JP2012232962A - Substituted acetal compound and method for producing substituted hydroxypropanone compound - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a substituted acetal compound and a production method using the compound.SOLUTION: A method for producing a substituted hydroxypropanone compound expressed by formula (3) is provided, using a substituted acetal compound expressed by formula (1) and a compound expressed by formula (2) as raw materials. In formula (1), Xrepresents a halogen atom, a cyano group or the like; Xrepresents H, a halogen atom or the like; Xrepresents a halogen atom, an alkyl group having 1 to 6 carbon atoms, or the like; Rrepresents H or an alkyl group having 1 to 4 carbon atoms; and X represents a haloalkyl group having 1 to 4 carbon atoms, or the like.

Description

  The present invention relates to a method for producing a substituted hydroxypropanone compound useful as a functional material such as a medical pesticide or an electronic material, or a production intermediate thereof, and a substituted acetal compound useful as a production intermediate thereof.

  Conventionally, substituted isoxazoline compounds are harmful to N- (2,2,2-trifluoroethyl) -4- (5-substituted-5-substituted phenyl-4,5-dihydroisoxazol-3-yl) benzamide and the like. It is known to be used as a biocontrol agent, particularly an insecticide / acaricide, or an internal or ectoparasite control agent for mammals and birds (see Patent Documents 1 and 2). Substituted hydroxypropanone compounds are known as intermediates for the production of substituted isoxazoline compounds, and specific 1- (substituted phenyl) -2,2,2-trihalo-substituted ethanone compounds are used as methods for producing substituted hydroxypropanone compounds. And a specific acetophenone compound are known (for example, see Patent Documents 3 and 4). Regarding substituted acetal compounds, 1- (3,5-dichlorophenyl) -2,2,2-trifluoro-1-trimethylsilyloxy-1-methoxyethane is known as a synthetic intermediate for acetophenone derivatives ( For example, see Patent Documents 3 to 5 and 6.), 1- (4-chloro-3-nitrophenyl) -2,2,2-trifluoroethane-1,1-diol is a synthetic intermediate of a benzimidazole derivative. (For example, refer to Patent Document 7). Furthermore, 1- (3- (1- (dimethylamino) ethyl) phenyl) -2,2,2-trifluoroethane-1,1-diol is known as a selective acetylcholinesterase inhibitor (for example, patent Reference 8). In non-patent literature, 1- (3-bromophenyl) -2,2,2-trifluoroethane-1,1-diol and 1- (3-nitrophenyl) -2,2,2-trifluoroethane- 1,1-diol is known (see, for example, Non-Patent Document 1), 1- (3,4-dichlorophenyl) -2,2,2-trifluoroethane-1,1-diol and 1- ( 3,4,5-trichlorophenyl) -2,2,2-trifluoroethane-1,1-diol is known (for example, see Non-Patent Document 2), and 2,2,2-tri Fluoro-1-isopropyloxy-1-phenylethanol is known (for example, see Non-Patent Document 3). However, no specific method for producing a substituted hydroxypropanone compound using the substituted acetal compound according to the present invention is disclosed.

International Publication No. 2005/085216 International Publication No. 2007/026965 International Publication No. 2007/074789 International Publication No. 2009/001942 International Publication No. 2009/063910 International Publication No. 2009/116577 International Publication No. 2007/110374 EP-A-0 413 667 specification

Journal of Organic Chemistry 1987, 52, 24, 5356 Zhurnal Fizicheskoi Khimii 1994, 68, 8, 1509 Organic Letters 2009, Vol. 11, No. 22, paragraph 5126

  Pest control agents for harmful arthropods in the fields of agriculture, horticulture and livestock / hygiene (agricultural and horticultural insecticides, acaricides, mammals as domestic animals and pets, and insects inside or outside parasites) , Household and commercial hygiene pests and unpleasant pest control agents), which is effective against a wide range of pest species and has acquired resistance to existing insecticides and acaricides Substituted isoxazoline compounds exhibiting excellent control effects exhibit control effects at extremely low doses, have low persistence and light environmental impact, and are adversely affected by non-target organisms such as mammals, fish and beneficial insects It is an excellent pest control agent that has little effect on water. In order to produce such substituted isoxazoline compounds stably industrially and put to practical use, the development of more efficient production methods and the development of useful production intermediates used in such production methods are always required. ing.

  As a result of intensive studies aimed at solving the above problems, the present inventors have found a substituted acetal compound represented by the following general formula (1), and represented by the following general formula (3) using the compound. The present invention was completed by finding that the production intermediate substituted hydroxypropanone compound can be efficiently produced.

  That is, the present invention relates to the following [1] to [12].

  [1] General formula (1):

[Wherein, X ¹ represents a hydrogen atom, a halogen atom, cyano, nitro, —SF ₅ , C ₁ -C ₄ haloalkyl, C ₁ -C ₄ haloalkoxy or C ₁ -C ₄ haloalkylthio,
X ² represents a hydrogen atom, a halogen atom, a C ₁ -C ₄ haloalkyl, a C ₁ -C ₄ haloalkoxy or a C ₁ -C ₄ haloalkylthio,
X ³ represents a hydrogen atom, a halogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₄ haloalkyl or C ₁ -C ₄ haloalkoxy,
R ¹ represents a hydrogen atom or C ₁ -C ₄ alkyl;
X represents a C ₁ -C ₄ haloalkyl or _C 3 -C ₆ halocycloalkyl. ]
Or a salt thereof.

[2] In general formula (1),
X ¹ represents a halogen atom, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ haloalkoxy or C ₁ -C ₄ haloalkylthio;
X ³ represents a hydrogen atom, a halogen atom, C ₁ -C ₄ haloalkyl or C ₁ -C ₄ haloalkoxy,
R ¹ is a substituted acetal compound or a salt thereof according to the above [1], wherein C ₁ -C ₄ alkyl is represented.

[3] In general formula (1),
X ³ represents a halogen atom, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ haloalkoxy or C ₁ -C ₄ haloalkylthio;
R ¹ represents methyl or ethyl,
X is the substituted acetal compound or a salt thereof according to the above [2], wherein X represents trifluoromethyl or chlorodifluoromethyl.

[4] In general formula (1),
X ³ represents a substituted acetal compound or a salt thereof according to the above [3], wherein the group represents a hydrogen atom.

[5] In general formula (1),
R ¹ is a substituted acetal compound or a salt thereof according to the above [1], wherein R ¹ represents a hydrogen atom.

[6] In general formula (1),
X ¹ represents a halogen atom, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ haloalkoxy or C ₁ -C ₄ haloalkylthio;
X ³ represents a substituted acetal compound or a salt thereof according to the above [5], wherein X ³ represents a hydrogen atom, a halogen atom, C ₁ -C ₄ haloalkyl or C ₁ -C ₄ haloalkoxy.

[7] In general formula (1),
X ² represents a halogen atom, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ haloalkoxy or C ₁ -C ₄ haloalkylthio,
X ³ represents a hydrogen atom, a fluorine atom, a C ₁ -C ₄ haloalkyl or a C ₁ -C ₄ haloalkoxy,
X is the substituted acetal compound or a salt thereof according to the above [6], wherein X represents trifluoromethyl or chlorodifluoromethyl.

[8] In general formula (1),
X ³ represents the substituted acetal compound or a salt thereof according to the above [7], which represents a hydrogen atom.

[9]
General formula (2):

[Wherein, A ¹ , A ² , A ³ and A ⁴ each independently represent N or CY,
R is, C ₁ -C ₆ alkyl, halogen atom, cyano, ^{_{nitro, -NH 2, -N (R 5}} ) R 4, -OH, -OR 3, benzyloxy, -OSO ₂ R ^3, phenylsulfonyloxy, (Z) phenylsulfonyloxy substituted by _{p1, -C (O) OH,} -C (O) OR 3, -C (O) NH 2, -C (O) N (R 1b) R 1a, -C (S) N (R ^1b ) R ^1a , -LQ, -LN (R ^1c ) R ^1d , C ₁ -C ₆ alkylsulfonyl, C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ alkylthio, -S (O ) represents a substituent selected from _r -L ² -Q ² or D-1 to D-50,
R ³ represents C ₁ -C ₆ alkyl, C ₁ -C ₄ alkoxy (C ₁ -C ₄ ) alkyl, C ₁ -C ₆ haloalkyl or C ₁ -C ₃ haloalkoxy (C ₁ -C ₃ ) haloalkyl. ,
Y is a hydrogen atom, a halogen atom, cyano, nitro, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₆ alkylthio, C _{1 to} C ₆ haloalkylthio, C _{1 to} C ₆ alkylsulfonyl, C _{1 to} C ₆ haloalkylsulfonyl, —NH ₂ or —N (R ⁵ ) R ⁴ , each Y may be the same as each other or They may be different,
Two adjacent Ys may be joined together to form A ⁸ = A ⁹ -A ¹⁰ = A ¹¹
A ⁸ , A ⁹ , A ¹⁰ and A ¹¹ each independently represent N or CY ¹
Y ¹ is a hydrogen atom, a halogen atom, cyano, nitro, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ haloalkylthio, C ₁ -C ₆ alkylsulfonyl, C ₁ -C ₆ haloalkylsulfonyl, —NH ₂ or —N (R ⁵ ) R ⁴ , each Y ¹ may be the same as each other Or they may be different from each other,
R ⁴ is, C ₁ -C ₆ alkyl, -CHO, C ₁ ~C ₆ alkyl carbonyl, C ₁ -C ₆ haloalkylcarbonyl, C ₁ -C ₆ alkoxycarbonyl, C ₁ -C ₆ alkylthiocarbonyl, C ₁ -C ₆ alkoxythiocarbonyl, C ₁ -C ₆ alkyl dithio carbonyl, represents C ₁ -C ₆ alkylsulfonyl or C ₁ -C ₆ haloalkylsulfonyl,
R ⁵ represents a hydrogen atom or C ₁ -C ₆ alkyl,
R ^1a is, C ₁ -C ₆ alkyl, C ₁ -C ₆ alkyl optionally substituted by R ^8, condensed which may C ₃ even though -C ₆ cycloalkyl with the benzene ring, C ₃ -C ₆ alkenyl , C ₃ -C ₆ haloalkenyl, C ₃ -C ₆ ^{alkynyl, -N (R 11) R 10} , -C (O) OR 9, -C (O) NH 2, -C (O) NHR 9, - C (R ⁷ ) = NOR ⁶ , phenyl, phenyl substituted by (Z) _p1 , D-5, D-7, D-10, D-11, D-12, D-14, D-15, D -18, D-31, D-32, D-42, D-43, D-45, D-46, D-48, E-1, E-2, E-3, E-4 or E-7 Represents
R ^1b is a hydrogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₄ alkoxy (C ₁ -C ₄ ) alkyl, cyano (C ₁ -C ₆ ) alkyl, C ₃ -C ₆ alkynyl, -C (O ) Represents R ⁹ or -C (O) OR ⁹ ;
Alternatively, R ^1b may form a C _{2 to} C ₆ alkylene chain together with R ^1a to form a 3- to 7-membered ring together with the nitrogen atom to which R ^1b is bonded. It may contain one oxygen atom, sulfur atom or nitrogen atom,
L represents -C (R ^2a ) (R ^2b )-, -C (R ^2a ) (R ^2b ) CH ₂ -or -CH ₂ C (R ^2a ) (R ^2b )-,
Q represents a halogen atom, cyano, nitro or G-1 to G-5,
R ^1c is a hydrogen atom, -C (O) R ^3a , -C (O) OR ^3a , -C (O) SR ^3a , -C (O) N (R ^3b ) R ^3a , -C (S) N (R ^3b ) R ^3a or -S (O) ₂ R ^3a
R ^1d is a hydrogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₄ alkoxy (C ₁ -C ₄ ) alkyl, C ₁ -C ₄ haloalkoxy (C ₁ -C ₄ ) alkyl, C ₁ -C ₄ alkylthio (C ₁ ~C ₄₎ alkyl, C ₁ -C ₄ alkylsulfonyl (C ₁ ~C ₄₎ alkyl, cyano (C ₁ ~C ₆₎ alkyl, C ₃ -C ₆ cycloalkyl , C ₃ -C ₆ cycloalkyl (C ₁ ~C ₄₎ alkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ ^{alkynyl, -C (O) R 3c,} -C (O) OR 3c, -C ( O) SR ^3c, represent a C ₁ -C ₆ haloalkylthio or C ₁ -C ₆ alkylsulfonyl,
Alternatively, R ^1c together with R ^1d forms a C _{4 to} C ₆ alkylene chain, thereby indicating that a 5 to 7 membered ring may be formed with the nitrogen atom to which R ^1c is bonded. oxygen atom may contain one sulfur atom or a nitrogen atom, and C ₁ -C ₆ alkyl group, -CHO group, C ₁ -C ₆ alkylcarbonyl group, C ₁ -C ₆ haloalkylcarbonyl group, C ₁ ~ C ₆ alkoxycarbonyl group, C ₁ -C ₆ haloalkoxycarbonyl group, C ₁ -C ₆ alkylaminocarbonyl group, C ₁ -C ₆ haloalkylaminocarbonyl group, oxo group or thioxo group may be optionally substituted ,
R ^2a represents a hydrogen atom, cyano, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxycarbonyl, -C (O) NH ₂ or -C a (S) NH _2,
R ^2b represents a hydrogen atom or C ₁ -C ₆ alkyl, or R ^2a and R ^2b together form a C ₂ -C ₅ alkylene chain to form 3- It represents that a 6-membered ring may be formed, and this alkylene chain may contain 1 to 3 oxygen atoms, sulfur atoms or nitrogen atoms,
R ^3a is C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, (C ₁ -C ₄ ) alkyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ halocyclo optionally substituted by R ^4a alkyl, E-1, E-2 , E-4, C 2 ~C 6 alkenyl, C ₂ -C ₆ haloalkenyl, C ₂ -C ₆ alkynyl, phenyl, phenyl substituted by (V) _p1, D- 3, D-4, D-12 to D-14, D-42 or D-43,
R ^3b represents a hydrogen atom or C ₁ -C ₆ alkyl,
R ^3c is a hydrogen atom, C ₁ -C ₄ alkyl, (C ₁ -C ₄ ) alkyl, C ₁ -C ₄ haloalkyl, C ₃ -C ₆ cycloalkyl (C ₁ -C) optionally substituted by R ^3d ₄₎ an alkyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl, phenyl, phenyl substituted by R ^14a, a D-42, D-43 or D-44,
R ^3d represents cyano, nitro, C ₁ -C ₄ alkoxy, C ₁ -C ₆ alkoxycarbonyl, S (O) _r R ^5a , phenyl, D-42, D-43 or D-44,
G-1 to G-5 each represent the following structure,

