JP2015214535A - N-alkenyl-substituted amide compound and noxious organism control agent - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a novel noxious organism control agent, particularly a bactericidal agent and a nematicidal agent.SOLUTION: The present invention provides an N-alkenyl-substituted amide compound represented by formula (I) or a salt of the compound, and a noxious organism control agent comprising them. In the formula, Grepresents a structure represented by G-1a, G-3a, G-27a or the like; Xrepresents a halogen atom, difluoromethyl, trifluoromethyl or the like; Yrepresents a halogen atom or the like; Yrepresents a hydrogen atom, a halogen atom, methoxy or the like; Yrepresents a halogen atom, trifluoromethyl or the like; Yrepresents a hydrogen atom, a halogen atom or the like; Rand Rindependently represent a hydrogen atom, a halogen atom, methyl, or the like; Rand Rindependently represent a hydrogen atom, methyl or the like; and Rrepresents a hydrogen atom or the like.

Description

  The present invention relates to a novel N-alkenyl-substituted amide compound and a salt thereof, and a pest control agent containing the compound as an active ingredient.

  Conventionally, regarding N-alkenyl substituted amide compounds, for example, 3-hydroxy-N- (2-phenyl-2-propenyl) benzo [b] thiophene-2-carboxamide (see Patent Document 1), N- (2- Phenyl-2-propenyl) -2-fluorobenzamide (see Non-Patent Document 1), N- [2- [3- (2,5-dioxo-2,5-dihydropyrrol-1-yl) phenyl] -2 -Propenyl] -2-iodo-3-nitrobenzamide (see Non-Patent Document 2), N- (2-phenyl-2-propenyl) -2,4,6-triethylbenzamide (see Non-Patent Document 3), N- [2- (6-chloro-3-pyridyl) -2-propenyl] benzamide (see Non-Patent Document 4) and the like are known.

  However, there is no disclosure regarding N- [2- (substituted pyridin-2-yl) -2-alkenyl] substituted amide compounds according to the present invention, and their usefulness as pest control agents is known. Not.

UK Patent Application Publication No. 2193961

Organic Letters [Organic Lett.] 2014, 16, 3616 Tetrahedron 2009, 65, 4751 Angewante Chemie International Edition [Angew. Chemie, Int. Ed.] 2011, 50, 2593 Tetrahedron Lett. 2006, 62, 12172

  Infections and infestations of pests such as pathogens and parasites can occur when the host is a plant such as a cereal, fruit tree, vegetable, or ornamental plant, resulting in a decrease in crop quality, a significant decrease in yield, and, in some cases, plant death. Cause serious economic losses not only to producers but also to consumers. Therefore, effective control of these pests is a very important issue in order to achieve efficient and stable crop production. In addition, when the host is an animal such as a companion animal, pet animal, livestock, poultry, etc., for the purpose of maintaining the health of the target animal, and when the target animal is livestock, poultry, etc. Effective control of these pests is also an important issue for the purpose of stably producing safe food and high-quality living materials such as wool, feathers and leather. From this point of view, the development of pest control agents for the purpose of controlling pathogenic bacteria and parasites has progressed, and many effective agents have been put to practical use until now.

  However, due to the long-term use of such drugs, in recent years, pathogens and parasites have acquired drug resistance, making it difficult to control with existing pest control agents that have been used. In addition, some existing pest control agents are highly toxic, or some of them remain in the environment for a long time, and the problem of disturbing the ecosystem is becoming apparent. Under such circumstances, development of novel pesticides and effective control methods not only having excellent control activity against pathogenic bacteria and parasites but also having advanced control characteristics such as low toxicity and low persistence has always been made. Expected.

  As a result of intensive research aimed at solving the above problems, the present inventors have found that a novel N-alkenyl-substituted amide compound represented by the following formula (I) has excellent pest control activity, particularly antifungal / killing activity. The present invention was completed by discovering that it is a very useful compound that exhibits nematode activity and has almost no adverse effect on non-target organisms such as plants, mammals, fish, useful insects and natural enemies.

  That is, the present invention relates to the formula (I):

Wherein, G ¹ represents a structure represented by G ¹ -1~G ¹ -51,

W represents an oxygen atom or a sulfur atom,
X ¹ represents a halogen atom, nitro, C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl,
X ² represents a hydrogen atom or a halogen atom,
X ³ represents a hydrogen atom or C ₁ -C ₄ alkyl,
Y ¹ represents a halogen atom, cyano, nitro, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy or C ₁ -C ₄ alkylthio,
Y ² is hydrogen atom, halogen atom, cyano, methyl, trifluoromethyl, C ₁ -C ₄ alkoxymethyl, C ₁ -C ₄ alkylthiomethyl, C ₁ -C ₄ alkylsulfinylmethyl, C ₁ -C ₄ alkylsulfonyl represents methyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy or _C 1 -C ₄ alkylthio,
Y ³ represents a hydrogen atom, a halogen atom, cyano, nitro, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₂ -C ₄ alkenyl, C ₂ -C ₄ haloalkenyl, -OR ⁷ , -S ( ^{_{O) r R 7, -C (}} R 8) = NOR 9, -C (O) NH 2, -C (S) NH 2, D-3, D-7, D-11, D-22, D- Represents 28 or D-29,
Y ⁴ represents a hydrogen atom, a halogen atom, cyano or methyl,
D-3, D-7, D-11, D-22, D-28 and D-29 each represent an aromatic heterocycle represented by the following structural formula;

Z is a halogen atom, cyano, nitro, C ₁ -C ₄ alkyl, trifluoromethyl, methoxy, difluoromethoxy, trifluoromethoxy, methylthio, methylsulfinyl, methylsulfonyl, trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethyl When sulfonyl or phenyl is represented and m or n represents 2 or more, each Z may be the same as or different from each other. Furthermore, when two Zs are adjacent, they are adjacent. The two Z's may form a 6-membered ring with the carbon atom to which each Z binds by forming -CH = CH-CH = CH-
R ¹ and R ² are each independently a hydrogen atom, a halogen atom, nitro, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₃ -C ₆ cycloalkyl (C ₁ -C ₄ ) alkyl, C ₁ -C ₄ alkoxy _(C 1 ~C ₄₎ represents alkyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₄ alkoxy or _C 1 -C ₄ haloalkoxy,
R ³ and R ⁴ are each independently a hydrogen atom, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxymethyl, C ₁ -C ₄ alkylthiomethyl, C ₁ -C ₄ alkyl sulfinyl methyl or C ₁ -C ₄ alkylsulfonyl or represents methyl,
Alternatively, R ³ and R ⁴ together form an ethylene chain to form a cyclopropyl ring with the carbon atom to which R ³ and R ⁴ are bonded,
R ⁵ is a hydrogen atom, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, (C ₁ -C ₂ ) alkyl substituted by R ¹⁰ , C ₃ -C ₆ cycloalkyl, C ₂ -C ₄ alkenyl. , C ₃ -C ₄ alkynyl, -OH, C ₁ ~C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ haloalkylthio, -C a ^{(O) R 11} or _C 1 -C ₄ alkoxycarbonyl Represent,
R ⁶ represents C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl,
R ⁷ is C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy (C ₁ -C ₂ ) alkyl, E-5, E-14, C ₃ -C ₄ alkenyl, C ₃ -C ₄ represents haloalkenyl, C ₃ -C ₄ alkynyl, C ₃ -C ₄ haloalkynyl, phenyl substituted by phenyl or _{(Z) m,}
E-5 and E-14 each represent a saturated heterocyclic ring represented by the following structural formula,

R ⁸ represents a hydrogen atom or C ₁ -C ₄ alkyl,
R ⁹ represents C ₁ -C ₄ alkyl,
R ¹⁰ represents cyano, —OR ¹³ , C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkoxycarbonyl, —C (O) NH ₂ or —C (S) NH ₂ ,
R ¹¹ represents C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxymethyl, C ₃ -C ₄ cycloalkyl or C ₂ -C ₄ alkenyl,
R ¹² represents C ₁ -C ₄ alkyl, and when p represents 2, each R ¹² may be the same as or different from each other;
R ¹³ represents C ₁ -C ₄ alkyl, C ₂ -C ₄ haloalkyl, C ₁ -C ₄ alkylcarbonyl, C ₃ -C ₆ cycloalkylcarbonyl or C ₁ -C ₄ alkoxycarbonyl,
m represents 1, 2, 3, 4 or 5;
n represents 0, 1, 2, 3 or 4;
p represents 0, 1 or 2;
r represents 0, 1 or 2. ]
N-alkenyl substituted amide compounds represented by the following formulas, N-oxides or salts thereof, all stereoisomers thereof, intermediates for their production, and pest control agents containing them as active ingredients.

  The compound of the present invention represented by the formula (I) and a pest control agent containing the compound as an active ingredient are excellent control for pests in the fields of agriculture, horticulture, livestock and hygiene, especially fungi and linear animals. It exerts its effect and exerts a sufficient control effect against those pests that have acquired resistance to existing drugs. Furthermore, it has almost no adverse effect on non-target organisms such as plants, mammals, fish, useful insects and natural enemies, and has low persistence and a low environmental burden.

  Therefore, the present invention can provide a useful novel pest control agent.

  The N-alkenyl-substituted amide compound represented by the formula (I) included in the present invention has an optically active substance resulting from the presence of one or more asymmetric carbon atoms depending on the substituent. However, the present invention encompasses all optically active forms or racemates. Further, in the compounds included in the present invention, there are cases where geometric isomers of E-form and Z-form may exist depending on the substituent, but the present invention is not limited to these E-form, Z-form or E-form. And a mixture containing the Z-form in an arbitrary ratio.

  Examples of the halogen atom in the present specification include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom. In the present specification, the notation “halo” also represents these halogen atoms.

  In the specific description of the substituents in the present specification, the notation “n-” is “normal”, “i-” is “iso”, “s-” is “secondary”, “tert-” "Means" tertiary ".

In the present specification, “C _a -C _b alkyl” represents a linear or branched hydrocarbon group having _a to _b carbon atoms, such as a methyl group, an ethyl group, or n-propyl. Specific examples include groups, i-propyl groups, n-butyl groups, i-butyl groups, s-butyl groups, tert-butyl groups, pentyl groups, 1-ethylpropyl groups, 2,2-dimethylpropyl groups, hexyl groups, etc. Each selected within a range of each specified number of carbon atoms.

In the present specification, the expression “C _a -C _b haloalkyl” is a linear or branched chain having a carbon number of _a to _b, wherein a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom. In this case, when substituted by two or more halogen atoms, these halogen atoms may be the same as or different from each other. For example, fluoromethyl group, chloromethyl group, bromomethyl group, iodomethyl group, difluoromethyl group, dichloromethyl group, trifluoromethyl group, chlorodifluoromethyl group, trichloromethyl group, bromodifluoromethyl group, 1-fluoroethyl group, 2- Fluoroethyl group, 2-chloroethyl group, 2-bromoethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, 2-chloro-2,2-difluoroethyl group, 2,2,2 -Trichloroethyl group, 2-bromo-2,2-difluoroethyl group, 1,1,2,2-tetrafluoroethyl group, 2-chloro-1,1,2-trifluoroethyl group, pentafluoroethyl group, 2,2-difluoropropyl group, 3,3,3-trifluoropropyl group, 3-bromo-3,3-difluoropropyl group, 2,2,3,3-tetrafluoropropyl group, , 2,3,3,3-pentafluoropropyl group, 1,1,2,3,3,3-hexafluoropropyl group, heptafluoropropyl group, 2,2,2-trifluoro-1- (methyl) Ethyl group, 2,2,2-trifluoro-1- (trifluoromethyl) ethyl group, 1,2,2,2-tetrafluoro-1- (trifluoromethyl) ethyl group, 2,2,3,4 Specific examples include 2,4,4-hexafluorobutyl group, 2,2,3,3,4,4,4-heptafluorobutyl group, nonafluorobutyl group, etc., each having a specified number of carbon atoms Selected.

In the present specification, the expression “C _a -C _b cycloalkyl” represents a cyclic hydrocarbon group having _a to _b carbon atoms and represents a monocyclic or complex ring structure having 3 to 10 members. Can be formed. Each ring may be optionally substituted with an alkyl group within the range of the specified number of carbon atoms. Specific examples include cyclopropyl group, cyclobutyl group, 1-methylcyclopropyl group, 2-methylcyclopropyl group, cyclopentyl group, 2,2-dimethylcyclopropyl group, 1-methylcyclobutyl group, cyclohexyl group and the like. , Each selected range of carbon atoms.

In the present specification, the expression “C _a -C _b alkenyl” is a linear or branched chain consisting of _a to _b carbon atoms, and one or more double bonds in the molecule. An unsaturated hydrocarbon group having, for example, vinyl group, 1-propenyl group, 2-propenyl group, 1-methylethenyl group, 1-butenyl group, 2-butenyl group, 1-methyl-1-propenyl group, 2-methyl Specific examples include a -1-propenyl group, a 2-methyl-2-propenyl group, a 3-methyl-3-butenyl group, and the like, and each is selected within the range of the designated number of carbon atoms.

In the present specification, the expression “C _a -C _b haloalkenyl” is a linear or branched chain having a carbon number of _a to _b in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom And an unsaturated hydrocarbon group having one or more double bonds in the molecule. At this time, when substituted by two or more halogen atoms, these halogen atoms may be the same as or different from each other. For example, 2-fluorovinyl group, 2-chlorovinyl group, 1,2-dichlorovinyl group, 2,2-dichlorovinyl group, 2,2-dibromovinyl group, 2-fluoro-2-propenyl group, 2-chloro- 2-propenyl group, 3-chloro-2-propenyl group, 3,3-difluoro-2-propenyl group, 2,3-dichloro-2-propenyl group, 3,3-dichloro-2-propenyl group, 2,3 1,3-trifluoro-2-propenyl group, 2,3,3-trichloro-2-propenyl group, 1- (trifluoromethyl) ethenyl group, 4,4-difluoro-3-butenyl group, 3,4,4 Specific examples include -trifluoro-3-butenyl group, 2,4,4,4-tetrafluoro-2-butenyl group, 3-chloro-4,4,4-trifluoro-2-butenyl group, and the like. Each selected range of carbon atoms is selected.

In the present specification, the expression “C _a -C _b alkynyl” is linear or branched consisting of _a to _b carbon atoms and has one or more triple bonds in the molecule. Represents an unsaturated hydrocarbon group such as ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group, 1-pentynyl group Specific examples include 2-pentynyl group, 1-hexynyl group, 3-hexynyl group, 3-methyl-1-pentynyl group, 4-methyl-1-pentynyl group, 3,3-dimethyl-1-butynyl group, etc. Selected within a range of each specified number of carbon atoms.

In the present specification, the expression “C _a -C _b haloalkynyl” refers to a linear or branched chain having a carbon number of _a to _b in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom And an unsaturated hydrocarbon group having one or more triple bonds in the molecule. At this time, when substituted by two or more halogen atoms, these halogen atoms may be the same as or different from each other. For example, 2-chloroethynyl group, 2-bromoethynyl group, 2-iodoethynyl group, 3-fluoro-1-propynyl group, 3-chloro-1-propynyl group, 3-chloro-2-propynyl group, 3-bromo- 1-propynyl group, 3-bromo-2-propynyl group, 3-iodo-2-propynyl group, 3,3-difluoro-1-propynyl group, 3,3,3-trifluoro-1-propynyl group, 3- Specific examples include a bromo-1-butynyl group, a 3-fluoro-3-methyl-1-butynyl group, a 3-chloro-3-methyl-1-butynyl group, and a 3-bromo-3-methyl-1-butynyl group. Each of which is selected for each specified number of carbon atoms.

The expression “C _a -C _b alkoxy” in the present specification represents an alkyl-O— group having the above-mentioned meaning consisting of _a to _b carbon atoms, for example, methoxy group, ethoxy group, n-propyloxy. Groups, i-propyloxy groups, n-butyloxy groups, i-butyloxy groups, s-butyloxy groups, tert-butyloxy groups, pentyloxy groups, hexyloxy groups, etc. The range is selected.

In the present specification, the expression “C _a -C _b haloalkoxy” represents a haloalkyl-O— group having the above-mentioned meaning consisting of _a to _b carbon atoms, such as a difluoromethoxy group, a trifluoromethoxy group, Chlorodifluoromethoxy group, bromodifluoromethoxy group, 2-fluoroethoxy group, 2-chloroethoxy group, 2,2,2-trifluoroethoxy group, 1,1,2,2, -tetrafluoroethoxy group, 2-chloro Specific examples include -1,1,2-trifluoroethoxy group, 1,1,2,3,3,3-hexafluoropropyloxy group, and the like, and each is selected within the range of each designated number of carbon atoms. .

In the present specification, the expression “C _a -C _b alkylthio” represents an alkyl-S— group having the above-mentioned meaning consisting of _a to _b carbon atoms, for example, methylthio group, ethylthio group, n-propylthio group. Specific examples include i-propylthio group, n-butylthio group, i-butylthio group, s-butylthio group, tert-butylthio group, and the like, and each is selected within the range of the designated number of carbon atoms.

In the present specification, the expression “C _a -C _b haloalkylthio” represents a haloalkyl-S— group having the above-mentioned meaning consisting of _a to _b carbon atoms, such as a difluoromethylthio group, a trifluoromethylthio group, Chlorodifluoromethylthio group, trichloromethylthio group, bromodifluoromethylthio group, 2,2,2-trifluoroethylthio group, 1,1,2,2-tetrafluoroethylthio group, 2-chloro-1,1,2,2- Trifluoroethylthio group, pentafluoroethylthio group, 1,1,2,3,3,3-hexafluoropropylthio group, heptafluoropropylthio group, 1,2,2,2-tetrafluoro-1- ( Specific examples include a trifluoromethyl) ethylthio group, a nonafluorobutylthio group, and the like, and each is selected within the range of the designated number of carbon atoms.

In the present specification, the expression “C _a -C _b alkylsulfinyl” represents an alkyl-S (O) — group having the above-mentioned meaning consisting of _a to _b carbon atoms, such as methylsulfinyl group, ethylsulfinyl group. Group, n-propylsulfinyl group, i-propylsulfinyl group, n-butylsulfinyl group, i-butylsulfinyl group, s-butylsulfinyl group, tert-butylsulfinyl group, etc. It is selected in the range of the number of atoms.

In the present specification, the expression “C _a -C _b alkylsulfonyl” represents an alkyl-S (O) ₂ -group having the above-mentioned meaning consisting of _a to _b carbon atoms, such as a methylsulfonyl group, ethyl Specific examples include a sulfonyl group, n-propylsulfonyl group, i-propylsulfonyl group, n-butylsulfonyl group, i-butylsulfonyl group, s-butylsulfonyl group, tert-butylsulfonyl group, and the like. Selected in the range of the number of carbon atoms.

In the present specification, the notation of “tri (C _a -C _b alkyl) silyl” is substituted by an alkyl group having the above-mentioned meanings each having the same or different number of carbon atoms from _a to _b. For example, trimethylsilyl group, triethylsilyl group, tri (n-propyl) silyl group, ethyldimethylsilyl group, n-propyldimethylsilyl group, n-butyldimethylsilyl group, i-butyldimethylsilyl group, Specific examples include a tert-butyldimethylsilyl group and the like, which are selected in the range of each designated number of carbon atoms.

In the present specification, the expression “C _a -C _b alkylcarbonyl” represents an alkyl-C (O) — group having the above-mentioned meaning consisting of _a to _b carbon atoms, for example, an acetyl group, a propionyl group, Specific examples include butyryl group, isobutyryl group, valeryl group, isovaleryl group, 2-methylbutanoyl group, pivaloyl group, etc., and each is selected within the range of the designated number of carbon atoms.

In the present specification, the expression “C _a -C _b cycloalkylcarbonyl” represents a cycloalkyl-C (O) — group having the above-mentioned meaning consisting of _a to _b carbon atoms, for example, a cyclopropylcarbonyl group , Cyclobutylcarbonyl group, 1-methylcyclopropylcarbonyl group, 2-methylcyclopropylcarbonyl group, cyclopentylcarbonyl group, 2,2-dimethylcyclopropylcarbonyl group, cyclohexylcarbonyl group, etc. In the range of the number of carbon atoms.

In the present specification, the expression “C _a -C _b alkoxycarbonyl” represents an alkyl-OC (O) — group having the above-mentioned meaning consisting of _a to _b carbon atoms, for example, methoxycarbonyl group, ethoxycarbonyl Specific examples include a group, n-propyloxycarbonyl group, i-propyloxycarbonyl group, n-butoxycarbonyl group, i-butoxycarbonyl group, tert-butoxycarbonyl group, etc. Selected.

In the present specification, the expression “C _a -C _b alkylcarbonyloxy” represents an alkyl-C (O) —O— group having the above-mentioned meaning consisting of _a to _b carbon atoms, for example, an acetyloxy group Specific examples thereof include propionyloxy group, butyryloxy group, isobutyryloxy group, and the like, and each is selected within the range of the designated number of carbon atoms.

The expression “C _a -C _b alkylsulfonyloxy” in the present specification represents an alkylsulfonyl-O— group having the above-mentioned meaning consisting of _a to _b carbon atoms, such as methylsulfonyloxy group, ethylsulfonyl Specific examples include an oxy group, an n-propylsulfonyloxy group, an i-propylsulfonyloxy group, and the like, and each is selected within the range of the designated number of carbon atoms.

In the present specification, “C _a -C _b alkoxymethyl”, “C _a -C _b alkylthiomethyl”, “C _a -C _b alkylsulfinylmethyl”, “C _a -C _b alkylsulfonylmethyl”, “C _a- The notation “C _b cycloalkyl (C _d -C _e ) alkyl” or “C _a -C _b alkoxy (C _d -C _e ) alkyl” is any C _a -C _b cycloalkyl group having the above-mentioned meaning, respectively. , A hydrogen atom optionally bonded to a carbon atom by a C _a -C _b alkoxy group, a C _a -C _b alkylthio group, a C _a -C _b alkylsulfinyl group or a C _a -C _b alkylsulfonyl group Represents a group or an alkyl group having the above-mentioned meaning consisting of d to e, and is selected in the range of each designated number of carbon atoms.

In the present specification, the notation “(C _a -C _b ) alkyl substituted by R ¹⁰ ” indicates that the number of carbon atoms in which a hydrogen atom bonded to a carbon atom is substituted by any R ¹⁰ is from _a to _b. The above-mentioned meaning is an alkyl group, and each is selected within the range of the designated number of carbon atoms.

In the present specification, the expression “hydroxy (C _d -C _e ) cycloalkyl” is the above-mentioned meaning that the number of carbon atoms in which a hydrogen atom bonded to a carbon atom is substituted by a hydroxyl group is _d to _e. Represents an alkyl group and is selected within each specified number of carbon atoms.

In the compounds included in the present invention, examples of the preferred range of the substituent represented by G ¹ include the following groups.

That is, G ¹ -I: G ¹ -1 [where X ¹ represents trifluoromethyl and X ² represents a hydrogen atom. ].

G ¹ -II: G ¹ -2 [where X ¹ represents trifluoromethyl. ].

G ¹ -III: G ¹ -3 [where X ¹ represents a halogen atom, difluoromethyl or trifluoromethyl, and X ² represents a hydrogen atom. ].

G ¹ -IV: G ¹ -11 [where X ¹ represents methyl. ].

G ¹ -V: G ¹ -27 [where X ¹ represents difluoromethyl, X ² represents a hydrogen atom, and R ⁶ represents methyl. ].

G ¹ -VI: G ¹ -33 [wherein X ¹ represents difluoromethyl or trifluoromethyl, and X ³ represents methyl. ].

G ¹ -VII: G ¹ -1 [wherein X ¹ represents a halogen atom, methyl or difluoromethyl, and X ² represents a hydrogen atom. ].

G ¹ -VIII: G ¹ -1 [where X ¹ and X ² each independently represent a fluorine atom or a chlorine atom. ].

G ¹ -IX: G ¹ -2 [where X ¹ represents a halogen atom or difluoromethyl. ].

G ¹ -X: G ¹ -3 [where X ¹ represents methyl and X ² represents a hydrogen atom. ].

G ¹ -XI: G ¹ -7 [where X ¹ represents a halogen atom, methyl, difluoromethyl or trifluoromethyl. ].

G ¹ -XII: G ¹ -8 [wherein X ¹ represents trifluoromethyl, and X ³ represents a hydrogen atom or methyl. ].

G ¹ -XIII: G ¹ -9 [wherein X ¹ represents difluoromethyl or trifluoromethyl, X ² represents a hydrogen atom, and X ³ represents a hydrogen atom or methyl. ].

G ¹ -XIV: G ¹ -11 [where X ¹ represents a halogen atom, difluoromethyl or trifluoromethyl. ].

G ¹ -XV: G ¹ -12 [where X ¹ represents a halogen atom, difluoromethyl or trifluoromethyl, and X ² represents a hydrogen atom. ].

G ¹ -XVI: G ¹ -13 [where X ¹ represents a halogen atom, difluoromethyl or trifluoromethyl, and X ² represents a hydrogen atom. ].

G ¹ -XVII: G ¹ -16 [wherein X ¹ represents difluoromethyl or trifluoromethyl, X ² represents a hydrogen atom, and R ⁶ represents methyl. ].

G ¹ -XVIII: G ¹ -27 [where X ¹ represents trifluoromethyl, X ² represents a hydrogen atom, and R ⁶ represents methyl. ].

G ¹ -XIX: G ¹ -27 [where X ¹ represents methyl, difluoromethyl or trifluoromethyl, X ² represents a fluorine atom or a chlorine atom, and R ⁶ represents methyl. ].

G ¹ -XX: G ¹ -32 [where X ¹ represents difluoromethyl or trifluoromethyl, and X ³ represents a hydrogen atom or methyl. ].

G ¹ -XXI: G ¹ -33 [wherein X ¹ represents difluoromethyl or trifluoromethyl, and X ³ represents a hydrogen atom. ].

G ¹ -XXII: G ¹ -44 [where X ¹ represents difluoromethyl or trifluoromethyl, and R ⁷ represents methyl. ].

G ¹ -XXIII: G ¹ -50 [wherein X ¹ represents methyl or trifluoromethyl, and r represents 0, 1 or 2. ].

Of these, ^{G 1} -I~G ¹ -VI as range of the substituent of ^{G 1, G 1 -VII~G 1 -IX} , G 1 -XI, G 1 -XIV, G 1 -XV and ^{G 1 -XVII~G} more preferably ¹ -XX, ^{further, G 1 -I~G 1 -III, G} 1 -V, G 1 -VI, G 1 -IX, G 1 -XI, G 1 -XIV , G ¹ -XV, G ¹ -XVIII and G ¹ -XIX are particularly preferred.

In the compounds included in the present invention, examples of combinations of preferred ranges of substituents represented by Y ¹ , Y ² , Y ³ and Y ⁴ include the following groups YI to Y-III.

That is, YI: Y ¹ is a halogen atom, Y ² is a hydrogen atom, Y ³ is a halogen atom and trifluoromethyl, and Y ⁴ is a hydrogen atom.

Y-II: Y ¹ is a halogen atom, Y ² is a hydrogen atom, Y ³ is —OR ⁷ [wherein R ⁷ represents C ₁ -C ₄ haloalkyl. ], -C (R ⁸ ) = NOR ⁹ [wherein R ⁸ represents a hydrogen atom or methyl, and R ⁹ represents methyl or ethyl. ] And D-7 [wherein Z represents a halogen atom or trifluoromethyl, and n represents 0 or 1. And Y ⁴ is a hydrogen atom.

Y-III: Y ¹ is methyl, Y ² is a hydrogen atom, Y ³ is a halogen atom and trifluoromethyl, and Y ⁴ is a hydrogen atom.

Y-IV: Y ¹ is a halogen atom, Y ² is a halogen atom, C ₁ -C ₃ alkoxy and methylthio, Y ³ is a halogen atom, and Y ⁴ is a hydrogen atom.

YV: Y ¹ is a halogen atom, Y ² is a hydrogen atom, and Y ³ and Y ⁴ are each independently a halogen atom.

