Fungicidal compounds

Abstract

The present invention relates to fungicidal compounds. Disclosed are compounds of formula (I) wherein the substituents are as defined in claim 1, which can be used as pesticides, in particular fungicides. # imgabs0 #

Description

[0001] This application is a divisional application of the parent case, Chinese invention patent application No. 202080022613.9. Technical Field

[0002] The present invention relates to microbicidal methoxyacrylate derivatives, for example as active ingredients, which have microbicidal activity, in particular fungicidal activity. The present invention also relates to agrochemical compositions comprising at least one of these methoxyacrylate derivatives, processes for the preparation of these compounds, and the use of these methoxyacrylate derivatives or compositions in agriculture or horticulture for controlling or preventing infection of plants, harvested food crops, seeds or non-living materials by phytopathogenic microorganisms, preferably fungi. Background Art

[0003] EP 0 212 859 and WO 98 / 03464 describe the use of strobilurin derivatives for combating phytopathogenic fungi. SUMMARY OF THE INVENTION

[0004] According to the present invention, there is provided a compound having formula (I)

[0005]

[0006] in

[0007] R 1 selected from the group consisting of: hydrogen, halogen, methyl and methoxy;

[0008] R 2 selected from the group consisting of: hydrogen, halogen, methyl and methoxy;

[0009] R 3 selected from the group consisting of: hydrogen, halogen, methyl and methoxy;

[0010] R 4 is C3-C7 cycloalkyl or C3-C7 cycloalkenyl, wherein the cycloalkyl or cycloalkenyl is optionally substituted by 1, 2 or 3 R which may be the same or different 5 Substituent substitution;

[0011] R 5Selected from the group consisting of halogen, hydroxy, cyano, C1-C4 alkyl, C2-C4 alkenyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, cyano C1-C4 alkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C3-C6 cycloalkyl C1-C4 alkyl-, C3-C6 cycloalkyl C2-C6 alkenyl-, C1-C4 alkoxy, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C1-C4 haloalkoxy, C3-C6 cycloalkyl C1-C4 alkoxy-, C1-C3 alkoxy C1-C3 alkoxy-, C1-C5 alkoxy C1-C3 alkyl-, (=NOR 6 ), (=O), phenoxy C1-C3 alkyl-, heteroaryloxy C1-C3 alkyl-, phenoxy and heteroaryloxy, wherein the heteroaryl moiety is a 5- or 6-membered aromatic ring containing 1, 2, 3 or 4 heteroatoms independently selected from nitrogen, oxygen and sulfur, and wherein the phenyl or heteroaryl moiety is optionally substituted by 1, 2 or 3 R which may be the same or different 7 Substituent substitution;

[0012] R 6 Selected from the group consisting of C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C2 alkyl-, C3-C6 alkynyl, C3-C6 alkenyl and C3-C6 haloalkenyl;

[0013] R 7 is selected from the group consisting of fluorine, chlorine, cyano, hydroxy, methyl, ethyl, methoxy, ethoxy, difluoromethyl, trifluoromethyl, difluoromethoxy and trifluoromethoxy,

[0014] or an agronomically acceptable salt thereof;

[0015] or an N-oxide thereof.

[0016] It has been found that the novel compounds of formula (I) have a very advantageous level of biological activity for protecting plants against diseases caused by fungi.

[0017] According to a second aspect of the present invention, there is provided an agrochemical composition comprising a fungicidally effective amount of a compound of formula (I) and an agrochemically acceptable diluent or carrier. Such an agricultural composition may further comprise at least one additional active ingredient.

[0018] According to a third aspect of the present invention, there is provided a method for controlling or preventing infection of useful plants by phytopathogenic microorganisms, wherein a fungicidally effective amount of a compound of formula (I), or a composition comprising such a compound as an active ingredient, is applied to the plant, its part or its locus.

[0019] According to a fourth aspect of the present invention there is provided the use of a compound of formula (I) as a fungicide. According to this particular aspect of the present invention the use may not comprise a method of treating the human or animal body by surgery or therapy. DETAILED DESCRIPTION OF THE INVENTION

[0021] As used herein, the term "halogen" or "halo" refers to fluorine (fluoro), chlorine (chloro), bromine (bromo) or iodine (iodo), preferably fluorine, chlorine or bromine.

[0022] As used herein, cyano refers to a -CN group.

[0023] As used herein, hydroxyl means an -OH group.

[0024] As used herein, the term "C1-C6 alkyl" refers to a straight or branched hydrocarbon chain radical consisting solely of carbon and hydrogen atoms, containing no unsaturation, having from one to six carbon atoms, and attached to the remainder of the molecule by a single bond. C1-C4 alkyl and C1-C2 alkyl should be interpreted accordingly. Examples of C1-C6 alkyl include, but are not limited to, methyl, ethyl, n-propyl, 1-methylethyl (isopropyl), n-butyl, and 1-dimethylethyl (tert-butyl).

[0025] As used herein, the term "cyano C1-C6 alkyl" refers to a C1-C6 alkyl group as generally defined above, which is substituted with one or more cyano groups. "Cyano C1-C4 alkyl-" should be interpreted accordingly.

[0026] As used herein, the term "C1-C6 alkoxy" refers to a group having the formula -OR a A group in which R a is C as defined above 1- C6 alkyl group. "C1-C4 alkoxy" should be interpreted accordingly. Examples of C1-C6 alkoxy include, but are not limited to, methoxy, ethoxy, propoxy, isopropoxy and tert-butoxy.

[0027] As used herein, the term "C1-C6 haloalkyl" refers to a C1-C6 alkyl group as generally defined above, which is substituted by one or more identical or different halogen atoms. C1-C4 haloalkyl should be interpreted accordingly. Examples of C1-C6 haloalkyl include, but are not limited to, chloromethyl, fluoromethyl, fluoroethyl, difluoromethyl, trifluoromethyl and 2,2,2-trifluoroethyl.

[0028] As used herein, the term "C1-C6 haloalkoxy" refers to a C1-C6 alkoxy group as defined above, which is substituted by one or more identical or different halogen atoms. C1-C4 haloalkoxy should be interpreted accordingly. Examples of C1-C6 haloalkoxy include, but are not limited to, fluoromethoxy, difluoromethoxy, fluoroethoxy, trifluoromethoxy and trifluoroethoxy.

[0029] As used herein, the term "C3-C6 cycloalkylC1-C4 alkoxy-" refers to a C1-C4 alkoxy group as generally defined above, substituted with one or more C3-C6 cycloalkyl groups as generally defined below.

[0030] As used herein, the term "C2-C6 alkenyl" refers to a straight or branched hydrocarbon chain radical consisting solely of carbon atoms and hydrogen atoms, containing at least one double bond which may have an (E)- or (Z)-configuration, having from two to six carbon atoms, attached to the remainder of the molecule by a single bond. C2-C4 alkenyl should be interpreted accordingly. Examples of C2-C6 alkenyl include, but are not limited to, prop-1-enyl, allyl (prop-2-enyl) and but-1-enyl.

[0031] As used herein, the term "C2-C6 haloalkenyl" refers to a C2-C6 alkenyl group as generally defined above, substituted by one or more halogen atoms which may be the same or different.

[0032] As used herein, the term "C2-C6 alkynyl" refers to a straight or branched hydrocarbon chain radical consisting solely of carbon and hydrogen atoms, containing at least one triple bond, having from two to six carbon atoms, and attached to the remainder of the molecule by a single bond. Examples of C2-C6 alkynyl groups include, but are not limited to, prop-1-ynyl and propargyl (prop-2-ynyl).

[0033] As used herein, the term "C1-C3 alkoxy C1-C3 alkyl-" refers to a a -OR b - a group, wherein R a is a C2-C3 alkyl group as generally defined above, and R b is a C1-C2 alkylene group as generally defined above.

[0034] As used herein, the term "C1-C3 alkoxy C1-C3 alkoxy-" refers to a a -OR b -O- group, where R a is a C1-C3 alkyl group as generally defined above, and R b is a C1-C3 alkyl group as generally defined above.

[0035] As used herein, the term "C3-C7 cycloalkyl" refers to a stable monocyclic group that is fully saturated and contains 3 to 7 carbon atoms. C3-C4 cycloalkyl should be interpreted accordingly. Examples of C3-C7 cycloalkyl include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

[0036] As used herein, the term "C3-C7 cycloalkenyl" refers to a stable monocyclic group that is partially unsaturated and contains 3 to 7 carbon atoms. C3-C4 cycloalkenyl should be interpreted accordingly. Examples of C3-C7 cycloalkenyl include, but are not limited to, cyclopentene-1-yl, cyclohexene-1-yl and cycloheptene-1-yl.

[0037] As used herein, the term "C3-C6 cycloalkylC1-C4 alkyl-" refers to a C1-C4 alkyl group as generally defined above, substituted with one or more C3-C6 cycloalkyl groups as generally defined above.

[0038] As used herein, the term "C3-C6 cycloalkylC2-C6 alkenyl-" refers to a C2-C6 alkenyl group as generally defined above, substituted by one or more C3-C6 cycloalkyl groups as generally defined above.

[0039] As used herein, the term "C3-C6 cycloalkylC2-C3 alkynyl-" refers to a C2-C3 alkynyl group as generally defined above, which is substituted by one or more C3-C6 cycloalkyl groups as generally defined above.

[0040] As used herein, the term "C3-C6 halocycloalkyl" refers to a C3-C6 cycloalkyl group as generally defined above, which is substituted by one or more halogen atoms, which may be the same or different. C3-C4 halocycloalkyl should be interpreted accordingly.

[0041] As used herein, the term "C1-C6 alkoxy C3-C6 cycloalkyl-" refers to a C3-C6 cycloalkyl group as defined above, substituted by one or more C1-C6 alkoxy groups as generally defined above.

[0042] As used herein, the term "C1-C2alkylC3-C6cycloalkyl-" refers to a C3-C6cycloalkyl group as defined above, which is substituted by one or more C1-C2alkyl groups as defined above.

[0043] As used herein, the term "phenoxy C1-C3 alkyl-" refers to a phenoxy group attached via an oxygen atom to a C1-C3 alkyl group as generally defined above. 1- A phenyl ring of a C3 alkylene group.

[0044] As used herein, unless otherwise expressly stated, the term "heteroaryl" refers to a 5- or 6-membered monocyclic aromatic ring containing 1, 2, 3 or 4 heteroatoms selected individually from nitrogen, oxygen and sulfur. The heteroaryl group may be bonded to the remainder of the molecule via a carbon atom or a heteroatom. Examples of heteroaryl groups include furanyl, pyrrolyl, imidazolyl, thienyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, triazolyl, tetrazolyl, pyrazinyl, pyridazinyl, pyrimidinyl or pyridyl.

[0045] As used herein, the term "heteroaryloxy C1-C3 alkyl-" refers to a C1-C3 alkyl radical attached to the C1-C3 alkyl radical as generally defined above via an oxygen atom. 1- The heteroaryl ring of the C3 alkylene group is as defined above.

[0046] The presence of one or more possible asymmetric carbon atoms in compounds of formula (I) means that these compounds can exist in chiral isomeric forms (i.e., enantiomers or diastereoisomers). As a result of restricted rotation around a single bond, atropisomers may also exist. Formula (I) is intended to include all those possible isomeric forms and mixtures thereof. The present invention includes all those possible isomeric forms of compounds of formula (I) and mixtures thereof. Similarly, formula (I) is intended to include all possible tautomers (including lactam-lactim tautomerism and keto-enol tautomerism) (when present). The present invention includes all possible tautomeric forms of compounds of formula (I).

[0047] In each case, the compounds of formula (I) according to the invention are in free form, in covalently hydrated form or in salt form (eg an agronomically usable or agrochemically acceptable salt form).

[0048] The following list provides information on the substituents R of the compounds of formula (I) according to the present invention. 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 For any of these substituents, any definition given below may be combined with any definition of any other substituent given below or elsewhere in this document.

[0049] R 1 is selected from the group consisting of hydrogen, halogen, methyl and methoxy. 1 is selected from the group consisting of hydrogen, chlorine, fluorine, bromine, methyl and methoxy. More preferably, R 1 is selected from the group consisting of chlorine, fluorine, bromine, methyl and methoxy. Even more preferably, R1 is selected from the group consisting of chlorine, bromine and methyl. Most preferably, R 1 It's methyl.

[0050] R 2 is selected from the group consisting of hydrogen, halogen, methyl and methoxy. 2 is selected from the group consisting of hydrogen, fluorine, methyl and methoxy. More preferably, R 2 is selected from the group consisting of hydrogen, fluorine and methyl. Even more preferably, R 2 is hydrogen or fluorine. Most preferably, R 2 It's hydrogen.

[0051] R 3 is selected from the group consisting of hydrogen, halogen, methyl and methoxy. 3 is selected from the group consisting of hydrogen, fluorine, methyl and methoxy. More preferably, R 3 is selected from the group consisting of hydrogen, fluorine and methyl. Even more preferably, R 3 is hydrogen or fluorine. Most preferably, R 3 It's hydrogen.

[0052] R 4 is C3-C7 cycloalkyl or C3-C7 cycloalkenyl, wherein the cycloalkyl or cycloalkenyl is optionally substituted by 1, 2 or 3 R which may be the same or different 5 Preferably, R 4 is a C3-C7 cycloalkyl group, wherein the cycloalkyl group is optionally substituted by 1, 2 or 3 R groups which may be the same or different 5 More preferably, R 4 is optionally replaced by 1 or 2 R which may be the same or different 5 More preferably, R 4 is optionally replaced by 1 R 5 More preferably, R 4 Selected from the group consisting of: optionally 1 R 5 substituted cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. Still even more preferably, R 4 is selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. Still further preferably, R 4 is cyclopentyl or cyclohexyl. Most preferably, R 4 It is cyclohexyl.

[0053] In one embodiment, R 4 is optionally replaced by 1 R 5 The substituent is a cyclohexyl group substituted with the substituent.

[0054] Each R 5 independently selected from the group consisting of halogen, hydroxy, cyano, C1-C4 alkyl, C2-C4 alkenyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, cyano C1-C4 alkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C3-C6 cycloalkyl C1-C4 alkyl-, C3-C6 cycloalkyl C2-C6 alkenyl-, C1-C4 alkoxy, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C1-C4 haloalkoxy, C3-C6 cycloalkyl C1-C4 alkoxy-, C1-C3 alkoxy C1-C3 alkoxy-, C1-C5 alkoxy C1-C3 alkyl-, (=NOR 6 ), (=O), phenoxy C1-C3 alkyl-, heteroaryloxy C1-C3 alkyl-, phenoxy and heteroaryloxy, wherein the heteroaryl moiety is a 5-membered or 6-membered aromatic ring containing 1, 2, 3 or 4 heteroatoms independently selected from nitrogen, oxygen and sulfur, and wherein the phenyl or heteroaryl moiety is optionally substituted by 1, 2 or 3 R which may be the same or different 7 Substituent substitution.

[0055] Preferably, each R 5 independently selected from the group consisting of halogen, hydroxy, cyano, C1-C4 alkyl, C2-C4 alkenyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, cyano C1-C4 alkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C3-C6 cycloalkyl C1-C4 alkyl-, C3-C6 cycloalkyl C2-C6 alkenyl-, C1-C4 alkoxy, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C1-C4 haloalkoxy, C3-C6 cycloalkyl C1-C4 alkoxy-, C1-C3 alkoxy C1-C3 alkoxy-, C1-C5 alkoxy C1-C3 alkyl-, (=NOR 6 ), (=O), phenoxy C1-C3 alkyl-, heteroaryloxy C1-C3 alkyl-, phenoxy and heteroaryloxy, wherein the heteroaryl moiety is a 5-membered or 6-membered aromatic ring containing 1, 2, 3 or 4 heteroatoms independently selected from nitrogen, oxygen and sulfur, and wherein the phenyl or heteroaryl moiety is optionally replaced by 1 R 7 Substituent substitution.

[0056] More preferably, each R 5independently selected from the group consisting of halogen, hydroxy, cyano, C1-C4 alkyl, C2-C4 alkenyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, cyano C1-C4 alkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C3-C6 cycloalkyl C1-C4 alkyl-, C3-C6 cycloalkyl C2-C6 alkenyl-, C1-C4 alkoxy, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C1-C4 haloalkoxy, C3-C6 cycloalkyl C1-C4 alkoxy-, C1-C3 alkoxy C1-C3 alkoxy-, C1-C5 alkoxy C1-C3 alkyl-, (=NOR 6 ) and (=O).

[0057] Even more preferably, each R 5 independently selected from the group consisting of halogen, hydroxyl, cyano, C1-C4 alkyl, C2-C4 alkenyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C3-C6 cycloalkylC1-C4 alkyl-, C3-C6 cycloalkylC2-C6 alkenyl-, C1-C4 alkoxy, C1-C4 haloalkoxy, (=NOR 6 ) and (=O).

[0058] Even more preferably, each R 5 Selected from the group consisting of halogen, C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, (=NOR 6 ) and (=O).

[0059] Still even more preferably, each R 5 Selected from the group consisting of fluoro, methyl, trifluoromethyl, cyclopropyl, (=NOCH3) and (=O).

[0060] In one embodiment, R 5 Selected from the group consisting of fluoro, hydroxy, cyano, methyl, isopropyl, difluoromethyl, trifluoromethyl, cyclopropyl, difluoromethoxy, (=NOCH3), (=NOCH2CH3) and (=O).

[0061] R 6 is selected from the group consisting of C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C2 alkyl-, C3-C6 alkynyl, C3-C6 alkenyl and C3-C6 haloalkenyl. 6 is selected from the group consisting of C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 alkynyl and C3-C6 alkenyl. More preferably, R 6 is C1-C6 alkyl. Even more preferably, R 6 is a C1-C3 alkyl group, most preferably R6 It's methyl.

[0062] Each R 7 is independently selected from the group consisting of fluorine, chlorine, cyano, hydroxy, methyl, ethyl, methoxy, ethoxy, difluoromethyl, trifluoromethyl, difluoromethoxy and trifluoromethoxy. 7 is independently selected from the group consisting of fluorine, chlorine, methyl, ethyl, methoxy, ethoxy, difluoromethyl and trifluoromethyl. Even more preferably, each R 7 Independently selected from the group consisting of fluoro, chloro, methyl and ethyl.

[0063] Preferably, in the compounds according to formula (I) of the present invention:

[0064] R 1 selected from the group consisting of chloro, fluoro, bromo, methyl and methoxy;

[0065] R 2 is hydrogen or fluorine;

[0066] R 3 is hydrogen or fluorine;

[0067] R 4 is C3-C7 cycloalkyl or C3-C7 cycloalkenyl, wherein the cycloalkyl or cycloalkenyl is optionally substituted by 1, 2 or 3 R which may be the same or different 5 Substituent substitution;

[0068] Each R 5 Selected from the group consisting of halogen, C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, (=NOR 6 ) and (=O); and

[0069] R 6 It is a C1-C3 alkyl group.

[0070] More preferably, in the compounds according to formula (I) of the present invention:

[0071] R 1 It is methyl;

[0072] R 2 It is hydrogen;

[0073] R 3 is hydrogen or fluorine;

[0074] R 4 is optionally replaced by 1, 2 or 3 R 5 a C3-C7 cycloalkyl substituted with a substituent; and

[0075] Each R 5Selected from the group consisting of fluoro, methyl, trifluoromethyl, cyclopropyl, (=NOCH3) and (=O).

[0076] Even more preferably, in the compounds according to formula (I) of the present invention:

[0077] R 1 It is methyl;

[0078] R 2 It is hydrogen;

[0079] R 3 It is hydrogen;

[0080] R 4 is selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl, wherein the cyclopropyl is optionally substituted with 1 R 5 Substituents are substituted; and

[0081] R 5 It is cyclopropyl.

[0082] Even more preferably, in the compounds according to formula (I) of the present invention,

[0083] R 1 It is methyl;

[0084] R 2 It is hydrogen;

[0085] R 3 It is hydrogen;

[0086] R 4 It is cyclopentyl or cyclohexyl.

[0087] In one group of embodiments, the compound according to formula (I) is selected from compounds E.1 to E.23 or F.1 to F.10 listed in Tables E and F below.

[0088] According to the present invention, there is also provided an intermediate having the formula (XIb),

[0089]

[0090] in,

[0091] R 1 It is methyl;

[0092] R 2 It is hydrogen;

[0093] R 3 It is hydrogen;

[0094] R 4 is selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl (preferably, R 4is cyclopentyl or cyclohexyl); and

[0095] R 13 is H or C1-C4 alkyl (preferably, R 13 is methyl).

[0096] In another embodiment of the present invention, there is also provided an intermediate having the formula (XIc),

[0097]

[0098] in,

[0099] R 1 It is methyl;

[0100] R 2 It is hydrogen;

[0101] R 3 It is hydrogen;

[0102] R 4 is selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl (preferably, R 4 is cyclopentyl or cyclohexyl); and

[0103] R 14 is H or C1-C4 alkyl (preferably, R 14 is methyl).

[0104] In one embodiment, the compounds of formula (I) according to the invention can be used against phytopathogenic fungi (e.g. Alternaria alternata, Phakopsora pachyrhizi, Plasmopara viticola, Sclerotinia sclerotiorum or Septoria tritici (also known as Mycosphaerella graminicola)) containing a mutation in mitochondrial cytochrome b that confers resistance to Qo inhibitors (e.g. strobilurins such as azoxystrobin, pyraclostrobin, picoxystrobin and trifloxystrobin or fenamidone or famoxadone).

[0105] In another embodiment, the compounds of formula (I) according to the invention can be used against phytopathogenic fungi containing a mutation in mitochondrial cytochrome b (e.g. Alternaria alternata, Plasmopara viticola, Sclerotinia sclerotiorum or Septoria graminicola (also known as Mycosphaeria graminicola)) which confers resistance to Qo inhibitors (e.g. strobilurins such as azoxystrobin, pyraclostrobin, picoxystrobin and trifloxystrobin or fenamidone or famoxadone), wherein the mutation is G143A.

[0106] In another embodiment, the compounds of formula (I) according to the invention can be used against phytopathogenic fungi (e.g. Psoralea pachyrhizi) containing a mutation in mitochondrial cytochrome b that confers resistance to Qo inhibitors (e.g., strobilurins such as azoxystrobin, pyraclostrobin, picoxystrobin and trifloxystrobin or fenamidone or famoxadone), wherein the mutation is F129L.

