JP2019142778A - Alkynyl pyridine substituted amide compound and pest control agent - Google Patents

Abstract

To provide a novel pest control agent, particularly a bactericide and a nematicide.SOLUTION: The present invention provides an alkynyl pyridine substituted amide compound represented by formula (I) or a salt thereof, and a pest control agent containing the same. [Gis a structure represented by G-1, G-3, G-7 and the like; Xis a halogen atom, trifluoromethyl, methylsulfonyl or the like; Xis H, F or the like; Yis a halogen atom or the like, Yand Yare H atoms or the like, Rand Rare H atoms, F atoms, methyl or the like; Ris H, methyl or the like; Rand Rare H or the like, Ris (Z)-substituted phenyl or the like, Z is a halogen atom, C-Calkyl, haloalkyl, alkoxy, or haloalkoxy or the like, m is 1, 2, 3 or the like].SELECTED DRAWING: None

Description

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

  Conventionally, regarding alkynylpyridine-substituted amide compounds, for example, N- [2- [3-chloro-5- (2-phenylethynyl) pyridin-2-yl] -1-methylethyl] -3-difluoromethyl-1- Methyl-1H-pyrazole-4-carboxamide exhibits pesticidal activity (see Patent Document 1), for example, N- [2- [3-chloro-5- (2-phenylethynyl) pyridin-2-yl ] -2- (Isopropoxyimino) ethyl] -2- (trifluoromethyl) benzamide, N- [2- [3-chloro-5- [2- [4- (tert-butyl) phenyl] ethynyl] pyridine- 2-yl] -2- (isopropoxyimino) ethyl] -2- (trifluoromethyl) benzamide, N- [2- [3-chloro-5- [2- (2-pyridyl) ethynyl] pyridine-2- IL] -2- (Isopropoxyimino) Til] -2- (trifluoromethyl) benzamide, N- [2- [3-chloro-5- [2- (3-pyridyl) ethynyl] pyridin-2-yl] -2- (isopropoxyimino) ethyl] -2- (trifluoromethyl) benzamide and N- [2- [3-chloro-5- [2- (4-pyridyl) ethynyl] pyridin-2-yl] -2- (isopropoxyimino) ethyl] -2 -(Trifluoromethyl) benzamide exhibits pesticidal activity (see Patent Documents 2 and 3), for example, N-[[1- [3-chloro-5- (3,3,3-trifluoro- 1-propynyl) pyridin-2-yl] cyclopropyl] methyl] -3-fluoropyridine-2-carboxamide, N-[[1- [3-chloro-5- (3,3,3-trifluoro-1- Propynyl) pyridin-2-yl] cyclopropyl] methyl] -3-chloropyri 2-carboxamide, N-[[1- [3-chloro-5- (3,3,3-trifluoro-1-propynyl) pyridin-2-yl] cyclopropyl] methyl] -3-methylpyridine- 2-carboxamide and N-[[1- [3-chloro-5- (3,3,3-trifluoro-1-propynyl) pyridin-2-yl] cyclopropyl] methyl] -3- (trifluoromethyl) It is known that pyridine-2-carboxamide exhibits nematicidal activity (see Patent Document 4).

  However, no alkynylpyridine substituted amide compounds according to the present invention are disclosed, and their usefulness as pest control agents is not known.

International Publication No. 2015/125824 International Publication No. 2014/010737 Japanese Patent Laid-Open No. 2006-011286 International Publication No. 2014/173921

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

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

  As a result of intensive research aimed at solving the above-mentioned problems, the present inventors have found that a novel alkynylpyridine-substituted amide compound represented by the following formula (I) has excellent pest control activity, particularly antifungal / nematicidal activity. The present invention has been completed by finding 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 [21].

[1]
Formula (I):

Wherein, G ¹ represents a structure represented by G ¹ -1~G ¹ -16,

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 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, provided that when G ¹ represents a structure represented by G ¹ -10 and X ¹ represents dihalomethyl, X ² represents a hydrogen atom;
X ³ represents a hydrogen atom or C ₁ -C ₄ alkyl,
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 and Y ³ each independently represent a hydrogen atom, a halogen atom 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, (Z) _m Substituted phenyl (C ₁ -C ₄ ) alkoxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ haloalkylthio, C ₁ -C ₆ alkoxyamino, —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 with the carbon atoms to which R ¹ and R ² are attached, at which time the alkylene chain oxygen atom, it may contain one to two sulfur atom or nitrogen atom, and C ₁ -C ₄ alkyl group, C ₁ -C ₄ haloalkyl group, the oxo group or thioxo group may be optionally substituted Or R ¹ and R ² together form C ₁ -C ₆ alkylidene, C ₁ -C ₆ haloalkylidene or C ₁ -C ₄ alkoxy (C ₁ -C ₂ ) alkylidene. Represent,
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 to form a cyclopropyl ring with the carbon atom to which R ³ and R ⁴ are bonded,
R ⁵ is a hydrogen atom, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, (C ₁ -C ₂ ) alkyl substituted by R ⁸ , 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 9} or _C 1 -C ₄ alkoxycarbonyl Represent,
R ⁶ represents C ₃ -C ₆ cycloalkyl (C ₃ -C ₆ ) cycloalkyl, phenyl (C ₃ -C ₆ ) cycloalkyl, (Z) _m substituted phenyl or D-1 to D-29. Represent,
Further, R ¹ represents a fluorine atom, C ₁ -C ₆ alkyl or C ₁ -C ₆ alkoxy, R ² represents a fluorine atom or C ₁ -C ₆ alkyl, and R ³ represents C ₁ -C ₆ alkyl or C _When it represents _{1 to} C ₆ haloalkyl and R ⁴ represents a hydrogen atom or C _{1 to} C ₆ alkyl, R ⁶ represents a hydrogen atom, a halogen atom, C _{1 to} C ₆ alkyl, C _{1 to} C ₆ haloalkyl, (C ₁ -C ₄ ) alkyl, C ₃ -C ₁₀ cycloalkyl, C ₃ -C ₁₀ halocycloalkyl, hydroxy (C ₃ -C ₆ ) cycloalkyl, C ₁ -C ₄ optionally substituted by R ¹⁰ Alkoxy (C ₃ -C ₆ ) cycloalkyl, C ₄ -C ₁₀ cycloalkenyl, C ₄ -C ₁₀ halocycloalkenyl, tri (C ₁ -C ₄ alkyl) silyl, phenyldimethylsilyl, -C (R ¹¹ ) = May represent NOR ¹² or phenyl;
D-1 to D-29 each represent an aromatic heterocycle 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 or n represents 2 or more, representing Kirthio, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ haloalkylsulfonyl, di (C ₁ -C ₄ alkyl) amino, phenyl or D-30-D-36 Each Z may be the same as or different from each other, and when two Zs are adjacent to each other, the two adjacent Zs are —CH ₂ CH ₂ CH ₂ —, — CH ₂ CH ₂ O—, —CH ₂ OCH ₂ —, —OCH ₂ O—, —CH ₂ CH ₂ S—, —CH ₂ SCH 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-, -OCH ₂ CH ₂ S-, -SCH ₂ CH ₂ S-, -OCH = CH-, -SCH = CH-, -N (R ¹³ ) CH = CH-, -OCH = N-, -SCH = N-, -N (R ¹³ ) CH = N-,- By forming N (R ¹³ ) N = CH-, -CH = CH-CH = CH-, -N = CHCH = CH-, -N = CHCH = N- or -N = CHN = CH-, respectively. Forms a 5- or 6-membered ring with the carbon atom to which Z At best, this time, the hydrogen atoms bonded to each carbon atom forming the ring may be optionally substituted by halogen atom or C ₁ -C ₄ alkyl group,
D-30 to D-36 each represent an aromatic heterocycle represented by the following structural formula,

Z ^a represents a halogen atom, cyano, methyl, difluoromethyl or trifluoromethyl, and when n represents 2 or more, each Z ^a may be the same as or different from each other;
R ⁷ represents C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl,
R ⁸ represents cyano, —OR ¹⁴ , C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkoxycarbonyl, —C (O) NH ₂ or —C (S) NH ₂ ;
R ⁹ represents C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxymethyl, C ₃ -C ₄ cycloalkyl or C ₂ -C ₄ alkenyl,
R ¹⁰ represents cyano, —OR ¹⁵ , —S (O) _r R ¹⁶ or —N (R ¹⁸ ) R ¹⁷ ,
R ¹¹ represents a hydrogen atom or C ₁ -C ₄ alkyl;
R ¹² represents C ₁ -C ₄ alkyl;
R ¹³ represents C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl,
R ¹⁴ 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 ¹⁵ 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 ¹⁶ 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 ¹⁷ and R ¹⁸ 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, C ₃ -C ₄ alkynyl, or represents phenyl which is substituted by phenyl or (Z) _m,
Alternatively, R ¹⁷ and R ¹⁸ may form a C _{2 to} C ₅ alkylene chain together to form a 3 to 6 membered ring with the nitrogen atom to which R ¹⁷ and R ¹⁸ are bonded. represents, at this time the alkylene chain may contain one oxygen atom or sulfur atom, and C ₁ -C ₄ alkyl group, C ₁ -C ₄ haloalkyl groups, also optionally substituted by oxo group or thioxo group Often,
R ¹⁹ represents C ₁ -C ₄ alkyl, and when p represents 2, each R ¹⁹ 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. ]
An alkynylpyridine-substituted amide compound represented by the formula: N-oxide or salt thereof.

[2]
G ^{1 is, G 1 -1, G 1 -2} , G 1 -3, G 1 -4, G 1 -5, G 1 -6, G 1 -7, G 1 -8, G 1 -9, G ¹ -10, G ¹ -11, G ¹ -12, G ¹ -14 or G ¹ -16 represents a structure represented,
X ¹ represents a halogen atom, nitro, methyl, difluoromethyl, trifluoromethyl, methoxy, methylthio, methylsulfonyl, difluoromethylsulfonyl or trifluoromethylsulfonyl,
X ² represents a hydrogen atom, a fluorine atom or a chlorine atom, provided that when G ¹ represents a structure represented by G ¹ -10 and X ¹ represents difluoromethyl, X ² represents a hydrogen atom. Represent,
X ³ represents methyl,
Y ¹ represents a halogen atom or methyl;
Y ² represents a hydrogen atom or methyl,
Y ³ represents a hydrogen atom,
R ¹ is hydrogen atom, fluorine atom, C ₁ -C ₃ alkyl, C ₁ -C ₃ haloalkyl, benzyl, phenylmethyl substituted by (Z) _m , cyclopropyl, C ₁ -C ₃ alkoxy, C _1- C ₃ haloalkoxy, C ₃ -C ₄ alkenyloxy, C ₃ -C ₄ alkynyloxy, cyanomethoxy, benzyloxy, phenylmethoxy substituted by (Z) _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, which indicates that R ¹ and R ² form a cyclopropyl ring with the carbon atom to which R ¹ and R ² are bonded, or R ¹ and R ² are Together represents C ₁ -C ₂ alkylidene or C ₁ -C ₂ haloalkylidene;
R ³ represents a hydrogen atom, methyl, ethyl or fluoromethyl,
R ⁴ represents a hydrogen atom or methyl,
Alternatively, R ³ and R ⁴ together form an ethylene chain to form a cyclopropyl ring with the carbon atom to which R ³ and R ⁴ are bonded,
R ⁵ represents a hydrogen atom, cyclopropyl or methoxy,
R ⁶ represents phenyl, D-1, D-2, D-6, D-8, D-23, D-24, D-25 or D-26 substituted by (Z) _m ;
Further, when R ¹ represents a fluorine atom or C ₁ -C ₃ alkyl, R ² represents a fluorine atom or methyl, R ³ represents methyl or ethyl, and R ⁴ represents a hydrogen atom or methyl, R ⁶ is a hydrogen atom, a halogen atom, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, (C ₁ -C ₄ ) alkyl optionally substituted by R ¹⁰ , C ₃ -C ₆ cycloalkyl, C _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) May represent silyl, -C (R ¹¹ ) = NOR ¹² or phenyl;
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-33 or D- 35, when m or n represents 2 or more, each Z may be the same as or different from each other. Further, when two Zs are adjacent to each other, two Zs are adjacent to each other. Each Z forms —OCH ₂ O—, —OCH ₂ CH ₂ O— or —CH═CH—CH═CH— to form a 5- or 6-membered ring with the carbon atom to which each Z is attached. In this case, the hydrogen atom bonded to each carbon atom forming the ring is a halogen atom. Or it may be optionally substituted by a methyl group,
Z ^a represents a halogen atom, methyl or trifluoromethyl,
R ⁷ represents methyl or ethyl,
R ¹⁰ represents —OR ¹⁵ or —S (O) _r R ¹⁶ ;
R ¹¹ represents a hydrogen atom or methyl,
R ¹² represents methyl or ethyl,
R ¹⁵ represents a hydrogen atom, methyl, ethyl or C ₁ -C ₂ haloalkyl,
R ¹⁶ represents methyl, ethyl or C ₁ -C ₂ haloalkyl,
[1] Alkynylpyridine-substituted amide compounds, N-oxides or salts thereof according to [1].

[3]
G ^{1 is, G 1 -1, G 1 -2} , G 1 -3, G 1 -4, G 1 -5, G 1 -6, G 1 -7, G 1 -8, G 1 -10, G ¹ -11, G ¹ -12, G ¹ -14 or G ¹ -16 represents a structure represented,
X ¹ represents a halogen atom, nitro, methyl, difluoromethyl, trifluoromethyl, methoxy, methylthio, methylsulfonyl or difluoromethylsulfonyl,
X ² represents a hydrogen atom or a fluorine atom, provided that when G ¹ represents a structure represented by G ¹ -10 and X ¹ represents difluoromethyl, X ² represents a hydrogen atom;
Y ¹ represents a halogen atom,
Y ² represents a hydrogen atom,
R ¹ represents a hydrogen atom, a fluorine atom, methyl or methoxy,
R ² represents a hydrogen atom, a fluorine atom or methyl,
Alternatively, R ¹ and R ² together form an ethylene chain, thereby forming a cyclopropyl ring with the carbon atom to which R ¹ and R ² are bonded,
R ³ represents a hydrogen atom or methyl,
R ⁴ represents a hydrogen atom or methyl,
R ⁵ represents a hydrogen atom or cyclopropyl,
R ⁶ represents (Z) _m substituted phenyl, D-1, D-2, D-6, D-8, D-23 or D-25;
Further, when R ¹ represents a fluorine atom, R ² represents a fluorine atom, R ³ represents methyl, and R ⁴ represents a hydrogen atom or methyl, R ⁶ represents C ₁ -C ₄ haloalkyl or C ₃ -C ₆ cycloalkyl may represent,
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, represents C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ haloalkylthio, C ₁ -C ₄ haloalkylsulfinyl or _C 1 -C ₄ haloalkylsulfonyl, when m or n is 2 or more, Each Z may be the same as or different from each other. Further, when two Zs are adjacent to each other, the two adjacent Zs are —OCH ₂ O— or —CH═CH—CH═. By forming CH-, a 5-membered ring or a 6-membered ring may be formed together with the carbon atom to which each Z is bonded. At this time, the hydrogen atom bonded to each carbon atom forming the ring is a halogen atom. Optionally substituted by
R ⁷ represents methyl,
R ¹³ represents C ₁ -C ₄ alkyl;
m represents 1, 2 or 3;
n represents 0, 1 or 2;
[2] The alkynylpyridine-substituted amide compound according to [2].

[4]
G ¹ represents the structure represented by G ¹ -1,
X ¹ represents a halogen atom, methyl or trifluoromethyl,
X ² represents a hydrogen atom or a fluorine atom,
[1] to [3] alkynylpyridine-substituted amide compounds, N-oxides or salts thereof.

[5]
G ¹ represents a structure represented by G ¹ -2 or G ¹ -3,
X ¹ represents a halogen atom, methyl, difluoromethyl, trifluoromethyl, methylthio, methylsulfonyl or difluoromethylsulfonyl,
[1] to [3] alkynylpyridine-substituted amide compounds, N-oxides or salts thereof.

[6]
G ¹ represents the structure represented by G ¹ -4,
X ¹ represents a halogen atom or trifluoromethyl,
[1] to [3] alkynylpyridine-substituted amide compounds, N-oxides or salts thereof.

[7]
G ¹ represents a structure represented by G ¹ -7 or G ¹ -8,
X ¹ represents a halogen atom, methyl or trifluoromethyl,
[1] to [3] alkynylpyridine-substituted amide compounds, N-oxides or salts thereof.

[8]
G ¹ represents a structure represented by G ¹ -10;
X ¹ represents difluoromethyl or trifluoromethyl,
X ² represents a hydrogen atom,
R ⁷ represents methyl,
[1] to [3] alkynylpyridine-substituted amide compounds, N-oxides or salts thereof.

[9]
R ⁶ represents (Z) _m substituted phenyl, D-1, D-2, D-6, D-8, D-23 or D-25;
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, represents C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ haloalkylthio, C ₁ -C ₄ haloalkylsulfinyl or _C 1 -C ₄ haloalkylsulfonyl, when m or n is 2 or more, Each Z may be the same as or different from each other. Further, when two Zs are adjacent to each other, the two adjacent Zs are —OCH ₂ O— or —CH═CH—CH═. By forming CH-, a 5-membered ring or a 6-membered ring may be formed together with the carbon atom to which each Z is bonded. At this time, the hydrogen atom bonded to each carbon atom forming the ring is a halogen atom. Optionally substituted by
R ¹³ represents C ₁ -C ₄ alkyl;
m represents 1, 2 or 3;
n represents 0, 1 or 2;
[1] to [8] alkynylpyridine-substituted amide compounds, N-oxides or salts thereof.

[10]
R ¹ represents a fluorine atom,
R ² represents a fluorine atom,
R ³ represents methyl,
R ⁴ represents a hydrogen atom,
R ⁶ represents C ₁ -C ₄ haloalkyl or C ₃ -C ₆ cycloalkyl,
[1] to [8] alkynylpyridine-substituted amide compounds, N-oxides or salts thereof.

[11]
Formula (II):

[Wherein Y ¹ represents a halogen atom,
Y ² represents a hydrogen atom,
Y ³ represents a hydrogen atom,
R ¹ represents a hydrogen atom, a fluorine atom, methyl or methoxy,
R ² represents a hydrogen atom, a fluorine atom or methyl,
Alternatively, R ¹ and R ² together form an ethylene chain, thereby forming a cyclopropyl ring with the carbon atom to which R ¹ and R ² are bonded,
R ³ represents a hydrogen atom or methyl,
R ⁴ represents a hydrogen atom or methyl,
R ⁵ represents a hydrogen atom or cyclopropyl,
R ⁶ represents (Z) _m substituted phenyl, D-1, D-2, D-6, D-8, D-23 or D-25;
Further, when R ¹ represents a fluorine atom, R ² represents a fluorine atom, R ³ represents methyl, and R ⁴ represents a hydrogen atom or methyl, R ⁶ represents a C ₁ -C ₄ haloalkyl, C ₃ -C ₆ cycloalkyl or tri _(C 1 -C ₄ alkyl) may be a silyl,
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, represents C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ haloalkylthio, C ₁ -C ₄ haloalkylsulfinyl or _C 1 -C ₄ haloalkylsulfonyl, when m or n is 2 or more, Each Z may be the same as or different from each other. Further, when two Zs are adjacent to each other, the two adjacent Zs are —OCH ₂ O— or —CH═CH—CH═. By forming CH-, a 5-membered ring or a 6-membered ring may be formed together with the carbon atom to which each Z is bonded. At this time, the hydrogen atom bonded to each carbon atom forming the ring is a halogen atom. Optionally substituted by
R ¹³ represents C ₁ -C ₄ alkyl;
m represents 1, 2 or 3;
n represents 0, 1 or 2. ]
An intermediate for producing an alkynylpyridine-substituted amide compound according to [1] to [10]

[12]
A pesticidal composition containing as an active ingredient at least one selected from the alkynylpyridine-substituted amide compounds according to [1] to [10] or salts thereof.

[13]
[1] A mammal or avian antifungal or parasite control agent composition comprising, as an active ingredient, one or more selected from the alkynylpyridine-substituted amide compounds according to [1] to [10] or salts thereof.

[14]
The endoparasite control composition according to [13] for oral administration to mammals or birds.

[15]
The endoparasite control agent composition according to [13] for parenteral administration to mammals or birds.

[16]
The endoparasite control composition according to [15], wherein the parenteral administration to mammals or birds is administration by injection.

[17]
The endoparasite control composition according to [15], wherein the parenteral administration to mammals or birds is transdermal administration.

[18]
An agricultural and horticultural fungicide or nematicide composition containing, as an active ingredient, one or more selected from the alkynylpyridine-substituted amide compounds according to [1] to [10] or salts thereof.

[19]
[18] The agricultural and horticultural fungicide or nematicide composition for spraying foliage on plants.

[20]
[18] The agricultural or horticultural fungicide or nematicide composition for treating soil on which plants grow.

[21]
[18] The agricultural or horticultural fungicide or nematicide composition for treating plant seeds, tuberous roots and rhizomes.

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

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

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

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

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

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

In the present specification, the expression “C _a -C _b haloalkyl” is a linear or branched chain having a carbon number of _a to _b, wherein a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom. In this case, when substituted by two or more halogen atoms, these halogen atoms may be the same as or different from each other. For example, fluoromethyl group, chloromethyl group, bromomethyl group, iodomethyl group, difluoromethyl group, dichloromethyl group, trifluoromethyl group, chlorodifluoromethyl group, trichloromethyl group, bromodifluoromethyl group, 1-fluoroethyl group, 2- Fluoroethyl group, 2-chloroethyl group, 2-bromoethyl group, 1,1-difluoroethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, 2-chloro-2,2-difluoro Ethyl group, 2,2,2-trichloroethyl group, 2-bromo-2,2-difluoroethyl group, 1,1,2,2-tetrafluoroethyl group, 2-chloro-1,1,2-trifluoro Ethyl group, pentafluoroethyl group, 2,2-difluoropropyl group, 3,3,3-trifluoropropyl group, 3-bromo-3,3-difluoropropyl group, 2,2,3,3- Trifluoropropyl group, 2,2,3,3,3-pentafluoropropyl group, 1,1,2,3,3,3-hexafluoropropyl group, heptafluoropropyl group, 2,2,2-trifluoro -1-methylethyl group, 2,2,2-trifluoro-1- (trifluoromethyl) ethyl group, 1,2,2,2-tetrafluoro-1- (trifluoromethyl) ethyl group, 2,2 , 2-trifluoro-1,1-dimethylethyl group, 2,2,3,4,4,4-hexafluorobutyl group, 2,2,3,3,4,4,4-heptafluorobutyl group, Nonafluorobutyl groups and the like are listed as specific examples, and each is selected within the range of the designated number of carbon atoms.

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

In the present specification, the expression “C _a -C _b halocycloalkyl” is a cyclic hydrocarbon group having a carbon number of _a to _b , wherein a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom And a monocyclic or complex ring structure from 3 to 10-membered rings can be formed. Each ring may be optionally substituted with an alkyl group 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, They may be both, and when they are substituted by two or more halogen atoms, the halogen atoms may be the same as or different from each other. For example, 1-fluorocyclopropyl group, 1-chlorocyclopropyl group, 2-chlorocyclopropyl group, 2,2-difluorocyclopropyl group, 2,2-dichlorocyclopropyl group, 2,2-dibromocyclopropyl group, 2 , 2-Difluoro-1-methylcyclopropyl group, 2,2-dichloro-1-methylcyclopropyl group, 2,2-dibromo-1-methylcyclopropyl group, 3-fluorocyclobutyl group, 2,2,3 Specific examples include 1,3-tetrafluorocyclobutyl group, 1-fluorocyclopentyl group, 1-chloro-2,2-dimethylcyclopropyl group, 1-fluorocyclohexyl group, etc. Selected.

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

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

In the present specification, the expression “C _a -C _b cycloalkenyl” represents an unsaturated hydrocarbon group which is cyclic and has one or two or more double bonds. A monocyclic or complex ring structure from a 3-membered ring to a 10-membered ring can be formed. Each ring may be optionally substituted with an alkyl group within the range of the specified number of carbon atoms, and the double bond may be either endo- or exo-. Specific examples include 1-cyclopentenyl group, 2-cyclopentenyl group, 1-cyclohexenyl group, 2-cyclohexenyl group, bicyclo [2.2.1] -5-hepten-2-yl group, and the like. Each selected range of carbon atoms is selected.

In the present specification, the expression “C _a -C _b halocycloalkenyl” refers to a cyclic and intramolecular structure in which a hydrogen atom bonded to a carbon atom is arbitrarily substituted with a halogen atom and the number of carbon atoms is a to b. Represents an unsaturated hydrocarbon group having one or more double bonds, and can form a monocyclic or complex ring structure having 3 to 10 members. Each ring may be optionally substituted with an alkyl group within the range of the specified number of carbon atoms, and the double bond may be either endo- or exo-. At this time, when substituted by two or more halogen atoms, these halogen atoms may be the same as or different from each other. For example, a 2-chloro-1-cyclobutenyl group, a 2-bromo-1-cyclopentenyl group, and the like are given as specific examples, and each is selected within the range of the designated number of carbon atoms.

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

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

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

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

In the present specification, the expression “C _a -C _b alkenyloxy” represents an alkenyl-O— group having the above-mentioned meaning consisting of _a to _b carbon atoms, for example, 2-propenyloxy group, 2-butenyloxy. Specific examples include a group, 1-methyl-2-propenyloxy group, 2-methyl-2-propenyloxy group, 3-methyl-2-butenyloxy group, 1,1-dimethyl-2-propenyloxy group, and the like. Each selected range of carbon atoms is selected.

In the present specification, the expression “C _a -C _b haloalkenyloxy” represents a haloalkenyl-O— group having the above-mentioned meaning consisting of _a to _b carbon atoms, for example, 2-fluoro-2-propenyl. Oxy group, 2-chloro-2-propenyloxy group, 3-chloro-2-propenyloxy group, 3,3-difluoro-2-propenyloxy group, 2,3-dichloro-2-propenyloxy group, 3,3 Specific examples include -dichloro-2-propenyloxy group, 2,3,3-trifluoro-2-propenyloxy group, and the like, and each is selected within the range of the designated number of carbon atoms.

In the present specification, the expression “C _a -C _b alkynyloxy” represents an alkynyl-O— group having the above-mentioned meaning consisting of _a to _b carbon atoms, for example, 2-propynyloxy group, 2-butynyloxy Specific examples include a group, a 1-methyl-2-propynyloxy group, a 1,1-dimethyl-2-propynyloxy group, and the like, and each is selected within the range of the designated number of carbon atoms.

In the present specification, the expression “C _a -C _b haloalkynyloxy” represents a haloalkynyl-O— group having the above-mentioned meaning consisting of _a to _b carbon atoms, such as 3-chloro-2-propynyl. Specific examples include an oxy group, a 3-bromo-2-propynyloxy group, a 3-iodo-2-propynyloxy group, and the like, and each is selected within the range of the designated number of carbon atoms.

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

In the present specification, the expression “C _a -C _b alkylsulfinyl” represents an alkyl-S (O) — group having the above-mentioned meaning consisting of _a to _b carbon atoms, such as methylsulfinyl group, ethylsulfinyl group. Specific examples include a group, an n-propylsulfinyl group, an i-propylsulfinyl group, and the like, and each is selected within the range of the designated number of carbon atoms.

In the present specification, the expression “C _a -C _b alkylsulfonyl” represents an alkyl-SO ₂ -group having the above-mentioned meaning consisting of _a to _b carbon atoms, such as a methylsulfonyl group, an ethylsulfonyl group, Specific examples include n-propylsulfonyl group, i-propylsulfonyl group and the like, and each is selected within the range of the designated number of carbon atoms.

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

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

In the present specification, the expression “C _a -C _b haloalkylsulfonyl” represents a haloalkyl-SO ₂ -group having the above-mentioned meaning consisting of _a to _b carbon atoms, such as a difluoromethylsulfonyl group, trifluoromethyl, and the like. A sulfonyl group etc. are mentioned as a specific example, It selects in the range of each designated carbon atom number.

In the present specification, the expression “di (C _a -C _b alkyl) amino” means that the number of carbon atoms may be the same or different from each other, and the number of carbon atoms may be ab. Represents an amino group substituted by an alkyl group such as dimethylamino group, ethyl (methyl) amino group, diethylamino group, di (n-propyl) amino group, etc. Selected in a range of numbers.

In the present specification, the expression “C _a -C _b alkoxyamino” represents an alkyl-ONH-group having the above-mentioned meaning consisting of _a to _b carbon atoms, for example, methoxyamino group, ethoxyamino group, n Specific examples include -propyloxyamino group, i-propyloxyamino group, n-butyloxyamino group, i-butyloxyamino group, sec-butyloxyamino group, tert-butyloxyamino group, etc. Selected within the specified number of carbon atoms.

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

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

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

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

In the present specification, “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 halo” alkoxy _(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 _b haloalkylsulfonyl (C _d -C _e ) alkyl”, “phenyl (C _d -C _e ) alkyl” or “(Z) _m- substituted phenyl (C _d -C _e ) alkyl” notation, any cyano group is the meaning of each, C _a -C _b alkoxy group, C _a -C _b c Alkoxy groups, C _a -C _b alkylthio group, C _a -C _b alkylsulfinyl group, C _a -C _b alkylsulfonyl group, C _a -C _b haloalkylthio group, C _a -C _b haloalkylsulfinyl group, C _a ~ C _b haloalkylsulfonyl group, by a phenyl group substituted by a phenyl group or (Z) _m, the meaning of the number of methyl group or a carbon atom bonded hydrogen atom is optionally substituted carbon atom consisting d~e pieces Each selected from a range of each specified number of carbon atoms.

In the present specification, the expression “(C _a -C _b ) alkyl substituted by R ⁸ ” indicates that the number of carbon atoms in which a hydrogen atom bonded to a carbon atom is substituted by any R ⁸ is from _a to _b. The above-mentioned meaning is an alkyl group, and each is selected within the range of the designated number of carbon atoms.

In this specification, the expression “(C _a -C _b ) alkyl optionally substituted with R ¹⁰ ” refers to the number of carbon atoms in which a hydrogen atom bonded to a carbon atom is optionally substituted with any R ¹⁰ . Represents an alkyl group as defined above consisting of ˜b and is selected within the range of each specified number of carbon atoms. At this time, when two or more substituents R ¹⁰ on each (C _a -C _b ) alkyl group are present, each R ¹⁰ may be the same as or different from each other.

As used herein, “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 (C _d -C _e ) cycloalkyl is any C _a -C _b cycloalkyl group, hydroxyl group, any C _a -C _b alkoxy group as defined above, A cycloalkyl group having the above-mentioned meaning consisting of d to e carbon atoms, in which a hydrogen atom bonded to a carbon atom is substituted by a phenyl group, is selected within the range of each designated number of carbon atoms.

In the present specification, the expression “C _a -C _b alkylidene” represents a linear or branched hydrocarbon group having a carbon number of _a to _b and bonded by a double bond, for example, a methylidene group Specific examples include ethylidene group, propylidene group, 1-methylethylidene group, butylidene group, 1-methylpropylidene group, pentylidene group, 1-methylbutylidene group, 1-ethylethylidene group, hexylidene group, etc. Is selected within the range of the specified number of carbon atoms.

In the present specification, the expression “C _a -C _b haloalkylidene” refers to a straight or branched chain having _a to _b carbon atoms in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom The chain represents a hydrocarbon group bonded by a double bond. At this time, when substituted with two or more halogen atoms, the halogen atoms may be the same as or different from each other. For example, a fluoromethylidene group, a chloromethylidene group, a difluoromethylidene group, a dichloromethylidene group, a 2,2,2-trifluoroethylidene group, and the like are given as specific examples, and each is selected in the range of the designated number of carbon atoms. .

In the present specification, the expression “C _a -C _b alkoxy (C _d -C _e ) alkylidene” indicates that a hydrogen atom bonded to a carbon atom is substituted by any C _a -C _b alkoxy group having the above-mentioned meaning. Represents an alkylidene group having the above meaning consisting of d to e carbon atoms, and is selected in the range of the respective designated carbon atoms.

In the present specification, the notation of “cyano (C _a -C _b ) alkoxy”, “phenyl (C _a -C _b ) alkoxy” or “(Z) _m- substituted phenyl (C _a -C _b ) alkoxy” is , A cyano group, a phenyl group or a phenyl group substituted by (Z) _m represents an alkoxy group having the above-mentioned meaning, wherein the hydrogen atom bonded to the carbon atom is substituted with a to b carbon atoms, Each selected range of carbon atoms is selected.

In the present specification, “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 bonded. In some cases, the alkylene chain may contain one or two oxygen atoms, sulfur atoms or nitrogen atoms. Specific examples of notation include, for example, cyclopropane, oxirane, thiirane, aziridine, cyclobutane, oxetane, thietane, azetidine, and cyclopentane. , Oxolane, thiolane, pyrrolidine, dioxolane, dithiolane, cyclohexane, tetrahydropyran, tetrahydrothiopyran, piperidine, 1,3-dioxane, 1,3-dithiane, etc. Is done.

In the present specification, “R ¹⁷ and R ¹⁸ together form a C _{2 to} C ₅ alkylene chain to form a 3 to 6 membered ring with the nitrogen atom to which R ¹⁷ and R ¹⁸ are bonded. In this case, the alkylene chain may contain one oxygen atom or sulfur atom. Specific examples of the notation include, for example, aziridine, azetidine, pyrrolidine, oxazolidine, thiazolidine, piperidine, and 2H-3,4. , 5,6-tetrahydro-1,3-oxazine, morpholine, 2H-3,4,5,6-tetrahydro-1,3-thiazine, thiomorpholine, etc. Selected.

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

That is, G ¹ -I: G ¹ -1 [where X ¹ represents a halogen atom, nitro, methyl, trifluoromethyl, or methylsulfonyl, and 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 [wherein X ¹ represents a halogen atom, methyl, difluoromethyl, trifluoromethyl, methylthio, methylsulfonyl or difluoromethylsulfonyl. ].

G ¹ -IV: G ¹ -4 [where X ¹ represents a halogen atom or trifluoromethyl. ].

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

G ¹ -VI: G ¹ -10 [where X ¹ represents difluoromethyl or trifluoromethyl, X ² represents a hydrogen atom, and R ⁷ represents methyl. ].

G ¹ -VII: G ¹ -14 [wherein X ¹ represents difluoromethyl or trifluoromethyl, and X ³ represents methyl. ].

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 [wherein X ¹ represents methoxy 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 [wherein X ¹ represents difluoromethyl or trifluoromethyl, and X ³ represents a hydrogen atom or methyl. ].

G ¹ -XII: G ¹ -7 and G ¹ -8 [where X ¹ represents difluoromethyl. ].

G ¹ -XIII: G ¹ -9 [wherein X ¹ represents difluoromethyl or trifluoromethyl, and R ⁷ represents methyl. ].

G ¹ -XIV: G ¹ -10 [where X ¹ represents methyl, ethyl or trifluoromethyl, X ² represents a fluorine atom or a chlorine atom, and R ⁷ represents methyl. ].

G ¹ -XV: G ¹ -11 and G ¹ -12 [where X ¹ represents difluoromethyl or trifluoromethyl, and X ³ represents a hydrogen atom or methyl. ].

G ¹ -XVI: G ¹ -13 [where X ¹ represents difluoromethyl or trifluoromethyl, and X ³ represents methyl. ].

G ¹ -XVII: G ¹ -15 [where X ¹ represents difluoromethyl or trifluoromethyl, and R ⁷ represents methyl. ].

G ¹ -XVIII: G ¹ -16 [wherein X ¹ represents methyl or trifluoromethyl, and r represents 0, 1 or 2. ].

Of these, ^{G 1} -I~G ¹ -VII as range of the substituent of ^{G 1, G 1 -XI, G} 1 -XIII, more preferably G ¹ -XVII and ^{G 1} -xviii, further , G ¹ -I~G ¹ -VII is particularly preferred.

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

That, YI: Y ¹ is a halogen atom, and ^{Y 2} and ^{Y 3} are simultaneously hydrogen atom.

Y-II: Y ¹ is methyl, and Y ² and Y ³ are simultaneously hydrogen atoms.

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

Among these, YI and Y-II are more preferable as a combination of substituents represented by Y ¹ , Y ² and Y ³ , and YI is particularly preferable.

In the compounds included in the present invention, examples of combinations of preferable ranges of substituents represented by R ¹ , R ² , R ³ and R ⁴ include the following groups of RI to R-XV.

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: phenylmethyl wherein R ¹ is substituted by (Z) _m [wherein Z represents a halogen atom, m represents 1 or 2, and when m represents 2, each Z is They may be the same or different from each other. ] And cyclopropyl, and R ² , R ³ and R ⁴ are hydrogen atoms.

R-III: R ¹ is a fluorine atom, methyl, methoxy, 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 .

R-IV: R ¹ and R ² are each independently a fluorine atom and methyl, and R ³ and R ⁴ are hydrogen atoms.

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

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

R-VII: R ¹ and R ² together form C ₁ -C ₂ alkylidene or C ₁ -C ₂ haloalkylidene, and R ³ and R ⁴ are hydrogen atoms.

R-VIII: R ¹ and R ² are hydrogen atoms, R ³ is ethyl and fluoromethyl, and R ⁴ is a hydrogen atom.

R-IX: a carbon atom to which R ³ and R ⁴ are bonded by R ¹ and R ² being a hydrogen atom and R ³ and R ⁴ being methyl or R ³ and R ⁴ being combined to form an ethylene chain Together with the cyclopropyl ring.

RX: phenylmethyl substituted with R ¹ is C ₁ -C ₃ alkyl, C ₁ -C ₃ haloalkyl, benzyl and (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 Each Z may be the same as or different from each other. And R ² , R ³ and R ⁴ are hydrogen atoms.

R-XI: R ¹ is replaced 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 [Wherein Z is a halogen atom, cyano, nitro, methyl, trifluoromethyl, methoxy, difluoromethoxy, trifluoromethoxy, methylthio, methylsulfinyl, methylsulfonyl, difluoromethylthio, difluoromethylsulfonyl, trifluoromethylthio] Alternatively, it represents trifluoromethylsulfonyl, m represents 1 or 2, and when m represents 2, each Z may be the same as 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 is C ₁ -C ₃ alkyl, R ² is a hydrogen atom, R ³ is methyl, and R ⁴ is a hydrogen atom.

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

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

Of these, RI to R-VII, R-VIII, and R-XI are more preferable as combinations of the ranges of substituents represented by R ¹ , R ² , R ^3, and R ^4. -III to RV, R-VI and R-VII are particularly preferred.

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

That is, R ⁵ -I: a hydrogen atom.

R ⁵ -II: cyclopropyl.

R ⁵ -III: Methoxy.

Of these, more preferred R ⁵ -I and R ⁵ -II as range of the substituent of R ^5, further, R ⁵ -I is particularly preferred.

In the compounds included in the present invention, examples of the preferred range of the substituent represented by R ⁶ include the following groups.

That is, R ⁶ -I: C ₁ -C ₄ alkyl.

R _⁶ -II: C ₃ ~C ⁶ cycloalkyl.

R ⁶ -III: optionally substituted by R ¹⁰ _(C 1 _{~C 4)} alkyl [wherein, R ¹⁰ represents -OR ^15, R ¹⁵ is a hydrogen atom, methyl, ethyl or _C 1 -C ₂ haloalkyl Represents. ].

R ⁶ -IV: Tri (C ₁ -C ₄ alkyl) silyl.

R ⁶ -V: —CH═NOR ¹² [wherein R ¹² represents methyl or ethyl. ].

R ⁶ -VI: phenyl.

R ⁶ -VII: (Z) phenyl substituted by _m [where Z is a halogen atom, cyano, nitro, C ₁ -C ₄ alkyl, trifluoromethyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ Represents haloalkoxy, methylthio, methylsulfinyl, methylsulfonyl, trifluoromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, and when m represents 2 or 3, each Z may be the same as or Further, when two Zs are adjacent to each other, the two adjacent Zs form —OCH ₂ O— or —CH═CH—CH═CH—, so that each Z A 5-membered ring or a 6-membered ring may be formed together with the carbon atoms to be bonded. At this time, the hydrogen atom bonded to each carbon atom forming the ring is optionally substituted with a fluorine atom or a methyl group. At best, m represents 1, 2 or 3. ].

R ⁶ -VIII: D-1, D-2, D-6, D-8 and D-23 [wherein Z represents a halogen atom, C ₁ -C ₄ alkyl or trifluoromethyl, and n is 2. When represented, each Z may be the same as or different from each other, R ¹³ represents C ₁ -C ₄ alkyl, and n represents 0, 1 or 2. ].

R ⁶ -IX: a hydrogen atom.

R ⁶ -X: a halogen atom and a C ₁ -C ₄ haloalkyl.

R ⁶ -XI: optionally substituted by R ¹⁰ _(C 1 _{~C 4)} alkyl [wherein, R ¹⁰ represents ^{_{-S (O) r R 16,}} R 16 is methyl, ethyl or _C 1 -C Represents ₂ haloalkyl, r represents 0, 1 or 2; ].

R _⁶ -XII: C ₃ ~C ⁶ halocycloalkyl.

R ⁶ -XIII: —C (R ¹¹ ) = NOR ¹² [wherein R ¹¹ represents methyl and R ¹² represents methyl or ethyl. ].

R ⁶ -XIV: (Z) phenyl substituted by _m , wherein Z is a halogen atom, methyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylsulfinyl, C _1- It represents C ₄ alkylsulfonyl, C ₁ -C ₄ haloalkylthio, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ haloalkylsulfonyl, D-31~D-33 or D-35, m represents 2 or 3 In each case, each Z may be the same as or different from each other, Z ^a represents a halogen atom, methyl or trifluoromethyl, m represents 1, 2 or 3 and n represents 0 Or 1 is represented. ].

R ⁶ -XV: 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 _{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 when n represents 2, each Z may be the same as or They may be different from each other, R ¹³ represents C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl, and n represents 0, 1 or 2. ].

Of these, ^R R ⁶ -I~R ⁶ as range of the substituent of ^{6 -VIII, R 6 -X, R} 6 -XII, R 6 -XIV and ^{R 6} -XV more preferably, further , R ⁶ -I~R ⁶ -VIII are particularly preferred.

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

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

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

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

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

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

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

  Chipidiomycota fungi such as Olpidium spp.

  Blastocladiomycota fungi such as Physoderma spp.

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

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

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

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

  Firmicutes gram-positive fungi such as Clostridium sp.

  Tenericutes gram-positive fungi such as Phytoplasma.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

  Amoeba such as Entamoeba histolytica (E. invadens).

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

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

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

  Vestibuliferida ciliates such as large colonic barantidium coli.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

  Manufacturing method A

Formula (II) [wherein Y ¹ , Y ² , Y ³ , 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, p-toluenesulfonate, etc.) and a compound represented by formula (III) [wherein G ¹ Represents the same meaning as described above, and J ¹ represents a chlorine atom, a bromine atom, a C _{1 to} C ₄ alkylcarbonyloxy group (for example, pivaloyloxy group), a C _{1 to} C ₄ alkoxycarbonyloxy group (for example, isobutyloxycarbonyloxy group). ) Or an azolyl group (for example, imidazol-1-yl group). ], If necessary, benzene, toluene, dichloromethane, chloroform, 1,2-dichloroethane, diethyl ether, tert-butyl methyl ether, tetrahydrofuran, 1,4-dioxane, ethyl acetate, N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, water, or a mixture of two or more of them in an arbitrary ratio is used as a solvent. If necessary, 1 to 3 equivalents of carbonic acid per 1 equivalent of the compound represented by formula (II) In the temperature range from 0 ° C. to the reflux temperature of the reaction mixture in the presence of a base such as sodium, potassium carbonate, sodium bicarbonate, sodium acetate, triethylamine, ethyldiisopropylamine, N-methylmorpholine, pyridine, 4- (dimethylamino) pyridine, etc. by reacting 30 minutes to 24 hours, the formula (I) ^{[wherein, G 1, Y 1, Y} 2, Y ^{, R 1, R 2, R} 3, R 4, R 5 and ^{R 6} are as defined above. This invention compound represented by this can be obtained.

  Some of the compounds represented by the formula (III) used here are known compounds, and some of them are commercially available. In addition, other 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 known 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.] In accordance with the method described in 1991, 34, 222, etc., a corresponding known carboxylic acid and an organic acid halide such as pivaloyl chloride or isobutyl chloroformate are required. For example, a method of reacting in the presence of a base, or The Journal of Organic Chemistry [J. Org. Chem.] 1989, 54 According to 5620 pages, etc., and the corresponding known carboxylic acids, it can be synthesized using a method in which reacting a carbonyldiimidazole or sulfonyl diimidazole, etc..

  Manufacturing method B

Formula (Ia) wherein R ⁵ is a hydrogen atom in formula (I) [wherein G ¹ , Y ¹ , Y ² , Y ³ , R ¹ , R ² , R ³ , R ⁴ and R ⁶ are the same as above. Represents meaning. The compound of the present invention represented by formula (1a) and 1 equivalent of the compound represented by formula (Ia) are 1 to 10 equivalents of formula (IV) [wherein R ⁵ is a hydrogen atom, —OH, C ₁ -C ₄ represents the same meaning as alkoxy and _C 1 -C ₄ the non-haloalkoxy, J ² is a chlorine atom, a bromine atom, an iodine atom, C ₁ -C ₄ alkylcarbonyloxy group (e.g., pivaloyloxy group) , C ₁ -C ₄ alkyl sulfonate group (e.g., such as methanesulfonyloxy group), C ₁ -C ₄ haloalkylsulfonate group (e.g., trifluoromethanesulfonyloxy group), an aryl sulfonate group (e.g., benzenesulfonyloxy group, p A good leaving group such as -toluenesulfonyloxy group and the like or azolyl group (for example, imidazol-1-yl group and the like). The compound represented by the formula (Ia) is used if necessary using a polar solvent such as tert-butyl methyl ether, tetrahydrofuran, 1,4-dioxane, acetonitrile or N, N-dimethylformamide. In the presence of a base such as 1 to 3 equivalents of sodium hydride, potassium tert-butoxide, potassium hydroxide, potassium carbonate, triethylamine, pyridine, etc. By reacting for a time, formula (I) [wherein G ¹ , Y ¹ , Y ² , Y ³ , R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ represent the same meaning as described above. . This invention compound represented by this can be obtained.

  Some of the compounds represented by the formula (IV) used here are known compounds, and some of them are commercially available. Other than the above, general synthesis methods described in the literature, for example, Chemical and Pharmaceutical Bulletin [Chem. Pharm. Bull.] 1986, 34, 540 and 2001, 49, 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, Japan Those described in the National Patent Publication (JP H05-125017), European Patent Publication (EP 0,051,273 Publication), British Patent Publication (GB 2,161,802 Publication), etc. It can be synthesized in accordance with the.

  Manufacturing method C

Formula (V) [wherein G ¹ , Y ¹ , Y ² , Y ³ , R ¹ , R ² , R ³ , R ⁴ and R ⁵ represent the same meaning as described above, J ³ represents a chlorine atom, a bromine atom And a good leaving group such as an iodine atom or a C ₁ -C ₄ haloalkylsulfonate group (for example, trifluoromethanesulfonyloxy group and the like). The reaction conditions for general Sonogashira coupling described in, for example, European Journal of Organic Chemistry [Eur. J. Org. Chem.] 2015, 2015, 4389, etc. And formula (VI) [wherein R ⁶ represents the same meaning as described above, and Q represents a hydrogen atom. Or a compound represented by the formula (V) and the formula (VI) [wherein R ⁶ represents the same meaning as described above, and Q represents a trimethylsilyl group or the like. Or a substituted acetylene represented by the formula, for example, in accordance with International Patent Application Publication (WO 2005/094822), etc., in the presence of tetrabutylammonium fluoride under the reaction conditions of Sonogashira coupling, or The compound represented by the formula (V) can be prepared by reacting the compound represented by the formula (VI) [wherein R is a compound under the general Negishi coupling reaction conditions described in Heterocycles 1997, 46, 209, etc. ⁶ represents the same meaning as described above, and Q represents a —ZnCl group, —ZnBr group, —ZnI group or the like. And a substituted acetylene represented by formula (I) [wherein G ¹ , Y ¹ , Y ² , Y ³ , R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ^6] Represents the same meaning as above. This invention compound represented by this can be obtained.

  Some of the compounds represented by the formula (V) used here are, for example, International Patent Application Publication (WO 2005/014545 Publication), International Patent Application Publication (WO 2013/064461 Publication), International Patent Application Publication ( WO 2013/064521) and the like, and other compounds can be synthesized in the same manner as known compounds.

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

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

  The compound represented by the formula (II) used in the production method A can be synthesized, for example, as shown in Reaction Scheme 1 to Reaction Scheme 10.

  Reaction formula 1

Formula (VII) [wherein Y ¹ , Y ² , Y ³ , R ¹ , R ² and J ³ represent the same meaning as described above. ], For example, according to the method described in Bioorganic & Med. Chem. Lett. 2012, Vol. 22, p. 6108, etc., diisobutylaluminum hydride, etc. And then reacting with di-tert-butyl dicarbonate to give a compound of formula (VIII) [wherein Y ¹ , Y ² , Y ³ , R ¹ , R ² and J ³ are Represents the same meaning. ] Can be synthesized.

Subsequently, the compound represented by the formula (VIII) is represented by the formula (VI) [wherein R ⁶ represents the same meaning as described above, and Q represents a hydrogen atom, a trimethylsilyl group or the like. For example, Organic and Biomolecular Chemistry [Org. Biomol. Chem.] 2002, 12, 185, Journal of Medicinal Chemistry [J. Med. Chem.] 2009 The reaction is carried out using the Sonogashira coupling reaction conditions described in Y., Vol. 52, p. 3563, etc. to formula (IX) [wherein Y ¹ , Y ² , Y ³ , R ¹ , R ² and R ⁶ Represents the same meaning as above. ] Can be synthesized.

The compounds represented by the formula (IX) thus obtained are, for example, European Patent Publication (EP 1,574,511 Publication), International Patent Application Publication (WO 2008/021927 Publication), International Patent Application Publication (WO 2010 / In the formula (II), R ³ , R ⁴ and R ⁵ are hydrogen atoms by reacting with hydrochloric acid, hydrobromic acid, trifluoroacetic acid or the like according to the method described in JP A certain formula (IIa) [wherein Y ¹ , Y ² , Y ³ , R ¹ , R ² and R ⁶ represent the same meaning as described above. Or a salt thereof (for example, hydrochloride, hydrobromide, trifluoroacetate, etc.).

  Reaction formula 2

Formula (VII) [wherein Y ¹ , Y ² , Y ³ , R ¹ , R ² and J ³ represent the same meaning as described above. ], For example, Bioorganic & Med. Chem. Lett. 2009, 19, 1488 and 1492, 2011, 21, 1434, etc. In the formula (X) [wherein R ³ represents C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl, J ⁴ represents a chlorine atom, a bromine atom or an iodine atom. Or a known Grignard reagent represented by the formula (XI): wherein R ³ represents C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl. ] Is reacted with a known lithium reagent represented by formula (XII) [wherein Y ¹ , Y ² , Y ³ , R ¹ , R ^2] , R ³ and J ³ represent the same meaning as above. ] Can be synthesized.

By reacting the compound represented by the formula (XII) thus obtained in the same manner as in the reaction formula 1, the formula (IIb) in which R ⁴ and R ⁵ are hydrogen atoms in the formula (II) [formula Among them, Y ¹ , Y ² , Y ³ , R ¹ , R ² , R ³ and R ⁶ represent the same meaning as described above. Or a salt thereof (for example, hydrochloride, hydrobromide, trifluoroacetate, etc.).

  Reaction formula 3

Formula (VII) [wherein Y ¹ , Y ² , Y ³ , R ¹ , R ² and J ³ represent the same meaning as described above. In the presence of cerium trichloride in accordance with the method described in, for example, Synthesis 2006, page 4143, or the like, or a compound (Synlett) 2007, page 652. In the presence of titanium (IV) tetraisopropoxide, the compound is reacted with a methyl Grignard reagent in the presence of titanium (IV) tetraisopropoxide, wherein Y ¹ , Y ² , Y ³ , R ¹ , R ² and J ³ are as defined above. ] Can be synthesized.

By reacting the compound represented by the formula (XV) thus obtained in the same manner as in Reaction Scheme 1, R ³ and R ⁴ in the formula (II) are methyl groups, and R ⁵ is a hydrogen atom. (Wherein Y ¹ , Y ² , Y ³ , R ¹ , R ² and R ⁶ have the same meaning as above). Or a salt thereof (for example, hydrochloride, hydrobromide, trifluoroacetate, etc.).

  Reaction formula 4

Formula (VII) [wherein Y ¹ , Y ² , Y ³ , R ¹ , R ² and J ³ represent the same meaning as described above. ], For example, in the presence of titanium (IV) tetraisopropoxide and boron trifluoride diethyl ether complex according to the method described in Chemical Communications [Chem. Commun.] 2001, p. By reacting with a Grignard reagent, the formula (XVIII) [wherein Y ¹ , Y ² , Y ³ , R ¹ , R ² and J ³ represent the same meaning as described above. ] Can be synthesized.

By reacting the compound represented by the formula (XVIII) thus obtained in the same manner as in Reaction Scheme 1, R ³ and R ⁴ together in Formula (II) form an ethylene chain. To form a cyclopropyl ring together with the carbon atom to which R ³ and R ⁴ are bonded, and R ⁵ is a hydrogen atom (wherein Y ¹ , Y ² , Y ³ , R ¹ , R ² and R ⁶ represents the same meaning as described above. Or a salt thereof (for example, hydrochloride, hydrobromide, trifluoroacetate, etc.).

