JP2020111539A - Condensed heterocyclic compound and pest control agent - Google Patents

Abstract

To provide a condensed heterocyclic compound and a salt thereof, and a pest control agent containing the compound as an active ingredient.SOLUTION: There is provided the compound of the following general formula (1), for example, 2-[3-(ethylsulfonyl)-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-7-(trifluoromethyl)imidazo[1,2-c]pyrimidine. In the formula (1), D is a ring represented by any of D1 to D3 and Q is a ring represented by any of Q1 to Q4.SELECTED DRAWING: None

Description

TECHNICAL FIELD The present invention relates to a novel fused heterocyclic compound and salts thereof, and a pest control agent containing the compound as an active ingredient.

For example, Patent Documents 1 to 31 disclose fused heterocyclic compounds, but do not disclose fused heterocyclic compounds according to the present invention. Further, its usefulness as a pest control agent, in particular, an insecticide/miticide and an agent for controlling internal or external parasites of mammals or birds is not known at all.

International Publication No. 2016/005263 International Publication No. 2015/198859 International Publication No. 2015/133603 International Publication No. 2015/121136 International Publication No. 2015/091945 International Publication No. 2015/087458 International Publication No. 2015/071180 International Publication No. 2015/059088 International Publication No. 2015/002211 International Publication No. 2015/000715 International Publication No. 2014/157600 International Publication No. 2014/148451 International Publication No. 2014/142292 International Publication No. 2014/1329772 International Publication No. 2014/132971 International Publication No. 2014/123206 International Publication No. 2014/123205 International Publication No. 2014/104407 International Publication No. 2013/180194 International Publication No. 2013/180193 International Publication No. 2013/191113 International Publication No. 2013/191189 International Publication No. 2013/191112 International Publication No. 2013/191188 International Publication No. 2013/018928 International Publication No. 2012/086848 International Publication No. 2012/074135 International Publication No. 2011-162364 International Publication No. 2011/043404 International Publication No. 2010/125985 International Publication No. 2009/131237

Development of pest control agents for the purpose of controlling various pests such as agricultural and horticultural pests, forest pests, and sanitary pests has progressed, and a wide variety of drugs have been put to practical use until now.

However, due to the long-term use of such chemicals, pests have acquired drug resistance in recent years, and the number of scenes in which it has become difficult to control the existing insecticides and bactericides that have been conventionally used has been increasing. In addition, some of existing pesticides are highly toxic, or some of them remain in the environment for a long period of time, causing a problem of disturbing the ecosystem. Under such circumstances, it is always expected to develop a novel pest control agent having not only a high pest control activity but also low toxicity and low residue.

The object of the present invention is to provide a novel pest control which exhibits excellent pest control activity, has low toxicity such as having almost no adverse effect on non-target organisms such as mammals, fish and beneficial insects, and has low persistence. It is to provide the agent.

As a result of intensive studies aimed at solving the above problems, the present inventors have found that the novel fused heterocyclic compound represented by the following formula (1) according to the present invention has excellent pest control activity, particularly insecticidal activity. The present invention has been completed by finding that they are extremely useful compounds that exhibit acaricidal activity and have almost no adverse effect on non-target organisms such as mammals, fish and beneficial insects.

That is, the present invention relates to the following [1] to [25].

[1]
Formula (1):

[In the formula, D substituted with -S(O) _n R ¹ represents a ring represented by any one of D 1, D 2 and D 3,

Q represents a ring represented by any of Q1, Q2, Q3 or Q4,

G ₁ represents a nitrogen atom or C(Y1),
G ₂ represents a nitrogen atom or C(Y2),
G ₃ represents a nitrogen atom or C(Y3),
G ₄ represents a nitrogen atom or C(Y4),
G ₅ represents a nitrogen atom or C(Y5),
T ₁ represents N(T _1a ), an oxygen atom or a sulfur atom,
A ¹ represents N(A ^1a ), an oxygen atom or a sulfur atom,
A ² represents a nitrogen atom or C(R ² ),
A ³ represents a nitrogen atom or C(R ³ ),
A ⁴ represents a nitrogen atom or C(R ⁴ ),
A ⁵ represents a nitrogen atom or C(R ⁵ ),
A ⁸ represents a nitrogen atom or C(R ⁸ ),
R ¹ is C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, (C ₁ -C ₆ )alkyl optionally substituted with R ^1a , C ₂ -C ₆ alkenyl, C ₂ -C ₆ haloalkenyl, C ₂ -C _{6 alkynyl,} C 2 -C _{6 haloalkynyl,} C 3 -C _{6 cycloalkyl,} C 3 -C _{6 halocycloalkyl,} C 3 -C ₆ cycloalkyl _(C 1 -C ₆₎ alkyl, _{C 3} Represents a -C ₆ halocycloalkyl(C ₁ -C ₆ )alkyl or hydroxy(C ₁ -C ₆ )alkyl,
R ^1a represents C ₁ -C ₈ alkoxy, C ₁ -C ₈ haloalkoxy, C ₁ -C ₈ alkoxycarbonyl, C ₁ -C ₆ alkylthio, C ₁ -C ₆ haloalkylthio, C ₁ -C ₆ alkylsulfinyl, Represents C ₁ -C ₆ haloalkylsulfinyl, C ₁ -C ₆ alkylsulfonyl, C ₁ -C ₆ haloalkylsulfonyl or cyano,
R ² is a hydrogen atom, a halogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₈ alkoxy, C ₁ -C ₈ haloalkoxy, C ₃ -C ₆ cycloalkyl, C ₃ -. C _{6 halocycloalkyl,} C 1 -C _{6 alkylthio,} C 1 -C _{6 haloalkylthio,} C 1 -C _{6 alkylsulfinyl,} C 1 -C _{6 haloalkylsulfinyl,} C 1 -C _{6 alkylsulfonyl,} C 1 -C ₆ It represents ^{haloalkylsulfonyl, -C (O) R 20a,} -C (O) OH, ^{_{hydroxy, -NH 2, -NHR 20g, -N}} (R 20h) R 20g, mercapto, cyano or nitro,
R ³ is a hydrogen atom, a halogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₂ -C ₆ haloalkenyl, C ₂ -C ₆ haloalkynyl, C ₁ -C ₈ alkoxy, C ₁ -. C ₈ haloalkoxy, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ halocycloalkyl, C ₁ -C ₆ alkylthio, C ₁ -C ₆ haloalkylthio, optionally substituted by R ^3a (C ₁ -C _{6) alkylthio,} C 1 -C _{6 alkylsulfinyl,} C 1 -C _{6 haloalkylsulfinyl,} C 1 -C _{6 alkylsulfonyl,} C 1 -C ₆ ^{haloalkylsulfonyl, -C (O) R 30a,} -C (O) OH , ^{_{hydroxy, -OC (O) R 30e,}} -OS (O) 2 R 30f, -NH 2, -NHR 30g, -N (R 30h) R 30g, ^{mercapto, -SC (O) R 30i,} -SF 5 represents cyano, nitro, phenyl, phenyl optionally substituted by R ^3b, a heterocyclic ring optionally substituted by heterocycle or R ^3b,
R ^3a represents C ₁ -C ₈ alkoxycarbonyl,
R ^3b represents a halogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₈ alkoxy, C ₁ -C ₈ haloalkoxy, cyano or nitro,
R ⁴ represents a hydrogen atom, a halogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₂ -C ₆ haloalkenyl, C ₂ -C ₆ haloalkynyl, C ₁ -C ₈ alkoxy, C ₁ -. C ₈ haloalkoxy, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ halocycloalkyl, C ₁ -C ₆ alkylthio, C ₁ -C ₆ haloalkylthio, optionally substituted by R ^4a (C ₁ -C _{6) alkylthio,} C 1 -C _{6 alkylsulfinyl,} C 1 -C _{6 haloalkylsulfinyl,} C 1 -C _{6 alkylsulfonyl,} C 1 -C ₆ ^{haloalkylsulfonyl, -C (O) R 40a,} -C (O) OH , ^{_{hydroxy, -OC (O) R 40e,}} -OS (O) 2 R 40f, -NH 2, -NHR 40g, -N (R 40h) R 40g, ^{mercapto, -SC (O) R 40i,} -SF 5 represents cyano, nitro, phenyl, phenyl optionally substituted by R ^4b, a heterocyclic ring optionally substituted by heterocycle or R ^4b,
R ^4a represents C ₁ -C ₈ alkoxycarbonyl,
R ^4b represents a halogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₈ alkoxy, C ₁ -C ₈ haloalkoxy, cyano or nitro,
R ⁵ is a hydrogen atom, a halogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₈ alkoxy, C ₁ -C ₈ haloalkoxy, C ₃ -C ₆ cycloalkyl, C ₃ -. C _{6 halocycloalkyl,} C 1 -C _{6 alkylthio,} C 1 -C _{6 haloalkylthio,} C 1 -C _{6 alkylsulfinyl,} C 1 -C _{6 haloalkylsulfinyl,} C 1 -C _{6 alkylsulfonyl,} C 1 -C ₆ It represents ^{haloalkylsulfonyl, -C (O) R 50a,} -C (O) OH, ^{_{hydroxy, -NH 2, -NHR 50g, -N}} (R 50h) R 50g, mercapto, cyano or nitro,
R ⁶ is a hydrogen atom, a halogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₈ alkoxy, C ₁ -C ₈ haloalkoxy, C ₃ -C ₆ cycloalkyl, C ₃ -. C _{6 halocycloalkyl,} C 1 -C _{6 alkylthio,} C 1 -C _{6 haloalkylthio,} C 1 -C _{6 alkylsulfinyl,} C 1 -C _{6 haloalkylsulfinyl,} C 1 -C _{6 alkylsulfonyl,} C 1 -C ₆ It represents ^{haloalkylsulfonyl, -C (O) R 60a,} -C (O) OH, ^{_{hydroxy, -NH 2, -NHR 60g, -N}} (R 60h) R 60g, mercapto, cyano or nitro,
R ⁷ is a hydrogen atom, a halogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₈ alkoxy, C ₁ -C ₈ haloalkoxy, C ₁ -C ₆ alkylthio, C ₁ -C. ₆ haloalkylthio, C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ haloalkylsulfinyl, C ₁ -C ₆ alkylsulfonyl, C ₁ -C ₆ haloalkylsulfonyl, mercapto, -SF ₅ , cyano or nitro,
R ⁸ represents a hydrogen atom, a halogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₈ alkoxy, C ₁ -C ₈ haloalkoxy or cyano,
A ^1a is optionally substituted by hydrogen _atom, C 1 -C _{6 alkyl,} C 1 -C ₆ ^haloalkyl, optionally substituted by _{^{A 1a-a (C 1 -C}} 6) ^{alkyl, A 1a-a} _(C 1 -C _{6) haloalkyl,} C 2 -C _{6 alkenyl,} C 2 -C _{6 haloalkenyl,} C 2 -C _{6 alkynyl,} C 2 -C _{6 haloalkynyl,} C 1 -C _{8 alkoxy,} C 1 -C ₈ haloalkoxy, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ halocycloalkyl, C ₃ -C ₆ cycloalkyl(C ₁ -C ₆ )alkyl, C ₃ -C ₆ halocycloalkyl (C ₁ -C) _{6) alkyl,} C 1 -C _{6 alkylthio,} C 1 -C _{6 haloalkylthio,} C 1 -C _{6 alkylsulfinyl,} C 1 -C _{6 haloalkylsulfinyl,} C 1 -C _{6 alkylsulfonyl,} C 1 -C ₆ haloalkylsulfonyl , C(O)R ^10a , hydroxy or cyano,
A ^1a-a is C ₁ -C ₈ alkoxy, C ₁ -C ₈ haloalkoxy, C ₁ -C ₈ alkoxycarbonyl, C ₁ -C ₈ haloalkoxycarbonyl, C ₁ -C ₆ alkylcarbonyl, C ₁ -C. ₆ haloalkylcarbonyl, C ₁ -C ₆ alkylthio, C ₁ -C ₆ haloalkylthio, C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ haloalkylsulfinyl, C ₁ -C ₆ alkylsulfonyl, C ₁ -C ₆ haloalkylsulfonyl Represents hydroxy, cyano,
T _1a represents a hydrogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ haloalkenyl, C ₂ -C ₆ alkynyl, C ₂ -C ₆ haloalkynyl. , C ₁ -C ₈ alkoxy, C ₁ -C ₈ haloalkoxy, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ halocycloalkyl, C ₃ -C ₆ cycloalkyl(C ₁ -C ₆ )alkyl or C Represents a _3- C ₆ halocycloalkyl(C ₁ -C ₆ )alkyl,
Y1, Y2, Y3 and Y4 are each independently a hydrogen atom, a halogen _atom, C 1 -C _{6 alkyl,} C 1 -C ₆ haloalkyl, optionally substituted by ^{Y a} _(C 1 -C ₆₎ alkyl , optionally substituted by ^{Y a} _(C 1 -C _{6) haloalkyl,} C 2 -C _{6 alkenyl,} C 2 -C ₆ haloalkenyl, optionally substituted by ^{Y a} _(C 2 -C ₆₎ alkenyl, C ₂ -C _{6 alkynyl,} C 2 -C ₆ haloalkynyl, optionally substituted by ^{Y b} _(C 2 -C _{6) alkynyl,} C 1 -C _{8 alkoxy,} C 1 -C ₈ haloalkoxy, by ^{Y a} Optionally substituted (C ₁ -C ₈ )alkoxy, C ₂ -C ₆ alkenyloxy, C ₂ -C ₆ haloalkenyloxy, (C ₂ -C ₆ )alkenyloxy optionally substituted with Y ^a , C ₂ -C _{6 alkynyloxy,} C 2 -C ₆ haloalkynyloxy, optionally substituted by ^{Y a} _(C 2 -C _{6) alkynyloxy,} C 3 -C _{6 cycloalkyl,} C 3 -C ₆ halocycloalkyl , _C 3 -C ₆ cycloalkyl _(C 1 -C _{6) alkyl,} C 3 -C ₆ halocycloalkyl _(C 1 -C _{6) alkyl,} C 1 -C _{6 alkylthio,} C 1 -C ₆ haloalkylthio, Y optionally substituted by ^a _(C 1 -C _{6) alkylthio,} C 2 -C _{6 alkenylthio,} C 2 -C ₆ halo alkenylene _thio, C 2 -C _{6 alkynylthio,} C 2 -C ₆ halo alkynylene thio, C ₁ -C _{6 alkylsulfinyl,} C 1 -C ₆ haloalkylsulfinyl, optionally substituted by ^{Y a} _(C 1 -C _{6) alkylsulfinyl,} C 2 -C _{6 alkenylsulfinyl,} C 2 -C ₆ halo alkenylsulfinyl , _C 2 -C _{6 alkynylsulfinyl,} C 2 -C ₆ halo _{alkynylsulfinyl,} C 1 -C _{6 alkylsulfonyl,} C 1 -C ₆ haloalkylsulfonyl, optionally substituted by ^{Y a} _(C 1 -C ₆₎ alkyl _sulfonyl, C 2 -C _{6 alkenylsulfonyl,} C 2 -C ₆ haloalkenyl _sulfonyl, C 2 -C _{6 alkynylsulfonyl,} C 2 -C ₆ haloalkynyl sulfonyl, - C(O)R ^90a , -C(O)NHR ^90b , -C(O)N(R ^90c )R ^90b , -C(O)OH, -C(=NOR ^90d )R ^90a , -C(O). NH _{2, ^{hydroxy, -OC (O) R 90e,}} -OS (O) 2 R 90f, -NH 2, -NHR 90g, -N (R 90h) R 90g, ^{mercapto, -SC (O) R 90i,} - S(O) ₂ NHR ^90j , —S(O) ₂ N(R ^90k )R ^90j , ^—SF ₅ , cyano, nitro, phenyl, optionally substituted by Y ^c , phenyl, heterocycle or Y ^c . Represents a substituted heterocycle,
Y5 and Y6 are each independently a hydrogen atom, a halogen _atom, C 1 -C _{6 alkyl,} C 1 -C _{6 haloalkyl,} C 1 -C _{8 alkoxy,} C 1 -C _{8 haloalkoxy,} C 1 -C _{6 alkylthio,} C 1 -C _{6 haloalkylthio,} C 1 -C _{6 alkylsulfinyl,} C 1 -C _{6 haloalkylsulfinyl,} C 1 -C _{6 alkylsulfonyl,} C 1 -C ₆ haloalkylsulfonyl, mercapto, -SF _5, cyano, Represents phenyl optionally substituted by nitro, phenyl or Y ^c ,
Y ^a is C ₁ -C ₈ alkoxy, C ₁ -C ₈ haloalkoxy, C ₁ -C ₈ alkoxycarbonyl, C ₁ -C ₈ haloalkoxycarbonyl, C ₁ -C ₆ alkylcarbonyl, C ₁ -C ₆ haloalkyl. _carbonyl, C 1 -C _{6 alkylthio,} C 1 -C _{6 haloalkylthio,} C 1 -C _{6 alkylsulfinyl,} C 1 -C _{6 haloalkylsulfinyl,} C 1 -C _{6 alkylsulfonyl,} C 1 -C ₆ haloalkylsulfonyl, hydroxy Or represents cyano,
Y ^b represents C ₁ -C ₆ alkyl, C ₃ -C ₆ cycloalkyl, trimethylsilyl, C ₁ -C ₈ alkoxy, phenyl or phenyl optionally substituted by Y ^b2 ,
Y ^b2 represents C ₁ -C ₆ haloalkyl,
Y ^c represents a halogen _atom, C 1 -C _{6 alkyl,} C 1 -C _{6 haloalkyl,} C 1 -C _{8 alkoxy,} C 1 -C ₈ haloalkoxy, cyano or nitro,
R ^10a , R ^20a , R ^30a , R ^30e , R ^40a , R ^40e , R ^50a , R ^60a and R ^90a are each independently a hydrogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, Represents C ₁ -C ₈ alkoxy or C ₁ -C ₈ haloalkoxy,
^{R 20g, R 20h, R 30f} , R 30g, R 30h, R 30i, R 40f, R 40g, R 40h, R 40i, R 50g, R 50h, R 60g, R 60h, R 90b, R 90c, R 90i , R ^90j and R ^90k each independently represent C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
R ^90d represents a hydrogen atom, C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
R ^90e is a hydrogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₈ alkoxy, C ₁ -C ₈ haloalkoxy, C ₁ -C ₆ alkylamino, C ₁ -C ₆ haloalkyl. Represents amino, di(C ₁ -C ₆ )alkylamino or di(C ₁ -C ₆ )haloalkylamino,
R ^90f represents C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkylamino, C ₁ -C ₆ haloalkylamino, di(C ₁ -C ₆ )alkylamino or di(C ₁ -). C ₆₎ represents halo alkylamino,
R ^90g and R ^90h are each independently C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkylcarbonyl, C ₁ -C ₆ haloalkylcarbonyl, C ₁ -C ₈ alkoxycarbonyl, C ₁ -C _{8 haloalkoxycarbonyl,} C 1 -C ₆ alkylamino _carbonyl, C 1 -C ₆ haloalkylcarbonyl _{aminocarbonyl,} C 1 -C ₆ alkylamino _{thiocarbonyl,} C 1 -C ₆ haloalkylthio aminothiocarbonyl, phenylcarbonyl, C ₁ -C ₆ alkylsulfonyl, C ₁ -C ₆ haloalkylsulfonyl, C ₁ -C ₆ alkylaminosulfonyl or di(C ₁ -C ₆ )alkylaminosulfonyl is represented,
n represents an integer of 0, 1 or 2. ] The condensed heterocyclic compound represented by these, its salt, or those N-oxides.

[2]
D substituted with -S _(O) n ^{R 1} represents a ring represented by D1,
G ₁ represents C(Y1),
G ₂ represents C(Y2),
G ₃ represents C(Y3),
G ₄ represents C(Y4),
A ² represents C(R ² ),
A ³ represents C(R ³ ),
R ¹ is C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ haloalkenyl, C ₂ -C ₆ alkynyl, C ₂ -C ₆ haloalkynyl, C _3. -C ₆ cycloalkyl(C ₁ -C ₆ )alkyl or C ₃ -C ₆ halocycloalkyl(C ₁ -C ₆ )alkyl,
R ² represents a hydrogen atom, a halogen atom, C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
R ³ is a hydrogen atom, a halogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₈ alkoxy, C ₁ -C ₈ haloalkoxy, C ₁ -C ₆ alkylthio, C ₁ -C. ₆ haloalkylthio, (C ₁ -C ₆ )alkylthio optionally substituted by R ^3a , C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ haloalkylsulfinyl, C ₁ -C ₆ alkylsulfonyl or C ₁ -C ₆ Represents haloalkylsulfonyl,
R ⁴ is a hydrogen atom, a halogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₈ alkoxy, C ₁ -C ₈ haloalkoxy, C ₁ -C ₆ alkylthio, C ₁ -C. ₆ haloalkylthio, (C ₁ -C ₆ )alkylthio optionally substituted by R ^4a , C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ haloalkylsulfinyl, C ₁ -C ₆ alkylsulfonyl or C ₁ -C ₆ Represents haloalkylsulfonyl,
R ⁵ , R ⁶ and R ⁸ each independently represent a hydrogen atom, a halogen atom, C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
R ⁷ represents a hydrogen atom, a halogen atom or C ₁ -C ₆ haloalkyl,
A ^1a represents a hydrogen atom, C ₁ -C ₆ alkyl, (C ₁ -C ₆ )alkyl optionally substituted by A ^1a-a , C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -. Represents C ₈ alkoxy, C ₃ -C ₆ cycloalkyl or C(O)R ^10a ,
A ^1a-a represents C ₁ -C ₈ alkoxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ alkylsulfonyl or cyano,
R ^10a represents a hydrogen atom, C ₁ -C ₆ alkyl or C ₁ -C ₈ alkoxy,
Y1, Y2, Y3 and Y4 are each independently a hydrogen atom, a halogen _atom, C 1 -C _{6 alkyl,} C 1 -C _{6 haloalkyl,} C 2 -C _{6 alkenyl,} C 2 -C ₆ alkynyl, ^{Y b} optionally substituted _(C 2 -C ₆₎ alkynyl _by, C 1 -C _{8 alkoxy,} C 1 -C _{8 haloalkoxy,} C 1 -C _{6 alkylthio,} C 1 -C ₆ haloalkylthio, optionally by ^{Y a} Substituted (C ₁ -C ₆ )alkylthio, C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ haloalkylsulfinyl, C ₁ -C ₆ alkylsulfonyl, C ₁ -C ₆ haloalkylsulfonyl, —C(O)R ^{90a, -C (O) NHR 90b} , -C (O) N (R 90c) R 90b, -C (O) OH, ^{hydroxy, -OC (O) R 90e,} -OS (O) 2 R 90f, - ^{_{NH 2, -NHR 90g, -N (}} R 90h) R 90g, ^{_{mercapto, -SC (O) R 90i,}} -S (O) 2 NHR 90j, -S (O) 2 N (R 90k) R 90j, - SF _5, represents cyano, nitro, phenyl, phenyl optionally substituted by Y ^c, a heterocyclic ring optionally substituted by heterocycle or Y ^c,
Y ^a is, C ₁ -C ₈ alkoxycarbonyl represents a carbonyl [1], wherein the fused heterocyclic compound or a salt thereof or their N- oxide.

[3]
D substituted with —S(O) _n R ¹ represents a ring represented by D2,
Q represents a ring represented by Q1,
A ¹ represents N(A ^1a ),
A ² represents C(R ² ),
A ³ represents C(R ³ ),
A ⁴ represents C(R ⁴ ),
A ⁵ represents a nitrogen atom,
R ¹ is C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ haloalkenyl, C ₂ -C ₆ alkynyl, C ₂ -C ₆ haloalkynyl, C _3. -C ₆ cycloalkyl(C ₁ -C ₆ )alkyl or C ₃ -C ₆ halocycloalkyl(C ₁ -C ₆ )alkyl,
R ² represents a hydrogen atom, a halogen atom, C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
R ³ is a hydrogen atom, a halogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₈ alkoxy, C ₁ -C ₈ haloalkoxy, C ₁ -C ₆ alkylchi group, C ₁ -. C ₆ ^{haloalkylthio,} optionally substituted by ^{R 3a} _(C 1 -C _{6) alkylthio,} C 1 -C _{6 alkylsulfinyl,} C 1 -C _{6 haloalkylsulfinyl,} C 1 -C ₆ alkylsulfonyl or _C 1 -C ₆ represents haloalkylsulfonyl,
R ⁴ is a hydrogen atom, a halogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₈ alkoxy, C ₁ -C ₈ haloalkoxy, C ₁ -C ₆ alkylthio, C ₁ -C. ₆ haloalkylthio, (C ₁ -C ₆ )alkylthio optionally substituted by R ^4a , C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ haloalkylsulfinyl, C ₁ -C ₆ alkylsulfonyl or C ₁ -C ₆ Represents haloalkylsulfonyl,
A ^1a represents a hydrogen atom, C ₁ -C ₆ alkyl, (C ₁ -C ₆ )alkyl optionally substituted by A ^1a-a , C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -. Represents C ₈ alkoxy, C ₃ -C ₆ cycloalkyl or C(O)R ^10a ,
A ^1a-a represents C ₁ -C ₈ alkoxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ alkylsulfonyl or cyano,
R ^10a represents a hydrogen atom, C ₁ -C ₆ alkyl or C ₁ -C ₈ alkoxy,
Y5 represents a hydrogen atom, a halogen atom, C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
Y6 represents a hydrogen atom, a halogen atom, C ₁ -C ₆ haloalkyl, phenyl or Y ^c represents phenyl optionally substituted by [1], wherein the fused heterocyclic compound or a salt thereof or their N- oxide.

[4]
D substituted with —S(O) _n R ¹ represents a ring represented by D3,
Q represents a ring represented by Q1,
G ₁ represents C(Y1),
G ₂ represents C(Y2),
G ₃ represents C(Y3),
G ₄ represents C(Y4),
T ₁ represents N(T _1a ) or a sulfur atom,
A ¹ represents N(A ^1a ),
A ² represents C(R ² ),
A ³ represents C(R ³ ),
A ⁴ represents C(R ⁴ ),
A ⁵ represents a nitrogen atom,
R ¹ is C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ haloalkenyl, C ₂ -C ₆ alkynyl, C ₂ -C ₆ haloalkynyl, C _3. -C ₆ cycloalkyl(C ₁ -C ₆ )alkyl or C ₃ -C ₆ halocycloalkyl(C ₁ -C ₆ )alkyl,
R ² represents a hydrogen atom, a halogen atom, C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
R ³ is a hydrogen atom, a halogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₈ alkoxy, C ₁ -C ₈ haloalkoxy, C ₁ -C ₆ alkylthio, C ₁ -C. ₆ haloalkylthio, (C ₁ -C ₆ )alkylthio optionally substituted by R ^3a , C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ haloalkylsulfinyl, C ₁ -C ₆ alkylsulfonyl or C ₁ -C ₆ Represents haloalkylsulfonyl,
R ⁴ is a hydrogen atom, a halogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₈ alkoxy, C ₁ -C ₈ haloalkoxy, C ₁ -C ₆ alkylthio, C ₁ -C. ₆ haloalkylthio, (C ₁ -C ₆ )alkylthio optionally substituted by R ^4a , C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ haloalkylsulfinyl, C ₁ -C ₆ alkylsulfonyl or C ₁ -C ₆ Represents haloalkylsulfonyl,
A ^1a represents a hydrogen atom, C ₁ -C ₆ alkyl, (C ₁ -C ₆ )alkyl optionally substituted by A ^1a-a , C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -. Represents C ₈ alkoxy, C ₃ -C ₆ cycloalkyl or C(O)R ^10a ,
A ^1a-a represents C ₁ -C ₈ alkoxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ alkylsulfonyl or cyano,
R ^10a represents a hydrogen atom, C ₁ -C ₆ alkyl or C ₁ -C ₈ alkoxy,
T _1a represents a hydrogen atom or C ₁ -C ₆ alkyl,
Y1, Y2, Y3 and Y4 are each independently a hydrogen atom, a halogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₈ alkoxy, C ₁ -C ₈ haloalkoxy, C. ₁ -C _{6 alkylthio,} C 1 -C _{6 haloalkylthio,} C 1 -C _{6 alkylsulfinyl,} C 1 -C _{6 haloalkylsulfinyl,} C 1 -C _{6 alkylsulfonyl,} C 1 -C ₆ haloalkylsulfonyl, cyano or nitro The condensed heterocyclic compound represented by [1] or a salt thereof or an N-oxide thereof.

[5]
Q represents a ring represented by Q1,
A ¹ represents N(A ^1a ),
R ¹ represents C ₁ -C ₆ alkyl,
R ³ represents a hydrogen atom, a halogen _atom, C 1 -C _{6 haloalkyl,} C 1 -C ₆ ^{haloalkylthio,} optionally substituted by ^{R 3a} _(C 1 -C _{6) alkylthio,} C 1 -C ₆ haloalkylsulfinyl or Represents C ₁ -C ₆ haloalkylsulfonyl,
R ⁴ is a hydrogen atom, a halogen _atom, C 1 -C _{6 haloalkyl,} C 1 -C ₆ ^{haloalkylthio,} optionally substituted by ^{R 4a} _(C 1 -C _{6) alkylthio,} C 1 -C ₆ haloalkylsulfinyl or Represents C ₁ -C ₆ haloalkylsulfonyl,
A ^1a is the fused heterocyclic compound or a salt thereof according to [2], which represents a hydrogen atom or C ₁ -C ₆ alkyl, or an N-oxide thereof.

[6]
A ⁴ represents C(R ⁴ ),
A ⁵ represents a nitrogen atom,
R ² represents a hydrogen atom,
R ⁴ represents a hydrogen atom or C ₁ -C ₆ haloalkyl,
Y1 represents a hydrogen atom, C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
Y2 is a hydrogen atom, a halogen _atom, C 1 -C _{6 alkyl,} C 1 -C _{6 haloalkyl,} C 2 -C ₆ alkenyl, optionally substituted by ^{Y b} _(C 2 -C ₆₎ alkynyl, _{C 1} - C _{8 alkoxy,} C 1 -C _{6 alkylthio,} C 1 -C ₆ haloalkylthio, optionally substituted by ^{Y a} _(C 1 -C _{6) alkylthio,} C 1 -C _{6 alkylsulfinyl,} C 1 -C ₆ alkyl represents _sulphonyl, -NH 2, ^{-NHR 90 g,} nitro, cyano, phenyl, phenyl optionally substituted by ^{Y c,} thiophen-2-yl, pyridin-3-yl or pyridin-4-yl,
Y3 is hydrogen atom, halogen _atom, C 1 -C _{6 alkyl,} C 1 -C _{6 haloalkyl,} C 2 -C ₆ alkenyl, optionally substituted by ^{Y b} _(C 2 -C ₆₎ alkynyl, _{C 1} - C _{8 alkoxy,} C 1 -C ₆ alkylthio, optionally substituted by ^{Y a} _(C 1 -C _{6) alkylthio,} C 1 -C _{6 alkylsulfinyl,} C 1 -C ₆ alkylsulfonyl, -C (O) R ^90a , -C(O)N( ^R90c ) ^R90b , -C(O)OH, cyano or nitro,
Y4 represents a hydrogen atom, a halogen _atom, C 1 -C _{6 alkyl,} C 1 -C _{6 haloalkyl,} C 1 -C _{8 alkoxy,} C 1 -C _{6 alkylthio,} C 1 -C ₆ alkylsulfonyl, -N ^{(R 90h} ) R represents ^{90 g} or cyano,
Y ^a represents C ₁ -C ₈ alkoxycarbonyl,
Y ^b represents phenyl optionally substituted by C ₃ -C ₆ cycloalkyl, trimethylsilyl, C ₁ -C ₈ alkoxy or Y ^b2 ,
Y ^c represents a halogen atom or a _C 1 -C ₆ haloalkyl,
R ^90a represents C ₁ -C ₆ alkyl or C ₁ -C ₈ alkoxy,
R ^90b and R ^90c each independently represent C ₁ -C ₆ alkyl,
R ^90g represents C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkylcarbonyl, C ₁ -C ₈ alkoxycarbonyl or phenylcarbonyl,
R ^90h is the fused heterocyclic compound or salt thereof according to [5], which represents C ₁ -C ₆ alkyl, or their N-oxides.

[7]
A ⁴ represents a nitrogen atom,
A ⁵ represents C(R ⁵ ),
R ² represents a hydrogen atom,
R ³ represents C ₁ -C ₆ haloalkyl,
R ⁵ represents a hydrogen atom or C ₁ -C ₆ alkyl,
Y1 represents a hydrogen atom,
Y2 represents a hydrogen atom, a halogen atom or a _C 1 -C ₆ haloalkyl,
Y3 represents a hydrogen atom, a halogen atom, C ₁ -C ₆ haloalkyl or cyano,
Y4 represents a hydrogen atom, condensed heterocyclic compound or a salt thereof or their N- oxides halogen atom or a C ₁ -C ₈ alkoxy [5], wherein.

[8]
Q represents a ring represented by Q2,
A ⁴ represents a nitrogen atom or C(R ⁴ ),
A ⁵ represents a nitrogen atom or C(R ⁵ ),
(However, the case where both A ⁴ and A ⁵ represent a nitrogen atom is excluded)
R ¹ represents C ₁ -C ₆ alkyl,
R ² represents a hydrogen atom,
R ³ represents a hydrogen atom, a halogen _atom, C 1 -C _{6 haloalkyl,} C 1 -C ₆ ^{haloalkylthio,} optionally substituted by ^{R 3a} _(C 1 -C _{6) alkylthio,} C 1 -C ₆ haloalkylsulfinyl or Represents C ₁ -C ₆ haloalkylsulfonyl,
R ⁴ is a hydrogen atom, a halogen _atom, C 1 -C _{6 haloalkyl,} C 1 -C ₆ ^{haloalkylthio,} optionally substituted by ^{R 4a} _(C 1 -C _{6) alkylthio,} C 1 -C ₆ haloalkylsulfinyl or The fused heterocyclic compound according to [2], which represents C ₁ -C ₆ haloalkylsulfonyl, a salt thereof, or an N-oxide thereof.

[9]
A ⁴ represents a nitrogen atom,
A ⁵ represents C(R ⁵ ),
R ³ represents C ₁ -C ₆ haloalkyl,
R ⁵ represents a hydrogen atom or C ₁ -C ₆ alkyl,
R ⁶ represents a hydrogen atom, a halogen atom or C ₁ -C ₆ alkyl,
Y1 and Y4 represent a hydrogen atom,
Y2 represents a hydrogen atom, a halogen atom or a _C 1 -C ₆ haloalkyl,
Y3 is fused heterocyclic compound or a salt thereof or a N- oxide represents a hydrogen atom or a C ₁ -C ₆ haloalkyl [8].

[10]
Q represents a ring represented by Q3,
A ⁴ represents a nitrogen atom or C(R ⁴ ),
A ⁵ represents a nitrogen atom or C(R ⁵ ),
(However, the case where both A ⁴ and A ⁵ represent a nitrogen atom is excluded)
R ¹ represents C ₁ -C ₆ alkyl,
R ² represents a hydrogen atom,
R ³ represents a hydrogen atom, a halogen _atom, C 1 -C _{6 haloalkyl,} C 1 -C ₆ ^{haloalkylthio,} optionally substituted by ^{R 3a} _(C 1 -C _{6) alkylthio,} C 1 -C ₆ haloalkylsulfinyl or Represents C ₁ -C ₆ haloalkylsulfonyl,
R ⁴ is a hydrogen atom, a halogen _atom, C 1 -C _{6 haloalkyl,} C 1 -C ₆ ^{haloalkylthio,} optionally substituted by ^{R 4a} _(C 1 -C _{6) alkylthio,} C 1 -C ₆ haloalkylsulfinyl or The fused heterocyclic compound according to [2], which represents C ₁ -C ₆ haloalkylsulfonyl, a salt thereof, or an N-oxide thereof.

[11]
A ⁴ represents a nitrogen atom,
A ⁵ represents C(R ⁵ ),
R ³ represents C ₁ -C ₆ haloalkyl,
R ⁵ represents a hydrogen atom,
R ⁶ represents a hydrogen atom,
Y1 represents a hydrogen atom,
Y2 and Y3 each independently represent a hydrogen atom, a halogen atom or C ₁ -C ₆ haloalkyl,
Y4 is a condensed heterocyclic compound or a salt thereof according to [10], which represents a hydrogen atom or a halogen atom, or an N-oxide thereof.

[12]
Q is the fused heterocyclic compound described in [2], which represents the ring represented by Q4, a salt thereof, or an N-oxide thereof.

[13]
R ¹ represents C ₁ -C ₆ alkyl,
R ⁶ represents a hydrogen atom or C ₁ -C ₆ alkyl,
R ⁷ represents C ₁ -C ₆ haloalkyl,
R ⁸ represents a hydrogen atom or C ₁ -C ₆ alkyl,
Y1 and Y4 represent a hydrogen atom,
Y2 represents a hydrogen atom, a halogen atom or a _C 1 -C ₆ haloalkyl,
Y3 is the condensed heterocyclic compound according to [12], a salt thereof, or an N-oxide thereof, which represents a hydrogen atom or C ₁ -C ₆ haloalkyl.

[14]
R ¹ represents C ₁ -C ₆ alkyl,
R ² represents a hydrogen atom,
R ³ represents C ₁ -C ₆ haloalkyl,
R ⁴ represents a hydrogen atom,
A ^1a represents C ₁ -C ₆ alkyl,
Y5 represents a hydrogen atom,
Y6 represents phenyl optionally substituted by halogen _atom, C 1 -C ₆ haloalkyl or ^{Y c,}
Y ^c represents a condensed heterocyclic compound according to [3], which represents C ₁ -C ₆ haloalkyl, a salt thereof, or an N-oxide thereof.

[15]
R ¹ represents C ₁ -C ₆ alkyl,
R ² represents a hydrogen atom,
R ³ represents C ₁ -C ₆ haloalkyl,
R ⁴ represents a hydrogen atom,
A ^1a represents C ₁ -C ₆ alkyl,
T _1a represents C ₁ -C ₆ alkyl,
Y1, Y3 and Y4 represent a hydrogen atom,
Y2 _is, C 1 -C ₆ haloalkyl are presented [4], wherein the fused heterocyclic compound or a salt thereof or their N- oxide.

[16]
A ¹ represents N(A ^1a ), or an oxygen atom,
R ² represents a hydrogen atom,
R ³ represents C ₁ -C ₆ haloalkyl, C ₁ -C ₆ haloalkylthio, C ₁ -C ₆ haloalkylsulfinyl or C ₁ -C ₆ haloalkylsulfonyl,
R ⁴ represents a hydrogen atom,
R ⁵ represents a hydrogen atom or C ₁ -C ₆ alkyl,
R ⁶ represents a hydrogen atom,
A ^1a represents C ₁ -C ₆ alkyl,
Y1 and Y4 represent a hydrogen atom,
Y2 and Y3 are each independently fused heterocyclic compound or a salt thereof or a N- oxide hydrogen atom or a C ₁ -C ₆ represents a haloalkyl [2], wherein.

[17]
A pest control agent containing, as an active ingredient, one kind or two or more kinds selected from the condensed heterocyclic compound and the salt thereof according to any one of [1] to [16].

[18]
An agrochemical containing as an active ingredient one or more selected from the fused heterocyclic compounds and salts thereof according to any one of [1] to [16].

[19]
A control agent for internal or ectoparasites of mammals or birds, which contains, as an active ingredient, one or more selected from the fused heterocyclic compound and the salt thereof according to any one of [1] to [16]. ..

[20]
The control agent according to [19], wherein the ectoparasite is a flea or a tick.

[21]
An insecticide or acaricide containing, as an active ingredient, one kind or two or more kinds selected from the fused heterocyclic compound and the salt thereof according to any one of [1] to [16].

[22]
A seed treatment agent containing, as an active ingredient, one kind or two or more kinds selected from the condensed heterocyclic compound and the salt thereof according to any one of [1] to [16].

[23]
The seed treatment agent according to [22], wherein the seed treatment is performed by immersion treatment.

[24]
A soil treatment agent containing, as an active ingredient, one or more selected from the condensed heterocyclic compounds described in any one of [1] to [16].

[25]
The soil treatment agent according to [24], wherein the soil treatment is performed by soil irrigation treatment.

The compound of the present invention has excellent insecticidal and acaricidal activity against many agricultural pests, spider mites, mammals or birds internal or ectoparasites, and to pests that have acquired resistance to existing insecticides. It also exerts a sufficient control effect. Furthermore, it has almost no adverse effect on mammals, fish, and beneficial insects, has low persistence, and has a low environmental load. Therefore, the present invention can provide a useful novel pest control agent.

The compound included in the present invention may have geometrical isomers of E-form and Z-form depending on the kind of the substituent, but the present invention includes these E-form, Z-form or E-form. And a mixture containing Z-form in an arbitrary ratio.

Further, the compound included in the present invention has an optically active substance due to the presence of one or more asymmetric carbon atoms or asymmetric sulfur atoms, but the present invention includes all optically active substances or racemic compounds. Including the body.

Further, the compound included in the present invention may have tautomers depending on the kind of the substituents, but the present invention includes all tautomers or a mixture of tautomers in any proportion. Is included.

Of the compounds included in the present invention, those which can be converted into salts by a conventional method include, for example, hydrofluoric acid, hydrochloric acid, hydrobromic acid, hydroiodic acid and other hydrohalic acid salts, Inorganic acid salts such as nitric acid, sulfuric acid, phosphoric acid, chloric acid and perchloric acid, methanesulfonic acid, ethanesulfonic acid, trifluoromethanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid and other sulfonic acid salts, formic acid, Acetic acid, propionic acid, trifluoroacetic acid, fumaric acid, tartaric acid, oxalic acid, maleic acid, malic acid, succinic acid, benzoic acid, mandelic acid, ascorbic acid, lactic acid, gluconic acid, carboxylic acid salts such as citric acid, glutamic acid, Amino acid salts such as aspartic acid, alkali metal salts such as lithium, sodium and potassium, alkaline earth metal salts such as calcium, barium and magnesium, aluminum salts, tetramethylammonium salt, tetrabutylammonium salt, benzyltrimethylammonium salt And the like.

In the compound of the present invention, N-oxide is a compound in which a nitrogen atom constituting a ring on a heterocyclic group is oxidized. Examples of the heterocyclic group capable of forming an N-oxide include a condensed ring containing a pyridine ring, a condensed ring containing a pyrazine ring, a condensed ring containing a pyridazine ring and a condensed ring containing a pyrimidine ring.

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

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

The expression "C _a -C _b alkyl" in the present specification represents a linear or branched hydrocarbon group having a carbon number of ab, for example, methyl group, ethyl group, n-propyl group. Specific examples include a group, i-propyl group, n-butyl group, i-butyl group, s-butyl group, tert-butyl group, n-pentyl group, 1,1-dimethylpropyl group and n-hexyl group. Selected within each specified number of carbon atoms.

In the present specification, the expression "C _a -C _b haloalkyl" refers to a linear or branched chain having from _a to _b carbon atoms, in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom. When the hydrocarbon group is substituted with 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, 1-fluoroethyl 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, 2-bromo-2,2-difluoroethyl group, 1,1,2,2-tetrafluoroethyl group, 2-chloro-1,1,2-trifluoroethyl group, 2-chloro-1 ,1,2,2-Tetrafluoroethyl group, pentafluoroethyl group, 2,2-difluoropropyl group, 3,3,3-trifluoropropyl group, 3-bromo-3,3-difluoropropyl group, 2, 2,3,3-tetrafluoropropyl group, 2,2,3,3,3-pentafluoropropyl group, 1,1,2,3,3,3-hexafluoropropyl group, heptafluoropropyl group, 2, 2,2-trifluoro-1-(methyl)ethyl group, 2,2,2-trifluoro-1-(trifluoromethyl)ethyl group, 1,2,2,2-tetrafluoro-1-(trifluoro Methyl) ethyl group, 2,2,3,4,4,4-hexafluorobutyl group, 2,2,3,3,4,4,4-heptafluorobutyl group, nonafluorobutyl group etc. And selected within each specified number of carbon atoms.

In the present specification, the expression "C _a -C _b alkenyl" refers to a linear or branched chain having a carbon atoms of _a to _b , and having 1 or 2 or more double bonds in the molecule. Represents an unsaturated hydrocarbon group having, 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 mentioned as specific examples, and each is selected within the specified number of carbon atoms.

In the present specification, the expression "C _a -C _b haloalkenyl" refers to a linear or branched chain having a carbon atoms of ab in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom. It represents a chain-like unsaturated hydrocarbon group having one or more double bonds in the molecule. At this time, when it is substituted with two or more halogen atoms, those halogen atoms may be the same 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 group -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 thereof include a trifluoro-2-butenyl group and the like, and each is selected within the specified carbon atom number range.

Notation "C _a -C _b alkynyl" in the present specification have a straight or branched chain carbon atoms is from a~b pieces, and one in the molecule, or two or more triple bonds It represents an unsaturated hydrocarbon group, for example, an ethynyl group, a propargyl group, a 2-butynyl group, a 3-butynyl group, a 1-pentynyl group, a 1-hexynyl group, a 4,4,4-trifluoro-2-butynyl group and the like. Specific examples are given, and each is selected in the range of the specified number of carbon atoms.

In the present specification, the expression "C _a -C _b haloalkynyl" refers to a linear or branched chain having a carbon number of ab, in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom. It represents a chain-like unsaturated hydrocarbon group having one or two or more triple bonds in the molecule. At this time, when it is substituted with two or more halogen atoms, those halogen atoms may be the same or different from each other. Specific examples include a 2-chloroethynyl group, a 2-bromoethynyl group, a 2-iodoethynyl group, a 3-chloro-2-propynyl group, a 3-bromo-2-propynyl group, and a 3-iodo-2-propynyl group. And selected within each specified number of carbon atoms.

In the present specification, the notation "C _a -C _b cycloalkyl" represents a cyclic hydrocarbon group having a carbon atoms of ab, and represents a monocyclic or composite ring structure having from 3 to 6 membered rings. Can be formed. Further, each ring may be optionally substituted with an alkyl group within the specified number of carbon atoms. Specific examples thereof include a cyclopropyl group, a 1-methylcyclopropyl group, a 2-methylcyclopropyl group, a 2,2-dimethylcyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and the like. Selected in a range of numbers.

In the present specification, the expression "C _a -C _b halocycloalkyl" means a cyclic hydrocarbon having a carbon number of ab, in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom. It represents a group and can form a monocyclic or composite ring structure having from 3 to 6 membered rings. In addition, each ring may be optionally substituted with an alkyl group within a specified number of carbon atoms, and the substitution with a halogen atom may be a ring structure portion, a side chain portion, or Both may be present, and when 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 thereof include a cyclopropyl group, a 2,2-dibromo-1-methylcyclopropyl group, a 2,2,3,3-tetrafluorocyclobutyl group, etc., each of which is selected within the specified number of carbon atoms. It

The expression "C _a -C _b alkoxy" in the present specification represents an alkyl-O- group having the above-mentioned meaning in which the number of carbon atoms is _{a- b} , for example, methoxy group, ethoxy group, n-propyloxy group. Group, i-propyloxy group, n-butyloxy group, i-butyloxy group, s-butyloxy group, tert-butyloxy group, 2-ethylhexyloxy group and the like are mentioned as specific examples, each of which has a specified number of carbon atoms. Selected by range.

The notation of "C _a -C _b haloalkoxy" in the present specification represents a haloalkyl-O- group having the above-mentioned meaning in which the number of carbon atoms is ab, for example, difluoromethoxy group, trifluoromethoxy group, Chlorodifluoromethoxy group, bromodifluoromethoxy group, 2-fluoroethoxy group, 2-chloroethoxy group, 2,2,2-trifluoroethoxy group, 1,1,2,2-tetrafluoroethoxy group, 2-chloro Specific examples thereof include a -1,1,2-trifluoroethoxy group and a 1,1,2,3,3,3-hexafluoropropyloxy group, which are selected within the specified carbon atom number range. ..

The expression "C _a -C _b alkenyloxy" in the present specification represents an alkenyl-O- group having the above-mentioned meaning in which the number of carbon atoms is ab, for example, 2-propenyloxy group, 2- Specific examples thereof include butenyloxy group, 2-methyl-2-propenyloxy group, 3-methyl-2-butenyloxy group, etc., and each is selected within the specified carbon atom number range.

The expression "C _a -C _b haloalkenyloxy" in the present specification represents a haloalkenyl-O- group having the above-mentioned meaning and having a carbon number of ab, for example, 3,3-difluoroallyl. Specific examples thereof include an oxy group and a 3,3-dichloroallyloxy group, and each is selected within the specified carbon atom number range.

Notation "C _a -C _b alkynyloxy" in the present specification represents an alkynyl -O- group is meant the number of carbon atoms is from a~b number, for example, an ethynyl group, propargyloxy group, Specific examples thereof include a 2-butynyloxy group, a 1-pentynyloxy group, a 1-hexynyloxy group, etc., and each is selected within the specified number of carbon atoms.

Notation "C _a -C _b haloalkynyloxy" in the present specification represents a haloalkynyl -O- group is meant the number of carbon atoms is from a~b number, for example, 3-chloro-2- Specific examples thereof include a propynyloxy group, a 3-bromo-2-propynyloxy group, a 3-iodo-2-propynyloxy group and the like, and each is selected within the specified carbon atom number range.

The expression "C _a -C _b alkylthio" in the present specification represents an alkyl-S- group having the above-mentioned meaning in which the number of carbon atoms is ab, for example, methylthio group, ethylthio group, n-propylthio group. , I-propylthio group, n-butylthio group, i-butylthio group, s-butylthio group, tert-butylthio group and the like are mentioned as specific examples, and each is selected within the specified carbon atom number range.

The expression "C _a -C _b haloalkylthio" in the present specification represents a haloalkyl-S- group having the above-mentioned meaning in which the number of carbon atoms is ab, for example, difluoromethylthio group, trifluoromethylthio group, Chlorodifluoromethylthio group, bromodifluoromethylthio group, 2,2,2-trifluoroethylthio group, 1,1,2,2-tetrafluoroethylthio group, 2-chloro-1,1,2-trifluoroethylthio group Group, pentafluoroethylthio group, 1,1,2,3,3,3-hexafluoropropylthio group, heptafluoropropylthio group, 1,2,2,2-tetrafluoro-1-(trifluoromethyl) Specific examples thereof include an ethylthio group and a nonafluorobutylthio group, each of which is selected within the specified carbon atom number range.

The expression "C _a -C _b alkenylthio" in the present specification represents an alkenyl-S- group having the above-mentioned meaning in which the number of carbon atoms is ab, for example, 2-propenylthio group, 2- Specific examples thereof include butenylthio group, 2-methyl-2-propenylthio group, 3-methyl-2-butenylthio group, etc., and each is selected within the specified carbon atom number range.

The expression "C _a -C _b haloalkenylthio" in the present specification represents a haloalkenyl-S- group having the above-mentioned meaning and having a carbon number of ab, for example, 2-fluoro-2-. Propenylthio group, 2-chloro-2-propenylthio group, 3,3-difluoro-2-propenylthio group, 3,3-dichloro-2-propenylthio group, 2,3,3-trifluoro-2-propenyl A thio group, a 4,4-difluoro-3-butenylthio group, a 3,4,4-trifluoro-3-butenylthio group and the like are mentioned as specific examples, and each is selected within the range of the designated carbon atom number.

Notation "C _a -C _b alkynylthio" in the present specification represents an alkynyl -S- group is meant the number of carbon atoms is from a~b number, for example, propynylthio group, butynylthio group, pentynylthio Groups, hexynylthio groups and the like are mentioned as specific examples, and each is selected within the specified number of carbon atoms.

The expression "C _a -C _b haloalkynylthio" in the present specification represents a haloalkynyl-S- group having the above-mentioned meaning and having a carbon number of ab, for example, 3-chloro-2-. Specific examples thereof include a propynylthio group, a 3-bromo-2-propynylthio group, a 3-iodo-2-propynylthio group and the like, and each is selected within the specified carbon atom number range.

Notation "C _a -C _b alkylsulfinyl" in the present specification, alkyl -S is meant the number of carbon atoms is from a~b pieces (O) - group, for example, methylsulfinyl group, ethylsulfinyl Group, n-propylsulfinyl group, i-propylsulfinyl group, n-butylsulfinyl group, i-butylsulfinyl group, s-butylsulfinyl group, tert-butylsulfinyl group and the like are mentioned as specific examples, and carbons designated by each It is selected in the range of the number of atoms.

Notation "C _a -C _b haloalkylsulfinyl" in the present specification, a haloalkyl -S carbon atoms is as defined above consisting a~b pieces (O) - group, for example, difluoromethyl sulfinyl group, tri Fluoromethylsulfinyl group, chlorodifluoromethylsulfinyl group, bromodifluoromethylsulfinyl group, 2,2,2-trifluoroethylsulfinyl group, 1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethylsulfinyl group , Nonafluorobutylsulfinyl group, etc. are mentioned as specific examples, and each is selected within the specified number of carbon atoms.

The expression "C _a -C _b alkenylsulfinyl" in the present specification represents an alkenyl-S(O)- group having the above-mentioned meaning in which the number of carbon atoms is ab, for example, 2-propenyl. Sulfinyl group, 2-butenylsulfinyl group, 2-methyl-2-propenylsulfinyl group, 3-methyl-2-butenylsulfinyl group and the like are mentioned as specific examples, and within the range of the number of carbon atoms specified for each. To be selected.

The expression "C _a -C _b haloalkenylsulfinyl" in the present specification represents a haloalkenyl-S(O)- group having the above-mentioned meaning and having a carbon number of ab, for example, 2-fluoro. -2-propenylsulfinyl group, 2-chloro-2-propenylsulfinyl group, 3,3-difluoro-2-propenylsulfinyl group, 3,3-dichloro-2-propenylsulfinyl group, 4,4-difluoro-3-bu Specific examples thereof include a tenylsulfinyl group and a 3,4,4-trifluoro-3-butenylsulfinyl group, each of which is selected within the specified number of carbon atoms.

The expression "C _a -C _b alkynylsulfinyl" in the present specification represents an alkynyl-S(O)- group having the above-mentioned meaning in which the number of carbon atoms is ab, for example, 2-propynylsulfinyl group. , 2-butynylsulfinyl group and the like are mentioned as specific examples, and each is selected within the specified number of carbon atoms.

The expression "C _a -C _b haloalkynylsulfinyl" in the present specification represents a haloalkynyl-S(O)- group having the above-mentioned meaning and having a carbon number of ab, for example, 3-chloro. -2-propynylsulfinyl group, 3-bromo-2-propynylsulfinyl group, 3-iodo-2-propynylsulfinyl group and the like are mentioned as specific examples, and each is selected within the specified number of carbon atoms.

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

Notation "C _a -C _b haloalkylsulfonyl" in the present specification, haloalkyl -SO 2 the meaning of the number of carbon atoms is from a~b pieces _- group, for example, difluoromethyl sulfonyl group, trifluoromethyl Sulfonyl group, chlorodifluoromethylsulfonyl group, bromodifluoromethylsulfonyl group, 2,2,2-trifluoroethylsulfonyl group, 1,1,2,2-tetrafluoroethylsulfonyl group, 2-chloro-1,1,2 -Trifluoroethyl sulfonyl group etc. are mentioned as a specific example, It is selected in the range of each designated carbon atom.

The expression "C _a -C _b alkenylsulfonyl" in the present specification represents an alkenyl-SO ₂ -group having the above-mentioned meaning in which the number of carbon atoms is ab, for example, 2-propenylsulfonyl group. , 2-butenylsulfonyl group, 2-methyl-2-propenylsulfonyl group, 3-methyl-2-butenylsulfonyl group and the like are listed as specific examples, and each is selected within the range of the number of designated carbon atoms. It

The expression "C _a -C _b haloalkenylsulfonyl" in the present specification represents a haloalkenyl-SO ₂ -group having the above-mentioned meaning and having a carbon number of ab, for example, 2-fluoro-2. -Propenylsulfonyl group, 2-chloro-2-propenylsulfonyl group, 3,3-difluoro-2-propenylsulfonyl group, 3,3-dichloro-2-propenylsulfonyl group, 4,4-difluoro-3-butenylsulfonyl group Group, 3,4,4-trifluoro-3-butenylsulfonyl group, etc. are mentioned as specific examples, and each is selected within the specified carbon atom number range.

Notation "C _a -C _b alkynyl sulfonyl" herein, alkynyl -SO ₂ the meaning of the number of carbon atoms is from a~b pieces - group, for example, 2-propynyl sulfonyl group, 2 -Butynylsulfonyl group and the like are mentioned as a specific example, and each is selected within the range of the designated carbon atom number.

Notation "C _a -C _b haloalkynyl sulfonyl" herein, haloalkynyl -SO ₂ the meaning of the number of carbon atoms is from a~b pieces - group, for example, 3-chloro-2 Specific examples thereof include -propynylsulfonyl group, 3-bromo-2-propynylsulfonyl group, 3-iodo-2-propynylsulfonyl group, etc., each of which is selected within the specified number of carbon atoms.

The expression "C _a -C _b alkylamino" in the present specification represents an amino group in which one of the hydrogen atoms is substituted by an alkyl group having the above-mentioned meaning in which the number of carbon atoms is ab, for example, Specific examples include methylamino group, ethylamino group, n-propylamino group, i-propylamino group, n-butylamino group, i-butylamino group, tert-butylamino group, and the like. It is selected in the range of the number of atoms.

The expression "C _a -C _b haloalkylamino" in the present specification represents an amino group in which one of the hydrogen atoms is substituted by a haloalkyl group having the above-mentioned meaning in which the number of carbon atoms is ab, for example, Specific examples include 2,2,2-trifluoroethylamino group, 2-chloro-2,2-difluoroethylamino group, and 3,3,3-trifluoropropylamino group, each designated carbon atom. Selected in a range of numbers.

In the present specification, the expression "di(C _a -C _b )alkylamino" has the above-mentioned meaning in which both hydrogen atoms may be the same or different from each other, and the number of carbon atoms 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 Specific examples thereof include a -propyl)amino group and a di(n-butyl)amino group, and each is selected within the specified carbon atom number range.

In the present specification, the expression "di(C _a -C _b )haloalkylamino" has the above-mentioned meaning in which both hydrogen atoms may be the same or different from each other and have _a to _b carbon atoms. Which represents an amino group substituted by a haloalkyl group, which is, for example, a bis(2,2,2-trifluoroethyl)amino group and the like, and is selected within the range of the number of designated carbon atoms. ..

Notation "C _a -C _b alkylcarbonyl" in the present specification, alkyl -C (O) is defined above the number of carbon atoms is from a~b pieces - group, for example, an acetyl group, a propionyl group , Butyryl group, isobutyryl group, valeryl group, isovaleryl group, 2-methylbutanoyl group, pivaloyl group, hexanoyl group, heptanoyl group and the like are mentioned as specific examples, and each is selected within the range of the designated carbon atom number.

Notation "C _a -C _b haloalkylcarbonyl" in the present specification, a haloalkyl -C is meant the number of carbon atoms is from a~b pieces (O) - group, for example, trifluoroacetyl group, chloro Acetyl group, difluoroacetyl group, dichloroacetyl group, trifluoroacetyl group, chlorodifluoroacetyl group, bromodifluoroacetyl group, trichloroacetyl group, pentafluoropropionyl group, heptafluorobutanoyl group, 3-chloro-2,2-dimethyl Specific examples thereof include a propanoyl group and the like, and each is selected within the range of the designated number of carbon atoms.

The expression "C _a -C _b alkoxycarbonyl" in the present specification represents an alkyl-O-C(O)- group having the above-mentioned meaning in which the number of carbon atoms is ab, such as a methoxycarbonyl group. Ethoxycarbonyl group, n-propyloxycarbonyl group, i-propyloxycarbonyl group, n-butoxycarbonyl group, i-butoxycarbonyl group, s-butoxycarbonyl group, tert-butoxycarbonyl group, 2-ethylhexyloxycarbonyl group Etc. are mentioned as a specific example, and each is selected within the specified number of carbon atoms.

Notation "C _a -C _b haloalkoxycarbonyl" in the present specification, haloalkyl -O-C is defined above the number of carbon atoms is from a~b pieces (O) - group, for example, chloromethoxy Specific examples include a carbonyl group, a 2-chloroethoxycarbonyl group, a 2,2-difluoroethoxycarbonyl group, a 2,2,2,-trifluoroethoxycarbonyl group, and a 2,2,2,-trichloroethoxycarbonyl group. , Selected within the specified number of carbon atoms.

The expression "C _a -C _b alkylaminocarbonyl" in the present specification represents a carbamoyl group in which one of hydrogen atoms is substituted by an alkyl group having the above-mentioned meaning in which the number of carbon atoms is ab, for example, Specific examples include a methylcarbamoyl group, an ethylcarbamoyl group, an n-propylcarbamoyl group, an i-propylcarbamoyl group, an n-butylcarbamoyl group, an i-butylcarbamoyl group, an s-butylcarbamoyl group, and a tert-butylcarbamoyl group. Selected within the specified number of carbon atoms.

The expression "C _a -C _b haloalkylaminocarbonyl" in the present specification represents a carbamoyl group in which one of hydrogen atoms is substituted with a haloalkyl group having the above-mentioned meaning and having a carbon number of ab, for example, Specific examples include 2-fluoroethylcarbamoyl group, 2-chloroethylcarbamoyl group, 2,2-difluoroethylcarbamoyl group, 2-trifluoroethylcarbamoyl group, etc., each selected within the specified number of carbon atoms. It

In the present specification, the expression "C _a -C _b alkylaminothiocarbonyl" refers to an alkylamino-C(=S)- group in which one of the hydrogen atoms has the above-mentioned meaning in which the number of carbon atoms is ab. For example, methylthiocarbamoyl group, ethylthiocarbamoyl group, n-propylthiocarbamoyl group, i-propylthiocarbamoyl group, n-butylthiocarbamoyl group, i-butylthiocarbamoyl group, s-butylthiocarbamoyl group, tert- A butylthiocarbamoyl group and the like can be mentioned as a specific example, and each is selected within the specified number of carbon atoms.

The expression "C _a -C _b haloalkylaminothiocarbonyl" in the present specification refers to a haloalkylamino-C(=S)- group in which one of the hydrogen atoms has the above-mentioned meaning in which the number of carbon atoms is ab. Examples include 2-fluoroethylthiocarbamoyl group, 2-chloroethylthiocarbamoyl group, 2,2-difluoroethylthiocarbamoyl group, 2-trifluoroethylthiocarbamoyl group, etc. It is selected within the range of the number of carbon atoms.

The expression "C _a -C _b alkylaminosulfonyl" in the present specification represents a sulfamoyl group in which one of hydrogen atoms is substituted with an alkyl group having the above-mentioned meaning in which the number of carbon atoms is ab, for example, , Methylsulfamoyl group, ethylsulfamoyl group, n-propylsulfamoyl group, i-propylsulfamoyl group, n-butylsulfamoyl group, i-butylsulfamoyl group, s-butylsulfamoyl group Specific examples thereof include a moyl group and a tert-butylsulfamoyl group, and each is selected within the specified carbon atom number range.

In the present specification, the expression "di(C _a -C _b )alkylaminosulfonyl" means that both hydrogen atoms may be the same or different from each other, and the number of carbon atoms is a to b. Represents a sulfamoyl group substituted by an alkyl group having the meaning, for example, N,N-dimethylsulfamoyl group, N-ethyl-N-methylsulfamoyl group, N,N-diethylsulfamoyl group, N, Specific examples include an N-di(n-propyl)sulfamoyl group and an N,N-di(n-butyl)sulfamoyl group, which are selected within the specified carbon atom number range.

The expression "heterocyclic group" in the present specification is, for example, thiophen-2-yl, thiophen-3-yl, furan-2-yl, furan-3-yl, pyrrol-1-yl, pyrrol. -2-yl, pyrrol-3-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl. Il, isoxazolin-3-yl, isoxazolin-4-yl, isoxazolin-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazole -4-yl, isothiazol-5-yl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1-yl, imidazol-2-yl, Imidazol-4-yl, 1,3,4-oxadiazol-2-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-i, 1, 3,4-thiadiazol-2-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,2,4-triazol-1-yl, 1,2, 4-triazol-3-yl, 1,2,4-triazol-5-yl, 1,2,3-thiadiazol-4-yl, 1,2,3-thiadiazol-5-yl, 1,2,3- Triazol-1-yl, 1,2,3-triazol-2-yl, 1,2,3-triazol-4-yl, 1,2,3,4-tetrazol-1-yl, 1,2,3 4-tetrazol-2-yl, 1,2,3,4-tetrazol-5-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyrimidin-2-yl, pyrimidine-4- Yl, pyrimidin-5-yl, pyrazin-2-yl, pyridazin-3-yl, pyridazin-4-yl, 1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl, 1,2,4-triazin-5-yl, 1,2,4-triazin-6-yl, benzothiophen-2-yl, benzothiophen-3-yl, benzothiophen-4-yl, benzothiophen-5-yl Yl, benzothiophen-6-yl, benzothiophen-7-yl, benzofuran-2-yl, benzofuran-3-yl, benzofuran-4-yl, benzofuran-5-yl, benzofuran-6-yl, benzofuran -7-yl, indol-1-yl, indol-2-yl, indol-3-yl, indol-4-yl, indol-5-yl, indol-6-yl, indol-7-yl, benzothiazol- 2-yl, benzothiazol-4-yl, benzothiazol-5-yl, benzothiazol-6-yl, benzothiazol-7-yl, benzimidazol-1-yl, benzimidazol-2-yl, benzimidazole-4 -Yl, benzimidazol-5-yl, benzimidazol-6-yl, benzimidazol-7-yl, benzisoxazol-3-yl, benzisoxazol-4-yl, benzisoxazol-5-yl, benziso Oxazol-6-yl, benzisoxazol-7-yl, benzisothiazol-3-yl, benzisothiazol-4-yl, benzisothiazol-5-yl, benzisothiazol-6-yl, benzisothiazol-yl 7-yl, indazol-1-yl, indazol-3-yl, indazol-4-yl, indazol-5-yl, indazol-6-yl, indazol-7-yl, benzoxazol-2-yl, benzoxazol- 4-yl, benzoxazol-5-yl, benzoxazol-6-yl, benzoxazol-7-yl, quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinoline -6-yl, quinolin-7-yl, quinolin-8-yl, isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7. -Yl, isoquinolin-8-yl, quinoxalin-2-yl, quinoxalin-3-yl, quinoxalin-5-yl, quinoxalin-6-yl, quinoxalin-7-yl, quinoxalin-8-yl, phthalazin-1-yl , Phthalazin-4-yl, phthalazin-5-yl, phthalazin-6-yl, phthalazin-7-yl, phthalazin-8-yl, cinnoline-3-yl, cinnoline-4-yl, cinnoline-5-yl, cinnoline -6-yl, cinnolin-7-yl, cinnolin-8-yl, quinazolin-2-yl, quinazolin-4-yl, quinazolin-5-yl, quinazolin-6-yl, quinazolin-7-yl or quinazolin-8. -Ill and the like are mentioned as specific examples.

In the present specification, "C _a -C _b cycloalkyl (C _d -C _e )alkyl", "C _a -C _b halocycloalkyl (C _d -C _e )alkyl" or "hydroxy (C _d -C _e )" The notation such as "alkyl" and the like means that a hydrogen atom bonded to a carbon atom is optionally substituted by any C _{a to} C _b cycloalkyl group, C _{a to} C _b halocycloalkyl group, or hydroxyl group, each of which has the above meaning. It represents an alkyl group having the number of carbon atoms of d to e, which has the above-mentioned meaning, and is selected within the range of the specified number of carbon atoms.

In the present specification, (C _a -C _b )alkyl optionally substituted with R ^1a , a (C ₁ -C ₆ )alkyl group optionally substituted with A ^1a-a , optionally substituted with Y ^a ( C ₁ -C ₆₎ notation such as an alkyl group, any ^{R 1a,} by ^{a 1a-a} or ^{Y a,} consisting a~b number carbon atoms bonded to hydrogen atoms are optionally substituted carbon atoms It represents an alkyl group having the above meaning, and is selected in the range of the number of carbon atoms specified in each. At this time, when there are two or more substituents R ^1a , A ^1a-a or Y ^a on each (C _{a to} C _b )alkyl group, each R ^1a , A ^1a-a or Y ^a is mutually different. It may be the same or different.

In the present specification, the notation such as (C _a -C _b )haloalkyl optionally substituted by A ^{1 a-a} , (C _a -C _b )haloalkyl optionally substituted by Y ^a, means any A ^1a-a. Or Y ^a represents a haloalkyl group having the above-mentioned meaning in which the number of carbon atoms optionally substituted by a hydrogen atom or a halogen atom bonded to a carbon atom is ^{a to b} , and the range of the number of carbon atoms in each designation is represented. Selected by. At this time, when there are two or more substituents A ^1a-a or Y ^a on each (C _a -C _b )haloalkyl group, each A ^1a-a or Y ^a may be the same or different. ..

Notation such as _(C a ~C _b) alkenyl optionally substituted by Y ^a herein, by any Y ^a, the number of carbon atoms bonded hydrogen atom is optionally substituted carbon atoms a~ It represents an alkenyl group of the above meaning consisting of b and is selected within the specified number of carbon atoms. At this time, when there are two or more substituents Y ^a on each (C _a -C _b )alkenyl group, each Y ^a may be the same or different.

In the present specification, the notation such as (C _{a to} C _b )alkynyl optionally substituted by Y ^b indicates that the number of carbon atoms in which a hydrogen atom bonded to a carbon atom is optionally substituted by any Y ^b is a to It represents an alkynyl group of the above meaning consisting of b and is selected within the respective specified number of carbon atoms. At this time, when there are two or more substituents Y ^b on each (C _a -C _b )alkynyl group, each Y ^b may be the same or different.

Notation such as _(C a ~C _b) alkoxy optionally substituted by Y ^a herein, by any Y ^a, the number of carbon atoms bonded hydrogen atom is optionally substituted carbon atoms a~ It represents an alkoxy group of the above meaning consisting of b and is selected within the specified number of carbon atoms. At this time, when there are two or more substituents Y ^a on each (C _a -C _b )alkoxy group, each Y ^a may be the same or different.

Optionally substituted by Y ^a herein (C a _{-C b)} representation of an alkenyloxy by any Y ^a, the number of carbon atoms bonded hydrogen atom is optionally substituted carbon atom a ~b represents an alkenyloxy group having the above-mentioned meaning and is selected within the specified number of carbon atoms. At this time, when there are two or more substituents Y ^a on each (C _a -C _b )alkenyloxy group, each Y ^a may be the same or different.

Optionally substituted by Y ^a herein (C a _{-C b)} notation alkynyloxy, etc., by any Y ^a, the number of carbon atoms bonded hydrogen atom is optionally substituted carbon atom a ~b represents an alkynyloxy group having the above-mentioned meaning and is selected within the specified number of carbon atoms. At this time, when there are two or more substituents Y ^a on each (C _a -C _b )alkynyloxy group, each Y ^a may be the same or different.

Optionally substituted by ^{R 3a} in this specification _(C a _{~C b)} ^alkylthio, optionally substituted by ^{R 4a} _(C ^a _{~C b)} alkylthio, optionally substituted by ^{Y a} _(C ^a ~ C _b) notation alkylthio, etc., any R ^3a, by R ^4a or Y ^a, which is the meaning of the number of carbon atoms in which the hydrogen atoms bonded to carbon atom is optionally substituted is more a~b number alkylthio Represents a group and is selected within each specified number of carbon atoms. At this time, when there are two or more substituents R ^3a , R ^4a or Y ^a on each (C _{a to} C _b )alkylthio group, each R ^3a , R ^4a or Y ^a may be the same or different. Good.

Optionally substituted by Y ^a herein (C a _{-C b)} representation of such alkylsulfinyl by any Y ^a, the number of carbon atoms bonded hydrogen atom is optionally substituted carbon atom a ~b represents an alkylsulfinyl group having the above-mentioned meaning and is selected within the specified number of carbon atoms. At this time, when there are two or more substituents Y ^a on each (C _a -C _b )alkylsulfinyl group, each Y ^a may be the same or different.

Optionally substituted by Y ^a herein (C a _{-C b)} notation such as alkylsulfonyl, by any Y ^a, the number of carbon atoms bonded hydrogen atom is optionally substituted carbon atom a ~b represents an alkylsulfonyl group having the above-mentioned meaning and selected in the specified number of carbon atoms. At this time, when there are two or more substituents Y ^a on each (C _a -C _b )alkylsulfonyl group, each Y ^a may be the same or different.

Phenyl optionally substituted by R ^3b herein, notation phenyl group optionally substituted by phenyl or Y ^c optionally substituted by R ^4b are any R ^3b, by R ^4b or Y ^c , Represents a phenyl group in which a hydrogen atom bonded to a carbon atom is optionally substituted. At this time, when there are two or more substituents R ^3b , R ^4b or Y ^c on each phenyl group, each R ^3b , R ^4b or Y ^c may be the same or different.

Heterocyclic ring optionally substituted by R ^3b herein, the notation of heterocycles optionally substituted by heterocycle or Y ^c optionally substituted by R ^4b are any R ^3b, R ^4b, or Y ^c represents a heterocyclic group in which a hydrogen atom bonded to a carbon atom or a nitrogen atom is optionally substituted. At this time, when there are two or more substituents R ^3b , R ^4b or Y ^c on each heterocyclic group, each R ^3b , R ^4b or Y ^c may be the same or different.

Next, a method for producing the compound of the present invention represented by the formula (1) will be described below. The compound of the present invention can be produced, for example, by the following production methods 1 to 17.

Manufacturing method 1

A compound represented by the formula (2Q1-a) (in the formula, A ^1a , A ² , A ³ , A ⁴ and A ⁵ have the same meanings as described above), and a compound represented by the formula (3D-a) (in the formula, R ¹ , D and n have the same meanings as described above.) By reacting the compound represented by the formula (1) in a solvent or without a solvent, optionally in the presence of a dehydration condensing agent, and optionally in the presence of a catalyst, 4-a) (wherein R ¹ , A ^1a , A ² , A ³ , A ⁴ , A ⁵ , D and n have the same meanings as described above) can be produced. When a solvent is used, the solvent used may be inert to the reaction, and examples thereof include lower alcohols such as water, methanol and ethanol, diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane and the like. Aromatic hydrocarbons such as ethers, benzene, chlorobenzene, bromolobenzene, xylene and toluene, aliphatic hydrocarbons such as pentane, hexane and cyclohexane, halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane , Nitriles such as acetonitrile and propionitrile, amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, N,N'-dimethylimidazolidinone, and sulfoxides such as dimethylsulfoxide And nitrogen-containing aromatic compounds such as pyridine and quinoline, and mixed solvents thereof.

The reaction can be carried out in the presence of a dehydration condensation agent. Examples of the dehydrating condensing agent that can be used include 1H-benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate, N,N′-dicyclohexylcarbodiimide, 1-ethyl-3-(3-dimethylamino). Propyl)carbodiimide hydrochloride and 2-chloro-1-methylpyridinium iodide. The equivalent of the dehydration condensing agent can be used in the range of 0.1 to 100 equivalent based on the compound represented by the formula (2Q1-a), and preferably in the range of 1 to 20 equivalent.

The reaction can be carried out in the presence of a catalyst. Examples of the catalyst that can be used include 1-hydroxybenzotriazole and 4-(dimethylamino)pyridine. The equivalent of the catalyst can be used in the range of 0.005 to 20 equivalents relative to the compound represented by the formula (2Q1-a), preferably 0.1 to 5 equivalents.

The reaction temperature can be set at any temperature from −80° C. to the reflux temperature of the reaction mixture, and the range of 0° C. to the reflux temperature of the reaction mixture is preferable.

Although the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, it can usually be arbitrarily set within the range of 5 minutes to 100 hours, and preferably within the range of 1 hour to 48 hours.

As the equivalent of the substrate, the compound (3D-a) can be used in the range of 0.5 to 50 equivalents, and preferably the range of 1 to 20 equivalents, relative to the compound (2Q1-a).

The compound represented by the formula (4-a) includes a compound represented by the formula (2Q1-a) and a compound represented by the formula (3D-b) (in the formula, R ¹ , D and n have the same meanings as described above). .) can be produced by reacting the compound represented by the formula (1) in a solvent or without a solvent in the presence of a base in some cases. When a solvent is used, the solvent used may be inert to the reaction, and examples thereof include lower alcohols such as water, methanol and ethanol, diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane and the like. Aromatic hydrocarbons such as ethers, benzene, chlorobenzene, bromolobenzene, xylene and toluene, aliphatic hydrocarbons such as pentane, hexane and cyclohexane, halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane , Nitriles such as acetonitrile and propionitrile, amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, N,N'-dimethylimidazolidinone, and sulfoxides such as dimethylsulfoxide And nitrogen-containing aromatic compounds such as pyridine and quinoline, and mixed solvents thereof.

The reaction can be carried out in the presence of a base. Examples of the base that can be used include pyridine, 2,6-lutidine, 4-dimethylaminopyridine, triethylamine, diisopropylethylamine, tributylamine, 4-(dimethylamino)pyridine, 1,4-diazabicyclo[2.2.2]. ] Organic bases such as octane (DABCO), 1,8-diazabicyclo[5.4.0]-7-undecene (DBU) or 1,5-diazabicyclo[4.3.0]-5-nonene (DBN) Inorganic bases such as sodium hydroxide, potassium hydroxide, sodium hydride, sodium hydrogen carbonate, potassium carbonate and cesium carbonate. The equivalent of the base can be used in the range of 0.1 to 100 equivalents based on the compound represented by the formula (2Q1-a), and preferably 1 to 20 equivalents.

The reaction temperature can be set at any temperature from −80° C. to the reflux temperature of the reaction mixture, and the range of 0° C. to the reflux temperature of the reaction mixture is preferable.

Although the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, it can usually be arbitrarily set within the range of 5 minutes to 100 hours, and preferably within the range of 1 hour to 48 hours.

As the equivalent of the substrate, the compound (3D-b) can be used in the range of 0.5 to 50 equivalents, preferably the range of 1 to 20 equivalents, relative to the compound (2Q1-a).

Then, the compound represented by the formula (4-a) is subjected to dehydration condensation in a solvent or without a solvent, optionally in the presence of an acid, and optionally in the presence of a dehydrating agent to give a compound of the formula (1-a) (formula In the above, compounds represented by R ¹ , A ^1a , A ² , A ³ , A ⁴ , A ⁵ , D and n have the same meanings as described above. When a solvent is used, the solvent used may be inert to the reaction, and examples thereof include lower alcohols such as water, methanol and ethanol, diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane and the like. Aromatic hydrocarbons such as ethers, benzene, chlorobenzene, bromolobenzene, xylene and toluene, aliphatic hydrocarbons such as pentane, hexane and cyclohexane, halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane , Nitriles such as acetonitrile and propionitrile, amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, N,N'-dimethylimidazolidinone, and sulfoxides such as dimethylsulfoxide And nitrogen-containing aromatic compounds such as pyridine and quinoline, and mixed solvents thereof.

The reaction can be carried out in the presence of acid. Examples of the acid that can be used include paratoluenesulfonic acid, polyphosphoric acid, acetic acid, and propionic acid. The equivalent amount of the acid can be used in the range of 0.1 to 1000 equivalents, preferably 1 to 500 equivalents, relative to the compound represented by formula (4-a).

The reaction can be carried out in the presence of a dehydrating agent. Dehydrating agents that can be used include phosphorus oxychloride and acetic anhydride. The equivalent of the dehydrating agent can be used in the range of 0.5 to 50 equivalents with respect to the compound represented by the formula (4-a), and is preferably in the range of 1 to 20 equivalents.

The reaction temperature can be set at any temperature from −80° C. to the reflux temperature of the reaction mixture, and the range of 0° C. to the reflux temperature of the reaction mixture is preferable.

Although the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, it can usually be arbitrarily set within the range of 5 minutes to 100 hours, and preferably within the range of 1 hour to 48 hours.

Some of the compounds represented by the general formula (2Q1-a) are known compounds, and some of them are commercially available. Also, other compounds can be synthesized, for example, according to the following reaction formula 4.

The compound represented by the formula (3D-a) can be synthesized, for example, according to the following reaction formulas 1 and 2.

The compound represented by the formula (3D-b) can be synthesized, for example, according to the reaction formula 1 described below.

Manufacturing method 2

A compound represented by the formula (1-f) (wherein R ¹ , A ² , A ³ , A ⁴ , A ⁵ , D and n have the same meanings as described above); In the above, A ^1aa represents a C ₁ -C ₆ alkyl group, X ₁ represents a halogen atom, a C ₁ -C ₄ alkylsulfonate group (eg, methanesulfonyloxy group, etc.), a C ₁ -C ₄ haloalkylsulfonate group (eg, And a leaving group such as a trifluoromethanesulfonyloxy group) or an arylsulfonate group (eg, benzenesulfonyloxy group, p-toluenesulfonyloxy group, etc.). ] The compound represented by Formula (1-g) (In formula, R ^{< 1 >} , A ^<1aa> , A ^{< 2 >} , A ^{< 3 >} , A ^{< 4} > is made to react by reacting the compound represented by these in a solvent or absence of solvent depending on the case. , A ⁵ , D and n have the same meanings as described above.) can be produced. When a solvent is used, the solvent used may be inert to the reaction, and examples thereof include lower alcohols such as water, methanol and ethanol, diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane and the like. Aromatic hydrocarbons such as ethers, benzene, chlorobenzene, bromolobenzene, xylene and toluene, aliphatic hydrocarbons such as pentane, hexane and cyclohexane, halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane , Nitriles such as acetonitrile and propionitrile, amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, N,N'-dimethylimidazolidinone, and sulfoxides such as dimethylsulfoxide And nitrogen-containing aromatic compounds such as pyridine and quinoline, and mixed solvents thereof.

The reaction can be carried out in the presence of a base. Examples of the base that can be used include pyridine, 2,6-lutidine, 4-dimethylaminopyridine, triethylamine, diisopropylethylamine, tributylamine, 4-(dimethylamino)pyridine, 1,4-diazabicyclo[2.2.2]. ] Organic bases such as octane (DABCO), 1,8-diazabicyclo[5.4.0]-7-undecene (DBU) or 1,5-diazabicyclo[4.3.0]-5-nonene (DBN) Inorganic bases such as sodium hydroxide, potassium hydroxide, sodium hydride, sodium hydrogen carbonate, potassium carbonate and cesium carbonate. The equivalent of the base can be used in the range of 0.1 to 100 equivalent based on the compound represented by the formula (1-f), and preferably 1 to 20 equivalent.

The reaction temperature can be set at any temperature from −80° C. to the reflux temperature of the reaction mixture, and the range of 0° C. to the reflux temperature of the reaction mixture is preferable.

Although the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, it can usually be arbitrarily set within the range of 5 minutes to 100 hours, and preferably within the range of 1 hour to 48 hours.

As the equivalent of the substrate, the compound (16) can be used in the range of 0.5 to 50 equivalents relative to the compound (1-f), and preferably in the range of 1 to 20 equivalents.

The compound represented by the general formula (1-f) can be synthesized according to the production method 1.

Some of the compounds represented by formula (16) are known compounds, and some of them are commercially available.

Manufacturing method 3

A compound represented by the formula (2Q1-a) and a compound represented by the formula (17-a) (wherein G ₁ , G ₂ , G ₃ and G ₄ have the same meanings as described above), By reacting according to the method described in the step [A] of production method 1, the compound represented by the formula (18-a) (in the formula, A ^1a , A ² , A ³ , A ⁴ , A ⁵ , G ₁ , G _{2 is used).} , G ₃ and G ₄ have the same meanings as described above.) can be produced.

In addition, the compound represented by the formula (18-a) includes a compound represented by the formula (2Q1-a) and a compound represented by the formula (17-b) (wherein G ₁ , G ₂ , G ₃ and G ₄ are the same as those described above). A compound represented by the formula (1) is reacted according to the method described in the step [A] of the production method 1.

Then, the compound represented by the formula (18-a) is dehydrated and condensed according to the method described in the step [B] of the production method 1 to give the compound of the formula (19-a) (in the formula, A ^1a , A ^{1 2} , A ³ , A ⁴ , A ⁵ , G ₁ , G ₂ , G ₃ and G ₄ have the same meanings as described above.) can be produced.

Then, the compound represented by the formula (19-a), in a solvent or without a solvent, represented by the formula (9) (in the formula, R ¹ has the same meaning as described above) and a halogenating agent. By reacting with formula (1-h) (wherein R ¹ , A ^1a , A ² , A ³ , A ⁴ , A ⁵ , G ₁ , G ₂ , G _3, and G ₄ have the same meanings as described above. A compound represented by the formula (1) can be produced. When a solvent is used, the solvent used may be inert to the reaction, and examples thereof include lower alcohols such as water, methanol and ethanol, diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane and the like. Aromatic hydrocarbons such as ethers, benzene, chlorobenzene, bromolobenzene, xylene and toluene, aliphatic hydrocarbons such as pentane, hexane and cyclohexane, halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane , Nitriles such as acetonitrile and propionitrile, amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, N,N'-dimethylimidazolidinone, and sulfoxides such as dimethylsulfoxide And nitrogen-containing aromatic compounds such as pyridine and quinoline, and mixed solvents thereof.

As the halogenating agent, chlorine, bromine, iodine, N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, 1,3-dichloro-5,5-dimethylhydantoin, 1,3-dibromo-5,5- Examples thereof include dimethylhydantoin and 1,3-diiodo-5,5-dimethylhydantoin. The equivalent of the halogenating agent can be used in the range of 0.5 to 50 equivalents relative to the compound represented by formula (19-a), and is preferably in the range of 1 to 20 equivalents.

The reaction temperature can be set at any temperature from −80° C. to the reflux temperature of the reaction mixture, and the range of 0° C. to the reflux temperature of the reaction mixture is preferable.

Although the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, it can usually be arbitrarily set within the range of 5 minutes to 100 hours, and preferably within the range of 1 hour to 48 hours.

As the equivalent of the substrate, the compound (9) can be used in the range of 0.5 to 50 equivalents with respect to the compound (19-a), and the range of 1 to 20 equivalents is preferable.

Further, by reacting the compound represented by the formula (19-a) with a halogenating agent in a solvent or without a solvent, the compound represented by the formula (23-a) (in the formula, A ^1a , A ² , A ³ , _{^{a 4, a 5, G 1}} , G 2, G 3 and _{G 4} are as defined _{above, X 10} is able to produce chlorine atom, bromine atom or iodine atom.) and a compound represented by it can. When a solvent is used, the solvent used may be inert to the reaction, and examples thereof include lower alcohols such as water, methanol and ethanol, diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane and the like. Aromatic hydrocarbons such as ethers, benzene, chlorobenzene, bromolobenzene, xylene and toluene, aliphatic hydrocarbons such as pentane, hexane and cyclohexane, halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane , Nitriles such as acetonitrile and propionitrile, amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, N,N'-dimethylimidazolidinone, and sulfoxides such as dimethylsulfoxide And nitrogen-containing aromatic compounds such as pyridine and quinoline, and mixed solvents thereof.

As the halogenating agent, chlorine, bromine, iodine, N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, 1,3-dichloro-5,5-dimethylhydantoin, 1,3-dibromo-5,5- Examples thereof include dimethylhydantoin and 1,3-diiodo-5,5-dimethylhydantoin. The equivalent of the halogenating agent can be used in the range of 0.5 to 50 equivalents relative to the compound represented by formula (19-a), and is preferably in the range of 1 to 20 equivalents.

The reaction temperature can be set at any temperature from −80° C. to the reflux temperature of the reaction mixture, and the range of 0° C. to the reflux temperature of the reaction mixture is preferable.

Although the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, it can usually be arbitrarily set within the range of 5 minutes to 100 hours, and preferably within the range of 1 hour to 48 hours.

Then, the compound represented by the formula (23-a) and the compound represented by the formula (24) (in the formula, R ¹ has the same meaning as described above) in a solvent or without a solvent, depending on the case. By reacting in the presence of a base, the formula (1-h) (in the formula, R ¹ , A ^1a , A ² , A ³ , A ⁴ , A ⁵ , G ₁ , G ₂ , G _3, and G ₄ are the same as those described above). A compound represented by the same meaning) can be produced. When a solvent is used, the solvent used may be inert to the reaction, and examples thereof include lower alcohols such as water, methanol and ethanol, diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane and the like. Aromatic hydrocarbons such as ethers, benzene, chlorobenzene, bromolobenzene, xylene and toluene, aliphatic hydrocarbons such as pentane, hexane and cyclohexane, halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane , Nitriles such as acetonitrile and propionitrile, amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, N,N'-dimethylimidazolidinone, and sulfoxides such as dimethylsulfoxide And nitrogen-containing aromatic compounds such as pyridine and quinoline, and mixed solvents thereof.

The reaction can be carried out in the presence of a base. Examples of the base that can be used include pyridine, 2,6-lutidine, 4-dimethylaminopyridine, triethylamine, diisopropylethylamine, tributylamine, 4-(dimethylamino)pyridine, 1,4-diazabicyclo[2.2.2]. ] Organic bases such as octane (DABCO), 1,8-diazabicyclo[5.4.0]-7-undecene (DBU) or 1,5-diazabicyclo[4.3.0]-5-nonene (DBN) Inorganic bases such as sodium hydroxide, potassium hydroxide, sodium hydride, sodium hydrogen carbonate, potassium carbonate and cesium carbonate. The equivalent of the base can be used in the range of 0.1 to 100 equivalent based on the compound represented by the formula (23-a), and preferably 1 to 20 equivalent.

The reaction temperature can be set at any temperature from −80° C. to the reflux temperature of the reaction mixture, and the range of 0° C. to the reflux temperature of the reaction mixture is preferable.

Although the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, it can usually be arbitrarily set within the range of 5 minutes to 100 hours, and preferably within the range of 1 hour to 48 hours.

As the equivalent of the substrate, the compound (24) can be used in the range of 0.5 to 50 equivalents, preferably the range of 1 to 20 equivalents, relative to the compound (23-a).

In addition, the compound represented by the formula (1-h) is a compound represented by the formula (23-a) and a compound represented by the formula (9) in a solvent or without a solvent, and in some cases, a base is present. In some cases, the reaction can be carried out in the presence of a palladium catalyst and, in some cases, in the presence of a ligand. When a solvent is used, the solvent used may be inert to the reaction, and examples thereof include water, lower alcohols such as methanol and ethanol, diethyl ether, tetrahydrofuran, 1,4-dioxane, and 1,2-dimethoxyethane. Aromatic hydrocarbons such as ethers, benzene, chlorobenzene, bromolobenzene, xylene and toluene, aliphatic hydrocarbons such as pentane, hexane and cyclohexane, halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane , Nitriles such as acetonitrile and propionitrile, amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, N,N'-dimethylimidazolidinone, and sulfoxides such as dimethylsulfoxide And nitrogen-containing aromatic compounds such as pyridine and quinoline, and mixed solvents thereof.

The reaction can be carried out in the presence of a base. Examples of the base that can be used include pyridine, 2,6-lutidine, 4-dimethylaminopyridine, triethylamine, diisopropylethylamine, tributylamine, 4-(dimethylamino)pyridine, 1,4-diazabicyclo[2.2.2]. ] Organic bases such as octane (DABCO), 1,8-diazabicyclo[5.4.0]-7-undecene (DBU) or 1,5-diazabicyclo[4.3.0]-5-nonene (DBN) Inorganic bases such as sodium hydroxide, potassium hydroxide, sodium hydride, sodium hydrogen carbonate, potassium carbonate and cesium carbonate. The equivalent of the base can be used in the range of 0.1 to 100 equivalent based on the compound represented by the formula (23-a), and preferably 1 to 20 equivalent.

The reaction can be carried out in the presence of a palladium catalyst. Examples of the palladium catalyst that can be used include palladium-carbon, palladium(II) chloride, palladium(II) acetate, bis(triphenylphosphine)palladium(II) dichloride, tetrakis(triphenylphosphine)palladium(0), and bis(triphenylphosphine)palladium(0). (Dibenzylideneacetone)palladium (0), tris(dibenzylideneacetone)dipalladium (0) and the like can be mentioned. The equivalent of the palladium catalyst can be used in the range of 0.005 to 20 equivalents, and preferably the range of 0.01 to 5 equivalents relative to compound (23-a).

The reaction can be carried out in the presence of a ligand. Examples of the ligand that can be used include 4,5'-bis(diphenylphosphino)-9,9'-dimethylxanthene and 1,10-phenanthroline. The equivalent amount of the ligand can be used in the range of 0.005 to 20 equivalents, and preferably the range of 0.01 to 5 equivalents, relative to compound (23-a).

The reaction temperature can be set at any temperature from −80° C. to the reflux temperature of the reaction mixture, and the range of 0° C. to the reflux temperature of the reaction mixture is preferable.

Although the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, it can usually be arbitrarily set within the range of 5 minutes to 100 hours, and preferably within the range of 1 hour to 48 hours.

As the equivalent of the substrate, the compound (9) can be used in the range of 0.5 to 50 equivalents relative to the compound (23-a), and preferably in the range of 1 to 20 equivalents.

Some of the compounds represented by formula (17-a) are known compounds, and some of them are commercially available.

Some of the compounds represented by formula (17-b) are known compounds, and some of them are commercially available.

Some of the compounds represented by formula (9) are known compounds, and some of them are commercially available.

Some of the compounds represented by formula (24) are known compounds, and some of them are commercially available.

Manufacturing method 4

The compound represented by the formula (2Q1-a) is represented by the formula (20-a) (in the formula, T ₁ , G ₁ , G ₂ , G ₃ and G ₄ have the same meanings as described above). By reacting the compound with a compound according to the method described in the step [A] of the production method 1, the compound of the formula (21-a) (in the formula, A ^1a , A ² , A ³ , A ⁴ , A ⁵ , and T ₁ ) is reacted. , G ₁ , G ₂ , G ₃ and G ₄ have the same meanings as described above.) can be produced.

Further, the compound represented by the formula (21-a) includes a compound represented by the formula (2Q1-a) and a compound represented by the formula (20-b) (in the formula, T ₁ , G ₁ , G ₂ , G ₃ and G). ₄ has the same meaning as described above.), and can be produced by reacting according to the method described in the step [A] of production method 1.

Then, the compound represented by the formula (21-a) is dehydrated and condensed according to the method described in the step [B] of the production method 1 to give the compound of the formula (22-a) (in the formula, A ^1a , A ^{1 2} , A ³ , A ⁴ , A ⁵ , T ₁ , G ₁ , G ₂ , G _3, and G ₄ have the same meanings as described above.) can be produced.

Then, the compound represented by the formula (22-a) is reacted according to the method described in Step [C] of Production Method 3 or the method described in Step [D] and Step [E] of Production Method 3. By doing so, formula (1-i) (wherein R ¹ , A ^1a , A ² , A ³ , A ⁴ , A ⁵ , T ₁ , G ₁ , G ₂ , G _3, and G ₄ are the same as above. A compound represented by the meaning) can be produced.

Some of the compounds represented by formula (20-a) are known compounds, and some of them are commercially available.

Some of the compounds represented by formula (20-b) are known compounds, and some of them are commercially available.

Manufacturing method 5

The compound represented by the formula (2Q1-b) (in the formula, A ² , A ³ , A ⁴ and A ⁵ have the same meanings as described above, and A ^1b represents an oxygen atom or a sulfur atom) is a compound represented by the formula (2Q1-b): By reacting the compound represented by 3D-a) according to the method described in the step [A] of production method 1, formula (4-b) (in the formula, A ^1b , R ¹ , A ² , A ³ , A ⁴ , A ⁵ , D and n have the same meanings as described above.) can be produced.

In addition, the compound represented by the formula (4-b) includes the compound represented by the formula (2Q1-b) and the compound represented by the formula (3D-b) in the step [A] of the production method 1. It can also be produced by reacting according to the method described.

Then, by reacting the compound represented by the formula (4-b) in a solvent or without a solvent, optionally in the presence of an acid, and optionally in the presence of a dehydration condensation agent, the compound of the formula (1-b) (in the formula: , A ^1b , R ¹ , A ² , A ³ , A ⁴ , A ⁵ , D and n have the same meanings as described above.) can be produced. When a solvent is used, the solvent used may be inert to the reaction, and examples thereof include lower alcohols such as water, methanol and ethanol, diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane and the like. Aromatic hydrocarbons such as ethers, benzene, chlorobenzene, bromolobenzene, xylene and toluene, aliphatic hydrocarbons such as pentane, hexane and cyclohexane, halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane , Nitriles such as acetonitrile and propionitrile, amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, N,N'-dimethylimidazolidinone, and sulfoxides such as dimethylsulfoxide And nitrogen-containing aromatic compounds such as pyridine and quinoline, and mixed solvents thereof.

The reaction can be carried out in the presence of acid. Examples of the acid that can be used include paratoluenesulfonic acid, polyphosphoric acid, acetic acid, and propionic acid. The equivalent amount of the acid can be used in the range of 0.1 to 1000 equivalents, preferably 1 to 500 equivalents, relative to the compound represented by the formula (4-b).

The reaction can be carried out in the presence of a dehydration condensation agent. Examples of the dehydrating condensing agent that can be used include a mixture of triphenylphosphine and bis(2-methoxyethyl)azodicarboxylate.

The equivalent of triphenylphosphine can be used in the range of 0.5 to 50 equivalents relative to the compound represented by formula (4-b), and is preferably in the range of 1 to 20 equivalents.

The equivalent of bis(2-methoxyethyl)azodicarboxylate can be used in the range of 0.5 to 50 equivalents, and the range of 1 to 20 equivalents, relative to the compound represented by formula (4-b). preferable.

The reaction temperature can be set at any temperature from −80° C. to the reflux temperature of the reaction mixture, and the range of 0° C. to the reflux temperature of the reaction mixture is preferable.

Although the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, it can usually be arbitrarily set within the range of 5 minutes to 100 hours, and preferably within the range of 1 hour to 48 hours.

Some of the compounds represented by formula (2Q1-b) are known compounds, and some of them are commercially available.

Manufacturing method 6

A compound represented by the formula (2Q2-a) (wherein A ² , A ³ , A ⁴ and A ⁵ have the same meanings as described above); and a compound represented by the formula (3D-c) (in the formula, R ¹ , R ⁶ , D and n have the same meanings as described above, and X ₂ represents a chlorine atom, a bromine atom or an iodine atom.) in a solvent or without a solvent, and in some cases, reacted in the presence of a base. Thus, a compound represented by the formula (1-c) (in the formula, R ¹ , R ⁶ , A ² , A ³ , A ⁴ , A ⁵ , D and n have the same meanings as described above) is produced. can do. When a solvent is used, the solvent used may be inert to the reaction, and examples thereof include lower alcohols such as water, methanol and ethanol, diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane and the like. Aromatic hydrocarbons such as ethers, benzene, chlorobenzene, bromolobenzene, xylene and toluene, aliphatic hydrocarbons such as pentane, hexane and cyclohexane, halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane , Nitriles such as acetonitrile and propionitrile, amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, N,N'-dimethylimidazolidinone, and sulfoxides such as dimethylsulfoxide And nitrogen-containing aromatic compounds such as pyridine and quinoline, and mixed solvents thereof.

The reaction can be carried out in the presence of a base. Examples of the base that can be used include pyridine, 2,6-lutidine, 4-dimethylaminopyridine, triethylamine, diisopropylethylamine, tributylamine, 4-(dimethylamino)pyridine, 1,4-diazabicyclo[2.2.2]. ] Organic bases such as octane (DABCO), 1,8-diazabicyclo[5.4.0]-7-undecene (DBU) or 1,5-diazabicyclo[4.3.0]-5-nonene (DBN) Inorganic bases such as sodium hydroxide, potassium hydroxide, sodium hydride, sodium hydrogen carbonate, potassium carbonate and cesium carbonate. The equivalent of the base can be used in the range of 0.1 to 100 equivalents based on the compound represented by the formula (2Q2-a), and preferably 1 to 20 equivalents.

The reaction temperature can be set at any temperature from −80° C. to the reflux temperature of the reaction mixture, and the range of 0° C. to the reflux temperature of the reaction mixture is preferable.

Although the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, it can usually be arbitrarily set within the range of 5 minutes to 100 hours, and preferably within the range of 1 hour to 48 hours.

Some of the compounds represented by formula (2Q2-a) are known compounds, and some of them are commercially available. Other compounds can also be synthesized, for example, according to the reaction formula 5 described below.

The compound represented by the formula (3D-c) can be synthesized, for example, according to the reaction formula 1 described below.

Manufacturing method 7

A compound represented by formula (1-j) (wherein R ¹ , A ² , A ³ , A ⁴ , A ⁵ , D and n have the same meanings as described above), a halogenating agent, and a solvent. By reacting in the medium or without solvent, the formula (1-k) (in the formula, R ¹ , A ² , A ³ , A ⁴ , A ⁵ , D and n have the same meanings as described above, and X ₄ is chlorine. An atom, a bromine atom or an iodine atom) can be produced. When a solvent is used, the solvent used may be inert to the reaction, and examples thereof include lower alcohols such as water, methanol and ethanol, diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane and the like. Aromatic hydrocarbons such as ethers, benzene, chlorobenzene, bromolobenzene, xylene and toluene, aliphatic hydrocarbons such as pentane, hexane and cyclohexane, halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane , Nitriles such as acetonitrile and propionitrile, amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, N,N'-dimethylimidazolidinone, and sulfoxides such as dimethylsulfoxide And nitrogen-containing aromatic compounds such as pyridine and quinoline, and mixed solvents thereof.

As the halogenating agent, chlorine, bromine, iodine, N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, 1,3-dichloro-5,5-dimethylhydantoin, 1,3-dibromo-5,5- Examples thereof include dimethylhydantoin and 1,3-diiodo-5,5-dimethylhydantoin. The equivalent of the halogenating agent can be used in the range of 0.5 to 50 equivalents, preferably 1 to 20 equivalents, relative to the compound represented by formula (1-j).

The reaction temperature can be set at any temperature from −80° C. to the reflux temperature of the reaction mixture, and the range of 0° C. to the reflux temperature of the reaction mixture is preferable.

Although the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, it can usually be arbitrarily set within the range of 5 minutes to 100 hours, and preferably within the range of 1 hour to 48 hours.

The compound represented by the formula (1-j) can be synthesized according to the method described in Production method 6.

Manufacturing method 8

A compound represented by the formula (2Q3-a) (in the formula, R ² , R ³ , A ⁴ and A ⁵ have the same meanings as described above), and a compound represented by the formula (3D-d) (in the formula, R ¹ , D and n have the same meanings as described above. By reacting the compound represented by the formula (40) (in the formula, R ¹ and R ² ) in a solvent or in the absence of a solvent, optionally in the presence of an acid. , R ³ , A ⁴ , A ⁵ , D and n have the same meanings as described above.) can be produced. When a solvent is used, the solvent used may be inert to the reaction, and examples thereof include lower alcohols such as water, methanol and ethanol, diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane and the like. Aromatic hydrocarbons such as ethers, benzene, chlorobenzene, bromolobenzene, xylene and toluene, aliphatic hydrocarbons such as pentane, hexane and cyclohexane, halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane , Nitriles such as acetonitrile and propionitrile, amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, N,N'-dimethylimidazolidinone, and sulfoxides such as dimethylsulfoxide And nitrogen-containing aromatic compounds such as pyridine and quinoline, and mixed solvents thereof.

The reaction can be carried out in the presence of acid. Examples of the acid that can be used include acetic acid, formic acid, and paratoluenesulfonic acid. The acid equivalent can be used in the range of 0.1 to 100 equivalent based on the compound represented by the formula (2Q3-a), and preferably in the range of 1 to 20 equivalent.

The reaction temperature can be set at any temperature from −80° C. to the reflux temperature of the reaction mixture, and the range of 0° C. to the reflux temperature of the reaction mixture is preferable.

Although the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, it can usually be arbitrarily set within the range of 5 minutes to 100 hours, and preferably within the range of 1 hour to 48 hours.

As the equivalent of the substrate, the compound (3D-d) can be used in the range of 0.5 to 50 equivalents, preferably the range of 1 to 20 equivalents, relative to the compound (2Q3-a).

Then, by reacting the compound represented by the formula (40) with a phosphite ester in a solvent or without a solvent, the compound represented by the formula (1-1) (in the formula, R ¹ , R ² , R ³ , and A) is reacted. ⁴ , A ⁵ , D and n have the same meanings as described above.) can be produced. When a solvent is used, the solvent used may be inert to the reaction, and examples thereof include lower alcohols such as water, methanol and ethanol, diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane and the like. Aromatic hydrocarbons such as ethers, benzene, chlorobenzene, bromolobenzene, xylene and toluene, aliphatic hydrocarbons such as pentane, hexane and cyclohexane, halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane , Nitriles such as acetonitrile and propionitrile, amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, N,N'-dimethylimidazolidinone, and sulfoxides such as dimethylsulfoxide And nitrogen-containing aromatic compounds such as pyridine and quinoline, and mixed solvents thereof.

Examples of the phosphite ester include trimethyl phosphite and triethyl phosphite. The equivalent of the phosphite can be used in the range of 0.5 to 50 equivalents based on the compound represented by the formula (40), and is preferably in the range of 1 to 20 equivalents.

The reaction temperature can be set at any temperature from −80° C. to the reflux temperature of the reaction mixture, and the range of 0° C. to the reflux temperature of the reaction mixture is preferable.

Although the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, it can usually be arbitrarily set within the range of 5 minutes to 100 hours, and preferably within the range of 1 hour to 48 hours.

Some of the compounds represented by formula (2Q3-a) are known compounds, and some of them are commercially available. Other methods are also described in publicly known methods described in the literature, for example, Journal of Medicinal Chemistry [J. Med. Chem.] 2008, 50, 2468, International Publication No. 2011/075628. It can be synthesized from a known compound according to the reaction conditions.

Some of the compounds represented by formula (3D-d) are known compounds, and some of them are commercially available. Also, other compounds can be synthesized, for example, according to the reaction formula 6 described below.

Manufacturing method 9

Formula (2Q3-b) (in the formula, R ² , R ³ , A ⁴ and A ⁵ have the same meanings as described above, and X ₃ represents a fluorine atom, a chlorine atom, a bromine atom or an iodine atom). The compound of formula (2Q3-c) (wherein R ² , R ³ , A ⁴ and A ⁵ have the same meanings as described above) by reacting the compound with sodium azide in a solvent or without solvent. A compound represented by can be produced. When a solvent is used, the solvent used may be inert to the reaction, and examples thereof include lower alcohols such as water, methanol and ethanol, diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane and the like. Aromatic hydrocarbons such as ethers, benzene, chlorobenzene, bromolobenzene, xylene and toluene, aliphatic hydrocarbons such as pentane, hexane and cyclohexane, halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane , Nitriles such as acetonitrile and propionitrile, amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, N,N'-dimethylimidazolidinone, and sulfoxides such as dimethylsulfoxide And nitrogen-containing aromatic compounds such as pyridine and quinoline, and mixed solvents thereof.

The reaction temperature can be set at any temperature from −80° C. to the reflux temperature of the reaction mixture, and the range of 0° C. to the reflux temperature of the reaction mixture is preferable.

Although the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, it can usually be arbitrarily set within the range of 5 minutes to 100 hours, and preferably within the range of 1 hour to 48 hours.

As the equivalent of the substrate, sodium azide can be used in the range of 0.5 to 50 equivalents relative to compound (2Q3-b), and the range of 1 to 20 equivalents is preferable.

Then, the compound represented by the formula (2Q3-c) and the compound represented by the formula (3D-d) are reacted in a solvent or without a solvent, optionally in the presence of a base, and optionally in the presence of a catalyst. Thus, the compound represented by the formula (41) (in the formula, R ¹ , R ² , R ³ , A ⁴ , A ⁵ , D and n have the same meanings as described above) can be produced. When a solvent is used, the solvent used may be inert to the reaction, and examples thereof include lower alcohols such as water, methanol and ethanol, diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane and the like. Aromatic hydrocarbons such as ethers, benzene, chlorobenzene, bromolobenzene, xylene and toluene, aliphatic hydrocarbons such as pentane, hexane and cyclohexane, halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane , Nitriles such as acetonitrile and propionitrile, amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, N,N'-dimethylimidazolidinone, and sulfoxides such as dimethylsulfoxide And nitrogen-containing aromatic compounds such as pyridine and quinoline, and mixed solvents thereof.