Among these, YI, Y-II, Y-IV and YV are more preferable as a combination of substituents represented by Y ¹ , Y ² , Y ³ and Y ⁴ , and YI, Y-IV and YV are more preferable. Particularly preferred.

  In the compounds included in the present invention, examples of the substituent represented by W include an oxygen atom or a sulfur atom, and W is more preferably an oxygen atom.

In the compounds included in the present invention, examples of combinations of preferable ranges of the substituents represented by R ¹ and R ² include the following groups of RI to R-XIX.

That is, RI: R ¹ and R ² are hydrogen atoms.

R-II: ^one of R ¹ and R ² is a halogen atom, and the other is a hydrogen atom.

R-III: ^one of R ¹ and R ² is methyl and the other is a hydrogen atom.

R-IV: One of R ¹ and R ² is methoxy and the other is a hydrogen atom.

RV: R ¹ and R ² are each independently a halogen atom.

R-VI: One of R ¹ and R ² is C ₂ -C ₄ alkyl, and the other is a hydrogen atom.

R-VII: One of R ¹ and R ² is C ₁ -C ₄ haloalkyl, and the other is a hydrogen atom.

R-VIII: One of R ¹ and R ² is C _{2 to} C ₄ alkoxy, and the other is a hydrogen atom.

Of these, RI to R-IVI are more preferable as a combination of the ranges of substituents represented by R ¹ and R ² , and RI to R-III are particularly preferable.

In the compounds included in the present invention, examples of the preferred range of the substituent represented by R ³ include the following groups.

That is, R ³ -I: a hydrogen atom.

R ³ -II: methyl.

R ³ -III: C ₂ -C ₄ alkyl and C ₁ -C ₄ haloalkyl.

Of these, more preferable R ³ -I and R ³ -II as range of the substituent of R ^3, furthermore, R ³ -I is particularly preferred.

In the compounds included in the present invention, examples of the preferred range of the substituent represented by R ⁴ include the following groups.

That is, R ⁴ -I: a hydrogen atom.

R ⁴ -II: methyl.

Among them, as the range of the substituent of R ⁴ R ⁴ -I is particularly preferred.

In the compounds included in the present invention, examples of the preferred range of the substituent represented by R ⁵ include the following groups.

That is, R ⁵ -I: a hydrogen atom.

R ⁵ -II: cyclopropyl.

R ⁵ -III: Methoxy.

Among them, as the range of the substituent of R ^5, more preferably R ⁵ -I and R ⁵ -II, further, R ⁵ -I is particularly preferred.

  Each group which shows the preferable range of each substituent in these compounds included in this invention can be combined arbitrarily, respectively, Each represents the preferable range of this invention compound.

Preferred combinations of ranges for G ¹ , Y ^{1 to} Y ⁴ (indicated by YI to YV), R ¹ and R ² (indicated by RI to R-VIII) and R ⁵ of the compound represented by formula (I) Examples include the combinations shown in Table 1 below. However, the combinations in Table 1 are for illustration, and the compounds of the present invention represented by the formula (I) are not limited to these.
Table 1 Table 1 (continued)
―――――――――――――――――― ――――――――――――――――――
^{G 1 R 5 R 1 / R} 2 Y 1 ~Y 4 G 1 R 5 R 1 / R 2 Y 1 ~Y 4
―――――――――――――――――― ――――――――――――――――――
G ¹ -IR ⁵ -I RI YI G ¹ -XI R ⁵ -I R-III Y-II
G ¹ -IR ⁵ -I RI Y-II G ¹ -XI R ⁵ -I R-III Y-IV
G ¹ -IR ⁵ -I RI Y-III G ¹ -XI R ⁵ -I R-IV YI
G ¹ -IR ⁵ -I RI Y-IV G ¹ -XII R ⁵ -I RI YI
G ¹ -IR ⁵ -I RI YV G ¹ -XII R ⁵ -I R-II YI
G ¹ -IR ⁵ -I R-II YI G ¹ -XII R ⁵ -I R-III YI
G ¹ -IR ⁵ -I R-II Y-II G ¹ -XII R ⁵ -I R-IV YI
G ¹ -IR ⁵ -I R-II Y-IV G ¹ -XIII R ⁵ -I RI YI
G ¹ -IR ⁵ -I R-III YI G ¹ -XIII R ⁵ -I R-II YI
G ¹ -IR ⁵ -I R-III Y-II G ¹ -XIII R ⁵ -I R-III YI
G ¹ -IR ⁵ -I R-III Y-IV G ¹ -XIII R ⁵ -I R-IV YI
G ¹ -IR ⁵ -I R-IV YI G ¹ -XIV R ⁵ -I RI YI
G ¹ -II R ⁵ -I RI YI G ¹ -XIV R ⁵ -I RI Y-II
G ¹ -II R ⁵ -I RI Y-II G ¹ -XIV R ⁵ -I RI Y-IV
G ¹ -II R ⁵ -I RI Y-III G ¹ -XIV R ⁵ -I R-II YI
G ¹ -II R ⁵ -I RI Y-IV G ¹ -XIV R ⁵ -I R-II Y-II
G ¹ -II R ⁵ -I RI YV G ¹ -XIV R ⁵ -I R-II Y-IV
G ¹ -II R ⁵ -I R-II YI G ¹ -XIV R ⁵ -I R-III YI
G ¹ -II R ⁵ -I R-II Y-II G ¹ -XIV R ⁵ -I R-III Y-II
G ¹ -II R ⁵ -I R-II Y-IV G ¹ -XIV R ⁵ -I R-III Y-IV
G ¹ -II R ⁵ -I R-III YI G ¹ -XIV R ⁵ -I R-IV YI
G ¹ -II R ⁵ -I R-III Y-II G ¹ -XV R ⁵ -I RI YI
G ¹ -II R ⁵ -I R-III Y-IV G ¹ -XV R ⁵ -I RI Y-II
G ¹ -II R ⁵ -I R-IV YI G ¹ -XV R ⁵ -I RI Y-IV
G ¹ -III R ⁵ -I RI YI G ¹ -XV R ⁵ -I R-II YI
G ¹ -III R ⁵ -I RI Y-II G ¹ -XV R ⁵ -I R-II Y-II
G ¹ -III R ⁵ -I RI Y-III G ¹ -XV R ⁵ -I R-II Y-IV
G ¹ -III R ⁵ -I RI Y-IV G ¹ -XV R ⁵ -I R-III YI
G ¹ -III R ⁵ -I RI YV G ¹ -XV R ⁵ -I R-III Y-II
G ¹ -III R ⁵ -I R-II YI G ¹ -XV R ⁵ -I R-III Y-IV
G ¹ -III R ⁵ -I R-II Y-II G ¹ -XV R ⁵ -I R-IV YI
^{G 1 -III R 5 -I R-} II Y-IV G 1 -XVI R 5 -I RI YI
^{G 1 -III R 5 -I R-} III YI G 1 -XVI R 5 -I R-II YI
^{G 1 -III R 5 -I R-} III Y-II G 1 -XVI R 5 -I R-III YI
^{G 1 -III R 5 -I R-} III Y-IV G 1 -XVI R 5 -I R-IV YI
^{G 1 -III R 5 -I R-} IV YI G 1 -XVII R 5 -I RI YI
G ¹ -IV R ⁵ -I RI YI G ¹ -XVII R ⁵ -I RI Y-II
G ¹ -IV R ⁵ -I R-II YI G ¹ -XVII R ⁵ -I RI Y-IV
G ¹ -IV R ⁵ -I R-III YI G ¹ -XVII R ⁵ -I R-II YI
G ¹ -IV R ⁵ -I R-IV YI G ¹ -XVII R ⁵ -I R-II Y-II
G ¹ -VR ⁵ -I RI YI G ¹ -XVII R ⁵ -I R-II Y-IV
G ¹ -VR ⁵ -II RI YI G ¹ -XVII R ⁵ -I R-III YI
G ¹ -VR ⁵ -I RI Y-II G ¹ -XVII R ⁵ -I R-III Y-II
G ¹ -VR ⁵ -I RI Y-III G ¹ -XVII R ⁵ -I R-III Y-IV
G ¹ -VR ⁵ -I RI Y-IV G ¹ -XVII R ⁵ -I R-IV YI
G ¹ -VR ⁵ -I RI YV G ¹ -XVIII R ⁵ -I RI YI
G ¹ -VR ⁵ -I R-II YI G ¹ -XVIII R ⁵ -II RI YI
G ¹ -VR ⁵ -II R-II YI G ¹ -XVIII R ⁵ -I RI Y-II
G ¹ -VR ⁵ -I R-II Y-II G ¹ -XVIII R ⁵ -I RI Y-IV
G ¹ -VR ⁵ -I R-II Y-IV G ¹ -XVIII R ⁵ -I R-II YI
G ¹ -VR ⁵ -I R-III YI G ¹ -XVIII R ⁵ -II R-II YI
G ¹ -VR ⁵ -II R-III YI G ¹ -XVIII R ⁵ -I R-II Y-II
G ¹ -VR ⁵ -I R-III Y-II G ¹ -XVIII R ⁵ -I R-II Y-IV
G ¹ -VR ⁵ -I R-III Y-IV G ¹ -XVIII R ⁵ -I R-III YI
G ¹ -VR ⁵ -I R-IV YI G ¹ -XVIII R ⁵ -II R-III YI
G ¹ -VI R ⁵ -I RI YI G ¹ -XVIII R ⁵ -I R-III Y-II
G ¹ -VI R ⁵ -I RI Y-II G ¹ -XVIII R ⁵ -I R-III Y-IV
G ¹ -VI R ⁵ -I RI Y-III G ¹ -XVIII R ⁵ -I R-IV YI
G ¹ -VI R ⁵ -I RI Y-IV G ¹ -XIX R ⁵ -I RI YI
G ¹ -VI R ⁵ -I RI YV G ¹ -XIX R ⁵ -II RI YI
G ¹ -VI R ⁵ -I R-II YI G ¹ -XIX R ⁵ -III RI YI
G ¹ -VI R ⁵ -I R-II Y-II G ¹ -XIX R ⁵ -I RI Y-II
G ¹ -VI R ⁵ -I R-II Y-IV G ¹ -XIX R ⁵ -II RI Y-II
G ¹ -VI R ⁵ -I R-III YI G ¹ -XIX R ⁵ -III RI Y-II
G ¹ -VI R ⁵ -I R-III Y-II G ¹ -XIX R ⁵ -I RI Y-III
G ¹ -VI R ⁵ -I R-III Y-IV G ¹ -XIX R ⁵ -I RI Y-IV
G ¹ -VI R ⁵ -I R-IV YI G ¹ -XIX R ⁵ -II RI Y-IV
G ¹ -VII R ⁵ -I RI YI G ¹ -XIX R ⁵ -III RI Y-IV
G ¹ -VII R ⁵ -I RI Y-II G ¹ -XIX R ⁵ -I RI YV
G ¹ -VII R ⁵ -I RI Y-IV G ¹ -XIX R ⁵ -I R-II YI
^{G 1 -VII R 5 -I R-} II YI G 1 -XIX R 5 -II R-II YI
G ¹ -VII R ⁵ -I R-II Y-II G ¹ -XIX R ⁵ -III R-II YI
G ¹ -VII R ⁵ -I R-II Y-IV G ¹ -XIX R ⁵ -I R-II Y-II
G ¹ -VII R ⁵ -I R-III YI G ¹ -XIX R ⁵ -II R-II Y-II
G ¹ -VII R ⁵ -I R-III Y-II G ¹ -XIX R ⁵ -III R-II Y-II
G ¹ -VII R ⁵ -I R-III Y-IV G ¹ -XIX R ⁵ -I R-II Y-IV
G ¹ -VII R ⁵ -I R-IV YI G ¹ -XIX R ⁵ -II R-II Y-IV
G ¹ -VIII R ⁵ -I RI YI G ¹ -XIX R ⁵ -III R-II Y-IV
G ¹ -VIII R ⁵ -I R-II YI G ¹ -XIX R ⁵ -I R-III YI
G ¹ -VIII R ⁵ -I R-III YI G ¹ -XIX R ⁵ -II R-III YI
G ¹ -VIII R ⁵ -I R-IV YI G ¹ -XIX R ⁵ -III R-III YI
G ¹ -IX R ⁵ -I RI YI G ¹ -XIX R ⁵ -I R-III Y-II
G ¹ -IX R ⁵ -I RI Y-II G ¹ -XIX R ⁵ -II R-III Y-II
G ¹ -IX R ⁵ -I RI Y-IV G ¹ -XIX R ⁵ -III R-III Y-II
G ¹ -IX R ⁵ -I R-II YI G ¹ -XIX R ⁵ -I R-III Y-IV
G ¹ -IX R ⁵ -I R-II Y-II G ¹ -XIX R ⁵ -II R-III Y-IV
G ¹ -IX R ⁵ -I R-II Y-IV G ¹ -XIX R ⁵ -III R-III Y-IV
G ¹ -IX R ⁵ -I R-III YI G ¹ -XIX R ⁵ -I R-IV YI
G ¹ -IX R ⁵ -I R-III Y-II G ¹ -XX R ⁵ -I RI YI
G ¹ -IX R ⁵ -I R-III Y-IV G ¹ -XX R ⁵ -I R-II YI
G ¹ -IX R ⁵ -I R-IV YI G ¹ -XX R ⁵ -I R-III YI
G ¹ -XR ⁵ -I RI YI G ¹ -XX R ⁵ -I R-IV YI
G ¹ -XR ⁵ -I R-II YI G ¹ -XXI R ⁵ -I RI YI
G ¹ -XR ⁵ -I R-III YI G ¹ -XXI R ⁵ -I R-II YI
G ¹ -XR ⁵ -I R-IV YI G ¹ -XXI R ⁵ -I R-III YI
G ¹ -XI R ⁵ -I RI YI G ¹ -XXI R ⁵ -I R-IV YI
G ¹ -XI R ⁵ -I RI Y-II G ¹ -XXII R ⁵ -I RI YI
G ¹ -XI R ⁵ -I RI Y-III G ¹ -XXII R ⁵ -I R-II YI
G ¹ -XI R ⁵ -I RI Y-IV G ¹ -XXII R ⁵ -I R-III YI
G ¹ -XI R ⁵ -I RI YV G ¹ -XXII R ⁵ -I R-IV YI
G ¹ -XI R ⁵ -I R-II YI G ¹ -XXIII R ⁵ -I RI YI
G ¹ -XI R ⁵ -I R-II Y-II G ¹ -XXIII R ⁵ -I R-II YI
G ¹ -XI R ⁵ -I R-II Y-IV G ¹ -XXIII R ⁵ -I R-III YI
G ¹ -XI R ⁵ -I R-III YI G ¹ -XXIII R ⁵ -I R-IV YI
―――――――――――――――――― ――――――――――――――――――
Among the compounds represented by the formula (I) included in the present invention, those that can be converted into acid addition salts according to a conventional method are, for example, hydrofluoric acid, hydrochloric acid, hydrobromic acid, hydrogen iodide. Hydrohalic acid salts such as acids, inorganic acid salts such as nitric acid, sulfuric acid, phosphoric acid, chloric acid, perchloric acid, methanesulfonic acid, ethanesulfonic acid, trifluoromethanesulfonic acid, benzenesulfonic acid, p-toluenesulfone Salts of sulfonic acids such as acids, formic acid, acetic acid, propionic acid, trifluoroacetic acid, fumaric acid, tartaric acid, succinic acid, maleic acid, malic acid, succinic acid, benzoic acid, mandelic acid, ascorbic acid, lactic acid, gluconic acid, citric acid A salt of a carboxylic acid such as an acid or a salt of an amino acid such as glutamic acid or aspartic acid can be used.

  Alternatively, among the compounds represented by the formula (I) included in the present invention, those that can be converted into a metal salt according to a conventional method are, for example, alkali metal salts such as lithium, sodium, and potassium, calcium, and barium. , An alkaline earth metal salt such as magnesium, or an aluminum salt.

  As used herein, the term “pest control agent” means a fungicide and a parasite control agent that are intended to control harmful pathogens and parasites that infect or infest plants or animals. It means fungicides and nematicides in the field of horticulture, or animal antifungal agents and endoparasite control agents.

  As used herein, the term “pathogenic bacteria” means microorganisms that cause plant diseases and animal infectious diseases. Specific examples include the following microorganisms, but specific examples of microorganisms are not limited to these. It is not something.

  Taphrina spp. (Eg Taphrina deformans, T. pruni etc.), Pneumocystis spp., Geotrichum spp., Candida spp. (Eg Candida albicans, C. sorbosa etc.), Pichia spp. (Eg Pichia kluyveri etc.), Capnodium spp. Fumago spp., Hypocapnodium spp., Cercospora spp. (Eg Cercospora apii, C. asparagi, C. beticola, C. capsici, C. carotae, C. kaki, C. kikuchii, C. zonata, etc.), Cercosporidium spp., Cladosporium spp. (Eg Cladosporium colocasiae, C. cucumerinum, C. variabile etc.), Davidiella spp., Didymosporium spp., Heterosporium spp. (Eg Heterosporium allii etc.), Mycosphaerella spr. cerasella, M. fijiensis, M. fragariae, M. graminicola, M. nawae, M. pinodes, M. pomi, M. zingiberis, etc., Mycovellosiella spp. (eg, Mycovellosiella fulva, M. nattrassii, etc.), Paracercospora spp. For example, Paracercospora egenula), Phaeoisariopsis spp., Phaeoramularia spp., Pseudocer cospora spp. (eg Pseudocercospora abelmoschi, P. fuligena, P. vitis etc.), Pseudocercosporella spp. (eg Pseudocercosporella capsellae etc.), Ramichloridium spp., Ramularia spp., Septogloeum spp., Septoria spp. (eg Septoria spp. apiicola, S. chrysanthemella, S. helianthi, S. obesa, etc.), Sphaerulina spp., Aureobasidium spp., Kabatiella spp., Plowrightia spp., Stigmina spp., Elsinoe spp. (eg Elsinoe ampelina, E. araliae, E. fawcettii etc.), Sphaceloma spp. (eg Sphaceloma caricae etc.), Ascochyta spp. (eg Ascochyta pisi etc.), Corynespora spp. (eg Corynespora cassiicola et al.), Leptosphaeria spp. (eg Leptosphaeria coniothyrium, L. ., Phaeosphaeria spp., Ophiosphaerella spp., Setophoma spp., Helminthosporium spp., Alternaria spp. (E.g. Alternaria alternata, A. brassicae, A. brassicicola, A. citri, A. dauci, A. helianthi, A. japonica, A. kikuchiana, A mali, A. panax, A. porri, A. radicina, A. solani etc.), Bipolaris spp. (eg Bipolaris sorghicola etc.), Cochliobolus spp. (eg Cochliobolus heterostrophus, C. lunatus, C. miyabeanus etc.), Curvularia spp. (eg Curvularia geniculata, C. verruculosa etc.), Drechslera spp., Pleospora spp. (eg Pleospora herbarum etc.), Pyrenophora spp. (eg Pyrenophora graminea, P. teres etc.), Setosphaeria spp. (eg Setosphaeria turica etc.) Stemphylium spp. (Eg, Stemphylium botryosum, S. lycopersici, S. solani, S. vesicarium, etc.), Fusicladium spp., Venturia spp. (Eg, Venturia carpophila, V. Inaequalis, V. nashicola, V. pirina, etc.), Didymella spp. (eg Didymella bryoniae, D. fabae etc.), Hendersonia spp., Phoma spp. (eg Phoma erratica var. mikan, P. exigua var. exigua, P. wasabiae etc.), Pyrenochaeta spp. (eg Pyrenochaeta lycopersici etc.) , Stagonospora spp. (Eg Stagonospora sacchari), B otryosphaeria spp. (eg Botryosphaeria berengeriana f. sp. piricola, B. dothidea, etc.), Dothiorella spp., Fusicoccum spp., Guignardia spp., Lasiodiplodia spp. (eg Lasiodiplodia theobromae, etc.), Macrophoma spp. spp., Phyllosticta spp. (eg, Phyllosticta zingiberis), Schizothyrium spp. (eg, Schizothyrium pomi), Acrospermum spp., Leptosphaerulina spp., Aspergillus spp., Penicillium spp. (eg, Penicillium digitum, P. italicumigen, P. italicumigen Etc.), Microsporum spp., Trichophyton spp. (Eg Trichophyton mentagrophytes, T. rubrum etc.), Histoplasma spp., Blumeria spp. (Eg Blumeria graminis f. Sp. Hordei, B. gf sp. Tritici etc.), Erysiphe spp. (Eg, Erysiphe betae, E. cichoracearum, E. c. Var. Cichoracearum, E. heraclei, E. pisi, etc.), Golovinomyces spp. (Eg, Golovinomyces cichoracearum var. Latisporus, etc.), Leveillula spp. (Eg, Leveillula taurica, etc.) Microsphaera spp., Oidium spp. (Eg, Oidium neolycopersici), Phyllactinia spp. (Eg, Phyllactinia kakicola, P. mali, P. moricola, etc.), Podosphaera spp. (Eg, Podosphaera fusca, P. leucotricha, P. pannosa, P. pannosa, P. tridactyla var. tridactyla, P. xanthii, etc.), Sphaerotheca spp. (eg, Sphaerotheca aphanis var. aphanis, S. fuliginea, etc.), Uncinula spp. (eg, Uncinula necator, U. n. var. necator, etc.), Uncinuliella spp. For example, Uncinuliella simulans var. Simulans, U. s. Var. Tandae, etc.), Blumeriella spp. (Eg, Blumeriella jaapii, etc.), Cylindrosporium spp., Diplocarpon spp. (Eg, Diplocarpon mali, D. mespili, D. rosae, etc.), Gloeosporium spp. (eg Gloeosporium minus), Marssonina spp., Tapesia spp. (eg Tapesia acuformis, T. yallundae etc.), Lachnum spp., Scleromitrula spp., Botryotinia spp. (eg Botryotinia fuckeliana etc.), Botrytis spp. (eg Botrytis allii, B. byssoidea, B. cinerea, B. e lliptica, B. fabae, B. squamosa, etc.), Ciborinia spp., Grovesinia spp., Monilia mumecola, Monilinia spp. (eg Monilinia fructicola, M. fructigena, M. laxa, M. mali, M. vaccinii-corymbosi, etc.) , Sclerotinia spp. (Eg, Sclerotinia borealis, S. homoeocarpa, S. minor, S. sclerotiorum, etc.), Valdensia spp. (Eg, Valdensia heterodoxa, etc.), Claviceps spp. (Eg, Claviceps sorghi, C. sorghicola, etc.), Epichloe spp. Ephelis japonica, Villosiclava virens, Hypomyces spp. (Eg Hypomyces solani f. Sp. Mori, H. sf sp. Pisi etc.), Trichoderma spp. (Eg Trichoderma viride etc.), Calonectria spp. (Eg Calonectria ilicispora etc.), Candelo spp., Cylindrocarpon spp., Cylindrocladium spp., Fusarium spp. (eg Fusarium arthrosporioides, F. crookwellense, F. culmorum, F. cuneirostrum, F. oxysporum, F. of sp. adzukicola, F. of sp. allii, F of sp. asparagi, F. of sp. batatas, F. o. f. sp. cepae, F. of s p. colocasiae, F. of sp. conglutinans, F. of sp. cubense, F. of sp. cucumerinum, F. of sp. fabae, F. of sp. fragariae, F. of sp. lactucae, F. of sp lagenariae, F. of sp. lycopersici, F. of sp. melongenae, F. of sp. melonis, F. of sp. nelumbinicola, F. of sp. niveum, F. of sp. radicis-lycopersici, F. of sp. raphani, F. of sp. spinaciae, F. sporotrichioides, F. solani, F. sf sp. cucurbitae, F. sf sp. eumartii, F. sf sp. pisi, F. sf sp. radicicola, etc.), Gibberella spp. (eg Gibberella avenacea, G. baccata, G. fujikuroi, G. zeae, etc.), Haematonectria spp., Nectria spp., Ophionectria spp., Caldariomyces spp., Myrothecium spp., Trichothecium spp., Verticillium spp. Verticillium albo-atrum, V. dahliae, V. longisporum, etc.), Ceratocystis spp. (Eg, Ceratocystis ficicola, C. fimbriata, etc.), Thielaviopsis spp. (Eg, Thielaviopsis basicola, etc.), Adisciso spp., Monochaetia spp., Pestalotia spp. (eg, Pestalotia eriobotrifolia, etc.), Pestalotiopsis spp. (eg, Pestalotiopsis funerea, P. longiseta, P. neglecta, P. theae, etc.), Physalospora spp., Nemania spp., Nodulisporium spp., Roselli (For example, Rosellinia necatrix), Monographella spp. (For example, Monographella nivalis), Ophiostoma spp., Cryphonectria spp. (For example, Cryphonectria parasitica), Diaporthe spp. (For example, Diaporthe citri, D. kyushuensis, D. nomurai, D. tanakae Diaporthopsis spp., Phomopsis spp. (Eg Phomopsis asparagi, P. fukushii, P. obscurans, P. vexans, etc.), Cryptosporella spp., Discula spp. (Eg, Discula theae-sinensis, etc.), Gnomonia spp., Coniella spp., Coryneum spp., Greeneria spp., Melanconis spp., Cytospora spp., Leucostoma spp., Valsa spp. (eg Valsa ceratosperma, etc.), Tubakia spp., Monosporascus spp., Clasterosporium spp., Gaeumannomycesp. Gaeumannomyces graminis etc.), Magn aporthe spp. (eg Magnaporthe grisea etc.), Pyricularia spp. (eg Pyricularia zingiberis etc.), Monilochaetes infuscans, Colletotrichum spp. (eg Colletotrichum acutatum, C. capsici, C. cereale, C. destructivum, C. fragariae, th. , C. nigrum, C. orbiculare, C. spinaciae etc.), Glomerella spp. (Eg Glomerella cingulata etc.), Khuskia oryzae, Phyllachora spp. (Eg Phyllachora pomigena etc.), Ellisembia spp., Briosia spp., Cephalosporium sp. (E.g., Cephalosporium gramineum), Epicocumcum spp., Gloeocercospora sorghi, Mycocentrospora spp., Peltaster spp. (E.g., Peltaster fructicola), Phaeocytostroma spp., Phialophora spp. (E.g. Ascomycota fungi such as Rhynchosporium secalis (eg, Rhynchosporium secalis), Sarocladium spp., Coleophoma spp., Helicoceras oryzae.

  Septobasidium spp. (Eg, Septobasidium bogoriense, S. tanakae, etc.), Helicobasidium spp. (Eg, Helicobasidium longisporum, etc.), Coleosporium spp. (Eg, Coleosporium plectranthi, etc.), Cronartium spp., Phakopsora spp. (Eg, Phakopsora artemisia P. pachyrhizi etc.), Physopella spp. (Eg Physopella ampelopsidis etc.), Kuehneola spp. (Eg Kuehneola japonica etc.), Phragmidium spp. (Eg Phragmidium fusiforme, P. mucronatum, P. rosae-multiflorae etc.), Gymnosporangium spp. For example, Gymnosporangium asiaticum, G. yamadae, etc.), Puccinia spp. (Eg Puccinia allii, P. brachypodii var. Poae-nemoralis, P. coronata, P. c. Var. Coronata, P. cynodontis, P. graminis, P. g subsp. graminicola, P. hordei, P. horiana, P. kuehnii, P. melanocephala, P. recondita, P. striiformis var. striiformis, P. tanaceti var. tanaceti, P. tokyensis, P. zoysiae), Uromyces spp. (eg Uromyces phaseoli var. azukicola, U. p. var. phaseoli, Uromyces viciae-fabae var. viciae-fabae etc.), Naohidemyces vaccinii, Nyssopsora spp., Leucotelium spp., Tranzschelia spp. Etc.), Uredo spp., Sphacelotheca spp., Urocystis spp., Sporisorium spp. (Eg Sporisorium scitamineum etc.), Ustilago spp. (Eg Ustilago maydis, U. nuda etc.), Entyloma spp., Exobasidium rep. E. vexans etc.), Microstroma spp., Tilletia spp. (Eg Tilletia caries, T. controversa, T. laevis etc.), Itersonilia spp. (Eg Itersonilia perplexans etc.), Cryptococcus spp., Bovista spp. (Eg Bovista dermoxantha) Etc.), Lycoperdon spp. (Eg Lycoperdon curtisii, L. perlatum etc.), Conocybe spp. (Eg Conocybe apala etc.), Marasmius spp. (Eg Marasmius oreades etc.), Armillaria spp., Helotium spp., Lepista spp. (Eg Lepista subnuda, etc.), Sc lerotium spp. (eg Sclerotium cepivorum), Typhula spp. (eg Typhula incarnata, T. ishikariensis var. ishikariensis etc.), Athelia spp. (eg Athelia rolfsii etc.), Ceratobasidium spp. (eg Ceratobasidium cornigehiza sp. Rhizoctonia spp. (For example, Rhizoctonia solani), Thanatephorus spp. (For example, Thanatephorus cucumeris), Laetisaria spp., Waitea spp., Fomitiporia spp., Ganoderma spp., Chondostereum purpureum, Phanerochaete spp. ) Fungi.