R ^4a represents cyano, nitro, C ₃ -C ₆ cycloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₆ alkoxycarbonyl, S (O) _r R ^5a , D-42 or D-43,
R ^5a represents C ₁ -C ₄ alkyl,
V represents a halogen atom, cyano, nitro, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, -OH, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, C ₁ -C ₆ alkylsulfonyloxy , C ₁ -C ₆ haloalkylsulfonyloxy, 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, -NH _2, C _{1 ~C 6} alkyl amino, di (C ₁ -C ₆ alkyl) amino, C ₁ -C _{6 alkoxycarbonyl, -C (O) NH 2,} C 1 ~C ₆ alkylaminocarbonyl, C ₁ -C ₆ haloalkylcarbonyl aminocarbonyl, di (C ₁ -C ₆ alkyl) _{aminocarbonyl, -C (S) NH 2,} -S (O) 2 NH 2, C 1 ~C 6 alkyl amino represents sulfonyl or di (C ₁ -C ₆ alkyl) aminosulfonyl, p1 indicates an integer of 2 or more Come, each V is may be the or different from each other the same as each other,
Furthermore, if the two V are adjacent, the two V adjacent able to form a -OCH ₂ O-or -OCH ₂ CH ₂ O-, 5-membered together with the carbon atom to which each of the two V binds A ring or a 6-membered ring may be formed, and at this time, a hydrogen atom bonded to each carbon atom forming the ring may be optionally substituted with a halogen atom,
R ⁶ is a hydrogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ halocycloalkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ haloalkenyl, C ₃ -C ₆ alkynyl, C ₃ -C ₆ haloalkynyl, phenyl, phenyl substituted by _{(Z) p1, D-42} , D-45~D-49, E-1~E-4 or Represents E-7,
R ⁷ is a hydrogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy (C ₁ ~C ₆₎ alkyl, C ₁ -C ₆ alkylthio (C ₁ ~C ₆₎ alkyl , C ₃ -C ₆ cycloalkyl or phenyl,
R ⁸ is a halogen atom, cyano, amino, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ halocycloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ haloalkylthio, C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ haloalkylsulfinyl, C ₁ -C ₆ alkylsulfonyl, C ₁ -C ₆ ^{haloalkylsulfonyl, -C (O) R 14,} -C (O) OR ¹⁴ , -C (O) NH ₂ , -C (O) N (R ¹⁵ ) R ¹⁴ , -C (S) NH ₂ , -C (S) N (R ¹⁵ ) R ¹⁴ , -C (R ⁷ ) = NOR ⁶ , phenyl, phenyl substituted by (Z) _p1 , D-1 to D-50 or E-1 to E-8,
D-1 to D-50 each represents an aromatic heterocyclic ring represented by the following structural formula,

Z is a halogen atom, cyano, nitro, amino, C ₁ -C ₆ alkyl, optionally substituted by R ¹⁶ (C ₁ ~C ₆₎ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ haloalkylthio, C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ haloalkylsulfinyl, C ₁ -C ₆ alkylsulfonyl, C ₁ ~ C ₆ haloalkylsulfonyl, C ₁ -C _{6 alkoxycarbonyl, -C (O) NH 2,} -C (S) NH 2, -S (O) 2 NH 2, -C (O) N (R 18) R 17 , -C (S) N (R ¹⁸ ) R ¹⁷ , C ₁ -C ₆ alkylaminosulfonyl or di (C ₁ -C ₆ alkyl) aminosulfonyl, p1, p2, p3 or p4 represents an integer of 2 or more When represented, each Z may be the same as or different from each other,
E-1 to E-8 each represent a heterocyclic ring represented by the following structural formula;

R ⁹ is C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy (C ₁ -C ₄ ) alkyl, C ₁ -C ₆ alkylthio (C ₁ -C ₄ ) alkyl, C ₃ -C ₈ cycloalkyl represents C ₃ -C ₆ alkenyl or C ₃ -C ₆ alkynyl,
R ¹⁰ is C ₁ -C ₆ haloalkyl, -C (O) R ¹⁴ , -C (O) OR ¹⁴ , phenyl, phenyl substituted by (Z) _p1 , D-3, D-4, D-18 , D-42, D-45, D-46, D-48 or D-49,
R ¹¹ represents a hydrogen atom, C ₁ -C ₆ alkyl or C ₃ -C ₆ alkynyl,
R ¹² represents C ₁ -C ₆ alkyl, phenyl or phenyl substituted by (Z) _{p 1}
R ¹³ represents C ₁ -C ₄ alkyl, and when q2, q3 or q4 represents an integer of 2 or more, each R ¹³ may be the same as or different from each other, When two R ¹³ are substituted on the same carbon atom, the two R ¹³ together may form an oxo;
R ¹⁴ is C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₃ -C ₆ cycloalkyl (C ₁ -C ₄ ) alkyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₆ alkoxy (C ₁ -C ₆₎ represents alkyl, hydroxy (C ₁ ~C ₆₎ alkyl, phenyl, phenyl substituted by R ^14a, C ₃ ~C ₆ haloalkenyl, a C ₃ -C ₆ alkenyl or C ₃ -C ₆ alkynyl ,
R ^14a is a halogen atom, cyano, nitro, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, C ₁ -C ₆ alkylthio, C ₁ ~ C ₆ haloalkylthio, C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ haloalkylsulfinyl, C ₁ -C ₆ alkylsulfonyl, C ₁ -C ₆ haloalkylsulfonyl, C ₁ -C ₆ alkoxycarbonyl, -C (O) _{NH 2, -S (O) 2} NH 2, C 1 ~C 6 alkyl aminosulfonyl or di (C ₁ -C ₆ alkyl) represent aminosulfonyl,
R ¹⁵ represents a hydrogen atom or C ₁ -C ₆ alkyl,
R ¹⁶ is, -OH, C ₁ -C ₄ alkoxy or C ₁ -C ₄ alkylthio,
R ¹⁷ is a hydrogen atom, C ₁ -C ₆ alkyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ haloalkenyl, C ₃ -C ₆ alkynyl, -C (R ⁵ ) = NOR ¹⁹ , -C (O) OR ¹⁹ , -C (O) NH ₂ , -C (O) N (R ⁵ ) R ¹⁹ , -C (O) NHC (O) R ¹⁹ , -C (O) Represents N (R ⁵ ) C (O) OR ¹⁹ , -N (R ²¹ ) R ²⁰ or phenyl;
R ¹⁸ represents a hydrogen atom, C ₁ -C ₆ alkyl or C ₃ -C ₆ alkynyl,
R ¹⁹ represents C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl or C ₂ -C ₆ alkenyl,
R ²⁰ represents C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxycarbonyl, phenyl, phenyl substituted by R ^20a , D-42-D-46 or D-47;
R ^20a represents a halogen atom, cyano, nitro, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, a C ₁ -C ₆ alkoxy or C ₁ -C ₆ alkylsulfonyl,
R ²¹ represents a hydrogen atom, C ₁ -C ₆ alkyl, C ₃ -C ₆ alkenyl or C ₃ -C ₆ alkynyl,
L ² represents a single bond or a C ₁ -C ₆ alkylene chain,
Q ² is, C ₁ -C ₆ haloalkyl, C ₂ -C ₆ ^{alkynyl, -N (R 23) R 22} , -C (O) N (R 23) R 22, phenyl, substituted by (Z) _p1 Represents phenyl, D-18 to D-20, D-42 to D-46 or D-47;
R ²² is substituted by C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl, phenyl or (Z) _p1 Represents phenyl,
R ²³ represents a hydrogen atom or C ₁ -C ₆ alkyl,
p1 represents an integer of 1 to 5,
p2 represents an integer of 0 to 4,
p3 represents an integer of 0 to 3,
p4 represents an integer of 0 to 2,
p5 represents an integer of 0 or 1,
q2 represents an integer of 0 to 5,
q3 represents an integer of 0 to 7,
q4 represents an integer of 0 to 9,
r represents an integer of 0 to 2;
t represents an integer of 0 or 1. ]
And a compound represented by the general formula (1):

[Wherein, X ¹ , X ² , X ³ , X and R ¹ represent the same meaning as described in [1] above. ]
By reacting with a compound represented by the general formula (3)

[Wherein, A ¹ , A ² , A ³ , A ⁴ , X ¹ , X ² , X ³ , R and X are the same as the contents described in the compounds represented by formula (1) and formula (2); Represents the same meaning. ]
The manufacturing method of the substituted hydroxypropanone compound represented by these.

[10]
R is, C ₁ -C ₄ alkyl, halogen atom, cyano, ^{_{nitro, -NH 2, -N (R 5}} ) R 4, -OH, -OR 3, ^{_{benzyloxy, -OSO 2 R 3, (Z}} ) p1 Phenylsulfonyloxy substituted by -C (O) OH, -C (O) OR ³ , -C (O) NH ₂ , -C (O) N (R ^1b ) R ^1a , -C (S) N (R ^1b ) R ^1a , -LQ, -LN (R ^1c ) R ^1d or -S (O) _r -L ² -Q ² is D-11 to D-14, D-21 to D-24, D- Represents 36-D-40 or D-41,
Y is a hydrogen atom, a halogen atom, cyano, nitro, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ haloalkylsulfonyl or -N (R ⁵⁾ R ⁴ Each Y may be the same as or different from each other;
Two adjacent Ys may be joined together to form C = CC = C,
R ⁴ is, C ₁ -C ₄ represents alkyl, -CHO, C ₁ -C ₄ alkylcarbonyl, a C ₁ -C ₄ alkoxycarbonyl or C ₁ -C ₄ alkylsulfonyl,
R ⁵ represents a hydrogen atom,
R ^1a is C ₁ -C ₆ alkyl, C ₁ -C ₄ alkyl optionally substituted by R ⁸ , -N (R ¹¹ ) R ¹⁰ , -C (O) OR ⁹ , -C (O) NH ₂ , -C (O) NHR ⁹ , -C (R ⁷ ) = NOR ⁶ , phenyl, phenyl substituted by (Z) _p1 , D-5, D-7, D-10, D-11, D-12 , D-14, D-15, D-18, D-31, D-32, D-42, D-43, D-45, D-46, D-48, E-1 or E-7 ,
R ^1b represents a hydrogen atom, C ₁ -C ₆ alkyl, —C (O) R ⁹ or —C (O) OR ⁹ ;
R ^1d is a hydrogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₄ alkoxy (C ₁ -C ₄ ) alkyl, C ₁ -C ₄ haloalkoxy (C ₁ -C ₄ ) alkyl, C ₁ -C ₄ alkylthio (C ₁ ~C ₄₎ alkyl, C ₁ -C ₄ alkylsulfonyl (C ₁ ~C ₄₎ alkyl, cyano (C ₁ ~C ₆₎ alkyl, C ₃ -C ₆ cycloalkyl , C ₃ -C ₆ cycloalkyl (C ₁ ~C ₄₎ represents alkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl, -C a (O) oR ^3c or -C (O) R ^3c,
R ^2a represents a hydrogen atom, cyano, C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
R ^2b represents a hydrogen atom or C ₁ -C ₆ alkyl,
R ⁶ is a hydrogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ halocycloalkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ haloalkenyl, represents C ₃ -C ₆ alkynyl or C ₃ -C ₆ haloalkynyl,
R ⁸ is fluorine atom, chlorine atom, bromine atom, cyano, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ halocycloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, -C ( O) R ¹⁴ , -C (O) OR ¹⁴ , -C (O) NH ₂ , -C (O) N (R ¹⁵ ) R ¹⁴ , -CH = NOR ⁶ , phenyl, substituted by (Z) _p1 Represents phenyl, D-14, D-19, D-31, D-32, D-36, D-42 or E-5;
R ¹⁰ is C ₁ -C ₆ haloalkyl, -C (O) R ¹⁴ , -C (O) OR ¹⁴ , phenyl, phenyl substituted by (Z) _p1 , D-18, D-42 or D-45 Represents
R ¹¹ represents a hydrogen atom,
R ¹³ represents C ₁ -C ₄ alkyl, and when q2, q3 or q4 represents an integer of 2 or more, each R ¹³ may be the same as or different from each other, When two R ¹³ are substituted on the same carbon atom, the two R ¹³ together may form an oxo;
R ¹⁴ is C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₃ -C ₆ cycloalkyl (C ₁ -C ₄ ) alkyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₆ alkoxy (C ₁ -C ₆₎ represents alkyl, C ₃ -C ₆ haloalkenyl, a C ₃ -C ₆ alkenyl or C ₃ -C ₆ alkynyl,
R ¹⁷ is C ₁ -C ₆ alkyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ haloalkenyl, C ₃ -C ₆ alkynyl, -C (O) OR ¹⁹ ,- C (O) NH ₂ , -C (O) N (R ⁵ ) R ¹⁹ , -C (O) NHC (O) R ¹⁹ , -C (O) N (R ⁵ ) C (O) OR ¹⁹ ,- Represents N (R ²¹ ) R ²⁰ or phenyl;
R ¹⁸ represents a hydrogen atom,
R ²¹ represents a hydrogen atom,
Q ² is C ₁ -C ₆ haloalkyl, C ₂ -C ₆ alkynyl, -N (R ²³ ) R ²² , -C (O) N (R ²³ ) R ²² , D-42-D-46 or D- 47
R ²³ represents a hydrogen atom,
p1 represents an integer of 1 or 2,
p2 represents an integer of 0 or 1,
p3 represents an integer of 0 or 1,
p4 represents an integer of 0 or 1,
q2 represents an integer of 0, 1 or 2;
q3 represents an integer of 0, 1 or 2,
q4 represents an integer of 0, 1 or 2,
t represents an integer of 0 or 1,
X ¹ represents a halogen atom, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ haloalkoxy or C ₁ -C ₄ haloalkylthio,
X ³ represents a hydrogen atom, a halogen atom, C ₁ -C ₄ haloalkyl or C ₁ -C ₄ haloalkoxy,
X is the production method of the above-mentioned [9], which represents trifluoromethyl or chlorodifluoromethyl.

