JP2015003895A - Thiazole derivative and pest control agent - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide novel pest control agents, in particular insecticides or miticides.SOLUTION: This invention provides thiazole derivatives and pest control agents represented by formula (1) where Arepresents -N(O)or -CR, Rand Rindependently represent a hydrogen atom, a halogen atom, C-Calkyl or the like, Rrepresents C-Calkynyl or the like, Rrepresents -C(O)Ror the like, Rrepresents C-Calkyl or the like, and m1 represents an integer of 0 or 1.

Description

  The present invention relates to a novel thiazole derivative and a salt thereof, and a pest control agent comprising 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.

  For example, Patent Documents 3 and 4 disclose certain thiazole derivatives, but neither suggest nor disclose that they have insecticidal activity.

  Patent Documents 1 and 2 disclose that thiazole derivatives are useful as insecticides, but do not disclose any thiazole derivatives according to the present invention.

International Publication No. 2011/128304 International Publication No. 2010/129497 International Publication No. 2008/090382 Japanese Patent Application Publication No. 2003/212864

  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 thiazole derivative represented by the following formula (1) according to the present invention has excellent pest control activity, particularly insecticide / miticide. The present invention has been completed by finding it to be an extremely useful compound that exhibits activity and has almost no adverse effects on non-target organisms such as mammals, fish and beneficial insects.

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

[1]
Formula (1):

Wherein, ^{A 1} is, -N _{(-O) m2} or represents -CR ^1,
R ¹ and R ³ each independently represent a hydrogen atom, a halogen atom, cyano, nitro, —OH, —SH, —NH ₂ , —CHO, —C (O) OH, —C (O) NH ₂ , — _{C (S) NH 2, -S} (O) 2 NH 2, C 1 ~C 6 ^alkyl, optionally substituted by ^{R 28a} _(C 1 ~C _{6) alkyl,} C 3 -C ₈ ^{cycloalkyl, R 28a} (C ₃ -C ₈ ) cycloalkyl, C ₂ -C ₆ alkenyl, optionally substituted by R ^28a (C ₂ -C ₆ ) alkenyl, C ₃ -C ₈ cycloalkenyl, R ^28a optionally substituted by _(C 3 ~C _{8) cycloalkenyl,} C 2 -C ₆ ^alkynyl, optionally substituted by ^{R 28a} _(C 2 ~C _{6) alkynyl,} C 1 -C _{6 alkoxy, C} 1 ~ C ₆ halo _Alkoxy, 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 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 alkylaminocarbonyl, di _(C 1 -C ₆ alkyl) _{aminocarbonyl,} C 1 -C ₆ alkylamino , di _(C 1 -C ₆ alkyl) amino, phenyl, (Z) phenyl substituted by _q , naphthyl, (Z) naphthyl substituted by _q , D1-32, D1-33, D1-34, D1-35, D1-36, D1-37, D1-38, D1-39 , D1-79, D1-80, D1-81, D1-82, D1-84, D1-85, D1-87, D1-92, D1-93, D1-95, D1-96 or D1-98 ,
R ² is a halogen atom, cyano, nitro, —OH, —SH, —NH ₂ , —CHO, —C (O) OH, —C (O) NH ₂ , —C (S) NH ₂ , —S ( _{O) 2 NH 2, C 1} ~C 6 ^alkyl, optionally substituted by ^{R 28a} _(C 1 ~C _{6) alkyl,} optionally substituted by C 3 -C ₈ ^{cycloalkyl, R 28a} _(C 3 ~ C _{8) cycloalkyl,} C 2 -C ₆ ^alkenyl, optionally substituted by ^{R 28a} _(C 2 ~C _{6) alkenyl,} C 3 -C ₈ ^{cycloalkenyl,} optionally substituted by ^{R 28a} _(C 3 ~ C _{8) cycloalkenyl,} C 2 -C ₆ ^alkynyl, optionally substituted by ^{R 28a} _(C 2 ~C _{6) alkynyl,} C 1 -C _{6 alkoxy,} C 1 -C _{6 haloalkoxy,} C 1 -C ₆ Alkyl _Thio, 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 halocycloalkyl _carbonyl, C 1 -C _{6 alkoxycarbonyl,} C 1 -C _{6 haloalkoxycarbonyl,} C 1 -C ₆ alkyl Aminosulfonyl, di (C ₁ -C ₆ alkyl) aminosulfonyl, C ₁ -C ₆ alkylaminocarbonyl, di (C ₁ -C ₆ alkyl) aminocarbonyl, C ₁ -C ₆ alkylamino, di (C ₁ -C ₆ alkyl) amino, phenyl, phenyl substituted by _{(Z) q,} Fuchiru, naphthyl substituted by _{(Z) q, D1-32, D1-33} , D1-34, D1-35, D1-36, D1-37, D1-38, D1-39, D1-79, D1- 80, D1-81, D1-82, D1-84, D1-85, D1-87, D1-92, D1-93, D1-95, D1-96 or D1-98, n is an integer of 2 or more Each R ² may be the same as or different from each other;
R ^{a is} optionally substituted by optionally substituted by ^{R 5a} _(C 1 ~C _{6) alkyl,} C 2 -C ₆ alkynyl, or ^{R 5b} _(C 2 ~C ₆₎ alkynyl,
R ^b is —C (O) OR ^6a , —C (O) R ⁷ , —C (S) R ⁷ , —C (O) N (R ⁸ ) R ^8a or —C (S) N (R ⁸ ) ^Represents R ^8a
R ^5a represents —OR ¹¹ or —S (O) _r R ¹¹ ,
R ^5b is a halogen atom, —OR ¹¹ or —S (O) _r R ^11.
R ^6a represents C ₁ -C ₆ alkyl or (C ₁ -C ₆ ) alkyl optionally substituted with R ¹⁴ ;
R ⁷ is a hydrogen _atom, C 1 -C ₆ ^alkyl, optionally substituted by ^{R 14} _(C 1 ~C _{6) alkyl,} C 3 -C ₈ ^cycloalkyl, optionally substituted by ^{R 14} _{(C 3} -C ₈₎ cycloalkyl _,, C 2 -C ₆ ^alkenyl, optionally substituted by ^{R 14} _(C 2 ~C _{6) alkenyl,} C 3 -C ₈ ^{cycloalkenyl,} optionally substituted by ^{R 14} (C ₃ -C _{8) cycloalkenyl,} optionally substituted by C 2 -C _{6 ^{alkynyl, R 14 (C 2 ~C 6}} ) alkynyl, phenyl, phenyl substituted by _{(Z) q,} naphthyl, _{(Z) q} Naphthyl substituted by D1-32, D1-33, D1-34, D1-35, D1-36, D1-37, D1-38, D1-39, D1-79, D1-80, D1-81, D1-82, D1-84, D1-85, D1-87, D1-92, D1-93, D1-95, D1-96 or D1-98,
R ⁸ is a hydrogen _atom, C 1 -C ₆ ^alkyl, optionally substituted by ^{R 14} _(C 1 ~C _{6) alkyl,} C 3 -C ₈ ^cycloalkyl, optionally substituted by ^{R 14} _{(C 3} -C ₈₎ cycloalkyl _,, C 2 -C ₆ ^alkenyl, optionally substituted by ^{R 14} _(C 2 ~C _{6) alkenyl,} C 3 -C ₈ ^{cycloalkenyl,} optionally substituted by ^{R 14} (C ₃ -C ₈ ) cycloalkenyl, C ₂ -C ₆ alkynyl or (C ₂ -C ₆ ) alkynyl optionally substituted by R ¹⁴ ,
R ^8a is a hydrogen _atom, C 1 -C ₆ ^alkyl, optionally substituted by ^{R 14a} _(C 1 ~C ₆₎ alkyl, phenyl, phenyl substituted by _{(Z) q,} naphthyl, the _{(Z) q} Substituted naphthyl, D1-32, D1-33, D1-34, D1-35, D1-36, D1-37, D1-38, D1-39, D1-79, D1-80, D1-81, D1 -82, D1-84, D1-85, D1-87, D1-92, D1-93, D1-95, D1-96 or D1-98,
R ¹¹ represents C ₂ -C ₆ alkynyl or (C ₂ -C ₆ ) alkynyl optionally substituted by R ^14c ,
R ¹⁴ is halogen atom, ^{cyano, -OH, -OR 15, -SH,} -S (O) r R 15, phenyl, substituted phenyl, naphthyl, the _{(Z) q} is substituted by _{(Z) q} Naphthyl, D1-79, D1-80, D1-81, D1-82, D1-84, D1-85, D1-87, D1-92, D1-93, D1-95, D1-96 or D1-98 Represent,
R ^14a represents a halogen atom, cyano, —OH, —OR ^15a , —SH or —S (O) _r R ^15a ,
R ^14c represents a halogen atom, cyano, —OH, —OR ^15c , —SH or —S (O) _r R ^15c ,
R ¹⁵ _is, C 1 -C _{6 alkyl,} C 1 -C ₆ haloalkyl, phenyl, _(Z) phenyl substituted by _q, naphthyl, naphthyl substituted by _{(Z) q, D1-32, D1-33} , D1-34, D1-35, D1-36, D1-37, D1-38 or D1-39,
R ^15a and R ^15c each independently represent C ₁ -C ₆ alkyl;
D1-32, D1-33, D1-34, D1-35, D1-36, D1-37, D1-38, D1-39, D1-79, D1-80, D1-81, D1-82, D1- 84, D1-85, D1-87, D1-92, D1-93, D1-95, D1-96 and D1-98 each represent a ring represented by the following structural formula,

X ¹ and X ^1b are each independently 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 represent _alkylthio, C 1 -C _{6 haloalkylthio,} C 1 -C _{6 alkylsulfinyl,} C 1 -C _{6 haloalkylsulfinyl,} a C 1 -C ₆ alkylsulfonyl or _C 1 -C ₆ haloalkylsulfonyl, g1 or when g4 represents an integer of 2 or more, each X ¹ may be also or different from each other the same as each other, or, f5, f7 or When 9 represents an integer of 2 or more, each X ^1b may be or different from each other the same as each other, further, when two which X ^1b are substituted on the same carbon, the two X ^1b oxo together, thioxo, _imino, C 1 -C _{6 alkylimino,} may form a C 1 -C ₆ alkoxyimino or _C 1 -C ₆ alkylidene,
Z 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 to} C ₆ haloalkylthio, C _{1 to} C ₆ alkylsulfinyl, C _{1 to} C ₆ haloalkylsulfinyl, C _{1 to} C ₆ alkylsulfonyl or C _{1 to} C ₆ haloalkylsulfonyl, and q represents an integer of 2 or more Each Z may be the same as or different from each other;
R ^28a represents a halogen atom, —OH, —OR ²⁹ , —SH or —S (O) _r R ²⁹ ,
R ²⁹ represents C ₁ -C ₆ alkyl,
g1 and n each independently represent an integer of 0, 1, 2, or 3;
g4 represents an integer of 0, 1, 2, 3 or 4;
f5 represents an integer of 0, 1, 2, 3, 4 or 5,
f7 represents an integer of 0, 1, 2, 3, 4, 5, 6 or 7,
f9 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9,
q represents an integer of 1, 2, 3, 4 or 5;
m1, m2 and m3 each independently represent an integer of 0 or 1,
r and r2 each independently represents an integer of 0, 1 or 2. Or a salt thereof.

[2]
A ¹ represents -CR ¹
R ¹ and R ³ each independently represent a hydrogen atom, a halogen atom or C ₁ -C ₆ alkyl;
R ² is a thiazole 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,
R ³ represents a hydrogen atom, a halogen atom or C ₁ -C ₆ alkyl,
R ^a represents C ₂ -C ₆ alkynyl,
R ^b represents —C (O) OR ^6a , —C (O) R ⁷ or —C (O) N (R ⁸ ) R ^8a ,
R ^6a represents C ₁ -C ₆ alkyl;
R ⁷ _is, C 1 -C ₆ ^alkyl, optionally substituted by ^{R 14} _(C 1 ~C ₆₎ ^alkyl, optionally by optionally substituted by ^{R 14} _(C 2 ~C ₆₎ alkenyl or ^{R 14} Represents substituted (C ₃ -C ₈ ) cycloalkyl,
R ⁸ represents (C ₁ -C ₆ ) alkyl optionally substituted with R ¹⁴ ;
R ^8a represents a hydrogen atom or C ₁ -C ₆ alkyl;
R ¹⁴ represents a halogen atom or —S (O) _r R ¹⁵ ;
R ¹⁵ represents C ₁ -C ₆ alkyl,
m1 and n represent 0;
r is a thiazole derivative or a salt thereof according to the above [2], wherein r represents an integer of 0, 1 or 2.

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

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

[6]
A mammal or bird internal or ectoparasite control agent containing one or more selected from the thiazole derivatives and salts thereof described in [1] to [3] as active ingredients.

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

[8]
The soil treatment agent which contains 1 type, or 2 or more types chosen from the thiazole derivative and its salt as described in said [1]-[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.

  The compounds included in the present invention may have geometrical isomers of E-form and Z-form depending on the type of substituent, and the present invention is not limited to these E-form, Z-form or E-form. And a mixture containing the Z-form in an arbitrary ratio. 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, etc. 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.

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

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

In the present specification, C _a -C _b haloalkyl is represented by a linear or branched chain having _a to _b carbon atoms in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom. Represents a hydrocarbon group, and when substituted by two or more halogen atoms, the halogen atoms may be the same as or different from each other. For example, fluoromethyl group, chloromethyl group, bromomethyl group, iodomethyl group, difluoromethyl group, dichloromethyl group, trifluoromethyl group, chlorodifluoromethyl group, trichloromethyl group, bromodifluoromethyl group, 2-fluoroethyl group, 2- Chloroethyl group, 2-bromoethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, 2-chloro-2,2-difluoroethyl group, 2,2,2-trichloroethyl group, 1 , 1,2,2-tetrafluoroethyl group, 2-chloro-1,1,2-trifluoroethyl group, pentafluoroethyl group, 3,3,3-trifluoropropyl group, 2,2,3,3 , 3-pentafluoropropyl group, 1,1,2,3,3,3-hexafluoropropyl group, heptafluoropropyl group 2,2,2-trifluoro-1- (trifluoromethyl) ethyl group, 1,2,2,2-tetrafluoro-1- (trifluoromethyl) ethyl group, 2,2,3,3,4, Specific examples include 4,4-heptafluorobutyl group, nonafluorobutyl group and the like, and each is selected within the range of the number of carbon atoms designated.

In the present specification, C _a -C _b cycloalkyl represents a cyclic hydrocarbon group having a carbon number of _a to _b , and forms a monocyclic or complex ring structure having 3 to 6 members. I can do it. Each ring may be optionally substituted with an alkyl group within the range of the specified number of carbon atoms. Specific examples include, 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.

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

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

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

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.

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

Optionally substituted by ^{R 14} herein _(C a _{~C b)} optionally substituted by cycloalkyl or ^{R 28a} _(C ^a _{~C b)} notation cycloalkyl or the like, any of ^{R 14} or R ^A cycloalkyl group having the above meaning consisting of _a to _b carbon atoms in which hydrogen atoms bonded to carbon atoms are optionally substituted by (C _a -C _b ) cycloalkyl optionally substituted by ^28a Selected and selected for each specified number of carbon atoms. At this time, when two or more substituents R ¹⁴ or R ^28a on each (C _a -C _b ) cycloalkyl group are present, each R ¹⁴ or R ^28a may be the same as or different from each other, and further May be a ring structure moiety, a side chain moiety, or both.

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

Herein is optionally substituted by ^{R 14} _(C a ^~C _b) optionally substituted by cycloalkenyl or ^{R 28a} _(C ^{a ~C} _b) the representation of such cycloalkenyl, any ^{R 14} or R ^28a represents a cycloalkenyl group as defined above, wherein the number of carbon atoms optionally substituted with hydrogen atoms bonded to carbon atoms is ab, selected within the range of each specified number of carbon atoms . At this time, when two or more substituents R ¹⁴ or R ^28a on each (C _a -C _b ) cycloalkenyl group are present, each R ¹⁴ or R ^28a may be the same or different from each other, and further substituted The position may be a ring structure moiety, a side chain moiety, or both.

Optionally substituted by ^{R 5b} herein _(C a _{~C b)} ^alkynyl, optionally substituted by ^{R 14} _(C a _{~C b)} ^alkynyl, optionally substituted by ^{R 14c} _(C a ~ C _b ) Alkynyl or R ^28a optionally substituted (C _a -C _b ) Alkynyl and the like are represented by any R ^5b , R ¹⁴ , R ^14c or R ^28a , and a hydrogen atom bonded to a carbon atom is optional. Represents an alkynyl group having the above meaning consisting of a to b carbon atoms, and is selected in the range of each designated number of carbon atoms. At this time, when two or more substituents R ^5b , R ¹⁴ , R ^14c or R ^28a on each (C _a -C _b ) alkynyl group are present, each R ^5b , R ¹⁴ , R ^14c or R ^{28a is present.} May be the same as or different from each other.

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

  Manufacturing method A

Formula (4) [wherein A ¹ , R ² , R ³ , R ^6a and n represent the same meaning as described above. The compound represented by formula (5) [wherein R ^a represents the same meaning as described above, and J ^b represents a leaving group such as a halogen atom, —OH, —OSO ₂ CH ₃ , —OSO ₂ CF _3, etc.] Represents. In the formula (6), A ¹ , R ² , R ³ , R ^6a , R ^a and n have the same meaning as described above. This invention compound represented by this can be obtained.

  In this reaction, the compound represented by the formula (5) can be used in the range of 0.5 to 50 equivalents with respect to 1 equivalent of the compound represented by the formula (4). If necessary, bases such as hydrochloric acid, sulfuric acid, p-toluenesulfonic acid, etc., potassium carbonate, triethylamine, pyridine, 4- (dimethylamino) pyridine, sodium hydride, sodium hydroxide, potassium hydroxide, or diethylazo Mitsunobu reaction using dicarboxylate and triphenylphosphine or the like 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.

  Some of the compounds represented by formula (5) are known compounds, and some of them are commercially available. Others can be synthesized according to known methods described in the literature.

  Manufacturing method B

A compound represented by the formula (6) that can be synthesized according to the method described in the production method A is reacted with an acid or a base to obtain a compound represented by the formula (7) [wherein A ¹ , R ² , R ³ , R ^a And n represent the same meaning as described above. The compound represented by this can be obtained.

  As the acid, hydrochloric acid, sulfuric acid, p-toluenesulfonic acid, trifluoroacetic acid and the like can be used. As the base, potassium carbonate, sodium hydroxide or the like can be used.

  This reaction may be carried out without solvent, but a solvent may be used. For example, polar solvents such as acetonitrile and water, alcohols such as methanol, ethanol, propanol, 2-propanol and ethylene glycol, ethers such as diethyl ether, tetrahydrofuran and diphenyl ether, and 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.

The compound represented by the formula (7) thus obtained was converted to the formula (8-1) [wherein R ⁷ represents the same meaning as described above. And a compound represented by formula (9) [wherein A ¹ , R ² , R ³ , R ⁷ , R ^a and n have the same meaning as described above]. This invention compound represented by this can be synthesize | combined. In this reaction, the compound represented by the formula (8-1) can be used in the range of 0.5 to 50 equivalents with respect to 1 equivalent of the compound represented by the formula (7). If necessary, a base such as potassium carbonate, triethylamine, pyridine, 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, 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, methylene chloride , Halogenated hydrocarbons such as 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 formula (8-1) are known compounds, and some of them are commercially available. Others can be synthesized according to known methods described in the literature.

Moreover, the compound represented by Formula (7) is replaced with Formula (8-2) [wherein R ⁷ represents the same meaning as described above. The compound of the present invention represented by formula (9) can also be synthesized by reacting the compound represented by formula (9) with a condensing agent. In this reaction, 1 to 4 equivalents of WSC {1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride}, CDI (1,1) per 1 equivalent of the compound represented by formula (8-2) A condensing agent such as' -carbonyldiimidazole) can be used. Moreover, the compound represented by Formula (8-2) can be used in 0.5-50 equivalent with respect to 1 equivalent of compounds represented by Formula (7). If necessary, a base such as potassium carbonate, triethylamine, pyridine, 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, 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, methylene chloride , Halogenated hydrocarbons such as 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 formula (8-2) 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

A compound represented by formula (7), which can be synthesized according to the method described in Production Method B, and formula (10) [wherein R ⁸ represents the same meaning as described above; By reacting the compound represented by formula (12), A ¹ , R ² , R ³ , R ⁸ , R ^a and n represent the same meaning as described above. This invention compound represented by this can be obtained. In this reaction, the compound represented by the formula (10) can be used in the range of 0.5 to 50 equivalents with respect to 1 equivalent of the compound represented by the formula (7). If necessary, a base such as potassium carbonate, triethylamine, pyridine, 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, 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, methylene chloride , Halogenated hydrocarbons such as chloroform and carbon tetrachloride, and aliphatic hydrocarbons such as pentane and n-hexane.

  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 formula (10) are known compounds, and some of them are commercially available. Others can be synthesized according to known methods described in the literature.

In addition, the compound represented by the formula (7) and the formula (11) [wherein R ⁸ represents the same meaning as described above. The compound of the present invention represented by the formula (12) can also be synthesized by reacting the compound represented by the formula:

  In this reaction, 1 to 4 equivalents of CDI (1,1′-carbonyldiimidazole), bis (trichloromethyl) carbonate, and the like can be used with respect to 1 equivalent of the compound represented by formula (11). Moreover, the compound represented by Formula (11) can be used in 0.5-50 equivalent with respect to 1 equivalent of compounds represented by Formula (7). If necessary, a base such as potassium carbonate, triethylamine, pyridine, 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, 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, methylene chloride , Halogenated hydrocarbons such as 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 formula (11) are known compounds, and some of them are commercially available. Others can be synthesized according to known methods described in the literature.

  Manufacturing method D

A compound represented by formula (9), which can be synthesized according to the method described in Production Method B, diphosphorus pentasulfide, diphosphorus pentasulfide-HMDO (hexamethyldisiloxane), Lawson's reagent [Lawsson's Reagent; By reacting a sulfurizing agent such as 2,4-bis (4-methoxyphenyl) -1,3,4,4-dithiadiphosphetane-2,4-disulfide], a compound represented by the formula (35) [wherein A ¹ , R ² , R ³ , R ⁷ , R ^a and n represent the same meaning as described above. This invention compound represented by this can be obtained.

  The sulfurizing agent used in this reaction can be used in the range of 0.5 to 50 equivalents relative to 1 equivalent of the compound represented by formula (9).

  If necessary, a base such as potassium carbonate, 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.

  Manufacturing method E

Formula (41) [wherein A ¹ , R ² , R ³ , R ⁷ and n represent the same meaning as described above. The compound of the present invention represented by formula (9) is reacted with the compound represented by formula (5) using the same method as described in Production Method A. It can also be obtained.

  The reaction from production method A to production method E 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 E, 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.

  The compound represented by formula (4) used in production method A can be synthesized, for example, as follows.

  Reaction formula 1

Formula (2) [wherein A ¹ , R ² , R ³ and n represent the same meaning as described above. ] A compound represented by diphenylphosphoryl azide (DPPA) and formula (3) [wherein R ^6b represents C ₁ -C ₆ alkyl. In the formula (4), A ¹ , R ² , R ³ , R ^6a and n represent the same meaning as described above. The compound represented by this can be obtained.

  In this reaction, DPPA can be used in the range of 0.5 to 50 equivalents relative to 1 equivalent of the compound represented by formula (2), and the compound represented by formula (3) is represented by formula (2). Can be used in the range of 1 equivalent to the amount of solvent relative to 1 equivalent of the compound represented by formula (1). If necessary, a base such as potassium carbonate, 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.

  Some of the compounds represented by formula (2) are known compounds, and some of them are commercially available. Others can be synthesized according to known methods described in the literature.

  Some of the compounds represented by formula (3) are known compounds, and some of them are commercially available. Others can be synthesized according to known methods described in the literature.

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

  Reaction formula 2

Formula (4) [wherein A ¹ , R ² , R ³ , R ^6a and n represent the same meaning as described above. The compound represented by the formula (13) [wherein A ¹ , R ² , R ³ , and n are as defined above] is reacted with an acid or a base using the same method as in Production Method B. Represents. The compound represented by this can be obtained.

Formula (13) [wherein A ¹ , R ² , R ³ and n represent the same meaning as described above. The compound represented by formula (8-1) or the compound represented by formula (8-2) is reacted with the compound represented by formula (8-1) using the same method as in Production Method B. 41) [wherein A ¹ , R ² , R ³ , R ⁷ and n represent the same meaning as described above. This invention compound represented by this can be obtained.

  Specific examples of the active compound included in the present invention include compounds shown in Table 1. However, the compounds in Table 1 are for illustrative purposes, and the present invention is not limited thereto. In the table, the substituent described as Me represents a methyl group, hereinafter, Et represents an ethyl group, n-Pr and Pr-n represent normal propyl groups, i-Pr and Pr-i. Is an isopropyl group, c-Pr and Pr-c are cyclopropyl groups, n-Bu and Bu-n normal butyl groups, s-Bu and Bu-s are secondary butyl groups, i-Bu and Bu-i. Is an isobutyl group, t-Bu and Bu-t are tertiary butyl groups, c-Bu and Bu-c are cyclobutyl groups, n-Pen and Pen-n are normal pentyl groups, c-Pen and Pen- c is a cyclopentyl group, n-Hex and Hex-n are normal hexyl groups, c-Hex and Hex-c are cyclohexyl groups, Hept is a heptyl group, Oct is an octyl group, and Ph is a fethyl group. It represents Le group, respectively.

