Kills microbial inducers

Abstract

The compounds of formula (I) are useful as pesticides, particularly as bactericides and fungicides. [Formula 1] TIFF2023529631000026.tif67155 (wherein the substituents are as defined in claim 1) Compound.

Description

[Technical Field]

[0001] The present invention relates, for example, to microbial thiazole derivatives as active ingredients having microbial activity, particularly bactericidal and fungicidal activity. The present invention also relates to the preparation of these thiazole derivatives, to pesticide compositions comprising at least one thiazole derivative, and to the use of thiazole derivatives or compositions thereof in agriculture or horticulture for controlling or preventing ectoparasitism of plants, harvested food crops, seeds, or non-biological substances by plant pathogenic microorganisms, preferably fungi. [Background technology]

[0002] International Publication Nos. 2010 / 012793 and 2017 / 207362 describe thiazole derivatives as biological agents. [Overview of the project] [Means for solving the problem]

[0003] According to the present invention, formula (I): [ka] (In the formula, A is either CH or N; R 1 These are C1-C4 alkoxy C1-C2 alkyl, C1-C6 alkylsulfanyl C1-C6 alkyl, C1-C6 alkylsulfinyl C1-C6 alkyl, C1-C6 alkylsulfonyl C1-C6 alkyl, or heterocyclyl, where the heterocyclyl portion is a 4-membered, 5-membered, or 6-membered non-aromatic monocyclic ring containing 1, 2, or 3 heteroatoms individually selected from nitrogen, oxygen, and sulfur; R 2 is hydrogen or halogen; R 3 These are C1-C8 alkyl groups; R 4 , R 5 , R 6 Each of these is independently either hydrogen or a C1-C4 alkyl group; R7 These are hydrogen, C1-C4 alkyl, C1-C6 alkoxycarbonyl, or C1-C6 alkoxy; R 8 (These are hydrogen, C1-C6 alkoxy C1-C6 alkylcarbonyl, C1-C6 alkylsulfanyl C1-C6 alkylcarbonyl, C1-C6 alkylsulfinyl C1-C6 alkylcarbonyl, C1-C6 alkylsulfonyl C1-C6 alkylcarbonyl, or heterocyclylcarbonyl, where the heterocyclyl portion is a 4-membered, 5-membered, or 6-membered non-aromatic monocyclic ring containing 1, 2, or 3 heteroatoms individually selected from nitrogen, oxygen, and sulfur.) A compound or a salt or N-oxide thereof is provided.

[0004] According to a second aspect of the present invention, an agricultural composition is provided comprising a bactericidal and fungicidal amount of the compound of formula (I) according to the present invention. Such an agricultural composition may further comprise at least one additional active ingredient and / or an agriculturally acceptable diluent or carrier.

[0005] A third aspect of the present invention provides a method for controlling or preventing ectoparasitism of useful plants by plant pathogenic microorganisms, wherein a bactericidal and fungicidal amount of the compound of formula (I) or a composition containing this compound as an active ingredient is applied to the plant, a part thereof, or its habitat.

[0006] According to a fourth aspect of the present invention, the use of a compound of formula (I) as a bactericidal and fungicidal agent is provided. According to this particular aspect of the present invention, the use may or may not include methods for the treatment of the human or animal body by surgery or therapy. [Modes for carrying out the invention]

[0007] As used herein, the term "halogen" refers to fluorine (fluoro), chlorine (chloro), bromine (bromo), or iodine (iod).

[0008] As used herein, the term "C1-C8 alkyl" refers to a straight-chain or branched-chain hydrocarbon chain group composed of only carbon and hydrogen atoms, containing no unsaturation, having 1 to 8 carbon atoms, and being bonded to the remainder of the molecule by a single bond. "C1-C6 alkyl", "C1-C4 alkyl" and "C1-C3 alkyl" should be construed accordingly. Examples of C1-C8 alkyl include, but are not limited to, methyl, ethyl, n-propyl and their isomers, such as iso-propyl. The "C1-C6 alkylene" group refers to the corresponding definition of C1-C6 alkyl, except that the group is bonded to the remainder of the molecule by two single bonds.

[0009] As used herein, the term "C1-C6 alkoxy" refers to a group of the formula -OR a where R is generally a C1-C6 alkyl group as defined above. The terms "C1-C4 alkoxy" and "C1-C3 alkoxy" should be construed accordingly. Examples of C1-C6 alkoxy include, but are not limited to, methoxy, ethoxy, 1-methoxyethoxy (iso-propoxy) and propoxy. a

[0010] As used herein, the term "C1-C6 alkoxy C1-C6 alkyl" refers to a group of the formula R b where R is generally a C1-C6 alkyl group as defined above and R a is generally a C1-C6 alkylene group as defined above, of the formula R b OR a ​This refers to the group marked with -. "C1~C6 alkoxy C1~C6 alkyl", "C1~C4 alkoxy C1~C4 alkyl", "C1~C4 alkoxy C1~C3 alkyl", "C1~C4 alkoxy C1~C2 alkyl", and "C3~C4 alkoxy C1~C2 alkyl" should be interpreted accordingly. Examples of C1~C6 alkoxy C1~C6 alkyl, though not limited to these, include isopropoxymethyl, tert-butoxymethyl, 1-methoxyethyl, 1-isopropoxyethyl, and 1-tert-butoxyethyl.

[0011] As used herein, the term "C1-C6 alkoxycarbonyl" means R a However, the C1-C6 alkyl group is generally defined as above, formula R a This refers to the OC(O)- group. "C1-C4 alkoxycarbonyl" and "C1-C3 alkoxycarbonyl" should be interpreted accordingly.

[0012] As used herein, the term "C1-C6 alkoxycarbonyl C1-C4 alkyl" means R a However, these are generally C1-C6 alkyl groups as defined above, and R b However, the C1-C4 alkylene group, as defined above, is formula R a OC(O)R b - refers to the base of something.

[0013] As used herein, the term "C1-C6 alkoxy C1-C6 alkylcarbonyl" is R a However, these are generally C1-C6 alkyl groups as defined above, and R b However, the C1-C6 alkylene group, as defined above, is formula R a Ure b It refers to the C(O)- group.

[0014] As used herein, the term "C1-C6 alkylsulfanyl C1-C6 alkyl" means R aHowever, these are generally C1-C6 alkyl groups as defined above, and R b However, the C1-C6 alkylene group, as defined above, is formula R a SR b - refers to the base of something.

[0015] As used herein, the term "C1-C6 alkylsulfinyl C1-C6 alkyl" means R a However, these are generally C1-C6 alkyl groups as defined above, and R b However, the C1-C6 alkylene group, as defined above, is formula R a S(O)R b - refers to the base of something.

[0016] As used herein, the term "C1-C6 alkylsulfanyl C1-C6 alkylcarbonyl" is R a However, these are generally C1-C6 alkyl groups as defined above, and R b However, the C1-C6 alkylene group, as defined above, is formula R a SR b It refers to the C(O)- group.

[0017] As used herein, the term "C1-C6 alkylsulfinyl C1-C6 alkylcarbonyl" is R a However, these are generally C1-C6 alkyl groups as defined above, and R b However, the C1-C6 alkylene group, as defined above, is formula R a S(O)R b It refers to the C(O)- group.

[0018] As used herein, the term "C1-C6 alkylsulfonyl C1-C6 alkylcarbonyl" is R a However, these are generally C1-C6 alkyl groups as defined above, and R b However, the C1-C6 alkylene group, as defined above, is formula R a S(O)2R b It refers to the C(O)- group.

[0019] As used herein, the term "heterocyclyl" refers to a stable four-membered, five-membered, or six-membered non-aromatic monocyclic ring containing one, two, or three heteroatoms, the heteroatoms being individually selected from nitrogen, oxygen, and sulfur. The heterocyclyl group may be bonded to the remainder of the molecule via carbon atoms or heteroatoms. Examples of heterocyclyls, but not limited to, include azilidinyl, azetidinyl, oxetanyl, thietanyl, tetrahydrofuryl, pyrrolidinyl, pyrazolidinyl, imidazolidinyl, piperidinyl, piperazinyl, morpholinyl, dioxolanil, dithiolanyl, and thiazolidinyl.

[0020] As used herein, the term "heterocyclylcarbonyl" is R a However, the heterocyclyl portion defined above is, formula R a It refers to the C(O)- group.

[0021] The possibility of one or more chiral carbon atoms in a compound of formula (I) means that the compound can take on optical isomers, i.e., enantiomers or diastereoisomers. Furthermore, astrop isomers can be generated by the restriction of rotation involving single bonds. Formula (I) is intended to encompass all of these possible isomers and mixtures thereof. The present invention encompasses all of these possible isomers and mixtures thereof relating to compounds of formula (I). Similarly, formula (I) is intended to encompass all possible tautomers. The present invention encompasses all possible tautomers relating to compounds of formula (I).

[0022] In each case, the compound of formula (I) according to the present invention is in a free form, an oxidized form as an N-oxide, or a salt form such as an agriculturally usable salt form.

[0023] N-oxides are oxidized forms of tertiary amines or nitrogen-containing aromatic heterocyclic compounds. These are described, for example, in the book “Heterocyclic N-oxides”, A. Albini and S. Pietra, CRC Press, Boca Raton (1991).

[0024] The following list shows substituents A and R for the compound of formula (I). 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 This provides definitions including preferred definitions for each substituent. For any one of these substituents, any of the definitions shown below may be combined with any of the definitions of any other substituents shown below or elsewhere in this specification.

[0025] A is either CH or N. In one set of embodiments, A is CH. In another set of embodiments, A is N.

[0026] R 1 These are C1-C4 alkoxy C1-C2 alkyl, C1-C6 alkylsulfanyl C1-C6 alkyl, C1-C6 alkylsulfinyl C1-C6 alkyl, C1-C6 alkylsulfonyl C1-C6 alkyl, or heterocyclyl, where the heterocyclyl portion is a 4-membered, 5-membered, or 6-membered non-aromatic monocyclic ring containing 1, 2, or 3 heteroatoms individually selected from nitrogen, oxygen, and sulfur.

[0027] Preferably, R 1 These are C1-C4 alkoxy C1-C2 alkyl, C1-C3 alkylsulfanyl C1-C3 alkyl, C1-C3 alkylsulfinyl C1-C3 alkyl, C1-C3 alkylsulfonyl C1-C3 alkyl, or heterocyclyl, where the heterocyclyl portion is a 4-membered, 5-membered, or 6-membered non-aromatic monocyclic ring containing one or two heteroatoms individually selected from nitrogen and oxygen.

[0028] Comfortable, R 1 These are C1-C3 alkoxy C1-C2 alkyl, C1-C3 alkylsulfanyl C1-C3 alkyl, C1-C3 alkylsulfinyl C1-C3 alkyl, C1-C3 alkylsulfonyl C1-C3 alkyl, or heterocyclyl, where the heterocyclyl portion is a 4-membered, 5-membered, or 6-membered non-aromatic monocyclic ring containing a single oxygen atom.

[0029] Comfortable, R 1 These are C3-C4 alkoxy C1-C2 alkyl, C1-C3 alkylsulfanyl C1-C3 alkyl, C1-C3 alkylsulfinyl C1-C3 alkyl, C1-C3 alkylsulfonyl C1-C3 alkyl, or heterocyclyl, where the heterocyclyl portion is a 4-membered, 5-membered, or 6-membered non-aromatic monocyclic ring containing one or two heteroatoms individually selected from nitrogen and oxygen.

[0030] Furthermore, R 1 These are isopropoxymethyl, tert-butoxymethyl, 1-methoxyethyl, 1-isopropoxyethyl, 1-tert-butoxyethyl, C1-C3 alkylsulfanyl, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, or heterocyclyl, where the heterocyclyl portion is a 4-membered, 5-membered, or 6-membered non-aromatic monocyclic ring containing one or two heteroatoms individually selected from nitrogen and oxygen.

[0031] In a further preferred embodiment, R 1 These are isopropoxymethyl, tert-butoxymethyl, 1-methoxyethyl, 1-isopropoxyethyl, 1-tert-butoxyethyl, 1-methylsulfonylethyl, oxetan-3-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, or tetrahydropyran-4-yl.

[0032] In one embodiment, R 1These are C1-C6 alkoxy C1-C6 alkyl, C1-C6 alkylsulfanyl C1-C6 alkyl, C1-C6 alkylsulfinyl C1-C6 alkyl, C1-C6 alkylsulfonyl C1-C6 alkyl, or heterocyclyl, where the heterocyclyl portion is a 4-membered, 5-membered, or 6-membered non-aromatic monocyclic ring containing 1, 2, or 3 heteroatoms individually selected from nitrogen, oxygen, and sulfur.

[0033] Preferably, R 1 The C1-C4 alkoxy C1-C4 alkyl, C1-C4 alkylsulfanyl C1-C4 alkyl, C1-C4 alkylsulfinyl C1-C4 alkyl, C1-C4 alkylsulfonyl C1-C4 alkyl, or heterocyclyl, wherein the heterocyclyl portion is a 4-membered, 5-membered, or 6-membered non-aromatic monocyclic ring containing one or two heteroatoms individually selected from nitrogen, oxygen, and sulfur.

[0034] Comfortable, R 1 These are C1-C4 alkoxy C1-C3 alkyl, C1-C3 alkylsulfanyl C1-C3 alkyl, C1-C3 alkylsulfinyl C1-C3 alkyl, C1-C3 alkylsulfonyl C1-C3 alkyl, or heterocyclyl, where the heterocyclyl portion is a 4-membered or 5-membered non-aromatic monocyclic ring containing one or two heteroatoms individually selected from nitrogen and oxygen.

[0035] Furthermore, R 1 These are C1-C3 alkoxy C1-C3 alkyl, C1-C3 alkylsulfanyl C1-C3 alkyl, C1-C3 alkylsulfinyl C1-C3 alkyl, C1-C3 alkylsulfonyl C1-C3 alkyl, or heterocyclyl, where the heterocyclyl portion is a 4-membered or 5-membered non-aromatic monocyclic ring containing a single oxygen atom.

[0036] Furthermore, R 1These are isopropoxymethyl, tert-butoxymethyl, 1-methoxyethyl, 1-isopropoxyethyl, 1-tert-butoxyethyl, 1-methylsulfanylethyl, 1-methylsulfinylethyl, 1-methylsulfonylethyl, oxetan-3-yl, tetrahydrofuran-2-yl, or tetrahydrofuran-3-yl.

[0037] Most preferably, R 1 These are isopropoxymethyl, tert-butoxymethyl, 1-methoxyethyl, 1-isopropoxyethyl, 1-methylsulfonylethyl, oxetan-3-yl, tetrahydrofuran-2-yl, or tetrahydrofuran-3-yl.

[0038] In one embodiment, R 1 These are C1-C6 alkylsulfanyl, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, or heterocyclyl, where the heterocyclyl portion is a 4-membered, 5-membered, or 6-membered non-aromatic monocyclic ring containing 1, 2, or 3 heteroatoms individually selected from nitrogen, oxygen, and sulfur.

[0039] In another embodiment, R 1 The C1-C4 alkylsulfanyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, or heterocyclyl, where the heterocyclyl portion is a 4-membered, 5-membered, or 6-membered non-aromatic monocyclic ring containing one or two heteroatoms individually selected from nitrogen, oxygen, and sulfur.

[0040] In a further embodiment, R 1 These are C1-C3 alkylsulfanyl, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, or heterocyclyl, where the heterocyclyl portion is a 4-membered, 5-membered, or 6-membered non-aromatic monocyclic ring containing one or two heteroatoms individually selected from nitrogen and oxygen.

[0041] In a further embodiment, R 1 These are C1-C3 alkylsulfanyl, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, or heterocyclyl, where the heterocyclyl portion is a four-membered or five-membered non-aromatic monocyclic ring containing one or two heteroatoms individually selected from nitrogen and oxygen.

[0042] Furthermore, in other embodiments, R 1 These are C1-C3 alkylsulfanyl, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, or heterocyclyl, where the heterocyclyl portion is a 4-membered or 5-membered non-aromatic monocyclic ring containing a single oxygen atom.

[0043] In a preferred set embodiment, R 1 These are 1-methylsulfonylethyl, oxetan-3-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, or tetrahydropyran-4-yl.

[0044] In a more preferred set embodiment, R 1 These are 1-methylsulfanylethyl, 1-methylsulfinylethyl, 1-methylsulfonylethyl, oxetan-3-yl, tetrahydrofuran-2-yl, or tetrahydrofuran-3-yl.

[0045] In the most preferred set of embodiments, R 1 These are 1-methylsulfonylethyl, oxetan-3-yl, tetrahydrofuran-2-yl, or tetrahydrofuran-3-yl.

[0046] In a further preferred embodiment, R 1These are C3-C4 alkoxy C1-C3 alkyl, C1-C3 alkylsulfanyl C1-C3 alkyl, C1-C3 alkylsulfinyl C1-C3 alkyl, C1-C3 alkylsulfonyl C1-C3 alkyl, or heterocyclyl, where the heterocyclyl portion is a 4-membered or 5-membered non-aromatic monocyclic ring containing one or two heteroatoms individually selected from nitrogen and oxygen.

[0047] Preferably, R 1 isopropoxymethyl, tert-butoxymethyl, 1-isopropoxyethyl, 1-tert-butoxyethyl, 1-methylsulfanylethyl, 1-methylsulfinylethyl, 1-methylsulfonylethyl, oxetan-3-yl, tetrahydrofuran-2-yl, or tetrahydrofuran-3-yl. More preferably, R 1 These are isopropoxymethyl, tert-butoxymethyl, 1-isopropoxyethyl, 1-methylsulfonylethyl, oxetan-3-yl, tetrahydrofuran-2-yl, or tetrahydrofuran-3-yl.

[0048] R 2 is hydrogen or halogen. Preferably, R 2 is hydrogen, chloro, bromo, or fluoro. More preferably, R 2 is hydrogen or fluoro. In one set of embodiments, R 2 is hydrogen. In a further set of embodiments, R 2 It is fluoro.

[0049] R 3 is a C1-C8 alkyl group. Preferably, R 3 is a C1-C6 alkyl group. More preferably, R 3 is a C1-C3 alkyl group. More preferably, R 3 is methyl, ethyl, or isopropyl. Most preferably, R 3 It is methyl.

[0050] R 4 , R 5 , R6 is, independently of each other, hydrogen or C1-C4 alkyl. Preferably, R 4 , R 5 , R 6 is, independently of each other, hydrogen or C1-C3 alkyl. More preferably, R 4 , R 5 , R 6 is, independently of each other, hydrogen or methyl.

[0051] In one set of embodiments, R 4 is hydrogen, and R 5 and R 6 are both methyl.

[0052] R 7 is hydrogen, C1-C4 alkyl, C1-C6 alkoxycarbonyl C1-C4 alkyl, C1-C6 alkoxycarbonyl or C1-C6 alkoxy. Preferably, R 7 is hydrogen, C1-C3 alkyl, C1-C4 alkoxycarbonyl C1-C3 alkyl, C1-C4 alkoxycarbonyl or C1-C4 alkoxy. More preferably, R 7 is hydrogen, C1-C3 alkyl, C1-C3 alkoxycarbonyl C1-C2 alkyl, C1-C3 alkoxycarbonyl or C1-C3 alkoxy. Even more preferably, R 7 is hydrogen, methyl, methoxycarbonylmethyl, methoxycarbonyl or methoxy. More preferably, R 7 is hydrogen or methyl, and most preferably, R 7 is hydrogen.