[11]
R is, C ₁ -C ₄ alkyl, halogen atom, cyano, _{nitro, -NH 2, -OH, -C (} O) OH, -C (O) OR 3, -C (O) NH 2, -C ( O) N (R ^1b ) R ^1a , -LQ, -LN (R ^1c ) R ^1d , C ₁ -C ₄ alkylsulfonyl or -S (O) _r -L ² -Q ²
R ³ represents C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl,
Y is a hydrogen atom, a halogen atom, cyano, nitro, C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl, each Y may be the even or different from each other the same as each other,
Two adjacent Ys may be joined together to form C = CC = C,
R ^1a is, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkyl optionally substituted by ^{R 8, -N (R 11)} R 10, -C (O) OR 9, -C (O) NHR 9 ^{, -C (R 7) = NOR} 6, represents phenyl, phenyl, D-42, D-43 , D-45, D-46 or D-48 substituted by (Z) _p1,
L represents -C (R ^2a ) (R ^2b )-
Q represents a halogen atom, cyano, nitro, G-1, G-2 or G-4,
R ^1c represents -C (O) R ^3a , -C (O) OR ^3a or -C (O) N (R ^3b ) R ^3a ,
R ^1d is a hydrogen atom, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy (C ₁ -C ₄ ) alkyl, C ₁ -C ₄ haloalkoxy (C ₁ -C ₄ ) represents alkyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ alkenyl or C ₃ -C ₆ alkynyl,
R ^2b represents a hydrogen atom,
R ^3a is C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, (C ₁ -C ₄ ) alkyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ halocyclo optionally substituted by R ^4a Represents alkyl, phenyl or phenyl substituted by (V) _p1 ,
R ^3b represents a hydrogen atom,
R ^4a represents cyano, nitro, C ₃ -C ₆ cycloalkyl, S (O) _r R ^5a , D-42 or D-43,
V represents a halogen atom, cyano, nitro, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, C ₁ -C ₆ alkylsulfonyl, C ₁ ~ C ₆ haloalkylsulfonyl, C ₁ -C ₆ alkoxycarbonyl, C ₁ -C ₆ alkylaminosulfonyl or di (C ₁ -C ₆ alkyl) aminosulfonyl, and when p ₁ represents an integer of 2, each V is They may be the same or different from each other,
R ⁶ represents C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₃ -C ₆ alkenyl or C ₃ -C ₆ alkynyl,
R ⁷ represents a hydrogen atom or C ₁ -C ₄ alkyl,
R ⁸ is a fluorine atom, a chlorine atom, cyano, -C (O) OR ¹⁴ , -C (O) N (R ¹⁵ ) R ¹⁴ , phenyl, phenyl substituted by (Z) _p1 , D-19, D -42 or E-5,
Z is a fluorine atom, a chlorine atom, a bromine atom, cyano, nitro, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ represents alkylsulfonyl, C ₁ -C ₄ alkoxycarbonyl, -C a (O) NH ₂ or C ₁ -C ₄ alkylaminosulfonyl, when p1 represents an integer 2, each Z is They may be the same or different from each other,
R ⁹ represents C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₃ -C ₆ alkenyl or C ₃ -C ₆ alkynyl,
R ¹⁴ is C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₃ -C ₆ cycloalkyl (C ₁ -C ₄ ) alkyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ haloalkenyl, C ₃ -C ₆ alkenyl or C ₃ -C ₆ alkynyl,
L ² represents a single bond, methylene, ethylidene, ethylene or trimethylene,
Q ² represents C ₁ -C ₄ haloalkyl, C ₂ -C ₆ alkynyl or -C (O) N (R ²³ ) R ²² ,
R ²² represents C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ alkenyl or C ₃ -C ₆ alkynyl,
X ² represents a hydrogen atom, a halogen atom, C ₁ -C ₄ haloalkyl or C ₁ -C ₄ haloalkoxy,
X ³ represents a hydrogen atom, a fluorine atom or a chlorine atom, a manufacturing method of the above-mentioned [10], wherein.

[12]
A ¹ and A ² represent a carbon atom,
R is, C ₁ -C ₄ represents alkyl, a fluorine atom, a chlorine atom, a bromine atom, a -C (O) OH, -C ( O) OR 3 or ^{-C (O) N (R 1b} ) R 1a,
R ³ represents C ₁ -C ₄ alkyl,
Y is a hydrogen atom, a fluorine atom, a chlorine atom, nitro, C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl, each Y may be the even or different from each other the same as each other,
Two adjacent Ys may be joined together to form C = CC = C,
R ^1a is, C ₁ -C ₄ alkyl, C optionally substituted by R ⁸ ₁ -C ₄ alkyl, phenyl, (Z) phenyl substituted by _{p1, D-42, D-} 43, D-45, Represents D-46 or D-48,
R ^1b represents a hydrogen atom,
R ⁸ is a fluorine atom, cyano, -C (O) OR ¹⁴ , -C (O) N (R ¹⁵ ) R ¹⁴ , phenyl, phenyl substituted by (Z) _p1 , D-19, D-42 or Represents E-5,
When Z is a fluorine atom, a chlorine atom, a bromine atom, cyano, nitro, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl or C ₁ -C ₄ haloalkoxy, where p1 represents an integer 2, respectively Z may be the same as or different from each other,
R ¹⁴ represents C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₃ -C ₆ cycloalkyl (C ₁ -C ₄ ) alkyl or C ₃ -C ₆ cycloalkyl,
R ¹⁵ represents a hydrogen atom,
q2 represents an integer of 0 or 1,
t represents an integer of 0;
X ² represents a halogen atom, C ₁ -C ₄ haloalkyl or C ₁ -C ₄ haloalkoxy,
X represents trifluoromethyl,
R ¹ represents the hydrogen atom, methyl or ethyl, the production method according to the above [11].

  The present invention has excellent insecticidal / miticidal activity against many agricultural insect pests, spider mites, mammals or birds, or acquired resistance to existing insecticides / miticides. Provided is a new method for producing a substituted hydroxypropanone compound, which is an intermediate for producing a substituted isoxazoline compound exhibiting a sufficient control effect against pests, and a novel substituted acetal compound useful as an intermediate for the production.

  The compound included in the present invention may have an optically active substance resulting from the presence of an asymmetric carbon atom, but the present invention includes all optically active substances or racemates.

  Depending on the substituents, the compounds described in this application may have E- and Z-form geometric isomers. However, the present invention includes these E-form, Z-form or E-form and Z-form in an arbitrary ratio. Including mixtures containing.

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

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

  Alternatively, among the compounds included in the present invention, those that can be converted into an amine salt according to a conventional method include, for example, ammonia, methylamine, ethylamine, propylamine, butylamine, pentylamine, benzylamine, aniline, dimethylamine, Can be a salt of diethylamine, dipropylamine, dibutylamine, dipentylamine, pyrrolidine, piperidine, piperazine, morpholine, dibenzylamine, trimethylamine, triethylamine, tripropylamine, tributylamine, tripentylamine, tribenzylamine, etc. .

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

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

The notation of C _{a to} C _b alkyl in the present specification represents a linear or branched hydrocarbon group having a carbon number of _a to _b , for example, methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, s-butyl group, t-butyl group, n-pentyl group, 1-methylbutyl group, 2-methylbutyl group, 3-methylbutyl group, 1-ethylpropyl group 1,1-dimethylpropyl group, 1,2-dimethylpropyl group, 2,2-dimethylpropyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 1,1-dimethylbutyl group, Specific examples include 1,3-dimethylbutyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group and the like, and each is selected within the range of the designated number of carbon atoms.

  In the present specification, the aromatic heterocyclic group is represented by 2-thienyl group, 3-thienyl group, 2-furyl group, 3-furyl group, 2-pyranyl group, 3-pyranyl group, 4-pyranyl group, 2- Benzofuranyl group, 3-benzofuranyl group, 4-benzofuranyl group, 5-benzofuranyl group, 6-benzofuranyl group, 7-benzofuranyl group, 1-isobenzofuranyl group, 4-isobenzofuranyl group, 5-isobenzofuranyl group Group, 2-benzothienyl group, 3-benzothienyl group, 4-benzothienyl group, 5-benzothienyl group, 6-benzothienyl group, 7-benzothienyl group, 1-isobenzothienyl group, 4-isobenzothienyl group Group, 5-isobenzothienyl group, 2-chromenyl group, 3-chromenyl group, 4-chromenyl group, 5-chromenyl group, 6-chromenyl group, 7-chloro group Nyl group, 8-chromenyl group, 1-pyrrolyl group, 2-pyrrolyl group, 3-pyrrolyl group, 1-imidazolyl group, 2-imidazolyl group, 4-imidazolyl group, 1-pyrazolyl group, 3-pyrazolyl group, 4- Pyrazolyl group, 2-thiazolyl group, 4-thiazolyl group, 5-thiazolyl group, 3-isothiazolyl group, 4-isothiazolyl group, 5-isothiazolyl group, 2-oxazolyl group, 4-oxazolyl group, 5-oxazolyl group, 3- Isoxazolyl group, 4-isoxazolyl group, 5-isoxazolyl group, 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 2-pyrazinyl group, 2-pyrimidinyl group, 4-pyrimidinyl group, 5-pyrimidinyl group, 3- Pyridazinyl group, 4-pyridazinyl group, 1-indolidinyl group, 2-indolidinyl group, 3-indolidyl group Group, 5-indolidinyl group, 6-indolidinyl group, 7-indolidinyl group, 8-indolidinyl group, 1-isoindolyl group, 4-isoindolyl group, 5-isoindolyl group, 1-indolyl group, 2-indolyl group, 3- Indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group, 7-indolyl group, 1-indazolyl group, 2-indazolyl group, 3-indazolyl group, 4-indazolyl group, 5-indazolyl group, 6- Indazolyl group, 7-indazolyl group, 1-purinyl group, 2-prinyl group, 3-prinyl group, 6-purinyl group, 7-purinyl group, 8-purinyl group, 2-quinolyl group, 3-quinolyl group, 4- Quinolyl group, 5-quinolyl group, 6-quinolyl group, 7-quinolyl group, 8-quinolyl group, 1-isoquinolyl group, 3-isoquinolyl group Ryl group, 4-isoquinolyl group, 5-isoquinolyl group, 6-isoquinolyl group, 7-isoquinolyl group, 8-isoquinolyl group, 1-phthalazinyl group, 5-phthalazinyl group, 6-phthalazinyl group, 2-naphthyridinyl group, 3- Naphthyridinyl group, 4-naphthyridinyl group, 2-quinoxalinyl group, 5-quinoxalinyl group, 6-quinoxalinyl group, 2-quinazolinyl group, 4-quinazolinyl group, 5-quinazolinyl group, 6-quinazolinyl group, 7-quinazolinyl group, 8- Quinazolinyl group, 3-cinnolinyl group, 4-cinnolinyl group, 5-cinnolinyl group, 6-cinnolinyl group, 7-cinnolinyl group, 8-cinnolinyl group, 2-ptenidinyl group, 4-ptenidinyl group, 6-ptenidinyl group, 7- Specific examples include a ptenidinyl group and a 3-furazanyl group.

  Examples of the heterocyclic group in the present specification include, in addition to the above aromatic heterocyclic group, for example, 2-tetrahydrofuranyl group, 3-tetrahydrofuranyl group, 2-tetrahydropyranyl group, 3-tetrahydropyranyl group, 4-tetrahydro Pyranyl group, 1-pyrrolidinyl group, 2-pyrrolidinyl group, 3-pyrrolidinyl group, 1-pyrrolinyl group, 2-pyrrolinyl group, 3-pyrrolinyl group, 4-pyrrolinyl group, 5-pyrrolinyl group, 1-imidazolidinyl group, 2 -Imidazolidinyl group, 4-imidazolidinyl group, 1-imidazolinyl group, 2-imidazolinyl group, 4-imidazolinyl group, 1-pyrazolidinyl group, 3-pyrazolidinyl group, 4-pyrazolidinyl group, 1-pyrazolinyl group, 2-pyrazolinyl group, 3 -Pyrazolinyl group, 4-pyrazolinyl group, 5-pyrazolinyl group, 1- Peridyl group, 2-piperidyl group, 3-piperidyl group, 4-piperidyl group, 1-piperazinyl group, 2-piperazinyl group, 3-piperazinyl group, 1-indolinyl group, 2-indolinyl group, 3-indolinyl group, 4- Indolinyl group, 5-indolinyl group, 6-indolinyl group, 7-indolinyl group, 1-isoindolinyl group, 2-isoindolinyl group, 4-isoindolinyl group, 5-isoindolinyl group, 2-quinuclidinyl group, 3-quinuclidinyl group, 4- Quinuclidinyl group, 2-morpholinyl group, 3-morpholinyl group, 4-morpholinyl group, 1-azetidinyl group, 2-azetidinyl group, 3-azetidinyl group, 1-azetidinonyl group, 3-azetidinonyl group, 4-azetidinonyl group and the like It is done.

In the present specification, C _a -C _b haloalkyl is represented by a linear or branched chain consisting of _a to _b carbon atoms in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom. Represents a hydrocarbon group, and when substituted by two or more halogen atoms, the halogen atoms may be the same as or different from each other. For example, fluoromethyl group, chloromethyl group, bromomethyl group, iodomethyl group, difluoromethyl group, chlorofluoromethyl group, dichloromethyl group, bromofluoromethyl group, trifluoromethyl group, chlorodifluoromethyl group, dichlorofluoromethyl group, trichloromethyl Group, bromodifluoromethyl group, bromochlorofluoromethyl group, dibromofluoromethyl group, 2-fluoroethyl group, 2-chloroethyl group, 2-bromoethyl group, 2,2-difluoroethyl group, 2-chloro-2-fluoroethyl Group, 2,2-dichloroethyl group, 2-bromo-2-fluoroethyl group, 2,2,2-trifluoroethyl group, 2-chloro-2,2-difluoroethyl group, 2,2-dichloro-2 -Fluoroethyl group, 2,2,2-trichloroethyl group, 2-bromo-2,2-difluoroethyl group, 2-bromo-2-chloro-2-fluoroethyl group, 2-butyl Lomo-2,2-dichloroethyl group, 1,1,2,2-tetrafluoroethyl group, pentafluoroethyl group, 1-chloro-1,2,2,2-tetrafluoroethyl group, 2-chloro-1 1,2,2-tetrafluoroethyl group, 1,2-dichloro-1,2,2-trifluoroethyl group, 2-bromo-1,1,2,2-tetrafluoroethyl group, 2-fluoropropyl Group, 2-chloropropyl group, 2-bromopropyl group, 2-chloro-2-fluoropropyl group, 2,3-dichloropropyl group, 2-bromo-3-fluoropropyl group, 3-bromo-2-chloropropyl group Group, 2,3-dibromopropyl group, 3,3,3-trifluoropropyl group, 3-bromo-3,3-difluoropropyl group, 2,2,3,3-tetrafluoropropyl group, 2-chloro- 3,3,3-trifluoropropyl group, 2,2,3,3,3-pentafluoropropyl group, 1,1,2,3,3,3-hexafluoropropyl group, heptafluoropropyl group, 2, 3-dichloro-1,1,2,3,3-pentaph Oropropyl group, 2-fluoro-1-methylethyl group, 2-chloro-1-methylethyl group, 2-bromo-1-methylethyl group, 2,2,2-trifluoro-1- (trifluoromethyl) ethyl Group, 1,2,2,2-tetrafluoro-1- (trifluoromethyl) ethyl group, 2-fluorobutyl group, 2-chlorobutyl group, 2,2,3,3,4,4-hexafluorobutyl group 2,2,3,4,4,4-hexafluorobutyl group, 2,2,3,3,4,4-hexafluorobutyl group, 2,2,3,3,4,4,4-hepta Fluorobutyl group, 1,1,2,2,3,3,4,4-octafluorobutyl group, nonafluorobutyl group, 4-chloro-1,1,2,2,3,3,4,4- Octafluorobutyl group, 2-fluoro-2-methylpropyl group, 1,2,2,3,3,3-hexafluoro-1- (trifluoromethyl) propyl group, 2-chloro-1,1-dimethylethyl Group, 2-bromo-1,1-dimethylethyl group, 5-chloro-2,2,3,4,4,5,5-heptafluoropentyl group, tridecafluorohexyl Group, etc. As a specific example, it may be selected from the range of the specified number of carbon atoms.

