JP2013082699A - Pyrazole derivative and pest control agent - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a novel pest control agent, in particular, an insecticide or an acaricide.SOLUTION: The pyrazole derivative and the pest control agent are expressed by General Formula (1), wherein Arepresents -N(O)m2 or -CR, Rand Rrepresent respectively independently hydrogen atoms, halogen atoms, and C-Calkyls or the like, Rrepresents -C(O)N(R) R, -C(S) N(R)Ror the like, Rrepresents -C(R)=NOH, -C(R)=NORor the like, Rc represents hydrogen atom or the like, Rand Rrepresent respectively independently C-Calkyls or the like, and m1 and m2 represent respectively independently integers of 0 or 1.

Description

  The present invention relates to a novel pyrazole derivative and a salt thereof, and a pest control agent containing the compound as an active ingredient. The pest control agent in the present invention is the field of agriculture and horticulture or the field of livestock and hygiene (internal parasites / external parasites for domestic animals and pets, hygiene pests and unpleasant pests for domestic and commercial use) It means a pest control agent for harmful arthropods such as The agrochemical in the present invention means an insecticide / acaricide, nematicide, herbicide, fungicide, etc. in the field of agriculture and horticulture.

  Patent Documents 7 to 17 and Non-Patent Document 1 disclose pyrazol-4yl-amide and pyrazol-4yl-thioamide derivatives, but neither suggests nor discloses that they have insecticidal activity. On the other hand, Patent Documents 1 to 6 disclose that pyrazol-4yl-amide derivatives and pyrazol-4yl-thioamide derivatives are useful as insecticides, but no disclosure is made about the pyrazole compounds according to the present invention. It has not been.

International Publication No. 2011-045240 International Publication No. 2010/112177 International Publication No. 2010/034738 International Publication No. 2010/034737 International Publication No. 2009/149858 International Publication No. 2009/027393 International Publication No. 2009/013211 International Publication No. 2008/098798 International Publication No. 2008/034731 International Publication No. 2008/011131 International Publication No. 2007/093515 US Patent Application Publication No. 2007/191406 US Patent Application Publication No. 2007/191335 International Publication No. 2007/085567 International Publication No. 2004/099156 International Publication No. 2004/098518 German Patent Invention No. 2612155

Bioorganic and Medicinal Chemistry 2010, 18, p. 2785

  The development of pest control agents for the purpose of controlling various pests such as agricultural and horticultural pests, forest pests, and hygiene pests has progressed, and a wide variety of drugs have been put to practical use to date.

  However, due to the long-term use of such drugs, in recent years, pests have acquired drug resistance, making it difficult to control with existing insecticides and fungicides that have been used. In addition, some existing pest control agents are highly toxic, or some of them remain in the environment for a long time, and the problem of disturbing the ecosystem is becoming apparent. Under such circumstances, development of a novel pest control agent having not only high pest control activity but also low toxicity and low persistence is always expected.

  As a result of intensive research aimed at solving the above problems, the present inventors have found that the novel pyrazole derivative represented by the following general formula (1) according to the present invention has excellent pest control activity, particularly insecticide / killing. The present invention was completed by discovering that it is a very useful compound that exhibits mite activity and has almost no adverse effect on non-target organisms such as mammals, fish and beneficial insects.

  That is, the present invention relates to the following [1] to [9].

[1]
General formula (1):

Wherein, ^{A 1} is, -N _{(-O) m2} or represents -CR ^1,
R ¹ , R ³ and R ⁴ are each independently optionally substituted with a hydrogen atom, a halogen atom, cyano, nitro, —OH, —SH, —NH ₂ , C ₁ -C ₆ alkyl, R ^28a ( C ₁ -C ₆ ) alkyl, C ₃ -C ₈ cycloalkyl, optionally substituted with R ^28a (C ₃ -C ₈ ) cycloalkyl, C ₂ -C ₆ alkenyl, optionally substituted with R ^28a ( C ₂ -C _{6) alkenyl,} C 3 -C ₈ ^{cycloalkenyl,} substituted optionally substituted with ^{R 28a} _(C 3 ~C _{8) cycloalkenyl,} C 2 -C ₆ ^alkynyl, optionally with ^{R 28a} ( C ₂ -C _{6) alkynyl,} 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,} C 1 -C _{6 alkylcarbonyl,} C 3 -C _{8 cycloalkylcarbonyl,} C 1 -C _{6 haloalkylcarbonyl,} C 3 -C ₈ halocycloalkylcarbonyl, 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 alkyl Represents amino or di (C ₁ -C ₆ alkyl) amino;
R ² is a halogen atom, cyano, nitro, —OH, —SH, —NH ₂ , C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted with R ^28a , C ₃ -C _8. ^cycloalkyl, substituted optionally substituted with ^{R 28a} _(C 3 ~C _{8) cycloalkyl,} C 2 -C ₆ ^alkenyl, optionally with ^{R 28a} _(C 2 ~C _{6) alkenyl,} C 3 -C ₈ ^{cycloalkenyl,} optionally substituted with ^{R 28a} _(C 3 ~C _{8) cycloalkenyl,} C 2 -C ₆ ^alkynyl, which is optionally substituted with ^{R 28a} _(C 2 ~C _{6) alkynyl,} 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 ha B _{alkylsulfinyl,} C 1 -C _{6 haloalkylsulfonyl,} C 1 -C _{6 alkylcarbonyl,} C 3 -C _{8 cycloalkylcarbonyl,} C 1 -C _{6 haloalkylcarbonyl,} C 3 -C ₈ halocycloalkyl _{carbonyl, 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 or di _(C 1 -C ₆ Alkyl) amino, and when n represents an integer of 2 or more, each R ² may be the same as or different from each other,
R ^a represents —C (O) N (R ^b ) R ^c or —C (S) N (R ^b ) R ^c ,
R ^b is (C ₁ -C ₁₂ ) alkyl optionally substituted with R ^5a , -C (R ⁷ ) = NOH, -C (R ⁷ ) = NOR ⁶ , -C (= NOR ⁶ ) OR ^6a , ^{-C (= NOR 6) SR 6a} , -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, represents ^{-C (R 7) = NR 8b} , -N (R 8g) R 8 or ^{-N = C (R 7a) R} 7b,
R ^c is hydrogen _atom, 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, optionally substituted with ^{R 5} _(C 2 _{~C 12) ^{alkynyl, -OR 6c, -S (O)}} r2 R 6c, -C (O) R ^{7c, -C (O) OR 6a} , -C (O) SR 6a, -C (S) OR 6a, -C (S) SR 6a, -N (R 8a) R 8, -C (O) N ( ^{R 8a) R 8 -C (S} ) N (R 8a) R 8, -S (O) _{^{r2 N (R 8a) R 8}} , phenyl, or represents _(Z) phenyl substituted with _q, naphthyl, _(Z) naphthyl substituted with _q or D1-1～D1-94, or, ^{R c} is R together with ^b may form ═C (R ^8c ) R ^8d ,
R ⁵ is a halogen atom, cyano, nitro, C ₃ -C ₈ cycloalkyl, —OH, —OR ¹¹ , —SH, —S (O) _{r 2} R ¹¹ , —C (O) R ¹² , —C (O ) OR ^11a , -C (O) SR ^11a , -C (S) OR ^11a , -C (S) SR ^11a , -N (R ^13a ) R ¹³ , -C (O) N (R ^13a ) R ¹³ , _{^{-C (S) N (R 13a}} ) R 13, -S (O) r2 N (R 13a) R 13, -C (R 12) = NOH, -C (R 12) = NOR 11, phenyl, (Z ) phenyl substituted with _q, represents naphthyl, the naphthyl or D1-1~D1-94 substituted with _{(Z) q,}
R ^5a represents —C (R ¹² ) = NOH, —C (R ¹² ) = NOR ¹¹ or —C (O) N (R ¹³ ) R ^13f ,
R ⁶ , R ^6a and R ^6c are each independently C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted with R ¹⁴ , C ₃ -C ₈ cycloalkyl, optional with R ¹⁴ substituted in _(C 3 ~C _{8) cycloalkyl,} C 2 -C ₆ ^alkenyl, optionally substituted with ^{R 14} _(C 2 ~C _{6) alkenyl,} C 3 -C ₈ ^{cycloalkenyl,} optionally ^{R 14} (C ₃ -C ₈ ) cycloalkenyl, C ₂ -C ₆ alkynyl, (C ₂ -C ₆ ) alkynyl optionally substituted with R ¹⁴ , —S (O) _r R ¹¹ , —C ( ^{O) R 12, -C (O} ) OR 11, -C (O) SR 11, -C (S) OR 11, -C (S) SR 11, -C (O) N (R 13a) R 13 - ^{C (S) N (R 13a} ) R 13, -S (O) r2 N (R 13a ) R ¹³ , phenyl, (Z) _q- substituted phenyl, naphthyl, (Z) _q- substituted naphthyl or D1-1 to D1-94,
R ⁷ , R ^7a and R ^7c are each independently a hydrogen atom, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted with R ¹⁴ , C ₃ -C ₈ cycloalkyl, R optionally substituted with ¹⁴ _(C 3 ~C _{8) cycloalkyl,} C 2 -C ₆ ^alkenyl, optionally substituted with ^{R 14} _(C 2 ~C _{6) alkenyl,} C 3 -C ₈ cycloalkenyl, R optionally substituted with ¹⁴ _(C 3 ~C _{8) cycloalkenyl,} optionally substituted with C 2 -C _{6 ^{alkynyl, R 14 (C 2 ~C 6}} ) ^alkynyl, -OR ^11, -S (O) _{^{r R 11, -C (O)}} R 12, -C (O) OR 11, -C (O) SR 11, -C (S) OR 11, -C (S) SR 11, -C (O) N ^{(R 13a) R 13 -C (} S) N (R 13a) R 13, -S _{^{O) r2 N (R 13a)}} R 13, represents phenyl, _(Z) phenyl substituted with _q, naphthyl, naphthyl or substituted with _{(Z) q} D1-1～D1-94,
R ^7b is a hydrogen _atom, C 1 -C ₆ ^alkyl, optionally substituted with ^{R 14} _(C 1 ~C _{6) alkyl,} C 3 -C ₈ ^cycloalkyl, optionally substituted with ^{R 14} _{(C 3} -C _{8) cycloalkyl,} C 2 -C ₆ ^alkenyl, optionally substituted with ^{R 14} _(C 2 ~C _{6) alkenyl,} C 3 -C ₈ ^{cycloalkenyl,} optionally substituted with ^{R 14} _{(C 3} -C _{8) cycloalkenyl,} C 2 -C ₆ ^alkynyl, optionally substituted with ^{R 14} _(C 2 ~C ₆₎ alkynyl, phenyl, phenyl substituted with _{(Z) q,} naphthyl, with _{(Z) q} Represents substituted naphthyl or D1-1 to D1-94, or R ^7b and R ^7a together form a C _{3 to} C ₆ alkylene chain or a C _{3 to} C ₆ alkenylene chain to form R ^7b and ^{R 7} There may form a 4 to 7 membered ring with the carbon atoms to which they are attached alkylene chain or alkenylene chain this time, an oxygen atom, it may contain one to three sulfur atom or a nitrogen atom, and a halogen atom, a cyano group , A nitro group, a C ₁ -C ₆ alkyl group, a (C ₁ -C ₆ ) alkyl optionally substituted with R ¹⁴ , optionally —OR ¹⁵ , —S (O) _r R ¹⁵ , an oxo group or a thioxo group May be replaced,
R ⁸ and R ^8a are each independently a hydrogen atom, cyano, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted with R ¹⁴ , C ₃ -C ₈ cycloalkyl, R ^14. optionally substituted _(C 3 ~C _{8) cycloalkyl,} C 2 -C ₆ ^alkenyl, optionally substituted with ^{R 14} _(C 2 ~C _{6) alkenyl,} C 3 -C ₈ cycloalkenyl ^{in, R 14} (C ₃ -C ₈ ) cycloalkenyl, C ₂ -C ₆ alkynyl, (C ₂ -C ₆ ) alkynyl optionally substituted with R ¹⁴ , —OR ¹¹ , —S (O) _r R ¹¹ , —C (O) R ¹² , —C (O) OR ¹¹ , —C (O) SR ¹¹ , —C (S) OR ¹¹ , —C (S) SR ¹¹ , —C (O) N ( ^{R 13a) R 13, -C (} S) N (R 13a) R 13, -S _{^{O) r2 N (R 13a)}} R 13, phenyl, or represents _(Z) phenyl substituted with _q, naphthyl, naphthyl or substituted with _{(Z) q} D1-1～D1-94, or, ^{R 8} May form a C ₂ -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, in which case the alkylene chain May contain one oxygen, sulfur or nitrogen atom, and is optionally substituted with a halogen atom, cyano, C ₁ -C ₆ alkyl, R ¹⁴ (C ₁ -C ₆ ) alkyl, phenyl, (Z ) Optionally substituted by a phenyl, oxo or thioxo group substituted by _q , or R ⁸ together with R ^8a may form ═C (R ^8c ) R ^8d ,
R ^8b is hydrogen, _cyano, C 1 -C ₆ ^alkyl, optionally substituted with ^{R 14} _(C 1 ~C _{6) alkyl,} substituted C 3 -C ₈ ^cycloalkyl, optionally with ^{R 14} ( C ₃ -C _{8) cycloalkyl,} C 2 -C ₆ ^alkenyl, optionally substituted with ^{R 14} _(C 2 ~C _{6) alkenyl,} C 3 -C ₈ ^{cycloalkenyl,} optionally substituted with ^{R 14} ( C ₃ -C _{8) cycloalkenyl,} C 2 -C ₆ ^alkynyl, optionally substituted with ^{R 14} _(C 2 ~C _{6) ^{alkynyl, -OR 11, -S (O)}} r R 11, -C (O ^{) R 12, -C (O)} OR 11, -C (O) SR 11, -C (S) OR 11, -C (S) SR 11, -C (O) N (R 13a) R 13, - ^{C (S) N (R 13a} ) R 13, -S (O) r N (R 13 ) ^{R 13,} represents phenyl, _(Z) phenyl substituted with _q, naphthyl, naphthyl or substituted with _{(Z) q} D1-1～D1-94,
R ^8g represents —C (O) R ^12a , —C (O) N (R ^13f ) R ¹³ , —C (S) N (R ^13f ) R ¹³ or —S (O) _r R ¹¹ ,
R ^8c represents a hydrogen atom, —OR ¹¹ , —S (O) _r R ¹¹ , —N (R ^13a ) R ¹³ or —N (R ^13c ) N (R ^13a ) R ¹³ ;
R ^8d is a hydrogen atom, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted with R ¹⁴ , —OR ^11b , —S (O) _r R ^11b or —N (R ^13e ). R ^13d represents or, alternatively, R ^8d and R ^8c together form a C ₄ -C ₆ alkylene chain or a C ₄ -C ₆ alkenylene chain, so that together with the carbon atom to which R ^8d and R ^8c are attached A 5- to 7-membered ring may be formed, and 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 ) alkyl optionally substituted with R ¹⁴ , C ₃ -C ₈ cycloalkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, -OR ¹⁵ ,- S _{(O) r} ^15, phenyl, _(Z) phenyl substituted with _q, naphthyl, _(Z) naphthyl substituted with _q, D1-1～D1-94, may be optionally substituted by oxo or thioxo group,
R ¹¹ , R ^11a and R ^11b are each independently C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted with R ^14a , C ₂ -C ₆ alkenyl, optionally with R ^14a substituted _(C 2 ~C _{6) alkenyl,} C 3 -C ₈ ^{cycloalkenyl,} optionally substituted with ^{R 14a} _(C 3 ~C _{8) cycloalkenyl,} C 2 -C ₆ ^alkynyl, optionally with ^{R 14a} substituted _(C 2 ~C _{6) alkynyl,} C 3 -C ₈ ^cycloalkyl, optionally substituted with ^{R 14a} _(C 3 ~C ₈₎ cycloalkyl, phenyl, phenyl substituted with _{(Z) q,} Naphthyl, (Z) naphthyl substituted with _q or D1-1 to D1-94,
R ¹² is a hydrogen _atom, C 1 -C ₆ ^alkyl, optionally substituted with ^{R 14a} _(C 1 ~C _{6) alkyl,} C 2 -C ₆ ^alkenyl, optionally substituted with ^{R 14a} _(C 2 ~ C _{6) alkenyl,} C 3 -C ₈ ^{cycloalkenyl,} optionally substituted with ^{R 14a} _(C 3 ~C _{8) cycloalkenyl,} optionally substituted with C 2 -C ₆ ^{alkynyl, R 14a} _(C 2 ~ C ₆ ) alkynyl, C ₃ -C ₈ cycloalkyl, (C ₃ -C ₈ ) cycloalkyl optionally substituted with R ^14a , phenyl, (Z) _q substituted phenyl, naphthyl, (Z) _q Represents substituted naphthyl or D1-1 to D1-94;
R ¹³ , R ^13c , R ^13d and R ^13e each independently represent a hydrogen atom or R ^11a ,
R ^12a represents (C ₁ -C ₆ ) alkyl optionally substituted with R ^14a , or R ^12a together with R ⁸ is a C ₂ -C ₆ alkylene chain or C ₂ -C ₆ By forming an alkenylene chain, a 4- to 8-membered ring may be formed together with the carbon atom to which R ^12a is bonded and the nitrogen atom to which R ⁸ is bonded. At this time, the alkylene chain or alkenylene chain is an oxygen atom, a sulfur atom Alternatively, it may contain 1 or 2 nitrogen atoms and is a halogen atom, cyano, nitro, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted with R ^14a , —OH, —OR ¹⁵ , —SH, —S (O) _r R ¹⁵ , an oxo group or a thioxo group,
R ^13a represents a hydrogen atom, R ^11a , —C (O) OR ^15a or —C (O) R ¹⁶ , or R ^13a together with R ¹³ represents a C _{2 to} C ₇ alkylene chain. Forming a 3- to 8-membered ring together with the nitrogen atom to which R ^13a and R ¹³ are bonded, wherein the alkylene chain may contain one oxygen, sulfur or nitrogen atom, and A halogen atom, cyano, nitro, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted with R ^14a , —OH, —OR ¹⁵ , —SH, —S (O) _r R ¹⁵ , Optionally substituted by an oxo or thioxo group,
R ^13f represents (C ₁ -C ₆ ) alkyl optionally substituted with R ^14a ,
R ¹⁴ and R ^14a are each independently a halogen atom, cyano, nitro, C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ halocycloalkyl, —OH, —OR ¹⁵ , —SH, —S (O). _{^{r R 15, -N (R 17a}} ) R 17, -C (O) OH, -C (O) OR 15a, -CHO, -C (O) R 16, -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) r2 N (R 17a) R ¹⁷ , phenyl, phenyl substituted with (Z) _q , naphthyl, naphthyl substituted with (Z) _q or D1-1 to D1-94,
R ¹⁵ , R ^15a and R ¹⁶ are each independently C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₃ -C ₈ cycloalkyl or It represents C ₃ -C ₈ cycloalkenyl,
R ¹⁷ and R ^17a 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, C ₃ -C ₈ cycloalkyl or It represents C ₃ -C ₈ cycloalkenyl,
D1-1 to D1-94 each represent a ring represented by the following structural formula;

X ¹ is a halogen atom, cyano, nitro, —OH, —SH, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted with R ²⁸ , C ₂ -C ₆ alkenyl, R ^28. (C ₂ -C ₆ ) alkenyl optionally substituted with, C ₃ -C ₈ cycloalkenyl, (C ₃ -C ₈ ) cycloalkenyl optionally substituted with R ²⁸ , C ₂ -C ₆ alkynyl, R ²⁸ optionally substituted in _(C 2 ~C _{6) alkynyl,} C 3 -C ₈ ^cycloalkyl, optionally substituted with ^{R 28} _(C 3 ~C ₈₎ ^cycloalkyl, -OR ^25, -S (O) _{^{r R 25, -C (O)}} OH, -C (O) OR 25a, -C (O) R 26, -C (O) N (R 27a) R 27, -C (S) N (R 27a) R ²⁷ , —N (R ^27a ) R ²⁷ , —C (= NOR ^{25 _{) R 26, -S (O)}} 2 N (R 27a) R 27, ^phenyl, (Z ₂₎ phenyl substituted with _q2, ^naphthyl, (Z ₂₎ is substituted with _q2 naphthyl or D2-1~D2- 41, and when g1, g2, or g4 represents an integer of 2 or more, each X ¹ may be the same as or different from each other, and when two X ¹ are adjacent, adjacent to each other The two X ¹ groups represented by —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 it may be each of X ¹ to form a 5- or 6-membered ring with the carbon atoms to which they are attached hydrogen atoms bonded to the time each of the carbon atoms forming the ring, 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 alkylsulfinyl group or a _C 1 -C ₆ alkylsulfonyl group Optionally substituted by
X ^1a represents a hydrogen atom, cyano, _-OH, optionally substituted with C 1 -C ₆ ^alkyl, optionally substituted with ^{R 28} _(C 1 ~C _{6) alkyl,} C 2 -C ₆ ^{alkenyl, R 28} and _(C 2 ~C _{6) alkenyl,} C 3 -C ₈ ^{cycloalkenyl,} substituted optionally substituted with ^{R 28} _(C 3 ~C _{8) cycloalkenyl,} optionally with C 2 -C ₆ ^{alkynyl, R 28} (C ₂ -C ₆ ) alkynyl, C ₃ -C ₈ cycloalkyl, (C ₃ -C ₈ ) cycloalkyl optionally substituted with R ²⁸ , —OR ²⁵ , —S (O) _r R ²⁵ , — C (O) OH, —C (O) OR ^25a , —C (O) R ²⁶ , —C (O) N (R ^27a ) R ²⁷ , —C (S) N (R ^27a ) R ²⁷ , —N ^{(R 27a) R 27, -C} (= NOR 25) R 26, -S ( _{^{) 2 N (R 27a) R}} 27, represents ^phenyl, (Z ₂₎ phenyl substituted with _q2, ^naphthyl, (Z ₂₎ naphthyl or D2-1~D2-41 substituted with _q2,
X ^1b is a halogen atom, cyano, nitro, —OH, —SH, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted with R ²⁸ , C ₂ -C ₆ alkenyl, R ^28. (C ₂ -C ₆ ) alkenyl optionally substituted with, C ₃ -C ₈ cycloalkenyl, (C ₃ -C ₈ ) cycloalkenyl optionally substituted with R ²⁸ , C ₂ -C ₆ alkynyl, R ²⁸ optionally substituted in _(C 2 ~C _{6) alkynyl,} C 3 -C ₈ ^cycloalkyl, optionally substituted with ^{R 28} _(C 3 ~C ₈₎ ^cycloalkyl, -OR ^25, -S (O) _{^{r R 25, -C (O)}} OH, -C (O) OR 25a, -C (O) R 26, -C (O) N (R 27a) R 27, -C (S) N (R 27a) R ²⁷ , —N (R ^27a ) R ²⁷ , —C (= NOR ^{2 _{5) R 26, -S (O}} ) 2 N (R 27a) R 27, ^phenyl, (Z ₂₎ phenyl substituted with _q2, ^naphthyl, (Z ₂₎ is substituted with _q2 naphthyl or D2-1~D2 -41, and when f1, f2, f4, f5, f6, f7, f8 or f9 represents an integer of 2 or more, each X ^1b may be the same as or different from each other; When two X ^1b are substituted on the same carbon, the two X ^1b together are oxo, thioxo, imino, C ₁ -C ₆ alkylimino, C ₁ -C ₆ alkoxyimino or C _1- C ₆ alkylidene may be formed,
Z is a halogen atom, cyano, nitro, —OH, —SH, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted with R ²⁸ , C ₂ -C ₆ alkenyl, R ²⁸ optionally substituted _(C 2 ~C _{6) alkenyl,} C 3 -C ₈ ^{cycloalkenyl,} optionally substituted with ^{R 28} _(C 3 ~C _{8) cycloalkenyl,} with C 2 -C ₆ ^{alkynyl, R 28} optionally substituted _(C 2 ~C _{6) alkynyl,} C 3 -C ₈ ^cycloalkyl, optionally substituted with ^{R 28} _(C 3 ~C _{8) ^{cycloalkyl, -OR 25, -S (O)}} r R ²⁵ , —C (O) OH, —C (O) OR ^25a , —C (O) R ²⁶ , —C (O) N (R ^27a ) R ²⁷ , —C (S) N (R ^27a ) R ^{27, -N (R 27a) R} 27, -C (= NOR 25) _{^{R 26, -S (O) 2}} N (R 27a) R 27, ^phenyl, (Z ₂₎ phenyl substituted with _q2, ^naphthyl, (Z ₂₎ is substituted with _q2 naphthyl or D2-1~D2-41 When q represents an integer of 2 or more, each Z may be the same as or different from each other, and when two Zs are adjacent to each other, the two adjacent Zs are − _{CH 2 CH 2 CH 2 -,} - CH 2 CH 2 O -, - CH 2 OCH 2 -, - OCH 2 O -, - CH 2 CH 2 S -, - CH 2 SCH 2 -, - 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 by forming a -OCH ₂ CH ₂ S-, its A 5-membered ring or a 6-membered ring may be formed together with the carbon atom to which each Z is bonded. At this time, the hydrogen atom bonded to each carbon atom forming the ring is a halogen atom, C _{1 to} C _6. alkyl _group, C 1 -C ₆ haloalkyl _group, C 1 -C ₆ alkoxy _group, C 1 -C ₆ alkylthio _group, optionally substituted by C 1 -C ₆ alkylsulfinyl group or a _C 1 -C ₆ alkylsulfonyl group Well,
R ²⁵ , R ^25a and R ²⁶ each independently represent C ₁ -C ₆ alkyl or (C ₁ -C ₆ ) alkyl optionally substituted with R ^32a ,
R ²⁷ and ^{R 27a} represent independently a hydrogen _atom, C 1 -C ₆ alkyl, -S _(O) ^{r R 34} or -C ^{(O) R 34,}
R ²⁸ and R ^28a each independently represent a halogen atom, —OH, —OR ²⁹ , —SH or —S (O) _r R ²⁹ ;
R ²⁹ and R ³³ each independently represent C ₁ -C ₆ alkyl;
R ³² and R ^32a each independently represent a halogen atom, —OR ³³ or —S (O) _r R ³³ ;
R ³⁴ represents C ₁ -C ₆ alkyl, C ₃ -C ₈ cycloalkyl or C ₁ -C ₆ haloalkyl,
D2-1 to D2-41 each represent a ring represented by the following structural formula;

X ² is a halogen atom, cyano, nitro, —OH, —SH, 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 1 -C _{6 alkoxy,} C 1 -C _{6 haloalkoxy,} C 1 -C ₆ alkylthio, C ₁ -C _{6 haloalkylthio,} C 1 -C ₆ alkylsulfinyl represents _Le, C 1 -C _{6 haloalkylsulfinyl,} a C 1 -C ₆ alkylsulfonyl or _C 1 -C ₆ haloalkylsulfonyl, t1, t2 or t4 is 2 or more Each X ² may be the same as or different from each other,
X ^2a is 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,} represents C 3 -C ₈ halocycloalkyl,
Z ² is a halogen atom, cyano, nitro, —OH, —SH, 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 1 -C _{6 alkoxy,} C 1 -C _{6 haloalkoxy,} C 1 -C ₆ alkylthio, C ₁ -C ₆ represents _{haloalkylthio,} C 1 -C _{6 alkylsulfinyl,} C 1 -C _{6 haloalkylsulfinyl,} a C 1 -C ₆ alkylsulfonyl or _C 1 -C ₆ haloalkylsulfonyl, q2 is an integer of 2 or more Each Z may be the same as or different from each other;
n, g1, f1, and t1 each independently represents an integer of 0 to 3,
g2 and t2 each independently represent an integer of 0 to 2,
g3 and t3 each independently represent an integer of 0 to 1,
g4, f4 and t4 each independently represent an integer of 0 to 4,
f5 represents an integer of 0 to 5,
f6 represents an integer of 0 to 6,
f7 represents an integer of 0 to 7,
f8 represents an integer of 0 to 8,
f9 represents an integer of 0 to 9,
q and q2 each independently represent an integer of 1 to 5,
m1, m2 and m4 each independently represents an integer of 0 or 1,
r and r2 each independently represents an integer of 0 to 2; ] The pyrazole derivative represented by these, or its salt.

[2]
A ¹ represents -CR ¹
R ¹ , R ³ and R ⁴ each independently represents a hydrogen atom, a halogen atom or C ₁ -C ₆ alkyl;
R ² represents a pyrazole derivative or a salt thereof according to the above [1], wherein R ² represents a halogen atom or C ₁ -C ₆ alkyl.

[3]
R ¹ represents a hydrogen atom or a halogen atom,
R ³ represents a hydrogen atom, a halogen atom or C ₁ -C ₆ alkyl,
R ⁴ represents a hydrogen atom,
R ^b is (C ₁ -C ₆ ) alkyl optionally substituted with R ^5a , -C (R ⁷ ) = NOH, -C (R ⁷ ) = NOR ⁶ , -C (R ⁷ ) = NR ^8b , -C ^{(= NOR 6)} represents ^{N (R 8a) R 8,} -C (= NR 8b) SR 6a, -N (R 8g) R 8 or ^{-N = C (R 7a) R} 7b,
R ^c represents a hydrogen atom, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted with R ⁵ or —C (O) R ^7c , or R ^c represents R ^b Together, they may form ═C (R ^8c ) R ^8d ,
R ⁵ represents cyano or —OR ¹¹ ;
R ⁶ , R ^6a , R ^7c , R ¹¹ , R ^15a and R ¹⁶ each independently represent C ₁ -C ₆ alkyl;
R ⁷ represents a hydrogen atom, C ₁ -C ₆ alkyl or (C ₁ -C ₆ ) alkyl optionally substituted with R ¹⁴ ,
R ^7a represents C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted with R ¹⁴ , phenyl or phenyl substituted with (Z) _q ;
R ^7b represents a hydrogen atom or C ₁ -C ₆ alkyl, or R ^7b together with R ^7a forms a C ₄ alkylene chain, whereby the carbon atom to which R ^7b and R ^7a are bonded. Together with this, the alkylene chain may contain one sulfur atom,
R ⁸ represents a hydrogen atom or C ₁ -C ₆ alkyl,
R ^8a represents a hydrogen atom,
R ^8b represents a hydrogen atom, —C (O) R ¹² or —C (O) N (R ^13a ) R ¹³ ;
R ^8c represents —OR ¹¹ , —N (R ^13a ) R ^13, or —N (R ^13c ) N (R ^13a ) R ¹³ ;
R ^8d may represent a hydrogen atom or ^{-N (R 13e)} R ^{13d, or, R 8d} may be form an alkylene chain, or alkenylene chain of _{C 4} or _{C 5 C 4} to together with ^{R 8c} May form a 5- or 6-membered ring together with the carbon atom to which R ^8d and R ^8c are bonded, and this alkylene chain or alkenylene chain may contain 1 to 3 sulfur atoms or nitrogen atoms, and halogen Atom, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted with R ¹⁴ , C ₃ -C ₈ cycloalkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, -OR ¹⁵ , optionally substituted by —S (O) _r R ¹⁵ or D1-33,
R ¹² represents a hydrogen atom, C ₁ -C ₆ alkyl or D1-32;
R ^13c , R ^13d and R ^13e represent a hydrogen atom and R ^12a represents (C ₁ -C ₆ ) alkyl optionally substituted with R ^14a , or R ^12a together with R ⁸ By forming an alkylene chain of C _{3 to} C _4, a 5- to 6-membered ring may be formed together with the carbon atom to which R ^12a is bonded and the nitrogen atom to which R ⁸ is bonded, and —S (O) _r R Optionally substituted by ¹⁵ ;
R ¹³ represents a hydrogen atom, C ₁ -C ₆ alkyl or (C ₁ -C ₆ ) alkyl optionally substituted with R ^14a ,
R ^13a represents a hydrogen atom, C ₁ -C ₆ alkyl, —C (O) OR ^15a or —C (O) R ¹⁶ , or R ^13a together with R ¹³ is a C ₄ alkylene chain. To form a 5-membered ring together with the nitrogen atom to which R ^13a and R ¹³ are bonded,
R ¹⁴ represents a halogen atom, _{^{cyano, -OR 15, -S (O)}} r R 15 or -C a ^{(O) OR 15a,}
R ^14a represents a halogen atom or —S (O) _r R ¹⁵ ;
R ¹⁵ represents C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
X ¹ represents a halogen atom or C ₁ -C ₆ alkoxy;
Z _is, C 1 -C ₆ alkoxy or _C 1 -C ₆ alkylthio,
g4 represents an integer of 2;
q represents an integer of 1;
n, m1 and m3 represent 0;
r is a pyrazole derivative according to the above [2] or a salt thereof, wherein r represents an integer of 0 to 2.

[4]
A pest control agent comprising one or more selected from the pyrazole derivatives described in [1] to [3] above and salts thereof as an active ingredient.

[5]
An agrochemical containing one or more selected from the pyrazole derivatives and salts thereof described in [1] to [3] as active ingredients.

[6]
A mammal or avian internal or ectoparasite control agent comprising one or more selected from the pyrazole derivatives described in the above [1] to [3] and salts thereof as an active ingredient.

[7]
An insecticide or acaricide containing as an active ingredient one or more selected from the pyrazole derivatives described in [1] to [3] above and salts thereof.

[8]
The soil treatment agent which contains 1 type, or 2 or more types chosen from the pyrazole derivative and its salt of said [1]-[3] 3 as an active ingredient.

[9]
The soil treatment agent according to the above [8], wherein the soil treatment method is soil irrigation treatment.

  The compound of the present invention has excellent insecticidal / miticidal activity against many agricultural pests, spider mites, mammals or birds, or against insects that have acquired resistance to existing insecticides. Even against this, it exhibits a sufficient control effect. Furthermore, it has little adverse effect on mammals, fish and beneficial insects, has low persistence, and has a light environmental impact.

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

  Regarding the amide structure of the compound of the present invention represented by the general formula (1), it may be present as a tautomer represented by the following formula depending on the type and conditions of the substituent. The invention includes all such structures.

  In addition, the compounds included in the present invention may have geometrical isomers of E-form and Z-form depending on the type of substituent, but the present invention is not limited to these E-form, Z-form or E-form. -A mixture containing the isomer and the Z isomer in an arbitrary ratio is included. In addition, the compounds included in the present invention include optically active substances resulting from the presence of one or more asymmetric carbon atoms, but the present invention includes all optically active substances or racemates.

  Among the compounds included in the present invention, those that can be converted into acid addition salts according to a conventional method include, for example, hydrohalic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, and the like. Salts of inorganic acids such as salts, nitric acid, sulfuric acid, phosphoric acid, chloric acid, perchloric acid, salts of sulfonic acids such as methanesulfonic acid, ethanesulfonic acid, trifluoromethanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, Salts of carboxylic acids such as formic acid, acetic acid, propionic acid, trifluoroacetic acid, fumaric acid, tartaric acid, succinic acid, maleic acid, malic acid, succinic acid, benzoic acid, mandelic acid, ascorbic acid, lactic acid, gluconic acid, citric acid, or A salt of an amino acid such as glutamic acid or aspartic acid can be used.

  Alternatively, among the compounds included in the present invention, those that can be converted into a metal salt according to a conventional method include, for example, alkali metal salts such as lithium, sodium, and potassium, and alkaline earth metals such as calcium, barium, and magnesium. It can be a salt or a salt of aluminum.

  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.

  As a halogen atom in this invention compound, a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom are mentioned. 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, for example, cyclopropyl group, 1-methylcyclopropyl group, 2-methylcyclopropyl group, 2,2-dimethylcyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group and the like. 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 alkylidene represents a linear or branched hydrocarbon group having a carbon number of _a to _b and bonded by a double bond, such as a methylidene group or an ethylidene group. 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.

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.

In the present specification, the notation of di (C _a -C _b alkyl) aminosulfonyl 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 sulfamoyl group substituted by an alkyl group, such as N, N-dimethylsulfamoyl group, N-ethyl-N-methylsulfamoyl group, N, N-diethylsulfamoyl group, N, N-di- Specific examples include (n-propyl) sulfamoyl group, N, N-di (n-butyl) sulfamoyl group and the like, and each is selected within the range of the designated number of carbon atoms.

Herein optionally substituted with ^{R 5} _(C a ^~C _b) ^alkyl, optionally substituted with ^{R 5a} _(C ^{a ~C} _b) ^alkyl, optionally substituted with ^{R 14} _(C a ~ C _b) ^alkyl, optionally substituted with ^{R 14a} _(C ^{a ~C} _b) ^alkyl, optionally substituted with ^{R 28} _(C a ^~C _b) ^alkyl, optionally substituted with ^{R 28a} _{(C a} ~ C _b ) alkyl or (C _a -C _b ) alkyl optionally substituted with R ^32a is represented by any R ⁵ , R ^5a , R ¹⁴ , R ^14a , R ²⁸ , R ^28a or R ^32a 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 ²⁸ , R ^28a or R ^32a on each (C _a -C _b ) alkyl group are present, each R ⁵ , R ^5a , R ¹⁴ , R ^14a , R ²⁸ , R ^28a or R ^32a may be the same or different from each other.

