BR112020010780B1 - OXADIAZOLE COMPOUND OR ITS SALTS, FUNGICIDE FOR AGRICULTURE, METHOD FOR CONTROLLING PLANT DISEASES AND ITS USE - Google Patents

Abstract

The development of new agricultural/horticultural fungicides is desired due to disease damage that continues to be a major problem, the evolution of diseases resistant to existing chemicals, and other factors in agricultural production such as agriculture and horticulture. The present invention provides an agricultural/horticultural fungicide having as its active ingredient a compound represented by the general formula (I) [in the formula, R1 represents a (a2) (C1-C6) alkyl, etc., R2 represents a group (b1) a hydrogen atom, etc., R3 represents a group (c1) a hydrogen atom or a (c2) (C1-C6) alkyl, etc., R4 represents a (d2) (C1-C6) alkyl, etc., X1, X2, X3 and X4 represent a (e1) hydrogen atom, etc., Y represents an oxygen atom, etc.] or their salts, and a method for using the same.

Description

Technical field

[0001] The present invention relates to a fungicide for agrohorticulture containing, as active ingredient, an oxadiazole compound or its salts, and a method for using the same.

Background

[0002] Patent literatures 1, 2 and 3 describe that certain types of oxadiazole derivatives have fungicidal activity against plant disease-causing bacteria.

List of quotes

[0003] Patent literature

[0004] PATENT LITERATURE 1: JP-A-63-162680

[0005] PATENT LITERATURE 2: WO2015/185485 A

[0006] PATENT LITERATURE 3: WO2017/055473 A

Summary of the invention

[0007] Technical problem to be solved

[0008] In the production of agricultural and horticultural crops or the like, crop damage caused by diseases is still large, and due to factors such as the occurrence of diseases resistant to existing drugs, the development of new fungicides for agrohorticulture is desirable.

Solution to the problem

[0009] As a result of intensive research to develop new fungicides, the present inventors have found specific compounds having the structures of hemiaminal structures and salts thereof, neither described nor suggested in any of the above-mentioned literatures, to be useful as fungicides for agrohorticulture to achieve the present invention.

[0010] In particular, the present invention relates to the following:

[0011] [1] A compound represented by the general formula (I) or its salts,

[0012] where

[0013] R1 indicates

[0014] (a1) a hydrogen atom;

[0015] (a2) a (C1-C6) alkyl group;

[0016] (a3) a (C2-C6) alkenyl group;

[0017] (a4) a (C2-C6) alkynyl group;

[0018] (a5) a (C3-C6) cycloalkyl group;

[0019] (a6) a halo (C1-C6) alkyl;

[0020] (a7) a (C2-C6) alkenyl halo;

[0021] (a8) a halo (C2-C6) alkynyl; or

[0022] (a9) a (C3-C6) cycloalkyl halo.

[0023] R2 indicates

[0024] (b1) a hydrogen atom;

[0025] (b2) a (C1-C6) alkyl group;

[0026] (b3) a (C2-C6) alkenyl group;

[0027] (b4) a (C2-C6) alkynyl group;

[0028] (b5) a (C3-C6) cycloalkyl group;

[0029] (b6) a (C1-C6) alkyl halo;

[0030] (b7) a (C2-C6) alkenyl halo;

[0031] (b8) a halo (C2-C6) alkynyl; or

[0032] (b9) a (C3-C6) cycloalkyl halo.

[0033] R3 indicates

[0034] (c1) a hydrogen atom;

[0035] (c2) a (C1-C6) alkyl group;

[0036] (c3) a (C2-C6) alkenyl;

[0037] (c4) a (C2-C6) alkynyl group;

[0038] (c5) a (C3-C6) cycloalkyl group;

[0039] (c6) a (C1-C6) alkylcarbonyl group; or

[0040] (c7) a (C1-C6) alkoxycarbonyl group.

[0041] R4 indicates

[0042] (d1) a hydrogen atom;

[0043] (d2) a (C1-C6) alkyl group;

[0044] (d3) a (C2-C6) alkenyl group;

[0045] (d4) a (C2-C6) alkynyl group;

[0046] (d5) a (C3-C6) cycloalkyl group;

[0047] (d6) a (C1-C6) alkoxy group;

[0048] (d7) a (C1-C6) alkyl halo;

[0049] (d8) a (C2-C6) alkenyl halo;

[0050] (d9) a (C2-C6) alkynyl halo;

[0051] (d10) a halo (C3-C6) cycloalkyl;

[0052] (d11) a halo (C1-C6) alkoxy;

[0053] (d12) a group Ra(Rb)N (wherein Ra and Rb each independently represent a hydrogen atom, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C3-C6) cycloalkyl, (C1-C6) alkyl, phenyl, (C1-C6) alkylcarbonyl or phenyl group)

[0054] (d13) an aryl group;

[0055] (d14) an aryl group having on the ring from one to eight substituents each independently selected from the group consisting of a halogen atom, cyano group, nitro group, (C1-C6) alkyl, (C1-C6) alkoxy, (C3-C6) cycloalkyl, halo (C1-C6) alkyl, halo (C1-C6) alkoxy, halo (C3-C6) cycloalkyl, (C1-C6) alkylthio, (C1-C6) alkylsulfinyl, (C1-C6) alkylsulfonyl, halo (C1-C6) alkylthio, halo (C1-C6) alkylsulfinyl group and halo (C1-C6) alkylsulfonyl;

[0056] (d15) a heteroaryl group;

[0057] (d16) a heteroaryl group having on the ring from one to three substituents each independently selected from the group consisting of a halogen atom, cyano group, nitro group, (C1-C6) alkyl, (C1-C6) alkoxy, (C3-C6) cycloalkyl, halo (C1-C6) alkyl, halo (C1-C6) alkoxy, halo (C3-C6) cycloalkyl, (C1-C6) alkylthio, (C1-C6) alkylsulfinyl group, (C1-C6) alkylsulfonyl, halo (C1-C6) alkylthio, halo (C1-C6) alkylsulfinyl and halo (C1-C6) alkylsulfonyl group;

[0058] (d17) an aryl (C1-C6) alkyl group;

[0059] (d18) a (C1-C6) aryl group an alkyl group having on the ring from one to eight substituents independently selected from the group consisting of a halogen atom, cyano group, nitro group, (C1-C6) alkyl, (C1-C6) alkoxy, (C3-C6) cycloalkyl, halo (C1-C6) alkyl, halo (C1-C6) alkoxy, halo (C3-C6) cycloalkyl group, (C1-C6) alkylthio, (C1-C6) alkylsulfinyl, (C1-C6) alkylsulfonyl, halo (C1-C6) alkylthio, halo (C1-C6) alkylsulfinyl and halo (C1-C6) alkylsulfonyl;

[0060] (d19) a heteroaryl (C1-C6) alkyl;

[0061] (d20) a heteroaryl (C1-C6) alkyl group having on the ring one to three substituents independently selected from the group consisting of a halogen atom, cyano group, nitro group, (C1-C6) alkyl group, (C1-C6) alkoxy, (C3-C6) cycloalkyl, halo (C1-C6) alkyl, halo (C1-C6) alkoxy, halo (C3-C6) cycloalkyl, (C1-C6) alkylthio, (C1-C6) alkylsulfinyl, (C1-C6) alkylsulfonyl, halo (C1-C6) alkylthio, halo (C1-C6) alkylsulfinyl and halo (C1-C6) alkylsulfonyl;

[0062] (d21) a (C1-C6) alkyl group having on the chain thereof one to three substituents independently selected from the group consisting of a cyano group, (C1-C6) alkoxy, Ra(Rb)N (in the formula, Ra and Rb are the same as above), (C1-C6) alkylthio, (C1-C6) alkylsulfinyl and (C1-C6) alkylsulfonyl; or

[0063] (d22) a 3- to 6-membered non-aromatic heterocyclic group having one to two oxygen atoms in the ring.

[0064] Each of X1, X2, X3, and X4 independently indicates

[0065] (e1) a hydrogen atom;

[0066] (e2) a halogen atom;

[0067] (e3) a cyano group;

[0068] (e4) a nitro group;

[0069] (e5) a (C1-C6) alkyl group;

[0070] (e6) a (C3-C6) cycloalkyl group;

[0071] (e7) a (C1-C6) alkoxy group;

[0072] (e8) a halo (C1-C6) alkyl;

[0073] (e9) a halo (C1-C6) alkoxy;

[0074] (e10) a halo (C3-C6) cycloalkyl;

[0075] (e11) a (C1-C6) alkylthio group;

[0076] (e12) a (C1-C6) alkylsulfinyl group;

[0077] (e13) a (C1-C6) alkylsulfonyl group;

[0078] (e14) a (C1-C6) alkylthio halo;

[0079] (e15) a (C1-C6) alkylsulfinyl halo; or

[0080] (e16) a (C1-C6) alkylsulfonyl halo,

[0081] Y indicates an oxygen atom; or a sulfur atom,

[0082] [2] the compound described in [1] or its salts, wherein

[0083] R1 indicates

[0084] (a2) a (C1-C6) alkyl group,

[0085] R2 indicates

[0086] (b1) a hydrogen atom,

[0087] R3 indicates

[0088] (c1) a hydrogen atom;

[0089] (c2) a (C1-C6) alkyl group; or

[0090] (c5) a (C3-C6) cycloalkyl group,

[0091] R4 indicates

[0092] (d2) a (C1-C6) alkyl group;

[0093] (d3) a (C2-C6) alkenyl group;

[0094] (d4) a (C2-C6) alkynyl group;

[0095] (d5) a (C3-C6) cycloalkyl group;

[0096] (d6) a (C1-C6) alkoxy group;

[0097] (d7) a (C1-C6) alkyl halo;

[0098] (d12) a Ra(Rb)N group (in the formula, each of Ra and Rb independently represents a hydrogen atom, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C3-C6) cycloalkyl (C1-C6) alkyl, a phenyl group, (C1-C6) alkylcarbonyl group or phenylcarbonyl group);

[0099] (d13) an aryl group;

[0100] (d14) an aryl group having on the ring from one to eight substituents each independently selected from the group consisting of a halogen atom, cyano group, nitro group, (C1-C6) alkyl, (C1-C6) alkoxy, (C3-C6) cycloalkyl, halo (C1-C6) alkyl, halo (C1-C6) alkoxy, halo (C3-C6) cycloalkyl, (C1-C6) alkylthio, (C1-C6) alkylsulfinyl, (C1-C6) alkylsulfonyl, halo (C1-C6) alkylthio, halo (C1-C6) alkylsulfinyl and halo (C1-C6) alkylsulfonyl;

[0101] (d15) a heteroaryl group;

[0102] (d17) an aryl (C1-C6) alkyl group;

[0103] (d21) a (C1-C6) alkyl group having in the chain one to three substituents, each independently selected from the group consisting of a cyano group, (C1-C6) alkoxy, Ra(Rb)N (in the formula, Ra and Rb are the same as above), (C1-C6) alkylthio, (C1-C6) alkylsulfinyl and (C1-C6) alkylsulfonyl group; or

[0104] (d22) a 3- to 6-membered non-aromatic heterocyclic group having one or two oxygen atoms in the ring,

[0105] each of X1, X2, X3, and X4 independently indicates

[0106] (e1) a hydrogen atom;

[0107] (e2) a halogen atom;

[0108] (e5) a (C1-C6) alkyl group;

[0109] (e7) a (C1-C6) alkoxy group;

[0110] (e11) a (C1-C6) alkylthio group;

[0111] (e12) a (C1-C6) alkylsulfinyl group; or

[0112] (e13) a (C1-C6) alkylsulfonyl group, and

[0113] Y indicates oxygen atom; or sulfur atom,

[0114] [3] the compound described in [1] or [2] or its salts, wherein

[0115] R3 indicates

[0116] (c1) a hydrogen atom; or

[0117] (c2) a (C1-C6) alkyl group,

[0118] each of X1, X2, X3, and X4 independently indicates

[0119] (e1) hydrogen atom;

[0120] (e2) halogen atom; or

[0121] (e7) a (C1-C6) alkoxy group, and

[0122] Y denotes an oxygen atom,

[0123] [4] a fungicide for agrohorticulture which contains, as active ingredient, the compound described in any one of [1] to [3] or salts thereof,

[0124] [5] a method of controlling plant diseases by applying an effective amount of the agrohorticultural fungicide described in [4] to a plant or soil, and

[0125] [6] use of the compound described in any one of [1] to [3] or its salts as a fungicide for agrohorticulture. Effect of the invention

[0126] The present compound of the invention or its salts has a remarkable effect as a fungicide for agrohorticulture. Forms for carrying out the invention

[0127] The terms used in the definition in the general formula (I) of the present compound of the invention are explained below.

