5 mL) and dried to obtain 5-bromo-3-(isopropoxyimino)-l-methylindolin-2-one (680 mg, 2.288 mmol, 92 % yield) as a yellow solid. ’H-NMR (400 MHz, CHLOROFORM-D) 58.06 (d, J = 2.0 Hz, 1H), 7.51 (dd, J = 8.2, 2.1 Hz, 1H), 6.73-6.69 (m, 1H), 4.83-4.77 (m, 1H), 3.25-3.20 (m, 3H), 1.46-1.42 (m, 6H); GCMS: m / z = 298 [M +1],

[0465] Step-2: Synthesis of methyl (2Z)-2-(5-(3-(isopropoxyimino)-l-methyl-2-oxoindolin-5-yl)-2-methylphenoxy)-3-methoxyacrylate.

[0466] Methyl (2Z)-2-(5-(3-(isopropoxyimino)-l-methyl-2-oxoindolin-5-yl)-2-methylphenoxy)-3-methoxyacrylate was synthesized by following the same procedure as described in Example- 1 (step-5), using 5-bromo-3-(isopropoxyimino)-l-methylindolin-2-one and methyl (Z)-3-methoxy-2-(2-methyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenoxy)acrylate as a starting material. ’H-NMR (400 MHz, CHLOROFORM-D) 58.13 (d, J = 1.7 Hz, 1H), 7.52 (dd, J = 8.1, 2.0 Hz, 1H), 7.34 (s, 1H), 7.23 (d, J = 8.3 Hz, 1H), 7.10 (dd, J = 7.6, 1.7 Hz, 1H), 6.88 (d, J = 1.7 Hz, 1H), 6.86 (d, J = 8.1 Hz, 1H), 4.83-4.76 (m, 1H), 3.88 (d, J = 5.9 Hz, 3H), 3.72 (d, J = 4.6 Hz, 3H), 3.27 (s, 3H), 2.39 (s, 3H), 1.44 (d, J = 6.1 Hz, 6H); LCMS: m / z = 439 [M+1],

[0467] Accordingly, the compounds of the present invention have been illustrated in the following Table 1, in a non-limiting manner. In the following examples, M+l (or M-l) means the molecular ion peak, plus or minus 1 a.m.u. (atomic mass unit) respectively, as observed in the mass spectrometry. Similarly, M+18 peaks may indicate adducts such as water addition.

[0468] All1H NMR experiments were reported in units, parts per million (ppm), and were measured relative to the signals for residual deuterated solvents as the internal standard unless otherwise stated.

[0469] The following compounds (Table 1) of the present invention were obtained using analogous procedures as described in the schemes or the examples.

[0470] Table: 1

[0471]

[0472]

[0473]

[0474]

[0475]

[0476]

[0477]

[0478]

[0479]

[0480]

[0481]

[0482]

[0483]

[0484]

[0485]

[0486]

[0487]

[0488]

[0489]

[0490]

[0491]

[0492]

[0493]

[0494]

[0495]

[0496]

[0497]

[0498]

[0499]

[0500]

[0501]

[0502]

[0503]

[0504]

[0505]

[0506]

[0507]

[0508]

[0509]

[0510]

[0511] BIOLOGY EXAMPLES:

[0512] As described herein, the compounds of formula (I) show fungicidal activities which are exerted with respect to numerous phytopathogenic fungi which attack on important agricultural crops. The compounds of the present invention were assessed for their activity as described in the following tests:

[0513] In vitro experiments:

[0514] Example 1: Pyricularia oryzae (Rice blast):

[0515] The compounds were dissolved in 0.3% dimethyl sulfoxide and then added to potato dextrose agar medium just prior to dispensing it into petri dishes. 5 mL medium, with the compound in the desired test concentration, was dispensed into a 60 mm sterile petri -plate. After solidification, each plate was seeded with a 5 mm size mycelial disc taken from the periphery of an actively growing virulent culture plate of Pyricularia oryzae. The plates were incubated in growth chambers at 25 °C temperature and 60% relative humidity for seven days and the radial growth was measured and compared to the one of the untreated inoculated control. Compounds 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 13, 16, 17, 18, 19, 20, 21, 26, 27, 33, 36, 37, 41, 44, 45, 47, 48, 49, 50, 51, 52, 54, 55, 56, 57, 58, 59, 60, 63, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 80, 85, 88, 89, 90, 95, 97, 98, 106, 107, 113, 114, 115, 116, 118, 119, 125, 126, 127, 130, 131, 132, 133, 134, 135, 136, 137, 139, 140, 142, 143, 147, 148, 150, 151, 154, 157, 161, 162, 163, 164, 174, 175, 176, 177, 184, 185, 186, 188, 190, 192, 193, 194, 195, 196, 198, 199, 204, 208, 214, 222, 223, 227, 228, 229, 230, 231, 233, 234, 237, 238, 239, 240, 241, 242, 254, 255, 257, 258, 259, 260, 267, 268, 269, 271, 274, 278, 279, 281, 282, 283, 284 and 285 at 300 ppm gave more than or equal to 70 % control in these tests when compared to the untreated check which showed extensive pathogen growth.