Herein optionally substituted with ^{R 5} _(C a ^~C _b) ^cycloalkyl, optionally substituted with ^{R 14} _(C a ^~C _b) ^cycloalkyl, optionally substituted with ^{R 14a} (C _a -C _b) ^cycloalkyl, optionally substituted with ^{R 28} _(C a ~C _b) is optionally substituted cycloalkyl, or ^{R 28a} _(C ^a ~C _b) notation cycloalkyl or the like, any R ⁵ , R ¹⁴ , R ^14a , R ²⁸ or R ^28a represents a cycloalkyl group having the above-mentioned meaning consisting of a to b carbon atoms in which a hydrogen atom bonded to a carbon atom is optionally substituted; Each selected range of carbon atoms is selected. At this time, when two or more substituents R ⁵ , R ¹⁴ , R ^14a , R ²⁸ or R ^28a on each (C _a -C _b ) cycloalkyl group are present, each R ⁵ , R ¹⁴ , R ^14a , R ²⁸ or R ^28a may be the same as or different from each other, and the substitution position may be a ring structure moiety, a side chain moiety, or both.

Herein optionally substituted with ^{R 5} _(C a ^~C _b) ^alkenyl, optionally substituted with ^{R 14} _(C a ^~C _b) ^alkenyl, optionally substituted with ^{R 14a} _(C ^a ~ C _b) ^alkenyl, optionally substituted with ^{R 28} _(C a _{~C b)} alkenyl or optionally substituted _(C a _{~C b)} representation alkenyl such as in ^{R 28a,} any ^{R 5, R 14} , R ^14a , R ^28, or R ^28a represent an alkenyl group having the above-described meanings of the number of carbon atoms in which a hydrogen atom bonded to a carbon atom is arbitrarily substituted, and each designated carbon atom Selected in a range of numbers. At this time, when two or more substituents R ⁵ , R ¹⁴ , R ^14a , R ²⁸ or R ^28a on each (C _a -C _b ) alkenyl group are present, each R ⁵ , R ¹⁴ , R ^{14a is present.} , R ²⁸ or R ^28a may be the same as or different from each other.

Herein optionally substituted with ^{R 5} _(C a ^~C _b) ^{cycloalkenyl,} optionally substituted with ^{R 14} _(C a ^~C _b) ^{cycloalkenyl,} optionally substituted with ^{R 14a} (C _a -C _b) ^{cycloalkenyl,} optionally substituted with ^{R 28} _(C a ~C _b) is optionally substituted cycloalkenyl or ^{R 28a} _(C ^a ~C _b) representation of such cycloalkenyl, any R ⁵ , R ¹⁴ , R ^14a , R ²⁸ or R ^28a represents a cycloalkenyl group having the above-mentioned meaning consisting of a to b carbon atoms in which a hydrogen atom bonded to a carbon atom is optionally substituted; Each selected range of carbon atoms is selected. At this time, when two or more substituents R ⁵ , R ¹⁴ , R ^14a , R ²⁸ or R ^28a on each (C _a -C _b ) cycloalkenyl group are present, each R ⁵ , R ¹⁴ , R ^14a , R ²⁸ or R ^28a may be the same as or different from each other, and the substitution position may be a ring structure moiety, a side chain moiety, or both.

Herein optionally substituted with ^{R 5} _(C a ^~C _b) alkynylene ^Le, optionally substituted with ^{R 14} _(C a ^~C _b) alkynylene ^Le, optionally substituted with ^{R 14a} _(C a ~C _b) alkynylene ^Le, optionally substituted with ^{R 28} _(C a _{~C b)} is optionally substituted with alkynylene Le or ^{R 28a} _(C ^a _{~C b)} alkynylene Le etc. The notation is an alkyl having the above-mentioned meaning of the number of carbon atoms in which a hydrogen atom bonded to a carbon atom is optionally substituted by any R ⁵ , R ¹⁴ , R ^14a , R ²⁸ or R ^28a . Represents a dil group and is selected for each specified number of carbon atoms. At this time, when there are two or more substituents R ⁵ , R ¹⁴ , R ^14a , R ²⁸ or R ^28a on each (C _a -C _b ) alkynyl group, each R ⁵ , R ¹⁴ , R ^14a , R ²⁸ or R ^28a may be the same as or different from each other.

In the present specification, [R ^12a forms a C _{2 to} C ₆ alkylene chain or a C _{2 to} C ₆ alkenylene chain together with R ⁸ to form a carbon atom to which R ^12a is bonded and a nitrogen to which R ⁸ is bonded. A 4- to 8-membered ring may be formed together with atoms, and this alkylene chain or alkenylene chain may contain one or two oxygen atoms, sulfur atoms or nitrogen atoms.
Specific examples of notation such as azetidin-2-one, pyrrolidin-2-one, pyrrolidine-2,5-dione, oxazolidine-2-one, oxazolidine-2-thione, thiazolidine-2-one, thiazolidine-2 -Thion, imidazolidin-2-one, imidazolidine-2-thione, piperidin-2-one, piperidine-2-thione, piperidine-2,6-dione, etc. Selected.

[R ⁸ represents that R ^8a may form 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. At this time, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom.]
^{[R 7b} and ^{R 7a} is by forming a _C 3 -C ₆ alkylene chain or _C 3 -C ₆ alkenylene chain ^together, form a 4 to 7-membered ring together with the carbon atom ^{to which R 8d} and ^{R 8c} are attached In this case, the alkylene chain or alkenylene chain may contain 1 to 3 oxygen atoms, sulfur atoms, or nitrogen atoms.]
Specific examples of the notation of Lysine-2-ylidene, 2,3-dihydroimidazol-2-ylidene, 2,3-dihydro-1,3,4-thiadiazol-2-ylidene, 1,2-dihydropyridine-2-ylidene, 2,3-dihydro And pyridazine-3-ylidene, 1,2-dihydropyrazin-2-ylidene, 1,2-dihydropyrimidin-2-ylidene, 6H-2,3-dihydro-1,3,4-thiadiazin-2-ylidene Selected within a range of each specified number of atoms.

^{[R 8d} and ^{R 8c} is by forming a _C 4 -C ₆ alkylene chain or _C 4 -C ₆ alkenylene chain ^together, form a 5- to 7-membered ring together with the carbon atom ^{to which R 8d} and ^{R 8c} are attached In this case, the alkylene chain or alkenylene chain may contain 1 to 3 oxygen atoms, sulfur atoms, or nitrogen atoms.]
Specific examples of the notation include, for example, thiazolidine-2-ylidene, 2,3-dihydrothiazol-2-ylidene, imidazolidin-2-ylidene, 2,3-dihydroimidazol-2-ylidene, 2,3-dihydro-1 , 3,4-thiadiazol-2-ylidene, 1,2-dihydropyridin-2-ylidene, 2,3-dihydropyridazine-3-ylidene, 1,2-dihydropyrazin-2-ylidene, 1,2-dihydropyrimidine- Examples include 2-ylidene, 6H-2,3-dihydro-1,3,4-thiadiazin-2-ylidene, and the like, and each is selected within the range of the specified number of atoms.

  The compound of the present invention can be produced by the following method.

  Manufacturing method A

Formula (2) [wherein ^{A 1, R 2, R 3} , R 4 and n are as defined ^{above, R 50} represents an alkyl of _C 1 -C _6. The compound represented by the general formula (3) [wherein R ^b and R ^c represent the same meaning as described above. In general formula (6) [wherein A ¹ , R ^b , R ^c , R ² , R ³ , R ⁴ and n represent the same meaning as described above]. This invention compound represented by this can be synthesize | combined.

  In this reaction, the compound represented by the general formula (3) is used in the range of 0.5 to 50 equivalents relative to the compound represented by the general formula (2). 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 may be carried out without solvent, but a solvent may be used, for example, N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, 1,3-dimethyl-2- Polar solvents such as imidazolinone and water, alcohols such as methanol, ethanol, propanol, 2-propanol and ethylene glycol, ethers 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, and aliphatic hydrocarbons such as pentane and n-hexane. 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.

  Some of the compounds represented by the general formula (3) are known compounds, and some of them are commercially available. Others can be synthesized as shown in Reaction Scheme 2, for example.

By hydrolyzing the compound represented by the general formula (2), the general formula (4) [wherein A ¹ , R ² , R ³ , R ⁴ and n represent the same meaning as described above. Can be obtained. If necessary, a solvent such as methanol, ethanol, dichloromethane, chloroform, diethyl ether, tetrahydrofuran, 1,4-dioxane, ethyl acetate, acetonitrile or the like is used. If necessary, 1 equivalent of the compound represented by the general formula (2) In the presence of 0.1 to 20 equivalents of a base such as potassium carbonate, sodium hydroxide or potassium hydroxide, or an acid such as hydrochloric acid, sulfuric acid or p-toluenesulfonic acid, the temperature ranges from 0 ° C. to the reflux temperature of these solvents. By reacting for from 100 minutes to 100 hours, the compound represented by the general formula (4) can be synthesized.

From the compound represented by the general formula (4), using a halogenating agent or an organic acid halide, the general formula (5) [wherein A ¹ , R ² , R ³ , R ⁴ and n have the same meaning as described above] represents, _{L 2} is a chlorine atom, a bromine ^{atom, -OC (O) R 51,} -OC (O) OR 51 ( wherein ^{R 51} _represents a C 1 -C ₆ alkyl) represents a. ] Can be synthesized.

  As the halogenating agent used in this reaction, thionyl chloride, phosphorus pentachloride or oxalyl chloride can be used, and as the organic acid halide, pivaloyl chloride or isobutyl chloroformate can be used. The compound represented by the general formula (4) Is used in the range of 0.5 to 50 equivalents. If necessary, a base such as triethylamine, pyridine, 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.

  Furthermore, the compound represented by the general formula (5) can be reacted with the compound represented by the general formula (3) to synthesize the compound represented by the general formula (6). If necessary, a base of 0.5 to 50 equivalents of potassium carbonate, triethylamine, pyridine, 4- (dimethylamino) pyridine and the like can be used with respect to 1 equivalent of the compound represented by the general formula (5).

  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, 1 equivalent of the compound represented by the general formula (4) is reacted with 0.5 to 50 equivalents of the compound represented by the general formula (3) to synthesize the compound represented by the general formula (6). can do.

  If necessary, in the presence of a base such as 0.5 to 50 equivalents of potassium carbonate, triethylamine, pyridine, 4- (dimethylamino) pyridine with respect to 1 equivalent of the compound represented by the general formula (4), the general formula (4) 0.5 to 50 equivalents of WSC {1-ethyl-3- (3-dimethylaminopropyl) -carbodiimide hydrochloride}, CDI (carbonyldiimidazole) and the like are used with respect to 1 equivalent of the compound represented by May be.

  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 B

The compound represented by the general formula (4) and the general formula (8) [wherein R ^d , R ¹³ and R ^13a represent the same meaning as described above. The compound represented by general formula (9) [in the formula, A ¹ , R ² , R ³ , R ⁴ , R ^d , R ¹³ , R ^13a and n] Represents the same meaning as described above. ] Can be synthesized. Alternatively, the compound represented by general formula (5) and the compound represented by general formula (8) may be reacted in the same manner as in Production Method A to synthesize the compound represented by general formula (9). it can.

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

  Manufacturing method C

1 equivalent of the compound represented by the general formula (6) and 0.5 to 50 equivalents of diphosphorus pentasulfide, diphosphorus pentasulfide-HMDO (hexamethyldisiloxane), Lawesson's Reagent; 2,4- Reaction with a sulfiding agent such as bis (4-methoxyphenyl) -1,3,2,4-dithiadiphosphetane = 2,4-disulfide) gives general formula (7) [wherein A ¹ , R ^b , R ^c , R ² , R ³ , R ⁴ and n represent the same meaning as described above. ] Can be synthesized.

  If necessary, a base such as 0.5 to 50 equivalents of sodium bicarbonate, triethylamine, pyridine and the like can be used with respect to 1 equivalent of the compound represented by the general formula (6).

  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 D

General formula (2-12) [In formula, R < ³ >, R < ⁴ >, R < ^b > and R ^<c > represent the same meaning as the above. And a compound represented by the general formula (2-2) [wherein A ¹ , R ² and n 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 group or —B (OR ⁵¹ ) ₂ group (wherein R ⁵¹ represents a hydrogen atom or C _{1 to} C ₆ alkyl which may be the same or different, or two R ⁵¹ together) It represents a may be formed) - -CH ₂ CH ₂ - or _{-C (CH 3) 2 C (} CH 3) 2. The compound of the present invention represented by the general formula (6) can be obtained by reacting the compound represented by formula (6).

  The amount of the compound represented by the general formula (2-2) can be used in the range of 0.8 to 5 equivalents relative to 1 equivalent of the compound represented by the general formula (2-12).

  Some of the compounds represented by the general formula (2-2) used here are known compounds, and some of them are available as commercial products. Others can be synthesized according to the methods described in the literature.

  If necessary, catalysts and bases can be used. 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, or copper metal, copper acetate (I). And copper catalysts such as copper (II) acetate, copper (I) oxide, copper (II) oxide and copper iodide. The usage-amount of a catalyst is 0.001-1.0 equivalent with respect to 1 equivalent of compounds represented by General formula (2-12), Preferably, it is 0.01-0.5 equivalent, More preferably, it is 0.05. It can be used in the range of ~ 0.2 equivalent.

  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 the range of 0.1-10.0 equivalent with respect to 1 equivalent of compounds represented by General formula (2-12).

  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 −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 reaction from production method A to production method D may be carried out in an inert gas atmosphere such as nitrogen or argon if necessary.

  In the reaction from production method A to production method D, the reaction mixture after completion of the reaction is directly concentrated, or dissolved in an organic solvent, concentrated after washing with water, or poured into ice water and concentrated after extraction with an organic solvent, followed by normal post-treatment. The objective compound of the present invention 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.

  Reaction formula 1

General formula (2-1) [wherein R ³ and R ⁴ represent the same meaning as described above, and R ⁵⁰ represents a C1-C6 alkyl group. ] Can be produced by a known method such as Sinlet 2004, Vol. 4, 703.

  By reacting the compound represented by the general formula (2-1) and the compound represented by the general formula (2-2) in the same manner as in the production method D, the compound represented by the general formula (2) is represented. Compounds can be synthesized.

  Reaction formula 2

General formula (2-6) [wherein R ³ , R ⁴ and R ⁵⁰ represent the same meaning as described above, and P ¹ represents protection of tertiary butyl, benzyl, 4-methoxybenzyl, acetyl, methoxymethyl or methylthiomethyl, etc. Represents a group. ] Can be synthesized by known methods such as Journal of Heterocyclic Chemistry 1987, 24, 693.

By hydrolyzing the compound represented by the general formula (2-6) according to a known method known in the literature, the general formula (2-7) [wherein R ³ , R ⁴ and P ¹ are Means the same. The compound represented by this can be manufactured.

Subsequently, from the compound represented by the general formula (2-7), using the same method as the production method A, the general formula (2-8) [wherein R ³ , R ⁴ , R ^b , R ^c and P ¹ represents the same meaning as described above. ] Can be synthesized.

Next, by deprotecting the compound represented by the general formula (2-8) with an acid or a base, the general formula (2-12) [wherein R ³ , R ⁴ , R ^b and R ^c are as defined above. Represents the same meaning. ] Can be synthesized.

  Reaction formula 3

Formula (3-1) [wherein R ¹⁵ represents the same meaning as described above. In accordance with a known method described in the literature, for example, the method described in Journal of Medicinal Chemistry 1998, 41, 2835, etc., the compound represented by the general formula (3 -2) [wherein R ¹⁵ represents the same meaning as described above. ] Can be synthesized.

  Some of the compounds represented by the general formula (3-1) used here are known compounds, and some of them are available as commercial products. Others can be synthesized according to the general synthesis methods described in the literature.

Subsequently, the compound represented by the general formula (3-2) was prepared according to a known method described in the literature, for example, the method described in European Journal of Medicinal Chemistry 1992, 28, 765, etc. 3-3) [wherein R ¹⁵ represents the same meaning as described above. And a compound represented by formula (3-4) [wherein R ⁶ and R ¹⁵ represent the same meaning as described above. ] Can be synthesized.

  Some of the compounds represented by formula (3-3) used here are known compounds, and some of them are available as commercial products. Others can be synthesized according to the general synthesis methods described in the literature.

  Specific examples of the active compound included in the present invention include compounds shown in Tables 1 and 2. However, the compounds in Table 1 and Table 2 are for illustrative purposes, and the present invention is not limited to these. 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, D1-1a to D1-107a represent the following structural formulas: D1-1c, D1-1d, D1-2c, D1-2d, D1-3b, D1-4c, D1-4d, D1-5d, D1-5e, D1-5f, D1-6d, D1-6e, D1-6f, D1-7b, D1-8d, D1-8e, D1-8f, D1-9d, D1-9e, D1-9f, D1- 10d, D1-10e, D1-10f, D1-11b, D1-12d, D1-12e, D1-12f, D1-20b, D1-22b, D1-24b, D1-26b, D1-32b, D1-33b, D1-34b, D1-35c, D1-35d, D1-36b, D1-37b, D1-38b, numbers written in the structural formula of D1-39b represents the substitution position of ^{X 1,} the D1-105b The number given in the structural formula is Z Indicates the replacement position.

[Table 1]

――――――――――――――――――――――――
R ^c R ^b
――――――――――――――――――――――――
H CH = NOMe
HC (= NOH) CF ₃
H CH ₂ CH = NOH
H CH ₂ CH = NOMe
Me CH ₂ CH = NOMe
H CH ₂ CH = NOEt
H CH ₂ CH = NOPr-n
H CH ₂ CH = NOPr-c
H CH ₂ CH = NOCH ₂ CH = CH ₂
H CH ₂ CH = NOCH ₂ CH≡CH
H CH ₂ CH = NOCH ₂ Ph
H CH ₂ CH = NOCH ₂ CF ₃
H CH ₂ CH = NOCH ₂ CF ₂ CF ₃
H CH ₂ CH = NOCH ₂ CF ₂ CF ₂ H
H CH ₂ CH = NOCH ₂ CN
H CH ₂ CH = NOCH ₂ CH ₂ OCH ₃
H CH ₂ CH = NOCH ₂ CH ₂ SCH ₃
H CH ₂ CH = NOCH ₂ (D1-1a)
H CH ₂ CH = NOCH ₂ (D1-1b)
H CH ₂ CH = NOCH ₂ (D1-2a)
H CH ₂ CH = NOCH ₂ (D1-2b)
H CH ₂ CH = NOCH ₂ (D1-4a)
H CH ₂ CH = NOCH ₂ (D1-4b)
H CH ₂ CH = NOCH ₂ (D1-5a)
H CH ₂ CH = NOCH ₂ (D1-5b)
H CH ₂ CH = NOCH ₂ (D1-5c)
H CH ₂ CH = NOCH ₂ (D1-6a)
H CH ₂ CH = NOCH ₂ (D1-6b)
H CH ₂ CH = NOCH ₂ (D1-6c)
H CH ₂ CH = NOCH ₂ (D1-7a)
H CH ₂ CH = NOCH ₂ (D1-8a)
H CH ₂ CH = NOCH ₂ (D1-8b)
H CH ₂ CH = NOCH ₂ (D1-8c)
H CH ₂ CH = NOCH ₂ (D1-9a)
H CH ₂ CH = NOCH ₂ (D1-9b)
H CH ₂ CH = NOCH ₂ (D1-9c)
H CH ₂ CH = NOCH ₂ (D1-10a)
H CH ₂ CH = NOCH ₂ (D1-10b)
H CH ₂ CH = NOCH ₂ (D1-10c)
H CH ₂ CH = NOCH ₂ (D1-12a)
H CH ₂ CH = NOCH ₂ (D1-12b)
H CH ₂ CH = NOCH ₂ (D1-12c)
H CH ₂ CH = NOCH ₂ (D1-13a)
H CH ₂ CH = NOCH ₂ (D1-13b)
H CH ₂ CH = NOCH ₂ (D1-14a)
H CH ₂ CH = NOCH ₂ (D1-14b)
H CH ₂ CH = NOCH ₂ (D1-15a)
H CH ₂ CH = NOCH ₂ (D1-15b)
H CH ₂ CH = NOCH ₂ (D1-16a)
H CH ₂ CH = NOCH ₂ (D1-17a)
H CH ₂ CH = NOCH ₂ (D1-18a)
H CH ₂ CH = NOCH ₂ (D1-19a)
H CH ₂ CH = NOCH ₂ (D1-20a)
H CH ₂ CH = NOCH ₂ (D1-21a)
H CH ₂ CH = NOCH ₂ (D1-21b)
H CH ₂ CH = NOCH ₂ (D1-23a)
H CH ₂ CH = NOCH ₂ (D1-23b)
H CH ₂ CH = NOCH ₂ (D1-25a)
H CH ₂ CH = NOCH ₂ (D1-27a)
H CH ₂ CH = NOCH ₂ (D1-30a)
H CH ₂ CH = NOCH ₂ (D1-31a)
H CH ₂ CH = NOCH ₂ (D1-32a)
Me CH ₂ CH = NOCH ₂ (D1-32a)
Et CH ₂ CH = NOCH ₂ (D1-32a)
n-Pr CH ₂ CH = NOCH ₂ (D1-32a)
i-Pr CH ₂ CH = NOCH ₂ (D1-32a)
CH ₂ OCH ₃ CH ₂ CH = NOCH ₂ (D1-32a)
CH ₂ CH ₂ OEt CH ₂ CH = NOCH ₂ (D1-32a)
CH ₂ SCH ₃ CH ₂ CH = NOCH ₂ (D1-32a)
CH ₂ CN CH ₂ CH = NOCH ₂ (D1-32a)
CH ₂ CO ₂ Me CH ₂ CH = NOCH ₂ (D1-32a)
CH ₂ CO ₂ Et CH ₂ CH = NOCH ₂ (D1-32a)
CH ₂ CH = CH ₂ CH ₂ CH = NOCH ₂ (D1-32a)
CH ₂ CH≡CH CH ₂ CH = NOCH ₂ (D1-32a)
C (O) CH ₃ CH ₂ CH = NOCH ₂ (D1-32a)
C (O) Et CH ₂ CH = NOCH ₂ (D1-32a)
C (O) Pr-n CH ₂ CH = NOCH ₂ (D1-32a)
C (O) Pr-c CH ₂ CH = NOCH ₂ (D1-32a)
C (O) Bu-t CH ₂ CH = NOCH ₂ (D1-32a)
C (O) CH ₂ OCH ₃ CH ₂ CH = NOCH ₂ (D1-32a)
C (O) CH ₂ SCH ₃ CH ₂ CH = NOCH ₂ (D1-32a)
C (O) OMe CH ₂ CH = NOCH ₂ (D1-32a)
C (O) OEt CH ₂ CH = NOCH ₂ (D1-32a)
C (O) CH ₂ CH ₂ CH ₂ CH = NOCH ₂ (D1-32a)
C (O) CH ₂ CH ₂ CH ₂ CH = NOCH ₂ (D1-32a)
C (O) OCH ₂ CH = CH ₂ CH ₂ CH = NOCH ₂ (D1-32a)
C (O) SCH ₃ CH ₂ CH = NOCH ₂ (D1-32a)
C (S) OCH ₃ CH ₂ CH = NOCH ₂ (D1-32a)
C (S) SCH ₃ CH ₂ CH = NOCH ₂ (D1-32a)
SMe CH ₂ CH = NOCH ₂ (D1-32a)
SPh CH ₂ CH = NOCH ₂ (D1-32a)
SNEt ₂ CH ₂ CH = NOCH ₂ (D1-32a)
SO ₂ Me CH ₂ CH = NOCH ₂ (D1-32a)
SO ₂ Et CH ₂ CH = NOCH ₂ (D1-32a)
SO ₂ Ph CH ₂ CH = NOCH ₂ (D1-32a)
SO ₂ NMe ₂ CH ₂ CH = NOCH ₂ (D1-32a)
NH ₂ CH ₂ CH = NOCH ₂ (D1-32a)
NHMe CH ₂ CH = NOCH ₂ (D1-32a)
NHCHO CH ₂ CH = NOCH ₂ (D1-32a)
NHC (O) CH ₃ CH ₂ CH = NOCH ₂ (D1-32a)
NHC (O) CF ₃ CH ₂ CH = NOCH ₂ (D1-32a)
NHC (O) OCH ₃ CH ₂ CH = NOCH ₂ (D1-32a)
N = C (CH ₃ ) ₂ CH ₂ CH = NOCH ₂ (D1-32a)
N = CHPh CH ₂ CH = NOCH ₂ (D1-32a)
H CH ₂ CH = NOCH ₂ (D1-33a)
H CH ₂ CH = NOCH ₂ (D1-34a)
H CH ₂ CH = NOCH ₂ (D1-35a)
H CH ₂ CH = NOCH ₂ (D1-35b)
H CH ₂ CH = NOCH ₂ (D1-36a)
H CH ₂ CH = NOCH ₂ (D1-37a)
Me CH ₂ CH = NOCH ₂ (D1-37a)
Et CH ₂ CH = NOCH ₂ (D1-37a)
n-Pr CH ₂ CH = NOCH ₂ (D1-37a)
i-Pr CH ₂ CH = NOCH ₂ (D1-37a)
CH ₂ OCH ₃ CH ₂ CH = NOCH ₂ (D1-37a)
CH ₂ CH ₂ OEt CH ₂ CH = NOCH ₂ (D1-37a)
CH ₂ SCH ₃ CH ₂ CH = NOCH ₂ (D1-37a)
CH ₂ CN CH ₂ CH = NOCH ₂ (D1-37a)
CH ₂ CO ₂ Me CH ₂ CH = NOCH ₂ (D1-37a)
CH ₂ CO ₂ Et CH ₂ CH = NOCH ₂ (D1-37a)
CH ₂ CH = CH ₂ CH ₂ CH = NOCH ₂ (D1-37a)
CH ₂ CH≡CH CH ₂ CH = NOCH ₂ (D1-37a)
C (O) CH ₃ CH ₂ CH = NOCH ₂ (D1-37a)
C (O) Et CH ₂ CH = NOCH ₂ (D1-37a)
C (O) Pr-n CH ₂ CH = NOCH ₂ (D1-37a)
C (O) Pr-c CH ₂ CH = NOCH ₂ (D1-37a)
C (O) Bu-t CH ₂ CH = NOCH ₂ (D1-37a)
C (O) CH ₂ OCH ₃ CH ₂ CH = NOCH ₂ (D1-37a)
C (O) CH ₂ SCH ₃ CH ₂ CH = NOCH ₂ (D1-37a)
C (O) OMe CH ₂ CH = NOCH ₂ (D1-37a)
C (O) OEt CH ₂ CH = NOCH ₂ (D1-37a)
C (O) CH ₂ CH ₂ CH ₂ CH = NOCH ₂ (D1-37a)
C (O) CH ₂ CH ₂ CH ₂ CH = NOCH ₂ (D1-37a)
C (O) OCH ₂ CH = CH ₂ CH ₂ CH = NOCH ₂ (D1-37a)
C (O) SCH ₃ CH ₂ CH = NOCH ₂ (D1-37a)
C (S) OCH ₃ CH ₂ CH = NOCH ₂ (D1-37a)
C (S) SCH ₃ CH ₂ CH = NOCH ₂ (D1-37a)
SMe CH ₂ CH = NOCH ₂ (D1-37a)
SPh CH ₂ CH = NOCH ₂ (D1-37a)
SNEt ₂ CH ₂ CH = NOCH ₂ (D1-37a)
SO ₂ Me CH ₂ CH = NOCH ₂ (D1-37a)
SO ₂ Et CH ₂ CH = NOCH ₂ (D1-37a)
SO ₂ Ph CH ₂ CH = NOCH ₂ (D1-37a)
SO ₂ NMe ₂ CH ₂ CH = NOCH ₂ (D1-37a)
NH ₂ CH ₂ CH = NOCH ₂ (D1-37a)
NHMe CH ₂ CH = NOCH ₂ (D1-37a)
NHCHO CH ₂ CH = NOCH ₂ (D1-37a)
NHC (O) CH ₃ CH ₂ CH = NOCH ₂ (D1-37a)
NHC (O) CF ₃ CH ₂ CH = NOCH ₂ (D1-37a)
NHC (O) OCH ₃ CH ₂ CH = NOCH ₂ (D1-37a)
N = C (CH ₃ ) ₂ CH ₂ CH = NOCH ₂ (D1-37a)
N = CHPh CH ₂ CH = NOCH ₂ (D1-37a)
H CH ₂ CH = NOCH ₂ (D1-38a)
H CH ₂ CH = NOCH ₂ (D1-39a)
H CH ₂ CH = NOCH ₂ (D1-40a)
H CH ₂ CH = NOCH ₂ (D1-41a)
H CH ₂ CH = NOCH ₂ (D1-42a)
H CH ₂ CH = NOCH ₂ (D1-43a)
H CH ₂ CH = NOCH ₂ (D1-45a)
H CH ₂ CH = NOCH ₂ (D1-46a)
H CH ₂ CH = NOCH ₂ (D1-49a)
H CH ₂ CH = NOCH ₂ (D1-51a)
H CH ₂ CH = NOCH ₂ (D1-53a)
H CH ₂ CH = NOCH ₂ (D1-59a)
H CH ₂ CH = NOCH ₂ (D1-61a)
H CH ₂ CH = NOCH ₂ (D1-63a)
H CH ₂ CH = NOCH ₂ (D1-68a)
H CH ₂ CH = NOCH ₂ (D1-75a)
H CH ₂ CH = NOCH ₂ (D1-76a)
H CH ₂ CH = NOCH ₂ (D1-76b)
H CH ₂ CH = NOCH ₂ (D1-77a)
H CH ₂ CH = NOCH ₂ (D1-77b)
H CH ₂ CH = NOCH ₂ (D1-78a)
H CH ₂ CH = NOCH ₂ (D1-78b)
H CH ₂ CH = NOCH ₂ (D1-79a)
H CH ₂ CH = NOCH ₂ (D1-81a)
H CH ₂ CH = NOCH ₂ (D1-82a)
H CH ₂ CH = NOCH ₂ (D1-84a)
H CH ₂ CH = NOCH ₂ (D1-85a)
H CH ₂ CH = NOCH ₂ (D1-87a)
H CH ₂ CH = NOCH ₂ (D1-90a)
H CH ₂ CH = NOCH ₂ (D1-100a)
H CH ₂ CH = NOCH ₂ (D1-100b)
H CH ₂ CH = NOCH ₂ (D1-100c)
H CH ₂ CH = NOCH ₂ (D1-100d)
H CH ₂ CH = NOCH ₂ (D1-100e)
H CH ₂ CH = NOCH ₂ (D1-101a)
H CH ₂ CH = NOCH ₂ (D1-101b)
H CH ₂ CH = NOCH ₂ (D1-101c)
H CH ₂ CH = NOCH ₂ (D1-101d)
H CH ₂ CH = NOCH ₂ (D1-102a)
H CH ₂ CH = NOCH ₂ (D1-102b)
H CH ₂ CH = NOCH ₂ (D1-102c)
H CH ₂ CH = NOCH ₂ (D1-102d)
H CH ₂ CH = NOCH ₂ (D1-102e)
H CH ₂ CH = NOCH ₂ (D1-102f)
H CH ₂ CH = NOCH ₂ (D1-103a)
H CH ₂ CH = NOCH ₂ (D1-104a)
H CH ₂ CH = NOCH ₂ (D1-105a)
H CH ₂ C (Me) = NOH
H CH ₂ C (Me) = NOMe
H CH ₂ C (Me) = NOEt
H CH ₂ C (Me) = NOPr-n
H CH ₂ C (Me) = NOPr-c
H CH ₂ C (Me) = NOCH ₂ CH = CH ₂
H CH ₂ C (Me) = NOCH ₂ CH≡CH
H CH ₂ C (Me) = NOCH ₂ Ph
H CH ₂ C (Me) = NOCH ₂ CF ₃
H CH ₂ C (Me) = NOCH ₂ CF ₂ CF ₃
H CH ₂ C (Me) = NOCH ₂ CF ₂ CF ₂ H
H CH ₂ C (Me) = NOCH ₂ CN
H CH ₂ C (Me) = NOCH ₂ CH ₂ OCH ₃
H CH ₂ C (Me) = NOCH ₂ CH ₂ SCH ₃
HC (Me) ₂ CH = NOMe
H CH ₂ CH ₂ CH = NOMe
H CH ₂ CH ₂ CH ₂ CH = NOMe
H CH ₂ C (D1-1a) = NOMe
H CH ₂ C (D1-1b) = NOMe
H CH ₂ C (D1-2a) = NOMe
H CH ₂ C (D1-2b) = NOMe
H CH ₂ C (D1-5a) = NOMe
H CH ₂ C (D1-5b) = NOMe
H CH ₂ C (D1-5c) = NOMe
H CH ₂ C (D1-6a) = NOMe
H CH ₂ C (D1-6b) = NOMe
H CH ₂ C (D1-6c) = NOMe
H CH ₂ C (D1-7a) = NOMe
H CH ₂ C (D1-8a) = NOMe
H CH ₂ C (D1-8b) = NOMe
H CH ₂ C (D1-8c) = NOMe
H CH ₂ C (D1-9a) = NOMe
H CH ₂ C (D1-9b) = NOMe
H CH ₂ C (D1-9c) = NOMe
H CH ₂ C (D1-10a) = NOMe
H CH ₂ C (D1-10b) = NOMe
H CH ₂ C (D1-10c) = NOMe
H CH ₂ C (D1-11a) = NOMe
H CH ₂ C (D1-12a) = NOMe
H CH ₂ C (D1-12b) = NOMe
H CH ₂ C (D1-12c) = NOMe
H CH ₂ C (D1-13a) = NOMe
H CH ₂ C (D1-13b) = NOMe
H CH ₂ C (D1-14a) = NOMe
H CH ₂ C (D1-14b) = NOMe
H CH ₂ C (D1-15a) = NOMe
H CH ₂ C (D1-15b) = NOMe
H CH ₂ C (D1-16a) = NOMe
H CH ₂ C (D1-17a) = NOMe
H CH ₂ C (D1-18a) = NOMe
H CH ₂ C (D1-19a) = NOMe
H CH ₂ C (D1-21a) = NOMe
H CH ₂ C (D1-21b) = NOMe
H CH ₂ C (D1-22a) = NOMe
H CH ₂ C (D1-23a) = NOMe
H CH ₂ C (D1-23b) = NOMe
H CH ₂ C (D1-24a) = NOMe
H CH ₂ C (D1-25a) = NOMe
H CH ₂ C (D1-27a) = NOMe
H CH ₂ C (D1-30a) = NOMe
H CH ₂ C (D1-31a) = NOMe
H CH ₂ C (D1-32a) = NOMe
H CH ₂ C (D1-34a) = NOMe
H CH ₂ C (D1-36a) = NOMe
H CH ₂ C (D1-37a) = NOMe
H CH ₂ C (D1-41a) = NOMe
H CH ₂ C (D1-43a) = NOMe
H CH ₂ C (D1-45a) = NOMe
H CH ₂ C (D1-46a) = NOMe
H CH ₂ C (D1-49a) = NOMe
H CH ₂ C (D1-51a) = NOMe
H CH ₂ C (D1-53a) = NOMe
H CH ₂ C (D1-59a) = NOMe
H CH ₂ C (D1-61a) = NOMe
H CH ₂ C (D1-63a) = NOMe
H CH ₂ C (D1-68a) = NOMe
H CH ₂ C (D1-75a) = NOMe
H CH ₂ C (D1-76a) = NOMe
H CH ₂ C (D1-76b) = NOMe
H CH ₂ C (D1-77a) = NOMe
H CH ₂ C (D1-77b) = NOMe
H CH ₂ C (D1-78a) = NOMe
H CH ₂ C (D1-78b) = NOMe
H CH ₂ C (D1-79a) = NOMe
H CH ₂ C (D1-81a) = NOMe
H CH ₂ C (D1-82a) = NOMe
H CH ₂ C (D1-84a) = NOMe
H CH ₂ C (D1-85a) = NOMe
H CH ₂ C (D1-87a) = NOMe
H CH ₂ C (D1-90a) = NOMe
H CH ₂ C (D1-100a) = NOMe
H CH ₂ C (D1-100b) = NOMe
H CH ₂ C (D1-100c) = NOMe
H CH ₂ C (D1-100d) = NOMe
H CH ₂ C (D1-100e) = NOMe
H CH ₂ C (D1-101a) = NOMe
H CH ₂ C (D1-101b) = NOMe
H CH ₂ C (D1-101c) = NOMe
H CH ₂ C (D1-101d) = NOMe
H CH ₂ C (D1-102a) = NOMe
H CH ₂ C (D1-102b) = NOMe
H CH ₂ C (D1-102c) = NOMe
H CH ₂ C (D1-102d) = NOMe
H CH ₂ C (D1-102e) = NOMe
H CH ₂ C (D1-102f) = NOMe
H CH ₂ C (D1-103a) = NOMe
H CH ₂ C (D1-104a) = NOMe
H CH ₂ C (D1-107a) = NOMe
H CH ₂ C (O) NHCH ₂ CF ₃
CH ₂ OCH ₃ CH ₂ C (O) NHCH ₂ CF ₃
CH ₂ CN CH ₂ C (O) NHCH ₂ CF ₃
CH ₂ CO ₂ Me CH ₂ C (O) NHCH ₂ CF ₃
CH ₂ CO ₂ Et CH ₂ C (O) NHCH ₂ CF ₃
CH ₂ CH = CH ₂ CH ₂ C (O) NHCH ₂ CF ₃
CH ₂ CH≡CH CH ₂ C (O) NHCH ₂ CF ₃
C (O) Me CH ₂ C (O) NHCH ₂ CF ₃
C (O) OMe CH ₂ C (O) NHCH ₂ CF ₃
H CH ₂ C (O) N (Me) CH ₂ CF ₃
H CH (Me) C (O) NHCH ₂ CF ₃
HC (Me) ₂ C (O) NHCH ₂ CF ₃
H CH (Et) C (O) NHCH ₂ CF ₃
H CH (i-Pr) C (O) NHCH ₂ CF ₃
H CH (CH ₂ OCH ₃ ) C (O) NHCH ₂ CF ₃
H CH (CH ₂ SCH ₃ ) C (O) NHCH ₂ CF ₃
H CH (Ph) C (O) NHCH ₂ CF ₃
H CH (CH ₂ Ph) C (O) NHCH ₂ CF ₃
H NHC (O) CH ₂ SMe
H NHC (O) CH ₂ S (O) Me
H NHC (O) CH ₂ S (O) ₂ Me
H NHC (O) CH (Me) CH ₂ SMe
H NHC (O) CH (Me) SMe
H NHSO ₂ Me
HN (Me) SO ₂ Me
HN (Me) C (O) CH ₂ SMe
HN (Me) C (O) CH ₂ S (O) Me
HN (Me) C (O) CH ₂ S (O) ₂ Me
Me N (Me) C (O) CH ₂ SMe
HN (Me) C (O) CH (Me) SMe
HN (Me) C (O) CH (Me) CH ₂ SMe
H NHC (O) NHCH ₂ CH ₂ SMe
H NHC (O) NHCH ₂ CH ₂ SEt
H NHC (O) NHCH ₂ CH ₂ CH ₂ SMe
H NHC (S) NHCH ₂ CH ₂ CH ₂ SMe
HN = CHMe
HN = C (Me) ₂
C (O) Bu-t N = C (Me) ₂
HN = CHPh
HN = CHCH ₂ SMe
HN = C (Me) CH (Me) SMe
HN = C (Me) CH (Me) S (O) Me
HN = C (Me) CH (Me) S (O) ₂ Me
C (O) Me N = C (Me) CH (Me) SMe
HN = CHCH ₂ CF ₃
HN = C (Me) CH ₂ CF ₃
HN (D1-77c)
HN = CH {D1-105b (4-OMe)}
Me N = CH {D1-105b (4-OMe)}
Et N = CH {D1-105b (4-OMe)}
HN = CH {D1-105b (4-SMe)}
HC (= NCN) CH ₂ SMe
HC (= NCN) CH ₂ S (O) Me
HC (= NCN) CH ₂ S (O) ₂ Me
HC {= NC (O) OMe} CH ₂ SMe
HC {= NC (O) OMe} CH ₂ S (O) Me
HC {= NC (O) OMe} CH ₂ S (O) ₂ Me
H D1-100b
H D1-100f (SMe)
H D1-100f {S (O) Me}
H D1-100f {S (O) ₂ Me}
H D1-101b
H D1-101e (SMe)
H D1-101e {S (O) Me}
H D1-101e {S (O) ₂ Me}
= C (NH ₂ ) OMe
= CHN (Me) ₂
= C (NH ₂ ) N (Me) ₂
= C (NH ₂ ) NHOMe
= C (NH ₂ ) NHCH ₂ CF ₃
= C (NH ₂ ) NHNHC (O) OMe
= C (NH ₂ ) NHNHC (O) Me
= C (NH ₂ ) N (Et) ₂
= C (NH ₂ ) N (D1-100a)
D1-83b (Me)
D1-83b (Et)
D1-83b (CH ₂ C≡CH)
D1-83b {CH ₂ C (O) OEt}
D1-83b (CH ₂ CH = CH ₂ )
D1-83b (CH ₂ CN)
D1-83b (CH ₂ OMe)
D1-83b (Pr-c)
D1-83c (Me)
D1-83c (CH ₂ CH = CH ₂ )
D1-83d (CH ₂ CH = CH ₂ )
D1-83b (OCH ₂ CH ₂ CF ₃ )
D1-83b (CH ₂ CF ₃ )
D1-83f (X ^1a = Me, X ^1b = SMe)
D1-83f (X ^1a = Me, X ^1b = CF ₃ )
D1-83g (X ^1a = Me, X ^1b = SMe)
D1-83e (X ^1a = Me, X ^1b = Me)
D1-101f (Me)
D1-83e (X ^1a = Me, X ^1b = Cl)
――――――――――――――――――――――――
[Table 2]