[0107] In another embodiment, the present invention also relates to a method of controlling or preventing infestation of phytopathogenic fungi in plants (e.g., Nicotiana tabacum, Plasmopara viticola, Sclerotinia sclerotiorum or Septoria graminearum (also known as Mycosphaeria graminearum)), wherein the phytopathogenic fungi contain a mutation in mitochondrial cytochrome b, thereby conferring resistance to Qo inhibitors (e.g., strobilurins, such as azoxystrobin, pyraclostrobin, picoxystrobin and trifloxystrobin or fenamidone or oxadiazon), the method comprising applying to the plant, part thereof or the locus thereof a fungicidally effective amount of a compound having formula (I). Preferably, a method of controlling or preventing infection of phytopathogenic fungi (e.g., Psora pachyrhizium) in soybean plants, wherein the phytopathogenic fungi contains a mutation in mitochondrial cytochrome b, thereby conferring resistance to Qo inhibitors (e.g., strobilurins, such as azoxystrobin, pyraclostrobin, picoxystrobin and trifloxystrobin or fenamidone or famoxadone), the method comprising applying to the plant, part thereof, or the locus thereof a fungicidally effective amount of a compound of formula (I). More preferably, a method of controlling or preventing infection of phytopathogenic fungi (e.g., Psora pachyrhizium) in soybean plants, wherein the phytopathogenic fungi contains a F129L mutation in mitochondrial cytochrome b, thereby conferring resistance to Qo inhibitors (e.g., strobilurins, such as azoxystrobin, pyraclostrobin, picoxystrobin and trifloxystrobin or fenamidone or famoxadone), the method comprising applying to the plant, part thereof, or the locus thereof a fungicidally effective amount of a compound of formula (I).

[0108] The level of resistance, and therefore the impact on the performance of the fungicide, can be measured by using the 'resistance factor (RF). The resistance factor can be calculated by dividing the concentration of the fungicide that provides a preset level of disease control (i.e. 50%) for a 'resistant' fungal strain by the concentration of the fungicide that provides the same level of disease control for a 'susceptible' strain of the same fungal species (RF = EC50 value for resistant strain / EC50 value for sensitive strain). Although there are no set rules, three categories can be defined: 1) RF ≥ 50 = resistant strains, 2) 5 ≤ RF < 50 = less sensitive strains (variable sensitivity), and 3) RF < 5 = sensitive strains.

[0109] To obtain resistant fungal strains, researchers locate host crops and geographic areas where relevant resistance has been reported in the literature or has been observed in agronomic practice. Leaf samples infected with the target disease or spores, or mycelium of the target disease, are then collected from these locations / host crops and sent to the laboratory where pure cultures are isolated. The resistance phenotype of the fungal culture is determined by performing a full dose response bioassay and comparing the bioassay results with similar bioassay results for known susceptible strains of the same species. Alternatively, if the resistance mechanism for the relevant species is known, the resistance genotype of the fungal strain can be determined by molecular techniques (e.g., qPCR).

[0110] Unless otherwise stated, the compounds of formula (I) according to the present invention can be prepared as shown in the following Schemes 1 to 16, wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 is as defined for the compound of formula (I).

[0111] A compound having formula (II) (wherein R 1 , R 2 , R 3 and R 4 As defined above, and R 16 As defined in Scheme 1), a compound of formula (III) wherein R 1 , R 2 and R3 As defined for compounds of formula (I), R 16 As defined in Scheme 1 and R 11 is a halide or pseudohalide such as chlorine, bromine, iodine, -OSO2CF3 or -OSO2(CF2)3CF3) and a compound having formula (IV) (wherein R 4 As defined for compounds of formula (I), and M is a metalloid species or a pseudo-metalloid species (e.g., M includes but is not limited to MgCl, ZnCl or B(OH)2)). For related examples, see: Journal of Organic Chemistry, 2010, 75, 6677-6680, Journal of the American Chemical Society, 2009, 131, 7532-7533, European Journal of Medicinal Chemistry, 2018, 147, 238-252, and "Cross-Coupling Reactions: A Practical Guide (Topics in Current Chemistry)" edited by Norio Miyaura and SL Buchwald (Springer edition), or by Armin de Meijere and Diederich, ed., "Metal-Catalyzed Cross-Coupling Reactions" (WILEY-VCH ed.). This is shown in Scheme 1.

[0112]

[0113] Solution 1

[0114] Alternatively, the compound of formula (II) may be prepared by reacting a compound of formula (V) (wherein R 1 , R 2 and R 3 As defined for compounds of formula (I), R 16 As defined in Scheme 2, and R 12(a partially unsaturated, optionally substituted C3-C7 cycloalkenyl) is obtained by reaction via a reduction method (e.g., hydrogenation using a hydrogen source in the presence of a catalyst complex such as palladium on carbon in an organic solvent such as methanol, tetrahydrofuran or ethyl acetate at a temperature between 0°C and 150°C). For relevant examples, see: ACS Medicinal Chemistry Letters, 2016, 7, 508-51; Shigeo Nishimura's 'Handbook of Heterogeneous Catalytic Hydrogenation for Organic Synthesis' (published by Wiley-VCH) or Johannes de Vries and Cornelis Elsevier's 'The Handbook of Homogeneous Hydrogenation' (published by Wiley-VCH). This is shown in Scheme 2.

[0115]

[0116] Solution 2

[0117] A compound having formula (V) (wherein R 1 , R 2 and R 3 As defined for compounds of formula (I), R 16 As defined in Scheme 3, and R 12 is a partially saturated and optionally substituted C3-C7 cycloalkenyl) can be reacted via a compound (R) of formula (III) using a suitable catalyst complex such as palladium (tetrakistriphenylphosphine) in a solvent such as 1,4-dioxane, dimethylformamide or tetrahydrofuran at a temperature between 0°C and 150°C and optionally in the presence of a base such as potassium phosphate. 11It is obtained by a cross-coupling reaction between a halide or pseudohalide such as chlorine, bromine, iodine, -OSO2CF3 or -OSO2(CF2)3CF3) and a compound of formula (VI) (wherein M represents a metalloid or pseudometalloid species (e.g., M includes but is not limited to B(OH)2, BPin, SnBu3) or hydrogen). For relevant examples, see: ACS Medicinal Chemistry Letters, 2016, 7, 508-513 and "Cross-Coupling Reactions: A Practical Guide (Topics in Current Chemistry)" edited by Norio Miyaura and SL Buchwald (Springer Edition), or by Armin de Meijere and Diederich, ed., "Metal-Catalyzed Cross-Coupling Reactions" (WILEY-VCH ed.). This is shown in Scheme 3.

[0118]

[0119] Solution 3

[0120] A compound having formula (VII) (wherein R 1 , R 2 and R 3 As defined for compounds of formula (I) and R 11 is a halide or pseudohalide such as chlorine, bromine, iodine, -OSO2CF3 or -OSO2(CF2)3CF3) can be prepared from a compound having formula (VIII) (wherein R 1 , R 2 and R 3 As defined for compounds of formula (I), R 11 As defined above and R 13 is H or C1-C4 alkyl) is obtained by treating with a suitable base such as sodium methoxide and a formylation agent such as methyl formate, optionally in a suitable solvent (e.g. tetrahydrofuran) to produce a compound of formula (VIIIa) (wherein R 1 , R 2 and R 3 As defined for compounds of formula (I), R 11 As defined above and R 14is H or methyl), followed by methylation with a reagent such as dimethyl sulfate, optionally in the presence of a base such as K2CO3. Alternatively, compounds of formula (VII) can also be obtained directly from compounds of formula (VIII) via treatment with an orthoester such as HC(OMe)3, optionally in the presence of an acid such as H2SO4 or ZnCl2, in a suitable solvent such as methanol. For relevant examples, see: Journal of Agricultural and Food Chemistry, 2007, 55, 5697-5700, Molecules, 2010, 15, 9024-9034 and Organic Process Research and Development, 2015, 19, 639-645. This is shown in Scheme 4.

[0121]

[0122] Solution 4

[0123] A compound having the formula (VIII) (wherein R 1 , R 2 and R 3 As defined for compounds of formula (I), R 11 As defined above and R 13 is H or C1-C4 alkyl) can be obtained by a compound having formula (IX) (wherein R 1 , R 2 and R 3 As defined for compounds of formula (I) and R 11 As defined above) by reacting a base such as K2CO3 and an alkylating agent of formula (X) (wherein R 13 is H or C1-C4 alkyl). Compounds of formula (X) are commercially available or readily prepared from commercially available compounds by standard functional group transformations as described in March's Advanced Organic Chemistry, Smith and March, 6th edition, Wiley, 2007. This is shown in Scheme 5. The skilled person will appreciate that compounds of formula (XI) can be prepared in a similar manner.

[0124]

[0125] Solution 5

[0126] A compound having formula (I) (wherein R 1, R 2 , R 3 and R 4 As defined for compounds of formula (I)) can also be prepared from compounds of formula (XI) wherein R 1 , R 2 , R 3 and R 4 As defined for compounds of formula (I) and R 13 is H or C1-C4 alkyl) is obtained by treating with a base such as sodium methoxide and a formylation agent such as methyl formate to generate a compound of formula (XIa) (wherein R 1 , R 2 , R 3 and R 4 As defined for compounds of formula (I) and R 14 is H or methyl), followed by methylation with a reagent such as dimethyl sulfate in the presence of a base such as K2CO3. Alternatively, compounds of formula (I) can also be obtained directly from compounds of formula (XI) via treatment with an orthoester such as HC(OMe)3, optionally in the presence of an acid such as H2SO4 or ZnCl2, in a suitable solvent such as methanol. For relevant examples, see: Journal of Agricultural and Food Chemistry, 2007, 55, 5697-5700, Molecules, 2010, 15, 9024-9034 and Organic Process Research and Development, 2015, 19, 639-645. This is shown in Scheme 6.

[0127]

[0128] Solution 6

[0129] A compound having the formula (XI) (wherein R 1 , R 2 and R 3 As defined for compounds of formula (I) and R 4 is an optionally substituted cyclopropyl) can be prepared from a compound of formula (XII) (wherein R 1 , R 2 and R 3 As defined for compounds of formula (I) and R 15Representing optionally substituted alkenyl) is prepared by treating with diiodomethane with an organozinc reagent such as diethylzinc, optionally in the presence of an acid source such as trifluoroacetic acid, and in an organic solvent such as dichloromethane. For related examples, see: Organic Reactions, 2001, 58, 1. This is shown in Scheme 7.

[0130]

[0131] Solution 7

[0132] A compound having the formula (XII) (wherein R 1 , R 2 and R 3 As defined for compounds of formula (I), R 15 As defined above and R 13 is H or C1-C4 alkyl) can be obtained by a compound having formula (XIII) (wherein R 1 , R 2 and R 3 As defined for compounds of formula (I) and R 15 As defined above) by reacting a base such as K2CO3 and an alkylating agent of formula (X) (wherein R 13 is H or C1-C4 alkyl). This is shown in Scheme 8. For related examples, see: European Journal of Organic Chemistry, 2015, 2197-2204. Compounds of formula (X) are commercially available or readily prepared from commercially available compounds by standard functional group transformations as described in March's Advanced Organic Chemistry, Smith and March, 6th edition, Wiley, 2007. The skilled person will appreciate that compounds of formula (XI) or formula (VIII) can be prepared in a similar manner.

[0133]

[0134] Solution 8

[0135] A compound having the formula (XIII) (wherein R 1 , R 2 and R 3 As defined for compounds of formula (I) and R 15As defined above) can be reacted via a compound of formula (IX) (wherein R 1 , R 2 and R 3 As defined for compounds of formula (I) and R 11 is a halide or pseudohalide such as chlorine, bromine, iodine, -OSO2CF3 or -OSO2(CF2)3CF3) and a compound having formula (XIV) (wherein R 15 As defined above and M represents a metalloid species or a pseudo-metalloid species (e.g., M includes but is not limited to B(OH)2, BPin, SnBu3) or hydrogen) coupling transformation preparation. For related examples, see: Journal of Medicinal Chemistry [Journal of Medicinal Chemistry], 2015, 58, 9258-9272 and Journal of Medicinal Chemistry [Journal of Medicinal Chemistry], 2014, 57, 1252-1275. This is shown in Scheme 9.

[0136]

[0137] Solution 9

[0138] A compound having the formula (XV) (wherein R 1 , R 2 and R 3 As defined for compounds of formula (I)) can be prepared via a coupling transformation between a compound of formula (XVI) and an optionally substituted C3-C7 cycloolefin in the presence of a suitable acid (e.g. p-toluenesulfonic acid) and in a suitable solvent such as toluene. For relevant examples, see: Journal of Organic Chemistry, 1998, 63, 2858. This is shown in Scheme 10.

[0139]

[0140] Solution 10

[0141] The compound of formula (XV) can be prepared from a compound of formula (XVII) (wherein R 11 The cross-coupling reaction between R (XVIII) and R (XVIII) is obtained by introducing a metal such as lithium or magnesium in a suitable solvent such as toluene or tetrahydrofuran and then introducing R 4-Hal compound and a suitable catalyst complex such as iron(III) chloride. For relevant examples, see: J.Am.Chem.Soc. [Journal of the American Chemical Society] 2004, 126, 3686. This is shown in Scheme 11.

[0142]

[0143] Solution 11

[0144] Compounds of formula (XIX) (wherein E is nitro, chloro, bromo, formyl, or acyl) can be obtained by electrophilic aromatic substitution reactions between compounds of formula (XV) and suitable electrophilic reagents. For relevant examples, see: J. Am. Chem. Soc. [Journal of the American Chemical Society] 1964, 86, 1067 and Adv. Synth. Catal. [Advanced Synthesis and Catalysis] 2010, 352, 3031. This is shown in Scheme 12.

[0145]

[0146] Solution 12

[0147] Alternatively, a compound of formula (IX) wherein R 11 is a halogen, R 4 or R 12 As defined above) can be prepared by a nitro reduction reaction of a compound of formula (XX) in a suitable solvent (e.g. MeOH or ethanol) in the presence of a reducing agent (e.g. hydrogen, ammonium chloride, formic acid or hydrazine) at a temperature between 25°C and 65°C using a metal (e.g. Pd / C, iron or Raney nickel). In some cases, improved reaction performance is obtained when the applied pressure increases. For relevant examples, see: Yoshii, Y. et al. Chem. Commun. (2015), 51, 1070; Takeshiba, H. et al. Eur. Pat. Appl. (1997) 807631. After nitro reduction, a free radical-nucleophilic aromatic substitution reaction (Sandmeyer) of a compound of formula (XXI) is carried out in the presence of a nitrite source (e.g., NaNO or isopentyl nitrite) and a copper source (e.g., CuCN) in an acceptable solvent system such as aqueous acetonitrile at a suitable temperature (e.g., 0° C. to 100° C.). This reaction is shown in Scheme 13.

[0148]

[0149] Solution 13

[0150] The compound of formula (IX) can be prepared from a compound of formula (XXII) (wherein R Y The ester is obtained by a Baeyer-Villiger or Dakin oxidation reaction between H or Me and a suitable oxidant such as peroxyformic acid or hydrogen peroxide. The resulting ester is hydrolyzed to the corresponding phenol. For related examples, see EP2289889. This is shown in Scheme 14.

[0151]

[0152] Solution 14

[0153] Alternatively, a compound of formula (VIII) wherein R 11 is a halogen and R 13 is H or C1-C4 alkyl) can be prepared from a compound of formula (XX) via a nucleophilic aromatic substitution reaction with a compound of formula (XXIII) in the presence of a nitrite source (e.g., NaNO2 or isopentyl nitrite) under acidic conditions (e.g., H2SO4 or HBF4) and a copper source (e.g., CuSO4 or CuCN) in an acceptable solvent system at a suitable temperature (e.g., 0°C to 100°C). Such transformations are described in CN 101580477 or Journal of Iowa Academy of Science 2010, 116, 27-35, and are shown in Scheme 15. The skilled person will appreciate that compounds of formula (XI) or formula (XII) can be prepared in an analogous manner.

[0154]

[0155] Solution 15

[0156] Alternatively, a compound of formula (VIII) wherein R 11 is a halogen and R 13 is H or C1-C4 alkyl) can be prepared from a compound of formula (XXIV) via a nucleophilic aromatic substitution reaction with a compound of formula (XXIII) in the presence of a base (e.g. Cs2CO3), a catalyst (copper source; e.g. CuI or CuO), optionally in the presence of a co-reagent (e.g. 1,10-phenanthroline), in an acceptable solvent system (e.g. toluene) at a suitable temperature (e.g. 0°C to 110°C). Such transformations are described in WO 2007010082 or WO 200837626 and are shown in Scheme 16. The skilled person will appreciate that compounds of formula (XI) or formula (XII) can be prepared in an analogous manner.

[0157]

[0158] Scheme 16

[0159] Functional group interconversions described in the previous schemes are known to those skilled in the art. An extensive list of reaction conditions can be found in: Comprehensive Organic Functional Group Transformations, edited by AR Katritzky, O. Meth-Cohn and C W Rees., Pergamon Press (Elsevier Science Ltd.), Tarrytown, NY 1995; or Comprehensive Organic Transformations: A Guide to Functional Group Preparations, edited by Richard C. Larock, Wiley-VCH, New York 1999.

[0160] If the synthesis results in a mixture of isomers, separation is generally not necessarily necessary, since the individual isomers may in some cases be converted into one another during post-processing for use or during application (e.g. under the action of light, acids or bases). Such conversions may also take place after use, for example in the treated plants, in plant treatment or in the harmful fungi to be controlled.

[0161] As already indicated, it has now been found that the novel compounds of formula (I) according to the invention have a very advantageous level of biological activity for protecting plants against diseases caused by fungi.

[0162] Compounds with formula (I) can be used as active ingredients such as for controlling plant pests in the agricultural sector and related fields of use, or for controlling spoilage microorganisms or potentially harmful organisms to humans on non-living materials. The characteristics of these novel compounds are excellent activity at low application rates, good plant tolerance and environmental safety. They have very useful therapeutic, preventive and systemic characteristics and can be used to protect a lot of cultivated plants. Compounds with formula (I) can be used to suppress or destroy harmful organisms that occur on plants or plant parts (fruits, flowers, leaves, stems, tubers, roots) of a variety of different useful plant crops, while also protecting those plant parts that are grown later, for example, from the infringement of phytopathogenic microorganisms.

[0163] The invention further relates to a method for controlling or preventing infestation of plants or plant propagation materials and / or harvested food crops susceptible to attack by microorganisms by treating the plants or plant propagation materials and / or harvested food crops, wherein an effective amount of a compound of formula (I) is applied to the plants, parts thereof or the locus thereof.

[0164] It is also possible to use compounds of formula (I) as fungicides. As used herein, the term "fungicide" means a compound that controls, modifies or prevents fungal growth. The term "fungicidal effective amount" when used means an amount of such a compound or a combination of such compounds that is capable of producing an effect on fungal growth. Controlling or modifying effects include all deviations from natural development, such as killing, retardation, etc., and prevention includes barriers or other defensive structures in or on plants that prevent fungal infection.

[0165] Compounds with formula (I) can also be used as seed dressings for treating plant propagation materials (e.g., seeds, such as fruits, tubers or cereals) or plant cuttings, for protection against fungal infections together with phytopathogenic fungi present in the soil. Propagation materials can be treated with a composition comprising a compound with formula (I) before planting: for example, seed dressing can be used before sowing. The active compound with formula (I) can also be applied to cereals (coating) by dipping seeds in a liquid formulation or by coating them with a solid formulation. Compositions can also be applied to the planting site when planting propagation materials, for example, to the furrows of seeds during sowing. The invention also relates to such methods for treating plant propagation materials, and to the plant propagation materials so treated.

[0166] In addition, the compounds of formula (I) can be used for controlling fungi in related fields, such as protection of industrial materials (including wood and wood-related industrial products), food storage, and hygiene management.

[0167] Additionally, the present invention can be used to protect non-living materials such as wood, siding and paint from fungal attack.

[0168] The compounds of formula (I) are effective, for example, against fungi and fungal vectors of diseases as well as phytopathogenic bacteria and viruses. These fungi and fungal vectors of diseases as well as phytopathogenic bacteria and viruses are, for example:

[0169] Psoralea corylifolia, Alternaria species, Aphanomyces species, Ascochyta species, Aspergillus species (including A. flavus, A. fumigatus, A. nidulans, A. niger, A. terreus), Acetomyces species (including A. pullulans), Blastomyces dermatitidis, Blumeria graminis, Bremia lactucae, Botrytis species (including B. dothidea, B. obtusa), Botrytis species (including B. cinerea), Candida species (including C. albicans, C. glabrata, C. krusei, C. lusitaniae, C. parapsilosis, C. tropicalis), Cephalosarcina fragrans, Cercosporidium species, Cercospora species (including C.arachidicola), Cercosporidium personatum, Cladosporium species, Claviceps, Coccidioides immitis, Coccidioidomyces species, Colletotrichum species (including C.musae), Cryptococcus neoformans, Diaporthe species, Subsporus species, Endomyces species, Entomophthora species, Epidermophyton species, Erwinia amylovora, Powdery mildew species (including E. cichoracearum), Eutypa lata), Fusarium species (including Fusarium culmorum, Fusarium graminearum, F. langsethiae, Fusarium moniliforme, Fusarium gloeosporium, Fusarium solani, Fusarium oxysporum, Fusarium lamina), Gaeumannomyces graminis, Gibberella fujikuroi, Gloeodes pomigena, Gloeosporium musarum, Glomerella cingulate, Guignardia bidwellii, Gymnosporangium juniperi-virginianae, Helminthosporium species, Camelusporangium species, Histoplasma species (including Histoplasma capsulatum (H.capsulatum), red thread pathogen, Leptographium lindbergi, Leveillulataurica, Lophodermium seditiosum, Microdochium nivale, Microsporum species, Streptoceras species, Mucor species, Mycosphaeria species (including Mycosphaeria graminicola and M. pomi), tree blight pathogen, spruce pathogen, Paracoccidioides species, Penicillium species (including Penicillium digitatum and Penicillium italicum), True mold species, Peronospora species (including Peronospora maize, Peronospora philippinarum and Peronospora kaoliang), Peronospora species, Septoria glume, Phellaria pachyrhizi, Phellinus igniarus, Phyllanthus species, Phoma species, Phomopsis grapevine viticola), Phytophthora species (including Phytophthora infestans), Plasmopara species (including Plasmopara hallii, P. viticola), Grifola species, Pseudocercosporella species (including P. leucotricha), Polymyxa graminis, Polymyxa betae, Pseudocercosporella herpotrichoides, Pseudomonas species, Pseudocercosporella species (including Pseudocercosporella spp., Pseudocercosporella spp.), Pseudopeziza tracheiphila, Downy Mildew species (including barley rust (P.hordei), wheat leaf rust (P.recondita), stripe rust (P.Striiformis), wheat brown rust (P.triticina)), Sclerotinia species, Pyrocoel species, Pyrocoel species (including rice blast fungus (P.oryzae)), Pythium species (including ultimum Pythium), Columnar septum species, Rhizoctonia species, microscopic root Mucor (Rhizomucor pusillus), Rhizopus arrhizus, Rhizosporium species, Trichosporon species (including Scedosporium apical and Scedosporium prolificum), coal spot disease (Schizothyrium pomi), Sclerotinia species, Sclerotium species, Septoria species (including S.nodorum, S.tritici), Sphaerotheca macularis, Sphaerotheca fusca (Sphaerotheca fuliginea), Sporothorix species, Stagonospora nodorum, Stemphylium species. Stereum hirsutum, Thanatephorus cucumeris, Thielaviopsis basicola, Tilletia species, Trichoderma species (including Trichoderma harzianum, Trichoderma pseudokoningii, Trichoderma viride), Trichophyton species, Nuclear Coral Pseudomonas species, Grape hook silk shell, Urocystis species, Ustilago species, Venturia species (including V. inaequalis), Verticillium species, and Xanthomonas species. .