The reaction can be carried out in the presence of a base. Examples of the base that can be used include pyridine, 2,6-lutidine, 4-dimethylaminopyridine, triethylamine, diisopropylethylamine, tributylamine, 4-(dimethylamino)pyridine, 1,4-diazabicyclo[2.2.2]. ] Organic bases such as octane (DABCO), 1,8-diazabicyclo[5.4.0]-7-undecene (DBU) or 1,5-diazabicyclo[4.3.0]-5-nonene (DBN) Inorganic bases such as sodium hydroxide, potassium hydroxide, sodium hydride, sodium hydrogen carbonate, potassium carbonate and cesium carbonate. The equivalent of the base can be used in the range of 0.1 to 100 equivalents based on the compound represented by the formula (2Q3-c), and preferably 1 to 20 equivalents.

The reaction can be carried out in the presence of a catalyst. Examples of the catalyst that can be used include titanium tetrachloride. The equivalent of the catalyst can be used in the range of 0.005 to 20 equivalents relative to the compound represented by the formula (2Q3-c), and preferably 0.1 to 5 equivalents.

The reaction temperature can be set at any temperature from −80° C. to the reflux temperature of the reaction mixture, and the range of 0° C. to the reflux temperature of the reaction mixture is preferable.

Although the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, it can usually be arbitrarily set within the range of 5 minutes to 100 hours, and preferably within the range of 1 hour to 48 hours.

As the equivalent of the substrate, the compound (3D-d) can be used in the range of 0.5 to 50 equivalents, preferably the range of 1 to 20 equivalents, relative to the compound (2Q3-c).

Then, by cyclizing the compound represented by the formula (41) in a solvent or without a solvent, the compound represented by the formula (1-m) (in the formula, R ¹ , R ² , R ³ , A ⁴ , A ⁵ , D and n have the same meanings as described above.) can be produced.

When a solvent is used, the solvent used may be inert to the reaction, and examples thereof include water, lower alcohols such as methanol and ethanol, diethyl ether, tetrahydrofuran, 1,4-dioxane, and 1,2-dimethoxyethane. Aromatic hydrocarbons such as ethers, benzene, chlorobenzene, bromolobenzene, xylene and toluene, aliphatic hydrocarbons such as pentane, hexane and cyclohexane, halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane , Nitriles such as acetonitrile and propionitrile, amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, N,N'-dimethylimidazolidinone, and sulfoxides such as dimethylsulfoxide And nitrogen-containing aromatic compounds such as pyridine and quinoline, and mixed solvents thereof.

The reaction temperature can be set at any temperature from −80° C. to the reflux temperature of the reaction mixture, and the range of 0° C. to the reflux temperature of the reaction mixture is preferable.

Although the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, it can usually be arbitrarily set within the range of 5 minutes to 100 hours, and preferably within the range of 1 hour to 48 hours.

Some of the compounds represented by the general formula (2Q3-b) are known compounds, and some of them are commercially available. Other compounds can also be synthesized, for example, according to the reaction formula 7 described below.

Manufacturing method 10

The compound of the formula (2Q4-a) (wherein R ⁷ and A ⁸ have the same meanings as described above), the compound of the formula (3D-c), and the production method 6. A compound represented by the formula (1-n) (wherein R ¹ , R ⁶ , R ⁷ , A ⁸ , D and n have the same meanings as described above) is produced by reacting according to the method. can do.

Some of the compounds represented by formula (2Q4-a) are known compounds, and some of them are commercially available. Other than the above, known methods described in the literature, for example, according to the reaction conditions described in Journal of Fluorine Chemistry 2012, 133, 115, CN101768135, CN10188708, etc., are known. It can be synthesized from a compound.

Manufacturing method 11

A compound represented by the formula (1-d) (wherein R ¹ , Q, and D have the same meanings as described above) and an oxidizing agent in a solvent or without a solvent, and in the presence of a catalyst in some cases. By reacting, a compound represented by the formula (1-e) (wherein R ¹ , Q and D have the same meanings as described above, and n′ represents an integer of 1 or 2). You can When a solvent is used, the solvent used may be inert to the reaction, and examples thereof include water, lower alcohols such as methanol and ethanol, diethyl ether, tetrahydrofuran, 1,4-dioxane, and 1,2-dimethoxyethane. Aromatic hydrocarbons such as ethers, benzene, chlorobenzene, bromolobenzene, xylene and toluene, aliphatic hydrocarbons such as pentane, hexane and cyclohexane, halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane , Nitriles such as acetonitrile and propionitrile, amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, N,N'-dimethylimidazolidinone, and sulfoxides such as dimethylsulfoxide And nitrogen-containing aromatic compounds such as pyridine and quinoline, acetic acid or a mixed solvent thereof and the like.

Examples of the oxidizing agent include peracids such as metachloroperbenzoic acid and peracetic acid, hydrogen peroxide, and oxone (OXONE, registered trademark of E. I. DuPont; potassium peroxodisulfate-containing material). The equivalent of the oxidizing agent can be used in the range of 0.1 to 100 equivalent based on the compound represented by the formula (1-d), and is preferably in the range of 1 to 20 equivalent.

The reaction can be carried out in the presence of a catalyst. Examples of the catalyst that can be used include sodium tungstate. The equivalent of the catalyst can be used in the range of 0.005 to 20 equivalents relative to the compound represented by the formula (1-d), preferably 0.1 to 5 equivalents.

The reaction temperature can be set at any temperature from −80° C. to the reflux temperature of the reaction mixture, and the range of 0° C. to the reflux temperature of the reaction mixture is preferable.

Although the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, it can usually be arbitrarily set within the range of 5 minutes to 100 hours, and preferably within the range of 1 hour to 48 hours.

The compound represented by the formula (1-d) can be synthesized according to the methods described in Production methods 1 to 10 or the following production methods 14 to 17.

Manufacturing method 12

The compound represented by the formula (1-o) (in the formula, R ¹ , R ² , R ³ , R ⁴ , A ¹ , D and n have the same meanings as described above) is a compound containing an oxidizing agent and a production method. A compound represented by the formula (1-p) (wherein R ¹ , R ² , R ³ , R ⁴ , A ¹ and D have the same meanings as described above) by reacting according to the method described in 11. Can be prepared.

The compound represented by the formula (1-o) can be synthesized according to the methods described in Production Methods 1 to 5.

Manufacturing method 13

Formula (1-q) ^{(wherein, R 1, A 1, A} 2, A 4, A 5, D and n are as defined above, _{X 9} represents a chlorine atom, a bromine atom or an iodine atom. ), compounds described in, for example, Organic Letters [Organic Lett.] 2007, 9:3687, Tetrahedron [Tetrahedron] 1998:44, 1187, International Publication No. 2011/159839, etc. By reacting with 2-thiolhexyl 3-mercaptopropionate, sodium hydrogen sulfide, sodium sulfide or the like in accordance with the method described in (1) to (1) to (3), where R ¹ , A ¹ , A ² , A ⁴ , A ⁵ , D and n have the same meanings as described above.) can be produced.

Then, the compound represented by the formula (1-r) can be prepared, for example, according to the methods described in International Publication No. 2013/043962, International Publication No. 2013/040863, International Publication No. 2012/082566, etc. By reacting with a trifluoromethylating agent such as a reagent (5-(Trifluoromethyl) dibenzothiophenium trifluoromethanesulfonate) or a Togni reagent (1-Trifluoromethyl-3,3-dimethyl-1,2-benziodoxole), the formula (1-s) ( In the formula, R ¹ , A ¹ , A ² , A ⁴ , A ⁵ , D and n have the same meanings as described above.) can be produced.

Then, the compound represented by the formula (1-s) is reacted with an oxidizing agent according to the method described in the production method 11 to give a compound represented by the formula (1-t) (in the formula, R ¹ , A ¹ , ^{a 2, a 4, a 5} , D and n are as defined above, n '' is able to produce a compound represented by the representative.) an integer of 1 or 2.

The compound represented by the formula (1-q) can be synthesized according to the methods described in Production Methods 1 to 5.

Manufacturing method 14

Formula (2Q1-c) ^{(wherein, A 1a, A 4, A} 5, R 2 and ^{R 3} are as defined _{above, X 11} represents. A chlorine atom, a bromine atom or an iodine atom) represented by And a compound represented by formula (3D-e) (wherein R ¹ , D and n have the same meanings as described above) in a solvent or without a solvent, and in the presence of a copper catalyst in some cases. In some cases, it can be produced by reacting in the presence of a base and, in some cases, in the presence of a ligand. When a solvent is used, the solvent used may be inert to the reaction, and examples thereof include lower alcohols such as water, methanol and ethanol, diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane and the like. Aromatic hydrocarbons such as ethers, benzene, chlorobenzene, bromolobenzene, xylene and toluene, aliphatic hydrocarbons such as pentane, hexane and cyclohexane, halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane , Nitriles such as acetonitrile and propionitrile, amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, N,N'-dimethylimidazolidinone, and sulfoxides such as dimethylsulfoxide And nitrogen-containing aromatic compounds such as pyridine and quinoline, and mixed solvents thereof.

The reaction can be carried out in the presence of a copper catalyst. Examples of copper catalysts that can be used include copper(I) iodide. The equivalent of the copper catalyst can be used in the range of 0.005 to 20 equivalents relative to compound (2Q1-c), and is preferably in the range of 0.01 to 5 equivalents.

The reaction can be carried out in the presence of a base. Examples of the base that can be used include pyridine, 2,6-lutidine, 4-dimethylaminopyridine, triethylamine, diisopropylethylamine, tributylamine, 4-(dimethylamino)pyridine, 1,4-diazabicyclo[2.2.2]. ] Organic bases such as octane (DABCO), 1,8-diazabicyclo[5.4.0]-7-undecene (DBU) or 1,5-diazabicyclo[4.3.0]-5-nonene (DBN) Inorganic bases such as sodium hydroxide, potassium hydroxide, sodium hydride, sodium hydrogen carbonate, potassium carbonate, cesium carbonate and potassium phosphate. The equivalent of the base can be used in the range of 0.1 to 100 equivalents based on the compound represented by the formula (2Q1-c), and preferably 1 to 20 equivalents.

The reaction can be carried out in the presence of a ligand. Examples of the ligand that can be used include 1,10-phenanthroline, 1,2-diaminoethane, N,N'-dimethylethylenediamine and the like. The equivalent amount of the ligand can be used in the range of 0.005 to 20 equivalents, and preferably the range of 0.01 to 5 equivalents, relative to compound (2Q1-c).

The reaction temperature can be set at any temperature from −80° C. to the reflux temperature of the reaction mixture, and the range of 0° C. to the reflux temperature of the reaction mixture is preferable.

Although the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, it can usually be arbitrarily set within the range of 5 minutes to 100 hours, and preferably within the range of 1 hour to 48 hours.

As the equivalent of the substrate, the compound (3D-e) can be used in the range of 0.5 to 50 equivalents, preferably the range of 1 to 20 equivalents, relative to the compound (2Q1-c).

Then, the compound represented by the formula (4-c) is dehydrated and condensed according to the method described in the step [B] of the production method 1 to give the formula (1-u) (in the formula, A ^1a , A ⁴ , A ⁵ , R ¹ , R ² , R ³ , D and n have the same meanings as described above.) can be produced.

Some of the compounds represented by the general formula (2Q1-c) are known compounds, and some of them are commercially available. Also, other compounds can be synthesized, for example, according to the following reaction formula 4.

The compound represented by the formula (3D-e) can be synthesized, for example, according to the reaction formula 8 described below.

Manufacturing method 15

A compound represented by formula (50) (in the formula, R ² , R ³ , A ^1a , A ⁴ and A ⁵ have the same meanings as described above, and X ₁₂ represents a chlorine atom, a bromine atom or an iodine atom). And a compound represented by the formula (5-a) (wherein G ₁ , G ₂ , G ₃ and G ₄ have the same meanings as described above), according to the method described in Production method 6. By doing so, it is represented by formula (51) (in the formula, R ² , R ³ , A ^1a , A ⁴ , A ⁵ , G ₁ , G ₂ , G _3, and G ₄ have the same meanings as described above). Compounds can be produced.

Then, by reacting the compound represented by the formula (51) with the compound represented by the formula (9) according to the method described in the step [C] of the production method 3, the compound represented by the formula (1-v) (Wherein R ¹ , R ² , R ³ , A ^1a , A ⁴ , A ⁵ , G ₁ , G ₂ , G ₃ and G ₄ have the same meanings as described above). be able to.

Further, by reacting the compound represented by the formula (51) with a halogenating agent according to the method described in the step [D] of the production method 3, the compound represented by the formula (52) (in the formula, R ² and R ^{2 3} , A ^1a , A ⁴ , A ⁵ , G ₁ , G ₂ , G ₃ , G ₄ and X ₁₀ have the same meanings as described above.) can be produced.

Then, the compound represented by the formula (52) and the compound represented by the formula (24) are reacted according to the method described in the step [E] of the production method 3 to give the compound of the formula (1-v). A compound represented by can be produced.

In addition, the compound represented by the formula (1-v) is the same as the compound represented by the formula (52) and the compound represented by the formula (9) according to the method described in the step [E] of the production method 3. It can be manufactured by reacting with.

The compound represented by the formula (50) can be synthesized, for example, according to the reaction formula 9 described below.

Some of the compounds represented by formula (5-a) are known compounds, and some of them are commercially available.

Manufacturing method 16

By reacting the compound represented by the formula (50) with the compound represented by the formula (9) in a solvent or without a solvent, optionally in the presence of a base, a compound represented by the formula (53) (in the formula, R ¹ , R ² , R ³ , A ^1a , A ⁴ and A ⁵ have the same meanings as described above.) can be produced. When a solvent is used, the solvent used may be inert to the reaction, and examples thereof include lower alcohols such as water, methanol and ethanol, diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane and the like. Aromatic hydrocarbons such as ethers, benzene, chlorobenzene, bromolobenzene, xylene and toluene, aliphatic hydrocarbons such as pentane, hexane and cyclohexane, halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane , Nitriles such as acetonitrile and propionitrile, amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, N,N'-dimethylimidazolidinone, and sulfoxides such as dimethylsulfoxide And nitrogen-containing aromatic compounds such as pyridine and quinoline, and mixed solvents thereof.

The reaction can be carried out in the presence of a base. Examples of the base that can be used include pyridine, 2,6-lutidine, 4-dimethylaminopyridine, triethylamine, diisopropylethylamine, tributylamine, 4-(dimethylamino)pyridine, 1,4-diazabicyclo[2.2.2]. ] Organic bases such as octane (DABCO), 1,8-diazabicyclo[5.4.0]-7-undecene (DBU) or 1,5-diazabicyclo[4.3.0]-5-nonene (DBN) Inorganic bases such as sodium hydroxide, potassium hydroxide, sodium hydride, sodium hydrogen carbonate, potassium carbonate and cesium carbonate. The equivalent of the base can be used in the range of 0.1 to 100 equivalent based on the compound represented by the formula (50), and preferably 1 to 20 equivalent.

The reaction temperature can be set at any temperature from −80° C. to the reflux temperature of the reaction mixture, and the range of 0° C. to the reflux temperature of the reaction mixture is preferable.

Although the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, it can usually be arbitrarily set within the range of 5 minutes to 100 hours, and preferably within the range of 1 hour to 48 hours.

As the equivalent of the substrate, the compound (9) can be used in the range of 0.5 to 50 equivalents relative to the compound (50), and preferably in the range of 1 to 20 equivalents.

Then, reacting the compound represented by the formula (53) with a halogenating agent in a solvent or without a solvent, optionally in the presence of a silylating agent, optionally in the presence of a base, optionally in the presence of an acid. Accordingly, formula (54) (in the formula, R ¹ , R ² , R ³ , A ^1a , A ⁴ and A ⁵ have the same meanings as described above, and X ₁₃ represents a chlorine atom, a bromine atom or an iodine atom.). A compound represented by can be produced. When a solvent is used, the solvent used may be inert to the reaction, for example, water, fatty acids such as acetic acid, lower alcohols such as methanol and ethanol, diethyl ether, tetrahydrofuran, 1,4-dioxane, 1, Ethers such as 2-dimethoxyethane, aromatic hydrocarbons such as benzene, chlorobenzene, bromolobenzene, xylene and toluene, aliphatic hydrocarbons such as pentane, hexane and cyclohexane, dichloromethane, chloroform, 1,2-dichloroethane Halogenated hydrocarbons such as nitriles, nitriles such as acetonitrile and propionitrile, amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone and N,N'-dimethylimidazolidinone , Sulfoxides such as dimethyl sulfoxide, nitrogen-containing aromatic compounds such as pyridine and quinoline, and mixed solvents thereof.

As the halogenating agent, chlorine, bromine, iodine, N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, 1,3-dichloro-5,5-dimethylhydantoin, 1,3-dibromo-5,5- Examples thereof include dimethylhydantoin, 1,3-diiodo-5,5-dimethylhydantoin, trimethylphenylammonium tribromide and the like. The equivalent of the halogenating agent can be used in the range of 0.5 to 50 equivalents based on the compound represented by the formula (53), and is preferably in the range of 1 to 20 equivalents.

The reaction can be carried out in the presence of a silylating agent. Examples of the silylating agent that can be used include trimethylsilyl trifluoromethanesulfonate and the like. The equivalent of the silylating agent can be used in the range of 0.005 to 20 equivalents, and preferably the range of 0.01 to 5 equivalents, relative to the compound represented by the formula (53).

The reaction can be carried out in the presence of a base. Examples of the base that can be used include pyridine, 2,6-lutidine, 4-dimethylaminopyridine, triethylamine, diisopropylethylamine, tributylamine, 4-(dimethylamino)pyridine, 1,4-diazabicyclo[2.2.2]. ] Organic bases such as octane (DABCO), 1,8-diazabicyclo[5.4.0]-7-undecene (DBU) or 1,5-diazabicyclo[4.3.0]-5-nonene (DBN) Inorganic bases such as sodium hydroxide, potassium hydroxide, sodium hydride, sodium hydrogen carbonate, potassium carbonate, cesium carbonate and potassium phosphate. The equivalent amount of the base can be used in the range of 0.1 to 100 equivalents, preferably the range of 1 to 20 equivalents, relative to the compound represented by the formula (53).

The reaction can be carried out in the presence of acid. Examples of the acid that can be used include hydrobromic acid and a solution of hydrogen bromide in acetic acid. The acid equivalent can be used in the range of 0.1 to 100 equivalent based on the compound represented by the formula (53), and is preferably in the range of 1 to 20 equivalent.

The reaction temperature can be set at any temperature from −80° C. to the reflux temperature of the reaction mixture, and the range of 0° C. to the reflux temperature of the reaction mixture is preferable.

Although the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, it can usually be arbitrarily set within the range of 5 minutes to 100 hours, and preferably within the range of 1 hour to 48 hours.

Then, by reacting the compound represented by the formula (54) with the compound represented by the formula (5-a) according to the method described in the production method 6, it is represented by the formula (1-v). Compounds can be produced.

Manufacturing method 17

A compound represented by the formula (54) and a compound represented by the formula (5-b) (wherein G ₅ and Y 6 have the same meanings as described above) are prepared according to the method described in the production method 6. Are represented by the formula (1-w) (wherein R ¹ , R ² , R ³ , A ^1a , A ⁴ , A ⁵ , G ₅ and Y 6 have the same meanings as described above). Compounds can be produced.

In the reactions of Production Method 1 to Production Method 17, the reaction mixture after completion of the reaction is directly concentrated, dissolved in an organic solvent, washed with water, concentrated, poured into ice water, and subjected to usual post-treatments such as extraction with an organic solvent and concentration. The intended compound of the present invention can be obtained. Further, if necessary, it can be separated and purified by any purification method such as recrystallization, column chromatography, thin layer chromatography, liquid chromatography fractionation and the like. Further, the process may proceed to the next step without isolation and purification. In some cases, in the manufacturing method 1 step [A], the manufacturing method 3 step [A], the manufacturing method 4 step [A], the manufacturing method 5 step [A], and the manufacturing method 14 step [A], Each step [B] can be omitted by proceeding with the dehydration condensation reaction in the next step.

Among the compounds represented by formula (3D-a) and formula (3D-b) used in production method 1 and production method 5, formula (3D-a1) and formula (3D-b1) in which n represents an integer of 0. ), and the compounds represented by the formula (3D-c) used in the production method 6 and the production method 10, wherein n is an integer of 1 or 2 (3D-c1) and n are The compound represented by the formula (3D-c2), which represents an integer of 0, can be produced, for example, according to the production method described in the following reaction scheme 1.

Reaction formula 1

The compound represented by formula (5-a) is a compound represented by formula (6) (wherein Ra represents a C ₁ -C ₆ alkyl group) according to the method described in Production method 6. And represented by the formula (7-a) (wherein G ₁ , G ₂ , G ₃ and G ₄ have the same meanings as described above, and Ra represents a C ₁ -C ₆ alkyl group). Can be prepared.

Then, the compound represented by the formula (7-a) is reacted with a halogenating agent according to the method described in the production method 7 to give a compound represented by the formula (8-a) (in the formula, G ₁ and G ₂ , G ₃ and G ₄ have the same meanings as described above, Ra represents a C ₁ -C ₆ alkyl group, and X ₅ represents a chlorine atom, a bromine atom or an iodine atom.). You can

Then, the compound represented by the formula (8-a) has the formula (9) (in the formula, R ¹ has the same meaning as described above) according to the method described in the step [E] of the production method 3. The compound represented by formula (10-a) (wherein G ₁ , G ₂ , G ₃ , G ₄ and R ¹ have the same meanings as described above, and Ra is C ₁ -C _6). A compound represented by an alkyl group can be produced.

Then, the compound represented by the formula (10-a) is subjected to a hydrolysis reaction according to a known method known in the literature to give a compound of the formula (3D-a1) (in the formula, G ₁ , G ₂ , and G). ₃ , G ₄ and R ¹ have the same meanings as described above.) can be produced.

Then, by reacting the compound represented by the formula (3D-a1) with a chlorinating agent according to a known method known in the literature, the compound represented by the formula (3D-b1) (in the formula, G ₁ , G ₂ , G ₃ , G ₄ and R ¹ have the same meanings as described above.) can be produced.

Then, the compound represented by the formula (3D-b1) is reacted with the N,O-dimethylhydroxylamine represented by the formula (11) or its hydrochloride in the presence of a base, depending on the case. ) (In the formula, G ₁ , G ₂ , G ₃ , G ₄ and R ¹ have the same meanings as described above.).

Then, a compound represented by the formula (12) and a compound represented by the formula (13) (in the formula, R ⁶ has the same meaning as described above, and X ₇ represents a chlorine atom, a bromine atom or an iodine atom). By reacting a Grignard reagent according to a known method known in the literature, Formula (14) (in the formula, G ¹ , G ² , G ³ , G ⁴ , R ¹ and R ⁶ have the same meanings as described above. A compound represented by the formula) can be produced.

Then, by reacting the compound represented by the formula (14) with an oxidizing agent according to the method described in Production method 11, the compound represented by the formula (15) (in the formula, G ₁ , G ₂ , G ₃ , G ₄ , R ¹ , R ⁶ and n′ have the same meanings as described above.) can be produced.

Then, the compound represented by the formula (15) is reacted with a halogenating agent according to the method described in the step [B] of the production method 16 to give the compound of the formula (3D-c1) (wherein G ₁ , G ₂ , G ₃ , G ₄ , R ¹ , R ⁶ , X ₂ and n′ have the same meanings as described above.) can be produced.

Further, by reacting the compound represented by the formula (14) with a halogenating agent according to the method described in the step [B] of the production method 16, the compound represented by the formula (3D-c2) (in the formula, G ₁ , G ₂ , G ₃ , G ₄ , R ¹ , R ⁶ and X ₂ have the same meanings as described above.) can be produced.

Some of the compounds represented by formula (5-a) are known compounds, and some of them are commercially available.

Some of the compounds represented by formula (6) are known compounds, and some of them are commercially available.

The compound represented by the formula (11) is a known compound and can be obtained as a commercial product.

Some of the compounds represented by formula (13) are known compounds, and some of them are commercially available.

Among the compounds represented by the formula (3D-a) used in the production method 1, the compound represented by the formula (3D-a2) in which n represents an integer of 0 is, for example, the production described in Reaction Formula 2 below. It can be manufactured according to the method.

Reaction formula 2

The compound represented by the formula (5-b) is reacted with the compound represented by the formula (6) according to the method described in the production method 6, to give a compound represented by the formula (7-b) (in the formula, G ₅ , Y6 and Ra have the same meanings as described above.) can be produced.

Then, the compound represented by the formula (7-b) is reacted with a halogenating agent according to the method described in Production method 7 to give a compound represented by the formula (8-b) (in the formula, G ₅ , Y 6 and Ra represents the same meaning as described above, and X ₆ represents a chlorine atom, a bromine atom or an iodine atom.) can be produced.

Then, the compound represented by the formula (8-b) is reacted with the compound represented by the formula (9) according to the method described in the step [E] of the production method 3 to give the compound represented by the formula (10- b) (in the formula, G ₅ , Y 6, R ¹ and Ra have the same meanings as described above), and thus a compound represented by the formula (b) can be produced.

Then, the compound represented by formula (10-b) is subjected to a hydrolysis reaction according to a known method known in the literature to give formula (3D-a2) (in the formula, G ₅ , Y 6, and R ^{1 ).} Represents the same meaning as described above).

Some of the compounds represented by formula (5-b) are known compounds, and some of them are commercially available.

The compound represented by Formula (10-a) used in Reaction Scheme 1 can be produced, for example, according to the production method described in Reaction Scheme 3 below.

Reaction formula 3

The compound represented by the formula (7-a) is reacted with the compound represented by the formula (9) and a halogenating agent according to the method described in the step [C] of the production method 3 to give the compound represented by the formula (7 The compound represented by 10-a) can be produced.

Among the compounds represented by the formula (2Q1-a) used in the production method 1, the compound represented by the formula (2Q1-a-1) is produced, for example, according to the production method described in the following reaction scheme 4. You can

Reaction formula 4

A compound represented by the formula (25) (wherein R ² , R ³ and A ⁵ have the same meanings as described above) can be prepared by converting N into a compound represented by the method described in, for example, International Publication No. 2007/0939001. A compound represented by the formula (26) (in the formula, R ² , R ³ and A ⁵ have the same meanings as described above) can be produced by reacting with a brominating agent such as -bromosuccinimide. ..

Then, by reacting the compound represented by the formula (26) with the compound represented by the formula (16) according to the method described in the production method 2, the compound represented by the formula (27) (in the formula, R ² , R ³ , A ^1aa and A ⁵ have the same meanings as described above.) can be produced.

Then, the compound represented by the formula (27) is reacted with an aminating agent such as ammonia, aqueous ammonia or lithium amide according to the method described in, for example, International Publication No. 2012/086848 to give the compound represented by the formula ( 2Q1-a-1) (in the formula, R ² , R ³ , A ^1aa and A ⁵ have the same meanings as described above).

Some of the compounds represented by formula (25) are known compounds, and some of them are commercially available.

Among the compounds represented by the formula (2Q2-a) used in the production method 6, the compound represented by the formula (2Q2-a-1) is produced according to the production method described in the following reaction scheme 5, for example. You can

Reaction formula 5

A compound represented by the formula (28) (in the formula, R ² and R ³ have the same meanings as described above, and Rb represents a C ₁ -C ₆ alkyl group), for example, Journal of Fluorine Chemistry [ J. Fluorine. Chem.] 1989, 44, 361, Journal of Heterocyclic Chem. [J. Heterocyclic Chem.] 1993, 30, 49, Synthesis 2000, 1078 In the formula (29) [in the formula, Rc represents a C ₁ -C ₆ alkyl group, X ₈ represents a halogen atom, a C ₁ -C ₄ alkylsulfonate group (for example, a methanesulfonyloxy group, and the like. Etc.), a C ₁ -C ₄ haloalkyl sulfonate group (eg, trifluoromethanesulfonyloxy group, etc.) or an aryl sulfonate group (eg, benzenesulfonyloxy group, p-toluenesulfonyloxy group, etc.) and the like. .. ] The compound represented by Formula (30) (In formula, R< ² >, R< ³ >, Rb and Rc represents the same meaning as the above.) can be manufactured by making it react with the compound represented by this.

Then, the compound represented by the formula (30) is prepared according to the method described in, for example, Bioorganic & Med. Chem. Lett. By reacting with a compound represented by the formula (31) (in the formula, R ⁵ has the same meaning as described above) to obtain a compound represented by the formula (32) (in the formula, R ² , R ³ and R ⁵ are as described above). A compound represented by the same meaning can be produced.

Then, the compound represented by the formula (32) is treated with, for example, phosphorus oxychloride, thionyl chloride or oxalyl dichloride according to the method described in WO2012/061337, WO2005/033084 and the like. By reacting with a chlorinating agent, a compound represented by the formula (33) (wherein R ² , R ³ and R ⁵ have the same meanings as described above) can be produced.

Then, by reacting the compound represented by the formula (33) with aqueous ammonia according to the method described in, for example, International Publication No. WO 2012/061337 and International Publication No. 2005/033084, the compound represented by the formula (2Q2- The compound represented by a-1) can be produced.

Some of the compounds represented by formula (28) are known compounds, and some of them are commercially available.

Some of the compounds represented by formula (29) are known compounds, and some of them are commercially available.

Some of the compounds represented by formula (31) are known compounds, and some of them are commercially available.

The compound represented by Formula (3D-d) used in Production Method 8 can be produced, for example, according to the production method described in Reaction Formula 6 below.

Reaction formula 6

The compound represented by the formula (3D-a) is prepared by diphenylphosphoryl azide (DPPA) and formula (34) (in accordance with the method described in, for example, International Publication No. 2012/174312 and International Publication No. 2003/018021). In the formula, Rd represents a C ₁ -C ₆ alkyl group.) to react with a compound represented by the formula (3D-d-1) (in the formula, R ¹ , Rd, D and n are as described above). A compound represented by the same meaning can be produced.

Then, by reacting the compound represented by the formula (3D-d-1) with an acid according to the method described in, for example, WO 2012/174312 and WO 2003/018021, The compound represented by (3D-d) can be produced.

Among the compounds represented by the formula (2Q3-b) used in the production method 9, the compound represented by the formula (2Q3-b-1) is produced according to the production method described in the following reaction scheme 7, for example. You can

Reaction formula 7

The compound represented by the formula (35) (wherein R ² , R ³ and R ⁵ have the same meanings as described above) can be prepared according to, for example, WO 2013/064460 or WO 2013/064461. A compound represented by the formula (36) (wherein R ² , R ³ , R ⁵ and X ₃ have the same meanings as described above) by halogenating with a halogenating agent according to the described method. Can be manufactured.

Then, the compound represented by the formula (36) is reduced according to the method described in, for example, International Publication No. 2013/064460, International Publication No. 2013/064461, or the like, to thereby obtain the compound represented by the formula (37) (wherein R ² , R ³ , R ⁵ and X ₃ have the same meanings as described above) can be produced.

Then, by oxidizing the compound represented by the formula (37) according to the method described in, for example, International Publication No. 2013/064460, International Publication No. 2013/064461, the formula (2Q3-b-1) (Wherein R ² , R ³ , R ⁵ and X ₃ have the same meanings as described above) can be produced.

Some of the compounds represented by the formula (35) are known compounds, and some of them are commercially available. In addition, other compounds can also be synthesized from known compounds according to known methods described in the literature, for example, according to the reaction conditions described in International Publication No. 2000/039094 and the like.

Among the compounds represented by the formula (3D-e) used in the production method 14, the compound represented by the formula (3D-e1) in which n represents an integer of 0 is, for example, the production described in the following reaction formula 8. It can be manufactured according to the method.

Reaction formula 8

By reacting the compound represented by the formula (3D-b1) with aqueous ammonia according to the method described in, for example, Japanese Patent Application Publication No. 2009/108046, formula (3D-e1) (in the formula) , R ¹ , G ₁ , G ₂ , G ₃ and G ₄ have the same meanings as described above.) can be produced.

The compound represented by the formula (50) used in the production methods 15 and 16 can be produced, for example, according to the production method described in the following reaction scheme 9.

Reaction formula 9

The compound represented by the formula (2Q1-d) is reacted with the compound represented by the formula (55) according to the method described in the step [A] of the production method 1 to give the compound represented by the formula (56) (the formula Among them, R ² , R ³ , A ^1a , A ⁴ and A ⁵ have the same meanings as described above.) can be produced.

Then, by deacetylating the compound represented by the formula (56) according to the method described in, for example, Synthesis [Synthesis] 1991, page 465, the compound represented by the formula (57) (in the formula, R ² , R ³ , A ^1a , A ⁴ and A ⁵ have the same meanings as described above.] can be produced.

Then, the compound represented by the formula (57) is dehydrated and condensed according to the method described in the step [B] of the production method 1 to give the compound of the formula (58) (in the formula, R ² , R ³ and A). ^1a , A ⁴ and A ⁵ have the same meanings as described above.) can be produced.

Then, the compound represented by the formula (58) and the oxidizing agent are prepared according to the method described in, for example, Journal of Medicinal Chemistry [J. Med. Chem.] 1998, 31:545. By reacting, a compound represented by the formula (59) (in the formula, R ² , R ³ , A ^1a , A ⁴ and A ⁵ have the same meanings as described above) can be produced.

Then, the compound represented by the formula (59) and the halogenating agent are treated by the method described in the step [B] of the production method 16 or, for example, Journal of Medicinal Chemistry [J. Med. Chem.] 1988. , 31 pages, 656, Journal of Medicinal Chemistry [J. Med. Chem.] 2005, 48 pages, 7658, etc. Compounds can be produced.

The compound represented by the formula (55) is a known compound and can be obtained as a commercial product. Further, the compound represented by the formula (55) has an optically active substance due to the presence of one asymmetric carbon, but includes all optically active substances and racemates.

Formula (14-a) in which R ⁶ represents a hydrogen atom among the compounds represented by Formula (14) used in Reaction Formula 1 (wherein R ¹ , G ₁ , G ₂ , G _3, and G ₄ are A compound represented by the same meaning as described above and Me represents a methyl group can be produced, for example, according to the production method described in the following reaction scheme 10.

Reaction formula 10

The compound represented by the formula (3D-b1) is represented by the formula (60) (in the formula, Rf represents a C ₁ -C ₆ alkyl group) according to, for example, the method described in WO 2013/132376. A compound represented by formula (61) (in the formula, R ¹ , G ₁ , G ₂ , G ₃ and G ₄ have the same meanings as described above, and Rf represents C ₁ -C ₆ alkyl). A compound represented by the formula) can be produced.

Then, the compound represented by the formula (61) is hydrolyzed and decarboxylated according to the method described in, for example, International Publication No. 2013/132376, whereby the compound represented by the formula (14-a) is represented. The compound can be prepared. Some of the compounds represented by the formula (60) are known compounds, and some of them are commercially available.

Among the compounds represented by the formula (15) used in the reaction formula 1, formula (15-a) in which R ⁶ represents a hydrogen atom (in the formula, R ¹ , G ₁ , G ₂ , G ₃ , G ₄ and The compound represented by n′ has the same meaning as described above and Me represents a methyl group.) can be produced, for example, according to the production method described in the following reaction scheme 11.

Reaction formula 11

By reacting the compound represented by the formula (10-a) with an oxidizing agent according to the method described in the production method 11, the compound represented by the formula (10-c) (in the formula, G ₁ , G ₂ , and G) is reacted. ₃ , G ₄ , R ¹ , Ra and n′ have the same meanings as described above.) can be produced.
Then, by subjecting the compound represented by the formula (10-c) to a hydrolysis reaction according to a known method known in the literature, a compound represented by the formula (3D-f) (in the formula, G ₁ , G ₂ , and G) can be obtained. ₃ , G ₄ , R ¹ and n′ have the same meanings as described above.) can be produced.

Then, by reacting the compound represented by the formula (3D-f) with a chlorinating agent according to a known method known in the literature, the compound represented by the formula (3D-g) (in the formula, G ₁ , G ₂ , G ₃ , G ₄ , R ¹ and n′ have the same meanings as described above.) can be produced.

Then, by reacting the compound represented by the formula (3D-g) with the compound represented by the formula (60), for example, according to the method described in WO 2013/132376 and the like, the compound represented by the formula (62) ) (Wherein R ¹ , G ₁ , G ₂ , G ₃ and G ₄ have the same meanings as described above, and Rf represents a C ₁ -C ₆ alkyl group). it can.

Then, the compound represented by the formula (62) is hydrolyzed and decarboxylated according to the method described in, for example, International Publication No. 2013/132376, whereby the compound represented by the formula (15-a) is represented. The compound can be prepared.

The compound represented by Formula (15) used in Reaction Scheme 1 can be produced, for example, according to the production method described in Reaction Scheme 12 below.

Reaction formula 12

By reacting the compound represented by the formula (3D-g) with N,O-dimethylhydroxylamine represented by the formula (11) or a hydrochloride thereof in the presence of a base in some cases, the compound represented by the formula (12-a) ) (In the formula, G ₁ , G ₂ , G ₃ , G ₄ , R ¹ and n′ have the same meanings as described above.).

Then, the compound represented by the formula (12-a) and the Grignard reactant represented by the formula (13) are reacted according to a known method known in the literature to represent the formula (15). The compound can be prepared.

In each of these reactions, a usual post-treatment is carried out after the completion of the reaction to obtain the respective production intermediates which are the raw material compounds of the production methods 1 to 17.

Further, the respective production intermediates produced by these methods can be directly used for the reaction of the next step without isolation and purification. In some cases, in the step [B] of the reaction formula 9, the dehydration condensation reaction of the next step proceeds, so that the step [C] can be omitted.

Examples of the fused heterocyclic compound represented by the formula (1) included in the present invention which can be produced using the above method include the compounds shown in Tables 1 and 2 below. However, the compounds shown in the following Tables 1 and 2 are for exemplification, and the compounds included in the present invention are not limited to these.

In the table, the substituent described as Me represents a methyl group, and hereinafter Et represents an ethyl group, ⁿ Pr represents a normal propyl group, and ⁱ Pr represents an isopropyl group.

[Table 1]

Continuation of [Table 1] Continuation of [Table 1]
――――――――――――――――――― ―――――――――――――――――――
W1 R ¹ Y1 Y2 Y3 Y4 n W1 R ¹ Y1 Y2 Y3 Y4 n
――――――――――――――――――― ―――――――――――――――――――
CF ₃ Et HHHH 0 CF ₃ Et HIHH 1
CF ₃ Et HHHH 1 CF ₃ Et HIHH 2
CF ₃ Et HHHH 2 CF ₃ Et H Me HH 0
CF ₃ Et FHHH 0 CF ₃ Et H Me HH 1
CF ₃ Et FHHH 1 CF ₃ Et H Me HH 2
CF ₃ Et FHHH 2 CF ₃ Et H CF ₃ HH 0
CF ₃ Et Cl HHH 0 CF ₃ Et H CF ₃ HH 1
CF ₃ Et Cl HHH 1 CF ₃ Et H CF ₃ HH 2
CF ₃ Et Cl HHH 2 CF ₃ Et H CF ₂ CF ₃ HH 0
CF ₃ Et Br HHH 0 CF ₃ Et H CF ₂ CF ₃ HH 1
CF ₃ Et Br HHH 1 CF ₃ Et H CF ₂ CF ₃ HH 2
CF ₃ Et Br HHH 2 CF ₃ Et H CF(CF ₃ ) ₂ HH 0
CF ₃ Et IHHH 0 CF ₃ Et H CF(CF ₃ ) ₂ HH 1
CF ₃ Et IHHH 1 CF ₃ Et H CF(CF ₃ ) ₂ HH 2
CF ₃ Et IHHH 2 CF ₃ Et H SMe HH 0
CF ₃ Et Me HHH 0 CF ₃ Et H SMe HH 1
CF ₃ Et Me HHH 1 CF ₃ Et H SMe HH 2
CF ₃ Et Me HHH 2 CF ₃ Et H SOMe HH 0
CF ₃ Et CF ₃ HHH 0 CF ₃ Et H SOMe HH 1
CF ₃ Et CF ₃ HHH 1 CF ₃ Et H SOMe HH 2
CF ₃ Et CF ₃ HHH 2 CF ₃ Et H SO ₂ Me HH 0
CF ₃ Et HFHH 0 CF ₃ Et H SO ₂ Me HH 1
CF ₃ Et HFHH 1 CF ₃ Et H SO ₂ Me HH 2
CF ₃ Et HFHH 2 CF ₃ Et H OMe HH 0
CF ₃ Et H Cl HH 0 CF ₃ Et H OMe HH 1
CF ₃ Et H Cl HH 1 CF ₃ Et H OMe HH 2
CF ₃ Et H Cl HH 2 CF ₃ Et H OCF ₃ HH 0
CF ₃ Et H Br HH 0 CF ₃ Et H OCF ₃ HH 1
CF ₃ Et H Br HH 1 CF ₃ Et H OCF ₃ HH 2
CF ₃ Et H Br HH 2 CF ₃ Et H NO ₂ HH 0
CF ₃ Et HIHH 0 ―――――――――――――――――――
―――――――――――――――――――
Continuation of [Table 1] Continuation of [Table 1]
――――――――――――――――――― ――――――――――――――――――――
W1 R ¹ Y1 Y2 Y3 Y4 n W1 R ¹ Y1 Y2 Y3 Y4 n
――――――――――――――――――― ――――――――――――――――――――
CF ₃ Et H NO ₂ HH 1 CF ₃ Et HHHI 2
CF ₃ Et H NO ₂ HH 2 CF ₃ Et HHH Me 0
CF ₃ Et H CN HH 0 CF ₃ Et HHH Me 1
CF ₃ Et H CN HH 1 CF ₃ Et HHH Me 2
CF ₃ Et H CN HH 2 CF ₃ Et HHH CF ₃ 0
CF ₃ Et HHFH 0 CF ₃ Et HHH CF ₃ 1
CF ₃ Et HHFH 1 CF ₃ Et HHH CF ₃ 2
CF ₃ Et HHFH 2 CF ₃ Et HHH CF ₂ CF ₃ 0
CF ₃ Et HH Cl H 0 CF ₃ Et HHH CF ₂ CF ₃ 1
CF ₃ Et HH Cl H 1 CF ₃ Et HHH CF ₂ CF ₃ 2
CF ₃ Et HH Cl H 2 CF ₃ Et HHH CF(CF ₃ ) ₂ 0
CF ₃ Et HH Br H 0 CF ₃ Et HHH CF(CF ₃ ) ₂ 1
CF ₃ Et HH Br H 1 CF ₃ Et HHH CF(CF ₃ ) ₂ 2
CF ₃ Et HH Br H 2 CF ₃ Et HHH SMe 0
CF ₃ Et HHIH 0 CF ₃ Et HHH SMe 1
CF ₃ Et HHIH 1 CF ₃ Et HHH SMe 2
CF ₃ Et HHIH 2 CF ₃ Et HHH SOMe 0
CF ₃ Et HH Me H 0 CF ₃ Et HHH SOMe 1
CF ₃ Et HH Me H 1 CF ₃ Et HHH SOMe 2
CF ₃ Et HH Me H 2 CF ₃ Et HHH SO ₂ Me 0
CF ₃ Et HH CF ₃ H 0 CF ₃ Et HHH SO ₂ Me 1
CF ₃ Et HH CF ₃ H 1 CF ₃ Et HHH SO ₂ Me 2
CF ₃ Et HH CF ₃ H 2 CF ₃ Et HHH OMe 0
CF ₃ Et HH CF ₂ CF ₃ H 0 CF ₃ Et HHH OMe 1
CF ₃ Et HH CF ₂ CF ₃ H 1 CF ₃ Et HHH OMe 2
CF ₃ Et HH CF ₂ CF ₃ H 2 CF ₃ Et HHH OCF ₃ 0
CF ₃ Et HH CF(CF ₃ ) ₂ H 0 CF ₃ Et HHH OCF ₃ 1
CF ₃ Et HH CF(CF ₃ ) ₂ H 1 CF ₃ Et HHH OCF ₃ 2
CF ₃ Et HH CF(CF ₃ ) ₂ H 2 CF ₃ Et HHH NO ₂ 0
CF ₃ Et HH SMe H 0 CF ₃ Et HHH NO ₂ 1
CF ₃ Et HH SMe H 1 CF ₃ Et HHH NO ₂ 2
CF ₃ Et HH SMe H 2 CF ₃ Et HHH CN 0
CF ₃ Et HH SOMe H 0 CF ₃ Et HHH CN 1
CF ₃ Et HH SOMe H 1 CF ₃ Et HHH CN 2
CF ₃ Et HH SOMe H 2 CF ₃ Et HFHF 0
CF ₃ Et HH SO ₂ Me H 0 CF ₃ Et HFHF 1
CF ₃ Et HH SO ₂ Me H 1 CF ₃ Et HFHF 2
CF ₃ Et HH SO ₂ Me H 2 CF ₃ Et H Cl H Cl 0
CF ₃ Et HH OMe H 0 CF ₃ Et H Cl H Cl 1
CF ₃ Et HH OMe H 1 CF ₃ Et H Cl H Cl 2
CF ₃ Et HH OMe H 2 CF ₃ Et H Br H Br 0
CF ₃ Et HH OCF ₃ H 0 CF ₃ Et H Br H Br 1
CF ₃ Et HH OCF ₃ H 1 CF ₃ Et H Br H Br 2
CF ₃ Et HH OCF ₃ H 2 CF ₃ Et HIHI 0
CF ₃ Et HH NO ₂ H 0 CF ₃ Et HIHI 1
CF ₃ Et HH NO ₂ H 1 CF ₃ Et HIHI 2
CF ₃ Et HH NO ₂ H 2 CF ₃ Et HFH Cl 0
CF ₃ Et HH CN H 0 CF ₃ Et HFH Cl 1
CF ₃ Et HH CN H 1 CF ₃ Et HFH Cl 2
CF ₃ Et HH CN H 2 CF ₃ Et HFH Br 0
CF ₃ Et HHHF 0 CF ₃ Et HFH Br 1
CF ₃ Et HHHF 1 CF ₃ Et HFH Br 2
CF ₃ Et HHHF 2 CF ₃ Et HFHI 0
CF ₃ Et HHH Cl 0 CF ₃ Et HFHI 1
CF ₃ Et HHH Cl 1 CF ₃ Et HFHI 2
CF ₃ Et HHH Cl 2 CF ₃ Et H Cl HF 0
CF ₃ Et HHH Br 0 CF ₃ Et H Cl HF 1
CF ₃ Et HHH Br 1 CF ₃ Et H Cl HF 2
CF ₃ Et HHH Br 2 CF ₃ Et H Cl H Br 0
CF ₃ Et HHHI 0 CF ₃ Et H Cl H Br 1
CF ₃ Et HHHI 1 CF ₃ Et H Cl H Br 2
――――――――――――――――――― ――――――――――――――――――――
Continuation of [Table 1] Continuation of [Table 1]
――――――――――――――――――― ――――――――――――――――――――
W1 R ¹ Y1 Y2 Y3 Y4 n W1 R ¹ Y1 Y2 Y3 Y4 n
――――――――――――――――――― ――――――――――――――――――――
CF ₃ Et H Cl HI 0 CF ₃ Et HF Cl H 1
CF ₃ Et H Cl HI 1 CF ₃ Et HF Cl H 2
CF ₃ Et H Cl HI 2 CF ₃ Et HF Br H 0
CF ₃ Et H Br HF 0 CF ₃ Et HF Br H 1
CF ₃ Et H Br HF 1 CF ₃ Et HF Br H 2
CF ₃ Et H Br HF 2 CF ₃ Et HFIH 0
CF ₃ Et H Br H Cl 0 CF ₃ Et HFIH 1
CF ₃ Et H Br H Cl 1 CF ₃ Et HFIH 2
CF ₃ Et H Br H Cl 2 CF ₃ Et H Cl FH 0
CF ₃ Et H Br HI 0 CF ₃ Et H Cl FH 1
CF ₃ Et H Br HI 1 CF ₃ Et H Cl FH 2
CF ₃ Et H Br HI 2 CF ₃ Et H Cl Br H 0
CF ₃ Et HIHF 0 CF ₃ Et H Cl Br H 1
CF ₃ Et HIHF 1 CF ₃ Et H Cl Br H 2
CF ₃ Et HIHF 2 CF ₃ Et H Cl IH 0
CF ₃ Et HIH Cl 0 CF ₃ Et H Cl IH 1
CF ₃ Et HIH Cl 1 CF ₃ Et H Cl IH 2
CF ₃ Et HIH Cl 2 CF ₃ Et H Br FH 0
CF ₃ Et HIH Br 0 CF ₃ Et H Br FH 1
CF ₃ Et HIH Br 1 CF ₃ Et H Br FH 2
CF ₃ Et HIH Br 2 CF ₃ Et H Br Cl H 0
CF ₃ Et HFH CN 0 CF ₃ Et H Br Cl H 1
CF ₃ Et HFH CN 1 CF ₃ Et H Br Cl H 2
CF ₃ Et HFH CN 2 CF ₃ Et H Br IH 0
CF ₃ Et H Cl H CN 0 CF ₃ Et H Br IH 1
CF ₃ Et H Cl H CN 1 CF ₃ Et H Br IH 2
CF ₃ Et H Cl H CN 2 CF ₃ Et HIFH 0
CF ₃ Et H Br H CN 0 CF ₃ Et HIFH 1
CF ₃ Et H Br H CN 1 CF ₃ Et HIFH 2
CF ₃ Et H Br H CN 2 CF ₃ Et HI Cl H 0
CF ₃ Et HIH CN 0 CF ₃ Et HI Cl H 1
CF ₃ Et HIH CN 1 CF ₃ Et HI Cl H 2
CF ₃ Et HIH CN 2 CF ₃ Et HI Br H 0
――――――――――――――――――― ――――――――――――――――――――
Continuation of [Table 1] Continuation of [Table 1]
――――――――――――――――――― ――――――――――――――――――――
W1 R ¹ Y1 Y2 Y3 Y4 n W1 R ¹ Y1 Y2 Y3 Y4 n
――――――――――――――――――― ――――――――――――――――――――
CF ₃ Et H CF ₃ HF 0 CF ₃ Et HI Br H 1
CF ₃ Et H CF ₃ HF 1 CF ₃ Et HI Br H 2
CF ₃ Et H CF ₃ HF 2 CF ₃ Et HF CN H 0
CF ₃ Et H CF ₃ H Cl 0 CF ₃ Et HF CN H 1
CF ₃ Et H CF ₃ H Cl 1 CF ₃ Et HF CN H 2
CF ₃ Et H CF ₃ H Cl 2 CF ₃ Et H Cl CN H 0
CF ₃ Et H CF ₃ H Br 0 CF ₃ Et H Cl CN H 1
CF ₃ Et H CF ₃ H Br 1 CF ₃ Et H Cl CN H 2
CF ₃ Et H CF ₃ H Br 2 CF ₃ Et H Br CN H 0
CF ₃ Et H CF ₃ HI 0 CF ₃ Et H Br CN H 1
CF ₃ Et H CF ₃ HI 1 CF ₃ Et H Br CN H 2
CF ₃ Et H CF ₃ HI 2 CF ₃ Et HI CN H 0
CF ₃ Et H CF ₃ H CN 0 CF ₃ Et HI CN H 1
CF ₃ Et H CF ₃ H CN 1 CF ₃ Et HI CN H 2
CF ₃ Et H CF ₃ H CN 2 CF ₃ Et H CF ₃ FH 0
CF ₃ Et HFFH 0 CF ₃ Et H CF ₃ FH 1
CF ₃ Et HFFH 1 CF ₃ Et H CF ₃ FH 2
CF ₃ Et HFFH 2 CF ₃ Et H CF ₃ Cl H 0
CF ₃ Et H Cl Cl H 0 CF ₃ Et H CF ₃ Cl H 1
CF ₃ Et H Cl Cl H 1 CF ₃ Et H CF ₃ Cl H 2
CF ₃ Et H Cl Cl H 2 CF ₃ Et H CF ₃ Br H 0
CF ₃ Et H Br Br H 0 CF ₃ Et H CF ₃ Br H 1
CF ₃ Et H Br Br H 1 CF ₃ Et H CF ₃ Br H 2
CF ₃ Et H Br Br H 2 CF ₃ Et H CF ₃ IH 0
CF ₃ Et HIIH 0 CF ₃ Et H CF ₃ IH 1
CF ₃ Et HIIH 1 CF ₃ Et H CF ₃ IH 2
CF ₃ Et HIIH 2 CF ₃ Et H CF ₃ CN H 0
CF ₃ Et HF Cl H 0 CF ₃ Et H CF ₃ CN H 1
――――――――――――――――――― CF ₃ Et H CF ₃ CN H 2
――――――――――――――――――――

Continuation of [Table 1] Continuation of [Table 1]
――――――――――――――――――― ――――――――――――――――――――
W1 R ¹ Y1 Y2 Y3 Y4 n W1 R ¹ Y1 Y2 Y3 Y4 n
――――――――――――――――――― ――――――――――――――――――――
CF ₂ CF ₃ Et HHHH 0 CF ₂ CF ₃ Et H NO ₂ HH 1
CF ₂ CF ₃ Et HHHH 1 CF ₂ CF ₃ Et H NO ₂ HH 2
CF ₂ CF ₃ Et HHHH 2 CF ₂ CF ₃ Et H CN HH 0
CF ₂ CF ₃ Et FHHH 0 CF ₂ CF ₃ Et H CN HH 1
CF ₂ CF ₃ Et FHHH 1 CF ₂ CF ₃ Et H CN HH 2
CF ₂ CF ₃ Et FHHH 2 CF ₂ CF ₃ Et HHFH 0
CF ₂ CF ₃ Et Cl HHH 0 CF ₂ CF ₃ Et HHFH 1
CF ₂ CF ₃ Et Cl HHH 1 CF ₂ CF ₃ Et HHFH 2
CF ₂ CF ₃ Et Cl HHH 2 CF ₂ CF ₃ Et HH Cl H 0
CF ₂ CF ₃ Et Br HHH 0 CF ₂ CF ₃ Et HH Cl H 1
CF ₂ CF ₃ Et Br HHH 1 CF ₂ CF ₃ Et HH Cl H 2
CF ₂ CF ₃ Et Br HHH 2 CF ₂ CF ₃ Et HH Br H 0
CF ₂ CF ₃ Et IHHH 0 CF ₂ CF ₃ Et HH Br H 1
CF ₂ CF ₃ Et IHHH 1 CF ₂ CF ₃ Et HH Br H 2
CF ₂ CF ₃ Et IHHH 2 CF ₂ CF ₃ Et HHIH 0
CF ₂ CF ₃ Et Me HHH 0 CF ₂ CF ₃ Et HHIH 1
CF ₂ CF ₃ Et Me HHH 1 CF ₂ CF ₃ Et HHIH 2
CF ₂ CF ₃ Et Me HHH 2 CF ₂ CF ₃ Et HH Me H 0
CF ₂ CF ₃ Et CF ₃ HHH 0 CF ₂ CF ₃ Et HH Me H 1
CF ₂ CF ₃ Et CF ₃ HHH 1 CF ₂ CF ₃ Et HH Me H 2
CF ₂ CF ₃ Et CF ₃ HHH 2 CF ₂ CF ₃ Et HH CF ₃ H 0
CF ₂ CF ₃ Et HFHH 0 CF ₂ CF ₃ Et HH CF ₃ H 1
CF ₂ CF ₃ Et HFHH 1 CF ₂ CF ₃ Et HH CF ₃ H 2
CF ₂ CF ₃ Et HFHH 2 CF ₂ CF ₃ Et HH CF ₂ CF ₃ H 0
――――――――――――――――――― ――――――――――――――――――――
Continuation of [Table 1] Continuation of [Table 1]
――――――――――――――――――― ――――――――――――――――――――
W1 R ¹ Y1 Y2 Y3 Y4 n W1 R ¹ Y1 Y2 Y3 Y4 n
――――――――――――――――――― ――――――――――――――――――――
CF ₂ CF ₃ Et H Cl HH 0 CF ₂ CF ₃ Et HH CF ₂ CF ₃ H 1
CF ₂ CF ₃ Et H Cl HH 1 CF ₂ CF ₃ Et HH CF ₂ CF ₃ H 2
CF ₂ CF ₃ Et H Cl HH 2 CF ₂ CF ₃ Et HH CF(CF ₃ ) ₂ H 0
CF ₂ CF ₃ Et H Br HH 0 CF ₂ CF ₃ Et HH CF(CF ₃ ) ₂ H 1
CF ₂ CF ₃ Et H Br HH 1 CF ₂ CF ₃ Et HH CF(CF ₃ ) ₂ H 2
CF ₂ CF ₃ Et H Br HH 2 CF ₂ CF ₃ Et HH SMe H 0
CF ₂ CF ₃ Et HIHH 0 CF ₂ CF ₃ Et HH SMe H 1
CF ₂ CF ₃ Et HIHH 1 CF ₂ CF ₃ Et HH SMe H 2
CF ₂ CF ₃ Et HIHH 2 CF ₂ CF ₃ Et HH SOMe H 0
CF ₂ CF ₃ Et H Me HH 0 CF ₂ CF ₃ Et HH SOMe H 1
CF ₂ CF ₃ Et H Me HH 1 CF ₂ CF ₃ Et HH SOMe H 2
CF ₂ CF ₃ Et H Me HH 2 CF ₂ CF ₃ Et HH SO ₂ Me H 0
CF ₂ CF ₃ Et H CF ₃ HH 0 CF ₂ CF ₃ Et HH SO ₂ Me H 1
CF ₂ CF ₃ Et H CF ₃ HH 1 CF ₂ CF ₃ Et HH SO ₂ Me H 2
CF ₂ CF ₃ Et H CF ₃ HH 2 CF ₂ CF ₃ Et HH OMe H 0
CF ₂ CF ₃ Et H CF ₂ CF ₃ HH 0 CF ₂ CF ₃ Et HH OMe H 1
CF ₂ CF ₃ Et H CF ₂ CF ₃ HH 1 CF ₂ CF ₃ Et HH OMe H 2
CF ₂ CF ₃ Et H CF ₂ CF ₃ HH 2 CF ₂ CF ₃ Et HH OCF ₃ H 0
CF ₂ CF ₃ Et H CF(CF ₃ ) ₂ HH 0 CF ₂ CF ₃ Et HH OCF ₃ H 1
CF ₂ CF ₃ Et H CF(CF ₃ ) ₂ HH 1 CF ₂ CF ₃ Et HH OCF ₃ H 2
CF ₂ CF ₃ Et H CF(CF ₃ ) ₂ HH 2 CF ₂ CF ₃ Et HH NO ₂ H 0
CF ₂ CF ₃ Et H SMe HH 0 CF ₂ CF ₃ Et HH NO ₂ H 1
CF ₂ CF ₃ Et H SMe HH 1 CF ₂ CF ₃ Et HH NO ₂ H 2
CF ₂ CF ₃ Et H SMe HH 2 CF ₂ CF ₃ Et HH CN H 0
CF ₂ CF ₃ Et H SOMe HH 0 CF ₂ CF ₃ Et HH CN H 1
CF ₂ CF ₃ Et H SOMe HH 1 CF ₂ CF ₃ Et HH CN H 2
CF ₂ CF ₃ Et H SOMe HH 2 CF ₂ CF ₃ Et HHHF 0
CF ₂ CF ₃ Et H SO ₂ Me HH 0 CF ₂ CF ₃ Et HHHF 1
CF ₂ CF ₃ Et H SO ₂ Me HH 1 CF ₂ CF ₃ Et HHHF 2
CF ₂ CF ₃ Et H SO ₂ Me HH 2 CF ₂ CF ₃ Et HHH Cl 0
CF ₂ CF ₃ Et H OMe HH 0 CF ₂ CF ₃ Et HHH Cl 1
CF ₂ CF ₃ Et H OMe HH 1 CF ₂ CF ₃ Et HHH Cl 2
CF ₂ CF ₃ Et H OMe HH 2 CF ₂ CF ₃ Et HHH Br 0
CF ₂ CF ₃ Et H OCF ₃ HH 0 CF ₂ CF ₃ Et HHH Br 1
CF ₂ CF ₃ Et H OCF ₃ HH 1 CF ₂ CF ₃ Et HHH Br 2
CF ₂ CF ₃ Et H OCF ₃ HH 2 CF ₂ CF ₃ Et HHHI 0
CF ₂ CF ₃ Et H NO ₂ HH 0 CF ₂ CF ₃ Et HHHI 1
――――――――――――――――――― ――――――――――――――――――――
Continuation of [Table 1] Continuation of [Table 1]
――――――――――――――――――― ――――――――――――――――――――
W1 R ¹ Y1 Y2 Y3 Y4 n W1 R ¹ Y1 Y2 Y3 Y4 n
――――――――――――――――――― ――――――――――――――――――――
CF ₂ CF ₃ Et HHHI 2 CF ₂ CF ₃ Et H Cl HI 0
CF ₂ CF ₃ Et HHH Me 0 CF ₂ CF ₃ Et H Cl HI 1
CF ₂ CF ₃ Et HHH Me 1 CF ₂ CF ₃ Et H Cl HI 2
CF ₂ CF ₃ Et HHH Me 2 CF ₂ CF ₃ Et H Br HF 0
CF ₂ CF ₃ Et HHH CF ₃ 0 CF ₂ CF ₃ Et H Br HF 1
CF ₂ CF ₃ Et HHH CF ₃ 1 CF ₂ CF ₃ Et H Br HF 2
CF ₂ CF ₃ Et HHH CF ₃ 2 CF ₂ CF ₃ Et H Br H Cl 0
CF ₂ CF ₃ Et HHH CF ₂ CF ₃ 0 CF ₂ CF ₃ Et H Br H Cl 1
CF ₂ CF ₃ Et HHH CF ₂ CF ₃ 1 CF ₂ CF ₃ Et H Br H Cl 2
CF ₂ CF ₃ Et HHH CF ₂ CF ₃ 2 CF ₂ CF ₃ Et H Br HI 0
CF ₂ CF ₃ Et HHH CF(CF ₃ ) ₂ 0 CF ₂ CF ₃ Et H Br HI 1
CF ₂ CF ₃ Et HHH CF(CF ₃ ) ₂ 1 CF ₂ CF ₃ Et H Br HI 2
CF ₂ CF ₃ Et HHH CF(CF ₃ ) ₂ 2 CF ₂ CF ₃ Et HIHF 0
CF ₂ CF ₃ Et HHH SMe 0 CF ₂ CF ₃ Et HIHF 1
CF ₂ CF ₃ Et HHH SMe 1 CF ₂ CF ₃ Et HIHF 2
CF ₂ CF ₃ Et HHH SMe 2 CF ₂ CF ₃ Et HIH Cl 0
CF ₂ CF ₃ Et HHH SOMe 0 CF ₂ CF ₃ Et HIH Cl 1
CF ₂ CF ₃ Et HHH SOMe 1 CF ₂ CF ₃ Et HIH Cl 2
CF ₂ CF ₃ Et HHH SOMe 2 CF ₂ CF ₃ Et HIH Br 0
CF ₂ CF ₃ Et HHH SO ₂ Me 0 CF ₂ CF ₃ Et HIH Br 1
CF ₂ CF ₃ Et HHH SO ₂ Me 1 CF ₂ CF ₃ Et HIH Br 2
CF ₂ CF ₃ Et HHH SO ₂ Me 2 CF ₂ CF ₃ Et HFH CN 0
CF ₂ CF ₃ Et HHH OMe 0 CF ₂ CF ₃ Et HFH CN 1
CF ₂ CF ₃ Et HHH OMe 1 CF ₂ CF ₃ Et HFH CN 2
CF ₂ CF ₃ Et HHH OMe 2 CF ₂ CF ₃ Et H Cl H CN 0
CF ₂ CF ₃ Et HHH OCF ₃ 0 CF ₂ CF ₃ Et H Cl H CN 1
CF ₂ CF ₃ Et HHH OCF ₃ 1 CF ₂ CF ₃ Et H Cl H CN 2
CF ₂ CF ₃ Et HHH OCF ₃ 2 CF ₂ CF ₃ Et H Br H CN 0
CF ₂ CF ₃ Et HHH NO ₂ 0 CF ₂ CF ₃ Et H Br H CN 1
CF ₂ CF ₃ Et HHH NO ₂ 1 CF ₂ CF ₃ Et H Br H CN 2
CF ₂ CF ₃ Et HHH NO ₂ 2 CF ₂ CF ₃ Et HIH CN 0
CF ₂ CF ₃ Et HHH CN 0 CF ₂ CF ₃ Et HIH CN 1
CF ₂ CF ₃ Et HHH CN 1 CF ₂ CF ₃ Et HIH CN 2
CF ₂ CF ₃ Et HHH CN 2 CF ₂ CF ₃ Et H CF ₃ HF 0
――――――――――――――――――― ――――――――――――――――――――
Continuation of [Table 1] Continuation of [Table 1]
――――――――――――――――――― ――――――――――――――――――――
W1 R ¹ Y1 Y2 Y3 Y4 n W1 R ¹ Y1 Y2 Y3 Y4 n
――――――――――――――――――― ――――――――――――――――――――
CF ₂ CF ₃ Et HFHF 0 CF ₂ CF ₃ Et H CF ₃ HF 1
CF ₂ CF ₃ Et HFHF 1 CF ₂ CF ₃ Et H CF ₃ HF 2
CF ₂ CF ₃ Et HFHF 2 CF ₂ CF ₃ Et H CF ₃ H Cl 0
CF ₂ CF ₃ Et H Cl H Cl 0 CF ₂ CF ₃ Et H CF ₃ H Cl 1
CF ₂ CF ₃ Et H Cl H Cl 1 CF ₂ CF ₃ Et H CF ₃ H Cl 2
CF ₂ CF ₃ Et H Cl H Cl 2 CF ₂ CF ₃ Et H CF ₃ H Br 0
CF ₂ CF ₃ Et H Br H Br 0 CF ₂ CF ₃ Et H CF ₃ H Br 1
CF ₂ CF ₃ Et H Br H Br 1 CF ₂ CF ₃ Et H CF ₃ H Br 2
CF ₂ CF ₃ Et H Br H Br 2 CF ₂ CF ₃ Et H CF ₃ HI 0
CF ₂ CF ₃ Et HIHI 0 CF ₂ CF ₃ Et H CF ₃ HI 1
CF ₂ CF ₃ Et HIHI 1 CF ₂ CF ₃ Et H CF ₃ HI 2
CF ₂ CF ₃ Et HIHI 2 CF ₂ CF ₃ Et H CF ₃ H CN 0
CF ₂ CF ₃ Et HFH Cl 0 CF ₂ CF ₃ Et H CF ₃ H CN 1
CF ₂ CF ₃ Et HFH Cl 1 CF ₂ CF ₃ Et H CF ₃ H CN 2
CF ₂ CF ₃ Et HFH Cl 2 CF ₂ CF ₃ Et HFFH 0
CF ₂ CF ₃ Et HFH Br 0 CF ₂ CF ₃ Et HFFH 1
CF ₂ CF ₃ Et HFH Br 1 CF ₂ CF ₃ Et HFFH 2
CF ₂ CF ₃ Et HFH Br 2 CF ₂ CF ₃ Et H Cl Cl H 0
CF ₂ CF ₃ Et HFHI 0 CF ₂ CF ₃ Et H Cl Cl H 1
CF ₂ CF ₃ Et HFHI 1 CF ₂ CF ₃ Et H Cl Cl H 2
CF ₂ CF ₃ Et HFHI 2 CF ₂ CF ₃ Et H Br Br H 0
CF ₂ CF ₃ Et H Cl HF 0 CF ₂ CF ₃ Et H Br Br H 1
CF ₂ CF ₃ Et H Cl HF 1 CF ₂ CF ₃ Et H Br Br H 2
CF ₂ CF ₃ Et H Cl HF 2 CF ₂ CF ₃ Et HIIH 0
CF ₂ CF ₃ Et H Cl H Br 0 CF ₂ CF ₃ Et HIIH 1
CF ₂ CF ₃ Et H Cl H Br 1 CF ₂ CF ₃ Et HIIH 2
CF ₂ CF ₃ Et H Cl H Br 2 CF ₂ CF ₃ Et HF Cl H 0
――――――――――――――――――― ――――――――――――――――――――
Continuation of [Table 1] Continuation of [Table 1]
――――――――――――――――――― ――――――――――――――――――――
W1 R ¹ Y1 Y2 Y3 Y4 n W1 R ¹ Y1 Y2 Y3 Y4 n
――――――――――――――――――― ――――――――――――――――――――
CF ₂ CF ₃ Et HF Cl H 1 SCF ₃ Et HHHH 0
CF ₂ CF ₃ Et HF Cl H 2 SCF ₃ Et HHHH 1
CF ₂ CF ₃ Et HF Br H 0 SCF ₃ Et HHHH 2
CF ₂ CF ₃ Et HF Br H 1 SCF ₃ Et FHHH 0
CF ₂ CF ₃ Et HF Br H 2 SCF ₃ Et FHHH 1
CF ₂ CF ₃ Et HFIH 0 SCF ₃ Et FHHH 2
CF ₂ CF ₃ Et HFIH 1 SCF ₃ Et Cl HHH 0
CF ₂ CF ₃ Et HFIH 2 SCF ₃ Et Cl HHH 1
CF ₂ CF ₃ Et H Cl FH 0 SCF ₃ Et Cl HHH 2
CF ₂ CF ₃ Et H Cl FH 1 SCF ₃ Et Br HHH 0
CF ₂ CF ₃ Et H Cl FH 2 SCF ₃ Et Br HHH 1
CF ₂ CF ₃ Et H Cl Br H 0 SCF ₃ Et Br HHH 2
CF ₂ CF ₃ Et H Cl Br H 1 SCF ₃ Et IHHH 0
CF ₂ CF ₃ Et H Cl Br H 2 SCF ₃ Et IHHH 1
CF ₂ CF ₃ Et H Cl IH 0 SCF ₃ Et IHHH 2
CF ₂ CF ₃ Et H Cl IH 1 SCF ₃ Et Me HHH 0
CF ₂ CF ₃ Et H Cl IH 2 SCF ₃ Et Me HHH 1
CF ₂ CF ₃ Et H Br FH 0 SCF ₃ Et Me HHH 2
CF ₂ CF ₃ Et H Br FH 1 SCF ₃ Et CF ₃ HHH 0
CF ₂ CF ₃ Et H Br FH 2 SCF ₃ Et CF ₃ HHH 1
CF ₂ CF ₃ Et H Br Cl H 0 SCF ₃ Et CF ₃ HHH 2
CF ₂ CF ₃ Et H Br Cl H 1 SCF ₃ Et HFHH 0
CF ₂ CF ₃ Et H Br Cl H 2 SCF ₃ Et HFHH 1
――――――――――――――――――― ――――――――――――――――――――
Continuation of [Table 1] Continuation of [Table 1]
――――――――――――――――――― ――――――――――――――――――――
W1 R ¹ Y1 Y2 Y3 Y4 n W1 R ¹ Y1 Y2 Y3 Y4 n
――――――――――――――――――― ――――――――――――――――――――
CF ₂ CF ₃ Et H Br IH 0 SCF ₃ Et HFHH 2
CF ₂ CF ₃ Et H Br IH 1 SCF ₃ Et H Cl HH 0
CF ₂ CF ₃ Et H Br IH 2 SCF ₃ Et H Cl HH 1
CF ₂ CF ₃ Et HIFH 0 SCF ₃ Et H Cl HH 2
CF ₂ CF ₃ Et HIFH 1 SCF ₃ Et H Br HH 0
CF ₂ CF ₃ Et HIFH 2 SCF ₃ Et H Br HH 1
CF ₂ CF ₃ Et HI Cl H 0 SCF ₃ Et H Br HH 2
CF ₂ CF ₃ Et HI Cl H 1 SCF ₃ Et HIHH 0
CF ₂ CF ₃ Et HI Cl H 2 SCF ₃ Et HIHH 1
CF ₂ CF ₃ Et HI Br H 0 SCF ₃ Et HIHH 2
CF ₂ CF ₃ Et HI Br H 1 SCF ₃ Et H Me HH 0
CF ₂ CF ₃ Et HI Br H 2 SCF ₃ Et H Me HH 1
CF ₂ CF ₃ Et HF CN H 0 SCF ₃ Et H Me HH 2
CF ₂ CF ₃ Et HF CN H 1 SCF ₃ Et H CF ₃ HH 0
CF ₂ CF ₃ Et HF CN H 2 SCF ₃ Et H CF ₃ HH 1
CF ₂ CF ₃ Et H Cl CN H 0 SCF ₃ Et H CF ₃ HH 2
CF ₂ CF ₃ Et H Cl CN H 1 SCF ₃ Et H CF ₂ CF ₃ HH 0
CF ₂ CF ₃ Et H Cl CN H 2 SCF ₃ Et H CF ₂ CF ₃ HH 1
CF ₂ CF ₃ Et H Br CN H 0 SCF ₃ Et H CF ₂ CF ₃ HH 2
CF ₂ CF ₃ Et H Br CN H 1 SCF ₃ Et H CF(CF ₃ ) ₂ HH 0
CF ₂ CF ₃ Et H Br CN H 2 SCF ₃ Et H CF(CF ₃ ) ₂ HH 1
CF ₂ CF ₃ Et HI CN H 0 SCF ₃ Et H CF(CF ₃ ) ₂ HH 2
CF ₂ CF ₃ Et HI CN H 1 SCF ₃ Et H SMe HH 0
CF ₂ CF ₃ Et HI CN H 2 SCF ₃ Et H SMe HH 1
CF ₂ CF ₃ Et H CF ₃ FH 0 SCF ₃ Et H SMe HH 2
CF ₂ CF ₃ Et H CF ₃ FH 1 SCF ₃ Et H SOMe HH 0
CF ₂ CF ₃ Et H CF ₃ FH 2 SCF ₃ Et H SOMe HH 1
CF ₂ CF ₃ Et H CF ₃ Cl H 0 SCF ₃ Et H SOMe HH 2
CF ₂ CF ₃ Et H CF ₃ Cl H 1 SCF ₃ Et H SO ₂ Me HH 0
CF ₂ CF ₃ Et H CF ₃ Cl H 2 SCF ₃ Et H SO ₂ Me HH 1
CF ₂ CF ₃ Et H CF ₃ Br H 0 SCF ₃ Et H SO ₂ Me HH 2
CF ₂ CF ₃ Et H CF ₃ Br H 1 SCF ₃ Et H OMe HH 0
CF ₂ CF ₃ Et H CF ₃ Br H 2 SCF ₃ Et H OMe HH 1
CF ₂ CF ₃ Et H CF ₃ IH 0 SCF ₃ Et H OMe HH 2
CF ₂ CF ₃ Et H CF ₃ IH 1 SCF ₃ Et H OCF ₃ HH 0
CF ₂ CF ₃ Et H CF ₃ IH 2 SCF ₃ Et H OCF ₃ HH 1
CF ₂ CF ₃ Et H CF ₃ CN H 0 SCF ₃ Et H OCF ₃ HH 2
CF ₂ CF ₃ Et H CF ₃ CN H 1 SCF ₃ Et H NO ₂ HH 0
CF ₂ CF ₃ Et H CF ₃ CN H 2 ――――――――――――――――――――――
―――――――――――――――――――
Continuation of [Table 1] Continuation of [Table 1]
――――――――――――――――――― ――――――――――――――――――――
W1 R ¹ Y1 Y2 Y3 Y4 n W1 R ¹ Y1 Y2 Y3 Y4 n
――――――――――――――――――― ――――――――――――――――――――
SCF ₃ Et H NO ₂ HH 1 SCF ₃ Et HHHI 2
SCF ₃ Et H NO ₂ HH 2 SCF ₃ Et HHH Me 0
SCF ₃ Et H CN HH 0 SCF ₃ Et HHH Me 1
SCF ₃ Et H CN HH 1 SCF ₃ Et HHH Me 2
SCF ₃ Et H CN HH 2 SCF ₃ Et HHH CF ₃ 0
SCF ₃ Et HHFH 0 SCF ₃ Et HHH CF ₃ 1
SCF ₃ Et HHFH 1 SCF ₃ Et HHH CF ₃ 2
SCF ₃ Et HHFH 2 SCF ₃ Et HHH CF ₂ CF ₃ 0
SCF ₃ Et HH Cl H 0 SCF ₃ Et HHH CF ₂ CF ₃ 1
SCF ₃ Et HH Cl H 1 SCF ₃ Et HHH CF ₂ CF ₃ 2
SCF ₃ Et HH Cl H 2 SCF ₃ Et HHH CF(CF ₃ ) ₂ 0
SCF ₃ Et HH Br H 0 SCF ₃ Et HHH CF(CF ₃ ) ₂ 1
SCF ₃ Et HH Br H 1 SCF ₃ Et HHH CF(CF ₃ ) ₂ 2
SCF ₃ Et HH Br H 2 SCF ₃ Et HHH SMe 0
SCF ₃ Et HHIH 0 SCF ₃ Et HHH SMe 1
SCF ₃ Et HHIH 1 SCF ₃ Et HHH SMe 2
SCF ₃ Et HHIH 2 SCF ₃ Et HHH SOMe 0
SCF ₃ Et HH Me H 0 SCF ₃ Et HHH SOMe 1
SCF ₃ Et HH Me H 1 SCF ₃ Et HHH SOMe 2
SCF ₃ Et HH Me H 2 SCF ₃ Et HHH SO ₂ Me 0
SCF ₃ Et HH CF ₃ H 0 SCF ₃ Et HHH SO ₂ Me 1
SCF ₃ Et HH CF ₃ H 1 SCF ₃ Et HHH SO ₂ Me 2
SCF ₃ Et HH CF ₃ H 2 SCF ₃ Et HHH OMe 0
SCF ₃ Et HH CF ₂ CF ₃ H 0 SCF ₃ Et HHH OMe 1
SCF ₃ Et HH CF ₂ CF ₃ H 1 SCF ₃ Et HHH OMe 2
SCF ₃ Et HH CF ₂ CF ₃ H 2 SCF ₃ Et HHH OCF ₃ 0
SCF ₃ Et HH CF(CF ₃ ) ₂ H 0 SCF ₃ Et HHH OCF ₃ 1
SCF ₃ Et HH CF(CF ₃ ) ₂ H 1 SCF ₃ Et HHH OCF ₃ 2
SCF ₃ Et HH CF(CF ₃ ) ₂ H 2 SCF ₃ Et HHH NO ₂ 0
SCF ₃ Et HH SMe H 0 SCF ₃ Et HHH NO ₂ 1
SCF ₃ Et HH SMe H 1 SCF ₃ Et HHH NO ₂ 2
SCF ₃ Et HH SMe H 2 SCF ₃ Et HHH CN 0
SCF ₃ Et HH SOMe H 0 SCF ₃ Et HHH CN 1
SCF ₃ Et HH SOMe H 1 SCF ₃ Et HHH CN 2
SCF ₃ Et HH SOMe H 2 SCF ₃ Et HFHF 0
――――――――――――――――――― ――――――――――――――――――――
Continuation of [Table 1] Continuation of [Table 1]
――――――――――――――――――― ――――――――――――――――――――
W1 R ¹ Y1 Y2 Y3 Y4 n W1 R ¹ Y1 Y2 Y3 Y4 n
――――――――――――――――――― ――――――――――――――――――――
SCF ₃ Et HH SO ₂ Me H 0 SCF ₃ Et HFHF 1
SCF ₃ Et HH SO ₂ Me H 1 SCF ₃ Et HFHF 2
SCF ₃ Et HH SO ₂ Me H 2 SCF ₃ Et H Cl H Cl 0
SCF ₃ Et HH OMe H 0 SCF ₃ Et H Cl H Cl 1
SCF ₃ Et HH OMe H 1 SCF ₃ Et H Cl H Cl 2
SCF ₃ Et HH OMe H 2 SCF ₃ Et H Br H Br 0
SCF ₃ Et HH OCF ₃ H 0 SCF ₃ Et H Br H Br 1
SCF ₃ Et HH OCF ₃ H 1 SCF ₃ Et H Br H Br 2
SCF ₃ Et HH OCF ₃ H 2 SCF ₃ Et HIHI 0
SCF ₃ Et HH NO ₂ H 0 SCF ₃ Et HIHI 1
SCF ₃ Et HH NO ₂ H 1 SCF ₃ Et HIHI 2
SCF ₃ Et HH NO ₂ H 2 SCF ₃ Et HFH Cl 0
SCF ₃ Et HH CN H 0 SCF ₃ Et HFH Cl 1
SCF ₃ Et HH CN H 1 SCF ₃ Et HFH Cl 2
SCF ₃ Et HH CN H 2 SCF ₃ Et HFH Br 0
SCF ₃ Et HHHF 0 SCF ₃ Et HFH Br 1
SCF ₃ Et HHHF 1 SCF ₃ Et HFH Br 2
SCF ₃ Et HHHF 2 SCF ₃ Et HFHI 0
SCF ₃ Et HHH Cl 0 SCF ₃ Et HFHI 1
SCF ₃ Et HHH Cl 1 SCF ₃ Et HFHI 2
SCF ₃ Et HHH Cl 2 SCF ₃ Et H Cl HF 0
SCF ₃ Et HHH Br 0 SCF ₃ Et H Cl HF 1
SCF ₃ Et HHH Br 1 SCF ₃ Et H Cl HF 2
SCF ₃ Et HHH Br 2 SCF ₃ Et H Cl H Br 0
SCF ₃ Et HHHI 0 SCF ₃ Et H Cl H Br 1
SCF ₃ Et HHHI 1 SCF ₃ Et H Cl H Br 2
――――――――――――――――――― ――――――――――――――――――――
Continuation of [Table 1] Continuation of [Table 1]
――――――――――――――――――― ――――――――――――――――――――
W1 R ¹ Y1 Y2 Y3 Y4 n W1 R ¹ Y1 Y2 Y3 Y4 n
――――――――――――――――――― ――――――――――――――――――――
SCF ₃ Et H Cl HI 0 SCF ₃ Et HF Cl H 1
SCF ₃ Et H Cl HI 1 SCF ₃ Et HF Cl H 2
SCF ₃ Et H Cl HI 2 SCF ₃ Et HF Br H 0
SCF ₃ Et H Br HF 0 SCF ₃ Et HF Br H 1
SCF ₃ Et H Br HF 1 SCF ₃ Et HF Br H 2
SCF ₃ Et H Br HF 2 SCF ₃ Et HFIH 0
SCF ₃ Et H Br H Cl 0 SCF ₃ Et HFIH 1
SCF ₃ Et H Br H Cl 1 SCF ₃ Et HFIH 2
SCF ₃ Et H Br H Cl 2 SCF ₃ Et H Cl FH 0
SCF ₃ Et H Br HI 0 SCF ₃ Et H Cl FH 1
SCF ₃ Et H Br HI 1 SCF ₃ Et H Cl FH 2
SCF ₃ Et H Br HI 2 SCF ₃ Et H Cl Br H 0
SCF ₃ Et HIHF 0 SCF ₃ Et H Cl Br H 1
SCF ₃ Et HIHF 1 SCF ₃ Et H Cl Br H 2
SCF ₃ Et HIHF 2 SCF ₃ Et H Cl IH 0
SCF ₃ Et HIH Cl 0 SCF ₃ Et H Cl IH 1
SCF ₃ Et HIH Cl 1 SCF ₃ Et H Cl IH 2
SCF ₃ Et HIH Cl 2 SCF ₃ Et H Br FH 0
SCF ₃ Et HIH Br 0 SCF ₃ Et H Br FH 1
SCF ₃ Et HIH Br 1 SCF ₃ Et H Br FH 2
SCF ₃ Et HIH Br 2 SCF ₃ Et H Br Cl H 0
SCF ₃ Et HFH CN 0 SCF ₃ Et H Br Cl H 1
SCF ₃ Et HFH CN 1 SCF ₃ Et H Br Cl H 2
SCF ₃ Et HFH CN 2 SCF ₃ Et H Br IH 0
SCF ₃ Et H Cl H CN 0 SCF ₃ Et H Br IH 1
SCF ₃ Et H Cl H CN 1 SCF ₃ Et H Br IH 2
SCF ₃ Et H Cl H CN 2 SCF ₃ Et HIFH 0
――――――――――――――――――― ――――――――――――――――――――
Continuation of [Table 1] Continuation of [Table 1]
――――――――――――――――――― ――――――――――――――――――――
W1 R ¹ Y1 Y2 Y3 Y4 n W1 R ¹ Y1 Y2 Y3 Y4 n
――――――――――――――――――― ――――――――――――――――――――
SCF ₃ Et H Br H CN 0 SCF ₃ Et HIFH 1
SCF ₃ Et H Br H CN 1 SCF ₃ Et HIFH 2
SCF ₃ Et H Br H CN 2 SCF ₃ Et HI Cl H 0
SCF ₃ Et HIH CN 0 SCF ₃ Et HI Cl H 1
SCF ₃ Et HIH CN 1 SCF ₃ Et HI Cl H 2
SCF ₃ Et HIH CN 2 SCF ₃ Et HI Br H 0
SCF ₃ Et H CF ₃ HF 0 SCF ₃ Et HI Br H 1
SCF ₃ Et H CF ₃ HF 1 SCF ₃ Et HI Br H 2
SCF ₃ Et H CF ₃ HF 2 SCF ₃ Et HF CN H 0
SCF ₃ Et H CF ₃ H Cl 0 SCF ₃ Et HF CN H 1
SCF ₃ Et H CF ₃ H Cl 1 SCF ₃ Et HF CN H 2
SCF ₃ Et H CF ₃ H Cl 2 SCF ₃ Et H Cl CN H 0
SCF ₃ Et H CF ₃ H Br 0 SCF ₃ Et H Cl CN H 1
SCF ₃ Et H CF ₃ H Br 1 SCF ₃ Et H Cl CN H 2
SCF ₃ Et H CF ₃ H Br 2 SCF ₃ Et H Br CN H 0
SCF ₃ Et H CF ₃ HI 0 SCF ₃ Et H Br CN H 1
SCF ₃ Et H CF ₃ HI 1 SCF ₃ Et H Br CN H 2
SCF ₃ Et H CF ₃ HI 2 SCF ₃ Et HI CN H 0
SCF ₃ Et H CF ₃ H CN 0 SCF ₃ Et HI CN H 1
SCF ₃ Et H CF ₃ H CN 1 SCF ₃ Et HI CN H 2
SCF ₃ Et H CF ₃ H CN 2 SCF ₃ Et H CF ₃ FH 0
SCF ₃ Et HFFH 0 SCF ₃ Et H CF ₃ FH 1
SCF ₃ Et HFFH 1 SCF ₃ Et H CF ₃ FH 2
SCF ₃ Et HFFH 2 SCF ₃ Et H CF ₃ Cl H 0
SCF ₃ Et H Cl Cl H 0 SCF ₃ Et H CF ₃ Cl H 1
SCF ₃ Et H Cl Cl H 1 SCF ₃ Et H CF ₃ Cl H 2
SCF ₃ Et H Cl Cl H 2 SCF ₃ Et H CF ₃ Br H 0
SCF ₃ Et H Br Br H 0 SCF ₃ Et H CF ₃ Br H 1
SCF ₃ Et H Br Br H 1 SCF ₃ Et H CF ₃ Br H 2
SCF ₃ Et H Br Br H 2 SCF ₃ Et H CF ₃ IH 0
SCF ₃ Et HIIH 0 SCF ₃ Et H CF ₃ IH 1
SCF ₃ Et HIIH 1 SCF ₃ Et H CF ₃ IH 2
SCF ₃ Et HIIH 2 SCF ₃ Et H CF ₃ CN H 0
SCF ₃ Et HF Cl H 0 SCF ₃ Et H CF ₃ CN H 1
――――――――――――――――――― SCF ₃ Et H CF ₃ CN H 2
――――――――――――――――――――

Continuation of [Table 1] Continuation of [Table 1]
――――――――――――――――――― ――――――――――――――――――――
W1 R ¹ Y1 Y2 Y3 Y4 n W1 R ¹ Y1 Y2 Y3 Y4 n
――――――――――――――――――― ――――――――――――――――――――
SOCF ₃ Et HHHH 0 SOCF ₃ Et H NO ₂ HH 1
SOCF ₃ Et HHHH 1 SOCF ₃ Et H NO ₂ HH 2
SOCF ₃ Et HHHH 2 SOCF ₃ Et H CN HH 0
SOCF ₃ Et FHHH 0 SOCF ₃ Et H CN HH 1
SOCF ₃ Et FHHH 1 SOCF ₃ Et H CN HH 2
SOCF ₃ Et FHHH 2 SOCF ₃ Et HHFH 0
SOCF ₃ Et Cl HHH 0 SOCF ₃ Et HHFH 1
SOCF ₃ Et Cl HHH 1 SOCF ₃ Et HHFH 2
SOCF ₃ Et Cl HHH 2 SOCF ₃ Et HH Cl H 0
SOCF ₃ Et Br HHH 0 SOCF ₃ Et HH Cl H 1
SOCF ₃ Et Br HHH 1 SOCF ₃ Et HH Cl H 2
SOCF ₃ Et Br HHH 2 SOCF ₃ Et HH Br H 0
SOCF ₃ Et IHHH 0 SOCF ₃ Et HH Br H 1
SOCF ₃ Et IHHH 1 SOCF ₃ Et HH Br H 2
SOCF ₃ Et IHHH 2 SOCF ₃ Et HHIH 0
SOCF ₃ Et Me HHH 0 SOCF ₃ Et HHIH 1
SOCF ₃ Et Me HHH 1 SOCF ₃ Et HHIH 2
SOCF ₃ Et Me HHH 2 SOCF ₃ Et HH Me H 0
SOCF ₃ Et CF ₃ HHH 0 SOCF ₃ Et HH Me H 1
SOCF ₃ Et CF ₃ HHH 1 SOCF ₃ Et HH Me H 2
SOCF ₃ Et CF ₃ HHH 2 SOCF ₃ Et HH CF ₃ H 0
SOCF ₃ Et HFHH 0 SOCF ₃ Et HH CF ₃ H 1
SOCF ₃ Et HFHH 1 SOCF ₃ Et HH CF ₃ H 2
SOCF ₃ Et HFHH 2 SOCF ₃ Et HH CF ₂ CF ₃ H 0
SOCF ₃ Et H Cl HH 0 SOCF ₃ Et HH CF ₂ CF ₃ H 1
SOCF ₃ Et H Cl HH 1 SOCF ₃ Et HH CF ₂ CF ₃ H 2
SOCF ₃ Et H Cl HH 2 SOCF ₃ Et HH CF(CF ₃ ) ₂ H 0
SOCF ₃ Et H Br HH 0 SOCF ₃ Et HH CF(CF ₃ ) ₂ H 1
SOCF ₃ Et H Br HH 1 SOCF ₃ Et HH CF(CF ₃ ) ₂ H 2
SOCF ₃ Et H Br HH 2 SOCF ₃ Et HH SMe H 0
――――――――――――――――――― ――――――――――――――――――――
Continuation of [Table 1] Continuation of [Table 1]
――――――――――――――――――― ――――――――――――――――――――
W1 R ¹ Y1 Y2 Y3 Y4 n W1 R ¹ Y1 Y2 Y3 Y4 n
――――――――――――――――――― ――――――――――――――――――――
SOCF ₃ Et HIHH 0 SOCF ₃ Et HH SMe H 1
SOCF ₃ Et HIHH 1 SOCF ₃ Et HH SMe H 2
SOCF ₃ Et HIHH 2 SOCF ₃ Et HH SOMe H 0
SOCF ₃ Et H Me HH 0 SOCF ₃ Et HH SOMe H 1
SOCF ₃ Et H Me HH 1 SOCF ₃ Et HH SOMe H 2
SOCF ₃ Et H Me HH 2 SOCF ₃ Et HH SO ₂ Me H 0
SOCF ₃ Et H CF ₃ HH 0 SOCF ₃ Et HH SO ₂ Me H 1
SOCF ₃ Et H CF ₃ HH 1 SOCF ₃ Et HH SO ₂ Me H 2
SOCF ₃ Et H CF ₃ HH 2 SOCF ₃ Et HH OMe H 0
SOCF ₃ Et H CF ₂ CF ₃ HH 0 SOCF ₃ Et HH OMe H 1
SOCF ₃ Et H CF ₂ CF ₃ HH 1 SOCF ₃ Et HH OMe H 2
SOCF ₃ Et H CF ₂ CF ₃ HH 2 SOCF ₃ Et HH OCF ₃ H 0
SOCF ₃ Et H CF(CF ₃ ) ₂ HH 0 SOCF ₃ Et HH OCF ₃ H 1
SOCF ₃ Et H CF(CF ₃ ) ₂ HH 1 SOCF ₃ Et HH OCF ₃ H 2
SOCF ₃ Et H CF(CF ₃ ) ₂ HH 2 SOCF ₃ Et HH NO ₂ H 0
SOCF ₃ Et H SMe HH 0 SOCF ₃ Et HH NO ₂ H 1
SOCF ₃ Et H SMe HH 1 SOCF ₃ Et HH NO ₂ H 2
SOCF ₃ Et H SMe HH 2 SOCF ₃ Et HH CN H 0
SOCF ₃ Et H SOMe HH 0 SOCF ₃ Et HH CN H 1
SOCF ₃ Et H SOMe HH 1 SOCF ₃ Et HH CN H 2
SOCF ₃ Et H SOMe HH 2 SOCF ₃ Et HHHF 0
SOCF ₃ Et H SO ₂ Me HH 0 SOCF ₃ Et HHHF 1
SOCF ₃ Et H SO ₂ Me HH 1 SOCF ₃ Et HHHF 2
SOCF ₃ Et H SO ₂ Me HH 2 SOCF ₃ Et HHH Cl 0
SOCF ₃ Et H OMe HH 0 SOCF ₃ Et HHH Cl 1
SOCF ₃ Et H OMe HH 1 SOCF ₃ Et HHH Cl 2
SOCF ₃ Et H OMe HH 2 SOCF ₃ Et HHH Br 0
SOCF ₃ Et H OCF ₃ HH 0 SOCF ₃ Et HHH Br 1
SOCF ₃ Et H OCF ₃ HH 1 SOCF ₃ Et HHH Br 2
SOCF ₃ Et H OCF ₃ HH 2 SOCF ₃ Et HHHI 0
SOCF ₃ Et H NO ₂ HH 0 SOCF ₃ Et HHHI 1
――――――――――――――――――― ――――――――――――――――――――
Continuation of [Table 1] Continuation of [Table 1]
――――――――――――――――――― ――――――――――――――――――――
W1 R ¹ Y1 Y2 Y3 Y4 n W1 R ¹ Y1 Y2 Y3 Y4 n
――――――――――――――――――― ――――――――――――――――――――
SOCF ₃ Et HHHI 2 SOCF ₃ Et H Cl HI 0
SOCF ₃ Et HHH Me 0 SOCF ₃ Et H Cl HI 1
SOCF ₃ Et HHH Me 1 SOCF ₃ Et H Cl HI 2
SOCF ₃ Et HHH Me 2 SOCF ₃ Et H Br HF 0
SOCF ₃ Et HHH CF ₃ 0 SOCF ₃ Et H Br HF 1
SOCF ₃ Et HHH CF ₃ 1 SOCF ₃ Et H Br HF 2
SOCF ₃ Et HHH CF ₃ 2 SOCF ₃ Et H Br H Cl 0
SOCF ₃ Et HHH CF ₂ CF ₃ 0 SOCF ₃ Et H Br H Cl 1
SOCF ₃ Et HHH CF ₂ CF ₃ 1 SOCF ₃ Et H Br H Cl 2
SOCF ₃ Et HHH CF ₂ CF ₃ 2 SOCF ₃ Et H Br HI 0
SOCF ₃ Et HHH CF(CF ₃ ) ₂ 0 SOCF ₃ Et H Br HI 1
SOCF ₃ Et HHH CF(CF ₃ ) ₂ 1 SOCF ₃ Et H Br HI 2
SOCF ₃ Et HHH CF(CF ₃ ) ₂ 2 SOCF ₃ Et HIHF 0
SOCF ₃ Et HHH SMe 0 SOCF ₃ Et HIHF 1
SOCF ₃ Et HHH SMe 1 SOCF ₃ Et HIHF 2
SOCF ₃ Et HHH SMe 2 SOCF ₃ Et HIH Cl 0
SOCF ₃ Et HHH SOMe 0 SOCF ₃ Et HIH Cl 1
SOCF ₃ Et HHH SOMe 1 SOCF ₃ Et HIH Cl 2
SOCF ₃ Et HHH SOMe 2 SOCF ₃ Et HIH Br 0
SOCF ₃ Et HHH SO ₂ Me 0 SOCF ₃ Et HIH Br 1
SOCF ₃ Et HHH SO ₂ Me 1 SOCF ₃ Et HIH Br 2
SOCF ₃ Et HHH SO ₂ Me 2 SOCF ₃ Et HFH CN 0
SOCF ₃ Et HHH OMe 0 SOCF ₃ Et HFH CN 1
SOCF ₃ Et HHH OMe 1 SOCF ₃ Et HFH CN 2
SOCF ₃ Et HHH OMe 2 SOCF ₃ Et H Cl H CN 0
SOCF ₃ Et HHH OCF ₃ 0 SOCF ₃ Et H Cl H CN 1
SOCF ₃ Et HHH OCF ₃ 1 SOCF ₃ Et H Cl H CN 2
SOCF ₃ Et HHH OCF ₃ 2 SOCF ₃ Et H Br H CN 0
――――――――――――――――――― ――――――――――――――――――――
Continuation of [Table 1] Continuation of [Table 1]
――――――――――――――――――― ――――――――――――――――――――
W1 R ¹ Y1 Y2 Y3 Y4 n W1 R ¹ Y1 Y2 Y3 Y4 n
――――――――――――――――――― ――――――――――――――――――――
SOCF ₃ Et HHH NO ₂ 0 SOCF ₃ Et H Br H CN 1
SOCF ₃ Et HHH NO ₂ 1 SOCF ₃ Et H Br H CN 2
SOCF ₃ Et HHH NO ₂ 2 SOCF ₃ Et HIH CN 0
SOCF ₃ Et HHH CN 0 SOCF ₃ Et HIH CN 1
SOCF ₃ Et HHH CN 1 SOCF ₃ Et HIH CN 2
SOCF ₃ Et HHH CN 2 SOCF ₃ Et H CF ₃ HF 0
SOCF ₃ Et HFHF 0 SOCF ₃ Et H CF ₃ HF 1
SOCF ₃ Et HFHF 1 SOCF ₃ Et H CF ₃ HF 2
SOCF ₃ Et HFHF 2 SOCF ₃ Et H CF ₃ H Cl 0
SOCF ₃ Et H Cl H Cl 0 SOCF ₃ Et H CF ₃ H Cl 1
SOCF ₃ Et H Cl H Cl 1 SOCF ₃ Et H CF ₃ H Cl 2
SOCF ₃ Et H Cl H Cl 2 SOCF ₃ Et H CF ₃ H Br 0
SOCF ₃ Et H Br H Br 0 SOCF ₃ Et H CF ₃ H Br 1
SOCF ₃ Et H Br H Br 1 SOCF ₃ Et H CF ₃ H Br 2
SOCF ₃ Et H Br H Br 2 SOCF ₃ Et H CF ₃ HI 0
SOCF ₃ Et HIHI 0 SOCF ₃ Et H CF ₃ HI 1
SOCF ₃ Et HIHI 1 SOCF ₃ Et H CF ₃ HI 2
SOCF ₃ Et HIHI 2 SOCF ₃ Et H CF ₃ H CN 0
SOCF ₃ Et HFH Cl 0 SOCF ₃ Et H CF ₃ H CN 1
SOCF ₃ Et HFH Cl 1 SOCF ₃ Et H CF ₃ H CN 2
SOCF ₃ Et HFH Cl 2 SOCF ₃ Et HFFH 0
SOCF ₃ Et HFH Br 0 SOCF ₃ Et HFFH 1
SOCF ₃ Et HFH Br 1 SOCF ₃ Et HFFH 2
SOCF ₃ Et HFH Br 2 SOCF ₃ Et H Cl Cl H 0
SOCF ₃ Et HFHI 0 SOCF ₃ Et H Cl Cl H 1
SOCF ₃ Et HFHI 1 SOCF ₃ Et H Cl Cl H 2
SOCF ₃ Et HFHI 2 SOCF ₃ Et H Br Br H 0
SOCF ₃ Et H Cl HF 0 SOCF ₃ Et H Br Br H 1
SOCF ₃ Et H Cl HF 1 SOCF ₃ Et H Br Br H 2
SOCF ₃ Et H Cl HF 2 SOCF ₃ Et HIIH 0
SOCF ₃ Et H Cl H Br 0 SOCF ₃ Et HIIH 1
SOCF ₃ Et H Cl H Br 1 SOCF ₃ Et HIIH 2
SOCF ₃ Et H Cl H Br 2 SOCF ₃ Et HF Cl H 0
――――――――――――――――――― ――――――――――――――――――――
Continuation of [Table 1] Continuation of [Table 1]
――――――――――――――――――― ――――――――――――――――――――
W1 R ¹ Y1 Y2 Y3 Y4 n W1 R ¹ Y1 Y2 Y3 Y4 n
――――――――――――――――――― ――――――――――――――――――――
SOCF ₃ Et HF Cl H 1 SO ₂ CF ₃ Et HHHH 0
SOCF ₃ Et HF Cl H 2 SO ₂ CF ₃ Et HHHH 1
SOCF ₃ Et HF Br H 0 SO ₂ CF ₃ Et HHHH 2
SOCF ₃ Et HF Br H 1 SO ₂ CF ₃ Et FHHH 0
SOCF ₃ Et HF Br H 2 SO ₂ CF ₃ Et FHHH 1
SOCF ₃ Et HFIH 0 SO ₂ CF ₃ Et FHHH 2
SOCF ₃ Et HFIH 1 SO ₂ CF ₃ Et Cl HHH 0
SOCF ₃ Et HFIH 2 SO ₂ CF ₃ Et Cl HHH 1
SOCF ₃ Et H Cl FH 0 SO ₂ CF ₃ Et Cl HHH 2
SOCF ₃ Et H Cl FH 1 SO ₂ CF ₃ Et Br HHH 0
SOCF ₃ Et H Cl FH 2 SO ₂ CF ₃ Et Br HHH 1
SOCF ₃ Et H Cl Br H 0 SO ₂ CF ₃ Et Br HHH 2
SOCF ₃ Et H Cl Br H 1 SO ₂ CF ₃ Et IHHH 0
SOCF ₃ Et H Cl Br H 2 SO ₂ CF ₃ Et IHHH 1
SOCF ₃ Et H Cl IH 0 SO ₂ CF ₃ Et IHHH 2
SOCF ₃ Et H Cl IH 1 SO ₂ CF ₃ Et Me HHH 0
SOCF ₃ Et H Cl IH 2 SO ₂ CF ₃ Et Me HHH 1
SOCF ₃ Et H Br FH 0 SO ₂ CF ₃ Et Me HHH 2
SOCF ₃ Et H Br FH 1 SO ₂ CF ₃ Et CF ₃ HHH 0
SOCF ₃ Et H Br FH 2 SO ₂ CF ₃ Et CF ₃ HHH 1
SOCF ₃ Et H Br Cl H 0 SO ₂ CF ₃ Et CF ₃ HHH 2
SOCF ₃ Et H Br Cl H 1 SO ₂ CF ₃ Et HFHH 0
SOCF ₃ Et H Br Cl H 2 SO ₂ CF ₃ Et HFHH 1
――――――――――――――――――― ――――――――――――――――――――
Continuation of [Table 1] Continuation of [Table 1]
――――――――――――――――――― ――――――――――――――――――――
W1 R ¹ Y1 Y2 Y3 Y4 n W1 R ¹ Y1 Y2 Y3 Y4 n
――――――――――――――――――― ――――――――――――――――――――
SOCF ₃ Et H Br IH 0 SO ₂ CF ₃ Et HFHH 2
SOCF ₃ Et H Br IH 1 SO ₂ CF ₃ Et H Cl HH 0
SOCF ₃ Et H Br IH 2 SO ₂ CF ₃ Et H Cl HH 1
SOCF ₃ Et HIFH 0 SO ₂ CF ₃ Et H Cl HH 2
SOCF ₃ Et HIFH 1 SO ₂ CF ₃ Et H Br HH 0
SOCF ₃ Et HIFH 2 SO ₂ CF ₃ Et H Br HH 1
SOCF ₃ Et HI Cl H 0 SO ₂ CF ₃ Et H Br HH 2
SOCF ₃ Et HI Cl H 1 SO ₂ CF ₃ Et HIHH 0
SOCF ₃ Et HI Cl H 2 SO ₂ CF ₃ Et HIHH 1
SOCF ₃ Et HI Br H 0 SO ₂ CF ₃ Et HIHH 2
SOCF ₃ Et HI Br H 1 SO ₂ CF ₃ Et H Me HH 0
SOCF ₃ Et HI Br H 2 SO ₂ CF ₃ Et H Me HH 1
SOCF ₃ Et HF CN H 0 SO ₂ CF ₃ Et H Me HH 2
SOCF ₃ Et HF CN H 1 SO ₂ CF ₃ Et H CF ₃ HH 0
SOCF ₃ Et HF CN H 2 SO ₂ CF ₃ Et H CF ₃ HH 1
SOCF ₃ Et H Cl CN H 0 SO ₂ CF ₃ Et H CF ₃ HH 2
SOCF ₃ Et H Cl CN H 1 SO ₂ CF ₃ Et H CF ₂ CF ₃ HH 0
SOCF ₃ Et H Cl CN H 2 SO ₂ CF ₃ Et H CF ₂ CF ₃ HH 1
SOCF ₃ Et H Br CN H 0 SO ₂ CF ₃ Et H CF ₂ CF ₃ HH 2
SOCF ₃ Et H Br CN H 1 SO ₂ CF ₃ Et H CF(CF ₃ ) ₂ HH 0
SOCF ₃ Et H Br CN H 2 SO ₂ CF ₃ Et H CF(CF ₃ ) ₂ HH 1
SOCF ₃ Et HI CN H 0 SO ₂ CF ₃ Et H CF(CF ₃ ) ₂ HH 2
SOCF ₃ Et HI CN H 1 SO ₂ CF ₃ Et H SMe HH 0
SOCF ₃ Et HI CN H 2 SO ₂ CF ₃ Et H SMe HH 1
SOCF ₃ Et H CF ₃ FH 0 SO ₂ CF ₃ Et H SMe HH 2
SOCF ₃ Et H CF ₃ FH 1 SO ₂ CF ₃ Et H SOMe HH 0
SOCF ₃ Et H CF ₃ FH 2 SO ₂ CF ₃ Et H SOMe HH 1
SOCF ₃ Et H CF ₃ Cl H 0 SO ₂ CF ₃ Et H SOMe HH 2
SOCF ₃ Et H CF ₃ Cl H 1 SO ₂ CF ₃ Et H SO ₂ Me HH 0
SOCF ₃ Et H CF ₃ Cl H 2 SO ₂ CF ₃ Et H SO ₂ Me HH 1
SOCF ₃ Et H CF ₃ Br H 0 SO ₂ CF ₃ Et H SO ₂ Me HH 2
SOCF ₃ Et H CF ₃ Br H 1 SO ₂ CF ₃ Et H OMe HH 0
SOCF ₃ Et H CF ₃ Br H 2 SO ₂ CF ₃ Et H OMe HH 1
SOCF ₃ Et H CF ₃ IH 0 SO ₂ CF ₃ Et H OMe HH 2
SOCF ₃ Et H CF ₃ IH 1 SO ₂ CF ₃ Et H OCF ₃ HH 0
SOCF ₃ Et H CF ₃ IH 2 SO ₂ CF ₃ Et H OCF ₃ HH 1
SOCF ₃ Et H CF ₃ CN H 0 SO ₂ CF ₃ Et H OCF ₃ HH 2
SOCF ₃ Et H CF ₃ CN H 1 SO ₂ CF ₃ Et H NO ₂ HH 0
SOCF ₃ Et H CF ₃ CN H 2 ――――――――――――――――――――――
―――――――――――――――――――
Continuation of [Table 1] Continuation of [Table 1]
――――――――――――――――――― ――――――――――――――――――――
W1 R ¹ Y1 Y2 Y3 Y4 n W1 R ¹ Y1 Y2 Y3 Y4 n
――――――――――――――――――― ――――――――――――――――――――
SO ₂ CF ₃ Et H NO ₂ HH 1 SO ₂ CF ₃ Et HHHI 2
SO ₂ CF ₃ Et H NO ₂ HH 2 SO ₂ CF ₃ Et HHH Me 0
SO ₂ CF ₃ Et H CN HH 0 SO ₂ CF ₃ Et HHH Me 1
SO ₂ CF ₃ Et H CN HH 1 SO ₂ CF ₃ Et HHH Me 2
SO ₂ CF ₃ Et H CN HH 2 SO ₂ CF ₃ Et HHH CF ₃ 0
SO ₂ CF ₃ Et HHFH 0 SO ₂ CF ₃ Et HHH CF ₃ 1
SO ₂ CF ₃ Et HHFH 1 SO ₂ CF ₃ Et HHH CF ₃ 2
SO ₂ CF ₃ Et HHFH 2 SO ₂ CF ₃ Et HHH CF ₂ CF ₃ 0
SO ₂ CF ₃ Et HH Cl H 0 SO ₂ CF ₃ Et HHH CF ₂ CF ₃ 1
SO ₂ CF ₃ Et HH Cl H 1 SO ₂ CF ₃ Et HHH CF ₂ CF ₃ 2
SO ₂ CF ₃ Et HH Cl H 2 SO ₂ CF ₃ Et HHH CF(CF ₃ ) ₂ 0
SO ₂ CF ₃ Et HH Br H 0 SO ₂ CF ₃ Et HHH CF(CF ₃ ) ₂ 1
SO ₂ CF ₃ Et HH Br H 1 SO ₂ CF ₃ Et HHH CF(CF ₃ ) ₂ 2
SO ₂ CF ₃ Et HH Br H 2 SO ₂ CF ₃ Et HHH SMe 0
SO ₂ CF ₃ Et HHIH 0 SO ₂ CF ₃ Et HHH SMe 1
SO ₂ CF ₃ Et HHIH 1 SO ₂ CF ₃ Et HHH SMe 2
SO ₂ CF ₃ Et HHIH 2 SO ₂ CF ₃ Et HHH SOMe 0
SO ₂ CF ₃ Et HH Me H 0 SO ₂ CF ₃ Et HHH SOMe 1
SO ₂ CF ₃ Et HH Me H 1 SO ₂ CF ₃ Et HHH SOMe 2
SO ₂ CF ₃ Et HH Me H 2 SO ₂ CF ₃ Et HHH SO ₂ Me 0
SO ₂ CF ₃ Et HH CF ₃ H 0 SO ₂ CF ₃ Et HHH SO ₂ Me 1
SO ₂ CF ₃ Et HH CF ₃ H 1 SO ₂ CF ₃ Et HHH SO ₂ Me 2
SO ₂ CF ₃ Et HH CF ₃ H 2 SO ₂ CF ₃ Et HHH OMe 0
SO ₂ CF ₃ Et HH CF ₂ CF ₃ H 0 SO ₂ CF ₃ Et HHH OMe 1
SO ₂ CF ₃ Et HH CF ₂ CF ₃ H 1 SO ₂ CF ₃ Et HHH OMe 2
SO ₂ CF ₃ Et HH CF ₂ CF ₃ H 2 SO ₂ CF ₃ Et HHH OCF ₃ 0
SO ₂ CF ₃ Et HH CF(CF ₃ ) ₂ H 0 SO ₂ CF ₃ Et HHH OCF ₃ 1
SO ₂ CF ₃ Et HH CF(CF ₃ ) ₂ H 1 SO ₂ CF ₃ Et HHH OCF ₃ 2
SO ₂ CF ₃ Et HH CF(CF ₃ ) ₂ H 2 SO ₂ CF ₃ Et HHH NO ₂ 0
――――――――――――――――――― ――――――――――――――――――――
Continuation of [Table 1] Continuation of [Table 1]
――――――――――――――――――― ――――――――――――――――――――
W1 R ¹ Y1 Y2 Y3 Y4 n W1 R ¹ Y1 Y2 Y3 Y4 n
――――――――――――――――――― ――――――――――――――――――――
SO ₂ CF ₃ Et HH SMe H 0 SO ₂ CF ₃ Et HHH NO ₂ 1
SO ₂ CF ₃ Et HH SMe H 1 SO ₂ CF ₃ Et HHH NO ₂ 2
SO ₂ CF ₃ Et HH SMe H 2 SO ₂ CF ₃ Et HHH CN 0
SO ₂ CF ₃ Et HH SOMe H 0 SO ₂ CF ₃ Et HHH CN 1
SO ₂ CF ₃ Et HH SOMe H 1 SO ₂ CF ₃ Et HHH CN 2
SO ₂ CF ₃ Et HH SOMe H 2 SO ₂ CF ₃ Et HFHF 0
SO ₂ CF ₃ Et HH SO ₂ Me H 0 SO ₂ CF ₃ Et HFHF 1
SO ₂ CF ₃ Et HH SO ₂ Me H 1 SO ₂ CF ₃ Et HFHF 2
SO ₂ CF ₃ Et HH SO ₂ Me H 2 SO ₂ CF ₃ Et H Cl H Cl 0
SO ₂ CF ₃ Et HH OMe H 0 SO ₂ CF ₃ Et H Cl H Cl 1
SO ₂ CF ₃ Et HH OMe H 1 SO ₂ CF ₃ Et H Cl H Cl 2
SO ₂ CF ₃ Et HH OMe H 2 SO ₂ CF ₃ Et H Br H Br 0
SO ₂ CF ₃ Et HH OCF ₃ H 0 SO ₂ CF ₃ Et H Br H Br 1
SO ₂ CF ₃ Et HH OCF ₃ H 1 SO ₂ CF ₃ Et H Br H Br 2
SO ₂ CF ₃ Et HH OCF ₃ H 2 SO ₂ CF ₃ Et HIHI 0
SO ₂ CF ₃ Et HH NO ₂ H 0 SO ₂ CF ₃ Et HIHI 1
SO ₂ CF ₃ Et HH NO ₂ H 1 SO ₂ CF ₃ Et HIHI 2
SO ₂ CF ₃ Et HH NO ₂ H 2 SO ₂ CF ₃ Et HFH Cl 0
SO ₂ CF ₃ Et HH CN H 0 SO ₂ CF ₃ Et HFH Cl 1
SO ₂ CF ₃ Et HH CN H 1 SO ₂ CF ₃ Et HFH Cl 2
SO ₂ CF ₃ Et HH CN H 2 SO ₂ CF ₃ Et HFH Br 0
SO ₂ CF ₃ Et HHHF 0 SO ₂ CF ₃ Et HFH Br 1
SO ₂ CF ₃ Et HHHF 1 SO ₂ CF ₃ Et HFH Br 2
SO ₂ CF ₃ Et HHHF 2 SO ₂ CF ₃ Et HFHI 0
SO ₂ CF ₃ Et HHH Cl 0 SO ₂ CF ₃ Et HFHI 1
SO ₂ CF ₃ Et HHH Cl 1 SO ₂ CF ₃ Et HFHI 2
SO ₂ CF ₃ Et HHH Cl 2 SO ₂ CF ₃ Et H Cl HF 0
SO ₂ CF ₃ Et HHH Br 0 SO ₂ CF ₃ Et H Cl HF 1
SO ₂ CF ₃ Et HHH Br 1 SO ₂ CF ₃ Et H Cl HF 2
SO ₂ CF ₃ Et HHH Br 2 SO ₂ CF ₃ Et H Cl H Br 0
SO ₂ CF ₃ Et HHHI 0 SO ₂ CF ₃ Et H Cl H Br 1
SO ₂ CF ₃ Et HHHI 1 SO ₂ CF ₃ Et H Cl H Br 2
――――――――――――――――――― ――――――――――――――――――――
Continuation of [Table 1] Continuation of [Table 1]
――――――――――――――――――― ――――――――――――――――――――
W1 R ¹ Y1 Y2 Y3 Y4 n W1 R ¹ Y1 Y2 Y3 Y4 n
――――――――――――――――――― ――――――――――――――――――――
SO ₂ CF ₃ Et H Cl HI 0 SO ₂ CF ₃ Et HF Cl H 1
SO ₂ CF ₃ Et H Cl HI 1 SO ₂ CF ₃ Et HF Cl H 2
SO ₂ CF ₃ Et H Cl HI 2 SO ₂ CF ₃ Et HF Br H 0
SO ₂ CF ₃ Et H Br HF 0 SO ₂ CF ₃ Et HF Br H 1
SO ₂ CF ₃ Et H Br HF 1 SO ₂ CF ₃ Et HF Br H 2
SO ₂ CF ₃ Et H Br HF 2 SO ₂ CF ₃ Et HFIH 0
SO ₂ CF ₃ Et H Br H Cl 0 SO ₂ CF ₃ Et HFIH 1
SO ₂ CF ₃ Et H Br H Cl 1 SO ₂ CF ₃ Et HFIH 2
SO ₂ CF ₃ Et H Br H Cl 2 SO ₂ CF ₃ Et H Cl FH 0
SO ₂ CF ₃ Et H Br HI 0 SO ₂ CF ₃ Et H Cl FH 1
SO ₂ CF ₃ Et H Br HI 1 SO ₂ CF ₃ Et H Cl FH 2
SO ₂ CF ₃ Et H Br HI 2 SO ₂ CF ₃ Et H Cl Br H 0
SO ₂ CF ₃ Et HIHF 0 SO ₂ CF ₃ Et H Cl Br H 1
SO ₂ CF ₃ Et HIHF 1 SO ₂ CF ₃ Et H Cl Br H 2
SO ₂ CF ₃ Et HIHF 2 SO ₂ CF ₃ Et H Cl IH 0
SO ₂ CF ₃ Et HIH Cl 0 SO ₂ CF ₃ Et H Cl IH 1
SO ₂ CF ₃ Et HIH Cl 1 SO ₂ CF ₃ Et H Cl IH 2
SO ₂ CF ₃ Et HIH Cl 2 SO ₂ CF ₃ Et H Br FH 0
SO ₂ CF ₃ Et HIH Br 0 SO ₂ CF ₃ Et H Br FH 1
SO ₂ CF ₃ Et HIH Br 1 SO ₂ CF ₃ Et H Br FH 2
SO ₂ CF ₃ Et HIH Br 2 SO ₂ CF ₃ Et H Br Cl H 0
SO ₂ CF ₃ Et HFH CN 0 SO ₂ CF ₃ Et H Br Cl H 1
SO ₂ CF ₃ Et HFH CN 1 SO ₂ CF ₃ Et H Br Cl H 2
SO ₂ CF ₃ Et HFH CN 2 SO ₂ CF ₃ Et H Br IH 0
SO ₂ CF ₃ Et H Cl H CN 0 SO ₂ CF ₃ Et H Br IH 1
SO ₂ CF ₃ Et H Cl H CN 1 SO ₂ CF ₃ Et H Br IH 2
SO ₂ CF ₃ Et H Cl H CN 2 SO ₂ CF ₃ Et HIFH 0
SO ₂ CF ₃ Et H Br H CN 0 SO ₂ CF ₃ Et HIFH 1
SO ₂ CF ₃ Et H Br H CN 1 SO ₂ CF ₃ Et HIFH 2
SO ₂ CF ₃ Et H Br H CN 2 SO ₂ CF ₃ Et HI Cl H 0
SO ₂ CF ₃ Et HIH CN 0 SO ₂ CF ₃ Et HI Cl H 1
SO ₂ CF ₃ Et HIH CN 1 SO ₂ CF ₃ Et HI Cl H 2
SO ₂ CF ₃ Et HIH CN 2 SO ₂ CF ₃ Et HI Br H 0
――――――――――――――――――― ――――――――――――――――――――
Continuation of [Table 1] Continuation of [Table 1]
――――――――――――――――――― ――――――――――――――――――――
W1 R ¹ Y1 Y2 Y3 Y4 n W1 R ¹ Y1 Y2 Y3 Y4 n
――――――――――――――――――― ――――――――――――――――――――
SO ₂ CF ₃ Et H CF ₃ HF 0 SO ₂ CF ₃ Et HI Br H 1
SO ₂ CF ₃ Et H CF ₃ HF 1 SO ₂ CF ₃ Et HI Br H 2
SO ₂ CF ₃ Et H CF ₃ HF 2 SO ₂ CF ₃ Et HF CN H 0
SO ₂ CF ₃ Et H CF ₃ H Cl 0 SO ₂ CF ₃ Et HF CN H 1
SO ₂ CF ₃ Et H CF ₃ H Cl 1 SO ₂ CF ₃ Et HF CN H 2
SO ₂ CF ₃ Et H CF ₃ H Cl 2 SO ₂ CF ₃ Et H Cl CN H 0
SO ₂ CF ₃ Et H CF ₃ H Br 0 SO ₂ CF ₃ Et H Cl CN H 1
SO ₂ CF ₃ Et H CF ₃ H Br 1 SO ₂ CF ₃ Et H Cl CN H 2
SO ₂ CF ₃ Et H CF ₃ H Br 2 SO ₂ CF ₃ Et H Br CN H 0
SO ₂ CF ₃ Et H CF ₃ HI 0 SO ₂ CF ₃ Et H Br CN H 1
SO ₂ CF ₃ Et H CF ₃ HI 1 SO ₂ CF ₃ Et H Br CN H 2
SO ₂ CF ₃ Et H CF ₃ HI 2 SO ₂ CF ₃ Et HI CN H 0
SO ₂ CF ₃ Et H CF ₃ H CN 0 SO ₂ CF ₃ Et HI CN H 1
SO ₂ CF ₃ Et H CF ₃ H CN 1 SO ₂ CF ₃ Et HI CN H 2
SO ₂ CF ₃ Et H CF ₃ H CN 2 SO ₂ CF ₃ Et H CF ₃ FH 0
SO ₂ CF ₃ Et HFFH 0 SO ₂ CF ₃ Et H CF ₃ FH 1
SO ₂ CF ₃ Et HFFH 1 SO ₂ CF ₃ Et H CF ₃ FH 2
SO ₂ CF ₃ Et HFFH 2 SO ₂ CF ₃ Et H CF ₃ Cl H 0
SO ₂ CF ₃ Et H Cl Cl H 0 SO ₂ CF ₃ Et H CF ₃ Cl H 1
SO ₂ CF ₃ Et H Cl Cl H 1 SO ₂ CF ₃ Et H CF ₃ Cl H 2
SO ₂ CF ₃ Et H Cl Cl H 2 SO ₂ CF ₃ Et H CF ₃ Br H 0
SO ₂ CF ₃ Et H Br Br H 0 SO ₂ CF ₃ Et H CF ₃ Br H 1
SO ₂ CF ₃ Et H Br Br H 1 SO ₂ CF ₃ Et H CF ₃ Br H 2
SO ₂ CF ₃ Et H Br Br H 2 SO ₂ CF ₃ Et H CF ₃ IH 0
SO ₂ CF ₃ Et HIIH 0 SO ₂ CF ₃ Et H CF ₃ IH 1
SO ₂ CF ₃ Et HIIH 1 SO ₂ CF ₃ Et H CF ₃ IH 2
SO ₂ CF ₃ Et HIIH 2 SO ₂ CF ₃ Et H CF ₃ CN H 0
SO ₂ CF ₃ Et HF Cl H 0 SO ₂ CF ₃ Et H CF ₃ CN H 1
――――――――――――――――――― SO ₂ CF ₃ Et H CF ₃ CN H 2
――――――――――――――――――――
[Table 2]