[0053] R 8The carbon atom is hydrogen, a C1-C6 alkoxy carbonyl, a C1-C6 alkyl sulfanyl, a C1-C6 alkyl carbonyl, a C1-C6 alkyl sulfinyl, a C1-C6 alkyl carbonyl, or a heterocyclyl carbonyl, where the heterocyclyl portion is a 4-membered, 5-membered, or 6-membered non-aromatic monocyclic ring containing one, two, or three heteroatoms individually selected from nitrogen, oxygen, and sulfur.

[0054] Preferably, R 8 The carbon atom is hydrogen, a C1-C4 alkoxy carbonyl, a C1-C4 alkyl sulfanyl, a C1-C4 alkyl carbonyl, a C1-C4 alkyl sulfinyl, a C1-C4 alkyl carbonyl, or a heterocyclyl carbonyl, where the heterocyclyl portion is a 4-membered, 5-membered, or 6-membered non-aromatic monocyclic ring containing one or two heteroatoms individually selected from nitrogen, oxygen, and sulfur.

[0055] Comfortable, R 8 The carbon atom is hydrogen, a C1-C3 alkoxy C1-C3 alkylcarbonyl, a C1-C3 alkylsulfanyl C1-C3 alkylcarbonyl, a C1-C3 alkylsulfinyl C1-C3 alkylcarbonyl, a C1-C3 alkylsulfonyl C1-C3 alkylcarbonyl, or a heterocyclylcarbonyl, where the heterocyclyl portion is a four-membered or five-membered non-aromatic monocyclic ring containing one or two heteroatoms individually selected from nitrogen and oxygen.

[0056] Furthermore, R 8 The carbon atom is either hydrogen or a heterocyclylcarbonyl, and the heterocyclyl portion is a four- or five-membered non-aromatic monocyclic ring containing a single oxygen atom.

[0057] Furthermore, R 8 is hydrogen or tetrahydrofuran-3-carbonyl. Most preferably, R 8 It is hydrogen.

[0058] In the compound of formula (I) according to the present invention, preferably, A is either CH or N; R 1 These are C3-C4 alkoxy C1-C3 alkyl, C1-C3 alkylsulfanyl C1-C3 alkyl, C1-C3 alkylsulfinyl C1-C3 alkyl, C1-C3 alkylsulfonyl C1-C3 alkyl, or heterocyclyl, where the heterocyclyl portion is a 4-membered or 5-membered non-aromatic monocyclic ring containing a single oxygen atom; R 2 is hydrogen or fluorine; R 3 It is methyl; R 4 , R 5 and R 6 These are, independently, hydrogen or methyl; R 7 is hydrogen; and R 8 The carbon atom is either hydrogen or a heterocyclylcarbonyl, and the heterocyclyl portion is a four- or five-membered non-aromatic monocyclic ring containing a single oxygen atom.

[0059] Furthermore, A is N; R 1 These are C3-C4 alkoxy C1-C3 alkyl, C1-C3 alkylsulfanyl C1-C3 alkyl, C1-C3 alkylsulfinyl C1-C3 alkyl, C1-C3 alkylsulfonyl C1-C3 alkyl, or heterocyclyl, where the heterocyclyl portion is a 4-membered or 5-membered non-aromatic monocyclic ring containing a single oxygen atom; R 2 is hydrogen or fluorine; R 3 It is methyl; R 4 , R 5 and R 6 These are, independently, hydrogen or methyl; R 7 is hydrogen; and R 8 It is hydrogen or tetrahydrofuranyl.

[0060] More specifically, A is N; R 1 These are C1-C3 alkylsulfanyl, C1-C3 alkylsulfinyl, C1-C3 alkyl, C1-C3 alkylsulfonyl, or heterocyclyl, where the heterocyclyl portion is a 4-membered or 5-membered non-aromatic monocyclic ring containing a single oxygen atom; R 2 is hydrogen or fluorine; R 3 It is methyl; R 4 is hydrogen; R 5 and R 6 Both are methyl; R 7 is hydrogen; and R 8 It is hydrogen.

[0061] In a further preferred embodiment, in the compound of formula (I) according to the present invention, preferably A is N; R 1 These are C1-C4 alkoxy C1-C2 alkyl, C1-C6 alkylsulfanyl C1-C6 alkyl, C1-C6 alkylsulfinyl C1-C6 alkyl, C1-C6 alkylsulfonyl C1-C6 alkyl, or heterocyclyl, where the heterocyclyl portion is a 4-membered, 5-membered, or 6-membered non-aromatic monocyclic ring containing 1, 2, or 3 heteroatoms individually selected from nitrogen, oxygen, and sulfur; R 2 is hydrogen or fluorine; R 3 It is methyl; R 4 is hydrogen; R 5 and R 6 Both are methyl; R 7 is hydrogen; and R 8 It is hydrogen.

[0062] More preferably, A is N; R 1 is isopropoxymethyl, tert-butoxymethyl, 1-methoxyethyl, 1-isopropoxyethyl, 1-tert-butoxyethyl, C1-C3 alkylsulfanyl C1-C3 alkyl, C1-C3 alkylsulfinyl C1-C3 alkyl, C1-C3 alkylsulfonyl C1-C3 alkyl or heterocyclyl, and the heterocyclyl moiety is a 4-, 5- or 6-membered non-aromatic monocyclic ring containing 1 or 2 heteroatoms individually selected from nitrogen and oxygen; R 2 is hydrogen or fluoro; R 3 is methyl; R 4 is hydrogen; R 5 and R 6 are both methyl; R 7 is hydrogen; and R 8 is hydrogen.

[0063] Preferably, the compound of formula (I) is 2-[(2,6-difluoro-4-pyridyl)-(tetrahydrofuran-3-carbonyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-N-(tetrahydrofuran-3-carbonyl)thiazole-4-carboxamide (P-1); 2-[(2,6-difluoro-4-pyridyl)-(tetrahydrofuran-2-carbonyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (P-2); 2-[(2,6-difluoro-... 2-[(2,6-difluoro-4-pyridyl)-(oxetane-3-carbonyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (P-4); 2-[2-tert-butoxypropanoyl-(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide(P-5); 2-[(2,6-difluoro-4-pyridyl)-(2-isopropoxypropanoyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide(P-6); 2-[(2-tert-butoxyacetyl)-(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide(P-7); 2-[(2,6-difluoro-4-pyridyl)-(2-isopropoxyacetyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide(P-8); 2-[(2,6-difluoro-4-pyridyl)-(2-methoxypropanoyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide(P-9); 2-[(2,6-difluoro-4-pyridyl)-(2-methylsulfonylpropanoyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (P-10); and 2-[(2,6-difluoro-4-pyridyl)-(tetrahydropyran-4-carbonyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (P-11) Selected from.

[0064] The compounds of the present invention can be formed as shown in the following scheme, and here, unless otherwise specified, the definition of each variable element is as defined above for the compound of formula (I).

[0065] The compound of formula (Ia) according to the present invention (where R 1 , R 2 , R 3 , R 4 , R5 , R 6 and R 7 This is defined for equation (I), and R 8 (where R is hydrogen) is a compound of formula (III) (where R is hydrogen), which is heated or aided by a base. 1 The compound of formula (II) (where A, R is defined for formula (I), and Xa is a halogen, preferably bromo or chloro) is defined as follows: and Xa is a halogen, preferably bromo or chloro) 2 , R 3 , R 4 , R 5 , R 6 and R 7 This can be obtained by the transformation (as defined for equation (I)). This is shown in scheme 1 (below). Scheme 1 [ka]

[0066] Those skilled in the art will recognize that the conditions used to prepare the compound of formula (Ia) will depend on the stoichiometry of the reaction. For example, reacting 1 to 1.5 equivalents of the compound of formula (III) with 1 equivalent of the compound of formula (II) will mainly produce the compound of formula (Ia), while reacting 2 to 2.1 equivalents of the compound of formula (III) with 1 equivalent of the compound of formula (II) will produce the compound of formula (Ib) (where R 8a These are C1-C6 alkoxy C1-C6 alkylcarbonyl, C1-C6 alkylsulfanyl C1-C6 alkylcarbonyl, C1-C6 alkylsulfinyl C1-C6 alkylcarbonyl, C1-C6 alkylsulfonyl C1-C6 alkylcarbonyl, or heterocyclylcarbonyl, where heterocyclyl is a 4-membered, 5-membered, or 6-membered non-aromatic monocyclic ring containing 1, 2, or 3 heteroatoms individually selected from nitrogen, oxygen, and sulfur. This is shown in Scheme 2 (below). Scheme 2 [ka]

[0067] Compound of formula (II) (where A, R 2 , R 3 , R 4 , R 5 , R 6 and R 7 The compound of formula (V) (where R is defined in formula (I)) is a compound of formula (V) (where R is a compound of formula (V)) obtained by heating, base assistance, or transition metal catalysis Buchwald-Hartwig amination. 3 , R 4 , R 5 , R 6 and R 7 A and R are as defined in formula (I), and Xb is a halogen, preferably bromo or chloro) and a compound of formula (IV) (where A and R are as defined in formula (I), and Xb is a halogen, preferably bromo or chloro) 2 This can be obtained by the transformation of (as defined in formula (I)). This is shown in scheme 3 (below). Such compounds of formula (II) are described in International Publication No. 2019 / 105933. Scheme 3 [ka]

[0068] Compound of formula (V) (where R 3 , R 4 , R 5 , R 6 and R 7 (where R is as defined in formula (I), and Xb is a halogen, preferably bromo or chloro) is used to form a compound of formula (VI) (where R is as defined in formula (I), and Xb is a halogen, preferably bromo or chloro) via an intermediate acid chloride or directly with a peptide coupling agent. 2 R is as defined in formula (I), and Xb is a halogen, preferably a bromo) and a compound of formula (VII) (where 4 , R 5 , R 6 and R 7 This can be obtained by the transformation (as defined in equation (I)). This is shown in scheme 4 (below). Scheme 4 [ka]

[0069] Compound of formula (VI) (where R 3 (where R is defined as in formula (I) and Xb is a halogen, preferably bromo or chloro) is a compound of formula (VIII) (where R 3 The formula (I) is defined as follows, where Xb is a halogen, preferably bromo or chloro, and R 9 This can be obtained by the conversion of a C1-C6 alkyl group and a base. This is shown in Scheme 5 (below). Scheme 5 [ka]

[0070] Instead, the compound of formula (II) (where R 2 And A is as defined for formula (I)) and the compound of formula (VII) (where R is defined as 4 , R 5 , R 6 and R 7 The compound of formula (IX) by formula (I) (where R is defined as R 2 , R 3 And A can be obtained by the transformation (as defined for equation (I)). This is shown in scheme 6 (below). Scheme 6 [ka]

[0071] Compound of formula (IX) (where R 2 , A and R 3As defined for formula (I), a compound of formula (X) (where R is R) is formed with a base. 2 , R 3 And A is as defined for equation (I), and R 10 This can be obtained by the conversion of a C1-C6 alkyl group. This is shown in Scheme 7 (below). Scheme 7 [ka]

[0072] Compound of formula (X) (where R 2 , A and R 3 This is defined in equation (I), and R 10 The compound of formula (VII) (where R is a C1-C6 alkyl group) is subjected to heating, base-assisted or transition metal-catalyzed Buchwald-Hartwig amination. 3 The following is defined in formula (I), where Xb is a halogen, preferably bromo or chloro, and R 10 Compounds of formula (IV) by (where A and R are C1-C6 alkyl groups) 2 This can be obtained by the transformation (as defined in equation (I)). This is shown in scheme 8 (below). Scheme 8 [ka]

[0073] Instead, the compound of formula (X) (where R 2 , A and R 3 This is defined for equation (I), and R 10 The compound of formula (XII) (where R is a C1-C6 alkyl group) under transition metal catalysis Buchwald-Hartwig amination conditions. 3 This is defined for equation (I), and R 10A compound of formula (XI) (where R is a C1-C6 alkyl group) 2 And A are as defined in formula (I), and Xc can be obtained by conversion of a halogen, preferably bromo or iodine. This is shown in scheme 9 (below). Scheme 9 [ka]

[0074] Instead, the compound of formula (II) (where A, R) 2 , R 3 , R 4 , R 5 , R 6 and R 7 (As defined for formula (I)) is a compound of formula (XIII) (where R is used in the following manner): heating, base-assisted or transition metal-catalyzed Buchwald-Hartwig amination. 3 , R 4 , R 5 , R 6 and R 7 Compounds of formula (XI) by formula (I) (where A and R are defined as follows): 2 This is as defined for formula (I), and can be obtained by the conversion of a halogen (where Xc is preferably bromo or iodine). This is shown in scheme 10 (below). Scheme 10 [ka]

[0075] Surprisingly, it was found that the novel compound of formula (I) possesses a very advantageous level of biological activity for practical purposes, protecting plants from fungal diseases.

[0076] The compound of formula (I) can be used in the agricultural sector and related fields of use as an active ingredient for controlling plant pests or non-biological materials, and for controlling putrefactive microorganisms or organisms that are potentially harmful to humans. The novel compound is outstanding for its excellent activity at low application rates, excellent tolerance by plants, and environmental safety. It has extremely useful therapeutic, preventive, and systemic properties and can be used to protect many cultivated plants. The compound of formula (I) can be used to inhibit or eliminate pests that occur on plants or parts of plants (fruits, flowers, leaves, stems, tubers, roots) of different crops of useful plants, while simultaneously protecting these parts of the plant from, for example, plant pathogenic microorganisms as they grow.

[0077] The present invention further relates to a method for controlling or preventing ectoparasites of plants or plant reproductive bodies and / or harvested edible crops that are susceptible to microbial damage by treating the plants or plant reproductive bodies and / or harvested edible crops, wherein an effective amount of the compound of formula (I) is applied to the plants, a part thereof, or their habitat.

[0078] Compounds of formula (I) can also be used as fungicides and fungicides. The term "fungicide and fungicide," as used herein, means a compound that controls, denatures, or prevents the growth of fungi. The term "fungicide-effective amount" means an amount of such compound or combination of such compounds that is capable of producing an effect on the growth of fungi. Controlling or denature effects include all deviations from natural development, such as death or delay, while prevention includes the formation of barriers or other defenses in plants to prevent fungal infection.

[0079] For protection against fungal infections occurring in the soil and against plant pathogenic fungi, the compound of formula (I) can also be used as a coating agent for plant reproductive bodies such as seeds (e.g., fruits, tubers, or grains) or plant cuttings (e.g., rice). These reproductive bodies can be treated with a composition containing the compound of formula (I) before planting. For example, seeds can be coated before sowing.

[0080] The active ingredients of the present invention can also be applied to grains by impregnating them in a liquid formulation or by coating the seeds with a solid formulation. The composition can also be applied to the planting site when the planting stock is planted, for example, by applying it to the sowing furrow during sowing. The present invention also relates to a method for treating such plant stocks and to plant stocks treated in this manner.

[0081] Furthermore, the compounds according to the present invention can be used, for example, to control fungi in related fields such as the protection of industrial materials including wood and wood-based industrial products, food storage, and hygiene management.

[0082] In addition, the present invention can be used, for example, to protect non-biological materials such as timber, wall panels, and paints from fungal action.

[0083] Compounds of formula (I) may be effective against, for example, fungi and fungal vectors related to diseases, as well as plant pathogenic bacteria and viruses. These fungi and fungal vectors related to diseases, as well as plant pathogenic bacteria and viruses, are, for example, as follows: The fungi and fungal vectors, as well as plant pathogenic bacteria and viruses, that can be controlled for these diseases include, for example, the following: Absidia corymbifera, Alternaria spp., Aphanomyces spp., Ascochyta spp., Aspergillus spp. including A. flavus, A. fumigatus, A. nidulans, A. niger, A. terrus, Aureobasidium spp. including A. pullulans, Blastomyces dermatitidis, Blumeria graminis, Bremia lactucaea This includes species of the genus Botryosphaeria (B. lactucae), B. dothidea, B. obtusa, species of the genus Botrytis (including B. cinerea), species of Candida (C. albicans, C. glabrata, C. krusei, C. lusitaniae, C. parapsilosis, C. tropicalis), species of Cephaloascus fragrans, and species of Ceratocystis. Cercospora spp. (including C. arachidicola), Cercosporidium personatum, Cladosporium spp., Claviceps purpurea, Coccidioides immitis, a species of the genus Cochliobolus, and a species of the genus Colletotrichum, including C. musae. Cryptococcus neoformans, species of the genus Diaporthe, species of the genus Didymella, species of the genus Drechslera, species of the genus Elsinoe, Species of the genus Epidermophyton (Epidermophyton spp.), including Erwinia amylovora and Erysiphe species (E. cichoracearum), Fusarium spp., including species such as Eutypa lata, F. culmorum, F. graminearum, F. langsethiae, F. moniliforme, F. oxysporum, F. proliferatum, F. subglutinans, and F. solani, as well as Gaeumannomyces graminis, Gibberella fujikuroi, Gloeodes pomigena, Gloeosporium musarum, and Glomerella singlet. cingulate), Guignardia bidwellii, Gymnosporangium juniperi-virginianae, species of Helminthosporium, species of Hemileia, species of Histoplasma including H. capsulatum, Laetisaria fuciformis, Leptographium lindbergi, Leveillula taurica, Lophodermium seditiosum, wheat mold (Microdochium nivale), species of Microsporum This includes species of the genus Monilinia (spp.), species of the genus Mucor (spp.), wheat leaf spot fungus (M. graminicola), and species of the genus Mycosphaerella (spp.), including M. pomi.), Oncobasidium theobromaeon, Ophiostoma piceae, species of the genus Paracoccidioides spp., species of the genus Penicillium including P. digitatum and P. italicum, species of the genus Petriellidium spp., species of the genus Peronosclerospora including P. maydis, P. philippinensis and P. sorghi, species of the genus Peronospora spp., species of Peronospora spp., wheat blight fungus (Phaeosphaeria) (P. nodorum), Phakopsora pachyrhizi, Phellinus igniarus, a species of the genus Phialophora, a species of the genus Phoma, a species of Phoma, a species of genus Phomopsis viticola, a species of genus Phytophthora including P. infestans, a species of genus Plasmopara including P. halstedii, P. viticola, a species of genus Pleospora, a species of genus Podosphaera including apple powdery mildew (P. leucotricha), Polymyxa graminis Pseudoperonospora spp. includes species such as P. graminis, Polymyxa betae, Pseudocercosporella herpotrichoides, species of Pseudomonas, P. cubensis, and P. humuli.), species of the genus Puccinia (including Pseudopeziza tracheiphila, P. hordei, P. recondita, P. striiformis, P. triticina), species of the genus Pyrenopeziza, species of the genus Pyrenophora, species of the genus Pyrenophora, species of the genus Pyricularia (including P. oryzae), species of the genus Pythium (including P. ultimum), species of the genus Ramularia, species of the genus Rhizoctonia, and Rhizomucor This includes species such as *Rhizopus pusillus*, *Rhizopus arrhizus*, species of the genus *Rhynchosporium* (including *S. apiospermum* and *S. prolificans*), species of the genus *Scedosporium* (including *S. apiospermum* and *S. prolificans*), and *Schizothyrium pomi*. Species of the genera Sclerotinia, Sclerotium, Septoria (including S. nodorum and S. tritici), Sphaerotheca macularis, Sphaerotheca fusca (Sphaerotheca fuliginea), Sporothorix, Stagonospora nodorum, Stemphylium, Stereum hirsutum, Thanatephorus cucumeris, and Thielaviopsis basicola. Tilletia spp. (including T. basicola), T. harzianum, T. pseudokoningii, and T. viride, Species of the genera Trichophyton, Typhula, Uncinula necator, Urocystis, Ustilago, Venturia (including V. inaequalis), Verticillium, and Xanthomonas.