[0170] The compounds of formula (I) can be used, for example, for lawns, ornamental plants such as flowers, shrubs, broad-leaved trees or evergreen plants, such as conifers, as well as tree injection, pest management and the like.

[0171] In the context of the present invention, target crops and / or useful plants to be protected typically include perennial and annual crops, such as berry plants, for example blackberries, blueberries, cranberries, raspberries and strawberries; cereals, for example barley, maize (corn), millet, oats, rice, rye, sorghum, triticale and wheat; fiber plants, for example cotton, flax, jute and sisal; field crops, for example sugar beets and fodder beets, coffee beans, hops, mustard, rapeseed (canola), sugar cane, sunflower, tea and tobacco; fruit trees, for example apples, apricots, avocados, bananas, cherries, citrus, nectarines, peaches, pears and plums; grasses, for example Bermuda grass, bluegrass, bentgrass, centipede grass, fescue, black mulberry; and sorghum. wheatgrass, St. Augustine grass, and zoysia grass; herbs such as basil, borage, chives, cilantro, lavender, lovage, mint, oregano, parsley, rosemary, sage, and thyme; legumes such as beans, lentils, peas, and soybeans; nuts such as almonds, cashews, groundnuts, hazelnuts, peanuts, pecans, pistachios, and walnuts; palm plants such as oil palms; ornamental plants such as flowers, shrubs, and trees; other trees such as cocoa, coconut, olive, and rubber trees; vegetables such as asparagus, eggplant, broccoli, cabbage, carrots, cucumbers, garlic, lettuce, zucchini, melon, okra, onions, peppers, potatoes, squash, rhubarb, spinach, and tomatoes; and vines such as grapes.

[0172] The term "useful plants" is to be understood as also including useful plants which have been rendered tolerant to herbicides such as bromoxynil or classes of herbicides such as, for example, HPPD inhibitors, ALS inhibitors such as primisulfuron, primisulfuron and trifloxysulfuron, EPSPS (5-enol-pyruvate-shikimate-3-phosphate-synthetase) inhibitors, GS (glutamine synthetase) inhibitors or PPO (protoporphyrinogen oxidase) inhibitors as a result of conventional breeding methods or genetic engineering. Examples of crops which have been rendered tolerant to imidazolinones such as imazamox by conventional breeding methods (mutagenesis) are Summer rapeseed (Canola). Examples of crops that have been rendered tolerant to herbicides or herbicides by genetic engineering methods include glyphosate- and glufosinate-resistant corn varieties, which are Herculex and Commercially available under the trade name ANTIQUID®.

[0173] The term "useful plants" is to be understood as also including useful plants which have been transformed by the use of recombinant DNA techniques in such a way that they are able to synthesize one or more selectively acting toxins, as are known, for example, from toxigenic bacteria, in particular those of the genus Bacillus.

[0174] Examples of such plants are: (corn variety expressing CryIA(b) toxin); YieldGard (corn variety expressing CryIIIB(b1) toxin); YieldGard (maize varieties expressing CryIA(b) and CryIIIB(b1) toxins); (corn variety expressing Cry9(c) toxin); Herculex (a corn variety expressing the CryIF(a2) toxin and the enzyme phosphinothricin N-acetyltransferase (PAT) that confers tolerance to the herbicide glufosinate ammonium); NuCOTN (cotton variety expressing CryIA(c) toxin); Bollgard (cotton variety expressing CryIA(c) toxin); Bollgard (cotton varieties expressing CryIA (c) and CryIIA (b) toxins); (cotton varieties expressing VIP toxin); (potato variety, expressing CryIIIA toxin); GT Advantage (GA21 glyphosate tolerance trait), CBAdvantage (Bt11 corn borer (CB) trait), RW (corn rootworm trait) and

[0175] The term "crops" is to be understood as also including crop plants which have been transformed by the use of recombinant DNA techniques in such a way that they are able to synthesize one or more selectively acting toxins, such as are known, for example, from toxigenic bacteria, in particular those of the genus Bacillus.

[0176] Toxins that can be expressed by such transgenic plants include, for example, insecticidal proteins from Bacillus cereus or Bacillus japonicus; or insecticidal proteins from Bacillus thuringiensis, such as delta-endotoxins, for example Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, or Cry9C, or vegetative insecticidal proteins (Vips), for example Vip1, Vip2, Vip3, or Vip3A; or insecticidal proteins of bacterial colonizing nematodes, for example Photorhabdus spp. or Xenorhabdus spp., such as Photorhabdus luminescens, Xenorhabdus nematophila, or Xenorhabdus spp. nematophilus); toxins produced by animals, such as scorpion toxins, spider toxins, bee toxins and other insect-specific neurotoxins; toxins produced by fungi, such as streptomycin, plant lectins, such as pea lectin, barley lectin or snowdrop lectin; lectins; protease inhibitors, such as trypsin inhibitor, silk proteinase inhibitor, potato glycoprotein, cystatin, papain inhibitor; ribosome inactivating protein (RIP), such as ricin, maize-RIP, abrin, luffa seed toxin protein, saporin protein or bryophyllin; steroid metabolizing enzymes, such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glycosyl-transferase, cholesterol oxidase, ecdysone inhibitors, HMG-COA-reductase, ion channel blockers, such as sodium channel or calcium channel blockers, juvenile hormone esterase, diuretic hormone receptor, stilbene synthase, bibenzyl synthase, chitinase and glucanase.

[0177] Further, in the context of the present invention, delta-endotoxins (e.g., Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, or Cry9C) or vegetative insecticidal proteins (Vips) (e.g., Vip1, Vip2, Vip3, or Vip3A) are understood to include, obviously, mixed toxins, truncated toxins, and modified toxins. Mixed toxins are recombinantly produced by new combinations of different domains of those proteins (see, e.g., WO 02 / 15701). Truncated toxins, such as truncated Cry1Ab, are known. In the case of modified toxins, one or more amino acids of the naturally occurring toxin are replaced. In such amino acid replacements, it is preferred that a non-naturally occurring protease recognition sequence is inserted into the toxin, such as, for example, in the case of Cry3A055, a cathepsin-G-recognition sequence is inserted into the Cry3A toxin (see WO 03 / 018810).

[0178] Examples of such toxins or transgenic plants capable of synthesizing such toxins are disclosed in, for example, EP-A-0 374 753, WO 93 / 07278, WO 95 / 34656, EP-A-0 427 529, EP-A-451 878 and WO 03 / 052073.

[0179] Methods for preparing such transgenic plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above. CryI-type deoxyribonucleic acids and their preparation are known, for example, from WO 95 / 34656, EP-A-0 367474, EP-A-0 401 979 and WO 90 / 13651.

[0180] The toxins contained in the transgenic plants render the plants tolerant to harmful insects. Such insects can be found in any insect taxonomic group, but are particularly common among beetles (Coleoptera), two-winged insects (Diptera), and moths (Lepidoptera).

[0181] Transgenic plants containing one or more genes encoding insecticidal resistance and expressing one or more toxins are known and some of them are commercially available. Examples of such plants are: (corn variety expressing Cry1Ab toxin); YieldGard (corn variety expressing Cry3Bb1 toxin); YieldGard (corn varieties expressing Cry1Ab and Cry3Bb1 toxins); (corn variety expressing Cry9C toxin); Herculex (a corn variety expressing the Cry1Fa2 toxin and the enzyme phosphinothricin N-acetyltransferase (PAT) that confers tolerance to the herbicide glufosinate ammonium); NuCOTN (cotton variety expressing Cry1Ac toxin); Bollgard (cotton variety expressing Cry1Ac toxin); Bollgard (cotton varieties expressing Cry1Ac and Cry2Ab toxins); (cotton varieties expressing Vip3A and Cry1Ab toxins); (potato variety, expressing Cry3A toxin); GT Advantage (GA21 glyphosate tolerance trait), CB Advantage (Bt11 corn borer (CB) trait) and

[0182] Further examples of such genetically modified crops are:

[0183] 1. Bt11 corn, from Syngenta Seeds SAS, Chemin del'Hobit 27, F-31 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10. Genetically modified maize, resistant to attack by European corn borer (Ostrinia nubilalis and Sesamia inermis) by transgenic expression of a truncated Cry1Ab toxin. Bt11 corn also transgenic expression of the PAT enzyme to obtain tolerance to the herbicide glufosinate ammonium.

[0184] 2. Bt176 corn, from Syngenta Seeds, 27 Hobbit Road, F-31 790 Saint-Sauveur, France, registration number C / FR / 96 / 05 / 10. Genetically modified maize, resistant to attack by European corn borer (Ostrinia nubilalis and Sesamia inermis) by transgenic expression of Cry1Ab toxin. Bt176 corn also transgenic expression of PAT enzyme to obtain tolerance to the herbicide glufosinate ammonium.

[0185] 3. MIR604 corn, from Syngenta Seeds, 27 Rue Hobbitt, F-31 790 Saint-Sauveur, France, registration number C / FR / 96 / 05 / 10. Corn 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 corn plants is described in WO 03 / 018810.

[0186] 4. MON 863 maize, from Monsanto Europe SA, 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C / DE / 02 / 9. MON 863 expresses the Cry3Bb1 toxin and is resistant to certain coleopteran insects.

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

[0188] 6.1507 maize from Pioneer Overseas Corporation, Avenue Tedesco, 7B-1160 Brussels, Belgium, registration number C / NL / 00 / 10. Genetically modified maize expressing the protein Cry1F for resistance to certain lepidopteran insects and the protein PAT for tolerance to the herbicide glufosinate ammonium.

[0189] 7. NK603×MON 810 maize, from Monsanto Europe, 270-272 Avenue Tervuren, B-1150 Brussels, Belgium, registration number C / GB / 02 / M3 / 03. It is composed of a conventionally bred hybrid maize variety by crossing the genetically modified varieties NK603 and MON 810. NK603×MON 810 maize transgenically expresses the protein CP4 EPSPS obtained from the Agrobacterium strain CP4, which confers resistance to herbicides The strain also expresses the Cry1Ab toxin from Bacillus thuringiensis subsp. kurstakia, which confers tolerance to certain lepidopteran insects, including the European corn borer.

[0190] Compounds of formula (I) (including any one of compounds E.1 to E.23 or F.1 to F.10) or fungicidal compositions according to the present invention comprising compounds of formula (I) can be used to control or prevent phytopathogenic diseases on soybean plants, especially phytopathogenic fungi (such as Psoralea pachyrhizi).

[0191] Specifically, transgenic soybean plants expressing toxins, such as insecticidal proteins such as delta-endotoxins (e.g., Cry1Ac (Cry1Ac Bt protein)). Thus, this can include transgenic soybean plants comprising event MON87701 (see U.S. Pat. No. 8,049,071 and related applications and patents, and WO 2014 / 170327 A1 (see, for example, regarding Intacta RR2PROTM

[008] ) of soybean), event MON87751 (U.S. Patent Application Publication No. 2014 / 0373191) or event DAS-81419 (U.S. Patent No. 8,632,978 and related applications and patents).

[0192] Other transgenic soybean plants may include event SYHT0H2-HPPD tolerance (U.S. Patent Application Publication No. 2014 / 0201860 and related applications and patents), event MON89788-glyphosate tolerance (U.S. Patent Application Publication No. 7,632,985 and related applications and patents), event MON87708-dicamba tolerance (U.S. Patent Application Publication No. US 2011 / 0067134 and related applications and patents), event DP-356043-5-glyphosate and ALS tolerance (U.S. Patent Application Publication No. US2010 / 0184079 and related applications and patents), event A2704-12-glufosinate tolerance (U.S. Patent Application Publication No. US2010 / 0184079 and related applications and patents), event A2704-13-glufosinate tolerance (U.S. Patent Application Publication No. US2010 / 0184079 and related applications and patents), event A2704-20-glufosinate tolerance (U.S. Patent Application Publication No. US2010 / 0184079 and related applications and patents), event A2704-21-glufosinate tolerance (U.S. Patent Application Publication No. US2010 / 0184079 and related applications and patents), event A2704-22-glufosinate tolerance (U.S. Patent Application Publication No. US2010 / 0184079 and related applications and patents), event A2704-23-glufosinate tolerance (U.S. Patent Application Publication No. US2010 / 0184079 and related applications and patents), event A2704-21-glufosinate tolerance (U.S. Patent Application Publication No. US2010 2008 / 0320616 and related applications and patents), event DP-305423-1-ALS tolerance (U.S. Patent Application Publication No. US2008 / 0312082 and related applications and patents), event A5547-127-glufosinate tolerance (U.S. Patent Application Publication No. US 2008 / 0196127 and related applications and patents), event DAS-40278-9-tolerance to 2,4-dichlorophenoxyacetic acid and aryloxyphenoxypropionate (see WO 2011 / 022469, WO 2011 / 022470, WO 2011 / 022471, and related applications and patents), event 127-ALS tolerance (WO 2010 / 080829 and related applications and patents), event GTS 40-3-2 - glyphosate tolerance, event DAS-68416-4-2,4-dichlorophenoxyacetic acid and glufosinate tolerance, event FG72 - glyphosate and isoxathiapiprolin tolerance, event BPS-CV127-9 - ALS tolerance, and GU262 - glufosinate tolerance or event SYHT04R - HPPD tolerance.

[0193] Compounds of formula (I) (including any one of compounds E.1 to E.23 or F.1 to F.10) or fungicidal compositions according to the invention comprising compounds of formula (I) can be used to control or prevent phytopathogenic diseases on soybean plants, especially phytopathogenic fungi (such as pachyrhizopus pachyrhizopus). In particular, there are known in the scientific literature certain superior soybean plant varieties in which R gene stacks conferring a certain degree of immunity or resistance to specific pachyrhizopus pachyrhizopus have been infiltrated into the plant genome, see, for example: "Fighting Asian Soybean Rust", Langenbach C et al., Front Plant Science 7 (797) 2016).

[0194] A superior plant is any plant from a superior line, and thus a superior plant is a representative plant from a superior variety. Non-limiting examples of superior soybean varieties commercially available to farmers or soybean breeders include: AG00802, A0868, AG0902, A1923, AG2403, A2824, A3704, A4324, A5404, AG5903, AG6202, AG0934; AG1435; AG2031; AG2035; AG2433; AG2733; AG2933; AG3334; AG3832; AG4135; AG4632; AG4934; AG5831; AG6534; and AG7231 (Asgrow Seeds, Des Moines, Iowa, USA); BPR0144RR, BPR 4077NRR, and BPR 4390NRR (Bio Plant Research Institute, Inc., Des Moines, Iowa, USA); Plant Research, Camp Point, IL, USA); DKB17-51 and DKB37-51 (DeKalb Genetics, DeKalb, IL, USA); DP 4546RR, and DP 7870RR (Delta & Pine Land Company, Lubbock, TX, USA); JG03R501, JG 32R606C ADD, and JG 55R503C (JGL Inc.), Greencastle, Indiana, USA); NKS13-K2 (NK Division of Syngenta Seeds, Golden Valley, Minnesota, USA); 90M01, 91M30, 92M33, 93M11, 94M30, 95M30, 97B52, P008T22R2; P16T17R2; P22T69R; P25T51R; P34T07R2; P35T58R; P39T67R; P47T36R; P46T21R; and P56T03R2 (Pioneer Hi-Bred International, Inc. Hi-Bred International, Johnston, IA, USA); SG4771NRR and SG5161NRR / STS (Soygenetics, LLC, Lafayette, IN, USA); S00-K5, S11-L2, S28-Y2, S43-B1, S53-A1, S76-L9, S78-G6, S0009-M2; S00 7-Y4; S04-D3; S14-A6; S20-T6; S21-M7; S26-P3; S28-N6; S30-V6; S35-C3; S36-Y6; S39-C4; S47-K5; S48-D9; S52-Y2; S58-Z4; S67-R6; S73-S8; and S78-G6 (Syngenta Seeds, Henderson, KY, USA); Richer (Northstar Seed Ltd., Alberta, Canada); 14RD62 (Stine Seed Co., Iowa, USA); or Armor 4744 (Armor Seed, LLC, Alaska, USA).

[0195] Therefore, in another preferred embodiment, a compound of formula (I) (including any one of compounds E.1 to E.23 or F.1 to F.10) or a fungicidal composition according to the present invention comprising a compound of formula (I) is used to control Psora pachyrhizi (including fungicidal resistant strains thereof, as described below) on elite soybean plant varieties, wherein a stack of R genes conferring a certain degree of immunity or resistance to a specific Psora pachyrhizi has been introgressed in the plant genome. From such use, many benefits can be expected, such as improved biological activity, favorable or broader activity spectrum (including sensitive and resistant strains of Psora pachyrhizi), increased safety, improved crop tolerance, synergistic interactions or enhanced properties, improved onset or longer lasting residual activity, reduction in the number of applications of compounds and compositions required for effective control of plant pathogens (Psora pachyrhizi) and / or reduction in their application rates, thereby achieving beneficial resistance-management practices, reduced environmental impact and reduced operator exposure.

[0196] Fungicidal resistant strains of Phakopsora pachyrhizi have been reported in the scientific literature, where strains resistant to one or more fungicides from at least each of the following fungicidal mode of action classes were observed: sterol demethylation inhibitors (DMIs), quinone outside inhibitors (QoIs), and succinate dehydrogenase inhibitors (SDHIs). See, for example: "Sensitivity of Phakopsora pachyrhizi towards quinone-outside-inhibitors and demethylation-inhibitors, and corresponding resistance mechanisms." Schmitz HK et al., Pest Manag Sci (2014) 70: 378-388; "First detection of a SDH variant with reduced SDHI sensitivity in Phakopsora pachyrhizi" K et al., J Plant Dis Prot (2018) 125:21-2; “Competitive fitness of Phakopsora pachyrhizi isolates with mutations in the CYP51 and CYTB genes.” Klosowski AC et al., Phytopathology (2016) 106:1278-1284; “Detection of the F129L mutation in the cytochrome b gene in Phakopsora pachyrhizi.” Klosowski AC et al., Pest Management Sci (2016) 72:1211-1215.

[0197] Therefore, in a preferred embodiment, a compound of formula (I) (including any one of compounds E.1 to E.23 or F.1 to F.10) or a fungicidal composition according to the present invention comprising a compound of formula (I) is used to control Psoralea pachyrhizi, which is resistant to one or more fungicides from any one of the following fungicidal MoA classes: sterol demethylation inhibitors (DMI), quinone external inhibitors (QoI) and succinate dehydrogenase inhibitors (SDHI).

[0198] As used herein, the term "locus" means a place where or on which plants grow, or where seeds of cultivated plants are sown, or where seeds are to be placed in the soil. It includes soil, seeds, and seedlings, together with established vegetation.

[0199] The term "plant" refers to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, stalks, leaves and fruits.

[0200] The term "plant propagation material" should be understood as meaning the reproductive parts of the plant, such as seeds, which can be used for the propagation of the plant, and vegetative materials, such as cuttings or tubers (e.g., potatoes). For example, seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes and parts of plants can be mentioned. Germinated plants and young plants that will be transplanted after germination or after breaking the ground can also be mentioned. These young plants can be treated completely or partially by dipping and protected before transplanting. Preferably, "plant propagation material" should be understood as meaning seeds.

[0201] Compounds with formula (I) can be used in unmodified form, or preferably, together with conventional adjuvants used in the formulation field. For this purpose, they can be conveniently formulated as emulsifiable concentrates, pastes that can be coated, directly sprayable or dilutable solutions or suspensions, emulsions, wettable powders, soluble powders, dusts, particles and also encapsulations, for example in polymeric materials, in a known manner. For the type of composition, according to the intended purpose and the prevailing environment, application methods are selected, such as spraying, atomizing, dusting, spreading, coating or dumping. These compositions can also contain other adjuvants, such as stabilizers, defoamers, viscosity modifiers, adhesives or tackifiers, together with fertilizers, micronutrient donors or other formulations for obtaining special effects.

[0202] Suitable carriers and adjuvants, for example for agricultural use, can be solid or liquid and are substances useful in formulation technology, for example natural or regenerated mineral substances, solvents, dispersions, wetting agents, tackifiers, thickeners, adhesives or fertilizers. Such carriers are for example described in WO 97 / 33890.