  Chipidiomycota fungi such as Olpidium spp.

  Blastocladiomycota fungi such as Physoderma spp.

  Choanephora spp., Choanephoroidea cucurbitae, Mucor spp. (Eg Mucor fragilis), Rhizopus spp. (Eg Rhizopus arrhizus, R. chinensis, R. oryzae, R. stolonifer var. Stolonifer), etc. .

  Cercozoa protists such as Plasmodiophora spp. (Eg, Plasmodiophora brassicae), Spongospora subterranea f. Sp. Subterranea, etc.

  Aphanomyces spp. (Eg Aphanomyces cochlioides, A. raphani etc.), Albugo spp. (Eg Albugo macrospora, A. wasabiae etc.), Bremia spp. (Eg Bremia lactucae etc.), Hyaloperonospora spp., Peronosclerospora spp., Peronospora spp. For example, Peronospora alliariae-wasabi, P. chrysanthemi-coronarii, P. destructor, P. farinosa f. Sp. Spinaciae, P. manshurica, P. parasitica, P. sparsa, etc., Plasmopara spp. (Eg Plasmopara halstedii, P. nivea) , P. viticola, etc.), Pseudoperonospora spp. (Eg, Pseudoperonospora cubensis, etc.), Sclerophthora spp., Phytophthora spp. infestans, P. melonis, P. nicotianae, P. palmivora, P. porri, P. sojae, P. syringae, P. vignae f. sp. adzukicola, etc.), Pythium spp. (eg Pythium afertile, P. aphanidermatum, P. apleroticum, P. aristosporum, P. arrhenomanes, P. buismaniae, P. debaryanum, P. gr aminicola, P. horinouchiense, P. irregulare, P. iwayamai, P. myriotylum, P. okanoganense, P. paddicum, P. paroecandrum, P. periplocum, P. spinosum, P. sulcatum, P. sylvaticum, P. ultimum var ultimum, P. vanterpoolii, P. vexans, P. volutum, etc.), etc. (Heterokontophyta) oomycetes (Oomycetes).

  Actinobacter gram-positive bacteria such as Clavibacter spp. (Eg Clavibacter michiganensis subsp. Michiganensis), Curtobacterium spp., Leifsonia spp. (Eg Leifsonia xyli subsp. Xyli etc.), Streptomyces spp. (Eg Streptomyces ipomoeae etc.) .

  Firmicutes gram-positive fungi such as Clostridium sp.

  Tenericutes gram-positive fungi such as Phytoplasma.

  Rhizobium spp. (Eg Rhizobium radiobacter), Acetobacter spp., Burkholderia spp. (Eg Burkholderia andropogonis, B. cepacia, B. gladioli, B. glumae, B. plantarii etc.), Acidovorax avenae subsp. Subsp. Citrulli, A. konjaci, etc.), Herbaspirillum spp., Ralstonia spp. (Eg, Ralstonia solanacearum), Xanthomonas spp. (Eg, Xanthomonas albilineans, X. arboricola pv. Pruni, X. axonopodis pv. Vitians) , X. campestris pv. Campestris, X. c. Pv. Cucurbitae, X. c. Pv. Glycines, X. c. Pv. Mangiferaeindicae, X. c. Pv. Nigromaculans, X. c. Pv. Vesicatoria, X. citri subsp. citri, X. oryzae pv. oryzae, etc.), Pseudomonas spp. (eg Pseudomonas cichorii, P. fluorescens, P. marginalis, P. m. pv. marginalis, P. savastanoi pv. glycinea, P. syringae, P s.pv.actinidiae, P.s.pv.eriobotryae, P.s.pv.helianthi, P.s.pv.lachrymans, P.s.pv.maculicola, P.s.pv.mori, P.s pv. morsprunorum, P. p. spinaciae, P. s. pv. syringae, P. s. pv. theae, P. viridiflava, etc., Rhizobacter spp., Brenneria spp. (eg, Brenneria nigrifluens etc.), Dickeya spp. (eg, Dickeya dianthicola, D. zeae etc.), Erwinia spp. (Eg Erwinia amylovora, E. rhapontici etc.), Pantoea spp., Pectobacterium spp. (Eg Pectobacterium atrosepticum, P. carotovorum, P. wasabiae etc.) gram of Proteobacteria gram Negative fungi.

  Specific examples of plant diseases and animal infections caused by infection and growth of these pathogenic bacteria include the following plant diseases and animal infections, but specific examples of plant diseases and animal infections are limited to these. Is not to be done.

Plant diseases:
Leaf curl (Taphrina deformans), Plum pockets (Taphrina pruni), Asparagus brown spot Leaf spot (Cercospora asparagi), sugar beet brown spot Cercospora leaf spot (Cercospora beticola), pepper spot Frogeye leaf spot (Cercospora capsici), oyster horn spot leaf disease Angular leaf spot (Cercospora kaki), soybean purpura purple stain (Cercospora kikuchii), groundnut brown leaf spot (Mycosphaerella arachidis), sweet cherry brown spot disease (Cylindrosporium leaf spot) Mycosphaerella cerasella, Blumeriella jaapii), wheat leaf blight, Speckled leaf blotch (Mycosphaerella graminicola), oyster lobster circular leaf spot (Mycosphaerella nawae), pea brown spot Mycosphaerella blight (Mycosphaerella pinodes), myaf spot Mycosphaerella zingiberis), tomato leaf mold Leaf mold (Mycovellosiella fulva), eggplant soot mold Leaf mold (Mycovellosiella natt rassii), tomato scab fungus Cercospora leaf mold (Pseudocercospora fuligena), grape brown spot Isariopsis leaf spot (Pseudocercospora vitis), Chinese cabbage leaf spot Leaf spot (Pseudocercosporella capsellae), chrysanthemum black spot Leaf spot (Septoria chrysant brown) Leaf blight (Septoria obesa), grape black scab Anthracnose (Elsinoe ampelina), peanut scab Spot anthracnose (Elsinoe araliae), citrus scab Scab (Elsinoe fawcettii), pea brown spot Leaf spot (Ascochyta pisi) , Cucumber brown spot Corynespora leaf spot (Corynespora cassiicola), rose blight Stem canker (Leptosphaeria coniothyrium), rose black spot Leaf spot (Alternaria alternata), carrot black leaf blight Leaf blight (Alternaria dauci), pear black spot Disease Black spot (Alternaria kikuchiana), Apple spot leaf fall Alternaria blotch (Alternaria mali), Green onion black spot Alternaria leaf spot (Alternaria porri), Sorghum Purple spot disease (Bipolaris sorghicola), maize sesame leaf blight Southern leaf blight (Cochliobolus heterostrophus), rice sesame leaf blight Brown spot (Cochliobolus miyabeanus), garlic leaf blight Tip blight (Pleospora herbarum), barley leaf blight Stripe (Pyrenophora graminea), Barley net spot disease Net blotch (Pyrenophora teres), Sorghum soot disease Leaf blight (Setosphaeria turcica), Corn soot disease Northern leaf blight (Setosphaeria turcica), Asparagus spot disease leaf spot (Stemphylium botryosum) Scab (Venturia carpophila), apple scab Scab (Venturia Inaequalis), pear scab Scab (Venturia nashicola), cucurbit vine blight Gummy stem blight (Didymella bryoniae), burdock black spot Disease leaf spot (Phoma exigua var. Exigua), Wasabi ink-filled disease Streak (Phoma wasabiae), Ring rot (Botryosphaeria berengeriana f. Sp.) piricola), soft rot (Botryosphaeria dothidea, Lasiodiplodia theobromae, Diaporthe sp.), citrus green mold (Penicillium digitatum), citrus blue mold (Penicillium italicum), barley powdery mildew Powdery mildew (Blumeria graminis f. sp. hordei), wheat powdery mildew Powdery mildew (Blumeria graminis f. sp. tritici), cucumber powdery mildew Powdery mildew (Erysiphe betae, Leveillula taurica, Oidium sp., Podosphaera xanthii), eggplant udon Powdery mildew (Erysiphe cichoracearum, Leveillula taurica, Sphaerotheca fuliginea), carrots, parsley powdery mildew Powdery mildew (Erysiphe heraclei), pea powdery powdery mildew (Erysiphe pisi), tomato powdery mildew Poillery mildew Oidium neolycopersici, Oidium sp.), Pepper powdery mildew (Leveillula taurica), pumpkin powdery powdery mildew (Oidium sp., Podosphaera xanthii), powdery mildew (Oidium sp.), oyster powdery mildew Powdery mildew (Phyllactinia kakicola), burdock powdery mildew (Podosphaera fusca), apple powdery mildew (Podosphaera leucotricha), powdery mildew (Podosphaera pannosa, Uncinuliella simulans var. Simulans, U. s. Var. Tandae), powdery mildew (podosphaera xanthii), strawberry wdery mildew (Sphaerotheca aphanis var. Aphanis), watermelon, melon powdery mildew (Sphaerotheca fuliginea), grape powdery mildew (Uncinula necator, U. n. Var. Necator), apple brown spot Blotch (Diplocarpon mali) Black spot (Diplocarpon rosae), onion gray rot, Gray mold neck rot (Botrytis allii), gray mold, Botrytis blight (Botrytis cinerea), Leaf blight (Botrytis cinerea, B. byssoidea, B. squamosa), Chocolate spot (Botrytis cinerea, B. elliptica, B. fabae), Brown rot (Monilinia fructicola) , M. fructigena, M. laxa), apple moniliosis Blossom blight (Monilinia mali), Shivadara spot disease, Dollar spot (Sclerotinia homoeocarpa), mycorrhizal disease Cottony rot, Sclerotinia rot, Stem rot (Sclerotinia sclerotiorum), rice koji False smut (Villosiclava virens), soybean black root rot Root necrosis (Calonectria ilicicola), wheat red mold Fusarium blight (Fusarium crookwellense, F. culmorum, Gibberella avenacea, G. zeae, Monographella nivalis), barley red mold blight Fus Fusarium culmorum, Gibberella avenacea, G. zeae), dry rot of konjac Dry rot (Fusarium oxysporum, F. solani f. Sp. Radicicola), brown rot (Fusarium oxysporum, F. solani f. Sp. Pisi, F. sf sp. radicicola), Fusarium wilt (Fusarium oxysporum f. sp. adzukicola), dry rot fungus Fusarium basal rot (Fusarium oxysporum f. sp. allii, F. solani f. sp. radicicola), Stem potato (Fusarium oxysporum f. Sp. Batatas, F. solani), dry rot dry rot (Fusarium oxysporum f. Sp. Colocasiae), cabbage, yellow rot of Komatsuna yellow (Fusarium oxysporum f. Sp. Conglutinans), banana panama disease Panama disease (Fusarium oxysporum f. Sp. Cubense), Fusarium wilt (Fusarium oxysporum f. Sp. Fragariae), lettuce root rot (Fusarium oxysporum f. Sp. Lactucae), Fusarium wilt (Fusarium oxysporum f. Fusarium oxysporum f. Sp. Lagenariae, F. of sp. Niveum), tomato wilt Fusarium wilt (Fusarium oxysporum f. Sp. Lycopersici), melon vine split Fusarium wilt (Fusarium oxysporum f. Sp. Melonis) Yellows (Fusarium oxysporum f. Sp. Raphani), Fusarium wilt (Fusarium oxysporum f. Sp. Spinaciae), rice seedling disease “Bakanae” disease (Gibberella fujikuroi), Verticillium black spot (Verticillium albo-atrum, V. dahliae), tomato, Eggplant, half body wilt disease of Verticillium wilt (Verticillium dahliae), fig strain blight Ceratocystis canker (Ceratocystis ficicola), black rot (Ceratocystis fimbriata), tea ring spot gray blight (Pestalotiopsis longiseta, P. , Chestnut blight Endothia canker (Cryphonectria parasitica), citrus black spot Melanose (Diaporthe citri), asparagus stem blight Stem blight (Phomopsis asparagi), pear blight Phomopsis canker (Phomopsis fukushii), eggplant brown spot disease Brown spot (Phomopsis vexans), tea anthracnose Anthracnose (Discula theae-sinensis), apple rot Valsa canker (Valsa ceratosperma), rice blast Blast (Magnaporthe g) risea), strawberry anthracnose Crown rot (Colletotrichum acutatum, C. fragariae, Glomerella cingulata), apple anthracnose Bitter rot (Colletotrichum acutatum, Glomerella cingulata), sweet potato anthracnose (Colletotrichum acutatum, Glomerella raculose moss) Colletotrichum acutatum), Grape late rot Ripe rot (Colletotrichum acutatum, Glomerella cingulata), Sengiku anthracnose Anthracnose (Colletotrichum acutatum), Anthracnose anthracnose (Colletotrichum lindemuthianum) Anthracnose (Glomerella cingulata), chestnut anthracnose Anthracnose (Glomerella cingulata), oyster anthracnose Anthracnose (Glomerella cingulata), azuki bean leaf rot Brown stem rot (Phialophora gregata) (Rhynchosporium secalis),
Fig Rust (Phakopsora nishidana), Soybean Rust (Phakopsora pachyrhizi), Rose Rust (Kuehneola japonica, Phragmidium fusiforme, P. mucronatum, P. rosae-multiflorae), Pear Red Rust (Gymnosporangium), Gymnosporangium Red Star Rust (Gymnosporangium yamadae), Rust of Rubiaceae Rust (Puccinia allii), Chrysanthemum White Rust (Puccinia horiana), Wheat Red Rust Brown rust (Puccinia recondita), Chrysanthemum Rust (Puccinia tanaceti var. Tanaceti) ), Broad bean rust Rust (Uromyces viciae-fabae var. Viciae-fabae), sugarcane smut Smut (Sporisorium scitamineum), corn smut Smut (Ustilago maydis), barley naked smut (Ustilago nuda), tea net rice cake Diseases Net blister blight (Exobasidium reticulatum), tea blast Blister blight (Exobasidium vexans), white silkworm Stem rot, Southern blight (Athelia rolfsii), chrysanthemum Root and stem rot (Cera) tobasidium cornigerum, Rhizoctonia solani), Rhizoctonia solani, cabbage seedling blight Damping-off (Rhizoctonia solani), bee blight Damping-off (Rhizoctonia solani), lettuce blight disease Bottom rot (Rhizoctonia ), Brown leaf rot, brown patch, large patch (Rhizoctonia solani), rice blight disease, Sheath blight (Thanatephorus cucumeris), sugar beet root rot, leaf blight (Thanatephorus cucumeris),
Rhizopus rot (Rhizopus stolonifer var. Stolonifer),
Clubroot (Plasmodiophora brassicae),
Sugar beet root disease Aphanomyces root rot (Aphanomyces cochlioides), white rust (Albugo macrospora) of Brassicaceae, lettuce downy mildew (Bremia lactucae), downy mildew (Peronospora chrysanthemi-coronarii), onion, Downy mildew (Peronospora destructor), spinach downy mildew (Peronospora farinosa f. Sp. Spinaciae), downy mildew (Peronospora manshurica), downy mildew (Peronospora parasitica) ), Downy mildew (Peronospora sparsa), downy mildew (Plasmopara halstedii), downy mildew (Plasmopara nivea), downy mildew (Plasmopara viticola), downy mildew And Downy mildew (Pseudoperonospora cubensis), Phylophthora root rot (Phytophthora cactorum), watermelon brown rot (Phytophthora capsici), Phytophthora rot (Phytophthora capsici), Pepper plague Phytophthora blight (Phytophthora capsici), Watermelon plague Phytophthora rot (Phytophthora cryptogea), Tomato, Potato plague Late blight (Phytophthora infestans) Leaf blight (Phytophthora porri), soybean stem plague Phytophthora root and stem rot (Phytophthora sojae), azuki bean stem disease Phytophthora stem rot (Phytophthora vignae f. Sp. Adzukicola), spinach blight , P. myriotylum, P. paroecandrum, P. ultimum var. Ultimum), konjac root rot Root rot (Pythium aristosporum), corn root rot Browning root rot (Pythium arrhenomanes, P. graminicola), cabbage seedling damping -off (Pythium buismaniae, P. myriotylum), Root rot (Pythium myriotylum), ginger rhizome rot Roo t rot (Pythium myriotylum, P. ultimum var. ultimum), carrot stain rot Brown blotted root rot (Pythium sulcatum),
Tomato Scab Bacterial canker (Clavibacter michiganensis subsp. Michiganensis), Potato Scab Scab (Streptomyces spp.),
Crown gall (Rhizobium radiobacter), sorghum streak bacterial disease Bacterial stripe (Burkholderia andropogonis), onion rot Soft rot (Burkholderia cepacia, Pseudomonas marginalis pv. Marginalis, Erwinia rhapontici), rice Bacterial grain rot (Burkholderia gladioli, B. glumae), Bacterial fruit blotch (Acidovorax avenae subsp. Citrulli), Bacterial leaf blight (Acidovorax konjaci), Bacterial wilt (Ralstonia) ), Bacterial shot hole (Xanthomonas arboricola pv. Pruni, Pseudomonas syringae pv. Syringae, Brenneria nigrifluens), Plum black spot Bacterial leaf spot (Xanthomonas arboricola pv. Pruni), Bacterial apox pv. vitians), cruciferous black rot (Xanthomonas campestris pv. campestris), soybean leaf burning Bacterial pustule (Xanthomonas glycest), burdock black spot Bacterial spot (Xanthomonas campestris pv. nigromaculans), green spot Bacterial spot Bacterial spot (Xanthomonas campestris pv. vesicatoria), Citrus canker (Xanthomonas citri subsp. citri), spring Rot (Pseudomonas cichorii, P. marginalis pv. Marginalis, Erwinia sp.), Lettuce rot Bacterial rot (Pseudomonas cichorii, P. marginalis pv. Marginalis, P. viridiflava), kiwi fruit bacteriomycosis Bacterial blossom blight (Pseudomonmon marginalis pv. marginalis, P. syringae pv. syringae, P. viridiflava), kiwifruit scab Bacterial canker (Pseudomonas syringae pv. actinidiae), loquat cancer canker (Pseudomonas syringae pv. eriobotryae) Bacterial spot (Pseudomonas syringae pv. Lachrymans), Bacterial black spot (Pseudomonas syringae pv. Maculicola), ume Bacterial canker (Pseudomonas syringae pv. Morsprunorum, Erwinia sp.), Tea red burn Bacterial shoot blight (Pseudomonas syringae pv. Theae), leek soft rot Bacterial soft rot (Dickeya sp., Pectobacterium carotovorum), Rosaceae Fire blight (Erwinia amylovora), konjac rot Soft rot (Pectobacterium carotovorum), soft rot Bacterial soft rot (Pectobacterium carotovorum).

Animal infections:
Pneumocystis pneumonia (Pneumocystis jirovecii), Candidiasis (Candida albicans), Aspergillosis (Aspergillus fumigatus), Trichophytosis (Microsporum canis, M. gypseum, T. phytorum. verrucosum), Histoplasmosis (Histoplasma capsulatum), Cryptococcosis (Cryptococcus neoformans).

  In the present specification, the term “parasite” means a plant parasitic linear animal parasitic on a plant, an animal parasitic linear animal parasitic on an animal, a bald animal, a flat animal, a protozoan, and the like. For example, the following parasites can be mentioned, but specific examples of the parasites are not limited to these.

  Giant kidney worm (Dioctophyma renale), ringed capillary worm Thread worms (Capillaria annulata), torsion capillary nematode Cropworm (Capillaria contorta), liver capillary nematode Capillary liver worm (Capillaria hepatica), penetrating capillary nematode (Capillaria) perforans), Philippine Capillaria philippinensis, Capillaria suis, Caterpillar Whipworm (Trichuris discolor), Whipworm Whipworm (Trichuris ovis), Pig whipworm Pig Whipworm (Trichuris suis), human Enoplida nematodes such as the whipworm Human whipworm (Trichuris trichiura), the dog whipworm Dog whipworm (Trichuris vulpis), and the Trichinella pork worm (Trichinella spiralis).

  桿 such as Nipple faecal nematode Intestinal threadworm (Strongyloides papillosus), cat fecal nematode (Strongyloides planiceps), pig fecal nematode Pig threadworm (Strongyloides ransomi), human fecal nematode Threadworm (Strongyloides stercoralis), Micronema spp. Rhabditida nematode.

  Brazilian Hookworm (Ancylostoma braziliense), Dog Hookworm Dog hookworm (Ancylostoma caninum), Zubini Hookworm Old World hookworm (Ancylostoma duodenale), Cat Hookworm Cat hookworm (Ancylostoma tubaeforme), Narrowhead Hookworm The Northern hookworm of dogs (Uncinaria stenocephala) Caterpillar Cattle hookworm (Bunostomum phlebotomum), Sheep worm, Small ruminant hookworm (Bunostomum trigonocephalum), American worm New World hookworm (Necator americanus), Cyathostomum spp., Cylicocyclus spyl. spp.), Cylicostephanus spp., Donkeys (Strongylus asini), edentulous (Strongylus edentatus), Horse worms Blood worm (Strongylus equinus), Common worms Blood worm (Strongylus vulgaris) Large-mouthed bowel worm (Chabertia ovina), Indian nodular worm (Oesophagostomum brevic) audatum), Colombian nodule worm (Oesophagostomum columbianum), Nodule worm (Oesophagostomum dentatum), Nodular worm (Oesophagostomum georgianum), Nodular worm (Oesophagostomum columbianum) Nodular worm (Oesophagostomum quadrispinulatum), cattle intestinal nodular worm (Oesophagostomum radiatum), goat intestinal nodular worm (Oesophagostomum venulosum), scrijabin worm (Syngamus skrjabinomorpha), chicken worm moth trachea (Syngamus skrjabinomorpha) Swine kidney worm (Stephanurus dentatus), Couperia cattle bankrupt worm (Cooperia oncophora), red stomach worm (Hyostrongylus rubidus), stomach hair worm (Trichostrongylus axei), serpentine ciliate nematode (Trichostrongylus colubriformis), Oriental ciliate nematode Oriental trichostrongylus (Trichostrongylus orientalis), torsion stomachworm Red stomach worm (Haemonchus co ntortus), cattle stomach worm (Mecistocirrus digitatus), Ostertag stomach worm (Ostertagia ostertagi), filamentous lungworm Common lungworm (Dictyocaulus filaria), bovine lungworm Bovine lungworm (Dictyocaulus viviparus) Insect worms (Nematodirus filicollis), Swine lungworm (Metastrongylus elongatus), Lungworm (Filaroides hirthi), Lungworm (Crenosoma aerophila), Fox lungworm (Crenosoma vulpis) Strong lungida nematodes such as Rat lung worm (Angiostrongylus cantonensis), Schistosoma nematode French heartworm (Angiostrongylus vasorum), Protostrongylus spp.

  Rice white nematode (Aphelenchoides besseyi), strawberry nematode, Strawberry foliar nematode (Aphelenchoides fragariae), chrysanthemum foliar nematode (Aphelenchoides ritzemabosi), pine wood nematode (Bineurus) Aphelenchida) Nematode.

  Potato cyst nematode (Globodera pallida), Potato cyst nematode (Globodera rostochiensis), Wheat cyst nematode (Heterodera avenae), Soybean cyst nematode cyst nematode (Heterodera schachtii), clover cyst nematode Clover cyst nematode (Heterodera trifolii), arenaria root nematode Peanut root-knot nematode (Meloidogyne arenaria), red root nematode Northern root-knot nematode (Meloidogyne incognita), Java root-knot nematode (Meloidogyne javanica), Apple root-knot nematode (Meloidogyne mali), Southern nematode sale nematode Cof fee root-lesion nematode (Pratylenchus coffeae), sawtooth nematode (Pratylenchus drenatus), chanegusaresenchu Tea root-lesion nematode (Pratylenchus loosi), wheat root nematode California root-lesion nematode (bb) -lesion nematode (Pratylenchus penetrans), Walnut root-lesion nematode (Pratylenchus vulnus), Citrus burrowing nematode (Radopholus citrophilus), Banana burrowing nesimde (Radopholus) (Tylenchida) Nematode.

Oxyurida nematodes such as human worm Pinworm (Enterobius vermicularis), horse worm Equine pinworm (Oxyuris equi), rabbit worm Rabbit pinworm (Passalurus ambiguus),
Pig roundworm (Ascaris suum), Horse roundworm Horse roundworm (Parascaris equorum), Dog roundworm Dog roundworm (Toxascaris leonina), Dog roundworm Dog intestinal roundworm (Toxocara canis), Cat roundworm Feline roundworm (Toxocara cati), Cattle roundworm Large cattle roundworm (Toxocara vitulorum), Anisakis spp., Pseudoterranova spp., chicken caecal caecal worm (Heterakis gallinarum), chicken roundworm (Ascaridia galli) and other roundworms (Ascaridida) Nematode.

  Medinaworm Guinea worm (Dracunculus medinensis), Dolores jaw-and-mouth beetle (Gnathostoma doloresi), Ganthostoma hispidum, Japanese jaw-and-mouth beetle (Gnathostoma nipponicum), Reddish-coloured worm (Gnathostoma spinigerum) Dog stomach worm (Physaloptera canis), cat stomach worm (Physaloptera felidis, P. praeputialis), lala gastroworm Feline / canine stomach worm (Physaloptera rara), oriental eyeworm Eye worm (Thelazia callipaeda), Bovine eyeworm (Thelazia rhodesi), Large mouth stomach worm (Draschia megastoma), Equine stomach worm (Habronema microstoma), Stomach worm (Habronema muscae), Beautiful esophagus Gullet worm ( Gongylonema pulchrum), Thick stomach worm (Ascarops strongylina), Parafilaria (Parafilaria bovicola), Parafilaria multipapillosa, Stephanofilaria okinawaensis), Bancroft filaria (Wuchereria bancrofti), Malay filamentous worm (Brugia malayi), Neck threadworm (Onchocerca cervicalis), Gibson filamentous worm (Onchocerca gibsoni), Cattle filarial worm (Onchocercer gautum) ), Convolvulus (Onchocerca volvulus), finger filamentous worm Bovine filarial worm (Setaria digitata), equine filamentous peritoneal worm (Setaria equina), papillary larva (Setaria labiatopapillosa), marshall filariae (Setaria marshalli), dog Spirurida nematodes such as the filamentous worm Dog heartworm (Dirofilaria immitis) and the Loa filamentous african eye worm (Loa loa).

  Craniopods such as Moniliformis moniliformis and Giant thorny-headed worm (Macracanthorhynchus hirudinaceus).

  Artificial leaves such as Fish tapeworm (Diphyllobothrium latum), Diphyllobothrium nihonkaiense, Manson tapeworm (Spirometra erinaceieuropaei), Diplogonoporus grandis Eye (Pseudophyllidea) tapeworm.