Continuation of [Table 2] Continuation of [Table 2]
――――――――――――――――――― ―――――――――――――――――――
W1 R ¹ Y1 Y2 Y3 Y4 n W1 R ¹ Y1 Y2 Y3 Y4 n
――――――――――――――――――― ―――――――――――――――――――
CF ₃ Et HHHH 0 CF ₃ Et HIHH 1
CF ₃ Et HHHH 1 CF ₃ Et HIHH 2
CF ₃ Et HHHH 2 CF ₃ Et H Me HH 0
CF ₃ Et FHHH 0 CF ₃ Et H Me HH 1
CF ₃ Et FHHH 1 CF ₃ Et H Me HH 2
CF ₃ Et FHHH 2 CF ₃ Et H CF ₃ HH 0
CF ₃ Et Cl HHH 0 CF ₃ Et H CF ₃ HH 1
CF ₃ Et Cl HHH 1 CF ₃ Et H CF ₃ HH 2
CF ₃ Et Cl HHH 2 CF ₃ Et H CF ₂ CF ₃ HH 0
CF ₃ Et Br HHH 0 CF ₃ Et H CF ₂ CF ₃ HH 1
CF ₃ Et Br HHH 1 CF ₃ Et H CF ₂ CF ₃ HH 2
CF ₃ Et Br HHH 2 CF ₃ Et H CF(CF ₃ ) ₂ HH 0
CF ₃ Et IHHH 0 CF ₃ Et H CF(CF ₃ ) ₂ HH 1
CF ₃ Et IHHH 1 CF ₃ Et H CF(CF ₃ ) ₂ HH 2
CF ₃ Et IHHH 2 CF ₃ Et H SMe HH 0
CF ₃ Et Me HHH 0 CF ₃ Et H SMe HH 1
CF ₃ Et Me HHH 1 CF ₃ Et H SMe HH 2
CF ₃ Et Me HHH 2 CF ₃ Et H SOMe HH 0
CF ₃ Et CF ₃ HHH 0 CF ₃ Et H SOMe HH 1
CF ₃ Et CF ₃ HHH 1 CF ₃ Et H SOMe HH 2
CF ₃ Et CF ₃ HHH 2 CF ₃ Et H SO ₂ Me HH 0
CF ₃ Et HFHH 0 CF ₃ Et H SO ₂ Me HH 1
CF ₃ Et HFHH 1 CF ₃ Et H SO ₂ Me HH 2
CF ₃ Et HFHH 2 CF ₃ Et H OMe HH 0
CF ₃ Et H Cl HH 0 CF ₃ Et H OMe HH 1
CF ₃ Et H Cl HH 1 CF ₃ Et H OMe HH 2
CF ₃ Et H Cl HH 2 CF ₃ Et H OCF ₃ HH 0
CF ₃ Et H Br HH 0 CF ₃ Et H OCF ₃ HH 1
CF ₃ Et H Br HH 1 CF ₃ Et H OCF ₃ HH 2
CF ₃ Et H Br HH 2 CF ₃ Et H NO ₂ HH 0
CF ₃ Et HIHH 0 ―――――――――――――――――――
―――――――――――――――――――
Continuation of [Table 2] Continuation of [Table 2]
――――――――――――――――――― ――――――――――――――――――――
W1 R ¹ Y1 Y2 Y3 Y4 n W1 R ¹ Y1 Y2 Y3 Y4 n
――――――――――――――――――― ――――――――――――――――――――
CF ₃ Et H NO ₂ HH 1 CF ₃ Et HHHI 2
CF ₃ Et H NO ₂ HH 2 CF ₃ Et HHH Me 0
CF ₃ Et H CN HH 0 CF ₃ Et HHH Me 1
CF ₃ Et H CN HH 1 CF ₃ Et HHH Me 2
CF ₃ Et H CN HH 2 CF ₃ Et HHH CF ₃ 0
CF ₃ Et HHFH 0 CF ₃ Et HHH CF ₃ 1
CF ₃ Et HHFH 1 CF ₃ Et HHH CF ₃ 2
CF ₃ Et HHFH 2 CF ₃ Et HHH CF ₂ CF ₃ 0
CF ₃ Et HH Cl H 0 CF ₃ Et HHH CF ₂ CF ₃ 1
CF ₃ Et HH Cl H 1 CF ₃ Et HHH CF ₂ CF ₃ 2
CF ₃ Et HH Cl H 2 CF ₃ Et HHH CF(CF ₃ ) ₂ 0
CF ₃ Et HH Br H 0 CF ₃ Et HHH CF(CF ₃ ) ₂ 1
CF ₃ Et HH Br H 1 CF ₃ Et HHH CF(CF ₃ ) ₂ 2
CF ₃ Et HH Br H 2 CF ₃ Et HHH SMe 0
CF ₃ Et HHIH 0 CF ₃ Et HHH SMe 1
CF ₃ Et HHIH 1 CF ₃ Et HHH SMe 2
CF ₃ Et HHIH 2 CF ₃ Et HHH SOMe 0
CF ₃ Et HH Me H 0 CF ₃ Et HHH SOMe 1
CF ₃ Et HH Me H 1 CF ₃ Et HHH SOMe 2
CF ₃ Et HH Me H 2 CF ₃ Et HHH SO ₂ Me 0
CF ₃ Et HH CF ₃ H 0 CF ₃ Et HHH SO ₂ Me 1
CF ₃ Et HH CF ₃ H 1 CF ₃ Et HHH SO ₂ Me 2
CF ₃ Et HH CF ₃ H 2 CF ₃ Et HHH OMe 0
CF ₃ Et HH CF ₂ CF ₃ H 0 CF ₃ Et HHH OMe 1
CF ₃ Et HH CF ₂ CF ₃ H 1 CF ₃ Et HHH OMe 2
CF ₃ Et HH CF ₂ CF ₃ H 2 CF ₃ Et HHH OCF ₃ 0
CF ₃ Et HH CF(CF ₃ ) ₂ H 0 CF ₃ Et HHH OCF ₃ 1
CF ₃ Et HH CF(CF ₃ ) ₂ H 1 CF ₃ Et HHH OCF ₃ 2
CF ₃ Et HH CF(CF ₃ ) ₂ H 2 CF ₃ Et HHH NO ₂ 0
CF ₃ Et HH SMe H 0 CF ₃ Et HHH NO ₂ 1
CF ₃ Et HH SMe H 1 CF ₃ Et HHH NO ₂ 2
CF ₃ Et HH SMe H 2 CF ₃ Et HHH CN 0
CF ₃ Et HH SOMe H 0 CF ₃ Et HHH CN 1
CF ₃ Et HH SOMe H 1 CF ₃ Et HHH CN 2
CF ₃ Et HH SOMe H 2 CF ₃ Et HFHF 0
CF ₃ Et HH SO ₂ Me H 0 CF ₃ Et HFHF 1
CF ₃ Et HH SO ₂ Me H 1 CF ₃ Et HFHF 2
CF ₃ Et HH SO ₂ Me H 2 CF ₃ Et H Cl H Cl 0
CF ₃ Et HH OMe H 0 CF ₃ Et H Cl H Cl 1
CF ₃ Et HH OMe H 1 CF ₃ Et H Cl H Cl 2
CF ₃ Et HH OMe H 2 CF ₃ Et H Br H Br 0
CF ₃ Et HH OCF ₃ H 0 CF ₃ Et H Br H Br 1
CF ₃ Et HH OCF ₃ H 1 CF ₃ Et H Br H Br 2
CF ₃ Et HH OCF ₃ H 2 CF ₃ Et HIHI 0
CF ₃ Et HH NO ₂ H 0 CF ₃ Et HIHI 1
CF ₃ Et HH NO ₂ H 1 CF ₃ Et HIHI 2
CF ₃ Et HH NO ₂ H 2 CF ₃ Et HFH Cl 0
CF ₃ Et HH CN H 0 CF ₃ Et HFH Cl 1
CF ₃ Et HH CN H 1 CF ₃ Et HFH Cl 2
CF ₃ Et HH CN H 2 CF ₃ Et HFH Br 0
CF ₃ Et HHHF 0 CF ₃ Et HFH Br 1
CF ₃ Et HHHF 1 CF ₃ Et HFH Br 2
CF ₃ Et HHHF 2 CF ₃ Et HFHI 0
CF ₃ Et HHH Cl 0 CF ₃ Et HFHI 1
CF ₃ Et HHH Cl 1 CF ₃ Et HFHI 2
CF ₃ Et HHH Cl 2 CF ₃ Et H Cl HF 0
CF ₃ Et HHH Br 0 CF ₃ Et H Cl HF 1
CF ₃ Et HHH Br 1 CF ₃ Et H Cl HF 2
CF ₃ Et HHH Br 2 CF ₃ Et H Cl H Br 0
CF ₃ Et HHHI 0 CF ₃ Et H Cl H Br 1
CF ₃ Et HHHI 1 CF ₃ Et H Cl H Br 2
――――――――――――――――――― ――――――――――――――――――――
Continuation of [Table 2] Continuation of [Table 2]
――――――――――――――――――― ――――――――――――――――――――
W1 R ¹ Y1 Y2 Y3 Y4 n W1 R ¹ Y1 Y2 Y3 Y4 n
――――――――――――――――――― ――――――――――――――――――――
CF ₃ Et H Cl HI 0 CF ₃ Et HF Cl H 1
CF ₃ Et H Cl HI 1 CF ₃ Et HF Cl H 2
CF ₃ Et H Cl HI 2 CF ₃ Et HF Br H 0
CF ₃ Et H Br HF 0 CF ₃ Et HF Br H 1
CF ₃ Et H Br HF 1 CF ₃ Et HF Br H 2
CF ₃ Et H Br HF 2 CF ₃ Et HFIH 0
CF ₃ Et H Br H Cl 0 CF ₃ Et HFIH 1
CF ₃ Et H Br H Cl 1 CF ₃ Et HFIH 2
CF ₃ Et H Br H Cl 2 CF ₃ Et H Cl FH 0
CF ₃ Et H Br HI 0 CF ₃ Et H Cl FH 1
CF ₃ Et H Br HI 1 CF ₃ Et H Cl FH 2
CF ₃ Et H Br HI 2 CF ₃ Et H Cl Br H 0
CF ₃ Et HIHF 0 CF ₃ Et H Cl Br H 1
CF ₃ Et HIHF 1 CF ₃ Et H Cl Br H 2
CF ₃ Et HIHF 2 CF ₃ Et H Cl IH 0
CF ₃ Et HIH Cl 0 CF ₃ Et H Cl IH 1
CF ₃ Et HIH Cl 1 CF ₃ Et H Cl IH 2
CF ₃ Et HIH Cl 2 CF ₃ Et H Br FH 0
CF ₃ Et HIH Br 0 CF ₃ Et H Br FH 1
CF ₃ Et HIH Br 1 CF ₃ Et H Br FH 2
CF ₃ Et HIH Br 2 CF ₃ Et H Br Cl H 0
CF ₃ Et HFH CN 0 CF ₃ Et H Br Cl H 1
CF ₃ Et HFH CN 1 CF ₃ Et H Br Cl H 2
CF ₃ Et HFH CN 2 CF ₃ Et H Br IH 0
CF ₃ Et H Cl H CN 0 CF ₃ Et H Br IH 1
CF ₃ Et H Cl H CN 1 CF ₃ Et H Br IH 2
CF ₃ Et H Cl H CN 2 CF ₃ Et HIFH 0
CF ₃ Et H Br H CN 0 CF ₃ Et HIFH 1
CF ₃ Et H Br H CN 1 CF ₃ Et HIFH 2
CF ₃ Et H Br H CN 2 CF ₃ Et HI Cl H 0
CF ₃ Et HIH CN 0 CF ₃ Et HI Cl H 1
CF ₃ Et HIH CN 1 CF ₃ Et HI Cl H 2
CF ₃ Et HIH CN 2 CF ₃ Et HI Br H 0
――――――――――――――――――― ――――――――――――――――――――
Continuation of [Table 2] Continuation of [Table 2]
――――――――――――――――――― ――――――――――――――――――――
W1 R ¹ Y1 Y2 Y3 Y4 n W1 R ¹ Y1 Y2 Y3 Y4 n
――――――――――――――――――― ――――――――――――――――――――
CF ₃ Et H CF ₃ HF 0 CF ₃ Et HI Br H 1
CF ₃ Et H CF ₃ HF 1 CF ₃ Et HI Br H 2
CF ₃ Et H CF ₃ HF 2 CF ₃ Et HF CN H 0
CF ₃ Et H CF ₃ H Cl 0 CF ₃ Et HF CN H 1
CF ₃ Et H CF ₃ H Cl 1 CF ₃ Et HF CN H 2
CF ₃ Et H CF ₃ H Cl 2 CF ₃ Et H Cl CN H 0
CF ₃ Et H CF ₃ H Br 0 CF ₃ Et H Cl CN H 1
CF ₃ Et H CF ₃ H Br 1 CF ₃ Et H Cl CN H 2
CF ₃ Et H CF ₃ H Br 2 CF ₃ Et H Br CN H 0
CF ₃ Et H CF ₃ HI 0 CF ₃ Et H Br CN H 1
CF ₃ Et H CF ₃ HI 1 CF ₃ Et H Br CN H 2
CF ₃ Et H CF ₃ HI 2 CF ₃ Et HI CN H 0
CF ₃ Et H CF ₃ H CN 0 CF ₃ Et HI CN H 1
CF ₃ Et H CF ₃ H CN 1 CF ₃ Et HI CN H 2
CF ₃ Et H CF ₃ H CN 2 CF ₃ Et H CF ₃ FH 0
CF ₃ Et HFFH 0 CF ₃ Et H CF ₃ FH 1
CF ₃ Et HFFH 1 CF ₃ Et H CF ₃ FH 2
CF ₃ Et HFFH 2 CF ₃ Et H CF ₃ Cl H 0
CF ₃ Et H Cl Cl H 0 CF ₃ Et H CF ₃ Cl H 1
CF ₃ Et H Cl Cl H 1 CF ₃ Et H CF ₃ Cl H 2
CF ₃ Et H Cl Cl H 2 CF ₃ Et H CF ₃ Br H 0
CF ₃ Et H Br Br H 0 CF ₃ Et H CF ₃ Br H 1
CF ₃ Et H Br Br H 1 CF ₃ Et H CF ₃ Br H 2
CF ₃ Et H Br Br H 2 CF ₃ Et H CF ₃ IH 0
CF ₃ Et HIIH 0 CF ₃ Et H CF ₃ IH 1
CF ₃ Et HIIH 1 CF ₃ Et H CF ₃ IH 2
CF ₃ Et HIIH 2 CF ₃ Et H CF ₃ CN H 0
CF ₃ Et HF Cl H 0 CF ₃ Et H CF ₃ CN H 1
――――――――――――――――――― CF ₃ Et H CF ₃ CN H 2
――――――――――――――――――――

Continuation of [Table 2] Continuation of [Table 2]
――――――――――――――――――― ――――――――――――――――――――
W1 R ¹ Y1 Y2 Y3 Y4 n W1 R ¹ Y1 Y2 Y3 Y4 n
――――――――――――――――――― ――――――――――――――――――――
CF ₂ CF ₃ Et HHHH 0 CF ₂ CF ₃ Et H NO ₂ HH 1
CF ₂ CF ₃ Et HHHH 1 CF ₂ CF ₃ Et H NO ₂ HH 2
CF ₂ CF ₃ Et HHHH 2 CF ₂ CF ₃ Et H CN HH 0
CF ₂ CF ₃ Et FHHH 0 CF ₂ CF ₃ Et H CN HH 1
CF ₂ CF ₃ Et FHHH 1 CF ₂ CF ₃ Et H CN HH 2
CF ₂ CF ₃ Et FHHH 2 CF ₂ CF ₃ Et HHFH 0
CF ₂ CF ₃ Et Cl HHH 0 CF ₂ CF ₃ Et HHFH 1
CF ₂ CF ₃ Et Cl HHH 1 CF ₂ CF ₃ Et HHFH 2
CF ₂ CF ₃ Et Cl HHH 2 CF ₂ CF ₃ Et HH Cl H 0
CF ₂ CF ₃ Et Br HHH 0 CF ₂ CF ₃ Et HH Cl H 1
CF ₂ CF ₃ Et Br HHH 1 CF ₂ CF ₃ Et HH Cl H 2
CF ₂ CF ₃ Et Br HHH 2 CF ₂ CF ₃ Et HH Br H 0
CF ₂ CF ₃ Et IHHH 0 CF ₂ CF ₃ Et HH Br H 1
CF ₂ CF ₃ Et IHHH 1 CF ₂ CF ₃ Et HH Br H 2
CF ₂ CF ₃ Et IHHH 2 CF ₂ CF ₃ Et HHIH 0
CF ₂ CF ₃ Et Me HHH 0 CF ₂ CF ₃ Et HHIH 1
CF ₂ CF ₃ Et Me HHH 1 CF ₂ CF ₃ Et HHIH 2
CF ₂ CF ₃ Et Me HHH 2 CF ₂ CF ₃ Et HH Me H 0
CF ₂ CF ₃ Et CF ₃ HHH 0 CF ₂ CF ₃ Et HH Me H 1
CF ₂ CF ₃ Et CF ₃ HHH 1 CF ₂ CF ₃ Et HH Me H 2
CF ₂ CF ₃ Et CF ₃ HHH 2 CF ₂ CF ₃ Et HH CF ₃ H 0
CF ₂ CF ₃ Et HFHH 0 CF ₂ CF ₃ Et HH CF ₃ H 1
CF ₂ CF ₃ Et HFHH 1 CF ₂ CF ₃ Et HH CF ₃ H 2
CF ₂ CF ₃ Et HFHH 2 CF ₂ CF ₃ Et HH CF ₂ CF ₃ H 0
――――――――――――――――――― ――――――――――――――――――――
Continuation of [Table 2] Continuation of [Table 2]
――――――――――――――――――― ――――――――――――――――――――
W1 R ¹ Y1 Y2 Y3 Y4 n W1 R ¹ Y1 Y2 Y3 Y4 n
――――――――――――――――――― ――――――――――――――――――――
CF ₂ CF ₃ Et H Cl HH 0 CF ₂ CF ₃ Et HH CF ₂ CF ₃ H 1
CF ₂ CF ₃ Et H Cl HH 1 CF ₂ CF ₃ Et HH CF ₂ CF ₃ H 2
CF ₂ CF ₃ Et H Cl HH 2 CF ₂ CF ₃ Et HH CF(CF ₃ ) ₂ H 0
CF ₂ CF ₃ Et H Br HH 0 CF ₂ CF ₃ Et HH CF(CF ₃ ) ₂ H 1
CF ₂ CF ₃ Et H Br HH 1 CF ₂ CF ₃ Et HH CF(CF ₃ ) ₂ H 2
CF ₂ CF ₃ Et H Br HH 2 CF ₂ CF ₃ Et HH SMe H 0
CF ₂ CF ₃ Et HIHH 0 CF ₂ CF ₃ Et HH SMe H 1
CF ₂ CF ₃ Et HIHH 1 CF ₂ CF ₃ Et HH SMe H 2
CF ₂ CF ₃ Et HIHH 2 CF ₂ CF ₃ Et HH SOMe H 0
CF ₂ CF ₃ Et H Me HH 0 CF ₂ CF ₃ Et HH SOMe H 1
CF ₂ CF ₃ Et H Me HH 1 CF ₂ CF ₃ Et HH SOMe H 2
CF ₂ CF ₃ Et H Me HH 2 CF ₂ CF ₃ Et HH SO ₂ Me H 0
CF ₂ CF ₃ Et H CF ₃ HH 0 CF ₂ CF ₃ Et HH SO ₂ Me H 1
CF ₂ CF ₃ Et H CF ₃ HH 1 CF ₂ CF ₃ Et HH SO ₂ Me H 2
CF ₂ CF ₃ Et H CF ₃ HH 2 CF ₂ CF ₃ Et HH OMe H 0
CF ₂ CF ₃ Et H CF ₂ CF ₃ HH 0 CF ₂ CF ₃ Et HH OMe H 1
CF ₂ CF ₃ Et H CF ₂ CF ₃ HH 1 CF ₂ CF ₃ Et HH OMe H 2
CF ₂ CF ₃ Et H CF ₂ CF ₃ HH 2 CF ₂ CF ₃ Et HH OCF ₃ H 0
CF ₂ CF ₃ Et H CF(CF ₃ ) ₂ HH 0 CF ₂ CF ₃ Et HH OCF ₃ H 1
CF ₂ CF ₃ Et H CF(CF ₃ ) ₂ HH 1 CF ₂ CF ₃ Et HH OCF ₃ H 2
CF ₂ CF ₃ Et H CF(CF ₃ ) ₂ HH 2 CF ₂ CF ₃ Et HH NO ₂ H 0
CF ₂ CF ₃ Et H SMe HH 0 CF ₂ CF ₃ Et HH NO ₂ H 1
CF ₂ CF ₃ Et H SMe HH 1 CF ₂ CF ₃ Et HH NO ₂ H 2
CF ₂ CF ₃ Et H SMe HH 2 CF ₂ CF ₃ Et HH CN H 0
CF ₂ CF ₃ Et H SOMe HH 0 CF ₂ CF ₃ Et HH CN H 1
CF ₂ CF ₃ Et H SOMe HH 1 CF ₂ CF ₃ Et HH CN H 2
CF ₂ CF ₃ Et H SOMe HH 2 CF ₂ CF ₃ Et HHHF 0
CF ₂ CF ₃ Et H SO ₂ Me HH 0 CF ₂ CF ₃ Et HHHF 1
CF ₂ CF ₃ Et H SO ₂ Me HH 1 CF ₂ CF ₃ Et HHHF 2
CF ₂ CF ₃ Et H SO ₂ Me HH 2 CF ₂ CF ₃ Et HHH Cl 0
CF ₂ CF ₃ Et H OMe HH 0 CF ₂ CF ₃ Et HHH Cl 1
CF ₂ CF ₃ Et H OMe HH 1 CF ₂ CF ₃ Et HHH Cl 2
CF ₂ CF ₃ Et H OMe HH 2 CF ₂ CF ₃ Et HHH Br 0
CF ₂ CF ₃ Et H OCF ₃ HH 0 CF ₂ CF ₃ Et HHH Br 1
CF ₂ CF ₃ Et H OCF ₃ HH 1 CF ₂ CF ₃ Et HHH Br 2
CF ₂ CF ₃ Et H OCF ₃ HH 2 CF ₂ CF ₃ Et HHHI 0
CF ₂ CF ₃ Et H NO ₂ HH 0 CF ₂ CF ₃ Et HHHI 1
――――――――――――――――――― ――――――――――――――――――――
Continuation of [Table 2] Continuation of [Table 2]
――――――――――――――――――― ――――――――――――――――――――
W1 R ¹ Y1 Y2 Y3 Y4 n W1 R ¹ Y1 Y2 Y3 Y4 n
――――――――――――――――――― ――――――――――――――――――――
CF ₂ CF ₃ Et HHHI 2 CF ₂ CF ₃ Et H Cl HI 0
CF ₂ CF ₃ Et HHH Me 0 CF ₂ CF ₃ Et H Cl HI 1
CF ₂ CF ₃ Et HHH Me 1 CF ₂ CF ₃ Et H Cl HI 2
CF ₂ CF ₃ Et HHH Me 2 CF ₂ CF ₃ Et H Br HF 0
CF ₂ CF ₃ Et HHH CF ₃ 0 CF ₂ CF ₃ Et H Br HF 1
CF ₂ CF ₃ Et HHH CF ₃ 1 CF ₂ CF ₃ Et H Br HF 2
CF ₂ CF ₃ Et HHH CF ₃ 2 CF ₂ CF ₃ Et H Br H Cl 0
CF ₂ CF ₃ Et HHH CF ₂ CF ₃ 0 CF ₂ CF ₃ Et H Br H Cl 1
CF ₂ CF ₃ Et HHH CF ₂ CF ₃ 1 CF ₂ CF ₃ Et H Br H Cl 2
CF ₂ CF ₃ Et HHH CF ₂ CF ₃ 2 CF ₂ CF ₃ Et H Br HI 0
CF ₂ CF ₃ Et HHH CF(CF ₃ ) ₂ 0 CF ₂ CF ₃ Et H Br HI 1
CF ₂ CF ₃ Et HHH CF(CF ₃ ) ₂ 1 CF ₂ CF ₃ Et H Br HI 2
CF ₂ CF ₃ Et HHH CF(CF ₃ ) ₂ 2 CF ₂ CF ₃ Et HIHF 0
CF ₂ CF ₃ Et HHH SMe 0 CF ₂ CF ₃ Et HIHF 1
CF ₂ CF ₃ Et HHH SMe 1 CF ₂ CF ₃ Et HIHF 2
CF ₂ CF ₃ Et HHH SMe 2 CF ₂ CF ₃ Et HIH Cl 0
CF ₂ CF ₃ Et HHH SOMe 0 CF ₂ CF ₃ Et HIH Cl 1
CF ₂ CF ₃ Et HHH SOMe 1 CF ₂ CF ₃ Et HIH Cl 2
CF ₂ CF ₃ Et HHH SOMe 2 CF ₂ CF ₃ Et HIH Br 0
CF ₂ CF ₃ Et HHH SO ₂ Me 0 CF ₂ CF ₃ Et HIH Br 1
CF ₂ CF ₃ Et HHH SO ₂ Me 1 CF ₂ CF ₃ Et HIH Br 2
CF ₂ CF ₃ Et HHH SO ₂ Me 2 CF ₂ CF ₃ Et HFH CN 0
CF ₂ CF ₃ Et HHH OMe 0 CF ₂ CF ₃ Et HFH CN 1
CF ₂ CF ₃ Et HHH OMe 1 CF ₂ CF ₃ Et HFH CN 2
CF ₂ CF ₃ Et HHH OMe 2 CF ₂ CF ₃ Et H Cl H CN 0
CF ₂ CF ₃ Et HHH OCF ₃ 0 CF ₂ CF ₃ Et H Cl H CN 1
CF ₂ CF ₃ Et HHH OCF ₃ 1 CF ₂ CF ₃ Et H Cl H CN 2
CF ₂ CF ₃ Et HHH OCF ₃ 2 CF ₂ CF ₃ Et H Br H CN 0
CF ₂ CF ₃ Et HHH NO ₂ 0 CF ₂ CF ₃ Et H Br H CN 1
CF ₂ CF ₃ Et HHH NO ₂ 1 CF ₂ CF ₃ Et H Br H CN 2
CF ₂ CF ₃ Et HHH NO ₂ 2 CF ₂ CF ₃ Et HIH CN 0
CF ₂ CF ₃ Et HHH CN 0 CF ₂ CF ₃ Et HIH CN 1
CF ₂ CF ₃ Et HHH CN 1 CF ₂ CF ₃ Et HIH CN 2
CF ₂ CF ₃ Et HHH CN 2 CF ₂ CF ₃ Et H CF ₃ HF 0
――――――――――――――――――― ――――――――――――――――――――
Continuation of [Table 2] Continuation of [Table 2]
――――――――――――――――――― ――――――――――――――――――――
W1 R ¹ Y1 Y2 Y3 Y4 n W1 R ¹ Y1 Y2 Y3 Y4 n
――――――――――――――――――― ――――――――――――――――――――
CF ₂ CF ₃ Et HFHF 0 CF ₂ CF ₃ Et H CF ₃ HF 1
CF ₂ CF ₃ Et HFHF 1 CF ₂ CF ₃ Et H CF ₃ HF 2
CF ₂ CF ₃ Et HFHF 2 CF ₂ CF ₃ Et H CF ₃ H Cl 0
CF ₂ CF ₃ Et H Cl H Cl 0 CF ₂ CF ₃ Et H CF ₃ H Cl 1
CF ₂ CF ₃ Et H Cl H Cl 1 CF ₂ CF ₃ Et H CF ₃ H Cl 2
CF ₂ CF ₃ Et H Cl H Cl 2 CF ₂ CF ₃ Et H CF ₃ H Br 0
CF ₂ CF ₃ Et H Br H Br 0 CF ₂ CF ₃ Et H CF ₃ H Br 1
CF ₂ CF ₃ Et H Br H Br 1 CF ₂ CF ₃ Et H CF ₃ H Br 2
CF ₂ CF ₃ Et H Br H Br 2 CF ₂ CF ₃ Et H CF ₃ HI 0
CF ₂ CF ₃ Et HIHI 0 CF ₂ CF ₃ Et H CF ₃ HI 1
CF ₂ CF ₃ Et HIHI 1 CF ₂ CF ₃ Et H CF ₃ HI 2
CF ₂ CF ₃ Et HIHI 2 CF ₂ CF ₃ Et H CF ₃ H CN 0
CF ₂ CF ₃ Et HFH Cl 0 CF ₂ CF ₃ Et H CF ₃ H CN 1
CF ₂ CF ₃ Et HFH Cl 1 CF ₂ CF ₃ Et H CF ₃ H CN 2
CF ₂ CF ₃ Et HFH Cl 2 CF ₂ CF ₃ Et HFFH 0
CF ₂ CF ₃ Et HFH Br 0 CF ₂ CF ₃ Et HFFH 1
CF ₂ CF ₃ Et HFH Br 1 CF ₂ CF ₃ Et HFFH 2
CF ₂ CF ₃ Et HFH Br 2 CF ₂ CF ₃ Et H Cl Cl H 0
CF ₂ CF ₃ Et HFHI 0 CF ₂ CF ₃ Et H Cl Cl H 1
CF ₂ CF ₃ Et HFHI 1 CF ₂ CF ₃ Et H Cl Cl H 2
CF ₂ CF ₃ Et HFHI 2 CF ₂ CF ₃ Et H Br Br H 0
CF ₂ CF ₃ Et H Cl HF 0 CF ₂ CF ₃ Et H Br Br H 1
CF ₂ CF ₃ Et H Cl HF 1 CF ₂ CF ₃ Et H Br Br H 2
CF ₂ CF ₃ Et H Cl HF 2 CF ₂ CF ₃ Et HIIH 0
CF ₂ CF ₃ Et H Cl H Br 0 CF ₂ CF ₃ Et HIIH 1
CF ₂ CF ₃ Et H Cl H Br 1 CF ₂ CF ₃ Et HIIH 2
CF ₂ CF ₃ Et H Cl H Br 2 CF ₂ CF ₃ Et HF Cl H 0
――――――――――――――――――― ――――――――――――――――――――
Continuation of [Table 2] Continuation of [Table 2]
――――――――――――――――――― ――――――――――――――――――――
W1 R ¹ Y1 Y2 Y3 Y4 n W1 R ¹ Y1 Y2 Y3 Y4 n
――――――――――――――――――― ――――――――――――――――――――
CF ₂ CF ₃ Et HF Cl H 1 SCF ₃ Et HHHH 0
CF ₂ CF ₃ Et HF Cl H 2 SCF ₃ Et HHHH 1
CF ₂ CF ₃ Et HF Br H 0 SCF ₃ Et HHHH 2
CF ₂ CF ₃ Et HF Br H 1 SCF ₃ Et FHHH 0
CF ₂ CF ₃ Et HF Br H 2 SCF ₃ Et FHHH 1
CF ₂ CF ₃ Et HFIH 0 SCF ₃ Et FHHH 2
CF ₂ CF ₃ Et HFIH 1 SCF ₃ Et Cl HHH 0
CF ₂ CF ₃ Et HFIH 2 SCF ₃ Et Cl HHH 1
CF ₂ CF ₃ Et H Cl FH 0 SCF ₃ Et Cl HHH 2
CF ₂ CF ₃ Et H Cl FH 1 SCF ₃ Et Br HHH 0
CF ₂ CF ₃ Et H Cl FH 2 SCF ₃ Et Br HHH 1
CF ₂ CF ₃ Et H Cl Br H 0 SCF ₃ Et Br HHH 2
CF ₂ CF ₃ Et H Cl Br H 1 SCF ₃ Et IHHH 0
CF ₂ CF ₃ Et H Cl Br H 2 SCF ₃ Et IHHH 1
CF ₂ CF ₃ Et H Cl IH 0 SCF ₃ Et IHHH 2
CF ₂ CF ₃ Et H Cl IH 1 SCF ₃ Et Me HHH 0
CF ₂ CF ₃ Et H Cl IH 2 SCF ₃ Et Me HHH 1
CF ₂ CF ₃ Et H Br FH 0 SCF ₃ Et Me HHH 2
CF ₂ CF ₃ Et H Br FH 1 SCF ₃ Et CF ₃ HHH 0
CF ₂ CF ₃ Et H Br FH 2 SCF ₃ Et CF ₃ HHH 1
CF ₂ CF ₃ Et H Br Cl H 0 SCF ₃ Et CF ₃ HHH 2
CF ₂ CF ₃ Et H Br Cl H 1 SCF ₃ Et HFHH 0
CF ₂ CF ₃ Et H Br Cl H 2 SCF ₃ Et HFHH 1
――――――――――――――――――― ――――――――――――――――――――
Continuation of [Table 2] Continuation of [Table 2]
――――――――――――――――――― ――――――――――――――――――――
W1 R ¹ Y1 Y2 Y3 Y4 n W1 R ¹ Y1 Y2 Y3 Y4 n
――――――――――――――――――― ――――――――――――――――――――
CF ₂ CF ₃ Et H Br IH 0 SCF ₃ Et HFHH 2
CF ₂ CF ₃ Et H Br IH 1 SCF ₃ Et H Cl HH 0
CF ₂ CF ₃ Et H Br IH 2 SCF ₃ Et H Cl HH 1
CF ₂ CF ₃ Et HIFH 0 SCF ₃ Et H Cl HH 2
CF ₂ CF ₃ Et HIFH 1 SCF ₃ Et H Br HH 0
CF ₂ CF ₃ Et HIFH 2 SCF ₃ Et H Br HH 1
CF ₂ CF ₃ Et HI Cl H 0 SCF ₃ Et H Br HH 2
CF ₂ CF ₃ Et HI Cl H 1 SCF ₃ Et HIHH 0
CF ₂ CF ₃ Et HI Cl H 2 SCF ₃ Et HIHH 1
CF ₂ CF ₃ Et HI Br H 0 SCF ₃ Et HIHH 2
CF ₂ CF ₃ Et HI Br H 1 SCF ₃ Et H Me HH 0
CF ₂ CF ₃ Et HI Br H 2 SCF ₃ Et H Me HH 1
CF ₂ CF ₃ Et HF CN H 0 SCF ₃ Et H Me HH 2
CF ₂ CF ₃ Et HF CN H 1 SCF ₃ Et H CF ₃ HH 0
CF ₂ CF ₃ Et HF CN H 2 SCF ₃ Et H CF ₃ HH 1
CF ₂ CF ₃ Et H Cl CN H 0 SCF ₃ Et H CF ₃ HH 2
CF ₂ CF ₃ Et H Cl CN H 1 SCF ₃ Et H CF ₂ CF ₃ HH 0
CF ₂ CF ₃ Et H Cl CN H 2 SCF ₃ Et H CF ₂ CF ₃ HH 1
CF ₂ CF ₃ Et H Br CN H 0 SCF ₃ Et H CF ₂ CF ₃ HH 2
CF ₂ CF ₃ Et H Br CN H 1 SCF ₃ Et H CF(CF ₃ ) ₂ HH 0
CF ₂ CF ₃ Et H Br CN H 2 SCF ₃ Et H CF(CF ₃ ) ₂ HH 1
CF ₂ CF ₃ Et HI CN H 0 SCF ₃ Et H CF(CF ₃ ) ₂ HH 2
CF ₂ CF ₃ Et HI CN H 1 SCF ₃ Et H SMe HH 0
CF ₂ CF ₃ Et HI CN H 2 SCF ₃ Et H SMe HH 1
CF ₂ CF ₃ Et H CF ₃ FH 0 SCF ₃ Et H SMe HH 2
CF ₂ CF ₃ Et H CF ₃ FH 1 SCF ₃ Et H SOMe HH 0
CF ₂ CF ₃ Et H CF ₃ FH 2 SCF ₃ Et H SOMe HH 1
CF ₂ CF ₃ Et H CF ₃ Cl H 0 SCF ₃ Et H SOMe HH 2
CF ₂ CF ₃ Et H CF ₃ Cl H 1 SCF ₃ Et H SO ₂ Me HH 0
CF ₂ CF ₃ Et H CF ₃ Cl H 2 SCF ₃ Et H SO ₂ Me HH 1
CF ₂ CF ₃ Et H CF ₃ Br H 0 SCF ₃ Et H SO ₂ Me HH 2
CF ₂ CF ₃ Et H CF ₃ Br H 1 SCF ₃ Et H OMe HH 0
CF ₂ CF ₃ Et H CF ₃ Br H 2 SCF ₃ Et H OMe HH 1
CF ₂ CF ₃ Et H CF ₃ IH 0 SCF ₃ Et H OMe HH 2
CF ₂ CF ₃ Et H CF ₃ IH 1 SCF ₃ Et H OCF ₃ HH 0
CF ₂ CF ₃ Et H CF ₃ IH 2 SCF ₃ Et H OCF ₃ HH 1
CF ₂ CF ₃ Et H CF ₃ CN H 0 SCF ₃ Et H OCF ₃ HH 2
CF ₂ CF ₃ Et H CF ₃ CN H 1 SCF ₃ Et H NO ₂ HH 0
CF ₂ CF ₃ Et H CF ₃ CN H 2 ――――――――――――――――――――――
―――――――――――――――――――
Continuation of [Table 2] Continuation of [Table 2]
――――――――――――――――――― ――――――――――――――――――――
W1 R ¹ Y1 Y2 Y3 Y4 n W1 R ¹ Y1 Y2 Y3 Y4 n
――――――――――――――――――― ――――――――――――――――――――
SCF ₃ Et H NO ₂ HH 1 SCF ₃ Et HHHI 2
SCF ₃ Et H NO ₂ HH 2 SCF ₃ Et HHH Me 0
SCF ₃ Et H CN HH 0 SCF ₃ Et HHH Me 1
SCF ₃ Et H CN HH 1 SCF ₃ Et HHH Me 2
SCF ₃ Et H CN HH 2 SCF ₃ Et HHH CF ₃ 0
SCF ₃ Et HHFH 0 SCF ₃ Et HHH CF ₃ 1
SCF ₃ Et HHFH 1 SCF ₃ Et HHH CF ₃ 2
SCF ₃ Et HHFH 2 SCF ₃ Et HHH CF ₂ CF ₃ 0
SCF ₃ Et HH Cl H 0 SCF ₃ Et HHH CF ₂ CF ₃ 1
SCF ₃ Et HH Cl H 1 SCF ₃ Et HHH CF ₂ CF ₃ 2
SCF ₃ Et HH Cl H 2 SCF ₃ Et HHH CF(CF ₃ ) ₂ 0
SCF ₃ Et HH Br H 0 SCF ₃ Et HHH CF(CF ₃ ) ₂ 1
SCF ₃ Et HH Br H 1 SCF ₃ Et HHH CF(CF ₃ ) ₂ 2
SCF ₃ Et HH Br H 2 SCF ₃ Et HHH SMe 0
SCF ₃ Et HHIH 0 SCF ₃ Et HHH SMe 1
SCF ₃ Et HHIH 1 SCF ₃ Et HHH SMe 2
SCF ₃ Et HHIH 2 SCF ₃ Et HHH SOMe 0
SCF ₃ Et HH Me H 0 SCF ₃ Et HHH SOMe 1
SCF ₃ Et HH Me H 1 SCF ₃ Et HHH SOMe 2
SCF ₃ Et HH Me H 2 SCF ₃ Et HHH SO ₂ Me 0
SCF ₃ Et HH CF ₃ H 0 SCF ₃ Et HHH SO ₂ Me 1
SCF ₃ Et HH CF ₃ H 1 SCF ₃ Et HHH SO ₂ Me 2
SCF ₃ Et HH CF ₃ H 2 SCF ₃ Et HHH OMe 0
SCF ₃ Et HH CF ₂ CF ₃ H 0 SCF ₃ Et HHH OMe 1
SCF ₃ Et HH CF ₂ CF ₃ H 1 SCF ₃ Et HHH OMe 2
SCF ₃ Et HH CF ₂ CF ₃ H 2 SCF ₃ Et HHH OCF ₃ 0
SCF ₃ Et HH CF(CF ₃ ) ₂ H 0 SCF ₃ Et HHH OCF ₃ 1
SCF ₃ Et HH CF(CF ₃ ) ₂ H 1 SCF ₃ Et HHH OCF ₃ 2
SCF ₃ Et HH CF(CF ₃ ) ₂ H 2 SCF ₃ Et HHH NO ₂ 0
SCF ₃ Et HH SMe H 0 SCF ₃ Et HHH NO ₂ 1
SCF ₃ Et HH SMe H 1 SCF ₃ Et HHH NO ₂ 2
SCF ₃ Et HH SMe H 2 SCF ₃ Et HHH CN 0
SCF ₃ Et HH SOMe H 0 SCF ₃ Et HHH CN 1
SCF ₃ Et HH SOMe H 1 SCF ₃ Et HHH CN 2
SCF ₃ Et HH SOMe H 2 SCF ₃ Et HFHF 0
――――――――――――――――――― ――――――――――――――――――――
Continuation of [Table 2] Continuation of [Table 2]
――――――――――――――――――― ――――――――――――――――――――
W1 R ¹ Y1 Y2 Y3 Y4 n W1 R ¹ Y1 Y2 Y3 Y4 n
――――――――――――――――――― ――――――――――――――――――――
SCF ₃ Et HH SO ₂ Me H 0 SCF ₃ Et HFHF 1
SCF ₃ Et HH SO ₂ Me H 1 SCF ₃ Et HFHF 2
SCF ₃ Et HH SO ₂ Me H 2 SCF ₃ Et H Cl H Cl 0
SCF ₃ Et HH OMe H 0 SCF ₃ Et H Cl H Cl 1
SCF ₃ Et HH OMe H 1 SCF ₃ Et H Cl H Cl 2
SCF ₃ Et HH OMe H 2 SCF ₃ Et H Br H Br 0
SCF ₃ Et HH OCF ₃ H 0 SCF ₃ Et H Br H Br 1
SCF ₃ Et HH OCF ₃ H 1 SCF ₃ Et H Br H Br 2
SCF ₃ Et HH OCF ₃ H 2 SCF ₃ Et HIHI 0
SCF ₃ Et HH NO ₂ H 0 SCF ₃ Et HIHI 1
SCF ₃ Et HH NO ₂ H 1 SCF ₃ Et HIHI 2
SCF ₃ Et HH NO ₂ H 2 SCF ₃ Et HFH Cl 0
SCF ₃ Et HH CN H 0 SCF ₃ Et HFH Cl 1
SCF ₃ Et HH CN H 1 SCF ₃ Et HFH Cl 2
SCF ₃ Et HH CN H 2 SCF ₃ Et HFH Br 0
SCF ₃ Et HHHF 0 SCF ₃ Et HFH Br 1
SCF ₃ Et HHHF 1 SCF ₃ Et HFH Br 2
SCF ₃ Et HHHF 2 SCF ₃ Et HFHI 0
SCF ₃ Et HHH Cl 0 SCF ₃ Et HFHI 1
SCF ₃ Et HHH Cl 1 SCF ₃ Et HFHI 2
SCF ₃ Et HHH Cl 2 SCF ₃ Et H Cl HF 0
SCF ₃ Et HHH Br 0 SCF ₃ Et H Cl HF 1
SCF ₃ Et HHH Br 1 SCF ₃ Et H Cl HF 2
SCF ₃ Et HHH Br 2 SCF ₃ Et H Cl H Br 0
SCF ₃ Et HHHI 0 SCF ₃ Et H Cl H Br 1
SCF ₃ Et HHHI 1 SCF ₃ Et H Cl H Br 2
――――――――――――――――――― ――――――――――――――――――――
Continuation of [Table 2] Continuation of [Table 2]
――――――――――――――――――― ――――――――――――――――――――
W1 R ¹ Y1 Y2 Y3 Y4 n W1 R ¹ Y1 Y2 Y3 Y4 n
――――――――――――――――――― ――――――――――――――――――――
SCF ₃ Et H Cl HI 0 SCF ₃ Et HF Cl H 1
SCF ₃ Et H Cl HI 1 SCF ₃ Et HF Cl H 2
SCF ₃ Et H Cl HI 2 SCF ₃ Et HF Br H 0
SCF ₃ Et H Br HF 0 SCF ₃ Et HF Br H 1
SCF ₃ Et H Br HF 1 SCF ₃ Et HF Br H 2
SCF ₃ Et H Br HF 2 SCF ₃ Et HFIH 0
SCF ₃ Et H Br H Cl 0 SCF ₃ Et HFIH 1
SCF ₃ Et H Br H Cl 1 SCF ₃ Et HFIH 2
SCF ₃ Et H Br H Cl 2 SCF ₃ Et H Cl FH 0
SCF ₃ Et H Br HI 0 SCF ₃ Et H Cl FH 1
SCF ₃ Et H Br HI 1 SCF ₃ Et H Cl FH 2
SCF ₃ Et H Br HI 2 SCF ₃ Et H Cl Br H 0
SCF ₃ Et HIHF 0 SCF ₃ Et H Cl Br H 1
SCF ₃ Et HIHF 1 SCF ₃ Et H Cl Br H 2
SCF ₃ Et HIHF 2 SCF ₃ Et H Cl IH 0
SCF ₃ Et HIH Cl 0 SCF ₃ Et H Cl IH 1
SCF ₃ Et HIH Cl 1 SCF ₃ Et H Cl IH 2
SCF ₃ Et HIH Cl 2 SCF ₃ Et H Br FH 0
SCF ₃ Et HIH Br 0 SCF ₃ Et H Br FH 1
SCF ₃ Et HIH Br 1 SCF ₃ Et H Br FH 2
SCF ₃ Et HIH Br 2 SCF ₃ Et H Br Cl H 0
SCF ₃ Et HFH CN 0 SCF ₃ Et H Br Cl H 1
SCF ₃ Et HFH CN 1 SCF ₃ Et H Br Cl H 2
SCF ₃ Et HFH CN 2 SCF ₃ Et H Br IH 0
SCF ₃ Et H Cl H CN 0 SCF ₃ Et H Br IH 1
SCF ₃ Et H Cl H CN 1 SCF ₃ Et H Br IH 2
SCF ₃ Et H Cl H CN 2 SCF ₃ Et HIFH 0
――――――――――――――――――― ――――――――――――――――――――
Continuation of [Table 2] Continuation of [Table 2]
――――――――――――――――――― ――――――――――――――――――――
W1 R ¹ Y1 Y2 Y3 Y4 n W1 R ¹ Y1 Y2 Y3 Y4 n
――――――――――――――――――― ――――――――――――――――――――
SCF ₃ Et H Br H CN 0 SCF ₃ Et HIFH 1
SCF ₃ Et H Br H CN 1 SCF ₃ Et HIFH 2
SCF ₃ Et H Br H CN 2 SCF ₃ Et HI Cl H 0
SCF ₃ Et HIH CN 0 SCF ₃ Et HI Cl H 1
SCF ₃ Et HIH CN 1 SCF ₃ Et HI Cl H 2
SCF ₃ Et HIH CN 2 SCF ₃ Et HI Br H 0
SCF ₃ Et H CF ₃ HF 0 SCF ₃ Et HI Br H 1
SCF ₃ Et H CF ₃ HF 1 SCF ₃ Et HI Br H 2
SCF ₃ Et H CF ₃ HF 2 SCF ₃ Et HF CN H 0
SCF ₃ Et H CF ₃ H Cl 0 SCF ₃ Et HF CN H 1
SCF ₃ Et H CF ₃ H Cl 1 SCF ₃ Et HF CN H 2
SCF ₃ Et H CF ₃ H Cl 2 SCF ₃ Et H Cl CN H 0
SCF ₃ Et H CF ₃ H Br 0 SCF ₃ Et H Cl CN H 1
SCF ₃ Et H CF ₃ H Br 1 SCF ₃ Et H Cl CN H 2
SCF ₃ Et H CF ₃ H Br 2 SCF ₃ Et H Br CN H 0
SCF ₃ Et H CF ₃ HI 0 SCF ₃ Et H Br CN H 1
SCF ₃ Et H CF ₃ HI 1 SCF ₃ Et H Br CN H 2
SCF ₃ Et H CF ₃ HI 2 SCF ₃ Et HI CN H 0
SCF ₃ Et H CF ₃ H CN 0 SCF ₃ Et HI CN H 1
SCF ₃ Et H CF ₃ H CN 1 SCF ₃ Et HI CN H 2
SCF ₃ Et H CF ₃ H CN 2 SCF ₃ Et H CF ₃ FH 0
SCF ₃ Et HFFH 0 SCF ₃ Et H CF ₃ FH 1
SCF ₃ Et HFFH 1 SCF ₃ Et H CF ₃ FH 2
SCF ₃ Et HFFH 2 SCF ₃ Et H CF ₃ Cl H 0
SCF ₃ Et H Cl Cl H 0 SCF ₃ Et H CF ₃ Cl H 1
SCF ₃ Et H Cl Cl H 1 SCF ₃ Et H CF ₃ Cl H 2
SCF ₃ Et H Cl Cl H 2 SCF ₃ Et H CF ₃ Br H 0
SCF ₃ Et H Br Br H 0 SCF ₃ Et H CF ₃ Br H 1
SCF ₃ Et H Br Br H 1 SCF ₃ Et H CF ₃ Br H 2
SCF ₃ Et H Br Br H 2 SCF ₃ Et H CF ₃ IH 0
SCF ₃ Et HIIH 0 SCF ₃ Et H CF ₃ IH 1
SCF ₃ Et HIIH 1 SCF ₃ Et H CF ₃ IH 2
SCF ₃ Et HIIH 2 SCF ₃ Et H CF ₃ CN H 0
SCF ₃ Et HF Cl H 0 SCF ₃ Et H CF ₃ CN H 1
――――――――――――――――――― SCF ₃ Et H CF ₃ CN H 2
――――――――――――――――――――

Continuation of [Table 2] Continuation of [Table 2]
――――――――――――――――――― ――――――――――――――――――――
W1 R ¹ Y1 Y2 Y3 Y4 n W1 R ¹ Y1 Y2 Y3 Y4 n
――――――――――――――――――― ――――――――――――――――――――
SOCF ₃ Et HHHH 0 SOCF ₃ Et H NO ₂ HH 1
SOCF ₃ Et HHHH 1 SOCF ₃ Et H NO ₂ HH 2
SOCF ₃ Et HHHH 2 SOCF ₃ Et H CN HH 0
SOCF ₃ Et FHHH 0 SOCF ₃ Et H CN HH 1
SOCF ₃ Et FHHH 1 SOCF ₃ Et H CN HH 2
SOCF ₃ Et FHHH 2 SOCF ₃ Et HHFH 0
SOCF ₃ Et Cl HHH 0 SOCF ₃ Et HHFH 1
SOCF ₃ Et Cl HHH 1 SOCF ₃ Et HHFH 2
SOCF ₃ Et Cl HHH 2 SOCF ₃ Et HH Cl H 0
SOCF ₃ Et Br HHH 0 SOCF ₃ Et HH Cl H 1
SOCF ₃ Et Br HHH 1 SOCF ₃ Et HH Cl H 2
SOCF ₃ Et Br HHH 2 SOCF ₃ Et HH Br H 0
SOCF ₃ Et IHHH 0 SOCF ₃ Et HH Br H 1
SOCF ₃ Et IHHH 1 SOCF ₃ Et HH Br H 2
SOCF ₃ Et IHHH 2 SOCF ₃ Et HHIH 0
SOCF ₃ Et Me HHH 0 SOCF ₃ Et HHIH 1
SOCF ₃ Et Me HHH 1 SOCF ₃ Et HHIH 2
SOCF ₃ Et Me HHH 2 SOCF ₃ Et HH Me H 0
SOCF ₃ Et CF ₃ HHH 0 SOCF ₃ Et HH Me H 1
SOCF ₃ Et CF ₃ HHH 1 SOCF ₃ Et HH Me H 2
SOCF ₃ Et CF ₃ HHH 2 SOCF ₃ Et HH CF ₃ H 0
SOCF ₃ Et HFHH 0 SOCF ₃ Et HH CF ₃ H 1
SOCF ₃ Et HFHH 1 SOCF ₃ Et HH CF ₃ H 2
SOCF ₃ Et HFHH 2 SOCF ₃ Et HH CF ₂ CF ₃ H 0
SOCF ₃ Et H Cl HH 0 SOCF ₃ Et HH CF ₂ CF ₃ H 1
SOCF ₃ Et H Cl HH 1 SOCF ₃ Et HH CF ₂ CF ₃ H 2
SOCF ₃ Et H Cl HH 2 SOCF ₃ Et HH CF(CF ₃ ) ₂ H 0
SOCF ₃ Et H Br HH 0 SOCF ₃ Et HH CF(CF ₃ ) ₂ H 1
SOCF ₃ Et H Br HH 1 SOCF ₃ Et HH CF(CF ₃ ) ₂ H 2
SOCF ₃ Et H Br HH 2 SOCF ₃ Et HH SMe H 0
――――――――――――――――――― ――――――――――――――――――――
Continuation of [Table 2] Continuation of [Table 2]
――――――――――――――――――― ――――――――――――――――――――
W1 R ¹ Y1 Y2 Y3 Y4 n W1 R ¹ Y1 Y2 Y3 Y4 n
――――――――――――――――――― ――――――――――――――――――――
SOCF ₃ Et HIHH 0 SOCF ₃ Et HH SMe H 1
SOCF ₃ Et HIHH 1 SOCF ₃ Et HH SMe H 2
SOCF ₃ Et HIHH 2 SOCF ₃ Et HH SOMe H 0
SOCF ₃ Et H Me HH 0 SOCF ₃ Et HH SOMe H 1
SOCF ₃ Et H Me HH 1 SOCF ₃ Et HH SOMe H 2
SOCF ₃ Et H Me HH 2 SOCF ₃ Et HH SO ₂ Me H 0
SOCF ₃ Et H CF ₃ HH 0 SOCF ₃ Et HH SO ₂ Me H 1
SOCF ₃ Et H CF ₃ HH 1 SOCF ₃ Et HH SO ₂ Me H 2
SOCF ₃ Et H CF ₃ HH 2 SOCF ₃ Et HH OMe H 0
SOCF ₃ Et H CF ₂ CF ₃ HH 0 SOCF ₃ Et HH OMe H 1
SOCF ₃ Et H CF ₂ CF ₃ HH 1 SOCF ₃ Et HH OMe H 2
SOCF ₃ Et H CF ₂ CF ₃ HH 2 SOCF ₃ Et HH OCF ₃ H 0
SOCF ₃ Et H CF(CF ₃ ) ₂ HH 0 SOCF ₃ Et HH OCF ₃ H 1
SOCF ₃ Et H CF(CF ₃ ) ₂ HH 1 SOCF ₃ Et HH OCF ₃ H 2
SOCF ₃ Et H CF(CF ₃ ) ₂ HH 2 SOCF ₃ Et HH NO ₂ H 0
SOCF ₃ Et H SMe HH 0 SOCF ₃ Et HH NO ₂ H 1
SOCF ₃ Et H SMe HH 1 SOCF ₃ Et HH NO ₂ H 2
SOCF ₃ Et H SMe HH 2 SOCF ₃ Et HH CN H 0
SOCF ₃ Et H SOMe HH 0 SOCF ₃ Et HH CN H 1
SOCF ₃ Et H SOMe HH 1 SOCF ₃ Et HH CN H 2
SOCF ₃ Et H SOMe HH 2 SOCF ₃ Et HHHF 0
SOCF ₃ Et H SO ₂ Me HH 0 SOCF ₃ Et HHHF 1
SOCF ₃ Et H SO ₂ Me HH 1 SOCF ₃ Et HHHF 2
SOCF ₃ Et H SO ₂ Me HH 2 SOCF ₃ Et HHH Cl 0
SOCF ₃ Et H OMe HH 0 SOCF ₃ Et HHH Cl 1
SOCF ₃ Et H OMe HH 1 SOCF ₃ Et HHH Cl 2
SOCF ₃ Et H OMe HH 2 SOCF ₃ Et HHH Br 0
SOCF ₃ Et H OCF ₃ HH 0 SOCF ₃ Et HHH Br 1
SOCF ₃ Et H OCF ₃ HH 1 SOCF ₃ Et HHH Br 2
SOCF ₃ Et H OCF ₃ HH 2 SOCF ₃ Et HHHI 0
SOCF ₃ Et H NO ₂ HH 0 SOCF ₃ Et HHHI 1
――――――――――――――――――― ――――――――――――――――――――
Continuation of [Table 2] Continuation of [Table 2]
――――――――――――――――――― ――――――――――――――――――――
W1 R ¹ Y1 Y2 Y3 Y4 n W1 R ¹ Y1 Y2 Y3 Y4 n
――――――――――――――――――― ――――――――――――――――――――
SOCF ₃ Et HHHI 2 SOCF ₃ Et H Cl HI 0
SOCF ₃ Et HHH Me 0 SOCF ₃ Et H Cl HI 1
SOCF ₃ Et HHH Me 1 SOCF ₃ Et H Cl HI 2
SOCF ₃ Et HHH Me 2 SOCF ₃ Et H Br HF 0
SOCF ₃ Et HHH CF ₃ 0 SOCF ₃ Et H Br HF 1
SOCF ₃ Et HHH CF ₃ 1 SOCF ₃ Et H Br HF 2
SOCF ₃ Et HHH CF ₃ 2 SOCF ₃ Et H Br H Cl 0
SOCF ₃ Et HHH CF ₂ CF ₃ 0 SOCF ₃ Et H Br H Cl 1
SOCF ₃ Et HHH CF ₂ CF ₃ 1 SOCF ₃ Et H Br H Cl 2
SOCF ₃ Et HHH CF ₂ CF ₃ 2 SOCF ₃ Et H Br HI 0
SOCF ₃ Et HHH CF(CF ₃ ) ₂ 0 SOCF ₃ Et H Br HI 1
SOCF ₃ Et HHH CF(CF ₃ ) ₂ 1 SOCF ₃ Et H Br HI 2
SOCF ₃ Et HHH CF(CF ₃ ) ₂ 2 SOCF ₃ Et HIHF 0
SOCF ₃ Et HHH SMe 0 SOCF ₃ Et HIHF 1
SOCF ₃ Et HHH SMe 1 SOCF ₃ Et HIHF 2
SOCF ₃ Et HHH SMe 2 SOCF ₃ Et HIH Cl 0
SOCF ₃ Et HHH SOMe 0 SOCF ₃ Et HIH Cl 1
SOCF ₃ Et HHH SOMe 1 SOCF ₃ Et HIH Cl 2
SOCF ₃ Et HHH SOMe 2 SOCF ₃ Et HIH Br 0
SOCF ₃ Et HHH SO ₂ Me 0 SOCF ₃ Et HIH Br 1
SOCF ₃ Et HHH SO ₂ Me 1 SOCF ₃ Et HIH Br 2
SOCF ₃ Et HHH SO ₂ Me 2 SOCF ₃ Et HFH CN 0
SOCF ₃ Et HHH OMe 0 SOCF ₃ Et HFH CN 1
SOCF ₃ Et HHH OMe 1 SOCF ₃ Et HFH CN 2
SOCF ₃ Et HHH OMe 2 SOCF ₃ Et H Cl H CN 0
SOCF ₃ Et HHH OCF ₃ 0 SOCF ₃ Et H Cl H CN 1
SOCF ₃ Et HHH OCF ₃ 1 SOCF ₃ Et H Cl H CN 2
SOCF ₃ Et HHH OCF ₃ 2 SOCF ₃ Et H Br H CN 0
――――――――――――――――――― ――――――――――――――――――――
Continuation of [Table 2] Continuation of [Table 2]
――――――――――――――――――― ――――――――――――――――――――
W1 R ¹ Y1 Y2 Y3 Y4 n W1 R ¹ Y1 Y2 Y3 Y4 n
――――――――――――――――――― ――――――――――――――――――――
SOCF ₃ Et HHH NO ₂ 0 SOCF ₃ Et H Br H CN 1
SOCF ₃ Et HHH NO ₂ 1 SOCF ₃ Et H Br H CN 2
SOCF ₃ Et HHH NO ₂ 2 SOCF ₃ Et HIH CN 0
SOCF ₃ Et HHH CN 0 SOCF ₃ Et HIH CN 1
SOCF ₃ Et HHH CN 1 SOCF ₃ Et HIH CN 2
SOCF ₃ Et HHH CN 2 SOCF ₃ Et H CF ₃ HF 0
SOCF ₃ Et HFHF 0 SOCF ₃ Et H CF ₃ HF 1
SOCF ₃ Et HFHF 1 SOCF ₃ Et H CF ₃ HF 2
SOCF ₃ Et HFHF 2 SOCF ₃ Et H CF ₃ H Cl 0
SOCF ₃ Et H Cl H Cl 0 SOCF ₃ Et H CF ₃ H Cl 1
SOCF ₃ Et H Cl H Cl 1 SOCF ₃ Et H CF ₃ H Cl 2
SOCF ₃ Et H Cl H Cl 2 SOCF ₃ Et H CF ₃ H Br 0
SOCF ₃ Et H Br H Br 0 SOCF ₃ Et H CF ₃ H Br 1
SOCF ₃ Et H Br H Br 1 SOCF ₃ Et H CF ₃ H Br 2
SOCF ₃ Et H Br H Br 2 SOCF ₃ Et H CF ₃ HI 0
SOCF ₃ Et HIHI 0 SOCF ₃ Et H CF ₃ HI 1
SOCF ₃ Et HIHI 1 SOCF ₃ Et H CF ₃ HI 2
SOCF ₃ Et HIHI 2 SOCF ₃ Et H CF ₃ H CN 0
SOCF ₃ Et HFH Cl 0 SOCF ₃ Et H CF ₃ H CN 1
SOCF ₃ Et HFH Cl 1 SOCF ₃ Et H CF ₃ H CN 2
SOCF ₃ Et HFH Cl 2 SOCF ₃ Et HFFH 0
SOCF ₃ Et HFH Br 0 SOCF ₃ Et HFFH 1
SOCF ₃ Et HFH Br 1 SOCF ₃ Et HFFH 2
SOCF ₃ Et HFH Br 2 SOCF ₃ Et H Cl Cl H 0
SOCF ₃ Et HFHI 0 SOCF ₃ Et H Cl Cl H 1
SOCF ₃ Et HFHI 1 SOCF ₃ Et H Cl Cl H 2
SOCF ₃ Et HFHI 2 SOCF ₃ Et H Br Br H 0
SOCF ₃ Et H Cl HF 0 SOCF ₃ Et H Br Br H 1
SOCF ₃ Et H Cl HF 1 SOCF ₃ Et H Br Br H 2
SOCF ₃ Et H Cl HF 2 SOCF ₃ Et HIIH 0
SOCF ₃ Et H Cl H Br 0 SOCF ₃ Et HIIH 1
SOCF ₃ Et H Cl H Br 1 SOCF ₃ Et HIIH 2
SOCF ₃ Et H Cl H Br 2 SOCF ₃ Et HF Cl H 0
――――――――――――――――――― ――――――――――――――――――――
Continuation of [Table 2] Continuation of [Table 2]
――――――――――――――――――― ――――――――――――――――――――
W1 R ¹ Y1 Y2 Y3 Y4 n W1 R ¹ Y1 Y2 Y3 Y4 n
――――――――――――――――――― ――――――――――――――――――――
SOCF ₃ Et HF Cl H 1 SO ₂ CF ₃ Et HHHH 0
SOCF ₃ Et HF Cl H 2 SO ₂ CF ₃ Et HHHH 1
SOCF ₃ Et HF Br H 0 SO ₂ CF ₃ Et HHHH 2
SOCF ₃ Et HF Br H 1 SO ₂ CF ₃ Et FHHH 0
SOCF ₃ Et HF Br H 2 SO ₂ CF ₃ Et FHHH 1
SOCF ₃ Et HFIH 0 SO ₂ CF ₃ Et FHHH 2
SOCF ₃ Et HFIH 1 SO ₂ CF ₃ Et Cl HHH 0
SOCF ₃ Et HFIH 2 SO ₂ CF ₃ Et Cl HHH 1
SOCF ₃ Et H Cl FH 0 SO ₂ CF ₃ Et Cl HHH 2
SOCF ₃ Et H Cl FH 1 SO ₂ CF ₃ Et Br HHH 0
SOCF ₃ Et H Cl FH 2 SO ₂ CF ₃ Et Br HHH 1
SOCF ₃ Et H Cl Br H 0 SO ₂ CF ₃ Et Br HHH 2
SOCF ₃ Et H Cl Br H 1 SO ₂ CF ₃ Et IHHH 0
SOCF ₃ Et H Cl Br H 2 SO ₂ CF ₃ Et IHHH 1
SOCF ₃ Et H Cl IH 0 SO ₂ CF ₃ Et IHHH 2
SOCF ₃ Et H Cl IH 1 SO ₂ CF ₃ Et Me HHH 0
SOCF ₃ Et H Cl IH 2 SO ₂ CF ₃ Et Me HHH 1
SOCF ₃ Et H Br FH 0 SO ₂ CF ₃ Et Me HHH 2
SOCF ₃ Et H Br FH 1 SO ₂ CF ₃ Et CF ₃ HHH 0
SOCF ₃ Et H Br FH 2 SO ₂ CF ₃ Et CF ₃ HHH 1
SOCF ₃ Et H Br Cl H 0 SO ₂ CF ₃ Et CF ₃ HHH 2
SOCF ₃ Et H Br Cl H 1 SO ₂ CF ₃ Et HFHH 0
SOCF ₃ Et H Br Cl H 2 SO ₂ CF ₃ Et HFHH 1
――――――――――――――――――― ――――――――――――――――――――
Continuation of [Table 2] Continuation of [Table 2]
――――――――――――――――――― ――――――――――――――――――――
W1 R ¹ Y1 Y2 Y3 Y4 n W1 R ¹ Y1 Y2 Y3 Y4 n
――――――――――――――――――― ――――――――――――――――――――
SOCF ₃ Et H Br IH 0 SO ₂ CF ₃ Et HFHH 2
SOCF ₃ Et H Br IH 1 SO ₂ CF ₃ Et H Cl HH 0
SOCF ₃ Et H Br IH 2 SO ₂ CF ₃ Et H Cl HH 1
SOCF ₃ Et HIFH 0 SO ₂ CF ₃ Et H Cl HH 2
SOCF ₃ Et HIFH 1 SO ₂ CF ₃ Et H Br HH 0
SOCF ₃ Et HIFH 2 SO ₂ CF ₃ Et H Br HH 1
SOCF ₃ Et HI Cl H 0 SO ₂ CF ₃ Et H Br HH 2
SOCF ₃ Et HI Cl H 1 SO ₂ CF ₃ Et HIHH 0
SOCF ₃ Et HI Cl H 2 SO ₂ CF ₃ Et HIHH 1
SOCF ₃ Et HI Br H 0 SO ₂ CF ₃ Et HIHH 2
SOCF ₃ Et HI Br H 1 SO ₂ CF ₃ Et H Me HH 0
SOCF ₃ Et HI Br H 2 SO ₂ CF ₃ Et H Me HH 1
SOCF ₃ Et HF CN H 0 SO ₂ CF ₃ Et H Me HH 2
SOCF ₃ Et HF CN H 1 SO ₂ CF ₃ Et H CF ₃ HH 0
SOCF ₃ Et HF CN H 2 SO ₂ CF ₃ Et H CF ₃ HH 1
SOCF ₃ Et H Cl CN H 0 SO ₂ CF ₃ Et H CF ₃ HH 2
SOCF ₃ Et H Cl CN H 1 SO ₂ CF ₃ Et H CF ₂ CF ₃ HH 0
SOCF ₃ Et H Cl CN H 2 SO ₂ CF ₃ Et H CF ₂ CF ₃ HH 1
SOCF ₃ Et H Br CN H 0 SO ₂ CF ₃ Et H CF ₂ CF ₃ HH 2
SOCF ₃ Et H Br CN H 1 SO ₂ CF ₃ Et H CF(CF ₃ ) ₂ HH 0
SOCF ₃ Et H Br CN H 2 SO ₂ CF ₃ Et H CF(CF ₃ ) ₂ HH 1
SOCF ₃ Et HI CN H 0 SO ₂ CF ₃ Et H CF(CF ₃ ) ₂ HH 2
SOCF ₃ Et HI CN H 1 SO ₂ CF ₃ Et H SMe HH 0
SOCF ₃ Et HI CN H 2 SO ₂ CF ₃ Et H SMe HH 1
SOCF ₃ Et H CF ₃ FH 0 SO ₂ CF ₃ Et H SMe HH 2
SOCF ₃ Et H CF ₃ FH 1 SO ₂ CF ₃ Et H SOMe HH 0
SOCF ₃ Et H CF ₃ FH 2 SO ₂ CF ₃ Et H SOMe HH 1
SOCF ₃ Et H CF ₃ Cl H 0 SO ₂ CF ₃ Et H SOMe HH 2
SOCF ₃ Et H CF ₃ Cl H 1 SO ₂ CF ₃ Et H SO ₂ Me HH 0
SOCF ₃ Et H CF ₃ Cl H 2 SO ₂ CF ₃ Et H SO ₂ Me HH 1
SOCF ₃ Et H CF ₃ Br H 0 SO ₂ CF ₃ Et H SO ₂ Me HH 2
SOCF ₃ Et H CF ₃ Br H 1 SO ₂ CF ₃ Et H OMe HH 0
SOCF ₃ Et H CF ₃ Br H 2 SO ₂ CF ₃ Et H OMe HH 1
SOCF ₃ Et H CF ₃ IH 0 SO ₂ CF ₃ Et H OMe HH 2
SOCF ₃ Et H CF ₃ IH 1 SO ₂ CF ₃ Et H OCF ₃ HH 0
SOCF ₃ Et H CF ₃ IH 2 SO ₂ CF ₃ Et H OCF ₃ HH 1
SOCF ₃ Et H CF ₃ CN H 0 SO ₂ CF ₃ Et H OCF ₃ HH 2
SOCF ₃ Et H CF ₃ CN H 1 SO ₂ CF ₃ Et H NO ₂ HH 0
SOCF ₃ Et H CF ₃ CN H 2 ――――――――――――――――――――――
―――――――――――――――――――
Continuation of [Table 2] Continuation of [Table 2]
――――――――――――――――――― ――――――――――――――――――――
W1 R ¹ Y1 Y2 Y3 Y4 n W1 R ¹ Y1 Y2 Y3 Y4 n
――――――――――――――――――― ――――――――――――――――――――
SO ₂ CF ₃ Et H NO ₂ HH 1 SO ₂ CF ₃ Et HHHI 2
SO ₂ CF ₃ Et H NO ₂ HH 2 SO ₂ CF ₃ Et HHH Me 0
SO ₂ CF ₃ Et H CN HH 0 SO ₂ CF ₃ Et HHH Me 1
SO ₂ CF ₃ Et H CN HH 1 SO ₂ CF ₃ Et HHH Me 2
SO ₂ CF ₃ Et H CN HH 2 SO ₂ CF ₃ Et HHH CF ₃ 0
SO ₂ CF ₃ Et HHFH 0 SO ₂ CF ₃ Et HHH CF ₃ 1
SO ₂ CF ₃ Et HHFH 1 SO ₂ CF ₃ Et HHH CF ₃ 2
SO ₂ CF ₃ Et HHFH 2 SO ₂ CF ₃ Et HHH CF ₂ CF ₃ 0
SO ₂ CF ₃ Et HH Cl H 0 SO ₂ CF ₃ Et HHH CF ₂ CF ₃ 1
SO ₂ CF ₃ Et HH Cl H 1 SO ₂ CF ₃ Et HHH CF ₂ CF ₃ 2
SO ₂ CF ₃ Et HH Cl H 2 SO ₂ CF ₃ Et HHH CF(CF ₃ ) ₂ 0
SO ₂ CF ₃ Et HH Br H 0 SO ₂ CF ₃ Et HHH CF(CF ₃ ) ₂ 1
SO ₂ CF ₃ Et HH Br H 1 SO ₂ CF ₃ Et HHH CF(CF ₃ ) ₂ 2
SO ₂ CF ₃ Et HH Br H 2 SO ₂ CF ₃ Et HHH SMe 0
SO ₂ CF ₃ Et HHIH 0 SO ₂ CF ₃ Et HHH SMe 1
SO ₂ CF ₃ Et HHIH 1 SO ₂ CF ₃ Et HHH SMe 2
SO ₂ CF ₃ Et HHIH 2 SO ₂ CF ₃ Et HHH SOMe 0
SO ₂ CF ₃ Et HH Me H 0 SO ₂ CF ₃ Et HHH SOMe 1
SO ₂ CF ₃ Et HH Me H 1 SO ₂ CF ₃ Et HHH SOMe 2
SO ₂ CF ₃ Et HH Me H 2 SO ₂ CF ₃ Et HHH SO ₂ Me 0
SO ₂ CF ₃ Et HH CF ₃ H 0 SO ₂ CF ₃ Et HHH SO ₂ Me 1
SO ₂ CF ₃ Et HH CF ₃ H 1 SO ₂ CF ₃ Et HHH SO ₂ Me 2
SO ₂ CF ₃ Et HH CF ₃ H 2 SO ₂ CF ₃ Et HHH OMe 0
SO ₂ CF ₃ Et HH CF ₂ CF ₃ H 0 SO ₂ CF ₃ Et HHH OMe 1
SO ₂ CF ₃ Et HH CF ₂ CF ₃ H 1 SO ₂ CF ₃ Et HHH OMe 2
SO ₂ CF ₃ Et HH CF ₂ CF ₃ H 2 SO ₂ CF ₃ Et HHH OCF ₃ 0
SO ₂ CF ₃ Et HH CF(CF ₃ ) ₂ H 0 SO ₂ CF ₃ Et HHH OCF ₃ 1
SO ₂ CF ₃ Et HH CF(CF ₃ ) ₂ H 1 SO ₂ CF ₃ Et HHH OCF ₃ 2
SO ₂ CF ₃ Et HH CF(CF ₃ ) ₂ H 2 SO ₂ CF ₃ Et HHH NO ₂ 0
――――――――――――――――――― ――――――――――――――――――――
Continuation of [Table 2] Continuation of [Table 2]
――――――――――――――――――― ――――――――――――――――――――
W1 R ¹ Y1 Y2 Y3 Y4 n W1 R ¹ Y1 Y2 Y3 Y4 n
――――――――――――――――――― ――――――――――――――――――――
SO ₂ CF ₃ Et HH SMe H 0 SO ₂ CF ₃ Et HHH NO ₂ 1
SO ₂ CF ₃ Et HH SMe H 1 SO ₂ CF ₃ Et HHH NO ₂ 2
SO ₂ CF ₃ Et HH SMe H 2 SO ₂ CF ₃ Et HHH CN 0
SO ₂ CF ₃ Et HH SOMe H 0 SO ₂ CF ₃ Et HHH CN 1
SO ₂ CF ₃ Et HH SOMe H 1 SO ₂ CF ₃ Et HHH CN 2
SO ₂ CF ₃ Et HH SOMe H 2 SO ₂ CF ₃ Et HFHF 0
SO ₂ CF ₃ Et HH SO ₂ Me H 0 SO ₂ CF ₃ Et HFHF 1
SO ₂ CF ₃ Et HH SO ₂ Me H 1 SO ₂ CF ₃ Et HFHF 2
SO ₂ CF ₃ Et HH SO ₂ Me H 2 SO ₂ CF ₃ Et H Cl H Cl 0
SO ₂ CF ₃ Et HH OMe H 0 SO ₂ CF ₃ Et H Cl H Cl 1
SO ₂ CF ₃ Et HH OMe H 1 SO ₂ CF ₃ Et H Cl H Cl 2
SO ₂ CF ₃ Et HH OMe H 2 SO ₂ CF ₃ Et H Br H Br 0
SO ₂ CF ₃ Et HH OCF ₃ H 0 SO ₂ CF ₃ Et H Br H Br 1
SO ₂ CF ₃ Et HH OCF ₃ H 1 SO ₂ CF ₃ Et H Br H Br 2
SO ₂ CF ₃ Et HH OCF ₃ H 2 SO ₂ CF ₃ Et HIHI 0
SO ₂ CF ₃ Et HH NO ₂ H 0 SO ₂ CF ₃ Et HIHI 1
SO ₂ CF ₃ Et HH NO ₂ H 1 SO ₂ CF ₃ Et HIHI 2
SO ₂ CF ₃ Et HH NO ₂ H 2 SO ₂ CF ₃ Et HFH Cl 0
SO ₂ CF ₃ Et HH CN H 0 SO ₂ CF ₃ Et HFH Cl 1
SO ₂ CF ₃ Et HH CN H 1 SO ₂ CF ₃ Et HFH Cl 2
SO ₂ CF ₃ Et HH CN H 2 SO ₂ CF ₃ Et HFH Br 0
SO ₂ CF ₃ Et HHHF 0 SO ₂ CF ₃ Et HFH Br 1
SO ₂ CF ₃ Et HHHF 1 SO ₂ CF ₃ Et HFH Br 2
SO ₂ CF ₃ Et HHHF 2 SO ₂ CF ₃ Et HFHI 0
SO ₂ CF ₃ Et HHH Cl 0 SO ₂ CF ₃ Et HFHI 1
SO ₂ CF ₃ Et HHH Cl 1 SO ₂ CF ₃ Et HFHI 2
SO ₂ CF ₃ Et HHH Cl 2 SO ₂ CF ₃ Et H Cl HF 0
SO ₂ CF ₃ Et HHH Br 0 SO ₂ CF ₃ Et H Cl HF 1
SO ₂ CF ₃ Et HHH Br 1 SO ₂ CF ₃ Et H Cl HF 2
SO ₂ CF ₃ Et HHH Br 2 SO ₂ CF ₃ Et H Cl H Br 0
SO ₂ CF ₃ Et HHHI 0 SO ₂ CF ₃ Et H Cl H Br 1
SO ₂ CF ₃ Et HHHI 1 SO ₂ CF ₃ Et H Cl H Br 2
――――――――――――――――――― ――――――――――――――――――――
Continuation of [Table 2] Continuation of [Table 2]
――――――――――――――――――― ――――――――――――――――――――
W1 R ¹ Y1 Y2 Y3 Y4 n W1 R ¹ Y1 Y2 Y3 Y4 n
――――――――――――――――――― ――――――――――――――――――――
SO ₂ CF ₃ Et H Cl HI 0 SO ₂ CF ₃ Et HF Cl H 1
SO ₂ CF ₃ Et H Cl HI 1 SO ₂ CF ₃ Et HF Cl H 2
SO ₂ CF ₃ Et H Cl HI 2 SO ₂ CF ₃ Et HF Br H 0
SO ₂ CF ₃ Et H Br HF 0 SO ₂ CF ₃ Et HF Br H 1
SO ₂ CF ₃ Et H Br HF 1 SO ₂ CF ₃ Et HF Br H 2
SO ₂ CF ₃ Et H Br HF 2 SO ₂ CF ₃ Et HFIH 0
SO ₂ CF ₃ Et H Br H Cl 0 SO ₂ CF ₃ Et HFIH 1
SO ₂ CF ₃ Et H Br H Cl 1 SO ₂ CF ₃ Et HFIH 2
SO ₂ CF ₃ Et H Br H Cl 2 SO ₂ CF ₃ Et H Cl FH 0
SO ₂ CF ₃ Et H Br HI 0 SO ₂ CF ₃ Et H Cl FH 1
SO ₂ CF ₃ Et H Br HI 1 SO ₂ CF ₃ Et H Cl FH 2
SO ₂ CF ₃ Et H Br HI 2 SO ₂ CF ₃ Et H Cl Br H 0
SO ₂ CF ₃ Et HIHF 0 SO ₂ CF ₃ Et H Cl Br H 1
SO ₂ CF ₃ Et HIHF 1 SO ₂ CF ₃ Et H Cl Br H 2
SO ₂ CF ₃ Et HIHF 2 SO ₂ CF ₃ Et H Cl IH 0
SO ₂ CF ₃ Et HIH Cl 0 SO ₂ CF ₃ Et H Cl IH 1
SO ₂ CF ₃ Et HIH Cl 1 SO ₂ CF ₃ Et H Cl IH 2
SO ₂ CF ₃ Et HIH Cl 2 SO ₂ CF ₃ Et H Br FH 0
SO ₂ CF ₃ Et HIH Br 0 SO ₂ CF ₃ Et H Br FH 1
SO ₂ CF ₃ Et HIH Br 1 SO ₂ CF ₃ Et H Br FH 2
SO ₂ CF ₃ Et HIH Br 2 SO ₂ CF ₃ Et H Br Cl H 0
SO ₂ CF ₃ Et HFH CN 0 SO ₂ CF ₃ Et H Br Cl H 1
SO ₂ CF ₃ Et HFH CN 1 SO ₂ CF ₃ Et H Br Cl H 2
SO ₂ CF ₃ Et HFH CN 2 SO ₂ CF ₃ Et H Br IH 0
SO ₂ CF ₃ Et H Cl H CN 0 SO ₂ CF ₃ Et H Br IH 1
SO ₂ CF ₃ Et H Cl H CN 1 SO ₂ CF ₃ Et H Br IH 2
SO ₂ CF ₃ Et H Cl H CN 2 SO ₂ CF ₃ Et HIFH 0
SO ₂ CF ₃ Et H Br H CN 0 SO ₂ CF ₃ Et HIFH 1
SO ₂ CF ₃ Et H Br H CN 1 SO ₂ CF ₃ Et HIFH 2
SO ₂ CF ₃ Et H Br H CN 2 SO ₂ CF ₃ Et HI Cl H 0
SO ₂ CF ₃ Et HIH CN 0 SO ₂ CF ₃ Et HI Cl H 1
SO ₂ CF ₃ Et HIH CN 1 SO ₂ CF ₃ Et HI Cl H 2
SO ₂ CF ₃ Et HIH CN 2 SO ₂ CF ₃ Et HI Br H 0
――――――――――――――――――― ――――――――――――――――――――
Continuation of [Table 2] Continuation of [Table 2]
――――――――――――――――――― ――――――――――――――――――――
W1 R ¹ Y1 Y2 Y3 Y4 n W1 R ¹ Y1 Y2 Y3 Y4 n
――――――――――――――――――― ――――――――――――――――――――
SO ₂ CF ₃ Et H CF ₃ HF 0 SO ₂ CF ₃ Et HI Br H 1
SO ₂ CF ₃ Et H CF ₃ HF 1 SO ₂ CF ₃ Et HI Br H 2
SO ₂ CF ₃ Et H CF ₃ HF 2 SO ₂ CF ₃ Et HF CN H 0
SO ₂ CF ₃ Et H CF ₃ H Cl 0 SO ₂ CF ₃ Et HF CN H 1
SO ₂ CF ₃ Et H CF ₃ H Cl 1 SO ₂ CF ₃ Et HF CN H 2
SO ₂ CF ₃ Et H CF ₃ H Cl 2 SO ₂ CF ₃ Et H Cl CN H 0
SO ₂ CF ₃ Et H CF ₃ H Br 0 SO ₂ CF ₃ Et H Cl CN H 1
SO ₂ CF ₃ Et H CF ₃ H Br 1 SO ₂ CF ₃ Et H Cl CN H 2
SO ₂ CF ₃ Et H CF ₃ H Br 2 SO ₂ CF ₃ Et H Br CN H 0
SO ₂ CF ₃ Et H CF ₃ HI 0 SO ₂ CF ₃ Et H Br CN H 1
SO ₂ CF ₃ Et H CF ₃ HI 1 SO ₂ CF ₃ Et H Br CN H 2
SO ₂ CF ₃ Et H CF ₃ HI 2 SO ₂ CF ₃ Et HI CN H 0
SO ₂ CF ₃ Et H CF ₃ H CN 0 SO ₂ CF ₃ Et HI CN H 1
SO ₂ CF ₃ Et H CF ₃ H CN 1 SO ₂ CF ₃ Et HI CN H 2
SO ₂ CF ₃ Et H CF ₃ H CN 2 SO ₂ CF ₃ Et H CF ₃ FH 0
SO ₂ CF ₃ Et HFFH 0 SO ₂ CF ₃ Et H CF ₃ FH 1
SO ₂ CF ₃ Et HFFH 1 SO ₂ CF ₃ Et H CF ₃ FH 2
SO ₂ CF ₃ Et HFFH 2 SO ₂ CF ₃ Et H CF ₃ Cl H 0
SO ₂ CF ₃ Et H Cl Cl H 0 SO ₂ CF ₃ Et H CF ₃ Cl H 1
SO ₂ CF ₃ Et H Cl Cl H 1 SO ₂ CF ₃ Et H CF ₃ Cl H 2
SO ₂ CF ₃ Et H Cl Cl H 2 SO ₂ CF ₃ Et H CF ₃ Br H 0
SO ₂ CF ₃ Et H Br Br H 0 SO ₂ CF ₃ Et H CF ₃ Br H 1
SO ₂ CF ₃ Et H Br Br H 1 SO ₂ CF ₃ Et H CF ₃ Br H 2
SO ₂ CF ₃ Et H Br Br H 2 SO ₂ CF ₃ Et H CF ₃ IH 0
SO ₂ CF ₃ Et HIIH 0 SO ₂ CF ₃ Et H CF ₃ IH 1
SO ₂ CF ₃ Et HIIH 1 SO ₂ CF ₃ Et H CF ₃ IH 2
SO ₂ CF ₃ Et HIIH 2 SO ₂ CF ₃ Et H CF ₃ CN H 0
SO ₂ CF ₃ Et HF Cl H 0 SO ₂ CF ₃ Et H CF ₃ CN H 1
――――――――――――――――――― SO ₂ CF ₃ Et H CF ₃ CN H 2
――――――――――――――――――――
Tables 3 to 13 show specific examples of production intermediates of the fused heterocyclic compound represented by the formula (1) which are included in the present invention and which can be produced using the above method. In the table, Me represents a methyl group and Et represents an ethyl group.
[Table 3]

Continuation of [Table 3] Continuation of [Table 3]―――――――――――――― ――――――――――――
Y1 Y2 Y3 Y4 n Y1 Y2 Y3 Y4 n
――――――――――――― ――――――――――――
HHHH 0 HIHH 1
HHHH 1 HIHH 2
HHHH 2 H Me HH 0
FHHH 0 H Me HH 1
FHHH 1 H Me HH 2
FHHH 2 H CF ₃ HH 0
Cl HHH 0 H CF ₃ HH 1
Cl HHH 1 H CF ₃ HH 2
Cl HHH 2 H CF ₂ CF ₃ HH 0
Br HHH 0 H CF ₂ CF ₃ HH 1
Br HHH 1 H CF ₂ CF ₃ HH 2
Br HHH 2 H CF(CF ₃ ) ₂ HH 0
IHHH 0 H CF(CF ₃ ) ₂ HH 1
IHHH 1 H CF(CF ₃ ) ₂ HH 2
IHHH 2 H SMe HH 0
Me HHH 0 H SMe HH 1
Me HHH 1 H SMe HH 2
Me HHH 2 H SOMe HH 0
CF ₃ HHH 0 H SOMe HH 1
CF ₃ HHH 1 H SOMe HH 2
CF ₃ HHH 2 H SO ₂ Me HH 0
HFHH 0 H SO ₂ Me HH 1
HFHH 1 H SO ₂ Me HH 2
HFHH 2 H OMe HH 0
H Cl HH 0 H OMe HH 1
H Cl HH 1 H OMe HH 2
H Cl HH 2 H OCF ₃ HH 0
H Br HH 0 H OCF ₃ HH 1
H Br HH 1 H OCF ₃ HH 2
H Br HH 2 H NO ₂ HH 0
HIHH 0 ――――――――――――
――――――――――――
Continued from [Table 3] Continued from [Table 3]――――――――――――――――――――――――――
Y1 Y2 Y3 Y4 n Y1 Y2 Y3 Y4 n
――――――――――――――――――――――――――
H NO ₂ HH 1 HHHI 2
H NO ₂ HH 2 HHH Me 0
H CN HH 0 HHH Me 1
H CN HH 1 HHH Me 2
H CN HH 2 HHH CF ₃ 0
HHFH 0 HHH CF ₃ 1
HHFH 1 HHH CF ₃ 2
HHFH 2 HHH CF ₂ CF ₃ 0
HH Cl H 0 HHH CF ₂ CF ₃ 1
HH Cl H 1 HHH CF ₂ CF ₃ 2
HH Cl H 2 HHH CF(CF ₃ ) ₂₀
HH Br H 0 HHH CF(CF ₃ ) ₂ 1
HH Br H 1 HHH CF(CF ₃ ) ₂ 2
HH Br H 2 HHH SMe 0
HHIH 0 HHH SMe 1
HHIH 1 HHH SMe 2
HHIH 2 HHH SOMe 0
HH Me H 0 HHH SOMe 1
HH Me H 1 HHH SOMe 2
HH Me H 2 HHH SO ₂ Me 0
HH CF ₃ H 0 HHH SO ₂ Me 1
HH CF ₃ H 1 HHH SO ₂ Me 2
HH CF ₃ H 2 HHH OMe 0
HH CF ₂ CF ₃ H 0 HHH OMe 1
HH CF ₂ CF ₃ H 1 HHH OMe 2
HH CF ₂ CF ₃ H 2 HHH OCF ₃ 0
HH CF(CF ₃ ) ₂ H 0 HHH OCF ₃ 1
HH CF(CF ₃ ) ₂ H 1 HHH OCF ₃ 2
HH CF(CF ₃ ) ₂ H 2 HHH NO ₂ 0
HH SMe H 0 HHH NO ₂ 1
HH SMe H 1 HHH NO ₂ 2
HH SMe H 2 HHH CN 0
HH SOMe H 0 HHH CN 1
HH SOMe H 1 HHH CN 2
HH SOMe H 2 HFHF 0
HH SO ₂ Me H 0 HFHF 1
HH SO ₂ Me H 1 HFHF 2
HH SO ₂ Me H 2 H Cl H Cl 0
HH OMe H 0 H Cl H Cl 1
HH OMe H 1 H Cl H Cl 2
HH OMe H 2 H Br H Br 0
HH OCF ₃ H 0 H Br H Br 1
HH OCF ₃ H 1 H Br H Br 2
HH OCF ₃ H 2 HIHI 0
HH NO ₂ H 0 HIHI 1
HH NO ₂ H 1 HIHI 2
HH NO ₂ H 2 HFH Cl 0
HH CN H 0 HFH Cl 1
HH CN H 1 HFH Cl 2
HH CN H 2 HFH Br 0
HHHF 0 HFH Br 1
HHHF 1 HFH Br 2
HHHF 2 HFHI 0
HHH Cl 0 HFHI 1
HHH Cl 1 HFHI 2
HHH Cl 2 H Cl HF 0
HHH Br 0 H Cl HF 1
HHH Br 1 H Cl HF 2
HHH Br 2 H Cl H Br 0
HHHI 0 H Cl H Br 1
HHHI 1 H Cl H Br 2
―――――――――――― ――――――――――――
Continuation of [Table 3] Continuation of [Table 3]――――――――――――――――――――――――――
Y1 Y2 Y3 Y4 n Y1 Y2 Y3 Y4 n
――――――――――――――――――――――――――
H Cl HI 0 HF Cl H 1
H Cl HI 1 HF Cl H 2
H Cl HI 2 HF Br H 0
H Br HF 0 HF Br H 1
H Br HF 1 HF Br H 2
H Br HF 2 HFIH 0
H Br H Cl 0 HFIH 1
H Br H Cl 1 HFIH 2
H Br H Cl 2 H Cl FH 0
H Br HI 0 H Cl FH 1
H Br HI 1 H Cl FH 2
H Br HI 2 H Cl Br H 0
HIHF 0 H Cl Br H 1
HIHF 1 H Cl Br H 2
HIHF 2 H Cl IH 0
HIH Cl 0 H Cl IH 1
HIH Cl 1 H Cl IH 2
HIH Cl 2 H Br FH 0
HIH Br 0 H Br FH 1
HIH Br 1 H Br FH 2
HIH Br 2 H Br Cl H 0
HFH CN 0 H Br Cl H 1
HFH CN 1 H Br Cl H 2
HFH CN 2 H Br IH 0
H Cl H CN 0 H Br IH 1
H Cl H CN 1 H Br IH 2
H Cl H CN 2 HIFH 0
H Br H CN 0 HIFH 1
H Br H CN 1 HIFH 2
H Br H CN 2 HI Cl H 0
HIH CN 0 HI Cl H 1
HIH CN 1 HI Cl H 2
HIH CN 2 HI Br H 0
――――――――――――――――――――――――――
Continuation of [Table 3] Continuation of [Table 3]――――――――――――――――――――――――――
Y1 Y2 Y3 Y4 n Y1 Y2 Y3 Y4 n
――――――――――――――――――――――――――
H CF ₃ HF 0 HI Br H 1
H CF ₃ HF 1 HI Br H 2
H CF ₃ HF 2 HF CN H 0
H CF ₃ H Cl 0 HF CN H 1
H CF ₃ H Cl 1 HF CN H 2
H CF ₃ H Cl 2 H Cl CN H 0
H CF ₃ H Br 0 H Cl CN H 1
H CF ₃ H Br 1 H Cl CN H 2
H CF ₃ H Br 2 H Br CN H 0
H CF ₃ HI 0 H Br CN H 1
H CF ₃ HI 1 H Br CN H 2
H CF ₃ HI 2 HI CN H 0
H CF ₃ H CN 0 HI CN H 1
H CF ₃ H CN 1 HI CN H 2
H CF ₃ H CN 2 H CF ₃ FH 0
HFFH 0 H CF ₃ FH 1
HFFH 1 H CF ₃ FH 2
HFFH 2 H CF ₃ Cl H 0
H Cl Cl H 0 H CF ₃ Cl H 1
H Cl Cl H 1 H CF ₃ Cl H 2
H Cl Cl H 2 H CF ₃ Br H 0
H Br Br H 0 H CF ₃ Br H 1
H Br Br H 1 H CF ₃ Br H 2
H Br Br H 2 H CF ₃ IH 0
HIIH 0 H CF ₃ IH 1
HIIH 1 H CF ₃ IH 2
HIIH 2 H CF ₃ CN H 0
HF Cl H 0 H CF ₃ CN H 1
―――――――――――― H CF ₃ CN H 2
―――――――――――――
[Table 4]