In the table, D1-32a, D1-32b, D1-33a, D1-33b, D1-34a, D1-34b, D1-35a, D1-35b, D1-36a, D1-36b, D1-37a, D1-37b D1-38a, D1-38b, D1-39a, D1-39b, D1-79a, D1-80a, D1-81a, D1-81b, D1-82a, D1-82b, D1-84a, D1-85a, D1 -87a, D1-92a, D1-92b, D1-92c, D1-93a, D1-93b, D1-93c, D1-95a, D1-96a, D1-98a, D1-103b, D1-103c, D1-103d , D1-103e, D1-103f, D1-103g, D1-103h, D1-103i, D1-108a, and D1-108b have the following structures. The stands, stands D1-32b, D1-33b, D1-34b, D1-36b, D1-37b, the D1-38b and structure number marked on the type D1-39b the substitution position of ^{X 1,} D1- The number written in the structural formula 108b represents the substitution position of Z.

[Table 1]

―――――――――――――――――――――――
R^a                        R^b-1
―――――――――――――――――――――――
CH₂C≡CH OMe
CH₂C≡CH OEt
CH₂C≡CH OPr-n
CH₂C≡CH OPr-i
CH₂C≡CH OPr-c
CH₂C≡CH OBu-n
CH₂C≡CH OBu-i
CH₂C≡CH OBu-c
CH₂C≡CH OBu-s
CH₂C≡CH OBu-t
CH₂C≡CH OPen-n
CH₂C≡CH OPen-c
CH₂C≡CH OHex-n
CH₂C≡CH OHex-c
CH₂C≡CH Me
CH₂C≡CH Et
CH₂C≡CH Pr-n
CH₂C≡CH Pr-i
CH₂C≡CH Pr-c
CH₂C≡CH Bu-n
CH₂C≡CH Bu-i
CH₂C≡CH Bu-c
CH₂C≡CH Bu-s
CH₂C≡CH Bu-t
CH₂C≡CH Pen-n
CH₂C≡CH Pen-c
CH₂C≡CH Hex-n
CH₂C≡CH Hex-c
CH₂C≡CH CH₂SMe
CH₂C≡CH CH₂S (O) Me
CH₂C≡CH CH₂S (O)₂Me
CH₂C≡CH CH (Me) SMe
CH₂C≡CH CH (Me) S (O) Me
CH₂C≡CH CH (Me) S (O)₂Me
CH₂C≡CH C (Me)₂SMe
CH₂C≡CH C (Me)₂S (O) Me
CH₂C≡CH C (Me)₂S (O)₂Me
CH₂C≡CH CH₂SEt
CH₂C≡CH CH₂S (O) Et
CH₂C≡CH CH₂S (O)₂Et
CH₂C≡CH CH (Me) SEt
CH₂C≡CH CH (Me) S (O) Et
CH₂C≡CH CH (Me) S (O)₂Et
CH₂C≡CH C (Me)₂SEt
CH₂C≡CH C (Me)₂S (O) Et
CH₂C≡CH C (Me)₂S (O)₂Et
CH₂C≡CH CH₂CH₂SMe
CH₂C≡CH CH₂CH₂S (O) Me
CH₂C≡CH CH₂CH₂S (O)₂Me
CH₂C≡CH CH (Me) CH₂SMe
CH₂C≡CH CH (Me) CH₂S (O) Me
CH₂C≡CH CH (Me) CH₂S (O)₂Me
CH₂C≡CH C (Me)₂CH₂SMe
CH₂C≡CH C (Me)₂CH₂S (O) Me
CH₂C≡CH C (Me)₂CH₂S (O)₂Me
CH₂C≡CH CH₂CH (Me) SMe
CH₂C≡CH CH₂CH (Me) S (O) Me
CH₂C≡CH CH₂CH (Me) S (O)₂Me
CH₂C≡CH CH₂C (Me)₂SMe
CH₂C≡CH CH₂C (Me)₂S (O) Me
CH₂C≡CH CH₂C (Me)₂S (O)₂Me
CH₂C≡CH CH (Me) CH (Me) SMe
CH₂C≡CH CH (Me) CH (Me) S (O) Me
CH₂C≡CH CH (Me) CH (Me) S (O)₂Me
CH₂C≡CH C (Me)₂CH (Me) SMe
CH₂C≡CH C (Me)₂CH (Me) S (O) Me
CH₂C≡CH C (Me)₂CH (Me) S (O)₂Me
CH₂C≡CH CH (Me) C (Me)₂SMe
CH₂C≡CH CH (Me) C (Me)₂S (O) Me
CH₂C≡CH CH (Me) C (Me)₂S (O)₂Me
CH₂C≡CH C (Me)₂C (Me)₂SMe
CH₂C≡CH C (Me)₂C (Me)₂S (O) Me
CH₂C≡CH C (Me)₂C (Me)₂S (O)₂Me
CH₂C≡CH CH₂CF_Three
CH₂C≡CH CH (Me) CF_Three
CH₂C≡CH CH₂CF₂CF_Three
CH₂C≡CH CH (Me) CF₂CF_Three
CH₂C≡CH CH₂CH₂CF_Three
CH₂C≡CH CH (Me) CH₂CF_Three
CH₂C≡CH CH₂CH (Me) CF_Three
CH₂C≡CH CH₂CH (CF_Three)₂
CH₂C≡CH CH (Me) CH (CF_Three)₂
CH₂C≡CH CH₂CF (CF_Three)₂
CH₂C≡CH CH (Me) CF (CF_Three)₂
CH₂C≡CH CH (CF_ThreeSMe
CH₂C≡CH CH (CF_Three) S (O) Me
CH₂C≡CH CH (CF_Three) S (O)₂Me
CH₂C≡CH CH (CF_Three) SEt
CH₂C≡CH CH (CF_Three) S (O) Et
CH₂C≡CH CH (CF_Three) S (O)₂Et
CH₂C≡CH CH (CF_Three) CH₂SMe
CH₂C≡CH CH (CF_Three) CH₂S (O) Me
CH₂C≡CH CH (CF_Three) CH₂S (O)₂Me
CH₂C≡CH CH₂CH (CF_ThreeSMe
CH₂C≡CH CH₂CH (CF_Three) S (O) Me
CH₂C≡CH CH₂CH (CF_Three) S (O)₂Me
CH₂C≡CH D1-81a
CH₂C≡CH D1-82a
CH₂C≡CH D1-84a
CH₂C≡CH D1-85a
CH₂C≡CH D1-87a
CH₂C≡CH D1-92a
CH₂C≡CH D1-93a
CH₂C≡CH D1-95a
CH₂C≡CH D1-96a
CH₂C≡CH D1-98a
CH₂C≡CH D1-103b
CH₂C≡CH D1-103c
CH₂C≡CH D1-103d
CH₂C≡CH D1-103e
CH₂C≡CH D1-103f
CH₂C≡CH D1-103g
CH₂C≡CH D1-103h
CH₂C≡CH D1-103i
CH₂C≡CH CH₂(D1-81a)
CH₂C≡CH CH₂(D1-82a)
CH₂C≡CH CH₂(D1-84a)
CH₂C≡CH CH₂(D1-85a)
CH₂C≡CH CH₂(D1-87a)
CH₂C≡CH CH₂(D1-92a)
CH₂C≡CH CH₂(D1-93a)
CH₂C≡CH CH₂(D1-95a)
CH₂C≡CH CH₂(D1-96a)
CH₂C≡CH CH₂(D1-98a)
CH₂C≡CH CH₂(D1-103b)
CH₂C≡CH CH₂S (D1-32a)
CH₂C≡CH CH₂S {D1-32b (2-Me)}
CH₂C≡CH CH₂S {D1-32b (3-CF_Three)}
CH₂C≡CH CH₂S {D1-32b (4-Cl)}
CH₂C≡CH CH₂S {D1-32b (5-OMe)}
CH₂C≡CH CH₂S (D1-33a)
CH₂C≡CH CH₂S {D1-33b (2-SMe)}
CH₂C≡CH CH₂S {D1-33b (4-OCF_Three)}
CH₂C≡CH CH₂S {D1-33b (5-SCF_Three)}
CH₂C≡CH CH₂S {D1-33b (6-Pr-c)}
CH₂C≡CH CH₂S (D1-34a)
CH₂C≡CH CH₂S {D1-34b (2-CH₂CH = CH₂)}
CH₂C≡CH CH₂S {D1-34b (3-CH₂C≡CH)}
CH₂C≡CH CH₂S {D1-34b (5-F)}
CH₂C≡CH CH₂S {D1-34b (6-Br)}
CH₂C≡CH CH₂S (D1-35a)
CH₂C≡CH CH₂S (D1-35b
CH₂C≡CH CH₂S (D1-36a)
CH₂C≡CH CH₂S {D1-36b (2-Et)}
CH₂C≡CH CH₂S {D1-36b [4-S (O) Me]}
CH₂C≡CH CH₂S {D1-36b [5-S (O)₂Me]}
CH₂C≡CH CH₂S (D1-37a)
CH₂C≡CH CH₂S {D1-37b [4-S (O) Me]}
CH₂C≡CH CH₂S {D1-37b [5-S (O)₂Me]}
CH₂C≡CH CH₂S {D1-37b (6-Pr-i)}
CH₂C≡CH CH₂S (D1-38a)
CH₂C≡CH CH₂S {D1-38b [2-S (O) CF_Three]}
CH₂C≡CH CH₂S {D1-38b [4-S (O)₂CF_Three]}
CH₂C≡CH CH₂S {D1-38b (6-OH)}
CH₂C≡CH CH₂S (D1-39a)
CH₂C≡CH CH₂S {D1-39b (2-CN)}
CH₂C≡CH CH₂S {D1-39b (3-NO₂)}
CH₂C≡CH CH₂S {D1-39b [5-CH₂CH = C (Cl)₂]}
CH₂C≡CH CH₂S (D1-108a)
CH₂C≡CH CH₂S {D1-108b (2-CH₂CH = CH₂)}
CH₂C≡CH CH₂S {D1-108b (3-CH₂C≡CH)}
CH₂C≡CH CH₂S {D1-108b (4-CN)}
CH₂C≡CH CH₂S {D1-108b (2-NO₂)}
CH₂C≡CH CH₂S {D1-108b (2-F)}
CH₂C≡CH CH₂S {D1-108b (2-Cl)}
CH₂C≡CH CH₂S {D1-108b (2-Br)}
CH₂C≡CH CH₂S {D1-108b (2-I)}
CH₂C≡CH CH₂S {D1-108b (2-Me)}
CH₂C≡CH CH₂S {D1-108b (4-OMe)}
CH₂C≡CH CH₂S {D1-108b (4-SMe)}
CH₂C≡CH CH₂S {D1-108b [4-S (O) Me]}
CH₂C≡CH CH₂S {D1-108b [4-S (O)₂Me]}
CH₂C≡CH CH₂S {D1-108b (4-SMe)}
CH₂C≡CH CH₂S {D1-108b (3-CF_Three)}
CH₂C≡CH CH₂S {D1-108b (4-OCF_Three)}
CH₂C≡CH CH₂S {D1-108b (2-SCF_Three)}
CH₂C≡CH CH₂S {D1-108b [2-S (O) CF_Three]}
CH₂C≡CH CH₂S {D1-108b [2-S (O)₂CF_Three]}
CH₂C≡CH CH₂S {D1-108b (2-OH)}
CH₂C≡CH CH₂S {D1-108b (2-SH)}
CH₂C≡CH NHMe
CH₂C≡CH NHEt
CH₂C≡CH NHPr-n
CH₂C≡CH NHPr-i
CH₂C≡CH NHPr-c
CH₂C≡CH NHBu-n
CH₂C≡CH NHBu-i
CH₂C≡CH NHBu-c
CH₂C≡CH NHBu-s
CH₂C≡CH NHBu-t
CH₂C≡CH NHPen-n
CH₂C≡CH NHPen-c
CH₂C≡CH NHHex-n
CH₂C≡CH NHHex-c
CH₂C≡CH NHCH₂CF_Three
CH₂C≡CH NMe₂
CH₂C≡CH N (Me) Et
CH₂C≡CH N (Me) Pr-n
CH₂C≡CH N (Me) Pr-i
CH₂C≡CH N (Me) Pr-c
CH₂C≡CH N (Me) Bu-n
CH₂C≡CH N (Me) Bu-i
CH₂C≡CH N (Me) Bu-c
CH₂C≡CH N (Me) Bu-s
CH₂C≡CH N (Me) Bu-t
CH₂C≡CH N (Me) Pen-n
CH₂C≡CH N (Me) Pen-c
CH₂C≡CH N (Me) Hex-n
CH₂C≡CH N (Me) Hex-c
CH₂C≡CH N (Me) CH₂CF_Three
CH (Me) C≡CH OMe
CH (Me) C≡CH OEt
CH (Me) C≡CH OPr-n
CH (Me) C≡CH OPr-i
CH (Me) C≡CH OPr-c
CH (Me) C≡CH OBu-n
CH (Me) C≡CH OBu-i
CH (Me) C≡CH OBu-c
CH (Me) C≡CH OBu-s
CH (Me) C≡CH OBu-t
CH (Me) C≡CH OPen-n
CH (Me) C≡CH OPen-c
CH (Me) C≡CH OHex-n
CH (Me) C≡CH OHex-c
CH (Me) C≡CH Me
CH (Me) C≡CH Et
CH (Me) C≡CH Pr-n
CH (Me) C≡CH Pr-i
CH (Me) C≡CH Pr-c
CH (Me) C≡CH Bu-n
CH (Me) C≡CH Bu-i
CH (Me) C≡CH Bu-c
CH (Me) C≡CH Bu-s
CH (Me) C≡CH Bu-t
CH (Me) C≡CH Pen-n
CH (Me) C≡CH Pen-c
CH (Me) C≡CH Hex-n
CH (Me) C≡CH Hex-c
CH (Me) C≡CH CH₂SMe
CH (Me) C≡CH CH₂S (O) Me
CH (Me) C≡CH CH₂S (O)₂Me
CH (Me) C≡CH CH (Me) SMe
CH (Me) C≡CH CH (Me) S (O) Me
CH (Me) C≡CH CH (Me) S (O)₂Me
CH (Me) C≡CH C (Me)₂SMe
CH (Me) C≡CH C (Me)₂S (O) Me
CH (Me) C≡CH C (Me)₂S (O)₂Me
CH (Me) C≡CH CH₂SEt
CH (Me) C≡CH CH₂S (O) Et
CH (Me) C≡CH CH₂S (O)₂Et
CH (Me) C≡CH CH (Me) SEt
CH (Me) C≡CH CH (Me) S (O) Et
CH (Me) C≡CH CH (Me) S (O)₂Et
CH (Me) C≡CH C (Me)₂SEt
CH (Me) C≡CH C (Me)₂S (O) Et
CH (Me) C≡CH C (Me)₂S (O)₂Et
CH (Me) C≡CH CH₂CH₂SMe
CH (Me) C≡CH CH₂CH₂S (O) Me
CH (Me) C≡CH CH₂CH₂S (O)₂Me
CH (Me) C≡CH CH (Me) CH₂SMe
CH (Me) C≡CH CH (Me) CH₂S (O) Me
CH (Me) C≡CH CH (Me) CH₂S (O)₂Me
CH (Me) C≡CH C (Me)₂CH₂SMe
CH (Me) C≡CH C (Me)₂CH₂S (O) Me
CH (Me) C≡CH C (Me)₂CH₂S (O)₂Me
CH (Me) C≡CH CH₂CH (Me) SMe
CH (Me) C≡CH CH₂CH (Me) S (O) Me
CH (Me) C≡CH CH₂CH (Me) S (O)₂Me
CH (Me) C≡CH CH₂C (Me)₂SMe
CH (Me) C≡CH CH₂C (Me)₂S (O) Me
CH (Me) C≡CH CH₂C (Me)₂S (O)₂Me
CH (Me) C≡CH CH (Me) CH (Me) SMe
CH (Me) C≡CH CH (Me) CH (Me) S (O) Me
CH (Me) C≡CH CH (Me) CH (Me) S (O)₂Me
CH (Me) C≡CH C (Me)₂CH (Me) SMe
CH (Me) C≡CH C (Me)₂CH (Me) S (O) Me
CH (Me) C≡CH C (Me)₂CH (Me) S (O)₂Me
CH (Me) C≡CH CH (Me) C (Me)₂SMe
CH (Me) C≡CH CH (Me) C (Me)₂S (O) Me
CH (Me) C≡CH CH (Me) C (Me)₂S (O)₂Me
CH (Me) C≡CH C (Me)₂C (Me)₂SMe
CH (Me) C≡CH C (Me)₂C (Me)₂S (O) Me
CH (Me) C≡CH C (Me)₂C (Me)₂S (O)₂Me
CH (Me) C≡CH CH₂CF_Three
CH (Me) C≡CH CH (Me) CF_Three
CH (Me) C≡CH CH₂CF₂CF_Three
CH (Me) C≡CH CH (Me) CF₂CF_Three
CH (Me) C≡CH CH₂CH₂CF_Three
CH (Me) C≡CH CH (Me) CH₂CF_Three
CH (Me) C≡CH CH₂CH (Me) CF_Three
CH (Me) C≡CH CH₂CH (CF_Three)₂
CH (Me) C≡CH CH (Me) CH (CF_Three)₂
CH (Me) C≡CH CH₂CF (CF_Three)₂
CH (Me) C≡CH CH (Me) CF (CF_Three)₂
CH (Me) C≡CH CH (CF_ThreeSMe
CH (Me) C≡CH CH (CF_Three) S (O) Me
CH (Me) C≡CH CH (CF_Three) S (O)₂Me
CH (Me) C≡CH CH (CF_Three) SEt
CH (Me) C≡CH CH (CF_Three) S (O) Et
CH (Me) C≡CH CH (CF_Three) S (O)₂Et
CH (Me) C≡CH CH (CF_Three) CH₂SMe
CH (Me) C≡CH CH (CF_Three) CH₂S (O) Me
CH (Me) C≡CH CH (CF_Three) CH₂S (O)₂Me
CH (Me) C≡CH CH₂CH (CF_ThreeSMe
CH (Me) C≡CH CH₂CH (CF_Three) S (O) Me
CH (Me) C≡CH CH₂CH (CF_Three) S (O)₂Me
CH (Me) C≡CH D1-81a
CH (Me) C≡CH D1-82a
CH (Me) C≡CH D1-84a
CH (Me) C≡CH D1-85a
CH (Me) C≡CH D1-87a
CH (Me) C≡CH D1-92a
CH (Me) C≡CH D1-93a
CH (Me) C≡CH D1-95a
CH (Me) C≡CH D1-96a
CH (Me) C≡CH D1-98a
CH (Me) C≡CH D1-103b
CH (Me) C≡CH D1-103c
CH (Me) C≡CH D1-103d
CH (Me) C≡CH D1-103e
CH (Me) C≡CH D1-103f
CH (Me) C≡CH D1-103g
CH (Me) C≡CH D1-103h
CH (Me) C≡CH D1-103i
CH (Me) C≡CH CH₂(D1-81a)
CH (Me) C≡CH CH₂(D1-82a)
CH (Me) C≡CH CH₂(D1-84a)
CH (Me) C≡CH CH₂(D1-85a)
CH (Me) C≡CH CH₂(D1-87a)
CH (Me) C≡CH CH₂(D1-92a)
CH (Me) C≡CH CH₂(D1-93a)
CH (Me) C≡CH CH₂(D1-95a)
CH (Me) C≡CH CH₂(D1-96a)
CH (Me) C≡CH CH₂(D1-98a)
CH (Me) C≡CH CH₂(D1-103b)
CH (Me) C≡CH CH₂S (D1-32a)
CH (Me) C≡CH CH₂S {D1-32b (2-Me)}
CH (Me) C≡CH CH₂S {D1-32b (3-CF_Three)}
CH (Me) C≡CH CH₂S {D1-32b (4-Cl)}
CH (Me) C≡CH CH₂S {D1-32b (5-OMe)}
CH (Me) C≡CH CH₂S (D1-33a)
CH (Me) C≡CH CH₂S {D1-33b (2-SMe)}
CH (Me) C≡CH CH₂S {D1-33b (4-OCF_Three)}
CH (Me) C≡CH CH₂S {D1-33b (5-SCF_Three)}
CH (Me) C≡CH CH₂S {D1-33b (6-Pr-c)}
CH (Me) C≡CH CH₂S (D1-34a)
CH (Me) C≡CH CH₂S {D1-34b (2-CH₂CH = CH₂)}
CH (Me) C≡CH CH₂S {D1-34b (3-CH₂C≡CH)}
CH (Me) C≡CH CH₂S {D1-34b (5-F)}
CH (Me) C≡CH CH₂S {D1-34b (6-Br)}
CH (Me) C≡CH CH₂S (D1-35a)
CH (Me) C≡CH CH₂S (D1-35b
CH (Me) C≡CH CH₂S (D1-36a)
CH (Me) C≡CH CH₂S {D1-36b (2-Et)}
CH (Me) C≡CH CH₂S {D1-36b [4-S (O) Me]}
CH (Me) C≡CH CH₂S {D1-36b [5-S (O)₂Me]}
CH (Me) C≡CH CH₂S (D1-37a)
CH (Me) C≡CH CH₂S {D1-37b [4-S (O) Me]}
CH (Me) C≡CH CH₂S {D1-37b [5-S (O)₂Me]}
CH (Me) C≡CH CH₂S {D1-37b (6-Pr-i)}
CH (Me) C≡CH CH₂S (D1-38a)
CH (Me) C≡CH CH₂S {D1-38b [2-S (O) CF_Three]}
CH (Me) C≡CH CH₂S {D1-38b [4-S (O)₂CF_Three]}
CH (Me) C≡CH CH₂S {D1-38b (6-OH)}
CH (Me) C≡CH CH₂S (D1-39a)
CH (Me) C≡CH CH₂S {D1-39b (2-CN)}
CH (Me) C≡CH CH₂S {D1-39b (3-NO₂)}
CH (Me) C≡CH CH₂S {D1-39b [5-CH₂CH = C (Cl)₂]}
CH (Me) C≡CH CH₂S (D1-108a)
CH (Me) C≡CH CH₂S {D1-108b (2-CH₂CH = CH₂)}
CH (Me) C≡CH CH₂S {D1-108b (3-CH₂C≡CH)}
CH (Me) C≡CH CH₂S {D1-108b (4-CN)}
CH (Me) C≡CH CH₂S {D1-108b (2-NO₂)}
CH (Me) C≡CH CH₂S {D1-108b (2-F)}
CH (Me) C≡CH CH₂S {D1-108b (2-Cl)}
CH (Me) C≡CH CH₂S {D1-108b (2-Br)}
CH (Me) C≡CH CH₂S {D1-108b (2-I)}
CH (Me) C≡CH CH₂S {D1-108b (2-Me)}
CH (Me) C≡CH CH₂S {D1-108b (4-OMe)}
CH (Me) C≡CH CH₂S {D1-108b (4-SMe)}
CH (Me) C≡CH CH₂S {D1-108b [4-S (O) Me]}
CH (Me) C≡CH CH₂S {D1-108b [4-S (O)₂Me]}
CH (Me) C≡CH CH₂S {D1-108b (4-SMe)}
CH (Me) C≡CH CH₂S {D1-108b (3-CF_Three)}
CH (Me) C≡CH CH₂S {D1-108b (4-OCF_Three)}
CH (Me) C≡CH CH₂S {D1-108b (2-SCF_Three)}
CH (Me) C≡CH CH₂S {D1-108b [2-S (O) CF_Three]}
CH (Me) C≡CH CH₂S {D1-108b [2-S (O)₂CF_Three]}
CH (Me) C≡CH CH₂S {D1-108b (2-OH)}
CH (Me) C≡CH CH₂S {D1-108b (2-SH)}
CH (Me) C≡CH NHMe
CH (Me) C≡CH NHEt
CH (Me) C≡CH NHPr-n
CH (Me) C≡CH NHPr-i
CH (Me) C≡CH NHPr-c
CH (Me) C≡CH NHBu-n
CH (Me) C≡CH NHBu-i
CH (Me) C≡CH NHBu-c
CH (Me) C≡CH NHBu-s
CH (Me) C≡CH NHBu-t
CH (Me) C≡CH NHPen-n
CH (Me) C≡CH NHPen-c
CH (Me) C≡CH NHHex-n
CH (Me) C≡CH NHHex-c
CH (Me) C≡CH NHCH₂CF_Three
CH (Me) C≡CH NMe₂
CH (Me) C≡CH N (Me) Et
CH (Me) C≡CH N (Me) Pr-n
CH (Me) C≡CH N (Me) Pr-i
CH (Me) C≡CH N (Me) Pr-c
CH (Me) C≡CH N (Me) Bu-n
CH (Me) C≡CH N (Me) Bu-i
CH (Me) C≡CH N (Me) Bu-c
CH (Me) C≡CH N (Me) Bu-s
CH (Me) C≡CH N (Me) Bu-t
CH (Me) C≡CH N (Me) Pen-n
CH (Me) C≡CH N (Me) Pen-c
CH (Me) C≡CH N (Me) Hex-n
CH (Me) C≡CH N (Me) Hex-c
CH (Me) C≡CH N (Me) CH₂CF_Three
C (Me)₂C≡CH OMe
C (Me)₂C≡CH OEt
C (Me)₂C≡CH OPr-n
C (Me)₂C≡CH OPr-i
C (Me)₂C≡CH OPr-c
C (Me)₂C≡CH OBu-n
C (Me)₂C≡CH OBu-i
C (Me)₂C≡CH OBu-c
C (Me)₂C≡CH OBu-s
C (Me)₂C≡CH OBu-t
C (Me)₂C≡CH OPen-n
C (Me)₂C≡CH OPen-c
C (Me)₂C≡CH OHex-n
C (Me)₂C≡CH OHex-c
C (Me)₂C≡CH Me
C (Me)₂C≡CH Et
C (Me)₂C≡CH Pr-n
C (Me)₂C≡CH Pr-i
C (Me)₂C≡CH Pr-c
C (Me)₂C≡CH Bu-n
C (Me)₂C≡CH Bu-i
C (Me)₂C≡CH Bu-c
C (Me)₂C≡CH Bu-s
C (Me)₂C≡CH Bu-t
C (Me)₂C≡CH Pen-n
C (Me)₂C≡CH Pen-c
C (Me)₂C≡CH Hex-n
C (Me)₂C≡CH Hex-c
C (Me)₂C≡CH CH₂SMe
C (Me)₂C≡CH CH₂S (O) Me
C (Me)₂C≡CH CH₂S (O)₂Me
C (Me)₂C≡CH CH (Me) SMe
C (Me)₂C≡CH CH (Me) S (O) Me
C (Me)₂C≡CH CH (Me) S (O)₂Me
C (Me)₂C≡CH C (Me)₂SMe
C (Me)₂C≡CH C (Me)₂S (O) Me
C (Me)₂C≡CH C (Me)₂S (O)₂Me
C (Me)₂C≡CH CH₂SEt
C (Me)₂C≡CH CH₂S (O) Et
C (Me)₂C≡CH CH₂S (O)₂Et
C (Me)₂C≡CH CH (Me) SEt
C (Me)₂C≡CH CH (Me) S (O) Et
C (Me)₂C≡CH CH (Me) S (O)₂Et
C (Me)₂C≡CH C (Me)₂SEt
C (Me)₂C≡CH C (Me)₂S (O) Et
C (Me)₂C≡CH C (Me)₂S (O)₂Et
C (Me)₂C≡CH CH₂CH₂SMe
C (Me)₂C≡CH CH₂CH₂S (O) Me
C (Me)₂C≡CH CH₂CH₂S (O)₂Me
C (Me)₂C≡CH CH (Me) CH₂SMe
C (Me)₂C≡CH CH (Me) CH₂S (O) Me
C (Me)₂C≡CH CH (Me) CH₂S (O)₂Me
C (Me)₂C≡CH C (Me)₂CH₂SMe
C (Me)₂C≡CH C (Me)₂CH₂S (O) Me
C (Me)₂C≡CH C (Me)₂CH₂S (O)₂Me
C (Me)₂C≡CH CH₂CH (Me) SMe
C (Me)₂C≡CH CH₂CH (Me) S (O) Me
C (Me)₂C≡CH CH₂CH (Me) S (O)₂Me
C (Me)₂C≡CH CH₂C (Me)₂SMe
C (Me)₂C≡CH CH₂C (Me)₂S (O) Me
C (Me)₂C≡CH CH₂C (Me)₂S (O)₂Me
C (Me)₂C≡CH CH (Me) CH (Me) SMe
C (Me)₂C≡CH CH (Me) CH (Me) S (O) Me
C (Me)₂C≡CH CH (Me) CH (Me) S (O)₂Me
C (Me)₂C≡CH C (Me)₂CH (Me) SMe
C (Me)₂C≡CH C (Me)₂CH (Me) S (O) Me
C (Me)₂C≡CH C (Me)₂CH (Me) S (O)₂Me
C (Me)₂C≡CH CH (Me) C (Me)₂SMe
C (Me)₂C≡CH CH (Me) C (Me)₂S (O) Me
C (Me)₂C≡CH CH (Me) C (Me)₂S (O)₂Me
C (Me)₂C≡CH C (Me)₂C (Me)₂SMe
C (Me)₂C≡CH C (Me)₂C (Me)₂S (O) Me
C (Me)₂C≡CH C (Me)₂C (Me)₂S (O)₂Me
C (Me)₂C≡CH CH₂CF_Three
C (Me)₂C≡CH CH (Me) CF_Three
C (Me)₂C≡CH CH₂CF₂CF_Three
C (Me)₂C≡CH CH (Me) CF₂CF_Three
C (Me)₂C≡CH CH₂CH₂CF_Three
C (Me)₂C≡CH CH (Me) CH₂CF_Three
C (Me)₂C≡CH CH₂CH (Me) CF_Three
C (Me)₂C≡CH CH₂CH (CF_Three)₂
C (Me)₂C≡CH CH (Me) CH (CF_Three)₂
C (Me)₂C≡CH CH₂CF (CF_Three)₂
C (Me)₂C≡CH CH (Me) CF (CF_Three)₂
C (Me)₂C≡CH CH (CF_ThreeSMe
C (Me)₂C≡CH CH (CF_Three) S (O) Me
C (Me)₂C≡CH CH (CF_Three) S (O)₂Me
C (Me)₂C≡CH CH (CF_Three) SEt
C (Me)₂C≡CH CH (CF_Three) S (O) Et
C (Me)₂C≡CH CH (CF_Three) S (O)₂Et
C (Me)₂C≡CH CH (CF_Three) CH₂SMe
C (Me)₂C≡CH CH (CF_Three) CH₂S (O) Me
C (Me)₂C≡CH CH (CF_Three) CH₂S (O)₂Me
C (Me)₂C≡CH CH₂CH (CF_ThreeSMe
C (Me)₂C≡CH CH₂CH (CF_Three) S (O) Me
C (Me)₂C≡CH CH₂CH (CF_Three) S (O)₂Me
C (Me)₂C≡CH D1-81a
C (Me)₂C≡CH D1-82a
C (Me)₂C≡CH D1-84a
C (Me)₂C≡CH D1-85a
C (Me)₂C≡CH D1-87a
C (Me)₂C≡CH D1-92a
C (Me)₂C≡CH D1-93a
C (Me)₂C≡CH D1-95a
C (Me)₂C≡CH D1-96a
C (Me)₂C≡CH D1-98a
C (Me)₂C≡CH D1-103b
C (Me)₂C≡CH D1-103c
C (Me)₂C≡CH D1-103d
C (Me)₂C≡CH D1-103e
C (Me)₂C≡CH D1-103f
C (Me)₂C≡CH D1-103g
C (Me)₂C≡CH D1-103h
C (Me)₂C≡CH D1-103i
C (Me)₂C≡CH CH₂(D1-81a)
C (Me)₂C≡CH CH₂(D1-82a)
C (Me)₂C≡CH CH₂(D1-84a)
C (Me)₂C≡CH CH₂(D1-85a)
C (Me)₂C≡CH CH₂(D1-87a)
C (Me)₂C≡CH CH₂(D1-92a)
C (Me)₂C≡CH CH₂(D1-93a)
C (Me)₂C≡CH CH₂(D1-95a)
C (Me)₂C≡CH CH₂(D1-96a)
C (Me)₂C≡CH CH₂(D1-98a)
C (Me)₂C≡CH CH₂(D1-103b)
C (Me)₂C≡CH CH₂S (D1-32a)
C (Me)₂C≡CH CH₂S {D1-32b (2-Me)}
C (Me)₂C≡CH CH₂S {D1-32b (3-CF_Three)}
C (Me)₂C≡CH CH₂S {D1-32b (4-Cl)}
C (Me)₂C≡CH CH₂S {D1-32b (5-OMe)}
C (Me)₂C≡CH CH₂S (D1-33a)
C (Me)₂C≡CH CH₂S {D1-33b (2-SMe)}
C (Me)₂C≡CH CH₂S {D1-33b (4-OCF_Three)}
C (Me)₂C≡CH CH₂S {D1-33b (5-SCF_Three)}
C (Me)₂C≡CH CH₂S {D1-33b (6-Pr-c)}
C (Me)₂C≡CH CH₂S (D1-34a)
C (Me)₂C≡CH CH₂S {D1-34b (2-CH₂CH = CH₂)}
C (Me)₂C≡CH CH₂S {D1-34b (3-CH₂C≡CH)}
C (Me)₂C≡CH CH₂S {D1-34b (5-F)}
C (Me)₂C≡CH CH₂S {D1-34b (6-Br)}
C (Me)₂C≡CH CH₂S (D1-35a)
C (Me)₂C≡CH CH₂S (D1-35b
C (Me)₂C≡CH CH₂S (D1-36a)
C (Me)₂C≡CH CH₂S {D1-36b (2-Et)}
C (Me)₂C≡CH CH₂S {D1-36b [4-S (O) Me]}
C (Me)₂C≡CH CH₂S {D1-36b [5-S (O)₂Me]}
C (Me)₂C≡CH CH₂S (D1-37a)
C (Me)₂C≡CH CH₂S {D1-37b [4-S (O) Me]}
C (Me)₂C≡CH CH₂S {D1-37b [5-S (O)₂Me]}
C (Me)₂C≡CH CH₂S {D1-37b (6-Pr-i)}
C (Me)₂C≡CH CH₂S (D1-38a)
