JP2020029402A - Alkylphenyl-substituted amide compound and pest control agent - Google Patents

Abstract

To provide a novel pest control agent, in particular, a bactericide and a nematicide.SOLUTION: An alkylphenyl-substituted amide compound represented by formula (I), or a salt thereof, and a pest control agent containing the same are provided. In the formula (I), Gstands for a structure represented by G-2, G-3, G-4 or the like; Xstands for a halogen atom, difluoromethyl, trifluoromethyl or the like; Yis H, halogen, alkyl or the like; Yis H, halogen, cyano, or the like; Rstands for halogen, alkyl, alkoxy or the like; Rstands for H, halogen or alkyl; Rstands for H, alkyl or haloalkyl; Rstands for H or alkyl; Rstands for H, alkyl, cycloalkyl or the like; Rstands for H, halogen, (Z)-substituted phenyl, or the like; Z stands for halogen, alkyl, haloalkyl, alkoxy, cyano, nitro, SFor the like.SELECTED DRAWING: None

Description

  The present invention relates to a novel alkynylphenyl-substituted amide compound and a salt thereof, and a pesticidal agent containing the compound as an active ingredient.

  Conventionally, for alkynylphenyl-substituted amide compounds, for example, (E) -N- [2- [2-chloro-4- (1-propynyl) phenyl] -2-methoxyimino-1-methylethyl] -3- ( (Trifluoromethyl) pyridine-2-carboxamide, (E) -N- [2- [2-chloro-4- (cyclopropylethynyl) phenyl] -2-methoxyimino-1-methylethyl] -2- (difluoromethyl ) Nicotinamide, (E) -N- [2- [2-chloro-4- (1-propynyl) phenyl] -2-methoxyimino-1-methylethyl] -3- (trifluoromethyl) pyrazine-2- Carboxamide and the like exhibit fungicidal and nematicidal activity (see Patent Document 1), N- [2- [4- (3,3-dimethyl-1-butynyl) -2-methylphenyl] -1,1- Dimethyl-2-oxoethyl] -3-methylthiophene 2-Carboxamide, N- [2- [2-methyl-4- (trimethylsilylethynyl) phenyl] -1,1-dimethyl-2-oxoethyl] -3-methylthiophen-2-carboxamide and N- [2- It is known that [2-methyl-4- (phenylethynyl) phenyl] -1,1-dimethyl-2-oxoethyl] -3-methylthiophene-2-carboxamide exhibits bactericidal activity (see Patent Document 2). I have.

  In addition, N- [2- [4- (4-ethoxyphenylethynyl) phenyl] -1-methylethyl] benzamide and the like have acetyl-CoA carboxylase inhibitory activity (see Patent Document 3), and (R) -3-. [3-Fluoro-4- (cyclopropylethynyl) phenyl] -2- (2-fluoro-4-methylbenzamide) propionic acid and the like have a GLP-1 receptor modulating action (see Patent Document 4), (S) -3- [4- [3- (2-Pyridylaminomethyl) -1-propynyl] phenyl] -2- (2,6-dichlorobenzamide) propionic acid and the like having α5β1 integrin antagonist activity (Patent Document 5) ) And 1- [5- [2- (5-chloro-2-methoxybenzamido) ethyl] -2-ethynylbenzenesulfonyl] -3-methylthiourea are KATP channels. Having a rocker activity (see Non-Patent Document 1.) Is known.

  Furthermore, (S) -3- (4-ethynylphenyl) -2- (2,4,6-trimethylbenzamide) -tert-butyl propionate is used as an intermediate for producing an α5β1 integrin antagonist (see Patent Document 6). .) Are also known.

  However, the alkynylphenyl-substituted amide compounds according to the present invention are not disclosed at all, and their usefulness as pesticides is not known.

International Publication No. 2014-010737 International Publication No. 2006-016708 International Publication No. 2012-028676 International Publication No. 2011-097300 International Publication No. 2007-141473 International Publication No. 2007-131964

Journal of Medicinal Chemistry [J. Med. Chem.] 2001, 44, 1085

  Infection and parasitism of pests such as pathogens and parasites can occur when the host is a plant such as cereals, fruit trees, vegetables, ornamental plants, etc., when the quality of crops is reduced, the yield is significantly reduced, and in some cases, the plants die. It causes serious economic losses not only to producers but also to consumers. Therefore, effective control of these pests is a very important issue to achieve efficient and stable crop production. When the host is a companion animal, companion animal, livestock, poultry, or other animal, for the purpose of maintaining the health of the target animal, if the target animal is a livestock, poultry, etc. Effective control of these pests is also an important issue from the viewpoint of stably producing safe food and living materials such as high-quality wool, feathers and leather. From such a viewpoint, development of pesticidal agents for controlling pathogenic bacteria and parasites has been progressed, and many effective agents have been put to practical use to date.

  However, due to the long-term use of such agents, pathogens and parasites have acquired drug resistance in recent years, and it has become increasingly difficult to control them with existing pesticides that have been conventionally used. In addition, the problem that some of the existing pesticides are highly toxic, or some of them remain in the environment for a long period of time and disturb the ecosystem, is becoming apparent. Under such circumstances, the development of a novel pesticide and an effective control method that not only has excellent control activity against pathogenic bacteria and parasites but also has high control properties such as low toxicity and low persistence are constantly being developed. Expected.

  The present inventors have conducted intensive studies with the aim of solving the above-mentioned problems, and as a result, the novel alkynylphenyl-substituted amide compound represented by the following formula (I) has excellent pest control activity, especially antifungal and killing activity The present invention has been found to be an extremely useful compound that exhibits insect activity and has almost no adverse effect on non-target organisms such as plants, mammals, fish, useful insects, and natural enemies.

  That is, the present invention relates to the following [1] to [22].

[1]
An alkynylpyridine-substituted amide compound represented by the formula (I), an N-oxide or a salt thereof.

Wherein, G ¹ represents a structure represented by G ¹ -1~G ¹ -7,

X ¹ is a halogen atom, cyano, nitro, C ₁ -C ₄ alkyl, C ₁ -C ₃ haloalkyl, C ₁ -C ₃ alkoxy, C ₁ -C ₃ haloalkoxy, C ₁ -C ₃ alkylthio, C ₁ -C ₃ C ₃ alkylsulfinyl, C ₁ -C ₃ alkylsulfonyl, C ₁ -C ₃ represents a haloalkylthio or _C 1 -C ₃ haloalkylsulfonyl,
X ² represents a hydrogen atom or a halogen atom,
Y ¹ represents a hydrogen atom, a halogen atom, nitro, C ₁ -C ₄ alkyl, C ₁ -C ₃ haloalkyl, C ₁ -C ₃ alkoxy, C ₁ -C ₃ haloalkoxy or C ₁ -C ₃ alkylthio,
Y ² represents a hydrogen atom, a halogen atom, cyano or methyl,
R ¹ represents a hydrogen atom, a halogen atom, cyano, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, phenyl _(C 1 _{~C 4)} alkyl, _(Z) phenyl substituted by _{m (C} 1 -C ₄₎ alkyl, C ₃ -C ₆ cycloalkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, C ₃ -C ₆ alkenyloxy, C ₃ -C ₆ haloalkenyloxy, C ₃ -C ₆ alkynyloxy, C ₃ -C ₆ haloalkynyloxy, cyano _(C 1 ~C ₄₎ alkoxy, phenyl _(C 1 ~C ₄₎ alkoxy, by _{(Z) m} substituted phenyl _(C 1 _{~C 4)} alkoxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ haloalkylthio, C ₁ -C ₆ alkoxy amino, -C (O) NH ₂ or -C (S) NH ₂
R ² represents a hydrogen atom, a halogen atom or C ₁ -C ₆ alkyl,
Alternatively, R ¹ and R ² together form a C ₂ -C ₅ alkylene chain to form a 3- to 6-membered ring together with the carbon atom to which R ¹ and R ² are attached. chain represents the oxygen atom, may contain one to two sulfur atom or a nitrogen atom, and C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, may be optionally substituted by oxo or thioxo,
R ³ represents a hydrogen atom, C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
R ⁴ represents 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 attached;
R ⁵ is a hydrogen atom, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, (C ₁ -C ₂ ) alkyl substituted by R ⁷ , C ₃ -C ₆ cycloalkyl, C ₂ -C ₄ alkenyl , C ₃ -C ₄ alkynyl, -OH, C ₁ ~C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ haloalkylthio, -C a (O) ^{R 8} or _C 1 -C ₄ alkoxycarbonyl Represent
R ⁶ is a hydrogen atom, a halogen atom, a C ₁ -C ₆ alkyl, a C ₁ -C ₆ haloalkyl, a (C ₁ -C ₄ ) alkyl optionally substituted with R ⁹ , a C ₃ -C ₁₀ cycloalkyl, ₃ -C ₁₀ halocycloalkyl, C ₃ -C ₆ cycloalkyl _(C 3 ~C ₆₎ cycloalkyl, hydroxy _(C 3 ~C ₆₎ cycloalkyl, C ₁ -C ₂ alkoxy _(C 3 ~C ₆₎ cycloalkyl alkyl, phenyl _(C 3 -C ₆₎ cycloalkyl, C ₄ -C ₁₀ cycloalkenyl, C ₄ -C ₁₀ halo cycloalkenyl, tri _(C 1 -C ₄ alkyl) silyl, phenyl dimethylsilyl, -C ^{(R 10} ) = NOR ¹¹ , phenyl, phenyl substituted by (Z) _m or D-1 to D-29,
D-1 to D-29 each represent an aromatic heterocyclic ring represented by the following structural formula,

Z is a halogen atom, cyano, nitro, -SF _5, C ₁ ~C ₄ alkyl, C ₁ -C ₄ haloalkyl, cyano _(C 1 _{~C 4)} alkyl, C ₁ -C ₄ alkoxy _(C 1 -C ₄ ) Alkyl, C ₁ -C ₄ haloalkoxy (C ₁ -C ₄ ) alkyl, C ₁ -C ₄ alkylthio (C ₁ -C ₄ ) alkyl, C ₁ -C ₄ alkylsulfinyl (C ₁ -C ₄ ) alkyl, C ₁ -C ₄ alkylsulfonyl _(C 1 _{~C 4)} alkyl, C ₁ -C ₄ haloalkylthio _(C 1 _{~C 4)} alkyl, C ₁ -C ₄ haloalkylsulfinyl _(C 1 _{~C 4)} alkyl, C ₁ -C ₄ haloalkylsulfonyl _(C 1 ~C ₄₎ alkyl, C ₃ -C ₄ cycloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkyl sulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ Haroaru In the case where m represents 1 or more, and m or n represents 2 or more, represents thiothio, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ haloalkylsulfonyl, di (C ₁ -C ₄ alkyl) amino, phenyl or D-30 to D-38. the, each Z is independently selected from groups or different from each other be identical to each other, further, when two Z are adjacent, the two adjacent Z is -CH ₂ CH ₂ CH 2 _-, - CH ₂ CH ₂ O—, —CH ₂ OCH ₂ —, —OCH ₂ O—, —CH ₂ CH ₂ S (O) _r —, —CH ₂ S (O) _r CH ₂ —, —SCH ₂ S—, -CH ₂ CH ₂ CH ₂ CH _2- , -CH ₂ CH ₂ CH ₂ O-, -CH ₂ CH ₂ OCH _2- , -CH ₂ OCH ₂ O-, -OCH ₂ CH ₂ O-, -CH ₂ CH ₂ CH ₂ S (O) _r- , -CH ₂ CH ₂ S (O) _r CH _2- , -OCH ₂ CH ₂ S-, -SCH ₂ CH ₂ S-, -OCH = CH-, -SCH = CH _{-, - SO 2 CH = CH} -, - N (R 12) CH = CH -, - OCH = N -, - SCH = N -, - N (R 12) CH = N -, - ON = CH-, _{-SN = CH -, - SO 2} N = CH -, - N (R 12) N = CH -, - ON = N -, - SN = N -, - N (R 12) N = N- = NOCH =, = NSCH =, = = NN (R 12) CH, = NON =, = NSN =, = NN (R 12) N =, - CH = CHCH = CH -, - N = CHCH = CH-, -CH = NCH = CH-, -N = NCH = CH-, -N = CHN = CH-, -N = CHCH = N-, -CH = NN = CH- or -N = NCH = N- Thus, a 5- or 6-membered ring may be formed together with the carbon atom to which each Z is bonded, wherein the hydrogen atom bonded to each carbon atom forming the ring is a halogen atom, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, may be optionally substituted by C ₁ -C ₄ haloalkoxy or _C 1 -C ₄ haloalkylthio,
D-30 to D-38 each represent an aromatic heterocycle represented by the following structural formula,

Z ^a is a halogen atom, cyano, methyl, difluoromethyl, trifluoromethyl, cyclopropyl, methoxy or trifluoromethylsulfonyl, in the case where n is 2 or more, each Z ^a are the same to each other Or may be different from each other,
R ⁷ is cyano, C ₃ -C ₆ cycloalkyl, —OR ¹³ , C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkoxycarbonyl, —C (O) NH ₂ , —C (S) NH ₂ , phenyl , (Z) represents phenyl or D-23 substituted by _m ,
R ⁸ represents C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxymethyl, C ₃ -C ₄ cycloalkyl or C ₂ -C ₄ alkenyl,
R ⁹ represents cyano, —OR ¹⁴ , —S (O) _r R ¹⁵ or —N (R ¹⁷ ) R ¹⁶ ;
R ¹⁰ represents a hydrogen atom or C ₁ -C ₄ alkyl,
R ¹¹ represents C ₁ -C ₄ alkyl,
R ¹² is a hydrogen atom, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₃ -C ₄ cycloalkylmethyl, C ₃ -C ₄ halocycloalkylmethyl, C ₃ -C ₄ cycloalkyl or C ₃ -C ₄ represents halo cycloalkyl,
R ¹³ represents C ₁ -C ₄ alkyl, C ₂ -C ₄ haloalkyl, C ₁ -C ₄ alkylcarbonyl, C ₃ -C ₆ cycloalkylcarbonyl or C ₁ -C ₄ alkoxycarbonyl,
R ¹⁴ is a hydrogen atom, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy (C ₁ -C ₂ ) alkyl, E-1, E-2, C ₃ -C ₄ alkenyl , C ₃ -C ₄ represents haloalkenyl, C ₃ -C ₄ alkynyl, C ₃ -C ₄ haloalkynyl, phenyl substituted by phenyl or _{(Z) m,}
E-1 and E-2 each represent a saturated heterocyclic ring represented by the following structural formula,

R ¹⁵ is C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy (C ₁ -C ₂ ) alkyl, C ₃ -C ₄ alkenyl, C ₃ -C ₄ haloalkenyl, C ₃ -C ₄ represents alkynyl, C ₃ -C ₄ haloalkynyl, phenyl substituted by phenyl or _{(Z) m,}
R ¹⁶ and R ¹⁷ are each independently a hydrogen atom, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy (C ₁ -C ₂ ) alkyl, C ₃ -C ₄ alkenyl, Stands for C ₃ -C ₄ alkynyl, phenyl or phenyl substituted by (Z) _m ,
Alternatively, R ¹⁶ and R ¹⁷ may together form a C ₂ -C ₅ alkylene chain to form a 3- to 6-membered ring with the nitrogen atom to which R ¹⁶ and R ¹⁷ are attached. Wherein the alkylene chain may contain one oxygen atom or sulfur atom, and may be optionally substituted by C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, oxo or thioxo,
R ¹⁸ represents C ₁ -C ₄ alkyl, and when p represents 2, each R ¹⁸ may be the same as or different from each other;
m represents 1, 2, 3, 4 or 5;
n represents 0, 1, 2, 3, or 4;
p represents 0, 1 or 2;
r represents 0, 1 or 2. ]
[2]
X ¹ represents a halogen atom, nitro, methyl, difluoromethyl, trifluoromethyl, methylsulfonyl, difluoromethylsulfonyl or trifluoromethylsulfonyl,
X ² represents a hydrogen atom, a fluorine atom or a chlorine atom,
Y ¹ represents a halogen atom, methyl or methoxy,
Y ² represents a hydrogen atom, a fluorine atom, a chlorine atom or methyl,
R ¹ is a hydrogen atom, a fluorine atom, a C ₁ -C ₃ alkyl, a C ₁ -C ₃ haloalkyl, a benzyl, a phenylmethyl, a cyclopropyl, a C ₁ -C ₃ alkoxy, a C ₁ -C ₃ substituted by (Z) _m . C ₃ haloalkoxy, C ₃ -C ₄ alkenyloxy, C ₃ -C ₄ alkynyloxy, cyano, methoxy, benzyloxy, _(Z) phenylmethoxy substituted by _m, C ₁ -C ₃ alkylthio or _C 1 -C ₃ Represents haloalkylthio,
R ² represents a hydrogen atom, a fluorine atom or C ₁ -C ₃ alkyl,
Alternatively, R ¹ and R ² together form an ethylene chain, thereby forming a cyclopropyl ring together with the carbon atom to which R ¹ and R ² are attached;
R ³ represents a hydrogen atom, C ₁ -C ₃ alkyl or C ₁ -C ₃ haloalkyl,
R ⁴ represents a hydrogen atom or C ₁ -C ₃ 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 attached;
R ⁵ is hydrogen atom, C ₁ -C ₄ alkyl, (C ₁ -C ₂ ) alkyl substituted by R ⁷ , C ₃ -C ₆ cycloalkyl, C ₂ -C ₄ alkenyl, C ₃ -C ₄ alkynyl , C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkylthio, —C (O) R ⁸ or C ₁ -C ₄ alkoxycarbonyl,
R ⁶ is a hydrogen atom, a halogen atom, a C ₁ -C ₄ alkyl, a C ₁ -C ₄ haloalkyl, a (C ₁ -C ₄ ) alkyl optionally substituted by R ⁹ , a C ₃ -C ₆ cycloalkyl, ₃ -C ₆ halocycloalkyl, hydroxy _(C 3 ~C ₆₎ cycloalkyl, C ₁ -C ₂ alkoxy _(C 3 ~C ₆₎ cycloalkyl, C ₄ -C ₆ cycloalkenyl, tri _(C 1 -C ₄ Alkyl) silyl, -C (R ¹⁰ ) = NOR ¹¹ , phenyl, phenyl substituted by (Z) _m , D-1, D-2, D-6, D-8, D-23, D-24, Represents D-25 or D-26,
Z is a halogen atom, cyano, nitro, -SF _5, 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 alkylsulfonyl, C ₁ -C ₄ haloalkylthio, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ haloalkylsulfonyl, D-31~D-35 or D- 37, and when m or n represents 2 or more, each Z may be the same or different from each other, and when two Zs are adjacent, the adjacent 2 One of Z is _{-CH 2 CH 2 CH 2 -,} - CH 2 CH 2 O -, - CH 2 OCH 2 -, - OCH 2 O -, - CH 2 CH 2 S (O) r -, - CH 2 CH 2 CH ₂ CH ₂ —, —CH ₂ CH ₂ CH ₂ O—, —CH ₂ CH ₂ OCH ₂ —, —CH ₂ OCH ₂ O—, —OCH ₂ CH ₂ O—, —CH ₂ CH ₂ CH ₂ S ( O) _r- , -CH ₂ CH ₂ S (O) _r CH _2- , -OCH = CH-, -SCH = CH-, -N (R ¹² ) CH = CH-, -OCH = N-, -SCH = N-, -N (R ¹² ) CH = N -, - ON = CH -, - SN = CH -, - N (R 12) N = CH -, - SN = N -, - N (R 12) N = N -, = NN (R 12) CH =, = NON =, = NSN =, -CH = CHCH = CH-, -N = CHCH = CH-, -CH = NCH = CH-, -N = NCH = CH-, -N = CHN = CH- , -N = CHCH = N-, -CH = NN = CH- or -N = NCH = N- to form a 5- or 6-membered ring with the carbon atom to which each Z is attached. At this time, the hydrogen atom bonded to each carbon atom forming a ring may be optionally substituted by a halogen atom, cyano, methyl, difluoromethyl, trifluoromethyl or methoxy,
Z ^a represents a halogen atom, methyl or trifluoromethyl,
R ⁷ represents cyano, C ₃ -C ₆ cycloalkyl, —OR ¹³ , C ₁ -C ₄ alkylthio, —C (O) NH ₂ or —C (S) NH ₂ ;
R ⁸ represents C ₁ -C ₄ alkyl or C ₃ -C ₄ cycloalkyl,
R ⁹ represents —OR ¹⁴ or —S (O) _r R ¹⁵ ;
R ¹⁰ represents a hydrogen atom or methyl,
R ¹¹ represents methyl or ethyl,
R ¹² represents C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₃ -C ₄ cycloalkylmethyl or C ₃ -C ₄ cycloalkyl,
R ¹³ represents C ₁ -C ₄ alkyl or C ₂ -C ₄ haloalkyl;
R ¹⁴ represents a hydrogen atom, methyl, ethyl or C ₁ -C ₂ haloalkyl;
R ¹⁵ represents methyl, ethyl or C ₁ -C ₂ haloalkyl;
[1] The alkynylphenyl-substituted amide compound according to [1], its N-oxide or a salt thereof.

[3]
G ^{1 is, G 1 -1, G 1 -2} , G 1 -3, represents a structure represented by G ¹ -4 or ^{G 1} -7,
X ¹ represents a halogen atom, difluoromethyl, trifluoromethyl or methylsulfonyl,
X ² represents a hydrogen atom,
Y ¹ represents a halogen atom,
Y ² represents a hydrogen atom or a chlorine atom,
R ¹ represents a hydrogen atom, a fluorine atom or methoxy,
R ² represents a hydrogen atom or a fluorine atom,
R ³ represents a hydrogen atom or methyl,
R ⁴ represents a hydrogen atom,
R ⁵ represents a hydrogen atom,
R ⁶ represents C ₃ -C ₆ cycloalkyl, phenyl substituted by (Z) _m , D-1, D-2, D-6, D-23 or D-25;
Z represents a halogen atom or trifluoromethyl, and when n represents 2, each Z may be the same or different from each other, and further, when two Z are adjacent to each other, May form a 6-membered ring together with the carbon atom to which each Z is attached by forming two adjacent Zs to form -CH = CHCH = CH-,
R ¹² represents C ₁ -C ₄ alkyl;
m represents 1,
n represents 0, 1 or 2;
[2] The alkynylphenyl-substituted amide compound according to [2], its N-oxide or a salt thereof.

[4]
G ¹ represents a structure represented by G ¹ -1;
X ¹ represents trifluoromethyl,
X ² represents a hydrogen atom;
The alkynylphenyl-substituted amide compound according to [1] to [3], an N-oxide thereof or a salt thereof.

[5]
G ¹ represents a structure represented by G ¹ -2 or G ¹ -3,
X ¹ represents a halogen atom, difluoromethyl, trifluoromethyl or methylsulfonyl,
The alkynylphenyl-substituted amide compound according to [1] to [3], an N-oxide thereof or a salt thereof.

[6]
G ¹ represents a structure represented by G ¹ -4,
X ¹ represents a halogen atom or trifluoromethyl,
The alkynylphenyl-substituted amide compound according to [1] to [3], an N-oxide thereof or a salt thereof.

[7]
G ¹ represents a structure represented by G ¹ -7,
X ¹ represents trifluoromethyl,
r represents 0,
The alkynylphenyl-substituted amide compound according to [1] to [3], an N-oxide thereof or a salt thereof.

[8]
R ⁶ represents C ₃ -C ₆ cycloalkyl;
The alkynylphenyl-substituted amide compound according to [1] to [7], an N-oxide or a salt thereof.

[9]
R ⁶ represents phenyl substituted by (Z) _m ;
Z represents a halogen atom,
m represents 1.
The alkynylphenyl-substituted amide compound according to [1] to [7], an N-oxide or a salt thereof.

[10]
R ⁶ represents phenyl substituted by (Z) _m ;
m represents 2 or 3,
Z has at least two adjacent positions, and two adjacent Zs together form -CH ₂ CH ₂ CH _2- , -CH ₂ CH ₂ O-, -OCH ₂ O-, -OCH ₂ CH _{2 O -, - OCH = CH} -, - SCH = CH -, - N (R 12) CH = CH -, - OCH = N -, - SCH = N -, - N (R 12) CH = N-, -ON = CH -, - SN = CH -, - N (R 12) N = CH -, - N (R 12) N = N -, = = NN (R 12) CH, = NON = or = NSN = To form a 5- or 6-membered ring together with the carbon atom to which each Z is bonded, wherein the hydrogen atom bonded to each carbon atom forming the ring is a halogen atom, methyl Or may be optionally substituted by trifluoromethyl, and when m represents 3, the remaining Z represents a halogen atom, cyano, methyl, trifluoromethyl, methoxy, difluoromethoxy or trifluoromethoxy. ,
R ¹² represents C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl,
The alkynylphenyl-substituted amide compound according to [1], [2] or [4] to [7], an N-oxide or a salt thereof.

[11]
R ⁶ represents D-1, D-2, D-6, D-8, D-23 or D-25;
Z represents a halogen atom, methyl or trifluoromethyl, and when n represents 2, each Z may be the same or different from each other, and two Zs are adjacent In such a case, two adjacent Zs may form a 6-membered ring together with the carbon atom to which each Z is attached by forming -CH = CHCH = CH-,
R ¹² represents C ₁ -C ₄ alkyl;
n represents 0, 1 or 2;
The alkynylphenyl-substituted amide compound according to [1], [2] or [4] to [7], an N-oxide or a salt thereof.

[12]
The alkynylpyridine-substituted amide compound according to any one of [1] to [11] represented by the following formula (II), an N-oxide thereof, or a production intermediate thereof:

[Wherein, Y ¹ represents a halogen atom,
Y ² represents a hydrogen atom,
R ¹ represents a hydrogen atom or a fluorine atom,
R ² represents a hydrogen atom or a fluorine atom,
R ³ represents a hydrogen atom or methyl,
R ⁴ represents a hydrogen atom,
R ⁵ represents a hydrogen atom,
R ⁶ represents D-1, D-2, D-6, D-23 or D-25;
Z represents a halogen atom or trifluoromethyl, and when n represents 2, each Z may be the same or different from each other, and further, when two Z are adjacent to each other, May form a 6-membered ring together with the carbon atom to which each Z is attached by forming two adjacent Zs to form -CH = CHCH = CH-,
R ¹² represents C ₁ -C ₄ alkyl;
n represents 0, 1 or 2. ]
[13]
A pesticidal composition comprising, as an active ingredient, at least one selected from the alkynylphenyl-substituted amide compounds according to [1] to [11], and N-oxides or salts thereof.

[14]
An antifungal or parasiticidal composition for mammals or birds, comprising as an active ingredient at least one selected from the alkynylphenyl-substituted amide compounds according to [1] to [11], and N-oxides or salts thereof.

[15]
The antifungal or parasite control composition of [14] for oral administration to mammals or birds.

[16]
The antifungal or parasite control composition of [14] for parenteral administration to mammals or birds.

[17]
The antifungal or parasiticidal composition according to [16], wherein the method of parenteral administration to mammals or birds is administration by injection.

[18]
The antifungal or parasite control composition according to [16], wherein the method of parenteral administration to mammals or birds is transdermal administration.

[19]
A fungicide or nematicide composition for agricultural and horticultural use, comprising as an active ingredient at least one selected from the alkynylphenyl-substituted amide compounds according to [1] to [11], and N-oxides or salts thereof.

[20]
The fungicide or nematicide composition for agricultural and horticultural use according to [19], which is used for spraying foliage on plants.

[21]
The fungicide or nematicide composition for agricultural and horticultural use according to [19], for treating soil in which plants grow.

[22]
The agricultural or horticultural fungicide or nematicide composition according to [19], which is used for treating plant seeds, tubers and rhizomes.

  The compound of the present invention represented by the formula (I) and a pesticidal agent containing the compound as an active ingredient are excellent in controlling pests in the fields of agriculture and horticulture or livestock and sanitation, particularly fungi and nematodes. It exerts an effect and exerts a sufficient control effect on those pests that have acquired resistance to existing drugs. Furthermore, it has almost no adverse effect on non-target organisms such as plants, mammals, fish, useful insects, and natural enemies, and has low persistence and a light load on the environment.

  Therefore, the present invention can provide a useful novel pesticide.

  In the alkynylphenyl-substituted amide compound represented by the formula (I) included in the present invention, depending on the substituent, an optically active compound due to the presence of one or more asymmetric carbon atoms may be present. However, the present invention includes all optically active or racemic forms. In addition, in the compounds included in the present invention, depending on the substituent, E-form and Z-form geometric isomers may be present, but the present invention relates to these E-forms, Z-forms or E-forms. And a mixture containing Z-isomer in any ratio.

  As used herein, the following terms or expressions are used with the following meanings or usages, respectively.

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

  In the specific description of the substituents, the notation "n-" is "normal", "i-" is "iso", "sec-" is "secondary", and "tert-" is "tertiary". Lee "respectively.

The notation “C _a -C _b alkyl” represents a straight-chain or branched-chain hydrocarbon having ab carbon atoms, for example, methyl, ethyl, n-propyl, i-propyl, n- Butyl, i-butyl, sec-butyl, tert-butyl, pentyl, 1-ethylpropyl, 2,2-dimethylpropyl, hexyl, etc. are given as specific examples, each being selected within the range of the specified number of carbon atoms. .

The notation of “C _a -C _b haloalkyl” refers to a straight-chain or branched-chain hydrocarbon composed of _a to _b carbon atoms 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 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, 1,1-difluoroethyl, 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-1,1,1,2-trifluoroethyl, pentafluoroethyl, 2,2-difluoropropyl, 3,3,3-trifluoro Propyl, 3-bromo-3,3-difluoropropyl, 2,2,3,3-tetrafluoropropyl, 2,2,3,3,3-pentafluoroprop Ropyl, 1,1,2,3,3,3-hexafluoropropyl, heptafluoropropyl, 2,2,2-trifluoro-1-methylethyl, 2,2,2-trifluoro-1- (trifluoro Methyl) ethyl, 1,2,2,2-tetrafluoro-1- (trifluoromethyl) ethyl, 2,2,2-trifluoro-1,1-dimethylethyl, 2,2,3,4,4, Specific examples include 4-hexafluorobutyl, 2,2,3,3,4,4,4-heptafluorobutyl, nonafluorobutyl and the like, which are selected within the range of each specified number of carbon atoms.

The notation “C _a -C _b cycloalkyl” represents a cyclic hydrocarbon having a number of carbon atoms of _a to _{b, and} may form a monocyclic or complex cyclic structure having 3 to 10 membered rings. I can do it. Also, each ring may be optionally substituted by alkyl within the specified number of carbon atoms. Specific examples include cyclopropyl, cyclobutyl, 1-methylcyclopropyl, 2-methylcyclopropyl, cyclopentyl, 2,2-dimethylcyclopropyl, 1-methylcyclobutyl, cyclohexyl, etc. Is selected in the range.

The notation “C _a -C _b halocycloalkyl” refers to a cyclic hydrocarbon having from _a to _b carbon atoms in which a hydrogen atom bonded to a carbon atom is arbitrarily substituted by a halogen atom, and has three members. A monocyclic or composite ring structure from a ring to a 10-membered ring can be formed. Each ring may be arbitrarily substituted with alkyl within the range of the specified number of carbon atoms, and the substitution with a halogen atom may be a ring structure part, a side chain part, or both. And when substituted by two or more halogen atoms, the halogen atoms may be the same as each other or different from each other. For example, 1-fluorocyclopropyl, 1-chlorocyclopropyl, 2-chlorocyclopropyl, 2,2-difluorocyclopropyl, 2,2-dichlorocyclopropyl, 2,2-dibromocyclopropyl, 2,2-difluoro-1 -Methylcyclopropyl, 2,2-dichloro-1-methylcyclopropyl, 2,2-dibromo-1-methylcyclopropyl, 3-fluorocyclobutyl, 2,2,3,3-tetrafluorocyclobutyl, 1- Specific examples include fluorocyclopentyl, 1-chloro-2,2-dimethylcyclopropyl, 1-fluorocyclohexyl and the like, which are selected within the range of the specified number of carbon atoms.

The notation “C _a -C _b alkenyl” refers to an unsaturated carbon having a straight or branched chain having ab carbon atoms and having one or more double bonds in the molecule. Stands for hydrogen, for example vinyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 2-methyl-2-propenyl , 3-methyl-3-butenyl and the like are mentioned as specific examples, and each is selected within the range of the specified number of carbon atoms.

The notation of “C _a -C _b haloalkenyl” is a straight-chain or branched-chain consisting of _a to _b carbon atoms in which a hydrogen atom bonded to a carbon atom is arbitrarily substituted by a halogen atom, and Represents an unsaturated hydrocarbon having one or more double bonds in the molecule. At this time, when substituted by two or more halogen atoms, those halogen atoms may be the same or different from each other. For example, 2-fluorovinyl, 2-chlorovinyl, 1,2-dichlorovinyl, 2,2-dichlorovinyl, 2,2-dibromovinyl, 2-fluoro-2-propenyl, 2-chloro-2-propenyl, 3- Chloro-2-propenyl, 3,3-difluoro-2-propenyl, 2,3-dichloro-2-propenyl, 3,3-dichloro-2-propenyl, 2,3,3-trifluoro-2-propenyl, 2 , 3,3-Trichloro-2-propenyl, 1- (trifluoromethyl) ethenyl, 4,4-difluoro-3-butenyl, 3,4,4-trifluoro-3-butenyl, 2,4,4,4 -Tetrafluoro-2-butenyl, 3-chloro-4,4,4-trifluoro-2-butenyl and the like are mentioned as specific examples, and each is selected within the range of the specified number of carbon atoms.

The notation “C _a -C _b cycloalkenyl” represents an unsaturated hydrocarbon having a carbon number of ab and having one or two or more double bonds, and represents a three-membered ring. A monocyclic or composite ring structure of up to 10 members can be formed. Also, each ring may be optionally substituted by alkyl within the specified number of carbon atoms, and the double bond may be in either endo- or exo-form. For example, 1-cyclopentenyl, 2-cyclopentenyl, 1-cyclohexenyl, 2-cyclohexenyl, bicyclo [2.2.1] -5-hepten-2-yl and the like are mentioned as specific examples. It is selected within the range of the number of atoms.

The notation of “C _a -C _b halocycloalkenyl” is a ring composed of _a to _b carbon atoms in which a hydrogen atom bonded to a carbon atom is arbitrarily substituted by a halogen atom, and one or more in the molecule. Represents an unsaturated hydrocarbon having two or more double bonds, and can form a monocyclic or composite ring structure of three to ten membered rings. Also, each ring may be optionally substituted by alkyl within the specified number of carbon atoms, and the double bond may be in either endo- or exo-form. At this time, when substituted by two or more halogen atoms, those halogen atoms may be the same or different from each other. For example, 2-chloro-1-cyclobutenyl, 2-bromo-1-cyclopentenyl and the like are mentioned as specific examples, and each is selected within the range of the specified number of carbon atoms.

The notation of “C _a -C _b alkynyl” is an unsaturated hydrocarbon having a straight or branched chain of a and _b carbon atoms and having one or more triple bonds in the molecule. Represents, for example, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 1-hexynyl, 3-hexynyl, Specific examples include 3-methyl-1-pentynyl, 4-methyl-1-pentynyl, 3,3-dimethyl-1-butynyl and the like, which are selected within the range of the specified number of carbon atoms.

The notation of “C _a -C _b haloalkynyl” is a straight-chain or branched-chain consisting of _a to _b carbon atoms in which a hydrogen atom bonded to a carbon atom is optionally substituted by a halogen atom, and Represents an unsaturated hydrocarbon having one or more triple bonds in the molecule. At this time, when substituted by two or more halogen atoms, those halogen atoms may be the same or different from each other. For example, 2-chloroethynyl, 2-bromoethynyl, 2-iodoethynyl, 3-fluoro-1-propynyl, 3-chloro-1-propynyl, 3-chloro-2-propynyl, 3-bromo-1-propynyl, 3- Bromo-2-propynyl, 3-iodo-2-propynyl, 3,3-difluoro-1-propynyl, 3,3,3-trifluoro-1-propynyl, 3-bromo-1-butynyl and the like are specific examples. And each is selected within a specified number of carbon atoms.

The notation of "C _a -C _b alkoxy" represents alkyl-O- as defined above, wherein the number of carbon atoms is _{a- b} , and examples thereof include methoxy, ethoxy, n-propyloxy, i-propyloxy, n Specific examples include -butyloxy, i-butyloxy, sec-butyloxy, tert-butyloxy, pentyloxy, hexyloxy and the like, which are selected within the range of the specified number of carbon atoms.

The notation of “C _a -C _b haloalkoxy” represents haloalkyl-O— having the above-mentioned meaning having from _a to _b carbon atoms, and is, for example, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy. 2,2-fluoroethoxy, 2-chloroethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2-chloro-1,1,2-trifluoroethoxy, 1, 1,2,3,3,3-hexafluoropropyloxy and the like are mentioned as specific examples, and each is selected within the range of the specified number of carbon atoms.

The notation of "C _a -C _b alkenyloxy" represents alkenyl-O- as defined above, wherein the number of carbon atoms is _{a- b} , and is, for example, 2-propenyloxy, 2-butenyloxy, 1-methyl-2. -Propenyloxy, 2-methyl-2-propenyloxy, 3-methyl-2-butenyloxy, 1,1-dimethyl-2-propenyloxy and the like are specific examples, and each is selected within the range of the specified number of carbon atoms. Is done.

The notation "C _a -C _b haloalkenyloxy" represents haloalkenyl-O- as defined above, which has from _a to _b carbon atoms, and is, for example, 2-fluoro-2-propenyloxy, 2-chloro. -2-propenyloxy, 3-chloro-2-propenyloxy, 3,3-difluoro-2-propenyloxy, 2,3-dichloro-2-propenyloxy, 3,3-dichloro-2-propenyloxy, 2, Specific examples include 3,3-trifluoro-2-propenyloxy and the like, which are selected within the range of the specified number of carbon atoms.

The notation "C _a -C _b alkynyloxy" represents alkynyl-O- in the above meaning having from _a to _b carbon atoms, for example, 2-propynyloxy, 2-butynyloxy, 1-methyl-2. -Propynyloxy, 1,1-dimethyl-2-propynyloxy and the like are mentioned as specific examples, and each is selected within the range of the specified number of carbon atoms.

The notation "C _a -C _b haloalkynyloxy" represents haloalkynyl-O- as defined above, wherein the number of carbon atoms is ab, and is, for example, 3-chloro-2-propynyloxy, 3-bromo. Specific examples include -2-propynyloxy, 3-iodo-2-propynyloxy and the like, which are selected within the range of each specified number of carbon atoms.

The notation of "C _a -C _b alkylthio" represents alkyl-S- having the above-mentioned meaning having from _a to _b carbon atoms, and includes, for example, methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio. , I-butylthio, sec-butylthio, tert-butylthio and the like are mentioned as specific examples, and each is selected within the range of the specified number of carbon atoms.

The notation of `` C _a -C _b alkylsulfinyl '' represents alkyl-S (O)-having the above-mentioned meaning having from _a to _b carbon atoms, and includes, for example, methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, Specific examples include i-propylsulfinyl and the like, which are selected within the range of each specified number of carbon atoms.

The notation of “C _a -C _b alkylsulfonyl” represents alkyl-SO ₂ — having the above meaning having from _a to _b carbon atoms, and includes, for example, methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, i- Propylsulfonyl and the like are mentioned as specific examples, and each is selected within the range of the specified number of carbon atoms.

The notation of "C _a -C _b haloalkylthio" represents haloalkyl-S- as defined above, which has a carbon number of _a to _{b, and} includes, for example, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, trichloromethylthio, Bromodifluoromethylthio, 2,2,2-trifluoroethylthio, 1,1,2,2-tetrafluoroethylthio, 2-chloro-1,1,2-trifluoroethylthio, pentafluoroethylthio, Specific examples include 1,2,3,3,3-hexafluoropropylthio, heptafluoropropylthio, 1,2,2,2-tetrafluoro-1- (trifluoromethyl) ethylthio, nonafluorobutylthio and the like. And each is selected within a specified number of carbon atoms.

The notation of "C _a -C _b haloalkylsulfinyl" represents haloalkyl-S (O)-having the above-mentioned meaning having from _a to _b carbon atoms, and specific examples thereof include difluoromethylsulfinyl and trifluoromethylsulfinyl. By way of example, each is selected in a specified number of carbon atoms.

The notation of “C _a -C _b haloalkylsulfonyl” represents haloalkyl-SO ₂ — having the above-mentioned meaning having from _a to _b carbon atoms, and specific examples thereof include difluoromethylsulfonyl and trifluoromethylsulfonyl. And are selected within the range of each specified number of carbon atoms.

The notation of `` di (C _a -C _b alkyl) amino '' is defined as an alkyl having the above meaning in which both hydrogen atoms are the same or different from each other, and the number of carbon atoms is a to b. It represents a substituted amino group and includes, for example, dimethylamino, ethyl (methyl) amino, diethylamino, di (n-propyl) amino and the like as specific examples, each being selected within the range of the specified number of carbon atoms.

The notation of "C _a -C _b alkoxyamino" represents alkyl-ONH- having the above-mentioned meaning having from _a to _b carbon atoms, and includes, for example, methoxyamino, ethoxyamino, n-propyloxyamino, i- Specific examples include propyloxyamino, n-butyloxyamino, i-butyloxyamino, sec-butyloxyamino, tert-butyloxyamino and the like, which are selected within the range of each specified number of carbon atoms.

The notation of “tri (C _a -C _b alkyl) silyl” represents a silyl substituted by an alkyl having the above-mentioned meaning consisting of _a to _b carbon atoms which may be the same or different from each other. For example, trimethylsilyl, triethylsilyl, tri (n-propyl) silyl, ethyldimethylsilyl, n-propyldimethylsilyl, n-butyldimethylsilyl, i-butyldimethylsilyl, tert-butyldimethylsilyl and the like are specific examples. Each is selected within a specified range of carbon atoms.

The notation of "C _a -C _b alkylcarbonyl" represents alkyl-C (O)-having the above-mentioned meaning having from _a to _b carbon atoms, and includes, for example, acetyl, propionyl, butyryl, isobutyryl, valeryl, isovaleryl. Specific examples include 2,2-methylbutanoyl, pivaloyl, and the like, which are selected within the range of each specified number of carbon atoms.

The notation of “C _a -C _b cycloalkylcarbonyl” represents cycloalkyl-C (O) — having the above meaning having from _a to _b carbon atoms, and includes, for example, cyclopropylcarbonyl, cyclobutylcarbonyl, Specific examples include -methylcyclopropylcarbonyl, 2-methylcyclopropylcarbonyl, cyclopentylcarbonyl, 2,2-dimethylcyclopropylcarbonyl, cyclohexylcarbonyl and the like, which are selected within the range of the specified number of carbon atoms.

The notation of "C _a -C _b alkoxycarbonyl" represents alkyl-OC (O)-having the above-mentioned meaning having from _a to _b carbon atoms, such as methoxycarbonyl, ethoxycarbonyl, and n-propyloxycarbonyl. , I-propyloxycarbonyl, n-butoxycarbonyl, i-butoxycarbonyl, tert-butoxycarbonyl, and the like, as specific examples, each being selected within the range of the specified number of carbon atoms.

“Cyano (C _d -C _e ) alkyl”, “C _a -C _b alkoxymethyl”, “C _a -C _b alkoxy (C _d -C _e ) alkyl”, “C _a -C _b haloalkoxy (C _d) -C _e) alkyl "," _C a -C _b alkylthio _(C d ~C _e) alkyl "," _C a -C _b alkylsulfinyl _(C d ~C _e) alkyl "," _C a -C _b alkylsulfonyl (C _d -C _e ) alkyl ”,“ C _a -C _b haloalkylthio (C _d -C _e ) alkyl ”,“ C _a -C _b haloalkylsulfinyl (C _d -C _e ) alkyl ”,“ C _a -C C _b haloalkylsulfonyl (C _d ~C _e) alkyl ", notation" phenyl (C _d ~C _e) alkyl "or" (Z) phenyl (C _d ~C _e) alkyl substituted by _m ', respectively Any cyano, C _a -C _b alkoxy, C _a -C _b haloalkoxy, C _a -C as defined above _b alkylthio, C _a -C _b alkylsulfinyl, C _a -C _b alkylsulfonyl, C _a -C _b haloalkylthio, C _a -C _b haloalkylsulfinyl, C _a -C _b haloalkylsulfonyl, by phenyl or _{(Z) m} A hydrogen atom bonded to a carbon atom by a substituted phenyl represents methyl optionally substituted or an alkyl having the above-mentioned meaning having d to e carbon atoms, and within the range of each specified number of carbon atoms. Selected.

The notation of “(C _a -C _b ) alkyl substituted by R ⁷ ” means the above-mentioned meaning consisting of _a to _b carbon atoms in which a hydrogen atom bonded to a carbon atom is substituted by any R ⁷ . And is selected within the range of each specified number of carbon atoms.

Designation "optionally substituted by R ⁹ (C _a ~C _b) alkyl", by any R ^9, carbon atoms in which the hydrogen atoms bonded to carbon atom is optionally substituted from a~b pieces Which represents alkyl as defined above, and is selected within the range of each specified number of carbon atoms. At this time, when there are two or more substituents R ⁹ on each (C _a -C _b ) alkyl, each R ⁹ may be the same or different from each other.

_"C a -C _b cycloalkyl _(C d -C _e) cycloalkyl, hydroxy _(C d -C _e) cycloalkyl", _"C a -C _b alkoxy _(C d -C _e) cycloalkyl" or phenyl ( The notation of C _d -C _e ) cycloalkyl refers to a carbon atom by any C _a -C _b cycloalkyl, hydroxyl group, as defined above, or any C _a -C _b alkoxy or phenyl as defined above. The bonded hydrogen atom is a cycloalkyl having the above-mentioned meaning in which the number of carbon atoms substituted is from d to e, and is selected within the range of each specified number of carbon atoms.

Notation "cyano (C _a ~C _b) alkoxy", "phenyl (C _a ~C _b) alkoxy" or "phenyl substituted by _{(Z) m (C a ~C} b) alkoxy", cyano, phenyl Or a phenyl substituted by (Z) _m represents an alkoxy as defined above wherein the number of carbon atoms replaced by a hydrogen atom bonded to a carbon atom is a to b, and each of the designated number of carbon atoms Selected by range.

"R ¹ and R ² together form a C ₂ -C ₅ alkylene chain to form a 3- to 6-membered ring with the carbon atom to which R ¹ and R ² are attached, May contain one or two oxygen atoms, sulfur atoms or nitrogen atoms, and specific examples of the notation include, for example, cyclopropane, oxirane, thiirane, aziridine, cyclobutane, oxetane, thietane, azetidine, cyclopentane, oxolane, thiolane , Pyrrolidine, dioxolane, dithiolane, cyclohexane, tetrahydropyran, tetrahydrothiopyran, piperidine, 1,3-dioxane, 1,3-dithiane and the like, and each is selected within the range of the specified number of atoms.

"R ¹⁶ and R ¹⁷ may together form a C ₂ -C ₅ alkylene chain to form a 3- to 6-membered ring with the nitrogen atom to which R ¹⁶ and R ¹⁷ are attached. In this case, the alkylene chain may contain one oxygen atom or one sulfur atom, and examples thereof include: aziridine, azetidine, pyrrolidine, oxazolidine, thiazolidine, piperidine, 2H-3,4,5,6 -Tetrahydro-1,3-oxazine, morpholine, 2H-3,4,5,6-tetrahydro-1,3-thiazine, thiomorpholine and the like, each being selected within the range of the specified number of atoms.

In the compounds included in the present invention, a preferred range of the substituent of G ^1, include the following groups.

^{That, G 1 -I: G 1 -1} [ wherein, X ¹ represents a trifluoromethyl, X ² represents a hydrogen atom. ].

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

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

G ¹ -IV: G ¹ -4 [wherein, X ¹ is a halogen atom or trifluoromethyl. ].

G ¹ -V: G ¹ -5 and G ¹ -6 [where X ¹ represents a halogen atom, methyl or trifluoromethyl. ].

G ¹ -VI: G ¹ -7 [where X ¹ represents trifluoromethyl and r represents 0. ].

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

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

G ¹ -IX: G ^1-2 and G ^1-3 [where X ¹ represents methyl, methylthio, trifluoromethylthio, methylsulfinyl, difluoromethylsulfonyl or trifluoromethylsulfonyl. ].

G ¹ -X: G ¹ -4 [where X ¹ represents methyl or difluoromethyl. ].

G ¹ -XI: G ¹ -5 and G ¹ -6 [where X ¹ represents difluoromethyl. ].

G ¹ -XII: G ¹ -7 [where X ¹ represents methyl or trifluoromethyl, and r represents 0, 1 or 2. ].

Among these, more preferably ^{G 1 -I~G 1 -VI, G 1} -IX and ^{G 1} -X is a range of the substituent represented by G ^1, further, G ¹ -I, G ¹ -III , G ¹ -IV, G ¹ -IX and G ¹ -X are particularly preferred.

In the compounds included in the present invention, as a combination of the preferred range of the substituent represented by Y ¹ and Y ^2, include the following groups YI~Y-IV.

That, YI: Y ¹ is a halogen atom, and ^{Y 2} is a hydrogen atom.

Y-II: Y ¹ is a halogen atom, and Y ² is a fluorine atom or a chlorine atom.

Y-III: Y ¹ is methyl or methoxy, and Y ² is a hydrogen atom.