[0516] Example 2: Alternaria solani (early blight of tomato / potato):

[0517] The compounds were dissolved in 0.3% dimethyl sulfoxide and then added to potato dextrose agar medium just prior to dispensing it into petri dishes. 5 mL medium, with the compound in the desired concentration, was dispensed into a 60 mm sterile petri-plate. After solidification, each plate was seeded with a 5 mm size mycelial disc taken from the periphery of an actively growing virulent culture plate of Alternaria solani. The plates were incubated in growth chambers at 25 °C temperature and 60% relative humidity for seven days and the radial growth was measured and compared to the one of the untreated inoculated control.

[0518] Compounds 1, 4, 8, 20, 21, 30, 49, 74, 80, 97, 113, 114, 118, 119, 122, 131, 132, 141, 151, 174, 184, 186, 190, 191, 194, 216, 227, 228, 238, 241, 249, 255, 260, 282 and 285 at 300 ppm gave more than or equal to 70 % control in these tests when compared to the untreated check which showed extensive pathogen growth.

[0519] Example 3: Colletotrichum capsici (anthracnose):

[0520] The compounds were dissolved in 0.3% dimethyl sulfoxide and then added to potato dextrose agar medium just prior to dispensing it into petri dishes. 5 mL medium, with the compound in the desired concentration, was dispensed into a 60 mm sterile petri-plate. After solidification, each plate was seeded with a 5 mm size mycelial disc taken from the periphery of an actively growing virulent culture plate of Colletotrichum capsici. The plates were incubated in growth chambers at 25 °C temperature and 60% relative humidity for seven days and the radial growth was measured and compared to the one of the untreated inoculated control.

[0521] Compound 4, 7, 8, 90 and 282 at 300 ppm gave more than or equal to 70% control in these tests when compared to the untreated check which showed extensive pathogen growth.

[0522] Example 4: Phytophthora infestans (Late blight of potato & tomato):

[0523] The compounds were dissolved in 0.3% dimethyl sulfoxide and then added to Rye Agar medium just prior to dispensing it into petri dishes. 5 mL medium, with the compound in the desired test concentration, was dispensed into a 60 mm sterile petri-plate. After solidification, each plate was seeded with a 5 mm size mycelial disc taken from the periphery of an actively growing virulent culture plate of Phytophthora infestans. The plates were incubated in growth chambers at 18 °C temperature and 95% relative humidity for seven days and the radial growth was measured and compared to the one of the untreated inoculated control.

[0524] Compounds 1, 2, 3, 4, 6, 7, 8, 9, 10, 11, 12, 13, 15, 16, 20, 21, 22, 23, 24, 26, 27, 28, 30, 31, 32, 36, 37, 38, 39, 41, 45, 49, 54, 55, 59, 65, 67, 76, 78, 81, 90, 91, 92, 113, 114, 115, 116, 118, 119, 120, 121, 122, 126, 129, 130, 131, 132, 133, 134, 139, 147, 148, 150, 151, 154, 155, 156, 157, 165, 167, 168, 171, 174, 175, 184, 186, 187, 194, 207, 228, 238, 241, 256, 257, 258, 259, 260, 268, 270, 271, 272, 273, 274, 280, 281, 282, 283 and 285 at 300 ppm gave more than or equal to 70% control in these tests when compared to the untreated check which showed extensive pathogen growth.

[0525] Example 5: Botrytis cinerea (Gray mold):

[0526] Yeast, bacterial peptone and sodium acetate (YBA) liquid medium containing a BOTRCI (104spores / mL) spore suspension was prepared. For the inhibition assay, each test compound was solved in dimethyl sulfoxide and 100 μl of the respective test solution was given into a well of a 96-well microtiter plate, consequently, the same volume (100 μl) of the media and spore suspension was added to each well to obtain the final test concentration. The plates were incubated at 22 °C for 15-18 days. The growth inhibition was evaluated by measuring the OD600. Percent inhibition was calculated with the below formula:

[0527] 1= (C-B)-(T-B) / (C-B)*100

[0528] Where T=treatment, C=control, and B=blank

[0529] Compounds 4, 6, 7, 9, 11, 12, 13, 17, 20, 21, 22, 23, 24, 25, 26, 27, 31, 36, 38, 40, 41, 45, 46, 47, 49, 52, 54, 55, 56, 57, 59, 69, 70, 75, 76, 77, 78, 79, 80, 81, 83, 89, 90, 91, 95, 96, 97, 104, 105, 106, 109, 110, 114, 116, 118, 119, 120, 121, 122, 131, 133, 134, 137, 139, 140, 142, 143, 148, 149, 150, 151, 154, 156, 157, 165, 168, 169, 174, 175, 176, 184, 189, 190, 191, 192, 194, 199, 207, 215, 216, 228, 229, 231, 237, 238, 239, 241, 242, 243, 250, 260, 262, 268, 269, 270, 271, 272, 273, 274, 278, 280 and 281 at 300 ppm gave more than or equal to 70 % control in these tests when compared to the untreated inoculated check which showed extensive pathogen growth.