C (Me)₂C≡CH CH₂S {D1-38b [2-S (O) CF_Three]}
C (Me)₂C≡CH CH₂S {D1-38b [4-S (O)₂CF_Three]}
C (Me)₂C≡CH CH₂S {D1-38b (6-OH)}
C (Me)₂C≡CH CH₂S (D1-39a)
C (Me)₂C≡CH CH₂S {D1-39b (2-CN)}
C (Me)₂C≡CH CH₂S {D1-39b (3-NO₂)}
C (Me)₂C≡CH CH₂S {D1-39b [5-CH₂CH = C (Cl)₂]}
C (Me)₂C≡CH CH₂S (D1-108a)
C (Me)₂C≡CH CH₂S {D1-108b (2-CH₂CH = CH₂)}
C (Me)₂C≡CH CH₂S {D1-108b (3-CH₂C≡CH)}
C (Me)₂C≡CH CH₂S {D1-108b (4-CN)}
C (Me)₂C≡CH CH₂S {D1-108b (2-NO₂)}
C (Me)₂C≡CH CH₂S {D1-108b (2-F)}
C (Me)₂C≡CH CH₂S {D1-108b (2-Cl)}
C (Me)₂C≡CH CH₂S {D1-108b (2-Br)}
C (Me)₂C≡CH CH₂S {D1-108b (2-I)}
C (Me)₂C≡CH CH₂S {D1-108b (2-Me)}
C (Me)₂C≡CH CH₂S {D1-108b (4-OMe)}
C (Me)₂C≡CH CH₂S {D1-108b (4-SMe)}
C (Me)₂C≡CH CH₂S {D1-108b [4-S (O) Me]}
C (Me)₂C≡CH CH₂S {D1-108b [4-S (O)₂Me]}
C (Me)₂C≡CH CH₂S {D1-108b (4-SMe)}
C (Me)₂C≡CH CH₂S {D1-108b (3-CF_Three)}
C (Me)₂C≡CH CH₂S {D1-108b (4-OCF_Three)}
C (Me)₂C≡CH CH₂S {D1-108b (2-SCF_Three)}
C (Me)₂C≡CH CH₂S {D1-108b [2-S (O) CF_Three]}
C (Me)₂C≡CH CH₂S {D1-108b [2-S (O)₂CF_Three]}
C (Me)₂C≡CH CH₂S {D1-108b (2-OH)}
C (Me)₂C≡CH CH₂S {D1-108b (2-SH)}
C (Me)₂C≡CH NHMe
C (Me)₂C≡CH NHEt
C (Me)₂C≡CH NHPr-n
C (Me)₂C≡CH NHPr-i
C (Me)₂C≡CH NHPr-c
C (Me)₂C≡CH NHBu-n
C (Me)₂C≡CH NHBu-i
C (Me)₂C≡CH NHBu-c
C (Me)₂C≡CH NHBu-s
C (Me)₂C≡CH NHBu-t
C (Me)₂C≡CH NHPen-n
C (Me)₂C≡CH NHPen-c
C (Me)₂C≡CH NHHex-n
C (Me)₂C≡CH NHHex-c
C (Me)₂C≡CH NHCH₂CF_Three
C (Me)₂C≡CH NMe₂
C (Me)₂C≡CH N (Me) Et
C (Me)₂C≡CH N (Me) Pr-n
C (Me)₂C≡CH N (Me) Pr-i
C (Me)₂C≡CH N (Me) Pr-c
C (Me)₂C≡CH N (Me) Bu-n
C (Me)₂C≡CH N (Me) Bu-i
C (Me)₂C≡CH N (Me) Bu-c
C (Me)₂C≡CH N (Me) Bu-s
C (Me)₂C≡CH N (Me) Bu-t
C (Me)₂C≡CH N (Me) Pen-n
C (Me)₂C≡CH N (Me) Pen-c
C (Me)₂C≡CH N (Me) Hex-n
C (Me)₂C≡CH N (Me) Hex-c
C (Me)₂C≡CH N (Me) CH₂CF_Three
CH₂OCH₂C≡CH OMe
CH₂OCH₂C≡CH OEt
CH₂OCH₂C≡CH OPr-n
CH₂OCH₂C≡CH OPr-i
CH₂OCH₂C≡CH OPr-c
CH₂OCH₂C≡CH OBu-n
CH₂OCH₂C≡CH OBu-i
CH₂OCH₂C≡CH OBu-c
CH₂OCH₂C≡CH OBu-s
CH₂OCH₂C≡CH OBu-t
CH₂OCH₂C≡CH OPen-n
CH₂OCH₂C≡CH OPen-c
CH₂OCH₂C≡CH OHex-n
CH₂OCH₂C≡CH OHex-c
CH₂OCH₂C≡CH Me
CH₂OCH₂C≡CH Et
CH₂OCH₂C≡CH Pr-n
CH₂OCH₂C≡CH Pr-i
CH₂OCH₂C≡CH Pr-c
CH₂OCH₂C≡CH Bu-n
CH₂OCH₂C≡CH Bu-i
CH₂OCH₂C≡CH Bu-c
CH₂OCH₂C≡CH Bu-s
CH₂OCH₂C≡CH Bu-t
CH₂OCH₂C≡CH Pen-n
CH₂OCH₂C≡CH Pen-c
CH₂OCH₂C≡CH Hex-n
CH₂OCH₂C≡CH Hex-c
CH₂OCH₂C≡CH CH₂SMe
CH₂OCH₂C≡CH CH₂S (O) Me
CH₂OCH₂C≡CH CH₂S (O)₂Me
CH₂OCH₂C≡CH CH₂SEt
CH₂OCH₂C≡CH CH₂S (O) Et
CH₂OCH₂C≡CH CH₂S (O)₂Et
CH₂OCH₂C≡CH CH (Me) SMe
CH₂OCH₂C≡CH CH (Me) S (O) Me
CH₂OCH₂C≡CH CH (Me) S (O)₂Me
CH₂OCH₂C≡CH CH (Me) SEt
CH₂OCH₂C≡CH CH (Me) S (O) Et
CH₂OCH₂C≡CH CH (Me) S (O)₂Et
CH₂OCH₂C≡CH C (Me)₂SMe
CH₂OCH₂C≡CH C (Me)₂S (O) Me
CH₂OCH₂C≡CH C (Me)₂S (O)₂Me
CH₂OCH₂C≡CH C (Me)₂SEt
CH₂OCH₂C≡CH C (Me)₂S (O) Et
CH₂OCH₂C≡CH C (Me)₂S (O)₂Et
CH₂OCH₂C≡CH CH₂CH₂SMe
CH₂OCH₂C≡CH CH₂CH₂S (O) Me
CH₂OCH₂C≡CH CH₂CH₂S (O)₂Me
CH₂OCH₂C≡CH CH (Me) CH₂SMe
CH₂OCH₂C≡CH CH (Me) CH₂S (O) Me
CH₂OCH₂C≡CH CH (Me) CH₂S (O)₂Me
CH₂OCH₂C≡CH C (Me)₂CH₂SMe
CH₂OCH₂C≡CH C (Me)₂CH₂S (O) Me
CH₂OCH₂C≡CH C (Me)₂CH₂S (O)₂Me
CH₂OCH₂C≡CH CH₂CH (Me) SMe
CH₂OCH₂C≡CH CH₂CH (Me) S (O) Me
CH₂OCH₂C≡CH CH₂CH (Me) S (O)₂Me
CH₂OCH₂C≡CH CH₂C (Me)₂SMe
CH₂OCH₂C≡CH CH₂C (Me)₂S (O) Me
CH₂OCH₂C≡CH CH₂C (Me)₂S (O)₂Me
CH₂OCH₂C≡CH CH (Me) CH (Me) SMe
CH₂OCH₂C≡CH CH (Me) CH (Me) S (O) Me
CH₂OCH₂C≡CH CH (Me) CH (Me) S (O)₂Me
CH₂OCH₂C≡CH C (Me)₂CH (Me) SMe
CH₂OCH₂C≡CH C (Me)₂CH (Me) S (O) Me
CH₂OCH₂C≡CH C (Me)₂CH (Me) S (O)₂Me
CH₂OCH₂C≡CH CH (Me) C (Me)₂SMe
CH₂OCH₂C≡CH CH (Me) C (Me)₂S (O) Me
CH₂OCH₂C≡CH CH (Me) C (Me)₂S (O)₂Me
CH₂OCH₂C≡CH C (Me)₂C (Me)₂SMe
CH₂OCH₂C≡CH C (Me)₂C (Me)₂S (O) Me
CH₂OCH₂C≡CH C (Me)₂C (Me)₂S (O)₂Me
CH₂OCH₂C≡CH CH₂CF_Three
CH₂OCH₂C≡CH CH (Me) CF_Three
CH₂OCH₂C≡CH CH₂CF₂CF_Three
CH₂OCH₂C≡CH CH (Me) CF₂CF_Three
CH₂OCH₂C≡CH CH₂CH₂CF_Three
CH₂OCH₂C≡CH CH (Me) CH₂CF_Three
CH₂OCH₂C≡CH CH₂CH (Me) CF_Three
CH₂OCH₂C≡CH CH₂CH (CF_Three)₂
CH₂OCH₂C≡CH CH (Me) CH (CF_Three)₂
CH₂OCH₂C≡CH CH₂CF (CF_Three)₂
CH₂OCH₂C≡CH CH (Me) CF (CF_Three)₂
CH₂OCH₂C≡CH CH (CF_ThreeSMe
CH₂OCH₂C≡CH CH (CF_Three) S (O) Me
CH₂OCH₂C≡CH CH (CF_Three) S (O)₂Me
CH₂OCH₂C≡CH CH (CF_Three) SEt
CH₂OCH₂C≡CH CH (CF_Three) S (O) Et
CH₂OCH₂C≡CH CH (CF_Three) S (O)₂Et
CH₂OCH₂C≡CH CH (CF_Three) CH₂SMe
CH₂OCH₂C≡CH CH (CF_Three) CH₂S (O) Me
CH₂OCH₂C≡CH CH (CF_Three) CH₂S (O)₂Me
CH₂OCH₂C≡CH CH₂CH (CF_ThreeSMe
CH₂OCH₂C≡CH CH₂CH (CF_Three) S (O) Me
CH₂OCH₂C≡CH CH₂CH (CF_Three) S (O)₂Me
CH₂OCH₂C≡CH D1-81a
CH₂OCH₂C≡CH D1-82a
CH₂OCH₂C≡CH D1-84a
CH₂OCH₂C≡CH D1-85a
CH₂OCH₂C≡CH D1-87a
CH₂OCH₂C≡CH D1-92a
CH₂OCH₂C≡CH D1-93a
CH₂OCH₂C≡CH D1-95a
CH₂OCH₂C≡CH D1-96a
CH₂OCH₂C≡CH D1-98a
CH₂OCH₂C≡CH D1-103b
CH₂OCH₂C≡CH D1-103e
CH₂OCH₂C≡CH D1-103f
CH₂OCH₂C≡CH D1-103g
CH₂OCH₂C≡CH D1-103h
CH₂OCH₂C≡CH D1-103i
CH₂OCH₂C≡CH CH₂(D1-81a)
CH₂OCH₂C≡CH CH₂(D1-82a)
CH₂OCH₂C≡CH CH₂(D1-84a)
CH₂OCH₂C≡CH CH₂(D1-85a)
CH₂OCH₂C≡CH CH₂(D1-87a)
CH₂OCH₂C≡CH CH₂(D1-92a)
CH₂OCH₂C≡CH CH₂(D1-93a)
CH₂OCH₂C≡CH CH₂(D1-95a)
CH₂OCH₂C≡CH CH₂(D1-96a)
CH₂OCH₂C≡CH CH₂(D1-98a)
CH₂OCH₂C≡CH CH₂(D1-103b)
CH₂OCH₂C≡CH NHMe
CH₂OCH₂C≡CH NHEt
CH₂OCH₂C≡CH NHPr-n
CH₂OCH₂C≡CH NHPr-i
CH₂OCH₂C≡CH NHPr-c
CH₂OCH₂C≡CH NHBu-n
CH₂OCH₂C≡CH NHBu-i
CH₂OCH₂C≡CH NHBu-c
CH₂OCH₂C≡CH NHBu-s
CH₂OCH₂C≡CH NHBu-t
CH₂OCH₂C≡CH NHPen-n
CH₂OCH₂C≡CH NHPen-c
CH₂OCH₂C≡CH NHHex-n
CH₂OCH₂C≡CH NHHex-c
CH₂OCH₂C≡CH NHCH₂CF_Three
CH₂OCH₂C≡CH NMe₂
CH₂OCH₂C≡CH N (Me) Et
CH₂OCH₂C≡CH N (Me) Pr-n
CH₂OCH₂C≡CH N (Me) Pr-i
CH₂OCH₂C≡CH N (Me) Pr-c
CH₂OCH₂C≡CH N (Me) Bu-n
CH₂OCH₂C≡CH N (Me) Bu-i
CH₂OCH₂C≡CH N (Me) Bu-c
CH₂OCH₂C≡CH N (Me) Bu-s
CH₂OCH₂C≡CH N (Me) Bu-t
CH₂OCH₂C≡CH N (Me) Pen-n
CH₂OCH₂C≡CH N (Me) Pen-c
CH₂OCH₂C≡CH N (Me) Hex-n
CH₂OCH₂C≡CH N (Me) Hex-c
CH₂OCH₂C≡CH N (Me) CH₂CF_Three
CH₂OCH (Me) C≡CH OMe
CH₂OCH (Me) C≡CH OEt
CH₂OCH (Me) C≡CH OPr-n
CH₂OCH (Me) C≡CH OPr-i
CH₂OCH (Me) C≡CH OPr-c
CH₂OCH (Me) C≡CH OBu-n
CH₂OCH (Me) C≡CH OBu-i
CH₂OCH (Me) C≡CH OBu-c
CH₂OCH (Me) C≡CH OBu-s
CH₂OCH (Me) C≡CH OBu-t
CH₂OCH (Me) C≡CH OPen-n
CH₂OCH (Me) C≡CH OPen-c
CH₂OCH (Me) C≡CH OHex-n
CH₂OCH (Me) C≡CH OHex-c
CH₂OCH (Me) C≡CH Me
CH₂OCH (Me) C≡CH Et
CH₂OCH (Me) C≡CH Pr-n
CH₂OCH (Me) C≡CH Pr-i
CH₂OCH (Me) C≡CH Pr-c
CH₂OCH (Me) C≡CH Bu-n
CH₂OCH (Me) C≡CH Bu-i
CH₂OCH (Me) C≡CH Bu-c
CH₂OCH (Me) C≡CH Bu-s
CH₂OCH (Me) C≡CH Bu-t
CH₂OCH (Me) C≡CH Pen-n
CH₂OCH (Me) C≡CH Pen-c
CH₂OCH (Me) C≡CH Hex-n
CH₂OCH (Me) C≡CH Hex-c
CH₂OCH (Me) C≡CH CH₂SMe
CH₂OCH (Me) C≡CH CH₂S (O) Me
CH₂OCH (Me) C≡CH CH₂S (O)₂Me
CH₂OCH (Me) C≡CH CH₂SEt
CH₂OCH (Me) C≡CH CH₂S (O) Et
CH₂OCH (Me) C≡CH CH₂S (O)₂Et
CH₂OCH (Me) C≡CH CH (Me) SMe
CH₂OCH (Me) C≡CH CH (Me) S (O) Me
CH₂OCH (Me) C≡CH CH (Me) S (O)₂Me
CH₂OCH (Me) C≡CH CH (Me) SEt
CH₂OCH (Me) C≡CH CH (Me) S (O) Et
CH₂OCH (Me) C≡CH CH (Me) S (O)₂Et
CH₂OCH (Me) C≡CH C (Me)₂SMe
CH₂OCH (Me) C≡CH C (Me)₂S (O) Me
CH₂OCH (Me) C≡CH C (Me)₂S (O)₂Me
CH₂OCH (Me) C≡CH C (Me)₂SEt
CH₂OCH (Me) C≡CH C (Me)₂S (O) Et
CH₂OCH (Me) C≡CH C (Me)₂S (O)₂Et
CH₂OCH (Me) C≡CH CH₂CH₂SMe
CH₂OCH (Me) C≡CH CH₂CH₂S (O) Me
CH₂OCH (Me) C≡CH CH₂CH₂S (O)₂Me
CH₂OCH (Me) C≡CH CH (Me) CH₂SMe
CH₂OCH (Me) C≡CH CH (Me) CH₂S (O) Me
CH₂OCH (Me) C≡CH CH (Me) CH₂S (O)₂Me
CH₂OCH (Me) C≡CH C (Me)₂CH₂SMe
CH₂OCH (Me) C≡CH C (Me)₂CH₂S (O) Me
CH₂OCH (Me) C≡CH C (Me)₂CH₂S (O)₂Me
CH₂OCH (Me) C≡CH CH₂CH (Me) SMe
CH₂OCH (Me) C≡CH CH₂CH (Me) S (O) Me
CH₂OCH (Me) C≡CH CH₂CH (Me) S (O)₂Me
CH₂OCH (Me) C≡CH CH₂C (Me)₂SMe
CH₂OCH (Me) C≡CH CH₂C (Me)₂S (O) Me
CH₂OCH (Me) C≡CH CH₂C (Me)₂S (O)₂Me
CH₂OCH (Me) C≡CH CH (Me) CH (Me) SMe
CH₂OCH (Me) C≡CH CH (Me) CH (Me) S (O) Me
CH₂OCH (Me) C≡CH CH (Me) CH (Me) S (O)₂Me
CH₂OCH (Me) C≡CH C (Me)₂CH (Me) SMe
CH₂OCH (Me) C≡CH C (Me)₂CH (Me) S (O) Me
CH₂OCH (Me) C≡CH C (Me)₂CH (Me) S (O)₂Me
CH₂OCH (Me) C≡CH CH (Me) C (Me)₂SMe
CH₂OCH (Me) C≡CH CH (Me) C (Me)₂S (O) Me
CH₂OCH (Me) C≡CH CH (Me) C (Me)₂S (O)₂Me
CH₂OCH (Me) C≡CH C (Me)₂C (Me)₂SMe
CH₂OCH (Me) C≡CH C (Me)₂C (Me)₂S (O) Me
CH₂OCH (Me) C≡CH C (Me)₂C (Me)₂S (O)₂Me
CH₂OCH (Me) C≡CH CH₂CF_Three
CH₂OCH (Me) C≡CH CH (Me) CF_Three
CH₂OCH (Me) C≡CH CH₂CF₂CF_Three
CH₂OCH (Me) C≡CH CH (Me) CF₂CF_Three
CH₂OCH (Me) C≡CH CH₂CH₂CF_Three
CH₂OCH (Me) C≡CH CH (Me) CH₂CF_Three
CH₂OCH (Me) C≡CH CH₂CH (Me) CF_Three
CH₂OCH (Me) C≡CH CH₂CH (CF_Three)₂
CH₂OCH (Me) C≡CH CH (Me) CH (CF_Three)₂
CH₂OCH (Me) C≡CH CH₂CF (CF_Three)₂
CH₂OCH (Me) C≡CH CH (Me) CF (CF_Three)₂
CH₂OCH (Me) C≡CH CH (CF_ThreeSMe
CH₂OCH (Me) C≡CH CH (CF_Three) S (O) Me
CH₂OCH (Me) C≡CH CH (CF_Three) S (O)₂Me
CH₂OCH (Me) C≡CH CH (CF_Three) SEt
CH₂OCH (Me) C≡CH CH (CF_Three) S (O) Et
CH₂OCH (Me) C≡CH CH (CF_Three) S (O)₂Et
CH₂OCH (Me) C≡CH CH (CF_Three) CH₂SMe
CH₂OCH (Me) C≡CH CH (CF_Three) CH₂S (O) Me
CH₂OCH (Me) C≡CH CH (CF_Three) CH₂S (O)₂Me
CH₂OCH (Me) C≡CH CH₂CH (CF_ThreeSMe
CH₂OCH (Me) C≡CH CH₂CH (CF_Three) S (O) Me
CH₂OCH (Me) C≡CH CH₂CH (CF_Three) S (O)₂Me
CH₂OCH (Me) C≡CH D1-81a
CH₂OCH (Me) C≡CH D1-82a
CH₂OCH (Me) C≡CH D1-84a
CH₂OCH (Me) C≡CH D1-85a
CH₂OCH (Me) C≡CH D1-87a
CH₂OCH (Me) C≡CH D1-92a
CH₂OCH (Me) C≡CH D1-93a
CH₂OCH (Me) C≡CH D1-95a
CH₂OCH (Me) C≡CH D1-96a
CH₂OCH (Me) C≡CH D1-98a
CH₂OCH (Me) C≡CH D1-103b
CH₂OCH (Me) C≡CH D1-103e
CH₂OCH (Me) C≡CH D1-103f
CH₂OCH (Me) C≡CH D1-103g
CH₂OCH (Me) C≡CH D1-103h
CH₂OCH (Me) C≡CH D1-103i
CH₂OCH (Me) C≡CH CH₂(D1-81a)
CH₂OCH (Me) C≡CH CH₂(D1-82a)
CH₂OCH (Me) C≡CH CH₂(D1-84a)
CH₂OCH (Me) C≡CH CH₂(D1-85a)
CH₂OCH (Me) C≡CH CH₂(D1-87a)
CH₂OCH (Me) C≡CH CH₂(D1-92a)
CH₂OCH (Me) C≡CH CH₂(D1-93a)
CH₂OCH (Me) C≡CH CH₂(D1-95a)
CH₂OCH (Me) C≡CH CH₂(D1-96a)
CH₂OCH (Me) C≡CH CH₂(D1-98a)
CH₂OCH (Me) C≡CH CH₂(D1-103b)
CH₂OCH (Me) C≡CH NHMe
CH₂OCH (Me) C≡CH NHEt
CH₂OCH (Me) C≡CH NHPr-n
CH₂OCH (Me) C≡CH NHPr-i
CH₂OCH (Me) C≡CH NHPr-c
CH₂OCH (Me) C≡CH NHBu-n
CH₂OCH (Me) C≡CH NHBu-i
CH₂OCH (Me) C≡CH NHBu-c
CH₂OCH (Me) C≡CH NHBu-s
CH₂OCH (Me) C≡CH NHBu-t
CH₂OCH (Me) C≡CH NHPen-n
CH₂OCH (Me) C≡CH NHPen-c
CH₂OCH (Me) C≡CH NHHex-n
CH₂OCH (Me) C≡CH NHHex-c
CH₂OCH (Me) C≡CH NHCH₂CF_Three
CH₂OCH (Me) C≡CH NMe₂
CH₂OCH (Me) C≡CH N (Me) Et
CH₂OCH (Me) C≡CH N (Me) Pr-n
CH₂OCH (Me) C≡CH N (Me) Pr-i
CH₂OCH (Me) C≡CH N (Me) Pr-c
CH₂OCH (Me) C≡CH N (Me) Bu-n
CH₂OCH (Me) C≡CH N (Me) Bu-i
CH₂OCH (Me) C≡CH N (Me) Bu-c
CH₂OCH (Me) C≡CH N (Me) Bu-s
CH₂OCH (Me) C≡CH N (Me) Bu-t
CH₂OCH (Me) C≡CH N (Me) Pen-n
CH₂OCH (Me) C≡CH N (Me) Pen-c
CH₂OCH (Me) C≡CH N (Me) Hex-n
CH₂OCH (Me) C≡CH N (Me) Hex-c
CH₂OCH (Me) C≡CH N (Me) CH₂CF_Three
CH₂OC (Me)₂C≡CH OMe
CH₂OC (Me)₂C≡CH OEt
CH₂OC (Me)₂C≡CH OPr-n
CH₂OC (Me)₂C≡CH OPr-i
CH₂OC (Me)₂C≡CH OPr-c
CH₂OC (Me)₂C≡CH OBu-n
CH₂OC (Me)₂C≡CH OBu-i
CH₂OC (Me)₂C≡CH OBu-c
CH₂OC (Me)₂C≡CH OBu-s
CH₂OC (Me)₂C≡CH OBu-t
CH₂OC (Me)₂C≡CH OPen-n
CH₂OC (Me)₂C≡CH OPen-c
CH₂OC (Me)₂C≡CH OHex-n
CH₂OC (Me)₂C≡CH OHex-c
CH₂OC (Me)₂C≡CH Me
CH₂OC (Me)₂C≡CH Et
CH₂OC (Me)₂C≡CH Pr-n
CH₂OC (Me)₂C≡CH Pr-i
CH₂OC (Me)₂C≡CH Pr-c
CH₂OC (Me)₂C≡CH Bu-n
CH₂OC (Me)₂C≡CH Bu-i
CH₂OC (Me)₂C≡CH Bu-c
CH₂OC (Me)₂C≡CH Bu-s
CH₂OC (Me)₂C≡CH Bu-t
CH₂OC (Me)₂C≡CH Pen-n
CH₂OC (Me)₂C≡CH Pen-c
CH₂OC (Me)₂C≡CH Hex-n
CH₂OC (Me)₂C≡CH Hex-c
CH₂OC (Me)₂C≡CH CH₂SMe
CH₂OC (Me)₂C≡CH CH₂S (O) Me
CH₂OC (Me)₂C≡CH CH₂S (O)₂Me
CH₂OC (Me)₂C≡CH CH₂SEt
CH₂OC (Me)₂C≡CH CH₂S (O) Et
CH₂OC (Me)₂C≡CH CH₂S (O)₂Et
CH₂OC (Me)₂C≡CH CH (Me) SMe
CH₂OC (Me)₂C≡CH CH (Me) S (O) Me
CH₂OC (Me)₂C≡CH CH (Me) S (O)₂Me
CH₂OC (Me)₂C≡CH CH (Me) SEt
CH₂OC (Me)₂C≡CH CH (Me) S (O) Et
CH₂OC (Me)₂C≡CH CH (Me) S (O)₂Et
CH₂OC (Me)₂C≡CH C (Me)₂SMe
CH₂OC (Me)₂C≡CH C (Me)₂S (O) Me
CH₂OC (Me)₂C≡CH C (Me)₂S (O)₂Me
CH₂OC (Me)₂C≡CH C (Me)₂SEt
CH₂OC (Me)₂C≡CH C (Me)₂S (O) Et
CH₂OC (Me)₂C≡CH C (Me)₂S (O)₂Et
CH₂OC (Me)₂C≡CH CH₂CH₂SMe
CH₂OC (Me)₂C≡CH CH₂CH₂S (O) Me
CH₂OC (Me)₂C≡CH CH₂CH₂S (O)₂Me
CH₂OC (Me)₂C≡CH CH (Me) CH₂SMe
CH₂OC (Me)₂C≡CH CH (Me) CH₂S (O) Me
CH₂OC (Me)₂C≡CH CH (Me) CH₂S (O)₂Me
CH₂OC (Me)₂C≡CH C (Me)₂CH₂SMe
CH₂OC (Me)₂C≡CH C (Me)₂CH₂S (O) Me
CH₂OC (Me)₂C≡CH C (Me)₂CH₂S (O)₂Me
CH₂OC (Me)₂C≡CH CH₂CH (Me) SMe
CH₂OC (Me)₂C≡CH CH₂CH (Me) S (O) Me
CH₂OC (Me)₂C≡CH CH₂CH (Me) S (O)₂Me
CH₂OC (Me)₂C≡CH CH₂C (Me)₂SMe
CH₂OC (Me)₂C≡CH CH₂C (Me)₂S (O) Me
CH₂OC (Me)₂C≡CH CH₂C (Me)₂S (O)₂Me
CH₂OC (Me)₂C≡CH CH (Me) CH (Me) SMe
CH₂OC (Me)₂C≡CH CH (Me) CH (Me) S (O) Me
CH₂OC (Me)₂C≡CH CH (Me) CH (Me) S (O)₂Me
CH₂OC (Me)₂C≡CH C (Me)₂CH (Me) SMe
CH₂OC (Me)₂C≡CH C (Me)₂CH (Me) S (O) Me
CH₂OC (Me)₂C≡CH C (Me)₂CH (Me) S (O)₂Me
CH₂OC (Me)₂C≡CH CH (Me) C (Me)₂SMe
CH₂OC (Me)₂C≡CH CH (Me) C (Me)₂S (O) Me
CH₂OC (Me)₂C≡CH CH (Me) C (Me)₂S (O)₂Me
CH₂OC (Me)₂C≡CH C (Me)₂C (Me)₂SMe
CH₂OC (Me)₂C≡CH C (Me)₂C (Me)₂S (O) Me
CH₂OC (Me)₂C≡CH C (Me)₂C (Me)₂S (O)₂Me
CH₂OC (Me)₂C≡CH CH₂CF_Three
CH₂OC (Me)₂C≡CH CH (Me) CF_Three
CH₂OC (Me)₂C≡CH CH₂CF₂CF_Three
CH₂OC (Me)₂C≡CH CH (Me) CF₂CF_Three
CH₂OC (Me)₂C≡CH CH₂CH₂CF_Three
CH₂OC (Me)₂C≡CH CH (Me) CH₂CF_Three
CH₂OC (Me)₂C≡CH CH₂CH (Me) CF_Three
CH₂OC (Me)₂C≡CH CH₂CH (CF_Three)₂
CH₂OC (Me)₂C≡CH CH (Me) CH (CF_Three)₂
CH₂OC (Me)₂C≡CH CH₂CF (CF_Three)₂
CH₂OC (Me)₂C≡CH CH (Me) CF (CF_Three)₂
CH₂OC (Me)₂C≡CH CH (CF_ThreeSMe
CH₂OC (Me)₂C≡CH CH (CF_Three) S (O) Me
CH₂OC (Me)₂C≡CH CH (CF_Three) S (O)₂Me
CH₂OC (Me)₂C≡CH CH (CF_Three) SEt
CH₂OC (Me)₂C≡CH CH (CF_Three) S (O) Et
CH₂OC (Me)₂C≡CH CH (CF_Three) S (O)₂Et
CH₂OC (Me)₂C≡CH CH (CF_Three) CH₂SMe
CH₂OC (Me)₂C≡CH CH (CF_Three) CH₂S (O) Me
CH₂OC (Me)₂C≡CH CH (CF_Three) CH₂S (O)₂Me
CH₂OC (Me)₂C≡CH CH₂CH (CF_ThreeSMe
CH₂OC (Me)₂C≡CH CH₂CH (CF_Three) S (O) Me
CH₂OC (Me)₂C≡CH CH₂CH (CF_Three) S (O)₂Me
CH₂OC (Me)₂C≡CH D1-81a
CH₂OC (Me)₂C≡CH D1-82a
CH₂OC (Me)₂C≡CH D1-84a
CH₂OC (Me)₂C≡CH D1-85a
CH₂OC (Me)₂C≡CH D1-87a
CH₂OC (Me)₂C≡CH D1-92a
CH₂OC (Me)₂C≡CH D1-93a
CH₂OC (Me)₂C≡CH D1-95a
CH₂OC (Me)₂C≡CH D1-96a
CH₂OC (Me)₂C≡CH D1-98a
CH₂OC (Me)₂C≡CH D1-103b
CH₂OC (Me)₂C≡CH D1-103e
CH₂OC (Me)₂C≡CH D1-103f
CH₂OC (Me)₂C≡CH D1-103g
CH₂OC (Me)₂C≡CH D1-103h
CH₂OC (Me)₂C≡CH D1-103i
CH₂OC (Me)₂C≡CH CH₂(D1-81a)
CH₂OC (Me)₂C≡CH CH₂(D1-82a)
CH₂OC (Me)₂C≡CH CH₂(D1-84a)
CH₂OC (Me)₂C≡CH CH₂(D1-85a)
CH₂OC (Me)₂C≡CH CH₂(D1-87a)
CH₂OC (Me)₂C≡CH CH₂(D1-92a)
CH₂OC (Me)₂C≡CH CH₂(D1-93a)
CH₂OC (Me)₂C≡CH CH₂(D1-95a)
CH₂OC (Me)₂C≡CH CH₂(D1-96a)
CH₂OC (Me)₂C≡CH CH₂(D1-98a)
CH₂OC (Me)₂C≡CH CH₂(D1-103b)
CH₂OC (Me)₂C≡CH NHMe
CH₂OC (Me)₂C≡CH NHEt
CH₂OC (Me)₂C≡CH NHPr-n
CH₂OC (Me)₂C≡CH NHPr-i
CH₂OC (Me)₂C≡CH NHPr-c
CH₂OC (Me)₂C≡CH NHBu-n
CH₂OC (Me)₂C≡CH NHBu-i
CH₂OC (Me)₂C≡CH NHBu-c
CH₂OC (Me)₂C≡CH NHBu-s
CH₂OC (Me)₂C≡CH NHBu-t
CH₂OC (Me)₂C≡CH NHPen-n
CH₂OC (Me)₂C≡CH NHPen-c
CH₂OC (Me)₂C≡CH NHHex-n
CH₂OC (Me)₂C≡CH NHHex-c
CH₂OC (Me)₂C≡CH NHCH₂CF_Three
CH₂OC (Me)₂C≡CH NMe₂
CH₂OC (Me)₂C≡CH N (Me) Et
CH₂OC (Me)₂C≡CH N (Me) Pr-n
CH₂OC (Me)₂C≡CH N (Me) Pr-i
CH₂OC (Me)₂C≡CH N (Me) Pr-c
CH₂OC (Me)₂C≡CH N (Me) Bu-n
CH₂OC (Me)₂C≡CH N (Me) Bu-i
CH₂OC (Me)₂C≡CH N (Me) Bu-c
CH₂OC (Me)₂C≡CH N (Me) Bu-s
CH₂OC (Me)₂C≡CH N (Me) Bu-t
CH₂OC (Me)₂C≡CH N (Me) Pen-n
CH₂OC (Me)₂C≡CH N (Me) Pen-c
CH₂OC (Me)₂C≡CH N (Me) Hex-n
CH₂OC (Me)₂C≡CH N (Me) Hex-c
CH₂OC (Me)₂C≡CH N (Me) CH₂CF_Three
CH (Me) OCH₂C≡CH OMe
CH (Me) OCH₂C≡CH OEt
CH (Me) OCH₂C≡CH OPr-n
CH (Me) OCH₂C≡CH OPr-i
CH (Me) OCH₂C≡CH OPr-c
CH (Me) OCH₂C≡CH OBu-n
CH (Me) OCH₂C≡CH OBu-i
CH (Me) OCH₂C≡CH OBu-c
CH (Me) OCH₂C≡CH OBu-s
CH (Me) OCH₂C≡CH OBu-t
CH (Me) OCH₂C≡CH OPen-n
CH (Me) OCH₂C≡CH OPen-c
CH (Me) OCH₂C≡CH OHex-n
CH (Me) OCH₂C≡CH OHex-c
CH (Me) OCH₂C≡CH Me
CH (Me) OCH₂C≡CH Et
CH (Me) OCH₂C≡CH Pr-n
CH (Me) OCH₂C≡CH Pr-i
CH (Me) OCH₂C≡CH Pr-c
CH (Me) OCH₂C≡CH Bu-n
CH (Me) OCH₂C≡CH Bu-i
CH (Me) OCH₂C≡CH Bu-c
CH (Me) OCH₂C≡CH Bu-s
CH (Me) OCH₂C≡CH Bu-t
CH (Me) OCH₂C≡CH Pen-n
CH (Me) OCH₂C≡CH Pen-c
CH (Me) OCH₂C≡CH Hex-n
CH (Me) OCH₂C≡CH Hex-c
CH (Me) OCH₂C≡CH CH₂SMe
CH (Me) OCH₂C≡CH CH₂S (O) Me
CH (Me) OCH₂C≡CH CH₂S (O)₂Me
CH (Me) OCH₂C≡CH CH₂SEt
CH (Me) OCH₂C≡CH CH₂S (O) Et
CH (Me) OCH₂C≡CH CH₂S (O)₂Et
CH (Me) OCH₂C≡CH CH (Me) SMe
CH (Me) OCH₂C≡CH CH (Me) S (O) Me
CH (Me) OCH₂C≡CH CH (Me) S (O)₂Me
CH (Me) OCH₂C≡CH CH (Me) SEt
CH (Me) OCH₂C≡CH CH (Me) S (O) Et
CH (Me) OCH₂C≡CH CH (Me) S (O)₂Et
CH (Me) OCH₂C≡CH C (Me)₂SMe
CH (Me) OCH₂C≡CH C (Me)₂S (O) Me
CH (Me) OCH₂C≡CH C (Me)₂S (O)₂Me
CH (Me) OCH₂C≡CH C (Me)₂SEt
CH (Me) OCH₂C≡CH C (Me)₂S (O) Et
CH (Me) OCH₂C≡CH C (Me)₂S (O)₂Et
CH (Me) OCH₂C≡CH CH₂CH₂SMe
CH (Me) OCH₂C≡CH CH₂CH₂S (O) Me