Continuation of [Table 4] Continuation of [Table 4] ――――――――――――― ――――――――――――
Y1 Y2 Y3 Y4 n Y1 Y2 Y3 Y4 n
――――――――――――― ――――――――――――
HHHH 0 HIHH 1
HHHH 1 HIHH 2
HHHH 2 H Me HH 0
FHHH 0 H Me HH 1
FHHH 1 H Me HH 2
FHHH 2 H CF ₃ HH 0
Cl HHH 0 H CF ₃ HH 1
Cl HHH 1 H CF ₃ HH 2
Cl HHH 2 H CF ₂ CF ₃ HH 0
Br HHH 0 H CF ₂ CF ₃ HH 1
Br HHH 1 H CF ₂ CF ₃ HH 2
Br HHH 2 H CF(CF ₃ ) ₂ HH 0
IHHH 0 H CF(CF ₃ ) ₂ HH 1
IHHH 1 H CF(CF ₃ ) ₂ HH 2
IHHH 2 H SMe HH 0
Me HHH 0 H SMe HH 1
Me HHH 1 H SMe HH 2
Me HHH 2 H SOMe HH 0
CF ₃ HHH 0 H SOMe HH 1
CF ₃ HHH 1 H SOMe HH 2
CF ₃ HHH 2 H SO ₂ Me HH 0
HFHH 0 H SO ₂ Me HH 1
HFHH 1 H SO ₂ Me HH 2
HFHH 2 H OMe HH 0
H Cl HH 0 H OMe HH 1
H Cl HH 1 H OMe HH 2
H Cl HH 2 H OCF ₃ HH 0
H Br HH 0 H OCF ₃ HH 1
H Br HH 1 H OCF ₃ HH 2
H Br HH 2 H NO ₂ HH 0
HIHH 0 ――――――――――――
――――――――――――
Continuation of [Table 4] Continuation of [Table 4]――――――――――――――――――――――――――
Y1 Y2 Y3 Y4 n Y1 Y2 Y3 Y4 n
――――――――――――――――――――――――――
H NO ₂ HH 1 HHHI 2
H NO ₂ HH 2 HHH Me 0
H CN HH 0 HHH Me 1
H CN HH 1 HHH Me 2
H CN HH 2 HHH CF ₃ 0
HHFH 0 HHH CF ₃ 1
HHFH 1 HHH CF ₃ 2
HHFH 2 HHH CF ₂ CF ₃ 0
HH Cl H 0 HHH CF ₂ CF ₃ 1
HH Cl H 1 HHH CF ₂ CF ₃ 2
HH Cl H 2 HHH CF(CF ₃ ) ₂₀
HH Br H 0 HHH CF(CF ₃ ) ₂ 1
HH Br H 1 HHH CF(CF ₃ ) ₂ 2
HH Br H 2 HHH SMe 0
HHIH 0 HHH SMe 1
HHIH 1 HHH SMe 2
HHIH 2 HHH SOMe 0
HH Me H 0 HHH SOMe 1
HH Me H 1 HHH SOMe 2
HH Me H 2 HHH SO ₂ Me 0
HH CF ₃ H 0 HHH SO ₂ Me 1
HH CF ₃ H 1 HHH SO ₂ Me 2
HH CF ₃ H 2 HHH OMe 0
HH CF ₂ CF ₃ H 0 HHH OMe 1
HH CF ₂ CF ₃ H 1 HHH OMe 2
HH CF ₂ CF ₃ H 2 HHH OCF ₃ 0
HH CF(CF ₃ ) ₂ H 0 HHH OCF ₃ 1
HH CF(CF ₃ ) ₂ H 1 HHH OCF ₃ 2
HH CF(CF ₃ ) ₂ H 2 HHH NO ₂ 0
HH SMe H 0 HHH NO ₂ 1
HH SMe H 1 HHH NO ₂ 2
HH SMe H 2 HHH CN 0
HH SOMe H 0 HHH CN 1
HH SOMe H 1 HHH CN 2
HH SOMe H 2 HFHF 0
HH SO ₂ Me H 0 HFHF 1
HH SO ₂ Me H 1 HFHF 2
HH SO ₂ Me H 2 H Cl H Cl 0
HH OMe H 0 H Cl H Cl 1
HH OMe H 1 H Cl H Cl 2
HH OMe H 2 H Br H Br 0
HH OCF ₃ H 0 H Br H Br 1
HH OCF ₃ H 1 H Br H Br 2
HH OCF ₃ H 2 HIHI 0
HH NO ₂ H 0 HIHI 1
HH NO ₂ H 1 HIHI 2
HH NO ₂ H 2 HFH Cl 0
HH CN H 0 HFH Cl 1
HH CN H 1 HFH Cl 2
HH CN H 2 HFH Br 0
HHHF 0 HFH Br 1
HHHF 1 HFH Br 2
HHHF 2 HFHI 0
HHH Cl 0 HFHI 1
HHH Cl 1 HFHI 2
HHH Cl 2 H Cl HF 0
HHH Br 0 H Cl HF 1
HHH Br 1 H Cl HF 2
HHH Br 2 H Cl H Br 0
HHHI 0 H Cl H Br 1
HHHI 1 H Cl H Br 2
―――――――――――― ――――――――――――
Continuation of [Table 4] Continuation of [Table 4]――――――――――――――――――――――――――
Y1 Y2 Y3 Y4 n Y1 Y2 Y3 Y4 n
――――――――――――――――――――――――――
H Cl HI 0 HF Cl H 1
H Cl HI 1 HF Cl H 2
H Cl HI 2 HF Br H 0
H Br HF 0 HF Br H 1
H Br HF 1 HF Br H 2
H Br HF 2 HFIH 0
H Br H Cl 0 HFIH 1
H Br H Cl 1 HFIH 2
H Br H Cl 2 H Cl FH 0
H Br HI 0 H Cl FH 1
H Br HI 1 H Cl FH 2
H Br HI 2 H Cl Br H 0
HIHF 0 H Cl Br H 1
HIHF 1 H Cl Br H 2
HIHF 2 H Cl IH 0
HIH Cl 0 H Cl IH 1
HIH Cl 1 H Cl IH 2
HIH Cl 2 H Br FH 0
HIH Br 0 H Br FH 1
HIH Br 1 H Br FH 2
HIH Br 2 H Br Cl H 0
HFH CN 0 H Br Cl H 1
HFH CN 1 H Br Cl H 2
HFH CN 2 H Br IH 0
H Cl H CN 0 H Br IH 1
H Cl H CN 1 H Br IH 2
H Cl H CN 2 HIFH 0
H Br H CN 0 HIFH 1
H Br H CN 1 HIFH 2
H Br H CN 2 HI Cl H 0
HIH CN 0 HI Cl H 1
HIH CN 1 HI Cl H 2
HIH CN 2 HI Br H 0
――――――――――――――――――――――――――
Continuation of [Table 4] Continuation of [Table 4]――――――――――――――――――――――――――
Y1 Y2 Y3 Y4 n Y1 Y2 Y3 Y4 n
――――――――――――――――――――――――――
H CF ₃ HF 0 HI Br H 1
H CF ₃ HF 1 HI Br H 2
H CF ₃ HF 2 HF CN H 0
H CF ₃ H Cl 0 HF CN H 1
H CF ₃ H Cl 1 HF CN H 2
H CF ₃ H Cl 2 H Cl CN H 0
H CF ₃ H Br 0 H Cl CN H 1
H CF ₃ H Br 1 H Cl CN H 2
H CF ₃ H Br 2 H Br CN H 0
H CF ₃ HI 0 H Br CN H 1
H CF ₃ HI 1 H Br CN H 2
H CF ₃ HI 2 HI CN H 0
H CF ₃ H CN 0 HI CN H 1
H CF ₃ H CN 1 HI CN H 2
H CF ₃ H CN 2 H CF ₃ FH 0
HFFH 0 H CF ₃ FH 1
HFFH 1 H CF ₃ FH 2
HFFH 2 H CF ₃ Cl H 0
H Cl Cl H 0 H CF ₃ Cl H 1
H Cl Cl H 1 H CF ₃ Cl H 2
H Cl Cl H 2 H CF ₃ Br H 0
H Br Br H 0 H CF ₃ Br H 1
H Br Br H 1 H CF ₃ Br H 2
H Br Br H 2 H CF ₃ IH 0
HIIH 0 H CF ₃ IH 1
HIIH 1 H CF ₃ IH 2
HIIH 2 H CF ₃ CN H 0
HF Cl H 0 H CF ₃ CN H 1
―――――――――――― H CF ₃ CN H 2
―――――――――――――
[Table 5]

Continuation of [Table 5] Continuation of [Table 5] ――――――――――――― ――――――――――――
Y1 Y2 Y3 Y4 n Y1 Y2 Y3 Y4 n
――――――――――――― ――――――――――――
HHHH 0 HIHH 1
HHHH 1 HIHH 2
HHHH 2 H Me HH 0
FHHH 0 H Me HH 1
FHHH 1 H Me HH 2
FHHH 2 H CF ₃ HH 0
Cl HHH 0 H CF ₃ HH 1
Cl HHH 1 H CF ₃ HH 2
Cl HHH 2 H CF ₂ CF ₃ HH 0
Br HHH 0 H CF ₂ CF ₃ HH 1
Br HHH 1 H CF ₂ CF ₃ HH 2
Br HHH 2 H CF(CF ₃ ) ₂ HH 0
IHHH 0 H CF(CF ₃ ) ₂ HH 1
IHHH 1 H CF(CF ₃ ) ₂ HH 2
IHHH 2 H SMe HH 0
Me HHH 0 H SMe HH 1
Me HHH 1 H SMe HH 2
Me HHH 2 H SOMe HH 0
CF ₃ HHH 0 H SOMe HH 1
CF ₃ HHH 1 H SOMe HH 2
CF ₃ HHH 2 H SO ₂ Me HH 0
HFHH 0 H SO ₂ Me HH 1
HFHH 1 H SO ₂ Me HH 2
HFHH 2 H OMe HH 0
H Cl HH 0 H OMe HH 1
H Cl HH 1 H OMe HH 2
H Cl HH 2 H OCF ₃ HH 0
H Br HH 0 H OCF ₃ HH 1
H Br HH 1 H OCF ₃ HH 2
H Br HH 2 H NO ₂ HH 0
HIHH 0 ――――――――――――
――――――――――――
Continuation of [Table 5] Continuation of [Table 5]――――――――――――――――――――――――――
Y1 Y2 Y3 Y4 n Y1 Y2 Y3 Y4 n
――――――――――――――――――――――――――
H NO ₂ HH 1 HHHI 2
H NO ₂ HH 2 HHH Me 0
H CN HH 0 HHH Me 1
H CN HH 1 HHH Me 2
H CN HH 2 HHH CF ₃ 0
HHFH 0 HHH CF ₃ 1
HHFH 1 HHH CF ₃ 2
HHFH 2 HHH CF ₂ CF ₃ 0
HH Cl H 0 HHH CF ₂ CF ₃ 1
HH Cl H 1 HHH CF ₂ CF ₃ 2
HH Cl H 2 HHH CF(CF ₃ ) ₂₀
HH Br H 0 HHH CF(CF ₃ ) ₂ 1
HH Br H 1 HHH CF(CF ₃ ) ₂ 2
HH Br H 2 HHH SMe 0
HHIH 0 HHH SMe 1
HHIH 1 HHH SMe 2
HHIH 2 HHH SOMe 0
HH Me H 0 HHH SOMe 1
HH Me H 1 HHH SOMe 2
HH Me H 2 HHH SO ₂ Me 0
HH CF ₃ H 0 HHH SO ₂ Me 1
HH CF ₃ H 1 HHH SO ₂ Me 2
HH CF ₃ H 2 HHH OMe 0
HH CF ₂ CF ₃ H 0 HHH OMe 1
HH CF ₂ CF ₃ H 1 HHH OMe 2
HH CF ₂ CF ₃ H 2 HHH OCF ₃ 0
HH CF(CF ₃ ) ₂ H 0 HHH OCF ₃ 1
HH CF(CF ₃ ) ₂ H 1 HHH OCF ₃ 2
HH CF(CF ₃ ) ₂ H 2 HHH NO ₂ 0
HH SMe H 0 HHH NO ₂ 1
HH SMe H 1 HHH NO ₂ 2
HH SMe H 2 HHH CN 0
HH SOMe H 0 HHH CN 1
HH SOMe H 1 HHH CN 2
HH SOMe H 2 HFHF 0
HH SO ₂ Me H 0 HFHF 1
HH SO ₂ Me H 1 HFHF 2
HH SO ₂ Me H 2 H Cl H Cl 0
HH OMe H 0 H Cl H Cl 1
HH OMe H 1 H Cl H Cl 2
HH OMe H 2 H Br H Br 0
HH OCF ₃ H 0 H Br H Br 1
HH OCF ₃ H 1 H Br H Br 2
HH OCF ₃ H 2 HIHI 0
HH NO ₂ H 0 HIHI 1
HH NO ₂ H 1 HIHI 2
HH NO ₂ H 2 HFH Cl 0
HH CN H 0 HFH Cl 1
HH CN H 1 HFH Cl 2
HH CN H 2 HFH Br 0
HHHF 0 HFH Br 1
HHHF 1 HFH Br 2
HHHF 2 HFHI 0
HHH Cl 0 HFHI 1
HHH Cl 1 HFHI 2
HHH Cl 2 H Cl HF 0
HHH Br 0 H Cl HF 1
HHH Br 1 H Cl HF 2
HHH Br 2 H Cl H Br 0
HHHI 0 H Cl H Br 1
HHHI 1 H Cl H Br 2
―――――――――――― ――――――――――――
Continuation of [Table 5] Continuation of [Table 5]――――――――――――――――――――――――――
Y1 Y2 Y3 Y4 n Y1 Y2 Y3 Y4 n
――――――――――――――――――――――――――
H Cl HI 0 HF Cl H 1
H Cl HI 1 HF Cl H 2
H Cl HI 2 HF Br H 0
H Br HF 0 HF Br H 1
H Br HF 1 HF Br H 2
H Br HF 2 HFIH 0
H Br H Cl 0 HFIH 1
H Br H Cl 1 HFIH 2
H Br H Cl 2 H Cl FH 0
H Br HI 0 H Cl FH 1
H Br HI 1 H Cl FH 2
H Br HI 2 H Cl Br H 0
HIHF 0 H Cl Br H 1
HIHF 1 H Cl Br H 2
HIHF 2 H Cl IH 0
HIH Cl 0 H Cl IH 1
HIH Cl 1 H Cl IH 2
HIH Cl 2 H Br FH 0
HIH Br 0 H Br FH 1
HIH Br 1 H Br FH 2
HIH Br 2 H Br Cl H 0
HFH CN 0 H Br Cl H 1
HFH CN 1 H Br Cl H 2
HFH CN 2 H Br IH 0
H Cl H CN 0 H Br IH 1
H Cl H CN 1 H Br IH 2
H Cl H CN 2 HIFH 0
H Br H CN 0 HIFH 1
H Br H CN 1 HIFH 2
H Br H CN 2 HI Cl H 0
HIH CN 0 HI Cl H 1
HIH CN 1 HI Cl H 2
HIH CN 2 HI Br H 0
――――――――――――――――――――――――――
Continuation of [Table 5] Continuation of [Table 5]――――――――――――――――――――――――――
Y1 Y2 Y3 Y4 n Y1 Y2 Y3 Y4 n
――――――――――――――――――――――――――
H CF ₃ HF 0 HI Br H 1
H CF ₃ HF 1 HI Br H 2
H CF ₃ HF 2 HF CN H 0
H CF ₃ H Cl 0 HF CN H 1
H CF ₃ H Cl 1 HF CN H 2
H CF ₃ H Cl 2 H Cl CN H 0
H CF ₃ H Br 0 H Cl CN H 1
H CF ₃ H Br 1 H Cl CN H 2
H CF ₃ H Br 2 H Br CN H 0
H CF ₃ HI 0 H Br CN H 1
H CF ₃ HI 1 H Br CN H 2
H CF ₃ HI 2 HI CN H 0
H CF ₃ H CN 0 HI CN H 1
H CF ₃ H CN 1 HI CN H 2
H CF ₃ H CN 2 H CF ₃ FH 0
HFFH 0 H CF ₃ FH 1
HFFH 1 H CF ₃ FH 2
HFFH 2 H CF ₃ Cl H 0
H Cl Cl H 0 H CF ₃ Cl H 1
H Cl Cl H 1 H CF ₃ Cl H 2
H Cl Cl H 2 H CF ₃ Br H 0
H Br Br H 0 H CF ₃ Br H 1
H Br Br H 1 H CF ₃ Br H 2
H Br Br H 2 H CF ₃ IH 0
HIIH 0 H CF ₃ IH 1
HIIH 1 H CF ₃ IH 2
HIIH 2 H CF ₃ CN H 0
HF Cl H 0 H CF ₃ CN H 1
―――――――――――― H CF ₃ CN H 2
―――――――――――――

[Table 6]

Continuation of [Table 6] Continuation of [Table 6] ――――――――――――― ――――――――――――
Y1 Y2 Y3 Y4 n Y1 Y2 Y3 Y4 n
――――――――――――― ――――――――――――
HHHH 0 HIHH 1
HHHH 1 HIHH 2
HHHH 2 H Me HH 0
FHHH 0 H Me HH 1
FHHH 1 H Me HH 2
FHHH 2 H CF ₃ HH 0
Cl HHH 0 H CF ₃ HH 1
Cl HHH 1 H CF ₃ HH 2
Cl HHH 2 H CF ₂ CF ₃ HH 0
Br HHH 0 H CF ₂ CF ₃ HH 1
Br HHH 1 H CF ₂ CF ₃ HH 2
Br HHH 2 H CF(CF ₃ ) ₂ HH 0
IHHH 0 H CF(CF ₃ ) ₂ HH 1
IHHH 1 H CF(CF ₃ ) ₂ HH 2
IHHH 2 H SMe HH 0
Me HHH 0 H SMe HH 1
Me HHH 1 H SMe HH 2
Me HHH 2 H SOMe HH 0
CF ₃ HHH 0 H SOMe HH 1
CF ₃ HHH 1 H SOMe HH 2
CF ₃ HHH 2 H SO ₂ Me HH 0
HFHH 0 H SO ₂ Me HH 1
HFHH 1 H SO ₂ Me HH 2
HFHH 2 H OMe HH 0
H Cl HH 0 H OMe HH 1
H Cl HH 1 H OMe HH 2
H Cl HH 2 H OCF ₃ HH 0
H Br HH 0 H OCF ₃ HH 1
H Br HH 1 H OCF ₃ HH 2
H Br HH 2 H NO ₂ HH 0
HIHH 0 ――――――――――――
――――――――――――
Continuation of [Table 6] Continuation of [Table 6]――――――――――――――――――――――――――
Y1 Y2 Y3 Y4 n Y1 Y2 Y3 Y4 n
――――――――――――――――――――――――――
H NO ₂ HH 1 HHHI 2
H NO ₂ HH 2 HHH Me 0
H CN HH 0 HHH Me 1
H CN HH 1 HHH Me 2
H CN HH 2 HHH CF ₃ 0
HHFH 0 HHH CF ₃ 1
HHFH 1 HHH CF ₃ 2
HHFH 2 HHH CF ₂ CF ₃ 0
HH Cl H 0 HHH CF ₂ CF ₃ 1
HH Cl H 1 HHH CF ₂ CF ₃ 2
HH Cl H 2 HHH CF(CF ₃ ) ₂₀
HH Br H 0 HHH CF(CF ₃ ) ₂ 1
HH Br H 1 HHH CF(CF ₃ ) ₂ 2
HH Br H 2 HHH SMe 0
HHIH 0 HHH SMe 1
HHIH 1 HHH SMe 2
HHIH 2 HHH SOMe 0
HH Me H 0 HHH SOMe 1
HH Me H 1 HHH SOMe 2
HH Me H 2 HHH SO ₂ Me 0
HH CF ₃ H 0 HHH SO ₂ Me 1
HH CF ₃ H 1 HHH SO ₂ Me 2
HH CF ₃ H 2 HHH OMe 0
HH CF ₂ CF ₃ H 0 HHH OMe 1
HH CF ₂ CF ₃ H 1 HHH OMe 2
HH CF ₂ CF ₃ H 2 HHH OCF ₃ 0
HH CF(CF ₃ ) ₂ H 0 HHH OCF ₃ 1
HH CF(CF ₃ ) ₂ H 1 HHH OCF ₃ 2
HH CF(CF ₃ ) ₂ H 2 HHH NO ₂ 0
HH SMe H 0 HHH NO ₂ 1
HH SMe H 1 HHH NO ₂ 2
HH SMe H 2 HHH CN 0
HH SOMe H 0 HHH CN 1
HH SOMe H 1 HHH CN 2
HH SOMe H 2 HFHF 0
HH SO ₂ Me H 0 HFHF 1
HH SO ₂ Me H 1 HFHF 2
HH SO ₂ Me H 2 H Cl H Cl 0
HH OMe H 0 H Cl H Cl 1
HH OMe H 1 H Cl H Cl 2
HH OMe H 2 H Br H Br 0
HH OCF ₃ H 0 H Br H Br 1
HH OCF ₃ H 1 H Br H Br 2
HH OCF ₃ H 2 HIHI 0
HH NO ₂ H 0 HIHI 1
HH NO ₂ H 1 HIHI 2
HH NO ₂ H 2 HFH Cl 0
HH CN H 0 HFH Cl 1
HH CN H 1 HFH Cl 2
HH CN H 2 HFH Br 0
HHHF 0 HFH Br 1
HHHF 1 HFH Br 2
HHHF 2 HFHI 0
HHH Cl 0 HFHI 1
HHH Cl 1 HFHI 2
HHH Cl 2 H Cl HF 0
HHH Br 0 H Cl HF 1
HHH Br 1 H Cl HF 2
HHH Br 2 H Cl H Br 0
HHHI 0 H Cl H Br 1
HHHI 1 H Cl H Br 2
―――――――――――― ――――――――――――
Continuation of [Table 6] Continuation of [Table 6]――――――――――――――――――――――――――
Y1 Y2 Y3 Y4 n Y1 Y2 Y3 Y4 n
――――――――――――――――――――――――――
H Cl HI 0 HF Cl H 1
H Cl HI 1 HF Cl H 2
H Cl HI 2 HF Br H 0
H Br HF 0 HF Br H 1
H Br HF 1 HF Br H 2
H Br HF 2 HFIH 0
H Br H Cl 0 HFIH 1
H Br H Cl 1 HFIH 2
H Br H Cl 2 H Cl FH 0
H Br HI 0 H Cl FH 1
H Br HI 1 H Cl FH 2
H Br HI 2 H Cl Br H 0
HIHF 0 H Cl Br H 1
HIHF 1 H Cl Br H 2
HIHF 2 H Cl IH 0
HIH Cl 0 H Cl IH 1
HIH Cl 1 H Cl IH 2
HIH Cl 2 H Br FH 0
HIH Br 0 H Br FH 1
HIH Br 1 H Br FH 2
HIH Br 2 H Br Cl H 0
HFH CN 0 H Br Cl H 1
HFH CN 1 H Br Cl H 2
HFH CN 2 H Br IH 0
H Cl H CN 0 H Br IH 1
H Cl H CN 1 H Br IH 2
H Cl H CN 2 HIFH 0
H Br H CN 0 HIFH 1
H Br H CN 1 HIFH 2
H Br H CN 2 HI Cl H 0
HIH CN 0 HI Cl H 1
HIH CN 1 HI Cl H 2
HIH CN 2 HI Br H 0
――――――――――――――――――――――――――
Continuation of [Table 6] Continuation of [Table 6]――――――――――――――――――――――――――
Y1 Y2 Y3 Y4 n Y1 Y2 Y3 Y4 n
――――――――――――――――――――――――――
H CF ₃ HF 0 HI Br H 1
H CF ₃ HF 1 HI Br H 2
H CF ₃ HF 2 HF CN H 0
H CF ₃ H Cl 0 HF CN H 1
H CF ₃ H Cl 1 HF CN H 2
H CF ₃ H Cl 2 H Cl CN H 0
H CF ₃ H Br 0 H Cl CN H 1
H CF ₃ H Br 1 H Cl CN H 2
H CF ₃ H Br 2 H Br CN H 0
H CF ₃ HI 0 H Br CN H 1
H CF ₃ HI 1 H Br CN H 2
H CF ₃ HI 2 HI CN H 0
H CF ₃ H CN 0 HI CN H 1
H CF ₃ H CN 1 HI CN H 2
H CF ₃ H CN 2 H CF ₃ FH 0
HFFH 0 H CF ₃ FH 1
HFFH 1 H CF ₃ FH 2
HFFH 2 H CF ₃ Cl H 0
H Cl Cl H 0 H CF ₃ Cl H 1
H Cl Cl H 1 H CF ₃ Cl H 2
H Cl Cl H 2 H CF ₃ Br H 0
H Br Br H 0 H CF ₃ Br H 1
H Br Br H 1 H CF ₃ Br H 2
H Br Br H 2 H CF ₃ IH 0
HIIH 0 H CF ₃ IH 1
HIIH 1 H CF ₃ IH 2
HIIH 2 H CF ₃ CN H 0
HF Cl H 0 H CF ₃ CN H 1
―――――――――――― H CF ₃ CN H 2
―――――――――――――
[Table 7]

Continuation of [Table 7] Continuation of [Table 7] ――――――――――――― ――――――――――――
Y1 Y2 Y3 Y4 n Y1 Y2 Y3 Y4 n
――――――――――――― ――――――――――――
HHHH 0 HIHH 1
HHHH 1 HIHH 2
HHHH 2 H Me HH 0
FHHH 0 H Me HH 1
FHHH 1 H Me HH 2
FHHH 2 H CF ₃ HH 0
Cl HHH 0 H CF ₃ HH 1
Cl HHH 1 H CF ₃ HH 2
Cl HHH 2 H CF ₂ CF ₃ HH 0
Br HHH 0 H CF ₂ CF ₃ HH 1
Br HHH 1 H CF ₂ CF ₃ HH 2
Br HHH 2 H CF(CF ₃ ) ₂ HH 0
IHHH 0 H CF(CF ₃ ) ₂ HH 1
IHHH 1 H CF(CF ₃ ) ₂ HH 2
IHHH 2 H SMe HH 0
Me HHH 0 H SMe HH 1
Me HHH 1 H SMe HH 2
Me HHH 2 H SOMe HH 0
CF ₃ HHH 0 H SOMe HH 1
CF ₃ HHH 1 H SOMe HH 2
CF ₃ HHH 2 H SO ₂ Me HH 0
HFHH 0 H SO ₂ Me HH 1
HFHH 1 H SO ₂ Me HH 2
HFHH 2 H OMe HH 0
H Cl HH 0 H OMe HH 1
H Cl HH 1 H OMe HH 2
H Cl HH 2 H OCF ₃ HH 0
H Br HH 0 H OCF ₃ HH 1
H Br HH 1 H OCF ₃ HH 2
H Br HH 2 H NO ₂ HH 0
HIHH 0 ――――――――――――
――――――――――――
Continued from [Table 7] Continued from [Table 7]――――――――――――――――――――――――――
Y1 Y2 Y3 Y4 n Y1 Y2 Y3 Y4 n
――――――――――――――――――――――――――
H NO ₂ HH 1 HHHI 2
H NO ₂ HH 2 HHH Me 0
H CN HH 0 HHH Me 1
H CN HH 1 HHH Me 2
H CN HH 2 HHH CF ₃ 0
HHFH 0 HHH CF ₃ 1
HHFH 1 HHH CF ₃ 2
HHFH 2 HHH CF ₂ CF ₃ 0
HH Cl H 0 HHH CF ₂ CF ₃ 1
HH Cl H 1 HHH CF ₂ CF ₃ 2
HH Cl H 2 HHH CF(CF ₃ ) ₂₀
HH Br H 0 HHH CF(CF ₃ ) ₂ 1
HH Br H 1 HHH CF(CF ₃ ) ₂ 2
HH Br H 2 HHH SMe 0
HHIH 0 HHH SMe 1
HHIH 1 HHH SMe 2
HHIH 2 HHH SOMe 0
HH Me H 0 HHH SOMe 1
HH Me H 1 HHH SOMe 2
HH Me H 2 HHH SO ₂ Me 0
HH CF ₃ H 0 HHH SO ₂ Me 1
HH CF ₃ H 1 HHH SO ₂ Me 2
HH CF ₃ H 2 HHH OMe 0
HH CF ₂ CF ₃ H 0 HHH OMe 1
HH CF ₂ CF ₃ H 1 HHH OMe 2
HH CF ₂ CF ₃ H 2 HHH OCF ₃ 0
HH CF(CF ₃ ) ₂ H 0 HHH OCF ₃ 1
HH CF(CF ₃ ) ₂ H 1 HHH OCF ₃ 2
HH CF(CF ₃ ) ₂ H 2 HHH NO ₂ 0
HH SMe H 0 HHH NO ₂ 1
HH SMe H 1 HHH NO ₂ 2
HH SMe H 2 HHH CN 0
HH SOMe H 0 HHH CN 1
HH SOMe H 1 HHH CN 2
HH SOMe H 2 HFHF 0
HH SO ₂ Me H 0 HFHF 1
HH SO ₂ Me H 1 HFHF 2
HH SO ₂ Me H 2 H Cl H Cl 0
HH OMe H 0 H Cl H Cl 1
HH OMe H 1 H Cl H Cl 2
HH OMe H 2 H Br H Br 0
HH OCF ₃ H 0 H Br H Br 1
HH OCF ₃ H 1 H Br H Br 2
HH OCF ₃ H 2 HIHI 0
HH NO ₂ H 0 HIHI 1
HH NO ₂ H 1 HIHI 2
HH NO ₂ H 2 HFH Cl 0
HH CN H 0 HFH Cl 1
HH CN H 1 HFH Cl 2
HH CN H 2 HFH Br 0
HHHF 0 HFH Br 1
HHHF 1 HFH Br 2
HHHF 2 HFHI 0
HHH Cl 0 HFHI 1
HHH Cl 1 HFHI 2
HHH Cl 2 H Cl HF 0
HHH Br 0 H Cl HF 1
HHH Br 1 H Cl HF 2
HHH Br 2 H Cl H Br 0
HHHI 0 H Cl H Br 1
HHHI 1 H Cl H Br 2
―――――――――――― ――――――――――――
Continuation of [Table 7] Continuation of [Table 7]――――――――――――――――――――――――――
Y1 Y2 Y3 Y4 n Y1 Y2 Y3 Y4 n
――――――――――――――――――――――――――
H Cl HI 0 HF Cl H 1
H Cl HI 1 HF Cl H 2
H Cl HI 2 HF Br H 0
H Br HF 0 HF Br H 1
H Br HF 1 HF Br H 2
H Br HF 2 HFIH 0
H Br H Cl 0 HFIH 1
H Br H Cl 1 HFIH 2
H Br H Cl 2 H Cl FH 0
H Br HI 0 H Cl FH 1
H Br HI 1 H Cl FH 2
H Br HI 2 H Cl Br H 0
HIHF 0 H Cl Br H 1
HIHF 1 H Cl Br H 2
HIHF 2 H Cl IH 0
HIH Cl 0 H Cl IH 1
HIH Cl 1 H Cl IH 2
HIH Cl 2 H Br FH 0
HIH Br 0 H Br FH 1
HIH Br 1 H Br FH 2
HIH Br 2 H Br Cl H 0
HFH CN 0 H Br Cl H 1
HFH CN 1 H Br Cl H 2
HFH CN 2 H Br IH 0
H Cl H CN 0 H Br IH 1
H Cl H CN 1 H Br IH 2
H Cl H CN 2 HIFH 0
H Br H CN 0 HIFH 1
H Br H CN 1 HIFH 2
H Br H CN 2 HI Cl H 0
HIH CN 0 HI Cl H 1
HIH CN 1 HI Cl H 2
HIH CN 2 HI Br H 0
――――――――――――――――――――――――――
Continuation of [Table 7] Continuation of [Table 7]――――――――――――――――――――――――――
Y1 Y2 Y3 Y4 n Y1 Y2 Y3 Y4 n
――――――――――――――――――――――――――
H CF ₃ HF 0 HI Br H 1
H CF ₃ HF 1 HI Br H 2
H CF ₃ HF 2 HF CN H 0
H CF ₃ H Cl 0 HF CN H 1
H CF ₃ H Cl 1 HF CN H 2
H CF ₃ H Cl 2 H Cl CN H 0
H CF ₃ H Br 0 H Cl CN H 1
H CF ₃ H Br 1 H Cl CN H 2
H CF ₃ H Br 2 H Br CN H 0
H CF ₃ HI 0 H Br CN H 1
H CF ₃ HI 1 H Br CN H 2
H CF ₃ HI 2 HI CN H 0
H CF ₃ H CN 0 HI CN H 1
H CF ₃ H CN 1 HI CN H 2
H CF ₃ H CN 2 H CF ₃ FH 0
HFFH 0 H CF ₃ FH 1
HFFH 1 H CF ₃ FH 2
HFFH 2 H CF ₃ Cl H 0
H Cl Cl H 0 H CF ₃ Cl H 1
H Cl Cl H 1 H CF ₃ Cl H 2
H Cl Cl H 2 H CF ₃ Br H 0
H Br Br H 0 H CF ₃ Br H 1
H Br Br H 1 H CF ₃ Br H 2
H Br Br H 2 H CF ₃ IH 0
HIIH 0 H CF ₃ IH 1
HIIH 1 H CF ₃ IH 2
HIIH 2 H CF ₃ CN H 0
HF Cl H 0 H CF ₃ CN H 1
―――――――――――― H CF ₃ CN H 2
―――――――――――――

[Table 8]

Continuation of [Table 8] Continuation of [Table 8] ――――――――――――― ――――――――――――
Y1 Y2 Y3 Y4 n Y1 Y2 Y3 Y4 n
――――――――――――― ――――――――――――
HHHH 0 HIHH 1
HHHH 1 HIHH 2
HHHH 2 H Me HH 0
FHHH 0 H Me HH 1
FHHH 1 H Me HH 2
FHHH 2 H CF ₃ HH 0
Cl HHH 0 H CF ₃ HH 1
Cl HHH 1 H CF ₃ HH 2
Cl HHH 2 H CF ₂ CF ₃ HH 0
Br HHH 0 H CF ₂ CF ₃ HH 1
Br HHH 1 H CF ₂ CF ₃ HH 2
Br HHH 2 H CF(CF ₃ ) ₂ HH 0
IHHH 0 H CF(CF ₃ ) ₂ HH 1
IHHH 1 H CF(CF ₃ ) ₂ HH 2
IHHH 2 H SMe HH 0
Me HHH 0 H SMe HH 1
Me HHH 1 H SMe HH 2
Me HHH 2 H SOMe HH 0
CF ₃ HHH 0 H SOMe HH 1
CF ₃ HHH 1 H SOMe HH 2
CF ₃ HHH 2 H SO ₂ Me HH 0
HFHH 0 H SO ₂ Me HH 1
HFHH 1 H SO ₂ Me HH 2
HFHH 2 H OMe HH 0
H Cl HH 0 H OMe HH 1
H Cl HH 1 H OMe HH 2
H Cl HH 2 H OCF ₃ HH 0
H Br HH 0 H OCF ₃ HH 1
H Br HH 1 H OCF ₃ HH 2
H Br HH 2 H NO ₂ HH 0
HIHH 0 ――――――――――――
――――――――――――
Continuation of [Table 8] Continuation of [Table 8]――――――――――――――――――――――――――
Y1 Y2 Y3 Y4 n Y1 Y2 Y3 Y4 n
――――――――――――――――――――――――――
H NO ₂ HH 1 HHHI 2
H NO ₂ HH 2 HHH Me 0
H CN HH 0 HHH Me 1
H CN HH 1 HHH Me 2
H CN HH 2 HHH CF ₃ 0
HHFH 0 HHH CF ₃ 1
HHFH 1 HHH CF ₃ 2
HHFH 2 HHH CF ₂ CF ₃ 0
HH Cl H 0 HHH CF ₂ CF ₃ 1
HH Cl H 1 HHH CF ₂ CF ₃ 2
HH Cl H 2 HHH CF(CF ₃ ) ₂₀
HH Br H 0 HHH CF(CF ₃ ) ₂ 1
HH Br H 1 HHH CF(CF ₃ ) ₂ 2
HH Br H 2 HHH SMe 0
HHIH 0 HHH SMe 1
HHIH 1 HHH SMe 2
HHIH 2 HHH SOMe 0
HH Me H 0 HHH SOMe 1
HH Me H 1 HHH SOMe 2
HH Me H 2 HHH SO ₂ Me 0
HH CF ₃ H 0 HHH SO ₂ Me 1
HH CF ₃ H 1 HHH SO ₂ Me 2
HH CF ₃ H 2 HHH OMe 0
HH CF ₂ CF ₃ H 0 HHH OMe 1
HH CF ₂ CF ₃ H 1 HHH OMe 2
HH CF ₂ CF ₃ H 2 HHH OCF ₃ 0
HH CF(CF ₃ ) ₂ H 0 HHH OCF ₃ 1
HH CF(CF ₃ ) ₂ H 1 HHH OCF ₃ 2
HH CF(CF ₃ ) ₂ H 2 HHH NO ₂ 0
HH SMe H 0 HHH NO ₂ 1
HH SMe H 1 HHH NO ₂ 2
HH SMe H 2 HHH CN 0
HH SOMe H 0 HHH CN 1
HH SOMe H 1 HHH CN 2
HH SOMe H 2 HFHF 0
HH SO ₂ Me H 0 HFHF 1
HH SO ₂ Me H 1 HFHF 2
HH SO ₂ Me H 2 H Cl H Cl 0
HH OMe H 0 H Cl H Cl 1
HH OMe H 1 H Cl H Cl 2
HH OMe H 2 H Br H Br 0
HH OCF ₃ H 0 H Br H Br 1
HH OCF ₃ H 1 H Br H Br 2
HH OCF ₃ H 2 HIHI 0
HH NO ₂ H 0 HIHI 1
HH NO ₂ H 1 HIHI 2
HH NO ₂ H 2 HFH Cl 0
HH CN H 0 HFH Cl 1
HH CN H 1 HFH Cl 2
HH CN H 2 HFH Br 0
HHHF 0 HFH Br 1
HHHF 1 HFH Br 2
HHHF 2 HFHI 0
HHH Cl 0 HFHI 1
HHH Cl 1 HFHI 2
HHH Cl 2 H Cl HF 0
HHH Br 0 H Cl HF 1
HHH Br 1 H Cl HF 2
HHH Br 2 H Cl H Br 0
HHHI 0 H Cl H Br 1
HHHI 1 H Cl H Br 2
―――――――――――― ――――――――――――
Continuation of [Table 8] Continuation of [Table 8]――――――――――――――――――――――――――
Y1 Y2 Y3 Y4 n Y1 Y2 Y3 Y4 n
――――――――――――――――――――――――――
H Cl HI 0 HF Cl H 1
H Cl HI 1 HF Cl H 2
H Cl HI 2 HF Br H 0
H Br HF 0 HF Br H 1
H Br HF 1 HF Br H 2
H Br HF 2 HFIH 0
H Br H Cl 0 HFIH 1
H Br H Cl 1 HFIH 2
H Br H Cl 2 H Cl FH 0
H Br HI 0 H Cl FH 1
H Br HI 1 H Cl FH 2
H Br HI 2 H Cl Br H 0
HIHF 0 H Cl Br H 1
HIHF 1 H Cl Br H 2
HIHF 2 H Cl IH 0
HIH Cl 0 H Cl IH 1
HIH Cl 1 H Cl IH 2
HIH Cl 2 H Br FH 0
HIH Br 0 H Br FH 1
HIH Br 1 H Br FH 2
HIH Br 2 H Br Cl H 0
HFH CN 0 H Br Cl H 1
HFH CN 1 H Br Cl H 2
HFH CN 2 H Br IH 0
H Cl H CN 0 H Br IH 1
H Cl H CN 1 H Br IH 2
H Cl H CN 2 HIFH 0
H Br H CN 0 HIFH 1
H Br H CN 1 HIFH 2
H Br H CN 2 HI Cl H 0
HIH CN 0 HI Cl H 1
HIH CN 1 HI Cl H 2
HIH CN 2 HI Br H 0
――――――――――――――――――――――――――
Continuation of [Table 8] Continuation of [Table 8]――――――――――――――――――――――――――
Y1 Y2 Y3 Y4 n Y1 Y2 Y3 Y4 n
――――――――――――――――――――――――――
H CF ₃ HF 0 HI Br H 1
H CF ₃ HF 1 HI Br H 2
H CF ₃ HF 2 HF CN H 0
H CF ₃ H Cl 0 HF CN H 1
H CF ₃ H Cl 1 HF CN H 2
H CF ₃ H Cl 2 H Cl CN H 0
H CF ₃ H Br 0 H Cl CN H 1
H CF ₃ H Br 1 H Cl CN H 2
H CF ₃ H Br 2 H Br CN H 0
H CF ₃ HI 0 H Br CN H 1
H CF ₃ HI 1 H Br CN H 2
H CF ₃ HI 2 HI CN H 0
H CF ₃ H CN 0 HI CN H 1
H CF ₃ H CN 1 HI CN H 2
H CF ₃ H CN 2 H CF ₃ FH 0
HFFH 0 H CF ₃ FH 1
HFFH 1 H CF ₃ FH 2
HFFH 2 H CF ₃ Cl H 0
H Cl Cl H 0 H CF ₃ Cl H 1
H Cl Cl H 1 H CF ₃ Cl H 2
H Cl Cl H 2 H CF ₃ Br H 0
H Br Br H 0 H CF ₃ Br H 1
H Br Br H 1 H CF ₃ Br H 2
H Br Br H 2 H CF ₃ IH 0
HIIH 0 H CF ₃ IH 1
HIIH 1 H CF ₃ IH 2
HIIH 2 H CF ₃ CN H 0
HF Cl H 0 H CF ₃ CN H 1
―――――――――――― H CF ₃ CN H 2
―――――――――――――

[Table 9]

Continuation of [Table 9] Continuation of [Table 9] ――――――――――――― ――――――――――――
Y1 Y2 Y3 Y4 n Y1 Y2 Y3 Y4 n
――――――――――――― ――――――――――――
HHHH 0 HIHH 1
HHHH 1 HIHH 2
HHHH 2 H Me HH 0
FHHH 0 H Me HH 1
FHHH 1 H Me HH 2
FHHH 2 H CF ₃ HH 0
Cl HHH 0 H CF ₃ HH 1
Cl HHH 1 H CF ₃ HH 2
Cl HHH 2 H CF ₂ CF ₃ HH 0
Br HHH 0 H CF ₂ CF ₃ HH 1
Br HHH 1 H CF ₂ CF ₃ HH 2
Br HHH 2 H CF(CF ₃ ) ₂ HH 0
IHHH 0 H CF(CF ₃ ) ₂ HH 1
IHHH 1 H CF(CF ₃ ) ₂ HH 2
IHHH 2 H SMe HH 0
Me HHH 0 H SMe HH 1
Me HHH 1 H SMe HH 2
Me HHH 2 H SOMe HH 0
CF ₃ HHH 0 H SOMe HH 1
CF ₃ HHH 1 H SOMe HH 2
CF ₃ HHH 2 H SO ₂ Me HH 0
HFHH 0 H SO ₂ Me HH 1
HFHH 1 H SO ₂ Me HH 2
HFHH 2 H OMe HH 0
H Cl HH 0 H OMe HH 1
H Cl HH 1 H OMe HH 2
H Cl HH 2 H OCF ₃ HH 0
H Br HH 0 H OCF ₃ HH 1
H Br HH 1 H OCF ₃ HH 2
H Br HH 2 H NO ₂ HH 0
HIHH 0 ――――――――――――
――――――――――――
Continued from [Table 9] Continued from [Table 9]――――――――――――――――――――――――――
Y1 Y2 Y3 Y4 n Y1 Y2 Y3 Y4 n
――――――――――――――――――――――――――
H NO ₂ HH 1 HHHI 2
H NO ₂ HH 2 HHH Me 0
H CN HH 0 HHH Me 1
H CN HH 1 HHH Me 2
H CN HH 2 HHH CF ₃ 0
HHFH 0 HHH CF ₃ 1
HHFH 1 HHH CF ₃ 2
HHFH 2 HHH CF ₂ CF ₃ 0
HH Cl H 0 HHH CF ₂ CF ₃ 1
HH Cl H 1 HHH CF ₂ CF ₃ 2
HH Cl H 2 HHH CF(CF ₃ ) ₂₀
HH Br H 0 HHH CF(CF ₃ ) ₂ 1
HH Br H 1 HHH CF(CF ₃ ) ₂ 2
HH Br H 2 HHH SMe 0
HHIH 0 HHH SMe 1
HHIH 1 HHH SMe 2
HHIH 2 HHH SOMe 0
HH Me H 0 HHH SOMe 1
HH Me H 1 HHH SOMe 2
HH Me H 2 HHH SO ₂ Me 0
HH CF ₃ H 0 HHH SO ₂ Me 1
HH CF ₃ H 1 HHH SO ₂ Me 2
HH CF ₃ H 2 HHH OMe 0
HH CF ₂ CF ₃ H 0 HHH OMe 1
HH CF ₂ CF ₃ H 1 HHH OMe 2
HH CF ₂ CF ₃ H 2 HHH OCF ₃ 0
HH CF(CF ₃ ) ₂ H 0 HHH OCF ₃ 1
HH CF(CF ₃ ) ₂ H 1 HHH OCF ₃ 2
HH CF(CF ₃ ) ₂ H 2 HHH NO ₂ 0
HH SMe H 0 HHH NO ₂ 1
HH SMe H 1 HHH NO ₂ 2
HH SMe H 2 HHH CN 0
HH SOMe H 0 HHH CN 1
HH SOMe H 1 HHH CN 2
HH SOMe H 2 HFHF 0
HH SO ₂ Me H 0 HFHF 1
HH SO ₂ Me H 1 HFHF 2
HH SO ₂ Me H 2 H Cl H Cl 0
HH OMe H 0 H Cl H Cl 1
HH OMe H 1 H Cl H Cl 2
HH OMe H 2 H Br H Br 0
HH OCF ₃ H 0 H Br H Br 1
HH OCF ₃ H 1 H Br H Br 2
HH OCF ₃ H 2 HIHI 0
HH NO ₂ H 0 HIHI 1
HH NO ₂ H 1 HIHI 2
HH NO ₂ H 2 HFH Cl 0
HH CN H 0 HFH Cl 1
HH CN H 1 HFH Cl 2
HH CN H 2 HFH Br 0
HHHF 0 HFH Br 1
HHHF 1 HFH Br 2
HHHF 2 HFHI 0
HHH Cl 0 HFHI 1
HHH Cl 1 HFHI 2
HHH Cl 2 H Cl HF 0
HHH Br 0 H Cl HF 1
HHH Br 1 H Cl HF 2
HHH Br 2 H Cl H Br 0
HHHI 0 H Cl H Br 1
HHHI 1 H Cl H Br 2
―――――――――――― ――――――――――――
Continuation of [Table 9] Continuation of [Table 9]――――――――――――――――――――――――――
Y1 Y2 Y3 Y4 n Y1 Y2 Y3 Y4 n
――――――――――――――――――――――――――
H Cl HI 0 HF Cl H 1
H Cl HI 1 HF Cl H 2
H Cl HI 2 HF Br H 0
H Br HF 0 HF Br H 1
H Br HF 1 HF Br H 2
H Br HF 2 HFIH 0
H Br H Cl 0 HFIH 1
H Br H Cl 1 HFIH 2
H Br H Cl 2 H Cl FH 0
H Br HI 0 H Cl FH 1
H Br HI 1 H Cl FH 2
H Br HI 2 H Cl Br H 0
HIHF 0 H Cl Br H 1
HIHF 1 H Cl Br H 2
HIHF 2 H Cl IH 0
HIH Cl 0 H Cl IH 1
HIH Cl 1 H Cl IH 2
HIH Cl 2 H Br FH 0
HIH Br 0 H Br FH 1
HIH Br 1 H Br FH 2
HIH Br 2 H Br Cl H 0
HFH CN 0 H Br Cl H 1
HFH CN 1 H Br Cl H 2
HFH CN 2 H Br IH 0
H Cl H CN 0 H Br IH 1
H Cl H CN 1 H Br IH 2
H Cl H CN 2 HIFH 0
H Br H CN 0 HIFH 1
H Br H CN 1 HIFH 2
H Br H CN 2 HI Cl H 0
HIH CN 0 HI Cl H 1
HIH CN 1 HI Cl H 2
HIH CN 2 HI Br H 0
――――――――――――――――――――――――――
Continuation of [Table 9] Continuation of [Table 9]――――――――――――――――――――――――――
Y1 Y2 Y3 Y4 n Y1 Y2 Y3 Y4 n
――――――――――――――――――――――――――
H CF ₃ HF 0 HI Br H 1
H CF ₃ HF 1 HI Br H 2
H CF ₃ HF 2 HF CN H 0
H CF ₃ H Cl 0 HF CN H 1
H CF ₃ H Cl 1 HF CN H 2
H CF ₃ H Cl 2 H Cl CN H 0
H CF ₃ H Br 0 H Cl CN H 1
H CF ₃ H Br 1 H Cl CN H 2
H CF ₃ H Br 2 H Br CN H 0
H CF ₃ HI 0 H Br CN H 1
H CF ₃ HI 1 H Br CN H 2
H CF ₃ HI 2 HI CN H 0
H CF ₃ H CN 0 HI CN H 1
H CF ₃ H CN 1 HI CN H 2
H CF ₃ H CN 2 H CF ₃ FH 0
HFFH 0 H CF ₃ FH 1
HFFH 1 H CF ₃ FH 2
HFFH 2 H CF ₃ Cl H 0
H Cl Cl H 0 H CF ₃ Cl H 1
H Cl Cl H 1 H CF ₃ Cl H 2
H Cl Cl H 2 H CF ₃ Br H 0
H Br Br H 0 H CF ₃ Br H 1
H Br Br H 1 H CF ₃ Br H 2
H Br Br H 2 H CF ₃ IH 0
HIIH 0 H CF ₃ IH 1
HIIH 1 H CF ₃ IH 2
HIIH 2 H CF ₃ CN H 0
HF Cl H 0 H CF ₃ CN H 1
―――――――――――― H CF ₃ CN H 2
―――――――――――――
[Table 10]

Continuation of [Table 10] Continuation of [Table 10] ――――――――――――― ――――――――――――
Y1 Y2 Y3 Y4 n Y1 Y2 Y3 Y4 n
――――――――――――― ――――――――――――
HHHH 0 HIHH 1
HHHH 1 HIHH 2
HHHH 2 H Me HH 0
FHHH 0 H Me HH 1
FHHH 1 H Me HH 2
FHHH 2 H CF ₃ HH 0
Cl HHH 0 H CF ₃ HH 1
Cl HHH 1 H CF ₃ HH 2
Cl HHH 2 H CF ₂ CF ₃ HH 0
Br HHH 0 H CF ₂ CF ₃ HH 1
Br HHH 1 H CF ₂ CF ₃ HH 2
Br HHH 2 H CF(CF ₃ ) ₂ HH 0
IHHH 0 H CF(CF ₃ ) ₂ HH 1
IHHH 1 H CF(CF ₃ ) ₂ HH 2
IHHH 2 H SMe HH 0
Me HHH 0 H SMe HH 1
Me HHH 1 H SMe HH 2
Me HHH 2 H SOMe HH 0
CF ₃ HHH 0 H SOMe HH 1
CF ₃ HHH 1 H SOMe HH 2
CF ₃ HHH 2 H SO ₂ Me HH 0
HFHH 0 H SO ₂ Me HH 1
HFHH 1 H SO ₂ Me HH 2
HFHH 2 H OMe HH 0
H Cl HH 0 H OMe HH 1
H Cl HH 1 H OMe HH 2
H Cl HH 2 H OCF ₃ HH 0
H Br HH 0 H OCF ₃ HH 1
H Br HH 1 H OCF ₃ HH 2
H Br HH 2 H NO ₂ HH 0
HIHH 0 ――――――――――――
――――――――――――
Continuation of [Table 10] Continuation of [Table 10] ――――――――――――――――――――――――――
Y1 Y2 Y3 Y4 n Y1 Y2 Y3 Y4 n
――――――――――――――――――――――――――
H NO ₂ HH 1 HHHI 2
H NO ₂ HH 2 HHH Me 0
H CN HH 0 HHH Me 1
H CN HH 1 HHH Me 2
H CN HH 2 HHH CF ₃ 0
HHFH 0 HHH CF ₃ 1
HHFH 1 HHH CF ₃ 2
HHFH 2 HHH CF ₂ CF ₃ 0
HH Cl H 0 HHH CF ₂ CF ₃ 1
HH Cl H 1 HHH CF ₂ CF ₃ 2
HH Cl H 2 HHH CF(CF ₃ ) ₂₀
HH Br H 0 HHH CF(CF ₃ ) ₂ 1
HH Br H 1 HHH CF(CF ₃ ) ₂ 2
HH Br H 2 HHH SMe 0
HHIH 0 HHH SMe 1
HHIH 1 HHH SMe 2
HHIH 2 HHH SOMe 0
HH Me H 0 HHH SOMe 1
HH Me H 1 HHH SOMe 2
HH Me H 2 HHH SO ₂ Me 0
HH CF ₃ H 0 HHH SO ₂ Me 1
HH CF ₃ H 1 HHH SO ₂ Me 2
HH CF ₃ H 2 HHH OMe 0
HH CF ₂ CF ₃ H 0 HHH OMe 1
HH CF ₂ CF ₃ H 1 HHH OMe 2
HH CF ₂ CF ₃ H 2 HHH OCF ₃ 0
HH CF(CF ₃ ) ₂ H 0 HHH OCF ₃ 1
HH CF(CF ₃ ) ₂ H 1 HHH OCF ₃ 2
HH CF(CF ₃ ) ₂ H 2 HHH NO ₂ 0
HH SMe H 0 HHH NO ₂ 1
HH SMe H 1 HHH NO ₂ 2
HH SMe H 2 HHH CN 0
HH SOMe H 0 HHH CN 1
HH SOMe H 1 HHH CN 2
HH SOMe H 2 HFHF 0
HH SO ₂ Me H 0 HFHF 1
HH SO ₂ Me H 1 HFHF 2
HH SO ₂ Me H 2 H Cl H Cl 0
HH OMe H 0 H Cl H Cl 1
HH OMe H 1 H Cl H Cl 2
HH OMe H 2 H Br H Br 0
HH OCF ₃ H 0 H Br H Br 1
HH OCF ₃ H 1 H Br H Br 2
HH OCF ₃ H 2 HIHI 0
HH NO ₂ H 0 HIHI 1
HH NO ₂ H 1 HIHI 2
HH NO ₂ H 2 HFH Cl 0
HH CN H 0 HFH Cl 1
HH CN H 1 HFH Cl 2
HH CN H 2 HFH Br 0
HHHF 0 HFH Br 1
HHHF 1 HFH Br 2
HHHF 2 HFHI 0
HHH Cl 0 HFHI 1
HHH Cl 1 HFHI 2
HHH Cl 2 H Cl HF 0
HHH Br 0 H Cl HF 1
HHH Br 1 H Cl HF 2
HHH Br 2 H Cl H Br 0
HHHI 0 H Cl H Br 1
HHHI 1 H Cl H Br 2
―――――――――――― ――――――――――――
Continuation of [Table 10] Continuation of [Table 10] ――――――――――――――――――――――――――
Y1 Y2 Y3 Y4 n Y1 Y2 Y3 Y4 n
――――――――――――――――――――――――――
H Cl HI 0 HF Cl H 1
H Cl HI 1 HF Cl H 2
H Cl HI 2 HF Br H 0
H Br HF 0 HF Br H 1
H Br HF 1 HF Br H 2
H Br HF 2 HFIH 0
H Br H Cl 0 HFIH 1
H Br H Cl 1 HFIH 2
H Br H Cl 2 H Cl FH 0
H Br HI 0 H Cl FH 1
H Br HI 1 H Cl FH 2
H Br HI 2 H Cl Br H 0
HIHF 0 H Cl Br H 1
HIHF 1 H Cl Br H 2
HIHF 2 H Cl IH 0
HIH Cl 0 H Cl IH 1
HIH Cl 1 H Cl IH 2
HIH Cl 2 H Br FH 0
HIH Br 0 H Br FH 1
HIH Br 1 H Br FH 2
HIH Br 2 H Br Cl H 0
HFH CN 0 H Br Cl H 1
HFH CN 1 H Br Cl H 2
HFH CN 2 H Br IH 0
H Cl H CN 0 H Br IH 1
H Cl H CN 1 H Br IH 2
H Cl H CN 2 HIFH 0
H Br H CN 0 HIFH 1
H Br H CN 1 HIFH 2
H Br H CN 2 HI Cl H 0
HIH CN 0 HI Cl H 1
HIH CN 1 HI Cl H 2
HIH CN 2 HI Br H 0
――――――――――――――――――――――――――
Continuation of [Table 10] Continuation of [Table 10] ――――――――――――――――――――――――――
Y1 Y2 Y3 Y4 n Y1 Y2 Y3 Y4 n
――――――――――――――――――――――――――
H CF ₃ HF 0 HI Br H 1
H CF ₃ HF 1 HI Br H 2
H CF ₃ HF 2 HF CN H 0
H CF ₃ H Cl 0 HF CN H 1
H CF ₃ H Cl 1 HF CN H 2
H CF ₃ H Cl 2 H Cl CN H 0
H CF ₃ H Br 0 H Cl CN H 1
H CF ₃ H Br 1 H Cl CN H 2
H CF ₃ H Br 2 H Br CN H 0
H CF ₃ HI 0 H Br CN H 1
H CF ₃ HI 1 H Br CN H 2
H CF ₃ HI 2 HI CN H 0
H CF ₃ H CN 0 HI CN H 1
H CF ₃ H CN 1 HI CN H 2
H CF ₃ H CN 2 H CF ₃ FH 0
HFFH 0 H CF ₃ FH 1
HFFH 1 H CF ₃ FH 2
HFFH 2 H CF ₃ Cl H 0
H Cl Cl H 0 H CF ₃ Cl H 1
H Cl Cl H 1 H CF ₃ Cl H 2
H Cl Cl H 2 H CF ₃ Br H 0
H Br Br H 0 H CF ₃ Br H 1
H Br Br H 1 H CF ₃ Br H 2
H Br Br H 2 H CF ₃ IH 0
HIIH 0 H CF ₃ IH 1
HIIH 1 H CF ₃ IH 2
HIIH 2 H CF ₃ CN H 0
HF Cl H 0 H CF ₃ CN H 1
―――――――――――― H CF ₃ CN H 2
―――――――――――――
[Table 11]

Continuation of [Table 11] Continuation of [Table 11] ――――――――――――― ――――――――――――
Y1 Y2 Y3 Y4 n Y1 Y2 Y3 Y4 n
――――――――――――― ――――――――――――
HHHH 0 HIHH 1
HHHH 1 HIHH 2
HHHH 2 H Me HH 0
FHHH 0 H Me HH 1
FHHH 1 H Me HH 2
FHHH 2 H CF ₃ HH 0
Cl HHH 0 H CF ₃ HH 1
Cl HHH 1 H CF ₃ HH 2
Cl HHH 2 H CF ₂ CF ₃ HH 0
Br HHH 0 H CF ₂ CF ₃ HH 1
Br HHH 1 H CF ₂ CF ₃ HH 2
Br HHH 2 H CF(CF ₃ ) ₂ HH 0
IHHH 0 H CF(CF ₃ ) ₂ HH 1
IHHH 1 H CF(CF ₃ ) ₂ HH 2
IHHH 2 H SMe HH 0
Me HHH 0 H SMe HH 1
Me HHH 1 H SMe HH 2
Me HHH 2 H SOMe HH 0
CF ₃ HHH 0 H SOMe HH 1
CF ₃ HHH 1 H SOMe HH 2
CF ₃ HHH 2 H SO ₂ Me HH 0
HFHH 0 H SO ₂ Me HH 1
HFHH 1 H SO ₂ Me HH 2
HFHH 2 H OMe HH 0
H Cl HH 0 H OMe HH 1
H Cl HH 1 H OMe HH 2
H Cl HH 2 H OCF ₃ HH 0
H Br HH 0 H OCF ₃ HH 1
H Br HH 1 H OCF ₃ HH 2
H Br HH 2 H NO ₂ HH 0
HIHH 0 ――――――――――――
――――――――――――
Continuation of [Table 11] Continuation of [Table 11]――――――――――――――――――――――――――
Y1 Y2 Y3 Y4 n Y1 Y2 Y3 Y4 n
――――――――――――――――――――――――――
H NO ₂ HH 1 HHHI 2
H NO ₂ HH 2 HHH Me 0
H CN HH 0 HHH Me 1
H CN HH 1 HHH Me 2
H CN HH 2 HHH CF ₃ 0
HHFH 0 HHH CF ₃ 1
HHFH 1 HHH CF ₃ 2
HHFH 2 HHH CF ₂ CF ₃ 0
HH Cl H 0 HHH CF ₂ CF ₃ 1
HH Cl H 1 HHH CF ₂ CF ₃ 2
HH Cl H 2 HHH CF(CF ₃ ) ₂₀
HH Br H 0 HHH CF(CF ₃ ) ₂ 1
HH Br H 1 HHH CF(CF ₃ ) ₂ 2
HH Br H 2 HHH SMe 0
HHIH 0 HHH SMe 1
HHIH 1 HHH SMe 2
HHIH 2 HHH SOMe 0
HH Me H 0 HHH SOMe 1
HH Me H 1 HHH SOMe 2
HH Me H 2 HHH SO ₂ Me 0
HH CF ₃ H 0 HHH SO ₂ Me 1
HH CF ₃ H 1 HHH SO ₂ Me 2
HH CF ₃ H 2 HHH OMe 0
HH CF ₂ CF ₃ H 0 HHH OMe 1
HH CF ₂ CF ₃ H 1 HHH OMe 2
HH CF ₂ CF ₃ H 2 HHH OCF ₃ 0
HH CF(CF ₃ ) ₂ H 0 HHH OCF ₃ 1
HH CF(CF ₃ ) ₂ H 1 HHH OCF ₃ 2
HH CF(CF ₃ ) ₂ H 2 HHH NO ₂ 0
HH SMe H 0 HHH NO ₂ 1
HH SMe H 1 HHH NO ₂ 2
HH SMe H 2 HHH CN 0
HH SOMe H 0 HHH CN 1
HH SOMe H 1 HHH CN 2
HH SOMe H 2 HFHF 0
HH SO ₂ Me H 0 HFHF 1
HH SO ₂ Me H 1 HFHF 2
HH SO ₂ Me H 2 H Cl H Cl 0
HH OMe H 0 H Cl H Cl 1
HH OMe H 1 H Cl H Cl 2
HH OMe H 2 H Br H Br 0
HH OCF ₃ H 0 H Br H Br 1
HH OCF ₃ H 1 H Br H Br 2
HH OCF ₃ H 2 HIHI 0
HH NO ₂ H 0 HIHI 1
HH NO ₂ H 1 HIHI 2
HH NO ₂ H 2 HFH Cl 0
HH CN H 0 HFH Cl 1
HH CN H 1 HFH Cl 2
HH CN H 2 HFH Br 0
HHHF 0 HFH Br 1
HHHF 1 HFH Br 2
HHHF 2 HFHI 0
HHH Cl 0 HFHI 1
HHH Cl 1 HFHI 2
HHH Cl 2 H Cl HF 0
HHH Br 0 H Cl HF 1
HHH Br 1 H Cl HF 2
HHH Br 2 H Cl H Br 0
HHHI 0 H Cl H Br 1
HHHI 1 H Cl H Br 2
―――――――――――― ――――――――――――
Continuation of [Table 11] Continuation of [Table 11]――――――――――――――――――――――――――
Y1 Y2 Y3 Y4 n Y1 Y2 Y3 Y4 n
――――――――――――――――――――――――――
H Cl HI 0 HF Cl H 1
H Cl HI 1 HF Cl H 2
H Cl HI 2 HF Br H 0
H Br HF 0 HF Br H 1
H Br HF 1 HF Br H 2
H Br HF 2 HFIH 0
H Br H Cl 0 HFIH 1
H Br H Cl 1 HFIH 2
H Br H Cl 2 H Cl FH 0
H Br HI 0 H Cl FH 1
H Br HI 1 H Cl FH 2
H Br HI 2 H Cl Br H 0
HIHF 0 H Cl Br H 1
HIHF 1 H Cl Br H 2
HIHF 2 H Cl IH 0
HIH Cl 0 H Cl IH 1
HIH Cl 1 H Cl IH 2
HIH Cl 2 H Br FH 0
HIH Br 0 H Br FH 1
HIH Br 1 H Br FH 2
HIH Br 2 H Br Cl H 0
HFH CN 0 H Br Cl H 1
HFH CN 1 H Br Cl H 2
HFH CN 2 H Br IH 0
H Cl H CN 0 H Br IH 1
H Cl H CN 1 H Br IH 2
H Cl H CN 2 HIFH 0
H Br H CN 0 HIFH 1
H Br H CN 1 HIFH 2
H Br H CN 2 HI Cl H 0
HIH CN 0 HI Cl H 1
HIH CN 1 HI Cl H 2
HIH CN 2 HI Br H 0
――――――――――――――――――――――――――
Continuation of [Table 11] Continuation of [Table 11]――――――――――――――――――――――――――
Y1 Y2 Y3 Y4 n Y1 Y2 Y3 Y4 n
――――――――――――――――――――――――――
H CF ₃ HF 0 HI Br H 1
H CF ₃ HF 1 HI Br H 2
H CF ₃ HF 2 HF CN H 0
H CF ₃ H Cl 0 HF CN H 1
H CF ₃ H Cl 1 HF CN H 2
H CF ₃ H Cl 2 H Cl CN H 0
H CF ₃ H Br 0 H Cl CN H 1
H CF ₃ H Br 1 H Cl CN H 2
H CF ₃ H Br 2 H Br CN H 0
H CF ₃ HI 0 H Br CN H 1
H CF ₃ HI 1 H Br CN H 2
H CF ₃ HI 2 HI CN H 0
H CF ₃ H CN 0 HI CN H 1
H CF ₃ H CN 1 HI CN H 2
H CF ₃ H CN 2 H CF ₃ FH 0
HFFH 0 H CF ₃ FH 1
HFFH 1 H CF ₃ FH 2
HFFH 2 H CF ₃ Cl H 0
H Cl Cl H 0 H CF ₃ Cl H 1
H Cl Cl H 1 H CF ₃ Cl H 2
H Cl Cl H 2 H CF ₃ Br H 0
H Br Br H 0 H CF ₃ Br H 1
H Br Br H 1 H CF ₃ Br H 2
H Br Br H 2 H CF ₃ IH 0
HIIH 0 H CF ₃ IH 1
HIIH 1 H CF ₃ IH 2
HIIH 2 H CF ₃ CN H 0
HF Cl H 0 H CF ₃ CN H 1
―――――――――――― H CF ₃ CN H 2
―――――――――――――
[Table 12]

Continuation of [Table 12] Continuation of [Table 12] ――――――――――――― ――――――――――――
Y1 Y2 Y3 Y4 n Y1 Y2 Y3 Y4 n
――――――――――――― ――――――――――――
HHHH 0 HIHH 1
HHHH 1 HIHH 2
HHHH 2 H Me HH 0
FHHH 0 H Me HH 1
FHHH 1 H Me HH 2
FHHH 2 H CF ₃ HH 0
Cl HHH 0 H CF ₃ HH 1
Cl HHH 1 H CF ₃ HH 2
Cl HHH 2 H CF ₂ CF ₃ HH 0
Br HHH 0 H CF ₂ CF ₃ HH 1
Br HHH 1 H CF ₂ CF ₃ HH 2
Br HHH 2 H CF(CF ₃ ) ₂ HH 0
IHHH 0 H CF(CF ₃ ) ₂ HH 1
IHHH 1 H CF(CF ₃ ) ₂ HH 2
IHHH 2 H SMe HH 0
Me HHH 0 H SMe HH 1
Me HHH 1 H SMe HH 2
Me HHH 2 H SOMe HH 0
CF ₃ HHH 0 H SOMe HH 1
CF ₃ HHH 1 H SOMe HH 2
CF ₃ HHH 2 H SO ₂ Me HH 0
HFHH 0 H SO ₂ Me HH 1
HFHH 1 H SO ₂ Me HH 2
HFHH 2 H OMe HH 0
H Cl HH 0 H OMe HH 1
H Cl HH 1 H OMe HH 2
H Cl HH 2 H OCF ₃ HH 0
H Br HH 0 H OCF ₃ HH 1
H Br HH 1 H OCF ₃ HH 2
H Br HH 2 H NO ₂ HH 0
HIHH 0 ――――――――――――
――――――――――――
Continuation of [Table 12] Continuation of [Table 12]――――――――――――――――――――――――――
Y1 Y2 Y3 Y4 n Y1 Y2 Y3 Y4 n
――――――――――――――――――――――――――
H NO ₂ HH 1 HHHI 2
H NO ₂ HH 2 HHH Me 0
H CN HH 0 HHH Me 1
H CN HH 1 HHH Me 2
H CN HH 2 HHH CF ₃ 0
HHFH 0 HHH CF ₃ 1
HHFH 1 HHH CF ₃ 2
HHFH 2 HHH CF ₂ CF ₃ 0
HH Cl H 0 HHH CF ₂ CF ₃ 1
HH Cl H 1 HHH CF ₂ CF ₃ 2
HH Cl H 2 HHH CF(CF ₃ ) ₂₀
HH Br H 0 HHH CF(CF ₃ ) ₂ 1
HH Br H 1 HHH CF(CF ₃ ) ₂ 2
HH Br H 2 HHH SMe 0
HHIH 0 HHH SMe 1
HHIH 1 HHH SMe 2
HHIH 2 HHH SOMe 0
HH Me H 0 HHH SOMe 1
HH Me H 1 HHH SOMe 2
HH Me H 2 HHH SO ₂ Me 0
HH CF ₃ H 0 HHH SO ₂ Me 1
HH CF ₃ H 1 HHH SO ₂ Me 2
HH CF ₃ H 2 HHH OMe 0
HH CF ₂ CF ₃ H 0 HHH OMe 1
HH CF ₂ CF ₃ H 1 HHH OMe 2
HH CF ₂ CF ₃ H 2 HHH OCF ₃ 0
HH CF(CF ₃ ) ₂ H 0 HHH OCF ₃ 1
HH CF(CF ₃ ) ₂ H 1 HHH OCF ₃ 2
HH CF(CF ₃ ) ₂ H 2 HHH NO ₂ 0
HH SMe H 0 HHH NO ₂ 1
HH SMe H 1 HHH NO ₂ 2
HH SMe H 2 HHH CN 0
HH SOMe H 0 HHH CN 1
HH SOMe H 1 HHH CN 2
HH SOMe H 2 HFHF 0
HH SO ₂ Me H 0 HFHF 1
HH SO ₂ Me H 1 HFHF 2
HH SO ₂ Me H 2 H Cl H Cl 0
HH OMe H 0 H Cl H Cl 1
HH OMe H 1 H Cl H Cl 2
HH OMe H 2 H Br H Br 0
HH OCF ₃ H 0 H Br H Br 1
HH OCF ₃ H 1 H Br H Br 2
HH OCF ₃ H 2 HIHI 0
HH NO ₂ H 0 HIHI 1
HH NO ₂ H 1 HIHI 2
HH NO ₂ H 2 HFH Cl 0
HH CN H 0 HFH Cl 1
HH CN H 1 HFH Cl 2
HH CN H 2 HFH Br 0
HHHF 0 HFH Br 1
HHHF 1 HFH Br 2
HHHF 2 HFHI 0
HHH Cl 0 HFHI 1
HHH Cl 1 HFHI 2
HHH Cl 2 H Cl HF 0
HHH Br 0 H Cl HF 1
HHH Br 1 H Cl HF 2
HHH Br 2 H Cl H Br 0
HHHI 0 H Cl H Br 1
HHHI 1 H Cl H Br 2
―――――――――――― ――――――――――――
Continuation of [Table 12] Continuation of [Table 12]――――――――――――――――――――――――――
Y1 Y2 Y3 Y4 n Y1 Y2 Y3 Y4 n
――――――――――――――――――――――――――
H Cl HI 0 HF Cl H 1
H Cl HI 1 HF Cl H 2
H Cl HI 2 HF Br H 0
H Br HF 0 HF Br H 1
H Br HF 1 HF Br H 2
H Br HF 2 HFIH 0
H Br H Cl 0 HFIH 1
H Br H Cl 1 HFIH 2
H Br H Cl 2 H Cl FH 0
H Br HI 0 H Cl FH 1
H Br HI 1 H Cl FH 2
H Br HI 2 H Cl Br H 0
HIHF 0 H Cl Br H 1
HIHF 1 H Cl Br H 2
HIHF 2 H Cl IH 0
HIH Cl 0 H Cl IH 1
HIH Cl 1 H Cl IH 2
HIH Cl 2 H Br FH 0
HIH Br 0 H Br FH 1
HIH Br 1 H Br FH 2
HIH Br 2 H Br Cl H 0
HFH CN 0 H Br Cl H 1
HFH CN 1 H Br Cl H 2
HFH CN 2 H Br IH 0
H Cl H CN 0 H Br IH 1
H Cl H CN 1 H Br IH 2
H Cl H CN 2 HIFH 0
H Br H CN 0 HIFH 1
H Br H CN 1 HIFH 2
H Br H CN 2 HI Cl H 0
HIH CN 0 HI Cl H 1
HIH CN 1 HI Cl H 2
HIH CN 2 HI Br H 0
――――――――――――――――――――――――――
Continuation of [Table 12] Continuation of [Table 12]――――――――――――――――――――――――――
Y1 Y2 Y3 Y4 n Y1 Y2 Y3 Y4 n
――――――――――――――――――――――――――
H CF ₃ HF 0 HI Br H 1
H CF ₃ HF 1 HI Br H 2
H CF ₃ HF 2 HF CN H 0
H CF ₃ H Cl 0 HF CN H 1
H CF ₃ H Cl 1 HF CN H 2
H CF ₃ H Cl 2 H Cl CN H 0
H CF ₃ H Br 0 H Cl CN H 1
H CF ₃ H Br 1 H Cl CN H 2
H CF ₃ H Br 2 H Br CN H 0
H CF ₃ HI 0 H Br CN H 1
H CF ₃ HI 1 H Br CN H 2
H CF ₃ HI 2 HI CN H 0
H CF ₃ H CN 0 HI CN H 1
H CF ₃ H CN 1 HI CN H 2
H CF ₃ H CN 2 H CF ₃ FH 0
HFFH 0 H CF ₃ FH 1
HFFH 1 H CF ₃ FH 2
HFFH 2 H CF ₃ Cl H 0
H Cl Cl H 0 H CF ₃ Cl H 1
H Cl Cl H 1 H CF ₃ Cl H 2
H Cl Cl H 2 H CF ₃ Br H 0
H Br Br H 0 H CF ₃ Br H 1
H Br Br H 1 H CF ₃ Br H 2
H Br Br H 2 H CF ₃ IH 0
HIIH 0 H CF ₃ IH 1
HIIH 1 H CF ₃ IH 2
HIIH 2 H CF ₃ CN H 0
HF Cl H 0 H CF ₃ CN H 1
―――――――――――― H CF ₃ CN H 2
―――――――――――――
[Table 13]

Continuation of [Table 13] Continuation of [Table 13] ――――――――――――― ――――――――――――
Y1 Y2 Y3 Y4 n Y1 Y2 Y3 Y4 n
――――――――――――― ――――――――――――
HHHH 0 HIHH 1
HHHH 1 HIHH 2
HHHH 2 H Me HH 0
FHHH 0 H Me HH 1
FHHH 1 H Me HH 2
FHHH 2 H CF ₃ HH 0
Cl HHH 0 H CF ₃ HH 1
Cl HHH 1 H CF ₃ HH 2
Cl HHH 2 H CF ₂ CF ₃ HH 0
Br HHH 0 H CF ₂ CF ₃ HH 1
Br HHH 1 H CF ₂ CF ₃ HH 2
Br HHH 2 H CF(CF ₃ ) ₂ HH 0
IHHH 0 H CF(CF ₃ ) ₂ HH 1
IHHH 1 H CF(CF ₃ ) ₂ HH 2
IHHH 2 H SMe HH 0
Me HHH 0 H SMe HH 1
Me HHH 1 H SMe HH 2
Me HHH 2 H SOMe HH 0
CF ₃ HHH 0 H SOMe HH 1
CF ₃ HHH 1 H SOMe HH 2
CF ₃ HHH 2 H SO ₂ Me HH 0
HFHH 0 H SO ₂ Me HH 1
HFHH 1 H SO ₂ Me HH 2
HFHH 2 H OMe HH 0
H Cl HH 0 H OMe HH 1
H Cl HH 1 H OMe HH 2
H Cl HH 2 H OCF ₃ HH 0
H Br HH 0 H OCF ₃ HH 1
H Br HH 1 H OCF ₃ HH 2
H Br HH 2 H NO ₂ HH 0
HIHH 0 ――――――――――――
――――――――――――
Continuation of [Table 13] Continuation of [Table 13]――――――――――――――――――――――――――
Y1 Y2 Y3 Y4 n Y1 Y2 Y3 Y4 n
――――――――――――――――――――――――――
H NO ₂ HH 1 HHHI 2
H NO ₂ HH 2 HHH Me 0
H CN HH 0 HHH Me 1
H CN HH 1 HHH Me 2
H CN HH 2 HHH CF ₃ 0
HHFH 0 HHH CF ₃ 1
HHFH 1 HHH CF ₃ 2
HHFH 2 HHH CF ₂ CF ₃ 0
HH Cl H 0 HHH CF ₂ CF ₃ 1
HH Cl H 1 HHH CF ₂ CF ₃ 2
HH Cl H 2 HHH CF(CF ₃ ) ₂₀
HH Br H 0 HHH CF(CF ₃ ) ₂ 1
HH Br H 1 HHH CF(CF ₃ ) ₂ 2
HH Br H 2 HHH SMe 0
HHIH 0 HHH SMe 1
HHIH 1 HHH SMe 2
HHIH 2 HHH SOMe 0
HH Me H 0 HHH SOMe 1
HH Me H 1 HHH SOMe 2
HH Me H 2 HHH SO ₂ Me 0
HH CF ₃ H 0 HHH SO ₂ Me 1
HH CF ₃ H 1 HHH SO ₂ Me 2
HH CF ₃ H 2 HHH OMe 0
HH CF ₂ CF ₃ H 0 HHH OMe 1
HH CF ₂ CF ₃ H 1 HHH OMe 2
HH CF ₂ CF ₃ H 2 HHH OCF ₃ 0
HH CF(CF ₃ ) ₂ H 0 HHH OCF ₃ 1
HH CF(CF ₃ ) ₂ H 1 HHH OCF ₃ 2
HH CF(CF ₃ ) ₂ H 2 HHH NO ₂ 0
HH SMe H 0 HHH NO ₂ 1
HH SMe H 1 HHH NO ₂ 2
HH SMe H 2 HHH CN 0
HH SOMe H 0 HHH CN 1
HH SOMe H 1 HHH CN 2
HH SOMe H 2 HFHF 0
HH SO ₂ Me H 0 HFHF 1
HH SO ₂ Me H 1 HFHF 2
HH SO ₂ Me H 2 H Cl H Cl 0
HH OMe H 0 H Cl H Cl 1
HH OMe H 1 H Cl H Cl 2
HH OMe H 2 H Br H Br 0
HH OCF ₃ H 0 H Br H Br 1
HH OCF ₃ H 1 H Br H Br 2
HH OCF ₃ H 2 HIHI 0
HH NO ₂ H 0 HIHI 1
HH NO ₂ H 1 HIHI 2
HH NO ₂ H 2 HFH Cl 0
HH CN H 0 HFH Cl 1
HH CN H 1 HFH Cl 2
HH CN H 2 HFH Br 0
HHHF 0 HFH Br 1
HHHF 1 HFH Br 2
HHHF 2 HFHI 0
HHH Cl 0 HFHI 1
HHH Cl 1 HFHI 2
HHH Cl 2 H Cl HF 0
HHH Br 0 H Cl HF 1
HHH Br 1 H Cl HF 2
HHH Br 2 H Cl H Br 0
HHHI 0 H Cl H Br 1
HHHI 1 H Cl H Br 2
―――――――――――― ――――――――――――
Continuation of [Table 13] Continuation of [Table 13]――――――――――――――――――――――――――
Y1 Y2 Y3 Y4 n Y1 Y2 Y3 Y4 n
――――――――――――――――――――――――――
H Cl HI 0 HF Cl H 1
H Cl HI 1 HF Cl H 2
H Cl HI 2 HF Br H 0
H Br HF 0 HF Br H 1
H Br HF 1 HF Br H 2
H Br HF 2 HFIH 0
H Br H Cl 0 HFIH 1
H Br H Cl 1 HFIH 2
H Br H Cl 2 H Cl FH 0
H Br HI 0 H Cl FH 1
H Br HI 1 H Cl FH 2
H Br HI 2 H Cl Br H 0
HIHF 0 H Cl Br H 1
HIHF 1 H Cl Br H 2
HIHF 2 H Cl IH 0
HIH Cl 0 H Cl IH 1
HIH Cl 1 H Cl IH 2
HIH Cl 2 H Br FH 0
HIH Br 0 H Br FH 1
HIH Br 1 H Br FH 2
HIH Br 2 H Br Cl H 0
HFH CN 0 H Br Cl H 1
HFH CN 1 H Br Cl H 2
HFH CN 2 H Br IH 0
H Cl H CN 0 H Br IH 1
H Cl H CN 1 H Br IH 2
H Cl H CN 2 HIFH 0
H Br H CN 0 HIFH 1
H Br H CN 1 HIFH 2
H Br H CN 2 HI Cl H 0
HIH CN 0 HI Cl H 1
HIH CN 1 HI Cl H 2
HIH CN 2 HI Br H 0
――――――――――――――――――――――――――
Continuation of [Table 13] Continuation of [Table 13]――――――――――――――――――――――――――
Y1 Y2 Y3 Y4 n Y1 Y2 Y3 Y4 n
――――――――――――――――――――――――――
H CF ₃ HF 0 HI Br H 1
H CF ₃ HF 1 HI Br H 2
H CF ₃ HF 2 HF CN H 0
H CF ₃ H Cl 0 HF CN H 1
H CF ₃ H Cl 1 HF CN H 2
H CF ₃ H Cl 2 H Cl CN H 0
H CF ₃ H Br 0 H Cl CN H 1
H CF ₃ H Br 1 H Cl CN H 2
H CF ₃ H Br 2 H Br CN H 0
H CF ₃ HI 0 H Br CN H 1
H CF ₃ HI 1 H Br CN H 2
H CF ₃ HI 2 HI CN H 0
H CF ₃ H CN 0 HI CN H 1
H CF ₃ H CN 1 HI CN H 2
H CF ₃ H CN 2 H CF ₃ FH 0
HFFH 0 H CF ₃ FH 1
HFFH 1 H CF ₃ FH 2
HFFH 2 H CF ₃ Cl H 0
H Cl Cl H 0 H CF ₃ Cl H 1
H Cl Cl H 1 H CF ₃ Cl H 2
H Cl Cl H 2 H CF ₃ Br H 0
H Br Br H 0 H CF ₃ Br H 1
H Br Br H 1 H CF ₃ Br H 2
H Br Br H 2 H CF ₃ IH 0
HIIH 0 H CF ₃ IH 1
HIIH 1 H CF ₃ IH 2
HIIH 2 H CF ₃ CN H 0
HF Cl H 0 H CF ₃ CN H 1
―――――――――――― H CF ₃ CN H 2
―――――――――――――
The pest control agent in the present invention refers to the field of agriculture and horticulture or the field of livestock and sanitation (internal parasites/ectoparasites against mammals or birds as livestock and pets, household and commercial hygiene pests/unpleasant pests). Etc. means a pest control agent for harmful arthropods. Further, the pesticide in the present invention means an insecticide/miticide, nematicide, herbicide, fungicide and the like in the field of agriculture and horticulture.

Specific examples of insects, mites, crustaceans, molluscs and nematodes that can be controlled using the compound of the present invention include, for example, the following organisms, but the present invention is not limited thereto. It is not something that will be done.

Tea squirrels (Adoxophyes honmai), apple squirrels (Adoxophyes orana faciata), apple squirrels (Archips breviplicanus), weeping squirrels (Archips fuscocupreanus), pear squirrels (Grapholita molesta), tea squirrels (Homona) Leguminivora glycinivorella), Mamehimesamushiga moth (Matsumuraeses phaseoli), Tobihamaki (Pandemis heparana), Nashibiga (Bucculatrix pyriorella Pyorga moth (Lyonetia clairella) orlyon moth (Lyonetia clella), Lyonetia clella (Pyrrhenia vulgaris) ringoniella), citrus fruit moth (Phyllocnistis citrella), green stalk moth (Acrolepiopsis sapporensis), wild yam moth (Acrolepiopsis suzukiella), diamondback moth (Plutella xylostella), red moss worm (Stathmopoda masinissa), potato mosquito slab (Homo serrata) sasakii), codling moth (Cydla pomonella), nigga moth (Chilo suppressalis), cobno moth (Cnaphalocrocis medinalis), peach monocod moth (Conogethes punctiferalis), cotton helicopter moth (Diaphania indica), white-toothed moth ella ella iga (Eti) Glyphodes pyloalis), Himaula moth (Hellula undalis), Awanomega (Ostrinia furnacalis), Azukinomega (Ostrinia scapulalis), Yo Ropian corn borer (Ostrinia nubilalis), Shibattoga (Parapediasia teterrella), Ichimonjiseri (Parnara guttata), Pieris brassicae (Pieris rapae crucivora), White-billed butterfly (Pieris rapae crucivora) (Euproctis pseudoconspersa), gypsy moth (Lymantria dispar), black-spotted moth (Orgyia thyellina), American white-hit (Hyphantria cunea), stilt (Lemyra imparilis), Akebikonoha (Adris tyrannus), nakajiro-shia una (Ara eda), Aomeda educa ), Kaburayaga (Agrotis segetum), Tamanaginuwaba (Autographa nigrisigna), Mitsumonkinuwaba (Ctenoplusia agnata), Helicoverpa armigera, Tobacco moth (Helicoverpa assulta), Cotton ball worm (Helicoverpa zea), Helicoverpa zea (Helicoverpa zea), Tobacco bud , Japanese armyworm (Mamestra brassicae), armyworm (Mythimna separata), bivalve moth (Naranga aenescens), Southern army worm (Spodoptera eridania), white armyworm (Spodoptera exigua), fall army worm (Spodoptera frewera), Spodoptera frugiera (Spodoptera litura), swordfish (Spodoptera depravata), nettle alba (Trichoplusia ni), grapeberry moss (Endopiza viteana), tomato horn worm (Manduca quinquemaculata), tobacco horn worm (Manduca sexta) ) Etc. Lepidoptera insects.

Thrips thrips (Frankliniella intonsa), orange thrips (Frankliniella occidentalis), black thrips (Heliothrips haemorrhoidalis), tea tree palm thrips (Scirtothrips dorsalis) Insects of the order Lepidoptera.

Spotted beetle (Dolycoris baccarum), sea turtle (Eurydema rugosum), stag beetle (Eysarcoris aeneus), beetle worm (Eysarcoris lewis), white-headed stink bug (Eysarcoris halus) (Eysarcoris ventralis) , Blue-breasted stink bug (Nezara antennata), Southern green stink bug (Nezara viridula), Black-headed stink bug (Piezodorus hybneri), Green grass stink bug (Plautia crossota), Rice black stink bug (Scotinophora lurida), Helicopter warbler Stink bugs (Leptocorisa chinensis), Japanese beetle (Riptortus clavatus), Red beetle Helicopter beetle (Rhopalus msculatus), Kanbane beetle (Cavelerius saccharivorus), Black beetle (Togo hemipdercus), Red beetle (Togo hemipdercus) (Stephanitis pyrioides), Black-backed turtle (Halticus insularis), Polished plant bug (Lygus lineolaris), Nagomikasutemu (Stenodema sibiricum), Red-crowned turtle (Stenotus rubrovittatus), Rice-spotted midge turtle (Trigonotylus cael), Trigonotylus cael Leafhopper leafhopper (Arboridia apicalis), leafhopper leafhopper (Balclutha saltuella), leafhopper leafhopper (Epiacanthus stramineus), potato leafhopper (Empoasca fabae), leafhopper leafhopper (Empoasca nipponica), tea leafhopper leafhopper (Empoasca nipponica) Green leafhopper (Empoa asca sakaii), Green leafhopper (Macroste) les striifrons), green leafhoppers (Nephotettix cinctinceps), cotton-free hoppers (Psuedatomoscelis seriatus), rockhoppers (Laodelphax striatella), brown planthoppers (Nilaparvata luia), white-bellied planthoppers (Nilaparvata lua) Whitefly (Aleurocanthus spiniferus), Silverleaf whitefly (Bemisia argentifolii), Tobacco whitefly (Bemisia tabaci), Orange whitefly (Dialeurodes citri), Whitefly whitefly (Trialeurodes vaporariorum), Grape aphid (Viteus phitas aphis, Viteus vitifolis) Aphid (Aphis spiraecola), green peach aphid (Myzus persicae), rice aphid (Toxoptera aurantii), large scale insect (Drosicha corpulenta), moss scale insect (Icerya purchasi), stag beetle (Phenacoccus) citri), Fujia stag beetle (Planococcus kuraunhiae), stag beetle (Pseudococcus comstocki), horn beetle (Ceroplastes ceriferus), ruby weevil (Ceroplastes rubens), red scale bug (Aonidiella aurantii perm, persian) theae), Pseudaonidia paeoniae, Pseudaonidia paeoniae, Pseudaulacaspis pentagona, Pseudaulacaspis prunicola, Unaspis Hemiptera insects such as euonymi, Unaspis yanonensis, and bed bug, Cimex lectularius.

Lobster buoy (Anomala cuprea), Japanese beetle (Anomala rufocuprea), Core beetle (Gametis jucunda), Long beetle (Heptophylla picea), Japanese beetle (Popillia japonica), Colorado potato beetle (Lepinotarsa decemlineta), Maltese beetle (Lepinotarsa decemlineata) White-faced beetle (Melanotus tamsuyensis), tobacco beetle (Lasioderma serricorne), white-bellied beetle (Epuraea domina), green kidney beetle (Epilachna varivestis), black-spotted beetle (Epilachna vigintioctopunctata), white-breasted beetle (Epilachna vigintioctopunctata) Tribolium castaneum), stag beetle (Anoplophora malasiaca), pine wood beetle (Monochamus alternatus), yellow beetle (Psacothea hilaris), grape tiger beetle (Xylotrechus feline ham) (Chaetocnema concinna), Southern corn root worm (Diabrotica undecimpunctata), Western corn root worm (Diabrotica virgifera), Northern corn root worm (Diabrotica barberi), Rice duck beetle (Oulema oryzae), Phyllotreta striolat (Phyllotreta striolat) eggplant angusticollis), peach weevil (Rhynchites heros), aphid weevil (Cylas formicarius), weevil (Anthonomus grandis), rice weevil (Echinocnemus squameus), weevil (Euscepes postfascia) tus), alfalfa weevil (Hypera postica), rice weevil (Lissohoptrus oryzophilus), stag beetle (Otiorhynchus sulcatus), granary weevil (Sitophilus atusophus, ovaphenus), weevil (Sitophilus vius ophaeum) Coleoptera insects such as arigata beetle (Paederus fuscipes).

Soybean leaf flies (Asphondylia yushimai), water fly (Sitodiplosis mosellana), fruit fly (Bactrocera cucurbitae), orange fruit fly (Bactrocera dorsalis), fruit fly (Ceratitis capitata), rice leaf fly (Ceratitis capitata), rice leaf fly (Ceratitis capitata) Leaf fly (Agromyza oryzae), leaf fly (Chromatomyia horticola), leaf fly (Liriomyza bryoniae), green leaf fly (Liriomyza chinensis), tomato leaf fly (Liriomyza sativae), bean leaf fly (Liriomyza sativae), Liriomyza trifolii, Liriomyza trifolii (Pegomya cunicularia), apple maggot (Rhagoletis pomonella), hessian fry (Mayetiola destructor), house fly (Musca domestica), horn fly (Stomoxys calcitrans), sheep horn fly (Melophagus ovinus), bull fly (Hypoderma erba line) (Oestrus ovis), tsetse flies (Glossina palpalis, Glossina morsitans), yellow-tailed squirrels (Prosimulium yezoensis), cow flies (Tabanus trigonus), giant fly flies (Telmatoscopus albipunctatus pis aca pisces) ), Aedes albopicutus, and Anopheles hyracanus sinesis.

Yellow-bellied bee (Apethymus kuri), black-bellied wasp (Athalia rosae), black-spotted wasp (Arge pagana), pine bee (Neodiprion sertifer), black-bee bee (Dryocosmus kuriphilus), junta ants (Eciton burchelli, Eciton ochmit) Hymenoptera insects such as mandarina), bulldog ant (Myrmecia spp.), fire ant (Solenopsis spp.), and pharaoh ant (Monomorium pharaonis).

Orthoptera insects such as Emma cricket (Teleogryllus emma), kerula (Gryllotalpa orientalis), locust grasshopper (Locusta migratoria), coba neago (Oxya yezoensis), and mackerel locust (Schistocerca gregaria).

Viscous insects such as Onychiurus folsomi, Onychiurus sibiricus, and Bourletiella hortensis.

Insect insects such as black cockroaches (Periplaneta fuliginosa), Japanese cockroaches (Periplaneta japonica), and German cockroaches (Blattella germanica).

Termite insects such as house termites (Coptotermes formosanus), mountain termites (Reticulitermes speratus), and white termites (Odontotermes formosanus).

Flea species such as cat fleas (Ctenocephalidae felis), dog fleas (Ctenocephalides canis), chicken fleas (Echidnophaga gallinacea), human fleas (Pulex irritans), and cheops fleas (Xenopsylla cheopis).

Halioptera insects such as chicken white lice (Menacanthus stramineus) and bovine lice (Bovicola bovis).

Lice insects such as bovine lice (Haematopinus eurysternus), porcelain lice (Haematopinus suis), bull lice (Linognathus vituli), and bedbug lice (Solenopotes capillatus).

Dust mites such as cyclamen dust mite (Phytonemus pallidus), tea dust mite (Polyphagotarsonemus latus), and mite dust mite (Tarsonemus bilobatus).

Red-spotted mites such as Chinese mite (Penthaleus erythrocephalus) and wheat mite (Penthaleus major).

Rice spider mites (Oligonychus shinkajii), citrus spider mites (Panonychus citri), mulberry spider mites (Panonychus mori), apple spider mites (Panonychus ulmi), kanzawa mites (Tetranychus kanzawai), spider mites (Tetranychus urticae), etc.

Tea rust mite (Acaphylla theavagrans), tulip rust mite (Aceria tulipae), tomato rust mite (Aculops lycopersici), mandarin rust mite (Aculops pelekassi), apple rust mite (Aculus schlechtenoptali), mite rust mite (Eriophyes platrast) ) Etc.

Tick mites such as robined mite (Rhizoglyphus robini), diamondback moth (Tyrophagus putrescentiae), and spinach mite tick (Tyrophagus similis).

Bee mites such as honeybee mite (Varroa jacobsoni).

Boophilus microplus, Rhipicephalus sanguineus, Haemaphysalis longicornis, Haemophysalis flava, Haemaphysalis campanulata, Ixodes ovatus, Ixodes ovatus, Ixodes ovatus Amblyomma spp.) and ticks such as Dermacentor spp.

Mesostigmata mites such as red mite (Dermanyssus gallinae), house mite Tropical rat mite (Ornithonyssus bacoti), and northern fowl mite (Ornithonyssus sylviarum).

Timber ticks such as dog ticks (Cheyletiella yasguri) and cat ticks (Cheyletiella blakei).

Demodex mites such as Demodex canis and Demodex cati.

Dust mites such as sheep mite (Psoroptes ovis).

Helicoidal mites such as Sarcoptes scabiei, cat-to-white mite (Notoedres cati), and chicken mite (Knemidocoptes spp.).

Crustaceans such as the pill bug (Armadillidium vulgare).

Gastropods such as Spodoptera canalicula (Pomacea canaliculata), African snail (Achatina fulica), slug (Meghimatium bilineatum), tea slug (Limax Valentiana), Uskawamai (Acusta despecta sieboldiana), and Missimai maimai (Euhadra peliomphala).

Southern sage nematode (Prathylenchus coffeae), northern sedge nematode (Prathylenchus penetrans), walnut sedge nematode (Prathylenchus vulnus), potato cyst nematode (Globodera rostochiensis), soybean cyst nematode (Globodera rostochien) Nematodes such as root-knot nematodes (Meloidogyne incognita), rice garlic nematodes (Aphelenchoides besseyi), and pine wood nematodes (Bursaphelenchus xylophilus).

Flies or Haematobia irritans, flies or Tabanus spp. , Sand flies or Stomoxys calcitrans, Gnats or Simulium spp. , Mekrabab or Chrysops spp. , Licefly or Melophagus ovinus, and Tsetse fly or Glossina spp. Adult flies such as.

Sheep fly (Oestrus ovis and Cuterebra spp.), blowfly or Phaenicia spp. , Drosophila melanogaster or Cochliomyia hominivorax, bullfly or Hypoderma spp. Flies of horses, fleeceworm and Gastrophilus.

Culex spp. , Anopheles spp. And Aedes spp. Mosquito etc.

The internal parasites of livestock, poultry, pets and the like that can be controlled using the compound of the present invention specifically include, for example, the following internal parasites, but the present invention is not limited thereto. Not something.

Haemonchus, Trichostrongylus, Ostertagia, Nematodirus, Cooperia, Ascaris, Bunostomum, Esphagostomum Genus (Oesophagostomum), genus Chabertia (genus Chabertia), genus Trichuris (genus Trichuris), genus Storongylus (genus Tricononema), genus Ditricioocaulus (genus Dictyocaulus), genus Capillaria, genus Heterakis ), Toxocara (Toxocara), Ascaridia (Ascaridia), Oxyuris (Oxyuris), Ankylostoma (Ancylostoma), Uncynaria (Uncinaria), Toxascaris (Toxascaris), Parascaris (Parascaris) and other nematodes ..

Nematodes of the family Filariidae, such as the genus Wuchereria, the genus Brugia, the genus Onchoceca, the genus Dirofilaria, and the genus Loa, Loa.

Dracunculidae nematodes, such as the genus Deacunculus.

Tapeworm (Dipylidium caninum), tapeworm (Taenia taeniaeformis), tapeworm (Taenia solium), tapeworm (Taenia saginata), tapeworm (Hymenolepis diminuta), tapeworm Beneden (Moniezia benedeni), Streptococci such as Diphyllobothrium latum, Manson cephalopoda, Diphyllobothrium erinacei, Echinococcus granulosus, and Echinococcus multilocularis.

Liver fluke (Fasciola hepatica, F. gigantica), Paragonimus westermanii, Paragonimus westermanii, hypertrophic fluke (Fasciolopsic bruski), pancreas fluke (Eurytrema pancreaticum, E.coelomaticum), liver fluke (Clonorchis sinensis), Schistosoma japonicum japonicum), Schistosoma haematobium, and Schistosoma mansoni.

Eimeria tenella, Eimeria acervulina, Eimeria brunetti, Eimeria maxima, Eimeria necatrix, Eimeria bovis, Eimeria bovis Eimeria spp., such as Eberia ovinoidalis.

Trypanosomsa cruzi, Leishmania spp., Plasmodium spp., Babesia sp., Trichomonadidae spp., Histomonas spp., Giardia (Giardia spp.), Toxoplasma spp., Entamoeba histolytica, Theileria spp.

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

That is, the compound of the present invention, Mucocidae (Collembola), Thysanoptera (Broccidae), Orthoptera (Locustidea), Termites, Thysanoptera (Thysanoptera), Hemiptera (Hemiptera and leafhoppers) Eyes), Lepidoptera (Lepidoptera), Coleoptera (Coleoptera), Hymenoptera (Hymenoptera), Diptera (Flies), Isoptera (fleas), Insects such as lice, and mites Pests belonging to gastropods, nematodes, etc. can be effectively controlled at low concentrations.

On the other hand, the compound of the present invention has very little adverse effect on mammals, fish, crustaceans, and beneficial insects (bees, bees, and other useful insects and honeybees, wasps, mosquitoes, stink bugs, natural mites such as acarid mites), and is extremely useful. It has various features.

In using the compound of the present invention, it is usually mixed with a suitable solid carrier or liquid carrier, and further, if desired, a surfactant, a penetrating agent, a spreading agent, a thickening agent, an antifreezing agent, a binder, anticaking agent. Soluble concentrate, emulsion (emulsifiable concentrate), wettable powder, water soluble powder, granules Water dispersible granule, water soluble granule, suspension concentrate, concentrated emulsion, suspoemulsion, microemulsion, dustable Powder), granules, tablets, emulsifiable gels, etc. Further, from the viewpoint of labor saving and safety improvement, the formulation of any of the above dosage forms can be provided by enclosing it in a water-soluble package such as a water-soluble capsule or a bag of a water-soluble film.

As the solid carrier, for example, quartz, calcite, sepiolite, dolomite, chalk, kaolinite, pyrophyllite, sericite, halosite, metahalosite, kibushi clay, frog eye clay, porcelain stone, sikhlite, Natural mineral substances such as allophane, shirasu, kira, talc, bentonite, activated clay, acid clay, pumice, attapulgite, zeolite, diatomaceous earth; calcined clay, perlite, silas balloon, vermiculite, attapalgas clay, calcined diatomaceous earth Quality baked products; Inorganic salts such as magnesium carbonate, calcium carbonate, sodium carbonate, sodium hydrogen carbonate, ammonium sulfate, sodium sulfate, magnesium sulfate, diammonium hydrogen phosphate, ammonium dihydrogen phosphate, potassium chloride; glucose, fructose, sucrose , Saccharides such as lactose; polysaccharides such as starch, powdered cellulose, dextrin; organic substances such as urea, urea derivatives, benzoic acid, salts of benzoic acid; wood flour, cork flour, corn cobs, walnut shells, tobacco stems, etc. Plants; fly ash, white carbon (for example, hydrous synthetic silica, anhydrous synthetic silica, hydrous synthetic silicate, etc.), fertilizer;

Examples of the liquid carrier include aromatic hydrocarbons such as xylene, alkyl (C ₉ or C ₁₀ etc.) benzene, phenylxylylethane, alkyl (C ₁ or C ₃ etc.) naphthalene; machine oil, normal paraffin, isoparaffin. , Aliphatic hydrocarbons such as naphthene; mixtures of aromatic hydrocarbons and aliphatic hydrocarbons such as kerosene; alcohols such as ethanol, isopropanol, cyclohexanol, phenoxyethanol, benzyl alcohol; ethylene glycol, propylene glycol, diethylene glycol, hexylene Polyhydric alcohols such as glycol, polyethylene glycol, polypropylene glycol; propyl cellosolve, butyl cellosolve, phenyl cellosolve, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, propylene glycol monophenyl ether, etc. Ethers; ketones such as acetophenone, cyclohexanone, γ-butyrolactone; esters of fatty acid methyl esters, succinic acid dialkyl esters, glutamic acid dialkyl esters, adipic acid dialkyl esters, phthalic acid dialkyl esters, etc.; N-alkyl (C1, C8 or C12 etc.) Acid amides such as pyrrolidone; oils and fats such as soybean oil, linseed oil, rapeseed oil, coconut oil, cottonseed oil, castor oil; dimethyl sulfoxide, water; and the like.

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

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 and polyoxyethylene polyoxypropylene block copolymer. Oxyethylene fatty acid (mono or di) ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, castor oil ethylene oxide adduct, acetylene glycol, acetylene alcohol, acetylene glycol ethylene oxide adduct, acetylene alcohol ethylene oxide adduct, Nonionic surfactants such as alkyl glycosides; alkyl sulfate ester salts, alkylbenzene sulfonates, lignin sulfonates, alkyl sulfosuccinates, naphthalene sulfonates, alkylnaphthalene sulfonates, salts of formalin condensates of naphthalene sulfonates , Salt of formalin condensate of alkylnaphthalene sulfonic acid, polyoxyethylene alkyl ether sulfuric acid or phosphoric acid ester salt, polyoxyethylene (mono or di) alkyl phenyl ether sulfuric acid or phosphoric acid ester salt, polyoxyethylene (mono, di or tri) Anionic surfactants such as styryl phenyl ether sulfuric acid or phosphoric acid ester salts, polycarboxylic acid salts (for example, polyacrylic acid salts, polymaleic acid salts, copolymers of maleic acid and olefins), polystyrene sulfonic acid salts, etc.; alkyl Examples thereof include cationic surfactants such as amine salts and alkyl quaternary ammonium salts; amphoteric surfactants such as amino acid type and betaine type surfactants; silicone type surfactants and fluorine type surfactants.

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

The application dose of the compound of the present invention varies depending on the application scene, application time, application method, cultivated crop, etc., but normally, the amount of the active ingredient is preferably about 0.005 to 50 kg per hectare (ha). ..

On the other hand, when the compound of the present invention is used for controlling external or internal parasites of mammals and birds as domestic animals and pets, an effective amount of the compound of the present invention is orally administered together with a pharmaceutical additive; injection (muscle Parenteral administration such as intradermal, subcutaneous, intravenous, intraperitoneal, etc.; transdermal administration such as dipping, spraying, bathing, washing, pouring-on and spotting-on, dusting; Nasal administration; and the like. The compounds of the present invention can also be administered by shaped articles using strips, plates, bands, collars, ear marks, limb bands, marking devices and the like.

Upon administration, the compound of the present invention can be made into any dosage form suitable for the administration route.

When using the compound of the present invention to control ectoparasites or endoparasites, the preferable dose of the compound of the present invention represented by formula (1), which is an active ingredient, is the kind of the target parasite to be controlled, the subject to be administered. The amount is usually 0.01 to 100 mg/kg, preferably 0.01 to 50 mg/kg, based on the weight of the subject animal to be administered, although it depends on the species of the animal or the administration method. In particular, the dose to dogs may vary depending on the type or age of the target dog or the ectoparasite to be controlled, but is usually 1 to 5000 mg/kg per 1 kg live weight of the target dog. It is preferably 1 to 100 mg/kg.

When ectoparasites or endoparasites are exterminated by administration of the compound of the present invention, the administration interval depends on the type of the target parasite to be controlled, the species of the target animal to be administered, the administration method, etc., but usually, It can be arbitrarily set within the range of every day to once a year. It is preferably once a week to once every 6 months, more preferably daily (24 hours), monthly, once a month, once every two months or once every three months.

When the compound of the present invention is used for controlling ectoparasites in dogs, the compound of the present invention is orally administered to dogs at a timing of, for example, 30 minutes before the start of feeding or 120 minutes after the end of feeding. It can be mentioned. The term “30 minutes before the start of the diet and 120 minutes after the end of the diet” as used herein is based on the act of eating the feed given to the dog for the purpose of nutrition intake. For example, when the dog's diet time is 20 minutes, the prescribed time is 170 minutes in total, from 30 minutes before the start of the meal to 120 minutes after the end of the diet, based on the eating behavior. It also includes the case where the diet is interrupted once during the diet, the compound of the present invention is orally administered, and then the diet is resumed. In the present specification, the term “food” means the act of eating food by an animal.

In general, the number of times a dog eats per day varies depending on the breed, age, and habit, but normally, dogs younger than 6 months of age 3-4 times a day, dogs aged 6 months to less than 1 year 2 to 3 times a day, Adult dogs aged 1 to 5 years old are said to be twice a day, and old dogs aged 6 years or older are aged 2 to 3 times a day. In the present invention, the term “feed” means an eating action for the purpose of ingesting nutrition, and does not include so-called dog training or feeding for the purpose of training.

As the arbitrary dosage forms to be prepared, solid preparations such as powders, granules, wettable powders, pellets, tablets, large pills, capsules, molded products containing the active compound; injectable solutions, oral solutions, skin Liquid preparations such as liquids to be used above or in body cavities; Solution preparations such as dropping (Pour-on), spot-on, flowable, emulsions; semisolid preparations such as ointments and gels ; And the like.

The dosage form of the compound of the present invention for oral administration includes, for example, tablets (Tablets), solid dosage forms (Chewables), capsules (Capsules), pills (Pills), large pills (Boluses), and granules (Granules). ), solid preparations such as powders; semi-solid preparations such as pastes and gels; liquid preparations such as Drinks; and the like.

