JP2019151593A - Phenyl acetylene-substituted amide compound and pest control agent - Google Patents

Abstract

To provide a pest control agent, particularly a bactericide and a nematicide.SOLUTION: The present invention provides a phenyl acetylene-substituted amide compound represented by formula (I), an N-oxide or a salt thereof, and a pest control agent containing the same. [Gis a structure represented by G-1, G-3 or the like, Gis a structure represented by G-1, G-4 or the like, A is a nitrogen atom or C-Y, Xis a halogen atom, trifluoromethyl or the like, Xis a hydrogen atom, a fluorine atom or the like, Yis a hydrogen atom, a halogen atom or the like, Yand Yindependently represent a halogen atom or the like, Rand Rindependently represent a hydrogen atom, a fluorine atom, methyl, methoxy or the like, Ris a hydrogen atom, methyl or the like, Ris a hydrogen atom or the like, Ris a hydrogen atom or the like, Z is a halogen atom, C-Cis haloalkyl or the like, n is 0, 1, 2, 3 or 4, m is 0, 1, 2, 3, 4].SELECTED DRAWING: None

Description

  The present invention relates to a novel phenylacetylene-substituted amide compound, its N-oxide, or a salt thereof, and a pest control agent containing these compounds as active ingredients.

  Conventionally, regarding phenylacetylene-substituted amide compounds, for example, N- [1- [4- [4- (pyrimidin-5-yloxy) phenyl] ethynyl] phenyl] propan-2-yl] cyclopropanecarboxamide, N- [1 -[4-[[4- (Pyridin-4-yloxy) phenyl] ethynyl] phenyl] propan-2-yl] acetamide, N- [1- [4-[[4- (pyrimidin-5-yloxy)] phenyl ] Ethynyl] phenyl] propan-2-yl] acetamide, N- [1- [4-[(4-phenoxyphenyl) ethynyl] phenyl] propan-2-yl] acetamide and the like have acetyl CoA carboxylase inhibitory activity. It is known (see Patent Document 1).

  In addition, regarding phenylacetylene-substituted amide compounds, N- [2- [3-chloro-5-[(2-fluorophenyl) ethynyl] pyridin-2-yl] -2,2-difluoroethyl] -3- (difluoro Methyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide (see Patent Document 2), N- [2- [3-chloro-5- (phenylethynyl) pyridin-2-yl] -2 , 2-Difluoroethyl] -2- (trifluoromethyl) benzamide (see Patent Document 3), N- [2- [3-chloro-5-[(4-fluorophenyl) ethynyl] pyridin-2-yl] -2- [Isopropoxyimino] ethyl] -2- (trifluoromethyl) benzamide (see Patent Document 4), N- [1- [3-chloro-5- (phenylethynyl)] Lysin-2-yl] propan-2-yl] -3- (difluoromethyl) -1-methyl-1-H-pyrazolecarboxamide (see Patent Document 5) and 3-methyl-N- [2-methyl It is known that -1- [2-methyl-4- (phenylethynyl) phenyl] -1-oxopropanon-2-yl] thiophenecarboxamide (see Patent Document 6) exhibits bactericidal activity and nematicidal activity. ing.

  However, there is no disclosure regarding the phenylacetylene-substituted amide compounds according to the present invention, and their usefulness as pest control agents is not known.

International Publication No. 2012/028676 JP 2017-39722 A JP 2017-36275 A Japanese Patent Application Laid-Open No. 2016-11286 International Publication No. 2015/125824 International Publication No. 2006/016708

  Infections and infestations of pests such as pathogens and parasites can occur when the host is a plant such as a shellfish, fruit tree, vegetable, or ornamental plant. This causes serious economic losses not only to Shoko, producers, but also to consumers. Therefore, effective control of these pests is an extremely important issue in order to achieve efficient and stable production of crops. In addition, when the host is a companion animal, pet animal, livestock, poultry animal, 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 a challenge 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 of the 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 also becoming apparent. Under such circumstances, development of novel pesticides and effective control methods that have not only excellent control activity against pathogenic bacteria and parasites but also advanced control characteristics such as low toxicity and low persistence is always expected. Has been.

  As a result of intensive research aimed at solving the above problems, the present inventors have found that the novel phenylacetylene-substituted amide compound represented by the following (I) has excellent pest control activity, particularly antifungal and nematode activity And has been found to be a very useful compound having almost no adverse effects on non-target organisms such as plants, mammals, fish, useful insects and natural enemies.

  That is, the present invention relates to [1] to [13].

[1]
Formula (I):

[In the formula, G ¹ represents a structure represented by G ¹ -1 to G ¹ -13;

G ² is represents a structure represented by G ² -1~G ² -4

A represents a nitrogen atom or CY ^A ,
X ¹ is a halogen atom, nitro, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ haloalkylthio, represents C ₁ -C ₄ haloalkylsulfinyl or C ₁ -C ₄ haloalkylsulfonyl,
X ² represents a hydrogen atom, a halogen atom or C ₁ -C ₄ alkyl,
X ³ represents a hydrogen atom or C ₁ -C ₄ alkyl,
Y ^A represents a hydrogen atom, a halogen atom or methyl,
Y ¹ represents a hydrogen atom, a halogen atom, C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl.
Y ² represents a halogen atom, cyano, nitro, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy or C ₁ -C ₆ haloalkoxy, and when m represents 2 or more Represents that each Y ² may be the same as or different from each other;
R ¹ and R ² are each independently a hydrogen atom, a halogen atom, cyano, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy or C ₁ -C ₄ alkoxy or a carbonyl, or by R ¹ and R ² form a C ₂ -C ₅ alkylene chain together, 3-6 membered ring together with the carbon to which R ¹ and R ² are bonded Represents the formation of
R ³ and R ⁴ each independently represent a hydrogen atom or C ₁ -C ₆ alkyl,
Alternatively, R ³ and R ⁴ together form an ethylene chain, thereby forming 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 ₆ alkyl, C ₁ -C ₆ haloalkyl, (C ₁ -C ₂ ) alkyl substituted by R ⁶ , C ₃ -C ₆ cycloalkyl, C ₂ -C ₆ alkenyl , C ₃ -C ₆ alkynyl, -OH, C ₁ ~C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ haloalkylthio, -C a (O) R ⁷ or C ₁ -C ₄ alkoxycarbonyl Represent,
R ⁶ represents cyano, C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkoxycarbonyl, -C (O) NH ₂ or -C (S) NH ₂
R ⁷ represents C ₁ -C ₄ alkyl or C ₁ -C ₄ alkoxymethyl,
Z is 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, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ represents alkylsulfonyl, C ₁ -C ₄ haloalkylthio, a C ₁ -C ₄ haloalkylsulfinyl or C ₁ -C ₄ haloalkylsulfonyl, when n is 2 or more, each of Z may be the same or different from each other, and when two Zs are adjacent, the two adjacent Zs together form -CH = CH-CH = CH- Thus, a hydrogen atom on —CH═CH—CH═CH— formed by two Z's may form a 6-membered ring with the carbon atom to which each Z is bonded, and may be replaced by R ⁸ . Represents
R ⁸ represents a halogen atom, C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl.
n represents an integer of 0, 1, 2, 3 or 4;
r represents an integer of 0, 1 or 2;
m represents an integer of 0, 1, 2, 3 or 4. ]
Or a N-oxide or a salt thereof.

[2]
G ^{1 is, G 1 -1~G 1 -4, G} 1 -7, G 1 -8, represents G ¹ -10 or G ¹ -11,
G ² represents G ² -1 or G ² -4,
X ¹ represents a halogen atom or C ₁ -C ₄ haloalkyl,
X ² represents a hydrogen atom or a halogen atom,
X ³ represents methyl
Y ^A represents a hydrogen atom,
Y ¹ represents a halogen atom,
Y ² represents a halogen atom,
R ¹ and R ² each independently represent a hydrogen atom, a halogen atom, C ₁ -C ₆ alkyl or C ₁ -C ₆ alkoxy, or R ¹ and R ² together form an ethylene chain. Represents forming a cyclopropyl ring together with the carbon atom to which R ¹ and R ² are bonded,
R ³ and R ⁴ each independently represent a hydrogen atom or methyl, or R ³ and R ⁴ together form an ethylene chain, whereby a carbon atom to which R ³ and R ⁴ are bonded. Together with a cyclopropyl ring,
R ⁵ represents a hydrogen atom,
Z represents a halogen atom or a C ₁ -C ₄ haloalkyl, when n is 2, each Z is independently selected from groups or phases the same as each other, further, two Z are adjacent In some cases, two adjacent Z together form -CH = CH-CH = CH- to form a 6-membered ring with the carbon atom to which each Z is attached, and the two Z Represents that the hydrogen atom on —CH═CH—CH═CH— formed by may be substituted by R ⁸ ;
R ⁸ represents a halogen atom,
n represents an integer of 1 or 2,
m represents an integer of 0 or 1.
[1] The phenylacetylene-substituted amide compound according to [1], an N-oxide thereof or a salt thereof.

[3]
Formula (II):

Wherein, G ² represents a G ² -1 or G ² -4,

A represents a nitrogen atom or CY ^A ,
Y ^A represents a hydrogen atom,
Y ¹ represents a halogen atom,
Y ² represents a halogen atom,
R ¹ and R ² each independently represent a hydrogen atom, fluorine, methyl or methoxy,
Alternatively, R ¹ and R ² together form an ethylene chain, thereby forming a cyclopropyl ring with the carbon atom to which R ¹ and R ² are bonded,
R ³ and R ⁴ each independently represents a hydrogen atom or methyl,
R ⁵ represents a hydrogen atom,
Z represents a halogen atom or a C ₁ -C ₄ haloalkyl, when n is 2, each Z is independently selected from groups or phases the same as each other, further, two Z are adjacent In some cases, two adjacent Z together form -CH = CH-CH = CH- to form a 6-membered ring with the carbon atom to which each Z is attached, and the two Z Represents that the hydrogen atom on —CH═CH—CH═CH— formed by may be substituted by R ⁸ ;
R ⁸ represents a halogen atom,
n represents an integer of 0, 1 or 2
m represents an integer of 0 or 1. ]
A production intermediate of the phenylacetylene-substituted amide compound, its N-oxide or a salt thereof according to any one of [1] to [2].

[4]
A pest control composition comprising, as an active ingredient, at least one selected from the phenylacetylene-substituted amide compounds according to [1] to [2], N-oxides or salts thereof.
[5]
The antifungal agent or parasite control agent composition for mammals or birds, comprising as an active ingredient at least one selected from the phenylacetylene-substituted amide compounds according to [1] to [2], N-oxides or salts thereof .

[6]
The antifungal agent or parasite control agent composition according to [5] for oral administration to mammals or birds.

[7]
The antifungal or parasite control composition according to [5] for parenteral administration to mammals or birds.

[8]
The antifungal agent or parasite control agent composition according to [7], wherein the method of parenteral administration to mammals or birds is administration by injection.

[9]
The antifungal agent or parasite control agent composition according to [7], wherein the method of parenteral administration to mammals or birds is transdermal administration.

[10]
An agricultural and horticultural fungicide or nematicide composition containing, as an active ingredient, one or more selected from the phenylacetylene-substituted amide compounds according to [1] to [2], N-oxides or salts thereof.

[11]
The agricultural or horticultural fungicide or nematicide composition according to [10] for spraying foliage on plants.

[12]
The agricultural and horticultural fungicide or nematicide composition according to [10] for treating soil on which plants grow.

[13]
The agricultural and horticultural fungicide or nematicide composition according to [10] for treating plant seeds, tuberous roots and rhizomes.

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 satellite, 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 little adverse effect on target organisms such as plants, mammals, fish, useful insects, and infusions, and has low persistence and a low environmental burden.
Therefore, the present invention can provide a useful novel pest control agent.

  In the phenylacetylene-substituted amide compound represented by the formula (I) included in the present invention, an optically active substance resulting from the presence of one or more asymmetric carbon atoms may be present depending on the substituent. However, the present invention includes all optically active substances or racemates.

  As a halogen atom in this specification, a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom is mentioned. In addition, the notation of “halo” in this specification also represents these halogen atoms.

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

The expression “C _a -C _b alkyl” in the present specification represents a linear or branched hydrocarbon having a carbon number of _a to _b , such as methyl, ethyl, n-propyl, i- Specific examples include propyl, n-butyl, i-butyl, sec-butyl, tert-butyl, pentyl, 1-ethylpropyl, 2,2-dimethylpropyl, hexyl, etc., each having a specified number of carbon atoms Selected.

In the present specification, the expression “C _a -C _b haloalkyl” 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. 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, chloromethyl, bromomethyl, iodomethyl, difluoromethyl, dichloromethyl, trifluoromethyl, chlorodifluoromethyl, trichloromethyl, bromodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2,2-trichloroethyl, 2-bromo-2,2-difluoroethyl, 1, 1,2,2-tetrafluoroethyl, 2-chloro-1,1,2-trifluoroethyl, pentafluoroethyl, 2,2-difluoropropyl, 3,3,3-trifluoropropyl, 3-bromo-3 , 3-Difluoropropyl, 2,2,3,3-tetrafluoropropyl, 2,2,3,3,3-pentafluoropropyl, 1,1,2,3,3,3 -Hexafluoropropyl, heptafluoropropyl, 1-fluoro-1- (methyl) ethyl, 1-chloro-1- (methyl) ethyl, 2,2,2-trifluoro-1- (methyl) ethyl, 2,2 , 2-Trifluoro-1- (trifluoromethyl) ethyl, 1,2,2,2-tetrafluoro-1- (trifluoromethyl) ethyl, 2,2,3,4,4,4-hexafluorobutyl Specific examples include 2,2,3,3,4,4,4-heptafluorobutyl, nonafluorobutyl 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 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, for example, cyclopropyl, cyclobutyl, 1-methylcyclopropyl, 2-methylcyclopropyl, cyclopentyl, 2,2-dimethylcyclopropyl, 1-methylcyclobutyl, cyclohexyl and the like. The range is selected.

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, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 2- Specific examples include methyl-2-propenyl, 3-methyl-3-butenyl and the like, each selected within the specified number of carbon atoms.

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, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 1-hexynyl Specific examples include 3-hexynyl, 3-methyl-1-pentynyl, 4-methyl-1-pentynyl, 3,3-dimethyl-1-butynyl, etc., each selected within the specified number of carbon atoms. The

In the present specification, the expression “C _a -C _b alkoxy” represents an alkyl-O— group having the previous meaning consisting of _a to _b carbon atoms, such as methoxy, ethoxy, n-propyloxy, i Specific examples include -propyloxy, n-butyloxy, i-butyloxy, sec-butyloxy, tert-butyloxy, pentyloxy, hexyloxy, and the like, and each is selected within the range of the designated number of carbon atoms.

In this 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 difluoromethoxy, trifluoromethoxy, chlorodifluoro. Methoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2-chloro-1,1,2-trifluoro Specific examples include ethoxy, 3,3,3-trifluoropropyloxy, 1,1,2,3,3,3-hexafluoropropyloxy, etc., each selected within the range of the specified 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, ethylthio, n-propylthio, i- Specific examples include propylthio, n-butylthio, i-butylthio, sec-butylthio, tert-butylthio and the like, each selected within the range of the specified 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, ethylsulfinyl, Specific examples include n-propylsulfinyl, i-propylsulfinyl and the like, each selected within the specified number of carbon atoms.

The expression “C _a -C _b alkylsulfonyl” in the present specification represents an alkyl-SO ₂ -group having the above-mentioned meaning consisting of _a to _b carbon atoms, for example, methylsulfonyl, ethylsulfonyl, n- Specific examples include propylsulfonyl, i-propylsulfonyl, and the like, each selected within the range of the specified 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 difluoromethylthio, trifluoromethylthio, chlorodifluoro. Methylthio, trichloromethylthio, bromodifluoromethylthio, 2,2,2-trifluoroethylthio, 1,1,2,2-tetrafluoroethylthio, 2-chloro-1,1,2-trifluoroethylthio, pentafluoro Ethylthio, 1,1,2,3,3,3-hexafluoropropylthio, heptafluoropropylthio, 1,2,2,2-tetrafluoro-1- (trifluoromethyl) ethylthio, nonafluorobutylthio, etc. Are given as specific examples and are selected within the range of each designated number of carbon atoms.

In the present specification, the expression “C _a -C _b haloalkylsulfinyl” represents a haloalkyl-S (O) — group having the above-mentioned meanings consisting of _a to _b carbon atoms, such as difluoromethylsulfinyl, trifluoro Specific examples include methylsulfinyl and the like, each selected within the range of the designated number of carbon atoms.

In the present specification, the expression “C _a -C _b haloalkylsulfonyl” represents a haloalkyl-SO ₂ -group having the above-mentioned meaning consisting of _a to _b carbon atoms, such as difluoromethylsulfonyl, trifluoromethylsulfonyl. Etc. are given as specific examples, and each is selected within the range of the designated 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, such as methoxycarbonyl, ethoxycarbonyl, Specific examples include n-propyloxycarbonyl, i-propyloxycarbonyl, n-butoxycarbonyl, i-butoxycarbonyl, tert-butoxycarbonyl and the like, each selected within the range of the designated number of carbon atoms.

In the present specification, the notation “(C _a -C _b ) alkyl substituted by R ⁶ ” indicates that the number of carbon atoms in which a hydrogen atom bonded to a carbon atom is arbitrarily substituted by any R ⁶ is _a to _b Represents an alkyl group having the above-mentioned meaning, and is selected in the range of the designated number of carbon atoms. At this time, when there are two or more substituents R ⁶ on each (C _a -C _b ) alkyl group, each R ⁶ may be the same as or different from each other.

In the present specification, the expression “C _a -C _b alkoxymethyl” represents a methyl group substituted by any C _a -C _b alkoxy group having the above-mentioned meaning, for example, methoxymethyl, ethoxymethyl and the like are specific examples. Each selected within a range of each specified number of carbon atoms.

In the present specification, “R ¹ and R ² together form a C ₂ -C ₅ alkylene chain, thereby forming a 3- to 6-membered ring with the carbon atom to which R ¹ and R ² are bonded. , R ¹ and R ² may form a 3- to 6-membered ring together with the carbon to which R ¹ and R ² are bonded, and specific examples of the notation include, for example, rings such as cyclopropane, cyclobutane, cyclopentane, and cyclohexane. , Selected for each specified number of 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 -I [wherein X ¹ represents a halogen atom, nitro, methyl or trifluoromethyl, and X ² represents a hydrogen atom. ].

G ¹ -II: G ¹ -I [where X ¹ and X ² represent a fluorine atom. ].

G ¹ -III: G ¹ -2 or G ¹ -3 [wherein X ¹ represents a halogen atom, difluoromethyl, trifluoromethyl or methanesulfonyl. ].

G ¹ -IV: G ¹ -4 [where X ¹ represents trifluoromethyl. ].

G ¹ -V: G ¹ -7 or G ¹ -8 [wherein X ¹ represents a halogen atom, methyl or trifluoromethyl. ].

G ¹ -VI: G ¹ -9 [wherein X ¹ represents trifluoromethyl and X ³ represents methyl. ].

G ¹ -VII: G ¹ -10 [wherein X ¹ represents difluoromethyl or trifluoromethyl, X ² represents a hydrogen atom, and X ³ represents methyl. ].

G ¹ -VIII: G ¹ -11 [wherein X ¹ represents difluoromethyl or trifluoromethyl, and X ³ represents methyl. ].

G ¹ -IX: G ¹ -13 [where X ¹ represents trifluoromethyl and r represents 0. ].

G ¹ -X: G1-1 [where X ¹ represents a chlorine atom, and X ² represents a fluorine atom or a chlorine atom.
].

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

G ¹ -XII: G ¹ -4 [where X ¹ represents a halogen atom, methyl or difluoromethyl.
].

G ¹ -XIII: G ¹ -5 or G ¹ -6 [where X ¹ represents difluoromethyl or trifluoromethyl. ].

G ¹ -XIV: G ¹ -7 or G ¹ -8 [wherein X ¹ represents difluoromethyl. ].

G ¹ -XV: G ¹ -9 [wherein X ¹ represents difluoromethyl and X ³ represents methyl. ].

G ¹ -XVI: G ¹ -10 [wherein X ¹ represents methyl, ethyl or trifluoromethyl, X ² represents a fluorine atom or a chlorine atom, and X ³ represents methyl. ].

G ¹ -XVII: G ¹ -12 [where X ¹ represents difluoromethyl or trifluoromethyl, and X ³ represents methyl. ].

G ¹ -XVIII: G ¹ -13 [where X ¹ represents methyl or trifluoromethyl, r is 0, 1
Or 2 is represented. ].

Of these, ^{G 1} -I~G ¹ -IX as range of the substituent of ^{G 1, G 1 -XIII, G} 1 -XV
, G ¹ -XVII or G ¹ -XVIII is more preferable, and G ¹ -I to G ¹ -IX are particularly preferable.

In the compounds included in the present invention, examples of the preferred range of substituents represented by A, Y ¹ and Y ² include the following groups Y-1 to YV.

That is, YI: A is a nitrogen atom, Y ¹ is a halogen atom, and Y ² is a hydrogen atom.

Y-II: A is a nitrogen atom, Y ¹ is a halogen atom, and Y ² is a halogen atom.

Y-III: A is a nitrogen atom, Y ¹ is methyl, and Y ² is a hydrogen atom.

Y-IV: A is CY ¹ , Y ¹ is a halogen atom, and Y ² is a hydrogen atom.

YV: A is CY ¹ , Y ¹ is a halogen atom, and Y ² is a halogen atom.

Among these, the combination of substituents represented by A, Y ¹ and Y ² is preferably Y-1, Y-II or Y-IV, more preferably YI or Y-IV.

Examples of combinations of preferred ranges of the substituents represented by R ¹ , R ² , R ³ and R ⁴ in the compounds included in the present invention include the following groups of RI to R-VI.

That is, RI: R ¹ and R ² are hydrogen atoms, R ³ is a hydrogen atom or methyl, and R ⁴ is a hydrogen atom.

R-II: R ¹ and R ² are fluorine atoms, R ³ is a hydrogen atom or methyl, and R ⁴ is a hydrogen atom.

R-III: R ¹ is C ₁ -C ₆ alkoxy, R ² and R ⁴ are hydrogen atoms, and R ³ is methyl.

R-IV: R ¹ and R ² are combined to form an ethylene chain, thereby forming a cyclopropyl ring with the carbon atom to which R ¹ and R ² are bonded, and R ³ and R ⁴ are hydrogen atoms.

RV: R ³ and R ⁴ together form an ethylene chain to form a cyclopropyl ring with the carbon atom to which R ² and R 3 are bonded, and R ¹ and R ² are hydrogen atoms.

R-VI: R ¹ and R ² are methyl, and R ³ and R ⁴ are hydrogen atoms at the same time.

Of these, the combination of substituents represented by R ¹ , R ² , R ³ or R ⁴ is preferably RI to R-IV, more preferably R-II or R-III.

In the compounds included in the present invention, a preferred range of the substituent of R ^5, include the following groups R ⁵ -I~R ⁵ -IV.

That is, R ⁵ -I: a hydrogen atom.

R ⁵ -II: cyclopropyl.

R ⁵ -III: C ₁ -C ₄ alkoxycarbonyl.

R ⁵ -IV: C ₁ -C ₆ alkyl.

Among them, as the range of the substituent of R ^5, R ⁵ -I or R ⁵ -II are preferred, R ⁵ -I is particularly preferred.

Preferred ranges of the substituent represented by G ² encompassed by the present invention, include the following groups G ² -I~G ² -IX.

That is, G ² -I: G ² -1 [where n represents 1 and Z represents a halogen atom. ].

G ² -II: G ² -1 [where n represents 1 and Z represents trifluoromethyl. ]
G ² -III: G ² -1 [wherein n represents 2 and Z represents a halogen atom. ]
G ² -IV: G ² -1 [wherein n represents 2 and Z represents a halogen atom or trifluoromethyl. ].

G ² -V: G ² -3 [where n represents 1 and Z represents a halogen atom. ].

G ² -VI: G ² -3 [where n represents 2 and Z forms —CH═CH—CH═CH— to form a 6-membered ring with the carbon atom to which each Z is bonded. Represents what to do. ].

G ² -VII: G ² -4 [wherein n represents 1 and Z represents a halogen atom. ].

G ² -VIII: G ² -4 [where n represents 2 and Z forms —CH═CH—CH═CH— to form a 6-membered ring with the carbon atom to which each Z is bonded. Represents what to do. ].

G ² -IX: G ² -4 [where n represents 2 and Z forms —CH═CH—CH═CH— to form a 6-membered ring with the carbon atom to which each Z is bonded. indicates that, and the hydrogen atom of the above -CH = CH-CH = CH-, which is formed by the two Z represents that may be substituted by R ^8, R ⁸ represents a halogen atom. ].