  Reaction formula 5

Formula (VII) [wherein Y ¹ , Y ² , Y ³ , R ¹ , R ² and J ³ represent the same meaning as described above. ], For example, according to the method described in Chemical and Pharmaceutical Bulletin [Chem. Pharm. Bull.] 1986, Vol. 34, 4653, etc. R ³ and J ⁴ represent the same meaning as described above. And then hydrolyzed after reaction with a known Grignard reagent represented by the following formula, for example, The Journal of Organic Chemistry [J. Org. Chem.] 1981, 46, 4600, etc. By reacting with diisobutylaluminum hydride according to the method described, and then hydrolyzing, the compound represented by formula (XXI) [wherein Y ¹ , Y ² , Y ³ , R ¹ , R ² , R ³ and J ³ are Means the same. ] Can be synthesized.

Subsequently, the compound represented by the formula (XXI) is represented by the formula (VI) [wherein R ⁶ represents the same meaning as described above, and Q represents a hydrogen atom, a trimethylsilyl group, or the like. ], For example, Tetrahedron Letters [Tetrahedron Lett.] 2012, 53, 4117, Tetrahedron 2005, 61, 2697, etc. By reacting using the reaction conditions, the formula (XXII) [wherein Y ¹ , Y ² , Y ³ , R ¹ , R ² , R ³ and R ⁶ represent the same meaning as described above. ] Can be synthesized.

The compound represented by the formula (XXII) thus obtained is described in, for example, European Journal of Medicinal Chemistry [Eur. J. Med. Chem.] 2009, 44, 4862, etc. According to the method, in the presence of a reducing agent such as sodium cyanoborohydride, the formula (XXIII) [wherein R ⁵ is C ₁ -C ₄ haloalkylthio, —C (O) R ⁹ and C ₁ -C ₄ alkoxycarbonyl. Other than the above, the same meaning as described above is expressed. In the formula (IIe), R ⁴ is a hydrogen atom in the formula (II) [wherein Y ¹ , Y ² , Y ³ , R ¹ , R ² , R ³ , R ⁵ and R ⁶ have the same meaning as described above. The compound represented by this can be obtained.

  Reaction formula 6

Formula (XXIV) [wherein Y ¹ , Y ² , Y ³ and J ³ represent the same meaning as described above. ] According to the method described in, for example, Journal of the Chemical Society Perkin Transactions, 1 [J. Chem. Soc. Perkin Trans. 1] 1979, page 643, etc. Formula (XXV) [wherein R ³ represents the same meaning as described above. And a known nitroalkane derivative represented by the formula (XXVI) [wherein Y ¹ , Y ² , Y ³ , R ³ and J ³ represent the same meaning as described above. ] Can be synthesized.

Next, the compound represented by the formula (XXVI) is reduced with zinc-hydrochloric acid or the like according to the method described in, for example, Synlett 2014, 25, 2891, etc. [Wherein Y ¹ , Y ² , Y ³ , R ³ and J ³ represent the same meaning as described above. ] Can be synthesized.

The compound represented by the formula (XXVII) thus obtained is reacted in the same manner as in the reaction formula 1, so that R ¹ , R ² , R ⁴ and R ⁵ are hydrogen atoms in the formula (II). Formula (IIf) [wherein Y ¹ , Y ² , Y ³ , R ³ and R ⁶ represent the same meaning as described above. Or a salt thereof (for example, hydrochloride, hydrobromide, trifluoroacetate, etc.).

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

  Reaction formula 7

Formula (XXVI) which is a synthetic intermediate of Reaction Formula 6 [wherein Y ¹ , Y ² , Y ³ , R ³ and J ³ represent the same meaning as described above. And a compound represented by the formula (XXX), wherein W represents an oxygen atom, a sulfur atom or —NHO—, and R ^a is C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl, (Z) _m substituted with phenyl (C ₁ -C ₄ ) alkyl and the like. ], For example, tetrahedron [Tetrahedron] 2012, 68, 1521, Tetrahedron Letters 2008, 49, 1244. Page, European Journal of Organic Chemistry [Eur. J. Org. Chem.] 2010, page 5482, etc., by reacting in accordance with the formula (XXXI) [wherein Y ¹ , Y ² , Y ³ , W, R ^a , R ³ and J ³ represent the same meaning as described above. ] Can be synthesized.

Subsequently, the compound represented by the formula (XXXI) is converted into a method described in, for example, Bulletin of the Chemical Society of Japan [Bull. Chem. Soc. Jpn.] 2014, Vol. In accordance with the formula (XXXII) [wherein Y ¹ , Y ² , Y ³ , W, R ^a , R ³ and J ³ represent the same meaning as described above. ] Can be synthesized.

By reacting the compound represented by the formula (XXXII) thus obtained in the same manner as in Reaction Scheme 1, R ¹ is —WR ^a in Formula (II), and R ² , R ⁴ and R Formula (IIg) wherein ⁵ is a hydrogen atom [wherein Y ¹ , Y ² , Y ³ , W, R ^a , R ³ and R ⁶ represent the same meaning as described above. Or a salt thereof (for example, hydrochloride, hydrobromide, trifluoroacetate, etc.).

  Reaction formula 8

Formula (XXXV) [wherein Y ¹ , Y ² , Y ³ , R ³ and J ³ represent the same meaning as described above. The compound represented by the formula (XXXVI) [wherein Y is reacted with potassium phthalimide after being halogenated according to the method described in, for example, International Patent Application Publication (WO 2014/010737)] ¹ , Y ² , Y ³ , R ³ and J ³ represent the same meaning as described above. ] Can be synthesized.

The compound represented by the formula (XXXVI) thus obtained is represented by the formula (VI) [wherein R ⁶ represents the same meaning as described above, Q is a hydrogen atom, a trimethylsilyl group, a -ZnCl group, a -ZnBr Represents a group or a -ZnI group. ] Is reacted in the same manner as in Production Method C, whereby Y ¹ , Y ² , Y ³ , R ³ and R ⁶ have the same meaning as described above. ] Can be synthesized.

Next, the compound represented by the formula (XXXVII) is reduced using a reducing agent such as sodium borohydride according to the method described in, for example, International Patent Application Publication (WO 2013/003740), (XXXVIII) [wherein R ^b represents an ethyl group, 2-methoxyethyl or the like. And a known fluorinating agent represented by the formula (XXXIX) [wherein Y ¹ , Y ² , Y ³ , R ³ and R ⁶ represent the same meaning as described above. ] Can be synthesized.

The compound represented by the formula (XXXIX) thus obtained is converted to toluene, dichloromethane, chloroform, methanol, ethanol, tetrahydrofuran, 1,4-dioxane, water, or any ratio of two or more thereof if necessary. 1 to 4 equivalents of a methylamine aqueous solution, a hydrazine aqueous solution, or a hydrazine monoester with respect to 1 equivalent of a compound represented by the formula (XXXIX) under an inert gas atmosphere such as nitrogen or argon if necessary. In the formula (II), R ¹ represents a fluorine atom, and R ² , R ^4, and R ⁵ are hydrogen atoms by reacting with the hydrate in a temperature range from room temperature to the reflux temperature of the reaction mixture for 1 to 24 hours. Formula (IIh) [wherein Y ¹ , Y ² , Y ³ , R ³ and R ⁶ represent the same meaning as described above. The compound represented by this can be obtained.

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

  Reaction formula 9

Formula (XXXVII), which is a synthetic intermediate of Reaction Formula 8, wherein Y ¹ , Y ² , Y ³ , R ³ and R ⁶ have the same meaning as described above. ], For example, Angewante Chemie International Edition [Angew. Chemie, Int. Ed.] 2011, 50, 2593, Organic Letters [Organic. Lett.] 2007, 9, 5219, The Journal of Organic Chemistry [J. Org. Chem.] 1993, 58, 6509, Tetrahedron 2010, 66, 3499, European Journal of Organic. In accordance with the method described in Chemistry [Eur. J. Org. Chem.] 2007, 266, etc., presence of strong base such as potassium tert-butoxide, sodium hexamethyldisilazide, lithium diisopropylamide, alkyllithium, etc. under the formula (XL) [wherein, R ^c is a hydrogen atom, a halogen atom, C ₁ -C ₅ alkyl, C ₁ -C ₅ halo Alkyl or C ₁ -C ₄ alkoxy like, J ⁴ are as defined above. ] Is reacted with a compound represented by the formula (XLI) [wherein Y ¹ , Y ² , Y ³ , R ³ , R ⁶ and R ^c represent the same meaning as described above. ] Can be synthesized.

The compound represented by the formula (XLI) thus obtained is reacted with a methylamine aqueous solution, a hydrazine aqueous solution, hydrazine monohydrate, or the like in the same manner as in the reaction formula 8 to obtain R in the formula (II). ¹ and R ² together form C ₁ -C ₆ alkylidene, C ₁ -C ₆ haloalkylidene, or C ₁ -C ₄ alkoxy (C ₁ -C ₂ ) alkylidene, and R ⁴ and R ⁵ are hydrogen Formula (IIi) which is an atom [wherein Y ¹ , Y ² , Y ³ , R ³ , R ⁶ and R ^c represent the same meaning as described above. The compound represented by this can be obtained.

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

  Reaction formula 10

Formula (XLII) [wherein Y ¹ , Y ² , Y ³ and J ³ represent the same meaning as described above, and R ¹ represents C ₁ -C ₆ alkyl and the like. The compound represented by the formula (XLIII) is reacted with trimethylsulfoxonium iodide or the like according to a method described in, for example, Synthetic Communications [Synth. Commun.] 2003, 33, 2135. [Wherein Y ¹ , Y ² , Y ³ , R ¹ and J ³ represent the same meaning as described above.] ] Can be synthesized.

Next, the compound represented by the formula (XLIII) is reacted with potassium phthalimide according to the method described in, for example, International Patent Application Publication (WO 2006/136821), for example, to formula (XLIV) [wherein Y ¹ , Y ² , Y ³ , R ¹ and J ³ represent the same meaning as described above. ], Then, for example, according to the method described in International Patent Application Publication (WO 2009/123855) and the like, the formula (XXXVIII) [wherein R ^b represents the same meaning as described above. ] Is reacted with a known fluorinating agent represented by the formula (XLV) [wherein Y ¹ , Y ² , Y ³ , R ¹ and J ³ represent the same meaning as described above. ] Can be synthesized.

The compound represented by the formula (XLV) thus obtained is represented by the formula (VI) [wherein R ⁶ represents the same meaning as described above, Q is a hydrogen atom, a trimethylsilyl group, a —ZnCl group, a —ZnBr Represents a group or a -ZnI group. ] Is substituted with the substituted acetylene represented by the formula (XLVI) [wherein Y ¹ , Y ² , Y ³ , R ¹ and R ⁶ have the same meaning as described above. ] Can be synthesized.

Next, by reacting the compound represented by the formula (XLVI) with an aqueous methylamine solution, an aqueous hydrazine solution or hydrazine monohydrate in the same manner as in the reaction formula 8, R ² in the formula (II) is a fluorine atom, Formula (IIj) wherein R ³ , R ⁴ and R ⁵ are hydrogen atoms [wherein Y ¹ , Y ² , Y ³ , R ¹ and R ⁶ represent the same meaning as described above. The compound represented by this can be obtained.

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

  The compound represented by Formula (VIII) used in Reaction Formula 1 to Reaction Formula 5 can be synthesized, for example, as in the following Reaction Formula 11 to Reaction Formula 15.

  Reaction formula 11

Formula (XLVII) [wherein Y ¹ , Y ² , Y ³ and J ³ represent the same meaning as described above, and J ⁵ represents a halogen atom. ], For example, The Journal of Organic Chemistry [J. Org. Chem.] 2008, 73, 1643, Bioorganic & Medicinal Chemistry Letters [Bioorganic & Med. Chem. Lett.] 2009, Vol. 19, p. 4484, etc., a known formula (XLVIII) [wherein R ^d represents a C ₁ -C ₄ alkyl group. And a cyanoacetate represented by the formula (XLIX) [wherein Y ¹ , Y ² , Y ³ , J ³ and R ^d represent the same meaning as described above. ] Can be synthesized.

Next, the compound represented by the formula (XLIX) is described in, for example, Journal of Medicinal Chemistry [J. Med. Chem.] 2005, 48, 2167, Synthesis 2010, 3332, etc. In the formula (VII), R ¹ and R ² are hydrogen atoms in the formula (VIIa) [wherein Y ¹ , Y ² , Y ³ and J ³ are the same as the above Represents meaning. ] Can be synthesized.

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

  Reaction formula 12

Formula (VIIa) [wherein Y ¹ , Y ² , Y ³ and J ³ represent the same meaning as described above. ], For example, according to the method described in Journal of Heterocyclic Chemistry [J. Heterocyclic Chem.] 1987, Vol. 24, page 1061, etc. , J ³ represents the same meaning as described above, and R ¹ represents a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ haloalkyl group, a phenyl (C ₁ -C ₄ ) alkyl group substituted by (Z) _m , etc. Represent. And a compound represented by formula (VIIb) in which R ² is a hydrogen atom in formula (VII): wherein Y ¹ , Y ² , Y ³ , R ¹ and J ³ are the same as above Represents meaning. ] Can be synthesized.

  Reaction formula 13

Formula (XLVII) [wherein Y ¹ , Y ² , Y ³ , J ³ and J ⁵ represent the same meaning as described above. ], For example, Journal of Heterocyclic Chemistry [J. Heterocyclic Chem.] 1987, 24, 1061; The Journal of Organic Chemistry [J. Org. Chem. In accordance with the method described in 2005, 70, 10186, etc., the formula (LI) [wherein R ¹ represents the same meaning as described above except for a halogen atom. And a compound represented by formula (VIIb) in which R ² is a hydrogen atom in formula (VII): wherein Y ¹ , Y ² , Y ³ , R ¹ and J ³ are the same as above Represents meaning. ] Can also be synthesized.

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

  Reaction formula 14

Formula (VIIb) [wherein Y ¹ , Y ² , Y ³ , R ¹ and J ³ represent the same meaning as described above. The compound represented by the formula (LII) according to the method described in, for example, European Journal of Medicinal Chemistry [Eur. J. Med. Chem.] 2004, 39, 993, etc. [Wherein J ³ represents the same meaning as described above, and R ² represents a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ haloalkyl group, or the like. ] Is reacted with a compound represented by formula (VII) [wherein Y ¹ , Y ² , Y ³ , R ¹ , R ² and J ³ represent the same meaning as described above. ] Can be synthesized.

  Reaction formula 15

Formula (VIIa) [wherein Y ¹ , Y ² , Y ³ and J ³ represent the same meaning as described above. In accordance with the method described in, for example, The Journal of Organic Chemistry [J. Org. Chem.] 1998, 63, 8052, a strong compound such as tert-butyllithium is used. By reacting with a fluorinating agent such as N-fluorobenzenesulfonic acid imide in the presence of a base, R ¹ and R ² are fluorine atoms in formula (VII) [wherein Y ¹ , Y ² , Y ³ and J ³ have the same meaning as above. ] Can be synthesized.

  Reaction formula 16

Formula (VIIa) [wherein Y ¹ , Y ² , Y ³ and J ³ represent the same meaning as described above. ], For example, according to the method described in Journal of Medicinal Chemistry [J. Med. Chem.] 2010, Vol. 53, p. J ⁵ represents the same meaning as described above. In the formula (VII), R ¹ and R ² are combined together to form an ethylene chain, thereby forming a cyclopropyl ring together with the carbon atom to which R ¹ and R ² are bonded. [Wherein Y ¹ , Y ² , Y ³ and J ³ represent the same meaning as described above.] ] Can be synthesized.

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

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

  Specific examples of the alkynylpyridine-substituted amide compound represented by the formula (I) included in the present invention that can be produced using these methods include the following structural formulas [I] -1 to [I] -48. The compound represented by these is mentioned. However, the compounds represented by the structural formulas [I] -1 to [I] -48 are for illustrative purposes, and the alkynylpyridine-substituted amide compounds included in the present invention are limited to these. is not.

Here, it is represented by Y ¹ , Y ² , Y ³ , R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ in the structural formulas [I] -1 to [I] -48. Examples of specific combinations of substituents include, for example, combinations shown in Table 2. However, the combinations in Table 2 are for illustrative purposes, and Y ¹ , Y ² , Y ³ , R ¹ , R ² , R ³ , R ⁴ , of the alkynylpyridine-substituted amide compounds included in the present invention, Specific combinations of substituents represented by R ⁵ and R ⁶ are not limited to these.

In the table, the description of Et represents an ethyl group. Similarly, n-Pr represents a normal propyl group, i-Pr and Pr-i represent an isopropyl group, c-Pr represents a cyclopropyl group, and Bu-- s is a sec-butyl group, c-Bu is a cyclobutyl group, t-Bu and Bu-t are tert-butyl groups, c-Pen is a cyclopentyl group, c-Hex is a cyclohexyl group, Ph is a phenyl group 1-Naph represents a 1-naphthyl group, 2-Naph represents a 2-naphthyl group,
In the table, the aromatic heterocycles represented by D-1-1a to D-26-1b each represent the following structure,

The number representing the substitution position of the substituent (Z) _n corresponds to the position of the number described in the above structural formula. For example, in the table, “(D-23-2b) -6-F” The description represents “6-fluoropyridin-3-yl group”,
In the table, the aromatic heterocycles represented by D-31-a to D-35-c each represent the following structure,

  In the table, T-1 to T-14 each represent the following structure.