As a dosage form for transdermal administration, for example, solid preparations such as powders (Powders); creams (Cream), ointments (Salve and Ointment), pastes (Pastes), gels (Gels) And the like; liquid preparations such as sprays (Spray), aerosols (Aerosols), solutions (Solutions and Emulsions), suspensions (Suspensions), lotions (Lotions), and the like.

Further, the dosage form for administration by injection includes, for example, liquid preparations such as solutions (Solutions and Emulsions) and suspensions (Suspensions), and the dosage form for intranasal administration includes, for example, , Liquid preparations such as aerosols (Aerosols) and the like. In addition, as a dosage form when spraying treatment to an animal rearing environment such as a barn, for example, solid preparations such as wettable powders, dusts, granules and the like; emulsions (Emulsions) , Liquid preparations such as flowable agents (Suspension concentrates); and the like.

The formulation used for the parasite control agent of the present invention is not limited to these dosage forms.

The solid preparation may be orally administered as it is, or may be diluted with water and used for percutaneous administration, spray treatment in an animal breeding environment such as a barn, etc.

The solid preparation used for oral administration includes a compound represented by the formula (1) or a salt thereof, one or more excipients and binders suitable for oral administration, and, if necessary, a lubricant. It can be prepared by mixing with a physiologically acceptable additive such as an agent, a disintegrant, a dye or a pigment, and molding into a desired shape.

Examples of the excipient and the binder include sugars or sugar derivatives such as lactose, sucrose, mannitol, and sorbitol; corn starch, wheat starch, rice starch, potato starch and other starches; methyl cellulose, carboxymethyl cellulose, hydroxyethyl cellulose, hydroxy. Cellulose or cellulose derivatives such as propylcellulose and hydroxypropylmethylcellulose; proteins or protein derivatives such as zein and gelatin; synthetic polymer compounds such as honey, gum arabic paste, polyvinyl alcohol and polyvinylpyrrolidone; and the like.

Examples of the lubricant include magnesium stearate and the like, and examples of the disintegrator include cellulose, agar, alginic acid, crosslinked polyvinylpyrrolidinone, carbonate and the like.

Furthermore, among solid preparations used for oral administration, particularly in the case of solid preparations such as chewable agents, additives that impart the taste, texture, and flavor preferred by the animal to be administered are also used. The carriers and additives used in the solid preparations of the control composition are not limited to these.

Liquid preparations may be administered percutaneously or by injection, or may be mixed with feed and administered orally, diluted with water for percutaneous administration, and applied by spraying to animal rearing environments such as barns. You can

Injectable solutions can be administered intravenously, intramuscularly and subcutaneously. Injectable solutions can be prepared by dissolving the active compound in a suitable solvent and, if necessary, adding additives such as solubilizers, acids, bases, buffer salts, antioxidants and protectants.

Suitable solvents include water, ethanol, butanol, benzyl alcohol, glycerin, propylene glycol, polyethylene glycol, N-methylpyrrolidone and mixtures thereof, physiologically acceptable vegetable oils, synthetic oils suitable for injection and the like.

Examples of the solubilizer include polyvinylpyrrolidone, polyoxyethylated castor oil, polyoxyethylated sorbitan ester, and the like.

Examples of the protective agent include benzyl alcohol, trichlorobutanol, p-hydroxybenzoic acid ester, n-butanol and the like.

The oral liquid preparation can be administered directly or after dilution. It can be prepared in the same manner as the injectable solution.

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

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

Pour-on and spot-on agents can be dropped or sprayed on confined areas of the skin, whereby the active compound is immersed in the skin and has a systemic effect. it can.

Drops and lozenges can be prepared by dissolving, suspending, or emulsifying the active ingredient in a suitable skin-compatible solvent or solvent mixture. If necessary, an auxiliary agent such as a surfactant, a colorant, an absorption promoting substance, an antioxidant, a light stabilizer and an adhesive may be added.

Suitable solvents include water, alkanols, glycols, polyethylene glycols, polypropylene glycols, glycerin, benzyl alcohol, phenylethanol, phenoxyethanol, ethyl acetate, butyl acetate, benzyl benzoate, dipropylene glycol monomethyl ether, diethylene glycol monobutyl ether, acetone, Methyl ethyl ketone, aromatic and/or aliphatic hydrocarbons, vegetable or synthetic oils, DMF (N,N-dimethylformamide), liquid paraffin, light liquid paraffin, silicone, dimethylacetamide, N-methylpyrrolidone or 2,2-dimethyl- 4-oxy-methylene-1,3-dioxolane is mentioned.

Examples of the absorption enhancer include DMSO (dimethyl sulfoxide), isopropyl myristate, dipropylene glycol pelargonate, silicone oil, aliphatic ester, triglyceride or fatty alcohol.

Antioxidants include sulfites, metabisulfites, ascorbic acid, butylhydroxytoluene, butylhydroxyanisole or tocopherols.

The emulsion can be administered orally, transdermally or as an injection. Emulsions are prepared by dissolving the active ingredient in a hydrophobic phase or a hydrophilic phase, and further by adding a suitable emulsifier, if necessary, a coloring agent, an absorption promoting substance, a protective agent, an antioxidant, a light-shielding agent, a thickening substance. It can be prepared by homogenizing with a solvent of another phase together with an auxiliary agent such as.

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

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

As the emulsifier, non-ionic interfaces such as polyoxyethylated castor oil, polyoxyethylated sorbitan monoolefinate, sorbitan monostearate, glyceryl monostearate, polyoxyethyl stearate, alkylphenol polyglycol ether, etc. Active agents; amphoteric surfactants such as N-lauryl-β-iminodipropionate disodium and lecithin; anions such as sodium lauryl sulfate, fatty alcohol sulfate ethers, monoethanolamine salts of mono/dialkyl polyglycol orthophosphate And the like; cationic surfactants such as cetyltrimethylammonium chloride; and the like.

Other auxiliary agents include carboxymethyl cellulose, methyl cellulose, polyacrylate, alginate, gelatin, gum arabic, polyvinylpyrrolidone, polyvinyl alcohol, methyl vinyl ether, a copolymer of maleic anhydride, polyethylene glycol, wax, colloidal silica and the like. To be

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

Next, examples of formulation of the preparation when the compound of the present invention is used are shown. However, the compounding examples of the present invention are not limited to these. In the following formulation examples, "part" means part by mass.

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

〔emulsion〕
Compound of the present invention 0.1 to 30 parts Liquid carrier 45 to 95 parts Surfactant 4.9 to 15 parts Others 0 to 10 parts Other examples include spreading agents and decomposition inhibitors.

(Suspension agent)
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 Examples of other materials 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 Examples of other materials include, for example, binders and decomposition inhibitors.

[Liquid formulation]
Compound of the present invention 0.01 to 70 parts Liquid carrier 20 to 99.99 parts Others 0 to 10 parts Examples of other materials include, for example, 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 Examples of other materials include, for example, binders and decomposition inhibitors.

[Dust]
The compound of the present invention 0.01 to 30 parts Solid carrier 65 to 99.99 parts Others 0 to 5 parts Examples of the others include an anti-drift agent and an anti-decomposition agent.

Next, formulation examples using the compound of the present invention as an active ingredient will be shown more specifically, but the present invention is not limited thereto.

In the following formulation examples, "part" means part by mass.

[Formulation Example 1] Wettable powder of the present compound No. 1-1-001a 20 parts Pyrophyllite 74 parts Sorpol 5039 4 parts (trade name, mixture of nonionic surfactant and anionic surfactant: manufactured by Toho Chemical Industry Co., Ltd.).
Carplex #80D 2 parts (trade name, synthetic hydrous silicic acid: manufactured by Shionogi & Co.).
The above is uniformly mixed and pulverized to obtain a wettable powder.

[Formulation Example 2] Emulsion Compound No. of the present invention 1-1-001a 5 parts xylene 75 parts N-methylpyrrolidone 15 parts Sorpol 2680 5 parts (trade name, mixture of nonionic surfactant and anionic surfactant: manufactured by Toho Chemical Industry Co., Ltd.).
The above is uniformly mixed to obtain an emulsion.

[Formulation Example 3] Suspension agent Compound No. of the present invention 1-1-001a 25 parts Aglycol S-710 10 parts (trade name, nonionic surfactant: manufactured by Kao Corporation).
Lunox 1000C 0.5 part (trade name, anionic surfactant: manufactured by Toho Chemical Industry Co., Ltd.).
Xanthan gum 0.2 parts Water 64.3 parts After uniformly mixing the above, wet pulverize to obtain a suspension.

[Formulation Example 4] Granule wettable powder Compound of the present invention No. 1-1-001a 75 parts Hitenol NE-15 5 parts (trade name, anionic surfactant: manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.).
Vanilex N 10 parts (trade name, anionic surfactant: manufactured by Nippon Paper Industries Co., Ltd.).
Carplex #80D 10 parts (trade name, synthetic hydrous silicic acid: manufactured by Shionogi & Co.).
After uniformly mixing and pulverizing the above, a small amount of water is added, and the mixture is stirred and mixed, granulated by an extrusion granulator, and dried to obtain a granule wettable powder.

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

[Formulation Example 6] Powdered compound of the present invention No. 1-1-001a 3 parts Carplex #80D 0.5 part (trade name, synthetic hydrous silicic acid: manufactured by Shionogi & Co., Ltd.).
Kaolinite 95 parts Diisopropyl phosphate 1.5 parts The above are uniformly mixed and pulverized to give a powder.

At the time of use, the above-mentioned preparation is diluted 1 to 10000 times with water or directly sprayed without dilution.

[Formulation Example 7] Wettable powder preparation Compound No. 7 of the present invention 1-1-001a 25 parts Sodium diisobutylnaphthalenesulfonate 1 part Calcium n-dodecylbenzenesulfonate 10 parts Alkylaryl polyglycol ether 12 parts Sodium salt of naphthalenesulfonic acid formalin condensate 3 parts Emulsion type silicone 1 part Silicon dioxide 3 parts Kaolin 45 parts [Formulation example 8] Water-soluble thickener preparation Compound of the present invention No. 1-1-001a 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] Liquid formulation for spraying Compound of the present invention No. 1-1-001a 2 parts Dimethyl sulfoxide 10 parts 2-propanol 35 parts Acetone 53 parts [Formulation Example 10] Liquid preparation for transdermal administration Compound of the present invention No. 1-1-001a 5 parts Hexylene glycol 50 parts Isopropanol 45 parts [Formulation Example 11] Liquid preparation for transdermal administration Compound of the present invention No. 1-1-001a 5 parts Propylene glycol monomethyl ether 50 parts Dipropylene glycol 45 parts [Formulation Example 12] Liquid preparation for transdermal administration (drop) The present compound No. 1-1-001a 2 parts Light liquid paraffin 98 parts [Formulation Example 13] Liquid preparation for transdermal administration (dripping) Compound No. 1 of the present invention 1-1-001a 2 parts Light liquid paraffin 58 parts Olive oil 30 parts ODO-H 9 parts Shin-Etsu Silicone 1 part When the compound of the present invention is used as a pesticide, other types may be used at the time of formulation or spraying, if necessary. The herbicides, various insecticides, acaricides, nematicides, fungicides, plant growth regulators, synergists, fertilizers, soil conditioners and the like may be mixed and applied.

In particular, when mixed with other pesticides or plant hormones, it can be expected to reduce the amount of the applied drug, reduce the cost, expand the insecticidal spectrum by the synergistic action of the mixed drugs, and have a higher pest control effect. At this time, it is possible to combine a plurality of known pesticides at the same time.

Examples of the types of pesticides used in combination with the compound of the present invention include compounds described in The Pesticide Manual, 15th edition, 2009. Specific examples of the common names are as follows, but the general names are not limited thereto.

Fungicide: acibenzolar-S-methyl, acylaminobenzamide, acypetacs, aldimorph, amethoctrazine, aminopyrifen, amisulbrom, Ambam, ampropyfos, anilazine, anazazine, azaconazole, azithiram, azoxystrobin, barium polysulfide, benalaxyl, benalaxyl-M (Benalaxyl-M), benodanil, benomyl, benomyl, benquinox, bentaluron, benthiavalicarb-isopropyl, benthiazole, benzamacril, benzamacril, Benzamorf, benzovindiflupyr, bethoxazine, binapacryl, biphenyl, bitertanol, blasticidin-S, blasticidin-S, bixafen, Bordeaux mixture, boscalid, bromuconazole, bupirimate, buthiobate, lime-sulfur mixture, calcium polysulfide, calcium polysulfide, captafol , Captan, carpropamid, carbamorph, carbendazim, carboxin, carvone, cheshunt mixtur e), chinomethionat, chlobenthiazone, chloraniformethane, chloranil, chlorfenazol, chloroneb, chloropicrin, chlorothalonil. , Chlorquinox, chlozolinate, climbazole, clotrimazole, copper acetate, basic copper carbonate, cupric hydroxide copper hydroxide), copper naphthalene (copper naphthenate), copper oleate (copper oleate), copper oxychloride (copper oxychloride), copper sulfate (copper sulfate), basic copper sulfate (copper sulfate, basic), copper zinc chromate ( copper zinc chromate, cufraneb, coumoxystrobin, cuprobam, cyprofam, cyazofamid, cyclafuramid, cycloheximide, cyflufenamide, cyflufenamid, cymoxanil, cymoxanil, Cypendazole, cyproconazol, cyprodinil, cyprofuram, dazomet, debacarb, decafentin, dehydroacetic acid, diclo Benchazox (dichlobentiazox), dichlofluanid (dichlofluanid), dichlone (dichlone), dichlorophen (dichlorophen), diclozoline (dichlozoline), diclobutrazol (diclobutrazol), di Such as diclocymet, diclomedine, dichloran.

Disinfectants (continued): diethofencarb, difenoconazole, diflumetorim, dimethirimol, dimethomorph, dimoxystrobin, dimoxystrobin, diniconazole, diniconazole, diniconazole. M), dinobuton, dinocap, dinocap-4, dinocap-6, dinocapton, dinocton, dinosulfon, dinoterbon, diphenylamine ), dipymetitrone, dipyrithione, ditalimfos, dithianon, dodemorph-acetate, dodine, drazoxolone, edefenophos, edifenphos, edifenphos, edifenphos, edifenphos. , Enoxastrobin, epoxiconazole, etaconazole, ethaboxam, etem, ethirimol, ethoxyquin, ethdidiazole, famoxadone, Fenarimol, fenbuconazole, fenamidone, fenaminosulf, fenaminestrobin, fenapanil, fendazosulam, fenfuram, fenhexamide fenhexamid), fenitropan (fenitropan), phenoxanil (fenoxanil), fenpiclonil (fenpiclonil), fenpicoxamide (fenpicoxamid), fenpropidin (fenpropidin), Fenpyrazamine, fenpropimorph, fentin, fentin, ferbam, ferimzone, fluazinam, fludioxonil, fluphenoxystrobin, flufenoxystrobin, fluindapyr, fluindapyr, Flumetover, flumorph, fluopicolide, fluopyram, fluoroimide, fluotrimazole, fluoxastrobin, fluquinconazole, flucylazole flusilazole), flusulfamide, flutianil, flutolanil, flutriafol, fluxapyroxad, folpet, focetyl-aluminium, fuberidazole (flusilazole) fuberidazole), furalaxyl, furametpyr, furcarbanil, fluconazole, furconazole, fluconazole-cis, flumecyclox, furphanate, furphanate, gliodin, gliseofulvin (griseofulvin), guazatine (halacrinate), hexachlorobenzene (hexachlorobenzene), hexaconazole (hexaconazole), hexylthiophos (hexylthiofos), hydroxyquinoline sulfate (8-hydroxyquinoline sulfate), hymexazol (hymexazol), Imazalil, imibenconazole, iminoctadine-albe silate), iminoctadine-triacetate, impyruluxam, inpyrfluxam, ipconazole, ipfentrifluconazole, iprobenfos, iprodione, iprodione, iprovalicarb, iprovaricarb. isofetamid), isoflucypram, isoprothiolane, isopyrazam, isothianil, isovaledione, etc.

Bactericide (continued): kasugamycin, kresoxim-methyl, laminarin, mancopper, mancozeb, mandestrobin, mandipropamid, mannebu. maneb), mebenil, mecarbinzid, mefentrifluconazole, mepanipyrim, meptyldinocap, mepronil mepronil, metalaxyl-metalaxyl-metalaxyl-M. M), metam, metazoxolon, metconazole, methasulfocarb, methfuroxam, methyl isothiocyanate, metiram, metminostrobin , Metrafenone, metsulfovax, milneb, milneb, microbutanil, myclobutanil, microzoline, myclozolin, nabam, natamycin, nickel bis(dimethyldithiocarbamate) (nickel bis(dimethyldithiocarbamate) )), nitrostyrene, nitrothal-isopropyl, nuarimol, ocharimol, ochilinone, octhilinone, offurace, orysastrobin, oxathiapiproline. oxathiapiprolin), oxadixyl, organic copper (oxine copper), oxycarboxin, oxpoconazole fumarate, pefurzoate, penconazole enconazole), penflufen (penflufen), pencicuron (pencycuron), penthiopyrad (penthiopyrad), orthophenylphenol (o-phenylphenol), phosdiphen (phosdiphen), phthalide (phthalide), picarbutrazox (picarbutrazox), picoxystrobin ( picoxystrobin), piperalin, polycarbamate, polyoxins, polyoxorim, potassium azide, potassium hydrogen carbonate, proquinazid, probenazole. , Prochloraz, procymidone, propamocarb hydrochloride, propiconcarb, propiconazole, propineb, prothiocarb, prothioconazole, pidiflumetofen , Pyracarbolid, pyraclostrobin, pyrametostrobin, pyraoxystrobin, pyraziflumid, pyrazophos, pyribencarb-methyl, pyridinitrile. pyridinitril), pyrifenox, pyrimethanil, pyriminostrobin, pyrimorph, pyriophenone, pyrisoxazole, pyrroquilon, pyroxycyclol, pyroxychlor pyroxyfur), quinomethionate, quinofumelin, quinoxyf Quinoxyfen, quintozene, quinacetol-sulfate, quinazamid, quinconazole, rabenzazole and Bacillus subtilis, Strain:D747, FZB24, GZ HAI0404, MBI600, QST713, Y1336 etc.) etc.

Bactericide (continued): sedaxane, sodium azide, sodium hydrogen carbonate, sodium hypochlorite, sulfur, spiroxamine, salicylanilide. (Salycylanilide), silthiofam (silthiofam), simeconazole (temeconazole), tebuconazole (tebuconazole), tebufloquin (tebufloquin), tecnazene (tecnazene), tecoram (tecoram), tetraconazole (tetraconazole), thiabendazole (thiabendazole), thiabendazole, thiadifluor), thicyofen (thicyofen), thifluzamide (thifluzamide), thiochlorfenphim (thiochlorfenphim), thiophanate (thiophanate), thiophanate-methyl (thiophanate-methyl), thioquinox (thioquinox), thiram (thiram), thiazinyl (tiadinil), Thioxymid, tolclofos-methyl, tolprocarb, tolprocarb, tolylfluanid, triadimefon, triadimenol, triadimenol, triamifos, triazoxy, triazoxide. , Triazbutil, tributyltin oxide, trichlamide, tricyclazole, tridemorph, trifloxystrobin, triflumizole, triforine, tricloine. Pilicarb (triclopyricarb), triticonazole (triticonazole), validamycin (validamycin), valifenarate (valifenalate), vinclozo Phosphorus (vinclozolin), zarilamide (zinc sulfate), zinc sulfate (zinc sulfate), zineb (zineb), ziram (ziram), zoxamide (zoxamide), shiitake mycelium extract, shiitake fruiting body extract, ZF-9646 (test name) ), NF-180 (test name), MIF-1002 (test name), S-2399 (test name), AKD-5195 (test name) and NNF-0721 (test name).

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

Nematicides: aldoxycarb, benclothiaz, kazusaphos, cadusafos, davy cpee (DBCP), diclofenthion (dichlofenthion), dspepe (DSP), etoprophos (ethoprophos), fenamiphos (fenamiphos), fensulfothion. (Fensulfothion), fluazaindolizine, fluensulfone, fosthiazate, fosthietan, imicyafos, isamifofos, isamidofos, isazofos, oxamyloxamyl, oxamyloxamyl thiaxazafen), thionazin, tioxazafen, BYI-1921 (test name) and MAI-08015 (test name).

Acaricide: acequinocyl, acrinathrin, acinonapyr, acynonapyr, amidoflumet, amitraz, azocyclotin, BCI-033 (test name), benzoximate, Bifenazate, bromopropylate, bromopropylate, chinomethionat, chlorobezilate, clofentezine, cyenopyrafen, cyflumethofen, cyflumetofen, cyhexatineico, dichofol , Dienochlor, diflovidazin, denurovidazin, DNOC, etoxazole, fenazaquin, fenbutatin oxide, phenbutatin oxide, fenpropathrin, fenpropathrin, fenpyroximate (Fenpyroximate), fluacrypyrim (fluacrypyrim), halfenprox (halfenprox), hexythiazox (hexythiazox), milbemectin (milbemectin), propargite (propargite), pipflubumide (pyflubumide), pyridaben (pyridaben), pyrimidifen (pyrimidifen) -1870 (test name), spirodiclofen, spiromesifen, CL900167 (test name), tebufenpyrad and NA-89 (test name).

Insecticides: abamectin, acephate, acetamipirid, afidopyropen, afoxolaner, alanicarb, aldicarb, alphocin, azaiphos -Ethyl (azinphos-ethyl), azinphos-methyl, azillphos-methyl, bacillus thuringiensis, bendiocarb, benfluthrin, benfuracarb, bensultap, benzpyrimoxane benzpyrimoxan), bifenthrin, bioallethrin, bioresmethrin, bistrifluron, broflanilide, buprofezin, buprofezin, butocarboxim, carbaryl, carbaryl. carbofuran), carbosulfan, cartap, cartapran, chlorantraniliprole, chlorethxyfos, chlorfenapyr, chlorfenvinphos, chlorfluazuron ), chlormephos, chloroprallethrin, chlorpyrifos, chlorpyrifos-methyl, chromafenozide, clothianidin, cyanophos, cyantraniliprole, cyantraniliprole , Cyclaniliprole, cycloprothrin, cyflumethofen etofen), cyfluthrin, beta-cyfluthrin, beta-cyfluthrin, cyhalodiamide, cyhalothrin, lambda-cyhalothrin, lambda-cyhalothrin, cypermethrin, alpha-cypermethrin. ), beta-cypermethrin, zeta-cypermethrin, zife-cypermethrin, cyphenothrin, cyromazine, deltamethrin, diacloden, diafenthiuron. , Diazinon, dichloromezothiaz, dichlorromezotiaz, dichlorvos, diflubenzuron, dimefluthrin, dimethylvinphos, dinotefuran, diophenolan, diofenolan, disulfonolan, disulfonolan , Dimethoate, emamectin-benzoate, empenthrin, endosulfan, alpha-endosulfan, EPN, esfenvalerate, ethiofencarb, ethiofencarb, Ethhiprole, etofenprox, etrimfos, fenitrothion, fenitrothion, fenobucarb, phenoxycarb, fenpropathrin, fenthion, fenvalerate , Fipronil, flonicamid, fluazuron, flubendiamide, flusic Roxuron (flucycloxuron), flucytrinate (flucythrinate), flufenerim (flufenerim), flufenoxuron (flufenoxuron), flufenprox (flufenprox), flumethrin, fluralaner (fluralaner), fluvalinate, tau-fulvali Ate (tau-fluvalinate), honophos, formetanate, formothion, formothion, furathiocarb, flufiprole, fluhexafon, flupyradifurone, flometoquin, etc.

Insecticide (continued): gamma-cyhalothrin, halofenozide, heptafluthrin, hexaflumuron, hydramethylnon, imidacloprid, imiprothrin. , Isofenphos, indoxacarb, indoxacarb-MP, indoxacarb-MP, isoprocarb, isoxathion, kappa-bifenthrin, kappa-tefluthrin ), lepimectin, lufenuron, malathion, meperfluthrin, metaflumizone, metaflumizone, methamidophos, methidathion, methidathical, methidathical, methophath, methidathical ), methomyl, methoprene, methoxychlor, methoxyphenozide, methyl bromide, epsilon-metofluthrin, metofluthrin, momfluorothrin, momfluorothrin. Epsilon-momfluorothrin, monocrotophos, muscalure, nitenpyram, novaluron, noviflumuron, omethoate, oxamyl, oxydemethyl. (Oxydemeton-methyl), oxydeprofos, parathion, parathion-methyl thyl), pentachlorophenol(PCP), permethrin, permethrin, phenothrin, phenthoate, phenthoate, phoxim, phorate, phosalone, phosmet, phosphamidone phosphamidon), pirimicarb (pirimicarb), pirimiphos-methyl (pirimiphos-methyl), profenofos (profenofos), profluthrin (profluthrin), prothiofos (propthiofos), propaphos (propaphos), protrifenbute (protrifenbute), pymetrozine (pymetroz). Pyraclofos, Pyrethrins, Pyridalyl, Pyrifluquinazon, Pyriprole, Pyrafluprole, Pyriproxyfen, Resmethrin, Rotenone, Rotenone -0405 (Study name), sulprofos, silafluofen, spinetoram, spinosad, spiromesifen, spirotetramat, sulfoxaflor, sulfotep, sulfotep sulfotep), SYJ-159 (test name), tebufenozide (tebfenozide), teflubenzuron (teflubenzuron), tefluthrin (tefluthorin), terbufos (terbufos), tetrachlorovinphos (tetrachlorvinphos), tetramethrin (tetramethrin), d-T-80-. Phthalthrin (d-tetramethrin), tetramethylfluthrin (tetramethylfluthrin), tetraniliprole (tetraniliprole), thiacloprid (thiacloprid), thiocyclam (thiocyclam), thiodicarb (thiodicarb), Thiamethoxam, thiofanox, thiometon, tolfenpyrad, tralomethrin, transfluthrin, triazamate, trichlorfon, trichlorfon, triazuron, triazuron. Mezopyrim (triflumezopyrim), triflumuron (triflumuron), vamidothion (vamidothion), fluxamethamid (fluxametamide), MIE-1209 (test name), ME5382 (test name), etc.

Hereinafter, the present invention will be described in more detail by 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 Examples and Reference Examples used a medium pressure preparative device from Yamazen Co., Ltd.; YFLC-Wprep (flow rate 18 ml/min, silica gel 40 μm column).

Moreover, the chemical shift value of the proton nuclear magnetic resonance (NMR) in the synthesis example and the reference example is 300 MHz (model: ECX300 or ECP300, manufactured by JEOL) using Me ₄ Si (tetramethylsilane) as a reference substance. It was measured.

The symbols in the proton nuclear magnetic resonance chemical shift values have the following meanings.
s: singlet, brs: broad singlet, d: doublet, dd: double doublet, t: triplet, q: quartet, m: multiplet In addition, the solvent name used for NMR measurement is in parentheses in the data of chemical shift value. It was shown to.

Synthesis example 1: 2-[3-(ethylsulfonyl)-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-7-(trifluoromethyl)imidazo[1,2-c ] Synthesis of pyrimidine (invention compound No. 1-3-001a) 82 mg of 6-(trifluoromethyl)pyrimidin-4-amine was dissolved in 5 ml of chlorobenzene, and 2-bromo-1-[3-( 200 mg of ethylsulfonyl)-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]ethanone were added. After the addition was completed, the reaction mixture was stirred under heating under reflux for 9 hours. After completion of the reaction, 10 ml of 1M sodium hydroxide aqueous solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate (10 ml×2). The obtained organic layer was dehydrated and dried over saturated saline and then anhydrous sodium sulfate in this order, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate [gradient of 100:0 to 0:100 (volume ratio, the same applies hereinafter)], 163.5 mg of the target product was obtained as a flesh-colored solid.

Melting point: 235-237°C
¹ H-NMR(CDCl ₃ ): δ9.38(d, J=7.5Hz, 1H), 9.19(s, 1H), 8.63(s, 1H), 8.12-8.09(m, 1H), 8.02-8.00( m, 1H), 7.28-7.23(m, 1H), 3.73(q, J=7.4Hz, 2H), 1.34(t, J=7.4Hz, 3H).
Synthesis Example 2: 2-[3-(ethylthio)-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo [4,5-b]Pyridine (the present compound No. 1-1-002b) and 2-[3-(ethylsulfonyl)-7-(trifluoromethyl)imidazo[1,2-a]pyridine-2- Iyl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (inventive compound No. 1-1-002a) Step 1: 3-(ethylthio)-N - [2- (methylamino) -5- (trifluoromethyl) pyridin-3-yl] -7- (trifluoromethyl) synthesis of N ² imidazo [1,2-a] pyridine-2-carboxamide - methyl 856 mg of -5-(trifluoromethyl)pyridine-2,3-diamine was dissolved in 20 ml of pyridine, and 3-(ethylthio)-7-(trifluoromethyl)imidazo[1,2-a]pyridine-2 was dissolved at room temperature. -1.00 g of carboxylic acid, 1.32 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and 42 mg of 4-(dimethylamino)pyridine were added. After the addition was complete, the reaction mixture was stirred at room temperature for 6 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. 10 ml of water was added to the obtained residue, and the mixture was extracted with ethyl acetate (10 ml×2). The obtained organic layer was washed with 1M aqueous hydrochloric acid solution, dehydrated and dried over saturated saline and then anhydrous sodium sulfate in this order, and then the solvent was distilled off under reduced pressure to obtain 1.40 g of the crude product. Got This product was used as it was in the next step without further purification.

Step 2: 2-[3-(ethylthio)-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[ Synthesis of 4,5-b]pyridine (Compound No. 1-1-002b of the present invention) Crude 3-(ethylthio)-N-[2-(methylamino)-5-(tri Fluoromethyl)pyridin-3-yl]-7-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxamide (1.40 g) was dissolved in acetic acid (15 ml) and stirred under heating under reflux for 2 hours. .. After completion of stirring, the reaction mixture was stirred overnight at room temperature. After completion of stirring, the solid precipitated in the reaction mixture was filtered off by filtration. The obtained solid was washed with diisopropyl ether to obtain the target product (645 mg) as a white solid.

Melting point: 199-202°C
¹ H-NMR(CDCl ₃ ): δ8.78(d, J=7.2Hz, 1H), 8.73(d, J=1.5Hz, 1H), 8.40(d, J=2.0Hz, 1H), 8.06-8.04 (m, 1H), 7.21(dd, J=7.2, 1.5Hz, 1H), 4.33(s, 3H), 3.15(q, J=7.4Hz, 2H), 1.22(t, J=7.4Hz, 3H) .
Step 3: 2-[3-(ethylsulfonyl)-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo Synthesis of [4,5-b]pyridine (Compound No. 1-1-002a of the present invention) 2-[3-(ethylthio)-7-(trifluoromethyl)imidazo[1,2-a]pyridine-2- Yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine in a solution of 645 mg of chloroform in 15 ml of chloroform under ice cooling, 65% by mass of metachloroperbenzoic acid (about 30% by mass). % Water) (961 mg) was added. After the addition was complete, the reaction mixture was stirred at room temperature for 2.5 hours. After completion of the reaction, saturated aqueous sodium thiosulfate solution was added to the reaction mixture, and the mixture was extracted with chloroform (10 ml). The obtained organic layer was washed with a 1 M aqueous sodium hydroxide solution, dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient of 100:0 to 50:50) to obtain 660 mg of the desired product as a white solid.

Melting point: 203-205°C
¹ H-NMR(CDCl ₃ ): δ9.42(d, J=7.5Hz, 1H), 8.77(s, 1H), 8.36(d, J=1.7Hz, 1H), 8.16(s, 1H), 7.32 (dd, J=7.5, 1.7Hz, 1H), 4.18(s, 3H), 4.11(q, J=7.5Hz, 2H), 1.47(t, J=7.5Hz, 3H).
Synthesis Example 3: 2-[3-(ethylthio)-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-5-[(trifluoromethyl)thio]benzo[d]oxazole (Invention compound No. 1-2-003b), 2-[3-(ethylsulfonyl)-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-5-[(tri Fluoromethyl)sulfinyl]benzo[d]oxazole (invention compound No. 1-2-002a) and 2-[3-(ethylsulfonyl)-6-(trifluoromethyl)imidazo[1,2-a]pyridine- Synthesis of 2-yl]-5-[(trifluoromethyl)sulfonyl]benzo[d]oxazole (inventive compound No. 1-2-001a) Step 1: 3-(ethylthio)-N-{2-hydroxy- Synthesis of 5-[(trifluoromethyl)thio]phenyl}-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxamide 2-amino-4-[(trifluoromethyl)thio] Phenol 466 mg was dissolved in pyridine 10 ml, and at room temperature, 3-(ethylthio)-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylic acid 356 mg, 1-ethyl-3-(3- 471 mg of dimethylaminopropyl)carbodiimide hydrochloride and 75 mg of 4-(dimethylamino)pyridine were added. After the addition was complete, the reaction mixture was stirred at room temperature overnight. After completion of the reaction, the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient of 100:0 to 0:100) to obtain 100 mg of the desired product as a reddish brown solid. ..

Step 2: 2-[3-(ethylthio)-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-5-[(trifluoromethyl)thio]benzo[d]oxazole( Synthesis of compound of the present invention No. 1-2-003b) 3-(ethylthio)-N-{2-hydroxy-5-[(trifluoromethyl)thio]phenyl}-6-(trifluoromethyl)imidazo[1, A solution of 89 mg of 2-a]pyridine-2-carboxamide in 5 ml of tetrahydrofuran was heated to 50° C., and 65 mg of bis(2-methoxyethyl)azodicarboxylate and 73 mg of triphenylphosphine were added.

After the addition was complete, the reaction mixture was stirred at 50° C. for 3 hours. After completion of stirring, the reaction mixture was stirred overnight at room temperature. After completion of the reaction, 10 ml of water was added to the reaction mixture, and the mixture was extracted with ethyl acetate (10 ml×2). The obtained organic layer was dehydrated and dried over saturated saline and then anhydrous sodium sulfate in this order, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient of 85:15 to 0:100) to obtain 21 mg of the desired product as a light brown solid. ..

¹ H-NMR(CDCl ₃ ): δ8.96(s, 1H), 8.23(s, 1H), 8.00-7.45(m, 4H), 3.11(q, J=7.4Hz, 2H), 1.26(t, J=7.4Hz, 3H).
Step 3: 2-[3-(ethylsulfonyl)-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-5-[(trifluoromethyl)sulfinyl]benzo[d]oxazole (Inventive compound No. 1-2-002a) and 2-[3-(ethylsulfonyl)-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-5-[(tri Synthesis of Fluoromethyl)sulfonyl]benzo[d]oxazole (Compound of the Invention No. 1-2-001a) 2-[3-(Ethylthio)-6-(trifluoromethyl)imidazo[1,2-a]pyridine- 67 mg of 65% by weight metachloroperbenzoic acid (containing about 30% by weight of water) in a solution of 21 mg of 2-yl]-5-[(trifluoromethyl)thio]benzo[d]oxazole in 5 ml of chloroform at room temperature. Was added. After the addition was complete, the reaction mixture was stirred at room temperature overnight. After completion of stirring, the reaction mixture was continuously stirred for 2 hours while heating under reflux. After completion of the reaction, saturated aqueous sodium thiosulfate solution was added to the reaction mixture, and the mixture was extracted with chloroform (10 ml). The obtained organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution, dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient of 100:0 to 50:50) to obtain the desired product, 2-[3-(. Ethylsulfonyl)-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-5-[(trifluoromethyl)sulfinyl]benzo[d]oxazole 5 mg and the desired product, 2-[ 13 mg of 3-(ethylsulfonyl)-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-5-[(trifluoromethyl)sulfonyl]benzo[d]oxazole were each light brown. Obtained as a solid.

2- [3- (ethylsulfonyl) -6- (trifluoromethyl) imidazo [1,2-a] pyridin-2-yl] -5 - [(trifluoromethyl) sulfinyl] benzo [d] ¹ oxazole H -NMR(CDCl ₃ ): δ9.75(s, 1H), 8.37(s, 1H), 8.05-7.35(m, 4H), 4.09(q, J=7.5Hz, 2H), 1.48(t, J= 7.5Hz, 3H).
2- [3- (ethylsulfonyl) -6- (trifluoromethyl) imidazo [1,2-a] pyridin-2-yl] -5 - [(trifluoromethyl) sulfonyl] benzo [d] ¹ oxazole H -NMR(CDCl ₃ ): δ9.74(s, 1H), 8.62(s, 1H), 8.25-7.40(m, 4H), 4.07(q, J=7.5Hz, 2H), 1.50(t, J= 7.5Hz, 3H).
Synthesis Example 4: 5-(Ethylthio)-6-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl]-2-(trifluoromethyl)imidazo [2,1-b]Thiazole (Compound No. 2-1-001b of the present invention) and 5-(ethylsulfonyl)-6-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5] -B]Pyridin-2-yl]-2-(trifluoromethyl)imidazo[2,1-b]thiazole (inventive compound No. 2-1-001a) Step 1: 5-(ethylthio)-N - synthesis of [2- (methylamino) -5- (trifluoromethyl) pyridin-3-yl] -2- (trifluoromethyl) imidazo [2,1-b] thiazole-6-carboxamide N ² - methyl 242 mg of 5-(trifluoromethyl)pyridine-2,3-diamine was dissolved in 10 ml of pyridine, and 5-(ethylthio)-2-(trifluoromethyl)imidazo[2,1-b]thiazole-6 was dissolved at room temperature. -250 mg of carboxylic acid, 322 mg of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and 10 mg of 4-(dimethylamino)pyridine. After the addition was complete, the reaction mixture was stirred at room temperature overnight. After completion of the reaction, the solvent was distilled off under reduced pressure. 10 ml of water was added to the obtained residue, and the mixture was extracted with ethyl acetate (10 ml×2). The obtained organic layer was washed with a 1M aqueous hydrochloric acid solution, dehydrated and dried over saturated saline and then anhydrous sodium sulfate in this order, and then the solvent was distilled off under reduced pressure to obtain the desired product, 5-(ethylthio). A crude product of -N-[2-(methylamino)-5-(trifluoromethyl)pyridin-3-yl]-2-(trifluoromethyl)imidazo[2,1-b]thiazole-6-carboxamide was obtained. Obtained. This product was used as it was in the next step without further purification.

Step 2: 5-(ethylthio)-6-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl]-2-(trifluoromethyl)imidazo[ Synthesis of 2,1-b]thiazole (inventive compound No. 2-1-001b) The crude product of 5-(ethylthio)-N-[2-(methylamino)-5-(tri Fluoromethyl)pyridin-3-yl]-2-(trifluoromethyl)imidazo[2,1-b]thiazole-6-carboxamide was dissolved in 10 ml of acetic acid, and the mixture was stirred under heating under reflux for 4.5 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. To the obtained residue, 10 ml of 1M aqueous hydrochloric acid solution was added, and the mixture was extracted with ethyl acetate (10 ml×2). The obtained organic layer was dehydrated and dried over saturated saline and then anhydrous sodium sulfate in this order, and then the solvent was distilled off under reduced pressure. The precipitated solid was filtered off by filtration. The obtained solid was washed with diisopropyl ether to obtain the desired product (332 mg) as a white solid.

Melting point: 200-203°C
¹ H-NMR(CDCl ₃ ): δ8.72-8.67(m, 1H), 8.37-8.33(m, 1H), 8.12-8.08(m, 1H), 4.25(s, 3H), 3.14(q, J =7.5Hz, 2H), 1.25(t, J=7.5Hz, 3H).
Step 3: 5-(ethylsulfonyl)-6-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl]-2-(trifluoromethyl)imidazo Synthesis of [2,1-b]thiazole (Compound No. 2-1-001a of the Present Invention) 5-(Ethylthio)-6-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5] -B]pyridin-2-yl]-2-(trifluoromethyl)imidazo[2,1-b]thiazole (132 mg) in a solution of chloroform (3 ml) under ice-cooling, 65% by mass of metachloroperbenzoic acid (about 30% by mass). % Water) was added. After the addition was complete, the reaction mixture was stirred at room temperature for 1.5 hours. After completion of the reaction, saturated aqueous sodium thiosulfate solution was added to the reaction mixture, and the mixture was extracted with chloroform (10 ml). The obtained organic layer was washed with a 1 M aqueous sodium hydroxide solution, dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient 100:0 to 50:50) to obtain 110 mg of the desired product as a white solid.

Melting point: 249-251°C
¹ H-NMR(CDCl ₃ ): δ8.76-8.71(m, 1H), 8.71-8.66(m, 1H), 8.36-8.32(m, 1H), 4.23(s, 3H), 4.19(q, J =7.5Hz, 2H), 1.45(t, J=7.5Hz, 3H).
Synthesis Example 5: 2-[3-(ethylsulfonyl)-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-7-(trifluoromethyl)imidazo[1,2-b ] Synthesis of Pyridazine (Compound No. 1-4-001a of the Present Invention) 82 mg of 5-(trifluoromethyl)pyridazin-3-amine was dissolved in 5 ml of chlorobenzene, and 2-bromo-1-[3- 200 mg of (ethylsulfonyl)-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]ethanone were added. After the addition was completed, the reaction mixture was stirred under heating to reflux for 3 hours. After completion of the reaction, 10 ml of 1M sodium hydroxide aqueous solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate (10 ml×2). The obtained organic layer was dehydrated and dried over saturated saline and then anhydrous sodium sulfate in this order, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient of 100:0 to 0:100) to obtain 142 mg of the desired product as a brown solid.

Melting point: 214-218°C
¹ H-NMR(CDCl ₃ ): δ9.40(d, J=7.5Hz, 1H), 8.94(s, 1H), 8.58(d, J=2.0Hz, 1H), 8.34-8.30(m, 1H) , 8.11-8.09(m, 1H), 7.24(dd, J=7.5, 2.0Hz, 1H), 3.79(q, J=7.4Hz, 2H), 1.36(t, J=7.4Hz, 3H).
Synthesis Example 6: 2-[3-(ethylthio)-6-(trifluoromethyl)imidazo[1,2-a]pyrazin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo [4,5-b]Pyridine (Compound No. 1-1-029b of the present invention) and 2-[3-(ethylsulfonyl)-6-(trifluoromethyl)imidazo[1,2-a]pyrazine-2- [Ill]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (inventive compound No. 1-1-029a) Step 1: 3-(ethylthio)-N - synthesis of [2- (methylamino) -5- (trifluoromethyl) pyridin-3-yl] -6- (trifluoromethyl) imidazo [1,2-a] pyrazine-2-carboxamide N ² - methyl 271 mg of -5-(trifluoromethyl)pyridine-2,3-diamine was dissolved in 10 ml of pyridine, and 3-(ethylthio)-6-(trifluoromethyl)imidazo[1,2-a]pyrazine-2 was dissolved at room temperature. -270 mg of carboxylic acid and 357 mg of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride were added. After the addition was complete, the reaction mixture was stirred at room temperature for 2 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. 10 ml of water was added to the obtained residue, and the mixture was extracted with ethyl acetate (10 ml×2). The obtained organic layer was dehydrated and dried over saturated saline and then anhydrous sodium sulfate in this order, and then the solvent was distilled off under reduced pressure to give 3-(ethylthio)-N-[2-(methylamino)- A crude product of 5-(trifluoromethyl)pyridin-3-yl]-6-(trifluoromethyl)imidazo[1,2-a]pyrazine-2-carboxamide was obtained. This product was used as it was in the next step without further purification.

Step 2: 2-[3-(ethylthio)-6-(trifluoromethyl)imidazo[1,2-a]pyrazin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[ Synthesis of 4,5-b]pyridine (Compound of the present invention No. 1-1-029b) 3-(ethylthio)-N-[2-(methylamino)-5-(tri Fluoromethyl)pyridin-3-yl]-6-(trifluoromethyl)imidazo[1,2-a]pyrazine-2-carboxamide was dissolved in 10 ml of acetic acid and stirred under heating under reflux for 17 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. 10 ml of water was added to the obtained residue, and the mixture was extracted with ethyl acetate (10 ml×2). The obtained organic layer was dehydrated and dried over saturated saline and then anhydrous sodium sulfate in this order, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient of 100:0 to 80:20) to obtain 257 mg of the desired product as a white solid.

Melting point: 220-222°C
¹ H-NMR(CDCl ₃ ): δ9.24(s, 1H), 8.99(s, 1H), 8.76(d, J=1.5Hz, 1H), 8.42(d, J=1.5Hz, 1H), 4.37 (s, 3H), 3.26(q, J=7.5Hz, 2H), 1.25(t, J=7.5Hz, 3H).
Step 3: 2-[3-(ethylsulfonyl)-6-(trifluoromethyl)imidazo[1,2-a]pyrazin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo Synthesis of [4,5-b]pyridine (Compound No. 1-1-029a of the present invention) 2-[3-(ethylthio)-6-(trifluoromethyl)imidazo[1,2-a]pyrazine-2- Yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine in a solution of 232 mg of chloroform in 5 ml of chloroform, under ice cooling, 65% by mass of metachloroperbenzoic acid (about 30% by mass). % Water) 326 mg was added. After the addition was complete, the reaction mixture was stirred at room temperature for 2 hours. After completion of the reaction, saturated aqueous sodium thiosulfate solution was added to the reaction mixture, and the mixture was extracted with chloroform (10 ml). The obtained organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution, dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. Diisopropyl ether (10 ml) was added to the obtained solid, and the mixture was filtered to obtain 203 mg of the desired product as a white solid.

Melting point: 234-236°C
¹ H-NMR(CDCl ₃ ): δ9.63(s, 1H), 9.39(s, 1H), 8.81-8.77(m, 1H), 8.39-8.36(m, 1H), 4.25(s, 3H), 4.23(q, J=7.5Hz, 2H), 1.49(t, J=7.5Hz, 3H).
Synthesis Example 7: 2-[6-Bromo-3-(ethylthio)-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl) -3H-imidazo[4,5-b]pyridine (inventive compound No. 1-1-023b) and 2-[6-bromo-3-(ethylsulfonyl)-7-(trifluoromethyl)imidazo[1, Synthesis of 2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (invention compound No. 1-1-023a) Step 1 : 6-Bromo-N-[2-(methylamino)-5-(trifluoromethyl)pyridin-3-yl]-7-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxamide synthesis N ² - methyl-5- (trifluoromethyl) pyridine-2,3-diamine 1.51g dissolved in pyridine 20 ml, 6- bromo-7 at room temperature (trifluoromethyl) imidazo [1, 2 -A] 2.04 g of pyridine-2-carboxylic acid and 2.53 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride were added. After the addition was complete, the reaction mixture was stirred at room temperature for 3 hours. After completion of the reaction, 20 ml of water was added to the reaction mixture, and the precipitated solid was filtered off by filtration to obtain 2.98 g of the desired product as a skin-colored solid.

Melting point: 200-205°C
¹ H-NMR(CDCl ₃ ): δ8.77(brs, 1H), 8.54(s, 1H), 8.40-8.36(m, 1H), 8.28(s, 1H), 8.04(s, 1H), 7.85( d, J=2.0Hz, 1H), 5.20(brs, 1H), 3.10(d, J=4.8Hz, 3H).
Step 2: 2-[6-Bromo-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4. Synthesis of 5-b]pyridine 6-Bromo-N-[2-(methylamino)-5-(trifluoromethyl)pyridin-3-yl]-7-(trifluoromethyl)imidazo[1,2-a] 2.93 g of pyridine-2-carboxamide was dissolved in 15 ml of acetic acid, and the mixture was stirred with heating under reflux for 2 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. 10 ml of water was added to the obtained residue, and the mixture was extracted with chloroform (10 ml×2). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient of 100:0 to 0:100) to give 2.82 g of the desired product as a light brown solid. Obtained.

Melting point: 220-225°C
¹ H-NMR(CDCl ₃ ): δ8.71(d, J=1.4Hz, 1H), 8.55(s, 1H), 8.51(s, 1H), 8.27(d, J=1.4Hz, 1H), 8.14 (s, 1H), 4.47(s, 3H).
Step 3: 2-[6-Bromo-3-(ethylthio)-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl)- Synthesis of 3H-imidazo[4,5-b]pyridine (Compound No. 1-1-023b of the present invention) 518 mg of N-chlorosuccinimide was dissolved in 5 ml of 1,2-dichloroethane, and 321 mg of ethanethiol was added at -40°C. Was added. After the addition was complete, the reaction mixture was stirred at room temperature for 30 minutes. After completion of stirring, the reaction mixture was stirred at room temperature with 2-[6-bromo-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoro). A solution of 300 mg of methyl)-3H-imidazo[4,5-b]pyridine in 2 ml of 1,2-dichloroethane was added. After the addition was completed, the reaction mixture was stirred under heating to reflux for 3 hours. After completion of stirring, 1.04 g of N-chlorosuccinimide prepared in another container and a solution of 642 mg of ethanethiol in 5 ml of 1,2-dichloroethane were added to the reaction mixture at room temperature. After the addition was completed, the reaction mixture was stirred under heating to reflux for 3 hours. After completion of the reaction, 10 ml of water was added to the reaction mixture, and the mixture was extracted with chloroform (10 ml×2). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient of 100:0 to 0:100) to obtain 212 mg of the desired product as a white solid.

Melting point: 214-215°C
¹ H-NMR(CDCl ₃ ): δ8.93(s, 1H), 8.74(d, J=1.4Hz, 1H), 8.40(d, J=1.4Hz, 1H), 8.13(s, 1H), 4.33 (s, 3H), 3.18(q, J=7.4Hz, 2H), 1.24(t, J=7.4Hz, 3H).
Step 4: 2-[6-Bromo-3-(ethylsulfonyl)-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl) Synthesis of -3H-imidazo[4,5-b]pyridine (Compound No. 1-1-023a of the present invention) 2-[6-Bromo-3-(ethylthio)-7-(trifluoromethyl)imidazo[1, 2-A]Pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine 150 mg in a solution of chloroform 5 ml under ice cooling 65% by mass. 175 mg of metachloroperbenzoic acid (containing about 30% by weight of water) were added. After the addition was complete, the reaction mixture was stirred at room temperature for 2 hours. After completion of the reaction, saturated aqueous sodium thiosulfate solution was added to the reaction mixture, and the mixture was extracted with chloroform (10 ml). The obtained organic layer was washed with a 1 M aqueous sodium hydroxide solution, dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient of 100:0 to 0:100) to obtain 142 mg of the desired product as a white solid.

Melting point: 226-228°C
¹ H-NMR(CDCl ₃ ): δ9.60(s, 1H), 8.77(d, J=1.4Hz, 1H), 8.36(d, J=1.4Hz, 1H), 8.23(s, 1H), 4.19 (s, 3H), 4.15(q, J=7.5Hz, 2H), 1.49(t, J=7.5Hz, 3H).
Synthesis Example 8: 2-[3-(ethylthio)-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-5-(trifluoromethyl)-3H-imidazo[4,5] -B]Pyridine (the present compound No. 1-1-031b), 2-[3-(ethylthio)-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-1- Methyl-5-(trifluoromethyl)-1H-imidazo[4,5-b]pyridine (inventive compound No. 1-7-001b) and 2-[3-(ethylthio)-7-(trifluoromethyl) Imidazo[1,2-a]pyridin-2-yl]-3-methyl-5-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (inventive compound No. 1-1-030b) Step 1: N-[2-amino-6-(trifluoromethyl)pyridin-3-yl]-3-ethylthio-7-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxy Synthesis of amide 6-(trifluoromethyl)pyridine-2,3-diamine (712 mg) was dissolved in pyridine (10 ml), and 3-(ethylthio)-7-(trifluoromethyl)imidazo[1,2-a]pyridine was dissolved at room temperature. 972 mg of 2-carboxylic acid and 1.32 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride were added. After the addition was complete, the reaction mixture was stirred at room temperature overnight. After completion of the reaction, 20 ml of water was added to the reaction mixture, and the precipitated solid was filtered off by filtration to obtain 1.20 g of the target product as a crude product as a reddish brown solid. This product was used as it was in the next step without further purification.

Step 2: 2-[3-(ethylthio)-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-5-(trifluoromethyl)-3H-imidazo[4,5- b] Synthesis of pyridine (inventive compound No. 1-1-031b) N-[2-amino-6-(trifluoromethyl)pyridin-3-yl]-3-ethylthio of the crude product obtained in Step 1 1.2 g of -7-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxamide was dissolved in 10 ml of propionic acid, and the mixture was stirred with heating under reflux for 3 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. 10 ml of water was added to the obtained residue, and the mixture was extracted with ethyl acetate (10 ml×2). The obtained organic layer was washed with a 1M aqueous sodium hydroxide solution, dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 1.0 g of the target substance as a brown solid. This product was directly used in the next step without further purification.

¹ H-NMR(CDCl ₃ ): δ8.59(d, J=7.2Hz, 1H), 8.03(d, J=7.8Hz, 1H), 7.83(s, 1H), 7.36(d, J=7.8Hz , 1H), 7.04-6.98(m, 1H), 3.02(q, J=7.4Hz, 2H), 1.05(t, J=7.4Hz, 3H) (NH proton peak could not be observed).
Step 3: 2-[3-(ethylthio)-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-1-methyl-5-(trifluoromethyl)-1H-imidazo[ 4,5-b]Pyridine (the present compound No. 1-7-001b) and 2-[3-(ethylthio)-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl] Synthesis of 3-methyl-5-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (inventive compound No. 1-1-030b) 63% by mass sodium hydride (dispersed in mineral oil) To a solution of 66 mg of N,N-dimethylformamide in 3 ml, 2-[3-(ethylthio)-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-5-under ice cooling. A solution of (trifluoromethyl)-3H-imidazo[4,5-b]pyridine (500 mg) in N,N-dimethylformamide (7 ml) was added. After the addition was completed, the reaction mixture was stirred under ice cooling for 30 minutes. After completion of stirring, 286 mg of methyl trifluoromethanesulfonate was added to the reaction mixture under ice cooling. After the addition was complete, the reaction mixture was stirred at room temperature for 1.5 hours. After completion of the reaction, 10 ml of water was added to the reaction mixture, and the mixture was extracted with ethyl acetate (10 ml×2). The obtained organic layer was dehydrated and dried over saturated saline and then anhydrous sodium sulfate in this order, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient of 100:0 to 50:50) to obtain the desired product, 2-[3-(. Ethylthio)-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-1-methyl-5-(trifluoromethyl)-1H-imidazo[4,5-b]pyridine 150 mg and The desired product, 2-[3-(ethylthio)-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3-methyl-5-(trifluoromethyl)-3H-imidazo 218 mg of [4,5-b]pyridine were obtained as a brown solid and a white solid, respectively.

2-[3-(ethylthio)-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-1-methyl-5-(trifluoromethyl)-1H-imidazo[4,5] -B] Melting point of pyridine: 164-166°C
¹ H-NMR(CDCl ₃ ): δ8.81(d, J=7.5Hz, 1H), 8.03(s, 1H), 7.91(d, J=8.2Hz, 1H), 7.70(d, J=8.2Hz , 1H), 7.20(dd, J=7.5, 1.7Hz, 1H), 4.31(s, 3H), 3.35(q, J=7.4Hz, 2H), 1.24(t, J=7.4Hz, 3H).
2-[3-(ethylthio)-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3-methyl-5-(trifluoromethyl)-3H-imidazo[4,5] -B] melting point of pyridine: 163-165°C
¹ H-NMR(CDCl ₃ ): δ8.77(d, J=7.2Hz, 1H), 8.26(d, J=8.2Hz, 1H), 8.06(s, 1H), 7.68(d, J=8.2Hz , 1H), 7.21(dd, J=7.2, 1.5Hz, 1H), 4.33(s, 3H), 3.12(q, J=7.4Hz, 2H), 1.20(t, J=7.4Hz, 3H).
Synthesis Example 9: 2-[3-(ethylthio)-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo [4,5-c]Pyridine (Compound No. 1-8-005b of the present invention) and 2-[3-(ethylsulfonyl)-7-(trifluoromethyl)imidazo[1,2-a]pyridine-2- [Ill]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine (Compound of the present invention No. 1-8-005a) Step 1: 3-(Ethylthio)-N - [5- (methylamino) -2- (trifluoromethyl) pyridin-4-yl] -7 synthesis of (trifluoromethyl) imidazo [1,2-a] pyridine-2-carboxamide N ³ - methyl 303 mg of -6-(trifluoromethyl)pyridine-3,4-diamine was dissolved in 15 ml of pyridine, and 3-(ethylthio)-7-(trifluoromethyl)imidazo[1,2-a]pyridine-2 was dissolved at room temperature. -552 mg of carboxylic acid and 732 mg of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride were added. After the addition was complete, the reaction mixture was stirred at room temperature overnight. After completion of the reaction, the solvent was distilled off under reduced pressure. 10 ml of water was added to the obtained residue, and the mixture was extracted with chloroform (10 ml×2). The obtained organic layer was dried over anhydrous sodium sulfate and dried, and then the solvent was distilled off under reduced pressure to obtain 986 mg of a target product as a crude product. This product was used as it was in the next step without further purification.

Step 2: 2-[3-(ethylthio)-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[ Synthesis of 4,5-c]pyridine (Compound of the present invention No. 1-8-005b) 3-(ethylthio)-N-[5-(methylamino)-2-(tri) of the crude product obtained in Step 1 986 mg of fluoromethyl)pyridin-4-yl]-7-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxamide was dissolved in 15 ml of acetic acid, and the mixture was stirred for 22 hours while heating under reflux. After completion of stirring, the reaction mixture was stirred overnight at room temperature. After completion of the reaction, the solvent was distilled off under reduced pressure. 10 ml of water was added to the obtained residue, and the mixture was extracted with chloroform (10 ml×2). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient of 100:0 to 70:30) to obtain 358 mg of the desired product as a yellow solid.

Melting point: 217-219°C
¹ H-NMR(CDCl ₃ ): δ8.97(s, 1H), 8.78(d, J=7.2Hz, 1H), 8.20(s, 1H), 8.05(s, 1H), 7.22(d, J= 7.2Hz, 1H), 4.37(s, 3H), 3.15(q, J=7.5Hz, 2H), 1.22(t, J=7.5Hz, 3H).
Step 3: 2-[3-(ethylsulfonyl)-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo Synthesis of [4,5-c]pyridine (inventive compound No. 1-8-005a) 2-[3-(ethylthio)-7-(trifluoromethyl)imidazo[1,2-a]pyridine-2- Yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine in a solution of 258 mg of chloroform in 8 ml of chloroform under ice cooling, 65% by mass of metachloroperbenzoic acid (about 30% by mass). % Water) 323 mg. After the addition was complete, the reaction mixture was stirred at room temperature for 1 hour. After completion of the reaction, saturated aqueous sodium thiosulfate solution was added to the reaction mixture, and the mixture was extracted with chloroform (10 ml). The obtained organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution, dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient 100:0 to 50:50). To the obtained solid, 10 ml of diisopropyl ether was added and filtered to obtain 200 mg of the desired product as a yellow solid.

Melting point: 245-247°C
¹ H-NMR(CDCl ₃ ): δ9.39(d, J=7.2Hz, 1H), 9.00(s, 1H), 8.14(s, 2H), 7.33(d, J=7.2Hz, 1H), 4.20 (s, 3H), 4.07(q, J=7.5Hz, 2H), 1.46(t, J=7.5Hz, 3H).
Synthesis Example 10: 2-[3-(ethylthio)-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3,4-dimethyl-6-(trifluoromethyl)-3H -Imidazo[4,5-c]pyridine (the compound of the present invention No. 1-8-003b) and 2-[3-(ethylsulfonyl)-6-(trifluoromethyl)imidazo[1,2-a]pyridine- 2-yl]-3,4-dimethyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine (invention compound No. 1-8-003a) Step 1:3-( Ethylthio)-N-[2-methyl-3-(methylamino)-6-(trifluoromethyl)pyridin-4-yl]-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2- carboxamide synthesis N ³ of, 2-dimethyl-6- (trifluoromethyl) pyridine-3,4-diamine 212mg was dissolved in pyridine 10 ml, at room temperature 3- (ethylthio) -6- (trifluoromethyl) imidazo 200 mg of [1,2-a]pyridine-2-carboxylic acid, 264 mg of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and 9 mg of 4-(dimethylamino)pyridine were added. After the addition was complete, the reaction mixture was stirred at room temperature overnight. After completion of the reaction, the solvent was distilled off under reduced pressure. 10 ml of water was added to the obtained residue, and the mixture was extracted with ethyl acetate (10 ml×2). After dehydrating and drying the obtained organic layer with anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and 3-(ethylthio)-N-[2-methyl-3-(methylamino)-6-(trifluoro A crude product of methyl)pyridin-4-yl]-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxamide was obtained. This product was used as it was in the next step without further purification.

Step 2: 2-[3-(ethylthio)-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3,4-dimethyl-6-(trifluoromethyl)-3H-. Synthesis of Imidazo[4,5-c]pyridine (Compound of the present invention No. 1-8-003b) 3-(ethylthio)-N-[2-methyl-3-(methylamino) of the crude product obtained in Step 1 )-6-(Trifluoromethyl)pyridin-4-yl]-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxamide was dissolved in 10 ml of acetic acid and heated under reflux to give 3 Stir for hours. After completion of the reaction, the solvent was distilled off under reduced pressure. 10 ml of water was added to the obtained residue, and the mixture was extracted with ethyl acetate (10 ml×2). The obtained organic layer was dehydrated and dried over saturated saline and then anhydrous sodium sulfate in this order, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient of 100:0 to 70:30) to obtain 85 mg of the desired product as a white solid.

Melting point: 169-171°C
¹ H-NMR(CDCl ₃ ): δ9.01(s, 1H), 8.03(s, 1H), 7.83(d, J=9.3Hz, 1H), 7.54(dd, J=9.3, 1.8Hz, 1H) , 4.41(s, 3H), 3.10(q, J=7.5Hz, 2H), 3.08(s, 3H), 1.22(t, J=7.5Hz, 3H).
Step 3: 2-[3-(ethylsulfonyl)-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3,4-dimethyl-6-(trifluoromethyl)-3H. -Synthesis of imidazo[4,5-c]pyridine (inventive compound No. 1-8-003a) 2-[3-(ethylthio)-6-(trifluoromethyl)imidazo[1,2-a]pyridine- 2-yl]-3,4-dimethyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine 49 mg solution in chloroform 3 ml under ice cooling 65 wt% metachloroperbenzoic acid 57 mg (containing about 30% by weight of water) were added. After the addition was complete, the reaction mixture was stirred at room temperature for 2 hours. After completion of the reaction, saturated aqueous sodium thiosulfate solution was added to the reaction mixture, and the mixture was extracted with chloroform (10 ml). The obtained organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution, dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient of 100:0 to 50:50) to obtain 37 mg of the desired product as a white solid.

Melting point: 200-205°C
¹ H-NMR(CDCl ₃ ): δ9.59(s, 1H), 7.97(s, 1H), 7.96(d, J=9.6Hz, 1H), 7.74(dd, J=9.6, 1.5Hz, 1H) , 4.25(s, 3H), 3.96(q, J=7.5Hz, 2H), 3.08(s, 3H), 1.45(t, J=7.5Hz, 3H).
Synthesis Example 11: 3-(ethylsulfonyl)-6,7'-bis(trifluoromethyl)-2,2'-biimidazo[1,2-a]pyridine (invention compound No. 1-5-002a) Synthesis 4-(trifluoromethyl)pyridin-2-amine 102 mg was dissolved in bromobenzene 4 ml, and 2-bromo-1-[3-(ethylsulfonyl)-6-(trifluoromethyl)imidazo[1 was dissolved at room temperature. , 2-a]Pyridin-2-yl]ethanone (300 mg) was added. After the addition was completed, the reaction mixture was stirred with heating under reflux for 5 hours. After completion of the reaction, 10 ml of 1M sodium hydroxide aqueous solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate (10 ml×2). The obtained organic layer was dehydrated and dried over saturated saline and then anhydrous sodium sulfate in this order, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient of 100:0 to 50:50) to obtain 168 mg of the desired product as a white solid.

Melting point: 245-248°C
¹ H-NMR(CDCl ₃ ): δ9.65(s, 1H), 8.57(s, 1H), 8.30(d, J=7.2Hz, 1H), 8.01(s, 1H), 7.90(d, J= 9.6Hz, 1H), 7.63(dd, J=9.6, 1.8Hz, 1H), 7.03(dd, J=7.2, 1.8Hz, 1H), 3.73(q, J=7.5Hz, 2H), 1.33(t, (J=7.5Hz, 3H).
Synthesis Example 12: 2-[3-(ethylsulfonyl)-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-7-(perfluoroethyl)imidazo[1,2-c ] Pyrimidine (the present invention compound No. 1-3-008a) and 3-bromo-2-[3-(ethylsulfonyl)-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl] Synthesis of -7-(perfluoroethyl)imidazo[1,2-c]pyrimidine (present compound No. 1-3-3-010a) Step 1: 2-[3-(ethylsulfonyl)-6-(trifluoromethyl) ) Synthesis of imidazo[1,2-a]pyridin-2-yl]-7-(perfluoroethyl)imidazo[1,2-c]pyrimidine (inventive compound No. 1-3-008a) 6-(per) 800 mg of fluoroethyl)pyrimidin-4-amine was dissolved in 10 ml of chlorobenzene, and 2-bromo-1-[3-(ethylsulfonyl)-6-(trifluoromethyl)imidazo[1,2-a]pyridine was dissolved at room temperature. -2-yl]ethanone 1780 mg was added. After the addition was completed, the reaction mixture was stirred under heating to reflux for 3 hours. After completion of the reaction, 10 ml of 1M sodium hydroxide aqueous solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate (10 ml×2). The obtained organic layer was dehydrated and dried over saturated saline and then anhydrous sodium sulfate in this order, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient 100:0 to 50:50) to obtain 926 mg of the desired product as a yellow solid.

Melting point: 233-239°C
¹ H-NMR(CDCl ₃ ): δ9.63(s, 1H), 9.19(s, 1H), 8.64(s, 1H), 8.05(s, 1H), 7.92(d, J=9.6Hz, 1H) , 7.66(dd, J=9.6, 1.5Hz, 1H), 3.72(q, J=7.5Hz, 2H), 1.35(t, J=7.5Hz, 3H).
Step 2: 3-Bromo-2-[3-(ethylsulfonyl)-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-7-(perfluoroethyl)imidazo[1, Synthesis of 2-c]pyrimidine (the present compound No. 1-3-3-010a) 2-[3-(ethylsulfonyl)-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl] To a solution of 150 mg of -7-(perfluoroethyl)imidazo[1,2-c]pyrimidine in 2 ml of N,N-dimethylformamide, 57 mg of N-bromosuccinimide was added under ice cooling. After the addition was complete, the reaction mixture was stirred at room temperature for 2 hours. After completion of the reaction, 10 ml of water was added to the reaction mixture, and the mixture was extracted with diethyl ether (10 ml×2). The obtained organic layer was washed with a saturated aqueous solution of sodium thiosulfate and then with saturated sodium hydrogencarbonate in this order, dried and dried with saturated saline and then with anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. did. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient of 100:0 to 0:100) to obtain 127 mg of the desired product as a white solid.

Melting point: 200-205°C
¹ H-NMR(CDCl ₃ ): δ9.61(s, 1H), 9.20(s, 1H), 7.99(s, 1H), 7.96(d, J=9.6Hz, 1H), 7.68(d, J= 9.6Hz, 1H), 4.00(q, J=7.5Hz, 2H), 1.46(t, J=7.5Hz, 3H).
Synthesis Example 13: 2-[3-(ethylsulfonyl)-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-5-methyl-7-(perfluoroethyl)imidazo[1 , 2-c]Pyrimidine (Compound No. 1-3-007a of the present invention) 2-methyl-6-(perfluoroethyl)pyrimidin-4-amine (143 mg) was dissolved in bromobenzene (4 ml), and the mixture was allowed to stand at room temperature for 2 hours. 300 mg of -bromo-1-[3-(ethylsulfonyl)-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]ethanone were added. After the addition was completed, the reaction mixture was stirred with heating under reflux for 5 hours. After completion of the reaction, 10 ml of 1M sodium hydroxide aqueous solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate (10 ml×2). The obtained organic layer was dehydrated and dried over saturated saline and then anhydrous sodium sulfate in this order, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient 100:0 to 50:50) to obtain 82 mg of the desired product as a pale yellow solid. ..

Melting point: 224-226°C
¹ H-NMR(CDCl ₃ ): δ9.66(s, 1H), 8.46(s, 1H), 7.94(s, 1H), 7.90(d, J=9.6Hz, 1H), 7.66(dd, J= 9.6, 1.8Hz, 1H), 3.85(q, J=7.5Hz, 2H), 2.97(s, 3H), 1.37(t, J=7.5Hz, 3H).
Synthesis Example 14: 6-[3-(Ethylsulfonyl)-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-2-(trifluoromethyl)imidazo[2,1-b ] Synthesis of Thiazole (Compound of the Invention No. 1-12-001a) 106 mg of 5-(trifluoromethyl)thiazol-2-amine was dissolved in 4 ml of bromobenzene, and 2-bromo-1-[3- 300 mg of (ethylsulfonyl)-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]ethanone were added. After the addition was completed, the reaction mixture was stirred with heating under reflux for 5 hours. After completion of the reaction, 10 ml of 1M sodium hydroxide aqueous solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate (10 ml×2). The obtained organic layer was dehydrated and dried over saturated saline and then anhydrous sodium sulfate in this order, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient of 100:0 to 50:50) to obtain 153 mg of the desired product as a white solid.

Melting point: 219-220°C
¹ H-NMR(CDCl ₃ ): δ9.60(s, 1H), 8.44(s, 1H), 7.97-7.94(m, 1H), 7.87(d, J=9.6Hz, 1H), 7.62(dd, J=9.6, 1.5Hz, 1H), 3.59(q, J=7.5Hz, 2H), 1.30(t, J=7.5Hz, 3H).
Synthesis Example 15: 2-[3-(ethylthio)-1-methyl-5-(trifluoromethyl)-1H-indol-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[ 4,5-b]Pyridine (Compound No. 3-1-001b of the present invention) and 2-[3-(ethylsulfonyl)-1-methyl-5-(trifluoromethyl)-1H-indol-2-yl] Synthesis of 3--3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (Compound No. 3-1-001a of the present invention) Step 1: 1-Methyl-N-[2- (methylamino) -5- (trifluoromethyl) pyridin-3-yl] -5- (trifluoromethyl)-1H-indole-2-carboxylate synthesis of N ² amide - methyl-5- (trifluoromethyl) pyridine 573 mg of 2,3-diamine was dissolved in 10 ml of pyridine, and 608 mg of 1-methyl-5-(trifluoromethyl)-1H-indole-2-carboxylic acid and 1-ethyl-3-(3-dimethylamino) at room temperature. Propyl)carbodiimide hydrochloride 959 mg and 4-(dimethylamino)pyridine 31 mg were added. After the addition was complete, the reaction mixture was stirred at room temperature overnight. After completion of the reaction, 20 ml of water was added to the reaction mixture, and the precipitated solid was filtered off by filtration to obtain 1.02 g of the target product as a crude solid. This product was used as it was in the next step without further purification.

Step 2: 3-Methyl-2-[1-methyl-5-(trifluoromethyl)-1H-indol-2-yl]-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine Synthesis of crude 1-methyl-N-[2-(methylamino)-5-(trifluoromethyl)pyridin-3-yl]-5-(trifluoromethyl)-1H-indole obtained in step 1 968 mg of 2-carboxamide was dissolved in 10 ml of acetic acid, and the mixture was stirred with heating under reflux for 3 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. 10 ml of water was added to the obtained residue, and the mixture was extracted with ethyl acetate (10 ml×2). The obtained organic layer was dehydrated and dried over saturated saline and then anhydrous sodium sulfate in this order, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient of 100:0 to 0:100) to obtain 638 mg of the desired product as a skin-colored solid.

Melting point: 200-202°C
¹ H-NMR(DMSO-d6): δ8.84(d, J=1.4Hz, 1H), 8.64(d, J=1.4Hz, 1H), 8.15(s, 1H), 7.86(d, J=8.9 Hz, 1H), 7.63(dd, J=8.9, 1.4Hz, 1H), 7.46(s, 1H), 4.12(s, 3H), 4.06(s, 3H).
Step 3: 2-[3-iodo-1-methyl-5-(trifluoromethyl)-1H-indol-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5] -B] Synthesis of Pyridine 3-Methyl-2-[1-methyl-5-(trifluoromethyl)-1H-indol-2-yl]-6-(trifluoromethyl)-3H-imidazo[4,5- b] To a solution of 478 mg of pyridine and 8 ml of N,N-dimethylformamide, 405 mg of N-iodosuccinimide was added at room temperature. After the addition was completed, the reaction mixture was stirred with heating under reflux for 7 hours. After completion of the reaction, saturated aqueous sodium thiosulfate solution was added to the reaction mixture, and the precipitated solid was filtered off by filtration to obtain 675 mg of the desired product as a white solid.

Melting point: 165-167°C
¹ H-NMR(CDCl ₃ ): δ8.82(d, J=1.4Hz, 1H), 8.43(d, J=1.4Hz, 1H), 7.90-7.87(m, 1H), 7.66(dd, J= 8.7, 1.4Hz, 1H), 7.52(d, J=8.7Hz, 1H), 3.97(s, 3H), 3.85(s, 3H).
Step 4: 2-[3-(Ethylthio)-1-methyl-5-(trifluoromethyl)-1H-indol-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4 ,5-b]Pyridine (Compound No. 3-1-001b of the present invention) 2-[3-iodo-1-methyl-5-(trifluoromethyl)-1H-indol-2-yl]-3- A solution of 626 mg of methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine in 10 ml of 1,4-dioxane was added with 154 mg of diisopropylethylamine and 4,5'-bis(diphenylphosphino) at room temperature. )-9,9'-Dimethylxanthene 69 mg, tris(dibenzylideneacetone)dipalladium(0) 54 mg and ethanethiol 111 mg were sequentially added. After the addition was completed, the inside of the reaction vessel was replaced with nitrogen gas, and then the mixture was stirred under heating under reflux for 1.5 hours. After completion of the reaction, the reaction mixture was filtered through Celite and the Celite was washed with chloroform. The obtained filtrate and washing solution were combined, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient of 100:0 to 50:50) to obtain 545 mg of the desired product as a light yellow solid. ..

Melting point: 153-155°C
¹ H-NMR(CDCl ₃ ): δ8.80(s, 1H), 8.40(s, 1H), 8.19(s, 1H), 7.65(d, J=8.5Hz, 1H), 7.55(d, J= 8.5Hz, 1H), 3.95(s, 3H), 3.85(s, 3H), 2.59(q, J=7.4Hz, 2H), 1.00(t, J=7.4Hz, 3H).
Step 5: 2-[3-(ethylsulfonyl)-1-methyl-5-(trifluoromethyl)-1H-indol-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[ Synthesis of 4,5-b]pyridine (Compound No. 3-1-001a of the present invention) 2-[3-(ethylthio)-1-methyl-5-(trifluoromethyl)-1H-indol-2-yl] -3-Methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine In a solution of 250 mg of chloroform in 5 ml of chloroform, 65% by mass of meta-chloroperbenzoic acid (about 30% by mass) under ice cooling. 333 mg (including water) was added. After the addition was complete, the reaction mixture was stirred at room temperature for 2 hours. After completion of the reaction, saturated aqueous sodium thiosulfate solution was added to the reaction mixture, and the mixture was extracted with chloroform (10 ml). The obtained organic layer was washed with a 1 M aqueous sodium hydroxide solution, dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient of 100:0 to 0:100) to obtain 245 mg of the desired product as a white solid.

Melting point: 143-146°C
¹ H-NMR(CDCl ₃ ): δ8.83(s, 1H), 8.50(s, 1H), 8.40(d, =1.7Hz, 1H), 7.75(dd, J=8.5, 1.7Hz, 1H), 7.63(d, J=8.5Hz, 1H), 3.88(s, 3H), 3.73(s, 3H), 3.30-3.11(m, 2H), 1.27(t, J=7.2Hz, 3H).
Synthesis Example 16: 2-[3-(ethylthio)-5-(trifluoromethyl)benzo[b]thiophen-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5] -B]pyridine (invention compound No. 3-1-002b) and 2-[3-(ethylsulfonyl)-5-(trifluoromethyl)benzo[b]thiophen-2-yl]-3-methyl-6 Synthesis of -(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (inventive compound No. 3-1-002a) Step 1: N-[2-(methylamino)-5-(trifluoro methyl) pyridin-3-yl] -5- (trifluoromethyl) benzo [b] thiophene-2-carboxylate -amide N ² - methyl-5- (trifluoromethyl) pyridine-2,3-diamine 573mg pyridine It was dissolved in 10 ml, and at room temperature, 5-(trifluoromethyl)benzo[b]thiophene-2-carboxylic acid 615 mg, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride 959 mg and 4-(dimethylamino). ) 31 mg of pyridine was added. After the addition was complete, the reaction mixture was stirred at room temperature overnight. After completion of the reaction, 20 ml of water was added to the reaction mixture, and the precipitated solid was filtered off by filtration to obtain 939 mg of a target product as a gray solid. This product was used as it was in the next step without further purification.

Step 2: Synthesis of 3-methyl-6-(trifluoromethyl)-2-[5-(trifluoromethyl)benzo[b]thiophen-2-yl]-3H-imidazo[4,5-b]pyridine Step N-[2-(methylamino)-5-(trifluoromethyl)pyridin-3-yl]-5-(trifluoromethyl)benzo[b]thiophene-2-carboxamide 877 mg of the crude product obtained in 1. Was dissolved in 10 ml of acetic acid, and the mixture was stirred with heating under reflux for 3 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. 10 ml of water was added to the obtained residue, and the mixture was extracted with ethyl acetate (10 ml×2). The obtained organic layer was dehydrated and dried over saturated saline and then anhydrous sodium sulfate in this order, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient of 100:0 to 0:100) to obtain 683 mg of the desired product as a skin-colored solid.

Melting point: 191-193°C
¹ H-NMR(DMSO-d6): δ8.83-8.79(m, 1H), 8.62-8.59(m, 1H), 8.53(s, 1H), 8.44(s, 1H), 8.36(d, J= 8.5Hz, 1H), 7.80(d, J=8.5Hz, 1H), 4.24(s, 3H).
Step 3: 2-[3-chloro-5-(trifluoromethyl)benzo[b]thiophen-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]. Synthesis of Pyridine 3-Methyl-6-(trifluoromethyl)-2-[5-(trifluoromethyl)benzo[b]thiophen-2-yl]-3H-imidazo[4,5-b]pyridine 400 mg N To a solution of 5 ml of N,N-dimethylformamide was added 590 mg of 1,3-dichloro-5,5-dimethylhydantoin at 80°C. After the addition was complete, the reaction mixture was stirred at 80° C. for 1.5 hours. After completion of the reaction, saturated aqueous sodium thiosulfate solution was added to the reaction mixture, and the precipitated solid was filtered off by filtration to obtain 390 mg of the desired product as a white solid.

Melting point: 158-160°C
¹ H-NMR(CDCl ₃ ): δ8.81-8.77(m, 1H), 8.41-8.38(m, 1H), 8.29-8.26(m, 1H), 8.06(d, J=8.5Hz, 1H), 7.80(d, J=8.5Hz, 1H), 4.04(s, 3H).
Step 4: 2-[3-(ethylthio)-5-(trifluoromethyl)benzo[b]thiophen-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5- b] Synthesis of pyridine (invention compound No. 3-1-002b) 2-[3-chloro-5-(trifluoromethyl)benzo[b]thiophen-2-yl]-3-methyl-6-(tri To a solution of 370 mg of fluoromethyl)-3H-imidazo[4,5-b]pyridine in 5 ml of N,N-dimethylformamide, 119 mg of sodium ethanethiolate was added at 80°C. After the addition was complete, the reaction mixture was stirred at 80° C. for 1.5 hours. After completion of stirring, 159 mg of sodium ethanethiolate was added to the reaction mixture at 80°C. After completion of the reaction, 20 ml of water was added to the reaction mixture, and the mixture was extracted with ethyl acetate (20 ml×2). The obtained organic layer was dehydrated and dried over saturated saline and then anhydrous sodium sulfate in this order, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography eluting with n-hexane-ethyl acetate (gradient of 100:0 to 0:100) to obtain 186 mg of the desired product as a yellow solid.

Melting point: 120-122°C
¹ H-NMR(CDCl ₃ ): δ8.78(s, 1H), 8.41(s, 1H), 8.38(d, J=1.8Hz, 1H), 8.06(d, J=8.6Hz, 1H), 7.77 -7.74(m, 1H), 3.96(s, 3H), 2.69(q, J=7.4Hz, 2H), 1.05(t, J=7.4Hz, 3H).
Step 5: 2-[3-(ethylsulfonyl)-5-(trifluoromethyl)benzo[b]thiophen-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5] -B] Synthesis of pyridine (Compound No. 3-1-002a of the present invention) 2-[3-(ethylthio)-5-(trifluoromethyl)benzo[b]thiophen-2-yl]-3-methyl-6 To a solution of 147 mg of -(trifluoromethyl)-3H-imidazo[4,5-b]pyridine in 3 ml of chloroform was added 195 mg of 65 mass% metachloroperbenzoic acid (containing about 30 mass% water) under ice cooling. Was added. After the addition was complete, the reaction mixture was stirred at room temperature for 4 hours. After completion of the reaction, saturated aqueous sodium thiosulfate solution was added to the reaction mixture, and the mixture was extracted with chloroform (10 ml). The obtained organic layer was washed with a 1 M aqueous sodium hydroxide solution, dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient of 100:0 to 0:100) to obtain 104 mg of the desired product as a white solid.

Melting point: 70-75°C
¹ H-NMR(CDCl ₃ ): δ8.85(s, 1H), 8.79(d, J=1.5Hz, 1H), 8.35(d, J=1.8Hz, 1H), 8.13(d, J=8.6Hz , 1H), 7.85(dd, J=8.6, 1.8Hz, 1H), 3.89(s, 3H), 3.38(q, J=7.5Hz, 2H), 1.32(t, J=7.5Hz, 3H).
Synthesis Example 17: 2-[3-(Ethylthio)-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-6-(trifluoromethyl)-2H-pyrazolo[4,3 -B]pyridine (invention compound No. 1-10-002b) and 2-[3-(ethylsulfonyl)-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-6 Synthesis of -(trifluoromethyl)-2H-pyrazolo[4,3-b]pyridine (Compound No. 1-10-002a of the present invention) Step 1: 2-[3-(ethylthio)-7-(trifluoromethyl) ) Synthesis of imidazo[1,2-a]pyridin-2-yl]-6-(trifluoromethyl)-2H-pyrazolo[4,3-b]pyridine (present compound No. 1-10-002b) 3 A solution of 400 mg of -nitro-5-(trifluoromethyl)picolinaldehyde and 522 mg of 3-(ethylthio)-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-amine in 5 ml of xylene was heated under reflux. Stirred below for 1 hour. After completion of stirring, 1.50 g of triethyl phosphite was added to the reaction mixture at room temperature. After the addition was completed, the reaction mixture was stirred with heating under reflux for 1 hour. After completion of the reaction, the solvent was distilled off from the reaction mixture. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient of 100:0 to 50:50) to obtain 613 mg of the desired product as a pale yellow solid. ..

Melting point: 161-163°C
¹ H-NMR(CDCl ₃ ): δ9.43-9.41(m, 1H), 8.85(d, J=2.1Hz, 1H), 8.76(d, J=7.4Hz, 1H), 8.53-8.49(m, 1H), 8.05-8.00(m, 1H), 7.30-7.20(m, 1H), 2.99(q, J=7.5Hz, 2H), 1.21(t, J=7.5Hz, 3H).
Step 2: 2-[3-(ethylsulfonyl)-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-6-(trifluoromethyl)-2H-pyrazolo[4,3 -B] Synthesis of pyridine (invention compound No. 1-10-002a) 2-[3-(ethylthio)-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-6 To a solution of 150 mg of -(trifluoromethyl)-2H-pyrazolo[4,3-b]pyridine in 5 ml of chloroform was added 204 mg of metachloroperbenzoic acid (containing 35% by weight of water) under ice cooling. After the addition was complete, the reaction mixture was stirred at room temperature for 2 hours. After completion of stirring, 40 mg of metachloroperbenzoic acid (containing 35% by weight of water) was added to the reaction mixture at room temperature. After the addition was complete, the reaction mixture was stirred at room temperature for 2 hours. After completion of the reaction, 3 ml of saturated aqueous sodium thiosulfate solution was added to the reaction mixture, and the mixture was extracted with chloroform (10 ml×2). The obtained organic layer was washed with a 1 M aqueous sodium hydroxide solution, dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient of 100:0 to 0:100) to obtain 61 mg of the desired product as a white solid.

Melting point: 245-247°C
¹ H-NMR(CDCl ₃ ): δ9.44(d, J=7.2Hz, 1H), 9.17-9.15(m, 1H), 8.86(d, J=1.8Hz, 1H), 8.48-8.43(m, 1H), 8.13-8.09(m, 1H), 7.35-7.30(m, 1H), 4.04(q, J=7.5Hz, 2H), 1.48(t, J=7.5Hz, 3H).
Synthesis Example 18: 2-[3-(Ethylthio)-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-6-(trifluoromethyl)-2H-pyrazolo[4,3 -C]Pyridine (the present compound No. 1-11-001b) and 2-[3-(ethylsulfonyl)-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-6. Synthesis of -(trifluoromethyl)-2H-pyrazolo[4,3-c]pyridine (Compound No. 1-11-001a of the present invention) Step 1: Synthesis of 4-azido-6-(trifluoromethyl)nicotinaldehyde To a solution of 1.50 g of 4-chloro-6-(trifluoromethyl)nicotinaldehyde in 10 ml of N,N-dimethylformamide, 511 mg of sodium azide was added under ice cooling. After the addition was complete, the reaction mixture was stirred at room temperature for 3 hours. After completion of the reaction, 10 ml of water was added to the reaction mixture, and the mixture was extracted with diethyl ether (20 ml×2). The obtained organic layer was dehydrated and dried over saturated saline and then anhydrous sodium sulfate in this order, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography eluting with n-hexane-ethyl acetate (gradient of 100:0 to 80:20) to obtain 2.13 g of the desired product as a white solid.

Melting point: 54-56°C
¹ H-NMR(CDCl ₃ ): δ 10.39(s, 1H), 9.06(s, 1H), 7.54(s, 1H).
Step 2: 2-[3-(ethylthio)-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-6-(trifluoromethyl)-2H-pyrazolo[4,3- c] Synthesis of pyridine (invention compound No. 1-11-001b) 4-azido-6-(trifluoromethyl)nicotinaldehyde 200 mg and 3-(ethylthio)-7-(trifluoromethyl)imidazo[1,2] -A] To a solution of 266 mg of pyridin-2-amine in 5 ml of dichloromethane, 282 mg of triethylamine and 1 ml of 0.56 ml of 1M titanium(IV) chloride in dichloromethane were sequentially added under ice cooling. After the addition was complete, the reaction mixture was stirred at room temperature for 1 hour. After completion of the reaction, the solvent was distilled off from the reaction mixture under reduced pressure. The obtained residue was filtered through Celite, and Celite was washed with 20 ml of xylene. The obtained washing liquid was stirred under heating under reflux for 2 hours. After completion of the reaction, 10 ml of water was added to the reaction mixture, and the mixture was extracted with ethyl acetate (20 ml×2). The obtained organic layer was dehydrated and dried over saturated saline and then anhydrous sodium sulfate in this order, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography eluting with n-hexane-ethyl acetate (gradient of 100:0 to 50:50) to obtain 250 mg of the desired product as a pale yellow solid.

Melting point: 183-185°C
¹ H-NMR(CDCl ₃ ): δ9.40-9.37(m, 1H), 9.29(d, J=0.9Hz, 1H), 8.77(d, J=7.4Hz, 1H), 8.14(s, 1H) , 8.04-7.99(m, 1H), 7.30-7.25(m, 1H), 3.02(q, J=7.4Hz, 2H), 1.21(t, J=7.4Hz, 3H).
Step 3: 2-[3-(ethylsulfonyl)-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-6-(trifluoromethyl)-2H-pyrazolo[4,3 -C] Synthesis of pyridine (invention compound No. 1-11-001a) 2-[3-(ethylthio)-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-6 To a solution of 120 mg of -(trifluoromethyl)-2H-pyrazolo[4,3-c]pyridine in 5 ml of chloroform was added 164 mg of 65% by mass of metachloroperbenzoic acid (containing about 30% by mass of water) under ice cooling. Was added. After the addition was complete, the reaction mixture was stirred at room temperature overnight. After completion of the reaction, saturated aqueous sodium thiosulfate solution was added to the reaction mixture, and the mixture was extracted with chloroform (10 ml×2). The obtained organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution, dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient of 100:0 to 0:100) to obtain 63 mg of the desired product as a white solid.

Melting point: 230-233°C
¹ H-NMR(CDCl ₃ ): δ9.43(d, J=7.4Hz, 1H), 9.41-9.37(m, 1H), 9.07(s, 1H), 8.12-8.06(m, 2H), 7.36( dd, J=7.4, 1.8Hz, 1H), 4.03(q, J=7.4Hz, 2H), 1.48(t, J=7.4Hz, 3H).
Synthesis Example 19: 2-[3-(Ethylthio)-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-6-(trifluoromethyl)thiazolo[5,4-b] Pyridine (the present compound No. 1-13-001b) and 2-[3-(ethylsulfonyl)-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-6-(tri Synthesis of Fluoromethyl)thiazolo[5,4-b]pyridine (Compound No. 1-13-001a of the Present Invention) Step 1: 3-(Ethylthio)-N-[2-mercapto-5-(trifluoromethyl)pyridine Synthesis of -3-yl]-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-carboxamide 3-amino-5-(trifluoromethyl)pyridine-2-thiol 500 mg in pyridine 5 ml. Dissolve and at room temperature 3-(ethylthio)-7-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylic acid 621 mg, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride 820 mg salt and 10 mg 1-hydroxybenzotriazole were added. After the addition was complete, the reaction mixture was stirred at room temperature overnight. After completion of the reaction, water was added to the reaction mixture, and the precipitated solid was filtered off by filtration to obtain 234 mg of the desired product as a brown solid. This product was used as it was in the next step without further purification.

Step 2: 2-[3-(ethylthio)-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-6-(trifluoromethyl)thiazolo[5,4-b]pyridine Synthesis of (invention compound No. 1-13-001b) 3-(ethylthio)-N-[2-mercapto-5-(trifluoromethyl)pyridin-3-yl]-of the crude product obtained in Step 1 214 mg of 7-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxamide was dissolved in 5 ml of propionic acid, and the mixture was stirred with heating under reflux for 4 hours. After completion of stirring, the reaction mixture was stirred overnight at room temperature. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate (10 ml×2). The obtained organic layer was washed with a 1 M aqueous sodium hydroxide solution, dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by preparative medium pressure liquid chromatography under elution with n-hexane-ethyl acetate (gradient of 100:0 to 0:100) to obtain 20 mg of the desired product as a white solid.

Melting point: 150-160°C
¹ H-NMR(CDCl ₃ ): δ8.91-8.87(m, 1H), 8.71(d, J=7.5Hz, 1H), 8.65-8.61(m, 1H), 8.06(s, 1H), 7.20( dd, J=7.5, 1.5Hz, 1H), 3.08(q, J=7.4Hz, 2H), 1.27(t, J=7.4Hz, 3H).
Step 3: 2-[3-(ethylsulfonyl)-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-6-(trifluoromethyl)thiazolo[5,4-b] Synthesis of pyridine (invention compound No. 1-13-001a) 2-[3-(ethylthio)-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-6-(tri To a solution of 20 mg of fluoromethyl)thiazolo[5,4-b]pyridine in 3 ml of chloroform, 27 mg of 65% by mass of metachloroperbenzoic acid (containing about 30% by mass of water) was added under ice cooling. After the addition was complete, the reaction mixture was stirred at room temperature for 2 hours. After completion of the reaction, saturated aqueous sodium thiosulfate solution was added to the reaction mixture, and the mixture was extracted with chloroform (10 ml×2). The obtained organic layer was washed with a 1 M aqueous sodium hydroxide solution, dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient 100:0 to 50:50) to obtain 15 mg of the desired product as a white solid.

Melting point: 243-245°C
¹ H-NMR(CDCl ₃ ): δ9.53(d, J=7.5Hz, 1H), 8.95-8.93(m, 1H), 8.63-8.61(m, 1H), 8.17-8.14(m, 1H), 7.30(dd, J=7.5, 1.9Hz, 1H), 4.10(q, J=7.5Hz, 2H), 1.45(t, J=7.5Hz, 3H).
Synthesis Example 20: 2-[3-(ethylthio)-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-6-iodo-3-methyl-3H-imidazo[4,5] -B] pyridine (the present compound No. 1-1-026b), 2-ethylhexyl 3-((2-(3-(ethylthio)-7-(trifluoromethyl)imidazo[1,2-a] Pyridin-2-yl)-3-methyl-3H-imidazo[4,5-b]pyridin-6-yl)thio)propanoate (present compound No. 1-1-028b), 2-[3-(ethylthio )-7-(Trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6-((trifluoromethyl)thio)-3H-imidazo[4,5-b]pyridine (Inventive compound No. 1-1-027b) and 2-[3-(ethylsulfonyl)-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6. Synthesis of -((trifluoromethyl)thio)-3H-imidazo[4,5-b]pyridine (Compound No. 1-1-027a of the present invention) Step 1: 3-(Ethylthio)-N-[5-iodo 2- (methylamino) pyridin-3-yl] -7- (trifluoromethyl) imidazo [1,2-a] pyridine-2-carboxylate the synthesis of amide 5-iodo -N ² - methylpyridine-2,3 -1.59 g of diamine was dissolved in 15 ml of pyridine, and at room temperature 1.54 g of 3-(ethylthio)-7-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylic acid and 1-ethyl- 2.45 g of 3-(3-dimethylaminopropyl)carbodiimide hydrochloride was added. After the addition was complete, the reaction mixture was stirred at room temperature overnight. After completion of the reaction, water was added to the reaction mixture, and the precipitated solid was filtered off by filtration to obtain 2.49 g of the target product as a gray solid. This product was used as it was in the next step without further purification.

¹ H-NMR(CDCl ₃ ): δ8.97(brs, 1H), 8.71(d, J=7.2Hz, 1H), 8.27(d, J=2.0Hz, 1H), 8.07(d, J=2.0Hz , 1H), 7.96(s, 1H), 7.19(dd, J=7.2, 2.0Hz, 1H), 4.78(brs, 1H), 3.08(q, J=7.4Hz, 2H), 3.03(d, J= 4.8Hz, 3H), 1.22(t, J=7.4Hz, 3H).
Step 2: 2-[3-(ethylthio)-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-6-iodo-3-methyl-3H-imidazo[4,5- b] Synthesis of pyridine (invention compound No. 1-1-026b) 3-(ethylthio)-N-[5-iodo-2-(methylamino)pyridin-3-yl of the crude product obtained in Step 1 ]-7-(Trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxamide (2.49 g) was dissolved in acetic acid (15 ml), and the mixture was stirred with heating under reflux for 3.5 hr. After the reaction was completed, water was added to the reaction mixture, and the precipitated solid was filtered off by filtration. The obtained solid was washed with n-hexane to obtain 2.02 g of the desired product as a brown solid.

Melting point: 230-233°C
¹ H-NMR(CDCl ₃ ): δ8.76(d, J=7.2Hz, 1H), 8.62(d, J=1.7Hz, 1H), 8.47(d, J=1.7Hz, 1H), 8.03(s , 1H), 7.19(dd, J=7.2, 1.7Hz, 1H), 4.25(s, 3H), 3.11(q, J=7.5Hz, 2H), 1.20(t, J=7.5Hz, 3H).
Step 3: 2-Ethylhexyl 3-((2-(3-(ethylthio)-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl)-3-methyl-3H-imidazo Synthesis of [4,5-b]pyridin-6-yl)thio)propanoate (Compound No. 1-1-028b of the present invention) 2-[3-(ethylthio)-7-(trifluoromethyl)imidazo[1, To a solution of 503 mg of 2-a]pyridin-2-yl]-6-iodo-3-methyl-3H-imidazo[4,5-b]pyridine in 10 ml of 1,4-dioxane was added 387 mg of diisopropylethylamine at room temperature, 4 58 mg of 5,5'-bis(diphenylphosphino)-9,9'-dimethylxanthene, 92 mg of tris(dibenzylideneacetone)dipalladium(0) and 262 mg of 2-ethylhexyl 3-mercaptopropionate were sequentially added. After the addition was completed, the inside of the reaction vessel was replaced with nitrogen gas, and then the mixture was stirred under heating under reflux for 4 hours. After completion of the reaction, 10 ml of water was added to the reaction mixture, and the mixture was extracted with diethyl ether (10 ml×2). The obtained organic layer was dehydrated and dried over saturated saline and then anhydrous sodium sulfate in this order, and the solvent was distilled off under reduced pressure. The obtained residue was purified by preparative medium pressure liquid chromatography under elution with n-hexane-ethyl acetate (gradient of 100:0 to 80:20) to obtain 599 mg of the desired product as a yellow solid.

Melting point: 94-96°C
¹ H-NMR(CDCl ₃ ): δ8.76(d, J=7.2Hz, 1H), 8.53(d, J=2.0Hz, 1H), 8.27(d, J=2.0Hz, 1H), 8.03(s , 1H), 7.18(dd, J=7.2, 1.9Hz, 1H), 4.27(s, 3H), 4.01(dd, J=5.8, 1.7Hz, 2H), 3.20-3.05(m, 4H), 2.62( t, J=7.3Hz, 2H), 1.45-1.20(m, 12H), 0.89(t, J=7.5Hz, 6H).
Step 4: 2-[3-(ethylthio)-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6-((trifluoromethyl)thio)-3H. -Synthesis of imidazo[4,5-b]pyridine (Compound No. 1-1-027b of the present invention) 2-ethylhexyl 3-((2-(3-(ethylthio)-7-(tri Fluoromethyl)imidazo[1,2-a]pyridin-2-yl)-3-methyl-3H-imidazo[4,5-b]pyridin-6-yl)thio)propanoate 560 mg of tetrahydrofuran in 5 ml of tetrahydrofuran was ice-cooled. 159 mg of potassium tert-butoxide was added underneath. After the addition was completed, the reaction mixture was stirred under ice cooling for 30 minutes. After completion of stirring, 756 mg of S-(trifluoromethyl)dibenzothiophenium trifluoromethanesulfonate was added to the reaction mixture under ice cooling. After the addition was complete, the reaction mixture was stirred at room temperature overnight. After completion of the reaction, water was added to the reaction mixture and extracted with chloroform (10 ml×2). The obtained organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution, dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by thin layer chromatography eluting with n-hexane-ethyl acetate (gradient 100:0 to 80:20) to obtain 69 mg of the desired product as a pale yellow solid.

Melting point: 209-210°C
¹ H-NMR(CDCl ₃ ): δ8.77(d, J=7.2Hz, 1H), 8.66(d, J=2.0Hz, 1H), 8.46(d, J=2.0Hz, 1H), 8.05-8.02 (m, 1H), 7.20(dd, J=7.2, 1.9Hz, 1H), 4.31(s, 3H), 3.14(q, J=7.4Hz, 2H), 1.21(t, J=7.4Hz, 3H) .
Step 5: 2-[3-(ethylsulfonyl)-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6-((trifluoromethyl)thio)- Synthesis of 3H-imidazo[4,5-b]pyridine (Compound No. 1-1-027a of the present invention) 2-[3-(ethylthio)-7-(trifluoromethyl)imidazo[1,2-a]pyridine 2-yl]-3-methyl-6-((trifluoromethyl)thio)-3H-imidazo[4,5-b]pyridine (31 mg) was added to a solution of chloroform (3 ml) under ice-cooling in an amount of 65 mass% metachloroperoxide. 38 mg of benzoic acid (containing about 30% by weight of water) were added. After the addition was complete, the reaction mixture was stirred at room temperature for 2 hours. After completion of the reaction, saturated aqueous sodium thiosulfate solution was added to the reaction mixture, and the mixture was extracted with chloroform (10 ml×2). The obtained organic layer was washed with a 1 M aqueous sodium hydroxide solution, dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient of 100:0 to 50:50) to obtain 34 mg of the desired product as a white solid.

Melting point: 220-223°C
¹ H-NMR(CDCl ₃ ): δ9.41(d, J=7.4Hz, 1H), 8.70(d, J=2.0Hz, 1H), 8.41(dJ=2.0Hz, 1H), 8.14(s, 1H ), 7.31(dd, J=7.4, 1.6Hz, 1H), 4.16(s, 3H), 4.11(q, J=7.4Hz, 2H), 1.45(t, J=7.4Hz, 3H).
Synthesis Example 21: 2-[3-(ethylsulfonyl)-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H- Synthesis of imidazo[4,5-b]pyridine 4-oxide (inventive compound No. 1-14-001a) 2-[3-(ethylsulfonyl)-7-(trifluoromethyl)imidazo[1,2-a ]Pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine in a solution of 500 mg in 15 ml of acetonitrile under ice cooling, 65% by mass of metachloroperbenzoic acid 834 mg of acid (containing about 30% by weight of water) was added. After the addition was complete, the reaction mixture was stirred at 50° C. for 20 hours. After the completion of stirring, 279 mg of 65 mass% metachloroperbenzoic acid (containing about 30 mass% water) was added to the reaction mixture at room temperature. After the addition was complete, the reaction mixture was stirred at 50° C. for 20 hours. After completion of stirring, 418 mg of 65 mass% metachloroperbenzoic acid (containing about 30 mass% water) was added to the reaction mixture at room temperature. After the addition was complete, the reaction mixture was stirred at 50° C. for 20 hours. After completion of the reaction, saturated sodium thiosulfate aqueous solution was added to the reaction mixture, and the mixture was extracted with chloroform (20 ml×2). The obtained organic layer was washed with a 1 M aqueous sodium hydroxide solution, dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient of 100:0 to 0:100) to obtain 67 mg of the desired product as a white solid.

¹ H-NMR(CDCl ₃ ): δ9.35(d, J=7.2Hz, 1H), 8.48-8.46(m, 1H), 8.19-8.16(m, 1H), 7.96(s, 1H), 7.35( dd, J=7.2, 1.7Hz, 1H), 4.58(s, 3H), 3.94(q, J=7.4Hz, 2H), 1.46(t, J=7.4Hz, 3H).
Synthesis Example 22: 8-[3-(Ethylthio)-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-9-methyl-(trifluoromethyl)-9H-imidazo[4 , 5-c] Pyridazine (inventive compound No. 1-16-001b) and 8-[3-(ethylsulfonyl)-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl] Synthesis of -9-methyl-(trifluoromethyl)-9H-imidazo[4,5-c]pyridazine (inventive compound No. 1-16-001a) Step 1: 3-(ethylthio)-N-[3- Synthesis of (methylamino)-6-(trifluoromethyl)pyridazin-4-yl]-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxamide 4-bromo-N-methyl- 6-(Trifluoromethyl)pyridazin-3-amine 300 mg, 3-(ethylthio)-6-(trifluoromethyl)imidazo[1,2-a]pyridine-carboxamide 509 mg, potassium phosphate 497 mg and N,N'. -52 mg of dimethylethylenediamine was dissolved in 4 ml of N,N-dimethylformamide, and 56 mg of copper(I) iodide was added at room temperature. After the addition was completed, the inside of the reaction vessel was replaced with nitrogen gas, and then the mixture was stirred at 90° C. for 9 hours. After completion of the reaction, 10 ml of water was added to the reaction mixture, and the mixture was extracted with ethyl acetate (10 ml×2). The obtained organic layer was dehydrated and dried over saturated saline and then anhydrous sodium sulfate in this order, and then the solvent was distilled off under reduced pressure to obtain the desired product, 3-(ethylthio)-N-[3-(methylamino). )-6-(Trifluoromethyl)pyridazin-4-yl]-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxamide crude product was obtained. This product was directly used in the next step without further purification.

Step 2: 8-[3-(ethylthio)-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-9-methyl-(trifluoromethyl)-9H-imidazo[4. Synthesis of 5-c]pyridazine (Compound No. 1-16-001b of the present invention) Crude 3-(ethylthio)-N-[3-(methylamino)-6-(trifluoromethyl) obtained in Step 1 ) Pyridazin-4-yl]-7-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxamide was dissolved in 10 ml of acetic acid, and the mixture was stirred with heating under reflux for 7 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. 10 ml of water was added to the obtained residue, and the mixture was extracted with ethyl acetate (10 ml×2). The obtained organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and 28% by mass aqueous ammonia in this order, dehydrated and dried over saturated brine and then anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. After dehydration and drying in order of saturated saline 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 (gradient of 100:0 to 25:75) to obtain 72 mg of the desired product as a pale yellow solid. ..

Melting point: 240-242°C
¹ H-NMR(CDCl ₃ ): δ9.05-9.00(m, 1H), 8.23(s, 1H), 7.85(d, J=9.8Hz, 1H), 7.56(dd, J=9.4, 1.6Hz, 1H), 4.55(s, 3H), 3.16(q, J=7.4Hz, 2H), 1.25(t, J=7.4Hz, 3H).
Step 3: 8-[3-(ethylsulfonyl)-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-9-methyl-(trifluoromethyl)-9H-imidazo[4 ,5-c]Pyridazine (Compound No. 1-16-001a of the present invention) 8-[3-(ethylthio)-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl] To a solution of 62 mg of -9-methyl-(trifluoromethyl)-9H-imidazo[4,5-c]pyridazine in 5 ml of chloroform was added 65% by mass of metachloroperbenzoic acid (about 30% by mass of water under ice cooling). 81 mg) was added. After the addition was complete, the reaction mixture was stirred at room temperature for 1 hour. After completion of the reaction, saturated aqueous sodium thiosulfate solution was added to the reaction mixture, and the mixture was extracted with chloroform (10 ml). The obtained organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution, dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient of 100:0 to 25:75) to obtain 66 mg of the desired product as a light yellow solid. ..

Melting point: 274-276°C
¹ H-NMR(CDCl ₃ ): δ9.70-9.60(m, 1H), 8.22(s, 1H), 7.99(d, J=9.4Hz, 1H), 7.75(dd, J=9.4, 1.6Hz, 1H), 4.38(s, 3H), 4.05(q, J=7.4Hz, 2H), 1.48(t, J=7.4Hz, 3H).
Synthesis Example 23: 2-[3-(Ethylthio)-6-(trifluoromethyl)imidazo[1,2-a]pyrimidin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo [4,5-b]Pyridine (the present compound No. 1-1-054b) and 2-[3-(ethylsulfonyl)-6-(trifluoromethyl)imidazo[1,2-a]pyrimidine-2- [Ill]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (invention compound No. 1-1-054a) Step 1: 3-methyl-6-( Synthesis of trifluoromethyl)-2-[6-(trifluoromethyl)imidazo[1,2-a]pyrimidin-2-yl]-3H-imidazo[4,5-b]pyridine 5-(trifluoromethyl) 250 mg of pyrimidin-2-amine was dissolved in 10 ml of acetonitrile, and 2-bromo-1-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine-2- was dissolved at room temperature. Ill]ethanone 550 mg was added. After the addition was completed, the reaction mixture was stirred with heating under reflux for 7.5 hours. After completion of the reaction, 10 ml of water was added to the reaction mixture, and the precipitated solid was filtered off by filtration to obtain 445 mg of the desired product as a yellow solid.

Melting point: 283-285°C
¹ H-NMR(CDCl ₃ ): δ8.92-8.89(m, 1H), 8.84(d, J=2.4Hz, 1H), 8.73(s, 1H), 8.57(s, 1H), 8.29(s, 1H), 4.53(s, 3H).
Step 2: 2-[3-iodo-6-(trifluoromethyl)imidazo[1,2-a]pyrimidin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4. Synthesis of 5-b]pyridine 3-methyl-6-(trifluoromethyl)-2-[6-(trifluoromethyl)imidazo[1,2-a]pyrimidin-2-yl]-3H-imidazo[4. To a solution of 415 mg of 5-b]pyridine in 4 ml of N,N-dimethylformamide, 408 mg of 1,3-diiodo-5,5-dimethylhydantoin was added at 80°C. After the addition was complete, the reaction mixture was stirred at 80° C. for 3 hours. After completion of the reaction, saturated aqueous sodium thiosulfate solution was added to the reaction mixture, and the precipitated solid was filtered off by filtration to obtain 468 mg of the desired product as a yellow solid.