――――――――――――――――――――――――
R^c               R^d
――――――――――――――――――――――――
H SMe
H S (O) Me
H S (O)₂Me
H CH₂CF_Three
H CH₂CN
H CH₂SMe
Me CH₂SMe
Et CH₂SMe
n-Pr CH₂SMe
i-Pr CH₂SMe
c-Pen CH₂SMe
C (O) OMe CH₂SMe
C (O) Me CH₂SMe
C (O) CF_Three         CH₂SMe
C (O) NMe₂        CH₂SMe
SO₂Me CH₂SMe
S (O)₂CF_Three         CH₂SMe
CH₂CH = C (Cl)₂     CH₂SMe
CH₂CH = CH₂        CH₂SMe
CH₂C≡CH CH₂SMe
CH₂Pr-c CH₂SMe
CH₂CF_Three           CH₂SMe
CH₂CN CH₂SMe
CH₂C (O) OMe CH₂SMe
CH₂C (O) Me CH₂SMe
CH₂OMe CH₂SMe
CH₂SMe CH₂SMe
CH₂Ph CH₂SMe
CH₂(D-105a) CH₂SMe
CH₂OC (O) Me CH₂SMe
SCCl_Three           CH₂SMe
CH₂SiMe_Three         CH₂SMe
CH₂C (NOMe) Me CH₂SMe
H CH₂S (O) Me
H CH₂S (O) Me
Me CH₂S (O) Me
Et CH₂S (O) Me
n-Pr CH₂S (O) Me
i-Pr CH₂S (O) Me
c-Pen CH₂S (O) Me
C (O) OMe CH₂S (O) Me
C (O) Me CH₂S (O) Me
C (O) CF_Three         CH₂S (O) Me
C (O) NMe₂        CH₂S (O) Me
SO₂Me CH₂S (O) Me
S (O)₂CF_Three         CH₂S (O) Me
CH₂CH = C (Cl)₂     CH₂S (O) Me
CH₂CH = CH₂        CH₂S (O) Me
CH₂C≡CH CH₂S (O) Me
CH₂Pr-c CH₂S (O) Me
CH₂CF_Three           CH₂S (O) Me
CH₂CN CH₂S (O) Me
CH₂C (O) OMe CH₂S (O) Me
CH₂C (O) Me CH₂S (O) Me
CH₂OMe CH₂S (O) Me
CH₂SMe CH₂S (O) Me
CH₂Ph CH₂S (O) Me
CH₂(D-105a) CH₂S (O) Me
CH₂OC (O) Me CH₂S (O) Me
SCCl_Three           CH₂S (O) Me
CH₂SiMe_Three         CH₂S (O) Me
CH₂C (NOMe) Me CH₂S (O) Me
H CH₂S (O)₂Me
Me CH₂S (O)₂Me
Et CH₂S (O)₂Me
n-Pr CH₂S (O)₂Me
i-Pr CH₂S (O)₂Me
c-Pen CH₂S (O)₂Me
C (O) OMe CH₂S (O)₂Me
C (O) Me CH₂S (O)₂Me
C (O) CF_Three         CH₂S (O)₂Me
C (O) NMe₂        CH₂S (O)₂Me
SO₂Me CH₂S (O)₂Me
S (O)₂CF_Three         CH₂S (O)₂Me
CH₂CH = C (Cl)₂     CH₂S (O)₂Me
CH₂CH = CH₂        CH₂S (O)₂Me
CH₂C≡CH CH₂S (O)₂Me
CH₂Pr-c CH₂S (O)₂Me
CH₂CF_Three           CH₂S (O)₂Me
CH₂CN CH₂S (O)₂Me
CH₂C (O) OMe CH₂S (O)₂Me
CH₂C (O) Me CH₂S (O)₂Me
CH₂OMe CH₂S (O)₂Me
CH₂SMe CH₂S (O)₂Me
CH₂Ph CH₂S (O)₂Me
CH₂(D-105a) CH₂S (O)₂Me
CH₂OC (O) Me CH₂S (O)₂Me
SCCl_Three           CH₂S (O)₂Me
CH₂SiMe_Three         CH₂S (O)₂Me
CH₂C (NOMe) Me CH₂S (O)₂Me
H CH₂CH₂SMe
H CH₂CH₂S (O) Me
H CH₂CH₂S (O)₂Me
H CH (Me) CH₂SMe
Me CH (Me) CH₂SMe
Et CH (Me) CH₂SMe
n-Pr CH (Me) CH₂SMe
i-Pr CH (Me) CH₂SMe
c-Pen CH (Me) CH₂SMe
C (O) OMe CH (Me) CH₂SMe
C (O) Me CH (Me) CH₂SMe
C (O) CF_Three         CH (Me) CH₂SMe
C (O) NMe₂        CH (Me) CH₂SMe
SO₂Me CH (Me) CH₂SMe
S (O)₂CF_Three         CH (Me) CH₂SMe
CH₂CH = C (Cl)₂     CH (Me) CH₂SMe
CH₂CH = CH₂        CH (Me) CH₂SMe
CH₂C≡CH CH (Me) CH₂SMe
CH₂Pr-c CH (Me) CH₂SMe
CH₂CF_Three           CH (Me) CH₂SMe
CH₂CN CH (Me) CH₂SMe
CH₂C (O) OMe CH (Me) CH₂SMe
CH₂C (O) Me CH (Me) CH₂SMe
CH₂OMe CH (Me) CH₂SMe
CH₂SMe CH (Me) CH₂SMe
CH₂Ph CH (Me) CH₂SMe
CH₂(D-105a) CH (Me) CH₂SMe
CH₂OC (O) Me CH (Me) CH₂SMe
SCCl_Three           CH (Me) CH₂SMe
CH₂SiMe_Three        CH (Me) CH₂SMe
CH₂C (NOMe) Me CH (Me) CH₂SMe
H CH (Me) CH₂S (O) Me
Me CH (Me) CH₂S (O) Me
Et CH (Me) CH₂S (O) Me
n-Pr CH (Me) CH₂S (O) Me
i-Pr CH (Me) CH₂S (O) Me
c-Pen CH (Me) CH₂S (O) Me
C (O) OMe CH (Me) CH₂S (O) Me
C (O) Me CH (Me) CH₂S (O) Me
C (O) CF_Three         CH (Me) CH₂S (O) Me
C (O) NMe₂        CH (Me) CH₂S (O) Me
SO₂Me CH (Me) CH₂S (O) Me
S (O)₂CF_Three         CH (Me) CH₂S (O) Me
CH₂CH = C (Cl)₂     CH (Me) CH₂S (O) Me
CH₂CH = CH₂        CH (Me) CH₂S (O) Me
CH₂C≡CH CH (Me) CH₂S (O) Me
CH₂Pr-c CH (Me) CH₂S (O) Me
CH₂CF_Three           CH (Me) CH₂S (O) Me
CH₂CN CH (Me) CH₂S (O) Me
CH₂C (O) OMe CH (Me) CH₂S (O) Me
CH₂C (O) Me CH (Me) CH₂S (O) Me
CH₂OMe CH (Me) CH₂S (O) Me
CH₂SMe CH (Me) CH₂S (O) Me
CH₂Ph CH (Me) CH₂S (O) Me
CH₂(D-105a) CH (Me) CH₂S (O) Me
CH₂OC (O) Me CH (Me) CH₂S (O) Me
SCCl_Three           CH (Me) CH₂S (O) Me
CH₂SiMe_Three        CH (Me) CH₂S (O) Me
CH₂C (NOMe) Me CH (Me) CH₂S (O) Me
H CH (Me) CH₂S (O)₂Me
Me CH (Me) CH₂S (O)₂Me
Et CH (Me) CH₂S (O)₂Me
n-Pr CH (Me) CH₂S (O)₂Me
i-Pr CH (Me) CH₂S (O)₂Me
c-Pen CH (Me) CH₂S (O)₂Me
C (O) OMe CH (Me) CH₂S (O)₂Me
C (O) Me CH (Me) CH₂S (O)₂Me
C (O) CF_Three         CH (Me) CH₂S (O)₂Me
C (O) NMe₂        CH (Me) CH₂S (O)₂Me
SO₂Me CH (Me) CH₂S (O)₂Me
S (O)₂CF_Three         CH (Me) CH₂S (O)₂Me
CH₂CH = C (Cl)₂     CH (Me) CH₂S (O)₂Me
CH₂CH = CH₂        CH (Me) CH₂S (O)₂Me
CH₂C≡CH CH (Me) CH₂S (O)₂Me
CH₂Pr-c CH (Me) CH₂S (O)₂Me
CH₂CF_Three           CH (Me) CH₂S (O)₂Me
CH₂CN CH (Me) CH₂S (O)₂Me
CH₂C (O) OMe CH (Me) CH₂S (O)₂Me
CH₂C (O) Me CH (Me) CH₂S (O)₂Me
CH₂OMe CH (Me) CH₂S (O)₂Me
CH₂SMe CH (Me) CH₂S (O)₂Me
CH₂Ph CH (Me) CH₂S (O)₂Me
CH₂(D-105a) CH (Me) CH₂S (O)₂Me
CH₂OC (O) Me CH (Me) CH₂S (O)₂Me
SCCl_Three           CH (Me) CH₂S (O)₂Me
CH₂SiMe_Three         CH (Me) CH₂S (O)₂Me
CH₂C (NOMe) Me CH (Me) CH₂S (O)₂Me
H CH₂CH (Me) SMe
Me CH₂CH (Me) SMe
Et CH₂CH (Me) SMe
n-Pr CH₂CH (Me) SMe
i-Pr CH₂CH (Me) SMe
c-Pen CH₂CH (Me) SMe
C (O) OMe CH₂CH (Me) SMe
C (O) Me CH₂CH (Me) SMe
C (O) CF_Three         CH₂CH (Me) SMe
C (O) NMe₂        CH₂CH (Me) SMe
SO₂Me CH₂CH (Me) SMe
S (O)₂CF_Three         CH₂CH (Me) SMe
CH₂CH = C (Cl)₂     CH₂CH (Me) SMe
CH₂CH = CH₂        CH₂CH (Me) SMe
CH₂C≡CH CH₂CH (Me) SMe
CH₂Pr-c CH₂CH (Me) SMe
CH₂CF_Three           CH₂CH (Me) SMe
CH₂CN CH₂CH (Me) SMe
CH₂C (O) OMe CH₂CH (Me) SMe
CH₂C (O) Me CH₂CH (Me) SMe
CH₂OMe CH₂CH (Me) SMe
CH₂SMe CH₂CH (Me) SMe
CH₂Ph CH₂CH (Me) SMe
CH₂(D-105a) CH₂CH (Me) SMe
CH₂OC (O) Me CH₂CH (Me) SMe
SCCl_Three           CH₂CH (Me) SMe
CH₂SiMe_Three         CH₂CH (Me) SMe
CH₂C (NOMe) Me CH₂CH (Me) SMe
H CH₂CH (Me) S (O) Me
Me CH₂CH (Me) S (O) Me
Et CH₂CH (Me) S (O) Me
n-Pr CH₂CH (Me) S (O) Me
i-Pr CH₂CH (Me) S (O) Me
c-Pen CH₂CH (Me) S (O) Me
C (O) OMe CH₂CH (Me) S (O) Me
C (O) Me CH₂CH (Me) S (O) Me
C (O) CF_Three         CH₂CH (Me) S (O) Me
C (O) NMe₂        CH₂CH (Me) S (O) Me
SO₂Me CH₂CH (Me) S (O) Me
S (O)₂CF_Three         CH₂CH (Me) S (O) Me
CH₂CH = C (Cl)₂     CH₂CH (Me) S (O) Me
CH₂CH = CH₂        CH₂CH (Me) S (O) Me
CH₂C≡CH CH₂CH (Me) S (O) Me
CH₂Pr-c CH₂CH (Me) S (O) Me
CH₂CF_Three           CH₂CH (Me) S (O) Me
CH₂CN CH₂CH (Me) S (O) Me
CH₂C (O) OMe CH₂CH (Me) S (O) Me
CH₂C (O) Me CH₂CH (Me) S (O) Me
CH₂OMe CH₂CH (Me) S (O) Me
CH₂SMe CH₂CH (Me) S (O) Me
CH₂Ph CH₂CH (Me) S (O) Me
CH₂(D-105a) CH₂CH (Me) S (O) Me
CH₂OC (O) Me CH₂CH (Me) S (O) Me
SCCl_Three           CH₂CH (Me) S (O) Me
CH₂SiMe_Three         CH₂CH (Me) S (O) Me
CH₂C (NOMe) Me CH₂CH (Me) S (O) Me
H CH₂CH (Me) S (O)₂Me
Me CH₂CH (Me) S (O)₂Me
Et CH₂CH (Me) S (O)₂Me
n-Pr CH₂CH (Me) S (O)₂Me
i-Pr CH₂CH (Me) S (O)₂Me
c-Pen CH₂CH (Me) S (O)₂Me
C (O) OMe CH₂CH (Me) S (O)₂Me
C (O) Me CH₂CH (Me) S (O)₂Me
C (O) CF_Three         CH₂CH (Me) S (O)₂Me
C (O) NMe₂        CH₂CH (Me) S (O)₂Me
SO₂Me CH₂CH (Me) S (O)₂Me
S (O)₂CF_Three         CH₂CH (Me) S (O)₂Me
CH₂CH = C (Cl)₂     CH₂CH (Me) S (O)₂Me
CH₂CH = CH₂        CH₂CH (Me) S (O)₂Me
CH₂C≡CH CH₂CH (Me) S (O)₂Me
CH₂Pr-c CH₂CH (Me) S (O)₂Me
CH₂CF_Three           CH₂CH (Me) S (O)₂Me
CH₂CN CH₂CH (Me) S (O)₂Me
CH₂C (O) OMe CH₂CH (Me) S (O)₂Me
CH₂C (O) Me CH₂CH (Me) S (O)₂Me
CH₂OMe CH₂CH (Me) S (O)₂Me
CH₂SMe CH₂CH (Me) S (O)₂Me
CH₂Ph CH₂CH (Me) S (O)₂Me
CH₂(D-105a) CH₂CH (Me) S (O)₂Me
CH₂OC (O) Me CH₂CH (Me) S (O)₂Me
SCCl_Three           CH₂CH (Me) S (O)₂Me
CH₂SiMe_Three         CH₂CH (Me) S (O)₂Me
CH₂C (NOMe) Me CH₂CH (Me) S (O)₂Me
H CH (Me) CH (Me) SMe
Me CH (Me) CH (Me) SMe
Et CH (Me) CH (Me) SMe
n-Pr CH (Me) CH (Me) SMe
i-Pr CH (Me) CH (Me) SMe
c-Pen CH (Me) CH (Me) SMe
C (O) OMe CH (Me) CH (Me) SMe
C (O) Me CH (Me) CH (Me) SMe
C (O) CF_Three         CH (Me) CH (Me) SMe
C (O) NMe₂        CH (Me) CH (Me) SMe
SO₂Me CH (Me) CH (Me) SMe
S (O)₂CF_Three         CH (Me) CH (Me) SMe
CH₂CH = C (Cl)₂     CH (Me) CH (Me) SMe
CH₂CH = CH₂        CH (Me) CH (Me) SMe
CH₂C≡CH CH (Me) CH (Me) SMe
CH₂Pr-c CH (Me) CH (Me) SMe
CH₂CF_Three           CH (Me) CH (Me) SMe
CH₂CN CH (Me) CH (Me) SMe
CH₂C (O) OMe CH (Me) CH (Me) SMe
CH₂C (O) Me CH (Me) CH (Me) SMe
CH₂OMe CH (Me) CH (Me) SMe
CH₂SMe CH (Me) CH (Me) SMe
CH₂Ph CH (Me) CH (Me) SMe
CH₂(D-105a) CH (Me) CH (Me) SMe
CH₂OC (O) Me CH (Me) CH (Me) SMe
SCCl_Three           CH (Me) CH (Me) SMe
CH₂SiMe_Three         CH (Me) CH (Me) SMe
CH₂C (NOMe) Me CH (Me) CH (Me) SMe
H CH (Me) CH (Me) S (O) Me
Me CH (Me) CH (Me) S (O) Me
Et CH (Me) CH (Me) S (O) Me
n-Pr CH (Me) CH (Me) S (O) Me
i-Pr CH (Me) CH (Me) S (O) Me
c-Pen CH (Me) CH (Me) S (O) Me
C (O) OMe CH (Me) CH (Me) S (O) Me
C (O) Me CH (Me) CH (Me) S (O) Me
C (O) CF_Three         CH (Me) CH (Me) S (O) Me
C (O) NMe₂        CH (Me) CH (Me) S (O) Me
SO₂Me CH (Me) CH (Me) S (O) Me
S (O)₂CF_Three         CH (Me) CH (Me) S (O) Me
CH₂CH = C (Cl)₂     CH (Me) CH (Me) S (O) Me
CH₂CH = CH₂        CH (Me) CH (Me) S (O) Me
CH₂C≡CH CH (Me) CH (Me) S (O) Me
CH₂Pr-c CH (Me) CH (Me) S (O) Me
CH₂CF_Three           CH (Me) CH (Me) S (O) Me
CH₂CN CH (Me) CH (Me) S (O) Me
CH₂C (O) OMe CH (Me) CH (Me) S (O) Me
CH₂C (O) Me CH (Me) CH (Me) S (O) Me
CH₂OMe CH (Me) CH (Me) S (O) Me
CH₂SMe CH (Me) CH (Me) S (O) Me
CH₂Ph CH (Me) CH (Me) S (O) Me
CH₂(D-105a) CH (Me) CH (Me) S (O) Me
CH₂OC (O) Me CH (Me) CH (Me) S (O) Me
SCCl_Three           CH (Me) CH (Me) S (O) Me
CH₂SiMe_Three         CH (Me) CH (Me) S (O) Me
CH₂C (NOMe) Me CH (Me) CH (Me) S (O) Me
H CH (Me) CH (Me) S (O)₂Me
Me CH (Me) CH (Me) S (O)₂Me
Et CH (Me) CH (Me) S (O)₂Me
n-Pr CH (Me) CH (Me) S (O)₂Me
i-Pr CH (Me) CH (Me) S (O)₂Me
c-Pen CH (Me) CH (Me) S (O)₂Me
C (O) OMe CH (Me) CH (Me) S (O)₂Me
C (O) Me CH (Me) CH (Me) S (O)₂Me
C (O) CF_Three         CH (Me) CH (Me) S (O)₂Me
C (O) NMe₂        CH (Me) CH (Me) S (O)₂Me
SO₂Me CH (Me) CH (Me) S (O)₂Me
S (O)₂CF_Three         CH (Me) CH (Me) S (O)₂Me
CH₂CH = C (Cl)₂     CH (Me) CH (Me) S (O)₂Me
CH₂CH = CH₂        CH (Me) CH (Me) S (O)₂Me
CH₂C≡CH CH (Me) CH (Me) S (O)₂Me
CH₂Pr-c CH (Me) CH (Me) S (O)₂Me
CH₂CF_Three           CH (Me) CH (Me) S (O)₂Me
CH₂CN CH (Me) CH (Me) S (O)₂Me
CH₂C (O) OMe CH (Me) CH (Me) S (O)₂Me
CH₂C (O) Me CH (Me) CH (Me) S (O)₂Me
CH₂OMe CH (Me) CH (Me) S (O)₂Me
CH₂SMe CH (Me) CH (Me) S (O)₂Me
CH₂Ph CH (Me) CH (Me) S (O)₂Me
CH₂(D-105a) CH (Me) CH (Me) S (O)₂Me
CH₂OC (O) Me CH (Me) CH (Me) S (O)₂Me
SCCl_Three           CH (Me) CH (Me) S (O)₂Me
CH₂SiMe_Three         CH (Me) CH (Me) S (O)₂Me
CH₂C (NOMe) Me CH (Me) CH (Me) S (O)₂Me
H SEt
H S (O) Et
H S (O)₂Et
H CH₂CF_Three
H CH₂CN
H CH₂SEt
Me CH₂SEt
Et CH₂SEt
n-Pr CH₂SEt
i-Pr CH₂SEt
c-Pen CH₂SEt
C (O) OMe CH₂SEt
C (O) Me CH₂SEt
C (O) CF_Three         CH₂SEt
C (O) NMe₂        CH₂SEt
SO₂Me CH₂SEt
S (O)₂CF_Three         CH₂SEt
CH₂CH = C (Cl)₂     CH₂SEt
CH₂CH = CH₂        CH₂SEt
CH₂C≡CH CH₂SEt
CH₂Pr-c CH₂SEt
CH₂CF_Three           CH₂SEt
CH₂CN CH₂SEt
CH₂C (O) OMe CH₂SEt
CH₂C (O) Me CH₂SEt
CH₂OMe CH₂SEt
CH₂SMe CH₂SEt
CH₂Ph CH₂SEt
CH₂(D-105a) CH₂SEt
CH₂OC (O) Me CH₂SEt
SCCl_Three           CH₂SEt
CH₂SiMe_Three         CH₂SEt
CH₂C (NOMe) Me CH₂SEt
H CH₂S (O) Et
H CH₂S (O) Et
Me CH₂S (O) Et
Et CH₂S (O) Et
n-Pr CH₂S (O) Et
i-Pr CH₂S (O) Et
c-Pen CH₂S (O) Et
C (O) OMe CH₂S (O) Et
C (O) Me CH₂S (O) Et
C (O) CF_Three         CH₂S (O) Et
C (O) NMe₂        CH₂S (O) Et
SO₂Me CH₂S (O) Et
S (O)₂CF_Three         CH₂S (O) Et
CH₂CH = C (Cl)₂     CH₂S (O) Et
CH₂CH = CH₂        CH₂S (O) Et
CH₂C≡CH CH₂S (O) Et
CH₂Pr-c CH₂S (O) Et
CH₂CF_Three           CH₂S (O) Et
CH₂CN CH₂S (O) Et
CH₂C (O) OMe CH₂S (O) Et
CH₂C (O) Me CH₂S (O) Et
CH₂OMe CH₂S (O) Et
CH₂SMe CH₂S (O) Et
CH₂Ph CH₂S (O) Et
CH₂(D-105a) CH₂S (O) Et
CH₂OC (O) Me CH₂S (O) Et
SCCl_Three           CH₂S (O) Et
CH₂SiMe_Three         CH₂S (O) Et
CH₂C (NOMe) Me CH₂S (O) Et
H CH₂S (O)₂Et
Me CH₂S (O)₂Et
Et CH₂S (O)₂Et
n-Pr CH₂S (O)₂Et
i-Pr CH₂S (O)₂Et
c-Pen CH₂S (O)₂Et
C (O) OMe CH₂S (O)₂Et
C (O) Me CH₂S (O)₂Et
C (O) CF_Three         CH₂S (O)₂Et
C (O) NMe₂        CH₂S (O)₂Et
SO₂Me CH₂S (O)₂Et
S (O)₂CF_Three         CH₂S (O)₂Et
CH₂CH = C (Cl)₂     CH₂S (O)₂Et
CH₂CH = CH₂        CH₂S (O)₂Et
CH₂C≡CH CH₂S (O)₂Et
CH₂Pr-c CH₂S (O)₂Et
CH₂CF_Three           CH₂S (O)₂Et
CH₂CN CH₂S (O)₂Et
CH₂C (O) OMe CH₂S (O)₂Et
CH₂C (O) Me CH₂S (O)₂Et
CH₂OMe CH₂S (O)₂Et
CH₂SMe CH₂S (O)₂Et
CH₂Ph CH₂S (O)₂Et
CH₂(D-105a) CH₂S (O)₂Et
CH₂OC (O) Me CH₂S (O)₂Et
SCCl_Three           CH₂S (O)₂Et
CH₂SiMe_Three         CH₂S (O)₂Et
CH₂C (NOMe) Me CH₂S (O)₂Et
H CH₂CH₂SEt
H CH₂CH₂S (O) Et
H CH₂CH₂S (O)₂Et
H CH (Me) CH₂SEt
Me CH (Me) CH₂SEt
Et CH (Me) CH₂SEt
n-Pr CH (Me) CH₂SEt
i-Pr CH (Me) CH₂SEt
c-Pen CH (Me) CH₂SEt
C (O) OMe CH (Me) CH₂SEt
C (O) Me CH (Me) CH₂SEt
C (O) CF_Three         CH (Me) CH₂SEt
C (O) NMe₂        CH (Me) CH₂SEt
SO₂Me CH (Me) CH₂SEt
S (O)₂CF_Three         CH (Me) CH₂SEt
CH₂CH = C (Cl)₂     CH (Me) CH₂SEt
CH₂CH = CH₂        CH (Me) CH₂SEt
CH₂C≡CH CH (Me) CH₂SEt
CH₂Pr-c CH (Me) CH₂SEt
CH₂CF_Three           CH (Me) CH₂SEt
CH₂CN CH (Me) CH₂SEt
CH₂C (O) OMe CH (Me) CH₂SEt
CH₂C (O) Me CH (Me) CH₂SEt
CH₂OMe CH (Me) CH₂SEt
CH₂SMe CH (Me) CH₂SEt
CH₂Ph CH (Me) CH₂SEt
CH₂(D-105a) CH (Me) CH₂SEt
CH₂OC (O) Me CH (Me) CH₂SEt
SCCl_Three           CH (Me) CH₂SEt
CH₂SiMe_Three        CH (Me) CH₂SEt
CH₂C (NOMe) Me CH (Me) CH₂SEt
H CH (Me) CH₂S (O) Et
Me CH (Me) CH₂S (O) Et
Et CH (Me) CH₂S (O) Et
n-Pr CH (Me) CH₂S (O) Et
i-Pr CH (Me) CH₂S (O) Et
c-Pen CH (Me) CH₂S (O) Et
C (O) OMe CH (Me) CH₂S (O) Et
C (O) Me CH (Me) CH₂S (O) Et
C (O) CF_Three         CH (Me) CH₂S (O) Et
C (O) NMe₂        CH (Me) CH₂S (O) Et
SO₂Me CH (Me) CH₂S (O) Et
S (O)₂CF_Three         CH (Me) CH₂S (O) Et
CH₂CH = C (Cl)₂     CH (Me) CH₂S (O) Et
CH₂CH = CH₂        CH (Me) CH₂S (O) Et
CH₂C≡CH CH (Me) CH₂S (O) Et
CH₂Pr-c CH (Me) CH₂S (O) Et
CH₂CF_Three           CH (Me) CH₂S (O) Et
CH₂CN CH (Me) CH₂S (O) Et
CH₂C (O) OMe CH (Me) CH₂S (O) Et
CH₂C (O) Me CH (Me) CH₂S (O) Et
CH₂OMe CH (Me) CH₂S (O) Et
CH₂SMe CH (Me) CH₂S (O) Et
CH₂Ph CH (Me) CH₂S (O) Et
CH₂(D-105a) CH (Me) CH₂S (O) Et
CH₂OC (O) Me CH (Me) CH₂S (O) Et
SCCl_Three           CH (Me) CH₂S (O) Et
CH₂SiMe_Three        CH (Me) CH₂S (O) Et
CH₂C (NOMe) Me CH (Me) CH₂S (O) Et
H CH (Me) CH₂S (O)₂Et
Me CH (Me) CH₂S (O)₂Et
Et CH (Me) CH₂S (O)₂Et
n-Pr CH (Me) CH₂S (O)₂Et
i-Pr CH (Me) CH₂S (O)₂Et
c-Pen CH (Me) CH₂S (O)₂Et
C (O) OMe CH (Me) CH₂S (O)₂Et
C (O) Me CH (Me) CH₂S (O)₂Et
C (O) CF_Three         CH (Me) CH₂S (O)₂Et
C (O) NMe₂        CH (Me) CH₂S (O)₂Et
SO₂Me CH (Me) CH₂S (O)₂Et
S (O)₂CF_Three         CH (Me) CH₂S (O)₂Et
CH₂CH = C (Cl)₂     CH (Me) CH₂S (O)₂Et
CH₂CH = CH₂        CH (Me) CH₂S (O)₂Et
CH₂C≡CH CH (Me) CH₂S (O)₂Et
CH₂Pr-c CH (Me) CH₂S (O)₂Et
CH₂CF_Three           CH (Me) CH₂S (O)₂Et
CH₂CN CH (Me) CH₂S (O)₂Et
CH₂C (O) OMe CH (Me) CH₂S (O)₂Et
CH₂C (O) Me CH (Me) CH₂S (O)₂Et
CH₂OMe CH (Me) CH₂S (O)₂Et
CH₂SMe CH (Me) CH₂S (O)₂Et
CH₂Ph CH (Me) CH₂S (O)₂Et
CH₂(D-105a) CH (Me) CH₂S (O)₂Et
CH₂OC (O) Me CH (Me) CH₂S (O)₂Et
SCCl_Three           CH (Me) CH₂S (O)₂Et
CH₂SiMe_Three         CH (Me) CH₂S (O)₂Et
CH₂C (NOMe) Me CH (Me) CH₂S (O)₂Et
H CH₂CH (Me) SEt
Me CH₂CH (Me) SEt
Et CH₂CH (Me) SEt
n-Pr CH₂CH (Me) SEt
i-Pr CH₂CH (Me) SEt
c-Pen CH₂CH (Me) SEt
C (O) OMe CH₂CH (Me) SEt
C (O) Me CH₂CH (Me) SEt
C (O) CF_Three         CH₂CH (Me) SEt
C (O) NMe₂        CH₂CH (Me) SEt
SO₂Me CH₂CH (Me) SEt
S (O)₂CF_Three         CH₂CH (Me) SEt
CH₂CH = C (Cl)₂     CH₂CH (Me) SEt
CH₂CH = CH₂        CH₂CH (Me) SEt
CH₂C≡CH CH₂CH (Me) SEt
CH₂Pr-c CH₂CH (Me) SEt
CH₂CF_Three           CH₂CH (Me) SEt
CH₂CN CH₂CH (Me) SEt
CH₂C (O) OMe CH₂CH (Me) SEt
CH₂C (O) Me CH₂CH (Me) SEt
CH₂OMe CH₂CH (Me) SEt
CH₂SMe CH₂CH (Me) SEt
CH₂Ph CH₂CH (Me) SEt
CH₂(D-105a) CH₂CH (Me) SEt
CH₂OC (O) Me CH₂CH (Me) SEt
SCCl_Three           CH₂CH (Me) SEt
CH₂SiMe_Three         CH₂CH (Me) SEt
CH₂C (NOMe) Me CH₂CH (Me) SEt
H CH₂CH (Me) S (O) Et
Me CH₂CH (Me) S (O) Et
Et CH₂CH (Me) S (O) Et
n-Pr CH₂CH (Me) S (O) Et
i-Pr CH₂CH (Me) S (O) Et
c-Pen CH₂CH (Me) S (O) Et
C (O) OMe CH₂CH (Me) S (O) Et
C (O) Me CH₂CH (Me) S (O) Et
C (O) CF_Three         CH₂CH (Me) S (O) Et
C (O) NMe₂        CH₂CH (Me) S (O) Et
SO₂Me CH₂CH (Me) S (O) Et
S (O)₂CF_Three         CH₂CH (Me) S (O) Et
CH₂CH = C (Cl)₂     CH₂CH (Me) S (O) Et
CH₂CH = CH₂        CH₂CH (Me) S (O) Et
CH₂C≡CH CH₂CH (Me) S (O) Et
CH₂Pr-c CH₂CH (Me) S (O) Et
CH₂CF_Three           CH₂CH (Me) S (O) Et
CH₂CN CH₂CH (Me) S (O) Et
CH₂C (O) OMe CH₂CH (Me) S (O) Et
CH₂C (O) Me CH₂CH (Me) S (O) Et
CH₂OMe CH₂CH (Me) S (O) Et
CH₂SMe CH₂CH (Me) S (O) Et
CH₂Ph CH₂CH (Me) S (O) Et
CH₂(D-105a) CH₂CH (Me) S (O) Et
CH₂OC (O) Me CH₂CH (Me) S (O) Et
SCCl_Three           CH₂CH (Me) S (O) Et
CH₂SiMe_Three         CH₂CH (Me) S (O) Et
CH₂C (NOMe) Me CH₂CH (Me) S (O) Et
H CH₂CH (Me) S (O)₂Et
Me CH₂CH (Me) S (O)₂Et
Et CH₂CH (Me) S (O)₂Et
n-Pr CH₂CH (Me) S (O)₂Et
i-Pr CH₂CH (Me) S (O)₂Et
c-Pen CH₂CH (Me) S (O)₂Et
C (O) OMe CH₂CH (Me) S (O)₂Et
C (O) Me CH₂CH (Me) S (O)₂Et
C (O) CF_Three         CH₂CH (Me) S (O)₂Et
C (O) NMe₂        CH₂CH (Me) S (O)₂Et
SO₂Me CH₂CH (Me) S (O)₂Et
S (O)₂CF_Three         CH₂CH (Me) S (O)₂Et
CH₂CH = C (Cl)₂     CH₂CH (Me) S (O)₂Et
CH₂CH = CH₂        CH₂CH (Me) S (O)₂Et
CH₂C≡CH CH₂CH (Me) S (O)₂Et
CH₂Pr-c CH₂CH (Me) S (O)₂Et
CH₂CF_Three           CH₂CH (Me) S (O)₂Et
CH₂CN CH₂CH (Me) S (O)₂Et
CH₂C (O) OMe CH₂CH (Me) S (O)₂Et
CH₂C (O) Me CH₂CH (Me) S (O)₂Et
CH₂OMe CH₂CH (Me) S (O)₂Et
CH₂SMe CH₂CH (Me) S (O)₂Et
CH₂Ph CH₂CH (Me) S (O)₂Et
CH₂(D-105a) CH₂CH (Me) S (O)₂Et
CH₂OC (O) Me CH₂CH (Me) S (O)₂Et
SCCl_Three           CH₂CH (Me) S (O)₂Et
CH₂SiMe_Three         CH₂CH (Me) S (O)₂Et
CH₂C (NOMe) Me CH₂CH (Me) S (O)₂Et
H CH (Me) CH (Me) SEt
Me CH (Me) CH (Me) SEt
Et CH (Me) CH (Me) SEt
n-Pr CH (Me) CH (Me) SEt
i-Pr CH (Me) CH (Me) SEt
c-Pen CH (Me) CH (Me) SEt
C (O) OMe CH (Me) CH (Me) SEt
C (O) Me CH (Me) CH (Me) SEt
C (O) CF_Three         CH (Me) CH (Me) SEt
C (O) NMe₂        CH (Me) CH (Me) SEt
SO₂Me CH (Me) CH (Me) SEt
S (O)₂CF_Three         CH (Me) CH (Me) SEt
CH₂CH = C (Cl)₂     CH (Me) CH (Me) SEt
CH₂CH = CH₂        CH (Me) CH (Me) SEt
CH₂C≡CH CH (Me) CH (Me) SEt
CH₂Pr-c CH (Me) CH (Me) SEt
CH₂CF_Three           CH (Me) CH (Me) SEt
CH₂CN CH (Me) CH (Me) SEt
CH₂C (O) OMe CH (Me) CH (Me) SEt
CH₂C (O) Me CH (Me) CH (Me) SEt
CH₂OMe CH (Me) CH (Me) SEt
CH₂SMe CH (Me) CH (Me) SEt
CH₂Ph CH (Me) CH (Me) SEt
CH₂(D-105a) CH (Me) CH (Me) SEt
CH₂OC (O) Me CH (Me) CH (Me) SEt
SCCl_Three           CH (Me) CH (Me) SEt
CH₂SiMe_Three         CH (Me) CH (Me) SEt
CH₂C (NOMe) Me CH (Me) CH (Me) SEt
H CH (Me) CH (Me) S (O) Et
Me CH (Me) CH (Me) S (O) Et
Et CH (Me) CH (Me) S (O) Et
n-Pr CH (Me) CH (Me) S (O) Et
i-Pr CH (Me) CH (Me) S (O) Et
c-Pen CH (Me) CH (Me) S (O) Et
C (O) OMe CH (Me) CH (Me) S (O) Et
C (O) Me CH (Me) CH (Me) S (O) Et
C (O) CF_Three         CH (Me) CH (Me) S (O) Et
C (O) NMe₂        CH (Me) CH (Me) S (O) Et
SO₂Me CH (Me) CH (Me) S (O) Et
S (O)₂CF_Three         CH (Me) CH (Me) S (O) Et
CH₂CH = C (Cl)₂     CH (Me) CH (Me) S (O) Et
CH₂CH = CH₂        CH (Me) CH (Me) S (O) Et
CH₂C≡CH CH (Me) CH (Me) S (O) Et
CH₂Pr-c CH (Me) CH (Me) S (O) Et
CH₂CF_Three           CH (Me) CH (Me) S (O) Et
CH₂CN CH (Me) CH (Me) S (O) Et
CH₂C (O) OMe CH (Me) CH (Me) S (O) Et
CH₂C (O) Me CH (Me) CH (Me) S (O) Et
CH₂OMe CH (Me) CH (Me) S (O) Et
CH₂SMe CH (Me) CH (Me) S (O) Et
CH₂Ph CH (Me) CH (Me) S (O) Et
CH₂(D-105a) CH (Me) CH (Me) S (O) Et
CH₂OC (O) Me CH (Me) CH (Me) S (O) Et
SCCl_Three           CH (Me) CH (Me) S (O) Et
CH₂SiMe_Three         CH (Me) CH (Me) S (O) Et
CH₂C (NOMe) Me CH (Me) CH (Me) S (O) Et
H CH (Me) CH (Me) S (O)₂Et
Me CH (Me) CH (Me) S (O)₂Et
Et CH (Me) CH (Me) S (O)₂Et
n-Pr CH (Me) CH (Me) S (O)₂Et
i-Pr CH (Me) CH (Me) S (O)₂Et
c-Pen CH (Me) CH (Me) S (O)₂Et
C (O) OMe CH (Me) CH (Me) S (O)₂Et
C (O) Me CH (Me) CH (Me) S (O)₂Et
C (O) CF_Three         CH (Me) CH (Me) S (O)₂Et
C (O) NMe₂        CH (Me) CH (Me) S (O)₂Et
SO₂Me CH (Me) CH (Me) S (O)₂Et
S (O)₂CF_Three         CH (Me) CH (Me) S (O)₂Et
CH₂CH = C (Cl)₂     CH (Me) CH (Me) S (O)₂Et
CH₂CH = CH₂        CH (Me) CH (Me) S (O)₂Et
CH₂C≡CH CH (Me) CH (Me) S (O)₂Et
CH₂Pr-c CH (Me) CH (Me) S (O)₂Et
CH₂CF_Three           CH (Me) CH (Me) S (O)₂Et
CH₂CN CH (Me) CH (Me) S (O)₂Et
CH₂C (O) OMe CH (Me) CH (Me) S (O)₂Et
CH₂C (O) Me CH (Me) CH (Me) S (O)₂Et
CH₂OMe CH (Me) CH (Me) S (O)₂Et
CH₂SMe CH (Me) CH (Me) S (O)₂Et
CH₂Ph CH (Me) CH (Me) S (O)₂Et
CH₂(D-105a) CH (Me) CH (Me) S (O)₂Et
CH₂OC (O) Me CH (Me) CH (Me) S (O)₂Et
SCCl_Three           CH (Me) CH (Me) S (O)₂Et
CH₂SiMe_Three         CH (Me) CH (Me) S (O)₂Et
CH₂C (NOMe) Me CH (Me) CH (Me) S (O)₂Et
H CH₂CH (OMe)₂
H CH₂CH (OEt)₂
H NHC (O) OMe
H NHC (O) OEt
H NHC (O) OPr-n
H NHC (O) OPr-i
H NHC (O) OBu-n
H NHC (O) OBu-i
H NHC (O) OBu-s
H NHC (O) OBu-t
H D1-32a
H D1-33a
H D1-34a
H D1-37a
H CH₂(D1-32a)
H CH₂(D1-33a)
H CH₂(D1-34a)
H CH₂(D1-37a)
Me CH₂CF_Three
Me CH₂CH₂SMe
Me CH₂CH₂S (O) Me
Me CH₂CH₂S (O)₂Me
Me CH₂CH (OMe)₂
Me CH₂CH (OEt)₂
Me NHC (O) OMe
Me NHC (O) OEt
Me NHC (O) OPr-n
Me NHC (O) OPr-i
Me NHC (O) OBu-n
Me NHC (O) OBu-i
Me NHC (O) OBu-s
Me NHC (O) OBu-t
Me D1-32a
Me D1-33a
Me D1-34a
Me D1-37a
Me CH₂(D1-32a)
Me CH₂(D1-33a)
Me CH₂(D1-34a)
Me CH₂(D1-37a)
H H
H Me
H Et
H n-Pr
H i-Pr
H c-Pr
H n-Bu
H i-Bu
H s-Bu
H t-Bu
H c-Bu
H n-Pen
H c-Pen
H n-Hex
H c-Hex
H Hep
H Oct
H CH₂Pr-c
H CH₂Bu-i
H CH₂Bu-s
H CH₂Bu-t
H CH₂Bu-c
H CH₂Pen-c
H CH₂Hex-c
H CH (CH_ThreePr-n
H CH (CH_ThreePr-i
H CH (CH_ThreePr-n
H CH (CH_Three) Bu-i
H CH (Et)₂
H C (CH_Three)₂Et
H C (CH_Three)₂Pr-n
H CH₂CH₂F
H CH₂CH₂Cl
H CH₂CH₂Br
H CH₂CHF₂
H CH₂CHFCl
H CH₂CHCl₂
H CH₂CHFBr
H CH₂CF₂Cl
H CH₂CFCl₂
H CH₂CCl_Three
H CH₂CF₂Br
H CH₂CFClBr
H CH₂CCl₂Br
H CH (CH_Three) CH₂F
H CH (CH_Three) CH₂Cl
H CH (CH_Three) CH₂Br
H CH₂CHFCH_Three
H CH₂CHClCH_Three
H CH₂CHBrCH_Three
H CH₂CFClCH_Three
H CH₂CHClCH₂Cl
H CH₂CHBrCH₂F
H CH₂CHClCH₂Br
H CH₂CHBrCH₂Cl
H CH₂CHBrCHCl₂
H CH₂CClBrCH_Three
H CH₂CHBrCH₂Br
H CH₂CH₂CF_Three
H CH₂CH₂CF₂Br
H CH₂CClBrCH₂Cl
H CH₂CF₂CF₂H
H CH₂CHClCF_Three
H CH₂CF₂CF_Three
H CH₂CF (CH_Three)₂
H CH₂CHFCH₂CH_Three
H CH₂CHClCH₂CH_Three
H CH₂CF₂CHFCF_Three
H CH₂CF₂CF₂CHF₂
H CH₂CF₂CF₂CF_Three
H C (CH_Three)₂CH₂Cl
H C (CH_Three)₂CH₂Br
H C (CH_Three)₂CHBrCH₂Br
H CH₂CF_Three
Me CH₂CF_Three
Et CH₂CF_Three
n-Pr CH₂CF_Three
i-Pr CH₂CF_Three
CH₂OCH_Three          CH₂CF_Three
CH₂CH₂OEt CH₂CF_Three
CH₂SCH_Three          CH₂CF_Three
CH₂CN  CH₂CF_Three
CH₂CO₂Me CH₂CF_Three
CH₂CO₂Et CH₂CF_Three
CH₂CH = CH₂        CH₂CF_Three
CH₂CH≡CH CH₂CF_Three
C (O) CH_Three          CH₂CF_Three
C (O) Et CH₂CF_Three
C (O) Pr-n CH₂CF_Three
C (O) Pr-c CH₂CF_Three
C (O) Bu-t CH₂CF_Three
C (O) CH₂OCH_Three      CH₂CF_Three
C (O) CH₂SCH_Three      CH₂CF_Three
C (O) OMe CH₂CF_Three
C (O) OEt CH₂CF_Three
C (O) CH₂CH₂Cl CH₂CF_Three
C (O) CH₂CH₂OMe CH₂CF_Three
C (O) OCH₂CH = CH₂   CH₂CF_Three
C (O) SCH_Three         CH₂CF_Three
C (S) OCH_Three          CH₂CF_Three
C (S) SCH_Three         CH₂CF_Three
SMe CH₂CF_Three
SPh CH₂CF_Three
SNEt₂            CH₂CF_Three
SO₂Me CH₂CF_Three
SO₂Et CH₂CF_Three
SO₂Ph CH₂CF_Three
SO₂NMe₂          CH₂CF_Three
NH₂              CH₂CF_Three
NHMe CH₂CF_Three
NHCHO CH₂CF_Three
NHC (O) CH_Three        CH₂CF_Three
NHC (O) CF_Three        CH₂CF_Three
NHC (O) OCH_Three       CH₂CF_Three
N = C (CH_Three)₂        CH₂CF_Three
N = CHPh CH₂CF_Three
H CH (CF_Three) Me
H CH (CF_Three) Et
H CH (CF_Three) OH
H CH (CF_Three) OMe
H CH₂CH (OMe)₂
H CH₂CH (OEt)₂
H CH₂CN
H CH (Me) CN
H C (Me)₂CN
H CH (OMe) CN
H CH₂CH₂CN
H CH₂C (O) Me
H CH₂C (O) OMe
H CH₂C (O) OEt
H CH₂C (O) OCH₂CF_Three
H CH (Me) C (O) OMe
H CH (Me) C (O) OEt
H CH (Me) C (O) OCH₂CF_Three
H CH (OMe) C (O) OMe
H CH (OMe) C (O) OEt
H CH (OMe) C (O) OCH₂CF_Three
H CH (Ph) C (O) OMe
H CH (Ph) C (O) OEt
H CH (Ph) C (O) OCH₂CF_Three
H CH (CF_Three) C (O) OMe
H CH (CF_Three) C (O) OEt
H CH (CF_Three) C (O) OCH₂CF_Three
H CH₂CH₂C (O) OMe
H CH₂CH₂C (O) OEt
H CH₂CH₂C (O) OCH₂CF_Three
H CH₂CH (Me) C (O) OMe
H CH₂CH (Me) C (O) OEt
H CH (Me) CH₂C (O) OMe
H CH (Me) CH₂C (O) OEt
H CH₂C (O) NH₂
H CH₂C (O) NHMe
H CH₂C (O) NHEt
H CH₂C (O) NHPr-n
H CH₂C (O) NHPr-i
H CH₂C (O) NHPr-c
H CH₂C (O) NHBu-n
H CH₂C (O) NHBu-i
H CH₂C (O) NHBu-s
H CH₂C (O) NHBu-t
H CH₂C (O) NHBu-c
H CH₂C (O) NHHex-n
H CH₂C (O) NHHex-c
H CH₂C (O) N (Me)₂
H CH₂C (O) N (Et)₂
H CH₂C (O) N (n-Pr)₂
H CH₂C (O) N (Me) Et
H CH₂C (O) N (Me) Pr-n
H CH₂C (O) N (Me) Pr-i
H CH₂C (O) NHCH₂CH₂F
H CH₂C (O) NHCH₂CH₂Cl
H CH₂C (O) NHCH₂CH₂Br
H CH₂C (O) N (Me) CH₂CH₂F
H CH₂C (O) N (Me) CH₂CH₂Cl
H CH₂C (O) N (Me) CH₂CH₂Br
H CH₂C (O) NHCH₂CF_Three
CH₂OCH_Three          CH₂C (O) NHCH₂CF_Three
CH₂CN CH₂C (O) NHCH₂CF_Three
CH₂CO₂Me CH₂C (O) NHCH₂CF_Three
CH₂CO₂Et CH₂C (O) NHCH₂CF_Three
CH₂CH = CH₂        CH₂C (O) NHCH₂CF_Three
CH₂CH≡CH CH₂C (O) NHCH₂CF_Three
C (O) Me CH₂C (O) NHCH₂CF_Three
C (O) OMe CH₂C (O) NHCH₂CF_Three
H CH₂C (O) N (Me) CH₂CF_Three
H CH₂C (O) NHCH₂CF₂Cl
H CH₂C (O) NHCH₂CN
H CH₂C (O) NHCH₂CH = CH₂
H CH₂C (O) NHCH₂CH≡CH
H CH₂C (O) NHCH₂CH₂CH₂Cl
H CH₂C (O) NHCH₂CH₂OCH_Three
H CH₂C (O) NHCH₂CH₂SCH_Three
H CH₂C (O) NHCH₂CH₂SO₂CH_Three
H CH (Me) C (O) NH₂
H CH (Me) C (O) NHMe
H CH (Me) C (O) NHEt
H CH (Me) C (O) NHPr-n
H CH (Me) C (O) NHPr-i
H CH (Me) C (O) NHPr-c
H CH (Me) C (O) NHBu-n
H CH (Me) C (O) NHBu-i
H CH (Me) C (O) NHBu-s
H CH (Me) C (O) NHBu-t
H CH (Me) C (O) NHBu-c
H CH (Me) C (O) NHHex-n