[0530] Example 6: Sclerotinia sclerotiorum (White mold):

[0531] The compounds were dissolved in 0.3% dimethyl sulfoxide and then added to potato dextrose agar medium just prior to dispensing it into petri dishes. 5 mL medium with the compound in the desired test concentration was dispensed into 60 mm sterile petri-plates. After solidification, each plate was seeded with a 5 mm size mycelial disc taken from the periphery of an actively growing virulent culture plate. The plates were incubated in growth chambers at 20 °C temperature and 70% relative humidity for seven days and the radial growth was measured and compared to the one of the inoculated, untreated control. Compound 10, 30, 42, 48, 59, 127, 133, 134, 270, 281, 282, 283 and 284 at 300 ppm gave more than or equal to 70 % control in these tests when compared to the untreated check which showed extensive pathogen growth.

[0532] Example 7: Septoria nodorum (Leaf blotch)

[0533] Yeast, bacterial peptone and sodium acetate (YBA) liquid medium containing a Septoria nodorum (104spores / mL) spore suspension was prepared. For the inhibition assay, each test compound was dissolved in dimethyl sulfoxide and 100 pL of the respective test solution was dispensed into a 96-well microtiter plate, consequently, the same volume (100 pL) of the media and spore suspension were added to each well to obtain the final test concentration. The plates were incubated at 22 °C for 15-18 days. The growth inhibition was evaluated by measuring the OD600. Percent inhibition was calculated with the below formula:

[0534] 1= (C-B)-(T-B) / (C-B)*100

[0535] Where T=treatment, C=control, and B=blank.

[0536] Compounds 1, 2, 3, 5, 6, 7, 20, 21, 22, 23, 24, 25, 26, 27, 28, 31, 35, 36, 38, 39, 41, 45, 48, 49, 52, 59, 69, 70, 72, 82, 83, 89, 90, 91, 92, 106, 114, 119, 126, 129, 131, 133, 134, 136, 148, 151, 154, 156, 157, 158, 160, 161, 162, 164, 166, 174, 175, 178, 180, 184, 186, 191, 192, 204, 211, 215, 228, 241, 242, 246, 249, 250, 251, 252, 253, 254, 255, 266, 267, 268, 269, 271, 272, 273, 274, 276, 277, 278 and 281at 300 ppm gave more than or equal to 70% control in these tests when compared to the untreated check which showed extensive disease development.

[0537] Example 8: Rhizoctonia solani (Rice sheath blight / Potato black scurf):

[0538] Compounds were dissolved in 0.3 % dimethyl sulfoxide and then added to potato dextrose agar medium just prior to dispensing it into petri dishes. 5 mL medium with a compound in the desired test concentration was dispensed into 60 mm sterile petri-plates. After solidification each plate was seeded with a 5 mm size mycelial disc taken from the periphery of an actively growing virulent culture plate. Plates were incubated in growth chambers at 25 °C temperature and 60 % relative humidity for seven days and the radial growth was measured and compared to that of the untreated control.

[0539] Compound 48 at 300 ppm gave more than or equal to 70 % control in these tests when compared to that of the untreated control which showed extensive pathogen growth.

[0540] Example 9: Fusarium culmorum (Foot rot / Head blight of cereals):

[0541] The compounds were dissolved in 0.3 % dimethyl sulfoxide and then added to Potato Dextrose Agar medium just prior to dispensing it into petri dishes. 5 mL medium, with compound in the desired concentration, was dispensed into 60 mm sterile petri-plates. After solidification, each plate was seeded with a 5 mm size mycelial disc taken from the periphery of an actively growing virulent culture plates of Fusarium culmorum. The plates were incubated in growth chambers at 25 °C temperature and 60 % relative humidity for seven days, and the radial growth was measured and compared to that of the untreated control.

[0542] Compound 48 and 131 at 300 ppm gave more than or equal to 70 % control in these tests when compared to that of the untreated control which showed extensive pathogen growth.

[0543] Green House tests on plant:

[0544] Example A: Phakopsora pachyrhizi test on Soybean plants

[0545] The compounds were dissolved in 2% dimethyl sulfoxide / acetone and then mixed with water containing emulsifier to the calibrated spray volume of 30 mL. Each spray solution was poured into a spray bottle for further application.

[0546] To test the preventive activity of the compound, healthy young soybean plants, raised in the greenhouse, were sprayed with the active compound preparation at the stated application rates inside the spray cabinets using hollow cone nozzles. One day after treatment, the plants were inoculated with a conidial suspension containing 2 x105Phakopsora pachyrhizi inoculum. The inoculated plants were then kept in a greenhouse chamber at 22-24 °C temperature and 80-90% relative humidity for disease expression. A visual assessment of the compound’s performance was carried out by rating the disease severity (0-100% scale) on treated plants 3, 7, 10 and 15 days after application. The efficacy (% control) of the compound was calculated by comparing the disease rating in the treatment with the one of the untreated control. The treated plants were also assessed for plant damage by recording symptoms like necrosis, chlorosis and stunting.