Y-IV: Y ¹ and ^{Y 2} are simultaneously methyl.

Of these, more preferable YI and Y-II is a combination of substituents represented by Y ¹ and Y ^2, further, YI is particularly preferred.

In the compounds encompassed by the present invention, examples of preferred combinations of the substituents represented by R ¹ , R ² , R ³ and R ⁴ include the following groups RI to R-XIII.

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

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

R-III: R ¹ is methoxy, R ² is a hydrogen atom, R ³ is a hydrogen atom and methyl, and R ⁴ is a hydrogen atom.

R-IV: R ¹ is a fluorine atom, methyl, ethyl, ethoxy, trifluoroethoxy, allyloxy, propargyloxy, benzyloxy and methylthio, R ² is a hydrogen atom, R ³ is a hydrogen atom and methyl, and R ⁴ is a hydrogen atom .

RV: R ¹ and R ² are fluorine atoms, R ³ is ethyl, and R ⁴ is a hydrogen atom.

R-VI: R ¹ is a fluorine atom and methyl, R ² is methyl, R ³ is a hydrogen atom and methyl, and R ⁴ is a hydrogen atom.

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

R-VIII: R ¹ and R ² are hydrogen atoms, R ³ is C ₁ -C ₃ alkyl and C ₁ -C ₃ haloalkyl, and R ⁴ is a hydrogen atom and C ₁ -C ₃ alkyl.

R-IX: R ¹ and R ² are hydrogen atoms, and R ³ and R ⁴ together form an ethylene chain, forming a cyclopropyl ring with the carbon atoms to which R ³ and R ⁴ are attached.

RX: R ¹ is phenylmethyl substituted by C ₁ -C ₃ alkyl, C ₁ -C ₃ haloalkyl, benzyl, (Z) _m [where Z is a halogen atom, cyano, nitro, methyl, trifluoromethyl, Methoxy, difluoromethoxy, trifluoromethoxy, methylthio, methylsulfinyl, methylsulfonyl, difluoromethylthio, difluoromethylsulfonyl, trifluoromethylthio or trifluoromethylsulfonyl, m represents 1 or 2, and m represents 2. In the formula, each Z may be the same or different from each other. And cyclopropyl, R ² is a hydrogen atom, R ³ is a hydrogen atom and methyl, and R ⁴ is a hydrogen atom.

R-XI: R ¹ is substituted by C ₁ -C ₃ alkoxy, C ₁ -C ₃ haloalkoxy, C ₃ -C ₄ alkenyloxy, C ₃ -C ₄ alkynyloxy, cyanomethoxy, benzyloxy, (Z) _m Phenylmethoxy [where Z is a halogen atom, cyano, nitro, methyl, trifluoromethyl, methoxy, difluoromethoxy, trifluoromethoxy, methylthio, methylsulfinyl, methylsulfonyl, difluoromethylthio, difluoromethylsulfonyl, trifluoromethylthio Or trifluoromethylsulfonyl, m represents 1 or 2, and when m represents 2, each Z may be the same or different from each other. ], C ₁ -C ₃ alkylthio and _C 1 -C ₃ haloalkylthio, R ² is a hydrogen atom, R ³ is a hydrogen atom and methyl, and ^{R 4} is a hydrogen atom.

R-XII: R ¹ and R ² are fluorine atoms, and R ³ and R ⁴ are methyl.

R-XIII: R ¹ is C ₁ -C ₃ alkyl, R ² is a fluorine atom and methyl, R ³ is a hydrogen atom and methyl, and R ⁴ is a hydrogen atom.

Of these, RI to R-VII and R-XII are more preferable as the combination of the ranges of the substituents represented by R ¹ , R ² , R ³ and R ⁴ , and furthermore, RI to R-III and R -VII is particularly preferred.

In the compounds included in the present invention, preferred ranges of the substituent represented by R ⁵ include, for example, the following groups.

That is, R ⁵ -I: a hydrogen atom.

R ⁵ -II: C ₁ ~C ₄ alkyl.

R ⁵ -III: substituted by R ⁸ _(C 1 _{~C 2)} alkyl [wherein, R ⁸ represents cyano, a C ₃ -C ₆ cycloalkyl or -OR ^14, R ¹⁴ is _C 1 -C ₄ Represents alkyl. ].

R ⁵ -IV: cyclopropyl.

R ⁵ -V: C ₂ ~C ₄ alkenyl and _C 3 -C ₄ alkynyl.

R ⁵ -VI: C ₁ ~C ₄ haloalkylthio.

^{R 5 -VII: -C (O)} R 9 [ wherein, R ⁹ represents _C 1 -C ₄ alkyl. ] And _C 1 -C ₄ alkoxycarbonyl.

R ⁵ -VIII: substituted by R ⁸ _(C 1 _{~C 2)} alkyl [wherein, R ⁸ is -OR ^14, C ₁ ~C ₄ alkylthio, -C (O) NH ₂ or -C (S) represents NH _2, R ¹⁴ represents a _C 2 -C ₄ haloalkyl. ].

R ⁵ -IX: C ₃ ~C ₆ cycloalkyl.

R ⁵ -X: C ₁ ~C ₄ alkoxy.

R ⁵ -XI: —C (O) R ⁹ [where R ⁹ represents C ₃ -C ₄ cycloalkyl. ].

Of these, more preferred ^{R 5 -I~R 5} -VIII and ^{R 5} -XI as range of the substituent of R ^5, further, R ⁵ -I~R ⁵ -III and ^{R 5} -V ~R ⁵ -VII is particularly preferred.

In the compounds included in the present invention, preferred ranges of the substituent represented by R ⁶ include, for example, the following groups.

That is, R ⁶ -I: C ₃ -C ₆ cycloalkyl.

R ⁶ -II: phenyl substituted by (Z) _m [where Z represents a halogen atom, and when m represents 2 or 3, each Z may be the same or different from each other. M represents 1, 2 or 3. ].

R ⁶ -III: D-1, D-2, D-6, D-23 and D-25 [where Z represents a halogen atom or trifluoromethyl, and when n represents 2, each represents Z may be the same as or different from each other, and when two Zs are adjacent, the two adjacent Zs are each formed by forming -CH = CHCH = CH-. A 6-membered ring may be formed together with the carbon atom to which Z is bonded, R ¹² represents C ₁ -C ₄ alkyl, and n represents 0, 1 or 2. ].

R ⁶ -IV: a hydrogen atom, a halogen atom, C ₁ -C ₄ alkyl and C ₁ -C ₄ haloalkyl.

R ⁶ -V: optionally substituted by R ⁹ _(C 1 ~C ₄₎ alkyl [wherein, R ⁹ represents -OR ¹⁴ or ^{_{-S (O) r R 15,}} R 14 is a hydrogen atom, methyl , Ethyl or C ₁ -C ₂ haloalkyl, R ¹⁵ represents methyl, ethyl or C ₁ -C ₂ haloalkyl, and r represents 0, 1 or 2. ], Hydroxy _(C 3 -C ₆₎ cycloalkyl, C ₁ -C ₂ alkoxy _(C 3 -C ₆₎ cycloalkyl, C ₄ -C ₆ cycloalkenyl, tri _(C 1 -C ₄ alkyl) silyl and -C (R ¹⁰ ) = NOR ¹¹ [where R ¹⁰ represents a hydrogen atom or methyl, and R ¹¹ represents methyl or ethyl. ].

R _⁶ -VI: C ₃ ~C ⁶ halocycloalkyl.

R ⁶ -VII: phenyl and phenyl substituted by (Z) _m wherein 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 alkylsulfonyl, C ₁ -C ₄ haloalkylthio, C ₁ -C ₄ haloalkylsulfinyl or _C 1 ~ It represents C ₄ haloalkylsulfonyl, when m represents 2, 3, 4 or 5, each Z may be the even or different from each other the same as each other, further, when two Z are adjacent The two adjacent Zs may form a 6-membered ring together with the carbon atom to which each Z is attached by forming -CH = CHCH = CH-, wherein each of the Hydrogen atoms bonded to carbon atoms are halo It may be optionally substituted by a gen atom, methyl or trifluoromethyl, and m represents 1, 2, 3, 4 or 5. ].

R ⁶ -VIII: phenyl substituted by (Z) _m , wherein m represents 2 or 3, at least two Zs are in adjacent positions, and two adjacent Zs together are —CH _{2 CH 2 CH 2 -, - CH} 2 CH 2 O -, - OCH 2 O -, - OCH 2 CH 2 O -, - OCH = CH -, - SCH = CH -, - N (R 12) CH = CH- , -OCH = N -, - SCH = N -, - N (R 12) CH = N -, - ON = CH -, - SN = CH -, - N (R 12) N = CH -, - N ( R ¹² ) N = N-, = NN (R ¹² ) CH =, = NON = or = NSN = to form a 5- or 6-membered ring with the carbon atom to which each Z is attached, At this time, the hydrogen atom bonded to each carbon atom forming the ring may be optionally substituted by a halogen atom, methyl or trifluoromethyl, and R ¹² is C ₁ -C ₄ alkyl or C ₁ -C ₄ When m represents 3, the remaining Z is a halogen atom, cyano, methyl, trifluoromethyl, methoxy It represents a difluoromethoxy or trifluoromethoxy. ].

R ⁶ -IX: phenyl substituted by (Z) _m , wherein m represents 2, 3, 4 or 5, at least two Z are in adjacent positions and two adjacent Z are taken together -CH ₂ CH ₂ CH ₂ Te _{-, - CH 2 CH 2 O} -, - CH 2 OCH 2 -, - OCH 2 O -, - CH 2 CH 2 S (O) r -, - CH 2 CH 2 CH 2 CH _2- , -CH ₂ CH ₂ CH ₂ O-, -CH ₂ CH ₂ OCH _2- , -CH ₂ OCH ₂ O-, -OCH ₂ CH ₂ O-, -CH ₂ CH ₂ CH ₂ S (O) _{r -, - OCH = CH -} , - SCH = CH -, - N (R 12) CH = CH -, - OCH = N -, - SCH = N -, - N (R 12) CH = N -, - ON = CH -, - SN = CH -, - N (R 12) N = CH -, - SN = N -, - N (R 12) N = N -, = NN (R 12) CH =, = NON =, = NSN =, -N = CHCH = CH-, -CH = NCH = CH-, -N = NCH = CH-, -N = CHN = CH-, -N = CHCH = N-, -CH = NN = CH- or -N = NCH = N- to form a 5- or 6-membered ring together with the carbon atom to which each Z is bonded, and then bond to each carbon atom forming the ring Hydrogen atom is a halogen atom, Or may be optionally substituted by trifluoromethyl, R ¹² represents a C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl, when m represents 3, 4 or 5, the remaining Z halogen atom , Cyano, methyl, trifluoromethyl, methoxy, difluoromethoxy or trifluoromethoxy, and r represents 0, 1 or 2. ].

R ⁶ -X: D-1, D-2, D-6, D-8, D-23 and D-25 [where Z represents a halogen atom, C ₁ -C ₄ alkyl or trifluoromethyl, When n represents 2 or 3, each Z may be the same as or different from each other, and when two Zs are adjacent, the two adjacent Zs may be -CH By forming = CHCH = CH-, each Z may form a 6-membered ring with the carbon atom to which each Z is attached, wherein R ¹² represents C ₁ -C ₄ alkyl and n is 0, 1, 2, or 3 is represented. ].

R ⁶ -XI: D-1, D-2, D-6, D-8, D-23, D-24, D-25 and D-26 [where Z is a halogen atom, cyano, nitro, C _{When 1 to} C ₄ alkyl, C _{1 to} C ₄ haloalkyl, C _{1 to} C ₄ alkoxy or C _{1 to} C ₄ alkylsulfonyl, and n represents 2, 3 or 4, each Z is the same as each other. may be the or different from each other there, further, when two Z are adjacent, the two adjacent Z is _{-CH 2 CH 2 CH 2 -,} - CH 2 CH 2 O -, - CH 2 CH ₂ CH ₂ CH _2- , -CH ₂ CH ₂ CH ₂ O-, -OCH ₂ CH ₂ O-, -CH ₂ CH ₂ S (O) _r CH _2- , -OCH = CH-, -SCH = CH ^{-, - N (R 12)} CH = CH -, - OCH = N -, - SCH = N -, - N (R 12) CH = N -, - N (R 12) N = CH -, - N ( R ¹² ) forming N = N-, -CH = CHCH = CH-, -N = CHCH = CH-, -CH = NCH = CH-, -N = CHN = CH- or -N = CHCH = N- This may form a 5- or 6-membered ring with the carbon atom to which each Z is attached, Hydrogen atoms bonded to each carbon atom forming the ring is a halogen atom, methyl, may be optionally substituted by trifluoromethyl or methoxy, R ¹² is C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl And n represents 0, 1, 2, 3 or 4, and r represents 0, 1 or 2. ].

Among these, more preferably ^{R 6 -I~R 6 -III, R 6} -V and ^{R 6 -VII~R 6} -XI as range of the substituent of R ^6, further, R ⁶ -III , R ⁶ -VIII and R ⁶ -X are particularly preferred.

  Each group showing the preferable range of each substituent in the compounds included in the present invention can be arbitrarily combined, and each represents a preferable range of the compound of the present invention.

Examples of preferred ranges of G ¹ , R ^{1 to} R ⁴ (represented by RI to R-XIII) and R ⁶ of the compound represented by the formula (I) include, for example, the combinations shown in Table 1 below. Is mentioned. However, the combinations in Table 1 are for illustration only, and the compounds of the present invention represented by the formula (I) are not limited thereto.
Table 1 Table 1 (continued)
―――――――――――――――― ――――――――――――――――
G ¹ R ^{1 to} R ⁴ R ⁶ G ¹ R ^{1 to} R ⁴ R ⁶
―――――――――――――――― ――――――――――――――――
G ¹ -I RI R ⁶ -IG ¹ -IV RI R ⁶ -VI
G ¹ -I RI R ⁶ -II G ¹ -IV RI R ⁶ -VII
G ¹ -I RI R ⁶ -III G ¹ -IV RI R ⁶ -VIII
G ¹ -I RI R ⁶ -IV G ¹ -IV RI R ⁶ -IX
G ¹ -I RI R ⁶ -VG ¹ -IV RI R ⁶ -X
G ¹ -I RI R ⁶ -VI G ¹ -IV RI R ⁶ -XI
G ¹ -I RI R ⁶ -VII G ¹ -IV R-II R ⁶ -I
G ¹ -I RI R ⁶ -VIII G ¹ -IV R-II R ⁶ -II
G ¹ -I RI R ⁶ -IX G ¹ -IV R-II R ⁶ -III
G ¹ -I RI R ⁶ -XG ¹ -IV R-II R ⁶ -IV
G ¹ -I RI R ⁶ -XI G ¹ -IV R-II R ⁶ -V
G ¹ -I R-II R ⁶ -IG ¹ -IV R-II R ⁶ -VI
G ¹ -I R-II R ⁶ -II G ¹ -IV R-II R ⁶ -VII
G ¹ -I R-II R ⁶ -III G ¹ -IV R-II R ⁶ -VIII
G ¹ -I R-II R ⁶ -IV G ¹ -IV R-II R ⁶ -IX
G ¹ -I R-II R ⁶ -VG ¹ -IV R-II R ⁶ -X
G ¹ -I R-II R ⁶ -VI G ¹ -IV R-II R ⁶ -XI
G ¹ -I R-II R ⁶ -VII G ¹ -IV R-III R ⁶ -I
G ¹ -I R-II R ⁶ -VIII G ¹ -IV R-III R ⁶ -II
G ¹ -I R-II R ⁶ -IX G ¹ -IV R-III R ⁶ -III
G ¹ -I R-II R ⁶ -XG ¹ -IV R-III R ⁶ -IV
G ¹ -I R-II R ⁶ -XI G ¹ -IV R-III R ⁶ -V
G ¹ -I R-III R ⁶ -IG ¹ -IV R-III R ⁶ -VI
G ¹ -I R-III R ⁶ -II G ¹ -IV R-III R ⁶ -VII
G ¹ -I R-III R ⁶ -III G ¹ -IV R-III R ⁶ -VIII
G ¹ -I R-III R ⁶ -IV G ¹ -IV R-III R ⁶ -IX
G ¹ -I R-III R ⁶ -VG ¹ -IV R-III R ⁶ -X
G ¹ -I R-III R ⁶ -VI G ¹ -IV R-III R ⁶ -XI
G ¹ -I R-III R ⁶ -VII G ¹ -IV R-IV R ⁶ -I
G ¹ -I R-III R ⁶ -VIII G ¹ -IV R-IV R ⁶ -II
G ¹ -I R-III R ⁶ -IX G ¹ -IV R-IV R ⁶ -III
G ¹ -I R-III R ⁶ -XG ¹ -IV R-IV R ⁶ -VIII
G ¹ -I R-III R ⁶ -XI G ¹ -IV R-IV R ⁶ -IX
G ¹ -I R-IV R ⁶ -IG ¹ -IV R-IV R ⁶ -X
G ¹ -I R-IV R ⁶ -II G ¹ -IV R-IV R ⁶ -XI
G ¹ -I R-IV R ⁶ -III G ¹ -IV RV R ⁶ -III
G ¹ -I R-IV R ⁶ -VIII G ¹ -IV RV R ⁶ -VIII
G ¹ -I R-IV R ⁶ -IX G ¹ -IV RV R ⁶ -X
G ¹ -I R-IV R ⁶ -XG ¹ -IV R-VI R ⁶ -III
G ¹ -I R-IV R ⁶ -XI G ¹ -IV R-VI R ⁶ -VIII
G ¹ -I RV R ⁶ -III G ¹ -IV R-VI R ⁶ -X
G ¹ -I RV R ⁶ -VIII G ¹ -IV R-VII R ⁶ -I
G ¹ -I RV R ⁶ -XG ¹ -IV R-VII R ⁶ -II
G ¹ -I R-VI R ⁶ -III G ¹ -IV R-VII R ⁶ -III
G ¹ -I R-VI R ⁶ -VIII G ¹ -IV R-VII R ⁶ -IV
G ¹ -I R-VI R ⁶ -XG ¹ -IV R-VII R ⁶ -V
G ¹ -I R-VII R ⁶ -IG ¹ -IV R-VII R ⁶ -VI
G ¹ -I R-VII R ⁶ -II G ¹ -IV R-VII R ⁶ -VII
G ¹ -I R-VII R ⁶ -III G ¹ -IV R-VII R ⁶ -VIII
G ¹ -I R-VII R ⁶ -IV G ¹ -IV R-VII R ⁶ -IX
G ¹ -I R-VII R ⁶ -VG ¹ -IV R-VII R ⁶ -X
G ¹ -I R-VII R ⁶ -VI G ¹ -IV R-VII R ⁶ -XI
G ¹ -I R-VII R ⁶ -VII G ¹ -IV R-VIII R ⁶ -III
G ¹ -I R-VII R ⁶ -VIII G ¹ -IV R-VIII R ⁶ -VIII
G ¹ -I R-VII R ⁶ -IX G ¹ -IV R-VIII R ⁶ -X
G ¹ -I R-VII R ⁶ -XG ¹ -IV R-IX R ⁶ -III
G ¹ -I R-VII R ⁶ -XI G ¹ -IV R-IX R ⁶ -VIII
G ¹ -I R-VIII R ⁶ -III G ¹ -IV R-IX R ⁶ -X
G ¹ -I R-VIII R ⁶ -VIII G ¹ -IV RX R ⁶ -III
G ¹ -I R-VIII R ⁶ -XG ¹ -IV RX R ⁶ -VIII
G ¹ -I R-IX R ⁶ -III G ¹ -IV RX R ⁶ -X
G ¹ -I R-IX R ⁶ -VIII G ¹ -IV R-XI R ⁶ -III
G ¹ -I R-IX R ⁶ -XG ¹ -IV R-XI R ⁶ -VIII
G ¹ -I RX R ⁶ -III G ¹ -IV R-XI R ⁶ -X
G ¹ -I RX R ⁶ -VIII G ¹ -IV R-XII R ⁶ -III
G ¹ -I RX R ⁶ -XG ¹ -IV R-XII R ⁶ -VIII
G ¹ -I R-XI R ⁶ -III G ¹ -IV R-XII R ⁶ -X
G ¹ -I R-XI R ⁶ -VIII G ¹ -IV R-XIII R ⁶ -III
G ¹ -I R-XI R ⁶ -XG ¹ -IV R-XIII R ⁶ -VIII
G ¹ -I R-XII R ⁶ -III G ¹ -IV R-XIII R ⁶ -X
G ¹ -I R-XII R ⁶ -VIII G ¹ -V RI R ⁶ -I
G ¹ -I R-XII R ⁶ -XG ¹ -V RI R ⁶ -II
G ¹ -I R-XIII R ⁶ -III G ¹ -V RI R ⁶ -III
G ¹ -I R-XIII R ⁶ -VIII G ¹ -V RI R ⁶ -VIII
G ¹ -I R-XIII R ⁶ -XG ¹ -V RI R ⁶ -IX
G ¹ -II RI R ⁶ -IG ¹ -V RI R ⁶ -X
G ¹ -II RI R ⁶ -II G ¹ -V RI R ⁶ -XI
G ¹ -II RI R ⁶ -III G ¹ -V R-II R ⁶ -I
^{G 1 -II RI R 6 -VIII G} 1 -V R-II R 6 -II
G ¹ -II RI R ⁶ -XG ¹ -V R-II R ⁶ -III
G ¹ -II RI R ⁶ -XI G ¹ -V R-II R ⁶ -VIII
G ¹ -II R-II R ⁶ -IG ¹ -V R-II R ⁶ -IX
G ¹ -II R-II R ⁶ -II G ¹ -V R-II R ⁶ -X
G ¹ -II R-II R ⁶ -III G ¹ -V R-II R ⁶ -XI
G ¹ -II R-II R ⁶ -VIII G ¹ -V R-III R ⁶ -I
G ¹ -II R-II R ⁶ -XG ¹ -V R-III R ⁶ -II
G ¹ -II R-II R ⁶ -XI G ¹ -V R-III R ⁶ -III
G ¹ -II R-III R ⁶ -IG ¹ -V R-III R ⁶ -VIII
G ¹ -II R-III R ⁶ -II G ¹ -V R-III R ⁶ -IX
G ¹ -II R-III R ⁶ -III G ¹ -V R-III R ⁶ -X
G ¹ -II R-III R ⁶ -VIII G ¹ -V R-III R ⁶ -XI
G ¹ -II R-III R ⁶ -XG ¹ -V R-VII R ⁶ -I
G ¹ -II R-III R ⁶ -XI G ¹ -V R-VII R ⁶ -II
G ¹ -III RI R ⁶ -IG ¹ -V R-VII R ⁶ -III
G ¹ -III RI R ⁶ -II G ¹ -VR -VII R ⁶ -VIII
^{G 1 -III RI R 6 -III G} 1 -V R-VII R 6 -IX
G ¹ -III RI R ⁶ -IV G ¹ -V R-VII R ⁶ -X
G ¹ -III RI R ⁶ -VG ¹ -V R-VII R ⁶ -XI
G ¹ -III RI R ⁶ -VI G ¹ -VI RI R ⁶ -I
G ¹ -III RI R ⁶ -VII G ¹ -VI RI R ⁶ -II
G ¹ -III RI R ⁶ -III G ¹ -VI RI R ⁶ -III
G ¹ -III RI R ⁶ -IX G ¹ -VI RI R ⁶ -VIII
G ¹ -III RI R ⁶ -XG ¹ -VI RI R ⁶ -IX
G ¹ -III RI R ⁶ -XI G ¹ -VI RI R ⁶ -X
G ¹ -III R-II R ⁶ -IG ¹ -VI RI R ⁶ -XI
G ¹ -III R-II R ⁶ -II G ¹ -VI R-II R ⁶ -I
G ¹ -III R-II R ⁶ -III G ¹ -VI R-II R ⁶ -II
G ¹ -III R-II R ⁶ -IV G ¹ -VI R-II R ⁶ -III
G ¹ -III R-II R ⁶ -VG ¹ -VI R-II R ⁶ -VIII
G ¹ -III R-II R ⁶ -VI G ¹ -VI R-II R ⁶ -IX
G ¹ -III R-II R ⁶ -VII G ¹ -VI R-II R ⁶ -X
G ¹ -III R-II R ⁶ -VIII G ¹ -VI R-II R ⁶ -XI
G ¹ -III R-II R ⁶ -IX G ¹ -VI R-III R ⁶ -I
G ¹ -III R-II R ⁶ -XG ¹ -VI R-III R ⁶ -II
G ¹ -III R-II R ⁶ -XI G ¹ -VI R-III R ⁶ -III
G ¹ -III R-III R ⁶ -IG ¹ -VI R-III R ⁶ -VIII
G ¹ -III R-III R ⁶ -II G ¹ -VI R-III R ⁶ -IX
G ¹ -III R-III R ⁶ -III G ¹ -VI R-III R ⁶ -X
G ¹ -III R-III R ⁶ -IV G ¹ -VI R-III R ⁶ -XI
G ¹ -III R-III R ⁶ -VG ¹ -VII R-II R ⁶ -III
G ¹ -III R-III R ⁶ -VI G ¹ -VII R-II R ⁶ -VIII
G ¹ -III R-III R ⁶ -VII G ¹ -VII R-II R ⁶ -X
G ¹ -III R-III R ⁶ -VIII G ¹ -VIII R-II R ⁶ -III
G ¹ -III R-III R ⁶ -IX G ¹ -VIII R-II R ⁶ -VIII
G ¹ -III R-III R ⁶ -XG ¹ -VIII R-II R ⁶ -X
G ¹ -III R-III R ⁶ -XI G ¹ -IX RI R ⁶ -I
G ¹ -III R-IV R ⁶ -IG ¹ -IX RI R ⁶ -II
^{G 1 -III R-IV R 6} -II G 1 -IX RI R 6 -III
^{G 1 -III R-IV R 6} -III G 1 -IX RI R 6 -VIII
G ¹ -III R-IV R ⁶ -VIII G ¹ -IX RI R ⁶ -IX
G ¹ -III R-IV R ⁶ -IX G ¹ -IX RI R ⁶ -X
G ¹ -III R-IV R ⁶ -XG ¹ -IX RI R ⁶ -XI
^{G 1 -III R-IV R 6} -XI G 1 -IX R-II R 6 -I
^{G 1 -III RV R 6 -III G} 1 -IX R-II R 6 -II
G ¹ -III RV R ⁶ -VIII G ¹ -IX R-II R ⁶ -III
G ¹ -III RV R ⁶ -XG ¹ -IX R-II R ⁶ -VIII
^{G 1 -III R-VI R 6} -III G 1 -IX R-II R 6 -IX
G ¹ -III R-VI R ⁶ -VIII G ¹ -IX R-II R ⁶ -X
G ¹ -III R-VI R ⁶ -XG ¹ -IX R-II R ⁶ -XI
G ¹ -III R-VII R ⁶ -IG ¹ -IX R-III R ⁶ -I
^{G 1 -III R-VII R 6} -II G 1 -IX R-III R 6 -II
^{G 1 -III R-VII R 6} -III G 1 -IX R-III R 6 -III
^{G 1 -III R-VII R 6} -IV G 1 -IX R-III R 6 -VIII
G ¹ -III R-VII R ⁶ -VG ¹ -IX R-III R ⁶ -IX
G ¹ -III R-VII R ⁶ -VI G ¹ -IX R-III R ⁶ -X
G ¹ -III R-VII R ⁶ -VII G ¹ -IX R-III R ⁶ -XI
G ¹ -III R-VII R ⁶ -VIII G ¹ -X RI R ⁶ -I
G ¹ -III R-VII R ⁶ -IX G ¹ -X RI R ⁶ -II
G ¹ -III R-VII R ⁶ -XG ¹ -X RI R ⁶ -III
G ¹ -III R-VII R ⁶ -XI G ¹ -X RI R ⁶ -VIII
^{G 1 -III R-VIII R 6} -III G 1 -X RI R 6 -IX
G ¹ -III R-VIII R ⁶ -VIII G ¹ -X RI R ⁶ -X
G ¹ -III R-VIII R ⁶ -XG ¹ -X RI R ⁶ -XI
G ¹ -III R-IX R ⁶ -III G ¹ -X R-II R ⁶ -I
G ¹ -III R-IX R ⁶ -VIII G ¹ -X R-II R ⁶ -II
G ¹ -III R-IX R ⁶ -XG ¹ -X R-II R ⁶ -III
^{G 1 -III RX R 6 -III G} 1 -X R-II R 6 -VIII
^{G 1 -III RX R 6 -VIII G} 1 -X R-II R 6 -IX
G ¹ -III RX R ⁶ -XG ¹ -X R-II R ⁶ -X
G ¹ -III R-XI R ⁶ -III G ¹ -X R-II R ⁶ -XI
G ¹ -III R-XI R ⁶ -VIII G ¹ -X R-III R ⁶ -I
G ¹ -III R-XI R ⁶ -XG ¹ -X R-III R ⁶ -II
G ^1- III R-XII R ^6- III G ^1- X R-III R ^6- III
G ¹ -III R-XII R ⁶ -VIII G ¹ -X R-III R ⁶ -VIII
G ¹ -III R-XII R ⁶ -XG ¹ -X R-III R ⁶ -IX
G ¹ -III R-XIII R ⁶ -III G ¹ -X R-III R ⁶ -X
G ¹ -III R-XIII R ⁶ -VIII G ¹ -X R-III R ⁶ -XI
G ¹ -III R-XIII R ⁶ -XG ¹ -XI R-II R ⁶ -III
G ¹ -IV RI R ⁶ -IG ¹ -XI R-II R ⁶ -VIII
G ¹ -IV RI R ⁶ -II G ¹ -XI R-II R ⁶ -X
^{G 1 -IV RI R 6 -III G} 1 -XII R-II R 6 -III
G ¹ -IV RI R ⁶ -IV G ¹ -XII R-II R ⁶ -VIII
G ¹ -IV RI R ⁶ -VG ¹ -XII R-II R ⁶ -X
―――――――――――――――― ――――――――――――――――
Among the compounds represented by the formula (I) included in the present invention, those which can be converted into an acid addition salt according to a conventional method include, for example, hydrofluoric acid, hydrochloric acid, hydrobromic acid, hydrogen iodide Salts of hydrohalic acids such as acids, salts of inorganic acids such as nitric acid, sulfuric acid, phosphoric acid, chloric acid, perchloric acid, methanesulfonic acid, ethanesulfonic acid, trifluoromethanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid Salts of sulfonic acids such as acids, formic acid, acetic acid, propionic acid, trifluoroacetic acid, fumaric acid, tartaric acid, oxalic acid, maleic acid, malic acid, succinic acid, benzoic acid, mandelic acid, ascorbic acid, lactic acid, gluconic acid, citric acid It can be a salt of a carboxylic acid such as an acid or a salt of an amino acid such as glutamic acid or aspartic acid.

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

  As used herein, the term "pesticide" refers to a bactericide and a parasite control agent for controlling harmful pathogenic bacteria and parasites that infect and infest plants or animals. Fungicides and nematicides in the field of horticulture, or antifungals and endoparasites for animals.

  As used herein, the term "pathogenic bacteria" refers to microorganisms that cause plant diseases and animal infectious diseases, and specifically includes, for example, the following microorganisms, but specific examples of the microorganisms are not limited thereto. 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 spp. 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 spt. apiicola, S. chrysanthemella, S. helianthi, S. obesa, etc.), Sphaerulina spp., Aureobasidium spp., Kabatiella spp., Plowrightia spp., Stigmina spp., Elsinoe spp. (for example, Elsinoe ampelina, E. araliae, E. fawcettii), Sphaceloma spp. (eg, Sphaceloma caricae), Ascochyta spp. (eg, Ascochyta pisi), Corynespora spp. (eg, Corynespora cassiicola, etc.), Leptosphaeria spp. ., Phaeosphaeria spp., Ophiosphaerella spp., Setophoma spp., Helminthosporium spp., Alternaria spp. (For example, 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 turcica) , 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.) 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) , Stagonospora spp. (Eg Stagonospora sacchari, etc.), B otryosphaeria spp. (for example, Botryosphaeria berengeriana f. sp. piricola, B. dothidea, etc.), Dothiorella spp., Fusicoccum spp., Guignardia spp., Lasiodiplodia spp. spp., Phyllosticta spp. (eg, Phyllosticta zingiberis etc.), Schizothyrium spp. (eg, Schizothyrium pomi etc.), Acrospermum spp., Leptosphaerulina spp., Aspergillus spp., Penicillium spp. 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 etc.), Phyllactinia spp. (Eg, Phyllactinia kakicola, P. mali, P. malicola, etc.), Podosphaera spp. (Eg, Podosphaera fusca, P. leucotricha, P. pannosa, P. tridactyla var. tridactyla, P. xanthii, etc.), Sphaerotheca spp. (eg, Sphaerotheca aphanis var. aphanis, S. fuliginea, etc.), Uncinula spp. (eg, Uncinula necator, Un. var. necator, etc.), Uncinuliella spp. For example, Uncinuliella simulans var. Simulans, U.s. var. Tandae, Blumeriella spp. (Eg, Blumeriella jaapii), 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. (for example, Monilinia fructicola, M. fructigena, M. laxa, M. mali, M. vaccinii-corymbosi) 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 ilicicola, etc.), Candelo spp., Cylindrocarpon spp., Cylindrocladium spp., Fusarium spp. (for example, 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., Rosellinia sp. (Eg, Rosellinia necatrix, etc.), Monographella spp. (Eg, Monographella nivalis, etc.), Ophiostoma spp., Cryphonectria spp. (Eg, Cryphonectria parasitica, etc.), Diaporthe spp. (Eg, Diaporthe citri, D. kyushuensis, D. nomurai, D. tanakae) Etc.), Diaporthopsis spp., Phhomopsis 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. (for example, Valsa ceratosperma etc.), Tubakia spp., Monosporascus spp., Clasterosporium spp., Gaeumannomyces spp. Gaeumannomyces graminis, etc.), Magn aporthe spp. (such as Magnaporthe grisea), Pyricularia spp. (such as Pyricularia zingiberis), Monilochaetes infuscans, Colletotrichum spp. (such as Colletotrichum acutatum, C. capsici, C. cereale, C. destructivum, C. fragariae, mu. , C. nigrum, C. orbiculare, C. spinaciae, etc.), Glomerella spp. (Eg, Glomerella cingulata), Khuskia oryzae, Phyllachora spp. (Eg, Phyllachora pomigena, etc.), Ellisembia spp., Briosia spp., Cephalosporium spp. Eg, Cephalosporium gramineum), Epicoccum spp., Gloeocercospora sorghi, Mycocentrospora spp., Peltaster spp. (Eg, Peltaster fructicola), Phaeocytostroma spp., Philalophora spp. (Eg, Rhynchosporium secalis), Sarocladium spp., Coleophoma spp., Helicoceras oryzae and other Ascomycota phylums.

  Septobasidium spp. (Eg, Septobasidium bogoriense, S. tanakae, etc.), Helicobasidium spp. (Eg, Helicobasidium longisporum, etc.), Coleosporium spp. (Eg, Coleosporium plectranthi, etc.), Cronartium spp., Phakopsora spp. P. pachyrhizi, etc.), Physopella spp. (Eg, Physopella ampelopsidis), Kuehneola spp. (Eg, Kuehneola japonica), Phragmidium spp. (Eg, Phragmidium fusiforme, P. mucronatum, P. rosae-multiflorae, etc.), Gymnosporangium. 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, etc.), Uromyces spp. (for example, Uromyces phaseoli var. azukicola, U. 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 spp. (Eg, Exobasidium retic) , 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) (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, etc.), Typhula spp. (eg, Typhula incarnata, T. ishikariensis var. ishikariensis, etc.), Athelia spp. (eg, Athelia rolfsii, etc.), Ceratobasidium spp. (eg, Ceratobasidium cornigeiza, etc.), Cerator Rhizoctonia spp. (Eg Rhizoctonia solani etc.), Thanatephorus spp. (Eg Thanatephorus cucumeris etc.), Laetisaria spp., Waitea spp., Fomitiporia spp., Ganoderma spp., Chondrostereum purpureum, Phanerochaete spco. ) Fungi.

  Chitridiomycota fungi such as Olpidium spp.

  Blastocladiomycota fungi such as Physoderma spp.

  Fungi (Mucoromycotina) such as Choanephora spp., Choanephoroidea cucurbitae, Mucor spp. (Eg, Mucor fragilis), Rhizopus spp. (Eg, Rhizopus arrhizus, R. chinensis, R. oryzae, R. stolonifer var. Stolonifer), and the like .

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

  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. (For example, Plasmopara halstedii, P. nivea) , P. viticola, etc.), Pseudoperonospora spp. (Eg, Pseudoperonospora cubensis, etc.), Sclerophthora spp., Phytophthora spp. (Eg, Phytophthora cactorum, P. capsici, P. citricola, P. citrophthora, P. cryptaria, P. fragaria infestans, P. melonis, P. nicotianae, P. palmivora, P. porri, P. sojae, P. syringae, P. vignae f. sp. adzukicola, etc.), Pythium spp. (for example, 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. (Homerocetes).

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

  Filmictes gram-positive fungi such as Clostridium sp.

  Tenericutes Gram-positive fungi such as Phytoplasma.

  Rhizobium spp. (Eg, Rhizobium radiobacter, etc.), Acetobacter spp., Burkholderia spp. (Eg, Burkholderia andropogonis, B. cepacia, B. gladioli, B. glumae, B. plantarii, etc.), Acidovorax spp. (Eg, Acidovorax avenae subsp. Avenae) Subsp. Citrulli, A. konjaci, etc.), Herbaspirillum spp., Ralstonia spp. (For example, Ralstonia solanacearum, etc.), Xanthomonas spp. (For example, Xanthomonas albilineans, X. arboricola pv. Pruni, X. axonopodis pv. , 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. (for example, 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. s. pv. spinaciae, P. s. pv. syringae, P. s. pv. theae, P. viridiflava, Rhizobacter spp., Brenneria spp. (such as Brenneria nigrifluens), Dickeya spp. (such as Dickeya dianthicola, Proteobacteria gram such as D. zeae), Erwinia spp. (Eg, Erwinia amylovora, E. rhapontici), Pantoea spp., Pectobacterium spp. (Eg, Pectobacterium atrosepticum, P. carotovorum, P. wasabiae). Negative fungi.

  Specific examples of plant diseases and animal infectious diseases caused by infection and propagation of these pathogens include, for example, the following plant diseases and animal infectious diseases, but specific examples of plant diseases and animal infectious diseases are limited to these. It is not what is done

Plant diseases:
Peach leaf blight Leaf curl (Taphrina deformans), Plum pomegranate blight Plum pockets (Taphrina pruni), Asparagus brown spot Leaf spot (Cercospora asparagi), Sugar beet brown spot Cercospora leaf spot (Cercospora beticola), Bell pepper spot disease Frogeye leaf spot (Cercospora capsici), oyster horn spot leaf disease Angular leaf spot (Cercospora kaki), soybean purple spot disease Purple stain (Cercospora kikuchii), peanut brown spot leaf 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 circle star rot, Circular leaf spot (Mycosphaerella nawae), pea brown spot Mycosphaerella blight (Mycosphaerella pinodes), Leaf spot Mycosphaerella zingiberis), leaf mold of tomato leaf mold (Mycovellosiella fulva), leaf mold of eggplant mildew (Mycovellosiella natt) rassii), tomato rust Cercospora leaf mold (Pseudocercospora fuligena), grape brown spot Isariopsis leaf spot (Pseudocercospora vitis), Chinese cabbage leaf spot Leaf spot (Pseudocercosporella capsellae), chrysanthemum leaf spot Leaf spot (Septoria chrysantella) Leaf blight (Septoria obesa), black rot Anthracnose (Elsinoe ampelina), sardine 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 branch blight Stem canker (Leptosphaeria coniothyrium), rose black spot Leaf spot (Alternaria alternata), carrot black leaf spot Leaf blight (Alternaria dauci), pear black spot Disease Black spot (Alternaria kikuchiana), Apple spot leaf blight Alternaria blotch (Alternaria mali), Leek black spot Alternaria leaf spot (Alternaria porri), Sorghum Target spot (Bipolaris sorghicola), southern leaf blight (Cochliobolus heterostrophus), corn leaf spot Brown spot (Cochliobolus miyabeanus), garlic leaf spot Tip blight (Pleospora herbarum), barley leaf spot Stripe (Pyrenophora graminea), barley net spot blotch (Pyrenophora teres), sorghum soot spot Leaf blight (Setosphaeria turcica), corn soup spot Northern leaf blight (Setosphaeria turcica), asparagus spot spot Leaf spot (Stemphylium bottle) Scab (Venturia carpophila), apple scab (Venturia Inaequalis), pear scab (Venturia nashicola), Rosaceae Sakura subfamily, Gummy stem blight (Didymella bryoniae), burdock spot Exigua, Leaf spot (Phoma exigua var. Exigua), Streak (Phoma wasabiae), and Rot rot (Botryosphaeria berengeriana f. Sp.) piricola), Kiwi fruit soft rot (Botryosphaeria dothidea, Lasiodiplodia theobromae, Diaporthe sp.), Citrus green mold Common green mold (Penicillium digitatum), Citrus blue mold Blue mold (Penicillium italicum), Barley powdery mildew Pod wd mildew (Blumeria graminis f. sp.hordei), wheat powdery mildew Powdery mildew (Blumeria graminis f. sp. Powdery mildew (Erysiphe cichoracearum, Leveillula taurica, Sphaerotheca fuliginea), powdery mildew of carrots and parsley Powdery mildew (Erysiphe heraclei), pea powdery mildew Powdery mildew (Erysiphe pisi), tomato powdery mildew, Powderyula taurica Oidium neolycopersici, Oidium sp.), Powdery mildew (Leveillula taurica), Pumpkin powdery mildew Powdery mildew (Oidium sp., Podosphaera xanthii), bitter melon powdery mildew (Oidium sp.), oyster powdery mildew Powdery mildew (Phyllactinia kakicola), burdock powdery mildew Powdery mildew (Podosphaera fusca), apple powdery mildew Podery mildew (Podosphaera leucotricha), rose powdery mildew (Podosphaera pannosa, Uncinuliella simulans var. Simulans, U. s. Var. (Sphaerotheca aphanis var. Aphanis), watermelon and melon powdery mildew (Sphaerotheca fuliginea), grape powdery mildew (Uncinula necator, Un. Var. Necator), apple brown spot Blotch (Diplocarpon mali) , Rose spot Black spot (Diplocarpon rosae), Onion gray rot Gray mold neck rot (Botrytis allii), Gray mold Gray mold, Botrytis blight (Botrytis cinerea), Leaf blight (Botrytis cinerea, B. byssoidea, B. squamosa), Chocolate spot (Botrytis cinerea, B. elliptica, B. fabae) of broad bean, Brown rot (Monilinia fructicola) of Rosaceae , M. fructigena, M. laxa), apple monilia disease Blossom blight (Monilinia mali), Shibadara spot disease Dollar spot (Sclerotinia homoeocarpa), sclerotium disease Cottony rot, Sclerotinia rot, Stem rot (Sclerotinia sclerotiorum), rice scab False smut (Villosiclava virens), soybean black root rot (Calonectria ilicicola), wheat red mold Fusarium blight (Fusarium crookwellense, F. culmorum, Gibberella avenacea, G. zeae, Monographella nivalis), barley red mold blight Fusarium culmorum, Gibberella avenacea, G. zeae), konjac dry rot Dry rot (Fusarium oxysporum, F. solani f. Sp. Radicicola), Yam yam brown rot Brown rot (Fusarium oxysporum, F. solani f. Sp. Pisi) F. sf sp. radicicola), Adzuki wilt Fusarium wilt (Fusarium oxysporum f. sp. adzukicola), Rakkyo dry rot Fusarium basal rot (Fusarium oxysporum f. sp. allii, F. solani f. sp. radicicola), Sweet potato rot rot (Fusarium oxysporum f. Sp. Batatas, F. solani), taro dry rot (Fusarium oxysporum f. Sp. Colocasiae), cabbage, Komatsuna yellow blight Yellows (Fusarium oxysporum f. Sp. Conglutinans), banana panama disease Panama disease (Fusarium oxysporum f. Sp. Cubense), strawberry yellowing Fusarium wilt (Fusarium oxysporum f. Sp. Fragariae), lettuce root rot Root rot (Fusarium oxysporum f. Sp. Lactucae), watermelon vine Fusarium wilt Fugenium oxysporum f. Sp. Lagenariae, F. of sp. Niveum, Tomato wilt Fusarium wilt (Fusarium oxysporum f. Sp. Lycopersici), Melon vine Fusarium wilt (Fusarium oxysporum f. Sp. Melonis), Radish yellow dwarf Yellows (Fusarium oxysporum f. Sp. Raphani), Spinach wilt Fusarium wilt (Fusarium oxysporum f. Sp. Spinaciae), rice baka seedling disease “Bakanae” disease (Gibberella fujikuroi), radish black spot verticillium black spot (Verticillium albo-atrum, V. dahliae), tomato, Verticillium wilt (Verticillium dahliae), fig strain blight Ceratocystis canker (Ceratocystis ficicola), sweet potato black spot Black rot (Ceratocystis fimbriata), Cha ring leaf spot Gray blight (Pestalotiopsis longise) , 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 Brown spot (Phomopsis vexans), tea anthracnose Anthracnose (Discula theae-sinensis), apple rot Valsa canker (Valsa ceratosperma), rice blast Blast (Magnaporthe g) risea), strawberry anthrax Crown rot (Colletotrichum acutatum, C. fragariae, Glomerella cingulata), apple anthrax Bitter rot (Colletotrichum acutatum, Glomerella cingulata), cherry anthracnose Anthracnose (Colletotrichum acutatum, Glomerella anthracnose) Colletotrichum acutatum, late rot of grape Ripe rot (Colletotrichum acutatum, Glomerella cingulata), Anthracnose anthracnose (Colletotrichum acutatum), Haricot bean anthracnose Anthracnose (Colletotrichum lindemuthianum) Anthracnose (Glomerella cingulata), Chestnut anthracnose Anthracnose (Glomerella cingulata), Oyster anthracnose Anthracnose (Glomerella cingulata), Adzuki leaf blight Brown stem rot (Phialophora gregata), Leaf spot (Pseudophloeosporella dioscoreae) (Rhynchosporium secalis),
Fig rust Rust (Phakopsora nishidana), soybean rust Rust (Phakopsora pachyrhizi), rose rust Rust (Kuehneola japonica, Phragmidium fusiforme, P. mucronatum, P. rosae-multiflorae), pear scab Rust (Gymnoaticum) Tanaceti var. Tanaceti Rust (Gymnosporangium yamadae), Allium rust Rust (Puccinia allii), Chrysanthemum rust Rust (Puccinia horiana), Wheat rust Brown Rust (Puccinia recondita), Chrysanthemum rust 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 Loose smut (Ustilago nuda) Net blister blight (Exobasidium reticulatum), Blister blight (Exobasidium vexans), white rot Stem rot, Southern blight (Athelia rolfsii), chrysanthemum root rot and stem rot (Cera) tobasidium cornigerum, Rhizoctonia solani, ginger sheath blight (Rhizoctonia solani), cabbage seedling blight Damping-off (Rhizoctonia solani), honey bee blight Damping-off (Rhizoctonia solani), lettuce root blight Bottom rot (Rhizoctonia) ), Shiva leaf rot Brown patch, Large patch (Rhizoctonia solani), Rice sheath blight Sheath blight (Thanatephorus cucumeris), Sugar beet root rot Root rot / Leaf blight (Thanatephorus cucumeris),
Fig black mold Rhizopus rot (Rhizopus stolonifer var. Stolonifer),
Cruciferous clubroot Clubroot (Plasmodiophora brassicae),
Sugar beet black root disease Aphanomyces root rot (Aphanomyces cochlioides), Brassicaceae white rust (Albugo macrospora), lettuce downy mildew Downy mildew (Bremia lactucae), sengiku downy mildew Downy mildew (Peronospora chrysanthemi-coronarii), onion, Downy mildew (Peronospora destructor), downy mildew (Peronospora farinosa f. Sp. Spinaciae), spiny downy mildew, Downy mildew (Peronospora manshurica), soybean downy mildew, Downy mildew (Peronospora parasitica) ), Downy mildew (Peronospora sparsa), Downy mildew (Plasmopara halstedii), Downy mildew (Plasmopara nivea), Downy mildew (Plasmopara nivea), Downy mildew (Plasmopara viticola), Grape downy mildew Downy mildew (Pseudoperonospora cubensis), Phytophthora root rot (Phytophthora cactorum), Watermelon brown rot Brown rot (Phytophthora capsici), Phytophthora rot (Phytophthora capsici), Phytophthora blight (Phytophthora capsici), Phytophthora rot (Phytophthora cryptogea), Tomato and potato blight Late blight (Phytophthora infestans) Leaf blight (Phytophthora porri), Soybean stem disease Phytophthora root and stem rot (Phytophthora sojae), Adzuki bean stem disease Phytophthora stem rot (Phytophthora vignae f. Sp. Adzukicola) , P. myriotylum, P. paroecandrum, P. ultimum var. Ultimum), Konjac root rot (Pythium aristosporum), Corn root rot (Pythium arrhenomanes, P. graminicola), Cabbage damping damping -off (Pythium buismaniae, P. myriotylum), Root rot (Pythium myriotylum), Ginger rhizome rot Roo rot (Pythium myriotylum, P. ultimum var. ultimum), carrot spot rot Brown blotted root rot (Pythium sulcatum),
Bacterial canker (Clavibacter michiganensis subsp. Michiganensis), potato scab (Streptomyces spp.),
Crown gall (Rhizobium radiobacter), Bacterial stripe (Burkholderia andropogonis), Onion rot Soft rot (Burkholderia cepacia, Pseudomonas marginalis pv. Marginalis, Erwinia rhapontici) Bacterial grain rot (Burkholderia gladioli, B. glumae), Bacterial fruit blotch (Acidovorax avenae subsp. Citrulli), konjac leaf blight Bacterial leaf blight (Acidovorax konjaci), Bacterial wilt (Ralstonia solana) Bacterial shot hole (Xanthomonas arboricola pv. Pruni, Pseudomonas syringae pv. Syringae, Brenneria nigrifluens), Peach black spot Bacterial leaf spot (Xanthomonas arboricola pv. vitians), Brassicaceae black rot (Xanthomonas campestris pv. campestris), soybean leaf blight Bacterial pustule (Xanthomonas ca Bacterial spot (Xanthomonas campestris pv. nigromaculans), Bacterial spot (Xanthomonas campestris pv. vesicatoria), Citrus canker (Cantrus canker), Xanthomonas citri subsp. cisp. Rot (Pseudomonas cichorii, P. marginalis pv. Marginalis, Erwinia sp.), Lettuce rot Bacterial rot (Pseudomonas cichorii, P. marginalis pv. Marginalis, P. viridiflava), Kiwi fruit flower rot bacterial bacterium Bacterial blossom blight (Pseudomonas) marginalis, P. syringae pv. syringae, P. viridiflava), Kiwifruit canker Bacterial canker (Pseudomonas syringae pv. actinidiae), Loquat canker disease Canker (Pseudomonas syringae pv. eriobotryae) Disease Bacterial spot (Pseudomonas syringae pv. Lachrymans), Brassicaceae black spot bacterial disease Bacterial black spot (Pseudomonas syringae pv. Maculicola), Plum blight disease B acterial canker (Pseudomonas syringae pv. morsprunorum, Erwinia sp.), tea red blight Bacterial shoot blight (Pseudomonas syringae pv. theae), leek soft rot Bacterial soft rot (Dickeya sp., Pectobacterium carotovorum), Rosaceae Burn blight Fire blight (Erwinia amylovora), konjac rot Soft rot (Pectobacterium carotovorum), soft rot Bacterial soft rot (Pectobacterium carotovorum).