[0128] "Halo" means "halogen atom", representing a chlorine atom, bromine atom, iodine atom or fluorine atom;

[0129] "(C1-C6) alkyl group" means a straight or branched chain alkyl group of carbon atom number 1-6, such as a methyl group, ethyl group, normal propyl group, isopropyl group, normal butyl group, iso-butyl group, secondary butyl group, tertiary butyl group, normal pentyl group, iso-pentyl group, tertiary pentyl group, neopentyl group, 2,3-dimethylpropyl group, 1-ethylpropyl group, 1-methylbutyl group, 2-methylbutyl group, normal hexyl group, isohexyl group, 2-hexyl group, 3-hexyl group, 2-methylpentyl group, 3-methylpentyl group, 1,1,2-trimethylpropyl group, 3,3-dimethylbutyl group or the like;

[0130] “(C2-C8) alkenyl” denotes a straight or branched chain alkenyl group of carbon number 2-6, such as, for example, a vinyl group, allyl group, iso-propenyl group, 1-butenyl group, 2-butenyl group, 2-methyl-2-propenyl group, 1-methyl-2-propenyl group, 2-methyl-1-propenyl group, pentenyl group, 1-hexenyl group, 3,3-dimethyl-1-butenyl group, heptenyl group, octenyl group or the like; “(C2-C8)alkynyl” means a straight or branched chain alkynyl group of carbon atom number 2-6, such as, for example, ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 3-methyl-1-propynyl group, 2-methyl-3-propynyl group, pentynyl group, 1-hexynyl group, 3-methyl-1-buynyl group, 3,3-dimethyl-1-butynyl group or the like.

[0131] “(C3-C6) cycloalkyl” means a cyclic alkyl group of carbon atom number 3-6, such as, for example, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group or the like; as “(C1-C6) alkoxy” is included a straight or branched chain alkoxy group of carbon atom number 1-6, such as, for example, methoxy group, ethoxy group, normal propoxy group, isopropoxy group, normal butoxy group, secondary butoxy group, tertiary butoxy group, normal pentyloxy group, isopentyloxy group, tertiary pentyloxy group, neopentyloxy group, 2,3-dimethylpropyloxy group, 1-ethylpropyloxy group, 1-methylbutyloxy group, normal hexyloxy group, isohexyloxy group, 1,1,2-trimethylpropyloxy group or the like;

[0132] a “(C1-C6) alkylthio” group means a straight or branched chain alkylthio at carbon atom number 1-6, such as, for example, a methylthio group, ethylthio group, normal propylthio group, iso-propylthio group, normal butylthio group, secondary butylthio group, tertiary butylthio group, normal pentylthio group, iso-pentylthio group, tertiary pentylthio group, neopentylthio group, 2,3-dimethylpropylthio group, 1-ethylpropylthio group, 1-methylbutylthio group, normal hexylthio group, normal hexylthio group, isohexylthio group, 1,1,2-trimethylpropylthio group or the like;

[0133] “(C1-C6) alkylsulfinyl” means a straight or branched chain alkylsulfinyl group at carbon atom number 1-6, such as, for example, a methylsulfinyl group, sulfinylethyl group, normal sulfinylpropyl group, iso-propyl sulfinyl group, normal butylsulfinyl group, secondary butylsulfinyl group, tertiary butylsulfinyl group, normal pentylsulfinyl group, isopentylsulfinyl group, tertiary pentylsulfinyl group, neopentylsulfinyl group, 2,3-dimethylpropylsulfinyl group, 1-ethylpropylsulfinyl group, 1-methylbutylsulfinyl group, normal hexylsulfinyl group, isohexylsulfinyl group, 1,1,2-trimethylpropylsulfinyl group or the like;

[0134] "(C1-C6) alkylsulfonyl" group indicates a straight or branched chain alkylsulfonyl group at carbon atom number 1-6, such as a methylsulfonyl group, ethylsulfonyl group, normal propylsulfonyl group, isopropylsulfonyl group, normal butylsulfonyl group, secondary butylsulfonyl group, tertiary butylsulfonyl group, normal pentylsulfonyl group, iso-pentylsulfonyl group, tertiary pentylsulfonyl group, neopentylsulfonyl group, 2,3-dimethylpropylsulfonyl group, 1-ethylpropylsulfonyl group, 1-methylbutylsulfonyl group, normal hexylsulfonyl group, isohexylsulfonyl group, 1,1,2-trimethylpropylsulfonyl group or the like.

[0135] “(C1-C6) carbonyl” means an alkylcarbonyl group at carbon atom number 2-7, such as those containing (C1-C6) alkyl group or the like, such as, for example, an acetyl group, propanoyl group, butanoyl group, 2-methylpropanoyl group, pentanoyl group, 2-methylbutanoyl group, 3-methylbutanoyl group, pivaloyl group, hexanoyl group, cyclopropylcarbonyl group or the like described above.

[0136] “(C1-C6) alkoxycarbonyl” denotes an alkoxycarbonyl group at carbon atom number 2-7, such as those containing the (C1-C6) alkoxy group or the like, such as, for example, a methoxycarbonyl group, ethoxycarbonyl group, normal propoxycarbonyl group, isopropoxycarbonyl group, normal butoxycarbonyl group, isobutoxycarbonyl group, secondary butoxycarbonyl group, secondary butoxycarbonyl group, tertiary butoxycarbonyl group, pentyloxycarbonyl group or the like described above.

[0137] In the above-mentioned groups such as “(C1-C6) alkyl”, “(C2-C6) alkenyl”, “(C2-C6) alkynyl”, “(C3-C6) cycloalkyl”, “(C1-C6) alkoxy” or “(C1-C6) alkylthio”, “(C1-C6) alkylsulfinyl” or “(C1-C6) alkylsulfonyl” or the like, at substitutable positions in each group, one or two or more halogen atoms may substitute, and if these groups are substituted by two or more halogen atoms, the halogen atoms may be the same or different. Substituted groups, such halo groups substituted with one or two or more halogen atoms are each denoted as “haloalkyl (C1-C6) alkyl”, “halo(C2-C6) alkenyl”, “haloalkyl (C2-C6) alkynyl”, “haloalkyl (C3-C6) cycloalkyl”, “haloalkyl (C1-C6) alkoxy”, “haloalkyl (C1-C6) alkylthio”, “haloalkyl (C1-C6) alkylsulfinyl” or a “halo(C1-C6) alkylsulfonyl”.

[0138] Expressions such as "(C1-C6)", "(C2-C6)" or "(C3-C6)" or the like define a range of the number of carbon atoms in each substituent. Furthermore, the aforementioned definition also applies to a group to which the aforementioned substituent is attached; for example, in the case of “(C1-C6) alkoxy (C1-C6) alkyl”, what is indicated is that said group is a linear or branched alkoxy group of carbon number 1-6 attached to a linear or branched alkyl group of carbon number 1-6.

[0139] "Aryl group" and "aryl" denote an aromatic hydrocarbon group having a carbon number of 6-10, such as a phenyl group, naphthyl group or the like.

[0140] "Heteroaryl group" and "heteroaryl" denote a monocyclic aromatic heterocyclic group, such as a furyl group, thienyl group, pyridyl group, pyrimidinyl group, pyridazinyl group, pyrazinyl group, pyrrolyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, triazolyl group, tetrazolyl group, triazinyl group or the like.

[0141] "3- to 6-membered non-aromatic heterocyclic group having one to two oxygen atoms in the ring" denotes a non-aromatic heterocyclic group, such as an oxiranyl group, oxetanyl group, tetrahydrofuranyl group, tetrahydropyranyl group, 1,3-dioxolanyl group, 1,3-dioxanyl group, 1,4-dioxanyl group or the like.

[0142] As the salts of the present compound of the invention represented by the general formula (I), for example, inorganic salts such as hydrochloride, sulfate, nitrate, phosphate or the like, organic salts such as acetate, fumarate, malate, oxalate, methanesulfonate, benzenesulfonate, paratoluenesulfonate or the like and salts with inorganic or organic bases such as sodium ion, potassium ion, calcium ion, calcium ion, trimethyl ammonium or the like.

[0143] In some cases, the present inventive compound represented by general formula (I) and its salt have one or more centers of asymmetry in the structural formula and there are two or more enantiomers and diastereomers. The present invention includes all enantiomers and mixtures in which they are comprised in any proportions. Furthermore, the present compound of the invention represented by general formula (I) and a salt thereof, in some cases, has two stereoisomers resulting from the carbon-carbon or carbon-nitrogen double bond in the structural formula, the present invention including all stereoisomers and mixtures in which they are comprised in any proportions.

[0144] For the present inventive compound represented by general formula (I), preferred embodiments are cited as follows.

[0145] As R1, a preferable option is

[0146] (a2) a (C1-C6) alkyl group.

[0147] As R2, a preferable option is

[0148] (b1) a hydrogen atom.

[0149] As R3, a preferable option is,

[0150] (c1) a hydrogen atom;

[0151] (c2) a (C1-C6) alkyl group; or

[0152] (c5) a (C3-C6) cycloalkyl group,

[0153] another preferable option is

[0154] (c1) a hydrogen atom; or

[0155] (c2) a (C1-C6) alkyl group.

[0156] As R4, a preferable option is,

[0157] (d2) a (C1-C6) alkyl group;

[0158] (d3) a (C2-C6) alkenyl group;

[0159] (d4) a (C2-C6) alkynyl group;

[0160] (d5) a (C3-C6) cycloalkyl group;

[0161] (d6) a (C1-C6) alkoxy;

[0162] (d7) a (C1-C6) alkyl halo;

[0163] (d12) a Ra(Rb)N (wherein Ra and Rb each independently represent a hydrogen atom, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C3-C6) cycloalkyl (C1-C6) alkyl, a phenyl group, (C1-C6) alkylcarbonyl or a phenyl group);

[0164] (d13) an aryl group;

[0165] (d14) an aryl group having on the ring from one to eight substituents each independently selected from the group consisting of a halogen atom, cyano group, nitro group, (C1-C6) alkyl, (C1-C6) alkoxy group, (C3-C6) cycloalkyl, halo (C1-C6) alkyl, halo (C1-C6) alkoxy, halo (C3-C6) cycloalkyl, (C1-C6) alkylthio group, (C1-C6) alkylsulfinyl group, (C1-C6) alkylsulfonyl, halo (C1-C6) alkylthio group, halo (C1-C6) alkylsulfinyl group and halo (C1-C6) sulfonyl;

[0166] (d15) a heteroaryl group;

[0167] (d17) an aryl (C1-C6) alkyl group;

[0168] (d21) a (C1-C6) alkyl group having in the chain one to three substituents selected from the group consisting of a cyano group, (C1-C6) alkoxy, Ra(Rb)N (wherein Ra and Rb are the same as above), (C1-C6) alkylthio, (C1-C6) alkylsulfinyl group and (C1-C6) alkylsulfonyl group; or

[0169] (d22) a 3- to 6-membered non-aromatic heterocyclic group having one to two oxygen atoms in the ring.

[0170] As X1, X2, X3, and X4, the preferred options are each independently,

[0171] (e1) a hydrogen atom;

[0172] (e2) a halogen atom;

[0173] (e5) a (C1-C6) alkyl group;

[0174] (e7) a (C1-C6) alkoxy group;

[0175] (e11) a (C1-C6) alkylthio group;

[0176] (e12) a (C1-C6) alkylsulfinyl group; or

[0177] (e13) a (C1-C6) alkylsulfonyl group,

[0178] other preferable options are, each independently,

[0179] (e1) a hydrogen atom;

[0180] (e2) a halogen atom; or

[0181] (e7) a (C1-C6) alkoxy group.

[0182] As Y, a preferable option is an oxygen atom; or a sulfur atom, and a further preferable option is an oxygen atom

[0183] The compounds of the present invention can be produced by the following production methods, for example, but the production methods of the compounds of the present invention are not limited to them. Production Method 1

[0184] (In the formula, R1, R4, X1, X2, X3, X4, and Y are the same as those described for the general formula (I)).