  In the table, substituent R¹And substituent R³The notation of (R) and (S) in the column of¹Or R³Represents the ratio of (R) -isomer or (S) -isomer in the mixing ratio of the optical isomer of the carbon atom to which
  In the table, substituent R¹And R²The description of (E) and (Z) in the column of¹And R²Represents a ratio of (E) -isomer or (Z) -isomer of 90% or more in the mixing ratio of the geometrical isomers of alkylidene groups formed together.
Table 2
―――――――――――――――――――――――――――――――――――――――
R^Five       R^Three      R^Four       R¹       R²       Y¹      Y²         R⁶          Y^Three
―――――――――――――――――――――――――――――――――――――――
H H H H H Cl H Ph-2-F H
H H H H H Cl H Ph-3-F H
CH_Three      H H H H Cl H Ph-3-F H
Et H H H H Cl H Ph-3-F H
i-Pr H H H H Cl H Ph-3-F H
c-Pr H H H H Cl H Ph-3-F H
c-Bu H H H H Cl H Ph-3-F H
CH₂CHF₂  H H H H Cl H Ph-3-F H
CH₂OCH_Three  H H H H Cl H Ph-3-F H
CH₂OEt H H H H Cl H Ph-3-F H
CH₂OC (O) CH_Three  H H H H Cl H Ph-3-F H
CH₂OC (O) OCH_Three H H H H Cl H Ph-3-F H
CH₂SCH_Three      H H H H Cl H Ph-3-F H
CH₂CN H H H H Cl H Ph-3-F H
CH₂C (O) OCH_Three  H H H H Cl H Ph-3-F H
CH₂C (O) NH₂   H H H H Cl H Ph-3-F H
CH₂C (S) NH₂   H H H H Cl H Ph-3-F H
CH₂CH = CH₂    H H H H Cl H Ph-3-F H
CH₂C≡CH H H H H Cl H Ph-3-F H
OCH_Three     H H H H Cl H Ph-3-F H
OEt H H H H Cl H Ph-3-F H
SCCl_Three    H H H H Cl H Ph-3-F H
C (O) CH_Three  H H H H Cl H Ph-3-F H
C (O) OCH_Three H H H H Cl H Ph-3-F H
H H H H H Cl H Ph-4-F H
H H H H H Cl H Ph-2-Cl H
H H H H H Cl H Ph-3-Cl H
H H H H H Cl H Ph-4-Cl H
H H H H H Cl H Ph-2-CH_Three       H
H H H H H Cl H Ph-3-CH_Three       H
H H H H H Cl H Ph-4-CH_Three       H
H H H H H Cl H Ph-2-CF_Three       H
H H H H H Cl H Ph-3-CF_Three       H
H H H H H Cl H Ph-4-CF_Three       H
H H H H H Cl H Ph-2-OCH_Three      H
H H H H H Cl H Ph-3-OCH_Three      H
H H H H H Cl H Ph-4-OCH_Three      H
H H H H H Cl H Ph-4-OCHF₂     H
H H H H H Cl H Ph-4-OCF_Three      H
H H H H H Cl H Ph-2,4-F₂      H
H H H H H Cl H Ph-3,4-F₂      H
H H H H H Cl H Ph-3-Cl-4-F H
H H H H H Cl H Ph-2-F-4-Cl H
H H H H H Cl H Ph-3-F-4-Cl H
H H H H H Cl H Ph-3,4-Cl₂      H
H H H H H Cl H Ph-2-F-4-CH_Three     H
H H H H H Cl H Ph-2-CH_Three-4-Cl H
H H H H H Cl H Ph-2-F-4-CF_Three     H
H H H H H Cl H Ph-3-F-4-CF_Three     H
H H H H H Cl H Ph-2-F-4-OCF_Three    H
H H H H H Cl H Ph-3-F-4-OCF_Three    H
H H H H H Cl H T-15 H
H H H H H Cl H Ph-2,4,5-F_Three     H
H H H H H Cl H Ph-2,4,6-F_Three     H
H H H H H Cl H Ph-3,4,5-F_Three     H
H H H H H Cl H D-1-2a H
H H H H H Cl H (D-1-2b) -2-CH_Three    H
H H H H H Cl H (D-2-1b) -5-F H
H H H H H Cl H (D-8-2b) -2-CH_Three    H
H H H H H Cl H (D-23-2b) -6-F H
H H H H H Cl H (D-23-2b) -6-Cl H
H H H H H Cl CH_Three      Ph-2-F H
H H H H H Cl CH_Three      Ph-3-F H
H H H H H Cl CH_Three      Ph-4-F H
H H H H H Br H Ph-2-F H
H H H H H Br H Ph-3-F H
H H H H H Br H Ph-4-F H
H H H H H CH_Three     H Ph-2-F H
H H H H H CH_Three     H Ph-3-F H
H H H H H CH_Three     H Ph-4-F H
H H H H H CH_Three     CH_Three      Ph-2-F H
H H H H H CH_Three     CH_Three      Ph-3-F H
H H H H H CH_Three     CH_Three      Ph-4-F H
H H H H H CF_Three     H Ph-2-F H
H H H H H CF_Three     H Ph-3-F H
H H H H H CF_Three     H Ph-4-F H
H H H H H OCH_Three     H Ph-2-F H
H H H H H OCH_Three     H Ph-3-F H
H H H H H OCH_Three     H Ph-4-F H
H H H H H OCHF₂    H Ph-2-F H
H H H H H OCHF₂    H Ph-3-F H
H H H H H OCHF₂    H Ph-4-F H
H H H H H SCH_Three     H Ph-2-F H
H H H H H SCH_Three     H Ph-3-F H
H H H H H SCH_Three     H Ph-4-F H
H H H F H Cl H Ph-2-F H
H H H F H Cl H Ph-3-F H
H H H F H Cl H Ph-4-F H
H H H F H Cl H Ph-2-Cl H
H H H F H Cl H Ph-3-Cl H
H H H F H Cl H Ph-4-Cl H
H H H F H Cl H Ph-2-CH_Three       H
H H H F H Cl H Ph-3-CH_Three       H
H H H F H Cl H Ph-4-CH_Three       H
H H H F H Cl H Ph-2-CF_Three       H
H H H F H Cl H Ph-3-CF_Three       H
H H H F H Cl H Ph-4-CF_Three       H
H H H F H Cl H Ph-2-OCH_Three      H
H H H F H Cl H Ph-3-OCH_Three      H
H H H F H Cl H Ph-4-OCH_Three      H
H H H F H Cl H Ph-4-OCHF₂     H
H H H F H Cl H Ph-4-OCF_Three      H
H H H F H Cl H Ph-2,4-F₂      H
H H H F H Cl H Ph-3,4-F₂      H
H H H F H Cl H Ph-3-Cl-4-F H
H H H F H Cl H Ph-2-F-4-Cl H
H H H F H Cl H Ph-3-F-4-Cl H
H H H F H Cl H Ph-3,4-Cl₂      H
H H H F H Cl H Ph-2-F-4-CH_Three     H
H H H F H Cl H Ph-2-CH_Three-4-Cl H
H H H F H Cl H Ph-2-F-4-CF_Three     H
H H H F H Cl H Ph-3-F-4-CF_Three     H
H H H F H Cl H Ph-2-F-4-OCF_Three    H
H H H F H Cl H Ph-3-F-4-OCF_Three    H
H H H F H Cl H T-15 H
H H H F H Cl H Ph-2,4,5-F_Three     H
H H H F H Cl H Ph-2,4,6-F_Three     H
H H H F H Cl H Ph-3,4,5-F_Three     H
H H H F H Cl H D-1-2a H
H H H F H Cl H (D-1-2b) -2-CH_Three    H
H H H F H Cl H (D-2-1b) -5-F H
H H H F H Cl H (D-8-2b) -2-CH_Three    H
H H H F H Cl H (D-23-2b) -6-F H
H H H F H Cl H (D-23-2b) -6-Cl H
H H H F F Cl H Ph-2-F H
H H H F F Cl H Ph-3-F H
H H H F F Cl H Ph-4-F H
H H H F F Cl H Ph-2-Cl H
H H H F F Cl H Ph-3-Cl H
H H H F F Cl H Ph-4-Cl H
H H H F F Cl H Ph-4-Br H
H H H F F Cl H Ph-2-CH_Three       H
H H H F F Cl H Ph-3-CH_Three       H
H H H F F Cl H Ph-4-CH_Three       H
H H H F F Cl H Ph-4-Bu-t H
H H H F F Cl H Ph-2-CF_Three       H
H H H F F Cl H Ph-3-CF_Three       H
H H H F F Cl H Ph-4-CF_Three       H
H H H F F Cl H Ph-2-OCH_Three      H
H H H F F Cl H Ph-3-OCH_Three      H
H H H F F Cl H Ph-4-OCH_Three      H
H H H F F Cl H Ph-2-OCHF₂     H
H H H F F Cl H Ph-3-OCHF₂     H
H H H F F Cl H Ph-4-OCHF₂     H
H H H F F Cl H Ph-2-OCF_Three      H
H H H F F Cl H Ph-3-OCF_Three      H
H H H F F Cl H Ph-4-OCF_Three      H
H H H F F Cl H Ph-2-SCH_Three      H
H H H F F Cl H Ph-3-SCH_Three      H
H H H F F Cl H Ph-4-SCH_Three      H
H H H F F Cl H Ph-2-S (O) CH_Three    H
H H H F F Cl H Ph-3-S (O) CH_Three    H
H H H F F Cl H Ph-4-S (O) CH_Three    H
H H H F F Cl H Ph-2-SO₂CH_Three     H
H H H F F Cl H Ph-3-SO₂CH_Three     H
H H H F F Cl H Ph-4-SO₂CH_Three     H
H H H F F Cl H Ph-2-SCHF₂     H
H H H F F Cl H Ph-3-SCHF₂     H
H H H F F Cl H Ph-3-SO₂CHF₂    H
H H H F F Cl H Ph-4-SCHF₂     H
H H H F F Cl H Ph-4-SO₂CHF₂    H
H H H F F Cl H Ph-2-SCF_Three      H
H H H F F Cl H Ph-3-SCF_Three      H
H H H F F Cl H Ph-3-SO₂CF_Three     H
H H H F F Cl H Ph-4-SCF_Three      H
H H H F F Cl H Ph-4-S (O) CF_Three    H
H H H F F Cl H Ph-4-SO₂CF_Three     H
H H H F F Cl H Ph-4-SF_Five       H
H H H F F Cl H Ph-2-NO₂       H
H H H F F Cl H Ph-3-NO₂       H
H H H F F Cl H Ph-4-NO₂       H
H H H F F Cl H Ph-2-CN H
H H H F F Cl H Ph-3-CN H
H H H F F Cl H Ph-4-CN H
H H H F F Cl H Ph-4- (D-31-a) H
H H H F F Cl H Ph-4- (D-32-a) H
H H H F F Cl H Ph-4- (D-33-b) H
H H H F F Cl H Ph-2,3-F₂      H
H H H F F Cl H Ph-2,4-F₂      H
H H H F F Cl H Ph-2,5-F₂      H
H H H F F Cl H Ph-2,6-F₂      H
H H H F F Cl H Ph-3,4-F₂      H
H H H F F Cl H Ph-3,5-F₂      H
H H H F F Cl H Ph-2-Cl-4-F H
H H H F F Cl H Ph-2-F-3-Cl H
H H H F F Cl H Ph-3-Cl-4-F H
H H H F F Cl H Ph-2-F-4-Cl H
H H H F F Cl H Ph-3-F-4-Cl H
H H H F F Cl H Ph-2,4-Cl₂      H
H H H F F Cl H Ph-3,4-Cl₂      H
H H H F F Cl H Ph-2-F-4-Br H
H H H F F Cl H Ph-3-F-4-Br H
H H H F F Cl H Ph-2-CH_Three-3-F H
H H H F F Cl H Ph-2-CH_Three-4-F H
H H H F F Cl H Ph-2-F-3-CH_Three     H
H H H F F Cl H Ph-3-CH_Three-4-F H
H H H F F Cl H Ph-2-F-4-CH_Three     H
H H H F F Cl H Ph-3-F-4-CH_Three     H
H H H F F Cl H Ph-2-CH_Three-4-Cl H
H H H F F Cl H Ph-3-CH_Three-4-Cl H
H H H F F Cl H Ph-3-Cl-4-CH_Three    H
H H H F F Cl H Ph-2-CF_Three-3-F H
H H H F F Cl H Ph-2-CF_Three-4-F H
H H H F F Cl H Ph-2-F-3-CF_Three     H
H H H F F Cl H Ph-3-CF_Three-4-F H
H H H F F Cl H Ph-2-F-4-CF_Three     H
H H H F F Cl H Ph-3-F-4-CF_Three     H
H H H F F Cl H Ph-2-F-5-CF_Three     H
H H H F F Cl H Ph-3-F-5-CF_Three     H
H H H F F Cl H Ph-2-CF_Three-4-Cl H
H H H F F Cl H Ph-3-CF_Three-4-Cl H
H H H F F Cl H Ph-3-Cl-4-CF_Three    H
H H H F F Cl H Ph-3-OCH_Three-4-F H
H H H F F Cl H Ph-2-F-4-OCH_Three    H
H H H F F Cl H Ph-3-F-4-OCH_Three    H
H H H F F Cl H Ph-3-OCH_Three-4-Cl H
H H H F F Cl H Ph-3-Cl-4-OCH_Three    H
H H H F F Cl H Ph-2-F-4-OCHF₂    H
H H H F F Cl H Ph-3-F-4-OCHF₂    H
H H H F F Cl H Ph-3-Cl-4-OCHF₂   H
H H H F F Cl H Ph-2-F-4-OCF_Three    H
H H H F F Cl H Ph-3-F-4-OCF_Three    H
H H H F F Cl H Ph-2-Cl-4-OCF_Three    H
H H H F F Cl H T-15 H
H H H F F Cl H T-19 H
H H H F F Cl H T-20 H
H H H F F Cl H T-21 H
H H H F F Cl H Ph-2-F-4-CN H
H H H F F Cl H Ph-3-F-4-CN H
H H H F F Cl H Ph-3-Cl-4-CN H
H H H F F Cl H Ph-2-F-4- (D-32-b) H
H H H F F Cl H Ph-3-F-4- (D-32-b) H
H H H F F Cl H Ph-3-F-4- (D-33-a) H
H H H F F Cl H Ph-3-F-4- (D-33-b) H
H H H F F Cl H Ph-2-F-4- (D-35-a) H
H H H F F Cl H Ph-3-F-4- (D-35-a) H
H H H F F Cl H Ph-3-F-4- (D-35-b) H
H H H F F Cl H Ph-3-F-4- (D-35-c) H
H H H F F Cl H Ph-2,3,4-F_Three     H
H H H F F Cl H Ph-2,3,5-F_Three     H
H H H F F Cl H Ph-2,3,6-F_Three     H
H H H F F Cl H Ph-2,4,5-F_Three     H
H H H F F Cl H Ph-2,4,6-F_Three     H
H H H F F Cl H Ph-3,4,5-F_Three     H
H H H F F Cl H Ph-2,3-F₂-4-Cl H
H H H F F Cl H Ph-2,5-F₂-4-Cl H
H H H F F Cl H Ph-2,6-F₂-4-Cl H
H H H F F Cl H Ph-3,5-F₂-4-Cl H
H H H F F Cl H Ph-2-F-4-Cl-5-CH_Three  H
H H H F F Cl H Ph-2,5-F₂-4-CF_Three   H
H H H F F Cl H Ph-2,3-F₂-4-OCH_Three   H
H H H F F Cl H Ph-2,5-F₂-4-OCH_Three   H
H H H F F Cl H Ph-2,6-F₂-4-OCH_Three   H
H H H F F Cl H Ph-3,5-F₂-4-OCH_Three   H
H H H F F Cl H T-16 H
H H H F F Cl H T-17 H
H H H F F Cl H T-18 H
H H H F F Cl H 1-Naph H
H H H F F Cl H 2-Naph H
H H H F F Cl H D-1-1a H
H H H F F Cl H (D-1-1b) -5-F H
H H H F F Cl H (D-1-1b) -4-Br H
H H H F F Cl H (D-1-1b) -5-Br H
H H H F F Cl H (D-1-1b) -3-CH_Three    H
H H H F F Cl H (D-1-1b) -4-CH_Three    H
H H H F F Cl H (D-1-1b) -5-CH_Three    H
H H H F F Cl H (D-1-1b) -5-CF_Three    H
H H H F F Cl H D-1-2a H
H H H F F Cl H (D-1-2b) -2-F H
H H H F F Cl H (D-1-2b) -2-CH_Three    H
H H H F F Cl H (D-1-2b) -4-CH_Three    H
H H H F F Cl H (D-1-2b) -5-CH_Three    H
H H H F F Cl H D-2-1a H
H H H F F Cl H (D-2-1b) -3-F H
H H H F F Cl H (D-2-1b) -4-F H
H H H F F Cl H (D-2-1b) -5-F H
H H H F F Cl H (D-2-1b) -4-Cl H
H H H F F Cl H (D-2-1b) -5-Cl H
H H H F F Cl H (D-2-1b) -3-CH_Three    H
H H H F F Cl H (D-2-1b) -4-CH_Three    H
H H H F F Cl H (D-2-1b) -5-CH_Three    H
H H H F F Cl H (D-2-1b) -5-CHF₂   H
H H H F F Cl H (D-2-1b) -5-CF_Three    H
H H H F F Cl H (D-2-1b) -3-OCH_Three   H
H H H F F Cl H (D-2-1b) -4-OCH_Three   H
H H H F F Cl H (D-2-1b) -5-OCH_Three   H
H H H F F Cl H (D-2-1b) -4-OCF_Three   H
H H H F F Cl H (D-2-1b) -5-OCF_Three   H
H H H F F Cl H (D-2-1b) -4-CN H
H H H F F Cl H (D-2-1b) -5-CN H
H H H F F Cl H (D-2-1b) -3-CH_Three-5-Cl H
H H H F F Cl H (D-2-1b) -3-CH_Three-5-CN H
H H H F F Cl H D-2-2a H
H H H F F Cl H (D-2-2b) -2-F H
H H H F F Cl H (D-2-2b) -4-F H
H H H F F Cl H (D-2-2b) -5-F H
H H H F F Cl H (D-2-2b) -5-Cl H
H H H F F Cl H (D-2-2b) -2-CH_Three    H
H H H F F Cl H (D-2-2b) -4-CH_Three    H
H H H F F Cl H (D-2-2b) -5-CH_Three    H
H H H F F Cl H (D-2-2b) -5-CHF₂   H
H H H F F Cl H (D-2-2b) -2-CF_Three    H
H H H F F Cl H (D-2-2b) -2-OCH_Three   H
H H H F F Cl H (D-2-2b) -4-OCH_Three   H
H H H F F Cl H (D-2-2b) -5-OCH_Three   H
H H H F F Cl H (D-2-2b) -5-OCF_Three   H
H H H F F Cl H (D-2-2b) -5-CN H
H H H F F Cl H (D-2-2b) -2,5-Cl₂   H
H H H F F Cl H (D-2-2b) -2-CH_Three-5-F H
H H H F F Cl H (D-2-2b) -2-CH_Three-5-Cl H
H H H F F Cl H (D-2-2b) -2-CH_Three-5-CN H
H H H F F Cl H (D-6-1a) -1-CH_Three    H
H H H F F Cl H (D-7-1b) -4-CH_Three    H
H H H F F Cl H (D-7-1b) -4-CF_Three    H
H H H F F Cl H D-8-1a H
H H H F F Cl H (D-8-1b) -4-F H
H H H F F Cl H (D-8-1b) -4-CH_Three    H
H H H F F Cl H (D-8-1b) -5-CH_Three    H
H H H F F Cl H (D-8-1b) -4-CF_Three    H
H H H F F Cl H D-8-2a H
H H H F F Cl H (D-8-2b) -2-CH_Three    H
H H H F F Cl H (D-8-2b) -5-CH_Three    H
H H H F F Cl H D-8-3a H
H H H F F Cl H (D-8-3b) -2-CH_Three    H
H H H F F Cl H D-23-1a H
H H H F F Cl H (D-23-1b) -3-F H
H H H F F Cl H (D-23-1b) -3-Cl H
H H H F F Cl H (D-23-1b) -3-CH_Three   H
H H H F F Cl H (D-23-1b) -4-Cl H
H H H F F Cl H (D-23-1b) -4-CH_Three   H
H H H F F Cl H (D-23-1b) -4-CF_Three   H
H H H F F Cl H (D-23-1b) -5-F H
H H H F F Cl H (D-23-1b) -5-CH_Three   H
H H H F F Cl H (D-23-1b) -5-CF_Three   H
H H H F F Cl H (D-23-1b) -5-OCF_Three   H
H H H F F Cl H (D-23-1b) -6-F H
H H H F F Cl H (D-23-1b) -6-Cl H
H H H F F Cl H (D-23-1b) -6-CH_Three   H
H H H F F Cl H (D-23-1b) -6-CF_Three   H
H H H F F Cl H (D-23-1b) -6-OCH_Three   H
H H H F F Cl H (D-23-1b) -4,5-F₂   H
H H H F F Cl H (D-23-1b) -3-Cl-5-F H
H H H F F Cl H (D-23-1b) -3,5-Cl₂  H
H H H F F Cl H (D-23-1b) -4,5-Cl₂  H
H H H F F Cl H (D-23-1b) -3-F-5-CF_Three H
H H H F F Cl H (D-23-1b) -3-Cl-5-CF_Three H
H H H F F Cl H D-23-2a H
H H H F F Cl H (D-23-2b) -2-F H
H H H F F Cl H (D-23-2b) -2-Cl H
H H H F F Cl H (D-23-2b) -2-CH_Three   H
H H H F F Cl H (D-23-2b) -4-Cl H
H H H F F Cl H (D-23-2b) -4-CH_Three   H
H H H F F Cl H (D-23-2b) -5-F H
H H H F F Cl H (D-23-2b) -5-Cl H
H H H F F Cl H (D-23-2b) -5-CH_Three   H
H H H F F Cl H (D-23-2b) -5-OCH_Three   H
H H H F F Cl H (D-23-2b) -6-F H
H H H F F Cl H (D-23-2b) -6-Cl H
H H H F F Cl H (D-23-2b) -6-CH_Three   H
H H H F F Cl H (D-23-2b) -6-CF_Three   H
H H H F F Cl H (D-23-2b) -6-OCH_Three   H
H H H F F Cl H (D-23-2b) -6-CN H
H H H F F Cl H (D-23-2b) -4,6-F₂   H
H H H F F Cl H (D-23-2b) -4-F-6-Cl H
H H H F F Cl H (D-23-2b) -5-F-5-CH_Three H
H H H F F Cl H (D-23-2b) -5-F-5-CF_Three H
H H H F F Cl H (D-23-2b) -4-F-6-OCH_Three H
H H H F F Cl H (D-23-2b) -5-F-6-OCH_Three H
H H H F F Cl H (D-23-2b) -5-F-6-OCF_Three H
H H H F F Cl H D-23-3a H
H H H F F Cl H (D-23-3b) -2-F H
H H H F F Cl H (D-23-3b) -2-Cl H
H H H F F Cl H (D-23-3b) -2-CH_Three   H
H H H F F Cl H (D-23-3b) -2-CF_Three   H
H H H F F Cl H (D-23-3b) -2-OCH_Three   H
H H H F F Cl H (D-23-3b) -3-F H
H H H F F Cl H (D-23-3b) -3-CH_Three   H
H H H F F Cl H D-24-1a H
H H H F F Cl H (D-24-1b) -6-CH_Three   H
H H H F F Cl H (D-24-1b) -6-OCH_Three   H
H H H F F Cl H D-25-1a H
H H H F F Cl H (D-25-1b) -4-F H
H H H F F Cl H (D-25-1b) -4-CF_Three   H
H H H F F Cl H (D-25-1b) -4-OCH_Three   H
H H H F F Cl H D-25-2a H
H H H F F Cl H (D-25-2b) -2-Cl H
H H H F F Cl H D-25-3a H
H H H F F Cl H (D-25-3b) -2-Cl H
H H H F F Cl H (D-25-3b) -2-CH_Three   H
H H H F F Cl H (D-25-3b) -2-OCH_Three   H
H H H F F Cl H D-26-1a H
H H H F F Cl H (D-26-1b) -5-CH_Three   H
H H H F F Cl H (D-26-1b) -6-Cl H
H H H F F Br H Ph-2-F H
H H H F F Br H Ph-3-F H
H H H F F Br H Ph-4-F H
H H H F F CH_Three     H Ph-2-F H
H H H F F CH_Three     H Ph-3-F H
H H H F F CH_Three     H Ph-4-F H
H H H F F OCH_Three     H Ph-2-F H
H H H F F OCH_Three     H Ph-3-F H
H H H F F OCH_Three     H Ph-4-F H
H H H CH_Three      H Cl H Ph-2-F H
H H H CH_Three      H Cl H Ph-3-F H
H H H CH_Three      H Cl H Ph-4-F H
H H H CH_Three      H Cl H Ph-2-Cl H
H H H CH_Three      H Cl H Ph-3-Cl H
H H H CH_Three      H Cl H Ph-4-Cl H
H H H CH_Three      H Cl H Ph-2-CH_Three       H
H H H CH_Three      H Cl H Ph-3-CH_Three       H
H H H CH_Three      H Cl H Ph-4-CH_Three       H
H H H CH_Three      H Cl H Ph-2-CF_Three       H
H H H CH_Three      H Cl H Ph-3-CF_Three       H
H H H CH_Three      H Cl H Ph-4-CF_Three       H
H H H CH_Three      H Cl H Ph-2-OCH_Three      H
H H H CH_Three      H Cl H Ph-3-OCH_Three      H
H H H CH_Three      H Cl H Ph-4-OCH_Three      H
H H H CH_Three      H Cl H Ph-4-OCHF₂     H
H H H CH_Three      H Cl H Ph-4-OCF_Three      H
H H H CH_Three      H Cl H Ph-2,4-F₂      H
H H H CH_Three      H Cl H Ph-3,4-F₂      H
H H H CH_Three      H Cl H Ph-3-Cl-4-F H
H H H CH_Three      H Cl H Ph-2-F-4-Cl H
H H H CH_Three      H Cl H Ph-3-F-4-Cl H
H H H CH_Three      H Cl H Ph-3,4-Cl₂      H
H H H CH_Three      H Cl H Ph-2-F-4-CH_Three     H
H H H CH_Three      H Cl H Ph-2-CH_Three-4-Cl H
H H H CH_Three      H Cl H Ph-2-F-4-CF_Three     H
H H H CH_Three      H Cl H Ph-3-F-4-CF_Three     H
H H H CH_Three      H Cl H Ph-2-F-4-OCF_Three    H
H H H CH_Three      H Cl H Ph-3-F-4-OCF_Three    H
H H H CH_Three      H Cl H T-15 H
H H H CH_Three      H Cl H Ph-2,4,5-F_Three     H
H H H CH_Three      H Cl H Ph-2,4,6-F_Three     H
H H H CH_Three      H Cl H Ph-3,4,5-F_Three     H
H H H CH_Three      H Cl H D-1-2a H
H H H CH_Three      H Cl H (D-1-2b) -2-CH_Three    H
H H H CH_Three      H Cl H (D-2-1b) -5-F H
H H H CH_Three      H Cl H (D-8-2b) -2-CH_Three    H
H H H CH_Three      H Cl H (D-23-2b) -6-F H
H H H CH_Three      H Cl H (D-23-2b) -6-Cl H
H H H CH_Three      F Cl H Ph-2-F H
H H H CH_Three      F Cl H Ph-3-F H
H H H CH_Three      F Cl H Ph-4-F H
H H H CH_Three      F Cl H Ph-2-Cl H
H H H CH_Three      F Cl H Ph-3-Cl H
H H H CH_Three      F Cl H Ph-4-Cl H
H H H CH_Three      F Cl H Ph-2-CH_Three       H
H H H CH_Three      F Cl H Ph-3-CH_Three       H
H H H CH_Three      F Cl H Ph-4-CH_Three       H
H H H CH_Three      F Cl H Ph-2-CF_Three       H
H H H CH_Three      F Cl H Ph-3-CF_Three       H
H H H CH_Three      F Cl H Ph-4-CF_Three       H
H H H CH_Three      F Cl H Ph-2-OCH_Three      H
H H H CH_Three      F Cl H Ph-3-OCH_Three      H
H H H CH_Three      F Cl H Ph-4-OCH_Three      H
H H H CH_Three      F Cl H Ph-4-OCHF₂    H
H H H CH_Three      F Cl H Ph-4-OCF_Three      H
H H H CH_Three      F Cl H Ph-2,4-F₂      H
H H H CH_Three      F Cl H Ph-3,4-F₂      H
H H H CH_Three      F Cl H Ph-3-Cl-4-F H
H H H CH_Three      F Cl H Ph-2-F-4-Cl H
H H H CH_Three      F Cl H Ph-3-F-4-Cl H
H H H CH_Three      F Cl H Ph-3,4-Cl₂      H
H H H CH_Three      F Cl H Ph-2-F-4-CH_Three     H
H H H CH_Three      F Cl H Ph-2-CH_Three-4-Cl H
H H H CH_Three      F Cl H Ph-2-F-4-CF_Three     H
H H H CH_Three      F Cl H Ph-3-F-4-CF_Three     H
H H H CH_Three      F Cl H Ph-2-F-4-OCF_Three    H
H H H CH_Three      F Cl H Ph-3-F-4-OCF_Three    H
H H H CH_Three      F Cl H T-15 H
H H H CH_Three      F Cl H Ph-2,4,5-F_Three     H
H H H CH_Three      F Cl H Ph-2,4,6-F_Three     H
H H H CH_Three      F Cl H Ph-3,4,5-F_Three     H
H H H CH_Three      F Cl H D-1-2a H
H H H CH_Three      F Cl H (D-1-2b) -2-CH_Three    H
H H H CH_Three      F Cl H (D-2-1b) -5-F H
H H H CH_Three      F Cl H (D-8-2b) -2-CH_Three    H
H H H CH_Three      F Cl H (D-23-2b) -6-F H
H H H CH_Three      F Cl H (D-23-2b) -6-Cl H
H H H CH_Three      CH_Three      Cl H Ph-2-F H
H H H CH_Three      CH_Three      Cl H Ph-3-F H
H H H CH_Three      CH_Three      Cl H Ph-4-F H
H H H CH_Three      CH_Three      Cl H Ph-2-Cl H
H H H CH_Three      CH_Three      Cl H Ph-3-Cl H
H H H CH_Three      CH_Three      Cl H Ph-4-Cl H
H H H CH_Three      CH_Three      Cl H Ph-2-CH_Three       H
H H H CH_Three      CH_Three      Cl H Ph-3-CH_Three       H
H H H CH_Three      CH_Three      Cl H Ph-4-CH_Three       H
H H H CH_Three      CH_Three      Cl H Ph-2-CF_Three       H
H H H CH_Three      CH_Three      Cl H Ph-3-CF_Three       H
H H H CH_Three      CH_Three      Cl H Ph-4-CF_Three       H
H H H CH_Three      CH_Three      Cl H Ph-2-OCH_Three      H
H H H CH_Three      CH_Three      Cl H Ph-3-OCH_Three      H
H H H CH_Three      CH_Three      Cl H Ph-4-OCH_Three      H
H H H CH_Three      CH_Three      Cl H Ph-4-OCHF₂     H
H H H CH_Three      CH_Three      Cl H Ph-4-OCF_Three      H
H H H CH_Three      CH_Three      Cl H Ph-2,4-F₂      H
H H H CH_Three      CH_Three      Cl H Ph-3,4-F₂      H
H H H CH_Three      CH_Three      Cl H Ph-3-Cl-4-F H
H H H CH_Three      CH_Three      Cl H Ph-2-F-4-Cl H
H H H CH_Three      CH_Three      Cl H Ph-3-F-4-Cl H
H H H CH_Three      CH_Three      Cl H Ph-3,4-Cl₂      H
H H H CH_Three      CH_Three      Cl H Ph-2-F-4-CH_Three     H
H H H CH_Three      CH_Three      Cl H Ph-2-CH_Three-4-Cl H
H H H CH_Three      CH_Three      Cl H Ph-2-F-4-CF_Three     H
H H H CH_Three      CH_Three      Cl H Ph-3-F-4-CF_Three     H
H H H CH_Three      CH_Three      Cl H Ph-2-F-4-OCF_Three    H
H H H CH_Three      CH_Three      Cl H Ph-3-F-4-OCF_Three    H
H H H CH_Three      CH_Three      Cl H T-15 H
H H H CH_Three      CH_Three      Cl H Ph-2,4,5-F_Three     H
H H H CH_Three      CH_Three      Cl H Ph-2,4,6-F_Three     H
H H H CH_Three      CH_Three      Cl H Ph-3,4,5-F_Three     H
H H H CH_Three      CH_Three      Cl H D-1-2a H
H H H CH_Three      CH_Three      Cl H (D-1-2b) -2-CH_Three    H
H H H CH_Three      CH_Three      Cl H (D-2-1b) -5-F H
H H H CH_Three      CH_Three      Cl H (D-8-2b) -2-CH_Three    H
H H H CH_Three      CH_Three      Cl H (D-23-2b) -6-F H
H H H CH_Three      CH_Three      Cl H (D-23-2b) -6-Cl H
H H H Et H Cl H Ph-2-F H
H H H Et H Cl H Ph-3-F H
H H H Et H Cl H Ph-4-F H
H H H Et CH_Three      Cl H Ph-2-F H
H H H Et CH_Three      Cl H Ph-3-F H
H H H Et CH_Three      Cl H Ph-4-F H
H H H n-Pr H Cl H Ph-2-F H
H H H n-Pr H Cl H Ph-3-F H
H H H n-Pr H Cl H Ph-4-F H
H H H i-Pr H Cl H Ph-2-F H
H H H i-Pr H Cl H Ph-3-F H
H H H i-Pr H Cl H Ph-4-F H
H H H c-Pr H Cl H Ph-2-F H
H H H c-Pr H Cl H Ph-3-F H
H H H c-Pr H Cl H Ph-4-F H
H H H CH₂CF_Three     H Cl H Ph-2-F H
H H H CH₂CF_Three     H Cl H Ph-3-F H
H H H CH₂CF_Three     H Cl H Ph-4-F H
H H H -CH₂-Cl H Ph-2-F H
H H H -CH₂-Cl H Ph-3-F H
H H H -CH₂-Cl H Ph-4-F H
H H H -CH₂-Cl H Ph-2-Cl H
H H H -CH₂-Cl H Ph-3-Cl H
H H H -CH₂-Cl H Ph-4-Cl H
H H H -CH₂-Cl H Ph-2-CH_Three       H
H H H -CH₂-Cl H Ph-3-CH_Three       H
H H H -CH₂-Cl H Ph-4-CH_Three       H
H H H -CH₂-Cl H Ph-2-CF_Three       H
H H H -CH₂-Cl H Ph-3-CF_Three       H
H H H -CH₂-Cl H Ph-4-CF_Three       H
H H H -CH₂-Cl H Ph-2-OCH_Three      H
H H H -CH₂-Cl H Ph-3-OCH_Three      H
H H H -CH₂-Cl H Ph-4-OCH_Three      H
H H H -CH₂-Cl H Ph-4-OCF_Three      H
H H H -CH₂-Cl H Ph-2,4-F₂      H
H H H -CH₂-Cl H Ph-3,4-F₂      H
H H H -CH₂-Cl H Ph-3-Cl-4-F H
H H H -CH₂-Cl H Ph-2-F-4-Cl H
H H H -CH₂-Cl H Ph-3-F-4-Cl H
H H H -CH₂-Cl H Ph-3,4-Cl₂      H
H H H -CH₂-Cl H Ph-2-F-4-CH_Three     H
H H H -CH₂-Cl H Ph-2-CH_Three-4-Cl H
H H H -CH₂-Cl H Ph-2-F-4-CF_Three     H
H H H -CH₂-Cl H Ph-3-F-4-CF_Three     H
H H H -CH₂-Cl H Ph-2-F-4-OCF_Three    H
H H H -CH₂-Cl H Ph-3-F-4-OCF_Three    H
H H H -CH₂-Cl H T-15 H
H H H -CH₂-Cl H Ph-2,4,5-F_Three     H
H H H -CH₂-Cl H Ph-2,4,6-F_Three     H
H H H -CH₂-Cl H Ph-3,4,5-F_Three     H
H H H -CH₂-Cl H D-1-2a H
H H H -CH₂-Cl H (D-1-2b) -2-CH_Three    H
H H H -CH₂-Cl H (D-2-1b) -5-F H
H H H -CH₂-Cl H (D-8-2b) -2-CH_Three    H
H H H -CH₂-Cl H (D-23-2b) -6-F H
H H H -CH₂-Cl H (D-23-2b) -6-Cl H
H H H -CH₂-Br H Ph-2-F H
H H H -CH₂-Br H Ph-3-F H
H H H -CH₂-Br H Ph-4-F H
H H H -CH (F)-Cl H Ph-2-F H
H H H -CH (F)-(E) Cl H Ph-2-F H
H H H -CH (F)-(Z) Cl H Ph-2-F H
H H H -CH (F)-Cl H Ph-3-F H
H H H -CH (F)-(E) Cl H Ph-3-F H
H H H -CH (F)-(Z) Cl H Ph-3-F H
H H H -CH (F)-Cl H Ph-4-F H
H H H -CH (F)-(E) Cl H Ph-4-F H
H H H -CH (F)-(Z) Cl H Ph-4-F H
H H H -CH (Cl)-Cl H Ph-2-F H
H H H -CH (Cl)-(E) Cl H Ph-2-F H
H H H -CH (Cl)-(Z) Cl H Ph-2-F H
H H H -CH (Cl)-Cl H Ph-3-F H
H H H -CH (Cl)-(E) Cl H Ph-3-F H
H H H -CH (Cl)-(Z) Cl H Ph-3-F H
H H H -CH (Cl)-Cl H Ph-4-F H
H H H -CH (Cl)-(E) Cl H Ph-4-F H
H H H -CH (Cl)-(Z) Cl H Ph-4-F H
H H H -CH (CH_Three)-Cl H Ph-2-F H
H H H -CH (CH_Three)-(E) Cl H Ph-2-F H
H H H -CH (CH_Three)-(Z) Cl H Ph-2-F H
H H H -CH (CH_Three)-Cl H Ph-3-F H
H H H -CH (CH_Three)-(E) Cl H Ph-3-F H
H H H -CH (CH_Three)-(Z) Cl H Ph-3-F H
H H H -CH (CH_Three)-Cl H Ph-4-F H
H H H -CH (CH_Three)-(E) Cl H Ph-4-F H
H H H -CH (CH_Three)-(Z) Cl H Ph-4-F H
H H H -CH₂CH₂-Cl H Ph-2-F H
H H H -CH₂CH₂-Cl H Ph-3-F H
H H H -CH₂CH₂-Cl H Ph-4-F H
H H H -CH₂CH₂-Cl H Ph-2-Cl H
H H H -CH₂CH₂-Cl H Ph-3-Cl H
H H H -CH₂CH₂-Cl H Ph-4-Cl H
H H H -CH₂CH₂-Cl H Ph-2-CH_Three       H
H H H -CH₂CH₂-Cl H Ph-3-CH_Three       H
H H H -CH₂CH₂-Cl H Ph-4-CH_Three       H
H H H -CH₂CH₂-Cl H Ph-2-CF_Three       H
H H H -CH₂CH₂-Cl H Ph-3-CF_Three       H
H H H -CH₂CH₂-Cl H Ph-4-CF_Three       H
H H H -CH₂CH₂-Cl H Ph-2-OCH_Three      H
H H H -CH₂CH₂-Cl H Ph-3-OCH_Three      H
H H H -CH₂CH₂-Cl H Ph-4-OCH_Three      H
H H H -CH₂CH₂-Cl H Ph-4-OCHF₂     H
H H H -CH₂CH₂-Cl H Ph-4-OCF_Three      H
H H H -CH₂CH₂-Cl H Ph-2,4-F₂      H
H H H -CH₂CH₂-Cl H Ph-3,4-F₂      H
H H H -CH₂CH₂-Cl H Ph-3-Cl-4-F H
H H H -CH₂CH₂-Cl H Ph-2-F-4-Cl H
H H H -CH₂CH₂-Cl H Ph-3-F-4-Cl H
H H H -CH₂CH₂-Cl H Ph-3,4-Cl₂      H
H H H -CH₂CH₂-Cl H Ph-2-F-4-CH_Three     H
H H H -CH₂CH₂-Cl H Ph-2-CH_Three-4-Cl H
H H H -CH₂CH₂-Cl H Ph-2-F-4-CF_Three     H
H H H -CH₂CH₂-Cl H Ph-3-F-4-CF_Three     H
H H H -CH₂CH₂-Cl H Ph-2-F-4-OCF_Three    H
H H H -CH₂CH₂-Cl H Ph-3-F-4-OCF_Three    H
H H H -CH₂CH₂-Cl H T-15 H
H H H -CH₂CH₂-Cl H Ph-2,4,5-F_Three     H
H H H -CH₂CH₂-Cl H Ph-2,4,6-F_Three     H
H H H -CH₂CH₂-Cl H Ph-3,4,5-F_Three     H
H H H -CH₂CH₂-Cl H D-1-2a H
H H H -CH₂CH₂-Cl H (D-1-2b) -2-CH_Three    H
H H H -CH₂CH₂-Cl H (D-2-1b) -5-F H
H H H -CH₂CH₂-Cl H (D-8-2b) -2-CH_Three    H
H H H -CH₂CH₂-Cl H (D-23-2b) -6-F H
H H H -CH₂CH₂-Cl H (D-23-2b) -6-Cl H
H H H -CH₂CH₂-Br H Ph-2-F H
H H H -CH₂CH₂-Br H Ph-3-F H
H H H -CH₂CH₂-Br H Ph-4-F H
H H H -CH₂CH₂-CH_Three     H Ph-2-F H
H H H -CH₂CH₂-CH_Three     H Ph-3-F H
H H H -CH₂CH₂-CH_Three     H Ph-4-F H
H H H -CH₂CH₂-OCH_Three     H Ph-2-F H
H H H -CH₂CH₂-OCH_Three     H Ph-3-F H
H H H -CH₂CH₂-OCH_Three     H Ph-4-F H
H H H -CH₂CH₂CH₂-Cl H Ph-2-F H
H H H -CH₂CH₂CH₂-Cl H Ph-3-F H
H H H -CH₂CH₂CH₂-Cl H Ph-4-F H
H H H -CH₂OCH₂-Cl H Ph-2-F H
H H H -CH₂OCH₂-Cl H Ph-3-F H
H H H -CH₂OCH₂-Cl H Ph-4-F H
H H H -CH₂SCH₂-Cl H Ph-2-F H
H H H -CH₂SCH₂-Cl H Ph-3-F H
H H H -CH₂SCH₂-Cl H Ph-4-F H
H H H -CH₂S (O) CH₂-Cl H Ph-2-F H
H H H -CH₂S (O) CH₂-Cl H Ph-3-F H
H H H -CH₂S (O) CH₂-Cl H Ph-4-F H
H H H -CH₂SO₂CH₂-Cl H Ph-2-F H
H H H -CH₂SO₂CH₂-Cl H Ph-3-F H
H H H -CH₂SO₂CH₂-Cl H Ph-4-F H
H H H -CH₂CH₂CH₂CH₂-Cl H Ph-2-F H
H H H -CH₂CH₂CH₂CH₂-Cl H Ph-3-F H
H H H -CH₂CH₂CH₂CH₂-Cl H Ph-4-F H
H H H OCH_Three      H Cl H Ph-2-F H
H H H OCH_Three      H Cl H Ph-3-F H
H H H OCH_Three      H Cl H Ph-4-F H
H H H OCH_Three      H Cl H Ph-2-Cl H
H H H OCH_Three      H Cl H Ph-3-Cl H
H H H OCH_Three      H Cl H Ph-4-Cl H
H H H OCH_Three      H Cl H Ph-2-CH_Three       H
H H H OCH_Three      H Cl H Ph-3-CH_Three       H
H H H OCH_Three      H Cl H Ph-4-CH_Three       H
H H H OCH_Three      H Cl H Ph-2-CF_Three       H
H H H OCH_Three      H Cl H Ph-3-CF_Three       H
H H H OCH_Three      H Cl H Ph-4-CF_Three       H
H H H OCH_Three      H Cl H Ph-2-OCH_Three      H
H H H OCH_Three      H Cl H Ph-3-OCH_Three      H
H H H OCH_Three      H Cl H Ph-4-OCH_Three      H
H H H OCH_Three      H Cl H Ph-4-OCHF₂     H
H H H OCH_Three      H Cl H Ph-4-OCF_Three      H
H H H OCH_Three      H Cl H Ph-2,4-F₂      H
H H H OCH_Three      H Cl H Ph-3,4-F₂      H
H H H OCH_Three      H Cl H Ph-3-Cl-4-F H
H H H OCH_Three      H Cl H Ph-2-F-4-Cl H
H H H OCH_Three      H Cl H Ph-3-F-4-Cl H
H H H OCH_Three      H Cl H Ph-3,4-Cl₂      H
H H H OCH_Three      H Cl H Ph-2-F-4-CH_Three     H
H H H OCH_Three      H Cl H Ph-2-CH_Three-4-Cl H
H H H OCH_Three      H Cl H Ph-2-F-4-CF_Three     H
H H H OCH_Three      H Cl H Ph-3-F-4-CF_Three     H
H H H OCH_Three      H Cl H Ph-2-F-4-OCF_Three    H
H H H OCH_Three      H Cl H Ph-3-F-4-OCF_Three    H
H H H OCH_Three      H Cl H T-15 H
H H H OCH_Three      H Cl H Ph-2,4,5-F_Three     H
H H H OCH_Three      H Cl H Ph-2,4,6-F_Three     H
H H H OCH_Three      H Cl H Ph-3,4,5-F_Three     H
H H H OCH_Three      H Cl H D-1-2a H
H H H OCH_Three      H Cl H (D-1-2b) -2-CH_Three    H
H H H OCH_Three      H Cl H (D-2-1b) -5-F H
H H H OCH_Three      H Cl H (D-8-2b) -2-CH_Three    H
H H H OCH_Three      H Cl H (D-23-2b) -6-F H
H H H OCH_Three      H Cl H (D-23-2b) -6-Cl H
H H H OEt H Cl H Ph-2-F H
H H H OEt H Cl H Ph-3-F H
H H H OEt H Cl H Ph-4-F H
H H H OEt H Cl H Ph-2-Cl H
H H H OEt H Cl H Ph-3-Cl H
H H H OEt H Cl H Ph-4-Cl H
H H H OEt H Cl H Ph-2-CH_Three       H
H H H OEt H Cl H Ph-3-CH_Three       H
H H H OEt H Cl H Ph-4-CH_Three       H
H H H OEt H Cl H Ph-2-CF_Three       H
H H H OEt H Cl H Ph-3-CF_Three       H
H H H OEt H Cl H Ph-4-CF_Three       H
H H H OEt H Cl H Ph-2-OCH_Three      H
H H H OEt H Cl H Ph-3-OCH_Three      H
H H H OEt H Cl H Ph-4-OCH_Three      H
H H H OEt H Cl H Ph-4-OCHF₂     H
H H H OEt H Cl H Ph-4-OCF_Three      H
H H H OEt H Cl H Ph-2,4-F₂      H
H H H OEt H Cl H Ph-3,4-F₂      H
H H H OEt H Cl H Ph-3-Cl-4-F H
H H H OEt H Cl H Ph-2-F-4-Cl H
H H H OEt H Cl H Ph-3-F-4-Cl H
H H H OEt H Cl H Ph-3,4-Cl₂      H
H H H OEt H Cl H Ph-2-F-4-CH_Three     H
H H H OEt H Cl H Ph-2-CH_Three-4-Cl H
H H H OEt H Cl H Ph-2-F-4-CF_Three     H
H H H OEt H Cl H Ph-3-F-4-CF_Three     H
H H H OEt H Cl H Ph-2-F-4-OCF_Three    H
H H H OEt H Cl H Ph-3-F-4-OCF_Three    H
H H H OEt H Cl H T-15 H
H H H OEt H Cl H Ph-2,4,5-F_Three     H
H H H OEt H Cl H Ph-2,4,6-F_Three     H
H H H OEt H Cl H Ph-3,4,5-F_Three     H
H H H OEt H Cl H D-1-2a H
H H H OEt H Cl H (D-1-2b) -2-CH_Three    H
H H H OEt H Cl H (D-2-1b) -5-F H
H H H OEt H Cl H (D-8-2b) -2-CH_Three    H
H H H OEt H Cl H (D-23-2b) -6-F H
H H H OEt H Cl H (D-23-2b) -6-Cl H
H H H OPr-n H Cl H Ph-2-F H
H H H OPr-n H Cl H Ph-3-F H
H H H OPr-n H Cl H Ph-4-F H
H H H OPr-i H Cl H Ph-2-F H
H H H OPr-i H Cl H Ph-3-F H
H H H OPr-i H Cl H Ph-4-F H
H H H OCH₂CF_Three    H Cl H Ph-2-F H
H H H OCH₂CF_Three    H Cl H Ph-3-F H
H H H OCH₂CF_Three    H Cl H Ph-4-F H
H H H OCH₂CH = CH₂   H Cl H Ph-2-F H
H H H OCH₂CH = CH₂   H Cl H Ph-3-F H
H H H OCH₂CH = CH₂   H Cl H Ph-4-F H
H H H OCH₂C≡CH H Cl H Ph-2-F H
H H H OCH₂C≡CH H Cl H Ph-3-F H
H H H OCH₂C≡CH H Cl H Ph-4-F H
H H H -OCH₂CH₂-Cl H Ph-2-F H
H H H -OCH₂CH₂-Cl H Ph-3-F H
H H H -OCH₂CH₂-Cl H Ph-4-F H
H H H SCH_Three      H Cl H Ph-2-F H
H H H SCH_Three      H Cl H Ph-3-F H
H H H SCH_Three      H Cl H Ph-4-F H
H H H NHOCH_Three     H Cl H Ph-2-F H
H H H NHOCH_Three     H Cl H Ph-3-F H
H H H NHOCH_Three     H Cl H Ph-4-F H
H H H NHOEt H Cl H Ph-2-F H
H H H NHOEt H Cl H Ph-3-F H
H H H NHOEt H Cl H Ph-4-F H
H H H NHOPr-i H Cl H Ph-2-F H
H H H NHOPr-i H Cl H Ph-3-F H
H H H NHOPr-i H Cl H Ph-4-F H
H H H NHOBu-s H Cl H Ph-2-F H
H H H NHOBu-s H Cl H Ph-3-F H
H H H NHOBu-s H Cl H Ph-4-F H
H H H NHOBu-t H Cl H Ph-2-F H
H H H NHOBu-t H Cl H Ph-3-F H
H H H NHOBu-t H Cl H Ph-4-F H
H H H CN CH_Three      Cl H Ph-2-F H
H H H CN CH_Three      Cl H Ph-3-F H
H H H CN CH_Three      Cl H Ph-4-F H
H H H C (O) NH₂     CH_Three      Cl H Ph-2-F H
H H H C (O) NH₂     CH_Three      Cl H Ph-3-F H
H H H C (O) NH₂     CH_Three      Cl H Ph-4-F H
H H H C (S) NH₂     CH_Three      Cl H Ph-2-F H
H H H C (S) NH₂     CH_Three      Cl H Ph-3-F H
H H H C (S) NH₂     CH_Three      Cl H Ph-4-F H
H CH_Three     H H H Cl H Ph-2-F H
H CH_Three(S) H H H Cl H Ph-2-F H
H CH_Three     H H H Cl H Ph-3-F H
H CH_Three(S) H H H Cl H Ph-3-F H
H CH_Three     H H H Cl H Ph-4-F H
H CH_Three(S) H H H Cl H Ph-4-F H
H CH_Three     H H H Cl H Ph-2-Cl H
H CH_Three(S) H H H Cl H Ph-2-Cl H
H CH_Three     H H H Cl H Ph-3-Cl H
H CH_Three(S) H H H Cl H Ph-3-Cl H
H CH_Three     H H H Cl H Ph-4-Cl H
H CH_Three(S) H H H Cl H Ph-4-Cl H
H CH_Three     H H H Cl H Ph-2-CH_Three       H
H CH_Three(S) H H H Cl H Ph-2-CH_Three       H
H CH_Three     H H H Cl H Ph-3-CH_Three       H
H CH_Three(S) H H H Cl H Ph-3-CH_Three       H
H CH_Three     H H H Cl H Ph-4-CH_Three       H
H CH_Three(S) H H H Cl H Ph-4-CH_Three       H
H CH_Three     H H H Cl H Ph-2-CF_Three       H
H CH_Three(S) H H H Cl H Ph-2-CF_Three       H
H CH_Three     H H H Cl H Ph-3-CF_Three       H
H CH_Three(S) H H H Cl H Ph-3-CF_Three       H
H CH_Three     H H H Cl H Ph-4-CF_Three       H
H CH_Three(S) H H H Cl H Ph-4-CF_Three       H
H CH_Three     H H H Cl H Ph-2-OCH_Three      H
H CH_Three(S) H H H Cl H Ph-2-OCH_Three      H
H CH_Three     H H H Cl H Ph-3-OCH_Three      H
H CH_Three(S) H H H Cl H Ph-3-OCH_Three      H
H CH_Three     H H H Cl H Ph-4-OCH_Three      H
H CH_Three(S) H H H Cl H Ph-4-OCH_Three      H
H CH_Three     H H H Cl H Ph-4-OCHF₂     H
H CH_Three(S) H H H Cl H Ph-4-OCHF₂     H
H CH_Three     H H H Cl H Ph-4-OCF_Three      H
H CH_Three(S) H H H Cl H Ph-4-OCF_Three      H
H CH_Three     H H H Cl H Ph-2,4-F₂      H
H CH_Three(S) H H H Cl H Ph-2,4-F₂      H
H CH_Three     H H H Cl H Ph-3,4-F₂      H
H CH_Three(S) H H H Cl H Ph-3,4-F₂      H
H CH_Three     H H H Cl H Ph-3-Cl-4-F H
H CH_Three(S) H H H Cl H Ph-3-Cl-4-F H
H CH_Three     H H H Cl H Ph-2-F-4-Cl H
H CH_Three(S) H H H Cl H Ph-2-F-4-Cl H
H CH_Three     H H H Cl H Ph-3-F-4-Cl H
H CH_Three(S) H H H Cl H Ph-3-F-4-Cl H
H CH_Three     H H H Cl H Ph-3,4-Cl₂      H
H CH_Three(S) H H H Cl H Ph-3,4-Cl₂      H
H CH_Three     H H H Cl H Ph-2-F-4-CH_Three     H
H CH_Three(S) H H H Cl H Ph-2-F-4-CH_Three     H
H CH_Three     H H H Cl H Ph-2-CH_Three-4-Cl H
H CH_Three(S) H H H Cl H Ph-2-CH_Three-4-Cl H
H CH_Three     H H H Cl H Ph-2-F-4-CF_Three     H
H CH_Three(S) H H H Cl H Ph-2-F-4-CF_Three     H
H CH_Three     H H H Cl H Ph-3-F-4-CF_Three     H
H CH_Three(S) H H H Cl H Ph-3-F-4-CF_Three     H
H CH_Three     H H H Cl H Ph-2-F-4-OCF_Three    H
H CH_Three(S) H H H Cl H Ph-2-F-4-OCF_Three    H
H CH_Three     H H H Cl H Ph-3-F-4-OCF_Three    H
H CH_Three(S) H H H Cl H Ph-3-F-4-OCF_Three    H
H CH_Three     H H H Cl H T-15 H
H CH_Three(S) H H H Cl H T-15 H
H CH_Three     H H H Cl H Ph-2,4,5-F_Three     H
H CH_Three(S) H H H Cl H Ph-2,4,5-F_Three     H
H CH_Three     H H H Cl H Ph-2,4,6-F_Three     H
H CH_Three(S) H H H Cl H Ph-2,4,6-F_Three     H
H CH_Three     H H H Cl H Ph-3,4,5-F_Three     H
H CH_Three(S) H H H Cl H Ph-3,4,5-F_Three    H
H CH_Three     H H H Cl H D-1-2a H
H CH_Three(S) H H H Cl H D-1-2a H
H CH_Three     H H H Cl H (D-1-2b) -2-CH_Three    H
H CH_Three(S) H H H Cl H (D-1-2b) -2-CH_Three    H
H CH_Three     H H H Cl H (D-2-1b) -5-F H
H CH_Three(S) H H H Cl H (D-2-1b) -5-F H
H CH_Three     H H H Cl H (D-8-2b) -2-CH_Three    H
H CH_Three(S) H H H Cl H (D-8-2b) -2-CH_Three    H
H CH_Three     H H H Cl H (D-23-2b) -6-F H
H CH_Three(S) H H H Cl H (D-23-2b) -6-F H
H CH_Three     H H H Cl H (D-23-2b) -6-Cl H
H CH_Three(S) H H H Cl H (D-23-2b) -6-Cl H
H CH_Three     H F H Cl H Ph-2-F H
H CH_Three     H F H Cl H Ph-3-F H
H CH_Three     H F H Cl H Ph-4-F H
H CH_Three     H F H Cl H Ph-2-Cl H
H CH_Three     H F H Cl H Ph-3-Cl H
H CH_Three     H F H Cl H Ph-4-Cl H
H CH_Three     H F H Cl H Ph-2-CH_Three       H
H CH_Three     H F H Cl H Ph-3-CH_Three       H
H CH_Three     H F H Cl H Ph-4-CH_Three       H
H CH_Three     H F H Cl H Ph-2-CF_Three       H
H CH_Three     H F H Cl H Ph-3-CF_Three       H
H CH_Three     H F H Cl H Ph-4-CF_Three       H
H CH_Three     H F H Cl H Ph-2-OCH_Three      H
H CH_Three     H F H Cl H Ph-3-OCH_Three      H
H CH_Three     H F H Cl H Ph-4-OCH_Three      H
H CH_Three     H F H Cl H Ph-4-OCHF₂     H
H CH_Three     H F H Cl H Ph-4-OCF_Three      H
H CH_Three    H F H Cl H Ph-2,4-F₂      H
H CH_Three     H F H Cl H Ph-3,4-F₂      H
H CH_Three     H F H Cl H Ph-3-Cl-4-F H
H CH_Three     H F H Cl H Ph-2-F-4-Cl H
H CH_Three     H F H Cl H Ph-3-F-4-Cl H
H CH_Three     H F H Cl H Ph-3,4-Cl₂      H
H CH_Three     H F H Cl H Ph-2-F-4-CH_Three     H
H CH_Three     H F H Cl H Ph-2-CH_Three-4-Cl H
H CH_Three     H F H Cl H Ph-2-F-4-CF_Three     H
H CH_Three     H F H Cl H Ph-3-F-4-CF_Three     H
H CH_Three     H F H Cl H Ph-2-F-4-OCF_Three    H
H CH_Three     H F H Cl H Ph-3-F-4-OCF_Three    H
H CH_Three     H F H Cl H T-15 H
H CH_Three     H F H Cl H Ph-2,4,5-F_Three     H
H CH_Three     H F H Cl H Ph-2,4,6-F_Three     H
H CH_Three     H F H Cl H Ph-3,4,5-F_Three     H
H CH_Three     H F H Cl H D-1-2a H
H CH_Three     H F H Cl H (D-1-2b) -2-CH_Three    H
H CH_Three     H F H Cl H (D-2-1b) -5-F H
H CH_Three     H F H Cl H (D-8-2b) -2-CH_Three    H
H CH_Three     H F H Cl H (D-23-2b) -6-F H
H CH_Three     H F H Cl H (D-23-2b) -6-Cl H
H CH_Three     H F F Cl H H H
H CH_Three     H F F Cl H Cl H
H CH_Three     H F F Cl H Br H
H CH_Three     H F F Cl H I H
H CH_Three     H F F Cl H CH_Three         H
H CH_Three(S) H F F Cl H CH_Three         H
H CH_Three     H F F Cl H Et H
H CH_Three(S) H F F Cl H Et H
H CH_Three     H F F Cl H n-Pr H
H CH_Three(S) H F F Cl H n-Pr H
H CH_Three     H F F Cl H i-Pr H
H CH_Three(S) H F F Cl H i-Pr H
H CH_Three     H F F Cl H c-Pr H
H CH_Three(S) H F F Cl H c-Pr H
H CH_Three     H F F Cl H T-2 H
H CH_Three(S) H F F Cl H T-2 H
H CH_Three     H F F Cl H c-Bu H
H CH_Three(S) H F F Cl H c-Bu H
H CH_Three     H F F Cl H t-Bu H
H CH_Three(S) H F F Cl H t-Bu H
H CH_Three     H F F Cl H T-1 H
H CH_Three(S) H F F Cl H T-1 H
H CH_Three     H F F Cl H T-3 H
H CH_Three     H F F Cl H c-Pen H
H CH_Three     H F F Cl H T-10 H
H CH_Three     H F F Cl H T-11 H
H CH_Three     H F F Cl H c-Hex H
H CH_Three     H F F Cl H CH₂F H
H CH_Three(S) H F F Cl H CH₂F H
H CH_Three     H F F Cl H CHF₂         H
H CH_Three     H F F Cl H CF_Three         H
H CH_Three     H F F Cl H C (CH_Three)₂F H
H CH_Three(S) H F F Cl H C (CH_Three)₂F H
H CH_Three     H F F Cl H T-4 H
H CH_Three(S) H F F Cl H T-4 H
H CH_Three     H F F Cl H T-5 H
H CH_Three(S) H F F Cl H T-5 H
H CH_Three     H F F Cl H T-6 H
H CH_Three(S) H F F Cl H T-6 H
H CH_Three     H F F Cl H T-7 H
H CH_Three(S) H F F Cl H T-7 H
H CH_Three     H F F Cl H T-8 H
H CH_Three     H F F Cl H T-13 H
H CH_Three(S) H F F Cl H T-13 H
H CH_Three     H F F Cl H T-9 H
H CH_Three     H F F Cl H T-14 H
H CH_Three     H F F Cl H CH₂OCH_Three       H
H CH_Three(S) H F F Cl H CH₂OCH_Three       H
H CH_Three     H F F Cl H CH₂OEt H
H CH_Three     H F F Cl H CH₂OBu-t H
H CH_Three     H F F Cl H CH₂OCH₂CF_Three      H
H CH_Three     H F F Cl H CH₂OCH₂OCH_Three     H
H CH_Three     H F F Cl H C (CH_Three)₂OH H
H CH_Three     H F F Cl H C (CH_Three)₂OCH_Three     H
H CH_Three(S) H F F Cl H C (CH_Three)₂OCH_Three     H
H CH_Three     H F F Cl H C (CH_Three)₂OCH₂CF_Three    H
H CH_Three     H F F Cl H CH (OCH_Three)₂      H
H CH_Three     H F F Cl H T-12 H
H CH_Three     H F F Cl H Si (CH_Three)_Three       H
H CH_Three(S) H F F Cl H Si (CH_Three)_Three       H
H CH_Three     H F F Cl H Si (CH_Three)₂Bu-t H
H CH_Three     H F F Cl H Si (CH_Three)₂Ph H
H CH_Three     H F F Cl H CH = NOCH_Three       H
H CH_Three     H F F Cl H C (CH_Three) = NOCH_Three     H
H CH_Three     H F F Cl H Ph H
H CH_Three     H F F Cl H Ph-2-F H
H CH_Three(S) H F F Cl H Ph-2-F H
H CH_Three     H F F Cl H Ph-3-F H
H CH_Three(S) H F F Cl H Ph-3-F H
H CH_Three     H F F Cl H Ph-4-F H
H CH_Three(S) H F F Cl H Ph-4-F H
H CH_Three     H F F Cl H Ph-2-Cl H
H CH_Three(S) H F F Cl H Ph-2-Cl H
H CH_Three     H F F Cl H Ph-3-Cl H
H CH_Three(S) H F F Cl H Ph-3-Cl H
H CH_Three     H F F Cl H Ph-4-Cl H
H CH_Three(S) H F F Cl H Ph-4-Cl H
H CH_Three     H F F Cl H Ph-2-CH_Three       H
H CH_Three(S) H F F Cl H Ph-2-CH_Three       H
H CH_Three     H F F Cl H Ph-3-CH_Three       H
H CH_Three(S) H F F Cl H Ph-3-CH_Three       H
H CH_Three     H F F Cl H Ph-4-CH_Three       H
H CH_Three(S) H F F Cl H Ph-4-CH_Three       H
H CH_Three     H F F Cl H Ph-2-CF_Three       H
H CH_Three(S) H F F Cl H Ph-2-CF_Three       H
H CH_Three     H F F Cl H Ph-3-CF_Three       H
H CH_Three(S) H F F Cl H Ph-3-CF_Three       H
H CH_Three     H F F Cl H Ph-4-CF_Three       H
H CH_Three(S) H F F Cl H Ph-4-CF_Three       H
H CH_Three     H F F Cl H Ph-2-OCH_Three      H
H CH_Three(S) H F F Cl H Ph-2-OCH_Three      H
H CH_Three     H F F Cl H Ph-3-OCH_Three      H
H CH_Three(S) H F F Cl H Ph-3-OCH_Three      H
H CH_Three     H F F Cl H Ph-4-OCH_Three      H
H CH_Three(S) H F F Cl H Ph-4-OCH_Three      H
H CH_Three     H F F Cl H Ph-4-OCHF₂     H
H CH_Three(S) H F F Cl H Ph-4-OCHF₂     H
H CH_Three     H F F Cl H Ph-4-OCF_Three      H
H CH_Three(S) H F F Cl H Ph-4-OCF_Three      H
H CH_Three     H F F Cl H Ph-4-SCF_Three      H
H CH_Three(S) H F F Cl H Ph-4-SCF_Three      H
H CH_Three     H F F Cl H Ph-4-CN H
H CH_Three(S) H F F Cl H Ph-4-CN H
H CH_Three     H F F Cl H Ph-2,3-F₂      H
H CH_Three(S) H F F Cl H Ph-2,3-F₂      H
H CH_Three     H F F Cl H Ph-2,4-F₂      H
H CH_Three(S) H F F Cl H Ph-2,4-F₂      H
H CH_Three     H F F Cl H Ph-2,5-F₂      H
H CH_Three(S) H F F Cl H Ph-2,5-F₂      H
H CH_Three     H F F Cl H Ph-2,6-F₂      H
H CH_Three(S) H F F Cl H Ph-2,6-F₂      H
H CH_Three     H F F Cl H Ph-3,4-F₂      H
H CH_Three(S) H F F Cl H Ph-3,4-F₂      H
H CH_Three     H F F Cl H Ph-3,5-F₂      H
H CH_Three(S) H F F Cl H Ph-3,5-F₂      H
H CH_Three     H F F Cl H Ph-3-Cl-4-F H
H CH_Three(S) H F F Cl H Ph-3-Cl-4-F H
H CH_Three     H F F Cl H Ph-2-F-4-Cl H
H CH_Three(S) H F F Cl H Ph-2-F-4-Cl H
H CH_Three     H F F Cl H Ph-3-F-4-Cl H
H CH_Three(S) H F F Cl H Ph-3-F-4-Cl H
H CH_Three     H F F Cl H Ph-2,4-Cl₂      H
H CH_Three(S) H F F Cl H Ph-2,4-Cl₂      H
H CH_Three     H F F Cl H Ph-3,4-Cl₂      H
H CH_Three(S) H F F Cl H Ph-3,4-Cl₂      H
H CH_Three     H F F Cl H Ph-2-CH_Three-4-F H
H CH_Three(S) H F F Cl H Ph-2-CH_Three-4-F H
H CH_Three     H F F Cl H Ph-2-F-4-CH_Three     H
H CH_Three(S) H F F Cl H Ph-2-F-4-CH_Three     H
H CH_Three     H F F Cl H Ph-3-F-4-CH_Three     H
H CH_Three(S) H F F Cl H Ph-3-F-4-CH_Three     H
H CH_Three     H F F Cl H Ph-2-CH_Three-4-Cl H
H CH_Three(S) H F F Cl H Ph-2-CH_Three-4-Cl H
H CH_Three     H F F Cl H Ph-3-CH_Three-4-Cl H
H CH_Three(S) H F F Cl H Ph-3-CH_Three-4-Cl H
H CH_Three     H F F Cl H Ph-3-Cl-4-CH_Three    H
H CH_Three(S) H F F Cl H Ph-3-Cl-4-CH_Three    H
H CH_Three     H F F Cl H Ph-2-CF_Three-4-F H
H CH_Three(S) H F F Cl H Ph-2-CF_Three-4-F H
H CH_Three     H F F Cl H Ph-2-F-3-CF_Three     H
H CH_Three(S) H F F Cl H Ph-2-F-3-CF_Three     H
H CH_Three     H F F Cl H Ph-3-CF_Three-4-F H
H CH_Three(S) H F F Cl H Ph-3-CF_Three-4-F H
H CH_Three     H F F Cl H Ph-2-F-4-CF_Three     H
H CH_Three(S) H F F Cl H Ph-2-F-4-CF_Three     H
H CH_Three     H F F Cl H Ph-3-F-4-CF_Three     H
H CH_Three(S) H F F Cl H Ph-3-F-4-CF_Three     H
H CH_Three     H F F Cl H Ph-3-CF_Three-4-Cl H
H CH_Three(S) H F F Cl H Ph-3-CF_Three-4-Cl H
H CH_Three     H F F Cl H Ph-3-Cl-4-CF_Three    H
H CH_Three(S) H F F Cl H Ph-3-Cl-4-CF_Three    H
H CH_Three     H F F Cl H Ph-3-OCH_Three-4-F H
H CH_Three(S) H F F Cl H Ph-3-OCH_Three-4-F H
H CH_Three     H F F Cl H Ph-2-F-4-OCH_Three    H
H CH_Three(S) H F F Cl H Ph-2-F-4-OCH_Three    H
H CH_Three     H F F Cl H Ph-3-F-4-OCH_Three    H
H CH_Three(S) H F F Cl H Ph-3-F-4-OCH_Three    H
H CH_Three     H F F Cl H Ph-3-OCH_Three-4-Cl H
H CH_Three(S) H F F Cl H Ph-3-OCH_Three-4-Cl H
H CH_Three     H F F Cl H Ph-3-Cl-4-OCH_Three    H
H CH_Three(S) H F F Cl H Ph-3-Cl-4-OCH_Three    H
H CH_Three     H F F Cl H Ph-2-F-4-OCHF₂    H
H CH_Three(S) H F F Cl H Ph-2-F-4-OCHF₂    H
H CH_Three     H F F Cl H Ph-3-F-4-OCHF₂    H
H CH_Three(S) H F F Cl H Ph-3-F-4-OCHF₂    H
H CH_Three     H F F Cl H Ph-3-Cl-4-OCHF₂   H
H CH_Three(S) H F F Cl H Ph-3-Cl-4-OCHF₂   H
H CH_Three     H F F Cl H Ph-2-F-4-OCF_Three    H
H CH_Three(S) H F F Cl H Ph-2-F-4-OCF_Three    H
H CH_Three     H F F Cl H Ph-3-F-4-OCF_Three    H
H CH_Three(S) H F F Cl H Ph-3-F-4-OCF_Three    H
H CH_Three     H F F Cl H Ph-2-Cl-4-OCF_Three    H
H CH_Three(S) H F F Cl H Ph-2-Cl-4-OCF_Three    H
H CH_Three     H F F Cl H T-15 H
H CH_Three(S) H F F Cl H T-15 H
H CH_Three     H F F Cl H T-20 H
H CH_Three(S) H F F Cl H T-20 H
H CH_Three     H F F Cl H Ph-2,3,4-F_Three     H
H CH_Three(S) H F F Cl H Ph-2,3,4-F_Three     H
H CH_Three     H F F Cl H Ph-2,4,5-F_Three     H
H CH_Three(S) H F F Cl H Ph-2,4,5-F_Three     H
H CH_Three     H F F Cl H Ph-2,4,6-F_Three     H
H CH_Three(S) H F F Cl H Ph-2,4,6-F_Three     H
H CH_Three     H F F Cl H Ph-3,4,5-F_Three     H
H CH_Three(S) H F F Cl H Ph-3,4,5-F_Three     H
H CH_Three     H F F Cl H Ph-2,5-F₂-4-Cl H
H CH_Three(S) H F F Cl H Ph-2,5-F₂-4-Cl H
H CH_Three     H F F Cl H Ph-2,6-F₂-4-Cl H
H CH_Three(S) H F F Cl H Ph-2,6-F₂-4-Cl H
H CH_Three     H F F Cl H Ph-3,5-F₂-4-Cl H
H CH_Three(S) H F F Cl H Ph-3,5-F₂-4-Cl H
H CH_Three     H F F Cl H Ph-2-F-4-Cl-5-CH_Three  H
H CH_Three(S) H F F Cl H Ph-2-F-4-Cl-5-CH_Three  H
H CH_Three     H F F Cl H Ph-2,5-F₂-4-CF_Three   H
H CH_Three(S) H F F Cl H Ph-2,5-F₂-4-CF_Three   H
H CH_Three     H F F Cl H Ph-2,5-F₂-4-OCH_Three   H
H CH_Three(S) H F F Cl H Ph-2,5-F₂-4-OCH_Three   H
H CH_Three     H F F Cl H Ph-2,6-F₂-4-OCH_Three   H
H CH_Three(S) H F F Cl H Ph-2,6-F₂-4-OCH_Three   H
H CH_Three     H F F Cl H Ph-3,5-F₂-4-OCH_Three   H
H CH_Three(S) H F F Cl H Ph-3,5-F₂-4-OCH_Three   H
H CH_Three     H F F Cl H T-16 H
H CH_Three(S) H F F Cl H T-16 H
H CH_Three     H F F Cl H T-17 H
H CH_Three(S) H F F Cl H T-17 H
H CH_Three     H F F Cl H T-18 H
H CH_Three(S) H F F Cl H T-18 H
H CH_Three     H F F Cl H D-1-2a H
H CH_Three(S) H F F Cl H D-1-2a H
H CH_Three     H F F Cl H (D-1-2b) -2-F H
H CH_Three(S) H F F Cl H (D-1-2b) -2-F H
H CH_Three     H F F Cl H (D-1-2b) -2-CH_Three    H
H CH_Three(S) H F F Cl H (D-1-2b) -2-CH_Three    H
H CH_Three     H F F Cl H (D-1-2b) -4-CH_Three    H
H CH_Three(S) H F F Cl H (D-1-2b) -4-CH_Three    H
H CH_Three     H F F Cl H (D-1-2b) -5-CH_Three    H
H CH_Three(S) H F F Cl H (D-1-2b) -5-CH_Three    H
H CH_Three     H F F Cl H D-2-1a H
H CH_Three(S) H F F Cl H D-2-1a H
H CH_Three     H F F Cl H (D-2-1b) -4-F H
H CH_Three(S) H F F Cl H (D-2-1b) -4-F H
H CH_Three     H F F Cl H (D-2-1b) -5-F H
H CH_Three(S) H F F Cl H (D-2-1b) -5-F H
H CH_Three     H F F Cl H (D-2-1b) -4-Cl H
H CH_Three(S) H F F Cl H (D-2-1b) -4-Cl H
H CH_Three     H F F Cl H (D-2-1b) -5-Cl H
H CH_Three(S) H F F Cl H (D-2-1b) -5-Cl H
H CH_Three     H F F Cl H D-2-2a H
H CH_Three(S) H F F Cl H D-2-2a H
H CH_Three     H F F Cl H (D-2-2b) -5-F H
H CH_Three(S) H F F Cl H (D-2-2b) -5-F H
H CH_Three     H F F Cl H (D-2-2b) -5-Cl H
H CH_Three(S) H F F Cl H (D-2-2b) -5-Cl H
H CH_Three     H F F Cl H (D-2-2b) -5-CH_Three    H
H CH_Three(S) H F F Cl H (D-2-2b) -5-CH_Three    H
H CH_Three     H F F Cl H (D-2-2b) -2-CH_Three-5-Cl H
H CH_Three(S) H F F Cl H (D-2-2b) -2-CH_Three-5-Cl H
H CH_Three     H F F Cl H (D-6-1a) -1-CH_Three    H
H CH_Three(S) H F F Cl H (D-6-1a) -1-CH_Three    H
H CH_Three     H F F Cl H (D-8-2b) -2-CH_Three    H
H CH_Three(S) H F F Cl H (D-8-2b) -2-CH_Three    H
H CH_Three     H F F Cl H (D-23-1b) -5-F H
H CH_Three(S) H F F Cl H (D-23-1b) -5-F H
H CH_Three     H F F Cl H (D-23-1b) -5-Cl H
H CH_Three(S) H F F Cl H (D-23-1b) -5-Cl H
H CH_Three     H F F Cl H (D-23-1b) -5-CF_Three   H
H CH_Three(S) H F F Cl H (D-23-1b) -5-CF_Three   H
H CH_Three     H F F Cl H (D-23-2b) -6-F H
H CH_Three(S) H F F Cl H (D-23-2b) -6-F H
H CH_Three     H F F Cl H (D-23-2b) -6-Cl H
H CH_Three(S) H F F Cl H (D-23-2b) -6-Cl H
H CH_Three     H F F Cl H (D-23-2b) -6-CF_Three   H
H CH_Three(S) H F F Cl H (D-23-2b) -6-CF_Three   H
H CH_Three     H CH_Three      H Cl H Ph-2-F H
H CH_Three     H CH_Three      H Cl H Ph-3-F H
H CH_Three     H CH_Three      H Cl H Ph-4-F H
H CH_Three     H CH_Three      H Cl H Ph-2-Cl H
H CH_Three     H CH_Three      H Cl H Ph-3-Cl H
H CH_Three     H CH_Three      H Cl H Ph-4-Cl H
H CH_Three     H CH_Three      H Cl H Ph-2-CH_Three       H
H CH_Three     H CH_Three      H Cl H Ph-3-CH_Three       H
H CH_Three     H CH_Three      H Cl H Ph-4-CH_Three       H
H CH_Three     H CH_Three      H Cl H Ph-2-CF_Three       H
H CH_Three     H CH_Three      H Cl H Ph-3-CF_Three       H
H CH_Three     H CH_Three      H Cl H Ph-4-CF_Three       H
H CH_Three     H CH_Three      H Cl H Ph-2-OCH_Three      H
H CH_Three     H CH_Three      H Cl H Ph-3-OCH_Three      H
H CH_Three     H CH_Three      H Cl H Ph-4-OCH_Three      H
H CH_Three     H CH_Three      H Cl H Ph-4-OCHF₂     H
H CH_Three     H CH_Three      H Cl H Ph-4-OCF_Three      H
H CH_Three     H CH_Three      H Cl H Ph-2,4-F₂      H
H CH_Three     H CH_Three      H Cl H Ph-3,4-F₂      H
H CH_Three     H CH_Three      H Cl H Ph-3-Cl-4-F H
H CH_Three     H CH_Three      H Cl H Ph-2-F-4-Cl H
H CH_Three     H CH_Three      H Cl H Ph-3-F-4-Cl H
H CH_Three     H CH_Three      H Cl H Ph-3,4-Cl₂      H
H CH_Three     H CH_Three      H Cl H Ph-2-F-4-CH_Three     H
H CH_Three     H CH_Three     H Cl H Ph-2-CH_Three-4-Cl H
H CH_Three     H CH_Three      H Cl H Ph-2-F-4-CF_Three     H
H CH_Three     H CH_Three      H Cl H Ph-3-F-4-CF_Three     H
H CH_Three     H CH_Three      H Cl H Ph-2-F-4-OCF_Three    H
H CH_Three     H CH_Three      H Cl H Ph-3-F-4-OCF_Three    H
H CH_Three     H CH_Three      H Cl H T-15 H
H CH_Three     H CH_Three      H Cl H Ph-2,4,5-F_Three     H
H CH_Three     H CH_Three      H Cl H Ph-2,4,6-F_Three     H
H CH_Three     H CH_Three      H Cl H Ph-3,4,5-F_Three     H
H CH_Three     H CH_Three      H Cl H D-1-2a H
H CH_Three     H CH_Three      H Cl H (D-1-2b) -2-CH_Three    H
H CH_Three     H CH_Three      H Cl H (D-2-1b) -5-F H
H CH_Three     H CH_Three      H Cl H (D-8-2b) -2-CH_Three    H
H CH_Three     H CH_Three      H Cl H (D-23-2b) -6-F H
H CH_Three     H CH_Three      H Cl H (D-23-2b) -6-Cl H
H CH_Three     H CH_Three      F Cl H CH_Three         H
H CH_Three(S) H CH_Three      F Cl H CH_Three         H
H CH_Three     H CH_Three      F Cl H Et H
H CH_Three(S) H CH_Three      F Cl H Et H
H CH_Three     H CH_Three      F Cl H n-Pr H
H CH_Three(S) H CH_Three      F Cl H n-Pr H
H CH_Three     H CH_Three      F Cl H i-Pr H
H CH_Three(S) H CH_Three      F Cl H i-Pr H
H CH_Three     H CH_Three      F Cl H c-Pr H
H CH_Three(S) H CH_Three      F Cl H c-Pr H
H CH_Three     H CH_Three      F Cl H T-2 H
H CH_Three(S) H CH_Three      F Cl H T-2 H
H CH_Three     H CH_Three      F Cl H c-Bu H
H CH_Three(S) H CH_Three      F Cl H c-Bu H
H CH_Three     H CH_Three      F Cl H t-Bu H
H CH_Three(S) H CH_Three      F Cl H t-Bu H
H CH_Three     H CH_Three      F Cl H T-1 H
H CH_Three(S) H CH_Three      F Cl H T-1 H
H CH_Three     H CH_Three      F Cl H CH₂F H
H CH_Three(S) H CH_Three      F Cl H CH₂F H
H CH_Three     H CH_Three      F Cl H C (CH_Three)₂F H
H CH_Three(S) H CH_Three      F Cl H C (CH_Three)₂F H
H CH_Three     H CH_Three      F Cl H T-4 H
H CH_Three(S) H CH_Three      F Cl H T-4 H
H CH_Three     H CH_Three      F Cl H T-5 H
H CH_Three(S) H CH_Three      F Cl H T-5 H
H CH_Three     H CH_Three      F Cl H T-6 H
H CH_Three(S) H CH_Three      F Cl H T-6 H
H CH_Three     H CH_Three      F Cl H T-7 H
H CH_Three(S) H CH_Three      F Cl H T-7 H
H CH_Three     H CH_Three      F Cl H T-8 H
H CH_Three     H CH_Three      F Cl H T-13 H
H CH_Three(S) H CH_Three      F Cl H T-13 H
H CH_Three     H CH_Three      F Cl H T-9 H
H CH_Three     H CH_Three      F Cl H T-14 H
H CH_Three     H CH_Three      F Cl H CH₂OCH_Three       H
H CH_Three(S) H CH_Three      F Cl H CH₂OCH_Three       H
H CH_Three     H CH_Three      F Cl H C (CH_Three)₂OCH_Three     H
H CH_Three(S) H CH_Three      F Cl H C (CH_Three)₂OCH_Three     H
H CH_Three     H CH_Three      F Cl H Si (CH_Three)_Three       H
H CH_Three(S) H CH_Three      F Cl H Si (CH_Three)_Three       H
H CH_Three     H CH_Three      F Cl H Ph-2-F H
H CH_Three     H CH_Three      F Cl H Ph-3-F H
H CH_Three     H CH_Three      F Cl H Ph-4-F H
H CH_Three     H CH_Three      F Cl H Ph-2-Cl H
H CH_Three     H CH_Three      F Cl H Ph-3-Cl H
H CH_Three     H CH_Three      F Cl H Ph-4-Cl H
H CH_Three     H CH_Three      F Cl H Ph-2-CH_Three       H
H CH_Three     H CH_Three      F Cl H Ph-3-CH_Three       H
H CH_Three     H CH_Three      F Cl H Ph-4-CH_Three       H
H CH_Three     H CH_Three      F Cl H Ph-2-CF_Three       H
H CH_Three     H CH_Three      F Cl H Ph-3-CF_Three       H
H CH_Three     H CH_Three      F Cl H Ph-4-CF_Three       H
H CH_Three     H CH_Three      F Cl H Ph-2-OCH_Three      H
H CH_Three     H CH_Three      F Cl H Ph-3-OCH_Three      H
H CH_Three     H CH_Three      F Cl H Ph-4-OCH_Three      H
H CH_Three     H CH_Three      F Cl H Ph-4-OCHF₂     H
H CH_Three     H CH_Three      F Cl H Ph-4-OCF_Three      H
H CH_Three     H CH_Three      F Cl H Ph-2,4-F₂      H
H CH_Three     H CH_Three      F Cl H Ph-3,4-F₂      H
H CH_Three     H CH_Three      F Cl H Ph-3-Cl-4-F H
H CH_Three     H CH_Three      F Cl H Ph-2-F-4-Cl H
H CH_Three     H CH_Three      F Cl H Ph-3-F-4-Cl H
H CH_Three     H CH_Three      F Cl H Ph-3,4-Cl₂      H
H CH_Three     H CH_Three      F Cl H Ph-2-F-4-CH_Three     H
H CH_Three     H CH_Three      F Cl H Ph-2-CH_Three-4-Cl H
H CH_Three     H CH_Three      F Cl H Ph-2-F-4-CF_Three     H
H CH_Three     H CH_Three      F Cl H Ph-3-F-4-CF_Three     H
H CH_Three     H CH_Three      F Cl H Ph-2-F-4-OCF_Three    H
H CH_Three     H CH_Three      F Cl H Ph-3-F-4-OCF_Three    H
H CH_Three     H CH_Three      F Cl H T-15 H
H CH_Three     H CH_Three      F Cl H Ph-2,4,5-F_Three     H
H CH_Three     H CH_Three      F Cl H Ph-2,4,6-F_Three     H
H CH_Three     H CH_Three      F Cl H Ph-3,4,5-F_Three     H
H CH_Three     H CH_Three      F Cl H D-1-2a H
H CH_Three     H CH_Three      F Cl H (D-1-2b) -2-CH_Three    H
H CH_Three     H CH_Three      F Cl H (D-2-1b) -5-F H
H CH_Three     H CH_Three      F Cl H (D-8-2b) -2-CH_Three    H
H CH_Three     H CH_Three      F Cl H (D-23-2b) -6-F H
H CH_Three     H CH_Three      F Cl H (D-23-2b) -6-Cl H
H CH_Three     H -CH₂-Cl H Ph-2-F H
H CH_Three(S) H -CH₂-Cl H Ph-2-F H
H CH_Three     H -CH₂-Cl H Ph-3-F H
H CH_Three(S) H -CH₂-Cl H Ph-3-F H
H CH_Three     H -CH₂-Cl H Ph-4-F H
H CH_Three(S) H -CH₂-Cl H Ph-4-F H
H CH_Three     H -CH₂CH₂-Cl H Ph-2-F H
H CH_Three(S) H -CH₂CH₂-Cl H Ph-2-F H
H CH_Three     H -CH₂CH₂-Cl H Ph-3-F H
H CH_Three(S) H -CH₂CH₂-Cl H Ph-3-F H
H CH_Three     H -CH₂CH₂-Cl H Ph-4-F H
H CH_Three(S) H -CH₂CH₂-Cl H Ph-4-F H
H CH_Three     H OCH_Three      H Cl H Ph-2-F H
H CH_Three(S) H OCH_Three(R) H Cl H Ph-2-F H
H CH_Three(S) H OCH_Three(S) H Cl H Ph-2-F H
H CH_Three     H OCH_Three      H Cl H Ph-3-F H
H CH_Three(S) H OCH_Three(R) H Cl H Ph-3-F H
H CH_Three(S) H OCH_Three(S) H Cl H Ph-3-F H
H CH_Three     H OCH_Three      H Cl H Ph-4-F H
H CH_Three(S) H OCH_Three(R) H Cl H Ph-4-F H
H CH_Three(S) H OCH_Three(S) H Cl H Ph-4-F H
H CH_Three     H OCH_Three      H Cl H Ph-2-Cl H
H CH_Three(S) H OCH_Three(R) H Cl H Ph-2-Cl H
H CH_Three(S) H OCH_Three(S) H Cl H Ph-2-Cl H
H CH_Three     H OCH_Three      H Cl H Ph-3-Cl H
H CH_Three(S) H OCH_Three(R) H Cl H Ph-3-Cl H
H CH_Three(S) H OCH_Three(S) H Cl H Ph-3-Cl H
H CH_Three     H OCH_Three      H Cl H Ph-4-Cl H
H CH_Three(S) H OCH_Three(R) H Cl H Ph-4-Cl H
H CH_Three(S) H OCH_Three(S) H Cl H Ph-4-Cl H
H CH_Three     H OCH_Three      H Cl H Ph-2-CH_Three       H
H CH_Three(S) H OCH_Three(R) H Cl H Ph-2-CH_Three       H
H CH_Three(S) H OCH_Three(S) H Cl H Ph-2-CH_Three       H
H CH_Three     H OCH_Three      H Cl H Ph-3-CH_Three       H
H CH_Three(S) H OCH_Three(R) H Cl H Ph-3-CH_Three       H
H CH_Three(S) H OCH_Three(S) H Cl H Ph-3-CH_Three       H
H CH_Three     H OCH_Three      H Cl H Ph-4-CH_Three       H
H CH_Three(S) H OCH_Three(R) H Cl H Ph-4-CH_Three       H
H CH_Three(S) H OCH_Three(S) H Cl H Ph-4-CH_Three       H
H CH_Three     H OCH_Three      H Cl H Ph-2-CF_Three       H
H CH_Three(S) H OCH_Three(R) H Cl H Ph-2-CF_Three       H
H CH_Three(S) H OCH_Three(S) H Cl H Ph-2-CF_Three       H
H CH_Three     H OCH_Three      H Cl H Ph-3-CF_Three       H
H CH_Three(S) H OCH_Three(R) H Cl H Ph-3-CF_Three       H
H CH_Three(S) H OCH_Three(S) H Cl H Ph-3-CF_Three       H
H CH_Three     H OCH_Three      H Cl H Ph-4-CF_Three       H
H CH_Three(S) H OCH_Three(R) H Cl H Ph-4-CF_Three       H
H CH_Three(S) H OCH_Three(S) H Cl H Ph-4-CF_Three       H
H CH_Three     H OCH_Three      H Cl H Ph-2-OCH_Three      H
H CH_Three(S) H OCH_Three(R) H Cl H Ph-2-OCH_Three      H
H CH_Three(S) H OCH_Three(S) H Cl H Ph-2-OCH_Three      H
H CH_Three     H OCH_Three      H Cl H Ph-3-OCH_Three      H
H CH_Three(S) H OCH_Three(R) H Cl H Ph-3-OCH_Three      H
H CH_Three(S) H OCH_Three(S) H Cl H Ph-3-OCH_Three      H
H CH_Three     H OCH_Three      H Cl H Ph-4-OCH_Three      H
H CH_Three(S) H OCH_Three(R) H Cl H Ph-4-OCH_Three      H
H CH_Three(S) H OCH_Three(S) H Cl H Ph-4-OCH_Three      H
H CH_Three     H OCH_Three      H Cl H Ph-4-OCHF₂     H
H CH_Three(S) H OCH_Three(R) H Cl H Ph-4-OCHF₂     H
H CH_Three(S) H OCH_Three(S) H Cl H Ph-4-OCHF₂     H
H CH_Three     H OCH_Three      H Cl H Ph-4-OCF_Three      H
H CH_Three(S) H OCH_Three(R) H Cl H Ph-4-OCF_Three      H
H CH_Three(S) H OCH_Three(S) H Cl H Ph-4-OCF_Three      H
H CH_Three     H OCH_Three      H Cl H Ph-2,4-F₂      H
H CH_Three(S) H OCH_Three(R) H Cl H Ph-2,4-F₂      H
H CH_Three(S) H OCH_Three(S) H Cl H Ph-2,4-F₂      H
H CH_Three     H OCH_Three      H Cl H Ph-3,4-F₂      H
H CH_Three(S) H OCH_Three(R) H Cl H Ph-3,4-F₂      H
H CH_Three(S) H OCH_Three(S) H Cl H Ph-3,4-F₂      H
H CH_Three     H OCH_Three      H Cl H Ph-3-Cl-4-F H
H CH_Three(S) H OCH_Three(R) H Cl H Ph-3-Cl-4-F H
H CH_Three(S) H OCH_Three(S) H Cl H Ph-3-Cl-4-F H
H CH_Three     H OCH_Three      H Cl H Ph-2-F-4-Cl H
H CH_Three(S) H OCH_Three(R) H Cl H Ph-2-F-4-Cl H
H CH_Three(S) H OCH_Three(S) H Cl H Ph-2-F-4-Cl H
H CH_Three     H OCH_Three      H Cl H Ph-3-F-4-Cl H
H CH_Three(S) H OCH_Three(R) H Cl H Ph-3-F-4-Cl H
H CH_Three(S) H OCH_Three(S) H Cl H Ph-3-F-4-Cl H
H CH_Three     H OCH_Three      H Cl H Ph-3,4-Cl₂      H
H CH_Three(S) H OCH_Three(R) H Cl H Ph-3,4-Cl₂      H
H CH_Three(S) H OCH_Three(S) H Cl H Ph-3,4-Cl₂      H
H CH_Three     H OCH_Three      H Cl H Ph-2-F-4-CH_Three     H
H CH_Three(S) H OCH_Three(R) H Cl H Ph-2-F-4-CH_Three     H
H CH_Three(S) H OCH_Three(S) H Cl H Ph-2-F-4-CH_Three     H
H CH_Three     H OCH_Three      H Cl H Ph-2-CH_Three-4-Cl H
H CH_Three(S) H OCH_Three(R) H Cl H Ph-2-CH_Three-4-Cl H
H CH_Three(S) H OCH_Three(S) H Cl H Ph-2-CH_Three-4-Cl H
H CH_Three     H OCH_Three      H Cl H Ph-2-F-4-CF_Three     H
H CH_Three(S) H OCH_Three(R) H Cl H Ph-2-F-4-CF_Three     H
H CH_Three(S) H OCH_Three(S) H Cl H Ph-2-F-4-CF_Three     H
H CH_Three     H OCH_Three      H Cl H Ph-3-F-4-CF_Three     H
H CH_Three(S) H OCH_Three(R) H Cl H Ph-3-F-4-CF_Three     H
H CH_Three(S) H OCH_Three(S) H Cl H Ph-3-F-4-CF_Three     H
H CH_Three     H OCH_Three      H Cl H Ph-2-F-4-OCF_Three    H
H CH_Three(S) H OCH_Three(R) H Cl H Ph-2-F-4-OCF_Three    H
H CH_Three(S) H OCH_Three(S) H Cl H Ph-2-F-4-OCF_Three    H
H CH_Three     H OCH_Three      H Cl H Ph-3-F-4-OCF_Three    H
H CH_Three(S) H OCH_Three(R) H Cl H Ph-3-F-4-OCF_Three    H
H CH_Three(S) H OCH_Three(S) H Cl H Ph-3-F-4-OCF_Three    H
H CH_Three     H OCH_Three      H Cl H T-15 H
H CH_Three(S) H OCH_Three(R) H Cl H T-15 H
H CH_Three(S) H OCH_Three(S) H Cl H T-15 H
H CH_Three     H OCH_Three      H Cl H Ph-2,4,5-F_Three     H
H CH_Three(S) H OCH_Three(R) H Cl H Ph-2,4,5-F_Three     H
H CH_Three(S) H OCH_Three(S) H Cl H Ph-2,4,5-F_Three     H
H CH_Three     H OCH_Three      H Cl H Ph-2,4,6-F_Three     H
H CH_Three(S) H OCH_Three(R) H Cl H Ph-2,4,6-F_Three     H
H CH_Three(S) H OCH_Three(S) H Cl H Ph-2,4,6-F_Three     H
H CH_Three     H OCH_Three      H Cl H Ph-3,4,5-F_Three     H
H CH_Three(S) H OCH_Three(R) H Cl H Ph-3,4,5-F_Three     H
H CH_Three(S) H OCH_Three(S) H Cl H Ph-3,4,5-F_Three     H
H CH_Three     H OCH_Three      H Cl H D-1-2a H
H CH_Three(S) H OCH_Three(R) H Cl H D-1-2a H
H CH_Three(S) H OCH_Three(S) H Cl H D-1-2a H
H CH_Three     H OCH_Three      H Cl H (D-1-2b) -2-CH_Three    H
H CH_Three(S) H OCH_Three(R) H Cl H (D-1-2b) -2-CH_Three    H
H CH_Three(S) H OCH_Three(S) H Cl H (D-1-2b) -2-CH_Three    H
H CH_Three     H OCH_Three      H Cl H (D-2-1b) -5-F H
H CH_Three(S) H OCH_Three(R) H Cl H (D-2-1b) -5-F H
H CH_Three(S) H OCH_Three(S) H Cl H (D-2-1b) -5-F H
H CH_Three     H OCH_Three      H Cl H (D-8-2b) -2-CH_Three    H
H CH_Three(S) H OCH_Three(R) H Cl H (D-8-2b) -2-CH_Three    H
H CH_Three(S) H OCH_Three(S) H Cl H (D-8-2b) -2-CH_Three    H
H CH_Three     H OCH_Three      H Cl H (D-23-2b) -6-F H
H CH_Three(S) H OCH_Three(R) H Cl H (D-23-2b) -6-F H
H CH_Three(S) H OCH_Three(S) H Cl H (D-23-2b) -6-F H
H CH_Three     H OCH_Three      H Cl H (D-23-2b) -6-Cl H
H CH_Three(S) H OCH_Three(R) H Cl H (D-23-2b) -6-Cl H
H CH_Three(S) H OCH_Three(S) H Cl H (D-23-2b) -6-Cl H
H CH_Three     H OEt H Cl H Ph-2-F H
H CH_Three     H OEt H Cl H Ph-3-F H
H CH_Three     H OEt H Cl H Ph-4-F H
H CH_Three     H OEt H Cl H Ph-2-Cl H
H CH_Three     H OEt H Cl H Ph-3-Cl H
H CH_Three     H OEt H Cl H Ph-4-Cl H
H CH_Three     H OEt H Cl H Ph-2-CH_Three       H
H CH_Three     H OEt H Cl H Ph-3-CH_Three       H
H CH_Three     H OEt H Cl H Ph-4-CH_Three       H
H CH_Three     H OEt H Cl H Ph-2-CF_Three       H
H CH_Three     H OEt H Cl H Ph-3-CF_Three       H
H CH_Three     H OEt H Cl H Ph-4-CF_Three       H
H CH_Three     H OEt H Cl H Ph-2-OCH_Three      H
H CH_Three     H OEt H Cl H Ph-3-OCH_Three      H
H CH_Three     H OEt H Cl H Ph-4-OCH_Three      H
H CH_Three     H OEt H Cl H Ph-4-OCHF₂     H
H CH_Three     H OEt H Cl H Ph-4-OCF_Three      H
H CH_Three     H OEt H Cl H Ph-2,4-F₂      H
H CH_Three     H OEt H Cl H Ph-3,4-F₂      H
H CH_Three     H OEt H Cl H Ph-3-Cl-4-F H
H CH_Three     H OEt H Cl H Ph-2-F-4-Cl H
H CH_Three     H OEt H Cl H Ph-3-F-4-Cl H
H CH_Three     H OEt H Cl H Ph-3,4-Cl₂      H
H CH_Three     H OEt H Cl H Ph-2-F-4-CH_Three     H
H CH_Three     H OEt H Cl H Ph-2-CH_Three-4-Cl H
H CH_Three     H OEt H Cl H Ph-2-F-4-CF_Three     H
H CH_Three     H OEt H Cl H Ph-3-F-4-CF_Three     H
H CH_Three     H OEt H Cl H Ph-2-F-4-OCF_Three    H
H CH_Three     H OEt H Cl H Ph-3-F-4-OCF_Three    H
H CH_Three     H OEt H Cl H T-15 H
H CH_Three     H OEt H Cl H Ph-2,4,5-F_Three     H
H CH_Three     H OEt H Cl H Ph-2,4,6-F_Three     H
H CH_Three     H OEt H Cl H Ph-3,4,5-F_Three     H
H CH_Three     H OEt H Cl H D-1-2a H
H CH_Three     H OEt H Cl H (D-1-2b) -2-CH_Three    H
H CH_Three     H OEt H Cl H (D-2-1b) -5-F H
H CH_Three     H OEt H Cl H (D-8-2b) -2-CH_Three    H
H CH_Three     H OEt H Cl H (D-23-2b) -6-F H
H CH_Three     H OEt H Cl H (D-23-2b) -6-Cl H
H CH_Three     H OPr-n H Cl H Ph-2-F H
H CH_Three     H OPr-n H Cl H Ph-3-F H
H CH_Three     H OPr-n H Cl H Ph-4-F H
H CH_Three     H OPr-i H Cl H Ph-2-F H
H CH_Three     H OPr-i H Cl H Ph-3-F H
H CH_Three     H OPr-i H Cl H Ph-4-F H
H CH_Three     H OCH₂CF_Three    H Cl H Ph-2-F H
H CH_Three     H OCH₂CF_Three    H Cl H Ph-3-F H
H CH_Three     H OCH₂CF_Three    H Cl H Ph-4-F H
H CH_Three     H OCH₂CH = CH₂   H Cl H Ph-2-F H
H CH_Three     H OCH₂CH = CH₂   H Cl H Ph-3-F H
H CH_Three     H OCH₂CH = CH₂   H Cl H Ph-4-F H
H CH_Three     H OCH₂C≡CH H Cl H Ph-2-F H
H CH_Three     H OCH₂C≡CH H Cl H Ph-3-F H
H CH_Three     H OCH₂C≡CH H Cl H Ph-4-F H
H CH_Three     H OCH₂Ph H Cl H Ph-2-F H
H CH_Three     H OCH₂Ph H Cl H Ph-3-F H
H CH_Three     H OCH₂Ph H Cl H Ph-4-F H
H CH_Three     H SCH₂CF_Three    H Cl H Ph-2-F H
H CH_Three     H SCH₂CF_Three    H Cl H Ph-3-F H
H CH_Three     H SCH₂CF_Three    H Cl H Ph-4-F H
H CH_Three     H NHOCH_Three     H Cl H Ph-2-F H
H CH_Three     H NHOCH_Three     H Cl H Ph-3-F H
H CH_Three     H NHOCH_Three     H Cl H Ph-4-F H
H CH_Three     H NHOCH_Three     H Cl H Ph-2-Cl H
H CH_Three     H NHOCH_Three     H Cl H Ph-3-Cl H
H CH_Three     H NHOCH_Three     H Cl H Ph-4-Cl H
H CH_Three     H NHOCH_Three     H Cl H Ph-2-CH_Three       H
H CH_Three     H NHOCH_Three     H Cl H Ph-3-CH_Three       H
H CH_Three     H NHOCH_Three     H Cl H Ph-4-CH_Three       H
H CH_Three     H NHOCH_Three     H Cl H Ph-2-CF_Three       H
H CH_Three     H NHOCH_Three     H Cl H Ph-3-CF_Three       H
H CH_Three     H NHOCH_Three     H Cl H Ph-4-CF_Three       H
H CH_Three     H NHOCH_Three     H Cl H Ph-2-OCH_Three      H
H CH_Three     H NHOCH_Three     H Cl H Ph-3-OCH_Three      H
H CH_Three     H NHOCH_Three     H Cl H Ph-4-OCH_Three      H
H CH_Three     H NHOCH_Three     H Cl H Ph-4-OCHF₂     H
H CH_Three     H NHOCH_Three     H Cl H Ph-4-OCF_Three      H
H CH_Three     H NHOCH_Three     H Cl H Ph-2,4-F₂      H
H CH_Three     H NHOCH_Three     H Cl H Ph-3,4-F₂      H
H CH_Three     H NHOCH_Three     H Cl H Ph-3-Cl-4-F H
H CH_Three     H NHOCH_Three     H Cl H Ph-2-F-4-Cl H
H CH_Three     H NHOCH_Three     H Cl H Ph-3-F-4-Cl H
H CH_Three     H NHOCH_Three     H Cl H Ph-3,4-Cl₂      H
H CH_Three     H NHOCH_Three     H Cl H Ph-2-F-4-CH_Three     H
H CH_Three     H NHOCH_Three     H Cl H Ph-2-CH_Three-4-Cl H
H CH_Three     H NHOCH_Three     H Cl H Ph-2-F-4-CF_Three     H
H CH_Three     H NHOCH_Three     H Cl H Ph-3-F-4-CF_Three     H
H CH_Three     H NHOCH_Three     H Cl H Ph-2-F-4-OCF_Three    H
H CH_Three     H NHOCH_Three     H Cl H Ph-3-F-4-OCF_Three    H
H CH_Three     H NHOCH_Three     H Cl H T-15 H
H CH_Three     H NHOCH_Three     H Cl H Ph-2,4,5-F_Three     H
H CH_Three     H NHOCH_Three     H Cl H Ph-2,4,6-F_Three     H
H CH_Three     H NHOCH_Three     H Cl H Ph-3,4,5-F_Three     H
H CH_Three     H NHOCH_Three     H Cl H D-1-2a H
H CH_Three     H NHOCH_Three     H Cl H (D-1-2b) -2-CH_Three    H
H CH_Three     H NHOCH_Three     H Cl H (D-2-1b) -5-F H
H CH_Three     H NHOCH_Three     H Cl H (D-8-2b) -2-CH_Three    H
H CH_Three     H NHOCH_Three     H Cl H (D-23-2b) -6-F H
H CH_Three     H NHOCH_Three     H Cl H (D-23-2b) -6-Cl H
H CH_Three     H NHOEt H Cl H Ph-2-F H
H CH_Three     H NHOEt H Cl H Ph-3-F H
H CH_Three     H NHOEt H Cl H Ph-4-F H
H CH_Three     H NHOPr-i H Cl H Ph-2-F H
H CH_Three     H NHOPr-i H Cl H Ph-3-F H
H CH_Three     H NHOPr-i H Cl H Ph-4-F H
H CH_Three     H NHOBu-s H Cl H Ph-2-F H
H CH_Three     H NHOBu-s H Cl H Ph-3-F H
H CH_Three     H NHOBu-s H Cl H Ph-4-F H
H CH_Three     H NHOBu-t H Cl H Ph-2-F H
H CH_Three     H NHOBu-t H Cl H Ph-3-F H
H CH_Three     H NHOBu-t H Cl H Ph-4-F H
H CH_Three     CH_Three      H H Cl H Ph-2-F H
H CH_Three     CH_Three      H H Cl H Ph-3-F H
H CH_Three     CH_Three      H H Cl H Ph-4-F H
H CH_Three     CH_Three      F F Cl H CH_Three         H
H CH_Three     CH_Three      F F Cl H Et H
H CH_Three     CH_Three      F F Cl H n-Pr H
H CH_Three     CH_Three      F F Cl H i-Pr H
H CH_Three     CH_Three      F F Cl H c-Pr H
H CH_Three     CH_Three      F F Cl H T-2 H
H CH_Three     CH_Three      F F Cl H c-Bu H
H CH_Three     CH_Three      F F Cl H t-Bu H
H CH_Three     CH_Three      F F Cl H T-1 H
H CH_Three     CH_Three      F F Cl H CH₂F H
H CH_Three     CH_Three      F F Cl H C (CH_Three)₂F H
H CH_Three     CH_Three      F F Cl H T-4 H
H CH_Three     CH_Three      F F Cl H T-5 H
H CH_Three     CH_Three      F F Cl H T-6 H
H CH_Three     CH_Three      F F Cl H T-7 H
H CH_Three     CH_Three      F F Cl H T-13 H
H CH_Three     CH_Three      F F Cl H CH₂OCH_Three       H
H CH_Three     CH_Three      F F Cl H C (CH_Three)₂OCH_Three     H
H CH_Three     CH_Three      F F Cl H Si (CH_Three)_Three       H
H CH_Three     CH_Three      F F Cl H Ph-2-F H
H CH_Three     CH_Three      F F Cl H Ph-3-F H
H CH_Three     CH_Three      F F Cl H Ph-4-F H
H CH_Three     CH_Three      F F Cl H Ph-2-Cl H
H CH_Three     CH_Three      F F Cl H Ph-3-Cl H
H CH_Three     CH_Three      F F Cl H Ph-4-Cl H
H CH_Three     CH_Three      F F Cl H Ph-2-CH_Three       H
H CH_Three     CH_Three      F F Cl H Ph-3-CH_Three       H
H CH_Three     CH_Three      F F Cl H Ph-4-CH_Three       H
H CH_Three     CH_Three      F F Cl H Ph-2-CF_Three       H
H CH_Three     CH_Three      F F Cl H Ph-3-CF_Three       H
H CH_Three     CH_Three      F F Cl H Ph-4-CF_Three       H
H CH_Three     CH_Three      F F Cl H Ph-2-OCH_Three      H
H CH_Three     CH_Three      F F Cl H Ph-3-OCH_Three      H
H CH_Three     CH_Three      F F Cl H Ph-4-OCH_Three      H
H CH_Three     CH_Three      F F Cl H Ph-4-OCHF₂     H
H CH_Three     CH_Three      F F Cl H Ph-4-OCF_Three      H
H CH_Three     CH_Three      F F Cl H Ph-2,4-F₂      H
H CH_Three     CH_Three      F F Cl H Ph-3,4-F₂      H
H CH_Three     CH_Three      F F Cl H Ph-3-Cl-4-F H
H CH_Three     CH_Three      F F Cl H Ph-2-F-4-Cl H
H CH_Three     CH_Three      F F Cl H Ph-3-F-4-Cl H
H CH_Three     CH_Three      F F Cl H Ph-3,4-Cl₂      H
H CH_Three     CH_Three      F F Cl H Ph-2-F-4-CH_Three     H
H CH_Three     CH_Three      F F Cl H Ph-2-CH_Three-4-Cl H
H CH_Three     CH_Three      F F Cl H Ph-2-F-4-CF_Three     H
H CH_Three     CH_Three      F F Cl H Ph-3-F-4-CF_Three     H
H CH_Three     CH_Three      F F Cl H Ph-2-F-4-OCF_Three    H
H CH_Three     CH_Three      F F Cl H Ph-3-F-4-OCF_Three    H
H CH_Three     CH_Three      F F Cl H T-15 H
H CH_Three     CH_Three      F F Cl H Ph-2,4,5-F_Three     H
H CH_Three     CH_Three      F F Cl H Ph-2,4,6-F_Three     H
H CH_Three     CH_Three      F F Cl H Ph-3,4,5-F_Three     H
H CH_Three     CH_Three      F F Cl H D-1-2a H
H CH_Three     CH_Three      F F Cl H (D-1-2b) -2-CH_Three    H
H CH_Three     CH_Three      F F Cl H (D-2-1b) -5-F H
H CH_Three     CH_Three      F F Cl H (D-8-2b) -2-CH_Three    H
H CH_Three     CH_Three      F F Cl H (D-23-2b) -6-F H
H CH_Three     CH_Three      F F Cl H (D-23-2b) -6-Cl H
H Et H H H Cl H Ph-2-F H
H Et H H H Cl H Ph-3-F H
H Et H H H Cl H Ph-4-F H
H Et H OCH_Three      H Cl H Ph-2-F H
H Et H OCH_Three      H Cl H Ph-3-F H
H Et H OCH_Three      H Cl H Ph-4-F H
H n-Pr H H H Cl H Ph-2-F H
H n-Pr H H H Cl H Ph-3-F H
H n-Pr H H H Cl H Ph-4-F H
H i-Pr H H H Cl H Ph-2-F H
H i-Pr H H H Cl H Ph-3-F H
H i-Pr H H H Cl H Ph-4-F H
H -CH₂CH₂-H H Cl H Ph-2-F H
H -CH₂CH₂-H H Cl H Ph-3-F H
H -CH₂CH₂-H H Cl H Ph-4-F H
H CH₂F H H H Cl H Ph-2-F H
H CH₂F H H H Cl H Ph-3-F H
H CH₂F H H H Cl H Ph-4-F H
H CH₂F H H H Cl H Ph-2-Cl H
H CH₂F H H H Cl H Ph-3-Cl H
H CH₂F H H H Cl H Ph-4-Cl H
H CH₂F H H H Cl H Ph-2-CH_Three       H
H CH₂F H H H Cl H Ph-3-CH_Three       H
H CH₂F H H H Cl H Ph-4-CH_Three       H
H CH₂F H H H Cl H Ph-2-CF_Three       H
H CH₂F H H H Cl H Ph-3-CF_Three       H
H CH₂F H H H Cl H Ph-4-CF_Three       H
H CH₂F H H H Cl H Ph-2-OCH_Three      H
H CH₂F H H H Cl H Ph-3-OCH_Three      H
H CH₂F H H H Cl H Ph-4-OCH_Three      H
H CH₂F H H H Cl H Ph-4-OCHF₂     H
H CH₂F H H H Cl H Ph-4-OCF_Three      H
H CH₂F H H H Cl H Ph-2,4-F₂      H
H CH₂F H H H Cl H Ph-3,4-F₂      H
H CH₂F H H H Cl H Ph-3-Cl-4-F H
H CH₂F H H H Cl H Ph-2-F-4-Cl H
H CH₂F H H H Cl H Ph-3-F-4-Cl H
H CH₂F H H H Cl H Ph-3,4-Cl₂      H
H CH₂F H H H Cl H Ph-2-F-4-CH_Three     H
H CH₂F H H H Cl H Ph-2-CH_Three-4-Cl H
H CH₂F H H H Cl H Ph-2-F-4-CF_Three     H
H CH₂F H H H Cl H Ph-3-F-4-CF_Three     H
H CH₂F H H H Cl H Ph-2-F-4-OCF_Three    H
H CH₂F H H H Cl H Ph-3-F-4-OCF_Three    H
H CH₂F H H H Cl H T-15 H
H CH₂F H H H Cl H Ph-2,4,5-F_Three     H
H CH₂F H H H Cl H Ph-2,4,6-F_Three     H
H CH₂F H H H Cl H Ph-3,4,5-F_Three     H
H CH₂F H H H Cl H D-1-2a H
H CH₂F H H H Cl H (D-1-2b) -2-CH_Three    H
H CH₂F H H H Cl H (D-2-1b) -5-F H
H CH₂F H H H Cl H (D-8-2b) -2-CH_Three    H
H CH₂F H H H Cl H (D-23-2b) -6-F H
H CH₂F H H H Cl H (D-23-2b) -6-Cl H
―――――――――――――――――――――――――――――――――――――――
  The compounds of the present invention include plant diseases and mammals (Mammalia) that occur in vascular plants (Tracheophyta) such as pine (Pinales), magnolias, monocots, and monocots (eudicots), Pathogens of vertebrate (Vertebrata) infections such as birds (Aves), reptiles (Reptilia), and teleosts (Actinopterygii), as well as plant- or animal-parasitic linear animals, bald animals, flat animals, protozoa, etc. Can remove the pests.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