CH (Me) OCH₂C≡CH CH₂CH₂S (O)₂Me
CH (Me) OCH₂C≡CH CH (Me) CH₂SMe
CH (Me) OCH₂C≡CH CH (Me) CH₂S (O) Me
CH (Me) OCH₂C≡CH CH (Me) CH₂S (O)₂Me
CH (Me) OCH₂C≡CH C (Me)₂CH₂SMe
CH (Me) OCH₂C≡CH C (Me)₂CH₂S (O) Me
CH (Me) OCH₂C≡CH C (Me)₂CH₂S (O)₂Me
CH (Me) OCH₂C≡CH CH₂CH (Me) SMe
CH (Me) OCH₂C≡CH CH₂CH (Me) S (O) Me
CH (Me) OCH₂C≡CH CH₂CH (Me) S (O)₂Me
CH (Me) OCH₂C≡CH CH₂C (Me)₂SMe
CH (Me) OCH₂C≡CH CH₂C (Me)₂S (O) Me
CH (Me) OCH₂C≡CH CH₂C (Me)₂S (O)₂Me
CH (Me) OCH₂C≡CH CH (Me) CH (Me) SMe
CH (Me) OCH₂C≡CH CH (Me) CH (Me) S (O) Me
CH (Me) OCH₂C≡CH CH (Me) CH (Me) S (O)₂Me
CH (Me) OCH₂C≡CH C (Me)₂CH (Me) SMe
CH (Me) OCH₂C≡CH C (Me)₂CH (Me) S (O) Me
CH (Me) OCH₂C≡CH C (Me)₂CH (Me) S (O)₂Me
CH (Me) OCH₂C≡CH CH (Me) C (Me)₂SMe
CH (Me) OCH₂C≡CH CH (Me) C (Me)₂S (O) Me
CH (Me) OCH₂C≡CH CH (Me) C (Me)₂S (O)₂Me
CH (Me) OCH₂C≡CH C (Me)₂C (Me)₂SMe
CH (Me) OCH₂C≡CH C (Me)₂C (Me)₂S (O) Me
CH (Me) OCH₂C≡CH C (Me)₂C (Me)₂S (O)₂Me
CH (Me) OCH₂C≡CH CH₂CF_Three
CH (Me) OCH₂C≡CH CH (Me) CF_Three
CH (Me) OCH₂C≡CH CH₂CF₂CF_Three
CH (Me) OCH₂C≡CH CH (Me) CF₂CF_Three
CH (Me) OCH₂C≡CH CH₂CH₂CF_Three
CH (Me) OCH₂C≡CH CH (Me) CH₂CF_Three
CH (Me) OCH₂C≡CH CH₂CH (Me) CF_Three
CH (Me) OCH₂C≡CH CH₂CH (CF_Three)₂
CH (Me) OCH₂C≡CH CH (Me) CH (CF_Three)₂
CH (Me) OCH₂C≡CH CH₂CF (CF_Three)₂
CH (Me) OCH₂C≡CH CH (Me) CF (CF_Three)₂
CH (Me) OCH₂C≡CH CH (CF_ThreeSMe
CH (Me) OCH₂C≡CH CH (CF_Three) S (O) Me
CH (Me) OCH₂C≡CH CH (CF_Three) S (O)₂Me
CH (Me) OCH₂C≡CH CH (CF_Three) SEt
CH (Me) OCH₂C≡CH CH (CF_Three) S (O) Et
CH (Me) OCH₂C≡CH CH (CF_Three) S (O)₂Et
CH (Me) OCH₂C≡CH CH (CF_Three) CH₂SMe
CH (Me) OCH₂C≡CH CH (CF_Three) CH₂S (O) Me
CH (Me) OCH₂C≡CH CH (CF_Three) CH₂S (O)₂Me
CH (Me) OCH₂C≡CH CH₂CH (CF_ThreeSMe
CH (Me) OCH₂C≡CH CH₂CH (CF_Three) S (O) Me
CH (Me) OCH₂C≡CH CH₂CH (CF_Three) S (O)₂Me
CH (Me) OCH₂C≡CH D1-81a
CH (Me) OCH₂C≡CH D1-82a
CH (Me) OCH₂C≡CH D1-84a
CH (Me) OCH₂C≡CH D1-85a
CH (Me) OCH₂C≡CH D1-87a
CH (Me) OCH₂C≡CH D1-92a
CH (Me) OCH₂C≡CH D1-93a
CH (Me) OCH₂C≡CH D1-95a
CH (Me) OCH₂C≡CH D1-96a
CH (Me) OCH₂C≡CH D1-98a
CH (Me) OCH₂C≡CH D1-103b
CH (Me) OCH₂C≡CH D1-103e
CH (Me) OCH₂C≡CH D1-103f
CH (Me) OCH₂C≡CH D1-103g
CH (Me) OCH₂C≡CH D1-103h
CH (Me) OCH₂C≡CH D1-103i
CH (Me) OCH₂C≡CH CH₂(D1-81a)
CH (Me) OCH₂C≡CH CH₂(D1-82a)
CH (Me) OCH₂C≡CH CH₂(D1-84a)
CH (Me) OCH₂C≡CH CH₂(D1-85a)
CH (Me) OCH₂C≡CH CH₂(D1-87a)
CH (Me) OCH₂C≡CH CH₂(D1-92a)
CH (Me) OCH₂C≡CH CH₂(D1-93a)
CH (Me) OCH₂C≡CH CH₂(D1-95a)
CH (Me) OCH₂C≡CH CH₂(D1-96a)
CH (Me) OCH₂C≡CH CH₂(D1-98a)
CH (Me) OCH₂C≡CH CH₂(D1-103b)
CH (Me) OCH₂C≡CH NHMe
CH (Me) OCH₂C≡CH NHEt
CH (Me) OCH₂C≡CH NHPr-n
CH (Me) OCH₂C≡CH NHPr-i
CH (Me) OCH₂C≡CH NHPr-c
CH (Me) OCH₂C≡CH NHBu-n
CH (Me) OCH₂C≡CH NHBu-i
CH (Me) OCH₂C≡CH NHBu-c
CH (Me) OCH₂C≡CH NHBu-s
CH (Me) OCH₂C≡CH NHBu-t
CH (Me) OCH₂C≡CH NHPen-n
CH (Me) OCH₂C≡CH NHPen-c
CH (Me) OCH₂C≡CH NHHex-n
CH (Me) OCH₂C≡CH NHHex-c
CH (Me) OCH₂C≡CH NHCH₂CF_Three
CH (Me) OCH₂C≡CH NMe₂
CH (Me) OCH₂C≡CH N (Me) Et
CH (Me) OCH₂C≡CH N (Me) Pr-n
CH (Me) OCH₂C≡CH N (Me) Pr-i
CH (Me) OCH₂C≡CH N (Me) Pr-c
CH (Me) OCH₂C≡CH N (Me) Bu-n
CH (Me) OCH₂C≡CH N (Me) Bu-i
CH (Me) OCH₂C≡CH N (Me) Bu-c
CH (Me) OCH₂C≡CH N (Me) Bu-s
CH (Me) OCH₂C≡CH N (Me) Bu-t
CH (Me) OCH₂C≡CH N (Me) Pen-n
CH (Me) OCH₂C≡CH N (Me) Pen-c
CH (Me) OCH₂C≡CH N (Me) Hex-n
CH (Me) OCH₂C≡CH N (Me) Hex-c
CH (Me) OCH₂C≡CH N (Me) CH₂CF_Three
CH (Me) OCH (Me) C≡CH OMe
CH (Me) OCH (Me) C≡CH OEt
CH (Me) OCH (Me) C≡CH OPr-n
CH (Me) OCH (Me) C≡CH OPr-i
CH (Me) OCH (Me) C≡CH OPr-c
CH (Me) OCH (Me) C≡CH OBu-n
CH (Me) OCH (Me) C≡CH OBu-i
CH (Me) OCH (Me) C≡CH OBu-c
CH (Me) OCH (Me) C≡CH OBu-s
CH (Me) OCH (Me) C≡CH OBu-t
CH (Me) OCH (Me) C≡CH OPen-n
CH (Me) OCH (Me) C≡CH OPen-c
CH (Me) OCH (Me) C≡CH OHex-n
CH (Me) OCH (Me) C≡CH OHex-c
CH (Me) OCH (Me) C≡CH Me
CH (Me) OCH (Me) C≡CH Et
CH (Me) OCH (Me) C≡CH Pr-n
CH (Me) OCH (Me) C≡CH Pr-i
CH (Me) OCH (Me) C≡CH Pr-c
CH (Me) OCH (Me) C≡CH Bu-n
CH (Me) OCH (Me) C≡CH Bu-i
CH (Me) OCH (Me) C≡CH Bu-c
CH (Me) OCH (Me) C≡CH Bu-s
CH (Me) OCH (Me) C≡CH Bu-t
CH (Me) OCH (Me) C≡CH Pen-n
CH (Me) OCH (Me) C≡CH Pen-c
CH (Me) OCH (Me) C≡CH Hex-n
CH (Me) OCH (Me) C≡CH Hex-c
CH (Me) OCH (Me) C≡CH CH₂SMe
CH (Me) OCH (Me) C≡CH CH₂S (O) Me
CH (Me) OCH (Me) C≡CH CH₂S (O)₂Me
CH (Me) OCH (Me) C≡CH CH₂SEt
CH (Me) OCH (Me) C≡CH CH₂S (O) Et
CH (Me) OCH (Me) C≡CH CH₂S (O)₂Et
CH (Me) OCH (Me) C≡CH CH (Me) SMe
CH (Me) OCH (Me) C≡CH CH (Me) S (O) Me
CH (Me) OCH (Me) C≡CH CH (Me) S (O)₂Me
CH (Me) OCH (Me) C≡CH CH (Me) SEt
CH (Me) OCH (Me) C≡CH CH (Me) S (O) Et
CH (Me) OCH (Me) C≡CH CH (Me) S (O)₂Et
CH (Me) OCH (Me) C≡CH C (Me)₂SMe
CH (Me) OCH (Me) C≡CH C (Me)₂S (O) Me
CH (Me) OCH (Me) C≡CH C (Me)₂S (O)₂Me
CH (Me) OCH (Me) C≡CH C (Me)₂SEt
CH (Me) OCH (Me) C≡CH C (Me)₂S (O) Et
CH (Me) OCH (Me) C≡CH C (Me)₂S (O)₂Et
CH (Me) OCH (Me) C≡CH CH₂CH₂SMe
CH (Me) OCH (Me) C≡CH CH₂CH₂S (O) Me
CH (Me) OCH (Me) C≡CH CH₂CH₂S (O)₂Me
CH (Me) OCH (Me) C≡CH CH (Me) CH₂SMe
CH (Me) OCH (Me) C≡CH CH (Me) CH₂S (O) Me
CH (Me) OCH (Me) C≡CH CH (Me) CH₂S (O)₂Me
CH (Me) OCH (Me) C≡CH C (Me)₂CH₂SMe
CH (Me) OCH (Me) C≡CH C (Me)₂CH₂S (O) Me
CH (Me) OCH (Me) C≡CH C (Me)₂CH₂S (O)₂Me
CH (Me) OCH (Me) C≡CH CH₂CH (Me) SMe
CH (Me) OCH (Me) C≡CH CH₂CH (Me) S (O) Me
CH (Me) OCH (Me) C≡CH CH₂CH (Me) S (O)₂Me
CH (Me) OCH (Me) C≡CH CH₂C (Me)₂SMe
CH (Me) OCH (Me) C≡CH CH₂C (Me)₂S (O) Me
CH (Me) OCH (Me) C≡CH CH₂C (Me)₂S (O)₂Me
CH (Me) OCH (Me) C≡CH CH (Me) CH (Me) SMe
CH (Me) OCH (Me) C≡CH CH (Me) CH (Me) S (O) Me
CH (Me) OCH (Me) C≡CH CH (Me) CH (Me) S (O)₂Me
CH (Me) OCH (Me) C≡CH C (Me)₂CH (Me) SMe
CH (Me) OCH (Me) C≡CH C (Me)₂CH (Me) S (O) Me
CH (Me) OCH (Me) C≡CH C (Me)₂CH (Me) S (O)₂Me
CH (Me) OCH (Me) C≡CH CH (Me) C (Me)₂SMe
CH (Me) OCH (Me) C≡CH CH (Me) C (Me)₂S (O) Me
CH (Me) OCH (Me) C≡CH CH (Me) C (Me)₂S (O)₂Me
CH (Me) OCH (Me) C≡CH C (Me)₂C (Me)₂SMe
CH (Me) OCH (Me) C≡CH C (Me)₂C (Me)₂S (O) Me
CH (Me) OCH (Me) C≡CH C (Me)₂C (Me)₂S (O)₂Me
CH (Me) OCH (Me) C≡CH CH₂CF_Three
CH (Me) OCH (Me) C≡CH CH (Me) CF_Three
CH (Me) OCH (Me) C≡CH CH₂CF₂CF_Three
CH (Me) OCH (Me) C≡CH CH (Me) CF₂CF_Three
CH (Me) OCH (Me) C≡CH CH₂CH₂CF_Three
CH (Me) OCH (Me) C≡CH CH (Me) CH₂CF_Three
CH (Me) OCH (Me) C≡CH CH₂CH (Me) CF_Three
CH (Me) OCH (Me) C≡CH CH₂CH (CF_Three)₂
CH (Me) OCH (Me) C≡CH CH (Me) CH (CF_Three)₂
CH (Me) OCH (Me) C≡CH CH₂CF (CF_Three)₂
CH (Me) OCH (Me) C≡CH CH (Me) CF (CF_Three)₂
CH (Me) OCH (Me) C≡CH CH (CF_ThreeSMe
CH (Me) OCH (Me) C≡CH CH (CF_Three) S (O) Me
CH (Me) OCH (Me) C≡CH CH (CF_Three) S (O)₂Me
CH (Me) OCH (Me) C≡CH CH (CF_Three) SEt
CH (Me) OCH (Me) C≡CH CH (CF_Three) S (O) Et
CH (Me) OCH (Me) C≡CH CH (CF_Three) S (O)₂Et
CH (Me) OCH (Me) C≡CH CH (CF_Three) CH₂SMe
CH (Me) OCH (Me) C≡CH CH (CF_Three) CH₂S (O) Me
CH (Me) OCH (Me) C≡CH CH (CF_Three) CH₂S (O)₂Me
CH (Me) OCH (Me) C≡CH CH₂CH (CF_ThreeSMe
CH (Me) OCH (Me) C≡CH CH₂CH (CF_Three) S (O) Me
CH (Me) OCH (Me) C≡CH CH₂CH (CF_Three) S (O)₂Me
CH (Me) OCH (Me) C≡CH D1-81a
CH (Me) OCH (Me) C≡CH D1-82a
CH (Me) OCH (Me) C≡CH D1-84a
CH (Me) OCH (Me) C≡CH D1-85a
CH (Me) OCH (Me) C≡CH D1-87a
CH (Me) OCH (Me) C≡CH D1-92a
CH (Me) OCH (Me) C≡CH D1-93a
CH (Me) OCH (Me) C≡CH D1-95a
CH (Me) OCH (Me) C≡CH D1-96a
CH (Me) OCH (Me) C≡CH D1-98a
CH (Me) OCH (Me) C≡CH D1-103b
CH (Me) OCH (Me) C≡CH D1-103e
CH (Me) OCH (Me) C≡CH D1-103f
CH (Me) OCH (Me) C≡CH D1-103g
CH (Me) OCH (Me) C≡CH D1-103h
CH (Me) OCH (Me) C≡CH D1-103i
CH (Me) OCH (Me) C≡CH CH₂(D1-81a)
CH (Me) OCH (Me) C≡CH CH₂(D1-82a)
CH (Me) OCH (Me) C≡CH CH₂(D1-84a)
CH (Me) OCH (Me) C≡CH CH₂(D1-85a)
CH (Me) OCH (Me) C≡CH CH₂(D1-87a)
CH (Me) OCH (Me) C≡CH CH₂(D1-92a)
CH (Me) OCH (Me) C≡CH CH₂(D1-93a)
CH (Me) OCH (Me) C≡CH CH₂(D1-95a)
CH (Me) OCH (Me) C≡CH CH₂(D1-96a)
CH (Me) OCH (Me) C≡CH CH₂(D1-98a)
CH (Me) OCH (Me) C≡CH CH₂(D1-103b)
CH (Me) OCH (Me) C≡CH NHMe
CH (Me) OCH (Me) C≡CH NHEt
CH (Me) OCH (Me) C≡CH NHPr-n
CH (Me) OCH (Me) C≡CH NHPr-i
CH (Me) OCH (Me) C≡CH NHPr-c
CH (Me) OCH (Me) C≡CH NHBu-n
CH (Me) OCH (Me) C≡CH NHBu-i
CH (Me) OCH (Me) C≡CH NHBu-c
CH (Me) OCH (Me) C≡CH NHBu-s
CH (Me) OCH (Me) C≡CH NHBu-t
CH (Me) OCH (Me) C≡CH NHPen-n
CH (Me) OCH (Me) C≡CH NHPen-c
CH (Me) OCH (Me) C≡CH NHHex-n
CH (Me) OCH (Me) C≡CH NHHex-c
CH (Me) OCH (Me) C≡CH NHCH₂CF_Three
CH (Me) OCH (Me) C≡CH NMe₂
CH (Me) OCH (Me) C≡CH N (Me) Et
CH (Me) OCH (Me) C≡CH N (Me) Pr-n
CH (Me) OCH (Me) C≡CH N (Me) Pr-i
CH (Me) OCH (Me) C≡CH N (Me) Pr-c
CH (Me) OCH (Me) C≡CH N (Me) Bu-n
CH (Me) OCH (Me) C≡CH N (Me) Bu-i
CH (Me) OCH (Me) C≡CH N (Me) Bu-c
CH (Me) OCH (Me) C≡CH N (Me) Bu-s
CH (Me) OCH (Me) C≡CH N (Me) Bu-t
CH (Me) OCH (Me) C≡CH N (Me) Pen-n
CH (Me) OCH (Me) C≡CH N (Me) Pen-c
CH (Me) OCH (Me) C≡CH N (Me) Hex-n
CH (Me) OCH (Me) C≡CH N (Me) Hex-c
CH (Me) OCH (Me) C≡CH N (Me) CH₂CF_Three
CH (Me) OC (Me)₂C≡CH OMe
CH (Me) OC (Me)₂C≡CH OEt
CH (Me) OC (Me)₂C≡CH OPr-n
CH (Me) OC (Me)₂C≡CH OPr-i
CH (Me) OC (Me)₂C≡CH OPr-c
CH (Me) OC (Me)₂C≡CH OBu-n
CH (Me) OC (Me)₂C≡CH OBu-i
CH (Me) OC (Me)₂C≡CH OBu-c
CH (Me) OC (Me)₂C≡CH OBu-s
CH (Me) OC (Me)₂C≡CH OBu-t
CH (Me) OC (Me)₂C≡CH OPen-n
CH (Me) OC (Me)₂C≡CH OPen-c
CH (Me) OC (Me)₂C≡CH OHex-n
CH (Me) OC (Me)₂C≡CH OHex-c
CH (Me) OC (Me)₂C≡CH Me
CH (Me) OC (Me)₂C≡CH Et
CH (Me) OC (Me)₂C≡CH Pr-n
CH (Me) OC (Me)₂C≡CH Pr-i
CH (Me) OC (Me)₂C≡CH Pr-c
CH (Me) OC (Me)₂C≡CH Bu-n
CH (Me) OC (Me)₂C≡CH Bu-i
CH (Me) OC (Me)₂C≡CH Bu-c
CH (Me) OC (Me)₂C≡CH Bu-s
CH (Me) OC (Me)₂C≡CH Bu-t
CH (Me) OC (Me)₂C≡CH Pen-n
CH (Me) OC (Me)₂C≡CH Pen-c
CH (Me) OC (Me)₂C≡CH Hex-n
CH (Me) OC (Me)₂C≡CH Hex-c
CH (Me) OC (Me)₂C≡CH CH₂SMe
CH (Me) OC (Me)₂C≡CH CH₂S (O) Me
CH (Me) OC (Me)₂C≡CH CH₂S (O)₂Me
CH (Me) OC (Me)₂C≡CH CH₂SEt
CH (Me) OC (Me)₂C≡CH CH₂S (O) Et
CH (Me) OC (Me)₂C≡CH CH₂S (O)₂Et
CH (Me) OC (Me)₂C≡CH CH (Me) SMe
CH (Me) OC (Me)₂C≡CH CH (Me) S (O) Me
CH (Me) OC (Me)₂C≡CH CH (Me) S (O)₂Me
CH (Me) OC (Me)₂C≡CH CH (Me) SEt
CH (Me) OC (Me)₂C≡CH CH (Me) S (O) Et
CH (Me) OC (Me)₂C≡CH CH (Me) S (O)₂Et
CH (Me) OC (Me)₂C≡CH C (Me)₂SMe
CH (Me) OC (Me)₂C≡CH C (Me)₂S (O) Me
CH (Me) OC (Me)₂C≡CH C (Me)₂S (O)₂Me
CH (Me) OC (Me)₂C≡CH C (Me)₂SEt
CH (Me) OC (Me)₂C≡CH C (Me)₂S (O) Et
CH (Me) OC (Me)₂C≡CH C (Me)₂S (O)₂Et
CH (Me) OC (Me)₂C≡CH CH₂CH₂SMe
CH (Me) OC (Me)₂C≡CH CH₂CH₂S (O) Me
CH (Me) OC (Me)₂C≡CH CH₂CH₂S (O)₂Me
CH (Me) OC (Me)₂C≡CH CH (Me) CH₂SMe
CH (Me) OC (Me)₂C≡CH CH (Me) CH₂S (O) Me
CH (Me) OC (Me)₂C≡CH CH (Me) CH₂S (O)₂Me
CH (Me) OC (Me)₂C≡CH C (Me)₂CH₂SMe
CH (Me) OC (Me)₂C≡CH C (Me)₂CH₂S (O) Me
CH (Me) OC (Me)₂C≡CH C (Me)₂CH₂S (O)₂Me
CH (Me) OC (Me)₂C≡CH CH₂CH (Me) SMe
CH (Me) OC (Me)₂C≡CH CH₂CH (Me) S (O) Me
CH (Me) OC (Me)₂C≡CH CH₂CH (Me) S (O)₂Me
CH (Me) OC (Me)₂C≡CH CH₂C (Me)₂SMe
CH (Me) OC (Me)₂C≡CH CH₂C (Me)₂S (O) Me
CH (Me) OC (Me)₂C≡CH CH₂C (Me)₂S (O)₂Me
CH (Me) OC (Me)₂C≡CH CH (Me) CH (Me) SMe
CH (Me) OC (Me)₂C≡CH CH (Me) CH (Me) S (O) Me
CH (Me) OC (Me)₂C≡CH CH (Me) CH (Me) S (O)₂Me
CH (Me) OC (Me)₂C≡CH C (Me)₂CH (Me) SMe
CH (Me) OC (Me)₂C≡CH C (Me)₂CH (Me) S (O) Me
CH (Me) OC (Me)₂C≡CH C (Me)₂CH (Me) S (O)₂Me
CH (Me) OC (Me)₂C≡CH CH (Me) C (Me)₂SMe
CH (Me) OC (Me)₂C≡CH CH (Me) C (Me)₂S (O) Me
CH (Me) OC (Me)₂C≡CH CH (Me) C (Me)₂S (O)₂Me
CH (Me) OC (Me)₂C≡CH C (Me)₂C (Me)₂SMe
CH (Me) OC (Me)₂C≡CH C (Me)₂C (Me)₂S (O) Me
CH (Me) OC (Me)₂C≡CH C (Me)₂C (Me)₂S (O)₂Me
CH (Me) OC (Me)₂C≡CH CH₂CF_Three
CH (Me) OC (Me)₂C≡CH CH (Me) CF_Three
CH (Me) OC (Me)₂C≡CH CH₂CF₂CF_Three
CH (Me) OC (Me)₂C≡CH CH (Me) CF₂CF_Three
CH (Me) OC (Me)₂C≡CH CH₂CH₂CF_Three
CH (Me) OC (Me)₂C≡CH CH (Me) CH₂CF_Three
CH (Me) OC (Me)₂C≡CH CH₂CH (Me) CF_Three
CH (Me) OC (Me)₂C≡CH CH₂CH (CF_Three)₂
CH (Me) OC (Me)₂C≡CH CH (Me) CH (CF_Three)₂
CH (Me) OC (Me)₂C≡CH CH₂CF (CF_Three)₂
CH (Me) OC (Me)₂C≡CH CH (Me) CF (CF_Three)₂
CH (Me) OC (Me)₂C≡CH CH (CF_ThreeSMe
CH (Me) OC (Me)₂C≡CH CH (CF_Three) S (O) Me
CH (Me) OC (Me)₂C≡CH CH (CF_Three) S (O)₂Me
CH (Me) OC (Me)₂C≡CH CH (CF_Three) SEt
CH (Me) OC (Me)₂C≡CH CH (CF_Three) S (O) Et
CH (Me) OC (Me)₂C≡CH CH (CF_Three) S (O)₂Et
CH (Me) OC (Me)₂C≡CH CH (CF_Three) CH₂SMe
CH (Me) OC (Me)₂C≡CH CH (CF_Three) CH₂S (O) Me
CH (Me) OC (Me)₂C≡CH CH (CF_Three) CH₂S (O)₂Me
CH (Me) OC (Me)₂C≡CH CH₂CH (CF_ThreeSMe
CH (Me) OC (Me)₂C≡CH CH₂CH (CF_Three) S (O) Me
CH (Me) OC (Me)₂C≡CH CH₂CH (CF_Three) S (O)₂Me
CH (Me) OC (Me)₂C≡CH D1-81a
CH (Me) OC (Me)₂C≡CH D1-82a
CH (Me) OC (Me)₂C≡CH D1-84a
CH (Me) OC (Me)₂C≡CH D1-85a
CH (Me) OC (Me)₂C≡CH D1-87a
CH (Me) OC (Me)₂C≡CH D1-92a
CH (Me) OC (Me)₂C≡CH D1-93a
CH (Me) OC (Me)₂C≡CH D1-95a
CH (Me) OC (Me)₂C≡CH D1-96a
CH (Me) OC (Me)₂C≡CH D1-98a
CH (Me) OC (Me)₂C≡CH D1-103b
CH (Me) OC (Me)₂C≡CH D1-103e
CH (Me) OC (Me)₂C≡CH D1-103f
CH (Me) OC (Me)₂C≡CH D1-103g
CH (Me) OC (Me)₂C≡CH D1-103h
CH (Me) OC (Me)₂C≡CH D1-103i
CH (Me) OC (Me)₂C≡CH CH₂(D1-81a)
CH (Me) OC (Me)₂C≡CH CH₂(D1-82a)
CH (Me) OC (Me)₂C≡CH CH₂(D1-84a)
CH (Me) OC (Me)₂C≡CH CH₂(D1-85a)
CH (Me) OC (Me)₂C≡CH CH₂(D1-87a)
CH (Me) OC (Me)₂C≡CH CH₂(D1-92a)
CH (Me) OC (Me)₂C≡CH CH₂(D1-93a)
CH (Me) OC (Me)₂C≡CH CH₂(D1-95a)
CH (Me) OC (Me)₂C≡CH CH₂(D1-96a)
CH (Me) OC (Me)₂C≡CH CH₂(D1-98a)
CH (Me) OC (Me)₂C≡CH CH₂(D1-103b)
CH (Me) OC (Me)₂C≡CH NHMe
CH (Me) OC (Me)₂C≡CH NHEt
CH (Me) OC (Me)₂C≡CH NHPr-n
CH (Me) OC (Me)₂C≡CH NHPr-i
CH (Me) OC (Me)₂C≡CH NHPr-c
CH (Me) OC (Me)₂C≡CH NHBu-n
CH (Me) OC (Me)₂C≡CH NHBu-i
CH (Me) OC (Me)₂C≡CH NHBu-c
CH (Me) OC (Me)₂C≡CH NHBu-s
CH (Me) OC (Me)₂C≡CH NHBu-t
CH (Me) OC (Me)₂C≡CH NHPen-n
CH (Me) OC (Me)₂C≡CH NHPen-c
CH (Me) OC (Me)₂C≡CH NHHex-n
CH (Me) OC (Me)₂C≡CH NHHex-c
CH (Me) OC (Me)₂C≡CH NHCH₂CF_Three
CH (Me) OC (Me)₂C≡CH NMe₂
CH (Me) OC (Me)₂C≡CH N (Me) Et
CH (Me) OC (Me)₂C≡CH N (Me) Pr-n
CH (Me) OC (Me)₂C≡CH N (Me) Pr-i
CH (Me) OC (Me)₂C≡CH N (Me) Pr-c
CH (Me) OC (Me)₂C≡CH N (Me) Bu-n
CH (Me) OC (Me)₂C≡CH N (Me) Bu-i
CH (Me) OC (Me)₂C≡CH N (Me) Bu-c
CH (Me) OC (Me)₂C≡CH N (Me) Bu-s
CH (Me) OC (Me)₂C≡CH N (Me) Bu-t
CH (Me) OC (Me)₂C≡CH N (Me) Pen-n
CH (Me) OC (Me)₂C≡CH N (Me) Pen-c
CH (Me) OC (Me)₂C≡CH N (Me) Hex-n
CH (Me) OC (Me)₂C≡CH N (Me) Hex-c
CH (Me) OC (Me)₂C≡CH N (Me) CH₂CF_Three
C (Me)₂OCH₂C≡CH OMe
C (Me)₂OCH₂C≡CH OEt
C (Me)₂OCH₂C≡CH OPr-n
C (Me)₂OCH₂C≡CH OPr-i
C (Me)₂OCH₂C≡CH OPr-c
C (Me)₂OCH₂C≡CH OBu-n
C (Me)₂OCH₂C≡CH OBu-i
C (Me)₂OCH₂C≡CH OBu-c
C (Me)₂OCH₂C≡CH OBu-s
C (Me)₂OCH₂C≡CH OBu-t
C (Me)₂OCH₂C≡CH OPen-n
C (Me)₂OCH₂C≡CH OPen-c
C (Me)₂OCH₂C≡CH OHex-n
C (Me)₂OCH₂C≡CH OHex-c
C (Me)₂OCH₂C≡CH Me
C (Me)₂OCH₂C≡CH Et
C (Me)₂OCH₂C≡CH Pr-n
C (Me)₂OCH₂C≡CH Pr-i
C (Me)₂OCH₂C≡CH Pr-c
C (Me)₂OCH₂C≡CH Bu-n
C (Me)₂OCH₂C≡CH Bu-i
C (Me)₂OCH₂C≡CH Bu-c
C (Me)₂OCH₂C≡CH Bu-s
C (Me)₂OCH₂C≡CH Bu-t
C (Me)₂OCH₂C≡CH Pen-n
C (Me)₂OCH₂C≡CH Pen-c
C (Me)₂OCH₂C≡CH Hex-n
C (Me)₂OCH₂C≡CH Hex-c
C (Me)₂OCH₂C≡CH CH₂SMe
C (Me)₂OCH₂C≡CH CH₂S (O) Me
C (Me)₂OCH₂C≡CH CH₂S (O)₂Me
C (Me)₂OCH₂C≡CH CH₂SEt
C (Me)₂OCH₂C≡CH CH₂S (O) Et
C (Me)₂OCH₂C≡CH CH₂S (O)₂Et
C (Me)₂OCH₂C≡CH CH (Me) SMe
C (Me)₂OCH₂C≡CH CH (Me) S (O) Me
C (Me)₂OCH₂C≡CH CH (Me) S (O)₂Me
C (Me)₂OCH₂C≡CH CH (Me) SEt
C (Me)₂OCH₂C≡CH CH (Me) S (O) Et
C (Me)₂OCH₂C≡CH CH (Me) S (O)₂Et
C (Me)₂OCH₂C≡CH C (Me)₂SMe
C (Me)₂OCH₂C≡CH C (Me)₂S (O) Me
C (Me)₂OCH₂C≡CH C (Me)₂S (O)₂Me
C (Me)₂OCH₂C≡CH C (Me)₂SEt
C (Me)₂OCH₂C≡CH C (Me)₂S (O) Et
C (Me)₂OCH₂C≡CH C (Me)₂S (O)₂Et
C (Me)₂OCH₂C≡CH CH₂CH₂SMe
C (Me)₂OCH₂C≡CH CH₂CH₂S (O) Me
C (Me)₂OCH₂C≡CH CH₂CH₂S (O)₂Me
C (Me)₂OCH₂C≡CH CH (Me) CH₂SMe
C (Me)₂OCH₂C≡CH CH (Me) CH₂S (O) Me
C (Me)₂OCH₂C≡CH CH (Me) CH₂S (O)₂Me
C (Me)₂OCH₂C≡CH C (Me)₂CH₂SMe
C (Me)₂OCH₂C≡CH C (Me)₂CH₂S (O) Me
C (Me)₂OCH₂C≡CH C (Me)₂CH₂S (O)₂Me
C (Me)₂OCH₂C≡CH CH₂CH (Me) SMe
C (Me)₂OCH₂C≡CH CH₂CH (Me) S (O) Me
C (Me)₂OCH₂C≡CH CH₂CH (Me) S (O)₂Me
C (Me)₂OCH₂C≡CH CH₂C (Me)₂SMe
C (Me)₂OCH₂C≡CH CH₂C (Me)₂S (O) Me
C (Me)₂OCH₂C≡CH CH₂C (Me)₂S (O)₂Me
C (Me)₂OCH₂C≡CH CH (Me) CH (Me) SMe
C (Me)₂OCH₂C≡CH CH (Me) CH (Me) S (O) Me
C (Me)₂OCH₂C≡CH CH (Me) CH (Me) S (O)₂Me
C (Me)₂OCH₂C≡CH C (Me)₂CH (Me) SMe
C (Me)₂OCH₂C≡CH C (Me)₂CH (Me) S (O) Me
C (Me)₂OCH₂C≡CH C (Me)₂CH (Me) S (O)₂Me
C (Me)₂OCH₂C≡CH CH (Me) C (Me)₂SMe