[0185] Of the compounds of the present invention, the compound represented by the general formula (I-1) can be produced according to step [a] below represented by the above-mentioned scheme.

[0186] Step [a] Step for producing a compound represented by the general formula (I-1) by allowing the compound represented by the general formula (1) to react with a compound represented by the general formula (2) and a compound represented by the general formula (3).

[0187] Step [a] a. The compound represented by the general formula (I-1) may be produced by allowing the compound represented by the general formula (1), which may be produced according to a method described in WO2017/055473 A in the presence of an inert solvent, to react with the compound represented by the general formula (2) and the compound represented by the general formula (3).

[0188] The compound represented by general formula (3) that can be used in this reaction (Step [a]) is exemplified by titanium(IV) methoxide, titanium(IV) ethoxide, titanium(IV) n-propoxide, titanium(IV) n-propoxide, i-propoxide, titanium(IV) n-butoxide and titanium(IV) t-butoxide, the consumption amount of which is suitably selectable in the range typically from equimole to five times the mole of the compound represented by general formula (1).

[0189] The inert solvent used in this reaction (Step [a]) may be one that does not appreciably inhibit the progress of this reaction and is exemplified by aliphatic hydrocarbons such as pentane, hexane, and cyclohexane; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as methylene chloride, chloroform, and carbon tetrachloride; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; esters such as ethyl acetate and propyl acetate; nitriles such as acetonitrile and propionitrile; amides such as dimethylformamide and dimethylacetamide; ketones such as acetone and methyl ethyl ketone; and polar aprotic solvent including dimethyl sulfoxide and 1,3-dimethyl-2-imidazolidinone. These inert solvents can be used alone or in a mixture of two or more. The consumption quantity is suitably selectable typically in the range of 0.1 to 100 L, per one mole of the compound represented by general formula (1).

[0190] Since this reaction is an equimolar reaction, equimolar amounts of each reactant may be used and any reactant may be used in excess. The reaction temperature may generally be from room temperature to the boiling point range of the inert solvent used, and the reaction time, which is not constant depending on the reaction scale and reaction temperature, may generally be from a few minutes to 48 hours. After completion of the reaction, the target product may be isolated from the reaction system containing the target product by a common method, and the target product may be obtained by purification by recrystallization, column chromatography or the like when necessary. Production Method 2

[0191] (In the formula, R1, R3, R4, X1, X2, X3, X4, and Y are the same as those described for the general formula (I), and L means a leaving group such as a halogen atom, mesyl group, tosyl group, and triflate group.)

[0192] Of the compounds of the present invention, the compound represented by the general formula (I-2) can be produced according to steps [b] to [e] below represented by the above-mentioned scheme.

[0193] Step [b] Step for producing a compound represented by general formula (5) by allowing a compound represented by general formula (4) to react with the compound represented by general formula (2) and the compound represented by general formula (3).

[0194] Step [c] Step to produce a compound represented by the general formula (7) by allowing the compound represented by the general formula (5) to react with a compound represented by the general formula (6).

[0195] Step [d] Step for producing a compound represented by general formula (9) by allowing the compound represented by general formula (7) to react with hydroxylamine (8).

[0196] Step [e] Step for producing a compound represented by general formula (I-2) by allowing the compound represented by general formula (9) to react with trifluoroacetic acid anhydride (10).

[0197] Step [b]

[0198] The compound represented by the general formula (5) can be produced by allowing the compound represented by the general formula (4) to react with the compound represented by the general formula (2) and the compound represented by the general formula (3) in the presence of an inert solvent.

[0199] The compound represented by general formula (3) that can be used in this reaction is exemplified by titanium (IV) methoxide, titanium (IV) ethoxide, titanium (IV) n-propoxide, titanium (IV) i-propoxide, titanium (IV) i-propoxide, titanium (IV) n-butoxide and titanium (IV) t-butoxide, the consumption amount of which is suitably selectable in the range typically from equimole to five times the mole of the compound represented by general formula (4).

[0200] The inert solvent that may be used in this reaction may be one that does not appreciably inhibit the progress of this reaction and is exemplified by linear or cyclic aliphatic hydrocarbons such as pentane, hexane, and cyclohexane; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as methylene chloride, chloroform, and carbon tetrachloride; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; esters such as ethyl acetate and propyl acetate; nitriles such as acetonitrile and propionitrile; amides such as dimethylformamide and dimethylacetamide; ketones such as acetone and methyl ethyl ketone; and polar aprotic solvents such as dimethyl sulfoxide and 1,3-dimethyl-2-imidazolidinone. These inert solvents can be used alone or in a mixture of two or more. The consumption quantity is suitably selectable typically in the range of 0.1 to 100 L, per one mole of the compound represented by general formula (4).

[0201] Since this reaction is an equimolar reaction, equimolar amounts of each reactant may be used, and any reactant may be used in excess. The reaction temperature may generally be from room temperature to the boiling point range of the inert solvent used, and the reaction time, which is not constant depending on the reaction scale and reaction temperature, may generally be from a few minutes to 48 hours. After completion of the reaction, the target product may be isolated from the reaction system containing the target product by a common method, and the target product may be obtained by purification by recrystallization, column chromatography, or the like when necessary.

[0202] Step [c]

[0203] The compound represented by general formula (7) can be produced by allowing the compound represented by general formula (5) to react with the compound represented by general formula (6) in the presence of a base and an inert solvent.

[0204] The base that can be used in this reaction is exemplified by inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogencarbonate and potassium hydrogencarbonate; alkali metal hydrides such as sodium hydride and potassium hydride; alkali metal alkoxides such as potassium t-butoxide, sodium methoxide and sodium ethoxide; tertiary amines such as triethylamine, diisopropylethylamine and 1,8-diazabicyclo[5.4.0]undec-7-ene; and nitrogen-containing aromatic compounds such as pyridine and dimethylaminopyridine. The consumption amount is suitably selectable typically in the range of equimole to five times the mole of the compound represented by general formula (5).

[0205] The inert solvent that can be used in this reaction can be one that does not considerably inhibit the progress of this reaction and is exemplified by aromatic hydrocarbons such as benzene, toluene and xylene; halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; linear or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane and tetrahydrofuran; esters such as ethyl acetate; amides such as dimethylformamide and dimethylacetamide; ketones such as acetone and methyl ethyl ketone; and polar aprotic solvents such as dimethyl sulfoxide and 1,3-dimethyl-2-imidazolidinone. These inert solvents can be used alone or in a mixture of two or more. The consumption quantity is suitably selectable typically in the range of 0.1 to 100 L, per one mole of the compound represented by the general formula (5).

[0206] Since this reaction is an equimolar reaction, equimolar amounts of each reactant may be used and any reactant may be used in excess. The reaction temperature may generally be from room temperature to the boiling point range of the inert solvent used, and the reaction time, which varies according to the reaction scale and reaction temperature, may be from several minutes to 48 hours. After completion of the reaction, the target product may be isolated from the reaction system containing the target product by a common method, and the target product may be produced by purification by recrystallization, column chromatography or the like when necessary.

[0207] Step [d]

[0208] The compound represented by general formula (9) can be produced by allowing the compound represented by general formula (7) to react with hydroxylamine hydrochloride (8) in the presence of an inert solvent.

[0209] The inert solvent that can be used in this reaction can be one that does not considerably inhibit the progress of this reaction and is exemplified by alcohols such as methanol, ethanol, 1-propanol and 2-propanol; linear or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane and tetrahydrofuran; amides such as dimethylformamide and dimethylacetamide; polar aprotic solvents such as dimethylsulfoxide and 1,3-dimethyl-2-imidazolidinone; and water. These inert solvents can be used alone or in a mixture of two or more. The consumption amount is suitably selectable typically in the range of 0.1 to 100 L, per one mole of the compound represented by general formula (7).

[0210] Since this reaction is an equimolar reaction, equimolar amounts of each reactant may be used, and any reactant may be used in excess. The reaction temperature may generally be from room temperature to the boiling point range of the inert solvent used, and the reaction time, which is not constant depending on the reaction scale and reaction temperature, may generally be from a few minutes to 48 hours. After completion of the reaction, the target product may be isolated from the reaction system containing the target product by a common method, and the target product may be produced by purification by recrystallization, column chromatography, or the like when necessary.

[0211] Step [e]

[0212] The compound represented by the general formula (I-2) can be produced by allowing the compound represented by the general formula (9) to react with trifluoroacetic acid anhydride (10) in the presence of a base and an inert solvent.

[0213] The base that can be used in this reaction is exemplified by inorganic bases such as sodium carbonate, potassium carbonate, sodium hydrogencarbonate and potassium hydrogencarbonate; tertiary amines such as triethylamine, diisopropylethylamine and 1,8-diazabicyclo[5.4.0]undec-7-ene; and nitrogen-containing aromatic compounds such as pyridine and dimethylaminopyridine, the consumption amount of which is suitably selectable in the range typically from equimole to five times the mole of the compound represented by general formula (9).

[0214] The inert solvent that can be used in this reaction can be one that does not considerably inhibit the progress of this reaction and is exemplified by aromatic hydrocarbons such as benzene, toluene and xylene; halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; linear or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane and tetrahydrofuran; esters such as ethyl acetate; amides such as dimethylformamide and dimethylacetamide; ketones such as acetone and methyl ethyl ketone; and polar aprotic solvents such as dimethyl sulfoxide and 1,3-dimethyl-2-imidazolidinone. These inert solvents can be used alone or in a mixture of two or more. The consumption quantity is suitably selectable typically in the range of 0.1 to 100 L, per one mole of the compound represented by the general formula (9).

[0215] Since this reaction is an equimolar reaction, equimolar amounts of each reactant may be used and any reactant may be used in excess. The reaction temperature may generally be from room temperature to the boiling point range of the inert solvent used, and the reaction time, which is not constant depending on the reaction scale and reaction temperature, may generally be from a few minutes to 48 hours. After completion of the reaction, the target product may be isolated from the reaction system containing the target product by a common method, and the target product may be produced by column chromatography or the like purification when necessary. Production Method 3

[0216] (In the formula, R1, R4, X2, X3, X4, and Y are the same as those described for the general formula (I), R5 designates a (C1-C6) alkyl, and n indicates an integer from 1 to 2.)

[0217] Of the compounds of the present invention, the compounds represented by formulas (I-3) and (I-4) can be produced respectively according to steps [f] and [g] and steps [f] to [h] represented by the above-mentioned scheme.

[0218] Step [f] A step to produce a compound represented by the general formula (1-3) by allowing the compound represented by the general formula (1-2) to react with a compound represented by the general formula (10).

[0219] Step [g] Step for producing a compound represented by the general formula (I-3) by allowing the compound represented by the general formula (1-3) to react with the compound represented by the general formula (3) and the compound represented by the general formula (2).

[0220] Step [h] A step to produce a compound represented by general formula (I-4) by oxidizing the compound represented by general formula (I-3).

[0221] Step [f]

[0222] The compound represented by general formula (1-3) can be produced by allowing the compound represented by general formula (1-2) to react with the compound represented by general formula (10) in the presence of an inert solvent.

[0223] The inert solvent that can be used in this reaction can be one that does not considerably inhibit the progress of this reaction and is exemplified by aromatic hydrocarbons such as benzene, toluene and xylene; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; linear or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane and tetrahydrofuran; amides such as dimethylformamide and dimethylacetamide; ketones such as acetone and methyl ethyl ketone; and polar aprotic solvents such as dimethyl sulfoxide and 1,3-dimethyl-2-imidazolidinone. These inert solvents can be used alone or in a mixture of two or more. The consumption amount is suitably selectable typically in the range of 0.1 to 100 L, per one mole of the compound represented by the general formula (1-2).

[0224] Since this reaction is an equimolar reaction, equimolar amounts of each reactant may be used, and any reactant may be used in excess. The reaction temperature may generally be from room temperature to the boiling point range of the inert solvent used, and the reaction time, which is not constant depending on the reaction scale and reaction temperature, may generally be from a few minutes to 48 hours. After completion of the reaction, the target product may be isolated from the reaction system containing the target product by a common method, and the target product may be produced by purification by recrystallization, column chromatography, or the like when necessary.

[0225] Step [g]

[0226] The compound represented by the general formula (I-3) can be produced according to Step [a] of Production Method 1 by allowing the compound represented by the general formula (1-3) to react with the compound represented by the general formula (2) and the compound represented by the general formula (3).