[Formulation Example 1] wettable powder Compound No. 1-019 of the present invention 20 parts Pyrophyllite 74 parts Solpol 5039 4 parts (mixture of nonionic surfactant and anionic surfactant: Toho Chemical Co., Ltd.) Product name)
Carplex # 80D 2 parts (Synthetic hydrous silicic acid: Shionogi & Co., Ltd. trade name)
The above is uniformly mixed and ground to obtain a wettable powder.

[Formulation Example 2] Milk Compound of the present invention No. 3-012 5 parts Xylene 75 parts N-methylpyrrolidone 15 parts Solpol 2680 5 parts (mixture of nonionic surfactant and anionic surfactant: Toho Chemical Industry (Product name)
The above is uniformly mixed to obtain an emulsion.

[Formulation Example 3] Emulsion Invention Compound No. 3-053 4 parts DBE 36 parts (mixture of dimethyl adipate, dimethyl glutarate, dimethyl succinate: trade name, manufactured by INVISTA)
Diisobutyl adipate 30 parts N-methylpyrrolidone 10 parts Soprophor BSU 14 parts (Nonionic surfactant: Rhodia trade name)
Rhodacal 70BC 6 parts (anionic surfactant: Rhodia brand name)
The above is uniformly mixed to obtain an emulsion.

[Composition Example 4] Emulsion Invention Compound No. 7-006 4 parts DBE 11 parts (mixture of dimethyl adipate, dimethyl glutarate, dimethyl succinate: trade name of INVISTA)
Diisobutyl adipate 30 parts N-methylpyrrolidone 5 parts Soprophor BSU 14 parts (Nonionic surfactant: Rhodia trade name)
Rhodacal 70BC 6 parts (anionic surfactant: Rhodia brand name)
Propylene glycol 10 parts Water 20 parts or more are mixed uniformly to make an emulsion.

[Formulation Example 5] Suspension Agent Compound No. 9-003 25 parts Agrisol S-710 10 parts (Nonionic surfactant: Kao Corporation trade name)
LUNOX 1000C 0.5 part (anionic surfactant: Toho Chemical Industries, Ltd. trade name)
Xanthan gum 0.2 parts water 64.3 parts After uniformly mixing the above, wet pulverize to make a suspension.

[Composition Example 6] Granule wettable powder Compound No. 9-004 of the present invention 75 parts Hytenol NE-15 5 parts (anionic surfactant: trade name of Daiichi Kogyo Seiyaku Co., Ltd.)
Vanillex N 10 parts (anionic surfactant: Nippon Paper Industries Co., Ltd. trade name)
Carplex # 80D 10 parts (Synthetic hydrous silicic acid: Shionogi Pharmaceutical Co., Ltd. trade name)
After uniformly mixing and pulverizing the above, a small amount of water is added, stirred and mixed, granulated with an extrusion granulator, and dried to obtain a granulated wettable powder.

[Formulation Example 7] Granules Invention compound No. 3-064 5 parts Bentonite 50 parts Talc 45 parts After uniformly mixing and pulverizing the above, a small amount of water is added and mixed with stirring, and granulated with an extrusion granulator. And dried into granules.

[Composition Example 8] Powder Compound of the present invention No.3-059 3 parts Carplex # 80D 0.5 part (Synthetic hydrous silicic acid: Shionogi Pharmaceutical Co., Ltd. trade name)
Kaolinite 95 parts Diisopropyl phosphate 1.5 parts The above is uniformly mixed and ground to obtain a powder.

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

[Formulation Example 9] wettable powder preparation Compound No. 1-016 of the present invention 25 parts sodium diisobutylnaphthalenesulfonate 1 part calcium n-dodecylbenzenesulfonate 10 parts alkylaryl polyglycol ether 12 parts naphthalenesulfonic acid formalin condensate Sodium salt 3 parts Emulsion type silicone 1 part Silicon dioxide 3 parts Kaolin 45 parts [Formulation Example 10] Water-soluble thickener preparation Compound No. 1-049 20 parts Polyoxyethylene lauryl ether 3 parts Sodium dioctyl sulfosuccinate 3. 5 parts dimethyl sulfoxide 37 parts 2-propanol 36.5 parts [Formulation Example 11] Solution for spraying the present compound No. 1-048 2 parts dimethyl sulfoxide 10 parts 2-propanol 35 parts acetone 53 parts [Formulation Example 12] transdermal Solution for administration Product No. 1-088 5 parts Hexylene glycol 50 parts Isopropanol 45 parts [Formulation Example 13] Solution for transdermal administration Compound No. 3-090 5 parts Propylene glycol monomethyl ether 50 parts Dipropylene glycol 45 parts [Formulation example] 14] Solution for transdermal administration (dropping) The present compound No. 1-087 2 parts light liquid paraffin 98 parts [Formulation example 15] Solution for transdermal administration (dropping) The present compound No. 3-055 2 parts light flow Paraffin 58 parts Olive oil 30 parts ODO-H 9 parts Shin-Etsu Silicone 1 part When using the compound of the present invention as an agricultural or horticultural fungicide or nematode control agent, use an effective amount of the compound of the present invention alone as an active ingredient. If necessary, other fungicides, other nematicides, insecticides, acaricides, plant growth regulators, herbicides, synergists, fertilizers, soil It may be mixed applied at improving agent formulation at or spraying.

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

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

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

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

Insecticides and acaricides:
A: Acetylcholinesterase (AChE) inhibitor Alanicarb, aldicarb, bendiocarb, benfuracarb, butofcarboxim, carbaryl, carbofuran, carbofuran Fan (carbosulfan), ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, pirimicarb, thiodicarb Thiofanox, triazamate,
Acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos ( chlorpyrifos, chlorpyrifos-methyl, cyanophos, diazinon, dichlorvos, dimethoate, dimethylvinphos, disulfoton, EPN, fenitrothion (Fenitrothion), fenthion, isoxathion, malathion, methamidophos, methidathion, omethoate, oxydemeton-methy l), parathion-methyl, phenthoate, phorate, foalone, phosmet, phoxim, pirimiphos-methyl, profenofos , Prothiofos, pyraclofos, sulfopep, terbufos, tetrachlorvinphos, thiometon, trichlorfon,
B: GABAergic chloride channel antagonist endosulfan, alpha-endosulfan,
Ethiprole, fipronil, flufiprole, pyriprole,
Afoxolaner, fluralaner, lotilaner, sarolaner,
C: sodium channel modulators acrinathrin, allethrin, benfluthrin, bifenthrin, kappa-bifenthrin, bioallethrin, bioresmethrin, chloropralethrin ), Cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, cypermethrin ), Alpha-cypermethrin (alpha-cypermethrin), beta-cypermethrin (beta-cypermethrin), zeta-cypermethrin (zeta-cypermethrin), cyphenothrin (cyphenothrin), deltamethrin (deltamethrin) Empenthrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucytrinate, flumethrin, fluvalinate, Tau-fluvalinate, halfenprox, heptafluthrin, hemiprothrin, meperfluthrin, metofluthrin, epsilon-metofluthrin, epsilon-metofluthrin Thrin (momfluorothrin), epsilon-momfluorothrin, permethrin, phenothrin, pyrethrin, resmethrin, silafluophene (Silafluofen), tefluthrin, kappa-tefluthrin, tetramethrin, dT-80-phthalthrin (d-tetramethrin), tetramethylfluthrin, tralomethrin, trans Flutrin, transfluthrin,
Methoxychlor,
D: Nicotinic acetylcholine receptor (nAChR) agonists acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, thiamethoxam
Sulfoxaflor,
Flupyradifurone,
E; nicotinic acetylcholine receptor (nAChR) allosteric modulators spinetoram, spinosad,
F: chloride channel activator abamectin, emamectin-benzoate, lepimectin, milbemectin,
G; juvenile hormone analog mesoprene,
Phenoxycarb,
Pyriproxyfen,
H; Hemiptera selective feeding inhibitor pymetrozine,
Flonicamid,
I; mite growth inhibitor clofentezine, hexythiazox,
Etoxazole,
J: Microbial-derived insect midgut mesentery bacillus thuringiensis (bacillus thuringiensis, subsp.israelensis, subsp.aizawai, subsp.kurstaki, subsp.tenebrionis, etc.)
K; mitochondrial ATP synthase inhibitor diafenthiuron,
Azocyclotin, fenbutatin oxide,
Propargite,
L: oxidative phosphorylation uncoupler, chlorfenapyr,
M; nicotinic acetylcholine receptor (nAChR) channel blocker bensultap, cartap, thiocyclam,
N: chitin biosynthesis inhibitor (type 0)
Bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron ), Nobifluuron, teflubenzuron, triflumuron,
O: Chitin biosynthesis inhibitor (type 1)
Buprofezin,
P: molting inhibitor (fly insect)
Cyromazine,
Q: molting hormone (ecdysone) receptor agonist chromafenozide, halofenozide, methoxyfenozide, tebufenozide, tebufenozide,
R; octopamine receptor agonist amitraz,
S: Mitochondrial electron transport system complex III inhibitor hydramethylnon,
Acequinocyl,
Fluacrypyrim,
T: Mitochondrial electron transport complex I inhibitor fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad, tolfenpyrad,
Rotenone,
U; voltage-gated sodium channel blocker indoxacarb (indoxacarb), indoxacarb-MP (indoxacarb-MP),
Metaflumizone,
V; acetyl CoA carboxylase inhibitor spirodiclofen, spiromesifen, spirotetramat,
W: Mitochondrial electron transport system complex II inhibitor cyenopyrafen, cyflumetofen,
X: Ryanodine receptor modulator chlorantraniliprole, cyantraniliprole, cyclaniliprole, cyhalodiamide, flubendiamide, tetraniliprole,
UN: unknown mechanism of action and other drugs azadirachtin, benzoximate, bifenazate, bromopropylate, dicohol, pyridalyl, pyrifluquinazon,
Afidopyropen, broflanilide, dicloromezotiaz, flometoquin, fluhexafon, fluxametamide, piflubumide, triflumezopyrim (tri), rim 53 NA-89 (test name), NC-515 (test name), and ZDI2501 (test name).

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

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

  Antifungal agents: climbazole, ketoconazole and miconazole nitrate.

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

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

[Synthesis example]
Synthesis example 1
N- [2- [3-Chloro-5-[(4-fluorophenyl) ethynyl] pyridin-2-yl] -2,2-difluoroethyl] -2- (trifluoromethyl) benzamide (Compound No. 1 of the present invention) 1-004).

Step 1; Preparation of 2- (5-Bromo-3-chloropyridin-2-yl) -2,2-difluoroacetonitrile 2- (5-Bromo-3-chloropyridin-2-yl) acetonitrile 2.00 g of tetrahydrofuran To the 40 ml solution, 16 ml of a 1.3M tetrahydrofuran solution of lithium bis (trimethylsilyl) amide was added dropwise with stirring at −78 ° C. After completion of the dropwise addition, the mixture was stirred at the same temperature for 30 minutes. Next, a solution of 6.00 g of N-fluorobenzenesulfonimide in 25 ml of tetrahydrofuran was added dropwise to the reaction mixture. After completion of the addition, stirring was continued for 3 hours at the same temperature. After completion of the reaction, 50 ml of water was added to the reaction mixture and extracted with hexane (50 ml × 3). The organic layers were combined and washed with water (50 ml × 1), dehydrated and dried over saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography {ethyl acetate-hexane [gradient of 0: 100 to 5:95 (volume ratio, the same applies hereinafter)]} to obtain 0.81 g of the desired product as a pale yellow oily substance. Got as.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 8.66 (d, J = 2.1 Hz, 1H), 8.08 (d, J = 2.1 Hz, 1H).

Step 2; Preparation of 2- (5-Bromo-3-chloropyridin-2-yl) -2,2-difluoroethylamine 2- (5-Bromo-3-chloropyridin-2-yl) -2 under nitrogen atmosphere 9 ml of a 1.0M hexane solution of diisobutylaluminum hydride was added dropwise to a solution of 810 mg of 1,2-difluoroacetonitrile in 20 ml of dichloromethane at −78 ° C. with stirring, and the mixture was stirred at the same temperature for 2 hours. Then, 20 ml of a saturated aqueous solution of potassium sodium tartrate (Rochelle salt) and 20 ml of dichloromethane were added to the reaction mixture, and stirring was continued for another 2 hours at room temperature. After completion of the reaction, 30 ml of water was added to the reaction mixture, and the organic layer was separated. The obtained organic layer was washed with a saturated Rochelle salt aqueous solution (20 ml × 1) and then with water (20 ml × 2), and then the solvent was distilled off under reduced pressure. Lastly, 607 mg of the crude target product was obtained as a brown oily substance. This was directly used in the next step without further purification.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.56 (d, J = 2.1 Hz, 1H), 8.00 (d, J = 2.1 Hz, 1H), 3.49 (t, J = 13.8 Hz, 2H) .

Step 3; Preparation of N- [2- (5-Bromo-3-chloropyridin-2-yl) -2,2-difluoroethyl] carbamic acid-tert-butyl 2- (5-Bromo-3-chloropyridine- To a solution of 607 mg of 2-yl) -2,2-difluoroethylamine and 271 mg of triethylamine in 5 ml of dichloromethane was added 584 mg of di-tert-butyl dicarbonate, and the mixture was stirred at room temperature for 2 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography [ethyl acetate-hexane (0:10 to 1: 9 gradient)] to obtain 430 mg of the target product as a pale yellow oil. Obtained as material.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.55 (d, J = 2.1 Hz, 1H), 8.00 (d, J = 2.1 Hz, 1H), 5.05 (bs, 1H), 4.0-4.2 ( m, 2H), 1.40 (s, 9H).

Step 4: Preparation of N- [2- [3-chloro-5-[(4-fluorophenyl) ethynyl] pyridin-2-yl] -2,2-difluoroethyl] carbamic acid-tert-butyl N- [2 -(5-Bromo-3-chloropyridin-2-yl) -2,2-difluoroethyl] carbamic acid-tert-butyl 1.50 g of N, N-dimethylformamide in 4 ml of solution was added 1.64 g of triethylamine, 1- Ethinyl-4-fluorobenzene 631 mg, copper iodide (I) 231 mg and dichlorobis (triphenylphosphine) palladium (II) 283 mg were added, and the mixture was stirred at room temperature for 2 hours under a nitrogen atmosphere. After completion of the reaction, 15 ml of saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate (20 ml × 1). The obtained organic layer was washed with water (10 ml × 2), dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (gradient of 0:10 to 2: 8) to obtain 1.40 g of the objective product as white crystals.
Melting point: 107.0-108.0 ° C
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.57 (d, J = 1.5 Hz, 1H), 7.92 (d, J = 1.5 Hz, 1H), 7.5-7.6 (m, 2H), 7.05- 7.15 (m, 2H), 5.10 (bs, 1H), 4.0-4.2 (m, 2H), 1.41 (s, 9H).

Step 5: Preparation of 2- [3-Chloro-5-[(4-fluorophenyl) ethynyl] pyridin-2-yl] -2,2-difluoroethylamine N- [2- [3-Chloro-5-[( 4-fluorophenyl) ethynyl] pyridin-2-yl] -2,2-difluoroethyl] carbamic acid-tert-butyl To a solution of tert-butyl 1.40 g in dichloromethane 5 ml was added 3 ml of trifluoroacetic acid and stirred at room temperature for 1 hour. did. After completion of the reaction, the solvent was distilled off under reduced pressure, 10 ml of a saturated 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 and washed with water (10 ml × 1), dehydrated and dried over saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 1.01 g of the crude desired product as a brown oily substance. This was directly used in the next step without further purification.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.59 (d, J = 1.5 Hz, 1H), 7.91 (d, J = 1.5 Hz, 1H), 7.5-7.6 (m, 2H), 7.0- 7.15 (m, 2H), 3.4-3.6 (m, 2H).

Step 6: Preparation of N- [2- [3-chloro-5-[(4-fluorophenyl) ethynyl] pyridin-2-yl] -2,2-difluoroethyl] -2- (trifluoromethyl) benzamide 2 -[3-Chloro-5-[(4-fluorophenyl) ethynyl] pyridin-2-yl] -2,2-difluoroethylamine in 90 ml of ethyl acetate in 2 ml of ethyl acetate and 2 ml of 10 wt% aqueous potassium carbonate and 2- (tri 67 mg of fluoromethyl) benzoyl chloride was added and stirred at room temperature for 1 hour. After completion of the reaction, 10 ml of water was added to the reaction mixture and extracted with ethyl acetate (10 ml × 2). The organic layers were combined and washed with water (10 ml × 1), dehydrated and dried over saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography [ethyl acetate-hexane (0:10 to 2: 8 gradient)] to obtain 105 mg of the desired product as white crystals.
Melting point: 164.0 to 166.0 ° C
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.54 (d, J = 1.8 Hz, 1H), 7.95 (d, J = 1.8 Hz, 1H), 7.45-7.7 (m, 6H), 7.0- 7.15 (m, 2H), 6.45 (bs, 1H), 4.4-4.55 (m, 2H).

Synthesis example 2
2-Chloro-N- [2- [3-chloro-5-[(4-fluorophenyl) ethynyl] pyridin-2-yl] -2-fluoropropyl] nicotinamide (present compound No. 3-010).

Step 1; Preparation of 5-bromo-3-chloro-2- (2-methyloxiran-2-yl) pyridine 55% by weight of a solution of 5.2 g of trimethylsulfoxonium iodide in 15 ml of dimethylsulfoxide under ice-cooling and stirring 1.1 g of oily sodium hydride was added and stirred at the same temperature for 30 minutes. The reaction mixture was then added dropwise to a solution of 5.0 g of 1- (5-bromo-3-chloropyridin-2-yl) ethane-1-one in 10 ml of dimethyl sulfoxide under ice-cooling and stirred at room temperature. And stirring was continued for another 15 hours. After completion of the reaction, 20 ml of water was added to the reaction mixture and extracted with ethyl acetate (30 ml × 1). The obtained organic layer was washed with water (30 ml × 1), dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography [ethyl acetate-hexane (0:10 to 3: 7 gradient)] to obtain 5.7 g of the desired product as a brown resinous substance.
¹ H NMR (DMSO-d ₆ , Me ₄ Si, 300 MHz) δ8.66 (d, J = 1.8 Hz, 1H), 8.36 (d, J = 1.8 Hz, 1H), 3.03 (d, J = 5.2 Hz, 1H), 2.92 (d, J = 5.2Hz, 1H), 1.58 (s, 3H).

Step 2: Preparation of N- [2- (5-bromo-3-chloropyridin-2-yl) -2-hydroxypropyl] phthalimide 5-Bromo-3-chloro-2- (2-methyloxiran-2-yl ) To a solution of 5.70 g of pyridine in 40 ml of dimethyl sulfoxide, 4.48 g of potassium phthalimide was added and stirred at 100 ° C. for 6 hours. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, added with 30 ml of water, and extracted with ethyl acetate (20 ml × 2). The organic layers were combined and washed with water (40 ml × 1), dehydrated and dried over saturated brine, then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography [ethyl acetate-hexane (1: 9 to 3: 7 gradient)] to obtain 3.90 g of the desired product as a brown resinous substance.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.3-8.4 (m, 1H), 7.9-7.95 (m, 1H), 7.7-7.8 (m, 2H), 7.65-7.7 (m, 2H) , 5.64 (s, 1H), 4.31 (d, J = 14.0Hz, 1H), 4.21 (d, J = 14.0Hz, 1H), 1.80 (s, 3H).

Step 3: Preparation of N- [2- (5-bromo-3-chloropyridin-2-yl) -2-fluoropropyl] phthalimide N- [2- (5-Bromo-3-chloropyridine] under ice-cooling and stirring -2-yl) -2-hydroxypropyl] phthalimide 2.62 g of bis (2-methoxyethyl) aminosulfur trifluoride was added dropwise to a solution of 3.90 g of dichloromethane in 20 ml of dichloromethane and stirred at 50 ° C. for 12 hours. did. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, 30 ml of saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with dichloromethane (20 ml × 2). The organic layers were combined and washed with water (40 ml × 1), dehydrated and dried over saturated brine, then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was washed with 10 ml of diisopropyl ether to obtain 3.50 g of the desired product as pale yellow crystals.
Melting point 134.0-136.0 ° C
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 8.45-8.55 (m, 1H), 7.85-7.9 (m, 1H), 7.8-7.85 (m, 2H), 7.7-7.8 (m, 2H) , 4.3-4.55 (m, 2H), 1.82 (d, J = 22.4Hz, 3H).

Step 4: Preparation of N- [2- [3-chloro-5-[(4-fluorophenyl) ethynyl] pyridin-2-yl] -2-fluoropropyl] phthalimide N- [2- (5-Bromo-3) -Chloropyridin-2-yl) -2-fluoropropyl] phthalimide in 4 ml of N, N-dimethylformamide in a solution of 762 mg triethylamine, 452 mg 1-ethynyl-4-fluorobenzene, 143 mg copper (I) iodide and 176 mg of dichlorobis (triphenylphosphine) palladium (II) was added, and the mixture was stirred at 60 ° C. for 5 hours under a nitrogen atmosphere. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, 10 ml of saturated aqueous ammonium chloride solution was added, and the mixture was extracted with ethyl acetate (10 ml × 1). The obtained organic layer was washed with water (10 ml × 1), dehydrated and dried over saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography [ethyl acetate-hexane (5: 95-10: 90 gradient)] to obtain 1.2 g of the objective product as brown crystals.
Melting point: 153.0-155.0 ° C
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 8.45-8.55 (m, 1H), 7.8-7.9 (m, 3H), 7.7-7.75 (m, 2H), 7.45-7.6 (m, 2H) , 7.0-7.15 (m, 2H), 4.3-4.6 (m, 2H), 1.86 (d, J = 23.0Hz, 3H).

Step 5; Preparation of 2- [3-Chloro-5-[(4-fluorophenyl) ethynyl] pyridin-2-yl] -2-fluoropropylamine N- [2- [3-Chloro-5-[(4 -Hydrazine monohydrate 432 mg was added to ethanol 4 ml solution of 1.2 g of -fluorophenyl) ethynyl] pyridin-2-yl] -2-fluoropropyl] phthalimide and stirred at 80 ° C. for 5 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, 5 ml of a saturated aqueous sodium hydrogen carbonate solution was added to the residue, and the mixture was extracted with ethyl acetate (10 ml × 2). The organic layers were combined and washed with water (10 ml × 1), dehydrated and dried over saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography [ethyl acetate-hexane (5: 5 to 9: 1 gradient)] to obtain 323 mg of the desired product as a brown resinous substance.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 8.45-8.75 (m, 1H), 7.75-8.05 (m, 1H), 7.45-7.75 (m, 2H), 7.0-7.3 (m, 2H) , 3.05-3.8 (m, 2H), 1.74 (d, J = 23.0Hz, 3H), 1.05-1.45 (m, 2H).

Step 6: Preparation of 2-chloro-N- [2- [3-chloro-5-[(4-fluorophenyl) ethynyl] pyridin-2-yl] -2-fluoropropyl] nicotinamide 2 under ice-cooling and stirring -63 mg of 2-chloronicotinyl chloride was added dropwise to a solution of 100 mg of [3-chloro-5-[(4-fluorophenyl) ethynyl] pyridin-2-yl] -2-fluoropropylamine and 50 mg of triethylamine in 1 ml of dichloromethane. After the dropping, stirring was continued for 1 hour at room temperature. After completion of the reaction, 2 ml of water was added to the reaction mixture and extracted with dichloromethane (5 ml × 1). The obtained organic layer was washed with water (5 ml × 1), dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (2: 8 to 5: 5 gradient) to obtain 69 mg of the objective product as white crystals.
Melting point 149.0-151.0 ° C
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.54 (d, J = 1.7 Hz, 1H), 8.4-8.45 (m, 1H), 8.05-8.1 (m, 1H), 7.86 (d, J = 1.7Hz, 1H), 7.45-7.6 (m, 2H), 7.3-7.35 (m, 1H), 7.2-7.25 (m, 1H), 7.05-7.15 (m, 2H), 4.15-4.4 (m, 2H ), 1.90 (d, J = 21.0Hz, 3H).

Synthesis example 3
N- [2- [3-Chloro-5- (cyclopropylethynyl) pyridin-2-yl] -2,2-difluoro-1-methylethyl] -3- (trifluoromethyl) thiophene-2-carboxamide (this Invention compound No. 7-006).

Step 1; Preparation of 2- (5-bromo-3-chloropyridin-2-yl) -2,2-difluoro-1-methylethylamine 2- (5-Bromo-3) prepared in Step 1 of Synthesis Example 1 -Chloropyridin-2-yl) -2,2-difluoroacetonitrile 1.0 ml of diethyl ether in 5 ml was stirred dropwise with ice-cooling, and 3.1 ml of a 35 wt% diethyl ether solution of methylmagnesium bromide was added dropwise. And stirred for 1 hour. Next, 15 ml of methanol was added to the reaction mixture with stirring under ice cooling, followed by 423 mg of sodium borohydride, and stirring was continued at the same temperature for another hour. After completion of the reaction, the solvent was distilled off under reduced pressure, 10 ml of saturated aqueous ammonium chloride solution was added to the residue, and the mixture was extracted with ethyl acetate (15 ml × 2). The organic layers were combined and washed with water (20 ml × 1), then dehydrated and dried with saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 1.0 g of a crude target product as a brown resinous substance. . This was directly used in the next step without further purification.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.55-8.65 (m, 1H), 7.95-8.0 (m, 1H), 3.7-3.95 (m, 1H), 1.5-1.6 (m, 2H) , 1.23 (d, J = 6.7Hz, 3H).

Step 2; Preparation of N- [2- (5-bromo-3-chloropyridin-2-yl) -2,2-difluoro-1-methylethyl] carbamic acid-tert-butyl 2- (5-bromo-3 -Chloropyridin-2-yl) -2,2-difluoro-1-methylethylamine To 1,05 g of dichloromethane was added di-tert-butyl dicarbonate (895 mg) and triethylamine (566 mg), 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 extracted with dichloromethane (10 ml × 1). The obtained organic layer was washed with water (10 ml × 1), dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography [ethyl acetate-hexane (1: 9 to 3: 7 gradient)] to obtain 1.3 g of the desired product as a brown resinous substance.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.55-8.6 (m, 1H), 7.95-8.0 (m, 1H), 4.5-4.9 (m, 1H), 1.35 (d, J = 7.0Hz , 3H), 1.29 (bs, 9H).

Step 3; Preparation of N- [2- [3-Chloro-5- (cyclopropylethynyl) pyridin-2-yl] -2,2-difluoro-1-methylethyl] carbamic acid-tert-butyl N- [2 -(5-Bromo-3-chloropyridin-2-yl) -2,2-difluoro-1-methylethyl] carbamic acid-tert-butyl in a solution of 1.3 g of N, N-dimethylformamide in 1 ml of triethylamine. 1 g, 493 mg of cyclopropylacetylene, 213 mg of copper (I) iodide and 262 mg of dichlorobis (triphenylphosphine) palladium (II) were added, and the mixture was stirred at room temperature for 18 hours under a nitrogen atmosphere. After completion of the reaction, 10 ml of a saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate (10 ml × 1). The obtained organic layer was washed with water (10 ml × 1), dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography [ethyl acetate-hexane (1: 9 to 3: 7 gradient)] to obtain 750 mg of the desired product as a brown resinous substance.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.4-8.45 (m, 1H), 7.7-7.75 (m, 1H), 7.35-7.4 (m, 1H), 4.6-4.8 (m, 1H) , 1.4-1.5 (m, 1H), 1.33 (d, J = 6.7Hz, 3H), 1.30 (s, 9H), 0.9-1.0 (m, 2H), 0.8-0.9 (m, 2H).

Step 4: Preparation of 2- [3-chloro-5- (cyclopropylethynyl) pyridin-2-yl] -2,2-difluoro-1-methylethylamine N- [2- [3-chloro-5- (cyclo To a solution of 750 mg of propylethynyl) pyridin-2-yl] -2,2-difluoro-1-methylethyl] carbamic acid-tert-butyl in 5 ml of dichloromethane was added 2.5 ml of trifluoroacetic acid and stirred at room temperature for 1 hour. did. After completion of the reaction, the solvent was distilled off under reduced pressure, 10 ml of saturated aqueous sodium hydrogen carbonate solution was added to the residue, and the mixture was extracted with ethyl acetate (10 ml × 2). The organic layers were combined and washed with water (10 ml × 1), then dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 660 mg of the crude desired product as a brown resinous substance. This was directly used in the next step without further purification.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 8.46 (d, J = 1.5 Hz, 1H), 7.74 (d, J = 1.5 Hz, 1H), 3.7-3.9 (m, 1H), 1.5- 1.7 (m, 2H), 1.4-1.55 (m, 1H), 1.21 (d, J = 6.7Hz, 3H), 0.9-1.0 (m, 2H), 0.8-0.9 (m, 2H).

Step 5; N- [2- [3-Chloro-5- (cyclopropylethynyl) pyridin-2-yl] -2,2-difluoro-1-methylethyl] -3- (trifluoromethyl) thiophene-2- Preparation of carboxamide 2- [3-Chloro-5- (cyclopropylethynyl) pyridin-2-yl] -2,2-difluoro-1-methylethylamine 150 mg of N, N-dimethylformamide in 3 ml of solution, 62 mg of triethylamine, N , N-dimethyl-4-aminopyridine 5 mg, 3- (trifluoromethyl) thiophene-2-carboxylic acid 120 mg and 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride 212 mg were added at room temperature. Stir for 16 hours. After completion of the reaction, 10 ml of water was added to the reaction mixture and extracted with ethyl acetate (10 ml × 2). The organic layers were combined and washed with water (10 ml × 1), dehydrated and dried over saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography [ethyl acetate-hexane (3: 7 to 5: 5 gradient)] to obtain 23 mg of the desired product as pale yellow crystals.
Melting point 98.0-101.0 ° C
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.41 (d, J = 1.7 Hz, 1H), 7.76 (d, J = 1.7 Hz, 1H), 7.4-7.5 (m, 1H), 7.35- 7.4 (m, 1H), 6.85-7.05 (m, 1H), 5.1-5.3 (m, 1H), 1.5-1.55 (m, 1H), 1.45 (d, J = 6.8Hz, 3H), 0.9-1.0 ( m, 2H), 0.8-0.9 (m, 2H).