Among them, as the range of the substituent of G ^2, preferably G ² -I~G ² -IV or G ² -IX, further, G ² -II~G ² -IV is particularly preferred.

Each group which shows the preferable range of each substituent in these compounds included in the present invention can be arbitrarily combined, and the preferable ranges of the compounds of the present invention are shown in Table 1, respectively.
Table 1 ――――――――――――――――――――――――――――――――――――――
G ¹ A, Y ^{1 to} Y ⁸ R ¹ -R ⁴ G ² G ¹ A, Y ^{1 to} Y ⁸ R ¹ -R ⁴ G ²
――――――――――――――――――――――――――――――――――――――
G ¹ -I YI RI G ² -IG ¹ -I YI RI G ² -II
G ¹ -I YI RI G ² -III G ¹ -I YI RI G ² -IV
G ¹ -I YI RI G ² -VIII G ¹ -I YI RI G ² -IX
G ¹ -I Y-II RI G ² -IG ¹ -I Y-II RI G ² -II
G ¹ -I Y-II RI G ² -III G ¹ -I Y-II RI G ² -IV
G ¹ -I Y-II RI G ² -VIII G ¹ -I Y-II RI G ² -IX
G ¹ -I Y-IV RI G ² -IG ¹ -I Y-IV RI G ² -II
G ¹ -I Y-IV RI G ² -III G ¹ -I Y-IV RI G ² -IV
G ¹ -I Y-IV RI G ² -VIII G ¹ -I Y-IV RI G ² -IX
G ¹ -I YV RI G ² -IG ¹ -I YV RI G ² -II
G ¹ -I YV RI G ² -III G ¹ -I YV RI G ² -IV
G ¹ -I YV RI G ² -VIII G ¹ -I YV RI G ² -IX
G ¹ -I YI R-II G ² -IG ¹ -I YI R-II G ² -II
G ¹ -I YI R-II G ² -III G ¹ -I YI R-II G ² -IV
G ¹ -I YI R-II G ² -VIII G ¹ -I YI R-II G ² -IX
G ¹ -I Y-II R-II G ² -IG ¹ -I Y-II R-II G ² -II
G ¹ -I Y-II R-II G ² -III G ¹ -I Y-II R-II G ² -IV
G ¹ -I Y-II R-II G ² -VIII G ¹ -I Y-II R-II G ² -IX
G ¹ -I Y-IV R-II G ² -IG ¹ -I Y-IV R-II G ² -II
G ¹ -I Y-IV R-II G ² -III G ¹ -I Y-IV R-II G ² -IV
G ¹ -I Y-IV R-II G ² -VIII G ¹ -I Y-IV R-II G ² -IX
G ¹ -I YV R-II G ² -IG ¹ -I YV R-II G ² -II
G ¹ -I YV R-II G ² -III G ¹ -I YV R-II G ² -IV
G ¹ -I YV R-II G ² -VIII G ¹ -I YV R-II G ² -IX
G ¹ -I YI R-III G ² -IG ¹ -I YI R-III G ² -II
G ¹ -I YI R-III G ² -III G ¹ -I YI R-III G ² -IV
G ¹ -I YI R-III G ² -VIII G ¹ -I YI R-III G ² -IX
G ¹ -I Y-II R-III G ² -IG ¹ -I Y-II R-III G ² -II
G ¹ -I Y-II R-III G ² -III G ¹ -I Y-II R-III G ² -IV
G ¹ -I Y-II R-III G ² -VIII G ¹ -I Y-II R-III G ² -IX
G ¹ -I Y-IV R-III G ² -IG ¹ -I Y-IV R-III G ² -II
G ¹ -I Y-IV R-III G ² -III G ¹ -I Y-IV R-III G ² -IV
G ¹ -I Y-IV R-III G ² -VIII G ¹ -I Y-IV R-III G ² -IX
G ¹ -I YV R-III G ² -IG ¹ -I YV R-III G ² -II
G ¹ -I YV R-III G ² -III G ¹ -I YV R-III G ² -IV
G ¹ -I YV R-III G ² -VIII G ¹ -I YV R-III G ² -IX
G ¹ -I YI R-IV G ² -IG ¹ -I YI R-III G ² -II
G ¹ -I YI R-IV G ² -III G ¹ -I YI R-III G ² -IV
G ¹ -I YI R-IV G ² -VIII G ¹ -I YI R-III G ² -IX
G ¹ -I Y-II R-IV G ² -IG ¹ -I Y-II R-III G ² -II
G ¹ -I Y-II R-IV G ² -III G ¹ -I Y-II R-IV G ² -IV
G ¹ -I Y-II R-IV G ² -VIII G ¹ -I Y-II R-IV G ² -IX
G ¹ -I Y-IV R-IV G ² -IG ¹ -I Y-IV R-IV G ² -II
G ¹ -I Y-IV R-IV G ² -III G ¹ -I Y-IV R-IV G ² -IV
G ¹ -I Y-IV R-IV G ² -VIII G ¹ -I Y-IV R-IV G ² -IX
G ¹ -I YV R-IV G ² -IG ¹ -I YV R-IV G ² -II
G ¹ -I YV R-IV G ² -III G ¹ -I YV R-IV G ² -IV
G ¹ -I YV R-IV G ² -VIII G ¹ -I YV R-IV G ² -IX
G ¹ -II YI RI G ² -IG ¹ -II YI RI G ² -II
G ¹ -II YI RI G ² -III G ¹ -II YI RI G ² -IV
G ¹ -II YI RI G ² -VIII G ¹ -II YI RI G ² -IX
G ¹ -II Y-II RI G ² -IG ¹ -II Y-II RI G ² -II
G ¹ -II Y-II RI G ² -III G ¹ -II Y-II RI G ² -IV
G ¹ -II Y-II RI G ² -VIII G ¹ -II Y-II RI G ² -IX
G ¹ -II Y-IV RI G ² -IG ¹ -II Y-IV RI G ² -II
G ¹ -II Y-IV RI G ² -III G ¹ -II Y-IV RI G ² -IV
G ¹ -II Y-IV RI G ² -VIII G ¹ -II Y-IV RI G ² -IX
G ¹ -II YV RI G ² -IG ¹ -II YV RI G ² -II
G ¹ -II YV RI G ² -III G ¹ -II YV RI G ² -IV
G ¹ -II YV RI G ² -VIII G ¹ -II YV RI G ² -IX
G ¹ -II YI R-II G ² -IG ¹ -II YI R-II G ² -II
G ¹ -II YI R-II G ² -III G ¹ -II YI R-II G ² -IV
G ¹ -II YI R-II G ² -VIII G ¹ -II YI R-II G ² -IX
G ¹ -II Y-II R-II G ² -IG ¹ -II Y-II R-II G ² -II
G ¹ -II Y-II R-II G ² -III G ¹ -II Y-II R-II G ² -IV
G ¹ -II Y-II R-II G ² -VIII G ¹ -II Y-II R-II G ² -IX
G ¹ -II Y-IV R-II G ² -IG ¹ -II Y-IV R-II G ² -II
G ¹ -II Y-IV R-II G ² -III G ¹ -II Y-IV R-II G ² -IV
G ¹ -II Y-IV R-II G ² -VIII G ¹ -II Y-IV R-II G ² -IX
G ¹ -II YV R-II G ² -IG ¹ -II YV R-II G ² -II
G ¹ -II YV R-II G ² -III G ¹ -II YV R-II G ² -IV
G ¹ -II YV R-II G ² -VIII G ¹ -II YV R-II G ² -IX
G ¹ -II YI R-III G ² -IG ¹ -II YI R-III G ² -II
G ¹ -II YI R-III G ² -III G ¹ -II YI R-III G ² -IV
G ¹ -II YI R-III G ² -VIII G ¹ -II YI R-III G ² -IX
G ¹ -II Y-II R-III G ² -IG ¹ -II Y-II R-III G ² -II
G ¹ -II Y-II R-III G ² -III G ¹ -II Y-II R-III G ² -IV
G ¹ -II Y-II R-III G ² -VIII G ¹ -II Y-II R-III G ² -IX
G ¹ -II Y-IV R-III G ² -IG ¹ -II Y-IV R-III G ² -II
G ¹ -II Y-IV R-III G ² -III G ¹ -II Y-IV R-III G ² -IV
G ¹ -II Y-IV R-III G ² -VIII G ¹ -II Y-IV R-III G ² -IX
G ¹ -II YV R-III G ² -IG ¹ -II YV R-III G ² -II
G ¹ -II YV R-III G ² -III G ¹ -II YV R-III G ² -IV
G ¹ -II YV R-III G ² -VIII G ¹ -II YV R-III G ² -IX
G ¹ -II YI R-IV G ² -IG ¹ -II YI R-III G ² -II
G ¹ -II YI R-IV G ² -III G ¹ -II YI R-III G ² -IV
G ¹ -II YI R-IV G ² -VIII G ¹ -II YI R-III G ² -IX
G ¹ -II Y-II R-IV G ² -IG ¹ -II Y-II R-III G ² -II
G ¹ -II Y-II R-IV G ² -III G ¹ -II Y-II R-IV G ² -IV
G ¹ -II Y-II R-IV G ² -VIII G ¹ -II Y-II R-IV G ² -IX
G ¹ -II Y-IV R-IV G ² -IG ¹ -II Y-IV R-IV G ² -II
G ¹ -II Y-IV R-IV G ² -III G ¹ -II Y-IV R-IV G ² -IV
G ¹ -II Y-IV R-IV G ² -VIII G ¹ -II Y-IV R-IV G ² -IX
G ¹ -II YV R-IV G ² -IG ¹ -II YV R-IV G ² -II
G ¹ -II YV R-IV G ² -III G ¹ -II YV R-IV G ² -IV
G ¹ -II YV R-IV G ² -VIII G ¹ -II YV R-IV G ² -IX
G ¹ -III YI RI G ² -IG ¹ -III YI RI G ² -II
G ¹ -III YI RI G ² -III G ¹ -III YI RI G ² -IV
^{G 1 -III YI RI G 2 -VIII} G 1 -III YI RI G 2 -IX
G ¹ -III Y-II RI G ² -IG ¹ -III Y-II RI G ² -II
G ¹ -III Y-II RI G ² -III G ¹ -III Y-II RI G ² -IV
^{G 1 -III Y-II RI G} 2 -VIII G 1 -III Y-II RI G 2 -IX
G ¹ -III Y-IV RI G ² -IG ¹ -III Y-IV RI G ² -II
G ¹ -III Y-IV RI G ² -III G ¹ -III Y-IV RI G ² -IV
^{G 1 -III Y-IV RI G} 2 -VIII G 1 -III Y-IV RI G 2 -IX
G ¹ -III YV RI G ² -IG ¹ -III YV RI G ² -II
G ¹ -III YV RI G ² -III G ¹ -III YV RI G ² -IV
^{G 1 -III YV RI G 2 -VIII} G 1 -III YV RI G 2 -IX
G ¹ -III YI R-II G ² -IG ¹ -III YI R-II G ² -II
G ¹ -III YI R-II G ² -III G ¹ -III YI R-II G ² -IV
^{G 1 -III YI R-II G} 2 -VIII G 1 -III YI R-II G 2 -IX
G ¹ -III Y-II R-II G ² -IG ¹ -III Y-II R-II G ² -II
G ¹ -III Y-II R-II G ² -III G ¹ -III Y-II R-II G ² -IV
^{G 1 -III Y-II R-} II G 2 -VIII G 1 -III Y-II R-II G 2 -IX
G ¹ -III Y-IV R-II G ² -IG ¹ -III Y-IV R-II G ² -II
G ¹ -III Y-IV R-II G ² -III G ¹ -III Y-IV R-II G ² -IV
^{G 1 -III Y-IV R-} II G 2 -VIII G 1 -III Y-IV R-II G 2 -IX
G ¹ -III YV R-II G ² -IG ¹ -III YV R-II G ² -II
G ¹ -III YV R-II G ² -III G ¹ -III YV R-II G ² -IV
^{G 1 -III YV R-II G} 2 -VIII G 1 -III YV R-II G 2 -IX
G ¹ -III YI R-III G ² -IG ¹ -III YI R-III G ² -II
G ¹ -III YI R-III G ² -III G ¹ -III YI R-III G ² -IV
^{G 1 -III YI R-III G} 2 -VIII G 1 -III YI R-III G 2 -IX
G ¹ -III Y-II R-III G ² -IG ¹ -III Y-II R-III G ² -II
G ¹ -III Y-II R-III G ² -III G ¹ -III Y-II R-III G ² -IV
^{G 1 -III Y-II R-} III G 2 -VIII G 1 -III Y-II R-III G 2 -IX
G ¹ -III Y-IV R-III G ² -IG ¹ -III Y-IV R-III G ² -II
G ¹ -III Y-IV R-III G ² -III G ¹ -III Y-IV R-III G ² -IV
^{G 1 -III Y-IV R-} III G 2 -VIII G 1 -III Y-IV R-III G 2 -IX
G ¹ -III YV R-III G ² -IG ¹ -III YV R-III G ² -II
G ¹ -III YV R-III G ² -III G ¹ -III YV R-III G ² -IV
^{G 1 -III YV R-III G} 2 -VIII G 1 -III YV R-III G 2 -IX
G ¹ -III YI R-IV G ² -IG ¹ -III YI R-III G ² -II
G ¹ -III YI R-IV G ² -III G ¹ -III YI R-III G ² -IV
G ¹ -III YI R-IV G ² -VIII G ¹ -III YI R-III G ² -IX
G ¹ -III Y-II R-IV G ² -IG ¹ -III Y-II R-III G ² -II
G ¹ -III Y-II R-IV G ² -III G ¹ -III Y-II R-IV G ² -IV
^{G 1 -III Y-II R-} IV G 2 -VIII G 1 -III Y-II R-IV G 2 -IX
G ¹ -III Y-IV R-IV G ² -IG ¹ -III Y-IV R-IV G ² -II
G ¹ -III Y-IV R-IV G ² -III G ¹ -III Y-IV R-IV G ² -IV
^{G 1 -III Y-IV R-} IV G 2 -VIII G 1 -III Y-IV R-IV G 2 -IX
G ¹ -III YV R-IV G ² -IG ¹ -III YV R-IV G ² -II
G ¹ -III YV R-IV G ² -III G ¹ -III YV R-IV G ² -IV
^{G 1 -III YV R-IV G} 2 -VIII G 1 -III YV R-IV G 2 -IX
G ¹ -IV YI RI G ² -IG ¹ -IV YI RI G ² -II
G ¹ -IV YI RI G ² -III G ¹ -IV YI RI G ² -IV
G ¹ -IV YI RI G ² -VIII G ¹ -IV YI RI G ² -IX
G ¹ -IV Y-II RI G ² -IG ¹ -IV Y-II RI G ² -II
G ¹ -IV Y-II RI G ² -III G ¹ -IV Y-II RI G ² -IV
G ¹ -IV Y-II RI G ² -VIII G ¹ -IV Y-II RI G ² -IX
G ¹ -IV Y-IV RI G ² -IG ¹ -IV Y-IV RI G ² -II
G ¹ -IV Y-IV RI G ² -III G ¹ -IV Y-IV RI G ² -IV
G ¹ -IV Y-IV RI G ² -VIII G ¹ -IV Y-IV RI G ² -IX
G ¹ -IV YV RI G ² -IG ¹ -IV YV RI G ² -II
G ¹ -IV YV RI G ² -III G ¹ -IV YV RI G ² -IV
G ¹ -IV YV RI G ² -VIII G ¹ -IV YV RI G ² -IX
G ¹ -IV YI R-II G ² -IG ¹ -IV YI R-II G ² -II
G ¹ -IV YI R-II G ² -III G ¹ -IV YI R-II G ² -IV
G ¹ -IV YI R-II G ² -VIII G ¹ -IV YI R-II G ² -IX
G ¹ -IV Y-II R-II G ² -IG ¹ -IV Y-II R-II G ² -II
G ¹ -IV Y-II R-II G ² -III G ¹ -IV Y-II R-II G ² -IV
G ¹ -IV Y-II R-II G ² -VIII G ¹ -IV Y-II R-II G ² -IX
G ¹ -IV Y-IV R-II G ² -IG ¹ -IV Y-IV R-II G ² -II
G ¹ -IV Y-IV R-II G ² -III G ¹ -IV Y-IV R-II G ² -IV
G ¹ -IV Y-IV R-II G ² -VIII G ¹ -IV Y-IV R-II G ² -IX
G ¹ -IV YV R-II G ² -IG ¹ -IV YV R-II G ² -II
G ¹ -IV YV R-II G ² -III G ¹ -IV YV R-II G ² -IV
G ¹ -IV YV R-II G ² -VIII G ¹ -IV YV R-II G ² -IX
G ¹ -IV YI R-III G ² -IG ¹ -IV YI R-III G ² -II
G ¹ -IV YI R-III G ² -III G ¹ -IV YI R-III G ² -IV
G ¹ -IV YI R-III G ² -VIII G ¹ -IV YI R-III G ² -IX
G ¹ -IV Y-II R-III G ² -IG ¹ -IV Y-II R-III G ² -II
G ¹ -IV Y-II R-III G ² -III G ¹ -IV Y-II R-III G ² -IV
G ¹ -IV Y-II R-III G ² -VIII G ¹ -IV Y-II R-III G ² -IX
G ¹ -IV Y-IV R-III G ² -IG ¹ -IV Y-IV R-III G ² -II
G ¹ -IV Y-IV R-III G ² -III G ¹ -IV Y-IV R-III G ² -IV
G ¹ -IV Y-IV R-III G ² -VIII G ¹ -IV Y-IV R-III G ² -IX
G ¹ -IV YV R-III G ² -IG ¹ -IV YV R-III G ² -II
G ¹ -IV YV R-III G ² -III G ¹ -IV YV R-III G ² -IV
G ¹ -IV YV R-III G ² -VIII G ¹ -IV YV R-III G ² -IX
G ¹ -IV YI R-IV G ² -IG ¹ -IV YI R-III G ² -II
G ¹ -IV YI R-IV G ² -III G ¹ -IV YI R-III G ² -IV
G ¹ -IV YI R-IV G ² -VIII G ¹ -IV YI R-III G ² -IX
G ¹ -IV Y-II R-IV G ² -IG ¹ -IV Y-II R-III G ² -II
G ¹ -IV Y-II R-IV G ² -III G ¹ -IV Y-II R-IV G ² -IV
G ¹ -IV Y-II R-IV G ² -VIII G ¹ -IV Y-II R-IV G ² -IX
G ¹ -IV Y-IV R-IV G ² -IG ¹ -IV Y-IV R-IV G ² -II
G ¹ -IV Y-IV R-IV G ² -III G ¹ -IV Y-IV R-IV G ² -IV
G ¹ -IV Y-IV R-IV G ² -VIII G ¹ -IV Y-IV R-IV G ² -IX
G ¹ -IV YV R-IV G ² -IG ¹ -IV YV R-IV G ² -II
G ¹ -IV YV R-IV G ² -III G ¹ -IV YV R-IV G ² -IV
G ¹ -IV YV R-IV G ² -VIII G ¹ -IV YV R-IV G ² -IX
G ¹ -V YI RI G ² -IG ¹ -V YI RI G ² -II
G ¹ -V YI RI G ² -III G ¹ -V YI RI G ² -IV
G ¹ -V YI RI G ² -VIII G ¹ -V YI RI G ² -IX
G ¹ -V Y-II RI G ² -IG ¹ -V Y-II RI G ² -II
G ¹ -V Y-II RI G ² -III G ¹ -V Y-II RI G ² -IV
G ¹ -V Y-II RI G ² -VIII G ¹ -V Y-II RI G ² -IX
G ¹ -V Y-IV RI G ² -IG ¹ -V Y-IV RI G ² -II
G ¹ -V Y-IV RI G ² -III G ¹ -V Y-IV RI G ² -IV
G ¹ -V Y-IV RI G ² -VIII G ¹ -V Y-IV RI G ² -IX
G ¹ -V YV RI G ² -IG ¹ -V YV RI G ² -II
G ¹ -V YV RI G ² -III G ¹ -V YV RI G ² -IV
G ¹ -V YV RI G ² -VIII G ¹ -V YV RI G ² -IX
G ¹ -V YI R-II G ² -IG ¹ -V YI R-II G ² -II
G ¹ -V YI R-II G ² -III G ¹ -V YI R-II G ² -IV
G ¹ -V YI R-II G ² -VIII G ¹ -V YI R-II G ² -IX
G ¹ -V Y-II R-II G ² -IG ¹ -V Y-II R-II G ² -II
G ¹ -V Y-II R-II G ² -III G ¹ -V Y-II R-II G ² -IV
G ¹ -V Y-II R-II G ² -VIII G ¹ -V Y-II R-II G ² -IX
G ¹ -V Y-IV R-II G ² -IG ¹ -V Y-IV R-II G ² -II
G ¹ -V Y-IV R-II G ² -III G ¹ -V Y-IV R-II G ² -IV
G ¹ -V Y-IV R-II G ² -VIII G ¹ -V Y-IV R-II G ² -IX
G ¹ -V YV R-II G ² -IG ¹ -V YV R-II G ² -II
G ¹ -V YV R-II G ² -III G ¹ -V YV R-II G ² -IV
G ¹ -V YV R-II G ² -VIII G ¹ -V YV R-II G ² -IX
G ¹ -V YI R-III G ² -IG ¹ -V YI R-III G ² -II
G ¹ -V YI R-III G ² -III G ¹ -V YI R-III G ² -IV
G ¹ -V YI R-III G ² -VIII G ¹ -V YI R-III G ² -IX
G ¹ -V Y-II R-III G ² -IG ¹ -V Y-II R-III G ² -II
G ¹ -V Y-II R-III G ² -III G ¹ -V Y-II R-III G ² -IV
G ¹ -V Y-II R-III G ² -VIII G ¹ -V Y-II R-III G ² -IX
G ¹ -V Y-IV R-III G ² -IG ¹ -V Y-IV R-III G ² -II
G ¹ -V Y-IV R-III G ² -III G ¹ -V Y-IV R-III G ² -IV
G ¹ -V Y-IV R-III G ² -VIII G ¹ -V Y-IV R-III G ² -IX
G ¹ -V YV R-III G ² -IG ¹ -V YV R-III G ² -II
G ¹ -V YV R-III G ² -III G ¹ -V YV R-III G ² -IV
G ¹ -V YV R-III G ² -VIII G ¹ -V YV R-III G ² -IX
G ¹ -V YI R-IV G ² -IG ¹ -V YI R-III G ² -II
G ¹ -V YI R-IV G ² -III G ¹ -V YI R-III G ² -IV
G ¹ -V YI R-IV G ² -VIII G ¹ -V YI R-III G ² -IX
G ¹ -V Y-II R-IV G ² -IG ¹ -V Y-II R-III G ² -II
G ¹ -V Y-II R-IV G ² -III G ¹ -V Y-II R-IV G ² -IV
G ¹ -V Y-II R-IV G ² -VIII G ¹ -V Y-II R-IV G ² -IX
G ¹ -V Y-IV R-IV G ² -IG ¹ -V Y-IV R-IV G ² -II
G ¹ -V Y-IV R-IV G ² -III G ¹ -V Y-IV R-IV G ² -IV
G ¹ -V Y-IV R-IV G ² -VIII G ¹ -V Y-IV R-IV G ² -IX
G ¹ -V YV R-IV G ² -IG ¹ -V YV R-IV G ² -II
G ¹ -V YV R-IV G ² -III G ¹ -V YV R-IV G ² -IV
G ¹ -V YV R-IV G ² -VIII G ¹ -V YV R-IV G ² -IX
G ¹ -VII YI RI G ² -IG ¹ -VII YI RI G ² -II
G ¹ -VII YI RI G ² -III G ¹ -VII YI RI G ² -IV
^{G 1 -VII YI RI G 2 -VIII} G 1 -VII YI RI G 2 -IX
G ¹ -VII Y-II RI G ² -IG ¹ -VII Y-II RI G ² -II
G ¹ -VII Y-II RI G ² -III G ¹ -VII Y-II RI G ² -IV
^{G 1 -VII Y-II RI G} 2 -VIII G 1 -VII Y-II RI G 2 -IX
G ¹ -VII Y-IV RI G ² -IG ¹ -VII Y-IV RI G ² -II
G ¹ -VII Y-IV RI G ² -III G ¹ -VII Y-IV RI G ² -IV
^{G 1 -VII Y-IV RI G} 2 -VIII G 1 -VII Y-IV RI G 2 -IX
G ¹ -VII YV RI G ² -IG ¹ -VII YV RI G ² -II
G ¹ -VII YV RI G ² -III G ¹ -VII YV RI G ² -IV
^{G 1 -VII YV RI G 2 -VIII} G 1 -VII YV RI G 2 -IX
G ¹ -VII YI R-II G ² -IG ¹ -VII YI R-II G ² -II
G ¹ -VII YI R-II G ² -III G ¹ -VII YI R-II G ² -IV
^{G 1 -VII YI R-II G} 2 -VIII G 1 -VII YI R-II G 2 -IX
G ¹ -VII Y-II R-II G ² -IG ¹ -VII Y-II R-II G ² -II
G ¹ -VII Y-II R-II G ² -III G ¹ -VII Y-II R-II G ² -IV
G ¹ -VII Y-II R-II G ² -VIII G ¹ -VII Y-II R-II G ² -IX
G ¹ -VII Y-IV R-II G ² -IG ¹ -VII Y-IV R-II G ² -II
G ¹ -VII Y-IV R-II G ² -III G ¹ -VII Y-IV R-II G ² -IV
G ¹ -VII Y-IV R-II G ² -VIII G ¹ -VII Y-IV R-II G ² -IX
G ¹ -VII YV R-II G ² -IG ¹ -VII YV R-II G ² -II
G ¹ -VII YV R-II G ² -III G ¹ -VII YV R-II G ² -IV
^{G 1 -VII YV R-II G} 2 -VIII G 1 -VII YV R-II G 2 -IX
G ¹ -VII YI R-III G ² -IG ¹ -VII YI R-III G ² -II
G ¹ -VII YI R-III G ² -III G ¹ -VII YI R-III G ² -IV
^{G 1 -VII YI R-III G} 2 -VIII G 1 -VII YI R-III G 2 -IX
G ¹ -VII Y-II R-III G ² -IG ¹ -VII Y-II R-III G ² -II
G ¹ -VII Y-II R-III G ² -III G ¹ -VII Y-II R-III G ² -IV
G ¹ -VII Y-II R-III G ² -VIII G ¹ -VII Y-II R-III G ² -IX
G ¹ -VII Y-IV R-III G ² -IG ¹ -VII Y-IV R-III G ² -II
G ¹ -VII Y-IV R-III G ² -III G ¹ -VII Y-IV R-III G ² -IV
G ¹ -VII Y-IV R-III G ² -VIII G ¹ -VII Y-IV R-III G ² -IX
G ¹ -VII YV R-III G ² -IG ¹ -VII YV R-III G ² -II
G ¹ -VII YV R-III G ² -III G ¹ -VII YV R-III G ² -IV
^{G 1 -VII YV R-III G} 2 -VIII G 1 -VII YV R-III G 2 -IX
G ¹ -VII YI R-IV G ² -IG ¹ -VII YI R-III G ² -II
G ¹ -VII YI R-IV G ² -III G ¹ -VII YI R-III G ² -IV
G ¹ -VII YI R-IV G ² -VIII G ¹ -VII YI R-III G ² -IX
G ¹ -VII Y-II R-IV G ² -IG ¹ -VII Y-II R-III G ² -II
G ¹ -VII Y-II R-IV G ² -III G ¹ -VII Y-II R-IV G ² -IV
G ¹ -VII Y-II R-IV G ² -VIII G ¹ -VII Y-II R-IV G ² -IX
G ¹ -VII Y-IV R-IV G ² -IG ¹ -VII Y-IV R-IV G ² -II
G ¹ -VII Y-IV R-IV G ² -III G ¹ -VII Y-IV R-IV G ² -IV
G ¹ -VII Y-IV R-IV G ² -VIII G ¹ -VII Y-IV R-IV G ² -IX
G ¹ -VII YV R-IV G ² -IG ¹ -VII YV R-IV G ² -II
G ¹ -VII YV R-IV G ² -III G ¹ -VII YV R-IV G ² -IV
^{G 1 -VII YV R-IV G} 2 -VIII G 1 -VII YV R-IV G 2 -IX
G ¹ -VIII YI RI G ² -IG ¹ -VIII YI RI G ² -II
G ¹ -VIII YI RI G ² -III G ¹ -VIII YI RI G ² -IV
^{G 1 -VIII YI RI G 2 -VIII} G 1 -VIII YI RI G 2 -IX
G ¹ -VIII Y-II RI G ² -IG ¹ -VIII Y-II RI G ² -II
G ¹ -VIII Y-II RI G ² -III G ¹ -VIII Y-II RI G ² -IV
^{G 1 -VIII Y-II RI G} 2 -VIII G 1 -VIII Y-II RI G 2 -IX
G ¹ -VIII Y-IV RI G ² -IG ¹ -VIII Y-IV RI G ² -II
G ¹ -VIII Y-IV RI G ² -III G ¹ -VIII Y-IV RI G ² -IV
^{G 1 -VIII Y-IV RI G} 2 -VIII G 1 -VIII Y-IV RI G 2 -IX
G ¹ -VIII YV RI G ² -IG ¹ -VIII YV RI G ² -II
G ¹ -VIII YV RI G ² -III G ¹ -VIII YV RI G ² -IV
^{G 1 -VIII YV RI G 2 -VIII} G 1 -VIII YV RI G 2 -IX
G ¹ -VIII YI R-II G ² -IG ¹ -VIII YI R-II G ² -II
G ¹ -VIII YI R-II G ² -III G ¹ -VIII YI R-II G ² -IV
^{G 1 -VIII YI R-II G} 2 -VIII G 1 -VIII YI R-II G 2 -IX
G ¹ -VIII Y-II R-II G ² -IG ¹ -VIII Y-II R-II G ² -II
G ¹ -VIII Y-II R-II G ² -III G ¹ -VIII Y-II R-II G ² -IV
G ¹ -VIII Y-II R-II G ² -VIII G ¹ -VIII Y-II R-II G ² -IX
G ¹ -VIII Y-IV R-II G ² -IG ¹ -VIII Y-IV R-II G ² -II
G ¹ -VIII Y-IV R-II G ² -III G ¹ -VIII Y-IV R-II G ² -IV
G ¹ -VIII Y-IV R-II G ² -VIII G ¹ -VIII Y-IV R-II G ² -IX
G ¹ -VIII YV R-II G ² -IG ¹ -VIII YV R-II G ² -II
G ¹ -VIII YV R-II G ² -III G ¹ -VIII YV R-II G ² -IV
^{G 1 -VIII YV R-II G} 2 -VIII G 1 -VIII YV R-II G 2 -IX
G ¹ -VIII YI R-III G ² -IG ¹ -VIII YI R-III G ² -II
G ¹ -VIII YI R-III G ² -III G ¹ -VIII YI R-III G ² -IV
^{G 1 -VIII YI R-III G} 2 -VIII G 1 -VIII YI R-III G 2 -IX
G ¹ -VIII Y-II R-III G ² -IG ¹ -VIII Y-II R-III G ² -II
G ¹ -VIII Y-II R-III G ² -III G ¹ -VIII Y-II R-III G ² -IV
G ¹ -VIII Y-II R-III G ² -VIII G ¹ -VIII Y-II R-III G ² -IX
G ¹ -VIII Y-IV R-III G ² -IG ¹ -VIII Y-IV R-III G ² -II
G ¹ -VIII Y-IV R-III G ² -III G ¹ -VIII Y-IV R-III G ² -IV
G ¹ -VIII Y-IV R-III G ² -VIII G ¹ -VIII Y-IV R-III G ² -IX
G ¹ -VIII YV R-III G ² -IG ¹ -VIII YV R-III G ² -II
G ¹ -VIII YV R-III G ² -III G ¹ -VIII YV R-III G ² -IV
^{G 1 -VIII YV R-III G} 2 -VIII G 1 -VIII YV R-III G 2 -IX
G ¹ -VIII YI R-IV G ² -IG ¹ -VIII YI R-III G ² -II
G ¹ -VIII YI R-IV G ² -III G ¹ -VIII YI R-III G ² -IV
G ¹ -VIII YI R-IV G ² -VIII G ¹ -VIII YI R-III G ² -IX
G ¹ -VIII Y-II R-IV G ² -IG ¹ -VIII Y-II R-III G ² -II
G ¹ -VIII Y-II R-IV G ² -III G ¹ -VIII Y-II R-IV G ² -IV
G ¹ -VIII Y-II R-IV G ² -VIII G ¹ -VIII Y-II R-IV G ² -IX
G ¹ -VIII Y-IV R-IV G ² -IG ¹ -VIII Y-IV R-IV G ² -II
G ¹ -VIII Y-IV R-IV G ² -III G ¹ -VIII Y-IV R-IV G ² -IV
G ¹ -VIII Y-IV R-IV G ² -VIII G ¹ -VIII Y-IV R-IV G ² -IX
G ¹ -VIII YV R-IV G ² -IG ¹ -VIII YV R-IV G ² -II
G ¹ -VIII YV R-IV G ² -III G ¹ -VIII YV R-IV G ² -IV
^{G 1 -VIII YV R-IV G} 2 -VIII G 1 -VIII YV R-IV G 2 -IX
――――――――――――――――――――――――――――――――――――――
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), radish yellow 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), 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 blast Bacterial grain rot (Burkholderia gladioli, B. glumae), Bacterial fruit blotch (Acidovorax avenae subsp. Citrulli), Bacterial leaf blight (Acidovorax konjaci), Bacterial wilt (Ralrumonia soace) , Bacterial shot hole (Xanthomonas arboricola pv. Pruni, Pseudomonas syringae pv. Syringae, Brenneria nigrifluens), peach black spot Bacterial leaf spot (Xanthomonas arboricola pv. Pruni) vitians), cruciferous black rot (Xanthomonas campestris pv. campestris), soybean leaf burning Bacterial pustule (Xanthomonas ca mpestris pv. glycines), burdock black spot Bacterial spot (Xanthomonas campestris pv. nigromaculans), bell pepper 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), Japanese scab B acterial 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) 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.), Bluegrass (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) and other hominids (Hominidae), rabbits such as the European rabbit (Oryctolagus cuniculus) (Leporidae), chinchilla Long-tailed chinchilla (Chinchillalanigera) and other chinchiridae (Chinchillidae), guinea pigs Ciridae (Caviidae), Golden hamster (Mesocricetus auratus), Dungarian hamster (Phodopus sungorus), Mongolian gerbils such as Chinese hamster (Cricetulus griseus) House mo Use (Mus musculus), Rats such as Black rat (Rattus rattus) (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 (Felis silvestris catus), Dogs (Canis lupus familiaris), Dogs such as Red Fox (Vulpes vulpes), Canidae, Yo -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 (Daniorerio) and other carp family (Cyprinidae); (Pygocentrus nattereri), Neon tetra (Paracheirodon innesi), etc. Caracinaceae (Characidae), Shinanoyukimasa Maraena whitefish (Coregonus lavaretus maraena), Coho salmon (Oncorhynchus kisutsh), Rainbow trout Rainbow trout (Oncorhynchusmon) tshawytscha), Atlantic salmon (Salmo salar), Brown trout (Brown trout (Salmo trutta)), Salmonidae (Salmonidae); squamipinnis), Que Longtoot h grouper (Epinephelus bruneus), Mahata Convict 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 G ² , A, Y ¹ , Y ² , R ¹ , R ² , R ³ , R ⁴ , R ⁵ and m have the same meaning as described above. ] Or a salt thereof (for example, hydrochloride, hydrobromide, trifluoroacetate, p-toluenesulfonate, etc.) and formula (III) [wherein G ¹ represents the above meaning. . ], For example, Tetraheadron 2001, 57, 1551, Tetraheadron Lett. 1997, 38, 4853, Tetraheadron Letters. [Tetraheadron Lett.] 1994, Vol. 31, No. 5603, The Journal of Organic Chemistry [J. Org. Chem], 2004, Vol. 69, No. 55 were used. By reacting using the process conditions of the condensation reaction, the compound of formula (I) [wherein G ¹ , G ² , A, Y ¹ , Y ² , R ¹ , R ² , R ³ , R ⁴ , R ⁵ and m represents the same meaning as described above. This invention compound represented by this can be obtained.