  Wire worms (Mesocestoides lineatus), striped worms Chicken tapeworm (Raillietina cesticillus), spiny cleft worm Fowl tapeworm (Raillietina echinobothrida), square tapeworm Chicken tapeworm (Raillietina tetragona), canine tapeworm (Taenia hydatigena), Canine tapeworm (Taenia multiceps), sheep worm Sheep measles (Taenia ovis), beetle tapeworm Dog tapeworm (Taenia pisiformis), striped beetle Beef tapeworm (Taenia saginata), striped worm Tapeworm (Taenia serialis) ), Rodentworm Pork tapeworm (Taenia solium), caterpillar Feline tapeworm (Taenia taeniaeformis), single tapeworm Hydatid tapeworm (Echinococcus granulosus), multi-budworm, small fox tapeworm (Echinococcus multilocularis), cat (Echinococcus oligarthrus), Vogel's crustacean (Echinococcus vogeli), reduced tapeworm Rat tapeworm (Hymenolepis diminuta), small tapeworm Dwarf tapeworm (Hymenolepis nana), crustacea double-pored dog tapeworm (Dipylidium ca ninum), cuneate tapeworms (Amoebotaenia sphenoides), funnel-like crustaceans (Choanotaenia infundibulum), quail crustaceans (Metroliasthes coturnix), crustacea Equine tapeworm (Anoplocephala magna), phytophyte crustacean Cecal tapeworm (Anoplocephala perfoliata), papillae Cyclophyllidea worms such as insect Dwarf equine tapeworm (Paranoplocephala mamillana), Benedenta worm Common tapeworm (Moniezia benedeni), extended tapeworm Sheep tapeworm (Moniezia expansa), genus Stilesia spp.

  Stripeidida, such as Pharyngostomum cordatum, Blood fluke (Schistosoma haematobium), Blood fluke (Schistosoma japonicum), and Schistosoma mansoni.

  Echinostoma cinetorchis, Echinostoma hortense, Giant liver fluke (Fasciola gigantica), Liver common liver fluke (Fasciola hepatica), Fasciolopsis buski, Flat belly twin Echinostomida flukes such as Homalogaster paloniae.

  Continental flukes (Dicrocoelium chinensis), moth-type flukes Lancet liver fluke (Dicrocoelium dendriticum), African moth-type flukes African lancet fluke (Dicrocoelium hospes), small pancreatic folds (Eurytrema coelomaticum), pancreatic folds Pancreatic fluke (Eurytrema pancreaticum) Plumiorchiida flukes, such as Paragonimus miyazakii, Paragonimus ohirai, Lester fluke (Paragonimus westermani), etc.

  Amphimerus spp., Liver fluke Chinese liver fluke (Clonorchis sinensis), Cat liver fluke Cat liver fluke (Opisthorchis felineus), Thai liver fluke Southeast Aasian liver fluke (Opisthorchis viverrini), Pseudamphistom spp .), Metrochis spp., Parametorchis spp., Malformed fluke (Heterophyes heterophyes), Metagonimus yokokawai, foregut fluke (Pygidiopsis summa), etc. Opisthorchiida).

  Amoeba such as Entamoeba histolytica (E. invadens).

  Futago Babesia (Babesia bigemina), Cattle Babesia bovis, Big Horse Babesia caballi, Dog Babesia canis, Cat Babesia felis, Gibson dog Babesia gibsoni, Large Piroplasma (Babesia ovata) ), Cytauxzoon felis, tropical piroplasmosis Tyleria (Theileria annulata), pseudocoastal fever Tyreria (Theileria mutans), small piroplasma (Theileria orientalis), east coast fever Tyrelia (Theileria parva), etc. Piroplasmida sporozoites.

  Haemoproteus mansoni, chicken leucocytozone (Leucocytozoon caulleryi), Plasmodium falciparum, Plasmodium malariae, Plasmodium ovale, Plasmodium ovale Haemosporida spores such as protozoa (Plasmodium vivax).

  Caryospora spp., Eimeria acervulina, Eimeria bovis, Eimeria brunetti, Eimeria maxima, Eimeria necatrix, Eimeria necatrix Eimeria ovinoidalis, rabbit liver coccidium (Eimeria stiedae), chicken cecal coccidium (Eimeria tenella), dog isospora canis, feline isospora (Isospora felis), porcine isospora suis (Isospora suis), Tizeria aleni , Tyzzeria anseris, Tyzzeria perniciosa, Wenyonella anatis, Wenyonella gagari, Cryptosporidium canis, cat crypt Cryptosporidium felis, Cryptosporidium hominis, turkey Cryptosporidium meleagridis, Cryptosporidium muris, small Cryptosporidium parvco, sarcosis (Sarcocystis cruzi), Sarcocystis felis, Sarcocystis hominis, Sarcocystis miescheriana, Sarcocystis neurona, Sarcocystis colostis tenis S tenis Sarcocystis ovalis), Toxoplasma gondii, dog hepatozoon (Hepatozoon canis), cat hepatozoon (Hepatozoon felis), etc. cidiorida).

  Vestibuliferida ciliates such as large colonic barantidium coli.

  Trichomonadida flagellates such as Histomonas meleagridis, Pentatrichomonas hominis, Trichomonas tenax.

  Diplomonadida flagellates such as Giardia intestinalis, Giardia muris, turkey hexamita (Hexamita meleagridis), Hexamita parva.

  Leishmania donovani, Leishmania infantum, Leishmania major, Leishmania tropica, Trypanosoma brucei gambiense, Trypanosoma brucei cruise, Trypanosoma brucei rhodesi Kinetoplastid flagellates such as Trypanosoma cruzi, Trypanosoma equiperdum, and Trypanosoma evansi.

  “Plant” in this specification refers to cereals and fruit trees / vegetables cultivated as human food, feed crops such as livestock and poultry, appreciation plants that love their form and shape, or planting in parks, streets, etc. It means a vascular plant (Tracheophyta), and specific examples include the following plants, but specific examples of plants are not limited to these.

  Pinaceae plants belonging to Pinaceae, such as Japanese red pine (Pinus densiflora), European red pine Scots Pine (Pinus sylvestris), Japanese black pine (Pinus thunbergii).

Pepper (Piper nigrum) such as Pepperaceae (Piperaceae), Avocado Avocado (Persea americana) and other magnoliaceae (Lauraceae) etc., magnoliids,
Konjac (Amorphophallus konjac), taro edode (Colocasia esculenta) and other taro (Araceae), Chinese yam (Dioscorea batatas), yam Japanese yam (Dioscorea japonica) and other yam (Dioscoreacesum var) porrum), Onion Onion (Allium cepa), Rakkyo Rakkyo (Allium chinense), Leek Welsh onion (Allium fistulosum), Garlic Garlic (Allium sativum), Chives Chives (Allium schoenoprasum), Asatsuchi Chive (Allium schoenofosum var) Japanese leek Oriental garlic (Allium tuberosum), Alliumaceae such as Scallion (Allium x wakegi), Asparagus Asparagus (Asparagus officinalis), etc. (Elaeis guineensis) and other palms (Arecaceae) arecaidea (Arecoideae), na Date palm (Phoenix dactylifera) and other palms (Arecaceae) Talipot subfamily (Coryphoideae), pineapples Pineapple (Ananas comosus) and other pineapples (Bromeliaceae), rice Rice (Poryae sativa) and other poaceae Family (Ehrhartoideae), bentgrass Bent grass (Agrostis spp.), Blue grass (Poa spp.), Barley Barley (Hordeum vulgare), wheat Wheat (Triticum aestivum, T. durum), rye Rye (Secale cereale), etc. Poaceae Strawberry subfamily (Pooideae), Googyushiba Bermuda grass (Cynodon dactylon), Shiba Grass (Zoysia spp.), Etc. Sorgum (Sorghum bicolor), Corn Corn (Zea mays), etc. Gramineae (Poaceae) Millet subfamily (Panicoideae), Banana Banana (Musa spp.), Etc. Monocots belonging to Zingiberaceae, such as Musaceae, Myoga (Zingiber mioga), Ginger (Zingiber officinale) and the like.

  Lotus root (Nelumbo nucifera) and other lotus families (Nelumbonaceae), groundnuts Peanut (Arachis hypogaea), chickpeas (Cicer arietinum), lentil Lentil (Lens culinaris), peas Pea (Pisum sativum), broad bean Bia bea , Soybean Soybean (Glycine max), common bean (Phaseolus vulgaris), adzuki bean (Vigna angularis) adzuki bean (Vigna angularis), legume (Fabaceae) such as cowpea (Vigna unguiculata), Asapaceae (Cannabaceae) such as hop Hop (Humulus lupulus) ), Fig Tree (Ficus carica), Mulberry (Morus spp.), Etc. (Moraceae), Jujube (Ziziphus jujuba), etc. (Rhamnaceae), Strawberry Strawberry (Fragaria), Rose Rose (Rosa) spp.) and other Rosaceae (Rosaceae) subfamily (Rosoideae), loquat Japanese loquat (Eriobotrya japonica), apple Apple (Malus pumila), pear European Pear ( Pyrus communis), pear Nashi Pear (Pyrus pyrifolia var. Culta) and other roses (Rosaceae) pear subfamily (Maloideae), peach Peach (Amygdalus persica), apricot Apricot (Prunus armeniaca), sweet cherry (Prunus avium), prunes Roses such as Prune (Prunus domestica), Almond Almond (Prunus dulcis), Japanese plum Apricot (Prunus mume), Japanese plum Plum (Prunus salicina), Oshima cherry (Cerasus speciosa), Yoshino cherry (Cerasus x yedoensis'Somei-yoshino ') (Rosaceae) Cherry subfamily (Prunoideae), Tougan Winter melon (Benincasa hispida), Watermelon Watermelon (Citrullus lanatus), Yugao Bottle gourd (Lagenaria siceraria var. Hispida), Loofah Luffa (Luffa cylindrica), Pumpkin Pumpkin (Pumpkin) , Zucchini (Cucurbita pepo), Bitter melon (Momordica charantia var. Pavel), Melon Muskmelon (Cucumis melo), Oriental pi culingis melon (Cucumis melo var. conomon), cucumber Oriental melon (Cucumis melo var. makuwa), cucumber Cucumber (Cucumis sativus) and other Cucurbitaceae, chestnut Japanese Chestnut (Castanea crenata) and other beech (Fagaceae) Walnut Walnut (Juglans spp.) And other walnuts (Juglandaceae), cashew nut Cashew (Anacardium occidentale), mango Mango (Mangifera indica), pistachio Pistachio (Pistacia vera), etc. ) Etc. (Rutaceae) Henruda subfamily (Rutoideae), Daidai Bitter orange (Citrus aurantium), Lime Lime (Citrus aurantifolia), Hassaku Hassaku orange (Citrus hassaku), Yuzu Yuzu (Citrus junos), Lemon Lemon (Citrus limon) ), Natsumikan (Citrus natsudaidai), Grapefruit (Citrus x paradisi), Orange Orange (Citrus sinensis) ), Kabosu Kabosu (Citrus sphaerocarpa), Sudachi (Citrus sudachi), Ponkan Mandarin Orange (Citrus tangerina), Satsuma (Citrus unshiu), Kumquat Kumquat (Fortunella spp.), Etc. Aurantioideae), Horseradish (Armoracia rusticana), Mustard (Brassica juncea), Takana Takana (Brassica juncea var. Integrifolia), Brassica rapeseed (Brassica napus), Cauliflower Cauliflower (Brassica oleCatratis var. oleracea var. capitata), brussels sprout (Brassica oleracea var. gemmifera), broccoli (Brassica oleracea var. italica), green pak choi (Brassica rapa var. chinensis), Nozawana (varassakapaura) Napa cabbage (Brassica rapa var. Nippo-oleifera), Mizuna Potherb Mustard (B rasposica rapa var. nipposinica), Chinese cabbage Napa cabbage (Brassica rapa var. pekinensis), Komatsuna Turnip leaf (Brassica rapa var. perviridis), Turnip Turnip (Brassica rapa var. rapa), Arugula Garden rocket (Eruca vesicaria) Raphanus sativus var. Longipinnatus), Wasabi (Wasabia japonica) and other Brassicaceae (Brassicaceae); , Cacao (Theobroma cacao) such as Malvaceae, Grapes Grape (Vitis spp.) Grapes (Vitaceae), sugar beet Sugar beet (Beta vulgaris ssp. Vulgaris var. Altissima), table beet Table beet (Beta vulgaris ssp. vulgaris var. vulgaris), Amaranthaceae such as spinach (Spinacia oleracea), Polygonaceae such as buckweat (Fagopyrum esculentum) , Kaki Persimmon (Diospyros kaki) and other oysters (Ebenaceae), Cha Tea plant (Camellia sinensis) and other camellia (Theaceae), Kiwifruit Kiwifruit (Actinidia deliciosa, A. chinensis) and other matabiaceae (Actinidiaceae), Blueberry (Vaccinium spp.), Cranberry Cranberry (Vaccinium spp.) And other azaleas (Ericaceae), Coffee tree Coffee plants (Coffea spp.) And other Rubiaceae, lemon balm Lemon balm (Melissa officinalis), mint Mint ( Mentha spp.), Basil Basil (Ocimum basilicum), Shiso Shiso (Perilla frutescens var. Crispa), Sesame (Perilla frutescens var. Frutescens), Sage Common Sage (Salvia officinalis), Thyme (Thymus spp.) (Lamiaceae), Sesame (Pedaliaceae) such as Sesame (Sesamum indicum), Oleaceae such as Olive Olive (Olea europaea), Sweet potato (I pomoea batatas), Convolvulaceae, Tomato (Solanum lycopersicum), Eggplant Eggplant (Solanum melongena), Potato Potato (Solanum tuberosum), Pepper Chili pepper (Capsicum annuum), Bell pepper (Capsicum annusum var. '), Solanaceae (Solanaceae) such as tobacco Tobacco (Nicotiana tabacum), celery Celery (Apium graveolens var. Dulce), coriander Coriander (Coriandrum sativum), Japanese honeywort (Cryptotaenia Canadensis subsp. Japonica), carrot carrot (Daucus carrot (Daucus subsp. sativus), parsley Parsley (Petroselium crispum), Italian parsley Italian parsley (Petroselinum neapolitanum), etc. (Apiaceae), Udo Udo (Aralia cordata), araki (Aralia elata), etc. Araliaceich, artichoke (Cynara scolymus) and other asteraceae (Asteraceae) thistle subfamily (Carduoideae), chrysanthemum Chicory (Cichorium intybus), Lettuce Lettuce (Lactuca sativa), etc. Authentic dicots (eudicots) belonging to Asteraceae and Asteraceae such as Fuki (Petasites japonicus) and Burdock (Arctium lappa).

  The term “animal” in the present specification means humans, companion animals, pets, livestock, poultry, and vertebrates such as research and laboratory animals. Specific examples include the following animals: However, specific examples of animals are not limited to these.

  Capuchin (Cebidae) such as Tufted capuchin (Cebus apella), Crab-eating macaque (Macaca fascicularis), Rhesus macaque (Macaca mulatta), etc. (Homo sapiens) such as Hominidae, European rabbit (Oryctolagus cuniculus) such as Rabidae (Leporidae), Chinchilla Long-tailed chinchilla (Chinchilla lanigera), Chinchillaidae, Guinea pig Guinea pig (Cavia porcellus) ) Guinea pigs (Caviidae), Golden hamster (Mesocricetus auratus), Dungarian hamster (Phodopus sungorus), Mongolian rat The house mouse ouse (Mus musculus), black rats (Rattus rattus) and other murines (Muridae), chipmunk (Samiuridae) such as Chipmunk (Tamias sibiricus), Dromedary (Camelus dromedarius), Bactrian actl (Camelus) Alpaca (Vicugna pacos), Camelidae such as Llama (Lama glama), Wild boar (Suidae) such as pig Pig (Sus scrofa domesticus), Reindeer Reindeer (Rangifer tarandus), Red deer (Cervus elaphus) Deer (Cervidae), Yak (Bos grunniens), Cattle Cattle (Bos taurus), Asian Buffalo Water buffalo (Bubalus arnee), Goat (Capra hircus), Sheep (Ovis aries), etc. Bovidae ), Cats (Felidae) such as Cat Cat (Felis silvestris catus), Dogs (Canis lupus familiaris), Dogs such as Red Fox (Vulpes vulpes), Canidae, -European mink (Mustela lutreola), American mink (Mustela vison), Ferret (Mustela putorius furo) etc. Weasel (Mustelidae), Donkey (Equus asinus), Horse Horse (Equus caballus), etc. Equidae), mammals belonging to the kangaroo family (Macropodidae) such as red kangaroo (Macropus rufus).

  Ostriches such as Ostrich Ostrich (Struthio camelus), Rheidae such as American rhea (Rhea americana), Emu Emu (Dromaius novaehollandiae), Dromaiidae, Grouse Ptarmigan (Lagopus muta) Wild turkey (Meleagris gallopavo), Japanese quail (Coturnix japonica), chicken Chiken (Gallus gallus domesticus), common pheasant (Phasianus colchicus), golden pheasant (Chrysolophus pictus), peafowl Phasianidae, Helmeted guineafowl (Numida meleagris), etc. ), Greylag goose (Anser anser), Sakatsu Lagan Swan goose (Anser cygnoides), Whooper swan (Cygnus cygnus), Mute swan (Cygnus olor) and other ducks (Anatidae), kingfisher Rock dove (Columba livia), pheasant oriental elia ore Pigeons such as turtle dove (Streptopelia turtur), Columbidae, Kibatan Sulphur-crested cockatoo (Cacatua galerita), Great White-winged Parakeet Galah (Eolophus roseicapilla), Cockatiel (Nymphicus hollandicus), Parrot family (Cacatuidae) (Agapornis roseicollis), Blue-and-yellow macaw (Ara ararauna), Macaw Scarlet Macaw (Ara macao), Budgerigar Budgerigar (Melopsittacus undulatus), African gray parrot (Psittacus erithacus), etc. Kyukancho Common hill myna (Gracula religiosa) etc. Striidae (Sturnidae), red vaginal red avadavat (Amandava amandava), zebra finch (Taeniopygia guttata), juvenile pine Bengalese finch (Lonchura striata var. Domestica), scorpionidae ldidae Birds (Aves) belonging to the family Atri (Fringillidae) such as the canary domestic canary (Serinus canaria domestica) and the European goldfinch (Carduelis carduelis).

  Veiled chameleon (Chamaeleo calyptratus), etc. Chameleonidae (Chamaeleonidae), Green iguana (Iguana iguana), Green anole Carolinaina anole (Anolis carolinensis), etc. Iguanidae, Nile monitor Lizards such as Water Monitor (Varanus salvator) Constrictor (Boa constrictor), etc. Boidae (Boidae), Indian python (Python molurus), Japanese snake Reticulated python (Python reticulatus), etc. (Chelydridae), Kisiga Diamondback terrapin (Malaclemys terrapin), red turtles Pond slider (Trachemys scripta), etc. (Testudinidae), soft-shelled turtle (Pelodiscus sinensis), etc. (Trionychidae), American alligator (American alligator (Alligator mississippiensis)), black caiman (Calmani) Reptile (Reptilia) belonging to Crocodylidae (Crocodylidae) such as siamensis).

  Carp Carp (Cyprinus carpio), Goldfish Goldfish (Carassius auratus auratus), Zebrafish Zebrafish (Danio rerio), etc. piranha (Pygocentrus nattereri), Neon tetra (Paracheirodon innesi), etc., Caracinaceae (Characidae), White-headed Snow Maraena whitefish (Coregonus lavaretus maraena), Coho salmon (Oncorhynchus kisutsh), Rainbow trout Rainbow trout (Oncorhynchu trout (Oncorhynchu trout) Oncorhynchus tshawytscha), Atlantic salmon (Salmo salar), Brown trout Brown trout (Salmo trutta) and other salmonids (Salmonidae); Pseudanthias squamipinnis), Que Longtoo th grouper (Epinephelus bruneus), grouper (Conifert grouper (Epinephelus septemfasciatus), etc.) dumerili), yellowtail, Japanese amberjack (Seriola quinqueradiata), etc. Carnidae, red sea bream (Pagrus major), etc. Cichlidae such as), Sababridae such as Pacific bluefin tuna (Thunnus orientalis), and Bonefish (Actinopterygii) belonging to Tetraodontidae such as Japanese pufferfish (Takifugu rubripes).

  The term “useful insects” in the present specification means insects that are useful for human life by using their products, or for improving the efficiency of agricultural work such as use for pollination of fruit trees and vegetables. For example, Japanese honeybee (Apis cerana japonica), Western honey bee (Apis mellifera), Bumblebee (Bombus consobrinus wittenburgi, B. diversus diversus, B. hypocrita hypocrita, B. ignitus, B. ignitus, B. terituris, B. terituris, B. terrestris, B. (Osmia cornifrons), silkworm Silkworm (Bombyx mori) and the like are mentioned, but specific examples of useful insects are not limited thereto.

  The term “natural enemy” in the present specification means an organism that kills or suppresses the growth of a specific species of organism, particularly a specific species that harms agricultural crops, by predation or parasitism. The following organisms are listed, but specific examples of natural enemies are not limited to these.

  Saccharomian leaflet (Dacnusa sasakawai), leaflet (Dacnusa sibirica), Colleman's wasp (Aphidius colemani), Apanteles glomeratus, Braconidae, pod, (Aphelinus asychis), cotton bee (Aphelinus gossypii), cross-horned bee (Aphelinus maculatus), wasp (Aphelinus varipes), bee (Encarsia formosa), beetle (Eretmocerus eremicus) mundus and other species such as Aphelinidae and Chrysocharis pentheus, Neochrysocharis formosa, Diglyphus isaea, and Hemiptarsenus Parasitic wasp belonging to the family (Eulophidae), etc .; Aphidophagous gall midge (Aphidoletes aphidimyza); Nan-spot ladybird (Coccinella septempunctata); japonica); Orius minutus, Orius nagaii, Orius sauteri, and the giant pirate bug (Orius strigicollis) Predatory stink bug Anthocorid predatory bug; predatory stink bug Predatory mirid belonging to Miridae such as Pilophorus typicus and Nesidiocoris tenuis; Frankpirip Aeolothrip Predatory thrips belonging to idae; Green lacewing belonging to the family Chrysopidae such as Dichochrysa formosanus and Chrysoperla nipponensis; ), Amblyseius degenerans, Amblyseius swirskii, Phytoseiulus persimilis, etc. (Misumenops tricuspidatus).

  The compound of the present invention represented by the formula (I) can be produced, for example, by the following method.

  Manufacturing method A

Formula (II) [wherein Y ¹ , Y ² , Y ³ , Y ⁴ , R ¹ , R ² , R ³ , R ⁴ and R ⁵ represent the same meaning as described above. Or a salt thereof (for example, hydrochloride, hydrobromide, trifluoroacetate, p-toluenesulfonate, etc.) and a compound represented by formula (III) [wherein G ¹ is J ¹ represents the same meaning as described above, and J ¹ represents a chlorine atom, a bromine atom, a C ₁ -C ₄ alkylcarbonyloxy group (for example, pivaloyloxy group), a C ₁ -C ₄ alkoxycarbonyloxy group (for example, isobutyloxycarbonyloxy group). Or an azolyl group (for example, imidazol-1-yl group) etc. are represented. ], If necessary, benzene, toluene, dichloromethane, chloroform, 1,2-dichloroethane, diethyl ether, tert-butyl methyl ether, tetrahydrofuran, 1,4-dioxane, ethyl acetate, N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, water or a mixture of two or more of them in an arbitrary ratio is used as a solvent, and if necessary, 1 to 3 equivalents of sodium carbonate with respect to 1 equivalent of the compound represented by formula (II) , Potassium carbonate, sodium bicarbonate, sodium acetate, triethylamine, ethyldiisopropylamine, N-methylmorpholine, pyridine, 4- (dimethylamino) pyridine and the like in the presence of a base such as 0 ° C. to the reflux temperature of the reaction mixture. By reacting for 24 minutes, the formula (Ia) wherein W is an oxygen atom in formula (I) [Wherein G ¹ , Y ¹ , Y ² , Y ³ , Y ⁴ , R ¹ , R ² , R ³ , R ⁴ and R ⁵ represent the same meaning as described above]. This invention compound represented by this can be obtained.

  Some of the compounds represented by the formula (III) used here are known compounds, and some of them are commercially available. In addition, other known methods corresponding to the known methods described in the literature, for example, the methods described in Journal of Medicinal Chemistry [J. Med. Chem.] 1991, 34, 1630, etc. A method of reacting a carboxylic acid with a halogenating agent such as thionyl chloride, phosphorus pentachloride or oxalyl chloride, Tetrahedron Lett. 2003, 44, 4819, Journal of Medicinal Chemistry [J. Med. Chem.] 1991, 34, 222, etc., corresponding known carboxylic acid in the presence of an organic acid halide such as pivaloyl chloride or isobutyl chloroformate, and if necessary in the presence of a base, Method of reaction, or The Journal of Organic Chemistry [J. Org. Chem.] 1989, 54, 5620 It can be readily synthesized using methods such as reacting the corresponding carbonyl known carboxylic acid diimidazole or sulfonyl diimidazole, etc. according to equal.

  Manufacturing method B

Formula (Ib) wherein W is an oxygen atom and R ⁵ is a hydrogen atom in formula (I) [wherein G ¹ , Y ¹ , Y ² , Y ³ , Y ⁴ , R ¹ , R ² , R ³ And R ⁴ represent the same meaning as described above. And 1 to 10 equivalents of formula (IV) [wherein R ⁵ represents the same meaning as described above except for a hydrogen atom and C ₁ -C ₄ alkoxy, and J ² represents a chlorine atom. , bromine atom, iodine atom, C ₁ -C ₄ alkylcarbonyloxy group (e.g., pivaloyloxy group, etc.), C ₁ -C ₄ alkyl sulfonate group (e.g., methanesulfonyloxy group, etc.), C ₁ -C ₄ haloalkyl sulfonate group Good elimination of (for example, trifluoromethanesulfonyloxy group), aryl sulfonate group (for example, benzenesulfonyloxy group, p-toluenesulfonyloxy group, etc.) or azolyl group (for example, imidazol-1-yl group, etc.) Represents a group. Or a polar solvent such as tert-butyl methyl ether, tetrahydrofuran, 1,4-dioxane, acetonitrile or N, N-dimethylformamide if necessary, and represented by the formula (Ib) if necessary. In the presence of a base such as 1 to 3 equivalents of sodium hydride, potassium tert-butoxide, potassium hydroxide, potassium carbonate, triethylamine, pyridine, etc. By reacting for a time, the formula (Ia) in which W is an oxygen atom in the formula (I) [wherein G ¹ , Y ¹ , Y ² , Y ³ , Y ⁴ , R ¹ , R ² , R ³ , R ⁴ and R ⁵ represent the same meaning as described above. This invention compound represented by this can be obtained.

  Some of the compounds represented by the formula (IV) used here are known compounds, and some of them are commercially available. In addition, other synthetic methods described in the literature relating to known compounds, for example, Chemical and Pharmaceutical Bulletin [Chem. Pharm. Bull.] 1986, 34, 540 and 2001, 49 Volume 1102, Journal of the American Chemical Society [J. Am. Chem. Soc.] 1964, 86, 4383, The Journal of Organic Chemistry [J. Org. Chem 1983, 48, 5280, Organic Synthesis [Org. Synth.] 1988, Collective Volume 6, 101, Synlett 2005, 2847, Synthesis 1990, 1159 , Japanese Patent Application Publication (JP 05/125017 Publication), European Patent Publication (EP 0,051,273 Publication) ) And the method described in British Patent Gazette (GB 2,161,802) and the like.