The notation of cyano (C _a -C _b ) alkyl in the present specification is linear or branched having a carbon number of _a to _b , wherein a hydrogen atom bonded to a carbon atom is optionally substituted with a cyano group Represents a chain alkyl group, for example, cyanomethyl group, 1-cyanoethyl group, 2-cyanoethyl group, 2-cyanopropyl group, 3-cyanopropyl group, 2-cyanobutyl group, etc. Selected in the range of the number of carbon atoms.

In the present specification, C _{a to} C _b cycloalkyl represents a cyclic hydrocarbon group having _a to _b carbon atoms, and forms a monocyclic or complex ring structure having 3 to 6 members. I can do it. Each ring may be optionally substituted with an alkyl group within the range of the specified number of carbon atoms. For example, cyclopropyl group, 1-methylcyclopropyl group, 2-methylcyclopropyl group, 2,2-dimethylcyclopropyl group, 2,2,3,3-tetramethylcyclopropyl group, cyclobutyl group, cyclopentyl group, 2- Specific examples include methylcyclopentyl group, 3-methylcyclopentyl group, cyclohexyl group, 2-methylcyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, bicyclo [2.2.1] heptan-2-yl group, etc. , Each selected range of carbon atoms.

In the present specification, C _a -C _b halocycloalkyl represents a cyclic hydrocarbon group having _a to _b carbon atoms in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom. And can form monocyclic or complex ring structures from 3 to 6-membered rings. Each ring may be optionally substituted with an alkyl group within the range of the specified number of carbon atoms, and the substitution with a halogen atom may be a ring structure part, a side chain part, They may be both, and when they are substituted by two or more halogen atoms, the halogen atoms may be the same as or different from each other. For example, 2,2-difluorocyclopropyl group, 2,2-dichlorocyclopropyl group, 2,2-dibromocyclopropyl group, 2,2-difluoro-1-methylcyclopropyl group, 2,2-dichloro-1-methyl Cyclopropyl group, 2,2-dibromo-1-methylcyclopropyl group, 2,2,3,3-tetrafluorocyclobutyl group, 2- (trifluoromethyl) cyclohexyl group, 3- (trifluoromethyl) cyclohexyl group , 4- (trifluoromethyl) cyclohexyl group and the like can be mentioned as specific examples, and each is selected within the range of the designated number of carbon atoms.

In the present specification, C _{a to} C _b alkenyl is a linear or branched chain composed of _a to _b carbon atoms and has one or more double bonds in the molecule. Represents a saturated hydrocarbon group, for example, vinyl group, 1-propenyl group, 2-propenyl group, 1-methylethenyl group, 2-butenyl group, 1-methyl-2-propenyl group, 2-methyl-2-propenyl group, 2 -Pentenyl group, 2-methyl-2-butenyl group, 3-methyl-2-butenyl group, 2-ethyl-2-propenyl group, 1,1-dimethyl-2-propenyl group, 2-hexenyl group, 2-methyl Specific examples include 2-pentenyl group, 2,4-dimethyl-2,6-heptadienyl group, 3,7-dimethyl-2,6-octadienyl group, etc. Is done.

In the present specification, C _a -C _b haloalkenyl is a linear or branched chain consisting of _a to _b carbon atoms in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom. And an unsaturated hydrocarbon group having one or more double bonds in the molecule. At this time, when substituted by two or more halogen atoms, these halogen atoms may be the same as or different from each other. For example, 2,2-dichlorovinyl group, 2-fluoro-2-propenyl group, 2-chloro-2-propenyl group, 3-chloro-2-propenyl group, 2-bromo-2-propenyl group, 3-bromo-2 -Propenyl group, 3,3-difluoro-2-propenyl group, 2,3-dichloro-2-propenyl group, 3,3-dichloro-2-propenyl group, 2,3-dibromo-2-propenyl group, 2, 3,3-trifluoro-2-propenyl group, 2,3,3-trichloro-2-propenyl group, 1- (trifluoromethyl) ethenyl group, 3-chloro-2-butenyl group, 3-bromo-2- Butenyl group, 4,4-difluoro-3-butenyl group, 3,4,4-trifluoro-3-butenyl group, 3-chloro-4,4,4-trifluoro-2-butenyl group, 3-bromo- A 2-methyl-2-propenyl group or the like is given as a specific example, and is selected within the range of each designated number of carbon atoms.

In the present specification, C _a -C _b alkynyl is a linear or branched chain having a carbon number of _a to _b , and is unsaturated having one or more triple bonds in the molecule. Represents a hydrocarbon group, for example, ethynyl group, 1-propynyl group, 2-propynyl group, 2-butynyl group, 1-methyl-2-propynyl group, 2-pentynyl group, 1-methyl-2-butynyl group, 1, Specific examples include a 1-dimethyl-2-propynyl group, a 2-hexynyl group, and the like, and each is selected within the range of the designated number of carbon atoms.

The notation of C _a -C _b alkoxy in the present specification represents an alkyl-O— group having the above-mentioned meaning consisting of _a to _b carbon atoms, for example, methoxy group, ethoxy group, n-propyloxy group, Specific examples include i-propyloxy group, n-butyloxy group, i-butyloxy group, s-butyloxy group, t-butyloxy group, n-pentyloxy group, n-hexyloxy group, etc. It is selected in the range of the number of atoms.

The notation of C _a -C _b haloalkoxy in the present specification represents a haloalkyl-O— group having the above-mentioned meaning consisting of _a to _b carbon atoms, for example, difluoromethoxy group, trifluoromethoxy group, chlorodifluoro Methoxy group, bromodifluoromethoxy group, 2-fluoroethoxy group, 2-chloroethoxy group, 2,2,2-trifluoroethoxy group, 1,1,2,2, -tetrafluoroethoxy group, 2-chloro-1 , 1,2-trifluoroethoxy group, 2-bromo-1,1,2-trifluoroethoxy group, pentafluoroethoxy group, 2,2-dichloro-1,1,2-trifluoroethoxy group, 2,2 , 2-trichloro-1,1-difluoroethoxy group, 2-bromo-1,1,2,2-tetrafluoroethoxy group, 2,2,3,3-tetrafluoropropyloxy group, 1,1,2, 3,3,3-hexafluoropropyloxy group, 2,2,2-trifluoro-1- (trifluoromethyl) ethoxy group, Data fluoropropyl group, 2-bromo-1,1,2,3,3,3-hexafluoro-propyloxy group, etc. As a specific example, may be selected from the range of the specified number of carbon atoms.

The notation of benzyloxy in the present specification represents a phenyl-CH ₂ O— group.

The notation of C _a -C _b alkylthio in the present specification represents an alkyl-S-group having the above-mentioned meaning consisting of _a to _b carbon atoms, for example, methylthio group, ethylthio group, n-propylthio group, i Specific examples include -propylthio group, n-butylthio group, i-butylthio group, s-butylthio group, t-butylthio group, n-pentylthio group, n-hexylthio group, etc. Selected.

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

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

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

The notation of C _a -C _b alkylsulfonyl in the present specification represents an alkyl-SO ₂ -group having the above-mentioned meaning consisting of _a to _b carbon atoms, for example, methylsulfonyl group, ethylsulfonyl group, n- Specific examples include propylsulfonyl group, i-propylsulfonyl group, n-butylsulfonyl group, i-butylsulfonyl group, s-butylsulfonyl group, t-butylsulfonyl group, n-pentylsulfonyl group, n-hexylsulfonyl group and the like. Each of which is selected for each specified number of carbon atoms.

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

  The notation of phenylsulfonyloxy in the present specification represents a phenylsulfonyl-O— group.

The notation of C _a -C _b alkylsulfonyloxy in the present specification represents an alkylsulfonyl-O— group having the above-mentioned meaning consisting of _a to _b carbon atoms, for example, methylsulfonyloxy group, ethylsulfonyloxy group N-propylsulfonyloxy group, i-propylsulfonyloxy group, n-butylsulfonyloxy group, i-butylsulfonyloxy group, s-butylsulfonyloxy group, t-butylsulfonyloxy group, n-pentylsulfonyloxy group, Specific examples include an n-hexylsulfonyloxy group and the like, and each is selected within the range of the designated number of carbon atoms.

The notation of C _a -C _b haloalkylsulfonyloxy in the present specification represents a haloalkylsulfonyl-O— group having the above-mentioned meaning consisting of _a to _b carbon atoms, for example, difluoromethylsulfonyloxy group, trifluoro Methylsulfonyloxy group, chlorodifluoromethylsulfonyloxy group, bromodifluoromethylsulfonyloxy group, 2,2,2-trifluoroethylsulfonyloxy group, 1,1,2,2-tetrafluoroethylsulfonyloxy group, 2-chloro Specific examples include -1,1,2-trifluoroethylsulfonyloxy group, 2-bromo-1,1,2,2-tetrafluoroethylsulfonyloxy group, etc. Selected.

The notation of C _a -C _b alkylcarbonyl in the present specification represents an alkyl-C (O) — group having the above-mentioned meaning consisting of _a to _b carbon atoms, for example, acetyl group, propionyl group, butyryl group. Specific examples thereof include isobutyryl group, valeryl group, isovaleryl group, 2-methylbutanoyl group, pivaloyl group, hexanoyl group, heptanoyl group and the like.

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

The notation of C _a -C _b alkoxycarbonyl in the present specification represents an alkoxy-C (O) — group having the above-mentioned meaning consisting of _a to _b carbon atoms, such as a methoxycarbonyl group, an ethoxycarbonyl group, Specific examples include n-propyloxycarbonyl group, i-propyloxycarbonyl group, n-butoxycarbonyl group, i-butoxycarbonyl group, t-butoxycarbonyl group, etc., selected within the range of each designated number of carbon atoms Is done.

The notation of C _a -C _b alkylthiocarbonyl in the present specification represents an alkylthio-C (O) -group having the above-mentioned meaning consisting of _a to _b carbon atoms, for example, methylthio-C (O) -group , Ethylthio-C (O)-group, n-propylthio-C (O)-group, i-propylthio-C (O)-group, n-butylthio-C (O)-group, i-butylthio-C (O ) -Group, t-butylthio-C (O) -group and the like are listed as specific examples, and each group is selected within the range of the designated number of carbon atoms.

In the present specification, the expression C _a -C _b alkoxythiocarbonyl represents an alkoxy-C (S) — group having the above-mentioned meaning consisting of _a to _b carbon atoms, for example, methoxy-C (S) — Groups, ethoxy-C (S) -groups, n-propyloxy-C (S) -groups, i-propyloxy-C (S) -groups, etc. Selected by range.

The notation of C _a -C _b alkyldithiocarbonyl in the present specification represents an alkylthio-C (S) — group having the above-mentioned meaning consisting of _a to _b carbon atoms, for example, methylthio-C (S) — Group, ethylthio-C (S)-group, n-propylthio-C (S)-group, i-propylthio-C (S)-group, etc. Selected.

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

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

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

In the present specification, the notation of di (C _a -C _b alkyl) aminosulfonyl means in the above-mentioned meaning that the number of carbon atoms which may be the same or different from each other is _a to _b. Represents a sulfamoyl group substituted by an alkyl group, for example, N, N-dimethylsulfamoyl group, N-ethyl-N-methylsulfamoyl group, N, N-diethylsulfamoyl group, N, N-di- Specific examples include -n-propylsulfamoyl group, N, N-di-n-butylsulfamoyl group and the like, and each is selected within the range of the designated number of carbon atoms.

C _a -C _b cycloalkyl (C _d -C _e ) alkyl, C _a -C _b alkoxy (C _d -C _e ) alkyl or C _a -C _b alkylthio (C _d -C _e ) alkyl, etc. In the notation, a hydrogen atom bonded to a carbon atom is optionally substituted by any C _a -C _b cycloalkyl group, C _a -C _b alkoxy group or C _a -C _b alkylthio group each having the above-mentioned meaning. It represents a linear or branched hydrocarbon group consisting of d to e carbon atoms, and is selected within the range of the respective designated number of carbon atoms.

Optionally substituted by R ⁸ herein (C _a ~C _b) representation of alkyl, by any R ^8, carbon atoms which hydrogen atoms bonded to carbon atom is optionally substituted a~b It represents a linear or branched hydrocarbon group consisting of a plurality of carbon atoms, and is selected within the range of each designated number of carbon atoms. At this time, when there are two or more substituents R ⁸ on each (C _a -C _b ) alkyl group, each R ⁸ may be the same as or different from each other.

Optionally substituted by R ^3d herein (C _a ~C _b) representation of alkyl, by any R ^3d, to b carbon atoms bonded to hydrogen atoms are optionally substituted carbon atoms It represents a linear or branched hydrocarbon group consisting of a plurality of carbon atoms, and is selected within the range of each designated number of carbon atoms. At this time, when two or more substituents R ^3d on each (C _a -C _b ) alkyl group are present, each R ^3d may be the same as or different from each other.

Optionally substituted by R ^4a herein (C _a ~C _b) representation of alkyl, by any R ^4a, to b carbon atoms bonded to hydrogen atoms are optionally substituted carbon atoms It represents a linear or branched hydrocarbon group consisting of a plurality of carbon atoms, and is selected within the range of each designated number of carbon atoms. At this time, when there are two or more substituents R ^4a on each (C _a -C _b ) alkyl group, each R ^4a may be the same as or different from each other.

In the present specification, the notation of phenyl substituted by (Z) _p1 represents a phenyl group in which a hydrogen atom bonded to a carbon atom is optionally substituted by an arbitrary Z. At this time, when two or more substituents Z on the phenyl group are present, each Z may be the same as or different from each other.

In the present specification, the notation of phenyl substituted by (V) _p1 represents a phenyl group in which a hydrogen atom bonded to a carbon atom is optionally substituted by any V. At this time, when two or more substituents V on the phenyl group are present, each V may be the same as or different from each other.