  Some of the compounds represented by (III) used here are known compounds, and some of them are commercially available. Others can also be synthesized using known methods described in the literature.

  Manufacturing method B

Formula (Ia) wherein R ⁵ is a hydrogen atom in Formula (I) [wherein G ¹ , G ² , A, Y ¹ , Y ² , R ¹ , R ² , R ³ , R ⁴ and m are as defined above. Represents the same meaning. 1 equivalent and 1-10 equivalents of formula (IV) represented by the formula: [wherein R ⁵ is other than a hydrogen atom, —OH, C ₁ -C ₄ alkoxy and C ₁ -C ₄ haloalkoxy Wherein J ¹ represents a chlorine atom, a bromine atom, an iodine atom, a C ₁ -C ₄ alkylcarbonyloxy (eg, pivaloyloxy, etc.), a C ₁ -C ₄ alkyl sulfonate (eg, methanesulfonyloxy, etc.) C ₁ -C ₄ haloalkyl sulfonate (eg trifluoromethanesulfonyloxy etc.), aryl sulfonate (eg benzenesulfonyloxy, p-toluenesulfonyloxy etc.) or azolyl (eg imidazol-1-yl etc.) etc. Represents a leaving group. If necessary, using a polar solvent such as tert-butyl methyl ether, tetrahydrofuran, 1,4-dioxane, acetonitrile or N, N-dimethylformamide, and if necessary, a compound represented by formula (Ia) In the presence of a base such as 1 to 3 equivalents of sodium hydride, potassium tert-butoxide, potassium hydroxide, potassium carbonate, triethylamine or pyridine with respect to 1 equivalent of the compound represented, in a temperature range of 0 to 90 ° C. By reacting for 10 minutes to 24 hours, formula (I) [wherein G ¹ , G ² , A, Y ¹ , Y ² , R ¹ , R ² , R ³ , R ⁴ , R ⁵ and m are as defined above] Represents the same meaning. This invention compound represented by this can be obtained.

  Some of the compounds represented by formula (IV) used here are known compounds, and some of them can be purchased as commercial products. Others can also be synthesized according to general synthesis methods described in known literature.

  Manufacturing method C

Formula (V) [wherein G ¹ , A, Y ¹ , R ¹ , R ² , R ³ , R ⁴ and R ⁵ represent the same meaning as described above, J ² represents a chlorine atom, a bromine atom, an iodine atom, A compound represented by a C ₁ -C ₄ haloalkylsulfonate group (for example, a trifluoromethanesulfonyloxy group and the like) and formula (VI) [wherein G ² , Y ² and m represent the same meaning as described above; R ^a represents methyl or ethyl.], For example, tetrabutylammonium fluoride, etc. according to the method described in Synthetic communications 2012, 42, 1622 etc. In the presence of Sonogashira coupling reaction conditions to give a compound of formula (I) [wherein G ¹ , G ² , A, Y ¹ , Y ² , R ¹ , R ² , R ³ , R ⁴ , R ⁵ and m have the same meanings as described above.] 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, washed with water, poured into ice water, subjected to normal post-treatment such as extraction after organic solvent extraction, and the desired phenyl An acetylene-substituted amide compound can be obtained. Moreover, when the necessity for purification arises, it can be separated and purified by any purification method such as recrystallization, column chromatography, thin layer chromatography, liquid chromatography and the like.

  The compound represented by Formula (II) used in Production Method A can be synthesized, for example, as shown in Reaction Scheme 1.

  Reaction formula 1

Formula (VII) [wherein A, Y ¹ , R ¹ , R ² , R ³ , R ⁴ , R ⁵ and J ² represent the same meaning as described above. And a compound represented by formula (VI) [wherein G ² , Y ² , R ^a and m represent the same meaning as described above. And a compound represented by the formula (VIII) [wherein G ² , A, Y ¹ , Y ² , R ¹ , R ² , R ³ , R ⁴ , R ⁵ and m are as defined above. The compound represented by this can be obtained.

The compounds represented by the formula (VIII) thus obtained are, for example, European Patent Publication (EP 1,574,511 Publication), International Patent Application Publication (WO 2008/021927 Publication), International Patent Application Publication (WO 2010 / In accordance with the method described in Japanese Patent No. 075200) and the like, it is reacted with hydrochloric acid, hydrobromic acid, trifluoroacetic acid or the like to perform deprotection, whereby formula (II) [wherein G ² , A, Y ¹ , Y ² , R ¹ , R ² , R ³ , R ⁴ , R ⁵ and m represent the same meaning as described above. Or a salt thereof (for example, hydrochloride, hydrobromide, trifluoroacetate, etc.).

  Some of the compounds represented by formula (VII) used here are known compounds described in, for example, International Patent Application Publication (WO 2015/125824), and other compounds are also known. It can be synthesized according to the synthesis method for the compound or the reaction scheme 2.

  Reaction formula 2

Formula (IX) [wherein Y ¹ , R ¹ , R ² and J ² represent the same meaning as described above. ], For example, Synthetic Communications 2014, 44, 1600, Bioorganic & Medicinal Chemistry Letters [Bioorganic & Med. Chem. Lett] 2011, 21 In accordance with the method described in paragraph 1434, etc., formula (X) [wherein R ³ represents the same meaning as described above, and J ³ represents a chlorine atom, a bromine atom, or an iodine atom. Or a known Grignard reagent represented by the formula (XI) [wherein R ³ represents the above meaning. ] Is reacted with a known lithium reactant represented by formula (XII) [wherein A, Y ¹ , R ¹ , R ² , R ³ And J ² represents the same meaning as described above. The compound represented by this can be obtained.

By reacting the compound represented by the formula (XII) thus obtained with di-tert-butyl dicarbonate according to, for example, the method of International Patent Application Publication (WO2016 / 187384), In formula (VII), R ⁵ is a hydrogen atom (VIIa) [wherein A, Y ¹ , R ¹ , R ² , R ³ and J ² represent the same meaning as described above. The compound represented by this can be obtained.

  Some of the compounds represented by the formula (IX) used here are known compounds described in, for example, International Patent Application Publication (WO 2015/125824), etc. It can be synthesized using a known compound synthesis method.

  Some of the compounds represented by Formula (VI) used in Production Method C and Reaction Scheme 1 are known compounds, and others can be synthesized as in Reaction Scheme 3.

  Reaction formula 3

Formula (XIII) [wherein Y ² and m represent the same meaning as described above, and J ⁴ represents a chlorine atom, a bromine atom or an iodine atom. And a compound represented by formula (XIV) [wherein G ² represents the same meaning as described above, and J ⁵ represents a fluorine atom, a chlorine atom, or a bromine atom. ], For example, the method described in International Patent Application Publication (WO2013 / 064883), Journal of Medicinal Chemistry [J. Med. Chem.] 2014, 57, 3818 In accordance with the above, by reacting in the presence of a base such as potassium carbonate, or by reacting with a copper catalyst and a ligand such as picolinic acid, the formula (XV) [wherein G ² , Y ² , m and J ⁴ are Represents the same meaning as above. ] Can be obtained.

Next, the compound represented by the formula (XV) and the formula (XVI) [wherein ^Ra represents the same meaning as described above. The compound represented by formula (VI) is reacted with the compound under the general Sonogashira coupling reaction conditions described in, for example, International Patent Application Publication (WO 2008/093065). wherein, G ^2, Y ^2, m and R ^a are as defined above. The compound represented by this can be obtained.

  Some of the compounds represented by Formula (XIII), Formula (XIV), and Formula (XVI) used in Reaction Scheme 3 are known compounds, and some of them are commercially available. In addition, other compounds can be synthesized using a known compound synthesis method.

  Some of the compounds represented by the formula (V) used in the production method C are known compounds described in, for example, International Patent Application Publication (WO 2015/125824), and others are as shown in Reaction Scheme 4. Can be synthesized.

  Reaction formula 4

Formula (IX) [wherein A, Y ¹ , R ¹ , R ² and J ² represent the same meaning as described above. ], For example, in the presence of titanium (IV) tetraisopropoxide and boron trifluoride diethyl ether complex in accordance with the method described in Chemical Communications [Chem. By reacting with a reactant, formula (XVII) [wherein A, Y ¹ , R ¹ , R ² and J ² represent the same meaning as described above. The compound represented by this can be obtained.

The compound represented by the formula (XVII) thus obtained and the formula (XVIII) [wherein G ¹ represents the same meaning as described above, J ⁶ represents a chlorine atom, a bromine atom, a C ₁ -C ₄ alkyl. A carbonyloxy group (eg, pivaloyloxy). C ₁ -C ₄ alkoxycarbonyloxy group (e.g., iso-butyloxycarbonyl oxy) or represents an azolyl group (e.g., imidazol-1-yl). In the formula (V), R ³ and R ⁴ can be reacted with a compound represented by the general condensation conditions described in, for example, International Patent Application Publication (WO 2014/177473). Together form a ethylene chain to form a cyclopropane ring with the carbon atom to which R ³ and R ⁴ are bonded, and R ⁵ is a hydrogen atom [wherein G ¹ , Y ¹ , R ¹ , R ² and J ² represent the above meanings. 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 commercially available. Other methods are also described in literature, for example, Journal of Medicinal Chemistry [J. Med. Chem] 1991, 34, 1630, Tetraheadron Lett. 2003, 44. 4819, Journal of Medicinal Chemistry [J. Med. Chem] 1991, 34, 222, The Journal of Organic Chemistry [J. Org. Chem] 1989, 54, 5620 It can synthesize | combine using the method as described in a term etc.

  In each of these reactions, after the completion of the reaction, each of the production intermediates that will be 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 phenylacetylene-substituted amide compound represented by the formula (I) included in the present invention that can be produced using these methods include the structural formulas of [I] -1 to [I] -42 shown below. The compound represented by these is mentioned. However, the compounds represented by the structural formulas [I] -1 to [I] -42 are for illustrative purposes, and the phenylacetylene-substituted amide type compounds included in the present invention are limited to these. It is not a thing.

In the compounds represented by the structural formulas [I] -1 to [I] -42, A ¹ , Y ¹ , R ¹ , R ² , R ³ , R ⁴ , R ⁵ , Y ² , m and Examples of specific combinations of substituents represented by G ² include, for example, combinations shown in Table 2.

In the table, the description of Et represents ethyl, n-Pr represents normal propyl, i-Pr represents isopropyl, and the notation “-” in the column of substituent Y ² has a corresponding substituent. The number attached to each substituent represents that it corresponds to the substitution position indicated by the number in the structural formula of [I] -1 to [I] -42, and the substituent G notation and ^{G 2 -1-a~G 2 -4-} b in the ^second column, each represent a specific structure below,

For example, the notation (G ² -4-b) -6-Cl represents 6-chloro-quinoxalin-2-yl.