[0547] Compounds 1, 3, 4, 5, 6, 7, 8, 15, 16, 17, 18, 19, 20, 21, 23, 24, 25, 26, 30, 33, 36, 37, 38, 41, 46, 47, 49, 55, 56, 64, 65, 66, 67, 74, 81, 88, 89, 91, 95, 96, 97, 102, 103, 105, 107, 114, 115, 116, 129, 130, 131, 132, 139, 147, 149, 158, 160, 162, 164, 170, 174, 175, 176, 178, 180, 183, 184, 186, 188, 194, 195, 198, 199, 200, 208, 210, 211, 212, 214, 215, 217, 222, 228, 238, 239, 241, 242, 249, 251, 253, 257, 258, 259, 260, 270, 274, 282, 283 and 284 at 500 ppm gave more than or equal to 70% control in these tests when compared to the untreated check which showed extensive disease development. Example B: Pyricularia oryzae test in Rice

[0548] The compounds were dissolved in 2% dimethyl sulfoxide / acetone and then mixed with water containing emulsifier to a calibrated spray volume of 30 mL. The test solutions were poured into spray bottles for further applications.

[0549] To test the preventive activity of compounds, healthy young rice plants, raised in the greenhouse, were sprayed with the compounds preparations at the stated application rates inside the spray cabinets using hollow cone nozzles. One day after treatment, the plants were inoculated with a spore suspension containing 1.4 x 106Pyricularia oryzae inoculum. The inoculated plants were then kept in a greenhouse chamber at 24 °C temperature and 95 % relative humidity for disease expression. A visual assessment of the performance of the compounds was carried out by rating the disease severity (0-100% scale) on treated plants 3, 7, 10 and 15 days after application. Efficacy (% control) of the compounds were calculated by comparing the disease rating in the treatment with the one of the untreated, inoculated control plants. The compounds were also assessed for their plant compatibility by recording symptoms like necrosis, chlorosis and stunting.

[0550] Compounds 4, 5, 36, 41, 44, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 65, 73, 74, 77, 80, 89, 95, 97, 98, 116, 121, 122, 126, 158, 161, 174, 175, 176, 179, 184, 186, 188, 190, 191, 195, 200, 208, 209, 214, 215, 216, 223, 234, 235, 241, 242, 243, 250, 259, 260, 265, 270, 274, 279, 282 and 283 at 500 ppm gave more than or equal to 70 % control in these tests when compared to the untreated check which showed extensive disease development.

[0551] Example C: Alternaria solani test in Tomato

[0552] The compounds were dissolved in 2% dimethyl sulfoxide / acetone and then mixed with water containing emulsifier to a calibrated spray volume of 30 m. The test solutions were poured into spray bottles for further applications.

[0553] To test the preventive activity of compounds, healthy young tomato plants, raised in the greenhouse, were sprayed with the compounds at the stated application rates inside the spray cabinets using hollow cone nozzles. One day after treatment, the plants were inoculated with a spore suspension containing 0.24x106Alternaria solani inoculum and 2% malt. The inoculated plants were then kept in a greenhouse chamber at 22-24 °C temperature and 90-95 % relative humidity for disease expression.

[0554] A visual assessment of the performance of the compounds was carried out by rating the disease severity (0-100% scale) on treated plants 3, 7, 10 and 15 days after application. Efficacy (% control) of the compounds was calculated by comparing the disease rating in the treatment with the one of the untreated, inoculated control plants. The compounds were also assessed for their plant compatibility by recording symptoms like necrosis, chlorosis and stunting.

[0555] Compounds 3, 4, 5, 6, 9, 10, 12, 13, 22, 25, 26, 27, 36, 41, 49, 50, 51, 54, 55, 56, 57, 90, 98, 103, 107, 109, 122, 128, 129, 130, 131, 132, 133, 134, 137, 139, 156, 158, 159, 160, 161, 167, 172, 173, 177, 178, 179, 180, 181, 182, 185, 186, 188, 190, 191, 192, 193, 194, 195, 197, 199, 201, 203, 228, 241, 243, 244, 251, 252, 254, 255, 258, 259, 264, 267, 268, 273, 274, 282 and 283 at 500 ppm gave more than or equal to 70 % control in these tests when compared to the untreated check which showed extensive disease development.

[0556] Example D: Botrytis cinerea test in Tomato

[0557] The compounds were dissolved in 2% dimethyl sulfoxide / acetone and then mixed with water containing emulsifier to a calibrated spray volume of 30 mL. The test solutions were poured into spray bottles for further applications.

[0558] To test the preventive activity of the compounds, healthy young tomato plants, raised in the greenhouse, were sprayed with the compound preparation at the stated application rates inside the spray cabinets using hollow cone nozzles. One day after treatment, the plants were inoculated with a spore suspension containing 1.2xl06Botrytis cinerea inoculum and 2% malt. The inoculated plants were then kept in a greenhouse chamber at 18-20 °C temperature and 90-100 % relative humidity for disease expression. A visual assessment of the performance of the compounds was carried out by rating the disease severity (0-100% scale) on treated plants 3, 7 and 10 days after application. Efficacy (% control) of the compounds was calculated by comparing the disease rating in the treatment with the one of the untreated, inoculated control plants. The compounds were also assessed for their plant compatibility by recording symptoms like necrosis, chlorosis & stunting.