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

  As used herein, the term "parasite" refers to a plant-parasitic nematode parasitic on a plant, an animal-parasitic nematode parasitic on an animal, a hookhead, a flatworm, a protozoan, and the like. For example, the following parasites may be mentioned, but specific examples of the parasite are not limited thereto.

  Giant kidney worm (Dioctophyma renale), Thread worms (Capillaria annulata), Circular torsion Cropworm (Capillaria contorta), Capillary liver worm (Capillaria hepatica), Capillary liver worm (Capillaria hepatica) perforans), Philippine capillary nematode (Capillaria philippinensis), pig capillary nematode (Capillaria suis), whipworm Whipworm (Trichuris discolor), sheep 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).

  Sticks such as Intestinal threadworm (Strongyloides papillosus), cat feces nematode (Strongyloides planiceps), pig feces nematode Pig threadworm (Strongyloides ransomi), human feces nematode Threadworm (Strongyloides stercoralis), and Micronema spp. Nematode (Rhabditida) nematodes.

  Hookworm (Ancylostoma braziliense), Dog hookworm (Ancylostoma caninum), Zubini hookworm Old World hookworm (Ancylostoma duodenale), Cat hookworm (Ancylostoma tubaeforme), Narrow head hookworm The Northern hookworm of dogs (Uncinaria stenoce) The hookworm Cattle hookworm (Bunostomum phlebotomum), the sheep hookworm Small ruminant hookworm (Bunostomum trigonocephalum), the American hookworm New World hookworm (Necator americanus), the genus Cyatostomum (Cyathostomum spp.), The genus Cylicocyclus spp. spp.), Cylicostephanus spp., Donkey beetle (Strongylus asini), edentulous beetle (Strongylus edentatus), horse beetle Blood worm (Strongylus equinus), common worm Blood worm (Strongylus vulgaris) , Large-mouthed bowel worm (Chabertia ovina), an Indian intestinal nodule Nodular worm (Oesophagostomum brevic) audatum), Nodule worm (Oesophagostomum columbianum), Nodule worm (Oesophagostomum dentatum), Nodule worm (Oesophagostomum dentatum), Nodular worm (Oesophagostomum georgianum), Nodular worm (Oesophagostomum maplei) Nodular worm (Oesophagostomum quadrispinulatum), cattle intestinal nodule Nodular worm (Oesophagostomum radiatum), goat intestinal nodule Nodular worm (Oesophagostomum venulosum); Swine kidney worm (Stephanurus dentatus), Cooperia cattle bankrupt worm (Cooperia oncophora), red stomach worm (Hyostrongylus rubidus), stomach hair worm (Trichostrongylus axei), serpentine worm (Trichostrongylus colubriformis), the oriental hairy nematode Oriental trichostrongylus (Trichostrongylus orientalis), and the red stomach worm (Haemonchus co) ntortus), Cattle stomach worm (Mecistocirrus digitatus), Ostertag worm (Ostertagia ostertagi), Common lungworm (Dictyocaulus filaria), Bovine lungworm (Dictyocaulus viviparus) Insects Thin-necked intestinal worm (Nematodirus filicollis), swine lung worm Swine lungworm (Metastrongylus elongatus), dog lung worm Lungworm (Filaroides hirthi), lung capillary nematode Lungworm (Crenosoma aerophila), fox lung worm Fox lungworm (Crenosoma vulpis) Strongylida (Strongylida) nematodes such as the Cantonese nematode Rat lung worm (Angiostrongylus cantonensis), the squid nematode French heartworm (Angiostrongylus vasorum), and the genus Protostrongylus spp.

  Rice white-tip nematode Rice white tip nematode (Aphelenchoides besseyi), strawberry nematode Strawberry foliar nematode (Aphelenchoides fragariae), Hagare nematode Chrysanthemum foliar nematode (Aphelenchoides ritzemabosi) Aphelenchida) nematodes.

  Potato cyst nematode White potato cyst nematode (Globodera pallida), potato cyst nematode Potato cyst nematode (Globodera rostochiensis), wheat cyst nematode Cereal cyst nematode (Heterodera avenae), soybean cyst nematode (Soybean cyst nematode) cyst nematode (Heterodera schachtii), clover cyst nematode (Clover cyst nematode (Heterodera trifolii), arenalian root-knot nematode (Meloidogyne arenaria), northern root-knot nematode (Meloidogne-knot nematode) (Meloidogyne incognita), Java root-knot nematode (Meloidogyne javanica), Apple root-knot nematode (Meloidogyne mali), Southern root nematode Cof fee root-lesion nematode (Pratylenchus coffeae), saw-toothed nematode (Pratylenchus drenatus), chanegesaresenchu Tea root-lesion nematode (Pratylenchus loosi), Muginekosaresenchu California root-lesion nematode (Pratylenchus negude) -lesion nematode (Pratylenchus penetrans); Walnut root-lesion nematode (Pratylenchus vulnus); (Tylenchida) nematodes.

Pinworm (Oxyurida) nematodes such as human pinworm Pinworm (Enterobius vermicularis), equine pinworm Equine pinworm (Oxyuris equi), rabbit pinworm Rabbit pinworm (Passalurus ambiguus)
Pig roundworm (Ascaris suum), horse roundworm Horse roundworm (Parascaris equorum), small roundworm Dog roundworm (Toxascaris leonina), dog roundworm Dog intestinal roundworm (Toxocara canis), cat roundworm Feline roundworm (Toxocara cati), cattle roundworm Large Ascaridida such as cattle roundworm (Toxocara vitulorum), Anisakis spp., Pseudoterranova spp., Caecal worm (Heterakis gallinarum), Chicken roundworm (Ascaridia galli), etc. Nematode.

  Guinea worm (Dracunculus medinensis), Dolores jaw-and-mouth worm (Gnathostoma doloresi), Hard spine-to-mouth worm (Gnathostoma hispidum), Japanese jaw-and-mouth worm (Gnathostoma nipponicum), Reddish-coloured worm (Gnathostoma spinigerum) , Dog stomach worm (Physaloptera canis), Cat stomach worm Cat stomach worm (Physaloptera felidis, P. praeputialis), Lara stomach worm Feline / canine stomach worm (Physaloptera rara), Oriental eye worm Eye worm (Thelazia callipaeda), Bovine eyeworm (Thelazia rhodesi), Large mouth stomach worm (Draschia megastoma), Echine stomach worm (Habronema microstoma), Stomach worm (Habronema muscae), Gullet worm Gongylonema pulchrum), Thick stomach worm (Ascarops strongylina), bovine parafilaria (Parafilaria bovicola), bovine parafilaria (Parafilaria multipapillosa), Okinawa filamentous worm (Stephanofilaria) okinawaensis), Bancroft filaria (Wuchereria bancrofti), Malay (Brugia malayi), Neck threadworm (Onchocerca cervicalis), Gibson (Onchocerca gibsoni), Cattle filarial ut (Onchocer) ), Helminth (Onchocerca volvulus), finger worm Bovine filarial worm (Setaria digitata), sternworm Peritoneal worm (Setaria equina), lip papillary worm (Setaria labiatopapillosa), marshallian worm (Setaria marshalli), dog Spirurida nematodes such as the filamentous worm Dog heartworm (Dirofilaria immitis) and the lower filamentous worm African eye worm (Loa loa).

  Hookworms such as chain hookheads (Moniliformis moniliformis) and giant thorny-headed worms (Macracanthorhynchus hirudinaceus).

  Pseudolobes such as Fish tapeworm (Diphyllobothrium latum), Diphyllobothrium nihonkaiense, Manson tapeworm (Spirometra erinaceieuropaei), and large diploid worm (Diplogonoporus grandis) Eye (Pseudophyllidea) tapeworm.

  Wire tapeworm (Mesocestoides lineatus), circumscribed tapeworm Chicken tapeworm (Raillietina cesticillus), spiny groove tapeworm Fowl tapeworm (Raillietina echinobothrida), square tapeworm Chicken tapeworm (Raillietina tetragona), cystic tapeworm Canine tapeworm (Taenia hydatigena), Canine tapeworm (Taenia multiceps), Sheep measles (Taenia ovis), Dog tapeworm (Taenia pisiformis), Beef tapeworm (Taenia saginata), and Tapeworm (Taenia serialis) ), Tapered tapeworm Pork tapeworm (Taenia solium), Cat tapeworm Feline tapeworm (Taenia taeniaeformis), Hydatid tapeworm (Echinococcus granulosus), Multi worm tape Small fox tapeworm (Echinococcus multilocularis), Wild cat tapeworm (Echinococcus oligarthrus), Fogel tapestrum (Echinococcus vogeli), reduced tapeworm Rat tapeworm (Hymenolepis diminuta), small tapeworm Dwarf tapeworm (Hymenolepis nana), double-pored dog tapeworm (Dipylidium ca) ninum), cuneiform tapeworm (Amoebotaenia sphenoides), funnel tapeworm (Choanotaenia infundibulum), quail tapeworm (Metroliasthes coturnix), large tapeworm Equine tapeworm (Anoplocephala magna), foliate tapeworm Cecal tapeworm (Anoplocephala perfoliata) Cyclophyllidea tapeworms such as Dwarf equine tapeworm (Paranoplocephala mamillana), Beneden tapeworm Common tapeworm (Moniezia benedeni), extended tapeworm Sheep tapeworm (Moniezia expansa), and Stilesia spp. (Stilesia spp.).

  Stripeididae such as Pharyngostomum cordatum, Schistosoma haematobium, Schistosoma haematobium, Schistosoma haematobium, Schistosoma japonicum, Schistosoma japonicum and Schistosoma mansoni.

  Echinostoma cinetorchis, Echinostoma cinetorchis, Echinostoma hortense, Giant liver fluke (Fasciola gigantica), Common liver fluke (Fasciola hepatica), Fleur fluke (Fasciolopsis buski) Echinostomidae, such as Homalogaster paloniae.

  Continental spearworm (Dicrocoelium chinensis), spearworm Lancet liver fluke (Dicrocoelium dendriticum), African spearworm African lancet fluke (Dicrocoelium hospes), small pancreatic fluke (Eurytrema coelomaticum), pancreatic fluke Pancreatic fluke (Eurytrema pancreaticum) Paramecium flukes (Plagiorchiida), such as Paragonimus miyazakii, Paragonimus ohirai, and Lung fluke (Paragonimus westermani).

  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), Pseudoamphistomum sp. .), Methochis spp., Parametorchis spp., Intestinal fluke (Heterophyes heterophyes), Metagonimus yokokawai, Pygidiopsis summa, etc. Opisthorchiida) fluke.

  Amoeba such as dysentery amoeba (Entamoeba histolytica, E. invadens).

  Futago Babesia (Babesia bigemina), Cattle Babesia (Babesia bovis), Large Horse Babesia (Babesia caballi), Dog Babesia (Babesia canis), Cat Babesia (Babesia felis), Gibson Dog Babesia (Babesia gibsoni), Large Piroplasma (Babesia ovata) ), Cytauxzoon felis, tropical piroplasmosis theileria (Theileria annulata), pseudocoastal heat theileria (Theileria mutans), small piroplasma (Theileria orientalis), east coast heat theileria (Theileria parva), etc. Piroplasmida sporozoa.

  Haemoproteus mansoni, chicken leukocytozoon caulleryi, Plasmodium falciparum, Plasmodium malariae, Oval malaria parasite, Plasmodium ovale Haemosporida sporozoites such as protozoa (Plasmodium vivax).

  Caryospora spp., Eimeria acervulina, Eimeria bovis, Eimeria brunetti, Eimeria brunetti, Eimeria maxima, Eimeria necatrix, Eimeria necatrix Obinoidaris (Eimeria ovinoidalis), rabbit liver coccidium (Eimeria stiedae), chicken caecum coccidium (Eimeria tenella), dog isospora (Isospora canis), cat isospora (Isospora felis), pig isospora (Isospora suis), Tizzeria alli , Tyzzeria anseris, Tyzzeria perniciosa, Wenyonella anatis, Wenyonella gagari, Cryptosporidium dog, Cryptosporidium cat Spordium (Cryptosporidium felis), Human Cryptosporidium (Cryptosporidium hominis), Turkey Cryptosporidium (Cryptosporidium meleagridis), Murine Cryptosporidium (Cryptosporidium muris), Small Cryptosporidium (Cryptosporidium sarcoplasma) (Sarcocystis cruzi), Sarcocystis felis, Sarcocystis hominis, Sarcocystis miescheriana, Sarcocystis neurona, Sarcocystis nericella, Sarcocystis nerus s. Eucoccidae (Eucoc) such as Sarcocystis ovalis, Toxoplasma gondii, dog hepatozon (Hepatozoon canis), and cat hepatozon (Hepatozoon felis) cidiorida) sporozoa.

  Vestibuliferida ciliates such as colonic Balantidium coli.

  Trichomonadidae flagellates such as Histomonas meleagridis, intestinal Tricomonas (Pentatrichomonas hominis), and oral Trichomonas tenax.

  Diplomonadida flagellates such as Giardia intestinalis, Giardia muris, Hexamita meleagridis, and Hexamita parva.

  Leishmania donovani, Leishmania infantum, Leishmania major, Tropical Leishmania tropica, Gambia Trypanosoma brucei gambiense, Trypanosoma brucei rhodessi Kinetoplastidae flagellates such as Trypanosoma cruzi, Trypanosoma equiperdum, and Evans trypanosoma evansi.

  In the present specification, the term "plant" refers to cereals, fruit trees and vegetables, feed crops such as livestock and poultry that are cultivated as human food, appreciation plants that love their shapes and shapes, or plantings such as parks and streets. It means a vascular plant (Tracheophyta), and specific examples include the following plants, but specific examples of the plant are not limited thereto.

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

Magnoliids (magnoliids) belonging to the family Pepperaceae, such as pepper Pepper (Piper nigrum), the camphoraceous family (Lauraceae), such as avocado Avocado (Persea americana),
Araceae (Aiosae) such as Konjac (Amorphophallus konjac), taro Eddoe (Colocasia esculenta) and the like (Araceae); Chinese yam (Dioscorea batatas); porrum), onion Onion (Allium cepa), Rakkyo (Allium chinense), leek Welsh onion (Allium fistulosum), garlic Garlic (Allium sativum), chives Chives (Allium schoenoprasum), Asatsuki Chive (Allium schoenopliosum) Leek Oriental garlic (Allium tuberosum), Scallion (Allium x wakegi) and other leek family (Alliaceae), asparagus Asparagus (Asparagus officinalis) and other cedar family (Asparagaceae), coconut palm Cocoonut palm (Cocos nucifera), and guinea palm (Arecaceae) such as (Elaeis guineensis) and Arecoideae (Arecoideae); Date palm (Phoenix dactylifera) such as Arecaceae, Taripot subfamily (Coryphoideae), pineapple Pineapple (Ananas comosus) and other pineapple family (Bromeliaceae), rice Rice (Oryza sativa) and other rice family (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) and the like. Poaceae (Poaceae), Poaceae (Poooae), Bermuda grass (Cynodon dactylon), Grass (Zoysia spp.), Etc. Sorgum (Sorghum bicolor), corn Corn (Zea mays), etc., Poaceae; millet subfamily (Panicoideae); banana, Banana (Musa spp.), Etc. Monocotyledons (monocots) belonging to the family Zingiberaceae such as Musaceae, Myoga Myoga (Zingiber mioga) and Ginger Ginger (Zingiber officinale).

  Lotus root (Nelumbo nucifera) and other Lotus family (Nelumbonaceae), peanut Peanut (Arachis hypogaea), chickpea Chickpea (Cicer arietinum), lentil Lentil (Lens culinaris), pea Pea (Pisum sativum), and broad bean Broad bean , Soybean (Glycine max), Soybean (Glycine max), Common Bean (Phaseolus vulgaris), Adzuki bean (Vigna angularis), Cowpea (Vigna unguiculata) and other legumes (Fabaceae), Hop Hop (Humulus lupulus) and aceae (Cannabaceae) ), Fig Fig Tree (Ficus carica), mulberry family (Moraceae) such as mulberry Mulberry (Morus spp.), Buckthorn family (Rhamnaceae) such as jujube Common jujube (Ziziphus jujuba), strawberry Strawberry (Fragaria), rose Rose (Rosa) spp.), Rose 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 subfamilies (Maloideae), peaches Peach (Amygdalus persica), apricots Apricot (Prunus armeniaca), sweet cherry Cherry (Prunus avium), prunes Rosaceae such as Prune (Prunus domestica), Almond (Prunus dulcis), Japanese apricot (Prunus mume), Japanese plum (Prunus salicina), Japanese plum (Cerasus speciosa), Yoshino cherry (Cerasus x yedoensis 'Somei-yoshino') (Rosaceae) Sakura subfamily (Prunoideae), poisonous winter melon (Benincasa hispida), watermelon Watertermelon (Citrullus lanatus), yugao Bottle gourd (Lagenaria siceraria var. , Zucchini (Cucurbita pepo), Bitter melon (Momordica charantia var. Pavel), Melon Muskmelon (Cucumis melo), Oriental pi ckling melon (Cucumis melo var. conomon), makuwauri Oriental melon (Cucumis melo var. makuwa), cucumber Cucumber (Cucumis sativus) and other Cucurbitaceae (Cucurbitaceae), chestnut Japanese Chestnut (Castanea crenata) and other beech family (Fagaceae), Walnuts (Juglandaceae) such as Walnut (Juglans spp.), Cashew nuts Cashew (Anacardium occidentale), Mango Mango (Mangifera indica), Pistachio Pistachio (Pistacia vera) etc., Anacardiaceae, Japanese pepper (Zanthoxylum) ), Such as Rutaceae, Subfamily Henruda (Rutoideae), Daidai Bitter orange (Citrus aurantium), Lime Lime (Citrus aurantifolia), Hassaku orange (Citrus hassaku), Yuzu Yuzu (Citrus junos), Lemon Lemon (Citrus limon) ), Natsumikan (Citrus natsudaidai), Grapefruit Grapefruit (Citrus x paradisi), Orange Orange (Citrus sinensis) ), Kabosu Kabosu (Citrus sphaerocarpa), Sudachi Sudachi (Citrus sudachi), Ponkan Mandarin Orange (Citrus tangerina), Unshu mandarin Satsuma (Citrus unshiu), Kumquat Kumquat (Fortunella spp.), Etc. Aurantioideae), horseradish Horseradish (Armoracia rusticana), mustard Mustard (Brassica juncea), Takana Takana (Brassica juncea var. oleracea var. capitata, Brussels sprout (Brassica oleracea var. gemmifera), Broccoli (Brassica oleracea var. italica), Chingensai Green pak choi (Brassica rapa var. 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. Longipinnatus), Brassicaceae such as Wasabi (Wasabia japonica), Papaya family (Caricaceae) such as Papaya (Carica papaya), Okra Okra (Abelmoschus esculentus), Cotton plant (Gossypium). Malvaceae such as Cacao (Theobroma cacao), grape (Vitaceae) such as grape (Vitis spp.), Sugar beet Sugar beet (Beta vulgaris ssp. Vulgaris var. Altissima), table beet Table beet (Beta) Vulgaris ssp. Vulgaris var. vulgaris), Spinach (Spinacia oleracea) and other Amaranthaceae (Amaranthaceae), Buckwheat Buckweat (Fagopyrum esculentum) and other Polygonaceae (Polygonaceae) Oyster family (Ebenaceae), such as oyster Kaki Persimmon (Diospyros kaki); camellia family (Theaceae), such as tea plant (Camellia sinensis); kiwifruit (Actinidia deliciosa, A. chinensis), such as actinidiaceae; Ericaceae, such as Blueberry (Vaccinium spp.) And Cranberry (Vaccinium spp.), Rubiaceae, such as Coffee plants (Coffea spp.), Lemon balm (Melissa officinalis), Mint Mint ( Lamiaceae such as Mentha spp., Basil Basil (Ocimum basilicum), perilla Shiso (Perilla frutescens var. Crispa), perilla (Perilla frutescens var. Frutescens), sage Common Sage (Salvia officinalis), and thyme Thyme (Thymus spp.) (Lamiaceae), Sesame (Sesamum indicum) and other sesame families (Pedaliaceae), olive Olive (Olea europaea) and other Oleaceae families (Oleaceae), sweet potato Sweet potato (I Convolvulaceae, such as pomoea batatas, Tomato Tomato (Solanum lycopersicum), Eggplant Eggplant (Solanum melongena), Potato Potato (Solanum tuberosum), Pepper Chili pepper (Capsicum annuum), Bell pepper Bell pepper (Capsicum annus var. '), Solanaceae (Solanaceae) such as tobacco (Nicotiana tabacum), celery Celery (Apium graveolens var. sativus), Parsley (Petroselium crispum), Italian parsley (Petroselinum neapolitanum), etc., Apiaceae (Apiaceae), Udo Udo (Aralia cordata), Uranaceae (Aralia elata), etc., Araliaceae oke, artichoke (Asteraceae) such as (Cynara scolymus), thistle subfamily (Carduoideae), and Chicory (Cichorium intybus), lettuce Lettuce (Lactuca sativa), etc., Asteraceae (Asteraceae), dandelion subfamily (Asteraceae), chrysanthemum Florists' daisy (Dendranthema grandiflorum), shungiku Crown daisy (Glebionis coronaria), sunflower Sunflower (Helianth anus) True dicots (eudicots) belonging to the Asteraceae family (Asteraceae) such as Fuki (Petasites japonicus) and Burdock Burdock (Arctium lappa).

  As used herein, the term "animal" refers to humans, companion animals, companion animals, livestock and poultry, and vertebrates (Vertebrata) such as research and experimental animals, and specific examples include the following animals. However, specific examples of animals are not limited to these.

  Capuchin family (Cebidae) such as Tufted capuchin (Cebus apella), cynomolgus monkey Crab-eating macaque (Macaca fascicularis), rhesus monkey Rhesus macaque (Macaca mulatta) etc. (Hominidae) such as (Homo sapiens), Rabbit (Leporidae) such as European rabbit (Oryctolagus cuniculus), Chinchillidae such as Long-tailed chinchilla (Chinchilla lanigera), Guinea pig (Cavia porcellus) (Caviidae), Golden hamster (Mesocricetus auratus), Djungarian hamster (Phodopus sungorus), Chinese hamster (Cricetulus griseus), etc. , House mouse ouse (Mus musculus), Black Rat (Rattus rattus), etc., Muridae, Chipmunk Chipmunk (Tamias sibiricus), etc. (Sciuridae), Dromedary (Camelus dromedarius), Bactrian camel (Camelus), Bactrian camel (Camelus) Camelidae such as Alpaca (Vicugna pacos) and Llama (Lama glama); Boars (Suidae) such as pig Pig (Sus scrofa domesticus); Reindeer Reindeer (Rangifer tarandus); Red deer (Cervus elaphus) Bovidae (Cervidae), Yak (Bos grunniens), Cattle Cattle (Bos taurus), Water Buffalo (Bubalus arnee), Goat Goat (Capra hircus), Sheep Sheep (Ovis aries), etc. ), Cats (Felidae cats) such as cat (Felis silvestris catus), dogs (Canidae) such as domestic dogs (Canis lupus familiaris), red fox Red fox (Vulpes vulpes), -European mink (Mustela lutreola), American mink (Mustela vison), ferret Ferret (Mustela putorius furo), etc., Mustelidae, donkey Donkey (Equus asinus), equine Horse (Equus caballus), etc. Mammals (Mammalia) belonging to the kangaroo family (Macropodidae) such as Equidae) and red kangaroo (Macropus rufus).

  Ostrich (Struthionidae) such as Ostrich (Struthio camelus), Rareidae (Rheidae) such as American rhea (Rhea americana), Emu Emu (Dromaius novaehollandiae) such as Emu (Dromaiidae), and grouse Patramigan (Lagopus muta) , Turkey Wild turkey (Meleagris gallopavo), quail Japanese quail (Coturnix japonica), chicken Chicken (Gallus gallus domesticus), common pheasant Common pheasant (Phhasianus colchicus), Golden pheasant (Chrysolophus pictus), Indian pheasant, Indian pheasant (Chrysolophus pictus) Phasianidae (Phasianidae), Guineafowl Helmeted guineafowl (Numida meleagris), etc., Guinea butterfly family (Numididae), Mallard Mallard (Anas platyrhynchos), Duck Domesticated duck (Anas platyrhynchos var. ), Greylag goose (Anser anser), Sakatsu Duck family (Anatidae) such as Lagan Swan goose (Anser cygnoides), Whooper swan (Cygnus cygnus), Mute swan Mute swan (Cygnus olor), etc .; Pigeon family (Columbidae) such as turtle dove (Streptopelia turtur), Sulfur-crested cockatoo (Cacatua galerita), yellow-winged parakeet Galah (Eolophus roseicapilla), cockatiel (Nymphicus hollandicus) such as cockatiel (Nymphicus hollandicus), and parrot family (Cafacedae) such as cockatiel (Nymphicus hollandicus) (Agapornis roseicollis), Blue-and-yellow macaw (Ara ararauna), Macaw Scarlet Macaw (Ara macao), Budgerigar (Melopsittacus undulatus), Parrot African African parrot (Psittacus erithacus), etc. Common hill myna (Gracula religiosa) etc. Species of the Eurasian family (Sturnidae), Red avadavat (Amandava amandava), Zebra finch (Taeniopygia guttata), Bengalese finch (Lonchura striata var. Domestica), Buncho Java sparrow (Padda oryzivora), etc. Birds (Aves) belonging to the family Atriaceae (Fringillidae) such as the canary Domestic canary (Serinus canaria domestica) and European goldfinch (Carduelis carduelis).

  Chameleon family (Chamaeleonidae) such as Eve deer chameleon (Chamaeleo calyptratus), green iguana Green iguana (Iguana iguana), green anole Carolina anole (Anolis carolinensis) such as Iguanidae, Nile monitor lizard Nile monitor Monitor lizard Water monitor (Varanus salvator) and other monitor lizards (Varanidae), dragon lizards Solomon islands skink (Corucia zebrata) and other lizards (Scincidae), Sudinamera Beauty rat snake (Elaphe taeniura) and other lobsters (Collaidae) Common snapping turtle (Chehe) of the Python family (Pythonidae) such as constrictor (Boa constrictor), Indian python (Python molurus), Reticulated python (Python reticulatus) such as constrictor (Boa constrictor); (Chelydridae), Kisuga Diamondback terrapin (Malaclemys terrapin), Redhead turtle Pond slider (Trachemys scripta), etc., Pond turtle family (Emydidae), Japanese pond turtle (Mauremys japonica), etc .; (Testudinidae), Soft-shelled turtle (Pelodiscus sinensis), etc., Tritonchidae, American alligator American alligator (Alligator mississippiensis), Black caiman (Melanosuchus niger), etc. reptiles (Reptilia) belonging to the Crocodylidae (Crocodylidae) such as siamensis).

  Carp (Cyprinus carpio), goldfish (Carassius auratus auratus), zebrafish Zebrafish (Danio rerio), etc., carp family (Cyprinidae), coulis roach Kuhli loach (Pangio kuhlii), etc., loach family (Cobitidae), piranha natterii piranha (Pygocentrus nattereri), neon tetra (Neon tetra (Paracheirodon innesi), etc.), Characidae, Shinanoyukimasa Maraena whitefish (Coregonus lavaretus maraena), Coho salmon (Oncorhynchus kisutsh), Rainbow trout Rainbow trout (Oncorhynchus) Oncorhynchus tshawytscha), Atlantic salmon Atlantic salmon (Salmo salar), brown trout Brown trout (Salmo trutta) and other salmonids (Salmonidae); Pseudanthias squamipinnis), Que Longtoo Groupers (Serranidae) such as th grouper (Epinephelus bruneus) and Mahata Convict grouper (Epinephelus septemfasciatus); Sunfish family (Centrarchidae) such as bluegill (Lepomis macrochirus); dumerili), yellowtail Japanese amberjack (Seriola quinqueradiata), etc., Carangidae, red sea bream (Pagrus major), etc .; ), Actinopterygii belonging to the Pacific mackerel family (Scombridae) such as Pacific bluefin tuna (Thunnus orientalis), and Japanese pufferfish (Takifugu rubripes) such as Japanese pufferfish (Tetraodontidae).

  The term "useful insects" as used herein refers to insects that are useful for human life by utilizing the product or that are useful for improving the efficiency of agricultural work such as use for pollination of fruit trees and vegetables. For example, Japanese honeybee Japanese honeybee (Apis cerana japonica), Western honeybee Western honey bee (Apis mellifera), bumblebee Bumblebee (Bombus consobrinus wittenburgi, B. diversus diversus, B. hypocrita hypocrita, B. nititris, e. (Osmia cornifrons), silkworm Silkworm (Bombyx mori) and the like, but specific examples of useful insects are not limited to these.

  As used herein, the term `` natural enemy '' refers to an organism that kills or inhibits the reproduction of a specific species of organisms by predation or parasitism, in particular, a specific species of organisms that attack crops, and specifically, for example, The following creatures can be mentioned, but specific examples of natural enemies are not limited to these.

  Braconidae; (Aphelinus asychis), cotton duck bee (Aphelinus gossypii), cros dia wasp (Aphelinus maculatus), dwarf wasp (Aphelinus varipes), horned bee wasp (Encarsia formosa), mackerel wasp (Eretmocerus eremicus), wasp (Aphelinidae) such as mundus and Chrysocharis pentheus; Parasitic wasp; Parasitic wasp belonging to the family Eulophidae; japonica); Anthocoridae (Anthocoridae) belonging to the family Antocoridae, such as Minute pirate bug (Orius strigicollis), such as Oriental stink bug (Orius minutus); Predatory mirids of the predatory stink bugs (Pilophorus typicus) and tobacco turtles (Nesidiocoris tenuis) such as the miridae; Predatory mirid; Aeolothrip Predatory thrips belonging to idae); Diptochrysa formosanus; Chrysoperla nipponensis; etc .; Green lacewing; Predatory mite belonging to the family Phytoseiidae (Phytoseiidae), such as Amblyseius degenerans, Amblyseius swirskii, Phytoseiulus persimilis, and the like, Predatory mite; (Misumenops tricuspidatus).

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

  Manufacturing method A

Formula (II) wherein Y ¹ , Y ² , R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ have the same meaning as described above. And a salt thereof (for example, hydrochloride, hydrobromide, trifluoroacetate, p-toluenesulfonate, etc.) and a compound of the formula (III) wherein G ¹ has the same meaning as described above. J ¹ represents a chlorine atom, a bromine atom, a C ₁ -C ₄ alkylcarbonyloxy (eg, pivaloyloxy), a C ₁ -C ₄ alkoxycarbonyloxy (eg, isobutyloxycarbonyloxy) or an azolyl (eg, imidazole-1-). Ile). With benzene, toluene, dichloromethane, chloroform, 1,2-dichloroethane, diethyl ether, tert-butyl methyl ether, tetrahydrofuran, 1,4-dioxane, ethyl acetate, N, N- Using dimethylformamide, N, N-dimethylacetamide, acetonitrile, water or a mixture of two or more thereof in any proportion as a solvent, if necessary, 1 to 1 equivalent of the compound represented by the formula (II) 0 ° C. to reflux temperature of the reaction mixture in the presence of 3 equivalents of a base such as sodium carbonate, potassium carbonate, sodium bicarbonate, sodium acetate, triethylamine, ethyldiisopropylamine, N-methylmorpholine, pyridine, 4- (dimethylamino) pyridine, etc. By reacting in a temperature range of from 30 minutes to 24 hours to obtain the compound of the formula (I) [wherein G ¹ , Y ¹ , Y ² , R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ have the same meaning as described above. The present invention compound represented by the formula:

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

  Manufacturing method B

Formula (Ia) wherein R ⁵ is a hydrogen atom in Formula (I) [wherein G ¹ , Y ¹ , Y ² , R ¹ , R ² , R ³ , R ⁴ and R ⁶ represent the same meaning as described above. . And 1 to 10 equivalents of the compound of the formula (IV) [wherein R ⁵ is a hydrogen atom, —OH, a C _{1 to} C ₄ alkoxy and a C _{1 to} C ₄ haloalkoxy other than the above. And J ² represents a chlorine atom, a bromine atom, an iodine atom, a C ₁ -C ₄ alkylcarbonyloxy (eg, pivaloyloxy), a C ₁ -C ₄ alkylsulfonate (eg, methanesulfonyloxy), ₁ -C ₄ haloalkylsulfonate (for example, trifluoromethanesulfonyloxy, etc.), arylsulfonates (e.g., benzenesulfonyloxy, p- toluenesulfonyloxy, etc.) or azolyl (for example, imidazol-1-yl, etc.) good leaving such Represents a group. And a polar solvent such as tert-butyl methyl ether, tetrahydrofuran, 1,4-dioxane, acetonitrile or N, N-dimethylformamide, if necessary, and the compound represented by the formula (Ia) if necessary. 10 equivalents to 24 equivalents 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. By reacting for a time, formula (I) wherein G ¹ , Y ¹ , Y ² , R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ have the same meaning as described above. The present invention compound represented by the formula:

  Some of the compounds represented by the formula (IV) used here are known compounds, and some of them are commercially available. In addition, other synthetic methods described in the literature relating to known compounds, for example, Chemical and Pharmaceutical Bulletin [Chem. Pharm. Bull.] 1986, 34, 540 and 2001, 49 Volume 1102, Journal of the American Chemical Society [J. Am. Chem. Soc.] 1964, 86, 4383, The Journal of Organic Chemistry [J. Org. Chem. . 1983, 48, 5280, Organic Synthesis [Org. Synth.] 1988, Collective Volume 6, 101, Synlett 2005, 2847, Synthesis 1990, 1159 , Japanese Patent Application Publication (JP 05/125017), European Patent Publication (EP 0,051,273), British Patent Publication (GB 2,161,80) No. 2) and the like.

  Manufacturing method C

Formula (V) [wherein G ¹ , Y ¹ , Y ² , R ¹ , R ² , R ³ , R ⁴ and R ⁵ represent the same meaning as described above, and J ³ represents a bromine atom, an iodine atom or C ₁ -C ₄ haloalkylsulfonate (for example, trifluoromethanesulfonyloxy, etc.) represents a good leaving group such as. The compound represented by the formula (VIa) [wherein R ⁶ is the same as that of the general Sonogashira coupling reaction described in, for example, International Patent Application Publication (WO 2012/028676). Has the same meaning as Or a substituted acetylene represented by, for example, Bioorganic and Medicinal Chemistry Letters [Bioorg. Med. Chem. Lett.] 2004, 14, 3993, Journal of Medicinal. According to the method described in Chemistry [J. Med. Chem.] 2006, 49, 1080, etc., using the reaction conditions of Sonogashira coupling in the presence of, for example, tetrabutylammonium fluoride, the formula (VIb) [Wherein, R ⁶ has the same meaning as described above, and TMS represents trimethylsilyl or the like. By reacting with a substituted acetylene represented by the formula (I) wherein G ¹ , Y ¹ , Y ² , R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ are as defined above. Represent the same meaning. The present invention compound represented by the formula:

  Some of the compounds represented by the formula (V) used herein include, for example, International Patent Application Publication (WO 2014/177582), International Patent Application Publication (WO 2015/003951), and International Patent Application Publication ( WO 2015/004091), International Patent Application Publication (WO 2015/007626), International Patent Application Publication (WO 2015/078800), and others are known compounds. Can be synthesized in the same manner as described above.

  Some of the compounds represented by the formulas (VIa) and (VIb) are known compounds, and some of them are also available as commercial products. In addition, other compounds can be synthesized according to a general synthesis method described in a document relating to a known compound.

  In Production Methods A to C, the reaction mixture after completion of the reaction is directly concentrated, or dissolved in an organic solvent, and then subjected to ordinary post-treatments such as concentration after washing with water, or pouring into ice water, and concentration after extraction with an organic solvent. Can be obtained. When purification is necessary, separation and purification can be performed by any purification method such as recrystallization, column chromatography, thin-layer chromatography, or liquid chromatography.

  The compound represented by the formula (II) used in the production method A can be synthesized, for example, as shown in Reaction Formulas 1 and 2.

  Reaction formula 1

Formula (VII) [wherein, Y ¹ , Y ² , R ¹ , R ² , R ³ , R ⁴ , R ⁵ and J ³ represent the same meaning as described above. A compound represented by the formula (VIa) [wherein R ⁶ has the same meaning as described above, under the same reaction conditions as in Production method C]. Or a formula (VIb) wherein R ⁶ and TMS represent the same meaning as described above. By reacting with a substituted acetylene represented by the formula (VIII): wherein Y ¹ , Y ² , R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ have the same meaning as described above. Represent. ] Can be synthesize | combined.

The thus-obtained compound represented by the formula (VIII) is used, for example, in European Patent Publication (EP 1,574,511), International Patent Application Publication (WO 2008/021927), International Patent Application Publication (WO 2010 / No. 075200), and by reacting with hydrochloric acid, hydrobromic acid, trifluoroacetic acid or the like to remove the compound, the compound represented by the formula (II) [wherein Y ¹ , Y ² , R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ represent the same meaning as described above. Or a salt thereof (for example, hydrochloride, hydrobromide, trifluoroacetate, etc.) can be obtained.

  Reaction formula 2

In a production intermediate represented by the formula (VIII) of the reaction formula 1, a compound represented by the formula (VIIIa) wherein R ⁶ is trimethylsilyl [wherein Y ¹ , Y ² , R ¹ , R ² , R ³ , R ⁴ and R ⁵ has the same meaning as described above. Can be converted to a fluoride such as tetrabutylammonium fluoride according to the method described in, for example, Bioorganic and Medicinal Chemistry [Bioorg. Med. Chem.] 2004, 12, 371. By reacting with a base such as potassium carbonate according to the method described in, for example, Angevante Chemie International Edition [Angew. Chem. Int. Ed.] 2013, 52, 8134. Formula (VIIIb) [wherein Y ¹ , Y ² , R ¹ , R ² , R ³ , R ⁴ and R ⁵ represent the same meaning as described above. ] Can be synthesize | combined.

Then, the compound represented by the formula (VIIIb) is subjected to general Sonogashira coupling described in, for example, Journal of Organometallic Chemistry [J. Organomet. Chem.] 2006, 691, 975, and the like. Using reaction conditions, formula (IX) wherein R ⁶ represents phenyl substituted by (Z) _m and the aromatic heterocycle represented by D-1 to D-29, and J ³ is the same as defined above. Represent meaning. By reacting with a compound represented by the formula (VIII): wherein Y ¹ , Y ² , R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ have the same meaning as described above. . ] Can be synthesize | combined.

  In addition, the compound represented by the formula (VIIIa) can be used, for example, in the form of Organic Medicinal Chemistry Letters [ACS Med. Chem. Lett.] 2012, vol. 3, p. 544, Organic and Biomolecular Chemistry [Org Biomol. Chem.] 2015, vol. 13, p. 10852, etc., using the reaction conditions of Sonogashira coupling in the presence of, for example, tetrabutylammonium fluoride, and represented by the formula (IX). The compound represented by the formula (VIII) can be directly synthesized by reacting the compound with a compound represented by the formula (VIII).

The compound represented by the formula (VIII) thus obtained is deprotected in the same manner as in Reaction Scheme 1 to give a compound of the formula (II) [wherein Y ¹ , Y ² , R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ represent the same meaning as described above. Or a salt thereof (for example, hydrochloride, hydrobromide, trifluoroacetate, etc.) can be obtained.

  Some of the compounds represented by the formula (IX) used here are known compounds, and some of them are also available as commercial products. In addition, other compounds can be synthesized according to a general synthesis method described in a document relating to a known compound.

  The compound represented by Formula (VII) used in Reaction Scheme 1 can be synthesized, for example, as shown in Reaction Schemes 3 to 15.

  Reaction formula 3

Formula (X) [wherein, Y ¹ , Y ² and J ³ represent the same meaning as described above. And a compound represented by the formula (XI): wherein R ³ has the same meaning as described above. A known nitroalkane derivative represented by the following formula, for example, according to the method described in Journal of Medicinal Chemistry [J. Med. Chem.] 1992, 35, 734, etc. Formula (XII) wherein Y ¹ , Y ² , R ³ and J ³ represent the same meaning as described above. ] Can be synthesize | combined.

Then, the compound represented by the formula (XII) is reacted with sodium borohydride according to the method described in, for example, Synthetic Communications [Synth. Commun.] 1989, Vol. 19, p. (XIII) [wherein, Y ¹ , Y ² , R ³ and J ³ represent the same meaning as described above. After synthesizing a compound represented by the formula (1), for example, zinc-acetic acid is converted according to the method described in The Journal of Organic Chemistry [J. Org. Chem.] 2011, Vol. And reducing the compound with the formula (XIV) [wherein Y ¹ , Y ² , R ³ and J ³ represent the same meaning as described above. ] Can be synthesize | combined.

  Further, the compound represented by the formula (XII) can be converted to borohydride according to the method described in, for example, The Journal of Organic Chemistry [J. Org. Chem.] 1985, vol. By reducing borane in the presence of sodium, the compound represented by the formula (XIV) can also be directly synthesized.

The compound represented by the formula (XIV) thus obtained is described in, for example, Bioorganic and Medicinal Chemistry Letters [Bioorg. Med. Chem. Lett.] 2010, Vol. 20, p. 5822. By reacting with di-tert-butyl dicarbonate according to the method of formula (VIIa) wherein R ¹ , R ² , R ⁴ and R ⁵ in formula (VII) are hydrogen atoms, wherein Y ¹ , Y ² , R ³ and J ³ represent the same meaning as described above. ] Can be obtained.

  Some of the compounds represented by the formula (X) used here are known compounds, and some of them are also available as commercial products. In addition, other compounds can be synthesized according to a general synthesis method described in a document relating to a known compound.

  Reaction formula 4

Formula (XII) of Reaction Scheme 3 [wherein Y ¹ , Y ² , R ³ and J ³ represent the same meaning as described above. By subjecting the synthetic intermediate represented by the formula (XV) [wherein Y ¹ , Y ² to the iron reduction according to the method described in, for example, International Patent Application Publication (WO 2008/052733) and the like. , R ³ and J ³ represent the same meaning as described above. ] Can be synthesize | combined.

Then, a compound represented by the formula (XV) and a compound represented by the formula (XVI): wherein R ⁵ is C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₃ -C ₄ cycloalkyl, C ₁ -C ₄ Represents alkoxy, C ₁ -C ₄ haloalkoxy and the like. With sodium cyanoborohydride, for example, according to the method described in European Journal of Medicinal Chemistry [Eur. J. Med. Chem.] 2009, 44, 4862, etc. By reacting in the presence of a reducing agent such as, for example, formula (XVII) [wherein Y ¹ , Y ² , R ³ , R ⁵ and J ³ represent the same meaning as described above. ] Can be synthesize | combined.

The compound represented by the formula (XVII) thus obtained can be used, for example, in International Patent Application Publication (WO 2005/054238), Journal of the American Chemical Society [J. Am. Chem. Soc.], 2007, vol. 129, p. 347, etc., whereby R ¹ , R ² and R ⁴ in the formula (VII) are hydrogen atoms by reacting with di-tert-butyl dicarbonate. Formula (VIIb) wherein Y ¹ , Y ² , R ³ , R ⁵ and J ³ represent the same meaning as described above. ] Can be obtained.

  Some of the compounds represented by the formula (XVI) used here are known compounds, and some of them are also available as commercial products. In addition, other compounds can be synthesized according to a general synthesis method described in a document relating to a known compound.

  Reaction formula 5

Formula (XV) in Reaction Scheme 4, wherein Y ¹ , Y ² , R ³ and J ³ represent the same meaning as described above. Wherein R ¹ is substituted by C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, phenyl (C ₁ -C ₄ ) alkyl, (Z) _m phenyl _(C 1 _{~C 4)} alkyl, C ₃ -C ₆ cycloalkyl, C ₂ -C ₆ alkenyl represents a C ₂ -C ₆ alkynyl and the like. With a compound represented by the formula (XIX) [wherein Y ¹ is represented by the following formula: Tetrahedron: Asymmetry], 2009, Vol. 20, p. 1168. , Y ² , R ¹ , R ³ and J ³ represent the same meaning as described above. ] Can be synthesize | combined.

Then, the compound represented by the formula (XIX) is reacted with sodium cyanoborohydride or the like in the presence of an amine source such as ammonium acetate according to a method described in, for example, International Patent Application Publication (WO 2011/124093). By reacting with a reducing agent of the formula (XX) wherein Y ¹ , Y ² , R ¹ , R ³ and J ³ have the same meaning as described above. ] Can be synthesize | combined.

The thus-obtained compound represented by the formula (XX) is reacted with di-tert-butyl dicarbonate in the same manner as in the reaction formula 3 to obtain R ² , R ⁴ and R ⁵ in the formula (VII). Is a hydrogen atom of the formula (VIIc) wherein Y ¹ , Y ² , R ¹ , R ³ and J ³ represent the same meaning as described above. ] Can be obtained.

  Some of the compounds represented by the formula (XVIII) used here are known compounds, and some of them are also available as commercial products. In addition, other compounds can be synthesized according to a general synthesis method described in a document relating to a known compound.

  Reaction formula 6

Formula (XII) of Reaction Scheme 3 [wherein Y ¹ , Y ² , R ³ and J ³ represent the same meaning as described above. And a synthetic intermediate represented by the formula (XXI) [wherein W represents an oxygen atom, a sulfur atom or -NHO-, ^Ra is C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl, represents a _(Z) phenyl substituted by _{m (C} 1 ~C ₄₎ alkyl and the like. Known alcohols, thiols or alkoxyamines represented by, for example, Tetrahedron, Journal of Chemical Research Synopses [J. Chem. Res. (S)] 1982, p. 156, tetrahedron [Tetrahedron]. 2003, vol. 59, p. 2417, European Journal of Organic Chemistry [Eur. J. Org. Chem.] 2010, p. Wherein Y ¹ , Y ² , W, ^Ra , R ³ and J ³ represent the same meaning as described above. ] Can be synthesize | combined.

Then, the compound represented by the formula (XXII) is prepared by the method described in, for example, Bulletin of the Chemical Society of Japan [Bull. Chem. Soc. Jpn.] 2014, Vol. 87, p. Reduction using zinc-acetic acid according to the method described in, for example, Cobalt chloride (J. Org. Chem.) 2014, Vol. 79, p. 6913, etc. I) Reduction using sodium borohydride in the presence gives a compound of the formula (XXIII) wherein Y ¹ , Y ² , W, ^Ra , R ³ and J ³ have the same meaning as described above. ] Can be synthesize | combined.

The thus-obtained compound represented by the formula (XXIII) is reacted with di-tert-butyl dicarbonate in the same manner as in the reaction formula 3 to obtain R ² , R ⁴ and R ⁵ in the formula (VII). Is a hydrogen atom of the formula (VIId) wherein Y ¹ , Y ² , W, ^Ra , R ³ and J ³ represent the same meaning as described above. ] Can be obtained.