[0084] Within the scope of the present invention, target crops and / or useful plants to be protected are typically berries such as blackberries, blueberries, cranberries, raspberries, and strawberries; cereals such as barley, corn, millet, oats, rice, rye, sorghum, and wheat; fiber plants such as cotton, flax, hemp, jute, and sisal; crops such as sugars and fodder beets, coffee, hops, mustard, rapeseed (canola), poppies, sugarcane, sunflowers, tea, and tobacco; fruit trees such as apples, apricots, avocados, bananas, cherries, citrus fruits, nectarines, peaches, pears, and plums; and grasses such as Bermuda grass, strawberry grass, bentgrass, centipede grass, bog grass, ryegrass, American grass, and Zoysia grass. Herbs such as basil, borage, chives, coriander, lavender, lavage, mint, oregano, parsley, rosemary, sage, and thyme; legumes such as kidney beans, lentils, peas, and soybeans; nuts such as almonds, cashews, peanuts, hazelnuts, pecans, pistachios, and walnuts; palms such as oil palm; ornamental plants such as flowers, shrubs, and trees; other trees such as cocoa, coconut, olive, and rubber; vegetables such as asparagus, eggplant, broccoli, cabbage, carrots, cucumbers, garlic, lettuce, pumpkin, melon, okra, onions, pepper, potatoes, pumpkins, rhubarb, spinach, and tomatoes; and perennial and annual crops such as climbing plants such as grapes.

[0085] The term "useful plants" should be understood to include useful plants in which resistance to herbicides such as bromoxynil or certain classifications of herbicides (e.g., HPPD inhibitors, ALS inhibitors such as primisulfuron, prosulfuron, and trifloxysulfuron, EPSPS (5-enol-pyrovir-shikimate-3-phosphate-synthase) inhibitors, GS (glutamine synthetase) inhibitors, or PPO (protoporphyrinogen-oxidase) inhibitors) has been acquired through conventional crossbreeding or genetic engineering methods. An example of a crop in which resistance to imidazolinones such as imazamox has been acquired through conventional crossbreeding methods (mutaogenesis) is Clearfield® summer rapeseed (canola). Examples of crops in which resistance to herbicides or a certain class of herbicides has been induced through genetic engineering include glyphosate and glufosinate-resistant maize varieties marketed under trade names RoundupReady®, Herculex I®, and LibertyLink®.

[0086] The term "useful plants" should be understood to include useful plants that have been transformed using recombinant DNA technology to synthesize one or more selectively acting toxins, such as those from known toxin-producing bacteria, particularly those of the genus Bacillus.

[0087] Examples of such plants include: YieldGard® (maize variety expressing Cry(IA)(b) toxin); YieldGard Root-Eater Nematode® (maize variety expressing CryIIIB(b1) toxin); YieldGard Plus® (maize variety expressing Cry(IA)(b) and CryIIIB(b1) toxins); Starlink® (maize variety expressing Cry9(c) toxin); Herculex I® (maize variety expressing CryIF(a2) toxin and the enzyme phosphinothrysin N-acetyltransferase (PAT) to achieve resistance to the herbicide glufosinate ammonium); NuCOTN 33B® (cotton variety expressing Cry(IA)(c) toxin); Bollgard I® (cotton variety expressing Cry(IA)(c) toxin); Bollgard II(registered trademark) (cotton varieties expressing Cry(IA)(c) and CryI(IA)(b) toxins); VIPCOT(registered trademark) (cotton varieties expressing VIP toxin); NewLeaf(registered trademark) (potato varieties expressing CryII(IA) toxin); NatureGard(registered trademark), Agrisure(registered trademark) GT advantages (GA21 glyphosate resistance trait), Agrisure(registered trademark) CB advantages (Bt11 corn-boring insect (CB) trait), Agrisure(registered trademark) RW (corn root-boring nematode trait), and Protecta(registered trademark).

[0088] The term "crop" should be understood to include crop plants transformed using recombinant DNA technology to enable the synthesis of one or more selectively acting toxins, such as those from known toxin-producing bacteria, particularly those of the genus Bacillus.

[0089] Toxins that may be expressed by transgenic plants include, for example, insecticidal proteins derived from Bacillus cereus or Bacillus popilliae; or insecticidal proteins derived from Bacillus thuringiensis, such as δ-endotoxins like Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C; or vegetative insecticidal proteins (Vip) such as Vip1, Vip2, Vip3 or Vip3A; or species of the genus Photorhabdus, such as Photorhabdus luminescens or Xenorhabdus nematophilus, such as species of the genus Photorhabdus or Xenorhabdus Insecticidal proteins of nematode-symbiotic bacteria such as spp.; toxins produced by animals such as scorpion toxin, spider toxin, large wasp (wasp) toxin and other insect-specific neurotoxins; toxins produced by fungi such as Streptomycete toxin, plant lectins such as pea lectin, barley lectin or snowdrop lectin; aglutinin; proteinase inhibitors such as trypsin inhibitors, serine protease inhibitors, patain, cystatin, papain inhibitors; lysine, Examples include ribosome-inactivating proteins (RIPs) such as maize-RIP, abrin, rufin, saporin, or briodin; steroid metabolic enzymes such as 3-hydroxysteroid xidase, ecdysteroid-UDP-glycosyl-transferase, cholesterol oxidase, ecdysone inhibitors, and HMG-COA-reductase; ion channel blockers such as sodium or calcium blockers; larval hormone esterases; diuretic hormone receptors; stilbene synthase, bibenzyl synthase, chitinase, and glucanase.

[0090] In connection with the present invention, it should be understood that δ-endotoxins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, or Cry9C, or vegetative insecticidal proteins (Vip) such as Vip1, Vip2, Vip3, or Vip3A, are also hybrid toxins, cleavage toxins, and modified toxins. Hybrid toxins are generated by recombinant synthesis through novel combinations of different domains of these proteins (see, for example, International Publication No. 02 / 15701). For example, cleavage toxins such as cleavage Cry1Ab are known. In the case of modified toxins, one or more amino acids of the natural toxin are substituted. In such amino acid substitutions, preferably, a protease recognition sequence that does not naturally exist is inserted into the toxin. For example, in the case of Cry3A055, a cathepsin-G recognition sequence is inserted into the Cry3A toxin (see International Publication No. 03 / 018810).

[0091] Examples of such toxins or transgenic plants capable of synthesizing such toxins are disclosed, for example, in European Patent Publication No. 0374753, International Publication No. 93 / 07278, International Publication No. 95 / 34656, European Patent Publication No. 0427529, European Patent Publication No. 451878, and International Publication No. 03 / 052073.

[0092] The process for preparing such transformed plants is generally known to those skilled in the art and is described, for example, in the publications mentioned above. CryI-type deoxyribonucleic acid and its preparation are known, for example, from International Publication No. 95 / 34656, European Patent Application Publication No. 0367474, European Patent Application Publication No. 0401979, and International Publication No. 90 / 13651.

[0093] The toxins contained in transgenic plants confer resistance to harmful insects. Such insects can belong to any of the insect taxonomic groups, but are commonly found in beetles (Coleoptera), diptera (Diptera), and butterflies (Lepidoptera).

[0094] Transgenic plants containing one or more genes encoding insecticide resistance and expressing one or more toxins are known, and some of them are commercially available. Examples of such plants include: YieldGard® (maize variety expressing Cry1Ab toxin); YieldGard Rootworm® (maize variety expressing Cry3Bb1 toxin); YieldGard Plus® (maize variety expressing Cry1Ab and Cry3Bb1 toxins); Starlink® (maize variety expressing Cry9C toxin); Herculex I® (maize variety expressing Cry1Fa2 toxin and the enzyme phosphinothricin N-acetyltransferase (PAT) to achieve resistance to the herbicide glufosinate ammonium); NuCOTN 33B® (cotton variety expressing Cry1Ac toxin); Bollgard I® (cotton variety expressing Cry1Ac toxin); Bollgard These include II (registered trademark) (cotton varieties expressing Cry1Ac and Cry2Ab toxins); VipCot (registered trademark) (cotton varieties expressing Vip3A and Cry1Ab toxins); NewLeaf (registered trademark) (potato varieties expressing Cry3A toxin); NatureGard (registered trademark), Agrisure (registered trademark) GT Advantage (GA21 glyphosate resistance trait), Agrisure (registered trademark) CB Advantage (Bt11 corn-boring insect (CB) trait), and Protecta (registered trademark).

[0095] Further examples of such transformed crops are as follows: 1. Bt11 maize, manufactured by Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31, 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10. Genetically modified maize (Zea mays) conferring resistance to the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) through transgenic expression of the cleavage-type Cry1Ab toxin. Bt11 maize also achieves resistance to the herbicide glufosinate ammonium through transgenic expression of the enzyme PAT.

[0096] 2. Bt176 maize, manufactured by Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10. Genetically modified maize (Zea mays) conferred resistance to the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) through transgenic expression of Cry1Ab toxin. Bt176 maize also achieves resistance to the herbicide glufosinate ammonium through transgenic expression of the enzyme PAT.

[0097] 3. Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31, 790 St. Sauveur, France, MIR604 maize, registration number C / FR / 96 / 05 / 10. Maize conferred insect resistance by transgenic expression of modified Cry3A toxin. This toxin is Cry3A055 modified by insertion of a cathepsin-G-protease recognition sequence. The preparation of such transgenic maize plants is described in International Publication No. 03 / 018810.

[0098] 4. Monsanto Europe SA270-272 Avenue de Tervuren, B-1150 Brussels, Belgium. MON863 maize, registration number C / DE / 02 / 9. MON863 expresses the Cry3Bb1 toxin and is resistant to certain Coleopteran insects.

[0099] 5. Monsanto Europe, SA270-272 Avenue de Tervuren, B-1150 Brussels, Belgium. IPC531 cotton, registration number C / ES / 96 / 02.

[0100] 6. 1507 maize, manufactured by Pioneer Overseas Corporation, Avenue Tedesco, 7 B-1160 Brussels, Belgium, registration number C / NL / 00 / 10. Genetically engineered maize for the expression of the protein Cry1F to achieve resistance to specific lepidopteran insects and the PAT protein to achieve resistance to the herbicide glufosinate ammonium.

[0101] 7. Monsanto Europe SA270-272 Avenue de Tervuren, B-1150 Brussels, Belgium. NK603×MON810 maize, registration number C / GB / 02 / M3 / 03. This is a conventional hybrid maize variety created by crossing the genetically modified varieties NK603 and MON810. NK603×MON810 maize transgenically expresses the protein CP4 EPSPS obtained from strain CP4 of a species of Agrobacterium sp., thereby conferring resistance to the herbicide Roundup® (containing glyphosate). It also transgenicly expresses the Cry1Ab toxin obtained from Bacillus thuringiensis subsp. kurstaki, thereby providing resistance to certain lepidopteran moths, including the European corn borer.

[0102] Furthermore, the compounds of formula (I) (including any one of the compounds listed in Table 2 (below)) and the following species have been identified: Absidia corymbifera, Alternaria spp., Aphanomyces spp., Ascochyta spp., Aspergillus spp. including A. flavus, A. fumigatus, A. nidulans, A. niger, A. terrus, Aureobasidium spp. including A. pullulans, Blastomyces dermatitidis, and Blumeria graminis. This includes species of the genus Botryosphaeria (including Botryosphaeria graminis, Bremia lactucae, B. dothidea, and B. obtusa), species of the genus Botrytis (including B. cinerea), species of Candida (including C. albicans, C. glabrata, C. krusei, C. lusitaniae, C. parapsilosis, and C. tropicalis), species of Cephaloascus fragrans, and species of the genus Ceratocystis. Cercospora spp., including C. arachidicola.), Cercosporidium personatum, species of Cladosporium, Claviceps purpurea, Coccidioides immitis, species of Cochliobolus, species of Colletotrichum including C. musae, Cryptococcus neoformans, species of Diaporthe, species of Didymella, species of Drechslera, species of Elsinoe, species of Epidermophyton Fusarium spp. includes species such as Erwinia amylovora, E. cichoracearum, Erysiphe spp., Eutypa lata, F. culmorum, F. graminearum, F. langsethiae, F. moniliforme, F. oxysporum, F. proliferatum, F. subglutinans, and F. solani.), Gaeumannomyces graminis, Gibberella fujikuroi, Gloeodes pomigena, Gloeosporium musarum, Glomerella cingulate, Guignardia bidwellii, Gymnosporangium juniperi-virginianae, species of Helminthosporium, species of Hemileia, species of Histoplasma including H. capsulatum, Laetisaria fusiformis *Leptographium fuciformis*, *Leptographium lindbergi*, *Leveillula taurica*, *Lophodermium seditiosum*, *Microdochium nivale*, species of *Microsporum*, species of *Monilinia*, species of *Mucor*, *M. graminicola*, species of *Mycosphaerella* including *M. pomi*, *Oncobasidium theobromaeon*, *Ophiostoma piceae*, species of *Paracoccidioides* Penicillium spp., including P. digitatum and P. italicum, Petriellidium spp., P. maydis, P. philippinensis and P. sorghi (P.Species of the genus Peronosclerospora (including sorghi), species of Peronospora (spp.), wheat blight fungus (Phaeosphaeria nodorum), Phakopsora pachyrhizi, Phellinus igniarus, species of the genus Phialophora (spp.), species of the genus Phoma (spp.), species of the genus Phytophthora (spp. including Phomopsis viticola, P. infestans), species of the genus Plasmopara (including P. halstedii, P. viticola) Pleospora spp., Podosphaera spp. including apple powdery mildew fungus (P. leucotricha), Polymyxa graminis, Polymyxa betae, Pseudocercosporella herpotrichoides, Pseudomonas spp., Pseudoperonospora spp. including P. cubensis and P. humuli, Pseudopeziza Puccinia spp., which includes species of the genus Puccinia (P. tracheiphila), P. hordei, P. recondita, P. striiformis, P. triticina; Pyrenopeziza spp.; Pyrenophora spp., which includes species of the genus Pyrenophora; Pyricularia spp., which includes the rice blast fungus (P. oryzae); and Pythium spp., which includes species of the genus Pythium (P. ultimum).), species of the genus Ramularia, species of Rhizoctonia, Rhizomucor pusillus, Rhizopus arrhizus, species of Rhynchosporium, species of Sedosporium including S. apiospermum and S. prolificans, species of Schizothyrium pomi, species of Sclerotinia, species of Sclerotium, species of Septoria including S. nodorum and S. tritici Sphaerotheca macularis, Sphaerotheca fusca (Sphaerotheca fuliginea), a species of Sporothorix (spp.), Stagonospora nodorum, a species of Stemphylium (spp.), Stereum hirsutum, Thanatephorus cucumeris, Thielaviopsis basicola, a species of Tilletia Trichoderma spp. (including T. harzianum, T. pseudokoningii, T. viride), Trichophyton spp., Typhula spp., Uncinula necator, Urocystis spp., Ustilago spp., Venturia spp. (including V. inaequalis)), species of the genus Verticillium and species of the genus Xanthomonas, in particular wheat leaf spot fungus (Zymoseptoria tritici), wheat red rust fungus (Puccinia recondita), wheat yellow rust fungus (Puccinia striiformis), barley powdery mildew fungus (Erysiphe graminis), grape powdery mildew fungus (Uncinula necator), cucumber powdery mildew fungus (Sphaerotheca fuliginea), tomato powdery mildew fungus (Leveillula taurica), soybean rust fungus (Phakopsora pachyrhizi), rice blast fungus (Pyricularia oryzae), tomato ring spot fungus (Alternaria solani), Alternaria alternata (Alternaria (alternata), Mycosphaerella fijiensis, Cucurbit anthracnose fungus (Colletotrichum lagenarium), Cucurbit vine blight fungus (Didymella bryoniae), Pea brown spot fungus (Ascochyta pisii), Verticillium dahliae, Barley reticulate blight fungus (Pyrenophora teres), Sugar beet brown spot fungus (Cercospora. No cross-resistance has been observed with any fungicidal or mycogenic solution used to control plant pathogenic fungi and molds such as beticola, Ramularia collo-cygni, Botrytis cinerea, Sclerotinia sclerotiorum, Monilinia laxa, Monographaella nivalis, and Venturia inaequalis.

[0103] In fact, fungicide-resistant strains in any of the species outlined above have been reported in the scientific literature, along with strains resistant to one or more fungicides from at least one of the following fungicide-resistant mechanism classes: quinone external inhibitors (QoIs), quinone internal inhibitors (QiIs), succinate dehydrogenase inhibitors (SDHIs), and sterol demethylation inhibitors (DMIs). Such fungicide-resistant strains may include: • Mutations in the mitochondrial cytochrome b gene that confer resistance to Qo inhibitors, where the mutations are G143A, F129L, or G137R. See, for example, Gisi et al., Pest Manag Sci 56, 833-841, (2000), Lucas, Pestic Outlook 14(6), 268-70 (2003), Fraaije et al., Phytopathol 95(8), 933-41 (2005), Sierotzki et al., Pest Manag Sci 63(3), 225-233 (2007), Semar et al., Journal of Plant Diseases and Protection (3), 117-119 (2007); and Pasche et al., Crop Protection 27(3-5), 427-435 (2008). • Mutations in the mitochondrial cytochrome b gene that confer resistance to Qi inhibitors, specifically the G37A / C / D / S / V mutation. See, for example, Meunier et al., Pest Manag Sci 2019;75:2107-2114. • Mutations in the genes encoding the SdhB, C, and D subunits that confer resistance to SDHI inhibitors, where the mutations are present in the following major pathogens: ○ Botrytis cinerea: B-P225H / L / T / Y / F, B-N230I, B-H272L / Y / R, C-P80H / L, C-N87S; ○Tomato ring spot disease fungus (Alternaria solani): B-H278R / Y, C-H134R / Q, D-D123E, D-H133R and C-H134R; ○ Wheat leaf blight fungus (Zymoseptoria tritici): sdhB: N225T, N225I, R265P, T268I, T268A. In sdhC: T79N, T79I, W80S, W80A, A84F, N86S, N86A, P127A, R151M / S / T / G, R151S, R151T, H152R / Y, V166M, T168R. In sdhD: I50F, M114V, D129G, T20P+K186R; ○ Barley net spot disease fungus (Pyrenophora teres): In sdhB: S66P, N235I, H277Y. In sdhC: K49E, R64K, N75S, G79R, H134R, S135R. In sdhD: D124E, H134R, G138V, D145G; ○Ramularia collo-cygni: In sdhB: N224T, T267I. In sdhC: N87S, G91R, H146R / L, G171D, H153R; ○Soybean rust fungus (Phakopsora pachyrhizi): C-I86F; ○ Endive sclerotinia pathogen (Sclerotinia sclerotiorum): In sdhB: H273Y. In sdhC: G91R, H146R. In sdhD: T108K, H132R, G150R.

[0104] The main sources are www.frac.info, Sierotzki and Scalliet Phytopathology (2013) 103(9):880-887 and Simoes et al., J Plant Dis Prot (2018) 125:21-2. • Mutations or combinations of mutations in the CYP51 gene that confer resistance to DMI inhibitors, where the mutations are L50S, D134G, V136A / C, Y137F, S188N, A379G, I381V, deletions 459-460, Y461H / S, N513K, and S524T. The main sources are www.frac.info, Cools et al., Plant Pathol (2013) 62:36-42 and Schmitz HK et al., Pest Manag Sci (2014) 70:378-388.