H CH (Me) C (O) NHHex-c
H CH (Me) C (O) N (Me)₂
H CH (Me) C (O) N (Et)₂
H CH (Me) C (O) N (n-Pr)₂
H CH (Me) C (O) N (Me) Et
H CH (Me) C (O) N (Me) Pr-n
H CH (Me) C (O) N (Me) Pr-i
H CH (Me) C (O) NHCH₂CH₂F
H CH (Me) C (O) NHCH₂CH₂Cl
H CH (Me) C (O) NHCH₂CH₂Br
H CH (Me) C (O) NHCH₂CF_Three
H CH (Et) C (O) NHCH₂CF_Three
H CH (i-Pr) C (O) NHCH₂CF_Three
H CH (CH₂OCH_Three) C (O) NHCH₂CF_Three
H CH (CH₂SCH_Three) C (O) NHCH₂CF_Three
H CH (Ph) C (O) NHCH₂CF_Three
H CH (CH₂Ph) C (O) NHCH₂CF_Three
H CH (CF_Three) C (O) NHMe
H CH (CF_Three) C (O) NHEt
H CH (CF_Three) C (O) NHPr-n
H CH (CF_Three) C (O) NHPr-i
H CH (CF_Three) C (O) NHPr-c
H CH (CF_Three) C (O) NHBu-n
H CH (CF_Three) C (O) NHBu-i
H CH (CF_Three) C (O) NHBu-s
H CH (CF_Three) C (O) NHBu-t
H CH (CF_Three) C (O) NHBu-c
H CH (CF_Three) C (O) NHHex-n
H CH (CF_Three) C (O) NHHex-c
H CH (CF_Three) C (O) N (Me)₂
H CH (CF_Three) C (O) N (Et)₂
H CH (CF_Three) C (O) N (n-Pr)₂
H CH (CF_Three) C (O) N (Me) Et
H CH (CF_Three) C (O) N (Me) Pr-n
H CH (CF_Three) C (O) N (Me) Pr-i
H CH (CF_Three) C (O) NHCH₂CH₂F
H CH (CF_Three) C (O) NHCH₂CH₂Cl
H CH (CF_Three) C (O) NHCH₂CH₂Br
H CH (CF_Three) C (O) NHCH₂CF_Three
H CH₂CH₂C (O) NHCH₂CF_Three
H CH₂C (O) N (Me)₂
H CH₂C (O) N (Et)₂
H CH₂C (O) N (n-Pr)₂
H CH₂CH = CH₂
H CH₂C (Me) = CH₂
H CH₂C (Et) = CH₂
H CH (Me) CH = CH₂
H CH₂CH = C (Me)₂
H CH₂C (Me) = CHCH_Three
H CH (Me) CH = CHCH_Three
H CH₂C (F) = CH₂
H CH₂CH = CHCl
H CH₂C (Cl) = CH₂
H CH₂CH = CCl₂
H CH₂CH = CHBr
H CH₂C (Br) = CH₂
H CH₂C (Br) = CHBr
H CH₂C (Me) = CHBr
H CH₂CH = C (Cl) CH_Three
H CH₂CH = C (Br) CH_Three
H CH₂C (OMe) = CH₂
H CH₂C (Br) = CHOMe
H CH₂C (Br) = CHOEt
H CH₂C (Br) = CHPh
H CH₂C≡CH
H CH₂C≡CCl
H CH₂C≡CBr
H CH₂C≡CI
H CH₂C≡CPh
H CH₂OMe
H CH₂CH₂OH
H CH₂CH₂OMe
H CH₂CH₂OEt
H CH₂CH₂OPr-n
H CH₂CH₂OPr-i
H CH₂CH₂OBu-i
H CH₂CH₂OCH₂CH₂Cl
H CH₂CH₂OCH₂CF3
H CH₂CH₂OCH₂CH₂OCH_Three
H CH₂CH₂OCH₂CH₂SCH_Three
H CH₂CH₂OC (O) CH_Three
H CH₂CH (Me) OH
H CH₂CH (Me) OMe
H CH₂CH (Me) OCH₂CF_Three
H CH (Me) CH₂OH
H CH (Me) CH₂OMe
H CH (Me) CH₂OCH₂CF_Three
H CH (Ph) CH₂OH
H CH (Ph) CH₂OMe
H CH (Ph) CH₂OCH₂CF_Three
H C (Me)₂CH₂OH
H C (Me)₂CH₂OMe
H C (Me)₂CH₂OCH₂CF_Three
H CH₂CH₂CH₂OH
H CH₂CH₂CH₂OMe
H CH₂CH₂CH₂OCH₂CF_Three
H CH₂CH₂CH₂CH₂OH
H CH₂CH₂CH₂CH₂OMe
H CH₂CH₂CH₂CH₂OCH₂CF_Three
H CH₂SMe
H CH (CF_ThreeSMe
H CH (CF_Three) SEt
H CH₂CH₂SEt
H CH₂CH₂S (O) Et
H CH₂CH₂S (O)₂Et
H CH₂CH₂SPr-n
H CH₂CH₂S (O) Pr-n
H CH₂CH₂S (O)₂Pr-n
H CH₂CH₂SPr-i
H CH₂CH₂S (O) Pr-i
H CH₂CH₂S (O)₂Pr-i
H CH₂CH₂SCH₂CF_Three
H CH₂CH₂S (O) CH₂CF_Three
H CH₂CH₂S (O)₂CH₂CF_Three
H CH₂CH₂SCH₂CH₂OH
H CH₂CH₂S (O) CH₂CH₂OH
H CH₂CH₂S (O)₂CH₂CH₂OH
H CH₂CH₂SCH₂CH₂OMe
H CH₂CH₂S (O) CH₂CH₂OMe
H CH₂CH₂S (O)₂CH₂CH₂OMe
H CH₂CH₂SCH₂C (O) OMe
H CH₂CH₂S (O) CH₂C (O) OMe
H CH₂CH₂S (O)₂CH₂C (O) OMe
H CH₂CH₂SCH₂C (O) NHMe
H CH₂CH₂S (O) CH₂C (O) NHMe
H CH₂CH₂S (O)₂CH₂C (O) NHMe
H CH₂CH₂SCH₂C (O) NMe
H CH₂CH₂S (O) CH₂C (O) NMe
H CH₂CH₂S (O)₂CH₂C (O) N (Me)₂
H CH₂CH₂SCH₂CH = CH₂
H CH₂CH₂SCH₂CH≡CH
H CH₂CH₂S (O)₂NHMe
H CH₂CH₂S (O)₂N (Me)₂
H CH₂CH₂S (O)₂NHEt
H CH₂CH₂S (O)₂N (Et)₂
H CH₂CH₂S (O)₂NHPr-n
H CH₂CH₂S (O)₂N (Pr-n)₂
H CH₂CH₂S (O)₂NHPr-i
H CH₂CH₂S (O)₂N (Pr-i)₂
H CH₂CH₂S (O)₂NHPr-c
H CH₂CH₂S (O)₂NHBu-t
H CH₂CH₂S (O)₂NHCH₂CF_Three
H CH₂CH₂S (O)₂NHCH₂CH₂OMe
H CH₂CH₂S (O)₂NHCH₂CH₂SMe
H CH₂CH₂S (O)₂NHCH₂CH = CH₂
H CH₂CH₂S (O)₂NHCH₂CH≡CH
H CH₂CH₂S (O) (= NCN) Me
H CH₂CH (Et) SMe
H CH₂CH (Et) S (O) Me
H CH₂CH (Et) S (O)₂Me
H CH₂CH (n-Pr) SMe
H CH₂CH (n-Pr) S (O) Me
H CH₂CH (n-Pr) S (O)₂Me
H CH₂CH (i-Pr) SMe
H CH₂CH (i-Pr) S (O) Me
H CH₂CH (i-Pr) S (O)₂Me
H CH₂CH (Ph) SMe
H CH₂CH (Ph) S (O) Me
H CH₂CH (Ph) S (O)₂Me
H CH (Me) CH₂SPr-n
H CH (Me) CH₂S (O) Pr-n
H CH (Me) CH₂S (O)₂Pr-n
H CH (Me) CH₂SPr-i
H CH (Me) CH₂S (O) Pr-i
H CH (Me) CH₂S (O)₂Pr-i
H CH (Me) CH₂SPh
H CH (Me) CH₂S (O) Ph
H CH (Me) CH₂S (O)₂Ph
H CH (Ph) CH₂SMe
H CH (Ph) CH₂S (O) Me
H CH (Ph) CH₂S (O)₂Me
H C (Me)₂CH₂SMe
H C (Me)₂CH₂S (O) Me
H C (Me)₂CH₂S (O)₂Me
H CH₂CH₂CH₂SMe
H CH₂CH₂CH₂S (O) Me
H CH₂CH₂CH₂S (O)₂Me
H CH₂CH₂CH (Me) SMe
H CH₂CH₂CH (Me) S (O) Me
H CH₂CH₂CH (Me) S (O)₂Me
H CH₂CH (Me) CH₂SMe
H CH₂CH (Me) CH₂S (O) Me
H CH₂CH (Me) CH₂S (O)₂Me
H CH (Me) CH₂CH₂SMe
H CH (Me) CH₂CH₂S (O) Me
H CH (Me) CH₂CH₂S (O)₂Me
H C (Me)₂CH₂CH₂SMe
H C (Me)₂CH₂CH₂S (O) Me
H C (Me)₂CH₂CH₂S (O)₂Me
H CH (Me) (CH₂)_ThreeSMe
H CH (Me) (CH₂)_ThreeS (O) Me
H CH (Me) (CH₂)_ThreeS (O)₂Me
H CH (Me) (CH₂)_FourSMe
H CH (Me) (CH₂)_FourS (O) Me
H CH (Me) (CH₂)_FourS (O)₂Me
H CH₂NHC (O) Me
H CH₂NHC (O) Et
H CH₂NHC (O) Pr-n
H CH₂CH₂NHC (O) Me
H CH₂CH₂NHC (O) Et
H CH₂CH₂NHC (O) Pr-n
H CH₂CH₂NHC (O) Pr-i
H CH₂CH₂NHC (O) Pr-c
H CH₂CH₂NHC (O) Bu-n
H CH₂CH₂NHC (O) Bu-i
H CH₂CH₂NHC (O) Bu-s
H CH₂CH₂NHC (O) Bu-t
H CH₂CH₂NHC (O) CF_Three
H CH₂CH₂NHC (O) CF₂Cl
H CH₂CH₂NHC (O) Ph
H CH₂CH₂NHC (O) CH₂CF_Three
H CH₂CH₂NHC (O) CH₂SMe
H CH₂CH₂NHC (O) CH₂S (O) Me
H CH₂CH₂NHC (O) CH₂S (O)₂Me
H CH₂CH₂N (Me) C (O) Me
H CH₂CH₂N (Me) C (O) Et
H CH₂CH₂N (Me) C (O) CF_Three
H CH₂CH₂N (Me) C (O) CH₂CF_Three
H CH₂CH₂N (Me) C (O) CH₂SMe
H CH₂CH₂N (Me) C (O) CH₂S (O) Me
H CH₂CH₂N (Me) C (O) CH₂S (O)₂Me
H CH₂CH₂NHC (O) OMe
H CH₂CH₂NHC (O) OEt
H CH₂CH₂NHC (O) OPr-n
H CH₂CH₂NHC (O) OBu-t
H CH₂CH₂NHC (O) NHEt
H CH₂CH₂NHC (O) NHPr-n
H CH₂CH₂NHC (O) NHPr-i
H CH₂CH₂NHC (O) NHBu-t
H CH₂CH₂NHC (O) N (Me)₂
H CH₂CH₂NHSO₂Me
H CH₂CH₂NHSO₂Et
H CH₂CH₂NHSO₂CF_Three
H CH₂CH₂NHSO₂Ph
H CH₂CH₂NHSO₂N (Me)₂
H CH₂CH₂NHP (S) (OMe)₂
H CH₂CH₂NHP (S) (OEt)₂
H CH₂CH₂N (Me) SO₂Me
H CH₂CH₂N (Me) SO₂CF_Three
H CH₂CH₂N (Me) OMe
H CH₂CH (Me) NHC (O) Me
H CH₂CH (Me) NHC (O) CF_Three
H CH₂CH (Me) NHC (O) CH₂CF_Three
H CH₂CH (Me) NHC (O) CH₂SMe
H CH₂CH (Me) NHC (O) CH₂S (O) Me
H CH₂CH (Me) NHC (O) CH₂S (O)₂Me
H CH₂CH (Me) NHC (O) OMe
H CH (Me) CH₂NHC (O) Me
H CH (Me) CH₂NHC (O) CF_Three
H CH (Me) CH₂NHC (O) CH₂CF_Three
H CH (Me) CH₂NHC (O) CH₂SMe
H CH (Me) CH₂NHC (O) CH₂S (O) Me
H CH (Me) CH₂NHC (O) CH₂S (O)₂Me
H CH (Me) CH₂NHC (O) OMe
H CH₂CH₂CH₂NHC (O) Me
H CH₂CH₂CH₂NHC (O) OMe
H OMe
H OPr-i
H OCH₂CF_Three
H OCH₂CH = CH₂
H OCH₂CH = CHCl
H N (Me)₂
H N (Et)₂
H N (n-Pr)₂
H NHCH₂CF_Three
H N (Me) CH₂CF_Three
H N (CH₂CF_Three) C (O) Me
H N (CH₂CF_Three) C (O) OMe
H N (CH₂CF_Three) C (O) OEt
H NHCHO
H NHC (O) Me
H NHC (O) Et
H NHC (O) Pr-n
H NHC (O) Pr-i
H NHC (O) Pr-c
H NHC (O) Bu-n
H NHC (O) Bu-i
H NHC (O) Bu-s
H NHC (O) Bu-t
H NHC (O) Hex-n
H NHC (O) Hex-c
H NHC (O) CH₂CF_Three
H NHC (O) CH₂SMe
H NHC (O) CH₂S (O) Me
H NHC (O) CH₂S (O)₂Me
H NHC (O) OMe
H NHC (O) OEt
H NHC (O) OBu-t
H NHC (O) SMe
H NHC (S) OMe
H NHC (S) SMe
H N (Me) CHO
H N (Me) C (O) Me
H N (Me) C (O) Et
H N (Me) C (O) Pr-n
H N (Me) C (O) Pr-i
H N (Me) C (O) Pr-c
H N (Me) C (O) Bu-n
H N (Me) C (O) Bu-i
H N (Me) C (O) Bu-s
H N (Me) C (O) Bu-t
H N (Me) C (O) Hex-n
H N (Me) C (O) Hex-c
H N (Me) C (O) CH₂CF_Three
H N (Me) C (O) CH₂SMe
H N (Me) C (O) CH₂S (O) Me
H N (Me) C (O) CH₂S (O)₂Me
H N (Me) C (O) OMe
H N (Me) C (O) OEt
H N (Me) C (O) OBu-t
H N (Et) CHO
H N (Et) C (O) Me
H N (Et) C (O) Et
H N (Et) C (O) Pr-n
H N (Et) C (O) Pr-i
H N (Et) C (O) Pr-c
H N (Et) C (O) Bu-n
H N (Et) C (O) Bu-i
H N (Et) C (O) Bu-s
H N (Et) C (O) Bu-t
H N (Et) C (O) Hex-n
H N (Et) C (O) Hex-c
H N (Et) C (O) CH₂CF_Three
H N (Et) C (O) CH₂SMe
H N (Et) C (O) CH₂S (O) Me
H N (Et) C (O) CH₂S (O)₂Me
H N (Et) C (O) OMe
H N (Et) C (O) OEt
H N (Et) C (O) OBu-t
H NHC (O) NHMe
H NHC (O) NHCH₂CF_Three
H NHC (S) NHMe
H NHC (S) NHCH₂CF_Three
H C (O) NHMe
H C (O) NHEt
H C (O) NHPr-n
H C (O) NHPr-i
H C (O) NHPr-c
H C (O) NHBu-n
H C (O) NHBu-i
H C (O) NHBu-s
H C (O) NHBu-t
H C (O) NHCH₂CH₂F
H C (O) NHCH₂CH₂Cl
H C (O) NHCH₂CH₂Br
H C (O) NHCH₂CF_Three
H C (O) NHCH₂CF₂Cl
H C (O) NHCH₂CF₂CF_Three
H C (O) NHCH₂CF₂CF₂H
H C (O) NHCH₂CH₂OMe
H C (O) NHCH₂CH₂SMe
H C (O) NHCH₂CH₂S (O) Me
H C (O) NHCH₂CH₂S (O)₂Me
H C (O) NHCH₂CN
H C (O) NHCH₂CH = CH₂
H C (O) NHCH₂CH≡CH
H C (O) N (Me)₂
H C (O) N (Me) Et
H C (O) N (Me) Pr-n
H C (O) N (Me) Pr-i
H C (O) N (Me) Pr-c
H C (O) N (Me) Bu-n
H C (O) N (Me) Bu-i
H C (O) N (Me) Bu-s
H C (O) N (Me) Bu-t
H C (O) N (Me) CH₂CH₂F
H C (O) N (Me) CH₂CH₂Cl
H C (O) N (Me) CH₂CH₂Br
H C (O) N (Me) CH₂CF_Three
H C (O) N (Me) CH₂CF₂Cl
H C (O) N (Me) CH₂CF₂CF_Three
H C (O) N (Me) CH₂CF₂CF₂H
H C (O) N (Me) CH₂CH₂OMe
H C (O) N (Me) CH₂CH₂SMe
H C (O) N (Me) CH₂CH₂S (O) Me
H C (O) N (Me) CH₂CH₂S (O)₂Me
H C (O) N (Me) CH₂CN
H C (O) N (Me) CH₂CH = CH₂
H C (O) N (Me) CH₂CH≡CH
H C (S) NHMe
H C (S) NHEt
H C (S) NHPr-n
H C (S) NHPr-i
H C (S) NHPr-c
H C (S) NHBu-n
H C (S) NHBu-i
H C (S) NHBu-s
H C (S) NHBu-t
H C (S) NHCH₂CH₂F
H C (S) NHCH₂CH₂Cl
H C (S) NHCH₂CH₂Br
H C (S) NHCH₂CF_Three
H C (S) NHCH₂CF₂Cl
H C (S) NHCH₂CF₂CF_Three
H C (S) NHCH₂CF₂CF₂H
H C (S) NHCH₂CH₂OMe
H C (S) NHCH₂CH₂SMe
H C (S) NHCH₂CH₂S (O) Me
H C (S) NHCH₂CH₂S (O)₂Me
H C (S) NHCH₂CN
H C (S) NHCH₂CH = CH₂
H C (S) NHCH₂CH≡CH
H C (S) N (Me)₂
H C (S) N (Me) Et
H C (S) N (Me) Pr-n
H C (S) N (Me) Pr-i
H C (S) N (Me) Pr-c
H C (S) N (Me) Bu-n
H C (S) N (Me) Bu-i
H C (S) N (Me) Bu-s
H C (S) N (Me) Bu-t
H C (S) N (Me) CH₂CH₂F
H C (S) N (Me) CH₂CH₂Cl
H C (S) N (Me) CH₂CH₂Br
H C (S) N (Me) CH₂CF_Three
H C (S) N (Me) CH₂CF₂Cl
H C (S) N (Me) CH₂CF₂CF_Three
H C (S) N (Me) CH₂CF₂CF₂H
H C (S) N (Me) CH₂CH₂OMe
H C (S) N (Me) CH₂CH₂SMe
H C (S) N (Me) CH₂CH₂S (O) Me
H C (S) N (Me) CH₂CH₂S (O)₂Me
H C (S) N (Me) CH₂CN
H C (S) N (Me) CH₂CH = CH₂
H C (S) N (Me) CH₂CH≡CH
H C (O) CH₂CF3
H C (O) CH₂SMe
H C (O) CH₂S (O) Me
H C (O) CH₂S (O)₂Me
H D1-1a
H D1-1b
H D1-2a
H D1-2b
H D1-5a
H D1-5b
H D1-5c
H D1-6a
H D1-6b
H D1-6c
H D1-7a
H D1-8a
H D1-8b
H D1-8c
H D1-9a
H D1-9b
H D1-9c
H D1-10a
H D1-10b
H D1-10c
H D1-11a
H D1-12a
H D1-12b
H D1-12c
H D1-13a
H D1-13b
H D1-14a
H D1-14b
H D1-15a
H D1-15b
H D1-16a
H D1-17a
H D1-18a
H D1-19a
H D1-21a
H D1-21b
H D1-22a
H D1-23a
H D1-23b
H D1-24a
H D1-25a
H D1-27a
H D1-30a
H D1-31a
H D1-32a
H D1-34a
H D1-36a
H D1-37a
H D1-41a
H D1-43a
H D1-45a
H D1-46a
H D1-49a
H D1-51a
H D1-53a
H D1-59a
H D1-61a
H D1-63a
H D1-68a
H D1-75a
H D1-76a
H D1-76b
H D1-77a
H D1-77b
H D1-78a
H D1-78b
H D1-79a
H D1-81a
H D1-82a
H D1-84a
H D1-85a
H D1-87a
H D1-90a
H D1-100a
H D1-100b
H D1-100c
H D1-100d
H D1-100e
H D1-101a
H D1-101b
H D1-101c
H D1-101d
H D1-102a
H D1-102b
H D1-102c
H D1-102d
H D1-102e
H D1-102f
H D1-103a
H D1-104a
H D1-107a
H CH₂(D1-1a)
H CH₂(D1-1b)
H CH₂(D1-2a)
H CH₂(D1-2b)
H CH₂(D1-4a)
H CH₂(D1-4b)
H CH₂(D1-5a)
H CH₂(D1-5b)
H CH₂(D1-5c)
H CH₂(D1-6a)
H CH₂(D1-6b)
H CH₂(D1-6c)
H CH₂(D1-7a)
H CH₂(D1-8a)
H CH₂(D1-8b)
H CH₂(D1-8c)
H CH₂(D1-9a)
H CH₂(D1-9b)
H CH₂(D1-9c)
H CH₂(D1-10a)
H CH₂(D1-10b)
H CH₂(D1-10c)
H CH₂(D1-12a)
H CH₂(D1-12b)
H CH₂(D1-12c)
H CH₂(D1-13a)
H CH₂(D1-13b)
H CH₂(D1-14a)
H CH₂(D1-14b)
H CH₂(D1-15a)
H CH₂(D1-15b)
H CH₂(D1-16a)
H CH₂(D1-17a)
H CH₂(D1-18a)
H CH₂(D1-19a)
H CH₂(D1-20a)
H CH₂(D1-21a)
H CH₂(D1-21b)
H CH₂(D1-23a)
H CH₂(D1-23b)
H CH₂(D1-25a)
H CH₂(D1-27a)
H CH₂(D1-30a)
H CH₂(D1-31a)
H CH₂(D1-32a)
Me CH₂(D1-32a)
Et CH₂(D1-32a)
n-Pr CH₂(D1-32a)
i-Pr CH₂(D1-32a)
CH₂OCH_Three          CH₂(D1-32a)
CH₂CH₂OEt CH₂(D1-32a)
CH₂SCH_Three          CH₂(D1-32a)
CH₂CN CH₂(D1-32a)
CH₂CO₂Me CH₂(D1-32a)
CH₂CO₂Et CH₂(D1-32a)
CH₂CH = CH₂        CH₂(D1-32a)
CH₂CH≡CH CH₂(D1-32a)
C (O) CH_Three          CH₂(D1-32a)
C (O) Et CH₂(D1-32a)
C (O) Pr-n CH₂(D1-32a)
C (O) Pr-c CH₂(D1-32a)
C (O) Bu-t CH₂(D1-32a)
C (O) CH₂OCH_Three      CH₂(D1-32a)
C (O) CH₂SCH_Three      CH₂(D1-32a)
C (O) OMe CH₂(D1-32a)
C (O) OEt CH₂(D1-32a)
C (O) CH₂CH₂       CH₂(D1-32a)
C (O) CH₂CH₂       CH₂(D1-32a)
C (O) OCH₂CH = CH₂   CH₂(D1-32a)
C (O) SCH_Three         CH₂(D1-32a)
C (S) OCH_Three         CH₂(D1-32a)
C (S) SCH_Three         CH₂(D1-32a)
SMe CH₂(D1-32a)
SPh CH₂(D1-32a)
SNEt₂            CH₂(D1-32a)
SO₂Me CH₂(D1-32a)
SO₂Et CH₂(D1-32a)
SO₂Ph CH₂(D1-32a)
SO₂NMe₂          CH₂(D1-32a)
NH₂              CH₂(D1-32a)
NHMe CH₂(D1-32a)
NHCHO CH₂(D1-32a)
NHC (O) CH_Three        CH₂(D1-32a)
NHC (O) CF_Three        CH₂(D1-32a)
NHC (O) OCH_Three       CH₂(D1-32a)
N = C (CH_Three)₂        CH₂(D1-32a)
N = CHPh CH₂(D1-32a)
H CH₂(D1-33a)
H CH₂(D1-34a)
H CH₂(D1-35a)
H CH₂(D1-35b)
H CH₂(D1-36a)
H CH₂(D1-37a)
Me CH₂(D1-37a)
Et CH₂(D1-37a)
n-Pr CH₂(D1-37a)
i-Pr CH₂(D1-37a)
CH₂OCH_Three          CH₂(D1-37a)
CH₂CH₂OEt CH₂(D1-37a)
CH₂SCH_Three          CH₂(D1-37a)
CH₂CN CH₂(D1-37a)
CH₂CO₂Me CH₂(D1-37a)
CH₂CO₂Et CH₂(D1-37a)
CH₂CH = CH₂        CH₂(D1-37a)
CH₂CH≡CH CH₂(D1-37a)
C (O) CH_Three          CH₂(D1-37a)
C (O) Et CH₂(D1-37a)
C (O) Pr-n CH₂(D1-37a)
C (O) Pr-c CH₂(D1-37a)
C (O) Bu-t CH₂(D1-37a)
C (O) CH₂OCH_Three      CH₂(D1-37a)
C (O) CH₂SCH_Three      CH₂(D1-37a)
C (O) OMe CH₂(D1-37a)
C (O) OEt CH₂(D1-37a)
C (O) CH₂CH₂       CH₂(D1-37a)
C (O) CH₂CH₂       CH₂(D1-37a)
C (O) OCH₂CH = CH₂   CH₂(D1-37a)
C (O) SCH_Three         CH₂(D1-37a)
C (S) OCH_Three         CH₂(D1-37a)
C (S) SCH_Three         CH₂(D1-37a)
SMe CH₂(D1-37a)
SPh CH₂(D1-37a)
SNEt₂            CH₂(D1-37a)
SO₂Me CH₂(D1-37a)
SO₂Et CH₂(D1-37a)
SO₂Ph CH₂(D1-37a)
SO₂NMe₂          CH₂(D1-37a)
NH₂              CH₂(D1-37a)
NHMe CH₂(D1-37a)
NHCHO CH₂(D1-37a)
NHC (O) CH_Three        CH₂(D1-37a)
NHC (O) CF_Three        CH₂(D1-37a)
NHC (O) OCH_Three       CH₂(D1-37a)
N = C (CH_Three)₂        CH₂(D1-37a)
N = CHPh CH₂(D1-37a)
H CH₂(D1-38a)
H CH₂(D1-39a)
H CH₂(D1-40a)
H CH₂(D1-41a)
H CH₂(D1-42a)
H CH₂(D1-43a)
H CH₂(D1-45a)
H CH₂(D1-46a)
H CH₂(D1-49a)
H CH₂(D1-51a)
H CH₂(D1-53a)
H CH₂(D1-59a)
H CH₂(D1-61a)
H CH₂(D1-63a)
H CH₂(D1-68a)
H CH₂(D1-75a)
H CH₂(D1-76a)
H CH₂(D1-76b)
H CH₂(D1-77a)
H CH₂(D1-77b)
H CH₂(D1-78a)
H CH₂(D1-78b)
H CH₂(D1-79a)
H CH₂(D1-81a)
H CH₂(D1-82a)
H CH₂(D1-84a)
H CH₂(D1-85a)
H CH₂(D1-87a)
H CH₂(D1-90a)
H CH₂(D1-100a)
H CH₂(D1-100b)
H CH₂(D1-100c)
H CH₂(D1-100d)
H CH₂(D1-100e)
H CH₂(D1-101a)
H CH₂(D1-101b)
H CH₂(D1-101c)
H CH₂(D1-101d)
H CH₂(D1-102a)
H CH₂(D1-102b)
H CH₂(D1-102c)
H CH₂(D1-102d)
H CH₂(D1-102e)
H CH₂(D1-102f)
H CH₂(D1-103a)
H CH₂(D1-104a)
H CH₂(D1-105a)
H CH (Me) (D1-1a)
H CH (Me) (D1-2a)
H CH (Me) (D1-5a)
H CH (Me) (D1-5c)
H CH (Me) (D1-6c)
H CH (Me) (D1-8c)
H CH (Me) (D1-9b)
H CH (Me) (D1-9c)
H CH (Me) (D1-10b)
H CH (Me) (D1-10c)
H CH (Me) (D1-12b)
H CH (Me) (D1-12c)
H CH (Me) (D1-13b)
H CH (Me) (D1-14a)
H CH (Me) (D1-14b)
H CH (Me) (D1-15a)
H CH (Me) (D1-15b)
H CH (Me) (D1-16a)
H CH (Me) (D1-17a)
H CH (Me) (D1-18a)
H CH (Me) (D1-23b)
H CH (Me) (D1-27a)
H CH (Me) (D1-31a)
H CH (Me) (D1-32a)
H CH (Me) (D1-35a)
H CH (Me) (D1-36a)
H CH (Me) (D1-37a)
H CH (Me) (D1-39a)
H CH (Me) (D1-41a)
H CH₂C (O) NH (D1-1a)
H CH₂C (O) NH (D1-2a)
H CH₂C (O) NH (D1-5a)
H CH₂C (O) NH (D1-5c)
H CH₂C (O) NH (D1-6c)
H CH₂C (O) NH (D1-8c)
H CH₂C (O) NH (D1-9b)
H CH₂C (O) NH (D1-9c)
H CH₂C (O) NH (D1-10b)
H CH₂C (O) NH (D1-10c)
H CH₂C (O) NH (D1-12b)
H CH₂C (O) NH (D1-12c)
H CH₂C (O) NH (D1-13b)
H CH₂C (O) NH (D1-14a)
H CH₂C (O) NH (D1-14b)
H CH₂C (O) NH (D1-15a)
H CH₂C (O) NH (D1-15b)
H CH₂C (O) NH (D1-16a)
H CH₂C (O) NH (D1-17a)
H CH₂C (O) NH (D1-18a)
H CH₂C (O) NH (D1-23b)
H CH₂C (O) NH (D1-27a)
H CH₂C (O) NH (D1-31a)
H CH₂C (O) NH (D1-32a)
H CH₂C (O) NH (D1-35a)
H CH₂C (O) NH (D1-36a)
H CH₂C (O) NH (D1-37a)
H CH₂C (O) NH (D1-39a)
H CH₂C (O) NH (D1-41a)
H CH₂C (O) NH (D1-45a)
H CH₂C (O) NH (D1-46a)
H CH₂C (O) NH (D1-49a)
H CH₂C (O) NH (D1-51a)
H CH₂C (O) NH (D1-53a)
H CH₂C (O) NH (D1-59a)
H CH₂C (O) NH (D1-61a)
H CH₂C (O) NH (D1-63a)
H CH₂C (O) NH (D1-68a)
H CH₂C (O) NH (D1-75a)
H CH₂C (O) NH (D1-76a)
H CH₂C (O) NH (D1-76b)
H CH₂C (O) NH (D1-77a)
H CH₂C (O) NH (D1-77b)
H CH₂C (O) NH (D1-78a)
H CH₂C (O) NH (D1-78b)
H CH₂C (O) NH (D1-79a)
H CH₂C (O) NH (D1-82a)
H CH₂C (O) NH (D1-84a)
H CH₂C (O) NH (D1-85a)
H CH₂C (O) NH (D1-87a)
H CH₂C (O) NH (D1-90a)
H CH₂C (O) NH (D1-100a)
H CH₂C (O) NH (D1-100b)
H CH₂C (O) NH (D1-100c)
H CH₂C (O) NH (D1-100d)
H CH₂C (O) NH (D1-100e)
H CH₂C (O) NH (D1-101a)
H CH₂C (O) NH (D1-101b)
H CH₂C (O) NH (D1-101c)
H CH₂C (O) NH (D1-101d)
H CH₂C (O) NH (D1-105a)
H CH₂C (O) NHCH₂(D1-1a)
H CH₂C (O) NHCH₂(D1-2a)
H CH₂C (O) NHCH₂(D1-5a)
H CH₂C (O) NHCH₂(D1-5c)
H CH₂C (O) NHCH₂(D1-6c)
H CH₂C (O) NHCH₂(D1-8c)
H CH₂C (O) NHCH₂(D1-9b)
H CH₂C (O) NHCH₂(D1-9c)
H CH₂C (O) NHCH₂(D1-10b)
H CH₂C (O) NHCH₂(D1-10c)
H CH₂C (O) NHCH₂(D1-12b)
H CH₂C (O) NHCH₂(D1-12c)
H CH₂C (O) NHCH₂(D1-13b)
H CH₂C (O) NHCH₂(D1-14a)
H CH₂C (O) NHCH₂(D1-14b)
H CH₂C (O) NHCH₂(D1-15a)
H CH₂C (O) NHCH₂(D1-15b)
H CH₂C (O) NHCH₂(D1-16a)
H CH₂C (O) NHCH₂(D1-17a)
H CH₂C (O) NHCH₂(D1-18a)
H CH₂C (O) NHCH₂(D1-23b)
H CH₂C (O) NHCH₂(D1-27a)
H CH₂C (O) NHCH₂(D1-31a)
H CH₂C (O) NHCH₂(D1-32a)
H CH₂C (O) NHCH₂(D1-35a)
H CH₂C (O) NHCH₂(D1-36a)
H CH₂C (O) NHCH₂(D1-37a)
H CH₂C (O) NHCH₂(D1-39a)
H CH₂C (O) NHCH₂(D1-41a)
H CH₂C (O) NHCH₂(D1-45a)
H CH₂C (O) NHCH₂(D1-46a)
H CH₂C (O) NHCH₂(D1-49a)
H CH₂C (O) NHCH₂(D1-51a)
H CH₂C (O) NHCH₂(D1-53a)
H CH₂C (O) NHCH₂(D1-59a)
H CH₂C (O) NHCH₂(D1-61a)
H CH₂C (O) NHCH₂(D1-63a)
H CH₂C (O) NHCH₂(D1-68a)
H CH₂C (O) NHCH₂(D1-75a)
H CH₂C (O) NHCH₂(D1-76a)
H CH₂C (O) NHCH₂(D1-76b)
H CH₂C (O) NHCH₂(D1-77a)
H CH₂C (O) NHCH₂(D1-77b)
H CH₂C (O) NHCH₂(D1-78a)
H CH₂C (O) NHCH₂(D1-78b)
H CH₂C (O) NHCH₂(D1-79a)
H CH₂C (O) NHCH₂(D1-82a)
H CH₂C (O) NHCH₂(D1-84a)
H CH₂C (O) NHCH₂(D1-85a)
H CH₂C (O) NHCH₂(D1-87a)
H CH₂C (O) NHCH₂(D1-90a)
H CH₂C (O) NHCH₂(D1-102a)
H CH₂C (O) NHCH₂(D1-102b)
H CH₂C (O) NHCH₂(D1-102c)
H CH₂C (O) NHCH₂(D1-102d)
H CH₂C (O) NHCH₂(D1-102e)
H CH₂C (O) NHCH₂(D1-102f)
H CH₂C (O) NHCH₂(D1-103a)
H CH₂C (O) NHCH₂(D1-105a)
H NH (D1-7a)
H NH (D1-10c)
H NH (D1-22a)
H NH (D1-24a)
H NH (D1-32a)
H NC (O) Me (D1-32a)
H NC (O) OMe (D1-32a)
H NC (O) Et (D1-32a)
H NC (O) OEt (D1-32a)
H NC (O) CH₂CF_Three(D1-32a)
H NSO₂Me (D1-32a)
H NSO₂CF_Three(D1-32a)
H NSO₂Ph (D1-32a)
H NH (D1-35a)
H NH (D1-36a)
H NH (D1-37a)
H NH (D1-39a)
H NH (D1-43a)
H NH (D1-45a)
H NH (D1-49a)
H NH (D1-51a)
H NH (D1-53a)
H NH (D1-59a)
H NH (D1-61a)
H NH (D1-63a)
H NH (D1-105a)
H NH {D1-32b (3-Cl)}
H NH {D1-32b (4-Cl)}
H NH {D1-32b (5-Cl)}
H NH {D1-32b (6-Cl)}
H NH {D1-32b (4-CF_Three)}
H NH {D1-105b (2-Cl)}
H NH {D1-105b (3-Cl)}
H NH {D1-105b (4-Cl)}
H NH {D1-105b (2-Me)}
H NH {D1-105b (3-Me)}
H NH {D1-105b (4-Me)}
H CH₂CH₂(D1-1a)
H CH₂CH₂(D1-1b)
H CH₂CH₂(D1-2a)
H CH₂CH₂(D1-2b)
H CH₂CH₂(D1-5c)
H CH₂CH₂(D1-6c)
H CH₂CH₂(D1-7a)
H CH₂CH₂(D1-8c)
H CH₂CH₂(D1-9b)
H CH₂CH₂(D1-10b)
H CH₂CH₂(D1-10c)
H CH₂CH₂(D1-11a)
H CH₂CH₂(D1-20a)
H CH₂CH₂(D1-22a)
H CH₂CH₂(D1-24a)
H CH₂CH₂(D1-26a)
H CH₂CH₂(D1-28a)
H CH₂CH₂(D1-29a)
H CH₂CH₂(D1-32a)
H CH₂CH₂(D1-36a)
H CH₂CH₂(D1-37a)
H CH₂CH₂OCH₂(D1-1a)
H CH₂CH₂OCH₂(D1-1b)
H CH₂CH₂OCH₂(D1-2a)
H CH₂CH₂OCH₂(D1-2b)
H CH₂CH₂OCH₂(D1-4a)
H CH₂CH₂OCH₂(D1-4b)
H CH₂CH₂OCH₂(D1-5a)
H CH₂CH₂OCH₂(D1-5b)
H CH₂CH₂OCH₂(D1-5c)
H CH₂CH₂OCH₂(D1-6a)
H CH₂CH₂OCH₂(D1-6b)
H CH₂CH₂OCH₂(D1-6c)
H CH₂CH₂OCH₂(D1-7a)
H CH₂CH₂OCH₂(D1-8a)
H CH₂CH₂OCH₂(D1-8b)
H CH₂CH₂OCH₂(D1-8c)
H CH₂CH₂OCH₂(D1-9a)
H CH₂CH₂OCH₂(D1-9b)
H CH₂CH₂OCH₂(D1-9c)
H CH₂CH₂OCH₂(D1-10a)
H CH₂CH₂OCH₂(D1-10b)
H CH₂CH₂OCH₂(D1-10c)
H CH₂CH₂OCH₂(D1-12a)
H CH₂CH₂OCH₂(D1-12b)
H CH₂CH₂OCH₂(D1-12c)
H CH₂CH₂OCH₂(D1-13a)
H CH₂CH₂OCH₂(D1-13b)
H CH₂CH₂OCH₂(D1-14a)
H CH₂CH₂OCH₂(D1-14b)
H CH₂CH₂OCH₂(D1-15a)
H CH₂CH₂OCH₂(D1-15b)
H CH₂CH₂OCH₂(D1-16a)
H CH₂CH₂OCH₂(D1-17a)
H CH₂CH₂OCH₂(D1-18a)
H CH₂CH₂OCH₂(D1-19a)
H CH₂CH₂OCH₂(D1-20a)
H CH₂CH₂OCH₂(D1-21a)
H CH₂CH₂OCH₂(D1-21b)
H CH₂CH₂OCH₂(D1-23a)
H CH₂CH₂OCH₂(D1-23b)
H CH₂CH₂OCH₂(D1-25a)
H CH₂CH₂OCH₂(D1-27a)
H CH₂CH₂OCH₂(D1-30a)
H CH₂CH₂OCH₂(D1-31a)
H CH₂CH₂OCH₂(D1-32a)
H CH₂CH₂OCH₂(D1-33a)
H CH₂CH₂OCH₂(D1-34a)
H CH₂CH₂OCH₂(D1-35a)
H CH₂CH₂OCH₂(D1-35b)
H CH₂CH₂OCH₂(D1-36a)
H CH₂CH₂OCH₂(D1-37a)
H CH₂CH₂OCH₂(D1-38a)
H CH₂CH₂OCH₂(D1-39a)
H CH₂CH₂OCH₂(D1-40a)
H CH₂CH₂OCH₂(D1-41a)
H CH₂CH₂OCH₂(D1-42a)
H CH₂CH₂OCH₂(D1-43a)
H CH₂CH₂OCH₂(D1-45a)
H CH₂CH₂OCH₂(D1-46a)
H CH₂CH₂OCH₂(D1-49a)
H CH₂CH₂OCH₂(D1-51a)
H CH₂CH₂OCH₂(D1-53a)
H CH₂CH₂OCH₂(D1-59a)
H CH₂CH₂OCH₂(D1-61a)
H CH₂CH₂OCH₂(D1-63a)
H CH₂CH₂OCH₂(D1-68a)
H CH₂CH₂OCH₂(D1-75a)
H CH₂CH₂OCH₂(D1-76a)
H CH₂CH₂OCH₂(D1-76b)
H CH₂CH₂OCH₂(D1-77a)
H CH₂CH₂OCH₂(D1-77b)
H CH₂CH₂OCH₂(D1-78a)
H CH₂CH₂OCH₂(D1-78b)
H CH₂CH₂OCH₂(D1-79a)
H CH₂CH₂OCH₂(D1-81a)
H CH₂CH₂OCH₂(D1-82a)
H CH₂CH₂OCH₂(D1-84a)
H CH₂CH₂OCH₂(D1-85a)
H CH₂CH₂OCH₂(D1-87a)
H CH₂CH₂OCH₂(D1-90a)
H CH₂CH₂OCH₂(D1-100a)
H CH₂CH₂OCH₂(D1-100b)
H CH₂CH₂OCH₂(D1-100c)
H CH₂CH₂OCH₂(D1-100d)
H CH₂CH₂OCH₂(D1-100e)
H CH₂CH₂OCH₂(D1-101a)
H CH₂CH₂OCH₂(D1-101b)
H CH₂CH₂OCH₂(D1-101c)
H CH₂CH₂OCH₂(D1-101d)
H CH₂CH₂OCH₂(D1-102a)
H CH₂CH₂OCH₂(D1-102b)
H CH₂CH₂OCH₂(D1-102c)
H CH₂CH₂OCH₂(D1-102d)
H CH₂CH₂OCH₂(D1-102e)
H CH₂CH₂OCH₂(D1-102f)
H CH₂CH₂OCH₂(D1-103a)
H CH₂CH₂OCH₂(D1-104a)
H CH₂CH₂OCH₂(D1-105a)
H CH₂CH₂SCH₂(D1-1a)
H CH₂CH₂SCH₂(D1-1b)
H CH₂CH₂SCH₂(D1-2a)
H CH₂CH₂SCH₂(D1-2b)
H CH₂CH₂SCH₂(D1-4a)
H CH₂CH₂SCH₂(D1-4b)
H CH₂CH₂SCH₂(D1-5a)
H CH₂CH₂SCH₂(D1-5b)
H CH₂CH₂SCH₂(D1-5c)
H CH₂CH₂SCH₂(D1-6a)
H CH₂CH₂SCH₂(D1-6b)
H CH₂CH₂SCH₂(D1-6c)
H CH₂CH₂SCH₂(D1-7a)
H CH₂CH₂SCH₂(D1-8a)
H CH₂CH₂SCH₂(D1-8b)
H CH₂CH₂SCH₂(D1-8c)
H CH₂CH₂SCH₂(D1-9a)
H CH₂CH₂SCH₂(D1-9b)
H CH₂CH₂SCH₂(D1-9c)
H CH₂CH₂SCH₂(D1-10a)
H CH₂CH₂SCH₂(D1-10b)
H CH₂CH₂SCH₂(D1-10c)
H CH₂CH₂SCH₂(D1-12a)
H CH₂CH₂SCH₂(D1-12b)
H CH₂CH₂SCH₂(D1-12c)
H CH₂CH₂SCH₂(D1-13a)
H CH₂CH₂SCH₂(D1-13b)
H CH₂CH₂OCH₂(D1-14a)
H CH₂CH₂SCH₂(D1-14b)
H CH₂CH₂SCH₂(D1-15a)
H CH₂CH₂SCH₂(D1-15b)
H CH₂CH₂SCH₂(D1-16a)
H CH₂CH₂SCH₂(D1-17a)
H CH₂CH₂SCH₂(D1-18a)
H CH₂CH₂SCH₂(D1-19a)
H CH₂CH₂SCH₂(D1-20a)
H CH₂CH₂SCH₂(D1-21a)
H CH₂CH₂SCH₂(D1-21b)
H CH₂CH₂SCH₂(D1-23a)
H CH₂CH₂SCH₂(D1-23b)
H CH₂CH₂SCH₂(D1-25a)
H CH₂CH₂SCH₂(D1-27a)
H CH₂CH₂SCH₂(D1-30a)
H CH₂CH₂SCH₂(D1-31a)
H CH₂CH₂SCH₂(D1-32a)
H CH₂CH₂SCH₂(D1-33a)
H CH₂CH₂SCH₂(D1-34a)
H CH₂CH₂SCH₂(D1-35a)
H CH₂CH₂SCH₂(D1-35b)
H CH₂CH₂SCH₂(D1-36a)
H CH₂CH₂SCH₂(D1-37a)
H CH₂CH₂SCH₂(D1-38a)
H CH₂CH₂SCH₂(D1-39a)
H CH₂CH₂SCH₂(D1-40a)
H CH₂CH₂SCH₂(D1-41a)
H CH₂CH₂SCH₂(D1-42a)
H CH₂CH₂SCH₂(D1-43a)
H CH₂CH₂SCH₂(D1-45a)
H CH₂CH₂SCH₂(D1-46a)
H CH₂CH₂SCH₂(D1-49a)
H CH₂CH₂SCH₂(D1-51a)
H CH₂CH₂SCH₂(D1-53a)
H CH₂CH₂SCH₂(D1-59a)
H CH₂CH₂SCH₂(D1-61a)
H CH₂CH₂SCH₂(D1-63a)
H CH₂CH₂SCH₂(D1-68a)
H CH₂CH₂SCH₂(D1-75a)
H CH₂CH₂SCH₂(D1-76a)
H CH₂CH₂SCH₂(D1-76b)
H CH₂CH₂SCH₂(D1-77a)
H CH₂CH₂SCH₂(D1-77b)
H CH₂CH₂SCH₂(D1-78a)
H CH₂CH₂SCH₂(D1-78b)
H CH₂CH₂SCH₂(D1-79a)
H CH₂CH₂SCH₂(D1-81a)
H CH₂CH₂SCH₂(D1-82a)
H CH₂CH₂SCH₂(D1-84a)
H CH₂CH₂SCH₂(D1-85a)
H CH₂CH₂SCH₂(D1-87a)
H CH₂CH₂SCH₂(D1-90a)
H CH₂CH₂SCH₂(D1-100a)
H CH₂CH₂SCH₂(D1-100b)
H CH₂CH₂SCH₂(D1-100c)
H CH₂CH₂SCH₂(D1-100d)
H CH₂CH₂SCH₂(D1-100e)
H CH₂CH₂SCH₂(D1-101a)
H CH₂CH₂SCH₂(D1-101b)
H CH₂CH₂SCH₂(D1-101c)
H CH₂CH₂SCH₂(D1-101d)
H CH₂CH₂SCH₂(D1-102a)
H CH₂CH₂SCH₂(D1-102b)
H CH₂CH₂SCH₂(D1-102c)
H CH₂CH₂SCH₂(D1-102d)
H CH₂CH₂SCH₂(D1-102e)
H CH₂CH₂SCH₂(D1-102f)
H CH₂CH₂SCH₂(D1-103a)
H CH₂CH₂SCH₂(D1-104a)
H CH₂CH₂SCH₂(D1-105a)
H CH₂{D1-1c (3-Me)}
H CH₂{D1-1d (5-Cl)}
H CH₂{D1-2c (5-Br)}
H CH₂{D1-2d (5-Cl)}
H CH₂{D1-4c (5-Cl)}
H CH₂{D1-4d (5-Cl)}
H CH₂{D1-5d (3-Me)}
H CH₂{D1-5e (3-Me)}
H CH₂{D1-5f (5-Me)}
H CH₂{D1-6d (3-Cl)}
H CH₂{D1-6e (3-Me)}
H CH₂{D1-6f (5-Me)}
H CH₂{D1-7a (3-Me)}
H CH₂{D1-8d (3-Cl)}
H CH₂{D1-8e (3-CF_Three)}
H CH₂{D1-8f (5-Me)}
H CH₂{D1-9d (2-Me)}
H CH₂{D1-9e (2-Me)}
H CH₂{D1-9f (4-Me)}
H CH₂{D1-10e (2-Me)}
H CH₂{D1-10f (2-Cl)}
H CH₂{D1-10e (2-Br)}
H CH₂{D1-12d (4-Me)}
H CH₂{D1-12e (5-Me)}
H CH₂{D1-12f (5-Cl)}
H CH₂{D1-13c (Me)}
H CH₂{D1-13d (Cl)}
H CH₂{D1-14c (Me)}
H CH₂{D1-14d (Me)}
H CH₂{D1-15c (Cl)}
H CH₂{D1-15d (Me)}
H CH₂{D1-16b (Ph)}
H CH₂{D1-17b (Ph)}
H CH₂{D1-18b (Me)}
H CH₂{D1-19b (Cl)}
H CH₂{D1-20b (Me)}
H CH₂{D1-21c (Me)}
H CH₂{D1-21d (Me)}
H CH₂{D1-23c (t-Bu)}
H CH₂{D1-23d (Ph)}
H CH₂{D1-25b (Me)}
H CH₂{D1-27a (Me)}
H CH₂{D1-32b (3-Cl)}
H CH₂{D1-32b (4-Cl)}
H CH₂{D1-32b (5-Cl)}
H CH₂{D1-32b (6-Cl)}
H CH₂{D1-32b (3-Me)}
H CH₂{D1-32b (4-Me)}
H CH₂{D1-32b (5-Me)}
H CH₂{D1-32b (6-Me)}
H CH₂{D1-32b (5-CF_Three)}
H CH₂{D1-33b (4-CF_Three)}
H CH₂{D1-34b (3-Cl)}
H CH₂{D1-35c (3-Cl)}
H CH₂{D1-35d (3-Cl)}
H CH₂{D1-36b (2-Me)}
H CH₂{D1-37b (4-Me)}
H CH₂{D1-38b (2-Me)}
H CH₂{D1-39b (5-Me)}
H CH₂{D1-105b (2-Cl)}
H CH₂{D1-105b (3-Cl)}
H CH₂{D1-105b (4-Cl)}
H CH₂{D1-105b (2-Me)}
H CH₂{D1-105b (3-Me)}
H CH₂{D1-105b (4-Me)}
H CH₂{D1-105b (2-CF_Three)}
H CH₂{D1-105b (3-CF_Three)}
H CH₂{D1-105b (4-CF_Three)}
H CH₂{D1-105b (2-OMe)}
H CH₂{D1-105b (3-OMe)}
H CH₂{D1-105b (4-OMe)}
H CH₂CH₂{D1-7b (4-Cl)}
H CH₂CH₂{D1-10e (2-Cl)}
H CH₂CH₂{D1-11b (2-Me)}
H CH₂CH₂{D1-20b (4-Me)}
H CH₂CH₂{D1-22b (3-SMe)}
H CH₂CH₂{D1-24b (3-Me)}
H CH₂CH₂{D1-26b (4-CO₂Me)}
H CH₂CH₂{D1-28b (Me)}
H CH₂CH₂{D1-29a (Ph)}
H CH₂CH₂{D1-32b (3-Cl)}
H CH₂CH₂{D1-36b (2-Me)}
H CH₂CH₂{D1-37b (4-Me)
――――――――――――――――――――――――
  The compounds of the present invention are stored in warehouses, so-called agricultural pests that harm agricultural and horticultural crops and trees, so-called livestock pests that parasitize livestock and poultry, so-called sanitary pests that cause various adverse effects in the human living environment such as houses. It is possible to effectively control insects such as so-called stored grain pests that harm cereals and the like, and pests such as mites, crustaceans, molluscs, and nematodes that occur and harm in similar situations at low concentrations.