[0203] Suspension concentrates are aqueous formulations in which highly dispersed solid particles of the active compound are suspended. Such formulations include anti-settling agents and dispersants, and may further include wetting agents to enhance activity, as well as defoamers and crystal growth inhibitors. When used, these concentrates are diluted in water and usually applied as a spray to the area to be treated. The amount of active ingredient can range from 0.5% to 95% of the concentrate.

[0204] Wettable powders are in the form of highly dispersed particles that disperse easily in water or other liquid carriers. These particles contain the active ingredient contained in a solid matrix. Typical solid matrices include Fuller's earth, kaolin, silica and other easily wetted organic or inorganic solids. Wettable powders usually contain from 5% to 95% of the active ingredient plus a small amount of a wetting agent, dispersant or emulsifier.

[0205] Emulsifiable concentrates are homogeneous liquid compositions dispersible in water or other liquids and may consist entirely of the active compound and a liquid or solid emulsifier, or may also contain a liquid carrier such as xylene, heavy aromatic naphtha, isophorone and other non-volatile organic solvents. In use, these concentrates are dispersed in water or other liquids and are usually applied as a spray to the area to be treated. The amount of active ingredient may range from 0.5% to 95% of the concentrate.

[0206] Water dispersible granules are dispersed in water or other liquid carriers. These granules contain the active ingredient stored in a solid matrix. Typical solid matrices include fuller's earth, kaolin, silica and other easily wettable organic or inorganic solids. The granules are formed by extrusion, coagulation or spray drying and typically range in diameter from 0.5 mm to 1 cm and preferably 1 to 2 mm. Water dispersible granules typically contain from 5% to 95% active ingredient and may also contain a small amount of wetting agent and / or dispersant.

[0207] Granular formulations include both extrudates and coarser granules and are usually applied undiluted to the area to be treated. Typical carriers for granular formulations include sand, fuller's earth, attapulgite clay, bentonite, montmorillonite, vermiculite, perlite, calcium carbonate, brick, pumice, pyrophyllite, kaolin, dolomite, plaster, wood flour, crushed corn cobs, crushed peanut shells, sugar, sodium chloride, sodium sulfate, sodium silicate, sodium borate, magnesium oxide, mica, iron oxide, zinc oxide, titanium oxide, antimony oxide, cryolite, gypsum, diatomaceous earth, calcium sulfate and other organic or inorganic materials that absorb or are coated with the active compound. Granular formulations usually contain 5% to 25% active ingredients, which may include surfactants such as heavy aromatic volatile oils, kerosene and other petroleum fractions, or vegetable oils; and / or adhesives such as dextrins, glues or synthetic resins.

[0208] Dusts are free-flowing mixtures of the active ingredient with finely divided solids such as talc, clays, flours and other organic and inorganic solids which act as dispersants and carriers.

[0209] Microcapsules are typically droplets or particles of active ingredients encapsulated in an inert porous shell that allows the encapsulated material to escape into the environment at a controlled rate. The diameter of the encapsulated droplets is typically 1 to 50 microns. The encapsulated liquid typically constitutes 50% to 95% of the capsule weight and may include solvents in addition to the active compound. The encapsulated particles are usually porous particles, wherein the porous membrane seals the particle pores, thereby preserving the active species in liquid form inside the particle pores. The diameter of the particles typically ranges from 1 mm to 1 cm and preferably 1 mm to 2 mm. The particles are formed by extrusion, coagulation or spheronization, or are naturally occurring. Examples of such materials are vermiculite, sintered clay, kaolin, attapulgite clay, sawdust and carbon fine particles. Shell or membrane materials include natural and synthetic rubbers, fiber materials, styrene-butadiene copolymers, polyacrylonitrile, polyacrylates, polyesters, polyamides, polyureas, polyurethanes and starch xanthates.

[0210] Other useful formulations for agrochemical applications include simple solutions of the active ingredient in solvents such as acetone, alkylated naphthalenes, xylene and other organic solvents in which the active ingredient is completely soluble at the desired concentration. Pressurized sprays may also be used in which the active ingredient is dispersed in a highly dispersed form due to evaporation of a low-boiling dispersant solvent carrier.

[0211] Suitable agricultural adjuvants and carriers useful for formulating the compositions of the present invention in the above-mentioned formulation types are well known to those of ordinary skill in the art.

[0212] Liquid carriers that can be used include, for example, water, toluene, xylene, naphtha, crop oil, acetone, methyl ethyl ketone, cyclohexanone, acetic anhydride, acetonitrile, acetophenone, amyl acetate, 2-butanone, chlorobenzene, cyclohexane, cyclohexanol, alkyl acetates, diacetone alcohol, 1,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol rosin acid ester, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, N,N-dimethyl 1,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, dipropylene glycol (diproxitol), alkyl pyrrolidone, ethyl acetate, 2-ethylhexanol, ethylene carbonate, 1,1,1-trichloroethane, 2-heptanone, α-pinene, d-limonene, ethylene glycol, ethylene glycol butyl ether, ethylene glycol methyl ether, γ-butyrolactone, glycerol, glycerol diacetate, glycerol mono Acetate, triacetin, hexadecane, hexylene glycol, isoamyl acetate, isobornyl acetate, isooctane, isophorone, cumene, isopropyl myristate, lactic acid, laurylamine, mesityl oxide, methoxypropanol, methyl isoamyl ketone, methyl isobutyl ketone, methyl laurate, methyl octanoate, methyl oleate, dichloromethane, m-xylene, n-hexane, n-octylamine, octadecanoic acid, octylamine acetate, oleic acid, oleylamine, o-xylene, phenol, Polyethylene glycol (PEG400), propionic acid, propylene glycol, propylene glycol monomethyl ether, p-xylene, toluene, triethyl phosphate, triethylene glycol, xylene sulfonic acid, paraffin, mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, methanol, ethanol, isopropanol, and higher molecular weight alcohols such as amyl alcohol, tetrahydrofurfuryl alcohol, hexanol, octanol, ethylene glycol, propylene glycol, glycerol and N-methyl-2-pyrrolidone. Water is generally the carrier of choice for diluting concentrates.

[0213] Suitable solid carriers include, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, kieselguhr, chalk, diatomaxeous earth, lime, calcium carbonate, bentonite, Fuller's earth, cottonseed hulls, wheat flour, soybean flour, pumice, wood flour, walnut shell flour and lignin.

[0214] A wide range of surfactants may be advantageously employed in the liquid and solid compositions, especially those designed to be diluted with a carrier prior to application. These agents, when used, generally constitute from 0.1% to 15% by weight of the formulation. They may be anionic, cationic, nonionic or polymeric in nature and may be employed as emulsifiers, wetting agents, suspending agents or for other purposes. Typical surfactants include alkyl sulfates such as diethanolammonium lauryl sulfate; alkylaryl sulfonates such as calcium dodecylbenzenesulfonate; alkylphenol / alkylene oxide addition products such as nonylphenol-C 18 Ethoxylates; alcohol-alkylene oxide addition products, such as tridecanol-C 16 Ethoxylates; soaps, such as sodium stearate; alkylnaphthalene sulfonates, such as sodium dibutylnaphthalene sulfonate; salts of dialkyl sulfosuccinates, such as sodium di(2-ethylhexyl)sulfosuccinate; sorbitan esters, such as sorbitan oleate; quaternary amines, such as lauryltrimethylammonium chloride; polyoxyethylene esters of fatty acids, such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; and salts of mono- and dialkyl phosphates.

[0215] Other adjuvants commonly used in agricultural compositions include crystallization inhibitors, viscosity modifiers, suspending agents, spray droplet modifiers, pigments, antioxidants, foaming agents, antifoaming agents, opacifiers, compatibilizing agents, defoamers, masking agents, neutralizing and buffering agents, corrosion inhibitors, dyes, flavor enhancers, spreading agents, penetration aids, micronutrients, emollients, lubricants, and fixatives.

[0216] In addition, further, other biocidal active ingredients or compositions can be combined with the composition of the present invention, and used in the method of the present invention and applied simultaneously or sequentially with the composition of the present invention. When applied simultaneously, these other active ingredients can be formulated or mixed in, for example, a spray tank together with the composition of the present invention. These other biocidal active ingredients can be fungicides, herbicides, insecticides, bactericides, acaricides, nematicides and / or plant growth regulators.

[0217] Pesticides referred to herein using their common names are known, for example, from “The Pesticide Manual”, 15th edition, British Crop Protection Council 2009.

[0218] In addition, the compositions of the invention may also be administered with one or more inducers of systemic acquired resistance ("SAR" inducers). SAR inducers are known and described, for example, in U.S. Pat. No. 6,919,298 and include, for example, salicylates and the commercial SAR inducer acibenzolar-S-methyl.

[0219] Compounds of formula (I) are usually used in the form of agrochemical compositions and can be applied to crop areas or crops to be treated simultaneously or sequentially with other compounds. For example, these other compounds can be fertilizers or micronutrient donors or other preparations that affect plant growth. They can also be selective herbicides or non-selective herbicides, together with insecticides, fungicides, bactericides, nematicides, molluscicides or mixtures of several of these preparations, if desired together with other carriers, surfactants or adjuvants commonly used in the formulation field to promote application.

[0220] The compounds of formula (I) can be used in the form of (fungicide) compositions for controlling or protecting against phytopathogenic microorganisms, these compositions comprising at least one compound of formula (I) or at least one preferred individual compound as defined herein as active ingredient (in free form or in the form of an agrochemically usable salt) and at least one of the above-mentioned adjuvants.

[0221] Therefore, the present invention provides a composition comprising at least one compound of formula (I), an agriculturally acceptable carrier and optionally an adjuvant, preferably a fungicidal composition. An agriculturally acceptable carrier is, for example, a carrier suitable for agricultural use. Agricultural carriers are well known in the art. Preferably, in addition to comprising a compound of formula (I), the composition may include at least one or more pesticidal active compounds, such as additional fungicidal active ingredients.

[0222] The compound of formula (I) may be the sole active ingredient of the composition, or it may be admixed with one or more additional active ingredients (such as pesticides, fungicides, synergists, herbicides or plant growth regulators) where appropriate.

[0223] Examples of suitable additional active ingredients include the following: acycloamino acid fungicides, aliphatic nitrogen fungicides, amide fungicides, aniline fungicides, antibiotic fungicides, aromatic fungicides, arsenic-containing fungicides, aryl phenyl ketone fungicides, benzamide fungicides, benzanilide fungicides, benzimidazole fungicides, benzothiazole fungicides, botanical fungicides, bridged biphenyl fungicides, carbamate fungicides, phenylcarbamate 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, organophosphorus fungicides, Organotin fungicides, oxathiin fungicides, oxazole fungicides, benzenesulfamide 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.

[0224] Examples of suitable additional active ingredients also include the following: 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (9-dichloromethylene-1,2,3,4-tetrahydro-1,4-methano-naphthalen-5-yl)-amide, 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid methoxy-[1-methyl-2-(2,4,6-trichlorophenyl)-ethyl]-amide, 1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxylic acid (2-dichloromethylene-3-ethyl-1-methyl-indan-4-yl)-amide (1072957-71-1), 1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxylic acid (4'-methylsulfanyl-biphenyl-2-yl)-amide, 1-methyl -3-difluoromethyl-4H-pyrazole-4-carboxylic acid [2-(2,4-dichloro-phenyl)-2-methoxy-1-methyl-ethyl]-amide, (5-chloro-2,4-dimethyl-pyridin-3-yl)-(2,3,4-trimethoxy-6-methyl-phenyl)-methanone, (5-bromo-4-chloro-2-methoxy-pyridin-3-yl)-(2,3,4-trimethoxy-6-methyl-phenyl)-methanone, 2-{2-[(E)-3-(2,6-dichloro-phenyl)-1-methyl-prop-2-en-(E)-ylideneaminooxymethyl]-phenyl}-2-[(Z)-methoxyimino]-N-methyl-acetamide, 3-[5-(4-chloro-phenyl)-2,3-dimethyl-isoxazolidine-3- yl]-pyridine, (E)-N-methyl-2-[2-(2,5-dimethylphenoxymethyl)phenyl]-2-methoxy-iminoacetamide, 4-bromo-2-cyano-N,N-dimethyl-6-trifluoromethylbenzimidazole-1-sulfonamide, a-[N-(3-chloro-2,6-xylyl)-2-methoxyacetamide]-y-butyrolactone, 4-chloro-2-cyano-N,N-dimethyl-5-p-tolylimidazole-1-sulfonamide, N-allyl-4,5,-dimethyl-2-trimethylsilylthiophene-3-carboxamide, N-(l-cyano-1,2-dimethylpropyl)-2-(2,4-dichlorophenoxy)propionamide, N-(2-methoxy-5-pyridyl)-cyclopropanecarboxamide, (.+-. )-cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-cycloheptanol, 2-(1-tert-butyl)-1-(2-chlorophenyl)-3-(1,2,4-triazol-1-yl)-propan-2-ol, 2',6'-dibromo-2-methyl-4-trifluoromethoxy-4'-trifluoromethyl-1,3-thiazole-5-carboxanilide, 1-imidazolyl-1-(4'-chlorophenoxy)-3,3-dimethylbutan-2-one, (E)-2-[2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate, (E)-2-[2-[6-(2-thioamidophenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate,(E)-2-[2-[6-(2-fluorophenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate, (E)-2-[2-[6-(2,6-difluorophenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate, (E)-2-[2-[3-(pyrimidin-2-yloxy)phenoxy]phenyl]-3-methoxyacrylate, (E)-2-[2-[3-(5-methylpyrimidin-2-yloxy)-phenoxy]phenyl]-3-methoxyacrylate, (E)-2-[2-[3-(phenyl-sulfonyloxy)phenoxy]phenyl-3-methoxyacrylate, (E)-2-[2-[3-(4-nitrophenoxy) )phenoxy]phenyl]-3-methoxyacrylate, methyl (E)-2-[2-phenoxyphenyl]-3-methoxyacrylate, methyl (E)-2-[2-(3,5-dimethyl-benzoyl)pyrrol-1-yl]-3-methoxyacrylate, methyl (E)-2-[2-(3-methoxyphenoxy)phenyl]-3-methoxyacrylate, methyl (E)-2[2-(2-phenylethen-1-yl)-phenyl]-3-methoxyacrylate, methyl (E)-2-[2-(3,5-dichlorophenoxy)pyridin-3-yl]-3-methoxyacrylate, methyl (E)-2-(2-(3-(1,1,2,2-tetrafluoroethoxy)phenoxy)phenyl)-3-methoxyacrylate methyl acrylate, (E)-2-(2-[3-(α-hydroxybenzyl)phenoxy]phenyl)-3-methoxyacrylate, (E)-2-(2-(4-phenoxypyridin-2-yloxy)phenyl)-3-methoxyacrylate, (E)-2-[2-(3-n-propoxy-phenoxy)phenyl]3-methoxyacrylate, (E)-2-[2-(3-isopropoxyphenoxy)phenyl]-3-methoxyacrylate, (E)-2-[2-[3-(2-fluorophenoxy)phenoxy]phenyl]-3-methoxyacrylate, (E)-2-[2-(3-ethoxyphenoxy)phenyl]-3-methoxyacrylate, (E)-2-[2-(4-tert- butyl-pyridin-2-yloxy)phenyl]-3-methoxyacrylate, methyl (E)-2-[2-[3-(3-cyanophenoxy)phenoxy]phenyl]-3-methoxyacrylate, methyl (E)-2-[2-[(3-methyl-pyridin-2-yloxymethyl)phenyl]-3-methoxyacrylate, methyl (E)-2-[2-[6-(2-methyl-phenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate, methyl (E)-2-[2-(5-bromo-pyridin-2-yloxymethyl)phenyl]-3-methoxyacrylate, methyl (E)-2-[2-(3-(3-iodopyridin-2-yloxy)phenoxy)phenyl]-3-methoxyacrylate,(E)-2-[2-[6-(2-chloropyridin-3-yloxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate methyl ester, (E), (E)-2-[2-(5,6-dimethylpyrazin-2-ylmethyloximemethyl)phenyl]-3-methoxyacrylate methyl ester, (E)-2-{2-[6-(6-methylpyridin-2-yloxy)pyrimidin-4-yloxy]phenyl}-3-methoxy-acrylate methyl ester, (E), (E)-2-{2-(3-methoxyphenyl)methyloximemethyl]-phenyl}-3-methoxyacrylate methyl ester, (E)-2-{2-(6-(2-azidophenoxy)-pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate methyl ester, (E), (E) -2-{2-[6-phenylpyrimidin-4-yl)-methyloximemethyl]phenyl}-3-methoxyacrylate, (E), (E)-2-{2-[(4-chlorophenyl)-methyloximemethyl]-phenyl}-3-methoxyacrylate, (E)-2-{2-[6-(2-n-propylphenoxy)-1,3,5-triazin-4-yloxy]phenyl}-3-methoxyacrylate, (E), (E)-2-{2-[(3-nitrophenyl)methyloximemethyl]phenyl}-3-methoxyacrylate, 3-chloro-7-(2-aza-2,7,7-trimethyl-oct-3-ene-5-yne), 2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamide, 3-iodo-2-propane Alkynol, 4-chlorophenyl-3-iodopropargyl formal, 3-bromo-2,3-diiodo-2-propenylethylcarbamate, 2,3,3-triiodoallyl alcohol, 3-bromo-2,3-diiodo-2-propenol, 3-iodo-2-propynyl n-butylcarbamate, 3-iodo-2-propynyl n-hexylcarbamate, 3-iodo-2-propynyl cyclohexylcarbamate, 3-iodo-2-propynyl phenylcarbamate; phenol derivatives such as tribromophenol, tetrachlorophenol, 3-methyl-4-chlorophenol, 3,5-dimethyl-4-chlorophenol, phenoxyethanol, dichlorophenol, o-phenylphenol, m-phenylphenol, p-phenylphenol, 2-benzyl-4-chlorophenol, 5-hydroxy-2(5H)-furanone; 4,5-dichlorodithiazole Linone, 4,5-benzodithiazolinone, 4,5-trimethylenedithiazolinone, 4,5-dichloro-(3H)-1,2-disulfanyl-3-one, 3,5-dimethyl-tetrahydro-1,3,5-thiadiazine-2-thione, N-(2-p-chlorobenzoylethyl)-chlorohexamethylenetetramine, activated ester, acypetacs, cotton bell carbendazim, albendazole, aldimorph, allicin, allyl alcohol, sinozolin, indazolesulfanil, amobam, aminopropylfos, dithiocarb, asomate, aureofungin, azaconazole, azafendin,Azithiram, azoxystrobin, barium polysulfide, bensulfuron, bensulfuron-M, benodanil, benomyl, dichlorvos, bentaluron, benzathiapiprolin, benzathiathionine, benzalkonium chloride, benzamacril, benzamorf, benzohydroxamic acid, benzovindiflupyr, berberine, bethoxazin, biloxazol, binamitraz, biphenyl, biphenyltriazole, bis(dichlorophenoxy)sulfide, bixafen, blasticidin-S, pyridin Bacillus thiocarb, bromothionil, chloranil, ethiopyralid, thiocyanate, butylamine calcium polysulfide, captamipan, captan, morphine, carbendazim, carbendazim hydrochloride, carboxin, carprofen, carvone, CGA41396, CGA41397, mite killer, chitosan, chlobenthiazone, diamine, chloranil, chlorfenapyr, chlorfenapyr, chlorpyrifos, chloropicrin, thiocarb, chlorozolinate, ethiocyanate, climbazole, clotrimazole, clozylacon, copper-containing compounds such as copper acetate, copper carbonate, copper hydroxide, copper naphthenate, copper oleate, copper oxychloride, copper quinoline, copper silicate, copper sulfate, copper resinate, copper zinc chromate and Bordeaux mixture, cresol, thiophene, cuprobam, cuprous oxide, cyazolin, cyclafuramid, cycloheximide, cyfluanid, cymoxanil, cypendazole, cyproconazole, cyproconazole, dazomet, imidacloprid, tin decylphosphide, dehydroacetic acid, di-2-pyridyl disulfide 1,1'-dioxide, dichlofluanid, chloranil, dichloronaphthoquinone, chloranil, dichlorophen, sclerotinol, benzyltriazole, dichlorocyanamide, ethotripsy, difenoconazole, difenoconazole, difluanid, O,O-diisopropyl-S-benzylphosphothioate, dimefluanid ole), sclerotium net, dimetconazole, oxadimethoxine, dimethomorph, dinopenton, dinosulfon, dinoterbon, diphenylamine, bispyribac, dithiocarb, ditalimfos, dithianon, dithiocarb, dodecyl dimethyl ammonium chloride, dodecyl morpholine, dodecin, dodecyl guanidine acetate, dithiocarb, dimethomorph, oxadimethoxine, oxadimethoxine, oxadimethoxine, etem, thiabendazole, ethoxyquin, ethicillin,(Z)-N-Benzyl-N([methyl(methyl-thioethyleneamino-oxycarbonyl)amino]thio)-β-aminopropionic acid ethyl ester, oxadiazine, oxadiazine, imidacloprid, dixon, imidacloprid, chlorfenapyr, fenbuconazole, furamide, fenhexamid, cyanamide, fenpicrol, fenpropidin, fenpropimorph, fenpyraclostrobin, triphenyltin acetate, triphenyltin hydroxide, ferbam, pyrimidine, flutolanil, flumetol, flumorph, flupicolide, fluopyram, fluotrimazole, fluoxastrobin, fluquinconazole, flusilazole, sulfaquinoxaline, flutanil, flutolanil, flutriafol, flu Pyraclostrobin, folpet, formaldehyde, triethyl phosphonate, fosetyl, furalaxyl, forabi, dimethofuran, furconazole, furfural, furanil, furfuran, furanil, griseofulvin, biguanide, halacrinate, hexachlorobenzene, hexachlorobutadiene, hexachlorophene, hexaconazole, hexylthiofos, hydrargaphen, hydroxyisoxazole, oxazolidinone, imazalil, imazalil sulfate, imipenem, biguanide, biguanide triacetate, inezin, iodocarb, ipfentrifluconazole, isoproconazole, isoproconazole, propineb, isoxadiazole Propyl butyl carbamate, pyraclostrobin, pyraclostrobin, isovaledione, izopamfos, kasugamycin, kresoxim-methyl, LY186054, LY211795, LY248908, mancozeb, mancozeb, maneb, o-amide, mecarbinzid, metalaxyl, chlorfluanid, myclobutanil, meprobamate, mercuric chloride, mercurous chloride, meptyldinocap, metalaxyl, metalaxyl-M, mebamoyl, metazoxolone, metconazole, sulfamethoxazole, furazolidone, methyl bromide, methyl iodide, methyl isothiocyanate, metiram, metiram Zinc, fenthiocarb, mefenamic acid, thiocarbamide, milneb, moroxydine, myclozolin, myclozolin, nabam, natamycin, Tianan, nickel fumei, nitrostyrene, phthalocyanine, flufenamic acid, isothiazine, furamide, organic mercury compounds, orysastrobin, osthol, oxadixyl, oxasulfuron, oxathiapiprolin, oxine-copper, oxolinic acid, oxpoconazole, oxycarboxin, paclobutrazol, parinol, pyraclostrobin, penconazole, pencuron,Pentofluanid, pentachlorophenol, penthiopyrad, cyanobacterium methyl, chlorothalonil, phosdiphen, phytomycin-Al, phosphoric acid, phthalide, picoxystrobin, powdery mildew, polycarbamate, polyoxin D, polyoxrim, polyram, allylbenzazole, prochloraz, procymidone, propamidine, propamocarb, propiconazole, propineb, propionic acid, propoxyquin, prothiocarb, prothioconazole, pydiflumetofen, pyraclostrobin, pyraclostrobin, azole Pyrametrostrobin, pyraclostrobin, pyraclostrobin, pyraclostrobin, pyrimidine, pyrimethanil, pyridinitril, pyrimidine, pyrimethanil, pyriofenone, pyroquinone, pyroxychlor, clopidogrel, pyrrolidine, quaternary ammonium compounds, quinacetol, quinazamid, quinconazole, mite-killing agent, quinoxyfen, pentachloronitrobenzene, rabenzazole, santoni n), sedaxane, silthiopyrad, siloxazole, sipconazole, sodium pentachlorophenol, spiroxazoline, streptomycin, sulfur, sultropen, tebuconazole, tebfloquin, chloranthracene, tetrachloronitrobenzene, fosulphur, fluconazole, thiabendazole, thiadifluor, thicyofen, thiofluanid, 2-(thiocyanatomethylthio)benzothiazole, thiophanate-methyl, thioquinox, serene, tiamidazole, timiazole benconazole), tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, triamiphos, triarimol, triazole, imidazobactam, tricyclazole, trimorph, trifloxystrobin, triflumazole, triflumazole, triflumazole, triclopidogrel, triflumazole, urbacide, jinggangmycin, valifenalate, metabactam, vinclozolin, zarilamid, mancozeb, ziram, and zoxamide.