[0227] Step [h]

[0228] The compound represented by general formula (I-4) can be produced by oxidizing the compound represented by general formula (I-3) according to any method commonly employed in chemical synthesis.

[0229] Representative compounds represented by general formula (I) will be listed in Table 1, without restricting the present invention. a. In the table, "Me" indicates a methyl group, "Et" indicates an ethyl group, "n-Pr" indicates an n-propyl group, "i-Pr" indicates an isopropyl group, "c-Pr" indicates a cyclopropyl group, "n-Bu" indicates an n-butyl group, "i-Bu" indicates an isobutyl group, "s-Bu" indicates a secondary butyl group, "t-Bu" indicates a tertiary butyl group, "c-Pen" denotes a cyclopentyl group, and "Ph" indicates a phenyl group. Physical properties indicate a melting point (°C) or refractive index nD (measurement temperature). Table 1 Table 2 Table 1 (Continued) Table 3 Table 1 (Continued) Table 4 Table 1 (Continued) Table 5 Table 1 (Continued) Table 6 Table 1 (Continued) 1) Low polarity diastereoisomer (higher Rf value): Compound No. 135 and Compound No. 138 2) High polarity diastereoisomer (lower Rf value): Compound No. 136 and Compound No. 139 Table 7 Table 1 (Continued)

[0230] The fungicides for agrohorticulture containing the compound represented by the general formula (I) of the present invention or its salts as active ingredient are suitable for the control of diseases occurring in cereals, fruits, vegetables, other crops and ornamental plants.

[0231] Target diseases include filamentous fungal diseases, bacterial diseases, viral diseases or the like. Filamentous fungal diseases that can be recited are, for example, diseases caused by fungi imperfecti (Botry diseases, Helminthosporium, Fusarium, Septoria, Cercospora, Pseudocercosporella, Rhynchosporium, Pyricularia and Alternaria diseases or the like); diseases caused by basidiomycetes (e.g. Hemilelia diseases, Rhizoctonia diseases, Ustilago diseases, Typhula diseases and Puccinia diseases or the like); diseases caused by ascomycota (e.g. Venturia diseases, Podosphaera diseases, Leptosphaeria diseases, Blumeria diseases, Erysiphe diseases, Microdochium diseases, Sclerotinia diseases, Gaeumannomyces diseases, Monilinia diseases and Uninula diseases or the like); and diseases caused by other fungi (e.g. Ascochyta diseases, Phoma diseases, Pythium diseases, Corticium diseases and Pyrenophora diseases or similar. As bacterial diseases that can be recited are, for example, Pseudomonas diseases, Xanthomonas diseases and Erwinia diseases. Viral diseases are cited, for example, diseases such as those caused by tobacco mosaic virus or similar.

[0232] Specific filamentous fungal diseases that may be cited are, for example, rice blast (Pyricularia oryzae), rice sheath blight (Rhizoctonia solani), rice brown spot (Cochiobolus miyabeanus), rice seedling blight (Rhizopus chinensis, Pythium graminicola, Fusarium graminicola, Fusarium roseum, Mucorsp., Phomasp., Tricodermasp.), rice bakanae disease (Gibberella fujikuroi), powdery mildew of barley and wheat or similar (Blumeria graminis), powdery mildew of cucumbers or similar (Sphaerotheca fuliginea), powdery mildew of aubergines or similar (Erysiphe cichoracoarum) and powdery mildew of other host plants, eyespot of barley, wheat or similar (Pseudocercosporella herpotrichoides), wheat spot or similar (Urocystis tritici), snow mould on barley, wheat or similar crops (Microdochium nivalis, Pythium iwayamai, Typhla ishikariensis, Typhla incarnata, Sclerotinia borealis), fusarium ear blight on barley, wheat or similar crops (Fusarium graminearum, Fusarium avenaceum, Fusarium culmorum, Microdoc hium nivalis), rust on barley, wheat or similar crops (Puccinia recondita, Puccinia striiformis, Puccinia graminis), barley, barley or wheat (Gaeumannomyces graminis), crown rust on oats (Puccinia coronata), soybean rust (Phakopsora pachyrhizi) and rust on other plants, grey mould on cucumbers, strawberries or similar crops (Botrytis cinerea), sclerotinic rot on tomatoes, cabbage or similar crops (Sclerotinia sclerotiorum), late blight on potatoes, tomatoes or similar crops (Phytophthora infestans), late blight of other plants, cucumber blight (Pseudoperonospora cubensis), grape blight (Plasmopara viticola), downy mildew of various plants, apple scab (Venturia inaequalis), apple alternaria spot (Alternaria mali), pear black spot (Alternaria kikuchiana), citrus melanose (Diaporthe citri), citrus scab (Elsinoe fawcetti), sugar beet leaf spot (Cercospora beticola), peanut brown leaf spot (Cercospora arachidicola), peanut late blight (Cercospora personata), wheat leaf spot (Septemberoria tritici), wheat glume spot (Leptosphaeria nodorum), barley net spot (Pyrenophora teres), barley stripe (Pyrenophora graminea), barley blight (Rhynchosporium secalis), wheat leaf spot (Ustilago nuda), wheat spot (Tilletia caries), brown spot in grass (Rhizoctonia solani) and dollar spot in grass (Sclerotinia homoeocarpa) or similar.

[0233] Specific bacterial diseases that may be recited are diseases caused by Pseudomonasspp., e.g., bacterial spot of cucumber (Pseudomonas syringae pv. Lachrymans), bacterial wilt disease of tomato (Pseudomonas solanacearum) and bacterial grain rot of rice (Pseudomonas glumae); diseases caused by Xanthomonasspp., e.g., black rot of cabbage (Xanthomonas campestris), bacterial leaf blight of rice (Xanthomonas oryzae) and citrus canker (Xanthomonas citri); and diseases caused by Erwiniaspp., e.g., soft rot of cabbage (Erwinia carotovora) or the like.

[0234] The useful plants in which the present compound of the invention represented by the general formula (I) or its salts can be applied are not particularly limited, and the following plants can be recited as examples hereinafter:

[0235] Cereals (e.g. rice, barley, wheat, rye, oats, corn or the like); beans and peas, such as soybeans, red beans, broad beans, peas, kidney beans, peanuts or the like; fruit trees (e.g. apple, citrus trees and fruit, pear, grape, peach, plum, cherry, walnut, chestnut, almond, banana, strawberry or similar); leafy vegetables and fruits (e.g. cabbage, tomato, spinach, broccoli, lettuce, onion, green onion (chive and Welsh onion), green pepper, eggplant, strawberry, chilli, okra, Chinese chive or similar); root crops (e.g. carrot, potato, sweet potato, taro, radish, lotus rhizome, turnip, burdock, garlic, Chinese chive or similar); processing crops (e.g. cotton, flax, beetroot, hops, sugar cane, beetroot, olive, gum, coffee, tobacco, tea or similar); cucurbitaceous plants (e.g. pumpkin, cucumber, muskmelon, watermelon, cantaloupe or similar); pasture plants (e.g. orchard grass, sorghum, timothy, clover, alfalfa or similar); grasses (e.g. gram-grass, bent grass or the like); perfumery crops (e.g. lavender, rosemary, thyme, parsley, pepper, ginger or the like); flowers and ornamental plants such (e.g. chrysanthemum, rose, carnation, orchid, tulip, lily or the like); garden trees (e.g. ginkgo, cherry, gold-leafed plants or the like); and hardwoods (e.g. white fir, silver fir, pine, hatchet-leaved arbor-vitae, Japanese cedar, Japanese eypress, eucalyptus) or the like.

[0236] The mentioned "plants" also include those to which resistance to HPPD inhibitors such as isoxaflutole, ALS inhibitors such as imazethapyr and thifensulfuron-methyl, EPSP synthetase inhibitors such as glyphosate and glutamine synthetase inhibitors such as glufosinate, acetyl-CoA carboxylase inhibitors such as sethoxydim and herbicides such as bromoxynil, dicamba, 2,4-D or the like has been conferred by a classical breeding method or genetic engineering technique.

[0237] Examples of the "plant" to which resistance has been conferred by a classical breeding method include rape, wheat, sunflower and rice resistant to imidazolinone ALS-inhibiting herbicides such as imazethapyr, which are already commercially available under the product name Clearfield (registered trademark). Similarly, there are soybeans to which resistance to sulfonylurea ALS-inhibiting herbicides such as thifensulfuron-methyl has been conferred by a classical breeding method, which are already commercially available under the product name STS soybean. Similarly, examples to which resistance to acetyl-CoA carboxylase inhibitors such as trione oxime or aryloxyphenoxypropionic acid herbicides has been conferred by a classical breeding method include SR corn.

[0238] The plant and was conferred resistance to acetyl-CoA carboxylase inhibitors is described in the Proceedings of the National Academy of Sciences of the United States of America (Proc. Natl. Acad. Sci. USA), vol. 87, pp. 7175-7179 (1990) or similar. An acetyl-CoA carboxylase variant resistant to an acetyl-CoA carboxylase inhibitor is reported in Weed Science, vol. 53, pp. 728-746 (2005) or similar and a plant resistant to acetyl-CoA carboxylase inhibitors can be generated by introducing a gene for this acetyl-CoA carboxylase variant into a plant by genetic engineering technology or by introducing a variation conferring resistance to acetyl-CoA carboxylase in a plant; Furthermore, plants resistant to acetyl-CoA carboxylase inhibitors or ALS inhibitors or the like can be generated by introducing a site-directed amino acid substitution variation into an acetyl-CoA carboxylase gene or the ALS gene of the plant by introducing a nucleic acid into which a base substitution variation represented by the chimeraplasty technique (Gura T. 1999, Repairing the Genome's Spelling Mistakes, Science 285: 316-318) has been introduced into a plant cell. The present compound of the invention represented by the general formula (I) or its salts can also be used for such plants.

[0239] Furthermore, examples of toxins expressed in such genetically modified crops include: insecticidal proteins derived from Bacillus cereus or Bacillus popilliae; 8-endotoxins such as CrylAb, CrylAc, CrylF, CrylFa2, Cry2Ab, Cry3A, Cry3Bbl or Cry9C derived from Bacillus thuringiensis; insecticidal proteins such as VIP1, VIP2, VIP3 or VIP3A; insecticidal proteins derived from nematodes; animal-generated toxins such as scorpion toxin, spider toxin, bee toxin or insect-specific neurotoxins; mold fungal toxins; plant lectin; agglutinin; protease inhibitors such as a trypsin inhibitor, a serine protease inhibitor, patatin, cystatin or a papain inhibitor; ribosome inactivating proteins (RIPs), such as lycin, corn RIP, abrin, luffin, saporin, or bryodin; steroid metabolizing enzymes, such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glucosyl transferase, or cholesterol oxidase; an ecdysone inhibitor; HMG-CoA reductase; ion channel inhibitors, such as sodium channel inhibitor or calcium channel inhibitor; juvenile hormone esterase; a diuretic hormone receptor; stilbene synthase; bibenzyl synthase; chitinase; and glucanase.

[0240] In addition, the toxins expressed in these genetically modified crops also include: hybrid toxins, partially deleted toxins and modified toxins of δ-endotoxin proteins, such as CrylAb, CrylAc, CrylF, CrylFa2, Cry2Ab, Cy3A, Cry3Bbl, Cry9C, Cry34Ab or Cry35Ab; insecticidal proteins such as VIPl, VIP2, VIP3 or VIP3A. Hybrid toxins are produced from a new combination of the different domains of these proteins, using a genetic engineering technique. As partially deleted toxins, CrylAb comprising a deletion of a portion of an amino acid sequence is known. In modified toxins, one or more amino acids of natural toxins are replaced.

[0241] Examples of such toxins and genetically modified plants capable of synthesizing such toxins are described in EP-A-0 374 753, WO 93/07278, WO 95/34656, EP-A-0 427 529, EP-A-451 878, WO 03/052073 or the like.

[0242] The present agrohorticultural fungicide of the invention can also be used in combination, or systematically, with these technologies.