[0105] Therefore, in preferred embodiments, a compound of formula (I) (including any one of the compounds listed in Table 2 (below)) or a fungicidal composition according to the present invention comprising a compound of formula (I) is used to control fungal and mold strains that are resistant to one or more fungicidal agents from any of the following fungicidal and fungicidal MoA classes: quinone external inhibitors (QoI), quinone internal inhibitors (QiI), succinate dehydrogenase inhibitors (SDHI), and sterol demethylation inhibitors (DMI).

[0106] As used herein, the term “habitat” means a field where plants are growing, or where the seeds of cultivated plants are sown, or where the seeds will be sown in the soil. This includes the soil, seeds and seedlings, and established vegetation.

[0107] The term "plant" refers to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, stalks, foliage, and fruits.

[0108] The term “plant reproductive body” is understood to refer to the reproductive parts of a plant, such as seeds, that can be used for propagation, as well as vegetative bodies such as cuttings or tubers, such as those of potatoes. Examples include seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes, and parts of the plant. Also included are germinated plants and sprouts that will be transplanted after germination or after emerging from the soil. These sprouts may be protected by complete or partial treatment by immersion before transplanting. Preferably, “plant reproductive body” is understood to refer to seeds.

[0109] Pest control agents referred to herein by their common names are publicly known, for example, from “The Pesticide Manual”, 15th Ed., British Crop Protection Council 2009.

[0110] Compounds of formula (I) may be used in their original form or, preferably, in combination with auxiliaries readily available in the field of formulation. For this purpose, they may be readily incorporated in known forms into emulsifying concentrates, coating pastes, directly sprayable or dilutable solutions or suspensions, dilutable emulsions, wettable powders, soluble powders, powders, granular materials and, for example, capsules in polymeric substances. As with the type of composition, the method of application, such as spraying, atomizing, powdering, scattering, coating or pouring, is selected according to the intended purpose and the circumstances at the time. The composition may also contain further auxiliaries such as stabilizers, defoamers, viscosity modifiers, binders or adhesives and fertilizers, sources of trace elements or other formulations for obtaining special effects.

[0111] For example, suitable carriers and auxiliaries used in agriculture may be solids or liquids and are useful substances in compounding technology, such as natural or recycled mineral substances, solvents, dispersants, wetting agents, adhesives, thickeners, binders, or fertilizers. Such carriers are described, for example, in International Publication No. 97 / 33890.

[0112] The compound of formula (I) is usually used in the form of a composition and may be applied simultaneously with or sequentially to a crop area or plant to be treated with further compounds. These further compounds may be, for example, fertilizers or trace element donors or other preparations that affect plant growth. These may also be selective or non-selective herbicides and insecticides, fungicides, fungicides, nematicides, mollusk repellents, or mixtures of these preparations, which may include further carriers, surfactants, or application enhancers that are conventionally used in the field of formulations as needed.

[0113] The compounds of formula (I) may be used in the form of a (fungicide / fungicide) composition for the control or protection of plant pathogenic microorganisms, comprising at least one compound of formula (I) as an active ingredient, or in the form of at least one preferred individual compound as defined above, in free form or in agrochemically usable salt form, and at least one of the above-mentioned auxiliary agents.

[0114] The present invention provides a composition, preferably a fungicidal and fungicidal composition, comprising at least one compound of formula (I), an agriculturally acceptable carrier, and optionally an auxiliary agent. The agriculturally acceptable carrier is, for example, a carrier suitable for agricultural use. Agricultural carriers are well known in the art. Preferably, the composition may, in addition to the compound of formula (I), contain at least one or more compounds that are active in controlling pests, such as additional fungicidal and fungicidal active ingredients.

[0115] The compound of formula (I) may be the sole active ingredient in a composition, or, where appropriate, may be mixed with one or more additional active ingredients such as pest control agents, fungicides, synergists, herbicides, or plant growth regulators. These additional active ingredients may, in some cases, result in unexpected synergistic activity.

[0116] Examples of suitable additional active ingredients include the following: acyl amino acid fungicides, aliphatic nitrogen fungicides, amide fungicides, anilide fungicides, antibiotic fungicides, aromatic fungicides, arsenic fungicides, arylphenyl ketone fungicides, benzamide fungicides, benzanilide fungicides, benzimidazole fungicides, benzothiazole fungicides, and botanical fungicides. Mold killer, cross-linked diphenyl fungicide, carbamate fungicide, carvanilate fungicide, conazole fungicide, copper fungicide, dicarboximide fungicide, dinitrophenol fungicide, dithiocarbamate fungicide, dithiolane fungicide, flamido fungicide, flanilide fungicide, hydrazide fungicide, imidazole fungicide, mercury fungicide, Morpholine fungicide, organophosphate fungicide, organotin fungicide, oxathiin fungicide, oxazole fungicide, phenylsulfamide fungicide, polysulfide fungicide, pyrazole fungicide, pyridine fungicide, pyrimidine fungicide, pyrrole fungicide, quaternary ammonium fungicide, quinoline fungicide, quinone fungicide, quinoxaline fungicide Examples include fungicides, strobilurin fungicides, sulfonanilide fungicides, thiadiazole fungicides, thiazole fungicides, thiazolidine fungicides, thiocarbamate fungicides, thiophene fungicides, triazine fungicides, triazole fungicides, triazolopyrimidine fungicides, urea fungicides, valineamide fungicides, and zinc fungicides.

