JP2013256468A - Parasite controlling agent for animal - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a new controlling agent for harmful arthropods and Nematoda parasitic to mammals, birds or the like.SOLUTION: A parasite controlling agent for animals is a composition including one or more kinds selected from a pyrazole derivative represented by general formula (1) or its salt as an active ingredients [wherein, B denotes a pyrazole ring represented by structural formula shown in formula B; Adenotes -N(-O)or -CR; Adenotes phenyl substituted with a heterocyclic ring, (Z1)or the like; R, R, Rdenote a hydrogen atom, a halogen atom Cto Calkyl or the like; and Zdenotes a halogen atom, Cto Calkyl, (Cto C) alkyl optionally substituted with Ror the like, respectively].

Description

  The present invention relates to a harmful external or endoparasite control agent that parasitizes companion animals, pet animals, mammals as domestic animals and poultry, birds, and the like.

  Patent Documents 1 to 17 and Non-Patent Documents 1 and 2 disclose certain types of pyrazole derivatives, but do not specifically disclose the animal parasite control agents according to the present invention.

International Publication No. 2011/045224 International Publication No. 2010/006713 International Publication No. 2008/046527 International Publication No. 2008/016131 International Publication No. 2007/027842 International Publication No. 2006/107771 International Publication No. 2006/044502 International Publication No. 2005/121099 International Publication No. 2004/072033 International Publication No. 2004/029043 International Publication No. 2008/011131 International Publication No. 2003/051833 US Patent Application Publication No. 2003/144309 International Publication No. 2002/092573 European Patent Application No. 1104760 U.S. Pat. No. 3,254,093 JP 2010-006717 A

Tetrahedron Letter 2002, 43, 2171 Journal of Medicinal Chemistry 2008, 51, 2267

  For the purpose of maintaining the health of target mammals, birds, etc., the extermination of external or internal parasites parasitic on companion animals, pet animals, livestock and poultry mammals, birds, etc. When birds are livestock and poultry, it is an important issue for the purpose of stable production of safe food and high-quality living materials such as wool and feathers. From such a viewpoint, conventionally, development of a parasite control agent aimed at controlling harmful external or internal parasites has progressed, and effective drugs have been put to practical use until now.

  However, due to the long-term use of such drugs, in recent years, parasites have acquired drug resistance, and the number of scenes in which it has become difficult to control them with conventionally used drugs has increased. Under such circumstances, development of a novel parasite control agent and an effective control method not only having high parasite control activity but also low toxicity and low persistence is always expected.

  As a result of intensive studies aimed at solving the above problems, the present inventors have found that an active ingredient comprising a pyrazole derivative represented by the following general formula (1) and a salt thereof, or a mixture of two or more selected from them. And one or more components selected from a surfactant, a solid carrier and a liquid carrier, and if necessary, one or more additional components of an effective amount of a known parasite control agent. It was found that an effective amount of the composition was orally or parenterally administered to mammals, birds, etc., and showed excellent parasite control activity, and the present invention was completed.

  That is, the present invention relates to the following [1] to [19].

[1]
General formula (1):

[In the formula, B represents a pyrazole ring represented by the following structural formula;

A ¹ represents —N (—O) _{m 2} or —CR ¹ ,
A ^{2 is,} D1-1~D1-105, represents naphthyl substituted with ^{the (Z} ₁₎ phenyl substituted with _q or ^(Z _{1) q,}
R ¹ is a hydrogen atom, a halogen atom, cyano, nitro, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, C ₁ -C ₆ alkylthio, C ₁ -C _{6 alkylsulfinyl,} C 1 -C ₆ represent _{alkylsulfonyl,} C 1 -C _{6 haloalkylthio,} a C 1 -C ₆ haloalkylsulfinyl or _C 1 -C ₆ haloalkylsulfonyl,
R ² is a halogen atom, cyano, nitro, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, C ₁ -C ₆ alkylthio, C _1- C _{6 alkylsulfinyl,} C 1 -C _{6 alkylsulfonyl,} C 1 -C _{6 haloalkylthio,} represents C 1 -C ₆ haloalkylsulfinyl or _C 1 -C ₆ haloalkylsulfonyl, when n1 represents an integer of 2 or more, each R ² may be the same as or different from each other.
R ³ and R ⁴ are each independently a hydrogen atom, a halogen atom, C ₁ -C ₆ alkyl, C ₃ -C ₆ cycloalkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ alkylsulfonyl, C ₁ -C ₆ haloalkylthio, C ₁ -C _{6 haloalkylsulfinyl,} C 1 -C ₆ haloalkylsulfonyl, _cyano, C 1 -C _{6 alkoxycarbonyl,} C 1 -C _{6 alkylcarbonyl,} C 1 -C ₆ alkylaminocarbonyl or di _(C 1 -C ₆ alkyl ) Represents aminocarbonyl,
However, when ^{A 2} is a D1-57, ^{R 3} _is, C 1 -C _{6 alkoxy,} C 1 -C _{6 haloalkoxy,} C 1 -C _{6 alkylthio,} C 1 -C _{6 alkylsulfinyl,} C 1 -C ₆ alkyl except _sulfonyl, C 1 -C _{6 haloalkylthio,} C 1 -C _{6 haloalkylsulfinyl,} a C 1 -C ₆ haloalkylsulfonyl,
D1-1 to D1-105 each represent a ring represented by the following structural formula;

X ¹ is a halogen atom, cyano, nitro, azide, —SCN, —SF ₅ , C ₁ -C ₁₂ alkyl, (C ₁ -C ₁₂ ) alkyl optionally substituted with R ⁵ , C ₃ -C ₁₂ cyclo. alkyl, optionally substituted with ^{R 5} _(C 3 ~C _{12) cycloalkyl,} C 2 _{-C 12} alkenyl, optionally substituted with ^{R 5} _(C 2 ~C _{12) alkenyl,} C 3 _{-C 12} cycloalkyl alkenyl, optionally substituted with ^{R 5} _(C 3 ~C _{12) cycloalkenyl,} C 2 _{-C 12} alkynyl, optionally substituted with ^{R 5} _(C 2 ~C _{12) alkynyl,} C 3 _{-C 12} allenyl _{^{, -OH, -OR 6, -SH,}} -S (O) r R 6, -S (= NR 8b) R 6a, -S (O) (= NR 8b) R 6a, -N (R 8a) R ^{8, -C (O) R 7} , -C (O) ^{H, -C (O) OR 6a} , -C (O) SR 6a, -C (S) OR 6a, -C (S) SR 6a, -C (O) N (R 8a) R 8, -C ( ^{S) N (R 8a) R} 8, -C (O) N (R 8a) N (R 8a) R 8, -C (O) N (R 8a) OR 6, -C (O) C (O) OR ^6a , -C (R ⁷ ) = NOH, -C (R ⁷ ) = NOR ⁶ , -C (R ⁷ ) = NN (R ^8a ) R ⁸ , -C (= NOR ⁶ ) N (R ^8a ) R ^{8, -C (= NR 8b)} OR 6a, -C (= NR 8b) SR 6a, -C (= NR 8b) N (R 8a) R 8, -S (O) 2 OR 6, -S (O ) ₂ N (R ^8a ) R ⁸ , -ON (R ^8a ) R ⁸ , -N (R ^8a ) OR ⁶ , -Si (R ^9a ) (R ^9b ) R ⁹ , -P (O) (OR ¹⁰ ) _2, -P (S ^(OR ₁₀₎ 2, -P _(phenyl) 2, -P (O) _{(phenyl) 2,} phenyl, ^naphthyl, (Z ₂₎ phenyl substituted with ^_q2, (Z ₂₎ is substituted with _q2 naphthyl or D2 -1 to D2-102, and when p1, p2, p4, p5, p6 or p8 represents an integer of 2 or more, each X ¹ may be the same as or different from each other; When two X ¹ are adjacent to each other, the two adjacent X ¹ 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 -, - CH 2 CH 2 CH 2 CH 2 -, - CH 2 CH 2 CH 2 O -, - CH 2 CH 2 OCH 2 -, - CH 2 OCH 2 O _{-, - OCH 2 CH 2 O} -, - CH 2 C By forming H ₂ CH ₂ S— or —OCH ₂ CH ₂ S—, a 5-membered ring or a 6-membered ring may be formed together with the carbon atom to which each X ¹ is bonded. The hydrogen atom bonded to each carbon atom may be optionally replaced by X ² ;
Alternatively, ^{A 2} is D1-1, D1-2, D1-5~D1-17, D1-19, D1-20, D1-22~D1-26, D1-28, D1-29, D1-36~D1 -40, D1-42, D1-43, D1-46, D1-48, D1-52 to D1-57, D1-59 to D1-63, D1-67 to D1-70, D1-74, D1-80 -D1-87, D1-94-D1-96, D1-98, D1-99 or D1-103-D1-105, and p1, p2, p3, p4, p5, p6 or p8 is an integer of 1 or more In the case where the carbon atom bonded to X ¹ and the carbon atom bonded to the 4-position of pyrazole represented by formula (B) are adjacent to each other, X ¹ together with R ³ is C ₂ -C _4. by forming the alkylene chain or _C 2 -C ₄ alkenylene chain, ^{X 1} Bind may form a 6-8 membered ring with the carbon atom bonded carbon atoms and A ² binding carbon atoms and R ^3, alkylene chain or alkenylene chain this time, an oxygen atom, a sulfur atom or a nitrogen atom It may include, and halogen atom, a cyano group, a nitro _group, C 1 -C ₆ alkyl _group, C 1 -C ₆ haloalkyl _group, C 1 -C ₆ alkoxy _group, C 1 -C ₆ haloalkoxy group, _{C 1} -C ₆ alkylthio _group, C 1 -C ₆ haloalkylthio group, -NH _{2 group,} C 1 -C ₆ alkylamino group, di _(C 1 ~C ₆₎ alkylamino group, phenyl, ^naphthyl, (Z _{2) q2} Phenyl substituted by (Z ² ) _q2 substituted by naphthyl or D2-1 to D2-102, oxo group, thioxo group, imino group, C ₁ -C ₆ alkylimino group or C ₁ -C ₆ may be optionally substituted by an alkoxyimino group, or A ² may be D1-1, D1-2, D1-5 to D1-17, D1-19, D1-20, D1-22 to D1-26, D1-28, D1-29, D1-36 to D1-40, D1-42, D1-43, D1-46, D1-48, D1-52 to D1-57, D1-59 to D1-63, D1- 67~D1-70, D1-74, D1-80~D1-87, D1-94~D1-96, D1-98, represents D1-99 or D1-103~D1-105, ^{R 3} represents a methylene At this time, R ³ may form a 5-membered ring together with the carbon atom to which R ³ is bonded, the carbon atom to which A ² is bonded, and the ^two carbon atoms that form A ² , where R ³ is a halogen atom , cyano group, nitro _group, C 1 -C ₆ alkyl group, ₁ -C ₆ haloalkyl _group, C 1 -C ₆ alkoxy _group, C 1 -C ₆ haloalkoxy _group, C 1 -C ₆ alkylthio _group, C 1 -C ₆ haloalkylthio group, -NH _{2 group,} C 1 -C ₆ alkylamino group, di (C ₁ -C ₆ ) alkylamino group, oxo group, thioxo group, imino group, C ₁ -C ₆ alkylimino group or C ₁ -C ₆ alkoxyimino group Often,
X ^1a is a hydrogen atom, a halogen atom, cyano, nitro, azide, —SCN, —SF ₅ , C _{1 to} C ₁₂ alkyl, (C _{1 to} C ₁₂ ) alkyl optionally substituted with R ^5a , C ₃ to C ₁₂ ^cycloalkyl, optionally substituted with ^{R 5a} _(C 3 ~C _{12) cycloalkyl,} substituted C 2 _{-C 12} ^alkenyl, optionally with ^{R 5a} _(C 2 ~C _{12) alkenyl, C} 3 ~ C ₁₂ ^{cycloalkenyl,} optionally substituted with ^{R 5a} _(C 3 ~C _{12) cycloalkenyl,} C 2 _{-C 12} ^alkynyl, optionally substituted with ^{R 5a} _(C 2 ~C _{12) alkynyl, C} 3 ~ C _{12 ^{allenyl, -OH, -OR 6, -S (}} O) r R 6, -S (= NR 8b) R 6a, -S (O) (= NR 8b) R 6a, -N (R 8a) R ^8, -C (O) R ^{, -C (O) OR 6a,} -C (O) SR 6a, -C (S) OR 6a, -C (S) SR 6a, -C (O) N (R 8a) R 8, -C (S ) N (R ^8a ) R ⁸ , —C (O) N (R ^8a ) N (R ^8a ) R ⁸ , —C (O) N (R ^8a ) OR ⁶ , —C (O) C (O) OR ^{6a, -C (R 7) =} NOH, -C (R 7) = NOR 6, -C (R 7) = NN (R 8a) R 8, -C (= NOR 6) N (R 8a) R 8 ^{, -C (= NR 8b) OR} 6a, -C (= NR 8b) SR 6a, -C (= NR 8b) N (R 8a) R 8, -S (O) 2 N (R 8a) R 8, ^{-Si (R 9a) (R 9b} ) R 9, -P (O) (OR 10) 2, -P (S) (OR 10) 2, -P ( _phenyl) 2, -P _(O) (phenyl) _2, Fe Le, ^naphthyl, (Z ₂₎ phenyl substituted with ^_q2, represents a (Z ₂₎ naphthyl or D2-1~D2-102 substituted with _q2, ^{further, if X 1} is present at the adjacent position to ^{X 1a} the, ^{X 1a} and ^{X 1} _{adjacent, -CH 2 CH 2 O -,} - CH 2 CH 2 CH 2 CH 2 -, - CH = CHCH = CH -, - N = CHCH = CH -, - CH = By forming N—CH═CH—, —CH═CH—N═CH— or —CH═CH—CH═N—, a 5- or 6-membered ring with the atoms to which each of X ^1a and X ¹ is bonded is formed. In this case, the hydrogen atom bonded to each carbon atom forming the ring may be optionally substituted by a halogen atom, a C ₁ -C ₆ alkyl group or a C ₁ -C ₆ haloalkyl group. or, ^{a 2} is D1-6, D1-15 D1-25, D1-27, D1-40, D1-44, D1-47, D1-50, D1-73, when representing the D1-86 or ^D1-93, the ^{X 1a} taken together with ^{R 3} C By forming a _{2 to} C ₄ alkylene chain or a C _{2 to} C ₄ alkenylene chain, a 6 to 8 membered ring is formed together with the nitrogen atom to which X ^1a is bonded, the carbon atom to which R ³ is bonded, and the carbon atom to which A ² is bonded. In this case, the alkylene chain or alkenylene chain may contain 1 to 3 oxygen atoms, sulfur atoms or nitrogen atoms, and is a halogen atom, cyano group, nitro group, C ₁ -C ₆ alkyl group, C ₁ -C ₆ haloalkyl _group, C 1 -C ₆ alkoxy _group, C 1 -C ₆ haloalkoxy _group, C 1 -C ₆ alkylthio _group, C 1 -C ₆ haloalkylthio group, -NH _{2 group, C} 1 ~ C ₆ Archi Optionally substituted by a ruamino group, a di (C ₁ -C ₆ ) alkylamino group, an oxo group, a thioxo group, an imino group, a C ₁ -C ₆ alkylimino group or a C ₁ -C ₆ alkoxyimino group,
D2-1 to D2-102 each represent a ring represented by the following structural formula;

Z ¹ Is a halogen atom, cyano, nitro, azide, -SCN, -SF ₅ , C ₁ ~ C ₁₂ Alkyl, R ⁵ Optionally substituted with (C ₁ ~ C ₁₂ ) Alkyl, C ₃ ~ C ₁₂ Cycloalkyl, R ⁵ Optionally substituted with (C ₃ ~ C ₁₂ ) Cycloalkyl, C ₂ ~ C ₁₂ Alkenyl, R ⁵ Optionally substituted with (C ₂ ~ C ₁₂ ) Alkenyl, C ₃ ~ C ₁₂ Cycloalkenyl, R ⁵ Optionally substituted with (C ₃ ~ C ₁₂ ) Cycloalkenyl, C ₂ ~ C ₁₂ Alkynyl, R ⁵ Optionally substituted with (C ₂ ~ C ₁₂ ) Alkynyl, C ₃ ~ C ₁₂ Allenyl, -OH, -OR ⁶ , -SH, -S (O) _r R ⁶ , -S (= NR ^8b ) R ^6a , -S (O) (= NR ^8b ) R ^6a , -N (R ^8a ) R ⁸ , -C (O) R ⁷ , -C (O) OR ^6a , -C (O) SR ^6a , -C (S) OR ^6a , -C (S) SR ^6a , -C (O) N (R ^8a ) R ⁸ , -C (S) N (R ^8a ) R ⁸ , -C (O) N (R ^8a ) N (R ^8a ) R ⁸ , -C (O) N (R ^8a ) OR ⁶ , -C (O) C (O) OR ^6a , -C (R ⁷ ) = NOH, -C (R ⁷ ) = NOR ⁶ , -C (R ⁷ ) = NN (R ^8a ) R ⁸ , -C (= NOR ^6a ) N (R ^8a ) R ⁸ , -C (= NR ^8b ) OR ^6a , -C (= NR ^8b SR ^6a , -C (= NR ^8b ) N (R ^8a ) R ⁸ , -S (O) ₂ OR ^6a , -S (O) ₂ N (R ^8a ) R ⁸ , -ON (R ^8a ) R ⁸ , -N (R ^8a ) OR ⁶ , -Si (R ^9a ) (R ^9b ) R ⁹ , -P (O) (OR ¹⁰ ) ₂ , -P (S) (OR ¹⁰ ) ₂ , -P (phenyl) ₂ , P (O) (phenyl) ₂ , Phenyl, naphthyl, (Z ² ) _q2 Phenyl substituted with (Z ² ) _q2 Represents naphthyl substituted with D2-1 to D2-102, and when q represents an integer of 2 or more, each Z ¹ May be the same or different from each other, and two Z ¹ Are adjacent to each other, two adjacent Z ¹ Is -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 -, -CH ₂ CH ₂ N (X ^1a )-, -CH ₂ N (X ^1a ) CH ₂ -, -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-, -CH ₂ CH = CH-, -OCH = CH-, -SCH = CH-, -N (X ^1a ) CH = CH-, -OCH = N-, -SCH = N-, -N (X ^1a ) CH = N-, -N (X ^1a ) N = CH-, -OCH ₂ CH = CH-, -N = CHCH = CH-, -CH = NCH = CH-, -N = NCH = CH-, -CH = NN = CH-, -N = CHCH = N- or -N = CHN = By forming CH-, each Z ¹ May form a 5-membered ring or a 6-membered ring together with the carbon atom to which is bonded, and in this case, the hydrogen atom bonded to each carbon atom forming the ring is Z ² Or when q represents an integer of 1 or more, Z ¹ When the carbon atom bonded to the carbon atom bonded to the 4-position of pyrazole in formula (B) is adjacent, Z ¹ Is R ³ Together with C ₂ ~ C ₄ Alkylene chain or C ₂ ~ C ₄ By forming an alkenylene chain, Z ¹ Carbon atoms to which R ³ Carbon atoms to which ² A 6 to 8 membered ring may be formed together with the carbon atom to which the alkylene group is bonded. In this case, the alkylene chain or alkenylene chain may contain an oxygen atom, a sulfur atom or a nitrogen atom, and a halogen atom, a cyano group, a nitro group, C ₁ ~ C ₆ Alkyl group, C ₁ ~ C ₆ Haloalkyl group, C ₁ ~ C ₆ Alkoxy group, C ₁ ~ C ₆ Haloalkoxy group, C ₁ ~ C ₆ Alkylthio group, C ₁ ~ C ₆ Haloalkylthio group, -NH ₂ Group, C ₁ ~ C ₆ Alkylamino group, di (C ₁ ~ C ₆ ) Alkylamino group, oxo group, thioxo group, imino group, C ₁ ~ C ₆ An alkylimino group or C ₁ ~ C ₆ Optionally substituted by an alkoxyimino group,
R ⁵ And R ^5a Each independently represents a halogen atom, cyano, nitro, C ₃ ~ C ₈ Cycloalkyl, R ¹⁴ Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkyl, C ₃ ~ C ₈ Cycloalkenyl, R ¹⁴ Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkenyl, -OH, -OR ¹¹ , -SH, -S (O) _r R ¹¹ , -S (= NR ^13b ) R ^11a , -S (O) (= NR ^13b ) R ^11a , -N (R ^13a ) R ¹³ , -C (O) R ¹² , -C (O) OH, -C (O) OR ^11a , -C (O) SR ^11a , -C (S) OR ^11a , -C (S) SR ^11a , -C (O) N (R ^13a ) R ¹³ , -C (S) N (R ^13a ) R ¹³ , -C (O) N (R ^13a ) N (R ^13a ) R ¹³ , -C (O) N (R ^13a ) OR ¹¹ , -C (R ¹² ) = NOH, -C (R ¹² ) = NOR ¹¹ , -C (R ¹² ) = NN (R ^13a ) R ¹³ , -C (= NOR ^11a ) N (R ^13a ) R ¹³ , -C (= NR ^13b ) OR ^11a , -C (= NR ^13b SR ^11a , -C (= NR ^13b ) N (R ^13a ) R ¹³ , -S (O) ₂ N (R ^13a ) R ¹³ , -ON (R ^13a ) R ¹³ , -N (R ^13a ) OR ¹¹ , -Si (R ^9a ) (R ^9b ) R ⁹ , -P (O) (OR ¹⁰ ) ₂ , -P (S) (OR ¹⁰ ) ₂ , -P (phenyl) ₂ , -P (O) (phenyl) ₂ , Phenyl, naphthyl, (Z ² ) _q2 Phenyl substituted with (Z ² ) _q2 Represents naphthyl or D2-1 to D2-102 substituted with
R ⁶ Is C ₁ ~ C ₆ Alkyl, R ¹⁴ Optionally substituted with (C ₁ ~ C ₆ ) Alkyl, C ₃ ~ C ₈ Cycloalkyl, R ¹⁴ Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkyl, C ₂ ~ C ₆ Alkenyl, R ¹⁴ Optionally substituted with (C ₂ ~ C ₆ ) Alkenyl, C ₃ ~ C ₈ Cycloalkenyl, R ¹⁴ Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkenyl, C ₂ ~ C ₆ Alkynyl, R ¹⁴ Optionally substituted with (C ₂ ~ C ₆ ) Alkynyl, -S (O) ₂ R ^11a , -C (O) R ¹² , -C (O) OR ^11a , -C (O) SR ^11a , -C (S) OR ^11a , -C (S) SR ^11a , -C (O) N (R ^13a ) R ¹³ , -C (S) N (R ^13a ) R ¹³ , -S (O) ₂ N (R ^13a ) R ¹³ , -Si (R ^9a ) (R ^9b ) R ⁹ , -P (O) (OR ¹⁰ ) ₂ , -P (S) (OR ¹⁰ ) ₂ , -P (phenyl) ₂ , -P (O) (phenyl) ₂ , Phenyl, naphthyl, (Z ² ) _q2 Phenyl substituted with (Z ² ) _q2 Represents naphthyl or D2-1 to D2-102 substituted with
R ^6a Is C ₁ ~ C ₆ Alkyl, R ¹⁴ Optionally substituted with (C ₁ ~ C ₆ ) Alkyl, C ₃ ~ C ₈ Cycloalkyl, R ¹⁴ Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkyl, C ₂ ~ C ₆ Alkenyl, R ¹⁴ Optionally substituted with (C ₂ ~ C ₆ ) Alkenyl, C ₃ ~ C ₈ Cycloalkenyl, R ¹⁴ Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkenyl, C ₂ ~ C ₆ Alkynyl, R ¹⁴ Optionally substituted with (C ₂ ~ C ₆ ) Alkynyl, phenyl, naphthyl, (Z ² ) _q2 Phenyl substituted with (Z ² ) _q2 Represents naphthyl or D2-1 to D2-102 substituted with
R ⁷ Is a hydrogen atom or R ^6a Represents
R ⁸ And R ^8a Each independently represents a hydrogen atom, cyano, C ₁ ~ C ₆ Alkyl, R ¹⁴ Optionally substituted with (C ₁ ~ C ₆ ) Alkyl, C ₃ ~ C ₈ Cycloalkyl, R ¹⁴ Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkyl, C ₂ ~ C ₆ Alkenyl, R ¹⁴ Optionally substituted with (C ₂ ~ C ₆ ) Alkenyl, C ₃ ~ C ₈ Cycloalkenyl, R ¹⁴ Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkenyl, C ₂ ~ C ₆ Alkynyl, R ¹⁴ Optionally substituted with (C ₂ ~ C ₆ ) Alkynyl, -S (O) ₂ R ^11a , -C (O) R ¹² , -N (R ^13a ) R ¹³ , -C (O) OR ^11a , -C (O) SR ^11a , -C (S) OR ^11a , -C (O) N (R ^13a ) R ¹³ , -C (S) N (R ^13a ) R ¹³ , -S (O) ₂ N (R ^13a ) R ¹³ , -C (R ¹² ) = NOR ¹¹ , -C (R ¹² ) = NN (R ^13a ) R ¹³ , -C (= NOR ^11a ) N (R ^13a ) R ¹³ , -C (= NR ^13b ) OR ^11a , -C (= NR ^13b SR ^11a , -C (= NR ^13b ) N (R ^13a ) R ¹³ , -Si (R ^9a ) (R ^9b ) R ⁹ , -P (O) (OR ¹⁰ ) ₂ , -P (S) (OR ¹⁰ ) ₂ , -P (phenyl) ₂ , -P (O) (phenyl) ₂ , Phenyl, naphthyl, (Z ² ) _q2 Phenyl substituted with (Z ² ) _q2 Represents naphthyl or D2-1 to D2-102 substituted with R, or R ⁸ Is R ^8a Together with = C (R ^8c ) R ^8d , = S (R ^8e ) R ^8f Or = S (= O) (R ^8e ) R ^8f Or R ⁸ Is R ^8a Together with C ₂ ~ C ₇ By forming an alkylene chain of ⁸ And R ^8a May form a 3- to 8-membered ring together with the nitrogen atom to which is bonded, and in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and a halogen atom, C ₁ ~ C ₆ Alkyl group, C ₁ ~ C ₆ Haloalkyl group, C ₁ ~ C ₆ Alkoxy (C ₁ ~ C ₄ ) Alkyl group, C ₁ ~ C ₆ Alkoxy group, C ₁ ~ C ₆ Haloalkoxy group, C ₁ ~ C ₆ Alkylthio, C ₁ ~ C ₆ Alkylsulfinyl, C ₁ ~ C ₆ Alkylsulfonyl, C ₁ ~ C ₆ Haloalkylthio, C ₁ ~ C ₆ Haloalkylsulfinyl, C ₁ ~ C ₆ Haloalkylsulfonyl, -CHO group, C ₁ ~ C ₆ Alkoxycarbonyl group, C ₁ ~ C ₆ Haloalkoxycarbonyl group, C ₁ ~ C ₆ Alkylaminocarbonyl group, C ₁ ~ C ₆ Haloalkylaminocarbonyl group, phenyl group, (Z ² ) _q2 Optionally substituted by a phenyl group, D2-1 to D2-102, an oxo group or a thioxo group substituted by
R ^8b Is a hydrogen atom, cyano, nitro, C ₁ ~ C ₆ Alkyl, R ¹⁴ Optionally substituted with (C ₁ ~ C ₆ ) Alkyl, C ₃ ~ C ₈ Cycloalkyl, R ¹⁴ Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkyl, C ₂ ~ C ₆ Alkenyl, R ¹⁴ Optionally substituted with (C ₂ ~ C ₆ ) Alkenyl, C ₃ ~ C ₈ Cycloalkenyl, R ¹⁴ Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkenyl, C ₂ ~ C ₆ Alkynyl, R ¹⁴ Optionally substituted with (C ₂ ~ C ₆ ) Alkynyl, -S (O) ₂ R ¹¹ , -C (O) R ¹² , -C (O) OR ^11a , -C (O) SR ^11a , -C (S) OR ^11a , -C (S) SR ^11a , -C (S) SR ^11a , -C (O) N (R ^13a ) R ¹³ , -C (S) N (R ^13a ) R ¹³ , -S (O) ₂ N (R ^13a ) R ¹³ , -Si (R ^9a ) (R ^9b ) R ⁹ , -P (O) (OR ¹⁰ ) ₂ , -P (S) (OR ¹⁰ ) ₂ , -P (phenyl) ₂ , -P (O) (phenyl) ₂ , Phenyl, naphthyl, (Z ² ) _q2 Phenyl substituted with (Z ² ) _q2 Represents naphthyl or D2-1 to D2-102 substituted with
R ^8c Is a hydrogen atom, -OR ²⁰ , -S (O) _r R ²⁰ Or -N (R ^22a ) R ²² Represents
R ^8d Is C ₁ ~ C ₆ Alkyl, -OR ²⁰ , -S (O) _r R ²⁰ Or -N (R ^22a ) R ²² Or R ^8c And R ^8d Together C ₄ ~ C ₆ Alkylene chain or C ₄ ~ C ₆ By forming an alkenylene chain, R ^8c And R ^8d May form a 5- to 7-membered ring together with the carbon atom to which is bonded, and in this case, the alkylene chain or alkenylene chain may contain 1 to 3 oxygen atoms, sulfur atoms or nitrogen atoms, and a halogen atom or cyano group , Nitro group, C ₁ ~ C ₆ Alkyl group, C ₁ ~ C ₆ Haloalkyl group, C ₁ ~ C ₆ Alkoxy group, C ₁ ~ C ₆ Haloalkoxy group, C ₁ ~ C ₆ Alkylthio group or C ₁ ~ C ₆ Optionally substituted by a haloalkylthio group,
R ^8e And R ^8f Are each independently R ²³ Optionally substituted with (C ₁ ~ C ₆ ) Alkyl, R ²³ Optionally substituted with (C ₂ ~ C ₆ ) Alkenyl, R ²³ Optionally substituted with (C ₂ ~ C ₆ ) Alkynyl, R ²³ Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkyl, C ₁ ~ C ₆ Alkyl, C ₂ ~ C ₆ Alkenyl, C ₃ ~ C ₆ Alkynyl, C ₃ ~ C ₈ Cycloalkyl, C ₁ ~ C ₆ Haloalkyl, C ₂ ~ C ₆ Haloalkenyl, C ₃ ~ C ₆ Haloalkynyl, C ₃ ~ C ₈ Halocycloalkyl, phenyl, naphthyl, (Z ² ) _q2 Phenyl substituted with (Z ² ) _q2 Represents naphthyl or D2-1 to D2-102 substituted with R, or R ^8e And R ^8f Together C ₄ ~ C ₆ Alkylene chain or C ₄ ~ C ₆ By forming an alkenylene chain, R ^8e And R ^8f May form a 5- to 7-membered ring together with the sulfur atom to which is bonded, and in this case, the alkylene chain or alkenylene chain may contain 1 to 3 oxygen atoms, sulfur atoms or nitrogen atoms, and a halogen atom or cyano group , Nitro group, C ₁ ~ C ₆ Alkyl group, C ₁ ~ C ₆ Haloalkyl group, C ₁ ~ C ₆ Alkoxy group, C ₁ ~ C ₆ Haloalkoxy group, C ₁ ~ C ₆ Alkylthio group or C ₁ ~ C ₆ Optionally substituted by a haloalkylthio group,
R ⁹ , R ^9a And R ^9b Are each independently a hydrogen atom, C ₁ ~ C ₆ Alkyl, C ₁ ~ C ₆ Haloalkyl, C ₁ ~ C ₆ Alkoxy, C ₁ ~ C ₆ Haloalkoxy, C ₁ ~ C ₆ Alkylcarbonyl, C ₁ ~ C ₆ Haloalkylcarbonyl, C ₁ ~ C ₆ Alkoxycarbonyl, C ₁ ~ C ₆ Haloalkoxycarbonyl, phenyl or (Z ² ) _q2 Represents phenyl substituted with
R ¹⁰ Is a hydrogen atom or C ₁ ~ C ₆ Represents alkyl,
R ¹¹ Is cyano, C ₁ ~ C ₆ Alkyl, R ^14a Optionally substituted with (C ₁ ~ C ₆ ) Alkyl, C ₂ ~ C ₆ Alkenyl, R ^14a Optionally substituted with (C ₂ ~ C ₆ ) Alkenyl, C ₂ ~ C ₆ Alkynyl, R ^14a Optionally substituted with (C ₂ ~ C ₆ ) Alkynyl, C ₃ ~ C ₈ Cycloalkyl, R ^14a Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkyl, C ₃ ~ C ₈ Cycloalkenyl, R ^14a Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkenyl, phenyl, naphthyl, (Z ² ) _q2 Phenyl substituted with (Z ² ) _q2 Substituted with naphthyl, D2-1 to D2-102, -S (O) ₂ R ^15a , -C (O) R ¹⁶ , -C (O) OR ^15a , -C (O) SR ^15a , -C (S) OR ^15a , -C (S) SR ^15a , -C (O) N (R ^17a ) R ¹⁷ , -C (S) N (R ^17a ) R ¹⁷ , -S (O) ₂ N (R ^17a ) R ¹⁷ , -Si (R ^9a ) (R ^9b ) R ⁹ , -P (O) (OR ¹⁰ ) ₂ Or -P (S) (OR ¹⁰ ) ₂ Represents
R ^11a Is C ₁ ~ C ₆ Alkyl, R ^14a Optionally substituted with (C ₁ ~ C ₆ ) Alkyl, C ₂ ~ C ₆ Alkenyl, R ^14a Optionally substituted with (C ₂ ~ C ₆ ) Alkenyl, C ₂ ~ C ₆ Alkynyl, R ^14a Optionally substituted with (C ₂ ~ C ₆ ) Alkynyl, C ₃ ~ C ₈ Cycloalkyl, R ^14a Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkyl, C ₃ ~ C ₈ Cycloalkenyl, R ^14a Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkenyl, phenyl, naphthyl, (Z ² ) _q2 Phenyl substituted with (Z ² ) _q2 Represents naphthyl or D2-1 to D2-102 substituted with
R ¹² Is a hydrogen atom or R ^11a Represents
R ¹³ And R ^13a Each independently represents a hydrogen atom, cyano, C ₁ ~ C ₆ Alkyl, R ^14a Optionally substituted with (C ₁ ~ C ₆ ) Alkyl, C ₂ ~ C ₆ Alkenyl, R ^14a Optionally substituted with (C ₂ ~ C ₆ ) Alkenyl, C ₂ ~ C ₆ Alkynyl, R ^14a Optionally substituted with (C ₂ ~ C ₆ ) Alkynyl, C ₃ ~ C ₈ Cycloalkyl, R ^14a Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkyl, C ₃ ~ C ₈ Cycloalkenyl, R ^14a Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkenyl, phenyl, naphthyl, (Z ² ) _q2 Phenyl substituted with (Z ² ) _q2 Substituted with naphthyl, D2-1 to D2-102, -S (O) _r R ¹⁵ , -N (R ^17a ) R ¹⁷ , -C (O) R ¹⁶ , -C (O) OR ^15a , -C (O) SR ^15a , -C (S) OR ^15a , -C (S) SR ^15a , -C (O) N (R ^17a ) R ¹⁷ , -C (S) N (R ^17a ) R ¹⁷ , -S (O) ₂ N (R ^17a ) R ¹⁷ , -C (R ¹⁶ ) = NOR ^15a , -C (R ¹⁶ ) = NN (R ^17a ) R ¹⁷ , -C (= NOR ^15a ) N (R ^17a ) R ¹⁷ , -C (= NR ^17b ) OR ^15a , -C (= NR ^17b SR ^15a , -C (= NR ^17b ) N (R ^17a ) R ¹⁷ , -Si (R ^9a ) (R ^9b ) R ⁹ , -P (O) (OR ¹⁰ ) ₂ Or -P (S) (OR ¹⁰ ) ₂ Or R ¹³ Is R ^13a Together with = C (R ^8c ) R ^8d , = S (R ^8e ) R ^8f Or = S (= O) (R ^8e ) R ^8f Or R ¹³ Is R ^13a Together with C ₂ ~ C ₇ By forming an alkylene chain of ¹³ And R ^13a May form a 3- to 8-membered ring together with the nitrogen atom to which is bonded, and in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and a halogen atom, C ₁ ~ C ₆ Alkyl group, C ₁ ~ C ₆ Haloalkyl group, C ₁ ~ C ₆ Alkoxy (C ₁ ~ C ₄ ) Alkyl group, C ₁ ~ C ₆ Alkoxy group, -CHO group, C ₁ ~ C ₆ Alkoxycarbonyl group, C ₁ ~ C ₆ Haloalkoxycarbonyl group, C ₁ ~ C ₆ Alkylaminocarbonyl group, C ₁ ~ C ₆ Haloalkylaminocarbonyl group, phenyl group, (Z ² ) _q2 Optionally substituted by a phenyl group, D2-1 to D2-102, an oxo group or a thioxo group substituted by
R ^13b Is a hydrogen atom, cyano, nitro, C ₁ ~ C ₆ Alkyl, R ^14a Optionally substituted with (C ₁ ~ C ₆ ) Alkyl, C ₂ ~ C ₆ Alkenyl, R ^14a Optionally substituted with (C ₂ ~ C ₆ ) Alkenyl, C ₂ ~ C ₆ Alkynyl, R ^14a Optionally substituted with (C ₂ ~ C ₆ ) Alkynyl, C ₃ ~ C ₈ Cycloalkyl, R ^14a Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkyl, C ₃ ~ C ₈ Cycloalkenyl, R ^14a Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkenyl, -S (O) _r R ¹⁵ , -C (O) R ¹⁶ , -C (O) OR ^15a , -C (O) N (R ^17a ) R ¹⁷ , -C (S) N (R ^17a ) R ¹⁷ , -S (O) ₂ N (R ^17a ) R ¹⁷ , -Si (R ^9a ) (R ^9b ) R ⁹ , -P (O) (OR ¹⁰ ) ₂ , -P (S) (OR ¹⁰ ) ₂ , Phenyl, naphthyl, (Z ² ) _q2 Phenyl substituted with (Z ² ) _q2 Represents naphthyl or D2-1 to D2-102 substituted with
R ¹⁴ And R ^14a Each independently represents a halogen atom, cyano, nitro, C ₃ ~ C ₈ Cycloalkyl, R ¹⁸ Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkyl, C ₃ ~ C ₈ Cycloalkenyl, R ¹⁸ Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkenyl, -OH, -OR ¹⁵ , -SH, -S (O) _r R ¹⁵ , -S (= NR ^17b ) R ^15a , -S (O) (= NR ^17b ) R ^15a , -N (R ^17a ) R ¹⁷ , -C (O) R ¹⁶ , -C (O) OH, -C (O) OR ^15a , -C (O) SR ^15a , -C (S) OR ^15a , -C (S) SR ^15a , -C (O) N (R ^17a ) R ¹⁷ , -C (S) N (R ^17a ) R ¹⁷ , -C (O) N (R ^17a ) N (R ^17a ) R ¹⁷ , -C (O) N (R ^17a ) OR ^15a , -C (R ¹⁶ ) = NOH, -C (R ¹⁶ ) = NOR ^15a , -C (R ¹⁶ ) = NN (R ^17a ) R ¹⁷ , -C (= NOR ^15a ) N (R ^17a ) R ¹⁷ , -C (= NR ^17b ) OR ^15a , -C (= NR ^17b SR ^15a , -C (= NR ^17b ) N (R ^17a ) R ¹⁷ , -S (O) ₂ N (R ^17a ) R ¹⁷ , -ON (R ^17a ) R ¹⁷ , -N (R ^17a ) OR ^15a , -Si (R ^9a ) (R ^9b ) R ⁹ , -P (O) (OR ¹⁰ ) ₂ , -P (S) (OR ¹⁰ ) ₂ , -P (phenyl) ₂ , -P (O) (phenyl) ₂ , Phenyl, naphthyl, (Z ² ) _q2 Phenyl substituted with (Z ² ) _q2 Represents naphthyl or D2-1 to D2-102 substituted with
R ¹⁵ Is phenyl, naphthyl, (Z ² ) _q2 Phenyl substituted with (Z ² ) _q2 Substituted with naphthyl, D2-1 to D2-102, C ₁ ~ C ₆ Alkyl, R ¹⁹ Optionally substituted with (C ₁ ~ C ₆ ) Alkyl, C ₂ ~ C ₆ Alkenyl, R ¹⁹ Optionally substituted with (C ₂ ~ C ₆ ) Alkenyl, C ₂ ~ C ₆ Alkynyl, R ¹⁹ Optionally substituted with (C ₂ ~ C ₆ ) Alkynyl, C ₃ ~ C ₈ Cycloalkyl, R ¹⁹ Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkyl, C ₃ ~ C ₈ Cycloalkenyl, R ¹⁹ Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkenyl, -S (O) ₂ R ²⁰ , -C (O) R ²¹ , -C (O) OR ²⁰ , -C (O) SR ²⁰ , -C (S) OR ²⁰ , -C (S) SR ²⁰ , -C (O) N (R ^22a ) R ²² , -C (S) N (R ^22a ) R ²² , -S (O) ₂ N (R ^22a ) R ²² , -Si (R ^9a ) (R ^9b ) R ⁹ , -P (O) (OR ¹⁰ ) ₂ Or -P (S) (OR ¹⁰ ) ₂ Represents
R ^15a Is phenyl, naphthyl, (Z ² ) _q2 Phenyl substituted with (Z ² ) _q2 Substituted with naphthyl, D2-1 to D2-102, C ₁ ~ C ₆ Alkyl, R ¹⁹ Optionally substituted with (C ₁ ~ C ₆ ) Alkyl, C ₂ ~ C ₆ Alkenyl, R ¹⁹ Optionally substituted with (C ₂ ~ C ₆ ) Alkenyl, C ₃ ~ C ₈ Cycloalkenyl, R ¹⁹ Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkenyl, C ₂ ~ C ₆ Alkynyl, R ¹⁹ Optionally substituted with (C ₂ ~ C ₆ ) Alkynyl, C ₃ ~ C ₈ Cycloalkyl or R ¹⁹ Optionally substituted with (C ₃ ~ C ₈ ) Represents cycloalkyl,
R ¹⁶ Is a hydrogen atom or R ¹⁵ Represents
R ¹⁷ And R ^17a Each independently represents a hydrogen atom, cyano, -CHO, -S (O). _r R ²⁰ , -N (R ^22a ) R ²² , -C (O) R ²¹ , -C (O) OR ²⁰ , -C (O) SR ²⁰ , -C (S) OR ²⁰ , -C (S) SR ²⁰ , -C (O) N (R ^22a ) R ²² , -C (S) N (R ^22a ) R ²² , -S (O) ₂ N (R ^22a ) R ²² , -C (R ^21a ) = NOR ²⁰ , -C (R ^21a ) = NN (R ^22a ) R ²² , -C (= NOR ²⁰ ) N (R ^22a ) R ²² , -C (= NR ^22b ) OR ^20a , -C (= NR ^22b SR ^20a , -C (= NR ^22b ) N (R ^22a ) R ²² , -Si (R ^9a ) (R ^9b ) R ⁹ , -P (O) (OR ¹⁰ ) ₂ , -P (S) (OR ¹⁰ ) ₂ , Phenyl, naphthyl, (Z ² ) _q2 Phenyl substituted with (Z ² ) _q2 Substituted with naphthyl, D2-1 to D2-102, C ₁ ~ C ₆ Alkyl, R ¹⁹ Optionally substituted with (C ₁ ~ C ₆ ) Alkyl, C ₂ ~ C ₆ Alkenyl, R ¹⁹ Optionally substituted with (C ₂ ~ C ₆ ) Alkenyl, C ₃ ~ C ₈ Cycloalkenyl, R ¹⁹ Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkenyl, C ₂ ~ C ₆ Alkynyl, R ¹⁹ Optionally substituted with (C ₂ ~ C ₆ ) Alkynyl, C ₃ ~ C ₈ Cycloalkyl or R ¹⁹ Optionally substituted with (C ₃ ~ C ₈ ) Represents cycloalkyl or R ¹⁷ Is R ^17a Together with = C (R ^8c ) R ^8d , = S (R ^8e ) R ^8f Or = S (= O) (R ^8e ) R ^8f Or R ¹⁷ Is R ^17a Together with C ₂ ~ C ₇ By forming an alkylene chain of ¹⁷ And R ^17a May form a 3- to 8-membered ring together with the nitrogen atom to which is bonded, and in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and a halogen atom, C ₁ ~ C ₆ Alkyl group, C ₁ ~ C ₆ Haloalkyl group, C ₁ ~ C ₆ Alkoxy (C ₁ ~ C ₄ ) Alkyl group, C ₁ ~ C ₆ Alkoxy group, -CHO group, C ₁ ~ C ₆ Alkoxycarbonyl group, C ₁ ~ C ₆ Haloalkoxycarbonyl group, C ₁ ~ C ₆ Alkylaminocarbonyl group, C ₁ ~ C ₆ Haloalkylaminocarbonyl group, phenyl group, (Z ² ) _q2 Optionally substituted by a phenyl group, D2-1 to D2-102, an oxo group or a thioxo group substituted by
R ^17b Is a hydrogen atom, cyano, nitro, -CHO, -S (O) _r R ²⁰ , -C (O) R ²¹ , -C (O) OR ²⁰ , -C (O) N (R ^22a ) R ²² , -C (S) N (R ^22a ) R ²² , -S (O) ₂ N (R ^22a ) R ²² , -Si (R ^9a ) (R ^9b ) R ⁹ , -P (O) (OR ¹⁰ ) ₂ , -P (S) (OR ¹⁰ ) ₂ , Phenyl, naphthyl, (Z ² ) _q2 Phenyl substituted with (Z ² ) _q2 Substituted with naphthyl, D2-1 to D2-102, C ₁ ~ C ₆ Alkyl, R ¹⁹ Optionally substituted with (C ₁ ~ C ₆ ) Alkyl, C ₂ ~ C ₆ Alkenyl, R ¹⁹ Optionally substituted with (C ₂ ~ C ₆ ) Alkenyl, C ₃ ~ C ₈ Cycloalkenyl, R ¹⁹ Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkenyl, C ₂ ~ C ₆ Alkynyl, R ¹⁹ Optionally substituted with (C ₂ ~ C ₆ ) Alkynyl, C ₃ ~ C ₈ Cycloalkyl or R ¹⁹ Optionally substituted with (C ₃ ~ C ₈ ) Represents cycloalkyl,
R ¹⁸ And R ¹⁹ Each independently represents a halogen atom, cyano, nitro, phenyl, naphthyl, (Z ² ) _q2 Phenyl substituted with (Z ² ) _q2 Substituted with naphthyl, D2-1 to D2-102, C ₃ ~ C ₈ Cycloalkyl, C ₃ ~ C ₈ Halocycloalkyl, C ₃ ~ C ₈ Cycloalkenyl, C ₃ ~ C ₈ Halocycloalkenyl, C ₁ ~ C ₆ Alkoxy, C ₁ ~ C ₆ Haloalkoxy, C ₁ ~ C ₆ Alkylthio, C ₁ ~ C ₆ Haloalkylthio, C ₁ ~ C ₆ Alkylsulfinyl, C ₂ ~ C ₆ Alkenylsulfinyl, C ₁ ~ C ₆ Haloalkylsulfinyl, C ₁ ~ C ₆ Alkylsulfonyl, C ₁ ~ C ₆ Haloalkylsulfonyl, C ₁ ~ C ₆ Alkylcarbonyl, C ₁ ~ C ₆ Haloalkylcarbonyl, C ₁ ~ C ₆ Alkoxycarbonyl, C ₁ ~ C ₆ Haloalkoxycarbonyl, C ₁ ~ C ₆ Alkylaminocarbonyl, C ₁ ~ C ₆ Haloalkylaminocarbonyl, di (C ₁ ~ C ₆ Alkyl) aminocarbonyl, OR ²³ , S (O) _r R ²³ Or C (O) R ²³ Represents
R ²⁰ , R ^20a , R ²¹ And R ^21a Are each independently phenyl, naphthyl, (Z ² ) _q2 Phenyl substituted with (Z ² ) _q2 Naphthyl substituted with D2-1 to D2-102, R ²³ Optionally substituted with (C ₁ ~ C ₆ ) Alkyl, R ²³ Optionally substituted with (C ₂ ~ C ₆ ) Alkenyl, R ²³ Optionally substituted with (C ₂ ~ C ₆ ) Alkynyl, R ²³ Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkyl, R ²³ Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkenyl, C ₁ ~ C ₆ Alkyl, C ₂ ~ C ₆ Alkenyl, C ₂ ~ C ₆ Alkynyl, C ₃ ~ C ₈ Cycloalkyl, C ₁ ~ C ₆ Haloalkyl, C ₂ ~ C ₆ Haloalkenyl, C ₂ ~ C ₆ Haloalkynyl, C ₃ ~ C ₈ Halocycloalkyl or C ₃ ~ C ₈ Represents halocycloalkenyl,
R ²² And R ^22a Each independently represents a hydrogen atom, cyano, —CHO, phenyl, naphthyl, (Z ² ) _q2 Phenyl substituted with (Z ² ) _q2 Naphthyl substituted with D2-1 to D2-102, R ²³ Optionally substituted with (C ₁ ~ C ₆ ) Alkyl, R ²³ Optionally substituted with (C ₂ ~ C ₆ ) Alkenyl, R ²³ Optionally substituted with (C ₂ ~ C ₆ ) Alkynyl, R ²³ Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkyl, R ²³ Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkenyl, C ₁ ~ C ₆ Alkyl, C ₂ ~ C ₆ Alkenyl, C ₂ ~ C ₆ Alkynyl, C ₃ ~ C ₈ Cycloalkyl, C ₁ ~ C ₆ Haloalkyl, C ₂ ~ C ₆ Haloalkenyl, C ₂ ~ C ₆ Haloalkynyl, C ₃ ~ C ₈ Halocycloalkyl, C ₃ ~ C ₈ Halocycloalkenyl, C ₁ ~ C ₆ Alkylsulfonyl, C ₁ ~ C ₆ Haloalkylsulfonyl, C ₁ ~ C ₆ Alkylcarbonyl, C ₁ ~ C ₆ Haloalkylcarbonyl, C ₁ ~ C ₆ Alkoxycarbonyl, C ₁ ~ C ₆ Haloalkoxycarbonyl, -OR ²³ , -S (O) _r R ²³ Or -C (O) R ²³ Represents
R ^22b Is R ²² Or represents nitro,
R ²³ Is phenyl, naphthyl, (Z ² ) _q2 Phenyl substituted with (Z ² ) _q2 Represents naphthyl or D2-1 to D2-102 substituted with
X ² Is a halogen atom, cyano, nitro, -OH, -SH, -NH ₂ , -C (O) NH ₂ , -C (S) NH ₂ , -S (O) ₂ NH ₂ Or R ²⁴ When t1, t2 or t4 represents an integer of 2 or more, each X ² May be the same as or different from each other, and two X ² Are adjacent, the two adjacent X ² Is -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 -, -CH ₂ CH ₂ CH ₂ CH ₂ -, -CH ₂ CH ₂ CH ₂ O-, -CH ₂ CH ₂ OCH ₂ -, -CH ₂ OCH ₂ O-, -OCH ₂ CH ₂ O-, -CH ₂ CH ₂ CH ₂ S- or -OCH ₂ CH ₂ By forming S-, each X ² May form a 5-membered ring or a 6-membered ring together with the carbon atom to which is bonded, and the hydrogen atom bonded to each carbon atom forming the ring is a halogen atom, C ₁ ~ C ₆ Alkyl group, C ₁ ~ C ₆ Haloalkyl group, C ₁ ~ C ₆ Alkoxy group, C ₁ ~ C ₆ Alkylthio group, C ₁ ~ C ₆ An alkylsulfinyl group or C ₁ ~ C ₆ Optionally substituted by an alkylsulfonyl group,
X ^2a Is a hydrogen atom, cyano, -OH, -NH ₂ , -CHO or R ²⁴ X ^2a X next to ² Is adjacent X ^2a And X ² Is -CH ₂ CH ₂ CH ₂ CH ₂ -, -CH = CHCH = CH-, -N = CHCH = CH-, -CH = N-CH = CH-, -CH = CH-N = CH- or -CH = CH-CH = N-. X ^2a And X ² May form a 6-membered ring together with the atoms to which each of them is bonded, and at this time, the hydrogen atom bonded to each carbon atom forming the ring is a halogen atom, C ₁ ~ C ₆ Alkyl group, C ₁ ~ C ₆ Haloalkyl group, C ₁ ~ C ₆ Alkoxy group, C ₁ ~ C ₆ Alkylthio group, C ₁ ~ C ₆ An alkylsulfinyl group or C ₁ ~ C ₆ Optionally substituted by an alkylsulfonyl group,
X ^2b Is a halogen atom, cyano, nitro, -OH, -SH, -NH ₂ , -C (O) NH ₂ , -C (S) NH ₂ , -S (O) ₂ NH ₂ , -CHO or R ²⁴ When u1, u2, u4, u5, u6, u7, u8 or u9 represents an integer of 2 or more, each X ^2b May be the same as or different from each other, and two X ^2b Are substituted on the same carbon, two X ^2b Together oxo, thioxo, imino, C ₁ ~ C ₆ Alkylimino, C ₁ ~ C ₆ Alkoxyimino or C ₁ ~ C ₆ May form alkylidene,
Z ² Is a halogen atom, cyano, nitro, -OH, -SH, -NH ₂ , -C (O) NH ₂ , -C (S) NH ₂ , -S (O) ₂ NH ₂ Or R ²⁴ And when q2 represents an integer of 2 or more, each Z ² May be the same as or different from each other, and two Z ² Are adjacent to each other, two adjacent Z ² Is -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 -, -CH ₂ CH ₂ N (X ^2a )-, -CH ₂ N (X ^2a ) CH ₂ -, -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-, -CH ₂ CH = CH-, -OCH = CH-, -SCH = CH-, -N (X ^2a ) CH = CH-, -OCH = N-, -SCH = N-, -N (X ^2a ) CH = N-, -N (X ^2a ) N = CH-, -OCH ₂ CH = CH-, -N = CHCH = CH-, -CH = NCH = CH-, -N = NCH = CH-, -CH = NN = CH-, -N = CHCH = N- or -N = CHN = By forming CH-, each Z ² May form a 5-membered ring or a 6-membered ring together with the carbon atom to which is bonded, and at this time, the hydrogen atom bonded to each carbon atom forming the ring is a halogen atom, C ₁ ~ C ₆ Alkyl group, C ₁ ~ C ₆ Haloalkyl group, C ₁ ~ C ₆ Alkoxy group, C ₁ ~ C ₆ Alkylthio group, C ₁ ~ C ₆ An alkylsulfinyl group or C ₁ ~ C ₆ Optionally substituted by an alkylsulfonyl group,
R ²⁴ Is C ₁ ~ C ₆ Alkyl, C ₂ ~ C ₆ Alkenyl, C ₂ ~ C ₆ Alkynyl, C ₃ ~ C ₈ Cycloalkyl, R ²⁸ Optionally substituted with (C ₁ ~ C ₆ ) Alkyl, R ²⁸ Optionally substituted with (C ₂ ~ C ₆ ) Alkenyl, R ²⁸ Optionally substituted with (C ₂ ~ C ₆ ) Alkynyl, R ²⁸ Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkyl, R ²⁸ Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkenyl, -OR ²⁵ , -S (O) _r R ²⁵ , -C (O) OR ²⁵ , -C (O) R ²⁶ , -N (R ^27a ) R ²⁷ , -C (O) N (R ^27a ) R ²⁷ , -C (S) N (R ^27a ) R ²⁷ , -S (O) _r N (R ^27a ) R ²⁷ , Phenyl, C ₁ ~ C ₆ Represents phenyl optionally substituted with an alkyl or halogen atom;
R ²⁵ , R ²⁶ And R ^27a Are each independently a hydrogen atom, C ₁ ~ C ₆ Alkyl, C ₁ ~ C ₆ Haloalkyl, C ₃ ~ C ₈ Represents cycloalkyl,
R ²⁷ Is a hydrogen atom, C ₁ ~ C ₆ Alkyl, C ₁ ~ C ₆ Haloalkyl, C ₃ ~ C ₈ Cycloalkyl, C ₁ ~ C ₆ Alkylcarbonyl, C ₃ ~ C ₈ Cycloalkylcarbonyl, C ₁ ~ C ₆ Haloalkylcarbonyl, C ₁ ~ C ₆ Alkoxycarbonyl, C ₁ ~ C ₆ Haloalkoxycarbonyl
Represents
R ²⁸ Is a halogen atom, cyano, nitro, C ₁ ~ C ₆ Alkoxy, C ₁ ~ C ₆ Haloalkoxy, C ₁ ~ C ₆ Alkylthio, C ₁ ~ C ₆ Haloalkylthio, C ₁ ~ C ₆ Alkylsulfinyl, C ₁ ~ C ₆ Haloalkylsulfinyl, C ₁ ~ C ₆ Alkylsulfonyl, C ₁ ~ C ₆ Haloalkylsulfonyl, C ₁ ~ C ₆ Alkylcarbonyl, C ₃ ~ C ₈ Cycloalkylcarbonyl, C ₁ ~ C ₆ Haloalkylcarbonyl, C ₁ ~ C ₆ Alkoxycarbonyl, C ₁ ~ C ₆ Haloalkoxycarbonyl, C ₁ ~ C ₆ Alkylaminosulfonyl, di (C ₁ ~ C ₆ Alkyl) aminosulfonyl, C ₁ ~ C ₆ Alkylamino, di (C ₁ ~ C ₆ Alkyl) amino,
n1, p1, t1, and u1 each independently represents an integer of 0 to 3,
p2, t2 and u2 each independently represent an integer of 0 to 2,
p3 and t3 each independently represents an integer of 0 to 1,
p4, t4 and u4 each independently represent an integer of 0 to 4,
p5 and u5 each independently represent an integer of 0 to 5;
p6 and u6 each independently represent an integer of 0 to 6;
u7 each independently represents an integer of 0 to 7,
p8 represents an integer of 1 to 4,
u8 represents an integer of 0 to 8,
u9 represents an integer of 0 to 9,
q and q2 each independently represent an integer of 1 to 5,
m1, m2, m3 and m4 each independently represents an integer of 0 or 1,
r represents an integer of 0-2. ] The parasite control composition of the animal which contains the pyrazole derivative represented by these, or its salt as an active ingredient.