C (Me)₂OCH₂C≡CH CH (Me) C (Me)₂S (O) Me
C (Me)₂OCH₂C≡CH CH (Me) C (Me)₂S (O)₂Me
C (Me)₂OCH₂C≡CH C (Me)₂C (Me)₂SMe
C (Me)₂OCH₂C≡CH C (Me)₂C (Me)₂S (O) Me
C (Me)₂OCH₂C≡CH C (Me)₂C (Me)₂S (O)₂Me
C (Me)₂OCH₂C≡CH CH₂CF_Three
C (Me)₂OCH₂C≡CH CH (Me) CF_Three
C (Me)₂OCH₂C≡CH CH₂CF₂CF_Three
C (Me)₂OCH₂C≡CH CH (Me) CF₂CF_Three
C (Me)₂OCH₂C≡CH CH₂CH₂CF_Three
C (Me)₂OCH₂C≡CH CH (Me) CH₂CF_Three
C (Me)₂OCH₂C≡CH CH₂CH (Me) CF_Three
C (Me)₂OCH₂C≡CH CH₂CH (CF_Three)₂
C (Me)₂OCH₂C≡CH CH (Me) CH (CF_Three)₂
C (Me)₂OCH₂C≡CH CH₂CF (CF_Three)₂
C (Me)₂OCH₂C≡CH CH (Me) CF (CF_Three)₂
C (Me)₂OCH₂C≡CH CH (CF_ThreeSMe
C (Me)₂OCH₂C≡CH CH (CF_Three) S (O) Me
C (Me)₂OCH₂C≡CH CH (CF_Three) S (O)₂Me
C (Me)₂OCH₂C≡CH CH (CF_Three) SEt
C (Me)₂OCH₂C≡CH CH (CF_Three) S (O) Et
C (Me)₂OCH₂C≡CH CH (CF_Three) S (O)₂Et
C (Me)₂OCH₂C≡CH CH (CF_Three) CH₂SMe
C (Me)₂OCH₂C≡CH CH (CF_Three) CH₂S (O) Me
C (Me)₂OCH₂C≡CH CH (CF_Three) CH₂S (O)₂Me
C (Me)₂OCH₂C≡CH CH₂CH (CF_ThreeSMe
C (Me)₂OCH₂C≡CH CH₂CH (CF_Three) S (O) Me
C (Me)₂OCH₂C≡CH CH₂CH (CF_Three) S (O)₂Me
C (Me)₂OCH₂C≡CH D1-81a
C (Me)₂OCH₂C≡CH D1-82a
C (Me)₂OCH₂C≡CH D1-84a
C (Me)₂OCH₂C≡CH D1-85a
C (Me)₂OCH₂C≡CH D1-87a
C (Me)₂OCH₂C≡CH D1-92a
C (Me)₂OCH₂C≡CH D1-93a
C (Me)₂OCH₂C≡CH D1-95a
C (Me)₂OCH₂C≡CH D1-96a
C (Me)₂OCH₂C≡CH D1-98a
C (Me)₂OCH₂C≡CH D1-103b
C (Me)₂OCH₂C≡CH D1-103e
C (Me)₂OCH₂C≡CH D1-103f
C (Me)₂OCH₂C≡CH D1-103g
C (Me)₂OCH₂C≡CH D1-103h
C (Me)₂OCH₂C≡CH D1-103i
C (Me)₂OCH₂C≡CH CH₂(D1-81a)
C (Me)₂OCH₂C≡CH CH₂(D1-82a)
C (Me)₂OCH₂C≡CH CH₂(D1-84a)
C (Me)₂OCH₂C≡CH CH₂(D1-85a)
C (Me)₂OCH₂C≡CH CH₂(D1-87a)
C (Me)₂OCH₂C≡CH CH₂(D1-92a)
C (Me)₂OCH₂C≡CH CH₂(D1-93a)
C (Me)₂OCH₂C≡CH CH₂(D1-95a)
C (Me)₂OCH₂C≡CH CH₂(D1-96a)
C (Me)₂OCH₂C≡CH CH₂(D1-98a)
C (Me)₂OCH₂C≡CH CH₂(D1-103b)
C (Me)₂OCH₂C≡CH NHMe
C (Me)₂OCH₂C≡CH NHEt
C (Me)₂OCH₂C≡CH NHPr-n
C (Me)₂OCH₂C≡CH NHPr-i
C (Me)₂OCH₂C≡CH NHPr-c
C (Me)₂OCH₂C≡CH NHBu-n
C (Me)₂OCH₂C≡CH NHBu-i
C (Me)₂OCH₂C≡CH NHBu-c
C (Me)₂OCH₂C≡CH NHBu-s
C (Me)₂OCH₂C≡CH NHBu-t
C (Me)₂OCH₂C≡CH NHPen-n
C (Me)₂OCH₂C≡CH NHPen-c
C (Me)₂OCH₂C≡CH NHHex-n
C (Me)₂OCH₂C≡CH NHHex-c
C (Me)₂OCH₂C≡CH NHCH₂CF_Three
C (Me)₂OCH₂C≡CH NMe₂
C (Me)₂OCH₂C≡CH N (Me) Et
C (Me)₂OCH₂C≡CH N (Me) Pr-n
C (Me)₂OCH₂C≡CH N (Me) Pr-i
C (Me)₂OCH₂C≡CH N (Me) Pr-c
C (Me)₂OCH₂C≡CH N (Me) Bu-n
C (Me)₂OCH₂C≡CH N (Me) Bu-i
C (Me)₂OCH₂C≡CH N (Me) Bu-c
C (Me)₂OCH₂C≡CH N (Me) Bu-s
C (Me)₂OCH₂C≡CH N (Me) Bu-t
C (Me)₂OCH₂C≡CH N (Me) Pen-n
C (Me)₂OCH₂C≡CH N (Me) Pen-c
C (Me)₂OCH₂C≡CH N (Me) Hex-n
C (Me)₂OCH₂C≡CH N (Me) Hex-c
C (Me)₂OCH₂C≡CH N (Me) CH₂CF_Three
C (Me)₂OCH (Me) C≡CH OMe
C (Me)₂OCH (Me) C≡CH OEt
C (Me)₂OCH (Me) C≡CH OPr-n
C (Me)₂OCH (Me) C≡CH OPr-i
C (Me)₂OCH (Me) C≡CH OPr-c
C (Me)₂OCH (Me) C≡CH OBu-n
C (Me)₂OCH (Me) C≡CH OBu-i
C (Me)₂OCH (Me) C≡CH OBu-c
C (Me)₂OCH (Me) C≡CH OBu-s
C (Me)₂OCH (Me) C≡CH OBu-t
C (Me)₂OCH (Me) C≡CH OPen-n
C (Me)₂OCH (Me) C≡CH OPen-c
C (Me)₂OCH (Me) C≡CH OHex-n
C (Me)₂OCH (Me) C≡CH OHex-c
C (Me)₂OCH (Me) C≡CH Me
C (Me)₂OCH (Me) C≡CH Et
C (Me)₂OCH (Me) C≡CH Pr-n
C (Me)₂OCH (Me) C≡CH Pr-i
C (Me)₂OCH (Me) C≡CH Pr-c
C (Me)₂OCH (Me) C≡CH Bu-n
C (Me)₂OCH (Me) C≡CH Bu-i
C (Me)₂OCH (Me) C≡CH Bu-c
C (Me)₂OCH (Me) C≡CH Bu-s
C (Me)₂OCH (Me) C≡CH Bu-t
C (Me)₂OCH (Me) C≡CH Pen-n
C (Me)₂OCH (Me) C≡CH Pen-c
C (Me)₂OCH (Me) C≡CH Hex-n
C (Me)₂OCH (Me) C≡CH Hex-c
C (Me)₂OCH (Me) C≡CH CH₂SMe
C (Me)₂OCH (Me) C≡CH CH₂S (O) Me
C (Me)₂OCH (Me) C≡CH CH₂S (O)₂Me
C (Me)₂OCH (Me) C≡CH CH₂SEt
C (Me)₂OCH (Me) C≡CH CH₂S (O) Et
C (Me)₂OCH (Me) C≡CH CH₂S (O)₂Et
C (Me)₂OCH (Me) C≡CH CH (Me) SMe
C (Me)₂OCH (Me) C≡CH CH (Me) S (O) Me
C (Me)₂OCH (Me) C≡CH CH (Me) S (O)₂Me
C (Me)₂OCH (Me) C≡CH CH (Me) SEt
C (Me)₂OCH (Me) C≡CH CH (Me) S (O) Et
C (Me)₂OCH (Me) C≡CH CH (Me) S (O)₂Et
C (Me)₂OCH (Me) C≡CH C (Me)₂SMe
C (Me)₂OCH (Me) C≡CH C (Me)₂S (O) Me
C (Me)₂OCH (Me) C≡CH C (Me)₂S (O)₂Me
C (Me)₂OCH (Me) C≡CH C (Me)₂SEt
C (Me)₂OCH (Me) C≡CH C (Me)₂S (O) Et
C (Me)₂OCH (Me) C≡CH C (Me)₂S (O)₂Et
C (Me)₂OCH (Me) C≡CH CH₂CH₂SMe
C (Me)₂OCH (Me) C≡CH CH₂CH₂S (O) Me
C (Me)₂OCH (Me) C≡CH CH₂CH₂S (O)₂Me
C (Me)₂OCH (Me) C≡CH CH (Me) CH₂SMe
C (Me)₂OCH (Me) C≡CH CH (Me) CH₂S (O) Me
C (Me)₂OCH (Me) C≡CH CH (Me) CH₂S (O)₂Me
C (Me)₂OCH (Me) C≡CH C (Me)₂CH₂SMe
C (Me)₂OCH (Me) C≡CH C (Me)₂CH₂S (O) Me
C (Me)₂OCH (Me) C≡CH C (Me)₂CH₂S (O)₂Me
C (Me)₂OCH (Me) C≡CH CH₂CH (Me) SMe
C (Me)₂OCH (Me) C≡CH CH₂CH (Me) S (O) Me
C (Me)₂OCH (Me) C≡CH CH₂CH (Me) S (O)₂Me
C (Me)₂OCH (Me) C≡CH CH₂C (Me)₂SMe
C (Me)₂OCH (Me) C≡CH CH₂C (Me)₂S (O) Me
C (Me)₂OCH (Me) C≡CH CH₂C (Me)₂S (O)₂Me
C (Me)₂OCH (Me) C≡CH CH (Me) CH (Me) SMe
C (Me)₂OCH (Me) C≡CH CH (Me) CH (Me) S (O) Me
C (Me)₂OCH (Me) C≡CH CH (Me) CH (Me) S (O)₂Me
C (Me)₂OCH (Me) C≡CH C (Me)₂CH (Me) SMe
C (Me)₂OCH (Me) C≡CH C (Me)₂CH (Me) S (O) Me
C (Me)₂OCH (Me) C≡CH C (Me)₂CH (Me) S (O)₂Me
C (Me)₂OCH (Me) C≡CH CH (Me) C (Me)₂SMe
C (Me)₂OCH (Me) C≡CH CH (Me) C (Me)₂S (O) Me
C (Me)₂OCH (Me) C≡CH CH (Me) C (Me)₂S (O)₂Me
C (Me)₂OCH (Me) C≡CH C (Me)₂C (Me)₂SMe
C (Me)₂OCH (Me) C≡CH C (Me)₂C (Me)₂S (O) Me
C (Me)₂OCH (Me) C≡CH C (Me)₂C (Me)₂S (O)₂Me
C (Me)₂OCH (Me) C≡CH CH₂CF_Three
C (Me)₂OCH (Me) C≡CH CH (Me) CF_Three
C (Me)₂OCH (Me) C≡CH CH₂CF₂CF_Three
C (Me)₂OCH (Me) C≡CH CH (Me) CF₂CF_Three
C (Me)₂OCH (Me) C≡CH CH₂CH₂CF_Three
C (Me)₂OCH (Me) C≡CH CH (Me) CH₂CF_Three
C (Me)₂OCH (Me) C≡CH CH₂CH (Me) CF_Three
C (Me)₂OCH (Me) C≡CH CH₂CH (CF_Three)₂
C (Me)₂OCH (Me) C≡CH CH (Me) CH (CF_Three)₂
C (Me)₂OCH (Me) C≡CH CH₂CF (CF_Three)₂
C (Me)₂OCH (Me) C≡CH CH (Me) CF (CF_Three)₂
C (Me)₂OCH (Me) C≡CH CH (CF_ThreeSMe
C (Me)₂OCH (Me) C≡CH CH (CF_Three) S (O) Me
C (Me)₂OCH (Me) C≡CH CH (CF_Three) S (O)₂Me
C (Me)₂OCH (Me) C≡CH CH (CF_Three) SEt
C (Me)₂OCH (Me) C≡CH CH (CF_Three) S (O) Et
C (Me)₂OCH (Me) C≡CH CH (CF_Three) S (O)₂Et
C (Me)₂OCH (Me) C≡CH CH (CF_Three) CH₂SMe
C (Me)₂OCH (Me) C≡CH CH (CF_Three) CH₂S (O) Me
C (Me)₂OCH (Me) C≡CH CH (CF_Three) CH₂S (O)₂Me
C (Me)₂OCH (Me) C≡CH CH₂CH (CF_ThreeSMe
C (Me)₂OCH (Me) C≡CH CH₂CH (CF_Three) S (O) Me
C (Me)₂OCH (Me) C≡CH CH₂CH (CF_Three) S (O)₂Me
C (Me)₂OCH (Me) C≡CH D1-81a
C (Me)₂OCH (Me) C≡CH D1-82a
C (Me)₂OCH (Me) C≡CH D1-84a
C (Me)₂OCH (Me) C≡CH D1-85a
C (Me)₂OCH (Me) C≡CH D1-87a
C (Me)₂OCH (Me) C≡CH D1-92a
C (Me)₂OCH (Me) C≡CH D1-93a
C (Me)₂OCH (Me) C≡CH D1-95a
C (Me)₂OCH (Me) C≡CH D1-96a
C (Me)₂OCH (Me) C≡CH D1-98a
C (Me)₂OCH (Me) C≡CH D1-103b
C (Me)₂OCH (Me) C≡CH D1-103e
C (Me)₂OCH (Me) C≡CH D1-103f
C (Me)₂OCH (Me) C≡CH D1-103g
C (Me)₂OCH (Me) C≡CH D1-103h
C (Me)₂OCH (Me) C≡CH D1-103i
C (Me)₂OCH (Me) C≡CH CH₂(D1-81a)
C (Me)₂OCH (Me) C≡CH CH₂(D1-82a)
C (Me)₂OCH (Me) C≡CH CH₂(D1-84a)
C (Me)₂OCH (Me) C≡CH CH₂(D1-85a)
C (Me)₂OCH (Me) C≡CH CH₂(D1-87a)
C (Me)₂OCH (Me) C≡CH CH₂(D1-92a)
C (Me)₂OCH (Me) C≡CH CH₂(D1-93a)
C (Me)₂OCH (Me) C≡CH CH₂(D1-95a)
C (Me)₂OCH (Me) C≡CH CH₂(D1-96a)
C (Me)₂OCH (Me) C≡CH CH₂(D1-98a)
C (Me)₂OCH (Me) C≡CH CH₂(D1-103b)
C (Me)₂OCH (Me) C≡CH NHMe
C (Me)₂OCH (Me) C≡CH NHEt
C (Me)₂OCH (Me) C≡CH NHPr-n
C (Me)₂OCH (Me) C≡CH NHPr-i
C (Me)₂OCH (Me) C≡CH NHPr-c
C (Me)₂OCH (Me) C≡CH NHBu-n
C (Me)₂OCH (Me) C≡CH NHBu-i
C (Me)₂OCH (Me) C≡CH NHBu-c
C (Me)₂OCH (Me) C≡CH NHBu-s
C (Me)₂OCH (Me) C≡CH NHBu-t
C (Me)₂OCH (Me) C≡CH NHPen-n
C (Me)₂OCH (Me) C≡CH NHPen-c
C (Me)₂OCH (Me) C≡CH NHHex-n
C (Me)₂OCH (Me) C≡CH NHHex-c
C (Me)₂OCH (Me) C≡CH NHCH₂CF_Three
C (Me)₂OCH (Me) C≡CH NMe₂
C (Me)₂OCH (Me) C≡CH N (Me) Et
C (Me)₂OCH (Me) C≡CH N (Me) Pr-n
C (Me)₂OCH (Me) C≡CH N (Me) Pr-i
C (Me)₂OCH (Me) C≡CH N (Me) Pr-c
C (Me)₂OCH (Me) C≡CH N (Me) Bu-n
C (Me)₂OCH (Me) C≡CH N (Me) Bu-i
C (Me)₂OCH (Me) C≡CH N (Me) Bu-c
C (Me)₂OCH (Me) C≡CH N (Me) Bu-s
C (Me)₂OCH (Me) C≡CH N (Me) Bu-t
C (Me)₂OCH (Me) C≡CH N (Me) Pen-n
C (Me)₂OCH (Me) C≡CH N (Me) Pen-c
C (Me)₂OCH (Me) C≡CH N (Me) Hex-n
C (Me)₂OCH (Me) C≡CH N (Me) Hex-c
C (Me)₂OCH (Me) C≡CH N (Me) CH₂CF_Three
C (Me)₂OC (Me)₂C≡CH OMe
C (Me)₂OC (Me)₂C≡CH OEt
C (Me)₂OC (Me)₂C≡CH OPr-n
C (Me)₂OC (Me)₂C≡CH OPr-i
C (Me)₂OC (Me)₂C≡CH OPr-c
C (Me)₂OC (Me)₂C≡CH OBu-n
C (Me)₂OC (Me)₂C≡CH OBu-i
C (Me)₂OC (Me)₂C≡CH OBu-c
C (Me)₂OC (Me)₂C≡CH OBu-s
C (Me)₂OC (Me)₂C≡CH OBu-t
C (Me)₂OC (Me)₂C≡CH OPen-n
C (Me)₂OC (Me)₂C≡CH OPen-c
C (Me)₂OC (Me)₂C≡CH OHex-n
C (Me)₂OC (Me)₂C≡CH OHex-c
C (Me)₂OC (Me)₂C≡CH Me
C (Me)₂OC (Me)₂C≡CH Et
C (Me)₂OC (Me)₂C≡CH Pr-n
C (Me)₂OC (Me)₂C≡CH Pr-i
C (Me)₂OC (Me)₂C≡CH Pr-c
C (Me)₂OC (Me)₂C≡CH Bu-n
C (Me)₂OC (Me)₂C≡CH Bu-i
C (Me)₂OC (Me)₂C≡CH Bu-c
C (Me)₂OC (Me)₂C≡CH Bu-s
C (Me)₂OC (Me)₂C≡CH Bu-t
C (Me)₂OC (Me)₂C≡CH Pen-n
C (Me)₂OC (Me)₂C≡CH Pen-c
C (Me)₂OC (Me)₂C≡CH Hex-n
C (Me)₂OC (Me)₂C≡CH Hex-c
C (Me)₂OC (Me)₂C≡CH CH₂SMe
C (Me)₂OC (Me)₂C≡CH CH₂S (O) Me
C (Me)₂OC (Me)₂C≡CH CH₂S (O)₂Me
C (Me)₂OC (Me)₂C≡CH CH₂SEt
C (Me)₂OC (Me)₂C≡CH CH₂S (O) Et
C (Me)₂OC (Me)₂C≡CH CH₂S (O)₂Et
C (Me)₂OC (Me)₂C≡CH CH (Me) SMe
C (Me)₂OC (Me)₂C≡CH CH (Me) S (O) Me
C (Me)₂OC (Me)₂C≡CH CH (Me) S (O)₂Me
C (Me)₂OC (Me)₂C≡CH CH (Me) SEt
C (Me)₂OC (Me)₂C≡CH CH (Me) S (O) Et
C (Me)₂OC (Me)₂C≡CH CH (Me) S (O)₂Et
C (Me)₂OC (Me)₂C≡CH C (Me)₂SMe
C (Me)₂OC (Me)₂C≡CH C (Me)₂S (O) Me
C (Me)₂OC (Me)₂C≡CH C (Me)₂S (O)₂Me
C (Me)₂OC (Me)₂C≡CH C (Me)₂SEt
C (Me)₂OC (Me)₂C≡CH C (Me)₂S (O) Et
C (Me)₂OC (Me)₂C≡CH C (Me)₂S (O)₂Et
C (Me)₂OC (Me)₂C≡CH CH₂CH₂SMe
C (Me)₂OC (Me)₂C≡CH CH₂CH₂S (O) Me
C (Me)₂OC (Me)₂C≡CH CH₂CH₂S (O)₂Me
C (Me)₂OC (Me)₂C≡CH CH (Me) CH₂SMe
C (Me)₂OC (Me)₂C≡CH CH (Me) CH₂S (O) Me
C (Me)₂OC (Me)₂C≡CH CH (Me) CH₂S (O)₂Me
C (Me)₂OC (Me)₂C≡CH C (Me)₂CH₂SMe
C (Me)₂OC (Me)₂C≡CH C (Me)₂CH₂S (O) Me
C (Me)₂OC (Me)₂C≡CH C (Me)₂CH₂S (O)₂Me
C (Me)₂OC (Me)₂C≡CH CH₂CH (Me) SMe
C (Me)₂OC (Me)₂C≡CH CH₂CH (Me) S (O) Me
C (Me)₂OC (Me)₂C≡CH CH₂CH (Me) S (O)₂Me
C (Me)₂OC (Me)₂C≡CH CH₂C (Me)₂SMe
C (Me)₂OC (Me)₂C≡CH CH₂C (Me)₂S (O) Me
C (Me)₂OC (Me)₂C≡CH CH₂C (Me)₂S (O)₂Me
C (Me)₂OC (Me)₂C≡CH CH (Me) CH (Me) SMe
C (Me)₂OC (Me)₂C≡CH CH (Me) CH (Me) S (O) Me
C (Me)₂OC (Me)₂C≡CH CH (Me) CH (Me) S (O)₂Me
C (Me)₂OC (Me)₂C≡CH C (Me)₂CH (Me) SMe
C (Me)₂OC (Me)₂C≡CH C (Me)₂CH (Me) S (O) Me
C (Me)₂OC (Me)₂C≡CH C (Me)₂CH (Me) S (O)₂Me
C (Me)₂OC (Me)₂C≡CH CH (Me) C (Me)₂SMe
C (Me)₂OC (Me)₂C≡CH CH (Me) C (Me)₂S (O) Me
C (Me)₂OC (Me)₂C≡CH CH (Me) C (Me)₂S (O)₂Me
C (Me)₂OC (Me)₂C≡CH C (Me)₂C (Me)₂SMe
C (Me)₂OC (Me)₂C≡CH C (Me)₂C (Me)₂S (O) Me
C (Me)₂OC (Me)₂C≡CH C (Me)₂C (Me)₂S (O)₂Me
C (Me)₂OC (Me)₂C≡CH CH₂CF_Three
C (Me)₂OC (Me)₂C≡CH CH (Me) CF_Three
C (Me)₂OC (Me)₂C≡CH CH₂CF₂CF_Three
C (Me)₂OC (Me)₂C≡CH CH (Me) CF₂CF_Three
C (Me)₂OC (Me)₂C≡CH CH₂CH₂CF_Three
C (Me)₂OC (Me)₂C≡CH CH (Me) CH₂CF_Three
C (Me)₂OC (Me)₂C≡CH CH₂CH (Me) CF_Three
C (Me)₂OC (Me)₂C≡CH CH₂CH (CF_Three)₂
C (Me)₂OC (Me)₂C≡CH CH (Me) CH (CF_Three)₂
C (Me)₂OC (Me)₂C≡CH CH₂CF (CF_Three)₂
C (Me)₂OC (Me)₂C≡CH CH (Me) CF (CF_Three)₂
C (Me)₂OC (Me)₂C≡CH CH (CF_ThreeSMe
C (Me)₂OC (Me)₂C≡CH CH (CF_Three) S (O) Me
C (Me)₂OC (Me)₂C≡CH CH (CF_Three) S (O)₂Me
C (Me)₂OC (Me)₂C≡CH CH (CF_Three) SEt
C (Me)₂OC (Me)₂C≡CH CH (CF_Three) S (O) Et
C (Me)₂OC (Me)₂C≡CH CH (CF_Three) S (O)₂Et
C (Me)₂OC (Me)₂C≡CH CH (CF_Three) CH₂SMe
C (Me)₂OC (Me)₂C≡CH CH (CF_Three) CH₂S (O) Me
C (Me)₂OC (Me)₂C≡CH CH (CF_Three) CH₂S (O)₂Me
C (Me)₂OC (Me)₂C≡CH CH₂CH (CF_ThreeSMe
C (Me)₂OC (Me)₂C≡CH CH₂CH (CF_Three) S (O) Me
C (Me)₂OC (Me)₂C≡CH CH₂CH (CF_Three) S (O)₂Me
C (Me)₂OC (Me)₂C≡CH D1-81a
C (Me)₂OC (Me)₂C≡CH D1-82a
C (Me)₂OC (Me)₂C≡CH D1-84a
C (Me)₂OC (Me)₂C≡CH D1-85a
C (Me)₂OC (Me)₂C≡CH D1-87a
C (Me)₂OC (Me)₂C≡CH D1-92a
C (Me)₂OC (Me)₂C≡CH D1-93a
C (Me)₂OC (Me)₂C≡CH D1-95a
C (Me)₂OC (Me)₂C≡CH D1-96a
C (Me)₂OC (Me)₂C≡CH D1-98a
C (Me)₂OC (Me)₂C≡CH D1-103b
C (Me)₂OC (Me)₂C≡CH D1-103e
C (Me)₂OC (Me)₂C≡CH D1-103f
C (Me)₂OC (Me)₂C≡CH D1-103g
C (Me)₂OC (Me)₂C≡CH D1-103h
C (Me)₂OC (Me)₂C≡CH D1-103i
C (Me)₂OC (Me)₂C≡CH CH₂(D1-81a)
C (Me)₂OC (Me)₂C≡CH CH₂(D1-82a)
C (Me)₂OC (Me)₂C≡CH CH₂(D1-84a)
C (Me)₂OC (Me)₂C≡CH CH₂(D1-85a)
C (Me)₂OC (Me)₂C≡CH CH₂(D1-87a)
C (Me)₂OC (Me)₂C≡CH CH₂(D1-92a)
C (Me)₂OC (Me)₂C≡CH CH₂(D1-93a)
C (Me)₂OC (Me)₂C≡CH CH₂(D1-95a)
C (Me)₂OC (Me)₂C≡CH CH₂(D1-96a)
C (Me)₂OC (Me)₂C≡CH CH₂(D1-98a)
C (Me)₂OC (Me)₂C≡CH CH₂(D1-103b)
C (Me)₂OC (Me)₂C≡CH NHMe
C (Me)₂OC (Me)₂C≡CH NHEt
C (Me)₂OC (Me)₂C≡CH NHPr-n
C (Me)₂OC (Me)₂C≡CH NHPr-i
C (Me)₂OC (Me)₂C≡CH NHPr-c
C (Me)₂OC (Me)₂C≡CH NHBu-n
C (Me)₂OC (Me)₂C≡CH NHBu-i
C (Me)₂OC (Me)₂C≡CH NHBu-c
C (Me)₂OC (Me)₂C≡CH NHBu-s
C (Me)₂OC (Me)₂C≡CH NHBu-t
C (Me)₂OC (Me)₂C≡CH NHPen-n
C (Me)₂OC (Me)₂C≡CH NHPen-c
C (Me)₂OC (Me)₂C≡CH NHHex-n
C (Me)₂OC (Me)₂C≡CH NHHex-c
C (Me)₂OC (Me)₂C≡CH NHCH₂CF_Three
C (Me)₂OC (Me)₂C≡CH NMe₂
C (Me)₂OC (Me)₂C≡CH N (Me) Et
C (Me)₂OC (Me)₂C≡CH N (Me) Pr-n
C (Me)₂OC (Me)₂C≡CH N (Me) Pr-i
C (Me)₂OC (Me)₂C≡CH N (Me) Pr-c
C (Me)₂OC (Me)₂C≡CH N (Me) Bu-n
C (Me)₂OC (Me)₂C≡CH N (Me) Bu-i
C (Me)₂OC (Me)₂C≡CH N (Me) Bu-c
C (Me)₂OC (Me)₂C≡CH N (Me) Bu-s
C (Me)₂OC (Me)₂C≡CH N (Me) Bu-t
C (Me)₂OC (Me)₂C≡CH N (Me) Pen-n
C (Me)₂OC (Me)₂C≡CH N (Me) Pen-c
C (Me)₂OC (Me)₂C≡CH N (Me) Hex-n
C (Me)₂OC (Me)₂C≡CH N (Me) Hex-c
C (Me)₂OC (Me)₂C≡CH N (Me) CH₂CF_Three
―――――――――――――――――――――――
  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, mollusks and nematodes that can be controlled using the compounds of the present invention include, for example, the wasp chestnut gall wasp (Dryocosmus kuriphilus), the Argentine ant Argentine ant (Linepithema humile), Gunmy ant Army ant (Eciton burchelli, E. schmitti), Japanese carpenter ant (Camponotus japonicus), Green ant Pharaoh ant (Monomorium pharaonis), Bulldog ant class Bulldog ant (Myrmecia spp.), Fire ant class fire spant (Soop) , Asian giant hornet (Vespa mandarina), Japanese yellow hornet (Vespa simillima), large bee Large rose sawfly (Arge pagana), pine bee European pine sawfly (Neodiprion sertifer), bb sawfly (Athalia infumata), turnip sawnip (Turnip sawfly) Hymenoptera insects such as 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), etc. Piroplasmida sporophytes,
Haemoproteus mansoni, chicken leucocytozone (Leucocytozoon caulleryi), Plasmodium falciparum, Plasmodium malariae, Plasmodium ovale, Plasmodium ovale Haemosporida spores such as Plasmodium vivax,
Caryospora spp., Eimeria acervulina, Eimeria bovis, Eimeria brunetti, Eimeria maxima, Eimeria necatrix, Eimeria necatrix Eimeria ovinoidalis, rabbit liver coccidium (Eimeria stiedae), chicken cecal coccidium (Eimeria tenella), dog isospora canis, feline isospora (Isospora felis), porcine isospora suis (Isospora suis), Tizeria aleni , Tyzzeria anseris, Tyzzeria perniciosa, Wenyonella anatis, Wenyonella gagari, Cryptosporidium canis, cat crypt Cryptosporidium felis, Cryptosporidium hominis, turkey Cryptosporidium meleagridis, Cryptosporidium muris, small Cryptosporidium parvco, sarcosis (Sarcocystis cruzi), Sarcocystis felis, Sarcocystis hominis, Sarcocystis miescheriana, Sarcocystis neurona, Sarcocystis colostis tenis S tenis Sarcocystis ovalis), Toxoplasma gondii, dog hepatozoon (Hepatozoon canis), cat hepatozoon (Hepatozoon felis), etc. cidiorida) spores,
Vestibuliferida ciliates, such as large intestine barantidium coli,
Histomanas meleagridis, Pentatrichomonas hominis, Trichomonas tenax and other Trichomonadida flagellates,
Dipromonads (Diplomonadida) flagellates such as Giardia intestinalis, Giardia muris, turkey hexamita (Hexamita meleagridis), Hexamita parva,
Leishmania donovani, Leishmania infantum, Leishmania major, Leishmania tropica, Trypanosoma brucei gambiense, Trypanosoma brucei cruise, Trypanosoma brucei rhodesi Examples include Trypanosoma cruzi, Trypanosoma equiperdum, Trypanosoma evansi, and Kinetoplastida flagellates, which can be controlled using the compounds of the present invention. Pests and ectoparasites such as livestock, poultry and pets 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 (Coleoptera); 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-butylyl 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 0.1-80 parts Solid carrier 5-98.9 parts Surfactant 1-10 parts Others 0-5 parts Others include, for example, anti-caking agents and decomposition inhibitors.