Melting point: 260-265°C
¹ H-NMR(CDCl ₃ ): δ9.00-8.86(m, 1H), 8.81(d, J=2.4Hz, 1H), 8.74(d, J=1.5Hz, 1H), 8.42(d, J= 1.5Hz, 1H), 4.43(s, 3H).
Step 3: 2-[3-(ethylthio)-6-(trifluoromethyl)imidazo[1,2-a]pyrimidin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[ Synthesis of 4,5-b]pyridine (Compound No. 1-1-054b of the present invention) 2-[3-iodo-6-(trifluoromethyl)imidazo[1,2-a]pyrimidin-2-yl]- To a solution of 438 mg of 3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine in 10 ml of 1,4-dioxane, 334 mg of diisopropylethylamine and 4,5'-bis(diphenyl) were added at room temperature. 50 mg of phosphino)-9,9'-dimethylxanthene, 39 mg of tris(dibenzylideneacetone)dipalladium(0) and 106 mg of ethanethiol were sequentially added. After the addition was completed, the inside of the reaction vessel was replaced with nitrogen gas, and then the mixture was stirred under heating under reflux for 3 hours. After the reaction was completed, water was added to the reaction mixture, and the precipitated solid was filtered off by filtration. The obtained solid was washed with diisopropyl ether to obtain the desired product (337 mg) as a yellow solid.

Melting point: 220-222°C
¹ H-NMR(CDCl ₃ ): δ9.27-9.23(m, 1H), 8.88(d, J=2.1Hz, 1H), 8.75(s, 1H), 8.42(s, 1H), 4.42(s, 3H), 3.25(q, J=7.5Hz, 2H), 1.26(t, J=7.5Hz, 3H).
Step 4: 2-[3-(ethylsulfonyl)-6-(trifluoromethyl)imidazo[1,2-a]pyrimidin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo Synthesis of [4,5-b]pyridine (Compound No. 1-1-054a of the present invention) 2-[3-(ethylthio)-6-(trifluoromethyl)imidazo[1,2-a]pyrimidine-2- Yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine in a solution of 297 mg of chloroform in 7 ml of chloroform under ice cooling, 65% by weight of metachloroperbenzoic acid (about 30% by weight). % Water) 371 mg. After the addition was complete, the reaction mixture was stirred at room temperature for 3.5 hours. After completion of stirring, 100 mg of metachloroperbenzoic acid (containing 35% by weight of water) was added to the reaction mixture at room temperature. After the addition was complete, the reaction mixture was stirred at room temperature for 1 hour. After completion of stirring, 50 mg of metachloroperbenzoic acid (containing 35% by weight of water) was added to the reaction mixture at room temperature. After the addition was complete, the reaction mixture was stirred at room temperature for 1 hour. After completion of the reaction, saturated aqueous sodium thiosulfate solution was added to the reaction mixture, and the mixture was extracted with chloroform (10 ml×2). The obtained organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution, dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient 100:0 to 50:50) to obtain 150 mg of the desired product as a white solid.

Melting point: 244-248°C
¹ H-NMR(CDCl ₃ ): δ10.00-9.95(m, 1H), 9.04(d, J=2.4Hz, 1H), 8.80(s, 1H), 8.41-8.37(m, 1H), 4.30( s, 3H), 4.27(q, J=7.5Hz, 2H), 1.49(t, J=7.5Hz, 3H).
Synthesis Example 24: 2-[3-(Ethylthio)-7-(trifluoromethyl)imidazo[1,2-c]pyrimidin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo [4,5-b]Pyridine (Compound No. 1-1-055b of the present invention) and 2-[3-(ethylsulfonyl)-7-(trifluoromethyl)imidazo[1,2-c]pyrimidine-2- [Ill]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (Compound No. 1-1-055a of the present invention) Step 1: 3-Methyl-6-( Synthesis of trifluoromethyl)-2-[7-(trifluoromethyl)imidazo[1,2-c]pyrimidin-2-yl]-3H-imidazo[4,5-b]pyridine 6-(trifluoromethyl) 251 mg of pyrimidin-4-amine was dissolved in 10 ml of acetonitrile, and 2-bromo-1-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine-2- was dissolved at room temperature. Ill]ethanone 550 mg was added. After the addition was completed, the reaction mixture was stirred with heating under reflux for 7.5 hours. After completion of the reaction, 10 ml of water was added to the reaction mixture, and the precipitated solid was filtered off by filtration to obtain 335 mg of the desired product as a yellow solid.

Melting point: 257-260°C
¹ H-NMR(CDCl ₃ ): δ9.22(s, 1H), 8.73(d, J=1.2Hz, 1H), 8.64(s, 1H), 8.29(d, J=1.8Hz, 1H), 8.05 (s, 1H), 4.47(s, 3H).
Step 2: 2-[3-Bromo-7-(trifluoromethyl)imidazo[1,2-c]pyrimidin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4. Synthesis of 5-b]pyridine 3-Methyl-6-(trifluoromethyl)-2-[7-(trifluoromethyl)imidazo[1,2-c]pyrimidin-2-yl]-3H-imidazo[4. To a solution of 300 mg of 5-b]pyridine in 5 ml of N,N-dimethylformamide, 244 mg of 1,3-dibromo-5,5-dimethylhydantoin was added at 80°C. After the addition was complete, the reaction mixture was stirred at 80° C. for 30 minutes. After completion of the reaction, saturated sodium thiosulfate aqueous solution was added to the reaction mixture, and the precipitated solid was filtered off by filtration to obtain 468 mg of a target product as a yellow solid. This product was used as it was in the next step without further purification.

¹ H-NMR(CDCl ₃ ): δ9.27(s, 1H), 8.75(d, J=0.9Hz, 1H), 8.43(d, J=1.5Hz, 1H), 8.02(s, 1H), 4.37 (s, 3H).
Step 3: 2-[3-(ethylthio)-7-(trifluoromethyl)imidazo[1,2-c]pyrimidin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[ Synthesis of 4,5-b]pyridine (Compound No. 1-1-055b of the present invention) The crude 2-[3-bromo-7-(trifluoromethyl)imidazo[1,2- c]Pyrimidin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine To a solution of 452 mg of 1,4-dioxane in 10 ml of diisopropylethylamine 377 mg at room temperature. , 4,5'-bis(diphenylphosphino)-9,9'-dimethylxanthene (56 mg), tris(dibenzylideneacetone)dipalladium(0) (44 mg) and ethanethiol (121 mg) were sequentially added. After the addition was completed, the inside of the reaction vessel was replaced with nitrogen gas, and the mixture was stirred under heating under reflux for 6.5 hours. After completion of stirring, the reaction mixture was added with 754 mg of diisopropylethylamine, 112 mg of 4,5'-bis(diphenylphosphino)-9,9'-dimethylxanthene, 88 mg of tris(dibenzylideneacetone)dipalladium (0) at room temperature, and 242 mg of ethanethiol was added sequentially. After the addition was completed, the inside of the reaction vessel was replaced with nitrogen gas, and then the mixture was stirred under heating under reflux for 5 hours. After the reaction was completed, water was added to the reaction mixture, and the precipitated solid was filtered off by filtration. The obtained solid was washed with diisopropyl ether to obtain the desired product (371 mg) as a brown solid.

Melting point: 198-200°C
¹ H-NMR(CDCl ₃ ): δ9.54(s, 1H), 8.77-8.73(m, 1H), 8.41(s, 1H), 8.01(s, 1H), 4.32(s, 3H), 3.24( q, J=7.5Hz, 2H), 1.26(t, J=7.5Hz, 3H).
Step 4: 2-[3-(ethylsulfonyl)-7-(trifluoromethyl)imidazo[1,2-c]pyrimidin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo Synthesis of [4,5-b]pyridine (Compound of the present invention No. 1-1-055a) 2-[3-(ethylthio)-7-(trifluoromethyl)imidazo[1,2- A solution of 315 mg of c]pyrimidin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine in 10 ml of chloroform was mixed with 65% by mass of metachloroperoxide under ice cooling. Benzoic acid (containing about 30% by weight of water) 412 mg was added. After the addition was complete, the reaction mixture was stirred at room temperature for 3 hours. After completion of stirring, 206 mg of metachloroperbenzoic acid (containing 35% by weight of water) was added to the reaction mixture at room temperature. After the addition was complete, the reaction mixture was stirred at room temperature for 2 hours. After completion of the reaction, saturated aqueous sodium thiosulfate solution was added to the reaction mixture, and the mixture was extracted with chloroform (10 ml×2). The obtained organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution, dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by preparative medium pressure liquid chromatography under elution with n-hexane-ethyl acetate (gradient of 100:0 to 50:50) to obtain 139 mg of the desired product as a white solid.

Melting point: 238-240°C
¹ H-NMR(CDCl ₃ ): δ 10.15(s, 1H), 8.80(s, 1H), 8.39(s, 1H), 8.15(s, 1H), 4.22(s, 3H), 4.22(q, J=7.5Hz, 2H), 1.50(t, J=7.5Hz, 3H).
Synthesis Example 25: 2-[3-(ethylsulfonyl)-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-6-(trifluoromethyl)imidazo[1,2-a ] Synthesis of Pyrazine (Compound of the Invention No. 1-6-002a) 103 mg of 5-(trifluoromethyl)pyrazin-2-amine was dissolved in 4 ml of bromobenzene, and 2-bromo-1-[3 300 mg of -(ethylsulfonyl)-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]ethanone were added. After the addition was completed, the reaction mixture was stirred with heating under reflux for 5 hours. After completion of the reaction, 10 ml of 1M sodium hydroxide aqueous solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate (10 ml×2). The obtained organic layer was dehydrated and dried over saturated saline and then anhydrous sodium sulfate in this order, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient of 100:0 to 0:100) to obtain 38 mg of the desired product as a white solid.

Melting point: 266-270°C
¹ H-NMR(CDCl ₃ ): δ9.63(s, 1H), 9.24(s, 1H), 8.68(s, 1H), 8.62(s, 1H), 7.93(d, J=9.3Hz, 1H) , 7.66(dd, J=9.3, 1.8Hz, 1H), 3.70(q, J=7.5Hz, 2H), 1.35(t, J=7.5Hz, 3H).
Synthesis Example 26: 2-[7-Chloro-3-(ethylthio)imidazo[1,2-a]pyridin-2-yl]-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine (Invention compound No. 1-8-012b), 2-[7-chloro-3-(ethylthio)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl )-3H-imidazo[4,5-c]pyridine (invention compound No. 1-8-006b) and 2-[7-chloro-3-(ethylthio)imidazo[1,2-a]pyridine-2-) Iyl]-1-methyl-6-(trifluoromethyl)-1H-imidazo[4,5-c]pyridine (inventive compound No. 1-9-003b) Step 1: N-[5-amino- Synthesis of 2-(trifluoromethyl)pyridin-4-yl]-7-chloro-3-(ethylthio)imidazo[1,2-a]pyridine-2-carboxamide 6-(trifluoromethyl)pyridine-3, 470 mg of 4-diamine was dissolved in 7 ml of pyridine, and at room temperature, 486 mg of 7-chloro-3-(ethylthio)imidazo[1,2-a]pyridine-2-carboxylic acid and 1-ethyl-3-(3-dimethylamino). 752 mg of propyl)carbodiimide hydrochloride was added. After the addition was complete, the reaction mixture was stirred at room temperature overnight. After completion of the reaction, 20 ml of water was added to the reaction mixture, and the precipitated solid was filtered off by filtration to obtain 749 mg of the target product as a yellow solid. This product was used as it was in the next step without further purification.

Step 2: 2-[7-chloro-3-(ethylthio)imidazo[1,2-a]pyridin-2-yl]-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine( Synthesis of compound of the present invention No. 1-8-012b) N-[5-amino-2-(trifluoromethyl)pyridin-4-yl]-7-chloro-3-() of the crude product obtained in Step 1 749 mg of ethylthio)imidazo[1,2-a]pyridine-2-carboxamide was dissolved in 7 ml of propionic acid, and the mixture was stirred with heating under reflux for 20 hours. After completion of stirring, the solid precipitated in the reaction mixture was filtered off by filtration. The obtained solid was washed with water to obtain 761 mg of the desired product as a brown solid. This product was directly used in the next step without further purification.

Step 3: 2-[7-chloro-3-(ethylthio)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5- c]pyridine (invention compound No. 1-8-006b) and 2-[7-chloro-3-(ethylthio)imidazo[1,2-a]pyridin-2-yl]-1-methyl-6-( Synthesis of synthesis of trifluoromethyl)-1H-imidazo[4,5-c]pyridine (inventive compound No. 1-9-003b) 63 wt% sodium hydride (dispersed in mineral oil) 219 mg N,N- 2-[7-chloro-3-(ethylthio)imidazo[1,2-a]pyridin-2-yl]-6-(trifluoromethyl)-3H-imidazo[ was added to a solution of 10 ml of dimethylformamide under ice cooling. A solution of 761 mg of 4,5-c]pyridine in 10 ml of N,N-dimethylformamide was added. After the addition was completed, the reaction mixture was stirred under ice cooling for 30 minutes. After completion of stirring, 940 mg of methyl trifluoromethanesulfonate was added to the reaction mixture under ice cooling. After the addition was complete, the reaction mixture was stirred at room temperature for 1 hour. After completion of the reaction, 20 ml of water was added to the reaction mixture, and the mixture was extracted with diethyl ether (20 ml×2). The obtained organic layer was dehydrated and dried over saturated saline and then anhydrous sodium sulfate in this order, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient of 100:0 to 50:50) to give the desired product, 2-[7-chloro]. 65 mg of -3-(ethylthio)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine and the desired product. 2-[7-chloro-3-(ethylthio)imidazo[1,2-a]pyridin-2-yl]-1-methyl-6-(trifluoromethyl)-1H-imidazo[4,5-c]pyridine 247 mg each was obtained as a white solid.

2-[7-chloro-3-(ethylthio)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine Melting point: 215-217°C
¹ H-NMR(CDCl ₃ ): δ8.95(s, 1H), 8.59(d, J=7.5Hz, 1H), 8.19(s, 1H), 7.74-7.71(m, 1H), 7.03(dd, J=7.5, 2.1Hz, 1H), 4.33(s, 3H), 3.09(q, J=7.5Hz, 2H), 1.19(t, J=7.5Hz, 3H).
2-[7-chloro-3-(ethylthio)imidazo[1,2-a]pyridin-2-yl]-1-methyl-6-(trifluoromethyl)-1H-imidazo[4,5-c]pyridine Melting point: 187-188°C
¹ H-NMR(CDCl ₃ ): δ9.24(s, 1H), 8.59(dd, J=7.2, 0.6Hz, 1H), 7.81(s, 1H), 7.73-7.69(m, 1H), 7.03( dd, J=7.2, 1.8Hz, 1H), 4.26(s, 3H), 3.10(q, J=7.5Hz, 2H), 1.20(t, J=7.5Hz, 3H).
Synthesis Example 27: 2-[3-(Ethylthio)-6-iodo-8-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl) Synthesis of -3H-imidazo[4,5-b]pyridine (Compound No. 1-1-066b of the present invention) Step 1: 2-(ethylthio)-1-[3-methyl-6-(trifluoromethyl)- Synthesis of 3H-imidazo[4,5-b]pyridin-2-yl]ethanone 2-Bromo-1-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine- To an 80 ml solution of 20 g of 2-yl]ethanone in 80 ml of N,N-dimethylformamide, 4.2 g of ethanethiol and 9.4 g of potassium carbonate were sequentially added under ice cooling. After the addition was completed, the reaction mixture was stirred under ice cooling for 30 minutes. After completion of stirring, the reaction mixture was stirred at room temperature for 1 hour. After the reaction was completed, 100 ml of water was added to the reaction mixture, and the mixture was extracted with ethyl acetate (100 ml×2). The obtained organic layer was dehydrated and dried over saturated saline and then anhydrous sodium sulfate in this order, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient of 100:0 to 80:20) to obtain 13.8 g of the desired product as a light yellow solid. Obtained.

Melting point: 67-69°C
¹ H-NMR(CDCl ₃ ): δ8.85-8.80(m, 1H), 8.45-8.40(m, 1H), 4.24(s, 3H), 4.07(s, 2H), 2.66(q, J=7.4 Hz, 2H), 1.31(t, J=7.4Hz, 3H).
Step 2: Synthesis of 2-bromo-2-(ethylthio)-1-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl]ethanone 2-( 3. Ethylthio)-1-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl]ethanone (11.4 g) in dichloromethane (100 ml) at room temperature with triethylamine 4. 2 g was added. After the addition was completed, the reaction mixture was cooled to -20°C and 8.8 g of trimethylsilyl trifluoromethanesulfonate was added. After the addition was completed, the reaction mixture was stirred under ice cooling for 20 minutes. After completion of stirring, the reaction mixture was cooled to -20°C, and 14.1 g of trimethylphenylammonium tribromide was added. After the addition was completed, the reaction mixture was stirred under ice cooling for 30 minutes. After completion of the reaction, the reaction mixture was added dropwise to 100 ml of water under ice cooling and extracted with chloroform (100 ml×2). The obtained organic layer was dried over anhydrous sodium sulfate and dried, and then the solvent was distilled off under reduced pressure to obtain 13.4 g of the desired product as a reddish brown oily substance.

¹ H-NMR(CDCl ₃ ): δ8.90-8.80(m, 1H), 8.50-8.40(m, 1H), 7.14(s, 1H), 4.27(s, 3H), 3.05-2.80(m, 2H ), 1.39(t, J=7.6Hz, 3H).
Step 3: 2-[3-(ethylthio)-6-iodo-8-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl)- Synthesis of 3H-imidazo[4,5-b]pyridine (Compound of the present invention No. 1-1-066b) 300 mg of 5-iodo-3-(trifluoromethyl)pyridin-2-amine was dissolved in 8 ml of propionitrile. Then, at room temperature, 345 mg of 2-bromo-2-(ethylthio)-1-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl]ethanone was added. Was added. After completion of the addition, the reaction mixture was stirred under heating under reflux for 1.5 hours. After completion of the reaction, 20 ml of water was added to the reaction mixture, and the mixture was extracted with chloroform (20 ml×2). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. To the precipitated solid, 10 ml of diisopropyl ether was added and filtered to obtain 294 mg of the desired product as an orange solid.

Melting point: 222-225°C
¹ H-NMR(CDCl ₃ ): δ9.10-9.00(m, 1H), 8.75-8.70(m, 1H), 8.40-8.35(m, 1H), 7.90-7.85(m, 1H), 4.35(s , 3H), 3.18(q, J=7.4Hz, 2H), 1.24(t, J=7.4Hz, 3H).
Synthesis Example 28: 2-[3-(ethylthio)-7-(trifluoromethyl)imidazo[1,2-b]pyridazin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo [4,5-b]Pyridine (the present compound No. 1-1-057b), 2-[3-(ethylsulfonyl)-7-(trifluoromethyl)imidazo[1,2-b]pyridazine-2- Iyl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (inventive compound No. 1-1-057a) and 2-[3-(ethylsulfinyl)-7. -(Trifluoromethyl)imidazo[1,2-b]pyridazin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (Compound No. of the present invention. Synthesis of 1-1-057c) Step 1: 2-[3-(ethylthio)-7-(trifluoromethyl)imidazo[1,2-b]pyridazin-2-yl]-3-methyl-6-(tri Synthesis of Fluoromethyl)-3H-imidazo[4,5-b]pyridine (Compound No. 1-1-057b of the present invention) 42 mg of 5-(trifluoromethyl)pyridazin-3-amine was dissolved in 3 ml of acetonitrile, At room temperature, 100 mg of 2-bromo-2-(ethylthio)-1-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl]ethanone was added. .. After the addition was completed, the reaction mixture was stirred under heating to reflux for 2 hours. After completion of the reaction, 10 ml of water was added to the reaction mixture, and the mixture was extracted with chloroform (10 ml×2). The obtained organic layer was dried over anhydrous sodium sulfate and dried, and then the solvent was distilled off under reduced pressure to obtain 130 mg of a target product as a crude product. This product was used as it was in the next step without further purification.

Step 2: 2-[3-(ethylsulfonyl)-7-(trifluoromethyl)imidazo[1,2-b]pyridazin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo [4,5-b]Pyridine (the present compound No. 1-1-057a) and 2-[3-(ethylsulfinyl)-7-(trifluoromethyl)imidazo[1,2-b]pyridazine-2- Synthesis of [yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (inventive compound No. 1-1-057c) 2 of the crude product obtained in Step 1 -[3-(Ethylthio)-7-(trifluoromethyl)imidazo[1,2-b]pyridazin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5- b] 99 mg of 65 mass% metachloroperbenzoic acid (containing about 30 mass% water) was added to a solution of 120 mg of pyridine in 10 ml of chloroform under ice cooling. After the addition was complete, the reaction mixture was stirred at room temperature overnight. After completion of the reaction, saturated aqueous sodium thiosulfate solution was added to the reaction mixture, and the mixture was extracted with chloroform (10 ml×2). The obtained organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution, dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient of 100:0 to 50:50) to obtain the desired product, 2-[3-(. Ethylsulfonyl)-7-(trifluoromethyl)imidazo[1,2-b]pyridazin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine 70 mg And the target compound, 2-[3-(ethylsulfinyl)-7-(trifluoromethyl)imidazo[1,2-b]pyridazin-2-yl]-3-methyl-6-(trifluoromethyl)-3H. 41 mg of imidazo[4,5-b]pyridine were each obtained as a pale yellow oil.

2-[3-(ethylsulfonyl)-7-(trifluoromethyl)imidazo[1,2-b]pyridazin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4. ^1- H-NMR of 5-b]pyridine: δ8.90(d, J=1.8Hz, 1H), 8.79(d, J=1.5Hz, 1H), 8.55-8.50(m, 1H), 8.42(d, J=2.1Hz, 1H), 4.02(s, 3H), 3.75(q, J=7.5Hz, 2H), 1.46(t, J=7.5Hz, 3H).
2-[3-(ethylsulfinyl)-7-(trifluoromethyl)imidazo[1,2-b]pyridazin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4. ^1- H-NMR of 5-b]pyridine: δ8.82(d, J=2.1Hz, 1H), 8.78-8.74(m, 1H), 8.49-8.45(m, 1H), 8.42-8.38(m, 1H ), 4.36(s, 3H), 4.18-4.00(m, 1H), 3.85-3.70(m, 1H), 1.55(t, J=7.5Hz, 3H).
Synthesis Example 29: 5-(Ethylthio)-6-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl]-2-(trifluoromethyl)imidazo [2,1-b] [1,3,4]Thiadiazole (Compound No. 2-1-002b of the present invention) and 5-(ethylsulfonyl)-6-[3-methyl-6-(trifluoromethyl)- 3H-imidazo[4,5-b]pyridin-2-yl]-2-(trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazole (present compound No. 2-1 Synthesis of 002a) Step 1: 5-(Ethylthio)-6-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl]-2-(trifluoro) Synthesis of methyl)imidazo[2,1-b][1,3,4]thiadiazole (inventive compound No. 2-1-002b) 5-(trifluoromethyl)-1,3,4-thiadiazole-2- 195 mg of amine was dissolved in 5 ml of propionitrile, and 2-bromo-2-(ethylthio)-1-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b was dissolved at room temperature. ] Pyridin-2-yl]ethanone 400 mg was added. After the addition was completed, the reaction mixture was stirred under heating to reflux for 3 hours. After completion of the reaction, 10 ml of water was added to the reaction mixture, and the mixture was extracted with chloroform (10 ml×2). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient of 100:0 to 0:100) to obtain 130 mg of the desired product as a white solid.

¹ H-NMR(CDCl ₃ ): δ8.82(d, J=1.2Hz, 1H), 8.43(d, J=1.2Hz, 1H), 4.24(s, 3H), 2.66(q, J=7.5Hz , 2H), 1.31(t, J=7.5Hz, 3H).
Step 2: 5-(Ethylsulfonyl)-6-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl]-2-(trifluoromethyl)imidazo Synthesis of [2,1-b] [1,3,4]thiadiazole (Compound No. 2-1-002a of the Present Invention) 5-(Ethylthio)-6-[3-methyl-6-(trifluoromethyl)- 3H-imidazo[4,5-b]pyridin-2-yl]-2-(trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazole To a solution of 130 mg of chloroform in 10 ml of chloroform, ice-cooled. 191 mg of 65 wt% metachloroperbenzoic acid (containing about 30 wt% water) were added underneath. After the addition was complete, the reaction mixture was stirred at room temperature overnight. After completion of the reaction, saturated aqueous sodium thiosulfate solution was added to the reaction mixture, and the mixture was extracted with chloroform (10 ml×2). The obtained organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution, dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient of 100:0 to 50:50) to obtain 52 mg of the desired product as a white solid.

Melting point: 231-234°C
¹ H-NMR(CDCl ₃ ): δ8.76(s, 1H), 8.35(s, 1H), 4.11(s, 3H), 3.92(q, J=7.5Hz, 2H), 1.51(t, J= 7.5Hz, 3H).
Synthesis Example 30: 2-[3-(Ethylthio)-8-fluoro-6-iodoimidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo Synthesis of [4,5-c]pyridine (Compound No. 1-8-008b of the Present Invention) Step 1: 2-(Ethylthio)-1-[3-methyl-6-(trifluoromethyl)-3H-imidazo[ Synthesis of 4,5-c]pyridin-2-yl]ethanone 2-Bromo-1-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl] To a solution of 2.36 g of ethanone in 25 ml of N,N-dimethylformamide, 546 mg of ethanethiol and 1.21 g of potassium carbonate were sequentially added under ice cooling. After the addition was complete, the reaction mixture was stirred at room temperature for 1 hour. After completion of the reaction, 50 ml of water was added to the reaction mixture, and the mixture was extracted with ethyl acetate (50 ml×2). The obtained organic layer was dehydrated and dried over saturated saline and then anhydrous sodium sulfate in this order, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient of 100:0 to 80:20) to obtain 1.70 g of the desired product as a white solid. It was

Melting point: 90-93°C
¹ H-NMR(CDCl ₃ ): 9.03(s, 1H), 8.19(d, J=1.0Hz, 1H), 4.29(s, 3H), 4.08(s, 2H), 2.65(q, J=7.4Hz , 2H), 1.32(t, J=7.4Hz, 3H).
Step 2: Synthesis of 2-bromo-2-(ethylthio)-1-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl]ethanone 2-( To a solution of 1.63 g of ethylthio)-1-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl]ethanone in 15 ml of dichloromethane was added 600 mg of triethylamine at room temperature. Was added. After the addition was completed, 1.25 g of trimethylsilyl trifluoromethanesulfonate was added to the reaction mixture under ice cooling. After the addition was completed, the reaction mixture was stirred under ice cooling for 30 minutes. After completion of stirring, 2.02 g of trimethylphenylammonium tribromide was added to the reaction mixture under ice cooling. After the addition was completed, the reaction mixture was stirred under ice cooling for 1 hour. After completion of the reaction, the reaction mixture was added dropwise to 20 ml of water under ice cooling and extracted with chloroform (20 ml×2). The obtained organic layer was dried over anhydrous sodium sulfate and dried, and then the solvent was distilled off under reduced pressure to obtain 2.09 g of the desired product as a yellow oily substance.

¹ H-NMR(CDCl ₃ ): δ9.06(s, 1H), 8.19(s, 1H), 7.12(s, 1H), 4.31(s, 3H), 3.01-2.77(m, 2H), 1.39( t, J=7.5Hz, 3H).
Step 3: 2-[3-(ethylthio)-8-fluoro-6-iodoimidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[ Synthesis of 4,5-c]pyridine (invention compound No. 1-8-008b) 250 mg of 3-fluoro-5-iodopyridin-2-amine was dissolved in 5 ml of acetonitrile, and 2-bromo- 400 mg of 2-(ethylthio)-1-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl]ethanone was added. After the addition was completed, the reaction mixture was stirred with heating under reflux for 1 hour. After completion of the reaction, 10 ml of water was added to the reaction mixture, and the mixture was extracted with chloroform (10 ml×2). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The precipitated solid was filtered off by filtration to obtain 338 mg of the desired product as a brown solid.

¹ H-NMR(CDCl ₃ ): δ8.96(s, 1H), 8.73(d, J=1.5Hz, 1H), 8.19(d, J=0.9Hz, 1H), 7.33(dd, J=9.0, 1.5Hz, 1H), 4.36(s, 3H), 3.15(q, J=7.5Hz, 2H), 1.23(t, J=7.5Hz, 3H).
Reference Example 1: Synthesis of 2-bromo-1-[3-(ethylsulfonyl)-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]ethanone Step 1: Ethyl 7-(tri Synthesis of fluoromethyl)imidazo[1,2-a]pyridin-2-carboxylate 5.0 g of 4-(trifluoromethyl)pyridin-2-amine was dissolved in 50 ml of chlorobenzene, and ethyl 3-bromo-at room temperature. 6.67 g of 2-oxopropanoate was added. After the addition was complete, the reaction mixture was stirred with heating under reflux for 6.5 hours. After completion of the reaction, 20 ml of 1M aqueous sodium hydroxide solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate (20 ml×2). The obtained organic layer was dehydrated and dried over saturated saline and then anhydrous sodium sulfate in this order, and then the solvent was distilled off under reduced pressure. A 3M aqueous hydrochloric acid solution was added to the obtained residue, and the mixture was washed with 10 ml of ethyl acetate. Then, the aqueous layer was adjusted to pH 2 to 3 with 10 M aqueous sodium hydroxide solution, and then extracted with ethyl acetate (10 ml×2). The obtained organic layer was dehydrated and dried over saturated saline and then anhydrous sodium sulfate in this order, and then the solvent was distilled off under reduced pressure to obtain 3.94 g of the desired product as a yellow solid.

Melting point: 170-175°C
¹ H-NMR(CDCl ₃ ): δ8.29(s, 1H), 8.27(d, J=7.2Hz, 1H), 8.01(s, 1H), 7.07(dd, J=7.2, 1.7Hz, 1H) , 4.49(q, J=7.2Hz, 2H), 1.46(t, J=7.2Hz, 3H).
Step 2: Synthesis of ethyl 3-iodo-7-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylate Ethyl 7-(trifluoromethyl)imidazo[1,2-a]pyridine-2 -To a solution of 3.73 g of carboxylate in 20 ml of N,N-dimethylformamide was added 6.5 g of N-iodosuccinimide at room temperature. After the addition was complete, the reaction mixture was stirred at 80° C. for 5 hours. After the reaction was completed, water was added to the reaction mixture, and the precipitated solid was filtered off by filtration. The obtained solid was dissolved in 20 ml of chloroform, and washed with a saturated aqueous sodium thiosulfate solution and then saturated sodium hydrogencarbonate in this order. The organic layer obtained was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 5.08 g of the desired product as a flesh-colored solid.

Melting point: 183-185°C
¹ H-NMR(CDCl ₃ ): δ8.40(d, J=7.2Hz, 1H), 7.99(s, 1H), 7.17(dd, J=7.2, 1.7Hz, 1H), 4.53(q, J= 7.2Hz, 2H), 1.50(t, J=7.2Hz, 3H).
Step 3: Synthesis of ethyl 3-(ethylthio)-7-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylate Ethyl 3-iodo-7-(trifluoromethyl)imidazo[1,2 -A] Pyridine-2-carboxylate (5.73 g) in a solution of 1,4-dioxane (40 ml) at room temperature, diisopropylethylamine (5.79 g), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (862 mg) Then, 682 mg of tris(dibenzylideneacetone)dipalladium (zero valent) and 1.85 g of ethanethiol were sequentially added. After the addition was completed, the inside of the reaction vessel was replaced with nitrogen gas, and then the mixture was stirred under heating under reflux for 2 hours. After completion of the reaction, the reaction mixture was filtered through Celite, and Celite was washed with 30 ml of chloroform. The obtained filtrate and washing solution were combined, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient of 100:0 to 50:50) to obtain 5.58 g of the desired product as a brown solid. It was

Melting point: 50-52°C
¹ H-NMR(CDCl ₃ ): δ8.67(d, J=7.4Hz, 1H), 8.02-8.00(m, 1H), 7.15(dd, J=7.4, 1.8Hz, 1H), 4.52(q, J=7.0Hz, 2H), 2.98(q, J=7.5Hz, 2H), 1.48(t, J=7.0Hz, 3H), 1.20(t, J=7.5Hz, 3H).
Step 4: Synthesis of 3-(ethylthio)-7-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylic acid Ethyl 3-(ethylthio)-7-(trifluoromethyl)imidazo[1, To a solution of 5.58 g of 2-a]pyridine-2-carboxylate in 60 ml of ethanol and 30 ml of tetrahydrofuran was added 10 ml of a 3M aqueous sodium hydroxide solution at room temperature. After the addition was complete, the reaction 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. A 1 M aqueous hydrochloric acid solution was added to the obtained residue to adjust the pH of the aqueous layer to 2, and the mixture was extracted with ethyl acetate (20 ml×2). The obtained organic layer was dehydrated and dried over saturated saline and then anhydrous sodium sulfate in this order, and then the solvent was distilled off under reduced pressure to obtain 3.40 g of the desired product as a yellow solid.

Melting point: 163-171°C
¹ H-NMR(CDCl ₃ ): δ8.69(d, J=7.2Hz, 1H), 8.19(s, 1H), 7.22(dd, J=7.2, 1.4Hz, 1H), 3.06(q, J= 7.4Hz, 2H), 1.23(t, J=7.4Hz, 3H) (CO ₂ H proton peak could not be observed).
Step 5: Synthesis of 3-(ethylthio)-N-methoxy-N-methyl-7-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxamide 3-(ethylthio)-7-(tri To a solution of fluoromethyl)imidazo[1,2-a]pyridine-2-carboxylic acid (2.52 g) in dichloromethane (30 ml) was added oxalyl dichloride (3.31 g) and N,N-dimethylformamide (30 mg) under ice-cooling. After the addition was complete, the reaction mixture was stirred at room temperature for 3 hours. After completion of stirring, the solvent was distilled off from the reaction mixture under reduced pressure to obtain a crude product of 3-(ethylthio)-7-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylic acid. I got chloride. The crude 3-(ethylthio)-7-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylic acid chloride obtained was dissolved in 5 ml of dichloromethane and prepared in a separate container, N,O. A solution of 931 mg of dimethylhydroxylamine hydrochloride and 1.93 g of triethylamine in 15 ml of dichloromethane was added under ice cooling. After the addition was complete, the reaction mixture was stirred at room temperature for 1.5 hours. After completion of the reaction, 10 ml of water was added to the reaction mixture, and the mixture was extracted with chloroform (10 ml×2). The obtained organic layer was washed with dilute hydrochloric acid and a saturated aqueous solution of sodium hydrogencarbonate in this order, dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 2.50 g of the desired product as a flesh-colored solid. It was

Melting point: 82-84°C
¹ H-NMR(CDCl ₃ ): δ8.62(d, J=7.2Hz, 1H), 7.98-7.95(m, 1H), 7.14(dd, J=7.2, 1.7Hz, 1H), 3.80(s, 3H), 3.44(s, 3H), 2.91(q, J=7.4Hz, 2H), 1.22(t, J=7.4Hz, 3H).
Step 6: Synthesis of 1-[3-(ethylthio)-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]ethanone 3-(ethylthio)-N-methoxy under nitrogen atmosphere A solution of 2.45 g of -N-methyl-7-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxamide in 25 ml of tetrahydrofuran was added to a solution of about 3 M methylmagnesium bromide in diethyl ether under ice cooling. 0.7 ml was added. After the addition was completed, the reaction mixture was stirred under ice cooling for 1 hour. After completion of the reaction, the reaction mixture was added dropwise to 10 ml of 4M aqueous hydrochloric acid solution under ice cooling, and extracted with ethyl acetate (20 ml×2). The obtained organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate, dehydrated and dried in this order with saturated saline solution and anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 2.08 g of the desired product. Was obtained as a brown solid.

Melting point: 60-64°C
¹ H-NMR(CDCl ₃ ): δ8.67(d, J=7.2Hz, 1H), 8.03-7.99(m, 1H), 7.15(dd, J=7.2, 1.7Hz, 1H), 3.01(q, J=7.4Hz, 2H), 2.80(s, 3H), 1.18(t, J=7.4Hz, 3H).
Step 7: Synthesis of 1-[3-(ethylsulfonyl)-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]ethanone 1-[3-(ethylthio)-7-(tri To a solution of 2.08 g of fluoromethyl)imidazo[1,2-a]pyridin-2-yl]ethanone in 40 ml of methanol and 20 ml of water was added 13.3 g of Oxone (registered trademark of DuPont) under ice cooling. After the addition was complete, the reaction mixture was stirred at room temperature overnight. After completion of the reaction, a solution of 2.28 g of sodium thiosulfate in 25 ml of water was added to the reaction mixture, and then an aqueous solution of 10 M sodium hydroxide was added to make the aqueous layer alkaline, and then methanol was distilled off under reduced pressure. did. Ethyl acetate (40 ml×2) was added to the obtained residue for extraction. The obtained organic layer was dehydrated and dried over saturated saline and then with anhydrous sodium sulfate in this order, and then the solvent was distilled off under reduced pressure to obtain 2.11 g of the desired product as a yellow solid.

Melting point: 135-138°C
¹ H-NMR(CDCl ₃ ): δ9.44(d, J=7.5Hz, 1H), 8.12-8.09(m, 1H), 7.27-7.24(m, 1H), 3.80(q, J=7.5Hz, 2H), 2.80(s, 3H), 1.35(t, J=7.5Hz, 3H).
Step 8: Synthesis of 2-bromo-1-[3-(ethylsulfonyl)-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]ethanone 1-[3-(ethylsulfonyl) A solution of 2.05 g of -7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]ethanone in 15 ml of toluene was added with 10.2 g of acetic acid solution of about 5.1 M hydrogen bromide at 10°C. Bromine 1.13 g was added sequentially. After the addition was complete, the reaction mixture was stirred at room temperature for 2 hours. After completion of stirring, 205 mg of bromine was added to the reaction mixture, and the mixture was stirred at room temperature overnight. After completion of the reaction, 10 ml of water was added to the reaction mixture, and the mixture was extracted with ethyl acetate (20 ml×2). The obtained organic layer is washed with a 5% by mass aqueous solution of sodium hydrogen sulfite, dehydrated and dried over anhydrous sodium sulfate, and then the solvent is distilled off under reduced pressure to obtain 2.48 g of the desired product as a yellow solid. It was

Melting point: 122-123°C
¹ H-NMR(CDCl ₃ ): δ9.45(d, J=7.5Hz, 1H), 8.14-8.11(m, 1H), 7.33-7.27(m, 1H), 4.78(s, 2H), 3.78( q, J=7.4Hz, 2H), 1.37(t, J=7.4Hz, 3H).
Reference Example 2: Synthesis of 5-(ethylthio)-2-(trifluoromethyl)imidazo[2,1-b]thiazole-6-carboxylic acid Step 1: Ethyl 2-(trifluoromethyl)imidazo[2,1- b] Synthesis of thiazole-6-carboxylate 4.0 g of 5-(trifluoromethyl)thiazol-2-amine was dissolved in 80 ml of chlorobenzene, and 7.2 g of ethyl 3-bromo-2-oxopropanoate was added at room temperature. Was added. After the addition was completed, the reaction mixture was stirred under heating to reflux for 3 hours. After completion of stirring, 3.09 g of ethyl 3-bromo-2-oxopropanoate was added to the reaction mixture. After the addition was completed, the reaction mixture was stirred with heating under reflux for 1 hour. After completion of stirring, 2.4 g of ethyl 3-bromo-2-oxopropanoate was added to the reaction mixture. After the addition was completed, the reaction mixture was stirred under heating to reflux for 2 hours. After completion of the reaction, the solvent was distilled off from the reaction mixture under reduced pressure. A 1 M sodium hydroxide aqueous solution was added to the obtained residue to adjust the pH of the aqueous layer to 8, and the mixture was extracted with ethyl acetate (20 ml×3). The obtained organic layer was dehydrated and dried over saturated saline and then anhydrous sodium sulfate in this order, and then the solvent was distilled off under reduced pressure. The precipitated solid was filtered off by filtration. The obtained solid was washed with diisopropyl ether to give the desired product (2.12 g) as a white solid.

¹ H-NMR(CDCl ₃ ): δ8.14(s, 1H), 7.92(s, 1H), 4.42(q, J=7.5Hz, 2H), 1.43(t, J=7.5Hz, 3H).
Step 2: Synthesis of ethyl 5-iodo-2-(trifluoromethyl)imidazo[2,1-b]thiazole-6-carboxylate Ethyl 2-(trifluoromethyl)imidazo[2,1-b]thiazole-6 -To a solution of 7.97 g of carboxylate in 10 ml of N,N-dimethylformamide was added 3.58 g of N-iodosuccinimide at room temperature. After the addition was complete, the reaction mixture was stirred at 80° C. for 4 hours. After completion of the reaction, saturated sodium thiosulfate aqueous solution was added to the reaction mixture, and the precipitated solid was filtered off by filtration to obtain 3.09 g of the desired product as a white solid.

¹ H-NMR(CDCl ₃ ): δ7.90-7.86(m, 1H), 4.44(q, J=7.5Hz, 2H), 1.45(t, J=7.5Hz, 3H).
Step 3: Synthesis of ethyl 3-(ethylthio)-2-(trifluoromethyl)imidazo[2,1-b]thiazole-6-carboxylate Ethyl 5-iodo-2-(trifluoromethyl)imidazo[2,1 -B] thiazole-6-carboxylate 2.00 g, to a solution of 1,4-dioxane 20 ml, at room temperature diisopropylethylamine 1.98 g, 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene 296 mg , Tris(dibenzylideneacetone)dipalladium (zero valent) 234 mg and ethanethiol 636 mg were sequentially added. After the addition was completed, the inside of the reaction vessel was replaced with nitrogen gas, and then the mixture was stirred under heating under reflux for 4 hours. After completion of the reaction, the reaction mixture was filtered through Celite, and Celite was washed with 30 ml of chloroform. The obtained filtrate and washing solution were combined, and the solvent was distilled off under reduced pressure. The resulting residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient of 100:0 to 50:50) to obtain 1.11 g of the desired product as a yellow solid. It was

¹ H-NMR(CDCl ₃ ): δ8.04-7.98(m, 1H), 4.44(q, J=7.5Hz, 2H), 2.99(q, J=7.5Hz, 2H), 1.46(t, J= 7.5Hz, 3H), 1.23(t, J=7.5Hz, 3H).
Step 4: Synthesis of 5-(ethylthio)-2-(trifluoromethyl)imidazo[2,1-b]thiazole-6-carboxylic acid Ethyl 3-(ethylthio)-2-(trifluoromethyl)imidazo[2 To a solution of 1.09 g of 1-b]thiazole-6-carboxylate in 10 ml of ethanol and 10 ml of tetrahydrofuran was added 6.8 ml of a 1M aqueous sodium hydroxide solution at room temperature. After the addition was complete, the reaction mixture was stirred at room temperature overnight. After completion of the reaction, the solvent was distilled off from the reaction mixture under reduced pressure. A 1 M aqueous hydrochloric acid solution was added to the obtained residue to adjust the pH of the aqueous layer to 2-3, followed by extraction with chloroform (20 ml×2). The obtained organic layer was dried over anhydrous sodium sulfate and dried, and then the solvent was distilled off under reduced pressure to obtain 896 mg of the desired product as a yellow solid.

¹ H-NMR(CDCl ₃ ): 8.06-8.02(m, 1H), 3.04(q, J=7.5Hz, 2H), 1.25(t, J=7.5Hz, 3H) (CO ₂ H proton peak is I could not observe).
Reference Example 3: The following compounds were synthesized in the same manner as in Step 1 to Step 4 of Reference Example 1.

3-(Ethylthio)-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylic acid Melting point: 200-201°C
¹ H-NMR(CDCl ₃ ): δ8.93(s, 1H), 8.20(d, J=9.6Hz, 1H), 7.56(dd, J=9.6, 1.8Hz, 1H), 3.06(qJ=7.4Hz , 2H), 1.23(t, J=7.4Hz, 3H) (CO ₂ H proton peak could not be observed).
3-(Ethylthio)-6-(trifluoromethyl)imidazo[1,2-a]pyrazine-2-carboxylic acid Melting point: 175-178°C
¹ H-NMR(CDCl ₃ ): δ9.21(s, 1H), 8.84(s, 1H), 3.08(q, J=7.2Hz, 2H), 1.22(t, J=7.2Hz, 3H) (CO _{No 2} H proton peak could be observed).
Reference Example ^4: N 3, 2-dimethyl-6 synthesis steps (trifluoromethyl) pyridine-3,4-diamine 1: 4-Bromo-2-methyl-6- (trifluoromethyl) pyridin-3-amine Synthesis of 2-Methyl-6-(trifluoromethyl)pyridin-3-amine (3.0 g) was added to a solution of 3.0 g of acetonitrile in 30 ml of N-bromosuccinimide at room temperature. After the addition was complete, the reaction mixture was stirred at room temperature for 1.5 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient of 100:0 to 50:50) to obtain 4.0 g of the desired product as a brown solid. ..

Melting point: 40-41°C
¹ H-NMR(CDCl ₃ ): δ7.61(s, 1H), 4.40(brs, 2H), 2.52(s, 3H).
Step 2: Synthesis of 4-bromo-N,2-dimethyl-6-(trifluoromethyl)pyridin-3-amine 63 mass% sodium hydride (dispersed in mineral oil) 537 mg of N,N-dimethylformamide 5 ml solution. Then, under ice cooling, a solution of 4-bromo-2-methyl-6-(trifluoromethyl)pyridin-3-amine (3.0 g) in N,N-dimethylformamide (12 ml) was added. After the addition was complete, the reaction mixture was stirred at room temperature for 1 hour. After completion of stirring, 2.0 g of methyl iodide was added to the reaction mixture under ice cooling. 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 the mixture was extracted with ethyl acetate (10 ml×2). The obtained organic layer was dehydrated and dried over saturated saline and then anhydrous sodium sulfate in this order, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient 100:0 to 50:50) to give 2.82 g of the desired product as a yellow oil. Obtained.

¹ H-NMR(CDCl ₃ ): δ7.62(s, 1H), 3.01(s, 3H), 2.65(s, 3H) (NH proton peak could not be observed).
Step ^3: N 3, 2-dimethyl-6- Synthesis of 4-bromo -N (trifluoromethyl) pyridine-3,4-diamine, 2-dimethyl-6- (trifluoromethyl) pyridin-3-amine 1. A solution of 0 g, 186 mg of acetylacetone, 243 mg of acetylacetone copper (II) and 1.81 g of cesium carbonate in 30 ml of N-methylpyrrolidone was added to the autoclave reactor. After the addition was completed, 20 ml of 28 mass% aqueous ammonia was added to the reaction mixture at room temperature. After the addition was completed, the reaction vessel was sealed and the reaction mixture was heated to 140° C. and stirred for 1 hour. After completion of the reaction, 20 ml of water was added to the reaction mixture, and the mixture was extracted with ethyl acetate (20 ml×2). The obtained organic layer was dehydrated and dried over saturated saline and then anhydrous sodium sulfate in this order, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography eluting with n-hexane-ethyl acetate (gradient of 100:0 to 0:100) to obtain 189 mg of the desired product as a white solid.

¹ H-NMR(CDCl ₃ ): 6.84(s, 1H), 4.53(brs, 2H), 2.69(s, 3H), 2.50(s, 3H) (NH proton peak could not be observed).
Reference Example 5: Synthesis of 2-methyl-6-(perfluoroethyl)pyrimidin-4-amine Step 1: (Z)-Ethyl 3-ethoxy-4,4,5,5,5-pentafluoropent-2- Synthesis of Enoate A solution of 20.7 g of ethyl 4,4,5,5,5-pentafluoro-3-oxovalerate in 150 ml of acetone was added under ice-cooling 24.4 g of potassium carbonate and ethyl trifluoromethanesulfonate 15. 7 g were added sequentially. After the addition was complete, the reaction mixture was stirred at room temperature for 30 minutes. After completion of the reaction, the reaction mixture was filtered through Celite and the Celite was washed with 50 ml of acetone. The obtained filtrate and washing solution were combined, and the solvent was distilled off under reduced pressure. 30 ml of water was added to the obtained residue, and the mixture was extracted with hexane (30 ml×2). The obtained organic layer was dehydrated and dried over saturated saline and then anhydrous sodium sulfate in this order, and the solvent was distilled off under reduced pressure to obtain 20.53 g of the target product as a colorless transparent oily substance. It was

¹ H-NMR(CDCl ₃ ): δ5.80(s, 1H), 4.33(q, J=7.0Hz, 2H), 4.22(q, J=7.0Hz, 2H), 1.36(t, J=7.0Hz , 3H), 1.32(t, J=7.0Hz, 3H).
Step 2: Synthesis of 2-methyl-6-(perfluoroethyl)pyrimidin-4-ol Into a solution of 6.49 g of acetamidine hydrochloride in 75 ml of dimethyl sulfoxide, at 20° C., an ethanol solution of about 20% by mass sodium ethoxide was added. 23.3 g and (Z)-ethyl 3-ethoxy-4,4,5,5,5-pentafluoropent-2-enoate 15.0 g were added sequentially. After the addition was complete, the reaction mixture was stirred at 50° C. for 2 hours. After completion of stirring, 5.84 g of an ethanol solution of about 20 mass% sodium ethoxide was added to the reaction mixture at 50°C. After the addition was complete, the reaction mixture was stirred at 50° C. for 2.5 hours. After completion of stirring, the reaction mixture was stirred at room temperature overnight. After completion of the reaction, 50 ml of water was added to the reaction mixture, and the mixture was extracted with diethyl ether (50 ml×2). Concentrated hydrochloric acid was added to the obtained aqueous layer to adjust the pH of the aqueous layer to 1 to 2 and then extracted with chloroform (20 ml×2). The organic layer thus obtained was dried over anhydrous sodium sulfate and dried, and then the solvent was distilled off under reduced pressure to obtain 7.0 g of a target substance as a crude product as a white solid.

Melting point: 135-138°C
¹ H-NMR(CDCl ₃ ): δ6.77(s, 1H), 2.57(s, 3H) (OH proton peak could not be observed).
Step 3: Synthesis of 4-chloro-2-methyl-6-(perfluoroethyl)pyrimidine To a solution of 8.7 g of 2-methyl-6-(perfluoroethyl)pyrimidin-4-ol in 20 ml of thionyl chloride, at room temperature. Then, 30 mg of N,N-dimethylformamide was added. After the addition was completed, the reaction mixture was stirred with heating under reflux for 1 hour. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, added dropwise to ice water, and extracted with diethyl ether (20 ml×2). The obtained organic layer was dehydrated and dried over saturated saline and then with anhydrous sodium sulfate in this order, and the solvent was distilled off under reduced pressure to obtain 9.33 g of the target product as a reddish brown oily substance. ..

¹ H-NMR(CDCl ₃ ): δ7.54(s, 1H), 2.82(s, 3H).
Step 4: Synthesis of 2-methyl-6-(perfluoroethyl)pyrimidin-4-amine A solution of 9.33 g of crude 4-chloro-2-methyl-6-(perfluoroethyl)pyrimidine in 20 ml of acetonitrile was added, 20 ml of 28 mass% ammonia water was added at room temperature. After the addition was complete, the reaction mixture was stirred at room temperature for 3 days. After completion of the reaction, the solvent was distilled off from the reaction mixture under reduced pressure. 20 ml of water was added to the obtained residue, and the mixture was extracted with ethyl acetate (20 ml×2). The obtained organic layer was dehydrated and dried over saturated saline and then anhydrous sodium sulfate in this order, and then the solvent was distilled off under reduced pressure to obtain 6.75 g of the desired product as a reddish brown solid.

Melting point: 95-105°C
¹ H-NMR(CDCl ₃ ): δ6.61(s, 1H), 5.12(brs, 2H), 2.59(s, 3H).
Reference Example 6: The following compounds were synthesized in the same manner as in Steps 1 to 4 of Reference Example 5.

6-(perfluoroethyl)pyrimidin-4-amine
¹ H-NMR(CDCl ₃ ): δ8.70(s, 1H), 6.79(s, 1H), 5.22(brs, 2H).
Reference Example 7: Synthesis of 4-chloro-6-(perfluoroethyl)nicotinaldehyde Step 1: Synthesis of 4-chloro-6-(perfluoroethyl)nicotinic acid 2,2,6,6-tetra under nitrogen atmosphere To a solution of 4.04 g of methylpiperidine in 20 ml of tetrahydrofuran was added 17.9 ml of an n-hexane solution of about 1.6 M n-butyllithium at -78°C. After the addition was complete, the reaction mixture was warmed to 0° C. and stirred for 10 minutes. After completion of stirring, the reaction mixture was cooled to −78° C., and a solution of 6-(perfluoroethyl)nicotinic acid (2.3 g) in tetrahydrofuran (20 ml) was added. After the addition was completed, the reaction mixture was heated to -40°C and stirred for 1.5 hours. After completion of stirring, the reaction mixture was cooled to −78° C. and 4.5 g of hexachloroethane was added. After the addition was complete, the reaction mixture was stirred at -78°C for 1.5 hours. After completion of the reaction, 25 ml of a saturated aqueous solution of ammonium chloride was added to the reaction mixture at -78°C. After the addition was completed, the reaction mixture was warmed to room temperature, adjusted to pH 9 with a 1.0 M aqueous sodium hydroxide solution, and washed with diethyl ether (20 ml). Concentrated hydrochloric acid was added to the obtained aqueous layer to adjust the pH of the aqueous solution to 2, and the mixture was extracted with ethyl acetate (20 ml×2). The obtained organic layer was dehydrated and dried over saturated saline and then anhydrous sodium sulfate in this order, and the solvent was distilled off under reduced pressure to give the desired product, 4-chloro-6-(perfluoroethyl)nicotine. 1.08 g of acid was obtained as a brown oil.

¹ H-NMR(CDCl ₃ ): δ9.25(s, 1H), 7.84(s, 1H) (CO ₂ H proton peak could not be observed).
Step 2: Synthesis of [4-chloro-6-(perfluoroethyl)pyridin-3-yl]methanol To a solution of 1.0 g of 4-chloro-6-(perfluoroethyl)nicotinic acid in 10 ml of tetrahydrofuran was added -50°C. Then, 8.5 ml of a tetrahydrofuran solution of 0.85 M borane-tetrahydrofuran complex was added. After the addition was complete, the reaction mixture was warmed to room temperature and stirred overnight. After completion of the reaction, the reaction mixture was added dropwise to a 1M aqueous hydrochloric acid solution under ice cooling and extracted with ethyl acetate (20 ml×2). The obtained organic layer was dehydrated and dried over saturated saline and then with anhydrous sodium sulfate in this order, and the solvent was distilled off under reduced pressure to obtain the desired product, [4-chloro-6-(perfluoroethyl)]. Pyridin-3-yl]methanol (950 mg) was obtained as an orange oil.

¹ H-NMR (CDCl ₃ ): δ 8.87 (s, 1H), 7.71 (s, 1H), 4.92 (s, 2H) (OH proton peak could not be observed).
Step 3: Synthesis of 4-chloro-6-(perfluoroethyl)nicotinaldehyde [4-chloro-6-(perfluoroethyl)pyridin-3-yl]methanol in a solution of 930 mg of dichloromethane in 10 ml of dichloromethane at room temperature, 3 g of silicon dioxide. And 1.53 g of pyridinium chlorochromate were sequentially added. After the addition was complete, the reaction mixture was stirred at room temperature for 1 hour. After completion of stirring, 500 mg of pyridinium chlorochromate was added to the reaction mixture. After the addition was complete, the reaction mixture was stirred at room temperature for 30 minutes. After completion of the reaction, the reaction mixture was filtered through Celite, and the Celite was washed with 100 ml of n-hexane-ethyl acetate [2:1 (volume ratio)]. The obtained filtrate and washing solution were combined, and the solvent was distilled off under reduced pressure. The obtained residue was purified by preparative medium pressure liquid chromatography under elution with n-hexane-ethyl acetate (gradient 100:0 to 30:70) to obtain 154 mg of the desired product as a yellow oil.

¹ H-NMR(CDCl ₃ ): δ 10.54(s, 1H), 9.14(s, 1H), 7.84(s, 1H).
Reference Example 8: The following compounds were synthesized in the same manner as in Steps 1 to 3 of Reference Example 7.

4-chloro-6-(trifluoromethyl)nicotinaldehyde
¹ H-NMR(CDCl ₃ ): δ 10.54(s, 1H), 9.12(s, 1H), 7.81(s, 1H).
Reference Example 9: Synthesis of 3-nitro-5-(trifluoromethyl)picolinaldehyde 930 mg of selenium dioxide and 1.46 g of 2-methyl-3-nitro-5-(trifluoromethyl)pyridine of 10 ml of 1,4-dioxane. The solution was stirred with heating under reflux for 8 hours. After completion of stirring, the reaction mixture was filtered through Celite, and Celite was washed with 10 ml of 1,4-dioxane. The obtained filtrate and washing solution were combined, the solvent was evaporated under reduced pressure, saturated aqueous sodium hydrogen carbonate solution (5 ml) was added, and the mixture was extracted with ethyl acetate (10 ml×2). The obtained organic layer was dehydrated and dried over saturated saline and then anhydrous sodium sulfate in this order, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient 100:0 to 50:50). 10 ml of toluene was added to the residue obtained by concentration, and the solvent was distilled off under reduced pressure. Next, 10 ml of toluene was added, and the solvent was distilled off under reduced pressure to obtain 1.07 g of the desired product as a brown liquid.

¹ H-NMR(CDCl ₃ ): δ 10.32(s, 1H), 9.25-9.20(m, 1H), 8.53-8.49(m, 1H).
Reference Example 10: Synthesis of 3-(ethylthio)-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-amine Step 1: tert-butyl [3-(ethylthio)-7-(trifluoro Synthesis of methyl)imidazo[1,2-a]pyridin-2-yl]carbamate 3-(ethylthio)-7-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylic acid 3.0 g To a 30 ml solution of 2-methyl-2-propanol, 3.14 g of triethylamine and 3.40 g of diphenylphosphoryl azide were added at room temperature. After the addition was complete, the reaction mixture was stirred with heating under reflux for 2 hours. After completion of the reaction, the solvent was distilled off from the reaction mixture. 20 ml of water was added to the obtained residue, and the mixture was extracted with ethyl acetate (20 ml×2). The obtained organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution, dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (50:50) to obtain 2.12 g of the desired product as a pale yellow solid.

¹ H-NMR(CDCl ₃ ): δ8.42(d, J=7.0Hz, 1H), 7.93-7.88(m, 1H), 7.13-7.01(m, 2H), 2.68(q, J=7.4Hz, 2H), 1.56(s, 9H), 1.21(t, J=7.4Hz, 3H).
Step 2: Synthesis of 3-(ethylthio)-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-amine tert-butyl [3-(ethylthio)-7-(trifluoromethyl)imidazo[ 2.1 ml of trifluoroacetic acid was added to a solution of 2.0 g of 1,2-a]pyridin-2-yl]carbamate in 10 ml of dichloromethane under ice cooling. After the addition was complete, the reaction mixture was stirred at room temperature for 30 minutes. After completion of stirring, 10 ml of trifluoroacetic acid was added to the reaction mixture. After the addition was complete, the reaction mixture was stirred at room temperature for 30 minutes. After completion of the reaction, the solvent was distilled off from the reaction mixture. 20 ml of water was added to the obtained residue, and the mixture was extracted with chloroform (20 ml×2). The obtained organic layer was washed with 1M aqueous sodium hydroxide solution, dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 1.69 g of the desired product as a yellow oily substance. ..

¹ H-NMR(CDCl ₃ ): δ8.31(d, J=7.0Hz, 1H), 7.63-7.58(m, 1H), 6.98(dd, J=7.0, 1.6Hz, 1H), 4.41(brs, 2H), 2.63(q, J=7.4Hz, 2H), 1.21(t, J=7.4Hz, 3H).
Reference Example 11: Synthesis of 3-(ethylthio)-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxamide 3-(ethylthio)-6-(trifluoromethyl)imidazo[1, To a solution of 1.34 g of 2-a]pyridine-2-carboxylic acid in 20 ml of dichloromethane, 882 mg of oxalyl dichloride and 10 mg of N,N-dimethylformamide were added under ice cooling. After the addition was complete, the reaction mixture was stirred at room temperature for 2.5 hours. After completion of stirring, the solvent was distilled off from the reaction mixture under reduced pressure to obtain a crude product of 3-(ethylthio)-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylic acid. I got chloride. 28% by mass of the obtained crude 3-(ethylthio)-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylic acid chloride was dissolved in 2 ml of tetrahydrofuran and prepared in another container. It was added to 20 ml of ammonia water under ice cooling. After the addition was completed, the reaction mixture was stirred under ice cooling for 30 minutes. After completion of the reaction, 10 ml of water was added to the reaction mixture, and the mixture was extracted with chloroform (10 ml×2). The obtained organic layer was dried over anhydrous sodium sulfate and dried, and then the solvent was distilled off under reduced pressure to obtain 1.8 g of the target product as a pale yellow solid.

¹ H-NMR(CDCl ₃ ): δ8.90(s, 1H), 7.71(d, J=9.4Hz1H), 7.47(dd, J=9.4, 2.0Hz, 1H), 7.38(brs, 1H), 5.66 (brs, 1H), 3.03(q, J=7.4Hz, 2H), 1.21(t, J=7.4Hz, 3H).
Reference Example 12: Synthesis of 2-bromo-1-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl]ethanone Step 1: (S)-1 - [3-methyl-6- (trifluoromethyl) -3H- imidazo [4,5-b] pyridin-2-yl] synthesis of ethanol N ² - methyl-5- (trifluoromethyl) pyridine-2,3 -37.7 g of diamine was dissolved in 150 ml of pyridine, and 32.8 g of (S)-(-)-2-acetoxypropionyl chloride was added at -20°C. After the addition was complete, the reaction mixture was stirred at room temperature for 30 minutes. After completion of stirring, the solvent was distilled off from the reaction mixture under reduced pressure. The obtained residue was dissolved in 150 ml of ethanol, and 39.4 ml of 10M sodium hydroxide aqueous solution was added at room temperature. After the addition was completed, the reaction mixture was stirred under heating to reflux for 2 hours. After completion of stirring, 20 ml of 10M aqueous sodium hydroxide solution was added to the reaction mixture at room temperature. After the addition was completed, the reaction mixture was stirred with heating under reflux for 4.5 hours. After completion of the reaction, the solvent was distilled off from the reaction mixture under reduced pressure. Concentrated hydrochloric acid was added to the obtained residue to adjust the pH of the aqueous solution to 4, and then the mixture was extracted with ethyl acetate (100 ml×2). The obtained organic layer was dehydrated and dried over saturated saline and then anhydrous sodium sulfate in this order, and then the solvent was distilled off under reduced pressure to obtain the desired product (S)-1-[3-methyl-6]. 59.8 g of -(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl]ethanol was obtained as a black solid.

¹ H-NMR(CDCl ₃ ): δ8.65(s, 1H), 8.23(s, 1H), 5.20(brs, 1H), 3.97(s, 3H), 2.99(brs, 1H), 1.75(d, J=6.3Hz, 3H).
Step 2: Synthesis of 1-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl]ethanone (S)-1-[3-Methyl-6- A solution of 48.3 g of (trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl]ethanol in 200 ml of acetic acid is heated to 90° C., and 14.8 g of chromium (VI) oxide in water is added. A 50 ml solution was added. After completion of the addition, the reaction mixture was stirred under heating under reflux for 1.5 hours. After completion of stirring, a solution of 5 g of chromium(VI) oxide in 10 ml of water was added to the reaction mixture at 90°C. After completion of the addition, the reaction mixture was stirred under heating under reflux for 1.5 hours. After completion of the reaction, the reaction mixture was added dropwise to 800 ml of water at room temperature. The precipitated solid was filtered off by filtration. The obtained solid was washed with water to give the desired product, 1-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl]ethanone 35. 0.6 g was obtained as a brown solid.

Melting point: 106-108°C
¹ H-NMR(CDCl ₃ ): δ8.82(d, J=1.5Hz, 1H), 8.43(d, J=1.5Hz, 1H), 4.23(s, 3H), 2.86(s, 3H).
Step 3: Synthesis of 2-bromo-1-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl]ethanone 1-[3-methyl-6- (Trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl]ethanone (35.6 g) was dissolved in 300 ml of toluene and 150 ml of an acetic acid solution of about 5.1 M hydrogen bromide, and the mixture was cooled with ice. 25.8 g of bromine was added. After the addition was complete, the reaction mixture was stirred at room temperature for 2 hours. After completion of stirring, 3.12 g of bromine was added to the reaction mixture at room temperature. After the addition was complete, the reaction mixture was stirred at room temperature for 1 hour. After completion of stirring, 2.58 g of bromine was added to the reaction mixture at room temperature. After the addition was complete, the reaction mixture was stirred at room temperature for 30 minutes. After completion of the reaction, the reaction mixture was adjusted to pH 3 by adding a 10 M aqueous sodium hydroxide solution under ice cooling, and then extracted with toluene (200 ml×2). The obtained organic layer was washed with a saturated aqueous solution of sodium hydrogen sulfite, dehydrated and dried with saturated saline and then with anhydrous sodium sulfate in this order, and then the solvent was distilled off under reduced pressure. The precipitated solid was filtered off by filtration. The obtained solid was washed with diisopropyl ether to give the desired product, 2-bromo-1-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl. ] 36.6 g of ethanone was obtained as a white solid.

Melting point: 90-91°C
¹ H-NMR(CDCl ₃ ): δ8.86(d, J=1.8Hz, 1H), 8.47(d, J=1.8Hz, 1H), 4.85(s, 2H), 4.26(s, 3H).
Reference Example 13: Synthesis of 2-bromo-1-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl]ethanone Step 1: (S)-1 - [3-methyl-6- (trifluoromethyl) -3H- imidazo [4,5-c] pyridin-2-yl] synthesis of ethanol N ³ - methyl-6- (trifluoromethyl) pyridine-3,4 3.34 g of diamine was dissolved in 20 ml of pyridine, and 2.89 g of (S)-(−)-2-acetoxypropionyl chloride was added at −20° C. After the addition was complete, the reaction mixture was stirred at room temperature for 20 minutes. After completion of stirring, the solvent was distilled off from the reaction mixture under reduced pressure. The obtained residue was dissolved in 20 ml of ethanol, and 3.5 ml of 10M aqueous sodium hydroxide solution was added at room temperature. After the addition was completed, the reaction mixture was stirred with heating under reflux for 1 hour. After completion of stirring, 1.8 ml of 10M aqueous sodium hydroxide solution was added to the reaction mixture at room temperature. After the addition was completed, the reaction mixture was stirred under heating to reflux for 2 hours. After completion of the reaction, 50 ml of water was added to the reaction mixture, and the mixture was extracted with ethyl acetate (50 ml×2). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient of 100:0 to 50:50) to obtain 3.0 g of the desired product as a light pink solid. Got as.

Melting point: 97-100°C
¹ H-NMR(CDCl ₃ ): δ8.84(s, 1H), 8.04(d, J=0.7Hz, 1H), 5.31-5.14(m, 1H), 4.02(s, 3H), 3.03(d, J=7.2Hz, 1H), 1.78(d, J=6.5Hz, 3H).
Step 2: Synthesis of 1-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl]ethanone (S)-1-[3-Methyl-6- A solution of (trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl]ethanol (3.0 g) in acetic acid (30 ml) was heated to 90° C., and chromium (VI) oxide (1.22 g) in water was added. 10 ml solution was added. After the addition was completed, the reaction mixture was stirred with heating under reflux for 1 hour. After completion of the reaction, 50 ml of water was added to the reaction mixture, and the mixture was extracted with ethyl acetate (50 ml×2). After dehydrating and drying the obtained organic layer with anhydrous sodium sulfate, the solvent was distilled off under reduced pressure to obtain 1-[3-methyl-6-(trifluoromethyl)-3H-imidazo which is the target product. 2.59 g of [4,5-c]pyridin-2-yl]ethanone was obtained as a pale yellow solid.

Melting point: 136-140°C
¹ H-NMR(CDCl ₃ ): δ9.03(s, 1H), 8.19(d, J=0.9Hz, 1H), 4.28(s, 3H), 2.89(s, 3H).
Step 3: Synthesis of 2-bromo-1-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl]ethanone 1-[3-methyl-6- To a solution of 2.55 g of (trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl]ethanone in 30 ml of dichloromethane was added 1.16 g of triethylamine at room temperature. After the addition was completed, 2.44 g of trimethylsilyl trifluoromethanesulfonate was added to the reaction mixture under ice cooling. After the addition was completed, the reaction mixture was stirred under ice cooling for 30 minutes. After completion of stirring, 3.95 g of trimethylphenylammonium tribromide was added to the reaction mixture under ice cooling. After the addition was completed, the reaction mixture was stirred under ice cooling for 30 minutes. After completion of the reaction, 50 ml of water was added to the reaction mixture and extracted with chloroform (30 ml×2). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The precipitated solid was filtered off by filtration. The obtained solid was washed with n-hexane to give the desired product, 2-bromo-1-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine-2-. 2.66 g of [yl]ethanone was obtained as a white solid.

Melting point: 127-131°C
¹ H-NMR(CDCl ₃ ): δ9.07(s, 1H), 8.21(d, J=1.0Hz, 1H), 4.87(s, 2H), 4.31(s, 3H).
Reference Example 14: Synthesis of 1-[3-(ethylsulfonyl)-6-iodoimidazo[1,2-a]pyridin-2-yl]ethan-1-one Step 1: 3-(Ethylthio)-6-iodo Synthesis of ethyl imidazo[1,2-a]pyridine-2-carboxylate To a mixed solution of 785 mg of ethanethiol and 20 ml of 1,2-dichloroethane, 1.27 g of N-chlorosuccinimide was added under ice cooling. After the addition was complete, the reaction mixture was stirred at room temperature for 30 minutes. After completion of stirring, 2.0 g of ethyl 6-iodoimidazo[1,2-a]pyridine-2-carboxylate was added to the reaction mixture at room temperature. After the addition was completed, the reaction mixture was stirred with heating under reflux for 5 hours. After the completion of stirring, a solution of 3.80 g of N-chlorosuccinimide and 2.35 g of ethanethiol prepared in another container in 60 ml of 1,2-dichloroethane was added to the reaction mixture at room temperature. After the addition was completed, the reaction mixture was stirred with heating under reflux for 5 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. 20 ml of water was added to the obtained residue, and the mixture was extracted with ethyl acetate (20 ml×2). The obtained organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate, dried over saturated brine and then dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography (n-hexane:ethyl acetate = 100:0 to 0:100 gradient) to obtain 1.5 g of the desired product as a white solid.
Melting point: 110-112°C
Step 2: Synthesis of 3-(ethylthio)-6-iodoimidazo[1,2-a]pyridine-2-carboxylic acid 3-(Ethylthio)-6-iodoimidazo[1,2-a]pyridine-2-carboxylic acid To a mixed solution of 16.5 g of ethyl acidate and 45 ml of ethanol, 90 ml of a 1 mol/L sodium hydroxide aqueous solution was added under ice cooling. After the addition was complete, the reaction mixture was stirred at room temperature for 17 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. 12 mol/L hydrochloric acid was added to the obtained residue to adjust the pH to 2, and the precipitated solid was filtered to obtain 13.68 g of the desired product as an orange solid.
Melting point: 214-215°C
Step 3: Synthesis of dimethyl 2-[3-(ethylthio)-6-iodoimidazo[1,2-a]pyridine-2-carbonyl]malonate 3-(ethylthio)-6-iodoimidazo[1,2-a ] To a mixed solution of 4.0 g of pyridine-2-carboxylic acid and 50 ml of dichloromethane, 2.92 g of oxalyl dichloride and 30 mg of N,N-dimethylformamide were sequentially added under ice cooling. After the addition was complete, the reaction mixture was stirred at room temperature for 3 hours. After completion of stirring, the solvent was distilled off from the reaction mixture under reduced pressure to obtain crude 3-(ethylthio)-6-iodoimidazo[1,2-a]pyridine-2-carboxylic acid chloride. .. The obtained crude 3-(ethylthio)-6-iodoimidazo[1,2-a]pyridine-2-carboxylic acid chloride was dissolved in 10 ml of dichloromethane, and 2.29 g of dimethyl malonate prepared in another container, It was added to a mixed solution of 1.65 g of magnesium chloride, 3.49 g of triethylamine and 20 ml of acetonitrile under ice cooling. After the addition was complete, the reaction mixture was stirred at room temperature for 2 hours. After the reaction was completed, 1 mol/L hydrochloric acid was added to the reaction mixture to adjust the pH to 4, and the mixture was extracted with chloroform (30 ml×2). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography (n-hexane:ethyl acetate=100:0 to 0:100 gradient) to obtain 3.95 g of the desired product as a brown oil.
¹ H-NMR (CDCl ₃ ): δ8.76 (dd, J=1.5, 0.9Hz, 1H), 7.50 (dd, J=9.3, 1.5Hz, 1H), 7.41 (dd, J=9.3, 0.9Hz, 1H), 5.78 (s, 1H), 3.80 (s, 6H), 2.99 (q, J=7.5Hz, 2H), 1.20 (t, J=7.5Hz, 3H).
Step 4: Synthesis of 1-[3-(ethylthio)-6-iodoimidazo[1,2-a]pyridin-2-yl]ethan-1-one 2-[3-(ethylthio)-6-iodoimidazo[ To a mixed solution of 3.95 g of dimethyl 1,2-a]pyridine-2-carbonyl]malonate, 2 ml of water and 20 ml of dimethyl sulfoxide, 362 mg of lithium chloride was added at room temperature. After the addition was complete, the reaction mixture was stirred at 150° C. for 3 hours. After the reaction was completed, 40 ml of water was added to the reaction mixture at room temperature. The precipitated solid was filtered to obtain 2.42 g of the desired product as a light brown solid.
Melting point: 147-149°C
Step 5: Synthesis of 1-[3-(ethylsulfonyl)-6-iodoimidazo[1,2-a]pyridin-2-yl]ethan-1-one 1-[3-(ethylthio)-6-iodoimidazo In a mixed solution of 2.11 g of [1,2-a]pyridin-2-yl]ethan-1-one and 20 ml of chloroform, 65% by mass of metachloroperbenzoic acid (about 30% by mass of water was added under ice cooling). 3.60 g (including) was added. After the addition was complete, the reaction mixture was stirred at room temperature for 3 hours. After completion of the reaction, 10 ml of saturated aqueous sodium thiosulfate solution was added to the reaction mixture, and the mixture was extracted with chloroform (20 ml×2). The obtained organic layer was washed with 30 ml of a 1 mol/L sodium hydroxide aqueous solution, dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 2.19 g of the desired product as a brown solid. Obtained.
Melting point: 110-133°C
The compound of the present invention can be synthesized according to the above-mentioned production methods and synthetic examples. Examples of the fused heterocyclic compounds produced in the same manner as in Synthesis Examples 1 to 30 are shown in Tables 14 to 32, and examples of their intermediates are shown in Tables 33 to 40. The fused heterocyclic compounds included in the present invention and intermediates for producing them are not limited thereto.

In the table, “Me” represents a methyl group, and similarly, “Et” represents an ethyl group, “Pr-c” represents a cyclopropyl group, “Bu-n” represents a normal butyl group, and “Bu-t” represents a tertiary butyl group, “Ph” represents a phenyl group, “Ac” represents an acetyl group, and “TMS” represents a trimethylsilyl group. The substituents represented by Z1 to Z21 in the table represent the following structures. Further, in the table, "*1" indicates that the compound is a solid, "*2" indicates that the compound is an oil or resin, and "*5" indicates when the melting point of the compound is measured. "M.p." represents the melting point (unit: °C). Further, in the description of melting points in the table, “>” indicates that the melting point of the compound is higher than the indicated temperature. For example, the expression “>250” means that the compound did not melt at 250° C.

[Table 14]

―――――――――――――――――――――――――――――――――――――――
No. R ³ R ⁴ A ^1a G ₁ G ₂ G ₃ G ₄ n mp
―――――――――――――――――――――――――――――――――――――――
1-1-001a CF ₃ H Me CH C-CF ₃ CH CH 2 212-213
1-1-001b CF ₃ H Me CH C-CF ₃ CH CH 0 208-209
1-1-001c CF ₃ H Me CH C-CF ₃ CH CH 1 202-203
1-1-002a CF ₃ H Me CH CH C-CF ₃ CH 2 203-205
1-1-002b CF ₃ H Me CH CH C-CF ₃ CH 0 199-202
1-1-003a CF ₃ H Me CH C-Cl CH CH 2 217-218
1-1-003b CF ₃ H Me CH C-Cl CH CH 0 228-230
1-1-003c CF ₃ H Me CH C-Cl CH CH 1 217-219
1-1-004a CF ₃ H Me CH CF CH CH 2 187-189
1-1-004b CF ₃ H Me CH CF CH CH 0 190-195
1-1-004c CF ₃ H Me CH CF CH CH 1 195-200
1-1-005a CF ₃ H Me CH CI CH CH 2 215-218
1-1-005b CF ₃ H Me CH CI CH CH 0 260-263
1-1-005c CF ₃ H Me CH CI CH CH 1 239-241
1-1-006a CF ₃ H Me CH C-Br CH CH 2 205-207
1-1-006b CF ₃ H Me CH C-Br CH CH 0 233-236
1-1-007a CF ₃ H Me CH C-OMe CH CH 2 186-188
1-1-007b CF ₃ H Me CH C-OMe CH CH 0 209-211
1-1-008a CF ₃ H Me CH C-NO ₂ CH CH 2 258-262
1-1-008b CF ₃ H Me CH C-NO ₂ CH CH 0 218-221
1-1-009a CF ₃ H Me CH C-Me CH CH 2 162-165
1-1-010a CF ₃ H Me CH C-Z1 CH CH 2 *2
1-1-011a CF ₃ H Me CH C-SCF ₃ CH CH 2 208-210
1-1-012a CF ₃ H Me CH CH CH CH 2 122-125
1-1-012b CF ₃ H Me CH CH CH CH 0 183-184
1-1-013a CF ₃ H Me CH CH C-Cl CH 2 214-215
1-1-013b CF ₃ H Me CH CH C-Cl CH 0 198-203
1-1-013c CF ₃ H Me CH CH C-Cl CH 1 *1
1-1-014a CF ₃ H Me CH CH CF CH 2 170-171
1-1-014b CF ₃ H Me CH CH CF CH 0 210-212
1-1-014c CF ₃ H Me CH CH CF CH 1 *5
1-1-015a CF ₃ H Me CH CH CI CH 2 208-211
1-1-015b CF ₃ H Me CH CH CI CH 0 202-205
1-1-016a CF ₃ H Me CH CH C-Br CH 2 205-206
1-1-016b CF ₃ H Me CH CH C-Br CH 0 204-206
1-1-016c CF ₃ H Me CH CH C-Br CH 1 *5
1-1-017a CF ₃ H Me CH CH C-Me CH 2 136-138
1-1-018a CF ₃ H Me CH CH C-CN CH 2 253-255
1-1-019a CF ₃ H Me CH CH C-CO ₂ H CH 2 210-214
1-1-020a CF ₃ H Me CH C-CF ₃ CH C-Cl 2 192-195
1-1-020b CF ₃ H Me CH C-CF ₃ CH C-Cl 0 138-144
1-1-021b CF ₃ H Me CH C-CF ₃ CH C-SEt 0 190-192
1-1-022a CF ₃ H Me CH C-CF ₃ CH C-SO ₂ Et 2 *1
1-1-023a CF ₃ H Me CH C-Br C-CF ₃ CH 2 226-228
1-1-023b CF ₃ H Me CH C-Br C-CF ₃ CH 0 214-215
1-1-023c CF ₃ H Me CH C-Br C-CF ₃ CH 1 198-200
1-1-024a CF ₃ H Me CH C-Me C-CF ₃ CH 2 247-250
1-1-025b CF ₃ H Me C-Me CH C-Me CH 0 156-158
1-1-025c CF ₃ H Me C-Me CH C-Me CH 1 *2
1-1-026a IH Me CH CH C-CF ₃ CH 2 202-205
1-1-026b IH Me CH CH C-CF ₃ CH 0 230-233
1-1-027a SCF ₃ H Me CH CH C-CF ₃ CH 2 220-223
1-1-027b SCF ₃ H Me CH CH C-CF ₃ CH 0 209-210
1-1-028b Z1 H Me CH CH C-CF ₃ CH 0 94-96
1-1-029a CF ₃ H Me CH C-CF ₃ N CH 2 234-236
1-1-029b CF ₃ H Me CH C-CF ₃ N CH 0 220-222
1-1-030a H CF ₃ Me CH CH C-CF ₃ CH 2 217-219
1-1-030b H CF ₃ Me CH CH C-CF ₃ CH 0 163-165
1-1-030c H CF ₃ Me CH CH C-CF ₃ CH 1 190-200
1-1-031b H CF ₃ H CH CH C-CF ₃ CH 0 *5
1-1-032a CF ₃ H Et CH CH C-CF ₃ CH 2 215-217
1-1-032b CF ₃ H Et CH CH C-CF ₃ CH 0 199-202
1-1-033a CF ₃ H Me CH CH C-CO ₂ Me CH 2 199-202
1-1-034a CF ₃ H Me CH CH C-CO ₂ Et CH 2 192-194
1-1-035a CF ₃ H Me CH CH C-CONMe ₂ CH 2 155-157
1-1-036a CF ₃ H Me CH C-SMe C-CF ₃ CH 2 192-202
1-1-037a CF ₃ H Me CH C-Z1 C-CF ₃ CH 2 77-79
1-1-038a CF ₃ H Me CH C-SO ₂ Me C-CF ₃ CH 2 *1
1-1-039a CF ₃ H Me CH C-SOMe C-CF ₃ CH 2 220-223
1-1-040a CF ₃ H Me C-CF ₃ CH CH CH 2 196-200
1-1-040b CF ₃ H Me C-CF ₃ CH CH CH 0 131-133
1-1-040c CF ₃ H Me C-CF ₃ CH CH CH 1 175-178
1-1-041a CF ₃ H Me CH CH C-Z1 CH 2 75-77
1-1-042a CF ₃ H Me CH CH C-SMe CH 2 194-196
1-1-043a CF ₃ H Me CH CH C-SOMe CH 2 226-228
1-1-044a CF ₃ H Me CH CH C-SO ₂ Me CH 2 290-292
1-1-045a CF ₃ H Me CH C-CF ₂ CF ₃ CH CH 2 208-210
1-1-045b CF ₃ H Me CH C-CF ₂ CF ₃ CH CH 0 165-167
1-1-046a CF ₃ H Me CH C-Cl C-Cl CH 2 224-225
1-1-047a CF ₃ H Me CH CI C-Cl CH 2 268-270
1-1-047b CF ₃ H Me CH CI C-Cl CH 0 239-243
1-1-048a CF ₃ H Me CH CI C-Me CH 2 231-234
1-1-048b CF ₃ H Me CH CI C-Me CH 0 *1
1-1-049a CF ₃ H Me CH CI C-CF ₃ CH 2 240-243
1-1-049b CF ₃ H Me CH CI C-CF ₃ CH 0 222-225
1-1-050a CF ₃ H Me CH CI C-CN CH 2 290-297
1-1-050b CF ₃ H Me CH CI C-CN CH 0 284-290
1-1-051a CF ₃ H Me CH CI CF CH 2 *1
1-1-051b CF ₃ H Me CH CI CF CH 0 *1
1-1-052a CF ₃ H Me CH CI C-OMe CH 2 251-253
1-1-052b CF ₃ H Me CH CI C-OMe CH 0 240-244
1-1-053a CF ₃ H Me CH CI CH N 2 292-295
1-1-053b CF ₃ H Me CH CI CH N 0 275-278
1-1-054a CF ₃ H Me CH C-CF ₃ CH N 2 244-248
1-1-054b CF ₃ H Me CH C-CF ₃ CH N 0 220-222
1-1-055a CF ₃ H Me CH N C-CF ₃ CH 2 238-240
1-1-055b CF ₃ H Me CH N C-CF ₃ CH 0 198-200
1-1-056a CF ₃ H Me CH CI N CH 2 205-210
1-1-057a CF ₃ H Me N CH C-CF ₃ CH 2 *2
1-1-057b CF ₃ H Me N CH C-CF ₃ CH 0 *2
1-1-057c CF ₃ H Me N CH C-CF ₃ CH 1 *2
1-1-058a CF ₃ H Me CH C-Cl CH C-Me 2 198-200
1-1-058b CF ₃ H Me CH C-Cl CH C-Me 0 199-202
1-1-059a CF ₃ H Me CH C-Cl CH C-Cl 2 220-224
1-1-059b CF ₃ H Me CH C-Cl CH C-Cl 0 222-225
1-1-060a CF ₃ H Me CH CF CH CF 2 190-192
1-1-060b CF ₃ H Me CH CF CH CF 0 181-185
1-1-061a CF ₃ H Me CH CI CH CI 2 277-279
1-1-061b CF ₃ H Me CH CI CH CI 0 267-270
1-1-062a CF ₃ H Me CH CI CH C-Cl 2 240-243
1-1-062b CF ₃ H Me CH CI CH C-Cl 0 248-251
1-1-063a CF ₃ H Me CH C-Br CH CF 2 229-231
1-1-063b CF ₃ H Me CH C-Br CH CF 0 202-205
1-1-064a CF ₃ H Me CH CI CH C-OMe 2 239-241
1-1-065a CF ₃ H Me CH CI CH C-OEt 2 220-221
1-1-066a CF ₃ H Me CH CI CH C-CF ₃ 2 271-273
1-1-066b CF ₃ H Me CH CI CH C-CF ₃ 0 222-225
1-1-067a CF ₃ H Me CH CI CH C-CN 2 253-256
1-1-067b CF ₃ H Me CH CI CH C-CN 0 298-300
1-1-068a CF ₃ H Me CH CI CH C-NMe ₂ 2 202-203
1-1-069a CF ₃ H Me CH C-Cl CH C-CF ₃ 2 218-220
1-1-069b CF ₃ H Me CH C-Cl CH C-CF ₃ 0 201-203
1-1-070a CF ₃ H Me CH C-CF ₃ CH CF 2 195-196
1-1-070b CF ₃ H Me CH C-CF ₃ CH CF 0 169-171
1-1-071a CF ₃ H Me CH C-CF ₃ CH CI 2 240-243
1-1-071b CF ₃ H Me CH C-CF ₃ CH CI 0 227-229
1-1-072a CF ₃ H Me CH CI CH C-Me 2 204-206
1-1-072b CF ₃ H Me CH CI CH C-Me 0 214-216
1-1-072c CF ₃ H Me CH CI CH C-Me 1 *5
1-1-073a CF ₃ H Me CH C-Me CH C-Cl 2 233-236
1-1-073b CF ₃ H Me CH C-Me CH C-Cl 0 213-218
1-1-074a CF ₃ H Me CH CI CH CF 2 222-226
1-1-074b CF ₃ H Me CH CI CH CF 0 232-236
1-1-075a CF ₃ H Me CH C-SMe CH C-SMe 2 205-214
1-1-076a CF ₃ H Me CH C-CF ₃ CH C-Br 2 219-220
1-1-077a CF ₃ H Me CH CH CH C-CF ₃ 2 199-202
1-1-077b CF ₃ H Me CH CH CH C-CF ₃ 0 195-197
1-1-078a CF ₃ H Me CH C-Cl C-Cl C-Cl 2 *1
1-1-078b CF ₃ H Me CH C-Cl C-Cl C-Cl 0 *1
1-1-079a CF ₃ H Me CH C-Ph CH CH 2 220-221
1-1-080a CF ₃ H Me CH C-Z2 CH CH 2 235-238
1-1-081a CF ₃ H Me CH C-Z3 CH CH 2 204-207
1-1-082a CF ₃ H Me CH C-Z4 CH CH 2 227-229
1-1-083a CF ₃ H Me CH C-Z5 CH CH 2 187-189
1-1-084a CF ₃ H Me CH C-Z6 CH CH 2 217-220
1-1-085a CF ₃ H Me CH C-Z7 CH CH 2 213-215
1-1-086a CF ₃ H Me CH C-Z8 CH CH 2 224-228
1-1-087a CF ₃ H Me CH C-Z9 CH CH 2 231-233
1-1-088a CF ₃ H Me CH C-Z10 CH CH 2 213-214
1-1-089a CF ₃ H Me CH C-Z11 CH CH 2 175-178
1-1-090a CF ₃ H Me CH C-Z12 CH CH 2 201-204
1-1-091a CF ₃ H Me CH C-Z13 CH CH 2 197-200
1-1-092a Cl H Me CH C-CF ₃ CH CH 2 181-183
1-1-092b Cl H Me CH C-CF ₃ CH CH 0 224-228
1-1-093a CF ₂ CF ₃ H Me CH C-Cl CH CH 2 185-187
1-1-093b CF ₂ CF ₃ H Me CH C-Cl CH CH 0 169-171
1-1-094a CF ₂ CF ₃ H Me CH CI CH CH 2 207-208
1-1-094b CF ₂ CF ₃ H Me CH CI CH CH 0 225-230
1-1-094c CF ₂ CF ₃ H Me CH CI CH CH 1 220-223
1-1-095a CF ₃ H Me CH C-SMe CH CH 2 198-200
1-1-096a CF ₃ H Me CH C-SOMe CH CH 2 230-232
1-1-097a CF ₃ H Me CH C-SO ₂ Me CH CH 2 225-230
1-1-098a CF ₃ H Me CH C-SCH ₂ CF ₃ CH CH 2 229-233
1-1-099a CF ₂ CF ₃ H Me CH C-SMe CH CH 2 175-181
1-1-100a CF ₃ H Me CH C-Z14 CH CH 2 215-216
1-1-101a CF ₃ H Me CH CH C-NO ₂ CH 2 230-232
1-1-101b CF ₃ H Me CH CH C-NO ₂ CH 0 231-233
1-1-102a HH Me CH CH C-CF ₃ CH 2 180-183
1-1-102b HH Me CH CH C-CF ₃ CH 0 182-184
1-1-103a CF ₂ CF ₃ H Me CH CH C-CF ₃ CH 2 229-232
1-1-103b CF ₂ CF ₃ H Me CH CH C-CF ₃ CH 0 186-188
1-1-104a CF ₃ H Me CH C-Z15 C-CF ₃ CH 2 *5
1-1-105a CF ₃ H Me CH C-CF ₃ CH C-CN 2 238-241
1-1-105a CF ₃ H Me CH C-CF ₃ CH C-CN 0 187-190
1-1-105a CF ₃ H Me CH C-CF ₃ CH C-CN 1 152-155
1-1-106a CF ₃ H Me CH CH C-CHF ₂ CH 2 164-165
1-1-106b CF ₃ H Me CH CH C-CHF ₂ CH 0 191-193
1-1-106c CF ₃ H Me CH CH C-CHF ₂ CH 1 191-194
1-1-107a CF ₃ H Me CH C-NH ₂ CH CH 2 *2
1-1-108a CF ₃ H Me CH C-Z16 CH CH 2 *2
1-1-109a CF ₃ H Me CH C-Br CF CH 2 240-242
1-1-109b CF ₃ H Me CH C-Br CF CH 0 250-253
1-1-110a CF ₃ H Me CH C-Br C-Cl CH 2 238-242
1-1-110c CF ₃ H Me CH C-Br C-Cl CH 1 298-300
1-1-111a CF ₃ H Me CH C-Br C-CN CH 2 255-268
1-1-111b CF ₃ H Me CH C-Br C-CN CH 0 246-248
1-1-112a CF ₃ H Me CH C-Br CH C-Cl 2 220-221
1-1-112b CF ₃ H Me CH C-Br CH C-Cl 0 223-226
1-1-113a CF ₃ H Me CH CF CH C-Cl 2 171-175
1-1-113b CF ₃ H Me CH CF CH C-Cl 0 204-208
1-1-114a CF ₃ H Me CH C-Cl CI CH 2 238-241
1-1-114b CF ₃ H Me CH C-Cl CI CH 0 *1
1-1-115a CF ₃ H Me CH C-Cl C-Br CH 2 220-224
1-1-115b CF ₃ H Me CH C-Cl C-Br CH 0 *1
1-1-116a CF ₃ H Me CH C-Cl C-SMe CH 2 248-251
1-1-117a CF ₃ H Me CH C-Cl C-SOMe CH 2 254-256
1-1-118a CF ₃ H Me CH C-Cl CH C-Br 2 219-223
1-1-118b CF ₃ H Me CH C-Cl CH C-Br 0 233-235
1-1-118c CF ₃ H Me CH C-Cl CH C-Br 1 *5
1-1-119b CF ₃ H Me CH C-Cl C-Me C-Cl 0 230-232
1-1-119c CF ₃ H Me CH C-Cl C-Me C-Cl 1 *5
1-1-120c CF ₃ H Me CH CH N CH 1 *5
1-1-121a CF ₃ H Me CH CF CI CH 2 243-245
1-1-122a SOCF ₃ H Me CH CH C-CF ₃ CH 2 218-219
1-1-123a SO ₂ CF ₃ H Me CH CH C-CF ₃ CH 2 241-243
1-1-124a SCF ₃ H Me CH C-CF ₃ CH CH 2 205-208
1-1-124b SCF ₃ H Me CH C-CF ₃ CH CH 0 202-204
1-1-125a SOCF ₃ H Me CH C-CF ₃ CH CH 2 195-196
1-1-126a SO ₂ CF ₃ H Me CH C-CF ₃ CH CH 2 222-224
1-1-127a SCF ₃ H Me CH C-Cl CH CH 2 173-174
1-1-127b SCF ₃ H Me CH C-Cl CH CH 0 219-220
1-1-128a SOCF ₃ H Me CH C-Cl CH CH 2 221-223
1-1-129a SO ₂ CF ₃ H Me CH C-Cl CH CH 2 199-201
1-1-130a SCF ₃ H Me CH CF CH CH 2 155-156
1-1-130b SCF ₃ H Me CH CF CH CH 0 196-198
1-1-131a SOCF ₃ H Me CH CF CH CH 2 *1
1-1-132a SCF ₃ H Me CH CI CH CH 2 206-208
1-1-133a SOCF ₃ H Me CH CI CH CH 2 220-223
1-1-134a SO ₂ CF ₃ H Me CH CI CH CH 2 234-235
1-1-135a SCF ₃ H Me CH C-Br CH CH 2 186-187
1-1-135b SCF ₃ H Me CH C-Br CH CH 0 216-217
1-1-136a SOCF ₃ H Me CH C-Br CH CH 2 234-236
1-1-137a SO ₂ CF ₃ H Me CH C-Br CH CH 2 238-241
1-1-138a SOCF ₃ H Me CH C-CN CH CH 2 204-206
1-1-139a SCF ₃ H Me CH CH C-Cl CH 2 220-221
1-1-139b SCF ₃ H Me CH CH C-Cl CH 0 205-207
1-1-140a SOCF ₃ H Me CH CH C-Cl CH 2 230-232
1-1-141a SO ₂ CF ₃ H Me CH CH C-Cl CH 2 248-249
1-1-142a SCF ₃ H Me CH CH CI CH 2 217-219
1-1-142b SCF ₃ H Me CH CH CI CH 0 190-192
1-1-143a SOCF ₃ H Me CH CH CI CH 2 237-240
1-1-144a SO ₂ CF ₃ H Me CH CH CI CH 2 268-269
1-1-145a SCF ₃ H Me CH CH C-Br CH 2 221-223
1-1-145b SCF ₃ H Me CH CH C-Br CH 0 219-221
1-1-146a SOCF ₃ H Me CH CH C-Br CH 2 240-241
1-1-147a SO ₂ CF ₃ H Me CH CH C-Br CH 2 248-250
1-1-148a SCF ₃ H Me CH CH C-CN CH 2 288-290
1-1-148b SCF ₃ H Me CH CH C-CN CH 0 238-239
1-1-149a SOCF ₃ H Me CH CH C-CN CH 2 283-284
1-1-150a SCF ₃ H Me CH CI CF CH 2 259-260
1-1-151a SOCF ₃ H Me CH CI CF CH 2 259-260
1-1-152a SO ₂ CF ₃ H Me CH CI CF CH 2 284-285
1-1-153a SCF ₃ H Me CH C-Cl CH C-Cl 2 214-215
1-1-153b SCF ₃ H Me CH C-Cl CH C-Cl 0 195-196
1-1-154a SOCF ₃ H Me CH C-Cl CH C-Cl 2 205-206
1-1-155a SO ₂ CF ₃ H Me CH C-Cl CH C-Cl 2 197-198
1-1-156a SCF ₃ H Me CH C-Cl CH CF 2 196-198
1-1-157a SOCF ₃ H Me CH C-Cl CH CF 2 233-235
1-1-158a SO ₂ CF ₃ H Me CH C-Cl CH CF 2 206-208
1-1-159a SCF ₃ H Me CH CI CH CF 2 191-194
1-1-159b SCF ₃ H Me CH CI CH CF 0 280-285
1-1-160a SOCF ₃ H Me CH CI CH CF 2 201-204
1-1-161a SO ₂ CF ₃ H Me CH CI CH CF 2 235-237
1-1-162a SCF ₃ H Me CH CI CH C-CN 2 262-263
1-1-163a SOCF ₃ H Me CH CI CH C-CN 2 265-266
1-1-164a SO ₂ CF ₃ H Me CH CI CH C-CN 2 282-283
1-1-165a SOCF ₃ H Me CH C-CF ₃ CH C-Cl 2 *2
1-1-166a SOCF ₃ H Me CH C-CF ₃ CH CF 2 202-203
1-1-167a SCF ₃ H Me CH C-CN CH C-Cl 2 213-215
1-1-168a SOCF ₃ H Me CH C-CN CH C-Cl 2 *2
1-1-169a SCF ₃ H Me CH C-Br CH C-Cl 2 190-192
1-1-169b SCF ₃ H Me CH C-Br CH C-Cl 2 227-229
1-1-170a SOCF ₃ H Me CH C-Br CH C-Cl 2 206-208
1-1-171a CF ₂ CF ₃ H Me CH C-CF ₃ CH CH 2 184-185
1-1-171b CF ₂ CF ₃ H Me CH C-CF ₃ CH CH 0 176-178
1-1-172a CF ₃ H Me CH C-Br N CH 2 258-259
1-1-172b CF ₃ H Me CH C-Br N CH 0 70-74
1-1-173a CF ₃ H Me CH CH N CH 2 *1
1-1-173b CF ₃ H Me CH CH N CH 0 228-230
1-1-174a CF ₃ H Me CH C-Z6 N CH 2 261-262
1-1-175a SOCF ₃ H Me CH CI N CH 2 260-265
1-1-176a CF ₃ H Me CH CH C-Z17 CH 2 204-205
1-1-177a CF ₃ H Me CH CH C-Z18 CH 2 214-215
1-1-178a CF ₃ H Me CH CH C-Z19 CH 2 247-248
1-1-179a CF ₃ H Me CH CH C-Z20 CH 2 198-201
1-1-180a CF ₃ H Me CH CH C-Z21 CH 2 189-192
1-1-181a CF ₃ H Me CH CH C-Ac CH 2 168-172
1-1-182a CF ₃ H Me CH C-CN CH CH 2 250-252
1-1-182b CF ₃ H Me CH C-CN CH CH 0 220-222
1-1-183a CF ₃ H Me CH C-Br CH C-Br 2 250-252
1-1-183b CF ₃ H Me CH C-Br CH C-Br 0 220-222
1-1-184a CF ₃ H Me CH CH CH C-Z14 2 215-217
1-1-185a CF ₃ H Me CH CH CH C-Z22 2 *2
1-1-186a CF ₃ H Me CH CH CI C-NH ₂ 2 172-174
1-1-187a CF ₃ H Me CH CH C-Br C-NH ₂ 2 201-202
1-1-188a CF ₃ H Me C-Cl CH C-Cl C-NH ₂ 2 212-213
1-1-189a CF ₃ H Me CH CH C-NH ₂ C-Br 2 *2
1-1-190a CF ₃ H Me CH CH C-NHMe CH 2 152-154
1-1-191a CF ₃ H Me CH CH C-Z26 CH 2 185-189
1-1-192a CF ₃ H Me CH CH C-Z23 CH 2 148-151
1-1-193a CF ₃ H Me CH CH C-Z24 CH 2 146-149
1-1-194a CF ₃ H Me CH CH C-Z14 CH 2 206-209
1-1-195a CF ₃ H Me CH CH C-Z16 CH 2 *2
1-1-196a CF ₃ H Me CH CH C-Z25 CH 2 138-140
1-1-197a CF ₃ H Me CH CH C-NHAc CH 2 267-269
1-1-198a CF ₃ H Me CH CH C-NH ₂ CH 2 *1
1-1-199a CF ₃ H Me CH CH CH C-NH ₂ 2 212-213
―――――――――――――――――――――――――――――――――――――――
[Table 15]

――――――――――――――――――――――――――――――――――――――
No. R ³ A ⁵ G ₁ G ₂ G ₃ G ₄ n mp
――――――――――――――――――――――――――――――――――――――
1-2-001a SO ₂ CF ₃ CH CH C-CF ₃ CH CH 2 *1
1-2-002a SOCF ₃ CH CH C-CF ₃ CH CH 2 *1
1-2-003b SCF ₃ CH CH C-CF ₃ CH CH 0 *1
1-2-004a CF ₃ N CH CH C-CF ₃ CH 2 244-246
1-2-004b CF ₃ N CH CH C-CF ₃ CH 0 159-161
1-2-004c CF ₃ N CH CH C-CF ₃ CH 1 175-177
1-2-005a SCF ₃ CH CH CH C-CF ₃ CH 2 217-219
1-2-006a SO ₂ CF ₃ CH CH CH C-CF ₃ CH 2 198-199
――――――――――――――――――――――――――――――――――――――
[Table 16]

―――――――――――――――――――――――――――――――――――――
No. R ³ R ⁵ R ⁶ G ₁ G ₂ G ₃ G ₄ n mp
―――――――――――――――――――――――――――――――――――――
1-3-001a CF ₃ HH CH CH C-CF ₃ CH 2 235-237
1-3-002a CF ₃ Me H CH CH C-CF ₃ CH 2 218-223
1-3-003a CF ₂ CF ₃ Me H CH CH C-CF ₃ CH 2 218-222
1-3-004a CF ₂ CF ₃ HH CH CH C-CF ₃ CH 2 228-232
1-3-005a CF ₃ HH CH C-CF ₃ CH CH 2 165-168
1-3-006a CF ₃ Me H CH C-CF ₃ CH CH 2 207-213
1-3-007a CF ₂ CF ₃ Me H CH C-CF ₃ CH CH 2 224-226
1-3-008a CF ₂ CF ₃ HH CH C-CF ₃ CH CH 2 233-239
1-3-009a CF ₂ CF ₃ HI CH C-CF ₃ CH CH 2 196-198
1-3-010a CF ₂ CF ₃ H Br CH C-CF ₃ CH CH 2 200-205
1-3-011a CF ₂ CF ₃ H Me CH C-CF ₃ CH CH 2 223-225
1-3-012a CF ₃ HH CH CI CH CH 2 *1
1-3-013a CF ₂ CF ₃ HI CH CH C-CF ₃ CH 2 254-258
1-3-014a CF ₂ CF ₃ H Me CH CH C-CF ₃ CH 2 277-279
1-3-015a CF ₃ H Me CH C-CF ₃ CH CH 2 294-296
―――――――――――――――――――――――――――――――――――――
[Table 17]

―――――――――――――――――――――――――――――――――――
No. R ³ G ₁ G ₂ G ₃ G ₄ n mp
―――――――――――――――――――――――――――――――――――
1-4-001a CF ₃ CH CH C-CF ₃ CH 2 214-218
1-4-002a CF ₃ CH C-CF ₃ CH CH 2 235-238
1-4-003a CF ₃ CH CI CH CH 2 253-258
1-4-003b CF ₃ CH CI CH CH 0 220-225
1-4-004a CF ₃ CH C-Br CH CH 0 241-243
―――――――――――――――――――――――――――――――――――
[Table 18]

―――――――――――――――――――――――――――――――――――――
No. R ³ R ⁴ G ₁ G ₂ G ₃ G ₄ n mp
―――――――――――――――――――――――――――――――――――――
1-5-001a CF ₃ H CH CH C-CF ₃ CH 2 142-144
1-5-002a CF ₃ H CH C-CF ₃ CH CH 2 245-248
1-5-003a H CF ₃ CH CH C-CF ₃ CH 2 175-177
1-5-004a H CF ₃ CH C-CF ₃ CH CH 2 138-143
―――――――――――――――――――――――――――――――――――――
[Table 19]

―――――――――――――――――――――――――――――――――――
No. R ⁴ G ₁ G ₂ G ₃ G ₄ n mp
―――――――――――――――――――――――――――――――――――
1-6-001a CF ₃ CH CH C-CF ₃ CH 2 200-202
1-6-002a CF ₃ CH C-CF ₃ CH CH 2 266-270
―――――――――――――――――――――――――――――――――――
[Table 20]

――――――――――――――――――――――――――――――――――――――
No. R ³ R ⁴ A ^1a G ₁ G ₂ G ₃ G ₄ n mp
――――――――――――――――――――――――――――――――――――――
1-7-001a CF ₃ H Me CH CH C-CF ₃ CH 2 190-200
1-7-001b CF ₃ H Me CH CH C-CF ₃ CH 0 164-166
――――――――――――――――――――――――――――――――――――――
[Table 21]

――――――――――――――――――――――――――――――――――――――
No. R ³ R ⁵ A ^1a G ₁ G ₂ G ₃ G ₄ n mp
――――――――――――――――――――――――――――――――――――――
1-8-001b CF ₃ HH CH C-CF ₃ CH CH 0 233-235
1-8-002a CF ₃ H Me CH C-CF ₃ CH CH 2 253-256
1-8-002b CF ₃ H Me CH C-CF ₃ CH CH 0 226-228
1-8-003a CF ₃ Me Me CH C-CF ₃ CH CH 2 200-205
1-8-003b CF ₃ Me Me CH C-CF ₃ CH CH 0 169-171
1-8-004b CF ₃ HH CH CH C-CF ₃ CH 0 96-98
1-8-005a CF ₃ H Me CH CH C-CF ₃ CH 2 245-247
1-8-005b CF ₃ H Me CH CH C-CF ₃ CH 0 217-219
1-8-006a CF ₃ H Me CH CH C-Cl CH 2 217-219
1-8-006b CF ₃ H Me CH CH C-Cl CH 0 215-217
1-8-007a CF ₃ H Me CH CI CH CH 2 *1
1-8-007b CF ₃ H Me CH CI CH CH 0 280-282
1-8-008a CF ₃ H Me CH CI CH CF 2 294-298
1-8-008b CF ₃ H Me CH CI CH CF 0 *1
1-8-009a CF ₃ H Me CH CI CH C-OEt 2 257-259
1-8-010a CF ₃ H Me CH CH CI CH 2 235-237
1-8-011a CF ₃ H Me CH C-Br CH CF 2 266-268
1-8-012b CF ₃ HH CH CH C-Cl CH 0 *1
1-8-013a CF ₃ H Me CH C-Br CH CH 2 270-272
1-8-013b CF ₃ H Me CH C-Br CH CH 0 240-242
1-8-013c CF ₃ H Me CH C-Br CH CH 1 238-240
1-8-014a CF ₃ H Me CH CI C-CN CH 2 280-284
1-8-014b CF ₃ H Me CH CI C-CN CH 0 248-253
1-8-015a CF ₃ H Me CH CI CF CH 2 294-297
1-8-015b CF ₃ H Me CH CI CF CH 0 259-263
1-8-016a CF ₃ H Me CH C-Cl CH CH 2 239-241
1-8-016b CF ₃ H Me CH C-Cl CH CH 0 238-242
――――――――――――――――――――――――――――――――――――――
[Table 22]

――――――――――――――――――――――――――――――――――――――
No. R ² R ⁴ A ^1a G ₁ G ₂ G ₃ G ₄ n mp
――――――――――――――――――――――――――――――――――――――
1-9-001a H CF ₃ Me CH C-CF ₃ CH CH 2 269-271
1-9-001b H CF ₃ Me CH C-CF ₃ CH CH 0 230-232
1-9-002a H CF ₃ Me CH CH C-CF ₃ CH 2 185-187
1-9-002b H CF ₃ Me CH CH C-CF ₃ CH 0 175-177
1-9-003a H CF ₃ Me CH CH C-Cl CH 2 200-202
1-9-003b H CF ₃ Me CH CH C-Cl CH 0 187-188
――――――――――――――――――――――――――――――――――――――
[Table 23]