  Manufacturing method C

Formula (Ia) wherein W is an oxygen atom in Formula (I) [wherein G ¹ , Y ¹ , Y ² , Y ³ , Y ⁴ , R ¹ , R ² , R ³ , R ⁴ and R ⁵ are Means the same. And 1-10 equivalents of diphosphorus pentasulfide, diphosphorus pentasulfide-HMDO (hexamethyldisiloxane) or Lawesson's Reagent; 2,4-bis (4-methoxyphenyl) ) -1,3,4,4-dithiadiphosphetane = 2,4-disulfide), etc., and if necessary, benzene, toluene, chlorobenzene, dichloromethane, chloroform, 1,2-dimethoxyethane, tetrahydrofuran 1,4-dioxane or HMPA is used as a solvent, and if necessary, in the presence of 1 to 4 equivalents of a base such as sodium bicarbonate, triethylamine or pyridine with respect to 1 equivalent of the compound represented by the formula (Ia) at room temperature The reaction mixture is allowed to react for 10 minutes to 50 hours in the temperature range of the reflux temperature of the reaction mixture, or 80 ° C. to the reflux temperature of the reaction mixture using pyridine as a base in a solvent amount. In degrees range, by reacting 1 to 3 hours, W has the formula (Ic) [wherein a sulfur atom in the formula ^{(I), G 1, Y} 1, Y 2, Y 3, Y 4, R 1, R ² , R ³ , R ⁴ and R ⁵ represent the same meaning as described above. This invention compound represented by this can be obtained.

  In production method A to production method C, the reaction mixture after completion of the reaction is directly concentrated or dissolved in an organic solvent, concentrated after washing with water, or poured into ice water, and subjected to usual post-treatment such as concentration after extraction with organic solvent. N-alkenyl-substituted amide compounds can be obtained. Moreover, when the necessity for purification arises, it can be separated and purified by any purification method such as recrystallization, column chromatograph, thin layer chromatograph, liquid chromatographic fractionation and the like.

  The compound represented by the formula (II) used in the production method A can be synthesized, for example, as shown in the reaction formulas 1 to 4.

  Reaction formula 1

Formula (V) [wherein Y ¹ , Y ² , Y ³ , Y ⁴ , R ³ and R ⁴ represent the same meaning as described above. And a compound represented by formula (VI) [wherein R ¹ and R ² represent the same meaning as described above, provided that at least one of R ¹ or R ² is a hydrogen atom, J ³ is a chlorine atom, A bromine atom or an iodine atom is represented. ], For example, Angewante Chemie International Edition [Angew. Chemie, Int. Ed.] 2011, 50, 2593, Organic Letters [Organic. Lett.] 2007, 9 5219, The Journal of Organic Chemistry [J. Org. Chem.] 1993, 58, 6509, Tetrahedron 2010, 66, 3499, European Journal of In accordance with the method described in Organic Chemistry [European J. Org. Chem.] 2007, 266, etc., presence of strong base such as potassium tert-butoxide, sodium hexamethyldisilazide, lithium diisopropylamide, alkyllithium, etc. By reacting under the formula (VII) [wherein Y ¹ , Y ² , Y ³ , Y ⁴ , R ¹ , R ² , R ³ and R ⁴ represent the same meaning as described above. ] Can be synthesized.

Next, the compound represented by the formula (VII) is dissolved in toluene, dichloromethane, chloroform, methanol, ethanol, tetrahydrofuran, 1,4-dioxane, water or a mixture of two or more of them in any ratio if necessary. 1 to 4 equivalents of methylamine aqueous solution, hydrazine aqueous solution or hydrazine monohydrate with respect to 1 equivalent of the compound represented by formula (VII) under an inert gas atmosphere such as nitrogen or argon if necessary and room temperature -By reacting in the temperature range of the reflux temperature of the reaction mixture for 1 to 24 hours, the formula (IIa) in which R ⁵ is a hydrogen atom in the formula (II) [wherein Y ¹ , Y ² , Y ³ , Y ⁴ , R ¹ , R ² , R ³ and R ⁴ have the same meaning as above. The compound represented by this can be obtained.

  Some of the compounds represented by the formula (VI) used here are known compounds, and some of them are available as commercial products. In addition, other compounds can be easily synthesized according to general synthesis methods described in literatures concerning known compounds.

  Reaction formula 2

Formula (VIII) [wherein Y ¹ , Y ² , Y ³ , Y ⁴ , R ³ and R ⁴ represent the same meaning as above, and R ⁵ represents —C (O) R ¹¹ and C ₁ -C ₄ alkoxy. The same meaning as described above other than carbonyl is represented. And a compound represented by formula (VI) [wherein R ¹ and R ² represent the same meaning as described above, provided that at least one of R ¹ or R ² is a hydrogen atom, J ³ is a chlorine atom, A bromine atom or an iodine atom is represented. The compound represented by formula (VIII) is reacted with, for example, Journal of Medicinal Chemistry [J. Med. Chem.] 2009. According to the method described in Vol. 52, p. 3679, Organic Letters [Organic. Lett.] 2011, p. 13, 2614, etc. Thus, formula (IX) [wherein Y ¹ , Y ² , Y ³ , Y ⁴ , R ¹ , R ² , R ³ , R ⁴ and R ⁵ represent the same meaning as described above. ] Can be synthesized.

Next, the compound represented by the formula (IX) is deprotected, for example, by reacting with hydrochloric acid, hydrobromic acid, trifluoroacetic acid, p-toluenesulfonic acid, etc. Among them, Y ¹ , Y ² , Y ³ , Y ⁴ , R ¹ , R ² , R ³ , R ⁴ and R ⁵ represent the same meaning as above. Or a salt thereof (for example, hydrochloride, hydrobromide, trifluoroacetate, p-toluenesulfonate, etc.).

  Reaction formula 3

For example, Tetrahedron Lett. 2010, 51, 357, Bioorganic & Med. Chem. 2007, 15, 5262, Organic Letters [Organic. Lett.] According to the method described in 2009, Vol. 11, p. 345, etc., the formula (X) [wherein Y ¹ , Y ² , Y ³ and Y ⁴ represent the same meaning as described above, and J ⁴ represents A chlorine atom, a bromine atom, an iodine atom or a trifluoromethanesulfonyloxy group is represented. [Wherein Y ¹ , Y ² , Y ³ and Y ⁴ represent the same meaning as described above, and M represents a —ZnCl group, a —ZnBr group, a —ZnI group. , -B (OH) ₂ group or 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl group and the like. And a compound represented by formula (XII) [wherein R ¹ , R ² , R ³ and R ⁴ represent the same meaning as described above, J ⁵ represents a bromine atom, an iodine atom or a trifluoromethanesulfonyloxy group, etc. Represent. And a compound represented by formula (VII) [wherein Y ¹ , Y ² , Y ³ , Y ⁴ , R ¹ , R ² , R ³ and R ⁴ represent the same meaning as described above. ] Can be synthesized.

Next, by reacting the compound represented by the formula (VII) under the same conditions as in the reaction formula 1, the formula (IIa) in which R ⁵ is a hydrogen atom in the formula (II) [wherein Y ¹ , Y ² , Y ³ , Y ⁴ , R ¹ , R ² , R ³ and R ⁴ represent the same meaning as described above. The compound represented by this can be obtained.

  Some of the compounds represented by the formula (X) used here are known compounds, and some of them are available as commercial products. In addition, other compounds can be easily synthesized according to general synthesis methods described in literatures concerning known compounds.

  Reaction formula 4

Under the same conditions as in Reaction Scheme 3, formula (XI) [wherein Y ¹ , Y ² , Y ³ , Y ⁴ and M represent the same meaning as described above. And a compound represented by formula (XIII) [wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ and J ⁵ represent the same meaning as described above. And a compound represented by formula (IX) [wherein Y ¹ , Y ² , Y ³ , Y ⁴ , R ¹ , R ² , R ³ , R ⁴ and R ⁵ are as described above] Represents the same meaning. ] Can be synthesized.

Next, the compound represented by the formula (IX) is deprotected in the same manner as in the reaction formula 3, thereby obtaining the formula (II) [wherein Y ¹ , Y ² , Y ³ , Y ⁴ , R ¹ , R ² , R ³ , R ⁴ and R ⁵ represent the same meaning as above. Or a salt thereof (for example, hydrochloride, hydrobromide, trifluoroacetate, p-toluenesulfonate, etc.).

  The compound represented by Formula (V) used in Reaction Scheme 1 can be synthesized, for example, as follows.

  Reaction formula 5

That is, formula (XIV) [wherein Y ¹ , Y ² , Y ³ , Y ⁴ , R ³ , R ⁴ and J ³ represent the same meaning as described above. And 1 to 1.5 equivalents of potassium phthalimide, for example, toluene, dichloromethane, tetrahydrofuran, 1,4-dioxane, acetone, N, N-dimethylformamide, N, N-dimethylacetamide, Dimethyl sulfoxide or the like is used as a solvent, and if necessary, in the presence of 0.1 to 2 equivalents of a base such as sodium carbonate, potassium carbonate or sodium bicarbonate, and 0.1 to 1 equivalents of tetrabutylammonium iodide as a catalyst if necessary. , Tributylhexadecylphosphonium bromide, crown ether (18-Crown-6) and the like, and the reaction is carried out in the temperature range of room temperature to the reflux temperature of the reaction mixture for 0.5 to 24 hours. , Y ¹ , Y ² , Y ³ , Y ⁴ , R ³ and R ⁴ represent the same meaning as described above. ] Can be synthesized.

  Some of the compounds represented by the formula (XIV) used here are known compounds, and some of them are available as commercial products. In addition, other compounds can be easily synthesized according to general synthesis methods described in literatures concerning known compounds.

  The compound represented by Formula (VIII) used in Reaction Scheme 2 can be synthesized, for example, as follows.

  Reaction formula 6

That is, formula (XV) [wherein R ³ , R ⁴ and R ⁵ represent the same meaning as described above. ], For example, Journal of Medicinal Chemistry [J. Med. Chem.] 2004, 47, 6884, Bioorganic & Medicinal Chemistry Letters [Bioorganic & Med. Chem. Lett.] Formula (XVI) which can be synthesized by reacting using the method described in 2012, Vol. 22, p. 5485, etc. [wherein R ³ , R ⁴ and R ⁵ represent the same meaning as described above, J ⁶ represents a dimethylamino group, an N-methylmethoxyamino group, a piperidin-1-yl group, a benzotriazol-1-yl group, or the like. ], For example, Tetrahedron Lett. 2002, 43, 8223 and 2005, 46, 8587, The Journal of Organic Chemistry [J. Org. Chem. 2006, 71, 9861, etc., according to a known formula (XVII) [wherein Y ¹ , Y ² , Y ³ and Y ⁴ represent the same meaning as described above, ⁷ represents a hydrogen atom, a chlorine atom, a bromine atom or an iodine atom. A compound represented by formula (XI), wherein Y ¹ , Y ² , Y ³ and Y ⁴ represent the same meaning as described above, Represents Li, MgCl, MgBr, MgI or the like. By reacting with a compound represented by formula (VIII), Y ¹ , Y ² , Y ³ , Y ⁴ , R ³ , R ⁴ and R ⁵ have the same meaning as described above. The compound represented by this can be obtained.

  Some of the compounds represented by the formula (XV) used here are known compounds, and some of them are available as commercial products. In addition, other compounds can be easily synthesized according to general synthesis methods described in literatures concerning known compounds.

  The compound represented by the formula (XII) used in the reaction formula 3 can be synthesized, for example, as follows.

  Reaction formula 7

That is, a compound represented by the formula (XVIII) [wherein R ¹ , R ² , R ³ , R ⁴ , J ³ and J ⁵ represent the same meaning as described above. ] And potassium phthalimide are reacted under the same conditions as in Reaction Scheme 5 to form Formula (XII) [wherein R ¹ , R ² , R ³ , R ⁴ and J ⁵ represent the same meaning as described above. . The compound represented by this can be obtained.

  Some of the compounds represented by the formula (XVIII) used here are known compounds, and some of them are available as commercial products. In addition, other compounds can be easily synthesized according to general synthesis methods described in literatures concerning known compounds.

  The compound represented by Formula (XIII) used in Reaction Scheme 4 can be synthesized, for example, as follows.

  Reaction formula 8

That is, formula (XIX) [wherein R ¹ , R ² , R ³ , R ⁴ and J ⁵ represent the same meaning as described above, and R ⁵ represents —C (O) R ¹¹ and C _{1 to} C ₄ alkoxycarbonyl. Other than the above, the same meaning as described above is expressed. ] And di-tert-butyl dicarbonate, for example, European Journal of Organic Chemistry [European J. Org. Chem.] 2001, 1673, Heterocycles 2008 75, page 107, etc., by reacting in accordance with the formula (XIII) [wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ and J ⁵ have the same meaning as above. Represent. ] Can be synthesized.

  Some of the compounds represented by the formula (XIX) used here are known compounds, and some of them are available as commercial products. In addition, other compounds can be easily synthesized according to general synthesis methods described in literatures concerning known compounds.

  In each of these reactions, after the completion of the reaction, each of the production intermediates that are the raw material compounds of production method A to production method C can be obtained by performing a general post-treatment.

  In addition, each production intermediate produced by these methods can be used as it is in the subsequent step without isolation and purification.

  Specific examples of the N-alkenyl-substituted amide compound represented by the formula (I) included in the present invention that can be produced using these methods include the compounds shown in Table 2. However, the compounds in Table 2 are for illustrative purposes, and the N-alkenyl-substituted amide compounds encompassed by the present invention are not limited to these.

In the table, Et represents an ethyl group, and similarly, n-Pr represents a normal propyl group, i-Pr represents an isopropyl group, c-Pr and Pr-c represent a cyclopropyl group, n-Pr Bu is a normal butyl group, i-Bu and Bu-i are isobutyl groups, s-Bu and Bu-s are secondary butyl groups, c-Bu and Bu-c are cyclobutyl groups, t-Bu and Bu-- t represents a tertiary butyl group, Pen represents a pentyl group, Pen-c represents a cyclopentyl group, Hex represents a hexyl group, c-Hex represents a cyclohexyl group,
In the table, D-7 represents an aromatic heterocyclic ring represented by the following structural formula.

Table 2

――――――――――――――――――――――――――――――――――――――――
R ⁵ R ³ R ⁴ R ¹ R ² Y ¹ Y ² Y ³ Y ⁴
――――――――――――――――――――――――――――――――――――――――
HHHHHFH Cl H
H CH ₃ HHHFH Cl H
HHHHHFH Br H
H CH ₃ HHHFH Br H
HHHHHFH CF ₃ H
H CH ₃ HHHFH CF ₃ H
HHHHH Cl HFH
H CH ₃ HHH Cl HFH
HHHHH Cl H Cl H
CH ₃ HHHH Cl H Cl H
Et HHHH Cl H Cl H
i-Pr HHHH Cl H Cl H
c-Pr HHHH Cl H Cl H
c-Bu HHHH Cl H Cl H
CH ₂ CHF ₂ HHHH Cl H Cl H
CH ₂ OCH ₃ HHHH Cl H Cl H
CH ₂ OEt HHHH Cl H Cl H
CH ₂ OC (O) CH ₃ HHHH Cl H Cl H
CH ₂ OC (O) OCH ₃ HHHH Cl H Cl H
CH ₂ SCH ₃ HHHH Cl H Cl H
CH ₂ CN HHHH Cl H Cl H
CH ₂ C (O) OCH ₃ HHHH Cl H Cl H
CH ₂ C (O) NH ₂ HHHH Cl H Cl H
CH ₂ C (S) NH ₂ HHHH Cl H Cl H
CH ₂ CH = CH ₂ HHHH Cl H Cl H
CH ₂ C≡CH HHHH Cl H Cl H
OCH ₃ HHHH Cl H Cl H
OEt HHHH Cl H Cl H
SCCl ₃ HHHH Cl H Cl H
C (O) CH ₃ HHHH Cl H Cl H
C (O) OCH ₃ HHHH Cl H Cl H
H CH ₃ HHH Cl H Cl H
H Et HHH Cl H Cl H
H CH ₂ FHHH Cl H Cl H
H CF ₃ HHH Cl H Cl H
H CH ₂ OCH ₃ HHH Cl H Cl H
H CH ₂ SCH ₃ HHH Cl H Cl H
H CH ₃ CH ₃ HH Cl H Cl H
H -CH ₂ CH ₂ -HH Cl H Cl H
HHHFH Cl H Cl H
HHHHF Cl H Cl H
c-Pr HHFH Cl H Cl H
c-Pr HHHF Cl H Cl H
OCH ₃ HHFH Cl H Cl H
OCH ₃ HHHF Cl H Cl H
SCCl ₃ HHFH Cl H Cl H
SCCl ₃ HHHF Cl H Cl H
C (O) CH ₃ HHFH Cl H Cl H
C (O) CH ₃ HHHF Cl H Cl H
C (O) OCH ₃ HHFH Cl H Cl H
C (O) OCH ₃ HHHF Cl H Cl H
H CH ₃ HFH Cl H Cl H
H CH ₃ HHF Cl H Cl H
H CH ₂ FHFH Cl H Cl H
H CH ₂ FHHF Cl H Cl H
H -CH ₂ CH ₂ -FH Cl H Cl H
H -CH ₂ CH ₂ -HF Cl H Cl H
HHHFF Cl H Cl H
HHH Cl H Cl H Cl H
HHHH Cl Cl H Cl H
c-Pr HH Cl H Cl H Cl H
c-Pr HHH Cl Cl H Cl H
OCH ₃ HH Cl H Cl H Cl H
OCH ₃ HHH Cl Cl H Cl H
SCCl ₃ HH Cl H Cl H Cl H
SCCl ₃ HHH Cl Cl H Cl H
C (O) CH ₃ HH Cl H Cl H Cl H
C (O) CH ₃ HHH Cl Cl H Cl H
C (O) OCH ₃ HH Cl H Cl H Cl H
C (O) OCH ₃ HHH Cl Cl H Cl H
H CH ₃ H Cl H Cl H Cl H
H CH ₃ HH Cl Cl H Cl H
H CH ₂ FH Cl H Cl H Cl H
H CH ₂ FHH Cl Cl H Cl H
H -CH ₂ CH ₂ -Cl H Cl H Cl H
H -CH ₂ CH ₂ -H Cl Cl H Cl H
HHH Cl Cl Cl H Cl H
HHH CH ₃ H Cl H Cl H
HHHH CH ₃ Cl H Cl H
c-Pr HH CH ₃ H Cl H Cl H
c-Pr HHH CH ₃ Cl H Cl H
OCH ₃ HH CH ₃ H Cl H Cl H
OCH ₃ HHH CH ₃ Cl H Cl H
SCCl ₃ HH CH ₃ H Cl H Cl H
SCCl ₃ HHH CH ₃ Cl H Cl H
C (O) CH ₃ HH CH ₃ H Cl H Cl H
C (O) CH ₃ HHH CH ₃ Cl H Cl H
C (O) OCH ₃ HH CH ₃ H Cl H Cl H
C (O) OCH ₃ HHH CH ₃ Cl H Cl H
H CH ₃ H CH ₃ H Cl H Cl H
H CH ₃ HH CH ₃ Cl H Cl H
H CH ₂ FH CH ₃ H Cl H Cl H
H CH ₂ FHH CH ₃ Cl H Cl H
_{H -CH 2 CH 2 - CH 3} H Cl H Cl H
H -CH ₂ CH ₂ -H CH ₃ Cl H Cl H
HHH Et H Cl H Cl H
HHHH Et Cl H Cl H
H CH ₃ H Et H Cl H Cl H
H CH ₃ HH Et Cl H Cl H
HHH n-Pr H Cl H Cl H
HHHH n-Pr Cl H Cl H
H CH ₃ H n-Pr H Cl H Cl H
H CH ₃ HH n-Pr Cl H Cl H
HHH i-Pr H Cl H Cl H
HHHH i-Pr Cl H Cl H
H CH ₃ H i-Pr H Cl H Cl H
H CH ₃ HH i-Pr Cl H Cl H
HHH c-Pr H Cl H Cl H
HHHH c-Pr Cl H Cl H
H CH ₃ H c-Pr H Cl H Cl H
H CH ₃ HH c-Pr Cl H Cl H
HHH n-Bu H Cl H Cl H
HHHH n-Bu Cl H Cl H
HHH i-Bu H Cl H Cl H
HHHH i-Bu Cl H Cl H
HHH CH ₂ Pr-c H Cl H Cl H
HHHH CH ₂ Pr-c Cl H Cl H
HHH s-Bu H Cl H Cl H
HHHH s-Bu Cl H Cl H
HHH t-Bu H Cl H Cl H
HHHH t-Bu Cl H Cl H
HHH Pen H Cl H Cl H
HHHH Pen Cl H Cl H
HHH CH ₂ Bu-i H Cl H Cl H
HHHH CH ₂ Bu-i Cl H Cl H
HHH CH ₂ Bu-s H Cl H Cl H
HHHH CH ₂ Bu-s Cl H Cl H
HHH CH ₂ Bu-c H Cl H Cl H
HHHH CH ₂ Bu-c Cl H Cl H
HHH CH ₂ Bu-t H Cl H Cl H
HHHH CH ₂ Bu-t Cl H Cl H
HHH Hex H Cl H Cl H
HHHH Hex Cl H Cl H
HHH CH ₂ CH (Et) ₂ H Cl H Cl H
HHHH CH ₂ CH (Et) ₂ Cl H Cl H
HHH CH ₂ Pen-c H Cl H Cl H
HHHH CH ₂ Pen-c Cl H Cl H
HHH c-Hex H Cl H Cl H
HHHH c-Hex Cl H Cl H
HHH CH ₂ OCH ₃ H Cl H Cl H
HHHH CH ₂ OCH ₃ Cl H Cl H
HHH OCH ₃ H Cl H Cl H
HHHH OCH ₃ Cl H Cl H
HHH NO ₂ H Cl H Cl H
HHHH NO ₂ Cl H Cl H
HHHHH Cl H Cl F
c-Pr HHHH Cl H Cl F
H CH ₃ HHH Cl H Cl F
H CH ₂ FHHH Cl H Cl F
H -CH ₂ CH ₂ -HH Cl H Cl F
HHHFH Cl H Cl F
HHHHF Cl H Cl F
HHH Cl H Cl H Cl F
HHHH Cl Cl H Cl F
HHH CH ₃ H Cl H Cl F
HHHH CH ₃ Cl H Cl F
HHHHH Cl H Cl Cl
c-Pr HHHH Cl H Cl Cl
H CH ₃ HHH Cl H Cl Cl
H CH ₂ FHHH Cl H Cl Cl
H -CH ₂ CH ₂ -HH Cl H Cl Cl
HHHFH Cl H Cl Cl
HHHHF Cl H Cl Cl
HHH Cl H Cl H Cl Cl
HHHH Cl Cl H Cl Cl
HHH CH ₃ H Cl H Cl Cl
HHHH CH ₃ Cl H Cl Cl
HHHHH Cl H Br H
c-Pr HHHH Cl H Br H
H CH ₃ HHH Cl H Br H
H CH ₂ FHHH Cl H Br H
H -CH ₂ CH ₂ -HH Cl H Br H
HHHFH Cl H Br H
HHHHF Cl H Br H
HHH Cl H Cl H Br H
HHHH Cl Cl H Br H
HHH CH ₃ H Cl H Br H
HHHH CH ₃ Cl H Br H
HHHHH Cl H CHF ₂ H
HHHHH Cl H CF ₃ H
c-Pr HHHH Cl H CF ₃ H
H CH ₃ HHH Cl H CF ₃ H
H CH ₂ FHHH Cl H CF ₃ H
H -CH ₂ CH ₂ -HH Cl H CF ₃ H
HHHFH Cl H CF ₃ H
HHHHF Cl H CF ₃ H
HHH Cl H Cl H CF ₃ H
HHHH Cl Cl H CF ₃ H
HHH CH ₃ H Cl H CF ₃ H
HHHH CH ₃ Cl H CF ₃ H
HHHHH Cl H OCHF ₂ H
HHHHH Cl H OCF ₃ H
HHHHH Cl H OCF ₂ Cl H
HHHHH Cl H OCF ₂ Br H
HHHHH Cl H OCH ₂ CF ₃ H
c-Pr HHHH Cl H OCH ₂ CF ₃ H
H CH ₃ HHH Cl H OCH ₂ CF ₃ H
H CH ₂ FHHH Cl H OCH ₂ CF ₃ H
_{H -CH 2 CH 2 - HH Cl} H OCH 2 CF 3 H
HHHFH Cl H OCH ₂ CF ₃ H
HHHHF Cl H OCH ₂ CF ₃ H
HHH Cl H Cl H OCH ₂ CF ₃ H
HHHH Cl Cl H OCH ₂ CF ₃ H
HHH CH ₃ H Cl H OCH ₂ CF ₃ H
HHHH CH ₃ Cl H OCH ₂ CF ₃ H
HHHHH Cl H CH = NOCH ₃ H
HHHHH Cl H CH = NOEt H
HHHHH Cl HC (CH ₃ ) = NOCH ₃ H
HHHHH Cl HC (CH ₃ ) = NOEt H
HHHHH Cl HC (Et) = NOCH ₃ H
HHHHH Cl H (D-7) -3-Cl H
HHHFH Cl H (D-7) -3-Cl H
HHHHF Cl H (D-7) -3-Cl H
HHH Cl H Cl H (D-7) -3-Cl H
HHHH Cl Cl H (D-7) -3-Cl H
HHH CH ₃ H Cl H (D-7) -3-Cl H
HHHH CH ₃ Cl H (D-7) -3-Cl H
HHHHH Cl H (D-7) -3-Br H
HHHFH Cl H (D-7) -3-Br H
HHHHF Cl H (D-7) -3-Br H
HHH Cl H Cl H (D-7) -3-Br H
HHHH Cl Cl H (D-7) -3-Br H
HHH CH ₃ H Cl H (D-7) -3-Br H
HHHH CH ₃ Cl H (D-7) -3-Br H
HHHHH Cl H (D-7) -3-CF ₃ H
HHHFH Cl H (D-7) -3-CF ₃ H
HHHHF Cl H (D-7) -3-CF ₃ H
HHH Cl H Cl H (D-7) -3-CF ₃ H
HHHH Cl Cl H (D-7) -3-CF ₃ H
HHH CH ₃ H Cl H (D-7) -3-CF ₃ H
HHHH CH ₃ Cl H (D-7) -3-CF ₃ H
HHHHH Cl F Cl H
c-Pr HHHH Cl F Cl H
H CH ₃ HHH Cl F Cl H
H CH ₂ FHHH Cl F Cl H
H -CH ₂ CH ₂ -HH Cl F Cl H
HHHFH Cl F Cl H
HHHHF Cl F Cl H
HHH Cl H Cl F Cl H
HHHH Cl Cl F Cl H
HHH CH ₃ H Cl F Cl H
HHHH CH ₃ Cl F Cl H
HHHHH Cl Cl Cl H
c-Pr HHHH Cl Cl Cl H
H CH ₃ HHH Cl Cl Cl H
H CH ₂ FHHH Cl Cl Cl H
H -CH ₂ CH ₂ -HH Cl Cl Cl H
HHHFH Cl Cl Cl H
HHHHF Cl Cl Cl H
HHH Cl H Cl Cl Cl H
HHHH Cl Cl Cl Cl H
HHH CH ₃ H Cl Cl Cl H
HHHH CH ₃ Cl Cl Cl H
HHHHH Cl Br Cl H
HHHHH Cl CH ₃ Cl H
HHHHH Cl CH ₂ OCH ₃ Cl H
HHHHH Cl CH ₂ SCH ₃ Cl H
HHHHH Cl CH ₂ SO ₂ CH ₃ Cl H
HHHHH Cl OCH ₃ Cl H
c-Pr HHHH Cl OCH ₃ Cl H
H CH ₃ HHH Cl OCH ₃ Cl H
H CH ₂ FHHH Cl OCH ₃ Cl H
_{H -CH 2 CH 2 - HH Cl} OCH 3 Cl H
HHHFH Cl OCH ₃ Cl H
HHHHF Cl OCH ₃ Cl H
HHH Cl H Cl OCH ₃ Cl H
HHHH Cl Cl OCH ₃ Cl H
HHH CH ₃ H Cl OCH ₃ Cl H
HHHH CH ₃ Cl OCH ₃ Cl H
HHHHH Cl OEt Cl H
c-Pr HHHH Cl OEt Cl H
H CH ₃ HHH Cl OEt Cl H
H CH ₂ FHHH Cl OEt Cl H
H -CH ₂ CH ₂ -HH Cl OEt Cl H
HHHFH Cl OEt Cl H
HHHHF Cl OEt Cl H
HHH Cl H Cl OEt Cl H
HHHH Cl Cl OEt Cl H
HHH CH ₃ H Cl OEt Cl H
HHHH CH ₃ Cl OEt Cl H
HHHHH Cl SCH ₃ Cl H
HHHHH Br H Cl H
HHHHH Br H Br H
c-Pr HHHH Br H Br H
H CH ₃ HHH Br H Br H
H CH ₂ FHHH Br H Br H
H -CH ₂ CH ₂ -HH Br H Br H
HHHFH Br H Br H
HHHHF Br H Br H
HHH Cl H Br H Br H
HHHH Cl Br H Br H
HHH CH ₃ H Br H Br H
HHHH CH ₃ Br H Br H
HHHHH Br H CF ₃ H
HHHHH Br CH ₃ Br H
HHHHH CH ₃ H Cl H
HHHHH CH ₃ H CF ₃ H
――――――――――――――――――――――――――――――――――――――――
The compounds of the present invention include plant diseases and mammals (Mammalia) that occur in vascular plants (Tracheophyta) such as pine (Pinales), magnolias, monocots, monocots (eudicots), etc. Pathogens of vertebrate (Vertebrata) infections such as birds (Aves), reptiles (Reptilia), and teleosts (Actinopterygii), plant parasitic or animal parasitic linear animals, bald animals, flat animals, protozoa, etc. Can remove the pests.