[0243] In order to control various diseases, the agrohorticultural fungicide present in the invention is applied to the plants on which the diseases are expected to appear, either as it is or in the form of a dilution or suspension in a suitable amount of water or the like in a dosage effective for controlling the diseases. For example, for the purpose of controlling the appearance of diseases in fruit trees, cereals and vegetables, the composition can be used directly for foliage treatment or the composition can also be used for seed treatments, such as seed soaking in the agent solution, seed coating, caliper treatment or the like or root absorption by soil treatment or the like, such as incorporation into the total soil layer, row treatment, soil incorporation, cell seedling treatment, in-hole sting treatment, in-hole sting treatment, plant foot treatment, top dressing, application in rice nursery box, submerged application or the like. Furthermore, application of the present agrohorticultural insecticide of the invention to the nutrient solution in water culture, use by fumigation and injection into tree stems or the like are also usable.

[0244] Furthermore, the present agrohorticultural fungicide of the invention may be used as is or with appropriate dilution with water or the like, or in suspension, in an amount effective for disease control in a location where the disease is expected to occur.

[0245] As a seed treatment method, a method of soaking seeds in a diluted or undiluted liquid preparation of the liquid or solid composition and thereby causing the agent to penetrate the seeds; a method of mixing a solid or liquid preparation with seeds for powder coating and thereby causing the agent to adhere to the seed surface; a method of mixing the preparation with an adhesive carrier such as resin, polymer or the like and coating seeds with this adhesive mixture; a method of spraying the preparation to the vicinity of seeds simultaneously with planting or the like may be referred to.

[0246] "Seeds" to be treated with seed treatment means a plant body of the early stage of cultivation used for the reproduction of plants, covering not only seeds but also plant bodies for the reproduction of nutrients, such as bulb, tuber, seed tuber, stock bud, aerial tubers, scaly bulb or stems for cutting or the like.

[0247] "Soil" or "growing medium" for plants, in the implementation of the method of use of the present invention, means a support for the cultivation of a plant, in particular a support on which the roots grow. Its material quality is not limited, any material being acceptable as long as the plant can grow on it. For example, so-called soils, mattresses, water or the like may be used, specific examples for the material being sand, pumice, vermiculite, diatomaceous earth, agar, gelatinous materials, polymeric materials, rock wool, glass wool, wood chips, bark or the like.

[0248] As a method for spraying onto parts of the foliage of crops or the like, spraying a liquid formulation such as an emulsifiable concentrate, flowable agent or the like or a solid formulation such as a wettable powder or wettable granule or the like having been suitably diluted with water, may refer to dust spraying, fumigation or the like.

[0249] As a method of soil application, applying a liquid preparation diluted in water or undiluted to the base of the plant, nursery bed for planting seedlings or the like, spraying granules on the base of the plant or bed, spraying dust, wettable powder, granules or wettable granules on the soil and mixing with the entire soil before sowing or before transplanting, a powder, wettable powder, wettable granules, granules or the like can be recited in planting holes, planting rows or the like.

[0250] As a method of application in a rice nursery box in a paddy field, even though the form of preparation may vary depending on the time of application, such as application in the sowing period, greening period or transplanting period, in the form of dust, wettable granules, granules or the like can be recited. Application by mixing with soil is also possible, the application of which is by mixing with soil and a powder, granules or wettable granules, examples thereof being mixing into the bed soil, covering the soil or the entire soil. Another possible method is application by simply turning the soil and various formulations into layers.

[0251] For application to a rice field, usually to a rice field in a submerged state, a solid preparation such as a jumbo pack, granules, wettable granules or the like or a liquid formulation such as an emulsifiable or fluid bed concentrate is sprinkled. Otherwise, it is also possible to spray or inject a suitable agent as it is or in the form of a mixture with fertilizers into the soil at the time of transplanting. Furthermore, it is possible to apply the chemical solution of an emulsifiable concentrate to the water inlet or to the water flow source of the irrigation system, whereby a labor-saving application is achieved with the water supplied.

[0252] In the case of upland crops, application to the crop carrier surrounding the seeds or plant bodies in the period between sowing and seedling emergence is available. For plants where the seeds are sown directly in the field, in addition to direct application to the seeds, application to the base of the hills during the growing season is preferable. Sprinkling of granules or irrigation with a liquid formulation after dilution in water or without dilution or similar is possible. Another preferable treatment is to mix granules with crop carriers before sowing and sow the seeds afterwards.

[0253] In cases where the cultivated plants to be transplanted are treated at the time of sowing or in the seedling growing period, in addition to direct treatment on the seeds, irrigation treatment in a seedling growing bed with a liquefied form or with spray granulation is preferable. In addition, applying granules to the planting holes at the time of planting or mixing in the growing carrier in the vicinity of the transplanting sites is also a preferable treatment.

[0254] The present compound of the invention represented by the general formula (I) or its salts is generally used after having been formulated in a form that is convenient in use by the standard method for the formulation of chemical products.

[0255] Namely, the present compound of the invention represented by the general formula (I) or its salts can be used after having been optionally mixed with an adjuvant in a suitable proportion and prepared in a suitable preparation form such as (fluid) suspension, emulsifiable concentrate, oily dispersions, soluble concentrate, wettable powder, wettable granules, granules, powder tablets, packs, jumbos, suspoemulsion or the like through dissolution, separation, suspension, mixing, impregnation, adsorption or gluing.

[0256] The present agrohorticultural fungicides of the invention may contain, in addition to the active ingredient, additive components that are commonly used for agricultural formulations, if necessary. As such additive components, a carrier such as a solid carrier or a liquid carrier, a surfactant, a dispersant, a wetting agent, a binder, an adhesion agent, a thickener, a coloring agent, an extender, a spreader, an antifreeze agent, an anti-caking agent, a disintegrating agent and a stabilizing agent or the like may be recited. Furthermore, an antiseptic agent, plant pieces may be used as additive components, if necessary. These additive components may be used alone or in combination of two or more.

[0257] As a solid carrier, for example, a natural mineral such as quartz, clay, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite or diatomaceous earth; an inorganic salt such as calcium carbonate, ammonium sulfate, sodium sulfate or potassium chloride, synthetic silicic acid or synthetic silicate; an organic solid carrier such as starch, cellulose or plant powder such as sawdust, coconut shell, corn husk and tobacco stalk; a plastic carrier such as polyethylene, polypropylene or polyvinylidene chloride; or urea, inorganic hollow materials, plastic hollow materials and fumed silica such as white carbon may be recited. These may be used alone or in combination of two or more.

[0258] As a liquid carrier, for example, alcohols such as a monohydric alcohol such as methanol, ethanol, propanol, isopropanol and butanol or a polyhydric alcohol such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol or glycerol; a polyhydric alcohol derivative such as propylene-type glycol ether; a ketone such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone and cyclohexanone; an ether such as ethyl ether, dioxane, ethylene glycol monoethyl ether, dipropyl ether and THF; an aliphatic hydrocarbon such as normal paraffin, naphthene, isoparaffin, kerosine or mineral oil; an aromatic hydrocarbon such as benzene, toluene, xylene, solvent naphtha, and alkyl naphthalene; a halogenated hydrocarbon such as dichloroethane, chloroform, and carbon tetrachloride; an ester such as ethyl acetate, diisopropyl phthalate, dibutyl phthalate, dioctyl phthalate, and dimethyl adipate; a lactone such as [gamma]-butyrolactone; an amide such as dimethylformamide, diethylformamide, dimethylacetamide, and N-alkylpyrrolidinone; a nitrile such as acetonitrile; a sulfur compound such as dimethyl sulfoxide; a vegetable oil such as soybean oil, rapeseed oil, cottonseed oil, and castor oil; and water may be recited. These may be used alone or in combination of two or more.

[0259] As surfactants used as dispersant or wetting agent, the following can be mentioned: a nonionic surfactant, such as a sorbitan fatty acid ester, a polyoxyethylene sorbitan fatty acid eater, a sucrose ester, a polyoxyethylene ester, a polyoxyethylene ester, a polyoxyethylene rosin acid ester, a polyoxyethylene fatty acid ester, a polyoxyethylene alkyl ether, a polyoxyethylene alkyl ether, a polyoxyethylene dialkyl phenyl ether, a polyoxyethylene alkyl phenyl ether-formalin condensate, a polyoxyethylene-polyoxypropylene block copolymer, a polyoxyethylene-polyoxypropylene block copolymer, a polyoxyethylene-polyoxypropylene block copolymer, a polyoxyethylene-polyoxypropylene block copolymer, a polyoxyethylene-polyoxypropylene block copolymer, a polyoxyethylene-polyoxypropylene block copolymer, a polyoxyethylene-polyoxypropylene block copolymer, a polyoxyethylene-polyoxypropylene block copolymer, a polyoxyethylene-polyoxypropylene block copolymer, a polyoxyethylene-polyoxypropylene block copolymer, a polyoxyethylene-polyoxyethylene alkylamine block copolymer, a polyoxyethylene fatty acid amide, a polyoxyethylene fatty acid bisphenyl ether, a polyalkylene benzylphenyl ether, a polyoxyalkylene styryl phenyl ether, an acetylenediol, a polyoxyalkylene-added acetylenediol, a polyoxyethylene ether-type silicon, a polyoxyethylene ether-type silicon, a polyoxyethylene ether-type silicon, a polyoxyethylene ether-type silicon and a polyoxyethylene ether-type silicon surfactant, a polyoxyethylene castor oil or a polyoxyethylene hardened mold or oil; an anionic surfactant such as an alkyl sulfate, a polyoxyethylene alkyl ether sulfate, a polyoxyethylene alkylphenyl ether sulfate, a polyoxyethylene styryl phenyl ether sulfate, an alkyl benzenesulfonate, a lignin sulfonate, an alkyl sulfosuccinate, an alkyl naphthalenesulfonate, a naphthalenesulfonate, a sodium alkylnaphthonate formalin condensate of naphthalenesulfonate, a salt of a formalin condensate of an alkylnaphthalenesulfonate, a fatty acid salt, a polycarboxylic acid salt, an N-methyl fatty acid sarcosinate, a rosin acid salt, a rosin acid salt, a polyoxyethylene alkyl ether, and a polyoxyethylene alkylphenyl ether phosphate; a cationic surfactant such as a laurylamine hydrochloride, a stearylamine hydrochloride, an oleylamine hydrochloride, a stearylamine acetate, a stearylaminopropylamine acetate, an alkyltrimethylammonium chloride, and an alkyldimethylbenzalkonium chloride; and an amphoteric surfactant such as an amino acid type or a betaine type. These surfactants may be used alone or in combination of two or more.

[0260] As a binding agent or adhesion agent, for example, carboxymethyl cellulose or its salt, dextrin, water-soluble starch, xanthan gum, guar gum, sucrose, polyvinylpyrrolidone, gum arabic, polyvinyl alcohol, polyvinyl acetate, polysodium acrylate, a polyethylene glycol having an average molecular weight of 6,000 to 20,000, a polyethylene oxide having an average molecular weight of 100,000 to 5,000,000 or a natural phosphatide can be recited.

[0261] As a thickener, for example, a water-soluble polymer such as xanthan gum, guar gum, carboxylmethyl cellulose, polyvinylpyrrolidone, carboxyvinyl polymer, an acrylic polymer, a starch compound or polysaccharide; or an inorganic fine powder such as high-purity bentonite and white carbon may be recited.

[0262] As a coloring agent, for example, an inorganic pigment such as iron oxide, titanium oxide or Prussian blue; and an organic dye such as an arizarin dye, an azo dye or a phthalocyanine metal dye may be recited.

[0263] As an antifreeze agent, for example, a polyhydric alcohol such as ethylene glycol, diethylene glycol, propylene glycol or glycerol can be recited.

[0264] As an additive component for an anti-caking or disintegrating agent, for example, starch, alginic acid, a polysaccharide such as mannose and galactose, polyvinylpyrrolidone, white carbon, ester gum or petroleum resin, sodium tripolyphosphate, sodium hexametaphosphate, stearic acid metal salt, a cellulose powder, dextrin, a methacrylate copolymer, a polyvinylpyrrolidone, a polyaminocarboxylic acid chelate compound, a styrene sulfonate/isobutylene/maleic anhydride copolymer and a starch/polyacrylonitrile graft copolymer.

[0265] As a stabilizer, for example, a drying agent such as zeolite, quicklime and magnesium oxide; an anti-oxidation agent such as a phenol type, an amine type, a sulfur type and a phosphorus type; and an ultraviolet absorber such as a salicylic acid type and a benzophenone type can be cited.