In the present specification, C _a -C _b cycloalkyl, which may be condensed by a benzene ring, is represented by the number of carbon atoms in which a hydrogen atom bonded to two adjacent carbon atoms is optionally substituted by a benzene ring. Represents a cyclic hydrocarbon group composed of a to b groups, and can form a complex ring structure from a 3-membered ring to a 6-membered ring. For example, 1-indane group, 2-indane group, 1,2,3,4-tetrahydro-1-naphthalene group, 1,2,3,4-tetrahydro-2-naphthalene group and the like can be mentioned as specific examples. Selected within the specified number of carbon atoms.

In the present specification, the notation of hydroxy (C _d -C _e ) haloalkyl, C _a -C _b alkoxy (C _d -C _e ) haloalkyl or C _a -C _b haloalkoxy (C _d -C _e ) haloalkyl is as described above. The number of carbon atoms in which a hydrogen atom or a halogen atom bonded to a carbon atom is arbitrarily substituted by any C _a -C _b alkoxy group, C _a -C _b haloalkoxy group or hydroxyl group, A haloalkyl group as defined above, for example 2,2,2-trifluoro-1-hydroxy-1- (trifluoromethyl) ethyl group, difluoro (methoxy) methyl group, 2,2,2-trifluoro -1-methoxy-1- (trifluoromethyl) ethyl group, difluoro (2,2,2-trifluoroethoxy) methyl group, 2,2,2-trifluoro-1- (2,2,2-trifluoro group) Ethoxy) -1- (trifluoromethyl) ethyl group, 3- (1,2-dichloro-1,2,2-trifluoroethoxy)- Specific examples include 1,1,2,2,3,3-hexafluoropropyl group and the like, and each is selected within the range of the designated number of carbon atoms.

In the present specification, [R ^1b represents that a C _{2 to} C ₆ alkylene chain may be formed together with R ^1a to form a 3- to 7-membered ring together with the nitrogen atom to which it is bonded. The alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom.], For example, aziridine, azetidine, pyrrolidine, oxazolidine, thiazolidine, imidazolidine, piperidine, morpholine, thiomorpholine, piperazine , Homopiperidine, heptamethyleneimine and the like, and each is selected within the range of the designated number of atoms.

In the present specification, [R ^1c represents that, together with R ^1d , a C _{4 to} C ₆ alkylene chain may be formed to form a 5- to 7-membered ring with the nitrogen atom to which it is bonded, The alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and may be optionally substituted with an oxo group or a thioxo group.], Etc., as specific examples of notation such as aziridine, azetidine, Azetidin-2-one, pyrrolidine, pyrrolidin-2-one, oxazolidine, oxazolidine-2-one, oxazolidine-2-thione, thiazolidine, thiazolidine-2-one, thiazolidine-2-thione, imidazolidine, imidazolidine-2- ON, imidazolidine-2-thione, piperidine, piperidin-2-one, piperidin-2-thione, 2H-3,4,5,6-tetrahydro-1,3-oxazin-2-one, 2H-3,4 , 5,6-Tetra Dro-1,3-oxazine-2-thione, morpholine, 2H-3,4,5,6-tetrahydro-1,3-thiazin-2-one, 2H-3,4,5,6-tetrahydro-1, Examples include 3-thiazin-2-thione, thiomorpholine, perhydropyrimidin-2-one, piperazine, homopiperidine, homopiperidin-2-one, and heptamethyleneimine. The

In the present specification, [R ^2a and R ^2b are combined to form a C _{2 to} C ₅ alkylene chain, thereby forming a 3- to 6-membered ring together with the carbon atoms to be bonded. In some cases, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom.], For example, cyclopropane ring, cyclobutane ring, cyclopentane ring, tetrahydrofuran ring, tetrahydrothiophene ring, pyrrolidine ring , A cyclohexane ring, a tetrahydropyran ring, a tetrahydrothiopyran ring, a piperidine ring, a cycloheptane ring, an oxepane ring, a thiepan ring, an azepane ring, and the like.

Among the compounds of the present invention represented by the general formula (1), those in which R ¹ represents C ₁ -C ₄ alkyl can be produced, for example, by the following method.

  Manufacturing method A

General formula (4) [wherein X, X ¹ , X ² and X ³ each have the same meaning as described above. If necessary, the compound represented by the general formula (1) [wherein X, X ¹ , X ² and X ³ are Each represents the same meaning as described above, and R ¹ represents C ₁ -C ₄ alkyl. This invention compound represented by this can be obtained.

  When a solvent is used, the solvent used is not particularly limited as long as it does not inhibit the progress of the reaction. For example, hexane, heptane, cyclohexane, toluene, xylene, tetrahydrofuran, dimethoxyethane, diethyl ether, diisopropyl ether, cyclopentylmethyl Examples include ether, ethyl acetate, butyl acetate, acetonitrile, dichloromethane, dichloroethane, dioxane, N, N-dimethylformamide, and dimethyl sulfoxide. These solvents may be used alone or as a mixture of two or more thereof.

  Examples of the alcohol include methanol, ethanol, n-propanol, i-propanol, n-butanol, i-butanol, s-butanol, t-butanol and the like, and 1 equivalent of the compound represented by the general formula (4) It can be used in an amount of 1 to 120 equivalents.

  The reaction temperature can be set to any temperature from -20 to 150 ° C, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but can usually be arbitrarily set in the range of 0.5 to 72 hours. .

  In general, for example, 1 to 100 equivalents of an alcohol such as methanol or ethanol is used for 1 equivalent of the compound represented by the general formula (4), and the reaction is performed at a temperature range of 0 to 100 ° C. for 1 to 48 hours. It is preferred to do so.

  The target compound of the present invention can be obtained by subjecting the compound represented by the general formula (1) produced by this method to ordinary post-treatment such as direct concentration. Further, each can be used as it is in the next step without isolation / purification.

  Some of the compounds represented by the general formula (4) used here are known compounds, and some of them are available as commercial products. Others can also be synthesized according to general methods described in literatures relating to known compounds.

  Specific examples of the compound of the present invention represented by the general formula (1) that can be produced in this way include the compounds shown in Table 1. However, the compounds in Table 1 are for illustrative purposes, and the present invention is not limited thereto.

In Tables 1 to 7 and 8, the substituent described as Me represents a methyl group, hereinafter “Et” represents an ethyl group, and “n-Pr” and “Pr-n” represent Normal propyl group, i-Pr and Pr-i are isopropyl groups, i-Bu and Bu-i are isobutyl groups, s-Bu and Bu-s are secondary butyl groups. , T-Bu and Bu-t represent a tertiary butyl group, c-Pr represents a cyclopropyl group, and n-Hex represents an n-hexyl group.
[Table 1]

――――――――――――――――― ――――――――――――――――――
X1 X3 X2 X1 X3 X2
――――――――――――――――― ――――――――――――――――――
FHHF OCF ₃ Br
Cl HHF OCF ₃ CF ₃
Br HHF OCF ₃ OCF ₃
IHH Cl FF
CN HH Cl F Cl
NO ₂ HH Cl F Br
CF ₃ HH Cl F CF ₃
CF ₂ CF ₃ HH Cl F OCF ₃
OCF ₃ HH Cl Cl F
OCF ₂ CF ₃ HH Cl Cl Cl
SCF ₃ HH Cl Cl Br
SCF ₂ CF ₃ HH Cl Cl CF ₃
FHF Cl Cl OCF ₃
FH Cl Cl Br F
FH Br Cl Br Cl
FHI Cl Br Br
FH CF ₃ Cl Br CF ₃
FH OCF ₃ Cl Br OCF ₃
FH SCF ₃ Cl CF ₃ F
Cl H Cl Cl CF ₃ Cl
Cl H Br Cl CF ₃ Br
Cl H CF ₃ Cl CF ₃ CF ₃
Cl HI Cl CF ₃ OCF ₃
Cl H OCF ₃ Cl OCF ₃ F
Cl H SCF ₃ Cl OCF ₃ Cl
Br H Br Cl OCF ₃ Br
Br HI Cl OCF ₃ CF ₃
Br H CF ₃ Cl OCF ₃ OCF ₃
Br H OCF ₃ Br FF
Br H SCF ₃ Br F Cl
IHI Br F Br
IH CF ₃ Br F CF ₃
IH OCF ₃ Br F OCF ₃
IH SCF ₃ Br Cl F
CF ₃ H CF ₃ Br Cl Cl
CF ₃ H OCF ₃ Br Cl Br
CF ₃ H SCF ₃ Br Cl CF ₃
OCF ₃ H OCF ₃ Br Cl OCF ₃
OCF ₃ H SCF ₃ Br Br F
SCF ₃ H SCF ₃ Br Br Cl
FFH Br Br Br
F Cl H Br Br CF ₃
F Br H Br Br OCF ₃
FIH Br CF ₃ F
F CF ₃ H Br CF ₃ Cl
F OCF ₃ H Br CF ₃ Br
Cl FH Br CF ₃ CF ₃
Cl Cl H Br CF ₃ OCF ₃
Cl Br H Br OCF ₃ F
Cl IH Br OCF ₃ Cl
Cl CF ₃ H Br OCF ₃ Br
Cl OCF ₃ H Br OCF ₃ CF ₃
Br FH Br OCF ₃ OCF ₃
Br Cl H CF ₃ FF
Br Br H CF ₃ F Cl
Br IH CF ₃ F Br
Br CF ₃ H CF ₃ F CF ₃
Br OCF ₃ H CF ₃ F OCF ₃
IFH CF ₃ Cl F
I Cl H CF ₃ Cl Cl
I Br H CF ₃ Cl Br
IIH CF ₃ Cl CF ₃
I CF ₃ H CF ₃ Cl OCF ₃
I OCF ₃ H CF ₃ Br F
CF ₃ FH CF ₃ Br Cl
CF ₃ Cl H CF ₃ Br Br
CF ₃ Br H CF ₃ Br CF ₃
CF ₃ IH CF ₃ Br OCF ₃
CF ₃ CF ₃ H CF ₃ CF ₃ F
CF ₃ OCF ₃ H CF ₃ CF ₃ Cl
OCF ₃ FH CF ₃ CF ₃ Br
OCF ₃ Cl H CF ₃ CF ₃ CF ₃
OCF ₃ Br H CF ₃ CF ₃ OCF ₃
OCF ₃ IH CF ₃ OCF ₃ F
OCF ₃ CF ₃ H CF ₃ OCF ₃ Cl
OCF ₃ OCF ₃ H CF ₃ OCF ₃ Br
SCF ₃ FH CF ₃ OCF ₃ CF ₃
SCF ₃ Cl H CF ₃ OCF ₃ OCF ₃
SCF ₃ Br H OCF ₃ FF
SCF ₃ IH OCF ₃ F Cl
SCF ₃ CF ₃ H OCF ₃ F Br
SCF ₃ OCF ₃ H OCF ₃ F CF ₃
FFF OCF ₃ F OCF ₃
FF Cl OCF ₃ Cl F
FF Br OCF ₃ Cl Cl
FF CF ₃ OCF ₃ Cl Br
FF OCF ₃ OCF ₃ Cl CF ₃
F Cl F OCF ₃ Cl OCF ₃
F Cl Cl OCF ₃ Br F
F Cl Br OCF ₃ Br Cl
F Cl CF ₃ OCF ₃ Br Br
F Cl OCF ₃ OCF ₃ Br CF ₃
F Br F OCF ₃ Br OCF ₃
F Br Cl OCF ₃ CF ₃ F
F Br Br OCF ₃ CF ₃ Cl
F Br CF ₃ OCF ₃ CF ₃ Br
F Br OCF ₃ OCF ₃ CF ₃ CF ₃
F CF ₃ F OCF ₃ CF ₃ OCF ₃
F CF ₃ Cl OCF ₃ OCF ₃ F
F CF ₃ Br OCF ₃ OCF ₃ Cl
F CF ₃ CF ₃ OCF ₃ OCF ₃ Br
F CF ₃ OCF ₃ OCF ₃ OCF ₃ CF ₃
F OCF ₃ F OCF ₃ OCF ₃ OCF ₃
F OCF ₃ Cl
――――――――――――――――― ――――――――――――――――――
Among the compounds of the present invention represented by the general formula (1), those in which R ¹ is represented by a hydrogen atom can be produced, for example, by the following method.

  Manufacturing method B

General formula (4) [wherein X, X ¹ , X ² and X ³ each have the same meaning as described above. If necessary, the compound represented by the general formula (1) [wherein X, X ¹ , X ² and X ³ are each represented by reacting with water using a solvent inert to the reaction, if necessary. Represents the same meaning as above. This invention compound represented by this can be obtained.

  When a solvent is used, the solvent used is not particularly limited as long as it does not inhibit the progress of the reaction. For example, hexane, heptane, cyclohexane, toluene, xylene, tetrahydrofuran, dimethoxyethane, diethyl ether, diisopropyl ether, cyclopentylmethyl Examples include ether, ethyl acetate, butyl acetate, acetonitrile, dichloromethane, dichloroethane, dioxane, N, N-dimethylformamide, and dimethyl sulfoxide. These solvents may be used alone or as a mixture of two or more thereof.

The reaction temperature can be set to any temperature from -20 to 120 ° C, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but can usually be arbitrarily set in the range of 0.5 to 120 hours. In general, for example, 0.5 to 30 parts of a solvent such as acetonitrile or ethyl acetate is used with respect to 1 equivalent of the compound represented by the general formula (4), and 1 to 50 equivalents of water is added. It is preferable to carry out the reaction for 0.5 to 72 hours in the temperature range of ° C.

  The compound represented by the general formula (1) produced by this method is directly concentrated or dissolved in an organic solvent, concentrated after washing with water, or poured into ice water and concentrated after extraction with an organic solvent, and then subjected to usual post-treatment. The desired present compound can be obtained. Further, each can be used as it is in the next step without isolation / purification.

By reacting the compound represented by the general formula (4) and the general formula (1) with a base using a solvent inert to the reaction, if necessary, the general formula (1 ′) [wherein X, X ¹ , X ² and X ³ each have the same meaning as described above, and M represents an alkali metal such as lithium, potassium, sodium and cesium, an alkaline earth metal such as calcium, barium and magnesium, and aluminum. ] It can be set as the metal salt represented by this.

  In addition, if necessary, the compound represented by the general formula (1 ′) is reacted with an acid using a solvent inert to the reaction, and the compound represented by the general formula (4), the general formula ( It can be set as the mixture of the compound represented by the compound represented by 1) or the compound represented by General formula (4), and General formula (1).

  When a solvent is used, the solvent used is not particularly limited as long as it does not inhibit the progress of the reaction. For example, hexane, heptane, cyclohexane, toluene, xylene, tetrahydrofuran, dimethoxyethane, diethyl ether, diisopropyl ether, cyclopentylmethyl Examples include ether, ethyl acetate, butyl acetate, acetonitrile, dichloromethane, dichloroethane, dioxane, N, N-dimethylformamide, dimethyl sulfoxide and water. These solvents may be used alone or as a mixture of two or more thereof.