Specific examples of insects, mites, crustaceans, molluscs and nematodes that can be controlled using the compounds of the present invention include:
Chestnut gall wasp (Dryocosmus kuriphilus), Argentine ant Argentine ant (Linepithema humile), Gantai ant Army ant (Eciton burchelli, E. schmitti), Japanese carpenter ant (Camponotus japonicus), Yhihara ant Mona Pharaohant Bulldog ant (Myrmecia spp.), Fire Ant (Solenopsis spp.), Asian giant hornet (Vespa mandarina), Japanese yellow hornet (Vespa simillima), Large-ranged bee Large rose sawfly (Arge pagana) Hymenoptera insects such as pine sawfly (Neodiprion sertifer), chestnut wasp Chestnut sawfly (Apethymus kuri), sedge bee wasp Cabbage sawfly (Athalia infumata), bee turnip sawfly (Athalia rosae),
Pear leaf miner (Bucculatrix pyrivorella), tea leaf roller (Caloptilia theivora), golden leaf soy Apple leafminer (Phyllonorycter ringoniella), citrus leafminer (Phyllocnistis citrella), immobilized leaflet Persimmon fruit moth (Stathmopoda masinissa), Peach fruit moth (Carposina sasakii), Allium leafminer (Acrolepiopsis sapporensis), Yami leafminer (Acrolepiopsis suzukiella), Peach fruit moth (Pel fruit) ), Diamondback moth (Plutella xylostella), red stem borer (Chilo suppressalis), Shibatatsuga Bluegrass webworm (Parapediasia teterrella) Cabbage webworm (Hellula undalis), Rice leaf roller (Cnaphalocrocis medinalis), Yellow moth moth (Conogethes punctiferalis), Cotton moth (Diaphania indica), Mulberry pyras (Mulberry pyras) Ostrinia furnacalis), European corn borer (Ostrinia nubilalis), Azuki bean borer (Ostrinia scapulalis), Sorghum moth Lesser corn stalk borer (Elasmopalpus lignosellus), ella borer L Tree borer Peach tree borer (Synanthedon exitiosa), Cosca Shiba Cherry tree borer (Synanthedon hector), Kubiakasukashiba (Toleria romanovi), Iraga Oriental moth (Monema flavescens), Aura Iga (Parasa consocia), Hiloheira Oiraga (Parasa) lepida), Parasa siniea, Parana siniea, Artona martini, Illiberis pruni, Illiberis rotundata, Carpenter moth (Cossus insularis), Codlingmon lum, Cydia Fruit moth (Grapholita dimorpha), Oriental fruit moth (Grapholita molesta), Bean pod borer (Leguminivora glycinivorella), Bean podworm (Matsumuraeses phaseoli), Grapeberry moss (Grape berryite moth) Smaller tea tortrix (Adoxophyes honmai), Apple coconut oyster Summer fruit tortrix (Adoxophyes orana fasciata), Apple peach oyster Asiatic leafroller (Archips breviplicanus), Midareka kumamaki Apple tortrix (Archips fuscocupreanus) Oriental tea tortrix (Homona magnanima), Tobihamaki Dark fruit-tree tortrix (Pandemis heparana), Matsukareha Pine moth (Dendrolimus spectabilis), Tsukakareha Jananese hemlock caterpillar (Dendrolimus superans), Takekareha, Japanese bamboo thrix ha Euthrix potatoria, Oriental lappet (Gastropacha orientalis), Kunugia undans, Kunugia yamadai, Tomato hornworm (Manduca quinquemaculata), Tobacco hornworm (Alliga moth) cunea), Mulberry tiger moth (Lemyra imparilis), white flies (Eilema fuscodorsalis), black buckwheat (Eilema laevis), white moths udoconspersa), Swan moth (Sphrageidus similis), Gypsy moth (Lymantria dispar), White-spotted tussock moth (Orgyia thyellina), Rice green caterpillar (Naranga aenescens), Naranga aenescens leaf worm (Aedia leucomelas), mushroom Cabbage armyworm (Mamestra brassicae), Ayayoto Oriental armyworm (Pseudaletia separata), Japanese swordfish Lawn grass cutworm (Spodoptera depravata), Southern army worm Southern armyworm (ex armed worm) Fall army worm Fall armyworm (Spodoptera frugiperda), cotton leaf worm Cotton leafworm (Spodoptera littoralis), common cutworm (Spodoptera litura), giant bollworm (Helicoverpa armigera), tobacco moth Orienta l tobacco budworm (Helicoverpa assulta), tobacco bad worm Tobacco budworm (Heliothis virescens), American tobacco moth Corn earworm (Helicoverpa zea), Japanese red moth Black cutworm (Agrotis ipsilon), Kaburaya moth Turnip moth (Agrotis segetum) ), Honey beetle Threespotted plusia (Ctenoplusia agnata), soy bean looper, soybean looper (Pseudoplusia includens), nettle cabbage cabbage looper (Trichoplusia ni), mugwort Japanese giant looper (Ascotis selenaria), brass white white butterfly Lis , Lepidoptera (Lepidoptera) such as Cabbage white butterfly (Pieris rapae crucivora), Ichimongiseri Straight swift (Parnara guttata), cotton leaf worm cotton leafworm (Alabama argillacea), sugarcane borer (Diatraea sacharalis) Insect,
The fruit fly Melon fly (Bactrocera cucurbitae), the fruit fly Oriental fruit fly (Bactrocera dorsalis), the Queensland fruit fly Queensland fruit fly (Bactrocera tryoni), the fruit fly Japanese orange fly (Bactrocera tsuneonis), the Mediterranean fruit fly Mediterraneitis fly (Anastrepha ludens), ring-fly fly Apple maggot (Rhagoletis pomonella), rice leaf fly Rice leaf miner (Agromyza oryzae), leaf flyer Pea leaf miner (Chromatomyia horticola), oil leaf fly Cabbage leafminer (Liriomyza brassicae) ), Green leaf fly Stone leek leafminer (Liriomyza chinensis), green leaf fly Pea leafminer (Liriomyza huidobrensis), tomato leaf fly Tomato leafminer (Liriomyza sativae), bean leaf fly Serpentine leafminer (Liriom yza trifolii), Japanese fruit fly (Drosophila suzukii), Small leaf rice leaf miner (Hydrellia griseola), Tsetse fly (Glossina morsitans, G. palpalis), White fly, Forest fly (Hippobca) Melophagus ovinus), Onion fly (Delia antiqua), Seed corn maggot (Delia platura), sugar beet fly, Beet leaf miner (Pegomya cunicularia), Lesser house fly (Fannia canicularis), Sheep head fly (Hritae flyfly) ), Sweet fly (Morellia simplex), Face fly (Musca autumnalis), Housefly (Musca domestica), Australian bush fly (Musca vetustissima), Horn flies Horn fly (Haematobia irritans), Stable fly (Stable fly) Stomoxys calci trans, Calliphora lata, Bottle fly (Calliphora vicina), Old world screw-worm fly (Chrysomya bezziana), Blow fly (Chrysomya chloropyga), Oriental latrine fly (Chrysomya, Chrysomya America) New World screw-worm fly (Cochliomyia hominivorax), Black blow fly (Phormia regina), Northern blowfly (Protophormia terraenovae), sheep fly, Australian sheep blowfly (Lucilia cuprina), Green bottle fly (Lucilia illustris) Common green bottle fly (Lucilia sericata), Bot flies (Cuterebra spp.), Human fly botfly (Dermatobia hominis), Horse-nosed bot fly (Gasterophilus haemorrhoidalis), Horse-fly Horis bottest t fly (Gasterophilus nasalis), Bullflies Warble fly (Hypoderma bovis), Common cattle grub (Hypoderma lineatum), Sheep nasal bot fly (Oestrus ovis), Fresh fly Flesh fly (Sarcophaga carnaria), perch Srina ), Splayed deerfly (Chrysops caecutiens), Mekurabu Deer fly (Chrysops suavis), Common horse fly (Haematopota pluvialis), Greenhead horsefly (Greenhead horse fly (Tabanus nigrovittatus)) ), Soybean pod gall midge (Asphondylia yushimai), Hessian fly Hessian fly (Mayetiola destructor), mud wings Orange wheat blossom midge (Sitodiplosis mosellana), chick nuka Biting midge (Culicoides arakawae), L nipponens is), Black-tailed Blackfish (Prosimulium yezoensis), Black fly (Simulium ochraceum), African Malaria mosquito (Anopheles gambiae), Red-backed Shrimp (Anopheles hyrcanus sinesis), Anophelestosi aegypti), Asian tiger mosquito (Aedes albopictus), Chikaeka House mosquito (Culex pipiens molestus), Akaieka House mosquito (Culex pipiens pallens), Culex tritaeniorhynchus, moth P Diptera insects such as Telmatoscopus albipunctatus)
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),
Tobacco beetle (Lasioderma serricorne), Common bean weevil (Acanthoscelides obtectus), Adzuki bean beetle (Callosobruchus chinensis), Grape borer (Xylotrechus pyrrhoder beetle beetle) White-spotted longicorn beetle (Anoplophora malasiaca), Japanese pine sawyer (Monochamus alternatus), Yellow-spotted longicorn beetle (Psacothea hilaris), Colorado potato beetle Colorado beetle beetle (Phaedon cochleariae), rice leaf beetle Rice leaf beetle (Oulema oryzae), spotted leaf beetle (Demotina fasciculata), leaf beetle Cucurbit leaf beetle (Aulacophora femoralis) Beet flea beetle (Chaetocnema concinna), Northern corn rootworm (Diabrotica barberi), Southern corn rootworm (Diabrotica undecimpunctata), Western corn rootworm Western corn rootworm (Diabrotica virgifera), Triped P flea beetle striolata), Solanum flea beetle (Psylliodes angusticollis), green beetle Mexican been beetle (Epilachna varivestis), large twenty-eight-spotted ladybird (Epilachna vigintioctomawata bird), (Epilachna vigintioctopunctata), Epuraea domina, Pollen beetle (Meligethes aeneus), Peach curculio (Rhynchites heros), Sweetpotato weevil (Cylas formicarius), potato weevil West Indian sweet potato weevil (Euscepes postfasciatus), cotton weevil Boll weevil (Anthonomus grandis), white-flying beetle White-fringed beetle (Graphognatus leucoloma), horned weevil weevil Octopus weevil Alfalfa weevil (Hypera postica), Granary weevil (Sitophilus granarius), Chinese weevil Maize weevil (Sitophilus zeamais), Shibao weevil Hunting billbug (Sphenophorus venatus vestitus), Ezo weevil weevil (Lissohoptrus oryzophilus), yellow mealworm (Tenebrio molitor), red flour beetle (Tribolium castaneum), sweet potato wireworm (Melanotus fortnumi), citrus fruit Tsuruga Sugarcane wireworm (Melanotus tamsuyensis), Coreus crested citrus flower chafer (Gametis jucunda), Nagachakogane, Yellowish elongate chafer (Heptophylla picea), Douganebuibu Cupreous chafer (Anomala cuprea), Japanese beetle ), Coleoptera insects such as Rove beetle (Paederus fuscipes),
Asian citrus psyllid (Diaphorina citri), pear sucker Pear sucker (Psylla pyrisuga), Chatel spiny whitefly (Aleurocanthus camelliae), orange spiny whitefly (Aleurocanthus spiniferus), white leaffly (Aleurocanthus spiniferus) Whitefly Sweetpotato whitefly (Bemisia tabaci), Citrus whitefly (Dialeurodes citri), Greenhouse whitefly (Trialeurodes vaporariorum), Pea aphid (Acyrthosiphon pisum), Bean accura bee crab aphid (Aphis fabae), Soybean Aphid (Aphis glycines), Cotton Aphid (Aphis gossypii), Apple Aphid (Aphis pomi), Spiraea aphid (Aphis pomi) Aphis spiraecola), Foxglove aphid (Aulacorthum solani), Leaf curl plum aphid (Brachycaudus helichrysi), Japanese aphid Cabbage aphid (Brevicoryne brassiae), Walnut aphid Wola Russian wheat aphid (Diuraphis noxia), plantain beetle Rosy apple aphid (Dysaphis plantaginea), peach beetle Mealy plum aphid (Hyalopterus pruni), black pea aphid Turnip aphid (Lipaphis erysimi), tulip beetle aphid Margin door aphid (Monellia caryella), peach aphid Green peach aphid (Myzus persicae), Lettuce aphid (Nasonovia ribisnigri), Nephia Onion aphid (N eotoxoptera formosana), wheat cherry-oat aphid (Rhopalosiphum padi), rice aphid Rice root aphid (Rhopalosiphum rufiabdominalis), wheat leaf aphid (Sitobion akebiae), English grain aito avenae), Greenbug (Schizaphis graminum), Black citrus aphid (Toxoptera aurantii), Brown citrus aphid (Toxoptera citricida), Apple weevil Wooly apple aphid (Eriosoma lanigerum), Grape aphid Viteus vitifolii), hornet beetle Indian wax scale (Ceroplastes ceriferus), ruby weevil Red wax scale (Ceroplastes rubens), citrus scale insect (Coccus pseudomagnoliarum), red beetle California red scale (Aonidiella aurantii), pear Scale scale San jose scale (Comstockaspis perniciosa), scale scale tea scale (Teori scale), scale scale scale Peony scale (Pseudaonidia paeoniae), scale beetle scale Mulberry scale (Pseudaulacaspis pentagona), white scale scale Pula scale pi Citrus snow scale (Unaspis citri), Euonymus scale (Unaspis euonymi), Agarhead scale (Unaspis yanonensis), Giant margarodid scale (Drosicha corottenta scale) purchasi), worm beetle Cotton mealy bug (Phenacoccus solani), citrus mealybug (Citrus mealybug (Planococcus citri)), Japanese mealybug (Planococcus kuraunhiae), stag beetle Comstock me alybug (Pseudococcus comstocki), grape mealybug (Pseudococcus maritimus), brown brown planthopper (Laodelphax striatella), brown rice planthopper (Nilaparvata lugens), white-backedella planta (Gifer) Leafhopper (Epiacanthus stramineus), Indian cotton leafhopper (Amrasca devastans), Greens leafhopper (Bardsley leafhopper (Balclutha saltuella)), Aster leafhopper (Macrosteles fascifrons), Green leafy leafhopper (Macrosteles striifrons) leafhopper (Nephotettix cincticeps), Grape Leafhopper (Arboridia apicalis), Potato Leafhopper (Empoasca fabae), Emporasca nipponica, Chanomi Green leafhopper (Empoasca onukii), Bean's smaller green leafhopper (Empoasca sakaii), Sleek bug (Dolycoris baccarum), Sea turtle Cabbage bug (Eurydema rugosa), Spined whitespot ), White-spotted stink bug (Eysarcoris lewisi), white-spotted stink bug (Eysarcoris ventralis), blue-headed stink bug Sheild bug (Glaucias subpunctatus), brown marmorink stink bug (Halyomorpha haly) Nezara antennata), Southern green stink bug (Nezara viridula), Redbanded stink bug (Piezodorus guildinii), Redbanded shield bug (Piezodorus hybneri), Brown-winged crossota (Brown-winged cross bug) Japanese black rice bug (Scotinophora lurida), Bean bug (Riptortus clavatus), Spider helicopter Rice bug (Leptocorisa chinensis), Japanese stink bug Rice stink bug (Cletus punctiger), Southern bug shrimp bug (Paradasynus spinosus), Red-backed Helicopod Bug Rhopalid bug (Rhopalus maculatus), American Red-footed Beetle True chinch bug (Blissus leucopterus), Japanese Red-headed Bug, Oriental chinch bug (Cavelerius saccharivorus) Red cotton bug (Dysdercus cingulatus), Venezuelan sand turtle Blood-sucking bug (Rhodnius prolixus), Mexican sand turtle Kissing bug (Triatoma dimidiata), Brazilian sand turtle Kissing bug (Triatoma infestans), green stink bug sternumhil Aster ), Blown Stink bag brown stink bug (Euschistus servus), Southern green stink bag (Nezara viridula), Tarnished plant bug (Lygus lineolaris), Stink bag (Dichelops furcatus), Sugarcans pitle bag sugarcane spittlebug (Mahanarva fimbriolata), azalea lace bug (Stephanitis pyrioides), bed bug Bed bug (Cimex lectularius), bluefin turtle Pale greenplant bug (Apolygus spinolae), western tarnished plant bug (Lygus hesperus) Tarnished plant bug (Lygus lineolaris), Nagamushikasikameka Rice stink bug (Stenodema sibiricum), Akasujikasikameka Sorghum plant bug (Stenotus rubrovittatus), Rice fossil turtle Rice leaf bug (Trigonotylus caelestlium) Hemiptera insects such as and fleahopper (Halticus insularis), Cotton fleahopper (Pseudatomoscelis seriatus), Flower thrips (Frankliniella intonsa), Green lizard Yellow tea thrips (Scirtothrips dorsalis), Southern thrips Melon thrips (Thrips palmi), Black thrips Onion thrips (Thrips tabaci), Japanese gall-forming thrips (optonicthrips) ,
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.
Desert locust (Schistocerca gregaria), Australian platypus locust Australian plague locust (Chortoicetes terminifera), locust grasshopper Migratory locust (Locusta migratoria), red-eye locust Lesser paddy grasshopper (Oxya japonica), red-eye grass oxen (Teleogryllus emma), Kela Oriental mole cricket (Gryllotalpa orientalis), etc., Orthoptera insects,
German cockroach (Blattella germanica), American cockroach (Periplaneta americana), Black cockroach Smoky-brown cockroach (Periplaneta jafonica), Japanese cockroach (Periplaneta japonica), Daikokuus tomato (America) Termite Western dry-wood termite (Incisitermes minor), Common termite Formosan subterranean termite (Coptotermes formosanus), Japanese termite Japanese subterranean termite (Reticulitermes speratus), Thai termite Black-winged subterranean termite (Odontotermes formosanus) ,
Rootfeeding springtail (Onychiurus folsomi), Siberian white beetle (Onychiurus sibiricus), Garb spring spring (Bourletiella hortensis), etc.
Isopoda crustaceans such as Pill bug (Armadillidium vulgare), common rough woodlouse (Porcellio scaber),
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,
Sayaashi mite Storage mite (Glycyphagus destructor), house ticks mite (Glycyphagus domesticus), wheat mite Brown-legged grain mite (Aleuroglyphus ovatus), black mite Cheese mite (Tyrophagus putrescentiae), spiny mite Tyrophas , Hyugata mite Feather mite (Pterolichus obtusus), chick mite Feather mite (Megninia cubitalis), white house mite American house dust mite (Dermatophagoides farinae), yellow leopard mite bovis), Dog ear mite (Otodectes cynotis), Cattle cypress mite Psoroptic mite (Psoroptes communis), Rabbit ear mite Rabbit ear mite (Psoroptes cuniculi), Sheep cucumber Nhizendani Sheep scab mite (Psoroptes ovis), SENKOU mites Itch mite (Sarcoptes scabiei), cat foraminous mites Cat mange mite (Notoedres cati) mites suborder such as (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), Tulip rust mites Wheat curl mite (Aceria tulipae), Black rust mites Pear rust mite (Eriophyes chibaensis), Peach bud insi ), Pearleaf blister mite (Eriophyes pyri), tea rust mite Tea rust mite (Acaphylla theavagrans), tomato rust mite Tomato russet mite (Aculops lycopersici), citrus mite Pink citrus rust mite (Aculops pelekassi) e rust mite (Aculus schlechtendali), Citrus rust mite Citrus rust mite (Phyllocoptruta oleivora), mite broad mite (Polyphagotarsonemus latus), cyclamen mite Cyclamen mite (Phytonemus pallidus), chuone mus mite Mite spider mite Citrus red mite (Panonychus citri), Mite spider mite Spider mite (Panonychus mori), Apple spider mite European red mite (Panonychus ulmi), Kanzawa spider mite Kanzawa spider mite (Tetranychus kanzawai), Nami spider mite Two mite Two-spot mite erythrocephalus), wheat mite Winter grain mite (Penthaleus major), Etsurombicula wichmanni, Miyagata pine tsutsumugi Trombiculid mite (Helenicula miyagawai), red tsutsugamushi (Leptotrombidium akamushi), yellow tsutsugamushi Prostigmata mites, such as Leptotrombidium pallida, Tsutsutsugamushi mite (Leptotrombidium scutellare),
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), northern fowl mite (Ornithonyssus sylviarum), honey bee mite Honeybee mite (Varroa destructor), honeybee mite Varroa mite Varroa mite (Mesostigmata) mites,
Pancreas (Architaenioglossa) gastropod, such as Apple snail (Pomacea canaliculata)
Giant African snail (Achatina fulica), terrestrial slug (Limax marginatus), slug slug (Meghimatium bilineatum), Korean round snail (Acusta despecta sieboldiana), Miss maimai Land snio (Euhadra mai) Eyes (Stylommatophora) gastropods,
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.
Rice white nematode (Aphelenchoides besseyi), Pine wood nematode (Bursaphelenchus xylophilus) nematode (Aphelenchida) nematode,
Potato cyst nematode (Globodera rostochiensis), wheat cyst nematode Cereal cyst nematode (Heterodera avenae), soybean cyst nematode (Seterbean cyst nematode (Heterodera glycines)), arenaria root nematode (Peterut root-Menot nematode) -knot nematode (Meloidogyne hapla), Southern root-knot nematode (Meloidogyne incognita), Java root-knot nematode (Meloidogyne javanica), Southern root-kion nematode Coffee root-lesion nematode (Pratylus nechade) Root-lesion nematode (Pratylenchus loosi), Cobb's root-lesion nematode (Pratylenchus penetrans), Crested nematode Walnut root-lesion nematode (Pratylenchus vulnus), etc. lenchida) nematode,
Oxyurida nematodes such as human worm Pinworm (Enterobius vermicularis), horse worm Equine pinworm (Oxyuris equi), rabbit worm Rabbit pinworm (Passalurus ambiguus),
Pig roundworm (Ascaris suum), Horse roundworm Horse roundworm (Parascaris equorum), Dog roundworm Dog roundworm (Toxascaris leonina), Dog roundworm Dog intestinal roundworm (Toxocara canis), Cat roundworm Feline roundworm (Toxocara cati), Cattle roundworm Large cattle roundworm (Toxocara vitulorum), Anisakis spp., Pseudoterranova spp., chicken caecal caecal worm (Heterakis gallinarum), chicken roundworm (Ascaridia galli) and other roundworms (Ascaridida) Nematode,
Medinaworm Guinea worm (Dracunculus medinensis), Dolores jaw-and-mouth beetle (Gnathostoma doloresi), Ganthostoma hispidum, Japanese jaw-and-mouth beetle (Gnathostoma nipponicum), Reddish-coloured worm (Gnathostoma spinigerum) Dog stomach worm (Physaloptera canis), cat stomach worm (Physaloptera felidis, P. praeputialis), lala gastroworm Feline / canine stomach worm (Physaloptera rara), oriental eyeworm Eye worm (Thelazia callipaeda), Bovine eyeworm (Thelazia rhodesi), Large mouth stomach worm (Draschia megastoma), Equine stomach worm (Habronema microstoma), Stomach worm (Habronema muscae), Beautiful esophagus Gullet worm ( Gongylonema pulchrum), Thick stomach worm (Ascarops strongylina), Parafilaria (Parafilaria bovicola), Parafilaria multipapillosa, Stephanofilaria okinawaensis), Bancroft filaria (Wuchereria bancrofti), Malay filamentous worm (Brugia malayi), Neck threadworm (Onchocerca cervicalis), Gibson filamentous worm (Onchocerca gibsoni), Cattle filarial worm (Onchocercer gautum) ), Convolvulus (Onchocerca volvulus), finger filamentous worm Bovine filarial worm (Setaria digitata), equine filamentous peritoneal worm (Setaria equina), papillary larva (Setaria labiatopapillosa), marshall filariae (Setaria marshalli), dog Spirurida nematodes, such as the 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 worm Common tapeworm (Moniezia benedeni), expanded tapeworm Sheep tapeworm (Moniezia expansa), Stysia 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) 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 Trypanosoma cruzi, Trypanosoma equiperdum, Trypanosoma evansi, etc. Kinotoplastida flagellates,
However, pests in the field of agriculture and horticulture that can be controlled using the compounds of the present invention and external or internal parasites such as livestock, poultry, and pet animals are not limited to these.