  Reaction formula 7

Formula (XXIV) [wherein Y ¹ , Y ² , R ³ and J ³ represent the same meaning as described above. For example, a method described in The Journal of Organic Chemistry [J. Org. Chem.] 1982, 47, 2795, etc. -Hemy International Edition [Angew. Chem. Int. Ed.] 2009, vol. 48, p. 154, etc., by halogenating using a method of reacting with bromine according to the method, etc. XXV) [wherein, Y ¹ , Y ² , R ³ and J ³ represent the same meaning as described above, and J ⁴ represents a chlorine atom, a bromine atom and the like. And then reacting with sodium azide according to the method described in, for example, The Journal of Organic Chemistry [J. Org. Chem.] 1989, vol. 54, p. 431. In this case, Y ¹ , Y ² , R ³ and J ³ represent the same meaning as described above. ] Can be synthesize | combined.

Next, the compound represented by the formula (XXVI) is reacted with zinc-aluminum chloride according to the method described in, for example, International Patent Application Publication (WO 2012/020738) and the like. By reacting with -tert-butyl, the compound represented by the formula (XXVII) [wherein Y ¹ , Y ² , R ³ and J ³ represent the same meaning as described above. ] Can be synthesize | combined.

The compound represented by the formula (XXVII) thus obtained is reduced using sodium borohydride or the like according to a method described in, for example, International Patent Application Publication (WO 2004/022568). Is represented by the formula (XXVIII) [wherein Y ¹ , Y ² , R ³ and J ³ represent the same meaning as described above. And then fluorinated according to the method described in, for example, The Journal of Organic Chemistry [J. Org. Chem.] 2009, vol. 74, p. 2609. Wherein in formula (VII), R ¹ represents a fluorine atom and R ² , R ⁴ and R ⁵ are hydrogen atoms, wherein Y ¹ , Y ² , R ³ and J ³ are the same as above Represent meaning. ] Can be obtained.

  Some of the compounds represented by the formula (XXIV) used here are known compounds, and some of them are also available as commercial products. In addition, other compounds can be synthesized according to a general synthesis method described in a document relating to a known compound.

  Reaction formula 8

Formula (XXVII) of Reaction Scheme 7, wherein Y ¹ , Y ² , R ³ and J ³ represent the same meaning as described above. The synthetic intermediate represented by, for example, Bioorganic and Medicinal Chemistry Letters [Bioorg. Med. Chem. Lett.] 1996, 6, 1875, International Patent Application Publication (WO 2014/184365). Publication), fluorination according to the method described in formula (VIIf) wherein R ¹ and R ² in the formula (VII) represent a fluorine atom, and R ⁴ and R ⁵ are hydrogen atoms. Y ¹ , Y ² , R ³ and J ³ represent the same meaning as described above. ] Can be obtained.

  Reaction formula 9

Formula (XXVII) of Reaction Scheme 7, wherein Y ¹ , Y ² , R ³ and J ³ represent the same meaning as described above. The intermediate represented by the formula (XXIX) [formula (XXIX)] according to the method described in, for example, Angevante Chemie International Edition [Angew. Chem. Int. Ed.] 2014, 53, 3913. In the formula, R ¹ represents C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, etc., and J ⁵ represents a chlorine atom, a bromine atom or an iodine atom. By reacting with a known Grignard reactant represented by the formula (XXX) wherein Y ¹ , Y ² , R ¹ , R ³ and J ³ have the same meaning as described above. ] Can be synthesize | combined.

By fluorinating the thus-obtained compound represented by the formula (XXX) according to a method described in, for example, International Patent Application Publication (WO 2012/125887), the compound represented by the formula (VII) Formula (VIIg) wherein R ² represents a fluorine atom and R ⁴ and R ⁵ are hydrogen atoms, wherein Y ¹ , Y ² , R ¹ , R ³ and J ³ have the same meanings as described above. ] Can be obtained.

  Reaction formula 10

Formula (XXXI) [wherein, Y ¹ , Y ² and J ³ represent the same meaning as described above, and R ¹ and R ² each independently represent methyl, ethyl and the like. After reaction with diisobutylaluminum hydride according to the method described in, for example, The Journal of Organic Chemistry [J. Org. Chem.] 1984, 49, 3069. By hydrolysis, the compound represented by the formula (XXXII) [wherein Y ¹ , Y ² , R ¹ , R ² and J ³ represent the same meaning as described above. ] Can be synthesize | combined.

Further, the compound represented by the formula (XXXII) is converted to a compound represented by the formula (XXXIII) [wherein R ³ is the same as that described in, for example, Tetrahedron Lett., 1989, Vol. 30, p. 3561. Represents a C ₁ -C ₆ alkyl and the like, and J ⁵ represents the same meaning as described above. Or a known Grignard reactant represented by the formula (XXXIV) [Formula (XXXIV) [Formula XXXIV] according to the method described in Helvetica Chimica Acta 2002, Vol. 85, p. In the formula, R ³ represents C ₁ -C ₆ alkyl and the like. By reacting with a known alkyllithium reactant represented by the formula (XXXV): wherein Y ¹ , Y ² , R ¹ , R ² , R ³ and J ³ have the same meaning as described above. ] Can be synthesize | combined.

Then, the compound represented by the formula (XXXV) is converted to methanesulfonyl chloride according to the method described in, for example, European Journal of Organic Chemistry [Eur. J. Org. Chem.] 2013, p. 6924, and the like. The reaction is carried out by reacting a compound of the formula (XXXVI) wherein Y ¹ , Y ² , R ¹ , R ² , R ³ and J ³ have the same meaning as described above. And then reacting with sodium azide according to the method described in, for example, Journal of Medicinal Chemistry [J. Med. Chem.] 2006, 49, 7584. In Formula (XXXVII), Y ¹ , Y ² , R ¹ , R ² , R ³ and J ³ represent the same meaning as described above. ] Can be synthesize | combined.

The compound represented by the formula (XXXVII) thus obtained is reacted with triphenylphosphine according to the method described in, for example, Organic Letters [Organic. Lett.] 2010, Vol. 12, p. 2936. And then treated with water to obtain a compound of the formula (XXXVIII) wherein Y ¹ , Y ² , R ¹ , R ² , R ³ and J ³ have the same meaning as described above. And then reacting it with di-tert-butyl dicarbonate in the same manner as in Reaction Scheme 3, or converting the compound represented by the formula (XXXVII) into, for example, Bioorganic and Medicinal. Chemistry Letters [Bioorg. Med. Chem. Lett.] 2010, vol. 20, p. 4747, etc., using platinum (IV) oxide as a catalyst in the presence of di-tert-butyl dicarbonate as a catalyst. By addition, a compound represented by the formula (VIIh) wherein R ⁴ and R ⁵ are hydrogen atoms in the formula (VII) [wherein Y ¹ , Y ² , R ¹ , R ² , R ³ and J ³ have the same meanings as described above. Represents ] Can be obtained.

  Some of the compounds represented by the formula (XXXI) used here are known compounds, and some of them are also available as commercial products. In addition, other compounds can be synthesized according to a general synthesis method described in a document relating to a known compound.

  Reaction formula 11

Formula (XXXI) [wherein Y ¹ , Y ² and J ³ represent the same meaning as described above, and R ¹ and R ² represent a fluorine atom, or R ¹ and R ² together form ethylene. Forming a chain indicates that R ¹ and R ² form a cyclopropyl ring together with the carbon atom to which they are attached. The compound represented by the formula (XXXIII) [wherein, for example, the method described in Australian Journal of Chemistry [Aust. J. Chem.] 1990, 43, 2045, etc.] R ³ and J ⁵ represent the same meaning as described above. And reacting with a known Grignard reagent represented by the formula (XXXVIII) [wherein Y ¹ , Y ² , R ¹ , R ² , R ³ and J ³ are as defined above. ] Can be synthesize | combined.

The thus-obtained compound represented by the formula (XXXVIII) is reacted with di-tert-butyl dicarbonate in the same manner as in the reaction formula 3, whereby R ⁴ and R ⁵ in the formula (VII) are hydrogen. An atom represented by the formula (VIIh): wherein Y ¹ , Y ² , R ¹ , R ² , R ³ and J ³ represent the same meaning as described above. ] Can be obtained.

  Some of the compounds represented by the formula (XXXI) used here are known compounds, and some of them are also available as commercial products. In addition, other compounds can be synthesized according to a general synthesis method described in a document relating to a known compound.

  Reaction formula 12

Formula (XXXIX) [wherein, Y ¹ , Y ² and J ³ represent the same meaning as described above, and R ^b represents C ₁ -C ₆ alkyl. A compound represented by, for example, International Patent Application Publication (WO 2012/125613 discloses) the formula (XL) [in the formula according to the method described in such as, J ⁵ are as defined above. By reacting with a known Grignard reagent represented by the formula (XLI) wherein Y ¹ , Y ² and J ³ have the same meanings as described above. ] Can be synthesize | combined.

Next, the compound represented by the formula (XLI) was synthesized using, for example, Bioorganic and Medicinal Chemistry Letters [Bioorg. Med. Chem. Lett.] 2009, 19, 6640, Synthesis 2000, According to the method described on page 1709 and the like, in the presence of a strong acid such as sulfuric acid, the known formula (XLII) [wherein R ^c represents methyl, chloromethyl or the like. And a nitrile compound represented by the formula (XLIII): wherein Y ¹ , Y ² , R ^c and J ³ have the same meaning as described above. And then reacting with a strong base such as potassium hydroxide or thiourea-acetic acid to obtain a compound of the formula (XLIV) wherein Y ¹ , Y ² and J ³ have the same meanings as described above. . ] Can be synthesize | combined.

The thus-obtained compound represented by the formula (XLIV) is reacted with di-tert-butyl dicarbonate according to a method described in, for example, International Patent Application Publication (WO 2006/051373). In Formula (VII), R ¹ , R ² and R ⁵ are hydrogen atoms, and R ³ and R ⁴ are methyl, wherein Y ¹ , Y ² and J ³ are the same as above. Represent meaning. ] Can be obtained.

  Some of the compounds represented by the formula (XXXIX) used here are known compounds, and some of them are also available as commercial products. In addition, other compounds can be synthesized according to a general synthesis method described in a document relating to a known compound.

  Reaction formula 13

Formula (XLV) wherein Y ¹ , Y ² and J ³ represent the same meaning as described above. The compound represented by the following formula: Chemical Communications [Chem. Commun.] 2001, p. 1792, Synthesis [2007], p. 131, etc. according to the method described in titanium (IV) tetraisopropoxide. By reacting with lower ethylmagnesium bromide and subsequently with a boron trifluoride etherate complex, formula (XLVI) [wherein Y ¹ , Y ² and J ³ represent the same meaning as described above. ] Can be synthesize | combined.

The thus-obtained compound represented by the formula (XLVI) is reacted with di-tert-butyl dicarbonate according to a method described in, for example, International Patent Application Publication (WO 2003/099276). According to the formula (VIIj), R ¹ , R ² and R ⁵ in the formula (VII) are hydrogen atoms, and together with the carbon atom to which R ³ and R ⁴ are bonded, a cyclopropyl ring is formed. , Y ¹ , Y ² and J ³ represent the same meaning as described above. ] Can be obtained.

  Some of the compounds represented by the formula (XLV) used here are known compounds, and some of them are also available as commercial products. In addition, other compounds can be synthesized according to a general synthesis method described in a document relating to a known compound.

  Reaction formula 14

Formula (XXXI) [wherein, Y ¹ , Y ² and J ³ represent the same meaning as described above, R ¹ represents a fluorine atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy, etc., and R ² represents Represents a hydrogen atom, a fluorine atom, a C ₁ -C ₆ alkyl, etc., or R ¹ and R ² together form an ethylene chain to form a cyclo with a carbon atom to which R ¹ and R ² are bonded. Represents that a propyl ring is formed. Compounds represented by, for example, Journal of Medicinal Chemistry [J. Med. Chem.] 2009, 52, 4613, Synthetic Communications [Synth. Commun.] 2004, 34, 2463. International Patent Application Publication (WO 2007/134862), International Patent Application Publication (WO 2011/124093), The Journal of Organic Chemistry [J. Org. Chem.] 1996, Vol. 61, 185, Bioorganic and Medicinal Chemistry [Bioorg. Med. Chem.] 2007, 15, 7677, Letters in Organic Chemistry [Lett. Org. Chem.] 2015, 12, 222. Borane-tetrahydrofuran complex, borane-dimethylsulfide complex, sodium borohydride-cellulose chloride according to the method described in By reduction using a beam (III) mixtures of formula (XLVII) ^{[wherein, Y 1, Y 2, R} 1, R 2 and J ³ are as defined above. ] Can be synthesize | combined.

The compound represented by the formula (XLVII) thus obtained is described in, for example, Bioorganic and Medicinal Chemistry Letters [Bioorg. Med. Chem. Lett.] 2012, Vol. 22, p. 6108. By reacting with di-tert-butyl dicarbonate according to the method of formula (VIIk) wherein R ³ , R ⁴ and R ⁵ are hydrogen atoms in formula (VII) [wherein Y ¹ , Y ² , R ¹ , R ² and J ³ represent the same meaning as described above. ] Can be obtained.

  Some of the compounds represented by the formula (XXXI) used here are known compounds, and some of them are also available as commercial products. In addition, other compounds can be synthesized according to a general synthesis method described in a document relating to a known compound.

  Reaction formula 15

Formula (XLVIII) wherein Y ¹ , Y ² and J ³ represent the same meaning as described above. Is reduced using a borane-tetrahydrofuran complex, a borane-dimethylsulfide complex or the like in the same manner as in Reaction Scheme 14, and then reacted with di-tert-butyl dicarbonate to obtain a compound represented by the formula (VII). In formula (VIIm), R ¹ and R ² are each a fluorine atom, and R ³ , R ⁴ and R ⁵ are each a hydrogen atom, wherein Y ¹ , Y ² and J ³ have the same meanings as described above. ] Can be obtained.

  The compound represented by the formula (XLVIII) used here can be synthesized, for example, as follows.

  Reaction formula 16

That is, the known formula (L) wherein Y ¹ and Y ² represent the same meaning as described above. And a known formula (LI) wherein R ^b represents the same meaning as described above, and J ⁶ represents a bromine atom, an iodine atom, trimethylsilyl, or the like. A compound represented by the formula: Bioorganic and Medicinal Chemistry Letters [Bioorg. Med. Chem. Lett.] 2008, Vol. 18, p. 2865, using copper. Or by using a copper (I) iodide-potassium fluoride system according to the method described in Organic Letters [Organic. Lett.] 2011, Vol. 13, p. 5560, for example. Formula (LII) [wherein Y ¹ , Y ² and ^Rb represent the same meaning as described above. ] Can be synthesize | combined.

The thus-obtained compound represented by the formula (LII) is subjected to a method described in, for example, The Journal of Organic Chemistry [J. Org. Chem.] 1980, Vol. 45, p. Accordingly, by reacting with ammonia in a solvent such as methanol or ethanol, a compound represented by the formula (XLVIIIa) wherein R ¹ and R ² are a fluorine atom and J ³ is a bromine atom in the formula (XLVIII) [wherein Y ¹ And Y ² represent the same meaning as described above. ] Can be obtained.

Further, the compound represented by the formula (XLVIIIa) can be obtained by reacting trifluoroacetic anhydride or the like in the presence of a base such as pyridine or triethylamine according to the method described in, for example, International Patent Application Publication (WO 2006/017409). By dehydration using the formula (XXXI), the formula (XXXIa) wherein R ¹ and R ² are a fluorine atom and J ³ is a bromine atom, wherein Y ¹ and Y ² have the same meanings as described above. . To the compound represented by the formula:

  In each of these reactions, after the completion of the reaction, each of the production intermediates to be the starting compounds of Production Methods A to C can be obtained by performing ordinary post-treatments.

  In addition, each intermediate produced by these methods can be directly used in the next step reaction without isolation and purification.

  Specific examples of the alkynylphenyl-substituted amide compound represented by the formula (I) included in the present invention which can be produced by using these methods include, for example, the following structural formulas [I] -1 to [I] -14: The compound represented by these is mentioned. However, the compounds represented by the structural formulas [I] -1 to [I] -14 are for illustration only, and the alkynylphenyl-substituted amide compounds included in the present invention are not limited thereto. is not.

Here, specific examples of the substituents represented by Y ¹ , Y ² , R ¹ , R ² , R ³ , R ⁴ and R ⁶ in the structural formulas [I] -1 to [I] -30 Examples of the combination include, for example, the combinations shown in Table 2. However, the combinations in Table 2 are for the purpose of illustration, and the alkynylphenyl-substituted amide compounds included in the present invention are represented by Y ¹ , Y ² , R ¹ , R ² , R ³ , R ⁴ and R ⁶ . Specific combinations of the substituents represented are not limited to these.

In the table, the description of Et represents ethyl, n-Pr represents normal propyl, i-Pr and Pr-i represent isopropyl, c-Pr represents cyclopropyl, and Bu-s represents sec-. Butyl, c-Bu represents cyclobutyl, t-Bu and Bu-t represent tert-butyl, c-Pen represents cyclopentyl, c-Hex represents cyclohexyl, Ph represents phenyl,
In the table, the aromatic heterocycles represented by D-1-1a to D-26-1c respectively represent the following structures,

The number representing the substitution position of the substituent (Z) _n corresponds to the position of the number described in the above structural formula, and for example, in the table, `` (D-23-2b) -6- The description "F" represents "6-fluoropyridin-3-yl",
In the table, T-1 to T-14 represent the following structures, respectively.