[0266] As an antiseptic, for example, potassium sorbate or 1,2-benzthiazolin-3-one can be recited.

[0267] Furthermore, if necessary, a functional spreader, an activity enhancer such as piperonyl butoxide, an antifreeze agent such as propylene glycol, an antioxidant such as BHT or other additive agents such as a UV absorber may be used.

[0268] The content of the active ingredient compound may vary according to need; the content may suitably be selected from the range of 0.01 to 90 parts by weight per 100 parts by weight of the present agro-horticultural fungicide of the invention. For example, for dusts, granules, emulsifiable concentrates or wettable powders, the suitable content is 0.01 to 50 parts by weight (0.01 to 50% by weight per total weight of the agro-horticultural fungicide).

[0269] The application dosage of the harmful organism control agent of the present invention may be selected in consideration of various factors, such as, for example, a purpose, insect pests to be controlled, growth of a plant, tendency to emergence of insect pests, climate, environmental conditions, preparation form, application method, application site and application time; the dosage of the active ingredient compound may be suitably chosen in a range of 0.001 g to 10 kg, preferably 0.01 g to 1 kg per 10 ares, depending on the purpose.

[0270] When using the agro-cultural fungicide comprising the present inventive compound of general formula (I) or its salts, it is diluted to a concentration suitable for spraying or treated as it is.

[0271] The present inventive agrohorticultural fungicides, in particular, the agrohorticultural insecticide, can be used in admixture with other agrohorticultural insecticides, acaricides, nematocides, fungicides or biological pesticides, in order to expand the spectrum of controllable diseases and pests, prolong the control period or reduce the dosage; furthermore, use in admixture with herbicides, plant growth regulators, fertilizers or the like, depending on the use occasions. Representative compounds are cited below, which does not limit their scope.

[0272] As agro-horticultural fungicides to be used for this purpose, the following agro-cultural fungicides can be recited, for example: aureofungin, azaconazole, azitiram, acypetacs, acibenzolar, acibenzolar-S-methyl, azoxystrobin, anilazine, amisulbrom, ampropylphos, aletocyladol, aldimorph, amobam, isotianil, isovaledione, isopyrazam, isofetamide, isoprothiolane, ipconazole, iprodione, iprovalicarb, iprobenphos, imazalil, iminoctadine, iminoctadine-albesilate, iminoctadine, iminoctadone, iminoctadol, uninacidazole, ethirimol, etem, ethoxyquin, etridiazole, enestroburin, enoxastrobin, enoxastrobin, epoxiconazole, oxadixil, oxathiapiprolin, oxathiapiprolin, oxycarboxin, copper-8-quinolinolate, oxytetracycline, copper ocoxate, oxoconazole, oxoconazole, oxoconazole, oxoconazole, oxoconazole, oxoconazole, oxoconazole, oxoconazole, oxoconazole, oxoconazole, oxoconazole, oxoconazole, oxoconazole, oxoconazole, oxoconazole, cocaine fumarate orisastrobin and soil fungicides such as carbam (metham-sodium); Kasugamicina, carbamorfo, carpropamida, carbendazim, carboxina, carvona, quinazamida, quinacetol, quinoxifeno, chinometionato, quinometionato, captafol, captan, kiralaxil, quinconazol, quintozeno, guazatina, cufraneb, cuprobam, couazodazina, cuprobam, cuazobenzina, metila, clozolinato, clotrimazol, clobentiazona, cloraniformethan, cloranil, clorquinox, cloropicrina, clorfenazol, clorodinitronaftaleno, clorotalonila, cloroneb, salicilanilida, zarilamid, ciazofamida, dietil pirocarbonato, dietofencarbe, ciclafuramid, diclocimet, diclozoline, diclobutrazol, diclofluanida, ciclo-heximida, diclomezina, diclorana, diclorofeno, dichlor, disulfiram, dictatorylimphos, ditianon, diniconazole, diniconazol-M, zineb, dinocap, dinocton, dinosulfon, dinoterbone, dinobuton, dinopenton, dipimetitron, dipimetitron, dipyrithione, diphenylamide, difenoconazole, difenoconazole, difenoconazole, difenoconazole, ciprazole, simeconazole, dimethyrimole, morpho, cymoxanil, dimoxystrobin, ziram, silthiofam, streptomycin, spiroxamine, sultropen, sedaxane, zoxamide, dazomet, thiadiazine, thiadinil, thiadifluor, thiabendazole, thioximide, thiochlorphenifimide, thiophanate, thioflorophenidamide, thiophanate, thiofloropheniamide technazene, teclophthalam, tecoram, tetraconazole, debacarb, dehydroacetic acid, tebuconazole, tebufloquin, dodicin, dodine, DBEDC, dodemorph, drazoxolon, triadimenol, triadimefon, triazbutil, triazotrol, trazipiraz, trazipiraz, trazodichlorodazole, trazimethol oxide, triflumizole, trifloxystrobin, triforine, tolylfluanid, tolclofos-methyl, tolprocarb, natamycin, nabam, nitrostyrene, nitrothal-isopropyl, nuarimol, nonylphenol copper sulfonate, halacrinate, validamycin, piperobutobenzamine, valifenalbutin, bitertanol, hydroxy-isoxazole, hydroisoxazole-potassium, binapacryl, biphenyl, piperalin, h-mexazole, pyroxystrobin, pyracarbolid, pyraclostrobin, pyraziflumid, pyrazofos, pyramethostrobin, pyriophenone, pyridinitrile, pidiflumetofen, pydiflumetofen, pyrisoxazole, pirifenox, piribencarb, pyrimethanil, piroxichlor, piroxifur, piroquilon, vinclozolin, famoxadone, fenapanil, fenamidone, fenaminosulf, fenaminstrobin, fenarimol, itropan, fenoxanil, ferimzone, ferbam, fentin, fenpiclonil, fenpyrazamine, fenbuconazole, fenfuram, fenpropidine, fenpropimorph, fenhexamide, phthalide, butiobate, butylamine, bupyrimate, fuberidazotr, fluamidine, fluamidine fluopicolide, fluopyram, fluoroimide, furcarbanil, fluxapyroxad, fluquinconazole, furconazole, furconazole-cis, fludioxonil, flusilazole, flusulfamide, flutianil, flutolanil, flutriafol, furfural, furmecyclox, flumetover, prumorazid, proquinazole, prolazole, praguazole, propiconazole, propineb, furopanate, probenazole, bromu conazole, hexachlorobutadiene, hexaconazole, hexylthiophos, bethoxazine, il, benalaxyl-M, benodanyl, benomyl, pefurazoate, benquinox, penconazole, benzamorph, pencurur, benzohydroxyenodopyroxamine, fosetyl, fosetyl - Al, polyoxins, polyoxorim, polycarbamate, folpet, formaldehyde, machine oil, maneb, mancozeb, mandipropamide, mandestrobin, myclozolin, myclobutanil, mildiomycin, milneb, mecarbinzid, metasulfocarb, metazoxolon, metam, metam- sodium, metalaxyl, metalaxyl-M, metiram, methyl isothiocyanate, meptylldinocap, metconazole, metosulfovax, metfuroxam, metominostrobin, metrafenone, mepanipyrim, mefenoxam, meptildinocap, mepronil, mebenil, iodomethane, copper chloride, methyl chloride, methyl bromide, copper chloride, methyl bromide, metenedobin, metrafenone, mepanipyrim, mefenoxam, meptildinocap, mepronil, mebenil, iodomethane, copper chloride, methyl chloride, methyl bromide, methanol, methanol; inorganic fungicides such as silver or similar; sodium hypochlorite, cupric hydroxide, wettable sulfur, calcium polysulfide, potassium hydrogen carbonate, sodium hydrogen carbonate, sulfur, copper sulfate anhydride, nickel dimethyldithiocarbamate, copper oxine, zinc sulfate and copper sulfate pentahydrate or similar.

[0273] The following are cited as agrohorticultural insecticides, acaricides and nematocides to be used for the same purpose, for example: 3,5-xylyl methylcarbamate (XMC), Bacillus thuringiensis aizawai, Bacillus thuringiensis israelensis, Bacillus thuringiensis japonensis, Bacillus thuringiensis japonensis, Bacillus or Bacillus thuringiensis tenebrionis, crystal protein toxin produced by Bacillus thuringienses, BPMC, Bt toxin insecticidal compound, CPCBS (chlorfenson, DCIP (dichlorodiisopropyl ether), DD (1, 3-dichloropropene), DDT, NAC., O-4-dimethylsulfame, O-diethyl phosphorothioate (DSP), O-ethyl O-4-nitrophenylphenylphosphonothioate (EPN), tripropylisocyanurate (TPIC), acrinathrin, azadirachtin, azinphos-methyl, acequinocil, acetamiprid, acetoprole, acephate, abramectin, afamectin, afamectin, amidoflumet, amitraz, alanicarb, aldicarb, aldoxycarb, aldrin, alpha-endosulfon, alpha-cypermethrin, albendazole, isazophos, isamidophos, isoamidophos, isoxationion, isofenfos, isoprocarb: MIPC, epsilon-metofluthrin, epsilon-momfluorothrin, ivermectin, imiciafos, imidactoprid, imiprothrin, indoxacarb, esfenvalerate, ethiofencarb, ethion, etiprol, ethoxazole, etopheninoxymethazine, oxidemeton-methyl, oxidoprofos: ESP, oxibendazole, oxfendazole, potassium oleate, sodium oleate, cadusafos, kappa-bifenthrin, cartap, carbaryl, carbosulfon, carbofuryl, gamma-cyhalothrin, xylylcarb, quinalphos, quinofene, chinatoferidine, quinofene, chinatofen, chinatofen, chinatofen, oxodendeton hydrochloride, chromafenozide, chlorantraniliprole, chloroxyphos, chlordimeform, chlordane, chlorpyrifos, chlorpyrifos-methyl, chlorfenapyr, chlorfenson, chlorfenvinphos, chlorfluazuron, chlorobenzilate, chlorobenzoate, chloropraletrophenidin, diaprodent, diaphragm, cypermethrin, dienochlor, cyenopyrenes, dioxabenzophos, diophenol, sigma-cypermethrin, cyclaniliprol, diclofenthion: ECP, cycloprothrin, dichlorvos: DDVP, disulfoton, dinotefuril, cyhalothrin, cyphenothrin, cyfluthrin, diflubenzuron, cyflumetofen, diflovidazine, cy-hexatin, cypermethrin, spirometer, spinaphin, spinaphin, spinaphin, spinaphin, spinach, spinach, spinach, spinach, spinach, spinach, spinach, spinach, spinach, spinach, spinach, spinach and others. Sulfluramide, sulprofos, sulfoxaflor, zeta-cypermethrin, diazinon, tau-fluvalinate, dazomet, thiacloprid, thiamethoxam, thioxazafen, thiodicarb, thiocyclam, tiosultap, tiosultap- sodium, thionazine, thiethrin, tetrazine, tetramine, tetramine, tetramine, tetramine, tetramine, tetramine, tetramine, tetramethrin, pirimphos, tebufenozide, tebufenpirin, tefluthrin, teflubenzuron, demeton-S-methyl, temephos, deltamethrin, terbufos, tralopyril, tralomethrin, transfluthrin, triazamate, trichloriflu nithiazine, nitenpyram, novaluron, noviflumuron, hydroprene, vaniliprole, vamidothion, parathion, parat hion-methyl, halfenprox, halofenozide, bistrifluron, bisultap, hydramethylnon, hydroxypropyl amide, binapacril, piflubumide, bifenazate, bifenthrin, pimethazine, pyraclofos, pyrafluprole, pirififionion, pyridaben, pyridazen, pyridazen, pyridal pirimiphos-methyl, pyrethrins, fipronil, fenazaquin, fenamiphos, to, fenitrothion: MEP, fenoxycarb, fenothiocarb, fenothrin, fenobucarb, fensulfothion, fenthion: MPP, fenthatoate: PAP, fenvalatate, PAP, fenvalerate, fenpyrazinate, fenpyrazate, buprofezin, furatiocarb, pralethrin, fluacripyrim, fluazaindolizine, fluazinam, fluazuron, fluensulfone, fluxametamide, flucicloxuron, flucitrinate, fluvalinate, flufiprole, flupyradifurone, flupyrazofos, flufenerim, flufenoxystrobin, flufenoxuron, flufenzine, flufenoprox, fluproxyfen, flubrocntrinate, fluhexafon, flubendiamide, flumethrin, flurimfen, protiophos, protrifenbut, flonicamid, propargite, BPPS, profenofos, profluthrin, propoxur: PHC, flometoquin, bromopropilate, beta-cyfluthrin, hexaflumuron, hexythiazox, heptafluthrin, heptenophos, permethrin, phosphorated benclothizone, benfotramine, bendiocarb, benzu1, phosfamidon, phosphocarb, phosmet: PMP, polynactins, formethanate, act, machine oil, malathion, milbemycin, milbemycin-A, milbemectin, mecarbam, mesulfenphos, methomyl, metaldehyde, metaflumizone, methamidophos, sodium, metamil methiocarb, metidathion: DMTP, methylisothiocyanate, methylneodecanamide, methylparathion, methoxadaiazone, methoxychlor, methoxyfenozide, metofluthrin, methoprene, metolcarb, meperfluthrin, mevinphos, monocrotophos, monosototin, rinsotin, rotoflutin, levamisole hydrochloride, fenbutatin oxide, morantel tartrate, methyl bromide, cyhexatin, calcium cyanamide, calcium polysulfide, sulfur, nicotine sulfate or similar.