[0225] The compounds of the present invention can also be used in combination with anthelmintics. Such anthelmintics include compounds selected from macrolide compounds, such as ivermectin, avermectin, abamectin, emamectin, eprinomectin, doramectin, selamectin, moxidectin, nemaketin and milbemycin derivatives, as described in EP-357460, EP-444964 and EP-594291. Other anthelmintics include semisynthetic and biosynthetic avermectin / milbemycin derivatives, such as those described in US-5015630, WO-9415944 and WO-9522552. Other anthelmintics include benzimidazoles, such as albendazole, cambendazole, fenbendazole, flubendazole, mebendazole, oxfendazole, oxbendazole, parbendazole and other members of the described class. Additional anthelmintics include imidazothiazoles and tetrahydropyrimidines, such as tetramisole, levamisole, pyrantel pamoate, octadalafil or morantel. Additional anthelmintics include flukeicides (such as triclabendazole and clorsulon) and tapewormicides (such as praziquantel and ethacistel).

[0226] The compounds of the present invention may be used in combination with derivatives and analogs of the paraherquamide / marcfortine class of anthelmintics as well as antiparasitic oxazolines such as those disclosed in US-5478855, US-4639771 and DE-19520936.

[0227] The compounds of the invention can be used in combination with derivatives and analogs of the general class of dioxomorpholine antiparasitic agents as described in WO 96 / 15121 and also with anthelmintic active cyclic depsipeptides such as those described in WO 96 / 11945, WO 93 / 19053, WO 93 / 25543, EP 0 626 375, EP 0 382 173, WO 94 / 19334, EP 0 382 173 and EP 0 503 538.

[0228] The compounds of the present invention can be used in combination with other ectoparasiticides; for example, fipronil; pyrethroids; organophosphates; insect growth regulators such as chlorfenuron; ecdysone agonists such as tebufenozide; neonicotinoids such as imidacloprid, etc.

[0229] The compounds of the present invention may be used in combination with terpene alkaloids, such as those described in International Patent Application Publication Nos. WO 95 / 19363 or WO 04 / 72086, in particular the compounds disclosed therein.

[0230] Other examples of such biologically active compounds that can be used in combination with the compounds of the present invention include, but are not limited to, the following:

[0231] Organophosphates: acephate, methyl pyraclofos, ethyl azinphos-methyl, methyl azinphos-methyl, bromophos, ethyl bromophos, cadusin, chlorethoxyphos, chlorpyrifos, chlorfenapyr, chlormethylphos, demeton, demeton-S-methyl, demeton-S-methyl sulfone, chlormethimide, diazinon, dichlorvos, dicrotophos, dimethoate, ethion, ethion, ethion, oxamethoxam, fenamiphos, fenitrothion, fenthion, fenthion, fenthion, fenthion, pyrifos, fenfothion, anchovy, thiamethoxam, heptenophos, chlorazophos, isopropylphos, isoxazophos, ma Lathion, cypermethrin, methamidophos, methidathion, methyl parathion, mefenphos, monocrotophos, dibromophos, omethoate, methyl oxo-demeton, paraoxon, parathion, methyl parathion, fenthion, phosalone, thiocyanate, phosphine, phosphamidon, phosphamidon, phosphamidon, phosphamidon, phosphamidon, phosphamidon, phosphamidon, phosphamidon, phosphamidon, phosphamidon, phosphamidon, cypermethrin, cypermethrin-methyl, bromophos, pyraclofos, pyridazinphos, quinalphos, thiocarb, thimeton, terbufos, butylpyrimidinphos, stirofosate, thimeton, triazophos, trichlorfon, and chlorpyrifos.

[0232] Carbamates: aldicarb, 2-sec-butylphenyl methyl carbamate, benfuracarb, carbaryl, chlorpyrifos, carbofuran, butylthiocarb, diflubenzuron, ethiofencarb, fenoxycarb, fenthiocarb, furathiocarb, HCN-801, isoprocarb, indoxacarb, methiocarb, methomyl, 5-methyl-m-isopropylphenylbutynyl (methyl) carbamate, cypermethrin, pirimicarb, propoxur, thiodicarb, long-lasting carb, triazolam, UC-51717.

[0233] Pyrethroids: flumethrin, allethrin, cis-cypermethrin, 5-benzyl-3-furylmethyl (E)-(1R)-cis-2,2-dimethyl-3-(2-oxothiolane-3-ylidenemethyl) cyclopropanecarboxylate, bifenthrin, β-cypermethrin, flucythrin, a-cypermethrin, β-cypermethrin, bio-allethrin, bio-allethrin ((S)-cyclopentyl isomer), bio-resmethrin, bifenthrin, NCI-85193, cypermethrin, tri-cyhalothrin Ester, cypermethrin, cypermethrin, deltamethrin, cypermethrin, cypermethrin, esfenvalerate, ether cypermethrin, pentothrin, cypermethrin, cypermethrin, flucythrin, fluvalinate (D isomer), imiprothrin, trifluoroacetic acid, lambda-cyhalothrin, permethrin, phenothrin, prallethrin, pyrethrin (natural product), resmethrin, tetramethrin, transfluthrin, θ-cypermethrin, flutomethrin, t-fluvalinate, tefluthrin, tralomethrin, ζ-cypermethrin.

[0234] Arthropod growth regulators: a) Chitin synthesis inhibitors: benzoyl ureas: chloranil, diflubenzuron, fluazuron, flufenoxuron, flufenoxuron, fluflumuron, lufenuron, diflubenzuron, diflubenzuron, cypermethrin, buprofezin, benzylpyridin, hexathiapiprofen, etoxazole, chlorfentazine; b) Ecdysone antagonists: chlorfenapyr, methoxyfenozide, fenbufenozide; c) Juvenile hormone analogs: pyriproxyfen, methoprene (including S-methoprene), fenoxycarb; d) Lipid biosynthesis inhibitor: spirodiclofen.

[0235] Other antiparasitic drugs: acequinoxaline, amitraz, AKD-1022, ANS-118, azadirachtin, Bacillus thuringiensis, sulfamethoxazole, bifenazate, binacarb, bromocriptine, BTG-504, BTG-505, toxaphene, cartap, dimethoate, chlorfenapyr, chlorfenapyr, chlorfenapyr, chlorfenapyr, chlorfenapyr, chlorfenapyr, clothianidin, cypermethrin, diacloden, cypermethrin, DBI-3204, diclofenac, dihydroxy Methyl dihydroxypyrrolidine, dimethoate, dimethoate, endosulfan, ethiprole, fenpyroxen, flumite, MTI-800, fenpyroximate, pyrimidine, flumethrin, bromothrin, flumethoate, trifluroxyfen, halofenprox, hydrazone, IKI-220, sodium silicate, NC-196, neem guard), nidinorterfuran, nitenpyram, SD-35651, WL-108477, pyridalyl, propargite, protrifenbute, pymetrozine, pyridabenzane, pyrimidine, NC-1111, R-195, RH-0345, RH-2485, RYI-210, S-1283, S-1833, SI-8601, flutoxin, silomadine, spinosad, tebufenpyrad, trichloroacetic acid sulfone, tetracycline, thiacloprid, thiamethoxam, tolfenpyrad, triacetin, triacylglycerol, synergistic acetyl ether, vertalec, YI-5301.

[0236] Biological agents: Bacillus thuringiensis ssp aizawai, Bacillus thuringiensis ssp kurstaki, Bacillus thuringiensis delta endotoxin, baculovirus, insect pathogenic bacteria, viruses and fungi.

[0237] Bactericides: chlortetracycline, oxytetracycline, streptomycin.

[0238] Other biologics: enrofloxacin, febantel, pentoxacillin, meloxicam, cephalexin, kanamycin, pimobendan, clenbuterol, omeprazole, tiamulin, benazepril, pyriprole, cefquinome, florfenicol, buserelin, cefuroxime, tolamectin, ceftiofur, carprofen, mefluazione, praziquantel, triclabendazole.