However, the combinations of substituents represented by A, Y ¹ , R ¹ , R ² , R ³ , R ⁴ , R ⁵ , Y ² , m2 and G ² shown in Table 2 are for illustration. Thus, combinations of the substituents in the structural formulas [I] -1 to [I] -42 are not limited to these.
Table 2
-------------------------------------------------- ------------------------------
AY ¹ R ¹ R ² R ³ R ⁴ R ⁵ Y ² m G ²
-------------------------------------------------- ------------------------------
N Cl HHHHH-0 G ² -1-a
N Cl HHHHH-0 (G ² -1-a) -4-Cl
N Cl HHHHH-0 (G ² -1-a) -4-CF ₃
N Cl HHHHH-0 (G ² -1-a) -2,4-Cl ₂
N Cl HHHHH-0 (G ² -1-a) -2-Cl ₄ -CF ₃
N Cl HHHHH-0 (G ² -1-c) -2,3,5,6-F ₄
N Cl HHHHH-0 (G ² -1-c) -2,3,5,6-Cl ₄
N Cl HHHHH-0 G ² -4-b
N Cl HHHHH-0 (G ² -4-b) -6-Cl
N Cl HHHHH-0 (G ² -4-b) -6-CF ₃
CH Cl HHHHH-0 G ² -1-a
CH Cl HHHHH-0 (G ² -1-a) -4-Cl
CH Cl HHHHH-0 (G ² -1-a) -4-CF ₃
CH Cl HHHHH-0 (G ² -1-a) -2,4-Cl ₂
CH Cl HHHHH-0 (G ² -1-a) -2-Cl ₄ -CF ₃
CH Cl HHHHH-0 (G ² -1-c) -2,3,5,6-F ₄
CH Cl HHHHH-0 (G ² -1-c) -2,3,5,6-Cl ₄
CH Cl HHHHH-0 G ² -4-b
CH Cl HHHHH-0 (G ² -4-b) -6-Cl
CH Cl HHHHH-0 (G ² -4-b) -6-CF ₃
N Cl FFHHH-0 G ² -1-a
N Cl FFHHH-0 (G ² -1-a) -4-Cl
N Cl FFHHH-0 (G ² -1-a) -4-CF ₃
N Cl FFHHH-0 (G ² -1-a) -2,4-Cl ₂
N Cl FFHHH-0 (G ² -1-a) -2-Cl ₄ -CF ₃
N Cl FFHHH-0 (G ² -1-c) -2,3,5,6-F ₄
N Cl FFHHH-0 (G2-1-c) -2,3,5,6-Cl ₄
N Cl FFHHH-0 G ² -4-b
N Cl FFHHH-0 (G ² -4-b) -6-Cl
N Cl FFHHH-0 (G ² -4-b) -6-CF ₃
CH Cl FFHHH-0 G ² -1-a
CH Cl FFHHH-0 (G ² -1-a) -4-Cl
CH Cl FFHHH-0 (G ² -1-a) -4-CF ₃
CH Cl FFHHH-0 (G ² -1-a) -2,4-Cl ₂
CH Cl FFHHH-0 (G ² -1-a) -2-Cl ₄ -CF ₃
CH Cl FFHHH-0 (G ² -1-c) -2,3,5,6-F ₄
CH Cl FFHHH-0 (G ² -1-c) -2,3,5,6-Cl ₄
CH Cl FFHHH-0 G ² -4-b
CH Cl FFHHH-0 (G ² -4-b) -6-Cl
CH Cl FFHHH-0 (G ² -4-b) -6-CF ₃
N Cl FF CH ₃ HH-0 G ² -1-a
N Cl FF CH ₃ HH-0 (G ² -1-a) -4-Cl
N Cl FF CH ₃ HH-0 (G ² -1-a) -4-CF ₃
N Cl FF CH ₃ HH-0 (G ² -1-a) -2,4-Cl ₂
N Cl FF CH ₃ HH-0 (G ² -1-a) -2-Cl ₄ -CF ₃
N Cl FF CH ₃ HH-0 (G ² -1-c) -2,3,5,6-F ₄
N Cl FF CH ₃ HH-0 (G ² -1-c) -2,3,5,6-Cl ₄
N Cl FF CH ₃ HH-0 G ² -4-b
N Cl FF CH ₃ HH-0 (G ² -4-b) -6-Cl
N Cl FF CH ₃ HH-0 (G ² -4-b) -6-CF ₃
CH Cl FF CH ₃ HH-0 G ² -1-a
CH Cl FF CH ₃ HH-0 (G ² -1-a) -4-Cl
CH Cl FF CH ₃ HH-0 (G ² -1-a) -4-CF ₃
CH Cl FF CH ₃ HH-0 (G ² -1-a) -2,4-Cl ₂
CH Cl FF CH ₃ HH-0 (G ² -1-a) -2-Cl ₄ -CF ₃
CH Cl FF CH ₃ HH-0 (G ² -1-c) -2,3,5,6-F ₄
CH Cl FF CH ₃ HH-0 (G ² -1-c) -2,3,5,6-Cl ₄
CH Cl FF CH ₃ HH-0 G ² -4-b
CH Cl FF CH ₃ HH-0 (G ² -4-b) -6-Cl
CH Cl FF CH ₃ HH-0 (G ² -4-b) -6-CF ₃
N Cl HH CH ₃ HH-0 G ² -1-a
N Cl HH CH ₃ HH-0 (G ² -1-a) -4-Cl
N Cl HH CH ₃ HH-0 (G ² -1-a) -4-CF ₃
N Cl HH CH ₃ HH-0 (G ² -1-a) -2,4-Cl ₂
N Cl HH CH ₃ HH-0 (G ² -1-a) -2-Cl ₄ -CF ₃
N Cl HH CH ₃ HH-0 (G ² -1-c) -2,3,5,6-F ₄
N Cl HH CH ₃ HH-0 (G ² -1-c) -2,3,5,6-Cl ₄
N Cl HH CH ₃ HH-0 G ² -4-b
N Cl HH CH ₃ HH-0 (G ² -4-b) -6-Cl
N Cl HH CH ₃ HH-0 (G ² -4-b) -6-CF ₃
CH Cl HH CH ₃ HH-0 G ² -1-a
CH Cl HH CH ₃ HH-0 (G ² -1-a) -4-Cl
CH Cl HH CH ₃ HH-0 (G ² -1-a) -4-CF ₃
CH Cl HH CH ₃ HH-0 (G ² -1-a) -2,4-Cl ₂
CH Cl HH CH ₃ HH-0 (G ² -1-a) -2-Cl ₄ -CF ₃
CH Cl HH CH ₃ HH-0 (G ² -1-c) -2,3,5,6-F ₄
CH Cl HH CH ₃ HH-0 (G ² -1-c) -2,3,5,6-Cl ₄
CH Cl HH CH ₃ HH-0 G ² -4-b
CH Cl HH CH ₃ HH-0 (G ² -4-b) -6-Cl
CH Cl HH CH ₃ HH-0 (G ² -4-b) -6-CF ₃
N Cl OCH ₃ H CH ₃ HH-0 G ² -1-a
N Cl OCH ₃ H CH ₃ HH-0 (G ² -1-a) -4-Cl
N Cl OCH ₃ H CH ₃ HH-0 (G ² -1-a) -4-CF ₃
N Cl OCH ₃ H CH ₃ HH-0 (G ² -1-a) -2,4-Cl ₂
N Cl OCH ₃ H CH ₃ HH-0 (G ² -1-a) -2-Cl ₄ -CF ₃
N Cl OCH ₃ H CH ₃ HH-0 (G ² -1-c) -2,3,5,6-F ₄
N Cl OCH ₃ H CH ₃ HH-0 (G ² -1-c) -2,3,5,6-Cl ₄
N Cl OCH ₃ H CH ₃ HH-0 G ² -4-b
N Cl OCH ₃ H CH ₃ HH-0 (G ² -4-b) -6-Cl
N Cl OCH ₃ H CH ₃ HH-0 (G ² -4-b) -6-CF ₃
CH Cl OCH ₃ H CH ₃ HH-0 G ² -1-a
CH Cl OCH ₃ H CH ₃ HH-0 (G ² -1-a) -4-Cl
CH Cl OCH ₃ H CH ₃ HH-0 (G ² -1-a) -4-CF ₃
CH Cl OCH ₃ H CH ₃ HH-0 (G ² -1-a) -2,4-Cl ₂
CH Cl OCH ₃ H CH ₃ HH-0 (G ² -1-a) -2-Cl ₄ -CF ₃
CH Cl OCH ₃ H CH ₃ HH-0 (G ² -1-c) -2,3,5,6-F ₄
CH Cl OCH ₃ H CH ₃ HH-0 (G ² -1-c) -2,3,5,6-Cl ₄
CH Cl OCH ₃ H CH ₃ HH-0 G ² -4-b
CH Cl OCH ₃ H CH ₃ HH-0 (G ² -4-b) -6-Cl
CH Cl OCH ₃ H CH ₃ HH-0 (G ² -4-b) -6-CF ₃
N Cl CH ₃ HHHH-0 G ² -1-a
N Cl CH ₃ HHHH-0 (G ² -1-a) -4-Cl
N Cl CH ₃ HHHH-0 (G ² -1-a) -4-CF ₃
N Cl CH ₃ HHHH-0 (G ² -1-a) -2,4-Cl ₂
N Cl CH ₃ HHHH-0 (G ² -1-a) -2-Cl ₄ -CF ₃
N Cl CH ₃ HHHH-0 (G ² -1-c) -2,3,5,6-F ₄
N Cl CH ₃ HHHH-0 (G ² -1-c) -2,3,5,6-Cl ₄
N Cl CH ₃ HHHH-0 G ² -4-b
N Cl CH ₃ HHHH-0 (G ² -4-b) -6-Cl
N Cl CH ₃ HHHH-0 (G ² -4-b) -6-CF ₃
CH Cl CH ₃ HHHH-0 G ² -1-a
CH Cl CH ₃ HHHH-0 (G ² -1-a) -4-Cl
CH Cl CH ₃ HHHH-0 (G ² -1-a) -4-CF ₃
CH Cl CH ₃ HHHH-0 (G ² -1-a) -2,4-Cl ₂
CH Cl CH ₃ HHHH-0 (G ² -1-a) -2-Cl ₄ -CF ₃
CH Cl CH ₃ HHHH-0 (G ² -1-c) -2,3,5,6-F ₄
CH Cl CH ₃ HHHH-0 (G ² -1-c) -2,3,5,6-Cl ₄
CH Cl CH ₃ HHHH-0 G ² -4-b
CH Cl CH ₃ HHHH-0 (G ² -4-b) -6-Cl
CH Cl CH ₃ HHHH-0 (G ² -4-b) -6-CF ₃
N Cl OCH ₃ HHHH-0 G ² -1-a
N Cl OCH ₃ HHHH-0 (G ² -1-a) -4-Cl
N Cl OCH ₃ HHHH-0 (G ² -1-a) -4-CF ₃
N Cl OCH ₃ HHHH-0 (G ² -1-a) -2,4-Cl ₂
N Cl OCH ₃ HHHH-0 (G ² -1-a) -2-Cl ₄ -CF ₃
N Cl OCH ₃ HHHH-0 (G ² -1-c) -2,3,5,6-F ₄
N Cl OCH ₃ HHHH-0 (G ² -1-c) -2,3,5,6-Cl ₄
N Cl OCH ₃ HHHH-0 G ² -4-b
N Cl OCH ₃ HHHH-0 (G ² -4-b) -6-Cl
N Cl OCH ₃ HHHH-0 (G ² -4-b) -6-CF ₃
CH Cl OCH ₃ HHHH-0 G ² -1-a
CH Cl OCH ₃ HHHH-0 (G ² -1-a) -4-Cl
CH Cl OCH ₃ HHHH-0 (G ² -1-a) -4-CF ₃
CH Cl OCH ₃ HHHH-0 (G ² -1-a) -2,4-Cl ₂
CH Cl OCH ₃ HHHH-0 (G ² -1-a) -2-Cl ₄ -CF ₃
CH Cl OCH ₃ HHHH-0 (G ² -1-c) -2,3,5,6-F ₄
CH Cl OCH ₃ HHHH-0 (G ² -1-c) -2,3,5,6-Cl ₄
CH Cl OCH ₃ HHHH-0 G ² -4-b
CH Cl OCH ₃ HHHH-0 (G ² -4-b) -6-Cl
CH Cl OCH ₃ HHHH-0 (G ² -4-b) -6-CF ₃
N Cl -CH ₂ CH ₂ -HHH-0 G ² -1-a
N Cl -CH ₂ CH ₂ -HHH-0 (G ² -1-a) -4-Cl
N Cl -CH ₂ CH ₂ -HHH-0 (G ² -1-a) -4-CF ₃
N Cl -CH ₂ CH ₂ -HHH-0 (G ² -1-a) -2,4-Cl ₂
N Cl -CH ₂ CH ₂ -HHH-0 (G ² -1-a) -2-Cl ₄ -CF ₃
N Cl -CH ₂ CH ₂ -HHH-0 (G ² -1-c) -2,3,5,6-F ₄
N Cl -CH ₂ CH ₂ -HHH-0 (G ² -1-c) -2,3,5,6-Cl ₄
N Cl -CH ₂ CH ₂ -HHH-0 G ² -4-b
N Cl -CH ₂ CH ₂ -HHH-0 (G ² -4-b) -6-Cl
N Cl -CH ₂ CH ₂ -HHH-0 (G ² -4-b) -6-CF ₃
CH Cl -CH ₂ CH ₂ -HHH-0 G ² -1-a
CH Cl -CH ₂ CH ₂ -HHH-0 (G ² -1-a) -4-Cl
CH Cl -CH ₂ CH ₂ -HHH-0 (G ² -1-a) -4-CF ₃
CH Cl -CH ₂ CH ₂ -HHH-0 (G ² -1-a) -2,4-Cl ₂
CH Cl -CH ₂ CH ₂ -HHH-0 (G ² -1-a) -2-Cl ₄ -CF ₃
CH Cl -CH ₂ CH ₂ -HHH-0 (G ² -1-c) -2,3,5,6-F ₄
CH Cl -CH ₂ CH ₂ -HHH-0 (G ² -1-c) -2,3,5,6-Cl ₄
CH Cl -CH ₂ CH ₂ -HHH-0 G ² -4-b
CH Cl -CH ₂ CH ₂ -HHH-0 (G ² -4-b) -6-Cl
CH Cl -CH ₂ CH ₂ -HHH-0 (G ² -4-b) -6-CF ₃
N Cl HH -CH ₂ CH ₂ -H-0 G ² -1-a
N Cl HH -CH ₂ CH ₂ -H-0 (G ² -1-a) -4-Cl
N Cl HH -CH ₂ CH ₂ -H-0 (G ² -1-a) -4-CF ₃
N Cl HH -CH ₂ CH ₂ -H-0 (G ² -1-a) -2,4-Cl ₂
N Cl HH -CH ₂ CH ₂ -H-0 (G ² -1-a) -2-Cl ₄ -CF ₃
N Cl HH -CH ₂ CH ₂ -H-0 (G ² -1-c) -2,3,5,6-F ₄
N Cl HH -CH ₂ CH ₂ -H-0 (G ² -1-c) -2,3,5,6-Cl ₄
N Cl HH -CH ₂ CH ₂ -H-0 G ² -4-b
N Cl HH -CH ₂ CH ₂ -H-0 (G ² -4-b) -6-Cl
N Cl HH -CH ₂ CH ₂ -H-0 (G ² -4-b) -6-CF ₃
CH Cl HH -CH ₂ CH ₂ -H-0 G ² -1-a
CH Cl HH -CH ₂ CH ₂ -H-0 (G ² -1-a) -4-Cl
CH Cl HH -CH ₂ CH ₂ -H-0 (G ² -1-a) -4-CF ₃
CH Cl HH -CH ₂ CH ₂ -H-0 (G ² -1-a) -2,4-Cl ₂
CH Cl HH -CH ₂ CH ₂ -H-0 (G ² -1-a) -2-Cl ₄ -CF ₃
CH Cl HH -CH ₂ CH ₂ -H-0 (G ² -1-c) -2,3,5,6-F ₄
CH Cl HH -CH ₂ CH ₂ -H-0 (G ² -1-c) -2,3,5,6-Cl ₄
CH Cl HH -CH ₂ CH ₂ -H-0 G ² -4-b
CH Cl HH -CH ₂ CH ₂ -H-0 (G ² -4-b) -6-Cl
CH Cl HH -CH ₂ CH ₂ -H-0 (G ² -4-b) -6-CF ₃
NF OCH ₃ H CH ₃ HH-0 (G ² -1-a) -4-CF ₃
NF OCH ₃ H CH ₃ HH-0 (G ² -1-a) -2,4-Cl ₂
NF OCH ₃ H CH ₃ HH-0 (G ² -1-a) -2-Cl ₄ -CF ₃
NF OCH ₃ H CH ₃ HH-0 (G ² -4-b) -6-Cl
CH F OCH ₃ H CH ₃ HH-0 (G ² -1-a) -4-CF ₃
CH F OCH ₃ H CH ₃ HH-0 (G ² -1-a) -2,4-Cl ₂
CH F OCH ₃ H CH ₃ HH-0 (G ² -1-a) -2-Cl ₄ -CF ₃
CH F OCH ₃ H CH ₃ HH-0 (G ² -4-b) -6-Cl
NFFFHHH-0 (G ² -1-a) -4-CF ₃
NFFFHHH-0 (G ² -1-a) -2,4-Cl ₂
NFFFHHH-0 (G ² -1-a) -2-Cl ₄ -CF ₃
NFFFHHH-0 (G ² -4-b) -6-Cl
CH FFFHHH-0 (G ² -1-a) -4-CF ₃
CH FFFHHH-0 (G ² -1-a) -2,4-Cl ₂
CH FFFHHH-0 (G ² -1-a) -2-Cl ₄ -CF ₃
CH FFFHHH-0 (G ² -4-b) -6-Cl
NFFF CH ₃ HH-0 (G ² -1-a) -4-CF ₃
NFFF CH ₃ HH-0 (G ² -1-a) -2,4-Cl ₂
NFFF CH ₃ HH-0 (G ² -1-a) -2-Cl ₄ -CF ₃
NFFF CH ₃ HH-0 (G ² -4-b) -6-Cl
CH FFF CH ₃ HH-0 (G ² -1-a) -4-CF ₃
CH FFF CH ₃ HH-0 (G ² -1-a) -2,4-Cl ₂
CH FFF CH ₃ HH-0 (G ² -1-a) -2-Cl ₄ -CF ₃
CH FFF CH ₃ HH-0 (G ² -4-b) -6-Cl
N CH ₃ OCH ₃ H CH ₃ HH-0 (G ² -1-a) -4-CF ₃
N CH ₃ OCH ₃ H CH ₃ HH-0 (G ² -1-a) -2,4-Cl ₂
N CH ₃ OCH ₃ H CH ₃ HH-0 (G ² -1-a) -2-Cl ₄ -CF ₃
N CH ₃ OCH ₃ H CH ₃ HH-0 (G ² -4-b) -6-Cl
CH CH ₃ OCH ₃ H CH ₃ HH-0 (G ² -1-a) -4-CF ₃
CH CH ₃ OCH ₃ H CH ₃ HH-0 (G ² -1-a) -2,4-Cl ₂
CH CH ₃ OCH ₃ H CH ₃ HH-0 (G ² -1-a) -2-Cl ₄ -CF ₃
CH CH ₃ OCH ₃ H CH ₃ HH-0 (G ² -4-b) -6-Cl
N CH ₃ FFHHH-0 (G ² -1-a) -4-CF ₃
N CH ₃ FFHHH-0 (G ² -1-a) -2,4-Cl ₂
N CH ₃ FFHHH-0 (G ² -1-a) -2-Cl ₄ -CF ₃
N CH ₃ FFHHH-0 (G ² -4-b) -6-Cl
CH CH ₃ FFHHH-0 (G ² -1-a) -4-CF ₃
CH CH ₃ FFHHH-0 (G ² -1-a) -2,4-Cl ₂
CH CH ₃ FFHHH-0 (G ² -1-a) -2-Cl ₄ -CF ₃
CH CH ₃ FFHHH-0 (G ² -4-b) -6-Cl
N CH ₃ FF CH ₃ HH-0 (G ² -1-a) -4-CF ₃
N CH ₃ FF CH ₃ HH-0 (G ² -1-a) -2,4-Cl ₂
N CH ₃ FF CH ₃ HH-0 (G ² -1-a) -2-Cl ₄ -CF ₃
N CH ₃ FF CH ₃ HH-0 (G ² -4-b) -6-Cl
CH CH ₃ FF CH ₃ HH-0 (G ² -1-a) -4-CF ₃
CH CH ₃ FF CH ₃ HH-0 (G ² -1-a) -2,4-Cl ₂
CH CH ₃ FF CH ₃ HH-0 (G ² -1-a) -2-Cl ₄ -CF ₃
CH CH ₃ FF CH ₃ HH-0 (G ² -4-b) -6-Cl
_{N Cl FFHH CH 3 - 0 (} G 2 -1-a) -4-CF 3
_{N Cl FFHH CH 3 - 0 (} G 2 -1-a) -2,4-Cl 2
_{N Cl FFHH CH 3 - 0 (} G 2 -1-a) -2-Cl 4 -CF 3
_{N Cl FFHH CH 3 - 0 (} G 2 -4-b) -6-Cl
_{CH Cl FFHH CH 3 - 0 (} G 2 -1-a) -4-CF 3
_{CH Cl FFHH CH 3 - 0 (} G 2 -1-a) -2,4-Cl 2
_{CH Cl FFHH CH 3 - 0 (} G 2 -1-a) -2-Cl 4 -CF 3
_{CH Cl FFHH CH 3 - 0 (} G 2 -4-b) -6-Cl
N Cl FFHH Et-0 (G ² -1-a) -4-CF ₃
N Cl FFHH Et-0 (G ² -1-a) -2,4-Cl ₂
N Cl FFHH Et-0 (G ² -1-a) -2-Cl ₄ -CF ₃
N Cl FFHH Et-0 (G ² -4-b) -6-Cl
CH Cl FFHH Et-0 (G ² -1-a) -4-CF ₃
CH Cl FFHH Et-0 (G ² -1-a) -2,4-Cl ₂
CH Cl FFHH Et-0 (G ² -1-a) -2-Cl ₄ -CF ₃
CH Cl FFHH Et-0 (G ² -4-b) -6-Cl
N Cl FFHH n-Pr-0 (G ² -1-a) -4-CF ₃
N Cl FFHH n-Pr-0 (G ² -1-a) -2,4-Cl ₂
N Cl FFHH n-Pr-0 (G ² -1-a) -2-Cl ₄ -CF ₃
N Cl FFHH n-Pr-0 (G ² -4-b) -6-Cl
CH Cl FFHH n-Pr-0 (G ² -1-a) -4-CF ₃
CH Cl FFHH n-Pr-0 (G ² -1-a) -2,4-Cl ₂
CH Cl FFHH n-Pr-0 (G ² -1-a) -2-Cl ₄ -CF ₃
CH Cl FFHH n-Pr-0 (G ² -4-b) -6-Cl
_{N Cl FFHH CH 2 OCH 3 -} 0 (G 2 -1-a) -4-CF 3
_{N Cl FFHH CH 2 OCH 3 -} 0 (G 2 -1-a) -2,4-Cl 2
_{N Cl FFHH CH 2 OCH 3 -} 0 (G 2 -1-a) -2-Cl 4 -CF 3
_{N Cl FFHH CH 2 OCH 3 -} 0 (G 2 -4-b) -6-Cl
_{CH Cl FFHH CH 2 OCH 3 -} 0 (G 2 -1-a) -4-CF 3
_{CH Cl FFHH CH 2 OCH 3 -} 0 (G 2 -1-a) -2,4-Cl 2
_{CH Cl FFHH CH 2 OCH 3 -} 0 (G 2 -1-a) -2-Cl 4 -CF 3
_{CH Cl FFHH CH 2 OCH 3 -} 0 (G 2 -4-b) -6-Cl
N Cl FFHH CH ₂ CN-0 (G ² -1-a) -4-CF ₃
N Cl FFHH CH ₂ CN-0 (G ² -1-a) -2,4-Cl ₂
N Cl FFHH CH ₂ CN-0 (G ² -1-a) -2-Cl ₄ -CF ₃
N Cl FFHH CH ₂ CN-0 (G ² -4-b) -6-Cl
CH Cl FFHH CH ₂ CN-0 (G ² -1-a) -4-CF ₃
CH Cl FFHH CH ₂ CN-0 (G ² -1-a) -2,4-Cl ₂
CH Cl FFHH CH ₂ CN-0 (G ² -1-a) -2-Cl ₄ -CF ₃
CH Cl FFHH CH ₂ CN-0 (G ² -4-b) -6-Cl
N Cl FFHH CH ₂ C≡CH-0 (G ² -1-a) -4-CF ₃
N Cl FFHH CH ₂ C≡CH-0 (G ² -1-a) -2,4-Cl ₂
N Cl FFHH CH ₂ C≡CH-0 (G ² -1-a) -2-Cl ₄ -CF ₃
N Cl FFHH CH ₂ C≡CH-0 (G ² -4-b) -6-Cl
CH Cl FFHH CH ₂ C≡CH-0 (G ² -1-a) -4-CF ₃
CH Cl FFHH CH ₂ C≡CH-0 (G ² -1-a) -2,4-Cl ₂
CH Cl FFHH CH ₂ C≡CH-0 (G ² -1-a) -2-Cl ₄ -CF ₃
CH Cl FFHH CH ₂ C≡CH-0 (G ² -4-b) -6-Cl
_{N Cl FFHHC (O) CH 3} - 0 (G 2 -1-a) -4-CF 3
_{N Cl FFHHC (O) CH 3} - 0 (G 2 -1-a) -2,4-Cl 2
_{N Cl FFHHC (O) CH 3} - 0 (G 2 -1-a) -2-Cl 4 -CF 3
_{N Cl FFHHC (O) CH 3} - 0 (G 2 -4-b) -6-Cl
_{CH Cl FFHHC (O) CH 3} - 0 (G 2 -1-a) -4-CF 3
_{CH Cl FFHHC (O) CH 3} - 0 (G 2 -1-a) -2,4-Cl 2
_{CH Cl FFHHC (O) CH 3} - 0 (G 2 -1-a) -2-Cl 4 -CF 3
_{CH Cl FFHHC (O) CH 3} - 0 (G 2 -4-b) -6-Cl
_{N Cl FFHHC (O) OCH 3} - 0 (G 2 -1-a) -4-CF 3
_{N Cl FFHHC (O) OCH 3} - 0 (G 2 -1-a) -2,4-Cl 2
_{N Cl FFHHC (O) OCH 3} - 0 (G 2 -1-a) -2-Cl 4 -CF 3
_{N Cl FFHHC (O) OCH 3} - 0 (G 2 -4-b) -6-Cl
_{CH Cl FFHHC (O) OCH 3} - 0 (G 2 -1-a) -4-CF 3
_{CH Cl FFHHC (O) OCH 3} - 0 (G 2 -1-a) -2,4-Cl 2
_{CH Cl FFHHC (O) OCH 3} - 0 (G 2 -1-a) -2-Cl 4 -CF 3
_{CH Cl FFHHC (O) OCH 3} - 0 (G 2 -4-b) -6-Cl
N Cl HHHHH 2-F 1 (G ² -1-a) -4-CF ₃
N Cl HHHHH 2-F 1 (G ² -1-a) -2,4-Cl ₂
N Cl HHHHH 2-F 1 (G ² -1-a) -2-Cl ₄ -CF ₃
N Cl HHHHH 2-F 1 (G ² -4-b) -6-Cl
CH Cl HHHHH 2-F 1 (G ² -1-a) -4-CF ₃
CH Cl HHHHH 2-F 1 (G ² -1-a) -2,4-Cl ₂
CH Cl HHHHH 2-F 1 (G ² -1-a) -2-Cl ₄ -CF ₃
CH Cl HHHHH 2-F 1 (G ² -4-b) -6-Cl
N Cl HH CH ₃ HH 2-F 1 (G ² -1-a) -4-CF ₃
N Cl HH CH ₃ HH 2-F 1 (G ² -1-a) -2,4-Cl ₂
N Cl HH CH ₃ HH 2-F 1 (G ² -1-a) -2-Cl ₄ -CF ₃
N Cl HH CH ₃ HH 2-F 1 (G ² -4-b) -6-Cl
CH Cl HH CH ₃ HH 2-F 1 (G ² -1-a) -4-CF ₃
CH Cl HH CH ₃ HH 2-F 1 (G ² -1-a) -2,4-Cl ₂
CH Cl HH CH ₃ HH 2-F 1 (G ² -1-a) -2-Cl ₄ -CF ₃
CH Cl HH CH ₃ HH 2-F 1 (G ² -4-b) -6-Cl
N Cl OCH ₃ H CH ₃ HH 2-F 1 (G ² -1-a) -4-CF ₃
N Cl OCH ₃ H CH ₃ HH 2-F 1 (G ² -1-a) -2,4-Cl ₂
N Cl OCH ₃ H CH ₃ HH 2-F 1 (G ² -1-a) -2-Cl ₄ -CF ₃
N Cl OCH ₃ H CH ₃ HH 2-F 1 (G ² -4-b) -6-Cl
CH Cl OCH ₃ H CH ₃ HH 2-F 1 (G ² -1-a) -4-CF ₃
CH Cl OCH ₃ H CH ₃ HH 2-F 1 (G ² -1-a) -2,4-Cl ₂
CH Cl OCH ₃ H CH ₃ HH 2-F 1 (G ² -1-a) -2-Cl ₄ -CF ₃
CH Cl OCH ₃ H CH ₃ HH 2-F 1 (G ² -4-b) -6-Cl
N Cl FFHHH 2-F 1 (G ² -1-a) -4-CF ₃
N Cl FFHHH 2-F 1 (G ² -1-a) -2,4-Cl ₂
N Cl FFHHH 2-F 1 (G ² -1-a) -2-Cl ₄ -CF ₃
N Cl FFHHH 2-F 1 (G ² -4-b) -6-Cl
CH Cl FFHHH 2-F 1 (G ² -1-a) -4-CF ₃
CH Cl FFHHH 2-F 1 (G ² -1-a) -2,4-Cl ₂
CH Cl FFHHH 2-F 1 (G ² -1-a) -2-Cl ₄ -CF ₃
CH Cl FFHHH 2-F 1 (G ² -4-b) -6-Cl
N Cl FF CH ₃ HH 2-F 1 (G ² -1-a) -4-CF ₃
N Cl FF CH ₃ HH 2-F 1 (G ² -1-a) -2,4-Cl ₂
N Cl FF CH ₃ HH 2-F 1 (G ² -1-a) -2-Cl ₄ -CF ₃
N Cl FF CH ₃ HH 2-F 1 (G ² -4-b) -6-Cl
CH Cl FF CH ₃ HH 2-F 1 (G ² -1-a) -4-CF ₃
CH Cl FF CH ₃ HH 2-F 1 (G ² -1-a) -2,4-Cl ₂
CH Cl FF CH ₃ HH 2-F 1 (G ² -1-a) -2-Cl ₄ -CF ₃
CH Cl FF CH ₃ HH 2-F 1 (G ² -4-b) -6-Cl
N Cl HHHHH 3-F 1 (G ² -1-a) -4-CF ₃
N Cl HHHHH 3-F 1 (G ² -1-a) -2,4-Cl ₂
N Cl HHHHH 3-F 1 (G ² -1-a) -2-Cl ₄ -CF ₃
N Cl HHHHH 3-F 1 (G ² -4-b) -6-Cl
CH Cl HHHHH 3-F 1 (G ² -1-a) -4-CF ₃
CH Cl HHHHH 3-F 1 (G ² -1-a) -2,4-Cl ₂
CH Cl HHHHH 3-F 1 (G ² -1-a) -2-Cl ₄ -CF ₃
CH Cl HHHHH 3-F 1 (G ² -4-b) -6-Cl
N Cl HH CH ₃ HH 3-F 1 (G ² -1-a) -4-CF ₃
N Cl HH CH ₃ HH 3-F 1 (G ² -1-a) -2,4-Cl ₂
N Cl HH CH ₃ HH 3-F 1 (G ² -1-a) -2-Cl ₄ -CF ₃
N Cl HH CH ₃ HH 3-F 1 (G ² -4-b) -6-Cl
CH Cl HH CH ₃ HH 3-F 1 (G ² -1-a) -4-CF ₃
CH Cl HH CH ₃ HH 3-F 1 (G ² -1-a) -2,4-Cl ₂
CH Cl HH CH ₃ HH 3-F 1 (G ² -1-a) -2-Cl ₄ -CF ₃
CH Cl HH CH ₃ HH 3-F 1 (G ² -4-b) -6-Cl
N Cl OCH ₃ H CH ₃ HH 3-F 1 (G ² -1-a) -4-CF ₃
N Cl OCH ₃ H CH ₃ HH 3-F 1 (G ² -1-a) -2,4-Cl ₂
N Cl OCH ₃ H CH ₃ HH 3-F 1 (G ² -1-a) -2-Cl ₄ -CF ₃
N Cl OCH ₃ H CH ₃ HH 3-F 1 (G ² -4-b) -6-Cl
CH Cl OCH ₃ H CH ₃ HH 3-F 1 (G ² -1-a) -4-CF ₃
CH Cl OCH ₃ H CH ₃ HH 3-F 1 (G ² -1-a) -2,4-Cl ₂
CH Cl OCH ₃ H CH ₃ HH 3-F 1 (G ² -1-a) -2-Cl ₄ -CF ₃
CH Cl OCH ₃ H CH ₃ HH 3-F 1 (G ² -4-b) -6-Cl
N Cl FFHHH 3-F 1 (G ² -1-a) -4-CF ₃
N Cl FFHHH 3-F 1 (G ² -1-a) -2,4-Cl ₂
N Cl FFHHH 3-F 1 (G ² -1-a) -2-Cl ₄ -CF ₃
N Cl FFHHH 3-F 1 (G ² -4-b) -6-Cl
CH Cl FFHHH 3-F 1 (G ² -1-a) -4-CF ₃
CH Cl FFHHH 3-F 1 (G ² -1-a) -2,4-Cl ₂
CH Cl FFHHH 3-F 1 (G ² -1-a) -2-Cl ₄ -CF ₃
CH Cl FFHHH 3-F 1 (G ² -4-b) -6-Cl
N Cl FF CH ₃ HH 3-F 1 (G ² -1-a) -4-CF ₃
N Cl FF CH ₃ HH 3-F 1 (G ² -1-a) -2,4-Cl ₂
N Cl FF CH ₃ HH 3-F 1 (G ² -1-a) -2-Cl ₄ -CF ₃
N Cl FF CH ₃ HH 3-F 1 (G ² -4-b) -6-Cl
CH Cl FF CH ₃ HH 3-F 1 (G ² -1-a) -4-CF ₃
CH Cl FF CH ₃ HH 3-F 1 (G ² -1-a) -2,4-Cl ₂
CH Cl FF CH ₃ HH 3-F 1 (G ² -1-a) -2-Cl ₄ -CF ₃
CH Cl FF CH ₃ HH 3-F 1 (G ² -4-b) -6-Cl
N Cl HHHHH 2-Cl 1 (G ² -1-a) -4-CF ₃
N Cl HHHHH 2-Cl 1 (G ² -1-a) -2,4-Cl ₂
N Cl HHHHH 2-Cl 1 (G ² -1-a) -2-Cl ₄ -CF ₃
N Cl HHHHH 2-Cl 1 (G ² -4-b) -6-Cl
CH Cl HHHHH 2-Cl 1 (G ² -1-a) -4-CF ₃
CH Cl HHHHH 2-Cl 1 (G ² -1-a) -2,4-Cl ₂
CH Cl HHHHH 2-Cl 1 (G ² -1-a) -2-Cl ₄ -CF ₃
CH Cl HHHHH 2-Cl 1 (G ² -4-b) -6-Cl
N Cl HH CH ₃ HH 2-Cl 1 (G ² -1-a) -4-CF ₃
N Cl HH CH ₃ HH 2-Cl 1 (G ² -1-a) -2,4-Cl ₂
N Cl HH CH ₃ HH 2-Cl 1 (G ² -1-a) -2-Cl ₄ -CF ₃
N Cl HH CH ₃ HH 2-Cl 1 (G ² -4-b) -6-Cl
CH Cl HH CH ₃ HH 2-Cl 1 (G ² -1-a) -4-CF ₃
CH Cl HH CH ₃ HH 2-Cl 1 (G ² -1-a) -2,4-Cl ₂
CH Cl HH CH ₃ HH 2-Cl 1 (G ² -1-a) -2-Cl ₄ -CF ₃
CH Cl HH CH ₃ HH 2-Cl 1 (G ² -4-b) -6-Cl
N Cl OCH ₃ H CH ₃ HH 2-Cl 1 (G ² -1-a) -4-CF ₃
N Cl OCH ₃ H CH ₃ HH 2-Cl 1 (G ² -1-a) -2,4-Cl ₂
N Cl OCH ₃ H CH ₃ HH 2-Cl 1 (G ² -1-a) -2-Cl ₄ -CF ₃
N Cl OCH ₃ H CH ₃ HH 2-Cl 1 (G ² -4-b) -6-Cl
CH Cl OCH ₃ H CH ₃ HH 2-Cl 1 (G ² -1-a) -4-CF ₃
CH Cl OCH ₃ H CH ₃ HH 2-Cl 1 (G ² -1-a) -2,4-Cl ₂
CH Cl OCH ₃ H CH ₃ HH 2-Cl 1 (G ² -1-a) -2-Cl ₄ -CF ₃
CH Cl OCH ₃ H CH ₃ HH 2-Cl 1 (G ² -4-b) -6-Cl
N Cl FFHHH 2-Cl 1 (G ² -1-a) -4-CF ₃
N Cl FFHHH 2-Cl 1 (G ² -1-a) -2,4-Cl ₂
N Cl FFHHH 2-Cl 1 (G ² -1-a) -2-Cl ₄ -CF ₃
N Cl FFHHH 2-Cl 1 (G ² -4-b) -6-Cl
CH Cl FFHHH 2-Cl 1 (G ² -1-a) -4-CF ₃
CH Cl FFHHH 2-Cl 1 (G ² -1-a) -2,4-Cl ₂
CH Cl FFHHH 2-Cl 1 (G ² -1-a) -2-Cl ₄ -CF ₃
CH Cl FFHHH 2-Cl 1 (G ² -4-b) -6-Cl
N Cl FF CH ₃ HH 2-Cl 1 (G ² -1-a) -4-CF ₃
N Cl FF CH ₃ HH 2-Cl 1 (G ² -1-a) -2,4-Cl ₂
N Cl FF CH ₃ HH 2-Cl 1 (G ² -1-a) -2-Cl ₄ -CF ₃
N Cl FF CH ₃ HH 2-Cl 1 (G ² -4-b) -6-Cl
CH Cl FF CH ₃ HH 2-Cl 1 (G ² -1-a) -4-CF ₃
CH Cl FF CH ₃ HH 2-Cl 1 (G ² -1-a) -2,4-Cl ₂
CH Cl FF CH ₃ HH 2-Cl 1 (G ² -1-a) -2-Cl ₄ -CF ₃
CH Cl FF CH ₃ HH 2-Cl 1 (G ² -4-b) -6-Cl
N Cl HHHHH 3-Cl 1 (G ² -1-a) -4-CF ₃
N Cl HHHHH 3-Cl 1 (G ² -1-a) -2,4-Cl ₂
N Cl HHHHH 3-Cl 1 (G ² -1-a) -2-Cl ₄ -CF ₃
N Cl HHHHH 3-Cl 1 (G ² -4-b) -6-Cl
CH Cl HHHHH 3-Cl 1 (G ² -1-a) -4-CF ₃
CH Cl HHHHH 3-Cl 1 (G ² -1-a) -2,4-Cl ₂
CH Cl HHHHH 3-Cl 1 (G ² -1-a) -2-Cl ₄ -CF ₃
CH Cl HHHHH 3-Cl 1 (G ² -4-b) -6-Cl
N Cl HH CH ₃ HH 3-Cl 1 (G ² -1-a) -4-CF ₃
N Cl HH CH ₃ HH 3-Cl 1 (G ² -1-a) -2,4-Cl ₂
N Cl HH CH ₃ HH 3-Cl 1 (G ² -1-a) -2-Cl ₄ -CF ₃
N Cl HH CH ₃ HH 3-Cl 1 (G ² -4-b) -6-Cl
CH Cl HH CH ₃ HH 3-Cl 1 (G ² -1-a) -4-CF ₃
CH Cl HH CH ₃ HH 3-Cl 1 (G ² -1-a) -2,4-Cl ₂
CH Cl HH CH ₃ HH 3-Cl 1 (G ² -1-a) -2-Cl ₄ -CF ₃
CH Cl HH CH ₃ HH 3-Cl 1 (G ² -4-b) -6-Cl
N Cl OCH ₃ H CH ₃ HH 3-Cl 1 (G ² -1-a) -4-CF ₃
N Cl OCH ₃ H CH ₃ HH 3-Cl 1 (G ² -1-a) -2,4-Cl ₂
N Cl OCH ₃ H CH ₃ HH 3-Cl 1 (G ² -1-a) -2-Cl ₄ -CF ₃
N Cl OCH ₃ H CH ₃ HH 3-Cl 1 (G ² -4-b) -6-Cl
CH Cl OCH ₃ H CH ₃ HH 3-Cl 1 (G ² -1-a) -4-CF ₃
CH Cl OCH ₃ H CH ₃ HH 3-Cl 1 (G ² -1-a) -2,4-Cl ₂
CH Cl OCH ₃ H CH ₃ HH 3-Cl 1 (G ² -1-a) -2-Cl ₄ -CF ₃
CH Cl OCH ₃ H CH ₃ HH 3-Cl 1 (G ² -4-b) -6-Cl
N Cl FFHHH 3-Cl 1 (G ² -1-a) -4-CF ₃
N Cl FFHHH 3-Cl 1 (G ² -1-a) -2,4-Cl ₂
N Cl FFHHH 3-Cl 1 (G ² -1-a) -2-Cl ₄ -CF ₃
N Cl FFHHH 3-Cl 1 (G ² -4-b) -6-Cl
CH Cl FFHHH 3-Cl 1 (G ² -1-a) -4-CF ₃
CH Cl FFHHH 3-Cl 1 (G ² -1-a) -2,4-Cl ₂
CH Cl FFHHH 3-Cl 1 (G ² -1-a) -2-Cl ₄ -CF ₃
CH Cl FFHHH 3-Cl 1 (G ² -4-b) -6-Cl
N Cl FF CH ₃ HH 3-Cl 1 (G ² -1-a) -4-CF ₃
N Cl FF CH ₃ HH 3-Cl 1 (G ² -1-a) -2,4-Cl ₂
N Cl FF CH ₃ HH 3-Cl 1 (G ² -1-a) -2-Cl ₄ -CF ₃
N Cl FF CH ₃ HH 3-Cl 1 (G ² -4-b) -6-Cl
CH Cl FF CH ₃ HH 3-Cl 1 (G ² -1-a) -4-CF ₃
CH Cl FF CH ₃ HH 3-Cl 1 (G ² -1-a) -2,4-Cl ₂
CH Cl FF CH ₃ HH 3-Cl 1 (G ² -1-a) -2-Cl ₄ -CF ₃
CH Cl FF CH ₃ HH 3-Cl 1 (G ² -4-b) -6-Cl
N Cl HHHHH 3,5-F2 2 (G ² -1-a) -4-CF ₃
N Cl HHHHH 3,5-F2 2 (G ² -1-a) -2,4-Cl ₂
N Cl HHHHH 3,5-F2 2 (G ² -1-a) -2-Cl ₄ -CF ₃
N Cl HHHHH 3,5-F2 2 (G ² -4-b) -6-Cl
CH Cl HHHHH 3,5-F2 2 (G ² -1-a) -4-CF ₃
CH Cl HHHHH 3,5-F2 2 (G ² -1-a) -2,4-Cl ₂
CH Cl HHHHH 3,5-F2 2 (G ² -1-a) -2-Cl ₄ -CF ₃
CH Cl HHHHH 3,5-F2 2 (G ² -4-b) -6-Cl
N Cl HH CH ₃ HH 3,5-F2 2 (G ² -1-a) -4-CF ₃
N Cl HH CH ₃ HH 3,5-F2 2 (G ² -1-a) -2,4-Cl ₂
N Cl HH CH ₃ HH 3,5-F2 2 (G ² -1-a) -2-Cl ₄ -CF ₃
N Cl HH CH ₃ HH 3,5-F2 2 (G ² -4-b) -6-Cl
CH Cl HH CH ₃ HH 3,5-F2 2 (G ² -1-a) -4-CF ₃
CH Cl HH CH ₃ HH 3,5-F2 2 (G ² -1-a) -2,4-Cl ₂
CH Cl HH CH ₃ HH 3,5-F2 2 (G ² -1-a) -2-Cl ₄ -CF ₃
CH Cl HH CH ₃ HH 3,5-F2 2 (G ² -4-b) -6-Cl
N Cl OCH ₃ H CH ₃ HH 3,5-F2 2 (G ² -1-a) -4-CF ₃
N Cl OCH ₃ H CH ₃ HH 3,5-F2 2 (G ² -1-a) -2,4-Cl ₂
N Cl OCH ₃ H CH ₃ HH 3,5-F2 2 (G ² -1-a) -2-Cl ₄ -CF ₃
N Cl OCH ₃ H CH ₃ HH 3,5-F2 2 (G ² -4-b) -6-Cl
CH Cl OCH ₃ H CH ₃ HH 3,5-F2 2 (G ² -1-a) -4-CF ₃
CH Cl OCH ₃ H CH ₃ HH 3,5-F2 2 (G ² -1-a) -2,4-Cl ₂
CH Cl OCH ₃ H CH ₃ HH 3,5-F2 2 (G ² -1-a) -2-Cl ₄ -CF ₃
CH Cl OCH ₃ H CH ₃ HH 3,5-F2 2 (G ² -4-b) -6-Cl
N Cl FFHHH 3,5-F2 2 (G ² -1-a) -4-CF ₃
N Cl FFHHH 3,5-F2 2 (G ² -1-a) -2,4-Cl ₂
N Cl FFHHH 3,5-F2 2 (G ² -1-a) -2-Cl ₄ -CF ₃
N Cl FFHHH 3,5-F2 2 (G ² -4-b) -6-Cl
CH Cl FFHHH 3,5-F2 2 (G ² -1-a) -4-CF ₃
CH Cl FFHHH 3,5-F2 2 (G ² -1-a) -2,4-Cl ₂
CH Cl FFHHH 3,5-F2 2 (G ² -1-a) -2-Cl ₄ -CF ₃
CH Cl FFHHH 3,5-F2 2 (G ² -4-b) -6-Cl
N Cl FF CH ₃ HH 3,5-F2 2 (G ² -1-a) -4-CF ₃
N Cl FF CH ₃ HH 3,5-F2 2 (G ² -1-a) -2,4-Cl ₂
N Cl FF CH ₃ HH 3,5-F2 2 (G ² -1-a) -2-Cl ₄ -CF ₃
N Cl FF CH ₃ HH 3,5-F2 2 (G ² -4-b) -6-Cl
CH Cl FF CH ₃ HH 3,5-F2 2 (G ² -1-a) -4-CF ₃
CH Cl FF CH ₃ HH 3,5-F2 2 (G ² -1-a) -2,4-Cl ₂
CH Cl FF CH ₃ HH 3,5-F2 2 (G ² -1-a) -2-Cl ₄ -CF ₃
CH Cl FF CH ₃ HH 3,5-F2 2 (G ² -4-b) -6-Cl
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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. , Shirasu, Kira, Talc, Bentonite, Activated clay, Acid clay, Pumice, Attapulgite, Zeolite and diatomite 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 promoting substance, a protective agent, an antioxidant, a light-shielding agent, a thickening substance, etc. 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-butylyl 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]
Compounds 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. 5-001 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.1-002 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. 3-003 4 parts DBE 36 parts (mixture of dimethyl adipate, dimethyl glutarate, dimethyl succinate: trade name of 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 company name)
The above is uniformly mixed to obtain an emulsion.