[0274] As herbicides to be used for the same purpose, the following herbicides can be cited, for example: 1-naphthylacetamide, 2, 4-PA, 2,3,6-TBA, 2,4,5-T, 2,4,5-TB, 2,4-D, 2,4-DB, 2,4-DEB, 2,4-DEP, 3,4-DA, 3,4-DB, 3,4-DP, 4-CPA, 4-CPB, 4-CPP, MCP, MCPA, MCPAthioethyl, MCPB, ioxynil, aclonifen, azafenidin, acifluorfen, aziprotrine, azimsulfuron, asulam, acetochlor, atrazine, atraton, anisuron, anilofos, aviglycol amidose, abscisazone, aminocyclopyrachlor, aminopyralid, amibuzin, amiprophos-methyl, ametridione, ametrine, alachlor, alidochlor, aloxidim, alorac, iofensulfuron, isouron, isocarbamide, isoxachlortol, isoxapirifop, isoxenotin, isoxaflutoc, isoxafil, ipazine, ipfencarbazone, iprymidam, imazaquin, , imazapyr, imazametapyr, imazametabenz, imazametabenz-methyl, imazamox, imazethapyr, imazosulfuron, indaziflam, indanofan, indolebutinic acid, eiconazole P- uniconazole, esprocarb, etametsulfuron, etametsulfuron-methyl, etalfluralin, ethiolate, ethyl ethillozate, ethidimuron, etinophen, etephon, ethoxysulfuron, ethoxyfen, etnipromide, etofumesate, ethobenzanide, epronazone oxodazone, oryzalin, orthosulfamuron, orbencarb, cafenstrole, cambendichlor, carbasulam, carfentrazone, carfentrazone-ethyl, karbutylate, carbetamide, carboxazole, quizalofop, quizalofop-P, quizalofop-ethyl, glycerol chlorate, quinoclamine, quinoclamine, quinonamine, glufosinate, glufosinate-P, credazine, clethodim, cloxifonac, clodinafop, clodinafop-propargyl, chlorotoluron, clopyralid, cloproxidim, cloprop, chlorbromuron, clofop, clomazone, clomodoxamil1, clomethoxyphenyl1, -methyl, clorimuzon, ron, chlorimuron-ethyl, chlorosulfuron, chlortal, chlorthiamide, chlortoluron, chlornitrophen, chlorfenac, chlorfenprop, chlorbufam, chlorflurazol, chlorflurenol, chlorprocarb, chlorpropham, chlormequat, chloreturon, chloroxynil, chloroxuron, chloropon, saflufenacil, cyanazine, cyanatrine, dialate, diuron, ida, cyclamide, diuron, dietamide cyclosulfamuron, cyclopyrimorate, dichlorprop, dichlorprop-P, diclobenil, diclofop, diclofop-methyl, dichlormate, dichloralurea, diquat, cisanilide, disul, siduron, Ditopyr, dinitramine, cinidon-ethyl, dinosam, dinosulf, dinosam, cyhalofop-butyl, difenoxuron, difenopenten, difenzoquat, cybutryne, cyprazine, cyprazole, diflufenican, diflufenzopyr, dipropetryn, cypromide, cyperquat, gibberellin, simazine, dimexane, dimethachlor, dimidazon, dimethamethrin, dimethenamid, simetrin, simeton, dimepiperate, dimefuron, cinmethylin, sulgil, capine, sulcotrione, sulfone sulfate, sulfentrazone, sulfosulfuron, sulfometuron, sulfometuron-methyl, secbumeton, sethoxydim, sebuthylazine, terbacyl, daimuron, dazometh, dalapon, thiazafluron, thiazopyr, thiafenacil, thiencarbazone, thiencarbazone-methyl, thiocarbazil, thioclorim, thidiazimin, thidiazuron, thifensulfur, thifensulfuron-methyl, desmedifam, desmethrin, tetrafluron, tenylchlor, tebutame, tebuthiuron, terbumeton, tepraloxidim, tefuryltrione, tembotrione, delachlor, terbacil, terbucarb, terbuchlor, terbutylzilazine, terbutrin, topramezone, tralkoxidim, triasulfu, ron, triaulfuron, triafazidotrazidazine, trichlorodazidazine triflusulfuron, triflusulfuron-methyl, trifluralin, trifloxysulfuron, tripropindan, tribenuron- methyl, tribenuron, trifop, trifopsime, trimeturon, tolpiralate, naptalam, naproanilide, napropamide, nicosulfuron, nitrosulfuron, nitraline, nitralina, nitroprofluorona, nitralina, nitroprofluorona, nitralina, nitrofluorona, paclobutrazol, paraquat, parafluron, haloxidina, halauxifeno, haloxifope, haloxifope-P, haloxifope- metil, halosafen, halosulfuron, halosulfuron-metil, picloram, picolinafena, biciclopirona, ispiribac, bispiribac-sódio, pidanon, pinoxadene, bifenox, piperofos, himexazol, piraclonila, pirasulfotol, pirazoxifeno, pirazossulfuron, pirazosulfuron-etila, pirazolato, bilanafos, piraflufeno-etila, piriclor, piridafol, piritiobac, piritiobac-sodium, piridato, piriftalid, piributicarb, piribenzoxim, pirimisulfan, primisulfuron, pyriminobac-methyl, piroxasulfone, piroxsulam, fenasulam, fenisofam, fenuron, fenoxasulfone, fenoxapropoxyfen fenoprop, phenobenzuron, phenquinotrione, fentiaprop, fenteracol, fentrazamide, phenmedifam, phenmedifam-ethyl, butachlor, butafenacil, butamiphos, buthiuron, butidazole, butylate, buturon, butroxydim, butralin, furoxine, proximal, propyl fluazifop, fluazifop-P, fluazifop-butyl, fluazolate, fluroxypyr, fluotiuron, fluometuron, fluoroglycophene, flurochloridone, fluordiphene, fluoronitrophen, fluoromidine, flucarbazone, flucarbazone-sodium, fluloralin, flucetosulfuron, flutiacet, flutiacet-methyl, flupirsulfuron, flufenacet, flufenican, flufenpir, flupropacil, flupropanate, flupoxum, flumioxacin, fluridone sodium flpropoxate, flurtamone, fluroxypyr, pretilachlor, proxan, proglinazine, procyazine, prodiamine, prosulfalin, prosulfuron, prosulfocarb, propaquizafop, propachlor, propazine, il, propyzamide, propisochlor, prohydrojasmon, propyrisulfuron, propazlazole, propoxycarbazone-sodium, profoxidim, romacil, brompirazone, promethrin, prometon, bromoxynil, bromophenoxime, bromobutide, bromobonil, florasulam, florpirothyroxifene, hexachloroacetone, hexazinone, petetoxamide, penoxsulfam, going, benazoline, penoxsulfamide, benzylaminopurine, benzothiazuron, benzfendizone, bensulide, bensulfon-methyl, benzoylprop, benzobicyclone, benzofenap, benzofluor, bentazone, pentanochlor, benthiocarb, pendimethalin, pentoxazone, benfluralin, benfuresate, fosamine, falesafen, foramsulfuron, forchlorfenuron, tosulfone, mecoprop, mecoprop, mecoprop, mesotrione, mesoprazine, methoprothrin, metazachlor, methazol, metazosulfuron, metabenzothiazuron, metamitron, metamifop, metam, metalpropalin, methiuron, methiozolin, methiobencarb, methyldimonium, methoxurururon, metsulfuron, metsulfamon, metsulfuron, metsulfamon metribuzin, of mepiquat, mefenacet, mefluidide, monalide, monisouron, monuron, monochloroacetic acid, monolinuron, molinate, morphamquat, iodosulfuron, iodosulfuron-methyl-sodium, iodobonil, iodomethane, lactofen, rinuron, linacon peroxide, methyl oxide or similar.

[0275] Furthermore, as biological agrochemicals, the same effect can be achieved by mixed use with the following biological agrochemicals, for example: virus formulations such as nuclear polyhedrosis virus (NPV), granulosis virus (GV), cytoplasmic polyhedrosis virus (CPV), Entomopox virus (EPV) or the like; microbial agrochemicals known as insecticidal or nematocidal agents such as Monacrosporium phymatophagum, Steinernema carpocapsae, Steinernema kushidai and Pasteuria penetrans or the like; microbial agrochemicals used as fungicidal agents such as Trichoderma lignorum, Agrobacterium radiobactor, non-pathogenic Erwinia carotovora and Bacillus subtilis or the like; and biological agrochemicals used as herbicides such as Xanthomonas campestris or the like.

[0276] Furthermore, co-use with biological agrochemicals such as, for example, natural enemies such as the Encarsia wasp (Encarsia formosa), the colemani wasp (Aphidius colemani), the mountain aphid (Aphidoletes aphidimyza), the warm-weather leaf miner (Diglyphus isaea), the leaf miner (Dacnusa sibirica), Persimilis (Phytoseiulus persimilis), spring cocktails (Amblyseius cucumeris), anthocorid predatory insect (Orius sauteri) or the like; microbial agrochemicals such as Beauveria brongniartii; and pheromone agents such as (Z)-10-tetradecenyl=acetate, (E,Z)-4,10-tetradecadienyl=acetate, (Z)-8-dodecenyl=acetate, (Z)-11-tetradecenyl=acetate, (Z)-13-icocene-10-one, 14-methyl-1-octadecene or similar is also possible.

[0277] Representative examples of the present invention are cited, but the present invention is not limited thereto.

[0278] Examples

[0279] EXAMPLE

[0280] Example 1

[0281] Production of N-(methoxy{4-[5-(trifluoromethyl)-1,2,4-oxazol-3-ylphenyl]methyl})butylamide (compound no. 1-13)

[0282] Under an argon atmosphere, 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzaldehyde (0.64 g, 2.7 mmol) produced according to a method described in WO2017/055473 A was dissolved in chloroform (25 mL), to which butylamide (0.28 g, 3.2 mmol) and titanium(IV) methoxide (0.82 g, 4.8 mmol) were added, and the mixture was stirred at room temperature for 17 hours. The mixture was then heated to raise the temperature to 45 °C, stirred for 5 hours, and 0.5 M aqueous potassium carbonate solution was added, and the mixture was stirred for 15 minutes. Ethyl acetate was poured into the mixture, a precipitated solid was filtered off through celite, and the filtrate was condensed under reduced pressure. The obtained residue was purified by column chromatography on silica gel to obtain the title compound (0.25 g, 0.73 mmol).

[0283] Yield: 28%

[0284] Physical property: melting point 151-152 °C

[0285] Example 2

[0286] Production of N-(methoxy{4-[5-(trifluoromethyl)-1,2,4-oxazol-3-ylphenyl]methyl})-N-methylbutylamide (compound No. 1-19)

[0287] N-{[4-(N'-hydroxycarbamimidoyl)phenyl]methoxymethyl}-N-methylbutylamide (0.27 g, 0.96 mmol) was dissolved in chloroform (7 mL), to which pyridine (0.37 g, 4.8 mmol) and trifluoroacetic acid anhydride (0.40 g, 1.9 mmol) were added, and the mixture was stirred at room temperature for 45 min. Water was then added, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate, and condensed under reduced pressure. The obtained residue was purified by column chromatography on silica gel to obtain the title compound (0.24 g, 0.68 mmol).