[0239] Therefore, the compound of formula (I) can be used in combination with one or more other active ingredients to provide various fungicidal mixtures. Specific examples of such mixtures include (where "I" represents a compound of formula (I)): a compound selected from the group consisting of petroleum + I, 1,1-bis (4-chlorophenyl) -2-ethoxyethanol + I, 2,4-dichlorophenylbenzenesulfonate + I, 2-fluoro-N-methyl-N-1-naphthylacetamide + I, 4-chlorophenylphenyl sulfone + I, acetothionil + I, aldicarb + I, sago + I, fruit manphos + I, amine dephosphite + I, amine dephosphite hydrogen oxalate + I, amitraz + I, arsenic trioxide + I, azobenzene + I, azophos + I, benomyl + I, benoxafos + I, benoxafos + I, benzyl alcohol ... Benzyl formate + I, bixafen + I, bromethrin + I, bromofen + I, bromothion + I, bromopyralid + I, buprofezin + I, butanone + I, butanone sulfone + I, butyl pyridaben + I, calcium polysulfide + I, octachlorocamphene + I, chlormethoxam + I, trithion + I, cypermethrin + I, cypermethrin + I, cypermethrin + I, cypermethrin hydrochloride + I, cypermethrin + I, cypermethrin + I, cypermethrin + I, cypermethrin + I, chlormebuform + I, chlormebuform hydrochloride + I, chlormebuform + I, chlormebuform + I, chlormebuform + I, ethyl chlormebuform + I, chlormebuform (chloromebuform) + I, chlormebufen + I, propyl chlormebuform + I, chlormebuform + I, chlormebuform I + I, chlormebuform II + I, chlormebuform + I, closan Tai+I, coumaphos+I, crotamiton+I, batoxon+I, thiophanate+I, fruit insect phosphorus+I, DCPM+I, DDT+I, dinafon+I, dinafon-O+I, dinafon-S+I, demeton-methyl+I, demeton-O+I, demeton-O-methyl+I, demeton-S+I, demeton-S-methyl+I, demeton-S-methyl+I, demeton-S-methyl+I, demeton-S-methyl+I, bacteriostatic+I, dichlorvos+I, dicliphos+I, diclexin+I, methylflox+I, dinex+I, dinex-diclexine+I, Diprofen-4+I, Diprofen-6+I, Orthodiprofen+I, Nitrate+I, Nitrate+I, Nitrate+I, Nitrobutyl+I, Dimethoate+I, Sulfondiphenyl+I, Disulfiram+I, DNOC+I, Dofenapyn+I, Doramectin+I, Indox+I, Eprinomectin+I, Ethiophos+I, Ethiophos+I, Anti-mite+I, Fenbutatin+I, Fenthiocarb+I, Fenpyrad+I, Fenpyrad+I, Fenpyraclostrobin+I, Fentrifanil+I, Fentifanil+I, Fentifanil+I, Fentifanil+I, Fentifanil+I, Fentifanil+I, FMC 1137+I, fenthiocarb+I, fenthiocarb hydrochloride+I, formparanate+I, γ-HCH+I, fenthiocarb+I, benzyl chlorpyrifos+I, hexadecyl cyclopropane carboxylate+I, isothiocarb+I,Jasmine thiocarb I+I, jasmine thiocarb II+I, iodine thiocarb+I, lindane+I, propanil+I, aphidicide+I, dithiophos+I, methylthiophene+I, cypermethrin+I, methyl bromide+I, cypermethrin+I, chlorpyrifos+I, milbemycin+I, propylamine+I, monocrotophos+I, maoguo+I, moxidectin+I, naled+I, 4-chloro-2-(2-chloro-2-methyl-propyl)-5-[(6-iodo-3-pyridyl)methoxy]pyridazine-3-one+I, fluazifop+I, nikkomycin+I, pentamethylenetetracycline+I, pentamethylenetetracycline 1:1 zinc chloride complex+I, omethoate+I, isothiocarb+I, sulfone+I, pp'-DDT+I, parathion+I, permethrin+I, fenthion+I, voltamphos Phosphate+I, thiophanate+I, phosphamidon+I, polychloroterpenes+I, polynactins+I, chloranol+I, cypermethrin+I, propoxur+I, ethidium+I, pyrethrin+I, pyrethrin II+I, pyrethrin+I, pyrimethoxam+I, pyrimethoxam+I, quinalphos+I, quintiofos+I, R-1492+I, glycyrrhizin+I, rotenone+I, octamidine+I, clomiphene+I, selamectin+I, thiophanate+I, SSI-121+I, sulfilamide+I, sulfluramid+I, sulfotep+I, sulfur+I, fluazifop+I I, τ-fluvalinate + I, TEPP + I, tert-butyl carbendazim + I, tetrachlorothiazide sulfone + I, acaricide + I, thiafenox + I, anti-insecticidal carbendazim + I, long-lasting carbendazim + I, methyl thiocarb + I, chlorpyrifos + I, thiamethoxam + I, triazophos + I, triazuron + I, trichloropropoxyphos + I, triamcinol + I, aphidazole + I, vaniliprole + I, bethoxazin + I, copper dioctanoate + I, copper sulfate + I, cybutryne + I, dichloronaphthoquinone + I, dichlorophen + I, endoxan + I, triphenyltin + I, slaked lime + I, sodium mancozeb + I, azoquinone + I, quinone +I, simazine +I, triphenyltin acetate +I, triphenyltin hydroxide +I, yuxu phosphorus +I, piperazine +I, thiophanate +I, chloralose +I, fenthion +I, pyridine-4-amine +I, strychnine +I, 1-hydroxy-1H-pyridine-2-thione +I, 4-(quinoxaline-2-ylamino)benzenesulfonamide +I, 8-hydroxyquinoline sulfate +I, bronopol +I, copper hydroxide +I, cresol +I, dipyrithione +I, dodesine +I, sodium sulfone +I, formaldehyde +I, mercury plus phenanthene +I, kasugamycin +I, kasugamycin hydrochloride hydrate +I, nickel di(dimethyldithiocarbamate) +I, trichloromethylpyridine +I, octhiothione +I, oxolinic acid +I, oxytetracycline +I, hydroxyquinoline potassium sulfate +I, thiabendazole +I,Streptomycin + I, streptomycin sesquisulfate + I, chlorothiazide + I, thimerosal + I, cotton brown banded moth GV + I, radiobacterium + I, Amblyseius spp. + I, celery armyworm NPV + I, Anagrusatomus + I, Aphelinus abdominalis + I, cotton aphid parasitic wasp (Aphidius colemani) + I, Aphidoletes aphidimyza + I, alfalfa silver stripe armyworm NPV + I, Bacillus sphaericus Neide + I, Beauveria brongniartii + I, Chrysoperlacarnea + I, Cryptolaemus montrouzieri+I, codling moth GV+I, Dacnusa sibirica+I, Diglyphus isaea+I, Eretmocerus eremicus+I, Heterorhabditis bacteriophora and H.megidis+I, Hippodamia convergens+I, Leptomastix dactylopii+I, Macrolophus caliginosus+I, Cabbage armyworm NPV+I, Metaphycus helvolus+I, Metarhizium anisopliaevar.acridum)+I, Metarhizium anisopliae var.anisopliae+I, Neodiprion sertifer NPV and N.lecontei NPV+I, Pseudomonas species+I, Paecilomyces fumosoroseus+I, Phytoseiulus persimlis+I, Steinernema bibionis+I, Steinernema carpocapsae+I, Steinernema feltiae+I, Steinernemaglaseri+I,Steinernema riobrave+I, Steinernema riobravis+I, Steinernema scapterisci+I, Steinernema spp.+I, Trichogramma spp.+I, Typhlodromus occidentalis+I, Verticillium lecanii+I, apholanate+I, bisazir+I, busulfan+I, dimatif+I, hemel+I, hempa+I, metepa+I, methiotepa+I, methyl apholanate+I, bis(aziridine) methylaminophosphine sulfide+I, apholate) + I, morzid + I, penfluron + I, tepa + I, thiohempa + I, thiotepa + I, trothamide + I, urethane imine + I, (E)-dec-5-en-1-yl acetate and (E)-dec-5-en-1-ol + I, (E)-tridec-4-en-1-yl acetate + I, (E)-6- Methylhept-2-en-4-ol + I, (E, Z)-tetradec-4,10-dien-1-yl acetate + I, (Z)-dodec-7-en-1-yl acetate + I, (Z)-hexadec-11-enal + I, (Z)-hexadec-11-en-1-yl acetate + I, (Z)-hexadec-13-en-11-yn-1-yl acetate + I, (Z)-eicos-13-en-10-one + I, (Z)-tetradec-7-en-1-al + I 、(Z)-tetradec-9-en-1-ol+I、(Z)-tetradec-9-en-1-yl acetate+I、(7E,9Z)-dodec-7,9-dien-1-yl acetate+I、(9Z,11E)-tetradec-9,11-dien-1-yl acetate+I、(9Z,12E)-tetradec-9,12-dien-1-yl acetate+I、14-methyloctadec-1-ene+I、4-methylnon-5-ol and 4-methylnon-5-one +I, alpha-multistriatin +I, brevicomin +I, codlelure +I, codlemone +I, cuelure +I, disparlure +I, dodec-8-en-1-yl acetate +I, dodec-9-en-1-yl acetate +I,Dodecan-8+I, 10-diene-1-yl acetate+I, dominicalure+I, 4-methyloctanoic acid ethyl ester+I, eugenol+I, southern pine beetle gathering pheromone (frontalin)+I, grandlure+I, grandlure mixture I+I, grandlure mixture II+I, grandlure mixture III+I, grandlure mixture IV+I, hexalure+I, ipsdienol+I, ipsenol+I, japonilure+I, lineatin+I, litlure+I, looplure+I, medlure+I, megatomoic acid+I, methyl ether eugenol + I, muscalure + I, octadecane-2,13-diene-1-yl acetate + I, octadecane-3,13-diene-1-yl acetate + I, orfralure + I, oryctalure + I, ostramone + I, siglure + I, sordidin + I, sulcatol + I, tetradecane-11-ene-1-yl acetate Acetate + I, Mediterranean fruit fly attractant (trimedlure) + I, Mediterranean fruit fly attractant A + I, Mediterranean fruit fly attractant B1 + I, Mediterranean fruit fly attractant B2 + I, Mediterranean fruit fly attractant C + I, trunc-call + I, 2-(octylthio)ethanol + I, butopyronoxyl + I, butoxy (polypropylene glycol) + I, dibutyl adipate + I, dibutyl phthalate + I, dibutyl succinate + I, DEET + I, dimethyl carbate)+I, dimethyl phthalate+I, ethyl hexanediol+I, hexamide+I, methoquin-butyl+I, methylneodecanamide+I, oxamate+I, picaridin+I, 1-dichloro-1-nitroethane+I, 1,1-dichloro-2,2-bis(4-ethylphenyl)ethane+I, 1,2-dichloropropane and 1,3-dichloropropylene+I, 1-bromo-2-chloroethane+I, 2,2,2-trichloro-1-(3,4-dichlorophenyl)ethyl acetate+I, 2,2-dichlorovinyl 2-ethylsulfinylethyl methyl phosphate+I, 2-(1,3-dithiolan-2-yl)phenyl dimethylcarbamate+I, 2-(2-butoxyethoxy)ethyl thiocyanate+I,2-(4,5-dimethyl-1,3-dioxolan-2-yl)phenylmethylcarbamate + 1, 2-(4-chloro-3,5-xylyloxy)ethanol + 1, 2-chlorovinyl diethyl phosphate + 1, 2-imidazolidinone + 1, 2-isovaleryl indan-1,3-dione + 1, 2-methyl (prop-2-ynyl) aminophenylmethylcarbamate + 1, 2-thiocyanatoethyl laurate + 1, 3-bromo-1-chloroprop-1-ene + 1, 3-methyl-1-phenylpyrazol-5-yl dimethylcarbamate + 1, 4- Methyl (prop-2-ynyl) amino-3,5-dimethylphenylmethyl carbamate + I, 5,5-dimethyl-3-oxocyclohex-1-enyl dimethyl carbamate + I, acethion + I, acrylonitrile + I, aldrin + I, aloamicin + I, chloranil + I, α-decandrin + I, aluminum phosphide + I, chloranil + I, neonicotinoid + I, ethyl thiocarb (athidathion) + I, methyl pyrifos + I, Bacillus thuringiensis δ-endotoxin + I, barium hexafluorosilicate + I, barium polysulfide + I, fumonisin + I, Bayer 22 / 190+I, Bayer 22408+I, β-cypermethrin+I, β-cypermethrin+I, bioethanomethrin+I, biopermethrin+I, bis(2-chloroethyl) ether+I, borax+I, bromophenoxyacetate+I, bromo-DDT+I, cypermethrin+I, cypermethrin+I, butathiofos+I, butyl ester+I, calcium arsenate+I, calcium cyanide+I, carbon disulfide+I, carbon tetrachloride+I, badan hydrochloride+I, serva Cevadine + I, Borneol + I, Chlordane + I, Chlordecone + I, Chloroform + I, Chloropicrin + I, Chloronitrile + I, Chlorprazophos + I, Cis-resmethrin + I, Cis-resmethrin + I, Clocythrin + I, Copper acetoarsenite + I, Copper arsenate + I, Copper oleate + I, Coumithoate + I, Cryolite + I, CS 708+I, benzonitrile+I, cypermethrin+I, cypermethrin+I, cypermethrin+I, d-carbofuran+I, DAEP+I, dazomethane+I, decarbofuran+I, diamidafos+I, isochlorphos+I, dimethophos+I, dicresyl+I, cypermethrin+I, dieldrin+I, diethyl 5-methylpyrazol-3-yl phosphate+I, dilor+I, tetrafluoromethylthiocarb+I, dimethoate+I, pyrethrin+I, methyl chlorpyrifos+I, difenocarb+I, propanol+I, pentophenol+I, dinethrin+I, fenthion+I, vegetable phosphorus+I, dithicrofos+I, DSP+I, ecdysterone+I, EI 1642+I,EMPC+I, EPBP+I, etaphos+I, ethiobencarb+I, ethyl formate+I, ethylene dibromide+I, ethylene dichloride+I, ethylene oxide+I, EXD+I, fenethacarb+I, fenethacarb+I, fenoxacrim+I, cypermethrin+I, fenthiophos+I, ethylfenthion+I, flucofuron+I, butylfenthion+I, phosphonium phosphate+I, butylcyclothion+I, furothiocarb+I, pyrethroid+I, biguanide salt+I, biguanide acetate+I, sodium tetrathiocarbonate+I, benzylfenthion+I, HCH+I, HEOD+I, heptachlor+I, cypermethrin+I, HHDN +I, hydrogen cyanide +I, hyquincarb +I, IPSP +I, chlorfenapyr +I, carbofuran +I, isodrin +I, isofenfos +I, isolane +I, rice blast +I, oxathion +I, juvenile hormone I+I, juvenile hormone II+I, juvenile hormone III+I, chlorfenapyr +I, methoprene +I, lead arsenate +I, bromophenylphos +I, lirimfos +I, thiathion +I, m-isopropyl methylcarbamate +I, magnesium phosphide +I, phosphorus azide +I, methyl aphidron +I, chlorpyrifos +I, mercurous chloride +I, methyl sulfoxide +I, metamifos +I, metamifos potassium salt +I, metamifos sodium salt +I, methylsulfonyl fluoride +I, butylene amine +I, methoprene +I, methoxythrin +I, methoxychlor +I, methyl isothiocyanate +I, methyl chloroform +I, dichloromethane +I, anthracene +I, anthelmintic +I, naphthiophos +I, naphthalene +I, NC-170 +I, nicotine +I, nicotine sulfate +I, nithiazine +I, orthonicotine +I, O-5-dichloro-4-iodophenyl O-ethylethyl phosphonothioate +I, O,O-diethyl O-4-methyl-2-oxo-2H-benzopyran-7-yl phosphonothioate +I, O,O-diethyl O-6-methyl-2-propylpyrimidin-4-yl phosphonothioate +I, O,O,O',O'-tetrapropyl dithiodipyrophosphate +I, oleic acid +I, p-dichlorobenzene +I, methyl parathion+I, pentachlorophenol+I, pentachlorophenyl laurate+I, PH60-38+I, fenthion+I, parachlorothion+I, phosphine+I, methyl phoxim+I, pirimetaphos+I, polychlorinated dicyclopentadiene isomers+I, potassium arsenite+I, potassium thiocyanate+I, precocious element I+I, precocious element II+I, precocious element III+I, primidophos+I, profluthrin+I, fenthion+I, pyraclostrobin+I, pyresmethrin+I, quassia extract+I, quinalphos-methyl+I, quinothion+I, iodosamide+I,Resmothrin + I, rotenone + I, thiamethoxam + I, ryanodine + I, sabadilla + I, octamethoxam + I, clostridium + I, SI-0009 + I, thiamethoxam + I, sodium arsenite + I, sodium cyanide + I, sodium fluoride + I, sodium hexafluorosilicate + I, sodium pentachlorophenol + I, sodium selenate + I, sodium thiocyanate + I, sulcofuron + I, sulcofuron-sodium + I, sulfuryl fluoride + I, thiopromide + I, tar + I, thiamethoxam + I, TDE + I, butylpyrimidinphos + I, dimethophos + I, cyclopentylthrin + I, tetrachloroethane + I, thiochlorvos s) + I, cyclohexane + I, cyclohexane oxalate + I, cypermethrin + I, cypermethrin monosodium + I, tralomethrin + I, transpermethrin + I, trichlormetaphos-3 + I, chloranil + I, tolprocarb + I, chlorpyrifos + I, methoxazole + I, veratridine + I, veratridine + I, XMC + I, zetamethrin + I, zinc phosphide + I, zolaprofos + I, and chlorflumethrin + I, tetraflumethrin + I, bis(tributyltin) oxide + I, bromoacetamide + I, iron phosphate + I, niclosamide-ethanolamine + I, Tributyltin oxide + I, pyromorphine + I, snail killer + I, 1,2-dibromo-3-chloropropane + I, 1,3-dichloropropylene + I, 3,4-dichlorotetrahydrothiophene 1,1-dioxide + I, 3-(4-chlorophenyl)-5-methylrhodanine + I, 5-methyl-6-thioxo-1,3,5-thiadiazin-3-yl acetic acid + I, 6-isopentenylaminopurine + I, 2-fluoro-N-(3-methoxyphenyl)-9H-purine-6-amine + I, benclothiaz + I, cytokinin + I, DCIP + I, furfural + I, isamidophos + I, kinetin + I, verrucosporium mycorrhizal composition + I, tetrachlorothiophene + I, xylenol + I , Zeatin + I, Potassium ethyl xanthate + I, Acibenzolar + I, Acibenzolar-S-methyl + I, Polygonum cuspidatum extract + I, α-chlorohydrin + I, Antu + I, Barium carbonate + I, Dimethoate + I, Bromadiolone + I, Bromadiolone + I, Bromadiolone + I, Chlorhexidine + I, Cholecalciferol + I, Chlorodiol + I, Killer + I, Killer naphthalene + I, Killer pyrimidine + I, Killer deke + I, Thiazifop + I, Difacoum + I, Calcifol + I, Flufaxine + I, Fluoroacetamide + I, Flufaxine + I, Flufaxine hydrochloride + I, Felocell + I, Felocell + I, Felocell + I, Felocell + I, Felocell + I, Felocell + I, Felocell + I, Felocell + I, Felocell + I, Felocell + I, Felocell + I, Felocell glycoside + I, Sodium fluoroacetate + I, Thallium sulfate + I, Felocell + I,2-(2-Butoxyethoxy)ethyl piperate + I, 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone + I, farnesol with nerolidol + I, synergistic acetylene ether + I, MGK 264+I, piperonyl butoxide+I, synergistic aldehyde+I, propyl isomer+I, S421+I, synergistic powder+I, sesasmolin+I, sulfoxide+I, anthraquinone+I, copper cyclohexane+I, copper oxychloride+I, dicyclopentadiene+I, serene+I, zinc cyclohexane+I, zinc thiram+I, imanin+I, ribavirin+I, mercuric oxide+I, thiophanate-methyl+I, azaconazole+I, bifenthrin+I, oxadiazole+I, cyproconazole+I, fenpropimorph+I, diniconazole+I, epoxiconazole+I, fenbutazole+I, fluquinconazole+I, fluquinconazole+I, flusilazole+I, flutriafol+I, furopyram+I, hexaconazole+I, imazalil+I, imidoazole+I , picolinazone + I, metconazole + I, myclobutrazol + I, paclobutrazol + I, rice blast ester + I, penconazole + I, prothioconazole + I, pyrifenox + I, prochloraz + I, propiconazole + I, pyraconazole + I, simeconazole + I, tebuconazole + I, fluconazole + I, triadimefon + I, triadimenol + I, fluflumizole + I, trichlorfon + I, pyrimidine + I, chlorfenapyr + I, flufenapyr + I, bupirimate + I, dimethirimol + I, ethirimol + I, dodecacyclic morpholine + I, fenpropidin propidine + I, fenpropimorph + I, spiroxaplanol + I, tridemorph + I, cyprodinil + I, pyraclostrobin + I, pyrimethanil + I, fenpiclonil + I, fludioxonil + I, benalaxyl + I, furalaxyl + I, metalaxyl- + I, R metalaxyl + I, furamide + I, oxadixyl + I, carbendazim + I, debacarb + I, thiabendazole + I, chlozolinate + I, dichlozoline + I, mycobendazole + I, clozoline) + I, procymidone + I, vinclozoline + I, boscalid + I, carboxin + I, furamide + I, flutolanil + I, oxacarb + I, penthiopyrad + I, thiofuran + I, docodine + I, biguanide + I, azoxystrobin + I, enestroburin + I, enestroburin + I, flutolanil + I, flutolanil + I, oxacarb + I, trifloxystrobin + I,Oxystrobin + I, picoxystrobin + I, pyraclostrobin + I, pyraclostrobin + I, ferram + I, mancozeb + I, maneb + ​​I, methanamide + I, methyl propineb + ​​I, maneb + ​​I, captan + I, captan + I, pyraclostrobin + I, folpet + I, tolylfluanid + I, Bordeaux mixture + I, copper oxide + I, mancopper + I, quinoline copper + I, phthalocyanine + I, kefansan + I, isopyruvate + I, chlorpyrifos + I, tolclofos-methyl + I, captan + I, pyraclostrobin + I, blasticidin + I, chloroneb + ​​I, thiophanate-methyl + I, cyfluthrin + I, cymoxanil + I, cyc lobutrifluram+I, diclocymet+I, diclomezine+I, dicloran+I, diethofencarb+I, oxadiazine+I, flumorph+I, dithianon+I, ethaboxam+I, etridiazole+I, oxadiazine+I, imidacloprid+I, pyraclostrobin+I, pyraclostrobin+I, fluazinam+I, sulfaquinoxaline+I, fluopyram+I, fenpyrad+I, fosetyl-aluminum+I, oxadiazine+I, propineb+I, cyazofamid+I, sulfaquinoxaline +I, mefenamic acid ketone +I, pencuron +I, phthalide +I, polyoxins +I, propamocarb +I, pyraclostrobin +I, propoxyquin +I, pyraclostrobin +I, benzathine +I, quinoxyfen +I, pentachloronitrobenzene +I, thiamethoxam +I, imidazolin +I, tricyclazole +I, trifenazone +I, validamycin +I, valeramide +I, benzamide +I, dimethomorph +I, flubeneteram +I, pyraclostrobin +I, fluoxathiapiprolin +I, benzophenone +I, fluoxathiapiprolin +I, fluoxathiapiprolin +I, 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (3',4',5'-trifluoro-biphenyl-2-yl)-amide +I, isofluc ypram+I, isothianidin+I, dipymetitrone+I, 6-ethyl-5,7-dioxo-pyrrolo[4,5][1,4]dithia[1,2-c]isothiazole-3-carbonitrile+I, 2-(difluoromethyl)-N-[3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide+I, 4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyridazine-3-carbonitrile+I, (R)-3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide+I, 4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl)-2,5-dimethyl-pyrazol-3-amine+I,4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine+I, fluindapyr+I, Jiaxiangjunzhi+I, lvbenmixianan+I, dichlobentiazox+I, mandestrobin+I, 3-(4,4-difluoro-3,4-dihydro-3,3-dimethylisoquinolin-1-yl)quinolone+I, 2-[2-fluoro-6-[(8-fluoro-2-methyl-3-quinolyl)oxy]phenyl]propan-2-ol+I, fluorothiazopyrone+I, N-[6-[[[(1-methyltetrazol-5-yl)-phenyl 1-(4-(4,5-dichlorothiazol-2-yl)oxy-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-carboxamidine + 1, 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide + 1, N'-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-carboxamidine + 1, N'-[4-(4,5-dichlorothiazol-2-yl)oxy-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-carboxamidine + 1, [2-[3-[2-[ 1-[2-[3,5-bis(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidinyl]thiazol-4-yl]-4,5-dihydroisoxazol-5-yl]-3-chloro-phenyl] methanesulfonate + I, N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridinyl]carbamic acid but-3-ynyl ester + I, N-[[5-[4-(2,4-dimethylphenyl)triazol-2-yl]-2-methyl-phenyl]methyl]carbamic acid methyl ester + I, 3-chloro-6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine + I, pyridachlometyl + I, 3-(difluoromethyl)-1-methyl-N-[1 ,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide+I, 1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one+I, 1-methyl-4-[3-methyl-2-[[2-methyl-4-(3,4,5-trimethylpyrazol-1-yl)phenoxy]methyl]phenyl]tetrazol-5-one+I, aminopyrifen+I, pyraclostrobin+I, indazolesulfanil+I, fluopyraclostrobin+I, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamine+I, florylpicoxamid+I,Benpyramid + I, isobutylethoxyquinoline + I, ipflufenoquin + I, quinofumelin + I, isoproterenol + I, N-[2-[2,4-dichloro-phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide + I, N-[2-[2-chloro-4-(trifluoromethyl)phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide + I, benzathiostrobin + I, cyanothiostrobin + I, 5-amino-1,3,4-thiadiazole-2-thiol zinc salt (2:1) + I, fluopyram + I, fluthiazolin + I, fluopyram + I, pyrapropoyne + I, pipercaptoethanol oxadiazole (picarbutrazox) + I, 2-(difluoromethyl)-N-(3-ethyl-1,1-dimethyl-indan-4-yl) pyridine-3-carboxamide + I, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylindan-4-yl) pyridine-3-carboxamide + I, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + I, metyltetraprole + I, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylindan-4-yl) pyridine-3-carboxamide + I, α- (1,1-dimethylethyl)-α-[4'-(trifluoromethoxy)[1,1'-biphenyl]-4-yl]-5-pyrimidinemethanol + I, fluoxapiprolin + I, enoxastrobin + I, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + I, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-sulfanyl-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + I, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-sulfanyl-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + I, [(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thioxo-4H-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + I, trinexapac-ethyl + I, syringostyrin + I, zhongshengmycin + I, thiophanate-methyl + I, thiophanate zinc + I, amectotractin + I, iprodione + I; N'-[5-bromo-2-methyl-6-[(1S)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine + I, N'-[5-bromo-2-methyl-6-[(1R)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine + I,N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridinyl]-N-ethyl-N-methyl-formamidine + I, N'-[5-chloro-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridinyl]-N-ethyl-N-methyl-formamidine + I, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridinyl]-N-isopropyl-N-methyl-formamidine + I (these compounds can be prepared from WO 2015 / 155075); N'-[5-bromo-2-methyl-6-(2-propoxypropoxy)-3-pyridinyl]-N-ethyl-N-methyl-formamidine + I (this compound can be prepared by the method described in IPCOM000249876D); N-isopropyl-N'-[5-methoxy-2-methyl-4-(2,2,2-trifluoro-1-hydroxy-1-phenyl-ethyl)phenyl]-N-methyl-formamidine + I, N'-[4-(1-cyclopropyl-2,2,2-trifluoro-1-hydroxy-ethyl)-5-methoxy-2-methyl-phenyl]-N-isopropyl-N-methyl-formamidine + I (these compounds can be prepared by WO 2018 / 228896); N-ethyl-N'-[5-methoxy-2-methyl-4-[2-trifluoromethyl))oxetane-2-yl]phenyl]-N-methyl-formamidine + I, N-ethyl-N'-[5-methoxy-2-methyl-4-[2-trifluoromethyl)tetrahydrofuran-2-yl]phenyl]-N-methyl-formamidine + I (these compounds can be prepared by WO 2019 / 110427); N-[(1R)-1-benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide + I, N-[(1S)-1-benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide + I, N-[(1R)-1-benzyl-3,3,3-trifluoro-1-methyl-propyl]-8-fluoro-quinoline-3-carboxamide + I, N-[(1S)-1-benzyl-3,3,3-trifluoro-1-methyl-propyl]-8-fluoro-quinoline-3-carboxamide + I, N-[(1R)-1-benzyl-3,3,3-trifluoro-1-methyl-propyl]-8-fluoro-quinoline-3-carboxamide + I, -benzyl-1,3-dimethyl-butyl]-7,8-difluoro-quinoline-3-carboxamide + I, N-[(1S)-1-benzyl-1,3-dimethyl-butyl]-7,8-difluoro-quinoline-3-carboxamide + I, 8-fluoro-N-[(1R)-1-[(3-fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide + I, 8-fluoro-N-[(1S)-1-[(3-fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide + I, N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-8-fluoro-quinoline-3-carboxamide + I,N-[(1S)-1-benzyl-1,3-dimethyl-butyl]-8-fluoro-quinoline-3-carboxamide + I, N-((1R)-1-benzyl-3-chloro-1-methyl-but-3-enyl)-8-fluoro-quinoline-3-carboxamide + I, N-((1S)-1-benzyl-3-chloro-1-methyl-but-3-enyl)-8-fluoro-quinoline-3-carboxamide + I (these compounds can be prepared by the method described in WO 2017 / 153380);

[0240] 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline+I, 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,6-trifluoro-3,3-dimethyl-isoquinoline+I, 4,4-difluoro-3,3-dimethyl-1-(6-methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline+I, 4,4-difluoro-3,3-dimethyl-1-(7-methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline+I, 1-(6-chloro-7-methyl-pyrazolo[1,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline+I (these compounds can be prepared by WO 2017 / 025510); 1-(4,5-dimethylbenzimidazol-1-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline + I, 1-(4,5-dimethylbenzimidazol-1-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline + I, 6-chloro-4,4-difluoro-3,3-dimethyl-1-(4-methylbenzimidazol-1-yl)isoquinoline + I, 4,4-difluoro-1-(5-fluoro-4-methyl-benzimidazol-1-yl)-3,3-dimethyl-isoquinoline + I, 3-(4,4-difluoro-3,3-dimethyl-1-isoquinolyl)-7,8-dihydro-6H-cyclopenta[e]benzimidazole + I (these compounds can be prepared by WO 2016 / 156085).N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide + I, N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide + I, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide ]phenyl]methyl]propanamide + I, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea + I, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea + I, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]urea + I, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide + I, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one + I, 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl] 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one+I, 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxylic acid ethyl ester+I, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-1,2,4-triazol-3-amine+I. The compounds in this paragraph can be prepared by the methods described in WO 2017 / 055473, WO 2017 / 055469, WO 2017 / 093348 and WO 2017 / 118689; 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol+I (this compound can be prepared by the method described in WO 2017 / 029179); 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol+I (this compound can be prepared by the method described in WO 2017 / 029179); 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile + I (this compound can be prepared by the method described in WO 2016 / 156290); 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluoro-phenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile + I (this compound can be prepared by the method described in WO 2016 / 156290);2-Amino-6-methyl-pyridine-3-carboxylic acid (4-phenoxyphenyl) methyl ester + I (this compound can be prepared by the method described in WO 2014 / 006945); 2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetraketone + I (this compound can be prepared by the method described in WO 2011 / 138281); N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]thiobenzamide+I; N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide+I; (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide+I (this compound can be prepared by the method described in WO 2018 / 153707); N'-(2-chloro-5-methyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine+I; N'-[2-chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidine+I (this compound can be prepared by the method described in WO 2016 / 202742); 2-(difluoromethyl)-N-[(3S)-3-ethyl l-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide + I (this compound can be prepared by the method described in WO 2014 / 095675); (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone + I, (3-methylisoxazol-5-yl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone + I (these compounds can be prepared by the method described in WO 2-Oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide + I (this compound can be prepared by the method described in WO 2018 / 065414); 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylic acid ethyl ester + I (this compound can be prepared by the method described in WO 2018 / 158365);2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide+I, N-[(E)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide+I, N-[(Z)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide+I, N-[N-methoxy-C-methyl-carbonimide]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide+I (these compounds can be prepared by the method described in WO 2018 / 202428). ;

[0241] The mixing partners described above are known. In the case where the active ingredients are included in "The Pesticide Manual" [The Pesticide Manual-A World Compendium; 13th edition; Editor: CDSTomLin; The British Crop Protection Council], they are described therein by the entry number given in parentheses above for the specific compound; for example the compound "avermectin" is described by the entry number (1). In the case where "[CCN]" is added to the specific compound above, the compound in question is included in the "Compendium of Pesticide Common Names", which can be found on the Internet [A.Wood; Compendium of Pesticide Common Names ,Copyright 1995-2004]; for example, the compound "acetoprole" is described on the Internet at http: / / www.alanwood.net / pesticides / acetoprole.html.

[0242] Most of the above active ingredients are referred to above by so-called "common names", in individual cases the relevant "ISO common name" or another "common name" is used. If a name is not a "common name", the kind of name used is replaced by the name given in parentheses for the specific compound; in this case, the IUPAC name, IUPAC / Chemical Abstracts name, "chemical name", "traditional name", "compound name" or "research code" is used, or if neither one of those names nor the "common name" is used, the "synonym" is used. "CAS Registry Number" means the Chemical Abstracts Registry Number.