[Formulation Example 4] Milk Compound of the present invention No.1-001 4 parts DBE 11 parts (mixture of dimethyl adipate, dimethyl glutarate, dimethyl succinate: trade name of 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 company name)
Propylene glycol 10 parts Water 20 parts or more are mixed uniformly to make an emulsion.

[Formulation Example 5] Suspension Agent Compound No. 1-008 25 parts Agrisol S-710 10 parts (Nonionic surfactant: Kao Corporation trade name)
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. 7-003 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.

[Composition Example 8] Powder Compound of the present invention No.1-004 3 parts Carplex # 80D 0.5 part (Synthetic hydrous silicic acid: Shionogi & 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. 6-011 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. 3-001 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.1-003 2 parts dimethyl sulfoxide 10 parts 2-propanol 35 parts acetone 53 parts [Formulation Example 12] transdermal Solution for administration The present compound No. 2 001 5 parts Hexylene glycol 50 parts Isopropanol 45 parts [Formulation example 13] Solution for transdermal administration Compound No. 3-001 5 parts Propylene glycol monomethyl ether 50 parts Dipropylene glycol 45 parts [Formulation example 14] Transdermal administration (Drip) Liquid Compound of the Invention Compound No. 7-003 2 parts Light Liquid Paraffin 98 parts [Formulation Example 15] Solution for Transdermal Administration (Drip) Compound No. 6-011 2 parts 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,
Pyridachlometyl,
C: Respiratory inhibitor diflumetorim,
Benodanil, benzovindiflupyr, bixafen, boscalid, carboxin, fenfuram, fluindapyr, fluopyram, flutolanil, flutolanil Xapyroxad (fluxapyroxad), furametpyr, inpyrifluxam, isofetamid, isoflucypram, isoplucam, isoprazam, mepronil, oxycarboxin, pen (Penflufen), penthiopyrad, pydiflumetofen, pyraziflumid, sedaxane, thifluzamide, F9650 (study name),
Azoxystrobin, coumoxystrobin, dimoxystrobin, enestrobin, enoxastrobin, famoxadone, fenamidone, phenaminestrobin ( fenaminstrobin, flufenoxystrobin, fluoxastrobin, kresoxim-methyl, mandestrobin, metinominostrobin, methyltetraprole, oryastrobine (Orysastrobin), picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, pyribencarb-methyl, pyrinostrobin Bin (pyriminostrobin), triclopyricab, trifloxystrobin,
Amisulbrom, cyazofamid,
Dinocap, fluazinam, meptyldinocap,
Fentin, tributyltin oxide,
Silthiofam,
Ametoctradin,
Fenpicoxamid, florylpicoxamid,
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 and cell membrane synthesis 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, ipfentrifluconazole, mefentrifluconazole, metcona zole), microbutanil, nuarimol, oxpoconazole fumarate, pefurazoate, penconazole, prochloraz, propiconazole, prothioconazole (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,
Tolprocarb,
P: Plant resistance inducer acibenzolar-S-methyl,
Diclobentiazox, 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 UN; mechanism of action unknown and other drugs aminopyrifen, cyflufenamid, cymoxanil, diclomezine, dipymetitrone, dodine, ferimzone, fluopimide fluopimomide, flusulfamide, flutianil, fosetyl-aluminium, ipflufenoquin, metrafenone, oxathiapiprolin, oxathiapiprolin, picarbutrazox , Pyrapropoyne, pyriofenone, quinofumelin, tebufloquin, triazoxide, potassium hydrogen carbonate, sodium hydrogen carbonate (sodiu m hydrogen carbonate), shiitake mycelium extract, shiitake fruiting body extract and NF-180 (test name).