[2]
(1) ^{A 2} is, D1-1~D1-5, D1-8~D1-14, D1-18~D1-24, D1-28~D1-38 , D1-41, D1-43, D1-46 D1-48, D1-49, D1-52 to D1-68, D1-70 to D1-72, D1-74 to D1-76, D1-79, D1-82 to D1-85, D1-88, D1 -89, D1-91, D1-92 or D1-94 to D1-105, and p1, p2, p3, p4, p5, p6 or p8 represents an integer of 1 or more,
X ¹ is a halogen atom, cyano, nitro, azide, —SCN, —SF ₅ , C ₁ -C ₁₂ alkyl, (C ₁ -C ₁₂ ) alkyl optionally substituted with R ⁵ , C ₃ -C ₁₂ cyclo. alkyl, optionally substituted with ^{R 5} _(C 3 ~C _{12) cycloalkyl,} C 2 _{-C 12} alkenyl, optionally substituted with ^{R 5} _(C 2 ~C _{12) alkenyl,} C 3 _{-C 12} cycloalkyl alkenyl, optionally substituted with ^{R 5} _(C 3 ~C _{12) cycloalkenyl,} C 2 _{-C 12} alkynyl, optionally substituted with ^{R 5} _(C 2 ~C _{12) alkynyl,} C 3 _{-C 12} allenyl _{^{, -OH, -OR 6, -SH,}} -S (O) r R 6, -S (= NR 8b) R 6a, -S (O) (= NR 8b) R 6a, -N (R 8a) R ^{8, -C (O) R 7} , -C (O) ^{H, -C (O) OR 6a} , -C (O) SR 6a, -C (S) OR 6a, -C (S) SR 6a, -C (O) N (R 8a) R 8, -C ( ^{S) N (R 8a) R} 8, -C (O) N (R 8a) N (R 8a) R 8, -C (O) N (R 8a) OR 6, -C (O) C (O) OR ^6a , -C (R ⁷ ) = NOH, -C (R ⁷ ) = NOR ⁶ , -C (R ⁷ ) = NN (R ^8a ) R ⁸ , -C (= NOR ⁶ ) N (R ^8a ) R ^{8, -C (= NR 8b)} OR 6a, -C (= NR 8b) SR 6a, -C (= NR 8b) N (R 8a) R 8, -S (O) 2 OR 6, -S (O ) ₂ N (R ^8a ) R ⁸ , -ON (R ^8a ) R ⁸ , -N (R ^8a ) OR ⁶ , -Si (R ^9a ) (R ^9b ) R ⁹ , -P (O) (OR ¹⁰ ) _2, -P (S ^(OR ₁₀₎ 2, -P _(phenyl) 2, -P (O) _{(phenyl) 2,} phenyl, ^naphthyl, (Z ₂₎ phenyl substituted with ^_q2, (Z ₂₎ is substituted with _q2 naphthyl or D2 -1 to D2-102, and when p1, p2, p4, p5, p6 or p8 represents an integer of 2 or more, each X ¹ may be the same as or different from each other; When two X ¹ are adjacent to each other, the two adjacent X ¹ 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 -, - CH 2 CH 2 CH 2 CH 2 -, - CH 2 CH 2 CH 2 O -, - CH 2 CH 2 OCH 2 -, - CH 2 OCH 2 O _{-, - OCH 2 CH 2 O} -, - CH 2 C By forming H ₂ CH ₂ S— or —OCH ₂ CH ₂ S—, a 5-membered ring or a 6-membered ring may be formed together with the carbon atom to which each X ¹ is bonded. The hydrogen atom bonded to each carbon atom may be optionally replaced by X ² ;
(Provided that one or more of ^X 1 _{^{are, -S (O) r R 11}} , -S (= NR 13b) R 11a, -S (O) (= NR 13b) R 11a, -C (R 12) = NOH and —C (R ¹² ) ═ (C ₁ -C ₁₂ ) alkyl optionally substituted with a substituent selected from the group consisting of NOR ¹¹ ).
(2) ^{A 2} is, D1-6, D1-7, D1-15~D1-17, D1-25~D1-27 , D1-39, D1-40, D1-42, D1-44, D1-45 D1-47, D1-69, D1-73, D1-77, D1-78, D1-80, D1-81, D1-86, D1-87, D1-90 or D1-93, and p1, When p2, p3, p4 or p5 represents an integer of 1 or more,
X ¹ is a halogen atom, cyano, nitro, azide, —SCN, —SF ₅ , C ₁ -C ₁₂ alkyl, (C ₁ -C ₁₂ ) alkyl optionally substituted with R ⁵ , C ₃ -C ₁₂ cyclo. alkyl, optionally substituted with ^{R 5} _(C 3 ~C _{12) cycloalkyl,} C 2 _{-C 12} alkenyl, optionally substituted with ^{R 5} _(C 2 ~C _{12) alkenyl,} C 3 _{-C 12} cycloalkyl alkenyl, optionally substituted with ^{R 5} _(C 3 ~C _{12) cycloalkenyl,} C 2 _{-C 12} alkynyl, optionally substituted with ^{R 5} _(C 2 ~C _{12) alkynyl,} C 3 _{-C 12} allenyl _{^{, -OH, -OR 6, -SH,}} -S (O) r R 6, -S (= NR 8b) R 6a, -S (O) (= NR 8b) R 6a, -N (R 8a) R ^{8, -C (O) R 7} , -C (O) ^{H, -C (O) OR 6a} , -C (O) SR 6a, -C (S) OR 6a, -C (S) SR 6a, -C (O) N (R 8a) R 8, -C ( ^{S) N (R 8a) R} 8, -C (O) N (R 8a) N (R 8a) R 8, -C (O) N (R 8a) OR 6, -C (O) C (O) OR ^6a , -C (R ⁷ ) = NOH, -C (R ⁷ ) = NOR ⁶ , -C (R ⁷ ) = NN (R ^8a ) R ⁸ , -C (= NOR ⁶ ) N (R ^8a ) R ^{8, -C (= NR 8b)} OR 6a, -C (= NR 8b) SR 6a, -C (= NR 8b) N (R 8a) R 8, -S (O) 2 OR 6, -S (O ) ₂ N (R ^8a ) R ⁸ , -ON (R ^8a ) R ⁸ , -N (R ^8a ) OR ⁶ , -Si (R ^9a ) (R ^9b ) R ⁹ , -P (O) (OR ¹⁰ ) _2, -P (S ^(OR ₁₀₎ 2, -P _(phenyl) 2, -P (O) _{(phenyl) 2,} phenyl, ^naphthyl, (Z ₂₎ phenyl substituted with ^_q2, (Z ₂₎ is substituted with _q2 naphthyl or D2 -1 to D2-102, and when p1, p2, p4 or p5 represents an integer of 2 or more, each X ¹ may be the same as or different from each other, and two X ¹ Are adjacent to each other, two adjacent X ¹ 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} -, - CH 2 CH 2 CH 2 CH 2 -, - CH 2 CH 2 CH 2 O -, - CH 2 CH 2 OCH 2 -, - CH 2 OCH 2 O -, - OCH ₂ CH ₂ O—, —CH ₂ CH ₂ CH ₂ By forming S— or —OCH ₂ CH ₂ S—, a 5-membered ring or a 6-membered ring may be formed together with the carbon atom to which each X ¹ is bonded. At this time, each carbon atom forming the ring The hydrogen atom bonded to may be optionally substituted by X ² ,
X ^1a is a hydrogen atom, a halogen atom, cyano, nitro, azide, —SCN, —SF ₅ , C _{1 to} C ₁₂ alkyl, (C _{1 to} C ₁₂ ) alkyl optionally substituted with R ^5a , C ₃ to C ₁₂ ^cycloalkyl, optionally substituted with ^{R 5a} _(C 3 ~C _{12) cycloalkyl,} substituted C 2 _{-C 12} ^alkenyl, optionally with ^{R 5a} _(C 2 ~C _{12) alkenyl, C} 3 ~ C ₁₂ ^{cycloalkenyl,} optionally substituted with ^{R 5a} _(C 3 ~C _{12) cycloalkenyl,} C 2 _{-C 12} ^alkynyl, optionally substituted with ^{R 5a} _(C 2 ~C _{12) alkynyl, C} 3 ~ C _{12 ^{allenyl, -OH, -OR 6, -S (}} O) r R 6, -S (= NR 8b) R 6a, -S (O) (= NR 8b) R 6a, -N (R 8a) R ^8, -C (O) R ^{, -C (O) OR 6a,} -C (O) SR 6a, -C (S) OR 6a, -C (S) SR 6a, -C (O) N (R 8a) R 8, -C (S ) N (R ^8a ) R ⁸ , —C (O) N (R ^8a ) N (R ^8a ) R ⁸ , —C (O) N (R ^8a ) OR ⁶ , —C (O) C (O) OR ^{6a, -C (R 7) =} NOH, -C (R 7) = NOR 6, -C (R 7) = NN (R 8a) R 8, -C (= NOR 6) N (R 8a) R 8 ^{, -C (= NR 8b) OR} 6a, -C (= NR 8b) SR 6a, -C (= NR 8b) N (R 8a) R 8, -S (O) 2 N (R 8a) R 8, ^{-Si (R 9a) (R 9b} ) R 9, -P (O) (OR 10) 2, -P (S) (OR 10) 2, -P ( _phenyl) 2, -P _(O) (phenyl) _2, Fe Le, ^naphthyl, (Z ₂₎ phenyl substituted with ^_q2, represents a (Z ₂₎ naphthyl or D2-1~D2-102 substituted with _q2, ^{further, if X 1} is present at the adjacent position to ^{X 1a} the, ^{X 1a} and ^{X 1} _{adjacent, -CH 2 CH 2 O -,} - CH 2 CH 2 CH 2 CH 2 -, - CH = CHCH = CH -, - N = CHCH = CH -, - CH = By forming N—CH═CH—, —CH═CH—N═CH— or —CH═CH—CH═N—, a 5- or 6-membered ring with the atoms to which each of X ^1a and X ¹ is bonded is formed. At this time, the hydrogen atom bonded to each carbon atom forming the ring may be optionally substituted with a halogen atom, a C ₁ -C ₆ alkyl group or a C ₁ -C ₆ haloalkyl group. (provided that one or more of ^{X 1} or ^{X 1a} is S ^_(O) r ^{R 11,} from ^{-S (= NR 13b) R 11a} , -S (O) (= NR 13b) R 11a, -C (R 12) = NOH and ^-C (R 12) = ^{NOR 11} (C ₁ -C ₁₂ ) alkyl optionally substituted with a substituent selected from the group consisting of )
Parasite control composition as described in said [1].

[3]
(1) ^{A 2} is D1-1, D1-2, D1-5~D1-17, D1-19, D1-20, D1-22~D1-26, D1-28, D1-29, D1-36~ D1-40, D1-42, D1-43, D1-46, D1-48, D1-52 to D1-57, D1-59 to D1-63, D1-67 to D1-70, D1-74, D1- 80-D1-87, D1-94-D1-96, D1-98, D1-99 or D1-103-D1-105, and p1, p2, p3, p4, p5, p6 or p8 is 1 or more It represents an integer, further if a carbon atom on a ² which binds to pyrazole 4-position represented by the carbon atom and the formula (B) on the a ² binding of X ¹ adjacent,
(1-1) X ¹ forms a methylene chain together with R ³ to form a 5-membered ring together with the carbon atom to which X ¹ is bonded, the carbon atom to which R ³ is bonded and the carbon atom to which A ² is bonded. In this case, the methylene chain may contain an oxygen atom, a sulfur atom or a nitrogen atom, and further contains a halogen atom, a cyano group, a nitro group, a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ haloalkyl group, C _{1 to} C ₆ alkoxy group, C _{1 to} C ₆ haloalkoxy group, C _{1 to} C ₆ alkylthio group, C _{1 to} C ₆ haloalkylthio group, —NH ₂ group, C _{1 to} C ₆ alkylamino group, di (C ₁ -C ₆₎ alkylamino group, phenyl, ^naphthyl, (Z ₂₎ phenyl substituted with _^q2, (Z _{2) q2} naphthyl or substituted with D2-1～D2-102, oxo group, thioxo group, an imino Group, Optionally substituted by a C ₁ -C ₆ alkylimino group or a C ₁ -C ₆ alkoxyimino group,
(1-2) X ¹ together with R ³ forms a C ₂ -C ₄ alkylene chain or a C ₂ -C ₄ alkenylene chain, whereby the carbon atom to which X ¹ is bonded and the carbon to which R ³ is bonded A 6- to 8-membered ring is formed together with the atom and the carbon atom to which A ² is bonded. At this time, the alkylene chain or alkenylene chain may contain an oxygen atom or a sulfur atom, and further contains a halogen atom, a cyano group, a nitro group, C _1. -C ₆ alkyl _group, C 1 -C ₆ haloalkyl _group, C 1 -C ₆ alkoxy _group, C 1 -C ₆ haloalkoxy _group, C 1 -C ₆ alkylthio _group, C 1 -C ₆ haloalkylthio group, -NH ₂ groups, C ₁ -C ₆ alkylamino group, di (C ₁ -C ₆ ) alkylamino group, phenyl, naphthyl, phenyl substituted with (Z ² ) _q ² , naphthyl substituted with (Z ² ) _q ² The D2-1～D2-102, oxo group, thioxo group, an imino _group, may be arbitrarily substituted with C 1 -C ₆ alkylimino or _C 1 -C ₆ alkoxyimino group,
Furthermore, when p1, p2, p4, p5, p6 or p8 represents an integer of 2 or more, the remaining X ¹ is a halogen atom, cyano, nitro, azide, —SCN, —SF ₅ , C ₁ -C ₁₂ alkyl. , optionally substituted with ^{R 5} _(C 1 ~C _{12) alkyl,} C 3 _{-C 12} cycloalkyl, optionally substituted with ^{R 5} _(C 3 ~C _{12) cycloalkyl,} C 2 _{-C 12} alkenyl , optionally substituted with ^{R 5} _(C 2 ~C _{12) alkenyl,} C 3 _{-C 12} cycloalkenyl, optionally substituted with ^{R 5} _(C 3 ~C _{12) cycloalkenyl,} C 2 _{-C 12} alkynyl , R ⁵ optionally substituted (C ₂ -C ₁₂ ) alkynyl, C ₃ -C ₁₂ allenyl, —OH, —OR ⁶ , —SH, —S (O) _r R ⁶ , —S (═NR ^8b ) ^R 6a, -S (O) ^{= NR 8b) R 6a, -N} (R 8a) R 8, -C (O) R 7, -C (O) OH, -C (O) OR 6a, -C (O) SR 6a, -C ( ^{S) OR 6a, -C (S} ) SR 6a, -C (O) N (R 8a) R 8, -C (S) N (R 8a) R 8, -C (O) N (R 8a) N ^{(R 8a) R 8, -C} (O) N (R 8a) OR 6, -C (O) C (O) OR 6a, -C (R 7) = NOH, -C (R 7) = NOR 6 ^{, -C (R 7) = NN} (R 8a) R 8, -C (= NOR 6) N (R 8a) R 8, -C (= NR 8b) OR 6a, -C (= NR 8b) SR 6a _{^{, -C (= NR 8b) N}} (R 8a) R 8, -S (O) 2 OR 6, -S (O) 2 N (R 8a) R 8, -ON (R 8a) R 8, -N ^(R 8a) OR ^{6 -Si (R 9a) (R 9b} ) R 9, -P (O) (OR 10) 2, -P (S) (OR 10) 2, -P ( _phenyl) 2, -P _(O) (phenyl) _2, phenyl, ^naphthyl, (Z ₂₎ phenyl substituted with ^_q2, (Z _{2) q2} represents naphthyl or D2-1~D2-102 substituted with, p1, p4, p5, p6 or p8 is 3 or more Each X ¹ may be the same as or different from each other, and when two X ¹ are adjacent to each other, the two adjacent X ¹ 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 —, —CH ₂ CH ₂ CH ₂ CH _{2 -, - CH 2 CH 2 CH} 2 O -, - CH 2 CH 2 OCH _The carbon to which each X ¹ is bonded by forming _2- , —CH ₂ OCH ₂ O—, —OCH ₂ CH ₂ O—, —CH ₂ CH ₂ CH ₂ S— or —OCH ₂ CH ₂ S—. A 5-membered ring or a 6-membered ring may be formed together with the atoms, and at this time, a hydrogen atom bonded to each carbon atom forming the ring may be optionally substituted by X ² ,
(2) ^{A 2} is D1-6, D1-15, D1-25, D1-27, D1-40, D1-44, D1-47, D1-50, D1-73, the D1-86 or D1-93 When representing
X ^1a is, by together with ^{R 3} to form a _C 2 -C ₄ alkylene chain or _C 2 -C ₄ alkenylene ^chain, a carbon atom and ^{A 2} nitrogen atoms and ^{R 3 which X 1a} is attached is bound Forms a 6-8 membered ring with the carbon atom to which is bonded, and at this time, the alkylene chain or alkenylene chain may contain 1 to 3 oxygen atoms, sulfur atoms or nitrogen atoms, and a halogen atom, cyano group, nitro group C ₁ -C ₆ alkyl group, C ₁ -C ₆ haloalkyl group, C ₁ -C ₆ alkoxy group, C ₁ -C ₆ haloalkoxy group, C ₁ -C ₆ alkylthio group, C ₁ -C ₆ haloalkylthio group , -NH _{2 group,} C 1 -C ₆ alkylamino group, di _(C 1 ~C ₆₎ alkylamino group, phenyl, ^naphthyl, (Z ₂₎ phenyl substituted with ^_q2, is substituted with (Z _{2) q2} Naphthyl or D2-1～D2-102, oxo group, thioxo group, an imino _group, may be arbitrarily substituted with C 1 -C ₆ alkylimino or _C 1 -C ₆ alkoxyimino group,
X ¹ is a halogen atom, cyano, nitro, azide, —SCN, —SF ₅ , C ₁ -C ₁₂ alkyl, (C ₁ -C ₁₂ ) alkyl optionally substituted with R ⁵ , C ₃ -C ₁₂ cyclo. alkyl, optionally substituted with ^{R 5} _(C 3 ~C _{12) cycloalkyl,} C 2 _{-C 12} alkenyl, optionally substituted with ^{R 5} _(C 2 ~C _{12) alkenyl,} C 3 _{-C 12} cycloalkyl alkenyl, optionally substituted with ^{R 5} _(C 3 ~C _{12) cycloalkenyl,} C 2 _{-C 12} alkynyl, optionally substituted with ^{R 5} _(C 2 ~C _{12) alkynyl,} C 3 _{-C 12} allenyl _{^{, -OH, -OR 6, -SH,}} -S (O) r R 6, -S (= NR 8b) R 6a, -S (O) (= NR 8b) R 6a, -N (R 8a) R ^{8, -C (O) R 7} , -C (O) ^{H, -C (O) OR 6a} , -C (O) SR 6a, -C (S) OR 6a, -C (S) SR 6a, -C (O) N (R 8a) R 8, -C ( ^{S) N (R 8a) R} 8, -C (O) N (R 8a) N (R 8a) R 8, -C (O) N (R 8a) OR 6, -C (O) C (O) OR ^6a , -C (R ⁷ ) = NOH, -C (R ⁷ ) = NOR ⁶ , -C (R ⁷ ) = NN (R ^8a ) R ⁸ , -C (= NOR ⁶ ) N (R ^8a ) R ^{8, -C (= NR 8b)} OR 6a, -C (= NR 8b) SR 6a, -C (= NR 8b) N (R 8a) R 8, -S (O) 2 OR 6, -S (O ) ₂ N (R ^8a ) R ⁸ , -ON (R ^8a ) R ⁸ , -N (R ^8a ) OR ⁶ , -Si (R ^9a ) (R ^9b ) R ⁹ , -P (O) (OR ¹⁰ ) _2, -P (S ^(OR ₁₀₎ 2, -P _(phenyl) 2, -P (O) _{(phenyl) 2,} phenyl, ^naphthyl, (Z ₂₎ phenyl substituted with ^_q2, (Z ₂₎ is substituted with _q2 naphthyl or D2 -1 to D2-102, and when p1, p2, p4, p5, p6 or p8 represents an integer of 2 or more, each X ¹ may be the same as or different from each other; When two X ¹ are adjacent to each other, the two adjacent X ¹ 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 -, - CH 2 CH 2 CH 2 CH 2 -, - CH 2 CH 2 CH 2 O -, - CH 2 CH 2 OCH 2 -, - CH 2 OCH 2 O _{-, - OCH 2 CH 2 O} -, - CH 2 C By forming H ₂ CH ₂ S— or —OCH ₂ CH ₂ S—, a 5-membered ring or a 6-membered ring may be formed together with the carbon atom to which each X ¹ is bonded. The hydrogen atom bonded to each carbon atom may be optionally replaced by X ² ;
(3) ^{A 2 is, (Z} ₁₎ phenyl or substituted with _q ^(Z ₁₎ represents naphthyl substituted with _q, and q represents an integer of 1 or more, the upper ^{A 2} which further bond ^{Z 1} And the carbon atom on A ² bonded to the 4-position of pyrazole of formula (B) are adjacent to each other, Z ¹ together with R ³ is a C _{2 to} C ₄ alkylene chain or C _{2 to} C By forming a _4- alkenylene chain, a 6-8 membered ring is formed together with the carbon atom to which Z ¹ is bonded, the carbon atom to which R ³ is bonded, and the carbon atom to which A ² is bonded. At this time, the alkylene chain or the alkenylene chain is It may contain an oxygen atom or a sulfur atom, and a halogen atom, a cyano group, a nitro _group, C 1 -C ₆ alkyl _group, C 1 -C ₆ haloalkyl _group, C 1 -C ₆ alkoxy _group, C 1 -C ₆ haloalkoxy _group, C 1 _{~C 6} A Kiruchio _group, C 1 -C ₆ haloalkylthio group, -NH _{2 group,} C 1 -C ₆ alkylamino group, di _(C 1 ~C ₆₎ alkylamino group, phenyl, ^naphthyl, substituted with (Z _{2) q2} Optionally substituted by phenyl, (Z ² ) _q2 substituted naphthyl or D2-1 to D2-102, oxo group, thioxo group, imino group, C ₁ -C ₆ alkylimino group or C ₁ -C ₆ alkoxyimino group May be replaced with
Further, when q represents an integer of 2 or more, the remaining Z ¹ is optionally substituted with a halogen atom, cyano, nitro, azide, —SCN, —SF ₅ , C ₁ -C ₁₂ alkyl, R ⁵ ( C ₁ -C ₁₂ ) alkyl, C ₃ -C ₁₂ cycloalkyl, optionally substituted with R ⁵ (C ₃ -C ₁₂ ) cycloalkyl, C ₂ -C ₁₂ alkenyl, optionally substituted with R ⁵ ( C ₂ -C _{12) alkenyl,} C 3 _{-C 12} cycloalkenyl, substituted optionally substituted with ^{R 5} _(C 3 ~C _{12) cycloalkenyl,} C 2 _{-C 12} alkynyl, optionally with ^{R 5} ( C ₂ -C _{12) alkynyl,} C 3 _{-C 12 ^{allenyl, -OH, -OR 6, -SH,}} -S (O) r R 6, -S (= NR 8b) R 6a, -S (O) ( = NR ^8b ) R ^6a , -N (R ^{8 a) R 8, -C (O} ) R 7, -C (O) OR 6a, -C (O) SR 6a, -C (S) OR 6a, -C (S) SR 6a, -C (O) ^{N (R 8a) R 8,} -C (S) N (R 8a) R 8, -C (O) N (R 8a) N (R 8a) R 8, -C (O) N (R 8a) OR ⁶ , -C (O) C (O) OR ^6a , -C (R ⁷ ) = NOH, -C (R ⁷ ) = NOR ⁶ , -C (R ⁷ ) = NN (R ^8a ) R ⁸ , -C ^{(= NOR 6a) N (R} 8a) R 8, -C (= NR 8b) OR 6a, -C (= NR 8b) SR 6a, -C (= NR 8b) N (R 8a) R 8, -S _{^{(O) 2 OR 6a, -S}} (O) 2 N (R 8a) R 8, -ON (R 8a) R 8, -N (R 8a) OR 6, -Si (R 9a) (R 9b) R ^9, -P (O _{^{(OR 10) 2, -P (}} S) (OR 10) 2, -P ( _phenyl) 2, P (O) _{(phenyl) 2,} phenyl, ^naphthyl, phenyl substituted with (Z _{2) q2,} (Z ² ) represents naphthyl substituted with _q2 or D2-1 to D2-102, and when q represents an integer of 3 or more, each Z ¹ may be the same as or different from each other; When two Z ¹ are adjacent to each other, the two adjacent Z ¹ 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 -, - CH 2 CH 2 N (X 1a) -, - CH 2 N (X 1a) CH 2 -, - 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 -, - CH 2 CH = CH -, - OCH = CH -, - SCH = CH -, - N (X 1a) ^{CH = CH -, - OCH =} N -, - SCH = N -, - N (X 1a) CH = N -, - N (X 1a) N = CH -, - OCH 2 CH = CH -, - N = By forming CHCH = CH-, -CH = NCH = CH-, -N = NCH = CH-, -CH = NN = CH-, -N = CHCH = N- or -N = CHN = CH- A 5-membered ring or a 6-membered ring may be formed together with the carbon atom to which each Z ¹ is bonded. At this time, the hydrogen atom bonded to each carbon atom forming the ring is optionally substituted with Z ² . The parasite control composition as described in [1] above.

[4]
R ¹ , R ³ and R ⁴ each independently represents a hydrogen atom, a halogen atom or C ₁ -C ₆ alkyl;
The parasite control composition according to the above [2], wherein n1 and m1 represent an integer of 0.

[5]
A ² is D1-1, D1-2, D1-5~D1-17, D1-19, D1-20, D1-22~D1-26, D1-28, D1-29, D1-36~D1-40 D1-42, D1-43, D1-46, D1-48, D1-52 to D1-57, D1-59 to D1-63, D1-67 to D1-70, D1-74, D1-80 to D1 -87, D1-94 to D1-96, D1-98, D1-99 or D1-103 to D1-105, and p1, p2, p3, p4, p5, p6 or p8 represents an integer of 1 or more. further if the carbon atom on a ² which binds to pyrazole 4-position represented by the carbon atom and formulas for a ² (B) to bond X ¹ is adjacent, X ¹ is taken together with R ³ to form a _C 2 -C ₄ alkylene chain or _C 2 -C ₄ alkenylene chain Te , To form a 6-8 membered ring with the carbon atom bonded carbon atoms and A ² binding carbon atoms and R ³ for coupling of X ^1, alkylene chain or alkenylene chain at this time, contain an oxygen atom or a sulfur atom Further, a halogen atom, a cyano group, a nitro group, a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ haloalkyl group, a C ₁ -C ₆ alkoxy group, a C ₁ -C ₆ haloalkoxy group, a C ₁ -C ₆ alkylthio group, C ₁ -C ₆ haloalkylthio group, —NH ₂ group, C ₁ -C ₆ alkylamino group, di (C ₁ -C ₆ ) alkylamino group, phenyl, naphthyl, substituted with (Z ² ) _q2 Phenyl, (Z ² ) _q2 substituted naphthyl or D2-1 to D2-102, oxo group, thioxo group, imino group, C ₁ -C ₆ alkylimino group or C ₁ -C ₆ alcohol Optionally substituted by a xyimino group,
Furthermore, when p1, p2, p4, p5, p6 or p8 represents an integer of 2 or more,
The remaining X ¹ is a halogen atom, cyano, nitro, azide, —SCN, —SF ₅ , C ₁ -C ₁₂ alkyl, (C ₁ -C ₁₂ ) alkyl optionally substituted with R ⁵ , C ₃ -C _C12 cycloalkyl, optionally substituted with ^{R 5} _(C 3 ~C _{12) cycloalkyl,} C 2 _{-C 12} alkenyl, optionally substituted with ^{R 5} _(C 2 ~C _{12) alkenyl,} C 3 -C ₁₂ cycloalkenyl, optionally substituted with ^{R 5} _(C 3 ~C _{12) cycloalkenyl,} C 2 _{-C 12} alkynyl, optionally substituted with ^{R 5} _(C 2 ~C _{12) alkynyl,} C 3 -C ₁₂ allenyl, —OH, —OR ⁶ , —SH, —S (O) _r R ⁶ , —S (═NR ^8b ) R ^6a , —S (O) (═NR ^8b ) R ^6a , —N (R ^{8a) ) R 8, -C (O)} R 7, -C ^{O) OH, -C (O)} OR 6a, -C (O) SR 6a, -C (S) OR 6a, -C (S) SR 6a, -C (O) N (R 8a) R 8, - ^{C (S) N (R 8a} ) R 8, -C (O) N (R 8a) N (R 8a) R 8, -C (O) N (R 8a) OR 6, -C (O) C ( O) OR ^6a , -C (R ⁷ ) = NOH, -C (R ⁷ ) = NOR ⁶ , -C (R ⁷ ) = NN (R ^8a ) R ⁸ , -C (= NOR ⁶ ) N (R ^{8a ) R 8, -C (= NR} 8b) OR 6a, -C (= NR 8b) SR 6a, -C (= NR 8b) N (R 8a) R 8, -S (O) 2 OR 6, -S _{^{(O) 2 N (R 8a}} ) R 8, -ON (R 8a) R 8, -N (R 8a) OR 6, -Si (R 9a) (R 9b) R 9, -P (O) (OR ¹⁰⁾ _2, - _{^{(S) (OR 10) 2}} , -P ( _phenyl) 2, -P (O) _{(phenyl) 2,} phenyl, ^naphthyl, phenyl substituted with (Z _{2) ^q2,} substituted with (Z _{2) q2} Naphthyl or D2-1 to D2-102,
X ^1a is a hydrogen atom, a halogen atom, cyano, nitro, azide, —SCN, —SF ₅ , C _{1 to} C ₁₂ alkyl, (C _{1 to} C ₁₂ ) alkyl optionally substituted with R ^5a , C ₃ to C ₁₂ ^cycloalkyl, optionally substituted with ^{R 5a} _(C 3 ~C _{12) cycloalkyl,} substituted C 2 _{-C 12} ^alkenyl, optionally with ^{R 5a} _(C 2 ~C _{12) alkenyl, C} 3 ~ C ₁₂ ^{cycloalkenyl,} optionally substituted with ^{R 5a} _(C 3 ~C _{12) cycloalkenyl,} C 2 _{-C 12} ^alkynyl, optionally substituted with ^{R 5a} _(C 2 ~C _{12) alkynyl, C} 3 ~ C _{12 ^{allenyl, -OH, -OR 6, -S (}} O) r R 6, -S (= NR 8b) R 6a, -S (O) (= NR 8b) R 6a, -N (R 8a) R ^8, -C (O) R ^{, -C (O) OR 6a,} -C (O) SR 6a, -C (S) OR 6a, -C (S) SR 6a, -C (O) N (R 8a) R 8, -C (S ) N (R ^8a ) R ⁸ , —C (O) N (R ^8a ) N (R ^8a ) R ⁸ , —C (O) N (R ^8a ) OR ⁶ , —C (O) C (O) OR ^{6a, -C (R 7) =} NOH, -C (R 7) = NOR 6, -C (R 7) = NN (R 8a) R 8, -C (= NOR 6) N (R 8a) R 8 ^{, -C (= NR 8b) OR} 6a, -C (= NR 8b) SR 6a, -C (= NR 8b) N (R 8a) R 8, -S (O) 2 N (R 8a) R 8, ^{-Si (R 9a) (R 9b} ) R 9, -P (O) (OR 10) 2, -P (S) (OR 10) 2, -P ( _phenyl) 2, -P _(O) (phenyl) _2, Fe Le, ^naphthyl, (Z ₂₎ phenyl substituted with _^q2, (Z _{2) q2} parasite control composition described in [3] representing the naphthyl or D2-1~D2-102 substituted with.

[6]
A ¹ represents -CR ¹
R ¹ and R ⁴ each independently represent a hydrogen atom, a halogen atom or C ₁ -C ₆ alkyl;
B represents a ring represented by any one of B-1 to B-6,

A ³ represents —O—, —S (O) _r1 —, —C (X ^1b ) X ^1c —,
X ^1b and X ^1c are each independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ haloalkyl group, a C ₁ -C ₆ alkoxy group, a C _1- C ₆ haloalkoxy group, C ₁ -C ₆ alkylthio group, C ₁ -C ₆ haloalkylthio group, —NH ₂ group, C ₁ -C ₆ alkylamino group, di (C ₁ -C ₆ ) alkylamino group, phenyl , ^naphthyl, (Z ₂₎ phenyl substituted with _^q2, (Z _{2) q2} at or represents naphthyl or D2-1~D2-102 substituted, or ^{X 1b} and ^{X 1c} is an oxo group together, thioxo group, an imino _group, may form a C 1 -C ₆ alkylimino or _C 1 -C ₆ alkoxyimino group,
X ^1d and X ^1f are each independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ haloalkyl group, a C ₁ -C ₆ alkoxy group, a C _1- C ₆ haloalkoxy group, C ₁ -C ₆ alkylthio group, C ₁ -C ₆ haloalkylthio group, —NH ₂ group, C ₁ -C ₆ alkylamino group, di (C ₁ -C ₆ ) alkylamino group, phenyl , ^naphthyl, (Z ₂₎ phenyl substituted with ^_q2, (Z ₂₎ or represents naphthyl or D2-1~D2-102 substituted with _q2, or ^{X 1d} and ^{X 1f} is an oxo group together, thioxo group, an imino _group, may form a C 1 -C ₆ alkylimino or _C 1 -C ₆ alkoxyimino group,
n represents an integer of 1 to 2,
n1 represents an integer of 0;
The parasite control composition according to the above [5], wherein r and r1 each independently represents an integer of 0 to 2.

[7]
X ^1b and X ^1c are each independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ haloalkyl group, a C ₁ -C ₆ alkoxy group, a C _1- C ₆ haloalkoxy group, C ₁ -C ₆ alkylthio group, C ₁ -C ₆ haloalkylthio group, —NH ₂ group, C ₁ -C ₆ alkylamino group, di (C ₁ -C ₆ ) alkylamino group ,
X ^1d and X ^1f are each independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ haloalkyl group, a C ₁ -C ₆ alkoxy group, a C _1- C ₆ haloalkoxy group, C ₁ -C ₆ alkylthio group, C ₁ -C ₆ haloalkylthio group, —NH ₂ group, C ₁ -C ₆ alkylamino group, di (C ₁ -C ₆ ) alkylamino group ,
X ¹ is halogen atom, cyano group, nitro group, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted with R ⁵ , C ₃ -C ₈ cycloalkyl, optionally with R ⁵ substituted _(C 3 ~C _{8) cycloalkyl,} C 2 -C ₆ alkenyl, optionally substituted with ^{R 5} _(C 2 ~C _{6) alkenyl,} C 3 -C ₈ cycloalkenyl, optionally by ^{R 5} substituted _(C 3 ~C _{8) cycloalkenyl,} C 2 -C ₆ alkynyl, optionally substituted with ^{R 5} _(C 2 ~C ₆₎ alkynyl, ^phenyl, phenyl substituted with (Z _{2) q2,} D2-32, D2-33, D2-34, D2-36, D2-37 or D2-38,
X ^1a represents a hydrogen _atom, C 1 -C ₆ alkyl, optionally substituted with ^{R 5a} _(C 1 ~C _{6) alkyl,} C 3 -C ₈ cycloalkyl, optionally substituted with ^{R 5a} _{(C 3} -C _{8) cycloalkyl,} C 2 -C ₆ alkenyl, optionally substituted with ^{R 5a} _(C 2 ~C _{6) alkenyl,} C 3 -C ₈ cycloalkenyl, optionally substituted with ^{R 5a} _{(C 3} -C _{8) cycloalkenyl,} optionally substituted with C 2 -C ₆ alkynyl, or ^{R 5a} _(C 2 ~C ₆₎ alkynyl,
R ⁵ and R ^5a are each independently a halogen atom, cyano, C ₃ -C ₈ cycloalkyl, —OH, —OR ^11, —SH, —S (O) _r R ¹¹ , —S (═NR ^13b ). R ^11a , —S (O) (═NR ^13b ) R ^11a , —N (R ^13a ) R ¹³ , —C (O) R ¹² , —C (O) OR ^11a , —C (O) N (R ^13a ) ) R ¹³ , -C (R ₁₂ ) = NOH or -C (R ₁₂ ) = NOR ₁₁
X ² represents a halogen atom, cyano, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, —OR ²⁵ or —S (O) _r R ²⁵ ,
Z ² represents a halogen atom, cyano, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, —OR ²⁵ or —S (O) _r R ²⁵ ,
R ¹¹ and R ^11a each independently represent C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl or C ₃ -C ₈ cycloalkyl,
R ¹² , R ¹³ , R ^13a and R ^13b are each independently a hydrogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl or C _3. It represents -C ₈ cycloalkyl,
R ²⁵ represents a hydrogen atom, C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
t1 and t4 each independently represents an integer of 0 to 2,
q2 represents an integer of 1 to 2,
The parasite control composition according to the above [6], wherein n represents an integer of 1.

[8]
R ¹ and R ⁴ represent a hydrogen atom,
B represents a ring represented by any of B-1a, B-2a, B-2b, B-3a to B-5a,

X ¹ represents (C ₁ -C ₆ ) alkyl or D2-37 optionally substituted with R ⁵ ,
X ^1a represents a hydrogen atom or (C ₁ -C ₆ ) alkyl optionally substituted with R ^5a ,
X ^1b and X ^1c each independently represent a hydrogen atom or C ₁ -C ₆ alkyl,
R ⁵ represents —S (O) _r R ¹¹ ,
R ^5a represents a halogen atom, cyano, —OR ¹¹ or —S (O) _r R ¹¹ ,
R ¹¹ represents C ₁ -C ₆ alkyl,
The parasite control composition according to the above [7], wherein m1 and t1 are 0.

[9]
R ¹ and R ⁴ represent a hydrogen atom,
(1) A ² represents D1-14, D1-31, D1-34, D1-35, D1-52, D1-57 or D1-68, and p1, p3, p4 or p8 represents an integer of 1. If
X ¹ represents (C ₁ -C ₆ ) alkyl optionally substituted with R ⁵ ,
R ⁵ represents —S (O) _r R ¹¹ ,
R ¹¹ represents C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
r represents an integer of 0 to 2;
(2) if ^{A 2} is, to represent the D1-15 or D1-17, p2 represents an integer of 1,
X ¹ represents (C ₁ -C ₆ ) alkyl optionally substituted with R ⁵ ,
X ^1a _is, represent a C 1 -C ₆ alkyl or _C 1 -C ₆ haloalkyl, ^{or, when X 1} is present at the adjacent position to ^{X 1a} is, ^{X 1a} and ^{X 1} adjacent the -CH ₂ By forming CH ₂ O—, a 5-membered ring may be formed with the atom to which each of X ^1a and X ¹ is bonded,
R ⁵ represents —S (O) _r R ¹¹ ,
R ¹¹ represents C ₁ -C ₆ alkyl,
r represents an integer of 0 to 2;
(3) ^{A 2} is, D1-15, represents D1-16 or D1-17, if p2 represents an integer of 0,
X ^1a represents (C ₁ -C ₆ ) alkyl or —C (O) R ⁷ optionally substituted with R ^5a ,
R ^5a represents -S (O) _r R ¹¹ , -C (R ¹² ) = NOR ¹¹ , -S (= NR ^13b ) R ^11a or -S (O) (= NR ^13b ) R ^11a ,
R ⁷ represents (C ₁ -C ₆ ) alkyl optionally substituted with R ¹⁴ ;
R ¹¹ represents C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl or —C (O) R ¹⁶ ,
R ^11a , R ¹² , R ¹⁵ and R ¹⁶ each independently represent C ₁ -C ₆ alkyl;
R ^13b represents cyano,
R ¹⁴ represents -S (O) _r R ¹⁵ ;
The parasite control composition according to the above [4], wherein r represents an integer of 0 to 2.

[10]
The parasite control composition according to any one of [1] to [9], which is orally administered to an animal.

[11]
The parasite control composition according to any one of [1] to [9], which is administered parenterally to an animal.

[12]
The parasite control composition as described in [11] above, wherein the parenteral administration method to animals is administration by injection or transdermal administration.

[13]
The parasite control composition according to any one of [1] to [12], wherein the animal is a mammal.

[14]
Mammals are rabbit, guinea pig, hamster, gerbil, mouse, rat, squirrel, monkey, dog, ferret, cat, yak, cow, buffalo, goat, sheep, antelope, deer, reindeer, boar, pig, camel, alpaca, llama Parasitic control composition as described in said [13] which is a donkey, a horse, or a kangaroo.

[15]
The parasite control composition according to any one of [1] to [14] above, wherein the parasite is an ectoparasite invertebrate animal.

[16]
Parasitism according to [15] above, wherein the animal's ectoparasite invertebrate is a fly, ab, nukaka, buyu, mosquito, flea, lice, lice, mites, mites, mites, mites, mites, ticks, mites, or mites Insect control composition.

[17]
A method for controlling parasites, wherein an effective amount of the parasite control composition according to any one of [1] to [9] is orally administered to an animal.

[18]
A method for controlling parasites, wherein an effective amount of the parasite control composition according to any one of [1] to [9] is administered parenterally to an animal.

[19]
The method for controlling parasites according to the above [18], wherein the parenteral administration method is administration by injection or transdermal administration.

[20]
The parasite control method according to any one of [17] to [19], wherein the animal is a mammal.

[21]
Mammals are rabbit, guinea pig, hamster, gerbil, mouse, rat, squirrel, monkey, dog, ferret, cat, yak, cow, buffalo, goat, sheep, antelope, deer, reindeer, boar, pig, camel, alpaca, llama The method for controlling parasites according to the above [20], which is a donkey, horse or kangaroo.

[22]
The method for controlling parasites according to any one of [17] to [21] above, wherein the parasite is an ectoparasite invertebrate animal.

[23]
Parasitism according to [22] above, wherein the animal's ectoparasite invertebrate is a fly, ab, nukaka, buyu, mosquito, flea, lice, lice, mites, mites, mites, mites, mites, ticks, mites, or mites Insect control method.

  The present invention provides a parasite control agent that exhibits an excellent control effect against external or internal parasites such as companion animals, pet animals, mammals as domestic animals and poultry, and birds.

  The term “animal” in the present invention refers to companion animals, pets, livestock, poultry, and vertebrates used as research / experimental animals, and more specifically mammals, birds, reptiles, fishes, and the like.

  The term “companion animal / compete animal” in the present invention is intended to enhance human life such as to soothe or entertain a person's heart, to appreciate its appearance and cry, and to be a companion in living. Mammals such as rabbits, gerbils, squirrels, monkeys, dogs, ferrets, cats, etc., juvenile pine, bun butterfly, canary, bred for the purpose of helping the visually impaired, hearing impaired, people with motor impairments, etc. Birds such as cockatiels and budgerigars, reptiles such as turtles, iguanas, lizards, and snakes, and appreciation fish such as goldfish and tropical fish.

  The “livestock / poultry” in the present invention is a rabbit which is artificially bred and raised for the purpose of producing meat, milk, butter, eggs, fur, leather, feathers, wool, etc., or for the purpose of use such as agriculture. It means mammals such as dairy cattle, beef cattle, buffalo, goats, sheep, pigs, camels, horses and donkeys, and birds such as ducks, geese, turkeys and chickens.

  The term “research / experimental animal” as used in the present invention means a rabbit that has been bred and produced for the purpose of research, development of medicines, animal drugs, agricultural chemicals, etc. , Mammals such as guinea pigs, hamsters, gerbils, mice, rats, monkeys, dogs, ferrets, minipigs.

  The term “pest” or “parasite” in the present invention means that it parasitizes the body surface or each organ of the host animal, impairs the healthy growth of the host animal, and sometimes transmits serious diseases. Represents a harmful invertebrate that can lead to death, more specifically, ab, flies, mosquitoes, flyfish, nukaka, fleas, lice, lice, spider mites, hymenids that directly injure or suck skin tissue, hair, and feathers , Ectoparasites typified by arthropods such as tick, tick, mite, tick, tick, tick mite, etc. and capillary nematodes, whipworms that parasitize organs such as stomach, intestine, lung, vein, lymphoid tissue, subcutaneous tissue , Trichinella, Roundworm, Helminth, Fecal nematode, Helminth, Schistosoma, Lungworm, Roundworm, Intestinal nodule, Ciliate nematode, Medina, Filiform, etc. Tapeworms, flukes, spores, ciliates, flagellates Means and internal parasites.

  The term “control” or “control” in the present invention refers to an animal that serves as a host by preventing parasite infection and proliferation by manifesting effects such as repelling, behavioral abnormality induction, mating disruption, feeding / blood sucking inhibition, growth inhibition, lethality, etc. It means to prevent from parasite harm.

  The “control method” in the present invention means to administer a parasite control agent composition to an animal using a method such as oral administration, parenteral administration or administration by a molded product in order to control parasites, Parenteral administration includes subcutaneous injection, intramuscular injection, intraperitoneal injection, intravenous injection, etc., implantation (Inplants), drug bath or immersion, washing, spraying, dropping (Pour-on), spotting (Spot-on) and dusting, etc., transdermal administration, nasal administration, suppository administration, etc., and administration by molded products include neck collars, halters, tails Examples include administration using labeling devices such as Tail bands, Limb bands, and Ear tags.

  The pyrazole derivative represented by the general formula (1), which is an active ingredient of the parasite control agent of the present invention, may have E- and Z-form geometric isomers depending on the type of substituent. The present invention includes these E-form, Z-form, or a mixture containing the E-form and Z-form in any proportion. Further, the pyrazole derivative represented by the general formula (1) which is an active ingredient of the parasite control agent of the present invention has an optically active substance resulting from the presence of one or more asymmetric carbon atoms. The present invention includes all optically active substances or racemates.

  Among the pyrazole derivatives represented by the general formula (1), which are active ingredients of the parasite control agent of the present invention, those that can be converted into acid addition salts according to conventional methods include, for example, hydrofluoric acid, hydrochloric acid, Hydrohalic acid salts such as hydrobromic acid and hydroiodic acid, inorganic acid salts such as nitric acid, sulfuric acid, phosphoric acid, chloric acid and perchloric acid, methanesulfonic acid, ethanesulfonic acid, trifluoromethanesulfonic acid, Salts of sulfonic acids such as benzenesulfonic acid and p-toluenesulfonic acid, formic acid, acetic acid, propionic acid, trifluoroacetic acid, fumaric acid, tartaric acid, succinic acid, maleic acid, malic acid, succinic acid, benzoic acid, mandelic acid, ascorbine A salt of a carboxylic acid such as acid, lactic acid, gluconic acid or citric acid, or a salt of an amino acid such as glutamic acid or aspartic acid can be used.