  Furthermore, the compound of the present invention is also effective against pests that have developed resistance to existing insecticides such as organophosphorus compounds, carbamate compounds, and pyrethroid compounds.

  That is, the compound of the present invention is composed of the order of mucous eyes (Coleoptera), reticulates (Roaches), straight moths (Grasshoppers), termites, common moths (Thrips), hemimorphs (stink bugs and leafhoppers). Eyes), Lepidoptera (Lepidoptera), Coleoptera (Coleoptera), Hymenoptera (Hymenoptera), Diptera (Flyidae), Islamic (Flea), Liceid, and other insects, ticks In addition, pests belonging to gastropods and nematodes can be effectively controlled at low concentrations. On the other hand, the compounds of the present invention are extremely useful with little adverse effect on mammals, fish, crustaceans and beneficial insects (beneficial insects such as bees and bumblebees, natural enemies such as honeybees, wasps, mistletoe flies, mosquitoes, and mites). Has features.

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

  Examples of the solid carrier include quartz, calcite, gypsum, dolomite, chalk, kaolinite, pyrophyllite, sericite, halosite, metahalosite, kibushi clay, glazed clay, porcelain stone, siegrite, and allophane. , Shirasu, Kira, Talc, Bentonite, Activated clay, Acid clay, Pumice, Attapulgite, Zeolite and diatomite Baked products such as magnesium carbonate, calcium carbonate, sodium carbonate, sodium bicarbonate, ammonium sulfate, sodium sulfate, magnesium sulfate, diammonium hydrogen phosphate, ammonium dihydrogen phosphate and potassium chloride, such as glucose, fructose , And Sugars such as sugar and lactose, polysaccharides such as starch, powdered cellulose and dextrin, organic materials such as urea, urea derivatives, benzoic acid and benzoic acid salts, such as wood flour, cork flour, corn cobs, walnut shells and Examples include plants such as tobacco stalks, fly ash, white carbon (for example, hydrous synthetic silica, anhydrous synthetic silica, hydrous synthetic silicate, etc.) and fertilizers.

Examples of the liquid carrier include xylene, alkyl (C ₉ or C ₁₀ etc.) benzene, phenyl xylyl ethane and alkyl (C ₁ or C ₃ etc.) naphthalene and other aromatic hydrocarbons, machine oil, normal paraffin, isoparaffin and Aliphatic hydrocarbons such as naphthene, mixtures of aromatic and aliphatic hydrocarbons such as kerosene, alcohols such as ethanol, isopropanol, cyclohexanol, phenoxyethanol and benzyl alcohol, ethylene glycol, propylene glycol, diethylene glycol, hexylene glycol , Polyhydric alcohols such as polyethylene glycol and polypropylene glycol, propyl cellosolve, butyl cellosolve, phenyl cellosolve, propylene glycol monomethyl ether, propylene glycol Ethers such as ethyl monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether and propylene glycol monophenyl ether, ketones such as acetophenone, cyclohexanone and γ-butyrolactone, fatty acid methyl esters, dialkyl esters of succinic acid, dialkyl esters of glutamic acid, adipine esters such as dialkyl ester and dialkyl phthalate esters, N- alkyl (C _1, C ₈ or C _12, etc.) acid amide pyrrolidone, soybean oil, linseed oil, rapeseed oil, coconut oil, such as cottonseed oil and castor oil Examples include fats and oils, dimethyl sulfoxide and water.

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

  Examples of the surfactant include polyoxyethylene alkyl ether, polyoxyethylene alkyl (mono or di) phenyl ether, polyoxyethylene (mono, di or tri) styryl phenyl ether, polyoxyethylene polyoxypropylene block copolymer, polyoxyethylene Ethylene fatty acid (mono or di) ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, castor oil ethylene oxide adduct, acetylene glycol, acetylene alcohol, ethylene oxide adduct of acetylene glycol, ethylene oxide adduct of acetylene alcohol and alkyl Nonionic surfactants such as glycosides, alkyl sulfate esters, alkylbenzene sulfonates, lignin sulfonates, alkyls Rufosuccinate, naphthalene sulfonate, alkyl naphthalene sulfonate, salt of formalin condensate of naphthalene sulfonic acid, salt of formalin condensate of alkyl naphthalene sulfonic acid, polyoxyethylene alkyl ether sulfate or phosphate ester salt, polyoxyethylene (Mono or di) alkyl phenyl ether sulfate or phosphate ester salt, polyoxyethylene (mono, di or tri) styryl phenyl ether sulfate or phosphate ester salt, polycarboxylate (eg polyacrylate, polymaleate and maleate) Copolymer of acid and olefin, etc.) and anionic surfactants such as polystyrene sulfonate, cationic surfactants such as alkylamine salts and alkyl quaternary ammonium salts, and amphoteric interfaces such as amino acid type and betaine type Sexual agents, silicone-based surfactants and fluorinated surfactants.

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

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

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

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

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

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

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

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

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

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

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

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

  As hydrophobic phase (oil), paraffin oil, silicone oil, sesame oil, almond oil, castor oil, synthetic triglyceride, ethyl stearate, di-n-butyryl adipate, hexyl laurate, dipropylene glycol pelargonate, branched chain Of a short fatty acid having a chain length and a saturated fatty acid having a chain length of C16 to C18, isopropyl myristate, isopropyl palmitate, capryl / caprate of a saturated fatty alcohol having a chain length of C12 to C18, isopropyl stearate, oleyl oleate Decyl oleate, ethyl oleate, ethyl lactate, waxy fatty acid ester, dibutyl phthalate, diisopropyl adipate, isotridecyl alcohol, 2-octyldodecanol, cetyl stearyl alcohol, oleyl alcohol It is.

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

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

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

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

  Next, formulation examples of the preparation when the compound of the present invention is used are shown. However, the formulation examples of the present invention are not limited to these. In the following formulation examples, “parts” means parts by weight.

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

[Milk]
Compound of the present invention 0.1-30 parts Liquid carrier 45-95 parts Surfactant 4.9-15 parts Others 0-10 parts Others include, for example, spreading agents, decomposition inhibitors, and the like.

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

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

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

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

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

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

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

[Formulation Example 1] wettable powder Compound No.1-001 20 parts pyrophyllite 74 parts Solpol 5039 4 parts (mixture of nonionic surfactant and anionic surfactant: Toho Chemical Co., Ltd.) Product name)
Carplex # 80D 2 parts (Synthetic hydrous silicic acid: Shionogi & Co., Ltd. trade name)
The above is uniformly mixed and ground to obtain a wettable powder.

[Formulation Example 2] Milk Compound of the present invention No.1-001 5 parts Xylene 75 parts N-methylpyrrolidone 15 parts Solpol 2680 5 parts (mixture of nonionic surfactant and anionic surfactant: Toho Chemical Industry (Product name)
The above is uniformly mixed to obtain an emulsion.

[Formulation Example 3] Suspension Agent Compound No.1-001 25 parts Agrisol S-710 10 parts (Nonionic Surfactant: Kao Corporation trade name)
LUNOX 1000C 0.5 part (anionic surfactant: Toho Chemical Industries, Ltd. trade name)
Xanthan gum 0.2 parts water 64.3 parts After uniformly mixing the above, wet pulverize to make a suspension.

[Composition Example 4] Granule wettable powder Compound No.1-001 of the present invention 75 parts Hytenol NE-15 5 parts (anionic surfactant: trade name of Daiichi Kogyo Seiyaku Co., Ltd.)
Vanillex N 10 parts (anionic surfactant: Nippon Paper Industries Co., Ltd. trade name)
Carplex # 80D 10 parts (Synthetic hydrous silicic acid: Shionogi Pharmaceutical Co., Ltd. trade name)
After uniformly mixing and pulverizing the above, a small amount of water is added, stirred and mixed, granulated with an extrusion granulator, and dried to obtain a granulated wettable powder.

[Formulation Example 5] Granules Invention compound No. 1-101 5 parts Bentonite 50 parts Talc 45 parts After uniformly mixing and pulverizing the above, a small amount of water is added and stirred and granulated using an extrusion granulator. And dried into granules.

[Composition Example 6] Powder Compound of the present invention No.1-001 3 parts Carplex # 80D 0.5 part (Synthetic hydrous silicic acid: Shionogi Pharmaceutical Co., Ltd. trade name)
Kaolinite 95 parts Diisopropyl phosphate 1.5 parts The above is uniformly mixed and ground to obtain a powder.

  In use, the above preparation is diluted 1 to 10000 times with water or sprayed directly without dilution.

[Formulation Example 7] wettable powder preparation Compound No. 1-001 of the present invention 25 parts sodium diisobutylnaphthalenesulfonate 1 part calcium n-dodecylbenzenesulfonate 10 parts alkylaryl polyglycol ether 12 parts naphthalenesulfonic acid formalin condensate Sodium salt 3 parts Emulsion type silicone 1 part Silicon dioxide 3 parts Kaolin 45 parts [Formulation Example 8] Water-soluble thickener preparation Compound No.1-001 20 parts Polyoxyethylene lauryl ether 3 parts Sodium dioctyl sulfosuccinate 3. 5 parts dimethyl sulfoxide 37 parts 2-propanol 36.5 parts [Formulation Example 9] Solution for spraying the present compound No.1-001 2 parts dimethyl sulfoxide 10 parts 2-propanol 35 parts acetone 53 parts [Formulation Example 10] transdermal Solution for administration The present compound No.1-001 5 Parts hexylene glycol 50 parts isopropanol 45 parts [Formulation Example 11] Solution for transdermal administration Compound No. 1-001 5 parts propylene glycol monomethyl ether 50 parts Dipropylene glycol 45 parts [Formulation example 12] transdermal administration (instillation) ) Solution for the Invention Compound No.1-001 2 parts Light Liquid Paraffin 98 parts [Formulation Example 13] Solution for the transdermal administration (drip) Compound No.1-001 2 parts Light Liquid Paraffin 58 parts Olive Oil 30 parts ODO -H 9 parts Shin-Etsu Silicone 1 part In addition, when the compound of the present invention is used as an agrochemical, other types of herbicides, various insecticides, acaricides, nematicides, You may mix and apply with a disinfectant, a plant growth regulator, a synergist, a fertilizer, a soil conditioner, etc.

  In particular, when mixed with other pesticides or plant hormones, the cost can be reduced by reducing the amount of applied medicine, the insecticidal spectrum can be expanded by the synergistic action of the mixed drugs, and higher pest control effects can be expected. At this time, a combination with a plurality of known agricultural chemicals is also possible. Examples of the type of agricultural chemical used in combination with the compound of the present invention include compounds described in The Pesticide Manual 15th edition, 2009, and the like. Specific examples of common names are as follows, but the general names are not necessarily limited to these.

  Bactericides: acibenzolar-S-methyl, acylaminobenzamide, acypetacs, aldimorph, ametoctradin, amisulbrom, amobam, ampropyl Phos (ampropyfos), anilazine, azaconazole, azithiram, azoxystrobin, barium polysulfide, benalaxyl, benalaxyl-M, benodaril (Benodanil), benomyl, benquinox, bentaluron, benthiavalicarb, benthiazole, benzamacril, benzamorf, bethoxazine, Binapacryl Biphenyl, bitertanol, blasticidin-S, bixafen, bordeaux mixture, boscalid, bromoconazole, bupirimate, buthiobate (Buthiobate), calcium polysulfide, calcium polysulfide, captafol, captan, carpropamid, carbamorph, carbendazim, carboxin (Carboxin), carvone, cheshunt mixture, chinomethionat, clobenthiazone, chloraniformethane, chloranil, chlorfenazol, Chloroneb (c hloroneb), chloropicrin, chlorothalonil, chlorquinox, chlozolinate, climbazole, clotrimazole, copper acetate, basic copper carbonate (copper carbonate, basic), cupric hydroxide, copper naphthenate, copper oleate, copper oxychloride, copper sulfate, basic sulfuric acid Copper sulfate, basic, copper zinc chromate, cufraneb, cuprobam, cyazofamid, cyclafuramid, cycloheximide, cyflufenamid, Simoxanil, cypendazole, cyproconazole (cyp) roconazol), cyprodinil, cyprofuram, dazomet, debacarb, decaentin, dehydroacetic acid, dichlorfluanid, dichlone, Dichlorophen, dichlozoline, diclobutrazol, diclocymet, diclomedine, dicloran, etc.

  Bactericides (continued): diethofencarb, difenoconazole, diflumetorim, dimethirimol, dimethomorph, dimoxystrobin, diniconazole-M, diniconazole-M, diniconazole-M M), dinobuton, dinocap, dinocap-4, dinocap-6, dinoton, dinosulfon, dinoterbon, diphenylamine ), Dipyrithione, ditalimfos, dithianon, dodemorph, dodine, drazoxolon, edifenphos, epoxiconazole, etaconazole, etaconazole Xham (ethaboxam), etem, etirimol, ethoxyquin, etridianol, famoxadone, fenarimol, febuconazole, fenamidone, phenaminosulf ), Fenapanil, fendazosulam, fenfuram, fenhexamid, fenitropan, fenoxanil, fenpiclonil, fenpropidin, fenpyrazamine (fenpyrazamine), fenpropimorph, fentin, ferbam, ferimzone, fluazinam, fludioxonil, flumetover, flumorph, full Fluopicolide, fluopyram, fluoroimide, fluotrimazole, fluoxastrobin, fluquinconazole, flusilazole, flusulfamide, fluthianyl (fluoxanil) flutianil), flutolanil, flutriafol, fluxapyroxad, folpet, fosetyl-aluminium, fuberidazole, fluralaxyl, flametopyr ( furametpyr), furcarbanil, furconazole, fluconazole-cis, furmecyclox, furphanate, furyonate, glyodin, griseofulvin, guazachi (Guazatine), halacrinate, hexachlorobenzene, hexaconazole, hexylthiofos, hydroxyquinoline sulfate, hymexazol, imazalil, Imibenconazole, iminoctadine, ipconazole, iprobenfos, iprodione, iprovalicarb, isoprothiolane, isovaledione, etc.

  Fungicide (continued): kasugamycin, kresoxim-methyl, mancopper, mancozeb, mandipropamid, maneb, mebenil, mecarbinzid , Mepanipyrim, mepronil, metalaxyl, metalaxyl-M, metam, metazoxolon, metconazole, metasulfocarb, metoxasulfocarb, metoxafloxam ), Methyl isothiocyanate, metiram, metinominostrobin, metrafenone, metsulfovax, milneb, microbutanil, microzoline (myclozo) lin), nabam, natamycin, nickel bis (dimethyldithiocarbamate), nitrostyrene, nitrothal-isopropyl, nuarimol, OH (OCH), octhilinone, offurace, orysastrobin, oxadixyl, oxine copper, oxycarboxin, oxpoconazole fumarate , Pefurzoate, penconazole, penflufen, penencycuron, penthiopyrad, o-phenylphenol, phosdiphen, phthalide, picoxis Robin (picoxystrobin), piperalin (piperalin), polycarbamate (polycarbamate), polyoxins (polyoxins), polyoxorim (polyoxorim), potassium azide (potassium hydrogen carbonate) (potassium hydrogen carbonate), proquinazid (proquinazid) probenazole), prochloraz, procymidone, propamocarb hydrochloride, propiconazole, propineb, prothiocarb, prothioconazole, pyracarbolid, Pyraclostrobin, pyrazophos, pyridinitril, pyrifenox, pyrimethanil, pyriofenone, pyroculone (pyroq) uilon, pyroxychlor, pyroxyfur, quinomethionate, quinoxyfen, quintozene, quinacetol-sulfate, quinazamid, quinazaazole, quinconazole rabenzazole).

  Fungicide (continued): sodium azide, sodium hydrogen carbonate, sodium hypochlorite, sulfur, spiroxamine, salicylanilide, silthiofam (Silthiofam), simeconazole, tebuconazole, tecnazene, tecoram, tetraconazole, thiabendazole, thiadifluor, thicyofen, thifluzamide thifluzamide, thiochlorfenphim, thiophanate, thiophanate-methyl, thioquinox, thiram, thiadinyl, tioxymid, tolcrophos-me Tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, triamiphos, triarimol, triazoxide, triazbutil, tributyltin oxide ), Trichlamide, tricyclazole, tridemorph, trifloxystrobin, triflumizole, triforine, triticonazole, validamycin, validamycin Examples include valifenalate, vinclozolin, zarilamide, zinc sulfate, zineb, ziram, zoxamide and shiitake mycelium extract.