Insecticides and acaricides:
A: Acetylcholinesterase (AChE) inhibitor Alanicarb, aldicarb, bendiocarb, benfuracarb, butofcarboxim, 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,
B: GABAergic chloride channel antagonist endosulfan, alpha-endosulfan,
Ethiprole, fipronil, flufiprole, pyriprole,
Afoxolaner, fluralaner, fluxametamide, lotilaner, sarolaner, tigolaner,
C: sodium channel modulators acrinathrin, allethrin, benfluthrin, bifenthrin, kappa-bifenthrin, bioallethrin, bioresmethrin, chloropralethrin ), Cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, cypermethrin ), Alpha-cypermethrin (alpha-cypermethrin), beta-cypermethrin (beta-cypermethrin), zeta-cypermethrin (zeta-cypermethrin), cyphenothrin (cyphenothrin), deltamethrin (deltamethrin) Empenthrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucytrinate, flumethrin, fluvalinate, Tau-fluvalinate, halfenprox, heptafluthrin, hemiprothrin, meperfluthrin, metofluthrin, epsilon-metofluthrin, epsilon-metofluthrin Thrin (momfluorothrin), epsilon-momfluorothrin, permethrin, phenothrin, pyrethrin, resmethrin, silafluophene (Silafluofen), tefluthrin, kappa-tefluthrin, tetramethrin, dT-80-phthalthrin (d-tetramethrin), tetramethylfluthrin, tralomethrin, trans Flutrin, transfluthrin,
Methoxychlor,
D: Nicotinic acetylcholine receptor (nAChR) agonists acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, thiamethoxam
Sulfoxaflor,
Flupyradifurone,
Fluprimin,
Dicloromezotiaz, triflumezopyrim,
E; nicotinic acetylcholine receptor (nAChR) allosteric modulators spinetoram, spinosad,
F: glutamatergic chloride channel activator abamectin, emamectin-benzoate, lepimectin, milbemectin,
G; juvenile hormone analog mesoprene,
Phenoxycarb,
Pyriproxyfen,
H; Hemiptera selective feeding inhibitor pymetrozine,
Flonicamid,
I; mite growth inhibitor clofentezine, hexythiazox,
Etoxazole,
J: Microbial-derived insect midgut mesentery bacillus thuringiensis (bacillus thuringiensis, subsp.israelensis, subsp.aizawai, subsp.kurstaki, subsp.tenebrionis, etc.)
K; mitochondrial ATP synthase inhibitor diafenthiuron,
Azocyclotin, fenbutatin oxide,
Propargite,
L: oxidative phosphorylation uncoupler, chlorfenapyr,
M; nicotinic acetylcholine receptor (nAChR) channel blocker bensultap, cartap, thiocyclam,
N: chitin biosynthesis inhibitor (type 0)
Bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron ), Nobifluuron, teflubenzuron, triflumuron,
O: Chitin biosynthesis inhibitor (type 1)
Buprofezin,
P: molting inhibitor (fly insect)
Cyromazine,
Q: molting hormone (ecdysone) receptor agonist chromafenozide, halofenozide, methoxyfenozide, tebufenozide, tebufenozide,
R; octopamine receptor agonist amitraz,
S: Mitochondrial electron transport system complex III inhibitor hydramethylnon,
Acequinocyl,
Fluacrypyrim,
T: Mitochondrial electron transport complex I inhibitor fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad, tolfenpyrad,
Rotenone,
U; voltage-gated sodium channel blocker indoxacarb (indoxacarb), indoxacarb-MP (indoxacarb-MP),
Metaflumizone,
V: Acetyl CoA carboxylase inhibitor spirodiclofen, spiromesifen, spiropidion, spirotetramat,
W: Mitochondrial electron transport system complex II inhibitor cyenopyrafen, cyflumetofen,
Piflubumide,
X: Ryanodine receptor modulator chlorantraniliprole, cyantraniliprole, cyclaniliprole, cyhalodiamide, flubendiamide, tetraniliprole,
UN: unknown mechanism of action and other drugs azadirachtin, benzoximate, bifenazate, bromopropylate, dicohol, pyridalyl, pyrifluquinazon,
Acynonapyr, afidopyropen, benzpyrimoxan, broflanilide, flometoquin, fluhexafon, oxazosulfyl, ticazopyrazol and tyclopyrazoflor (Exam name).

Nematicides:
A: Acetylcholinesterase (AChE) inhibitor Oxamyl,
Cadusafos, dichlofenthion, ethoprophos, fenamiphos, fosthiazate, fosthietan, imcyafos, isamifos, isazofos, isazofos
And UN; unknown mechanism of action and other drugs fluazaindolizine, fluensulfone, methyl bromide, methyl isothiocyanate, sodium azide and thioxazaphene (Tioxazafen) etc.

Anthelmintic:
A: Acetylcholinesterase (AChE) inhibitor propoxur,
Coumaphos, propetamphos,
B; nicotinic acetylcholine receptor (nAChR) antagonist monepantel,
C: GABAergic chloride channel agonist piperazine adipate, piperazine citrate, piperazine phosphate,
D: glutamatergic chloride channel activator doramectin, eprinomectin, ivermectin, milbemycin oxime, moxidectin, selamectin,
E; Latrophylline receptor agonist emodepside,
F: Depolarizing neuromuscular blocking agent Morantel tartrate, oxantel pamoate, oxantel tartrate, pyrantel pamoate,
G: oxidative phosphorylation uncoupler bromofenofos, closantel,
H; a reduction of fumaric acid and an oxidation inhibitor of succinic acid, levamisole,
I: Nucleic acid biosynthesis inhibitor sulfadimethoxine, sulfadoxine, sulfamerazine, sulfamonomethoxine, sulfamoildapsone,
Pyrimethamine,
Furazolidone,
Metronidazole, tinidazole,
J: Mitotic and cell division inhibitors albendazole, cambendazole, febantel, fenbendazole, flubendazole, mebendazole, oxfendazolee ), Oxibendazole, parbendazole, thiabendazole, triclabendazole,
And UN; mechanism of action unknown and other drugs bithionol, carnidazole, thiacetalsamide, chloroquine, clazuril, clorsulon, cimiazol, dichlorophen ), Diethylcarbamazine, diminazene, disophenol, dithiazanine iodide, glycalpyramide, imidocarb, mefloquine, melarsomine dihydrochloride ( melarsamine hydrochloride, metyridine, nicarbazin, niclosamide, nitroscanate, nitroxynil, omphalotin, oxyclozanide nide, pamaquine, ponazuril, praziquantel, primaquine, santonin, toltrazuril, tribromsalan, PNU-97333 (paraherquamide A) and PNU- 141962 (2-deoxyparaherquamide) and the like.

Antifungal agents:
A: Respiratory inhibitor atovaguone,
B: Sterol biosynthesis inhibitor climbazole, clotrimazole, econazole nitrate, itraconazole, ketoconazole, miconazole nitrate, sulconazole nitrate,
Tolnaftate,
C: oxidative phosphorylation uncoupler pyrrolnitrin,
D: Nucleic acid biosynthesis inhibitor flucytosine,
E: Cell membrane disrupting agent amphotericin B (amphotericin B), tricomycin (trichomycin),
F: Mitosis and cell division inhibitor, griseofulvin,
And UN; mechanism of action unknown and other drugs acriflavine, etc.

Antibacterial agent:
A: DNA / RNA synthesis inhibitor octhilinone,
B: DNA topoisomerase type II inhibitor miloxacin, oxolinic acid,
Danofloxacin, difloxacin, enrofloxacin, lomefloxacin, marbofloxacin, nadifloxacin, norfloxacin, ofloxacin, orloxacin (Orbifloxacin),
C: dihydrofolate reductase inhibitor olmethoprim (ormethoprim), trimethoprim (trimethoprim),
D: protein synthesis inhibitor chloramphenicol (chloramphenicol), florfenicol (florfenicol), thiamphenicol (thiamphenicol),
Erythromycin,
Azithromycin, tulathromycin,
Josamycin, midecamycin, mirosamycin, tilmicosin phosphate, acetylisovaleryltylosin acetate, tylosin phosphate,
Clindamycin hydrochloride, lincomycin,
Tiamulin fumarate, valnemulin,
Chlortetracycline, doxycycline hydrochloride, minocycline hydrochloride, oxytetracycline,
Amikacin, arbekacin, gentamicin, micronomicin,
Streptomycin,
E: Cell wall synthesis inhibitor vancomycin,
Fosfomycin (fosfomycyn),
Aminopenicillin, amoxicillin, ampicillin, benzylpenicillin, penicillin, piperacillin,
Cefaclor, cefalexin, cefalothin, cefapirin, cefazolin, cefdinir, cefdinir, cefixime, cefoperazone, cefquin, cefquin, cefquinome Ceftiofur,
Cefmetazole,
Flomoxef, latamoxef,
Aztreonam,
F; β-lactamase inhibitor clavulanic acid, sulbactam,
G: Cell membrane disrupting agent, colistin,
H: Nitrification inhibitor nitrapyrin,
And UN; unknown mechanism of action and other drugs: bethoxazin, bronopol, dinitrmide, calcined shell calcium (calcium oxide), Talalomyces spp., Trichoderma spp.

  Hereinafter, the present invention will be described in more detail by specifically describing the 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- [4- [3-chloro-5- (trifluoromethyl) pyridin-2-yloxy] phenylethynyl] pyridin-2-yl] -2,2-difluoroethyl] -2- (Trifluoromethyl) benzamide (the present compound No.1-001)
Step 1: Preparation of 3-chloro-2- (4-iodophenoxy) -5- (trifluoromethyl) pyridine 1.08 g of 2,3-dichloro-5- (trifluoromethyl) pyridine N, N-dimethylformamide To the 5 ml solution, 2.07 g of potassium carbonate and 1.10 g of 4-iodophenol were added and stirred at room temperature for 12 hours. After completion of the reaction, 20 ml of water was added and extracted with ethyl acetate (20 ml). The organic layer was washed with water (10 ml × 2), dehydrated and dried in the order of saturated brine and then sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography eluting with ethyl acetate-hexane (gradient from 0:10 to 1: 9) to obtain 1.93 g of the desired product as a colorless oil.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.26 (brs, 1H), 7.98 (d, J = 2.4Hz, 1H), 7.70-7.80 (m, 2H), 6.90-7.00 (m, 2H ).

Step 2: Preparation of 3-chloro-5- (trifluoromethyl) -2- [4- (trimethylsilylethynyl) phenoxy] pyridine 3-chloro-2- (4-iodophenoxy) -5- (trifluoromethyl) pyridine To 1.93 g of N, N-dimethylformamide 5 ml solution, 1.96 g of triethylamine, 38 mg of copper (I) iodide, 170 mg of dichlorobis (triphenylphosphine) palladium (II), and 616 mg of trimethylsilylacetylene were sequentially added. Stir at room temperature for 12 hours. After completion of the reaction, 5 ml of ethyl acetate and 15 ml of saturated aqueous ammonium chloride solution were added, and the mixture was extracted with ethyl acetate (15 ml × 1). The organic layer was washed with water (20 ml × 1), dehydrated and dried in the order of saturated brine and sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography eluting with ethyl acetate-hexane (0:10 to 1: 9 gradient) to obtain 1.30 g of the desired product as a colorless oil.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.20-8.25 (m, 1H), 7.97 (d, J = 2.4Hz, 1H), 7.50-7.5 (m, 2H), 7.05-7.15 (m , 2H), 0.26 (s, 9H).

Step 3; N- [2- [3-Chloro-5- [4- [3-chloro-5- (trifluoromethyl) pyridin-2-yloxy] phenylethynyl] pyridin-2-yl] -2,2- Preparation of difluoroethyl] carbamic acid-tert-butyl N- [2- [5-bromo-3-chloropyridin-2-yl] -2,2-difluoroethyl] carbamic acid-tert-butyl 760 mg of N, N- To a 5 ml solution of dimethylformamide, 621 mg of triethylamine, 117 mg of copper (I) iodide, 144 mg of dichlorobis (triphenylphosphine) palladium (II), 3-chloro-5- (trifluoromethyl) -2- [4- (trimethylsilylethynyl) Phenoxy] pyridine 832 mg and tetra-n-butylammonium fluoride 1.0 M tetrahydrofuran Successively added a solution 2.3 ml, under a nitrogen atmosphere and stirred 2.5 hours at 70 ° C.. After completion of the reaction, 5 ml of ethyl acetate and 5 ml of water were added, followed by extraction with ethyl acetate (10 ml × 1). The organic layer was washed with 10 ml of an aqueous ammonia solution, dehydrated and dried with saturated brine and then 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 (0:10 to 3: 7 gradient) to obtain 844 mg of the desired product as a brown dendritic substance.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.58 (d, J = 1.8Hz, 1H), 8.25-8.30 (m, 1H), 8.00 (d, J = 2.1Hz, 1H), 7.92 ( d, J = 1.8Hz, 1H), 7.60-7.65 (m, 2H), 7.20-7.25 (m, 2H), 5.10-5.15 (m, 1H), 4.10 (td, J = 12.0, 6.3Hz, 2H) , 1.41 (s, 9H).

Step 4; of 2- [3-Chloro-5- [4- [3-chloro-5- (trifluoromethyl) pyridin-2-yloxy] phenylethynyl] pyridin-2-yl] -2,2-difluoroethylamine Preparation N- [2- [3-Chloro-5- [4- [3-chloro-5- (trifluoromethyl) pyridin-2-yloxy] phenylethynyl] pyridin-2-yl] -2,2-difluoroethyl 2 ml of trifluoroacetic acid was added to 6 ml of a dichloromethane solution of 800 mg of tert-butyl carbamate with stirring under ice cooling, and the mixture was stirred at 0 ° C. for 3 hours. After completion of the reaction, 10 ml of ethyl acetate and 10 ml of saturated aqueous sodium carbonate solution were added, and the mixture was extracted with ethyl acetate (10 ml × 2). The organic layers were combined, washed with a saturated aqueous sodium hydrogen carbonate solution, 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 660 mg of the crude target product as brown. Obtained as a dendritic material. This was directly used in the next step without further purification.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.61 (d, J = 1.8Hz, 1H), 8.25-8.30 (m, 1H), 8.01 (d, J = 2.4Hz, 1H), 7.93 ( d, J = 1.8Hz, 1H), 7.60-7.65 (m, 2H), 7.20-7.25 (m, 2H), 3.53 (t, J = 14.1Hz, 2H), 1.56 (br-s, 1H).

Step 5; N- [2- [3-Chloro-5- [4- [3-chloro-5- (trifluoromethyl) pyridin-2-yloxy] phenylethynyl] pyridin-2-yl] -2,2- Preparation of difluoroethyl] -2- (trifluoromethyl) benzamide 2- [3-Chloro-5- [4- [3-chloro-5- (trifluoromethyl) pyridin-2-yloxy] phenylethynyl] pyridine-2 -Yl] -2,2-difluoroethylamine In a solution of 154 mg of N, N-dimethylformamide in 2 ml, 72 mg of 2- (trifluoromethyl) benzoic acid, 96 mg of triethylamine, 5 mg of 4- (N, N-dimethylamino) pyridine and O -(Benzotriazol-1-yl) -N, N, N ′, N′-tetramethyluronium tetrafluoroborate 121 mg It was added, and stirred for 1 hour at room temperature. After completion of the reaction, 3 ml of water was added and extracted with ethyl acetate (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 chromatography eluting with ethyl acetate-hexane (1: 9 to 3: 7 gradient) to obtain 156 mg of the desired product as a brown solid.
Melting point 130-132 ° C
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.56 (d, J = 1.8Hz, 1H), 8.25-8.30 (m, 1H), 8.01 (d, J = 2.4Hz, 1H), 7.96 ( d, J = 1.8Hz, 1H), 7.50-7.70 (m, 6H), 7.20-7.25 (m, 2H), 6.49 (t, J = 6.0Hz, 1H), 4.47 (td, J = 13.2, 6.0Hz , 2H).

Synthesis example 2
N- [2- [2-Chloro-4- [4- [3-chloro-5- (trifluoromethyl) pyridin-2-yloxy] phenylethynyl] phenyl] -2,2-difluoro-1-methylethyl] -2- (Trifluoromethyl) nicotinamide (the present compound No. 5-001)
Step 1: Preparation of ethyl 2- (4-bromo-2-chlorophenyl) -2,2-difluoroacetate 4.40 g of copper was suspended in 20 ml of dimethyl sulfoxide, and 4-bromo-2-chloro-1-iodobenzene 3 was suspended. 0.2 g and 3.25 g of ethyl bromodifluoroacetate were added, and the mixture was stirred at 60 ° C. for 2 hours and then at room temperature for 12 hours under a nitrogen atmosphere. After completion of the reaction, 30 ml of a saturated aqueous ammonium chloride solution was added, and the precipitate was filtered through celite. The filtrate was extracted with diethyl ether (20 ml × 1), and the organic layer was dehydrated and dried in the order of saturated brine and then sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography eluting with ethyl acetate-hexane (0:10 to 2: 8 gradient) to obtain 2.40 g of the desired product as a brown dendritic material.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 7.45-7.60 (m, 3H), 4.25-4.40 (m, 2H) 1.20-1.35 (m, 3H).

Step 2; Preparation of 2- (4-bromo-3-chlorophenyl) -2,2-difluoroacetamide Ethyl 2- (4-bromo-3-chlorophenyl) -2,2-difluoro in 20 ml of 4 mass% ammonia-methanol solution 2.40 g of acetate was added and stirred at room temperature for 12 hours. After completion of the reaction, the solvent was distilled off under reduced pressure to obtain 2.10 g of the desired product as a white solid. This was directly used in the next step without further purification.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ7.55-7.65 (m, 2H), 7.45-7.55 (m, 1H), 6.51 (br-s, 1H), 6.14 (br-s, 1H) .

Step 3; Preparation of 2- (4-bromo-3-chlorophenyl) -2,2-difluoroacetonitrile 2- (4-Bromo-2-chlorophenyl) -2,2-difluoroacetamide 3.80 g of tetrahydrofuran in 30 ml solution 4.77 g of pyridine was added, and 5.63 g of trifluoroacetic anhydride was added dropwise with stirring under ice cooling. After completion of the addition, the mixture was stirred at the same temperature for 1 hour. After completion of the reaction, 20 ml of water was added and extracted with ethyl acetate (20 ml × 1). The organic layer was washed with water (20 ml × 1) and saturated aqueous sodium hydrogen carbonate solution (20 ml × 1), then dehydrated and dried in the order of saturated brine and then sodium sulfate, and then the solvent was distilled off under reduced pressure. The target product (3.20 g) was obtained as a brown dendritic material.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ7.65-7.80 (m, 1H), 7.50-7.60 (m, 2H).

Step 3; Preparation of 2- (4-bromo-2-chlorophenyl) -2,2-difluoro-1-methylethylamine 2- (4-bromo-2-chlorophenyl) -2,2-difluoroacetonitrile 1.80 g of diethyl To an ether 10 ml solution, 5 ml of a 35 mass% diethyl ether solution of methylmagnesium bromide was added dropwise with stirring under ice cooling. After completion of the addition, the mixture was stirred at the same temperature for 30 minutes. After completion of the reaction, 10 ml of methanol was added dropwise with stirring under ice cooling, and the mixture was stirred at the same temperature for 30 minutes. Then, 1.10 g of sodium borohydride was added in three portions and stirred at room temperature for 5 hours. After completion of the reaction, 20 ml of saturated aqueous ammonium chloride solution was added, and the mixture was extracted with ethyl acetate (20 ml × 1). The organic layer was dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 1.50 g of a crude desired product as a brown dendritic substance. This was directly used in the next step without further purification.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ7.55-7.65 (m, 1H), 7.35-7.50 (m, 2H), 3.55-3.85 (m, 1H), 1.15-1.40 (m, 2H) , 1.00-1.15 (m, 3H).

Step 4: Preparation of N- [2- (4-bromo-2-chlorophenyl) -2,2-difluoro-1-methylethyl] carbamic acid-tert-butyl 2- (4-bromo-2-chlorophenyl) -2 , 2-Difluoro-1-methylethylamine 1.60 g of triethylamine and 1.30 g of di-tert-butyl dicarbonate were added to a solution of 1.50 g of dichloromethane in 5 ml of dichloromethane and stirred at room temperature for 16 hours. After completion of the reaction, 10 ml of water was added and extracted with ethyl acetate (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 chromatography eluting with ethyl acetate-hexane (0: 10-25: 75) to obtain 1.15 g of the desired product as a yellow dendritic product.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ7.55-7.65 (m, 1H), 7.30-7.50 (m, 2H), 4.55-4.80 (m, 2H), 1.15-1.35 (m, 12H) .

Step 5: N- [2- [2-Chloro-4- [4- [3-chloro-5- (trifluoromethyl) pyridin-2-yloxy] phenylethynyl] phenyl] -2,2-difluoro-1- Preparation of methylethyl] carbamic acid-tert-butyl N- [2- (4-bromo-2-chlorophenyl) -2,2-difluoro-1-methylethyl] carbamic acid-tert-butyl in a 5 ml tetrahydrofuran solution 3-Chloro-5- (trifluoromethyl) -2- [4- (trimethylsilylethynyl) phenoxy] pyridine 846 mg, triethylamine 695 mg, copper iodide (I) 65 mg, dichlorobis (triphenyl) prepared in Step 2 of Synthesis Example 1 Phosphine) palladium (II) 80 mg and tetra-n-butylammonium fluoride 1M tetrahydride The lofuran solution (2.3 ml) was added, and the mixture was stirred at 60 ° C. for 3 hours under a nitrogen atmosphere. After completion of the reaction, 20 ml of water was added and extracted with ethyl acetate (30 ml × 1). The organic layer was washed with 20 ml of a saturated aqueous ammonium chloride solution, dehydrated and dried in the order of saturated brine and then sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography eluting with ethyl acetate-hexane (0:10 to 2: 8 gradient) to obtain 890 mg of the desired product as a brown solid.
Melting point 44-46 ° C
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.28 (s, 1H), 8.00 (d, J = 2.1 Hz, 1H), 7.35-7.70 (m, 5H), 7.15-7.20 (m, 2H ), 4.70-4.90 (m, 1H), 4.63 (d, J = 10.5Hz, 1H) 1.29 (d, J = 6.3Hz, 3H).

Step 6: Preparation of 2- [2-chloro-4- [4- [3-chloro-5- (trifluoromethyl) pyridin-2-yloxy] phenylethynyl] phenyl-2,2-difluoro-1-methylethylamine To a solution of 890 mg of N- [2- (4-bromo-2-chlorophenyl) -2,2-difluoro-1-methylethyl] carbamic acid-tert-butyl in 6 ml of dichloromethane was added 3 ml of trifluoroacetic acid at room temperature. Stir for 3 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. To the residue was added 10 ml of saturated aqueous potassium carbonate solution, and the mixture was extracted into ethyl acetate (10 ml × 1). The organic layer was washed with water (5 ml × 1), dehydrated and dried in the order of saturated brine and then sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 625 mg of the crude desired product as a brown oil. This was directly used in the next step without further purification.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.25-8.30 (m, 1H), 8.00 (d, J = 2.4Hz, 1H), 7.50-7.65 (m, 4H), 7.45-7.50 (m , 2H), 7.15-7.20 (m, 2H), 3.70-3.95 (m, 1H), 1.05-1.15 (m3H).

Step 7; N- [2- [2-Chloro-4- [4- [3-chloro-5- (trifluoromethyl) pyridin-2-yloxy] phenylethynyl] phenyl] -2,2-difluoro-1- Preparation of methylethyl] -2- (trifluoromethyl) nicotinamide 2- [2-chloro-4- [4- [3-chloro-5- (trifluoromethyl) pyridin-2-yloxy] phenylethynyl] phenyl- To a solution of 104 mg of 2,2-difluoro-1-methylethylamine in 2 ml of N, N-dimethylformamide, 65 mg of triethylamine, 5 mg of 4- (N, N-dimethylamino) pyridine and O- (benzotriazol-1-yl) -N, N, N ′, N′-tetramethyluronium tetrafluoroborate 82 mg, 4- (N, N-dimethylamino) pyridine 3 m And it was added 2- (trifluoromethyl) 49 mg nicotinic acid, and stirred for 12 hours at room temperature. After completion of the reaction, 3 ml of water was added and extracted with ethyl acetate (5 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 chromatography eluting with ethyl acetate-hexane (0:10 to 2: 8 gradient) to obtain 77 mg of the objective product as a colorless dendritic substance.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.75-8.80 (m, 1H), 8.25-8.30 (m, 1H), 7.95-8.00 (m, 1H), 7.40-7.75 (m, 2H) 7.15-7.25 (m, 2H), 5.94 (d, J = 9.0Hz, 1H), 5.35-5.50 (m, 1H), 1.34 (d, J = 7.2Hz, 3H).