  Alternatively, among the pyrazole derivatives represented by the general formula (1), which are active ingredients of the parasite control agent of the present invention, those that can be converted into a metal salt according to a conventional method include, for example, lithium, sodium, and potassium. Alkali metal salts, alkaline earth metal salts such as calcium, barium and magnesium, or aluminum salts can be used.

  Next, specific examples of each substituent shown in the present specification are shown below. Here, n- represents normal, i- represents iso, s- represents secondary, and tert- represents tertiary, and Ph represents phenyl.

  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.

The notation of C _a -C _b alkyl in the present specification represents a linear or branched hydrocarbon group having a carbon number of _a to _b , for example, methyl group, ethyl group, n-propyl group, Specific examples include i-propyl group, n-butyl group, i-butyl group, s-butyl group, tert-butyl group, n-pentyl group, 1,1-dimethylpropyl group, n-hexyl group, and the like. Each selected range of carbon atoms is selected.

In the present specification, C _a -C _b haloalkyl is represented by a linear 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. Represents a hydrocarbon group, and when substituted by two or more halogen atoms, the 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, 2-fluoroethyl group, 2- Chloroethyl group, 2-bromoethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, 2-chloro-2,2-difluoroethyl group, 2,2,2-trichloroethyl group, 1 , 1,2,2-tetrafluoroethyl group, 2-chloro-1,1,2-trifluoroethyl group, pentafluoroethyl group, 3,3,3-trifluoropropyl group, 2,2,3,3 , 3-pentafluoropropyl group, 1,1,2,3,3,3-hexafluoropropyl group, heptafluoropropyl group 2,2,2-trifluoro-1- (trifluoromethyl) ethyl group, 1,2,2,2-tetrafluoro-1- (trifluoromethyl) ethyl group, 2,2,3,3,4, Specific examples include 4,4-heptafluorobutyl group, nonafluorobutyl group and the like, and each is selected within the range of the number of carbon atoms designated.

In the present specification, C _a -C _b cycloalkyl represents a cyclic hydrocarbon group having a carbon number of _a to _b , and forms a monocyclic or complex ring structure having 3 to 6 members. I can do it. 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, 1-methylcyclopropyl group, 2-methylcyclopropyl group, 2,2-dimethylcyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, etc. Selected in a range of numbers.

In the present specification, C _a -C _b halocycloalkyl is a cyclic hydrocarbon group 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 can form monocyclic or complex ring structures from 3 to 6-membered rings. 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, 2,2-difluorocyclopropyl group, 2,2-dichlorocyclopropyl group, 2,2-dibromocyclopropyl group, 2,2-difluoro-1-methylcyclopropyl group, 2,2-dichloro-1-methyl Specific examples include cyclopropyl group, 2,2-dibromo-1-methylcyclopropyl group, 2,2,3,3-tetrafluorocyclobutyl group, and the like, and each is selected within the range of the designated number of carbon atoms. The

In the present specification, C _a -C _b alkenyl is a linear or branched chain composed of _a to _b carbon atoms and has one or more double bonds in the molecule. Represents a saturated hydrocarbon group, for example, vinyl group, 1-propenyl group, 2-propenyl group, 1-methylethenyl group, 2-butenyl group, 2-methyl-2-propenyl group, 3-methyl-2-butenyl group, 1 , 1-dimethyl-2-propenyl group 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, C _a -C _b haloalkenyl is a linear or branched chain in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom, and the number of carbon atoms is ab. 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, 2,2-dichlorovinyl group, 2-fluoro-2-propenyl group, 2-chloro-2-propenyl group, 3-chloro-2-propenyl group, 2-bromo-2-propenyl group, 3,3-difluoro -2-propenyl group, 2,3-dichloro-2-propenyl group, 3,3-dichloro-2-propenyl group, 2,3,3-trifluoro-2-propenyl group, 2,3,3-trichloro- 2-propenyl group, 1- (trifluoromethyl) ethenyl group, 4,4-difluoro-3-butenyl group, 3,4,4-trifluoro-3-butenyl group, 3-chloro-4,4,4- Specific examples include a trifluoro-2-butenyl group and the like, and each is selected within the range of the designated number of carbon atoms.

The notation of C _a -C _b cycloalkenyl in the present specification represents a cyclic unsaturated hydrocarbon group having 1 to 2 carbon atoms and having 1 or 2 or more double bonds. A monocyclic or complex ring structure from a member ring to a 6-member 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-cyclopenten-1-yl group, 2-cyclopenten-1-yl group, 1-cyclohexen-1-yl group, 2-cyclohexen-1-yl group, and the like. Selected in a range of numbers.

In the present specification, C _a -C _b halocycloalkenyl has the following notation: a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom, a cyclic one having 1 to b carbon atoms, and one Alternatively, it represents an unsaturated hydrocarbon group having two or more double bonds, and can form a monocyclic or complex ring structure having 3 to 6 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-. In addition, the substitution by a halogen atom may be a ring structure part, a side chain part or both of them, and when substituted by two or more halogen atoms, those halogen atoms May be the same as or different from each other. For example, 2-fluoro-1-cyclopentenyl group, 2-chloro-1-cyclopentenyl group, 3-chloro-2-cyclopentenyl group, 2-fluoro-1-cyclohexenyl group and the like can be mentioned as specific examples. Selected within the specified number of carbon atoms.

In the present specification, 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, such as methylidene group, ethylidene Specific examples include a group, a propylidene group, a 1-methylethylidene group, and the like, and each group is selected within the range of the designated number of carbon atoms.

In the present specification, C _a -C _b alkynyl is a linear or branched chain composed of _a to _b carbon atoms and has one or more triple bonds in the molecule. Represents a hydrocarbon group, for example, ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1,1-dimethyl-2-propynyl group, etc. Each of which is selected for each specified number of carbon atoms.

In the present specification, C _a -C _b haloalkynyl represents a linear or branched chain in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom, and the number of carbon atoms is a to b. 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. Specific examples include 2-chloroethynyl group, 2-bromoethynyl group, 2-iodoethynyl group, 3-chloro-2-propynyl group, 3-bromo-2-propynyl group, 3-iodo-2-propynyl group and the like. Each of which is selected for each specified number of carbon atoms.

The notation of 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 group, Specific examples include an i-propyloxy group, an n-butyloxy group, an i-butyloxy group, an s-butyloxy group, a tert-butyloxy group, and the like, and each is selected within the range of the designated number of carbon atoms.

The notation of C _a -C _b haloalkoxy in the present specification represents a haloalkyl-O— group having the above-mentioned meaning consisting of _a to _b carbon atoms, for example, difluoromethoxy group, trifluoromethoxy group, chlorodifluoro Methoxy group, bromodifluoromethoxy group, 2-fluoroethoxy group, 2-chloroethoxy group, 2,2,2-trifluoroethoxy group, 1,1,2,2, -tetrafluoroethoxy group, 2-chloro-1 Specific examples include 1,2,2-trifluoroethoxy group, 1,1,2,3,3,3-hexafluoropropyloxy group and the like, and each is selected within the range of the designated number of carbon atoms.

The notation of C _a -C _b alkylthio in the present specification 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, i Specific examples include -propylthio group, n-butylthio group, i-butylthio group, s-butylthio group, tert-butylthio group and the like, which are selected within the range of the number of carbon atoms specified.

The notation of C _a -C _b haloalkylthio in the present specification represents a haloalkyl-S-group having the above-mentioned meaning consisting of _a to _b carbon atoms, for example, difluoromethylthio group, trifluoromethylthio group, chlorodifluoro Methylthio group, bromodifluoromethylthio group, 2,2,2-trifluoroethylthio group, 1,1,2,2-tetrafluoroethylthio group, 2-chloro-1,1,2-trifluoroethylthio group, Pentafluoroethylthio group, 1,1,2,3,3,3-hexafluoropropylthio group, heptafluoropropylthio group, 1,2,2,2-tetrafluoro-1- (trifluoromethyl) ethylthio group , Nonafluorobutylthio group and the like are given as specific examples, and each is selected within the range of the designated number of carbon atoms.

The notation of C _a -C _b alkylsulfinyl in the present specification represents an alkyl-S (O) -group having the above-mentioned meaning consisting of _a to _b carbon atoms, for example, methylsulfinyl group, ethylsulfinyl group, Specific examples include n-propylsulfinyl group, i-propylsulfinyl group, n-butylsulfinyl group, i-butylsulfinyl group, s-butylsulfinyl group, tert-butylsulfinyl group and the like. The range is selected.

In the present specification, the expression C _a -C _b haloalkylsulfinyl represents a haloalkyl-S (O) -group having the above-mentioned meaning consisting of _a to _b carbon atoms, for example, difluoromethylsulfinyl group, trifluoromethyl Sulfinyl group, chlorodifluoromethylsulfinyl group, bromodifluoromethylsulfinyl group, 2,2,2-trifluoroethylsulfinyl group, 1,2,2,2-tetrafluoro-1- (trifluoromethyl) ethylsulfinyl group, nona Specific examples include a fluorobutylsulfinyl group and the like, and each is selected within the range of the designated number of carbon atoms.

The notation of C _a -C _b alkylsulfonyl in the present specification represents an alkyl-SO ₂ -group having the above-mentioned meaning consisting of _a to _b carbon atoms, for example, methylsulfonyl group, ethylsulfonyl group, n- Specific examples include a propylsulfonyl group, an i-propylsulfonyl group, an n-butylsulfonyl group, an i-butylsulfonyl group, an s-butylsulfonyl group, a tert-butylsulfonyl group, and the range of each designated number of carbon atoms. Selected.

The notation of C _a -C _b haloalkylsulfonyl in the present specification represents a haloalkyl-SO ₂ -group having the above-mentioned meaning consisting of _a to _b carbon atoms, such as a difluoromethylsulfonyl group or a trifluoromethylsulfonyl group. Chlorodifluoromethylsulfonyl group, bromodifluoromethylsulfonyl group, 2,2,2-trifluoroethylsulfonyl group, 1,1,2,2-tetrafluoroethylsulfonyl group, 2-chloro-1,1,2-trimethyl Specific examples include a fluoroethylsulfonyl group and the like, and each is selected within the range of the designated number of carbon atoms.

The notation of C _a -C _b alkylamino in the present specification represents an amino group in which one of the hydrogen atoms is substituted with an alkyl group having the above-mentioned meaning consisting of _a to _b carbon atoms, for example, a methylamino group , Ethylamino group, n-propylamino group, i-propylamino group, n-butylamino group, i-butylamino group, tert-butylamino group and the like. Selected by range.

In the present specification, the notation of di (C _a -C _b alkyl) amino has the above-mentioned meaning that the number of carbon atoms which may be the same or different from each other is ab. Represents an amino group substituted by an alkyl group, such as dimethylamino group, ethyl (methyl) amino group, diethylamino group, n-propyl (methyl) amino group, i-propyl (methyl) amino group, di (n-propyl) Specific examples include an amino group, a di (n-butyl) amino group, and the like, and each is selected within the range of the designated number of carbon atoms.

The notation of C _a -C _b alkylimino in the present specification represents an alkyl-N = group having the above-mentioned meaning consisting of _a to _b carbon atoms, for example, methylimino group, ethylimino group, n-propylimino group. Specific examples include i-propylimino group, n-butylimino group, i-butylimino group, s-butylimino group, and the like, and each is selected within the range of the number of carbon atoms designated.

The notation of C _a -C _b alkoxyimino in the present specification represents an alkoxy-N = group having the above-mentioned meaning consisting of _a to _b carbon atoms, for example, methoxyimino group, ethoxyimino group, n-propyl. Specific examples include an oxyimino group, an i-propyloxyimino group, an n-butyloxyimino group, and the like, and each is selected within the range of the designated number of carbon atoms.

The notation of C _a -C _b alkylcarbonyl in the present specification represents an alkyl-C (O) -group having the above-mentioned meaning consisting of _a to _b carbon atoms, for example, acetyl group, propionyl group, butyryl group. , Isobutyryl group, valeryl group, isovaleryl group, 2-methylbutanoyl group, pivaloyl group, hexanoyl group, heptanoyl group, and the like, and specific examples thereof are selected within the range of the number of carbon atoms designated.

The notation of C _a -C _b haloalkylcarbonyl in the present specification represents a haloalkyl-C (O) -group having the above-mentioned meaning consisting of _a to _b carbon atoms, such as a fluoroacetyl group, a chloroacetyl group, Difluoroacetyl group, dichloroacetyl group, trifluoroacetyl group, chlorodifluoroacetyl group, bromodifluoroacetyl group, trichloroacetyl group, pentafluoropropionyl group, heptafluorobutanoyl group, 3-chloro-2,2-dimethylpropanoyl group Etc. are given as specific examples, and each is selected within the range of the designated number of carbon atoms.

The notation of C _a -C _b cycloalkylcarbonyl in the present specification represents a cycloalkyl-C (O) -group having the above-mentioned meaning consisting of _a to _b carbon atoms, such as cyclopropylcarbonyl group, 2 Specific examples include -methylcyclopropylcarbonyl group, cyclobutylcarbonyl 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 halocycloalkylcarbonyl represents a halocycloalkyl-C (O) — group having the above-mentioned meaning consisting of _a to _b carbon atoms. Specific examples include a dichlorocyclopropylcarbonyl group, a 2,2-dichloro-1-methylcyclopropylcarbonyl group, and the like, which are selected in the range of the designated number of carbon atoms.

The notation of C _a -C _b alkoxycarbonyl in the present specification represents an alkyl-O—C (O) — group having the above-mentioned meaning consisting of _a to _b carbon atoms, for example, methoxycarbonyl group, ethoxycarbonyl Group, n-propyloxycarbonyl group, i-propyloxycarbonyl group, n-butoxycarbonyl group, i-butoxycarbonyl group, tert-butoxycarbonyl group and the like, and specific ranges of the number of carbon atoms are designated. Selected.

The notation of C _a -C _b haloalkoxycarbonyl in the present specification represents a haloalkyl-O—C (O) — group having the above-mentioned meaning consisting of _a to _b carbon atoms, such as a chloromethoxycarbonyl group, Specific examples include 2-chloroethoxycarbonyl group, 2,2-difluoroethoxycarbonyl group, 2,2,2-trifluoroethoxycarbonyl group, 2,2,2-trichloroethoxycarbonyl group, and the like. Selected in the range of the number of carbon atoms.

The notation of C _a -C _b alkylaminocarbonyl in the present specification represents a carbamoyl group in which one of the hydrogen atoms is substituted with an alkyl group having the above-mentioned meaning consisting of _a to _b carbon atoms, for example, methylcarbamoyl Group, ethylcarbamoyl group, n-propylcarbamoyl group, i-propylcarbamoyl group, n-butylcarbamoyl group, i-butylcarbamoyl group, s-butylcarbamoyl group, tert-butylcarbamoyl group, etc. Is selected within the range of the specified number of carbon atoms.

In the present specification, the expression C _a -C _b haloalkylaminocarbonyl represents a carbamoyl group in which one of the hydrogen atoms is substituted with a haloalkyl group having the above-described meaning consisting of _a to _b carbon atoms, for example, 2-fluoro Specific examples include ethylcarbamoyl group, 2-chloroethylcarbamoyl group, 2,2-difluoroethylcarbamoyl group, 2,2,2-trifluoroethylcarbamoyl group, etc. Is done.

In the present specification, the notation of di (C _a -C _b alkyl) aminocarbonyl means in the above meaning that the number of carbon atoms which may be the same or different from each other is _a to _b. Represents a carbamoyl group substituted by an alkyl group, such as N, N-dimethylcarbamoyl group, N-ethyl-N-methylcarbamoyl group, N, N-diethylcarbamoyl group, N, N-di (n-propyl) carbamoyl Specific examples include a group, an N, N-di (n-butyl) carbamoyl group, and the like, and each is selected within the range of the designated number of carbon atoms.

In the present specification, C _a -C _b alkylaminosulfonyl represents a sulfamoyl group in which one of the hydrogen atoms is substituted with an alkyl group having the above-mentioned meaning consisting of _a to _b carbon atoms. Famoyl group, ethylsulfamoyl group, n-propylsulfamoyl group, i-propylsulfamoyl group, n-butylsulfamoyl group, i-butylsulfamoyl group, s-butylsulfamoyl group, Specific examples include a tert-butylsulfamoyl group and the like, and each is selected within the range of the designated number of carbon atoms.

The notation of C _a -C _b alkoxy (C _d -C _e ) alkyl in the present specification indicates that a hydrogen atom bonded to a carbon atom is substituted by any C _a -C _b alkoxy group having the aforementioned meaning, respectively. It represents an alkyl group having the above-mentioned meaning consisting of de to e carbon atoms, and is selected in the range of each designated number of carbon atoms.

In the present specification, C _a -C _b allenyl is a straight or branched chain consisting of _a to _b carbon atoms, and two double bonds between three carbons in the molecule. Represents an unsaturated hydrocarbon group having a continuous partial structure of -C = C = C-, for example, propadienyl group, 1,2-butadienyl group, 1,2-pentadienyl group, 3-methyl-1,2-butadienyl Groups and the like are listed as specific examples, and each group is selected within the range of the designated number of carbon atoms.

The notation of C _a -C _b alkenylsulfinyl in the present specification represents an alkenyl-S (O) -group having the above-mentioned meaning consisting of _a to _b carbon atoms, and ranges of each designated number of carbon atoms. Selected.

Optionally substituted by ^{R 5} in this specification _(C a _{~C b)} ^alkyl, optionally substituted by ^{R 5a} _(C ^a _{~C b)} ^alkyl, optionally substituted by ^{R 14} _(C a ~ C _b) ^alkyl, optionally substituted by ^{R 14a} _(C ^{a ~C} _b) ^alkyl, optionally substituted by ^{R 19} _(C a ^~C _b) ^alkyl, optionally substituted by ^{R 23} _{(C a} ~ C _b ) alkyl or (C _a -C _b ) alkyl optionally substituted by R ^{28 is represented} by any R ⁵ , R ^5a , R ¹⁴ , R ^14a , R ¹⁹ , R ²³ or R ²⁸ . Represents an alkyl group having the above-mentioned meaning, wherein the number of carbon atoms is optionally substituted with hydrogen atoms bonded to carbon atoms, and is selected in the range of each designated number of carbon atoms. At this time, when two or more substituents R ⁵ , R ^5a , R ¹⁴ , R ^14a , R ¹⁹ , R ²³ or R ²⁸ on each (C _a -C _b ) alkyl group are present, each R ⁵ , R ^5a , R ¹⁴ , R ^14a , R ¹⁹ , R ²³ or R ²⁸ may be the same as or different from each other.

Optionally substituted by ^{R 5} in this specification _(C a _{~C b)} ^cycloalkyl, optionally substituted by ^{R 5a} _(C ^a _{~C b)} ^cycloalkyl, optionally substituted by ^{R 14} (C _a- C _b ) cycloalkyl, optionally substituted by R ^14a (C _a -C _b ) cycloalkyl, optionally substituted by R ¹⁸ (C _a -C _b ) cycloalkyl, optionally substituted by R ¹⁹ been _(C a _{~C b)} ^cycloalkyl, notation such as _(C a _{~C b)} cycloalkyl optionally substituted by optionally substituted _(C a _{~C b)} cycloalkyl or ^{R 28} by ^{R 23} can be any ^{R 5, R 5a, R 14} , R 14a, by ^{R 18, R} 19, ^{R 23} or ^{R 28,} an optionally substituted hydrogen atoms bonded to carbon atoms A cycloalkyl group is defined above in which the number of carbon atoms is made of a~b number is selected from the range of the specified number of carbon atoms. At this time, when two or more substituents R ⁵ , R ^5a , R ¹⁴ , R ^14a , R ¹⁸ , R ¹⁹ , R ²³ or R ²⁸ on each (C _a -C _b ) cycloalkyl group are present, Each R ⁵ , R ^5a , R ¹⁴ , R ^14a , R ¹⁸ , R ¹⁹ , R ²³ or R ²⁸ may be the same or different from each other, and the substitution position may be a ring structure portion or a side chain portion. Or both.

Optionally substituted by ^{R 5} in this specification _(C a _{~C b)} ^alkenyl, optionally substituted by ^{R 5a} _(C ^a _{~C b)} ^alkenyl, optionally substituted by ^{R 14} _(C a ~ C _b) ^alkenyl, optionally substituted by ^{R 14a} _(C ^{a ~C} _b) ^alkenyl, optionally substituted by ^{R 19} _(C a ^~C _b) ^alkenyl, optionally substituted by ^{R 23} _{(C a} ~ C _b ) alkenyl or (C _a -C _b ) alkenyl optionally substituted by R ²⁸ may be represented by any R ⁵ , R ^5a , R ¹⁴ , R ^14a , R ¹⁹ , R ²³ or R ²⁸ . Represents an alkenyl group having the above-mentioned meaning, wherein the number of carbon atoms is optionally substituted with hydrogen atoms bonded to carbon atoms, and is selected within the range of each designated number of carbon atoms. It is. At this time, when two or more substituents R ⁵ , R ^5a , R ¹⁴ , R ^14a , R ¹⁹ , R ²³ or R ²⁸ on each (C _a -C _b ) alkenyl group are present, each R ⁵ , R ^5a , R ¹⁴ , R ^14a , R ¹⁹ , R ²³ or R ²⁸ may be the same as or different from each other.

The ^{R 5} herein optionally substituted _(C a _{~C b)} ^{cycloalkenyl,} optionally substituted by ^{R 5a} _(C ^a _{~C b)} ^{cycloalkenyl,} optionally substituted by ^{R 14} (C _a- C _b ) cycloalkenyl, optionally substituted by R ^14a (C _a -C _b ) cycloalkenyl, optionally substituted by R ¹⁸ (C _a -C _b ) cycloalkenyl, optionally substituted by R ¹⁹ It has been _(C a _{~C b)} optionally substituted by cycloalkenyl or ^{R 23} _(C a _{~C b)} optionally substituted by cycloalkenyl or ^{R 28} _(C a _{~C b)} representation of such cycloalkenyl can be any ^{R 5, R 5a, R 14} , R 14a, by ^{R 18, R} 19, ^{R 23} or ^{R 28,} hydrogen atoms bonded to carbon atoms Is optionally substituted carbon atoms represents a cycloalkenyl group which is the meaning of consisting a~b number is selected from the range of the specified number of carbon atoms. At this time, when two or more substituents R ⁵ , R ^5a , R ¹⁴ , R ^14a , R ¹⁸ , R ¹⁹ , R ²³ or R ²⁸ on each (C _a -C _b ) cycloalkenyl group are present, Each R ⁵ , R ^5a , R ¹⁴ , R ^14a , R ¹⁸ , R ¹⁹ , R ²³ or R ²⁸ may be the same or different from each other, and the substitution position may be a ring structure portion or a side chain portion. Or both.

Optionally substituted by ^{R 5} in this specification _(C a _{~C b)} ^alkynyl, optionally substituted by ^{R 5a} _(C ^a _{~C b)} ^alkynyl, optionally substituted by ^{R 14} _(C a ~ C _b ) alkynyl, optionally substituted by R ^14a (C _a -C _b ) alkynyl, optionally substituted by R ¹⁹ (C _a -C _b ) alkynyl or optionally substituted by R ²³ (C _a -C _b) alkynyl or optionally substituted by ^{R 28} _(C a ~C _b) notation alkynyl or the like, any of ^{R 5, R 5a, R 14} , R 14a, by R ^{19, R 23} or ^{R 28} Represents an alkynyl group as defined above, wherein the number of carbon atoms is optionally substituted with hydrogen atoms bonded to carbon atoms, and is selected within the range of each specified number of carbon atoms. It is. At this time, when two or more substituents R ⁵ , R ^5a , R ¹⁴ , R ^14a , R ¹⁹ , R ²³ or R ²⁸ on each (C _a -C _b ) alkynyl group are present, each R ⁵ , R ^5a , R ¹⁴ , R ^14a , R ¹⁹ , R ²³ or R ²⁸ may be the same as or different from each other.

In the present specification, [R ⁸ forms a C _{2 to} C ₇ alkylene chain together with R ^8a to form a 3- to 8-membered ring together with the nitrogen atom to which R ⁸ and R ^8a are bonded. The alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom,
[R ¹³ represents that, together with R ^13a , a C _{2 to} C ₇ alkylene chain is formed to form a 3- to 8-membered ring together with the nitrogen atom to which R ¹³ and R ^13a are bonded. At this time, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom.]
[R ¹⁷ represents that, together with R ^17a , a C _{2 to} C ₇ alkylene chain may be formed to form a 3- to 8-membered ring together with the nitrogen atom to which R ¹⁷ and R ^17a are bonded. At this time, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom.]
Specific examples of notation such as aziridine, azetidine, azetidin-2-one, pyrrolidine, pyrrolidin-2-one, oxazolidine, oxazolidine-2-one, oxazolidine-2-thione, thiazolidine, thiazolidine-2-one, thiazolidine -2-thione, imidazolidine, imidazolidine-2-one, imidazolidine-2-thione, piperidine, piperidin-2-one, piperidine-2-thione, 2H-3,4,5,6-tetrahydro-1, 3-Oxazin-2-one, 2H-3,4,5,6-tetrahydro-1,3-oxazine-2-thione, morpholine, 2H-3,4,5,6-tetrahydro-1,3-thiazine- 2-one, 2H-3,4,5,6-tetrahydro-1,3-thiazine-2-thione, thiomorpholine, pe Tetrahydropyrimidine-2-one, piperazine, homopiperidine, homopiperidine-2-one, heptamethyleneimine, and the like, may be selected from the range of the number of each of the specified atoms.

In the present specification, [R ^8c and R ^8d are combined together to form a C _{4 to} C ₆ alkylene chain or a C _{4 to} C ₆ alkenylene chain, whereby 5 to 7 together with the carbon atom to which R ^8c and R ^8d are bonded. Represents that a member ring may be formed, and at this time, the alkylene chain or alkenylene chain may contain 1 to 3 oxygen atoms, sulfur atoms or nitrogen atoms.]
Specific examples of notation such as thiazolidine-2-ylidene, 2,3-dihydrothiazol-2-ylidene, imidazolidine-2-ylidene, 2,3-dihydroimidazol-2-ylidene, 2,3-dihydro- 1,3,4-thiadiazole-2-ylidene, 1,2-dihydropyridin-2-ylidene, 2,3-dihydropyridazine-3-ylidene, 1,2-dihydropyrazin-2-ylidene, 1,2-dihydropyrimidine -2-ylidene, 6H-2,3-dihydro-1,3,4-thiadiazin-2-ylidene, and the like are listed, and each is selected in the range of the specified number of atoms.

In the present specification, [R ^8e and R ^8f are combined together to form a C _{4 to} C ₆ alkylene chain or a C _{4 to} C ₆ alkenylene chain, whereby 5 to 7 together with the sulfur atom to which R ^8e and R ^8f are bonded. Represents that a member ring may be formed, and at this time, the alkylene chain or alkenylene chain may contain 1 to 3 oxygen atoms, sulfur atoms or nitrogen atoms.]
Specific examples of the notation include tetrahydrothiophene, tetrahydrothiophenone, tetrahydrothiopyran, thiopyran-4-one, 1,4-thioxan, and the like, and are selected in the range of the designated number of atoms.

In the pyrazole derivative represented by the general formula (1), which is an active ingredient of the parasite control agent of the present invention, examples of the range of the substituent represented by R ³ include the following groups.

^{That, R} 3 I: a hydrogen atom, a halogen _atom, C 1 -C ₆ alkyl.

R ³ II: a halogen atom, C ₁ -C ₆ alkyl.

R ³ III: a halogen atom.

R ³ _IV: C 1 ~C ₆ alkyl.

R ³ V: a hydrogen atom.

In the pyrazole derivative represented by the general formula (1), which is an active ingredient of the antiparasitic agent of the present invention, examples of the range of the substituent represented by A ² include the following groups.

^{That, A 2 I: D1-14, D1-15} , D1-16, D1-17, D1-31, D1-34, D1-35, D1-52, D1-57, D1-68.

^{A 2 II: D1-15, D1-16,} D1-17.

^{A 2 III: D1-14, D1-31,} D1-34, D1-35, D1-52, D1-57.

A ² IV: D1-14.

A ² V: D1-17.

In the pyrazole derivative represented by the general formula (1), which is an active ingredient of the parasite control agent of the present invention, examples of the range of the substituent represented by X ¹ include the following groups.

X ¹ I: optionally substituted with ^{R 5} _(C 1 ~C ₆₎ alkyl [wherein, ^{R 5} represents _{^{-S (O) r R 11,}} R 11 is _C 1 -C ₆ alkyl or _{C 1} -C ₆ haloalkyl, r is an integer of 0 to 2. ], D2-37.

X ¹ II: optionally substituted with ^{R 5} _(C 1 ~C ₆₎ alkyl [wherein, ^{R 5} represents _{^{-S (O) r R 11,}} R 11 is _C 1 -C ₆ alkyl or _{C 1} -C ₆ haloalkyl, r is an integer of 0 to 2. ].

X ¹ III: optionally substituted with ^{R 5} _(C 1 ^~C ₆₎ alkyl [wherein, ^{R 5} represents a halogen atom. ].

X ¹ IV: D2-37.

In the pyrazole derivative represented by the general formula (1), which is an active ingredient of the parasite control agent of the present invention, examples of the range of the substituent represented by X ^1a include the following groups.

X ^1a I: a hydrogen _atom, C 1 -C ₆ ^alkyl, optionally substituted _(C 1 ~C ₆₎ alkyl [where in ^{R 5a, R 5a} represents a halogen ^{_{atom, -S (O) r R 11}} , - S ⁽⁼ NR ^{13b) R 11a,} or -S ^(O) represent ^{(= NR 13b) R 11a,} R 11 represents a _C 1 -C ₆ alkyl or _C 1 -C ₆ haloalkyl, r is integer of 0 to 2 R ^11a represents C ₁ -C ₆ alkyl and R ^13b represents cyano. ], D2-37.

X ^{1a II:} optionally substituted with ^{R 5a} _(C 1 ~C ₆₎ alkyl ^{[wherein, R 5a} represents _{^{-S (O) r R 11,}} R 11 is _C 1 -C ₆ alkyl or _{C 1} -C ₆ haloalkyl, r is an integer of 0 to 2. ].

X ^{1a III:} optionally substituted with ^{R 5a} _(C 1 ^~C ₆₎ alkyl ^{[wherein, R 5a} represents a halogen atom. ].

X ^{1a IV:} optionally substituted with ^{R 5a} _(C 1 ^~C ₆₎ alkyl ^{[wherein, R 5a} is ^{-S (=} NR ^{13b) R 11a,} or -S ^(O) a ⁽⁼ NR ^{13b) R 11a} R ^11a represents C ₁ -C ₆ alkyl and R ^13b represents cyano. ].

X ^1a V: D2-37.

X ^1a VI: C ₁ -C ₆ alkyl.

X ^{1a VII:} optionally substituted with ^{R 5a} _(C 1 ~C ₆₎ alkyl ^{[wherein, R 5a} represents ^{-C (R 12) = NOR 11} , R 11 is _C 1 -C ₆ alkyl or C _{1 to} C ₆ haloalkyl is represented, and R ¹² represents C _{1 to} C ₆ alkyl. ].

  In the pyrazole derivative represented by the general formula (1), which is an active ingredient of the parasite control agent of the present invention, examples of the range of the substituent represented by B include the following groups.

BI: B-1 to B-6 [wherein A ³ represents —O—, —S (O) _r —, —C (X ^1b ) X ^1c —, and X ^1b and X ^1c each independently represent Represents a hydrogen atom or C ₁ -C ₆ alkyl, X ^1d and X ^1f represent a hydrogen atom, n represents an integer of 1, and r represents an integer of 0 to 2. ].

BII: B-1, B- 2, B-4, B-5 [ ^wherein, A 3 is _{-O -, - S (O)} r -, - C (X 1b) X 1c - ^{represents, X 1b} And X ^1c each independently represents a hydrogen atom or C ₁ -C ₆ alkyl, X ^1d and X ^1f represent a hydrogen atom, n represents an integer of 1, and r represents an integer of 0 to 2. ].

BIII: B-3, B-6 [wherein A ³ represents —O—, —S (O) _r —, —C (X ^1b ) X ^1c —, and X ^1b and X ^1c each independently represent Represents a hydrogen atom or C ₁ -C ₆ alkyl, X ^1d and X ^1f represent a hydrogen atom, n represents an integer of 1, and r represents an integer of 0 to 2. ].

BIV: B-1 and B-3 [wherein A ³ represents —O—, —S (O) _r —, —C (X ^1b ) X ^1c —, and X ^1b and X ^1c each independently represent Represents a hydrogen atom or C ₁ -C ₆ alkyl, X ^1d and X ^1f represent a hydrogen atom, n represents an integer of 1, and r represents an integer of 0 to 2. ].

BV: B-1 [wherein A ³ represents —C (X ^1b ) X ^1c —, X ^1b and X ^1c each independently represent a hydrogen atom or C ₁ -C ₆ alkyl, and X ^1d and X ^1f represents a hydrogen atom, and n represents an integer of 1. ].

BVI: B-3 [wherein A ³ represents —C (X ^1b ) X ^1c —, X ^1b and X ^1c each independently represent a hydrogen atom or C ₁ -C ₆ alkyl, and X ^1d and X ^1f represents a hydrogen atom, and n represents an integer of 1. ].

BVII: B-4 [wherein A ³ represents —CH ₂ —, and n represents an integer of 1. ].

BVIII: B-1 [wherein A ³ represents —O—, X ^1d and X ^1f represent a hydrogen atom, and n represents an integer of 1. ].

BIX: B-3 [where A ³ represents —O—, X ^1d and X ^1f represent a hydrogen atom, and n represents an integer of 1. ].

BX: B-1 [wherein A ³ represents —S (O) _r —, X ^1d and X ^1f represent a hydrogen atom, n represents an integer of 1, and r represents an integer of 0 to 2] . ].

BXI: B-3 [wherein A ³ represents —S (O) _r —, X ^1d and X ^1f represent a hydrogen atom, n represents an integer of 1, and r represents an integer of 0 to 2. ].

Each group which shows the range of each substituent in the pyrazole derivative represented by the general formula (1) which is an active ingredient of these parasite control agents of the present invention can be arbitrarily combined, and each range of the pyrazole derivative. Represents. Examples of combinations of R ³ , A ² , X ¹ and X ^1a include, for example, combinations shown in Table 1 below. Examples of combinations of R ³ , B, X ¹ and X ^1a include the combinations shown in Table 2 below. However, the combinations of Tables 1 and 2 are for illustrative purposes, and the present invention is not limited to these.
[Table 1] [Table 1] (continued)
―――――――――――――― ――――――――――――――
R ³ A ² X ¹ X ^1a R ³ A ² X ¹ X ^1a
―――――――――――――― ――――――――――――――
R ³ IA ² IX ¹ IX ^1a IR ³ II A ² VX ¹ II X ^1a IV
R ³ IA ² II X ¹ II X ^1a IR ³ II A ² VX ¹ II X ^1a V
R ³ IA ² II X ¹ II X ^1a II R ³ II A ² VX ¹ II X ^1a VI
R ³ IA ² II X ¹ II X ^1a III R ³ III A ² IX ¹ IX ^1a I
R ³ IA ² II X ¹ II X ^1a IV R ³ III A ² II X ¹ II X ^1a I
R ³ IA ² II X ¹ II X ^1a VR ³ III A ² II X ¹ II X ^1a II
R ³ IA ² II X ¹ II X ^1a VI R ³ III A ² II X ¹ II X ^1a III
R ³ IA ² II --- X ^1a II R ³ III A ² II X ¹ II X ^1a IV
R ³ IA ² II --- X ^1a IV R ³ III A ² II X ¹ II X ^1a V
R ³ IA ² II --- X ^1a VII R ³ III A ² II X ¹ II X ^1a VI
R ³ IA ² III X ¹ II --- R ³ III A ² II --- X ^1a II
R ³ IA ² IV X ¹ II --- R ³ III A ² II --- X ^1a IV
R ³ IA ² VX ¹ II X ^1a IR ³ III A ² II --- X ^1a VII
R ³ IA ² VX ¹ II X ^1a II R ³ III A ² III X ¹ II ---
R ³ IA ² VX ¹ II X ^1a III R ³ III A ² IV X ¹ II ---
R ³ IA ² VX ¹ II X ^1a IV R ³ III A ² VX ¹ II X ^1a I
R ³ IA ² VX ¹ II X ^1a VR ³ III A ² VX ¹ II X ^1a II
R ³ IA ² VX ¹ II X ^1a VI R ³ III A ² VX ¹ II X ^1a III
R ³ II A ² IX ¹ IX ^1a IR ³ III A ² VX ¹ II X ^1a IV
R ³ II A ² II X ¹ II X ^1a IR ³ III A ² VX ¹ II X ^1a V
R ³ II A ² II X ¹ II X ^1a II R ³ III A ² VX ¹ II X ^1a VI
R ³ II A ² II X ¹ II X ^1a III R ³ IV A ² IX ¹ IX ^1a I
R ³ II A ² II X ¹ II X ^1a IV R ³ IV A ² II X ¹ II X ^1a I
R ³ II A ² II X ¹ II X ^1a VR ³ IV A ² II X ¹ II X ^1a II
R ³ II A ² II X ¹ II X ^1a VI R ³ IV A ² II X ¹ II X ^1a III
R ³ II A ² II --- X ^1a II R ³ IV A ² II X ¹ II X ^1a IV
―――――――――――――― ――――――――――――――
[Table 1] (continued) [Table 1] (continued)
―――――――――――――― ――――――――――――――
R ³ A ² X ¹ X ^1a R ³ A ² X ¹ X ^1a
―――――――――――――― ――――――――――――――
R ³ II A ² II --- X ^1a IV R ³ IV A ² II X ¹ II X ^1a V
R ³ II A ² II --- X ^1a VII R ³ IV A ² II X ¹ II X ^1a VI
R ³ II A ² III X ¹ II --- R ³ IV A ² II --- X ^1a II
R ³ II A ² IV X ¹ II --- R ³ IV A ² II --- X ^1a IV
R ³ II A ² VX ¹ II X ^1a IR ³ IV A ² II --- X ^1a VII
R ³ II A ² VX ¹ II X ^1a II R ³ IV A ² III X ¹ II ---
R ³ IV A ² III X ¹ II --- R ³ IV A ² IV X ¹ II ---
R ³ II A ² VX ¹ II X ^1a III R ³ VA ² II X ¹ II X ^1a VI
R ³ IV A ² VX ¹ II X ^1a IR ³ VA ² II --- X ^1a II
R ³ IV A ² VX ¹ II X ^1a II R ³ VA ² II --- X ^1a IV
R ³ IV A ² VX ¹ II X ^1a III R ³ VA ² II --- X ^1a VII
R ³ IV A ² VX ¹ II X ^1a IV R ³ VA ² IV X ¹ II ---
R ³ VA ² III X ¹ II --- R ³ VA ² VX ¹ II X ^1a I
R ³ IV A ² VX ¹ II X ^1a VR ³ VA ² VX ¹ II X ^1a II
R ³ IV A ² VX ¹ II X ^1a VI R ³ VA ² VX ¹ II X ^1a III
R ³ VA ² IX ¹ IX ^1a IR ³ VA ² VX ¹ II X ^1a IV
R ³ VA ² II X ¹ II X ^1a IR ³ VA ² VX ¹ II X ^1a V
R ³ VA ² II X ¹ II X ^1a II R ³ VA ² VX ¹ II X ^1a VI
R ³ VA ² II X ¹ II X ^1a III ――――――――――――――
R ³ VA ² II X ¹ II X ^1a IV
R ³ VA ² II X ¹ II X ^1a V
――――――――――――――
[Table 2] [Table 2] (continued)
―――――――――――― ――――――――――――
BX ¹ X ^1a BX ¹ X ^1a
―――――――――――― ――――――――――――
BI X ¹ IX ^1a I BIII X ¹ III ---
BI X ¹ IX ^1a II BIII X ¹ IV ---
BI X ¹ IX ^1a III BIV X ¹ IX ^1a I
BI X ¹ IX ^1a IV BIV X ¹ IX ^1a II
BI X ¹ IX ^1a V BIV X ¹ IX ^1a III
BI X ¹ IX ^1a VI BIV X ¹ IX ^1a IV
BI X ¹ II X ^1a I BIV X ¹ IX ^1a V
BI X ¹ II X ^1a II BIV X ¹ IX ^1a VI
BI X ¹ II X ^1a III BIV X ¹ II X ^1a I
BI X ¹ II X ^1a IV BIV X ¹ II X ^1a II
BI X ¹ II X ^1a V BIV X ¹ II X ^1a III
BI X ¹ II X ^1a VI BIV X ¹ II X ^1a IV
BI X ¹ III X ^1a I BIV X ¹ II X ^1a V
BI X ¹ III X ^1a II BIV X ¹ II X ^1a VI
BI X ¹ III X ^1a III BIV X ¹ III X ^1a I
BI X ¹ III X ^1a IV BIV X ¹ III X ^1a II
BI X ¹ III X ^1a V BIV X ¹ III X ^1a III
BI X ¹ III X ^1a VI BIV X ¹ III X ^1a IV
BI X ¹ IV X ^1a I BIV X ¹ III X ^1a V
BI X ¹ IV X ^1a II BIV X ¹ III X ^1a VI
BI X ¹ IV X ^1a III BIV X ¹ IV X ^1a I
BI X ¹ IV X ^1a IV BIV X ¹ IV X ^1a II
BI X ¹ IV X ^1a V BIV X ¹ IV X ^1a III
BI X ¹ IV X ^1a VI BIV X ¹ IV X ^1a IV
BII --- X ^1a I BIV X ¹ IV X ^1a V
―――――――――――― ――――――――――――
[Table 2] (continued) [Table 2] (continued)
―――――――――――― ――――――――――――
BX ¹ X ^1a BX ¹ X ^1a
―――――――――――― ――――――――――――
BII --- X ^1a II BIV X ¹ IV X ^1a VI
BII --- X ^1a III BV --- X ^1a I
BII --- X ^1a IV BV --- X ^1a II
BII --- X ^1a V BV --- X ^1a III
BII --- X ^1a VI BV --- X ^1a IV
BIII X ¹ I --- BV --- X ^1a V
BIII X ¹ II --- BV --- X ^1a VI
BVI X ¹ I --- BIX X ¹ I ---
BVI X ¹ II --- BIX X ¹ II ---
BVI X ¹ III --- BIX X ¹ III ---
BVI X ¹ IV --- BIX X ¹ IV ---
BVII --- X ^1a I BX --- X ^1a I
BVII --- X ^1a II BX --- X ^1a II
BVII --- X ^1a III BX --- X ^1a III
BVII --- X ^1a IV BX --- X ^1a IV
BVII --- X ^1a V BX --- X ^1a V
BVII --- X ^1a VI BX --- X ^1a VI
BVIII --- X ^1a I BXI X ¹ I ---
BVIII --- X ^1a II BXI X ¹ II ---
BVIII --- X ^1a III BXI X ¹ III ---
BVIII --- X ^1a IV BXI X ¹ IV ---
BVIII --- X ^1a V ――――――――――――
BVIII --- X ^1a VI
――――――――――――
The pyrazole derivative represented by the general formula (1), which is an active ingredient of the parasite control agent of the present invention, can be produced by the following method.

  Manufacturing method A

The general formula (2-1) [wherein ^{A 1, R 2, R 3} , R 4 and n1 represent the same meanings as described above. ] And a compound represented _by, by reacting NH 2 _{NH 2,} the general formula (2-2) [wherein ^{A 1, R 2, R 3} , R 4 and n1 are as defined above. ] Can be synthesized.

In this reaction, NH ₂ NH ₂ can be used in a range of 0.5 to 50 equivalents relative to 1 equivalent of the compound represented by General Formula (2-1).

  If necessary, an acid such as hydrochloric acid, sulfuric acid or p-toluenesulfonic acid, or a base such as potassium carbonate, triethylamine, pyridine or 4- (dimethylamino) pyridine can be used.

  This reaction can be carried out without solvent, but a solvent may be used. For example, polar solvent such as N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolinone, water, methanol, ethanol, propanol, 2-propanol, ethylene glycol Alcohols such as diethyl ether, tetrahydrofuran and diphenyl ether, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, pentane and n-hexane And aliphatic hydrocarbons. These solvents may be used alone or as a mixture of two or more thereof.

  The reaction temperature can be set to any temperature from −60 ° C. to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually arbitrary in the range of 5 minutes to 100 hours. Can be set.

The compound represented by the general formula (2-2) thus obtained and the general formula (8) [wherein X ^1a represents the same meaning as described above, and J ^a represents ^a halogen atom, —OH, —OSO. ₂ Me, a leaving group such as —OSO ₂ CF ₃ . By reacting a compound represented by the general formula (3), A ¹ , R ² , R ³ , R ⁴ , X ^1a and n1 have the same meaning as described above. ] And general formula (4) [wherein A ¹ , R ² , R ³ , R ⁴ , X ^1a and n1 represent the same meaning as described above.] ] The pyrazole derivative represented by this can be obtained.

  Some of the compounds represented by the general formula (8) are known compounds, and some of them are commercially available. Others can be easily synthesized according to known methods described in the literature.

  This reaction can be carried out without solvent, but a solvent may be used. For example, polar solvent such as N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolinone, water, methanol, ethanol, propanol, 2-propanol, ethylene glycol Alcohols such as diethyl ether, tetrahydrofuran and diphenyl ether, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, pentane and n-hexane And aliphatic hydrocarbons. These solvents may be used alone or as a mixture of two or more thereof.

  The reaction temperature can be set to any temperature from −60 ° C. to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually arbitrary in the range of 5 minutes to 100 hours. Can be set.

  If necessary, bases such as hydrochloric acid, sulfuric acid, p-toluenesulfonic acid and the like, potassium carbonate, triethylamine, pyridine, 4- (dimethylamino) pyridine, sodium hydride, sodium hydroxide, potassium hydroxide, or Mitsunobu reaction using diethyl azodicarboxylate and triphenylphosphine or the like can be used.

In addition, the compound represented by the general formula (2-1) and a known general formula (6) [wherein X ^1a represents the same meaning as described above. ] The pyrazole derivative represented by General formula (3) and General formula (4) is also compoundable by making the compound represented by these react.

  In this reaction, the compound represented by the general formula (6) can be used in the range of 0.5 to 50 equivalents with respect to 1 equivalent of the compound represented by the general formula (2-1).

  If necessary, an acid such as hydrochloric acid, sulfuric acid or p-toluenesulfonic acid, or a base such as potassium carbonate, triethylamine, pyridine or 4- (dimethylamino) pyridine can be used.

  This reaction can be carried out without solvent, but a solvent may be used. For example, polar solvent such as N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolinone, water, methanol, ethanol, propanol, 2-propanol, ethylene glycol Alcohols such as diethyl ether, tetrahydrofuran and diphenyl ether, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, pentane and n-hexane And aliphatic hydrocarbons. These solvents may be used alone or as a mixture of two or more thereof.

  The reaction temperature can be set to any temperature from −60 ° C. to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually arbitrary in the range of 5 minutes to 100 hours. Can be set.

In addition, the compound represented by the general formula (2-1) and a known general formula (7) [wherein X ¹ represents the same meaning as described above. ] Is reacted with the compound represented by general formula (5) [wherein A ¹ , R ² , R ³ , R ⁴ , X ¹ and n1 have the same meaning as described above. ] Can be synthesized.

  In this reaction, the compound represented by the general formula (7) can be used in the range of 0.5 to 50 equivalents with respect to 1 equivalent of the compound represented by the general formula (2-1).

  If necessary, an acid such as hydrochloric acid, sulfuric acid or p-toluenesulfonic acid, or a base such as potassium carbonate, triethylamine, pyridine or 4- (dimethylamino) pyridine can be used.

  This reaction can be carried out without solvent, and a solvent may be used. For example, polar solvent such as N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolinone, water, methanol, ethanol, propanol, 2-propanol, ethylene glycol Alcohols such as diethyl ether, tetrahydrofuran and diphenyl ether, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, pentane and n-hexane And aliphatic hydrocarbons. These solvents may be used alone or in combination of two or more of them.

  The reaction temperature can be set to any temperature from −60 ° C. to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually arbitrary in the range of 5 minutes to 100 hours. Can be set.

  Manufacturing method B

General formula (17) [wherein A ¹ , R ² , R ³ , R ⁴ and n1 represent the same meaning as described above, and J ^b is a leaving group such as a halogen atom, —OSO ₂ Me, —OSO ₂ CF _3, etc. Represents. And a compound represented by the general formula (11), wherein A ² represents the same meaning as described above. ] Is reacted in the presence of a catalyst and a base, whereby the general formula (9) [wherein A ¹ , A ² , R ² , R ³ , R ⁴ and n1 have the same meaning as described above]. ] Can be synthesized.

  The amount of the compound represented by the general formula (11) can be used in the range of 0.8 to 5 equivalents relative to 1 equivalent of the compound represented by the general formula (17).

  Some of the compounds represented by the general formula (11) used here are known compounds, and some of them are available as commercial products. Others can be easily synthesized according to the methods described in the literature.

  Examples of the catalyst that can be used in this reaction include palladium catalysts such as palladium-carbon, palladium chloride, palladium acetate, bis (triphenylphosphine) palladium dichloride, tetrakis (triphenylphosphine) palladium, copper metal, copper acetate (monovalent). ), Copper acetate (divalent), copper oxide (monovalent), copper oxide (divalent), copper iodide and the like. The catalyst is used in an amount of 0.001 to 1.0 equivalent, preferably 0.01 to 0.5 equivalent, more preferably 0.05 to 0, relative to 1 equivalent of the compound represented by the general formula (17). It can be used in the range of 2 equivalents.

  Examples of the base to be used include tertiary amine compounds such as pyridine, diisopropylethylamine, and triethylamine, and inorganic bases such as sodium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, and sodium bicarbonate. The usage-amount of a base can be used in 0.1-10.0 equivalent with respect to 1 equivalent of compounds represented by General formula (17).

  This reaction can be carried out without solvent, but a solvent may be used. For example, polar solvent such as N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolinone, water, methanol, ethanol, propanol, 2-propanol, ethylene glycol Alcohols such as diethyl ether, tetrahydrofuran and diphenyl ether, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, pentane and n-hexane And aliphatic hydrocarbons. These solvents may be used alone or as a mixture of two or more thereof.

  The reaction temperature can be set to any temperature from −60 ° C. to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually arbitrary in the range of 5 minutes to 100 hours. Can be set.

  Manufacturing method C

The general formula (12) [wherein ^{A 1, R 2, R 3} , R 4 and n1 represent the same meanings as defined ^{above, R 50} is a table a good _C 1 -C ₆ alkyl, hydrogen or the same or different Alternatively, two R ⁵⁰ may be taken together to form —CH ₂ CH ₂ — or —C (CH ₃ ) ₂ C (CH ₃ ) ₂ —. The compound represented by general formula (13) [wherein A ² and J ^b represent the same meaning as described above]. The pyrazole derivative represented by the general formula (9) can be synthesized by reacting with the compound represented by the formula (9) in the presence of a catalyst and a base.

  The compound represented by the general formula (13) can be used in a range of 0.8 to 5 equivalents with respect to 1 equivalent of the compound represented by the general formula (12).

  Examples of the catalyst that can be used in this reaction include palladium catalysts such as palladium-carbon, palladium chloride, palladium acetate, bis (triphenylphosphine) palladium dichloride, tetrakis (triphenylphosphine) palladium, copper metal, copper acetate (monovalent). ), Copper acetate (divalent), copper oxide (monovalent), copper oxide (divalent), copper iodide and the like. The usage-amount of a catalyst is 0.001-1.0 equivalent with respect to 1 equivalent of compounds represented by General formula (12), Preferably, it is 0.01-0.5 equivalent, More preferably, 0.05- The range is 0.2 equivalent.