Synthesis example 4
N- [2- [3-Chloro-5- (cyclopropylethynyl) pyridin-2-yl] -2,2-difluoro-1-methylethyl] -N-cyclopropyl-2- (trifluoromethyl) benzamide ( Compound No. 15-001 of the present invention.

Step 1; Production of 1- (5-bromo-3-chloropyridin-2-yl) -1,1-difluoropropan-2-one 2- (5-Bromo-3) produced in Step 1 of Synthesis Example 1 -Chloropyridin-2-yl) -2,2-difluoroacetonitrile 1.0 ml of diethyl ether in 5 ml was stirred dropwise with ice-cooling, and 3.1 ml of 35 wt% diethyl ether solution of methylmagnesium bromide was added dropwise. And stirred for 1 hour. The reaction mixture was then added dropwise to 20 ml of 4M aqueous hydrochloric acid with stirring under ice cooling, and stirring was continued for an additional hour at the same temperature after completion of the dropwise addition. After completion of the reaction, the reaction mixture was extracted with ethyl acetate (15 ml × 1). The obtained organic layer was washed with water (10 ml × 1), dehydrated and dried with saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 920 mg of the crude desired product as a brown oily substance. This was directly used in the next step without further purification.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 8.55 (d, J = 1.8 Hz, 1H), 8.01 (d, J = 1.8 Hz, 1H), 2.47 (s, 3H).

Step 2: Preparation of N- [2- (5-bromo-3-chloropyridin-2-yl) -2,2-difluoro-1-methylethyl] -N-cyclopropylamine 1- (5-Bromo-3 -Chloropyridin-2-yl) -1,1-difluoropropan-2-one To a solution of 920 mg of methanol-acetic acid (10: 1) in 2.2 ml was added 203 mg of cyclopropylamine and stirred at 90 ° C. for 1 hour. did. Next, the reaction mixture was allowed to cool to room temperature, 381 mg of picoline borane complex was added, and stirring was further continued at 90 ° C. for 2 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, 10 ml of saturated aqueous sodium hydrogen carbonate solution was added to the residue, and the mixture was extracted with ethyl acetate (20 ml × 2). The organic layers were combined and washed with water (20 ml × 1), dried over saturated brine, then anhydrous sodium sulfate and dried, and the solvent was distilled off under reduced pressure to obtain 830 mg of the crude desired product as a brown oily substance. This was directly used in the next step without further purification.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.55-8.6 (m, 1H), 7.9-8.0 (m, 1H), 3.6-3.85 (m, 1H), 2.15-2.3 (m, 1H) , 1.65-1.85 (m, 1H), 1.29 (d, J = 7.4Hz, 3H), 0.05-0.55 (m, 4H).

Step 3: Preparation of N- [2- (5-Bromo-3-chloropyridin-2-yl) -2,2-difluoro-1-methylethyl] -N-cyclopropyl-2- (trifluoromethyl) benzamide To a solution of 300 mg of N- [2- (5-bromo-3-chloropyridin-2-yl) -2,2-difluoro-1-methylethyl] -N-cyclopropylamine and 112 mg of triethylamine in 2 ml of dichloromethane, With stirring, 211 mg of 2- (trifluoromethyl) benzoyl chloride was added dropwise and stirred at 40 ° C. for 5 hours. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, 2 ml of water was added, and the mixture was extracted with dichloromethane (10 ml × 1). The obtained organic layer was washed with water (10 ml × 1), dehydrated and dried over saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography [ethyl acetate-hexane (1: 9 to 3: 7 gradient)] to obtain 130 mg of the desired product as a colorless resinous substance.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 8.45-8.7 (m, 1H), 7.9-8.0 (m, 1H), 7.55-7.75 (m, 2H), 7.35-7.55 (m, 2H) , 5.8-6.1 (m, 1H), 2.4-2.65 (m, 1H), 1.56 (d, J = 7.0Hz, 3H), 0.45-0.8 (m, 3H), 0.3-0.45 (m, 1H).

Step 4: N- [2- [3-Chloro-5- (cyclopropylethynyl) pyridin-2-yl] -2,2-difluoro-1-methylethyl] -N-cyclopropyl-2- (trifluoromethyl ) Preparation of benzamide N- [2- (5-Bromo-3-chloropyridin-2-yl) -2,2-difluoro-1-methylethyl] -N-cyclopropyl-2- (trifluoromethyl) benzamide 100 mg To a 1 ml solution of N, N-dimethylformamide was added 61 mg of triethylamine, 26 mg of cyclopropylacetylene, 11 mg of copper (I) iodide and 14 mg of dichlorobis (triphenylphosphine) palladium (II). Stir for hours. After completion of the reaction, 10 ml of a saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate (10 ml × 1). The obtained organic layer was washed with water (10 ml × 1), dehydrated and dried over saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography [ethyl acetate-hexane (1: 9 to 3: 7 gradient)] to obtain 79 mg of the desired product as a brown resinous substance.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 8.45-8.55 (m, 1H), 7.73 (d, J = 1.7Hz, 1H), 7.6-7.65 (m, 1H), 7.35-7.5 (m , 3H), 5.9-6.1 (m, 1H), 2.45-2.6 (m, 1H), 1.55 (d, J = 9.0Hz, 3H), 1.4-1.5 (m, 1H), 0.9-1.05 (m, 2H ), 0.8-0.9 (m, 2H), 0.6-0.7 (m, 2H), 0.25-0.4 (m, 2H).

Synthesis example 5
N- [2- [3-Chloro-5- (cyclopropylethynyl) pyridin-2-yl] -2,2-difluoro-1,1-dimethylethyl] -2- (trifluoromethyl) benzamide (Compound of the present invention) No.1-017).

Step 1; Preparation of 2- (5-bromo-3-chloropyridin-2-yl) -2,2-difluoro-1,1-dimethylethylamine 2- (5-bromo prepared in Step 1 of Synthesis Example 1 To 3 ml of diethyl ether in 423 mg of -3-chloropyridin-2-yl) -2,2-difluoroacetonitrile, 2 ml of 3M diethyl ether solution of methylmagnesium bromide was added dropwise with stirring under ice-cooling, and the mixture was stirred at the same temperature for 30 minutes. did. Next, 568 mg of titanium (IV) tetraisopropoxide was added to the reaction mixture under ice-cooling and stirring was continued at room temperature for another 4 hours. After completion of the reaction, a solution of 300 mg of sodium hydroxide in 10 ml of water was added to the reaction mixture, and extracted with diethyl ether (10 ml × 2). The organic layers were combined and washed with water (20 ml × 1), then dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 534 mg of the crude desired product as a brown oily substance. This was directly used in the next step without further purification.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 8.60 (d, J = 1.8 Hz, 1H), 7.98 (d, J = 1.8 Hz, 1H), 1.29 (s, 6H).

Step 2: Production of N- [2- (5-bromo-3-chloropyridin-2-yl) -2,2-difluoro-1,1-dimethylethyl] -2- (trifluoromethyl) benzamide 2- ( 5-Bromo-3-chloropyridin-2-yl) -2,2-difluoro-1,1-dimethylethylamine was added to a mixed solution of 534 mg of ethyl acetate in 5 ml and potassium carbonate 828 mg in 5 ml of water under ice-cooling and stirring. , 417 mg of 2- (trifluoromethyl) benzoyl chloride was added dropwise and stirred at room temperature for 1 hour. After completion of the reaction, the organic layer was separated, washed with water (10 ml × 1), dehydrated and dried over saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography [ethyl acetate-hexane (5:95 to 15:85 gradient)] to obtain 340 mg of the desired product as a brown resinous substance.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.50 (d, J = 2.1 Hz, 1H), 8.00 (d, J = 2.1 Hz, 1H), 7.4-7.7 (m, 4H), 6.85 ( s, 1H), 1.54 (s, 6H).

Step 3; of N- [2- [3-Chloro-5- (cyclopropylethynyl) pyridin-2-yl] -2,2-difluoro-1,1-dimethylethyl] -2- (trifluoromethyl) benzamide Preparation N- [2- (5-Bromo-3-chloropyridin-2-yl) -2,2-difluoro-1,1-dimethylethyl] -2- (trifluoromethyl) benzamide in a solution of 170 mg of dimethyl sulfoxide in 1 ml 146 mg of triethylamine, 31 mg of cyclopropylacetylene, 20 mg of copper (I) iodide and 25 mg of dichlorobis (triphenylphosphine) palladium (II) were added, and the mixture was stirred at room temperature for 2 hours under a nitrogen atmosphere. After completion of the reaction, 5 ml of saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate (5 ml × 1). The obtained organic layer was washed with water (5 ml × 1), dehydrated and dried over saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography [ethyl acetate-hexane (1: 9 to 3: 7 gradient)] to obtain 41 mg of the desired product as a colorless resinous substance.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 8.35 (d, J = 1.5 Hz, 1H), 7.76 (d, J = 1.5 Hz, 1H), 7.4-7.7 (m, 4H), 7.13 ( bs, 1H), 1.73 (s, 6H), 1.4-1.55 (m, 1H), 0.9-1.0 (m, 2H), 0.8-0.9 (m, 2H).

Synthesis Example 6
N- [2- [3-Chloro-5-[(4-fluorophenyl) ethynyl] pyridin-2-yl] ethyl] -2- (trifluoromethyl) benzamide (the present compound No. 1-019).

Step 1; Preparation of N- [2- (5-Bromo-3-chloropyridin-2-yl) ethyl] carbamic acid-tert-butyl 2- (5-Bromo-3-chloropyridin-2-) under nitrogen atmosphere I) 12 ml of a 1.0 M hexane solution of diisobutylaluminum hydride was added dropwise to a solution of 1.00 g of acetonitrile in 10 ml of dichloromethane over a period of 30 minutes while stirring at -40 ° C. After completion of the dropwise addition, the mixture was stirred for 1 hour at the same temperature. . The reaction mixture was then warmed to room temperature and added dropwise to 50 ml of a saturated aqueous solution of potassium sodium tartrate (Rochelle salt) under ice-cooling. After completion of the addition, stirring was continued for another 1 hour at room temperature. After completion of the reaction, the reaction mixture was extracted with dichloromethane (50 ml × 2), the organic layers were combined, dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure.

The residue was dissolved in 20 ml of dichloromethane, 1.41 g of di-tert-butyl dicarbonate and 0.66 g of triethylamine were added, and the mixture was stirred at room 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 chloroform (20 ml × 1). Left. The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (1: 9-5: 5 gradient) to obtain 615 mg of the desired product as a pale yellow oily substance.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 8.49 (d, J = 1.8 Hz, 1H), 7.82 (d, J = 1.8 Hz, 1H), 5.08 (bs, 1H), 3.5-3.65 ( m, 2H), 3.06 (t, J = 6.0 Hz, 2H), 1.42 (s, 9H).

Step 2: Preparation of N- [2- [3-Chloro-5-[(4-fluorophenyl) ethynyl] pyridin-2-yl] ethyl] carbamic acid-tert-butyl N- [2- (5-Bromo- 3-chloropyridin-2-yl) ethyl] carbamic acid-tert-butyl in a solution of 1.0 g of N, N-dimethylformamide in 1 ml of triethylamine 455 mg, 1-ethynyl-4-fluorobenzene 540 mg, copper (I) iodide 114 mg And dichlorobis (triphenylphosphine) palladium (II) (209 mg) were added, and the mixture was stirred at 80 ° C. for 2 hours under a nitrogen atmosphere. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, 10 ml of saturated aqueous ammonium chloride solution was added, and the mixture was extracted with ethyl acetate (5 ml × 2). The organic layers were combined, dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (0:10 to 1: 9 gradient) to obtain 1.1 g of the objective product as brown crystals.
Melting point: 109.0-111.0 ° C
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.54 (d, J = 1.7 Hz, 1H), 7.76 (d, J = 1.7 Hz, 1H), 7.45-7.55 (m, 2H), 7.0- 7.15 (m, 2H), 5.13 (bs, 1H), 3.55-3.7 (m, 2H), 3.12 (t, J = 6.1Hz, 2H), 1.42 (s, 9H).

Step 3; Preparation of 2- [3-Chloro-5-[(4-fluorophenyl) ethynyl] pyridin-2-yl] ethylamine N- [2- [3-Chloro-5-[(4-fluorophenyl) ethynyl] [Pyridin-2-yl] ethyl] carbamic acid-tert-butyl To a solution of 1.1 g of dichloromethane in 2 ml of dichloromethane was added 2 ml of trifluoroacetic acid and stirred at room temperature for 1 hour. After completion of the reaction, the solvent was distilled off under reduced pressure. To the residue was added 10 ml of saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate (10 ml × 2). The organic layers were combined and washed with water (10 ml × 1), dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 710 mg of the crude target product as dark brown crystals. This was directly used in the next step without further purification.
Melting point 116.0-119.0 ° C.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.5-8.6 (m, 1H), 7.75-7.8 (m, 1H), 7.45-7.55 (m, 2H), 7.0-7.1 (m, 2H) , 3.1-3.35 (m, 2H), 2.3-2.45 (m, 2H).

Step 4; Preparation of N- [2- [3-chloro-5-[(4-fluorophenyl) ethynyl] pyridin-2-yl] ethyl] -2- (trifluoromethyl) benzamide 2- [3-Chloro- To a solution of 200 mg of 5-[(4-fluorophenyl) ethynyl] pyridin-2-yl] ethylamine and 110 mg of triethylamine in 2 ml of dichloromethane was added dropwise 182 mg of 2- (trifluoromethyl) benzoyl chloride with stirring under ice-cooling. The stirring was continued for 1 hour at room temperature. After completion of the reaction, 2 ml of water was added to the reaction mixture and extracted with dichloromethane (5 ml × 1). The organic layer was dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (1: 9 to 3: 7 gradient) to obtain 91 mg of the objective product as yellow crystals.
Melting point 133.0-135.0 ° C
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 8.49 (d, J = 1.7 Hz, 1H), 7.79 (d, J = 1.7 Hz, 1H), 7.45-7.7 (m, 6H), 7.0- 7.1 (m, 2H), 6.65-6.8 (m, 1H), 0.95-4.05 (m, 2H), 3.24 (t, J = 6.1Hz, 2H).

Synthesis example 7
N- [2- [3-Chloro-5-[(4-fluorophenyl) ethynyl] pyridin-2-yl] -2-fluoroethyl] -2- (trifluoromethyl) benzamide (the present compound No. 1- 020).

Step 1; Preparation of 2-bromo-1- (5-bromo-3-chloropyridin-2-yl) ethanol 2-bromo-1- (5-bromo-3-chloropyridin-2-yl) ethanone 2.0 g 266 mg of sodium borohydride was added to a 10 ml methanol solution under ice-cooling and the mixture was stirred at the same temperature for 1 hour. After completion of the reaction, 20 ml of a saturated aqueous ammonium chloride solution was added to the reaction mixture and extracted with ethyl acetate (25 ml × 2). The organic layers were combined and washed with water (20 ml × 1), then dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 1.9 g of a crude desired product as a brown oily substance. This was directly used in the next step without further purification.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.58 (d, J = 1.7 Hz, 1H), 7.90 (d, J = 1.7 Hz, 1H), 5.2-5.3 (m, 1H), 4.36 ( bs, 1H), 3.6-3.9 (m, 1H), 3.15-3.3 (m, 1H).

Step 2: Preparation of N- [2- (5-bromo-3-chloropyridin-2-yl) -2-hydroxyethyl] phthalimide 2-Bromo-1- (5-bromo-3-chloropyridin-2-yl ) 1.17 g of potassium phthalimide was added to 2 ml of dimethyl sulfoxide in 1.90 g of ethanol, and the mixture was stirred at 60 ° C. for 1 hour. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, 15 ml of water was added, and the mixture was extracted with ethyl acetate (15 ml × 1). The organic layer was washed with water (15 ml × 1), dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 0.93 g of the crude desired product as dark brown crystals. This was directly used in the next step without further purification.
Melting point: 146.0-149.0 ° C
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.52 (d, J = 2.1 Hz, 1H), 7.88 (d, J = 2.1 Hz, 1H), 7.8-7.85 (m, 2H), 7.65- 7.8 (m, 2H), 5.3-5.5 (m, 1H), 3.95-4.2 (m, 2H), 1.55-1.8 (m, 1H).

Step 3; Preparation of N- [2- (5-bromo-3-chloropyridin-2-yl) -2-fluoroethyl] phthalimide N- [2- (5-Bromo-3-chloropyridin-2-yl) Bis (2-methoxyethyl) aminosulfur trifluoride (808 mg) was added dropwise to a solution of -2-hydroxyethyl] phthalimide (930 mg) in dichloromethane (3 ml), and the mixture was stirred at 60 ° C. for 3 hours. The reaction mixture was then allowed to cool to room temperature, 540 mg of bis (2-methoxyethyl) aminosulfur trifluoride was added, and the mixture was stirred again at 60 ° C. for 1 hour. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, 15 ml of saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate (15 ml × 1). The organic layer was washed with water (15 ml × 1), dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (1: 9-2: 8 gradient) to obtain 700 mg of the objective product as yellow crystals.
Melting point 153.0-154.0 ° C
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.6-8.65 (m, 1H), 7.9-7.95 (m, 1H), 7.85-7.9 (m, 2H), 7.7-7.8 (m, 2H) 6.17 (ddd, J = 47.0, 8.5, 4.1 Hz, 1H), 4.55-4.7 (m, 1H), 4.0-4.2 (m, 1H).

Step 4: Preparation of N- [2- [3-chloro-5-[(4-fluorophenyl) ethynyl] pyridin-2-yl] -2-fluoroethyl] phthalimide N- [2- (5-Bromo-3) -Chloropyridin-2-yl) -2-fluoroethyl] phthalimide in a solution of 700 mg of N, N-dimethylformamide in 276 mg of triethylamine, 285 mg of 1-ethynyl-4-fluorobenzene, 69 mg of copper (I) iodide and dichlorobis (tri Phenylphosphine) palladium (II) 64 mg was added, and the mixture was stirred at 80 ° C. for 2 hours under a nitrogen atmosphere. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, 10 ml of 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 brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (gradient of 0:10 to 1: 9) to obtain 580 mg of the desired product as brown crystals.
Melting point: 184.0-186.0 ° C
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.65-8.7 (m, 1H), 7.8-7.95 (m, 3H), 7.7-7.8 (m, 2H), 7.5-7.6 (m, 2H) , 7.0-7.15 (m, 2H), 6.22 (ddd, J = 48.7, 8.5, 4.1Hz, 1H), 4.55-4.75 (m, 1H), 4.05-4.25 (m, 1H).

Step 5: Preparation of 2- [3-chloro-5-[(4-fluorophenyl) ethynyl] pyridin-2-yl] -2-fluoroethylamine N- [2- [3-chloro-5-[(4- To a solution of 580 mg of fluorophenyl) ethynyl] pyridin-2-yl] -2-fluoroethyl] phthalimide in 3 ml of ethanol was added 110 mg of hydrazine monohydrate and stirred at room temperature for 2 hours. After completion of the reaction, 5 ml of saturated aqueous sodium hydrogen carbonate 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 brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 300 mg of the crude target product as a yellow resinous substance. This was directly used in the next step without further purification.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.65-8.7 (m, 1H), 7.8-7.85 (m, 1H), 7.5-7.6 (m, 2H), 7.0-7.15 (m, 2H) , 5.85 (ddd, J = 47.8, 7.4, 3.7Hz, 1H), 3.1-3.45 (m, 2H), 1.57 (bs, 2H).

Step 6: Preparation of N- [2- [3-chloro-5-[(4-fluorophenyl) ethynyl] pyridin-2-yl] -2-fluoroethyl] -2- (trifluoromethyl) benzamide 2- [ To a solution of 3-chloro-5-[(4-fluorophenyl) ethynyl] pyridin-2-yl] -2-fluoroethylamine (100 mg) and triethylamine (51 mg) in dichloromethane (2 ml) was added 2- (trifluoromethyl) benzoyl chloride under ice-cooling and stirring. 86 mg was added dropwise, and after completion of the dropwise addition, the mixture was stirred at room temperature for 1 hour. After completion of the reaction, 2 ml of water was added to the reaction mixture and extracted with dichloromethane (5 ml × 1). The organic layer was dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (1: 9 to 3: 7 gradient) to obtain 49 mg of the objective product as pale yellow crystals.
Melting point: 141.0-143.0 ° C
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 8.64 (d, J = 1.7 Hz, 1H), 8.47 (dd, J = 4.8, 1.7 Hz, 1H), 8.12 (dd, J = 8.2, 2.0 Hz, 1H), 7.85-7.9 (m, 1H), 7.5-7.6 (m, 2H), 7.3-7.4 (m, 2H), 7.15-7.2 (m, 1H), 7.05-7.1 (m, 2H), 6.13 (ddd, J = 46.7, 6.5, 4.1Hz, 1H), 4.1-4.45 (m, 2H).

Synthesis example 8
2-Chloro-N- [2- [3-chloro-5-[(4-fluorophenyl) ethynyl] pyridin-2-yl] propyl] nicotinamide (the present compound No. 3-050).

Step 1; Preparation of 2- (5-bromo-3-chloropyridin-2-yl) propanenitrile 2- (5-Bromo-3-chloropyridin-2-yl) acetonitrile 1.50 g of tetrahydrofuran solution in 20 ml Under stirring at 5 ° C., 7 ml of a 1.0M solution of potassium tert-butoxide in tetrahydrofuran was added and stirred at room temperature for 2 hours. Subsequently, 0.97 g of iodomethane was added to the reaction mixture, and stirring was continued for another hour at room temperature. After completion of the reaction, 30 ml of water was added to the reaction mixture and extracted with ethyl acetate (25 ml × 2). The organic layers were combined and washed with water (20 ml × 1), then dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate. Was distilled off. The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (5:95 to 15:85 gradient) to obtain 1.38 g of the desired product as a colorless oil.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.58 (d, J = 2.1 Hz, 1H), 7.88 (d, J = 2.1 Hz, 1H), 4.43 (q, J = 7.2 Hz, 1H) , 1.67 (d, J = 7.2Hz, 3H).

Step 2; Preparation of 2- (5-Bromo-3-chloropyridin-2-yl) -1-propanamine 2- (5-Bromo-3-chloropyridin-2-yl) propanenitrile under nitrogen atmosphere To a 20 g solution of 38 g of dichloromethane, 16 ml of a 1.0 M hexane solution of diisobutylaluminum hydride was added dropwise over 20 minutes with stirring at -40 ° C. After completion of the addition, the mixture was stirred at the same temperature for 1 hour. The reaction mixture was then warmed to room temperature and added dropwise to 50 ml of a saturated aqueous solution of potassium sodium tartrate (Rochelle salt) under ice-cooling. After completion of the addition, stirring was continued for another 1 hour at room temperature. After completion of the reaction, the reaction mixture was extracted with dichloromethane (50 ml × 2), the organic layers were combined and washed with water (20 ml × 1), and then the solvent was distilled off under reduced pressure. The residue was dissolved in 10 ml of ethyl acetate and extracted with 10 ml of 1N aqueous hydrochloric acid. A 10% by weight aqueous sodium hydroxide solution was added to the aqueous layer to adjust the pH to 14, followed by extraction with 30 ml of ethyl acetate. The organic layer was dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 1.04 g of the crude desired product as a reddish brown oily substance. This was directly used in the next step without further purification.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.50 (d, J = 2.1 Hz, 1H), 7.80 (d, J = 2.1 Hz, 1H), 3.35-3.45 (m, 1H), 3.05- 3.15 (m, 1H), 2.85-2.95 (m, 1H), 1.20 (d, J = 6.6Hz, 3H).

Step 3; Preparation of N- [2- (5-Bromo-3-chloropyridin-2-yl) propyl] carbamic acid-tert-butyl 2- (5-Bromo-3-chloropyridin-2-yl) -1 -To a solution of 1.04 g of propanamine and 0.63 g of triethylamine in 10 ml of dichloromethane, 1.08 g of di-tert-butyl dicarbonate was added and stirred at room temperature for 1 hour. After completion of the reaction, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (5:95 to 15:85 gradient) to obtain 1.05 g of the desired product. Obtained as a colorless oil.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.51 (d, J = 1.8Hz, 1H), 7.82 (d, J = 1.8Hz, 1H), 4.86 (bs, 1H), 3.55-3.7 ( m, 1H), 3.4-3.5 (m, 2H), 1.41 (s, 9H), 1.21 (d, J = 7.2Hz, 3H).

Step 4: Preparation of N- [2- [3-Chloro-5-[(4-fluorophenyl) ethynyl] pyridin-2-yl] propyl] carbamic acid-tert-butyl N- [2- (5-Bromo- 3-chloropyridin-2-yl) propyl] carbamic acid-tert-butyl in a solution of 1.0 g of N, N-dimethylformamide in 1 ml of triethylamine 434 mg, 1-ethynyl-4-fluorobenzene 447 mg, copper (I) iodide 109 mg And 100 mg of dichlorobis (triphenylphosphine) palladium (II) were added, and the mixture was stirred at 80 ° C. for 12 hours under a nitrogen atmosphere. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, 10 ml of 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 brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (1: 9 to 2: 8 gradient) to obtain 480 mg of the desired product as a brown resinous substance.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.56 (d, J = 1.8Hz, 1H), 7.96 (d, J = 1.8Hz, 1H), 7.45-7.6 (m, 2H), 6.95- 7.2 (m, 2H), 4.91 (bs, 1H), 3.6-3.75 (m, 1H), 3.50 (t, J = 6.3Hz, 2H), 1.41 (s, 9H), 1.24 (d, J = 6.7Hz , 3H).

Step 5; Preparation of 2- [3-Chloro-5-[(4-fluorophenyl) ethynyl] pyridin-2-yl] -1-propanamine N- [2- [3-Chloro-5-[(4- 1 ml of trifluoroacetic acid was added to 1 ml of a solution of 480 mg of fluorophenyl) ethynyl] pyridin-2-yl] propyl] carbamic acid-tert-butyl and stirred at room temperature for 1 hour. After completion of the reaction, the solvent was distilled off under reduced pressure. To the residue was added 10 ml of saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate (10 ml × 2). The organic layers were combined and washed with water (10 ml × 1), then dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 380 mg of the crude desired product as a brown resinous substance. This was directly used in the next step without further purification.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.55 (d, J = 1.7 Hz, 1H), 7.79 (d, J = 1.7 Hz, 1H), 7.45-7.55 (m, 2H), 7.0- 7.15 (m, 2H), 3.55-3.7 (m, 1H), 3.2-3.35 (m, 1H), 3.05-3.2 (m, 1H), 2.59 (s, 2H), 1.31 (d, J = 7.2Hz, 3H).

Step 6; Preparation of 2-chloro-N- [2- [3-chloro-5-[(4-fluorophenyl) ethynyl] pyridin-2-yl] propyl] nicotinamide 2- [3-chloro-5- [ 88 mg of 2-chloronicotinyl chloride was added to a solution of 120 mg of (4-fluorophenyl) ethynyl] pyridin-2-yl] -1-propanamine and 63 mg of triethylamine in 2 ml of dichloromethane under ice-cooling and stirring. For 1 hour. After completion of the reaction, 2 ml of water was added to the reaction mixture and extracted with dichloromethane (5 ml × 1). The organic layer was dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (1: 9 to 3: 7 gradient) to obtain 74 mg of the objective compound as brown crystals.
Melting point: 129.0-133.0 ° C
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.56 (d, J = 1.7 Hz, 1H), 8.42 (dd, J = 4.8, 2.0 Hz, 1H), 8.09 (dd, J = 7.5, 2.0 Hz, 1H), 7.79 (d, J = 1.7Hz, 1H), 7.45-7.55 (m, 2H), 7.25-7.35 (m, 2H), 7.0-7.1 (m, 2H), 3.8-4.0 (m, 3H), 1.34 (d, J = 6.5Hz, 3H).

Synthesis Example 9
N- [2- [3-Chloro-5-[(4-fluorophenyl) ethynyl] pyridin-2-yl] -2-methylpropyl] -2- (trifluoromethyl) benzamide (the present compound No. 1- 059).

Step 1; Preparation of 2- (5-bromo-3-chloropyridin-2-yl) -2-methylpropanenitrile 2- (5-Bromo-3-chloropyridin-2-yl) acetonitrile 1.50 g of tetrahydrofuran 20 ml To the solution, 13.6 ml of a 1.0M tetrahydrofuran solution of potassium tert-butoxide was added with stirring at −5 ° C., and the mixture was stirred at the same temperature for 10 minutes. Next, 1.94 g of iodomethane was added to the reaction mixture, and stirring was continued for another hour at room temperature. After completion of the reaction, 30 ml of water was added to the reaction mixture and extracted with ethyl acetate (25 ml × 2). The organic layers were combined and washed with water (20 ml × 1), then dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (0:10 to 1: 9 gradient) to obtain 1.61 g of the objective product as a colorless oil.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 8.45 (d, J = 2.0 Hz, 1H), 7.84 (d, J = 2.0 Hz, 1H), 1.76 (s, 6H).

Step 2; Preparation of 2- (5-Bromo-3-chloropyridin-2-yl) -2-methyl-1-propanamine 2- (5-Bromo-3-chloropyridin-2-yl) under nitrogen atmosphere To a solution of 1.61 g of 2-methylpropanenitrile in 15 ml of dichloromethane was added dropwise 18.5 ml of a 1.0 M hexane solution of diisobutylaluminum hydride over 20 minutes with stirring at -40 ° C. And stirred for 15 minutes. After completion of the reaction, 30 ml of water was added dropwise to the reaction mixture and stirred at the same temperature for 30 minutes, then warmed to room temperature, 15 ml of dichloromethane and 6.70 g of potassium sodium tartrate (Rochelle salt) were added, and the mixture was further stirred at room temperature for 3 hours. Continued. The organic layer was separated, and the aqueous layer was extracted with dichloromethane (50 ml × 2). The organic layers were combined and washed with water (20 ml × 1), then dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 1.54 g of the crude desired product as a brown oily substance. This was directly used in the next step without further purification.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.44 (d, J = 2.1 Hz, 1H), 7.74 (d, J = 2.1 Hz, 1H), 3.90 (bs, 2H), 3.10 (s, 2H), 1.44 (s, 6H).

Step 3; Preparation of N- [2- (5-Bromo-3-chloropyridin-2-yl) -2-methylpropyl] carbamic acid-tert-butyl 2- (5-Bromo-3-chloropyridin-2- Yl) -2-methyl-1-propanamine (1.54 g) and triethylamine (1.60 ml) in dichloromethane (15 ml) were added with di-tert-butyl dicarbonate (1.50 g) and stirred at room temperature for 1 hour. After completion of the reaction, 10 ml of water was added to the reaction mixture and extracted with ethyl acetate (20 ml × 2). The organic layers were combined, dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (0: 10-3: 7 gradient) to obtain 911 mg of the desired product as a yellow oily substance.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 8.45 (d, J = 2.0 Hz, 1H), 7.80 (d, J = 2.0 Hz, 1H), 5.41 (bs, 1H), 3.54 (d, J = 6.5Hz, 2H), 1.47 (s, 6H), 1.42 (s, 9H).

Step 4: Preparation of N- [2- [3-chloro-5-[(4-fluorophenyl) ethynyl] pyridin-2-yl] -2-methylpropyl] carbamic acid-tert-butyl N- [2- ( 5-Bromo-3-chloropyridin-2-yl) -2-methylpropyl] carbamic acid-tert-butyl in a solution of 1.0 g of N, N-dimethylformamide in 1 ml of triethylamine 419 mg, 1-ethynyl-4-fluorobenzene 431 mg Then, 105 mg of copper (I) iodide and 97 mg of dichlorobis (triphenylphosphine) palladium (II) were added, and the mixture was stirred at 80 ° C. for 2 hours in a nitrogen atmosphere. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, 10 ml of 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 brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (0:10 to 1: 9 gradient) to obtain 1.0 g of the objective product as brown crystals.
Melting point: 70.0-73.0 ° C
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.51 (d, J = 1.7 Hz, 1H), 7.75 (d, J = 1.7 Hz, 1H), 7.45-7.55 (m, 2H), 7.0- 7.15 (m, 2H), 5.44 (bs, 1H), 3.55 (d, J = 6.8Hz, 2H), 1.48 (s, 6H), 1.42 (s, 9H).

Step 5; Preparation of 2- [3-Chloro-5-[(4-fluorophenyl) ethynyl] pyridin-2-yl] -1-propanamine N- [2- [3-Chloro-5-[(4- To a solution of 1.0 g of fluorophenyl) ethynyl] pyridin-2-yl] -2-methylpropyl] carbamic acid-tert-butyl was added 3 ml of trifluoroacetic acid and stirred at room temperature for 1 hour. After completion of the reaction, the solvent was distilled off under reduced pressure. To the residue was added 10 ml of saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate (10 ml × 2). The organic layers were combined and washed with water (10 ml × 1), then dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 780 mg of the crude desired product as brown crystals. This was directly used in the next step without further purification.
Melting point: 60.0-62.0 ° C
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.51 (d, J = 2.0 Hz, 1H), 7.79 (d, J = 2.0 Hz, 1H), 7.45-7.6 (m, 2H), 7.0- 7.15 (m, 2H), 3.26 (s, 2H), 1.57 (s, 6H).

Step 6: Preparation of N- [2- [3-chloro-5-[(4-fluorophenyl) ethynyl] pyridin-2-yl] -2-methylpropyl] -2- (trifluoromethyl) benzamide 2- [ To a solution of 260 mg of 3-chloro-5-[(4-fluorophenyl) ethynyl] pyridin-2-yl] -1-propanamine and 130 mg of triethylamine in 2 ml of dichloromethane was added 2- (trifluoromethyl) benzoyl chloride under ice-cooling and stirring. 215 mg was added, and after completion of the dropwise addition, the mixture was stirred at room temperature for 1 hour. After completion of the reaction, 2 ml of water was added to the reaction mixture and extracted with dichloromethane (5 ml × 1). The organic layer was dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (1: 9 to 3: 7 gradient) to obtain 218 mg of the desired product as a brown resinous substance.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.44 (d, J = 2.0 Hz, 1H), 7.77 (d, J = 2.0 Hz, 1H), 7.65-7.75 (m, 2H), 7.45- 7.6 (m, 4H), 6.95-7.15 (m, 3H), 3.89 (d, J = 6.5Hz, 2H), 1.58 (s, 6H).

Synthesis Example 10
N-[[1- [3-Chloro-5-[(4-fluorophenyl) ethynyl] pyridin-2-yl] cyclopropyl] methyl] -2- (trifluoromethyl) benzamide (Compound No.1- 060).

Step 1; Preparation of N-[[1- (5-Bromo-3-chloropyridin-2-yl) cyclopropyl] methyl] carbamic acid-tert-butyl
To a solution of 462 mg of [1- (5-bromo-3-chloropyridin-2-yl) cyclopropyl] methylamine and 269 mg of triethylamine in 5 ml of dichloromethane was added 578 mg of di-tert-butyl dicarbonate, 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 extracted with dichloromethane (10 ml × 2). The organic layers were combined, dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (1: 9 to 3: 7 gradient) to obtain 498 mg of the desired product as white crystals.
Melting point 81.0-82.0 ° C
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 8.47 (d, J = 2.1 Hz, 1H), 7.83 (d, J = 2.1 Hz, 1H), 4.78 (bs, 1H), 3.38 (d, J = 6.0Hz, 2H), 1.33 (s, 9H), 0.9-1.05 (m, 4H).

Step 2; Preparation of N-[[1- [3-Chloro-5-[(4-fluorophenyl) ethynyl] pyridin-2-yl] cyclopropyl] methyl] carbamic acid-tert-butyl N-[[1- (5-Bromo-3-chloropyridin-2-yl) cyclopropyl] methyl] carbamic acid-tert-butyl 450 mg of N, N-dimethylformamide in 3 ml solution of triethylamine 380 mg, 1-ethynyl-4-fluorobenzene 224 mg, iodine Copper (I) 71 mg and dichlorobis (triphenylphosphine) palladium (II) 87 mg were added, and the mixture was stirred at 60 ° C. for 3 hours in a nitrogen atmosphere. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, 10 ml of ethyl acetate and 10 ml of saturated aqueous ammonium chloride solution were added, the organic layer was separated, and the aqueous layer was extracted with ethyl acetate (10 ml × 2). The organic layers were combined, dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (gradient of 0: 100 to 15:85) to obtain 407 mg of the objective product as brown crystals.
Melting point: 103.0-104.0 ° C
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.52 (d, J = 1.8 Hz, 1H), 7.77 (d, J = 1.8 Hz, 1H), 7.45-7.55 (m, 2H), 7.0- 7.1 (m, 2H), 4.83 (bs, 1H), 3.41 (d, J = 5.7Hz, 2H), 1.34 (s, 9H), 0.95-1.05 (m, 4H).

Step 3; Preparation of [1- [3-Chloro-5-[(4-fluorophenyl) ethynyl] pyridin-2-yl] cyclopropyl] methylamine N-[[1- [3-Chloro-5-[( To a solution of 4-fluorophenyl) ethynyl] pyridin-2-yl] cyclopropyl] methyl] carbamic acid-tert-butyl in 6 ml of dichloromethane was added 2 ml of trifluoroacetic acid with stirring under ice cooling, and then at room temperature for 1 hour. Stirring was continued. After completion of the reaction, the solvent was distilled off under reduced pressure. To the residue was added 10 ml of saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate (10 ml × 2). The organic layers were combined and washed with water (10 ml × 1), then dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 337 mg of a crude desired product as a brown resinous substance. This was directly used in the next step without further purification.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.55-8.6 (m, 1H), 7.75-7.8 (m, 1H), 7.45-7.55 (m, 2H), 7.0-7.1 (m, 2H) , 2.75-3.25 (m, 2H), 1.47 (bs, 2H), 0.95-1.05 (m, 4H).

Step 4: Preparation of N-[[1- [3-chloro-5-[(4-fluorophenyl) ethynyl] pyridin-2-yl] cyclopropyl] methyl] -2- (trifluoromethyl) benzamide
[1- [3-Chloro-5-[(4-fluorophenyl) ethynyl] pyridin-2-yl] cyclopropyl] methylamine (110 mg) and triethylamine (56 mg) in 2 ml of dichloromethane under ice-cooling and stirring, 2- (trifluoromethyl) ) 99 mg of benzoyl chloride was added dropwise, and after completion of the addition, the mixture was stirred at room temperature for 1 hour. After completion of the reaction, 2 ml of water was added to the reaction mixture and extracted with dichloromethane (5 ml × 1). The organic layer was dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was washed with 10 ml of diisopropyl ether to obtain 107 mg of the desired product as brown crystals.
Melting point 148.0 to 150.0 ° C
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 8.49 (d, J = 1.8 Hz, 1H), 7.81 (d, J = 1.8 Hz, 1H), 7.65-7.7 (m, 2H), 7.45- 7.6 (m, 3H), 7.4-7.45 (m, 1H), 7.0-7.1 (m, 2H), 6.19 (bs, 1H), 3.73 (d, J = 5.1Hz, 2H), 1.05-1.15 (m, 4H).

Synthesis Example 11
N- [2- [3-Chloro-5-[(4-fluorophenyl) ethynyl] pyridin-2-yl] -1-methylethyl] -2- (trifluoromethyl) benzamide (the present compound No. 1- 061).

Step 1; Preparation of 5-bromo-3-chloro-2- (2-nitro-1-propenyl) pyridine A solution of 2.06 g of 5-bromo-3-chloropicolylaldehyde and 1.00 g of 1-butylamine in 10 ml of toluene. While being azeotropically dehydrated using a Dean-Stark tube, the mixture was heated to reflux for 2 hours. Subsequently, the solvent was distilled off under reduced pressure, 10 ml of acetic acid and 1.05 g of nitroethane were added to the residue, and the mixture was stirred at 100 ° C. for 40 minutes. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, 30 ml of water was added and extracted with ethyl acetate (50 ml × 2). The organic layers were combined, dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (3:97) to obtain 0.76 g of the objective product as brown crystals.
Melting point: 44.0-50.0 ° C
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.65 (d, J = 1.8Hz, 1H), 8.25 (s, 1H), 7.96 (d, J = 1.8Hz, 1H), 2.67 and 2.66 ( s, 3H).

Step 2: Preparation of 5-bromo-3-chloro-2- (2-nitropropyl) pyridine 5-Bromo-3-chloro-2- (2-nitro-1-propenyl) pyridine 156 mg in methanol 1.5 ml solution While stirring on ice, 85 mg of sodium borohydride was added and stirred at room temperature for 6 hours. After completion of the reaction, 5 ml of water was added to the reaction mixture and extracted with ethyl acetate (10 ml × 2). The organic layers were combined, dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 120 mg of the crude target product as a yellow resinous substance. This was directly used in the next step without further purification.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 8.38 (d, J = 2.1 Hz, 1H), 7.76 (d, J = 2.1 Hz, 1H), 5.1-5.25 (m, 1H), 3.62 ( dd, J = 16.5, 8.6Hz, 1H), 3.11 (dd, J = 16.5, 5.2Hz, 1H), 1.599 (d, J = 7.0Hz, 3H).

Step 3; Preparation of 2- (5-bromo-3-chloropyridin-2-yl) -1-methylethylamine 120 mg of 5-bromo-3-chloro-2- (2-nitropropyl) pyridine was dissolved in methanol-water (2 1) Dissolved in 3 ml of a mixed solvent, added 138 mg of ammonium chloride and 72 mg of reduced iron, and stirred at 75 ° C. for 16 hours. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, insoluble materials were removed by Celite filtration, and then the solvent was distilled off under reduced pressure. The residue was dissolved in 10 ml of diethyl ether and extracted with 10 ml of 1N aqueous hydrochloric acid. A 1N aqueous sodium hydroxide solution was added to the aqueous layer until pH 14 was reached, followed by extraction with ethyl acetate (30 ml × 2). The organic layers were combined, dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 86 mg of the crude target product as a yellow resinous substance. This was directly used in the next step without further purification.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.50 (d, J = 2.1 Hz, 1H), 7.82 (d, J = 2.1 Hz, 1H), 3.4-3.55 (m, 1H), 2.98 ( dd, J = 14.4, 4.9Hz, 1H), 2.85 (dd, J = 14.2, 8.1Hz, 1H), 1.76 (bs, 2H), 1.18 (d, J = 6.4Hz, 3H).

Step 4: Preparation of N- [2- (5-Bromo-3-chloropyridin-2-yl) -1-methylethyl] carbamic acid-tert-butyl 2- (5-Bromo-3-chloropyridin-2- Yl) To a solution of 86 mg of 1-methylethylamine and 42 mg of triethylamine in 1 ml of dichloromethane was added 91 mg of di-tert-butyl dicarbonate, and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (2: 8 to 4: 6 gradient). Obtained as a substance.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 8.48 (d, J = 2.0 Hz, 1H), 7.81 (d, J = 1.7 Hz, 1H), 4.92 (bs, 1H), 4.0-4.3 ( m, 1H), 2.9-3.2 (m, 2H), 1.36 (s, 9H), 1.21 (d, J = 6.5Hz, 3H).

Step 5: Preparation of N- [2- [3-chloro-5-[(4-fluorophenyl) ethynyl] pyridin-2-yl] -1-methylethyl] carbamic acid-tert-butyl N- [2- ( 5-Bromo-3-chloropyridin-2-yl) -1-methylethyl] carbamic acid-tert-butyl 350 mg of N, N-dimethylformamide in 1 ml solution of triethylamine 152 mg, 1-ethynyl-4-fluorobenzene 156 mg, iodine Copper (I) 38 mg and dichlorobis (triphenylphosphine) palladium (II) 56 mg were added, and the mixture was stirred at 80 ° C. for 2 hours under a nitrogen atmosphere. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, 10 ml of 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 brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (0:10 to 1: 9 gradient) to obtain 260 mg of the objective product as brown crystals.
Melting point 117.0-119.0 ° C.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.54 (d, J = 1.7 Hz, 1H), 7.76 (d, J = 1.7 Hz, 1H), 7.5-7.55 (m, 2H), 7.1- 7.0 (m, 2H), 4.85-5.05 (m, 1H), 4.1-4.3 (m, 1H), 3.09 (d, J = 6.8Hz, 2H), 1.37 (s, 9H), 1.21 (d, J = 6.5Hz, 3H).

Step 6; Preparation of 2- [3-Chloro-5-[(4-fluorophenyl) ethynyl] pyridin-2-yl] -1-methylethylamine N- [2- [3-Chloro-5-[(4- To a solution of 260 mg of fluorophenyl) ethynyl] pyridin-2-yl] -1-methylethyl] carbamic acid-tert-butyl in 2 ml of dichloromethane was added 1 ml of trifluoroacetic acid under ice-cooling and stirring at room temperature for 1 hour. Continued. After completion of the reaction, the solvent was distilled off under reduced pressure. To the residue was added 10 ml of saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate (10 ml × 2). The organic layers were combined and washed with water (10 ml × 1), then dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 250 mg of the crude target product as a brown resinous substance. This was directly used in the next step without further purification.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 8.45-8.5 (m, 1H), 7.8-7.85 (m, 1H), 7.5-7.6 (m, 2H), 7.0-7.1 (m, 2H) , 3.55-3.95 (m, 1H), 3.26 (d, J = 8.5Hz, 2H), 1.65-1.85 (m, 2H), 1.51 (d, J = 6.5Hz, 3H).

Step 7: Preparation of N- [2- [3-chloro-5-[(4-fluorophenyl) ethynyl] pyridin-2-yl] -1-methylethyl] -2- (trifluoromethyl) benzamide 2- [ 2-Chloro-5-[(4-fluorophenyl) ethynyl] pyridin-2-yl] -1-methylethylamine 80 mg and triethylamine 57 mg in 2 ml dichloromethane were stirred with ice cooling and 2- (trifluoromethyl) benzoyl chloride. 87 mg was added dropwise, and after completion of the addition, the mixture was stirred at room temperature for 1 hour. After completion of the reaction, 2 ml of water was added to the reaction mixture and extracted with dichloromethane (5 ml × 1). The organic layer was dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (1: 9 to 3: 7 gradient) to obtain 72 mg of the objective product as pale yellow crystals.
Melting point 139.0-141.0 ° C
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 8.49 (d, J = 1.8 Hz, 1H), 7.80 (d, J = 1.8 Hz, 1H), 7.6-7.7 (m, 1H), 7.4- 7.65 (m, 6H), 7.0-7.1 (m, 2H), 6.7-6.8 (m, 1H), 3.15-3.3 (m, 2H), 1.33 (d, J = 6.7Hz, 3H).

Synthesis Example 12
N- [2- [3-Chloro-5-[(4-fluorophenyl) ethynyl] pyridin-2-yl] -2-methoxy-1-methylethyl] -2- (trifluoromethyl) benzamide (compound of the present invention No.1-066).

Step 1; Preparation of 5-bromo-3-chloro-2- (1-methoxy-2-nitropropyl) pyridine 5-Bromo-3-chloro-2- (2-nitro) prepared in Step 1 of Synthesis Example 11 (1-1) Propenyl) pyridine (760 mg) in toluene (10 ml) was stirred dropwise with ice-cooling, and 28 wt% sodium methoxide methanol solution (2.1 g) was diluted with methanol (3 ml) and added dropwise. Stir for 30 minutes at the same temperature. After completion of the reaction, 1.5 ml of acetic acid and 10 ml of water were added to the reaction mixture, followed by extraction with dichloromethane (30 ml × 1). The organic layer was dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (3:97) to obtain 683 mg of the desired product as a red oily substance.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 8.67 and 8.64 (d, J = 2.1 Hz, 1H), 7.95 and 7.91 (d, J = 2.1 Hz, 1H), 5.35 (d, J = 6.3 Hz, 1H) and 5.30 (d, J = 9.6Hz, 1H), 5.1-5.25 (m, 1H) and 5.04 (qui, J = 6.6Hz, 1H), 3.36 and 3.27 (s, 3H), 1.69 and 1.29 (d, J = 6.9Hz, 3H).

Step 2: Preparation of 2- (5-Bromo-3-chloropyridin-2-yl) -2-methoxy-1-methylethylamine 5-Bromo-3-chloro-2- (1-methoxy-2-nitropropyl) 340 mg of pyridine was dissolved in 4 ml of a methanol-water (1: 1) mixed solvent, 350 mg of ammonium chloride and 182 mg of reduced iron were added, and the mixture was stirred at room temperature for 30 minutes and then at 65 ° C. for 1.5 hours. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, insoluble materials were removed by Celite filtration, and then the solvent was distilled off under reduced pressure. The residue was dissolved in 30 ml of diethyl ether and extracted with 20 ml of a 1% by weight aqueous hydrochloric acid solution. The aqueous layer was made basic by adding 20 ml of a saturated aqueous solution of sodium bicarbonate, and then extracted with 100 ml of ethyl acetate. The organic layer was dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 200 mg of the crude desired product as a brown oily substance. This was directly used in the next step without further purification.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.66 and 8.65 (d, J = 2.1 Hz, 1H), 7.88 and 7.87 (d, J = 2.1 Hz, 1H), 4.58 (d, J = 5.7 Hz, 1H) and 4.46 (d, J = 7.5Hz, 1H), 3.30 and 3.27 (s, 3H), 3.25-3.45 (m, 1H), 1.12 and 0.93 (d, J = 6.6Hz, 3H).

Step 3; Preparation of N- [2- (5-Bromo-3-chloropyridin-2-yl) -2-methoxy-1-methylethyl] carbamic acid-tert-butyl 2- (5-Bromo-3-chloro To a solution of 190 mg of pyridin-2-yl) -2-methoxy-1-methylethylamine and 80 mg of pyridine in 2 ml of dichloromethane was added 178 mg of di-tert-butyl dicarbonate, and the mixture was stirred at room temperature for 30 minutes. After completion of the reaction, 10 ml of water was added to the reaction mixture and extracted with dichloromethane (10 ml × 2). The organic layers were combined, dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (2: 98-20: 80 gradient) to obtain 200 mg of the desired product as a colorless oil.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.65 and 8.59 (d, J = 1.8Hz, 1H), 7.87 and 7.85 (d, J = 1.8Hz, 1H), 5.31 and 4.85 (d, J = 8.1Hz, 1H), 4.75 (d, J = 4.2Hz, 1H) and 4.67 (d, J = 2.4Hz, 1H), 4.0-4.3 (m, 1H), 3.53 (s, 3H), 1.42 and 1.26 (s, 9H), 1.32 and 1.05 (d, J = 6.6 Hz, 3H).

Step 4: Preparation of N- [2- [3-chloro-5-[(4-fluorophenyl) ethynyl] pyridin-2-yl] -2-methoxy-1-methylethyl] carbamic acid-tert-butyl [2- (5-Bromo-3-chloropyridin-2-yl) -2-methoxy-1-methylethyl] carbamic acid-tert-butyl 272 mg of N, N-dimethylformamide in 1 ml solution of triethylamine 109 mg, 1-ethynyl 109 mg of -4-fluorobenzene, 27 mg of copper (I) iodide and 25 mg of dichlorobis (triphenylphosphine) palladium (II) were added, stirred at 80 ° C. for 2 hours under a nitrogen atmosphere, and then dichlorobis (triphenylphosphine) palladium. (II) 42 mg was added, and stirring was further continued for 1 hour. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, 10 ml of 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 brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (0:10 to 1: 9 gradient) to obtain 220 mg of the objective product as a brown resinous substance.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 8.69 and 8.64 (d, J = 2.0 Hz, 1H), 7.80 and 7.78 (d, J = 2.0 Hz, 1H), 7.45-7.55 (m, 2H ), 7.0-7.1 (m, 2H), 5.35-5.5 and 4.85-4.95 (m, 1H), 4.75-4.85 and 4.15-4.3 (m, 1H), 3.36 (s, 3H), 1.43 and 1.29 (s, 9H), 1.32 and 1.06 (d, J = 6.8 Hz, 3H).

Step 5: Preparation of 2- [3-Chloro-5-[(4-fluorophenyl) ethynyl] pyridin-2-yl] -2-methoxy-1-methylethylamine N- [2- [3-Chloro-5- To a solution of 220 mg of [(4-fluorophenyl) ethynyl] pyridin-2-yl] -2-methoxy-1-methylethyl] carbamic acid-tert-butyl in 2 ml of dichloromethane was added 1 ml of trifluoroacetic acid under ice-cooling and stirring. And stirred at room temperature for 1 hour. After completion of the reaction, the solvent was distilled off under reduced pressure, 10 ml of a saturated aqueous sodium hydrogen carbonate solution was added to the residue, and the mixture was extracted with ethyl acetate (10 ml × 2). The organic layers were combined and washed with water (10 ml × 1), then dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 167 mg of the crude target product as a dark brown resinous substance. This was directly used in the next step without further purification.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.7-8.75 (m, 1H), 7.8-7.85 (m, 1H), 7.5-7.55 (m, 2H), 7.0-7.1 (m, 2H) , 4.66 and 4.52 (d, J = 5.5Hz, 1H), 3.35-3.55 (m, 1H), 3.32 and 3.29 (s, 3H), 1.84 and 1.68 (bs, 2H), 1.14 and 0.97 (d, J = 6.5Hz, 3H).