[0243] The active ingredient mixture of the compound of formula (I) and the active ingredient as described above is preferably in a mixing ratio of from 100:1 to 1:6000, especially in a ratio of from 50:1 to 1:50, more especially in a ratio of from 20:1 to 1:20, even more especially in a ratio of from 10:1 to 1:10, very especially in a ratio of from 5:1 and 1:5, particularly preferably in a ratio of from 2:1 to 1:2, and a ratio of from 4:1 to 2:1 is likewise preferred, especially a ratio of 1:1, or 5:1, or 5:2, or 5:3, or 5:4, or 4:1, or 4:2 , or 4:3, or 3:1, or 3:2, or 2:1, or 1:5, or 2:5, or 3:5, or 4:5, or 1:4, or 2:4, or 3:4, or 1:3, or 2:3, or 1:2, or 1:600, or 1:300, or 1:150, or 1:35, or 2:35, or 4:35, or 1:75, or 2:75, or 4:75, or 1:6000, or 1:3000, or 1:1500, or 1:350, or 2:350, or 4:350, or 1:750, or 2:750, or 4:750. Those mixing ratios are by weight.

[0244] The mixture as described above can be used in a method for controlling pests, which method comprises applying a composition comprising a mixture as described above to the pests or their environment, except for methods for treating the human or animal body by surgery or therapy and diagnostic methods performed on the human or animal body.

[0245] A mixture comprising a compound of formula (I) and one or more active ingredients as described above can be applied, for example, in a single "water-in-place" form, applied as a combined spray mixture (the mixture is composed of separate formulations of these single active ingredients) (e.g., a "tank mix"), and applied in combination using these separate active ingredients when applied in a sequential manner (i.e., one after another appropriately short period, e.g., a few hours or days). The order of application of the compound of formula (I) and one or more active ingredients as described above is not critical for practicing the present invention.

[0246] The compositions according to the invention may also contain other solid or liquid adjuvants, such as stabilizers, for example non-epoxidized or epoxidized vegetable oils (for example epoxidized coconut oil, rapeseed oil or soybean oil), defoamers (for example silicone oils), preservatives, viscosity regulators, adhesives and / or tackifiers, fertilizers or other active ingredients for obtaining specific effects, such as bactericides, fungicides, nematicides, plant activators, molluscicides or herbicides.

[0247] 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 the solid active ingredient; and in the presence of at least one auxiliary, for example by intimately mixing the active ingredient with one or more auxiliary agents and / or grinding the active ingredient with one or more auxiliary agents. These methods for preparing the compositions and the use of compounds of formula (I) for preparing these compositions are also the subject matter of the present invention.

[0248] Another aspect of the invention relates to the use of a compound of formula (I), or preferably an individual compound as defined herein, a composition comprising at least one compound of formula (I) or at least one preferred individual compound as defined above, or a fungicidal or insecticidal mixture comprising at least one compound of formula (I) or at least one preferred individual compound as defined above mixed with other fungicides or insecticides as described above for controlling or preventing plants, such as useful plants (such as crop plants), their propagation materials (such as seeds), harvested crops (such as harvested food crops), or non-living materials from infestation by insects or phytopathogenic microorganisms, preferably fungal organisms.

[0249] Another aspect of the invention relates to a method for controlling or preventing infestation of plants, for example useful plants (such as crop plants), their propagation materials (such as seeds), harvested crops (such as harvested food crops), or non-living materials by insects or phytopathogenic or spoilage microorganisms or organisms potentially harmful to humans (especially fungal organisms), which method comprises applying a compound of formula (I) or preferably a single compound as defined above as an active ingredient to these plants, parts of these plants or their locus, their propagation materials, or any part of these non-living materials.

[0250] Control or prevention means the reduction of infestation by phytopathogenic or spoilage microorganisms or organisms potentially harmful to humans, especially fungal organisms, to such a level that an improvement is demonstrated.

[0251] The preferred method of controlling or preventing crop plants from being infected by plant pathogenic microorganisms (especially fungal organisms) or insects is foliar application, which includes applying a compound with formula (I) or an agrochemical composition containing at least one of the compounds. Frequency of application and application ratio will depend on the risk of infection by the corresponding pathogen or insect. However, the compound with formula (I) can also be applied to the soil (soil application) by the soil through the root (systemic effect) by soaking the plant in a liquid formulation or by applying the compound in solid form, for example, in a granular form to the soil. In rice crops, such particles can be applied to the paddy field of irrigation. The compound with formula I can also be applied to seeds (coating) in the following manner: the seeds or tubers are impregnated with a liquid formulation of a fungicide, or they are coated with a solid formulation.

[0252] Formulations (e.g. compositions containing a compound of formula (I) and, if desired, solid or liquid adjuvants or monomers for encapsulating the compound of formula (I)) can be prepared in a known manner, typically by intimately mixing and / or grinding the compound with extenders (e.g. solvents, solid carriers and optionally surface-active compounds (surfactants)).

[0253] Advantageous application rates are generally from 5 g to 2 kg of active ingredient (ai) / hectare (ha), preferably from 10 g to 1 kg ai / ha, most preferably from 20 g to 600 g ai / ha. When used as a seed drench, a suitable dosage is from 10 mg to 1 g of active substance / kg seed.

[0254] When the combination according to the invention is used to treat seed, a rate of from 0.001 to 50 g of compound of formula (I) per kg of seed, preferably from 0.01 to 10 g per kg of seed, is generally sufficient.

[0255] Suitably, the composition according to the invention having a compound of formula (I) is administered prophylactically (meaning before the development of the disease) or therapeutically (meaning after the development of the disease).

[0256] The composition of the present invention can be used in any conventional form, for example, in the form of a two-pack, a dry seed treatment powder (DS), a seed treatment emulsion (ES), a seed treatment flowable concentrate (FS), a seed treatment solution (LS), a seed treatment water dispersible powder (WS), a seed treatment capsule suspension (CF), a seed treatment gel (GF), an emulsion concentrate (EC), a suspension concentrate (SC), a suspoemulsion (SE), a capsule suspension (CS), a water-dispersible granule (WG), an emulsifiable granule (EG), an oil-in-water emulsion (EO), an oil-in-water emulsion (EW), a microemulsion (ME), an oil suspension (OD), an oil suspension (OF), an oil-soluble liquid (OL), a soluble concentrate (SL), an ultra-low volume suspension (SU), an ultra-low volume liquid (UL), a concentrate (TK), a dispersible concentrate (DC), a wettable powder (WP) or any technically feasible formulation in combination with an agriculturally acceptable adjuvant.

[0257] Such compositions can be produced in a conventional manner, for example by mixing the active ingredient with an appropriate formulation inert agent (diluent, solvent, filler and optionally other formulation ingredients, such as surfactants, biocides, antifreeze agents, adhesives, thickeners and compounds providing adjuvant effects). Conventional sustained-release formulations intended to last for a long time can also be used. In particular, formulations to be applied in a spray form (such as water-dispersible concentrates (e.g., EC, SC, DC, OD, SE, EW, EO, etc.), wettable powders and granules) can contain surfactants (such as wetting agents and dispersants) and other compounds providing adjuvant effects, such as condensation products of formaldehyde with naphthalene sulfonates, alkyl aryl sulfonates, lignin sulfonates, fatty alkyl sulfates and ethoxylated alkylphenols and ethoxylated fatty alcohols.

[0258] The seed dressing formulation is applied to the seed in a manner known per se using the combination of the invention and the diluent in the form of a suitable seed dressing formulation, for example an aqueous suspension or dry powder having good adhesion to the seed. Such seed dressing formulations are known in the art. The seed dressing formulation may contain a single active ingredient or a combination of active ingredients in encapsulated form, for example as a sustained-release capsule or microcapsule.

[0259] Typically, these formulations include by weight from 0.01% to 90% of an active agent, from 0 to 20% of an agriculturally acceptable surfactant and 10% to 99.99% of a solid or liquid formulation inert agent and one or more adjuvants, the active agent being composed of at least a compound of formula (I) optionally together with other active agents (particularly microbicides or preservatives, etc.). By weight, the concentrated form of the composition typically contains between about 2% and 80%, preferably between about 5% and 70% of the active agent. The application form of the formulation can, for example, contain by weight from 0.01% to 20%, preferably by weight from 0.01% to 5% of the active agent. However, commercial products will preferably be formulated as concentrates, and end users will typically use diluted formulations.

[0260] While it is preferred that commercial products be formulated as concentrates, the end user will generally employ a diluted formulation. DETAILED DESCRIPTION

[0261] Examples

[0262] The following examples illustrate the present invention. The compounds of the present invention may be distinguished from known compounds by greater efficacy at low application rates, which can be demonstrated by one of ordinary skill in the art using the experimental procedures outlined in the examples, using lower application rates (if necessary) such as 60 ppm, 20 ppm or 2 ppm.

[0263] Compounds of formula (I) may have any number of benefits, including, among others, favorable levels of biological activity for protecting plants against diseases caused by fungi or superior properties for use as agrochemical active ingredients (e.g., higher biological activity, favorable activity spectrum, increased safety (including improved crop tolerance), improved physico-chemical properties, or increased biodegradability).

[0264] Throughout this specification, temperatures are given in degrees Celsius and "mp" means melting point. LC / MS means liquid chromatography-mass spectrometry, and a description of the apparatus and methods is as follows:

[0265] Method G:

[0266] Spectra were recorded on a mass spectrometer from Waters (SQD, SQDII single quadrupole mass spectrometer) equipped with an electrospray source (polarity: positive and negative ions, capillary: 3.00 kV, cone range: 30 V, extractor: 2.00 V, source temperature: 150°C, desolvation temperature: 350°C, cone gas flow: 50 l / h, desolvation gas flow: 650 L / h; mass range: 100 to 900 Da) and an Acquity UPLC from Waters: binary pump, heated column compartment, diode array detector and ELSD detector. Column: Waters UPLC HSS T3, 1.8 μm, 30×2.1 mm, temperature: 60°C, DAD wavelength range (nm): 210 to 500, solvent gradient: A = water + 5% MeOH + 0.05% HCOOH, B = acetonitrile + 0.05% HCOOH; gradient: 10%-100% B in 1.2 min; flow rate (mL / min) 0.85

[0267] Method H:

[0268] Spectra were recorded on a mass spectrometer from Waters (SQD, SQDII single quadrupole mass spectrometer) equipped with an electrospray source (polarity: positive and negative, capillary: 3.00 kV, cone range: 30 V, extractor: 2.00 V, source temperature: 150°C, desolvation temperature: 350°C, cone gas flow: 50 L / h, desolvation gas flow: 650 L / h, mass range: 100 Da to 900 Da) and an Acquity UPLC from Waters: binary pump, heated column compartment, diode array detector and ELSD detector. Column: Waters UPLC HSS T3, 1.8 μm, 30×2.1 mm, temperature: 60°C, DAD wavelength range (nm): 210 to 500, solvent gradient: A = water + 5% MeOH + 0.05% HCOOH, B = acetonitrile + 0.05% HCOOH; gradient: 10%-100% B in 2.7 min; flow rate (mL / min) 0.85

[0269] If desired, enantiomerically pure final compounds can be obtained, where appropriate, from racemic materials via standard physical separation techniques (eg, reverse phase chiral chromatography) or by stereoselective synthetic techniques (eg, by using chiral starting materials).

[0270] Preparation Examples

[0271]

[0272] The active ingredient is mixed thoroughly with the adjuvant and the mixture is ground thoroughly in a suitable grinder to provide a wettable powder which can be diluted with water to give a suspension of the desired concentration.

[0273]

[0274]

[0275] The active ingredient is thoroughly mixed with the adjuvant and the mixture is thoroughly ground in a suitable grinder to provide a dust that can be used directly for seed treatment.

[0276] Emulsifiable concentrates

[0277]

[0278] Emulsions of any desired dilution which can be used in plant protection can be obtained from these concentrates by dilution with water.

[0279]

[0280] Ready-to-use dusts are obtained by mixing the active ingredient with a carrier and grinding the mixture in a suitable grinder. Such dusts can also be used for dry seed dressing of seeds.

[0281] Extruded particles

[0282]

[0283] The active ingredient is mixed with the auxiliary and ground, and the mixture is moistened with water. The mixture is extruded and then dried in a stream of air.

[0284] Coated granules Active ingredient [compound of formula (I)] 8%

[0285] Polyethylene glycol (molecular weight 200) 3%

[0286] Kaolin 89%

[0287] The finely ground active ingredient is applied uniformly in a mixer to the kaolin moistened with polyethylene glycol. In this way, dust-free coated granules are obtained.

[0288] Suspension concentrates

[0289]

[0290] The finely ground active ingredient is intimately mixed with adjuvants to give a suspension concentrate from which suspension concentrates of any desired dilution can be obtained by dilution with water. Using such dilutions, living plants together with plant propagation materials can be treated and protected from infection by microorganisms by spraying, pouring or immersion.

[0291] Flowable concentrates for seed treatment

[0292]

[0293] The finely ground active ingredient is intimately mixed with adjuvants to give a suspension concentrate from which suspension concentrates of any desired dilution can be obtained by dilution with water. Using such dilutions, living plants together with plant propagation materials can be treated and protected from infection by microorganisms by spraying, pouring or immersion.

[0294] Extended-release capsule suspension

[0295] 28 parts of the combination of compounds of formula (I) are mixed with 2 parts of an aromatic solvent and 7 parts of a toluene diisocyanate / polymethylene-polyphenyl isocyanate mixture (8:1). This mixture is emulsified in a mixture of 1.2 parts of polyvinyl alcohol, 0.05 parts of a defoamer and 51.6 parts of water until the desired particle size is reached. To this emulsion is added a mixture of 2.8 parts of 1,6-hexanediamine in 5.3 parts of water. The mixture is stirred until the polymerization reaction is complete.

[0296] The obtained capsule suspension is stabilized by adding 0.25 parts of thickener and 3 parts of dispersant. The capsule suspension formulation contains 28% of active ingredient. The diameter of the medium capsule is 8-15 microns.

[0297] The resulting formulation is applied to the seeds as an aqueous suspension in an apparatus suitable for this purpose.

[0298] List of abbreviations:

[0299] Aq.=Water-based

[0300] br s = broad singlet

[0301] ℃ = degrees Celsius

[0302] DCM = dichloromethane

[0303] dd = doublet

[0304] DMF = dimethylformamide

[0305] DMSO = dimethyl sulfoxide

[0306] DMSO-d6 = deuterated dimethyl sulfoxide

[0307] d = doublet

[0308] EtOAc = Ethyl acetate

[0309] equiv. = equivalent

[0310] h = hours

[0311] M = mole

[0312] m = multiplet

[0313] min = minutes

[0314] MHz = Megahertz

[0315] mp = melting point

[0316] Pd2(dba)3 = tris(dibenzylideneacetone)dipalladium(0)

[0317] Pd(dppf)Cl 2· DCM = [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), DCM complex

[0318] Pd(PPh3)2Cl2 = bis(triphenylphosphine)palladium(II) dichloride

[0319] ppm = parts per million

[0320] RT = Room temperature

[0321] R t =Retention time

[0322] s = single peak

[0323] t = triplet

[0324] THF = Tetrahydrofuran

[0325] LC / MS = Liquid Chromatography-Mass Spectrometry (a description of the apparatus and methods for LC / MS analysis is given above)

[0326] X-Phos Pd G2 = Chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II)

[0327] Preparation Example:

[0328] Example 1:This example demonstrates the preparation of (Z)-2-[5-(cyclohexen-1-yl)-2-methyl-phenoxy]-3-methoxy-prop-2-enoic acid methyl ester (Compound F.2 of Table F below):

[0329]

[0330] Step 1: Preparation of methyl 2-(5-bromo-2-methyl-phenoxy)acetate

[0331]

[0332] Potassium carbonate (2 equivalents, 106.9mmol, 14.78g) was added to a solution of 5-bromo-2-methylphenol (53.47mmol, 10.00g) and 2-bromoacetic acid methyl ester (1.5 equivalents, 80.20mmol, 12.27g, 7.44mL) in tetrahydrofuran (0.5mol / L, 106.9mL) at room temperature, and the light brown suspension was heated to 65°C for 2h, then cooled to room temperature overnight. The reaction mixture was diluted with EtOAc and washed with water. The aqueous phase was extracted with EtOAc, and the total combined organic phase was washed with water, brine, dried over Na2SO4, filtered, and concentrated in vacuo to obtain 2-(5-bromo-2-methyl-phenoxy) acetic acid methyl ester (47.22mmol, 15.89g, 88% yield) as a brown liquid. The crude oil was slightly contaminated by residual 2-bromoacetic acid methyl ester, but was directly used in the next step without further purification.

[0333] LCMS (method H), Rt=1.59 min, MS: (M+1)=259,261; 1 H NMR

[0334] (400MHz, CDCl3) δppm 2.25 (s, 3H) 3.84 (s, 3H) 4.66 (s, 2H) 6.84 (d, 1H) 7.05 (m, 2H)

[0335] Step 2: Preparation of (Z)-2-(5-bromo-2-methyl-phenoxy)-3-methoxy-prop-2-enoic acid methyl ester

[0336]

[0337] Part 1: Sodium methoxide (20 equivalents, 161 mmol, 9.13 g) was added in batches to a solution of 2-(5-bromo-2-methylphenoxy)acetate (20.8 g, 80.3 mmol) and methyl formate (6.0 equivalents, 482 mmol, 29.5 g, 30.5 mL) in tetrahydrofuran (0.5 mol / L, 161 mL) at room temperature under argon. The reaction was slightly exothermic and was kept below 30° C. with the help of a room temperature water bath. The reaction mixture was stirred at room temperature for 1 h and quenched by slowly adding a saturated aqueous solution of NaHCO. The two phases were separated and the aqueous phase was extracted with EtOAc. The total combined organic layer was washed with a saturated aqueous solution of NaHCO, brine, dried with NaSO, filtered and concentrated in vacuo to obtain methyl 2-(5-bromo-2-methyl-phenoxy)-3-hydroxy-prop-2-enoate, which was used directly in the next step without further purification.

[0338] LCMS (Method G), Rt = 0.80 and 0.90 min, MS: (M+1) = 287, 289

[0339] Part 2: At room temperature in argon, potassium carbonate (1.5 equivalents, 117mmol, 16.3g) was added to a solution of crude 2-(5-bromo-2-methyl-phenoxy)-3-hydroxy-prop-2-enoic acid methyl esters and dimethyl sulfate (1.2 equivalents, 93.2mmol, 11.8g, 8.8mL) in DMF (0.5mol / L, 155mL), and the reaction mixture was stirred at room temperature for 2h. The reaction mixture was quenched by slowly adding water, and the mixture was extracted with EtOAc. The total organic layer combined was washed with a saturated aqueous solution of NaHCO3, brine, and Na2SO4 was dried, filtered and concentrated in a vacuum. The residue was purified by flash chromatography (cyclohexane: EtOAc) to obtain (Z)-2-(5-bromo-2-methyl-phenoxy)-3-methoxy-prop-2-enoic acid methyl esters (59.6mmol, 18.0g, 75% yield) as an off-white solid.

[0340] LCMS (Method G), Rt=1.02 min, MS: (M+1)=301,303; 1 H NMR

[0341] (400MHz,CDCl 3 )δppm 2.31(s,3H)3.74(s,3H)3.91(s,3H)6.86(d,1H)7.05(m,2H)7.35(s,1H)

[0342] Step 3: Preparation of (Z)-2-[5-(cyclohexen-1-yl)-2-methyl-phenoxy]-3-methoxy-prop-2-enoic acid methyl ester preparation

[0343] To a solution of (Z)-2-(5-bromo-2-methyl-phenoxy)-3-methoxy-prop-2-enoic acid methyl ester (203 mg, 0.67 mmol, 1.00 equiv) in 1,4-dioxane (6 mL) and water (1 mL) was added cyclohexene-1-ylboronic acid (93.4 mg, 0.74 mmol, 1.10 equiv), potassium phosphate (295 mg, 1.35 mmol, 2.00 equiv) and X Phos Pd G2 (53.0 mg, 0.07 mmol, 0.10 equiv). The reaction mixture was stirred at 100 ° C for 15 min and the heat source was removed. After the contents reached room temperature, they were diluted with EtOAc and saturated NaHCO3 aqueous solution and then extracted with EtOAc. All combined organic fractions were washed with saturated NaHCO3 aqueous solution and brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography (cyclohexane:EtOAc) to give (Z)-2-[5-(cyclohexen-1-yl)-2-methyl-phenoxy]-3-methoxy-prop-2-enoic acid methyl ester as an amorphous solid.

[0344] LC-MS (Method G), R t =1.17min,MS:(M+H)=303; 1 H NMR (400MHz, CDCl3) δppm 7.36(s,1H),7.11(d,1H),6.96(dd,1H),6.77(d,1H),6.04(m,1H),3.90(s,3H),3 .74(s,3H),2.36(m,5H),2.17-2.25(m,2H),1.74-1.83(m,2H),1.63-1.71(m,2H).

[0345] Example 2: This example demonstrates the preparation of (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoic acid methyl ester (Compound E.15 in Table E below):

[0346]

[0347] To a solution of (Z)-2-[5-(cyclohexene-1-yl)-2-methyl-phenoxy]-3-methoxy-prop-2-enoic acid methyl ester (132 mg, 0.44 mmol, 1.00 equiv) in hexane (0.87 mL) and EtOAc (2.18 mL) was added palladium on carbon (23.2 mg, 0.01 mmol, 0.02 equiv). The reaction mixture was stirred under a hydrogen atmosphere for 2 days. The reaction mixture was filtered through celite and concentrated in vacuo. The resulting crude residue was purified by flash chromatography (cyclohexane: EtOAc) to give (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoic acid methyl ester (mp: 131° C.-132° C.) as a white solid.

[0348] LC-MS (Method G), R t =1.21min,MS:(M+H)=305; 1 H NMR (400MHz, CDCl3) δppm ppm7.35(s,1H),7.10(d,1H),6.79(dd,1H),6.58(d,1H),3.90(s,3H),3.74(s,3H),2.38-2.4 7(m,1H),2.34(s,3H),1.80-1.89(m,4H),1.75(br,1H),1.33-1.42(m,4H),1.22-1.32(m,1H).