〔emulsion〕
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 and decomposition inhibitors.

[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] Granule Compound No. 1-001 of the present invention 5 parts Bentonite 50 parts Talc 45 parts After uniformly mixing and pulverizing the above, a small amount of water is added and mixed with stirring, and granulated with an extrusion granulator. And dried into granules.

[Formulation 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 azide), potassium hydrogen carbonate (potassium hydrogen carbonate), proquinazid (proquinazid) (proquinazid (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 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 tert-butyl prop-2-ynyl {2- (pyridin-3-yl) thiazol-5-yl} carbamate (present compound 1-001)
tert-Butyl {2- (pyridin-3-yl) thiazol-5-yl} carbamate 2.0 g in 20 ml N, N-dimethylformamide solution at 0 ° C. 60 wt% sodium hydride (dispersed in mineral oil) 0.35 g was added. After completion of the addition, the reaction mixture was stirred at the same temperature for 15 minutes. After the completion of stirring, 0.94 g of propargyl bromide was added dropwise to the reaction mixture at 0 ° C. After completion of dropping, stirring was continued for 3 hours at room temperature. After completion of the reaction, 30 ml of water was added to the reaction mixture and extracted with 50 ml of ethyl acetate. The obtained organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was subjected to medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate {10: 1 to 1: 1 (volume ratio, the same shall apply hereinafter)}. Purification gave 1.5 g of the desired product as a pale yellow solid.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 9.10 (d, J = 1.8 Hz, 1H), 8.68 (dd, J = 4.8, 1.5 Hz, 1H), 8.20 −8.15 (m, 1H), 7.61 (s, 1H), 7.35 (dd, J = 7.5, 4.8 Hz, 1H), 4.55 (d, J = 2.4 Hz, 2H), 2.35 (t, J = 2.4 Hz, 1H), 1.57 (s, 9H)
Melting point 102-104 ° C
Synthesis example 2
Production of tert-butyl {4-chloro-2- (pyridin-3-yl) thiazol-5-yl} (prop-2-yn-1-yl) carbamate (present compound 1-002)
To a solution of 1.4 g of tert-butyl prop-2-ynyl {2- (pyridin-3-yl) thiazol-5-yl} carbamate in 20 ml of acetonitrile was added 1.2 g of N-chlorosuccinimide. After completion of the addition, the mixture was stirred at 50 ° C. for 2 hours, and further stirred at room temperature for 15 hours. After completion of the reaction, the solvent was distilled off from the reaction mixture under reduced pressure. 30 ml of water was added to the obtained residue, and extracted with 30 ml of chloroform. The obtained organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (10: 1 to 1: 1). 7 g was obtained as a light brown solid.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 9.10 (d, J = 1.8 Hz, 1H), 8.68 (dd, J = 4.8, 1.5 Hz, 1H), 8.25 −8.15 (m, 1H), 7.40 (dd, J = 7.8, 4.8 Hz, 1H), 4.43 (d, J = 2.4 Hz, 2H), 2.33 (t, J = 2.4Hz, 1H), 1.58 (s, 9H)
Melting point 63-65 ° C
Synthesis example 3
Production of N- (4-chloro-2- (pyridin-3-yl) thiazol-5-yl) -3- (methylthio) -N- (prop-2-yn-1-yl) propanamide (the compound of the present invention) 1-003)
Process 1
Preparation of 4-chloro-N- (prop-2-yn-1-yl) -2- (pyridin-3-yl) thiazol-5-amine tert-butyl {4-chloro-2- (pyridin-3-yl) ) To a solution of thiazol-5-yl} (prop-2-yn-1-yl) carbamate in 200 mg of 1,4-dioxane in 1 ml was added 3 ml of a 1,4-dioxane solution of hydrogen chloride (about 4M). After completion of the addition, the mixture was stirred at room temperature for 5 hours. After completion of the reaction, the solvent was distilled off from the reaction mixture under reduced pressure. After adding 4 ml of methylene chloride to the obtained residue, a saturated aqueous sodium hydrogen carbonate solution was added until the pH reached 9. After the addition was complete, the reaction mixture was stirred at room temperature for 30 minutes. After completion of the reaction, 10 ml of water was added to the reaction mixture and extracted with chloroform (5 ml × 3). The obtained organic layer was washed and dried in the order of saturated brine and then anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 114 mg of the desired product as a brown solid.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 9.00 (d, J = 2.4 Hz, 1H), 8.57 (dd, J = 4.8, 1.8 Hz, 1H), 8.10 (Ddd, J = 7.8, 2.4, 1.8 Hz, 1H), 7.33 (dd, J = 7.8, 4.8 Hz, 1H), 4.24-4.14 (m, 1H ), 4.00 (dd, J = 6.0, 2.4 Hz, 2H), 2.36 (t, J = 2.4 Hz, 1H)
Melting point: 148-149 ° C
Process 2
Preparation of N- {4-chloro-2- (pyridin-3-yl) thiazol-5-yl} -3- (methylthio) -N- (prop-2-yn-1-yl) propanamide 4-Chloro- To a solution of 103 mg of N- (prop-2-yn-1-yl) -2- (pyridin-3-yl) thiazol-5-amine in 3 ml of methylene chloride was added 40 mg of pyridine, 70 mg of 3- (methylthio) propionyl chloride and 4- 5 mg of dimethylaminopyridine was added sequentially. After the addition was complete, the mixture was stirred overnight at room temperature. After the stirring, 35 mg of 3- (methylthio) propionyl chloride was added to the reaction mixture, and the reaction was continued at the same temperature for 2 hours. After completion of the reaction, 15 ml of water was added to the reaction mixture and extracted with chloroform (10 ml × 3). The obtained organic layer was washed and dried in the order of saturated brine and then anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (9: 1 to 1: 1) to obtain 44 mg of the objective product as a yellow oil.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 9.14 (d, J = 1.5 Hz, 1H), 8.73 (dd, J = 4.8, 1.5 Hz, 1H), 8.28 -8.21 (m, 1H), 7.44 (dd, J = 8.1, 4.8 Hz, 1H), 5.10-4.60 (m, 1H), 4.50-3.90 ( m, 1H), 2.82 (t, J = 7.2 Hz, 2H), 2.65-2.50 (m, 2H), 2.35-2.30 (m, 1H), 2.08 ( s, 3H)
Synthesis example 4
(S) -N- {4-Chloro-2- (pyridin-3-yl) thiazol-5-yl} -2-methyl-3- (methylthio) -N- (prop-2-yn-1-yl) Production of Propanamide To a solution of 0.97 g of (S) -2-methyl-3- (methylthio) propanoic acid synthesized according to the method described in US Patent Application Publication No. 2005/146823, 10 ml of dichloromethane was added oxalyl chloride. 92 g and then 20 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, and the resulting residue was separately prepared 4-chloro-N- (prop-2-yn-1-yl) -2- (pyridin-3-yl). ) 0.62 g of thiazol-5-amine, 0.24 g of triethylamine and 0.73 g of 4-dimethylaminopyridine were added to a 14 ml solution of 1,2-dichloroethane, and the mixture was stirred at 65 ° C. for 2 hours. After completion of the reaction, 10 ml of water was added to the reaction solution and extracted with 15 ml of chloroform. 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 (5: 1 to 1: 2) to obtain 0.93 g of the objective material as a pale yellow solid.
Melting point: 87-92 ° C
Specific rotation: [α] _D ^23.7 -7.28 ° (CHCl ₃ , c = 0.103)
[Reference example]
Synthesis of tert-butyl {2- (pyridin-3-yl) thiazol-5-yl} carbamate To a solution of 8.0 g of 2- (pyridin-3-yl) thiazole-5-carboxylic acid in 90 ml of toluene, 2-methyl- 30 ml of 2-propanol, 9.8 g of triethylamine and 16.0 g of diphenylphosphoryl azide were sequentially added. After completion of the addition, the reaction mixture was heated to 100 ° C. and stirred at the same temperature for 2.5 hours. After completion of the reaction, 150 ml of water was added and extracted with 150 ml of ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by column chromatography eluting with ethyl acetate. The obtained solid was washed with diisopropyl ether to obtain 6.6 g of the desired product as a light brown solid.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 9.10 (d, J = 1.8 Hz, 1H), 8.59 (dd, J = 4.8, 1.5 Hz, 1H), 8.15 (Dt, J = 8.1, 2.1 Hz, 1H), 7.50-7.40 (m, 2H), 7.35 (ddd, J = 7.8, 4.8, 0.6 Hz, 1H ), 1.55 (s, 9H)
This invention compound can be manufactured according to the said manufacturing method and an Example. Examples of the compounds of the present invention produced in the same manner as in Synthesis Examples 1 to 4 are shown in Tables 2 and 3, and their physical properties are shown in Table 4. However, the present invention is not limited to these. .