  Plant pests include Ascomycota fungi, Basidiomycota fungi, Chitridiomycota fungi, Blastocladiomycota fungi, Mucoromycotina fungi, Cercozoa fungi Cercozoa Protists, Heterokontophyta Oomycetes, Actinobacteria gram-positive fungi, Tenericutes gram-positive fungi, Proteobacteria gram-negative fungi and leaf lines Aphelenchida nematodes, Tylenchida nematodes, etc., among which the compounds of the present invention are phytopathogenic fungi belonging to the Ascomycota and Basidiomycota, leaf nematodes It exhibits excellent control effects at low concentrations against plant parasitic nematodes belonging to the order of the nematode.

  Animal pests include Ascomycota fungi, Basidiomycota fungi, Actinobacteria gram-positive fungi, Firmicutes gram-positive fungi, Tenericutes gram-positive fungi , Proteobacteria gram-negative fungi and Enoplida nematodes, Rhabditida nematodes, Strongylida nematodes, Ascaridida nematodes, rotate nematodes Spirurida nematodes, bald worms, Pseudophyllidea tapeworms, Cyclophyllidea tapeworms, Strigeidida fluke, Echinostomida flute Plasmodium (Plagiorchiida), Opisthorchiida, Amoeba, Piroplasmida, Haemosporida, Eucoccidiorida, Eucoccidiorida , Vestibuliferida ciliates, Trichomonadidae flagellates, Diplomonadida flagellates, Kinetoplastid flagellates, etc., but the compounds of the present invention are Among them, capuchin monkeys (Cebidae), rhesus monkeys (Cercopithecidae), humans (Hominidae), rabbits (Leporidae), chinchilla (Chinchillidae), guinea pigs (Caviidae), murines (Cricetidae), Muridae (Murida) ), Squiridae, Camelidae, Wild Boar (Suidae), Deer (Cervidae), Bovidae, Felidae, Canidae, Wetelidae, Mustelidae, Endoparasites of mammals (Mammalia) belonging to equidae (Equidae), kangaroo (Macropodidae), especially wild boar, bovine, feline, canine and equine feeding Enopurusu eyes which are parasitic on, show 桿線 insect eyes, circle insect eyes, the leaves wilt eyes, Hari nematode eyes, roundworm eyes, an excellent effect for combating animal parasitic nematodes belonging to the 旋尾 nematodes eyes.

  The compounds of the present invention are also effective against pests that have developed resistance to existing fungicides and nematicides, and further the compounds of the present invention are mammals, fish, crustaceans, natural enemies. It has extremely useful features that have almost no adverse effects on non-target organisms such as species and useful insects.

  When using the compound of the present invention, it is usually mixed with a suitable solid carrier or liquid carrier, and if desired, a surfactant, penetrant, spreading agent, thickener, antifreezing agent, binder, anti-caking agent. , Disintegrating agents, antifoaming agents, preservatives and anti-degradation agents, etc., and soluble concentrate, emulsion (emulsifiable concentrate), wettable powder, water-soluble powder, granular water Water dispersible granule, water soluble granule, suspension concentrate, concentrated emulsion, suspoemulsion, microemulsion, dustable powder ), Granule, tablet, and emulsifiable gel, and can be put to practical use. Further, from the viewpoint of labor saving and safety improvement, the preparations of any of the above dosage forms can be provided by being enclosed in a water-soluble package such as a water-soluble capsule and a bag of a water-soluble film.

  Examples of the solid carrier include quartz, calcite, gypsum, dolomite, chalk, kaolinite, pyrophyllite, sericite, halosite, metahalosite, kibushi clay, glazed clay, porcelain stone, siegrite, and allophane. Natural minerals such as shirasu, kira, talc, bentonite, activated clay, acid clay, pumice, attapulgite, zeolite and diatomaceous earth, for example, calcined clay, perlite, shirasu balloon, vermiculite, attapulgus clay and calcined diatomaceous earth Baked products such as magnesium carbonate, calcium carbonate, sodium carbonate, sodium bicarbonate, ammonium sulfate, sodium sulfate, magnesium sulfate, diammonium hydrogen phosphate, ammonium dihydrogen phosphate and potassium chloride, such as glucose, fructose , And Sugars such as sugar and lactose, polysaccharides such as starch, powdered cellulose and dextrin, organic materials such as urea, urea derivatives, benzoic acid and benzoic acid salts, such as wood flour, cork flour, corn cobs, walnut shells and Examples include plants such as tobacco stalks, fly ash, white carbon (for example, hydrous synthetic silica, anhydrous synthetic silica, hydrous synthetic silicate, etc.) and fertilizers.

Examples of the liquid carrier, such as xylene, alkyl (C ₉ or C _10, etc.) benzene, phenylxylylethane and alkyl (C ₁ or C _3, etc.) aromatic hydrocarbons such as naphthalene, machine oil, normal paraffin, isoparaffin and Aliphatic hydrocarbons such as naphthene, mixtures of aromatic and aliphatic hydrocarbons such as kerosene, alcohols such as ethanol, isopropanol, cyclohexanol, phenoxyethanol and benzyl alcohol, ethylene glycol, propylene glycol, diethylene glycol, hexylene glycol Polyhydric alcohols such as polyethylene glycol and polypropylene glycol, propyl cellosolve, butyl cellosolve, phenyl cellosolve, propylene glycol monomethyl ether, Ethers such as pyrene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether and propylene glycol monophenyl ether, ketones such as acetophenone, cyclohexanone and γ-butyrolactone, fatty acid methyl esters, dialkyl esters of succinic acid, dialkyl esters of glutamic acid, Esters such as adipic acid dialkyl ester and phthalic acid dialkyl ester, acid amides such as N-alkyl (C ₁ , C ₈ or C ₁₂ ) pyrrolidone, soybean oil, linseed oil, rapeseed oil, coconut oil, cottonseed oil and castor oil Oils and fats, dimethyl sulfoxide and water.

  These solid and liquid carriers may be used alone or in combination of two or more.

  Examples of the surfactant include polyoxyethylene alkyl ether, polyoxyethylene alkyl (mono or di) phenyl ether, polyoxyethylene (mono, di or tri) styryl phenyl ether, polyoxyethylene polyoxypropylene block copolymer, polyoxyethylene Ethylene fatty acid (mono or di) ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, castor oil ethylene oxide adduct, acetylene glycol, acetylene alcohol, ethylene oxide adduct of acetylene glycol, ethylene oxide adduct of acetylene alcohol and alkyl Nonionic surfactants such as glycosides, alkyl sulfate esters, alkylbenzene sulfonates, lignin sulfonates, Killsulfosuccinate, naphthalenesulfonate, alkylnaphthalenesulfonate, salt of formalin condensate of naphthalenesulfonic acid, salt of formalin condensate of alkylnaphthalenesulfonic acid, polyoxyethylene alkyl ether sulfate or phosphate ester salt, polyoxy Ethylene (mono or di) alkyl phenyl ether sulfate or phosphate ester salt, polyoxyethylene (mono, di or tri) styryl phenyl ether sulfate or phosphate ester salt, polycarboxylate (eg polyacrylate, polymaleate and Copolymers of maleic acid and olefins, etc.) and anionic surfactants such as polystyrene sulfonates, cationic surfactants such as alkylamine salts and alkyl quaternary ammonium salts, amino acid types and beties Amphoteric surfactants such as mold, and silicone-based surfactants and fluorinated surfactants.

  The content of these surfactants is not particularly limited, but is usually preferably in the range of 0.05 to 20 parts by weight with respect to 100 parts by weight of the preparation of the present invention. These surfactants may be used alone or in combination of two or more.

  The application amount of the compound of the present invention varies depending on the application scene, application time, application method, cultivated crops, etc., but generally 0.005 to 50 kg per hectare (ha) is appropriate as the amount of active ingredient.

  On the other hand, when using the compound of the present invention for controlling endoparasites of mammals and birds as domestic animals / poultry and pets, an effective amount of the compound of the present invention is administered orally together with an additive for formulation (intramuscular, Parenteral administration such as subcutaneous, intravenous, intraperitoneal; transdermal administration such as immersion, spraying, bathing, washing, pouring-on and spotting-on and dusting; nasal administration Can be administered. The compounds of the present invention can also be administered by molded products using strips, plates, bands, collars, ear marks, limb bands, labeling devices and the like. In administration, the compound of the present invention can be in any dosage form suitable for the administration route.

  Arbitrary forms to be prepared include solid preparations such as powders, granules, wettable powders, pellets, tablets, large pills, capsules, molded products containing active compounds; injection solutions, oral solutions, skin Liquid preparations used above or in body cavities; solution preparations such as pour-on, spot-on, flowable, and emulsion; semi-solid preparations such as ointments and gels.

  The solid preparation can be used mainly for oral administration or diluted with water for transdermal administration or environmental treatment. Solid preparations can be prepared by adding the active compound, if necessary, with adjuncts, mixing with appropriate excipients, and converting to the desired shape. Suitable excipients include, for example, inorganic substances such as carbonates, bicarbonates, phosphates, aluminum oxides, silicas, clays, and organic substances such as sugars, cellulose, crushed grains, and starches.

  Injection solutions can be administered intravenously, intramuscularly and subcutaneously. Injection solutions dissolve the active compound in a suitable solvent and, if necessary, solubilizers, acids, bases, buffer salts, antioxidants. And can be prepared by adding additives such as protective agents. Suitable solvents include water, ethanol, butanol, benzyl alcohol, glycerin, propylene glycol, polyethylene glycol, N-methylpyrrolidone and mixtures thereof, physiologically acceptable vegetable oils, synthetic oils suitable for injection, and the like. Examples of solubilizers include polyvinylpyrrolidone, polyoxyethylated castor oil, and polyoxyethylated sorbitan ester. Protecting agents include benzyl alcohol, trichlorobutanol, p-hydroxybenzoic acid ester and n-butanol.

  Oral solutions can be administered directly or diluted. It can be prepared in the same manner as an injectable solution.

  Flowables, emulsions, etc. can be administered directly or diluted transdermally or by environmental treatment.

  Solutions for use on the skin can be administered by dripping, spreading, rubbing, spraying, spraying or applying by dipping (dipping, bathing or washing). These solutions can be prepared in the same manner as injection solutions.

  Pour-on and spot-on agents can be dripped or sprayed onto a limited area of the skin, so that the active compound can be immersed in the skin and act systemically . Drops and drop preparations can be prepared by dissolving, suspending or emulsifying the active ingredient in suitable skin-compatible solvents or solvent mixtures. If necessary, auxiliary agents such as surfactants, colorants, absorption promoting substances, antioxidants, light stabilizers and adhesives may be added.

  Suitable solvents include water, alkanol, glycol, polyethylene glycol, polypropylene glycol, glycerin, benzyl alcohol, phenylethanol, phenoxyethanol, ethyl acetate, butyl acetate, benzyl benzoate, dipropylene glycol monomethyl ether, diethylene glycol monobutyl ether, acetone, Methyl ethyl ketone, aromatic and / or aliphatic hydrocarbons, vegetable or synthetic oil, DMF, liquid paraffin, light liquid paraffin, silicone, dimethylacetamide, N-methylpyrrolidone or 2,2-dimethyl-4-oxy-methylene-1, 3-dioxolane is mentioned. Absorption enhancers include DMSO, isopropyl myristate, dipropylene glycol pelargonate, silicone oil, aliphatic esters, triglycerides and fatty alcohols. Antioxidants include sulfites, metabisulfites, ascorbic acid, butylhydroxytoluene, butylhydroxyanisole and tocopherol.

  The emulsion can be administered orally, transdermally or as an injection. In emulsions, the active ingredient is dissolved in a hydrophobic phase or a hydrophilic phase, and this is added with a suitable emulsifier, and if necessary, a colorant, an absorption accelerator, a protective agent, an antioxidant, a light-shielding agent, a thickener Can be prepared by homogenizing with other phase solvents together with other auxiliary agents.

As hydrophobic phase (oil), paraffin oil, silicone oil, sesame oil, almond oil, castor oil, synthetic triglyceride, ethyl stearate, di-n-butyryl adipate, hexyl laurate, dipropylene glycol pelargonate, branched chain esters of saturated fatty acids shaped for short chain length fatty acids and chain length _C 16 _{-C 18,} isopropyl myristate, caprylic / capric acid esters of saturated fatty alcohols of isopropyl palmitate, chain length _C 12 _{-C 18,} isopropyl stearate Oleyl oleate, decyl oleate, ethyl oleate, ethyl lactate, waxy fatty acid ester, dibutyl phthalate, diisopropyl adipate, isotridecyl alcohol, 2-octyldodecanol, cetyl stearyl alcohol, oleyl alcohol It is below.

  Examples of the hydrophilic phase include water, propylene glycol, glycerin, and sorbitol.

  Emulsifiers include nonionic interfaces such as polyoxyethylated castor oil, polyoxyethylated sorbitan monoolefin acid, sorbitan monostearate, glyceryl monostearate, polyoxyethyl stearate, alkylphenol polyglycol ether, etc. Activators; amphoteric surfactants such as disodium N-lauryl-β-iminodipropionate and lecithin; anions such as sodium lauryl sulfate, fatty alcohol sulfate ether, monoethanolamine salt of mono / dialkyl polyglycol orthophosphate Surfactants; cationic surfactants such as cetyltrimethylammonium chloride.

  Other adjuvants include carboxymethyl cellulose, methyl cellulose, polyacrylate, alginate, gelatin, gum arabic, polyvinyl pyrrolidone, polyvinyl alcohol, methyl vinyl ether, a copolymer of maleic anhydride, polyethylene glycol, wax, colloidal silica.

  Semi-solid preparations can be administered by application on the skin or spreading or introduction into body cavities. Gels can be prepared by adding sufficient thickener to a solution prepared as described above for an injectable solution to produce a clear material having an ointment-like consistency.

  The formulation example of the case where this invention compound is used is shown below. However, the formulation examples of the present invention are not limited to these. In the following formulation examples, “parts” means parts by weight.

[Wettable powder]
Compound of the present invention 0.1-80 parts Solid carrier 5-98.9 parts Surfactant 1-10 parts Others 0-5 parts Others include, for example, anti-caking agents and decomposition inhibitors.

[Milk]
Compound of the present invention 0.1 to 30 parts Organic solvent 45 to 95 parts Surfactant 4.9 to 30 parts Water 0 to 50 parts Others 0 to 10 parts Others include, for example, spreading agents and decomposition inhibitors.

[Suspension]
Compound of the present invention 0.1 to 70 parts Liquid carrier 15 to 98.89 parts Surfactant 1 to 12 parts Others 0.01 to 30 parts Others include, for example, antifreezing agents and thickeners.

(Granule wettable powder)
Compound of the present invention 0.1 to 90 parts Solid carrier 0 to 98.9 parts Surfactant 1 to 20 parts Others 0 to 10 parts Others include, for example, binders and decomposition inhibitors.

(Liquid)
Compound of the present invention 0.01 to 70 parts Liquid carrier 20 to 99.99 parts Others 0 to 10 parts Other examples include antifreezing agents and spreading agents.

[Granule]
Compound of the present invention 0.01 to 80 parts Solid carrier 10 to 99.99 parts Others 0 to 10 parts Others include, for example, binders, decomposition inhibitors and the like.

[Dust]
Compound of the present invention 0.01 to 30 parts Solid support 65 to 99.99 parts Others 0 to 5 parts Other examples include a drift inhibitor and a decomposition inhibitor.

  Next, although the formulation example which uses this invention compound as an active ingredient is shown more concretely, this invention is not limited to these.

  In the following formulation examples, “parts” means parts by weight.

[Formulation Example 1] wettable powder Compound No. 1-003 of the present invention 20 parts pyrophyllite 74 parts Solpol 5039 4 parts (mixture of nonionic surfactant and anionic surfactant: Toho Chemical Co., Ltd.) Product name)
Carplex # 80D 2 parts (Synthetic hydrous silicic acid: Shionogi & Co., Ltd. trade name)
The above is uniformly mixed and ground to obtain a wettable powder.

[Formulation Example 2] Milk Compound of the present invention No.1-007 5 parts Xylene 75 parts N-methylpyrrolidone 15 parts Solpol 2680 5 parts (mixture of nonionic surfactant and anionic surfactant: Toho Chemical Industry (Product name)
The above is uniformly mixed to obtain an emulsion.

[Formulation Example 3] Emulsion Invention Compound No. 3-005 4 parts DBE 36 parts (mixture of dimethyl adipate, dimethyl glutarate, dimethyl succinate: trade name, manufactured by INVISTA)
Diisobutyl adipate 30 parts N-methylpyrrolidone 10 parts Soprophor BSU 14 parts (Nonionic surfactant: Rhodia trade name)
Rhodacal 70BC 6 parts (anionic surfactant: Rhodia brand name)
The above is uniformly mixed to obtain an emulsion.

[Formulation Example 4] Milk Compound of the present invention No.3-007 4 parts DBE 11 parts (mixture of dimethyl adipate, dimethyl glutarate, dimethyl succinate: trade name, manufactured by INVISTA)
Diisobutyl adipate 30 parts N-methylpyrrolidone 5 parts Soprophor BSU 14 parts (Nonionic surfactant: Rhodia trade name)
Rhodacal 70BC 6 parts (anionic surfactant: Rhodia brand name)
Propylene glycol 10 parts Water 20 parts or more are mixed uniformly to make an emulsion.

[Formulation Example 5] Suspending Agent Compound No. 1-003 25 parts Agrisol S-710 10 parts (Nonionic surfactant: trade name of Kao Corporation)
LUNOX 1000C 0.5 part (anionic surfactant: Toho Chemical Industries, Ltd. trade name)
Xanthan gum 0.2 parts water 64.3 parts After uniformly mixing the above, wet pulverize to make a suspension.

[Composition Example 6] Granule wettable powder Compound No. 1-007 of the present invention 75 parts Hytenol NE-15 5 parts (anionic surfactant: trade name of Daiichi Kogyo Seiyaku Co., Ltd.)
Vanillex N 10 parts (anionic surfactant: Nippon Paper Industries Co., Ltd. trade name)
Carplex # 80D 10 parts (Synthetic hydrous silicic acid: Shionogi Pharmaceutical Co., Ltd. trade name)
After uniformly mixing and pulverizing the above, a small amount of water is added, stirred and mixed, granulated with an extrusion granulator, and dried to obtain a granulated wettable powder.

[Formulation Example 7] Granules Invention Compound No. 3-005 5 parts Bentonite 50 parts Talc 45 parts After uniformly mixing and pulverizing the above, a small amount of water is added and mixed with stirring, and granulated with an extrusion granulator. And dried into granules.

[Formulation Example 8] Powder Compound of the present invention No.3-007 3 parts Carplex # 80D 0.5 part (Synthetic hydrous silicic acid: Shionogi Pharmaceutical Co., Ltd. trade name)
Kaolinite 95 parts Diisopropyl phosphate 1.5 parts The above is uniformly mixed and ground to obtain a powder.

  In use, each of the above preparations is diluted 1 to 20000 times with water and sprayed so that the active ingredient is 0.005 to 50 kg per hectare (ha).

[Formulation Example 9] wettable powder preparation Compound No. 1-003 of the present invention 25 parts sodium diisobutylnaphthalenesulfonate 1 part calcium n-dodecylbenzenesulfonate 10 parts alkylaryl polyglycol ether 12 parts naphthalenesulfonic acid formalin condensate Sodium salt 3 parts Emulsion type silicone 1 part Silicon dioxide 3 parts Kaolin 45 parts [Formulation Example 10] Water-soluble thickener preparation Compound No. 1-005 of the present invention 20 parts Polyoxyethylene lauryl ether 3 parts Sodium dioctyl sulfosuccinate 3. 5 parts dimethyl sulfoxide 37 parts 2-propanol 36.5 parts [Formulation Example 11] Solution for spraying the present compound No. 2-001 2 parts dimethyl sulfoxide 10 parts 2-propanol 35 parts acetone 53 parts [Formulation Example 12] transdermal Solution for administration The present compound No. 3 003 5 parts Hexylene glycol 50 parts Isopropanol 45 parts [Formulation example 13] Solution for transdermal administration Compound No. 1-003 5 parts Propylene glycol monomethyl ether 50 parts Dipropylene glycol 45 parts [Formulation example 14] Transdermal administration (Drip) Liquid Compound of the Present Invention No.1-005 2 parts Light Liquid Paraffin 98 parts [Formulation Example 15] Solution for Transdermal Administration (Drip) Compound No. 2-001 Light Liquid Paraffin 58 parts Olive Oil 30 Part ODO-H 9 parts Shin-Etsu Silicone 1 part When using the compound of the present invention as an agricultural and horticultural fungicide and nematode control agent, an effective amount of the compound of the present invention can be used alone as an active ingredient. Depending on the type of fungicide, other type of nematicide, insecticide, acaricide, plant growth regulator, herbicide, synergist, fertilizer, soil improver, etc. May be mixed during spraying.

  When the compound of the present invention is used as an endoparasite control agent, an effective amount of the compound of the present invention can be administered alone as an active ingredient, but other antibacterial agents, It can also be mixed with an anthelmintic agent at the time of preparation or administration.

  In particular, by applying mixed with other types of fungicides, other types of nematicides, other types of antibacterial agents or other types of anthelmintic agents, etc., the control spectrum can be expanded by the additive / synergistic action of the mixed agents, Effects such as improvement of pest control effect, reduction of control cost by reducing the amount of applied medicine, and sustained control effect over a longer period can be expected. In particular, mixing with other types of fungicides, nematicides, antibacterial agents and anthelmintic agents with different mechanisms of action is an extremely effective control method from the viewpoint of preventing the acquisition of drug resistance by pests. . At this time, a combination of a plurality of known fungicides, known nematodes, known insecticides, known acaricides, known antibacterial agents or known anthelmintic agents is also possible.

  As the types of fungicides, nematicides, insecticides, acaricides, anthelmintic agents or antibacterial agents used in combination with the compounds of the present invention, for example, The Pesticide Manual 16th edition, 2012, etc. Examples include the compounds described. Specific examples of common names are as follows, but the general names are not necessarily limited to these.

Fungicide:
A: Nucleic acid biosynthesis inhibitor benalaxyl, benalaxyl-M (benalaxyl-M), flaxaxyl (furalaxyl), metalaxyl (metalaxyl), metalaxyl-M (metalaxyl-M), ofurace, oxadixyl (oxadixyl),
Bupirimate, ethirimol,
Hymexazol,
B: Mitotic and mitotic inhibitors benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate-methyl,
Dietofencarb,
Ethaboxam, zoxamide,
Pencicuron (pencycuron),
Fluopicolide,
C: Respiratory inhibitor diflumetorim,
Benodanil, benzovindiflupyr, bixafen, boscalid, carboxin, fenfuram, fluopyram, flutolanil, fluxapyroxad ), Furametpyr, isofetamid, isopyrazam, mepronil, oxycarboxin, penflufen, penthiopyrad, pyraziflumid, sedaxane, sedaxane (Thifluzamide),
Azoxystrobin, coumoxystrobin, dimoxystrobin, enestrobin, enoxastrobin, famoxadone, fenamidone, phenaminestrobin ( fenaminstrobin, flufenoxystrobin, fluoxastrobin, kresoxim-methyl, mandestrobin, metminostrobin, oryastrotrobin, oryxastrobin, picoxist Robin (picoxystrobin), pyraclostrobin, pyrametostrobin, pyraoxystrobin, pyribencarb-methyl, pyriminostrobin, triclopyrical Triflopyricab, trifloxystrobin,
Amisulbrom, cyazofamid,
Dinocap, fluazinam, meptyldinocap,
Fentin, tributyltin oxide,
Silthiofam,
Ametoctradin,
D; amino acid and protein biosynthesis inhibitors cyprodinil, mepanipyrim, pyrimethanil,
Blasticidin-S,
Kasugamycin,
E; drugs that act on the signal transduction system proquinazid, quinoxyfen,
Fenpiclonil, fludioxonil,
Clozolinate, iprodione, procymidone, vinclozolin,
F: Lipid synthesis and cell membrane formation inhibitors Edifenphos, iprobenfos, isoprothiolane, pyrazophos,
Biphenyl, chloroneb, dicloran, etridiazole, quintozene, tecnazene, tolclofos-methyl,
Propamocarb hydrochloride,
Bacillus subtilis (Strain: D747, FZB24, GBO3, HAI0404, MBI600, QST713, Y1336, etc.)
G: sterol biosynthesis inhibitor azaconazole, abitertanol, bromuconazole, cyproconazole, difenoconazole, dinicoazole, dinicoazole-M (diniconazole-M), Epoxiconazole, etaconazole, fenarimol, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, Imazalil, imibenconazole, ipconazole, metconazole, microbutanil, nuarimol, oxpoconazole fumarate (oxpoc) onazole fumarate), pefurazoate, penconazole, prochloraz, propiconazole, prothioconazole, pyrifenox, pyrisoxazole, simeconazole, Tebuconazole, tetraconazole, triadimefon, triadimenol, triflumizole, triforine, triticonazole,
Aldimorph, dodemorph-acetate, fenpropidin, fenpropimorph, piperalin, spiroxamine, tridemorph,
Fenhexamid, fenpyrazamine,
H; cell wall synthesis inhibitor validamycin,
Polyoxins, polyoxins-D (polyoxorim),
Benthiavalicarb-isopropyl, dimethomorph, flumorph, iprovalicarb, mandipropamid, pyrimorph, valifenalate,
I: Melanin synthesis inhibitor phthalide, pyroquilon, tricyclazole,
Carpropamid, diclocymet, fenoxanil,
P: Plant resistance inducer acibenzolar-S-methyl,
Probenazole,
Isotianil, tiadinil,
Laminarin,
M: drugs with multiple action points Bordeaux mixture, cheshunt mixture, basic carbonate, copper carbonate, copper hydroxide, copper naphthenate , Copper oleate, copper oxychloride, copper sulfate, copper sulfate, basic, oxine copper, lime sulfur polysulfide, sulfur, amobam, ferbam, mancozeb, maneb, maneb, metiram, polycarbamate, propineb, thiram, ziram (Ziram), captan, folpet, chlorothalonil, dichlofluanid, torruf Enid (tolylfluanid), guazatine (guazatine), iminoctadine - Arubeshiru salt (iminoctadine-albesilate), iminoctadine acetate (iminoctadine-triacetate), Anirajin (anilazine), dithianon (dithianon), Kinomechioneto (chinomethionat), Furuoruimido (fluoroimide),
And U; unknown mechanism of action and other drugs Cyflufenamid, cymoxanil, diclomezine, dipymetitrone, dodine, ferimzone, flusulfamide, flutianil , Fosetyl-aluminium, metrafenone, oxathiapiproline, picarbutrazox, pyriofenone, tebufloquin, tolprocarb, triazoxide Potassium hydrogen carbonate, sodium hydrogen carbonate, shiitake mycelium extract, shiitake fruiting body extract, BCF-082 (test name), ZF-9646 (test name), and the like.