――――――――――――――――――――――――――――――――――――――
No. R ³ A ⁵ G ₁ G ₂ G ₃ G ₄ n mp
――――――――――――――――――――――――――――――――――――――
1-10-001a CF ₃ CH CH CH C-CF ₃ CH 2 206-209
1-10-001b CF ₃ CH CH CH C-CF ₃ CH 0 126-130
1-10-001c CF ₃ CH CH CH C-CF ₃ CH 1 184-188
1-10-002a CF ₃ N CH CH C-CF ₃ CH 2 245-247
1-10-002b CF ₃ N CH CH C-CF ₃ CH 0 161-163
1-10-002c CF ₃ N CH CH C-CF ₃ CH 1 *1
1-10-003a CF ₃ N CH CI CH CH 2 260-265
1-10-003b CF ₃ N CH CI CH CH 0 249-251
1-10-004a SCF ₃ CH CH CH C-CF ₃ CH 2 188-190
1-10-005a CF ₃ N CH CH CI CH 2 253-255
1-10-006a CF ₃ CH CH CH CI CH 2 224-226
――――――――――――――――――――――――――――――――――――――
[Table 24]

――――――――――――――――――――――――――――――――――――
No. R ³ G ₁ G ₂ G ₃ G ₄ n mp
――――――――――――――――――――――――――――――――――――
1-11-001a CF ₃ CH CH C-CF ₃ CH 2 230-233
1-11-001b CF ₃ CH CH C-CF ₃ CH 0 183-185
1-11-001c CF ₃ CH CH C-CF ₃ CH 1 189-192
1-11-002a CF ₃ CH CH CI CH 2 231-233
1-11-003a CF ₃ CH CI CH CH 2 276-283
1-11-003b CF ₃ CH CI CH CH 0 *5
1-11-004a CF ₃ CH C-CF ₃ CH CH 2 225-227
1-11-004b CF ₃ CH C-CF ₃ CH CH 0 185-187
1-11-004c CF ₃ CH C-CF ₃ CH CH 1 195-198
1-11-005a CF ₃ CH C-Br CH CF 2 254-256
1-11-005b CF ₃ CH C-Br CH CF 0 199-201
1-11-006a CF ₃ CH CI CH CF 2 283-286
1-11-006b CF ₃ CH CI CH CF 0 258-260
1-11-007a CF ₃ CH C-Br CH CH 2 250-255
1-11-007b CF ₃ CH C-Br CH CH 0 249-251
1-11-007c CF ₃ CH C-Br CH CH 1 198-202
1-11-008a CF ₂ CF ₃ CH C-CF ₃ CH CH 2 207-209
1-11-008b CF ₂ CF ₃ CH C-CF ₃ CH CH 0 182-184
1-11-009a CF ₃ CH CH C-CF ₃ CH 2 210-220
1-11-009b CF ₃ CH CH C-CF ₃ CH 0 192-194
――――――――――――――――――――――――――――――――――――
[Table 25]

――――――――――――――――――――――――――――――――――――――
No. R ⁷ R ⁶ A ⁸ G ₁ G ₂ G ₃ G ₄ n mp
――――――――――――――――――――――――――――――――――――――
1-12-001a CF ₃ H CH CH C-CF ₃ CH CH 2 219-220
1-12-002a CF ₂ CF ₃ H CH CH C-CF ₃ CH CH 2 188-194
1-12-003a CF ₂ CF ₃ H C-Me CH C-CF ₃ CH CH 2 182-186
1-12-004a CF ₃ H CH CH CH C-CF ₃ CH 2 198-200
1-12-005a CF ₂ CF ₃ H C-Me CH CH C-CF ₃ CH 2 233-236
1-12-006a CF ₃ HN CH C-CF ₃ CH CH 2 204-207
1-12-007a CF ₂ CF ₃ HN CH C-CF ₃ CH CH 2 194-196
1-12-008a CF ₃ HN CH CH C-CF ₃ CH 2 153-155
1-12-009a CF ₃ HN CH CI CH CH 2 *1
1-12-010a CF ₂ CF ₃ Me N CH C-CF ₃ CH CH 2 *1
1-12-011a CF ₂ CF ₃ Me CH CH C-CF ₃ CH CH 2 268-271
1-12-011a CF ₃ HN CH C-Br CH CH 2 228-229
――――――――――――――――――――――――――――――――――――――
[Table 26]

――――――――――――――――――――――――――――――――――――
No. R ³ A ⁵ G ₁ G ₂ G ₃ G ₄ n mp
――――――――――――――――――――――――――――――――――――
1-13-001a CF ₃ N CH CH C-CF ₃ CH 2 243-245
1-13-001b CF ₃ N CH CH C-CF ₃ CH 0 150-160
――――――――――――――――――――――――――――――――――――
[Table 27]

――――――――――――――――――――――――――――――――――――――
No. R ³ R ⁴ A ^1a G ₁ G ₂ G ₃ G ₄ n mp
――――――――――――――――――――――――――――――――――――――
1-14-001a CF ₃ H Me CH CH C-CF ₃ CH 2 *5
1-14-002a SOCF ₃ H Me CH CH C-CF ₃ CH 2 218-220
――――――――――――――――――――――――――――――――――――――
[Table 28]

――――――――――――――――――――――――――――――――――――――
No. R ² R ³ R ⁴ R ⁵ A ^1a Y2 Y3 n mp
――――――――――――――――――――――――――――――――――――――
1-15-001b H CF ₃ H Br HH CF ₃ 0 139-145
1-15-002a Br H CF ₃ H Me H CF ₃ 2 236-239
1-15-002b Br H CF ₃ H Me H CF ₃ 0 205-208
1-15-003a H CF ₃ H Br Me H CF ₃ 2 206-209
1-15-004a H SCF ₃ HH Me CF ₃ H 2 217-218
1-15-005a H SOCF ₃ HH Me CF ₃ H 2 267-269
1-15-006a H SO ₂ CF ₃ HH Me CF ₃ H 2 245-246
1-15-007a H CF ₃ H H Me HI 2 260-261
――――――――――――――――――――――――――――――――――――――
[Table 29]

――――――――――――――――――――――――――――――――――――――
No. R ³ A ^1a G ₁ G ₂ G ₃ G ₄ n mp
――――――――――――――――――――――――――――――――――――――
1-16-001a CF ₃ Me CH C-CF ₃ CH CH 2 274-276
1-16-001b CF ₃ Me CH C-CF ₃ CH CH 0 240-242
――――――――――――――――――――――――――――――――――――――
[Table 30]

――――――――――――――――――――――――――――――――――――――
No. R ³ R ⁴ R ⁶ G ₁ G ₂ G ₃ G ₄ n mp
――――――――――――――――――――――――――――――――――――――
1-17-001a H CF ₃ Br CH CI CH CH 2 255-260
――――――――――――――――――――――――――――――――――――――
[Table 31]

――――――――――――――――――――――――――――――――――
No. R ³ A ^1a G ₅ Y6 n mp
――――――――――――――――――――――――――――――――――
2-1-001a CF ₃ Me CH CF ₃ 2 249-251
2-1-001b CF ₃ Me CH CF ₃ 0 200-203
2-1-002a CF ₃ Me N CF ₃ 2 231-234
2-1-002b CF ₃ Me N CF ₃ 0 *1
2-1-003a CF ₃ Me CH Br 2 220-226
2-1-003b CF ₃ Me CH Br 0 191-195
2-1-004a CF ₃ Me CH Z6 2 279-282
――――――――――――――――――――――――――――――――――
[Table 32]

―――――――――――――――――――――――――――――――――――――――
No. R ³ A ^1a T ₁ G ₁ G ₂ G ₃ G ₄ n mp
―――――――――――――――――――――――――――――――――――――――
3-1-001a CF ₃ Me N-Me CH C-CF ₃ CH CH 2 143-146
3-1-001b CF ₃ Me N-Me CH C-CF ₃ CH CH 0 153-155
3-1-001c CF ₃ Me N-Me CH C-CF ₃ CH CH 1 123-126
3-1-002a CF ₃ Me S CH C-CF ₃ CH CH 2 70-75
3-1-002b CF ₃ Me S CH C-CF ₃ CH CH 0 120-122
3-1-002c CF ₃ Me S CH C-CF ₃ CH CH 1 195-197
―――――――――――――――――――――――――――――――――――――――
[Table 33]

―――――――――――――――――――――――――――――――――――――
No. J ₁ G ₁ G ₂ G ₃ G ₄ n mp
―――――――――――――――――――――――――――――――――――――
i-1-001 Et CH C-CF ₃ CH CH 0 76-78
i-1-002 H CH C-CF ₃ CH CH 0 200-201
i-1-003 Et CH CH C-CF ₃ CH 0 50-52
i-1-004 H CH CH C-CF ₃ CH 0 163-171
i-1-005 Et CH C-Cl CH CH 0 63-64
i-1-006 H CH C-Cl CH CH 0 178-170
i-1-007 Et CH CF CH CH 0 30-31
i-1-008 H CH CF CH CH 0 165-168
i-1-009 Et CH CI CH CH 0 110-112
i-1-010 H CH CI CH CH 0 214-215
i-1-011 H CH C-Br CH CH 0 170-173
i-1-012 Et CH C-OMe CH CH 0 *2
i-1-013 H CH C-OMe CH CH 0 180-182
i-1-014 Et CH C-NO ₂ CH CH 0 95-97
i-1-015 H CH C-NO ₂ CH CH 0 188-190
i-1-016 Et CH CH C-Cl CH 0 70-71
i-1-017 H CH CH C-Cl CH 0 210-212
i-1-018 Et CH CH CF CH 0 74-76
i-1-019 H CH CH CF CH 0 243-244
i-1-020 Et CH CH CI CH 0 *2
i-1-021 H CH CH CI CH 0 175-178
i-1-022 H CH CH C-Br CH 0 150-152
i-1-023 Et CH C-CF ₃ CH C-Cl 0 138-140
i-1-024 H CH CI C-Cl CH 0 212-220
i-1-025 Et CH CI CH C-Cl 0 *2
i-1-026 Et CH CI CH CF 0 173-175
i-1-027 H CH CI CH CF 0 189-190
i-1-028 H CH C-CF ₃ N CH 0 175-178
i-1-029 Et CH CH C-CF ₃ CH 2 129-131
i-1-030 H CH CH C-CF ₃ CH 2 158-160
i-1-031 H CH CH C-NO ₂ CH 2 234-235
i-1-032 Et CH CH C-CN CH 0 *1
i-1-033 Et CH CH CI CH 2 *1
i-1-034 H CH CH CI CH 2 *1
i-1-035 Et CH CH C-NH ₂ CH 2 *1
i-1-036 Et CH CH C-NH ₂ CH 0 *2
i-1-037 H CH CH C-NH ₂ CH 2 *1
i-1-038 Et CH CH C-NHAc CH 2 *1
―――――――――――――――――――――――――――――――――――――
[Table 34]

―――――――――――――――――――――――――――――
No. J ₁ G ₅ Y6 n mp
―――――――――――――――――――――――――――――
i-2-001 Et CH CF ₃ 0 41-43
i-2-002 H CH CF ₃ 0 176-178
―――――――――――――――――――――――――――――
[Table 35]

―――――――――――――――――――――――――――――――――――
No. R ³ J ₂ G ₁ G ₂ G ₃ G ₄ mp
―――――――――――――――――――――――――――――――――――
i-3-001 CF ₃ H CH C-Br C-CF ₃ CH 220-225
i-3-002 CF ₃ H C-Me CH C-Me CH 219-221
i-3-003 CF ₃ H C-CF ₃ CH CH CH 180-183
i-3-004 CF ₃ H CH C-CF ₂ CF ₃ CH CH 208-210
i-3-005 CF ₃ H CH C-Cl C-Cl CH 245-248
i-3-006 CF ₃ I CH C-Cl C-Cl CH *5
i-3-007 CF ₃ H CH CI C-Me CH >250
i-3-008 CF ₃ Cl CH CI C-Me CH >250
i-3-009 CF ₃ H CH CI C-CF ₃ CH 180-184
i-3-010 CF ₃ H CH CI C-CN CH 284-285
i-3-011 CF ₃ H CH CI CF CH >250
i-3-012 CF ₃ H CH CI C-OMe CH >300
i-3-013 CF ₃ H CH C-Cl CH C-Me 237-239
i-3-014 CF ₃ H CH C-Cl CH C-Cl 265-266
i-3-015 CF ₃ H CH CF CH CF >250
i-3-016 CF ₃ Cl CH CF CH CF 239-242
i-3-017 CF ₃ H CH CI CH CI >300
i-3-018 CF ₃ H CH C-Br CH CF >300
i-3-019 CF ₃ Cl CH C-Br CH CF 244-246
i-3-020 CF ₃ H CH CI CH C-CN 284-285
i-3-021 CF ₃ H CH C-Cl CH C-CF ₃ 252-257
i-3-022 CF ₃ H CH C-CF ₃ CH CF 288-289
i-3-023 CF ₃ Cl CH C-CF ₃ CH CF 255-256
i-3-024 CF ₃ H CH C-CF ₃ CH CI >250
i-3-025 CF ₃ H CH CI CH C-Me 257-260
i-3-026 CF ₃ H CH C-Me CH C-Cl >250
i-3-027 CF ₃ Cl CH C-Me CH C-Cl *5
i-3-028 CF ₃ H CH CI CH CF >250
i-3-029 CF ₃ H CH CH CH C-CF ₃ 198-201
i-3-030 CF ₃ H CH C-Cl C-Cl C-Cl *5
i-3-031 CF ₃ Cl CH C-Cl C-Cl C-Cl >250
i-3-032 CF ₃ H CH CH C-NO ₂ CH 150-151
i-3-033 CF ₃ H CH CI CH N 280-285
i-3-034 CF ₃ Cl CH CI CH N 250-255
i-3-035 CF ₃ H CH C-CF ₃ CH N 283-285
i-3-036 CF ₃ I CH C-CF ₃ CH N 260-265
i-3-037 CF ₃ H CH N C-CF ₃ CH 257-260
i-3-038 CF ₃ Br CH N C-CF ₃ CH 254-259
i-3-039 CF ₃ H CH CI N CH 256-259
i-3-040 CF ₃ H CH CH CI CH 240-242
i-3-041 CF ₃ H CH CH C-CO ₂ Me CH *1
i-3-042 CF ₃ H CH CH C-CO ₂ H CH *1
i-3-043 CF ₃ H CH CH CH CH *1
i-3-044 CF ₃ H CH CH C-NH ₂ CH >300
i-3-045 CF ₃ H CH CH CH C-NH ₂ *1
i-3-046 CF ₃ H CH CH CI C-NH ₂ *1
i-3-047 CF ₃ H CH CH C-NHAc CH 253-254
i-3-048 CF ₃ H CH CH C-CONH ₂ CH *1
―――――――――――――――――――――――――――――――――――
[Table 36]

―――――――――――――――――――――――――――――――――――――
No. R ³ J ₃ T ₁ G ₁ G ₂ G ₃ G ₄ mp
―――――――――――――――――――――――――――――――――――――
i-4-001 CF ₃ H N-Me CH C-CF ₃ CH CH 200-202
i-4-002 CF ₃ I N-Me CH C-CF ₃ CH CH 165-167
i-4-003 CF ₃ HS CH C-CF ₃ CH CH 191-193
i-4-004 CF ₃ Cl S CH C-CF ₃ CH CH 158-160
―――――――――――――――――――――――――――――――――――――
[Table 37]

―――――――――――――――――――――――――――――――――――――
No. R ³ A _1a A ⁴ A ⁵ Y1 Y2 Y3 Y4 n mp
―――――――――――――――――――――――――――――――――――――
i-5-001 CF ₃ Me CH NHIH Cl 0 208-217
i-5-002 CF ₃ Me CH NHIH OEt 2 230-239
i-5-003 CF ₃ Me CH NHH CF ₃ H 0 135-140
i-5-004 I Me CH NHH CF ₃ H 0 194-195
i-5-005 CF ₃ Me CH N CF ₃ HHH 0 *2
i-5-006 CF ₃ Me CH NHIHH 0 90-92
i-5-007 CF ₃ Me CH NHI Cl H 0 203-205
i-5-008 H Me CH NHH CF ₃ H 0 125-127
i-5-009 CF ₃ H CH C-Br HH CF ₃ H 0 70-72
i-5-010 Cl Me CH NH CF ₃ HH 0 75-80
―――――――――――――――――――――――――――――――――――――
[Table 38]

―――――――――――――――――――――――――――――――――――――
No. J ₄ R ⁶ G ₁ G ₂ G ₃ G ₄ n mp
―――――――――――――――――――――――――――――――――――――
i-6-001 HH CH CH C-CF ₃ CH 0 60-64
i-6-002 HH CH CH C-CF ₃ CH 2 135-138
i-6-003 Br H CH CH C-CF ₃ CH 2 122-123
i-6-004 HH CH C-CF ₃ CH CH 0 73-75
i-6-005 HH CH C-CF ₃ CH CH 2 125-127
i-6-006 Br H CH C-CF ₃ CH CH 2 83-85
i-6-007 HH CH CI CH CH 0 147-149
i-6-008 HH CH CI CH CH 2 110-133
i-6-009 Br H CH CI CH CH 2 162-164
i-6-010 H Me CH C-CF ₃ CH CH 0 115-117
i-6-011 H Me CH C-CF ₃ CH CH 2 141-143
i-6-012 Br Me CH C-CF ₃ CH CH 2 145-147
―――――――――――――――――――――――――――――――――――――
[Table 39]

――――――――――――――――――――――――――――――――――
No. G ₁ G ₂ G ₃ G ₄ n mp
――――――――――――――――――――――――――――――――――
i-7-001 CH CH C-CF ₃ CH 0 *2
i-7-002 CH CI CH CH 0 123-129
i-7-003 CH CH CI CH 0 *2
i-7-004 CH C-CF ₃ CH CH 0 *2
i-7-005 CH C-Br CH CF 0 *2
i-7-006 CH CI CH CF 0 150-153
i-7-007 CH C-Br CH CH 0 88-92
――――――――――――――――――――――――――――――――――
[Table 40]

―――――――――――――――――――――――――――――――――
No. R ³ A ⁴ A ⁵ J ₅ J ₆ mp
―――――――――――――――――――――――――――――――――
i-8-001 CF ₃ CH NHH 106-108
i-8-002 CF ₃ CH N Br H 90-91
i-8-003 CF ₃ CH N SEt H 67-69
i-8-004 CF ₃ CH N SEt Br *2
i-8-005 CF ₃ N CH HH 136-140
i-8-006 CF ₃ N CH Br H 127-131
i-8-007 CF ₃ N CH SEt H 90-93
i-8-008 CF ₃ N CH SEt Br *2
i-8-009 SCF ₃ CH NHH 161-162
i-8-010 SCF ₃ CH N Br H 119-121
i-8-011 SCF ₃ CH N SEt H 104-106
i-8-012 SCF ₃ CH N SEt Br *2
i-8-013 SOCF ₃ CH NHH 117-119
i-8-014 SOCF ₃ CH N Br H *2
i-8-015 SOCF ₃ CH N SEt H *2
i-8-016 SOCF ₃ CH N SEt Br *2
―――――――――――――――――――――――――――――――――
Table 41 shows ¹ H-NMR data of the compound of the present invention and the production intermediate. The proton nuclear magnetic resonance chemical shift value was measured at 300 MHz (model: ECX300 or ECP300, manufactured by JEOL) in deuterated chloroform solvent using Me ₄ Si (tetramethylsilane) as a reference substance. However, No.i-3-042 and No.i-3-048 were measured in a heavy dimethyl sulfoxide solvent, and No.i-1-037 was measured in a heavy water solvent.

The symbols in the proton nuclear magnetic resonance chemical shift values have the following meanings.
s: singlet, brs: broad singlet, d: doublet, dd: double doublet, t: triplet, q: quartet, m: multiplet [Table 41].
――――――――――――――――――――――――――――――――――――――――
No. ¹ H NMR (CDCl ₃ , Me ₄ Si, 300MHz).
――――――――――――――――――――――――――――――――――――――――
1-1-001a δ 9.68-9.63(m, 1H), 8.76(s, 1H), 8.35(s, 1H), 7.95(d, J=9.5Hz, 1H), 7.71(d, J=9.5Hz, 1H), 4.17(s, 3H), 4.12(q, J=7.2Hz, 2H), 1.26(t, J=7.2Hz, 3H).
1-1-001b δ 9.05-8.95(m, 1H), 8.72(s, 1H), 8.40(s, 1H), 7.82(d, J=9.7Hz, 1H), 7.52(dd, J=9.7, 1.9 Hz, 1H), 4.31(s, 3H), 3.14(q, J=7.4Hz, 2H), 1.22(t, J=7.4Hz, 3H).
1-1-001c δ9.95-9.90(m, 1H), 8.72(d, J=1.4Hz, 1H), 8.31(d, J=1.4Hz, 1H), 7.86(d, J=9.5Hz, 1H) , 7.57(dd, J=9.5, 2.0Hz, 1H), 4.44(s, 3H), 3.80-3.50(m, 2H), 1.57(t, J=7.5Hz, 3H).
1-1-003a δ9.32(s, 1H), 8.75(d, J=1.2Hz, 1H), 8.35(d, J=1.2Hz, 1H), 7.79(d, J=9.6Hz, 1H), 7.54(dd, J=9.6Hz, 1.8Hz, 1H), 4.15(s, 3H), 4.04(q, J=7.5Hz, 2H), 1.46(t, J=7.5Hz, 3H).
1-1-003b δ8.71(s, 1H), 8.68(d, J=1.2Hz, 1H), 8.39(s, 1H), 7.66(d, J=9.6Hz, 1H), 7.35(d, J =9.6Hz, 1.8Hz, 1H), 4.29(s, 3H), 3.09(q, J=7.5Hz, 2H), 1.21(t, J=7.5Hz, 3H).
1-1-003c δ9.53(d, J=1.2Hz, 1H), 8.71(d, J=1.2Hz, 1H), 8.30(d, J=1.2Hz, 1H), 7.70(d, J=9.6 Hz, 1H), 7.40(dd, J=9.6, 1.8Hz, 1H), 4.41(s, 3H), 3.80-3.50(m, 2H), 1.56(t, J=7.5Hz, 3H).
1-1-004a δ9.26-9.22(m, 1H), 8.74(d, J=1.4Hz, 1H), 8.33(d, J=1.4Hz, 1H), 7.85-7.78(m, 1H), 7.57 -7.44(m, 1H), 4.15(s, 3H), 4.04(q, J=7.5Hz, 2H), 1.45(t, J=7.5Hz, 3H).
1-1-004b δ8.70(d, J=1.2Hz, 1H), 8.60-8.55(m, 1H), 8.37(d, J=1.2Hz, 1H), 7.73-7.65(m, 1H), 7.35 -7.25(m, 1H), 4.29(s, 3H), 3.09(q, J=7.4Hz, 2H), 1.20(t, J=7.4Hz, 3H).
1-1-004c δ9.47-9.43(m, 1H), 8.71(dd, J=1.8, 0.6Hz, 1H), 8.30(d, J=1.7Hz, 1H), 7.77-7.70(m, 1H) , 7.40-7.32(m, 1H), 4.42(s, 3H), 3.80-3.45(m, 2H), 1.55(t, J=7.5Hz, 3H).
1-1-005a δ9.49(s, 1H), 8.75(s, 1H), 8.35(s, 1H), 7.75(dd, J=9.3, 1.2Hz, 1H), 7.61(d, J=9.3Hz , 1H), 4.13(s, 3H), 4.01(q, J=7.2Hz, 2H), 1.46(t, J=7.2Hz, 3H).
1-1-005b δ8.91-8.88(m, 1H), 8.73-8.70(m, 1H), 8.41-8.39(m, 1H), 7.56(dd, J=9.3, 1.8Hz, 1H), 7.50( d, J=9.3Hz, 1H), 4.29(s, 3H), 3.08(q, J=7.2Hz, 2H), 1.21(t, J=7.2Hz, 3H).
1-1-005c δ9.72(s, 1H), 8.71(d, J=1.2Hz, 1H), 8.30(d, J=1.2Hz, 1H), 7.61(d, J=9.6Hz, 1H), 7.54(d, J=9.6Hz, 1H), 4.41(s, 3H), 3.75-3.49(m, 2H), 1.56(t, J=7.5Hz, 3H).
1-1-006a δ9.41(s, 1H), 8.75(s, 1H), 8.34(s, 1H), 7.72(d, J=9.6Hz, 1H), 7.64(dd, J=9.6, 1.8Hz , 1H), 4.14(s, 3H), 4.04(q, J=7.5Hz, 2H), 1.46(t, J=7.5Hz, 3H).
1-1-006b δ8.78(s, 1H), 8.71(s, 1H), 8.42-8.35(m, 1H), 7.70-7.55(m, 1H), 7.50-7.40(m, 1H), 4.29( s, 3H), 3.09(q, J=7.5Hz, 2H), 1.21(t, J=7.5Hz, 3H).
1-1-007a δ8.80(d, J=2.1Hz, 1H), 8.73(s, 1H), 8.33(d, J=0.9Hz, 1H), 7.70(d, J=9.9Hz, 1H), 7.33(dd, J=9.9, 2.1Hz, 1H), 4.12(s, 3H), 3.99(q, J=7.2Hz, 2H), 3.93(s, 3H), 1.44(t, J=7.2Hz, 3H ).
1-1-007b δ8.72-8.68(m, 1H), 8.37(d, J=2.1Hz, 1H), 8.16(d, J=2.1Hz, 1H), 7.60(d, J=9.6Hz, 1H ), 7.16(dd, J=9.6, 2.1Hz, 1H), 4.29(s, 3H), 3.94(s, 3H), 3.06(q, J=7.2Hz, 2H), 1.20(t, J=7.2Hz , 3H).
1-1-008a δ 10.34(dd, J=2.1, 0.6Hz, 1H), 8.77(d, J=1.2Hz, 1H), 8.36(d, J=1.2Hz, 1H), 8.33(dd, J =9.9, 2.1Hz, 1H), 7.93(dd, J=9.9, 0.6Hz, 1H), 4.20(s, 3H), 4.16(q, J=7.2Hz, 2H), 1.50(t, J=7.2Hz , 3H).
1-1-008b δ9.73(d, J=2.4Hz, 1H), 8.73(d, J=2.4Hz, 1H), 8.40(d, J=2.4Hz, 1H), 8.14(dd, J=9.9 , 2.4Hz, 1H), 7.79(d, J=9.9Hz, 1H), 4.33(s, 3H), 3.20(q, J=7.2Hz, 2H), 1.25(t, J=7.2Hz, 3H).
1-1-009a δ9.00(s, 1H), 8.74(d, J=1.2Hz, 1H), 8.33(d, J=1.2Hz, 1H), 7.73(d, J=9.3Hz, 1H), 7.42(dd, J=9.3, 1.2Hz, 1H), 4.11(s, 3H), 3.94(q, J=7.5Hz, 2H), 2.47(s, 3H), 1.44(t, J=7.5Hz, 3H ).
1-1-010a δ9.26(d, J=1.2Hz, 1H), 8.74(d, J=1.5Hz, 1H), 8.33(d, J=1.5Hz, 1H), 7.76(d, J=9.0 Hz, 1H), 7.60(dd, J=9.0, 1.8Hz, 1H), 4.14(s, 3H), 4.07-3.96(m, 4H), 3.23(t, J=7.2Hz, 2H), 2.69(t , J=7.2Hz, 2H), 1.65-1.22(m, 12H), 0.90(t, J=7.5Hz, 6H).
1-1-011a δ9.61(s, 1H), 8.75(d, J=1.2Hz, 1H), 8.35(d, J=1.2Hz, 1H), 7.87(dd, J=9.6, 0.9Hz, 1H ), 7.74(dd, J=9.6, 1.2Hz, 1H), 4.17(s, 3H), 4.08(q, J=7.5Hz, 2H), 1.46(t, J=7.5Hz, 3H).
1-1-012a δ9.24(d, J=7.2Hz, 1H), 8.75(d, J=1.4Hz, 1H), 8.35(d, J=1.4Hz, 1H), 7.84(d, J=9.2 Hz, 1H), 7.62-7.54(m, 1H), 7.21-7.13(m, 1H), 4.15(s, 3H), 3.99(q, J=7.4Hz, 2H), 1.45(t, J=7.4Hz , 3H).
1-1-012b δ8.71(s, 1H), 8.66(d, J=6.8Hz, 1H), 8.39(s, 1H), 7.72(d, J=8.9Hz, 1H), 7.43-7.35(m , 1H), 7.08-7.01(m, 1H), 4.31(s, 3H), 3.06(q, J=7.4Hz, 2H), 1.20(t, J=7.4Hz, 3H).
1-1-013a δ9.18(d, J=7.4Hz, 1H), 8.74(s, 1H), 8.33(d, J=1.2Hz, 1H), 7.85-7.80(m, 1H), 7.15-7.10 (m, 1H), 4.14(s, 3H), 4.03(q, J=7.4Hz, 2H), 1.43(t, J=7.4Hz, 3H).
1-1-013b δ8.70(d, J=1.6Hz, 1H), 8.57(d, J=7.4Hz, 1H), 8.37(s, 1H), 7.71(d, J=1.6Hz, 1H), 7.02(dd, J=7.4, 1.6Hz, 1H), 4.28(s, 3H), 3.07(q, J=7.5Hz, 2H), 1.19(t, J=7.5Hz, 3H).
1-1-013c δ9.40(dd, J=7.4, 0.8Hz, 1H), 8.75-8.65(m, 1H), 8.35-8.25(m, 1H), 7.76(dd, J=2.2, 0.8Hz, 1H), 6.97(dd.J=7.4, 2.2Hz, 1H), 4.41(s, 3H), 3.75-3.45(m, 2H), 1.53(t, J=7.4Hz, 3H).
1-1-014a δ9.27-9.22(m, 1H), 8.75-8.73(m, 1H), 8.35-8.32(m, 1H), 7.48-7.42(m, 1H), 7.07-6.99(m, 1H ), 4.14(s, 3H), 4.02(q, J=7.4Hz, 2H), 1.44(t, J=7.4Hz, 3H).
1-1-014b δ8.70(dd, J=2.0, 1.2Hz, 1H), 8.66-8.58(m, 1H), 8.37(d, J=1.2Hz, 1H), 7.34(dd, J=8.9, 2.4Hz, 1H), 6.95-6.87(m, 1H), 4.28(s, 3H), 3.06(q, J=7.4Hz, 2H), 1.19(t, J=7.4Hz, 3H).
1-1-014c δ9.50-9.43(m, 1H), 8.73-8.69(m, 1H), 8.30(d, J=1.4Hz, 1H), 7.38(dd, J=9.2, 2.4Hz, 1H) , 6.93-6.83(m, 1H), 4.41(s, 3H), 3.75-3.45(m, 2H), 1.54(t, J=7.3Hz, 3H).
1-1-015a δ8.99(dd, J=7.5, 0.6Hz, 1H), 8.75(d, J=1.2Hz, 1H), 8.33(d, J=1.2Hz, 1H), 8.30-8.26(m , 1H), 7.38(dd, J=7.2, 1.2Hz, 1H), 4.13(s, 3H), 4.02(q, J=7.5Hz, 2H), 1.43(t, J=7.5Hz, 3H).
1-1-015b δ8.87(d, J=1.2Hz, 1H), 8.82(s, 1H), 8.48(s, 1H), 8.41(d, J=7.2Hz, 1H), 7.51(d, J =7.2Hz, 1H), 4.38(s, 3H), 3.14(q, J=7.5Hz, 2H), 1.25(t, J=7.5Hz, 3H).
1-1-016a δ9.11(dd, J=7.5, 0.9Hz, 1H), 8.75-8.72(m, 1H), 8.33(d, J=1.2Hz, 1H), 8.02-8.00(m, 1H) , 7.24-7.22(m, 1H), 4.14(s, 3H), 4.03(q, J=7.5Hz, 2H), 1.43(t, J=7.5Hz, 3H).
1-1-016b δ8.71(s, 1H), 8.52(d, J=7.5Hz, 1H), 8.39(s, 1H), 7.93-7.89(m, 1H), 7.13(dd, J=7.5, 1.8Hz, 1H), 4.29(s, 3H), 3.07(q, J=7.5Hz, 2H), 1.19(t, J=7.5Hz, 3H).
1-1-016c δ9.35(d, J=7.5Hz, 1H), 8.72(s, 1H), 8.31(d, J=2.1Hz, 1H), 7.96(dd, J=2.1, 0.6Hz, 1H ), 7.09(dd, J=7.5Hz, 2.1Hz, 1H), 4.41(s, 3H), 3.75-3.45(m, 2H), 1.53(t, J=7.5Hz, 3H).
1-1-017a δ9.08(d, J=7.2Hz, 1H), 8.74(d, J=1.5Hz, 1H), 8.33(d, J=1.5Hz, 1H), 7.59(s, 1H), 6.99(dd, J=7.2, 1.8Hz, 1H), 4.12(s, 3H), 3.95(q, J=7.5Hz, 2H), 2.53(s, 3H), 1.42(t, J=7.5Hz, 3H ).
1-1-018a δ9.41(dd, J=7.5, 0.9Hz, 1H), 8.77(d, J=0.9Hz, 1H), 8.36(d, J=0.9Hz, 1H), 8.25-8.22(m , 1H), 7.29(dd, J=7.5, 1.5Hz, 1H), 4.19(s, 3H), 4.14(q, J=7.5Hz, 2H), 1.46(t, J=7.5Hz, 3H).
1-1-020a δ9.61-9.59(m, 1H), 8.78-8.75(m, 1H), 8.35(d, J=1.5Hz, 1H), 7.78(d, J=1.5Hz, 1H), 4.22 (s, 3H), 4.14(q, J=7.4Hz, 2H), 1.47(t, J=7.4Hz, 3H).
1-1-020b δ8.95(d, J=1.4Hz, 1H), 8.73(d, J=2.0Hz, 1H), 8.39(d, J=2.0Hz, 1H), 7.60(d, J=1.4 Hz, 1H), 4.36(s, 3H), 3.18(q, J=7.4Hz, 2H), 1.23(t, J=7.4Hz, 3H).
1-1-021b δ8.82-8.76(m, 1H), 8.71(d, J=2.0Hz, 1H), 8.38(d, J=2.0Hz, 1H), 7.19(d, J=1.4Hz, 1H ), 4.35(s, 3H), 3.24(q, J=7.4Hz, 2H), 3.15(qJ=7.4Hz, 2H), 1.49(t, J=7.4Hz, 3H), 1.22(t, J=7.4 Hz, 3H).
1-1-022a δ9.92-9.87(m, 1H), 8.79(d, J=2.0Hz, 1H), 8.44(d, J=2.0Hz, 1H), 8.37(d, J=1.2Hz, 1H ), 4.22(s, 3H), 4.22(q, J=7.4Hz, 2H), 3.79(q, J=7.5Hz, 2H), 1.50(t, J=7.4Hz, 3H), 1.40(t, J =7.5Hz, 3H).
1-1-023c δ9.85(s, 1H), 8.74(d, J=1.4Hz, 1H), 8.32(d, J=1.4Hz, 1H), 8.17(s, 1H), 4.44(s, 3H ), 3.82-3.51(m, 2H), 1.58(t, J=7.3Hz, 3H).
1-1-024a δ9.16(s, 1H), 8.76(d, J=1.2Hz, 1H), 8.35(d, J=1.2Hz, 1H), 8.14(s, 1H), 4.15(s, 3H ), 4.07(q, J=7.5Hz, 2H), 2.57(s, 3H), 1.46(t, J=7.5Hz, 3H).
1-1-025b δ8.71(d, J=1.5Hz, 1H), 8.37(d, J=1.5Hz, 1H), 7.38(s, 1H), 6.55(s, 1H), 4.13(s, 3H ), 3.15(s, 3H), 2.91(q, J=7.5Hz, 2H), 2.41(s, 3H), 1.11(t, J=7.5Hz, 3H).
1-1-025c δ8.74-8.72(m, 1H), 8.34(d, J=1.2Hz, 1H), 7.45(s, 1H), 6.75(s, 1H), 4.10(s, 3H), 3.88 -3.72(m, 1H), 3.67-3.52(m, 1H), 3.02(s, 3H), 2.48(s, 3H), 1.42(t, J=7.5Hz, 3H).
1-1-026a δ9.41(d, J=7.5Hz, 1H), 8.66(d, J=1.7Hz, 1H), 8.43(d, J=1.7Hz, 1H), 8.16-8.12(m, 1H ), 7.31(dd, J=7.5, 1.7Hz, 1H), 4.12(s, 3H), 4.10(q, J=7.4Hz, 2H), 1.45(t, J=7.4Hz, 3H).
1-1-030a δ9.42(d, J=7.3Hz, 1H), 8.22(d, J=7.8Hz, 1H), 8.17(s, 1H), 7.70(d, J=7.8Hz, 1H), 7.32(dd, J=7.3, 1.9Hz, 1H), 4.19(s, 3H), 4.11(q, J=7.4Hz, 2H), 1.46(t, J=7.4Hz, 3H).
1-1-030c δ9.63(d, J=7.5Hz, 1H), 8.18(d, J=8.5Hz, 1H), 8.10(s, 1H), 7.68(d, J=8.5Hz, 1H), 7.16(dd, J=7.5, 1.7Hz, 1H), 4.45(s, 3H), 3.81-3.45(m, 2H), 1.56(t, J=7.5Hz, 3H).
1-1-032a δ9.40(d, J=7.5Hz, 1H), 8.77-8.74(m, 1H), 8.35(d, J=1.8Hz, 1H), 8.18-8.14(m, 1H), 7.32 (dd, J=7.5, 1.8Hz, 1H), 4.71(q, J=7.5Hz, 2H), 4.09(q, J=7.5Hz, 2H), 1.50(t, J=7.5Hz, 3H), 1.46 (t, J=7.5Hz, 3H).
1-1-032b δ8.77(d, J=7.5Hz, 1H), 8.73-8.70(m, 1H), 8.42-8.38(d, J=1.8Hz, 1H), 8.07-8.03(m, 1H) , 7.20(dd, J=7.5, 1.5Hz, 1H), 4.96(q, J=7.5Hz, 2H), 3.13(q, J=7.5Hz, 2H), 1.50(t, J=7.5Hz, 3H) , 1.20(t, J=7.5Hz, 3H).
1-1-033a δ9.29(dd, J=7.2, 1.2Hz, 1H), 8.77-8.72(m, 1H), 8.53-8.48(m, 1H), 8.36-8.32(m, 1H), 7.71( dd, J=7.2, 1.8Hz, 1H), 4.17(s, 3H), 4.06(q, J=7.5Hz, 2H), 4.03(s, 3H), 1.45(t, J=7.5Hz, 3H).
1-1-034a δ9.30(dd, J=7.5, 1.2Hz, 1H), 8.78-8.74(m, 1H), 8.55-8.50(m, 1H), 8.36-8.34(m, 1H), 7.72( dd, J=7.5, 1.8Hz, 1H), 4.49(q, J=7.5Hz, 2H), 4.17(s, 3H), 4.07(q, J=7.5Hz, 2H), 1.47(t, J=7.5 Hz, 3H), 1.45(t, J=7.5Hz, 3H).
1-1-035a δ9.27(dd, J=7.5, 0.9Hz, 1H), 8.77-8.74(m, 1H), 8.36-8.32(m, 1H), 7.86-7.83(m, 1H), 7.22( dd, J=7.5, 1.8Hz, 1H), 4.15(s, 3H), 4.03(q, J=7.5Hz, 2H), 3.18(s, 3H), 3.13(s, 3H), 1.44(t, J =7.5Hz, 3H).
1-1-036a δ9.26(s, 1H), 8.77(d, J=1.4Hz, 1H), 8.36(d, J=1.4Hz, 1H), 8.17(s, 1H), 4.18(s, 3H ), 4.14(q, J=7.5Hz, 2H), 2.63(s, 3H), 1.48(t, J=7.5Hz, 3H).
1-1-037a δ9.46(s, 1H), 8.76(d, J=1.2Hz, 1H), 8.36(d, J=1.2Hz, 1H), 8.19(s, 1H), 4.18(s, 3H ), 4.13(q, J=7.4Hz, 2H), 4.03(dd, J=5.7, 2.0Hz, 2H), 3.25(t, J=7.0Hz, 2H), 2.73(t, J=7.0Hz, 2H) ), 1.48(t, J=7.4Hz, 3H), 1.42-1.23(m, 9H), 0.89(t, J=7.4Hz, 6H).
1-1-038a δ 10.24(s, 1H), 8.80(s, 1H), 8.39(s, 1H), 8.36(s, 1H), 4.23(s, 3H), 4.20(q, J=7.5Hz , 2H), 3.36(s, 3H), 1.52(t, J=7.5Hz, 3H).
1-1-039a δ 10.02(s, 1H), 8.78(d, J=1.4Hz, 1H), 8.38(s, 1H), 8.23(s, 1H), 4.30-3.97(m, 2H), 4.20 (s, 3H), 2.98(s, 3H), 1.51(t, J=7.5Hz, 3H).
1-1-040a δ8.77(s, 1H), 8.34(s, 1H), 8.07(dd, J=7.7, 2.6Hz, 1H), 7.74-7.65(m, 2H), 4.11(s, 3H) , 4.03(q, J=7.5Hz, 2H), 1.51(t, J=7.5Hz, 3H).
1-1-040b δ8.76-8.73(m, 1H), 8.42-8.37(m, 1H), 7.96(d, J=9.2Hz, 1H), 7.59(d, J=7.5Hz, 1H), 7.47 -7.38(m, 1H), 4.15(s, 3H), 2.95(q, J=7.4Hz, 2H), 1.11(t, J=7.4Hz, 3H).
1-1-040c δ8.74(d, J=1.4Hz, 1H), 8.36(d, J=1.4Hz, 1H), 8.05(d, J=8.5Hz, 1H), 7.64(d, J=7.5 Hz, 1H), 7.59-7.52(m, 1H), 4.61-4.48(m, 1H), 3.95(s, 3H), 3.41-3.26(m, 1H), 1.48(t, J=7.5Hz, 3H) .
1-1-041a δ9.04(d, J=7.5Hz, 1H), 8.74(s, 1H), 8.33(s, 1H), 7.52(d, J=1.5Hz, 1H), 6.97(dd, J =7.5, 1.5Hz, 1H), 4.13(s, 3H), 4.06(dd, J=5.7, 2.0Hz, 2H), 3.99(q, J=7.5Hz, 2H), 3.36(t, J=7.2Hz , 2H), 2.80(t, J=7.2Hz, 2H), 1.49-1.22(m, 12H), 0.89(t, J=7.5Hz, 6H).
1-1-042a δ9.02(d, J=7.5Hz, 1H), 8.76-8.73(m, 1H), 8.35-8.32(m, 1H), 7.42-7.40(m, 1H), 6.97(dd, J=7.5, 2.1Hz, 1H), 4.13(s, 3H), 3.97(q, J=7.5Hz, 2H), 2.61(s, 3H), 1.42(t, J=7.5Hz, 3H).
1-1-043a δ9.41(dd, J=7.5, 0.6Hz, 1H), 8.76(d, J=1.5Hz, 1H), 8.35(d, J=1.8Hz, 1H), 8.21(d, J =1.8Hz, 1H), 7.29(dd, J=7.5, 1.8Hz, 1H), 4.18(s, 3H), 4.10(q, J=7.5Hz, 2H), 2.88(s, 3H), 1.46(t , J=7.5Hz, 3H).
1-1-044a δ9.49(dd, J=7.5, 1.2Hz, 1H), 8.77(d, J=1.5Hz, 1H), 8.50-8.46(m, 1H), 8.37-8.34(m, 1H) , 7.57(dd, J=7.5, 1.2Hz, 1H), 4.20(s, 3H), 4.14(q, J=7.5Hz, 2H), 3.20(s, 3H), 1.47(t, J=7.5Hz, 3H).
1-1-045a δ9.63(d, J=0.6Hz, 1H), 8.75-8.79(m, 1H), 8.38-8.35(m, 1H), 7.96(dd, J=9.3, 0.6Hz, 1H) , 7.69(dd, J=9.3, 1.2Hz, 1H), 4.18(s, 3H), 4.11(q, J=7.5Hz, 2H), 1.46(t, J=7.5Hz, 3H).
1-1-045b δ8.99(s, 1H), 8.73(d, J=0.6Hz, 1H), 8.40(d, J=1.2Hz, 1H), 7.83(d, J=9.3Hz, 1H), 7.50(d, J=9.3Hz, 1H), 4.32(s, 3H), 3.14(q, J=7.5Hz, 2H), 1.22(t, J=7.5Hz, 3H).
1-1-046a δ9.43(s, 1H), 8.77-8.74(m, 1H), 8.36-8.33(m, 1H), 7.96(s, 1H), 4.15(s, 3H), 4.08(q, J=7.4Hz, 2H), 1.46(t, J=7.4Hz, 3H).
1-1-047a δ9.64(s, 1H), 8.76(s, 1H), 8.35(s, 1H), 7.98(s, 1H), 4.15(s, 3H), 4.07(q, J=7.4Hz , 2H), 1.47(t, J=7.4Hz, 3H).
1-1-047b δ8.88(d, J=0.7Hz, 1H), 8.57(d, J=1.0Hz, 1H), 8.24(d, J=1.0Hz, 1H), 7.75(d, J=0.7 Hz, 1H), 4.15(s, 3H), 2.97(q, J=7.4Hz, 2H), 1.08(t, J=7.4Hz, 3H).
1-1-048a δ9.55(s, 1H), 8.75(d, J=1.0Hz, 1H), 8.34(d, J=1.0Hz, 1H), 7.71(s, 1H), 4.13(s, 3H ), 4.00(q, J=7.5Hz, 2H), 2.61(s, 3H), 1.45(t, J=7.5Hz, 3H).
1-1-048b δ8.96(s, 1H), 8.70(s, 1H), 8.38(s, 1H), 7.60(s, 1H), 4.28(s, 3H), 3.06(q, J=7.5Hz , 2H), 2.57(s, 3H), 1.20(t, J=7.5Hz, 3H).
1-1-049a δ9.76(s, 1H), 8.77(s, 1H), 8.36(s, 1H), 8.20(s, 1H), 4.17(s, 3H), 4.13(q, J=7.5Hz , 2H), 1.48(t, J=7.5Hz, 3H).
1-1-049b δ9.09(s, 1H), 8.72(s, 1H), 8.40(s, 1H), 8.09(s, 1H), 4.31(s, 3H), 3.16(q, J=7.5Hz , 2H), 1.23(t, J=7.5Hz, 3H).
1-1-050a δ9.70(s, 1H), 8.79-8.76(m, 1H), 8.38-8.35(m, 1H), 8.20(s, 1H), 4.18(s, 3H), 4.16(q, J=7.4Hz, 2H), 1.48(t, J=7.4Hz, 3H).
1-1-050b δ9.04(s, 1H), 8.76-8.73(m, 1H), 8.43-8.39(m, 1H), 8.11(s, 1H), 4.33(s, 3H), 3.20(q, J=7.5Hz, 2H), 1.24(t, J=7.5Hz, 3H).
1-1-051a δ9.58(d, J=5.8Hz, 1H), 8.76(d, J=1.0Hz, 1H), 8.35(d, J=1.0Hz, 1H), 7.50(dd, J=7.2 , 0.7Hz, 1H), 4.15(s, 3H), 4.06(q, J=7.5Hz, 2H), 1.47(t, J=7.5Hz, 3H).
1-1-051b δ8.93(d, J=6.1Hz, 1H), 8.73-8.70(m, 1H), 8.40-8.38(m, 1H), 7.40(d, J=7.8Hz, 1H), 4.29 (s, 3H), 3.09(q, J=7.4Hz, 2H), 1.22(t, J=7.4Hz, 3H).
1-1-052a δ9.45(s, 1H), 8.74(d, J=1.0Hz, 1H), 8.34(d, J=1.0Hz, 1H), 7.04(s, 1H), 4.13(s, 3H ), 4.05(s, 3H), 3.98(q, J=7.4Hz, 2H), 1.45(t, J=7.4Hz, 3H).
1-1-052b δ8.86(s, 1H), 8.70(d, J=1.4Hz, 1H), 8.37(d, J=1.4Hz, 1H), 6.96(s, 1H), 4.28(s, 3H ), 4.01(s, 3H), 3.05(q, J=7.5Hz, 2H), 1.20(t, J=7.5Hz, 3H).
1-1-053a δ9.81(d, J=2.4Hz, 1H), 8.91(d, J=2.4Hz, 1H), 8.78-8.75(m, 1H), 8.35(d, J=1.5Hz, 1H ), 4.26(s, 3H), 4.21(q, J=7.5Hz, 2H), 1.48(t, J=7.5Hz, 3H).
1-1-053b δ9.14(d, J=2.4Hz, 1H), 8.76(d, J=2.4Hz, 1H), 8.75-8.71(m, 1H), 8.39(d, J=1.5Hz, 1H ), 4.39(s, 3H), 3.19(q, J=7.5Hz, 2H), 1.24(t, J=7.5Hz, 3H).
1-1-056a δ9.49(d, J=1.5Hz, 1H), 9.14(d, J=1.5Hz, 1H), 8.78(s, 1H), 8.37(s, 1H), 4.22(s, 3H ), 4.18(q, J=7.5Hz, 2H), 1.48(t, J=7.5Hz, 3H).
1-1-058a δ9.14(s, 1H), 8.74(s, 1H), 8.33(s, 1H), 7.35(s, 1H), 4.15(s, 3H), 3.96(q, J=7.4Hz , 2H), 2.70(s, 3H), 1.43(t, J=7.4Hz, 3H).
1-1-058b δ8.75-8.65(m, 1H), 8.55-8.50(m, 1H), 8.40-8.35(m, 1H), 7.20-7.15(m, 1H), 4.30(s, 3H), 3.05(q, J=7.4Hz, 2H), 2.68(s, 3H), 1.19(t, J=7.4Hz, 3H).
1-1-059a δ9.28(d, J=1.6Hz, 1H), 8.75(d, J=1.6Hz, 1H), 8.34(d, J=1.6Hz, 1H), 7.65(d, J=1.6 Hz, 1H), 4.19(s, 3H), 4.08(q, J=7.4Hz, 2H), 1.46(t, J=7.4Hz, 3H).
1-1-059b δ8.75-8.70(m, 1H), 8.63(d, J=1.6Hz, 1H), 8.40-8.35(m, 1H), 7.46(d, J=1.6Hz, 1H), 4.34 (s, 3H), 3.13(q, J=7.4Hz, 2H), 1.22(t, J=7.4Hz, 3H).
1-1-060a δ9.18-9.14(m, 1H), 8.78-8.75(m, 1H), 8.37-8.34(m, 1H), 7.33-7.24(m, 1H), 4.19(s, 3H), 4.11(q, J=7.4Hz, 2H), 1.47(t, J=7.4Hz, 3H).
1-1-060b δ8.75-8.71(m, 1H), 8.50-8.46(m, 1H), 8.43-8.38(m, 1H), 7.15-7.05(m, 1H), 4.33(s, 3H), 3.14(q, J=7.4Hz, 2H), 1.22(t, J=7.4Hz, 3H).
1-1-061a δ9.50(d, J=1.4Hz, 1H), 8.76(d, J=1.4Hz, 1H), 8.35(d, J=1.4Hz, 1H), 8.25(d, J=1.4 Hz, 1H), 4.21(s, 3H), 4.08(q, J=7.4Hz, 2H), 1.46(t, J=7.4Hz, 3H).
1-1-061b δ8.86(d, J=1.4Hz, 1H), 8.72(d, J=1.0Hz, 1H), 8.39(d, J=1.0Hz, 1H), 8.05(d, J=1.4 Hz, 1H), 4.38(s, 3H), 3.14(q, J=7.4Hz, 2H), 1.22(t, J=7.4Hz, 3H).
1-1-062a δ9.45(d, J=1.4Hz, 1H), 8.78-8.75(m, 1H), 8.36-8.33(m, 1H), 7.85(d, J=1.4Hz, 1H), 4.19 (s, 3H), 4.07(q, J=7.5Hz, 2H), 1.47(t, J=7.5Hz, 3H).
1-1-062b δ8.82(d, J=1.4Hz, 1H), 8.72(d, J=1.0Hz, 1H), 8.39(d, J=1.0Hz, 1H), 7.66(d, J=1.4 Hz, 1H), 4.34(s, 3H), 3.13(q, J=7.4Hz, 2H), 1.23(t, J=7.4Hz, 3H).
1-1-063a δ9.30-9.25(m, 1H), 8.80-8.70(m, 1H), 8.40-8.30(m, 1H), 7.42(dd, J=8.9, 1.5Hz, 1H), 4.18( s, 3H), 4.10(q, J=7.4Hz, 2H), 1.47(t, J=7.4Hz, 3H).
1-1-063b δ8.75-8.70(m, 1H), 8.65-8.60(m, 1H), 8.40-8.35(m, 1H), 7.23(dd, J=9.2, 1.5Hz, 1H), 4.33( s, 3H), 3.14(q, J=7.4Hz, 2H), 1.22(t, J=7.4Hz, 3H).
1-1-064a δ9.08(d, J=1.2Hz, 1H), 8.74(d, J=1.2Hz, 1H), 8.33(d, J=1.2Hz, 1H), 7.03(d, J=1.2 Hz, 1H), 4.11(s, 3H), 4.10(s, 3H), 3.97(q, J=7.4Hz, 2H), 1.45(t, J=7.4Hz, 3H).
1-1-065a δ9.05(d, J=1.2Hz, 1H), 8.73(d, J=1.5Hz, 1H), 8.32(d, J=1.5Hz, 1H), 7.02(d, J=1.2 Hz, 1H), 4.31(q, J=7.0Hz, 2H), 4.09(s, 3H), 3.93(q, J=7.4Hz, 2H), 1.60(t, J=7.0Hz, 3H), 1.43( t, J=7.4Hz, 3H).
1-1-066a δ9.75-9.70(m, 1H), 8.80-8.70(m, 1H), 8.40-8.30(m, 1H), 8.10-8.00(m, 1H), 4.20(s, 3H), 4.17(q, J=7.4Hz, 2H), 1.48(t, J=7.4Hz, 3H).
1-1-067a δ9.74(d, J=1.5Hz, 1H), 8.78(d, J=1.8Hz, 1H), 8.36(d, J=1.8Hz, 1H), 8.14(d, J=1.5 Hz, 1H), 4.25(s, 3H), 4.19(q, J=7.5Hz, 2H), 1.48(t, J=7.5Hz, 3H).
1-1-067b δ9.08(d, J=1.7Hz, 1H), 8.76-8.73(m, 1H), 8.42-8.39(m, 1H), 7.96(d, J=1, 7Hz, 1H), 4.40(s, 3H), 3.20(q, J=7.4Hz, 2H), 1.25(t, J=7.4Hz, 3H).
1-1-068a δ8.92-8.89(m, 1H), 8.75-8.72(m, 1H), 8.34-8.32(m, 1H), 6.74-6.71(m, 1H), 4.10(s, 3H), 3.93(q, J=7.2Hz, 2H), 3.30(s, 6H), 1.43(t, J=7.2Hz, 3H).
1-1-069a δ9.60-9.50(m, 1H), 8.80-8.70(m, 1H), 8.40-8.30(m, 1H), 7.90-7.85(m, 1H), 4.21(s, 3H), 4.18(q, J=7.4Hz, 2H), 1.48(t, J=7.4Hz, 3H).
1-1-069b δ8.90-8.80(m, 1H), 8.75-8.70(m, 1H), 8.40-8.35(m, 1H), 7.70-7.65(m, 1H), 4.35(s, 3H), 3.19(q, J=7.4Hz, 2H), 1.24(t, J=7.4Hz, 3H).
1-1-070a δ9.55-9.50(m, 1H), 8.80-8.75(m, 1H), 8.40-8.30(m, 1H), 7.43(dd, J=9.0, 1.6Hz, 1H), 4.21( s, 3H), 4.16(q, J=7.4Hz, 2H), 1.48(t, J=7.4Hz, 3H).
1-1-070b δ8.90-8.85(m, 1H), 8.75-8.70(m, 1H), 8.45-8.35(m, 1H), 7.22(d, J=1.2Hz, 1H), 4.35(s, 3H), 3.19(q, J=7.4Hz, 2H), 1.24(t, J=7.4Hz, 3H).
1-1-071a δ9.68(s, 1H), 8.77(d, J=1.4Hz, 1H), 8.36(dJ=1.4Hz, 1H), 8.18(d, J=1.4Hz, 1H), 4.25( s, 3H), 4.15(q, J=7.3Hz, 2H), 1.48(t, J=7.3Hz, 3H).
1-1-071b δ9.03-8.99(m, 1H), 8.76-8.72(m, 1H), 8.43-8.39(m, 1H), 8.00(d, J=1.4Hz, 1H), 4.40(s, 3H), 3.19(q, J=7.4Hz, 2H), 1.24(t, J=7.4Hz, 3H).
1-1-072a δ9.33(s, 1H), 8.74(s, 1H), 8.34(s, 1H), 7.58(s, 1H), 4.13(s, 3H), 3.95(q, J=7.5Hz , 2H), 2.67(s, 3H), 1.43(t, J=7.5Hz, 3H).
1-1-072b δ8.74(s, 1H), 8.73(s, 1H), 8.45(s, 1H), 7.40(s, 1H), 4.31(s, 3H), 3.05(q, J=7.5Hz , 2H), 2.65(s, 3H), 1.19(t, J=7.5Hz, 3H).
1-1-072c δ9.57(s, 1H), 8.71(d, J=1.5Hz, 1H), 8.30(d, J--=1.5Hz, 1H), 7.46-7.42(m, 1H), 4.44 (s, 3H), 3.75-3.40(m, 2H), 2.65(s, 3H), 1.54(t, J=7.5Hz, 3H).
1-1-073a δ9.00-8.90(m, 1H), 8.75-8.70(m, 1H), 8.35-8.30(m, 1H), 7.51(d, J=1.2Hz, 1H), 4.15(s, 3H), 4.00(q, J=7.4Hz, 2H), 2.47(d, J=0.8Hz, 3H), 1.44(t, J=7.4Hz, 3H).
1-1-073b δ8.75-8.65(m, 1H), 8.40-8.30(m, 2H), 7.33(d, J=1.2Hz, 1H), 4.32(s, 3H), 3.07(q, J= 7.4Hz, 2H), 2.45(d, J=0.8Hz, 3H), 1.19(t, J=7.4Hz, 3H).
1-1-074a δ9.34(s, 1H), 8.77-8.75(m, 1H), 8.36-8.34(m, 1H), 7.52(dd, J=8.7, 1.2Hz, 1H), 4.18(s, 3H), 4.09(q, J=7.5Hz, 2H), 1.47(t, J=7.5Hz, 3H).
1-1-074b δ8.74-8.71(m, 2H), 8.42-8.38(m, 1H), 7.36-7.30(m, 1H), 4.33(s, 3H), 3.14(q, J=7.4Hz, 2H), 1.23(t, J=7.4Hz, 3H).
1-1-075a δ8.84(d, J=1.5Hz, 1H), 8.75-8.73(m, 1H), 8.34-8.32(m, 1H), 7.12(d, J=1.5Hz, 1H), 4.16 (s, 3H), 4.02(q, J=7.5Hz, 2H), 2.65(s, 3H), 2.59(s, 3H), 1.44(t, J=7.5Hz, 3H).
1-1-076a δ9.70-9.60(m, 1H), 8.80-8.75(m, 1H), 8.40-8.30(m, 1H), 8.00-7.95(m, 1H), 4.22(s, 3H), 4.14(q, J=7.4Hz, 2H), 1.47(t, J=7.4Hz, 3H).
1-1-077a δ9.47(d, J=7.2Hz, 1H), 8.76(d, J--=1.2Hz, 1H), 8.35(d, J--=1.2Hz, 1H), 7.90(d , J=7.2Hz, 1H), 7.30-7.20(m, 1H), 4.21(s, 3H), 4.14(q, J=7.5Hz, 2H), 1.46(t, J=7.5Hz, 3H).
1-1-077b δ8.83(d, J=7.5Hz, 1H), 8.71(s, 1H), 8.39(s, 1H), 7.72(d, J=6.6Hz, 1H), 7.10(t, J =6.6Hz, 1H), 4.36(s, 3H), 3.15(q, J=7.5Hz, 2H), 1.22(t, J=7.5Hz, 3H).
1-1-078a δ9.41(s, 1H), 8.78-8.76(m, 1H), 8.37-8.34(m, 1H), 4.21(s, 3H), 4.12(q, J=7.4Hz, 2H) , 1.47(t, J=7.4Hz, 3H).
1-1-078b δ8.74(d, J=0.7Hz, 1H), 8.74-8.72(m, 1H), 8.41-8.38(m, 1H), 4.36(s, 3H), 3.16(q, J= 7.5Hz, 2H), 1.23(t, J=7.5Hz, 3H).
1-1-079a δ9.41(s, 1H), 8.75(s, 1H), 8.34(s, 1H), 7.94-7.80(m, 2H), 7.68-7.60(m, 2H), 7.58-7.42( m, 3H), 4.15(s, 3H), 3.99(q, J=7.5Hz, 2H), 1.46(t, J=7.5Hz, 3H).
1-1-080a δ9.41(s, 1H), 8.75(d, J=1.8Hz, 1H), 8.35(d, J=1.8Hz, 1H), 7.95-7.75(m, 2H), 7.70-7.25 (m, 4H), 4.15(s, 3H), 4.00(q, J=7.5Hz, 2H), 1.47(t, J=7.5Hz, 3H).
1-1-081a δ9.43(s, 1H), 8.75(d, J=1.8Hz, 1H), 8.35(d, J=1.8Hz, 1H), 7.95-7.75(m, 2H), 7.60-7.15 (m, 4H), 4.16(s, 3H), 4.02(q, J=7.5Hz, 2H), 1.47(t, J=7.5Hz, 3H).
1-1-082a δ9.40-9.36(m, 1H), 8.75(d, J=1.8Hz, 1H), 8.35(d, J=1.8Hz, 1H), 7.95-7.75(m, 2H), 7.70 -7.55(m, 2H), 7.25-7.20(m, 2H), 4.16(s, 3H), 4.02(q, J=7.5Hz, 2H), 1.46(t, J=7.5Hz, 3H).
1-1-083a δ9.20(s, 1H), 8.75(s, 1H), 8.34(s, 1H), 8.01(s, 1H), 7.90-7.80(m, 2H), 7.70-7.30(m, 3H), 4.16(s, 3H), 3.98(q, J=7.5Hz, 2H), 1.43(t, J=7.5Hz, 3H).
1-1-084a δ9.47(s, 1H), 8.76(s, 1H), 8.36(s, 1H), 7.95-7.30(m, 6H), 4.17(s, 3H), 4.05(q, J= 7.5Hz, 2H), 1.47(t, J=7.5Hz, 3H).
1-1-085a δ9.49(s, 1H), 8.76(s, 1H), 8.36(s, 1H), 7.94(d, J=9.6Hz, 1H), 7.85-7.35(m, 5H), 4.17 (s, 3H), 4.05(q, J=7.5Hz, 2H), 1.47(t, J=7.5Hz, 3H).
1-1-086a δ9.47(s, 1H), 8.92(s, 1H), 8.80-8.70(m, 2H), 8.36(s, 1H), 7.97(s, 1H), 7.94(s, 1H) , 7.80(dd, J=9.6, 1.8Hz, 1H), 7.55-7.43(m, 1H), 4.17(s, 3H), 4.05(q, J=7.5Hz, 2H), 1.48(t, J=7.5 Hz, 3H).
1-1-087a δ9.56(s, 1H), 8.82-8.74(m, 3H), 8.36(s, 1H), 7.96(d, J=9.6Hz, 1H), 7.84(d, J=9.6Hz , 1H), 7.65-7.53(m, 2H) 4.18(s, 3H), 4.08(q, J=7.5Hz, 2H), 1.48(t, J=7.5Hz, 3H).
1-1-088a δ9.45(s, 1H), 8.75(s, 1H), 8.34(s, 1H), 7.85-7.80(m, 2H), 7.65-7.40(m, 3H), 4.15(s, 3H), 4.01(q, J=7.5Hz, 2H), 1.46(t, J=7.5Hz, 3H).
1-1-089a δ9.34(d, J=0.9Hz, 1H), 8.75(s, 1H), 8.34(s, 1H), 7.74(d, J=9.6Hz, 1H), 7.56(dd, J =9.6, 1.8Hz, 1H), 4.14(s, 3H), 4.01(q, J=7.5Hz, 2H), 1.46(t, J=7.5Hz, 3H), 0.30(s, 9H).
1-1-090a δ9.22(s, 1H), 8.75-8.72(m, 1H), 8.34-8.31(m, 1H), 7.70(d, J=9.3Hz, 1H), 7.49(dd, J= 9.3, 1.8Hz, 1H), 4.12(s, 3H), 3.97(q, J=7.5Hz, 2H), 1.44(t, J=7.5Hz, 3H), 1.00-0.80(m, 5H).
1-1-091a δ9.24(s, 1H), 8.74(s, 1H), 8.34(s, 1H), 7.77(d, J=1.5Hz, 2H), 5.56(s, 1H), 5.32(s , 1H), 4.13(s, 3H), 3.99(q, J=7.5Hz, 2H), 2.24(s, 3H) 1.45(t, J=7.5Hz, 3H).
1-1-092a δ9.65(s, 1H), 8.45(d, J=2.0Hz, 1H), 8.10(d, J=2.0Hz, 1H), 7.94(d, J=9.2Hz, 1H), 7.71(d, J=9.2Hz, 1H), 4.13(s, 3H), 4.10(q, J=7.3Hz, 2H), 1.47(t, J=7.3Hz, 3H).
1-1-092b δ9.03-8.99(m, 1H), 8.41(d, J=2.4Hz, 1H), 8.14(d, J=2.4Hz, 1H), 7.82(d, J=9.5Hz, 1H ), 7.52(d, J=9.5Hz, 1H), 4.26(s, 3H), 3.11(q, J=7.4Hz, 2H), 1.21(t, J=7.4Hz, 3H).
1-1-093a δ9.34-9.32(m, 1H), 8.71-8.69(m, 1H), 8.33-8.31(m, 1H), 7.79(dd, J=9.5, 1.0Hz, 1H), 7.55( dd, J=9.5, 1.9Hz, 1H), 4.16(s, 3H), 4.06(q, J=7.4Hz, 2H), 1.47(t, J=7.4Hz, 3H).
1-1-093b δ8.69(dd, J=2.0, 1.0Hz, 1H), 8.66(d, J=1.7Hz, 1H), 8.37(d, J=1.7Hz, 1H), 7.67(dd, J =9.5, 1.0Hz, 1H), 7.36(dd, J=9.5, 2.0Hz, 1H), 4.32(s, 3H), 3.12(q, J=7.5Hz, 2H), 1.23(t, J=7.5Hz , 3H).
1-1-094a δ9.50(dd, J=1.5, 0.9Hz, 1H), 8.70(d, J=2.0Hz, 1H), 8.32(d, J=2.0Hz, 1H), 7.76(dd, J =9.4, 1.5Hz, 1H), 7.61(dd, J=9.4, 0.9Hz, 1H), 4.15(s, 3H), 4.05(q, J=7.4Hz, 2H), 1.47(t, J=7.4Hz , 3H).
1-1-094b δ8.91-8.89(m, 1H), 8.67-8.65(m, 1H), 8.37-8.35(m, 1H), 7.56(dd, J=9.4, 1.5Hz, 1H), 7.50( dd, J=9.4, 0.9Hz, 1H), 4.31(s, 3H), 3.11(q, J=7.3Hz, 2H), 1.23(t, J=7.3Hz, 3H).
1-1-094c δ9.74-9.72(m, 1H), 8.68-8.66(m, 1H), 8.29-8.27(m, 1H), 7.62(dd, J=9.4, 1.7Hz, 1H), 7.55( dd, J=9.4, 0.9Hz, 1H), 4.43(s, 3H), 3.75-3.64(m, 1H), 3.63-3.49(m, 1H), 1.57(t, J=7.5Hz, 3H).
1-1-095a δ9.05(d, J=1.2Hz, 1H), 8.74(d, J=0.9Hz, 1H), 8.33(d, J=1.5Hz, 1H), 7.73(dd, J=9.3 , 0.6Hz, 1H), 7.50(dd, J=9.3, 1.5Hz, 1H), 4.13(s, 3H), 4.00(q, J=7.2Hz, 2H), 2.59(s, 3H), 1.45(t , J=7.2Hz, 3H).
1-1-096a δ9.57(s, 1H), 8.77(s, 1H), 8.36(s, 1H), 8.00(d, J=9.6Hz, 1H), 7.81(dd, J=9.6, 1.8Hz , 1H), 4.18(s, 3H), 4.18-4.00(m, 2H), 2.91(s, 3H), 1.47(t, J=7.2Hz, 3H).
1-1-097a δ9.93(s, 1H), 8.77(s, 1H), 8.37(s, 1H), 8.02-7.90(m, 2H), 4.19(s, 3H), 4.12(q, J= 7.5Hz, 2H), 3.23(s, 3H), 1.49(t, J=7.5Hz, 3H).
1-1-098a δ9.48-9.46(m, 1H), 8.76(d, J=1.4Hz, 1H), 8.35(d, J=1.4Hz, 1H), 7.81(dd, J=9.4, 0.9Hz , 1H), 7.67(dd, J=9.4, 1.7Hz, 1H), 4.15(s, 3H), 4.04(q, J=7.4Hz, 2H), 3.47(q, J=18.7Hz, 2H), 1.46 (t, J=7.4Hz, 3H).
1-1-099a δ9.07(dd, J=1.7, 0.9Hz, 1H), 8.69(d, J=1.7Hz, 1H), 8.31(d, J=1.7Hz, 1H), 7.74(dd, J =9.4, 0.9Hz, 1H), 7.51(dd, J=9.4, 1.7Hz, 1H), 4.15(s, 3H), 4.02(q, J=7.3Hz, 2H), 2.60(s, 3H), 1.46 (t, J=7.3Hz, 3H).
1-1-100a δ9.47(s, 1H), 8.73(d, J=1.5Hz, 1H), 8.33(d, J=1.5Hz, 1H), 7.74(d, J=9.6Hz, 1H), 7.58(d, J=9.6Hz, 1H), 6.60(brs, 1H), 4.11(s, 3H), 3.93(q, J=7.5Hz, 2H), 1.56(s, 9H)1.45(t, J= 7.5Hz, 3H).
1-1-101a δ9.47(d, J=2.1Hz, 1H), 8.80-8.77(m, 1H), 8.75(d, J=1.5Hz, 1H), 8.39-8.35(m, 1H), 7.95 (dd, J=7.8, 2.4Hz, 1H), 4.21(s, 3H), 4.17(q, J=7.5Hz, 2H), 1.47(t, J=7.5Hz, 3H).
1-1-101b δ8.82-8.72(m, 2H), 8.70-8.66(m, 1H), 8.40(d, J=2.1Hz, 1H), 7.85(dd, J=7.5, 2.1Hz, 1H) , 4.35(s, 3H), 3.21(q, J=7.5Hz, 2H), 1.22(t, J=7.5Hz, 3H).
1-1-102a δ9.42(d, J=7.5Hz, 1H), 8.50(dd, J=4.8, 1.4Hz, 1H), 8.16-8.13(m, 1H), 8.10(dd, J=7.5, 1.4Hz, 1H), 7.33-7.28(m, 2H), 4.15(s, 3H), 4.14(q, J=7.3Hz, 2H), 1.45(t, J=7.3Hz, 3H).
1-1-102b δ8.76(d, J=7.2Hz, 1H), 8.47(dd, J=4.8, 1.4Hz, 1H), 8.16(dd, J=8.2, 1.4Hz, 1H), 8.04(s , 1H), 7.29(dd, J=8.2, 4.8Hz, 1H), 7.19(dd, J=7.2, 1.7Hz, 1H), 4.28(s, 3H), 3.11(q, J=7.4Hz, 2H) , 1.19(t, J=7.4Hz, 3H).
1-1-103a δ9.42(d=7.5Hz, 1H), 8.72(d, J=1.7Hz, 1H), 8.33(d, J=1.7Hz, 1H), 8.17-8.15(m, 1H), 7.33(dd, J=7.5Hz, 1.7Hz, 1H), 4.19(s, 3H), 4.13(q, J=7.5Hz, 2H), 1.47(t, J=7.5Hz, 3H).
1-1-103b δ8.78(d, J=7.2Hz, 1H), 8.68(d, J=1.7Hz, 1H), 8.38(d, J=1.7Hz, 1H), 8.05(s, 1H), 7.21(dd, J=7.2, 1.7Hz, 1H), 4.34(s, 3H), 3.16(q, J=7.4Hz, 2H), 1.23(t, J=7.4Hz, 3H).
1-1-104a δ 10.35(s, 1H), 8.77(s, 1H), 8.39-8.35(m, 1H), 8.22(s, 1H), 8.06-8.02(m, 1H), 7.96-7.90( m, 2H), 7.67-7.62(m, 1H), 7.62-7.54(m, 2H), 4.16(s, 3H), 4.06(q, J=7.7Hz, 2H), 1.54(t, J=7.7Hz , 3H).
1-1-105a δ9.92-9.89(m, 1H), 8.81-8.78(m, 1H), 8.38(d, J=1.5Hz, 1H), 8.12(d, J=1.5Hz, 1H), 4.29 (s, 3H), 4.12(q, J=7.1Hz, 2H), 1.26(t, J=7.1Hz, 3H).
1-1-105b δ9.22-9.19(m, 1H), 8.76(d, J=1.4Hz, 1H), 8.42(d, J=1.4Hz, 1H), 7.96(d, J=1.4Hz, 1H ), 4.42(s, 3H), 3.26(q, J=7.3Hz, 2H), 1.26(t, J=7.3Hz, 3H).
1-1-105c δ 10.22-10.19(m, 1H), 8.78-8.76(m, 1H), 8.34(d, J=1.7Hz, 1H), 8.00(d, J=1.7Hz, 1H), 4.51 (s, 3H), 3.81-3.57(m, 2H), 1.58(t, J=7.7Hz, 3H).
1-1-106a δ9.36(dd, J=7.5, 0.7Hz, 1H), 8.76(d, J=1.0Hz, 1H), 8.36(d, J=1.7Hz, 1H), 8.00-7.97(m , 1H), 7.32-7.27(m, 1H), 6.79(t, J=55.5Hz, 1H), 4.17(s, 3H), 4.07(q, J=7.5Hz, 2H), 1.46(t, J= 7.5Hz, 3H).
1-1-106b δ8.75(dd, J=7.2, 0.7Hz, 1H), 8.72(dd, J=2.0, 0.7Hz, 1H), 8.40(d, J=2.0Hz, 1H), 7.88-7.85 (m, 1H), 7.18(dd, J=7.2, 2.0Hz, 1H), 6.76(t, J=55.7Hz, 1H), 4.32(s, 3H), 3.12(q, J=7.4Hz, 2H) , 1.21(t, J=7.4Hz, 3H).
1-1-106c δ9.56(d, J=7.4Hz, 1H), 8.72(d, J=1.8Hz, 1H), 8.32(d, J=1.8Hz, 1H), 7.93-7.90(m, 1H ), 7.11(dd, J=7.4, 1.5Hz, 1H), 6.75(t, J=55.7Hz, 1H), 4.43(s, 3H), 3.80-3.64(m, 1H), 3.63-3.47(m, 1H), 1.55(t, J=7.5Hz, 3H).
1-1-107a δ8.73(d, J=1.4Hz, 1H), 8.65-8.63(m, 1H), 8.32(d, J=2.0Hz, 1H), 7.64(d, J=9.5Hz, 1H ), 7.13(dd, J=9.5, 2.0Hz, 1H), 4.11(s, 3H), 3.92(q, J=7.4Hz, 2H), 3.83(brs, 2H), 1.43(t, J=7.4Hz , 3H).
1-1-108a δ9.72(s, 1H), 8.76(d, J=2.0Hz, 1H), 8.35(d, J=2.0Hz, 1H), 7.80(d, J=9.5Hz, 1H), 7.71(d, J=9.5Hz, 1H), 4.14(s, 3H), 3.99(q, J=7.5Hz, 2H), 1.45(t, J=7.5Hz, 3H) (NH proton peak is observed could not).
1-1-109a δ9.49(dd, J=6.5, 0.7Hz, 1H), 8.80-8.70(m, 1H), 8.35-8.30(m, 1H), 7.53(dd, J=7.7, 0.7Hz, 1H), 4.14(s, 3H), 4.07(q, J=7.4Hz, 2H), 1.46(t, J=7.4Hz, 3H).
1-1-109b δ8.83(d, J=6.5Hz, 1H), 8.75-8.65(m, 1H), 8.40-8.35(m, 1H), 7.44(d, J=8.5Hz, 1H), 4.28 (s, 3H), 3.09(q, J=7.5Hz, 2H), 1.21(t, J=7.5Hz, 3H).
1-1-110a δ9.52(s, 1H), 8.75(d, J=2.0Hz, 1H), 8.34(d, J=2.0Hz, 1H), 7.96(s, 1H), 4.15(s, 3H ), 4.07(q, J=7.4Hz, 2H), 1.46(t, J=7.4Hz, 3H).
1-1-110c δ9.78(d, J=0.7Hz, 1H), 8.75-8.70(m, 1H), 8.35-8.25(m, 1H), 7.90(d, J=0.7Hz, 1H), 4.40 (s, 3H), 3.75-3.45(m, 2H), 1.55(t, J=7.3Hz, 3H).
1-1-111a δ9.60(d, J=0.7Hz, 1H), 8.80-8.75(m, 1H), 8.40-8.30(m, 1H), 8.23(d, J=0.7Hz, 1H), 4.18 (s, 3H), 4.17(q, J=7.5Hz, 2H), 1.48(t, J=7.5Hz, 3H).
1-1-111b δ8.93(d, J=0.7Hz, 1H), 8.75-8.70(m, 1H), 8.40-8.35(m, 1H), 8.17(d, J=0.7Hz, 1H), 4.32 (s, 3H), 3.20(q, J=7.4Hz, 2H), 1.23(t, J=7.4Hz, 3H).
1-1-112a δ9.37(d, J=1.5Hz, 1H), 8.80-8.70(m, 1H), 8.40-8.30(m, 1H), 7.75(d, J=1.5Hz, 1H), 4.18 (s, 3H), 4.07(q, J=7.4Hz, 2H), 1.46(t, J=7.4Hz, 3H).
1-1-112b δ8.75-8.70(m, 2H), 8.45-8.30(m, 1H), 7.56(d, J=1.5Hz, 1H), 4.34(s, 3H), 3.13(q, J= 7.5Hz, 2H), 1.22(t, J=7.5Hz, 3H).
1-1-113a δ9.24(dd, J=4.4, 2.0Hz, 1H), 8.80-8.70(m, 1H), 8.35-8.30(m, 1H), 7.61(dd, J=7.7, 2.0Hz, 1H), 4.19(s, 3H), 4.08(q, J=7.4Hz, 2H), 1.45(t, J=7.4Hz, 3H).
1-1-113b δ8.75-8.65(m, 1H), 8.55(dd, J=3.7, 2.4Hz, 1H), 8.40-8.35(m, 1H), 7.43(dd, J=7.8, 2.4Hz, 1H), 4.34(s, 3H), 3.12(q, J=7.4Hz, 2H), 1.21(t, J=7.4Hz, 3H).
1-1-114a δ9.39(s, 1H), 8.75(d, J=1.8Hz, 1H), 8.43(s, 1H), 8.34(d, J=1.8Hz, 1H) 4.14(s, 3H) , 4.07(q, J=7.5Hz, 2H), 1.45(t, J=7.5Hz, 3H).
1-1-114b δ8.76(d, J=0.7Hz, 1H), 8.73-8.71(m, 1H), 8.40-8.38(m, 1H), 8.31(d, J=0.7Hz, 1H), 4.29 (s, 3H), 9, 3.12(d, J=7.4Hz, 2H), 1.21(t, J=7.4Hz, 3H).
1-1-115a δ9.42(d, J=0.6Hz, 1H), 8.75(dd, J=1.8, 0.6Hz, 1H), 8.34(dd, J=1.8, 0.6Hz, 1H), 8.17(d , J=0.6Hz, 1H), 4.15(s, 3H), 4.08(q, J=7.5Hz, 2H), 1.46(t, J=7.5Hz, 3H).
1-1-115b δ8.77(d, J=0.7Hz, 1H), 8.73-8.71(m, 1H), 8.40-8.38(m, 1H), 8.06(d, J=0.7Hz, 1H), 4.30 (s, 3H), 3.12(q, J=7.4Hz, 2H), 1.22(t, J=7.4Hz, 3H).
1-1-116a δ 9.24 (s, 1H), 8.75 (d, J=2.0Hz, 1H), 8.34 (d, J=2.0Hz, 1H), 7.40 (s, 1H), 4.15 (s, 3H ), 4.03 (q, J=7.4Hz, 2H), 2.62 (s, 3H), 1.46 (t, J=7.4Hz, 3H).
1-1-117a δ9.42 (s, 1H), 8.80-8.75 (m, 1H), 8.44 (s, 1H), 8.39-8.32 (m, 1H), 4.21 (s, 3H), 4.13 (q, J=7.3Hz, 2H), 3.00 (s, 3H), 1.49 (t, J=7.3 Hz, 3H).
1-1-118a δ9.33(d, J=1.7Hz, 1H), 8.80-8.70(m,1H), 8.35-8.30(m,1H), 7.83(d, J=1.7Hz,1H), 4.19 (s,3H), 4.07(q, J=7.4Hz, 2H), 1.45(t, J=7.4Hz, 3H).
1-1-118b δ8.75-8.70(m, 1H), 8.67(d, J=1.7Hz, 1H), 8.40-8.35(m, 1H), 7.64(d, J=1.7Hz, 1H), 4.35 (s, 3H), 3.13(q, J=7.4Hz, 2H), 1.21(t, J=7.4Hz, 3H).
1-1-118c δ9.57(d, J=1.7Hz, 1H), 8.75-8.70(m, 1H), 8.35-8.25(m, 1H), 7.70(d, J=1.7Hz, 1H), 4.47 (s, 3H), 3.75-3.50(m, 2H), 1.55(t, J=7.5Hz, 3H).
1-1-119b δ8.75-8.65(m, 1H), 8.63(s, 1H), 8.40-8.30(m, 1H), 4.33(s, 3H), 3.10(q, J=7.4Hz, 2H) , 2.63(s, 3H), 1.20(t, J=7.4Hz, 3H).
1-1-119c δ9.52(s, 1H), 8.75-8.70(m, 1H), 8.35-8.25(m, 1H), 4.46(s, 3H), 3.75-3.45(m, 2H), 2.63( s, 3H), 1.54(t, J=7.3Hz, 3H).
1-1-120c δ9.37(d, J=4.8Hz, 1H), 9.30-9.25(m, 1H), 8.75-8.70(m, 1H), 8.35-8.30(m, 1H), 8.04(d, J=4.8Hz, 1H), 4.46(s, 3H), 3.80-3.50(m, 2H), 1.55(t, J=7.3Hz, 3H).
1-1-121a δ9.22(d, J=3.7Hz, 1H), 8.80-8.70(m, 1H), 8.35-8.30(m, 2H), 4.15(s, 3H), 4.07(q, J= 7.4Hz, 2H), 1.44(t, J=7.4Hz, 3H).
1-1-122a δ9.42 (d, J=7.5Hz, 1H), 8.79 (d, J=2.0Hz, 1H), 8.60 (d, J=2.0Hz, 1H), 8.19-8.15 (m, 1H ), 7.34 (dd, J=7.5, 1.7Hz, 1H), 4.21 (s, 3H), 4.12 (q, J=7.5Hz, 2H), 1.48 (t, J=7.5Hz, 3H).
1-1-123a δ9.42 (d, J=7.5Hz, 1H), 9.08 (d, J=2.0Hz, 1H), 8.72 (d, J=2.0Hz, 1H), 8.19-8.16 (m, 1H ), 7.35 (dd, J=7.5, 1.7Hz, 1H), 4.24 (s, 3H), 4.10 (q, J=7.4Hz, 2H), 1.49 (t, J=7.4Hz, 3H).
1-1-131a δ9.30-9.20(m, 1H), 8.76(d, J=2.0Hz, 1H), 8.57(d, J=2.0Hz, 1H), 7.90-7.75(m, 1H), 7.55 -7.45(m, 1H), 4.18(s, 3H), 4.05(q, J=7.5Hz, 2H), 1.46(t, J=7.5Hz, 3H).
1-1-165a δ9.65-9.58 (m, 1H), 8.79 (d, J=1.7Hz, 1H), 8.61 (d, J=1.7Hz, 1H), 7.80 (d, J=1.7Hz, 1H ), 4.25 (s, 3H), 4.12 (q, J=7.5Hz, 2H), 1.48 (t, J=7.5Hz, 3H).
1-1-168a δ9.69(d, J=1.2Hz, 1H), 8.79(d, J=2.0Hz, 1H), 8.60(d, J=2.0Hz, 1H), 7.75(d, J=1.2 Hz, 1H), 4.26(s, 3H), 4.18(q, J=7.4Hz, 2H), 1.49(t, J=7.4Hz, 3H).
1-1-173a δ9.35(d, J=1.6Hz, 1H), 9.17(dd, J=4.9, 1.6Hz, 1H), 8.77(d, J=2.0Hz, 1H), 8.36(d, J =2.0Hz, 1H), 8.23(d, J=4.9Hz, 1H), 4.22(s, 3H), 4.15(q, J=7.5Hz, 2H), 1.46(t, J=7.5Hz, 3H).
1-1-185a δ8.95(dd, J=7.2, 0.9Hz, 1H), 8.78-8.75(m, 1H), 8.35 (dd, J=2.1, 0.9Hz, 1H), 7.65(dd, J= 7.8, 0.9Hz, 1H), 7.15(dd, J=7.8, 7.2Hz, 1H), 4.12(s, 3H), 3.95(q, J=7.2Hz, 2H), 3.19(s, 3H), 1.44( t, J=7.2Hz, 3H) (NH proton peak could not be observed).
1-1-189a δ8.91(d, J=7.8Hz, 1H), 8.72(s, 1H), 8.31(s, 1H), 6.64(d, J=7.8Hz, 1H), 4.85-4.75(brs , 2H), 4.15(s, 3H), 3.92(q, J=7.4Hz, 2H), 1.41(t, J=7.4Hz, 3H).
1-1-195a δ9.24(d, J=7.8Hz, 1H), 8.75(d, J=1.5Hz, 1H), 8.34(d, J=2.1Hz, 1H), 8.29(d, J=2.4 Hz, 1H), 7.28(dd, J=7.8, 2.4Hz, 1H), 4.16(s, 3H), 4.05(q, J=7.5Hz, 2H), 1.44(t, J=7.5Hz, 3H) ( The proton peak of NH could not be observed.)
1-1-198a δ8.90(d, J=7.8Hz, 1H), 8.72-8.70(m, 1H), 8.32(d, J=2.1Hz, 1H), 6.80(d, J=2.1Hz, 1H ), 6.58(dd, J=7.8, 2.4Hz, 1H), 4.35(brs, 2H), 4.10(s, 3H), 3.88(q, J=7.5Hz, 2H), 1.42(t, J=7.5Hz , 3H).
1-2-004a δ9.46(d, J=7.5Hz, 1H), 8.80(d, J=1.4Hz, 1H), 8.47(d, J=2.0Hz, 1H), 8.20(s, 1H), 7.35(dd, J=7.5, 2.0Hz, 1H), 4.00(q, J=7.4Hz, 2H), 1.48(t, J=7.4Hz, 3H).
1-2-004b δ8.78-8.72(m, 2H), 8.43(d, J=2.0Hz, 1H), 8.09(s, 1H), 7.23(dd, J=7.3, 2.0Hz, 1H), 3.10 (q, J=7.4Hz, 2H), 1.27(t, J=7.4Hz, 3H).
1-2-004c δ9.54(d, J=7.5Hz, 1H), 8.75(d, J=1.4Hz, 1H), 8.40(d, J=1.4Hz, 1H), 8.13(s, 1H), 7.20(dd, J=7.5, 1.4Hz, 1H), 3.66-3.39(m, 2H), 1.50(t, J=7.5Hz, 3H).
1-2-005a δ9.50(d, J=7.4Hz, 1H), 8.25-8.20(m, 1H), 8.20-8.10(m, 1H), 7.80-7.70(m, 2H), 7.31(dd, J=7.4, 1.8Hz, 1H), 4.08(q, J=7.4Hz, 2H), 1.45(t, J=7.4Hz, 3H).
1-2-006a δ9.49(d, J=7.4Hz, 1H), 8.65-8.60(m, 1H), 8.20-8.10(m, 2H), 7.98(d, J=8.6Hz, 1H), 7.34 (dd, J=7.4, 1.8Hz, 1H), 4.06(q, J=7.4Hz, 2H), 1.47(t, J=7.4Hz, 3H).
1-3-002a δ9.41(d, J=7.5Hz, 1H), 8.44(s, 1H), 8.10-8.07(m, 1H), 7.91(s, 1H), 7.27-7.23(m, 1H) , 3.84(q, J=7, 4Hz, 2H), 2.99(s, 3H), 1.36(t, J=7.4Hz, 3H).
1-3-003a δ9.41(d, J=7.5Hz, 1H), 8.44(s, 1H), 8.09-8.07(m, 1H), 7.95(s, 1H), 7.27-7.22(m, 1H) , 3.87(q, J=7.4Hz, 2H), 2.98(s, 3H), 1.37(t, J=7.4Hz, 3H).
1-3-004a δ9.39(d, J=7.5Hz, 1H), 9.20(s, 1H), 8.63(s, 1H), 8.12-8.08(m, 1H), 8.05(s, 1H), 7.25 (dd, J=7.5, 1.8Hz, 1H), 3.75(q, J=7.4Hz, 2H), 1.35(t, J=7.5Hz, 3H).
1-3-005a δ 9.63(s, 1H), 9.19(s, 1H), 8.65(s, 1H), 8.01(s, 1H), 7.93(d, J=9.3Hz, 1H), 7.66(dd , J=9.3, 1.5Hz, 1H), 3.69(q, J=7.5Hz, 2H), 1.34(t, J=7.5Hz, 3H).
1-3-006a δ 9.66(s, 1H), 8.46(s, 1H), 7.94-7.86(m, 2H), 7.65(dd, J=9.3, 1.5Hz, 1H), 3.82(q, J= 7.5Hz, 2H), 2.98(s, 3H), 1.37(t, J=7.5Hz, 3H).
1-3-009a δ9.61(s, 1H), 9.23(s, 1H), 7.96(d, J=9.6Hz, 1H), 7.94(s, 1H), 7.68(d, J=9.6Hz, 1H ), 4.00(q, J=7.5Hz, 2H), 1.45(t, J=7.5Hz, 3H).
1-3-011a δ9.65(s, 1H), 8.98(s, 1H), 7.96(d, J=1.5Hz, 1H), 7.88(d, J=9.3Hz, 1H), 7.64(dd, J =9.3, 1.5Hz, 1H), 4.09(q, J=7.5Hz, 2H), 2.94(s, 3H), 1.44(t, J=7.5Hz, 3H).
1-3-012a δ9.46-9.44(m, 1H), 9.24(d, J=0.7Hz, 1H), 8.67(s, 1H), 7.99(s, 1H), 7.71(dd, J=9.5, 1.7Hz, 1H), 7.61(dd, J=9.5, 0.7Hz, 1H), 3.63(q, J=7.3Hz, 2H), 1.33(t, J=7.3Hz, 3H).
1-3-013a δ9.40-9.30(m, 1H), 9.25-9.15(m, 1H), 8.20-8.15(m, 1H), 7.95-7.90(m, 1H), 7.30-7.20(m, 1H ), 3.99(q, J=7.5Hz, 2H), 1.43(t, J=7.5Hz, 3H).
1-3-014a δ9.41(d, J=7.5Hz, 1H), 8.99(s, 1H), 8.09(s, 1H), 7.97(d, J=1.5Hz, 1H), 7.30-7.20(m , 1H), 4.10(q, J=7.5Hz, 2H), 2.94(s, 3H), 1.43(t, J=7.5Hz, 3H).
1-4-002a δ9.65(s, 1H), 8.94(s, 1H), 8.57(d, J=2.1Hz, 1H), 8.31(s, 1H), 7.91(d, J=9.3Hz, 1H ), 7.64(dd, J=9.3, 2.1Hz, 1H), 3.76(q, J=7.5Hz, 2H), 1.36(t, J=7.5Hz, 3H).
1-4-003a δ9.48(dd, J=1.7, 1.0Hz, 1H), 8.94(s, 1H), 8.56(d, J=2.0Hz, 1H), 8.31-8.29(m, 1H), 7.69 (dd, J=9.4, 1.7Hz, 1H), 7.60(dd, J=9.4, 1.0Hz, 1H), 3.69(q, J=7.4Hz, 2H), 1.34(t, J=7.4Hz, 3H) .
1-4-003b δ9.05-9.00(m, 1H), 8.80-8.70(m, 1H), 8.55-8.50(m, 1H), 8.30-8.25(m, 1H), 7.55-7.45(m, 2H ), 2.86(q, J=7.4Hz, 2H), 1.20(t, J=7.4Hz, 3H).
1-5-001a δ9.39(d, J=7.4Hz, 1H), 8.54(s, 1H), 8.30(d, J=7.4Hz, 1H), 8.07(s, 1H), 8.01(s, 1H ), 7.21(dd, J=7.4, 1.7Hz, 1H), 7.04(dd, J=7.4, 1.7Hz, 1H), 3.75(q, J=7.5Hz, 2H), 1.31(t, J=7.5Hz , 3H).
1-5-003a δ9.38(d, J=7.5Hz, 1H), 8.59(s, 2H), 8.10(s, 1H), 7.82(d, J=9.5Hz, 1H), 7.40(dd, J =9.5, 2.0Hz, 1H), 7.22(dd, J=7.5, 2.0Hz, 1H), 3.66(q, J=7.4Hz, 2H), 1.31(t, J=7.4Hz, 3H).
1-5-004a δ9.64(s, 1H), 8.61(s, 1H), 8.59(s, 1H), 7.91(d, J=9.6Hz, 1H), 7.80(d, J=9.6Hz, 1H ), 7.63(dd, J=9.6, 1.8Hz, 1H), 7.39(dd, J=9.6, 1.8Hz, 1H), 3.64(q, J=7.5Hz, 2H), 1.31(t, J=7.5Hz , 3H).
1-6-001a δ9.38(d, J=7.5Hz, 1H), 9.24(s, 1H), 8.66(s, 1H), 8.62(s, 1H), 8.13-8.08(m, 1H), 7.26 (dd, J=7.5, 1.9Hz, 1H), 3.74(q, J=7.4Hz, 2H), 1.35(t, J=7.4Hz, 3H).
1-6-002a δ9.63(s, 1H), 9.24(s, 1H), 8.68(s, 1H), 8.62(s, 1H), 7.93(d, J=9.3Hz, 1H), 7.66(dd , J=9.3, 1.8Hz, 1H), 3.70(q, J=7.5Hz, 2H), 1.35(t, J=7.5Hz, 3H).
1-7-001a δ9.42(d, J=7.5Hz, 1H), 8.15(d, J=1.7Hz, 1H), 7.96(d, J=8.2Hz, 1H), 7.75(d, J=8.2 Hz, 1H), 7.32(dd, J=7.5, 1.7Hz, 1H), 4.23(q, J=7.4Hz, 2H), 4.14(s, 3H), 1.46(t, J=7.4Hz, 3H).
1-8-002a δ9.63(s, 1H), 9.00(s, 1H), 8.15(s, 1H), 7.95(d, J=9.6Hz, 1H), 7.73(dd, J=9.6, 1.5Hz , 1H), 4.19(s, 3H), 4.06(q, J=7.5Hz, 2H), 1.47(t, J=7.5Hz, 3H).
1-8-002b δ9.03(s, 1H), 8.97(s, 1H), 8.20(s, 1H), 7.82(d, J=9.6Hz, 1H), 7.54(dd, J=9.6, 1.5Hz , 1H), 4.36(s, 3H), 3.15(q, J=7.5Hz, 2H), 1.23(t, J=7.5Hz, 3H).
1-8-006a δ9.17(d, J=7.5Hz, 1H), 8.99(s, 1H), 8.14(s, 1H), 7.84(d, J=2.4Hz, 1H), 7.15(dd, J =7.5, 2.4Hz, 1H), 4.17(s, 3H), 3.99(q, J=7.5Hz, 2H), 1.43(t, J=7.5Hz, 3H).
1-8-006b δ8.95(s, 1H), 8.59(d, J=7.5Hz, 1H), 8.19(s, 1H), 7.74-7.71(m, 1H), 7.03(dd, J=7.5, 2.1Hz, 1H), 4.33(s, 3H), 3.09(q, J=7.5Hz, 2H), 1.19(t, J=7.5Hz, 3H).
1-8-007a δ9.47(s, 1H), 8.98(s, 1H), 8.14(s, 1H), 7.76(dd, J=9.3, 1.2Hz, 1H), 7.61(d, J=9.3Hz , 1H), 4.15(s, 3H), 3.98(q, J=7.5Hz, 2H), 1.45(t, J=7.5Hz, 3H).
1-8-007b δ8.95(s, 1H), 8.90(s, 1H), 8.19(s, 1H), 7.57(dd, J=9.3, 1.2Hz, 1H), 7.50(d, J=9.3, Hz, 1H), 4.33(s, 3H), 3.10(q, J=7.5Hz, 2H), 1.21(t, J=7.5Hz, 3H).
1-8-008a δ9.32-9.31(m, 1H), 8.99(s, 1H), 8.14(d, J=1.2Hz, 1H), 7.53(dd, J=8.3, 1.2Hz, 1H), 4.19 (s, 3H), 4.05(q, J=7.5Hz, 2H), 1.46(t, J=7.5Hz, 3H).
1-8-009a δ8.88(d, J=1.4Hz, 1H), 8.85(s, 1H), 7.99-7.97(m, 1H), 6.94(d, J=1.4Hz, 1H), 4.20(q , J=7.0Hz, 2H), 3.99(s, 3H), 3.76(q, J=7.4Hz, 2H), 1.47(t, J=7.0Hz, 3H), 1.30(t, J=7.4Hz, 3H ).
1-8-010a δ9.00-8.90(m, 2H), 8.30-8.25(m, 1H), 8.15-8.10(m, 1H), 7.40(dd, J=7.4, 1.6Hz, 1H), 4.15( s, 3H), 3.98(q, J=7.4Hz, 2H), 1.43(t, J=7.4Hz, 3H).
1-8-011a δ9.25-9.20(m, 1H), 9.00-8.95(m, 1H), 8.15-8.10(m, 1H), 7.43(dd, J=8.6, 1.6Hz, 1H), 4.20( s, 3H), 4.12(q, J=7.4Hz, 2H), 1.47(t, J=7.4Hz, 3H).
1-8-013a δ9.39(dd, J=1.7.0.7Hz, 1H), 8.99(s, 1H), 8.14(d, J=0.7Hz, 1H), 7.74(dd, J=9.5, 0.7Hz , 1H), 7.66(dd, J=9.5, 1.7Hz, 1Hz), 4.17(s, 3H), 4.01(q, J=7.5Hz, 2H), 1.47(t, J=7.5Hz, 3H).
1-8-013b δ8.95(s, 1H), 8.80(dd, J=9.5, 2.0Hz, 1H), 8.19(d, J=0.9Hz, 1H), 7.62(dd, J=9.5, 0.9Hz , 1H), 7.46(dd, J=9.5, 2.0Hz, 1H), 4.35(s, 3H), 3.11(q, J=7.4Hz, 2H), 1.22(t, J=7.4Hz, 3H).
1-8-013c δ9.65(dd, J=1.9, 0.9Hz, 1H), 8.97(s, 1H), 8.10(d, J=0.9Hz, 1H), 7.66(dd, J=9.5, 0.9Hz , 1H), 7.52(dd, J=9.7, 1.9Hz, 1H), 4.49(s, 3H), 3.77-3.64(m, 1H), 3.63-3.52(m, 1H), 1.58(t, J=7.3 Hz, 3H).
1-8-014a δ 9.68 (s, 1H), 9.02 (s, 1H), 8.20 (s, 1H), 8.15 (s, 1H), 4.20 (s, 3H), 4.12 (q, J=7.2Hz , 2H), 1.48 (t, J=7.2Hz, 3H).
1-8-014b δ 9.04 (s, 1H), 9.00 (s, 1H), 8.18 (s, 1H), 8.13 (s, 1H), 4.37 (s, 3H), 3.19 (q, J=7.3 Hz , 2H), 1.23 (t, J=7.3 Hz, 3H).
1-8-015a δ9.55 (d, J=6.1 Hz, 1H), 9.00 (s, 1H), 8.14 (s, 1H), 7.52 (d, J=7.4 Hz, 1H), 4.18 (s, 3H ), 4.03 (q, J=7.4 Hz, 2H), 1.46 (t, J = 7.4 Hz, 3H).
1-8-015b δ8.96-8.92 (m, 2H), 8.19-8.18 (m, 1H), 7.40 (d, J=8.2Hz, 1H), 4.34 (s, 3H), 3.11 (q, J= 7.4Hz, 2H), 1.22 (t, J=7.3Hz, 3H).
1-8-016a δ9.29(d, J=2.0Hz, 1H), 9.00-8.95(m, 1H), 8.15-8.10(m, 1H), 7.78(d, J=9.5Hz, 1H), 7.55 (dd, J=9.5, 2.0Hz, 1H), 4.16(s, 3H), 4.00(q, J=7.4Hz, 2H), 1.45(t, J=7.4Hz, 3H).
1-8-016b δ8.95-8.90(m, 1H), 8.68(d, J=2.0Hz, 1H), 8.20-8.15(m, 1H), 7.66(d, J=9.4Hz, 1H), 7.36 (dd, J=9.4, 2.0Hz,1H), 4.34(s, 3H), 3.10(q, J=7.4Hz, 2H), 1.21(t, J=7.4Hz, 3H).
1-9-001a δ9.63(s, 1H), 9.21(s, 1H), 7.95(d, J=9.6Hz, 1H), 7.85(s, 1H), 7.72(d, J=9.6Hz, 1H ), 4.11(s, 3H), 4.06(q, J=7.5Hz, 2H), 1.47(t, J=7.5Hz, 3H).
1-9-001b δ 9.26(s, 1H), 9.03(s, 1H), 7.83(s, 1H), 7.82(d, J=9.6Hz, 1H), 7.54(d, J=9.6Hz, 1H ), 4.29(s, 3H), 3.16(q, J=7.5Hz, 2H), 1.23(t, J=7.5Hz, 3H).
1-9-002a δ9.39(d, J=7.8Hz, 1H), 9.20(s, 1H), 8.14(s, 1H), 7.85(s, 1H), 7.32(dd, J=7.8, 1.5Hz , 1H), 4.12(s, 3H), 4.07(q, J=7.5Hz, 2H), 1.46(t, J=7.5Hz, 3H).
1-9-002b δ9.25(s, 1H), 8.77(d, J=7.2Hz, 1H), 8.04(s, 1H), 7.82(s, 1H), 7.20(dd, J=7.2, 1.2Hz , 1H), 4.29(s, 3H), 3.16(q, J=7.5Hz, 2H), 1.22(t, J=7.5Hz, 3H).
1-9-003a δ9.19(s, 1H), 9.17(d, J=7.5Hz, 1H), 7.85-7.81(m, 2H), 7.14(dd, J=7.5, 2.4Hz, 1H), 4.08 (s, 3H), 4.00(q, J=7.5Hz, 2H), 1.44(t, J=7.5Hz, 3H).
1-9-003b δ9.24(s, 1H), 8.59(dd, J=7.2, 0.6Hz, 1H), 7.81(s, 1H), 7.73-7.69(m, 1H), 7.03(dd, J= 7.2, 1.8Hz, 1H), 4.26(s, 3H), 3.10(q, J=7.5Hz, 2H), 1.20(t, J=7.5Hz, 3H).
1-10-001a δ9.44(d, J=7.2Hz, 1H), 8.86(d, J=0.7Hz, 1H), 8.12-8.04(m, 2H), 7.87(d, J=8.9Hz, 1H ), 7.33-7.28(m, 2H), 4.08(q, J=7.5Hz, 2H), 1.47(t, J=7.5Hz, 3H).
1-10-001b δ9.08(d, J=0.7Hz, 1H), 8.75(d, J=7.2Hz, 1H), 8.20-8.17(m, 1H), 8.00-7.97(m, 1H), 7.87 (d, J=8.9Hz, 1H), 7.29(dd, J=8.9, 1.4Hz, 1H), 7.22(dd, J=7.2, 1.9Hz, 1H), 3.00(q, J=7.4Hz, 2H) , 1.20(t, J=7.4Hz, 3H).
1-10-001c δ9.57(d, J=7.2Hz, 1H), 8.99(d, J=1.0Hz, 1H), 8.09-8.05(m, 1H), 8.01-7.97(m, 1H), 7.87 (d, J=8.9Hz, 1H), 7.31(dd, J=8.9, 1.4Hz, 1H), 7.16(dd, J=7.2, 1.9Hz, 1H), 3.73-3.46(m, 2H), 1.55( t, J=7.5Hz, 3H).
1-10-002c δ9.57(d, J=7.4Hz, 1H), 9.30(d, J=0.9Hz, 1H), 8.85(d, J=1.5Hz, 1H), 8.44-8.41(m, 1H ), 8.05-8.02(m, 1H), 7.19(dd, J=7.4, 2.3Hz, 1H), 3.70-3.43(m, 2H), 1.55(t, J=7.4Hz, 3H).
1-10-003a δ9.52-9.50(m, 1H), 9.13-9.12(m, 1H), 8.86-8.84(m, 1H), 8.45-8.43(m, 1H), 7.80(dd, J=9.2 , 1.5Hz, 1H), 7.58(dd, J=9.2, 0.9Hz, 1H), 3.97(q, J=7.5Hz, 2H), 1.48(t, J=7.5Hz, 3H).
1-10-003b δ9.40(s, 1H), 8.86-8.85(m, 1H), 8.83(d, J=2.1Hz, 1H), 8.50-8.48(m, 1H), 7.62(dd, J= 9.2, 1.5Hz, 1H), 7.51(d, J=9.2Hz, 1H), 2.94(q, J=7.4Hz, 2H), 1.20(t, J=7.4Hz, 3H).
1-11-001cδ 9.58(d, J=7.4Hz, 1H), 9.38(s, 1H), 9.23(d, J=0.9Hz, 1H), 8.06(s, 1H), 8.04-8.01(m, 1H), 7.25-7.17(m, 1H), 3.75-3.45(m, 2H), 1.53(t, J=7.4Hz, 3H).
1-11-002a δ9.40-9.35(m, 1H), 9.05-9.00(m, 1H), 8.99(d, J=7.4Hz, 1H), 8.25-8.20(m, 1H), 8.10-8.05( m, 1H), 7.43(dd, J=7.4, 1.8Hz, 1H), 3.95(q, J=7.4Hz, 2H), 1.44(t, J=7.4Hz, 3H).
1-11-003a δ9.51-9.48(m, 1H), 9.38(s, 1H), 9.03-9.01(m, 1H), 8.07(s, 1H), 7.81(dd, J=9.3, 1.7Hz, 1H), 7.58(d, J=9.3Hz, 1H), 3.95(q, J=7.4Hz, 2H), 1.47(t, J=7.4Hz, 3H).
1-11-003b δ9.36(s, 1H), 9.27(s, 1H), 8.87-8.85(m, 1H), 8.13(s, 1H), 7.62(dd, J=9.2, 0.9Hz, 1H) , 7.49(d, J=9.2Hz, 1H), 2.97(q, J=7.4Hz, 2H), 1.20(t, J=7.4Hz, 3H).
1-11-004a δ9.69-9.66(m, 1H), 9.40(d, J=1.0Hz, 1H), 9.08(d, J=1.0Hz, 1H), 8.09(s, 1H), 7.93(d , J=9.5Hz, 1H), 7.78(dd, J=9.5, 1.7Hz, 1H), 4.03(q, J=7.5Hz, 2H), 1.50(t, J=7.5Hz, 3H).
1-11-004b δ9.38(dd, J=1.4, 0.7Hz, 1H), 9.30(d, J=1.0Hz, 1H), 9.02-8.99(m, 1H), 8.15(s, 1H), 7.85 -7.80(m, 1H), 7.60(dd, J=9.3, 1.7Hz, 1H), 3.03(q, J=7.4Hz, 2H), 1.23(t, J=7.4Hz, 3H).
1-11-004c δ9.87-9.85(m, 1H), 9.38(s, 1H), 9.23(d, J=1.0Hz, 1H), 8.05(s, 1H), 7.83(d, J=9.5Hz , 1H), 7.64(dd, J=9.5, 1.7Hz, 1H), 3.72-3.47(m, 2H), 1.57(t, J=7.5Hz, 3H).
1-11-005a δ9.40-9.35(m, 1H), 9.30-9.25(m, 1H), 9.10-9.05(m, 1H), 8.06(s, 1H), 7.48(dd, J=8.6, 1.6 Hz, 1H), 4.02(q, J=7.4Hz, 2H), 1.49(t, J=7.4Hz, 3H).
1-11-005b δ9.40-9.30(m, 1H), 9.25(d, J=1.0Hz, 1H), 8.65-8.60(m, 1H), 8.15-8.10(m, 1H), 7.30(dd, J=8.9, 1.7Hz, 1H), 3.04(q, J=7.4Hz, 2H), 1.23(t, J=7.4Hz, 3H).
1-11-006a δ9.39-9.37(m, 1H), 9.35(s, 1H), 9.08(d, J=1.4Hz, 1H), 8.07(s, 1H), 7.58(dd, J=8.2, 1.4Hz, 1H), 4.03(q, J=7.5Hz, 2H), 1.50(t, J=7.5Hz, 3H).
1-11-006b δ9.36(s, 1H), 9.27(s, 1H), 8.72(d, J=1.4Hz, 1H), 8.14(s, 1H), 7.40(dd, J=8.9, 1.4Hz , 1H), 3.05(q, J=7.5Hz, 2H), 1.23(t, J=7.5Hz, 3H).
1-11-007a δ9.42-9.41(m, 1H), 9.39-9.37(m, 1H), 9.03(d, J=1.0Hz, 1H), 8.08(s, 1H), 7.71-7.69(m, 2H), 3.96(q, J=7.5Hz, 2H), 1.48(t, J=7.5Hz, 3H).
1-11-007b δ9.38-9.36(m, 1H), 9.27(d, J=1.0Hz, 1H), 8.77(d, J=1.0Hz, 1H), 8.14(s, 1H), 7.61(d , J=9.5Hz, 1H), 7.52(dd, J=9.5, 1.9Hz, 1H), 2.98(q, J=7.4Hz, 2H), 1.22(t, J=7.4Hz, 3H).
1-11-007c δ9.58(d, J=1.0Hz, 1H), 9.37(s, 1H), 9.19(s, 1H), 8.05(s, 1H), 7.62(d, J=9.5Hz, 1H ), 7.56(dd, J=9.5, 1.4Hz, 1H), 3.71-3.44(m, 2H), 1.56(t, J=7.3Hz, 3H).
1-12-002a δ9.59(s, 1H), 8.45(s, 1H), 7.94-7.92(m, 1H), 7.86(d, J=9.6Hz, 1H), 7.61(dd, J=9.6, 2.1Hz, 1H), 3.60(q, J=7.5Hz, 2H), 1.31(t, J=7.5Hz, 3H).
1-12-003a δ9.62(s, 1H), 8.30(s, 1H), 7.85(d, J=9.6Hz, 1H), 7.61(dd, J=9.6, 1.5Hz, 1H), 3.69(q , J=7.5Hz, 2H), 2.61(s, 3H), 1.32(t, J=7.5Hz, 3H).
1-12-004a δ9.35(d, J=7.5Hz, 1H), 8.42(s, 1H), 8.04(s, 1H), 7.96(d, J=1.7Hz, 1H), 7.20(dd, J =7.5, 1.7Hz, 1H), 3.62(q, J=7.4Hz, 2H), 1.30(t, J=7.4Hz, 3H).
1-12-005a δ9.37(d, J=7.5Hz, 1H), 8.28(s, 1H), 8.04-8.02(m, 1H), 7.20(dd, J=7.5, 1.9Hz, 1H), 3.72 (q, J=7.4Hz, 2H), 2.63(s, 3H), 1.32(t, J=7.4Hz, 3H).
1-12-006a δ9.61(s, 1H), 8.78(s, 1H), 7.87(d, J=9.6Hz, 1H), 7.63(dd, J=9.6, 1.8Hz, 1H), 3.63(q , J=7.5Hz, 2H), 1.33(t, J=7.5Hz, 3H).
1-12-007a δ9.60(s, 1H), 8.81(s, 1H), 7.87(d, J=9.6Hz, 1H), 7.63(dd, J=9.6, 1.8Hz, 1H), 3.62(q , J=7.5Hz, 2H), 1.33(t, J=7.5Hz, 3H).
1-12-008a δ9.35(d, J=7.5Hz, 1H), 8.77(s, 1H), 8.08-8.04(m, 1H), 7.22(dd, J=7.5, 1.9Hz, 1H), 3.64 (q, J=7.4Hz, 2H), 1.32(t, J=7.4Hz, 3H).
1-12-009a δ9.43(dd, J=1.5, 0.9Hz, 1H), 8.77(s, 1H), 7.67(dd, J=9.4, 1.5Hz, 1H), 7.56(dd, J=9.4, 0.9Hz, 1H), 3.56(q, J=7.5Hz, 2H), 1.32(t, J=7.5Hz, 3H).
1-12-010a δ9.66-9.61 (m, 1H), 7.84 (d, J=9.2Hz, 1H), 7.61 (dd, J=9.2, 1.9 Hz, 1H), 3.99 (q, J=7.5Hz , 2H), 2.87 (s, 3H), 1.41 (t, J=7.5Hz, 3H).
1-15-002a δ9.43(d, J=7.5Hz, 1H), 8.15-8.12(m, 1H), 7.79(s, 1H), 7.73(s, 1H), 7.31(dd, J=7.5, 1.9Hz, 1H), 4.27(q, J=7.4Hz, 2H), 4.14(s, 3H), 1.50(t, J=7.4Hz, 3H).
1-15-002b δ8.79(d, J=7.4Hz, 1H), 8.02(s, 1H), 7.77(s, 1H), 7.70(s, 1H), 7.19(dd, J=7.4, 1.7Hz , 1H), 4.26(s, 3H), 3.35(q, J=7.4Hz, 2H), 1.29(t, J=7.4Hz, 3H).
1-15-003a δ9.35(d, J=7.5Hz, 1H), 8.15(s, 1H), 8.04(s, 1H), 7.76(s, 1H), 7.36-7.29(m, 1H), 4.31 (s, 3H), 3.98(q, J=7.4Hz, 2H), 1.44(t, J=7.4Hz, 3H).
1-17-001a δ9.46(s, 1H), 8.85-8.81(m, 1H), 8.78(d, J=2.4Hz, 1H), 7.70(dd, J=9.6, 1.5Hz, 1H), 7.62 (d, J=9.3Hz, 1H), 4.05(q, J=7.5Hz, 2H), 1.45(t, J=7.5Hz, 3H).
2-1-001a δ8.76-8.73(m, 1H), 8.71-8.67(m, 1H), 8.35-8.32(m, 1H), 4.22(s, 3H), 4.19(q, J=7.4Hz, 2H), 1.45(t, J=7.4Hz, 3H).
2-1-001b δ8.66-8.64(m, 1H), 8.36-8.34(m, 1H), 8.11-8.09(m, 1H), 4.24(s, 3H), 3.14(q, J=7.4Hz, 2H), 1.25(t, J=7.4Hz, 3H).
3-1-001c δ8.83(d, J=1.4Hz, 1H), 8.57(brs, 1H), 8.41(d, J=1.7Hz, 1H), 7.72(dd, J=8.9, 1.4Hz, 1H ), 7.63(d, J=8.9Hz, 1H), 4.00(s, 3H), 3.82(s, 3H), 3.41-3.09(m, 2H), 1.19(t, J=7.3Hz, 3H).
3-1-002c δ9.16(s, 1H), 8.78(s, 1H), 8.36(s, 1H), 8.10(d, J=8.6Hz, 1H), 7.79(d, J=8.6Hz, 1H ), 4.12(s, 3H), 3.64-3.46(m, 2H), 1.49(t, J=7.5Hz, 3H).
i-1-012 δ8.03(d, J=1.8Hz, 1H), 7.58(d, J=9.9Hz, 1H), 7.40(d, J=2.4Hz, 1H), 4.48(q, J=7.2 Hz, 2H), 3.89(s, 3H), 2.94(q, J=7.2Hz, 2H), 1.46(t, J=7.5Hz, 3H), 1.19(t, J=7.5Hz, 3H).
i-1-020 δ8.29(d, J=6.6Hz, 1H), 8.10(d, J=0.9Hz, 1H), 7.21(dd, J=7.2, 1.5Hz, 1H), 4.49(q, J =7.2Hz, 2H), 2.93(q, J=7.2Hz, 2H), 1.47(t, J=7.5Hz, 3H), 1.18(t, J=7.5Hz, 3H).
i-1-025 δ8.73(d, J=1.4Hz, 1H), 7.62(d, J=1.4Hz, 1H), 4.51(q, J=7.0Hz, 2H), 2.97(q, J=7.4 Hz, 2H), 1.37(t, J=7.0Hz, 3H), 1.21(t, J=7.4Hz, 3H).
i-1-032 δ8.66(dd, J=7.2, 0.9Hz, 1H), 8.15-8.10(m, 1H), 7.12(dd, J=7.2, 1.7Hz, 1H), 4.52(q, J= 7.2Hz, 2H), 3.00(q, J=7.4Hz, 2H), 1.48(t, J=7.2Hz, 3H), 1.20(q, J=7.4Hz, 3H).
i-1-033 δ8.98(dd, J=7.5, 0.6Hz, 1H), 8.23(dd, J=1.5, 0.6Hz, 1H), 7.33(dd, J=7.5, 1.5Hz, 1H), 4.52 (q, J=7.2Hz, 2H), 3.71(q, J=7.2Hz, 2H), 1.47(t, J=7.2Hz, 3H), 1.35(t, J=7.2Hz, 3H).
i-1-034 δ9.08(d, J=7.2Hz, 1H), 8.60-8.57(m, 1H), 7.41(dd, J=7.2, 1.5Hz, 1H), 3.85(q, J=7.2Hz , 2H), 1.36(t, J=7.2Hz, 3H).
i-1-035 δ8.90(d, J=7.2Hz, 1H), 6.76(s, 1H), 6.58-6.48(m, 1H), 4.48(q, J=7.2Hz, 2H), 4.45(brs , 2H), 3.65(q, J=7.2Hz, 2H), 1.45(t, J=7.2Hz, 3H), 1.33(t, J=7.2Hz, 3H).
i-1-036 δ8.27(d, J=7.4Hz, 1H), 6.75-6.65(m, 1H), 6.46(dd, J=7.4, 1.6Hz, 1H), 4.46(q, J=7.0Hz , 2H), 4.20-4.05(brs, 2H), 2.87(q, J=7.4Hz, 2H), 1.44(t, J=7.0Hz, 3H), 1.17(t, J=7.4Hz, 3H).
i-1-037 δ8.35(d, J=6.6Hz, 1H), 6.62(d, J=6.6Hz, 1H), 6.61(s, H), 3.43(q, J=7.5Hz, 2H), 1.91(t, J=7.5Hz, 3H) (NH ₂ and CO ₂ H proton peaks could not be observed).
i-1-038 δ9.12(d, J=8.1Hz, 1H), 8.06(s, 1H), 7.63-7.58(m, 1H), 7.34(d, J=8.1Hz, 1H), 4.51(q , J=7.2Hz, 2H), 3.70(q, J=7.2Hz, 2H), 2.25(s, 3H), 1.47(t, J=7.2Hz, 3H), 1.34(t, J=7.2Hz, 3H ).
i-3-041 δ8.70-8.65(m, 1H), 8.54(s, 1H), 8.50-8.40(m, 1H), 8.30-8.20(m, 2H), 7.51(dd, J=7.2, 1.4 Hz, 1H), 4.48(s, 3H), 4.00(s, 3H).
i-3-042 δ13.50-13.40(brs, 1H), 8.95(s, 1H), 8.75(s, 1H), 8.74(d, J=7.0Hz, 1H), 8.51(s, 1H), 8.23 (s, 1H), 7.45(d, J=7.0Hz, 1H), 4.38(s, 3H).
i-3-043 δ8.70-8.65(m, 1H), 8.44(s, 1H), 8.30-8.20(m, 2H), 7.70(d, J=8.6Hz, 1H), 7.35-7.25(m, 1H), 6.91(dd, J=6.3, 6.3Hz, 1H), 4.47(s, 3H).
i-3-045 δ8.70-8.60(m, 1H), 8.35(s, 1H), 8.23(d, J=2.0Hz, 1H), 7.68(dd, J=6.5, 0.8Hz, 1H), 6.72 (dd, J=7.4, 6.5Hz, 1H), 6.40 (dd, J=7.4, 0.8Hz, 1H), 4.65-4.55(brs, 2H), 4.46(s, 3H).
i-3-046 δ8.70-8.60(m, 1H), 8.32(s, 1H), 8.25-8.20(m, 1H), 7.47(d, J=7.0Hz, 1H), 7.01(d, J= 7.0Hz, 1H), 5.05-4.95(brs, 2H), 4.30(s, 3H).
i-3-048 δ8.89(s, 1H), 8.76(s, 1H), 8.71(d, J=7.0Hz, 1H), 8.51(s, 1H), 8.32 (s, 1H), 8.30-8.20 (brs, 1H), 7.70-7.60(brs, 1H), 7.47(d, J=7.0Hz, 1H), 4.38(s, 3H).
i-5-005 δ9.13(brs, 1H), 8.37(s, 1H), 7.91(s, 1H), 7.87(d, J=8.9Hz, 1H), 7.58(d, J=6.8Hz, 1H ), 7.46-7.40(m, 1H), 5.24(brs, 1H), 3.10(d, J=4.8Hz, 3H), 3.06(q, J=7.5Hz, 2H), 1.27(t, J=7.5Hz , 3H).
i-7-003 δ7.95(d, J=7.0Hz, 1H), 7.69(s, 1H), 7.04(d, J=7.0Hz, 1H), 4.35(brs, 2H), 2.58(q, J =7.4Hz, 2H), 1.19(t, J=7.4Hz, 3H).
i-7-004 δ8.56(s, 1H), 7.42(d, J=9.2Hz, 1H), 7.32(dd, J=9.2, 1.7Hz, 1H), 4.42(brs, 2H), 2.65(q , J=7.3Hz, 2H), 1.24(t, J=7.3Hz, 3H).
i-7-005 δ8.17(d, J=1.6Hz, 1H), 7.04(dd, J=9.4, 1.6Hz, 1H), 4.38(brs, 2H), 2.63(q, J=7.4Hz, 2H ), 1.22(t, J=7.4Hz, 3H).
i-8-012 δ 8.79 (d, J=2.0Hz, 1H), 8.53 (d, J=2.0Hz, 1H), 7.14 (s, 1H), 4.25 (s, 3H), 3.03-2.79 (m , 2H), 1.39 (t, J=7.5Hz, 3H).
i-8-014 δ8.91-8.88 (m, 1H), 8.70 (d, J=2.4Hz, 1H), 4.85 (s, 2H), 4.28 (s, 3H).
i-8-015 δ8.86 (d, J=1.5Hz, 1H), 8.67 (d, J=1.5Hz, 1H), 4.27 (s, 3H), 4.07 (s, 2H), 2.66 (q, J =7.4Hz, 2H), 1.31 (t, J=7.4Hz, 3H).
i-8-016 δ8.91-8.86 (m, 1H), 8.72-8.66 (m, 1H), 7.15-7.10 (m, 0.7H), 4.85 (s, 0.3H), 4.31-4.26 (m, 3H ), 3.03-2.79 (m, 2H), 1.43-1.34 (m, 3H).
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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 thereto.