[0117] Examples of suitable additional active ingredients also include: petroleum, 1,1-bis(4-chlorophenyl)-2-ethoxyethanol, 2,4-dichlorophenylbenzenesulfonate, 2-fluoro-N-methyl-N-1-naphthylacetamide, 4-chlorophenylphenylsulfone, acetoprole, aldoxycarb, amidithione, amidethioate, amiton, hydrogen oxalate, amitraz, aramite, arsenic trioxide, azobenzene, azothoate, benomyl, benoxaphos, benzyl benzoate Bixafen, brofenvalerate, bromocyclene, bromophos, bromopropylate, buprofezin, butocarboxime, butoxycarboxime, butylpyridaben, calcium polysulfide, campechlor, carbanolate, carbophenothione, simiazole, quinomethionato, chlorbenside, chlordimeform, chlordimeform hydrochloride, chlorphenetol, chlorfensone, chlorfensulfide, chlorobenzilate, chloromebform, chloromethionone, chloropro Pyrate, Chlorthiofos, Synerin I, Synerin II, Synerin, Closantel, Coumaphos, Crotamiton, Clothoxyfos, Cufraneb, Cyanthoate, DCPM, DDT, Demefion, Demefion-O, Demefion-S, Demeton-Methyl, Demeton-O, Demeton-O-Methyl, Demeton-S, Demeton-S-Methyl, Demeton-S-Methylsulfone, Diclofluanide, Dichlorvos, Dicrifos, Dienochlor, Dimefox, Dynex, Dynex-Dicrexin, Dinocat Pu-4, Dinocap-6, Dinoctone, Dinopenton, Dinosulfone, Dinotervon, Dioxathion, Diphenylsulfone, Disulfiram, DNOC, Dofenapine, Doramectin, Endothion, Eprinomectin, Ethoate-methyl, Etrimphos, Phenazaflor, Fenbutasin oxide, Phenothiocarb, Fenpyrad, Fenpyroximate, Fenpyrazamine, Fenson, Fentriphanil, Flubendimine, Flucycloxurone, Fluenetil, Fluolbenside, FMC 1137, Formetanate, Formetanate hydrochloride, Formparanate, γ-HCH, Gliodin, Halfenprox, Hexadecylcyclopropane carboxylate, Isocarbophos, Jasmolin I, Jasmolin II,Iodophenphos, Lindan, Malonoben, Mecarbam, Mephosphoran, Mesulfen, Methacryphos, Methyl bromide, Metolcarb, Mexacarbate, Milbemycin oxime, Mipahox, Monoclotophos, Morphothion, Moxidectin, Nared, 4-Chloro-2-(2-Chloro-2-methylpropyl)-5-[(6-iodo-3-pyridyl)methoxy]pyridazin-3-one, Niflulidide, Nicomycin, Nitrilacarb, Nitrilacarb 1:1 zinc chloride complex, Omethoate, Oxydeprophos, Oxydisulfone, pp'-DDT, Pa Lathion, permethrin, fencapton, phosalon, phosphoran, phosphamidone, polychloroterpenes, polynactin, proclonal, promacil, propoxer, protidathion, protoate, pyrethrin I, pyrethrin II, pyrethrin, pyridafenthion, pyrimitate, quinalphos, quinthiokis, R-1492, phosglycine, rotenone, shlardan, sebuphos, selamectin, sofamide, SSI-121, sulfiram, sulfuramide, sulfotep, sulfur, diflovidazine, τ-fluvalinate, TEPP, terbam, teto Radiphon, Tetrasul, Thiafenox, Thiocarboxim, Thiofanox, Thiometon, Thioquinox, Turingiencin, Triamiphos, Triatene, Triazophos, Triazurone, Triphenophos, Trinactin, Bamidthion, Vaniliprole, Bethoxazine, Copper Dioctanonate, Copper Sulfate, Sibutrin, Diclofen, Dichlorophene, Endotar, Fetin, Slaked Lime, Narbam, Quinoclamine, Quinonamide, Simazine, Triphenyltin Acetate, Triphenyltin Hydroxide, Culfomate, Piperazine, Thiophanate, Chloralose, Fenthione, pyridine-4-amine, strychnine, 1-hydroxy-1H-pyridine-2-thione, 4-(quinoxaline-2-ylamino)benzenesulfonamide, 8-hydroxyquinoline sulfate, bronopol, copper hydroxide, cresol, dipyrithione, dodicine, phenaminosulf, formaldehyde, hydrargafen, kasugamycin, kasugamycin hydrochloride hydrate, nickel bis(dimethyldithiocarbamate), nitrapyrine, octylinone, oxolinic acid, oxytetracycline, potassium hydroxyquinoline sulfate, probenazole,Streptomycin, streptomycin sesquisulfate, tecrophthalam, thiomersal, Adoxophyes orana GV, Agrobacterium radiobacter, species of Amblyseius, Anagrapha falcifera NPV, Anagrus atomus, Aphelinus abdominalis, Aphidius colemani, Aphidoletes aphidimyza, Autographa californica NPV, Bacillus sphaericus Neide, Beauveria brongniartii, Chrysoperla Carnea), Red-toothed ladybug (Cryptolaemus montrouzieri), Codling moth (Cydia pomonella) GV, Leaf-mining parasitic wasp (Dacnusa sibirica), Diglyphus isaea, Greenhouse parasitic wasp (Encarsia formosa), Desert parasitic wasp (Eretmocerus eremicus), Heterorhabditis bacteriophora and H. megidis, Rope-legged ladybug (Hippodamia convergens), Long-horned parasitic wasp (Leptomastix dactylopii), Macrolophus caliginosus, Armyworm (Mamestra) brassicae) NPV, Metaphycus helvolus, Metarhizium anisopliae var. acridum, Metarhizium anisopliae var. anisopliae,Pine sawfly (Neodiprion sertifer) NPV and N. lecontei NPV, species of the genus Orius, Paecilomyces fumosoroseus, Chilean predatory mite (Phytoseiulus persimilis), Steinernema bibionis, Steinernema carpocapsae, Steinernema feltiae, Steinernema glaseri, Steinernema riobrave, Steinernema riobravis, Steinernema mascapteris Species of the genus Steinernema (scapterisci), species of the genus Steinernema, species of the genus Trichogramma, Typhlodromus occidentalis, Verticillium lecani (lecanii), aphorate, bisadilyl, busulfan, dimatif, hemel, hempa, metepa, methiotepa, methyl aphorate, molzide, penflurone, tepa, thiohempa, thiotepa, tretamine, uredepa, (E)-deca-5-en-1-yl acetate + (E)-deca-5-en-1-ol, (E)-trideca-4-en-1-yl acetate, (E)-6-methylhepta-2-en-4-ol, (E,Z)-tetradeca-4,10-dien-1-yl acetate, (Z)-dodeca-7-en-1-yl Acetate, (Z)-Hexadeca-11-Enal, (Z)-Hexadeca-11-En-1-Ilacetate, (Z)-Hexadeca-13-En-11-In-1-Ilacetate, (Z)-Icosa-13-En-10-On, (Z)-Tetradeca-7-En-1-R, (Z)-Tetradeca-9-En-1-All, (Z)-Tetradeca-9-En-1-Ilacetate, (7E,9Z)-Dodeca-7,9-Dien-1-Ilacetate, (9Z,11E)-Tetradeca-9,11-Dien-1-Ilacetate,(9Z,12E)-Tetradeca-9,12-diene-1-ylacetate, 14-methyloctadeca-1-ene, 4-methylnonan-5-ol + 4-methylnonan-5-one, α-multistriatin, Brevicomin, Kodrelua, Kodremon, Kyurua, Disparua, Dodeca-8-en-1-ylacetate, Dodeca-9-en-1-ylacetate, Dodeca-8,10-diene-1-ylacetate, Dominicalua, 4-methyloctanoate ethyl, Eugenol, Frontalin, Grandlua, Grandlua I, Grandlua II, Grandl A III, Grandlua IV, Hexalua, Ipsdienol, Ipsenol, Japonilua, Lineatin, Littleua, Lupulua, Medlua, Megatomoic acid, Methyl eugenol, Muscarua, Octadeca-2,13-dien-1-ylacetate, Octadeca-3,13-dien-1-ylacetate, Orfuralua, Orictalua, Ostramon, Siglua, Solzidine, Sulcatol, Tetradeca-11-en-1-ylacetate, Trimedlua, Trimedlua A, Trimedlua B1, Trimedlua B2, Trimedlua C, Trunk-Col (tr unc-call), 2-(octylthio)ethanol, butopyrronoxyl, butoxy(polypropylene glycol), dibutyl adipate, dibutyl phthalate, dibutyl succinate, diethyltoluamide, dimethyl carbate, dimethyl phthalate, ethylhexanediol, hexaamide, methquin-butyl, methylneodecanamide, oxamate, picaridin, 1-dichloro-1-nitroethane, 1,1-dichloro-2,2-bis(4-ethylphenyl)ethane, 1,2-dichloropropane + 1,3-dichloropropene, 1-bromo-2-chloroethane , 2,2,2-trichloro-1-(3,4-dichlorophenyl)ethyl acetate, 2,2-dichlorovinyl 2-ethyl sulfinylethyl methyl phosphate, 2-(1,3-dithiolan-2-yl)phenyldimethyl carbamate, 2-(2-butoxyethoxy)ethyl thiocyanate, 2-(4,5-dimethyl-1,3-dioxolan-2-yl)phenyl methyl carbamate, 2-(4-chloro-3,5-xylyloxy)ethanol, 2-chlorovinyl diethyl phosphate, 2-imidazolidone, 2-isovalerylindan-1,3-dione,2-Methyl(propa-2-inyl)aminophenylmethylcarbamate, 2-thiocyanatoethyl laurate, 3-bromo-1-chloropropa-1-ene, 3-methyl-1-phenylpyrazole-5-yldimethylcarbamate, 4-methyl(propa-2-inyl)amino-3,5-xy, Lylmethylcarbamate, 5,5-dimethyl-3-oxocyclohexa-1-enyldimethylcarbamate, acetylone, acrylonitrile, aldrin, allosamidin, alixicarb, α-ecdysone, aluminum phosphide, aminocarb, anabasine, atidathion, azamethiphos, Bacillus thuringiensis delta-endotoxin, barium hexafluorosilicate, barium polysulfide, bartholin, Bayer 22 / 190, Bayer 22408, β-cyfluthrin, β-cypermethrin, bioetanomethrin, biopermethrin, bis(2-chloroethyl) ether, borax, bromfenbinphos, bromo-DDT, bufencarb, butacarb, butathiophos, butonate, calcium arsenate, calcium cyanide, carbon disulfide, carbon tetrachloride, cartap hydrochloride, sebadin, chlorbicyclene, chlordan, chlordecone, chloroform, chloropicrin, chlorphoxime, chlorprazophos, cis-resmethrin, cismethrin, crocitrin, copper acetoarsenite, copper arsenate, copper oleate, cumithoate, cryolite, CS 708, cyanophenphos, cyanophos, ciclethrin, cythioato, d-tetramethrin, DAEP, dazomet, decarbofuran, diamidaphos, dikapton, diclofenthion, diclesyl, dicyclanil, dierudrin, diethyl 5-methylpyrazole-3-yl phosphate, dirol, dimefluthrin, dimethane, dimethrin, dimethylvinphos, dimethilane, dinoprop, dinosam, dinoseb, diofenolan, dioxabenzophos, diticlophos, DSP, ecdysterone, EI 1642, EMPC, EPBP, Etaphos, Ethiofencarb, Ethyl formate, Ethylene dibromide, Ethylene dichloride, Ethylene oxide, EXD, Fenchlorphos, Phenetacarb, Fenitrothion, Phenoxacrim, Fenpyritrin, Fensulfothion, Fenthion-ethyl, Flucoflon, Fosmethilane, Fospilate, Phosthiethane, Frathiocarb, Frethrin, Guazatin, Guazatin acetate, Sodium tetrathiocarbonate, Halfenprox, HCH, HEOD, Heptachlor, Heterophos, HHDN, Hydrogen cyanide, Hikincarb, IPSP, Isazofos, Isobenzane, Isodrine,Isofenphos, Isolane, Isoprothiolane, Isoxathion, Juvenile Hormone I, Juvenile Hormone II, Juvenile Hormone III, Kereban, Quinoprene, Lead Arsenate, Leptophos, Lilimphos, Litidathion, m-Cumenyl Methylcarbamate, Magnesium Phosphate, Magidox, Mecarfone, Menazone, Mercurous Chloride, Mesulfenphos, Metam, Metam-Potassium, Metam-Sodium, Methanesulfonyl Fluoride, Metochlortophos, Methoprene, Methotrin, Methoxychloride, Methylisothiocyanate, Methylchloroform, Methylene Chloride, Methoxadiazone, Millet Calcium, naphthalophos, naphthalene, NC-170, nicotine, nicotine sulfate, nithiazine, nornicotine, O-5-dichloro-4-iodophenyl O-ethylethyl phosphonothioate, O,O-diethyl O-4-methyl-2-oxo-2H-chromen-7-yl phosphorothioate, O,O-diethyl O-6-methyl-2-propylpyrimidine-4-yl phosphorothioate, O,O,O',O'-tetrapropyldithiopyrophosphate, oleic acid, para-dichlorobenzene, parathion-methyl, pentachlorophenol, pentachlorophenyl laurate, pH 60-38, Fencapton, Fosnikrol, Phosphine, Foxime-methyl, Pyrimethaphos, Polychlorodicyclopentadiene isomer, Potassium arsenite, Potassium thiocyanate, Precosen I, Precosen II, Precosen III, Primidophos, Profluthrin, Promecarb, Prothiophos, Pyrazophos, Pyrethmetrin, Quassia, Quinalphos-methyl, Quinothion, Rahoxanide, Resmethrin, Rotenone, Cadetrin, Lianya, Lianodine, Sabajira), Shuradan, Sebuphos, SI-0009, Thiapronil Sodium arsenite, sodium cyanide, sodium fluoride, sodium hexafluorosilicate, sodium pentachlorophenoxide, sodium selenite, sodium thiocyanate, sulcoflon, sulcoflon-sodium, sulfuryl fluoride, sulpros, tar oil, tadimucarb, TDE, tebupyrimphos, temephos, terarethrin, tetrachloroethane, cyclamus, thiocyclamus hydrogen oxalate, thionazine, thiosultap, thiosultap-sodium, tralomethrin, transpermethrin,Triazamate, trichlormetaphos-3, trichloronate, trimetacarb, tolprocarb, triclopyricarb, triprene, veratridine, veratrin, XMC, ζmethrin, zinc phosphide, zolaprofos and meperfluthrin, tetramethylfluthrin, bis(tributyltin) oxide, bromoacetamide, ferric phosphate, niclosamide-olamine, tributyltin oxide, pyrimorph, triphenmorph, 1,2-dibro Mo-3-chloropropane, 1,3-dichloropropene, 3,4-dichlorotetrahydrothiophene 1,1-dioxide, 3-(4-chlorophenyl)-5-methylrhodanine, 5-methyl-6-thioxo-1,3,5-thiadiadinane-3-ylacetic acid, 6-isopentenylaminopurine, anisifurupurine, benkrothiaz, cytokinin, DCIP, furfural, isamidophos, kinetin, mulberry dark spot disease fungus (Myrothecium verrucaria) composition, tetrachlorothiophene, xylenol, zeatin, potassium ethylxanthogenic acid, acibenzolar, acibenzolar-S-methyl, Japanese knotweed (Reynoutria japonica) Sachalinensis extract, α-chlorohydrin, anthus, barium carbonate, bisthiosemi, brodiphacomum, bromadiolon, bromethalin, chlorophacinone, cholecalciferol, coumacrol, coumafuryl, coumatetralyl, crimidine, diphenacum, difethiaron, diphacinone, ergocalciferol, fulocumafen, fluoroacetamide, flupropazine, flupropazine hydrochloride, norbormid, fosacetim, phosphorus, pidomone, pyrinulone, siriloside, sodium fluoroacetate, thallium sulfate, warfarin, 2-(2-butoxyethoxy)ethylpiperonilate, 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohexa-2-enone, farnesol + nerolidol, berbutin, MGK 264, piperonyl butoxide, piprotal, propyl isomer, S421, sesamex, sesamolin, sulfoxide, anthraquinone, copper naphthenate, copper oxychloride, dicyclopentadiene, thyram, zinc naphthenate, ziram, imanin, ribavirin, chloroinconazide, mercuric oxide, thiophanate-methyl, azaconazole, vitertanol, bromconazole,Cyproconazole, difenoconazole, diniconazole, epoxyconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafole, flametopyr, hexaconazole, imazalil, imibenconazole, ipconazole, metconazole, mycrobutanil, paclobutrazol, pefurazoate, penconazole, prothioconazole, pyrifenox, prochloraz, propiconazole, pyrisoxazole, simeconazole, tebuconazole, tetraconazole, triadimephon, triadimenol, triflumizol L, triticonazole, ancimidor, phenalimol, nualimol, bupirimate, dimethirimol, ethirimol, dodemorph, fenpropidine, fenpropimorph, spiroxamine, tridemorph, cyprodinil, mepanipyrim, pyrimethanil, fenpiclonil, fludioxonil, venalaxyl, flaraxyl, metalaxyl, R-metalaxyl, offlace, oxadixyl, carbendazim, debacarb, fuberidazole, thiabendazole, clozolinate, diclozolin, microzolin, procymidone, vinclozolin, boscali D, Carboxyne, Fenflam, Flutolanil, Mepronil, Oxycarboxyne, Penthiopyrad, Tifluzamide, Dozin, Iminoctadine, Azoxystrobin, Dimoxystrobin, Enestrobrin, Phenaminestrobin, Fluphenoxystrobin, Fluoxastrobin, Kresoxim-methyl, Metominostrobin, Trifloxystrobin, Oryzastrobin, Picoxystrobin, Pyraclostrobin, Pyrametstrobin, Pyramoxystrobin, Ferubam, Mancozeb, Maneb, Methylam, Propineb, Zineb, Captafo Lu, Captan, Fluorimide, Holpet, Trilfluanide, Bordeaux mixture, Copper oxide, Mankapper, Oxycopper, Nitrotal-isopropyl, Edifenphos, Iprobenphos, Phosdiphen, Torukurophos-methyl, Anirazine, Benciavaricarb, Blastocydin-S, Chloroneb, Chlorothalonil, Cyflufenamid, Cymoxanil, Cyclobtrifluram, Diclocimet, Diclomazine, Dichloran, Dietofencarb, Dimethomorph, Flumorph, Dithianone, Etaboxam, Etridiazole, Famoxadone, Phenamidon,Phenoxanil, felimzon, fluazinam, flumethylsulfolim, fluopicolide, fluoxythioconazole, flusulfamide, fluxapyroxade, fenhexamide, fosetyl-aluminum, himexazole, iprovalicarb, cyazofamide, metasulfocarb, metraphenone, pencyclon, phthalide, polyoxin, propamoclav, pyribencarb, proquinazide, pyroquilon, pyriophenone, quinoxyfen, quintozen, thiadinyl, triazoxide, tricyclazole, triforine, baridama Icin, Valifenarate, Zoxamide, Mandipropamide, Flubeneteram, Isopyrazam, Sedaxane, Benzovindiflupir, Pidiflumetofen, 3-Difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (3',4',5'-trifluorobiphenyl-2-yl)amide, Isoflucipram, Isothianil, Dipimethitron, 6-Ethyl-5,7-Dioxo-pyrrolo[4,5][1,4]dithiino[1,2-c]isothiazol-3-carbonitride, 2-(Difluoromethyl)-N-[3-ethyl- 1,1-dimethylindan-4-yl]pyridine-3-carboxamide, 4-(2,6-difluorophenyl)-6-methyl-5-phenylpyridazine-3-carbonitrile, (R)-3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide, 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-2,5-dimethylpyrazole-3-amine, 4-(2-bromo-4-fluorophenyl)-N-(2-chloro- 6-Fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, Fluindapyr, Cumethoxystrobin (Jiaxiangjunzhi), Rubenmixianan, Diclobentiazox, Mandestrobin, 3-(4,4-Difluoro-3,4-Dihydro-3,3-dimethylisoquinoline-1-yl)quinolone, 2-[2-Fluoro-6-[(8-Fluoro-2-methyl-3-quinolyl)oxy]phenyl]propan-2-ol, Oxathiapiproline,tert-butyl N-[6-[[[(1-methyltetrazole-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate, pyraziflumid, impulfluxam, tolprocarb, mefentrifluconazole, ibufentrifluconazole, 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethylindan-4-yl]pyridine-3-carbo, Xamide, N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methyl-formamidine, N'-[4-(4,5-dichlorothiazole-2-yl)oxy-2,5-dimethylphenyl]-N-ethyl-N-methyl-formamidine, [2-[3-[2-[1-[2-[3,5-bis(difluoromethyl)pyrazole-1-yl]acetyl]-4-piperidyl]thiazole-4-yl]-4,5-dihydroisoxazole-5-yl]-3-chlorophenyl]methanesulfonate, buta-3-inyl N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate, methyl N-[[5-[4-(2,4-dimethylphenyl)triazole-2-yl]-2-methyl-phenyl]methyl]carbamate, 3-chloro-6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine, pyridaclomethyl, 3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyrazole-4-carboxami D, 1-[2-[[1-(4-chlorophenyl)pyrazole-3-yl]oxymethyl]-3-methylphenyl]-4-methyltetrazol-5-one, 1-methyl-4-[3-methyl-2-[[2-methyl-4-(3,4,5-trimethylpyrazole-1-yl)phenoxy]methyl]phenyl]tetrazol-5-one, aminopyrifen, ametoctrazine, amisulbrom, penflufen, (Z,2E)-5-[1-(4-chlorophenyl)pyrazole-3-yl]oxy-2-methoxyimino-N,3-dimethyl -Penta-3-enamide, Florylpicoxamide, Fenpicoxamide, Metallylpicoxamide, Tebufloxin, Ipfluphenoquin, Quinofumeline, Isofetamide, N-[2-[2,4-dichlorophenoxy]phenyl]-3-(difluoromethyl)-1-methylpyrazole-4-carboxamide, N-[2-[2-chloro-4-(trifluoromethyl)phenoxy]phenyl]-3-(difluoromethyl)-1-methylpyrazole-4-carboxamide, Benzothiostrobin, Phenamacryl, 5-amino-1,3,4-Thiadianazole-2-thiol zinc salt (2:1), fluopyram, fluphenoxadiazam, fluthianil, fluopimomid, pyrapropoin, picarbutrazox, 2-(difluoromethyl)-N-(3-ethyl-1,1-dimethylindan-4-yl)pyridine-3-carboxamide, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylindan-4-yl)pyridine-3-carboxamide, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazole-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, methyltetraprole, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylindan-4-yl)pyridine-3-carboxamide Luboxamide, α-(1,1-dimethylethyl)-α-[4'-(trifluoromethoxy)[1,1'-biphenyl]-4-yl]-5-pyrimidine methanol, fluoxapiproline, enoxastrobin, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazole-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-sulfanyl-1,2,4-triazole-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thioxo-4H-1,2,4-Triazole-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, Trinexapac, chemoxystrobin, zhongshengmycin, thiodiazole copper, zinc thiazole, amectotractin, iprodione, sevoctilamine, N'-[5-bromo-2-methyl-6-[(1S)-1-methyl-2-propoxyethoxy]-3-pyridyl]- N-ethyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-6-[(1R)-1-methyl-2-propoxyethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxyethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-chloro-2-methyl-6-(1- [Methyl-2-propoxyethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxyethoxy)-3-pyridyl]-N-isopropyl-N-methyl-formamidine (These compounds can be prepared by the method described in International Publication No. 2015 / 155075); N'-[5-bromo-2-methyl-6-(2-propoxypropoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine (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-phenylethyl)phenyl]-N-methyl-formamidine, N'-[4-(1-cyclopropyl-2,2,2-trifluoro-1-hydroxy-ethyl)-5-methoxy-2-methyl-phenyl]-N-isopropyl-N-methyl-formamidine (These compounds can be prepared by the method described in International Publication No. 2018 / 228896); N-ethyl-N'-[5-methoxy-2-methyl-4-[(2-trifluoromethyl)oxetane-2-yl]phenyl]-N-methyl-formamidine, N-ethyl-N'-[5-methoxy-2-methyl-4-[(2-trifluoromethyl] (Luoromethyl)tetrahydrofuran-2-yl]phenyl]-N-methyl-formamidine (These compounds can be prepared by the method described in International Publication No. 2019 / 110427); N-[(1R)-1-benzyl-3-chloro-1-methylbuta-3-enyl]-8-fluoroquinoline-3-carboxamide, N-[(1S)-1-benzyl-3-chloro-1-methylbuta-3-enyl]-8-fluoroquinoline-3-carboxamide, N-[(1R) N-1-benzyl-3,3,3-trifluoro-1-methylpropyl]-8-fluoroquinoline-3-carboxamide, N-[(1S)-1-benzyl-3,3,3-trifluoro-1-methylpropyl]-8-fluoroquinoline-3-carboxamide, N-[(1R)-1-benzyl-1,3-dimethylbutyl]-7,8-difluoroquinoline-3-carboxamide, N-[(1S)-1-benzyl-1,3-dimethylbutyl]-7,8-difluoro -Quinoline-3-carboxamide, 8-Fluoro-N-[(1R)-1-[(3-fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide, 8-Fluoro-N-[(1S)-1-[(3-fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide, N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-8-fluoroquinoline-3-carboxamide, N-[(1S)-1-benzyl-1,3-Dimethyl-butyl]-8-fluoroquinoline-3-carboxamide, N-((1R)-1-benzyl-3-chloro-1-methylbuta-3-enyl)-8-fluoroquinoline-3-carboxamide, N-((1S)-1-benzyl-3-chloro-1-methylbuta-3-enyl)-8-fluoroquinoline-3-carboxamide (These compounds can be prepared by the method described in International Publication No. 2017 / 153380); 1-(6,7-dimethylpyrazolo[1,5-a]pyridine-3-yl)-4,4,5-trifluoro-3 ,3-dimethylisoquinoline, 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,6-trifluoro-3,3-dimethylisoquinoline, 4,4-difluoro-3,3-dimethyl-1-(6-methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline, 4,4-difluoro-3,3-dimethyl-1-(7-methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline, 1-(6-chloro-7-methylpyrazolo[1,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dimethyl- Isoquinolines (these compounds can be prepared by the method described in International Publication No. 2017 / 025510); 1-(4,5-dimethylbenzimidazole-1-yl)-4,4,5-trifluoro-3,3-dimethylisoquinoline, 1-(4,5-dimethylbenzimidazole-1-yl)-4,4-difluoro-3,3-dimethylisoquinoline, 6-chloro-4,4-difluoro-3,3-dimethyl-1-(4-methylbenzimidazole-1-yl)isoquinoline, 4,4-difluoro-1-(5-fluoro-4-methylben Zoimidazole-1-yl)-3,3-dimethylisoquinoline, 3-(4,4-difluoro-3,3-dimethyl-1-isoquinolyl)-7,8-dihydro-6H-cyclopenta[e]benzimidazole (these compounds can be prepared by the method described in International Publication No. 2016 / 156085); N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide, N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]propanamide, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 1-Methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, 3-ethyl-1 -Methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl ]phenyl]methyl]isoxazolidine-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]-1,2,4-triazole-3-amine (These compounds are described in International Publication No. 2017 / 055473, International Publication No. 2017 / 055469, International Publication No. 2017 / 093348 and National Publication No. It can be prepared by the method described in International Publication No. 2017 / 118689); 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazole-1-yl)propan-2-ol (This compound can be prepared by the method described in International Publication No. 2017 / 029179); 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazole-1-yl)propan-2-ol (This compound can be prepared by the method described in International Publication No. 2017 / 0291, It can be prepared by the method described in publication 79); 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxy-propyl]imidazole-4-carbonitriel (This compound can be prepared by the method described in International Publication 2016 / 156290); 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxy-propyl]imidazole-4-carbonitriel (This compound can be prepared by the method described in International Publication 2016 / 156290) It can be prepared by the method described below; (4-phenoxyphenyl)methyl 2-amino-6-methylpyridine-3-carboxylate (this compound can be prepared by the method described in International Publication No. 2014 / 006945); 2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetron (this compound can be prepared by the method described in International Publication No. 2011 / 138281); N-methyl-4-[5-(trifluoromethyl (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazole-3-yl]benzenecarbothioamide; N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]benzamide; (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazole-3-yl]oxy-2-methoxyimino-N,3-dimethyl-penta-3-enamide (this compound can be prepared by the method described in International Publication No. 2018 / 153707); N'-(2-chloro-5-methyl-4-phenoxy-phenyl Nyl)-N-ethyl-N-methyl-formamidine; N'-[2-chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidine (this compound may be prepared by the method described in International Publication No. 2016 / 202742); 2-(difluoromethyl)-N-[(3S)-3-ethyl-1,1-dimethylindan-4-yl]pyridine-3-carboxamide (this compound may be prepared by the method described in International Publication No. 2014 / 095675);(5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone, (3-methylisoxazole-5-yl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methanone (These compounds can be prepared by the method described in International Publication No. 2017 / 220485); 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide (This compound can be prepared by the method described in International Publication No. 2018 / 065414); ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate (This compound can be prepared by the method described in International Publication No. 2018 / 158365); 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]acetamide, N-[(E)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]benzamide, N-[(Z)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]benzamide, N-[N-methoxy-C-methyl-carbonimidoyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]benzamide (These compounds can be prepared by the method described in International Publication No. 2018 / 202428).

[0118] The compounds of the present invention may also be used in combination with anthelmintic agents. Such anthelmintic agents include compounds selected from the macrocyclic lactone class of compounds such as ivermectin, avermectin, abamectin, emamectin, epirinomectin, doramectin, selamectin, moxidectin, nemadectin, and milbemycin derivatives, as described in European Patent No. 357460, European Patent No. 444964, and European Patent No. 594291. Additional anthelmintic agents include semi-synthetic and biosynthetic avermectin / milbemycin derivatives, such as those described in U.S. Patent No. 5015630, International Publication No. 9415944, and International Publication No. 9522552. Additional anthelmintic agents include benzimidazoles such as albendazole, cambendazole, fenbendazole, flubendazole, mebendazole, oxyfendazole, oxybendazole, parbendazole, and other components of this class. Additional anthelmintics include tetrahydropyrimidines such as imidazothiazole, tetramisol, levamisole, pyrantel pamoate, oxantel, or morantel. Additional anthelmintics include fluxides such as triclabendazole and chlorthrone, and cestocides such as praziquantel and epsiplantel.

[0119] The compounds of the present invention can be used in combination with derivatives and analogues of paraherquamid / marcfortin class anthelmintics and antiparasitic oxazolines, such as those disclosed in U.S. Patent No. 5,478,855, U.S. Patent No. 4,639,771 and German Patent No. 1,9520,936.

[0120] The compounds of the present invention can be used in combination with derivatives and analogues of the general class of dioxomorpholine antiparasitic agents described in International Publication No. 9615121, and in combination with anthelmintic cyclic depsipeptides such as those described in International Publication No. 9611945, International Publication No. 9319053, International Publication No. 9325543, European Patent No. 626375, European Patent No. 382173, International Publication No. 9419334, European Patent No. 382173, and European Patent No. 503538.

[0121] The compounds of the present invention can be used in combination with other exocaridetic agents; for example, fipronil; pyrethroids; organophosphate esters; insect growth regulators such as lufenuron; ecdysone agonists such as tebufenozide; and neonicotinoids such as imidacloprid.

[0122] The compounds of the present invention are, for example, terpene alkaloids, such as those described in International Publication No. 95 / 19363 or International Publication No. 04 / 72086, and can be used in combination with the compounds disclosed therein.

[0123] Other examples of such biologically effective compounds in which the compounds of the present invention can be used in combination include, but are not limited to, the following: Organophosphate esters: acephate, azamethiphos, adinphos-ethyl, adinphos-methyl, bromophos, bromophos-ethyl, kazusaphos, chlorethoxyphos, chlorpyrifos, chlorfenbinphos, chlormephos, demeton, demeton-S-methyl, demeton-S-methylsulfone, dialiphos, diazinon, dichlorvos, diclotophos, dimethoate, disulfon, ethione, etoprophos, etrimphos, fanfar, phenamiphos, fenitrothion, fensulfothion, fenthion, flupyrazophos, phonophos, formothion, fostiazate, heptenophos, isazofos, isothioate, isoxathio Malathion, methacryphos, methamidophos, methidathion, methyl-parathion, mevinphos, monoclotophos, naled, omethoate, oxydemeton-methyl, paraoxone, parathion, parathion-methyl, fenthoate, phosalon, phospholan, phosphocarb, phosmet, phosphamidone, pholate, foxim, pirimiphos, pirimiphos-methyl, profenophos, propaphos, proetamphos, prothiophos, pyraclophos, pyridapention, quinalphos, sulprophos, temephos, terbuphos, tebupyrimphos, tetrachlorvinphos, thimeton, triazophos, trichlorfon, bamidothion.