  * 1 represents a resinous state. * 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 4. “M.p.” represents a melting point. “Decomp.” Represents decomposition.

The symbols in Table 4 have the following meanings.
s: singlet, d: doublet, t: triplet, q: quartet, qui: quintet, sxt: sickted, sep: septette, m: multiplet, brs: broad peak.

[Table 2]

―――――――――――――――――――――――――――――――――――――
No. R ³ YR ^a R ^b-1 mp (℃)
―――――――――――――――――――――――――――――――――――――
1-001 HO CH ₂ C≡CH OC (CH ₃ ) ₃ 102-104
1-002 Cl O CH ₂ C≡CH OC (CH ₃ ) ₃ 63-65
1-003 Cl O CH ₂ C≡CH CH ₂ CH ₂ SCH ₃ * 1
1-004 Me O CH ₂ C≡CH OC (CH ₃ ) ₃ * 1
1-005 Cl O CH ₂ C≡CH CH (CH ₃ ) CH ₂ S (O) ₂ CH ₃ * 1
1-006 Me O CH ₂ C≡CH CH (CH ₃ ) SCH ₃ 36-38
1-007 Me O CH ₂ C≡CH CH (CH ₃ ) S (O) CH ₃ 38-40
1-008 Me O CH ₂ C≡CH CH (CH ₃ ) S (O) ₂ CH ₃ 140-142
1-009 Me O CH ₂ C≡CH CH (CH ₃ ) S (O) CH ₂ CH ₃ 60-62
1-010 Me O CH ₂ C≡CH CH (CH ₃ ) S (O) ₂ CH ₂ CH ₃ 146-148
1-011 Me O CH ₂ C≡CH CH (CF ₃ ) CH ₂ SCH ₃ * 2 (~ 3: 2)
1-012 Me O CH ₂ C≡CH CH ₂ CH (CF ₃ ) SCH ₃ 77-79
1-013 Me O CH ₂ C≡CH CH = CH (CF ₃ ) 39-41
1-014 Me O CH ₂ C≡CH CH ₂ CH (CF ₃ ) S (O) ₂ CH ₃ 94-96
1-015 Me O CH ₂ C≡CH CH (CH ₃ ) ₂ 64-67
1-016 Cl O CH ₂ C≡CH CH (CH ₃ ) ₂ 67-69
1-017 Me O CH ₂ C≡CH CH (CH ₃ ) CH ₂ CF ₃ 220 (decomp.)
1-018 Me O CH ₂ C≡CH NHCH ₂ CF ₃ 169-172
1-019 Me O CH ₂ C≡CH N (CH ₃ ) CH ₂ CF ₃ * 1
1-020 Cl O CH ₂ C≡CH NHCH ₂ CF ₃ 170-172
1-021 Cl O CH ₂ C≡CH N (CH ₃ ) CH ₂ CF ₃ * 1
1-022 Me O CH ₂ C≡CH CH (CH ₃ ) SCH ₂ CH ₃ * 1
1-023 Cl O CH ₂ C≡CH CH (CH ₃ ) SCH ₃ * 1
1-024 Cl O CH ₂ C≡CH CH (CH ₃ ) S (O) CH ₃ 50-54
1-025 Cl O CH ₂ C≡CH CH (CH ₃ ) S (O) ₂ CH ₃ 138-140
1-026 Cl O CH ₂ C≡CH CH (CH ₃ ) SCH ₂ CH ₃ * 1
1-027 Cl O CH ₂ C≡CH CH (CH ₃ ) S (O) CH ₂ CH ₃ * 2 (~ 9: 1)
1-028 Cl O CH ₂ C≡CH CH (CH ₃ ) S (O) ₂ CH ₂ CH ₃ 128-130
1-029 Me O CH ₂ C≡CH CH (CF ₃ ) CH ₂ S (O) CH ₃ 55-60
1-030 Me O CH ₂ C≡CH CH (CF ₃ ) CH ₂ S (O) ₂ CH ₃ 55-65
1-031 Cl O CH ₂ C≡CH CH (CF ₃ ) CH ₂ SCH ₃ 80-87
1-032 Cl O CH ₂ C≡CH CH (CF ₃ ) CH ₂ S (O) CH ₃ * 2 (~ 9: 1)
1-033 Cl O CH ₂ C≡CH CH (CF ₃ ) CH ₂ S (O) ₂ CH ₃ 130-133
1-034 Cl O CH ₂ C≡CH CH ₂ CH (CF ₃ ) SCH ₃ 88-93
1-035 Cl O CH ₂ C≡CH CH ₂ CH (CF ₃ ) S (O) ₂ CH ₃ 119-121
1-036 Me O CH ₂ C≡CH D1-103g * 1
1-037 Me O CH ₂ C≡CH D1-103h 65-75
1-038 Me O CH ₂ C≡CH D1-103i * 1
1-039 Cl O CH ₂ C≡CH D1-103g * 1
1-040 Cl O CH ₂ C≡CH D1-103h * 2 (~ 1: 1)
1-041 Cl O CH ₂ C≡CH D1-103i * 1
1-042 Cl O CH ₂ C≡CH CH (CH ₃ ) CH ₂ CF ₃ * 1
―――――――――――――――――――――――――――――――――――――
[Table 3]