  Examples of the base to be used include tertiary amine compounds such as pyridine, diisopropylethylamine, and triethylamine, and inorganic bases such as sodium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, and sodium bicarbonate. The usage-amount of a base is the range of 0.1-10.0 equivalent with respect to 1 equivalent of compounds represented by General formula (12).

  This reaction can be carried out without solvent, but a solvent may be used. For example, polar solvent such as N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolinone, water, methanol, ethanol, propanol, 2-propanol, ethylene glycol Alcohols such as diethyl ether, tetrahydrofuran and diphenyl ether, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, pentane and n-hexane And aliphatic hydrocarbons. These solvents may be used alone or as a mixture of two or more thereof.

  The reaction temperature can be set to any temperature from 0 ° C. to the reflux temperature of the solvent to be used, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but usually ranges from 5 minutes to 100 hours. Can be set.

  Manufacturing method D

General formula (20) [wherein A ¹ , R ² , R ⁴ and n1 represent the same meaning as described above, A ³ represents an oxygen atom, a sulfur atom, —C (R ^51a ) R ⁵¹ —, R ⁵¹ and R ^51a each independently represents a hydrogen atom or C _{1 to} C ₆ alkyl, and n represents an integer of 0 to 3. ] And a compound represented _by, by reacting NH 2 _{NH 2,} the general formula (21) [wherein ^{A 1, A 3, R 2} , R 4, n and n1 are as defined above. ] Can be synthesized.

In this reaction, NH ₂ NH ₂ can be used in a range of 0.5 to 50 equivalents relative to 1 equivalent of the compound represented by the general formula (20).

  If necessary, an acid such as hydrochloric acid, sulfuric acid or p-toluenesulfonic acid, or a base such as potassium carbonate, triethylamine, pyridine or 4- (dimethylamino) pyridine can be used.

  This reaction can be carried out without solvent, but a solvent may be used. For example, polar solvent such as N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolinone, water, methanol, ethanol, propanol, 2-propanol, ethylene glycol Alcohols such as diethyl ether, tetrahydrofuran and diphenyl ether, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, pentane and n-hexane And aliphatic hydrocarbons. These solvents may be used alone or as a mixture of two or more thereof.

  The reaction temperature can be set to any temperature from −60 ° C. to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually arbitrary in the range of 5 minutes to 100 hours. Can be set.

By reacting the compound represented by the general formula (21) thus obtained with the compound represented by the general formula (8), the general formula (22) [wherein A ¹ , A ³ , R ² , R ⁴ , X ^1a , n and n1 represent the same meaning as described above. ] And general formula (23) [wherein A ¹ , A ³ , R ² , R ⁴ , X ^1a , n and n1 represent the same meaning as described above.] ] The pyrazole derivative represented by this can be obtained.

  This reaction can be carried out without solvent, but a solvent may be used. For example, polar solvent such as N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolinone, water, methanol, ethanol, propanol, 2-propanol, ethylene glycol Alcohols such as diethyl ether, tetrahydrofuran and diphenyl ether, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, pentane and n-hexane And aliphatic hydrocarbons. These solvents may be used alone or as a mixture of two or more thereof.

  The reaction temperature can be set to any temperature from −60 ° C. to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually arbitrary in the range of 5 minutes to 100 hours. Can be set.

  Further, if necessary, a base such as hydrochloric acid, sulfuric acid, p-toluenesulfonic acid, etc., potassium carbonate, triethylamine, pyridine, 4- (dimethylamino) pyridine, sodium hydride, sodium hydroxide, potassium hydroxide, or Mitsunobu reaction using diethyl azodicarboxylate and triphenylphosphine or the like can be used.

  Moreover, the pyrazole derivative represented by General formula (22) and General formula (23) is made to react by reacting the compound represented by General formula (20), and the compound represented by well-known General formula (6). It can also be synthesized.

  In this reaction, the compound represented by the general formula (6) can be used in the range of 0.5 to 50 equivalents with respect to 1 equivalent of the compound represented by the general formula (20).

  If necessary, an acid such as hydrochloric acid, sulfuric acid or p-toluenesulfonic acid, or a base such as potassium carbonate, triethylamine, pyridine or 4- (dimethylamino) pyridine can be used.

  This reaction can be carried out without solvent, but a solvent may be used. For example, polar solvent such as N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolinone, water, methanol, ethanol, propanol, 2-propanol, ethylene glycol Alcohols such as diethyl ether, tetrahydrofuran and diphenyl ether, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, pentane and n-hexane And aliphatic hydrocarbons. These solvents may be used alone or as a mixture of two or more thereof.

  The reaction temperature can be set to any temperature from −60 ° C. to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually arbitrary in the range of 5 minutes to 100 hours. Can be set.

Further, by reacting the compound represented by the general formula (20) with the compound represented by the known general formula (7), the compound represented by the general formula (24) [wherein A ¹ , A ³ , R ² , R ⁴ , X ¹ , n and n1 have the same meaning as described above. ] Can be synthesized.

  In this reaction, the compound represented by the general formula (7) can be used in the range of 0.5 to 50 equivalents with respect to 1 equivalent of the compound represented by the general formula (20).

  If necessary, an acid such as hydrochloric acid, sulfuric acid or p-toluenesulfonic acid, or a base such as potassium carbonate, triethylamine, pyridine or 4- (dimethylamino) pyridine can be used.

  This reaction can be carried out without solvent, and a solvent may be used. For example, polar solvent such as N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolinone, water, methanol, ethanol, propanol, 2-propanol, ethylene glycol Alcohols such as diethyl ether, tetrahydrofuran and diphenyl ether, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, pentane and n-hexane And aliphatic hydrocarbons. These solvents may be used alone or in combination of two or more of them.

  The reaction temperature can be set to any temperature from −60 ° C. to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually arbitrary in the range of 5 minutes to 100 hours. Can be set.

  Manufacturing method E

Formula (30) [wherein R ³ , R ⁴ and X ¹ represent the same meaning as described above. The compound represented by the general formula (16) [wherein A ¹ , R ² and n1 represent the same meaning as described above, and L ₁ represents a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, —B (OH ) ₂ groups or —B (OR ⁵⁰ ) ₂ groups (wherein R ⁵⁰ represents C _{1 to} C ₆ alkyl which may be the same or different, or two G together represent —CH ₂ CH ₂ — or _{-C (CH 3) 2 C (} CH 3) 2 - represents a may be formed). And a compound represented by the general formula (31) [wherein A ¹ , R ² , R ³ , R ⁴ , X ¹ and n1 have the same meaning as described above]. Represent. ] Can be synthesized.

  The amount of the compound represented by the general formula (16) can be used in the range of 0.8 to 5 equivalents relative to 1 equivalent of the compound represented by the general formula (30).

  Some of the compounds represented by the general formula (16) used here are known compounds, and some of them are available as commercial products. Others can be easily synthesized according to the methods described in the literature.

  Examples of the catalyst that can be used in this reaction include palladium catalysts such as palladium-carbon, palladium chloride, palladium acetate, bis (triphenylphosphine) palladium dichloride, tetrakis (triphenylphosphine) palladium, copper metal, copper acetate (monovalent). ), Copper acetate (divalent), copper oxide (monovalent), copper oxide (divalent), copper iodide and the like. The catalyst is used in an amount of 0.001 to 1.0 equivalent, preferably 0.01 to 0.5 equivalent, more preferably 0.05 to 0, relative to 1 equivalent of the compound represented by the general formula (30). It can be used in the range of 2 equivalents.

  Examples of the base used include tertiary amine compounds such as pyridine, diisopropylethylamine, and triethylamine, and inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, and sodium bicarbonate. . The usage-amount of a base can be used in 0.1-10.0 equivalent with respect to 1 equivalent of compounds represented by General formula (30).

  This reaction can be carried out without a solvent, but a solvent may be used. For example, polar solvent such as N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolinone, water, methanol, ethanol, propanol, 2-propanol, ethylene glycol Alcohols such as diethyl ether, tetrahydrofuran and diphenyl ether, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, pentane and n-hexane And aliphatic hydrocarbons. These solvents may be used alone or as a mixture of two or more thereof.

  The reaction temperature can be set to any temperature from −60 ° C. to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually arbitrary in the range of 5 minutes to 100 hours. Can be set.

Next, by deprotecting the compound represented by the general formula (31) in concentrated hydrochloric acid, the general formula (32) [wherein A ¹ , R ² , R ³ , R ⁴ , X ¹ and n1 are the same as those described above] Means the same. ] Can be synthesized.

  This reaction can be carried out without a solvent, but a solvent may be used. For example, polar solvent such as N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolinone, water, methanol, ethanol, propanol, 2-propanol, ethylene glycol Alcohols such as diethyl ether, tetrahydrofuran and diphenyl ether, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, pentane and n-hexane And aliphatic hydrocarbons. These solvents may be used alone or as a mixture of two or more thereof.

  The reaction temperature can be set to any temperature from −60 ° C. to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually arbitrary in the range of 5 minutes to 100 hours. Can be set.

By reacting the compound represented by the general formula (32) thus obtained with the compound represented by the general formula (8), the compound represented by the general formula (33) [wherein A ¹ , R ² , R ³ , R ⁴ , X ¹ , X ^1a and n1 have the same meaning as described above. ] And general formula (34) [wherein A ¹ , R ² , R ³ , R ⁴ , X ¹ , X ^1a and n1 represent the same meaning as described above.] ] The pyrazole derivative represented by this can be obtained.

  This reaction can be carried out without solvent, but a solvent may be used. For example, polar solvent such as N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolinone, water, methanol, ethanol, propanol, 2-propanol, ethylene glycol Alcohols such as diethyl ether, tetrahydrofuran and diphenyl ether, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, pentane and n-hexane And aliphatic hydrocarbons. These solvents may be used alone or as a mixture of two or more thereof.

  The reaction temperature can be set to any temperature from −60 ° C. to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually arbitrary in the range of 5 minutes to 100 hours. Can be set.

  If necessary, bases such as hydrochloric acid, sulfuric acid, p-toluenesulfonic acid and the like, potassium carbonate, triethylamine, pyridine, 4- (dimethylamino) pyridine, sodium hydride, sodium hydroxide, potassium hydroxide, or Mitsunobu reaction using diethyl azodicarboxylate and triphenylphosphine or the like can be used.

  Manufacturing method F

Formula (39) [wherein ^{A 3,} R ^{4, X 1a} and n are as defined above. A pyrazole derivative represented by the general formula (22) can be synthesized by reacting the compound represented by the general formula (16) with the compound represented by the general formula (16) in the same manner as in the production method E.

  Manufacturing method G

General formula (41) [In formula, A < ³ >, R < ⁴ >, X < ¹ > and n represent the same meaning as the above. The pyrazole derivative represented by the general formula (24) can be synthesized by reacting the compound represented by the general formula (16) with the compound represented by the general formula (16) in the same manner as in the production method E. .

  The reaction of production method A to production method G may be carried out in an inert gas atmosphere such as nitrogen or argon if necessary.

  In the reaction of production method A to production method G, the reaction mixture after completion of the reaction is directly concentrated or dissolved in an organic solvent, concentrated after washing with water, or poured into ice water, and subjected to normal post-treatment such as concentration after extraction with organic solvent. The desired pyrazole derivative 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 General Formula (2-1) used in Production Method A can be synthesized, for example, as follows.

  Reaction formula 1

General formula (14) [wherein R ³ and R ⁴ represent the same meaning as described above. ] Can be synthesized by a known method such as Journal Heterocyclic Chemistry 1986, 23, 275.

That is, the compound represented by the general formula (14) is converted into a known formula according to a known method known from the literature, for example, the method described in Journal of Organic Chemistry 2004, 69, 5578. 16) and the compound represented by general formula (15) [wherein A ¹ , R ² , R ³ , R ⁴ and n1 are Represents the same meaning. ] Can be produced.

Furthermore, by reacting the compound represented by the general formula (15) with N, N′-dimethylformamide dimethyl acetal (DMFDMA) according to a known method known in the literature, the general formula (2-1) [wherein A ¹ , R ² , R ³ , R ⁴ and n1 have the same meaning as described above. The compound represented by this can be manufactured.

  The compound represented by the general formula (12) used in the production method C can be synthesized, for example, as follows.

  Reaction formula 2

The general formula (17) [wherein ^{A 1, R 2, R 3} , R 4, J b and n1 represent the same meanings as described above. ] Can be synthesized by a known method such as Journal Heterocyclic Chemistry 1981, Vol. 18, p.

That is, the compound represented by the general formula (17) is converted into B (OR ⁵⁰ ) according to a known method known in the literature, for example, the method described in Journal of Heterocyclic Chemistry 2004, 41, 931. ₃ [wherein R ⁵⁰ may be the same or different and represents a C _{1 to} C ₆ alkyl, or two R ⁵⁰ together represent —CH ₂ CH ₂ — or —C (CH ₃ ) ₂ C (CH ₃ ) ₂ — may be formed. ] Or-[B (OR ⁵⁰ ) ₂ ] ₂ [wherein R ⁵⁰ represents the same meaning as described above.] ] Is reacted in the presence of a transition metal catalyst catalyst such as palladium and a base, to obtain a compound represented by the general formula (12) [wherein A ¹ , R ² , R ³ , R ⁴ and n1 are as defined above. R ⁵⁰ represents the same meaning and R ⁵⁰ represents a hydrogen atom or C _{1 to} C ₆ alkyl which may be the same or different, or two R ⁵⁰ together represent —CH ₂ CH ₂ — or —C (CH ₃ ). ₂ C (CH ₃ ) ₂ — may be formed. The compound represented by this can be manufactured.

Some of the compounds represented by B (OR ⁵⁰ ) ₃ or-[B (OR ⁵⁰ ) ₂ ] ₂ used here are known compounds, and some of them are commercially available. Others can be easily synthesized according to known methods described in the literature.

  The compound represented by General Formula (20) used in Production Method D can be synthesized, for example, as follows.

  Reaction formula 3

Formula (18) [wherein ^{A 3} and ^{R 4} are as defined above, n represents an integer of 0 to 3. ] Can be synthesized by known methods such as tetrahedron 2006, 62, 11704.

That is, the compound represented by the general formula (18) is reacted with the compound represented by the known general formula (16) similarly to the above reaction formula 1 in the presence of a transition metal catalyst such as palladium and a base. In general formula (19) [wherein A ¹ , A ³ , R ² , R ⁴ , n and n1 represent the same meaning as described above. ] Can be easily produced.

Further, by reacting the compound represented by the general formula (19) with N, N′-dimethylformamide dimethyl acetal (DMFDMA) according to a known method known in the literature, the compound represented by the general formula (20) [wherein A ¹ , A ³ , R ² , R ⁴ , n and n1 represent the same meaning as described above. ] Can be easily produced.

  The compound represented by the general formula (30) used in the production method E can be synthesized, for example, as follows.

  Reaction formula 4

That is, the general formula (25) [wherein R ³ , R ⁴ and R ⁵⁰ represent the same meaning as described above. The compound represented by general formula (26) according to a known method known in the literature, for example, the method described in Heterocycles 1988, 27, 2443, etc. [formula medium J ^b are as defined above. ] In general formula (27) [wherein R ³ , R ⁴ and R ⁵⁰ represent the same meaning as described above. The compound represented by this can be manufactured. Some of the compounds represented by the general formula (25) are known compounds, and some of them are commercially available. Others can be synthesized according to known methods described in the literature.

Next, the compound represented by the general formula (27) and the general formula (28) [wherein X ¹ and J ^b represent the same meaning as described above. The compound represented by the general formula (29) [wherein R ³ , R ⁴ and X ¹ represent the same meaning as described above]. ] Can be synthesized.

Subsequently, the compound represented by the general formula (29) is converted into a compound represented by the general formula (30) [wherein R ³ in the formula, by a known method known in the literature, for example, the method described in Tetrahedron 2008, 64, 7745, etc. R ⁴ and X ¹ represent the same meaning as described above. ] Can be synthesized.

  Some of the compounds represented by the general formulas (25) and (28) used in Reaction Scheme 4 are known compounds, and some of them are available as commercial products. Others can be easily synthesized according to known methods described in the literature.

  The compound represented by General Formula (39) used in Production Method F can be synthesized, for example, as follows.

  Reaction formula 5

That is, by reacting general formula (18) with ethyl vinyl ether according to a known method known in the literature, for example, the method described in Heterocycles 2003, 60, 879, etc., general formula (35) [formula In the middle, A ³ , R ⁴ and n represent the same meaning as described above, and EE represents —CH (CH ₃ ) OCH ₂ CH ₃ . ] Can be synthesized.

Next, the compound represented by the general formula (35) is reacted with N, N′-dimethylformamide dimethyl acetal (DMFDMA) according to a known method known in the literature, thereby obtaining the general formula (36) [in the formula A ³ , R ⁴ , n and EE represent the same meaning as described above. ] Can be easily produced.

Subsequently, from the compound represented by the general formula (36), using the same method as the production method A, the general formula (37) [wherein A ³ , R ⁴ , n and EE represent the same meaning as described above. ] And the general formula (38) [wherein A ³ , R ⁴ , X ^1a , n and EE represent the same meaning as described above. ] Can be synthesized.

Furthermore, by reacting with an acid according to a known method known from the literature from the compound represented by the general formula (38), for example, the method described in Bioorganic and Medicinal Chemistry Letter 2009, Vol. 19, p. formula (39) [wherein ^{a 3,} R ^{4, X 1a} and n are as defined above. ] Can be synthesized.

  The compound represented by the general formula (41) used in the production method G can be synthesized, for example, as follows.

  Reaction formula 6

That is, by reacting the compound represented by the general formula (36) and the general formula (7) using the same method as the production method A, the compound represented by the general formula (40) [wherein A ³ , R ⁴ , X ¹ , n and EE represent the same meaning as described above. ] Can be synthesized.

Next, by reacting the compound represented by the general formula (40) using the same method as the above reaction formula 5, the general formula (41) [wherein A ³ , R ⁴ , X ¹ and n are the above-mentioned Means the same. ] Can be synthesized.

Specific examples of the compound included in the present invention include compounds shown in Tables 3 to 10. However, the compounds in Tables 3 to 10 are for illustrative purposes, and the present invention is not limited thereto. In the table, the substituent described as Me represents a methyl group, hereinafter, Et represents an ethyl group, n-Pr and Pr-n represent normal propyl groups, i-Pr and Pr-i. Is an isopropyl group, c-Pr and Pr-c are cyclopropyl groups, n-Bu and Bu-n normal butyl groups, s-Bu and Bu-s are secondary butyl groups, i-Bu and Bu-i. Is an isobutyl group, t-Bu and Bu-t are tertiary butyl groups, c-Bu and Bu-c are cyclobutyl groups, n-Pen and Pen-n are normal pentyl groups, c-Pen and Pen- c is a cyclopentyl group, n-Hex and Hex-n are normal hexyl groups, c-Hex and Hex-c are cyclohexyl groups, Hept is a heptyl group, Oct is an octyl group, and Ph is a fethyl group. It represents Le group, respectively. In the table, D2-7a, D2-32a, D2-32b, D2-33a, D2-34a, D2-34b, D2-37a, D2-37b, D2-81a, D2-82a, D2-108a and D2 -108b represents the following structural formulas, D2-32b and numbers written in each structural formula D2-37b represents the substitution position of ^{X 2,} numbers written in the structural formula of D2-108b is Z ² is represented.

  Table 3

[Table 3]
――――――――――――――――――――――
X ¹ X ^1a
――――――――――――――――――――――
HH
SMe H
H Me
H Et
H n-Pr
H i-Pr
H t-Bu
H CH ₂ C≡CH
H CH ₂ CHF ₂
H CH ₂ CH (OEt) ₂
H CH ₂ C (Me) = NOMe
H CH ₂ CN
H CH ₂ C (O) OMe
H CH ₂ C (O) NHMe
H CH ₂ OMe
H CH ₂ OCH ₂ CF ₃
H CH ₂ SMe
H CH ₂ S (O) Me
H CH ₂ S (O) ₂ Me
H CH ₂ SEt
H CH ₂ S (O) Et
H CH ₂ S (O) ₂ Et
H CH ₂ SPr-i
H CH ₂ S (O) Pr-i
H CH ₂ S (O) ₂ Pr-i
H CH ₂ SCH ₂ CF ₃
H CH ₂ S (O) CH ₂ CF ₃
H CH ₂ S (O) ₂ CH ₂ CF ₃
H CH ₂ S (= NCN) Me
H CH ₂ S (O) (= NCN) Me
――――――――――――――――――――――
[Table 3] (continued)
――――――――――――――――――――――
X ¹ X ^1a
――――――――――――――――――――――
H CH ₂ S (= NNO ₂ ) Me
H CH ₂ S (O) (= NNO ₂ ) Me
H CH ₂ CH ₂ SMe
H CH ₂ CH ₂ S (O) Me
H CH ₂ CH ₂ S (O) ₂ Me
H CH ₂ SC (O) Me
H CH ₂ SCN
HC (O) NHEt
HC (O) NHCH ₂ CF ₃
HC (O) N (Me) Et
HC (S) NHEt
HC (O) Me
HC (O) OEt
HC (O) SMe
HC (O) CH ₂ SMe
HC (O) CH ₂ CH ₂ SMe
HS (O) ₂ Me
HS (O) ₂ {D2-108b (4-Me)}
HS (O) ₂ NMe ₂
H D2-32a
H D2-33a
H D2-34a
H D2-37a
H D2-81a
H D2-82a
H D2-108b (2-CF ₃ )
H D2-32b (3-Cl)
H D2-32b (5-Cl)
H CH ₂ CH ₂ CH (Me) S (O) ₂ Me
H CH ₂ CH ₂ CH ₂ CH ₂ SMe
H CH ₂ CH ₂ CH ₂ CH ₂ S (O) Me
H CH ₂ CH ₂ CH ₂ CH ₂ S (O) ₂ Me
H CH ₂ CH ₂ CH ₂ CH ₂ SEt
――――――――――――――――――――――
[Table 3] (continued)
――――――――――――――――――――――
X ¹ X ^1a
――――――――――――――――――――――
H CH ₂ CH ₂ CF ₃
H CH ₂ CF ₃
Me CH ₂ CF ₃
OH CH ₂ CF ₃
OMe CH ₂ CF ₃
SMe CH ₂ CF ₃
NH ₂ CH ₂ CF ₃
NHC (O) CH ₃ CH ₂ CF ₃
NHC (O) CF ₃ CH ₂ CF ₃
H D2-32b (6-Cl)
H D2-34b (2-Cl)
H D2-37b (4,6-bisCF ₃ )
H CH ₂ (D2-7a)
H CH ₂ (D2-32a)
H CH ₂ (D2-108a)
OH H
OCH ₂ CF ₃ H
OCH ₂ CF ₃ Me
NHC (O) Me CH ₂ CF ₃
CH ₂ SMe H
CH ₂ S (O) Me H
CH ₂ S (O) ₂ Me H
-OCH ₂ CH _2-
H CH ₂ CH ₂ CH ₂ SMe
H CH ₂ CH ₂ CH ₂ S (O) Me
H CH ₂ CH ₂ CH ₂ S (O) ₂ Me
H CH (Me) CH ₂ CH ₂ SMe
H CH (Me) CH ₂ CH ₂ S (O) Me
H CH (Me) CH ₂ CH ₂ S (O) ₂ Me
H CH ₂ CH (Me) CH ₂ SMe
――――――――――――――――――――――
[Table 3] (continued)
――――――――――――――――――――――
X ¹ X ^1a
――――――――――――――――――――――
H CH ₂ CH (Me) CH ₂ S (O) Me
H CH ₂ CH (Me) CH ₂ S (O) ₂ Me
H CH ₂ CH ₂ CH (Me) SMe
H CH ₂ CH ₂ CH (Me) S (O) Me
H CH ₂ CH ₂ CH (Me) S (O) ₂ Me
H CH ₂ CH ₂ CH ₂ SEt
H CH ₂ CH ₂ CH ₂ S (O) Et
H CH ₂ CH ₂ CH ₂ S (O) ₂ Et
H CH (Me) CH ₂ CH ₂ SEt
H CH (Me) CH ₂ CH ₂ S (O) Et
H CH (Me) CH ₂ CH ₂ S (O) ₂ Et
H CH ₂ CH (Me) CH ₂ SEt
H CH ₂ CH (Me) CH ₂ S (O) Et
H CH ₂ CH (Me) CH ₂ S (O) ₂ Et
H CH ₂ CH ₂ CH (Me) SEt
H CH ₂ CH ₂ CH (Me) S (O) Et
H CH ₂ CH ₂ CH (Me) S (O) ₂ Et
H CH ₂ CH ₂ CH ₂ SPr-n
H CH ₂ CH ₂ CH ₂ S (O) Pr-n
H CH ₂ CH ₂ CH ₂ S (O) ₂ Pr-n
H CH (Me) CH ₂ CH ₂ SPr-n
H CH (Me) CH ₂ CH ₂ S (O) Pr-n
H CH (Me) CH ₂ CH ₂ S (O) ₂ Pr-n
H CH ₂ CH (Me) CH ₂ SPr-n
H CH ₂ CH (Me) CH ₂ S (O) Pr-n
H CH ₂ CH (Me) CH ₂ S (O) ₂ Pr-n
H CH ₂ CH ₂ CH (Me) SMe
H CH ₂ CH ₂ CH (Me) S (O) Me
H CH ₂ CH ₂ CH ₂ CH ₂ S (O) Et
H CH ₂ CH ₂ CH ₂ CH ₂ S (O) ₂ Et
H CH ₂ CH ₂ CH ₂ CH ₂ SPr-n
H CH ₂ CH ₂ CH ₂ CH ₂ S (O) Pr-n
H CH ₂ CH ₂ CH ₂ CH ₂ S (O) ₂ Pr-n
―――――――――――――――――――
Table 4

[Table 4]
―――――――――――――――――――――――――
X ^1-1 X ^1-2
―――――――――――――――――――――――――
HH
Me H
CH ₂ OH H
CH ₂ Cl H
CF ₂ CF ₃ H
SMe H
S (O) Me H
S (O) ₂ Me H
SEt H
S (O) Et H
S (O) ₂ Et H
CH ₂ SMe H
CH ₂ S (O) Me H
CH ₂ S (O) ₂ Me H
C (O) NHEt H
C (O) NHCH ₂ CF ₃ H
C (O) OEt H
D2-32a H
H Me
H CH ₂ OH
H CH ₂ Cl
H CF ₂ CF ₃
H SMe
HS (O) Me
HS (O) ₂ Me
H SEt
HS (O) Et
HS (O) ₂ Et
H CH ₂ SMe
H CH ₂ S (O) Me
―――――――――――――――――――――――――
[Table 4] (continued)
―――――――――――――――――――――――――
X ^1-1 X ^1-2
―――――――――――――――――――――――――
H CH ₂ S (O) ₂ Me
HC (O) NHEt
HC (O) NHCH ₂ CF ₃
HC (O) OEt
H D2-32a
Me Me
CH ₂ CH ₂ CH ₂ SMe H
CH ₂ CH ₂ CH ₂ S (O) Me H
CH ₂ CH ₂ CH ₂ S (O) ₂ Me H
CH (Me) CH ₂ CH ₂ SMe H
CH (Me) CH ₂ CH ₂ S (O) Me H
CH (Me) CH ₂ CH ₂ S (O) ₂ Me H
CH ₂ CH (Me) CH ₂ SMe H
CH ₂ CH (Me) CH ₂ S (O) Me H
CH ₂ CH (Me) CH ₂ S (O) ₂ Me H
H CH ₂ CH ₂ CH (Me) SMe
H CH ₂ CH ₂ CH (Me) S (O) Me
H CH ₂ CH ₂ CH (Me) S (O) ₂ Me
H CH ₂ CH ₂ CH ₂ SEt
H CH ₂ CH ₂ CH ₂ S (O) Et
H CH ₂ CH ₂ CH ₂ S (O) ₂ Et
H CH (Me) CH ₂ CH ₂ SEt
H CH (Me) CH ₂ CH ₂ S (O) Et
H CH (Me) CH ₂ CH ₂ S (O) ₂ Et
H CH ₂ CH (Me) CH ₂ SEt
H CH ₂ CH (Me) CH ₂ S (O) Et
H CH ₂ CH (Me) CH ₂ S (O) ₂ Et
H CH ₂ CH ₂ CH (Me) SEt
H CH ₂ CH ₂ CH (Me) S (O) Et
H CH ₂ CH ₂ CH (Me) S (O) ₂ Et
H CH ₂ CH ₂ CH ₂ SPr-n
H CH ₂ CH ₂ CH ₂ S (O) Pr-n
H CH ₂ CH ₂ CH ₂ S (O) ₂ Pr-n
H CH (Me) CH ₂ CH ₂ SPr-n
―――――――――――――――――――――――――
[Table 4] (continued)
―――――――――――――――――――――――――
X ^1-1 X ^1-2
―――――――――――――――――――――――――
CH ₂ CH ₂ CH (Me) SMe H
CH ₂ CH ₂ CH (Me) S (O) Me H
CH ₂ CH ₂ CH (Me) S (O) ₂ Me H
CH ₂ CH ₂ CH ₂ SEt H
CH ₂ CH ₂ CH ₂ S (O) Et H
CH ₂ CH ₂ CH ₂ S (O) ₂ Et H
CH (Me) CH ₂ CH ₂ SEt H
CH (Me) CH ₂ CH ₂ S (O) Et H
CH (Me) CH ₂ CH ₂ S (O) ₂ Et H
CH ₂ CH (Me) CH ₂ SEt H
CH ₂ CH (Me) CH ₂ S (O) Et H
CH ₂ CH (Me) CH ₂ S (O) ₂ Et H
CH ₂ CH ₂ CH (Me) SEt H
CH ₂ CH ₂ CH (Me) S (O) Et H
CH ₂ CH ₂ CH (Me) S (O) ₂ Et H
CH ₂ CH ₂ CH ₂ SPr-n H
CH ₂ CH ₂ CH ₂ S (O) Pr-n H
CH ₂ CH ₂ CH ₂ S (O) ₂ Pr-n H
CH (Me) CH ₂ CH ₂ SPr-n H
CH (Me) CH ₂ CH ₂ S (O) Pr-n H
CH (Me) CH ₂ CH ₂ S (O) ₂ Pr-n H
CH ₂ CH (Me) CH ₂ SPr-n H
CH ₂ CH (Me) CH ₂ S (O) Pr-n H
CH ₂ CH (Me) CH ₂ S (O) ₂ Pr-n H
CH ₂ CH ₂ CH (Me) SMe H
CH ₂ CH ₂ CH (Me) S (O) Me H
CH ₂ CH ₂ CH (Me) S (O) ₂ Me H
CH ₂ CH ₂ CH ₂ CH ₂ SMe H
CH ₂ CH ₂ CH ₂ CH ₂ S (O) Me H
CH ₂ CH ₂ CH ₂ CH ₂ S (O) ₂ Me H
CH ₂ CH ₂ CH ₂ CH ₂ SEt H
[Table 4] (continued)
―――――――――――――――――――――――――
X ^1-1 X ^1-2
―――――――――――――――――――――――――
CH ₂ CH ₂ CH ₂ CH ₂ S (O) Et H
CH ₂ CH ₂ CH ₂ CH ₂ S (O) ₂ Et H
CH ₂ CH ₂ CH ₂ CH ₂ SPr-n H
CH ₂ CH ₂ CH ₂ CH ₂ S (O) Pr-n H
CH ₂ CH ₂ CH ₂ CH ₂ S (O) ₂ Pr-n H
H CH ₂ CH ₂ CH ₂ SMe
H CH ₂ CH ₂ CH ₂ S (O) Me
H CH ₂ CH ₂ CH ₂ S (O) ₂ Me
H CH (Me) CH ₂ CH ₂ SMe
H CH (Me) CH ₂ CH ₂ S (O) Me
H CH (Me) CH ₂ CH ₂ S (O) ₂ Me
H CH ₂ CH (Me) CH ₂ SMe
H CH ₂ CH (Me) CH ₂ S (O) Me
H CH ₂ CH (Me) CH ₂ S (O) ₂ Me
H CH (Me) CH ₂ CH ₂ S (O) Pr-n
H CH (Me) CH ₂ CH ₂ S (O) ₂ Pr-n
H CH ₂ CH (Me) CH ₂ SPr-n
H CH ₂ CH (Me) CH ₂ S (O) Pr-n
H CH ₂ CH (Me) CH ₂ S (O) ₂ Pr-n
H CH ₂ CH ₂ CH (Me) SMe
H CH ₂ CH ₂ CH (Me) S (O) Me
H CH ₂ CH ₂ CH (Me) S (O) ₂ Me
H CH ₂ CH ₂ CH ₂ CH ₂ SMe
H CH ₂ CH ₂ CH ₂ CH ₂ S (O) Me
H CH ₂ CH ₂ CH ₂ CH ₂ S (O) ₂ Me
H CH ₂ CH ₂ CH ₂ CH ₂ SEt
H CH ₂ CH ₂ CH ₂ CH ₂ S (O) Et
H CH ₂ CH ₂ CH ₂ CH ₂ S (O) ₂ Et
H CH ₂ CH ₂ CH ₂ CH ₂ SPr-n
H CH ₂ CH ₂ CH ₂ CH ₂ S (O) Pr-n
H CH ₂ CH ₂ CH ₂ CH ₂ S (O) ₂ Pr-n
―――――――――――――――――――――――――
Table 5

[Table 5]
――――――――――――――――――――――――――――――――
X ^1-1 X ^1-2 X ^1-3
――――――――――――――――――――――――――――――――
Cl HH
NO ₂ HH
Me HH
Et HH
CF ₃ HH
CH = NOMe HH
SMe HH
S (O) Me HH
S (O) ₂ Me HH
SCF ₃ HH
S (O) CF ₃ HH
S (O) ₂ CF ₃ HH
CH ₂ SMe HH
CH ₂ S (O) Me HH
CH ₂ S (O) ₂ Me HH
OMe HH
OCF ₃ HH
C (O) NHMe HH
C (O) NHCH ₂ CF ₃ HH
C (O) Me HH
NHC (O) Me HH
H Cl H
H NO ₂ H
H Me H
H Et H
H CF ₃ H
H CH = NOMe H
H SMe H
HS (O) Me H
HS (O) ₂ Me H
H SCF ₃ H
HS (O) CF ₃ H
HS (O) ₂ CF ₃ H
H CH ₂ SMe H
H CH ₂ S (O) Me H
H CH ₂ S (O) ₂ Me H
――――――――――――――――――――――――――――――――
[Table 5] (continued)
――――――――――――――――――――――――――――――――
X ^1-1 X ^1-2 X ^1-3
――――――――――――――――――――――――――――――――
H OMe H
H OCF ₃ H
HC (O) NHMe H
HC (O) NHCH ₂ CF ₃ H
HC (O) Me H
H NHC (O) Me H
HH Cl
HH NO ₂
HH Me
HH Et
HH CF ₃
HH CH = NOMe
HH SMe
HHS (O) Me
HHS (O) ₂ Me
HH SCF ₃
HHS (O) CF ₃
HHS (O) ₂ CF ₃
HH CH ₂ SMe
HH CH ₂ S (O) Me
HH CH ₂ S (O) ₂ Me
HH OMe
HH OCF ₃
HHC (O) NHMe
HHC (O) NHCH ₂ CF ₃
HHC (O) Me
HH NHC (O) Me
――――――――――――――――――――――――――――――――
Table 6

[Table 6]
――――――――――――――――――
A ³ X ^1a
――――――――――――――――――
CH ₂ H
CH ₂ Me
CH ₂ Et
CH ₂ CH ₂ CN
CH ₂ CH ₂ CF ₃
CH ₂ CH ₂ OCH ₃
CH ₂ CH ₂ SCH ₃
CH ₂ CH ₂ S (O) CH ₃
CH ₂ CH ₂ S (O) ₂ CH ₃
CH ₂ D2-37a
CHMe CH ₂ CF ₃
CHMe H
CHMe Me
CHMe Et
CHMe CH ₂ CN
CHMe CH ₂ OCH ₃
CHMe CH ₂ SCH ₃
CHMe CH ₂ S (O) CH ₃
CHMe CH ₂ S (O) ₂ CH ₃
CHMe D2-37a
C (Me) ₂ H
C (Me) ₂ Me
C (Me) ₂ Et
C (Me) ₂ CH ₂ CN
C (Me) ₂ CH ₂ CF ₃
―――――――――――――――――――
[Table 6] (continued)
――――――――――――――――――
A ³ X ^1a
――――――――――――――――――
C (Me) ₂ CH ₂ OCH ₃
C (Me) ₂ CH ₂ SCH ₃
C (Me) ₂ CH ₂ S (O) CH ₃
C (Me) ₂ CH ₂ S (O) ₂ CH ₃
C (Me) ₂ D2-37a
OH
O Me
O Et
O CH ₂ CN
O CH ₂ CF ₃
O CH ₂ OCH ₃
O CH ₂ SCH ₃
O CH ₂ S (O) CH ₃
O CH ₂ S (O) ₂ CH ₃
O D2-37a
SH
S Me
S Et
S CH ₂ CN
S CH ₂ CF ₃
S CH ₂ OCH ₃
S CH ₂ SCH ₃
S CH ₂ S (O) CH ₃
S CH ₂ S (O) ₂ CH ₃
S D2-37a
――――――――――――――――――
Table 7

[Table 7]
――――――――――――――――――
A ³ X ¹
――――――――――――――――――
CH ₂ H
CH ₂ Me
CH ₂ Et
CH ₂ CH ₂ CN
CH ₂ CH ₂ CF ₃
CH ₂ CH ₂ OCH ₃
CH ₂ CH ₂ SCH ₃
CH ₂ CH ₂ S (O) CH ₃
CH ₂ CH ₂ S (O) ₂ CH ₃
CH ₂ D2-37a
CHMe CH ₂ CF ₃
CHMe H
CHMe Me
CHMe Et
CHMe CH ₂ CN
CHMe CH ₂ OCH ₃
CHMe CH ₂ SCH ₃
CHMe CH ₂ S (O) CH ₃
CHMe CH ₂ S (O) ₂ CH ₃
CHMe D2-37a
C (Me) ₂ H
C (Me) ₂ Me
C (Me) ₂ Et
C (Me) ₂ CH ₂ CN
C (Me) ₂ CH ₂ CF ₃
C (Me) ₂ CH ₂ OCH ₃
――――――――――――――――――
[Table 7] (continued)
――――――――――――――――――
A ³ X ¹
――――――――――――――――――
C (Me) ₂ CH ₂ SCH ₃
C (Me) ₂ CH ₂ S (O) CH ₃
C (Me) ₂ CH ₂ S (O) ₂ CH ₃
C (Me) ₂ D2-37a
OH
O Me
O Et
O CH ₂ CN
O CH ₂ CF ₃
O CH ₂ OCH ₃
O CH ₂ SCH ₃
O CH ₂ S (O) CH ₃
O CH ₂ S (O) ₂ CH ₃
O D2-37a
SH
S Me
S Et
S CH ₂ CN
S CH ₂ CF ₃
S CH ₂ OCH ₃
S CH ₂ SCH ₃
S CH ₂ S (O) CH ₃
S CH ₂ S (O) ₂ CH ₃
S D2-37a
――――――――――――――――――
Table 8

[Table 8]
――――――――――――――――――――――――――――――
A ³ X ^1a
――――――――――――――――――――――――――――――
CH ₂ H
CH ₂ Me
CH ₂ Et
CH ₂ CH ₂ CN
CH ₂ CH ₂ CF ₃
CH ₂ CH ₂ OCH ₃
CH ₂ CH ₂ SCH ₃
CH ₂ CH ₂ S (O) CH ₃
CH ₂ CH ₂ S (O) ₂ CH ₃
CH ₂ D2-37a
――――――――――――――――――――――――――――――
Table 9

[Table 9]
――――――――――――――――――――――――――――――
A ³ X ^1a
――――――――――――――――――――――――――――――
CH ₂ H
CH ₂ Me
CH ₂ Et
CH ₂ CH ₂ CN
CH ₂ CH ₂ CF ₃
CH ₂ CH ₂ OCH ₃
CH ₂ CH ₂ SCH ₃
CH ₂ CH ₂ S (O) CH ₃
CH ₂ CH ₂ S (O) ₂ CH ₃
CH ₂ D2-37a
――――――――――――――――――――――――――――――
Table 10

[Table 10]
――――――――――――――
X ^1-1
――――――――――――――
CH ₂ CF ₃
CH ₂ SCH ₃
CH ₂ S (O) CH ₃
CH ₂ S (O) ₂ CH ₃
CH ₂ CH ₂ CH ₂ SMe
CH ₂ CH ₂ CH ₂ S (O) Me
CH ₂ CH ₂ CH ₂ S (O) ₂ Me
CH (Me) CH ₂ CH ₂ SMe
CH (Me) CH ₂ CH ₂ S (O) Me
CH (Me) CH ₂ CH ₂ S (O) ₂ Me
CH ₂ CH (Me) CH ₂ SMe
CH ₂ CH (Me) CH ₂ S (O) Me
CH ₂ CH (Me) CH ₂ S (O) ₂ Me
CH ₂ CH ₂ CH (Me) SMe
CH ₂ CH ₂ CH (Me) S (O) Me
CH ₂ CH ₂ CH (Me) S (O) ₂ Me
CH ₂ CH ₂ CH ₂ SEt
CH ₂ CH ₂ CH ₂ S (O) Et
CH ₂ CH ₂ CH ₂ S (O) ₂ Et
CH (Me) CH ₂ CH ₂ SEt
CH (Me) CH ₂ CH ₂ S (O) Et
CH (Me) CH ₂ CH ₂ S (O) ₂ Et
CH ₂ CH (Me) CH ₂ SEt
CH ₂ CH (Me) CH ₂ S (O) Et
CH ₂ CH (Me) CH ₂ S (O) ₂ Et
CH ₂ CH ₂ CH (Me) SEt
――――――――――――――
[Table 10] (continued)
――――――――――――――
X ^1-1
――――――――――――――
CH ₂ CH ₂ CH (Me) S (O) Et
CH ₂ CH ₂ CH (Me) S (O) ₂ Et
CH ₂ CH ₂ CH ₂ SPr-n
CH ₂ CH ₂ CH ₂ S (O) Pr-n
CH ₂ CH ₂ CH ₂ S (O) ₂ Pr-n
CH (Me) CH ₂ CH ₂ SPr-n
CH (Me) CH ₂ CH ₂ S (O) Pr-n
CH (Me) CH ₂ CH ₂ S (O) ₂ Pr-n
CH ₂ CH (Me) CH ₂ SPr-n
CH ₂ CH (Me) CH ₂ S (O) Pr-n
CH ₂ CH (Me) CH ₂ S (O) ₂ Pr-n
CH ₂ CH ₂ CH (Me) SMe
CH ₂ CH ₂ CH (Me) S (O) Me
CH ₂ CH ₂ CH (Me) S (O) ₂ Me
CH ₂ CH ₂ CH ₂ CH ₂ SMe
CH ₂ CH ₂ CH ₂ CH ₂ S (O) Me
CH ₂ CH ₂ CH ₂ CH ₂ S (O) ₂ Me
CH ₂ CH ₂ CH ₂ CH ₂ SEt
CH ₂ CH ₂ CH ₂ CH ₂ S (O) Et
CH ₂ CH ₂ CH ₂ CH ₂ S (O) ₂ Et
CH ₂ CH ₂ CH ₂ CH ₂ SPr-n
CH ₂ CH ₂ CH ₂ CH ₂ S (O) Pr-n
CH ₂ CH ₂ CH ₂ CH ₂ S (O) ₂ Pr-n
――――――――――――――
The parasite control agent containing the pyrazole derivative represented by the general formula (1) or a salt thereof as an active ingredient is an arthropod as an external or internal parasite that parasitizes companion animals, pet animals, livestock, and poultry. Parasitic invertebrates such as animals, nematodes, bald worms, tapeworms, flukes, spores, ciliates and flagellates can be effectively controlled.

Specific examples of animals that can be used for the control of the parasitic parasitic invertebrates of the present invention include the capuchin monkeys Tufted capuchin (Cebus apella) and other cynomolgus monkeys (Cebidae), cynomolgus Crab- Eating macaque (Macaca fascicularis), rhesus monkey Rhesus macaque (Macaca mulatta), etc. Rabidae (Leporidae), Chinchilla Long-tailed chinchilla (Chinchilla lanigera) Djungarian hamster (Phodopus sungorus), Mongolian gerbil Chinese hamster (Cri cetulus griseus) and other species (Cricetidae); Squiridae (Sciuridae), Dromedary (Camelus dromedarius), Bactrian camel (Camelus bactrianus), Alpaca (Vicugna pacos), Lamela Llama (Lama glama), etc. (Camelidae), pig Pig (Sus), etc. Wild Boar (Suidae), Reindeer Reindeer (Rangifer tarandus), Red Deer (Cervus elaphus), Deer Family (Cervidae), Yak Yak (Bos grunniens), Cattle Cattle (Bos taurus), Asian Buffalo (Bubalus arnee) ), Goat (Capra hircus), Sheep (Ovis aries), etc. Bovidae, Domestic cat Cat (Felis silvestris catus) Felidae, Dogs (Canis lupus familiaris), Red fox (Vulpes vulpes) and other canines (Canidae), European mink European mink (Mustela lutreola), American mink American mink (Mustela vison), Ferret Ferret (Mustela putorius furo) and other weasels (Mustelidae), donkeys (Equus asinus), horses (Equiuse) such as Horse (Equus caballus), red kangaroos (Macropus rufus) and other kangaroos (Macropodidae) Mammals belonging to,
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. Terrestrial canes (Sturnidae), red avadavat (Amandava amandava), zebra finch (Taeniopygia guttata), red pine Bengalese finch (Lonchura striata var. Domestica), etc. (Estrildidae) , Birds (Aves) belonging to the family Atri (Fringillidae) such as 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) reptiles (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. ) And other cichlids (Cichlidae), bluefin tuna Pacific bluefin tuna (Thunnus orientalis) and other mackereles (Scombridae), trough puffer Japanese pufferfish (Takifugu rubripes) and other pelagic fishes (Actinopterygii) Of these, among others, camelid, wild boar, bovine, feline, The parasite control agent of the present invention exerts an excellent effect in controlling parasites parasitizing mammals belonging to the family and equine family, and is particularly effective in controlling ectoparasites of feline and canine mammals. However, the target animals that can be used to control parasitic invertebrates using the parasite control agent of the present invention are not limited to these.

Specific examples of harmful parasitic invertebrates and sanitary pests that can be controlled using the present parasite and sanitary pest control agents include the Argentine ant Argentine ant (Linepithema humile) and the Guntai ant Army ant (Eciton burchelli, E schmitti), Japanese carpenter ant (Camponotus japonicus), Japanese black ant Pharaoh ant (Monomorium pharaonis), Bulldog ant Bulldog ant (Myrmecia spp.), Fire ant Fire ant (Solenopsis spp.), Asian giant hornet ), Hymenoptera insects such as Japanese yellow hornet (Vespa simillima)
The tsetse fly (Glossina morsitans, G. palpalis), the white fly, Forest fly (Hippobosca equina), the sheep fly, Sheep ked (Melophagus ovinus), the fly fly Lesser house fly (Fannia canicularis), the sheep head fly (Hydrot weir) fly (Morellia simplex), Face fly (Musca autumnalis), Housefly (Musca domestica), Australian bush fly (Musca vetustissima), Horn flies Horn fly (Haematobia irritans), Fly flies Stable fly (Stomoxys calcitrans) (Calliphora lata), Bottle fly (Calliphora vicina), Old World screw-worm fly (Chrysomya bezziana), Blow fly (Chrysomya chloropyga), Okikin fly Oriental latrine fly (Chrysomya megacephala), New Zealand ld screw-worm fly (Cochliomyia hominivorax), black blow fly (Phormia regina), northern fly fly (Protophormia terraenovae), sheep fly Australian sheep blowfly (Lucilia cuprina), green bottle fly (Lucilia illustris), common green fly Bottle fly (Lucilia sericata), Bot flies (Cuterebra spp.), Human fly botfly (Dermatobia hominis), Horse flounder Horse nose bot fly (Gasterophilus haemorrhoidalis), Horse fly bot fly (Gasterophilus intestinalis) nasalis), Bullflies Warble fly (Hypoderma bovis), Common cattle grub (Hypoderma lineatum), Sheep nasal bot fly (Oestrus ovis), Fresh fly Flesh fly (Sarcophaga carnaria), Frensh fly (Sarcophaga) Deer Fly Splayed deerfly (Chrysops caecutiens), Mekurabu Deer fly (Chrysops suavis), Common Horse Fly (Haematopota pluvialis), Green Head Horse Fly (Tabanus nigrovittatus), Cow Abuse Horse fly (Tabanus trigonus), Chicken Nukaca Biting midge (Culicoides arakawae), Black gnat (Leptoconops nipponensis), Kashio Ayuyu (Prosimulium yezoensis), Black fly (Simulium ochraceum), Gambier squirrel (Anopheles geleae), Sina Anopheles lesteri, Yellow fever mosquito (Aedes aegypti), Asian tiger mosquito (Aedes albopictus), Chikaeka House mosquito (Culex pipiens molestus), Aikaeka House mospito molepi Mosquito (Culex tritaeniorhynchus), giant flies Moth fly (Telmatoscopus albipunctatus) Diptera (Diptera) insects such as,
Chicken flea Hen flea (Ceratophyllus gallinae), Japanese flea Chigoe flea (Tunga penetrans), Dog flea Dog flea (Ctenocephalides canis), Cat flea Cat flea (Ctenocephalides felis), Chicken flea Sticktight flea (Echidnopha human ritual) , Siphonaptera insects such as Oriental rat flea (Xenopsylla cheopis),
Hemiptera insects such as Bed bug (Cimex lectularius), Venezuelan sand turtle Blood-sucking bug (Rhodnius prolixus), Mexican sand turtle Kissing bug (Triatoma dimidiata), Brazilian sand turtle Kissing bug (Triatoma infestans),
Chick shaft louse (Menopon hallid) (Cuclotogaster heterographa), brown fin louse (Goniodes dissmilis), bluefin louse Fluff louse (Goniodes gallinae), large bald larvae Large hen louse (Goniodes gigas), chicken swallow louse (Duru) ), Cat louse Cat louse (Felicola subrostrata), dog lice Dog biting louse (Trichodectes canis), cattle lice Short-nosed cattle louse (Haematopinus eurysternus), cattle lice Tail switch louse (Haematopinus quadripertusus), pig louse L inus suis), buffalo louse (Haematopinus tuberculatus), dog lice Dog sucking louse (Linognathus setosus), bovine white lice Long-nosed cattle louse (Linognathus cattle louse (Haemodipsus ventricosus ), Human louse Head louse (Pediculus humanus), mouse louse Mouse louse (Polyplax serratus), pheasant Crab louse (Pthirus pubis), etc.
German cockroach (Blattella germanica), American cockroach (Periplaneta americana), Black cockroach Smoky-brown cockroach (Periplaneta fuliginosa), Japanese cockroach (Periplaneta japonica), etc.
Daikoku dry-wood termite (Cryptotermes domesticus), American white-tailed termite Western dry-wood termite (Incisitermes minor), Japanese termite Formosan subterranean termite (Coptotermes formosanus), Yamato termite Japanese subterranean termite (Reticulitermed subterrane) Isoptera insects such as termite (Odontotermes formosanus),
Butterflyfish (Arguloida) crustaceans such as butterfly (Argulus coregoni), butterfly Japanese fishlouse (Argulus japonicus), sea butterfly (Argulus scutiformis)
Sea louse (Caligus curtus, C. elongatus), Salmon rose Salmon louse (Lepeophtheirus salmonis) and other crustaceans (Siphonostomatoida) crustaceans,
Isopoda crustaceans such as Pill bug (Armadillidium vulgare), common rough woodlouse (Porcellio scaber),
Storage mite (Glycyphagus destructor), House itch mite (Glycyphagus domesticus), Cheese mite (Tyrophagus putrescentiae), House mite Feather mite (Pterolichus obtusus), Bird mite Feather mite mite (Dermatophagoides farinae), House dust mite (Dermatophagoides pteronyssinus), Cattle baboon mite Chorioptic mange mite (Chorioptes bovis), Dog ear mite (Otodectes cynotis), Cattle genus Psoroptic mite Psoropt Rabbit ear mite (Psoroptes cuniculi), Sheep scab mite (Psoroptes ovis), Dendrobus mite Itch mite (Sarcoptes scabiei), Cat mange mite (Notoedres ca ti) Astigmata mites,
Orabatida mites, such as the house salad ni (Haplochthonius simplex)
Sperm tick (Chelacaropsis moorei), cat tick (Cheyletiella blakei), rabbit tick Rabbit fur mite (Cheyletiella parasitovorax), crested tick (Cheyletiella yasguri), crested tick (Cheyletus eruditus), tick mite (Cheyletus eruditus) ), Caterpillar mites Cat follicle mite (Demodex cati), Acne mites Face mite (Demodex folliculorum), Etsurombicula wichmanni, Miyagata pine tsumutsu trombiculid mite (Helenicula miyagawai), Leptmombi ), Tsutsutsugamushi mite (Leptotrombidium scutellare) and other mites (Prostigmata) mites,
English fowl tick (Argas persicus), tick soft tick (Ornithodoros moubata), relapsing fever tick (Ornithodoros turicata), spinose ear tick (Otobius megnini), Lone star tick (Lone star tick) Amblyomma americanum, Gulf coast tick (Amblyomma maculatum), Tick tick (Haemaphysalis campanulata), Tick tick (Haemaphysalis flava), Bite tick (Haemaphysalis longicornis), Mega physic tick (Haemaphysalis longicornis) aegyptium), Mediterranean tick (Hyalomma marginatum), Tropical cattle tick (Boophilus microplus), Ixodes nipponensis, Yamato tick (Ixodes ovatus), Western black-legge d tick (Ixodes pacifcus), Schulze tick Taiga tick (Ixodes persulcatus), Sheep tick Castor bean tick (Ixodes ricinus), Black-legged tick (Ixodes scapularis), Tropical horse tick (Anocentor nitens), Rocky Mountains Rocky Mountain wood tick (Dermacentor andersoni), Pacific Coast tick (Dermacentor occidentalis), Amikemeka tick Ornate cow tick (Dermacentor reticulatus), American dog tick American dog tick (Dermacentor variabilis), Ripicentor spp. Tick American cattle tick (Rhipicephalus annulatus), Brown dog tick (Rhipicephalus sanguineus) and other ticks (Metastigmata) ticks,
Red mite (Dermanyssus gallinae), house dust mite Tropical rat mite (Ornithonyssus bacoti), avian tick mite Northern fowl mite (Ornithonyssus sylviarum) and other mites (Mesostigmata) mites,
Stylommatophora gastropods, such as the Japanese slug, Terrestrial slug (Limax marginatus), slug (Meghimatium bilineatum)
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), dog whipworm Dog whipworm (Trichuris vulpis), 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.
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 dog heartworm (Dirofilaria immitis) and the African eye worm (Loa loa),
Bald worms such as Moniliformis moniliformis, 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 Insects Dwarf equine tapeworm (Paranoplocephala mamillana), Benedenta taper Common tapeworm (Moniezia benedeni), expanded tapeworm Sheep tapeworm (Moniezia expansa), Stilsia spp.
Striated insects (Pharyngostomum cordatum), Schistosoma haematobium, Schistosoma haematobium, Schistosoma japonicum, Schistosoma japonicum, Schistosoma mansoni, etc.
Echinostoma cinetorchis, Echinostoma hortense, Giant liver fluke (Fasciola gigantica), Liver common liver fluke (Fasciola hepatica), Fasciolopsis buski, Flat belly twin Echinostomida, 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) Paragonimus miyazakii, Paragonimus ohirai, Westermann Lung fluke (Paragonimus westermani), etc. Platimorchiida
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) fluke,
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 sporophytes,
Haemoproteus mansoni, chicken leucocytozone (Leucocytozoon caulleryi), Plasmodium falciparum, Plasmodium malariae, Plasmodium ovale, Plasmodium ovale Haemosporida spores such as 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) spores,
Vestibuliferida ciliates, such as large intestine barantidium coli,
Histomanas meleagridis, Pentatrichomonas hominis, Trichomonas tenax and other Trichomonadida flagellates,
Dipromonads (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 Examples include Trypanosoma cruzi, Trypanosoma equiperdum, Trypanosoma evansi, and Kinetoplastida flagellates, among which Hymenoptera, Diptera, Coleoptera insects, Hemiptera insects, Chamiopod insects, Reticulate insects, Isoptera insects, Lepidoptera crustaceans, Chiffonotom crustaceans, Isopodal crustaceans, Conidiomyidae mites, Sasaradonia Mites, subcarids, mites, mites, spider mites The parasite and sanitary pest control agent of the present invention exerts an excellent effect on the extermination of arthropods as ectoparasites and sanitary pests belonging to the above, especially diptera such as flies and mosquitoes, Harmful invertebrates that are effective against parasitoid insects, spider mites, mite mites, and ticks, but are controlled by the parasite and sanitary pest control agents of the present invention Is not limited to these.