  In the table, the substituent R¹And the substituent R³Notation of (R) and (S) in the column of¹Or R³Represents that the ratio of the (R) -isomer or the (S) -isomer is 90% or more in the mixing ratio of the optical isomer of the carbon atom to which is bonded.
Table 2
――――――――――――――――――――――――――――――――――――――――
R^Three        R^Four         R¹         R^Two         Y¹             R⁶              Y^Two
――――――――――――――――――――――――――――――――――――――――
H H H H Cl CH_Three             H
H H H H Cl c-Pr H
H H H H Cl t-Bu H
H H H H Cl C (CH_Three)_TwoF H
H H H H Cl Si (CH_Three)_Three           H
H H H H Cl Ph-2-F H
H H H H Cl Ph-3-F H
H H H H Cl Ph-4-F H
H H H H Cl (D-2-1b) -5-F H
H H H H Cl (D-8-2b) -2-CH_Three        H
H H H H Cl (D-23-1b) -5-CF_Three       H
H H H H Cl (D-23-2b) -6-F H
H H H H Cl (D-23-2b) -6-Cl H
H H H H Cl (D-23-2b) -6-CF_Three       H
H H F H Cl CH_Three             H
H H F H Cl c-Pr H
H H F H Cl t-Bu H
H H F H Cl C (CH_Three)_TwoF H
H H F H Cl Si (CH_Three)_Three           H
H H F H Cl Ph-2-F H
H H F H Cl Ph-3-F H
H H F H Cl Ph-4-F H
H H F H Cl (D-2-1b) -5-F H
H H F H Cl (D-8-2b) -2-CH_Three        H
H H F H Cl (D-23-1b) -5-CF_Three       H
H H F H Cl (D-23-2b) -6-F H
H H F H Cl (D-23-2b) -6-Cl H
H H F H Cl (D-23-2b) -6-CF_Three       H
H H F F Cl CH_Three             H
H H F F Cl c-Pr H
H H F F Cl t-Bu H
H H F F Cl C (CH_Three)_TwoF H
H H F F Cl Si (CH_Three)_Three           H
H H F F Cl Ph-2-F H
H H F F Cl Ph-3-F H
H H F F Cl Ph-4-F H
H H F F Cl D-1-2a H
H H F F Cl (D-1-2b) -2-F H
H H F F Cl (D-1-2b) -2-CH_Three        H
H H F F Cl (D-1-2b) -4-CH_Three        H
H H F F Cl (D-1-2b) -5-CH_Three        H
H H F F Cl D-1-2c H
H H F F Cl (D-2-1b) -5-F H
H H F F Cl D-2-2a H
H H F F Cl (D-2-2b) -2-F H
H H F F Cl (D-2-2b) -4-F H
H H F F Cl (D-2-2b) -5-F H
H H F F Cl (D-2-2b) -5-Cl H
H H F F Cl (D-2-2b) -5-CH_Three        H
H H F F Cl (D-2-2b) -5-OCH_Three       H
H H F F Cl (D-2-2b) -5-CN H
H H F F Cl D-2-2c H
H H F F Cl (D-8-2b) -2-CH_Three        H
H H F F Cl D-23-1a H
H H F F Cl (D-23-1b) -3-F H
H H F F Cl (D-23-1b) -4-Cl H
H H F F Cl (D-23-1b) -4-CH_Three       H
H H F F Cl (D-23-1b) -4-CF_Three       H
H H F F Cl (D-23-1b) -5-F H
H H F F Cl (D-23-1b) -5-CH_Three       H
H H F F Cl (D-23-1b) -5-CF_Three       H
H H F F Cl (D-23-1b) -5-OCF_Three       H
H H F F Cl (D-23-1b) -5-CN H
H H F F Cl (D-23-1b) -6-F H
H H F F Cl (D-23-1b) -6-Cl H
H H F F Cl (D-23-1b) -6-CH_Three       H
H H F F Cl (D-23-1b) -6-CF_Three       H
H H F F Cl (D-23-1b) -6-OCH_Three       H
H H F F Cl (D-23-1b) -4,5-F_Two       H
H H F F Cl (D-23-1b) -4,5-Cl_Two      H
H H F F Cl (D-23-1b) -4-CH_Three-5-F H
H H F F Cl (D-23-1b) -3-F-5-CH_Three     H
H H F F Cl (D-23-1b) -5-F-6-CH_Three     H
H H F F Cl (D-23-1b) -4-CH_Three-5-Cl H
H H F F Cl (D-23-1b) -5-Cl-6-CH_Three     H
H H F F Cl (D-23-1b) -4-CF_Three-5-F H
H H F F Cl (D-23-1b) -3-F-5-CF_Three     H
H H F F Cl (D-23-1b) -5-F-6-CF_Three     H
H H F F Cl (D-23-1b) -3-CF_Three-5-Cl H
H H F F Cl (D-23-1b) -4-CF_Three-5-Cl H
H H F F Cl (D-23-1b) -5-Cl-6-CF_Three     H
H H F F Cl (D-23-1b) -5-CF_Three-6-CH_Three    H
H H F F Cl (D-23-1b) -4-OCH_Three-5-Cl H
H H F F Cl (D-23-1b) -5-Cl-6-OCH_Three    H
H H F F Cl (D-23-1b) -5-CF_Three-6-OCH_Three    H
H H F F Cl D-23-1c H
H H F F Cl D-23-1d H
H H F F Cl D-23-2a H
H H F F Cl (D-23-2b) -2-F H
H H F F Cl (D-23-2b) -5-F H
H H F F Cl (D-23-2b) -5-Cl H
H H F F Cl (D-23-2b) -5-CH_Three       H
H H F F Cl (D-23-2b) -5-OCH_Three       H
H H F F Cl (D-23-2b) -6-F H
H H F F Cl (D-23-2b) -6-Cl H
H H F F Cl (D-23-2b) -6-CH_Three       H
H H F F Cl (D-23-2b) -6-CF_Three       H
H H F F Cl (D-23-2b) -6-OCH_Three       H
H H F F Cl (D-23-2b) -6-CN H
H H F F Cl (D-23-2b) -4,6-F_Two       H
H H F F Cl (D-23-2b) -4-F-6-Cl H
H H F F Cl (D-23-2b) -5-F-6-CH_Three     H
H H F F Cl (D-23-2b) -5-Cl-6-CH_Three     H
H H F F Cl (D-23-2b) -5-F-6-CF_Three     H
H H F F Cl (D-23-2b) -5-Cl-6-CF_Three     H
H H F F Cl (D-23-2b) -5-CH_Three-6-CF_Three    H
H H F F Cl (D-23-2b) -4-F-6-OCH_Three     H
H H F F Cl (D-23-2b) -5-F-6-OCH_Three     H
H H F F Cl (D-23-2b) -5-OCH_Three-6-CF_Three    H
H H F F Cl (D-23-2b) -5-CF_Three-6-OCH_Three    H
H H F F Cl (D-23-2b) -5-F-6-OCF_Three     H
H H F F Cl D-23-2c H
H H F F Cl D-23-2d H
H H F F Cl D-23-2e H
H H F F Cl D-23-2f H
H H F F Cl D-23-2g H
H H F F Cl D-25-3a H
H H F F Cl (D-25-3b) -2-Cl H
H H F F Cl (D-25-3b) -2-CH_Three       H
H H F F Cl (D-25-3b) -2-OCH_Three       H
H H CH_Three        H Cl CH_Three             H
H H CH_Three        H Cl c-Pr H
H H CH_Three        H Cl t-Bu H
H H CH_Three        H Cl C (CH_Three)_TwoF H
H H CH_Three        H Cl Si (CH_Three)_Three           H
H H CH_Three        H Cl Ph-2-F H
H H CH_Three        H Cl Ph-3-F H
H H CH_Three        H Cl Ph-4-F H
H H CH_Three        H Cl (D-2-1b) -5-F H
H H CH_Three        H Cl (D-8-2b) -2-CH_Three        H
H H CH_Three        H Cl (D-23-1b) -5-CF_Three       H
H H CH_Three        H Cl (D-23-2b) -6-F H
H H CH_Three        H Cl (D-23-2b) -6-Cl H
H H CH_Three        H Cl (D-23-2b) -6-CF_Three       H
H H -CH_TwoCH_Two-Cl CH_Three             H
H H -CH_TwoCH_Two-Cl c-Pr H
H H -CH_TwoCH_Two-Cl t-Bu H
H H -CH_TwoCH_Two-Cl C (CH_Three)_TwoF H
H H -CH_TwoCH_Two-Cl Si (CH_Three)_Three           H
H H -CH_TwoCH_Two-Cl Ph-2-F H
H H -CH_TwoCH_Two-Cl Ph-3-F H
H H -CH_TwoCH_Two-Cl Ph-4-F H
H H -CH_TwoCH_Two-Cl (D-2-1b) -5-F H
H H -CH_TwoCH_Two-Cl (D-8-2b) -2-CH_Three        H
H H -CH_TwoCH_Two-Cl (D-23-1b) -5-CF_Three       H
H H -CH_TwoCH_Two-Cl (D-23-2b) -6-F H
H H -CH_TwoCH_Two-Cl (D-23-2b) -6-Cl H
H H -CH_TwoCH_Two-Cl (D-23-2b) -6-CF_Three       H
H H OCH_Three        H Cl CH_Three             H
H H OCH_Three        H Cl c-Pr H
H H OCH_Three        H Cl t-Bu H
H H OCH_Three        H Cl C (CH_Three)_TwoF H
H H OCH_Three        H Cl Si (CH_Three)_Three           H
H H OCH_Three        H Cl Ph-2-F H
H H OCH_Three        H Cl Ph-3-F H
H H OCH_Three        H Cl Ph-4-F H
H H OCH_Three        H Cl (D-2-1b) -5-F H
H H OCH_Three        H Cl (D-8-2b) -2-CH_Three        H
H H OCH_Three        H Cl (D-23-1b) -5-CF_Three       H
H H OCH_Three        H Cl (D-23-2b) -6-F H
H H OCH_Three        H Cl (D-23-2b) -6-Cl H
H H OCH_Three        H Cl (D-23-2b) -6-CF_Three       H
CH_Three       H H H F CH_Three             H
CH_Three       H H H F CH_Three             F
CH_Three       H H H F Et H
CH_Three       H H H F Et F
CH_Three       H H H F n-Pr H
CH_Three       H H H F n-Pr F
CH_Three       H H H F i-Pr H
CH_Three       H H H F i-Pr F
CH_Three       H H H F c-Pr H
CH_Three       H H H F c-Pr F
CH_Three       H H H F T-2 H
CH_Three       H H H F T-2 F
CH_Three       H H H F c-Bu H
CH_Three       H H H F c-Bu F
CH_Three       H H H F t-Bu H
CH_Three       H H H F t-Bu F
CH_Three       H H H F T-1 H
CH_Three       H H H F T-1 F
CH_Three       H H H F CH_TwoF H
CH_Three       H H H F CH_TwoF F
CH_Three       H H H F C (CH_Three)_TwoF H
CH_Three       H H H F C (CH_Three)_TwoF F
CH_Three       H H H F T-4 H
CH_Three       H H H F T-4 F
CH_Three       H H H F T-5 H
CH_Three       H H H F T-5 F
CH_Three       H H H F T-6 H
CH_Three       H H H F T-6 F
CH_Three       H H H F T-7 H
CH_Three       H H H F T-7 F
CH_Three       H H H F T-13 H
CH_Three       H H H F T-13 F
CH_Three       H H H F CH_TwoOCH_Three           H
CH_Three       H H H F CH_TwoOCH_Three           F
CH_Three       H H H F C (CH_Three)_TwoOCH_Three         H
CH_Three       H H H F C (CH_Three)_TwoOCH_Three         F
CH_Three       H H H F Si (CH_Three)_Three           H
CH_Three       H H H F Si (CH_Three)_Three           F
CH_Three       H H H F Ph-2-F H
CH_Three       H H H F Ph-2-F F
CH_Three       H H H F Ph-3-F H
CH_Three       H H H F Ph-3-F F
CH_Three       H H H F Ph-4-F H
CH_Three       H H H F Ph-4-F F
CH_Three       H H H F Ph-3-Cl H
CH_Three       H H H F Ph-3-Cl F
CH_Three       H H H F Ph-4-Cl H
CH_Three       H H H F Ph-4-Cl F
CH_Three       H H H F Ph-2-CH_Three           H
CH_Three       H H H F Ph-2-CH_Three           F
CH_Three       H H H F Ph-3-CH_Three           H
CH_Three       H H H F Ph-3-CH_Three           F
CH_Three       H H H F Ph-4-CH_Three           H
CH_Three       H H H F Ph-4-CH_Three           F
CH_Three       H H H F Ph-2-CF_Three           H
CH_Three       H H H F Ph-2-CF_Three           F
CH_Three       H H H F Ph-3-CF_Three           H
CH_Three       H H H F Ph-3-CF_Three           F
CH_Three       H H H F Ph-4-CF_Three           H
CH_Three       H H H F Ph-4-CF_Three           F
CH_Three       H H H F Ph-3-OCH_Three          H
CH_Three       H H H F Ph-3-OCH_Three          F
CH_Three       H H H F Ph-4-OCH_Three          H
CH_Three       H H H F Ph-4-OCH_Three          F
CH_Three       H H H F Ph-4-OCF_Three          H
CH_Three       H H H F Ph-4-OCF_Three          F
CH_Three       H H H F Ph-4-CN H
CH_Three       H H H F Ph-4-CN F
CH_Three       H H H F Ph-2,4-F_Two          H
CH_Three       H H H F Ph-2,4-F_Two          F
CH_Three       H H H F Ph-3,4-F_Two          H
CH_Three       H H H F Ph-3,4-F_Two          F
CH_Three       H H H F Ph-3-Cl-4-F H
CH_Three       H H H F Ph-3-Cl-4-F F
CH_Three       H H H F Ph-2-F-4-Cl H
CH_Three       H H H F Ph-2-F-4-Cl F
CH_Three       H H H F Ph-3-F-4-Cl H
CH_Three       H H H F Ph-3-F-4-Cl F
CH_Three       H H H F Ph-3,4-Cl_Two          H
CH_Three       H H H F Ph-3,4-Cl_Two          F
CH_Three       H H H F Ph-3-F-4-OCF_Three        H
CH_Three       H H H F Ph-3-F-4-OCF_Three        F
CH_Three       H H H F (D-2-1b) -5-F H
CH_Three       H H H F (D-2-1b) -5-F F
CH_Three       H H H F D-8-2a H
CH_Three       H H H F D-8-2a F
CH_Three       H H H F (D-8-2b) -2-CH_Three        H
CH_Three       H H H F (D-8-2b) -2-CH_Three        F
CH_Three       H H H F (D-8-2b) -5-CH_Three        H
CH_Three       H H H F (D-8-2b) -5-CH_Three        F
CH_Three       H H H F (D-23-1b) -5-CF_Three       H
CH_Three       H H H F (D-23-1b) -5-CF_Three       F
CH_Three       H H H F (D-23-2b) -6-F H
CH_Three       H H H F (D-23-2b) -6-F F
CH_Three       H H H F (D-23-2b) -6-Cl H
CH_Three       H H H F (D-23-2b) -6-Cl F
CH_Three       H H H F (D-23-2b) -6-CH_Three       H
CH_Three       H H H F (D-23-2b) -6-CH_Three       F
CH_Three       H H H F (D-23-2b) -6-CF_Three       H
CH_Three       H H H F (D-23-2b) -6-CF_Three       F
CH_Three       H H H F (D-23-2b) -6-OCH_Three       H
CH_Three       H H H F (D-23-2b) -6-OCH_Three       F
CH_Three       H H H F (D-23-2b) -6-CN H
CH_Three       H H H F (D-23-2b) -6-CN F
CH_Three       H H H Cl H H
CH_Three       H H H Cl Cl H
CH_Three       H H H Cl Br H
CH_Three       H H H Cl I H
CH_Three       H H H Cl CH_Three             H
CH_Three(S) H H H Cl CH_Three             H
CH_Three       H H H Cl CH_Three             F
CH_Three       H H H Cl CH_Three             Cl
CH_Three       H H H Cl Et H
CH_Three(S) H H H Cl Et H
CH_Three       H H H Cl Et F
CH_Three       H H H Cl Et Cl
CH_Three       H H H Cl n-Pr H
CH_Three(S) H H H Cl n-Pr H
CH_Three       H H H Cl n-Pr F
CH_Three       H H H Cl n-Pr Cl
CH_Three       H H H Cl i-Pr H
CH_Three(S) H H H Cl i-Pr H
CH_Three       H H H Cl i-Pr F
CH_Three       H H H Cl i-Pr Cl
CH_Three       H H H Cl c-Pr H
CH_Three(S) H H H Cl c-Pr H
CH_Three       H H H Cl c-Pr F
CH_Three       H H H Cl c-Pr Cl
CH_Three       H H H Cl T-2 H
CH_Three(S) H H H Cl T-2 H
CH_Three       H H H Cl T-2 F
CH_Three       H H H Cl T-2 Cl
CH_Three       H H H Cl c-Bu H
CH_Three(S) H H H Cl c-Bu H
CH_Three       H H H Cl c-Bu F
CH_Three       H H H Cl c-Bu Cl
CH_Three       H H H Cl t-Bu H
CH_Three(S) H H H Cl t-Bu H
CH_Three       H H H Cl t-Bu F
CH_Three       H H H Cl t-Bu Cl
CH_Three       H H H Cl T-1 H
CH_Three(S) H H H Cl T-1 H
CH_Three       H H H Cl T-1 F
CH_Three       H H H Cl T-1 Cl
CH_Three       H H H Cl T-3 H
CH_Three       H H H Cl c-Pen H
CH_Three       H H H Cl T-10 H
CH_Three       H H H Cl T-11 H
CH_Three       H H H Cl c-Hex H
CH_Three       H H H Cl CH_TwoF H
CH_Three(S) H H H Cl CH_TwoF H
CH_Three       H H H Cl CH_TwoF F
CH_Three       H H H Cl CH_TwoF Cl
CH_Three       H H H Cl CHF_Two             H
CH_Three       H H H Cl CF_Three             H
CH_Three       H H H Cl C (CH_Three)_TwoF H
CH_Three(S) H H H Cl C (CH_Three)_TwoF H
CH_Three       H H H Cl C (CH_Three)_TwoF F
CH_Three       H H H Cl C (CH_Three)_TwoF Cl
CH_Three       H H H Cl T-4 H
CH_Three(S) H H H Cl T-4 H
CH_Three       H H H Cl T-4 F
CH_Three       H H H Cl T-4 Cl
CH_Three       H H H Cl T-5 H
CH_Three(S) H H H Cl T-5 H
CH_Three       H H H Cl T-5 F
CH_Three       H H H Cl T-5 Cl
CH_Three       H H H Cl T-6 H
CH_Three(S) H H H Cl T-6 H
CH_Three       H H H Cl T-6 F
CH_Three       H H H Cl T-6 Cl
CH_Three       H H H Cl T-7 H
CH_Three(S) H H H Cl T-7 H
CH_Three       H H H Cl T-7 F
CH_Three       H H H Cl T-7 Cl
CH_Three       H H H Cl T-8 H
CH_Three       H H H Cl T-13 H
CH_Three(S) H H H Cl T-13 H
CH_Three       H H H Cl T-13 F
CH_Three       H H H Cl T-13 Cl
CH_Three       H H H Cl T-9 H
CH_Three       H H H Cl T-14 H
CH_Three       H H H Cl CH_TwoOCH_Three           H
CH_Three(S) H H H Cl CH_TwoOCH_Three           H
CH_Three       H H H Cl CH_TwoOCH_Three           F
CH_Three       H H H Cl CH_TwoOCH_Three           Cl
CH_Three       H H H Cl CH_TwoOEt H
CH_Three       H H H Cl CH_TwoOBu-t H
CH_Three       H H H Cl CH_TwoOCH_TwoCF_Three          H
CH_Three       H H H Cl CH_TwoOCH_TwoOCH_Three         H
CH_Three       H H H Cl C (CH_Three)_TwoOH H
CH_Three       H H H Cl C (CH_Three)_TwoOCH_Three         H
CH_Three(S) H H H Cl C (CH_Three)_TwoOCH_Three         H
CH_Three       H H H Cl C (CH_Three)_TwoOCH_Three         F
CH_Three       H H H Cl C (CH_Three)_TwoOCH_Three         Cl
CH_Three       H H H Cl C (CH_Three)_TwoOCH_TwoCF_Three        H
CH_Three       H H H Cl CH (OCH_Three)_Two          H
CH_Three       H H H Cl T-12 H
CH_Three       H H H Cl Si (CH_Three)_Three           H
CH_Three(S) H H H Cl Si (CH_Three)_Three           H
CH_Three       H H H Cl Si (CH_Three)_Three           F
CH_Three       H H H Cl Si (CH_Three)_Three           Cl
CH_Three       H H H Cl Si (CH_Three)_TwoBu-t H
CH_Three       H H H Cl Si (CH_Three)_TwoPh H
CH_Three       H H H Cl CH = NOCH_Three           H
CH_Three       H H H Cl C (CH_Three) = NOCH_Three         H
CH_Three       H H H Cl Ph H
CH_Three       H H H Cl Ph-2-F H
CH_Three(S) H H H Cl Ph-2-F H
CH_Three       H H H Cl Ph-2-F F
CH_Three       H H H Cl Ph-3-F H
CH_Three(S) H H H Cl Ph-3-F H
CH_Three       H H H Cl Ph-3-F F
CH_Three       H H H Cl Ph-4-F H
CH_Three(S) H H H Cl Ph-4-F H
CH_Three       H H H Cl Ph-4-F F
CH_Three       H H H Cl Ph-2-Cl H
CH_Three       H H H Cl Ph-3-Cl H
CH_Three(S) H H H Cl Ph-3-Cl H
CH_Three       H H H Cl Ph-3-Cl F
CH_Three       H H H Cl Ph-4-Cl H
CH_Three(S) H H H Cl Ph-4-Cl H
CH_Three       H H H Cl Ph-4-Cl F
CH_Three       H H H Cl Ph-4-Br H
CH_Three       H H H Cl Ph-2-CH_Three           H
CH_Three(S) H H H Cl Ph-2-CH_Three           H
CH_Three       H H H Cl Ph-2-CH_Three           F
CH_Three       H H H Cl Ph-3-CH_Three           H
CH_Three(S) H H H Cl Ph-3-CH_Three           H
CH_Three       H H H Cl Ph-3-CH_Three           F
CH_Three       H H H Cl Ph-4-CH_Three           H
CH_Three(S) H H H Cl Ph-4-CH_Three           H
CH_Three       H H H Cl Ph-4-CH_Three           F
CH_Three       H H H Cl Ph-4-Bu-t H
CH_Three       H H H Cl Ph-2-CF_Three           H
CH_Three(S) H H H Cl Ph-2-CF_Three           H
CH_Three       H H H Cl Ph-2-CF_Three           F
CH_Three       H H H Cl Ph-3-CF_Three           H
CH_Three(S) H H H Cl Ph-3-CF_Three           H
CH_Three       H H H Cl Ph-3-CF_Three           F
CH_Three       H H H Cl Ph-4-CF_Three           H
CH_Three(S) H H H Cl Ph-4-CF_Three           H
CH_Three       H H H Cl Ph-4-CF_Three           F
CH_Three       H H H Cl Ph-2-OCH_Three          H
CH_Three       H H H Cl Ph-3-OCH_Three          H
CH_Three(S) H H H Cl Ph-3-OCH_Three          H
CH_Three       H H H Cl Ph-3-OCH_Three          F
CH_Three       H H H Cl Ph-4-OCH_Three          H
CH_Three(S) H H H Cl Ph-4-OCH_Three          H
CH_Three       H H H Cl Ph-4-OCH_Three          F
CH_Three       H H H Cl Ph-3-OCHF_Two         H
CH_Three       H H H Cl Ph-4-OCHF_Two         H
CH_Three       H H H Cl Ph-2-OCF_Three          H
CH_Three       H H H Cl Ph-3-OCF_Three          H
CH_Three       H H H Cl Ph-4-OCF_Three          H
CH_Three(S) H H H Cl Ph-4-OCF_Three          H
CH_Three       H H H Cl Ph-4-OCF_Three          F
CH_Three       H H H Cl Ph-2-SCH_Three          H
CH_Three       H H H Cl Ph-3-SCH_Three          H
CH_Three       H H H Cl Ph-4-SCH_Three          H
CH_Three       H H H Cl Ph-2-S (O) CH_Three        H
CH_Three       H H H Cl Ph-3-S (O) CH_Three        H
CH_Three       H H H Cl Ph-4-S (O) CH_Three        H
CH_Three       H H H Cl Ph-2-SO_TwoCH_Three         H
CH_Three       H H H Cl Ph-3-SO_TwoCH_Three         H
CH_Three       H H H Cl Ph-4-SO_TwoCH_Three         H
CH_Three       H H H Cl Ph-3-SCHF_Two         H
CH_Three       H H H Cl Ph-3-SO_TwoCHF_Two        H
CH_Three       H H H Cl Ph-2-SCF_Three          H
CH_Three       H H H Cl Ph-4-SCF_Three          H
CH_Three       H H H Cl Ph-4-SO_TwoCF_Three         H
CH_Three       H H H Cl Ph-2-NO_Two           H
CH_Three       H H H Cl Ph-3-NO_Two           H
CH_Three       H H H Cl Ph-4-NO_Two           H
CH_Three       H H H Cl Ph-2-CN H
CH_Three       H H H Cl Ph-3-CN H
CH_Three       H H H Cl Ph-4-CN H
CH_Three(S) H H H Cl Ph-4-CN H
CH_Three       H H H Cl Ph-4-CN F
CH_Three       H H H Cl Ph-2,3-F_Two          H
CH_Three       H H H Cl Ph-2,4-F_Two          H
CH_Three(S) H H H Cl Ph-2,4-F_Two          H
CH_Three       H H H Cl Ph-2,4-F_Two          F
CH_Three       H H H Cl Ph-2,5-F_Two          H
CH_Three       H H H Cl Ph-2,6-F_Two          H
CH_Three       H H H Cl Ph-3,4-F_Two          H
CH_Three(S) H H H Cl Ph-3,4-F_Two          H
CH_Three       H H H Cl Ph-3,4-F_Two          F
CH_Three       H H H Cl Ph-3,5-F_Two          H
CH_Three       H H H Cl Ph-2-Cl-4-F H
CH_Three       H H H Cl Ph-2-F-3-Cl H
CH_Three       H H H Cl Ph-3-Cl-4-F H
CH_Three(S) H H H Cl Ph-3-Cl-4-F H
CH_Three       H H H Cl Ph-3-Cl-4-F F
CH_Three       H H H Cl Ph-2-F-4-Cl H
CH_Three(S) H H H Cl Ph-2-F-4-Cl H
CH_Three       H H H Cl Ph-2-F-4-Cl F
CH_Three       H H H Cl Ph-3-F-4-Cl H
CH_Three(S) H H H Cl Ph-3-F-4-Cl H
CH_Three       H H H Cl Ph-3-F-4-Cl F
CH_Three       H H H Cl Ph-3,4-Cl_Two          H
CH_Three(S) H H H Cl Ph-3,4-Cl_Two          H
CH_Three       H H H Cl Ph-3,4-Cl_Two          F
CH_Three       H H H Cl Ph-2-F-4-Br H
CH_Three       H H H Cl Ph-3-F-4-Br H
CH_Three       H H H Cl Ph-2-CH_Three-3-F H
CH_Three       H H H Cl Ph-2-CH_Three-4-F H
CH_Three       H H H Cl Ph-2-F-3-CH_Three         H
CH_Three       H H H Cl Ph-3-CH_Three-4-F H
CH_Three       H H H Cl Ph-2-F-4-CH_Three         H
CH_Three       H H H Cl Ph-3-F-4-CH_Three         H
CH_Three       H H H Cl Ph-2-CH_Three-4-Cl H
CH_Three       H H H Cl Ph-3-CH_Three-4-Cl H
CH_Three       H H H Cl Ph-2-CF_Three-3-F H
CH_Three       H H H Cl Ph-2-CF_Three-4-F H
CH_Three       H H H Cl Ph-2-F-3-CF_Three         H
CH_Three       H H H Cl Ph-3-CF_Three-4-F H
CH_Three       H H H Cl Ph-2-F-4-CF_Three         H
CH_Three       H H H Cl Ph-3-F-4-CF_Three         H
CH_Three       H H H Cl Ph-2-F-5-CF_Three         H
CH_Three       H H H Cl Ph-3-F-5-CF_Three         H
CH_Three       H H H Cl Ph-2-CF_Three-4-Cl H
CH_Three       H H H Cl Ph-3-CF_Three-4-Cl H
CH_Three       H H H Cl Ph-2-F-4-OCH_Three        H
CH_Three       H H H Cl Ph-3-F-4-OCH_Three        H
CH_Three       H H H Cl Ph-2-F-4-OCHF_Two        H
CH_Three       H H H Cl Ph-3-F-4-OCHF_Two        H
CH_Three       H H H Cl Ph-2-F-4-OCF_Three        H
CH_Three       H H H Cl Ph-3-F-4-OCF_Three        H
CH_Three(S) H H H Cl Ph-3-F-4-OCF_Three        H
CH_Three       H H H Cl Ph-3-F-4-OCF_Three        F
CH_Three       H H H Cl Ph-2-F-4-CN H
CH_Three       H H H Cl Ph-3-F-4-CN H
CH_Three       H H H Cl Ph-2,3,4-F_Three         H
CH_Three       H H H Cl Ph-2,3,5-F_Three         H
CH_Three       H H H Cl Ph-2,3,6-F_Three         H
CH_Three       H H H Cl Ph-2,4,5-F_Three         H
CH_Three       H H H Cl Ph-2,4,6-F_Three         H
CH_Three       H H H Cl Ph-3,4,5-F_Three         H
CH_Three       H H H Cl Ph-2,3-F_Two-4-Cl H
CH_Three       H H H Cl Ph-2,5-F_Two-4-Cl H
CH_Three       H H H Cl Ph-2,6-F_Two-4-Cl H
CH_Three       H H H Cl Ph-3,5-F_Two-4-Cl H
CH_Three       H H H Cl Ph-2-F-4-Cl-5-CH_Three      H
CH_Three       H H H Cl Ph-2,5-F_Two-4-CF_Three       H
CH_Three       H H H Cl Ph-2,3-F_Two-4-OCH_Three       H
CH_Three       H H H Cl Ph-2,5-F_Two-4-OCH_Three       H
CH_Three       H H H Cl Ph-2,6-F_Two-4-OCH_Three       H
CH_Three       H H H Cl Ph-3,5-F_Two-4-OCH_Three       H
CH_Three       H H H Cl D-1-1a H
CH_Three       H H H Cl (D-1-1b) -5-F H
CH_Three       H H H Cl (D-1-1b) -4-Br H
CH_Three       H H H Cl (D-1-1b) -5-Br H
CH_Three       H H H Cl (D-1-1b) -3-CH_Three        H
CH_Three       H H H Cl (D-1-1b) -4-CH_Three        H
CH_Three       H H H Cl (D-1-1b) -5-CH_Three        H
CH_Three       H H H Cl (D-1-1b) -5-CF_Three        H
CH_Three       H H H Cl (D-1-1b) -5-OCH_Three        H
CH_Three       H H H Cl (D-1-1b) -4-CN H
CH_Three       H H H Cl (D-1-1b) -5-CN H
CH_Three       H H H Cl D-1-2a H
CH_Three       H H H Cl (D-1-2b) -2-F H
CH_Three       H H H Cl (D-1-2b) -2-CH_Three        H
CH_Three       H H H Cl (D-1-2b) -4-CH_Three        H
CH_Three       H H H Cl (D-1-2b) -5-CH_Three        H
CH_Three       H H H Cl (D-1-2b) -5-OCH_Three        H
CH_Three       H H H Cl (D-1-2b) -5-CN H
CH_Three       H H H Cl (D-1-2b) -2,5- (CH_Three)_Two     H
CH_Three       H H H Cl D-2-1a H
CH_Three       H H H Cl (D-2-1b) -3-F H
CH_Three       H H H Cl (D-2-1b) -4-F H
CH_Three       H H H Cl (D-2-1b) -5-F H
CH_Three(S) H H H Cl (D-2-1b) -5-F H
CH_Three       H H H Cl (D-2-1b) -5-F F
CH_Three       H H H Cl (D-2-1b) -5-Cl H
CH_Three       H H H Cl (D-2-1b) -5-CH_Three        H
CH_Three       H H H Cl (D-2-1b) -5-OCH_Three       H
CH_Three       H H H Cl D-2-2a H
CH_Three       H H H Cl (D-2-2b) -2-F H
CH_Three       H H H Cl (D-2-2b) -4-F H
CH_Three       H H H Cl (D-2-2b) -5-F H
CH_Three       H H H Cl (D-2-2b) -5-Cl H
CH_Three       H H H Cl (D-2-2b) -5-CN H
CH_Three       H H H Cl (D-6-2a) -1-CH_Three        H
CH_Three       H H H Cl (D-6-2b) -1-CH_Three-3-CF_Three     H
CH_Three       H H H Cl (D-7-1b) -4-CH_Three        H
CH_Three       H H H Cl (D-7-1b) -4-CF_Three        H
CH_Three       H H H Cl D-8-1a H
CH_Three       H H H Cl (D-8-1b) -4-F H
CH_Three       H H H Cl (D-8-1b) -4-CH_Three        H
CH_Three       H H H Cl (D-8-1b) -5-CH_Three        H
CH_Three       H H H Cl (D-8-1b) -4-CF_Three        H
CH_Three       H H H Cl D-8-2a H
CH_Three       H H H Cl (D-8-2b) -2-CH_Three        H
CH_Three(S) H H H Cl (D-8-2b) -2-CH_Three        H
CH_Three       H H H Cl (D-8-2b) -2-CH_Three        F
CH_Three       H H H Cl (D-8-2b) -5-CH_Three        H
CH_Three       H H H Cl D-8-3a H
CH_Three       H H H Cl (D-8-3b) -2-CH_Three        H
CH_Three       H H H Cl D-23-1a H
CH_Three       H H H Cl (D-23-1b) -3-F H
CH_Three       H H H Cl (D-23-1b) -3-Cl H
CH_Three       H H H Cl (D-23-1b) -3-CH_Three       H
CH_Three       H H H Cl (D-23-1b) -4-Cl H
CH_Three       H H H Cl (D-23-1b) -4-CH_Three       H
CH_Three       H H H Cl (D-23-1b) -4-CF_Three       H
CH_Three       H H H Cl (D-23-1b) -5-F H
CH_Three       H H H Cl (D-23-1b) -5-CH_Three       H
CH_Three       H H H Cl (D-23-1b) -5-CF_Three       H
CH_Three       H H H Cl (D-23-1b) -5-OCF_Three       H
CH_Three       H H H Cl (D-23-1b) -5-CN H
CH_Three       H H H Cl (D-23-1b) -6-F H
CH_Three       H H H Cl (D-23-1b) -6-Cl H
CH_Three       H H H Cl (D-23-1b) -6-CH_Three       H
CH_Three       H H H Cl (D-23-1b) -6-CF_Three       H
CH_Three       H H H Cl (D-23-1b) -6-OCH_Three       H
CH_Three       H H H Cl (D-23-1b) -4,5-F_Two       H
CH_Three       H H H Cl (D-23-1b) -3-Cl-5-F H
CH_Three       H H H Cl (D-23-1b) -3,5-Cl_Two      H
CH_Three       H H H Cl (D-23-1b) -4,5-Cl_Two      H
CH_Three       H H H Cl (D-23-1b) -4-CH_Three-5-F H
CH_Three       H H H Cl (D-23-1b) -3-F-5-CH_Three     H
CH_Three       H H H Cl (D-23-1b) -5-F-6-CH_Three     H
CH_Three       H H H Cl (D-23-1b) -4-CH_Three-5-Cl H
CH_Three       H H H Cl (D-23-1b) -5-Cl-6-CH_Three     H
CH_Three       H H H Cl (D-23-1b) -4-CF_Three-5-F H
CH_Three       H H H Cl (D-23-1b) -3-F-5-CF_Three     H
CH_Three       H H H Cl (D-23-1b) -5-F-6-CF_Three     H
CH_Three       H H H Cl (D-23-1b) -3-CF_Three-5-Cl H
CH_Three       H H H Cl (D-23-1b) -4-CF_Three-5-Cl H
CH_Three       H H H Cl (D-23-1b) -5-Cl-6-CF_Three     H
CH_Three       H H H Cl (D-23-1b) -5-CF_Three-6-CH_Three    H
CH_Three       H H H Cl (D-23-1b) -4-OCH_Three-5-Cl H
CH_Three       H H H Cl (D-23-1b) -5-Cl-6-OCH_Three    H
CH_Three       H H H Cl (D-23-1b) -5-CF_Three-6-OCH_Three    H
CH_Three       H H H Cl (D-23-1b) -3-CH_Three-5-OCHF_Three   H
CH_Three       H H H Cl D-23-2a H
CH_Three       H H H Cl (D-23-2b) -2-F H
CH_Three       H H H Cl (D-23-2b) -2-Cl H
CH_Three       H H H Cl (D-23-2b) -2-CH_Three       H
CH_Three       H H H Cl (D-23-2b) -4-Cl H
CH_Three       H H H Cl (D-23-2b) -4-CH_Three       H
CH_Three       H H H Cl (D-23-2b) -5-F H
CH_Three       H H H Cl (D-23-2b) -5-Cl H
CH_Three       H H H Cl (D-23-2b) -5-CH_Three       H
CH_Three       H H H Cl (D-23-2b) -5-OCH_Three       H
CH_Three       H H H Cl (D-23-2b) -6-F H
CH_Three(S) H H H Cl (D-23-2b) -6-F H
CH_Three       H H H Cl (D-23-2b) -6-F F
CH_Three       H H H Cl (D-23-2b) -6-Cl H
CH_Three(S) H H H Cl (D-23-2b) -6-Cl H
CH_Three       H H H Cl (D-23-2b) -6-Cl F
CH_Three       H H H Cl (D-23-2b) -6-CH_Three       H
CH_Three       H H H Cl (D-23-2b) -6-CF_Three       H
CH_Three       H H H Cl (D-23-2b) -6-OCH_Three       H
CH_Three       H H H Cl (D-23-2b) -6-CN H
CH_Three       H H H Cl (D-23-2b) -4,6-F_Two       H
CH_Three       H H H Cl (D-23-2b) -4-F-6-Cl H
CH_Three       H H H Cl (D-23-2b) -5-F-6-CH_Three     H
CH_Three       H H H Cl (D-23-2b) -2-CH_Three-6-Cl H
CH_Three       H H H Cl (D-23-2b) -4-Cl-6-CH_Three     H
CH_Three       H H H Cl (D-23-2b) -5-Cl-6-CH_Three     H
CH_Three       H H H Cl (D-23-2b) -5-F-6-CF_Three     H
CH_Three       H H H Cl (D-23-2b) -4-Cl-6-CF_Three     H
CH_Three       H H H Cl (D-23-2b) -5-Cl-6-CF_Three     H
CH_Three      H H H Cl (D-23-2b) -2-CF_Three-6-CH_Three    H
CH_Three       H H H Cl (D-23-2b) -2-CH_Three-6-CF_Three    H
CH_Three       H H H Cl (D-23-2b) -4-CH_Three-6-CF_Three    H
CH_Three       H H H Cl (D-23-2b) -5-CH_Three-6-CF_Three    H
CH_Three       H H H Cl (D-23-2b) -4-F-6-OCH_Three     H
CH_Three       H H H Cl (D-23-2b) -5-F-6-OCH_Three     H
CH_Three       H H H Cl (D-23-2b) -5-OCH_Three-6-CF_Three    H
CH_Three       H H H Cl (D-23-2b) -2-CF_Three-6-OCH_Three    H
CH_Three       H H H Cl (D-23-2b) -5-CF_Three-6-OCH_Three    H
CH_Three       H H H Cl (D-23-2b) -2-CH_Three-6-OCHF_Two   H
CH_Three       H H H Cl (D-23-2b) -5-F-6-OCF_Three     H
CH_Three       H H H Cl D-23-3a H
CH_Three       H H H Cl (D-23-3b) -2-F H
CH_Three       H H H Cl (D-23-3b) -2-Cl H
CH_Three       H H H Cl (D-23-3b) -2-CH_Three       H
CH_Three       H H H Cl (D-23-3b) -2-CF_Three       H
CH_Three       H H H Cl (D-23-3b) -2-OCH_Three       H
CH_Three       H H H Cl (D-23-3b) -3-CH_Three       H
CH_Three       H H H Cl D-24-1a H
CH_Three       H H H Cl (D-24-1b) -6-CH_Three       H
CH_Three       H H H Cl (D-24-1b) -6-OCH_Three       H
CH_Three       H H H Cl (D-25-1b) -4-F H
CH_Three       H H H Cl (D-25-1b) -4-CF_Three       H
CH_Three       H H H Cl (D-25-1b) -4-OCH_Three       H
CH_Three       H H H Cl D-25-2a H
CH_Three       H H H Cl (D-25-2b) -2-Cl H
CH_Three       H H H Cl D-25-3a H
CH_Three       H H H Cl (D-25-3b) -2-Cl H
CH_Three       H H H Cl (D-25-3b) -2-CH_Three       H
CH_Three       H H H Cl (D-25-3b) -2-OCH_Three       H
CH_Three       H H H Cl D-26-1a H
CH_Three       H H H Cl (D-26-1b) -5-CH_Three       H
CH_Three       H H H Cl (D-26-1b) -6-Cl H
CH_Three       H H H CH_Three            CH_Three             H
CH_Three       H H H CH_Three           c-Pr H
CH_Three       H H H CH_Three           t-Bu H
CH_Three       H H H CH_Three         C (CH_Three)_TwoF H
CH_Three       H H H CH_Three         Si (CH_Three)_Three           H
CH_Three       H H H CH_Three          Ph-2-F H
CH_Three       H H H CH_Three          Ph-3-F H
CH_Three       H H H CH_Three          Ph-4-F H
CH_Three       H H H CH_Three       (D-2-1b) -5-F H
CH_Three       H H H CH_Three      (D-8-2b) -2-CH_Three        H
CH_Three       H H H CH_Three      (D-23-1b) -5-CF_Three       H
CH_Three       H H H CH_Three      (D-23-2b) -6-F H
CH_Three       H H H CH_Three      (D-23-2b) -6-Cl H
CH_Three       H H H CH_Three      (D-23-2b) -6-CF_Three       H
CH_Three       H F H F CH_Three             H
CH_Three       H F H F c-Pr H
CH_Three       H F H F t-Bu H
CH_Three       H F H F C (CH_Three)_TwoF H
CH_Three       H F H F Si (CH_Three)_Three           H
CH_Three       H F H F Ph-2-F H
CH_Three       H F H F Ph-3-F H
CH_Three       H F H F Ph-4-F H
CH_Three       H F H F (D-2-1b) -5-F H
CH_Three       H F H F (D-8-2b) -2-CH_Three        H
CH_Three       H F H F (D-23-1b) -5-CF_Three       H
CH_Three       H F H F (D-23-2b) -6-F H
CH_Three       H F H F (D-23-2b) -6-Cl H
CH_Three       H F H F (D-23-2b) -6-CF_Three       H
CH_Three       H F H Cl CH_Three             H
CH_Three       H F H Cl c-Pr H
CH_Three       H F H Cl t-Bu H
CH_Three      H F H Cl C (CH_Three)_TwoF H
CH_Three       H F H Cl Si (CH_Three)_Three           H
CH_Three       H F H Cl Ph-2-F H
CH_Three       H F H Cl Ph-3-F H
CH_Three       H F H Cl Ph-4-F H
CH_Three       H F H Cl (D-2-1b) -5-F H
CH_Three       H F H Cl (D-8-2b) -2-CH_Three        H
CH_Three       H F H Cl (D-23-1b) -5-CF_Three       H
CH_Three       H F H Cl (D-23-2b) -6-F H
CH_Three       H F H Cl (D-23-2b) -6-Cl H
CH_Three       H F H Cl (D-23-2b) -6-CF_Three       H
CH_Three       H F F Cl CH_Three             H
CH_Three       H F F Cl c-Pr H
CH_Three       H F F Cl t-Bu H
CH_Three       H F F Cl C (CH_Three)_TwoF H
CH_Three       H F F Cl Si (CH_Three)_Three           H
CH_Three       H F F Cl Ph-2-F H
CH_Three       H F F Cl Ph-3-F H
CH_Three       H F F Cl Ph-4-F H
CH_Three       H F F Cl T-15 H
CH_Three       H F F Cl T-16 H
CH_Three       H F F Cl T-17 H
CH_Three       H F F Cl T-18 H
CH_Three       H F F Cl T-19 H
CH_Three       H F F Cl T-20 H
CH_Three       H F F Cl T-21 H
CH_Three       H F F Cl T-22 H
CH_Three       H F F Cl T-23 H
CH_Three       H F F Cl T-24 H
CH_Three       H F F Cl T-25 H
CH_Three       H F F Cl T-26 H
CH_Three       H F F Cl T-27 H
CH_Three       H F F Cl T-28 H
CH_Three       H F F Cl T-29 H
CH_Three       H F F Cl T-30 H
CH_Three       H F F Cl T-31 H
CH_Three       H F F Cl T-32 H
CH_Three       H F F Cl T-33 H
CH_Three       H F F Cl T-34 H
CH_Three       H F F Cl T-35 H
CH_Three       H F F Cl T-36 H
CH_Three       H F F Cl T-37 H
CH_Three       H F F Cl T-38 H
CH_Three       H F F Cl T-39 H
CH_Three       H F F Cl T-40 H
CH_Three       H F F Cl T-41 H
CH_Three       H F F Cl T-42 H
CH_Three       H F F Cl T-43 H
CH_Three       H F F Cl T-44 H
CH_Three       H F F Cl T-45 H
CH_Three       H F F Cl T-46 H
CH_Three       H F F Cl T-47 H
CH_Three       H F F Cl T-48 H
CH_Three       H F F Cl T-49 H
CH_Three       H F F Cl T-50 H
CH_Three       H F F Cl T-51 H
CH_Three       H F F Cl T-52 H
CH_Three       H F F Cl T-53 H
CH_Three       H F F Cl T-54 H
CH_Three       H F F Cl T-55 H
CH_Three       H F F Cl T-56 H
CH_Three       H F F Cl T-57 H
CH_Three       H F F Cl T-58 H
CH_Three       H F F Cl T-59 H
CH_Three       H F F Cl T-60 H
CH_Three       H F F Cl T-61 H
CH_Three       H F F Cl T-62 H
CH_Three       H F F Cl T-63 H
CH_Three       H F F Cl T-64 H
CH_Three       H F F Cl T-65 H
CH_Three       H F F Cl T-66 H
CH_Three       H F F Cl T-67 H
CH_Three       H F F Cl T-68 H
CH_Three       H F F Cl T-69 H
CH_Three       H F F Cl T-70 H
CH_Three       H F F Cl T-71 H
CH_Three       H F F Cl T-72 H
CH_Three       H F F Cl T-73 H
CH_Three       H F F Cl T-74 H
CH_Three       H F F Cl T-75 H
CH_Three       H F F Cl T-76 H
CH_Three       H F F Cl T-77 H
CH_Three       H F F Cl T-78 H
CH_Three       H F F Cl T-79 H
CH_Three       H F F Cl D-1-1a H
CH_Three       H F F Cl (D-1-1b) -5-F H
CH_Three       H F F Cl (D-1-1b) -4-Br H
CH_Three       H F F Cl (D-1-1b) -5-Br H
CH_Three       H F F Cl (D-1-1b) -3-CH_Three        H
CH_Three       H F F Cl (D-1-1b) -4-CH_Three        H
CH_Three       H F F Cl (D-1-1b) -5-CH_Three        H
CH_Three       H F F Cl (D-1-1b) -5-CF_Three        H
CH_Three       H F F Cl D-1-1c H
CH_Three       H F F Cl D-1-2a H
CH_Three       H F F Cl (D-1-2b) -2-F H
CH_Three       H F F Cl (D-1-2b) -2-CH_Three        H
CH_Three       H F F Cl (D-1-2b) -4-CH_Three        H
CH_Three       H F F Cl (D-1-2b) -5-CH_Three        H
CH_Three       H F F Cl D-1-2c H
CH_Three       H F F Cl D-2-1a H
CH_Three       H F F Cl (D-2-1b) -3-F H
CH_Three       H F F Cl (D-2-1b) -4-F H
CH_Three       H F F Cl (D-2-1b) -5-F H
CH_Three(S) H F F Cl (D-2-1b) -5-F H
CH_Three       H F F Cl (D-2-1b) -4-Cl H
CH_Three       H F F Cl (D-2-1b) -5-Cl H
CH_Three       H F F Cl (D-2-1b) -4-CH_Three        H
CH_Three       H F F Cl (D-2-1b) -5-CH_Three        H
CH_Three       H F F Cl (D-2-1b) -4-OCH_Three       H
CH_Three       H F F Cl (D-2-1b) -5-OCH_Three       H
CH_Three       H F F Cl (D-2-1b) -4-CN H
CH_Three       H F F Cl (D-2-1b) -5-CN H
CH_Three       H F F Cl D-2-1c H
CH_Three       H F F Cl D-2-2a H
CH_Three       H F F Cl (D-2-2b) -2-F H
CH_Three       H F F Cl (D-2-2b) -4-F H
CH_Three       H F F Cl (D-2-2b) -5-F H
CH_Three       H F F Cl (D-2-2b) -5-Cl H
CH_Three       H F F Cl (D-2-2b) -5-CH_Three        H
CH_Three       H F F Cl (D-2-2b) -5-OCH_Three       H
CH_Three       H F F Cl (D-2-2b) -5-CN H
CH_Three       H F F Cl D-2-2c H
CH_Three       H F F Cl (D-6-1a) -1-CH_Three        H
CH_Three       H F F Cl (D-6-2a) -1-CH_Three        H
CH_Three       H F F Cl (D-6-2b) -1-CH_Three-3-CF_Three     H
CH_Three       H F F Cl (D-6-3a) -1-CH_Three        H
CH_Three       H F F Cl (D-7-1b) -4-CH_Three        H
CH_Three       H F F Cl (D-7-1b) -4-CF_Three        H
CH_Three      H F F Cl D-8-1a H
CH_Three       H F F Cl (D-8-1b) -4-F H
CH_Three       H F F Cl (D-8-1b) -4-CH_Three        H
CH_Three       H F F Cl (D-8-1b) -5-CH_Three        H
CH_Three       H F F Cl (D-8-1b) -4-CF_Three        H
CH_Three       H F F Cl D-8-2a H
CH_Three       H F F Cl (D-8-2b) -2-CH_Three        H
CH_Three(S) H F F Cl (D-8-2b) -2-CH_Three        H
CH_Three       H F F Cl (D-8-2b) -5-CH_Three        H
CH_Three       H F F Cl D-8-3a H
CH_Three       H F F Cl (D-8-3b) -2-CH_Three        H
CH_Three       H F F Cl D-23-1a H
CH_Three       H F F Cl (D-23-1b) -3-F H
CH_Three       H F F Cl (D-23-1b) -4-Cl H
CH_Three       H F F Cl (D-23-1b) -4-CH_Three       H
CH_Three       H F F Cl (D-23-1b) -4-CF_Three       H
CH_Three       H F F Cl (D-23-1b) -5-F H
CH_Three       H F F Cl (D-23-1b) -5-CH_Three       H
CH_Three       H F F Cl (D-23-1b) -5-CF_Three       H
CH_Three(S) H F F Cl (D-23-1b) -5-CF_Three       H
CH_Three       H F F Cl (D-23-1b) -5-OCF_Three       H
CH_Three       H F F Cl (D-23-1b) -5-CN H
CH_Three       H F F Cl (D-23-1b) -6-F H
CH_Three       H F F Cl (D-23-1b) -6-Cl H
CH_Three       H F F Cl (D-23-1b) -6-CH_Three       H
CH_Three       H F F Cl (D-23-1b) -6-CF_Three       H
CH_Three       H F F Cl (D-23-1b) -6-OCH_Three       H
CH_Three       H F F Cl (D-23-1b) -4,5-F_Two       H
CH_Three       H F F Cl (D-23-1b) -4,5-Cl_Two      H
CH_Three       H F F Cl (D-23-1b) -4-CH_Three-5-F H
CH_Three       H F F Cl (D-23-1b) -3-F-5-CH_Three     H
CH_Three       H F F Cl (D-23-1b) -5-F-6-CH_Three     H
CH_Three       H F F Cl (D-23-1b) -4-CH_Three-5-Cl H
CH_Three       H F F Cl (D-23-1b) -5-Cl-6-CH_Three     H
CH_Three       H F F Cl (D-23-1b) -4-CF_Three-5-F H
CH_Three       H F F Cl (D-23-1b) -3-F-5-CF_Three     H
CH_Three       H F F Cl (D-23-1b) -5-F-6-CF_Three     H
CH_Three       H F F Cl (D-23-1b) -3-CF_Three-5-Cl H
CH_Three       H F F Cl (D-23-1b) -4-CF_Three-5-Cl H
CH_Three       H F F Cl (D-23-1b) -5-Cl-6-CF_Three     H
CH_Three       H F F Cl (D-23-1b) -5-CF_Three-6-CH_Three    H
CH_Three       H F F Cl (D-23-1b) -4-OCH_Three-5-Cl H
CH_Three       H F F Cl (D-23-1b) -5-Cl-6-OCH_Three    H
CH_Three       H F F Cl (D-23-1b) -5-CF_Three-6-OCH_Three    H
CH_Three       H F F Cl D-23-1c H
CH_Three       H F F Cl D-23-1d H
CH_Three       H F F Cl D-23-2a H
CH_Three       H F F Cl (D-23-2b) -2-F H
CH_Three       H F F Cl (D-23-2b) -5-F H
CH_Three       H F F Cl (D-23-2b) -5-Cl H
CH_Three       H F F Cl (D-23-2b) -5-CH_Three       H
CH_Three       H F F Cl (D-23-2b) -5-OCH_Three       H
CH_Three       H F F Cl (D-23-2b) -6-F H
CH_Three(S) H F F Cl (D-23-2b) -6-F H
CH_Three       H F F Cl (D-23-2b) -6-Cl H
CH_Three(S) H F F Cl (D-23-2b) -6-Cl H
CH_Three       H F F Cl (D-23-2b) -6-CH_Three       H
CH_Three       H F F Cl (D-23-2b) -6-CF_Three       H
CH_Three(S) H F F Cl (D-23-2b) -6-CF_Three       H
CH_Three       H F F Cl (D-23-2b) -6-OCH_Three       H
CH_Three       H F F Cl (D-23-2b) -6-CN H
CH_Three       H F F Cl (D-23-2b) -4,6-F_Two       H
CH_Three       H F F Cl (D-23-2b) -4-F-6-Cl H
CH_Three       H F F Cl (D-23-2b) -5-F-6-CH_Three     H
CH_Three      H F F Cl (D-23-2b) -5-Cl-6-CH_Three     H
CH_Three       H F F Cl (D-23-2b) -5-F-6-CF_Three     H
CH_Three       H F F Cl (D-23-2b) -5-Cl-6-CF_Three     H
CH_Three       H F F Cl (D-23-2b) -5-CH_Three-6-CF_Three    H
CH_Three       H F F Cl (D-23-2b) -4-F-6-OCH_Three     H
CH_Three       H F F Cl (D-23-2b) -5-F-6-OCH_Three     H
CH_Three       H F F Cl (D-23-2b) -5-OCH_Three-6-CF_Three    H
CH_Three       H F F Cl (D-23-2b) -5-CF_Three-6-OCH_Three    H
CH_Three       H F F Cl (D-23-2b) -5-F-6-OCF_Three     H
CH_Three       H F F Cl D-23-2c H
CH_Three       H F F Cl D-23-2d H
CH_Three       H F F Cl D-23-2e H
CH_Three       H F F Cl D-23-2f H
CH_Three       H F F Cl D-23-2g H
CH_Three       H F F Cl D-23-3a H
CH_Three       H F F Cl (D-23-3b) -2-F H
CH_Three       H F F Cl (D-23-3b) -2-Cl H
CH_Three       H F F Cl (D-23-3b) -2-CH_Three       H
CH_Three       H F F Cl (D-23-3b) -2-CF_Three       H
CH_Three       H F F Cl (D-23-3b) -2-OCH_Three       H
CH_Three       H F F Cl (D-23-3b) -3-F H
CH_Three       H F F Cl D-24-1a H
CH_Three       H F F Cl (D-24-1b) -6-CH_Three       H
CH_Three       H F F Cl (D-24-1b) -6-OCH_Three       H
CH_Three       H F F Cl D-24-1c H
CH_Three       H F F Cl D-25-1a H
CH_Three       H F F Cl (D-25-1b) -4-F H
CH_Three       H F F Cl (D-25-1b) -4-CF_Three       H
CH_Three       H F F Cl (D-25-1b) -4-OCH_Three       H
CH_Three       H F F Cl D-25-1c H
CH_Three       H F F Cl D-25-2a H
CH_Three       H F F Cl (D-25-2b) -2-Cl H
CH_Three       H F F Cl D-25-3a H
CH_Three       H F F Cl (D-25-3b) -2-Cl H
CH_Three       H F F Cl (D-25-3b) -2-CH_Three       H
CH_Three       H F F Cl (D-25-3b) -2-OCH_Three       H
CH_Three       H F F Cl D-26-1a H
CH_Three       H F F Cl (D-26-1b) -5-CH_Three       H
CH_Three       H F F Cl (D-26-1b) -6-Cl H
CH_Three       H F F Cl D-26-1c H
CH_Three       H CH_Three        H Cl CH_Three             H
CH_Three       H CH_Three        H Cl c-Pr H
CH_Three       H CH_Three        H Cl t-Bu H
CH_Three       H CH_Three        H Cl C (CH_Three)_TwoF H
CH_Three       H CH_Three        H Cl Si (CH_Three)_Three           H
CH_Three       H CH_Three        H Cl Ph-2-F H
CH_Three       H CH_Three        H Cl Ph-3-F H
CH_Three       H CH_Three        H Cl Ph-4-F H
CH_Three       H CH_Three        H Cl (D-2-1b) -5-F H
CH_Three       H CH_Three        H Cl (D-8-2b) -2-CH_Three        H
CH_Three       H CH_Three        H Cl (D-23-1b) -5-CF_Three       H
CH_Three       H CH_Three        H Cl (D-23-2b) -6-F H
CH_Three       H CH_Three        H Cl (D-23-2b) -6-Cl H
CH_Three       H CH_Three        H Cl (D-23-2b) -6-CF_Three       H
CH_Three       H -CH_TwoCH_Two-Cl CH_Three             H
CH_Three       H -CH_TwoCH_Two-Cl c-Pr H
CH_Three       H -CH_TwoCH_Two-Cl t-Bu H
CH_Three       H -CH_TwoCH_Two-Cl C (CH_Three)_TwoF H
CH_Three       H -CH_TwoCH_Two-Cl Si (CH_Three)_Three           H
CH_Three       H -CH_TwoCH_Two-Cl Ph-2-F H
CH_Three       H -CH_TwoCH_Two-Cl Ph-3-F H
CH_Three       H -CH_TwoCH_Two-Cl Ph-4-F H
CH_Three       H -CH_TwoCH_Two-Cl (D-2-1b) -5-F H
CH_Three       H -CH_TwoCH_Two-Cl (D-8-2b) -2-CH_Three        H
CH_Three      H -CH_TwoCH_Two-Cl (D-23-2b) -6-F H
CH_Three       H -CH_TwoCH_Two-Cl (D-23-2b) -6-Cl H
CH_Three       H -CH_TwoCH_Two-Cl (D-23-1b) -5-CF_Three       H
CH_Three       H -CH_TwoCH_Two-Cl (D-23-2b) -6-CF_Three       H
CH_Three       H OCH_Three        H F CH_Three             H
CH_Three       H OCH_Three        H F CH_Three             F
CH_Three       H OCH_Three        H F c-Pr H
CH_Three       H OCH_Three        H F c-Pr F
CH_Three       H OCH_Three        H F t-Bu H
CH_Three       H OCH_Three        H F t-Bu F
CH_Three       H OCH_Three        H F C (CH_Three)_TwoF H
CH_Three       H OCH_Three        H F C (CH_Three)_TwoF F
CH_Three       H OCH_Three        H F Si (CH_Three)_Three           H
CH_Three       H OCH_Three        H F Si (CH_Three)_Three           F
CH_Three       H OCH_Three        H F Ph-2-F H
CH_Three       H OCH_Three        H F Ph-2-F F
CH_Three       H OCH_Three        H F Ph-3-F H
CH_Three       H OCH_Three        H F Ph-3-F F
CH_Three       H OCH_Three        H F Ph-4-F H
CH_Three       H OCH_Three        H F Ph-4-F F
CH_Three       H OCH_Three        H F (D-2-1b) -5-F H
CH_Three       H OCH_Three        H F (D-2-1b) -5-F F
CH_Three       H OCH_Three        H F (D-8-2b) -2-CH_Three        H
CH_Three       H OCH_Three        H F (D-8-2b) -2-CH_Three        F
CH_Three       H OCH_Three        H F (D-23-1b) -5-CF_Three       H
CH_Three       H OCH_Three        H F (D-23-1b) -5-CF_Three       F
CH_Three       H OCH_Three        H F (D-23-2b) -6-F H
CH_Three       H OCH_Three        H F (D-23-2b) -6-F F
CH_Three       H OCH_Three        H F (D-23-2b) -6-Cl H
CH_Three       H OCH_Three        H F (D-23-2b) -6-Cl F
CH_Three       H OCH_Three        H F (D-23-2b) -6-CF_Three       H
CH_Three       H OCH_Three        H F (D-23-2b) -6-CF_Three       F
CH_Three       H OCH_Three        H Cl CH_Three             H
CH_Three       H OCH_Three        H Cl Et H
CH_Three       H OCH_Three        H Cl n-Pr H
CH_Three       H OCH_Three        H Cl i-Pr H
CH_Three       H OCH_Three        H Cl c-Pr H
CH_Three       H OCH_Three        H Cl T-2 H
CH_Three       H OCH_Three        H Cl c-Bu H
CH_Three       H OCH_Three        H Cl t-Bu H
CH_Three       H OCH_Three        H Cl T-1 H
CH_Three       H OCH_Three        H Cl CH_TwoF H
CH_Three       H OCH_Three        H Cl C (CH_Three)_TwoF H
CH_Three       H OCH_Three        H Cl T-4 H
CH_Three       H OCH_Three        H Cl T-5 H
CH_Three       H OCH_Three        H Cl T-6 H
CH_Three       H OCH_Three        H Cl T-7 H
CH_Three       H OCH_Three        H Cl T-13 H
CH_Three       H OCH_Three        H Cl CH_TwoOCH_Three           H
CH_Three       H OCH_Three        H Cl C (CH_Three)_TwoOCH_Three         H
CH_Three       H OCH_Three        H Cl Si (CH_Three)_Three           H
CH_Three       H OCH_Three        H Cl Ph-2-F H
CH_Three       H OCH_Three        H Cl Ph-3-F H
CH_Three       H OCH_Three        H Cl Ph-4-F H
CH_Three       H OCH_Three        H Cl Ph-3-Cl H
CH_Three       H OCH_Three        H Cl Ph-4-Cl H
CH_Three       H OCH_Three        H Cl Ph-2-CH_Three           H
CH_Three       H OCH_Three        H Cl Ph-3-CH_Three           H
CH_Three       H OCH_Three        H Cl Ph-4-CH_Three           H
CH_Three       H OCH_Three        H Cl Ph-2-CF_Three           H
CH_Three       H OCH_Three        H Cl Ph-3-CF_Three           H
CH_Three       H OCH_Three        H Cl Ph-4-CF_Three           H
CH_Three       H OCH_Three        H Cl Ph-3-OCH_Three          H
CH_Three       H OCH_Three        H Cl Ph-4-OCH_Three          H
CH_Three       H OCH_Three        H Cl Ph-4-OCF_Three          H
CH_Three       H OCH_Three        H Cl Ph-4-CN H
CH_Three       H OCH_Three        H Cl Ph-2,4-F_Two          H
CH_Three       H OCH_Three        H Cl Ph-3,4-F_Two          H
CH_Three       H OCH_Three        H Cl Ph-3-Cl-4-F H
CH_Three       H OCH_Three        H Cl Ph-2-F-4-Cl H
CH_Three       H OCH_Three        H Cl Ph-3-F-4-Cl H
CH_Three       H OCH_Three        H Cl Ph-3,4-Cl_Two          H
CH_Three       H OCH_Three        H Cl Ph-3-F-4-OCF_Three        H
CH_Three       H OCH_Three        H Cl (D-2-1b) -5-F H
CH_Three(S) H OCH_Three(R) H Cl (D-2-1b) -5-F H
CH_Three(S) H OCH_Three(S) H Cl (D-2-1b) -5-F H
CH_Three       H OCH_Three        H Cl (D-2-1b) -5-Cl H
CH_Three       H OCH_Three        H Cl (D-2-1b) -5-CH_Three        H
CH_Three       H OCH_Three        H Cl (D-2-1b) -5-CF_Three        H
CH_Three       H OCH_Three        H Cl (D-2-1b) -5-OCH_Three       H
CH_Three       H OCH_Three        H Cl (D-2-2b) -5-Cl H
CH_Three       H OCH_Three        H Cl D-8-2a H
CH_Three       H OCH_Three        H Cl (D-8-2b) -2-CH_Three        H
CH_Three(S) H OCH_Three(R) H Cl (D-8-2b) -2-CH_Three        H
CH_Three(S) H OCH_Three(S) H Cl (D-8-2b) -2-CH_Three        H
CH_Three       H OCH_Three        H Cl (D-8-2b) -5-CH_Three        H
CH_Three       H OCH_Three        H Cl (D-23-1b) -5-CF_Three       H
CH_Three(S) H OCH_Three(R) H Cl (D-23-1b) -5-CF_Three       H
CH_Three(S) H OCH_Three(S) H Cl (D-23-1b) -5-CF_Three       H
CH_Three       H OCH_Three        H Cl (D-23-2b) -6-F H
CH_Three(S) H OCH_Three(R) H Cl (D-23-2b) -6-F H
CH_Three(S) H OCH_Three(S) H Cl (D-23-2b) -6-F H
CH_Three       H OCH_Three        H Cl (D-23-2b) -6-Cl H
CH_Three(S) H OCH_Three(R) H Cl (D-23-2b) -6-Cl H
CH_Three(S) H OCH_Three(S) H Cl (D-23-2b) -6-Cl H
CH_Three       H OCH_Three        H Cl (D-23-2b) -6-CH_Three       H
CH_Three       H OCH_Three        H Cl (D-23-2b) -6-CF_Three       H
CH_Three(S) H OCH_Three(R) H Cl (D-23-2b) -6-CF_Three       H
CH_Three(S) H OCH_Three(S) H Cl (D-23-2b) -6-CF_Three       H
CH_Three       H OCH_Three        H Cl (D-23-2b) -6-OCH_Three       H
CH_Three       H OCH_Three        H Cl (D-23-2b) -6-CN H
CH_Three       H OCH_Three        H CH_Three            CH_Three             H
CH_Three       H OCH_Three        H CH_Three           c-Pr H
CH_Three       H OCH_Three        H CH_Three           t-Bu H
CH_Three      H OCH_Three        H CH_Three         C (CH_Three)_TwoF H
CH_Three       H OCH_Three        H CH_Three         Si (CH_Three)_Three           H
CH_Three       H OCH_Three        H CH_Three          Ph-2-F H
CH_Three       H OCH_Three        H CH_Three          Ph-3-F H
CH_Three       H OCH_Three        H CH_Three          Ph-4-F H
CH_Three       H OCH_Three        H CH_Three       (D-2-1b) -5-F H
CH_Three       H OCH_Three        H CH_Three      (D-8-2b) -2-CH_Three        H
CH_Three       H OCH_Three        H CH_Three      (D-23-1b) -5-CF_Three       H
CH_Three       H OCH_Three        H CH_Three      (D-23-2b) -6-F H
CH_Three       H OCH_Three        H CH_Three      (D-23-2b) -6-Cl H
CH_Three       H OCH_Three        H CH_Three      (D-23-2b) -6-CF_Three       H
CH_Three       H OEt H F CH_Three             H
CH_Three       H OEt H F c-Pr H
CH_Three       H OEt H F t-Bu H
CH_Three       H OEt H F C (CH_Three)_TwoF H
CH_Three       H OEt H F Si (CH_Three)_Three           H
CH_Three       H OEt H F Ph-2-F H
CH_Three       H OEt H F Ph-3-F H
CH_Three       H OEt H F Ph-4-F H
CH_Three       H OEt H F (D-2-1b) -5-F H
CH_Three       H OEt H F (D-8-2b) -2-CH_Three        H
CH_Three       H OEt H F (D-23-1b) -5-CF_Three       H
CH_Three       H OEt H F (D-23-2b) -6-F H
CH_Three       H OEt H F (D-23-2b) -6-Cl H
CH_Three       H OEt H F (D-23-2b) -6-CF_Three       H
CH_Three       H OEt H Cl CH_Three             H
CH_Three       H OEt H Cl c-Pr H
CH_Three       H OEt H Cl t-Bu H
CH_Three       H OEt H Cl C (CH_Three)_TwoF H
CH_Three       H OEt H Cl Si (CH_Three)_Three           H
CH_Three       H OEt H Cl Ph-2-F H
CH_Three       H OEt H Cl Ph-3-F H
CH_Three       H OEt H Cl Ph-4-F H
CH_Three       H OEt H Cl (D-2-1b) -5-F H
CH_Three       H OEt H Cl (D-8-2b) -2-CH_Three        H
CH_Three       H OEt H Cl (D-23-1b) -5-CF_Three       H
CH_Three       H OEt H Cl (D-23-2b) -6-F H
CH_Three       H OEt H Cl (D-23-2b) -6-Cl H
CH_Three       H OEt H Cl (D-23-2b) -6-CF_Three       H
CH_Three       H OPr-n H Cl CH_Three             H
CH_Three       H OPr-n H Cl c-Pr H
CH_Three       H OPr-n H Cl t-Bu H
CH_Three       H OPr-n H Cl C (CH_Three)_TwoF H
CH_Three       H OPr-n H Cl Si (CH_Three)_Three          H
CH_Three       H OPr-n H Cl Ph-2-F H
CH_Three       H OPr-n H Cl Ph-3-F H
CH_Three       H OPr-n H Cl Ph-4-F H
CH_Three       H OPr-n H Cl (D-2-1b) -5-F H
CH_Three       H OPr-n H Cl (D-8-2b) -2-CH_Three        H
CH_Three       H OPr-n H Cl (D-23-1b) -5-CF_Three       H
CH_Three       H OPr-n H Cl (D-23-2b) -6-F H
CH_Three       H OPr-n H Cl (D-23-2b) -6-Cl H
CH_Three       H OPr-n H Cl (D-23-2b) -6-CF_Three       H
CH_Three       H OPr-i H Cl CH_Three             H
CH_Three       H OPr-i H Cl c-Pr H
CH_Three       H OPr-i H Cl t-Bu H
CH_Three       H OPr-i H Cl C (CH_Three)_TwoF H
CH_Three       H OPr-i H Cl Si (CH_Three)_Three           H
CH_Three       H OPr-i H Cl Ph-2-F H
CH_Three       H OPr-i H Cl Ph-3-F H
CH_Three       H OPr-i H Cl Ph-4-F H
CH_Three       H OPr-i H Cl (D-2-1b) -5-F H
CH_Three       H OPr-i H Cl (D-8-2b) -2-CH_Three        H
CH_Three       H OPr-i H Cl (D-23-1b) -5-CF_Three       H
CH_Three      H OPr-i H Cl (D-23-2b) -6-F H
CH_Three       H OPr-i H Cl (D-23-2b) -6-Cl H
CH_Three       H OPr-i H Cl (D-23-2b) -6-CF_Three       H
CH_Three       H OCH_TwoCF_Three      H Cl CH_Three             H
CH_Three       H OCH_TwoCF_Three      H Cl c-Pr H
CH_Three       H OCH_TwoCF_Three      H Cl t-Bu H
CH_Three       H OCH_TwoCF_Three      H Cl C (CH_Three)_TwoF H
CH_Three       H OCH_TwoCF_Three      H Cl Si (CH_Three)_Three           H
CH_Three       H OCH_TwoCF_Three      H Cl Ph-2-F H
CH_Three       H OCH_TwoCF_Three      H Cl Ph-3-F H
CH_Three       H OCH_TwoCF_Three      H Cl Ph-4-F H
CH_Three       H OCH_TwoCF_Three      H Cl (D-2-1b) -5-F H
CH_Three       H OCH_TwoCF_Three      H Cl (D-8-2b) -2-CH_Three        H
CH_Three       H OCH_TwoCF_Three      H Cl (D-23-1b) -5-CF_Three       H
CH_Three       H OCH_TwoCF_Three      H Cl (D-23-2b) -6-F H
CH_Three       H OCH_TwoCF_Three      H Cl (D-23-2b) -6-Cl H
CH_Three       H OCH_TwoCF_Three      H Cl (D-23-2b) -6-CF_Three       H
CH_Three       H OCH_TwoCN H Cl CH_Three             H
CH_Three       H OCH_TwoCN H Cl c-Pr H
CH_Three       H OCH_TwoCN H Cl t-Bu H
CH_Three       H OCH_TwoCN H Cl C (CH_Three)_TwoF H
CH_Three       H OCH_TwoCN H Cl Si (CH_Three)_Three           H
CH_Three       H OCH_TwoCN H Cl Ph-2-F H
CH_Three       H OCH_TwoCN H Cl Ph-3-F H
CH_Three       H OCH_TwoCN H Cl Ph-4-F H
CH_Three       H OCH_TwoCN H Cl (D-2-1b) -5-F H
CH_Three       H OCH_TwoCN H Cl (D-8-2b) -2-CH_Three        H
CH_Three       H OCH_TwoCN H Cl (D-23-1b) -5-CF_Three       H
CH_Three       H OCH_TwoCN H Cl (D-23-2b) -6-F H
CH_Three       H OCH_TwoCN H Cl (D-23-2b) -6-Cl H
CH_Three       H OCH_TwoCN H Cl (D-23-2b) -6-CF_Three       H
CH_Three       H OCH_TwoCH = CH_Two     H Cl CH_Three             H
CH_Three       H OCH_TwoCH = CH_Two     H Cl c-Pr H
CH_Three       H OCH_TwoCH = CH_Two     H Cl t-Bu H
CH_Three       H OCH_TwoCH = CH_Two     H Cl C (CH_Three)_TwoF H
CH_Three       H OCH_TwoCH = CH_Two     H Cl Si (CH_Three)_Three           H
CH_Three       H OCH_TwoCH = CH_Two     H Cl Ph-2-F H
CH_Three       H OCH_TwoCH = CH_Two     H Cl Ph-3-F H
CH_Three       H OCH_TwoCH = CH_Two     H Cl Ph-4-F H
CH_Three       H OCH_TwoCH = CH_Two     H Cl (D-2-1b) -5-F H
CH_Three       H OCH_TwoCH = CH_Two     H Cl (D-8-2b) -2-CH_Three        H
CH_Three       H OCH_TwoCH = CH_Two     H Cl (D-23-1b) -5-CF_Three       H
CH_Three       H OCH_TwoCH = CH_Two     H Cl (D-23-2b) -6-F H
CH_Three       H OCH_TwoCH = CH_Two     H Cl (D-23-2b) -6-Cl H
CH_Three       H OCH_TwoCH = CH_Two     H Cl (D-23-2b) -6-CF_Three       H
CH_Three       H OCH_TwoC≡CH H Cl CH_Three             H
CH_Three       H OCH_TwoC≡CH H Cl c-Pr H
CH_Three       H OCH_TwoC≡CH H Cl t-Bu H
CH_Three       H OCH_TwoC≡CH H Cl C (CH_Three)_TwoF H
CH_Three       H OCH_TwoC≡CH H Cl Si (CH_Three)_Three           H
CH_Three       H OCH_TwoC≡CH H Cl Ph-2-F H
CH_Three       H OCH_TwoC≡CH H Cl Ph-3-F H
CH_Three       H OCH_TwoC≡CH H Cl Ph-4-F H
CH_Three       H OCH_TwoC≡CH H Cl (D-2-1b) -5-F H
CH_Three       H OCH_TwoC≡CH H Cl (D-8-2b) -2-CH_Three        H
CH_Three       H OCH_TwoC≡CH H Cl (D-23-1b) -5-CF_Three       H
CH_Three       H OCH_TwoC≡CH H Cl (D-23-2b) -6-F H
CH_Three       H OCH_TwoC≡CH H Cl (D-23-2b) -6-Cl H
CH_Three       H OCH_TwoC≡CH H Cl (D-23-2b) -6-CF_Three       H
CH_Three       H OCH_TwoPh H Cl CH_Three             H
CH_Three       H OCH_TwoPh H Cl c-Pr H
CH_Three       H OCH_TwoPh H Cl t-Bu H
CH_Three       H OCH_TwoPh H Cl C (CH_Three)_TwoF H
CH_Three       H OCH_TwoPh H Cl Si (CH_Three)_Three           H
CH_Three       H OCH_TwoPh H Cl Ph-2-F H
CH_Three       H OCH_TwoPh H Cl Ph-3-F H
CH_Three       H OCH_TwoPh H Cl Ph-4-F H
CH_Three       H OCH_TwoPh H Cl (D-2-1b) -5-F H
CH_Three       H OCH_TwoPh H Cl (D-8-2b) -2-CH_Three        H
CH_Three       H OCH_TwoPh H Cl (D-23-1b) -5-CF_Three       H
CH_Three       H OCH_TwoPh H Cl (D-23-2b) -6-F H
CH_Three       H OCH_TwoPh H Cl (D-23-2b) -6-Cl H
CH_Three       H OCH_TwoPh H Cl (D-23-2b) -6-CF_Three       H
CH_Three       H SCH_Three        H Cl CH_Three             H
CH_Three       H SCH_Three        H Cl c-Pr H
CH_Three       H SCH_Three        H Cl t-Bu H
CH_Three       H SCH_Three        H Cl C (CH_Three)_TwoF H
CH_Three       H SCH_Three        H Cl Si (CH_Three)_Three           H
CH_Three       H SCH_Three        H Cl Ph-2-F H
CH_Three       H SCH_Three        H Cl Ph-3-F H
CH_Three       H SCH_Three        H Cl Ph-4-F H
CH_Three       H SCH_Three        H Cl (D-2-1b) -5-F H
CH_Three       H SCH_Three        H Cl (D-8-2b) -2-CH_Three        H
CH_Three       H SCH_Three        H Cl (D-23-1b) -5-CF_Three       H
CH_Three       H SCH_Three        H Cl (D-23-2b) -6-F H
CH_Three       H SCH_Three        H Cl (D-23-2b) -6-Cl H
CH_Three       H SCH_Three        H Cl (D-23-2b) -6-CF_Three       H
CH_Three       H NHOCH_Three       H Cl CH_Three            H
CH_Three       H NHOCH_Three       H Cl c-Pr H
CH_Three       H NHOCH_Three       H Cl t-Bu H
CH_Three       H NHOCH_Three       H Cl C (CH_Three)_TwoF H
CH_Three       H NHOCH_Three       H Cl Si (CH_Three)_Three           H
CH_Three       H NHOCH_Three       H Cl Ph-2-F H
CH_Three       H NHOCH_Three       H Cl Ph-3-F H
CH_Three       H NHOCH_Three       H Cl Ph-4-F H
CH_Three       H NHOCH_Three       H Cl (D-2-1b) -5-F H
CH_Three       H NHOCH_Three       H Cl (D-8-2b) -2-CH_Three        H
CH_Three       H NHOCH_Three       H Cl (D-23-1b) -5-CF_Three       H
CH_Three       H NHOCH_Three       H Cl (D-23-2b) -6-F H
CH_Three       H NHOCH_Three       H Cl (D-23-2b) -6-Cl H
CH_Three       H NHOCH_Three       H Cl (D-23-2b) -6-CF_Three       H
CH_Three       H NHOEt H Cl CH_Three             H
CH_Three       H NHOEt H Cl c-Pr H
CH_Three       H NHOEt H Cl t-Bu H
CH_Three       H NHOEt H Cl C (CH_Three)_TwoF H
CH_Three       H NHOEt H Cl Si (CH_Three)_Three           H
CH_Three       H NHOEt H Cl Ph-2-F H
CH_Three       H NHOEt H Cl Ph-3-F H
CH_Three       H NHOEt H Cl Ph-4-F H
CH_Three       H NHOEt H Cl (D-2-1b) -5-F H
CH_Three       H NHOEt H Cl (D-8-2b) -2-CH_Three        H
CH_Three       H NHOEt H Cl (D-23-1b) -5-CF_Three       H
CH_Three       H NHOEt H Cl (D-23-2b) -6-F H
CH_Three       H NHOEt H Cl (D-23-2b) -6-Cl H
CH_Three       H NHOEt H Cl (D-23-2b) -6-CF_Three       H
CH_Three       H NHOPr-i H Cl CH_Three             H
CH_Three       H NHOPr-i H Cl c-Pr H
CH_Three       H NHOPr-i H Cl t-Bu H
CH_Three       H NHOPr-i H Cl C (CH_Three)_TwoF H
CH_Three       H NHOPr-i H Cl Si (CH_Three)_Three           H
CH_Three       H NHOPr-i H Cl Ph-2-F H
CH_Three       H NHOPr-i H Cl Ph-3-F H
CH_Three       H NHOPr-i H Cl Ph-4-F H
CH_Three       H NHOPr-i H Cl (D-2-1b) -5-F H
CH_Three       H NHOPr-i H Cl (D-8-2b) -2-CH_Three        H
CH_Three       H NHOPr-i H Cl (D-23-1b) -5-CF_Three       H
CH_Three       H NHOPr-i H Cl (D-23-2b) -6-F H
CH_Three       H NHOPr-i H Cl (D-23-2b) -6-Cl H
CH_Three       H NHOPr-i H Cl (D-23-2b) -6-CF_Three       H
CH_Three       H NHOBu-s H Cl CH_Three             H
CH_Three       H NHOBu-s H Cl c-Pr H
CH_Three       H NHOBu-s H Cl t-Bu H
CH_Three       H NHOBu-s H Cl C (CH_Three)_TwoF H
CH_Three       H NHOBu-s H Cl Si (CH_Three)_Three           H
CH_Three       H NHOBu-s H Cl Ph-2-F H
CH_Three       H NHOBu-s H Cl Ph-3-F H
CH_Three       H NHOBu-s H Cl Ph-4-F H
CH_Three       H NHOBu-s H Cl (D-2-1b) -5-F H
CH_Three       H NHOBu-s H Cl (D-8-2b) -2-CH_Three        H
CH_Three       H NHOBu-s H Cl (D-23-1b) -5-CF_Three       H
CH_Three       H NHOBu-s H Cl (D-23-2b) -6-F H
CH_Three       H NHOBu-s H Cl (D-23-2b) -6-Cl H
CH_Three       H NHOBu-s H Cl (D-23-2b) -6-CF_Three       H
CH_Three       H NHOBu-t H Cl CH_Three             H
CH_Three       H NHOBu-t H Cl c-Pr H
CH_Three       H NHOBu-t H Cl t-Bu H
CH_Three       H NHOBu-t H Cl C (CH_Three)_TwoF H
CH_Three       H NHOBu-t H Cl Si (CH_Three)_Three           H
CH_Three       H NHOBu-t H Cl Ph-2-F H
CH_Three       H NHOBu-t H Cl Ph-3-F H
CH_Three       H NHOBu-t H Cl Ph-4-F H
CH_Three       H NHOBu-t H Cl (D-2-1b) -5-F H
CH_Three       H NHOBu-t H Cl (D-8-2b) -2-CH_Three        H
CH_Three       H NHOBu-t H Cl (D-23-1b) -5-CF_Three       H
CH_Three       H NHOBu-t H Cl (D-23-2b) -6-F H
CH_Three       H NHOBu-t H Cl (D-23-2b) -6-Cl H
CH_Three       H NHOBu-t H Cl (D-23-2b) -6-CF_Three       H
CH_Three       CH_Three        H H Cl CH_Three             H
CH_Three       CH_Three        H H Cl c-Pr H
CH_Three       CH_Three        H H Cl t-Bu H
CH_Three       CH_Three        H H Cl C (CH_Three)_TwoF H
CH_Three       CH_Three        H H Cl Si (CH_Three)_Three           H
CH_Three       CH_Three        H H Cl Ph-2-F H
CH_Three       CH_Three        H H Cl Ph-3-F H
CH_Three       CH_Three        H H Cl Ph-4-F H
CH_Three       CH_Three        H H Cl (D-2-1b) -5-F H
CH_Three       CH_Three        H H Cl (D-8-2b) -2-CH_Three        H
CH_Three       CH_Three        H H Cl (D-23-1b) -5-CF_Three       H
CH_Three       CH_Three        H H Cl (D-23-2b) -6-F H
CH_Three       CH_Three        H H Cl (D-23-2b) -6-Cl H
CH_Three       CH_Three        H H Cl (D-23-2b) -6-CF_Three       H
CH_Three       CH_Three        F F Cl CH_Three             H
CH_Three       CH_Three        F F Cl c-Pr H
CH_Three       CH_Three        F F Cl t-Bu H
CH_Three       CH_Three        F F Cl C (CH_Three)_TwoF H
CH_Three       CH_Three        F F Cl Si (CH_Three)_Three           H
CH_Three       CH_Three        F F Cl Ph-2-F H
CH_Three       CH_Three        F F Cl Ph-3-F H
CH_Three       CH_Three        F F Cl Ph-4-F H
CH_Three       CH_Three        F F Cl (D-2-1b) -5-F H
CH_Three       CH_Three        F F Cl (D-8-2b) -2-CH_Three        H
CH_Three       CH_Three        F F Cl (D-23-1b) -5-CF_Three       H
CH_Three       CH_Three        F F Cl (D-23-2b) -6-F H
CH_Three       CH_Three        F F Cl (D-23-2b) -6-Cl H
CH_Three       CH_Three        F F Cl (D-23-2b) -6-CF_Three       H
Et H H H Cl CH_Three             H
Et H H H Cl c-Pr H
Et H H H Cl t-Bu H
Et H H H Cl C (CH_Three)_TwoF H
Et H H H Cl Si (CH_Three)_Three           H
Et H H H Cl Ph-2-F H
Et H H H Cl Ph-3-F H
Et H H H Cl Ph-4-F H
Et H H H Cl (D-2-1b) -5-F H
Et H H H Cl (D-8-2b) -2-CH_Three        H
Et H H H Cl (D-23-1b) -5-CF_Three       H
Et H H H Cl (D-23-2b) -6-F H
Et H H H Cl (D-23-2b) -6-Cl H
Et H H H Cl (D-23-2b) -6-CF_Three       H
Et H F F Cl CH_Three             H
Et H F F Cl c-Pr H
Et H F F Cl t-Bu H
Et H F F Cl C (CH_Three)_TwoF H
Et H F F Cl Si (CH_Three)_Three           H
Et H F F Cl Ph-2-F H
Et H F F Cl Ph-3-F H
Et H F F Cl Ph-4-F H
Et H F F Cl (D-2-1b) -5-F H
Et H F F Cl (D-8-2b) -2-CH_Three        H
Et H F F Cl (D-23-1b) -5-CF_Three       H
Et H F F Cl (D-23-2b) -6-F H
Et H F F Cl (D-23-2b) -6-Cl H
Et H F F Cl (D-23-2b) -6-CF_Three       H
Et H OCH_Three        H Cl CH_Three             H
Et H OCH_Three        H Cl c-Pr H
Et H OCH_Three        H Cl t-Bu H
Et H OCH_Three        H Cl C (CH_Three)_TwoF H
Et H OCH_Three        H Cl Si (CH_Three)_Three           H
Et H OCH_Three        H Cl Ph-2-F H
Et H OCH_Three        H Cl Ph-3-F H
Et H OCH_Three        H Cl Ph-4-F H
Et H OCH_Three        H Cl (D-2-1b) -5-F H
Et H OCH_Three        H Cl (D-8-2b) -2-CH_Three       H
Et H OCH_Three        H Cl (D-23-1b) -5-CF_Three       H
Et H OCH_Three        H Cl (D-23-2b) -6-F H
Et H OCH_Three        H Cl (D-23-2b) -6-Cl H
Et H OCH_Three        H Cl (D-23-2b) -6-CF_Three       H
n-Pr H H H Cl CH_Three             H
n-Pr H H H Cl c-Pr H
n-Pr H H H Cl t-Bu H
n-Pr H H H Cl C (CH_Three)_TwoF H
n-Pr H H H Cl Si (CH_Three)_Three           H
n-Pr H H H Cl Ph-2-F H
n-Pr H H H Cl Ph-3-F H
n-Pr H H H Cl Ph-4-F H
n-Pr H H H Cl (D-2-1b) -5-F H
n-Pr H H H Cl (D-8-2b) -2-CH_Three        H
n-Pr H H H Cl (D-23-1b) -5-CF_Three       H
n-Pr H H H Cl (D-23-2b) -6-F H
n-Pr H H H Cl (D-23-2b) -6-Cl H
n-Pr H H H Cl (D-23-2b) -6-CF_Three       H
i-Pr H H H Cl CH_Three             H
i-Pr H H H Cl c-Pr H
i-Pr H H H Cl t-Bu H
i-Pr H H H Cl C (CH_Three)_TwoF H
i-Pr H H H Cl Si (CH_Three)_Three           H
i-Pr H H H Cl Ph-2-F H
i-Pr H H H Cl Ph-3-F H
i-Pr H H H Cl Ph-4-F H
i-Pr H H H Cl (D-2-1b) -5-F H
i-Pr H H H Cl (D-8-2b) -2-CH_Three        H
i-Pr H H H Cl (D-23-1b) -5-CF_Three       H
i-Pr H H H Cl (D-23-2b) -6-F H
i-Pr H H H Cl (D-23-2b) -6-Cl H
i-Pr H H H Cl (D-23-2b) -6-CF_Three       H
 -CH_TwoCH_Two-H H Cl CH_Three             H
 -CH_TwoCH_Two-H H Cl c-Pr H
 -CH_TwoCH_Two-H H Cl t-Bu H
 -CH_TwoCH_Two-H H Cl C (CH_Three)_TwoF H
 -CH_TwoCH_Two-H H Cl Si (CH_Three)_Three           H
 -CH_TwoCH_Two-H H Cl Ph-2-F H
 -CH_TwoCH_Two-H H Cl Ph-3-F H
 -CH_TwoCH_Two-H H Cl Ph-4-F H
 -CH_TwoCH_Two-H H Cl (D-2-1b) -5-F H
 -CH_TwoCH_Two-H H Cl (D-8-2b) -2-CH_Three        H
 -CH_TwoCH_Two-H H Cl (D-23-1b) -5-CF_Three       H
 -CH_TwoCH_Two-H H Cl (D-23-2b) -6-F H
 -CH_TwoCH_Two-H H Cl (D-23-2b) -6-Cl H
 -CH_TwoCH_Two-H H Cl (D-23-2b) -6-CF_Three       H
CH_TwoF H H H Cl CH_Three             H
CH_TwoF H H H Cl c-Pr H
CH_TwoF H H H Cl t-Bu H
CH_TwoF H H H Cl C (CH_Three)_TwoF H
CH_TwoF H H H Cl Si (CH_Three)_Three           H
CH_TwoF H H H Cl Ph-2-F H
CH_TwoF H H H Cl Ph-3-F H
CH_TwoF H H H Cl Ph-4-F H
CH_TwoF H H H Cl (D-2-1b) -5-F H
CH_TwoF H H H Cl (D-8-2b) -2-CH_Three        H
CH_TwoF H H H Cl (D-23-1b) -5-CF_Three       H
CH_TwoF H H H Cl (D-23-2b) -6-F H
CH_TwoF H H H Cl (D-23-2b) -6-Cl H
CH_TwoF H H H Cl (D-23-2b) -6-CF_Three       H
――――――――――――――――――――――――――――――――――――――――
  The compounds of the present invention include plant diseases and mammals (Mammalia) which occur in vascular plants (Tracheophyta) such as Pinaceae (Pinales), magnolias (magnoliids), monocots (monocots), and true dicotyledons (eudicots). Pathogens of vertebrate (Vertebrata) infections such as birds (Aves), reptiles (Reptilia) and teleosts (Actinopterygii), as well as plant- or animal-parasitic nematodes, hookheads, flatfishes and protozoa Pests can be controlled.