[0559] Compounds 10, 21, 23, 30, 32, 37, 39, 43, 44, 49, 50, 51, 52, 53, 54, 55, 56, 57, 59, 129, 130, 133, 160, 166, 169, 172, 174, 179, 180, 181, 183, 188, 195, 224, 255, 271, 273, 281 and 282 at 500 ppm gave more than or equal to 70 % control in these tests when compared to the untreated check which showed extensive disease development.

[0560] Example E: Rhizoctonia solani test in Rice

[0561] The compounds were dissolved in 2% dimethyl sulfoxide / acetone and then mixed with water containing emulsifier to a calibrated spray volume of 30 m. The test solutions were poured into spray bottles for further applications.

[0562] To test the preventive activity of compounds, healthy young rice seedlings / plants, raised in the greenhouse, were sprayed with the active compound preparation at the stated application rates inside the spray cabinets using hollow cone nozzles.

[0563] One day after treatment, the plants were inoculated with an equal quantity of infected rice bran containing Rhizoctonia solani. The inoculated plants were then kept in a greenhouse chamber at 24-25 °C temperature and 90-95 % relative humidity for disease expression.

[0564] A visual assessment of the performance of the compounds was carried out by rating the disease severity (0-100% scale) on treated plants 3, 7, 10 and 15 days after application. Efficacy (% control) of the compounds was calculated by comparing the disease rating in the treatment with the one of the untreated control. The compounds were also assessed for their plant compatibility by recording symptoms like necrosis, chlorosis and stunting.

[0565] Compounds 24, 81, 83, 88 and 184 at 500 ppm gave more than or equal to 70 % control in these tests when compared to the untreated check which showed extensive disease development.

[0566] Example F: Fusarium culmorum test in Wheat

[0567] The compounds were dissolved in 2% dimethyl sulfoxide / acetone and then mixed with water containing emulsifier to a calibrated spray volume of 30 mL. The test solutions were poured into spray bottles for further applications. To test the preventive activity of compounds, healthy young wheat plants, raised in the greenhouse, were sprayed with the active compound preparation at the stated application rates inside the spray cabinets using hollow cone nozzles. One day after treatment, the plants were inoculated with a spore suspension containing 2xl06Fusarium culmorum inoculum with 2% malt. The inoculated plants were then kept in a greenhouse chamber at 24 °C temperature and 80-90 % relative humidity for disease expression.

[0568] A visual assessment of the performance of the compounds was carried out by rating the disease severity (0-100% scale) on treated plants 3, 7, 10 and 15 days after application. Efficacy (% control) of the compounds was calculated by comparing the disease rating in the treatment with the one of the untreated control. The compounds were also assessed for their plant compatibility by recording symptoms like necrosis, chlorosis and stunting.

[0569] Compounds 6, 38, 44, 52, 55, 59, 65, 87, 89, 115, 116, 130, 158, 159, 182, 189, 190, 229, 238, 260, 262 and 276 at 500 ppm gave more than or equal to 70 % control in these tests when compared to the untreated check which showed extensive disease development.

[0570] Example G: Phytophthora infestans test on tomato plants

[0571] The compounds were dissolved in 2% dimethyl sulfoxide / acetone and then mixed with water containing emulsifier to the desired test concentration in a calibrated spray volume of 30 mL. The test solutions were poured into spray bottles for further applications.

[0572] To test the preventive activity of compounds, healthy young tomato plants raised in the greenhouse were sprayed with the active compound preparation at the stated application rates inside the spray cabinets using hollow cone nozzles. One day after treatment, the plants were inoculated with a sporangial suspension (cold sterile water containing 0.24xl06Phytophthora infestans inoculum). After inoculation, the plants were kept in darkness at 15°C during 24 h, and then moved to a greenhouse chamber with 18 °C temperature and 95-100 % relative humidity for disease expression.

[0573] A visual assessment of the performance of the compounds was carried out by rating the disease severity (0-100% scale) on treated plants 3, 7, 10 and 15 days after application. Efficacy (% control) of the compounds was calculated by comparing the disease rating in the treatment with the one of the untreated control. The compounds were also assessed for their plant compatibility by recording symptoms like necrosis, chlorosis and stunting.

[0574] Compounds 1, 3, 4, 9, 10, 11, 12, 13, 14, 17, 18, 19, 20, 21, 23, 24, 29, 30, 33, 36, 37, 41, 45, 47, 49, 50, 51, 53, 54, 55, 56, 62, 65, 70, 73, 74, 75, 76, 77, 78, 81, 83, 85, 86, 87, 88, 89, 90, 94, 95, 96, 97, 98, 101, 103, 106, 107, 108, 109, 110, 115, 116, 121, 122, 128, 129, 130, 131, 132, 133, 134, 137, 138, 139, 140, 142, 148, 150, 154, 155, 156, 157, 158, 159, 160, 161, 162, 172, 173, 180, 181, 186, 190, 191, 192, 193, 194, 200, 228, 241, 243, 245, 249, 250, 251, 252, 257, 258, 259, 260, 269, 270, 271, 275, 280 and 281 at 500 ppm gave more than or equal to 70 % control in these tests when compared to the untreated check which showed extensive disease development. Example H: Corynespora cassiicola test on soybean plants

[0575] The compounds were dissolved in 2 % dimethyl sulfoxide / acetone and then mixed with water containing an emulsifier to the calibrated spray volume of 30 mL. Each spray solution was poured into a spray bottle for further application.