  Bactericides: benzalkonium chloride, bithionol, bronopol, cresol, formaldehyde, nitrapyrin, oxolinic acid, oxyterracycline , Streptomycin and tecloftalam.

  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).

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

  The proton nuclear magnetic resonance chemical shift value described in the synthesis example was measured at 300 MHz using Me4Si (tetramethylsilane) as a reference material.

  The medium pressure preparative liquid chromatography described in the synthesis example used an intermediate pressure preparative apparatus (Yamazen Co., Ltd.); YFLC-Wprep (flow rate 18 ml / min, silica gel 40 μm column).

[Synthesis example]
Synthesis example 1
Production of 3-methyl-N ′-{4- (methylthio) benzylidene} -1- (pyridin-3-yl) -1H-pyrazole-4-carboxylic acid hydrazide (present compound 1-032)
Process 1
Preparation of ethyl 3-methyl-1- (pyridin-3-yl) -1H-pyrazole-4-carboxylate 3.0 g of ethyl 3-methyl-1H-pyrazole-4-carboxylate in a N, N-dimethylformamide solution After 5.3 g of 3-iodopyridine, 990 mg of copper iodide (monovalent), and 17.0 g of cesium carbonate were sequentially added, and the inside of the reaction vessel was replaced with nitrogen gas, the mixture was stirred at 120 ° C. for 4 hours. After completion of the reaction, 100 ml of water was added and extracted with 150 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 residue was purified by column chromatography eluting with n-hexane-ethyl acetate {1: 1 (volume ratio, hereinafter the same)} to obtain 2.4 g of the objective product as white crystals.
¹ H NMR (measurement solvent CDCl ₃ ) δ 8.98 (d, J = 2.4 Hz, 1H), 8.58 (d, J = 3.9 Hz, 1H), 8.38 (s, 1H), 8. 00-8.10 (m, 1H), 7.42 (dd, J = 4.8, 8.1 Hz, 1H), 4.34 (q, J = 7.2 Hz, 2H), 2.57 (s , 3H), 1.38 (t, J = 7.2 Hz, 3H).

Process 2
Preparation of 3-methyl-1- (pyridin-3-yl) -1H-pyrazole-4-carboxylic acid 3.9 g of ethyl 3-methyl-1- (pyridin-3-yl) -1H-pyrazole-4-carboxylate Was dissolved in 20 ml of ethanol, 1.9 g of potassium hydroxide and 10 ml of water were sequentially added, and the mixture was stirred at 50 ° C. for 1 hour. After completion of the reaction, the solvent was distilled off under reduced pressure. The reaction mixture was neutralized with an aqueous hydrochloric acid solution and then extracted with ethyl acetate (50 ml × 2). The obtained organic layer was dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 2.1 g of the desired product as a white solid.
¹ H NMR (measurement solvent DMSO-d6) δ 9.03 (m, 1H), 8.71 (s, 1H), 8.46 (d, J = 2.1 Hz, 1H), 8.18 (d, J = 8.4 Hz, 1H), 7.50 (dd, J = 8.4 Hz, 4.8 Hz, 1H), 2.40 (s, 3H)
Melting point: 200-210 ° C
Process 3
Production of {4- (methylthio) benzylidene} hydrazone To a solution of 10 g of 4- (methylthio) benzaldehyde oxime in 20 ml of ethanol was added 8.97 g of hydrazine monohydrate, and the mixture was stirred under ethanol reflux conditions for 2 hours. Further, 8.97 g of hydrazine monohydrate was added, and stirring was continued for 4 hours under the reflux condition of ethanol. After completion of the reaction, 50 ml of water was added to the reaction mixture, and the solid precipitated in the reaction mixture was removed by vacuum filtration. The obtained solid was dried to obtain 8.7 g of the desired product as a white solid.
¹ H NMR (measurement solvent CDCl ₃ ) δ 7.70 (s, 1H), 7.48 (d, J = 8.4 Hz, 2H), 7.23 (d, J = 8.4 Hz, 2H), 5. 52 (brs, 2H), 2.48 (s, 3H)
Melting point: 67-70 ° C
Process 4
Preparation of 3-methyl-N ′-{4- (methylthio) benzylidene} -1- (pyridin-3-yl) -1H-pyrazole-4-carboxylic acid hydrazide 3-methyl-1- (pyridin-3-yl) In a solution of 1.0 g of 1H-pyrazole-4-carboxylic acid in 15 ml of dichloromethane, 443 mg of triethylamine, 971 mg of {4- (methylthio) benzylidene} hydrazone, 840 mg of 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride Were sequentially added and stirred at room temperature for 12 hours. After completion of the reaction, 10 ml of water was added to the reaction mixture and extracted with 20 ml of chloroform. The obtained organic layer was washed with water, dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained solid was washed with diisopropyl ether to obtain 315 mg of the desired product as a pale yellow solid.
Melting point: 167-169 ° C
Synthesis example 2
Production of N- {1- (methoxyimino) -2- (methylthio) ethyl} -3-methyl-1- (pyridin-3-yl) -1H-pyrazole-4-amide (present compound 1-051)
Process 1
Preparation of methyl 2- (methylthio) ethaneimidothioate To a solution of 2.6 g of 2- (methylthio) ethanethioamide in 100 ml of acetonitrile were sequentially added 4.45 g of potassium carbonate and 3.64 g of methyl iodide and stirred overnight at room temperature. did. After completion of the reaction, the solvent was distilled off under reduced pressure, and 100 ml of water was added, followed by extraction with 100 ml of ethyl acetate. The obtained organic layer was washed with water, dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified with a silica gel column flowing out with n-hexane: ethyl acetate (2: 1) to obtain 1.5 g of the objective product as a brown oil.
¹ H NMR (measurement solvent CDCl ₃ ) δ 9.49 (brs, 1H), 3.40 (s, 2H), 2.38 (s, 3H), 2.10 (s, 3H)
Process 2
Preparation of N′-methoxy-2- (methylthio) acetimidamide Methyl 2- (methylthio) ethaneimidethioate 750 mg in ethanol 20 ml solution was added with triethylamine 843 mg and O-methylhydroxylamine hydrochloride 557 mg in order, and ethanol reflux conditions The mixture was stirred for 9 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, 30 ml of water was added, and the mixture was extracted with 50 ml of ethyl acetate. The obtained organic layer was washed with water, dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by a silica gel column flowing out with n-hexane: ethyl acetate (2: 1) to obtain 46 mg of the objective product as a yellow oil.
¹ H NMR (measurement solvent CDCl ₃ ) δ 4.81 (brs, 2H), 3.79 (s, 3H), 3.14 (s, 2H), 2.07 (s, 3H)
Process 3
Preparation of N- {1- (methoxyimino) -2- (methylthio) ethyl} -3-methyl-1- (pyridin-3-yl) -1H-pyrazole-4-amide 3-Methyl-1- (pyridine- To a solution of 670 mg of 3-yl) -1H-pyrazole-4-carboxylic acid in 4.5 ml of dichloromethane, 1.0 ml of oxalyl chloride and then 10 mg of N, N-dimethylformamide were added in this order, and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, the solvent was distilled off under reduced pressure. The obtained residue was added to a solution of 1.77 g of N′-methoxy-2- (methylthio) acetimidamide and 633 mg of 60 wt% sodium hydride (dispersed in mineral oil) in 10 ml of N, N-dimethylformamide at room temperature. Stir for 16 hours. After completion of the reaction, the reaction solution was added to 30 ml of water and then extracted with 100 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 n-hexane-ethyl acetate (3: 7) to obtain 320 mg of the desired product as a white solid.
Melting point: 124-125 ° C
Synthesis example 3
Production of 3-chloro-N- {1- (methoxyimino) -2- (methylthio) ethyl} -1- (pyridin-3-yl) -1H-pyrazole-4-amide (present compound 1-057)
Process 1
Preparation of ethyl 3-chloro-1H-pyrazole-4-carboxylate To 9.71 g of ethyl 1-tert-butyl-3-chloro-1H-pyrazole-4-carboxylate was added 30 ml of concentrated hydrochloric acid under ice cooling. Stir at room temperature overnight. Further, 10 ml of concentrated hydrochloric acid was added to the reaction mixture, and stirring was continued for a whole day and night. After completion of the reaction, the reaction mixture was cooled to 0 ° C., neutralized with an aqueous sodium hydroxide solution, and extracted with 100 ml of ethyl acetate. The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained solid was washed with n-hexane to obtain 6.28 g of the desired product as a white solid.
¹ H NMR (measurement solvent CDCl ₃ ) δ 11.2 (brs, 1H), 8.10 (s, 1H), 4.33 (q, J = 7.2 Hz, 2H), 1.36 (t, J = 7.2Hz, 3H)
Process 2
Preparation of ethyl 3-chloro-1- (pyridin-3-yl) -1H-pyrazole-4-carboxylate 10.2 g of ethyl 3-chloro-1H-pyrazole-4-carboxylate in 150 ml of N, N-dimethylformamide To this, 15.6 g of 3-iodopyridine, 2.23 g of copper iodide (monovalent), and 33.0 g of cesium carbonate were sequentially added. The inside of the reaction vessel was replaced with nitrogen gas, followed by stirring at 130 ° C. for 5 hours. After completion of the reaction, the reaction mixture was allowed to cool to room temperature and 100 ml of 1N aqueous sodium hydroxide solution was added. Impurities in the reaction mixture were removed by Celite filtration under reduced pressure, and the obtained filtrate was extracted with 100 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 n-hexane-ethyl acetate (1: 1) to obtain 7.56 g of the desired product as a white solid.
Melting point: 90-93 ° C.

Process 3
Preparation of 3-chloro-1- (pyridin-3-yl) -1H-pyrazole-4-carboxylic acid 16.8 g of ethyl 3-chloro-1- (pyridin-3-yl) -1H-pyrazole-4-carboxylate Was dissolved in 130 ml of ethanol, 5.6 g of potassium hydroxide and 130 ml of water were sequentially added, and the mixture was stirred overnight at room temperature. After completion of the reaction, the solvent was distilled off under reduced pressure, and a 2N hydrochloric acid aqueous solution was added to the residue to adjust the pH to 4. The precipitated solid was removed by filtration under reduced pressure, and the extracted solid was washed with 400 ml of water. To the obtained solid, 200 ml of toluene was added, and water contained in the solid was removed by azeotropic dehydration under reflux. After completion of dehydration, the solid was removed by filtration to obtain 14.5 g of the desired product as light pink crystals.
Melting point: 275-282 ° C.

Process 4
Preparation of 3-chloro-N- {1- (methoxyimino) -2- (methylthio) ethyl} -1- (pyridin-3-yl) -1H-pyrazole-4-amide 3-chloro-1- (pyridine- To a solution of 1.0 g of 3-yl) -1H-pyrazole-4-carboxylic acid in 6 ml of dichloromethane was added 1.0 ml of oxalyl chloride and 10 mg of N, N-dimethylformamide in this order, and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, the solvent was distilled off under reduced pressure. After distilling off the solvent, the residue obtained was dissolved in 2.4 g of N′-methoxy-2- (methylthio) acetimidamide and 860 mg of 60% by weight sodium hydride (dispersed in mineral oil) in 15 ml of N, N-dimethylformamide. And stirred at room temperature for 16 hours. After completion of the reaction, the reaction solution was poured into 30 ml of water and then extracted with 100 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 n-hexane-ethyl acetate (3: 7) to obtain 94 mg of the desired product as a white solid.
Melting point: 117-119 ° C
Synthesis example 4
Production of N- {1- (methoxyimino) -2-methyl-3- (methylthio) propyl} -3-methyl-1- (pyridin-3-yl) -1H-pyrazole-4-carboxamide (present compound 1 -082)
Process 1
Production of 2-methyl-3- (methylthio) propanenitrile To a solution of 15.0 g of methacrylonitrile in 50 ml of tetrahydrofuran was added 30% by weight aqueous potassium hydroxide solution and 16.4 g of S, S′-dimethyldithiocarbonate, and 90 ° C. For 5 hours. After completion of the reaction, 100 ml of water was added and extracted with 150 ml of diethyl ether. 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 silica gel column chromatography eluting with n-hexane-ethyl acetate 1: 1 to obtain 19.0 g of the desired product as a yellow oil.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 2.90-2.60 (m, 3H), 2.20 (s, 3H), 1.41 (d, J = 6.9 Hz, 3H)
Process 2
Preparation of N′-methoxy-2-methyl-3- (methylthio) propaneimidamide 2-methyl-3- (methylthio) propanenitrile 7.8 g of methanol in 11 ml solution of about 4M hydrogen chloride in 1,4-dioxane Was added and stirred at room temperature for 4 days. After completion of the reaction, the solvent of the reaction solution was distilled off under reduced pressure. To the obtained residue, 100 ml of methanol, 8.4 g of methoxyamine hydrochloride and 20.5 g of triethylamine were sequentially added and stirred at room temperature for 20 hours. After completion of the reaction, the solvent of the reaction solution was distilled off under reduced pressure. 100 ml of water was added to the resulting residue, and the mixture was extracted with 100 ml of ethyl acetate. 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 to obtain 6.4 g of the desired product as a pale yellow oil.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 4.56 (brs, 2H), 3.77 (s, 3H), 2.85-2.70 (m, 1H), 2.65-2. 45 (m, 2H), 2.14 (s, 3H), 1.26 (d, J = 6.9 Hz, 3H)
Process 3
Preparation of N- {1- (methoxyimino) -2-methyl-3- (methylthio) propyl} -3-methyl-1- (pyridin-3-yl) -1H-pyrazole-4-carboxamide Ethyl 3-methyl- 1- (Pyridin-3-yl) -1H-pyrazole-4-carboxylate 1.0 g was dissolved in 10 ml of N, N-dimethylformamide, and N′-methoxy-2-methyl-3- (methylthio) propaneimidamide was dissolved. 0.77 g and tertiary butoxy potassium 0.67 g were sequentially added. After completion of the addition, the mixture was stirred at room temperature for 30 minutes. After completion of the reaction, 50 ml of water was added and extracted with 50 ml of ethyl acetate. 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 medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (10: 1 to 1: 1) to obtain 0.5 g of the objective product as a pale yellow solid.
Melting point 66-71 ° C
Synthesis example 5
Preparation of 1- (5-fluoropyridin-3-yl) -N- {1- (methoxyimino) -2- (methylthio) ethyl} -3-methyl-1H-pyrazole-4-carboxamide (present compound 2- 001)
Process 1
Preparation of ethyl 1- (1-ethoxyethyl) -3-methyl-1H-pyrazole-4-carboxylate and ethyl 1- (1-ethoxyethyl) -5-methyl-1H-pyrazole-4-carboxylate To a solution of 7 g of methyl-1H-pyrazolecarboxylate in 100 ml of tetrahydrofuran was added 16 g of ethyl vinyl ether and 0.1 ml of concentrated hydrochloric acid. After completion of the addition, the mixture was stirred for 5 hours while refluxing tetrahydrofuran. After completion of the reaction, 150 ml of water was added to the reaction solution and extracted with 100 ml of ethyl acetate. 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 to obtain 8.5 g of the desired product as a yellow oil (isomer ratio 10: 3). ).
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ
(Isomer ratio 10) 8.00 (s, 1H), 5.41 (q, J = 5.7 Hz, 1H), 3.82 (s, 3H), 3.55-3.20 (m, 2H) ), 2.47 (s, 3H), 1.64 (d, J = 5.7 Hz, 3H), 1.16 (t, J = 7.2 Hz, 3H)
(Isomer ratio 3) 7.85 (s, 1H), 5.60 (q, J = 6.0 Hz, 1H), 3.82 (s, 3H), 3.55-3.20 (m, 2H) ), 2.66 (s, 3H), 1.70 (d, J = 6.0 Hz, 3H), 1.16 (t, J = 7.2 Hz, 3H)
Process 2
1- (1-Ethoxyethyl) -N- {1- (methoxyimino) -2- (methylthio) ethyl} -3-methyl-1H-pyrazole-4-carboxamide and 1- (1-ethoxyethyl) -N- Production of {1- (methoxyimino) -2- (methylthio) ethyl} -5-methyl-1H-pyrazole-4-carboxamide Ethyl 1- (1-ethoxyethyl) -3-methyl-1H- produced in Step 1 Mixture of pyrazole-4-carboxylate and ethyl 1- (1-ethoxyethyl) -5-methyl-1H-pyrazole-4-carboxylate 1.5 g of N, N-dimethylformamide in 13 ml of N′-methoxy-2 -(Methylthio) acetimidamide 1.02g and tertiary butoxy potassium 1.2g were added sequentially. After completion of the addition, the mixture was stirred at room temperature for 3 hours. After completion of the reaction, 20 ml of water was added to the reaction solution and extracted with ethyl acetate (15 ml × 2). 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 eluting with n-hexane-ethyl acetate (9: 1 to 1: 1) to obtain 1.5 g of the desired product as a yellow oil (isomer). Body ratio 5: 1).
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ
(Isomer ratio 5) 8.44 (brs, 1H), 8.00 (s, 1H), 5.43 (q, J = 6.0 Hz, 1H), 3.92 (s, 2H), 3. 79 (s, 3H), 3.60-3.30 (m, 2H), 2.52 (s, 3H), 2.14 (s, 3H), 1.65 (d, J = 6.0 Hz, 3H), 1.18 (t, J = 6.9 Hz, 3H)
(Isomer ratio 1) 8.44 (brs, 1H), 7.74 (s, 1H), 5.62 (q, J = 6.0 Hz, 1H), 3.91 (s, 2H), 3. 80 (s, 3H), 3.60-3.30 (m, 2H), 2.68 (s, 3H), 2.07 (s, 3H), 1.70 (d, J = 6.0 Hz, 3H), 1.17 (t, J = 6.9 Hz, 3H)
Process 3
Production of N- {1- (methoxyimino) -2- (methylthio) ethyl} -3-methyl-1H-pyrazole-4-carboxamide 1- (1-ethoxyethyl) -N- {1 produced in Step 2 -(Methoxyimino) -2- (methylthio) ethyl} -3-methyl-1H-pyrazole-4-carboxamide and 1- (1-ethoxyethyl) -N- {1- (methoxyimino) -2- (methylthio) To a solution of ethyl} -5-methyl-1H-pyrazole-4-carboxamide 1.16 g in 12 ml of tetrahydrofuran was added 4.4 ml of 1N aqueous hydrochloric acid. After completion of the addition, the mixture was stirred at room temperature for 4 hours. After completion of the reaction, the reaction solution was neutralized with a saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate (15 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 eluting with n-hexane-ethyl acetate (9: 1 to 1: 2) to obtain 0.47 g of the desired product as a white solid.
Melting point: 41-43 ° C
Process 4
Preparation of 1- (5-fluoropyridin-3-yl) -N- {1- (methoxyimino) -2- (methylthio) ethyl} -3-methyl-1H-pyrazole-4-carboxamide N- {1- ( To a solution of 470 mg of N, N-dimethylformamide in 470 mg of methoxyimino) -2- (methylthio) ethyl} -3-methyl-1H-pyrazole-4-carboxamide, 225 mg of 3,5-difluoropyridine and 950 mg of cesium carbonate were sequentially added. . After completion of the addition, the mixture was stirred at 80 ° C. for 4 hours. After completion of the reaction, 15 ml of water was added to the reaction solution, and extracted with ethyl acetate (15 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 resulting residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (9: 1 to 1: 2), followed by n-hexane-ethyl acetate (2: 3). Recrystallization from the mixed solution gave the desired product (135 mg) as a white solid.
Melting point: 121-122 ° C
Reference Example The following compound was synthesized using the same method as in Step 2 of Synthesis Example 4.

N′-methoxy-3- (methylthio) propaneimidamide (isomer ratio 5: 1)
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ
(Isomer ratio 5) 4.69 (brs, 2H), 3.77 (s, 3H), 2.73 (t, J = 7.2H, 2H), 2.42 (t, J = 7.2 Hz) , 2H), 2.15 (s, 3H)
(Isomer ratio 1) 5.82 (brs, 2H), 3.70 (s, 3H), 3.52 (s, 3H), 3.20 (t, J = 6.3H, 2H), 2. 58 (t, J = 6.3 Hz, 2H)
This invention compound can be manufactured according to the said manufacturing method and an Example. Although the example of this invention compound manufactured similarly to the synthesis examples 1-5 is shown in Table 3 thru | or Table 6, this invention is not limited only to these. 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, D1-32a, D1-32b, D1-33a, D1-34a, D1-77c, D1-83b, D1-83c, D1-83d, D1-83e, D1-83f, D1-83g, D1 The structures represented by −100b, D1-100f, D1-101b, D1-101e, D1-101f, D1-105a, D1-105b represent the following structures, and the numbers indicated in the structural formula of D1-32b are , X ¹ represents the substitution position, and the number given in the structural formula of D1-105b represents the substitution position of Z. * 1 represents resinous form. * 2 is resinous and has the same structure but a mixture of two isomers. If the isomer ratio is known, the ratio is listed in Table 6. In the table, “mp” represents “melting point”.

Moreover, the symbol of Table 6 represents the following meaning.
s: singlet, d: doublet, t: triplet, q: quartet, m: multiplet.

[Table 3]

――――――――――――――――――――――――――――――――――――――――
No. R ³ R ^c R ^b mp (℃)
――――――――――――――――――――――――――――――――――――――――
1-001 Me H CH ₂ C (O) NHCH ₂ CF ₃ 202-203
1-002 HH CH ₂ CH = NOMe 153-156
1-003 HHC (= NH) SMe 143-150
1-004 HH CH ₂ CH = NOEt 158-160
1-005 HH CH ₂ CH = NOH 120-122
1-006 H Me CH ₂ CH = NOMe * 2 (2.3: 1)
1-007 HH CH = NOMe 155-156
1-008 Me HC (= NOH) CF ₃ 195-196
1-009 Me H NHC (O) CH ₂ SMe 194-196
1-010 Me H NHC (O) CH (Me) CH ₂ SMe 125-130
1-011 Me H NHC (S) NHCH ₂ CH ₂ CH ₂ SMe 225-227
1-012 Me H NHC (O) NHCH ₂ CH ₂ SEt 124-126
1-013 Me = C (NH ₂ ) OMe 114-115
1-014 Me H CH ₂ CH = NOMe 146-150
1-015 H = CHN (Me) ₂ 140-146
1-016 Me HN = C (Me) ₂ 200-201
1-017 Me HN = CH (Ph) 186-188
1-018 Me HN = C (Me) CH (Me) SMe 140-143
1-019 Me HN = C (Me) CH ₂ CF ₃ 150-154
1-020 Me HN (Me) C (O) CH ₂ SMe 204-206
1-021 Me HN (Me) C (O) CH (Me) CH ₂ SMe * 1
1-022 Me Me N (Me) C (O) CH ₂ SMe * 1
1-023 Me HN (D1-77c) 210-212
1-024 Me HN = CHCH ₂ CF ₃ 216-224
1-025 Me HN = CHCH ₂ SMe * 1
1-026 Me C (O) CH ₃ N = C (Me) CH (Me) SMe * 1
1-027 Me C (O) Bu-t N = C (Me) ₂ * 1
1-028 Me HN = CHMe 179-181
1-029 Cl HN = C (Me) ₂ 177-181
1-030 Me Et N = CH {D1-105b (4-OMe)} 105-108
1-031 HHN = C (Me) ₂ 170-175
1-032 Me HN = CH {D1-105b (4-SMe)} 167-169
1-033 Me D1-83b (Me) 137-139
1-034 Me D1-83b (Et) 121-125
1-035 Me D1-83b (CH ₂ C≡CH) 163-165
1-036 Me D1-83b {CH ₂ C (O) OEt} 148-152
1-037 Me D1-83b (CH ₂ CH = CH ₂ ) 86-89
1-038 Me D1-83b (CH ₂ CN) 139-141
1-039 Me D1-83b (CH ₂ OMe) 142-150
1-040 Me D1-83b (Pr-c) 91-94
1-041 Me D1-83c (Me) 150-170
1-042 Me D1-83c (CH ₂ CH = CH ₂ ) 80-94
1-043 Me D1-83d (CH ₂ CH = CH ₂ ) 147-152
1-044 Me D1-83b (OCH ₂ CH ₂ CF ₃ ) 151-155
1-045 Me H D1-101b 164-166
1-046 Me HN = C (Me) CH (Me) S (O) ₂ Me 214-217
1-047 Me D1-83b (CH ₂ CF ₃ ) 168-170
1-048 Me HC (Me) ₂ C (O) NHCH ₂ CF ₃ 120-125
1-049 Me = C (NH ₂ ) N (Me) ₂ 175-180
1-050 Me HC (= NOMe) NH ₂ 145-150
1-051 Me HC (= NOMe) CH ₂ SMe 124-125
1-052 Me D1-83f (X ^1a = Me, X ^1b = SMe) 163-165
1-053 Me D1-83f (X ^1a = Me, X ^1b = CF ₃ ) 135-137
1-054 Me D1-83g (X ^1a = Me, X ^1b = SMe) 225-233
1-055 Me D1-83e (X ^1a = Me, X ^1b = Me) 61-70
1-056 Me D1-101f (Me) 91-98
1-057 Cl HC (= NOMe) CH ₂ SMe 117-119
1-058 Me D1-83e (X ^1a = Me, X ^1b = Cl) 51-54
1-059 Me = C (NH ₂ ) NHCH ₂ CF ₃ 184-186
1-060 Me H D1-101e (SMe) * 1
1-061 Me HC (= NOMe) CH ₂ S (O) Me 195-197
1-062 Me HC (= NOMe) CH ₂ S (O) ₂ Me 174-175
1-063 Me Me C (= NOMe) CH ₂ SMe * 1
1-064 Me H D1-100b 220-225
1-065 Me = C (NH ₂ ) NHNHC (O) OMe * 1
1-066 Me = C (NH ₂ ) NHNHC (O) Me * 1
1-067 Me H NHS (O) ₂ Me 175-178
1-068 Me H D1-100f (SMe) 210-216
1-069 Me H D1-100f {S (O) ₂ Me} 249-252
1-070 Me HC (= NOMe) CH ₂ SEt 94-96
1-071 Me HC (= NH) CH ₂ SMe 147-149
1-072 Me HC (= NH) CH ₂ SEt 140-142
1-073 HHC (= NOMe) CH ₂ SMe 175-176
1-074 Me = C (NH ₂ ) N (Et) ₂ 102-107
1-075 Me = C (NH ₂ ) N (D1-100a) 183-191
1-076 Me HC (= NH) SEt 124-126
1-077 Me HC (= NH) SPr-n 110-112
1-078 Me HC {= NC (O) Me} SMe 189-194
1-079 Me HC {= NC (O) NHEt} SMe 143-145
1-080 Me D1-83f (X ^1a = Me, X ^1b = D1-33a) 204-206
1-081 Me H CH ₂ C (= NOPr-i) {D1-32b (X ¹ = 3-OMe, 5-Cl)} * 2 (65:35)
1-082 Me HC (= NOMe) CH (Me) CH ₂ SMe 66-71
1-083 Me H CH ₂ C (= NOMe) Me 137-139
1-084 Me HC (= NOMe) CH (Me) SMe * 1
1-085 HH CH (Me) CH = NOMe 112-114
1-086 HHC (= NOMe) CH (Me) CH ₂ SMe 109-110
1-087 Cl HC (= NOMe) CH (Me) CH ₂ SMe 102-103
1-088 Me HC (= NOMe) CH (Me) CH ₂ S (O) Me * 2 (1: 1)
1-089 Me HC (= NOMe) CH (Me) CH ₂ S (O) ₂ Me * 1
1-090 Me HC (= NOMe) CH ₂ CH ₂ SMe 106-107
1-091 Me CH ₂ OMe C (= NOMe) CH (Me) CH ₂ SMe * 1
1-092 Me HC (= NOMe) CH ₂ CH (Me) SMe 116-118
1-093 Me CH ₂ CN C (= NOMe) CH (Me) CH ₂ SMe * 1
――――――――――――――――――――――――――――――――――――――――
[Table 4]

――――――――――――――――――――――――――――――――――――――――
No. A ² R ^c R ^b mp (℃)
――――――――――――――――――――――――――――――――――――――――
2-001 CF HC (= NOMe) CH ₂ SMe 121-122
――――――――――――――――――――――――――――――――――――――――
[Table 5]

――――――――――――――――――――――――――――――――――――――――
No. R ³ R ^c R ^b mp (℃)
――――――――――――――――――――――――――――――――――――――――
3-001 Me HC (= NOMe) CH (Me) CH ₂ SMe * 1
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[Table 6]
―――――――――――――――――――――――――――――――――――――――
No. Proton nuclear magnetic resonance chemical shift value (in CDCl ₃ ): σ (ppm)
―――――――――――――――――――――――――――――――――――――――
1-006;
(Isomer ratio 2.3) 9.02 (brs, 1H), 8.62 (brs, 1H), 8.35-8.50 (m, 1H), 7.95-8.10 (m, 2H) ), 7.40-7.50 (m, 2H), 4.20-4.60 (m, 2H), 3.85-4.00 (m, 3H), 3.24 (brs, 3H)
(Isomer ratio 1) 9.02 (brs, 1H), 8.62 (brs, 1H), 8.35-8.50 (m, 1H), 7.95-8.10 (m, 2H), 7.40-7.50 (m, 2H), 4.20-4.60 (m, 2H), 3.85-4.00 (m, 3H), 3.39 (s, 3H)
1-021;
10.21 (s, 1H), 8.93 (d, J = 2.4 Hz, 1H), 8.66 (s, 1H), 8.54 (dd, J = 4.8, 1.5 Hz, 1H) ), 7.93 (ddd, J = 8.1, 2.4, 1.5 Hz, 1H), 7.40 (dd, J = 8.1, 4.8 Hz, 1H), 3.80-3. 60 (m, 1H), 3.55-3.35 (m, 2H), 2.35 (s, 3H), 2.29 (s, 3H), 2.25-2.05 (m, 2H) , 2.00-1.80 (m, 2H)
1-022;
8.96 (d, J = 2.7 Hz, 1H), 8.60 (d, J = 4.8 Hz, 1H), 8.00 (s, 1H), 7.95-7.90 (m, 1H) ), 7.43 (dd, J = 8.4, 4.8 Hz, 1H), 3.35 (s, 3H), 3.35-3.25 (m, 2H), 3.20 (s, 3H) ), 2.60 (s, 3H), 2.25 (s, 3H)
1-025;
8.97 (d, J = 2.7 Hz, 1H), 8.76 (s, 1H), 8.58 (dd, J = 4.8, 1.5 Hz, 1H), 8.10-8.00 (M, 1H), 7.43 (dd, J = 8.1, 4.8 Hz, 1H), 7.30-7.20 (m, 1H), 3.35 (d, J = 4.8 Hz, 2H), 2.62 (s, 3H), 2.12 (s, 3H)
1-026;
8.98 (d, J = 2.4 Hz, 1H), 8.57 (dd, J = 4.8, 1.5 Hz, 1H), 8.23 (s, 1H), 8.05-8.00 (M, 1H), 7.41 (dd, J = 8.1, 4.8 Hz, 1H), 3.88 (q, J = 7.2 Hz, 1H), 2.56 (s, 3H), 2 .32 (s, 3H), 2.11 (s, 3H), 1.89 (s, 3H), 1.51 (d, J = 7.2 Hz, 3H)
1-027;
8.95-8.90 (m, 1H), 8.83 (s, 1H), 8.60-8.50 (m, 1H), 8.10-8.00 (m, 1H), 7. 45-7.40 (m, 1H), 2.61 (s, 3H), 1.86 (s, 3H), 1.84 (s, 3H), 1.30 (s, 9H)
1-060;
8.93 (d, J = 2.4 Hz, 1H), 8.66 (s, 1H), 8.54 (dd, J = 4.8, 1.5 Hz, 1H), 7.93 (ddd, J = 8.1, 2.4, 1.5 Hz, 1H), 7.40 (dd, J = 8.1, 4.8 Hz, 1H), 4.56 (brs, 1H), 3.80-3. 60 (m, 1H), 3.55-3.35 (m, 2H), 2.35 (s, 3H), 2.29 (s, 3H), 2.25-2.05 (m, 2H) , 2.00-1.80 (m, 2H)
1-065;
9.15-9.10 (m, 1H), 8.70 (s, 1H), 8.60-8.50 (m, 1H), 8.15-8.00 (m, 1H), 7. 50-7.35 (m, 1H), 3.74 (s, 3H), 3.10-2.70 (m, 4H), 2.56 (s, 3H)
1-066;
9.05-8.95 (m, 1H), 8.72 (s, 1H), 8.65-8.50 (m, 1H), 8.15-8.00 (m, 1H), 7. 45-7.30 (m, 1H), 3.00-2.55 (m, 4H), 2.53 (s, 3H), 2.04 (s, 3H)
1-084;
8.97 (d, J = 2.7 Hz, 1H), 8.60 (dd, J = 4.8, 1.5 Hz, 1H), 8.48 (brs, 1H), 8.35 (s, 1H) ), 8.03 (ddd, J = 8.4, 2.7, 1.5 Hz, 1H), 7.43 (dd, J = 8.4, 4.8 Hz, 1H), 4.84 (q, J = 7.2 Hz, 1H), 3.94 (s, 3H), 2.61 (s, 3H), 2.08 (s, 3H), 1.54 (d, J = 7.2 Hz, 3H)
1-088;
(Isomer ratio 1) 8.97 (d, J = 2.7 Hz, 1H), 8.65-8.55 (m, 2H), 8.36 (s, 1H), 8.10-8.00 (M, 1H), 7.42 (dd, J = 8.4, 4.8 Hz, 1H), 4.20-4.05 (m, 1H), 3.89 (s, 3H), 3.35. -3.25 (m, 1H), 2.95-2.75 (m, 1H), 2.65 (s, 3H), 2.58 (s, 3H), 1.42 (d, J = 6) .9Hz, 3H)
(Isomer ratio 1) 8.97 (d, J = 2.7 Hz, 1H), 8.65-8.55 (m, 2H), 8.37 (s, 1H), 8.10-8.00 (M, 1H), 7.42 (dd, J = 8.4, 4.8 Hz, 1H), 4.20-4.05 (m, 1H), 3.89 (s, 3H), 3.35. -3.25 (m, 1H), 2.95-2.75 (m, 1H), 2.64 (s, 3H), 2.58 (s, 3H), 1.45 (d, J = 6) .9Hz, 3H)
1-089;
8.97 (d, J = 2.4 Hz, 1H), 8.65-8.55 (m, 2H), 8.36 (s, 1H), 8.10-8.00 (m, 1H), 7.43 (dd, J = 8.4, 4.8 Hz, 1H), 4.44-4.20 (m, 1H), 3.90 (s, 3H), 3.80 (d, J = 14 .7, 6.6 Hz, 1 H), 3.06 (dd, J = 14.7, 6.9 Hz, 1 H), 2.97 (s, 3 H), 2.59 (s, 3 H), 1.47 (D, J = 7.2Hz, 3H)
1-091;
8.92 (d, J = 2.4 Hz, 1H), 8.56 (dd, J = 4.8, 1.5 Hz, 1H), 8.17 (s, 1H), 8.05-8.00 (M, 1H), 7.45-7.35 (m, 1H), 4.90 (d, J = 4.5 Hz, 2H), 3.89 (s, 3H), 3.45 (s, 3H) ), 2.91 (dd, J = 12.6, 4.5 Hz, 1H), 2.65-2.50 (m, 5H), 1.97 (s, 3H), 1.25 (d, J = 6.6Hz, 3H)
1-093;
8.93 (d, J = 2.1 Hz, 1H), 8.59 (dd, J = 5.1, 1.5 Hz, 1H), 8.05-8.00 (m, 2H), 7.42 (Dd, J = 9.0, 4.8 Hz, 1H), 4.41 (s, 2H), 4.05 (s, 3H), 2.85-2.70 (m, 1H), 2.60 -2.45 (m, 5H), 1.97 (s, 3H), 1.18 (d, J = 6.6 Hz, 3H)
3-001;
9.24 (s, 1H), 8.99 (d, J = 2.1 Hz, 1H), 8.59 (d, J = 3.9 Hz, 1H), 8.45 (s, 1H), 8. 05-8.00 (m, 1H), 7.42 (dd, J = 8.7, 5.1 Hz, 1H), 4.35-4.20 (m, 1H), 3.92 (s, 3H ), 2.96 (dd, J = 13.5, 8.4 Hz, 1H), 2.65-2.55 (m, 4H), 2.12 (s, 3H), 1.36 (d, J = 6.9Hz, 3H)
―――――――――――――――――――――――――――――――――――――――
The proton nuclear magnetic resonance chemical shift values in Table 6 were measured at 300 MHz using Me ₄ Si (tetramethylsilane) as a reference material.
[Test example]
Next, the usefulness of the compound of the present invention as a pest control agent will be specifically described in the following test examples, but the present invention is not limited to these.
Test Example 1 Insecticidal test against brown planthopper A 10% emulsion of the compound of the present invention (depending on the compound, 10% wettable powder) was diluted with water containing a spreading agent to prepare a chemical solution having a concentration of 500 ppm. Rice leaf sheaths are immersed in this chemical solution for about 10 seconds, air-dried and placed in a test tube, and 5 second-instar larvae of the green planthopper (Nilaparvata lugens) are released per test tube and covered with a sponge. Housed in a constant temperature room. The number of dead insects after 6 days was examined, and the death rate (%) (number of dead insects ÷ number of test insects × 100) was calculated. In addition, the test was performed by 2 continuous systems.