[0349] Example 3: This example demonstrates the preparation of (Z)-2-[5-(2-cyclopropylcyclopropyl)-2-methyl-phenoxy]-3-methoxy-prop-2-enoic acid methyl ester (Compound E.7 of Table E below):

[0350]

[0351] Step 1: Preparation of 5-[(E)-2-cyclopropylvinyl]-2-methyl-phenol

[0352]

[0353] To a solution of 5-bromo-2-methyl-phenol (1.00 g, 5.35 mmol, 1.00 equiv) in DME (26.7 mL) was added 3M aqueous Na2CO3 (5.35 mL, 16.0 mmol, 3 equiv), 2-(2-cyclopropylvinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.33 mL, 6.42 mmol, 1.20 equiv). The reaction mixture was degassed with argon and then Pd(dppf)Cl2.CH2Cl2 (450 mg, 0.54 mmol, 0.10 equiv) was introduced. The black mixture was stirred at 80°C for 2 hours, the heat source was removed and the contents were allowed to return to room temperature, diluted with EtOAc and washed with saturated aqueous NaHCO3 and brine. All combined organic fractions were dried over Na2SO4, filtered and concentrated in vacuo. The resulting crude residue was purified by flash chromatography (cyclohexane:EtOAc) to give 5-[(E)-2-cyclopropylvinyl]-2-methyl-phenol as a reddish technical grade solution (50% purity).

[0354] LC-MS (Method G), R t =1.00min,MS:(M+H)=175; 1 H NMR (400

[0355] MHz, CDCl3)δppm:7.04(d,1H),6.82(dd,1H),6.75(d,1H),6.40(d,1H),5.68(dd,1H) ,4.71(s,1H),2.24(s,3H),1.51-1.63(m,1H),0.79-0.87(m,2H),0.48-0.54(m,2H).

[0356] Step 2: Preparation of methyl 2-[5-[(E)-2-cyclopropylvinyl]-2-methyl-phenoxy]acetate

[0357]

[0358] To an industrial-grade solution of 5-[(E)-2-cyclopropylvinyl]-2-methyl-phenol (purity: 50%, 2.70 g, 7.75 mmol, 1.00 equiv) in DMF (15.5 mL) was added KCO (3.22 g, 23.2 mmol, 3.00 equiv) and methyl bromoacetate (2.44 g, 15.5 mmol, 2.00 equiv). The orange solution was stirred at room temperature for 2 h, diluted with water and extracted with EtOAc. All combined organic fractions were washed with water and brine, dried over NaSO, filtered and concentrated in vacuo. The residue was purified by flash chromatography (cyclohexane: EtOAc) to give methyl 2-[5-[(E)-2-cyclopropylvinyl]-2-methyl-phenoxy] acetate as a brown oil.

[0359] LC-MS (Method G), R t =1.12min,MS:(M+H)=247; 1 H NMR (400

[0360] MHz, CDCl3)δppm:7.08(d,1H),6.88(dd,1H),6.66(d,1H),6.42(d,1H),5.67(dd,1H),4. 67(s,2H),3.83(s,3H),2.28(s,3H),1.59(s,1H),0.80-0.86(m,2H),0.49-0.54(m,2H).

[0361] Step 3: Preparation of methyl 2-[5-(2-cyclopropylcyclopropyl)-2-methyl-phenoxy]acetate

[0362]

[0363] A solution of trifluoroacetic acid (0.41 mL, 5.28 mmol, 4.00 equivalents) in DCM (6.60 mL) was added to a solution of diethylzinc (1 M, 5.30 mL, 5.28 mmol, 4.00 equivalents) cooled to 0 ° C. The reaction mixture was stirred at 0 ° C for 30 min, then a solution of diiodomethane (0.43 mL, 5.28 mmol, 4.00 equivalents) in DCM (2.00 mL) was introduced, and the reaction was stirred at 0 ° C for 30 min. Next, a solution of 2-[5-[(E)-2-cyclopropylvinyl]-2-methyl-phenoxy] methyl acetate (500 mg, 1.32 mmol, 1.00 equivalents) in DCM (2.00 mL) was introduced. The reaction solution was stirred at 0 ° C for 1 h, and then stirred at room temperature for 3 h. Afterwards, the contents were diluted with saturated NH4Cl aqueous solution and extracted with DCM. All combined organic fractions were washed with saturated aqueous NaHCO3 and brine, then dried over Na2SO4, filtered, and concentrated in vacuo. The resulting crude residue was purified by flash chromatography (cyclohexane:EtOAc) to give methyl 2-[5-(2-cyclopropylcyclopropyl)-2-methyl-phenoxy]acetate as a colorless oil.

[0364] LC-MS (Method G), R t =1.17min,MS:(M+H)=261; 1 H NMR (400

[0365] MHz, CDCl3)δppm:7.04-7.06(m,1H),6.59(dd,1H),6.44(d,1H),4.65(s,2H),3.83(s,3H),2.25(s,3H),1. 60-1.67(m,1H),1.06-1.16(m,1H),0.91-0.99(m,1H),0.74(m,2H),0.38-0.48(m,2H),0.11-0.20(m,2H).

[0366] Step 4: Preparation of (Z)-2-[5-(2-cyclopropylcyclopropyl)-2-methyl-phenoxy]-3-hydroxy-prop-2-enoic acid methyl ester preparation

[0367]

[0368] To a solution of NaH (60% in oil, 155 mg, 3.87 mmol, 4.00 equiv) in DMF (2.00 mL) was added methyl 2-[5-(2-cyclopropylcyclopropyl)-2-methyl-phenoxy]acetate (420 mg, 0.97 mmol, 1 equiv) and methyl formate (1.21 mL, 19.4 mmol, 20.0 equiv) in DMF (2.80 mL) at room temperature. The brown reaction mixture was stirred at 35 ° C for 3 h, then slowly diluted with MeOH and water, acidified to pH 2-3, and extracted with EtOAc. All combined organic fractions were washed with water and brine, dried over Na2SO4, filtered and concentrated in vacuo. The resulting crude residue was purified by flash chromatography (cyclohexane:EtOAc) to give (Z)-2-[5-(2-cyclopropylcyclopropyl)-2-methyl-phenoxy]-3-hydroxy-prop-2-enoic acid methyl ester as a brown oil.

[0369] LC-MS (Method G), R t =1.04min,MS:(M+H)=289.

[0370] Step 5: (Z)-2-[5-(2-Cyclopropylcyclopropyl)-2-methyl-phenoxy]-3-methoxy-prop-2-enoic acid methyl ester Preparation

[0371]

[0372] At room temperature to (Z) -2- [5- (2- cyclopropylcyclopropyl) -2- methyl - phenoxy] -3- hydroxy - propyl -2- enoic acid methyl esters (400mg, 0.69mmol, 1.00 equivalent) in DMF (1.40mL) solution add K CO (288mg, 2.08mmol, 3.00 equivalent) and dimethyl sulfate (212mg, 1.66mmol, 2.40 equivalent). The brown solution is stirred at room temperature for 30min, with EtOAc, water and saturated NaHCO The aqueous solution is diluted, and then extracted with EtOAc. All the organic fractions merged are washed with water and salt water, and Na is used SO Drying, filtration and vacuum concentration. The resulting crude residue was purified by flash chromatography (cyclohexane:EtOAc) and by reverse phase chromatography (acetonitrile:water) to give (Z)-2-[5-(2-cyclopropylcyclopropyl)-2-methyl-phenoxy]-3-methoxy-prop-2-enoic acid methyl ester as a white solid (mp: 54-56°C).

[0373] LC-MS (Method G), R t =1.14min,MS:(M+H)=303; 1 H NMR (400

[0374] MHz, CDCl3)δppm:7.33(s,1H),7.03(d,1H),6.57(d,1H),6.44(s,1H),3.89(s,3H),3.73(s,3H),2.31(s,3H),1. 55-1.62(m,1H),1.05-1.13(m,1H),0.90-0.99(m,1H),0.67-0.73(m,2H),0.34-0.47(m,2H),0.07-0.20(m,2H).

[0375] Example 4: This example demonstrates the preparation of (Z)-2-(5-cyclopentyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoic acid methyl ester (Compound E.13 in Table E below):

[0376]

[0377] Under argon atmosphere, 1M THF solution of zinc chloride (2.54mmol) is added in 2M THF solution (2.54mmol) of cyclopentylmagnesium bromide, and light yellow suspension is stirred at room temperature for 10min, and a small exothermic reaction is observed during this period. After this, solution and PdCl of (Z)-2-(5-bromo-2-methyl-phenoxy)-3-methoxy-prop-2-enoic acid methyl esters (0.153g, 0.51mmol) in tetrahydrofuran (2.5mL) are added (dppf) (0.19g, 0.025mmol) and light yellow suspension is heated at 50 ℃ for 3 hours. Then the reaction mixture is made to reach room temperature, quenched with saturated NH4Cl aqueous solution, and extracted with methyl tert-butyl ether. Then the total organic part of merging is washed with water and salt water, dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting crude residue was purified by flash chromatography (cyclohexane:EtOAc gradient) to give 0.106 mg of the title compound as a white solid (mp 80-83° C.).

[0378] LC-MS (Method G), R t =1.16min,MS:(M+H)=291; 1 H NMR(400MHz, CDCl3)δppm:7.35(s,1H),7.09(d,1H),6.82(d,1H),6.60(s,1H),3.90(s,3H),3.72(s,3H) ,2.91(m,1H),2.32(s,3H),2.10-1.97(m,2H),1.85-1.75(m,2H),1.74-1.65(m,2H),1.60-1.45(m,2H).

[0379] Table E: Melting point (mp) data and / or retention time (R) of compounds according to formula (I) t ):

[0380]

[0381]

[0382]

[0383]

[0384] Table F: Melting point (mp) data and / or retention time (R) of compounds according to formula (I) t ):

[0385]

[0386]

[0387]

[0388] Example B: Biological Example / Test Method:

[0389] Alternaria solani (tomato early blight)

[0390] Tomato leaf discs were placed on agar in multiwell plates (24-well format) and sprayed with formulated test compounds diluted in water. 2 days after application, the leaf discs were inoculated with a spore suspension of the fungus. The inoculated leaf discs were incubated in a climate chamber under a light regime of 12 / 12h (light / dark), at 23°C / 21°C (day / night) and 80% rh, and the activity of the compounds was assessed as the percentage of disease control compared to the untreated when appropriate levels of disease damage appeared on the untreated test leaf discs (5-7 days after application).

[0391] The following compounds gave at least 80% control of Alternaria solani at 200 ppm when compared to untreated controls showing extensive disease development under the same conditions:

[0392] (Compounds of Table E): E.13, E.15, E.16, E.20, E.22, E.23

[0393] (Compounds of Table F): F.1, F.7

[0394] Glomerella lagenarium (also Colletotrichum lagenarium) (cucurbit anthracnose):

[0395] Fungal conidia from frozen storage were mixed directly into nutrient broth (PDB potato dextrose broth). DMSO solutions of the test compounds were placed in microtiter plates (96-well format) and the nutrient broth containing the fungal spores was added thereto. These test plates were incubated at 24°C and the inhibition of growth was determined photometrically at 620nm after 72 hours.

[0396] The following compounds at 20 ppm gave at least 80% control of Aspergillus niger when compared to untreated controls which showed extensive disease development under the same conditions:

[0397] (Compounds in Table E): E.3, E.6, E.7, E.9, E.11, E.12, E.13, E.14, E.15, E.16, E.17, E.19, E.20, E.21, E.22, E.23

[0398] (Compounds of Table F): F.1, F.2, F.3, F.4, F.5, F.6, F.7, F.10 Erysiphe graminis f.sp.tritici) (wheat powdery mildew):

[0399] Wheat leaf segments were placed on agar in a multiwell plate (24-well format) and sprayed with the test solution. After drying, the leaf disks were inoculated with fungal spores. After appropriate incubation, the activity of the compound 7 dpi (days after incubation) was assessed as preventive fungicidal activity.

[0400] The following compounds gave at least 80% control of wheat powdery mildew at 200 ppm when compared to untreated controls showing extensive disease development under the same conditions:

[0401] (Compounds in Table E): E.1, E.2, E.3, E.5, E.6, E.7, E.8, E.9, E.10, E.11, E.12, E.13, E.14, E.15, E.16, E.17, E.19, E.20, E.21, E.22, E.23

[0402] (Compounds of Table F): F.1, F.2, F.3, F.4, F.5, F.6, F.7, F.8, F.10

[0403] Monographella nivalis (also Microdochium nivale, Fusarium nivalis (snow mold, root rot of cereals)

[0404] Fungal conidia from frozen storage were mixed directly into nutrient broth (PDB potato dextrose broth). DMSO solutions of the test compounds were placed in microtiter plates (96-well format) and the nutrient broth containing the fungal spores was added thereto. These test plates were incubated at 24°C and the inhibition of growth was determined photometrically at 620nm after 72 hours.

[0405] The following compounds gave at least 80% control of Thielavia nivalis at 20 ppm when compared to untreated controls showing extensive disease development under the same conditions:

[0406] (Compounds in Table E): E.1, E.2, E.3, E.6, E.7, E.8, E.9, E.10, E.11, E.12, E.13, E.14, E.15, E.16, E.17, E.19, E.20, E.21, E.22, E.23

[0407] (Compounds of Table F): F.3, F.4, F.5, F.6, F.7, F.8, F.10 Mycosphaerella arachidis) (also known as Cercospora arachidicola) (peanut brown leaf spot disease)

[0408] Fungal conidia from frozen storage were mixed directly into nutrient broth (PDB potato dextrose broth). DMSO solutions of the test compounds were placed in microtiter plates (96-well format) and the nutrient broth containing the fungal spores was added thereto. These test plates were incubated at 24°C and the inhibition of growth was determined photometrically at 620nm after approximately 5-6 days.

[0409] The following compounds gave at least 80% control of Mycosphaeria arachidis at 20 ppm when compared to untreated controls showing extensive disease development under the same conditions:

[0410] (Compounds in Table E): E.1, E.2, E.3, E.6, E.7, E.8, E.9, E.10, E.11, E.12, E.13, E.14, E.15, E.16, E.17, E.19, E.20, E.21, E.22, E.23

[0411] (Compounds of Table F): F.3, F.4, F.5, F.6, F.7, F.8, F.10 Phakopsora pachyrhizium (soybean rust)

[0412] Soybean leaf disks were placed on agar in a multiwell plate (24-well format) and sprayed with the test solution. After drying, the leaf disks were inoculated with a spore suspension of the fungus. After appropriate incubation, the activity of the compound 12 dpi (days after incubation) was assessed as preventive fungicidal activity.

[0413] The following compounds gave at least 70% control of Phakopsora pachyrhizi at 60 ppm when compared to untreated controls showing extensive disease development under the same conditions:

[0414] (Compounds of Table E): E.12, E.13, E.14, E.15, E.20, E.21

[0415] (Compounds of Table F): F.2, F.3, F.4, F.6

[0416] Phytophthora infestans (late blight of potato / tomato)

[0417] Tomato leaf discs were placed on water agar in a multiwell plate (24-well format) and sprayed with the test solution. After drying, the leaf discs were inoculated with a spore suspension of the fungus. After appropriate incubation, the activity of the compound 4 dpi (days after incubation) was assessed as preventive fungicidal activity.

[0418] The following compounds gave at least 80% control of Phytophthora infestans at 200 ppm when compared to untreated controls which showed extensive disease development under the same conditions:

[0419] (Compounds in Table E): E.2, E.5, E.7, E.9, E.13, E.15, E.16, E.22

[0420] Plasmopara viticola (grape downy mildew):

[0421] Grapevine leaf discs were placed on agar in a multiwell plate (24-well format) and sprayed with the test solution. After drying, the leaf discs were inoculated with a spore suspension of the fungus. After appropriate incubation, the activity of the compound 7 dpi (days after incubation) was assessed as preventive fungicidal activity.

[0422] The following compounds gave at least 80% control of Plasmopara viticola at 200 ppm when compared to untreated controls showing extensive disease development under the same conditions:

[0423] (Compounds in Table E): E.2, E.3, E.5, E.6, E.7, E.8, E.9, E.10, E.11, E.12, E.13, E.14, E.15, E.16, E.19, E.20, E.21, E.22, E.23

[0424] (Compounds of Table F): F.1, F.2, F.3, F.4, F.5, F.6, F.7, F.10 Puccinia reclusa recondita) (brown rust), curative:

[0425] Wheat leaf segments were placed on agar in a multiwell plate (24-well format). The leaf segments were inoculated with a spore suspension of the fungus and sprayed with the test solution 1 day after inoculation. After appropriate incubation, the activity of the compound 8 dpi (days after incubation) was assessed as curative fungicidal activity.

[0426] The following compounds gave at least 80% control of Puccinia reconditatis of wheat at 200 ppm when compared to untreated controls showing extensive disease development under the same conditions:

[0427] (Compounds in Table E): E.7, E.12, E.13, E.15, E.16, E.19, E.20, E.21

[0428] (Compounds of Table F): F.2, F.6, F.7,

[0429] Puccinia recondita (brown rust) of wheat, preventive:

[0430] Wheat leaf segments were placed on agar in a multiwell plate (24-well format) and sprayed with the test solution. After drying, the leaf segments were inoculated with a spore suspension of the fungus. After appropriate incubation, the activity of the compound 8 dpi (days after incubation) was assessed as preventive fungicidal activity.

[0431] The following compounds gave at least 80% control of Puccinia reconditatis of wheat at 200 ppm when compared to untreated controls showing extensive disease development under the same conditions:

[0432] (Compounds in Table E): E.1, E.2, E.3, E.5, E.6, E.7, E.8, E.9, E.10, E.12, E.13, E.14, E.15, E.16, E.19, E.20, E.21, E.22, E.23

[0433] (Compounds of Table F): F.1, F.2, F.3, F.4, F.6, F.7, F.8, F.10 Pyricularia oryzae)

[0434] Rice leaf segments were placed on agar in a multiwell plate (24-well format) and sprayed with the test solution. After drying, the leaf disks were inoculated with a spore suspension of the fungus. After appropriate incubation, the activity of the compound 5 dpi (days after incubation) was assessed as preventive fungicidal activity.

[0435] The following compounds at 200 ppm gave at least 80% control of Magnaporthe oryzae when compared to untreated controls which showed extensive disease development under the same conditions:

[0436] (Compounds in Table E): E.3, E.6, E.7, E.12, E.13, E.15, E.16, E.20, E.21, E.23

[0437] (Compounds of Table F): F.1

[0438] Sclerotinia (cotton rot, white rot, etc.):

[0439] Mycelial fragments of the fungus prepared from fresh liquid culture were mixed directly into nutrient broth (PDB potato dextrose broth). DMSO solutions of the test compounds were placed in microtiter plates (96-well format) and nutrient broth containing fungal spores was added thereto. These test plates were incubated at 24° C. and after 72 hours the inhibition of growth was determined photometrically at 620 nm.

[0440] The following compounds at 60 ppm gave at least 80% control of Sclerotinia sclerotiorum when compared to untreated controls showing extensive disease development under the same conditions:

[0441] (Compounds of Table E): E.7, E.12, E.13, E.22, E.23

[0442] (Compounds of Table F): F.5, F.7

[0443] Comparison data:

[0444] The biological activities of the compounds E.13 and E.15 of the present invention were compared with those of the reference compounds X-1 and X-2. The reference compounds X-1 and X-2 are specifically disclosed on page 16 of WO 98 / 03464 and on page 6 of EP 0 212 859, respectively.

[0445] Example C: Comparative biological activity against Puccinia recondita (brown rust) of wheat, curative:

[0446] Method: Wheat leaf segments were placed on agar in multiwell plates (24-well format). The leaf segments were inoculated with a spore suspension of the fungus and sprayed with the test solution 1 day after inoculation. After appropriate incubation, the activity of the compound 8 dpi (days after incubation) was assessed as curative fungicidal activity.

[0447] The data are presented as percent disease control for each compound and test rate in the biological assays described in Table H below.

[0448] Table H - Biological activity against Puccinia recondita (brown rust) of wheat, curative:

[0449]

[0450] Example D: Comparative biological activity against Phakopsora pachyrhizi (soybean rust):

[0451] Method: Soybean plants were sprayed in a spray chamber with formulated DMSO compound solutions diluted to appropriate concentrations with 0.1% OCHIMA (adjuvant containing polyethoxylated sorbitan hexaoleate and tri(2-ethylhexyl)phosphate) just before spraying. One day after application, leaf disks were cut from the treated plants and placed on agar in 24-well plates. Thereafter, the leaf disks were inoculated with a spore suspension of the fungus. After appropriate incubation, the activity of the compounds 12 dpi (days after incubation) was assessed as preventive fungicidal activity.

[0452] The data are presented as percent disease control for each compound and test rate in the biological assays described in Table 1 below.

[0453] Table I - Biological activity against Phakopsora pachyrhizi (soybean rust):

[0454]

[0455] Example E: Comparative biological activity against Phakopsora pachyrhizi (soybean rust):

[0456] Method: The compound to be tested was prepared as a DMSO solution, which was diluted to the appropriate concentration with 0.025% Tween20 just before spraying. Soybean leaf discs were placed on agar in a multiwell plate (24-well format) and sprayed with the test solution. After drying, the leaf discs were inoculated with a spore suspension of the fungus. After appropriate incubation, the activity of the compound 12 dpi (days after incubation) was assessed as preventive fungicidal activity.

[0457] The data are presented as percent disease control for each compound and test rate in the biological assays described in Table J below.

[0458] Table J - Biological activity against Phakopsora pachyrhizi (soybean rust):

[0459]

Claims

1. An intermediate having formula (XIb) in R 1 It is methyl; R 2 It is hydrogen; R 3 It is hydrogen; R 4 is selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl; and R 13 It is H or C1-C4 alkyl.

2. An intermediate having formula (XIc) in R 1 It is methyl; R 2 It is hydrogen; R 3 It is hydrogen; R 4 is selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl; and R 14 It is H or C1-C4 alkyl.

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