  Examples of plant pests include Ascomycota fungi, Basidiomycota fungi, Chitridiomycota fungi, Blastocladiomycota fungi, Mucomycotina fungi, and Kerzozoa. Cercozoa) Protists, Heterokontophyta Oomycetes, Actinobacteria Gram-positive fungi, Tenericutes Gram-positive fungi, Proteobacteria Gram-negative fungi and foliage Examples include the worms of Aphelenchida and the nematodes of Tylenchida. Among them, the compounds of the present invention are phytopathogenic fungi and leaf nematodes belonging to the phylum Ascomycota and Basidiomycota in particular. It exhibits an excellent control effect at low concentrations on plant parasitic nematodes belonging to the order Nematodes.

  Animal pests include Ascomycota fungi, Basidiomycota fungi, Actinobacteria gram-positive fungi, Filmicutes gram-positive fungi, Tenericutes gram-positive fungi , Phylum Proteobacteria (Proteobacteria) Gram-negative fungi and Enoplida, Rhabditida, Rhobditida, Strongylida, Ascaridida, Auricularia Spirurida nematodes, Coleoptera, Pseudophyllidea tapeworm, Cyclophyllidea tapeworm, Streptidida fluke, Echinostomida fluke Paramecium (Plagiorchiida), Posttestoria (Opisthorchiida), Amoebida, Piroplasmida sporozoa, Haemosporida sporozoa, Eucoccidiorida sporozoa Vestibuliferida ciliates, Trichomonadida flagellates, Diplomonadida flagellates, kinetoplasts (Kinetoplastida) flagellates, and the like. Among them, Capuchinidae (Cebidae), Cercopithecidae (Cercopithecidae), Hominidae (Hominidae), Rabbits (Leporidae), Chinchillidae (Chinchillidae), Guinea pigs (Caviidae), Rupidae (Cricetidae), and Rats (Murida) ), Squirrel family (Sciuridae), camelid family (Camelidae), wild boar family (Suidae), deer family (Cervidae), bovine family (Bovidae), feline family (Felidae), canine family (Canidae), weasel family (Mustelidae), Endoparasites of mammals (Mammalia) belonging to the equidae family (Equidae), kangaroo family (Macropodidae), etc. 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 nematocides, and the compounds of the present invention are also useful in mammals, fish, crustaceans, natural enemies It has a very useful feature that has almost no adverse effect on non-target organisms such as insects and useful insects.

  In using the compound of the present invention, it is usually mixed with a suitable solid carrier or liquid carrier, and further, if desired, a surfactant, a penetrant, a spreading agent, a thickener, a deicing agent, a binder, and an anti-caking agent. , Disintegrants, defoamers, preservatives, anti-decomposition agents, etc. to add soluble concentrates, emulsions (emulsifiable concentrates), wettable powders, water soluble powders, and granular water. Water dispersible granule, water soluble granule, suspension concentrate, concentrated emulsion, suspoemulsion, microemulsion, dustable powder ), Granules, tablets (tablets), emulsifiable gels, and the like. In addition, from the viewpoint of labor saving and improvement of safety, the preparation of any of the above dosage forms can be provided in a water-soluble package such as a water-soluble capsule or a bag of a water-soluble film.

  Solid carriers include, for example, quartz, calcite, sepiolite, dolomite, chalk, kaolinite, pyrophyllite, sericite, halothite, metahalothite, kibushi clay, frogme clay, pottery stone, siegrite, allophane , Shirasu, Kira, talc, bentonite, activated clay, acid clay, pumice, attapulgite, zeolite and diatomaceous earth; natural minerals such as calcined clay, perlite, shirasu balloon, vermiculite, attapulgase clay and calcined diatomaceous earth Baked goods, for example, inorganic salts such as magnesium carbonate, calcium carbonate, sodium carbonate, sodium hydrogen carbonate, ammonium sulfate, sodium sulfate, magnesium sulfate, diammonium hydrogen phosphate, ammonium dihydrogen phosphate and potassium chloride, for example, glucose, fructose , Then Sugars such as sugar and lactose, for example starch, powdered cellulose and polysaccharides such as dextrin, for example, organic substances such as urea, urea derivatives, benzoic acid and salts of benzoic acid, for example, wood flour, cork flour, corn cob, walnut shell and Examples include plants such as tobacco stems, fly ash, white carbon (for example, hydrous synthetic silica, anhydrous synthetic silica, and hydrous synthetic silicate), and fertilizers.

Liquid carriers include, for example, aromatic hydrocarbons such as xylene, alkyl (C ₉ or C ₁₀ etc.) benzene, phenyl xylyl ethane and alkyl (C ₁ or C ₃ etc.) 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, Pyrene glycol monoethyl ether, propylene glycol monopropyl ether, ethers such as propylene glycol monobutyl ether and propylene glycol monophenyl ether, ketones such as acetophenone, cyclohexanone and γ-butyrolactone, fatty acid methyl esters, dialkyl succinate, dialkyl glutamate, esters such as adipic acid dialkyl ester and dialkyl phthalate esters, N- alkyl (C _1, C ₈ or C _12, etc.) acid amide pyrrolidone, soybean oil, linseed oil, rapeseed oil, coconut oil, cottonseed oil and castor oil, etc. Oils, 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 sulfates, alkylbenzene sulfonates, lignin sulfonates, Killsulfosuccinate, naphthalene sulfonate, alkyl naphthalene sulfonate, salt of formalin condensate of naphthalene sulfonic acid, salt of formalin condensate of alkyl naphthalene sulfonic acid, polyoxyethylene alkyl ether sulfate or phosphate ester salt, polyoxy Ethylene (mono or di) alkyl phenyl ether sulfate or phosphate ester salts, polyoxyethylene (mono, di or tri) styryl phenyl ether sulfate or phosphate ester salts, polycarboxylates such as polyacrylates, polymaleates and Anionic surfactants such as a copolymer of maleic acid and an olefin) and polystyrene sulfonates; cationic surfactants such as alkylamine salts and alkylquaternary ammonium salts; Amphoteric surfactants such as mold, and silicone-based surfactants and fluorinated surfactants.

  The content of these surfactants is not particularly limited, but is preferably in the range of usually 0.05 to 40 parts by weight based on 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 amount of the applied compound of the present invention varies depending on the application scene, application time, application method, cultivated crops, and the like. Generally, the effective amount of the active ingredient is about 0.005 to 50 kg per hectare (ha).

  On the other hand, when the compound of the present invention is used for controlling endoparasites of mammals and birds as livestock, poultry and pets, an effective amount of the compound of the present invention is orally administered together with a pharmaceutical additive, and injected (intramuscularly, Parenteral administration such as subcutaneous, intravenous, intraperitoneal); transdermal administration such as dipping, 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 as molded articles using strips, plates, bands, collars, ear marks, limb bands, marking devices and the like. Upon administration, the compound of the present invention can be made into any dosage form suitable for the administration route.

  Any dosage forms that may be prepared include solid preparations, such as powders, granules, wettable powders, pellets, tablets, pills, capsules, molded products containing the active compound; solutions for injection, solutions for oral use, skin. Liquid preparations for use on or in the body cavity; solution preparations such as drop-on (Pour-on) preparations, spot-on preparations, flowable preparations and emulsions; semisolid preparations such as ointments and gels.

  The solid preparation can be used mainly for oral administration, or for transdermal administration after dilution with water or the like, or for environmental treatment. Solid preparations can be prepared by mixing the active compound with appropriate excipients, if necessary with the aid of excipients, and converting into the desired form. Suitable excipients include, for example, inorganic substances such as carbonates, bicarbonates, phosphates, aluminum oxides, silicas, clays and the like, and organic substances such as sugars, cellulose, ground grains, starches and the like.

  Injectable solutions can be administered intravenously, intramuscularly and subcutaneously. Injectable solutions dissolve the active compound in a suitable solvent and, if necessary, solubilisers, acids, bases, buffer salts, antioxidants. And an additive such as a protective agent. 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 the solubilizer include polyvinylpyrrolidone, polyoxyethylated castor oil, and polyoxyethylated sorbitan ester. Protecting agents include benzyl alcohol, trichlorobutanol, p-hydroxybenzoate and n-butanol.

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

  Flowables, emulsions, and the like 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 (immersion, bathing or washing). These solutions can be prepared in the same manner as the solutions for injection.

  Drop-on (Pour-on) and Drop-on (Spot-on) agents can be dripped or sprayed onto a limited area of the skin, whereby the active compound can be immersed in the skin and act systemically . Drops and drops may be prepared by dissolving, suspending or emulsifying the active component in a suitable skin-compatible solvent or solvent mixture. If necessary, auxiliary agents such as surfactants, colorants, absorption enhancers, 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 oils, DMF, liquid paraffin, light liquid paraffin, silicone, dimethylacetamide, N-methylpyrrolidone or 2,2-dimethyl-4-oxy-methylene-1, 3-dioxolane. Absorption enhancers include DMSO, isopropyl myristate, dipropylene glycol pelargonate, silicone oils, aliphatic esters, triglycerides and fatty alcohols. Antioxidants include sulfites, metabisulfites, ascorbic acid, butylhydroxytoluene, butylhydroxyanisole and tocopherol.

  Emulsions can be administered orally, dermally or as injections. The emulsion is prepared by dissolving the active ingredient in a hydrophobic phase or a hydrophilic phase, and dissolving the active ingredient with a suitable emulsifier, if necessary, further including a coloring agent, an absorption-promoting substance, a protective agent, an antioxidant, a light-shielding agent, and a thickening substance. By homogenizing with other phase solvents together with the auxiliaries.

Examples of the hydrophobic phase (oil) include paraffin oil, silicone oil, sesame oil, almond oil, castor oil, synthetic triglyceride, ethyl stearate, di-n-butyryl adipate, hexyl laurate, dipropylene glycol pelargonate, and branched chains. 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 non-ionic interfaces such as polyoxyethylated castor oil, polyoxyethylated sorbitan monoolefin, sorbitan monostearate, glyceryl monostearate, polyoxyethyl stearate, and alkylphenol polyglycol ether. Surfactants; amphoteric surfactants such as disodium N-lauryl-β-iminodipropionate and lecithin; anions such as sodium lauryl sulfate, fatty alcohol sulfate, and monoethanolamine salts of mono / dialkyl polyglycol orthophosphates. Cationic surfactants; and cationic surfactants such as cetyltrimethylammonium chloride.

  Other adjuvants include carboxymethylcellulose, methylcellulose, polyacrylate, alginate, gelatin, gum arabic, polyvinylpyrrolidone, polyvinyl alcohol, methyl vinyl ether, copolymers of maleic anhydride, polyethylene glycol, wax, colloidal silica.

  Semi-solid preparations can be administered by spreading or spreading on the skin or by introducing them into body cavities. Gels can be prepared by adding to the solution prepared above for injectable solutions a thickener sufficient to produce a clear, ointment-like viscous substance.

  The formulation examples of the preparations using the compound of the present invention are shown below. However, the composition 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 to 80 parts Solid carrier 5 to 98.9 parts Surfactant 1 to 10 parts Others 0 to 5 parts Other examples include anti-caking agents and decomposition inhibitors.

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

(Suspension)
Compound of the present invention 0.1 to 70 parts Liquid carrier 15 to 98.89 parts Surfactant 1 to 12 parts Others 0.01 to 30 parts Others include, for example, an antifreezing agent and a thickener.

(Granular 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, a binder and a decomposition inhibitor.

(Solution)
Compound of the present invention 0.01 to 70 parts Liquid carrier 20 to 99.99 parts Others 0 to 10 parts Others include, for example, an antifreezing agent and a spreading agent.

(Granules)
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, a binder and a decomposition inhibitor.

(Powder)
Compound of the present invention 0.01 to 30 parts Solid carrier 65 to 99.99 parts Others 0 to 5 parts Others include, for example, a drift inhibitor and a decomposition inhibitor.

  Next, Formulation Examples containing the compound of the present invention as an active ingredient will be shown more specifically, but the present invention is not limited thereto.

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

[Formulation Example 1] Water dispersant Compound of the present invention No. 2-007 20 parts Pyrophyllite 74 parts Solpol 50394 4 parts (mixture of nonionic surfactant and anionic surfactant: Toho Chemical Industry Co., Ltd.) Product name)
Carplex # 80D 2 parts (Synthetic hydrated silica: trade name of Shionogi & Co., Ltd.)
The above is uniformly mixed and pulverized to obtain a wettable powder.

[Formulation Example 2] Emulsion Inventive compound No. 3-002 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 are uniformly mixed to form an emulsion.

[Formulation Example 3] Emulsion Inventive compound No. 3-015 4 parts DBE 36 parts (mixture of dimethyl adipate, dimethyl glutarate and dimethyl succinate: trade name, manufactured by INVISTA)
Diisobutyl adipate 30 parts N-methylpyrrolidone 10 parts Soprofol BSU 14 parts (Nonionic surfactant: trade name of Rhodia)
6 parts of Rhodacal 70BC (anionic surfactant: trade name of Rhodia)
The above are uniformly mixed to form an emulsion.

[Formulation Example 4] Emulsion Inventive compound No. 3-016 4 parts DBE 11 parts (mixture of dimethyl adipate, dimethyl glutarate and dimethyl succinate: trade name, manufactured by INVISTA)
Diisobutyl adipate 30 parts N-methylpyrrolidone 5 parts Soprofol BSU 14 parts (nonionic surfactant: trade name of Rhodia)
6 parts of Rhodacal 70BC (anionic surfactant: trade name of Rhodia)
Propylene glycol 10 parts Water 20 parts The above are uniformly mixed to form an emulsion.

[Formulation Example 5] Suspension Compound of the present invention No. 3-017 25 parts Agrisol S-710 10 parts (nonionic surfactant: trade name of Kao Corporation)
0.5 parts of Lunox 1000C (anionic surfactant: trade name of Toho Chemical Industry Co., Ltd.)
Xanthan gum 0.2 part Water 64.3 parts After uniformly mixing the above, wet pulverization is performed to obtain a suspending agent.

[Compounding Example 6] Water dispersible granule 75 parts of the compound of the present invention No. 4-001 5 parts of Hytenol NE-15 (anionic surfactant: trade name of Daiichi Kogyo Seiyaku Co., Ltd.)
Vanillex N 10 parts (anionic surfactant: Nippon Paper Industries Co., Ltd.)
Carplex # 80D 10 parts (Synthetic hydrated silica: Shionogi & Co., Ltd. brand name)
After uniformly mixing and pulverizing the above, a small amount of water is added, and the mixture is stirred and mixed, granulated by an extrusion granulator, and dried to obtain a wettable powder.

[Compounding Example 7] Granules Compound of the present invention No. 4-002 5 parts Bentonite 50 parts Talc 45 parts After uniformly mixing and pulverizing the above, a small amount of water was added, followed by stirring and mixing, and granulation was performed using an extrusion granulator. And dried to form granules.

[Compounding Example 8] Powder Compound of the present invention No. 3-013 3 parts Carplex # 80D 0.5 parts (synthetic hydrous silicic acid: trade name of Shionogi & Co., Ltd.)
95 parts kaolinite 1.5 parts diisopropyl phosphate 1.5 parts or more are uniformly mixed and pulverized to form a powder.

  For use, each of the above-mentioned preparations is diluted 1 to 20,000-fold with water and sprayed so that the active ingredient becomes 0.005 to 50 kg per hectare (ha).

[Formulation Example 9] wettable powder preparation Compound of the present invention No. 1-005 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 of the present invention No. 1-009 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] Liquid formulation for spray No. 2-010 2 parts Dimethyl sulfoxide 10 parts 2-propanol 35 parts Acetone 53 parts [Formulation Example 12] transdermal Liquid preparation for administration Compound of the present invention No. 3-02 5 parts Hexylene glycol 50 parts Isopropanol 45 parts [Formulation Example 13] Liquid preparation for transdermal administration Compound of the present invention No. 2-015 5 parts Propylene glycol monomethyl ether 50 parts Dipropylene glycol 45 parts [Formulation Example 14] Transdermal administration ( Solution for dropping) Compound of the present invention No. 1-008 2 parts Light liquid paraffin 98 parts [Formulation Example 15] Solution for transdermal administration (Drip) Compound of the present invention No. 2-014 2 parts Light liquid paraffin 58 parts Olive oil 30 parts ODO-H 9 parts Shin-Etsu Silicone 1 part When the compound of the present invention is used as a fungicide for agricultural and horticultural use and a nematode controlling agent, an effective amount of the compound of the present invention can be used alone as an active ingredient, When formulating or spraying with other types of fungicides, other types of nematicides, insecticides, acaricides, plant growth regulators, herbicides, synergists, fertilizers, soil conditioners, etc. It may be mixed application.

  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. It can also be administered as a mixture with an anthelmintic or the like at the time of preparation or administration.

  In particular, by mixing and applying with other kinds of fungicides, other kinds of nematocides, other kinds of antibacterial agents or other kinds of anthelmintic agents, etc., expansion of the control spectrum by the additive and synergistic action of the mixed medicines, It can be expected to improve the pest control effect, reduce the control cost by reducing the amount of applied medicine, and furthermore, the effect of maintaining the control effect for a longer period of time can be expected. In particular, application by mixing with other fungicides, nematocides, antibacterial agents, and anthelmintic agents having different mechanisms of action is an extremely effective control method from the viewpoint of preventing the pests from acquiring drug resistance. . At this time, a combination with a plurality of known fungicides, known nematocides, known insecticides, known acaricides, known antibacterial agents, or known anthelmintic agents can be simultaneously performed.

  The kind of fungicide, nematicide, insecticide, acaricide, anthelmintic or antibacterial used in combination with the compound of the present invention is described in, for example, The Pesticide Manual, 16th edition, 2012 and the like. The compounds described are exemplified. Specific examples of the common names are as follows, but are not necessarily limited thereto.

Fungicide:
A: nucleic acid biosynthesis inhibitor benalaxyl (benalaxyl), benalaxyl-M (benalaxyl-M), furalaxyl (furalaxyl), metalaxyl (metalaxyl), metalaxyl-M (metalaxyl-M), ofurace, ofurace, oxadixyl,
Bupirimate, etirimol (ethirimol),
Hymexazol,
B: mitotic and mitotic inhibitor benomyl, carbendazim, fuberidazole, fubenidazole, thiabendazole, thiophanate-methyl,
Dietofencarb,
Ethaboxam, zoxamide,
Pencuron (pencycuron),
Fluopicolide,
C: respiratory inhibitor diflumetorim,
Benodanil, benzovindiflupyr, bixafen, boscalid, carboxin, carboxin, fenfuram, fluopyram, flutolanil, flaxapyroxad ), Furametpyr, isofetamid, isopyrazam, isopyrazam, mepronil, oxycarboxin, oxycarboxin, penflufen, penflufen, penthiopyrad, pidiflumetofid, pydiflumetid py ), Sedaxane, thifluzamide,
Azoxystrobin (azoxystrobin), cumoxystrobin (coumoxystrobin), dimoxystrobin (dimoxystrobin), enestrobin (enestrobin), enoxastrobin (enoxastrobin), famoxadone (famoxadone), fenamidone (fenamidone), phenaminestrobin ( fenaminstrobin), flufenoxystrobin, fluoxastrobin, fluoxastrobin, kresoxim-methyl, mandestrobin, metominostrobin, orysastrobin, orycastrobin Robin (picoxystrobin), pyraclostrobin (pyraclostrobin), pyrametostrobin (pyrametostrobin), pyraoxystrobin (pyraoxystrobin), pyribencarb-methyl (pyribencarb-methyl), pyriminostrobin (pyriminostrobin), triclopirical (Triclopyricab), trifloxystrobin,
Amisulbrom, cyazofamid,
Dinocap (dinocap), fluazinam (fluazinam), meptyldinocap (meptyldinocap),
Fentin, tributyltin oxide,
Silthiofam,
Amethoctrazine (ametoctradin),
D: amino acid and protein biosynthesis inhibitor cyprodinil (cyprodinil), mepanipyrim (mepanipyrim), pyrimethanil (pyrimethanil),
Blasticidin-S,
Kasugamycin,
E: drugs acting on signal transduction system proquinazid (proquinazid), quinoxyfen (quinoxyfen),
Fenpiclonil, fludioxonil,
Clozolinate (chlozolinate), iprodione (iprodione), procymidone (procymidone), vinclozolin (vinclozolin),
F; lipid and cell membrane synthesis inhibitors edifenphos, iprobenfos, isoprothiolane, pyrazophos,
Biphenyl, chloroneb, dichloran, ditriran, etridiazole, quintozene, technazen, tecnazene, tolclofos-methyl,
Propamocarb hydrochloride,
Bacillus subtilis (Bacillus subtilis, Strain: D747, FZB24, GBO3, HAI0404, MBI600, QST713, Y1336, etc.),
G: sterol biosynthesis inhibitor azaconazole, azaconazole, bitertanol, bromuconazole, cyproconazole, cyproconazole, diphenoconazole, diconiconazole, diniconazole-M, diniconazole-M Epoxyconazole (epoxiconazole), etaconazole (etaconazole), fenarimol (fenarimol), fenbuconazole (fenbuconazole), fluquinconazole (fluquinconazole), flusilazole (flusilazole), flutriafol (flutriafol), hexaconazole (hexaconazole), Imazalil, imibenconazole, imiconconazole, ipconazole, metconazole, microbutanil (myclobutanil), nuarimol (nuarimol), oxpoconazole fumarate (oxpoc) onazole fumarate), pefurazoate, penconazole, prochloraz (prochloraz), propiconazole (propiconazole), prothioconazole (prothioconazole), pyrifenox (pyrifenox), pyrisoxazole (pyrisoxazole), simeconazole, Tebuconazole (tebuconazole), tetraconazole (tetraconazole), triadimefon (triadimefon), triadimenol (triadimenol), triflumizole (triflumizole), trifolin (triforine), triticonazole (triticonazole),
Aldimorph, aldemorph, dodemorph-acetate, fenpropidin, fenpropimorph, fenpropimorph, piperaline, spiroxamine, spiroxamine, tridemorph,
Fenhexamid, fenpyrazamine,
H: cell wall synthesis inhibitor validamycin,
Polyoxins, polyoxin-D (polyoxorim),
Benthiavalicarb-isopropyl (benthiavalicarb-isopropyl), dimethomorph (dimethomorph), flumorph (flumorph), iprovalicarb (iprovalicarb), mandipropamide (mandipropamid), pyrimorph (pyrimorph), varifenalate (valifenalate),
I: melanin synthesis inhibitor phthalide, pyroquilon, tricyclazole,
Carpropamid, diclosymet, fenoxanil,
Tolprocarb,
P; plant resistance inducer acibenzolar-S-methyl (acibenzolar-S-methyl),
Probenazole,
Isotianil, tiadinil,
Laminarin,
M: multipoint drug Bordeaux mixture, cheshunt mixture, copper carbonate, basic, copper hydroxide, copper naphthenate , Copper oleate, copper oxychloride, copper sulfate, copper sulfate, basic, oxyquinoline copper (oxine copper), lime sulfur mixture (calcium) polysulfide), sulfur (sulfur), ambam (amobam), furbam (ferbam), mancozeb (mancozeb), maneb (maneb), metiram (metiram), polycarbamate (polycarbamate), propineb (propineb), thiuram (thiram), ziram (Ziram), captan, folpet, chlorothalonil, dichlofluanid, trilf Enid (tolylfluanid), guazatine (guazatine), iminoctadine - Arubeshiru salt (iminoctadine-albesilate), iminoctadine acetate (iminoctadine-triacetate), Anirajin (anilazine), dithianon (dithianon), Kinomechioneto (chinomethionat), Furuoruimido (fluoroimide),
And UN; unknown mechanism of action and other drugs , Fosetyl-aluminium, metrafenone, oxathiapiprolin, oxathiapiprolin, picarbutrazox, pyriofenone, terioflone, tebufloquin, triazoxide, potassium hydrogencarbonate potassium hydrogen carbonate, sodium hydrogen carbonate, shiitake mushroom mycelium extract, shiitake mushroom body extract, BCF-082 (test name), ZF-9646 (test name) and the like.

Insecticides and miticides:
A: Acetylcholinesterase (AChE) inhibitor alanicarb (alanycarb), aldicarb (aldicarb), bendiocarb (bendiocarb), benfuracarb (benfuracarb), butocarboxime (butocarboxim), carbaryl, carbofuran, carbofuran Fan (carbosulfan), ethiophencarb (ethiofencarb), fenobucarb (fenobucarb), formetanate (formetanate), furathiocarb (furathiocarb), isoprocarb (isoprocarb), methiocarb (methiocarb), mesomil (methomyl), pirimicarb (pirimicarb), thiodicarb (thiodicarb) Thiofanox, triazamate,
Acephate, azamethiphos, azamethiphos, azinphos-ethyl, azinphos-methyl, chloroethoxyfos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlormephos chlorpyrifos), chlorpyrifos-methyl, cyanophos, cyanodiphos, diazinon, dichlorvos, dimethoate, dimethylvinphos, disulfoton, EPN, fenitrothion (Fenitrothion), fenthion (fenthion), isoxathion (isoxathion), malathion (malathion), methamidophos (methamidophos), methidathion (methidathion), omethoate (omethoate), oxydimetone-methyl (oxydemeton-methy) l), parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosmet, phoxim, pirimiphos-methyl, profenofos , Prothiofos (prothiofos), pyraclofos (pyraclofos), sulfotep (sulfotep), terbufos (terbufos), tetrachlorovinphos (tetrachlorvinphos), thiometon (thiometon), trichlorfon (trichlorfon),
B: GABAergic chloride ion channel antagonist endosulfan, alpha-endosulfan,
Ethiprole, fipronil, flufiprole, pyriprole,
Afoxolaner (afoxolaner), fluralaner (fluralaner), lotilanel (lotilaner), saroraner (sarolaner),
C: sodium channel modulator acrinathrin, allethrin, allflurin, benfluthrin, bifenthrin, kappa-bifenthrin, kappa-bifenthrin, bioallethrin, bioresmethrin, chloroprrethrin ), Cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, gamma-cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, cypermethrin ), Alpha-cypermethrin, beta-cypermethrin, zeta-cypermethrin, cyphenothrin, deltamethrin Empentrin (empenthrin), esfenvalerate (esfenvalerate), etofenprox (etofenprox), fenpropatrin (fenpropathrin), fenvalerate (fenvalerate), flucitrinate (flucythrinate), flumethrin (flumethrin), fluvalinate (fluvalinate), Tau-fluvalinate, halfenprox, heptafluthrin, imiprothrin, imiprothrin, meperfluthrin, metofluthrin, metofluthrin, epsilon-methofluthrin Trim (momfluorothrin), epsilon-momfluorothrin (epsilon-momfluorothrin), permethrin (permethrin), phenothrin (phenothrin), pyrethrin (pyrethrins), resmethrin (resmethrin), silafluofen (Silafluofen), tefluthrin (tefluthrin), kappa-tefluthrin (kappa-tefluthrin), tetramethrin (tetramethrin), d-T-80-phthalthrin (d-tetramethrin), tetramethylfluthrin (tetramethylfluthrin), tralomethrin (tralomethrin), trans Transluthrin,
Methoxychlor,
D; nicotinic acetylcholine receptor (nAChR) agonist acetamiprid (acetamiprid), clothianidin (clothianidin), dinotefuran (dinotefuran), imidacloprid (imidacloprid), nitenpyram (nitenpyram), thiacloprid, thiamethoxam (thiamethoxam)
Sulfoxaflor,
Flupyradifurone,
Triflumezopyrim,
E: nicotinic acetylcholine receptor (nAChR) allosteric modulator spinetoram, spinosad,
F: glutamate-gated chloride ion channel activator abamectin (abamectin), emamectin-benzoate (emamectin-benzoate), lepimectin (lepimectin), milbemectin (milbemectin),
G: juvenile hormone analog mesoprene,
Fenoxycarb,
Pyriproxyfen,
H: Hemiptera selective feeding inhibitor pymetrozine,
Flonicamid,
I; tick growth inhibitor clofentezine, hexythiazox,
Etoxazole,
J: microorganism-derived insect midgut endometrial disruptor Bacillus thuringiensis (bacillus thuringiensis, subsp. Israelensis, subsp. Aizawai, subsp. Kurstaki, subsp. Tenenebrionis, 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 (bistrifluron), chlorfluazuron (chlorfluazuron), diflubenzuron (diflubenzuron), flucycloxuron (flucycloxuron), flufenoxuron (flufenoxuron), hexaflumuron (hexaflumuron), lufenuron (lufenuron), novaluron ), Noviflumuron, teflubenzuron, teflubenzuron, triflumuron,
O: chitin biosynthesis inhibitor (type 1)
Buprofezin,
P; molting inhibitor (fly fly insect)
Cyromazine,
Q: molting hormone (ecdysone) receptor agonist chromafenozide (chromafenozide), halofenozide (halofenozide), methoxyfenozide (methoxyfenozide), tebufenozide (tebufenozide),
R: octopamine receptor agonist amitraz,
S; mitochondrial electron transport complex III inhibitor hydramethylnon,
Acequinocyl,
Fluacrypyrim,
T: mitochondrial electron transport complex I inhibitor fenazaquin, fenpyroximate, pyrimidifen, pyridaben, pyridaben, tebufenpyrad, tolfenpyrad,
Rotenone,
U: voltage-gated sodium channel blocker indoxacarb (indoxacarb), indoxacarb-MP (indoxacarb-MP),
Metaflumizone,
V: acetyl-CoA carboxylase inhibitor spirodiclofen, spiromesifen, spirotetramat,
W: mitochondrial electron transport complex II inhibitor cyenopyrafen, cyflumetofen,
Pyflubumide,
X: ryanodine receptor modulator chlorantraniliprole, cyantraniliprole, cyclaniliprole, cyclaniliprole, cyhalodiamide, flubendiamide, flubendiamide, tetraniliprole,
And UN; mechanism of action and other drugs azadirachtin, benzoximate, bifenazate, bromopropylate, dicofol, pyridalyl, pyrifluquinazone,
Afidopyropen, broflanilide, dichlororomezotiaz, flomethoquin, flometoquin, fluhexafon, fluhexamethamide, ME5382 (test name), NA-89 (test name), NC-515 (Test name) and ZDI2501 (test name).

  Nematicides: cadusafos, dichlofenthion, ethoprophos, fenamiphos, fenamiphos, fluensulfone, fluazaindolizine, fosthiazate, fostietan (fosthiazane) (Imicyafos), isamidofos, isazofos, methyl bromide, methyl isothiocyanate, oxamyl, sodium azide, tioxazafen, BYI- 1921 (test name) and MAI-08015 (test name).

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

  Antifungals: climbazole, ketoconazole, miconazole nitrate and the like.

  Antibacterial agents: amoxicillin, ampicillin, bethoxazin, bithionol, bronopol, bronopol, cefapirin, cefazolin, cefazolin, cefquinoline, cefquinoline, cefquinoline (Chlortetracycline), clavulanic acid, danofloxacin (danofloxacin), difloxacin (difloxacin), dinitramide (dinitolmide), enrofloxacin (enrofloxacin), florfenicol (florfenicol), lincomycin, romefloxacin ( lomefloxacin), marbofloxacin, marloxacin, miloxacin, mirosamycin, nitrapyrin, norfloxacin, norfloxacin, octhilinone, ofuro Sasin (ofloxacin), orbifloxacin (orbifloxacin), oxolinic acid, oxytetracycline, oxytetracycline, penicillin, streptomycin, thiamphenicol, tiamulin fumarate Tilmicosin phosphate, tylosin acetate, tylosin phosphate, tulathromycin, valnemulin, shell calcined calcium (calcium oxide), taralomyces, Trichoderma and Coniotylium sp.

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

(Synthesis example)
Synthesis Example 1
N- [2- [2-Chloro-4- (cyclopropylethynyl) phenyl] -2-methoxy-1-methylethyl] -2- (trifluoromethyl) nicotinamide (Compound No. 3-017 of the present invention).

Step 1: Preparation of 4-bromo-2-chloro-1- (2-nitro-1-propenyl) benzene 5.78 g of ammonium acetate and 18.18 g of nitroethane were added to a solution of 6.59 g of 4-bromo-2-chlorobenzaldehyde in 30 ml of acetic acid. Then, the mixture was stirred at 90 ° C. for 2 hours and then at room temperature for 18 hours. After the reaction was completed, 200 ml of water was added to the reaction mixture, and the precipitated solid was separated by filtration and washed with 20 ml of water. Drying under reduced pressure gave 5.32 g of the desired product as yellow crystals.
Melting point 105.0-107.0 ° C
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.09 (s, 1H), 7.67 (d, J = 1.5 Hz, 1H), 7.50 (dd, J = 8.4, 1.5 Hz, 1H), 7.20 ( d, J = 8.4Hz, 1H), 2.33 (s, 3H).

Step 2: Preparation of 4-bromo-2-chloro-1- (1-methoxy-2-nitropropyl) benzene 5.37 g of 4-bromo-2-chloro-1- (2-nitro-1-propenyl) benzene 14.98 g of a 28% methanol solution of sodium methoxide was added dropwise to a 60 ml solution of toluene with stirring under ice-cooling, and after the addition was completed, the mixture was further stirred at the same temperature for 30 minutes. After completion of the reaction, acetic acid (20 ml) and water (80 ml) were added to the reaction mixture, and the mixture was extracted with ethyl acetate (200 ml × 1). The solvent was distilled off under. The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (gradient of 5:95 to 15:85) to give 5.28 g of the desired product as a yellow oil.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ7.55-7.65 (m, 1H), 7.45-7.55 (m, 1H), 7.3-7.45 (m, 1H), 5.38 and 5.16 (d, J = 3.6 and 6.3Hz, 1H), 4.65-4.8 (m, 1H), 3.31 and 3.18 (s, 3H), 1.39 and 1.36 (d, J = 6.9Hz, 3H).

Step 3: Preparation of 2- (4-bromo-2-chlorophenyl) -2-methoxy-1-methylethylamine 5.28 g of 4-bromo-2-chloro-1- (1-methoxy-2-nitropropyl) benzene It was dissolved in 20 ml of a mixed solvent of methanol and water (1: 1), and 5.50 g of ammonium chloride and 2.87 g of reduced iron were added, followed by stirring at 70 ° C. for 6 hours. After the reaction was completed, the mixture was allowed to cool to room temperature, and insoluble materials were removed by filtration through Celite, and then the solvent was distilled off under reduced pressure. To the residue was added 50 ml of a saturated aqueous solution of sodium carbonate, and the mixture was extracted with 100 ml of ethyl acetate. The organic layer was washed with 20 ml of water, dehydrated and dried in the order of saturated saline and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 4.45 g of a crude product as a yellow oily substance. This was used in the next step without further purification.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ7.54 and 7.53 (s, 1H), 7.4-7.5 (m, 1H), 7.25-7.35 (m, 1H), 4.48 and 4.34 (d, J = 4.5 and 6.6Hz, 1H), 3.25 and 3.21 (s, 3H), 3.1-3.2 and 2.95-3.05 (m, 1H), 1.01 and 1.00 (d, J = 6.6Hz, 3H).

Step 4: Preparation of tert-butyl N- [2- (4-bromo-2-chlorophenyl) -2-methoxy-1-methylethyl] carbamate 2- (4-bromo-2-chlorophenyl) -2-methoxy A mixture of 4.45 g of 1-methylethylamine in 12 ml of ethyl acetate and 3.39 g of potassium carbonate in 12 ml of water was added dropwise with stirring at room temperature, and 5.23 g of di-tert-butyl dicarbonate was added dropwise. Stirring was continued at the same temperature for another 2 hours. After the reaction was completed, 20 ml of water was added to the reaction mixture, and the mixture was extracted with ethyl acetate (20 ml × 1). The organic layer was washed with 20 ml of water, and then dehydrated and dried with saturated saline and anhydrous sodium sulfate in that order. Distilled off. The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (gradient of 0: 100 to 15:85) to obtain 4.00 g of the desired product as a pale yellow oil.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ7.5-7.55 (m, 1H), 7.35-7.45 (m, 1H), 7.2-7.35 (m, 1H), 4.6-4.85 (m, 1H) , 4.45-4.6 (m, 1H), 3.9-4.05 (m, 1H), 3.27 and 3.26 (s, 3H), 1.53 and 1.42 (s, 9H), 1.25-1.35 (m, 3H).

Step 5: Production of tert-butyl N- [2- [2-chloro-4- (cyclopropylethynyl) phenyl] -2-methoxy-1-methylethyl] carbamate N- [2- (4-bromo- To a solution of 1.0 g of tert-butyl 2-chlorophenyl) -2-methoxy-1-methylethyl] carbamate in 2 ml of N, N-dimethylformamide, 4 ml of triethylamine, 873 mg of cyclopropylacetylene, 201 mg of copper (I) iodide and tetrakis 915 mg of (triphenylphosphine) palladium (0) was added, and the mixture was stirred at 90 ° C. for 6 hours under a nitrogen atmosphere. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, 10 ml of a saturated aqueous solution of ammonium chloride was added, and the mixture was extracted with ethyl acetate (10 ml × 2). The organic layers were combined, dehydrated and dried in the order of saturated saline and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (gradient of 5:95 to 10:90) to obtain 840 mg of the desired product as a brown resin.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ7.35-7.4 (m, 1H), 7.3-7.35 (m, 1H), 7.2-7.25 (m, 1H), 4.55-4.7 (m, 1H) , 4.45-4.55 (m, 1H), 3.85-4.1 (m, 1H), 3.26 and 3.25 (s, 3H), 1.55 and 1.42 (s, 9H), 1.25-1.35 (m, 1H), 1.23 and 0.95 ( d, J = 6.9Hz, 3H), 0.75-0.95 (m, 4H).

Step 6: Preparation of 2- [2-chloro-4- (cyclopropylethynyl) phenyl] -2-methoxy-1-methylethylamine N- [2- [2-chloro-4- (cyclopropylethynyl) phenyl]- To a solution of tert-butyl 2-methoxy-1-methylethyl] carbamate (840 mg) in dichloromethane (3 ml) was added trifluoroacetic acid (1 ml) under ice-cooling and stirring, and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, the solvent was distilled off under reduced pressure, 10 ml of a 10% aqueous sodium carbonate solution was added to the residue, and the mixture was extracted with ethyl acetate (10 ml × 2). The organic layers were combined, washed with 10 ml of water, dehydrated and dried in the order of saturated saline and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 550 mg of a crude product as a brown oily substance. This was used in the next step without further purification.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ7.3-7.4 (m, 1H), 7.25-7.3 (m, 2H), 4.75-4.95 (m, 2H), 4.45-4.65 (m, 1H) , 3.9-4.1 (m, 1H), 3.26 and 3.25 (s, 3H), 1.42 (bs, 3H), 1.2-1.35 (m, 1H), 0.75-1.0 (m, 4H).