[0124] Carbamates: Alanicarb, Aldicarb, 2-sec-butylphenylmethylcarbamate, Benfuracarb, Carbaryl, Carbofuran, Carbosulfan, Chloetocarb, Ethiophencarb, Phenoxycarb, Fenthiocarb, Frathiocarb, HCN-801, Isoprocarb, Indoxacarb, Methiocarb, Methomyl, 5-Methyl-m-cumenylbutyryl(methyl)carbamate, Oxamyl, Pyrimicab, Propoxul, Thiodicarb, Thiofanox, Triazamate, UC-51717.

[0125] Pyrethroids: acrinathin, arethrin, alphametrin, 5-benzyl-3-furylmethyl(E)-(1R)-cis-2,2-dimethyl-3-(2-oxothiolane-3-ylidenemethyl)cyclopropanecarboxylate, bifenthrin, β-cyfluthrin, cyfluthrin, α-cypermethrin, β-cypermethrin, bioarethrin, bioarethrin ((S)-cyclopentyl isomer), biorethmetrin, bifenthrin, NCI-85193, cycloprothrin, cyhalothrin Citrine, cyphenothrine, deltamethrine, empenthrine, esfenvalerate, etofenprox, fenfluthrine, fenpropathrine, fenvalerate, flucitrinate, flumethrine, fluvalinate (D isomer), imiprothrine, cyhalothrine, λ-cyhalothrine, permethrine, phenothrine, prallethrine, pyrethrine (natural product), resmethrine, tetramethrine, transfluthrine, θ-cypermethrine, silafluofen, t-fluvalinate, tefluthrine, tralomethrine, ζ-cypermethrine.

[0126] Arthropod growth regulators: a) Chitin synthesis inhibitors: Benzoylureas: Chlorfluazurone, diflubenzuron, fluazurone, flucycloxurone, flufenoxurone, hexaflumurone, lufenuron, novaron, teflubenzuron, triflumuron, buprofezin, diofenolan, hexythiazox, etoxazole, chlorfentadine; b) Ecdysone antagonists: Halofenozide, methoxyfenozide, tebufenozide; c) Juvenoids: Pyriproxyfen, methoprene (including S-methoprene), phenoxycarb; d) Lipid biosynthesis inhibitors: Spirodiclofen.

[0127] Other antiparasitic drugs: acekinosyl, amitraz, AKD-1022, ANS-118, azadirachtin, Bacillus thuringiensis thuringiensis), bensaltap, bifenazate, binapacril, bromopropylate, BTG-504, BTG-505, campechlor, cartap, chlorobenzylate, chlordimeform, chlorfenapyr, chromafenozide, clothianidine, siromazine, diaclodene, diafenthiurone, DBI-3204, dinactin, dihydroxymethyldihydroxypyrrolidine, dinovtone, dinocap, endosulfan, ethiprole, etofenprox, phenazaquin, flumite, MTI-800, fenpyroximate, fluacrypyrim, flubendimine, flubrositrinate, flufenzin, flufenprox, fluproxyfen, halofenprox ofenprox), hydramethylnon, IKI-220, Kanemite, NC-196, Neem Guard, Nidinorterfuran, Nitenpyram, SD-35651, WL-108477, Pyridaryl, Propargit, Protrifenbut, Pymethrozine, Pyridaben, Pyrimidifen, NC-1111, R-195, RH-0345, RH-2485, RYI-210, S-1283, S-1833, SI-8601, Silafluofen, Cyromazine, Spinosad, Tebufenpyrad, Tetradiphon, Tetranactin, Thiacloprid, Thiocyclam, Thiamethoxam, Tolfenpyrad, Triazamate, Triethoxyspinosine, Trinactin, Berbutin, Bertarek, YI-5301.

[0128] Biological agents: Bacillus thuringiensis ssp aizawai, kurstaki, Bacillus thuringiensis δ-endotoxin, baculovirus, entomopathogenic bacteria, viruses, and fungi.

[0129] Fungicides: Chlortetracycline, oxytetracycline, streptomycin.

[0130] Other biological agents: Enrofloxacin, Febantel, Penetamate, Moroxicam, Cephalexin, Kanamycin, Pimobendan, Clenbuterol, Omeprazole, Thiamrin, Benazepril, Pyriprole, Cefquinom, Florfenicol, Buserelin, Cefobesin, Tulathromycin, Cefthiol, Carprofen, Metaflumizone, Praziqualantel, Tricrabendazole.

[0131] Another aspect of the present invention relates to the use of a compound of formula (I) or a preferred individual compound as defined above, a composition comprising at least one compound of formula (I) or at least one preferred individual compound as defined above, or a bactericidal, fungicidal or insecticidal mixture comprising at least one compound of formula (I) or at least one preferred individual compound as defined above, in admixtures with the other bactericidal, fungicidal or insecticidal agents, for the purpose of controlling or preventing extrinsing of non-biological materials by plants such as useful plants, such as crop plants, such as their reproductive bodies such as seeds, or harvested crops such as harvested food crops, or by plant pathogenic microorganisms such as insects or preferably fungi.

[0132] Further aspects of the present invention relate to a method for controlling or preventing extrinsing of non-biological materials by plants such as useful plants, such as crop plants, their reproductive bodies such as seeds, or harvested crops such as harvested food crops, or by plant pathogenic or potentially harmful putrefactive microorganisms or organisms such as insects or especially fungi, the method comprising the step of applying a compound of formula (I) or any of the preferred individual compounds defined above as an active ingredient to any part of a plant, a part of a plant or its habitat, its reproductive body, or non-biological material.

[0133] Control or prevention means reducing extrinsic parasitism by plant pathogenic or potentially harmful putrefactive microorganisms or organisms, such as insects or especially fungi, to a level that demonstrates improvement.

[0134] A preferred method for controlling or preventing ectoparasitism of crop plants by plant pathogenic microorganisms, particularly fungi, or insects, and which involves the application of a compound of formula (I) or an agricultural chemical composition containing at least one of the said compounds, is foliar application. The frequency and amount of application will depend on the risk of ectoparasitism by the corresponding pathogen or insect. However, the compound of formula (I) can also be introduced into the plant from the roots through the soil (osmotic translocation) by drenching the plant habitat with a liquid formulation or by applying the compound to the soil in solid form, such as granular form (soil application). In the case of rice crops, such granular material can be applied to flooded paddy fields. The compound of formula (I) can be applied to seeds (coated) by impregnating the seeds or tubers with a liquid formulation of a fungicide or by coating them with a solid formulation.

[0135] For example, formulations such as compositions containing a compound of formula (I) and, if necessary, a solid or liquid additive or monomer to encapsulate the compound of formula (I) can be prepared in known ways, typically by homogeneously mixing and / or grinding the compound together with an extender such as a solvent, a solid carrier, and optionally a surface-active compound (surfactant).

[0136] The advantageous dosage is typically 5 g to 2 kg of the active ingredient (ai) per hectare (ha), preferably 10 g to 1 kg ai / ha, and most preferably 20 g to 600 g ai / ha. When used as a seed drenching agent, a convenient dosage is 10 mg to 1 g of the active substance per 1 kg of seeds.

[0137] When the combination of the present invention is used for seed treatment, an amount of 0.001 to 50 g of the compound of formula (I) per 1 kg of seeds, preferably 0.01 to 10 g per 1 kg of seeds, is generally considered sufficient.

[0138] The compositions of the present invention may be any of the conventional forms, for example, a two-component system, a dry seed treatment powder (DS), a seed treatment emulsion (ES), a seed treatment fluid 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 suspension emulsion (SE), a capsule suspension (CS), water-dispersible granules (WG), or emulsifying granules. It may be employed in the form of any technically preferred formulation, such as granules (EG), emulsions, water-in-oil (EO), emulsions, oil-in-water (EW), microemulsions (ME), oil dispersions (OD), oil-miscible fluids (OF), oil-miscible liquids (OL), soluble concentrates (SL), ultra-low volume suspensions (SU), ultra-low volume liquids (UL), industrial concentrates (TK), dispersible concentrates (DC), wettable powders (WP), or in combination with agriculturally acceptable auxiliaries.

[0139] Such compositions can be produced in a conventional manner, for example, by mixing an active ingredient with a suitable inert formulation (diluent, solvent, filler, and optionally other components such as surfactants, biocides, antifreezes, spreading agents, thickeners, and compounds that provide adjuvant activity). Conventional slow-release formulations can also be used when a sustained effect over a long period is desired. In particular, formulations applied in spray form, such as water-dispersible concentrates (e.g., EC, SC, DC, OD, SE, EW, EO, etc.), wettable powders, and granules, may contain surfactants such as wetting agents, dispersants, and other compounds that provide adjuvant effects, such as formaldehyde-naphthalene sulfonate condensates, alkylaryl sulfonates, lignin sulfonates, fatty alkyl sulfates, and ethoxylated alkylphenols and ethoxylated aliphatic alcohols.

[0140] The seed coating formulation is applied to seeds in a manner known in itself, utilizing the combination and diluent of the present invention in a preferred seed coating formulation form, such as an aqueous suspension or a dry powder form having good adhesion to seeds. Such seed coating formulations are known in the art. The seed coating formulation may contain a single active ingredient or a combination of active ingredients in encapsulated form, for example, as a slow-release capsule or microcapsule.

[0141] Typically, a formulation comprises 0.01 to 90% by weight of an active agent, 0 to 20% of an agriculturally acceptable surfactant, and 10 to 99.99% of solid or liquid inert formulations and auxiliary agents, wherein the active agent consists of at least a compound of formula (I), along with components (B) and (C), and optionally other active agents, particularly bactericides or preservatives. The concentrated form of the composition generally contains about 2 to 80%, preferably about 5 to 70% by weight of the active agent. The application form of the formulation may contain, for example, 0.01 to 20% by weight, preferably 0.01 to 5% by weight of the active agent. While commercially available products may preferably be formulated as concentrates, end users typically utilize diluted formulations.

[0142] Table 1 below illustrates examples of individual compounds of formula (I) according to the present invention.

[0143] Table A-1 shows formula (Ib) [ka] We provide 48 compounds A-1.001 to A-1.048, where A is N and R 7 is hydrogen, R 1 is tetrahydrofuran-3-yl, and R 2 is hydrogen, R 4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0144] [Table 1-1] [Table 1-2]

[0145] Table A-2 provides 48 compounds of formula (Ib), A-2.001 to A-2.048, where A is N and R 7 is hydrogen, R 1 is tetrahydrofuran-3-yl, and R 2 is fluoro, and R 4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0146] Table A-3 provides 48 compounds of formula (Ib), A-3.001 to A-3.048, where A is N and R 7 is hydrogen, R 1 is tetrahydrofuran-2-yl, and R 2 is hydrogen, R 4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0147] Table A-4 provides 48 compounds of formula (Ib), A-4.001 to A-4.048, where A is N and R 7 is hydrogen, R 1 is tetrahydrofuran-2-yl, and R 2 is fluoro, and R 4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0148] Table A-5 provides 48 compounds of formula (Ib), A-5.001 to A-5.048, where A is N and R 7 is hydrogen, R 1 It is oxetane-3-yl, and R 2 is hydrogen, R 4 , R5 , R 6 and R 8 This is defined in Table 1.

[0149] Table A-6 provides 48 compounds of formula (Ib), A-6.001 to A-6.048, where A is N and R 7 is hydrogen, R 1 It is oxetane-3-yl, and R 2 is fluoro, and R 4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0150] Table A-7 provides 48 compounds of formula (Ib), A-7.001 to A-7.048, where A is N and R 7 is hydrogen, R 1 It is 1-methylsulfonylethyl, and R 2 is hydrogen, R 4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0151] Table A-8 provides 48 compounds of formula (Ib), A-8.001 to A-8.048, where A is N and R 7 is hydrogen, R 1 It is 1-methylsulfonylethyl, and R 2 is fluoro, and R 4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0152] Table A-9 provides 48 compounds of formula (Ib), A-9.001 to A-9.048, where A is N and R 7 is hydrogen, R 1 1-methylsulfinylethyl, R 2 is hydrogen, R 4 , R 5 , R6 and R 8 This is defined in Table 1.

[0153] Table A-10 provides 48 compounds of formula (Ib), A-10.001 to A-10.048, where A is N and R 7 is hydrogen, R 1 1-methylsulfinylethyl, R 2 is fluoro, and R 4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0154] Table A-11 provides 48 compounds of formula (Ib), A-11.001 to A-11.048, where A is N and R 7 is hydrogen, R 1 1-methylsulfanylethyl, R 2 is hydrogen, R 4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0155] Table A-12 provides 48 compounds of formula (Ib), A-12.001 to A-12.048, where A is N and R 7 is hydrogen, R 1 1-methylsulfanylethyl, R 2 is fluoro, and R 4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0156] Table A-13 provides 48 compounds of formula (Ib), A-13.001 to A-13.048, where A is N and R 7 is hydrogen, R 1 is 1-methoxyethyl, and R 2 is hydrogen, R 4 , R 5 , R 6and R 8 This is defined in Table 1.

[0157] Table A-14 provides 48 compounds of formula (Ib), A-14.001 to A-14.048, where A is N and R 7 is hydrogen, R 1 is 1-methoxyethyl, and R 2 is fluoro, and R 4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0158] Table A-15 provides 48 compounds of formula (Ib), A-15.001 to A-15.048, where A is N and R 7 is hydrogen, R 1 is 1-isopropoxyethyl, and R 2 is hydrogen, R 4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0159] Table A-16 provides 48 compounds of formula (Ib), A-16.001 to A-16.048, where A is N and R 7 is hydrogen, R 1 is 1-isopropoxyethyl, and R 2 is fluoro, and R 4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0160] Table A-17 provides 48 compounds of formula (Ib), A-17.001 to A-17.048, where A is N and R 7 is hydrogen, R 1 It is 1-tert-butoxyethyl, and R 2 is hydrogen, R 4 , R 5 , R 6 and R 8This is defined in Table 1.

[0161] Table A-18 provides 48 compounds of formula (Ib), A-18.001 to A-18.048, where A is N and R 7 is hydrogen, R 1 It is 1-tert-butoxyethyl, and R 2 is fluoro, and R 4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0162] Table A-19 provides 48 compounds of formula (Ib), A-19.001 to A-19.048, where A is N and R 7 is hydrogen, R 1 is isopropoxymethyl, and R 2 is hydrogen, R 4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0163] Table A-20 provides 48 compounds of formula (Ib), A-20.001 to A-20.048, where A is N and R 7 is hydrogen, R 1 is isopropoxymethyl, and R 2 is fluoro, and R 4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0164] Table A-21 provides 48 compounds of formula (Ib), A-21.001 to A-21.048, where A is N and R 7 is hydrogen, R 1 It is tert-butoxymethyl, and R 2 is hydrogen, R 4 , R 5 , R 6 and R 8This is defined in Table 1.

[0165] Table A-22 provides 48 compounds of formula (Ib), A-22.001 to A-22.048, where A is N and R 7 is hydrogen, R 1 It is tert-butoxymethyl, and R 2 is fluoro, and R 4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0166] Table A-23 provides 48 compounds of formula (Ib), A-23.001 to A-23.048, where A is N and R 7 is -C(O)2CH3, and R 1 is tetrahydrofuran-3-yl, and R 2 is hydrogen, R 4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0167] Table A-24 provides 48 compounds of formula (Ib), A-24.001 to A-24.048, where A is N and R 7 is -C(O)2CH3, and R 1 is tetrahydrofuran-3-yl, and R 2 is fluoro, and R 4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0168] Table A-25 provides 48 compounds of formula (Ib), A-25.001 to A-25.048, where A is N and R 7 is -C(O)2CH3, and R 1 is tetrahydrofuran-2-yl, and R 2 is hydrogen, R 4 , R 5 , R 6and R 8 This is defined in Table 1.

[0169] Table A-26 provides 48 compounds of formula (Ib), A-26.001 to A-26.048, where A is N and R 7 is -C(O)2CH3, and R 1 is tetrahydrofuran-2-yl, and R 2 is fluoro, and R 4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0170] Table A-27 provides 48 compounds of formula (Ib), A-27.001 to A-27.048, where A is N and R 7 is -C(O)2CH3, and R 1 It is oxetane-3-yl, and R 2 is hydrogen, R 4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0171] Table A-28 provides 48 compounds of formula (Ib), A-28.001 to A-28.048, where A is N and R 7 is -C(O)2CH3, and R 1 It is oxetane-3-yl, and R 2 is fluoro, and R 4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0172] Table A-29 provides 48 compounds of formula (Ib), A-29.001 to A-29.048, where A is N and R 7 is -C(O)2CH3, and R 1 It is 1-methylsulfonylethyl, and R 2 is hydrogen, R 4 , R 5, R 6 and R 8 This is defined in Table 1.