Synthesis example 3
N- [1-[[3-Chloro-5- [4- [3-chloro-5- (trifluoromethyl) pyridin-2-yloxy] phenylethynyl] pyridin-2-yl] methyl] cyclopropyl] -2 -(Trifluoromethyl) benzamide (the present compound No. 1-009)
Step 1; Preparation of 1-[(5-bromo-3-chloro-pyridin-2-yl) methyl] cyclopropanamine 2- (5-Bromo-3-chloropyridin-2-yl) acetonitrile 2.38 g of diethyl To 20 ml of ether solution, 3.21 g of titanium (IV) tetraisopropoxide was added. While stirring at 0 ° C., 6.9 ml of 3.0M diethyl ether solution of ethylmagnesium bromide was added dropwise and stirred at room temperature for 1 hour. did. Next, 2.92 g of boron trifluoride diethyl ether complex was added dropwise to the reaction mixture, and the mixture was stirred at the same temperature for 2 hours. After completion of the reaction, the reaction mixture was stirred with ice cooling, 15 ml of a 10% by mass aqueous sodium hydroxide solution and 15 ml of ethyl acetate were added, and the mixture was further stirred for 30 minutes. The deposited precipitate was filtered using Celite, and the obtained filtrate 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 2.50 g of the desired product. Was obtained as a brown dendrite. This was directly used in the next step without further purification.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.55 (d, J = 1.8Hz, 1H), 7.84 (d, J = 1.8Hz, 1H), 3.04 (s, 2H), 1.90-2.00 ( m, 2H), 0.60-0.65 (m, 4H).

Step 2; Preparation of N- [1-[(5-bromo-3-chloropyridin-2-yl) methyl] cyclopropyl] -2- (trifluoromethyl) benzamide 1-[(5-bromo-3-chloro -Pyridin-2-yl) methyl] cyclopropanamine 2.50 g and triethylamine 2.08 g in a dichloromethane 10 ml solution with ice-cooling and stirring, 2.04 g of 2- (trifluoromethyl) benzoyl chloride was added dropwise. And stirred at room temperature for 1 hour. After completion of the reaction, 5 ml of water was added to the reaction mixture and extracted with chloroform (5 ml × 2). 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 chromatography eluting with ethyl acetate-hexane (gradient 5: 95-30: 70) to obtain 584 mg of the objective product as a yellow solid.
Melting point 151-152 ° C
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 8.48 (d, J = 1.8Hz, 1H), 7.83 (d, J = 1.8Hz, 1H), 7.45-7.65 (m, 4H), 6.56 ( s, 1H), 3.28 (s, 2H), 0.90-1.10 (m, 4H).

Step 3; N- [1-[[3-Chloro-5- [4- [3-chloro-5- (trifluoromethyl) pyridin-2-yloxy] phenylethynyl] pyridin-2-yl] methyl] cyclopropyl Preparation of 2- (trifluoromethyl) benzamide N- [1-[(5-Bromo-3-chloropyridin-2-yl) methyl] cyclopropyl] -2- (trifluoromethyl) benzamide 159 mg of N, 163 mg of 3-chloro-5- (trifluoromethyl) -2- [4- (trimethylsilylethynyl) phenoxy] pyridine prepared in Step 2 of Synthesis Example 1 in 3 ml of N-dimethylformamide solution, 111 mg of triethylamine, copper iodide (I ) 14 mg, palladium acetate (II) 16 mg, 4,5-bis (diphenylphosphino) -9,9-dimethylxan Ten mg of Ten and 0.4 ml of a 1.0M tetrahydrofuran solution of tetra-n-butylammonium fluoride were sequentially added, and the mixture was stirred at 70 ° C. for 3 hours under a nitrogen atmosphere. After completion of the reaction, 5 ml of water was added and extracted with ethyl acetate (5 ml × 1, 10 ml × 1). The organic layers were combined and washed with 5 ml of a 10% by mass aqueous ammonia solution, 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 chromatography eluting with ethyl acetate-hexane (1: 9 to 3: 7 gradient) to obtain 107 mg of the objective compound as a brown solid.
Melting point 265-267 ° C
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.54 (d, J = 1.8Hz, 1H), 8.28 (dd, J = 2.4, 1.2Hz, 1H), 8.00 (d, J = 1.2Hz, 1H), 7.79 (d, J = 1.8Hz, 1H), 7.45-7.65 (m, 6H), 7.15-7.20 (m, 2H), 6.64 (s, 2H), 3.35 (s, 2H), 0.95-1.10 (m, 4H).

  This invention compound can be manufactured according to the said manufacturing method and an Example. Tables 3 to 14 show phenylacetylene-substituted amide compounds which are produced in the same manner as in Synthesis Example 1 to Synthesis Example 3, and Tables 15 and 16 show examples of production intermediates thereof. As shown, the phenylacetylene-substituted amide compounds and intermediates included in the present invention are not limited to these.

In the table, (G ² -1-a) -2-Cl-4-CF ₃ , (G ² -1-a) -2,4-Cl ₂ , (G ² -1-a) -4-CF ₃ and (G ² -4-b) -6-Cl represent the following structures respectively:

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

――――――――――――――――――――――――――――――――――――――――
No. R ¹ R ² R ³ R ⁴ AY ² G ² mp (℃)
――――――――――――――――――――――――――――――――――――――――
1-001 FFHHNH (G ² -1-a) -2-Cl-4-CF ₃ 119-121
1-002 HHHHNH (G ² -1-a) -2-Cl-4-CF ₃ 147-149
1-003 FF CH ₃ H CH H (G ² -1-a) -2-Cl-4-CF ₃ * 1
1-004 HHHHNH (G ² -1-a) -2,4-Cl ₂ 150-153
1-005 -CH ₂ CH ₂ -HHNH (G ² -1-a) -2-Cl-4-CF ₃ * 1
1-006 HH CH ₃ HNH (G ² -1-a) -2-Cl-4-CF ₃ * 1
1-007 FFHHNH (G ² -1-a) -2,4-Cl ₂ * 1
1-008 OCH ₃ H CH ₃ H CH H (G ² -1-a) -2-Cl-4-CF ₃ * 1
1-009 HH -CH ₂ CH ₂ -NH (G ² -1-a) -2-Cl-4-CF ₃ 265-267
1-010 HHHH CH H (G ² -1-a) -2-Cl-4-CF ₃ * 1
1-011 OCH ₃ HHH CH H (G ² -1-a) -2-Cl-4-CF ₃ 56-59
1-012 FFHHNH (G ² -4-b) -6-Cl 181-187
1-013 FFHHNF (G ² -1-a) -2-Cl-4-CF ₃ 136-138
1-014 FFHHNH (G ² -1-a) -4-CF ₃ 127-130
1-015 CH ₃ HHH CH H (G ² -1-a) -2-Cl-4-CF ₃ 136-139
――――――――――――――――――――――――――――――――――――――――
Table 4

――――――――――――――――――――――――――――――――――――――――
No. R ¹ R ² R ³ R ⁴ AY ² G ² mp (℃)
――――――――――――――――――――――――――――――――――――――――
2-001 HHHHNH (G ² -1-a) -2,4-Cl ₂ 146-149
2-002 -CH ₂ CH ₂ -HHNH (G ² -1-a) -2-Cl-4-CF ₃ * 1
2-003 HH CH ₃ HNH (G ² -1-a) -2-Cl-4-CF ₃ 131-132
――――――――――――――――――――――――――――――――――――――――
Table 5

――――――――――――――――――――――――――――――――――――――――
No. R ¹ R ² R ³ R ⁴ AY ² G ² mp (℃)
――――――――――――――――――――――――――――――――――――――――
3-001 FF CH ₃ H CH H (G ² -1-a) -2-Cl-4-CF ₃ * 1
3-002 HH CH ₃ HNH (G ² -1-a) -2,4-Cl ₂ 162-164
3-003 -CH ₂ CH ₂ -HHNH (G ² -1-a) -2-Cl-4-CF ₃ * 1
3-004 HH CH ₃ HNH (G ² -1-a) -2-Cl-4-CF ₃ 106-108
3-005 FFHHNH (G ² -1-a) -2,4-Cl ₂ 165-166
3-006 OCH ₃ H CH ₃ H CH H (G ² -1-a) -2-Cl-4-CF ₃ 142-144
3-007 HHHH CH H (G ² -1-a) -2-Cl-4-CF ₃ 141-144
3-008 OCH ₃ HHH CH H (G ² -1-a) -2-Cl-4-CF ₃ * 1
3-009 FFHHNF (G ² -1-a) -2-Cl-4-CF ₃ 164-166
3-010 FFHHNH (G ² -1-a) -2-Cl-4-CF ₃ 135-137
3-011 FFHHNH (G ² -1-a) -4-CF ₃ 152-154
――――――――――――――――――――――――――――――――――――――――
Table 6

――――――――――――――――――――――――――――――――――――――――
No. R ¹ R ² R ³ R ⁴ AY ² G ² mp (℃)
――――――――――――――――――――――――――――――――――――――――
4-001 OCH ₃ H CH ₃ H CH H (G ² -1-a) -2-Cl-4-CF ₃ * 1
――――――――――――――――――――――――――――――――――――――――
Table 7

――――――――――――――――――――――――――――――――――――――――
No. R ¹ R ² R ³ R ⁴ AY ² G ² mp (℃)
――――――――――――――――――――――――――――――――――――――――
5-001 FF CH ₃ H CH H (G ² -1-a) -2-Cl-4-CF ₃ * 1
5-002 HHHHNH (G ² -1-a) -2,4-Cl ₂ 171-174
5-003 FFHHNH (G ² -1-a) -2,4-Cl ₂ 169-173
――――――――――――――――――――――――――――――――――――――――
Table 8

――――――――――――――――――――――――――――――――――――――――
No. R ¹ R ² R ³ R ⁴ AY ² G ² mp (℃)
――――――――――――――――――――――――――――――――――――――――
6-001 HHHHNH (G ² -1-a) -2-Cl-4-CF ₃ 156-159
6-002 FF CH ₃ H CH H (G ² -1-a) -2-Cl-4-CF ₃ * 1
6-003 HHHHNH (G ² -1-a) -2,4-Cl ₂ 182-184
6-004 -CH ₂ CH ₂ -HHNH (G ² -1-a) -2-Cl-4-CF ₃ 170-173
6-005 HH CH ₃ HNH (G ² -1-a) -2-Cl-4-CF ₃ 167-170
6-006 FFHHNH (G ² -1-a) -2,4-Cl ₂ 116-118
6-007 OCH ₃ H CH ₃ H CH H (G ² -1-a) -2-Cl-4-CF ₃ * 1
6-008 OCH ₃ HHH CH H (G ² -1-a) -2-Cl-4-CF ₃ 159-162
6-009 FFHHNH (G ² -4-b) -6-Cl 186-190
6-010 FFHHNF (G ² -1-a) -2-Cl-4-CF ₃ 145-147
6-011 FFHHNH (G ² -1-a) -2-Cl-4-CF ₃ 131-133
6-012 FFHHNH (G ² -1-a) -4-CF ₃ 147-151
6-013 CH ₃ HHH CH H (G ² -1-a) -2-Cl-4-CF ₃ 169-172
――――――――――――――――――――――――――――――――――――――――
Table 9

――――――――――――――――――――――――――――――――――――――――
No. R ¹ R ² R ³ R ⁴ AY ² G ² mp (℃)
――――――――――――――――――――――――――――――――――――――――
7-001 FF CH ₃ H CH H (G ² -1-a) -2-Cl-4-CF ₃ * 1
7-002 OCH ₃ HHH CH H (G ² -1-a) -2-Cl-4-CF ₃ * 1
7-003 FFHHNF (G ² -1-a) -2-Cl-4-CF ₃ 132-135
7-004 FFHHNH (G ² -1-a) -2-Cl-4-CF ₃ 91-94
――――――――――――――――――――――――――――――――――――――――
Table 10

――――――――――――――――――――――――――――――――――――――――
No. R ¹ R ² R ³ R ⁴ AY ² G ² mp (℃)
――――――――――――――――――――――――――――――――――――――――
8-001 -CH ₂ CH ₂ -HHNH (G ² -1-a) -2-Cl-4-CF ₃ * 1
8-002 HH CH ₃ HNH (G ² -1-a) -2-Cl-4-CF ₃ 166-169
――――――――――――――――――――――――――――――――――――――――
Table 11

――――――――――――――――――――――――――――――――――――――――
No. R ¹ R ² R ³ R ⁴ AY ² G ² mp (℃)
――――――――――――――――――――――――――――――――――――――――
9-001 FFHHNH (G ² -1-a) -4-CF ₃ * 1
――――――――――――――――――――――――――――――――――――――――
Table 12

――――――――――――――――――――――――――――――――――――――――
No. R ¹ R ² R ³ R ⁴ AY ² G ² mp (℃)
――――――――――――――――――――――――――――――――――――――――
10-001 FF CH ₃ H CH H (G ² -1-a) -2-Cl-4-CF ₃ * 1
――――――――――――――――――――――――――――――――――――――――
Table 13

――――――――――――――――――――――――――――――――――――――――
No. R ¹ R ² R ³ R ⁴ AY ² G ² mp (℃)
――――――――――――――――――――――――――――――――――――――――
11-001 FFHHNH (G ² -1-a) -4-CF ₃ 132-133
――――――――――――――――――――――――――――――――――――――――
Table 14

――――――――――――――――――――――――――――――――――――――――
No. R ¹ R ² R ³ R ⁴ AY ² G ² mp (℃)
――――――――――――――――――――――――――――――――――――――――
12-001 FFHHNH (G ² -1-a) -4-CF3 * 1
――――――――――――――――――――――――――――――――――――――――
Table 15

――――――――――――――――――――――――――――――――――――――――
No. R ¹ R ² R ³ R ⁴ AY ² G ² mp (℃)
――――――――――――――――――――――――――――――――――――――――
13-001 HHHHNH (G ² -1-a) -2-Cl-4-CF ₃ 101-104
13-002 FF CH ₃ H CH H (G ² -1-a) -2-Cl-4-CF ₃ 44-46
13-003 HHHHNH (G ² -1-a) -2,4-Cl ₂ 104-106
13-004 -CH ₂ CH ₂ -HHNH (G ² -1-a) -2-Cl-4-CF ₃ * 1
13-005 FFHHNH (G ² -1-a) -2,4-Cl ₂ 135-137
13-006 HH CH ₃ HNH (G ² -1-a) -2-Cl-4-CF ₃ * 1
13-007 OCH ₃ H CH ₃ H CH H (G ² -1-a) -2-Cl-4-CF ₃ * 1
13-008 HHHH CH H (G ² -1-a) -2-Cl-4-CF ₃ 90-92
13-009 OCH ₃ HHH CH H (G ² -1-a) -2-Cl-4-CF ₃ * 1
13-010 FFHHNH (G ² -1-a) -2-Cl-4-CF ₃ * 1
13-011 FFHHNF (G ² -1-a) -2-Cl-4-CF ₃ 124-127
13-012 FFHHNH (G ² -4-b) -6-Cl 171-172
13-013 FFHHNH (G ² -1-a) -4-CF ₃ 130-132
13-014 CH ₃ HHH CH H (G ² -1-a) -2-Cl-4-CF ₃ * 1
――――――――――――――――――――――――――――――――――――――――
Table 16

――――――――――――――――――――――――――――――――――――――――
No. R ¹ R ² R ³ R ⁴ AY ² G ² mp (℃)
――――――――――――――――――――――――――――――――――――――――
14-001 HHHHNH (G ² -1-a) -2-Cl-4-CF ₃ 106-110
14-002 -CH ₂ CH ₂ -HHNH (G ² -1-a) -2-Cl-4-CF ₃ * 1
14-003 FFHHNH (G ² -1-a) -2,4-Cl ₂ * 1
14-004 HH CH ₃ HNH (G ² -1-a) -2-Cl-4-CF ₃ * 1
14-005 OCH ₃ H CH ₃ H CH H (G ² -1-a) -2-Cl-4-CF ₃ * 1
14-006 HHHH CH H (G ² -1-a) -2-Cl-4-CF ₃ * 1
14-007 OCH ₃ HHH CH H (G ² -1-a) -2-Cl-4-CF ₃ * 1
14-008 FFHHNH (G ² -1-a) -2-Cl-4-CF ₃ * 1
14-009 FFHHNF (G ² -1-a) -2-Cl-4-CF ₃ * 1
14-010 FFHHNH (G ² -4-b) -6-Cl 119-122
14-011 FFHHNH (G ² -1-a) -4-CF ₃ * 1
14-012 CH ₃ HHH CH H (G ² -1-a) -2-Cl-4-CF ₃ * 1
14-013 FF CH ₃ H CH H (G ² -1-a) -2-Cl-4-CF ₃ * 1
――――――――――――――――――――――――――――――――――――――――
Of the compounds in Tables 3 to 16, ¹ H NMR data of compounds having no melting point in the table are shown in Table 17.
Table 17
-------------------------------------------------- -----------------------------
No. ¹ HNMR (CDCl ₃ , MeSi, 300MHz)
-------------------------------------------------- -----------------------------
1-003
δ8.25-8.30 (m, 1H), 8.00 (d, J = 2.4Hz, 1H), 7.40-7.70 (m, 8H), 7.25-7.35 (m, 1H), 7.15-7.20 (m, 2H), 5.89 (d, J = 10.5Hz, 1H), 5.30-5.50 (m, 1H), 1.34 (d, J = 6.6Hz, 3H).
1-005
δ8.50 (d, J = 2.1Hz, 1H), 8.25-8.30 (m, 1H), 8.00 (d, J = 2.1Hz, 1H), 7.82 (d, J = 2.1Hz, 7.40-7.65 (m, 6H), 7.15-7.20 (m, 2H), 6.18 (t, J = 5.1Hz, 1H), 3.74 (d, J = 5.1Hz, 2H), 1.10-1.15 (m, 4H).
1-006
δ8.50 (d, J = 2.1Hz, 1H), 8.25-8.30 (m, 1H), 8.00 (d, J = 2.1Hz, 1H), 7.82 (d, J = 2.1Hz, 1H), 7.40-7.70 (m, 6H), 7.15-7.20 (m, 2H), 6.76 (d, J = 8.1Hz, 1H), 4.70-4.80 (m, 1H), 3.15-3.30 (m, 2H), 1.33 (d, J = 6.6Hz, 3H).
1-007
δ8.54 (d, J = 1.8Hz, 1H), 7.99 (d, J = 2.4Hz, 1H), 7.95 (d, J = 1.5Hz, 1H), 7.80 (d, J = 2.4Hz, 1H), 7.65-7.70 (m, 1H), 7.55-7.60 (m, 5H), 7.15-7.20 (m, 2H), 6.46 (t, J = 6.6Hz, 1H), 4.47 (dt, J = 6.6, 13.5Hz, 2H).
1-008
δ8.25-8.30 (m, 1H), 7.95-8.00 (m, 1H), 7.15-7.70 (m, 11H), 6.22 and 6.05 (d, J = 8.7Hz, 1H), 4.79 and 4.66 (d, J = 3.9Hz, 1H), 4.45-4.65 (m, 1H), 3.32 amd 3.31 (s, 3H), 1.42 and 1.08 (d, J = 6.9Hz, 3H).
1-010
δ8.25-8.30 (m, 1H), 7.99 (d, J = 2.4Hz, 1H), 7.69 (dd, J = 1.5, 7.8Hz, 1H), 7.45-7.60 (m, 6H), 7.38 (dd, J = 7.8, 1.8Hz, 1H), 7.29 (d, J = 7.8Hz, 1H), 7.15-7.20 (m, 2H), 5.83 (t, J = 6.3Hz, 1H), 3.75 (td, J = 7.2 , 6.3Hz, 2H), 3.10 (t, J = 7.2Hz, 2H).
2-002
δ8.53 (d, J = 1.2Hz, 1H), 8.25-8.30 (m, 1H), 8.00 (d, J = 2.1Hz, 1H), 7.82 (d, J = 1.2Hz, 1H), 7.60-7.65 (m, 2H), 7.30-7.40 (m, 1H), 7.15-7.20 (m, 2H), 6.85-6.95 (m, 2H), 6.35-6.40 (m, 1H), 3.75 (d, J = 5.1Hz , 2H), 1.10-1.15 (m, 4H).
3-001
δ8.70-8.75 (m, 1H), 8.25-8.30 (m, 1H), 8.13 (d, J = 5.4Hz, 1H), 7.99 (d, J = 2.4Hz, 1H), 7.89 (d, J = 10.2Hz, 1H), 7.50-7.65 (m, 4H), 7.35-7.45 (m, 4H), 7.15-7.20 (m, 2H), 5.30-5.45 (m, 1H), 1.38 (d, J = 7.2Hz , 3H).
3-003
δ8.71 (dd, J = 4.8, 1.8Hz, 1H), 8.53 (d, J = 1.8Hz, 1H), 8.25-8.30 (m, 1H), 8.11 (d, J = 8.1, 1.8Hz, 1H) , 8.00 (d, J = 2.1Hz, 1H), 7.90-7.95 (m, 1H), 7.81 (d, J = 2.1Hz, 1H), 7.55-7.65 (m, 2H), 7.52 (dd, J = 8.1 , 4.8Hz, 1H), 7.15-7.20 (m, 2H), 3.77 (d, J = 5.7Hz, 2H), 1.10-1.15 (m, 4H).
3-008
δ8.76 (dd, J = 4.8, 1.5Hz, 1H), 8.25-8.30 (m, 1H), 8.17 (dd, J = 8.1, 1.5Hz, 1H), 7.95-8.00 (m, 2H), 7.55- 7.65 (m, 4H), 7.40-7.50 (m, 2H), 7.15-7.20 (m, 2H), 4.89 (dd, J = 8.1, 3.9Hz, 1H), 3.99 (ddd, J = 14.1, 7.5, 3.9 Hz, 1H), 3.48 (ddd, J = 14.1, 7.5, 4.8Hz, 1H), 3.34 (s, 3H).
4-001
δ8.45-8.50 (m, 1H), 8.25-8.30 (m, 1H), 7.95-8.15 (m, 2H), 7.81 and 7.76 (dd, J = 1.5, 8.4Hz, 1H), 7.25-7.60 (m , 6H), 7.15-7.20 (m, 2H), 4.81 and 4.74 (d, J = 4.2Hz, 1H), 4.45-4.65 (m, 1H), 3.35 (s, 3H), 1.41 and 1.12 (d, J = 6.9Hz, 1H).
5-001
δ8.75-8.80 (m, 1H), 8.25-8.30 (m, 1H), 7.95-8.00 (m, 1H), 7.40-7.75 (m, 2H), 7.15-7.25 (m, 2H), 5.94 (d , J = 9.0Hz, 1H), 5.35-5.50 (m, 1H), 1.34 (d, J = 7.2Hz, 3H).
6-002
δ8.45 (dd, J = 4.8, 2.1Hz, 1H), 8.25-8.30 (m, 1H), 8.00 (d, J = 2.1Hz, 1H), 7.90-8.00 (m, 1H), 7.55-7.65 ( m, 4H), 7.40-7.50 (m, 1H), 7.32 (dd, J = 7.2, 1.8Hz, 1H), 7.15-7.20 (m, 2H), 6.62 (d, J = 9.6Hz, 1H), 5.35 -5.50 (m, 1H), 1.40 (d, J = 6.9Hz, 3H).
6-007
δ8.40-8.50 (m, 2H), 8.25-8.30 (m, 1H), 8.11 and 7.93 (d, J = 2.1Hz, 1H), 7.95-8.00 (m, 1H), 7.55-7.60 (m, 3H ), 7.25-7.50 (m, 3H), 7.15-7.20 (m, 2H), 6.96 and 6.77 (d, J = 9.0Hz, 1H), 4.82 and 4.69 (d, J = 3.3Hz, 1H), 4.55- 4.65 (m, 1H), 3.36 and 3.35 (s, 3H), 1.45 and 1.11 (d, J = 6.9Hz, 3H).
7-001
δ8.81 (d, J = 2.4Hz, 1H), 8.75 (d, J = 2.4Hz, 1H), 8.25-8.30 (m, 1H), 7.99 (d, J = 2.1Hz, 1H), 7.50-7.65 (m, 4H), 7.35-7.45 (m, 2H), 7.15-7.20 (m, 2H), 5.30-5.55 (m, 1H), 1.38 (d, J = 6.9Hz, 3H).
7-002
δ8.81 (d, J = 2.4Hz, 1H), 8.76 (d. J = 2.4Hz, 1H), 8.25-8.30 (m, 1H), 7.99 (d, J = 2.1Hz, 1), 7.70-7.75 (m, 1H), 7.55-7.60 (m, 3H), 7.45-7.50 (m, 2H), 7.15-7.20 (m, 3H), 4.88 (dd, J = 7.8, 3.6Hz, 1H), 4.01 (ddd , J = 14.1, 7.5, 3.6Hz, 1H), 3.48 (ddd, J = 14.1, 7.5, 4.8Hz, 1H), 3.34 (s, 3H).
8-001
δ8.45-8.55 (m, 3H), 8.25-8.30 (m, 1H), 8.00 (d, J = 2.4Hz, 1H), 7.85-7.90 (m, 1H), 7.81 (d, J = 1.2Hz, 1H), 7.55-7.60 (m, 2H), 7.15-7.20 (m, 2H), 3.76 (d, J = 6.0Hz, 2H), 1.10-1.15 (m, 4H).
9-001
δ8.57 (d, J = 1.5Hz, 1H), 8.40-8.45 (m, 1H), 7.95 (d, J = 1.5Hz, 1H), 7.94 (dd, J = 8.7, 2.7Hz, 1H), 7.60 -7.65 (m, 2H), 7.46 (d, J = 5.4Hz, 1H), 7.24 (d, J = 5.4Hz, 1H), 7.15-7.25 (m, 2H), 7.07 (d, J = 8.7Hz, 1H), 7.00-7.05 (m, 1H), 4.45 (td, J = 13.2, 6.6 Hz, 2H).
10-001
δ8.27 (brs, 1H), 7.99 (d, J = 2.4Hz, 1H), 7.55-7.70 (m, 3H), 7.35-7.45 (m, 3H), 7.15-7.20 (m, 2H), 7.08 ( d, J = 5.1Hz, 1H), 6.25-6.35 (m, 1H), 5.30-5.50 (m, 1H), 1.39 (d, J = 6.9Hz, 3H).
12-001
δ8.58 (d, J = 1.5Hz, 1H), 8.40-8.45 (m, 1H), 7.95 (dd, J = 8.7, 2.7Hz, 1H), 7.93 (s, 1H), 7.92 (d, J = 1.5Hz, 1H), 7.60-7.65 (m, 2H), 7.15-7.20 (m, 2H), 7.10-7.15 (m, 1H), 7.07 (d, J = 8.7Hz, 1H), 6.78 (t, J = 54.6Hz, 1H), 4.42 (td, J = 13.2, 6.3Hz, 2H), 3.91 (s, 3H).
13-004
δ8.54 (d, J = 1.8Hz, 1H), 8.25-8.30 (m, 1H), 8.00 (d, J = 2.1Hz, 1H), 7.79 (d, J = 1.8Hz, 1H), 7.60-7.65 (m, 2H), 7.15 (m, 2H), 4.80-4.85 (m, 1H), 3.42 (d, J = 6.0Hz, 2H), 1.35 (s, 9H), 1.00-1.10 (m, 4H).
13-006
δ8.56 (d, J = 1.8Hz, 1H), 8.25-8.30 (m, 1H), 8.01 (d, J = 2.4Hz, 1H), 7.78 (d, J = 1.8Hz, 1H), 7.60-7.65 (m, 2H), 7.20-7.25 (m, 2H), 4.95-5.00 (m, 1H), 4.10-4.20 (m, 1H), 3.05-3.15 (m, 2H), 1.38 (s, 9H), 1.22 (d, J = 6.3Hz, 3H).
13-007
δ8.25-8.30 (m, 1H), 8.00 (d, J = 1.8Hz, 1H), 7.60-7.65 (m, 2H), 7.50-7.55 (m, 1H), 7.40-7.50 (m, 1H), 7.15-7.20 (m, 2H), 4.50-4.90 (m, 2H), 3.95-4.05 (m, 1H), 3.30 and 3.29 (s, 3H), 1.43 and 1.30 (s, 9H), 1.28 and 0.99).
13-009
δ8.25-8.30 (m, 1H), 8.00-8.05 (m, 1H), 7.60-7.65 (m, 2H), 7.50-7.55 (m, 1H), 7.40-7.45 (m, 2H), 7.15-7.20 (m, 2H), 4.80-4.90 (m, 2H), 3.30-3.55 (m, 1H), 3.29 (s, 3H), 3.15-3.25 (m, 1H), 1.42 (s, 9H).
13-010
δ8.58 (d, J = 1.8Hz, 1H), 8.25-8.30 (m, 1H), 8.00 (d, J = 2.1Hz, 1H), 7.92 (d, J = 1.8Hz, 1H), 7.60-7.65 (m, 2H), 7.20-7.25 (m, 2H), 5.10-5.15 (m, 1H), 4.10 (dt, J = 6.3, 12.0Hz, 2H), 1.41 (s, 9H).
13-014
δ8.25-8.30 (m, 1H), 7.99 (d, J = 1.5Hz, 1H), 7.55-7.60 (m, 2H), 7.53 (dd, J = 4.8, 1.5Hz, 1H), 7.40 (dd, J = 8.4, 2.1Hz, 1H), 7.10-7.25 (m, 3H), 4.40-4.45 (m, 1H), 3.20-3.55 (m, 3H), 1.31 (s, 9H), 1.26 (d, J = 6.9Hz, 3H).
14-002
δ8.58 (d, J = 1.8Hz, 1H), 8.25-8.30 (m, 1H), 8.01 (d, J = 1.8Hz, 1H), 7.81 (d, J = 1.8Hz, 1H), 7.60-7.65 (m, 2H), 7.15-7.20 (m, 2H), 2.98 (s, 2H), 1.65 (brs, 2H), 0.95-1.05 (m, 4H).
14-003
δ8.59 (d, J = 1.8Hz, 1H), 7.99 (d, J = 2.4Hz, 1H), 7.92 (d, J = 1.8Hz, 1H), 7.80 (d, J = 2.4Hz, 1H), 7.60-7.65 (m, 2H), 7.15-7.20 (m, 2H), 3.52 (t, J = 14.1Hz, 2H), 1.54 (brs, 2H).
14-004
δ8.51 (d, J = 1.8Hz, 1H), 8.25-8.30 (m, 1H), 7.99 (d, J = 2.1Hz, 1H), 7.81 (J = 1.8Hz, 1H), 7.55-7.65 (m , 2H), 7.15-7.20 (m, 2H), 3.85-3.90 (m, 1H), 3.27 (d, J = 6.6Hz, 2H), 1.49 (d, J = 6.6Hz, 3H).
14-005
δ8.25-8.30 (m, 1H), 7.99 (d, J = 2.1Hz, 1H), 7.55-7.60 (m, 3H), 7.40-7.50 (m, 2H), 7.15-7.20 (m, 2H), 4.50-4.70 (m, 1H), 3.15-3.35 (m, 1H), 3.31 and 3.25 (s, 3H), 1.10 and 1.08 (d, J = 6.9Hz, 3H).
14-006
δ8.25-8.30 (m, 1H), 7.99 (d, J = 2.1Hz, 1H), 7.50-7.60 (m, 3H), 7.30-7.40 (m, 1H), 7.15-7.25 (m, 3H), 3.90-3.05 (m, 4H), 2.05-2.10 (m, 2H).
14-007
δ8.25-8.30 (m, 1H), 8.00 (d, J = 1.8Hz, 1H), 7.55-7.60 (m, 2H), 7.50-7.55 (m, 1H), 7.40-7.50 (m, 2H), 7.15-7.20 (m, 2H), 4.65-4.70 (m, 1H), 3.33 (s, 3H), 2.85-3.05 (m, 2H), 1.92 (brs, 2H).
14-008
δ8.61 (d, J = 1.8Hz, 1H), 8.25-8.30 (m, 1H), 8.01 (d, J = 2.4Hz, 1H), 7.93 (d, J = 1.8Hz, 1H), 7.60-7.65 (m, 2H), 7.20-7.25 (m, 2H), 3.53 (t, J = 14.1Hz, 2H), 1.56 (br-s, 1H).
14-009
δ8.60 (d, J = 1.8Hz, 1H), 8.25-8.30 (m, 1H), 8.01 (d, J = 2.4Hz, 1H), 7.93 (d, J = 1.8Hz, 1H), 7.35-7.45 (m, 2H), 7.25-7.30 (m, 1H), 3.52 (t, J = 14.1Hz, 2H), 1.55 (brs, 2H).
14-011
δ8.59 (d, J = 1.8Hz, 1H), 8.40-8.45 (m, 1H), 7.90-7.95 (m, 2H), 7.60-7.65 (m, 2H), 7.15-7.25 (m, 2H), 7.07 (d, J = 8.4Hz, 1H), 3.56 (t, J = 13.5Hz, 2H), 1.95 (brs, 2H).
14-012
δ8.25-8.30 (m, 1H), 7.99 (d, J = 2.1Hz, 1H), 7.55-7.60 (m, 3H), 7.41 (dd, J = 8.1, 1.8Hz, 1H), 7.10-7.25 ( m, 3H), 3.45-3.60 (m, 3H), 3.12 (brs, 2H), 1.36 (d, J = 6.9Hz, 3H).
14-013
δ8.25-8.30 (m, 1H), 8.00 (d, J = 2.4Hz, 1H), 7.50-7.65 (m, 4H), 7.45-7.50 (m, 2H), 7.15-7.20 (m, 2H), 3.70-3.95 (m, 1H), 1.05-1.15 (m 3H).
-------------------------------------------------- -----------------------------
[Test example]
The usefulness of the compounds of the present invention as pest control agents will be specifically described by the following test examples, but the present invention is not limited to these examples.