  When the parasite and sanitary pest control agent of the present invention is used to control these harmful invertebrates, the pyrazole derivative represented by the general formula (1) as an active ingredient or a salt thereof, or one selected from them Alternatively, a mixture of two or more kinds can be used as is, but usually mixed with an appropriate solid carrier or liquid carrier, and if desired, a surfactant, penetrant, spreading agent, thickener, antifreeze agent, binding Agent, anti-caking agent, disintegrating agent, antifoaming agent, antiseptic and anti-degradation agent, etc. added, soluble concentrate, emulsion (emulsifiable concentrate), wettable powder, water solvent (water soluble powder, water dispersible granule, water soluble granule, suspension concentrate, concentrated emulsion, suspoemulsion, microemulsion (micr) It can be formulated into any dosage form suitable for the administration route, such as oemulsion, dustable powder, granule, tablet, and emulsifiable gel, and can be put to practical use.

  When the parasite and sanitary pest control agent of the present invention is used as an animal parasite control agent, the pyrazole derivative represented by the general formula (1) as an active ingredient or a salt thereof, or one or two selected from them The mixture to be protected is a parasite control composition formulated with a carrier comprising one or more pharmaceutically or veterinarily acceptable excipients and an auxiliary suitable for the route of administration, and is to be protected. Harmful parasitic invertebrates can be effectively exterminated by direct administration to animals or by spraying the animals in an animal breeding environment such as a barn.

  When the parasite control agent of the present invention is directly administered to a target animal to be protected from harmful parasites, it can be administered using a method such as oral administration, parenteral administration or administration using a molded product. Oral administration includes, for example, drug bath or immersion, shampoo, spray, dripping (Pour-on), spotting (Spot-on) and dusting, etc., subcutaneous injection, intramuscular injection, intraperitoneal injection Or administration by injection such as intravenous injection, administration by implantation (Inplants) and the like, nasal administration and administration by suppository, etc., and as administration by molded products, neck collars (Neck collars), halters (Halters), Examples thereof include administration using a labeling device such as a tail band, a rim band, and an ear tag. Among these administration methods, oral administration and percutaneous administration such as drug bath or immersion, dripping, spotting, etc. are particularly preferable as the method for administering the parasite control agent of the present invention, but the administration method of the present invention is limited to these. It is not a thing.

  When a harmful parasitic invertebrate is controlled using the parasite control agent of the present invention, the preferable dose of the pyrazole derivative represented by the general formula (1) as an active ingredient or a salt thereof is an object to be controlled. Although it depends on the kind of parasite, the species of the subject animal to be administered or the administration method, etc., it is usually 0.01-100 mg / kg, preferably 0.01-50 mg / kg per body weight of the subject animal to be administered. It is.

  When a harmful parasitic invertebrate is controlled by administration of the parasite control agent of the present invention, the administration interval depends on the type of the target parasite to be controlled, the type of the target animal to be controlled, the administration method, and the like. However, it can usually be arbitrarily set in the range of daily to once a year, preferably once a week to once every six months, more preferably once a month to once every three months.

  Examples of the dosage form for oral administration of the parasite control agent of the present invention include tablets (Tablets), solid dosage forms (Chewables), capsules (Capsules), pills (Pills), Daimaru (Boluses), granules. Solid preparations such as Granules and Powders; Semisolid preparations such as Pastes and Gels; Liquid preparations such as Drinks and the like. For administration, for example, solid preparations such as powders (Powders); semi-solid preparations such as creams (Cream), ointments (Salve and Ointment), pastes (Pastes), gels (Gels), etc. Liquid preparations such as sprays (Spray), aerosols (Aerosols), solutions (Solutions and Emulsions), suspensions (Suspensions), lotions (Lotions), etc. Examples of molds include solutions and emulsions and suspensions (Sus liquid preparations such as pensions), and examples of dosage forms for intranasal administration include liquid preparations such as aerosols (Aerosols) and the like, which are sprayed into animal breeding environments such as barns Examples of dosage forms include solid preparations such as wettable powders, dusts and granules; liquid preparations such as emulsions and flow concentrates. Although mentioned, the formulation used for the parasite control agent of this invention is not limited only to these dosage forms.

  The solid preparation can be used orally as it is, or can be used after being diluted with water and transdermally applied or sprayed in an animal breeding environment such as a barn.

  The solid preparation used for oral administration includes a pyrazole derivative represented by the general formula (1) or a salt thereof, one or more excipients and binders suitable for oral administration, and if necessary, a lubricant. It can be prepared by mixing with a physiologically acceptable additive such as an agent, a disintegrant, a dye and a pigment, and molding the mixture into a desired shape. Examples of excipients and binders include sugars or sugar derivatives such as lactose, sucrose, mannitol, sorbitol, starches such as corn starch, wheat starch, rice starch, and potato starch, methylcellulose, carboxymethylcellulose, hydroxyethylcellulose, hydroxypropyl Cellulose or cellulose derivatives such as cellulose and hydroxypropylmethylcellulose, proteins or protein derivatives such as zein and gelatin, honey, gum arabic glue, polyvinyl alcohol, and synthetic polymer compounds such as polyvinyl pyrrolidone, etc. Examples include magnesium stearate, and examples of the disintegrant include cellulose, agar, alginic acid, cross-linked polyvinyl pyrrolidinone, and carbonate. In addition, among solid preparations used for oral administration, especially in the case of solid preparations such as chewable agents, additives that give the taste, texture and flavor of animals to be administered can also be used. The carriers and additives used in the solid preparation of the agent composition are not limited to these.

  Liquid preparations can be administered as they are, transdermally or by injection, or mixed with feed and administered orally, diluted with water and transdermally applied or sprayed in animal breeding environments such as barns. it can.

Solution, suspension used for transdermal administration, especially for the application of active compound locally to the skin of an animal and moving throughout the epithelium, further penetrating into the epithelium, and exerting a systemic control effect on the animal, etc. A liquid preparation such as an agent is composed of a pyrazole derivative represented by the general formula (1) or a salt thereof and a medium suitable for one or more local administrations, and if necessary, an absorption enhancer, a surfactant, a suspension. Add physiologically acceptable additives such as solubilizers, suspending agents, dispersants, stabilizers, spreading agents, thickeners, preservatives, antioxidants, light stabilizers and colorants, It can be prepared by dissolving, suspending or emulsifying. Suitable media for topical administration include, for example, water, ethanol, 1-propanol, 2-octyldodecanol, oleyl alcohol, benzyl alcohol, phenylethanol, phenoxyethanol, ethylene glycol, propylene glycol, polyethylene glycol, polypropylene glycol, glycerin, etc. alcohols, diethylene glycol monobutyl ether, glycol ethers such as dipropylene glycol monomethyl ether, ethyl acetate, butyl acetate, esters of benzyl benzoate, and saturated aliphatic alcohols of chain of caproic acid length C ₁₂ -C _18, hexyl laurate , Isopropyl myristate, isopropyl palmitate, decyl oleate, oleyl oleate, diisopropyl adipate, dibutyl adipate Esters such as dibutyl phthalate and diisopropyl isophthalate, amides such as N, N-dimethylacetamide and N-methylpyrrolidone, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as liquid paraffin and light liquid paraffin, Examples include aromatic hydrocarbons, DMSO (dimethyl sulfoxide), vegetable oils such as sesame oil, synthetic oils such as ethyl oleate and fatty acid triglycerides, silicone oils, and the like. Examples thereof include fatty acid esters such as glycol and fatty acid triglyceride, DMSO (dimethyl sulfoxide), and silicone oil.

  Liquid preparations such as solutions and suspensions used for administration by injection include pyrazole derivatives represented by the general formula (1) or salts thereof, lipophilic or hydrophilic media, and if necessary suspending agents, dispersions Adding physiologically acceptable additives such as solubilizers such as agents, stabilizers, buffering acids, bases or salts thereof, isotonic agents, thickeners, antioxidants and protective agents, It can be prepared by dissolving, suspending or emulsifying. Examples of the lipophilic medium include vegetable oils such as sesame oil, synthetic oils such as ethyl oleate and fatty acid triglycerides, and liposomes. Examples of the hydrophilic medium include water and propylene glycol.

Examples of the surfactant used in the liquid preparation include anionic properties such as sodium lauryl sulfate, aliphatic alcohol sulfate, monoalkyl polyglycol orthophosphate monoethanolamine salt, and dialkyl polyglycol orthophosphate monoethanolamine salt. Surfactants such as cationic surfactants such as cetyltrimethylammonium chloride, amphoteric surfactants such as disodium N-lauryl-β-iminodipropionate, lecithin, and sorbitan monostearate, monostearate Nonionic surfactants such as acid glycerin, polyoxyethyl stearate, alkylphenol polyglycol ether, etc. are mentioned, and examples of solubilizers include propylene glycol, oleic acid, polyvinylpyrrolidone Examples include polyoxyethylated castor oil, polyoxyethylated sorbitan ester, and ethylenediamine. Examples of spreading agents include chain lengths of dipropylene glycol monomethyl ether, isopropyl myristate, isopropyl palmitate, and caprylic acid. esters of saturated fatty alcohols of C ₁₂ -C _18, esters of saturated fatty alcohols of chain length _C 12 _{-C 18} of capric acid, oleic acid, ethyl oleate, fatty acid triglycerides, include, silicone oils, Examples of the buffer include phosphates, examples of the isotonic agent include sodium chloride and glycerin, and examples of the thickener include sodium carboxymethylcellulose, sorbitol, dextran, and the like. , Oxidation prevention Examples of the agent include sulfite, metabisulfite, ascorbic acid, butylhydroxytoluene, butylhydroxyanisole, and tocopherol. Examples of the preservative and protective agent include butanol, benzyl alcohol, trichlorobutanol, phenol, p. -Hydroxybenzoic acid ester etc. are mentioned, However, The medium and additive used for the liquid preparation of the parasite control agent composition of this invention are not limited only to these.

  Semi-solid preparations can be administered by applying or spreading on the skin or introducing into body cavities.

  Semi-solid preparations such as creams, ointments, pastes, gels, etc. are usually more physiologically acceptable sticking to the liquid preparations, with the aim of keeping the parasite control composition at the site of administration. Can be prepared by adding agents. Examples of the sticking agent include acacia gum, alginic acid, bentonite, cellulose, xanthan gum, colloidal magnesium aluminum silicate, and the like, but the sticking agent used in the semi-solid preparation of the parasite control agent composition of the present invention is limited to these. It is not limited.

  Next, the compounding example of the parasite control agent composition of this invention is shown. However, the compounding example of the parasite control agent composition of this invention is not limited only to these. In the following formulation examples, “parts” means parts by weight.

Solid preparation
Pyrazole derivative 0.01-80 parts Solid carrier 5-99.99 parts Surfactant 0-15 parts Others 0-5 parts Others include, for example, lubricants and disintegrants.

[Liquid preparation]
Pyrazole derivative 1-50 parts Liquid carrier 40-99 parts Surfactant 0-50 parts Others 0-10 parts Others include, for example, suspending agents, dispersing agents, stabilizers, spreading agents and the like.

  Although the formulation example of the parasitic-control agent composition of this invention is shown more specifically below, the formulation of the parasitic-control agent composition of this invention is not limited only to these.

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

[Formulation Example 1] wettable powder preparation pyrazole derivative No. 1-048 25 parts sodium diisobutylnaphthalenesulfonate 1 part calcium n-dodecylbenzenesulfonate 10 parts alkylaryl polyglycol ether 12 parts sodium naphthalenesulfonate formalin condensate Salt 3 parts Emulsion-type silicone 1 part Silicon dioxide 3 parts Kaolin 45 parts [Formulation Example 2] Water-soluble thickener preparation pyrazole derivative No.1-048 20 parts Polyoxyethylene lauryl ether 3 parts Sodium dioctyl sulfosuccinate 3.5 parts Dimethyl sulfoxide 37 parts 2-propanol 36.5 parts [Formulation example 3] Spray solution pyrazole derivative No. 1-048 2 parts dimethyl sulfoxide 10 parts 2-propanol 35 parts acetone 53 parts [Formulation example 4] liquid for transdermal administration Pyrazole Conductor No. 1-048 5 parts Hexylene glycol 50 parts Isopropanol 45 parts [Formulation example 5] Solution pyrazole derivative No. 1-048 for transdermal administration 50 parts propylene glycol monomethyl ether 50 parts Dipropylene glycol 45 parts [Formulation example 6 ] Percutaneous administration (drip) solution pyrazole derivative No.1-048 2 parts light liquid paraffin 98 parts [Formulation example 7] Transdermal administration (drip) solution pyrazole derivative No.1-048 2 parts light liquid paraffin 58 parts Olive oil 30 parts ODO-H 9 parts Shin-Etsu Silicone 1 part In the parasite control method of the present invention, an effective amount of a pyrazole derivative represented by the general formula (1) or a salt thereof is administered alone as an active ingredient. It can also be mixed with other insecticides, acaricides, anthelmintics, antibacterial agents, etc., as necessary, at the time of formulation or administration. .

  By mixing with other insecticides, acaricides, anthelmintics, or antibacterial agents, etc., the control spectrum can be expanded by the additive / synergistic effects of the mixed drugs, the parasite control effect can be improved, and the dosage It can be expected to reduce the cost of controlling parasites by reducing the amount of worms, and to maintain the effect of controlling parasites over a longer period of time. In particular, administration by mixing with other types of insecticides, acaricides, and anthelmintic agents having different mechanisms of action is an extremely effective control method from the viewpoint of preventing drug resistance from being acquired by parasites. At this time, a combination of a plurality of known insecticides, known acaricides, known anthelmintic agents or known antibacterial agents is also possible.

  Specific examples of the general names of insecticides, acaricides, anthelmintics or antibacterials that can be used in combination with the pyrazole derivatives represented by the general formula (1) are as follows. It is not limited to only.

  Nematicides: aldoxycarb, cadusafos, DCP, DBCH, dichlofenthion, DSP (DSP), etoprophos, fenamiphos, fensulfothion, fluene Sulfone (fluensulfone), fosthiazate (fosthiazate), fosthietan (fosthietan), imisiafos (imicyafos), isamidofos (isamidofos), isazofos (isazofos), oxamyl (oxamyl) and thionazin (thionazin) and the like.

  Acaricide: acequinocyl, acrinathrin, amitraz, BCI-033 (test name), bifenazate, bromopropylate, chinomethionat, chlorobezilate , Clofentezine, cyenopyrafen, cyflumetofen, cyhexatine, dicofol, dienochlor, denochlor (DNOC), etoxazole, quinazaquin (fenaza) Fenbutatin oxide, fenothiocarb, fenpropathrin, fenpyroximate, fluacrypyrim, halfenprox (halfenpro) x), hexythiazox, milbemectin, propargite, pyridaben, pyrimidifen, S-1870 (test name), spirodiclofen, spiromesifen ( spyromesifen), NNI-0711 (test name), CL900187 (test name) and tebufenpyrad.

  Insecticides: abamectin, acephate, acetamipirid, alanamicarb, aldicarb, allethrin, azamethiphos, azinphos-methyl, bacillus tubulin Bacillus thuringiensis, bendiocarb, benfluthrin, benfuracarb, bensultap, bifenthrin, bioallethrin, bioresmethrin, bistrifluron, tris Buprofezin, butocarboxim, carbaryl, carbofuran, carbosulfan, cartap, chlorantraniliprole, Chlorethxyfos, chlorfenapyr, chlorfenvinphos, chlorfluazuron, chlormephos, chlorpyrifos, chlorpyrifos-methyl, chromafenozide, chromafenozide Clothianidin, cyantraniliprole, cycloprothrin, cyflumetofen, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin cyhalothrin), cypermethrin, alpha-cypermethrin, beta-cypermethrin, zeta-cypermethrin, cyromazine, Deltamethrin, diacloden, diafenthiuron, diazinon, dichlorvos, diflubenzuron, dimethylvinphos, dinotefuran, diofenolan, diofenolan Disulfoton, dimethoate, emamectin-benzoate, empenthrin, endosulfan, alpha-endosulfan, EP-N, EPN, esfenvalerate, etiophencarb (Ethiofencarb), ethiprole, etofenprox, etrimfos, fenitrothion, fenobucarb, fenobucarb Fenoxycarb, fenpropathrin, fenthion, fenvalerate, fipronil, flonicamid, flubendiamide, flucythrinate, flufenerim , Flufenoxuron, flufenprox, flumethrin, fluvalinate, tau-fluvalinate, fonophos, formetanate, formotaion ( formothion), furathiocarb, flufiprole, flupyradifurone, flometoquin and the like.

  Insecticides (continued): halofenozide, hexaflumuron, hydramethylnon, imidacloprid, isofenphos, indoxacarb, isoprocarb, isoxathion ), Lepimectin, lufenuron, malathion, meperfluthrin, metaflumizone, metalaldehyde, methamidophos, methidathion, methidathion, methacrifos (methacrifos) ), Metalcarb, methomyl, metoprene, methoxychlor, methoxyfenozide, methyl bromide , Monocrotophos, muscalure, nitenpyram, novaluron, noviflumuron, omethoate, oxamyl, oxydemeton-methyl, oxydemeton-methyl (oxydemeton-methyl) oxydeprofos, parathion, parathion-methyl, pentachlorophenol (PCP), permethrin, phenothrin, phenthoate, phoxim, phorate ), Phosalone, phosmet, phosphamidon, pirimicarb, pirimiphos-methyl, profenofos, prothiofos, propaphos, prototri Protrifenbute, pyrometrozine, pyraclofos, pyrethrins, pyridalalyl, pyrifluquinazon, pyriprole, pyrafluprole, proxy, pyrifiprofen, py Resmethrin, rotenone, SI-0405 (study name), sulprofos, silafluofen, spinetram, spinosad, spirotetramat, sulfoxaflor ), Sulfotep, SYJ-159 (test name), tebfenozide, teflubenzuron, tefluthorin, terbufos, tetrachlorvinphos, tetrame Trimethrin, dT-80-phthalthrin, d-tetramethrin, tetramethylfluthrin, thiacloprid, thiocyclam, thiodicarb, thiamethoxam, thiophanox ( thiofanox, thiometon, tolfenpyrad, tralomethrin, trichlorfon, triazuron, triflumuron, vamidomion and ME-5343 (test name).

  Anthelmintic: acriflavine, albendazole, atovaguone, azithromycin, bithionol, bromofenofos, carnidazole, chloroquine, clazuril ), Clindamycin hydrochloride, clorsulon, closantel, coumaphos, cymiazol, dichlorophen, dichlorophen, diethylcarbamazine, diminazene, disophenol (Disophenol), dithiazanine iodide, doxycycline hydrochloride, doramectin, emodepside, eprinomectin, febantel, febantel Fenbendazole, flubendazole, furazolidone, furazolidone, glycalpyramide, imidocarb, ivermectin, levamisole, mebendazole, mefloquine, mefloquine Hydrochloride (melarsamine hydrochloride), metronidazole, metyridine, milbemycine oxime, monepantel, morantel tartrate, moxidectin, nicarbazin, los amide , Nitroxynil, oxybendazole, oxyclozanide, pamaquine, phenothiazine, pipette adipate Piperazineadipate, piperazine citrate, piperazine phosphate, praziquantel, primaquine, propetamphos, propoxur, pyrantel pamoate, pyrantel pamoate pyrimethamine, santonin, selamectin, sulfadimethoxine, sulfadoxine, sulfamerazine, sulfamonomethoxine, sulfamoildapsone, tinidazole ), Toltrazuril, tribromsalan and triclabendazole.

  Antibacterial agents: amoxicillin, ampicillin, cefapirin, cefazolin, cefquinome, cefquinofur, chlortetracycline, clavulaniccin, clavulanic acid ), Difloxacin, diitolmide, enrofloxacin, florfenicol, lincomycin, lomefloxacin, marbofloxacin, miloxacin , Mirosamycin, norfloxacin, ofloxacin, orbifloxacin, oxolinic acid, oxytetracycline, pe Penicillin, thiamphenicol, tiamulinfumarate, tilmicosin phosphate, acetylisovaleryltylosin acetate, tylosin phosphate, tulathromycin And valnemulin.

  Antifungal agents: ketoconazole, miconazole nitrate, etc.

  In the following, the present invention will be described in more detail by specifically describing, as examples, synthesis examples and test examples of pyrazole derivatives represented by the general formula (1), which are active ingredients of the parasite control agent of the present invention. However, the present invention is not limited to these.

[Synthesis example]
Synthesis example 1
Production of 3′-methyl-1 ′-(pyridin-3-yl) -1- (2,2,2-trifluoroethyl) -1H, 1′H-3,4′-bipyrazole (pyrazole derivative 1-001 )
Process 1
Preparation of 1- {3-methyl-1- (pyridin-3-yl) -1H-pyrazol-4-yl} ethanone To a solution of 12.6 g of 3-iodopyridine in 100 ml of N, N-dimethylformamide, 1- (3 -Methyl-1H-pyrazol-4-yl) ethanone 7.08 g in N, N-dimethylformamide in 20 ml and cesium carbonate 46.3 g were added. After replacing the inside of the reaction vessel with nitrogen gas, 2.3 g of copper iodide (monovalent) was added and stirred at room temperature for 30 minutes. After completion of stirring, stirring was continued at 120 ° C. for 15 hours. After completion of the reaction, the reaction mixture was allowed to cool to room temperature. Insoluble matter precipitated in the reaction mixture after being allowed to cool was removed by Celite filtration under reduced pressure, and 200 ml of ethyl acetate was added to the filtrate. The obtained organic layer was washed and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. Medium-pressure preparative liquid chromatography (Yamazen) eluting the residue obtained after distilling off the solvent with n-hexane-ethyl acetate [gradient of 1: 1 to 1: 9 (volume ratio, hereinafter the same)] The product was purified with a medium pressure fractionator (YFLC-Wprep) to obtain 7.8 g of the target product as a white solid.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 8.98 (d, J = 3.3 Hz, 1H), 8.60 (d, J = 4.8 Hz, 1H), 8.33 (s, 1H ), 8.05-8.10 (m, 1H), 7.43 (dd, J = 4.8, 8.4 Hz, 1H), 2.58 (s, 3H), 2.50 (s, 3H) ).

Process 2
Preparation of 3- (dimethylamino) -1- {3-methyl-1- (pyridin-3-yl) -1H-pyrazol-4-yl} propen-2-en-1-one 1- {3-methyl- 1-g of t-butoxybis (dimethylamino) methane was added to 7.7 g of 1- (pyridin-3-yl) -1H-pyrazol-4-yl} ethanone, and the mixture was stirred at 60 ° C. for 1 hour. After completion of the reaction, 5 ml of diisopropyl ether was added to the reaction mixture. After the addition, the solid precipitated in the reaction mixture was removed by filtration to obtain 7.9 g of the desired product as a pale yellow solid.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 8.98 (d, J = 3.3 Hz, 1H), 8.56 (d, J = 4.8 Hz, 1H), 8.27 (s, 1H ), 8.00-8.10 (m, 1H), 7.77 (d, J = 18.0 Hz, 1H), 7.42 (dd, J = 4.8, 8.4 Hz, 1H), 5 .47 (d, J = 18.0 Hz, 1H), 3.05 (brs, 6H), 2.61 (s, 3H).

Process 3
Preparation of 3′-methyl-1 ′-(pyridin-3-yl) -1H, 1′H-3,4′-bipyrazole 3- (Dimethylamino) -1- {3-methyl-1- (pyridine-3 -Yl) -1H-pyrazol-4-yl} propen-2-en-1-one To a solution of 7.9 g of ethanol in 25 ml of ethanol was added 1.7 g of hydrazine monohydrate, and the mixture was stirred under ethanol reflux for 1 hour. did. After completion of the reaction, about half of the solvent was distilled off under reduced pressure, and 5 ml of diisopropyl ether was added. After the addition, the solid precipitated in the reaction mixture was taken out by filtration to obtain 6.2 g of the desired product as a white solid.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 9.00 (d, J = 3.3 Hz, 1H), 8.53 (d, J = 4.8 Hz, 1H), 8.20 (s, 1H ), 8.00-8.10 (m, 1H), 7.66 (d, J = 1.8 Hz, 1H), 7.40 (dd, J = 4.8, 8.4 Hz, 1H), 6 .51 (d, J = 1.8 Hz, 1H), 2.58 (s, 3H), (proton peak corresponding to NH was not detected).

Process 4
Production of 3′-methyl-1 ′-(pyridin-3-yl) -1- (2,2,2-trifluoroethyl) -1H, 1′H-3,4′-bipyrazole 60% by weight sodium hydride (Dispersed in mineral oil) 3'-methyl-1 '-(pyridin-3-yl) -1H, 1'H-3,4'- was added to a solution of 404 mg of N, N-dimethylformamide in 10 ml under ice cooling. A solution of 1.9 g of bipyrazole in 5 ml of N, N-dimethylformamide was gradually added and stirred for 30 minutes. After completion of the stirring, 2.97 g of 2,2,2-trifluoroethyl trifluoromethanesulfonic acid was added and stirred at the same temperature for 2 hours. After completion of the reaction, 30 ml of ethyl acetate and 30 ml of water were added, and the organic layer was separated. The obtained organic layer was dehydrated and dried in the order of water, saturated brine and then anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography (Yamazen Corporation medium pressure preparative device; YFLC-Wprep) eluting with n-hexane-ethyl acetate (gradient of 1: 1 to 1: 9). did. Further, crystallization was performed with 25 ml of ethyl acetate to obtain 2.4 g of the desired product as a white solid.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 9.00 (d, J = 3.3 Hz, 1H), 8.52 (d, J = 4.8 Hz, 1H), 8.21 (s, 1H ), 8.00-8.10 (m, 1H), 7.55 (d, J = 1.8 Hz, 1H), 7.40 (dd, J = 4.8, 8.4 Hz, 1H), 6 .51 (d, J = 1.8 Hz, 1H), 4.75 (q, J = 9.3 Hz, 2H), 2.57 (s, 3H).

Synthesis example 2
Production of 3′-methyl-1 ′-(pyridin-3-yl) -1- (pyridin-4-yl) -1H, 1′H-3,4′-bipyrazole (pyrazole derivative 1-018)
To a 2 ml solution of 3′-methyl-1 ′-(pyridin-3-yl) -1H, 1′H-3,4′-bipyrazole in 200 ml of dimethyl sulfoxide was added 259 mg of 4-bromopyridine hydrochloride and 667 mg of cesium carbonate. . After replacing the inside of the reaction vessel with nitrogen gas, 51 mg of copper iodide (monovalent) was added and stirred at room temperature for 30 minutes. After completion of the stirring, stirring was continued at 130 ° C. for 10 hours. After completion of the reaction, the reaction mixture was allowed to cool to room temperature. The insoluble matter precipitated in the reaction mixture after being allowed to cool was removed by Celite filtration under reduced pressure, and 5 ml of ethyl acetate was added to the filtrate. The obtained organic layer was washed and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The solid precipitated after distilling off the solvent was washed with diisopropyl ether to obtain 173 mg of the desired product as a white solid.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 9.00-9.10 (m, 1H), 8.67 (d, J = 6.0 Hz, 2H), 8.50-8.60 (m , 1H), 8.29 (s, 1H), 8.08 (d, J = 1.8 Hz, 1H), 8.05-8.15 (m, 1H), 7.69 (d, J = 6) 0.0 Hz, 2H), 7.41 (dd, J = 4.8, 8.4 Hz, 1H), 6.70 (d, J = 1.8 Hz, 1H), 2.66 (s, 3H).

Synthesis example 3
Preparation of 2- {1- (pyridin-3-yl) -1H-pyrazol-4-yl} -5- (trifluoromethyl) pyridine (pyrazole derivative 9-001)
Process 1
Preparation of 3- (4-iodo-1H-pyrazol-1-yl) pyridine 3- (1H-pyrazol-1-yl) pyridine (5 g) in acetonitrile (100 ml) at room temperature with 8.14 g of N-iodosuccinimide and trifluoroacetic acid 5 ml was sequentially added and stirred at the same temperature for 15 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. To the obtained residue, 100 ml of 2N aqueous sodium hydroxide solution was added. After completion of the addition, the solid precipitated in the reaction mixture was removed by filtration to obtain 10.5 g of the desired product as a pale yellow solid.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 8.97 (d, J = 2.4 Hz, 1H), 8.57 (dd, J = 1.5, 4.8 Hz, 1H), 8.05 −8.15 (m, 1H), 8.02 (s, 1H), 7.78 (s, 1H), 7.46 (dd, J = 4.8, 8.1 Hz, 1H).

Process 2
Preparation of 3- {4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-pyrazol-1-yl} pyridine 3- (4-Iodo-1H -Pyrazol-1-yl) pyridine in a solution of 5 g of dimethyl sulfoxide in 5.6 g of bispinacolatodiborane, 6.1 g of potassium acetate and PdCl ₂ (dppf) ₂ {[1,1′-bis (diphenylphosphino) ferrocene ] 0.75 g of palladium (divalent) chloride} was sequentially added. The reaction vessel was replaced with nitrogen gas, followed by stirring at 120 ° C. for 3.5 hours. After completion of the reaction, 100 ml of water was added to the reaction solution and extracted with ethyl acetate (200 ml × 1). The obtained organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography eluting with n-hexane-ethyl acetate 1: 1 to obtain 3.0 g of the desired product as a brown resin.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 9.01 (d, J = 2.7 Hz, 1H), 8.56 (dd, J = 1.5, 4.5 Hz, 1H), 8.27 (S, 1H), 8.00-8.10 (m, 1H), 8.01 (s, 1H), 7.41 (ddd, J = 0.6, 4.8, 8.4 Hz, 1H) , 1.35 (s, 12H).

Process 3
Preparation of 2- {1- (pyridin-3-yl) -1H-pyrazol-4-yl} -5- (trifluoromethyl) pyridine 3- {4- (4,4,5,5, -tetramethyl- 1,3,2-dioxaborolan-2-yl) -1H-pyrazol-1-yl} pyridine (400 mg) in 1,2-dimethoxyethane 20 ml solution, 2-bromo-5-trifluoromethylpyridine 367 mg, potassium carbonate 511 mg, 5 ml of water and 50 mg of [1,1′-bis (diphenylphosphino) ferrocene] palladium (II) dichloride dichloromethane adduct were sequentially added and stirred at 80 ° C. for 3 hours. After completion of the reaction, 30 ml of water was added and extracted with ethyl acetate (50 ml × 1). The obtained organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography eluting with ethyl acetate to obtain 190 mg of the desired product as a white solid.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 9.09 (d, J = 2.7 Hz, 1H), 9.00 (d, J = 2.4 Hz, 1H), 8.86 (brs, 1H ), 8.61 (s, 1H), 8.26 (s, 1H), 8.13 (ddd, J = 1.5, 2.7, 8.4 Hz, 1H), 7.90-8.00. (M, 1H), 7.66 (d, J = 8.4 Hz, 1H), 7.45-7.50 (m, 1H).
Melting point 163-164 [deg.] C.

Synthesis example 4
Production of 3- [4- {4- (trifluoromethyl) phenyl} -1H-pyrazol-1-yl] pyridine (pyrazole derivative 6-001)
To a solution of 300 mg of 3- (4-iodo-1H-pyrazol-1-yl) pyridine in 20 ml of 1,2-dimethoxyethane, 500 mg of 4-trifluoromethylphenylboronic acid, 300 mg of potassium carbonate, 5 ml of water and PdCl ₂ (dppf) ₂ 90 mg was sequentially added and stirred at 80 ° C. for 3 hours. After completion of the reaction, 30 ml of water was added and extracted with ethyl acetate (50 ml × 1). The obtained organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography eluting with n-hexane-ethyl acetate 1: 1 to obtain 150 mg of the desired product as a pale red solid.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 9.06 (d, J = 2.4 Hz, 1H), 8.61 (dd, J = 1.5, 4.8 Hz, 1H), 8.26 (S, 1H), 8.05-8.15 (m, 1H), 8.09 (s, 1H), 7.67 (s, 4H), 7.46 (dd, J = 4.8, 8 .1Hz, 1H).
Mp 141-144 ° C.

Synthesis example 5
7- (Pyridin-3-yl) -2- (2,2,2-trifluoroethyl) -2,4,5,7-tetrahydropyrazolo [3,4-e] indazole and 7- (Pyridine -3-yl) -1- (2,2,2-trifluoroethyl) -1,4,5,7-tetrahydropyrazolo [3,4-e] indazole (pyrazole derivatives 7-001 and Pyrazole derivative 8-001)
Process 1
Preparation of 2- (pyridin-3-yl) -6,7-dihydro-2H-indazol-4 (5H) -one To a solution of 11.9 g of 3-iodopyridine in 80 ml of N, N-dimethylformamide, 5.2 g of 7-dihydro-1H-indazol-4 (5H) -one and 29.0 g of cesium carbonate were added. After replacing the inside of the reaction vessel with nitrogen gas, 1.5 g of copper iodide (monovalent) was added and stirred at room temperature for 30 minutes. After completion of stirring, stirring was continued at 120 ° C. for 15 hours. After completion of the reaction, the reaction mixture was allowed to cool to room temperature. After standing to cool, insoluble matter precipitated in the reaction mixture was removed by Celite filtration, and 200 ml of ethyl acetate was added to the filtrate. The obtained organic layer was washed and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography eluting with n-hexane-ethyl acetate 1: 1 to obtain 2.1 g of the desired product as a white solid.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 9.00 (d, J = 2.4 Hz, 1H), 8.61 (dd, J = 1.8, 4.8 Hz, 1H), 8.38 (S, 1H), 8.03 (ddd, J = 1.8, 2.4, 8.1 Hz, 1H), 7.43 (dd, J = 4.8, 8.1 Hz, 1H), 2. 95 (t, J = 6.6 Hz, 2H), 2.57 (dd, J = 6.3, 6.9 Hz, 2H), 2.19 (dtd, J = 6.3, 6.6, 6. 9Hz, 2H).

Process 2
Preparation of 5-{(dimethylamino) methylene} 2- (pyridin-3-yl) -6,7-dihydro-2H-indazol-4 (5H) -one 2- (Pyridin-3-yl) -6 , 7-dihydro-2H-indazol-4 (5H) -one To a solution of 1.0 g of N, N-dimethylformamide in 5 ml was added 0.98 g of t-butoxybis (dimethylamino) methane, and the mixture was stirred at room temperature. Stir overnight. After completion of stirring, 0.98 g of t-butoxybis (dimethylamino) methane was added, and stirring was continued overnight at room temperature. After completion of the reaction, the solvent was distilled off under reduced pressure. The obtained solid was washed with diisopropyl ether to obtain 1.1 g of the desired product as a pink solid.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 9.03-8.99 (m, 1H), 8.55 (dd, J = 1.2, 4.8 Hz, 1H), 8.35 (s , 1H), 8.01 (ddd, J = 1.2, 2.7, 8.1 Hz, 1H), 7.60 (s, 1H), 7.40 (ddd, J = 0.6, 4. 8, 8.1 Hz, 1H), 3.14 (s, 6H), 3.03 (t, J = 7.2 Hz, 2H), 2.90 (t, J = 7.2 Hz, 2H).

Process 3
7- (Pyridin-3-yl) -2- (2,2,2-trifluoroethyl) -2,4,5,7-tetrahydropyrazolo [3,4-e] indazole and 7- (Pyridine Preparation of -3-yl) -1- (2,2,2-trifluoroethyl) -1,4,5,7-tetrahydropyrazolo [3,4-e] indazole 5-{(dimethylamino) Methylene} -2- (pyridin-3-yl) -6,7-dihydro-2H-indazol-4 (5H) -one 0.20 g of hydrazine monohydrate was added to a solution of 1.1 g of ethanol in 10 ml of ethanol. And stirred for 2 hours under ethanol reflux. After completion of the reaction, the solvent was distilled off under reduced pressure. The obtained residue was dissolved in 5 ml of N, N-dimethylformamide, and 305 mg of 60 wt% sodium hydride (dispersed in mineral oil) was added to the reaction solution at 0 ° C. After completion of the addition, the mixture was warmed to room temperature and stirred at the same temperature for 30 minutes. Then, 2.97 g of 2,2,2-trifluoroethyl trifluoromethanesulfonate was added to the reaction solution, and the mixture was stirred at the same temperature for 2 hours. Stir. After completion of the reaction, 20 ml of ethyl acetate and 20 ml of water were added to the reaction mixture, and the organic layer was separated. The obtained organic layer was dehydrated and dried in the order of water, saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography (Yamazen Corporation medium pressure preparative device; YFLC-Wprep) eluting with n-hexane-ethyl acetate (gradient of 1: 1 to 1: 3). 7- (pyridin-3-yl) -2- (2,2,2-trifluoroethyl) -2,4,5,7-tetrahydropyrazolo [3,4-e] indazole 99.5 mg A white solid (melting point: 216-218 ° C.) and 7- (pyridin-3-yl) -1- (2,2,2-trifluoroethyl) -1,4,5,7-tetrahydropyrazolo [3 , 4-e] Indazole 15.6 mg (melting point: 123-132 ° C.) of a white solid was obtained.

Synthesis Example 6
Preparation of 3- {3′-methyl-1- (2,2,2-trifluoroethyl) -1H, 1′H-3,4′-bipyrazol-1′-yl} pyridine 1-oxide (pyrazole derivative 17 -001)
To a solution of 140 mg of 3′-methyl-1 ′-(pyridin-3-yl) -1- (2,2,2-trifluoroethyl) -1H, 1′H-3,4′-bipyrazole in 3 ml of dichloromethane was added 65%. 96 mg of wt% metachloroperbenzoic acid (containing 35 wt% metachlorobenzoic acid) was added and stirred at room temperature for 1 hour. After completion of the reaction, 5 ml of a saturated aqueous sodium sulfite solution was added to the reaction mixture, and the mixture was extracted with chloroform (5 ml × 3). The obtained organic layer was dehydrated and dried in the order of water, saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography (Yamazen Corporation medium pressure preparative device; YFLC-Wprep) eluting with chloroform-methanol (99: 1 to 9: 1 gradient), 80 mg of the desired product was obtained as a white solid.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 8.72 (t, J = 1.5 Hz, 1H), 8.11 (s, 1H), 8.08 (dd, J = 1.5, 6 .0Hz, 1H), 7.50-7.65 (m, 2H), 7.31 (dd, J = 4.8, 8.4Hz, 1H), 6.50 (d, J = 1.6Hz, 1H), 4.74 (q, J = 8.4 Hz, 2H), 2.53 (s, 3H).

Synthesis example 7
Preparation of 3- {3-methyl-1- (pyridin-3-yl) -1H-pyrazol-4-yl} -5- (methylthio) isoxazole (pyrazole derivative 21-001)
Process 1
Preparation of 1- {3-methyl-1- (pyridin-3-yl) -1H-pyrazol-4-yl} -3,3-bis (methylthio) -2-propen-1-one 1- {3-methyl To a solution of 0.2 g of -1- (pyridin-3-yl) -1H-pyrazol-4-yl} ethanone in 10 ml of tetrahydrofuran was added 80 mg of carbon disulfide at room temperature. After completion of the addition, the reaction solution was cooled to 0 ° C., and 5 ml of a 60 wt% sodium hydride (dispersed in mineral oil) 80 mg tetrahydrofuran suspension was added dropwise. After completion of the dropwise addition, the temperature was raised to 50 ° C. and stirred at the same temperature for 2 hours. After completion of the stirring, the reaction solution was cooled to room temperature, 0.3 g of methyl iodide was appropriately applied, and stirring was continued at room temperature for 3 days. After completion of the reaction, 30 ml of water was added to the reaction mixture and extracted with ethyl acetate (50 ml × 1). The obtained organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue obtained after evaporation of the solvent was purified by silica gel column chromatography eluting with n-hexane-ethyl acetate 4: 6 to obtain 0.9 g of the objective product as a pale yellow solid.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 8.98 (d, J = 2.4 Hz, 1H), 8.58 (dd, J = 1.5 Hz, 4.5 Hz, 1H), 8.29 (S, 1H), 8.00-8.10 (m, 1H), 7.42 (ddd, J = 0.6, 4.8, 8.1 Hz, 1H), 6.47 (s, 1H) , 2.64 (s, 3H), 2.56 (s, 3H), 2.53 (s, 3H).

Process 2
Preparation of 3- {3-methyl-1- (pyridin-3-yl) -1H-pyrazol-4-yl} -5- (methylthio) isoxazole 247 mg of hydroxylamine hydrochloride was added to a solution of 289 mg of sodium methoxide in 5 ml of methanol. Added portionwise, and further 1- {3-methyl-1- (pyridin-3-yl) -1H-pyrazol-4-yl} -3,3-bis (methylthio) -2-propen-1-one 272 mg Then, the mixture was stirred for 7 hours at methanol reflux. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, 5 ml of water was added, and the mixture was extracted with ethyl acetate (5 ml × 3). The obtained organic layer was washed and dried in the order of water, saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography (Yamazen Corporation medium pressure preparative device; YFLC-Wprep) eluting with n-hexane-ethyl acetate (gradient of 1: 3 to 1: 9). As a result, 91 mg of the desired product was obtained as a white solid.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 8.99 (d, J = 2.7 Hz, 1H), 8.56 (dd, J = 1.5, 4.8 Hz, 1H), 8.24 (S, 1H), 8.00-8.10 (m, 1H), 7.42 (dd, J = 4.8, 8.4 Hz, 1H), 6.27 (s, 1H), 2.64. (S, 3H), 2.57 (s, 3H).

Synthesis example 8
Preparation of 5- (3-methyl-1- (pyridin-3-yl) -1H-pyrazol-4-yl) -3- (methylthiomethyl) -1,2,4-oxadiazole (pyrazole derivative 22-001) )
Process 1
Preparation of N ′-(3-methyl-1- (pyridin-3-yl) -1H-pyrazole-4-carbonyloxy) -2- (methylthio) acetimidoamide 3-methyl-1- (pyridin-3-yl ) -1H-pyrazole-4-carboxylic acid In a suspension of 400 mg of N, N-dimethylformamide hydrochloride 400 mg, 284 mg of N′-hydroxy-2- (methylthio) acetimidamide, 997 mg of triethylamine, 1-ethyl-3 566 mg of-(3-dimethylaminopropyl) carbodiimide hydrochloride and 10 mg of 1-hydroxybenzotriazole were sequentially added and stirred overnight at room temperature. After completion of the reaction, 5 ml of water was added and extracted with ethyl acetate (5 ml × 3). The obtained organic layer was washed and dried in the order of water, saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography (Yamazen Corporation medium pressure preparative device; YFLC-Wprep) eluting with n-hexane-ethyl acetate (gradient of 1: 3 to 1: 9). Thus, 350 mg of the desired product was obtained as a white solid.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 8.98 (d, J = 3.0 Hz, 1H), 8.60 (d, J = 3.9 Hz, 1H), 8.46 (s, 1H ), 8.00-8.10 (m, 1H), 7.43 (dd, J = 4.8, 8.4 Hz, 1H), 5.22 (brs, 2H), 3.36 (s, 2H) ), 2.61 (s, 3H), 2.14 (s, 3H).

Process 2
Preparation of 5- (3-methyl-1- (pyridin-3-yl) -1H-pyrazol-4-yl) -3- (methylthiomethyl) -1,2,4-oxadiazole N ′-(3- Methyl-1- (pyridin-3-yl) -1H-pyrazole-4-carbonyloxy) -2- (methylthio) acetimidoamide 3 ml of tetrabutylammonium fluoride (1M tetrahydrofuran solution) was added to 1 ml of tetrahydrofuran. And stirred at room temperature for 15 hours. After completion of the reaction, 5 ml of water was added and extracted with ethyl acetate (5 ml × 3). The obtained 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 obtained residue was purified by medium pressure preparative liquid chromatography (Yamazen Corporation medium pressure preparative device; YFLC-Wprep) eluting with n-hexane-ethyl acetate (gradient of 1: 3 to 1: 9). As a result, 243 mg of the desired product was obtained as a white solid.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 9.02 (d, J = 2.4 Hz, 1H), 8.62 (d, J = 1.5 Hz, 1H), 8.61 (s, 1H ), 8.05-8.15 (m, 1H), 7.45 (dd, J = 4.8, 8.4 Hz, 1H), 3.77 (s, 2H), 2.69 (s, 3H) ), 2.22 (s, 3H).

Synthesis Example 9
Preparation of 8- (pyridin-3-yl) -2- (pyrimidin-2-yl) -6,8-dihydro-5H-pyrazolo [3,4-h] quinazoline (pyrazole derivative 16-001)
5-{(Dimethylamino) methylene} -2- (pyridin-3-yl) -6,7-dihydro-2H-indazol-4 (5H) -one In an ethanol solution of 300 mg, sodium ethoxide (30 wt. % Ethanol solution) 0.5 ml and pyrimidine-2-carboxyimidamide hydrochloride 195 mg were sequentially added and stirred at 70 ° C. for 24 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. To the obtained residue, 5 ml of water and 5 ml of saturated brine were added, and extracted with chloroform (5 ml × 3). The obtained organic layer was dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained solid was washed with ethyl acetate to obtain 154 mg of the desired product as a pale yellow solid.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 9.07 (d, J = 2.7 Hz, 1H), 9.04 (d, J = 5.1 Hz, 2H), 8.80 (s, 1H ), 8.80 (s, 1H), 8.59 (dd, J = 1.5, 4.8 Hz, 1H), 8.08 (ddd, 1.2, 2.7, 8.4 Hz, 1H) 7.46 (d, J = 4.8 Hz, 1H), 7.44 (dd, J = 4.8, 4.8 Hz, 1H), 3.22-3.11 (m, 4H).

Synthesis Example 10
Preparation of 5- (methylthiomethyl) -3- {1- (pyridin-3-yl) -1H-pyrazol-4-yl} -4,5-dihydroisoxazole (pyrazole derivative 18-001)
Process 1
Preparation of 1- (pyridin-3-yl) -1H-pyrazol-4-aldehyde 3- (4-iodo-1H-pyrazol-1-yl) pyridine (3.0 g) in a 30 ml tetrahydrofuran solution at 0 ° C. under a nitrogen atmosphere Then, 14 ml of 1M ethylmagnesium bromide tetrahydrofuran solution was added dropwise. After stirring at the same temperature for 1 hour, 1.2 g of N, N-dimethylformamide was added. After completion of the addition, the temperature was raised to room temperature, and stirring was continued for 15 hours at the same temperature. After completion of the reaction, 50 ml of water was added and extracted with ethyl acetate (100 ml × 1). The obtained organic layer was dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue obtained after distilling off the solvent was purified by silica gel column chromatography eluting with n-hexane-ethyl acetate 4: 6 to obtain 0.6 g of the desired product as a white solid.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ10.01 (s, 1H), 9.04 (d, J = 2.8 Hz, 1H), 8.66 (dd, J = 1.5, 4 .8 Hz, 1H), 8.50 (s, 1H), 8.23 (s, 1H), 8.05-8.15 (m, 1H), 7.48 (dd, J = 4.8, 8 .1Hz, 1H).