Test Example 1: Insecticidal test against brown planthopper A 10% emulsion of the compound of the present invention (10% wettable powder was used depending on the compound) was diluted with water containing a spreading agent to prepare a drug solution having a concentration of 500 ppm. A rice leaf sheath was immersed in the drug solution for about 10 seconds. After the dipping operation was completed, the leaf pods of the rice treated with the chemical solution were air-dried and then put into a test tube. Five third-instar larvae of the brown planthopper (Nilaparvata lugens) were released in each test tube, covered with a sponge, and housed in a thermostatic chamber at 25°C. Six days after housing, the number of dead planthoppers in the test tube was examined, and the mortality rate (%) (number of dead insects/number of test insects×100) was calculated. The test was carried out in a double loop.

As a result, among the tested compounds, the following compounds showed a mortality of 90% or more.
Inventive compound: 1-1-001a, 1-1-002a, 1-1-005a, 1-1-006a, 1-1-009a, 1-1-015a, 1-1-020a, 1-1- 023a, 1-1-024a, 1-1-035a, 1-1-036a, 1-1-038a, 1-1-039a, 1-1-040a, 1-1-042a, 1-1-043a, 1-1-044a, 1-1-049a, 1-1-052a, 1-1-057a, 1-1-057c, 1-1-058a, 1-1-064a, 1-1-072a, 1- 1-074a, 1-1-095a, 1-1-096a, 1-1-097a, 1-1-099a, 1-1-100a, 1-1-105a, 1-1-106a, 1-1- 116a, 1-1-117a, 1-1-122a, 1-1-123a, 1-1-124a, 1-1-125a, 1-1-138a, 1-1-166a, 1-1-170a, 1-1-171a, 1-1-173a, 1-1-182a, 1-1-183a, 1-1-183b, 1-1-185a, 1-1-189a, 1-1-190a, 1- 1-191a, 1-1-192a, 1-1-193a, 1-1-196a, 1-1-197a, 1-1-198a, 1-2-001a, 1-2-002a, 1-3 001a, 1-3-003a, 1-3-005a, 1-3-007a, 1-4-002a, 1-5-002a, 1-8-002a, 1-8-005a, 1-8-010a, 1-8-016a, 1-9-002a, 1-11-001a, 1-11-001b, 1-11-002a, 1-11-003a, 1-11-004a, 1-11-004b, 1- 11-008a, 1-11-009a, 1-12-003a, 1-12-004a, 1-12-006a, 1-12-007a, 1-12-008a, 1-12-009a, 1-12- 012a, 1-14-001a, 1-16-001a, 1-16-001b, 2-1-001a, 3-1-002a
Test Example 2: Insecticidal test against diamondback moth A 10% emulsion of the compound of the present invention (a 10% wettable powder was used depending on the compound) was diluted with water containing a spreading agent to prepare a drug solution having a concentration of 500 ppm. A leaf of kanran was immersed in the chemical solution for about 10 seconds. After the dipping operation was completed, the chemical solution-treated kanran leaf was air-dried and then placed in a petri dish. Five third-instar larvae of diamondback moth (Plutella xylostella) were released in each dish, covered with a lid, and stored in a thermostatic chamber at 25°C. Six days after storage, the number of dead larvae of diamondback moth in the petri dish was examined, and the mortality rate was calculated from the same formula as in Test Example 1. The test was carried out in a double loop.

As a result, among the tested compounds, the following compounds showed a mortality of 90% or more.
The compound of the present invention: 1-1-001a, 1-1-001b, 1-1-001c, 1-1-002a, 1-1-002b, 1-1-003a, 1-1-003c, 1-1- 004a, 1-1-005a, 1-1-005c, 1-1-006a, 1-1-007a, 1-1-008a, 1-1-009a, 1-1-011a, 1-1-012a, 1-1-012b, 1-1-013a, 1-1-013b, 1-1-013c, 1-1-014a, 1-1-014b, 1-1-014c, 1-1-015a, 1- 1-015b, 1-1-016a, 1-1-016b, 1-1-016c, 1-1-017a, 1-1-018a, 1-1-019a, 1-1-020a, 1-1- 020b, 1-1-021b, 1-1-022a, 1-1-023a, 1-1-023b, 1-1-023c, 1-1-024a, 1-1-026a, 1-1-027a, 1-1-027b, 1-1-029a, 1-1-030a, 1-1-030b, 1-1-030c, 1-1-032a, 1-1-033a, 1-1-034a, 1- 1-035a, 1-1-036a, 1-1-037a, 1-1-038a, 1-1-039a, 1-1-040a, 1-1-040c, 1-1-041a, 1-1- 042a, 1-1-043a, 1-1-044a, 1-1-045a, 1-1-045b, 1-1-046a, 1-1-047a, 1-1-048a, 1-1-049a, 1-1-049b, 1-1-050a, 1-1-050b, 1-1-051a, 1-1-051b, 1-1-052a, 1-1-052b, 1-1-053a, 1- 1-054a, 1-1-055a, 1-1-056a, 1-1-057a, 1-1-057c, 1-1-058a, 1-1-058b, 1-1-059a, 1-1- 060a, 1-1-060b, 1-1-061a, 1-1-062a, 1-1-063a, 1-1-063b, 1-1-064a, 1-1-065a, 1-1-066a, 1-1-067a, 1-1-068a, 1-1-069a, 1-1-069b, 1-1-070a, 1-1-070b, 1-1-071a, 1-1-072a, 1- 1-072b, 1-1-072c, 1-1-073b, 1-1-074a, 1-1-076a, 1-1-077a, 1-1-077b, 1-1-080a, 1-1- 081a, 1-1-082a, 1-1-083a, 1-1 -084a, 1-1-085a, 1-1-086a, 1-1-087a, 1-1-088a, 1-1-089a, 1-1-090a, 1-1-091a, 1-1-092a , 1-1-093a, 1-1-093b, 1-1-094a, 1-1-094b, 1-1-094c, 1-1-095a, 1-1-096a, 1-1-097a, 1 -1-099a, 1-1-100a, 1-1-101a, 1-1-101b, 1-1-103a, 1-1-103b, 1-1-104a, 1-1-105a, 1-1 -105b, 1-1-105c, 1-1-106a, 1-1-106b, 1-1-106c, 1-1-107a, 1-1-108a, 1-1-109a, 1-1-109b , 1-1-110a, 1-1-110c, 1-1-111a, 1-1-112a, 1-1-112b, 1-1-113a, 1-1-113b, 1-1-114a, 1 -1-114b, 1-1-115a, 1-1-115b, 1-1-116a, 1-1-117a, 1-1-118a, 1-1-118c, 1-1-120c, 1-1 -121a, 1-1-122a, 1-1-123a, 1-1-124a, 1-1-124b, 1-1-125a, 1-1-126a, 1-1-127a, 1-1-128a , 1-1-130a, 1-1-131a, 1-1-132a, 1-1-133a, 1-1-134a, 1-1-135a, 1-1-136a, 1-1-137a, 1 -1-138a, 1-1-139a, 1-1-139b, 1-1-140a, 1-1-141a, 1-1-142a, 1-1-142b, 1-1-143a, 1-1 -144a, 1-1-145a, 1-1-145b, 1-1-146a, 1-1-147a, 1-1-148a, 1-1-149a, 1-1-150a, 1-1-151a , 1-1-152a, 1-1-153a, 1-1-153b, 1-1-154a, 1-1-155a, 1-1-156a, 1-1-157a, 1-1-158a, 1 -1-159a, 1-1-160a, 1-1-161a, 1-1-162a, 1-1-163a, 1-1-164a, 1-1-165a, 1-1-166a, 1-1 -167a, 1-1-168a, 1-1-169a, 1-1-170a, 1-1-171a, 1-1-171b, 1-1-172a, 1-1-173a, 1-1-174a , 1-1-175a, 1-1-176a, 1-1- 177a, 1-1-178a, 1-1-179a, 1-1-180a, 1-1-181a, 1-1-182a, 1-1-183a, 1-1-183b, 1-1-185a, 1-1-186a, 1-1-187a, 1-1-188a, 1-1-189a, 1-1-190a, 1-1-191a, 1-1-192a, 1-1-193a, 1- 1-194a, 1-1-195a, 1-1-196a, 1-1-197a, 1-1-198a, 1-1-199a, 1-2-001a, 1-2-002a, 1-2- 004a, 1-2-004b, 1-2-004c, 1-2-005a, 1-2-006a, 1-3-001a, 1-3-002a, 1-3-003a, 1-3-004a, 1-3-005a, 1-3-006a, 1-3-007a, 1-3-008a, 1-3-009a, 1-3-010a, 1-3-011a, 1-3-012a, 1- 3-013a, 1-3-014a, 1-3-015a, 1-4-001a, 1-4-002a, 1-4-003a, 1-4-003b, 1-4-004a, 1-5- 001a, 1-5-002a, 1-5-003a, 1-5-004a, 1-6-001a, 1-6-002a, 1-7-001a, 1-8-001b, 1-8-002a, 1-8-002b, 1-8-003a, 1-8-003b, 1-8-004b, 1-8-005a, 1-8-005b, 1-8-006a, 1-8-006b, 1- 8-007a, 1-8-008a, 1-8-009a, 1-8-010a, 1-8-011a, 1-8-013a, 1-8-013b, 1-8-014a, 1-8- 014b, 1-8-015a, 1-8-015b, 1-8-016a, 1-9-002a, 1-9-002b, 1-9-003a, 1-9-003b, 1-10-001a, 1-10-001b, 1-10-001c, 1-10-002a, 1-10-002b, 1-10-002c, 1-10-003a, 1-10-004a, 1-10-005a, 1- 10-006a, 1-11-001a, 1-11-001b, 1-11-001c, 1-11-002a, 1-11-003a, 1-11-003b, 1-11-004a, 1-11- 004b, 1-11-004c, 1-11-005a, 1-11-005b, 1-11-006a, 1-11-006b, 1-11-007a, 1-11-007b, 1-11- 007c, 1-11-008a, 1-11-008b, 1-11-009a, 1-11-009b, 1-12-001a, 1-12-002a, 1-12-003a, 1-12-004a, 1-12-005a, 1-12-006a, 1-12-007a, 1-12-008a, 1-12-009a, 1-12-010a, 1-12-011a, 1-12-012a, 1- 13-001a, 1-14-001a, 1-14-002a, 1-15-002a, 1-15-003a, 1-15-004a, 1-15-005a, 1-15-006a, 1-15- 007a, 1-16-001a, 1-16-001b, 2-1-001a, 2-1-001b, 2-1-002a, 2-1-003a, 2-1-004a, 3-1-001a, 3-1-001b, 3-1-001c, 3-1-002a, 3-1-002b, 3-1-002c
Test Example 3: Insecticidal test against Spodoptera litura A 10% emulsion of the compound of the present invention (a 10% wettable powder was used depending on the compound) was diluted with water containing a spreading agent to prepare a 500 ppm concentration drug solution. A leaf of kanran was immersed in the chemical solution for about 10 seconds. After the dipping operation was completed, the chemical solution-treated kanran leaf was air-dried and then placed in a petri dish. Five third-instar larvae of Spodoptera litura were released in each dish, and the lids were placed and stored in a thermostatic chamber at 25°C. Six days after the housing, the number of dead larvae of Spodoptera litura in a petri dish was examined, and the mortality rate was calculated from the same formula as in Test Example 1. The test was carried out in a double loop.

As a result, among the tested compounds, the following compounds showed a mortality of 90% or more.
Inventive compound: 1-1-001a, 1-1-001b, 1-1-001c, 1-1-002a, 1-1-002b, 1-1-003a, 1-1-004a, 1-1- 005a, 1-1-005c, 1-1-006a, 1-1-007a, 1-1-009a, 1-1-011a, 1-1-012a, 1-1-013a, 1-1-013b, 1-1-013c, 1-1-014a, 1-1-014c, 1-1-015a, 1-1-015b, 1-1-016a, 1-1-016b, 1-1-016c, 1- 1-017a, 1-1-018a, 1-1-019a, 1-1-020a, 1-1-020b, 1-1-023a, 1-1-023b, 1-1-023c, 1-1- 024a, 1-1-026a, 1-1-027a, 1-1-027b, 1-1-029a, 1-1-030a, 1-1-030b, 1-1-030c, 1-1-032a, 1-1-033a, 1-1-034a, 1-1-036a, 1-1-037a, 1-1-038a, 1-1-039a, 1-1-040a, 1-1-040c, 1- 1-041a, 1-1-042a, 1-1-043a, 1-1-044a, 1-1-045a, 1-1-045b, 1-1-046a, 1-1-047a, 1-1- 048a, 1-1-049a, 1-1-049b, 1-1-050a, 1-1-051a, 1-1-051b, 1-1-052a, 1-1-053a, 1-1-056a, 1-1-057a, 1-1-057c, 1-1-058a, 1-1-059a, 1-1-060a, 1-1-061a, 1-1-062a, 1-1-063a, 1- 1-064a, 1-1-065a, 1-1-066a, 1-1-067a, 1-1-068a, 1-1-069a, 1-1-070a, 1-1-070b, 1-1- 071a, 1-1-072a, 1-1-072b, 1-1-072c, 1-1-074a, 1-1-076a, 1-1-077a, 1-1-077b, 1-1-080a, 1-1-081a, 1-1-082a, 1-1-083a, 1-1-084a, 1-1-085a, 1-1-087a, 1-1-089a, 1-1-090a, 1- 1-091a, 1-1-092a, 1-1-093a, 1-1-093b, 1-1-094a, 1-1-094b, 1-1-094c, 1-1-095a, 1-1- 096a, 1-1-097a, 1-1-099a, 1-1 -100a, 1-1-101a, 1-1-103a, 1-1-103b, 1-1-104a, 1-1-105a, 1-1-105b, 1-1-106a, 1-1-109a , 1-1-110a, 1-1-110c, 1-1-111a, 1-1-112a, 1-1-113a, 1-1-114a, 1-1-114b, 1-1-115a, 1 -1-115b, 1-1-118a, 1-1-122a, 1-1-123a, 1-1-124a, 1-1-124b, 1-1-125a, 1-1-126a, 1-1 -127a, 1-1-128a, 1-1-129a, 1-1-130a, 1-1-131a, 1-1-132a, 1-1-133a, 1-1-134a, 1-1-135a , 1-1-135b, 1-1-136a, 1-1-137a, 1-1-138a, 1-1-139a, 1-1-139b, 1-1-140a, 1-1-141a, 1 -1-142a, 1-1-142b, 1-1-143a, 1-1-144a, 1-1-145a, 1-1-145b, 1-1-146a, 1-1-147a, 1-1 -148a, 1-1-149a, 1-1-150a, 1-1-151a, 1-1-152a, 1-1-153a, 1-1-153b, 1-1-154a, 1-1-155a , 1-1-156a, 1-1-157a, 1-1-158a, 1-1-159a, 1-1-160a, 1-1-161a, 1-1-162a, 1-1-163a, 1 -1-164a, 1-1-165a, 1-1-166a, 1-1-167a, 1-1-168a, 1-1-169a, 1-1-170a, 1-1-171a, 1-1 -171b, 1-1-172a, 1-1-173a, 1-1-174a, 1-1-175a, 1-1-176a, 1-1-177a, 1-1-178a, 1-1-179a , 1-1-180a, 1-1-181a, 1-1-182a, 1-1-183a, 1-1-183b, 1-1-185a, 1-1-186a, 1-1-187a, 1 -1-188a, 1-1-189a, 1-1-190a, 1-1-191a, 1-1-192a, 1-1-193a, 1-1-194a, 1-1-195a, 1-1 -196a, 1-1-197a, 1-1-198a, 1-2-001a, 1-2-002a, 1-2-004a, 1-2-004b, 1-2-004c, 1-2-005a , 1-2-006a, 1-3-001a, 1-3 002a, 1-3-003a, 1-3-004a, 1-3-005a, 1-3-006a, 1-3-007a, 1-3-008a, 1-3-009a, 1-3-010a, 1-3-011a, 1-3-012a, 1-3-013a, 1-3-014a, 1-3-015a, 1-4-001a, 1-4-002a, 1-4-003a, 1- 4-003b, 1-4-004a, 1-5-001a, 1-5-002a, 1-5-003a, 1-5-004a, 1-6-001a, 1-6-002a, 1-7- 001a, 1-8-002a, 1-8-002b, 1-8-003a, 1-8-003b, 1-8-005a, 1-8-005b, 1-8-006a, 1-8-006b, 1-8-007a, 1-8-008a, 1-8-009a, 1-8-010a, 1-8-011a, 1-8-013a, 1-8-013b, 1-8-014a, 1- 8-015a, 1-8-016a, 1-9-002a, 1-9-002b, 1-9-003a, 1-10-001a, 1-10-001b, 1-10-001c, 1-10- 002a, 1-10-002b, 1-10-002c, 1-10-003a, 1-10-004a, 1-10-005a, 1-10-006a, 1-11-001a, 1-11-001b, 1-11-001c, 1-11-002a, 1-11-003a, 1-11-004a, 1-11-004b, 1-11-004c, 1-11-005a, 1-11-005b, 1- 11-006a, 1-11-007a, 1-11-007b, 1-11-007c, 1-11-008a, 1-11-008b, 1-11-009a, 1-11-009b, 1-12- 001a, 1-12-002a, 1-12-003a, 1-12-004a, 1-12-005a, 1-12-006a, 1-12-007a, 1-12-008a, 1-12-009a, 1-12-010a, 1-12-011a, 1-12-012a, 1-13-001a, 1-14-001a, 1-14-002a, 1-15-003a, 1-15-004a, 1- 15-005a, 1-15-006a, 1-15-007a, 1-16-001a, 2-1-001a, 2-1-001b, 2-1-003a, 2-1-004a, 3-1- 001a, 3-1-001c, 3-1-002a, 3-1-002b, 3-1-002c
Test Example 4: Insecticidal activity against Thrips palmi thrips A wet filter paper was laid on a styrene cup having an inner diameter of 7 cm, and 3 cm square cut kidney bean leaves were placed thereon, and 20 larvae of Frankliniella occidentalis were placed per leaf. I inoculated my head. A 10% emulsion of the compound of the present invention (a 10% wettable powder was used depending on the compound) was diluted with water containing a spreading agent to prepare a drug solution having a concentration of 500 ppm. The prepared drug solution was sprayed at 2.5 ml per styrene cup using a rotary spray tower (2.5 mg/cm ² ).

The number of dead insects of Thrips palmi L. ingested 2 days later and the feeding damage of green beans were investigated. The mortality was calculated from the same formula as in Test Example 1.

The degree of feeding damage was determined as follows. 1 to 20% feeding damage, 2:20 to 50% feeding damage, 3:50 to 70% feeding damage, and 4:70% or more feeding damage. The test was carried out in a double loop.

As a result, among the tested compounds, the following compounds showed mortality of 50% or more and feeding damage of 2 or more.
Compounds of the present invention: 1-1-001a, 1-1-002b, 1-1-003a, 1-1-005a, 1-1-006a, 1-1-023c, 1-1-035a, 1-1- 036a, 1-1-038a, 1-1-039a, 1-1-042a, 1-1-043a, 1-1-049a, 1-1-050a, 1-1-051a, 1-1-052a, 1-1-052b, 1-1-053a, 1-1-054b, 1-1-055b, 1-1-056a, 1-1-057a, 1-1-057c, 1-1-061a, 1- 1-062a, 1-1-063a, 1-1-064a, 1-1-067a, 1-1-068a, 1-1-069b, 1-1-070a, 1-1-071a, 1-1- 072a, 1-1-074a, 1-1-076a, 1-1-080a, 1-1-081a, 1-1-082a, 1-1-087a, 1-1-089a, 1-1-090a, 1-1-093a, 1-1-095a, 1-1-096a, 1-1-097a, 1-1-099a, 1-1-105a, 1-1-106b, 1-1-109a, 1- 1-110a, 1-1-112a, 1-1-114a, 1-1-115a, 1-1-117a, 1-1-120c, 1-1-122a, 1-1-123a, 1-1- 125a, 1-1-126a, 1-1-127a, 1-1-128a, 1-1-129a, 1-1-133a, 1-1-133a, 1-1-134a, 1-1-135a, 1-1-136a, 1-1-137a, 1-1-139a, 1-1-154a, 1-1-155a, 1-1-159a, 1-1-159b, 1-1-160a, 1- 1-161a, 1-1-165a, 1-1-166a, 1-1-171a, 1-1-172a, 1-1-173a, 1-1-175a, 1-1-180a, 1-1- 190a, 1-1-191a, 1-1-194a, 1-1-195a, 1-1-196a, 1-1-198a, 1-2-006a, 1-3-012a, 1-4-003a, 1-4-004a, 1-8-007a, 1-8-008a, 1-8-011a, 1-8-013a, 1-8-014a, 1-8-015a, 1-8-016a, 1- 9-002a, 1-9-003a, 1-10-003a, 1-11-003a, 1-11-004a, 1-11-006a, 1-11-007a, 1-11-007c, 1-11- 009b, 1-12-009a, 2-1- 002a, 3-1-001a, 3-1-001b, 3-1-001c, 3-1-002a
Test Example 5: Insecticidal test against green peach aphid Wet absorbent cotton is laid on a glass petri dish having an inner diameter of 3 cm, and citrus leaves cut to the same diameter are placed thereon, and 4 wingless adults of Myzus persicae are released. I insected One day later, a 10% emulsion of the compound of the present invention (10% wettable powder depending on the compound was tested) was diluted with water containing a spreading agent to prepare a drug solution having a concentration of 500 ppm. The prepared drug solution was sprayed (2.5 mg/cm ² ) in a rotary spraying tower, covered with a lid, and housed in a thermostatic chamber at 25°C. Six days after storage, the number of dead peach aphids in the petri dish was examined, and the mortality rate was calculated from the same formula as in Test Example 1. The test was carried out in a double loop.

As a result, among the tested compounds, the following compounds showed a mortality of 90% or more.
The compound of the present invention: 1-1-001a, 1-1-002a, 1-1-002b, 1-1-003a, 1-1-004a, 1-1-004b, 1-1-004c, 1-1- 005a, 1-1-006a, 1-1-007a, 1-1-009a, 1-1-011a, 1-1-012a, 1-1-012b, 1-1-013a, 1-1-013c, 1-1-014a, 1-1-014c, 1-1-015a, 1-1-015b, 1-1-016c, 1-1-017a, 1-1-018a, 1-1-019a, 1- 1-020a, 1-1-023a, 1-1-024a, 1-1-025c, 1-1-026a, 1-1-027a, 1-1-032a, 1-1-033a, 1-1- 034a, 1-1-035a, 1-1-036a, 1-1-037a, 1-1-038a, 1-1-039a, 1-1-040b, 1-1-040c, 1-1-041a, 1-1-042a, 1-1-043a, 1-1-044a, 1-1-045b, 1-1-046a, 1-1-047a, 1-1-048a, 1-1-049a, 1- 1-049b, 1-1-050a, 1-1-051a, 1-1-052a, 1-1-053a, 1-1-056a, 1-1-057a, 1-1-057c, 1-1- 058a, 1-1-059a, 1-1-060a, 1-1-061a, 1-1-062a, 1-1-063a, 1-1-064a, 1-1-065a, 1-1-066a, 1-1-067a, 1-1-068a, 1-1-071a, 1-1-072a, 1-1-073b, 1-1-074a, 1-1-077a, 1-1-077b, 1- 1-080a, 1-1-082a, 1-1-086a, 1-1-087a, 1-1-090a, 1-1-091a, 1-1-093a, 1-1-093b, 1-1- 095a, 1-1-096a, 1-1-097a, 1-1-099a, 1-1-100a, 1-1-101a, 1-1-102a, 1-1-105a, 1-1-106a, 1-1-106b, 1-1-106c, 1-1-107a, 1-1-108a, 1-1-109a, 1-1-110a, 1-1-112a, 1-1-113a, 1- 1-115a, 1-1-116a, 1-1-117a, 1-1-118a, 1-1-120c, 1-1-121a, 1-1-122a, 1-1-123a, 1-1- 125a, 1-1-128a, 1-1-129a, 1-1 -130a, 1-1-131a, 1-1-132a, 1-1-133a, 1-1-135a, 1-1-136a, 1-1-137a, 1-1-138a, 1-1-139a , 1-1-140a, 1-1-142a, 1-1-143a, 1-1-146a, 1-1-149a, 1-1-154a, 1-1-155a, 1-1-156a, 1 -1-158a, 1-1-159a, 1-1-160a, 1-1-161a, 1-1-163a, 1-1-165a, 1-1-166a, 1-1-168a, 1-1 -169a, 1-1-170a, 1-1-171a, 1-1-172a, 1-1-173a, 1-1-175a, 1-1-180a, 1-1-181a, 1-1-183a , 1-1-185a, 1-1-187a, 1-1-188a, 1-1-189a, 1-1-190a, 1-1-191a, 1-1-192a, 1-1-193a, 1 -1-194a, 1-1-195a, 1-1-196a, 1-1-197a, 1-1-198a, 1-1-199a, 1-2-001a, 1-2-002a, 1-3 -001a, 1-3-002a, 1-3-003a, 1-3-004a, 1-3-005a, 1-3-006a, 1-3-007a, 1-3-009a, 1-3-010a , 1-3-011a, 1-3-012a, 1-4-001a, 1-4-002a, 1-4-003a, 1-4-004a, 1-5-001a, 1-5-002a, 1 -5-003a, 1-5-004a, 1-6-001a, 1-6-002a, 1-8-002a, 1-8-002b, 1-8-003a, 1-8-003b, 1-8 -004b, 1-8-005a, 1-8-006a, 1-8-008a, 1-8-010a, 1-8-013a, 1-8-014a, 1-8-015b, 1-8-016a , 1-9-002a, 1-9-003a, 1-10-001a, 1-10-001b, 1-10-002a, 1-10-002b, 1-10-002c, 1-10-003a, 1 -10-004a, 1-11-001a, 1-11-001b, 1-11-002a, 1-11-003a, 1-11-004a, 1-11-007a, 1-11-007b, 1-11 -007c, 1-11-008a, 1-11-009a, 1-12-001a, 1-12-002a, 1-12-003a, 1-12-004a, 1-12-005a, 1-12-006 a, 1-12-007a, 1-12-008a, 1-14-001a, 1-14-002a, 1-15-003a, 1-15-004a, 1-15-007a, 1-16-001a, 1-17-001a,2-1-001a,2-1-002a,2-1-003a,2-1-004a,3-1-001a,3-1-001c,3-1-002a
Test Example 6 Insecticidal test against silver leaf whitefly White bean leaves cut into 3 cm pieces were placed on a styrene cup having an inner diameter of 7 cm, which was covered with moist filter paper. A 10% emulsion of the compound of the present invention (10% wettable powder was used depending on the compound) was diluted with water containing a spreading agent to prepare a drug solution having a concentration of 500 ppm. The drug solution was sprayed at 2.5 ml per styrene cup (2.5 mg/cm ² ). After air-drying the leaves, adults of silver leaf whitefly (Bemisia argentifoliai) were released, and the leaves were capped and stored in a thermostatic chamber at 25°C. The number of dead insects after 5 days was investigated, and the death rate was calculated from the same formula as in Test Example 1. The test was carried out in a double loop.

As a result, among the tested compounds, the following compounds showed a mortality of 90% or more.
The compound of the present invention: 1-1-035a, 1-1-036a, 1-1-043a, 1-1-049a, 1-1-047a, 1-1-094a, 1-1-095a, 1-1- 096a, 1-1-099a, 1-1-125a, 1-3-001a, 1-14-001a, 3-1-002a
Test Example 7: Soil irrigation treatment test for green peach aphid A 10% emulsion of the compound of the present invention was diluted with tap water to prepare a drug solution having a concentration of 500 ppm.

10 ml of the above drug solution was irrigated into the soil portion of the root of the cabbage seedling (2.5 true leaf stage) planted in a plastic cup. After the irrigation treatment, the cabbage seedlings were left in the greenhouse. One day after the irrigation treatment, 20 adult/green aphids (Myzus persicae) were released. After the insect treatment, the cabbage seedlings were left in the greenhouse. Six days after the insects were released, the number of living green peach aphids was examined, and a control value was calculated from the following formula.

Control value (%)={1-(Cb*Tai)/(Cai*Tb)}*100
The letters in the formula represent the following.
Cb: Number of insects before treatment in untreated plot Cai: Number of surviving insects in untreated plot Tb: Number of insects before treatment in treated plot Tai: Number of surviving insects in final survey in treated plot Among the tested compounds, the following compounds showed a control value of 90% or more.
The compound of the present invention: 1-1-001a, 1-1-002a, 1-1-003a, 1-1-004a, 1-1-005a, 1-1-006a, 1-1-012a, 1-1- 013a, 1-1-014a, 1-1-016a, 1-1-017a, 1-1-018a, 1-1-029a, 1-1-032a, 1-1-035a, 1-1-039a, 1-1-042a, 1-1-043a, 1-1-049a, 1-1-057a, 1-1-058a, 1-1-060a, 1-1-074a, 1-1-093a, 1- 1-097a, 1-1-106a, 1-1-112a, 1-1-113a, 1-1-122a, 1-1-125a, 1-1-154a, 1-1-160a, 1-1- 170a, 1-1-173a, 1-8-002a, 1-8-003a, 1-8-005a, 1-8-006a, 1-8-010a, 1-8-013a, 1-9-002a, 1-12-008a, 1-14-001a, 1-16-001a, 2-1-002a
Test Example 8: Osmotic migration test for brown planthopper A 10% emulsion of the compound of the present invention was diluted with tap water to prepare a drug solution having a concentration of 20 ppm, and the roots of rice cell seedlings (two-leaf stage) were dipped. After 7 days, rice was cut out and placed in a test tube, and 5 third-instar larvae of the brown planthopper (Nilaparva lugens) were released in each test tube, covered with a sponge, and stored in a constant temperature room at 25°C. Six days after releasing the insects, the number of dead planthoppers was examined, and the mortality rate (%) (the number of dead insects/the number of test insects×100) was calculated. The test was carried out in a double loop.

As a result, among the tested compounds, the following compounds showed a mortality of 90% or more.
Inventive compound: 1-1-001a, 1-1-001b, 1-1-002a, 1-1-005a, 1-1-006a, 1-1-013a, 1-1-014a, 1-1- 017a, 1-1-018a, 1-1-020a, 1-1-030a, 1-1-032a, 1-1-035a, 1-1-036a, 1-1-038a, 1-1-039a, 1-1-042a, 1-1-043a, 1-1-044a, 1-1-049a, 1-1-052a, 1-1-057a, 1-1-057c, 1-1-058a, 1- 1-067a, 1-1-070a, 1-1-072a, 1-1-074a, 1-1-076a, 1-1-077a, 1-1-092a, 1-1-093a, 1-1- 095a, 1-1-096a, 1-1-097a, 1-1-099a, 1-1-105a, 1-1-106a, 1-1-107a, 1-1-109a, 1-1-111a, 1-1-113a, 1-1-117a, 1-1-122a, 1-1-125a, 1-1-131a, 1-1-133a, 1-1-136a, 1-1-138a, 1- 1-145b, 1-1-154a, 1-1-157a, 1-1-160a, 1-1-165a, 1-1-166a, 1-1-168a, 1-1-170a, 1-1- 173a, 1-1-180a, 1-1-182a, 1-1-183a, 1-1-185a, 1-1-189a, 1-1-190a, 1-1-191a, 1-1-192a, 1-1-193a, 1-1-194a, 1-1-195a, 1-1-196a, 1-1-197a, 1-1-198a, 1-2-002a, 1-3-001a, 1- 3-005a, 1-3-007a, 1-3-015a, 1-8-002a, 1-8-005a, 1-8-006a, 1-8-008a, 1-8-010a, 1-8- 013a, 1-8-016a, 1-9-002a, 1-11-001a, 1-11-002a, 1-11-003a, 1-11-004a, 1-11-007a, 1-11-009a, 1-12-006a, 1-12-008a, 1-12-009a, 1-14-001a, 1-14-002a, 1-16-001a, 2-1-002a, 3-1-002b
Test Example 9: Soil irrigation treatment test against diamondback moth A 10% emulsion of the compound of the present invention was diluted with tap water to prepare a drug solution having a concentration of 500 ppm.

10 ml of the above drug solution was irrigated into the soil portion of the root of the cabbage seedling (2.5 true leaf stage) planted in a plastic cup. After the irrigation treatment, the cabbage seedlings were left in the greenhouse. Five days after the irrigation treatment, the leaves of kanran were cut out and placed in a petri dish. Five third-instar larvae of diamondback moth (Plutella xylostella) were released in each dish, covered with a lid, and stored in a thermostatic chamber at 25°C. Six days after storage, the number of dead larvae of diamondback moth in the petri dish was examined, and the mortality rate was calculated from the same formula as in Test Example 1. The test was carried out in a double loop.

As a result, among the tested compounds, the following compounds showed a control value of 90% or more.
Inventive compound: 1-1-001a, 1-1-001c, 1-1-002a, 1-1-003a, 1-1-004a, 1-1-005a, 1-1-006a, 1-1- 013a, 1-1-014a, 1-1-015a, 1-1-016a, 1-1-018a, 1-1-029a, 1-1-030a, 1-1-039a, 1-1-042a, 1-1-043a, 1-1-049a, 1-1-050a, 1-1-052a, 1-1-056a, 1-1-057a, 1-1-058a, 1-1-059a, 1- 1-060a, 1-1-063a, 1-1-069a, 1-1-070a, 1-1-074a, 1-1-076a, 1-1-077a, 1-1-080a, 1-1- 082a, 1-1-090a, 1-1-093a, 1-1-096a, 1-1-097a, 1-1-099a, 1-1-103a, 1-1-103b, 1-1-105a, 1-1-106a, 1-1-107a, 1-1-109a, 1-1-111a, 1-1-112a, 1-1-113a, 1-1-117a, 1-1-122a, 1- 1-125a, 1-1-126a, 1-1-127a, 1-1-128a, 1-1-129a, 1-1-132a, 1-1-133a, 1-1-135a, 1-1- 136a, 1-1-140a, 1-1-143a, 1-1-146a, 1-1-154a, 1-1-157a, 1-1-160a, 1-1-165a, 1-1-166a, 1-1-170a, 1-1-172a, 1-1-173a, 1-1-182a, 1-3-001a, 1-3-004a, 1-3-013a, 1-3-014a, 1- 4-001a, 1-4-004a, 1-8-002a, 1-8-003a, 1-8-005a, 1-8-006a, 1-8-007a, 1-8-008a, 1-8- 010a, 1-8-013a, 1-8-016a, 1-9-002a, 1-10-002a, 1-11-001a, 1-11-002a, 1-11-003a, 1-11-004a, 1-11-007a, 1-11-008a, 1-11-009a, 1-12-008a, 1-12-009a, 1-12-011a, 1-14-001a, 1-14-002a, 1- 15-005a, 1-16-001a, 2-1-002a
Test Example 10: Effect test on soybean aphid in seed treatment 2.4 mg of the compound of the present invention was diluted with 97.6 μl of acetone. Four soybean seeds were placed in a plastic tube having a total volume of 50 ml, and the above dilution solution was poured into the tube, and the acetone was completely evaporated while stirring so that the compound was uniformly attached to the seeds. The treated seeds were planted at 4 seeds/pot and left in a greenhouse. After development of the primary leaves, two adult soybean aphids (Aphis glycines) were released. The number of surviving insects 7 days after the release was investigated, and a control value was calculated from the following formula.

Control value (%)={1-(Cb*Tai)/(Cai*Tb)}*100
The letters in the formula represent the following.
Cb: Number of insects before treatment in untreated plot Cai: Number of surviving insects in untreated plot Tb: Number of insects before treatment in treated plot Tai: Number of surviving insects in final survey in treated plot Among the tested compounds, the following compounds showed a control value of 90% or more.
The compound of the present invention: 1-1-001a, 1-1-002a, 1-1-003a, 1-1-004a, 1-1-005a, 1-1-006a, 1-1-012a, 1-1- 013a, 1-1-014a, 1-1-016a, 1-1-017a, 1-1-018a, 1-1-029a, 1-1-032a, 1-1-035a, 1-1-039a, 1-1-042a, 1-1-043a, 1-1-049a, 1-1-057a, 1-1-058a, 1-1-060a, 1-1-074a, 1-1-093a, 1- 1-097a, 1-1-106a, 1-1-112a, 1-1-113a, 1-1-122a, 1-1-125a, 1-1-126a, 1-1-154a, 1-1- 160a, 1-1-170a, 1-1-172a, 1-1-173a, 1-3-001a, 1-8-002a, 1-8-003a, 1-8-005a, 1-8-006a, 1-8-010a, 1-8-013a, 1-9-002a, 1-12-008a, 1-14-001a, 1-16-001a
Test Example 11: Effect test against Rhizopus littoralis L. By dissolving 3.5 mg of the compound of the present invention in 3.5 ml of acetone, a 1000 ppm concentration drug solution was prepared. After applying 350 μl of the chemical solution to the bottom and side surfaces of a glass container having an inner wall surface area of 35 cm ² , acetone was volatilized to form a thin film of the compound on the inner wall of the glass container. The inner wall of the glass container used was 35 cm ² , and the treatment dose was 10 μg/cm ² .

Five first nymphs (mixed male and female) of Rhipicephalus sanguineus were released in the above-treated glass container, covered with a lid, and stored in a thermostatic chamber at 25°C. Four days after the insect was released, the number of dead ticks of the ticks was examined, and the death rate was calculated from the same formula as in Test Example 1.

As a result, among the tested compounds, the following compounds showed a mortality of 50% or more.
The compound of the present invention: 1-1-001a, 1-1-001b, 1-1-002a, 1-1-003a, 1-1-003b, 1-1-003c, 1-1-004a, 1-1- 004b, 1-1-004c, 1-1-005a, 1-1-005b, 1-1-006a, 1-1-006b, 1-1-010a, 1-1-011a, 1-1-012a, 1-1-013a, 1-1-014a, 1-1-014b, 1-1-016a, 1-1-016c, 1-1-017a, 1-1-018a, 1-1-020a, 1- 1-022a, 1-1-023c, 1-1-026a, 1-1-023c, 1-1-027b, 1-1-035a, 1-1-039a, 1-1-040a, 1-1- 042a, 1-1-043a, 1-1-045a, 1-1-046a, 1-1-047a, 1-1-049a, 1-1-051a, 1-1-052b, 1-1-053a, 1-1-055a, 1-1-057a, 1-1-057c, 1-1-059b, 1-1-060a, 1-1-062a, 1-1-063a, 1-1-065a, 1- 1-067a, 1-1-068a, 1-1-071a, 1-1-072a, 1-1-072b, 1-1-075a, 1-1-080a, 1-1-083a, 1-1- 088a, 1-1-093a, 1-1-093b, 1-1-094a, 1-1-094b, 1-1-095a, 1-1-096a, 1-1-099a, 1-1-103a, 1-1-105a, 1-1-105b, 1-1-105c, 1-1-106a, 1-1-106b, 1-1-106c, 1-1-107a, 1-1-108a, 1- 1-109a, 1-1-110a, 1-1-110c, 1-1-111a, 1-1-111b, 1-1-112a, 1-1-113a, 1-1-114a, 1-1- 114b, 1-1-115a, 1-1-115b, 1-1-116a, 1-1-118b, 1-1-118c, 1-1-120c, 1-1-124a, 1-1-124b, 1-1-125a, 1-1-126a, 1-1-129a, 1-1-130a, 1-1-132a, 1-1-133a, 1-1-134a, 1-1-136a, 1- 1-137a, 1-1-138a, 1-1-139b, 1-1-140a, 1-1-142a, 1-1-143a, 1-1-144a, 1-1-145a, 1-1- 146a, 1-1-147a, 1-1-150a, 1-1 -151a, 1-1-152a, 1-1-153a, 1-1-153b, 1-1-155a, 1-1-156a, 1-1-158a, 1-1-159a, 1-1-159b , 1-1-160a, 1-1-161a, 1-1-162a, 1-1-163a, 1-1-164a, 1-1-165a, 1-1-169b, 1-1-170a, 1 -1-171a, 1-1-171b, 1-1-172a, 1-1-172b, 1-1-173b, 1-1-175a, 1-1-176a, 1-1-183a, 1-1 -190a, 1-1-196a, 1-3-004a, 1-3-005a, 1-3-011a, 1-3-013a, 1-3-014a, 1-3-015a, 1-4-004a , 1-5-001a, 1-6-001a, 1-8-002a, 1-8-005a, 1-8-006a, 1-8-006b, 1-8-008a, 1-8-010a, 1 -8-011a, 1-8-013a, 1-8-014a, 1-8-014b, 1-8-015b, 1-9-002a, 1-9-002b, 1-9-003a, 1-10 -002c, 1-10-004a, 1-10-005a, 1-11-004a, 1-11-004c, 1-11-005a, 1-11-006a, 1-11-007c, 1-11-008a , 1-11-008b, 1-12-004a, 1-12-007a, 1-12-010a, 1-12-011a, 1-12-012a, 1-14-002a, 1-15-003a, 1 -15-005a, 1-15-006a, 1-16-001a, 2-1-002a, 2-1-003a, 2-1-003b, 3-1-002a, 3-1-002b, 3-1 -002c
Test Example 12: Effect test on cat flea 3.5 mg of the compound of the present invention was dissolved in 3.5 ml of acetone to prepare a drug solution having a concentration of 1000 ppm. After applying 350 μl of the chemical solution to the bottom and side surfaces of a glass container having an inner wall surface area of 35 cm ² , acetone was volatilized to form a thin film of the compound on the inner wall of the glass container. Since the inner wall of the glass container used was 35 cm ² , the treatment dose was 10 μg/cm ² .

Into the treated glass container, 5 adult cat fleas (Ctenocephalides felis) (male and female mixed) were released, covered and placed in a constant temperature room at 25°C. Four days after the insect was released, the number of dead fleas was examined, and the mortality rate was calculated from the same formula as in Test Example 1.

As a result, among the tested compounds, the following compounds showed a mortality of 50% or more.
The compound of the present invention: 1-1-001a, 1-1-001b, 1-1-001c, 1-1-002a, 1-1-002b, 1-1-003a, 1-1-003b, 1-1- 003c, 1-1-004a, 1-1-004b, 1-1-004c, 1-1-005a, 1-1-005b, 1-1-005c, 1-1-006a, 1-1-007a, 1-1-009a, 1-1-012a, 1-1-013a, 1-1-013b, 1-1-013c, 1-1-014a, 1-1-014c, 1-1-015a, 1- 1-015b, 1-1-016a, 1-1-016b, 1-1-016c, 1-1-017a, 1-1-018a, 1-1-019a, 1-1-020a, 1-1- 023a, 1-1-023b, 1-1-023c, 1-1-024a, 1-1-025c, 1-1-026a, 1-1-027a, 1-1-027b, 1-1-029a, 1-1-030a, 1-1-032a, 1-1-033a, 1-1-034a, 1-1-035a, 1-1-036a, 1-1-037a, 1-1-039a, 1- 1-040c, 1-1-041a, 1-1-042a, 1-1-043a, 1-1-044a, 1-1-045a, 1-1-046a, 1-1-047a, 1-1- 047b, 1-1-048a, 1-1-048b, 1-1-049a, 1-1-050a, 1-1-050b, 1-1-051a, 1-1-051b, 1-1-052a, 1-1-052b, 1-1-053a, 1-1-054b, 1-1-055a, 1-1-056a, 1-1-057a, 1-1-057c, 1-1-058a, 1- 1-058b, 1-1-059b, 1-1-060a, 1-1-060b, 1-1-061a, 1-1-062a, 1-1-062b, 1-1-063a, 1-1- 063b, 1-1-064a, 1-1-065a, 1-1-066a, 1-1-066b, 1-1-067a, 1-1-067b, 1-1-068a, 1-1-069a, 1-1-070a, 1-1-071a, 1-1-072a, 1-1-072b, 1-1-072c, 1-1-073b, 1-1-074a, 1-1-074b, 1- 1-075a, 1-1-076a, 1-1-077a, 1-1-077b, 1-1-080a, 1-1-081a, 1-1-082a, 1-1-084a, 1-1- 085a, 1-1-086a, 1-1-087a, 1-1 -088a, 1-1-089a, 1-1-090a, 1-1-091a, 1-1-092a, 1-1-093a, 1-1-093b, 1-1-094a, 1-1-094b , 1-1-094c, 1-1-095a, 1-1-096a, 1-1-097a, 1-1-099a, 1-1-101a, 1-1-102a, 1-1-103a, 1 -1-103b, 1-1-104a, 1-1-105a, 1-1-105b, 1-1-105c, 1-1-106a, 1-1-106b, 1-1-106c, 1-1 -107a, 1-1-108a, 1-1-109a, 1-1-110a, 1-1-110c, 1-1-111a, 1-1-111b, 1-1-112a, 1-1-113a , 1-1-114a, 1-1-114b, 1-1-115a, 1-1-115b, 1-1-116a, 1-1-117a, 1-1-118a, 1-1-118b, 1 -1-119c, 1-1-122a, 1-1-123a, 1-1-124a, 1-1-124b, 1-1-125a, 1-1-126a, 1-1-127a, 1-1 -127b, 1-1-128a, 1-1-129a, 1-1-130a, 1-1-130b, 1-1-132a, 1-1-133a, 1-1-134a, 1-1-135a , 1-1-135b, 1-1-136a, 1-1-137a, 1-1-138a, 1-1-139a, 1-1-139b, 1-1-140a, 1-1-141a, 1 -1-142a, 1-1-142b, 1-1-143a, 1-1-144a, 1-1-145a, 1-1-145b, 1-1-146a, 1-1-147a, 1-1 -148a, 1-1-148b, 1-1-150a, 1-1-151a, 1-1-153a, 1-1-154a, 1-1-155a, 1-1-156a, 1-1-157a , 1-1-158a, 1-1-159a, 1-1-159b, 1-1-160a, 1-1-161a, 1-1-162a, 1-1-163a, 1-1-164a, 1 -1-165a, 1-1-166a, 1-1-167b, 1-1-169a, 1-1-169b, 1-1-170a, 1-1-171a, 1-1-172a, 1-1 -173b, 1-1-175a, 1-1-180a, 1-1-181a, 1-1-183a, 1-1-186a, 1-1-187a, 1-1-190a, 1-1-191a , 1-1-192a, 1-1-193a, 1-1- 194a, 1-1-196a, 1-1-197a, 1-1-198a, 1-1-199a, 1-2-001a, 1-3-001a, 1-3-002a, 1-3-003a, 1-3-004a, 1-3-005a, 1-3-006a, 1-3-007a, 1-3-008a, 1-3-009a, 1-3-010a, 1-3-011a, 1- 3-012a, 1-3-013a, 1-3-014a, 1-3-015a, 1-4-001a, 1-4-002a, 1-4-003a, 1-4-003b, 1-4- 004a, 1-5-001a, 1-5-002a, 1-5-003a, 1-5-004a, 1-8-002a, 1-8-002b, 1-8-003a, 1-8-004b, 1-8-005a, 1-8-006a, 1-8-006b, 1-8-007a, 1-8-007b, 1-8-008a, 1-8-009a, 1-8-010a, 1- 8-011a, 1-8-013a, 1-8-013c, 1-8-014a, 1-8-014b, 1-8-016a, 1-8-016b, 1-9-002a, 1-9- 002b, 1-9-003a, 1-9-003b, 1-10-001b, 1-10-002a, 1-10-002b, 1-10-002c, 1-10-003a, 1-10-004a, 1-11-001a, 1-11-001b, 1-11-001c, 1-11-003a, 1-11-004a, 1-11-004c, 1-11-005b, 1-11-006a, 1- 11-007b, 1-11-007c, 1-11-008a, 1-11-008b, 1-11-009a, 1-11-009b, 1-12-001a, 1-12-002a, 1-12- 003a, 1-12-006a, 1-12-007a, 1-12-008a, 1-12-009a, 1-12-010a, 1-12-011a, 1-12-012a, 1-14-001a, 1-14-002a, 1-15-003a, 1-15-004a, 1-15-005a, 1-15-006a, 1-15-007a, 1-16-001a, 1-16-001b, 1- 17-001a,2-1-001a,2-1-002a,2-1-003a,2-1-003b,3-1-001a,3-1-001b,3-1-001c,3-1- 002a, 3-1-002b, 3-1-002c
Test Example 13: Oral administration test of Pseudococcus communis parasitism by oral administration to rats 5 mg of the compound of the present invention was dissolved in 5 ml of olive oil to prepare a drug solution for administration. The drug solution was orally administered in an amount of 10 ml per kg of rat body weight using a stomach tube. The oral administration was performed twice per group. One hour after administration of the drug solution, 50 first nymphs (mixed sex) of Rhipicephalus sanguineus were released per rat. Three days after the release of the insects, the number of parasites of the test mites was examined, and the control rate was calculated by the following formula.

Control rate (%)=100×(1-number of parasitic ticks in administration group/number of parasitic ticks in non-administration group).
As a result, among the tested compounds, the following compounds showed a control rate of 70% or more.
The compound of the present invention: 1-1-001a, 1-1-002a, 1-1-003a, 1-1-006a, 1-1-015a, 1-1-016a, 1-1-096a, 1-1- 171a, 1-1-103a, 1-3-011a, 1-9-002a, 1-12-010a, 1-12-007a
Test Example 14: Insecticidal test against housefly 2 mg of the compound of the present invention was dissolved in 1 ml of acetone to prepare a drug solution having a concentration of 2 μg/μl. After adult female housefly (Musca domestica) females were allowed to sleep in carbon dioxide, 1 μl of the prepared drug solution was applied to the back of the pest of the pest using a topical application device (manufactured by Burkard Scientific). After the chemical treatment, the treated pests were transferred to a plastic cup with a lid having an inner diameter of 7.5 cm and a height of 4 cm, and stored in a thermostatic chamber at 25°C. The number of dead insects was examined 3 days after the treatment, and the dead insect rate was calculated from the same formula as in Test Example 1. The test was repeated with 5 animals in duplicate.

As a result, the following compounds showed a mortality of 70% or more.
The compound of the present invention: 1-1-001a, 1-1-002a, 1-1-003a, 1-1-013a, 1-1-015a, 1-1-016a, 1-1-051a, 1-1- 067a, 1-1-070a, 1-1-103a, 1-1-122a, 1-8-005a, 1-12-007a
Test Example 15: Insecticidal test against German cockroaches 2 mg of the compound of the present invention was dissolved in 0.2 ml of acetone to prepare a drug solution having a concentration of 10 μg/μl. After adult male adult cockroach (Blattela germanica) was put to sleep in carbon dioxide, the prepared chemical solution was applied to the abdomen of the pest by using a local application device (manufactured by Burkard Scientific) at 1 μl per head. After the chemical treatment, it was transferred to a waist-high dish having an inner diameter of 6 cm and a height of 6 cm and stored in a constant temperature chamber at 25°C. The number of agony insects and the number of dead insects were examined 3 days after the treatment, and the anguished death rate was calculated from the following formula. The test was repeated with 5 animals and 4 times.

Agony dead insect rate (%) = (number of agony insects + number of dead insects) / number of test insects x 100
As a result, the following compounds showed a mortality rate of agony of 70% or more.
Inventive compound: 1-1-001a, 1-1-002a, 1-1-003a, 1-1-013a, 1-1-015a, 1-1-016a, 1-1-067a, 1-1- 070a, 1-1-103a, 1-1-122a, 1-8-005a, 1-11-007a, 1-12-007a
Test Example 16: Insecticidal test against Yamato termite A 10% emulsion of the compound of the present invention was prepared. The emulsion was diluted with water to prepare a 100 ppm concentration drug solution. 0.5 ml of the chemical solution was added dropwise to 10 g of river sand, and the river sand and the chemical solution were mixed. 1% agar (2 cm square) was laid on a petri dish having an inner diameter of 4 cm, and the above-mentioned chemical-treated river sand and a filter paper piece as a bait were put therein. The termites (Reticulitermes speratus) were released here and then stored in a thermostatic chamber at 25°C. The number of dead insects was investigated 10 days after the treatment, and the dead insect rate was calculated from the same formula as in Test Example 1. The test was repeated twice.

As a result, the following compounds showed a mortality of 70% or more.
The compound of the present invention: 1-1-001a, 1-1-002a, 1-1-003a, 1-1-013a, 1-1-015a, 1-1-016a, 1-1-051a, 1-1- 067a, 1-1-070a, 1-1-103a, 1-1-122a, 1-8-005a, 1-11-007a, 1-12-007a
Test Example 17: Insecticidal test against Culex pipiens 2 mg of the compound of the present invention was dissolved in 0.2 ml of dimethyl sulfoxide to prepare a 1% (w/v) dimethyl sulfoxide solution. The solution was diluted 100 times with distilled water to prepare a drug solution having a compound concentration of 100 ppm. As the test container, a 1.9 ml plastic container (Cellstar 24 well plate, manufactured by GREINER) was used. To this, 0.7 ml of water containing 10 to 30 larvae of Culex pipiens molestus after 1 day of hatching, and 0.2 ml of an aqueous solution in which a feed for ornamental fish (Tetramin, manufactured by Tetra Japan) is suspended as bait are added. It was 0.1 ml of the above-prepared chemical solution was added here and stored in a constant temperature room at 25°C. The number of dead insects was investigated one day after the treatment, and the dead insect rate was calculated from the same formula as in Test Example 1. The test was repeated twice.

As a result, the following compounds showed 100% mortality.
The compound of the present invention: 1-1-001a, 1-1-002a, 1-1-003a, 1-1-013a, 1-1-015a, 1-1-016a, 1-1-051a, 1-1- 067a, 1-1-070a, 1-1-103a, 1-1-122a, 1-8-005a, 1-11-007a, 1-12-007a
Test Example 18: Insecticidal test against Aedes albopictus larvae 2 mg of the compound of the present invention was dissolved in 0.2 ml of dimethyl sulfoxide to prepare a 1% (w/v) dimethyl sulfoxide solution. 0.01 ml of the solution was added to 0.99 ml of pure water to prepare a 0.01% (w/v) chemical solution. A 0.3 ml plastic container (Cellstar 96 well cell culture plate, manufactured by GREINER) was used as a test container. 0.09 ml of distilled water containing 30 larvae of Aedes albopictus one day after hatching was placed in the test container, and 0.01 ml of a chemical solution was added dropwise to a final concentration of 10 ppm. The test container was capped and stored in a thermostatic chamber at 25°C. The number of dead insects was examined 3 days after the treatment, and the dead insect rate was calculated from the same formula as in Test Example 1.

As a result, the following compounds showed a mortality of 70% or more.
The compound of the present invention: 1-1-001a, 1-1-002a, 1-1-003a, 1-1-004a, 1-1-005a, 1-1-006a, 1-1-012a, 1-1- 013a, 1-1-014a, 1-1-015a, 1-1-016a, 1-1-017a, 1-1-018a, 1-1-020a, 1-1-023c, 1-1-042a, 1-1-043a, 1-1-044a, 1-1-046a, 1-1-049a, 1-1-051a, 1-1-053a, 1-1-055a, 1-1-057a, 1- 1-060a, 1-1-062a, 1-1-067a, 1-1-068a, 1-1-070a, 1-1-071a, 1-1-072a, 1-1-093a, 1-1- 094a, 1-1-095a, 1-1-096a, 1-1-099a, 1-1-103a, 1-1-105a, 1-1-106a, 1-1-109a, 1-1-110a, 1-1-111a, 1-1-112a, 1-1-113a, 1-1-115a, 1-1-116a, 1-1-118a, 1-1-122a, 1-1-123a, 1- 1-124b, 1-1-125a, 1-1-126a, 1-1-140a, 1-1-143a, 1-1-146a, 1-1-160a, 1-1-165a, 1-1- 171a, 1-1-172a, 1-1-175a, 1-1-183a, 1-1-190a, 1-1-196a, 1-1-197a, 1-3-004a, 1-3-005a, 1-3-011a, 1-3-014a, 1-3-015a, 1-4-004a, 1-5-001a, 1-8-005a, 1-8-006a, 1-8-008a, 1- 8-010a, 1-8-013a, 1-8-014a, 1-9-002a, 1-10-005a, 1-10-006a, 1-11-004a, 1-11-006a, 1-11- 007a, 1-12-007a, 1-12-009a, 1-12-010a, 1-12-011a, 1-12-012a, 1-14-002a, 1-15-003a, 1-15-005a, 1-15-006a, 2-1-002a, 2-1-003a, 3-1-002a

The compound of the present invention is a very useful compound which exhibits excellent pest control activity and has almost no adverse effect on non-target organisms such as mammals, fish and beneficial insects.

Claims (25)

Formula (1):

[In the formula, D substituted with -S(O) _n R ¹ represents a ring represented by any one of D 1, D 2 and D 3,

Q represents a ring represented by any of Q1, Q2, Q3 or Q4,

G ₁ represents a nitrogen atom or C(Y1),
G ₂ represents a nitrogen atom or C(Y2),
G ₃ represents a nitrogen atom or C(Y3),
G ₄ represents a nitrogen atom or C(Y4),
G ₅ represents a nitrogen atom or C(Y5),
T ₁ represents N(T _1a ), an oxygen atom or a sulfur atom,
A ¹ represents N(A ^1a ), an oxygen atom or a sulfur atom,
A ² represents a nitrogen atom or C(R ² ),
A ³ represents a nitrogen atom or C(R ³ ),
A ⁴ represents a nitrogen atom or C(R ⁴ ),
A ⁵ represents a nitrogen atom or C(R ⁵ ),
A ⁸ represents a nitrogen atom or C(R ⁸ ),
R ¹ is C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, (C ₁ -C ₆ )alkyl optionally substituted with R ^1a , C ₂ -C ₆ alkenyl, C ₂ -C ₆ haloalkenyl, C ₂ -C _{6 alkynyl,} C 2 -C _{6 haloalkynyl,} C 3 -C _{6 cycloalkyl,} C 3 -C _{6 halocycloalkyl,} C 3 -C ₆ cycloalkyl _(C 1 -C ₆₎ alkyl, _{C 3} Represents a -C ₆ halocycloalkyl(C ₁ -C ₆ )alkyl or hydroxy(C ₁ -C ₆ )alkyl,
R ^1a represents C ₁ -C ₈ alkoxy, C ₁ -C ₈ haloalkoxy, C ₁ -C ₈ alkoxycarbonyl, C ₁ -C ₆ alkylthio, C ₁ -C ₆ haloalkylthio, C ₁ -C ₆ alkylsulfinyl, Represents C ₁ -C ₆ haloalkylsulfinyl, C ₁ -C ₆ alkylsulfonyl, C ₁ -C ₆ haloalkylsulfonyl or cyano,
R ² is a hydrogen atom, a halogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₈ alkoxy, C ₁ -C ₈ haloalkoxy, C ₃ -C ₆ cycloalkyl, C ₃ -. C _{6 halocycloalkyl,} C 1 -C _{6 alkylthio,} C 1 -C _{6 haloalkylthio,} C 1 -C _{6 alkylsulfinyl,} C 1 -C _{6 haloalkylsulfinyl,} C 1 -C _{6 alkylsulfonyl,} C 1 -C ₆ It represents ^{haloalkylsulfonyl, -C (O) R 20a,} -C (O) OH, ^{_{hydroxy, -NH 2, -NHR 20g, -N}} (R 20h) R 20g, mercapto, cyano or nitro,
R ³ is a hydrogen atom, a halogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₂ -C ₆ haloalkenyl, C ₂ -C ₆ haloalkynyl, C ₁ -C ₈ alkoxy, C ₁ -. C ₈ haloalkoxy, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ halocycloalkyl, C ₁ -C ₆ alkylthio, C ₁ -C ₆ haloalkylthio, optionally substituted by R ^3a (C ₁ -C _{6) alkylthio,} C 1 -C _{6 alkylsulfinyl,} C 1 -C _{6 haloalkylsulfinyl,} C 1 -C _{6 alkylsulfonyl,} C 1 -C ₆ ^{haloalkylsulfonyl, -C (O) R 30a,} -C (O) OH , ^{_{hydroxy, -OC (O) R 30e,}} -OS (O) 2 R 30f, -NH 2, -NHR 30g, -N (R 30h) R 30g, ^{mercapto, -SC (O) R 30i,} -SF 5 represents cyano, nitro, phenyl, phenyl optionally substituted by R ^3b, a heterocyclic ring optionally substituted by heterocycle or R ^3b,
R ^3a represents C ₁ -C ₈ alkoxycarbonyl,
R ^3b represents a halogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₈ alkoxy, C ₁ -C ₈ haloalkoxy, cyano or nitro,
R ⁴ represents a hydrogen atom, a halogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₂ -C ₆ haloalkenyl, C ₂ -C ₆ haloalkynyl, C ₁ -C ₈ alkoxy, C ₁ -. C ₈ haloalkoxy, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ halocycloalkyl, C ₁ -C ₆ alkylthio, C ₁ -C ₆ haloalkylthio, optionally substituted by R ^4a (C ₁ -C _{6) alkylthio,} C 1 -C _{6 alkylsulfinyl,} C 1 -C _{6 haloalkylsulfinyl,} C 1 -C _{6 alkylsulfonyl,} C 1 -C ₆ ^{haloalkylsulfonyl, -C (O) R 40a,} -C (O) OH , ^{_{hydroxy, -OC (O) R 40e,}} -OS (O) 2 R 40f, -NH 2, -NHR 40g, -N (R 40h) R 40g, ^{mercapto, -SC (O) R 40i,} -SF 5 represents cyano, nitro, phenyl, phenyl optionally substituted by R ^4b, a heterocyclic ring optionally substituted by heterocycle or R ^4b,
R ^4a represents C ₁ -C ₈ alkoxycarbonyl,
R ^4b represents a halogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₈ alkoxy, C ₁ -C ₈ haloalkoxy, cyano or nitro,
R ⁵ is a hydrogen atom, a halogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₈ alkoxy, C ₁ -C ₈ haloalkoxy, C ₃ -C ₆ cycloalkyl, C ₃ -. C _{6 halocycloalkyl,} C 1 -C _{6 alkylthio,} C 1 -C _{6 haloalkylthio,} C 1 -C _{6 alkylsulfinyl,} C 1 -C _{6 haloalkylsulfinyl,} C 1 -C _{6 alkylsulfonyl,} C 1 -C ₆ It represents ^{haloalkylsulfonyl, -C (O) R 50a,} -C (O) OH, ^{_{hydroxy, -NH 2, -NHR 50g, -N}} (R 50h) R 50g, mercapto, cyano or nitro,
R ⁶ is a hydrogen atom, a halogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₈ alkoxy, C ₁ -C ₈ haloalkoxy, C ₃ -C ₆ cycloalkyl, C ₃ -. C _{6 halocycloalkyl,} C 1 -C _{6 alkylthio,} C 1 -C _{6 haloalkylthio,} C 1 -C _{6 alkylsulfinyl,} C 1 -C _{6 haloalkylsulfinyl,} C 1 -C _{6 alkylsulfonyl,} C 1 -C ₆ It represents ^{haloalkylsulfonyl, -C (O) R 60a,} -C (O) OH, ^{_{hydroxy, -NH 2, -NHR 60g, -N}} (R 60h) R 60g, mercapto, cyano or nitro,
R ⁷ is a hydrogen atom, a halogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₈ alkoxy, C ₁ -C ₈ haloalkoxy, C ₁ -C ₆ alkylthio, C ₁ -C. ₆ haloalkylthio, C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ haloalkylsulfinyl, C ₁ -C ₆ alkylsulfonyl, C ₁ -C ₆ haloalkylsulfonyl, mercapto, -SF ₅ , cyano or nitro,
R ⁸ represents a hydrogen atom, a halogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₈ alkoxy, C ₁ -C ₈ haloalkoxy or cyano,
A ^1a is optionally substituted by hydrogen _atom, C 1 -C _{6 alkyl,} C 1 -C ₆ ^haloalkyl, optionally substituted by _{^{A 1a-a (C 1 -C}} 6) ^{alkyl, A 1a-a} _(C 1 -C _{6) haloalkyl,} C 2 -C _{6 alkenyl,} C 2 -C _{6 haloalkenyl,} C 2 -C _{6 alkynyl,} C 2 -C _{6 haloalkynyl,} C 1 -C _{8 alkoxy,} C 1 -C ₈ haloalkoxy, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ halocycloalkyl, C ₃ -C ₆ cycloalkyl(C ₁ -C ₆ )alkyl, C ₃ -C ₆ halocycloalkyl (C ₁ -C) _{6) alkyl,} C 1 -C _{6 alkylthio,} C 1 -C _{6 haloalkylthio,} C 1 -C _{6 alkylsulfinyl,} C 1 -C _{6 haloalkylsulfinyl,} C 1 -C _{6 alkylsulfonyl,} C 1 -C ₆ haloalkylsulfonyl , C(O)R ^10a , hydroxy or cyano,
A ^1a-a is C ₁ -C ₈ alkoxy, C ₁ -C ₈ haloalkoxy, C ₁ -C ₈ alkoxycarbonyl, C ₁ -C ₈ haloalkoxycarbonyl, C ₁ -C ₆ alkylcarbonyl, C ₁ -C. ₆ haloalkylcarbonyl, C ₁ -C ₆ alkylthio, C ₁ -C ₆ haloalkylthio, C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ haloalkylsulfinyl, C ₁ -C ₆ alkylsulfonyl, C ₁ -C ₆ haloalkylsulfonyl Represents hydroxy, cyano,
T _1a represents a hydrogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ haloalkenyl, C ₂ -C ₆ alkynyl, C ₂ -C ₆ haloalkynyl. , C ₁ -C ₈ alkoxy, C ₁ -C ₈ haloalkoxy, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ halocycloalkyl, C ₃ -C ₆ cycloalkyl(C ₁ -C ₆ )alkyl or C Represents a _3- C ₆ halocycloalkyl(C ₁ -C ₆ )alkyl,
Y1, Y2, Y3 and Y4 are each independently a hydrogen atom, a halogen _atom, C 1 -C _{6 alkyl,} C 1 -C ₆ haloalkyl, optionally substituted by ^{Y a} _(C 1 -C ₆₎ alkyl , optionally substituted by ^{Y a} _(C 1 -C _{6) haloalkyl,} C 2 -C _{6 alkenyl,} C 2 -C ₆ haloalkenyl, optionally substituted by ^{Y a} _(C 2 -C ₆₎ alkenyl, C ₂ -C _{6 alkynyl,} C 2 -C ₆ haloalkynyl, optionally substituted by ^{Y b} _(C 2 -C _{6) alkynyl,} C 1 -C _{8 alkoxy,} C 1 -C ₈ haloalkoxy, by ^{Y a} Optionally substituted (C ₁ -C ₈ )alkoxy, C ₂ -C ₆ alkenyloxy, C ₂ -C ₆ haloalkenyloxy, (C ₂ -C ₆ )alkenyloxy optionally substituted with Y ^a , C ₂ -C _{6 alkynyloxy,} C 2 -C ₆ haloalkynyloxy, optionally substituted by ^{Y a} _(C 2 -C _{6) alkynyloxy,} C 3 -C _{6 cycloalkyl,} C 3 -C ₆ halocycloalkyl , _C 3 -C ₆ cycloalkyl _(C 1 -C _{6) alkyl,} C 3 -C ₆ halocycloalkyl _(C 1 -C _{6) alkyl,} C 1 -C _{6 alkylthio,} C 1 -C ₆ haloalkylthio, Y optionally substituted by ^a _(C 1 -C _{6) alkylthio,} C 2 -C _{6 alkenylthio,} C 2 -C ₆ halo alkenylene _thio, C 2 -C _{6 alkynylthio,} C 2 -C ₆ halo alkynylene thio, C ₁ -C _{6 alkylsulfinyl,} C 1 -C ₆ haloalkylsulfinyl, optionally substituted by ^{Y a} _(C 1 -C _{6) alkylsulfinyl,} C 2 -C _{6 alkenylsulfinyl,} C 2 -C ₆ halo alkenylsulfinyl , _C 2 -C _{6 alkynylsulfinyl,} C 2 -C ₆ halo _{alkynylsulfinyl,} C 1 -C _{6 alkylsulfonyl,} C 1 -C ₆ haloalkylsulfonyl, optionally substituted by ^{Y a} _(C 1 -C ₆₎ alkyl _sulfonyl, C 2 -C _{6 alkenylsulfonyl,} C 2 -C ₆ haloalkenyl _sulfonyl, C 2 -C _{6 alkynylsulfonyl,} C 2 -C ₆ haloalkynyl sulfonyl, - C(O)R ^90a , -C(O)NHR ^90b , -C(O)N(R ^90c )R ^90b , -C(O)OH, -C(=NOR ^90d )R ^90a , -C(O). NH _{2, ^{hydroxy, -OC (O) R 90e,}} -OS (O) 2 R 90f, -NH 2, -NHR 90g, -N (R 90h) R 90g, ^{mercapto, -SC (O) R 90i,} - S(O) ₂ NHR ^90j , —S(O) ₂ N(R ^90k )R ^90j , ^—SF ₅ , cyano, nitro, phenyl, optionally substituted by Y ^c , phenyl, heterocycle or Y ^c . Represents a substituted heterocycle,
Y5 and Y6 are each independently a hydrogen atom, a halogen _atom, C 1 -C _{6 alkyl,} C 1 -C _{6 haloalkyl,} C 1 -C _{8 alkoxy,} C 1 -C _{8 haloalkoxy,} C 1 -C _{6 alkylthio,} C 1 -C _{6 haloalkylthio,} C 1 -C _{6 alkylsulfinyl,} C 1 -C _{6 haloalkylsulfinyl,} C 1 -C _{6 alkylsulfonyl,} C 1 -C ₆ haloalkylsulfonyl, mercapto, -SF _5, cyano, Represents phenyl optionally substituted by nitro, phenyl or Y ^c ,
Y ^a is C ₁ -C ₈ alkoxy, C ₁ -C ₈ haloalkoxy, C ₁ -C ₈ alkoxycarbonyl, C ₁ -C ₈ haloalkoxycarbonyl, C ₁ -C ₆ alkylcarbonyl, C ₁ -C ₆ haloalkyl. _carbonyl, C 1 -C _{6 alkylthio,} C 1 -C _{6 haloalkylthio,} C 1 -C _{6 alkylsulfinyl,} C 1 -C _{6 haloalkylsulfinyl,} C 1 -C _{6 alkylsulfonyl,} C 1 -C ₆ haloalkylsulfonyl, hydroxy Or represents cyano,
Y ^b represents C ₁ -C ₆ alkyl, C ₃ -C ₆ cycloalkyl, trimethylsilyl, C ₁ -C ₈ alkoxy, phenyl or phenyl optionally substituted by Y ^b2 ,
Y ^b2 represents C ₁ -C ₆ haloalkyl,
Y ^c represents a halogen _atom, C 1 -C _{6 alkyl,} C 1 -C _{6 haloalkyl,} C 1 -C _{8 alkoxy,} C 1 -C ₈ haloalkoxy, cyano or nitro,
R ^10a , R ^20a , R ^30a , R ^30e , R ^40a , R ^40e , R ^50a , R ^60a and R ^90a are each independently a hydrogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, Represents C ₁ -C ₈ alkoxy or C ₁ -C ₈ haloalkoxy,
^{R 20g, R 20h, R 30f} , R 30g, R 30h, R 30i, R 40f, R 40g, R 40h, R 40i, R 50g, R 50h, R 60g, R 60h, R 90b, R 90c, R 90i , R ^90j and R ^90k each independently represent C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
R ^90d represents a hydrogen atom, C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
R ^90e is a hydrogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₈ alkoxy, C ₁ -C ₈ haloalkoxy, C ₁ -C ₆ alkylamino, C ₁ -C ₆ haloalkyl. Represents amino, di(C ₁ -C ₆ )alkylamino or di(C ₁ -C ₆ )haloalkylamino,
R ^90f represents C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkylamino, C ₁ -C ₆ haloalkylamino, di(C ₁ -C ₆ )alkylamino or di(C ₁ -). C ₆₎ represents halo alkylamino,
R ^90g and R ^90h are each independently C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkylcarbonyl, C ₁ -C ₆ haloalkylcarbonyl, C ₁ -C ₈ alkoxycarbonyl, C ₁ -C _{8 haloalkoxycarbonyl,} C 1 -C ₆ alkylamino _carbonyl, C 1 -C ₆ haloalkylcarbonyl _{aminocarbonyl,} C 1 -C ₆ alkylamino _{thiocarbonyl,} C 1 -C ₆ haloalkylthio aminothiocarbonyl, phenylcarbonyl, C ₁ -C ₆ alkylsulfonyl, C ₁ -C ₆ haloalkylsulfonyl, C ₁ -C ₆ alkylaminosulfonyl or di(C ₁ -C ₆ )alkylaminosulfonyl is represented,
n represents an integer of 0, 1 or 2. ] The condensed heterocyclic compound represented by these, its salt, or those N-oxides. D substituted with -S _(O) n ^{R 1} represents a ring represented by D1,
G ₁ represents C(Y1),
G ₂ represents C(Y2),
G ₃ represents C(Y3),
G ₄ represents C(Y4),
A ² represents C(R ² ),
A ³ represents C(R ³ ),
R ¹ is C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ haloalkenyl, C ₂ -C ₆ alkynyl, C ₂ -C ₆ haloalkynyl, C _3. -C ₆ cycloalkyl(C ₁ -C ₆ )alkyl or C ₃ -C ₆ halocycloalkyl(C ₁ -C ₆ )alkyl,
R ² represents a hydrogen atom, a halogen atom, C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
R ³ is a hydrogen atom, a halogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₈ alkoxy, C ₁ -C ₈ haloalkoxy, C ₁ -C ₆ alkylthio, C ₁ -C. ₆ haloalkylthio, (C ₁ -C ₆ )alkylthio optionally substituted by R ^3a , C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ haloalkylsulfinyl, C ₁ -C ₆ alkylsulfonyl or C ₁ -C ₆ Represents haloalkylsulfonyl,
R ⁴ is a hydrogen atom, a halogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₈ alkoxy, C ₁ -C ₈ haloalkoxy, C ₁ -C ₆ alkylthio, C ₁ -C. ₆ haloalkylthio, (C ₁ -C ₆ )alkylthio optionally substituted by R ^4a , C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ haloalkylsulfinyl, C ₁ -C ₆ alkylsulfonyl or C ₁ -C ₆ Represents haloalkylsulfonyl,
R ⁵ , R ⁶ and R ⁸ each independently represent a hydrogen atom, a halogen atom, C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
R ⁷ represents a hydrogen atom, a halogen atom or C ₁ -C ₆ haloalkyl,
A ^1a represents a hydrogen atom, C ₁ -C ₆ alkyl, (C ₁ -C ₆ )alkyl optionally substituted by A ^1a-a , C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -. Represents C ₈ alkoxy, C ₃ -C ₆ cycloalkyl or C(O)R ^10a ,
A ^1a-a represents C ₁ -C ₈ alkoxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ alkylsulfonyl or cyano,
R ^10a represents a hydrogen atom, C ₁ -C ₆ alkyl or C ₁ -C ₈ alkoxy,
Y1, Y2, Y3 and Y4 are each independently a hydrogen atom, a halogen _atom, C 1 -C _{6 alkyl,} C 1 -C _{6 haloalkyl,} C 2 -C _{6 alkenyl,} C 2 -C ₆ alkynyl, ^{Y b} optionally substituted _(C 2 -C ₆₎ alkynyl _by, C 1 -C _{8 alkoxy,} C 1 -C _{8 haloalkoxy,} C 1 -C _{6 alkylthio,} C 1 -C ₆ haloalkylthio, optionally by ^{Y a} Substituted (C ₁ -C ₆ )alkylthio, C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ haloalkylsulfinyl, C ₁ -C ₆ alkylsulfonyl, C ₁ -C ₆ haloalkylsulfonyl, —C(O)R ^{90a, -C (O) NHR 90b} , -C (O) N (R 90c) R 90b, -C (O) OH, ^{hydroxy, -OC (O) R 90e,} -OS (O) 2 R 90f, - ^{_{NH 2, -NHR 90g, -N (}} R 90h) R 90g, ^{_{mercapto, -SC (O) R 90i,}} -S (O) 2 NHR 90j, -S (O) 2 N (R 90k) R 90j, - SF _5, represents cyano, nitro, phenyl, phenyl optionally substituted by Y ^c, a heterocyclic ring optionally substituted by heterocycle or Y ^c,
Y ^a represents a C ₁ -C ₈ alkoxycarbonyl, the fused heterocyclic compound according to claim 1, a salt thereof, or an N-oxide thereof. D substituted with —S(O) _n R ¹ represents a ring represented by D2,
Q represents a ring represented by Q1,
A ¹ represents N(A ^1a ),
A ² represents C(R ² ),
A ³ represents C(R ³ ),
A ⁴ represents C(R ⁴ ),
A ⁵ represents a nitrogen atom,
R ¹ is C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ haloalkenyl, C ₂ -C ₆ alkynyl, C ₂ -C ₆ haloalkynyl, C _3. -C ₆ cycloalkyl(C ₁ -C ₆ )alkyl or C ₃ -C ₆ halocycloalkyl(C ₁ -C ₆ )alkyl,
R ² represents a hydrogen atom, a halogen atom, C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
R ³ is a hydrogen atom, a halogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₈ alkoxy, C ₁ -C ₈ haloalkoxy, C ₁ -C ₆ alkylchi group, C ₁ -. C ₆ ^{haloalkylthio,} optionally substituted by ^{R 3a} _(C 1 -C _{6) alkylthio,} C 1 -C _{6 alkylsulfinyl,} C 1 -C _{6 haloalkylsulfinyl,} C 1 -C ₆ alkylsulfonyl or _C 1 -C ₆ represents haloalkylsulfonyl,
R ⁴ is a hydrogen atom, a halogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₈ alkoxy, C ₁ -C ₈ haloalkoxy, C ₁ -C ₆ alkylthio, C ₁ -C. ₆ haloalkylthio, (C ₁ -C ₆ )alkylthio optionally substituted by R ^4a , C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ haloalkylsulfinyl, C ₁ -C ₆ alkylsulfonyl or C ₁ -C ₆ Represents haloalkylsulfonyl,
A ^1a represents a hydrogen atom, C ₁ -C ₆ alkyl, (C ₁ -C ₆ )alkyl optionally substituted by A ^1a-a , C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -. Represents C ₈ alkoxy, C ₃ -C ₆ cycloalkyl or C(O)R ^10a ,
A ^1a-a represents C ₁ -C ₈ alkoxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ alkylsulfonyl or cyano,
R ^10a represents a hydrogen atom, C ₁ -C ₆ alkyl or C ₁ -C ₈ alkoxy,
Y5 represents a hydrogen atom, a halogen atom, C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
Y6 represents a hydrogen atom, a halogen atom, C ₁ -C ₆ haloalkyl, fused heterocyclic compound or a salt thereof or their N- oxide according to claim 1, wherein represents phenyl optionally substituted by phenyl or Y ^c. D substituted with —S(O) _n R ¹ represents a ring represented by D3,
Q represents a ring represented by Q1,
G ₁ represents C(Y1),
G ₂ represents C(Y2),
G ₃ represents C(Y3),
G ₄ represents C(Y4),
T ₁ represents N(T _1a ) or a sulfur atom,
A ¹ represents N(A ^1a ),
A ² represents C(R ² ),
A ³ represents C(R ³ ),
A ⁴ represents C(R ⁴ ),
A ⁵ represents a nitrogen atom,
R ¹ is C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ haloalkenyl, C ₂ -C ₆ alkynyl, C ₂ -C ₆ haloalkynyl, C _3. -C ₆ cycloalkyl(C ₁ -C ₆ )alkyl or C ₃ -C ₆ halocycloalkyl(C ₁ -C ₆ )alkyl,
R ² represents a hydrogen atom, a halogen atom, C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
R ³ is a hydrogen atom, a halogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₈ alkoxy, C ₁ -C ₈ haloalkoxy, C ₁ -C ₆ alkylthio, C ₁ -C. ₆ haloalkylthio, (C ₁ -C ₆ )alkylthio optionally substituted by R ^3a , C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ haloalkylsulfinyl, C ₁ -C ₆ alkylsulfonyl or C ₁ -C ₆ Represents haloalkylsulfonyl,
R ⁴ is a hydrogen atom, a halogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₈ alkoxy, C ₁ -C ₈ haloalkoxy, C ₁ -C ₆ alkylthio, C ₁ -C. ₆ haloalkylthio, (C ₁ -C ₆ )alkylthio optionally substituted by R ^4a , C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ haloalkylsulfinyl, C ₁ -C ₆ alkylsulfonyl or C ₁ -C ₆ Represents haloalkylsulfonyl,
A ^1a represents a hydrogen atom, C ₁ -C ₆ alkyl, (C ₁ -C ₆ )alkyl optionally substituted by A ^1a-a , C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -. Represents C ₈ alkoxy, C ₃ -C ₆ cycloalkyl or C(O)R ^10a ,
A ^1a-a represents C ₁ -C ₈ alkoxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ alkylsulfonyl or cyano,
R ^10a represents a hydrogen atom, C ₁ -C ₆ alkyl or C ₁ -C ₈ alkoxy,
T _1a represents a hydrogen atom or C ₁ -C ₆ alkyl,
Y1, Y2, Y3 and Y4 are each independently a hydrogen atom, a halogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₈ alkoxy, C ₁ -C ₈ haloalkoxy, C. ₁ -C _{6 alkylthio,} C 1 -C _{6 haloalkylthio,} C 1 -C _{6 alkylsulfinyl,} C 1 -C _{6 haloalkylsulfinyl,} C 1 -C _{6 alkylsulfonyl,} C 1 -C ₆ haloalkylsulfonyl, cyano or nitro The condensed heterocyclic compound according to claim 1, a salt thereof or an N-oxide thereof. Q represents a ring represented by Q1,
A ¹ represents N(A ^1a ),
R ¹ represents C ₁ -C ₆ alkyl,
R ³ represents a hydrogen atom, a halogen _atom, C 1 -C _{6 haloalkyl,} C 1 -C ₆ ^{haloalkylthio,} optionally substituted by ^{R 3a} _(C 1 -C _{6) alkylthio,} C 1 -C ₆ haloalkylsulfinyl or Represents C ₁ -C ₆ haloalkylsulfonyl,
R ⁴ is a hydrogen atom, a halogen _atom, C 1 -C _{6 haloalkyl,} C 1 -C ₆ ^{haloalkylthio,} optionally substituted by ^{R 4a} _(C 1 -C _{6) alkylthio,} C 1 -C ₆ haloalkylsulfinyl or Represents C ₁ -C ₆ haloalkylsulfonyl,
A ^1a represents a hydrogen atom or C ₁ -C ₆ alkyl, the fused heterocyclic compound according to claim 2, a salt thereof, or an N-oxide thereof. A ⁴ represents C(R ⁴ ),
A ⁵ represents a nitrogen atom,
R ² represents a hydrogen atom,
R ⁴ represents a hydrogen atom or C ₁ -C ₆ haloalkyl,
Y1 represents a hydrogen atom, C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
Y2 is a hydrogen atom, a halogen _atom, C 1 -C _{6 alkyl,} C 1 -C _{6 haloalkyl,} C 2 -C ₆ alkenyl, optionally substituted by ^{Y b} _(C 2 -C ₆₎ alkynyl, _{C 1} - C _{8 alkoxy,} C 1 -C _{6 alkylthio,} C 1 -C ₆ haloalkylthio, optionally substituted by ^{Y a} _(C 1 -C _{6) alkylthio,} C 1 -C _{6 alkylsulfinyl,} C 1 -C ₆ alkyl represents _sulphonyl, -NH 2, ^{-NHR 90 g,} nitro, cyano, phenyl, phenyl optionally substituted by ^{Y c,} thiophen-2-yl, pyridin-3-yl or pyridin-4-yl,
Y3 is hydrogen atom, halogen _atom, C 1 -C _{6 alkyl,} C 1 -C _{6 haloalkyl,} C 2 -C ₆ alkenyl, optionally substituted by ^{Y b} _(C 2 -C ₆₎ alkynyl, _{C 1} - C _{8 alkoxy,} C 1 -C ₆ alkylthio, optionally substituted by ^{Y a} _(C 1 -C _{6) alkylthio,} C 1 -C _{6 alkylsulfinyl,} C 1 -C ₆ alkylsulfonyl, -C (O) R ^90a , -C(O)N( ^R90c ) ^R90b , -C(O)OH, cyano or nitro,
Y4 represents a hydrogen atom, a halogen _atom, C 1 -C _{6 alkyl,} C 1 -C _{6 haloalkyl,} C 1 -C _{8 alkoxy,} C 1 -C _{6 alkylthio,} C 1 -C ₆ alkylsulfonyl, -N ^{(R 90h} ) R represents ^{90 g} or cyano,
Y ^a represents C ₁ -C ₈ alkoxycarbonyl,
Y ^b represents phenyl optionally substituted by C ₃ -C ₆ cycloalkyl, trimethylsilyl, C ₁ -C ₈ alkoxy or Y ^b2 ,
Y ^c represents a halogen atom or a _C 1 -C ₆ haloalkyl,
R ^90a represents C ₁ -C ₆ alkyl or C ₁ -C ₈ alkoxy,
R ^90b and R ^90c each independently represent C ₁ -C ₆ alkyl,
R ^90g represents C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkylcarbonyl, C ₁ -C ₈ alkoxycarbonyl or phenylcarbonyl,
R ^90h represents a C ₁ -C ₆ alkyl, the fused heterocyclic compound according to claim 5, a salt thereof, or an N-oxide thereof. A ⁴ represents a nitrogen atom,
A ⁵ represents C(R ⁵ ),
R ² represents a hydrogen atom,
R ³ represents C ₁ -C ₆ haloalkyl,
R ⁵ represents a hydrogen atom or C ₁ -C ₆ alkyl,
Y1 represents a hydrogen atom,
Y2 represents a hydrogen atom, a halogen atom or a _C 1 -C ₆ haloalkyl,
Y3 represents a hydrogen atom, a halogen atom, C ₁ -C ₆ haloalkyl or cyano,
Y4 represents a hydrogen atom, a halogen atom or a C ₁ -C ₈ fused heterocyclic compound or a salt thereof or a N- oxide according to claim 5, wherein the alkoxy. Q represents a ring represented by Q2,
A ⁴ represents a nitrogen atom or C(R ⁴ ),
A ⁵ represents a nitrogen atom or C(R ⁵ ),
(However, the case where both A ⁴ and A ⁵ represent a nitrogen atom is excluded)
R ¹ represents C ₁ -C ₆ alkyl,
R ² represents a hydrogen atom,
R ³ represents a hydrogen atom, a halogen _atom, C 1 -C _{6 haloalkyl,} C 1 -C ₆ ^{haloalkylthio,} optionally substituted by ^{R 3a} _(C 1 -C _{6) alkylthio,} C 1 -C ₆ haloalkylsulfinyl or Represents C ₁ -C ₆ haloalkylsulfonyl,
R ⁴ is a hydrogen atom, a halogen _atom, C 1 -C _{6 haloalkyl,} C 1 -C ₆ ^{haloalkylthio,} optionally substituted by ^{R 4a} _(C 1 -C _{6) alkylthio,} C 1 -C ₆ haloalkylsulfinyl or The fused heterocyclic compound according to claim 2, which represents C ₁ -C ₆ haloalkylsulfonyl, a salt thereof, or an N-oxide thereof. A ⁴ represents a nitrogen atom,
A ⁵ represents C(R ⁵ ),
R ³ represents C ₁ -C ₆ haloalkyl,
R ⁵ represents a hydrogen atom or C ₁ -C ₆ alkyl,
R ⁶ represents a hydrogen atom, a halogen atom or C ₁ -C ₆ alkyl,
Y1 and Y4 represent a hydrogen atom,
Y2 represents a hydrogen atom, a halogen atom or a _C 1 -C ₆ haloalkyl,
Y3 is hydrogen atom or a C ₁ -C ₆ fused heterocyclic compound or a salt thereof or a N- oxide according to claim 8, wherein representing the haloalkyl. Q represents a ring represented by Q3,
A ⁴ represents a nitrogen atom or C(R ⁴ ),
A ⁵ represents a nitrogen atom or C(R ⁵ ),
(However, the case where both A ⁴ and A ⁵ represent a nitrogen atom is excluded)
R ¹ represents C ₁ -C ₆ alkyl,
R ² represents a hydrogen atom,
R ³ represents a hydrogen atom, a halogen _atom, C 1 -C _{6 haloalkyl,} C 1 -C ₆ ^{haloalkylthio,} optionally substituted by ^{R 3a} _(C 1 -C _{6) alkylthio,} C 1 -C ₆ haloalkylsulfinyl or Represents C ₁ -C ₆ haloalkylsulfonyl,
R ⁴ is a hydrogen atom, a halogen _atom, C 1 -C _{6 haloalkyl,} C 1 -C ₆ ^{haloalkylthio,} optionally substituted by ^{R 4a} _(C 1 -C _{6) alkylthio,} C 1 -C ₆ haloalkylsulfinyl or The fused heterocyclic compound according to claim 2, which represents C ₁ -C ₆ haloalkylsulfonyl, a salt thereof, or an N-oxide thereof. A ⁴ represents a nitrogen atom,
A ⁵ represents C(R ⁵ ),
R ³ represents C ₁ -C ₆ haloalkyl,
R ⁵ represents a hydrogen atom,
R ⁶ represents a hydrogen atom,
Y1 represents a hydrogen atom,
Y2 and Y3 each independently represent a hydrogen atom, a halogen atom or C ₁ -C ₆ haloalkyl,
Y4 represents a hydrogen atom or a halogen atom, The fused heterocyclic compound of Claim 10, its salt, or those N-oxides. Q is a condensed heterocyclic compound or a salt thereof or an N-oxide thereof, according to claim 2, wherein Q represents a ring represented by Q4. R ¹ represents C ₁ -C ₆ alkyl,
R ⁶ represents a hydrogen atom or C ₁ -C ₆ alkyl,
R ⁷ represents C ₁ -C ₆ haloalkyl,
R ⁸ represents a hydrogen atom or C ₁ -C ₆ alkyl,
Y1 and Y4 represent a hydrogen atom,
Y2 represents a hydrogen atom, a halogen atom or a _C 1 -C ₆ haloalkyl,
Y3 is fused heterocyclic compound or a salt thereof or a N- oxide of claim 12 represents a hydrogen atom or a C ₁ -C ₆ haloalkyl. R ¹ represents C ₁ -C ₆ alkyl,
R ² represents a hydrogen atom,
R ³ represents C ₁ -C ₆ haloalkyl,
R ⁴ represents a hydrogen atom,
A ^1a represents C ₁ -C ₆ alkyl,
Y5 represents a hydrogen atom,
Y6 represents phenyl optionally substituted by halogen _atom, C 1 -C ₆ haloalkyl or ^{Y c,}
Y ^c _is fused heterocyclic compound or a salt thereof or a N- oxide according to claim 3, wherein represents a C 1 -C ₆ haloalkyl. R ¹ represents C ₁ -C ₆ alkyl,
R ² represents a hydrogen atom,
R ³ represents C ₁ -C ₆ haloalkyl,
R ⁴ represents a hydrogen atom,
A ^1a represents C ₁ -C ₆ alkyl,
T _1a represents C ₁ -C ₆ alkyl,
Y1, Y3 and Y4 represent a hydrogen atom,
Y2 _is fused heterocyclic compound or a salt thereof or a N- oxide according to claim 4, wherein represents a C 1 -C ₆ haloalkyl. A ¹ represents N(A ^1a ), or an oxygen atom,
R ² represents a hydrogen atom,
R ³ represents C ₁ -C ₆ haloalkyl, C ₁ -C ₆ haloalkylthio, C ₁ -C ₆ haloalkylsulfinyl or C ₁ -C ₆ haloalkylsulfonyl,
R ⁴ represents a hydrogen atom,
R ⁵ represents a hydrogen atom or C ₁ -C ₆ alkyl,
R ⁶ represents a hydrogen atom,
A ^1a represents C ₁ -C ₆ alkyl,
Y1 and Y4 represent a hydrogen atom,
Y2 and Y3 are each independently fused heterocyclic compound or a salt thereof or a N- oxide according to claim 2, wherein represents a hydrogen atom or a C ₁ -C ₆ haloalkyl. A pest control agent comprising, as an active ingredient, one or more selected from the fused heterocyclic compound according to any one of claims 1 to 16 and a salt thereof. A pesticide containing one or more selected from the fused heterocyclic compound according to any one of claims 1 to 16 and a salt thereof as an active ingredient. An agent for controlling internal or ectoparasites of mammals or birds, which comprises, as an active ingredient, one or more selected from the fused heterocyclic compounds according to any one of claims 1 to 16 and salts thereof. The control agent according to claim 19, wherein the ectoparasite is a flea or a tick. An insecticide or acaricide containing, as an active ingredient, one or more selected from the fused heterocyclic compound according to any one of claims 1 to 16 and a salt thereof. A seed treatment agent containing, as an active ingredient, one or more selected from the fused heterocyclic compounds according to any one of claims 1 to 16 and salts thereof. The seed treatment agent according to claim 22, wherein the seed treatment is performed by an immersion treatment. A soil treatment agent containing, as an active ingredient, one kind or two or more kinds selected from the condensed heterocyclic compounds according to any one of claims 1 to 16. The soil treatment agent according to claim 24, wherein the soil treatment is performed by soil irrigation treatment.