  Examples of the base include lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide, barium hydroxide, magnesium hydroxide, aluminum hydroxide such as hydroxide, sodium hydrogen carbonate, hydrogen carbonate such as potassium hydrogen carbonate, carbonate Examples thereof include carbonates such as lithium, sodium carbonate, potassium carbonate, cesium carbonate, calcium carbonate, barium carbonate and magnesium carbonate, and organic acid salts such as sodium phenoxide and sodium acetate. These bases may be used alone or two or more of them may be used.

  Examples of the acid include hydrofluoric acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, nitric acid, sulfuric acid, phosphoric acid, chloric acid, perchloric acid, and other inorganic acids, methanesulfonic acid, ethanesulfonic acid, trifluoromethanesulfone. Acids, sulfonic acids such as benzenesulfonic acid, p-toluenesulfonic acid, formic acid, acetic acid, propionic acid, trifluoroacetic acid, fumaric acid, tartaric acid, succinic acid, maleic acid, malic acid, succinic acid, benzoic acid, mandelic acid, ascorbine Examples thereof include carboxylic acids such as acid, lactic acid, gluconic acid and citric acid, and amino acids such as glutamic acid and aspartic acid. These acids may be used alone or two or more of them may be used.

  The reaction temperature can be set to an arbitrary temperature of −50 to 120 ° C., and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but can usually be arbitrarily set within a range of 0.01 to 120 hours.

  In general, for example, 0 to 100 parts of a solvent such as heptane or water is used with respect to 1 equivalent of the compound represented by the general formula (4), and 0 such as sodium hydroxide, potassium hydroxide, or lithium hydroxide is used. It is preferable to add 1 to 10 equivalents of a 1% to saturated aqueous solution and perform the reaction in the temperature range of -30 to 50 ° C for 0.1 to 48 hours.

  The compound represented by the general formula (1 ′) produced by this method is separated in the case of using a solvent that is difficult to dissolve in water, such as heptane, and the aqueous layer is used as it is for the next step reaction. be able to. The aqueous layer may be washed using a solvent such as heptane. Further, an acid such as hydrochloric acid or sulfuric acid is added to the aqueous layer, extraction is performed using a solvent such as heptane, and a general isolation operation such as concentration is performed to obtain the compound represented by the general formula (4). You can also. Furthermore, an acid such as hydrochloric acid or sulfuric acid is added to the aqueous layer, and a solution extracted using a solvent such as heptane can be used as it is in the next step.

Specific examples of the compounds of the present invention represented by the general formula (1) and the general formula (1 ′) that can be produced in this manner include the compounds shown in Table 2. However, the compounds in Table 2 are for illustrative purposes, and the present invention is not limited to these.
[Table 2]

――――――――――――――――― ――――――――――――――――――
X1 X3 X2 X1 X3 X2
――――――――――――――――― ――――――――――――――――――
FHHF OCF ₃ CF ₃
Cl HHF OCF ₃ OCF ₃
IHH Cl FF
CF ₃ HH Cl F Cl
CF ₂ CF ₃ HH Cl F Br
OCF ₃ HH Cl F CF ₃
OCF ₂ CF ₃ HH Cl F OCF ₃
SCF ₃ HH Cl Cl F
SCF ₂ CF ₃ HH Cl Cl Br
FHF Cl Cl CF ₃
FH Cl Cl Cl OCF ₃
FH Br Cl Br F
FHI Cl Br Cl
FH CF ₃ Cl Br Br
FH OCF ₃ Cl Br CF ₃
FH SCF ₃ Cl Br OCF ₃
Cl H Cl Cl CF ₃ F
Cl H Br Cl CF ₃ Cl
Cl H CF ₃ Cl CF ₃ Br
Cl HI Cl CF ₃ CF ₃
Cl H OCF ₃ Cl CF ₃ OCF ₃
Cl H SCF ₃ Cl OCF ₃ F
Br H Br Cl OCF ₃ Cl
Br HI Cl OCF ₃ Br
Br H CF ₃ Cl OCF ₃ CF ₃
Br H OCF ₃ Cl OCF ₃ OCF ₃
Br H SCF ₃ Br FF
IHI Br F Cl
IH CF ₃ Br F Br
IH OCF ₃ Br F CF ₃
IH SCF ₃ Br F OCF ₃
CF ₃ H CF ₃ Br Cl F
CF ₃ H OCF ₃ Br Cl Cl
CF ₃ H SCF ₃ Br Cl Br
OCF ₃ H OCF ₃ Br Cl CF ₃
OCF ₃ H SCF ₃ Br Cl OCF ₃
SCF ₃ H SCF ₃ Br Br F
FFH Br Br Cl
F Cl H Br Br Br
F Br H Br Br CF ₃
FIH Br Br OCF ₃
F CF ₃ H Br CF ₃ F
F OCF ₃ H Br CF ₃ Cl
Cl FH Br CF ₃ Br
Cl Br H Br CF ₃ CF ₃
Cl IH Br CF ₃ OCF ₃
Cl CF ₃ H Br OCF ₃ F
Cl OCF ₃ H Br OCF ₃ Cl
Br FH Br OCF ₃ Br
Br Cl H Br OCF ₃ CF ₃
Br Br H Br OCF ₃ OCF ₃
Br IH CF ₃ FF
Br CF ₃ H CF ₃ F Cl
Br OCF ₃ H CF ₃ F Br
IFH CF ₃ F CF ₃
I Cl H CF ₃ F OCF ₃
I Br H CF ₃ Cl F
IIH CF ₃ Cl Cl
I CF ₃ H CF ₃ Cl Br
I OCF ₃ H CF ₃ Cl CF ₃
CF ₃ FH CF ₃ Cl OCF ₃
CF ₃ Cl H CF ₃ Br F
CF ₃ Br H CF ₃ Br Cl
CF ₃ IH CF ₃ Br Br
CF ₃ CF ₃ H CF ₃ Br CF ₃
CF ₃ OCF ₃ H CF ₃ Br OCF ₃
OCF ₃ FH CF ₃ CF ₃ F
OCF ₃ Cl H CF ₃ CF ₃ Cl
OCF ₃ Br H CF ₃ CF ₃ Br
OCF ₃ IH CF ₃ CF ₃ CF ₃
OCF ₃ CF ₃ H CF ₃ CF ₃ OCF ₃
OCF ₃ OCF ₃ H CF ₃ OCF ₃ F
SCF ₃ FH CF ₃ OCF ₃ Cl
SCF ₃ Cl H CF ₃ OCF ₃ Br
SCF ₃ Br H CF ₃ OCF ₃ CF ₃
SCF ₃ IH CF ₃ OCF ₃ OCF ₃
SCF ₃ CF ₃ H OCF ₃ FF
SCF ₃ OCF ₃ H OCF ₃ F Cl
FFF OCF ₃ F Br
FF Cl OCF ₃ F CF ₃
FF Br OCF ₃ F OCF ₃
FF CF ₃ OCF ₃ Cl F
FF OCF ₃ OCF ₃ Cl Cl
F Cl F OCF ₃ Cl Br
F Cl Cl OCF ₃ Cl CF ₃
F Cl Br OCF ₃ Cl OCF ₃
F Cl CF ₃ OCF ₃ Br F
F Cl OCF ₃ OCF ₃ Br Cl
F Br F OCF ₃ Br Br
F Br Cl OCF ₃ Br CF ₃
F Br Br OCF ₃ Br OCF ₃
F Br CF ₃ OCF ₃ CF ₃ F
F Br OCF ₃ OCF ₃ CF ₃ Cl
F CF ₃ F OCF ₃ CF ₃ Br
F CF ₃ Cl OCF ₃ CF ₃ CF ₃
F CF ₃ Br OCF ₃ CF ₃ OCF ₃
F CF ₃ CF ₃ OCF ₃ OCF ₃ F
F CF ₃ OCF ₃ OCF ₃ OCF ₃ Cl
F OCF ₃ F OCF ₃ OCF ₃ Br
F OCF ₃ Cl OCF ₃ OCF ₃ CF ₃
F OCF ₃ Br OCF ₃ OCF ₃ OCF ₃
――――――――――――――――― ――――――――――――――――――
As this invention compound represented by General formula (5) which can be manufactured by this manufacturing method, the compound shown in Table 3 is specifically mentioned. However, the compounds in Table 3 are for illustrative purposes, and the present invention is not limited thereto.
[Table 3]

X1 X3 X2 R
―――――――――――――――――――――――――――――――――
Cl H Cl F
Cl H Cl OS (O) ₂ Me
Cl H Cl S (O) ₂ Me
―――――――――――――――――――――――――――――――――
As this invention compound represented by General formula (6) which can be manufactured with this manufacturing method, the compound shown in Table 4 is specifically mentioned. However, the compounds in Table 4 are for illustrative purposes, and the present invention is not limited thereto.

  In the table, aromatic complex represented by D-11a, D-11b, D-21a, D-35a, D-36a, D-37a, D-38a, D-39a, D-40a and D-41a Each ring represents the following structure.

[Table 4]