Process 2
Preparation of 5- (methylthiomethyl) -3- {1- (pyridin-3-yl) -1H-pyrazol-4-yl} -4,5-dihydroisoxazole 1- (Pyridin-3-yl) -1H -To a solution of 300 mg of pyrazole-4-aldehyde in 10 ml of methanol was added a solution of 130 mg of hydroxylamine hydrochloride in 3 ml of water at room temperature. After completion of the addition, the reaction solution was stirred at 60 ° C. for 2 hours, and then the solvent was distilled off under reduced pressure. To the residue obtained after distilling off the solvent, 10 ml of N, N-dimethylformamide and 290 mg of N-chlorosuccinimide were added and stirred at 75 ° C. for 2 hours. After completion of the stirring, the reaction solution was cooled to room temperature, 300 mg of allyl methyl sulfide, 1 g of potassium hydrogen carbonate and 0.5 ml of water were sequentially added, and stirring was continued at room temperature for 15 hours. After completion of the reaction, 30 ml of water was added and extracted with ethyl acetate (50 ml × 1). The obtained organic layer was dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue obtained after distilling off the solvent was purified by silica gel column chromatography eluting with n-hexane-ethyl acetate 3: 7 to obtain 0.24 g of the desired product as a white solid.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 9.02 (d, J = 2.7 Hz, 1H), 8.60 (d, J = 4.8 Hz, 1H), 8.28 (s, 1H ), 8.05-8.15 (m, 1H), 8.02 (s, 1H), 7.42 (ddd, J = 0.6, 4.8, 8.1 Hz, 1H), 4.85. -5.00 (m, 1H), 3.44 (dd, J = 10.2, 16.8 Hz, 1H), 3.25 (dd, J = 8.1, 17.7 Hz, 1H), 2. 80-2.90 (m, 2H), 2.65-2.80 (m, 1H), 2.23 (s, 3H).

Synthesis Example 11
Preparation of 3-methyl-5- {1- (pyridin-3-yl) -1H-pyrazol-4-yl} isoxazole (pyrazole derivative 14-001)
Process 1
Preparation of 3- [4-{(trimethylsilyl) ethynyl} -1H-pyrazol-1-yl] pyridine 1.0 g of 3- (4-iodo-1H-pyrazol-1-yl) pyridine 20 ml of N, N-dimethylformamide To the solution, 725 mg of trimethylsilylacetylene, 50 mg of copper iodide (monovalent), 50 mg of dichlorobistriphenylphosphine palladium (divalent) and 745 mg of triethylamine were sequentially added at room temperature. After completion of the addition, the reaction solution was stirred at 80 ° C. for 5 hours under nitrogen atmosphere. After completion of the reaction, 30 ml of water was added and extracted with ethyl acetate (50 ml × 1). The obtained organic layer was dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography eluting with n-hexane-ethyl acetate 4: 6 to obtain 0.4 g of the desired product as a pale yellow solid.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 8.97 (brs, 1H), 8.60 (d, J = 3.6 Hz, 1H), 8.09 (s, 1H), 8.04 ( d, J = 8.1 Hz, 1H), 7.84 (s, 1H), 7.43 (dd, J = 4.8, 8.1 Hz, 1H), 0.25 (s, 9H).

Process 2
Preparation of 3- (4-ethynyl-1H-pyrazol-1-yl) pyridine 3- [4-{(trimethylsilyl) ethynyl} -1H-pyrazol-1-yl] pyridine 1M tetrabutylammonium 2.9 ml of a fluoride tetrahydrofuran solution was added and stirred at room temperature for 15 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure, 20 ml of water was added, and the mixture was extracted with chloroform (20 ml × 1). The obtained organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography eluting with n-hexane-ethyl acetate 3: 7 to obtain 200 mg of the desired product as a white solid.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 8.97 (d, J = 2.4 Hz, 1H), 8.55-8.60 (m, 1H), 8.11 (s, 1H), 8.00-8.10 (m, 1H), 7.86 (s, 1H), 7.43 (dd, J = 4.8, 8.1 Hz, 1H), 3.13 (s, 1H).

Process 3
Preparation of 3-methyl-5- {1- (pyridin-3-yl) -1H-pyrazol-4-yl} isoxazole To a solution of acetoaldoxime 260 mg in dimethoxyethane 5 ml was added 590 mg N-chlorosuccinimide and 70 ° C. For 2 hours. After completion of the stirring, the reaction solution was cooled to room temperature, 250 mg of 3- (4-ethynyl-1H-pyrazol-1-yl) pyridine, 370 mg of potassium hydrogen carbonate and 0.5 ml of water were sequentially added, and the mixture was stirred at room temperature for 15 hours. Stirring was continued. After completion of the reaction, 20 ml of water was added and extracted with ethyl acetate (50 ml × 1). The obtained organic layer was dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography eluting with n-hexane-ethyl acetate 2: 8 to obtain 0.2 g of the objective product as a pale yellow solid.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 9.05 (d, J = 2.4 Hz, 1H), 8.62 (dd, J = 1.5, 4.8 Hz, 1H), 8.34 (S, 1H), 8.05-8.15 (m, 1H), 8.05 (s, 1H), 7.46 (dd, J = 4.5, 8.1 Hz, 1H), 6.24. (S, 1H), 2.36 (s, 3H).

Synthesis Example 12
Preparation of 4,4-dimethyl-2- [3-methyl-1- (pyridin-3-yl) -1H-pyrazol-4-yl] -4,5-dihydrooxazole (pyrazole derivative 15-001)
Process 1
Preparation of N- (1-hydroxy-2-methylpropan-2-yl) -3-methyl-1- (pyridin-3yl) -1H-pyrazole-4-carboxylic acid amide 3-Methyl-1- (pyridine- 3-yl) -1H-pyrazole-4-carboxylic acid To a suspension of 500 mg of hydrochloride in 10 ml of dichloromethane, 223 mg of 2-amino-2-methyl-1-propanol, 253 mg of triethylamine, 1-ethyl-3- (3-dimethyl) Aminopropyl) carbodiimide hydrochloride 480 mg and 4-dimethylaminopyridine 15 mg were sequentially added, and the mixture was stirred at room temperature for 24 hours. After completion of the reaction, 10 ml of water was added and extracted with 20 ml of ethyl acetate. The organic layer was separated, washed with saturated brine and then anhydrous sodium sulfate in this order and dried, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with a gradient of n-hexane-ethyl acetate (1: 1) to ethyl acetate-methanol (4: 1) to give 155 mg of the desired product as colorless. Obtained as an oil.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 8.95 (d, J = 3.0 Hz, 1H), 8.57 (d, J = 3.6 Hz, 1H), 8.27 (s, 1H ), 8.02 (dd, J = 9.9, 2.7 Hz, 1H), 7.41 (dd, J = 8.1, 4.8 Hz, 1H), 5.89 (brs, 1H), 5 .50 (brs, 1H), 3.58 (s, 2H), 2.55 (s, 3H), 1.29 (s, 6H).

Process 2
Preparation of N- (1-chloro-2-methylpropan-2-yl) -3-methyl-1- (pyridin-3-yl) -1H-pyrazole-4-carboxylic acid amide N- (1-hydroxy-2 To a solution of 130 mg of -methylpropan-2-yl) -3-methyl-1- (pyridin-3-yl) -1H-pyrazole-4-carboxylic acid amide in 3 ml of dichloromethane was added 68 mg of thionyl chloride, and 1 at room temperature. Stir for hours. After completion of the reaction, 5 ml of saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with 10 ml of ethyl acetate. The obtained organic layer was washed and dried in the order of saturated brine and then anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 145 mg of the desired product as a yellow oil.

Process 3
Preparation of 4,4-dimethyl-2- {3-methyl-1- (pyridin-3-yl) -1H-pyrazol-4-yl} -4,5-dihydrooxazole N- (1-chloro-2-methyl To a solution of 145 mg of propan-2-yl) -3-methyl-1- (pyridin-3-yl) -1H-pyrazole-4-carboxylic acid amide in 3 ml of ethanol was added 0.7 ml of 1M aqueous sodium hydroxide solution at room temperature. For 20 hours. After completion of the reaction, 5 ml of water was added and extracted with 10 ml of ethyl acetate. The obtained organic layer was washed and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with a gradient of n-hexane-ethyl acetate (1: 1) to ethyl acetate-methanol (4: 1) to give 35 mg of the objective compound as colorless. Obtained as an oil.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 8.95 (d, J = 2.7 Hz, 1H), 8.74 (dd, J = 1.2, 6.0 Hz, 1H), 8.33 (S, 1H), 8.02 (dd, J = 4.2, 8.1 Hz, 1H), 7.39 (dd, J = 4.2, 8.1 Hz, 1H), 4.04 (s, 2H), 2.56 (s, 3H), 1.37 (s, 6H).

Synthesis Example 13
Preparation of 3- [4- {1- (2,2,2-trifluoroethyl) -1H-1,2,4-triazol-3-yl} -1H-pyrazol-1-yl] pyridine (pyrazole derivative 12 -001)
Process 1
Preparation of N-{(dimethylamino) methylene} -1- (pyridin-3-yl) -1H-pyrazole-4-carboxamide 1.0 g of 1- (pyridin-3-yl) -1H-pyrazole-4-carboxamide To a 5 ml solution of N, N-dimethylformamide, 1.90 g of N, N-dimethylformamide dimethylacetal was added and stirred at 100 ° C. for 2 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. The obtained solid was washed with 5 ml of diisopropyl ether to obtain 0.89 g of the desired product as a pink solid.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 9.02 (d, J = 2.4 Hz, 1H), 8.64 (s, 1H), 8.57 (d, J = 4.5 Hz, 1H ), 8.52 (s, 1H), 8.24 (s, 1H), 8.11-8.02 (m, 1H), 7.48-7.37 (m, 1H), 3.20 ( s, 3H), 3.18 (s, 3H).

Process 2
Preparation of 3- {4- (1H-1,2,4-triazol-3-yl) -1H-pyrazol-1-yl} pyridine To a solution of hydrazine monohydrate 114 mg in acetic acid 5 ml, N-{(dimethylamino ) Methylene} -1- (pyridin-3-yl) -1H-pyrazole-4-carboxamide (0.89 g) was added, and the mixture was stirred at 90 ° C. for 2 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. The solid obtained after distilling off the solvent was washed with 5 ml of ethyl acetate to obtain 0.24 g of the desired product as a white solid.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 9.15 (d, J = 2.4 Hz, 1H), 9.02 (brs, 1H), 8.55-8.50 (m, 1H), 8.44-8.35 (m, 1H), 8.33-8.26 (m, 1H), 8.19 (brs, 1H), 7.54 (dd, J = 4.8, 8.4 Hz) , 1H), (the proton peak corresponding to NH was not detected).

Process 3
Preparation of 3- [4- {1- (2,2,2-trifluoroethyl) -1H-1,2,4-triazol-3-yl} -1H-pyrazol-1-yl] pyridine 60 wt% hydrogen 3- {4- (1H-1,2,4-triazol-3-yl) -1H-pyrazole-1 in a solution of 52 mg of sodium iodide (dispersed in mineral oil) in 5 ml of N, N-dimethylformamide at 0 ° C. After adding 0.24 g of -yl} pyridine, the mixture was stirred at room temperature for 30 minutes. After the stirring, 316 mg of 2,2,2-trifluoroethyl trifluoromethanesulfonic acid was added, and stirring was continued for 30 minutes at room temperature. After completion of the reaction, the reaction mixture was poured into ice water, and the precipitated solid was removed by filtration. The obtained solid was washed with 5 ml of a mixed solution of n-hexane: ethyl acetate [1: 1] to obtain 96 mg of the desired product as a white solid.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 9.05 (d, J = 2.4 Hz, 1H), 8.58 (dd, J = 1.2, 4.8 Hz, 1H), 8.51 (Brs, 1H), 8.26 (s, 1H), 8.20 (s, 1H), 8.10 (ddd, J = 1.2, 2.4, 8.4 Hz, 1H), 7.44 (Dd, J = 4.8, 8.4 Hz, 1H), 4.80 (q, J = 4.8 Hz, 2H).

Synthesis Example 14
3'-chloro-1- (methylthio) -1 '-(pyridin-3-yl) -1H, 1'H-3,4'-bipyrazole and 3'-chloro-2- (methylthio) -1'-( Preparation of pyridin-3-yl) -1′H, 2H-3,4′-bipyrazole (pyrazole derivative 1-060 and pyrazole derivative 2-006)
Process 1
Preparation of 3-chloro-N-methoxy-N-methyl-1- (pyridin-3-yl) -1H-pyrazole-4-amide 3-chloro-1- (pyridin-3-yl) -1H-pyrazole-4 -2.7 g of 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride, 1.1 g of N-methyl-N-methoxyamine and 4.1 g of triethylamine were sequentially added to a 20 ml solution of 2.0 g of carboxylic acid in dichloromethane. The mixture was added and stirred at room temperature for 15 hours. After completion of the reaction, 50 ml of water was added to the reaction mixture and extracted with 80 ml of ethyl acetate. The obtained organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. 10 ml of ethyl acetate was added to the residue obtained after distilling off the solvent, and the precipitated solid was removed by filtration. The solvent was distilled off from the obtained filtrate under reduced pressure to obtain 2.5 g of the objective product as a yellow oil.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 8.96 (d, J = 2.4 Hz, 1H), 8.63 (dd, J = 4.8, 1.5 Hz, 1H), 8.39 (S, 1H), 8.06 (ddd, J = 8.4, 2.7, 1.5 Hz, 1H), 7.50-7.40 (m, 1H), 3.70 (s, 3H) 3.37 (s, 3H).

Process 2
Preparation of 1- {3-chloro-1- (pyridin-3-yl) -1H-pyrazol-4-yl} ethanone 3-Chloro-N-methoxy-N-methyl-1- (pyridin-3-yl)- A solution of 2.5 g of 1H-pyrazole-4-amide in 20 ml of tetrahydrofuran was cooled to 0 ° C., 3.7 ml of 3 mol / L methylmagnesium bromide was added dropwise, and the mixture was stirred at room temperature for 15 hours. After completion of the stirring, 20 ml of 1N hydrochloric acid was added to stop the reaction. To the reaction solution, 20 ml of 2N aqueous sodium hydroxide solution was added, and extracted with 50 ml of ethyl acetate. The obtained organic layer was dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography eluting with n-hexane-ethyl acetate (1: 9) to obtain 1.1 g of the objective product as a white solid.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 8.99 (d, J = 2.7 Hz, 1H), 8.66 (dd, J = 4.8, 1.5 Hz, 1H), 8.46 (Brs, 1H), 8.05 (ddd, J = 8.4, 2.7, 1.5 Hz, 1H), 7.47 (ddd, J = 8.5, 4.8, 0.9 Hz, 1H) ), 2.61 (s, 3H).
Melting point: 82-83 ° C.

Process 3
Preparation of 1- {3-chloro-1- (pyridin-3-yl) -1H-pyrazol-4-yl) -3- (dimethylamino) -2-propen-1-one 1- {3-chloro-1 -(Pyridin-3-yl) -1H-pyrazol-4-yl} ethanone To a solution of 1.1 g of N, N-dimethylformamide dimethyl acetal in 5 ml was added 5 ml of t-butyl-bis (dimethylamino) methane at room temperature. For 3 days. After completion of the reaction, the solvent was distilled off under reduced pressure to obtain 1.2 g of the desired product as a white solid.

Process 4
Production of 3′-chloro-1 ′-(pyridin-3-yl) -1H, 1H′-3,4′-bipyrazole 1- {3-Chloro-1- (pyridin-3-yl) -1H-pyrazole- To a solution of 4-yl) -3- (dimethylamino) -2-propen-1-one (1.4 g) in ethanol (5 ml) was added hydrazine monohydrate (0.25 g), and the mixture was stirred at 90 ° C. for 2 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. 20 ml of n-hexane was added to the obtained residue, and the precipitated solid was collected by filtration to obtain 0.9 g of the desired product as a white solid.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 8.81 (d, J = 2.4 Hz, 1H), 8.40-8.30 (m, 1H), 7.90-7.80 (m , 1H), 7.41 (d, J = 2.1 Hz, 1H), 7.30-7.10 (m, 2H), 6.53 (d, J = 2.1 Hz, 1H), (to NH Corresponding proton peak was not detected).

Process 5
3'-chloro-1- (methylthio) -1 '-(pyridin-3-yl) -1H, 1'H-3,4'-bipyrazole and 3'-chloro-2- (methylthio) -1'-( Preparation of Pyridin-3-yl) -1′H, 2H-3,4′-bipyrazole 60 wt% sodium hydride (dispersed in mineral oil) 160 mg of N, N-dimethylformamide in 5 ml solution at 0 ° C. 800 mg of '-chloro-1'-(pyridin-3-yl) -1H, 1H'-3,4'-bipyrazole was added. After stirring at room temperature for 5 minutes, 410 mg of methylthiomethyl chloride was added, and stirring was continued for 15 hours at the same temperature. After completion of the reaction, the reaction mixture was poured into ice water and extracted with 50 ml of ethyl acetate. After drying over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography eluting with n-hexane-ethyl acetate (1: 9). 0.8 g of the desired product was obtained as a pale yellow solid [3′-chloro-1- (methylthio) -1 ′-(pyridin-3-yl) -1H, 1′H-3,4′-bipyrazole / 3 ′ -Chloro-2- (methylthio) -1 '-(pyridin-3-yl) -1'H, 2H-3,4'-bipyrazole = 1/1].
¹ H NMR of 3′-chloro-1- (methylthio) -1 ′-(pyridin-3-yl) -1H, 1′H-3,4′-bipyrazole (CDCl ₃ , Me ₄ Si, 300 MHz) δ9. 05-8.95 (m, 1H), 8.57 (dd, J = 4.8, 1.5 Hz, 1H), 8.36 (s, 1H), 8.10-8.00 (m, 1H) ), 7.66 (d, J = 2.4 Hz, 1H), 7.50-7.35 (m, 1H), 6.80 (d, J = 2.1 Hz, 1H), 5.17 (s) , 2H), 2.18 (s, 3H).
¹ H NMR of 3′-chloro-2- (methylthio) -1 ′-(pyridin-3-yl) -1′H, 2H-3,4′-bipyrazole (CDCl ₃ , Me ₄ Si, 300 MHz) δ9. 05-8.95 (m, 1H), 8.62 (dd, J = 4.8, 1.5 Hz, 1H), 8.32 (s, 1H), 8.10-8.00 (m, 1H) ), 7.59 (d, J = 2.1 Hz), 7.50-7.35 (m, 1H), 6.55 (d, J = 1.8 Hz, 1H), 5.19 (s, 2H) ), 2.26 (s, 3H).
Mp 95-100 ° C.

Synthesis Example 15
3′-chloro-1- (methylsulfinyl) -1 ′-(pyridin-3-yl) -1H, 1′H-3,4′-bipyrazole and 3′-chloro-2- (methylsulfinyl) -1 ′ Preparation of-(pyridin-3-yl) -1'H, 2H-3,4'-bipyrazole (pyrazole derivative 1-061 and pyrazole derivative 2-007)
3'-chloro-1- (methylthio) -1 '-(pyridin-3-yl) -1H, 1'H-3,4'-bipyrazole and 3'-chloro-2- (methylthio) -1'-( To a 5 ml acetic acid solution of 250 mg of a mixture of pyridin-3-yl) -1′H, 2H-3,4′-bipyrazole, 102 mg of 30 wt% aqueous hydrogen peroxide was added and stirred at room temperature for 4 hours. After completion of the reaction, 5 ml of a saturated aqueous sodium hydrogen sulfite solution was added, 30 ml of a saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was further extracted with 30 ml of ethyl acetate. The obtained organic layer was washed with water, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained solid was washed with 10 ml of ethyl acetate to obtain 100 mg of the desired product as a white solid [3′-chloro-1- (methylsulfinyl) -1 ′-(pyridin-3-yl) -1H, 1 ′. H-3,4'-bipyrazole / 3'-chloro-2- (methylsulfinyl) -1 '-(pyridin-3-yl) -1'H, 2H-3,4'-bipyrazole = 1/1].
Melting point: 154-160 ° C.

Synthesis Example 16
3'-chloro-1- (methylsulfonyl) -1 '-(pyridin-3-yl) -1H, 1'H-3,4'-bipyrazole and 3'-chloro-2- (methylsulfonyl) -1' Preparation of-(pyridin-3-yl) -1'H, 2H-3,4'-bipyrazole (pyrazole derivative 1-062 and pyrazole derivative 2-008)
3′-chloro-1- (methylsulfinyl) -1 ′-(pyridin-3-yl) -1H, 1′H-3,4′-bipyrazole and 3′-chloro-2- (methylsulfinyl) -1 ′ -(Pyridin-3-yl) -1'H, 2H-3,4'-bipyrazole mixture 200 mg of acetic acid in 5 ml solution, 163 mg of 30 wt% aqueous hydrogen peroxide and 10 mg of sodium tungstate dihydrate were sequentially added And stirred at room temperature for 4 hours. After completion of the reaction, 5 ml of a saturated aqueous sodium hydrogen sulfite solution was added, 30 ml of a saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was further extracted with 30 ml of ethyl acetate. The obtained organic layer was washed with water, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The solid obtained after distilling off the solvent was washed with 5 ml of a mixed solution of n-hexane: ethyl acetate (1: 1) to obtain 70 mg of the desired product as a white solid [3′-chloro-1- (methyl Sulfonyl) -1 ′-(pyridin-3-yl) -1H, 1′H-3,4′-bipyrazole / 3′-chloro-2- (methylsulfonyl) -1 ′-(pyridin-3-yl)- 1′H, 2H-3,4′-bipyrazole = 1/1].
Melting point: 165-170 ° C.

Synthesis Example 17
Preparation of 2-tert-butyl-5- (methylthiomethyl) -1 ′-(pyridin-3-yl) -1′H, 2H-3,4′-bipyrazole (pyrazole derivative 2-013)
Process 1
Preparation of 4- (4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl) -1-tosyl-1H-pyrazole 1H-pyrazole-4-boronic acid 450 mg dichloromethane 4 To the 0.6 ml solution, 22 mg of trimethylamine hydrochloride, 749 mg of N, N-diisopropylethylamine and 663 mg of p-toluenesulfonyl chloride were sequentially added and stirred at room temperature for 20 hours. After completion of the reaction, 6 ml of saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and the mixture was extracted with 15 ml of chloroform. The obtained organic layer was dehydrated and dried with saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (9: 1 to 1: 1 gradient) to obtain 567 mg of the desired product as a pale yellow solid.
Melting point: 140-141 ° C.

Process 2
Preparation of 2-tert-butyl-5- (methylthiomethyl) -1′-tosyl-1′H, 2H-3,4-bipyrazole 4- (4,4,5,5-tetramethyl-1,3,2 -Dioxaboran-2-yl) -1-tosyl-1H-pyrazole 540 mg and 1-tert-butyl-3- (methylthiomethyl) -1H-pyrazol-5-yl trifluoromethanesulfonate 620 mg of 1,4-dioxane To a solution of 3.9 ml and 1.3 ml of water, 115 mg of tripotassium phosphate and 126 mg of [1,1′-bis (diphenylphosphino) ferrocene] palladium (II) dichloride dichloromethane adduct were sequentially added. After completion of the addition, the inside of the reaction vessel was replaced with nitrogen gas, followed by stirring overnight at room temperature. After completion of the reaction, 4 ml of water was added to the reaction mixture and extracted with 12 ml of ethyl acetate. The obtained organic layer was dehydrated and dried with saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient 9: 1 to 1: 1) to obtain 510 mg of the objective product as a colorless oil.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 8.08 (s, 1H), 7.92 (d, J = 8.7 Hz, 2H), 7.69 (s, 1H), 7.36 ( d, J = 8.7 Hz, 2H), 6.10 (s, 1H), 3.64 (s, 2H), 2.45 (s, 3H), 2.10 (s, 3H), 1.45. (S, 9H).

Process 3
Preparation of 2-tert-butyl-5- (methylthiomethyl) -1′H, 2H-3,4′-bipyrazole To a mixed solution of 8.4 ml of methanol and 4.2 ml of tetrahydrofuran, 2-tert-butyl-5- ( Methylthiomethyl) -1′-tosyl-1 ′, 2H-3,4-bipyrazole (510 mg) and cesium carbonate (1.23 g) were sequentially added, and the mixture was stirred at room temperature for 2 hours. After completion of the reaction, 10 ml of water was added to the reaction mixture and extracted with 30 ml of ethyl acetate. The obtained organic layer was dehydrated and dried with saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient of 9: 1 to 3: 1) to obtain 96.2 mg of the desired product as a white solid. .
Melting point: 119-120 ° C.

Process 4
Preparation of 2-tert-butyl-5- (methylthiomethyl) -1 ′-(pyridin-3-yl) -1′H, 2H-3,4′-bipyrazole 2-tert-butyl-5- (methylthiomethyl) -1'H, 2H-3,4'-bipyrazole in a solution of 82 mg of N, N-dimethylformamide 0.3 ml, 67 mg of 3-bromopyridine, 19 mg of copper iodide (monovalent), 290 mg of cesium carbonate and trans-N , N′-dimethylcyclohexane-1,2-diamine (27 mg) was sequentially added. After completion of the addition, the inside of the reaction vessel was replaced with nitrogen gas, followed by stirring at 140 ° C. for 2 hours. After completion of the reaction, 5 ml of water was added to the reaction mixture and extracted with 15 ml of ethyl acetate. The obtained organic layer was dehydrated and dried with saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient of 9: 1 to 3: 2) to obtain 101 mg of the objective product as a white solid.
Melting point: 77-78 ° C.

Synthesis Example 18
Preparation of 2-{(methylthio) methyl} -7- (pyridin-3-yl) -5,7-dihydro-2H-thiopyrano [3,2-c: 5,4-c ′] dipyrazole (pyrazole derivative 7- 007)
Process 1
Preparation of 5,7-dihydrothiopyrano [3,4-c] pyrazol-4 (2H) -one Journal Heterocyclic Chemistry 1984, Vol. 21, p. 1437 ) 6.73 g of hydrazine monohydrate was added to a solution of 24.8 g of methylene} -2H-thiopyran-3,5- (4H, 6H) -dione in 400 ml of methanol and stirred at room temperature for 1 hour. After completion of the reaction, the solvent was distilled off from the reaction mixture under reduced pressure. The obtained residue was purified by silica gel chromatography eluting with ethyl acetate to obtain 10 g of the desired product as a yellow solid.
¹ H NMR (CDCl ₃ , Me ₄ Si, 400 MHz) δ 7.95 (s, 1H), 3.79 (s, 2H), 3.33 (s, 2H) (no NH peak was observed)
Process 2
2- (1-Ethoxyethyl) -5,7-dihydrothiopyrano [3,4-c] pyrazol-4 (2H) -one and 1- (1-ethoxyethyl) -5,7-dihydrothiopyrano Preparation of [3,4-c] pyrazol-4 (1H) -one To a solution of 8.9 g of 5,7-dihydrothiopyrano [3,4-c] pyrazol-4 (2H) -one in 100 ml of tetrahydrofuran was added ethyl acetate. 25.0 g of vinyl ether and 0.2 ml of concentrated hydrochloric acid were sequentially added, and the mixture was stirred for 16 hours under reflux of tetrahydrofuran. After completion of the reaction, the solvent was distilled off from the reaction mixture under reduced pressure. The obtained residue was purified by silica gel chromatography eluting with ethyl acetate to obtain 12 g of the desired product as a yellow oil.
¹ H NMR (CDCl ₃ , Me ₄ Si, 400 MHz) δ 8.04-7.88 (m, 1H), 5.63-5.40 (m, 1H), 4.09-3.80 (m, 2H ), 3.50-3.30 (m, 4H), 1.68-1.41 (m, 3H), 1.22-1.14 (m, 3H).

Process 3
5-{(dimethylamino) methylene} -2- (1-ethoxyethyl) -5,7-dihydrothiopyrano [3,4-c] pyrazol-4 (2H) -one and 5-{(dimethylamino) Preparation of methylene} -1- (1-ethoxyethyl) -5,7-dihydrothiopyrano [3,4-c] pyrazol-4 (1H) -one 2- (1-ethoxyethyl) -5,7- Dihydrothiopyrano [3,4-c] pyrazol-4 (2H) -one and 1- (1-ethoxyethyl) -5,7-dihydrothiopyrano [3,4-c] pyrazole-4 (1H) 120 ml of N, N-dimethylformamide dimethyl acetal was added to 12 g of the mixture of -one, and the mixture was stirred for 3 hours under reflux of N, N-dimethylformamide dimethyl acetal. After completion of the reaction, N, N-dimethylformamide dimethyl acetal was distilled off from the reaction mixture under reduced pressure. The obtained residue was purified by silica gel chromatography eluting with ethyl acetate to obtain 14 g of the desired product as a yellow oil.
¹ H NMR (CDCl ₃ , Me ₄ Si, 400 MHz) δ 7.96-7.70 (m, 2H), 5.53-5.33 (m, 1H), 4.05-3.70 (m, 2H) ), 3.39-3.35 (m, 2H), 3.18-3.16 (m, 6H), 1.60-1.58 (m, 3H), 1.11-1.08 (m) , 3H).

Process 4
7- (1-Ethoxyethyl) -5,7-dihydro-2H-thiopyrano [3,2-c: 5,4-c ′] dipyrazole and 6- (1-Ethoxyethyl) -5,6-dihydro-2H -Preparation of thiopyrano [3,2-c: 5,4-c '] dipyrazole 5-{(dimethylamino) methylene} -2- (1-ethoxyethyl) -5,7-dihydrothiopyrano [3,4 -C] pyrazol-4 (2H) -one and 5-{(dimethylamino) methylene} -1- (1-ethoxyethyl) -5,7-dihydrothiopyrano [3,4-c] pyrazole-4 ( To a solution of 14 g of 1H) -one in 150 ml of methanol, 5 g of hydrazine monohydrate was added and stirred for 2 hours under reflux of methanol. After completion of the reaction, the solvent was distilled off from the reaction mixture under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (3: 1 to 1: 1 gradient) to obtain 11 g of the objective product as a yellow oil.
¹ H NMR (CDCl ₃ , Me ₄ Si, 400 MHz) δ 7.87-7.78 (m, 1H), 7.46-7.44 (m, 1H), 5.69-5.47 (m, 1H ), 4.27-4.06 (m, 2H), 3.51-3.39 (m, 2H), 1.72-1.69 (m, 3H), 1.20-1.17 (m) , 3H), (the proton peak corresponding to NH was not detected).

Process 5
7- (1-ethoxyethyl) -2-{(methylthio) methyl} -5,7-dihydro-2H-thiopyrano [3,2-c: 5,4-c ′] dipyrazole, 7- (1-ethoxyethyl) ) -1-{(methylthio) methyl} -5,7-dihydro-1H-thiopyrano [3,2-c: 5,4-c ′] dipyrazole, 6- (1-ethoxyethyl) -2-{(methylthio ) Methyl} -5,6-dihydro-2H-thiopyrano [3,2-c: 5,4-c ′] dipyrazole and 6- (1-ethoxyethyl) -1-{(methylthio) methyl} -5,6 Preparation of dihydro-1H-thiopyrano [3,2-c: 5,4-c ′] dipyrazole 7- (1-Ethoxyethyl) -5,7-dihydro-2H-thiopyrano [3,2-c: 5 4-c ′] dipyrazole and 6- (1-ethoxyethyl) A mixture of 6.8 g of 5,6-dihydro-2H-thiopyrano [3,2-c: 5,4-c ′] dipyrazole in 100 ml of tetrahydrofuran was added at 0 ° C. with 60 wt% sodium hydride (in mineral oil). Dispersion) 1.2 g was added and stirred for 30 minutes. After completion of stirring, 2.87 g of chloromethyl methyl sulfide was added to the reaction mixture, and stirring was continued at room temperature for 2 hours. After completion of the reaction, 100 ml of saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with 400 ml of ethyl acetate. The obtained organic layer was dehydrated and dried with saturated brine and then anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 13 g of the objective product as a yellow oil.

Step 6
2-{(methylthio) methyl} -5,7-dihydro-2H-thiopyrano [3,2-c: 5,4-c ′] dipyrazole and 1-{(methylthio) methyl} -5,7-dihydro-1H -Preparation of thiopyrano [3,2-c: 5,4-c '] dipyrazole 7- (1-ethoxyethyl) -2-{(methylthio) methyl} -5,7-dihydro-2H obtained in step 5 -Thiopyrano [3,2-c: 5,4-c '] dipyrazole, 7- (1-ethoxyethyl) -1-{(methylthio) methyl} -5,7-dihydro-1H-thiopyrano [3,2- c: 5,4-c ′] dipyrazole, 6- (1-ethoxyethyl) -2-{(methylthio) methyl} -5,6-dihydro-2H-thiopyrano [3,2-c: 5,4-c '] Dipyrazole and 6- (1-ethoxyethyl) -1- { To 13 g of a mixture of (methylthio) methyl} -5,6-dihydro-1H-thiopyrano [3,2-c: 5,4-c ′] dipyrazole was added 100 ml of an ethyl acetate solution of about 4M hydrogen chloride at room temperature. Stir for 16 hours. After completion of the reaction, the solvent was distilled off from the reaction mixture under reduced pressure. 100 ml of water was added to the resulting residue, and further sodium bicarbonate was added to adjust the pH of the reaction mixture to 7, followed by extraction with 400 ml of a mixed solution of ethyl acetate: tetrahydrofuran (2: 1). The obtained organic layer was dehydrated and dried with saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by medium pressure preparative liquid chromatography eluting with dichloromethane-tetrahydrofuran (100: 1 to 5: 1 gradient) to give 2-{(methylthio) methyl} -5,7-dihydro. 1.1 g of -2H-thiopyrano [3,2-c: 5,4-c '] dipyrazole as a yellow solid and 1-{(methylthio) methyl} -5,7-dihydro-1H-thiopyrano [3,2- c: 5,4-c ′] dipyrazole 1.1 g was obtained as a yellow solid.
¹ H NMR (CDCl ₃ , Me ₄ Si, 400 MHz) δ 7.86 of 2-{(methylthio) methyl} -5,7-dihydro-2H-thiopyrano [3,2-c: 5,4-c ′] dipyrazole (S, 1H), 7.44 (s, 1H), 5.10 (s, 2H), 4.02 (s, 2H), 2.16 (s, 3H), (NH peaks are not observed. ),
1 - {(methylthio) methyl} -5,7-dihydro -1H- thiopyrano [3,2-c: 5,4-c '] Jipirazoru of _{^{1 H NMR (CDCl 3, Me}} 4 Si, 400MHz) δ7.80 (S, 1H), 7.38 (s, 1H), 5.23 (s, 2H), 3.99 (s, 2H), 2.18 (s, 3H), (NH peaks are not observed. .)

Step 7
Preparation of 2-{(methylthio) methyl} -7- (pyridin-3-yl) -5,7-dihydro-2H-thiopyrano [3,2-c: 5,4-c ′] dipyrazole 2-{(methylthio ) Methyl} -5,7-dihydro-2H-thiopyrano [3,2-c: 5,4-c ′] dipyrazole 500 mg in 1-methyl-2-pyrrolidone 10 ml solution, 3-iodopyridine 516 mg, copper iodide (Monovalent) 160 mg, trans-N, N′-dimethylcyclohexane-1,2-diamine hydrochloride 451 mg and cesium carbonate 1.71 g were sequentially added. After completion of the addition, the inside of the reaction vessel was replaced with argon gas, followed by stirring at 160 ° C. for 30 minutes. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, and the reaction mixture was added to 100 ml of water and extracted with 600 ml of ethyl acetate. The obtained organic layer was dehydrated and dried over saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was recrystallized with a mixed solvent of methanol / tetrahydrofuran / dichloromethane (0.5 ml / 2 ml / 20 ml), and the obtained solid was washed with 6 ml of ethyl acetate to obtain 300 mg of the desired product as a white solid. .
¹ H NMR (CDCl ₃ , Me ₄ Si, 400 MHz) δ 9.01 (d, J = 2.4 Hz, 1H), 8.57 (d, J = 4.8 Hz, 1H), 8.26 (d, J = 8.4 Hz, 1H), 8.05 (d, J = 8.4 Hz, 1H), 7.50 (s, 1H), 7.44 (dd, J = 8.4, 4.8 Hz, 1H) 5.15 (s, 2H), 4.09 (s, 2H), 2.21 (s, 3H).

The pyrazole derivative represented by the general formula (1), which is an active ingredient of the parasite control agent of the present invention, can be produced according to the production method and the examples. Examples of pyrazole derivatives produced in the same manner as in Synthesis Examples 1 to 18 are shown in Tables 11 to 30 and their physical property values are shown in Tables 31 and 32. The effectiveness of the parasite control agent of the present invention is shown in FIG. The pyrazole derivative represented by the general formula (1) as a component is not limited to these. In the table, D2-7a, D2-32a, D2-32b, D2-33a, D2-34a, D2-34b, D2-37a, D2-37b, D2-81a, D2-82a, D2-108a, D2 structure represented by -108b represents the following structures, D2-32b, D2-34b, numbers written in the structural formula of D2-37b represents the substitution position of ^{X 2,} the structural formula of D2-108b marked number represents a substituted position of Z ^2. * 1 represents resinous form.

The symbols in Table 31 and Table 32 represent the following meanings.
s: singlet, d: doublet, t: triplet, q: quartet, qui: quintet, m: multiplet, brs: broad peak.

  Table 11

[Table 11]
――――――――――――――――――――――――――――――――――
No. R ³ R ⁴ X ¹ X ^1a mp (℃)
――――――――――――――――――――――――――――――――――
1-001 Me HH CH ₂ CF ₃ 152-153
1-002 Me HH D2-37a 217-218
1-003 Me HHH 167-168
1-004 Me HHC (O) NHCH ₂ CF ₃ 164-165
1-005 Me HH D2-32a 176-178
1-006 Me HH D2-37b (4,6-bisCF ₃ ) 209-210
1-007 Me HH CH ₂ SCH ₃ 107-108
1-008 Me HH CH ₂ S (O) ₂ CH ₃ 153-155
1-009 HHHH 168-170
1-010 HHH CH ₂ CF ₃ 170-173
1-011 Me HHC (O) CH ₃ 190-198
1-012 Me HHC (O) N (Me) CH ₂ CH ₃ 142-144
1-013 Me HHC (O) OCH ₂ CH ₃ 150-151
1-014 HHH D2-37a 250-255
1-015 Me HH D2-108b (2-CF ₃ ) 82-84
1-016 Me HH D2-32b (3-Cl) 160-162
1-017 Me HH D2-33a 190-192
1-018 Me HH D2-34a 184-186
1-019 Me HH D2-34b (2-Cl) 201-205
1-020 Me HH CH ₂ (D2-32a) 119-122
1-021 Me HH CH ₂ S (O) (= NCN) CH ₃ 124-128
1-022 Me HH CH ₂ CN 156-159
1-023 Me HH D2-32b (6-Cl) 203-206
1-024 Me HH D2-32b (5-Cl) 244-246
1-025 Me HH CH ₂ S (= NCN) CH ₃ 179-183
1-026 Me HH CH ₂ CH ₃ 82-84
1-028 Me HHS (O) ₂ CH ₃ 142-144
1-029 Me HHS (O) ₂ {D2-108b (4-Me)} 149-152
1-031 Me HHC (O) SCH ₃ 202-205
1-032 Me HH CH ₂ (D2-108a) 126-128
1-033 Me HH CH ₂ SC (O) CH ₃ 118-122
1-034 Me HH CH ₂ OCH ₃ 92-94
――――――――――――――――――――――――――――――――――
[Table 11] (continued)
――――――――――――――――――――――――――――――――――
No. R ³ R ⁴ X ¹ X ^1a mp (℃)
――――――――――――――――――――――――――――――――――
1-035 Me HHC (S) NHCH ₂ CH ₃ 178-180
1-036 Me HH CH ₂ (D2-7a) 156-160
1-037 Me HHC (O) NHCH ₂ CH ₃ * 1
1-038 Me HH CH ₂ CH (OCH ₂ CH ₃ ) ₂ 87-90
1-039 Me HH CH ₂ CHF ₂ 105-107
1-040 Me HH SO ₂ N (CH ₃ ) ₂ 116-118
1-041 Me HHC (O) NHC (O) OCH ₃ 177-179
1-042 Me HH CH ₂ CH ₂ CH ₃ 84-85
1-043 Me HH CH (CH ₃ ) ₂ 95-96
1-045 Me H OMe CH ₂ CF ₃ 146-147
1-046 Me HH CH ₂ SCH ₂ CF ₃ 128-131
1-048 Me HH CH ₂ SCH ₂ CH ₃ 87-88
1-049 Me HH CH ₂ C (O) NHCH ₃ 186-190
1-050 Me HH CH ₂ OCH ₂ CF ₃ 144-145
1-052 Me HH CH ₂ C≡CH 134-136
1-053 Me H SCH ₃ H 141-142
1-054 HHH CH ₂ SCH ₃ 81-86
1-055 Me H OH CH ₂ CF ₃ 190-191
1-058 Me H SMe CH ₂ CF ₃ 154-155
1-059 Cl HH CH ₂ CF ₃ 161-162
1-060 Cl HH CH ₂ SCH ₃ 95-100 (* 2)
1-061 Cl HH CH ₂ S (O) CH ₃ 154-160 (* 3)
1-062 Cl HH CH ₂ S (O) ₂ CH ₃ 165-170 (* 4)
1-063 HH CH ₂ SCH ₃ Me 64-65 (* 5)
1-064 HH CH ₂ S (O) CH ₃ Me 245-246 (* 6)
1-065 HH CH ₂ S (O) ₂ CH ₃ Me 156-157 (* 7)
1-066 HH CH ₂ SCH ₃ CH ₂ CF ₃ 73-74 (* 8)
1-067 Me HH CH (CH ₃ ) SCH ₂ CH ₃ * 1
――――――――――――――――――――――――――――――――――
* 2 is a mixture of pyrazole derivative 1-060 and pyrazole derivative 2-006, which are isomers having different structures, as described in Synthesis Example 14, and the ratio is 1-060 / 2-006 = 1/1 .
* 3 is a mixture of pyrazole derivative 1-061 and pyrazole derivative 2-007, which are isomers having different structures, as described in Synthesis Example 15, and the ratio is 1-061 / 2-007 = 1/1 .
* 4 is a mixture of pyrazole derivative 1-062 and pyrazole derivative 2-008, which are isomers having different structures, as described in Synthesis Example 16, and the ratio is 1-062 / 2-2008 = 1/1 .
* 5 is a mixture of pyrazole derivative 1-063 and pyrazole derivative 2-009 which are isomers having different structures, and the ratio thereof is 1-063 / 2-009 = 3/1.
* 6 is a mixture of pyrazole derivative 1-064 and pyrazole derivative 2-010 which are isomers having different structures, and the ratio thereof is 1-064 / 2-010 = 7/3.
* 7 is a mixture of pyrazole derivative 1-065 and pyrazole derivative 2-011, which are isomers having different structures, and the ratio is 1-065 / 2-011 = 3/1.
* 8 is a mixture of pyrazole derivative 1-066 and pyrazole derivative 2-012, which are isomers having different structures, and the ratio thereof is 1-066 / 2-012 = 3/1.

  Table 12

[Table 12]
――――――――――――――――――――――――――――――――――
No. R ³ R ⁴ X ¹ X ^1a mp (℃)
――――――――――――――――――――――――――――――――――
2-002 Me H OCH ₂ CF ₃ CH ₃ 94-96
2-003 Me H OCH ₂ CF ₃ H 181-183
2-004 Me H OH H 260 (decomp.)
2-005 HHH CH ₂ SCH ₃ 85-95
2-012 HH CH ₂ SCH ₃ CH ₂ CF ₃ 73-74 (* 8)
2-013 HH CH ₂ SCH ₃ Bu-t 77-78
――――――――――――――――――――――――――――――――――
Table 13

[Table 13]
――――――――――――――――――――――――――――――――――
No. R ³ R ⁴ X ¹ X ^1a mp (℃)
――――――――――――――――――――――――――――――――――
3-001 HHH CH ₂ CF ₃ 157-159
3-002 HHH D2-37a 270 (decomp.)
――――――――――――――――――――――――――――――――――
Table 14

[Table 14]
――――――――――――――――――――――――――――――
No. R ³ R ⁴ X ¹ mp (℃)
――――――――――――――――――――――――――――――
4-001 Me H CF ₂ CF ₃ 97-102
4-002 HH CF ₂ CF ₃ 97-100
4-003 HHC (O) OCH ₂ CH ₃ 129-132
4-004 HHC (O) NHCH ₂ CF ₃ 168-173
4-005 HHH 116-118
4-006 HH D2-32a 198-200
4-007 HH SCH ₃ 124-125
4-008 HHS (O) CH ₃ 150-152
4-009 HHS (O) ₂ CH ₃ 175-178
4-010 HH CH ₂ SCH ₃ 104-106
4-011 HH SCH ₂ CH ₃ 59-60
4-012 HH CH ₂ OH 135-137
4-013 HH CH ₂ Cl 247-250
4-014 HH CH ₂ S (O) CH ₃ 141-142
4-015 HH CH ₂ S (O) ₂ CH ₃ 164-166
4-016 HH CH ₂ SCH ₂ CF ₃ 89-91
4-017 HHS (O) CH ₂ CH ₃ 111-112
4-018 Cl H CH ₂ SCH ₃ 92-93
4-019 Cl H CH ₂ S (O) ₂ CH ₃ 144-146
4-020 Cl H CH ₂ S (O) CH ₃ 120-122
4-022 Me H CH ₂ S (O) ₂ CH ₃ 121-122
―――――――――――――――――――――――――――――――
Table 15

[Table 15]
―――――――――――――――――――――――――――――
No. R ³ R ⁴ X ¹ mp (℃)
―――――――――――――――――――――――――――――
5-001 HHC (O) OCH ₂ CH ₃ 73-76
5-002 HHC (O) NHCH ₂ CF ₃ 152-156
5-003 HHI 200-203
―――――――――――――――――――――――――――――
Table 16

[Table 16]
――――――――――――――――――――――――――――
No. R ³ R ⁴ Z ¹ mp (℃)
――――――――――――――――――――――――――――
6-001 HH 4-CF ₃ 141-144
6-002 HH 3-CF ₃ 150-156
6-003 HH 2-CF ₃ 52-53
6-004 HH 4-SCH ₃ 125-127
6-005 HH 4-OCF ₃ 122-128
6-006 HH 4-OCH ₃ 113-115
6-007 HH 4-C (O) NHCH ₂ CF ₃ 220 (decomp.)
6-008 HH 4-CH = NOCH ₃ 152-154
6-009 HH 4-S (O) ₂ CH ₃ 189-192
6-010 HH 4-CH ₃ 133-134
6-011 HH 4-Cl 145-147
6-012 HH 4-C (O) CH ₃ 136-139
6-013 HH 4-SCF ₃ 180-184
―――――――――――――――――――――――――――――
Table 17

[Table 17]
――――――――――――――――――――――――――
No. R ⁴ A ³ X ^1a mp (℃)
――――――――――――――――――――――――――
7-001 H CH ₂ CF ₂ CF ₃ 216-218
7-002 H CH ₂ CH ₂ SCH ₃ 146-149
7-003 H CH ₂ CH ₂ OCH ₃ 132-136
7-004 H CH ₂ CH ₂ CN 163-167
7-007 HS CH ₂ SCH ₃ 175-177
7-008 H CH ₂ CH ₂ S (O) CH ₃ 190-195
7-009 H CH ₂ CH ₂ S (O) ₂ CH ₃ 246-247
7-010 HC (CH ₃ ) ₂ CH ₂ S (O) CH ₃ * 1
7-011 HC (CH ₃ ) ₂ CH ₂ S (O) ₂ CH ₃ * 1
―――――――――――――――――――――――――――
Table 18

[Table 18]
――――――――――――――――――――――――――
No. R ⁴ A ³ X ^1a mp (℃)
――――――――――――――――――――――――――
8-001 H CH ₂ CF ₂ CF ₃ 123-132
8-002 H CH ₂ CH ₂ SCH ₃ 145-146
8-003 H CH ₂ CH ₂ OCH ₃ 125-126
――――――――――――――――――――――――――
Table 19

[Table 19]
――――――――――――――――――――――――――――――――
No. R ³ R ⁴ X ^1-1 X ^1-2 mp (℃)
――――――――――――――――――――――――――――――――
9-001 HH CF ₃ H 163-164
9-002 HH SCH ₃ H 127-128
9-003 HHH SCH ₃ 93-95
――――――――――――――――――――――――――――――――
Table 20

[Table 20]
――――――――――――――――――――――
No. R ³ R ⁴ X ¹ mp (℃)
――――――――――――――――――――――
10-001 HHH 155-156
――――――――――――――――――――――
Table 21

[Table 21]
――――――――――――――――――――――
No. R ³ R ⁴ X ¹ mp (℃)
――――――――――――――――――――――
11-001 HHH 142-145
――――――――――――――――――――――
Table 22

[Table 22]
―――――――――――――――――――――――――――
No. R ³ R ⁴ X ¹ X ^1a mp (℃)
―――――――――――――――――――――――――――
12-001 HHH CH ₂ CF ₃ 187-189
―――――――――――――――――――――――――――
Table 23

[Table 23]
――――――――――――――――――――
No. R ³ R ⁴ X ¹ mp (℃)
――――――――――――――――――――
13-001 HHH 95-97
――――――――――――――――――――
Table 24

[Table 24]
――――――――――――――――――――――
No. R ³ R ⁴ X ¹ mp (℃)
――――――――――――――――――――――
14-001 HH Me 103-105
――――――――――――――――――――――
Table 25

[Table 25]
―――――――――――――――――――――――――
No. R ³ R ⁴ X ^1-1 X ^1-2 mp (℃)
―――――――――――――――――――――――――
15-001 Me H Me Me * 1
―――――――――――――――――――――――――
Table 26

[Table 26]
――――――――――――――――――――――――――――
No. R ⁴ A ³ X ¹ mp (℃)
――――――――――――――――――――――――――――
16-001 H CH ₂ D2-37a 216-219
16-002 H CH ₂ CH ₂ SCH ₃ 128-132
16-003 HC (CH ₃ ) ₂ CH ₂ SCH ₃ 151-154
16-007 H CH ₂ CH ₂ S (O) CH ₃ 122-124
16-009 HC (CH ₃ ) ₂ CH ₂ S (O) CH ₃ 165-169
16-011 H CH (CH ₃ ) CH ₂ S (O) CH ₃ 200-202
――――――――――――――――――――――――――――
Table 27

[Table 27]
―――――――――――――――――――――――――
No. R ³ R ⁴ X ¹ X ^1a mp (℃)
―――――――――――――――――――――――――
17-001 Me HH CH ₂ CF ₃ 200-206
―――――――――――――――――――――――――
Table 28

[Table 28]
―――――――――――――――――――――――――
No. R ³ R ⁴ X ^1-1 X ^1-2 mp (℃)
―――――――――――――――――――――――――
18-001 HH CH ₂ SCH ₃ H 94-96
―――――――――――――――――――――――――
Table 29

[Table 29]
―――――――――――――――――――――
No. R ³ R ⁴ X ¹ mp (℃)
―――――――――――――――――――――
21-001 Me H SCH ₃ 113-114
―――――――――――――――――――――
Table 30

[Table 30]
――――――――――――――――――――――――
No. R ³ R ⁴ X ¹ mp (℃)
――――――――――――――――――――――――
22-001 Me H CH ₂ SCH ₃ 126-128
――――――――――――――――――――――――
[Table 31]
――――――――――――――――――――――――――――――――――
No.
Proton nuclear magnetic resonance chemical shift value (in CDCl ₃ ): σ (ppm)
――――――――――――――――――――――――――――――――――
1-037;
8.99 (d, J = 2.7 Hz, 1H), 8.53 (d, J = 4.8 Hz, 1H), 8.26 (d, J = 1.8 Hz, 1H), 8.24 (s , 1H), 8.00-8.10 (m, 1H), 7.39 (dd, J = 4.8, 8.4 Hz, 1H), 7.16 (brs, 1H), 6.54 (s) , 1H), 3.53 (qui, J = 7.2 Hz, 2H), 2.59 (s, 3H), 1.31 (t, J = 7.2 Hz, 3H)
2-001;
9.00 (d, J = 3.3 Hz, 1H), 8.57 (d, J = 4.8 Hz, 1H), 8.21 (s, 1H), 8.00-8.10 (m, 1H) ), 7.58 (d, J = 1.8 Hz, 1H), 7.43 (dd, J = 4.8, 8.4 Hz, 1H), 6.37 (d, J = 1.8 Hz, 1H) 5.14 (s, 2H), 2.36 (s, 3H), 2.29 (s, 3H)
15-001;
8.95 (d, J = 2.7 Hz, 1H), 8.74 (dd, J = 1.2, 6.0 Hz, 1H), 8.33 (s, 1H), 8.02 (dd, 4 .2, 8.1 Hz, 1H), 7.39 (dd, 4.2, 8.1 Hz, 1H), 4.04 (s, 2H), 2.56 (s, 3H), 1.37 (s) , 6H)
1-067;
8.98 (d, J = 2.7 Hz, 1H), 8.49 (dd, J = 4.8, 1.5 Hz, 1H), 8.19 (s, 1H), 8.10-8.00 (M, 1H), 7.72 (d, J = 2.7 Hz, 1H), 7.37 (dd, J = 8.4, 4.8 Hz, 1H), 6.46 (d, J = 2. 7 Hz, 1H), 5.56 (q, J = 6.9 Hz, 1H), 2.55 (s, 3H), 2.35-2.50 (m, 2H), 1.80 (d, J = 6.9 Hz, 3H), 1.19 (t, J = 7.5 Hz, 3H)
1-068;
9.00 (brs, 1H), 8.55-8.50 (m, 1H), 8.22 (s, 1H), 8.10-8.00 (m, 1H), 7.80-7. 70 (m, 1H), 7.45-7.30 (m, 1H), 6.45-6.40 (m, 1H), 5.44 (q, J = 6.9 Hz, 1H), 2. 59 (s, 3H), 2.05 (s, 3H), 1.83 (d, J = 6.9 Hz, 3H)
7-010;
9.05-8.95 (m, 1H), 8.55-8.45 (m, 1H), 8.20 (s, 1H), 8.10-8.00 (m, 1H), 7. 48 (s, 1H), 7.43 (dd, J = 8.4, 4.8 Hz, 1H), 5.33 (d, J = 13.5 Hz, 1H), 5.20 (d, J = 13) .5Hz, 1H), 2.83 (s, 2H), 2.57 (s, 3H), 2.10 (s, 6H)
――――――――――――――――――――――――――――――――――
[Table 32]
――――――――――――――――――――――――――――――――――
No.
Proton nuclear magnetic resonance chemical shift value (in DMSO-d6): σ (ppm)
――――――――――――――――――――――――――――――――――
7-011;
9.05-8.95 (m, 1H), 8.55-8.45 (m, 1H), 8.21 (s, 1H), 8.10-8.00 (m, 1H), 7. 50 (s, 1H), 7.43 (dd, J = 8.4, 4.8 Hz, 1H), 5.33 (s, 2H), 2.95 (s, 3H), 2.84 (s, 2H), 2.02 (s, 6H)
――――――――――――――――――――――――――――――――――
The proton nuclear magnetic resonance chemical shift values in Tables 31 and 32 were measured at 300 MHz using Me4Si (tetramethylsilane) as a reference material.
[Test example]
Next, the usefulness of the parasite control agent of the present invention will be specifically described in the following test examples, but the present invention is not limited thereto.