Step 6; N- [2- [3-Chloro-5-[(4-fluorophenyl) ethynyl] pyridin-2-yl] -2-methoxy-1-methylethyl] -2- (trifluoromethyl) benzamide Preparation 2- [3-Chloro-5-[(4-fluorophenyl) ethynyl] pyridin-2-yl] -2-methoxy-1-methylethylamine (80 mg) and triethylamine (38 mg) in dichloromethane (2 ml) under ice-cooling and stirring -(Trifluoromethyl) benzoyl chloride 63mg was dripped, and it stirred at room temperature after completion | finish of dripping for 1 hour. After completion of the reaction, 2 ml of water was added to the reaction mixture and extracted with dichloromethane (5 ml × 1). The organic layer was dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (1: 9 to 3: 7 gradient) to obtain the desired product (125 mg) as a colorless resinous substance.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.64 and 8.62 (d, J = 1.8Hz, 1H), 7.85 and 7.83 (d, J = 1.8Hz, 1H), 7.45-7.75 (m, 6H ), 7.3-7.4 and 7.15-7.25 (m, 1H), 7.0-7.1 (m, 2H), 4.96 and 4.83 (d, J = 4.0Hz, 1H), 4.75-4.9 and 4.55-4.7 (m, 1H) , 3.41 and 3.38 (s, 3H), 1.48 and 1.13 (d, J = 6.7Hz, 3H).

Synthesis Example 13
2-chloro-N- [2- [3-chloro-5-[(4-chloro-2-fluorophenyl) ethynyl] pyridin-2-yl] -2,2-difluoro-1-methylethyl] nicotinamide ( Compound No. 3-089 of the present invention.

Step 1; N- [2- [3-Chloro-5-[(4-chloro-2-fluorophenyl) ethynyl] pyridin-2-yl] -2,2-difluoro-1-methylethyl] carbamic acid-tert -Butyl Production N- [2- (5-Bromo-3-chloropyridin-2-yl) -2,2-difluoro-1-methylethyl] carbamic acid-tert- produced in Step 2 of Synthesis Example 3 1.23 g of butyl, 969 mg of triethylamine, 832 mg of [(4-chloro-2-fluorophenyl) ethynyl] trimethylsilane, 182 mg of copper (I) iodide and 224 mg of dichlorobis (triphenylphosphine) palladium (II) To a 6 ml solution of formamide, 3.8 ml of a 1.0 M tetrahydrofuran solution of tetrabutylammonium fluoride was added and stirred at 70 ° C. for 1.5 hours under a nitrogen atmosphere. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, 10 ml of saturated aqueous ammonium chloride solution and 10 ml of ethyl acetate were added, the organic layer was separated, and the aqueous layer was extracted with ethyl acetate (10 ml × 2). The organic layers were combined and washed with a saturated aqueous ammonium chloride solution (20 ml × 1), then dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (gradient of 0: 100 to 15:85) to obtain 851 mg of the objective product as brown crystals.
Melting point: 127.0-129.0 ° C
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.63 (d, J = 1.8 Hz, 1H), 7.92 (d, J = 1.8 Hz, 1H), 7.47 (dd, J = 8.4, 7.2 Hz, 1H), 7.1-7.2 (m, 2H), 4.7-4.9 (m, 2H), 1.37 (d, J = 6.6Hz, 3H), 1.31 (s, 9H).

Step 2: Preparation of 2- [3-chloro-5-[(4-chloro-2-fluorophenyl) ethynyl] pyridin-2-yl] -2,2-difluoro-1-methylethylamine N under ice-cooling and stirring -[2- [3-chloro-5-[(4-chloro-2-fluorophenyl) ethynyl] pyridin-2-yl] -2,2-difluoro-1-methylethyl] carbamic acid-tert-butyl 830 mg 2 ml of trifluoroacetic acid was added to a 6 ml solution of dichloromethane and stirred at room temperature for 1 hour. After completion of the reaction, the solvent was distilled off under reduced pressure. To the residue was added 10 ml of saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate (10 ml × 2). The organic layers were combined and washed with water (10 ml × 1), then dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 653 mg of the crude desired product as brown crystals. This was directly used in the next step without further purification.
Melting point: 69.0-71.0 ° C
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.6-8.65 (m, 1H), 7.9-7.95 (m, 1H), 7.47 (dd, J = 8.4, 7.2Hz, 1H), 7.15-7.2 (m, 2H), 3.8-3.95 (m, 1H), 1.58 (bs, 2H), 1.25 (d, J = 6.9Hz, 3H).

Step 3; 2-chloro-N- [2- [3-chloro-5-[(4-chloro-2-fluorophenyl) ethynyl] pyridin-2-yl] -2,2-difluoro-1-methylethyl] Preparation of Nicotinamide 2- [3-Chloro-5-[(4-chloro-2-fluorophenyl) ethynyl] pyridin-2-yl] -2,2-difluoro-1-methylethylamine 131 mg of N, N-dimethyl To a solution of formamide 2 ml, triethylamine 111 mg, N, N-dimethyl-4-aminopyridine 9 mg, 2-chloronicotinic acid 69 mg and O- (benzotriazol-1-yl) -N, N, N ′, N′-tetramethyluro 176 mg of nitrotetrafluoroborate was added and stirred at room temperature for 16 hours. After completion of the reaction, 2 ml of water was added to the reaction mixture and extracted with ethyl acetate (5 ml × 2). The organic layers were combined and washed with water (5 ml × 1), then dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (1: 9 to 4: 6 gradient) to obtain 111 mg of the objective product as white crystals.
Melting point: 141.0-147.0 ° C
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.61 (d, J = 1.8 Hz, 1H), 8.45 (dd, J = 4.8, 2.1 Hz, 1H), 7.95-8.0 (m, 2H), 7.46 (dd, J = 8.4, 7.8Hz, 1H), 7.32 (dd, J = 7.5, 4.8Hz, 1H), 7.15-7.2 (m, 2H), 7.04 (d, J = 9.9Hz, 1H), 5.3 -5.4 (m, 1H), 1.52 (d, J = 6.9Hz, 3H).

Synthesis Example 14
N- [2- [3-Chloro-5-[(6-fluoropyridin-3-yl) ethynyl] pyridin-2-yl] -2,2-difluoroethyl] -2- (trifluoromethyl) benzamide (present Invention compound No. 1-011).

Step 1; Preparation of N- [2- [3-chloro-5-[(trimethylsilyl) ethynyl] pyridin-2-yl] -2,2-difluoroethyl] carbamic acid-tert-butyl In Step 3 of Synthesis Example 1 Triethylamine in a solution of N- [2- (5-bromo-3-chloropyridin-2-yl) -2,2-difluoroethyl] carbamic acid-tert-butyl 1.86 g of N-N-dimethylformamide 15 ml 1.52 g, 0.59 g of trimethylsilylacetylene, 285 mg of copper (I) iodide and 350 mg of dichlorobis (triphenylphosphine) palladium (II) were added, and the mixture was stirred at room temperature for 1 hour in a nitrogen atmosphere. After completion of the reaction, 20 ml of a saturated aqueous ammonium chloride solution and 20 ml of ethyl acetate were added to the reaction mixture, the organic layer was separated, and the aqueous layer was extracted with ethyl acetate (10 ml × 2). The organic layers were combined and washed with 20 ml of a saturated aqueous ammonium chloride solution, dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (0:10 to 2: 8 gradient) to obtain 1.44 g of the objective product as yellow crystals.
Melting point 93.0-97.0 ° C
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.50 (d, J = 1.5Hz, 1H), 7.85 (d, J = 1.5Hz, 1H), 5.08 (bs, 1H), 4.07 (td, J = 12.9, 6.6Hz, 2H), 1.41 (s, 9H), 0.27 (s, 9H).

Step 2: Preparation of N- [2- [3-Chloro-5-[(6-fluoropyridin-3-yl) ethynyl] pyridin-2-yl] -2,2-difluoroethyl] carbamic acid-tert-butyl N- [2- [3-Chloro-5-[(trimethylsilyl) ethynyl] pyridin-2-yl] -2,2-difluoroethyl] carbamic acid-tert-butyl 480 mg, triethylamine 375 mg, 2-fluoro-5-iodo To a solution of 303 mg of pyridine, 71 mg of copper (I) iodide and 87 mg of dichlorobis (triphenylphosphine) palladium (II) in 6 ml of N, N-dimethylformamide was added 1.3 ml of a 1.0 M tetrahydrofuran solution of tetrabutylammonium fluoride. The mixture was stirred at room temperature for 16 hours under a nitrogen atmosphere. After completion of the reaction, 10 ml of a saturated aqueous ammonium chloride solution and 10 ml of ethyl acetate were added to the reaction mixture, the organic layer was separated, and the aqueous layer was extracted with ethyl acetate (10 ml × 2). The organic layers were combined and washed with 20 ml of a saturated aqueous ammonium chloride solution, then dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (0:10 to 2: 8 gradient) to obtain 324 mg of the desired product as a colorless resin substance.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.55-8.65 (m, 1H), 8.4-8.5 (m, 1H), 7.9-8.0 (m, 2H), 6.95-7.05 (m, 1H) , 5.05-5.2 (m, 1H), 4.0-4.2 (m, 2H), 1.41 (s, 9H).

Step 3; Preparation of 2- [3-chloro-5-[(6-fluoropyridin-3-yl) ethynyl] pyridin-2-yl] -2,2-difluoroethylamine N- [2- under ice-cooling stirring [3-Chloro-5-[(6-fluoropyridin-3-yl) ethynyl] pyridin-2-yl] -2,2-difluoroethyl] carbamic acid-tert-butyl 324 mg in dichloromethane 3 ml solution in trifluoroacetic acid 1 ml And stirred at room temperature for 1 hour. After completion of the reaction, the solvent was distilled off under reduced pressure, 10 ml of saturated aqueous sodium hydrogen carbonate solution was added to the residue, and the mixture was extracted with ethyl acetate (10 ml × 2). The organic layers were combined and washed with water (10 ml × 1), then dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 253 mg of the crude desired product as yellow crystals. This was directly used in the next step without further purification.
Melting point: 109.0-111.0 ° C
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.61 (d, J = 1.2 Hz, 1H), 8.43 (d, J = 2.4 Hz, 1H), 7.9-8.0 (m, 2H), 7.00 ( dd, J = 8.4, 3.0 Hz, 1H), 3.52 (t, J = 14.1 Hz, 2H), 1.58 (bs, 2H).

Step 4; N- [2- [3-Chloro-5-[(6-fluoropyridin-3-yl) ethynyl] pyridin-2-yl] -2,2-difluoroethyl] -2- (trifluoromethyl) Preparation of benzamide 119 mg of 2- [3-chloro-5-[(6-fluoropyridin-3-yl) ethynyl] pyridin-2-yl] -2,2-difluoroethylamine and 77 mg of tritylamine under ice-cooling and stirring To the 2 ml solution, 88 mg of 2- (trifluoromethyl) benzoyl chloride was added dropwise, and after completion of the addition, the mixture was stirred at room temperature for 16 hours. After completion of the reaction, 2 ml of water was added to the reaction mixture, the organic layer was separated, and the aqueous layer was extracted with dichloromethane (5 ml × 1). The organic layers were combined and washed with water (10 ml × 1), then dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The remaining solid was washed with 10 ml of diisopropyl ether to obtain 148 mg of the desired product as white crystals.
Melting point: 155.0-157.0 ° C
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.55-8.6 (m, 1H), 8.4-8.45 (m, 1H), 7.97 (d, J = 1.8Hz, 1H), 7.93 (ddd, J = 8.7, 7.5, 2.4Hz, 1H), 7.5-7.7 (m, 4H), 6.99 (ddd, J = 8.7, 3.3, 0.9Hz, 1H), 6.42 (t, J = 6.6Hz, 1H), 4.47 ( td, J = 13.5, 6.6Hz, 2H).

  This invention compound can be manufactured according to the said manufacturing method and an Example. Examples of alkynylpyridine-substituted amide compounds included in the present invention produced in the same manner as in Synthesis Examples 1 to 14 are shown in Tables 3 to 17, and further examples of production intermediates are shown in Tables 18 to As shown in Table 20, the alkynylpyridine-substituted amide compounds and their production intermediates encompassed by the present invention are not limited to these.

In the table, c-Pr represents a cyclopropyl group, Bu-t represents a tert-butyl group, Ph represents a phenyl group, 1-Naph represents a 1-naphthyl group, and 2-Naph represents a 2-naphthyl group. Represent,
In the table, the aromatic heterocycles represented by D-1-2a to D-25-3a each represent the following structure,

The number representing the substitution position of the substituent (Z) _n corresponds to the position of the number described in the above structural formula. For example, in the table, “(D-23-2b) -6-F” The description represents “6-fluoropyridin-3-yl group”.

  In the table, T-15 represents the following structure.

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

――――――――――――――――――――――――――――――――――――――――
No. X ¹ R ³ R ⁴ R ¹ R ² Y ¹ R ⁶ mp (℃)
――――――――――――――――――――――――――――――――――――――――
1-001 CF ₃ HHFF Cl Ph-2-F 177.0-178.0
1-002 CF ₃ HHFF Cl Ph-3-F 145.0-147.0
1-003 IHHFF Cl Ph-4-F 163.0-166.0
1-004 CF ₃ HHFF Cl Ph-4-F 164.0-166.0
1-005 CF ₃ HHFF Cl Ph-2-CF ₃ 92.0-94.0
1-006 CF ₃ HHFF Cl Ph-3-CF ₃ 119.0-121.0
1-007 CF ₃ HHFF Cl Ph-4-CF ₃ 148.0-150.0
1-008 CF ₃ HHFF Cl Ph-4-CN 178.0-180.0
1-009 CF ₃ HHFF Cl D-2-2a 176.0-178.0
1-010 CF ₃ HHFF Cl D-23-2a 190.0-191.0
1-011 CF ₃ HHFF Cl (D-23-2b) -6-F 155.0-157.0
1-012 CF ₃ HHFF Cl D-23-3a * 1
1-013 CF ₃ HH CH ₃ F Cl Ph-4-F 146.0-149.0
1-014 CF ₃ CH ₃ HFF Cl c-Pr 126.0-129.0
1-015 CF ₃ CH ₃ HFF Cl Ph-4-F 178.0-180.0
1-016 CF ₃ CH ₃ HFF Cl Ph-4-Cl 162.0-163.0
1-017 CF ₃ CH ₃ CH ₃ FF Cl c-Pr * 1
1-018 CF ₃ CH ₃ CH ₃ FF Cl Ph-4-F * 1
1-019 CF ₃ HHHH Cl Ph-4-F 133.0-135.0
1-020 CF ₃ HHFH Cl Ph-4-F 141.0-143.0
1-021 CF ₃ HHFF Cl Ph-2-Cl 173.0-174.0
1-022 CF ₃ HHFF Cl Ph-3-Cl 142.0-145.0
1-023 CF ₃ HHFF Cl Ph-4-Cl 148.0-151.0
1-024 CF ₃ HHFF Cl Ph-4-Br 174.5-176.5
1-025 Cl HHFF Cl Ph-2-CH ₃ 124.5-128.5
1-026 CH ₃ HHFF Cl Ph-2-CH ₃ 118.0-120.0
1-027 CF ₃ HHFF Cl Ph-2-CH ₃ 141.0-143.0
1-028 CF ₃ HHFF Cl Ph-3-CH ₃ 136.0-139.0
1-029 NO ₂ HHFF Cl Ph-3-CH ₃ 183.0-184.0
1-030 CF ₃ HHFF Cl Ph-4-CH ₃ 184.0-186.0
1-031 CF ₃ HHFF Cl Ph-4-Bu-t * 1
1-032 SO ₂ CH ₃ HHFF Cl Ph-4-Bu-t 188.0-189.0
1-033 Br HHFF Cl Ph-2-OCH ₃ 132.0-134.0
1-034 CF ₃ HHFF Cl Ph-2-OCH ₃ 125.0-128.0
1-035 CF ₃ HHFF Cl Ph-3-OCH ₃ * 1
1-036 CF ₃ HHFF Cl Ph-4-OCH ₃ 154.0-157.0
1-037 CF ₃ HHFF Cl Ph-4-OCHF ₂ 133.0-137.0
1-038 CF ₃ HHFF Cl Ph-4-OCF ₃ 111.0-114.0
1-039 CF ₃ HHFF Cl Ph-4-SCH ₃ 152.0-155.0
1-040 CF ₃ HHFF Cl Ph-4-S (O) CH ₃ 204.0-205.0
1-041 CF ₃ HHFF Cl Ph-4-SO ₂ CH ₃ 209.0-211.0
1-042 CF ₃ HHFF Cl Ph-4-SCF ₃ 134.0-136.0
1-043 CF ₃ HHFF Cl Ph-4-NO ₂ 171.0-172.0
1-044 CF ₃ HHFF Cl Ph-2,4-F ₂ 139.0-141.5
1-045 CF ₃ HHFF Cl Ph-3,4-F ₂ 136.5-139.5
1-046 CF ₃ HHFF Cl Ph-3,5-F ₂ 133.5-136.0
1-047 CF ₃ HHFF Cl Ph-3-Cl-4-F 141.5-142.5
1-048 CF ₃ HHFF Cl Ph-2-F-4-Cl 151.5-152.5
1-049 CF ₃ HHFF Cl Ph-3-F-4-Cl 132.0-134.0
1-050 CF ₃ HHFF Cl Ph-3,4-Cl ₂ 127.5-130.5
1-051 CF ₃ HHFF Cl Ph-3-F-4-OCF ₃ 125.0-127.0
1-052 CF ₃ HHFF Cl Ph-3,4,5-F ₃ 122.0-124.0
1-053 CF ₃ HHFF Cl D-1-2a 169.0-172.0
1-054 CF ₃ HHFF Cl D-2-1a 149.0-151.0
1-055 CF ₃ HHFF Cl (D-8-2b) -2-CH ₃ 142.0-144.0
1-056 CF ₃ HHFF Cl (D-23-2b) -6-Cl 137.0-139.0
1-057 CF ₃ HHFF Cl (D-23-3b) -2-F 132.0-134.0
1-058 CF ₃ HH CH ₃ H Cl Ph-4-F 168.0-170.0
1-059 CF ₃ HH CH ₃ CH ₃ Cl Ph-4-F * 1
1-060 CF ₃ HH -CH ₂ CH ₂ -Cl Ph-4-F 148.0-150.0
1-061 CF ₃ CH ₃ HHH Cl Ph-4-F 139.0-141.0
1-062 CF ₃ CH ₃ HFF Cl C (CH ₃ ) ₂ F * 1
1-063 CF ₃ CH ₃ HFF Cl Ph-4-CF ₃ 161.0-165.0
1-064 CF ₃ CH ₃ HFF Cl Ph-4-OCH ₃ * 1
1-065 CF ₃ CH ₃ HFF Cl Ph-4-CN 171.0-173.0
1-066 CF ₃ CH ₃ H OCH ₃ H Cl Ph-4-F * 1
1-067 CF ₃ HHHH Cl Ph-2-F 137.0-139.0
1-068 CF ₃ HHHH Cl Ph-4-Cl 147.0-149.0
1-069 CF ₃ HHHH Cl Ph-4-CF ₃ 156.0-159.0
1-070 CF ₃ HHHH Cl Ph-2-F-4-Cl 147.0-149.0
1-071 CF ₃ HHFH Cl Ph-2-F-4-Cl 147.0-150.0
1-072 CF ₃ HHFF Cl Ph-2-F-4-CH ₃ 178.0-180.0
1-073 CF ₃ HHFF Cl Ph-3-CF ₃ -4-Cl 147.0-149.0
1-074 CF ₃ HHFF Cl (D-1-2b) -2-CH ₃ * 1
1-075 CF ₃ HHFF Cl (D-2-2b) -5-CH ₃ 164.0-165.0
1-076 CF ₃ HHFF Cl (D-6-1a) -1-CH ₃ 166.0-167.0
1-077 Cl HHFF Cl D-23-1a 151.0-153.0
1-078 CF ₃ HHFF Cl D-23-1a 157.0-160.0
1-079 Cl HHFF Cl (D-23-2b) -6-CF ₃ 133.0-137.0
1-080 CF ₃ HHFF Cl (D-23-2b) -6-CF ₃ 153.0-157.0
1-081 CF ₃ HHFF Cl (D-23-3b) -3-F 130.0-132.0
1-082 Cl HHFF Cl D-25-1a 154.0-155.0
1-083 CF ₃ HHFF Cl D-25-1a 174.0-176.0
1-084 Cl HHFF Cl D-25-3a 154.0-159.0
1-085 CF ₃ HHFF Cl D-25-3a 165.0-170.0
1-086 CF ₃ HH CH ₃ H Cl Ph-2-F 89.0-91.0
1-087 CF ₃ CH ₃ HFF Cl Ph-2-F-4-Cl 149.0-151.0
1-088 CF ₃ CH ₃ HFF Cl Ph-3-F-4-Cl 160.0-161.0
1-089 CF ₃ CH ₃ HFF Cl (D-23-2b) -6-F 155.0-157.0
1-090 IHHHH Cl Ph-3-F 160.0-162.0
1-091 CF ₃ HHHH Cl Ph-3-F 150.0-152.0
1-092 CF ₃ HHFF Cl Ph-4-S (O) CF ₃ 160.0-162.0
1-093 CF ₃ HHFF Cl Ph-4-SO ₂ CF ₃ 102.0-105.0
1-094 CF ₃ HHFF Cl Ph-2,4-Cl ₂ 153.0-154.0
1-095 CF ₃ HHFF Cl Ph-2-CH ₃ -4-F 149.0-150.0
1-096 CF ₃ HHFF Cl Ph-2-CH ₃ -4-Cl 149.0-150.0
1-097 CF ₃ HHFF Cl Ph-2-CF ₃ -4-F 151.0-153.0
1-098 CF ₃ HHFF Cl Ph-2-F-3-CF ₃ 147.0-150.0
1-099 CF ₃ HHFF Cl Ph-3-CF ₃ -4-F 143.0-144.0
1-100 CF ₃ HHFF Cl Ph-2-F-4-CF ₃ 142.5-143.5
1-101 CF ₃ HHFF Cl Ph-3-OCH ₃ -4-F 164.0-166.0
1-102 CF ₃ HHFF Cl Ph-2-F-4-OCH ₃ 169.0-171.0
1-103 CF ₃ HHFF Cl Ph-3-OCH ₃ -4-Cl 165.0-166.0
1-104 CF ₃ HHFF Cl Ph-2-F-4-OCF ₃ 127.0-129.0
1-105 IHHFF Cl Ph-3-F-4-OCF ₃ 150.0-153.0
1-106 CF ₃ HHFF Cl T-15 141.0-145.0
1-107 CF ₃ HHFF Cl Ph-2,4,5-F ₃ 121.0-122.0
1-108 CF ₃ HHFF Cl Ph-2,4,6-F ₃ 154.0-156.0
1-109 Cl HHFF Cl Ph-3,4,5-F ₃ 121.0-123.0
1-110 CF ₃ HHFF Cl Ph-2,6-F ₂ -4-Cl 191.0-195.0
1-111 CF ₃ HHFF Cl 2-Naph 194.0-196.0
1-112 CF ₃ HHFF Cl (D-2-2b) -2-CH ₃ -5-Cl 146.0-148.0
1-113 CF ₃ HHFF Cl (D-23-1b) -3,5-Cl ₂ 156.0-157.0
1-114 CF ₃ HH -CH ₂ CH ₂ -Cl Ph-4-Cl 145.0-147.0
1-115 CF ₃ CH ₃ HFF Cl Ph-2-F 150.0-152.0
1-116 CF ₃ CH ₃ HFF Cl Ph-2,4-F ₂ 145.0-147.0
1-117 CF ₃ CH ₃ HFF Cl Ph-3,4-F ₂ * 1
1-118 CF ₃ CH ₃ HFF Cl Ph-3,4-Cl ₂ 162.0-164.0
1-119 CF ₃ CH ₃ HFF Cl Ph-2-F-4-CH ₃ 141.0-144.0
1-120 CF ₃ CH ₃ HFF Cl Ph-2-CH ₃ -4-Cl 146.0-148.0
1-121 CF ₃ CH ₃ HFF Cl Ph-2-F-4-CF ₃ 141.0-143.0
1-122 CF ₃ CH ₃ HFF Cl Ph-3-OCH ₃ -4-Cl 168.0-170.0
1-123 CF ₃ CH ₃ HFF Cl Ph-2,4,6-F ₃ 145.0-148.0
1-124 CF ₃ CH ₃ HFF Cl Ph-3,4,5-F ₃ 140.0-142.0
1-125 CF ₃ CH ₃ HFF Cl (D-23-2b) -6-Cl 165.0-166.0
――――――――――――――――――――――――――――――――――――――――
Table 4

――――――――――――――――――――――――――――――――――――――――
No. X ¹ R ³ R ⁴ R ¹ R ² Y ¹ R ⁶ mp (℃)
――――――――――――――――――――――――――――――――――――――――
2-001 CF ₃ HHFF Cl Ph-4-F * 1
2-002 Cl CH ₃ HFF Cl Ph-4-Cl * 1
2-003 Cl HHFF Cl Ph-4-F 142.0-146.0
2-004 CF ₃ HHFF Cl Ph-4-Br 150.5-152.0
2-005 CF ₃ HHFF Cl Ph-4-OCHF ₂ 135.5-137.5
2-006 CF ₃ HHFF Cl Ph-4-S (O) CH ₃ 178.5-179.5
2-007 CF ₃ HHFF Cl Ph-4-SCF ₃ 115.0-119.0
2-008 Cl HHHH Cl Ph-2-F 107.0-111.0
2-009 Cl HHHH Cl Ph-4-Cl 140.0-141.0
2-010 CF ₃ HHHH Cl Ph-4-CF ₃ 140.0-146.0
2-011 CF ₃ HHHH Cl Ph-2-F-4-Cl 133.0-135.0
2-012 CF ₃ HHFH Cl Ph-2-F-4-Cl 153.0-155.0
2-013 Cl HHFF Cl Ph-3-CF ₃ -4-Cl 121.0-124.0
2-014 Cl HHFF Cl (D-2-2b) -5-CH ₃ 151.0-155.0
2-015 Cl HH CH ₃ H Cl Ph-2-F * 1
2-016 CF ₃ CH ₃ HFF Cl Ph-4-Cl 109.0-112.0
2-017 Cl CH ₃ HFF Cl Ph-2-F-4-Cl 124.0-127.0
2-018 CF ₃ CH ₃ HFF Cl Ph-2-F-4-Cl 130.0-132.0
2-019 Cl CH ₃ HFF Cl Ph-3-F-4-Cl 126.0-128.0
2-020 CF ₃ CH ₃ HFF Cl Ph-3-F-4-Cl 142.0-144.0
2-021 Cl HHFF Cl Ph-4-Cl 155.0-156.0
2-022 CF ₃ HHFF Cl Ph-4-Cl 142.0-143.0
2-023 Cl HHFF Cl Ph-4-CF ₃ 153.0-155.0
2-024 CF ₃ HHFF Cl Ph-4-CF ₃ 172.5-173.5
2-025 CF ₃ HHFF Cl Ph-4-S (O) CF ₃ 129.0-131.0
2-026 CF ₃ HHFF Cl Ph-4-SO ₂ CF ₃ 159.0-161.0
2-027 Cl HHFF Cl Ph-2-F-4-Cl 132.0-133.0
2-028 CF ₃ HHFF Cl Ph-2-F-4-Cl 146.0-148.0
2-029 CF ₃ HHFF Cl Ph-2,4-Cl ₂ 157.0-159.0
2-030 Cl HHFF Cl Ph-3,4-Cl ₂ 166.0-167.0
2-031 CF ₃ HHFF Cl Ph-3,4-Cl ₂ 145.0-148.0
2-032 CF ₃ HHFF Cl Ph-2-CH ₃ -4-F 111.0-115.0
2-033 CF ₃ HHFF Cl Ph-2-F-4-CH ₃ 154.0-156.0
2-034 CF ₃ HHFF Cl Ph-2-CH ₃ -4-Cl 151.5-153.0
2-035 CF ₃ HHFF Cl Ph-2-CF ₃ -4-F 145.0-148.0
2-036 CF ₃ HHFF Cl Ph-2-F-3-CF ₃ 164.0-165.0
2-037 CF ₃ HHFF Cl Ph-3-CF ₃ -4-F 139.0-140.0
2-038 CF ₃ HHFF Cl Ph-2-F-4-CF ₃ 150.0-152.0
2-039 CF ₃ HHFF Cl Ph-3-OCH ₃ -4-F 160.0-162.0
2-040 CF ₃ HHFF Cl Ph-2-F-4-OCH ₃ 139.0-141.0
2-041 CF ₃ HHFF Cl Ph-3-OCH ₃ -4-Cl 181.0-183.0
2-042 CF ₃ HHFF Cl Ph-2-F-4-OCF ₃ 137.0-139.0
2-043 CF ₃ HHFF Cl Ph-3-F-4-OCF ₃ 126.0-129.0
2-044 CF ₃ HHFF Cl T-15 125.0-129.0
2-045 CF ₃ HHFF Cl Ph-2,4,5-F ₃ 127.0-129.0
2-046 CF ₃ HHFF Cl Ph-2,4,6-F ₃ 173.0-177.0
2-047 CF ₃ HHFF Cl Ph-3,4,5-F ₃ 121.0-123.0
2-048 CF ₃ HHFF Cl Ph-2,6-F ₂ -4-Cl 167.0-169.0
2-049 CF ₃ HHFF Cl 2-Naph 175.0-176.0
2-050 CF ₃ HHFF Cl (D-2-2b) -2-CH ₃ -5-Cl 157.0-160.0
2-051 FHH -CH ₂ CH ₂ -Cl Ph-4-Cl 137.0-140.0
2-052 Cl HH -CH ₂ CH ₂ -Cl Ph-4-Cl 194.0-195.0
2-053 CH ₃ HH -CH ₂ CH ₂ -Cl Ph-4-Cl 151.0-152.0
2-054 CF ₃ HH -CH ₂ CH ₂ -Cl Ph-4-Cl 149.0-151.0
2-055 Cl CH ₃ HFF Cl Ph-2-F 107.0-111.0
2-056 CF ₃ CH ₃ HFF Cl Ph-2-F 135.0-138.0
2-057 CF ₃ CH ₃ HFF Cl Ph-4-F 141.0-143.0
2-058 Cl CH ₃ HFF Cl Ph-4-CF ₃ * 1
2-059 CF ₃ CH ₃ HFF Cl Ph-4-CF ₃ 119.0-121.0
2-060 Cl CH ₃ HFF Cl Ph-2,4-F ₂ 115.0-117.0
2-061 CF ₃ CH ₃ HFF Cl Ph-2,4-F ₂ 138.0-139.0
2-062 Cl CH ₃ HFF Cl Ph-3,4-F ₂ 91.0-101.0
2-063 CF ₃ CH ₃ HFF Cl Ph-3,4-F ₂ 125.0-127.0
2-064 CF ₃ CH ₃ HFF Cl Ph-3,4-Cl ₂ 142.0-145.0
2-065 CF ₃ CH ₃ HFF Cl Ph-2-F-4-CH ₃ 141.0-144.0
2-066 CF ₃ CH ₃ HFF Cl Ph-2-CH ₃ -4-Cl 124.0-126.0
2-067 CF ₃ CH ₃ HFF Cl Ph-2-F-4-CF ₃ 109.0-111.0
2-068 CF ₃ CH ₃ HFF Cl Ph-3-OCH ₃ -4-Cl 162.0-164.0
2-069 CF ₃ CH ₃ HFF Cl Ph-2,4,6-F ₃ 152.0-157.0
2-070 CF ₃ CH ₃ HFF Cl Ph-3,4,5-F ₃ 120.0-121.0
――――――――――――――――――――――――――――――――――――――――
Table 5

――――――――――――――――――――――――――――――――――――――――
No. X ¹ R ³ R ⁴ R ¹ R ² Y ¹ R ⁶ mp (℃)
――――――――――――――――――――――――――――――――――――――――
3-001 Cl HHFF Cl Ph-2-F 177.0-179.0
3-002 Cl HHFF Cl Ph-3-F * 1
3-003 Cl HHFF Cl Ph-4-F 143.0-146.0
3-004 CF ₃ HHFF Cl Ph-3-Cl 175.0-177.5
3-005 Cl HHFF Cl Ph-2-CF ₃ 161.0-163.0
3-006 Cl HHFF Cl Ph-3-CF ₃ 111.0-113.0
3-007 CHF ₂ HHFF Cl Ph-3-OCH ₃ 142.0-143.0
3-008 Cl HHFF Cl Ph-4-CN 179.0-181.0
3-009 Cl HHFF Cl D-2-2a 142.0-143.0
3-010 Cl HH CH ₃ F Cl Ph-4-F 149.0-151.0
3-011 Cl CH ₃ HFF Cl Ph-4-F 155.0-159.0
3-012 Cl HHHH Cl Ph-4-F 107.0-109.0
3-013 Cl HHFH Cl Ph-4-F 135.0-138.0
3-014 CHF ₂ HHFF Cl Ph-4-F 139.0-141.0
3-015 CF ₃ HHFF Cl Ph-4-F 170.0-172.0
3-016 SCH ₃ HHFF Cl Ph-4-F 144.0-146.0
3-017 SO ₂ CH ₃ HHFF Cl Ph-4-F 171.0-174.0
3-018 SO ₂ CHF ₂ HHFF Cl Ph-4-F * 1
3-019 Cl HHFF Cl Ph-2-Cl 162.5-164.0
3-020 Cl HHFF Cl Ph-3-Cl 129.0-131.0
3-021 Cl HHFF Cl Ph-4-Cl 155.0-158.0
3-022 Cl HHFF Cl Ph-4-Br 162.5-164.5
3-023 Cl HHFF Cl Ph-2-CH ₃ 102.0-105.0
3-024 Cl HHFF Cl Ph-3-CH ₃ 116.0-119.0
3-025 Cl HHFF Cl Ph-4-CH ₃ 114.0-116.0
3-026 Cl HHFF Cl Ph-4-Bu-t * 1
3-027 Cl HHFF Cl Ph-2-OCH ₃ 113.0-118.0
3-028 Cl HHFF Cl Ph-3-OCH ₃ 131.0-134.0
3-029 Cl HHFF Cl Ph-4-OCH ₃ 144.0-147.0
3-030 Cl HHFF Cl Ph-4-OCHF ₂ 133.0-137.0
3-031 Cl HHFF Cl Ph-4-OCF ₃ 126.0-129.0
3-032 Cl HHFF Cl Ph-4-SCH ₃ 161.0-166.0
3-033 Cl HHFF Cl Ph-4-S (O) CH ₃ 152.0-154.0
3-034 Cl HHFF Cl Ph-4-SO ₂ CH ₃ 173.0-180.0
3-035 Cl HHFF Cl Ph-4-SCF ₃ 147.0-149.0
3-036 Cl HHFF Cl Ph-2,4-F ₂ 148.0-150.0
3-037 Cl HHFF Cl Ph-3,4-F ₂ 129.5-131.5
3-038 Cl HHFF Cl Ph-3,5-F ₂ 152.5-153.5
3-039 Cl HHFF Cl Ph-3-Cl-4-F 143.0-144.0
3-040 Cl HHFF Cl Ph-2-F-4-Cl 139.0-143.0
3-041 Cl HHFF Cl Ph-3-F-4-Cl 134.0-138.0
3-042 Cl HHFF Cl Ph-3,4-Cl ₂ 163.0-166.0
3-043 Cl HHFF Cl Ph-3-F-4-OCF ₃ 125.0-127.0
3-044 Cl HHFF Cl D-1-2a 139.5-141.5
3-045 Cl HHFF Cl D-2-1a 139.0-141.0
3-046 SO ₂ CH ₃ HHFF Cl D-2-1a 179.0-181.0
3-047 Cl HHFF Cl (D-8-2b) -2-CH ₃ 149.0-150.5
3-048 Cl HHFF Cl (D-23-2b) -6-Cl 157.0-159.0
3-049 Cl HHFF Cl (D-23-3b) -2-F 133.0-135.0
3-050 Cl HH CH ₃ H Cl Ph-4-F 129.0-130.0
3-051 Cl HH CH ₃ CH ₃ Cl Ph-4-F * 1
3-052 Cl HH -CH ₂ CH ₂ -Cl Ph-4-F 107.0-109.0
3-053 Cl CH ₃ HHH Cl Ph-4-F 111.0-112.0
3-054 Cl CH ₃ HFF Cl Ph-4-Cl 149.0-152.0
3-055 CF ₃ CH ₃ HFF Cl Ph-4-Cl 183.0-184.0
3-056 SO ₂ CH ₃ CH ₃ HFF Cl Ph-4-Cl 173.0-177.0
3-057 SO ₂ CHF ₂ CH ₃ HFF Cl Ph-4-Cl 186.0-189.0
3-058 Cl CH ₃ HFF Cl Ph-4-CF ₃ 156.0-160.0
3-059 CHF ₂ CH ₃ HFF Cl Ph-4-CF ₃ * 1
3-060 Cl CH ₃ HFF Cl Ph-4-OCH ₃ 171.0-173.0
3-061 Cl CH ₃ HFF Cl Ph-4-CN 196.0-197.0
3-062 Cl CH ₃ H OCH ₃ H Cl Ph-4-F * 1
3-063 Cl HHHH Cl Ph-2-F 129.0-131.0
3-064 CF ₃ HHHH Cl Ph-2-F 136.0-137.0
3-065 Cl HHHH Cl Ph-4-Cl 140.0-141.0
3-066 Cl HHHH Cl Ph-4-CF ₃ 140.0-142.0
3-067 Cl HHHH Cl Ph-2-F-4-Cl 136.0-139.0
3-068 CF ₃ HHFH Cl Ph-4-Cl 148.0-149.0
3-069 Cl HHFH Cl Ph-2-F-4-Cl 206.0-207.0
3-070 CF ₃ HHFF Cl Ph-3,4-Cl ₂ 153.0-156.0
3-071 Cl HHFF Cl Ph-2-F-4-CH ₃ 170.0-172.0
3-072 CF ₃ HHFF Cl Ph-2-F-4-CH ₃ 194.0-196.0
3-073 Cl HHFF Cl Ph-3-CF ₃ -4-Cl 151.0-154.0
3-074 CF ₃ HHFF Cl Ph-3-CF ₃ -4-Cl 177.0-179.0
3-075 SO ₂ CH ₃ HHFF Cl Ph-3-CF ₃ -4-Cl 72.0-77.0
3-076 Cl HHFF Cl (D-1-2b) -2-CH ₃ * 1
3-077 CF ₃ HHFF Cl (D-1-2b) -2-CH ₃ 144.0-146.0
3-078 Cl HHFF Cl (D-2-2b) -5-CH ₃ 139.0-140.0
3-079 Cl HHFF Cl (D-23-2b) -6-CF ₃ 178.0-181.0
3-080 Cl HHFF Cl (D-23-3b) -3-F 119.0-121.0
3-081 Cl HHFF Cl D-25-1a 210.0-211.0
3-082 CF ₃ HHFF Cl D-25-1a 206.0-207.0
3-083 Cl HHFF Cl D-25-3a 171.0-173.0
3-084 Cl HH CH ₃ H Cl Ph-2-F 109.0-112.0
3-085 CF ₃ HH CH ₃ H Cl Ph-2-F 127.0-129.0
3-086 SO ₂ CH ₃ CH ₃ HFF Cl Ph-4-F 188.0-190.0
3-087 CH ₃ CH ₃ HFF Cl Ph-4-Cl 159.0-161.0
3-088 OCH ₃ CH ₃ HFF Cl Ph-4-Cl 105.0-107.0
3-089 Cl CH ₃ HFF Cl Ph-2-F-4-Cl 141.0-147.0
3-090 CF ₃ CH ₃ HFF Cl Ph-2-F-4-Cl 178.0-179.0
3-091 Cl CH ₃ HFF Cl Ph-3-F-4-Cl 153.0-155.0
3-092 CF ₃ CH ₃ HFF Cl Ph-3-F-4-Cl 162.0-166.0
3-093 Cl CH ₃ HFF Cl (D-23-2b) -6-F 170.0-172.0
3-094 CF ₃ CH ₃ HFF Cl (D-23-2b) -6-F 122.0-124.0
3-095 Cl HHHH Cl Ph-3-F 121.0-123.0
3-096 CF ₃ HHFF Cl Ph-4-Cl 169.0-171.0
3-097 CF ₃ HHFF Cl Ph-4-Br 210.0-212.0
3-098 Cl HHFF Cl Ph-4-CF ₃ 162.5-164.0
3-099 CF ₃ HHFF Cl Ph-4-CF ₃ 172.0-174.0
3-100 CF ₃ HHFF Cl Ph-4-OCHF ₂ 152.0-154.0
3-101 Cl HHFF Cl Ph-4-S (O) CF ₃ 141.0-144.0
3-102 CF ₃ HHFF Cl Ph-4-S (O) CF ₃ 150.0-152.0
3-103 CF ₃ HHFF Cl Ph-4-SO ₂ CF ₃ 93.0-96.0
3-104 CF ₃ HHFF Cl Ph-2,4-F ₂ 153.0-155.0
3-105 CF ₃ HHFF Cl Ph-2-F-4-Cl 200.0-202.0
3-106 CF ₃ HHFF Cl Ph-3-F-4-Cl 181.0-183.0
3-107 CF ₃ HHFF Cl Ph-2,4-Cl ₂ 182.0-183.0
3-108 Cl HHFF Cl Ph-2-CH ₃ -4-F 128.0-129.0
3-109 CF ₃ HHFF Cl Ph-2-CH ₃ -4-F 129.0-130.0
3-110 Cl HHFF Cl Ph-2-CH ₃ -4-Cl 143.0-146.0
3-111 CF ₃ HHFF Cl Ph-2-CH ₃ -4-Cl 152.5-154.5
3-112 Cl HHFF Cl Ph-2-CF ₃ -4-F 158.0-161.0
3-113 CF ₃ HHFF Cl Ph-2-CF ₃ -4-F 183.0-185.0
3-114 Cl HHFF Cl Ph-2-F-3-CF ₃ 163.0-164.0
3-115 CF ₃ HHFF Cl Ph-2-F-3-CF ₃ 158.0-160.0
3-116 Cl HHFF Cl Ph-3-CF ₃ -4-F 173.0-174.0
3-117 CF ₃ HHFF Cl Ph-3-CF ₃ -4-F 154.0-155.0
3-118 Cl HHFF Cl Ph-2-F-4-CF ₃ 156.0-157.0
3-119 CF ₃ HHFF Cl Ph-2-F-4-CF ₃ 191.0-193.0
3-120 Cl HHFF Cl Ph-3-OCH ₃ -4-F 181.0-183.0
3-121 CF ₃ HHFF Cl Ph-3-OCH ₃ -4-F 167.0-169.0
3-122 Cl HHFF Cl Ph-2-F-4-OCH ₃ 175.0-177.0
3-123 CF ₃ HHFF Cl Ph-2-F-4-OCH ₃ 174.0-176.0
3-124 Cl HHFF Cl Ph-3-OCH ₃ -4-Cl 171.0-172.0
3-125 CF ₃ HHFF Cl Ph-3-OCH ₃ -4-Cl 177.0-180.0
3-126 Cl HHFF Cl Ph-2-F-4-OCF ₃ 147.0-149.0
3-127 CF ₃ HHFF Cl Ph-2-F-4-OCF ₃ 166.0-167.0
3-128 CF ₃ HHFF Cl Ph-3-F-4-OCF ₃ 155.0-157.0
3-129 Cl HHFF Cl T-15 162.0-166.0
3-130 CF ₃ HHFF Cl T-15 159.0-161.0
3-131 CF ₃ HHFF Cl Ph-2,4,5-F ₃ 172.0-174.0
3-132 Cl HHFF Cl Ph-2,4,6-F ₃ 168.0-171.0
3-133 CF ₃ HHFF Cl Ph-2,4,6-F ₃ 162.0-167.0
3-134 Cl HHFF Cl Ph-3,4,5-F ₃ 145.0-147.0
3-135 CF ₃ HHFF Cl Ph-3,4,5-F ₃ 153.0-157.0
3-136 CF ₃ HHFF Cl Ph-2,6-F ₂ -4-Cl 190.0-194.0
3-137 CF ₃ HHFF Cl 2-Naph 194.0-196.0
3-138 CF ₃ HHFF Cl (D-2-2b) -2-CH ₃ -5-Cl 117.0-120.0
3-139 Cl CH ₃ HFF Cl Ph-2-F 142.0-146.0
3-140 CF ₃ CH ₃ HFF Cl Ph-2-F 154.0-157.0
3-141 CF ₃ CH ₃ HFF Cl Ph-4-F 161.0-163.0
3-142 CF ₃ CH ₃ HFF Cl Ph-4-CF ₃ 150.0-154.0
3-143 SO ₂ CH ₃ CH ₃ HFF Cl Ph-4-CF ₃ 169.0-173.0
3-144 Cl CH ₃ HFF Cl Ph-2,4-F ₂ 160.0-162.0
3-145 CF ₃ CH ₃ HFF Cl Ph-2,4-F ₂ 174.0-178.0
3-146 Cl CH ₃ HFF Cl Ph-3,4-F ₂ 128.0-130.0
3-147 CF ₃ CH ₃ HFF Cl Ph-3,4-F ₂ 139.0-141.0
3-148 CH ₃ CH ₃ HFF Cl Ph-2-F-4-Cl 161.0-163.0
3-149 Cl CH ₃ HFF Cl Ph-3,4-Cl ₂ 167.0-169.0
3-150 CF ₃ CH ₃ HFF Cl Ph-3,4-Cl ₂ 120.0-122.0
3-151 CF ₃ CH ₃ HFF Cl Ph-2-F-4-CH ₃ 170.0-172.0
3-152 CF ₃ CH ₃ HFF Cl Ph-2-CH ₃ -4-Cl 181.0-182.0
3-153 CF ₃ CH ₃ HFF Cl Ph-2-F-4-CF ₃ 158.0-161.0
3-154 CF ₃ CH ₃ HFF Cl Ph-3-OCH ₃ -4-Cl 182.0-185.0
3-155 CF ₃ CH ₃ HFF Cl Ph-2,4,6-F ₃ 186.0-188.0
3-156 CF ₃ CH ₃ HFF Cl Ph-3,4,5-F ₃ 142.0-146.0
――――――――――――――――――――――――――――――――――――――――
Table 6

――――――――――――――――――――――――――――――――――――――――
No. X ¹ R ³ R ⁴ R ¹ R ² Y ¹ R ⁶ mp (℃)
――――――――――――――――――――――――――――――――――――――――
4-001 CF ₃ HHFF Cl Ph-4-F 172.0-174.0
4-002 Cl HHFF Cl Ph-4-F 114.0-117.0
4-003 Cl HHFF Cl Ph-3-F-4-Cl 113.0-116.0
4-004 Cl CH ₃ HFF Cl Ph-4-Cl 102.0-107.0
4-005 Cl HHFF Cl (D-2-2b) -5-CH ₃ 129.0-131.0
4-006 Cl CH ₃ HFF Cl Ph-2-F 149.0-152.0
4-007 Cl CH ₃ HFF Cl Ph-4-CF ₃ 147.0-149.0
4-008 Cl CH ₃ HFF Cl Ph-2,4-F ₂ 133.0-136.0
4-009 Cl CH ₃ HFF Cl Ph-2-F-4-Cl 124.0-127.0
――――――――――――――――――――――――――――――――――――――――
Table 7

――――――――――――――――――――――――――――――――――――――――
No. X ¹ R ³ R ⁴ R ¹ R ² Y ¹ R ⁶ mp (℃)
――――――――――――――――――――――――――――――――――――――――
5-001 Br HHFF Cl Ph-4-OCF ₃ * 1
――――――――――――――――――――――――――――――――――――――――
Table 8

――――――――――――――――――――――――――――――――――――――――
No. X ¹ X ³ R ³ R ⁴ R ¹ R ² Y ¹ R ⁶ mp (℃)
――――――――――――――――――――――――――――――――――――――――
6-001 CH ₃ HHHFF Cl Ph-4-F 104.0-105.0
6-002 CF ₃ CH ₃ HHFF Cl Ph-4-F 111.0-112.0
6-003 CF ₃ CH ₃ HHFF Cl Ph-4-OCF ₃ 116.0-118.0
――――――――――――――――――――――――――――――――――――――――
Table 9

――――――――――――――――――――――――――――――――――――――――
No. X ¹ R ³ R ⁴ R ¹ R ² Y ¹ R ⁶ mp (℃)
――――――――――――――――――――――――――――――――――――――――
7-001 CH ₃ HHFF Cl Ph-4-F 114.0-115.0
7-002 CF ₃ HHFF Cl Ph-4-F 109.0-111.0
7-003 CF ₃ HHFF Cl Ph-3-OCH ₃ 103.0-105.0
7-004 CH ₃ HHFF Cl Ph-3,4-F ₂ 127.5-129.5
7-005 CF ₃ HH CH ₃ F Cl Ph-4-F 101.0-103.0
7-006 CF ₃ CH ₃ HFF Cl c-Pr 98.0-101.0
7-007 CF ₃ HHHH Cl Ph-4-F * 1
7-008 Cl HHFF Cl Ph-4-F 153.0-156.0
7-009 Cl HHFF Cl Ph-4-Cl 141.5-143.5
7-010 CF ₃ HHFF Cl Ph-3,4-Cl ₂ 92.0-95.0
7-011 CF ₃ HHFF Cl (D-23-3b) -2-F 126.0-128.0
7-012 CF ₃ CH ₃ HFF Cl C (CH ₃ ) ₂ F * 1
7-013 CF ₃ CH ₃ HFF Cl Ph-4-Cl 127.0-131.0
7-014 CF ₃ HHFF Cl (D-23-2b) -6-CF ₃ 145.0-149.0
7-015 CF ₃ HHFF Cl (D-23-3b) -3-F 93.0-95.0
7-016 CF ₃ HHFF Cl D-25-3a 137.0-139.0
7-017 CF ₃ CH ₃ HFF Cl (D-23-2b) -6-F 132.0-137.0
7-018 CF3 HHFF Cl Ph-2-F-4-Cl 113.0-114.5
7-019 CF ₃ CH ₃ HFF Cl Ph-2,4-F ₂ 105.0-107.0
7-020 CF ₃ CH ₃ HFF Cl Ph-2-F-4-Cl 121.0-123.0
7-021 CF ₃ CH ₃ HFF Cl Ph-3,4-Cl ₂ 107.0-109.0
7-022 CF ₃ CH ₃ HFF Cl (D-23-2b) -6-Cl 141.0-143.0
――――――――――――――――――――――――――――――――――――――――
Table 10

――――――――――――――――――――――――――――――――――――――――
No. X ¹ R ³ R ⁴ R ¹ R ² Y ¹ R ⁶ mp (℃)
――――――――――――――――――――――――――――――――――――――――
8-001 IHHFF Cl Ph-4-F 126.0-128.0
8-002 IHHFF Cl Ph-3-Cl 120.5-122.0
8-003 I CH ₃ HFF Cl c-Pr 168.0-170.0
8-004 I CH ₃ HFF Cl Ph-4-Cl 121.0-123.0
8-005 I CH ₃ HFF Cl Ph-2-F-4-Cl * 1
――――――――――――――――――――――――――――――――――――――――
Table 11

――――――――――――――――――――――――――――――――――――――――
No. X ¹ R ³ R ⁴ R ¹ R ² Y ¹ R ⁶ mp (℃)
――――――――――――――――――――――――――――――――――――――――
9-001 CHF ₂ HHFF Cl Ph-4-F 137.0-139.0
9-002 CHF ₂ HHFF Cl Ph-3,5-F ₂ 119.0-122.0
9-003 CHF ₂ CH ₃ HFF Cl c-Pr * 1
9-004 CHF ₂ CH ₃ HHH Cl Ph-4-F * 1
9-005 CHF ₂ CH ₃ HHH Cl Ph-2-F * 1
9-006 CHF ₂ CH ₃ HHH Cl Ph-4-Cl 146.0-148.0
9-007 CHF ₂ HHFF Cl Ph-4-S (O) CF ₃ * 1
9-008 CHF ₂ HHFF Cl Ph-3-F-4-OCF ₃ 116.0-118.0
9-009 CHF ₂ CH ₃ HHH Cl Ph-2-F-4-Cl * 1
9-010 CHF ₂ CH ₃ HFF Cl Ph-2-F-4-CF ₃ * 1
9-011 CF ₃ CH ₃ HFF Cl Ph-2,4,6-F ₃ 149.0-152.0
――――――――――――――――――――――――――――――――――――――――
Table 12

――――――――――――――――――――――――――――――――――――――――
No. X ¹ X ³ R ³ R ⁴ R ¹ R ² Y ¹ R ⁶ mp (℃)
――――――――――――――――――――――――――――――――――――――――
10-001 CF ₃ CH ₃ HHFF Cl Ph-4-F * 1
――――――――――――――――――――――――――――――――――――――――
Table 13

――――――――――――――――――――――――――――――――――――――――
No. X ¹ X ³ R ³ R ⁴ R ¹ R ² Y ¹ R ⁶ mp (℃)
――――――――――――――――――――――――――――――――――――――――
11-001 CF ₃ H CH ₃ HFF Cl Ph-2-F-4-Cl * 1
――――――――――――――――――――――――――――――――――――――――
Table 14

――――――――――――――――――――――――――――――――――――――――
No. X ¹ R ³ R ⁴ R ¹ R ² Y ¹ R ⁶ mp (℃)
――――――――――――――――――――――――――――――――――――――――
12-001 CF ₃ HHFF Cl Ph-4-F 149.0-152.0
12-002 CF ₃ HHFF Cl Ph-4-CH ₃ 153.0-155.0
12-003 CF ₃ HHFF Cl Ph-2-F-4-CH ₃ 156.0-158.0
――――――――――――――――――――――――――――――――――――――――
Table 15