[0576] To test the preventive activity of the compound, healthy young soybean plants, raised in the greenhouse, were sprayed with the active compound preparation at the stated application rate inside the spray cabinets using hollow cone nozzles. One day after treatment, the plants were inoculated with a spore suspension containing 0.5 x 106Corynespora cassiicola inoculum. The inoculated plants were then kept in a greenhouse chamber at 22-24 °C temperature and 90-95 % relative humidity for disease expression. A visual assessment of the performance of the compounds was carried out by rating the disease severity (0-100% scale) on treated plants 3, 7, 10 and 15 days after application. Efficacy (% control) of the compounds was calculated by comparing the disease rating in the treatment with the one of the untreated, inoculated control. The treated plants were also assessed for plant damage by recording symptoms like necrosis, chlorosis and stunting.

[0577] Compounds 2, 3, 49, 54, 55, 132, 276, 277, 278, 279, 280, 281, 282, 283 and 284 at 500 ppm gave more than or equal to 70 % control in these tests when compared to the untreated check which showed extensive disease development.

[0578] Example I: Pseudoperonospora cubensis on cucumber plants

[0579] The compounds were dissolved in 2% dimethyl sulfoxide / acetone and then mixed with water containing emulsifier to the desired test concentration in a calibrated spray volume of 30ml. The test solutions were poured into the spray bottles for further applications.

[0580] To test the preventive activity of compounds, healthy young cucumber plants, raised in the greenhouse were sprayed with the active compound preparation at the stated application rates inside the spray cabinets using hallow cone nozzles. One day after treatment, the plants were inoculated with a conidial spore suspension containing 2 x 104Pseudoperonospora cubensis inoculum. The inoculated plants were then kept in a greenhouse chamber at 23°C temperature & 80-90 % relative humidity for disease expression.

[0581] A visual assessment of the performance of the single compounds was carried out by rating the disease severity (0-100% scale) on treated plants 3, 7, 10 and 15 days after application. Efficacy (% control) of the compounds was calculated by comparing the disease rating in the treatment with the one of the untreated control. The compounds were also assessed for their plant compatibility by recording symptoms like necrosis, chlorosis and stunting.

[0582] Compounds 2, 3, 9, 10, 12, 13, 19, 21, 23, 24, 28, 32, 33, 36, 37, 38, 39, 40, 41, 44, 49, 53, 54, 55, 90, 92, 93, 96, 97, 98, 106, 109, 132, 133, 134, 137, 138, 180, 229, 239, 251, 252, 257, 258, 259, 260, 273 and 281 at 500 ppm gave more than or equal to 70 % control in these tests when compared to the untreated check which showed extensive disease development.

[0583] Example J: Corynespora cassiicola test on tomato plants

[0584] The compounds were dissolved in 2 % dimethyl sulfoxide / acetone and then mixed with water containing an emulsifier to the calibrated spray volume of 30 mL. Each spray solution was poured into a spray bottle for further application.

[0585] To test the preventive activity of the compound, healthy young tomato plants, raised in the greenhouse, were sprayed with the active compound preparation at the stated application rate inside the spray cabinets using hollow cone nozzles. One day after treatment, the plants were inoculated with a spore suspension containing 0.5 x 106Corynespora cassiicola inoculum. The inoculated plants were then kept in a greenhouse chamber at 22-24 °C temperature and 90-95 % relative humidity for disease expression. A visual assessment of the performance of the compounds was carried out by rating the disease severity (0-100% scale) on treated plants 3, 7, 10 and 15 days after application. Efficacy (% control) of the compounds was calculated by comparing the disease rating in the treatment with the one of the untreated but inoculated control. The treated plants were also assessed for plant damage by recording symptoms like necrosis, chlorosis and stunting.

[0586] Compounds 158, 159, 189, 190 and 191 at 500 ppm gave more than or equal to 70 % control in these tests when compared to the untreated check which showed extensive disease development.

[0587] Having described the invention with reference to certain preferred embodiments, other embodiments will become apparent to one skilled in the art from the consideration of the specification. It will be apparent to those skilled in the art that many modifications, both to materials and methods, may be practiced without departing from the scope of the invention.