Test Example 1 Effect test on cat fleas 3.5 mg of pyrazole derivative was dissolved in 3.5 ml of acetone to prepare a chemical solution having a concentration of 1000 ppm. After 350 μl of this chemical solution was applied to the bottom and side surfaces of a glass container having an inner wall surface area of 35 cm ² , acetone was volatilized to form a thin film of pyrazole derivative on the inner wall of the glass container. Since the inner wall of the used glass container is 35 cm ² , the treatment dose is 10 μg / cm ² . Five cat fleas (Ctenocephalides felis) adults (mixed males and females) were released on this, covered, and housed in a thermostatic chamber at 25 ° C. After 4 days, the number of insects with behavioral abnormalities was investigated, and the efficiency (%) was calculated from the following formula. In addition, the test was performed by 2 continuous systems.

efficacy (%) = (number of insects with behavioral abnormalities derived from compounds / number of worms) × 100
As a result, among the compounds tested, the following compounds showed an efficiency (%) of 80% or more.
Pyrazole derivative compound no. : 1-046, 1-048, 1-050, 1-052, 1-054, 1-058 to 1-067, 2-002 to 2-004, 2-013, 4-003, 4-006, 4 -007, 4-010, 4-012-4-014, 4-016 to 4-020, 6-013, 7-001 to 7-004, 7-008, 8-002, 8-003, 9-002 , 9-003, 16-001, 18-001, 22-001
Test Example 2 Effect test on tick (American dog tick) 3.5 mg of pyrazole derivative was dissolved in 3.5 ml of acetone to prepare a chemical solution having a concentration of 1000 ppm. After 350 μl of this chemical solution was applied to the bottom and side surfaces of a glass container having an inner wall surface area of 35 cm ² , acetone was volatilized to form a thin film of pyrazole derivative on the inner wall of the glass container. Since the inner wall of the used glass container is 35 cm ² , the treatment dose is 10 μg / cm ² .

  Five American dog tick (Dermacentor variabilis) first nymphs (mixed males and females) were released, covered, and housed in a thermostatic chamber at 25 ° C. The number of insects in which behavioral abnormalities were observed after 4 days was investigated, and the efficiency (%) was calculated from the same calculation formula as in Test Example 1. In addition, the test was performed by 2 continuous systems.

As a result, among the compounds tested, the following compounds showed an efficiency (%) of 80% or more.
Pyrazole derivative compound no. : 1-048, 1-052, 1-054, 1-058 to 1-060, 1-067, 2-002, 2-013, 6-013, 7-004, 9-002, 9-003, 16 -001,

  The parasite control agent of the present invention is an existing parasite control agent such as an organophosphorus compound, a carbamate compound or a pyrethroid compound that is parasitic on mammals, birds, etc. as companion animals, pets, livestock, and poultry. Insects such as Hemiptera (Hymenoptera), Diptera (Flyes), Hemiptera (Fleas), Haridae and Lice, etc., which have developed resistance to resistance, such as mites, mites, mites, and mites Tick such as mites, spider mites and tick mites, tick mites such as tick mites and giant tick mites, nematodes such as enopridae, roundworms, helminths, nematodes, roundworms, camaranus and antrum nematodes Can be effectively controlled with little adverse effect on target animals such as mammals and birds.

Claims (23)

Formula (1):


[In the formula, B represents a pyrazole ring represented by the following structural formula;


A ¹ Is -N (-O) _m2 Or -CR ¹ Represents
A ² Are D1-1 to D1-105, (Z ¹ ) _q Substituted with phenyl or (Z ¹ ) _q Represents naphthyl substituted with
R ¹ Is a hydrogen atom, halogen atom, cyano, nitro, C ₁ ~ C ₆ Alkyl, C ₁ ~ C ₆ Haloalkyl, C ₁ ~ C ₆ Alkoxy, C ₁ ~ C ₆ Haloalkoxy, C ₁ ~ C ₆ Alkylthio, C ₁ ~ C ₆ Alkylsulfinyl, C ₁ ~ C ₆ Alkylsulfonyl, C ₁ ~ C ₆ Haloalkylthio, C ₁ ~ C ₆ Haloalkylsulfinyl or C ₁ ~ C ₆ Represents haloalkylsulfonyl,
R ² Is a halogen atom, cyano, nitro, C ₁ ~ C ₆ Alkyl, C ₁ ~ C ₆ Haloalkyl, C ₁ ~ C ₆ Alkoxy, C ₁ ~ C ₆ Haloalkoxy, C ₁ ~ C ₆ Alkylthio, C ₁ ~ C ₆ Alkylsulfinyl, C ₁ ~ C ₆ Alkylsulfonyl, C ₁ ~ C ₆ Haloalkylthio, C ₁ ~ C ₆ Haloalkylsulfinyl or C ₁ ~ C ₆ Each represents R when haloalkylsulfonyl is represented and n1 represents an integer of 2 or more. ² May be the same or different from each other,
R ³ And R ⁴ Each independently represents a hydrogen atom, a halogen atom, or C ₁ ~ C ₆ Alkyl, C ₃ ~ C ₆ Cycloalkyl, C ₂ ~ C ₆ Alkenyl, C ₂ ~ C ₆ Alkynyl, C ₁ ~ C ₆ Haloalkyl, C ₁ ~ C ₆ Alkoxy, C ₁ ~ C ₆ Haloalkoxy, C ₁ ~ C ₆ Alkylthio, C ₁ ~ C ₆ Alkylsulfinyl, C ₁ ~ C ₆ Alkylsulfonyl, C ₁ ~ C ₆ Haloalkylthio, C ₁ ~ C ₆ Haloalkylsulfinyl, C ₁ ~ C ₆ Haloalkylsulfonyl, cyano, C ₁ ~ C ₆ Alkoxycarbonyl, C ₁ ~ C ₆ Alkylcarbonyl, C ₁ ~ C ₆ Alkylaminocarbonyl or di (C ₁ ~ C ₆ Alkyl) aminocarbonyl,
However, A ² Is D1-57, R ³ Is C ₁ ~ C ₆ Alkoxy, C ₁ ~ C ₆ Haloalkoxy, C ₁ ~ C ₆ Alkylthio, C ₁ ~ C ₆ Alkylsulfinyl, C ₁ ~ C ₆ Alkylsulfonyl, C ₁ ~ C ₆ Haloalkylthio, C ₁ ~ C ₆ Haloalkylsulfinyl, C ₁ ~ C ₆ Excluding haloalkylsulfonyl,
D1-1 to D1-105 each represent a ring represented by the following structural formula;








X ¹ Is a halogen atom, cyano, nitro, azide, -SCN, -SF ₅ , C ₁ ~ C ₁₂ Alkyl, R ⁵ Optionally substituted with (C ₁ ~ C ₁₂ ) Alkyl, C ₃ ~ C ₁₂ Cycloalkyl, R ⁵ Optionally substituted with (C ₃ ~ C ₁₂ ) Cycloalkyl, C ₂ ~ C ₁₂ Alkenyl, R ⁵ Optionally substituted with (C ₂ ~ C ₁₂ ) Alkenyl, C ₃ ~ C ₁₂ Cycloalkenyl, R ⁵ Optionally substituted with (C ₃ ~ C ₁₂ ) Cycloalkenyl, C ₂ ~ C ₁₂ Alkynyl, R ⁵ Optionally substituted with (C ₂ ~ C ₁₂ ) Alkynyl, C ₃ ~ C ₁₂ Allenyl, -OH, -OR ⁶ , -SH, -S (O) _r R ⁶ , -S (= NR ^8b ) R ^6a , -S (O) (= NR ^8b ) R ^6a , -N (R ^8a ) R ⁸ , -C (O) R ⁷ , -C (O) OH, -C (O) OR ^6a , -C (O) SR ^6a , -C (S) OR ^6a , -C (S) SR ^6a , -C (O) N (R ^8a ) R ⁸ , -C (S) N (R ^8a ) R ⁸ , -C (O) N (R ^8a ) N (R ^8a ) R ⁸ , -C (O) N (R ^8a ) OR ⁶ , -C (O) C (O) OR ^6a , -C (R ⁷ ) = NOH, -C (R ⁷ ) = NOR ⁶ , -C (R ⁷ ) = NN (R ^8a ) R ⁸ , -C (= NOR ⁶ ) N (R ^8a ) R ⁸ , -C (= NR ^8b ) OR ^6a , -C (= NR ^8b SR ^6a , -C (= NR ^8b ) N (R ^8a ) R ⁸ , -S (O) ₂ OR ⁶ , -S (O) ₂ N (R ^8a ) R ⁸ , -ON (R ^8a ) R ⁸ , -N (R ^8a ) OR ⁶ , -Si (R ^9a ) (R ^9b ) R ⁹ , -P (O) (OR ¹⁰ ) ₂ , -P (S) (OR ¹⁰ ) ₂ , -P (phenyl) ₂ , -P (O) (phenyl) ₂ , Phenyl, naphthyl, (Z ² ) _q2 Phenyl substituted with (Z ² ) _q2 Represents naphthyl or D2-1 to D2-102 substituted with, and when p1, p2, p4, p5, p6 or p8 represents an integer of 2 or more, each X ¹ May be the same as or different from each other, and two X ¹ Are adjacent, the two adjacent X ¹ Is -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 -, -CH ₂ CH ₂ CH ₂ CH ₂ -, -CH ₂ CH ₂ CH ₂ O-, -CH ₂ CH ₂ OCH ₂ -, -CH ₂ OCH ₂ O-, -OCH ₂ CH ₂ O-, -CH ₂ CH ₂ CH ₂ S- or -OCH ₂ CH ₂ By forming S-, each X ¹ May form a 5-membered ring or a 6-membered ring with the carbon atom to which is bonded, and the hydrogen atom bonded to each carbon atom forming the ring is X ² Optionally substituted by
Or A ² Are D1-1, D1-2, D1-5 to D1-17, D1-19, D1-20, D1-22 to D1-26, D1-28, D1-29, D1-36 to D1-40, D1 -42, D1-43, D1-46, D1-48, D1-52 to D1-57, D1-59 to D1-63, D1-67 to D1-70, D1-74, D1-80 to D1-87 , D1-94 to D1-96, D1-98, D1-99 or D1-103 to D1-105, and p1, p2, p3, p4, p5, p6 or p8 represents an integer of 1 or more, X ¹ When the carbon atom bonded to the carbon atom bonded to the 4-position of pyrazole represented by the formula (B) is adjacent, X ¹ Is R ³ Together with C ₂ ~ C ₄ Alkylene chain or C ₂ ~ C ₄ By forming an alkenylene chain, X ¹ Carbon atoms to which R ³ Carbon atoms to which ² A 6 to 8 membered ring may be formed together with the carbon atom to which the alkylene group is bonded. In this case, the alkylene chain or alkenylene chain may contain an oxygen atom, a sulfur atom or a nitrogen atom, and a halogen atom, a cyano group, a nitro group, C ₁ ~ C ₆ Alkyl group, C ₁ ~ C ₆ Haloalkyl group, C ₁ ~ C ₆ Alkoxy group, C ₁ ~ C ₆ Haloalkoxy group, C ₁ ~ C ₆ Alkylthio group, C ₁ ~ C ₆ Haloalkylthio group, -NH ₂ Group, C ₁ ~ C ₆ Alkylamino group, di (C ₁ ~ C ₆ ) Alkylamino group, phenyl, naphthyl, (Z ² ) _q2 Phenyl substituted with (Z ² ) _q2 Naphthyl or D2-1 to D2-102 substituted with oxo group, thioxo group, imino group, C ₁ ~ C ₆ An alkylimino group or C ₁ ~ C ₆ Optionally substituted by an alkoxyimino group or A ² Are D1-1, D1-2, D1-5 to D1-17, D1-19, D1-20, D1-22 to D1-26, D1-28, D1-29, D1-36 to D1-40, D1 -42, D1-43, D1-46, D1-48, D1-52 to D1-57, D1-59 to D1-63, D1-67 to D1-70, D1-74, D1-80 to D1-87 , D1-94 to D1-96, D1-98, D1-99 or D1-103 to D1-105, R ³ When represents methylene, R ³ Is R ³ And the carbon atom to which ² Carbon atoms to which ² May form a 5-membered ring with two carbon atoms forming R ³ Is a halogen atom, cyano group, nitro group, C ₁ ~ C ₆ Alkyl group, C ₁ ~ C ₆ Haloalkyl group, C ₁ ~ C ₆ Alkoxy group, C ₁ ~ C ₆ Haloalkoxy group, C ₁ ~ C ₆ Alkylthio group, C ₁ ~ C ₆ Haloalkylthio group, -NH ₂ Group, C ₁ ~ C ₆ Alkylamino group, di (C ₁ ~ C ₆ ) Alkylamino group, oxo group, thioxo group, imino group, C ₁ ~ C ₆ An alkylimino group or C ₁ ~ C ₆ Optionally substituted by an alkoxyimino group,
X ^1a Is a hydrogen atom, a halogen atom, cyano, nitro, azide, -SCN, -SF ₅ , C ₁ ~ C ₁₂ Alkyl, R ^5a Optionally substituted with (C ₁ ~ C ₁₂ ) Alkyl, C ₃ ~ C ₁₂ Cycloalkyl, R ^5a Optionally substituted with (C ₃ ~ C ₁₂ ) Cycloalkyl, C ₂ ~ C ₁₂ Alkenyl, R ^5a Optionally substituted with (C ₂ ~ C ₁₂ ) Alkenyl, C ₃ ~ C ₁₂ Cycloalkenyl, R ^5a Optionally substituted with (C ₃ ~ C ₁₂ ) Cycloalkenyl, C ₂ ~ C ₁₂ Alkynyl, R ^5a Optionally substituted with (C ₂ ~ C ₁₂ ) Alkynyl, C ₃ ~ C ₁₂ Allenyl, -OH, -OR ⁶ , -S (O) _r R ⁶ , -S (= NR ^8b ) R ^6a , -S (O) (= NR ^8b ) R ^6a , -N (R ^8a ) R ⁸ , -C (O) R ⁷ , -C (O) OR ^6a , -C (O) SR ^6a , -C (S) OR ^6a , -C (S) SR ^6a , -C (O) N (R ^8a ) R ⁸ , -C (S) N (R ^8a ) R ⁸ , -C (O) N (R ^8a ) N (R ^8a ) R ⁸ , -C (O) N (R ^8a ) OR ⁶ , -C (O) C (O) OR ^6a , -C (R ⁷ ) = NOH, -C (R ⁷ ) = NOR ⁶ , -C (R ⁷ ) = NN (R ^8a ) R ⁸ , -C (= NOR ⁶ ) N (R ^8a ) R ⁸ , -C (= NR ^8b ) OR ^6a , -C (= NR ^8b SR ^6a , -C (= NR ^8b ) N (R ^8a ) R ⁸ , -S (O) ₂ N (R ^8a ) R ⁸ , -Si (R ^9a ) (R ^9b ) R ⁹ , -P (O) (OR ¹⁰ ) ₂ , -P (S) (OR ¹⁰ ) ₂ , -P (phenyl) ₂ , -P (O) (phenyl) ₂ , Phenyl, naphthyl, (Z ² ) _q2 Phenyl substituted with (Z ² ) _q2 Represents naphthyl or D2-1 to D2-102 substituted with ^1a X next to ¹ Is adjacent X ^1a And X ¹ Is -CH ₂ CH ₂ O-, -CH ₂ CH ₂ CH ₂ CH ₂ -, -CH = CHCH = CH-, -N = CHCH = CH-, -CH = N-CH = CH-, -CH = CH-N = CH- or -CH = CH-CH = N-. X ^1a And X ¹ May form a 5- or 6-membered ring together with the atoms to which each is bonded, in which case the hydrogen atom bonded to each carbon atom forming the ring is a halogen atom, C ₁ ~ C ₆ Alkyl group or C ₁ ~ C ₆ Optionally substituted with a haloalkyl group or A ² X represents D1-6, D1-15, D1-25, D1-27, D1-40, D1-44, D1-47, D1-50, D1-73, D1-86 or D1-93, ^1a Is R ³ Together with C ₂ ~ C ₄ Alkylene chain or C ₂ ~ C ₄ By forming an alkenylene chain, X ^1a Nitrogen atom and R ³ Carbon atom to which is bonded and A ² May form a 6 to 8 membered ring together with the carbon atom to which is bonded, and in this case, the alkylene chain or alkenylene chain may contain 1 to 3 oxygen atoms, sulfur atoms or nitrogen atoms, and a halogen atom or cyano group , Nitro group, C ₁ ~ C ₆ Alkyl group, C ₁ ~ C ₆ Haloalkyl group, C ₁ ~ C ₆ Alkoxy group, C ₁ ~ C ₆ Haloalkoxy group, C ₁ ~ C ₆ Alkylthio group, C ₁ ~ C ₆ Haloalkylthio group, -NH ₂ Group, C ₁ ~ C ₆ Alkylamino group, di (C ₁ ~ C ₆ ) Alkylamino group, oxo group, thioxo group, imino group, C ₁ ~ C ₆ An alkylimino group or C ₁ ~ C ₆ Optionally substituted by an alkoxyimino group,
D2-1 to D2-102 each represent a ring represented by the following structural formula;