Step 7: Production of N- [2- [2-chloro-4- (cyclopropylethynyl) phenyl] -2-methoxy-1-methylethyl] -2- (trifluoromethyl) nicotinamide 2- (trifluoromethyl ) To a solution of 94 mg of nicotinic acid in 1 ml of dichloromethane were added 145 mg of oxalyl chloride and 10 mg of N, N-dimethylformamide, and the mixture was stirred at room temperature for 1 hour. Then, the solvent was distilled off under reduced pressure, the residue was dissolved in 1 ml of dichloromethane, and the mixture was stirred under ice-cooling and stirred for 2- [2-chloro-4- (cyclopropylethynyl) phenyl] -2-methoxy-1-methylethylamine. The mixture was added dropwise to a mixture of a solution of 100 mg of dichloromethane in 1 ml and a solution of potassium carbonate in 79 mg of water in 1 ml. After the addition was completed, the mixture was stirred at the same temperature for 30 minutes. After completion of the reaction, 10 ml of water was added to the reaction mixture, and the mixture was extracted with dichloromethane (10 ml × 1). The organic layer was dehydrated and dried in the order of saturated saline and anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (gradient of 0:10 to 3: 7) to obtain 24 mg of the desired product as a colorless resinous material.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.7-8.8 (m, 1H), 7.85-7.95 and 7.6-7.65 (m, 1H), 7.45-7.6 (m, 1H), 7.4-7.45 ( m, 1H), 7.3-7.35 (m, 1H), 7.2-7.25 (m, 1H), 6.26 and 6.05 (d, J = 9.9Hz, 1H), 4.75 and 4.63 (d, J = 3.9Hz, 1H) , 4.5-4.6 and 4.4-4.5 (m, 1H), 3.29 and 3.28 (s, 3H), 1.3-1.55 (m, 1H), 1.40 and 1.05 (d, J = 6.9Hz, 3H), 0.75-0.95 ( m, 4H).

Synthesis Example 2
N- [2- [2-Chloro-4- (cyclopropylethynyl) phenyl] -1-methylethyl] -2- (difluoromethyl) nicotinamide (Compound No. 3-002 of the present invention).

Step 1: Preparation of 2- (4-bromo-2-chlorophenyl) -1-methylethylamine A solution of 1.36 g of lithium aluminum hydride in 40 ml of diethyl ether under a nitrogen atmosphere was stirred at 0 ° C. under stirring at 4- ° C. A solution of 2.00 g of 2-chloro-1-[(E) -2-nitro-1-propenyl] benzene in 60 ml of diethyl ether was added dropwise over 30 minutes, and after completion of the addition, the mixture was stirred at 40 ° C. for 1 hour. After completion of the reaction, the reaction mixture was ice-cooled, 2 ml of water and 2 ml of a 1N aqueous solution of sodium hydroxide were added dropwise, and after the addition was completed, stirring was continued at the same temperature for another 30 minutes. Then, 7 ml of water was added to the reaction mixture, which was filtered through celite, and the solvent was distilled off under reduced pressure to obtain 1.60 g of a crude product as a pale yellow resinous substance. This was used in the next step without further purification.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ7.53 (d, J = 2.1 Hz, 1H), 7.33 (dd, J = 8.4, 2.1 Hz, 1H), 7.10 (d, J = 8.4 Hz, 1H), 3.1-3.4 (m, 1H), 2.79 (dd, J = 13.5, 5.4Hz, 1H), 2.63 (dd, J = 13.5, 5.4Hz, 1H), 1.13 (d, J = 9.6Hz, 3H ).

Step 2: Preparation of tert-butyl N- [2- (4-bromo-2-chlorophenyl) -1-methylethyl] carbamate 1.6 g of 2- (4-bromo-2-chlorophenyl) -1-methylethylamine 1.9 g of di-tert-butyl dicarbonate and 874 mg of triethylamine were added to a solution of 10 ml of dichloromethane, and the mixture was stirred at room temperature for 16 hours. After the reaction was completed, 20 ml of water was added to the reaction mixture, the organic layer was separated, and the aqueous layer was extracted with chloroform (10 ml × 1). The organic layers were combined, washed with water (10 ml × 1), dehydrated and dried in the order of saturated saline and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was washed with hexane to obtain 2.1 g of the desired product as white crystals.
77.0-80.0 ° C
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ7.51 (d, J = 2.4 Hz, 1H), 7.31 (dd, J = 8.4, 2.4 Hz, 1H), 7.10 (d, J = 8.4 Hz, 1H), 4.2-4.55 (m, 1H), 3.85-4.1 (m, 1H), 2.84 (d, J = 6.6Hz, 2H), 1.38 (s, 9H), 1.15 (d, J = 6.6Hz, 3H ).

Step 3: Preparation of tert-butyl N- [2- [2-chloro-4- (cyclopropylethynyl) phenyl] -1-methylethyl] carbamate N- [2- (4-bromo-2-chlorophenyl) To a solution of 1.5 g of tert-butyl-1-methylethyl] carbamate in 3 ml of N, N-dimethylformamide, 4 ml of triethylamine, 1.4 g of cyclopropylacetylene, 328 mg of copper (I) iodide and palladium tetrakis (triphenylphosphine) (0) 1.5 g was added and the mixture was stirred at 100 ° C. for 6 hours under a nitrogen atmosphere. After the reaction was completed, the reaction mixture was allowed to cool to room temperature, 10 ml of a saturated aqueous ammonium chloride solution was added, and the mixture was extracted with ethyl acetate (10 ml × 1). The organic layer was dehydrated and dried in the order of saturated saline and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (gradient of 5:95 to 10:90) to give 1.1 g of the desired product as a brown resinous material.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ7.25-7.4 (m, 1H), 7.05-7.25 (m, 2H), 4.41 (bs, 1H), 3.85-4.1 (m, 1H), 2.75 -3.0 (m, 2H), 1.4-1.5 (m, 1H), 1.38 (s, 9H), 1.13 (d, J = 6.6Hz, 3H), 0.75-0.95 (m, 4H).

Step 4: Preparation of 2- [3-chloro-4- (cyclopropylethynyl) phenyl] -1-methylethylamine N- [2- [2-chloro-4- (cyclopropylethynyl) phenyl] -1-methylethyl 3 ml of trifluoroacetic acid was added to a solution of 410 mg of tert-butyl carbamic acid in 5 ml of dichloromethane, and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, the solvent was distilled off under reduced pressure, 10 ml of a 10% aqueous potassium carbonate solution was added to the residue, and the mixture was extracted with ethyl acetate (10 ml × 2). The organic layers were combined, washed with 10 ml of water, dehydrated and dried in the order of a saturated saline solution and anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 233 mg of a crude product as a brown oily substance. This was used in the next step without further purification.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ7.55-7.8 (m, 1H), 7.35-7.45 (m, 1H), 7.05-7.2 (m, 1H), 3.55-3.8 (m, 1H) , 2.75-3.3 (m, 2H), 1.35-1.5 (m, 1H), 1.32 (bs, 3H), 0.75-0.95 (m, 4H).

Step 5: Production of N- [2- [2-chloro-4- (cyclopropylethynyl) phenyl] -1-methylethyl] -2- (difluoromethyl) nicotinamide 55 mg of 2- (difluoromethyl) nicotinic acid in dichloromethane To 1 ml of the solution, 57 mg of oxalyl chloride and 10 mg of N, N-dimethylformamide were added, and the mixture was stirred at room temperature for 1 hour. Subsequently, the solvent was distilled off under reduced pressure, the residue was dissolved in 1 ml of dichloromethane, and 70 mg of 2- [3-chloro-4- (cyclopropylethynyl) phenyl] -1-methylethylamine and 61 mg of triethylamine were stirred under ice-cooling and stirring. Was added dropwise to a solution of 2 ml of dichloromethane. After completion of the dropwise addition, stirring was continued at the same temperature for 30 minutes, and then 10 ml of water was added to the reaction mixture, followed by extraction with dichloromethane (10 ml × 1). The organic layer was dehydrated and dried in the order of saturated saline and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (0:10 to 3: 7) to give 24 mg of the desired product as brown crystals.
113.0-115.0 ° C
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.65-8.75 (m, 1H), 7.7-7.8 (m, 1H), 7.4-7.5 (m, 1H), 7.35-7.4 (m, 1H) , 7.15-7.25 (m, 2H), 6.88 (t, J = 54.7Hz, 1H), 5.97 (bs, 1H), 4.4-4.65 (m, 1H), 2.8-3.15 (m, 2H), 1.35-1.5 (m, 1H), 1.30 (d, J = 6.3Hz, 3H), 0.75-0.95 (m, 4H).

Synthesis Example 3
2-Chloro-N- [2- [2-chloro-4- (3-furylethynyl) phenyl] -1-methylethyl] nicotinamide (Compound No. 3-006 of the present invention).

Step 1: Production of tert-butyl N- [2- [2-chloro-4- (3-furylethynyl) phenyl] -1-methylethyl] carbamate N- [produced in Step 2 of Synthesis Example 2 To a solution of 700 mg of tert-butyl 2- (4-bromo-2-chlorophenyl) -1-methylethyl] carbamate in 2 ml of N, N-dimethylformamide, 303 mg of triethylamine, 394 mg of (3-furylethynyl) trimethylsilane, copper iodide 76 mg of (I), 70 mg of dichlorobis (triphenylphosphine) palladium (II) and 2.4 ml of tetrabutylammonium fluoride were added, and the mixture was stirred at 80 ° C. for 4 hours under a nitrogen atmosphere. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, 10 ml of a saturated aqueous solution of ammonium chloride and 10 ml of ethyl acetate were added, and the mixture was filtered through celite. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate (10 ml × 1). The organic layers were combined, dehydrated and dried in the order of saturated saline and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (gradient of 5:95 to 10:90) to obtain 460 mg of the desired product as brown crystals.
Melting point 58.0-60.0 ° C
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ7.65-7.7 (m, 1H), 7.45-7.55 (m, 1H), 7.40 (t, J = 1.7 Hz, 1H), 7.25-7.35 (m , 1H), 7.0-7.25 (m, 1H), 6.50 (d, J = 2.0Hz, 1H), 4.40 (bs, 1H), 3.9-4.05 (m, 1H), 2.8-3.0 (m, 2H), 1.38 (bs, 9H), 1.15 (d, J = 6.5Hz, 3H).

Step 2: Preparation of 2- [3-chloro-4- (3-furylethynyl) phenyl] -1-methylethylamine N- [2- [2-chloro-4- (3-furylethynyl) phenyl] -1- To a solution of tert-butyl methylethyl] carbamate (460 mg) in dichloromethane (2 ml) was added trifluoroacetic acid (1 ml), and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, the solvent was distilled off under reduced pressure, 10 ml of a 10% aqueous potassium carbonate solution was added to the residue, and the mixture was extracted with ethyl acetate (10 ml × 2). The organic layers were combined, washed with 10 ml of water, dehydrated and dried in the order of saturated saline and anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 210 mg of a crude target product as a brown resinous substance. Was. This was used in the next step without further purification.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ7.65-7.7 (m, 1H), 7.45-7.55 (m, 1H), 7.4-7.45 (m, 1H), 7.25-7.35 (m, 1H) , 7.15-7.25 (m, 1H), 7.10 (d, J = 7.8Hz, 1H), 3.2-3.35 (m, 1H), 2.6-2.95 (m, 2H), 1.86 (bs, 2H), 1.1-1.2 (m, 3H).

Step 3: Production of 2-chloro-N- [2- [2-chloro-4- (3-furylethynyl) phenyl] -1-methylethyl] nicotinamide 2- [3-chloro-4- (3-furyl) In a solution of 70 mg of [ethynyl) phenyl] -1-methylethylamine in 1 ml of N, N-dimethylformamide, 47 mg of 2-chloronicotinic acid, 0.5 ml of triethylamine, 5 mg of N, N-dimethyl-4-aminopyridine and 5 mg of O- (1-benzoic acid). 112 mg of triazolyl) -N, N, N ', N',-tetramethyluronium tetrafluoroborate was added, and the mixture was stirred at room temperature for 16 hours. After completion of the reaction, 10 ml of water was added to the reaction mixture, and the mixture was extracted with 10 ml of ethyl acetate. The organic layer was washed with a 1N aqueous hydrochloric acid solution (10 ml × 2), dehydrated and dried in the order of saturated saline and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (3: 7 to 5: 5 gradient) to give 45 mg of the desired product as a brown resin.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.4-8.5 (m, 1H), 7.9-8.0 (m, 1H), 7.65-7.7 (m, 1H), 7.51 (dd, J = 9.2, 1.7Hz, 1H), 7.40 (t, J = 1.7Hz, 1H), 7.25-7.4 (m, 2H), 7.15-7.25 (m, 1H), 6.5-6.55 (m, 1H), 6.36 (d, J = 8.5Hz, 1H), 4.45-4.65 (m, 1H), 2.9-3.15 (m, 2H), 1.33 (d, J = 6.5Hz, 3H).

Synthesis Example 4
3-chloro-N- [2- [2-chloro-4-[(6-fluoropyridin-3-yl) ethynyl] phenyl] -1-methylethyl] -2-pyridinecarboxamide (Compound No. 2- 004).

Step 1: Production of tert-butyl N- [2- [2-chloro-4- (trimethylsilylethynyl) phenyl] -1-methylethyl] carbamate N- [2- produced in Step 2 of Synthesis Example 2 To a solution of 1.0 g of tert-butyl (4-bromo-2-chlorophenyl) -1-methylethyl] carbamate in 3 ml of N, N-dimethylformamide, 435 mg of triethylamine, 422 mg of trimethylsilylacetylene, 109 mg of copper (I) iodide and 109 mg of dichlorobis 201 mg of (triphenylphosphine) palladium (II) was added, and the mixture was stirred at 100 ° C. for 4 hours under a nitrogen atmosphere. After the reaction was completed, the reaction mixture was allowed to cool to room temperature, 10 ml of a saturated aqueous ammonium chloride solution was added, and the mixture was extracted with ethyl acetate (10 ml × 1). The organic layer was dehydrated and dried in the order of saturated saline and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (gradient of 5:95 to 10:90) to obtain 900 mg of the desired product as brown crystals.
74.0-76.0 ° C
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ7.46 (d, J = 1.7 Hz, 1H), 7.28 (d, J = 1.7 Hz, 1H), 7.1-7.2 (m, 1H), 4.3- 4.55 (m, 1H), 3.85-4.05 (m, 1H), 2.8-2.95 (m, 2H), 1.38 (s, 9H), 1.13 (d, J = 6.5Hz, 3H), 0.23 (s, 9H) .

Step 2: Production of tert-butyl N- [2- [2-chloro-4-[(6-fluoropyridin-3-yl) ethynyl] phenyl] -1-methylethyl] carbamate N- [2- [ To a solution of 450 mg of tert-butyl 2-chloro-4- (trimethylsilylethynyl) phenyl] -1-methylethyl] carbamate in 2 ml of N, N-dimethylformamide, 373 mg of triethylamine, 328 mg of 2-fluoro-5-iodopyridine, iodide 47 mg of copper (I), 71 mg of tetrakis (triphenylphosphine) palladium (0) and 1.47 ml of tetrabutylammonium fluoride were added, and the mixture was stirred at 80 ° C. for 4 hours under a nitrogen atmosphere. After the reaction was completed, the reaction mixture was allowed to cool to room temperature, 10 ml of a saturated aqueous ammonium chloride solution was added, and the mixture was extracted with ethyl acetate (10 ml × 1). The organic layer was dehydrated and dried in the order of saturated saline and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (gradient of 5:95 to 10:90) to obtain 452 mg of the desired product as a brown resin.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.37 (d, J = 2.4 Hz, 1H), 7.8-7.95 (m, 1H), 7.53 (d, J = 1.4 Hz, 1H), 7.3- 7.4 (m, 2H), 6.9-6.95 (m, 1H), 4.42 (bs, 1H), 3.95-4.05 (m, 1H), 2.91 (d, J = 6.1Hz, 2H), 1.38 (s, 9H) , 1.17 (d, J = 6.8Hz, 3H).

Step 3: Preparation of 2- [3-chloro-4-[(6-fluoropyridin-3-yl) ethynyl] phenyl] -1-methylethylamine N- [2- [2-chloro-4-[(6- To a solution of tert-butyl fluoropyridin-3-yl) ethynyl] phenyl] -1-methylethyl] carbamate (452 mg) in dichloromethane (2 ml) was added trifluoroacetic acid (1 ml), and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, the solvent was distilled off under reduced pressure, 10 ml of a 10% aqueous potassium carbonate solution was added to the residue, and the mixture was extracted with ethyl acetate (10 ml × 2). The organic layers were combined, washed with 10 ml of water, dehydrated and dried in the order of a saturated saline solution and anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 340 mg of the crude target product as a yellow resinous substance. Was. This was used in the next step without further purification.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 8.35-8.4 (m, 1H), 7.85-7.95 (m, 1H), 7.54 (d, J = 1.7 Hz, 1H), 7.3-7.45 (m , 1H), 7.15-7.25 (m, 1H), 6.9-7.0 (m, 1H), 3.25-3.5 (m, 1H), 2.8-2.95 (m, 1H), 2.65-2.8 (m, 1H), 1.55 (bs, 2H), 1.16 (bs, 3H).

Step 4: Preparation of 3-chloro-N- [2- [2-chloro-4-[(6-fluoropyridin-3-yl) ethynyl] phenyl] -1-methylethyl] -2-pyridinecarboxamide 2- [ In a solution of 100 mg of 3-chloro-4-[(6-fluoropyridin-3-yl) ethynyl] phenyl] -1-methylethylamine in 1 ml of N, N-dimethylformamide 44 mg of 3-chloro-2-pyridinecarboxylic acid and 1 ml of triethylamine , N, N-dimethyl-4-aminopyridine (5 mg) and O- (1-benzotriazolyl) -N, N, N ′, N ′,-tetramethyluronium tetrafluoroborate (107 mg), and the mixture was brought to room temperature. And stirred for 16 hours. After completion of the reaction, 10 ml of water was added to the reaction mixture, and the mixture was extracted with 10 ml of ethyl acetate. The organic layer was washed with a 1N aqueous hydrochloric acid solution (10 ml × 2), dehydrated and dried in the order of saturated saline and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (3: 7 to 5: 5 gradient) to give 81 mg of the desired product as white crystals.
Melting point 161.0-163.0 ° C
_{^{1 H NMR (CDCl 3, Me}} 4 Si, 300MHz) δ8.45 (dd, J = 4.4, 1.4Hz, 1H), 8.36 (d, J = 2.4Hz, 1H), 7.8-7.9 (m, 1H), 7.75-7.8 (m, 2H), 7.53 (s, 1H), 7.3-7.4 (m, 3H), 6.93 (dd, J = 8.5, 3.1Hz, 1H), 4.45-4.55 (m, 1H), 2.95- 3.2 (m, 2H), 1.31 (d, J = 6.8Hz, 3H).

Synthesis Example 5
N- [2- [2-chloro-4-[(6-fluoropyridin-3-yl) ethynyl] phenyl] -2,2-difluoroethyl] -3-trifluoromethyl-2-pyridinecarboxamide (the compound of the present invention) No.2-010).

Step 1: Preparation of ethyl 2- (4-bromo-2-chlorophenyl) -2,2-difluoroacetate 3.20 g of 4-bromo-2-chloro-1-iodobenzene and ethyl bromodifluoroacetate under a nitrogen atmosphere. 4.40 g of copper was added to a solution of 25 g of dimethyl sulfoxide in 20 ml and stirred at 60 ° C. for 2 hours and then at room temperature for 16 hours. After the reaction was completed, 30 ml of a saturated aqueous solution of ammonium chloride was added to the reaction mixture, which was filtered through celite, and the filtrate was extracted with 20 ml of diethyl ether. The organic layer was dehydrated and dried in the order of saturated saline and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (0:10 to 2: 8) to give 2.40 g of the desired product as a brown resin.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ7.45-7.6 (m, 3H), 4.25-4.4 (m, 2H), 1.2-1.35 (m, 3H).

Step 2: Production of 2- (4-bromo-2-chlorophenyl) -2,2-difluoroacetic acid amide 2.4 g of 2- (4-bromo-2-chlorophenyl) -2,2-difluoroacetic acid in 4% ammonia It was dissolved in 20 ml of a methanol solution and stirred at room temperature for 16 hours. After completion of the reaction, the solvent was distilled off under reduced pressure to obtain 2.1 g of the desired product as white crystals.
158.0-160.0 ° C
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ7.55-7.65 (m, 2H), 7.45-7.55 (m, 1H), 6.51 (bs, 1H), 6.14 (bs, 1H).

Step 3: Preparation of 2- (4-bromo-2-chlorophenyl) -2,2-difluoroethylamine A solution of 2.0 g of 2- (4-bromo-2-chlorophenyl) -2,2-difluoroacetic acid amide in 5 ml of tetrahydrofuran is added. Under ice-cooling and stirring, 40 ml of an 8.5% tetrahydrofuran solution of a borane-tetrahydrofuran complex was added dropwise. After completion of the addition, stirring was continued at the same temperature for 30 minutes and then at 70 ° C. for 2 hours. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, 20 ml of a saturated aqueous solution of sodium hydrogen carbonate was added, and the mixture was extracted with ethyl acetate (20 ml × 2). The organic layer was dehydrated and dried in the order of saturated saline and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 1.5 g of a crude target product as a pale yellow resinous substance. This was used in the next step without further purification.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ7.55-7.7 (m, 1H), 7.4-7.6 (m, 2H), 3.15-3.7 (m, 2H).

Step 4: Preparation of tert-butyl N- [2- (4-bromo-2-chlorophenyl) -2,2-difluoroethyl] carbamate 2- (4-bromo-2-chlorophenyl) -2,2-difluoro To a solution of 1.50 g of ethylamine in 5 ml of dichloromethane were added 1.50 g of di-tert-butyl dicarbonate and 0.85 g of triethylamine, and the mixture was stirred at room temperature for 16 hours. After completion of the reaction, 10 ml of water was added to the reaction mixture, the organic layer was separated, and the aqueous layer was extracted with ethyl acetate (20 ml × 1). The organic layers were combined, dehydrated and dried in the order of saturated saline and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (gradient of 0: 100 to 25:75) to obtain 0.82 g of the desired product as a yellow resin.
_{^{1 H NMR (CDCl 3, Me}} 4 Si, 300MHz) δ7.62 (bs, 1H), 7.45 (bs, 2H), 4.7-4.9 (m, 1H), 3.85-4.05 (m, 2H), 1.35 (s , 9H).

Step 5: Production of tert-butyl N- [2- [2-chloro-4- (trimethylsilylethynyl) phenyl] -2,2-difluoroethyl] carbamate N- [2- (4-bromo-2-chlorophenyl) ) -2,2-Difluoroethyl] tert-butylcarbamate (820 mg) in N, N-dimethylformamide (2 ml), triethylamine (0.4 ml), trimethylsilylacetylene (327 mg), copper (I) iodide (85 mg) and dichlorobis (triphenylphosphine) palladium (II) 78 mg was added, and the mixture was stirred at 60 ° C. for 3 hours under a nitrogen atmosphere. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, 5 ml of a saturated aqueous solution of ammonium chloride was added, and the mixture was extracted with ethyl acetate (10 ml × 1). The organic layer was dehydrated and dried in the order of saturated saline and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (0: 100 to 25:75 gradient) to obtain 500 mg of the desired product as a brown resin.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ7.45-7.55 (m, 2H), 7.3-7.4 (m, 1H), 4.7-4.85 (m, 1H), 3.8-4.05 (m, 2H) , 1.35 (s, 9H), 0.23 (s, 9H).

Step 6: Preparation of tert-butyl N- [2- [2-chloro-4-[(6-fluoropyridin-3-yl) ethynyl] phenyl] -2,2-difluoroethyl] carbamate N- [2 To a solution of 500 mg of tert-butyl- [2-chloro-4- (trimethylsilylethynyl) phenyl] -2,2-difluoroethyl] carbamate in 2 ml of toluene, 0.4 ml of triethylamine, 346 mg of 2-fluoro-5-iodopyridine, iodine 49 mg of copper (I) chloride, 45 mg of dichlorobis (triphenylphosphine) palladium (II) and 1.5 ml of a 1M solution of tetrabutylammonium fluoride in tetrahydrofuran were added, and the mixture was stirred under a nitrogen atmosphere at room temperature for 2 hours. After completion of the reaction, 5 ml of a saturated ammonium chloride aqueous solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate (10 ml × 1). The organic layer was dehydrated and dried in the order of saturated saline and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (gradient of 0: 100 to 25:75) to obtain 330 mg of the desired product as a brown resinous material.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.39 (s, 1H), 7.85-7.95 (m, 1H), 7.55-7.65 (m, 2H), 7.4-7.5 (m, 1H), 6.96 (dd, J = 8.3, 3.1Hz, 1H), 4.7-4.95 (m, 1H), 3.97 (td, J = 14.2, 6.3Hz, 2H), 1.35 (s, 9H).

Step 7: Preparation of 2- [3-chloro-4-[(6-fluoropyridin-3-yl) ethynyl] phenyl] -2,2-difluoroethylamine N- [2- [2-chloro-4-[( 1 ml of trifluoroacetic acid was added to a solution of 330 mg of tert-butyl 6-fluoropyridin-3-yl) ethynyl] phenyl] -2,2-difluoroethyl] carbamate in 2 ml of dichloromethane, and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, the solvent was distilled off under reduced pressure, 10 ml of a 10% aqueous potassium carbonate solution was added to the residue, and the mixture was extracted with ethyl acetate (10 ml × 2). The organic layers were combined, washed with 10 ml of water, dehydrated and dried in the order of a saturated saline solution and anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 300 mg of a crude target product as a yellow resinous substance. Was. This was used in the next step without further purification.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.39 (s, 1H), 7.8-7.95 (m, 1H), 7.45-7.65 (m, 3H), 6.9-7.0 (m, 1H), 3.3 -3.45 (m, 2H), 1.44 (bs, 2H).

Step 8; of N- [2- [2-chloro-4-[(6-fluoropyridin-3-yl) ethynyl] phenyl] -2,2-difluoroethyl] -3-trifluoromethyl-2-pyridinecarboxamide Production 2- [3-Chloro-4-[(6-fluoropyridin-3-yl) ethynyl] phenyl] -2,2-difluoroethylamine was added to 3-trifluoromethyl-2 in a solution of 100 mg of N, N-dimethylformamide in 2 ml. -67 mg of pyridinecarboxylic acid, 65 mg of triethylamine, 5 mg of N, N-dimethyl-4-aminopyridine and O- (1-benzotriazolyl) -N, N, N ', N',-tetramethyluronium tetrafluoroborate 123 mg was added and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, 10 ml of water was added to the reaction mixture, and the mixture was extracted with 10 ml of dichloromethane. The organic layer was washed with a 1N aqueous hydrochloric acid solution (10 ml × 2), dehydrated and dried in the order of saturated saline and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (2: 8 to 5: 5 gradient) to obtain 67 mg of the desired product as white crystals.
124.0-126.0 ° C
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 8.73 (d, J = 4.8 Hz, 1H), 8.39 (s, 1H), 8.16 (d, J = 7.8 Hz, 1H), 8.0-8.15 ( m, 1H), 7.85-7.95 (m, 1H), 7.55-7.7 (m, 3H), 7.44 (d, J = 8.2Hz, 1H), 6.9-7.0 (m, 1H), 4.33 (td, J = 14.8, 6.5Hz, 2H).

Synthesis Example 6
N- [2- [2-chloro-4-[[6- (trifluoromethyl) pyridin-3-yl] ethynyl] phenyl] -2,2-difluoro-1-methylethyl] -3-trifluoromethyl- 2-pyridinecarboxamide (Compound No. 2-015 of the present invention).

Step 1: Production of 2- (4-bromo-2-chlorophenyl) -2,2-difluoroacetonitrile 2- (4-bromo-2-chlorophenyl) -2,2-difluoro produced in Step 2 of Synthesis Example 5 To a solution of 3.80 g of acetic amide and 4.77 g of pyridine in 30 ml of tetrahydrofuran, 5.63 g of trifluoroacetic anhydride was added dropwise with stirring under ice-cooling, followed by stirring at the same temperature for 1 hour. After completion of the reaction, 20 ml of water was added to the reaction mixture, and the mixture was extracted with 20 ml of ethyl acetate. The organic layer was washed with 20 ml of water and then with 20 ml of a saturated aqueous solution of sodium hydrogencarbonate, dehydrated and dried in the order of saturated saline and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 3.20 g of the crude product. Obtained as a brown resinous material. This was used in the next step without further purification.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ7.65-7.8 (m, 1H), 7.5-7.6 (m, 2H).

Step 2: Preparation of 2- (4-bromo-2-chlorophenyl) -2,2-difluoro-1-methylethylamine 1.8 g of 2- (4-bromo-2-chlorophenyl) -2,2-difluoroacetonitrile To a solution of 10 ml of ether, 5 ml of a 35% solution of methylmagnesium bromide in diethyl ether was added dropwise with stirring under ice-cooling, and the mixture was stirred at the same temperature for 1 hour. Then, 10 ml of methanol was added dropwise to the reaction mixture under ice-cooling and stirring, followed by stirring for 30 minutes. 1.1 g of sodium borohydride was added in three portions, and stirring was continued at the same temperature for another 5 hours. did. After completion of the reaction, the solvent was distilled off under reduced pressure. To the residue was added a saturated ammonium chloride aqueous solution (20 ml), and the mixture was extracted with ethyl acetate (10 ml × 2). The organic layers were combined, washed with water (20 ml × 1), dehydrated and dried in the order of saturated saline and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 1.5 g of a crude product as a brown resinous substance. . This was used in the next step without further purification.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ7.55-7.65 (m, 1H), 7.35-7.5 (m, 2H), 3.55-3.85 (m, 1H), 1.15-1.4 (m, 2H) , 1.0-1.15 (m, 3H).

Step 3: Preparation of tert-butyl N- [2- (4-bromo-2-chlorophenyl) -2,2-difluoro-1-methylethyl] carbamate 2- (4-bromo-2-chlorophenyl) -2 1.50 g of di-tert-butyl dicarbonate and 1.60 g of triethylamine were added to 1.50 g of 1,2-difluoro-1-methylethylamine in 5 ml of dichloromethane, and the mixture was stirred at room temperature for 16 hours. After the completion of the reaction, 10 ml of water was added to the reaction mixture, and the mixture was extracted with ethyl acetate (20 ml × 1). The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (0: 100 to 25:75 gradient) to give 1.15 g of the desired product as a yellow resin.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ7.55-7.65 (m, 1H), 7.3-7.5 (m, 2H), 4.55-4.8 (m, 2H), 1.15-1.35 (m, 12H) .

Step 4: Production of tert-butyl N- [2- [2-chloro-4- (trimethylsilylethynyl) phenyl] -2,2-difluoro-1-methylethyl] carbamate N- [2- (4-bromo To a solution of 900 mg of tert-butyl-2-chlorophenyl) -2,2-difluoro-1-methylethyl] carbamate in 2 ml of N, N-dimethylformamide, 0.4 ml of triethylamine, 346 mg of trimethylsilylacetylene, 90 mg of copper (I) iodide And 82 mg of dichlorobis (triphenylphosphine) palladium (II), and the mixture was stirred at 60 ° C. for 3 hours under a nitrogen atmosphere. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, 5 ml of a saturated aqueous solution of ammonium chloride was added, and the mixture was extracted with ethyl acetate (10 ml × 1). The organic layer was dehydrated and dried in the order of saturated saline and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (0: 100 to 25:75 gradient) to obtain 540 mg of the desired product as a brown resin.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ7.3-7.8 (m, 3H), 4.6-4.9 (m, 1H), 4.64 (bs, 1H), 1.1-1.45 (m, 12H), 0.23 (s, 9H).

Step 5: N- [2- [2-chloro-4-[[6- (trifluoromethyl) pyridin-3-yl] ethynyl] phenyl] -2,2-difluoro-1-methylethyl] carbamic acid-tert Preparation of -butyl Triethylamine was added to a solution of 1.60 g of tert-butyl N- [2- [2-chloro-4- (trimethylsilylethynyl) phenyl] -2,2-difluoro-1-methylethyl] carbamate in 4 ml of toluene. 0.2 ml, 5-bromo-2- (trifluoromethyl) pyridine (1.08 g), copper (I) iodide (152 mg), dichlorobis (triphenylphosphine) palladium (II) (140 mg) and 346 mg of a 1 M solution of tetrabutylammonium fluoride in tetrahydrofuran. The mixture was stirred at room temperature under a nitrogen atmosphere for 16 hours. After completion of the reaction, 5 ml of a saturated ammonium chloride aqueous solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate (10 ml × 1). The organic layer was dehydrated and dried in the order of saturated saline and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (0: 100 to 25:75 gradient) to obtain 450 mg of the desired product as a brown resin.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.7-8.9 (m, 1H), 7.9-8.05 (m, 1H), 7.65-7.8 (m, 1H), 7.35-7.6 (m, 3H) , 4.65-4.95 (m, 1H), 4.5-4.65 (m, 1H), 1.15-1.4 (m, 12H).

Step 6: Production of 2- [2-chloro-4-[[6- (trifluoromethyl) pyridin-3-yl] ethynyl] phenyl] -2,2-difluoro-1-methylethylamine N- [2- [ To a solution of 450 mg of tert-butyl 2-chloro-4-[[6- (trifluoromethyl) pyridin-3-yl] ethynyl] phenyl] -2,2-difluoro-1-methylethyl] carbamate in 3 ml of dichloromethane was added triethylamine. 1 ml of fluoroacetic acid was added, and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, the solvent was distilled off under reduced pressure, 10 ml of a 10% aqueous potassium carbonate solution was added to the residue, and the mixture was extracted with ethyl acetate (10 ml × 2). The organic layers were combined, washed with 10 ml of water, dehydrated and dried in the order of saturated saline and anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 390 mg of the crude target product as a brown resinous substance. Was. This was used in the next step without further purification.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.75-8.85 (m, 1H), 7.85-8.0 (m, 1H), 7.65-7.75 (m, 1H), 7.4-7.6 (m, 3H) , 3.65-3.95 (m, 1H), 1.3-1.45 (m, 2H), 1.05-1.15 (m, 3H).

Step 7: N- [2- [2-chloro-4-[[6- (trifluoromethyl) pyridin-3-yl] ethynyl] phenyl] -2,2-difluoro-1-methylethyl] -3-tri Preparation of fluoromethyl-2-pyridinecarboxamide 130 mg of 2- [2-chloro-4-[[6- (trifluoromethyl) pyridin-3-yl] ethynyl] phenyl] -2,2-difluoro-1-methylethylamine 74 ml of 3-trifluoromethyl-2-pyridinecarboxylic acid, 0.5 ml of triethylamine, 5 mg of N, N-dimethyl-4-aminopyridine and 5 mg of O- (1-benzotriazolyl) -N, N, N ', N',-Tetramethyluronium tetrafluoroborate (170 mg) was added, and the mixture was stirred at room temperature for 16 hours. After completion of the reaction, 10 ml of water was added to the reaction mixture, and the mixture was extracted with 10 ml of ethyl acetate. The organic layer was washed with a 1N aqueous hydrochloric acid solution (10 ml × 2), dehydrated and dried in the order of saturated saline and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (0: 100 to 25:75 gradient) to obtain 41 mg of the desired product as a colorless resinous material.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.82 (d, J = 1.8 Hz, 1H), 8.73 (dd, J = 4.8, 1.4 Hz, 1H), 8.13 (dd, J = 8.1, 1.2 Hz, 1H), 7.9-8.0 (m, 1H), 7.87 (d, J = 9.8Hz, 1H), 7.68 (dd, J = 8.1, 0.8Hz, 1H), 7.5-7.65 (m, 3H), 7.41 (dd, J = 8.1, 1.4Hz, 1H), 5.25-5.5 (m, 1H), 1.39 (d, J = 7.1Hz, 3H).

  The compound of the present invention can be produced according to the above production methods and Examples. Examples of the alkynylphenyl-substituted amide compounds included in the present invention produced in the same manner as in Synthesis Examples 1 to 6 are shown in Tables 3 to 7, and examples of their intermediates are shown in Tables 8 and 9. As shown in Table 9, alkynylphenyl-substituted amide compounds included in the present invention and intermediates for producing them are not limited to these.

In the table, c-Pr represents cyclopropyl, Ph represents phenyl, respectively.
In the table, the aromatic heterocycles represented by D-1-2a to D-25-3a represent the following structures, respectively.

The number representing the substitution position of the substituent (Z) _n corresponds to the position of the number described in the above structural formula, and for example, in the table, `` (D-23-2b) -6- The description "F" represents "6-fluoropyridin-3-yl",
In the table, the description "* 1" in the column of the melting point means that the property of the compound was oily or resinous.
Table 3

――――――――――――――――――――――――――――――――――――――――
No. X ¹ R ³ R ¹ R ² Y ¹ R ⁶ Y ² mp (℃)
――――――――――――――――――――――――――――――――――――――――
1-001 CF ₃ CH ₃ HH Cl c-Pr H 125.0-128.0
1-002 CF ₃ CH ₃ HH Cl c-Pr Cl 166.5-167.5
1-003 CF ₃ CH ₃ OCH ₃ H Cl c-Pr H * 1
1-004 CF ₃ CH ₃ OCH ₃ H Cl Ph-4-FH * 1
1-005 CF ₃ HFF Cl (D-23-1b) -5-CF ₃ H 147.0-150.0
1-006 CF ₃ HFF Cl (D-23-2b) -6-CF ₃ H 140.0-142.0
1-007 CF ₃ CH ₃ FF Cl D-1-2a H 99.0-101.0
1-008 CF ₃ CH ₃ FF Cl (D-23-1b) -5-CF ₃ H 161.0-163.0
1-009 CF ₃ CH ₃ FF Cl (D-23-2b) -6-CF ₃ H * 1
――――――――――――――――――――――――――――――――――――――――
Table 4

――――――――――――――――――――――――――――――――――――――――
No. X ¹ R ³ R ¹ R ² Y ¹ R ⁶ Y ² mp (℃)
――――――――――――――――――――――――――――――――――――――――
2-001 CF ₃ CH ₃ HH Cl c-Pr Cl 97.0-102.0
2-002 Cl CH ₃ HH Cl D-2-2a H 145.0-146.0
2-003 CF ₃ CH ₃ HH Cl (D-6-2a) -1-CH ₃ H 149.0-151.0
2-004 Cl CH ₃ HH Cl (D-23-2b) -6-FH 161.0-163.0
2-005 Cl CH ₃ HH Cl D-23-2c H 171.0-172.0
2-006 CF ₃ CH ₃ HH Cl D-25-3a H 158.0-159.0
2-007 CF ₃ CH ₃ OCH ₃ H Cl c-Pr H * 1
2-008 CF ₃ HFF Cl (D-23-1b) -5-CF ₃ H 156.0-158.0
2-009 Cl HFF Cl (D-23-2b) -6-FH 177.0-179.0
2-010 CF ₃ HFF Cl (D-23-2b) -6-FH 124.0-126.0
2-011 CF ₃ HFF Cl (D-23-2b) -6-CF ₃ H * 1
2-012 CF ₃ CH ₃ HH Cl (D-6-3a) -1-CH ₃ H 125.0-127.0
2-013 CF ₃ CH ₃ HH Cl (D-23-2b) -6-FH 124.0-126.0
2-014 CF ₃ CH ₃ FF Cl (D-23-1b) -5-CF ₃ H 131.0-133.0
2-015 CF ₃ CH ₃ FF Cl (D-23-2b) -6-CF ₃ H * 1
――――――――――――――――――――――――――――――――――――――――
Table 5

――――――――――――――――――――――――――――――――――――――――
No. X ¹ R ³ R ¹ R ² Y ¹ R ⁶ Y ² mp (℃)
――――――――――――――――――――――――――――――――――――――――
3-001 Cl CH ₃ HH Cl c-Pr H * 1
3-002 CHF ₂ CH ₃ HH Cl c-Pr H 113.0-115.0
3-003 CF ₃ CH ₃ HH Cl c-Pr H * 1
3-004 Cl CH ₃ HH Cl c-Pr Cl 40.0-42.0
3-005 CHF ₂ CH ₃ HH Cl c-Pr Cl 160.0-162.0
3-006 Cl CH ₃ HH Cl D-1-2a H * 1
3-007 Cl CH ₃ HH Cl D-2-2a H 150.0-152.0
3-008 Cl CH ₃ HH Cl (D-6-2a) -1-CH ₃ H 137.0-139.0
3-009 Cl CH ₃ HH Cl (D-6-2b) -1-CH ₃ -3-CF ₃ H * 1
3-010 Cl CH ₃ HH Cl (D-23-2b) -6-FH 148.0-149.0
3-011 CHF ₂ CH ₃ HH Cl (D-23-2b) -6-FH 138.0-140.0
3-012 Cl CH ₃ HH Cl D-23-2c H 149.0-151.0
3-013 SO ₂ CH ₃ CH ₃ HH Cl D-23-2c H 186.0-189.0
3-014 Cl CH ₃ HH Cl D-25-3a H 102.0-104.0
3-015 Cl CH ₃ OCH ₃ H Cl c-Pr H * 1
3-016 CHF ₂ CH ₃ OCH ₃ H Cl c-Pr H * 1
3-017 CF ₃ CH ₃ OCH ₃ H Cl c-Pr H * 1
3-018 Cl CH ₃ OCH ₃ H Cl Ph-4-FH * 1
3-019 CF ₃ CH ₃ OCH ₃ H Cl Ph-4-FH * 1
3-020 CF ₃ HFF Cl (D-23-2b) -6-FH 144.0-146.0
3-021 Cl CH ₃ HH Cl (D-6-3a) -1-CH ₃ H 75.0-77.0
3-022 CF ₃ CH ₃ HH Cl (D-6-3a) -1-CH ₃ H 106.0-108.0
3-023 CF ₃ CH ₃ FF Cl D-1-2a H * 1
3-024 Cl CH ₃ FF Cl (D-23-1b) -5-CF ₃ H * 1
3-025 CF ₃ CH ₃ FF Cl (D-23-2b) -6-CF ₃ H * 1
――――――――――――――――――――――――――――――――――――――――
Table 6

――――――――――――――――――――――――――――――――――――――――
No. X ¹ R ³ R ¹ R ² Y ¹ R ⁶ Y ² mp (℃)
――――――――――――――――――――――――――――――――――――――――
4-001 CF ₃ CH ₃ HH Cl c-Pr H 135.0-138.0
4-002 CF ₃ CH ₃ HH Cl c-Pr Cl 121.0-126.0
4-003 Cl CH ₃ HH Cl D-1-2a H 101.0-104.0
4-004 Cl CH ₃ HH Cl (D-6-2a) -1-CH ₃ H 142.0-146.0
4-005 Cl CH ₃ HH Cl D-23-2c H 168.0-171.0
4-006 Cl CH ₃ HH Cl D-25-3a H 171.0-173.0
4-007 CF ₃ CH ₃ OCH ₃ H Cl c-Pr H 115.0-116.0
4-008 Cl CH ₃ HH Cl (D-23-2b) -6-FH 118.0-120.0
――――――――――――――――――――――――――――――――――――――――
Table 7

――――――――――――――――――――――――――――――――――――――――
No. X ¹ R ³ R ¹ R ² Y ¹ R ⁶ Y ² mp (℃)
――――――――――――――――――――――――――――――――――――――――
5-001 CF ₃ CH ₃ HH Cl c-Pr Cl 172.0-174.0
5-002 CF ₃ CH ₃ OCH ₃ H Cl c-Pr H * 1
――――――――――――――――――――――――――――――――――――――――
Table 8

――――――――――――――――――――――――――――――――――――――――
No. R ³ R ¹ R ² Y ¹ R ⁶ Y ² mp (℃)
――――――――――――――――――――――――――――――――――――――――
6-001 CH ₃ HH Cl HH 67.0-70.0
6-002 CH ₃ HH Cl c-Pr H * 1
6-003 CH ₃ HH Cl c-Pr Cl 96.5-100.5
6-004 CH ₃ HH Cl Si (CH ₃ ) ₃ H 74.0-76.0
6-005 CH ₃ HH Cl D-1-2a H 58.0-59.0
6-006 CH ₃ HH Cl D-2-2a H 90.5-92.5
6-007 CH ₃ HH Cl (D-6-2a) -1-CH ₃ H 153.0-154.0
6-008 CH ₃ HH Cl (D-6-2b) -1-CH ₃ -3-CF ₃ H * 1
6-009 CH ₃ HH Cl (D-23-2b) -6-FH * 1
6-010 CH ₃ HH Cl D-23-2c H 158.0-159.0
6-011 CH ₃ HH Cl D-25-3a H 159.0-160.0
6-012 CH ₃ OCH ₃ H Cl c-Pr H * 1
6-013 CH ₃ OCH ₃ H Cl Ph-4-FH * 1
6-014 HFF Cl Si (CH ₃ ) ₃ H * 1
6-015 HFF Cl (D-23-1b) -5-CF ₃ H * 1
6-016 HFF Cl (D-23-2b) -6-FH * 1
6-017 HFF Cl (D-23-2b) -6-CF ₃ H * 1
6-018 CH ₃ HH Cl (D-6-3a) -1-CH ₃ H 90.0-62.0
6-019 CH ₃ FF Cl Si (CH ₃ ) ₃ H * 1
6-020 CH ₃ FF Cl D-1-2a H * 1
6-021 CH ₃ FF Cl (D-23-1b) -5-CF ₃ H * 1
6-022 CH ₃ FF Cl (D-23-2b) -6-CF ₃ H * 1
6-023 CH ₃ OCH ₃ H Cl Si (CH ₃ ) ₃ H * 1
――――――――――――――――――――――――――――――――――――――――
Table 9