[0288] Yield: 71%

[0289] Physical property: Refractive index (nD) 1.3559 (20.4 °C)

[0290] Example 3

[0291] Production of N-(methoxy{2-(methylthio)-4-[5-(trifluoromethyl)-1,2,4-oxazol-3-ylphenyl]methyl})butylamide (compound No. 1-132)

[0292] 2-(Methylthio)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzaldehyde (0.48 g, 1.7 mmol) was dissolved in chloroform (12 mL) under an argon atmosphere, and butylamide (0.17 g, 2.0 mmol) and titanium(IV) methoxide (0.51 g, 3.0 mmol) were added and the mixture was stirred at room temperature for 1.5 h. The mixture was then heated to 45 °C, stirred for 3.5 h, and allowed to stand at room temperature for 16 h. The mixture was then heated to 45 °C, stirred for 3 h, and stirred at room temperature for 4 h. The mixture was then heated to 45 °C, stirred for 1 h, and allowed to stand at room temperature for 17.5 h. The mixture was then heated to 45 °C and stirred for 2.5 h. Silica gel was then added, the mixture was stirred for 15 min, and condensed under reduced pressure. The obtained residue was purified by column chromatography on silica gel to obtain the title compound (0.25 g, 0.64 mmol).

[0293] Yield: 39%

[0294] Physical property: melting point 154-155 °C

[0295] Example 4

[0296] Production of N-(methoxy{2-(methylsulfonyl)-4-[5-(trifluoromethyl)-1,2,4-oxazol-3-ylphenyl]methyl})butylamide (compound No. 1-134) and N-(methoxy{2-(methylsulfinyl)-4-[5-(trifluoromethyl)-1,2,4-oxazol-3-ylphenyl]methyl})butylamides (compounds No. 1-135 and 1-136)

[0297] (In the formula, n indicates an integer from 1 or 2.)

[0298] N-(methoxy{2-(methylthio)-4-[5-(trifluoromethyl)-1,2,4-oxazol-3-ylphenyl]methyl})butylamide (0.19 g, 0.48 mmol) was dissolved in chloroform (5 mL), the mixture was cooled to 0 °C, and meta-chloroperbenzoic acid (0.18 g, 0.72 mmol) was added, and the mixture was stirred at room temperature for 5.5 h. Then, saturated aqueous sodium hydrogencarbonate solution was added, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate, and condensed under reduced pressure. The obtained residue was purified by column chromatography over silica gel to obtain the sulfone compound (0.057 g, 0.14 mmol) and two diastereomeric sulfoxide compounds (0.074 g, 0.18 mmol (low polarity diastereomer); 0.064 g, 0.16 mmol (high polarity diastereomer)) indicated in the title.

[0299] Yield: 28% (sulfone compound), 38% (sulfoxide compound, low polarity diastereomer), 33% (sulfoxide compound, high polarity diastereomer)

[0300] Physical property: melting point 158-159 °C (sulfone compound), melting point 148-149 °C (sulfoxide compound, low polarity diastereomer), melting point 177-179 °C (sulfoxide compound, high polarity diastereomer) Reference Example 1

[0301] Production of N-[(4-cyanophenyl)methoxymethyl]butylamide

[0302] 4-Formylbenzonitrile (2.0 g, 15 mmol) was dissolved in chloroform (80 mL) under an argon atmosphere, and butylamide (1.6 g, 18 mmol) and titanium(IV) methoxide (4.7 g, 27 mmol) were added at room temperature, and the mixture was stirred at 45 °C for 3 h. The mixture was then stirred at room temperature for 16 h, heated to 45 °C, and stirred for 6.5 h. To the reaction liquid, a 0.5 M aqueous potassium carbonate solution was added, and the mixture was stirred for 25 min. Ethyl acetate was poured into the mixture, a precipitated solid was separated by filtration through celite, and the filtrate was condensed under reduced pressure. The obtained residue was purified by column chromatography over silica gel to obtain the title compound (2.9 g, 13 mmol).

[0303] Yield: 83% Reference Example 2

[0304] Production of N-[(4-cyanophenyl)methoxymethyl]-N-methylbutylamide

[0305] N-[(4-cyanophenyl)methoxymethyl]butylamide (2.8 g, 12 mmol) was dissolved in tetrahydrofuran (40 mL) and cooled in ice, to which methyl iodide (2.2 g, 16 mmol) and sodium hydroxide (0.62 g, 16 mmol) were added, and the mixture was stirred at room temperature for 3.3 h. The mixture was then cooled to 0 °C, and water was added to quench the reaction, followed by extraction with tert-butyl methyl ether. The organic layer was washed with saturated brine, dried over sodium sulfate, and condensed under reduced pressure. The obtained residue was purified by column chromatography on silica gel to obtain the title compound (1.0 g, 4.2 mmol).

[0306] Yield: 35% Reference Example 3

[0307] Production of N-{[4-(N'-hydroxycarbamimidoyl)phenyl]methoxymethyl}-N-methylbutylamide

[0308] N-[(4-cyanophenyl)methoxymethyl]-N-methylbutylamide (0.96 g, 3.9 mmol) was dissolved in ethanol (15 mL), to which triethylamine (0.99 g, 9.8 mmol) and hydroxylamine hydrochloride (0.68 g, 9.8 mmol) were added, and the mixture was stirred under heating and reflux for 1.5 h. The ethanol was then removed under reduced pressure, water was added, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate, and condensed under reduced pressure to obtain the title compound (1.1 g, 3.9 mmol).

[0309] Yield: stoichiometric Reference Example 4

[0310] Production of 2-(methylthio)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzaldehyde

[0311] 2-Fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzaldehyde (1.0 g, 3.9 mmol) was dissolved in dimethylacetamide (25 mL), to which sodium methyl mercaptide (0.32 g, 4.6 mmol) was added, the mixture was stirred at 45 °C for one hour, and was allowed to stand at room temperature for 17 hours. Water was then added, followed by extraction with MTBE. The organic layer was washed with saturated brine, dried over sodium sulfate, and condensed under reduced pressure. The obtained residue was purified by column chromatography on silica gel to obtain the title compound (0.87 g, 3.0 mmol).

[0312] Yield: 79%

[0313] Physical property: melting point 93-94 °C

[0314] The following examples cite the present inventive formulations. In the formulation examples, the term "parts" indicates "parts by weight". Formulation Example 1.

[0315] An emulsifiable concentrate was prepared by uniformly mixing and dissolving the above ingredients. Formulation Example 2.

[0316] A powder was prepared by uniformly mixing and grinding the above ingredients. Formulation Example 3.

[0317] The granules were prepared by uniformly mixing the above ingredients with an appropriate amount of water and kneading the resulting mixture, followed by granulation and drying. Formulation Example 4.

[0318] A wettable powder was prepared by uniformly mixing and grinding the above ingredients.

[0319] Test example 1. Fungicide efficacy test for soybean rust

[0320] A chemical agent prepared according to Formulation Examples 1 to 4 containing the present compound of the invention represented by general formula (I) as an active ingredient was diluted with water to a predetermined concentration. Soybean (cultivar: Enrei, 2-leaf stage) grown in 6 cm diameter pots was sprayed on foliage at a rate of 10 ml per pot. After air-drying the solution, the spore suspension prepared from spores obtained from soybean leaves infected with rust (Phakopsora pachyrhizi) was inoculated by spray, kept under humidification conditions at 20 °C for 24 hours, and then transferred to a greenhouse to be left for about 10 days.

[0321] For evaluation, various affected area ratios were evaluated to calculate the control value of the following formula 1.

[0322] Evaluation criteria

[0323] 0: control value 9% or lower

[0324] 1: Control value 10-19%

[0325] 2: Control value 20-29%

[0326] 3: Control value 30-39%

[0327] 4: control value 40-49%

[0328] 5: Control value 50-59%

[0329] 6: control value 60-69%

[0330] 7: control value 70-79%

[0331] 8: control value 80-89%

[0332] 9: Control value 90-99%

[0333] 10: Control value 100%

[0334] As a result of the above-mentioned test, of the present inventive compounds represented by the general formula (I), the following compounds showed, at the treatment concentration of 50 ppm, an effect with a control value equal to or greater than 8: 1-7, 1-13, 1-14, 1-15, 1-19, 1-22, 1-25, 1-28, 1-37, 1-39, 1-40, 1-42, 1-43, 1-44, 1-45, 1-46, 1-47, 1-48, 1-49, 1-52, 1-53, 1-54, 1-55, 1-56, 1-57, 1- 58, 162, 1-68, 1-69, 1-71, 1-78, 1-82, 1-95, 1-104, 1-105, 1-106, 1-107, 1-108, 1-109, 1110, 1-111, 1-112, 1-113, 1-114, 1-115, 1-129, 1-130, 1-140, 1-141, 1-142, 1- 143, 1144, 1-145, 1-146, 1-147, 1-148, 1-149, 1-150, 1-151, 1-152, 1-154, 1-155, 1-156, 1157 and 1-158.

[0335] Industrial applicability

[0336] The present compound of the invention, represented by the general formula (I), or its salts has a remarkable effect as a fungicide for agrohorticulture.

Claims (5)

1. Compound, characterized by the general formula (I) or salts thereof, where R1 indicates (a2) a (C1-C6) alkyl group, R2 indicates (b1) a hydrogen atom, R3 indicates (c1) a hydrogen atom; (c2) a (C1-C6) alkyl group; or (c5) a (C3-C6) cycloalkyl group, R4 indicates (d2) a (C1-C6) alkyl group; (d3) a (C2-C6) alkenyl group; (d4) a (C2-C6) alkynyl group; (d5) a (C3-C6) cycloalkyl group; (d6) a (C1-C6) alkoxy group; (d7) a halo (C1-C6) alkyl; (d12) a Ra(Rb)N group (in the formula, each of Ra and Rb independently represents a hydrogen atom, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C3C6) cycloalkyl (C1-C6) alkyl, a phenyl group, (C1-C6) alkylcarbonyl group or phenylcarbonyl group); (d13) a phenyl or naphthyl group; (d14) a phenyl group having on the ring from one to eight substituents each independently selected from the group consisting of a halogen atom, cyano group, nitro group, (C1-C6) alkyl, (C1-C6) alkoxy, (C3-C6) cycloalkyl, halo (C1-C6) alkyl, halo (C1-C6) alkoxy, halo (C3-C6) cycloalkyl, (C1-C6) alkylthio, (C1-C6) alkylsulfinyl, (C1-C6) alkylsulfonyl, halo (C1-C6) alkylthio, halo (C1-C6) alkylsulfinyl and halo (C1-C6) alkylsulfonyl; (d15) a pyridyl group; (d17) a phenyl (C1-C6) alkyl group; (d21) a (C1-C6) alkyl group having in the chain one to three substituents each independently selected from the group consisting of a cyano group, (C1-C6) alkoxy, Ra(Rb)N (in the formula, Ra and Rb are the same as above), (C1-C6) alkylthio, (C1-C6) alkylsulfinyl and (C1-C6) alkylsulfonyl group; or (d22) a 3- to 6-membered non-aromatic heterocyclic group having in the ring one or two oxygen atoms, each of X1 , X2, X3 and X4 independently denotes (e1) a hydrogen atom; (e2) a halogen atom; (e5) a (C1-C6) alkyl group; (e7) a (C1-C6) alkoxy group; (e11) a (C1-C6) alkylthio group; (e12) a (C1-C6) alkylsulfinyl group; or (e13) a (C1-C6) alkylsulfonyl group, and Y indicates oxygen atom. 2. Compound according to claim 1 or its salts, characterized in that R3 indicates (c1) a hydrogen atom; or (c2) a (C1-C6) alkyl group, each of X1, X2, X3 and X4 independently indicates (e1) hydrogen atom; (e2) halogen atom; or (e7) a (C1-C6) alkoxy group, and Y denotes an oxygen atom. 3. Fungicide for agrohorticulture, characterized by the fact that it contains, as active ingredient, the compound as defined in any one of claims 1 or 2 or its salts. 4. A method for controlling plant diseases, characterized in that it is by applying an effective amount of the agrohorticultural fungicide as defined in claim 3, to a plant or soil. 5. Use of the compound as defined in claim 1 or 2 or its salts, characterized by the fact that it is as a fungicide for agrohorticulture.