X Y R
―――――――――――――――――――――――――――――――――
CF_Three          H F
CF_Three          H Cl
CF_Three          H Br
CF_Three          H I
CF_Three          H CN
CF_Three          H OH
CF_Three          H OMe
CF_Three          H OCH₂Ph
CF_Three          H OS (O)₂Me
CF_Three          H OS (O)₂CF_Three
CF_Three          H OS (O)₂(Ph-4-Me)
CF_Three          H S (O)₂Me
CF_Three          H S (O)₂CF_Three
CF_Three          H NO₂
CF_Three          H NH₂
CF_Three          H NHC (O) Me
CF_Three          H NHC (O) OMe
CF_Three          H NHC (O) OEt
CF_Three          H Me
CF_Three          H Et
CF_Three          H n-Pr
CF_Three          H CH₂Cl
CF_Three          H CH₂Br
CF_Three          H CH₂OH
CF_Three          H CH₂NH₂
CF_Three          H CH₂NHC (O) Me
CF_Three          H CH₂NHC (O) Et
CF_Three          H CH₂NHC (O) -n-Pr
CF_Three          H CH₂NHC (O) -c-Pr
CF_Three          H CH₂NHC (O) CH₂SMe
CF_Three          H CH₂NHC (O) CH₂S (O)₂Me
CF_Three          H CH₂NHC (O) CH₂SEt
CF_Three          H CH₂NHC (O) CH₂S (O)₂Et
CF_Three          H CH₂NHC (O) CH₂S-n-Pr
CF_Three          H CH₂NHC (O) CH₂S (O)₂-NPR
CF_Three          H CH₂NHC (O) CH₂S-c-Pr
CF_Three          H CH₂NHC (O) CH₂S (O)₂-c-Pr
CF_Three          H CH₂NHC (O) OMe
CF_Three          H CH₂NHC (O) OEt
CF_Three          H CH₂NHC (O) O-n-Pr
CF_Three          H CH₂NHC (O) O-c-Pr
CF_Three          H CH₂NHC (O) NHMe
CF_Three          H CH₂NHC (O) NHEt
CF_Three          H CH₂NHC (O) NH-n-Pr
CF_Three          H CH₂NHC (O) NH-c-Pr
CF_Three          H CH₂NO₂
CF_Three          H CH₂-(G-1)
CF_Three          H CH₂-(G-2)
CF_Three          H C (O) OH
CF_Three          H C (O) OMe
CF_Three          H C (O) OEt
CF_Three          H C (O) O-n-Pr
CF_Three          H C (O) NH₂
CF_Three          H C (O) NHMe
CF_Three          H C (O) NHEt
CF_Three          H C (O) NH-n-Pr
CF_Three          H C (O) NH-c-Pr
CF_Three          H C (O) NHCH₂-c-Pr
CF_Three          H C (O) NHCH₂CF_Three
CF_Three          H C (O) NH (Me) CH₂CF_Three
CF_Three          H C (O) NH (CH₂OMe) CH₂CF_Three
CF_Three          H C (O) NH [C (O) OMe] CH₂CF_Three
CF_Three          H C (O) NHCH₂CH = CH₂
CF_Three          H C (O) NHCH₂CH₂CH₂OMe
CF_Three          H C (O) NHCH = NOMe
CF_Three          H C (O) NHCH = NOEt
CF_Three          H C (O) NHC (Me) = NOMe
CF_Three          H C (O) NHC (Me) = NOEt
CF_Three          H C (O) NHCH₂CH = NOH
CF_Three          H C (O) NHCH₂CH = NOMe
CF_Three          H C (O) NHCH₂(Me) = NOMe
CF_Three          H C (O) NHCH₂CN
CF_Three          H C (O) NHCH₂C (O) OH
CF_Three          H C (O) NHCH₂C (O) OMe
CF_Three          H C (O) NHCH₂C (O) OEt
CF_Three          H C (O) NHCH₂C (O) OCH₂CF_Three
CF_Three          H C (O) NHCH₂C (O) NH₂
CF_Three          H C (O) NHCH₂C (O) NHMe
CF_Three          H C (O) NHCH₂C (O) NMe₂
CF_Three          H C (O) NHCH₂C (O) NHEt
CF_Three          H C (O) NHCH₂C (O) NHCH₂CH₂Cl
CF_Three          H C (O) NHCH₂C (O) NHCH₂CH₂Br
CF_Three          H C (O) NHCH₂C (O) NHCH₂CH₂F
CF_Three          H C (O) NHCH₂C (O) NHCH₂CF_Three
CF_Three          H C (O) NHCH₂C (O) N (Me) CH₂CF_Three
CF_Three          H C (O) N (Me) CH₂C (O) NHCH₂CF_Three
CF_Three          H C (O) NHCH₂C (O) NHCH₂CH₂OH
CF_Three          H C (O) NHCH (Me) C (O) OH
CF_Three          H C (O) NHCH (Me) C (O) OMe
CF_Three          H C (O) NHCH (Me) C (O) NHCH₂CH₂Cl
CF_Three          H C (O) NHCH (Me) C (O) NHCH₂CF_Three
CF_Three          H C (O) NHCH₂Ph
CF_Three          H C (O) NHCH₂(Ph-4-F)
CF_Three          H C (O) NHCH (Me) (Ph-4-F)
CF_Three          H C (O) NHCH (Et) (Ph-4-F)
CF_Three          H C (O) NHCH (CH₂CN) (Ph-4-F)
CF_Three          H C (O) NHCH (CH₂OMe) (Ph-4-F)
CF_Three          H C (O) NHCH [C (O) Me] (Ph-4-F)
CF_Three          H C (O) NHCH [C (O) OMe] (Ph-4-F)
CF_Three          H C (O) NHCH (Ph-4-CN)
CF_Three          H C (O) NHCH₂CH₂Cl
CF_Three          H C (O) NHCH₂-(2-pyridyl)
CF_Three          H C (O) NHCH₂-(4-thiazolyl)
CF_Three          H C (O) NHCH₂-(1,3-dioxolane-2-yl)
CF_Three          H C (O) NHCH₂CH₂SMe
CF_Three          H C (O) NHCH (Me) CH₂SMe
CF_Three          H C (O) NHCH₂CH₂CH₂SMe
CF_Three          H C (O) NHCH₂CH₂S (O) Me
CF_Three          H C (O) NHCH (Me) CH₂S (O) Me
CF_Three          H C (O) NHCH₂CH₂CH₂S (O) Me
CF_Three          H C (O) NHCH₂CH₂S (O)₂Me
CF_Three          H C (O) NHCH (Me) CH₂S (O)₂Me
CF_Three          H C (O) NHCH₂CH₂CH₂S (O)₂Me
CF_Three          H C (O) NHNH₂
CF_Three          H C (O) NHNHMe
CF_Three          H C (O) NHNMe₂
CF_Three          H C (O) NHNHPh
CF_Three          H C (O) NHC (O) OMe
CF_Three          H C (O) NHC (O) OEt
CF_Three          H C (O) NHC (O) NHMe
CF_Three          H C (O) NHC (O) NHEt
CF_Three          H C (O) NHC (O) NH₂
CF_Three          H C (O) NHC (O) NMe₂
CF_Three          H C (O) NHPh
CF_Three          H C (O) NH (Ph-4-Cl)
CF_Three          H C (O) NH (2-pyridyl)
CF_Three          H C (O) NHCH₂C (O) NH-i-Pr
CF_Three          H C (O) NHCH₂C (O) NHCH₂-i-Pr
CF_Three          H C (O) NHCH (Me) C (O) NHCH₂-i-Pr
CF_Three          H C (O) NHCH (Me) C (O) NHCH₂CH₂F
CF_Three          H D-11a
CF_Three          H D-11b
CF_Three          H D-21a
CF_Three          H D-35a
CF_Three          H D-36a
CF_Three          H D-37a
CF_Three          H D-38a
CF_Three          H D-39a
CF_Three          H D-40a
CF_Three          H D-41a
CF_Three          F F
CF_Three          F Cl
CF_Three          F Br
CF_Three          F I
CF_Three          F CN
CF_Three          F OH
CF_Three          F OMe
CF_Three          F OCH₂Ph
CF_Three          F OS (O)₂Me
CF_Three          F OS (O)₂CF_Three
CF_Three          F OS (O)₂(Ph-4-Me)
CF_Three          F S (O)₂Me
CF_Three          F S (O)₂CF_Three
CF_Three          F NO₂
CF_Three          F NH₂
CF_Three          F NHC (O) Me
CF_Three          F NHC (O) OMe
CF_Three          F NHC (O) OEt
CF_Three          F Me
CF_Three          F Et
CF_Three          F n-Pr
CF_Three          F CH₂Cl
CF_Three          F CH₂Br
CF_Three          F CH₂OH
CF_Three          F CH₂NH₂
CF_Three          F CH₂NHC (O) Me
CF_Three          F CH₂NHC (O) Et
CF_Three          F CH₂NHC (O) -n-Pr
CF_Three          F CH₂NHC (O) -c-Pr
CF_Three          F CH₂NHC (O) CH₂SMe
CF_Three          F CH₂NHC (O) CH₂S (O)₂Me
CF_Three          F CH₂NHC (O) CH₂SEt
CF_Three          F CH₂NHC (O) CH₂S (O)₂Et
CF_Three          F CH₂NHC (O) CH₂S-n-Pr
CF_Three          F CH₂NHC (O) CH₂S (O)₂-NPR
CF_Three          F CH₂NHC (O) CH₂S-c-Pr
CF_Three          F CH₂NHC (O) CH₂S (O)₂-c-Pr
CF_Three          F CH₂NHC (O) OMe
CF_Three          F CH₂NHC (O) OEt
CF_Three          F CH₂NHC (O) O-n-Pr
CF_Three          F CH₂NHC (O) O-c-Pr
CF_Three          F CH₂NHC (O) NHMe
CF_Three          F CH₂NHC (O) NHEt
CF_Three          F CH₂NHC (O) NH-n-Pr
CF_Three          F CH₂NHC (O) NH-c-Pr
CF_Three          F CH₂NO₂
CF_Three          F CH₂-(G-1)
CF_Three          F CH₂-(G-2)
CF_Three          F C (O) OH
CF_Three          F C (O) OMe
CF_Three          F C (O) OEt
CF_Three          F C (O) O-n-Pr
CF_Three          F C (O) NH₂
CF_Three          F C (O) NHMe
CF_Three          F C (O) NHEt
CF_Three          F C (O) NH-n-Pr
CF_Three          F C (O) NH-c-Pr
CF_Three          F C (O) NHCH₂-c-Pr
CF_Three          F C (O) NHCH₂CF_Three
CF_Three          F C (O) NH (Me) CH₂CF_Three
CF_Three          F C (O) NH (CH₂OMe) CH₂CF_Three
CF_Three          F C (O) NH [C (O) OMe] CH₂CF_Three
CF_Three          F C (O) NHCH₂CH = CH₂
CF_Three          F C (O) NHCH₂CH₂CH₂OMe
CF_Three          F C (O) NHCH = NOMe
CF_Three          F C (O) NHCH = NOEt
CF_Three          F C (O) NHC (Me) = NOMe
CF_Three          F C (O) NHC (Me) = NOEt
CF_Three          F C (O) NHCH₂CH = NOH
CF_Three          F C (O) NHCH₂CH = NOMe
CF_Three          F C (O) NHCH₂(Me) = NOMe
CF_Three          F C (O) NHCH₂CN
CF_Three          F C (O) NHCH₂C (O) OH
CF_Three          F C (O) NHCH₂C (O) OMe
CF_Three          F C (O) NHCH₂C (O) OEt
CF_Three          F C (O) NHCH₂C (O) OCH₂CF_Three
CF_Three          F C (O) NHCH₂C (O) NH₂
CF_Three          F C (O) NHCH₂C (O) NHMe
CF_Three          F C (O) NHCH₂C (O) NMe₂
CF_Three          F C (O) NHCH₂C (O) NHEt
CF_Three          F C (O) NHCH₂C (O) NHCH₂CH₂Cl
CF_Three          F C (O) NHCH₂C (O) NHCH₂CH₂Br
CF_Three          F C (O) NHCH₂C (O) NHCH₂CH₂F
CF_Three          F C (O) NHCH₂C (O) NHCH₂CF_Three
CF_Three          F C (O) NHCH₂C (O) N (Me) CH₂CF_Three
CF_Three          F C (O) N (Me) CH₂C (O) NHCH₂CF_Three
CF_Three          F C (O) NHCH₂C (O) NHCH₂CH₂OH
CF_Three          F C (O) NHCH (Me) C (O) OH
CF_Three          F C (O) NHCH (Me) C (O) OMe
CF_Three          F C (O) NHCH (Me) C (O) NHCH₂CH₂Cl
CF_Three          F C (O) NHCH (Me) C (O) NHCH₂CF_Three
CF_Three          F C (O) NHCH₂Ph
CF_Three          F C (O) NHCH₂(Ph-4-F)
CF_Three          F C (O) NHCH (Me) (Ph-4-F)
CF_Three          F C (O) NHCH (Et) (Ph-4-F)
CF_Three          F C (O) NHCH (CH₂CN) (Ph-4-F)
CF_Three          F C (O) NHCH (CH₂OMe) (Ph-4-F)
CF_Three          F C (O) NHCH [C (O) Me] (Ph-4-F)
CF_Three          F C (O) NHCH [C (O) OMe] (Ph-4-F)
CF_Three          F C (O) NHCH (Ph-4-CN)
CF_Three          F C (O) NHCH₂CH₂Cl
CF_Three          F C (O) NHCH₂-(2-pyridyl)
CF_Three          F C (O) NHCH₂-(4-thiazolyl)
CF_Three          F C (O) NHCH₂-(1,3-dioxolane-2-yl)
CF_Three          F C (O) NHCH₂CH₂SMe
CF_Three          F C (O) NHCH (Me) CH₂SMe
CF_Three          F C (O) NHCH₂CH₂CH₂SMe
CF_Three          F C (O) NHCH₂CH₂S (O) Me
CF_Three          F C (O) NHCH (Me) CH₂S (O) Me
CF_Three          F C (O) NHCH₂CH₂CH₂S (O) Me
CF_Three          F C (O) NHCH₂CH₂S (O)₂Me
CF_Three          F C (O) NHCH (Me) CH₂S (O)₂Me
CF_Three          F C (O) NHCH₂CH₂CH₂S (O)₂Me
CF_Three          F C (O) NHNH₂
CF_Three          F C (O) NHNHMe
CF_Three          F C (O) NHNMe₂
CF_Three          F C (O) NHNHPh
CF_Three          F C (O) NHC (O) OMe
CF_Three          F C (O) NHC (O) OEt
CF_Three          F C (O) NHC (O) NHMe
CF_Three          F C (O) NHC (O) NHEt
CF_Three          F C (O) NHC (O) NH₂
CF_Three          F C (O) NHC (O) NMe₂
CF_Three          F C (O) NHPh
CF_Three          F C (O) NH (Ph-4-Cl)
CF_Three          F C (O) NH (2-pyridyl)
CF_Three          F C (O) NHCH₂C (O) NH-i-Pr
CF_Three          F C (O) NHCH₂C (O) NHCH₂-i-Pr
CF_Three          F C (O) NHCH (Me) C (O) NHCH₂-i-Pr
CF_Three          F C (O) NHCH (Me) C (O) NHCH₂CH₂F
CF_Three          F D-11a
CF_Three          F D-11b
CF_Three          F D-21a
CF_Three          F D-35a
CF_Three          F D-36a
CF_Three          F D-37a
CF_Three          F D-38a
CF_Three          F D-39a
CF_Three          F D-40a
CF_Three          F D-41a
CF_Three          Cl F
CF_Three          Cl Cl
CF_Three          Cl Br
CF_Three          Cl I
CF_Three          Cl CN
CF_Three          Cl OH
CF_Three          Cl OMe
CF_Three          Cl OCH₂Ph
CF_Three          Cl OS (O)₂Me
CF_Three          Cl OS (O)₂CF_Three
CF_Three          Cl OS (O)₂(Ph-4-Me)
CF_Three          Cl S (O)₂Me
CF_Three          Cl S (O)₂CF_Three
CF_Three          Cl NO₂
CF_Three          Cl NH₂
CF_Three          Cl NHC (O) Me
CF_Three          Cl NHC (O) OMe
CF_Three          Cl NHC (O) OEt
CF_Three          Cl Me
CF_Three          Cl Et
CF_Three          Cl n-Pr
CF_Three          Cl CH₂Cl
CF_Three          Cl CH₂Br
CF_Three          Cl CH₂OH
CF_Three          Cl CH₂NH₂
CF_Three          Cl CH₂NHC (O) Me
CF_Three          Cl CH₂NHC (O) Et
CF_Three          Cl CH₂NHC (O) -n-Pr
CF_Three          Cl CH₂NHC (O) -c-Pr
CF_Three          Cl CH₂NHC (O) CH₂SMe
CF_Three          Cl CH₂NHC (O) CH₂S (O)₂Me
CF_Three          Cl CH₂NHC (O) CH₂SEt
CF_Three          Cl CH₂NHC (O) CH₂S (O)₂Et
CF_Three          Cl CH₂NHC (O) CH₂S-n-Pr
CF_Three          Cl CH₂NHC (O) CH₂S (O)₂-NPR
CF_Three          Cl CH₂NHC (O) CH₂S-c-Pr
CF_Three          Cl CH₂NHC (O) CH₂S (O)₂-c-Pr
CF_Three          Cl CH₂NHC (O) OMe
CF_Three          Cl CH₂NHC (O) OEt