――――――――――――――――――――――――――――――――――――――――
No. R ³ R ¹ R ² Y ¹ R ⁶ Y ² mp (℃)
――――――――――――――――――――――――――――――――――――――――
7-001 CH ₃ HH Cl c-Pr H * 1
7-002 CH ₃ HH Cl c-Pr Cl * 1
7-003 CH ₃ HH Cl D-1-2a H * 1
7-004 CH ₃ HH Cl D-2-2a H 142.0-145.0
7-005 CH ₃ HH Cl (D-6-2a) -1-CH ₃ H * 1
7-006 CH ₃ HH Cl (D-6-2b) -1-CH ₃ -3-CF ₃ H * 1
7-007 CH ₃ HH Cl (D-23-2b) -6-FH * 1
7-008 CH ₃ HH Cl D-23-2c H 165.0-167.0
7-009 CH ₃ HH Cl D-25-3a H * 1
7-010 CH ₃ OCH ₃ H Cl c-Pr H * 1
7-011 CH ₃ OCH ₃ H Cl Ph-4-FH * 1
7-012 HFF Cl (D-23-1b) -5-CF ₃ H * 1
7-013 HFF Cl (D-23-2b) -6-FH * 1
7-014 HFF Cl (D-23-2b) -6-CF ₃ H * 1
7-015 CH ₃ HH Cl (D-6-3a) -1-CH ₃ H * 1
7-016 CH ₃ FF Cl D-1-2a H * 1
7-017 CH ₃ FF Cl (D-23-1b) -5-CF ₃ H * 1
7-018 CH ₃ FF Cl (D-23-2b) -6-CF ₃ H * 1
――――――――――――――――――――――――――――――――――――――――
Table ¹ shows the ¹ H NMR data of the compounds in Tables 3 to 9 which do not have a melting point in the tables.
[Table 10]
――――――――――――――――――――――――――――――――――――――――
No. ¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz)
――――――――――――――――――――――――――――――――――――――――
1-003 δ7.45-7.75 (m, 3H), 7.35-7.45 (m, 1H), 7.2-7.35 (m, 3H),
6.22 and 6.02 (d, J = 9.0Hz, 1H), 4.75 and 4.62 (d, J = 3.6Hz, 1H),
4.4-4.65 (m, 1H), 3.28 and 3.27 (s, 3H), 1.4-1.5 (m, 1H),
1.38 and 1.04 (d, J = 6.9Hz, 3H), 0.75-0.95 (m, 4H).
1-004 δ7.6-7.75 (m, 2H), 7.4-7.6 (m, 4H), 7.2-7.35 (m, 3H), 7.05-7.1 (m, 2H),
6.1-6.3 and 5.9-6.1 (m, 1H), 4.7-4.8 and 4.55-4.7 (m, 1H),
4.4-4.55 (m, 1H), 3.29 and 3.28 (s, 3H),
1.41 and 1.40 (d, J = 6.8Hz, 3H).
1-009 δ8.8-8.9 (m, 1H), 7.95-8.05 (m, 1H), 7.65-7.75 (m, 2H),
7.6-7.65 (m, 2H), 7.45-7.55 (m, 3H), 7.25-7.35 (m, 1H),
5.88 (d, J = 9.5Hz, 1H), 5.3-5.55 (m, 1H), 1.35 (d, J = 7.1Hz, 3H).
2-007 δ8.7-8.8 (m, 1H), 8.05-8.2 (m, 1H), 7.84 (d, J = 9.3Hz, 1H),
7.5-7.6 (m, 1H), 7.35-7.4 (m, 1H), 7.25-7.35 (m, 1H),
7.19 and 7.16 (d, J = 1.2Hz, 1H), 4.78 and 4.72 (d, J = 3.6Hz, 1H),
4.5-4.65 and 4.35-4.5 (m, 1H), 3.33 and 3.31 (s, 3H), 1.4-1.5 (m, 1H),
1.39 and 1.10 (d, J = 6.9Hz, 3H), 0.75-0.95 (m, 4H).
2-011 δ8.75 (d, J = 4.4Hz, 1H), 8.53 (s, 1H), 8.17 (d, J = 7.2Hz, 1H),
7.95-8.1 (m, 1H), 7.55-7.65 (m, 1H), 7.45-7.55 (m, 2H),
7.3-7.35 (m, 1H), 7.07 (d, J = 7.2Hz, 1H), 6.65-6.85 (m, 1H),
4.32 (td, J = 14.3, 6.5Hz, 2H).
3-001 δ8.44 (dd, J = 4.8, 4.5Hz, 1H), 7.9-8.0 (m, 1H), 7.25-7.4 (m, 2H),
7.2-7.25 (m, 1H), 7.15-7.2 (m, 1H), 6.30 (bs, 1H), 4.45-4.65 (m, 1H),
2.9-3.15 (m, 2H), 1.35-1.5 (m, 1H), 1.33 (d, J = 6.3Hz, 3H),
0.85-0.9 (m, 2H), 0.7-0.8 (m, 2H).
3-003 δ8.74 (d, J = 4.8Hz, 1H), 7.65-7.75 (m, 1H), 7.45-7.55 (m, 1H),
7.3-7.4 (m, 1H), 7.15-7.25 (m, 2H), 5.71 (d, J = 8.1Hz, 1H),
4.4-4.65 (m, 1H), 2.85-3.15 (m, 2H), 1.35-1.55 (m, 1H),
1.30 (d, J = 6.6Hz, 3H), 0.85-0.95 (m, 2H), 0.75-0.85 (m, 2H).
3-009 δ8.44 (dd, J = 4.6, 1.8Hz, 1H), 7.8-8.1 (m, 1H), 7.59 (s, 1H),
7.48 (d, J = 1.5Hz, 1H), 7.25-7.4 (m, 3H), 6.36 (d, J = 8.3Hz, 1H),
4.45-4.65 (m, 1H), 3.95 (s, 3H), 2.95-3.15 (m, 2H),
1.33 (d, J = 6.7Hz, 3H).
3-015 δ8.45 and 8.43 (dd, J = 4.8, 2.1Hz, 1H),
8.12 and 8.09 (dd, J = 8.1, 2.1Hz, 1H), 7.2-7.45 (m, 4H),
6.94 and 6.73 (d, J = 9.0Hz, 1H), 4.77 and 4.65 (d, J = 3.9Hz, 1H),
4.4-4.65 (m, 1H), 3.32 (s, 3H), 1.4-1.5 (m, 1H),
1.39 and 1.07 (d, J = 6.9Hz, 3H), 0.75-0.95 (m, 4H).
3-016 δ8.7-8.75 (m, 1H), 7.9-8.0 and 7.7-7.75 (m, 1H), 7.4-7.55 (m, 2H),
7.2-7.4 (m, 2H), 6.94 and 6.81 (t, J = 54.3Hz, 1H),
6.49 and 6.23 (d, J = 8.1Hz, 1H), 4.75 and 4.63 (d, J = 3.6Hz, 1H),
4.4-4.6 (m, 1H), 3.30 and 3.29 (s, 3H), 1.4-1.5 (m, 1H),
1.40 and 1.07 (d, J = 7.2Hz, 3H), 0.75-1.0 (m, 4H).
3-018 δ8.45-8.5 and 8.4-8.45 (m, 1H), 8.1-8.15 and 7.9-7.95 (m, 1H),
7.45-7.6 (m, 3H), 7.25-7.4 (m, 3H), 7.0-7.15 (m, 2H),
6.85-7.0 and 6.7-6.8 (m, 1H), 4.75-4.85 and 4.6-4.7 (m, 1H),
4.45-4.6 (m, 1H), 3.33 and 3.32 (s, 3H),
1.45 and 1.43 (d, J = 7.5Hz, 3H).
3-019 δ8.7-8.8 (m, 1H), 7.85-7.95 (m, 1H), 7.45-7.7 (m, 3H),
7.35-7.45 (m, 2H), 7.25-7.35 (m, 1H), 7.15-7.25 (m, 1H),
7.0-7.1 (m, 1H), 6.2-6.35 and 6.0-6.15 (m, 1H),
4.7-4.8 and 4.55-4.7 (m, 1H), 4.4-4.55 (m, 1H), 3.30 and 3.29 (s, 3H),
1.43 and 1.41 (d, J = 7.2Hz, 3H).
3-023 δ8.76 (dd, J = 4.8, 1.8Hz, 1H), 7.73 (dd, J = 1.5, 0.6Hz, 1H),
7.70 (dd, J = 8.1, 0.9Hz, 1H), 7.61 (d, J = 0.9Hz, 1H), 7.5-7.55 (m, 2H),
7.4-7.45 (m, 2H), 6.53 (dd, J = 1.8, 0.6Hz, 1H), 5.95 (d, J = 9.6Hz, 1H),
5.3-5.5 (m, 1H), 1.34 (d, J = 6.6Hz, 3H).
3-024 δ8.89 (s, 1H), 8.4-8.5 (m, 1H), 7.9-8.0 (m, 2H), 7.72 (s, 1H),
7.4-7.7 (m, 2H), 7.3-7.4 (m, 2H), 6.61 (d, J = 9.6Hz, 1H),
5.3-5.6 (m, 1H), 1.41 (d, J = 6.8Hz, 3H).
3-025 δ8.8-8.85 (m, 1H), 8.7-8.75 (m, 1H), 7.95-8.25 (m, 1H),
7.65-7.75 (m, 3H), 7.55-7.6 (m, 1H), 7.5-7.55 (m, 2H),
5.9-6.05 (m, 1H), 5.35-5.55 (m, 1H), 1.34 (d, J = 6.7Hz, 3H).
5-002 δ7.35-7.4 (m, 1H), 7.25-7.3 (m, 2H), 6.18 and 6.07 (d, J = 9.0Hz, 1H),
4.65 and 4.56 (d, J = 3.6Hz, 1H), 4.15-4.5 (m, 3H),
3.29 and 3.28 (s, 3H), 3.05-3.15 (m, 2H), 1.35-1.5 (m, 1H),
1.31 and 0.96 (d, J = 6.9Hz, 3H), 0.85-0.95 (m, 2H), 0.75-0.85 (m, 2H).
6-008 δ7.58 (s, 1H), 7.46 (d, J = 1.5Hz, 1H), 7.25-7.35 (m, 1H),
7.15-7.25 (m, 1H), 4.42 (bs, 1H), 3.9-4.05 (m, 4H),
2.88 (d, J = 6.4Hz, 2H), 1.37 (s, 9H), 1.15 (d, J = 6.4Hz, 3H).
6-013 δ7.35-7.65 (m, 3H), 7.15-7.35 (m, 2H), 7.0-7.1 (m, 2H),
4.8-4.95 (m, 1H), 4.45-4.75 (m, 1H), 3.9-4.05 (m, 1H),
3.27 and 3.26 (s, 3H), 1.43 and 1.41 (s, 9H), 0.98 (d, J = 6.8Hz, 3H).
6-015 δ8.75-8.95 (m, 1H), 7.85-8.05 (m, 1H), 7.55-7.8 (m, 1H),
7.3-7.55 (m, 3H), 4.7-4.9 (m, 1H), 3.96 (td, J = 14.4, 6.4Hz, 2H),
1.35 (s, 9H).
6-017 δ8.54 (s, 1H), 7.6-7.9 (m, 2H), 7.3-7.55 (m, 2H), 6.6-6.85 (m, 1H),
4.75-4.95 (m, 1H), 3.8-4.05 (m, 2H), 1.35 (s, 9H).
6-020 δ7.71 (s, 1H), 7.55 (s, 1H), 7.50 (d, J = 8.1Hz, 1H),
7.42 (dd, J = 1.8, 1.5Hz, 1H), 7.38 (d, J = 8.1Hz, 1H),
6.52 (d, J = 1.5Hz, 1H), 4.75-4.8 (m, 1H), 4.62 (d, J = 10.2Hz, 1H),
1.29 (s, 9H), 1.27 (d, J = 6.6Hz, 3H).
6-021 δ8.88 (s, 1H), 7.9-8.0 (m, 1H), 7.75-7.85 (m, 1H), 7.6-7.7 (m, 2H),
7.3-7.55 (m, 1H), 4.7-4.9 (m, 1H), 4.5-4.6 (m, 1H), 1.25-1.3 (m, 12H).
6-023 δ7.4-7.5 (m, 1H), 7.3-7.4 (m, 3H), 4.6-4.65 and 4.5-4.55 (m, 1H),
3.9-4.05 (m, 1H), 3.26 and 3.25 (s, 3H), 1.54 and 1.42 (s, 9H),
0.9-1.0 and 0.8-0.9 (m, 3H), 0.24 and 0.23 (s, 9H).
7-002 δ7.30 (s, 2H), 3.25-3.4 (m, 1H), 2.9-3.0 (m, 1H), 1.3-1.5 (m, 1H),
1.15 (d, J = 6.3Hz, 3H), 0.75-0.95 (m, 4H).
7-005 δ7.65 (s, 1H), 7.55 (s, 1H), 7.50 (s, 1H), 7.2-7.35 (m, 2H),
3.92 (s, 3H), 3.6-3.75 (m, 1H), 2.9-3.25 (m, 2H), 1.86 (bs, 2H),
1.3-1.4 (m, 3H).
7-006 δ7.59 (s, 1H), 7.4-7.55 (m, 1H), 7.25-7.35 (m, 1H),
7.19 (d, J = 7.7Hz, 1H), 3.95 (s, 3H), 3.1-3.5 (m, 1H),
2.84 (dd, J = 13.2, 5.8Hz, 1H), 2.70 (dd, J = 13.2, 5.8Hz, 1H),
1.56 (bs, 2H), 1.14 (d, J = 6.1Hz, 3H).
7-009 δ9.15 (s, 1H), 8.84 (s, 2H), 7.57 (d, J = 1.4Hz, 1H),
7.39 (dd, J = 7.8, 1.4Hz, 1H), 7.25-7.3 (m, 1H), 2.7-3.05 (m, 3H),
1.15-1.25 (m, 3H).
7-011 δ7.4-7.6 (m, 3H), 7.2-7.4 (m, 3H), 6.95-7.1 (m, 1H),
4.45-4.6 and 4.3-4.45 (m, 1H), 3.25 and 3.21 (s, 3H), 2.95-3.2 (m, 1H),
1.71 (bs, 2H), 1.01 and 1.00 (d, J = 7.1Hz, 3H).
7-012 δ8.75-8.9 (m, 1H), 7.85-7.95 (m, 1H), 7.55-7.75 (m, 1H),
7.3-7.55 (m, 3H), 3.15-3.55 (m, 2H), 1.2-1.5 (bs, 2H).
7-014 δ8.55 (s, 1H), 7.35-7.85 (m, 4H), 6.55-6.9 (m, 1H), 3.3-3.5 (m, 2H),
1.29 (bs, 2H).
7-015 δ7.54 (d, J = 1.4Hz, 1H), 7.47 (d, J = 2.1Hz, 1H), 7.3-7.4 (m, 1H),
7.2-7.25 (m, 1H), 6.48 (d, J = 2.1Hz, 1H), 3.98 (s, 3H),
3.25-3.5 (m, 1H), 2.75-3.0 (m, 2H), 1.15-1.3 (m, 3H).
7-016 δ7.72 (dd, J = 1.5, 0.9Hz, 1H), 7.57 (s, 1H), 7.54 (d, J = 8.7Hz, 1H),
7.43 (dd, J = 1.8, 1.5Hz, 1H), 7.42 (d, J = 8.7Hz, 1H),
6.53 (dd, J = 1.8, 0.9Hz, 1H), 3.7-3.85 (m, 1H), 1.53 (bs, 2H),
1.11 (d, J = 6.6Hz, 3H).
7-017 δ8.88 (s, 1H), 7.9-8.0 (m, 1H), 7.5-7.7 (m, 2H), 7.3-7.45 (m, 2H),
3.7-3.9 (m, 1H), 1.3-1.5 (bs, 2H), 1.05-1.15 (m, 3H).
――――――――――――――――――――――――――――――――――――――――
(Test example)
Next, the usefulness of the compound of the present invention as a pesticidal agent will be specifically described in the following test examples, but the present invention is not limited thereto.

  Preparation of test drug solution A; emulsified white sample of the compound of the present invention (Solpol (registered trademark) 3005XL (manufactured by Toho Chemical Industry): N-methylpyrrolidone: Solvesso (registered trademark) 200 (manufactured by ExxonMobil) = 1: 5: 2 mixture ) To prepare a 20% concentration emulsion. This drug solution was diluted to a predetermined concentration and tested in 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% concentration solution. This drug solution was diluted to a predetermined concentration and tested in the following Test Examples 9 to 13.

Test Example 1 Cucumber Powdery Mildew Preventive Effect Test Cucumber (cultivar: Sagami Hanjiro) was planted in a 90 cm ³ plastic pot, and a test drug solution A of the compound of the present invention was diluted to 500 ppm concentration by adding distilled water to the cotyledon stage. 5 ml was sprayed per pot. After air drying, the cucumber was placed in an air-conditioned greenhouse (20 ° C.) and sprayed with a conidia suspension of cucumber powdery mildew (Erysiphe polygoni, Synonym; Erysiphe betae). After being left at the same temperature for 9 days, the ratio of the formed lesions to the inoculated leaves was measured, and the control value was calculated according to the following formula. Note that the test was performed in a two-part system.

Control value = [1- (area ratio of treated spot / area ratio of untreated section)] × 100
As a result, among the tested compounds, the following compounds showed a control value of 70% or more.
Compound of the present invention: No. 1-002, 1-003, 1-004, 2-001, 2-007, 2-012, 3-001, 3-002, 3-003, 3-007, 3-011, 3-015,3-016,3-017,3-018,3-019,3-022,4-001,4-002 ^* , 4-007,5-002.

Note that the asterisk ^* indicates that the test was performed using a 100 ppm concentration drug solution.

Test Example 2 Cucumber Gray Mold Prevention Effect Test (Spore Inoculation)
Cucumber (cultivar: Sagami Hanjiro) was planted in a 90 cm ³ plastic pot, and the test drug solution A of the compound of the present invention was diluted with distilled water to a concentration of 500 ppm at the cotyledon stage, and sprayed 5 ml per pot. After air drying, the treated leaves were cut off and placed in a plastic container. A conidial suspension of cucumber gray mold fungus (Botrytis cinerea) and a dissolved PDA medium were mixed at a ratio of 1: 1 and 30 μl of the treated leaves were instilled in drops. After inoculation, the inoculated leaves were kept at 20 ° C. and in a humid condition for 3 days, and 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. Note that the test was performed in a two-part system.

As a result, among the tested compounds, the following compounds showed a control value of 70% or more.
Compound of the present invention: No. 1-001, 1-002, 1-003, 1-004, 1-008, 2-001, 2-002, 2-003, 2-004, 2-005, 2-007, 2-010,2-012,2-013,2-014,3-001,3-002,3-003,3-005,3-006,3-007,3-009,3-010,3- 011,3-012,3-013,3-014,3-015,3-016,3-017,3-018,3-019,3-020,3-021,3-022,3-024, 4-001,4-002 ^* , 4-003,4-004,4-005,4-006,4-007,4-008 ^* , 5-002.

Note that the asterisk ^* indicates that the test was performed using a 100 ppm concentration drug solution.

Test Example 3 Cucumber gray mold preventive effect test (hyphae inoculation)
Cucumber (cultivar: Sagami Hanjiro) was planted in a 90 cm ³ plastic pot, and the test drug solution A of the compound of the present invention was diluted with distilled water to a concentration of 500 ppm at the cotyledon stage, and sprayed 5 ml per pot. One day later, the pot was placed in a plastic container, and agar-containing agar pieces (diameter: 5 mm) of cucumber Botrytis cinerea, which had been cultured in a PDA medium in advance, were inoculated to the cucumber cotyledons treated with the drug. After inoculation, the plastic container was covered with vinyl and humidified, left at 20 ° C. for 2 days, and 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. did. Note that the test was performed in a two-part system.

As a result, among the tested compounds, the following compounds showed a control value of 70% or more.
Compound of the present invention: No. 1-001, 1-004, 2-001, 2-003, 2-004, 2-007, 2-014, 3-001, 3-002, 3-003, 3-005, 3-006,3-009,3-010,3-011,3-012,3-015,3-016,3-017,3-018,3-019,3-024,4-001,4- 002 ^* , 4-003,4-004,4-005,4-006,4-007,5-002.

Note that the asterisk ^* indicates that the test was performed using a 100 ppm concentration drug solution.

Test Example 4 Test for Preventive Effect of Cucumber Sclerotium Cucumber (cultivar: Sagami Hanjiro) was planted in a 90 cm ³ plastic pot, and the test drug solution A of the compound of the present invention was diluted with distilled water to a concentration of 500 ppm in the cotyledon stage. 5 ml was sprayed per pot. After air-drying, the pot was put in a plastic container, and agar-containing agar pieces (5 mm in diameter) of cucumber sclerotinia (Sclerotinia sclerotiorum) previously cultured in a PDA medium were inoculated to the cotyledons of the cucumber treated with the drug. After inoculation, the plastic container was covered with vinyl and humidified, left at 20 ° C. for 2 days, and 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. did. Note that the test was performed in a two-part system.

As a result, among the tested compounds, the following compounds showed a control value of 70% or more.
Compound of the present invention: No. 1-001, 1-003, 1-004, 1-008, 2-001, 2-002, 2-003, 2-004, 2-005, 2-007, 2-009, 2-010,2-012,2-013,2-014,3-001,3-002,3-003,3-004,3-005,3-006,3-007,3-009,3- 010,3-011,3-012,3-013,3-014,3-015,3-016,3-017,3-018,3-019,3-020,3-021,3-022, 3-024,4-001,4-002 ^* , 4-003,4-004,4-005,4-006,4-007,4-008 ^* , 5-002.

Note that the asterisk ^* indicates that the test was performed using a 100 ppm concentration drug solution.

Test Example 5 Cucumber Anthrax Disease Preventive Effect Test Cucumber (cultivar: Sagami Hanjiro) 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 500 ppm concentration with distilled water at the cotyledon stage. 5 ml per spraying. One day later, a conidia spore suspension of cucumber anthrax (Colletotrichum lagenarium, Synonym; Colletotrichum orbiculare) was spray-inoculated and placed in an inoculation box at 25 ° C and 100% humidity for 2 days. After that, it was placed in an air-conditioned greenhouse (23 ° C.) and kept at the same temperature for 7 days. Then, 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. . Note that the test was performed in a two-part system.

As a result, among the tested compounds, the following compounds showed a control value of 70% or more.
Compound of the present invention: No. 1-002, 2-001, 3-003, 3-004, 3-006, 3-007, 3-009, 3-011, 3-017, 3-018, 3-019, 3-021,3-022,4-002 ^* , 4-004.

Note that the asterisk ^* indicates that the test was performed using a 100 ppm concentration drug solution.

Test Example 6 Wheat Powdery Mildew Prevention Effect Test A test drug solution A of the compound of the present invention was added to a 90 cm ³ plastic pot planted with 1.3-leaf wheat (cultivar: Norin 61) by adding distilled water to a concentration of 500 ppm. And sprayed 5 ml per pot. One day after spraying, the pot was placed in an air-conditioned greenhouse (20 ° C.) and wheat was inoculated with conidiospores of wheat powdery mildew (Blumeria graminis f. Sp. Tritici). After that, the cells were kept 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. Note that the test was performed in a two-part system.

As a result, among the tested compounds, the following compounds showed a control value of 70% or more.
Compound of the present invention: No. 1-001, 1-003, 1-004, 1-008, 2-001, 2-003, 2-004, 2-007, 2-010, 2-012, 2-013, 2-014,3-001,3-002,3-003,3-004,3-005,3-006,3-009,3-010,3-011,3-015,3-016,3- 017,3-018,3-019,3-021,3-022,3-024,4-001,4-002 ^* , 4-003,4-004,4-007,4-008 ^* , 5- 002.

Note that the asterisk ^* indicates that the test was performed using a 100 ppm concentration drug solution.

Test Example 7 Wheat Blight Preventive Effect Test 1.3 Test leaf A of the compound of the present invention was diluted with distilled water to a concentration of 500 ppm in a 90 cm ³ plastic pot planted with 1.3-leaf wheat (cultivar: Harutaka). And sprayed 5 ml per pot. One day after spraying, a conidia 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. Then, it was placed in an air-conditioned greenhouse (20 ° C.) and kept for 6 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. Note that the test was performed in a two-part system.

As a result, among the tested compounds, the following compounds showed a control value of 70% or more.
Compound of the present invention: No. 1-002, 1-003, 1-004, 2-001, 2-007, 3-001, 3-002, 3-004, 3-005, 3-011, 3-012, 3-016,3-017,3-018,3-019,4-001,4-002 ^* , 4-003,4-005,4-007,5-001 ^* , 5-002.

Note that the asterisk ^* indicates that the test was performed using a 100 ppm concentration drug solution.

Test Example 8 Wheat Leaf Rust Preventive Effect Test A test drug solution A of the compound of the present invention was added to a 90 cm ³ plastic pot planted with 1.3-leaf wheat (variety: Norin 61) to a concentration of 500 ppm by adding distilled water. Diluted and sprayed 5 ml per pot. One day after spraying, a spore suspension of wheat leaf rust (Puccinia recondita) was spray-inoculated on wheat and placed in an inoculation box at a temperature of 20 ° C and a humidity of 100% for 1 day. Then, it was placed in an air-conditioned greenhouse (20 ° C.) and kept for 8 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. Note that the test was performed in a two-part system.

As a result, among the tested compounds, the following compounds showed a control value of 70% or more.
Compound of the present invention: No. 3-022, 4-002 ^* .

Note that the asterisk ^* indicates that the test was performed using a 100 ppm concentration drug solution.

Test Example 9 Antibacterial activity test against black mold fungus Potato dextrose 1% agar medium was dispensed into a 96-well plate in an amount of 60 μl each, and sterilized water containing spores of black mold fungus (Aspergillus niger) (10 spores / 3 μl) was added. , 30 μl per well. From above, the test drug solution B of the compound of the present invention was diluted with distilled water to a concentration of 100 ppm, added at 10 μl / well, and allowed to stand at 25 ° C. under dark conditions. The area ratio (%) of the bacterial flora two days after the addition of the drug was determined, and the efficiency (%) for the untreated group was calculated by the following formula.

efficacy (%) = [1- (area ratio of treated flora / area ratio of untreated group flora)] × 100
As a result, of the compounds tested, the following compounds showed 50% or more efficacy (%).
Compound of the present invention: No. 1-001, 1-002, 1-003, 1-004, 1-008, 1-009, 2-001, 2-002, 2-003, 2-004, 2-005, 2-006,2-007,2-012,2-013,2-014,2-015,3-001,3-002,3-003,3-004,3-005,3-006,3- 007,3-008,3-009,3-010,3-011,3-012,3-013,3-015,3-016,3-017,3-018,3-019,3-020, 3-021,3-022,3-024,3-025,4-001,4-003,4-004,4-005,4-006,4-007,4-008,5-002.

Test Example 10 Insecticidal test against sweet potato nematode After potato dextrose 1% agar medium was dispensed into a 96-well plate by 60 μl each, sterile water (10 eggs / 3 μl) containing eggs of sweet potato nematode (Meloidogyne incognita) was added to each well. 30 μl was added per each. From above, the test drug solution B of the compound of the present invention was diluted to 100 ppm concentration by adding distilled water, diluted to 10 ppm concentration by adding distilled water, and added at 10 μl per well, and the temperature was adjusted to 25 ° C. under dark conditions. And left still. 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 plot was calculated by the following formula.

efficacy (%) = [(number of unhatched eggs in treated area + number of inactive larvae) / number of active larvae in untreated area] x 100
As a result, of the compounds tested, the following compounds showed 50% or more efficacy (%).
Compound of the present invention: No. 1-001, 1-004, 1-009, 2-003, 2-004, 2-007, 2-009, 2-010, 2-012, 2-013, 2-014, 2-015,3-001,3-002,3-003,3-004,3-005,3-006,3-007,3-008,3-010,3-011,3-013,3- 015,3-016,3-017,3-018,3-019,3-020,3-021,3-022,3-024,3-025,4-001,4-003,4-007.

Test Example 11 Test of Control Effect on Sweet Potato Nematode Necroticum A test drug solution B of the compound of the present invention was added to a stock root of a cell tray planted with a cell tray plant filled with 10 g of soil per cell (about 2 weeks after germination) by adding distilled water to 100 ppm. It was diluted to a concentration and treated at 1 ml per strain. One hour after the treatment, the strain was inoculated with 1 L of water containing 2 L larvae of the root-knot nematode (Meloidogyne incognita) at a rate of 1 ml per cell. It was kept in a greenhouse for 3 weeks, the degree of epiphytic formation of the galls formed on the root was determined according to the following disease index and disease severity, and the efficiency (%) for the untreated plot was calculated by the following formula.

  <Disease index> 0: No bump is observed. 1: A hump is recognized in a part of the root system.

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

              4: Large nodules are observed throughout the root system.

[Degree of disease] = [Σ (Disease index × Number of diseased strains by index) / (4 × Number of investigated strains)] × 100
efficacy (%) = [1- (development degree of treated area / degree of untreated area)] × 100
As a result, of the compounds tested, the following compounds showed 50% or more efficacy (%).
Compound of the present invention: No. 2-007, 3-001, 3-003, 3-004, 3-005, 3-015, 3-016, 4-001, 4-007.

Test Example 12 Insecticidal test against Tortoise worms After dispensing 60 μl of potato dextrose 1% agar medium into a 96-well plate, sterilized water (10 eggs / 3 μl) containing eggs of Tortoise worms (Haemonchus contortus) was added. 30 μl was added per well. From above, the test drug solution B of the compound of the present invention was diluted with distilled water to a concentration of 100 ppm, added at 10 μl / 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 plot was calculated from the same formula as in Test Example 9.

As a result, of the compounds tested, the following compounds showed 50% or more efficacy (%).
Compound of the present invention: No. 1-001, 1-002, 1-003, 1-004, 1-005, 1-006, 1-008, 1-009, 2-001, 2-002, 2-003, 2-004,2-005,2-006,2-007,2-008,2-009,2-010,2-011,2-012,2-013,2-014,2-015,3- 001,3-002,3-003,3-004,3-005,3-006,3-007,3-008,3-009,3-010,3-011,3-012,3-013, 3-014,3-015,3-016,3-017,3-018,3-019,3-020,3-021,3-022,3-024,3-025,4-001,4- 003,4-004,4-005,4-006,4-007,4-008,5-002.

Test Example 13 Insecticidal test against soybean cyst nematode After dispensing 60 μl of potato dextrose 1% agar medium into a 96-well plate, sterilized water containing 2 L larvae of callus-cultured soybean cyst nematode (Heterodera glycines) (10 larvae / 3 μl) was added at 30 μl per well. From above, the test drug solution B of the compound of the present invention was diluted with distilled water to a concentration of 100 ppm, added at 10 μl / well, and allowed to stand at 25 ° C. under dark conditions. The number of inactive larvae 4 days after the addition of the drug was counted, and the efficiency (%) with respect to the untreated plot was calculated by the following formula.

efficacy (%) = (number of inactive larvae in treated area / number of active larvae in untreated area) × 100
As a result, of the compounds tested, the following compounds showed 50% or more efficacy (%).
Compound of the present invention: No. 1-009, 2-010, 2-014, 2-015, 3-024, 3-025.

  The alkynylphenyl-substituted amide compound according to the present invention exhibits excellent pest control activity, particularly fungicidal and nematicidal activities, and has almost no adverse effect on non-target organisms such as mammals, fish and useful insects. Is a very useful compound.

Claims (22)

An alkynylpyridine-substituted amide compound represented by the formula (I), an N-oxide or a salt thereof.

Wherein, G ¹ represents a structure represented by G ¹ -1~G ¹ -7,

X ¹ is a halogen atom, cyano, nitro, C ₁ -C ₄ alkyl, C ₁ -C ₃ haloalkyl, C ₁ -C ₃ alkoxy, C ₁ -C ₃ haloalkoxy, C ₁ -C ₃ alkylthio, C ₁ -C ₃ C ₃ alkylsulfinyl, C ₁ -C ₃ alkylsulfonyl, C ₁ -C ₃ represents a haloalkylthio or _C 1 -C ₃ haloalkylsulfonyl,
X ² represents a hydrogen atom or a halogen atom,
Y ¹ represents a hydrogen atom, a halogen atom, nitro, C ₁ -C ₄ alkyl, C ₁ -C ₃ haloalkyl, C ₁ -C ₃ alkoxy, C ₁ -C ₃ haloalkoxy or C ₁ -C ₃ alkylthio,
Y ² represents a hydrogen atom, a halogen atom, cyano or methyl,
R ¹ represents a hydrogen atom, a halogen atom, cyano, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, phenyl _(C 1 _{~C 4)} alkyl, _(Z) phenyl substituted by _{m (C} 1 -C ₄₎ alkyl, C ₃ -C ₆ cycloalkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, C ₃ -C ₆ alkenyloxy, C ₃ -C ₆ haloalkenyloxy, C ₃ -C ₆ alkynyloxy, C ₃ -C ₆ haloalkynyloxy, cyano _(C 1 ~C ₄₎ alkoxy, phenyl _(C 1 ~C ₄₎ alkoxy, by _{(Z) m} substituted phenyl _(C 1 _{~C 4)} alkoxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ haloalkylthio, C ₁ -C ₆ alkoxy amino, -C (O) NH ₂ or -C (S) NH ₂
R ² represents a hydrogen atom, a halogen atom or C ₁ -C ₆ alkyl,
Alternatively, R ¹ and R ² together form a C ₂ -C ₅ alkylene chain to form a 3- to 6-membered ring together with the carbon atom to which R ¹ and R ² are attached. chain represents the oxygen atom, may contain one to two sulfur atom or a nitrogen atom, and C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, may be optionally substituted by oxo or thioxo,
R ³ represents a hydrogen atom, C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
R ⁴ represents 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 attached;
R ⁵ is a hydrogen atom, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, (C ₁ -C ₂ ) alkyl substituted by R ⁷ , C ₃ -C ₆ cycloalkyl, C ₂ -C ₄ alkenyl , C ₃ -C ₄ alkynyl, -OH, C ₁ ~C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ haloalkylthio, -C a (O) ^{R 8} or _C 1 -C ₄ alkoxycarbonyl Represent
R ⁶ is a hydrogen atom, a halogen atom, a C ₁ -C ₆ alkyl, a C ₁ -C ₆ haloalkyl, a (C ₁ -C ₄ ) alkyl optionally substituted with R ⁹ , a C ₃ -C ₁₀ cycloalkyl, ₃ -C ₁₀ halocycloalkyl, C ₃ -C ₆ cycloalkyl _(C 3 ~C ₆₎ cycloalkyl, hydroxy _(C 3 ~C ₆₎ cycloalkyl, C ₁ -C ₂ alkoxy _(C 3 ~C ₆₎ cycloalkyl alkyl, phenyl _(C 3 -C ₆₎ cycloalkyl, C ₄ -C ₁₀ cycloalkenyl, C ₄ -C ₁₀ halo cycloalkenyl, tri _(C 1 -C ₄ alkyl) silyl, phenyl dimethylsilyl, -C ^{(R 10} ) = NOR ¹¹ , phenyl, phenyl substituted by (Z) _m or D-1 to D-29,
D-1 to D-29 each represent an aromatic heterocyclic ring represented by the following structural formula,

Z is a halogen atom, cyano, nitro, -SF _5, C ₁ ~C ₄ alkyl, C ₁ -C ₄ haloalkyl, cyano _(C 1 _{~C 4)} alkyl, C ₁ -C ₄ alkoxy _(C 1 -C ₄ ) Alkyl, C ₁ -C ₄ haloalkoxy (C ₁ -C ₄ ) alkyl, C ₁ -C ₄ alkylthio (C ₁ -C ₄ ) alkyl, C ₁ -C ₄ alkylsulfinyl (C ₁ -C ₄ ) alkyl, C ₁ -C ₄ alkylsulfonyl _(C 1 _{~C 4)} alkyl, C ₁ -C ₄ haloalkylthio _(C 1 _{~C 4)} alkyl, C ₁ -C ₄ haloalkylsulfinyl _(C 1 _{~C 4)} alkyl, C ₁ -C ₄ haloalkylsulfonyl _(C 1 ~C ₄₎ alkyl, C ₃ -C ₄ cycloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkyl sulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ Haroaru In the case where m represents 1 or more, and m or n represents 2 or more, represents thiothio, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ haloalkylsulfonyl, di (C ₁ -C ₄ alkyl) amino, phenyl or D-30 to D-38. the, each Z is independently selected from groups or different from each other be identical to each other, further, when two Z are adjacent, the two adjacent Z is -CH ₂ CH ₂ CH 2 _-, - CH ₂ CH ₂ O—, —CH ₂ OCH ₂ —, —OCH ₂ O—, —CH ₂ CH ₂ S (O) _r —, —CH ₂ S (O) _r CH ₂ —, —SCH ₂ S—, -CH ₂ CH ₂ CH ₂ CH _2- , -CH ₂ CH ₂ CH ₂ O-, -CH ₂ CH ₂ OCH _2- , -CH ₂ OCH ₂ O-, -OCH ₂ CH ₂ O-, -CH ₂ CH ₂ CH ₂ S (O) _r- , -CH ₂ CH ₂ S (O) _r CH _2- , -OCH ₂ CH ₂ S-, -SCH ₂ CH ₂ S-, -OCH = CH-, -SCH = CH _{-, - SO 2 CH = CH} -, - N (R 12) CH = CH -, - OCH = N -, - SCH = N -, - N (R 12) CH = N -, - ON = CH-, _{-SN = CH -, - SO 2} N = CH -, - N (R 12) N = CH -, - ON = N -, - SN = N -, - N (R 12) N = N- = NOCH =, = NSCH =, = = NN (R 12) CH, = NON =, = NSN =, = NN (R 12) N =, - CH = CHCH = CH -, - N = CHCH = CH-, -CH = NCH = CH-, -N = NCH = CH-, -N = CHN = CH-, -N = CHCH = N-, -CH = NN = CH- or -N = NCH = N- Thus, a 5- or 6-membered ring may be formed together with the carbon atom to which each Z is bonded, wherein the hydrogen atom bonded to each carbon atom forming the ring is a halogen atom, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, may be optionally substituted by C ₁ -C ₄ haloalkoxy or _C 1 -C ₄ haloalkylthio,
D-30 to D-38 each represent an aromatic heterocycle represented by the following structural formula,

Z ^a is a halogen atom, cyano, methyl, difluoromethyl, trifluoromethyl, cyclopropyl, methoxy or trifluoromethylsulfonyl, in the case where n is 2 or more, each Z ^a are the same to each other Or may be different from each other,
R ⁷ is cyano, C ₃ -C ₆ cycloalkyl, —OR ¹³ , C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkoxycarbonyl, —C (O) NH ₂ , —C (S) NH ₂ , phenyl , (Z) represents phenyl or D-23 substituted by _m ,
R ⁸ represents C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxymethyl, C ₃ -C ₄ cycloalkyl or C ₂ -C ₄ alkenyl,
R ⁹ represents cyano, —OR ¹⁴ , —S (O) _r R ¹⁵ or —N (R ¹⁷ ) R ¹⁶ ;
R ¹⁰ represents a hydrogen atom or C ₁ -C ₄ alkyl,
R ¹¹ represents C ₁ -C ₄ alkyl,
R ¹² is a hydrogen atom, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₃ -C ₄ cycloalkylmethyl, C ₃ -C ₄ halocycloalkylmethyl, C ₃ -C ₄ cycloalkyl or C ₃ -C ₄ represents halo cycloalkyl,
R ¹³ represents C ₁ -C ₄ alkyl, C ₂ -C ₄ haloalkyl, C ₁ -C ₄ alkylcarbonyl, C ₃ -C ₆ cycloalkylcarbonyl or C ₁ -C ₄ alkoxycarbonyl,
R ¹⁴ is a hydrogen atom, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy (C ₁ -C ₂ ) alkyl, E-1, E-2, C ₃ -C ₄ alkenyl , C ₃ -C ₄ represents haloalkenyl, C ₃ -C ₄ alkynyl, C ₃ -C ₄ haloalkynyl, phenyl substituted by phenyl or _{(Z) m,}
E-1 and E-2 each represent a saturated heterocyclic ring represented by the following structural formula,

R ¹⁵ is C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy (C ₁ -C ₂ ) alkyl, C ₃ -C ₄ alkenyl, C ₃ -C ₄ haloalkenyl, C ₃ -C ₄ represents alkynyl, C ₃ -C ₄ haloalkynyl, phenyl substituted by phenyl or _{(Z) m,}
R ¹⁶ and R ¹⁷ are each independently a hydrogen atom, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy (C ₁ -C ₂ ) alkyl, C ₃ -C ₄ alkenyl, Stands for C ₃ -C ₄ alkynyl, phenyl or phenyl substituted by (Z) _m ,
Alternatively, R ¹⁶ and R ¹⁷ may together form a C ₂ -C ₅ alkylene chain to form a 3- to 6-membered ring with the nitrogen atom to which R ¹⁶ and R ¹⁷ are attached. Wherein the alkylene chain may contain one oxygen atom or sulfur atom, and may be optionally substituted by C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, oxo or thioxo,
R ¹⁸ represents C ₁ -C ₄ alkyl, and when p represents 2, each R ¹⁸ may be the same as or different from each other;
m represents 1, 2, 3, 4 or 5;
n represents 0, 1, 2, 3, or 4;
p represents 0, 1 or 2;
r represents 0, 1 or 2. ] X ¹ represents a halogen atom, nitro, methyl, difluoromethyl, trifluoromethyl, methylsulfonyl, difluoromethylsulfonyl or trifluoromethylsulfonyl,
X ² represents a hydrogen atom, a fluorine atom or a chlorine atom,
Y ¹ represents a halogen atom, methyl or methoxy,
Y ² represents a hydrogen atom, a fluorine atom, a chlorine atom or methyl,
R ¹ is a hydrogen atom, a fluorine atom, a C ₁ -C ₃ alkyl, a C ₁ -C ₃ haloalkyl, a benzyl, a phenylmethyl, a cyclopropyl, a C ₁ -C ₃ alkoxy, a C ₁ -C ₃ substituted by (Z) _m . C ₃ haloalkoxy, C ₃ -C ₄ alkenyloxy, C ₃ -C ₄ alkynyloxy, cyano, methoxy, benzyloxy, _(Z) phenylmethoxy substituted by _m, C ₁ -C ₃ alkylthio or _C 1 -C ₃ Represents haloalkylthio,
R ² represents a hydrogen atom, a fluorine atom or C ₁ -C ₃ alkyl,
Alternatively, R ¹ and R ² together form an ethylene chain, thereby forming a cyclopropyl ring together with the carbon atom to which R ¹ and R ² are attached;
R ³ represents a hydrogen atom, C ₁ -C ₃ alkyl or C ₁ -C ₃ haloalkyl,
R ⁴ represents a hydrogen atom or C ₁ -C ₃ 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 attached;
R ⁵ is hydrogen atom, C ₁ -C ₄ alkyl, (C ₁ -C ₂ ) alkyl substituted by R ⁷ , C ₃ -C ₆ cycloalkyl, C ₂ -C ₄ alkenyl, C ₃ -C ₄ alkynyl , C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkylthio, —C (O) R ⁸ or C ₁ -C ₄ alkoxycarbonyl,
R ⁶ is a hydrogen atom, a halogen atom, a C ₁ -C ₄ alkyl, a C ₁ -C ₄ haloalkyl, a (C ₁ -C ₄ ) alkyl optionally substituted by R ⁹ , a C ₃ -C ₆ cycloalkyl, ₃ -C ₆ halocycloalkyl, hydroxy _(C 3 ~C ₆₎ cycloalkyl, C ₁ -C ₂ alkoxy _(C 3 ~C ₆₎ cycloalkyl, C ₄ -C ₆ cycloalkenyl, tri _(C 1 -C ₄ Alkyl) silyl, -C (R ¹⁰ ) = NOR ¹¹ , phenyl, phenyl substituted by (Z) _m , D-1, D-2, D-6, D-8, D-23, D-24, Represents D-25 or D-26,
Z is a halogen atom, cyano, nitro, -SF _5, 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 alkylsulfonyl, C ₁ -C ₄ haloalkylthio, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ haloalkylsulfonyl, D-31~D-35 or D- 37, and when m or n represents 2 or more, each Z may be the same or different from each other, and when two Zs are adjacent, the adjacent 2 One of Z is _{-CH 2 CH 2 CH 2 -,} - CH 2 CH 2 O -, - CH 2 OCH 2 -, - OCH 2 O -, - CH 2 CH 2 S (O) r -, - CH 2 CH 2 CH ₂ CH ₂ —, —CH ₂ CH ₂ CH ₂ O—, —CH ₂ CH ₂ OCH ₂ —, —CH ₂ OCH ₂ O—, —OCH ₂ CH ₂ O—, —CH ₂ CH ₂ CH ₂ S ( O) _r- , -CH ₂ CH ₂ S (O) _r CH _2- , -OCH = CH-, -SCH = CH-, -N (R ¹² ) CH = CH-, -OCH = N-, -SCH = N-, -N (R ¹² ) CH = N -, - ON = CH -, - SN = CH -, - N (R 12) N = CH -, - SN = N -, - N (R 12) N = N -, = NN (R 12) CH =, = NON =, = NSN =, -CH = CHCH = CH-, -N = CHCH = CH-, -CH = NCH = CH-, -N = NCH = CH-, -N = CHN = CH- , -N = CHCH = N-, -CH = NN = CH- or -N = NCH = N- to form a 5- or 6-membered ring with the carbon atom to which each Z is attached. At this time, the hydrogen atom bonded to each carbon atom forming a ring may be optionally substituted by a halogen atom, cyano, methyl, difluoromethyl, trifluoromethyl or methoxy,
Z ^a represents a halogen atom, methyl or trifluoromethyl,
R ⁷ represents cyano, C ₃ -C ₆ cycloalkyl, —OR ¹³ , C ₁ -C ₄ alkylthio, —C (O) NH ₂ or —C (S) NH ₂ ;
R ⁸ represents C ₁ -C ₄ alkyl or C ₃ -C ₄ cycloalkyl,
R ⁹ represents —OR ¹⁴ or —S (O) _r R ¹⁵ ;
R ¹⁰ represents a hydrogen atom or methyl,
R ¹¹ represents methyl or ethyl,
R ¹² represents C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₃ -C ₄ cycloalkylmethyl or C ₃ -C ₄ cycloalkyl,
R ¹³ represents C ₁ -C ₄ alkyl or C ₂ -C ₄ haloalkyl;
R ¹⁴ represents a hydrogen atom, methyl, ethyl or C ₁ -C ₂ haloalkyl;
R ¹⁵ represents methyl, ethyl or C ₁ -C ₂ haloalkyl;
The alkynylphenyl-substituted amide compound according to claim 1, an N-oxide or a salt thereof. G ^{1 is, G 1 -1, G 1 -2} , G 1 -3, represents a structure represented by G ¹ -4 or ^{G 1} -7,
X ¹ represents a halogen atom, difluoromethyl, trifluoromethyl or methylsulfonyl,
X ² represents a hydrogen atom,
Y ¹ represents a halogen atom,
Y ² represents a hydrogen atom or a chlorine atom,
R ¹ represents a hydrogen atom, a fluorine atom or methoxy,
R ² represents a hydrogen atom or a fluorine atom,
R ³ represents a hydrogen atom or methyl,
R ⁴ represents a hydrogen atom,
R ⁵ represents a hydrogen atom,
R ⁶ represents C ₃ -C ₆ cycloalkyl, phenyl substituted by (Z) _m , D-1, D-2, D-6, D-23 or D-25;
Z represents a halogen atom or trifluoromethyl, and when n represents 2, each Z may be the same or different from each other, and further, when two Z are adjacent to each other, May form a 6-membered ring together with the carbon atom to which each Z is attached by forming two adjacent Zs to form -CH = CHCH = CH-,
R ¹² represents C ₁ -C ₄ alkyl;
m represents 1,
n represents 0, 1 or 2;
The alkynylphenyl-substituted amide compound according to claim 2, its N-oxide or a salt thereof. G ¹ represents a structure represented by G ¹ -1;
X ¹ represents trifluoromethyl,
X ² represents a hydrogen atom;
The alkynylphenyl-substituted amide compound according to claim 1, an N-oxide or a salt thereof. G ¹ represents a structure represented by G ¹ -2 or G ¹ -3,
X ¹ represents a halogen atom, difluoromethyl, trifluoromethyl or methylsulfonyl,
The alkynylphenyl-substituted amide compound according to claim 1, an N-oxide or a salt thereof. G ¹ represents a structure represented by G ¹ -4,
X ¹ represents a halogen atom or trifluoromethyl,
The alkynylphenyl-substituted amide compound according to claim 1, an N-oxide or a salt thereof. G ¹ represents a structure represented by G ¹ -7,
X ¹ represents trifluoromethyl,
r represents 0,
The alkynylphenyl-substituted amide compound according to claim 1, an N-oxide or a salt thereof. R ⁶ represents C ₃ -C ₆ cycloalkyl;
The alkynylphenyl-substituted amide compound according to claim 1, an N-oxide or a salt thereof. R ⁶ represents phenyl substituted by (Z) _m ;
Z represents a halogen atom,
m represents 1.
The alkynylphenyl-substituted amide compound according to claim 1, an N-oxide or a salt thereof. R ⁶ represents phenyl substituted by (Z) _m ;
m represents 2 or 3,
Z has at least two adjacent positions, and two adjacent Zs together form -CH ₂ CH ₂ CH _2- , -CH ₂ CH ₂ O-, -OCH ₂ O-, -OCH ₂ CH _{2 O -, - OCH = CH} -, - SCH = CH -, - N (R 12) CH = CH -, - OCH = N -, - SCH = N -, - N (R 12) CH = N-, -ON = CH -, - SN = CH -, - N (R 12) N = CH -, - N (R 12) N = N -, = = NN (R 12) CH, = NON = or = NSN = To form a 5- or 6-membered ring together with the carbon atom to which each Z is bonded, wherein the hydrogen atom bonded to each carbon atom forming the ring is a halogen atom, methyl Or may be optionally substituted by trifluoromethyl, and when m represents 3, the remaining Z represents a halogen atom, cyano, methyl, trifluoromethyl, methoxy, difluoromethoxy or trifluoromethoxy. ,
R ¹² represents C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl,
The alkynylphenyl-substituted amide compound according to claim 1, claim 2, or claims 4 to 7, an N-oxide or a salt thereof. R ⁶ represents D-1, D-2, D-6, D-8, D-23 or D-25;
Z represents a halogen atom, methyl or trifluoromethyl, and when n represents 2, each Z may be the same or different from each other, and two Zs are adjacent In such a case, two adjacent Zs may form a 6-membered ring together with the carbon atom to which each Z is attached by forming -CH = CHCH = CH-,
R ¹² represents C ₁ -C ₄ alkyl;
n represents 0, 1 or 2;
The alkynylphenyl-substituted amide compound according to claim 1, claim 2, or claims 4 to 7, an N-oxide or a salt thereof. 12. An intermediate for producing an alkynylpyridine-substituted amide compound according to any one of claims 1 to 11, represented by the following formula (II), an N-oxide thereof, or a salt thereof.

[Wherein, Y ¹ represents a halogen atom,
Y ² represents a hydrogen atom,
R ¹ represents a hydrogen atom or a fluorine atom,
R ² represents a hydrogen atom or a fluorine atom,
R ³ represents a hydrogen atom or methyl,
R ⁴ represents a hydrogen atom,
R ⁵ represents a hydrogen atom,
R ⁶ represents D-1, D-2, D-6, D-23 or D-25;
Z represents a halogen atom or trifluoromethyl, and when n represents 2, each Z may be the same or different from each other, and further, when two Z are adjacent to each other, May form a 6-membered ring together with the carbon atom to which each Z is attached by forming two adjacent Zs to form -CH = CHCH = CH-,
R ¹² represents C ₁ -C ₄ alkyl;
n represents 0, 1 or 2. ]   A pesticidal composition comprising, as an active ingredient, at least one selected from the alkynylphenyl-substituted amide compounds according to claim 1 and N-oxides or salts thereof.   A mammal or bird antifungal or parasite control agent composition comprising as an active ingredient at least one selected from the alkynylphenyl-substituted amide compounds according to claim 1 and their N-oxides or salts.   The antifungal or parasite control composition according to claim 14 for oral administration to mammals or birds.   The antifungal or parasiticidal composition according to claim 14 for parenteral administration to mammals or birds.   The antifungal or parasiticide composition according to claim 16, wherein the method of parenteral administration to mammals or birds is administration by injection.   The antifungal or parasiticide composition according to claim 16, wherein the method of parenteral administration to mammals or birds is transdermal administration.   A fungicide or nematicide composition for agricultural and horticultural use comprising, as an active ingredient, at least one selected from the alkynylphenyl-substituted amide compounds according to claim 1 and N-oxides or salts thereof.   20. The agricultural or horticultural fungicide or nematicide composition according to claim 19, which is for foliage application to a plant.   The agricultural or horticultural fungicide or nematicide composition according to claim 19 for treating soil in which plants grow.   The agricultural or horticultural fungicide or nematicide composition according to claim 19, for treating plant seeds, tubers and rhizomes.