Claims

CLAIMS:

1. A compound of formula (I),wherein,W is selected from NRWor O; wherein Rwis selected from hydrogen or Ci-Ce-alkyl;R1is selected from the group consisting of hydrogen, halogen, C1-C3 -alkyl, C1-C3-haloalkyl and C3-C6- cycloalkyl;R2is selected from the group consisting of hydrogen, halogen, methyl and methoxy;R3is selected from the group consisting of hydrogen, halogen, Ci-C3-alkyl and Ci-C3-alkoxy;R4is selected from the group consisting of hydrogen, halogen, cyano, Ci-Ce-alkyl, Ci-Ce-alkoxy, Ci- Ce-haloalkyl and Cs-Ce-cycloalkyl;ring E represents a non-aromatic 5- or 6-membered carbocyclic or heterocyclic ring, fused to the phenyl ring D; wherein said non-aromatic 5- or 6-membered heterocyclic ring contains 1, 2 or 3 heteroatoms independently selected from N, NRd, O or S(0)o-2; said ring E is unsubstituted or substituted with one to six substituents independently selected from R5;R5is selected from the group consisting of halogen, cyano, hydroxyl, Ci-Ce-alkyl, C2-C6 -alkenyl, C2- Ce-alkynyl, Ci-Ce-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, Cs-Ce-cycloalkyl, C3-C6- cycloalkyl-Ci-Ce-alkyl, Cs-Ce-cycloalkenyl, Cs-Ce-halocycloalkyl, Ci-Ce-alkoxy, C2-C6-alkenyloxy, C2-Ce-alkynyloxy, Ci-Ce-haloalkoxy, C2-C6-haloalkenyloxy, C2-C6-haloalkynyloxy, C3-C6- cycloalkyloxy, C’,-C(,-cycloalkyloxy-Ci-C(, -alk l. Cs-Ce-halocycloalkyloxy, Ci-Ce-alkylsulfanyl, Ci- Ce-alkylsulfmyl, Ci-Ce-alkylsulfonyl, Ci-Ce-haloalkylsulfanyl, Ci-Ce-haloalkylsulfmyl, Ci-Ce- haloalkylsulfonyl, oxo, thioxo, cyano-Ci-Ce-alkyl, -OC(O)-Ci-C6-alkyl, -OC(O)-Ci-C6-haloalkyl, - C(O)Ra, =N-C1-C6-alkyl, =N-Ci-C6-haloalkyl, -NRaRb, =N-ORCand =N-NH-RCX; ortwo R5groups when attached to the same carbon atom, together with the carbon atom to which they are attached, may form a 3- to 6-membered non-aromatic carbocyclic or non-aromatic heterocyclic ring, wherein said heterocyclic ring contains 1, 2 or 3 heteroatoms independently selected from N, NRd, O or S(0)o-2;Rais selected from the group consisting of hydrogen, halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci- Ce -alkoxy, Ci-Ce-haloalkoxy and C3-C6 -cycloalkyl;Rbis selected from the group consisting of hydrogen, halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci- Ce-alkoxy, Ci-Ce-haloalkoxy and Cs-Ce-cycloalkyl;Rcis selected from the group consisting of hydrogen, halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci- Ce -alkoxy, Ci-Ce-haloalkoxy, C3-C6 -cycloalkyl, C^-Ce-cycloalkyl-C’i-Ce-alkyl. phenyl, phenyl-Ci- Ce -alkyl- and -C(O)RX; wherein said phenyl ring is unsubstituted or substituted with one to three substituents independently selected from halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-Ce -alkoxy, Ci- Ce-haloalkoxy and Cs-Ce-cycloalkyl;Rcxis selected from the group consisting of hydrogen, halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci- Ce-alkoxy, Ci-Ce-haloalkoxy, Cs-Ce-cycloalkyl, -C(O)-Ci-C6-alkyl and -C(O)-Ci-C6-haloalkyl; Rdis selected from the group consisting of hydrogen, halogen, C1-C8-alkyl, Ci-Ce-haloalkyl, Ci- Ce-alkoxy, Ci-Ce-haloalkoxy, Cs-Ce-cycloalkyl, C^-Ce-cycloalkyl-C’i-Ce-alkyl and -C(O)Ra; Rxis selected from the group consisting of hydrogen, halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci- Ce-alkoxy, Ci-Ce-haloalkoxy, Cs-Ce-cycloalkyl, C^-Ce-cycloalkyl-C’i-Ce-alkyl and phenyl; wherein said phenyl ring is unsubstituted or substituted with one to three substituents independently selected from halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-Ce-alkoxy, Ci-Ce- haloalkoxy and Cs-Ce-cycloalkyl; andR6is selected from hydrogen or Ci-C3-alkyl;or salts, stereoisomers, tautomers, polymorphs or N-oxides thereof.

2. The compound of formula (I) or salts, stereoisomers, tautomers, polymorphs, or N-oxides thereof according to claim 1, wherein R1is selected from the group consisting of hydrogen, halogen and Ci- C3-alkyl.

3. The compound of formula (I) or salts, stereoisomers, tautomers, polymorphs, or N-oxides thereof according to claim 1 or claim 2, wherein R2and R3are hydrogen.

4. The compound of formula (I) or salts, stereoisomers, tautomers, polymorphs, or N-oxides thereof according to any one of claims 1 to 3, wherein R4is selected from the group consisting of hydrogen, halogen, cyano and Ci-C3-alkyl.