Insecticides and acaricides:
1; Acetylcholinesterase (AChE) inhibitors alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, carbaryl, carbofuran, carbofuran Fan (carbosulfan), ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, pirimicarb, thiodicarb Thiofanox, triazamate,
Acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos ( chlorpyrifos, chlorpyrifos-methyl, cyanophos, diazinon, dichlorvos, dimethoate, dimethylvinphos, disulfoton, EPN, fenitrothion (Fenitrothion), fenthion, isoxathion, malathion, methamidophos, methidathion, omethoate, oxydemeton-methy l), parathion-methyl, phenthoate, phorate, foalone, phosmet, phoxim, pirimiphos-methyl, profenofos , Prothiofos, pyraclofos, sulfopep, terbufos, tetrachlorvinphos, thiometon, trichlorfon,
2; GABAergic chloride channel antagonist endosulfan, alpha-endosulfan,
Ethiprole, fipronil, flufiprole, pyriprole,
Afoxolaner, fluralaner, rotilaner, sarolaner,
3; sodium channel modulators acrinathrin, allethrin, benfluthrin, bifenthrin, kappa-bifenthrin, bioallethrin, bioresmethrin (cycloresin), cyclothrin ), Cyfluthrin, beta-cyfluthrin, cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, cypermethrin, alpha-cypermethrin ( alpha-cypermethrin), beta-cypermethrin, zeta-cypermethrin, cyphenothrin, deltamethrin, empenthrin, espheth Esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, fluvalinate, tau-fulvalinate (tau- fluvalinate, halffenprox, heptafluthrin (heptafluthrin), imiprothrin, meperfluthrin, metofluthrin, permethrin, phenothrin, pyrethrin, pyrethrin, pyrethrin ), Silafluofen, tefluthrin, kappa-tefluthrin, tetramethrin, dT-80-phthalthrin (d-tetramethrin), tetramethylfurusuri (Tetramethylfluthrin), tralomethrin (tralomethrin), Transfluthrin (transfluthrin),
Methoxychlor,
4; Nicotinic acetylcholine receptor (nAChR) agonists acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, thiamethoxam
Sulfoxaflor,
Flupyradifurone,
5; nicotinic acetylcholine receptor (nAChR) allosteric modulators spinetoram, spinosad,
6; chloride channel activator abamectin, emamectin-benzoate, lepimectin, milbemectin,
7; juvenile hormone analog, metoprene,
Phenoxycarb,
Pyriproxyfen,
9; Pymetrozine, a hemipod selective feeding inhibitor
Flonicamid,
10; mite growth inhibitor clofentezine, hexythiazox,
Etoxazole,
11; a bacterium-derived insect midgut lining disrupter Bacillus thuringiensis (bacillus thuringiensis, subsp.israelensis, subsp.aizawai, subsp.kurstaki, subsp.tenebrionis, etc.)
12; mitochondrial ATP synthase inhibitor diafenthiuron,
Azocyclotin, fenbutatin oxide,
Propargite,
13; oxidative phosphorylation uncoupler, chlorfenapyr,
14; nicotinic acetylcholine receptor (nAChR) channel blocker bensultap, cartap, thiocyclam,
15; chitin biosynthesis inhibitor (type 0)
Bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron ), Nobifluuron, teflubenzuron, triflumuron,
16; chitin biosynthesis inhibitor (type 1)
Buprofezin,
17; molting inhibitor (fly insect)
Cyromazine,
18; molting hormone (ecdysone) receptor agonists chromafenozide, halofenozide, methoxyfenozide, tebufenozide,
19; octopamine receptor agonist amitraz,
20; Mitochondrial electron transport system complex III inhibitor hydramethylnon,
Acequinocyl,
Fluacrypyrim,
21; Mitochondrial electron transport complex I inhibitors fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad, tolfenpyrad,
Rotenone,
22; voltage-gated sodium channel blocker indoxacarb (indoxacarb), indoxacarb-MP (indoxacarb-MP),
Metaflumizone,
23; an acetyl CoA carboxylase inhibitor spirodiclofen, spiromesifen, spirotetramat,
25; Mitochondrial electron transport system complex II inhibitors cyenopyrafen, cyflumetofen,
28; ryanodine receptor modulator chlorantraniliprole, cyantraniliprole, cyclaniliprole, flubendiamide, tetraniliprole,
UN: unknown mechanism of action and other drugs azadirachtin, benzoximate, bifenazate, bromopropylate, dicohol, pyridalyl, pyrifluquinazon,
Aphidopyropen (afidopyropen), broflanilide (broflanilide), dichloromezothiaz (dicloromezotiaz), flometoquin (flumetoquin) (fluhexafon), piflubumide (pyflubumide), triflumezopyrim (triflumezopyrim) (ME 5382 (test name), NA538-89 (test name) Test name), NC-515 (test name), ZDI2501 (test name), and the like.

  Nematicides: cadusafos, dichlofenthion, etoprophos, fenamiphos, fluensulfone, fosthiazate, fostthietan, fosthietan, phosphat , Isazofos, methyl bromide, methyl isothiocyanate, oxamyl, sodium azide, tioxazafen, BYI-1921 (test name) and MAI- For example, 08015 (test name).

  Anthelmintic: acriflavine, albendazole, atovaguone, azithromycin, bithionol, bromfenofos, cambendazole, carnidazole, chloroquine chloroquine, clazuril, clindamycin hydrochloride, clorsulon, closantel, coumaphos, cymiazol, dichlorophen, dichlorophen, diethylcarbamazine, diminazen (Diminazene), disophenol, dithiazanine iodide, doxycycline hydrochloride, doramectin, emodepside, eprinomecti (eprinomecti) n), febantel, fenbendazole, flubendazole, furazolidone, glycalpyramide, imidocarb, ivermectin, levamisole, mebendazole ( mebendazole, mefloquine, melarsamine dihydrochloride (melarsamine hydrochloride), metronidazole, metyridine, milbemycin oxime, monepantel, morantel tartrate, moxidectin , Nicarbazin, niclosamide, nitroscanate, nitroxynil, omphalotin, oxantel pamoate, tartar Oxantel tartrate, oxfendazolee, oxibendazole, oxyclozanide, pamaquine, phenothiazine, piperazine adipate, piperazine citrate , Piperazine phosphate, PNU-97333 (paraherquamide A), PNU-141962 (2-deoxyparaherquamide), praziquantel, primaquine, propetamphos, propoxur, pirantel pamoate pyrantel pamoate, pyrimethamine, santonin, selamectin, sulfadimethoxine, sulfadoxine, sulfamerazine, sulphamerazine Fan monomethoxy emissions (sulfamonomethoxine), sulfamoyl dapsone (sulfamoildapsone), thiabendazole (thiabendazole), tinidazole (tinidazole), toltrazuril (toltrazuril), and tri brominated Saran (tribromsalan) and triclabendazole (triclabendazole).

  Antifungal agents: climbazole, ketoconazole and miconazole nitrate.

  Antibacterial agents: amoxicillin, ampicillin, bethoxazin, bithionol, bronopol, cefapirin, cefazolin, cefquinome, cefquinome, cefurthiofluce (Chlortetracycline), clavulanic acid, danofloxacin, difloxacin, dinitrmide, enrofloxacin, florfenicol, lincomycin, lomefoxacin ( lomefloxacin, marbofloxacin, miloxacin, milosamycin, nitrapyrin, norfloxacin, octhilinone, ofl Sacin (ofloxacin), orbifloxacin, oxolinic acid, oxytetracycline, penicillin, streptomycin, thiamphenicol, tiamulin fumarate , Tilmicosin phosphate, tyrosin phosphate, tylosin phosphate, tulathromycin, valnemulin, shell calcined calcium (calcium oxide), genus taralomyces, Trichoderma spp. And Unioniolium spp.

  Hereinafter, the present invention will be described in more detail by specifically describing synthesis examples and test examples of the compounds of the present invention as examples, but the present invention is not limited thereto.

[Synthesis example]
Synthesis example 1
N- [2- [3-Chloro-5- (trifluoromethyl) pyridin-2-yl] -2-propenyl] -2- (trifluoromethyl) benzamide (the present compound No. 1-003).

Step 1: Preparation of N- [2- [3-chloro-5- (trifluoromethyl) pyridin-2-yl] -2-propenyl] phthalimide Potassium carbonate suspended in a mixed solvent of 16 ml of toluene and 4 ml of dimethyl sulfoxide To 780 mg, phenol 531 mg was added and stirred at room temperature for 30 minutes. Next, 1.00 g of N- (2-bromo-2-propenyl) phthalimide, 1.05 g of bis (pinacolato) diborane, 158 mg of dichlorobis (triphenylphosphine) palladium (II) and 118 mg of triphenylphosphine were added to this mixture, and a nitrogen atmosphere was added. Under stirring at 50 ° C. for 3 hours. After confirming the disappearance of the raw materials, 16 ml of N, N-dimethylformamide, 1.22 g of 2,3-dichloro-5- (trifluoromethyl) pyridine and 2.50 g of potassium phosphate were added to the reaction mixture, and dichlorobis Further, 158 mg of (triphenylphosphine) palladium (II) was added, and stirring was further continued at 90 ° C. for 2 hours under a nitrogen atmosphere. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, 100 ml of water was added, and the mixture was extracted with ethyl acetate (100 ml × 2). The organic layers were combined and washed with water (50 ml × 1), then dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the remaining solid was washed with diisopropyl ether to give 0.66 g of the desired product. Was obtained as pale yellow crystals.
Melting point: 147.0-150.0 ° C
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.72 (s, 1H), 7.95 (s, 1H), 7.8-7.9 (m, 2H), 7.7-7.75 (m, 2H), 5.73 (s , 1H), 5.71 (s, 1H), 4.78 (s, 2H).

Step 2: Preparation of N- [2- [3-chloro-5- (trifluoromethyl) pyridin-2-yl] -2-propenyl] -2- (trifluoromethyl) benzamide N- [2- [3- To a solution of 500 mg of chloro-5- (trifluoromethyl) pyridin-2-yl] -2-propenyl] phthalimide in 5 ml of toluene was added 1.06 g of a 40% aqueous methylamine solution, and the mixture was stirred at room temperature for 20 hours. After completion of the reaction, a 10% aqueous hydrochloric acid solution was added to the reaction mixture until the aqueous phase became acidic and washed with toluene. The obtained aqueous layer was made basic by adding sodium carbonate, extracted with ethyl acetate (15 ml × 2), the organic layer was washed with water (10 ml × 1), dehydrated in the order of saturated brine and then anhydrous sodium sulfate. The solvent was distilled off under drying and reduced pressure. The residue was dissolved in 10 ml of dichloromethane, 81 mg of triethylamine was added, 142 mg of 2- (trifluoromethyl) benzoyl chloride was added dropwise with stirring under ice cooling, and the stirring was continued for another 30 hours at the end of the dropwise addition. After completion of the reaction, the solvent was distilled off under reduced pressure, and 10 ml of water was added to the residue, followed by extraction with ethyl acetate (10 ml × 2). The organic layers were combined and washed with water (10 ml × 1), dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (3: 7 to 5: 5 gradient) to obtain 86 mg of the desired product as white crystals.
Melting point 91.0-92.0 ° C
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.71 (s, 1H), 8.00 (s, 1H), 7.45-7.7 (m, 4H), 6.44 (bs, 1H), 5.99 (s, 1H ), 5.92 (s, 1H), 4.54 (d, J = 5.4Hz, 2H).

Synthesis example 2
N- [2- (5-Bromo-3-chloropyridin-2-yl) -2-propenyl] -2- (trifluoromethyl) benzamide (the present compound No. 1-002).

Step 1; Preparation of 1- (5-bromo-3-chloropyridin-2-yl) ethanone To a 15 ml toluene solution of 3.0 g of 5-bromo-3-chloropyridin-2-carbonitrile was stirred under ice-cooling and methylation. 4.8 ml of a 3M solution of magnesium bromide in diethyl ether was added dropwise and stirred at the same temperature for 0.5 hours. After completion of the reaction, the reaction mixture was poured into 20 ml of 4N hydrochloric acid under ice-cooling and extracted with toluene (30 ml × 2). The organic layers were combined, dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 2.7 g of a crude desired product as brown crystals. This was directly used in the next step without further purification.
Melting point: 78.0-79.0 ° C
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 8.58 (d, J = 1.8 Hz, 1H), 7.97 (d, J = 1.8 Hz, 1H), 2.67 (s, 3H).

Step 2: Preparation of 2-bromo-1- (5-bromo-3-chloropyridin-2-yl) ethanone 1- (5-Bromo-3-chloropyridin-2-yl) ethanone in 1.60 g of toluene in 8 ml solution To the solution, 5.5 ml of a 30% hydrobromic acetic acid solution was added, and 1.28 g of bromine was added dropwise with stirring on ice. After stirring at room temperature for 18 hours, 0.62 g of bromine was added, and after another 2.5 hours, 0.31 g of bromine was added again, and stirring was continued for another 3 hours. After completion of the reaction, 50 ml of water was added to the reaction mixture and extracted with toluene (50 ml × 2). The organic layers were combined and washed with 100 ml of water and then with 100 ml of a saturated aqueous sodium hydrogen sulfite solution, then dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. 20 ml of heptane was added to the residue and the mixture was stirred for 30 minutes under ice cooling. The precipitated solid was separated by filtration to obtain 1.7 g of the desired product as white crystals.
Melting point: 58.0-62.0 ° C
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 8.60 (d, J = 2.1 Hz, 1H), 8.02 (d, J = 2.1 Hz, 1H), 4.76 (s, 2H).

Step 3: Production of N- [2- (5-bromo-3-chloropyridin-2-yl) -2-oxoethyl] phthalimide 2-bromo-1- (5- A solution of 5.1 g of bromo-3-chloropyridin-2-yl) ethanone in 20 ml of dimethyl sulfoxide was added dropwise. After completion of the reaction, 50 ml of water was added to the reaction mixture and extracted with ethyl acetate (100 ml × 2). The organic layers were combined and washed with water (100 ml × 1), dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 4.5 g of a crude target product as yellow crystals. This was directly used in the next step without further purification.
Melting point: 62.0-68.0 ° C
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.67 (d, J = 1.8 Hz, 1H), 8.03 (d, J = 1.8 Hz, 1H), 7.7-7.95 (m, 4H), 5.28 ( s, 2H).

Step 4; Preparation of N- [2- (5-bromo-3-chloropyridin-2-yl) -2-propenyl] phthalimide N- [2- (5-Bromo-3-chloropyridin-2-yl)- To a solution of 2.20 g of 2-oxoethyl] phthalimide, 2.34 g of methyltriphenylphosphonium iodide and 0.01 g of crown ether (18-crown-6) in 100 ml of toluene was added 0.65 g of potassium tert-butoxide and heated under reflux. And stirred. After 4 hours, 2.34 g of methyltriphenylphosphonium iodide and 0.65 g of potassium tert-butoxide were added to the reaction mixture, and stirring was continued for another hour under heating and refluxing. After completion of the reaction, the solvent was distilled off under reduced pressure, 200 ml of water and 200 ml of ethyl acetate were added to the residue, and the organic layer was separated. The organic layer was washed with water (50 ml × 1), dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (1: 9-2: 8 gradient) to obtain 0.83 g of the objective product as yellow crystals.
Melting point: 63.0-67.0 ° C
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.50 (d, J = 2.1 Hz, 1H), 7.87 (d, J = 2.1 Hz, 1H), 7.65-7.9 (m, 4H), 5.66 ( s, 1H), 5.63 (s, 1H), 4.73 (s, 2H).

Step 5; Preparation of 2- (5-bromo-3-chloropyridin-2-yl) -2-propenylamine N- [2- (5-Bromo-3-chloropyridin-2-yl) -2-propenyl] To a solution of 830 mg of phthalimide in 8 ml of toluene and 0.5 ml of ethanol, 1.70 g of 40% aqueous methylamine solution was added with stirring under ice cooling, and the mixture was stirred at room temperature for 8 hours. After completion of the reaction, 10 ml of water was added to the reaction mixture, and concentrated hydrochloric acid was added dropwise with stirring under ice cooling until the pH reached 1. The aqueous layer was separated, sodium carbonate was added until the pH was 13-14, and the mixture was extracted with ethyl acetate (50 ml × 2). The organic layers were combined, dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 280 mg of the crude desired product as a yellow oily substance. This was directly used in the next step without further purification.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.5-8.6 (m, 1H), 7.85-7.95 (m, 1H), 5.65 (s, 1H), 5.49 (s, 1H), 3.71 (s , 2H).

Step 6: Preparation of N- [2- (5-bromo-3-chloropyridin-2-yl) -2-propenyl] -2- (trifluoromethyl) benzamide 2- (5-Bromo-3-chloropyridine- To a solution of 280 mg of 2-yl) -2-propenylamine and 228 mg of triethylamine in 3 ml of dichloromethane, 283 mg of 2- (trifluoromethyl) benzoyl chloride was added dropwise with stirring under ice-cooling, and the mixture was further stirred at room temperature for 1.5 hours. Continued. After completion of the reaction, 15 ml of water was added to the reaction mixture, followed by extraction with dichloromethane (20 ml × 1). The organic layer was dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (1: 9) to obtain 240 mg of the desired product as pale yellow crystals.
Melting point: 49.0-53.0 ° C
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.50 (d, J = 2.1 Hz, 1H), 7.93 (d, J = 2.1 Hz, 1H), 7.45-7.7 (m, 4H), 6.43 ( bs, 1H), 5.90 (s, 1H), 5.83 (s, 1H), 4.49 (d, J = 5.7 Hz, 2H).

Synthesis example 3
(E) -N- [3-chloro-2- (3,5-dichloropyridin-2-yl) -2-propenyl] -2- (trifluoromethyl) benzamide (the present compound No. 1-004) and (Z) -N- [3-chloro-2- (3,5-dichloropyridin-2-yl) -2-propenyl] -2- (trifluoromethyl) benzamide (the present compound No. 1-005).

Step 1: Preparation of N- [3-chloro-2- (3,5-dichloropyridin-2-yl) -2-propenyl] phthalimide N- [2- (3,5-dichloropyridin-2-yl)- To a solution of 2.0 g of 2-oxoethyl] phthalimide, 2.1 g of chloromethyltriphenylphosphonium chloride and 0.01 g of crown ether (18-crown-6) in 130 ml of toluene was added 0.67 g of potassium tert-butoxide and heated under reflux. And stirred. After 2.5 hours, 2.1 g of chloromethyltriphenylphosphonium chloride and 0.67 g of potassium tert-butoxide were added to the reaction mixture, and stirring was further continued under heating and reflux for 40 minutes. After completion of the reaction, the solvent was distilled off under reduced pressure, 200 ml of water and 200 ml of ethyl acetate were added to the residue, and the organic layer was separated. The organic layer was dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (1: 9) to obtain 1.2 g of the desired product as a yellow resinous substance.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.43 and 8.32 (d, J = 2.1 Hz, 1H), 7.6-7.9 (m, 5H), 6.77 and 6.58 (s, 1H), 4.95 and 4.64 (s, 2H).

Step 2: Preparation of 3-chloro-2- (3,5-dichloropyridin-2-yl) -2-propenylamine N- [3-Chloro-2- (3,5-dichloropyridin-2-yl)- To a solution of 2-propenyl] phthalimide 350 mg in toluene 3 ml was added 40% methylamine aqueous solution 740 mg and stirred at room temperature for 15 hours. After completion of the reaction, 10 ml of water was added to the reaction mixture, and concentrated hydrochloric acid was added dropwise with stirring under ice cooling until the pH reached 1. The aqueous layer was separated, sodium carbonate was added until the pH was 13-14, and the mixture was extracted with ethyl acetate (50 ml × 1). The organic layer was dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 130 mg of the crude target product as a yellow oil. This was directly used in the next step without further purification.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.52 and 8.46 (d, J = 2.1 Hz, 1H), 7.79 and 7.76 (d, J = 2.1 Hz, 1H), 6.52 and 6.46 (s, 1H ), 3.87 and 3.67 (s, 2H).

Step 3; (E) -N- [3-chloro-2- (3,5-dichloropyridin-2-yl) -2-propenyl] -2- (trifluoromethyl) benzamide and (Z) -N- [ Preparation of 3-chloro-2- (3,5-dichloropyridin-2-yl) -2-propenyl] -2- (trifluoromethyl) benzamide 3-chloro-2- (3,5-dichloropyridine-2- Yl) -2-propenylamine (120 mg) and triethylamine (152 mg) in dichloromethane (3 ml) was added dropwise with ice-cooling and stirring, and 2- (trifluoromethyl) benzoyl chloride (127 mg) was added dropwise. After completion of the reaction, 10 ml of water was added to the reaction mixture, followed by extraction with dichloromethane (10 ml × 1). The organic layer was dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (3:17) to obtain 41 mg (E-isomer) of yellow resinous material and 75 mg (Z-isomer) of yellow crystals. .
E-isomer;
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.43 (d, J = 2.4 Hz, 1H), 7.87 (d, J = 2.4 Hz, 1H), 7.4-7.7 (m, 4H), 6.75 ( s, 1H), 6.27 (bs, 1H), 4.71 (d, J = 6.0Hz, 2H).
Z-isomer;
Melting point: 10.0-103.0 ° C
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 8.49 (d, J = 2.1 Hz, 1H), 7.81 (d, J = 2.1 Hz, 1H), 7.4-7.75 (m, 4H), 6.66 ( s, 1H), 6.24 (bs, 1H), 4.43 (d, J = 4.8 Hz, 2H).

  This invention compound can be manufactured according to the said manufacturing method and an Example. Examples of N-alkenyl-substituted amide compounds included in the present invention produced in the same manner as in Synthesis Example 1 to Synthesis Example 3 are shown in Tables 3 to 9, and examples of their production intermediates are shown in Table 10 to As shown in Table 12, the N-alkenyl-substituted amide compounds and their production intermediates included in the present invention are not limited to these.

In the table, “* 1” in the melting point column means that the property of the compound was oily or resinous.
Table 3

――――――――――――――――――――――――――――――――――――――――
No. R ³ R ¹ R ² Y ¹ Y ² Y ³ Y ⁴ mp (° C)
――――――――――――――――――――――――――――――――――――――――
1-001 HHH Cl H Cl H * 1
1-002 HHH Cl H Br H 49.0-53.0
1-003 HHH Cl H CF ₃ H 91.0-92.0
1-004 H Cl H Cl H Cl H * 1
1-005 HH Cl Cl H Cl H 100.0-103.0
1-006 H CH ₃ H Cl H Cl H * 1
1-007 HH CH ₃ Cl H Cl H 80.0-82.0
1-008 H OCH ₃ H Cl H Cl H * 1
1-009 HH OCH ₃ Cl H Cl H * 1
――――――――――――――――――――――――――――――――――――――――
Table 4

――――――――――――――――――――――――――――――――――――――――
No. X ¹ R ³ R ¹ R ² Y ¹ Y ² Y ³ Y ⁴ mp (℃)
――――――――――――――――――――――――――――――――――――――――
2-001 CF ₃ HHH Cl H Cl H 48.0-52.0
――――――――――――――――――――――――――――――――――――――――
Table 5

――――――――――――――――――――――――――――――――――――――――
No. X ¹ R ³ R ¹ R ² Y ¹ Y ² Y ³ Y ⁴ mp (℃)
――――――――――――――――――――――――――――――――――――――――
3-001 Cl HHH Cl H Cl H 59.0-61.0
3-002 CHF ₂ HHH Cl H Cl H 56.0-60.0
3-003 CF ₃ HHH Cl H Cl H 76.0-80.0
3-004 CHF ₂ H Cl H Cl H Cl H * 1
3-005 CHF ₂ HH Cl Cl H Cl H 46.0-50.0
3-006 CHF ₂ H CH ₃ H Cl H Cl H * 1
3-007 CHF ₂ HH CH ₃ Cl H Cl H * 1
――――――――――――――――――――――――――――――――――――――――
Table 6

――――――――――――――――――――――――――――――――――――――――
No. X ¹ R ³ R ¹ R ² Y ¹ Y ² Y ³ Y ⁴ mp (℃)
――――――――――――――――――――――――――――――――――――――――
4-001 CF ₃ HHH Cl H Br H 97.0-98.0
――――――――――――――――――――――――――――――――――――――――
Table 7

――――――――――――――――――――――――――――――――――――――――
No. X ¹ R ³ R ¹ R ² Y ¹ Y ² Y ³ Y ⁴ mp (℃)
――――――――――――――――――――――――――――――――――――――――
5-001 CH ₃ HHH Cl H CF ₃ H 100.0-101.0
――――――――――――――――――――――――――――――――――――――――
Table 8

――――――――――――――――――――――――――――――――――――――――
No. X ¹ R ³ R ¹ R ² Y ¹ Y ² Y ³ Y ⁴ mp (℃)
――――――――――――――――――――――――――――――――――――――――
5-001 CHF ₂ HHH Cl H Cl H * 1
5-002 CHF ₂ H Cl H Cl H Cl H * 1
5-003 CHF ₂ HH Cl Cl H Cl H 36.0-37.0
5-004 CHF ₂ H CH ₃ H Cl H Cl H * 1
5-005 CHF ₂ HH CH ₃ Cl H Cl H * 1
――――――――――――――――――――――――――――――――――――――――
Table 9

――――――――――――――――――――――――――――――――――――――――
No. X ¹ R ³ R ¹ R ² Y ¹ Y ² Y ³ Y ⁴ mp (℃)
――――――――――――――――――――――――――――――――――――――――
7-001 CHF ₂ HHH Cl H Cl H * 1
7-002 CF ₃ HHH Cl H Cl H 67.0-71.0
7-003 CHF ₂ H CH ₃ H Cl H Cl H * 1
7-004 CHF ₂ HH CH ₃ Cl H Cl H * 1
――――――――――――――――――――――――――――――――――――――――
Table 10

――――――――――――――――――――――――――――――――――――――――
No. R ³ R ¹ R ² Y ¹ Y ² Y ³ Y ⁴ mp (° C)
――――――――――――――――――――――――――――――――――――――――
8-001 HHH Cl H Cl H * 1
8-002 H [H, Cl] Cl H Cl H * 1
8-003 HHH Cl H Br H * 1
――――――――――――――――――――――――――――――――――――――――
The above description of [H, Cl] means a mixture of geometric isomers with the substituents R ¹ and R ² .
Table 11

――――――――――――――――――――――――――――――――――――――――
No. R ³ R ¹ R ² Y ¹ Y ² Y ³ Y ⁴ mp (° C)
――――――――――――――――――――――――――――――――――――――――
9-001 HHH Cl H Cl H 75.0-79.0
9-002 H [H, Cl] Cl H Cl H * 1
9-003 H [H, CH ₃ ] Cl H Cl H 46.0-51.0
9-004 HHH Cl H Br H 63.0-67.0
――――――――――――――――――――――――――――――――――――――――
The above description of [H, Cl] and [H, CH ₃ ] means a mixture of geometric isomers with the substituents R ¹ and R ² .
Table 12

――――――――――――――――――――――――――――――――――――――――
No. R ³ R ¹ R ² Y ¹ Y ² Y ³ Y ⁴ mp (° C)
――――――――――――――――――――――――――――――――――――――――
10-001 HHH Cl H Br H * 1
10-002 H [H, Cl] Cl H Br H * 1
――――――――――――――――――――――――――――――――――――――――
The above description of [H, Cl] means a mixture of geometric isomers with the substituents R ¹ and R ² .