―――――――――――――――――――――――――――――――――――――
No. R ³ YR ^a R ^b-2 Melting point (℃)
Absolute configuration Specific rotation ――――――――――――――――――――――――――――――――――――――
2-001 Cl O CH ₂ C≡CH CH (CH ₃ ) CH ₂ SCH ₃ 87-92
(S)-(-) [α] _D ^23.7 -7.28 ° (CHCl ₃ , c = 0.103)
2-002 Cl O CH ₂ C≡CH CH (CH ₃ ) CH ₂ S (O) CH ₃ * 1
(S)-(+) [α] _D ^22.8 + 9.84 ° (CHCl ₃ , c = 0.379)
―――――――――――――――――――――――――――――――――――――
[Table 4]
―――――――――――――――――――――――――――――――――――――――
No.
Proton nuclear magnetic resonance chemical shift value (in CDCl ₃ ): σ (ppm)
―――――――――――――――――――――――――――――――――――――――
1-003;
9.14 (d, J = 1.5 Hz, 1H), 8.73 (dd, J = 4.8, 1.5 Hz, 1H), 8.28-8.21 (m, 1H), 7.44 (Dd, J = 8.1, 4.8 Hz, 1H), 5.10-4.60 (m, 1H), 4.50-3.90 (m, 1H), 2.82 (t, J = 7.2 Hz, 2H), 2.65-2.50 (m, 2H), 2.35-2.30 (m, 1H), 2.08 (s, 3H)
1-004;
9.09 (d, J = 2.4 Hz, 1H), 8.63 (dd, J = 4.8, 1.8 Hz, 1H), 8.18 (ddd, J = 7.8, 2.4) 1.8 Hz, 1H), 7.36 (dd, J = 7.8, 4.8 Hz, 1H), 4.35 (d, J = 2.4 Hz, 2H), 2.36 (s, 3H), 2.31 (t, J = 2.4 Hz, 1H), 1.45 (s, 9H)
1-005;
9.20-9.10 (m, 1H), 8.73 (d, J = 4.8 Hz, 1H), 8.28-8.18 (m, 1H), 7.42 (dd, J = 7 .5, 4.8 Hz, 1H), 4.99 (d, J = 16.5 Hz, 1H), 4.20-4.00 (m, 1H), 3.90-3.70 (m, 1H) 3.38-3.22 (m, 1H), 3.02-2.96 (m, 1H), 2.94 (s, 3H), 2.34 (t, J = 2.7 Hz, 1H) 1.31 (d, J = 6.9 Hz, 3H)
1-011;
(Isomer ratio 3) 9.20-9.10 (m, 1H), 8.75-8.65 (m, 1H), 8.27-8.17 (m, 1H), 7.45-7 .35 (m, 1H), 4.83-4.70 (m, 1H), 4.43-4.27 (m, 1H), 3.70-3.55 (m, 1H), 3.25 -3.06 (m, 1H), 2.85-2.75 (m, 1H), 2.41 (s, 3H), 2.35-2.30 (m, 1H), 2.11 (s , 3H)
(Isomer ratio 2) 9.20-9.10 (m, 1H), 8.75-8.65 (m, 1H), 8.27-8.17 (m, 1H), 7.45-7 .35 (m, 1H), 4.83-4.70 (m, 1H), 4.43-4.27 (m, 1H), 3.70-3.55 (m, 1H), 3.25 -3.06 (m, 1H), 2.85-2.75 (m, 1H), 2.53 (s, 3H), 2.35-2.30 (m, 1H), 2.08 (s , 3H)
1-019;
9.10 (d, J = 2.0 Hz, 1H), 8.66 (dd, J = 4.8, 1.6 Hz, 1H), 8.17 (ddd, J = 8.0, 2.0, 1.6 Hz, 1H), 7.38 (dd, J = 8.0, 4.8 Hz, 1H), 4.30 (d, J = 2.0 Hz, 2H), 4.00 (q, J = 9) .2 Hz, 2 H), 2.79 (s, 3 H), 2.40 (s, 3 H), 2.31 (t, J = 2.0 Hz, 1 H)
1-021;
9.12 (s, 1H), 8.71 (d, J = 4.8 Hz, 1H), 8.25-8.15 (m, 1H), 7.42 (dd, J = 8.0, 4 0.8 Hz, 1H), 4.34 (d, J = 2.4 Hz, 2H), 4.01 (q, J = 8.8 Hz, 2H), 2.83 (s, 3H), 2.33 (t , J = 2.4Hz, 1H)
1-022;
9.12 (brs, 1H), 8.67 (dd, J = 4.8, 1.2 Hz, 1H), 8.21 (dd, J = 8.0, 1.2 Hz, 1H), 7.39 (Dd, J = 8.0, 4.8 Hz, 1H), 4.80-4.50 (m, 1H), 4.50-4.15 (m, 1H), 3.60-3.35 ( m, 1H), 2.65-2.25 (m, 6H), 1.48 (d, J = 6.0 Hz, 3H), 1.17 (t, J = 7.6 Hz, 3H)
1-023;
9.14 (brs, 1H), 8.73 (dd, J = 4.8, 2.0 Hz, 1H), 8.23 (dd, J = 8.0, 2.0 Hz, 1H), 7.43 (Dd, J = 8.0, 4.8 Hz, 1H), 4.95 (d, J = 16.0 Hz, 1H), 4.12 (d, J = 16.0 Hz, 1H), 3.50− 3.30 (m, 1H), 2.34 (s, 1H), 2.09 (s, 3H), 1.49 (d, J = 6.8 Hz, 3H)
1-026;
9.15 (brs, 1H), 8.73 (d, J = 4.8 Hz, 1H), 8.24 (d, J = 8.0 Hz, 1H), 7.44 (dd, J = 8.0) , 4.8 Hz, 1H), 4.96 (d, J = 17.6 Hz, 1H), 4.12 (d, J = 17.6 Hz, 1H), 3.50-3.35 (m, 1H) , 2.75-2.50 (m, 2H), 2.34 (s, 1H), 1.52 (d, J = 6.4 Hz, 3H), 1.20 (t, J = 7.6 Hz, 3H)
1-027;
(Isomer ratio 9) 9.20-9.05 (m, 1H), 8.80-8.60 (m, 1H), 8.30-8.10 (m, 1H), 7.55-7 .35 (m, 1H), 5.10-4.75 (m, 1H), 4.40-3.90 (m, 1H), 4.10-3.90 (m, 1H), 3.00 -2.50 (m, 2H), 2.35 (s, 1H), 1.80-1.15 (m, 6H)
(Isomer ratio 1) 9.20-9.05 (m, 1H), 8.80-8.60 (m, 1H), 8.30-8.10 (m, 1H), 7.55-7 .35 (m, 1H), 5.10-4.75 (m, 1H), 4.40-3.90 (m, 1H), 3.60-3.45 (m, 1H), 3.00 -2.50 (m, 2H), 2.35 (s, 1H), 1.80-1.15 (m, 6H)
1-032;
(Isomer ratio 9) 9.20-9.10 (m, 1H), 8.80-8.65 (m, 1H), 8.27-8.15 (m, 1H), 7.47-7 .36 (m, 1H), 5.20-4.95 (m, 1H), 4.23-3.85 (m, 2H), 3.68-3.43 (m, 1H), 3.10 -2.87 (m, 1H), 2.71 (s, 3H), 2.35 (brs, 1H)
(Isomer ratio 1) 9.20-9.10 (m, 1H), 8.80-8.65 (m, 1H), 8.27-8.15 (m, 1H), 7.47-7 .36 (m, 1H), 5.20-4.95 (m, 1H), 4.23-3.85 (m, 2H), 3.68-3.43 (m, 1H), 3.10 -2.87 (m, 1H), 2.67 (s, 3H), 2.35 (brs, 1H)
1-036;
9.11 (brs, 1H), 8.64 (d, J = 4.8 Hz, 1H), 8.36 (d, J = 8.0 Hz, 1H), 7.57 (dd, J = 8.0) , 4.8 Hz, 1H), 4.65-4.40 (m, 2H), 2.71 (s, 1H), 2.65-2.35 (m, 3H), 2.43 (s, 3H) ), 1.75-1.65 (m, 1H), 1.60-1.45 (m, 1H), 1.40-1.15 (m, 3H), 1.15-0.95 (m) , 1H)
1-038;
9.11 (brs, 1H), 8.67 (d, J = 4.8 Hz, 1H), 8.20 (d, J = 8.0 Hz, 1H), 7.39 (dd, J = 8.0) , 4.8 Hz, 1H), 4.65-4.30 (m, 2H), 3.10-2.90 (m, 3H), 2.55-2.25 (m, 4H), 2.30. (S, 1H), 1.95-1.30 (m, 2H), 1.39 (t, J = 7.6 Hz, 3H)
1-039;
9.16 (d, J = 1.2 Hz, 1H), 8.76 (d, J = 4.8 Hz, 1H), 8.26 (dd, J = 8.0, 1.2 Hz, 1H), 7 .46 (dd, J = 8.0, 4.8 Hz, 1H), 4.96 (brs, 1H), 4.15 (brs, 1H), 2.75-2.45 (m, 3H), 2 .35 (s, 1H), 1.75-1.60 (m, 1H), 1.40-1.05 (m, 5H)
1-040;
(Isomer ratio 1) 9.13 (brs, 1H), 8.72 (brs, 1H), 8.23 (d, J = 8.0 Hz, 1H), 7.50-7.40 (m, 1H) ), 4.92 (brs, 1H), 4.14 (brs, 1H), 2.85-2.65 (m, 3H), 2.35 (s, 1H), 2.35-2.20 ( m, 1H), 1.80-1.60 (m, 1H), 1.45-1.20 (m, 4H)
(Isomer ratio 1) 9.13 (brs, 1H), 8.72 (brs, 1H), 8.23 (d, J = 8.0 Hz, 1H), 7.50-7.40 (m, 1H) ), 4.92 (brs, 1H), 4.14 (brs, 1H), 2.85-2.65 (m, 3H), 2.35 (s, 1H), 2.05-1.95 ( m, 1H), 1.60-1.50 (m, 1H), 1.45-1.20 (m, 4H)
1-041;
9.15 (brs, 1H), 8.75 (d, J = 4.8 Hz, 1H), 8.25 (d, J = 8.0 Hz, 1H), 7.45 (dd, J = 8.0) , 4.8 Hz, 1H), 4.92 (brs, 1H), 4.15 (brs, 1H), 3.15-3.00 (m, 3H), 2.40-2.20 (m, 2H) ), 1.75-1.55 (m, 2H), 1.42 (t, J = 7.6 Hz, 3H)
1-042;
9.16 (brs, 1H), 8.74 (d, J = 4.8 Hz, 1H), 8.30-8.15 (m, 1H), 7.44 (dd, J = 8.0, 4 .8 Hz, 1H), 4.99 (d, J = 18.4 Hz, 1H), 4.04 (d, J = 18.4 Hz, 1H), 3.00-2.65 (m, 2H), 2 .33 (s, 1H), 2.25-1.95 (m, 1H), 1.35-1.15 (m, 3H)
2-002;
9.14 (brs, 1H), 8.71 (d, J = 4.5 Hz, 1H), 8.30-8.15 (m, 1H), 7.50-7.35 (m, 1H), 5.20-4.80 (m, 1H), 4.30-3.90 (m, 1H), 3.35-3.10 (m, 2H), 2.65-2.55 (m, 4H) ), 2.33 (brs, 1H), 1.40-1.20 (m, 3H)
―――――――――――――――――――――――――――――――――――――――
The proton nuclear magnetic resonance chemical shift values in Table 4 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 investigated, 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.
Compound of the present invention: 1-001 to 1-020, 1-022 to 1-042, 2-001, 2-002
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, and the chemical solution is prepared using a rotary spray tower. 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: 1-001 to 1-016, 1-019, 1-022 to 1-032, 1-034 to 1-042, 2-001, 2-002
Test Example 3 Insecticidal test against peach aphid A moist absorbent cotton is laid on a glass petri dish with an inner diameter of 3 cm, and a kanran leaf cut out to the same diameter is placed thereon, and four mosquito aphids (Myzus persicae) adults are released. did. One day later, a 10% emulsion of the compound of the present invention (depending on the compound, 10% wettable powder was tested) 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 1-012, 1-014 to 1-019, 1-021 to 1-042, 2-001, 2-002
Test Example 4 Insecticidal test against cotton aphids Wet cotton wool with a 3 cm inner diameter petri dish, and a cucumber leaf cut to the same diameter was placed on it, and four cotton aphids (Aphis gossypii) adults were released. One day later, a 10% emulsion of the compound of the present invention (depending on the compound, 10% wettable powder was tested) 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 1-029, 1-031, 1-034 to 1-042, 2-001, 2-002
Test Example 5 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 Cai: 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: 1-003, 1-005, 1-006, 1-008, 1-018, 1-020, 1-021, 2-001, 2-002

  The novel thiazole 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 and R ³ each independently represent a hydrogen atom, a halogen atom, cyano, nitro, —OH, —SH, —NH ₂ , —CHO, —C (O) OH, —C (O) NH ₂ , — _{C (S) NH 2, -S} (O) 2 NH 2, C 1 ~C 6 ^alkyl, optionally substituted by ^{R 28a} _(C 1 ~C _{6) alkyl,} C 3 -C ₈ ^{cycloalkyl, R 28a} (C ₃ -C ₈ ) cycloalkyl, C ₂ -C ₆ alkenyl, optionally substituted by R ^28a (C ₂ -C ₆ ) alkenyl, C ₃ -C ₈ cycloalkenyl, R ^28a optionally substituted by _(C 3 ~C _{8) cycloalkenyl,} C 2 -C ₆ ^alkynyl, optionally substituted by ^{R 28a} _(C 2 ~C _{6) alkynyl,} C 1 -C _{6 alkoxy, C} 1 ~ C ₆ halo _Alkoxy, 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 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 alkylaminocarbonyl, di _(C 1 -C ₆ alkyl) _{aminocarbonyl,} C 1 -C ₆ alkylamino , di _(C 1 -C ₆ alkyl) amino, phenyl, (Z) phenyl substituted by _q , naphthyl, (Z) naphthyl substituted by _q , D1-32, D1-33, D1-34, D1-35, D1-36, D1-37, D1-38, D1-39 , D1-79, D1-80, D1-81, D1-82, D1-84, D1-85, D1-87, D1-92, D1-93, D1-95, D1-96 or D1-98 ,
R ² is a halogen atom, cyano, nitro, —OH, —SH, —NH ₂ , —CHO, —C (O) OH, —C (O) NH ₂ , —C (S) NH ₂ , —S ( _{O) 2 NH 2, C 1} ~C 6 ^alkyl, optionally substituted by ^{R 28a} _(C 1 ~C _{6) alkyl,} optionally substituted by C 3 -C ₈ ^{cycloalkyl, R 28a} _(C 3 ~ C _{8) cycloalkyl,} C 2 -C ₆ ^alkenyl, optionally substituted by ^{R 28a} _(C 2 ~C _{6) alkenyl,} C 3 -C ₈ ^{cycloalkenyl,} optionally substituted by ^{R 28a} _(C 3 ~ C _{8) cycloalkenyl,} C 2 -C ₆ ^alkynyl, optionally substituted by ^{R 28a} _(C 2 ~C _{6) alkynyl,} C 1 -C _{6 alkoxy,} C 1 -C _{6 haloalkoxy,} C 1 -C ₆ Alkyl _Thio, 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 halocycloalkyl _carbonyl, C 1 -C _{6 alkoxycarbonyl,} C 1 -C _{6 haloalkoxycarbonyl,} C 1 -C ₆ alkyl Aminosulfonyl, di (C ₁ -C ₆ alkyl) aminosulfonyl, C ₁ -C ₆ alkylaminocarbonyl, di (C ₁ -C ₆ alkyl) aminocarbonyl, C ₁ -C ₆ alkylamino, di (C ₁ -C ₆ alkyl) amino, phenyl, phenyl substituted by _{(Z) q,} Fuchiru, naphthyl substituted by _{(Z) q, D1-32, D1-33} , D1-34, D1-35, D1-36, D1-37, D1-38, D1-39, D1-79, D1- 80, D1-81, D1-82, D1-84, D1-85, D1-87, D1-92, D1-93, D1-95, D1-96 or D1-98, n is an integer of 2 or more Each R ² may be the same as or different from each other;
R ^{a is} optionally substituted by optionally substituted by ^{R 5a} _(C 1 ~C _{6) alkyl,} C 2 -C ₆ alkynyl, or ^{R 5b} _(C 2 ~C ₆₎ alkynyl,
R ^b is —C (O) OR ^6a , —C (O) R ⁷ , —C (S) R ⁷ , —C (O) N (R ⁸ ) R ^8a or —C (S) N (R ⁸ ) ^Represents R ^8a
R ^5a represents —OR ¹¹ or —S (O) _r R ¹¹ ,
R ^5b is a halogen atom, —OR ¹¹ or —S (O) _r R ^11.
R ^6a represents C ₁ -C ₆ alkyl or (C ₁ -C ₆ ) alkyl optionally substituted with R ¹⁴ ;
R ⁷ is a hydrogen _atom, C 1 -C ₆ ^alkyl, optionally substituted by ^{R 14} _(C 1 ~C _{6) alkyl,} C 3 -C ₈ ^cycloalkyl, optionally substituted by ^{R 14} _{(C 3} -C ₈₎ cycloalkyl _,, C 2 -C ₆ ^alkenyl, optionally substituted by ^{R 14} _(C 2 ~C _{6) alkenyl,} C 3 -C ₈ ^{cycloalkenyl,} optionally substituted by ^{R 14} (C ₃ -C _{8) cycloalkenyl,} optionally substituted by C 2 -C _{6 ^{alkynyl, R 14 (C 2 ~C 6}} ) alkynyl, phenyl, phenyl substituted by _{(Z) q,} naphthyl, _{(Z) q} Naphthyl substituted by D1-32, D1-33, D1-34, D1-35, D1-36, D1-37, D1-38, D1-39, D1-79, D1-80, D1-81, D1-82, D1-84, D1-85, D1-87, D1-92, D1-93, D1-95, D1-96 or D1-98,
R ⁸ is a hydrogen _atom, C 1 -C ₆ ^alkyl, optionally substituted by ^{R 14} _(C 1 ~C _{6) alkyl,} C 3 -C ₈ ^cycloalkyl, optionally substituted by ^{R 14} _{(C 3} -C ₈₎ cycloalkyl _,, C 2 -C ₆ ^alkenyl, optionally substituted by ^{R 14} _(C 2 ~C _{6) alkenyl,} C 3 -C ₈ ^{cycloalkenyl,} optionally substituted by ^{R 14} (C ₃ -C ₈ ) cycloalkenyl, C ₂ -C ₆ alkynyl or (C ₂ -C ₆ ) alkynyl optionally substituted by R ¹⁴ ,
R ^8a is a hydrogen _atom, C 1 -C ₆ ^alkyl, optionally substituted by ^{R 14a} _(C 1 ~C ₆₎ alkyl, phenyl, phenyl substituted by _{(Z) q,} naphthyl, the _{(Z) q} Substituted naphthyl, D1-32, D1-33, D1-34, D1-35, D1-36, D1-37, D1-38, D1-39, D1-79, D1-80, D1-81, D1 -82, D1-84, D1-85, D1-87, D1-92, D1-93, D1-95, D1-96 or D1-98,
R ¹¹ represents C ₂ -C ₆ alkynyl or (C ₂ -C ₆ ) alkynyl optionally substituted by R ^14c ,
R ¹⁴ is halogen atom, ^{cyano, -OH, -OR 15, -SH,} -S (O) r R 15, phenyl, substituted phenyl, naphthyl, the _{(Z) q} is substituted by _{(Z) q} Naphthyl, D1-79, D1-80, D1-81, D1-82, D1-84, D1-85, D1-87, D1-92, D1-93, D1-95, D1-96 or D1-98 Represent,
R ^14a represents a halogen atom, cyano, —OH, —OR ^15a , —SH or —S (O) _r R ^15a ,
R ^14c represents a halogen atom, cyano, —OH, —OR ^15c , —SH or —S (O) _r R ^15c ,
R ¹⁵ _is, C 1 -C _{6 alkyl,} C 1 -C ₆ haloalkyl, phenyl, _(Z) phenyl substituted by _q, naphthyl, naphthyl substituted by _{(Z) q, D1-32, D1-33} , D1-34, D1-35, D1-36, D1-37, D1-38 or D1-39,
R ^15a and R ^15c each independently represent C ₁ -C ₆ alkyl;
D1-32, D1-33, D1-34, D1-35, D1-36, D1-37, D1-38, D1-39, D1-79, D1-80, D1-81, D1-82, D1- 84, D1-85, D1-87, D1-92, D1-93, D1-95, D1-96 and D1-98 each represent a ring represented by the following structural formula,

X ¹ and X ^1b are each independently 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 represent _alkylthio, C 1 -C _{6 haloalkylthio,} C 1 -C _{6 alkylsulfinyl,} C 1 -C _{6 haloalkylsulfinyl,} a C 1 -C ₆ alkylsulfonyl or _C 1 -C ₆ haloalkylsulfonyl, g1 or when g4 represents an integer of 2 or more, each X ¹ may be also or different from each other the same as each other, or, f5, f7 or When 9 represents an integer of 2 or more, each X ^1b may be or different from each other the same as each other, further, when two which X ^1b are substituted on the same carbon, the two X ^1b oxo together, thioxo, _imino, C 1 -C _{6 alkylimino,} may form a C 1 -C ₆ alkoxyimino or _C 1 -C ₆ alkylidene,
Z 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 to} C ₆ haloalkylthio, C _{1 to} C ₆ alkylsulfinyl, C _{1 to} C ₆ haloalkylsulfinyl, C _{1 to} C ₆ alkylsulfonyl or C _{1 to} C ₆ haloalkylsulfonyl, and q represents an integer of 2 or more Each Z may be the same as or different from each other;
R ^28a represents a halogen atom, —OH, —OR ²⁹ , —SH or —S (O) _r R ²⁹ ,
R ²⁹ represents C ₁ -C ₆ alkyl,
g1 and n each independently represent an integer of 0, 1, 2, or 3;
g4 represents an integer of 0, 1, 2, 3 or 4;
f5 represents an integer of 0, 1, 2, 3, 4 or 5,
f7 represents an integer of 0, 1, 2, 3, 4, 5, 6 or 7,
f9 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9,
q represents an integer of 1, 2, 3, 4 or 5;
m1, m2 and m3 each independently represent an integer of 0 or 1,
r and r2 each independently represents an integer of 0, 1 or 2. Or a salt thereof. A ¹ represents -CR ¹
R ¹ and R ³ each independently represent a hydrogen atom, a halogen atom or C ₁ -C ₆ alkyl;
The thiazole 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,
R ³ represents a hydrogen atom, a halogen atom or C ₁ -C ₆ alkyl,
R ^a represents C ₂ -C ₆ alkynyl,
R ^b represents —C (O) OR ^6a , —C (O) R ⁷ or —C (O) N (R ⁸ ) R ^8a ,
R ^6a represents C ₁ -C ₆ alkyl;
R ⁷ _is, C 1 -C ₆ ^alkyl, optionally substituted by ^{R 14} _(C 1 ~C ₆₎ ^alkyl, optionally by optionally substituted by ^{R 14} _(C 2 ~C ₆₎ alkenyl or ^{R 14} Represents substituted (C ₃ -C ₈ ) cycloalkyl,
R ⁸ represents (C ₁ -C ₆ ) alkyl optionally substituted with R ¹⁴ ;
R ^8a represents a hydrogen atom or C ₁ -C ₆ alkyl;
R ¹⁴ represents a halogen atom or —S (O) _r R ¹⁵ ;
R ¹⁵ represents C ₁ -C ₆ alkyl,
m1 and n represent 0;
The thiazole derivative or a salt thereof according to claim 2, wherein r represents an integer of 0, 1 or 2.   The pest control agent which contains the 1 type (s) or 2 or more types chosen from the thiazole derivative and its salt of Claims 1-3 as an active ingredient.   The agrochemical which contains 1 type, or 2 or more types chosen from the thiazole derivative and its salt of Claims 1-3 as an active ingredient.   An internal or ectoparasite control agent for mammals or birds containing one or more selected from the thiazole derivatives according to claim 1 and a salt thereof as active ingredients.   An insecticide or acaricide containing, as an active ingredient, one or more selected from the thiazole derivatives according to claim 1 and a salt thereof.   The soil treatment agent which contains the 1 type (s) or 2 or more types chosen from the thiazole 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.