Z ¹ Is a halogen atom, cyano, nitro, azide, -SCN, -SF ₅ , C ₁ ~ C ₁₂ Alkyl, R ⁵ Optionally substituted with (C ₁ ~ C ₁₂ ) Alkyl, C ₃ ~ C ₁₂ Cycloalkyl, R ⁵ Optionally substituted with (C ₃ ~ C ₁₂ ) Cycloalkyl, C ₂ ~ C ₁₂ Alkenyl, R ⁵ Optionally substituted with (C ₂ ~ C ₁₂ ) Alkenyl, C ₃ ~ C ₁₂ Cycloalkenyl, R ⁵ Optionally substituted with (C ₃ ~ C ₁₂ ) Cycloalkenyl, C ₂ ~ C ₁₂ Alkynyl, R ⁵ Optionally substituted with (C ₂ ~ C ₁₂ ) Alkynyl, C ₃ ~ C ₁₂ Allenyl, -OH, -OR ⁶ , -SH, -S (O) _r R ⁶ , -S (= NR ^8b ) R ^6a , -S (O) (= NR ^8b ) R ^6a , -N (R ^8a ) R ⁸ , -C (O) R ⁷ , -C (O) OR ^6a , -C (O) SR ^6a , -C (S) OR ^6a , -C (S) SR ^6a , -C (O) N (R ^8a ) R ⁸ , -C (S) N (R ^8a ) R ⁸ , -C (O) N (R ^8a ) N (R ^8a ) R ⁸ , -C (O) N (R ^8a ) OR ⁶ , -C (O) C (O) OR ^6a , -C (R ⁷ ) = NOH, -C (R ⁷ ) = NOR ⁶ , -C (R ⁷ ) = NN (R ^8a ) R ⁸ , -C (= NOR ^6a ) N (R ^8a ) R ⁸ , -C (= NR ^8b ) OR ^6a , -C (= NR ^8b SR ^6a , -C (= NR ^8b ) N (R ^8a ) R ⁸ , -S (O) ₂ OR ^6a , -S (O) ₂ N (R ^8a ) R ⁸ , -ON (R ^8a ) R ⁸ , -N (R ^8a ) OR ⁶ , -Si (R ^9a ) (R ^9b ) R ⁹ , -P (O) (OR ¹⁰ ) ₂ , -P (S) (OR ¹⁰ ) ₂ , -P (phenyl) ₂ , P (O) (phenyl) ₂ , Phenyl, naphthyl, (Z ² ) _q2 Phenyl substituted with (Z ² ) _q2 Represents naphthyl substituted with D2-1 to D2-102, and when q represents an integer of 2 or more, each Z ¹ May be the same or different from each other, and two Z ¹ Are adjacent to each other, two adjacent Z ¹ Is -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 -, -CH ₂ CH ₂ N (X ^1a )-, -CH ₂ N (X ^1a ) CH ₂ -, -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-, -CH ₂ CH = CH-, -OCH = CH-, -SCH = CH-, -N (X ^1a ) CH = CH-, -OCH = N-, -SCH = N-, -N (X ^1a ) CH = N-, -N (X ^1a ) N = CH-, -OCH ₂ CH = CH-, -N = CHCH = CH-, -CH = NCH = CH-, -N = NCH = CH-, -CH = NN = CH-, -N = CHCH = N- or -N = CHN = By forming CH-, each Z ¹ May form a 5-membered ring or a 6-membered ring together with the carbon atom to which is bonded, and in this case, the hydrogen atom bonded to each carbon atom forming the ring is Z ² Or when q represents an integer of 1 or more, Z ¹ When the carbon atom bonded to the carbon atom bonded to the 4-position of pyrazole in formula (B) is adjacent, Z ¹ Is R ³ Together with C ₂ ~ C ₄ Alkylene chain or C ₂ ~ C ₄ By forming an alkenylene chain, Z ¹ Carbon atoms to which R ³ Carbon atoms to which ² A 6 to 8 membered ring may be formed together with the carbon atom to which the alkylene group is bonded. In this case, the alkylene chain or alkenylene chain may contain an oxygen atom, a sulfur atom or a nitrogen atom, and a halogen atom, a cyano group, a nitro group, C ₁ ~ C ₆ Alkyl group, C ₁ ~ C ₆ Haloalkyl group, C ₁ ~ C ₆ Alkoxy group, C ₁ ~ C ₆ Haloalkoxy group, C ₁ ~ C ₆ Alkylthio group, C ₁ ~ C ₆ Haloalkylthio group, -NH ₂ Group, C ₁ ~ C ₆ Alkylamino group, di (C ₁ ~ C ₆ ) Alkylamino group, oxo group, thioxo group, imino group, C ₁ ~ C ₆ An alkylimino group or C ₁ ~ C ₆ Optionally substituted by an alkoxyimino group,
R ⁵ And R ^5a Each independently represents a halogen atom, cyano, nitro, C ₃ ~ C ₈ Cycloalkyl, R ¹⁴ Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkyl, C ₃ ~ C ₈ Cycloalkenyl, R ¹⁴ Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkenyl, -OH, -OR ¹¹ , -SH, -S (O) _r R ¹¹ , -S (= NR ^13b ) R ^11a , -S (O) (= NR ^13b ) R ^11a , -N (R ^13a ) R ¹³ , -C (O) R ¹² , -C (O) OH, -C (O) OR ^11a , -C (O) SR ^11a , -C (S) OR ^11a , -C (S) SR ^11a , -C (O) N (R ^13a ) R ¹³ , -C (S) N (R ^13a ) R ¹³ , -C (O) N (R ^13a ) N (R ^13a ) R ¹³ , -C (O) N (R ^13a ) OR ¹¹ , -C (R ¹² ) = NOH, -C (R ¹² ) = NOR ¹¹ , -C (R ¹² ) = NN (R ^13a ) R ¹³ , -C (= NOR ^11a ) N (R ^13a ) R ¹³ , -C (= NR ^13b ) OR ^11a , -C (= NR ^13b SR ^11a , -C (= NR ^13b ) N (R ^13a ) R ¹³ , -S (O) ₂ N (R ^13a ) R ¹³ , -ON (R ^13a ) R ¹³ , -N (R ^13a ) OR ¹¹ , -Si (R ^9a ) (R ^9b ) R ⁹ , -P (O) (OR ¹⁰ ) ₂ , -P (S) (OR ¹⁰ ) ₂ , -P (phenyl) ₂ , -P (O) (phenyl) ₂ , Phenyl, naphthyl, (Z ² ) _q2 Phenyl substituted with (Z ² ) _q2 Represents naphthyl or D2-1 to D2-102 substituted with
R ⁶ Is C ₁ ~ C ₆ Alkyl, R ¹⁴ Optionally substituted with (C ₁ ~ C ₆ ) Alkyl, C ₃ ~ C ₈ Cycloalkyl, R ¹⁴ Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkyl, C ₂ ~ C ₆ Alkenyl, R ¹⁴ Optionally substituted with (C ₂ ~ C ₆ ) Alkenyl, C ₃ ~ C ₈ Cycloalkenyl, R ¹⁴ Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkenyl, C ₂ ~ C ₆ Alkynyl, R ¹⁴ Optionally substituted with (C ₂ ~ C ₆ ) Alkynyl, -S (O) ₂ R ^11a , -C (O) R ¹² , -C (O) OR ^11a , -C (O) SR ^11a , -C (S) OR ^11a , -C (S) SR ^11a , -C (O) N (R ^13a ) R ¹³ , -C (S) N (R ^13a ) R ¹³ , -S (O) ₂ N (R ^13a ) R ¹³ , -Si (R ^9a ) (R ^9b ) R ⁹ , -P (O) (OR ¹⁰ ) ₂ , -P (S) (OR ¹⁰ ) ₂ , -P (phenyl) ₂ , -P (O) (phenyl) ₂ , Phenyl, naphthyl, (Z ² ) _q2 Phenyl substituted with (Z ² ) _q2 Represents naphthyl or D2-1 to D2-102 substituted with
R ^6a Is C ₁ ~ C ₆ Alkyl, R ¹⁴ Optionally substituted with (C ₁ ~ C ₆ ) Alkyl, C ₃ ~ C ₈ Cycloalkyl, R ¹⁴ Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkyl, C ₂ ~ C ₆ Alkenyl, R ¹⁴ Optionally substituted with (C ₂ ~ C ₆ ) Alkenyl, C ₃ ~ C ₈ Cycloalkenyl, R ¹⁴ Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkenyl, C ₂ ~ C ₆ Alkynyl, R ¹⁴ Optionally substituted with (C ₂ ~ C ₆ ) Alkynyl, phenyl, naphthyl, (Z ² ) _q2 Phenyl substituted with (Z ² ) _q2 Represents naphthyl or D2-1 to D2-102 substituted with
R ⁷ Is a hydrogen atom or R ^6a Represents
R ⁸ And R ^8a Each independently represents a hydrogen atom, cyano, C ₁ ~ C ₆ Alkyl, R ¹⁴ Optionally substituted with (C ₁ ~ C ₆ ) Alkyl, C ₃ ~ C ₈ Cycloalkyl, R ¹⁴ Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkyl, C ₂ ~ C ₆ Alkenyl, R ¹⁴ Optionally substituted with (C ₂ ~ C ₆ ) Alkenyl, C ₃ ~ C ₈ Cycloalkenyl, R ¹⁴ Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkenyl, C ₂ ~ C ₆ Alkynyl, R ¹⁴ Optionally substituted with (C ₂ ~ C ₆ ) Alkynyl, -S (O) ₂ R ^11a , -C (O) R ¹² , -N (R ^13a ) R ¹³ , -C (O) OR ^11a , -C (O) SR ^11a , -C (S) OR ^11a , -C (O) N (R ^13a ) R ¹³ , -C (S) N (R ^13a ) R ¹³ , -S (O) ₂ N (R ^13a ) R ¹³ , -C (R ¹² ) = NOR ¹¹ , -C (R ¹² ) = NN (R ^13a ) R ¹³ , -C (= NOR ^11a ) N (R ^13a ) R ¹³ , -C (= NR ^13b ) OR ^11a , -C (= NR ^13b SR ^11a , -C (= NR ^13b ) N (R ^13a ) R ¹³ , -Si (R ^9a ) (R ^9b ) R ⁹ , -P (O) (OR ¹⁰ ) ₂ , -P (S) (OR ¹⁰ ) ₂ , -P (phenyl) ₂ , -P (O) (phenyl) ₂ , Phenyl, naphthyl, (Z ² ) _q2 Phenyl substituted with (Z ² ) _q2 Represents naphthyl or D2-1 to D2-102 substituted with R, or R ⁸ Is R ^8a Together with = C (R ^8c ) R ^8d , = S (R ^8e ) R ^8f Or = S (= O) (R ^8e ) R ^8f Or R ⁸ Is R ^8a Together with C ₂ ~ C ₇ By forming an alkylene chain of ⁸ And R ^8a May form a 3- to 8-membered ring together with the nitrogen atom to which is bonded, and in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and a halogen atom, C ₁ ~ C ₆ Alkyl group, C ₁ ~ C ₆ Haloalkyl group, C ₁ ~ C ₆ Alkoxy (C ₁ ~ C ₄ ) Alkyl group, C ₁ ~ C ₆ Alkoxy group, C ₁ ~ C ₆ Haloalkoxy group, C ₁ ~ C ₆ Alkylthio, C ₁ ~ C ₆ Alkylsulfinyl, C ₁ ~ C ₆ Alkylsulfonyl, C ₁ ~ C ₆ Haloalkylthio, C ₁ ~ C ₆ Haloalkylsulfinyl, C ₁ ~ C ₆ Haloalkylsulfonyl, -CHO group, C ₁ ~ C ₆ Alkoxycarbonyl group, C ₁ ~ C ₆ Haloalkoxycarbonyl group, C ₁ ~ C ₆ Alkylaminocarbonyl group, C ₁ ~ C ₆ Haloalkylaminocarbonyl group, phenyl group, (Z ² ) _q2 Optionally substituted by a phenyl group, D2-1 to D2-102, an oxo group or a thioxo group substituted by
R ^8b Is a hydrogen atom, cyano, nitro, C ₁ ~ C ₆ Alkyl, R ¹⁴ Optionally substituted with (C ₁ ~ C ₆ ) Alkyl, C ₃ ~ C ₈ Cycloalkyl, R ¹⁴ Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkyl, C ₂ ~ C ₆ Alkenyl, R ¹⁴ Optionally substituted with (C ₂ ~ C ₆ ) Alkenyl, C ₃ ~ C ₈ Cycloalkenyl, R ¹⁴ Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkenyl, C ₂ ~ C ₆ Alkynyl, R ¹⁴ Optionally substituted with (C ₂ ~ C ₆ ) Alkynyl, -S (O) ₂ R ¹¹ , -C (O) R ¹² , -C (O) OR ^11a , -C (O) SR ^11a , -C (S) OR ^11a , -C (S) SR ^11a , -C (S) SR ^11a , -C (O) N (R ^13a ) R ¹³ , -C (S) N (R ^13a ) R ¹³ , -S (O) ₂ N (R ^13a ) R ¹³ , -Si (R ^9a ) (R ^9b ) R ⁹ , -P (O) (OR ¹⁰ ) ₂ , -P (S) (OR ¹⁰ ) ₂ , -P (phenyl) ₂ , -P (O) (phenyl) ₂ , Phenyl, naphthyl, (Z ² ) _q2 Phenyl substituted with (Z ² ) _q2 Represents naphthyl or D2-1 to D2-102 substituted with
R ^8c Is a hydrogen atom, -OR ²⁰ , -S (O) _r R ²⁰ Or -N (R ^22a ) R ²² Represents
R ^8d Is C ₁ ~ C ₆ Alkyl, -OR ²⁰ , -S (O) _r R ²⁰ Or -N (R ^22a ) R ²² Or R ^8c And R ^8d Together C ₄ ~ C ₆ Alkylene chain or C ₄ ~ C ₆ By forming an alkenylene chain, R ^8c And R ^8d May form a 5- to 7-membered ring together with the carbon atom to which is bonded, and in this case, the alkylene chain or alkenylene chain may contain 1 to 3 oxygen atoms, sulfur atoms or nitrogen atoms, and a halogen atom or cyano group , Nitro group, C ₁ ~ C ₆ Alkyl group, C ₁ ~ C ₆ Haloalkyl group, C ₁ ~ C ₆ Alkoxy group, C ₁ ~ C ₆ Haloalkoxy group, C ₁ ~ C ₆ Alkylthio group or C ₁ ~ C ₆ Optionally substituted by a haloalkylthio group,
R ^8e And R ^8f Are each independently R ²³ Optionally substituted with (C ₁ ~ C ₆ ) Alkyl, R ²³ Optionally substituted with (C ₂ ~ C ₆ ) Alkenyl, R ²³ Optionally substituted with (C ₂ ~ C ₆ ) Alkynyl, R ²³ Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkyl, C ₁ ~ C ₆ Alkyl, C ₂ ~ C ₆ Alkenyl, C ₃ ~ C ₆ Alkynyl, C ₃ ~ C ₈ Cycloalkyl, C ₁ ~ C ₆ Haloalkyl, C ₂ ~ C ₆ Haloalkenyl, C ₃ ~ C ₆ Haloalkynyl, C ₃ ~ C ₈ Halocycloalkyl, phenyl, naphthyl, (Z ² ) _q2 Phenyl substituted with (Z ² ) _q2 Represents naphthyl or D2-1 to D2-102 substituted with R, or R ^8e And R ^8f Together C ₄ ~ C ₆ Alkylene chain or C ₄ ~ C ₆ By forming an alkenylene chain, R ^8e And R ^8f May form a 5- to 7-membered ring together with the sulfur atom to which is bonded, and in this case, the alkylene chain or alkenylene chain may contain 1 to 3 oxygen atoms, sulfur atoms or nitrogen atoms, and a halogen atom or cyano group , Nitro group, C ₁ ~ C ₆ Alkyl group, C ₁ ~ C ₆ Haloalkyl group, C ₁ ~ C ₆ Alkoxy group, C ₁ ~ C ₆ Haloalkoxy group, C ₁ ~ C ₆ Alkylthio group or C ₁ ~ C ₆ Optionally substituted by a haloalkylthio group,
R ⁹ , R ^9a And R ^9b Are each independently a hydrogen atom, C ₁ ~ C ₆ Alkyl, C ₁ ~ C ₆ Haloalkyl, C ₁ ~ C ₆ Alkoxy, C ₁ ~ C ₆ Haloalkoxy, C ₁ ~ C ₆ Alkylcarbonyl, C ₁ ~ C ₆ Haloalkylcarbonyl, C ₁ ~ C ₆ Alkoxycarbonyl, C ₁ ~ C ₆ Haloalkoxycarbonyl, phenyl or (Z ² ) _q2 Represents phenyl substituted with
R ¹⁰ Is a hydrogen atom or C ₁ ~ C ₆ Represents alkyl,
R ¹¹ Is cyano, C ₁ ~ C ₆ Alkyl, R ^14a Optionally substituted with (C ₁ ~ C ₆ ) Alkyl, C ₂ ~ C ₆ Alkenyl, R ^14a Optionally substituted with (C ₂ ~ C ₆ ) Alkenyl, C ₂ ~ C ₆ Alkynyl, R ^14a Optionally substituted with (C ₂ ~ C ₆ ) Alkynyl, C ₃ ~ C ₈ Cycloalkyl, R ^14a Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkyl, C ₃ ~ C ₈ Cycloalkenyl, R ^14a Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkenyl, phenyl, naphthyl, (Z ² ) _q2 Phenyl substituted with (Z ² ) _q2 Substituted with naphthyl, D2-1 to D2-102, -S (O) ₂ R ^15a , -C (O) R ¹⁶ , -C (O) OR ^15a , -C (O) SR ^15a , -C (S) OR ^15a , -C (S) SR ^15a , -C (O) N (R ^17a ) R ¹⁷ , -C (S) N (R ^17a ) R ¹⁷ , -S (O) ₂ N (R ^17a ) R ¹⁷ , -Si (R ^9a ) (R ^9b ) R ⁹ , -P (O) (OR ¹⁰ ) ₂ Or -P (S) (OR ¹⁰ ) ₂ Represents
R ^11a Is C ₁ ~ C ₆ Alkyl, R ^14a Optionally substituted with (C ₁ ~ C ₆ ) Alkyl, C ₂ ~ C ₆ Alkenyl, R ^14a Optionally substituted with (C ₂ ~ C ₆ ) Alkenyl, C ₂ ~ C ₆ Alkynyl, R ^14a Optionally substituted with (C ₂ ~ C ₆ ) Alkynyl, C ₃ ~ C ₈ Cycloalkyl, R ^14a Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkyl, C ₃ ~ C ₈ Cycloalkenyl, R ^14a Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkenyl, phenyl, naphthyl, (Z ² ) _q2 Phenyl substituted with (Z ² ) _q2 Represents naphthyl or D2-1 to D2-102 substituted with
R ¹² Is a hydrogen atom or R ^11a Represents
R ¹³ And R ^13a Each independently represents a hydrogen atom, cyano, C ₁ ~ C ₆ Alkyl, R ^14a Optionally substituted with (C ₁ ~ C ₆ ) Alkyl, C ₂ ~ C ₆ Alkenyl, R ^14a Optionally substituted with (C ₂ ~ C ₆ ) Alkenyl, C ₂ ~ C ₆ Alkynyl, R ^14a Optionally substituted with (C ₂ ~ C ₆ ) Alkynyl, C ₃ ~ C ₈ Cycloalkyl, R ^14a Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkyl, C ₃ ~ C ₈ Cycloalkenyl, R ^14a Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkenyl, phenyl, naphthyl, (Z ² ) _q2 Phenyl substituted with (Z ² ) _q2 Substituted with naphthyl, D2-1 to D2-102, -S (O) _r R ¹⁵ , -N (R ^17a ) R ¹⁷ , -C (O) R ¹⁶ , -C (O) OR ^15a , -C (O) SR ^15a , -C (S) OR ^15a , -C (S) SR ^15a , -C (O) N (R ^17a ) R ¹⁷ , -C (S) N (R ^17a ) R ¹⁷ , -S (O) ₂ N (R ^17a ) R ¹⁷ , -C (R ¹⁶ ) = NOR ^15a , -C (R ¹⁶ ) = NN (R ^17a ) R ¹⁷ , -C (= NOR ^15a ) N (R ^17a ) R ¹⁷ , -C (= NR ^17b ) OR ^15a , -C (= NR ^17b SR ^15a , -C (= NR ^17b ) N (R ^17a ) R ¹⁷ , -Si (R ^9a ) (R ^9b ) R ⁹ , -P (O) (OR ¹⁰ ) ₂ Or -P (S) (OR ¹⁰ ) ₂ Or R ¹³ Is R ^13a Together with = C (R ^8c ) R ^8d , = S (R ^8e ) R ^8f Or = S (= O) (R ^8e ) R ^8f Or R ¹³ Is R ^13a Together with C ₂ ~ C ₇ By forming an alkylene chain of ¹³ And R ^13a May form a 3- to 8-membered ring together with the nitrogen atom to which is bonded, and in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and a halogen atom, C ₁ ~ C ₆ Alkyl group, C ₁ ~ C ₆ Haloalkyl group, C ₁ ~ C ₆ Alkoxy (C ₁ ~ C ₄ ) Alkyl group, C ₁ ~ C ₆ Alkoxy group, -CHO group, C ₁ ~ C ₆ Alkoxycarbonyl group, C ₁ ~ C ₆ Haloalkoxycarbonyl group, C ₁ ~ C ₆ Alkylaminocarbonyl group, C ₁ ~ C ₆ Haloalkylaminocarbonyl group, phenyl group, (Z ² ) _q2 Optionally substituted by a phenyl group, D2-1 to D2-102, an oxo group or a thioxo group substituted by
R ^13b Is a hydrogen atom, cyano, nitro, C ₁ ~ C ₆ Alkyl, R ^14a Optionally substituted with (C ₁ ~ C ₆ ) Alkyl, C ₂ ~ C ₆ Alkenyl, R ^14a Optionally substituted with (C ₂ ~ C ₆ ) Alkenyl, C ₂ ~ C ₆ Alkynyl, R ^14a Optionally substituted with (C ₂ ~ C ₆ ) Alkynyl, C ₃ ~ C ₈ Cycloalkyl, R ^14a Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkyl, C ₃ ~ C ₈ Cycloalkenyl, R ^14a Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkenyl, -S (O) _r R ¹⁵ , -C (O) R ¹⁶ , -C (O) OR ^15a , -C (O) N (R ^17a ) R ¹⁷ , -C (S) N (R ^17a ) R ¹⁷ , -S (O) ₂ N (R ^17a ) R ¹⁷ , -Si (R ^9a ) (R ^9b ) R ⁹ , -P (O) (OR ¹⁰ ) ₂ , -P (S) (OR ¹⁰ ) ₂ , Phenyl, naphthyl, (Z ² ) _q2 Phenyl substituted with (Z ² ) _q2 Represents naphthyl or D2-1 to D2-102 substituted with
R ¹⁴ And R ^14a Each independently represents a halogen atom, cyano, nitro, C ₃ ~ C ₈ Cycloalkyl, R ¹⁸ Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkyl, C ₃ ~ C ₈ Cycloalkenyl, R ¹⁸ Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkenyl, -OH, -OR ¹⁵ , -SH, -S (O) _r R ¹⁵ , -S (= NR ^17b ) R ^15a , -S (O) (= NR ^17b ) R ^15a , -N (R ^17a ) R ¹⁷ , -C (O) R ¹⁶ , -C (O) OH, -C (O) OR ^15a , -C (O) SR ^15a , -C (S) OR ^15a , -C (S) SR ^15a , -C (O) N (R ^17a ) R ¹⁷ , -C (S) N (R ^17a ) R ¹⁷ , -C (O) N (R ^17a ) N (R ^17a ) R ¹⁷ , -C (O) N (R ^17a ) OR ^15a , -C (R ¹⁶ ) = NOH, -C (R ¹⁶ ) = NOR ^15a , -C (R ¹⁶ ) = NN (R ^17a ) R ¹⁷ , -C (= NOR ^15a ) N (R ^17a ) R ¹⁷ , -C (= NR ^17b ) OR ^15a , -C (= NR ^17b SR ^15a , -C (= NR ^17b ) N (R ^17a ) R ¹⁷ , -S (O) ₂ N (R ^17a ) R ¹⁷ , -ON (R ^17a ) R ¹⁷ , -N (R ^17a ) OR ^15a , -Si (R ^9a ) (R ^9b ) R ⁹ , -P (O) (OR ¹⁰ ) ₂ , -P (S) (OR ¹⁰ ) ₂ , -P (phenyl) ₂ , -P (O) (phenyl) ₂ , Phenyl, naphthyl, (Z ² ) _q2 Phenyl substituted with (Z ² ) _q2 Represents naphthyl or D2-1 to D2-102 substituted with
R ¹⁵ Is phenyl, naphthyl, (Z ² ) _q2 Phenyl substituted with (Z ² ) _q2 Substituted with naphthyl, D2-1 to D2-102, C ₁ ~ C ₆ Alkyl, R ¹⁹ Optionally substituted with (C ₁ ~ C ₆ ) Alkyl, C ₂ ~ C ₆ Alkenyl, R ¹⁹ Optionally substituted with (C ₂ ~ C ₆ ) Alkenyl, C ₂ ~ C ₆ Alkynyl, R ¹⁹ Optionally substituted with (C ₂ ~ C ₆ ) Alkynyl, C ₃ ~ C ₈ Cycloalkyl, R ¹⁹ Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkyl, C ₃ ~ C ₈ Cycloalkenyl, R ¹⁹ Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkenyl, -S (O) ₂ R ²⁰ , -C (O) R ²¹ , -C (O) OR ²⁰ , -C (O) SR ²⁰ , -C (S) OR ²⁰ , -C (S) SR ²⁰ , -C (O) N (R ^22a ) R ²² , -C (S) N (R ^22a ) R ²² , -S (O) ₂ N (R ^22a ) R ²² , -Si (R ^9a ) (R ^9b ) R ⁹ , -P (O) (OR ¹⁰ ) ₂ Or -P (S) (OR ¹⁰ ) ₂ Represents
R ^15a Is phenyl, naphthyl, (Z ² ) _q2 Phenyl substituted with (Z ² ) _q2 Substituted with naphthyl, D2-1 to D2-102, C ₁ ~ C ₆ Alkyl, R ¹⁹ Optionally substituted with (C ₁ ~ C ₆ ) Alkyl, C ₂ ~ C ₆ Alkenyl, R ¹⁹ Optionally substituted with (C ₂ ~ C ₆ ) Alkenyl, C ₃ ~ C ₈ Cycloalkenyl, R ¹⁹ Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkenyl, C ₂ ~ C ₆ Alkynyl, R ¹⁹ Optionally substituted with (C ₂ ~ C ₆ ) Alkynyl, C ₃ ~ C ₈ Cycloalkyl or R ¹⁹ Optionally substituted with (C ₃ ~ C ₈ ) Represents cycloalkyl,
R ¹⁶ Is a hydrogen atom or R ¹⁵ Represents
R ¹⁷ And R ^17a Each independently represents a hydrogen atom, cyano, -CHO, -S (O). _r R ²⁰ , -N (R ^22a ) R ²² , -C (O) R ²¹ , -C (O) OR ²⁰ , -C (O) SR ²⁰ , -C (S) OR ²⁰ , -C (S) SR ²⁰ , -C (O) N (R ^22a ) R ²² , -C (S) N (R ^22a ) R ²² , -S (O) ₂ N (R ^22a ) R ²² , -C (R ^21a ) = NOR ²⁰ , -C (R ^21a ) = NN (R ^22a ) R ²² , -C (= NOR ²⁰ ) N (R ^22a ) R ²² , -C (= NR ^22b ) OR ^20a , -C (= NR ^22b SR ^20a , -C (= NR ^22b ) N (R ^22a ) R ²² , -Si (R ^9a ) (R ^9b ) R ⁹ , -P (O) (OR ¹⁰ ) ₂ , -P (S) (OR ¹⁰ ) ₂ , Phenyl, naphthyl, (Z ² ) _q2 Phenyl substituted with (Z ² ) _q2 Substituted with naphthyl, D2-1 to D2-102, C ₁ ~ C ₆ Alkyl, R ¹⁹ Optionally substituted with (C ₁ ~ C ₆ ) Alkyl, C ₂ ~ C ₆ Alkenyl, R ¹⁹ Optionally substituted with (C ₂ ~ C ₆ ) Alkenyl, C ₃ ~ C ₈ Cycloalkenyl, R ¹⁹ Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkenyl, C ₂ ~ C ₆ Alkynyl, R ¹⁹ Optionally substituted with (C ₂ ~ C ₆ ) Alkynyl, C ₃ ~ C ₈ Cycloalkyl or R ¹⁹ Optionally substituted with (C ₃ ~ C ₈ ) Represents cycloalkyl or R ¹⁷ Is R ^17a Together with = C (R ^8c ) R ^8d , = S (R ^8e ) R ^8f Or = S (= O) (R ^8e ) R ^8f Or R ¹⁷ Is R ^17a Together with C ₂ ~ C ₇ By forming an alkylene chain of ¹⁷ And R ^17a May form a 3- to 8-membered ring together with the nitrogen atom to which is bonded, and in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and a halogen atom, C ₁ ~ C ₆ Alkyl group, C ₁ ~ C ₆ Haloalkyl group, C ₁ ~ C ₆ Alkoxy (C ₁ ~ C ₄ ) Alkyl group, C ₁ ~ C ₆ Alkoxy group, -CHO group, C ₁ ~ C ₆ Alkoxycarbonyl group, C ₁ ~ C ₆ Haloalkoxycarbonyl group, C ₁ ~ C ₆ Alkylaminocarbonyl group, C ₁ ~ C ₆ Haloalkylaminocarbonyl group, phenyl group, (Z ² ) _q2 Optionally substituted by a phenyl group, D2-1 to D2-102, an oxo group or a thioxo group substituted by
R ^17b Is a hydrogen atom, cyano, nitro, -CHO, -S (O) _r R ²⁰ , -C (O) R ²¹ , -C (O) OR ²⁰ , -C (O) N (R ^22a ) R ²² , -C (S) N (R ^22a ) R ²² , -S (O) ₂ N (R ^22a ) R ²² , -Si (R ^9a ) (R ^9b ) R ⁹ , -P (O) (OR ¹⁰ ) ₂ , -P (S) (OR ¹⁰ ) ₂ , Phenyl, naphthyl, (Z ² ) _q2 Phenyl substituted with (Z ² ) _q2 Substituted with naphthyl, D2-1 to D2-102, C ₁ ~ C ₆ Alkyl, R ¹⁹ Optionally substituted with (C ₁ ~ C ₆ ) Alkyl, C ₂ ~ C ₆ Alkenyl, R ¹⁹ Optionally substituted with (C ₂ ~ C ₆ ) Alkenyl, C ₃ ~ C ₈ Cycloalkenyl, R ¹⁹ Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkenyl, C ₂ ~ C ₆ Alkynyl, R ¹⁹ Optionally substituted with (C ₂ ~ C ₆ ) Alkynyl, C ₃ ~ C ₈ Cycloalkyl or R ¹⁹ Optionally substituted with (C ₃ ~ C ₈ ) Represents cycloalkyl,
R ¹⁸ And R ¹⁹ Each independently represents a halogen atom, cyano, nitro, phenyl, naphthyl, (Z ² ) _q2 Phenyl substituted with (Z ² ) _q2 Substituted with naphthyl, D2-1 to D2-102, C ₃ ~ C ₈ Cycloalkyl, C ₃ ~ C ₈ Halocycloalkyl, C ₃ ~ C ₈ Cycloalkenyl, C ₃ ~ C ₈ Halocycloalkenyl, C ₁ ~ C ₆ Alkoxy, C ₁ ~ C ₆ Haloalkoxy, C ₁ ~ C ₆ Alkylthio, C ₁ ~ C ₆ Haloalkylthio, C ₁ ~ C ₆ Alkylsulfinyl, C ₂ ~ C ₆ Alkenylsulfinyl, C ₁ ~ C ₆ Haloalkylsulfinyl, C ₁ ~ C ₆ Alkylsulfonyl, C ₁ ~ C ₆ Haloalkylsulfonyl, C ₁ ~ C ₆ Alkylcarbonyl, C ₁ ~ C ₆ Haloalkylcarbonyl, C ₁ ~ C ₆ Alkoxycarbonyl, C ₁ ~ C ₆ Haloalkoxycarbonyl, C ₁ ~ C ₆ Alkylaminocarbonyl, C ₁ ~ C ₆ Haloalkylaminocarbonyl, di (C ₁ ~ C ₆ Alkyl) aminocarbonyl, OR ²³ , S (O) _r R ²³ Or C (O) R ²³ Represents
R ²⁰ , R ^20a , R ²¹ And R ^21a Are each independently phenyl, naphthyl, (Z ² ) _q2 Phenyl substituted with (Z ² ) _q2 Naphthyl substituted with D2-1 to D2-102, R ²³ Optionally substituted with (C ₁ ~ C ₆ ) Alkyl, R ²³ Optionally substituted with (C ₂ ~ C ₆ ) Alkenyl, R ²³ Optionally substituted with (C ₂ ~ C ₆ ) Alkynyl, R ²³ Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkyl, R ²³ Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkenyl, C ₁ ~ C ₆ Alkyl, C ₂ ~ C ₆ Alkenyl, C ₂ ~ C ₆ Alkynyl, C ₃ ~ C ₈ Cycloalkyl, C ₁ ~ C ₆ Haloalkyl, C ₂ ~ C ₆ Haloalkenyl, C ₂ ~ C ₆ Haloalkynyl, C ₃ ~ C ₈ Halocycloalkyl or C ₃ ~ C ₈ Represents halocycloalkenyl,
R ²² And R ^22a Each independently represents a hydrogen atom, cyano, —CHO, phenyl, naphthyl, (Z ² ) _q2 Phenyl substituted with (Z ² ) _q2 Naphthyl substituted with D2-1 to D2-102, R ²³ Optionally substituted with (C ₁ ~ C ₆ ) Alkyl, R ²³ Optionally substituted with (C ₂ ~ C ₆ ) Alkenyl, R ²³ Optionally substituted with (C ₂ ~ C ₆ ) Alkynyl, R ²³ Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkyl, R ²³ Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkenyl, C ₁ ~ C ₆ Alkyl, C ₂ ~ C ₆ Alkenyl, C ₂ ~ C ₆ Alkynyl, C ₃ ~ C ₈ Cycloalkyl, C ₁ ~ C ₆ Haloalkyl, C ₂ ~ C ₆ Haloalkenyl, C ₂ ~ C ₆ Haloalkynyl, C ₃ ~ C ₈ Halocycloalkyl, C ₃ ~ C ₈ Halocycloalkenyl, C ₁ ~ C ₆ Alkylsulfonyl, C ₁ ~ C ₆ Haloalkylsulfonyl, C ₁ ~ C ₆ Alkylcarbonyl, C ₁ ~ C ₆ Haloalkylcarbonyl, C ₁ ~ C ₆ Alkoxycarbonyl, C ₁ ~ C ₆ Haloalkoxycarbonyl, -OR ²³ , -S (O) _r R ²³ Or -C (O) R ²³ Represents
R ^22b Is R ²² Or represents nitro,
R ²³ Is phenyl, naphthyl, (Z ² ) _q2 Phenyl substituted with (Z ² ) _q2 Represents naphthyl or D2-1 to D2-102 substituted with
X ² Is a halogen atom, cyano, nitro, -OH, -SH, -NH ₂ , -C (O) NH ₂ , -C (S) NH ₂ , -S (O) ₂ NH ₂ Or R ²⁴ When t1, t2 or t4 represents an integer of 2 or more, each X ² May be the same as or different from each other, and two X ² Are adjacent, the two adjacent X ² Is -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 -, -CH ₂ CH ₂ CH ₂ CH ₂ -, -CH ₂ CH ₂ CH ₂ O-, -CH ₂ CH ₂ OCH ₂ -, -CH ₂ OCH ₂ O-, -OCH ₂ CH ₂ O-, -CH ₂ CH ₂ CH ₂ S- or -OCH ₂ CH ₂ By forming S-, each X ² May form a 5-membered ring or a 6-membered ring together with the carbon atom to which is bonded, and the hydrogen atom bonded to each carbon atom forming the ring is a halogen atom, C ₁ ~ C ₆ Alkyl group, C ₁ ~ C ₆ Haloalkyl group, C ₁ ~ C ₆ Alkoxy group, C ₁ ~ C ₆ Alkylthio group, C ₁ ~ C ₆ An alkylsulfinyl group or C ₁ ~ C ₆ Optionally substituted by an alkylsulfonyl group,
X ^2a Is a hydrogen atom, cyano, -OH, -NH ₂ , -CHO or R ²⁴ X ^2a X next to ² Is adjacent X ^2a And X ² Is -CH ₂ CH ₂ CH ₂ CH ₂ -, -CH = CHCH = CH-, -N = CHCH = CH-, -CH = N-CH = CH-, -CH = CH-N = CH- or -CH = CH-CH = N-. X ^2a And X ² May form a 6-membered ring together with the atoms to which each of them is bonded, and at this time, the hydrogen atom bonded to each carbon atom forming the ring is a halogen atom, C ₁ ~ C ₆ Alkyl group, C ₁ ~ C ₆ Haloalkyl group, C ₁ ~ C ₆ Alkoxy group, C ₁ ~ C ₆ Alkylthio group, C ₁ ~ C ₆ An alkylsulfinyl group or C ₁ ~ C ₆ Optionally substituted by an alkylsulfonyl group,
X ^2b Is a halogen atom, cyano, nitro, -OH, -SH, -NH ₂ , -C (O) NH ₂ , -C (S) NH ₂ , -S (O) ₂ NH ₂ , -CHO or R ²⁴ When u1, u2, u4, u5, u6, u7, u8 or u9 represents an integer of 2 or more, each X ^2b May be the same as or different from each other, and two X ^2b Are substituted on the same carbon, two X ^2b Together oxo, thioxo, imino, C ₁ ~ C ₆ Alkylimino, C ₁ ~ C ₆ Alkoxyimino or C ₁ ~ C ₆ May form alkylidene,
Z ² Is a halogen atom, cyano, nitro, -OH, -SH, -NH ₂ , -C (O) NH ₂ , -C (S) NH ₂ , -S (O) ₂ NH ₂ Or R ²⁴ And when q2 represents an integer of 2 or more, each Z ² May be the same as or different from each other, and two Z ² Are adjacent to each other, two adjacent Z ² Is -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 -, -CH ₂ CH ₂ N (X ^2a )-, -CH ₂ N (X ^2a ) CH ₂ -, -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-, -CH ₂ CH = CH-, -OCH = CH-, -SCH = CH-, -N (X ^2a ) CH = CH-, -OCH = N-, -SCH = N-, -N (X ^2a ) CH = N-, -N (X ^2a ) N = CH-, -OCH ₂ CH = CH-, -N = CHCH = CH-, -CH = NCH = CH-, -N = NCH = CH-, -CH = NN = CH-, -N = CHCH = N- or -N = CHN = By forming CH-, each Z ² May form a 5-membered ring or a 6-membered ring together with the carbon atom to which is bonded, and at this time, the hydrogen atom bonded to each carbon atom forming the ring is a halogen atom, C ₁ ~ C ₆ Alkyl group, C ₁ ~ C ₆ Haloalkyl group, C ₁ ~ C ₆ Alkoxy group, C ₁ ~ C ₆ Alkylthio group, C ₁ ~ C ₆ An alkylsulfinyl group or C ₁ ~ C ₆ Optionally substituted by an alkylsulfonyl group,
R ²⁴ Is C ₁ ~ C ₆ Alkyl, C ₂ ~ C ₆ Alkenyl, C ₂ ~ C ₆ Alkynyl, C ₃ ~ C ₈ Cycloalkyl, R ²⁸ Optionally substituted with (C ₁ ~ C ₆ ) Alkyl, R ²⁸ Optionally substituted with (C ₂ ~ C ₆ ) Alkenyl, R ²⁸ Optionally substituted with (C ₂ ~ C ₆ ) Alkynyl, R ²⁸ Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkyl, R ²⁸ Optionally substituted with (C ₃ ~ C ₈ ) Cycloalkenyl, -OR ²⁵ , -S (O) _r R ²⁵ , -C (O) OR ²⁵ , -C (O) R ²⁶ , -N (R ^27a ) R ²⁷ , -C (O) N (R ^27a ) R ²⁷ , -C (S) N (R ^27a ) R ²⁷ , -S (O) _r N (R ^27a ) R ²⁷ , Phenyl, C ₁ ~ C ₆ Represents phenyl optionally substituted with an alkyl or halogen atom;
R ²⁵ , R ²⁶ And R ^27a Are each independently a hydrogen atom, C ₁ ~ C ₆ Alkyl, C ₁ ~ C ₆ Haloalkyl, C ₃ ~ C ₈ Represents cycloalkyl,
R ²⁷ Is a hydrogen atom, C ₁ ~ C ₆ Alkyl, C ₁ ~ C ₆ Haloalkyl, C ₃ ~ C ₈ Cycloalkyl, C ₁ ~ C ₆ Alkylcarbonyl, C ₃ ~ C ₈ Cycloalkylcarbonyl, C ₁ ~ C ₆ Haloalkylcarbonyl, C ₁ ~ C ₆ Alkoxycarbonyl, C ₁ ~ C ₆ Haloalkoxycarbonyl
Represents
R ²⁸ Is a halogen atom, cyano, nitro, C ₁ ~ C ₆ Alkoxy, C ₁ ~ C ₆ Haloalkoxy, C ₁ ~ C ₆ Alkylthio, C ₁ ~ C ₆ Haloalkylthio, C ₁ ~ C ₆ Alkylsulfinyl, C ₁ ~ C ₆ Haloalkylsulfinyl, C ₁ ~ C ₆ Alkylsulfonyl, C ₁ ~ C ₆ Haloalkylsulfonyl, C ₁ ~ C ₆ Alkylcarbonyl, C ₃ ~ C ₈ Cycloalkylcarbonyl, C ₁ ~ C ₆ Haloalkylcarbonyl, C ₁ ~ C ₆ Alkoxycarbonyl, C ₁ ~ C ₆ Haloalkoxycarbonyl, C ₁ ~ C ₆ Alkylaminosulfonyl, di (C ₁ ~ C ₆ Alkyl) aminosulfonyl, C ₁ ~ C ₆ Alkylamino, di (C ₁ ~ C ₆ Alkyl) amino,
n1, p1, t1, and u1 each independently represents an integer of 0 to 3,
p2, t2 and u2 each independently represent an integer of 0 to 2,
p3 and t3 each independently represents an integer of 0 to 1,
p4, t4 and u4 each independently represent an integer of 0 to 4,
p5 and u5 each independently represent an integer of 0 to 5;
p6 and u6 each independently represent an integer of 0 to 6;
u7 each independently represents an integer of 0 to 7,
p8 represents an integer of 1 to 4,
u8 represents an integer of 0 to 8,
u9 represents an integer of 0 to 9,
q and q2 each independently represent an integer of 1 to 5,
m1, m2, m3 and m4 each independently represents an integer of 0 or 1,
r represents an integer of 0-2. ] The parasite control composition of the animal which contains the pyrazole derivative represented by these, or its salt as an active ingredient. (1) ^{A 2} is, D1-1~D1-5, D1-8~D1-14, D1-18~D1-24, D1-28~D1-38 , D1-41, D1-43, D1-46 D1-48, D1-49, D1-52 to D1-68, D1-70 to D1-72, D1-74 to D1-76, D1-79, D1-82 to D1-85, D1-88, D1 -89, D1-91, D1-92 or D1-94 to D1-105, and p1, p2, p3, p4, p5, p6 or p8 represents an integer of 1 or more,
X ¹ is a halogen atom, cyano, nitro, azide, —SCN, —SF ₅ , C ₁ -C ₁₂ alkyl, (C ₁ -C ₁₂ ) alkyl optionally substituted with R ⁵ , C ₃ -C ₁₂ cyclo. alkyl, optionally substituted with ^{R 5} _(C 3 ~C _{12) cycloalkyl,} C 2 _{-C 12} alkenyl, optionally substituted with ^{R 5} _(C 2 ~C _{12) alkenyl,} C 3 _{-C 12} cycloalkyl alkenyl, optionally substituted with ^{R 5} _(C 3 ~C _{12) cycloalkenyl,} C 2 _{-C 12} alkynyl, optionally substituted with ^{R 5} _(C 2 ~C _{12) alkynyl,} C 3 _{-C 12} allenyl _{^{, -OH, -OR 6, -SH,}} -S (O) r R 6, -S (= NR 8b) R 6a, -S (O) (= NR 8b) R 6a, -N (R 8a) R ^{8, -C (O) R 7} , -C (O) ^{H, -C (O) OR 6a} , -C (O) SR 6a, -C (S) OR 6a, -C (S) SR 6a, -C (O) N (R 8a) R 8, -C ( ^{S) N (R 8a) R} 8, -C (O) N (R 8a) N (R 8a) R 8, -C (O) N (R 8a) OR 6, -C (O) C (O) OR ^6a , -C (R ⁷ ) = NOH, -C (R ⁷ ) = NOR ⁶ , -C (R ⁷ ) = NN (R ^8a ) R ⁸ , -C (= NOR ⁶ ) N (R ^8a ) R ^{8, -C (= NR 8b)} OR 6a, -C (= NR 8b) SR 6a, -C (= NR 8b) N (R 8a) R 8, -S (O) 2 OR 6, -S (O ) ₂ N (R ^8a ) R ⁸ , -ON (R ^8a ) R ⁸ , -N (R ^8a ) OR ⁶ , -Si (R ^9a ) (R ^9b ) R ⁹ , -P (O) (OR ¹⁰ ) _2, -P (S ^(OR ₁₀₎ 2, -P _(phenyl) 2, -P (O) _{(phenyl) 2,} phenyl, ^naphthyl, (Z ₂₎ phenyl substituted with ^_q2, (Z ₂₎ is substituted with _q2 naphthyl or D2 -1 to D2-102, and when p1, p2, p4, p5, p6 or p8 represents an integer of 2 or more, each X ¹ may be the same as or different from each other; When two X ¹ are adjacent to each other, the two adjacent X ¹ 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 -, - CH 2 CH 2 CH 2 CH 2 -, - CH 2 CH 2 CH 2 O -, - CH 2 CH 2 OCH 2 -, - CH 2 OCH 2 O _{-, - OCH 2 CH 2 O} -, - CH 2 C By forming H ₂ CH ₂ S— or —OCH ₂ CH ₂ S—, a 5-membered ring or a 6-membered ring may be formed together with the carbon atom to which each X ¹ is bonded. The hydrogen atom bonded to each carbon atom may be optionally replaced by X ² ;
(Provided that one or more of ^X 1 _{^{are, -S (O) r R 11}} , -S (= NR 13b) R 11a, -S (O) (= NR 13b) R 11a, -C (R 12) = NOH and —C (R ¹² ) ═ (C ₁ -C ₁₂ ) alkyl optionally substituted with a substituent selected from the group consisting of NOR ¹¹ ).
(2) ^{A 2} is, D1-6, D1-7, D1-15~D1-17, D1-25~D1-27 , D1-39, D1-40, D1-42, D1-44, D1-45 D1-47, D1-69, D1-73, D1-77, D1-78, D1-80, D1-81, D1-86, D1-87, D1-90 or D1-93, and p1, When p2, p3, p4 or p5 represents an integer of 1 or more,
X ¹ is a halogen atom, cyano, nitro, azide, —SCN, —SF ₅ , C ₁ -C ₁₂ alkyl, (C ₁ -C ₁₂ ) alkyl optionally substituted with R ⁵ , C ₃ -C ₁₂ cyclo. alkyl, optionally substituted with ^{R 5} _(C 3 ~C _{12) cycloalkyl,} C 2 _{-C 12} alkenyl, optionally substituted with ^{R 5} _(C 2 ~C _{12) alkenyl,} C 3 _{-C 12} cycloalkyl alkenyl, optionally substituted with ^{R 5} _(C 3 ~C _{12) cycloalkenyl,} C 2 _{-C 12} alkynyl, optionally substituted with ^{R 5} _(C 2 ~C _{12) alkynyl,} C 3 _{-C 12} allenyl _{^{, -OH, -OR 6, -SH,}} -S (O) r R 6, -S (= NR 8b) R 6a, -S (O) (= NR 8b) R 6a, -N (R 8a) R ^{8, -C (O) R 7} , -C (O) ^{H, -C (O) OR 6a} , -C (O) SR 6a, -C (S) OR 6a, -C (S) SR 6a, -C (O) N (R 8a) R 8, -C ( ^{S) N (R 8a) R} 8, -C (O) N (R 8a) N (R 8a) R 8, -C (O) N (R 8a) OR 6, -C (O) C (O) OR ^6a , -C (R ⁷ ) = NOH, -C (R ⁷ ) = NOR ⁶ , -C (R ⁷ ) = NN (R ^8a ) R ⁸ , -C (= NOR ⁶ ) N (R ^8a ) R ^{8, -C (= NR 8b)} OR 6a, -C (= NR 8b) SR 6a, -C (= NR 8b) N (R 8a) R 8, -S (O) 2 OR 6, -S (O ) ₂ N (R ^8a ) R ⁸ , -ON (R ^8a ) R ⁸ , -N (R ^8a ) OR ⁶ , -Si (R ^9a ) (R ^9b ) R ⁹ , -P (O) (OR ¹⁰ ) _2, -P (S ^(OR ₁₀₎ 2, -P _(phenyl) 2, -P (O) _{(phenyl) 2,} phenyl, ^naphthyl, (Z ₂₎ phenyl substituted with ^_q2, (Z ₂₎ is substituted with _q2 naphthyl or D2 -1 to D2-102, and when p1, p2, p4 or p5 represents an integer of 2 or more, each X ¹ may be the same as or different from each other, and two X ¹ Are adjacent to each other, two adjacent X ¹ 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} -, - CH 2 CH 2 CH 2 CH 2 -, - CH 2 CH 2 CH 2 O -, - CH 2 CH 2 OCH 2 -, - CH 2 OCH 2 O -, - OCH ₂ CH ₂ O—, —CH ₂ CH ₂ CH ₂ By forming S— or —OCH ₂ CH ₂ S—, a 5-membered ring or a 6-membered ring may be formed together with the carbon atom to which each X ¹ is bonded. At this time, each carbon atom forming the ring The hydrogen atom bonded to may be optionally substituted by X ² ,
X ^1a is a hydrogen atom, a halogen atom, cyano, nitro, azide, —SCN, —SF ₅ , C _{1 to} C ₁₂ alkyl, (C _{1 to} C ₁₂ ) alkyl optionally substituted with R ^5a , C ₃ to C ₁₂ ^cycloalkyl, optionally substituted with ^{R 5a} _(C 3 ~C _{12) cycloalkyl,} substituted C 2 _{-C 12} ^alkenyl, optionally with ^{R 5a} _(C 2 ~C _{12) alkenyl, C} 3 ~ C ₁₂ ^{cycloalkenyl,} optionally substituted with ^{R 5a} _(C 3 ~C _{12) cycloalkenyl,} C 2 _{-C 12} ^alkynyl, optionally substituted with ^{R 5a} _(C 2 ~C _{12) alkynyl, C} 3 ~ C _{12 ^{allenyl, -OH, -OR 6, -S (}} O) r R 6, -S (= NR 8b) R 6a, -S (O) (= NR 8b) R 6a, -N (R 8a) R ^8, -C (O) R ^{, -C (O) OR 6a,} -C (O) SR 6a, -C (S) OR 6a, -C (S) SR 6a, -C (O) N (R 8a) R 8, -C (S ) N (R ^8a ) R ⁸ , —C (O) N (R ^8a ) N (R ^8a ) R ⁸ , —C (O) N (R ^8a ) OR ⁶ , —C (O) C (O) OR ^{6a, -C (R 7) =} NOH, -C (R 7) = NOR 6, -C (R 7) = NN (R 8a) R 8, -C (= NOR 6) N (R 8a) R 8 ^{, -C (= NR 8b) OR} 6a, -C (= NR 8b) SR 6a, -C (= NR 8b) N (R 8a) R 8, -S (O) 2 N (R 8a) R 8, ^{-Si (R 9a) (R 9b} ) R 9, -P (O) (OR 10) 2, -P (S) (OR 10) 2, -P ( _phenyl) 2, -P _(O) (phenyl) _2, Fe Le, ^naphthyl, (Z ₂₎ phenyl substituted with ^_q2, represents a (Z ₂₎ naphthyl or D2-1~D2-102 substituted with _q2, ^{further, if X 1} is present at the adjacent position to ^{X 1a} the, ^{X 1a} and ^{X 1} _{adjacent, -CH 2 CH 2 O -,} - CH 2 CH 2 CH 2 CH 2 -, - CH = CHCH = CH -, - N = CHCH = CH -, - CH = By forming N—CH═CH—, —CH═CH—N═CH— or —CH═CH—CH═N—, a 5- or 6-membered ring with the atoms to which each of X ^1a and X ¹ is bonded is formed. At this time, the hydrogen atom bonded to each carbon atom forming the ring may be optionally substituted with a halogen atom, a C ₁ -C ₆ alkyl group or a C ₁ -C ₆ haloalkyl group. (provided that one or more of ^{X 1} or ^{X 1a} is S ^_(O) r ^{R 11,} from ^{-S (= NR 13b) R 11a} , -S (O) (= NR 13b) R 11a, -C (R 12) = NOH and ^-C (R 12) = ^{NOR 11} (C ₁ -C ₁₂ ) alkyl optionally substituted with a substituent selected from the group consisting of )
The parasite control composition according to claim 1. (1) ^{A 2} is D1-1, D1-2, D1-5~D1-17, D1-19, D1-20, D1-22~D1-26, D1-28, D1-29, D1-36~ D1-40, D1-42, D1-43, D1-46, D1-48, D1-52 to D1-57, D1-59 to D1-63, D1-67 to D1-70, D1-74, D1- 80-D1-87, D1-94-D1-96, D1-98, D1-99 or D1-103-D1-105, and p1, p2, p3, p4, p5, p6 or p8 is 1 or more It represents an integer, further if a carbon atom on a ² which binds to pyrazole 4-position represented by the carbon atom and the formula (B) on the a ² binding of X ¹ adjacent,
(1-1) X ¹ forms a methylene chain together with R ³ to form a 5-membered ring together with the carbon atom to which X ¹ is bonded, the carbon atom to which R ³ is bonded and the carbon atom to which A ² is bonded. In this case, the methylene chain may contain an oxygen atom, a sulfur atom or a nitrogen atom, and further contains a halogen atom, a cyano group, a nitro group, a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ haloalkyl group, C _{1 to} C ₆ alkoxy group, C _{1 to} C ₆ haloalkoxy group, C _{1 to} C ₆ alkylthio group, C _{1 to} C ₆ haloalkylthio group, —NH ₂ group, C _{1 to} C ₆ alkylamino group, di (C ₁ -C ₆₎ alkylamino group, phenyl, ^naphthyl, (Z ₂₎ phenyl substituted with _^q2, (Z _{2) q2} naphthyl or substituted with D2-1～D2-102, oxo group, thioxo group, an imino Group, Optionally substituted by a C ₁ -C ₆ alkylimino group or a C ₁ -C ₆ alkoxyimino group,
(1-2) X ¹ together with R ³ forms a C ₂ -C ₄ alkylene chain or a C ₂ -C ₄ alkenylene chain, whereby the carbon atom to which X ¹ is bonded and the carbon to which R ³ is bonded A 6- to 8-membered ring is formed together with the atom and the carbon atom to which A ² is bonded. At this time, the alkylene chain or alkenylene chain may contain an oxygen atom or a sulfur atom, and further contains a halogen atom, a cyano group, a nitro group, C _1. -C ₆ alkyl _group, C 1 -C ₆ haloalkyl _group, C 1 -C ₆ alkoxy _group, C 1 -C ₆ haloalkoxy _group, C 1 -C ₆ alkylthio _group, C 1 -C ₆ haloalkylthio group, -NH ₂ groups, C ₁ -C ₆ alkylamino group, di (C ₁ -C ₆ ) alkylamino group, phenyl, naphthyl, phenyl substituted with (Z ² ) _q ² , naphthyl substituted with (Z ² ) _q ² The D2-1～D2-102, oxo group, thioxo group, an imino _group, may be arbitrarily substituted with C 1 -C ₆ alkylimino or _C 1 -C ₆ alkoxyimino group,
Furthermore, when p1, p2, p4, p5, p6 or p8 represents an integer of 2 or more, the remaining X ¹ is a halogen atom, cyano, nitro, azide, —SCN, —SF ₅ , C ₁ -C ₁₂ alkyl. , optionally substituted with ^{R 5} _(C 1 ~C _{12) alkyl,} C 3 _{-C 12} cycloalkyl, optionally substituted with ^{R 5} _(C 3 ~C _{12) cycloalkyl,} C 2 _{-C 12} alkenyl , optionally substituted with ^{R 5} _(C 2 ~C _{12) alkenyl,} C 3 _{-C 12} cycloalkenyl, optionally substituted with ^{R 5} _(C 3 ~C _{12) cycloalkenyl,} C 2 _{-C 12} alkynyl , R ⁵ optionally substituted (C ₂ -C ₁₂ ) alkynyl, C ₃ -C ₁₂ allenyl, —OH, —OR ⁶ , —SH, —S (O) _r R ⁶ , —S (═NR ^8b ) ^R 6a, -S (O) ^{= NR 8b) R 6a, -N} (R 8a) R 8, -C (O) R 7, -C (O) OH, -C (O) OR 6a, -C (O) SR 6a, -C ( ^{S) OR 6a, -C (S} ) SR 6a, -C (O) N (R 8a) R 8, -C (S) N (R 8a) R 8, -C (O) N (R 8a) N ^{(R 8a) R 8, -C} (O) N (R 8a) OR 6, -C (O) C (O) OR 6a, -C (R 7) = NOH, -C (R 7) = NOR 6 ^{, -C (R 7) = NN} (R 8a) R 8, -C (= NOR 6) N (R 8a) R 8, -C (= NR 8b) OR 6a, -C (= NR 8b) SR 6a _{^{, -C (= NR 8b) N}} (R 8a) R 8, -S (O) 2 OR 6, -S (O) 2 N (R 8a) R 8, -ON (R 8a) R 8, -N ^(R 8a) OR ^{6 -Si (R 9a) (R 9b} ) R 9, -P (O) (OR 10) 2, -P (S) (OR 10) 2, -P ( _phenyl) 2, -P _(O) (phenyl) _2, phenyl, ^naphthyl, (Z ₂₎ phenyl substituted with ^_q2, (Z _{2) q2} represents naphthyl or D2-1~D2-102 substituted with, p1, p4, p5, p6 or p8 is 3 or more Each X ¹ may be the same as or different from each other, and when two X ¹ are adjacent to each other, the two adjacent X ¹ 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 —, —CH ₂ CH ₂ CH ₂ CH _{2 -, - CH 2 CH 2 CH} 2 O -, - CH 2 CH 2 OCH _The carbon to which each X ¹ is bonded by forming _2- , —CH ₂ OCH ₂ O—, —OCH ₂ CH ₂ O—, —CH ₂ CH ₂ CH ₂ S— or —OCH ₂ CH ₂ S—. A 5-membered ring or a 6-membered ring may be formed together with the atoms, and at this time, a hydrogen atom bonded to each carbon atom forming the ring may be optionally substituted by X ² ,
(2) ^{A 2} is D1-6, D1-15, D1-25, D1-27, D1-40, D1-44, D1-47, D1-50, D1-73, the D1-86 or D1-93 When representing
X ^1a is, by together with ^{R 3} to form a _C 2 -C ₄ alkylene chain or _C 2 -C ₄ alkenylene ^chain, a carbon atom and ^{A 2} nitrogen atoms and ^{R 3 which X 1a} is attached is bound Forms a 6-8 membered ring with the carbon atom to which is bonded, and at this time, the alkylene chain or alkenylene chain may contain 1 to 3 oxygen atoms, sulfur atoms or nitrogen atoms, and a halogen atom, cyano group, nitro group C ₁ -C ₆ alkyl group, C ₁ -C ₆ haloalkyl group, C ₁ -C ₆ alkoxy group, C ₁ -C ₆ haloalkoxy group, C ₁ -C ₆ alkylthio group, C ₁ -C ₆ haloalkylthio group , -NH _{2 group,} C 1 -C ₆ alkylamino group, di _(C 1 ~C ₆₎ alkylamino group, phenyl, ^naphthyl, (Z ₂₎ phenyl substituted with ^_q2, is substituted with (Z _{2) q2} Naphthyl or D2-1～D2-102, oxo group, thioxo group, an imino _group, may be arbitrarily substituted with C 1 -C ₆ alkylimino or _C 1 -C ₆ alkoxyimino group,
X ¹ is a halogen atom, cyano, nitro, azide, —SCN, —SF ₅ , C ₁ -C ₁₂ alkyl, (C ₁ -C ₁₂ ) alkyl optionally substituted with R ⁵ , C ₃ -C ₁₂ cyclo. alkyl, optionally substituted with ^{R 5} _(C 3 ~C _{12) cycloalkyl,} C 2 _{-C 12} alkenyl, optionally substituted with ^{R 5} _(C 2 ~C _{12) alkenyl,} C 3 _{-C 12} cycloalkyl alkenyl, optionally substituted with ^{R 5} _(C 3 ~C _{12) cycloalkenyl,} C 2 _{-C 12} alkynyl, optionally substituted with ^{R 5} _(C 2 ~C _{12) alkynyl,} C 3 _{-C 12} allenyl _{^{, -OH, -OR 6, -SH,}} -S (O) r R 6, -S (= NR 8b) R 6a, -S (O) (= NR 8b) R 6a, -N (R 8a) R ^{8, -C (O) R 7} , -C (O) ^{H, -C (O) OR 6a} , -C (O) SR 6a, -C (S) OR 6a, -C (S) SR 6a, -C (O) N (R 8a) R 8, -C ( ^{S) N (R 8a) R} 8, -C (O) N (R 8a) N (R 8a) R 8, -C (O) N (R 8a) OR 6, -C (O) C (O) OR ^6a , -C (R ⁷ ) = NOH, -C (R ⁷ ) = NOR ⁶ , -C (R ⁷ ) = NN (R ^8a ) R ⁸ , -C (= NOR ⁶ ) N (R ^8a ) R ^{8, -C (= NR 8b)} OR 6a, -C (= NR 8b) SR 6a, -C (= NR 8b) N (R 8a) R 8, -S (O) 2 OR 6, -S (O ) ₂ N (R ^8a ) R ⁸ , -ON (R ^8a ) R ⁸ , -N (R ^8a ) OR ⁶ , -Si (R ^9a ) (R ^9b ) R ⁹ , -P (O) (OR ¹⁰ ) _2, -P (S ^(OR ₁₀₎ 2, -P _(phenyl) 2, -P (O) _{(phenyl) 2,} phenyl, ^naphthyl, (Z ₂₎ phenyl substituted with ^_q2, (Z ₂₎ is substituted with _q2 naphthyl or D2 -1 to D2-102, and when p1, p2, p4, p5, p6 or p8 represents an integer of 2 or more, each X ¹ may be the same as or different from each other; When two X ¹ are adjacent to each other, the two adjacent X ¹ 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 -, - CH 2 CH 2 CH 2 CH 2 -, - CH 2 CH 2 CH 2 O -, - CH 2 CH 2 OCH 2 -, - CH 2 OCH 2 O _{-, - OCH 2 CH 2 O} -, - CH 2 C By forming H ₂ CH ₂ S— or —OCH ₂ CH ₂ S—, a 5-membered ring or a 6-membered ring may be formed together with the carbon atom to which each X ¹ is bonded. The hydrogen atom bonded to each carbon atom may be optionally replaced by X ² ;
(3) ^{A 2 is, (Z} ₁₎ phenyl or substituted with _q ^(Z ₁₎ represents naphthyl substituted with _q, and q represents an integer of 1 or more, the upper ^{A 2} which further bond ^{Z 1} And the carbon atom on A ² bonded to the 4-position of pyrazole of formula (B) are adjacent to each other, Z ¹ together with R ³ is a C _{2 to} C ₄ alkylene chain or C _{2 to} C By forming a _4- alkenylene chain, a 6-8 membered ring is formed together with the carbon atom to which Z ¹ is bonded, the carbon atom to which R ³ is bonded, and the carbon atom to which A ² is bonded. At this time, the alkylene chain or the alkenylene chain is It may contain an oxygen atom or a sulfur atom, and a halogen atom, a cyano group, a nitro _group, C 1 -C ₆ alkyl _group, C 1 -C ₆ haloalkyl _group, C 1 -C ₆ alkoxy _group, C 1 -C ₆ haloalkoxy _group, C 1 _{~C 6} A Kiruchio _group, C 1 -C ₆ haloalkylthio group, -NH _{2 group,} C 1 -C ₆ alkylamino group, di _(C 1 ~C ₆₎ alkylamino group, phenyl, ^naphthyl, substituted with (Z _{2) q2} Optionally substituted by phenyl, (Z ² ) _q2 substituted naphthyl or D2-1 to D2-102, oxo group, thioxo group, imino group, C ₁ -C ₆ alkylimino group or C ₁ -C ₆ alkoxyimino group May be replaced with
Further, when q represents an integer of 2 or more, the remaining Z ¹ is optionally substituted with a halogen atom, cyano, nitro, azide, —SCN, —SF ₅ , C ₁ -C ₁₂ alkyl, R ⁵ ( C ₁ -C ₁₂ ) alkyl, C ₃ -C ₁₂ cycloalkyl, optionally substituted with R ⁵ (C ₃ -C ₁₂ ) cycloalkyl, C ₂ -C ₁₂ alkenyl, optionally substituted with R ⁵ ( C ₂ -C _{12) alkenyl,} C 3 _{-C 12} cycloalkenyl, substituted optionally substituted with ^{R 5} _(C 3 ~C _{12) cycloalkenyl,} C 2 _{-C 12} alkynyl, optionally with ^{R 5} ( C ₂ -C _{12) alkynyl,} C 3 _{-C 12 ^{allenyl, -OH, -OR 6, -SH,}} -S (O) r R 6, -S (= NR 8b) R 6a, -S (O) ( = NR ^8b ) R ^6a , -N (R ^{8 a) R 8, -C (O} ) R 7, -C (O) OR 6a, -C (O) SR 6a, -C (S) OR 6a, -C (S) SR 6a, -C (O) ^{N (R 8a) R 8,} -C (S) N (R 8a) R 8, -C (O) N (R 8a) N (R 8a) R 8, -C (O) N (R 8a) OR ⁶ , -C (O) C (O) OR ^6a , -C (R ⁷ ) = NOH, -C (R ⁷ ) = NOR ⁶ , -C (R ⁷ ) = NN (R ^8a ) R ⁸ , -C ^{(= NOR 6a) N (R} 8a) R 8, -C (= NR 8b) OR 6a, -C (= NR 8b) SR 6a, -C (= NR 8b) N (R 8a) R 8, -S _{^{(O) 2 OR 6a, -S}} (O) 2 N (R 8a) R 8, -ON (R 8a) R 8, -N (R 8a) OR 6, -Si (R 9a) (R 9b) R ^9, -P (O _{^{(OR 10) 2, -P (}} S) (OR 10) 2, -P ( _phenyl) 2, P (O) _{(phenyl) 2,} phenyl, ^naphthyl, phenyl substituted with (Z _{2) q2,} (Z ² ) represents naphthyl substituted with _q2 or D2-1 to D2-102, and when q represents an integer of 3 or more, each Z ¹ may be the same as or different from each other; When two Z ¹ are adjacent to each other, the two adjacent Z ¹ 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 -, - CH 2 CH 2 N (X 1a) -, - CH 2 N (X 1a) CH 2 -, - 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 -, - CH 2 CH = CH -, - OCH = CH -, - SCH = CH -, - N (X 1a) ^{CH = CH -, - OCH =} N -, - SCH = N -, - N (X 1a) CH = N -, - N (X 1a) N = CH -, - OCH 2 CH = CH -, - N = By forming CHCH = CH-, -CH = NCH = CH-, -N = NCH = CH-, -CH = NN = CH-, -N = CHCH = N- or -N = CHN = CH- A 5-membered ring or a 6-membered ring may be formed together with the carbon atom to which each Z ¹ is bonded. At this time, the hydrogen atom bonded to each carbon atom forming the ring is optionally substituted with Z ² . The parasite control composition according to claim 1. R ¹ , R ³ and R ⁴ each independently represents a hydrogen atom, a halogen atom or C ₁ -C ₆ alkyl;
n1 and m1 represent the integer of 0, The parasite control composition of Claim 2. A ² is D1-1, D1-2, D1-5~D1-17, D1-19, D1-20, D1-22~D1-26, D1-28, D1-29, D1-36~D1-40 D1-42, D1-43, D1-46, D1-48, D1-52 to D1-57, D1-59 to D1-63, D1-67 to D1-70, D1-74, D1-80 to D1 -87, D1-94 to D1-96, D1-98, D1-99 or D1-103 to D1-105, and p1, p2, p3, p4, p5, p6 or p8 represents an integer of 1 or more. further if the carbon atom on a ² which binds to pyrazole 4-position represented by the carbon atom and formulas for a ² (B) to bond X ¹ is adjacent, X ¹ is taken together with R ³ to form a _C 2 -C ₄ alkylene chain or _C 2 -C ₄ alkenylene chain Te , To form a 6-8 membered ring with the carbon atom bonded carbon atoms and A ² binding carbon atoms and R ³ for coupling of X ^1, alkylene chain or alkenylene chain at this time, contain an oxygen atom or a sulfur atom Further, a halogen atom, a cyano group, a nitro group, a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ haloalkyl group, a C ₁ -C ₆ alkoxy group, a C ₁ -C ₆ haloalkoxy group, a C ₁ -C ₆ alkylthio group, C ₁ -C ₆ haloalkylthio group, —NH ₂ group, C ₁ -C ₆ alkylamino group, di (C ₁ -C ₆ ) alkylamino group, phenyl, naphthyl, substituted with (Z ² ) _q2 Phenyl, (Z ² ) _q2 substituted naphthyl or D2-1 to D2-102, oxo group, thioxo group, imino group, C ₁ -C ₆ alkylimino group or C ₁ -C ₆ alcohol Optionally substituted by a xyimino group,
Furthermore, when p1, p2, p4, p5, p6 or p8 represents an integer of 2 or more,
The remaining X ¹ is a halogen atom, cyano, nitro, azide, —SCN, —SF ₅ , C ₁ -C ₁₂ alkyl, (C ₁ -C ₁₂ ) alkyl optionally substituted with R ⁵ , C ₃ -C _C12 cycloalkyl, optionally substituted with ^{R 5} _(C 3 ~C _{12) cycloalkyl,} C 2 _{-C 12} alkenyl, optionally substituted with ^{R 5} _(C 2 ~C _{12) alkenyl,} C 3 -C ₁₂ cycloalkenyl, optionally substituted with ^{R 5} _(C 3 ~C _{12) cycloalkenyl,} C 2 _{-C 12} alkynyl, optionally substituted with ^{R 5} _(C 2 ~C _{12) alkynyl,} C 3 -C ₁₂ allenyl, —OH, —OR ⁶ , —SH, —S (O) _r R ⁶ , —S (═NR ^8b ) R ^6a , —S (O) (═NR ^8b ) R ^6a , —N (R ^{8a) ) R 8, -C (O)} R 7, -C ^{O) OH, -C (O)} OR 6a, -C (O) SR 6a, -C (S) OR 6a, -C (S) SR 6a, -C (O) N (R 8a) R 8, - ^{C (S) N (R 8a} ) R 8, -C (O) N (R 8a) N (R 8a) R 8, -C (O) N (R 8a) OR 6, -C (O) C ( O) OR ^6a , -C (R ⁷ ) = NOH, -C (R ⁷ ) = NOR ⁶ , -C (R ⁷ ) = NN (R ^8a ) R ⁸ , -C (= NOR ⁶ ) N (R ^{8a ) R 8, -C (= NR} 8b) OR 6a, -C (= NR 8b) SR 6a, -C (= NR 8b) N (R 8a) R 8, -S (O) 2 OR 6, -S _{^{(O) 2 N (R 8a}} ) R 8, -ON (R 8a) R 8, -N (R 8a) OR 6, -Si (R 9a) (R 9b) R 9, -P (O) (OR ¹⁰⁾ _2, - _{^{(S) (OR 10) 2}} , -P ( _phenyl) 2, -P (O) _{(phenyl) 2,} phenyl, ^naphthyl, phenyl substituted with (Z _{2) ^q2,} substituted with (Z _{2) q2} Naphthyl or D2-1 to D2-102,
X ^1a is a hydrogen atom, a halogen atom, cyano, nitro, azide, —SCN, —SF ₅ , C _{1 to} C ₁₂ alkyl, (C _{1 to} C ₁₂ ) alkyl optionally substituted with R ^5a , C ₃ to C ₁₂ ^cycloalkyl, optionally substituted with ^{R 5a} _(C 3 ~C _{12) cycloalkyl,} substituted C 2 _{-C 12} ^alkenyl, optionally with ^{R 5a} _(C 2 ~C _{12) alkenyl, C} 3 ~ C ₁₂ ^{cycloalkenyl,} optionally substituted with ^{R 5a} _(C 3 ~C _{12) cycloalkenyl,} C 2 _{-C 12} ^alkynyl, optionally substituted with ^{R 5a} _(C 2 ~C _{12) alkynyl, C} 3 ~ C _{12 ^{allenyl, -OH, -OR 6, -S (}} O) r R 6, -S (= NR 8b) R 6a, -S (O) (= NR 8b) R 6a, -N (R 8a) R ^8, -C (O) R ^{, -C (O) OR 6a,} -C (O) SR 6a, -C (S) OR 6a, -C (S) SR 6a, -C (O) N (R 8a) R 8, -C (S ) N (R ^8a ) R ⁸ , —C (O) N (R ^8a ) N (R ^8a ) R ⁸ , —C (O) N (R ^8a ) OR ⁶ , —C (O) C (O) OR ^{6a, -C (R 7) =} NOH, -C (R 7) = NOR 6, -C (R 7) = NN (R 8a) R 8, -C (= NOR 6) N (R 8a) R 8 ^{, -C (= NR 8b) OR} 6a, -C (= NR 8b) SR 6a, -C (= NR 8b) N (R 8a) R 8, -S (O) 2 N (R 8a) R 8, ^{-Si (R 9a) (R 9b} ) R 9, -P (O) (OR 10) 2, -P (S) (OR 10) 2, -P ( _phenyl) 2, -P _(O) (phenyl) _2, Fe Le, ^naphthyl, (Z ₂₎ phenyl substituted with _^q2, (Z _{2) q2} claim 3 parasite control composition according representing a naphthyl or D2-1~D2-102 substituted with. A ¹ represents -CR ¹
R ¹ and R ⁴ each independently represent a hydrogen atom, a halogen atom or C ₁ -C ₆ alkyl;
B represents a ring represented by any one of B-1 to B-6,


A ³ represents —O—, —S (O) _r1 —, —C (X ^1b ) X ^1c —,
X ^1b and X ^1c are each independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ haloalkyl group, a C ₁ -C ₆ alkoxy group, a C _1- C ₆ haloalkoxy group, C ₁ -C ₆ alkylthio group, C ₁ -C ₆ haloalkylthio group, —NH ₂ group, C ₁ -C ₆ alkylamino group, di (C ₁ -C ₆ ) alkylamino group, phenyl , ^naphthyl, (Z ₂₎ phenyl substituted with _^q2, (Z _{2) q2} at or represents naphthyl or D2-1~D2-102 substituted, or ^{X 1b} and ^{X 1c} is an oxo group together, thioxo group, an imino _group, may form a C 1 -C ₆ alkylimino or _C 1 -C ₆ alkoxyimino group,
X ^1d and X ^1f are each independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ haloalkyl group, a C ₁ -C ₆ alkoxy group, a C _1- C ₆ haloalkoxy group, C ₁ -C ₆ alkylthio group, C ₁ -C ₆ haloalkylthio group, —NH ₂ group, C ₁ -C ₆ alkylamino group, di (C ₁ -C ₆ ) alkylamino group, phenyl , ^naphthyl, (Z ₂₎ phenyl substituted with ^_q2, (Z ₂₎ or represents naphthyl or D2-1~D2-102 substituted with _q2, or ^{X 1d} and ^{X 1f} is an oxo group together, thioxo group, an imino _group, may form a C 1 -C ₆ alkylimino or _C 1 -C ₆ alkoxyimino group,
n represents an integer of 1 to 2,
n1 represents an integer of 0;
The parasite control composition according to claim 5, wherein r and r1 each independently represents an integer of 0 to 2. X ^1b and X ^1c are each independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ haloalkyl group, a C ₁ -C ₆ alkoxy group, a C _1- C ₆ haloalkoxy group, C ₁ -C ₆ alkylthio group, C ₁ -C ₆ haloalkylthio group, —NH ₂ group, C ₁ -C ₆ alkylamino group, di (C ₁ -C ₆ ) alkylamino group ,
X ^1d and X ^1f are each independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ haloalkyl group, a C ₁ -C ₆ alkoxy group, a C _1- C ₆ haloalkoxy group, C ₁ -C ₆ alkylthio group, C ₁ -C ₆ haloalkylthio group, —NH ₂ group, C ₁ -C ₆ alkylamino group, di (C ₁ -C ₆ ) alkylamino group ,
X ¹ is halogen atom, cyano group, nitro group, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted with R ⁵ , C ₃ -C ₈ cycloalkyl, optionally with R ⁵ substituted _(C 3 ~C _{8) cycloalkyl,} C 2 -C ₆ alkenyl, optionally substituted with ^{R 5} _(C 2 ~C _{6) alkenyl,} C 3 -C ₈ cycloalkenyl, optionally by ^{R 5} substituted _(C 3 ~C _{8) cycloalkenyl,} C 2 -C ₆ alkynyl, optionally substituted with ^{R 5} _(C 2 ~C ₆₎ alkynyl, ^phenyl, phenyl substituted with (Z _{2) q2,} D2-32, D2-33, D2-34, D2-36, D2-37 or D2-38,
X ^1a represents a hydrogen _atom, C 1 -C ₆ alkyl, optionally substituted with ^{R 5a} _(C 1 ~C _{6) alkyl,} C 3 -C ₈ cycloalkyl, optionally substituted with ^{R 5a} _{(C 3} -C _{8) cycloalkyl,} C 2 -C ₆ alkenyl, optionally substituted with ^{R 5a} _(C 2 ~C _{6) alkenyl,} C 3 -C ₈ cycloalkenyl, optionally substituted with ^{R 5a} _{(C 3} -C _{8) cycloalkenyl,} optionally substituted with C 2 -C ₆ alkynyl, or ^{R 5a} _(C 2 ~C ₆₎ alkynyl,
R ⁵ and R ^5a are each independently a halogen atom, cyano, C ₃ -C ₈ cycloalkyl, —OH, —OR ^11, —SH, —S (O) _r R ¹¹ , —S (═NR ^13b ). R ^11a , —S (O) (═NR ^13b ) R ^11a , —N (R ^13a ) R ¹³ , —C (O) R ¹² , —C (O) OR ^11a , —C (O) N (R ^13a ) ) R ¹³ , -C (R ₁₂ ) = NOH or -C (R ₁₂ ) = NOR ₁₁
X ² represents a halogen atom, cyano, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, —OR ²⁵ or —S (O) _r R ²⁵ ,
Z ² represents a halogen atom, cyano, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, —OR ²⁵ or —S (O) _r R ²⁵ ,
R ¹¹ and R ^11a each independently represent C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl or C ₃ -C ₈ cycloalkyl,
R ¹² , R ¹³ , R ^13a and R ^13b are each independently a hydrogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl or C _3. It represents -C ₈ cycloalkyl,
R ²⁵ represents a hydrogen atom, C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
t1 and t4 each independently represents an integer of 0 to 2,
q2 represents an integer of 1 to 2,
The parasite control composition according to claim 6, wherein n represents an integer of 1. R ¹ and R ⁴ represent a hydrogen atom,
B represents a ring represented by any of B-1a, B-2a, B-2b, B-3a to B-5a,


X ¹ represents (C ₁ -C ₆ ) alkyl or D2-37 optionally substituted with R ⁵ ,
X ^1a represents a hydrogen atom or (C ₁ -C ₆ ) alkyl optionally substituted with R ^5a ,
X ^1b and X ^1c each independently represent a hydrogen atom or C ₁ -C ₆ alkyl,
R ⁵ represents —S (O) _r R ¹¹ ,
R ^5a represents a halogen atom, cyano, —OR ¹¹ or —S (O) _r R ¹¹ ,
R ¹¹ represents C ₁ -C ₆ alkyl,
The parasite control composition according to claim 7, wherein m1 and t1 represent 0. R ¹ and R ⁴ represent a hydrogen atom,
(1) A ² represents D1-14, D1-31, D1-34, D1-35, D1-52, D1-57 or D1-68, and p1, p3, p4 or p8 represents an integer of 1. If
X ¹ represents (C ₁ -C ₆ ) alkyl optionally substituted with R ⁵ ,
R ⁵ represents —S (O) _r R ¹¹ ,
R ¹¹ represents C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
r represents an integer of 0 to 2;
(2) if ^{A 2} is, to represent the D1-15 or D1-17, p2 represents an integer of 1,
X ¹ represents (C ₁ -C ₆ ) alkyl optionally substituted with R ⁵ ,
X ^1a _is, represent a C 1 -C ₆ alkyl or _C 1 -C ₆ haloalkyl, ^{or, when X 1} is present at the adjacent position to ^{X 1a} is, ^{X 1a} and ^{X 1} adjacent the -CH ₂ By forming CH ₂ O—, a 5-membered ring may be formed with the atom to which each of X ^1a and X ¹ is bonded,
R ⁵ represents —S (O) _r R ¹¹ ,
R ¹¹ represents C ₁ -C ₆ alkyl,
r represents an integer of 0 to 2;
(3) ^{A 2} is, D1-15, represents D1-16 or D1-17, if p2 represents an integer of 0,
X ^1a represents (C ₁ -C ₆ ) alkyl or —C (O) R ⁷ optionally substituted with R ^5a ,
R ^5a represents -S (O) _r R ¹¹ , -C (R ¹² ) = NOR ¹¹ , -S (= NR ^13b ) R ^11a or -S (O) (= NR ^13b ) R ^11a ,
R ⁷ represents (C ₁ -C ₆ ) alkyl optionally substituted with R ¹⁴ ;
R ¹¹ represents C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl or —C (O) R ¹⁶ ,
R ^11a , R ¹² , R ¹⁵ and R ¹⁶ each independently represent C ₁ -C ₆ alkyl;
R ^13b represents cyano,
R ¹⁴ represents -S (O) _r R ¹⁵ ;
The parasite control composition according to claim 4, wherein r represents an integer of 0 to 2.   The parasite control composition according to any one of claims 1 to 9, which is orally administered to an animal.   The parasite control composition according to any one of claims 1 to 9, which is parenterally administered to an animal.   The parasite control composition according to claim 11, wherein the parenteral administration method to animals is administration by injection or transdermal administration.   The parasite control composition according to any one of claims 1 to 12, wherein the animal is a mammal.   Mammals are rabbit, guinea pig, hamster, gerbil, mouse, rat, squirrel, monkey, dog, ferret, cat, yak, cow, buffalo, goat, sheep, antelope, deer, reindeer, boar, pig, camel, alpaca, llama It is a donkey, a horse, or a kangaroo, The parasite control composition of Claim 13.   The parasite control composition according to any one of claims 1 to 14, wherein the parasite is an ectoparasite invertebrate animal.   16. The parasite according to claim 15, wherein the animal ectoparasite invertebrate is a fly, ab, nukaka, buyu, mosquito, flea, lice, lice, mites, mites, mites, mites, mites, ticks, sand mites or tick mites. Control composition.   A method for controlling parasites comprising orally administering an effective amount of the composition for controlling parasites according to any one of claims 1 to 9 to animals.   A method for controlling parasites, wherein an effective amount of the composition for controlling parasites according to any one of claims 1 to 9 is administered parenterally to an animal.   The method for controlling parasites according to claim 18, wherein the parenteral administration method is administration by injection or transdermal administration.   The parasite control method according to any one of claims 17 to 19, wherein the animal is a mammal.   Mammals are rabbit, guinea pig, hamster, gerbil, mouse, rat, squirrel, monkey, dog, ferret, cat, yak, cow, buffalo, goat, sheep, antelope, deer, reindeer, boar, pig, camel, alpaca, llama The method for controlling a parasite according to claim 20, which is a donkey, a horse, or a kangaroo.   The parasite control method according to any one of claims 17 to 21, wherein the parasite is an ectoparasite invertebrate animal.   23. The parasite according to claim 22, wherein the animal ectoparasite invertebrate is a fly, ab, nukaka, buyu, mosquito, flea, lice, lice, mites, mites, mites, mites, mites, ticks, tick mites, or tick mites. Control method.