Of the compounds in Tables 3 to 11, ¹ H NMR data of compounds having no melting point in the table are shown in Table 12.
Table 12 ―――――――――――――――――――――――――――――――――――――――
No. ¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz)
―――――――――――――――――――――――――――――――――――――――
1-001 δ8.41 (d, J = 2.1Hz, 1H), 7.77 (d, J = 2.1Hz, 1H), 7.4-7.7 (m, 4H),
6.42 (bs, 1H), 5.89 (s, 1H), 5.81 (s, 1H), 4.49 (d, J = 6.0Hz, 2H).
1-004 δ8.43 (d, J = 2.4Hz, 1H), 7.78 (d, J = 2.4Hz, 1H), 7.4-7.7 (m, 4H),
6.75 (s, 1H), 6.27 (bs, 1H), 4.71 (d, J = 6.0Hz, 2H).
1-006 δ8.36 (d, J = 2.1Hz, 1H), 7.75 (d, J = 2.1Hz, 1H), 7.4-7.7 (m, 4H),
6.52 (bs, 1H), 6.28 (q, J = 6.6Hz, 1H), 4.49 (d, J = 5.4Hz, 2H),
2.03 (d, J = 6.6Hz, 3H).
1-008 δ8.37 (d, J = 2.4Hz, 1H), 7.71 (d, J = 2.4Hz, 1H), 7.4-7.7 (m, 4H),
6.92 (s, 1H), 6.45 (bs, 1H), 4.55 (d, J = 5.4Hz, 2H), 3.83 (s, 3H).
1-009 δ8.39 (d, J = 2.1Hz, 1H), 7.74 (d, J = 2.1Hz, 1H), 7.45-7.7 (m, 4H),
6.62 (bs, 1H), 6.57 (s, 1H), 4.27 (d, J = 5.1Hz, 2H), 3.73 (s, 3H).
3-004 δ8.73 (dd, J = 4.8, 1.8Hz, 1H), 8.44 (d, J = 2.1Hz, 1H), 7.8-7.9 (m, 1H),
7.80 (d, J = 2.1Hz, 1H), 7.46 (dd, J = 7.8, 4.8Hz, 1H),
6.87 (t, J = 54.3Hz, 1H), 6.79 (s, 1H), 6.61 (bs, 1H),
4.72 (d, J = 6.0Hz, 2H).
3-006 δ8.74 (dd, J = 4.8, 1.8Hz, 1H), 8.38 (d, J = 2.1Hz, 1H), 7.8-7.95 (m, 1H),
7.76 (d, J = 2.1Hz, 1H), 7.45 (dd, J = 7.8, 4.8Hz, 1H),
6.93 (t, J = 54.6Hz, 1H), 6.85 (bs, 1H), 6.28 (q, J = 7.2Hz, 1H),
4.50 (d, J = 5.4Hz, 2H), 2.03 (d, J = 7.2Hz, 3H).
3-007 δ8.75 (dd, J = 4.8, 1.8Hz, 1H), 8.48 (d, J = 2.1Hz, 1H), 7.8-7.9 (m, 1H),
7.80 (d, J = 2.1Hz, 1H), 7.46 (dd, J = 7.8, 4.8Hz, 1H),
6.96 (t, J = 54.3Hz, 1H), 6.55 (bs, 1H), 6.11 (q, J = 6.9Hz, 1H),
4.36 (d, J = 5.4Hz, 2H), 1.55 (d, J = 6.9Hz, 3H).
6-001 δ8.44 (d, J = 2.1Hz, 1H), 7.89 (s, 1H), 7.75 (d, J = 2.1Hz, 1H),
6.86 (bs, 1H), 6.78 (t, J = 54.6Hz, 1H), 5.81 (s, 1H), 5.75 (s, 1H),
4.45 (d, J = 5.7Hz, 2H), 3.91 (s, 3H).
6-002 δ8.44 (d, J = 2.1Hz, 1H), 7.85 (s, 1H), 7.74 (d, J = 2.1Hz, 1H),
6.72 (t, J = 54.3Hz, 1H), 6.65-6.8 (m, 2H), 4.68 (d, J = 6.0Hz, 2H),
3.89 (s, 3H).
6-004 δ8.41 (d, J = 2.1Hz, 1H), 7.85 (s, 1H), 7.72 (d, J = 2.1Hz, 1H),
6.86 (bs, 1H), 6.77 (t, J = 54.6Hz, 1H), 6.22 (q, J = 7.2Hz, 1H),
4.46 (d, J = 5.4Hz, 2H), 3.90 (s, 3H), 1.99 (d, J = 7.2Hz, 3H).
6-005 δ8.49 (d, J = 2.1Hz, 1H), 7.83 (s, 1H), 7.76 (d, J = 2.1Hz, 1H),
6.82 (t, J = 54.0Hz, 1H), 6.56 (bs, 1H), 6.04 (q, J = 7.2Hz, 1H),
4.31 (d, J = 5.1Hz, 2H), 3.91 (s, 3H), 1.54 (d, J = 7.2Hz, 3H).
7-001 δ8.45 (d, J = 2.1Hz, 1H), 7.78 (d, J = 2.1Hz, 1H), 7.14 (t, J = 54.6Hz, 1H),
7.01 (bs, 1H), 5.86 (s, 1H), 5.83 (s, 1H), 4.42 (d, J = 5.7Hz, 2H),
2.73 (s, 3H).
7-003 δ8.42 (d, J = 2.1Hz, 1H), 7.77 (d, J = 2.1Hz, 1H), 7.16 (t, J = 54.0Hz, 1H),
7.10 (bs, 1H), 6.27 (q, J = 7.2Hz, 1H), 4.43 (d, J = 5.4Hz, 2H),
2.74 (s, 3H), 2.01 (d, J = 7.2Hz, 3H).
7-004 δ8.49 (d, J = 2.1Hz, 1H), 7.79 (d, J = 2.1Hz, 1H), 7.18 (t, J = 54.3Hz, 1H),
6.65 (bs, 1H), 6.08 (q, J = 6.9Hz, 1H), 4.28 (d, J = 5.1Hz, 2H),
2.75 (s, 3H), 1.55 (d, J = 6.9Hz, 3H).
8-001 δ8.45 (d, J = 2.1Hz, 1H), 7.75 (d, J = 2.1Hz, 1H), 5.64 (d, J = 0.6Hz, 1H),
5.47 (d, J = 0.6Hz, 1H), 3.71 (s, 2H).
―――――――――――――――――――――――――――――――――――――――
[Test example]
Next, the usefulness of the compound of the present invention as a pest control agent will be specifically described in the following test examples, but the present invention is not limited to these.

  Preparation of test drug solution A: Emulsified white sample of the present compound (Solpol (registered trademark) 3005XL (manufactured by Toho Chemical Industry): N-methylpyrrolidone: Solvesso (registered trademark) 200 (manufactured by ExxonMobil)) = 1: 5: 2 mixture ) To give a 20% concentrated emulsion. Next, distilled water was added to dilute to a predetermined concentration (500 ppm), and this chemical solution was used in Test Examples 1 to 8 below.

  Preparation of test drug solution B: The compound of the present invention was dissolved in dimethyl sulfoxide to prepare a 1% strength solution. Next, distilled water was added to dilute to a predetermined concentration (100 ppm), and this chemical solution was used in Test Examples 9 to 13 below.

Test Example 1 Cucumber powdery mildew prevention effect test Cucumber (variety: Sagamihanjiro) was planted in a 90 cm ³ plastic pot, and 5 ml of test chemical solution A of the present compound was sprayed per pot at the cotyledon stage. After air drying, the cucumber was placed in an air-conditioned greenhouse (20 ° C.) and sprayed with a conidial spore suspension of cucumber powdery mildew (Erysiphe polygoni, Synonym; Erysiphe betae). After 9 days at the same temperature, the proportion of the lesions formed in the inoculated leaves was measured, and the control value was calculated according to the following formula. In addition, the test was performed by 2 continuous systems.

Control value = [1- (treatment area lesion area ratio / non-treatment area lesion area ratio)] × 100
As a result, among the tested compounds, the following compounds showed a control value of 70% or more.
Compound of the present invention: No.1-001,1-003,1-005,1-006,1-007,1-008,1-009,3-002,3-004,3-005,3-006, 3-007,5-001,6-001,6-003,6-005,7-001,7-002,7-004.

Test example 2 Cucumber gray mold prevention effect test (spore inoculation)
Cucumber (variety: Sagamihanjiro) was planted in a 90 cm ³ plastic pot, and 5 ml of test chemical solution A of the present compound was sprayed per pot at the cotyledon stage. After air drying, the treated leaves were cut out and placed in a plastic container. A conidial spore suspension of cucumber gray mold fungus (Botrytis cinerea) and a dissolved PDA medium were mixed at a ratio of 1: 1, and 30 μl of the treated leaves were inoculated dropwise. After inoculation, after placing it at 20 ° C. under high humidity for 3 days, the ratio of the formed lesions to the inoculated leaves was measured, and the control value was calculated from the same formula as in Test Example 1. In addition, the test was performed by 2 continuous systems.

As a result, among the tested compounds, the following compounds showed a control value of 70% or more.
Compound of the present invention: No.1-001,1-002,1-003,1-004,1-005,1-006,1-007,1-008,1-009,2-001,3-001, 3-002,3-003,3-004,3-005,3-006,3-007,5-001,6-001,6-002,6-003,6-004,6-005,7- 001,7-002,7-003,7-004.

Test example 3 Cucumber gray mold prevention effect test (mycelia inoculation)
Cucumber (variety: Sagamihanjiro) was planted in a 90 cm ³ plastic pot, and 5 ml of test chemical solution A of the present compound was sprayed per pot at the cotyledon stage. One day later, the pot was placed in a plastic container and inoculated into a cucumber cotyledon treated with a drug containing bacterial agar pieces (diameter 5 mm) of cucumber gray mold (Botrytis cinerea) previously cultured in PDA medium. After inoculation, the plastic container is covered with plastic, humidified, and left at 20 ° C for 2 days. Then, the proportion of the lesions formed in the inoculated leaves is measured, and the control value is calculated from the same formula as in Test Example 1. did. In addition, the test was performed by 2 continuous systems.

As a result, among the tested compounds, the following compounds showed a control value of 70% or more.
Compound of the present invention: No.1-001,1-002,1-003,1-004,1-005,1-006,1-007,1-008,1-009,2-001,3-001, 3-002,3-003,3-004,3-005,3-006,3-007,5-001,6-001,6-002,6-003,6-004,6-005,7- 001,7-002,7-004.

Test Example 4 Cucumber Nuclear Disease Prevention Effect Test Cucumber (variety: Sagamihanjiro) was planted in a 90 cm ³ plastic pot, and 5 ml of test chemical solution A of the present compound was sprayed per pot at the cotyledon stage. After air-drying, the pot was placed in a plastic container and inoculated into a cucumber cotyledon treated with a drug, a garnish containing agar (Sclerotinia sclerotiorum) -containing agar pieces (diameter 5 mm) previously cultured in a PDA medium. After inoculation, the plastic container is covered with plastic, humidified, and left at 20 ° C for 2 days. Then, the proportion of the lesions formed in the inoculated leaves is measured, and the control value is calculated from the same formula as in Test Example 1. did. In addition, the test was performed by 2 continuous systems.

As a result, among the tested compounds, the following compounds showed a control value of 70% or more.
Compound of the present invention: No.1-001,1-002,1-003,1-004,1-005,1-006,1-007,1-008,1-009,2-001,3-001, 3-002,3-003,3-004,3-005,3-006,3-007,5-001,6-001,6-002,6-003,6-004,6-005,7- 001,7-002,7-003,7-004.

Test Example 5 Cucumber Anthrax Prevention Effect Test Cucumber (variety: Sagamihanjiro) was planted in a 90 cm ³ plastic pot, and 5 ml of test chemical solution A of the present compound was sprayed per pot at the cotyledon stage. One day later, a conidial spore suspension of cucumber anthracnose fungus (Colletotrichum lagenarium, Synonym; Colletotrichum orbiculare) was spray-inoculated and placed in an inoculation box at a temperature of 25 ° C. and a humidity of 100% for 2 days. Then, after placing it in an air-conditioned greenhouse (23 ° C.) for 7 days at the same temperature, the proportion of the formed lesions in the inoculated leaves was measured, and the control value was calculated from the same calculation formula as in Test Example 1. . In addition, the test was performed by 2 continuous systems.

As a result, among the tested compounds, the following compounds showed a control value of 70% or more.
This invention compound: No.1-006,3-002,3-004,3-005,3-006,6-005,7-003.

Test Example 6 Wheat powdery mildew prevention effect test 1.3 ml of test chemical solution A of the present invention was sprayed to a 90 cm ³ plastic pot planted with 1.3 leaves of wheat (variety: Norin 61). One day after spraying, the pot was placed in an air-conditioned greenhouse (20 ° C.), and wheat was inoculated with conidia of wheat powdery mildew (Blumeria graminis f. Sp. Tritici). Thereafter, it was held for 7 days, the ratio of the formed lesions to the inoculated leaves was measured, and the control value was calculated from the same formula as in Test Example 1. In addition, the test was performed by 2 continuous systems.

As a result, among the tested compounds, the following compounds showed a control value of 70% or more.
Compound of the present invention: No.1-001,1-002,1-003,1-004,1-005,1-006,1-007,1-008,1-009,2-001,3-001, 3-002,3-003,3-004,3-005,3-006,3-007,5-001,6-001,6-002,6-003,6-004,6-005,7- 001,7-002,7-003,7-004.

Test Example 7 Wheat Blight Prevention Effect Test 1.3 5 ml of test chemical solution A of the present invention was sprayed per pot into a 90 cm ³ plastic pot planted with wheat (variety: Haruyutaka) at the ^3- leaf stage. One day after spraying, a conidial spore suspension of wheat blight fungus (Phaeosphaeria nodorum, Synonym; Septoria nodorum) was spray-inoculated on wheat and placed in an inoculation box at a temperature of 20 ° C. and a humidity of 100% for 2 days. Thereafter, it was placed in an air-conditioned greenhouse (20 ° C.) and held for 6 days. The ratio of the formed lesions to the inoculated leaves was measured, and the control value was calculated from the same calculation formula as in Test Example 1. In addition, the test was performed by 2 continuous systems.

As a result, among the tested compounds, the following compounds showed a control value of 70% or more.
The present compound: No.1-001,1-003,1-007,3-002,3-003,3-005,3-007,7-001,7-002,7-004.

Test Example 8 Wheat Red Rust Prevention Effect Test 1.3 ml of test chemical solution A of the present invention was sprayed to a 90 cm ³ plastic pot planted with 1.3 leaves of wheat (variety: Norin 61). One day after spraying, the spore suspension of wheat rust (Puccinia recondita) was spray-inoculated on wheat and placed in an inoculation box at a temperature of 20 ° C. and a humidity of 100% for 1 day. Thereafter, it was placed in an air-conditioned greenhouse (20 ° C.) and held for 8 days. The ratio of the formed lesions to the inoculated leaves was measured, and the control value was calculated from the same calculation formula as in Test Example 1. In addition, the test was performed by 2 continuous systems.

As a result, among the tested compounds, the following compounds showed a control value of 70% or more.
The compound of the present invention: No. 3-004, 6-002, 7-002, 7-003.

Test Example 9 Antibacterial activity test against Aspergillus oryzae After dispensing 60 μl of potato dextrose 1% agar medium to a 96-well plate, sterile water containing Aspergillus niger spores (10 spores / 3 μl) was added. 30 μl was added per well. From this, 10 μl of test drug solution B of the compound of the present invention was added to each well and allowed to stand at 25 ° C. under dark conditions. The bacterial flora area ratio (%) 2 days after the addition of the drug was determined, and the efficiency (%) for the untreated area was calculated by the following formula.

Efficacy (%) = [1- (processed microbial flora area ratio / untreated ward flora area ratio)] × 100
As a result, among the tested compounds, the following compounds showed an efficiency (%) of 50% or more.
Compound of the present invention: No.1-001,1-002,1-003,1-004,1-005,1-006,1-007,2-001,3-002,3-003,3-005, 5-001,6-001,6-003,6-004,6-005,7-001,7-002,7-003,7-004.

Test Example 10 Insecticidal test against sweet potato nematode After dispensing 60 μl of potato dextrose 1% agar medium into a 96-well plate, each well was given sterile water (10 eggs / 3 μl) containing eggs of sweet potato nematode (Meloidogyne incognita). 30 μl per dose was added. From this, 10 μl of test drug solution B of the compound of the present invention was added to each well and allowed to stand at 25 ° C. under dark conditions. The number of unhatched eggs and the number of inactive larvae 4 days after the addition of the drug were counted, and the efficiency (%) for the untreated group was calculated by the following equation.

Efficacy (%) = [(number of untreated eggs treated + number of inactive larvae) / number of untreated group active larvae] x 100
As a result, among the tested compounds, the following compounds showed an efficiency (%) of 50% or more.
Compound of the present invention: No.1-001,1-002,1-003,1-004,1-005,1-006,1-007,1-008,1-009,2-001,3-001, 3-002,3-003,3-004,3-005,3-007,6-003,6-005.

Test Example 11 Control effect test against sweet potato root-knot nematode 1 ml of test chemical solution B of the compound of the present invention was treated to a cell stock planted seedling seedling (about 2 weeks after germination) filled with 10 g of soil per cell. did. One hour after the treatment, water containing 2 L larvae of Meloidogyne incognita (2 L larvae: 100/1 ml) was inoculated to the strain, 1 ml per cell. It was kept in a greenhouse for 3 weeks, and the degree of root nodules formed at the root was determined according to the following disease index and disease severity, and the efficiency (%) for the untreated area was calculated by the following equation.

  <Disease index> 0: No humps are observed. 1: A hump is recognized by a part of root system.

              2: A hump is recognized in the whole root system. 3: A large hump is recognized.

              4: A large hump is recognized in the whole root system.

[Disease severity] = [Σ (attack index × number of diseased strains by index) / (4 × number of strains)] × 100
Efficacy (%) = [1- (treatment area incidence / no treatment area incidence)] × 100
As a result, among the tested compounds, the following compounds showed an efficiency (%) of 50% or more.
The present compound: No. 1-003, 1-005, 3-003, 7-002.

Test Example 12 Insecticidal test against southern nematode nematode Sterile water (larvae 10) containing 2 L larvae of calli-cultivated nematode nematode (Pratylenchus coffeae) after dispensing 60 μl of potato dextrose 1% agar medium to a 96-well plate 30 μl per well was added. From this, 10 μl of test drug solution B of the compound of the present invention was added to each well and allowed to stand at 25 ° C. under dark conditions. The number of inactive larvae 4 days after the addition of the drug was counted, and the efficiency (%) relative to the untreated group was calculated by the following equation.

efficacy (%) = (number of inactive larvae in treated area / number of active larvae in untreated area) x 100
As a result, among the tested compounds, the following compounds showed an efficiency (%) of 50% or more.
The present compound: No. 1-003.

Test Example 13 Insecticidal test for torsion stomachworms After dispensing 60 μl of potato dextrose 1% agar medium to a 96-well plate, sterile water (10 eggs / 3 μl) containing eggs of torsion stomachworms (Haemonchus contortus), 30 μl was added per well. From this, 10 μl of test drug solution B of the compound of the present invention was added to each well and allowed to stand at 25 ° C. under dark conditions. The number of unhatched eggs and the number of inactive larvae 4 days after the addition of the drug were measured, and the efficiency (%) for the untreated group was calculated from the same calculation formula as in Test Example 9.

As a result, among the tested compounds, the following compounds showed an efficiency (%) of 50% or more.
Compound of the present invention: No.1-001,1-002,1-003,1-004,1-005,1-006,1-007,2-001,3-002,3-003,3-005, 6-003.

  The N-alkenyl-substituted amide compound according to the present invention exhibits excellent pest control activity, particularly bactericidal / nematicidal activity, and has almost no adverse effects on non-target organisms such as mammals, fish and useful insects. There is no very useful compound.

Claims (13)

Formula (I):

Wherein, G ¹ represents a structure represented by G ¹ -1~G ¹ -51,


W represents an oxygen atom or a sulfur atom,
X ¹ represents a halogen atom, nitro, C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl,
X ² represents a hydrogen atom or a halogen atom,
X ³ represents a hydrogen atom or C ₁ -C ₄ alkyl,
Y ¹ represents a halogen atom, cyano, nitro, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy or C ₁ -C ₄ alkylthio,
Y ² is hydrogen atom, halogen atom, cyano, methyl, trifluoromethyl, C ₁ -C ₄ alkoxymethyl, C ₁ -C ₄ alkylthiomethyl, C ₁ -C ₄ alkylsulfinylmethyl, C ₁ -C ₄ alkylsulfonyl represents methyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy or _C 1 -C ₄ alkylthio,
Y ³ represents a hydrogen atom, a halogen atom, cyano, nitro, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₂ -C ₄ alkenyl, C ₂ -C ₄ haloalkenyl, -OR ⁷ , -S ( ^{_{O) r R 7, -C (}} R 8) = NOR 9, -C (O) NH 2, -C (S) NH 2, D-3, D-7, D-11, D-22, D- Represents 28 or D-29,
Y ⁴ represents a hydrogen atom, a halogen atom, cyano or methyl,
D-3, D-7, D-11, D-22, D-28 and D-29 each represent an aromatic heterocycle represented by the following structural formula;

Z is a halogen atom, cyano, nitro, C ₁ -C ₄ alkyl, trifluoromethyl, methoxy, difluoromethoxy, trifluoromethoxy, methylthio, methylsulfinyl, methylsulfonyl, trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethyl When sulfonyl or phenyl is represented and m or n represents 2 or more, each Z may be the same as or different from each other. Furthermore, when two Zs are adjacent, they are adjacent. The two Z's may form a 6-membered ring with the carbon atom to which each Z binds by forming -CH = CH-CH = CH-
R ¹ and R ² are each independently a hydrogen atom, a halogen atom, nitro, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₃ -C ₆ cycloalkyl (C ₁ -C ₄ ) alkyl, C ₁ -C ₄ alkoxy _(C 1 ~C ₄₎ represents alkyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₄ alkoxy or _C 1 -C ₄ haloalkoxy,
R ³ and R ⁴ are each independently a hydrogen atom, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxymethyl, C ₁ -C ₄ alkylthiomethyl, C ₁ -C ₄ alkyl sulfinyl methyl or C ₁ -C ₄ alkylsulfonyl or represents methyl,
Alternatively, R ³ and R ⁴ together form an ethylene chain to form a cyclopropyl ring with the carbon atom to which R ³ and R ⁴ are bonded,
R ⁵ is a hydrogen atom, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, (C ₁ -C ₂ ) alkyl substituted by R ¹⁰ , C ₃ -C ₆ cycloalkyl, C ₂ -C ₄ alkenyl. , C ₃ -C ₄ alkynyl, -OH, C ₁ ~C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ haloalkylthio, -C a ^{(O) R 11} or _C 1 -C ₄ alkoxycarbonyl Represent,
R ⁶ represents C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl,
R ⁷ is C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy (C ₁ -C ₂ ) alkyl, E-5, E-14, C ₃ -C ₄ alkenyl, C ₃ -C ₄ represents haloalkenyl, C ₃ -C ₄ alkynyl, C ₃ -C ₄ haloalkynyl, phenyl substituted by phenyl or _{(Z) m,}
E-5 and E-14 each represent a saturated heterocyclic ring represented by the following structural formula,

R ⁸ represents a hydrogen atom or C ₁ -C ₄ alkyl,
R ⁹ represents C ₁ -C ₄ alkyl,
R ¹⁰ represents cyano, —OR ¹³ , C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkoxycarbonyl, —C (O) NH ₂ or —C (S) NH ₂ ,
R ¹¹ represents C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxymethyl, C ₃ -C ₄ cycloalkyl or C ₂ -C ₄ alkenyl,
R ¹² represents C ₁ -C ₄ alkyl, and when p represents 2, each R ¹² may be the same as or different from each other;
R ¹³ represents C ₁ -C ₄ alkyl, C ₂ -C ₄ haloalkyl, C ₁ -C ₄ alkylcarbonyl, C ₃ -C ₆ cycloalkylcarbonyl or C ₁ -C ₄ alkoxycarbonyl,
m represents 1, 2, 3, 4 or 5;
n represents 0, 1, 2, 3 or 4;
p represents 0, 1 or 2;
r represents 0, 1 or 2. ]
Or an N-oxide or a salt thereof. G ^{1 is, G 1 -1, G 1 -2} , G 1 -3, G 1 -7, G 1 -8, G 1 -9, G 1 -11, G 1 -12, G 1 -13, G ¹ -16, G ¹ -27, G ¹ -32, G ¹ -33, G ¹ -44 or G ¹ -50
W represents an oxygen atom,
X ¹ represents a halogen atom, nitro, methyl, ethyl or C ₁ -C ₂ haloalkyl,
X ² represents a hydrogen atom, a fluorine atom or a chlorine atom,
X ³ represents a hydrogen atom, methyl or ethyl,
Y ¹ represents a halogen atom or methyl;
Y ² represents a hydrogen atom, a halogen atom, C ₁ -C ₃ alkoxy or methylthio,
Y ³ represents a halogen atom, trifluoromethyl, —OR ⁷ , —C (R ⁸ ) ═NOR ⁹ or D-7,
Y ⁴ represents a hydrogen atom or a halogen atom,
Z represents a halogen atom or trifluoromethyl,
R ¹ and R ² each independently represent a hydrogen atom, a halogen atom, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl or C ₁ -C ₄ alkoxy;
R ³ represents a hydrogen atom or methyl,
R ⁴ represents a hydrogen atom,
R ⁵ represents a hydrogen atom, cyclopropyl or methoxy,
R ⁶ represents methyl,
R ⁷ represents C ₁ -C ₄ haloalkyl,
R ⁸ represents a hydrogen atom or methyl,
R ⁹ represents methyl or ethyl,
n represents 0 or 1,
r represents 0,
The N-alkenyl substituted amide compound or a salt thereof according to claim 1. G ¹ represents a structure represented by G ¹ -1, G ¹ -2, G ¹ -3, G ¹ -7, G ¹ -11, G ¹ -27 or G ¹ -33;
X ¹ represents a halogen atom, methyl, difluoromethyl or trifluoromethyl,
X ² represents a hydrogen atom,
X ³ represents methyl,
Y ¹ represents a halogen atom,
Y ² represents a hydrogen atom,
Y ³ represents a halogen atom or trifluoromethyl,
Y ⁴ represents a hydrogen atom,
R ¹ and R ² each independently represents a hydrogen atom, a halogen atom, methyl or methoxy,
R ³ represents a hydrogen atom,
R ⁵ represents a hydrogen atom,
The N-alkenyl substituted amide compound according to claim 2. Formula (IIa):

[Wherein Y ¹ represents a halogen atom,
Y ² represents a hydrogen atom,
Y ³ represents a halogen atom or trifluoromethyl,
Y ⁴ represents a hydrogen atom,
R ¹ and R ² each independently represents a hydrogen atom, a halogen atom, methyl or methoxy,
R ³ represents a hydrogen atom,
R ⁴ represents a hydrogen atom. ]
The manufacturing intermediate of the N-alkenyl substituted amide compound of Claims 1-3 represented by these.   A pest control composition containing one or more selected from the N-alkenyl-substituted amide compounds according to claim 1 as an active ingredient.   An agricultural or horticultural fungicide or nematicide composition containing one or more selected from the N-alkenyl-substituted amide compounds according to claim 1 as an active ingredient.   The agricultural or horticultural fungicide or nematicide composition according to claim 6 for spraying foliage on plants.   The agricultural or horticultural fungicide or nematicide composition according to claim 6 for treating soil on which plants grow.   The agricultural or horticultural fungicide or nematicide composition according to claim 6 for treating plant seeds, tuberous roots and rhizomes.   A mammal or avian antifungal agent or parasite control agent composition comprising, as an active ingredient, one or more selected from the N-alkenyl-substituted amide compounds according to claim 1.   The endoparasite control composition according to claim 10 for oral administration to mammals or birds.   The endoparasite control agent composition according to claim 10 for parenteral administration to mammals or birds.   The endoparasite control composition according to claim 12, wherein the method of parenteral administration to mammals or birds is transdermal administration.