――――――――――――――――――――――――――――――――――――――――
No. X ¹ r R ³ R ⁴ R ¹ R ² Y ¹ R ⁶ mp (℃)
――――――――――――――――――――――――――――――――――――――――
13-001 CF ₃ 0 HHFF Cl Ph-4-F 151.0-153.0
13-002 CF ₃ 1 HHFF Cl Ph-4-F 174.0-178.0
13-003 CF ₃ 2 HHFF Cl Ph-4-F 168.0-170.0
――――――――――――――――――――――――――――――――――――――――
Table 16

――――――――――――――――――――――――――――――――――――――――
No. X ¹ R ³ R ⁴ R ¹ R ² Y ¹ R ⁶ mp (℃)
――――――――――――――――――――――――――――――――――――――――
14-001 FHHFF Cl Ph-2-F 160.0-161.0
14-002 FHHFF Cl Ph-3-F 138.0-140.0
14-003 FHHFF Cl Ph-4-F 174.0-177.0
14-004 FHHFF Cl Ph-2-CF ₃ 148.0-150.0
14-005 FHHFF Cl Ph-3-CF ₃ 141.0-143.0
14-006 FHHFF Cl Ph-4-CN 203.0-205.0
14-007 FHHFF Cl Ph-3,4-F ₂ 126.0-128.0
14-008 FHHFF Cl D-2-2a 157.0-159.0
14-009 F CH ₃ HFF Cl Ph-4-F 145.0-148.0
14-010 FHHHH Cl Ph-4-F 144.0-146.0
14-011 FHHFH Cl Ph-4-F 147.0-149.0
14-012 FHHFF Cl Ph-2-Cl 163.5-164.5
14-013 FHHFF Cl Ph-3-Cl 164.0-166.0
14-014 FHHFF Cl Ph-4-Cl 132.5-135.5
14-015 FHHFF Cl Ph-4-Br 158.5-159.5
14-016 FHHFF Cl Ph-2-CH ₃ 151.0-153.0
14-017 FHHFF Cl Ph-3-CH ₃ 174.0-177.0
14-018 FHHFF Cl Ph-4-CH ₃ 177.0-180.0
14-019 FHHFF Cl Ph-4-Bu-t * 1
14-020 FHHFF Cl Ph-2-OCH ₃ 155.0-158.0
14-021 FHHFF Cl Ph-3-OCH ₃ 134.0-139.0
14-022 FHHFF Cl Ph-4-OCH ₃ 156.0-159.0
14-023 FHHFF Cl Ph-4-OCHF ₂ 138.0-139.0
14-024 FHHFF Cl Ph-4-OCF ₃ 123.0-126.0
14-025 FHHFF Cl Ph-4-SCH ₃ 150.0-155.0
14-026 FHHFF Cl Ph-4-S (O) CH ₃ 184.0-187.0
14-027 FHHFF Cl Ph-4-SO ₂ CH ₃ 182.0-185.0
14-028 FHHFF Cl Ph-4-SCF ₃ 122.0-124.0
14-029 FHHFF Cl Ph-4-NO ₂ 197.0-199.0
14-030 FHHFF Cl Ph-2,4-F ₂ 157.0-160.0
14-031 Cl HHFF Cl Ph-2,4-F ₂ 187.5-190.0
14-032 FHHFF Cl Ph-3,5-F ₂ 148.0-151.0
14-033 FHHFF Cl Ph-3-Cl-4-F 158.0-159.0
14-034 FHHFF Cl Ph-2-F-4-Cl 119.0-121.0
14-035 FHHFF Cl Ph-3-F-4-Cl 133.0-135.0
14-036 FHHFF Cl Ph-3,4-Cl ₂ 173.0-174.0
14-037 FHHFF Cl Ph-3-F-4-OCF ₃ 120.0-121.5
14-038 CF ₃ HHFF Cl Ph-3-F-4-OCF ₃ 125.0-126.0
14-039 FHHFF Cl Ph-3,4,5-F ₃ 165.0-168.0
14-040 FHHFF Cl D-1-2a 146.0-149.0
14-041 FHHFF Cl D-2-1a 144.0-146.0
14-042 FHHFF Cl (D-8-2b) -2-CH ₃ 147.5-149.5
14-043 FHHFF Cl (D-23-2b) -6-Cl 170.0-174.0
14-044 FHHFF Cl (D-23-3b) -2-F 136.0-139.0
14-045 FHH CH ₃ H Cl Ph-4-F 162.0-164.0
14-046 FHH CH ₃ CH ₃ Cl Ph-4-F * 1
14-047 FHH -CH ₂ CH ₂ -Cl Ph-4-F 148.0-149.0
14-048 F CH ₃ HHH Cl Ph-4-F 167.0-169.0
14-049 F CH ₃ HFF Cl Ph-4-Cl 164.0-166.0
14-050 F CH ₃ HFF Cl Ph-4-CF ₃ 176.0-177.0
14-051 FHHFF Cl (D-23-2b) -6-F 155.0-157.0
14-052 FHHFF Cl (D-23-2b) -6-CF ₃ 155.0-159.0
14-053 FHHFF Cl (D-23-3b) -3-F 136.0-139.0
――――――――――――――――――――――――――――――――――――――――
Table 17

――――――――――――――――――――――――――――――――――――――――
No. X ¹ R ⁵ R ³ R ⁴ R ¹ R ² R ⁶ mp (℃)
――――――――――――――――――――――――――――――――――――――――
15-001 CF ₃ c-Pr CH ₃ HFF c-Pr * 1
――――――――――――――――――――――――――――――――――――――――
Table 18

――――――――――――――――――――――――――――――――――――――――
No. R ³ R ⁴ R ¹ R ² Y ¹ R ⁶ mp (℃)
――――――――――――――――――――――――――――――――――――――――
16-001 HHFF Cl Ph-2-F 49.0-51.0
16-002 HHFF Cl Ph-3-F * 1
16-003 HHFF Cl Ph-4-F * 1
16-004 HHFF Cl Ph-4-CF ₃ 72.0-74.0
16-005 HHFF Cl Ph-3,4-F ₂ 110.0-113.0
16-006 HHFF Cl D-2-2a 68.0-70.0
16-007 HHFF Cl D-23-2a 103.0-105.0
16-008 HHFF Cl D-23-3a 113.0-115.0
16-009 HH CH ₃ F Cl Ph-4-F * 1
16-010 CH ₃ HFF Cl c-Pr * 1
16-011 CH ₃ HFF Cl Ph-4-Cl * 1
16-012 HHHH Cl Ph-4-F 116.0-119.0
16-013 HHFH Cl Ph-4-F * 1
16-014 HHFF Cl Ph-2-Cl 66.5-68.0
16-015 HHFF Cl Ph-3-Cl * 1
16-016 HHFF Cl Ph-4-Cl 85.0-88.0
16-017 HHFF Cl Ph-4-Br 96.0-98.0
16-018 HHFF Cl Ph-2-CH ₃ * 1
16-019 HHFF Cl Ph-3-CH ₃ 51.0-53.0
16-020 HHFF Cl Ph-4-CH ₃ 63.0-65.0
16-021 HHFF Cl Ph-4-Bu-t 73.0-76.0
16-022 HHFF Cl Ph-2-CF ₃ * 1
16-023 HHFF Cl Ph-3-CF ₃ * 1
16-024 HHFF Cl Ph-2-OCH ₃ 84.0-86.0
16-025 HHFF Cl Ph-3-OCH ₃ 83.0-87.0
16-026 HHFF Cl Ph-4-OCH ₃ * 1
16-027 HHFF Cl Ph-4-OCHF ₂ * 1
16-028 HHFF Cl Ph-4-OCF ₃ * 1
16-029 HHFF Cl Ph-4-SCH ₃ 104.0-108.0
16-030 HHFF Cl Ph-4-S (O) CH ₃ 109.0-112.0
16-031 HHFF Cl Ph-4-SO ₂ CH ₃ 136.0-138.0
16-032 HHFF Cl Ph-4-SCF ₃ 62.0-65.0
16-033 HHFF Cl Ph-4-NO ₂ 90.0-94.0
16-034 HHFF Cl Ph-4-CN * 1
16-035 HHFF Cl Ph-2,4-F ₂ 53.0-56.0
16-036 HHFF Cl Ph-3,5-F ₂ 84.0-87.0
16-037 HHFF Cl Ph-3-Cl-4-F 73.0-76.0
16-038 HHFF Cl Ph-2-F-4-Cl 78.0-81.0
16-039 HHFF Cl Ph-3-F-4-Cl 70.0-73.0
16-040 HHFF Cl Ph-3,4-Cl ₂ 73.0-76.0
16-041 HHFF Cl Ph-3-F-4-OCF ₃ * 1
16-042 HHFF Cl Ph-3,4,5-F ₃ 109.0-111.0
16-043 HHFF Cl D-1-2a * 1
16-044 HHFF Cl D-2-1a * 1
16-045 HHFF Cl (D-8-2b) -2-CH ₃ 82.0-84.0
16-046 HHFF Cl (D-23-2b) -6-F 109.0-111.0
16-047 HHFF Cl (D-23-2b) -6-Cl 142.0-144.0
16-048 HHFF Cl (D-23-3b) -2-F 98.0-100.0
16-049 HH CH ₃ H Cl Ph-4-F * 1
16-050 HH CH ₃ CH ₃ Cl Ph-4-F 60.0-62.0
16-051 HH -CH ₂ CH ₂ -Cl Ph-4-F * 1
16-052 CH ₃ HHH Cl Ph-4-F * 1
16-053 CH ₃ HFF Cl Ph-4-OCH ₃ * 1
16-054 CH ₃ HFF Cl Ph-4-CN * 1
16-055 CH ₃ H OCH ₃ H Cl Ph-4-F * 1
16-056 HHHH Cl Ph-2-F 85.0-88.0
16-057 HHHH Cl Ph-4-Cl 60.0-63.0
16-058 HHHH Cl Ph-4-CF ₃ 103.0-106.0
16-059 HHHH Cl Ph-2-F-4-Cl 73.0-77.0
16-060 HHFH Cl Ph-4-Cl * 1
16-061 HHFH Cl Ph-2-F-4-Cl * 1
16-062 HHFF Cl Ph-2-F-4-CH ₃ 89.0-90.0
16-063 HHFF Cl Ph-3-CF ₃ -4-Cl 69.0-71.0
16-064 HHFF Cl (D-1-2b) -2-CH ₃ * 1
16-065 HHFF Cl (D-2-2b) -5-CH ₃ * 1
16-066 HHFF Cl (D-6-1a) -1-CH ₃ * 1
16-067 HHFF Cl D-23-1a * 1
16-068 HHFF Cl (D-23-2b) -6-CF ₃ 137.0-139.0
16-069 HHFF Cl (D-23-3b) -3-F 125.0-127.0
16-070 HHFF Cl D-25-1a 102.0-104.0
16-071 HHFF Cl D-25-3a 149.0-151.0
16-072 HH CH ₃ H Cl Ph-2-F * 1
16-073 CH ₃ HFF Cl Ph-2-F * 1
16-074 CH ₃ HFF Cl Ph-4-CF ₃ * 1
16-075 CH ₃ HFF Cl Ph-2-F-4-Cl 69.0-71.0
16-076 CH ₃ HFF Cl Ph-3-F-4-Cl 72.0-74.0
16-077 CH ₃ HFF Cl (D-23-2b) -6-F 84.0-86.0
16-078 HHHH Cl Ph-3-F * 1
16-079 HHFF Cl Ph-4-S (O) CF ₃ 81.0-83.0
16-080 HHFF Cl Ph-4-SO ₂ CF ₃ 124.0-125.0
16-081 HHFF Cl Ph-2,4-Cl ₂ 100.0-101.0
16-082 HHFF Cl Ph-2-CH ₃ -4-F 73.0-75.0
16-083 HHFF Cl Ph-2-CH ₃ -4-Cl 96.5-97.5
16-084 HHFF Cl Ph-2-CF ₃ -4-F 74.0-76.0
16-085 HHFF Cl Ph-2-F-3-CF ₃ 95.0-96.0
16-086 HHFF Cl Ph-3-CF ₃ -4-F 75.0-76.0
16-087 HHFF Cl Ph-2-F-4-CF ₃ 70.0-71.0
16-088 HHFF Cl Ph-3-OCH ₃ -4-F 89.0-90.0
16-089 HHFF Cl Ph-3-OCH ₃ -4-Cl 95.5-97.5
16-090 HHFF Cl Ph-2-F-4-OCH ₃ 89.5-91.5
16-091 HHFF Cl Ph-2-F-4-OCF ₃ 40.0-41.0
16-092 HHFF Cl T-15 90.0-93.0
16-093 HHFF Cl Ph-2,4,5-F ₃ 124.0-126.0
16-094 HHFF Cl Ph-2,4,6-F ₃ 105.0-107.0
16-095 HHFF Cl Ph-2,6-F ₂ -4-Cl 100.0-104.0
16-096 HHFF Cl Ph-3,5-F ₂ -4-Cl 120.0-122.0
16-097 HHFF Cl 2-Naph 84.0-85.0
16-098 HHFF Cl (D-2-2b) -2-CH ₃ -5-Cl 123.0-126.0
16-099 HHFF Cl (D-23-1b) -3,5-Cl ₂ 108.0-110.0
16-100 HH -CH ₂ CH ₂ -Cl Ph-4-Cl * 1
16-101 CH ₃ HHH Cl Ph-2-F-4-Cl * 1
16-102 CH ₃ HFF Cl Ph-2,4-F ₂ * 1
16-103 CH ₃ HFF Cl Ph-3,4-F ₂ 46.0-47.0
16-104 CH ₃ HFF Cl Ph-3,4-Cl ₂ 65.0-67.0
16-105 CH ₃ HFF Cl Ph-2-F-4-CH ₃ 57.0-60.0
16-106 CH ₃ HFF Cl Ph-2-CH ₃ -4-Cl * 1
16-107 CH ₃ HFF Cl Ph-2-F-4-CF ₃ * 1
16-108 CH ₃ HFF Cl Ph-3-OCH ₃ -4-Cl * 1
16-109 CH ₃ HFF Cl Ph-2,4,6-F ₃ 64.0-68.0
16-110 CH ₃ HFF Cl Ph-3,4,5-F ₃ 81.0-83.0
16-111 CH ₃ HFF Cl Ph-2,6-F ₂ -4-Cl * 1
16-112 CH ₃ HFF Cl (D-23-2b) -6-Cl 127.0-129.0
――――――――――――――――――――――――――――――――――――――――
Table 19

――――――――――――――――――――――――――――――――――――――――
No. R ³ R ⁴ R ¹ R ² Y ¹ R ⁶ mp (℃)
――――――――――――――――――――――――――――――――――――――――
17-001 HHFF Cl Ph-2-F 123.0-124.0
17-002 HHFF Cl Ph-3-F 99.0-102.0
17-003 HHFF Cl Ph-4-F 107.0-108.0
17-004 HHFF Cl Ph-3-Cl 123.0-126.0
17-005 HHFF Cl Ph-4-Cl 116.0-118.0
17-006 HHFF Cl Ph-2-CF ₃ 118.0-119.0
17-007 HHFF Cl Ph-3-CF ₃ 101.0-103.0
17-008 HHFF Cl Ph-4-CF ₃ 111.0-113.0
17-009 HHFF Cl Ph-3-OCH ₃ 60.0-62.0
17-010 HHFF Cl Ph-4-OCH ₃ 125.5-128.0
17-011 HHFF Cl Ph-4-CN 134.0-136.0
17-012 HHFF Cl Ph-2,4-F ₂ 108.0-109.5
17-013 HHFF Cl Ph-3,4-F ₂ 94.0-96.5
17-014 HHFF Cl Ph-3,5-F ₂ 92.5-94.0
17-015 HHFF Cl Ph-3-F-4-OCF ₃ 95.0-97.0
17-016 HHFF Cl D-2-2a 109.0-111.0
17-017 HHFF Cl D-23-2a 156.0-158.0
17-018 HHFF Cl D-23-3a 99.0-101.0
17-019 CH ₃ HFF Cl c-Pr * 1
17-020 CH ₃ HFF Cl Ph-4-Cl * 1
17-021 CH ₃ HFF Cl Ph-4-OCH ₃ * 1
17-022 CH ₃ HFF Cl Ph-4-CN * 1
17-023 HHHH Cl Ph-4-F 109.0-111.0
17-024 HHFF Cl Ph-2-Cl 133.0-134.0
17-025 HHFF Cl Ph-4-Br 117.0-120.0
17-026 HHFF Cl Ph-2-CH ₃ 95.0-97.0
17-027 HHFF Cl Ph-3-CH ₃ 111.0-112.0
17-028 HHFF Cl Ph-4-CH ₃ 108.0-110.0
17-029 HHFF Cl Ph-4-Bu-t * 1
17-030 HHFF Cl Ph-2-OCH ₃ 119.0-120.0
17-031 HHFF Cl Ph-4-OCHF ₂ 121.0-123.0
17-032 HHFF Cl Ph-4-OCF ₃ 116.0-118.0
17-033 HHFF Cl Ph-4-SCH ₃ 101.0-103.0
17-034 HHFF Cl Ph-4-S (O) CH ₃ 117.0-119.0
17-035 HHFF Cl Ph-4-SO ₂ CH ₃ * 1
17-036 HHFF Cl Ph-4-SCF ₃ 104.0-106.0
17-037 HHFF Cl Ph-4-NO ₂ 158.0-159.0
17-038 HHFF Cl Ph-3-Cl-4-F 125.0-128.0
17-039 HHFF Cl Ph-2-F-4-Cl 104.0-107.0
17-040 HHFF Cl Ph-3-F-4-Cl 111.0-114.0
17-041 HHFF Cl Ph-3,4-Cl ₂ 118.0-121.0
17-042 HHFF Cl Ph-3,4,5-F ₃ 108.0-110.0
17-043 HHFF Cl D-1-2a * 1
17-044 HHFF Cl D-2-1a 100.0-104.0
17-045 HHFF Cl (D-8-2b) -2-CH ₃ * 1
17-046 HHFF Cl (D-23-2b) -6-F * 1
17-047 HHFF Cl (D-23-2b) -6-Cl 114.0-117.0
17-048 HHFF Cl (D-23-3b) -2-F 110.0-113.0
17-049 HHFF Cl (D-23-3b) -3-F 112.0-114.0
17-050 HH CH ₃ H Cl Ph-4-F * 1
17-051 HH CH ₃ CH ₃ Cl Ph-4-F 70.0-73.0
17-052 HH -CH ₂ CH ₂ -Cl Ph-4-F 103.0-104.0
17-053 CH ₃ HHH Cl Ph-4-F 117.0-119.0
17-054 CH ₃ HFF Cl Ph-4-CF ₃ 99.0-101.0
17-055 CH ₃ H OCH ₃ H Cl Ph-4-F * 1
17-056 HHHH Cl Ph-2-F 129.0-129.5
17-057 HHHH Cl Ph-4-Cl 134.0-138.0
17-058 HHHH Cl Ph-4-CF ₃ 132.0-134.0
17-059 HHHH Cl Ph-2-F-4-Cl 123.0-125.0
17-060 HHFF Cl Ph-2-CH ₃ -4-F 98.0-99.0
17-061 HHFF Cl Ph-2-F-4-CH ₃ 119.0-121.0
17-062 HHFF Cl Ph-2-CH ₃ -4-Cl 114.0-116.0
17-063 HHFF Cl Ph-3-CF ₃ -4-Cl 143.0-145.0
17-064 HHFF Cl (D-1-2b) -2-CH ₃ * 1
17-065 HHFF Cl (D-2-2b) -5-CH ₃ * 1
17-066 HHFF Cl (D-6-1a) -1-CH ₃ * 1
17-067 HHFF Cl D-23-1a * 1
17-068 HHFF Cl (D-23-2b) -6-CF ₃ 113.0-115.0
17-069 HHFF Cl D-25-1a 119.0-121.0
17-070 HHFF Cl D-25-3a 153.0-155.0
17-071 HH CH ₃ H Cl Ph-2-F * 1
17-072 CH ₃ HFF Cl Si (CH ₃ ) ₃ 88.0-90.0
17-073 CH ₃ HFF Cl Ph-2-F 108.0-110.0
17-074 CH ₃ HFF Cl Ph-2-F-4-Cl 127.0-129.0
17-075 CH ₃ HFF Cl Ph-3-F-4-Cl 117.0-119.0
17-076 CH ₃ HFF Cl (D-23-2b) -6-F 123.0-124.0
17-077 HHHH Cl Ph-3-F * 1
17-078 HHFF Cl Ph-4-S (O) CF ₃ 122.0-124.0
17-079 HHFF Cl Ph-4-SO ₂ CF ₃ 122.0-125.0
17-080 HHFF Cl Ph-3,4-Cl ₂ 130.0-131.0
17-081 HHFF Cl Ph-2-CF ₃ -4-F 102.0-104.0
17-082 HHFF Cl Ph-2-F-3-CF ₃ 116.0-118.0
17-083 HHFF Cl Ph-3-CF ₃ -4-F 119.0-120.0
17-084 HHFF Cl Ph-2-F-4-CF ₃ 119.0-120.0
17-085 HHFF Cl Ph-3-OCH ₃ -4-F 121.5-122.5
17-086 HHFF Cl Ph-3-OCH ₃ -4-Cl 119.0-121.0
17-087 HHFF Cl Ph-2-F-4-OCH ₃ 114.5-115.5
17-088 HHFF Cl Ph-2-F-4-OCF ₃ 115.0-117.0
17-089 HHFF Cl T-15 94.0-97.0
17-090 HHFF Cl Ph-2,4,5-F ₃ 92.0-93.0
17-091 HHFF Cl Ph-2,4,6-F ₃ 130.0-132.0
17-092 HHFF Cl Ph-2,6-F ₂ -4-Cl 123.0-125.0
17-093 HHFF Cl Ph-3,5-F ₂ -4-Cl 148.0-151.0
17-094 HHFF Cl 2-Naph 96.0-98.0
17-095 HHFF Cl (D-2-2b) -2-CH ₃ -5-Cl * 1
17-096 HHFF Cl (D-23-1b) -3,5-Cl ₂ 108.0-110.0
17-097 HH -CH ₂ CH ₂ -Cl Ph-4-Cl 142.0-143.0
17-098 CH ₃ HHH Cl Ph-2-F-4-Cl * 1
17-099 CH ₃ HFF Cl Ph-2,4-F ₂ 93.0-96.0
17-100 CH ₃ HFF Cl Ph-3,4-F ₂ 122.0-124.0
17-101 CH ₃ HFF Cl Ph-3,4-Cl ₂ 104.0-107.0
17-102 CH ₃ HFF Cl Ph-2-F-4-CH ₃ 129.0-131.0
17-103 CH ₃ HFF Cl Ph-2-CH ₃ -4-Cl 109.0-111.0
17-104 CH ₃ HFF Cl Ph-2-F-4-CF ₃ 95.0-98.0
17-105 CH ₃ HFF Cl Ph-3-OCH ₃ -4-Cl 119.0-120.0
17-106 CH ₃ HFF Cl Ph-2,4,6-F ₃ 123.0-125.0
17-107 CH ₃ HFF Cl Ph-3,4,5-F ₃ 132.0-134.0
17-108 CH ₃ HFF Cl Ph-2,6-F ₂ -4-Cl 118.0-121.0
17-109 CH ₃ HFF Cl (D-23-2b) -6-Cl 138.0-139.0
――――――――――――――――――――――――――――――――――――――――
Table 20

――――――――――――――――――――――――――――――――――――――――
No. R ³ R ⁴ R ¹ R ² Y ¹ R ⁶ mp (℃)
――――――――――――――――――――――――――――――――――――――――
18-001 HH CH ₃ F Cl Ph-4-F 153.0-155.0
18-002 HHFH Cl Ph-4-F 184.0-186.0
18-003 HHFH Cl Ph-2-F 181.0-182.0
18-004 HHFH Cl Ph-4-Cl 182.0-184.0
18-005 HHFH Cl Ph-4-CF ₃ 171.0-173.0
18-006 HHFH Cl Ph-2-F-4-Cl 153.0-157.0
――――――――――――――――――――――――――――――――――――――――
Of the compounds shown in Tables 3 to 20, Table ¹ shows ¹ H NMR data of compounds having no melting point in the table.
Table 21 ――――――――――――――――――――――――――――――――――――――――
No. ¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz)
――――――――――――――――――――――――――――――――――――――――
1-012 δ8.65-8.7 (m, 2H), 8.59 (d, J = 1.7Hz, 1H), 7.99 (d, J = 2.0Hz, 1H),
7.65-7.7 (m, 1H), 7.5-7.6 (m, 3H), 7.4-7.45 (m, 2H), 6.44 (bs, 1H),
4.4-4.6 (m, 2H).
1-018 δ8.52 (d, J = 1.5Hz, 1H), 7.93 (d, J = 1.5Hz, 1H), 7.4-7.7 (m, 6H),
7.0-7.15 (m, 3H), 1.76 (s, 6H).
1-031 δ8.53 (d, J = 1.8Hz, 1H), 7.93 (d, J = 1.8Hz, 1H), 7.5-7.7 (m, 4H),
7.45-7.5 (m, 2H), 7.35-7.4 (m, 2H), 6.50 (t, J = 6.3Hz, 1H),
4.46 (td, J = 13.5, 6.3Hz, 2H), 1.33 (s, 9H).
1-035 δ8.55 (d, J = 1.7Hz, 1H), 7.95 (d, J = 1.7Hz, 1H), 7.5-7.7 (m, 4H),
7.29 (t, J = 7.8Hz, 1H), 7.14 (dt, J = 7.8, 1.5Hz, 1H),
7.06 (dd, J = 2.7, 1.5Hz, 1H), 6.96 (ddd, J = 7.8, 2.7, 1.5Hz, 1H),
6.46 (t, J = 6.3Hz, 1H), 4.47 (td, J = 13.2, 6.3Hz, 2H), 3.84 (s, 3H).
1-062 δ8.5-8.6 (m, 1H), 7.8-7.9 (m, 1H), 7.65-7.7 (m, 1H), 7.45-7.65 (m, 2H),
7.3-7.4 (m, 1H), 6.27 (d, J = 9.9Hz, 1H), 5.2-5.45 (m, 1H),
1.70 (d, J = 19.8Hz, 6H), 1.45 (d, J = 6.8Hz, 3H).
1-064 δ8.58 (d, J = 1.7Hz, 1H), 8.0-8.1 (m, 2H), 7.93 (d, J = 1.7Hz, 1H),
7.8-7.9 (m, 2H), 7.5-7.8 (m, 2H), 6.9-7.0 (m, 2H),
6.36 (d, J = 9.5Hz, 1H), 5.2-5.4 (m, 1H), 3.84 (s, 3H),
1.42 (d, J = 7.2Hz, 3H).
1-074 δ8.4-8.5 (m, 1H), 7.85-7.9 (m, 1H), 7.5-7.7 (m, 4H),
7.27 (d, J = 1.8Hz, 1H), 6.50 (t, J = 6.0Hz, 1H), 6.42 (d, J = 1.8Hz, 1H),
4.4-4.5 (m, 2H), 2.44 (s, 3H).
1-117 δ8.60 (d, J = 1.5Hz, 1H), 7.93 (d, J = 1.5Hz, 1H), 7.75-7.85 (m, 1H),
7.6-7.7 (m, 1H), 7.45-7.6 (m, 2H), 7.25-7.4 (m, 2H), 7.1-7.2 (m, 1H),
6.29 (d, J = 8.9Hz, 1H), 5.2-5.45 (m, 1H), 1.47 (d, J = 7.1Hz, 3H).
2-001 δ8.73 (d, J = 5.1Hz, 1H), 8.59 (d, J = 1.8Hz, 1H), 8.23 (t, J = 6.0Hz, 1H),
8.17 (d, J = 5.1Hz, 1H), 7.93 (d, J = 1.8Hz, 1H), 7.5-7.6 (m, 3H),
7.05-7.15 (m, 2H), 4.4-4.55 (m, 2H).
2-002 δ8.65-8.7 (m, 1H), 8.55-8.6 (m, 1H), 8.4-8.5 (m, 1H), 8.1-8.25 (m, 1H),
7.85-7.9 (m, 1H), 7.75-7.8 (m, 1H), 7.4-7.5 (m, 2H),
7.3-7.4 (m, 2H), 5.15-5.45 (m, 1H), 1.49 (d, J = 6.5Hz, 3H).
2-015 δ8.64 (d, J = 1.8Hz, 1H), 8.42 (ddd, J = 4,5 1.5, 0.6Hz, 1H), 8.11 (bs, 1H),
7.80 (d, J = 1.8Hz, 1H), 7.78 (ddd, J = 8.4, 1.5, 0.6Hz, 1H),
7.51 (td, J = 7.2, 1.8Hz, 1H), 7.3-7.4 (m, 2H), 7.1-7.15 (m, 2H),
3.8-3.9 (m, 3H), 1.34 (d, J = 6.6Hz, 3H).
2-058 δ8.61 (d, J = 1.8Hz, 1H), 8.47 (dd, J = 4.8, 1.8Hz, 1H), 8.15-8.2 (m, 1H),
7.93 (d, J = 1.8Hz, 1H), 7.78 (dd, J = 8.4, 1.8Hz, 1H), 7.65-7.7 (m, 4H),
7.36 (dd, J = 8.4, 1.8Hz, 1H), 5.25-5.4 (m, 1H), 1.50 (d, J = 6.9Hz, 3H).
3-002 δ8.55-8.6 (m, 2H), 8.45-8.5 (m, 1H), 8.1-8.15 (m, 1H),
7.95-8.05 (m, 1H), 7.93 (d, J = 1.8Hz, 1H), 7.3-7.4 (m, 3H),
7.05-7.15 (m, 1H), 4.35-4.6 (m, 2H).
3-018 δ8.80 (dd, J = 4.8, 1.7Hz, 1H), 8.56 (d, J = 1.7Hz, 1H),
8.06 (dd, J = 7.8, 1.7Hz, 1H), 7.94 (d, J = 1.7Hz, 1H),
7.68 (dd, J = 7.8, 4.8Hz, 1H), 7.5-7.6 (m, 2H), 7.05-7.15 (m, 3H),
6.9-7.0 (m, 1H), 4.50 (td, J = 13.2, 6.3Hz, 2H).
3-026 δ8.58 (d, J = 1.8Hz, 1H), 8.46 (dd, J = 4.8, 2.1Hz, 1H),
8.12 (dd, J = 7.5, 2.1Hz, 1H), 7.95 (d, J = 1.8Hz, 1H), 7.45-7.5 (m, 2H),
7.4-7.45 (m, 2H), 7.34 (dd, J = 7.5, 4.8Hz, 1H), 7.32 (bs, 1H),
4.49 (td, J = 13.5, 6.3Hz, 2H), 1.34 (s, 9H).
3-051 δ8.51 (d, J = 1.7Hz, 1H), 8.4-8.45 (m, 1H), 8.1-8.15 (m, 1H),
7.80 (d, J = 1.7Hz, 1H), 7.7-7.75 (m, 1H), 7.45-7.55 (m, 2H),
7.3-7.35 (m, 1H), 7.0-7.1 (m, 2H), 3.92 (d, J = 6.5Hz, 2H),
1.60 (s, 6H).
3-059 δ8.7-8.75 (m, 1H), 8.61 (d, J = 1.7Hz, 1H), 7.97 (d, J = 1.7Hz, 1H),
7.8-7.85 (m, 1H), 7.65 (s, 4H), 7.45-7.5 (m, 1H),
6.86 (t, J = 55.9Hz, 1H), 6.60 (d, J = 9.5Hz, 1H), 5.2-5.45 (m, 1H),
1.50 (d, J = 6.8Hz, 3H).
3-062 δ8.67 and 8.60 (d, J = 1.8Hz, 1H), 8.45-8.5 and 8.35-8.45 (m, 1H),
8.09 and 7.76 (dd, J = 8.0, 2.5Hz, 1H), 7.94 and 6.75 (d, J = 8.0Hz, 1H),
7.85 and 7.82 (d, J = 1.8Hz, 1H), 7.45-7.6 (m, 2H), 7.2-7.4 (m, 1H),
7.0-7.15 (m, 2H), 4.97 and 4.84 (d, J = 2.8Hz, 1H),
4.75-4.9 and 4.7-4.55 (m, 1H), 3.40 and 3.37 (s, 3H),
1.50 and 1.16 (d, J = 6.7Hz, 3H).
3-076 δ8.52 (d, J = 1.8Hz, 1H), 8.45-8.5 (m, 1H), 8.1-8.15 (m, 1H),
7.85-7.9 (m, 1H), 7.34 (dd, J = 8.1, 4.8Hz, 1H), 7.30 (bs, 1H),
7.27 (d, J = 1.8Hz, 1H), 6.42 (d, J = 1.8Hz, 1H), 4.4-4.5 (m, 2H),
2.44 (s, 3H).
5-001 δ8.55-8.6 (m, 1H), 7.95-8.05 (m, 1H), 7.55-7.6 (m, 2H),
7.42 (d, J = 2.1Hz, 1H), 7.25-7.3 (m, 2H), 7.05-7.1 (m, 1H),
6.57 (d, J = 2.1Hz, 1H), 4.43 (td, J = 13.2, 6.6Hz, 2H).
7-007 δ8.54 (d, J = 2.0Hz, 1H), 7.79 (d, J = 2.0Hz, 1H), 7.45-7.6 (m, 2H),
7.35-7.45 (m, 2H), 7.15-7.25 (m, 2H), 7.0-7.15 (m, 1H),
3.4-3.7 (m, 2H), 3.05-3.35 (m, 2H).
7-012 δ8.50 (d, J = 1.7Hz, 1H), 7.86 (d, J = 1.7Hz, 1H), 7.44 (d, J = 5.5Hz, 1H),
7.22 (d, J = 5.5Hz, 1H), 6.86 (d, J = 9.2Hz, 1H), 5.15-5.35 (m, 1H),
1.74 (d, J = 19.8Hz, 6H), 1.46 (d, J = 6.8Hz, 3H).
8-005 δ8.56 (s, 1H), 8.04 (d, J = 8.3Hz, 1H), 7.88 (s, 1H), 7.3-7.7 (m, 2H),
7.15-7.3 (m, 1H), 6.95-7.15 (m, 1H), 6.60 (d, J = 9.8Hz, 1H),
5.15-5.4 (m, 1H), 1.44 (d, J = 6.7Hz, 3H).
9-003 δ8.41 (d, J = 1.7Hz, 1H), 7.83 (s, 1H), 7.73 (d, J = 1.7Hz, 1H),
6.8-6.9 (m, 1H), 6.81 (t, J = 54.0Hz, 1H), 5.15-5.35 (m, 1H),
3.90 (s, 3H), 1.45-1.55 (m, 1H), 1.43 (d, J = 6.0Hz, 3H),
0.9-1.0 (m, 2H), 0.8-0.9 (m, 2H).
9-004 δ8.45-8.6 (m, 1H), 7.75-7.85 (m, 2H), 7.4-7.7 (m, 3H), 7.0-7.1 (m, 2H),
6.7-6.9 (m, 1H), 4.6-4.75 (m, 1H), 3.90 (s, 3H), 3.05-3.3 (m, 2H),
1.25-1.3 (m, 3H).
9-005 δ8.57 (d, J = 2.0Hz, 1H), 7.8-7.85 (m, 2H), 7.45-7.55 (m, 1H),
7.3-7.4 (m, 1H), 7.1-7.2 (m, 2H), 6.95-7.05 (m, 1H),
6.90 (t, J = 53.9Hz, 1H), 4.6-4.75 (m, 1H), 3.91 (s, 3H),
3.1-3.3 (m, 2H), 1.29 (d, J = 6.8Hz, 3H).
9-007 δ8.62 (d, J = 1.5Hz, 1H), 7.97 (d, J = 1.5Hz, 1H), 7.95 (s, 1H),
7.75-7.85 (m, 4H), 7.05-7.1 (m, 1H), 6.77 (t, J = 54.6Hz, 1H),
4.43 (td, J = 12.9, 6.0Hz, 2H), 3.92 (s, 3H).
9-009 δ8.57 (d, J = 1.8Hz, 1H), 7.82 (s, 1H), 7.80 (d, J = 1.8Hz, 1H),
7.4-7.45 (m, 1H), 7.15-7.2 (m, 2H), 6.95-7.0 (m, 1H),
6.89 (t, J = 54.6Hz, 1H), 4.65-4.75 (m, 1H), 3.92 (s, 3H),
3.29 (dd, J = 14.4, 6.9Hz, 1H), 3.17 (dd, J = 14.4, 5.4Hz, 1H),
1.30 (d, J = 6.9Hz, 3H).
9-010 δ8.62 (d, J = 1.8Hz, 1H), 7.95 (d, J = 1.8Hz, 1H), 7.84 (s, 1H),
7.65-7.7 (m, 1H), 7.4-7.45 (m, 2H), 6.80 (t, J = 54.6Hz, 1H),
6.85-6.9 (m, 1H), 5.25-5.35 (m, 1H), 3.90 (s, 3H),
1.46 (d, J = 6.9Hz, 3H).
10-001 δ8.60 (d, J = 2.0Hz, 1H), 7.93 (d, J = 2.0Hz, 1H), 7.5-7.65 (m, 3H),
7.05-7.15 (m, 2H), 4.40 (td, J = 13.5, 6.5Hz, 2H), 2.53 (s, 3H).
11-011 δ8.60 (d, J = 2.1Hz, 1H), 7.96 (d, J = 1.7Hz, 1H), 7.9-7.95 (m, 1H),
7.4-7.5 (m, 1H), 7.15-7.25 (m, 2H), 7.03 (d, J = 9.9Hz, 1H),
5.15-5.4 (m, 1H), 1.49 (d, J = 6.8Hz, 3H).
14-019 δ8.56 (d, J = 1.8Hz, 1H), 7.93 (d, J = 1.8Hz, 1H), 7.45-7.5 (m, 2H),
7.3-7.45 (m, 3H), 6.9-7.0 (m, 2H), 6.65 (t, J = 6.3Hz, 1H),
4.47 (td, J = 13.5, 6.3Hz, 2H), 1.34 (s, 9H).
14-046 δ8.45-8.5 (m, 1H), 7.75-7.8 (m, 1H), 7.45-7.55 (m, 2H),
7.25-7.35 (m, 1H), 6.95-7.15 (m, 3H), 6.85-6.95 (m, 2H),
3.90 (d, J = 6.5Hz, 2H), 1.59 (s, 6H).
16-002 δ8.65-8.9 (m, 1H), 7.85-8.05 (m, 1H), 7.3-7.45 (m, 1H), 7.2-7.3 (m, 2H),
7.0-7.15 (m, 1H), 3.4-3.6 (m, 2H), 1.59 (bs, 2H).
16-011 δ8.62 (d, J = 1.7Hz, 1H), 7.91 (d, J = 1.7Hz, 1H), 7.45-7.55 (m, 2H),
7.35-7.4 (m, 2H), 3.75-4.00 (m, 1H), 1.60 (bs, 2H),
1.24 (d, J = 6.8Hz, 3H).
16-015 δ8.59 (d, J = 1.7Hz, 1H), 7.92 (d, J = 1.7Hz, 1H), 7.25-7.55 (m, 4H),
3.52 (t, J = 14.0Hz, 2H), 1.57 (bs, 2H).
16-018 δ8.6-8.65 (m, 1H), 7.9-7.95 (m, 1H), 7.2-7.35 (m, 4H), 3.45-3.6 (m, 2H),
2.52 (s, 3H), 1.53 (bs, 2H).
16-022 δ8.62 (d, J = 1.5Hz, 1H), 7.93 (d, J = 1.5Hz, 1H), 7.65-7.8 (m, 2H),
7.45-7.65 (m, 2H), 3.3-3.8 (m, 2H), 1.60 (bs, 2H).
16-023 δ8.62 (d, J = 1.5Hz, 1H), 7.95 (d, J = 1.5Hz, 1H), 7.6-7.8 (m, 2H),
7.5-7.6 (m, 2H), 3.4-3.7 (m, 2H), 1.60 (bs, 2H).
16-026 δ8.55-8.6 (m, 1H), 7.9-7.95 (m, 1H), 7.45-7.5 (m, 2H), 6.9-6.95 (m, 2H),
4.3-4.4 (m, 2H), 3.84 (s, 3H).
16-027 δ8.60 (d, J = 1.8Hz, 1H), 7.92 (d, J = 1.8Hz, 1H), 7.55-7.6 (m, 2H),
7.1-7.15 (m, 2H), 6.56 (t, J = 73.8Hz, 1H), 3.52 (t, J = 13.8Hz, 2H),
1.53 (bs, 2H).
16-028 δ8.55-8.6 (m, 1H), 7.9-8.0 (m, 1H), 7.55-7.6 (m, 2H), 7.25-7.3 (m, 2H),
3.45-3.6 (m, 2H), 1.53 (bs, 2H).
16-034 δ8.62 (d, J = 1.8Hz, 1H), 7.95 (d, J = 1.8Hz, 1H), 7.6-7.75 (m, 4H),
3.4-3.7 (m, 2H), 1.60 (bs, 2H).
16-041 δ8.60 and 8.57 (d, J = 2.1Hz, 1H), 8.00 and 7.94 (d, J = 2.1Hz, 1H),
7.3-7.45 (m, 3H), 3.45-3.6 (m, 2H), 1.55 (bs, 2H).
16-043 δ8.56 (d, J = 1.8Hz, 1H), 7.89 (d, J = 1.8Hz, 1H), 7.6-7.75 (m, 1H),
7.45 (t, J = 1.8Hz, 1H), 6.5-6.55 (m, 1H), 3.51 (t, J = 13.8Hz, 2H),
1.55 (bs, 2H).
16-044 δ8.58 (d, J = 1.8Hz, 1H), 7.91 (d, J = 1.8Hz, 1H),
7.40 (dd, J = 5.1, 1.2Hz, 1H), 7.38 (dd, J = 3.6, 1.2Hz, 1H),
7.06 (dd, J = 5.1, 3.6Hz, 1H), 3.52 (t, J = 14.1Hz, 2H), 1.55-1.6 (m, 2H).
16-053 δ8.4-8.45 (m, 1H), 8.00 (d, J = 9.0Hz, 2H), 7.7-7.8 (m, 1H),
7.00 (d, J = 9.0Hz, 2H), 4.25-4.3 (m, 1H), 3.90 (s, 3H), 1.63 (bs, 2H),
1.25 (d, J = 6.6Hz, 3H).
16-054 δ8.65 (d, J = 1.5Hz, 1H), 7.95 (d, J = 1.5Hz, 1H), 7.6-7.75 (m, 4H),
3.75-3.95 (m, 1H), 1.61 (bs, 2H), 1.25 (d, J = 6.6Hz, 3H).
16-060 δ8.6-8.65 (m, 1H), 7.8-7.85 (m, 1H), 7.45-7.5 (m, 2H), 7.35-7.4 (m, 2H),
5.85 (ddd, J = 48.0, 6.9, 4.5Hz, 1H), 3.2-3.45 (m, 2H), 1.57 (bs, 2H).
16-061 δ8.69 (d, J = 1.8Hz, 1H), 7.87 (d, J = 1.8Hz, 1H), 7.45-7.5 (m, 1H),
7.15-7.2 (m, 2H), 5.86 (ddd, J = 48.0, 6.9, 4.5Hz, 1H), 3.2-3.4 (m, 2H),
1.56 (bs, 2H).
16-064 δ8.5-8.55 (m, 1H), 7.85-7.9 (m, 1H), 7.31 (d, J = 1.8Hz, 1H),
6.43 (d, J = 1.8Hz, 1H), 3.51 (t, J = 14.1Hz, 2H), 2.45 (s, 3H),
1.55 (bs, 2H).
16-065 δ8.55 (d, J = 1.8Hz, 1H), 7.88 (d, J = 1.8Hz, 1H), 7.38 (d, J = 1.5Hz, 1H),
6.85-6.9 (m, 1H), 3.51 (t, J = 14.1Hz, 2H), 2.49 (d, J = 1.2Hz, 3H),
1.55 (bs, 2H).
16-066 δ8.60 (d, J = 1.8Hz, 1H), 7.92 (d, J = 1.8Hz, 1H), 7.38 (d, J = 2.4Hz, 1H),
6.51 (d, J = 2.4Hz, 1H), 3.95 (s, 3H), 3.51 (t, J = 14.1Hz, 2H),
1.54 (bs, 2H).
16-067 δ8.65-8.7 (m, 2H), 8.00 (d, J = 1.5Hz, 1H), 7.75 (td, J = 7.8, 1.5Hz, 1H),
7.55-7.6 (m, 1H), 7.33 (ddd, J = 7.8, 4.8, 1.5Hz, 1H),
3.52 (t, J = 14.1Hz, 2H), 1.57 (bs, 2H).
16-072 δ8.6-8.65 (m, 1H), 7.81 (d, J = 1.8Hz, 1H), 7.52 (td, J = 7.2, 1.8Hz, 1H),
7.3-7.4 (m, 1H), 7.1-7.15 (m, 2H), 3.45-3.6 (m, 1H), 2.9-3.0 (m, 2H),
1.63 (bs, 2H), 1.27 (d, J = 6.9Hz, 3H).
16-073 δ8.66 (d, J = 1.5Hz, 1H), 7.95 (d, J = 1.5Hz, 1H),
7.54 (td, J = 7.2, 1.8Hz, 1H), 7.35-7.45 (m, 1H), 7.1-7.3 (m, 2H),
3.75-3.95 (m, 1H), 1.57 (bs, 2H), 1.25 (d, J = 6.6Hz, 3H).
16-074 δ8.66 (d, J = 1.5Hz, 1H), 7.95 (d, J = 1.5Hz, 1H), 7.65-7.7 (m, 4H),
3.8-3.95 (m, 1H), 1.56 (bs, 2H), 1.25 (d, J = 6.9Hz, 3H).
16-078 δ8.55 (d, J = 1.8Hz, 1H), 7.79 (d, J = 1.8Hz, 1H), 7.3-7.4 (m, 2H),
7.2-7.3 (m, 1H), 7.05-7.1 (m, 1H), 3.05-3.2 (m, 4H).
16-100 δ8.55-8.6 (m, 1H), 7.80 (d, J = 2.4Hz, 1H), 7.45-7.5 (m, 2H),
7.3-7.4 (m, 2H), 2.95-3.05 (m, 2H), 1.0-1.05 (m, 4H).
16-101 δ8.58 (d, J = 1.8Hz, 1H), 7.80 (d, J = 1.2Hz, 1H), 7.4-7.5 (m, 1H),
7.15-7.2 (m, 2H), 3.5-3.55 (m, 1H), 2.9-3.1 (m, 2H), 1.94 (bs, 2H),
1.22 (d, J = 6.0Hz, 3H).
16-102 δ8.64 (d, J = 1.7Hz, 1H), 7.93 (d, J = 1.7Hz, 1H), 7.45-7.6 (m, 1H),
6.85-6.95 (m, 2H), 3.89 (bs, 1H), 1.15-1.3 (m, 5H).
16-106 δ8.62 (d, J = 1.8Hz, 1H), 7.90 (d, J = 1.8Hz, 1H), 7.4-7.45 (m, 1H),
7.25-7.3 (m, 1H), 7.15-7.2 (m, 1H), 3.8-3.9 (m, 1H), 2.49 (s, 3H),
1.57 (bs, 2H), 1.25 (d, J = 6.0Hz, 3H).
16-107 δ8.68 (d, J = 1.8Hz, 1H), 7.97 (d, J = 1.8Hz, 1H), 7.6-7.7 (m, 1H),
7.4-7.5 (m, 2H), 3.8-3.9 (m, 1H), 1.59 (bs, 2H),
1.25 (d, J = 6.9Hz, 3H).
16-108 δ8.63 (d, J = 0.9Hz, 1H), 7.92 (d, J = 0.9Hz, 1H), 7.35-7.4 (m, 1H),
7.1-7.15 (m, 2H), 3.95 (s, 3H), 3.8-3.9 (m, 1H), 1.56 (bs, 2H),
1.25 (d, J = 7.2Hz, 3H).
16-111 δ8.66 (d, J = 1.5Hz, 1H), 7.96 (d, J = 1.5Hz, 1H), 7.0-7.05 (m, 2H),
3.8-3.95 (m, 1H), 1.67 (bs, 2H), 1.25 (d, J = 6.0Hz, 3H).
17-020 δ8.60 (d, J = 1.7Hz, 1H), 7.88 (d, J = 1.7Hz, 1H), 7.65-7.75 (m, 1H),
7.4-7.55 (m, 2H), 7.3-7.4 (m, 2H), 4.6-4.85 (m, 1H),
1.36 (d, J = 6.5Hz, 3H), 1.90 (s, 9H).
17-021 δ8.55-8.6 (m, 1H), 7.85-7.9 (m, 1H), 7.6-7.75 (m, 1H),
7.45-7.55 (m, 2H), 6.85-6.95 (m, 2H), 4.55-4.85 (m, 1H), 3.85 (s, 3H),
1.36 (d, J = 6.4Hz, 3H), 1.31 (s, 9H).
17-022 δ8.63 (d, J = 1.5Hz, 1H), 7.92 (d, J = 1.5Hz, 1H), 7.6-7.7 (m, 5H),
4.6-4.9 (m, 1H), 1.37 (d, J = 6.4Hz, 3H), 1.30 (s, 9H).
17-029 δ8.57 (d, J = 1.8Hz, 1H), 7.91 (d, J = 1.8Hz, 1H), 7.45-7.5 (m, 2H),
7.35-7.4 (m, 2H), 5.12 (t, J = 6.3Hz, 1H), 4.09 (td, J = 13.2, 6.3Hz, 2H),
1.41 (s, 9H), 1.34 (s, 9H).
17-035 δ8.62 (d, J = 1.2Hz, 1H), 7.95-8.0 (m, 3H), 7.7-7.75 (m, 2H),
5.08 (t, J = 6.3Hz, 1H), 4.10 (td, J = 13.5, 6.3Hz, 2H), 3.09 (s, 3H),
1.41 (s, 9H).
17-043 δ8.54 (d, J = 1.8Hz, 1H), 7.88 (d, J = 1.8Hz, 1H),
7.76 (dd, J = 1.8, 0.6Hz, 1H), 7.45 (t, J = 1.8Hz, 1H),
6.55 (dd, J = 1.8, 1.6Hz, 1H), 5.10 (bs, 1H), 4.05-4.15 (m, 2H),
1.41 (s, 9H).
17-045 δ8.60 (d, J = 1.8Hz, 1H), 7.94 (d, J = 1.8Hz, 1H), 7.50 (s, 1H),
5.09 (bs, 1H), 4.05-4.15 (m, 2H), 2.76 (s, 3H), 1.40 (s, 9H).
17-064 δ8.53 (d, J = 1.8Hz, 1H), 7.86 (d, J = 1.8Hz, 1H), 7.27 (d, J = 1.8Hz, 1H),
6.43 (d, J = 1.8Hz, 1H), 5.10 (bs, 1H), 4.08 (td, J = 13.2, 6.6Hz, 2H),
2.44 (s, 3H), 1.41 (s, 9H).
17-065 δ8.53 (d, J = 1.8Hz, 1H), 7.87 (d, J = 1.8Hz, 1H), 7.37 (d, J = 1.2Hz, 1H),
6.85-6.9 (m, 1H), 5.09 (bs, 1H), 4.08 (td, J = 13.8, 7.2Hz, 2H),
2.49 (d, J = 0.9Hz, 3H), 1.41 (s, 9H).
17-066 δ8.59 (d, J = 1.8Hz, 1H), 7.92 (d, J = 1.8Hz, 1H), 7.39 (d, J = 2.4Hz, 1H),
6.52 (d, J = 2.4Hz, 1H), 5.09 (bs, 1H), 4.05-4.15 (m, 2H), 3.96 (s, 3H),
1.41 (s, 9H).
17-067 δ8.65-8.7 (m, 2H), 7.99 (d, J = 1.8Hz, 1H), 7.74 (td, J = 7.5, 1.8Hz, 1H),
7.55-7.6 (m, 1H), 7.33 (ddd, J = 7.5, 5.1, 1.2Hz, 1H), 5.09 (bs, 1H),
4.09 (td, J = 13.8, 6.9Hz, 2H), 1.40 (s, 9H).
17-071 δ8.59 (d, J = 1.8Hz, 1H), 7.80 (d, J = 1.8Hz, 1H),
7.52 (td, J = 7.2, 1.8Hz, 1H), 7.35-7.4 (m, 1H), 7.1-7.15 (m, 2H),
4.90 (bs, 1H), 3.65-3.7 (m, 1H), 3.5-3.55 (m, 2H), 1.42 (s, 9H),
1.24 (d, J = 6.6Hz, 3H).
17-077 δ8.56 (d, J = 1.8Hz, 1H), 7.78 (d, J = 1.8Hz, 1H), 7.3-7.4 (m, 2H),
7.2-7.25 (m, 1H), 7.05-7.1 (m, 1H), 5.15 (bs, 1H), 3.55-3.6 (m, 2H),
3.05-3.15 (m, 2H), 1.43 (s, 9H).
17-095 δ8.53 (d, J = 1.8Hz, 1H), 7.87 (d, J = 1.8Hz, 1H), 6.86 (s, 1H),
5.10 (t, J = 6.3Hz, 1H), 4.08 (td, J = 13.5, 6.3Hz, 2H), 2.52 (s, 3H),
1.41 (s, 9H).
17-098 δ8.57 (d, J = 1.8Hz, 1H), 7.79 (d, J = 1.8Hz, 1H), 7.4-7.5 (m, 1H),
7.15-7.2 (m, 2H), 4.95-5.0 (m, 1H), 4.15-4.25 (m, 1H),
3.05-3.1 (m, 2H), 1.38 (s, 9H), 1.22 (d, J = 6.9Hz, 3H).
――――――――――――――――――――――――――――――――――――――――
[Test example]
Next, the usefulness of the compound of the present invention as a pest control agent will be specifically described in the following test examples, but the present invention is not limited to these.

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

  Preparation of test drug solution B: The compound of the present invention was dissolved in dimethyl sulfoxide to prepare a 1% strength solution. This chemical solution was diluted to a predetermined concentration and used in the following Test Example 9 to Test Example 13 and a comparative test.