5. The compound of formula (I) or salts, stereoisomers, tautomers, polymorphs, or N-oxides thereof according to any one of claims 1 to 4, wherein R5is selected from the group consisting of halogen, cyano, hydroxyl, Ci-C-ralkyl, Ci-C -haloalkyl. C\-C(, -cycloalkyl. CNCe-halocycloalkyl. C1-C4- alkoxy, Ci-Ohaloalkoxy. CNCe-cycloalkyloxy. Ci-C4-alkylsulfanyl, Ci-C4-alkylsulfmyl, C1-C4- alkylsulfonyl, Ci-C4-haloalkylsulfanyl, Ci-C4-haloalkylsulfmyl, Ci-C4-haloalkylsulfonyl, oxo, thioxo, cyano-Ci-C4-alkyl, -OC(O)-Ci-C6-alkyl, -OC(O)-Ci-C6-haloalkyl, -C(O)Ra, =N-Ci-C6-alkyl, =N-Ci-C6-haloalkyl, -NRaRb, =N-ORCand =N-NH-RCX.

6. The compound of formula (I) or salts, stereoisomers, tautomers, polymorphs, or N-oxides thereof according to any one of claims 1 to 5, wherein W is an oxygen atom (O).

7. The compound of formula (I) or salts, stereoisomers, tautomers, polymorphs, or N-oxides thereofaccording to any one of claims 1 to 6, wherein the fragmentis selected from DE-1 to DE-20;wherein indicates the point of attachment to the phenyl ring containing the acrylyl group and R4, Rdand R5are as defined in claim 1.

8. The compound of formula (I) or salts, stereoisomers, tautomers, polymorphs, or N-oxides thereof according to any one of claims 1 to 7, wherein R6is C1-C3 -alkyl.

9. The compound of formula (I) or salts, stereoisomers, tautomers, polymorphs, or N-oxides thereof according to claim 1, whereinW is selected from NRWor O; wherein Rwis hydrogen;R1is selected from the group consisting of hydrogen, halogen and Ci-C3-alkyl;R2and R3are hydrogen;R4is selected from the group consisting of hydrogen, halogen, cyano and C1-C3 -alkyl;ring E represents a non-aromatic 5- or 6-membered carbocyclic or heterocyclic ring, fused to the phenyl ring D; wherein said non-aromatic 5- or 6-membered heterocyclic ring contains 1 or 2heteroatoms independently selected from N, NRd, O or S; said ring E is unsubstituted or substituted with one to four substituents independently selected from R5;R5is selected from the group consisting of halogen, cyano, hydroxyl, Ci-C-ralkyl, Ci-C4-haloalkyl, C\-G, -cycloalkyl. Cs-Ce-halocycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Cs-Ce-cycloalkyloxy, Ci- C4-alkylsulfanyl, Ci-C4-alkylsulfinyl, Ci-C4-alkylsulfonyl, Ci-C4-haloalkylsulfanyl, C1-C4- haloalkylsulfmyl, Ci-C4-haloalkylsulfonyl, oxo, thioxo, cyano-Ci-C4-alkyl, -OC(O)-Ci-C6-alkyl, - OC(O)-Ci-C6-haloalkyl, -C(O)Ra, =N-Ci-C6-alkyl, =N-Ci-C6-haloalkyl, -NRaRb, =N-ORCand =N- NH-RCX; ortwo R5groups when attached to the same carbon atom, together with the carbon atom to which they are attached, may form a 3 - to 5 -membered non-aromatic carbocyclic ring;Rais selected from the group consisting of hydrogen, halogen and Ci-C4-alkyl;Rbis selected from the group consisting of hydrogen, halogen, C1-C3 -alkyl, and C1-C3 -alkoxy; Rcis selected from the group consisting of hydrogen, Ci-C4-alkyl, Cs-Ce-cycloalkyl, C3-C5- cycloalkyl-Ci-C3-alkyl, phenyl, phenyl-Ci-C3-alkyl and -C(O)RXwherein said phenyl ring is unsubstituted or substituted with one substituent selected from halogen, Ci-C3-alkyl, C1-C3- haloalkyl, Ci-C3-alkoxy and Ci-C3-haloalkoxy;Rcxis selected from the group consisting of hydrogen, Ci-C3-alkyl, Ci-C3-alkoxy, -C(O)-Ci-C3- alkyl and -C(O)-Ci-C3-haloalkyl;Rdis selected from the group consisting of hydrogen, halogen, Ci-Ce-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C3-C6 -cycloalkyl, C^-Ce-cycloalkyl-C’i-C’, -alkyl and -C(O)Ra; Rxis selected from the group consisting of Ci-Ce-alkyl, C3-C6 -cycloalkyl and C3-C6 -cycloalkyl - Ci-C2-alkyl; andR6is Ci-C3-alkyl.

10. An agrochemical composition comprising the compound of formula (I) according to claim 1 and an additional agrochemically acceptable auxiliary.

11. The composition according to claim 10, wherein said composition further comprises an additional active ingredient selected from the group consisting of fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, safeners, plant growth regulators, antibiotics, fertilizers and nutrients.

12. A method of controlling or preventing infestation of plants by phytopathogenic fungi in agricultural crops or horticultural crops, wherein an effective amount of the compound of formula (I) according to claim 1, or the composition according to claim 10, is applied to the plants, plant parts or locus thereof, soil, seeds or materials to be protected against fungal attack.

13. Use of the compound of formula (I) according to claim 1, as a fungicide.

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