As a result, among the compounds tested, the following compounds showed a death rate of 90% or more.
Compounds of the present invention: 1-002 to 1-005, 1-008, 1-010, 1-013 to 1-015, 1-017, 1-020, 1-021, 1-024 to 1-027, 1- 032, 1-034 to 1-079, 1-082 to 1-094, 2-001, 3-001
Test Example 2 Insecticidal test against silver leaf whitefly A moist filter paper was laid on a 7 cm inner diameter styrol cup, and a green leaf cut into 3 cm was placed thereon. A 10% emulsion of a compound of the present invention (depending on the compound, 10% wettable powder) is diluted with water containing a spreading agent to prepare a chemical solution with a concentration of 500 ppm. 2.5 ml was sprayed per styrene cup (2.5 mg / cm 2). After the leaves were air-dried, adults of silver leaf whiteflies (Bemisia argentifolii) were released, covered, and housed in a thermostatic chamber at 25 ° C. The number of dead insects after 5 days was investigated, and the dead insect rate was calculated from the same calculation formula as in Test Example 1. In addition, the test was performed by 2 continuous systems.

As a result, among the compounds tested, the following compounds showed a death rate of 90% or more.
Compounds of the present invention: 1-010, 1-020, 1-026, 1-027, 1-033, 1-034, 1-035, 1-041, 1-049, 1-051, 1-056 to 1- 058, 1-060, 1-061, 1-063, 1-064, 1-067 to 1-1-072, 1-074, 1-077, 1-082 to 1-085, 1-087 to 1- 089, 1-091, 1-093, 1-094, 2-001, 3-001
Test Example 3 Insecticidal test against peach aphid A moist absorbent cotton was laid on a glass petri dish with an inner diameter of 3 cm, and kanran leaves cut out to the same diameter were placed on it, and 4 wormless aphids (Myzus persicae) adult insects did. One day later, a 10% emulsion of the compound of the present invention (depending on the compound, 10% wettable powder) was diluted with water containing a spreading agent to prepare a chemical solution with a concentration of 500 ppm. The chemical solution was sprayed (2.5 mg / cm 2), covered, and stored in a constant temperature room at 25 ° C. The number of dead insects after 6 days was investigated, and the death rate was calculated from the same calculation formula as in Test Example 1. In addition, the test was performed by 2 continuous systems.

As a result, among the compounds tested, the following compounds showed a death rate of 90% or more.
Compounds of the present invention: 1-001 to 1-010, 1-013 to 1-020, 1-022, 1-026 to 1-029, 1-032 to 1-080, 1-082 to 1-094, 2- 001, 3-001
Test Example 4 Insecticidal test against cotton aphids Wet cotton wool with a 3 cm internal diameter petri dish, and a cucumber leaf cut out to the same diameter was placed thereon, and 4 Aphis gossypi adults were released. One day later, a 10% emulsion of the compound of the present invention (depending on the compound, 10% wettable powder) was diluted with water containing a spreading agent to prepare a chemical solution with a concentration of 500 ppm. The chemical solution was sprayed (2.5 mg / cm 2), covered, and stored in a constant temperature room at 25 ° C. The number of dead insects after 6 days was investigated, and the death rate was calculated from the same calculation formula as in Test Example 1. In addition, the test was performed by 2 continuous systems.

As a result, among the compounds tested, the following compounds showed a death rate of 90% or more.
Compounds of the present invention: 1-001, 1-002, 1-004 to 1-008, 1-013, 1-015, 1-018, 1-019, 1-020, 1-026, 1-032, 1- 035-041, 1-044-1-077, 1-080, 1-083 1-094, 2-001, 3-001
Test Example 6 Soil Irrigation Treatment Test for Peach Aphid A 10% emulsion of the compound of the present invention was diluted with tap water to prepare a chemical solution having a concentration of 100 ppm. 10 ml of the chemical solution was irrigated to the stock soil portion of the plastic cup planted cabbage seedling (2.5 true leaf stage) and left in the greenhouse. One day after the irrigation treatment, 20 mosquitoes / strain of adult peach aphid (Myzus persicae) were released and then left in the greenhouse. The number of surviving insects 6 days after the release was examined, and a control value was calculated from the following formula.
Control value (%) = {1- (Cb × Tai) / (Cai × Tb)} × 100
The characters in the formula represent the following:
Cb: number of insects before treatment in the untreated group Cai: number of live insects at the time of final survey in the untreated group Tb: number of insects before treatment in the treated group Tai: number of live insects at the time of final survey in the treated group Among the compounds tested, the following compounds showed a control value of 90% or more.
Compounds of the present invention: 1-001, 1-022, 1-046, 1-051, 1-057, 1-060 to 1-064, 1-070, 1-073, 1-082, 1-084, 1- 085, 1-086, 1-089, 1-090
Test Example 6 Effect test on cat fleas 3.5 mg of the compound of the present invention 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.
Compounds of the present invention: 1-001, 1-003 to 1-006, 1-008, 1-010, 1-012 to 1-015, 1-017 to 1-019, 1-021 to 1-023, 1- 029, 1-031 to 1-037, 1039 to 1-045, 1-047, 1-048, 1-051, 1-052, 1-054, 1-056 to 1-058, 1-060, 1-063, 1-064, 1-067, 1-069 to 1-074, 1-076, 1-078 to 1-085
Test Example 7 Effect test on tick (American dog tick) 3.5 mg of the compound of the present invention 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.
Compounds of the present invention: 1-003, 1-005, 1-010, 1-040

  The novel pyrazole derivative in the present invention exhibits excellent pest control activity, particularly insecticidal / miticidal activity, and is extremely useful with little adverse effect on non-target organisms such as mammals, fish and beneficial insects. A compound.

Claims (9)

Formula (1):

Wherein, ^{A 1} is, -N _{(-O) m2} or represents -CR ^1,
R ¹ , R ³ and R ⁴ are each independently optionally substituted with a hydrogen atom, a halogen atom, cyano, nitro, —OH, —SH, —NH ₂ , C ₁ -C ₆ alkyl, R ^28a ( C ₁ -C ₆ ) alkyl, C ₃ -C ₈ cycloalkyl, optionally substituted with R ^28a (C ₃ -C ₈ ) cycloalkyl, C ₂ -C ₆ alkenyl, optionally substituted with R ^28a ( C ₂ -C _{6) alkenyl,} C 3 -C ₈ ^{cycloalkenyl,} substituted optionally substituted with ^{R 28a} _(C 3 ~C _{8) cycloalkenyl,} C 2 -C ₆ ^alkynyl, optionally with ^{R 28a} ( C ₂ -C _{6) alkynyl,} 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,} C 1 -C _{6 alkylcarbonyl,} C 3 -C _{8 cycloalkylcarbonyl,} C 1 -C _{6 haloalkylcarbonyl,} C 3 -C ₈ halocycloalkylcarbonyl, 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 alkyl Represents amino or di (C ₁ -C ₆ alkyl) amino;
R ² is a halogen atom, cyano, nitro, —OH, —SH, —NH ₂ , C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted with R ^28a , C ₃ -C _8. ^cycloalkyl, substituted optionally substituted with ^{R 28a} _(C 3 ~C _{8) cycloalkyl,} C 2 -C ₆ ^alkenyl, optionally with ^{R 28a} _(C 2 ~C _{6) alkenyl,} C 3 -C ₈ ^{cycloalkenyl,} optionally substituted with ^{R 28a} _(C 3 ~C _{8) cycloalkenyl,} C 2 -C ₆ ^alkynyl, which is optionally substituted with ^{R 28a} _(C 2 ~C _{6) alkynyl,} 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 ha B _{alkylsulfinyl,} C 1 -C _{6 haloalkylsulfonyl,} C 1 -C _{6 alkylcarbonyl,} C 3 -C _{8 cycloalkylcarbonyl,} C 1 -C _{6 haloalkylcarbonyl,} C 3 -C ₈ halocycloalkyl _{carbonyl, 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 or di _(C 1 -C ₆ Alkyl) amino, and when n represents an integer of 2 or more, each R ² may be the same as or different from each other,
R ^a represents —C (O) N (R ^b ) R ^c or —C (S) N (R ^b ) R ^c ,
R ^b is (C ₁ -C ₁₂ ) alkyl optionally substituted with R ^5a , -C (R ⁷ ) = NOH, -C (R ⁷ ) = NOR ⁶ , -C (= NOR ⁶ ) OR ^6a , ^{-C (= NOR 6) SR 6a} , -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, represents ^{-C (R 7) = NR 8b} , -N (R 8g) R 8 or ^{-N = C (R 7a) R} 7b,
R ^c is hydrogen _atom, 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, optionally substituted with ^{R 5} _(C 2 _{~C 12) ^{alkynyl, -OR 6c, -S (O)}} r2 R 6c, -C (O) R ^{7c, -C (O) OR 6a} , -C (O) SR 6a, -C (S) OR 6a, -C (S) SR 6a, -N (R 8a) R 8, -C (O) N ( ^{R 8a) R 8 -C (S} ) N (R 8a) R 8, -S (O) _{^{r2 N (R 8a) R 8}} , phenyl, or represents _(Z) phenyl substituted with _q, naphthyl, _(Z) naphthyl substituted with _q or D1-1～D1-94, or, ^{R c} is R together with ^b may form ═C (R ^8c ) R ^8d ,
R ⁵ is a halogen atom, cyano, nitro, C ₃ -C ₈ cycloalkyl, —OH, —OR ¹¹ , —SH, —S (O) _{r 2} R ¹¹ , —C (O) R ¹² , —C (O ) OR ^11a , -C (O) SR ^11a , -C (S) OR ^11a , -C (S) SR ^11a , -N (R ^13a ) R ¹³ , -C (O) N (R ^13a ) R ¹³ , _{^{-C (S) N (R 13a}} ) R 13, -S (O) r2 N (R 13a) R 13, -C (R 12) = NOH, -C (R 12) = NOR 11, phenyl, (Z ) phenyl substituted with _q, represents naphthyl, the naphthyl or D1-1~D1-94 substituted with _{(Z) q,}
R ^5a represents —C (R ¹² ) = NOH, —C (R ¹² ) = NOR ¹¹ or —C (O) N (R ¹³ ) R ^13f ,
R ⁶ , R ^6a and R ^6c are each independently C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted with R ¹⁴ , C ₃ -C ₈ cycloalkyl, optional with R ¹⁴ substituted in _(C 3 ~C _{8) cycloalkyl,} C 2 -C ₆ ^alkenyl, optionally substituted with ^{R 14} _(C 2 ~C _{6) alkenyl,} C 3 -C ₈ ^{cycloalkenyl,} optionally ^{R 14} (C ₃ -C ₈ ) cycloalkenyl, C ₂ -C ₆ alkynyl, (C ₂ -C ₆ ) alkynyl optionally substituted with R ¹⁴ , —S (O) _r R ¹¹ , —C ( ^{O) R 12, -C (O} ) OR 11, -C (O) SR 11, -C (S) OR 11, -C (S) SR 11, -C (O) N (R 13a) R 13 - ^{C (S) N (R 13a} ) R 13, -S (O) r2 N (R 13a ) R ¹³ , phenyl, (Z) _q- substituted phenyl, naphthyl, (Z) _q- substituted naphthyl or D1-1 to D1-94,
R ⁷ , R ^7a and R ^7c are each independently a hydrogen atom, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted with R ¹⁴ , C ₃ -C ₈ cycloalkyl, R optionally substituted with ¹⁴ _(C 3 ~C _{8) cycloalkyl,} C 2 -C ₆ ^alkenyl, optionally substituted with ^{R 14} _(C 2 ~C _{6) alkenyl,} C 3 -C ₈ cycloalkenyl, R optionally substituted with ¹⁴ _(C 3 ~C _{8) cycloalkenyl,} optionally substituted with C 2 -C _{6 ^{alkynyl, R 14 (C 2 ~C 6}} ) ^alkynyl, -OR ^11, -S (O) _{^{r R 11, -C (O)}} R 12, -C (O) OR 11, -C (O) SR 11, -C (S) OR 11, -C (S) SR 11, -C (O) N ^{(R 13a) R 13 -C (} S) N (R 13a) R 13, -S _{^{O) r2 N (R 13a)}} R 13, represents phenyl, _(Z) phenyl substituted with _q, naphthyl, naphthyl or substituted with _{(Z) q} D1-1～D1-94,
R ^7b is a hydrogen _atom, C 1 -C ₆ ^alkyl, optionally substituted with ^{R 14} _(C 1 ~C _{6) alkyl,} C 3 -C ₈ ^cycloalkyl, optionally substituted with ^{R 14} _{(C 3} -C _{8) cycloalkyl,} C 2 -C ₆ ^alkenyl, optionally substituted with ^{R 14} _(C 2 ~C _{6) alkenyl,} C 3 -C ₈ ^{cycloalkenyl,} optionally substituted with ^{R 14} _{(C 3} -C _{8) cycloalkenyl,} C 2 -C ₆ ^alkynyl, optionally substituted with ^{R 14} _(C 2 ~C ₆₎ alkynyl, phenyl, phenyl substituted with _{(Z) q,} naphthyl, with _{(Z) q} Represents substituted naphthyl or D1-1 to D1-94, or R ^7b and R ^7a together form a C _{3 to} C ₆ alkylene chain or a C _{3 to} C ₆ alkenylene chain to form R ^7b and ^{R 7} There may form a 4 to 7 membered ring with the carbon atoms to which they are attached alkylene chain or alkenylene chain this time, an oxygen atom, it may contain one to three sulfur atom or a nitrogen atom, and a halogen atom, a cyano group , A nitro group, a C ₁ -C ₆ alkyl group, a (C ₁ -C ₆ ) alkyl optionally substituted with R ¹⁴ , optionally —OR ¹⁵ , —S (O) _r R ¹⁵ , an oxo group or a thioxo group May be replaced,
R ⁸ and R ^8a are each independently a hydrogen atom, cyano, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted with R ¹⁴ , C ₃ -C ₈ cycloalkyl, R ^14. optionally substituted _(C 3 ~C _{8) cycloalkyl,} C 2 -C ₆ ^alkenyl, optionally substituted with ^{R 14} _(C 2 ~C _{6) alkenyl,} C 3 -C ₈ cycloalkenyl ^{in, R 14} (C ₃ -C ₈ ) cycloalkenyl, C ₂ -C ₆ alkynyl, (C ₂ -C ₆ ) alkynyl optionally substituted with R ¹⁴ , —OR ¹¹ , —S (O) _r R ¹¹ , —C (O) R ¹² , —C (O) OR ¹¹ , —C (O) SR ¹¹ , —C (S) OR ¹¹ , —C (S) SR ¹¹ , —C (O) N ( ^{R 13a) R 13, -C (} S) N (R 13a) R 13, -S _{^{O) r2 N (R 13a)}} R 13, phenyl, or represents _(Z) phenyl substituted with _q, naphthyl, naphthyl or substituted with _{(Z) q} D1-1～D1-94, or, ^{R 8} May form a C ₂ -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, in which case the alkylene chain May contain one oxygen, sulfur or nitrogen atom, and is optionally substituted with a halogen atom, cyano, C ₁ -C ₆ alkyl, R ¹⁴ (C ₁ -C ₆ ) alkyl, phenyl, (Z ) Optionally substituted by a phenyl, oxo or thioxo group substituted by _q , or R ⁸ together with R ^8a may form ═C (R ^8c ) R ^8d ,
R ^8b is hydrogen, _cyano, C 1 -C ₆ ^alkyl, optionally substituted with ^{R 14} _(C 1 ~C _{6) alkyl,} substituted C 3 -C ₈ ^cycloalkyl, optionally with ^{R 14} ( C ₃ -C _{8) cycloalkyl,} C 2 -C ₆ ^alkenyl, optionally substituted with ^{R 14} _(C 2 ~C _{6) alkenyl,} C 3 -C ₈ ^{cycloalkenyl,} optionally substituted with ^{R 14} ( C ₃ -C _{8) cycloalkenyl,} C 2 -C ₆ ^alkynyl, optionally substituted with ^{R 14} _(C 2 ~C _{6) ^{alkynyl, -OR 11, -S (O)}} r R 11, -C (O ^{) R 12, -C (O)} OR 11, -C (O) SR 11, -C (S) OR 11, -C (S) SR 11, -C (O) N (R 13a) R 13, - ^{C (S) N (R 13a} ) R 13, -S (O) r N (R 13 ) ^{R 13,} represents phenyl, _(Z) phenyl substituted with _q, naphthyl, naphthyl or substituted with _{(Z) q} D1-1～D1-94,
R ^8g represents —C (O) R ^12a , —C (O) N (R ^13f ) R ¹³ , —C (S) N (R ^13f ) R ¹³ or —S (O) _r R ¹¹ ,
R ^8c represents a hydrogen atom, —OR ¹¹ , —S (O) _r R ¹¹ , —N (R ^13a ) R ¹³ or —N (R ^13c ) N (R ^13a ) R ¹³ ;
R ^8d is a hydrogen atom, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted with R ¹⁴ , —OR ^11b , —S (O) _r R ^11b or —N (R ^13e ). R ^13d represents or, alternatively, R ^8d and R ^8c together form a C ₄ -C ₆ alkylene chain or a C ₄ -C ₆ alkenylene chain, so that together with the carbon atom to which R ^8d and R ^8c are attached A 5- to 7-membered ring may be formed, and 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 ) alkyl optionally substituted with R ¹⁴ , C ₃ -C ₈ cycloalkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, -OR ¹⁵ ,- S _{(O) r} ^15, phenyl, _(Z) phenyl substituted with _q, naphthyl, _(Z) naphthyl substituted with _q, D1-1～D1-94, may be optionally substituted by oxo or thioxo group,
R ¹¹ , R ^11a and R ^11b are each independently C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted with R ^14a , C ₂ -C ₆ alkenyl, optionally with R ^14a substituted _(C 2 ~C _{6) alkenyl,} C 3 -C ₈ ^{cycloalkenyl,} optionally substituted with ^{R 14a} _(C 3 ~C _{8) cycloalkenyl,} C 2 -C ₆ ^alkynyl, optionally with ^{R 14a} substituted _(C 2 ~C _{6) alkynyl,} C 3 -C ₈ ^cycloalkyl, optionally substituted with ^{R 14a} _(C 3 ~C ₈₎ cycloalkyl, phenyl, phenyl substituted with _{(Z) q,} Naphthyl, (Z) naphthyl substituted with _q or D1-1 to D1-94,
R ¹² is a hydrogen _atom, C 1 -C ₆ ^alkyl, optionally substituted with ^{R 14a} _(C 1 ~C _{6) alkyl,} C 2 -C ₆ ^alkenyl, optionally substituted with ^{R 14a} _(C 2 ~ C _{6) alkenyl,} C 3 -C ₈ ^{cycloalkenyl,} optionally substituted with ^{R 14a} _(C 3 ~C _{8) cycloalkenyl,} optionally substituted with C 2 -C ₆ ^{alkynyl, R 14a} _(C 2 ~ C ₆ ) alkynyl, C ₃ -C ₈ cycloalkyl, (C ₃ -C ₈ ) cycloalkyl optionally substituted with R ^14a , phenyl, (Z) _q substituted phenyl, naphthyl, (Z) _q Represents substituted naphthyl or D1-1 to D1-94;
R ¹³ , R ^13c , R ^13d and R ^13e each independently represent a hydrogen atom or R ^11a ,
R ^12a represents (C ₁ -C ₆ ) alkyl optionally substituted with R ^14a , or R ^12a together with R ⁸ is a C ₂ -C ₆ alkylene chain or C ₂ -C ₆ By forming an alkenylene chain, a 4- to 8-membered ring may be formed together with the carbon atom to which R ^12a is bonded and the nitrogen atom to which R ⁸ is bonded. At this time, the alkylene chain or alkenylene chain is an oxygen atom, a sulfur atom Alternatively, it may contain 1 or 2 nitrogen atoms and is a halogen atom, cyano, nitro, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted with R ^14a , —OH, —OR ¹⁵ , —SH, —S (O) _r R ¹⁵ , an oxo group or a thioxo group,
R ^13a represents a hydrogen atom, R ^11a , —C (O) OR ^15a or —C (O) R ¹⁶ , or R ^13a together with R ¹³ represents a C _{2 to} C ₇ alkylene chain. Forming a 3- to 8-membered ring together with the nitrogen atom to which R ^13a and R ¹³ are bonded, wherein the alkylene chain may contain one oxygen, sulfur or nitrogen atom, and A halogen atom, cyano, nitro, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted with R ^14a , —OH, —OR ¹⁵ , —SH, —S (O) _r R ¹⁵ , Optionally substituted by an oxo or thioxo group,
R ^13f represents (C ₁ -C ₆ ) alkyl optionally substituted with R ^14a ,
R ¹⁴ and R ^14a are each independently a halogen atom, cyano, nitro, C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ halocycloalkyl, —OH, —OR ¹⁵ , —SH, —S (O). _{^{r R 15, -N (R 17a}} ) R 17, -C (O) OH, -C (O) OR 15a, -CHO, -C (O) R 16, -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) r2 N (R 17a) R ¹⁷ , phenyl, phenyl substituted with (Z) _q , naphthyl, naphthyl substituted with (Z) _q or D1-1 to D1-94,
R ¹⁵ , R ^15a and R ¹⁶ are each independently C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₃ -C ₈ cycloalkyl or It represents C ₃ -C ₈ cycloalkenyl,
R ¹⁷ and R ^17a 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, C ₃ -C ₈ cycloalkyl or It represents C ₃ -C ₈ cycloalkenyl,
D1-1 to D1-94 each represent a ring represented by the following structural formula;



X ¹ is a halogen atom, cyano, nitro, —OH, —SH, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted with R ²⁸ , C ₂ -C ₆ alkenyl, R ^28. (C ₂ -C ₆ ) alkenyl optionally substituted with, C ₃ -C ₈ cycloalkenyl, (C ₃ -C ₈ ) cycloalkenyl optionally substituted with R ²⁸ , C ₂ -C ₆ alkynyl, R ²⁸ optionally substituted in _(C 2 ~C _{6) alkynyl,} C 3 -C ₈ ^cycloalkyl, optionally substituted with ^{R 28} _(C 3 ~C ₈₎ ^cycloalkyl, -OR ^25, -S (O) _{^{r R 25, -C (O)}} OH, -C (O) OR 25a, -C (O) R 26, -C (O) N (R 27a) R 27, -C (S) N (R 27a) R ²⁷ , —N (R ^27a ) R ²⁷ , —C (= NOR ^{25 _{) R 26, -S (O)}} 2 N (R 27a) R 27, ^phenyl, (Z ₂₎ phenyl substituted with _q2, ^naphthyl, (Z ₂₎ is substituted with _q2 naphthyl or D2-1~D2- 41, and when g1, g2, or g4 represents an integer of 2 or more, each X ¹ may be the same as or different from each other, and when two X ¹ are adjacent, adjacent to each other The two X ¹ groups represented by —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 it may be each of X ¹ to form a 5- or 6-membered ring with the carbon atoms to which they are attached hydrogen atoms bonded to the time each of the carbon atoms forming the ring, 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 alkylsulfinyl group or a _C 1 -C ₆ alkylsulfonyl group Optionally substituted by
X ^1a represents a hydrogen atom, cyano, _-OH, optionally substituted with C 1 -C ₆ ^alkyl, optionally substituted with ^{R 28} _(C 1 ~C _{6) alkyl,} C 2 -C ₆ ^{alkenyl, R 28} and _(C 2 ~C _{6) alkenyl,} C 3 -C ₈ ^{cycloalkenyl,} substituted optionally substituted with ^{R 28} _(C 3 ~C _{8) cycloalkenyl,} optionally with C 2 -C ₆ ^{alkynyl, R 28} (C ₂ -C ₆ ) alkynyl, C ₃ -C ₈ cycloalkyl, (C ₃ -C ₈ ) cycloalkyl optionally substituted with R ²⁸ , —OR ²⁵ , —S (O) _r R ²⁵ , — C (O) OH, —C (O) OR ^25a , —C (O) R ²⁶ , —C (O) N (R ^27a ) R ²⁷ , —C (S) N (R ^27a ) R ²⁷ , —N ^{(R 27a) R 27, -C} (= NOR 25) R 26, -S ( _{^{) 2 N (R 27a) R}} 27, represents ^phenyl, (Z ₂₎ phenyl substituted with _q2, ^naphthyl, (Z ₂₎ naphthyl or D2-1~D2-41 substituted with _q2,
X ^1b is a halogen atom, cyano, nitro, —OH, —SH, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted with R ²⁸ , C ₂ -C ₆ alkenyl, R ^28. (C ₂ -C ₆ ) alkenyl optionally substituted with, C ₃ -C ₈ cycloalkenyl, (C ₃ -C ₈ ) cycloalkenyl optionally substituted with R ²⁸ , C ₂ -C ₆ alkynyl, R ²⁸ optionally substituted in _(C 2 ~C _{6) alkynyl,} C 3 -C ₈ ^cycloalkyl, optionally substituted with ^{R 28} _(C 3 ~C ₈₎ ^cycloalkyl, -OR ^25, -S (O) _{^{r R 25, -C (O)}} OH, -C (O) OR 25a, -C (O) R 26, -C (O) N (R 27a) R 27, -C (S) N (R 27a) R ²⁷ , —N (R ^27a ) R ²⁷ , —C (= NOR ^{2 _{5) R 26, -S (O}} ) 2 N (R 27a) R 27, ^phenyl, (Z ₂₎ phenyl substituted with _q2, ^naphthyl, (Z ₂₎ is substituted with _q2 naphthyl or D2-1~D2 -41, and when f1, f2, f4, f5, f6, f7, f8 or f9 represents an integer of 2 or more, each X ^1b may be the same as or different from each other; When two X ^1b are substituted on the same carbon, the two X ^1b together are oxo, thioxo, imino, C ₁ -C ₆ alkylimino, C ₁ -C ₆ alkoxyimino or C _1- C ₆ alkylidene may be formed,
Z is a halogen atom, cyano, nitro, —OH, —SH, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted with R ²⁸ , C ₂ -C ₆ alkenyl, R ²⁸ optionally substituted _(C 2 ~C _{6) alkenyl,} C 3 -C ₈ ^{cycloalkenyl,} optionally substituted with ^{R 28} _(C 3 ~C _{8) cycloalkenyl,} with C 2 -C ₆ ^{alkynyl, R 28} optionally substituted _(C 2 ~C _{6) alkynyl,} C 3 -C ₈ ^cycloalkyl, optionally substituted with ^{R 28} _(C 3 ~C _{8) ^{cycloalkyl, -OR 25, -S (O)}} r R ²⁵ , —C (O) OH, —C (O) OR ^25a , —C (O) R ²⁶ , —C (O) N (R ^27a ) R ²⁷ , —C (S) N (R ^27a ) R ^{27, -N (R 27a) R} 27, -C (= NOR 25) _{^{R 26, -S (O) 2}} N (R 27a) R 27, ^phenyl, (Z ₂₎ phenyl substituted with _q2, ^naphthyl, (Z ₂₎ is substituted with _q2 naphthyl or D2-1~D2-41 When q represents an integer of 2 or more, each Z may be the same as or different from each other, and when two Zs are adjacent to each other, the two adjacent Zs are − _{CH 2 CH 2 CH 2 -,} - CH 2 CH 2 O -, - CH 2 OCH 2 -, - OCH 2 O -, - CH 2 CH 2 S -, - CH 2 SCH 2 -, - 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 by forming a -OCH ₂ CH ₂ S-, its A 5-membered ring or a 6-membered ring may be formed together with the carbon atom to which each Z is bonded. At this time, the hydrogen atom bonded to each carbon atom forming the ring is a halogen atom, C _{1 to} C _6. alkyl _group, C 1 -C ₆ haloalkyl _group, C 1 -C ₆ alkoxy _group, C 1 -C ₆ alkylthio _group, optionally substituted by C 1 -C ₆ alkylsulfinyl group or a _C 1 -C ₆ alkylsulfonyl group Well,
R ²⁵ , R ^25a and R ²⁶ each independently represent C ₁ -C ₆ alkyl or (C ₁ -C ₆ ) alkyl optionally substituted with R ^32a ,
R ²⁷ and ^{R 27a} represent independently a hydrogen _atom, C 1 -C ₆ alkyl, -S _(O) ^{r R 34} or -C ^{(O) R 34,}
R ²⁸ and R ^28a each independently represent a halogen atom, —OH, —OR ²⁹ , —SH or —S (O) _r R ²⁹ ;
R ²⁹ and R ³³ each independently represent C ₁ -C ₆ alkyl;
R ³² and R ^32a each independently represent a halogen atom, —OR ³³ or —S (O) _r R ³³ ;
R ³⁴ represents C ₁ -C ₆ alkyl, C ₃ -C ₈ cycloalkyl or C ₁ -C ₆ haloalkyl,
D2-1 to D2-41 each represent a ring represented by the following structural formula;


X ² is a halogen atom, cyano, nitro, —OH, —SH, 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 1 -C _{6 alkoxy,} C 1 -C _{6 haloalkoxy,} C 1 -C ₆ alkylthio, C ₁ -C _{6 haloalkylthio,} C 1 -C ₆ alkylsulfinyl represents _Le, C 1 -C _{6 haloalkylsulfinyl,} a C 1 -C ₆ alkylsulfonyl or _C 1 -C ₆ haloalkylsulfonyl, t1, t2 or t4 is 2 or more Each X ² may be the same as or different from each other,
X ^2a is 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,} represents C 3 -C ₈ halocycloalkyl,
Z ² is a halogen atom, cyano, nitro, —OH, —SH, 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 1 -C _{6 alkoxy,} C 1 -C _{6 haloalkoxy,} C 1 -C ₆ alkylthio, C ₁ -C ₆ represents _{haloalkylthio,} C 1 -C _{6 alkylsulfinyl,} C 1 -C _{6 haloalkylsulfinyl,} a C 1 -C ₆ alkylsulfonyl or _C 1 -C ₆ haloalkylsulfonyl, q2 is an integer of 2 or more Each Z may be the same as or different from each other;
n, g1, f1, and t1 each independently represents an integer of 0 to 3,
g2 and t2 each independently represent an integer of 0 to 2,
g3 and t3 each independently represent an integer of 0 to 1,
g4, f4 and t4 each independently represent an integer of 0 to 4,
f5 represents an integer of 0 to 5,
f6 represents an integer of 0 to 6,
f7 represents an integer of 0 to 7,
f8 represents an integer of 0 to 8,
f9 represents an integer of 0 to 9,
q and q2 each independently represent an integer of 1 to 5,
m1, m2 and m4 each independently represents an integer of 0 or 1,
r and r2 each independently represents an integer of 0 to 2; ] The pyrazole derivative represented by these, or its salt. A ¹ represents -CR ¹
R ¹ , R ³ and R ⁴ each independently represents a hydrogen atom, a halogen atom or C ₁ -C ₆ alkyl;
The pyrazole derivative or a salt thereof according to claim ₁ , wherein R ² represents a halogen atom or C ₁ -C ₆ alkyl. R ¹ represents a hydrogen atom or a halogen atom,
R ³ represents a hydrogen atom, a halogen atom or C ₁ -C ₆ alkyl,
R ⁴ represents a hydrogen atom,
R ^b is (C ₁ -C ₆ ) alkyl optionally substituted with R ^5a , -C (R ⁷ ) = NOH, -C (R ⁷ ) = NOR ⁶ , -C (R ⁷ ) = NR ^8b , -C ^{(= NOR 6)} represents ^{N (R 8a) R 8,} -C (= NR 8b) SR 6a, -N (R 8g) R 8 or ^{-N = C (R 7a) R} 7b,
R ^c represents a hydrogen atom, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted with R ⁵ or —C (O) R ^7c , or R ^c represents R ^b Together, they may form ═C (R ^8c ) R ^8d ,
R ⁵ represents cyano or —OR ¹¹ ;
R ⁶ , R ^6a , R ^7c , R ¹¹ , R ^15a and R ¹⁶ each independently represent C ₁ -C ₆ alkyl;
R ⁷ represents a hydrogen atom, C ₁ -C ₆ alkyl or (C ₁ -C ₆ ) alkyl optionally substituted with R ¹⁴ ,
R ^7a represents C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted with R ¹⁴ , phenyl or phenyl substituted with (Z) _q ;
R ^7b represents a hydrogen atom or C ₁ -C ₆ alkyl, or R ^7b together with R ^7a forms a C ₄ alkylene chain, whereby the carbon atom to which R ^7b and R ^7a are bonded. Together with this, the alkylene chain may contain one sulfur atom,
R ⁸ represents a hydrogen atom or C ₁ -C ₆ alkyl,
R ^8a represents a hydrogen atom,
R ^8b represents a hydrogen atom, —C (O) R ¹² or —C (O) N (R ^13a ) R ¹³ ;
R ^8c represents —OR ¹¹ , —N (R ^13a ) R ^13, or —N (R ^13c ) N (R ^13a ) R ¹³ ;
R ^8d may represent a hydrogen atom or ^{-N (R 13e)} R ^{13d, or, R 8d} may be form an alkylene chain, or alkenylene chain of _{C 4} or _{C 5 C 4} to together with ^{R 8c} May form a 5- or 6-membered ring together with the carbon atom to which R ^8d and R ^8c are bonded, and this alkylene chain or alkenylene chain may contain 1 to 3 sulfur atoms or nitrogen atoms, and halogen Atom, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted with R ¹⁴ , C ₃ -C ₈ cycloalkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, -OR ¹⁵ , optionally substituted by —S (O) _r R ¹⁵ or D1-33,
R ¹² represents a hydrogen atom, C ₁ -C ₆ alkyl or D1-32;
R ^13c , R ^13d and R ^13e represent a hydrogen atom and R ^12a represents (C ₁ -C ₆ ) alkyl optionally substituted with R ^14a , or R ^12a together with R ⁸ By forming an alkylene chain of C _{3 to} C _4, a 5- to 6-membered ring may be formed together with the carbon atom to which R ^12a is bonded and the nitrogen atom to which R ⁸ is bonded, and —S (O) _r R Optionally substituted by ¹⁵ ;
R ¹³ represents a hydrogen atom, C ₁ -C ₆ alkyl or (C ₁ -C ₆ ) alkyl optionally substituted with R ^14a ,
R ^13a represents a hydrogen atom, C ₁ -C ₆ alkyl, —C (O) OR ^15a or —C (O) R ¹⁶ , or R ^13a together with R ¹³ is a C ₄ alkylene chain. To form a 5-membered ring together with the nitrogen atom to which R ^13a and R ¹³ are bonded,
R ¹⁴ represents a halogen atom, _{^{cyano, -OR 15, -S (O)}} r R 15 or -C a ^{(O) OR 15a,}
R ^14a represents a halogen atom or —S (O) _r R ¹⁵ ;
R ¹⁵ represents C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
X ¹ represents a halogen atom or C ₁ -C ₆ alkoxy;
Z _is, C 1 -C ₆ alkoxy or _C 1 -C ₆ alkylthio,
g4 represents an integer of 2;
q represents an integer of 1;
n, m1 and m3 represent 0;
The pyrazole derivative or a salt thereof according to claim 2, wherein r represents an integer of 0 to 2.   The pest control agent which contains the 1 type (s) or 2 or more types chosen from the pyrazole derivative and its salt of Claims 1-3 as an active ingredient.   An agrochemical containing one or more selected from the pyrazole derivatives according to claim 1 and a salt thereof as an active ingredient.   An internal or ectoparasite control agent for mammals or birds containing one or more selected from the pyrazole derivatives and salts thereof according to claim 1 as active ingredients.   An insecticide or acaricide containing, as an active ingredient, one or more selected from the pyrazole derivatives and salts thereof according to claim 1.   The soil treatment agent which contains 1 type, or 2 or more types chosen from the pyrazole derivative and its salt of Claims 1-3 as an active ingredient.   The soil treatment agent according to claim 8, wherein the soil treatment method is soil irrigation treatment.