  Preparation of test chemical solution A; emulsified white sample of the present compound (Solpol (registered trademark) 3005XL (manufactured by Toho Chemical Industry Co., Ltd.)): N-methylpyrrolidone: Solvesso (registered trademark) 200 (manufactured by ExxonMobil) = 1: 5: 2 mixture) to prepare a 20% by weight emulsion. Next, distilled water was added to dilute to a predetermined concentration (500 ppm), and this solution was subjected to the following Test Examples 1 to 8.

  Preparation of test drug solution B: The compound of the present invention was dissolved in dimethyl sulfoxide to prepare a 1% strength by weight solution. Next, distilled water was added to dilute to a predetermined concentration (100 ppm), and this solution was subjected to the following Test Examples 9-12.

Test Example 1 Cucumber Powdery Mildew Prevention 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; Erysihe 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 compounds tested, the following compounds showed a control value of 70% or more.
Compound No.1-002, 1-004, 1-005, 1-006, 1-013, 3-001, 3-003, 3-004, 3-006, 3-007, 5-002, 6 -001, 7-001, 10-001.

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. The conidial spore suspension of cucumber gray mold fungus (Botrytis cinerea) and the dissolved PDA medium were mixed at a ratio of 1: 1, and 30 μl of each of the treated leaves was 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 compounds tested, the following compounds showed a control value of 70% or more.
Compound of the present invention: No.1-001, 1-003, 1-004, 1-005, 1-006, 2-003, 1-007, 1-008, 1-011, 1-013, 1-014, 3-001, 3-003, 3-004, 3-006, 4-001, 3-007, 3-008, 3-010, 5-001, 6-002, 5-002, 6-003, 6- 004, 6-005, 6-006, 5-003, 6-007, 6-008, 6-009, 6-010, 6-011, 6-012, 7-001, 8-001, 8-002, 7-002, 7-003, 7-004, 10-001, 12-001.

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 a bacterial-containing agar piece (diameter 5 mm) of cucumber gray mold (Botrytis cinerea) previously cultured in PDA medium was inoculated into the cotyledons of drug-treated cucumber. After inoculation, the plastic container was covered with vinyl and humidified, and placed at 20 ° C. for 2 days. Thereafter, 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 compounds tested, the following compounds showed a control value of 70% or more.
Compound of the present invention: No.1-001, 1-003, 1-004, 1-005, 1-006, 1-007, 1-008, 1-011, 1-013, 1-014, 2-003, 3-001, 3-003, 3-004, 3-006, 3-007, 3-008, 3-010, 4-001, 5-001, 5-002, 5-003, 6-002, 6- 003, 6-004, 6-005, 6-006, 6-007, 6-008, 6-009, 6-010, 6-011, 6-012, 7-001, 7-002, 7-003, 7-004, 8-001, 8-002, 10-001, 12-001.

Test Example 4 Cucumber Nucleus Disease Prevention Effect Test Cucumber (variety: Sagamihanjiro) was planted in a 90 cm ³ plastic pot, and the test drug solution A of the compound of the present invention was diluted to a concentration of 500 ppm by adding distilled water at the cotyledon stage. 5 ml sprayed per pot. 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 compounds tested, the following compounds showed a control value of 70% or more.
Compound of the present invention: No.1-001, 1-003, 1-004, 1-005, 1-006, 1-007, 1-009, 1-011, 1-013, 1-014, 3-001, 3-002, 3-003, 3-004, 3-006, 3-007, 3-008, 3-010, 4-001, 5-001, 5-002, 5-003, 6-001, 6- 002, 6-003, 6-004, 6-005, 6-006, 6-007, 6-008, 6-009, 6-010, 6-011, 6-012, 7-001, 7-002, 7-003, 7-004, 8-001, 8-002, 10-001, 11-001, 12-001.

Test Example 5 Cucumber Anthrax Preventive Effect Test Cucumber (variety: Sagamihanjiro) was planted in a 90 cm ³ plastic pot, and test chemical solution A of the compound of the present invention was diluted to a concentration of 500 ppm by adding distilled water at the cotyledon stage. 5 ml spraying treatment was performed. 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 compounds tested, the following compounds showed a control value of 70% or more.
The compound of the present invention: No.1-001, 1-009, 4-001.

Test Example 6 Wheat powdery mildew prevention effect test 1.3 Test chemical solution A of the compound of the present invention was added to distilled water in a 90 cm ³ plastic pot planted with 1.3 leaves of wheat (variety: Norin 61), and the concentration was 500 ppm. And 5 ml sprayed per pot. 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 compounds tested, the following compounds showed a control value of 70% or more.
Compound of the present invention: No.1-001, 1-003, 1-004, 1-006, 1-007, 1-008, 1-009, 1-011, 1-014, 1-015, 3-001, 3-002, 3-003, 3-004, 3-006, 3-008, 3-010, 4-001, 5-001, 6-001, 6-002, 6-005, 6-006, 6- 011, 7-001, 7-002, 7-003, 8-001, 8-002, 10-001, 11-001, 12-001.

Test Example 7 Wheat Blight Prevention Effect Test 1.3 Distilled water was added to test chemical solution A of the present invention in a 90 cm ³ plastic pot planted with ³ leaf stage wheat (variety: Haruyutaka) to a concentration of 500 ppm. Then, 5 ml per pot was sprayed. 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 compounds tested, the following compounds showed a control value of 70% or more.
Compound of the present invention: No.1-001, 1-003, 1-006, 1-008, 1-011, 1-012, 1-013, 2-003, 3-001, 3-006, 3-008, 3-009, 3-010, 4-001, 5-001, 6-007, 6-009, 6-010, 6-011, 7-001, 7-002, 7-003, 7-004, 10- 001, 12-001.

Test Example 8 Antibacterial activity test against fungus mold After dispensing 60 μl of potato dextrose 1% agar medium to a 96-well plate, sterile water (10 spores / 3 μl) containing spores of Aspergillus niger was added. 30 μl was added per well. From this, test chemical solution B of the compound of the present invention was diluted with distilled water to a concentration of 10 ppm, added 10 μl per well, and allowed to stand at 25 ° C. under dark conditions. Evaluate the flora area ratio (%) 2 days after the addition of the drug,
%) 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, 1-008, 1-009, 1-010, 1-011, 1-012, 1-013, 1-014, 1-015, 2-003, 3-001, 3-003, 3-004, 3-006, 3-007, 3-008, 3-009, 3- 010, 3-011, 4-001, 5-001, 5-002, 5-003, 6-001, 6-002, 6-003, 6-004, 6-005, 6-006, 6-007, 6-008, 6-009, 6-010, 6-011, 6-012, 6-013, 7-001, 7-002, 7-003, 7-004, 8-001, 8-002, 10- 001, 12-001.

Test Example 9 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, the test drug solution B of the compound of the present invention was diluted with distilled water to a concentration of 1000 ppm, added 10 μl per 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, 1-003, 1-004, 1-005, 1-006, 1-007, 1-008, 1-009, 1-010, 1-011, 1-012, 1-013, 1-014, 1-015, 2-001, 2-002, 2-003, 3-001, 3-002, 3-003, 3-004, 3-005, 3-006, 3- 007, 3-008, 3-009, 3-010, 3-011, 4-001, 5-001, 5-002, 5-003, 6-001, 6-002, 6-003, 6-004, 6-005, 6-006, 6-007, 6-008, 6-009, 6-010, 6-011, 6-012, 6-013, 7-001, 7-002, 7-004, 8- 001, 8-002, 9-001, 10-001.

Test Example 10 Control Effect Test on Sweet Potato Nematode Cellulose-planted spinach seedlings (about 2 weeks after germination) filled with 10 g of soil per cell were added 300 ppm of test chemical solution B of the present compound with distilled water. Dilute to concentration and treat 1 ml per strain. 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.
Compound of the present invention: No.1-001, 1-003, 1-006, 1-007, 1-009, 1-013, 1-014, 3-001, 3-007, 3-010, 5-001, 6-001, 6-005, 6-008, 6-009, 6-010, 6-011, 6-012, 7-001, 7-002, 7-003, 7-004.

Test Example 11 Insecticidal test against 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, test chemical solution B of the compound of the present invention was diluted with distilled water to a concentration of 10 ppm, added 10 μl per 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, 1-008, 1-009, 1-010, 1-011, 1-012, 1-013, 1-014, 1-015, 2-001, 2-002, 2-003, 3-001, 3-002, 3-003, 3-004, 3-005, 3- 006, 3-007, 3-008, 3-009, 3-010, 3-011, 4-001, 5-001, 5-002, 5-003, 6-001, 6-002, 6-003, 6-004, 6-005, 6-006, 6-007, 6-008, 6-009, 6-010, 6-011, 6-012, 6-013, 7-001, 7-002, 7- 003, 7-004, 8-001, 8-002, 9-001, 10-001, 11-001, 12-001.

  The phenylacetylene-substituted amide compound according to the present invention exhibits excellent pest control activity, sometimes bactericidal / insecticidal activity, and has almost no adverse effect on non-target organisms such as mammals, fish and useful insects. It is a useful compound.

Claims (13)

Formula (I):

[In the formula, G ¹ represents a structure represented by G ¹ -1 to G ¹ -13;

G ² is represents a structure represented by G ² -1~G ² -4

A represents a nitrogen atom or CY ^A ,
X ¹ is a halogen atom, nitro, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ haloalkylthio, represents C ₁ -C ₄ haloalkylsulfinyl or C ₁ -C ₄ haloalkylsulfonyl,
X ² represents a hydrogen atom, a halogen atom or C ₁ -C ₄ alkyl,
X ³ represents a hydrogen atom or C ₁ -C ₄ alkyl,
Y ^A represents a hydrogen atom, a halogen atom or methyl,
Y ¹ represents a hydrogen atom, a halogen atom, C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl.
Y ² represents a halogen atom, cyano, nitro, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy or C ₁ -C ₆ haloalkoxy, and when m represents 2 or more Represents that each Y ² may be the same as or different from each other;
R ¹ and R ² are each independently a hydrogen atom, a halogen atom, cyano, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy or C ₁ -C ₄ alkoxy or a carbonyl, or by R ¹ and R ² form a C ₂ -C ₅ alkylene chain together, 3-6 membered ring together with the carbon to which R ¹ and R ² are bonded Represents the formation of
R ³ and R ⁴ each independently represent a hydrogen atom or C ₁ -C ₆ alkyl,
Alternatively, R ³ and R ⁴ together form an ethylene chain, thereby forming 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 ₆ alkyl, C ₁ -C ₆ haloalkyl, (C ₁ -C ₂ ) alkyl substituted by R ⁶ , C ₃ -C ₆ cycloalkyl, C ₂ -C ₆ alkenyl , C ₃ -C ₆ alkynyl, -OH, C ₁ ~C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ haloalkylthio, -C a (O) R ⁷ or C ₁ -C ₄ alkoxycarbonyl Represent,
R ⁶ represents cyano, C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkoxycarbonyl, -C (O) NH ₂ or -C (S) NH ₂
R ⁷ represents C ₁ -C ₄ alkyl or C ₁ -C ₄ alkoxymethyl,
Z is 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, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ represents alkylsulfonyl, C ₁ -C ₄ haloalkylthio, a C ₁ -C ₄ haloalkylsulfinyl or C ₁ -C ₄ haloalkylsulfonyl, when n is 2 or more, each of Z may be the same or different from each other, and when two Zs are adjacent, the two adjacent Zs together form -CH = CH-CH = CH- Thus, a hydrogen atom on —CH═CH—CH═CH— formed by two Z's may form a 6-membered ring with the carbon atom to which each Z is bonded, and may be replaced by R ⁸ . Represents
R ⁸ represents a halogen atom, C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl.
n represents an integer of 0, 1, 2, 3 or 4;
r represents an integer of 0, 1 or 2;
m represents an integer of 0, 1, 2, 3 or 4. ]
Or a N-oxide or a salt thereof. G ^{1 is, G 1 -1~G 1 -4, G} 1 -7, G 1 -8, represents G ¹ -10 or G ¹ -11,
G ² represents G ² -1 or G ² -4,
X ¹ represents a halogen atom or C ₁ -C ₄ haloalkyl,
X ² represents a hydrogen atom or a halogen atom,
X ³ represents methyl
Y ^A represents a hydrogen atom,
Y ¹ represents a halogen atom,
Y ² represents a halogen atom,
R ¹ and R ² each independently represent a hydrogen atom, a halogen atom, C ₁ -C ₆ alkyl or C ₁ -C ₆ alkoxy, or R ¹ and R ² together form an ethylene chain. Represents forming a cyclopropyl ring together with the carbon atom to which R ¹ and R ² are bonded,
R ³ and R ⁴ each independently represent a hydrogen atom or methyl, or R ³ and R ⁴ together form an ethylene chain, whereby a carbon atom to which R ³ and R ⁴ are bonded. Together with a cyclopropyl ring,
R ⁵ represents a hydrogen atom,
Z represents a halogen atom or a C ₁ -C ₄ haloalkyl, when n is 2, each Z is independently selected from groups or phases the same as each other, further, two Z are adjacent In some cases, two adjacent Z together form -CH = CH-CH = CH- to form a 6-membered ring with the carbon atom to which each Z is attached, and the two Z Represents that the hydrogen atom on —CH═CH—CH═CH— formed by may be substituted by R ⁸ ;
R ⁸ represents a halogen atom,
n represents an integer of 1 or 2,
m represents an integer of 0 or 1.
The phenylacetylene-substituted amide compound according to claim 1, its N-oxide or a salt thereof. Formula (II):

Wherein, G ² represents a G ² -1 or G ² -4,

A represents a nitrogen atom or CY ^A ,
Y ^A represents a hydrogen atom,
Y ¹ represents a halogen atom,
Y ² represents a halogen atom,
R ¹ and R ² each independently represent a hydrogen atom, fluorine, methyl or methoxy,
Alternatively, R ¹ and R ² together form an ethylene chain, thereby forming a cyclopropyl ring with the carbon atom to which R ¹ and R ² are bonded,
R ³ and R ⁴ each independently represents a hydrogen atom or methyl,
R ⁵ represents a hydrogen atom,
Z represents a halogen atom or a C ₁ -C ₄ haloalkyl, when n is 2, each Z is independently selected from groups or phases the same as each other, further, two Z are adjacent In some cases, two adjacent Z together form -CH = CH-CH = CH- to form a 6-membered ring with the carbon atom to which each Z is attached, and the two Z Represents that the hydrogen atom on —CH═CH—CH═CH— formed by may be substituted by R ⁸ ;
R ⁸ represents a halogen atom,
n represents an integer of 0, 1 or 2
m represents an integer of 0 or 1. ]
The production intermediate of the phenylacetylene substituted amide compound of Claim 1 thru | or 2 represented by these, its N-oxide, or those salts.   A pesticidal composition comprising as an active ingredient at least one selected from the phenylacetylene-substituted amide compounds according to claim 1 or 2, an N-oxide or a salt thereof.   An antifungal or parasite control agent composition for mammals or birds, comprising as an active ingredient at least one selected from the phenylacetylene-substituted amide compounds according to claim 1 or 2, an N-oxide or a salt thereof. .   The antifungal agent or parasite control agent composition according to claim 5 for oral administration to mammals or birds.   The antifungal or parasite control composition according to claim 5 for parenteral administration to mammals or birds.   The antifungal agent or parasite control agent composition according to claim 7, wherein the parenteral administration to mammals or birds is administration by injection.   The antifungal agent or parasite control agent composition according to claim 7, wherein the parenteral administration to mammals or birds is transdermal administration.   An agricultural or horticultural fungicide or nematicide composition comprising, as an active ingredient, one or more selected from the phenylacetylene-substituted amide compounds according to claim 1 or 2, an N-oxide or a salt thereof.   The agricultural and horticultural fungicide or nematicide composition according to claim 10 for spraying foliage on plants.   The agricultural and horticultural fungicide or nematicide composition according to claim 10 for treating soil on which plants grow. The agricultural or horticultural fungicide or nematicide composition according to claim 10 for treating plant seeds, tuberous roots and rhizomes.