Test Example 1 Cucumber powdery mildew prevention effect test Cucumber (variety: Sagamihanjiro) was planted in a 90 cm ³ plastic pot, and the test drug solution A of the present compound was diluted to a concentration of 500 ppm by adding distilled water at the cotyledon stage. 5 ml sprayed per pot. After air drying, the cucumber was placed in an air-conditioned greenhouse (20 ° C.) and sprayed with a conidial spore suspension of cucumber powdery mildew (Erysiphe polygoni, Synonym; Erysiphe betae). After 9 days at the same temperature, the proportion of the lesions formed in the inoculated leaves was measured, and the control value was calculated according to the following formula. In addition, the test was performed by 2 continuous systems.

Control value = [1- (treatment area lesion area ratio / non-treatment area lesion area ratio)] × 100
As a result, among the tested compounds, the following compounds showed a control value of 70% or more.
Compound of the present invention: No.1-002,1-005,1-006,1-007,1-011,1-012,1-016,1-019,1-022,1-023,1-031, 1-038,1-042,1-044,1-045,1-046,1-048,1-049,1-050,1-051,1-052,1-059,1-060,1- 061,1-062,1-063,1-066,1-067,1-068,1-069 ^* , 1-070,1-073,1-074,1-086,1-108,1-114 , 1-116,1-121,2-002,2-008,2-011,2-016,2-018,2-054,2-055,2-056,2-058,2-059,2 -067,3-002 ^* , 3-010,3-012,3-014,3-025,3-036,3-037,3-043,3-051,3-053,3-059,3- 062,3-063,3-064,3-065,3-066,3-067,3-084,3-085,3-088,3-089,3-104,3-142,3-146, 3-147,3-148,3-150,4-008,4-009,7-004,7-005 ^* , 7-006 ^* , 7-007,7-009,7-010,7-012, 7-013,7-019,7-021,8-001 ^* , 8-002,8-004,8-005,9-002,9-003,9-004,9-005,9-006,9 -010,11-001,12-001,15-001.

In addition, the said ^* mark represents having implemented the test using a 100 ppm concentration chemical | medical solution.

Test example 2 Cucumber gray mold prevention effect test (spore inoculation)
Cucumber (variety: Sagamihanjiro) was planted in a 90 cm ³ plastic pot, and at the cotyledon stage, the test drug solution A of the compound of the present invention was diluted with distilled water to a concentration of 500 ppm and sprayed with 5 ml per pot. After air drying, the treated leaves were cut out and placed in a plastic container. A conidial spore suspension of cucumber gray mold fungus (Botrytis cinerea) and a dissolved PDA medium were mixed at a ratio of 1: 1, and 30 μl of the treated leaves were inoculated dropwise. After inoculation, after placing it at 20 ° C. under high humidity for 3 days, the ratio of the formed lesions to the inoculated leaves was measured, and the control value was calculated from the same formula as in Test Example 1. In addition, the test was performed by 2 continuous systems.

As a result, among the tested compounds, the following compounds showed a control value of 70% or more.
Compound of the present invention: No.1-002,1-003,1-004,1-006,1-007,1-009,1-011,1-012,1-015,1-016,1-019, 1-023,1-027,1-028,1-029,1-030,1-031,1-033,1-034,1-036,1-037,1-038,1-042,1- 045,1-046,1-047,1-048,1-049,1-050,1-051,1-052,1-054,1-055,1-056,1-057,1-061, 1-062,1-063,1-066,1-067,1-068,1-069 ^* , 1-070,1-071,1-073,1-074,1-075,1-083,1 -086,1-087,1-088,1-090,1-091,1-093,1-094,1-097,1-106,1-108,1-109,1-110,1-111 , 1-112,1-113,1-115,1-116,1-117,1-119,1-120,1-121,1-125,2-002,2-007,2-008,2 -010,2-011,2-016,2-017,2-018,2-019,2-020,2-031,2-032,2-033,2-044,2-045,2-055 , 2-056,2-057,2-058,2-059,2-060,2-061,2-062,2-063,2-064,2-065,2-066,2-067,3 -002 ^* , 3-003,3-004,3-007,3-009,3-010,3-011,3-012,3-014,3-015,3-018,3-021,3- 023,3-025,3-026,3-029,3-030,3-031,3-032,3-033,3-035,3-036,3-037,3-038,3-039, 3-040,3-041,3-042,3-043,3-044,3-045,3-047,3-049,3-050,3-053,3-054,3-055,3- 058,3-059,3-062,3-063,3-064,3-065,3-066,3-067,3-068,3-070,3-071,3-074,3-076, 3-078,3-084,3-085,3-088,3-089,3-090,3-091,3-092,3-093,3-094,3-095,3-096,3- 098, 3-099,3-100,3-101,3-102,3-103,3-104,3-105,3-106,3-107,3-109,3-110,3-111,3- 117, 3-118, 3-121, 3-122, 3-123, 3-124, 3-129, 3-130, 3-131, 3-132, 3-133, 3-134, 3-135, 3-136, 3-137, 3-138, 3-139, 3-140, 3-141, 3-142, 3-144, 3-145, 3-146, 3-147, 3-148, 3- 149,3-150,3-151,3-152,3-153,4-002,4-003,4-004,4-005,4-006,4-007,4-008,4-009, 6-001,7-001,7-004,7-006 ^* , 7-007,7-010,7-012,7-013,7-018,7-019,7-021,7-022,8 -001 ^* , 8-002,8-003 ^* , 8-004,8-005,9-001 ^* , 9-002,9-003,9-004,9-005,9-006,9-007, 9-009,9-010,14-038.

In addition, the said ^* mark represents having implemented the test using a 100 ppm concentration chemical | medical solution.

Test example 3 Cucumber gray mold prevention effect test (mycelia inoculation)
Cucumber (variety: Sagamihanjiro) was planted in a 90 cm ³ plastic pot, and at the cotyledon stage, the test drug solution A of the compound of the present invention was diluted with distilled water to a concentration of 500 ppm and sprayed with 5 ml per pot. One day later, the pot was placed in a plastic container and inoculated into a cucumber cotyledon treated with a drug containing bacterial agar pieces (diameter 5 mm) of cucumber gray mold (Botrytis cinerea) previously cultured in PDA medium. After inoculation, the plastic container is covered with plastic, humidified, and left at 20 ° C for 2 days. Then, the proportion of the lesions formed in the inoculated leaves is measured, and the control value is calculated from the same formula as in Test Example 1. did. In addition, the test was performed by 2 continuous systems.

As a result, among the tested compounds, the following compounds showed a control value of 70% or more.
Compound of the present invention: No.1-002,1-003,1-006,1-007,1-009,1-012,1-015,1-016,1-017 ^* , 1-019,1-038 , 1-042,1-044,1-045,1-046,1-049,1-050,1-051,1-052,1-062,1-063,1-067,1-068,1 -070,1-071,1-073,1-074,1-076,1-081,1-089,1-090,1-091,1-094,1-097,1-106,1-108 , 1-109,1-116,1-117,2-002,2-007,2-016,2-018,2-019,2-020,2-056,2-057,2-058,2 -059,2-062,2-065,2-066,2-067,3-003,3-004,3-006,3-007,3-010,3-011,3-012,3-014 , 3-025,3-026,3-030,3-031,3-035,3-036,3-037,3-038,3-040,3-041,3-042,3-043,3 -044,3-053,3-054,3-058,3-059,3-062,3-063,3-064,3-065,3-066,3-067,3-070,3-074 , 3-084,3-085,3-088,3-089,3-091,3-093,3-094,3-095,3-102,3-103,3-104,3-106,3 -117, 3-118, 3-121, 3-130, 3-134, 3-135, 3-140, 3-141, 3-142, 3-146, 3-147, 3-150, 4-003 , 4-004,4-005,4-006,4-007,4-008,4-009,6-001,7-004,7-006 ^* , 7-010,7-012,7-015, 7-021,7-022,8-001 ^* , 8-002,8-003 ^* , 8-004,8-005,9-001 ^* , 9-002,9-003,9-004,9-005 , 9-006,9-007,9-009,9-010,12-001.

In addition, the said ^* mark represents having implemented the test using a 100 ppm concentration chemical | medical solution.

Test Example 4 Cucumber Nucleus Disease Prevention Effect Test Cucumber (variety: Sagamihanjiro) was planted in a 90 cm ³ plastic pot, and the test drug solution A of the compound of the present invention was diluted to a concentration of 500 ppm by adding distilled water at the cotyledon stage. 5 ml sprayed per pot. After air-drying, the pot was placed in a plastic container and inoculated into a cucumber cotyledon treated with a drug, a garnish containing agar (Sclerotinia sclerotiorum) -containing agar pieces (diameter 5 mm) previously cultured in a PDA medium. After inoculation, the plastic container is covered with plastic, humidified, and left at 20 ° C for 2 days. Then, the proportion of the lesions formed in the inoculated leaves is measured, and the control value is calculated from the same formula as in Test Example 1. did. In addition, the test was performed by 2 continuous systems.

As a result, among the tested compounds, the following compounds showed a control value of 70% or more.
Compound of the present invention: No.1-001,1-002,1-003,1-004,1-005,1-006,1-007,1-009,1-010,1-011,1-012, 1-015,1-016,1-017 ^* , 1-019,1-021,1-022,1-023,1-025,1-026,1-027,1-028,1-029,1 -030,1-031,1-033,1-034,1-036,1-037,1-038,1-042,1-043,1-044,1-045,1-046,1-047 , 1-048,1-049,1-050,1-051,1-052,1-053,1-054,1-055,1-056,1-057,1-059,1-060,1 -061,1-062,1-063,1-066,1-067,1-068,1-069 ^* , 1-070,1-071,1-072,1-073,1-074,1- 075,1-076,1-077,1-078,1-079,1-080,1-081,1-082,1-083,1-086,1-087,1-088,1-089, 1-090,1-091,1-092,1-093,1-094,1-095,1-097,1-099,1-102,1-103,1-106,1-108,1- 109,1-110,1-111,1-112,1-113,1-114,1-115,1-116,1-117,1-118,1-119,1-120,1-121, 1-125,2-002,2-007,2-008,2-009,2-010,2-011,2-012,2-014,2-016,2-017,2-018,2- 019,2-020,2-022,2-025,2-027,2-028,2-031,2-032,2-033,2-035,2-037,2-038,2-040, 2-044,2-045,2-046,2-047,2-048,2-050,2-054,2-055,2-056,2-057,2-058,2-059,2- 060,2-061,2-062,2-063,2-064,2-065,2-066,2-067,3-001,3-002 ^* , 3-003,3-004,3-006 , 3-007,3-009,3-010,3-011,3-012,3-014,3-015,3-018,3-019,3-020,3-021,3-022,3 -023,3-024,3-025,3-026,3-027,3-028,3-029,3-030,3-031,3-032,3-033,3-035,3-036 , 3-037,3-038,3-039,3-040,3-041,3-042,3-043,3-044,3-045,3-046,3-047,3-048,3 -049,3-050,3-052,3-053,3-054,3-055,3-056,3-058,3-059,3-061,3-062,3-063,3-064 , 3-065,3-066,3-067,3-068,3-069,3-070,3-071,3-072,3-074,3-075,3-076,3-078,3 -079,3-084,3-085,3-086,3-088,3-089,3-090,3-091,3-092,3-093,3-094,3-095,3-096 , 3-098,3-099,3-100,3-101,3-102,3-103,3-104,3-105,3-106,3-107,3-109,3-110,3 -111, 3-112, 3-113, 3-116, 3-117, 3-118, 3-119, 3-121, 3-122, 3-123, 3-124, 3-125, 3-129 , 3-130, 3-131, 3-132, 3-133, 3-134, 3-135, 3-136, 3-137, 3-138, 3-139, 3-140, 3-141, 3 -142, 3-143, 3-144, 3-145, 3-146, 3-147, 3-148, 3-149, 3-150, 3-151, 3-152, 3-153,4-001 ^* , 4-002,4-003,4-004,4-005,4-006,4-007,4-008,4-009,5-001,6-001,6-002,6-003, 7-001,7-003,7-004,7-006 ^* , 7-007,7-009,7-010,7-011,7-012,7-013,7-014,7-015,7 -016,7-018,7-019,7-021,7-022,8-001 ^* , 8-002,8-003 ^* , 8-004,8-005,9-001 ^* , 9-002, 9-003,9-004,9-005,9-006,9-007,9-009,9-010,12-001,12-002,13-001,14-002,14-007,14- 00 9,14-012,14-032,14-037,14-038,14-041,15-001.

In addition, the said ^* mark represents having implemented the test using a 100 ppm concentration chemical | medical solution.

Test Example 5 Cucumber Anthrax Preventive Effect Test Cucumber (variety: Sagamihanjiro) was planted in a 90 cm ³ plastic pot, and test chemical solution A of the compound of the present invention was diluted to a concentration of 500 ppm by adding distilled water at the cotyledon stage. 5 ml spraying treatment was performed. One day later, a conidial spore suspension of cucumber anthracnose fungus (Colletotrichum lagenarium, Synonym; Colletotrichum orbiculare) was spray-inoculated and placed in an inoculation box at a temperature of 25 ° C. and a humidity of 100% for 2 days. Then, after placing it in an air-conditioned greenhouse (23 ° C.) for 7 days at the same temperature, the proportion of the formed lesions in the inoculated leaves was measured, and the control value was calculated from the same calculation formula as in Test Example 1. . In addition, the test was performed by 2 continuous systems.

As a result, among the tested compounds, the following compounds showed a control value of 70% or more.
Compound of the present invention: No.1-054,1-084,1-066,1-067,1-070,1-092,1-113,1-115,2-006,2-007,2-011, 2-032,2-058,2-059,3-002 ^* , 3-024,3-030,3-048,3-053,3-059,3-065,3-081,3-083,3 -117,3-138,3-139,3-140,3-142,3-143,4-002,4-004,4-006,4-007,7-013,7-018,8-004 , 8-005,9-005,13-003,14-007,14-011,14-027.

In addition, the said ^* mark represents having implemented the test using a 100 ppm concentration chemical | medical solution.

Test Example 6 Wheat powdery mildew prevention effect test 1.3 Test chemical solution A of the compound of the present invention was added to distilled water in a 90 cm ³ plastic pot planted with 1.3 leaves of wheat (variety: Norin 61), and the concentration was 500 ppm. And 5 ml sprayed per pot. One day after spraying, the pot was placed in an air-conditioned greenhouse (20 ° C.), and wheat was inoculated with conidia of wheat powdery mildew (Blumeria graminis f. Sp. Tritici). Thereafter, it was held for 7 days, the ratio of the formed lesions to the inoculated leaves was measured, and the control value was calculated from the same formula as in Test Example 1. In addition, the test was performed by 2 continuous systems.

As a result, among the tested compounds, the following compounds showed a control value of 70% or more.
Compound of the present invention: No.1-001,1-002,1-004,1-005,1-006,1-007,1-009,1-011,1-013,1-015,1-016, 1-017 ^* , 1-019, 1-021, 1-022, 1-023, 1-025, 1-027, 1-028, 1-030, 1-031, 1-034, 1-036, 1 -037,1-038,1-039,1-042,1-044,1-045,1-046,1-047,1-048,1-049,1-050,1-051,1-052 , 1-053,1-054,1-056,1-057,1-058,1-059,1-060,1-061,1-062,1-063,1-066,1-067,1 -068,1-069 ^* , 1-070,1-071,1-072,1-073,1-074,1-076,1-079,1-080,1-081,1-086,1- 087,1-089,1-093,1-094,1-095,1-096,1-097,1-099,1-108,1-110,1-111,1-112,1-114, 1-115,1-116,1-117,1-119,1-120,1-121,1-125,2-002,2-003,2-005,2-007,2-008,2- 009,2-010,2-011,2-015,2-016,2-017,2-018,2-019,2-020,2-031,2-032,2-045,2-054, 2-055,2-056,2-057,2-058,2-059,2-060,2-061,2-062,2-063,2-065,2-066,2-067,3- 002 ^* , 3-003,3-004,3-006,3-007,3-010,3-011,3-012,3-014,3-020,3-025,3-026,3-028 , 3-030,3-031,3-035,3-036,3-037,3-038,3-039,3-040,3-041,3-042,3-043,3-045,3 -049,3-050,3-052,3-053,3-054,3-055,3-058,3-059,3-062,3-063,3-064,3-065,3-066 , 3-067,3-068,3-070,3-074,3-075,3-078,3-084,3-085,3-088,3-089,3-091,3-092,3 -093, 3-094, 3-104, 3-106, 3-107, 3-109, 3-117, 3-131, 3-132, 3-133, 3-136, 3-137, 3-138 , 3-140, 3-141, 3-142, 3-143, 3-146, 3-147, 3-148, 3-150, 3-151, 3-153,4-001 ^* , 4-002, 4-003,4-004,4-006,4-007,4-008,4-009,6-002,7-001,7-004,7-006 ^* , 7-007,7-009,7 -010,7-012,7-013,7-014,7-015,7-018,7-019,7-021,7-022,8-002,8-003 ^* , 8-004,8- 005,9-002,9-003,9-004,9-005,9-006,9-010,12-001,12-002,14-009,14-013,14-014,14-023, 14-032,15-001.

In addition, the said ^* mark represents having implemented the test using a 100 ppm concentration chemical | medical solution.

Test Example 7 Wheat Blight Prevention Effect Test 1.3 Distilled water was added to test chemical solution A of the present invention in a 90 cm ³ plastic pot planted with ³ leaf stage wheat (variety: Haruyutaka) to a concentration of 500 ppm. Then, 5 ml per pot was sprayed. One day after spraying, a conidial spore suspension of wheat blight fungus (Phaeosphaeria nodorum, Synonym; Septoria nodorum) was spray-inoculated on wheat and placed in an inoculation box at a temperature of 20 ° C. and a humidity of 100% for 2 days. Thereafter, it was placed in an air-conditioned greenhouse (20 ° C.) and held for 6 days. The ratio of the formed lesions to the inoculated leaves was measured, and the control value was calculated from the same calculation formula as in Test Example 1. In addition, the test was performed by 2 continuous systems.

As a result, among the tested compounds, the following compounds showed a control value of 70% or more.
Compound of the present invention: No.1-002,1-004,1-006,1-007,1-009,1-010,1-012,1-015,1-017 ^* , 1-031,1-042 , 1-045,1-049,1-050,1-051,1-052,1-057,1-060,1-062,1-063,1-066,1-073,1-074,1 -087,2-002,2-007,2-015,2-016,2-018,2-020,2-056,3-002 ^* , 3-006,3-010,3-011,3- 012,3-014,3-025,3-026,3-036,3-040,3-041,3-042,3-043,3-044,3-051,3-053,3-054, 3-059,3-062,3-070,3-084,3-085,3-088,3-089,3-138,7-001,7-006 ^* , 7-010,7-012,7 -013,8-003 ^* , 8-004,8-005,9-001 ^* , 9-002,9-003,9-004,9-005,9-006,9-010,14-003,14 -009,15-001.

In addition, the said ^* mark represents having implemented the test using a 100 ppm concentration chemical | medical solution.

Test Example 8 Wheat Red Rust Prevention Effect Test 1.3 Into a 90 cm ³ plastic pot planted with ³ leaf stage wheat (variety: Norin 61), distilled water was added to the test chemical solution A of the present invention to a concentration of 500 ppm. Diluted and sprayed 5 ml per pot. One day after spraying, the spore suspension of wheat rust (Puccinia recondita) was spray-inoculated on wheat and placed in an inoculation box at a temperature of 20 ° C. and a humidity of 100% for 1 day. Thereafter, it was placed in an air-conditioned greenhouse (20 ° C.) and held for 8 days. The ratio of the formed lesions to the inoculated leaves was measured, and the control value was calculated from the same calculation formula as in Test Example 1. In addition, the test was performed by 2 continuous systems.

As a result, among the tested compounds, the following compounds showed a control value of 70% or more.
The present compound: No. 3-053, 3-059, 3-083,4-004, 8-005, 9-003, 9-004.

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

Efficacy (%) = [1- (processed microbial flora area ratio / untreated ward flora area ratio)] × 100
As a result, among the tested compounds, the following compounds showed an efficiency (%) of 50% or more.
Compound of the present invention: No.1-002,1-003,1-006,1-007,1-009,1-011,1-012,1-013,1-014,1-015,1-016, 1-017,1-019,1-020,1-022,1-023,1-025,1-026,1-027,1-028,1-031,1-033,1-034,1- 035,1-037,1-038,1-039,1-042,1-045,1-046,1-047,1-048,1-049,1-050,1-051,1-052, 1-053,1-054,1-055,1-056,1-057,1-058,1-059,1-060,1-061,1-062,1-063,1-065,1- 066,1-067,1-068,1-069,1-070,1-071,1-073,1-074,1-076,1-079,1-080,1-081,1-083, 1-086,1-087,1-088,1-089,1-093,1-095,1-096,1-097,1-098,1-100,1-108,1-113,1- 114,1-115,1-116,1-117,1-118,1-120,1-125,2-001,2-002,2-005,2-007,2-008,2-009, 2-010,2-011,2-012,2-014,2-015,2-016,2-017,2-018,2-019,2-020,2-021,2-022,2- 023,2-025,2-027,2-028,2-031,2-032,2-034,2-038,2-040,2-051,2-053,2-054,2-055, 2-056,2-057,2-058,2-059,2-060,2-061,2-062,2-063,2-064,2-066,3-001,3-002,3- 003,3-004,3-006,3-007,3-009,3-010,3-011,3-012,3-013,3-014,3-015,3-016,3-017, 3-018,3-021,3-022,3-023,3-026,3-027,3-028,3-029,3-030,3-031,3-032,3-033,3- 035,3-036,3-037,3-038,3-039,3-040,3-041,3-042,3-043,3-044,3-045,3-047,3-048, 3-049,3-05 0,3-051,3-052,3-053,3-054,3-055,3-056,3-057,3-058,3-059,3-060,3-061,3-062, 3-063, 3-064, 3-065, 3-066, 3-067, 3-068, 3-069, 3-070, 3-071, 3-073, 3-074, 3-075, 3- 076,3-077,3-078,3-081,3-082,3-083,3-084,3-085,3-086,3-087,3-088,3-089,3-090, 3-091,3-092,3-093,3-094,3-096,3-097,3-098,3-099,3-100,3-101,3-102,3-103,3- 104,3-105,3-106,3-109,3-110,3-111,3-112,3-113,3-115,3-116,3-117,3-118,3-121, 3-123, 3-125, 3-133, 3-139, 3-140, 3-141, 3-142, 3-143, 3-144, 3-145, 3-146, 3-147, 3- 148,3-149,3-150,3-152,4-001,4-002,4-003,4-004,4-005,4-006,4-007,4-008,4-009, 5-001,6-001,6-002,7-002,7-003,7-004,7-006,7-007,7-010,7-012,7-013,7-017,7- 018,7-019,7-020,7-021,7-022,8-001,8-002,8-003,8-004,8-005,9-001,9-003,9-004, 9-005,9-006,9-007,12-001,13-001,13-002,14-002,14-009,14-048,14-049.

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

Efficacy (%) = [(number of untreated eggs treated + number of inactive larvae) / number of untreated group active larvae] x 100
As a result, among the tested compounds, the following compounds showed an efficiency (%) of 50% or more.
Compound of the present invention: No.1-002,1-003,1-004,1-006,1-007,1-009,1-011,1-013,1-014,1-015,1-016, 1-017,1-018,1-019,1-020,1-021,1-022,1-023,1-025,1-026,1-027,1-028,1-029,1- 030,1-031,1-034,1-035,1-036,1-037,1-038,1-039,1-042,1-044,1-045,1-046,1-047, 1-048,1-049,1-050,1-051,1-052,1-053,1-054,1-055,1-056,1-058,1-059,1-060,1- 061,1-062,1-063,1-065,1-066,1-068,1-069,1-070,1-071,1-072,1-073,1-074,1-075, 1-076,1-080,1-086,1-087,1-089,1-090,1-091,1-092,1-094,1-095,1-096,1-097,1- 098,1-099,1-100,1-103,1-106,1-107,1-108,1-109,1-110,1-111,1-112,1-114,1-115, 1-116,1-117,1-118,1-119,1-121,1-125,2-001,2-002,2-003,2-005,2-007,2-008,2- 009,2-010,2-011,2-013,2-014,2-016,2-017,2-018,2-019,2-021,2-022,2-025,2-027, 2-028,2-029,2-030,2-031,2-032,2-041,2-044,2-045,2-047,2-050,2-051,2-054,2- 055,2-057,2-058,2-059,2-060,2-062,2-063,2-064,2-065,2-066,2-067,3-001,3-002, 3-003,3-004,3-006,3-007,3-009,3-010,3-011,3-012,3-013,3-014,3-015,3-018,3- 020,3-021,3-022,3-023,3-024,3-025,3-026,3-028,3-029,3-031,3-032,3-033,3-035, 3-036,3-03 7,3-038,3-039,3-040,3-041,3-042,3-043,3-044,3-045,3-046,3-047,3-048,3-050, 3-051,3-052,3-053,3-054,3-055,3-056,3-057,3-058,3-059,3-061,3-062,3-064,3- 065,3-066,3-067,3-068,3-069,3-070,3-071,3-073,3-074,3-075,3-076,3-077,3-078, 3-084,3-086,3-087,3-088,3-089,3-091,3-092,3-093,3-094,3-095,3-096,3-098,3- 099,3-100,3-104,3-105,3-106,3-107,3-109,3-110,3-111,3-101,3-102,3-112,3-113, 3-114, 3-116, 3-117, 3-118, 3-119, 3-122, 3-124, 3-125, 3-129, 3-130, 3-131, 3-134, 3- 135, 3-136, 3-137, 3-138, 3-139, 3-140, 3-141, 3-142, 3-143, 3-144, 3-145, 3-146, 3-147, 3-148,3-149,3-150,3-153,4-004,4-007,4-009,5-001,6-001,7-001,7-002,7-003,7- 004,7-005,7-006,7-007,7-008,7-009,7-010,7-012,7-013,7-017,7-018,7-020,7-021, 7-022,8-001,8-002,8-003,8-004,9-003,14-001,14-002,14-003,14-007,14-008,14-009,14- 010,14-011,14-012,14-013,14-014,14-016,14-017,14-018,14-019,14-020,14-021,14-022,14-023, 14-024,14-025,14-028,14-030,14-032,14-033,14-034,14-035,14-036,14-037,14-038,14-039,14- 040,14-041,14-042,14-046,14-048,14-049.

Test Example 11 Control Effect Test on Sweet Potato Nematode Cellulose planted seedlings (approximately 2 weeks after germination) filled with 10 g of soil per cell were added 100 ppm of test chemical solution B of the compound of the present invention with distilled water. Dilute to concentration and treat 1 ml per strain. One hour after the treatment, water containing 2 L larvae of Meloidogyne incognita (2 L larvae: 100/1 ml) was inoculated to the strain, 1 ml per cell. It was kept in a greenhouse for 3 weeks, and the degree of root nodules formed at the root was determined according to the following disease index and disease severity, and the efficiency (%) for the untreated area was calculated by the following equation.

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

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

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

[Disease severity] = [Σ (attack index × number of diseased strains by index) / (4 × number of strains)] × 100
Efficacy (%) = [1- (treatment area incidence / no treatment area incidence)] × 100
As a result, among the tested compounds, the following compounds showed an efficiency (%) of 50% or more.
Compound of the present invention: No.1-002,1-003,1-004,1-006,1-007,1-009,1-013,1-014,1-015,1-016,1-017, 1-019,1-020,1-021,1-022,1-023,1-025,1-027,1-028,1-031,1-034,1-035,1-036,1- 038,1-044,1-045,1-046,1-047,1-049,1-050,1-051,1-052,1-056,1-058,1-060,1-062, 2-001,2-002,3-002,3-003,3-004,3-006,3-007,3-009,3-010,3-011,3-012,3-013,3- 014,3-016,3-017,3-020,3-021,3-024,3-025,3-026,3-027,3-028,3-029,3-031,3-036, 3-037,3-038,3-039,3-041,3-042,3-043,3-048,3-050,3-051,3-052,3-054,3-061,4- 001,4-003,6-001,7-001,7-002,7-003,7-004,7-006,7-008,7-010,7-012,8-001,8-002, 8-003,9-003,12-002,14-002,14-003,14-005,14-007,14-008,14-009,14-010,14-011,14-012,14- 013,14-014,14-016,14-017,14-018,14-019,14-020,14-022,14-024,14-030,14-032,14-035,14-036, 14-037, 14-038, 14-039, 14-046.

Test Example 12 Insecticidal test for torsion stomachworms After dispensing 60 μl of potato dextrose 1% agar medium to a 96-well plate, sterile water (10 eggs / 3 μl) containing eggs of torsion stomachworms (Haemonchus contortus), 30 μl was added per well. From this, test chemical solution B of the compound of the present invention was diluted with distilled water to a concentration of 10 ppm, added 10 μl per well, and allowed to stand at 25 ° C. under dark conditions. The number of unhatched eggs and the number of inactive larvae 4 days after the addition of the drug were measured, and the efficiency (%) for the untreated group was calculated from the same calculation formula as in Test Example 10.

As a result, among the tested compounds, the following compounds showed an efficiency (%) of 50% or more.
Compound of the present invention: No.1-001,1-002,1-003,1-004,1-005,1-006,1-007,1-008,1-009,1-010,1-012, 1-013,1-014,1-015,1-016,1-017,1-018,1-019,1-020,1-021,1-022,1-023,1-024,1- 025,1-026,1-027,1-028,1-029,1-030,1-031,1-032,1-033,1-034,1-035,1-036,1-037, 1-038,1-039,1-040,1-041,1-042,1-043,1-044,1-045,1-046,1-047,1-048,1-049,1- 050,1-051,1-052,1-053,1-054,1-055,1-056,1-057,1-058,1-059,1-060,1-061,1-062, 1-063,1-064,1-065,1-066,1-067,1-068,1-069,1-070,1-071,1-072,1-073,1-074,1- 075,1-076,1-077,1-078,1-079,1-080,1-081,1-083,1-084,1-085,1-086,1-087,1-088, 1-089,1-090,1-091,1-092,1-093,1-094,1-095,1-096,1-097,1-098,1-099,1-100,1- 101,1-102,1-103,1-106,1-107,1-108,1-109,1-110,1-111,1-112,1-113,1-114,1-115, 1-116,1-117,1-118,1-119,1-120,1-121,1-125,2-001,2-002,2-003,2-004,2-005,2- 006,2-007,2-008,2-009,2-010,2-011,2-012,2-013,2-014,2-015,2-016,2-017,2-018, 2-019,2-020,2-021,2-022,2-023,2-024,2-025,2-026,2-027,2-028,2-029,2-030,2- 031,2-032,2-033,2-034,2-035,2-036,2-037,2-038,2-039,2-040,2-041,2-044,2-045, 2-046,2-04 7,2-048,2-049,2-050,2-051,2-052,2-053,2-054,2-055,2-056,2-057,2-058,2-059, 2-060,2-061,2-062,2-063,2-064,2-065,2-066,3-001,3-002,3-003,3-004,3-005,3- 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, 3-019,3-020,3-021,3-022,3-023,3-024,3-025,3-026,3-027,3-029,3-030,3-031,3- 032,3-033,3-034,3-035,3-036,3-037,3-038,3-039,3-040,3-041,3-042,3-043,3-044, 3-045,3-046,3-047,3-048,3-049,3-050,3-051,3-052,3-053,3-054,3-055,3-056,3- 057,3-058,3-059,3-060,3-061,3-062,3-063,3-064,3-065,3-066,3-067,3-068,3-069, 3-070,3-071,3-072,3-073,3-074,3-075,3-076,3-077,3-078,3-079,3-083,3-084,3- 085,3-086,3-087,3-088,3-089,3-090,3-091,3-092,3-093,3-094,3-095,3-096,3-097, 3-098,3-099,3-100,3-101,3-102,3-103,3-104,3-105,3-106,3-107,3-108,3-109,3- 110, 3-111, 3-112, 3-113, 3-114, 3-115, 3-116, 3-117, 3-118, 3-119, 3-120, 3-121, 3-122, 3-123, 3-124, 3-125, 3-129, 3-130, 3-131, 3-132, 3-133, 3-134, 3-135, 3-136, 3-137, 3- 138, 3-139, 3-140, 3-141, 3-142, 3-143, 3-144, 3-145, 3-146, 3-147, 3-148, 3-149, 3-150, 3-151,3-152,3-153,4-001,4- 002,4-004,4-005,4-006,4-007,4-008,4-009,5-001,6-001,7-001,7-002,7-003,7-004, 7-005,7-006,7-007,7-008,7-009,7-010,7-011,7-012,7-013,7-014,7-015,7-016,7- 017,7-018,7-019,7-020,7-021,7-022,8-001,8-002,8-003,8-004,8-005,9-001,9-002, 9-003,9-005,9-006,9-007,9-009,9-010,11-001,12-003,14-001,14-002,14-003,14-004,14- 005,14-006,14-007,14-008,14-009,14-010,14-011,14-012,14-013,14-014,14-015,14-016,14-017, 14-018,14-019,14-020,14-021,14-022,14-023,14-024,14-025,14-026,14-027,14-028,14-030,14- 031,14-032,14-033,14-034,14-035,14-036,14-037,14-038,14-039,14-040,14-041,14-042,14-043, 14-044, 14-045, 14-046, 14-047, 14-048, 14-049, 14-050, 14-051, 14-052, 14-053, 15-001.

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

As a result, among the tested compounds, the following compounds showed an efficiency (%) of 50% or more.
Compound of the present invention: No.1-002,1-053,1-069,1-070,1-071,1-072,1-074,1-091,1-092,1-094,1-095, 1-096,1-097,1-098,1-099,1-100,1-101,1-102,1-103,1-106,1-107,1-108,1-109,1- 110,1-111,1-112,1-114,1-115,1-116,1-118,1-119,1-121,1-125,2-010,2-011,2-016, 2-021,2-022,2-023,2-025,2-027,2-028,2-029,2-030,2-031,2-032,2-033,2-034,2- 035,2-037,2-039,2-040,2-044,2-045,2-046,2-047,2-048,2-049,2-050,2-054,2-055, 2-056,2-057,2-058,2-059,2-060,2-061,2-062,2-063,2-064,2-065,2-066,2-067,3- 002,3-044,3-066,3-067,3-068,3-070,3-071,3-076,3-077,3-087,3-088,3-095,3-096, 3-098, 3-100, 3-101, 3-102, 3-104, 3-105, 3-106, 3-107, 3-110, 3-111, 3-112, 3-113, 3- 114, 3-116, 3-117, 3-118, 3-119, 3-120, 3-121, 3-122, 3-124, 3-129, 3-130, 3-131, 3-133, 3-134, 3-135, 3-136, 3-137, 3-138, 3-139, 3-140, 3-141, 3-142, 3-143, 3-144, 3-145, 3- 146,3-147,3-148,3-149,3-150,3-1151,3-152,3-153,4-007,4-008,4-009,7-018,7-019, 7-020,7-021,8-004,8-005,14-002,14-040.

Test Example 14 Insecticidal test against torsion stomachworm (comparison test)
After dispensing 60 μl of potato dextrose 1% agar medium to a 96-well plate, sterile water (10 eggs / 3 μl) containing eggs of Haemonchus contortus was added in an amount of 30 μl per well. From this, the test drug solution B of the compound of the present invention and the comparative compound was diluted to each predetermined concentration by adding distilled water, added 10 μl per well, and allowed to stand at 25 ° C. under dark conditions. The number of unhatched eggs and the number of inactive larvae 4 days after the addition of the drug were measured, and the efficiency (%) for the untreated group was calculated from the same calculation formula as in Test Example 10.

Tables 22 and 23 show the efficiency (%) of each test compound at each predetermined concentration.
Table 22 ――――――――――――――――――――――――――――――――
Concentration (ppm)
Test compound 10 3 0.3 0.1 0.03
――――――――――――――――――――――――――――――――
Compound of the present invention No.2-052 100 100 70 0 0
Comparative compound A 30 0 0 0 0
Compound of the present invention No.2-054 100 100 90 80 0
Comparative compound B 100 0 0 0 0
――――――――――――――――――――――――――――――――
Comparative compound A: WO2014-173921, compound X.8

  Comparative compound B: WO2014-173921, compound X.7

Table 23 ――――――――――――――――――――――――――――――――――――
Concentration (ppm)
Test compound 10 5 2.5 1.3 0.6 0.3
―――――――――――――――――――――――――――――――――――
Compound No. 9-005 100 90 100 100 100 0
Compound No. 9-006 100 90 100 100 90 0
Comparative compound C 100 80 0 0 0 0
―――――――――――――――――――――――――――――――――――
Comparative compound C: WO2015-125824, compound 8-027

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

Claims (21)

Formula (I):

Wherein, G ¹ represents a structure represented by G ¹ -1~G ¹ -16,

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 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, provided that when G ¹ represents a structure represented by G ¹ -10 and X ¹ represents dihalomethyl, X ² represents a hydrogen atom;
X ³ represents a hydrogen atom or C ₁ -C ₄ alkyl,
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 and Y ³ each independently represent a hydrogen atom, a halogen atom 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, (Z) _m Substituted phenyl (C ₁ -C ₄ ) alkoxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ haloalkylthio, C ₁ -C ₆ alkoxyamino, —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 with the carbon atoms to which R ¹ and R ² are attached, at which time the alkylene chain oxygen atom, it may contain one to two sulfur atom or nitrogen atom, and C ₁ -C ₄ alkyl group, C ₁ -C ₄ haloalkyl group, the oxo group or thioxo group may be optionally substituted Or R ¹ and R ² together form C ₁ -C ₆ alkylidene, C ₁ -C ₆ haloalkylidene or C ₁ -C ₄ alkoxy (C ₁ -C ₂ ) alkylidene. Represent,
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 to form a cyclopropyl ring with the carbon atom to which R ³ and R ⁴ are bonded,
R ⁵ is a hydrogen atom, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, (C ₁ -C ₂ ) alkyl substituted by R ⁸ , 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 9} or _C 1 -C ₄ alkoxycarbonyl Represent,
R ⁶ represents C ₃ -C ₆ cycloalkyl (C ₃ -C ₆ ) cycloalkyl, phenyl (C ₃ -C ₆ ) cycloalkyl, (Z) _m substituted phenyl or D-1 to D-29. Represent,
Further, R ¹ represents a fluorine atom, C ₁ -C ₆ alkyl or C ₁ -C ₆ alkoxy, R ² represents a fluorine atom or C ₁ -C ₆ alkyl, and R ³ represents C ₁ -C ₆ alkyl or C _When it represents _{1 to} C ₆ haloalkyl and R ⁴ represents a hydrogen atom or C _{1 to} C ₆ alkyl, R ⁶ represents a hydrogen atom, a halogen atom, C _{1 to} C ₆ alkyl, C _{1 to} C ₆ haloalkyl, (C ₁ -C ₄ ) alkyl, C ₃ -C ₁₀ cycloalkyl, C ₃ -C ₁₀ halocycloalkyl, hydroxy (C ₃ -C ₆ ) cycloalkyl, C ₁ -C ₄ optionally substituted by R ¹⁰ Alkoxy (C ₃ -C ₆ ) cycloalkyl, C ₄ -C ₁₀ cycloalkenyl, C ₄ -C ₁₀ halocycloalkenyl, tri (C ₁ -C ₄ alkyl) silyl, phenyldimethylsilyl, -C (R ¹¹ ) = May represent NOR ¹² or phenyl;
D-1 to D-29 each represent an aromatic heterocycle 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 or n represents 2 or more, representing Kirthio, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ haloalkylsulfonyl, di (C ₁ -C ₄ alkyl) amino, phenyl or D-30-D-36 Each Z may be the same as or different from each other, and when two Zs are adjacent to each other, the two adjacent Zs are —CH ₂ CH ₂ CH ₂ —, — CH ₂ CH ₂ O—, —CH ₂ OCH ₂ —, —OCH ₂ O—, —CH ₂ CH ₂ S—, —CH ₂ SCH 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-, -OCH ₂ CH ₂ S-, -SCH ₂ CH ₂ S-, -OCH = CH-, -SCH = CH-, -N (R ¹³ ) CH = CH-, -OCH = N-, -SCH = N-, -N (R ¹³ ) CH = N-,- By forming N (R ¹³ ) N = CH-, -CH = CH-CH = CH-, -N = CHCH = CH-, -N = CHCH = N- or -N = CHN = CH-, respectively. Forms a 5- or 6-membered ring with the carbon atom to which Z At best, this time, the hydrogen atoms bonded to each carbon atom forming the ring may be optionally substituted by halogen atom or C ₁ -C ₄ alkyl group,
D-30 to D-36 each represent an aromatic heterocycle represented by the following structural formula,

Z ^a represents a halogen atom, cyano, methyl, difluoromethyl or trifluoromethyl, and when n represents 2 or more, each Z ^a may be the same as or different from each other;
R ⁷ represents C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl,
R ⁸ represents cyano, —OR ¹⁴ , C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkoxycarbonyl, —C (O) NH ₂ or —C (S) NH ₂ ;
R ⁹ represents C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxymethyl, C ₃ -C ₄ cycloalkyl or C ₂ -C ₄ alkenyl,
R ¹⁰ represents cyano, —OR ¹⁵ , —S (O) _r R ¹⁶ or —N (R ¹⁸ ) R ¹⁷ ,
R ¹¹ represents a hydrogen atom or C ₁ -C ₄ alkyl;
R ¹² represents C ₁ -C ₄ alkyl;
R ¹³ represents C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl,
R ¹⁴ 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 ¹⁵ 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 ¹⁶ 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 ¹⁷ and R ¹⁸ 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, C ₃ -C ₄ alkynyl, or represents phenyl which is substituted by phenyl or (Z) _m,
Alternatively, R ¹⁷ and R ¹⁸ may form a C _{2 to} C ₅ alkylene chain together to form a 3 to 6 membered ring with the nitrogen atom to which R ¹⁷ and R ¹⁸ are bonded. represents, at this time the alkylene chain may contain one oxygen atom or sulfur atom, and C ₁ -C ₄ alkyl group, C ₁ -C ₄ haloalkyl groups, also optionally substituted by oxo group or thioxo group Often,
R ¹⁹ represents C ₁ -C ₄ alkyl, and when p represents 2, each R ¹⁹ 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. ]
An alkynylpyridine-substituted amide compound represented by the formula: N-oxide or salt thereof. G ^{1 is, G 1 -1, G 1 -2} , G 1 -3, G 1 -4, G 1 -5, G 1 -6, G 1 -7, G 1 -8, G 1 -9, G ¹ -10, G ¹ -11, G ¹ -12, G ¹ -14 or G ¹ -16 represents a structure represented,
X ¹ represents a halogen atom, nitro, methyl, difluoromethyl, trifluoromethyl, methoxy, methylthio, methylsulfonyl, difluoromethylsulfonyl or trifluoromethylsulfonyl,
X ² represents a hydrogen atom, a fluorine atom or a chlorine atom, provided that when G ¹ represents a structure represented by G ¹ -10 and X ¹ represents difluoromethyl, X ² represents a hydrogen atom. Represent,
X ³ represents methyl,
Y ¹ represents a halogen atom or methyl;
Y ² represents a hydrogen atom or methyl,
Y ³ represents a hydrogen atom,
R ¹ is hydrogen atom, fluorine atom, C ₁ -C ₃ alkyl, C ₁ -C ₃ haloalkyl, benzyl, phenylmethyl substituted by (Z) _m , cyclopropyl, C ₁ -C ₃ alkoxy, C _1- C ₃ haloalkoxy, C ₃ -C ₄ alkenyloxy, C ₃ -C ₄ alkynyloxy, cyanomethoxy, benzyloxy, phenylmethoxy substituted by (Z) _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, which indicates that R ¹ and R ² form a cyclopropyl ring with the carbon atom to which R ¹ and R ² are bonded, or R ¹ and R ² are Together represents C ₁ -C ₂ alkylidene or C ₁ -C ₂ haloalkylidene;
R ³ represents a hydrogen atom, methyl, ethyl or fluoromethyl,
R ⁴ represents a hydrogen atom or methyl,
Alternatively, R ³ and R ⁴ together form an ethylene chain to form a cyclopropyl ring with the carbon atom to which R ³ and R ⁴ are bonded,
R ⁵ represents a hydrogen atom, cyclopropyl or methoxy,
R ⁶ represents phenyl, D-1, D-2, D-6, D-8, D-23, D-24, D-25 or D-26 substituted by (Z) _m ;
Further, when R ¹ represents a fluorine atom or C ₁ -C ₃ alkyl, R ² represents a fluorine atom or methyl, R ³ represents methyl or ethyl, and R ⁴ represents a hydrogen atom or methyl, R ⁶ is a hydrogen atom, a halogen atom, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, (C ₁ -C ₄ ) alkyl optionally substituted by R ¹⁰ , C ₃ -C ₆ cycloalkyl, C _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) May represent silyl, -C (R ¹¹ ) = NOR ¹² or phenyl;
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-33 or D- 35, when m or n represents 2 or more, each Z may be the same as or different from each other. Further, when two Zs are adjacent to each other, two Zs are adjacent to each other. Each Z forms —OCH ₂ O—, —OCH ₂ CH ₂ O— or —CH═CH—CH═CH— to form a 5- or 6-membered ring with the carbon atom to which each Z is attached. In this case, the hydrogen atom bonded to each carbon atom forming the ring is a halogen atom. Or it may be optionally substituted by a methyl group,
Z ^a represents a halogen atom, methyl or trifluoromethyl,
R ⁷ represents methyl or ethyl,
R ¹⁰ represents —OR ¹⁵ or —S (O) _r R ¹⁶ ;
R ¹¹ represents a hydrogen atom or methyl,
R ¹² represents methyl or ethyl,
R ¹⁵ represents a hydrogen atom, methyl, ethyl or C ₁ -C ₂ haloalkyl,
R ¹⁶ represents methyl, ethyl or C ₁ -C ₂ haloalkyl,
2. Alkynylpyridine substituted amide compounds according to claim 1, their N-oxides or salts. G ^{1 is, G 1 -1, G 1 -2} , G 1 -3, G 1 -4, G 1 -5, G 1 -6, G 1 -7, G 1 -8, G 1 -10, G ¹ -11, G ¹ -12, G ¹ -14 or G ¹ -16 represents a structure represented,
X ¹ represents a halogen atom, nitro, methyl, difluoromethyl, trifluoromethyl, methoxy, methylthio, methylsulfonyl or difluoromethylsulfonyl,
X ² represents a hydrogen atom or a fluorine atom, provided that when G ¹ represents a structure represented by G ¹ -10 and X ¹ represents difluoromethyl, X ² represents a hydrogen atom;
Y ¹ represents a halogen atom,
Y ² represents a hydrogen atom,
R ¹ represents a hydrogen atom, a fluorine atom, methyl or methoxy,
R ² represents a hydrogen atom, a fluorine atom or methyl,
Alternatively, R ¹ and R ² together form an ethylene chain, thereby forming a cyclopropyl ring with the carbon atom to which R ¹ and R ² are bonded,
R ³ represents a hydrogen atom or methyl,
R ⁴ represents a hydrogen atom or methyl,
R ⁵ represents a hydrogen atom or cyclopropyl,
R ⁶ represents (Z) _m substituted phenyl, D-1, D-2, D-6, D-8, D-23 or D-25;
Further, when R ¹ represents a fluorine atom, R ² represents a fluorine atom, R ³ represents methyl, and R ⁴ represents a hydrogen atom or methyl, R ⁶ represents C ₁ -C ₄ haloalkyl or C ₃ -C ₆ cycloalkyl may represent,
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, represents C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ haloalkylthio, C ₁ -C ₄ haloalkylsulfinyl or _C 1 -C ₄ haloalkylsulfonyl, when m or n is 2 or more, Each Z may be the same as or different from each other. Further, when two Zs are adjacent to each other, the two adjacent Zs are —OCH ₂ O— or —CH═CH—CH═. By forming CH-, a 5-membered ring or a 6-membered ring may be formed together with the carbon atom to which each Z is bonded. At this time, the hydrogen atom bonded to each carbon atom forming the ring is a halogen atom. Optionally substituted by
R ⁷ represents methyl,
R ¹³ represents C ₁ -C ₄ alkyl;
m represents 1, 2 or 3;
n represents 0, 1 or 2;
The alkynylpyridine-substituted amide compound according to claim 2. G ¹ represents the structure represented by G ¹ -1,
X ¹ represents a halogen atom, methyl or trifluoromethyl,
X ² represents a hydrogen atom or a fluorine atom,
4. Alkynylpyridine substituted amide compounds according to claims 1 to 3, their N-oxides or salts. G ¹ represents a structure represented by G ¹ -2 or G ¹ -3,
X ¹ represents a halogen atom, methyl, difluoromethyl, trifluoromethyl, methylthio, methylsulfonyl or difluoromethylsulfonyl,
4. Alkynylpyridine substituted amide compounds according to claims 1 to 3, their N-oxides or salts. G ¹ represents the structure represented by G ¹ -4,
X ¹ represents a halogen atom or trifluoromethyl,
4. Alkynylpyridine substituted amide compounds according to claims 1 to 3, their N-oxides or salts. G ¹ represents a structure represented by G ¹ -7 or G ¹ -8,
X ¹ represents a halogen atom, methyl or trifluoromethyl,
4. Alkynylpyridine substituted amide compounds according to claims 1 to 3, their N-oxides or salts. G ¹ represents a structure represented by G ¹ -10;
X ¹ represents difluoromethyl or trifluoromethyl,
X ² represents a hydrogen atom,
R ⁷ represents methyl,
4. Alkynylpyridine substituted amide compounds according to claims 1 to 3, their N-oxides or salts. R ⁶ represents (Z) _m substituted phenyl, D-1, D-2, D-6, D-8, D-23 or D-25;
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, represents C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ haloalkylthio, C ₁ -C ₄ haloalkylsulfinyl or _C 1 -C ₄ haloalkylsulfonyl, when m or n is 2 or more, Each Z may be the same as or different from each other. Further, when two Zs are adjacent to each other, the two adjacent Zs are —OCH ₂ O— or —CH═CH—CH═. By forming CH-, a 5-membered ring or a 6-membered ring may be formed together with the carbon atom to which each Z is bonded. At this time, the hydrogen atom bonded to each carbon atom forming the ring is a halogen atom. Optionally substituted by
R ¹³ represents C ₁ -C ₄ alkyl;
m represents 1, 2 or 3;
n represents 0, 1 or 2;
The alkynylpyridine substituted amide compounds according to claim 1 to 8, their N-oxides or salts. R ¹ represents a fluorine atom,
R ² represents a fluorine atom,
R ³ represents methyl,
R ⁴ represents a hydrogen atom,
R ⁶ represents C ₁ -C ₄ haloalkyl or C ₃ -C ₆ cycloalkyl,
The alkynylpyridine substituted amide compounds according to claim 1 to 8, their N-oxides or salts. Formula (II):

[Wherein Y ¹ represents a halogen atom,
Y ² represents a hydrogen atom,
Y ³ represents a hydrogen atom,
R ¹ represents a hydrogen atom, a fluorine atom, methyl or methoxy,
R ² represents a hydrogen atom, a fluorine atom or methyl,
Alternatively, R ¹ and R ² together form an ethylene chain, thereby forming a cyclopropyl ring with the carbon atom to which R ¹ and R ² are bonded,
R ³ represents a hydrogen atom or methyl,
R ⁴ represents a hydrogen atom or methyl,
R ⁵ represents a hydrogen atom or cyclopropyl,
R ⁶ represents (Z) _m substituted phenyl, D-1, D-2, D-6, D-8, D-23 or D-25;
Further, when R ¹ represents a fluorine atom, R ² represents a fluorine atom, R ³ represents methyl, and R ⁴ represents a hydrogen atom or methyl, R ⁶ represents a C ₁ -C ₄ haloalkyl, C ₃ -C ₆ cycloalkyl or tri _(C 1 -C ₄ alkyl) may be a silyl,
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, represents C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ haloalkylthio, C ₁ -C ₄ haloalkylsulfinyl or _C 1 -C ₄ haloalkylsulfonyl, when m or n is 2 or more, Each Z may be the same as or different from each other. Further, when two Zs are adjacent to each other, the two adjacent Zs are —OCH ₂ O— or —CH═CH—CH═. By forming CH-, a 5-membered ring or a 6-membered ring may be formed together with the carbon atom to which each Z is bonded. At this time, the hydrogen atom bonded to each carbon atom forming the ring is a halogen atom. Optionally substituted by
R ¹³ represents C ₁ -C ₄ alkyl;
m represents 1, 2 or 3;
n represents 0, 1 or 2. ]
The manufacturing intermediate of the alkynyl pyridine substituted amide compound of Claims 1-10 represented by these.   A pesticidal composition containing one or more selected from the alkynylpyridine-substituted amide compounds or salts thereof according to claim 1 as an active ingredient.   The antifungal agent or parasite control agent composition of mammals or birds which contains as an active ingredient 1 or more types chosen from the alkynyl pyridine substituted amide compound or its salt of Claims 1-10.   The endoparasite control composition according to claim 13, for oral administration to mammals or birds.   The endoparasite control composition according to claim 13, for parenteral administration to mammals or birds.   16. The endoparasite control composition according to claim 15, wherein the parenteral administration method to mammals or birds is administration by injection.   The endoparasite control composition according to claim 15, wherein the parenteral administration to mammals or birds is transdermal administration.   An agricultural and horticultural fungicide or nematicide composition comprising, as an active ingredient, one or more selected from the alkynylpyridine-substituted amide compounds or salts thereof according to claim 1.   The agricultural or horticultural fungicide or nematicide composition according to claim 18 for spraying foliage on plants.   The agricultural or horticultural fungicide or nematicide composition according to claim 18 for treating soil on which plants grow.   The agricultural or horticultural fungicide or nematicide composition according to claim 18 for treating plant seeds, tuberous roots and rhizomes.