[0173] Table A-30 provides 48 compounds of formula (Ib), A-30.001 to A-30.048, where A is N and R 7 is -C(O)2CH3, and R 1 It is 1-methylsulfonylethyl, and R 2 is fluoro, and R 4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0174] Table A-31 provides 48 compounds of formula (Ib), A-31.001 to A-31.048, where A is N and R 7 is -C(O)2CH3, and R 1 1-methylsulfinylethyl, R 2 is hydrogen, R 4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0175] Table A-32 provides 48 compounds of formula (Ib), A-32.001 to A-32.048, where A is N and R 7 is -C(O)2CH3, and R 1 1-methylsulfinylethyl, R 2 is fluoro, and R 4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0176] Table A-33 provides 48 compounds of formula (Ib), A-33.001 to A-33.048, where A is N and R 7 is -C(O)2CH3, and R 1 1-methylsulfanylethyl, R 2 is hydrogen, R4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0177] Table A-34 provides 48 compounds of formula (Ib), A-34.001 to A-34.048, where A is N and R 7 is -C(O)2CH3, and R 1 1-methylsulfanylethyl, R 2 is fluoro, and R 4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0178] Table A-35 provides 48 compounds of formula (Ib), A-35.001 to A-35.048, where A is N and R 7 is -C(O)2CH3, and R 1 is 1-methoxyethyl, and R 2 is hydrogen, R 4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0179] Table A-36 provides 48 compounds of formula (Ib), A-36.001 to A-36.048, where A is N and R 7 is -C(O)2CH3, and R 1 is 1-methoxyethyl, and R 2 is fluoro, and R 4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0180] Table A-37 provides 48 compounds of formula (Ib), A-37.001 to A-37.048, where A is N and R 7 is -C(O)2CH3, and R 1 is 1-isopropoxyethyl, and R 2is hydrogen, R 4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0181] Table A-38 provides 48 compounds of formula (Ib), A-38.001 to A-38.048, where A is N and R 7 is -C(O)2CH3, and R 1 is 1-isopropoxyethyl, and R 2 is fluoro, and R 4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0182] Table A-39 provides 48 compounds of formula (Ib), A-39.001 to A-39.048, where A is N and R 7 is -C(O)2CH3, and R 1 It is 1-tert-butoxyethyl, and R 2 is hydrogen, R 4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0183] Table A-40 provides 48 compounds of formula (Ib), A-40.001 to A-40.048, where A is N and R 7 is -C(O)2CH3, and R 1 It is 1-tert-butoxyethyl, and R 2 is fluoro, and R 4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0184] Table A-41 provides 48 compounds of formula (Ib), A-41.001 to A-41.048, where A is N and R 7 is -C(O)2CH3, and R 1is isopropoxymethyl, and R 2 is hydrogen, R 4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0185] Table A-42 provides 48 compounds of formula (Ib), A-42.001 to A-42.048, where A is N and R 7 is -C(O)2CH3, and R 1 is isopropoxymethyl, and R 2 is fluoro, and R 4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0186] Table A-43 provides 48 compounds of formula (Ib), A-43.001 to A-43.048, where A is N and R 7 is -C(O)2CH3, and R 1 It is tert-butoxymethyl, and R 2 is hydrogen, R 4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0187] Table A-44 provides 48 compounds of formula (Ib), A-44.001 to A-44.048, where A is N and R 7 is -C(O)2CH3, and R 1 It is tert-butoxymethyl, and R 2 is fluoro, and R 4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0188] Table A-45 provides 48 compounds of formula (Ib), A-45.001 to A-45.048, where A is N and R 7is -C(O)2CH2CH3, and R 1 is tetrahydrofuran-3-yl, and R 2 is hydrogen, R 4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0189] Table A-46 provides 48 compounds of formula (Ib), A-46.001 to A-46.048, where A is N and R 7 is -C(O)2CH2CH3, and R 1 is tetrahydrofuran-3-yl, and R 2 is fluoro, and R 4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0190] Table A-47 provides 48 compounds of formula (Ib), A-47.001 to A-47.048, where A is N and R 7 is -C(O)2CH2CH3, and R 1 is tetrahydrofuran-2-yl, and R 2 is hydrogen, R 4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0191] Table A-48 provides 48 compounds of formula (Ib), A-48.001 to A-48.048, where A is N and R 7 is -C(O)2CH2CH3, and R 1 is tetrahydrofuran-2-yl, and R 2 is fluoro, and R 4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0192] Table A-49 provides 48 compounds of formula (Ib), A-49.001 to A-49.048, where A is N and R 7 is -C(O)2CH2CH3, and R 1 It is oxetane-3-yl, and R 2 is hydrogen, R 4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0193] Table A-50 provides 48 compounds of formula (Ib), A-50.001 to A-50.048, where A is N and R 7 is -C(O)2CH2CH3, and R 1 It is oxetane-3-yl, and R 2 is fluoro, and R 4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0194] Table A-51 provides 48 compounds of formula (Ib), A-51.001 to A-51.048, where A is N and R 7 is -C(O)2CH2CH3, and R 1 It is 1-methylsulfonylethyl, and R 2 is hydrogen, R 4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0195] Table A-52 provides 48 compounds of formula (Ib), A-52.001 to A-52.048, where A is N and R 7 is -C(O)2CH2CH3, and R 1 It is 1-methylsulfonylethyl, and R 2 is fluoro, and R 4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0196] Table A-53 provides 48 compounds of formula (Ib), A-53.001 to A-53.048, where A is N and R 7 is -C(O)2CH2CH3, and R 1 1-methylsulfinylethyl, R 2 is hydrogen, R 4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0197] Table A-54 provides 48 compounds of formula (Ib), A-54.001 to A-54.048, where A is N and R 7 is -C(O)2CH2CH3, and R 1 1-methylsulfinylethyl, R 2 is fluoro, and R 4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0198] Table A-55 provides 48 compounds of formula (Ib), A-55.001 to A-55.048, where A is N and R 7 is -C(O)2CH2CH3, and R 1 1-methylsulfanylethyl, R 2 is hydrogen, R 4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0199] Table A-56 provides 48 compounds of formula (Ib), A-56.001 to A-56.048, where A is N and R 7 is -C(O)2CH2CH3, and R 1 1-methylsulfanylethyl, R 2 is fluoro, and R 4 , R 5 , R 6 and R 8This is defined in Table 1.

[0200] Table A-57 provides 48 compounds of formula (Ib), A-57.001 to A-57.048, where A is N and R 7 is -C(O)2CH2CH3, and R 1 is 1-methoxyethyl, and R 2 is hydrogen, R 4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0201] Table A-58 provides 48 compounds of formula (Ib), A-58.001 to A-58.048, where A is N and R 7 is -C(O)2CH2CH3, and R 1 is 1-methoxyethyl, and R 2 is fluoro, and R 4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0202] Table A-59 provides 48 compounds of formula (Ib), A-59.001 to A-59.048, where A is N and R 7 is -C(O)2CH2CH3, and R 1 is 1-isopropoxyethyl, and R 2 is hydrogen, R 4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0203] Table A-60 provides 48 compounds of formula (Ib), A-60.001 to A-60.048, where A is N and R 7 is -C(O)2CH2CH3, and R 1 is 1-isopropoxyethyl, and R 2 is fluoro, and R 4 , R 5 , R6 and R 8 This is defined in Table 1.

[0204] Table A-61 provides 48 compounds of formula (Ib), A-61.001 to A-61.048, where A is N and R 7 is -C(O)2CH2CH3, and R 1 It is 1-tert-butoxyethyl, and R 2 is hydrogen, R 4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0205] Table A-62 provides 48 compounds of formula (Ib), A-62.001 to A-62.048, where A is N and R 7 is -C(O)2CH2CH3, and R 1 It is 1-tert-butoxyethyl, and R 2 is fluoro, and R 4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0206] Table A-63 provides 48 compounds of formula (Ib), A-63.001 to A-63.048, where A is N and R 7 is -C(O)2CH2CH3, and R 1 is isopropoxymethyl, and R 2 is hydrogen, R 4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0207] Table A-64 provides 48 compounds of formula (Ib), A-64.001 to A-64.048, where A is N and R 7 is -C(O)2CH2CH3, and R 1 is isopropoxymethyl, and R 2 is fluoro, and R4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0208] Table A-65 provides 48 compounds of formula (Ib), A-65.001 to A-65.048, where A is N and R 7 is -C(O)2CH2CH3, and R 1 It is tert-butoxymethyl, and R 2 is hydrogen, R 4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0209] Table A-66 provides 48 compounds of formula (Ib), A-66.001 to A-66.048, where A is N and R 7 is -C(O)2CH2CH3, and R 1 It is tert-butoxymethyl, and R 2 is fluoro, and R 4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0210] Table A-67 provides 12 compounds of formula (Ib), A-67.001 to A-66.012, where A is N and R 7 is hydrogen, R 1 It is tetrahydropyran-4-yl, and R 2 is hydrogen, R 4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0211] Table A-68 provides 12 compounds A-68.001 to A-68.012 of formula (Ib), where A is N and R 7 is hydrogen, R 1 It is tetrahydropyran-4-yl, and R 2is fluoro, and R 4 , R 5 , R 6 and R 8 This is defined in Table 1.

[0212] Formulation example

[0213] [Table 2]

[0214] A wettable powder can be obtained by thoroughly mixing the active ingredient with an auxiliary agent and grinding the mixture thoroughly in a suitable mill. This can then be diluted with water to obtain a suspension of the desired concentration.

[0215] [Table 3]

[0216] By thoroughly mixing the active ingredient with an auxiliary agent and then grinding the mixture thoroughly in a suitable mill, a powder can be obtained that can be used directly for seed treatment.

[0217] emulsifiable concentrate Active ingredient [compound of formula (I)] 10% Octylphenol polyethylene glycol ether 3% (4-5 mol of ethylene oxide) Calcium dodecylbenzenesulfonate 3% Castor oil polyglycol ether (35 mol ethylene oxide) 4% Cyclohexanone 30% Xylene mixture 50%

[0218] Any emulsion of the required dilution ratio that can be used for plant protection can be obtained from this concentrate by dilution with water.

[0219] [Table 4]

[0220] A ready-to-use powder is obtained by mixing the active ingredient with a carrier and grinding the mixture in a suitable mill. Such powders can also be used for drying and coating seeds.

[0221] Extruded granules Active ingredient [compound of formula (I)] 15% Sodium lignosulfonate 2% Carboxymethylcellulose 1% Kaolin 82%

[0222] The active ingredients are mixed and ground together with an auxiliary agent, and this mixture is humidified with water. The mixture is then extruded and dried in an airflow.

[0223] Coated granules Active ingredient [compound of formula (I)] 8% Polyethylene glycol (mol. wt. 200) 3% Kaolin 89%

[0224] Finely ground active ingredients are uniformly applied to kaolin humidified with polyethylene glycol in a mixer. This yields coated granules that do not generate dust.

[0225] Suspension concentrate Active ingredient [compound of formula (I)] 40% Propylene glycol 0% Nonylphenol polyethylene glycol ether (15 mol ethylene oxide) 6% Sodium lignosulfonate 10% Carboxymethylcellulose 1% Silicone oil (in the form of a 75% emulsion in water) 1% water 32%

[0226] Finely ground active ingredients are completely mixed with auxiliary agents to obtain a suspension concentrate, from which suspensions of any desired dilution ratio can be obtained by dilution with water. Such dilutions allow living plants and plant propagation materials to be treated by spraying, pouring, or immersion to protect them from microbial ectoplasty.

[0227] Concentrated flowable formulation for seed treatment Active ingredient [compound of formula (I)] 40% Propylene glycol 5% Copolymer Butanol PO / EO 2% Tristyrenephenol + 10-20 molar EO 2% 1,2-Benzisothiazolin-3-one (in the form of a 20% aqueous solution) 0.5% Monoazo pigment calcium salt 5% Silicone oil (in the form of a 75% emulsion in water) 0.2% Water 45.3%

[0228] Finely ground active ingredients are completely mixed with auxiliary agents to obtain a suspension concentrate, from which suspensions of any desired dilution ratio can be obtained by dilution with water. Such dilutions allow living plants and plant propagation materials to be treated by spraying, pouring, or immersion to protect them from microbial ectoplasty.

[0229] Slow-release capsule suspension Mix 28 parts of the compound of formula (I) with 2 parts of an aromatic solvent and 7 parts of a toluene diisocyanate / polymethylene-polyphenyl isocyanate mixture (8:1). Emulsify this mixture in a mixture of 1.2 parts of polyvinyl alcohol, 0.05 parts of a defoaming agent, and 51.6 parts of water until the desired particle size is achieved. Add 2.8 parts of 1,6-diaminohexane in 5.3 parts of water to this emulsion. Stir the mixture until the polymerization reaction is complete.

[0230] The resulting capsule suspension is stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersant. This capsule suspension formulation contains 28% of the active ingredient. The intermediate capsule diameter is 8 to 15 microns.

[0231] In an apparatus suitable for this purpose, the obtained formulation is applied to seeds as an aqueous suspension. [Examples]

[0232] The following examples illustrate the present invention. The compounds of the present invention can be distinguished from known compounds by their higher potency at low doses, which can be verified by those skilled in the art using the experimental methods outlined in the examples and, if necessary, by using even lower doses such as 50 ppm, 12.5 ppm, 6 ppm, 3 ppm, 1.5 ppm, 0.8 ppm, or 0.2 ppm.

[0233] Compounds of formula (I) may have many advantages, particularly those related to their use as a pesticide active ingredient with a favorable level of biological activity or pesticide activity for protecting plants from fungal diseases (e.g., high biological activity, a favorable range of activity, a high safety profile (including improved crop tolerance), improved physicochemical properties, or high biodegradability).

[0234] List of Abbreviations °C = degrees Celsius, CDCl3 = chloroform-d, d = doublet, DCM = dichloromethane, DMF = dimethylformamide, HATU = 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate, m = multiplet, MHz = megahertz, N = normal, RT = room temperature, s = singlet.

[0235] overview Throughout this specification, temperature is expressed in degrees Celsius (°C), and "mp" means melting point. LC / MS means liquid chromatography-mass spectroscopy, and the apparatus and method are described below.

[0236] Method A: Waters ACQUITY UPLC, Waters UPLC HSS T3, particle size 1.8 mm, 30 × 2.1 mm column, 0.85 mL / min, 60°C, H2O / MeOH 95:5 + 0.05% HCOOH (90%) / CH3CN + 0.05% HCOOH (10%) - 1.2 min - CH3CN + 0.05% HCOOH (100%) - 0.30 min, Waters ACQUITY SQD mass spectrometer, ionization method: electrospray (ESI), polarity: cation, capillary (kV) 3.00, cone (V) 30.00, extractor (V) 2.00, source temperature (°C) 150, desolvation temperature (°C) 350, cone gas flow (L / Hr) 0, desolvation gas flow (L / Hr) 650).

[0237] Method B: Waters ACQUITY UPLC, Waters UPLC HSS T3, particle size 1.8 mm, 30 × 2.1 mm column, 0.85 mL / min, 60°C, H2O / MeOH 95:5 + 0.05% HCOOH (90%) / CH3CN + 0.05% HCOOH (10%) - 2.7 min - CH3CN + 0.05% HCOOH (100%) - 0.30 min, Waters ACQUITY SQD mass spectrometer, ionization method: electrospray (ESI), polarity: cation, capillary (kV) 3.00, cone (V) 30.00, extractor (V) 2.00, source temperature (°C) 150, desolvation temperature (°C) 350, cone gas flow (L / Hr) 0, desolvation gas flow (L / Hr) 650).

[0238] Method C: A Waters Corporation ACQUITY mass spectrometer (SQD or SQDII single quadrupole mass spectrometer) equipped with an electrospray source (polarity: cation or anion, capillary: 3.0kV, cone: 30V, extractor: 3.00V, source temperature: 150℃, desolventing temperature: 400℃, cone gas flow: 60L / hr, desolventing gas flow: 700L / hr, mass range: 140~800Da), and a Waters Corporation ACQUITY UPLC equipped with a solvent degasser, binary pump, heated column compartment, and diode array detector. Column: Waters UPLC HSS T3, 1.8 μm, 30 × 2.1 mm, Temperature: 60°C, DAD wavelength range (nm): 210~400, Solvent gradient: A = Water / Methanol 9:1 + 0.1% Formic Acid, B = Acetonitrile + 0.1% Formic Acid, Gradient: 0~100% B over 2.5 minutes; Flow rate (ml / min) 0.75).

[0239] Example 1: Preparation of 2-[(2,6-difluoro-4-pyridyl)-(tetrahydrofuran-3-carbonyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (Example P-2, Table 2) and 2-[(2,6-difluoro-4-pyridyl)-(tetrahydrofuran-3-carbonyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-N-(tetrahydrofuran-3-carbonyl)thiazole-4-carboxamide (Example P-1, Table 2) [ka] (Compound P-3, Table 2), and [ka] (Compound P-1, Table 2) A solution of tetrahydrofuran-3-carboxylic acid (0.174 g, 0.143 mL, 1.48 mmol) in DCM (9 mL) was treated with one drop of DMF, followed by oxalyl chloride (0.192 g, 0.13 mL, 1.48 mmol) under argon. The mixture was stirred under argon at room temperature for 30 minutes to obtain tetrahydrofuran-3-carbonyl chloride. To this DCM solution, 2-[(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (0.350 g, 0.993 mmol, prepared as described in International Publication No. 2019 / 105933), followed by triethylamine (0.308 g, 0.42 mL, 2.98 mmol), was added under argon at room temperature. The resulting pale yellow solution was stirred at room temperature under argon for 2.5 hours, at which point LC-MS analysis indicated completion of the reaction. The reaction mixture was treated with Isolute® and concentrated under reduced pressure. Purification by flash chromatography with ethyl acetate / cyclohexane yielded a mixture of the two products, which was further purified by reverse-phase chromatography to obtain 2-[(2,6-difluoro-4-pyridyl)-(tetrahydrofuran-3-carbonyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (Example P-2, Table 2) as a white powder as the first eluted product. 1 H NMR (400MHz, CDCl3): δ ppm 0.94(s,3H)1.13(s,3H)1.49-1.59(m,2H)1.65-1.78(m,1H)1.95-2.15(m,1H)2.19-2.30(m,1H)2.30-2.40(m,1H)2.81(s,3H)2 .99-3.14(m,1H)3.80-3.88(m,1H)3.88-3.95(m,1H)3.95-4.06(m,2H)4.10-4.26(quartet,1H)6.89(s,2H)6.95-7.06(broad d,1H); LC-MS (Method A): 451 [M+H], Rt: 1.09 min.

[0240] Further elution yielded a second product, 2-[(2,6-difluoro-4-pyridyl)-(tetrahydrofuran-3-carbonyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-N-(tetrahydrofuran-3-carbonyl)thiazole-4-carboxamide (compound P-1, Table 2), as a white powder. 1 H NMR (400MHz, CDCl3): δ ppm 1.09(s,3H)1.18(s,3H)1.53-1.66(m,2H)1.77-1.91(m,1H)2.07-2.22(m,2H)2.23-2.34(m,1H)2.41-2.51+2.62-2.71 (2×m,2H)2.81(s,3H)3.10-3.26(m,1H)3.77-4.05(m,6H)4.14-4.31+4.37-4.43(2×m,3H)6.81-6.92(2×s,2H)7.20(br d,J=8.44Hz, 1H); LC-MS (Method A): 549 [M+H], Rt: 1.15 min.

[0241] Example 2: Preparation of 2-[(2,6-difluoro-4-pyridyl)-(oxetane-3-carbonyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (Example P-4, Table 2) [ka] (Example P-4, Table 2) A solution of 2-[(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (0.050 g, 1.0, 0.14 mmol, prepared as described in International Publication No. 2019 / 105933) in DMF (1.4 mL) was treated with oxetane-3-carboxylic acid (0.019 g, 1.2, 0.17 mmol), N,N-diisopropylethylamine (0.048 g, 0.064 mL, 0.37 mmol) and HATU (0.082 g, 0.21 mmol). The resulting light brown solution was stirred at room temperature for 4 hours. After this, the reaction mixture was quenched with saturated sodium bicarbonate aqueous solution and diluted with water. Next, it was extracted twice with ethyl acetate, the combined organic layer was washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to obtain a light brown oil. The crude product was purified by reverse-phase chromatography with acetonitrile / water elution to obtain the title compound as a beige powder. 1 H NMR (400MHz, CDCl3)δ ppm 0.97(s,3H)1.14(s,3H)1.50-1.65(m,2H)1.65-1.81(m,1H)2.19-2.34(m,1H)2.84(s,3H)3.8 6-4.01(m,1H)4.13-4.26(m,1H)4.51-4.65(m,2H)4.92-5.06(m,2H)6.82(s,2H)6.91-7.08(br s,1H); LC-MS (Method A): 437 [M+H], Rt: 1.05 min.

[0242] Example 3: Preparation of 2-[(2,6-difluoro-4-pyridyl)-(tetrahydropyran-4-carbonyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (Example P-11, Table 2) A solution of tetrahydro-2h-pyran-4-carboxylic acid (6.282 g, 46.82 mmol) in acetonitrile (86 mL) was treated with 1-propanephosphonic anhydride (99.32 g, 93.00 mL, 156.1 mmol) and N,N-diisopropylethylamine (40.75 g, 54.6 mL, 10.00 mL, 312.1 mmol), and 2-[(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (11 g, 1.000 mL, 31.21 mmol, prepared as described in International Publication No. 2019 / 105933) was added to obtain a brown solution. The reaction mixture was stirred under argon at 50°C for 16 hours. After the reaction was complete, the reaction mixture was cooled and slowly added to saturated sodium bicarbonate aqueous solution at 0°C. Next, the reaction mixture was extracted with ethyl acetate (x3), the combined organic extract was washed once with brine, dried on anhydrous Na2SO4, filtered, and concentrated under reduced pressure to obtain 15.88 g of a light brown powder. The title product was obtained as a white powder by flash chromatography eluting with ethyl acetate / cyclohexane. 1 H NMR (400MHz, CDCl3)δ ppm 0.93(s,3H)1.13(s,3H)1.50-1.76(m,5H)1.97-2.09(m,2H)2.25(dtd,J=10.90,8.08,8.08,2.72Hz,1H)2.60(tt,J=11.26,3. 81Hz, 1H)2.81(s,3H)3.29(tt,J=11.90,1.91Hz,2H)4.01(dt,J=11.63,2.18Hz,2H)4.18(q,J=8.60Hz,1H)6.89(s,2H)6.99(br d,J=9.08Hz, 1H) LC-MS (Method A): 465 [M+H], Rt: 1.11 min.

[0243] Table 2 below shows the individual compounds illustrated by formula (I) according to the present invention.

[0244] [Table 5-1] [Table 5-2] [Table 5-3]

[0245] Biological examples: Example B1: Alternaria solani / Tomato / Leaf blight (Summer blight) Tomato leaf fragments (cv. Baby) were placed on agar in a multi-well plate (24-well type), and the formulated test compound, diluted with water, was sprayed onto them. Two days after application, a suspension of fungal spores was seeded onto the leaf fragments. The seeded leaf fragments were incubated in a climate cabinet under 12 / 12 hours (light / dark) light conditions at 23°C / 21°C (day / night) and 80% (rh). The activity of the compound was evaluated as disease control compared to the untreated sample when an appropriate level of disease damage appeared on the untreated test leaf fragments (5-7 days after application). The following compounds, at 200 ppm, provided at least 80% control of Alternaria solani compared to an untreated control showing significant disease development under the same conditions: P-1, P-2, P-3, P-4, P-5, P-6, P-9, P-10, and P-11.

[0246] Example B2: Botryotinia fuckeliana (Botrytis cinerea) / Liquid culture (gray mold disease) Fungal conidia stored at cryogenic temperatures were directly mixed into a nutrient solution medium (Vogels liquid medium). A (DMSO) solution of the test compound was placed in a microtiter plate (96-well type), and then the nutrient solution medium containing fungal spores was added. The test plate was incubated at 24°C, and 3-4 days after application, the inhibition of growth was measured by photometric method. The following compounds, at 20 ppm, resulted in at least 80% control of Botryotinia fuckeliana compared to an untreated control that showed significant disease development under the same conditions: P-2 and P-4.

[0247] Example B3: Glomerella lagenarium (Colletotrichum lagenarium) / Liquid culture (Anthracnose) Fungal conidia stored at cryogenic temperatures were directly mixed into a nutrient solution medium (PDB potato glucose medium). After adding a (DMSO) solution of the test compound to a microtiter plate (96-well type), the nutrient solution medium containing fungal spores was added. The test plate was incubated at 24°C, and 3-4 days after application, the inhibition of growth was measured by photometric method. The following compounds, at 20 ppm, resulted in at least 80% control of Glomerella lagenarium compared to an untreated control that showed significant disease development under the same conditions: P-1, P-2, P-3, P-4, P-6, P-9, P-10, and P-11.

[0248] Example B4: Blumeria graminis f.sp. tritici (Powdery mildew fungus (Erysiphe graminis f.sp. tritici)) / Wheat / Leaf blot prevention (Powdery mildew in wheat) A portion of wheat leaves (cv. Kanzler) was placed on agar in a multi-well plate (24-well type), and the formulated test compound, diluted with water, was sprayed onto it. One day after application, powdery mildew-infected plants were sown onto the leaf portions by shaking them on the test plate. The sown leaf portions were incubated in a climate chamber at 20°C and 60% relative humidity under a light environment of 24 hours in darkness followed by 12 hours of light / 12 hours in darkness. The activity of the compound was evaluated as disease control compared to untreated leaves when an appropriate level of disease damage appeared on a portion of the untreated test leaves (6-8 days after application). The following compounds, at 200 ppm, provided at least 80% control of Blumeria graminis f.sp. tritici compared to an untreated control that showed significant disease development under the same conditions: P-1, P-2, P-3, P-4, P-5, P-6, P-7, P-8, P-9, P-10, and P-11.

[0249] Example B5: Wheat tartar (Phaeosphaeria nodorum) (Septoria nodorum) / Wheat / Leaf blot prevention (tartar disease) Wheat leaf fragments (cv. Kanzler) were placed on agar in a multi-well plate (24-well type), and the formulated test compound, diluted in water, was sprayed onto the leaf fragments. Two days after application, a suspension of fungal spores was seeded onto the leaf fragments. The seeded test leaf fragments were incubated in an artificial climate chamber at 20°C and 75% rh under a 12-hour light / 12-hour darkness light environment. When an appropriate level of disease appeared on the untreated test leaf fragments (5-7 days after application), the activity of the compound was evaluated as the control rate of disease compared to the untreated sample. The following compounds, at 200 ppm, provided at least 80% control of Phaeosphaeria nodorum, the wheat blight fungus, compared to an untreated control that showed significant disease development under the same conditions: P-2, P-3, and P-10.

[0250] Example B6: Monographella nivalis (Microdochium nivale), a fungus that causes red wheat mold (root rot in cereals) / liquid culture (root rot in cereals) Fungal conidia stored at cryogenic temperatures were directly mixed into a nutrient solution medium (PDB potato glucose medium). A (DMSO) solution of the test compound was placed in a microtiter plate (96-well type), and then the nutrient solution medium containing fungal spores was added. The test plate was incubated at 24°C, and after 4-5 days from application, the inhibition of growth was measured by photometric method. The following compounds, at 20 ppm, resulted in at least 80% control of Monographella nivalis compared to an untreated control that showed significant disease development under the same conditions: P-1, P-2, P-3, P-4, P-5, P-6, P-9, P-10, and P-11.

[0251] Example B7: Mycosphaerella arachidis (Cercospora arachidicola) / Liquid culture (Early spot disease) Fungal conidia stored at cryogenic temperatures were directly mixed into a nutrient solution medium (PDB potato glucose medium). After adding a (DMSO) solution of the test compound to a microtiter plate (96-well type), the nutrient solution medium containing fungal spores was added. The test plate was incubated at 24°C, and after 4-5 days from application, the inhibition of growth was measured by photometric method. The following compounds, at 20 ppm, resulted in at least 80% control of Mycosphaerella arachidis compared to an untreated control that showed significant disease development under the same conditions: P-1, P-2, and P-10.

[0252] Example B8: Phakopsora pachyrhizi / Soybean / Preventive (Soybean rust disease) Soybean leaf fragments were placed on agar water in a multi-well plate (24-well type), and the formulated test compound, diluted in water, was sprayed onto them. One day after application, spores were sown onto the leaf fragments by spraying a spore suspension onto the underside of the leaves. After a 24-36 hour incubation period in darkness at 20°C and 75% rh in an artificial climate chamber, the leaf fragments were kept at 20°C with 12 hours of light / day and 75% rh. The activity of the compound was evaluated as the disease control rate compared to the untreated sample when an appropriate level of disease appeared on the untreated test leaf fragments (12-14 days after application). The following compounds, at 200 ppm, resulted in at least 80% control of Phakopsora pachyrhizi compared to an untreated control showing significant disease development under the same conditions: P-2, P-3, P-4, P-6, and P-9.

[0253] Example B9: Puccinia recondita f.sp. tritici / Wheat / Leaf blot treatment (red rust disease) Wheat leaf fragments (cv. Kanzler) are placed on agar in a multi-well plate (24-well type). A fungal spore suspension is seeded onto the leaf fragments. The plates are stored in the dark at 19°C and 75% rh. The formulated test compound, diluted in water, is applied one day after seeding. The leaf fragments are incubated in an artificial climate chamber at 19°C and 75% rh under a 12-hour light / 12-hour darkness light environment. When an appropriate level of disease appears on the untreated test leaf fragments (6-8 days after application), the activity of the compound is evaluated as the disease control rate compared to the untreated leaf fragments. The following compounds, at 200 ppm, provided at least 80% control of Puccinia recondita f.sp. tritici compared to an untreated control that showed significant disease development under the same conditions: P-1, P-2, P-3, P-4, P-5, P-6, P-9, and P-11.

[0254] Example B10: Puccinia recondita f.sp. tritici / Wheat / Leaf blot prevention (red rust disease) Wheat leaf fragments (cv. Kanzler) are placed on agar in a multi-well plate (24-well type), and the formulated test compound, diluted in water, is sprayed onto them. One day after application, a fungal spore suspension is seeded onto the leaf fragments. The seeded leaf fragments are incubated in an artificial climate chamber at 19°C and 75% rh under a 12-hour light / 12-hour darkness light environment. The activity of the compound is evaluated as the disease control rate compared to the untreated leaf fragments when an appropriate level of disease appears on the untreated test leaf fragments (7-9 days after application). The following compounds, at 200 ppm, provided at least 80% control of Puccinia recondita f.sp. tritici compared to an untreated control that showed significant disease development under the same conditions: P-1, P-2, P-3, P-4, P-5, P-6, P-7, P-9, P-10, and P-11.

[0255] Example B11: Magnaporthe grisea (rice blast fungus (Pyricularia oryzae)) / rice / leaf blot prevention (rice blast disease) Rice leaf fragments (cv. Ballila) were placed on agar in a multi-well plate (24-well type), and the formulated test compound, diluted in water, was sprayed onto them. Two days after application, a fungal spore suspension was seeded onto the leaf fragments. The seeded leaf fragments were incubated in an artificial climate chamber at 22°C and 80% rh under 24 hours of darkness, followed by 12 hours of light / 12 hours of darkness. The activity of the compound was evaluated as the disease control rate compared to the untreated leaf fragments when an appropriate level of disease appeared on the untreated test leaf fragments (5-7 days after application). The following compounds, at 200 ppm, resulted in at least 80% control of Magnaporthe grisea compared to an untreated control showing significant disease development under the same conditions: P-1, P-2, P-3, P-4, P-5, P-6, P-7, P-8, P-9, and P-10.

[0256] Example B12: Pyrenophora teres / Barley / Leaf blot prevention (reticulosis) Barley leaf fragments (cv. Hasso) were placed on agar in a multi-well plate (24-well type), and the formulated test compound, diluted in water, was sprayed onto the leaf fragments. Two days after application, a fungal spore suspension was seeded onto the leaf fragments. The seeded leaf fragments were incubated in an artificial climate chamber at 20°C and 65% rh under a 12-hour light / 12-hour darkness light environment. The activity of the compounds was evaluated as disease control compared to the untreated leaf fragments when an appropriate level of disease appeared in the untreated test leaf fragments (5-7 days after application). The following compounds, at 200 ppm, resulted in at least 80% control of Pyrenophora teres compared to an untreated control showing significant disease development under the same conditions: P-1, P-2, P-3, P-4, P-5, P-6, P-9, P-10, and P-11.

[0257] Example B13: Sclerotinia sclerotiorum / Liquid culture (Sclerotinia rot) Mycelial fragments of newly grown liquid-cultured fungi were directly mixed into a nutrient solution medium (PDB potato glucose liquid medium). A (DMSO) solution of the test compound was placed in a microtiter plate (96-well type), and then the nutrient solution medium containing the fungal material was added. The test plate was incubated at 24°C, and 3-4 days after application, the inhibition of growth was measured by photometric method. The following compound, at 20 ppm, resulted in at least 80% control of Sclerotinia sclerotiorum compared to an untreated control that showed significant disease development under the same conditions: P-10.

[0258] Example B14: Wheat leaf blight fungus (Mycosphaerella graminicola) (Septoria tritici) / liquid culture (leaf blight) Fungal conidia stored at cryogenic temperatures were directly mixed into a nutrient solution medium (PDB potato glucose medium). After adding a (DMSO) solution of the test compound to a microtiter plate (96-well type), the nutrient solution medium containing fungal spores was added. The test plate was incubated at 24°C, and after 4-5 days from application, the inhibition of growth was measured by photometric method. The following compounds, at 20 ppm, resulted in at least 80% control of wheat leaf blight fungus (Mycosphaerella graminicola) compared to an untreated control that showed significant disease development under the same conditions: P-1, P-2, P-3, P-4, P-9, P-10, and P-11. Another aspect of the present invention may be as follows: [1] Equation (I): [ka] (In the formula, A is either CH or N; R 1 C 1 ~C 4 Alkoxy C 1 ~C 2 Alkyl, C 1 ~C 6 Alkylsulfanyl C 1 ~C 6 Alkyl, C 1 ~C 6 Alkylsulfinyl C 1 ~C 6 Alkyl, C 1 ~C 6 Alkylsulfonyl C 1 ~C 6 The alkyl or heterocyclyl, wherein the heterocyclyl portion is a four-membered, five-membered, or six-membered non-aromatic monocyclic ring containing one, two, or three heteroatoms individually selected from nitrogen, oxygen, and sulfur; R 2 is hydrogen or halogen; R 3 C 1 ~C 8 It is alkyl; R 4 、R 5 、R 6 Each of them independently consists of hydrogen or C 1 ~C 4 It is alkyl; R 7 is hydrogen, C 1 ~C 4 Alkyl, C 1 ~C 6 Alkoxycarbonyl C 1 ~C 4 Alkyl, C 1 ~C 6 Alkoxycarbonyl or C 1 ~C 6 It is an alkoxy; R 8 is hydrogen, C 1 ~C 6 Alkoxy C 1 ~C 6 Alkylcarbonyl, C 1 ~C 6 Alkylsulfanyl C 1 ~C 6 Alkylcarbonyl, C 1 ~C 6 Alkylsulfinyl C 1 ~C 6 Alkylcarbonyl, C 1 ~C 6 Alkylsulfonyl C 1 ~C 6 (An alkylcarbonyl or heterocyclylcarbonyl, wherein the heterocyclyl portion is a 4-membered, 5-membered, or 6-membered non-aromatic monocyclic ring containing 1, 2, or 3 heteroatoms individually selected from nitrogen, oxygen, and sulfur.) A compound of the same, or its salt or N-oxide. 〔2〕R 1 C 1 ~C 4 Alkoxy C 1 ~C 2 Alkyl, C 1 ~C 3 Alkylsulfanyl C 1 ~C 3 Alkyl, C 1 ~C 3 Alkylsulfinyl C 1 ~C 3 Alkyl, C 1 ~C 3 Alkylsulfonyl C 1 ~C 3 The compound according to [1], wherein the compound is alkyl or heterocyclyl, and the heterocyclyl portion is a four-membered, five-membered or six-membered non-aromatic monocyclic ring containing one or two heteroatoms individually selected from nitrogen and oxygen. 〔3〕R 1 C 3 ~C 4 Alkoxy C 1 ~C 2 Alkyl, C 1 ~C 3 Alkylsulfanyl C 1 ~C 3 Alkyl, C 1 ~C 3 Alkylsulfinyl C 1 ~C 3 Alkyl, C 1 ~C 3 Alkylsulfonyl C1 ~C 3 The compound according to [1] or [2], wherein the compound is alkyl or heterocyclyl, and the heterocyclyl portion is a four-membered, five-membered or six-membered non-aromatic monocyclic ring containing one or two heteroatoms individually selected from nitrogen and oxygen. 〔4〕R 1 The compound described in [1] or [2] above is isopropoxymethyl, tert-butoxymethyl, 1-methoxyethyl, 1-isopropoxyethyl, 1-tert-butoxyethyl, 1-methylsulfonylethyl, oxetan-3-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, or tetrahydropyran-4-yl. 〔5〕R 1 C 1 ~C 3 Alkylsulfanyl C 1 ~C 3 Alkyl, C 1 ~C 3 Alkylsulfinyl C 1 ~C 3 Alkyl, C 1 ~C 3 Alkylsulfonyl C 1 ~C 3 The compound according to any one of claims [1] to [3], wherein the compound is alkyl or heterocyclyl, and the heterocyclyl portion is a four-membered, five-membered, or six-membered non-aromatic monocyclic ring containing one or two heteroatoms individually selected from nitrogen and oxygen. 〔6〕R 1 The compound is one of the compounds described in any one of the above [1] to [3] or [5], which is 1-methylsulfonylethyl, oxetan-3-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, or tetrahydropyran-4-yl. 〔7〕R 2 The compound is one of the items [1] to [6] above, wherein the compound is hydrogen or fluoro. 〔8〕R 3 The compound is methyl, as described in any one of the above items [1] to [6]. 〔9〕R 4 The compound is hydrogen, as described in any one of the items [1] to [7] above. 〔10〕R 5 and R 6 The compound is one of the compounds described in any one of the above [1] to [9], wherein both are methyl.

[11] A is N, and is a compound according to any one of the items [1] to

[10] above.

[12] A pesticide composition comprising an amount effective for fungicidal and fungicidal purposes of the compound of formula (I) described in any one of the above items [1] to

[11] .

[13] The composition according to

[12] , further comprising at least one additional active ingredient and / or an agriculturally chemistry acceptable diluent or carrier.

[14] A method for controlling or preventing ectoparasitism of useful plants by plant pathogenic microorganisms, wherein a bactericidal and fungicidal amount of the compound of formula (I) described in any one of the above items [1] to

[11] or the composition described in the above item

[12] or

[13] is applied to the plant, a part thereof or its habitat.

[15] Use of a compound of formula (I) described in any one of the above items [1] to

[11] as a fungicide or fungicide.

Claims

1. Equation (I): 【Chemistry 1】 (In the formula, A is N; R 1 These are isopropoxymethyl, tert-butoxymethyl, 1-isopropoxyethyl, 1-tert-butoxyethyl, 1-methylsulfonylethyl, oxetan-3-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, or tetrahydropyran-4-yl; R 2 It is a halogen; R 3 C 1 ~C 3 It is alkyl; R 4 is hydrogen; R 5 and R 6 are both C 1 -C 4 alkyl; R 7 is hydrogen; R 8 (It is hydrogen.) A compound of the same, or its salt or N-oxide.

2. R 1 The compound according to claim 1, wherein is 1-methylsulfonylethyl, oxetan-3-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, or tetrahydropyran-4-yl.

3. R 2 The compound according to claim 1 or 2, wherein is fluoro.

4. R 3 The compound according to any one of claims 1 to 3, wherein is methyl.

5. R 5 and R 6 The compound according to any one of claims 1 to 4, wherein both are methyl.

6. 2-[(2,6-difluoro-4-pyridyl)-(tetrahydrofuran-2-carbonyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (P-2); 2-[(2,6-difluoro-4-pyridyl)-(tetrahydrofuran-3-carbonyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (P-3); 2-[(2,6-difluoro-4-pyridyl)-(oxetane-3-carbonyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (P-4); 2-[2-tert-butoxypropanoyl-(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (P-5); 2-[(2,6-difluoro-4-pyridyl)-(2-isopropoxypropanoyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (P-6); 2-[(2-tert-butoxyacetyl)-(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (P-7); 2-[(2,6-difluoro-4-pyridyl)-(2-isopropoxyacetyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (P-8); 2-[(2,6-difluoro-4-pyridyl)-(2-methylsulfonylpropanoyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide (P-10); and 2-[(2,6-difluoro-4-pyridyl)-(tetrahydropyran-4-carbonyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide (P-11) A compound according to claim 1, selected from the following.

7. A pesticide composition comprising a compound of formula (I) according to any one of claims 1 to 6 in an amount effective for sterilization and fungicidal purposes.

8. The pesticide composition according to claim 7, further comprising at least one additional active ingredient and / or an agriculturally chemistry-acceptable diluent or carrier.

9. A method for controlling or preventing ectoparasitism of useful plants by plant pathogenic microorganisms, wherein a bactericidal and fungicidal amount of the compound of formula (I) described in any one of claims 1 to 6 or the composition described in claim 7 or 8 is applied to the plant, a part thereof, or its habitat.

10. Use of a compound of formula (I) according to any one of claims 1 to 6 as a disinfectant or fungicide, excluding medical procedures on humans.

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