CF_Three          Cl CH₂NHC (O) O-n-Pr
CF_Three          Cl CH₂NHC (O) O-c-Pr
CF_Three          Cl CH₂NHC (O) NHMe
CF_Three          Cl CH₂NHC (O) NHEt
CF_Three          Cl CH₂NHC (O) NH-n-Pr
CF_Three          Cl CH₂NHC (O) NH-c-Pr
CF_Three          Cl CH₂NO₂
CF_Three          Cl CH₂-(G-1)
CF_Three          Cl CH₂-(G-2)
CF_Three          Cl C (O) OH
CF_Three          Cl C (O) OMe
CF_Three          Cl C (O) OEt
CF_Three          Cl C (O) O-n-Pr
CF_Three          Cl C (O) NH₂
CF_Three          Cl C (O) NHMe
CF_Three          Cl C (O) NHEt
CF_Three          Cl C (O) NH-n-Pr
CF_Three          Cl C (O) NH-c-Pr
CF_Three          Cl C (O) NHCH₂-c-Pr
CF_Three          Cl C (O) NHCH₂CF_Three
CF_Three          Cl C (O) NH (Me) CH₂CF_Three
CF_Three          Cl C (O) NH (CH₂OMe) CH₂CF_Three
CF_Three          Cl C (O) NH [C (O) OMe] CH₂CF_Three
CF_Three          Cl C (O) NHCH₂CH = CH₂
CF_Three          Cl C (O) NHCH₂CH₂CH₂OMe
CF_Three          Cl C (O) NHCH = NOMe
CF_Three          Cl C (O) NHCH = NOEt
CF_Three          Cl C (O) NHC (Me) = NOMe
CF_Three          Cl C (O) NHC (Me) = NOEt
CF_Three          Cl C (O) NHCH₂CH = NOH
CF_Three          Cl C (O) NHCH₂CH = NOMe
CF_Three          Cl C (O) NHCH₂(Me) = NOMe
CF_Three          Cl C (O) NHCH₂CN
CF_Three          Cl C (O) NHCH₂C (O) OH
CF_Three          Cl C (O) NHCH₂C (O) OMe
CF_Three          Cl C (O) NHCH₂C (O) OEt
CF_Three          Cl C (O) NHCH₂C (O) OCH₂CF_Three
CF_Three          Cl C (O) NHCH₂C (O) NH₂
CF_Three          Cl C (O) NHCH₂C (O) NHMe
CF_Three          Cl C (O) NHCH₂C (O) NMe₂
CF_Three          Cl C (O) NHCH₂C (O) NHEt
CF_Three          Cl C (O) NHCH₂C (O) NHCH₂CH₂Cl
CF_Three          Cl C (O) NHCH₂C (O) NHCH₂CH₂Br
CF_Three          Cl C (O) NHCH₂C (O) NHCH₂CH₂F
CF_Three          Cl C (O) NHCH₂C (O) NHCH₂CF_Three
CF_Three          Cl C (O) NHCH₂C (O) N (Me) CH₂CF_Three
CF_Three          Cl C (O) N (Me) CH₂C (O) NHCH₂CF_Three
CF_Three          Cl C (O) NHCH₂C (O) NHCH₂CH₂OH
CF_Three          Cl C (O) NHCH (Me) C (O) OH
CF_Three          Cl C (O) NHCH (Me) C (O) OMe
CF_Three          Cl C (O) NHCH (Me) C (O) NHCH₂CH₂Cl
CF_Three          Cl C (O) NHCH (Me) C (O) NHCH₂CF_Three
CF_Three          Cl C (O) NHCH₂Ph
CF_Three          Cl C (O) NHCH₂(Ph-4-F)
CF_Three          Cl C (O) NHCH (Me) (Ph-4-F)
CF_Three          Cl C (O) NHCH (Et) (Ph-4-F)
CF_Three          Cl C (O) NHCH (CH₂CN) (Ph-4-F)
CF_Three          Cl C (O) NHCH (CH₂OMe) (Ph-4-F)
CF_Three          Cl C (O) NHCH [C (O) Me] (Ph-4-F)
CF_Three          Cl C (O) NHCH [C (O) OMe] (Ph-4-F)
CF_Three          Cl C (O) NHCH (Ph-4-CN)
CF_Three          Cl C (O) NHCH₂CH₂Cl
CF_Three          Cl C (O) NHCH₂-(2-pyridyl)
CF_Three          Cl C (O) NHCH₂-(4-thiazolyl)
CF_Three          Cl C (O) NHCH₂-(1,3-dioxolane-2-yl)
CF_Three          Cl C (O) NHCH₂CH₂SMe
CF_Three          Cl C (O) NHCH (Me) CH₂SMe
CF_Three          Cl C (O) NHCH₂CH₂CH₂SMe
CF_Three          Cl C (O) NHCH₂CH₂S (O) Me
CF_Three          Cl C (O) NHCH (Me) CH₂S (O) Me
CF_Three          Cl C (O) NHCH₂CH₂CH₂S (O) Me
CF_Three          Cl C (O) NHCH₂CH₂S (O)₂Me
CF_Three          Cl C (O) NHCH (Me) CH₂S (O)₂Me
CF_Three          Cl C (O) NHCH₂CH₂CH₂S (O)₂Me
CF_Three          Cl C (O) NHNH₂
CF_Three          Cl C (O) NHNHMe
CF_Three          Cl C (O) NHNMe₂
CF_Three          Cl C (O) NHNHPh
CF_Three          Cl C (O) NHC (O) OMe
CF_Three          Cl C (O) NHC (O) OEt
CF_Three          Cl C (O) NHC (O) NHMe
CF_Three          Cl C (O) NHC (O) NHEt
CF_Three          Cl C (O) NHC (O) NH₂
CF_Three          Cl C (O) NHC (O) NMe₂
CF_Three          Cl C (O) NHPh
CF_Three          Cl C (O) NH (Ph-4-Cl)
CF_Three          Cl C (O) NH (2-pyridyl)
CF_Three          Cl C (O) NHCH₂C (O) NH-i-Pr
CF_Three          Cl C (O) NHCH₂C (O) NHCH₂-i-Pr
CF_Three          Cl C (O) NHCH (Me) C (O) NHCH₂-i-Pr
CF_Three          Cl C (O) NHCH (Me) C (O) NHCH₂CH₂F
CF_Three          Cl D-11a
CF_Three          Cl D-11b
CF_Three          Cl D-21a
CF_Three          Cl D-35a
CF_Three          Cl D-36a
CF_Three          Cl D-37a
CF_Three          Cl D-38a
CF_Three          Cl D-39a
CF_Three          Cl D-40a
CF_Three          Cl D-41a
CF_Three          Me F
CF_Three          Me Cl
CF_Three          Me Br
CF_Three          Me I
CF_Three          Me CN
CF_Three          Me OH
CF_Three          Me OMe
CF_Three          Me OCH₂Ph
CF_Three          Me OS (O)₂Me
CF_Three          Me OS (O)₂CF_Three
CF_Three          Me OS (O)₂(Ph-4-Me)
CF_Three          Me S (O)₂Me
CF_Three          Me S (O)₂CF_Three
CF_Three          Me NO₂
CF_Three          Me NH₂
CF_Three          Me NHC (O) Me
CF_Three          Me NHC (O) OMe
CF_Three          Me NHC (O) OEt
CF_Three          Me Me
CF_Three          Me Et
CF_Three          Me n-Pr
CF_Three          Me CH₂Cl
CF_Three          Me CH₂Br
CF_Three          Me CH₂OH
CF_Three          Me CH₂NH₂
CF_Three          Me CH₂NHC (O) Me
CF_Three          Me CH₂NHC (O) Et
CF_Three          Me CH₂NHC (O) -n-Pr
CF_Three          Me CH₂NHC (O) -c-Pr
CF_Three          Me CH₂NHC (O) CH₂SMe
CF_Three          Me CH₂NHC (O) CH₂S (O)₂Me
CF_Three          Me CH₂NHC (O) CH₂SEt
CF_Three          Me CH₂NHC (O) CH₂S (O)₂Et
CF_Three          Me CH₂NHC (O) CH₂S-n-Pr
CF_Three          Me CH₂NHC (O) CH₂S (O)₂-NPR
CF_Three          Me CH₂NHC (O) CH₂S-c-Pr
CF_Three          Me CH₂NHC (O) CH₂S (O)₂-c-Pr
CF_Three          Me CH₂NHC (O) OMe
CF_Three          Me CH₂NHC (O) OEt
CF_Three          Me CH₂NHC (O) O-n-Pr
CF_Three          Me CH₂NHC (O) O-c-Pr
CF_Three          Me CH₂NHC (O) NHMe
CF_Three          Me CH₂NHC (O) NHEt
CF_Three          Me CH₂NHC (O) NH-n-Pr
CF_Three          Me CH₂NHC (O) NH-c-Pr
CF_Three          Me CH₂NO₂
CF_Three          Me CH₂-(G-1)
CF_Three          Me CH₂-(G-2)
CF_Three          Me C (O) OH
CF_Three          Me C (O) OMe
CF_Three          Me C (O) OEt
CF_Three          Me C (O) O-n-Pr
CF_Three          Me C (O) NH₂
CF_Three          Me C (O) NHMe
CF_Three          Me C (O) NHEt
CF_Three          Me C (O) NH-n-Pr
CF_Three          Me C (O) NH-c-Pr
CF_Three          Me C (O) NHCH₂-c-Pr
CF_Three          Me C (O) NHCH₂CF_Three
CF_Three          Me C (O) NH (Me) CH₂CF_Three
CF_Three          Me C (O) NH (CH₂OMe) CH₂CF_Three
CF_Three          Me C (O) NH [C (O) OMe] CH₂CF_Three
CF_Three          Me C (O) NHCH₂CH = CH₂
CF_Three          Me C (O) NHCH₂CH₂CH₂OMe
CF_Three          Me C (O) NHCH = NOMe
CF_Three          Me C (O) NHCH = NOEt
CF_Three          Me C (O) NHC (Me) = NOMe
CF_Three          Me C (O) NHC (Me) = NOEt
CF_Three          Me C (O) NHCH₂CH = NOH
CF_Three          Me C (O) NHCH₂CH = NOMe
CF_Three          Me C (O) NHCH₂(Me) = NOMe
CF_Three          Me C (O) NHCH₂CN
CF_Three          Me C (O) NHCH₂C (O) OH
CF_Three          Me C (O) NHCH₂C (O) OMe
CF_Three          Me C (O) NHCH₂C (O) OEt
CF_Three          Me C (O) NHCH₂C (O) OCH₂CF_Three
CF_Three          Me C (O) NHCH₂C (O) NH₂
CF_Three          Me C (O) NHCH₂C (O) NHMe
CF_Three          Me C (O) NHCH₂C (O) NMe₂
CF_Three          Me C (O) NHCH₂C (O) NHEt
CF_Three          Me C (O) NHCH₂C (O) NHCH₂CH₂Cl
CF_Three          Me C (O) NHCH₂C (O) NHCH₂CH₂Br
CF_Three          Me C (O) NHCH₂C (O) NHCH₂CH₂F
CF_Three          Me C (O) NHCH₂C (O) NHCH₂CF_Three
CF_Three          Me C (O) NHCH₂C (O) N (Me) CH₂CF_Three
CF_Three          Me C (O) N (Me) CH₂C (O) NHCH₂CF_Three
CF_Three          Me C (O) NHCH₂C (O) NHCH₂CH₂OH
CF_Three          Me C (O) NHCH (Me) C (O) OH
CF_Three          Me C (O) NHCH (Me) C (O) OMe
CF_Three          Me C (O) NHCH (Me) C (O) NHCH₂CH₂Cl
CF_Three          Me C (O) NHCH (Me) C (O) NHCH₂CF_Three
CF_Three          Me C (O) NHCH₂Ph
CF_Three          Me C (O) NHCH₂(Ph-4-F)
CF_Three          Me C (O) NHCH (Me) (Ph-4-F)
CF_Three          Me C (O) NHCH (Et) (Ph-4-F)
CF_Three          Me C (O) NHCH (CH₂CN) (Ph-4-F)
CF_Three          Me C (O) NHCH (CH₂OMe) (Ph-4-F)
CF_Three          Me C (O) NHCH [C (O) Me] (Ph-4-F)
CF_Three          Me C (O) NHCH [C (O) OMe] (Ph-4-F)
CF_Three          Me C (O) NHCH (Ph-4-CN)
CF_Three          Me C (O) NHCH₂CH₂Cl
CF_Three          Me C (O) NHCH₂-(2-pyridyl)
CF_Three          Me C (O) NHCH₂-(4-thiazolyl)
CF_Three          Me C (O) NHCH₂-(1,3-dioxolane-2-yl)
CF_Three          Me C (O) NHCH₂CH₂SMe
CF_Three          Me C (O) NHCH (Me) CH₂SMe
CF_Three          Me C (O) NHCH₂CH₂CH₂SMe
CF_Three          Me C (O) NHCH₂CH₂S (O) Me
CF_Three          Me C (O) NHCH (Me) CH₂S (O) Me
CF_Three          Me C (O) NHCH₂CH₂CH₂S (O) Me
CF_Three          Me C (O) NHCH₂CH₂S (O)₂Me
CF_Three          Me C (O) NHCH (Me) CH₂S (O)₂Me
CF_Three          Me C (O) NHCH₂CH₂CH₂S (O)₂Me
CF_Three          Me C (O) NHNH₂
CF_Three          Me C (O) NHNHMe
CF_Three          Me C (O) NHNMe₂
CF_Three          Me C (O) NHNHPh
CF_Three          Me C (O) NHC (O) OMe
CF_Three          Me C (O) NHC (O) OEt
CF_Three          Me C (O) NHC (O) NHMe
CF_Three          Me C (O) NHC (O) NHEt
CF_Three          Me C (O) NHC (O) NH₂
CF_Three          Me C (O) NHC (O) NMe₂
CF_Three          Me C (O) NHPh
CF_Three          Me C (O) NH (Ph-4-Cl)
CF_Three          Me C (O) NH (2-pyridyl)
CF_Three          Me C (O) NHCH₂C (O) NH-i-Pr
CF_Three          Me C (O) NHCH₂C (O) NHCH₂-i-Pr
CF_Three          Me C (O) NHCH (Me) C (O) NHCH₂-i-Pr
CF_Three          Me C (O) NHCH (Me) C (O) NHCH₂CH₂F
CF_Three          Me D-11a
CF_Three          Me D-11b
CF_Three          Me D-21a
CF_Three          Me D-35a
CF_Three          Me D-36a
CF_Three          Me D-37a
CF_Three          Me D-38a
CF_Three          Me D-39a
CF_Three          Me D-40a
CF_Three          Me D-41a
CF_Three          CF_Three         F
CF_Three          CF_Three         Cl
CF_Three          CF_Three         Br
CF_Three          CF_Three         I
CF_Three          CF_Three         CN
CF_Three          CF_Three         OH
CF_Three          CF_Three         OMe
CF_Three          CF_Three         OCH₂Ph
CF_Three          CF_Three         OS (O)₂Me
CF_Three          CF_Three         OS (O)₂CF_Three
CF_Three          CF_Three         OS (O)₂(Ph-4-Me)
CF_Three          CF_Three         S (O)₂Me
CF_Three          CF_Three         S (O)₂CF_Three
CF_Three          CF_Three         NO₂
CF_Three          CF_Three         NH₂
CF_Three          CF_Three         NHC (O) Me
CF_Three          CF_Three         NHC (O) OMe
CF_Three          CF_Three         NHC (O) OEt
CF_Three          CF_Three         Me
CF_Three          CF_Three         Et
CF_Three          CF_Three         NPR
CF_Three          CF_Three         CH₂Cl
CF_Three          CF_Three         CH₂Br
CF_Three          CF_Three         CH₂OH
CF_Three          CF_Three         CH₂NH₂
CF_Three          CF_Three         CH₂NHC (O) Me
CF_Three          CF_Three         CH₂NHC (O) Et
CF_Three          CF_Three         CH₂NHC (O) -n-Pr
CF_Three          CF_Three         CH₂NHC (O) -c-Pr
CF_Three          CF_Three         CH₂NHC (O) CH₂SMe
CF_Three          CF_Three         CH₂NHC (O) CH₂S (O)₂Me
CF_Three          CF_Three         CH₂NHC (O) CH₂SEt
CF_Three          CF_Three         CH₂NHC (O) CH₂S (O)₂Et
CF_Three          CF_Three         CH₂NHC (O) CH₂S-n-Pr
CF_Three          CF_Three         CH₂NHC (O) CH₂S (O)₂-NPR
CF_Three          CF_Three         CH₂NHC (O) CH₂S-c-Pr
CF_Three          CF_Three         CH₂NHC (O) CH₂S (O)₂-c-Pr
CF_Three          CF_Three         CH₂NHC (O) OMe
CF_Three          CF_Three         CH₂NHC (O) OEt
CF_Three          CF_Three         CH₂NHC (O) O-n-Pr
CF_Three          CF_Three         CH₂NHC (O) O-c-Pr
CF_Three          CF_Three         CH₂NHC (O) NHMe
CF_Three          CF_Three         CH₂NHC (O) NHEt
CF_Three          CF_Three         CH₂NHC (O) NH-n-Pr
CF_Three          CF_Three         CH₂NHC (O) NH-c-Pr
CF_Three          CF_Three         CH₂NO₂
CF_Three          CF_Three         CH₂-(G-1)
CF_Three          CF_Three         CH₂-(G-2)
CF_Three          CF_Three         C (O) OH
CF_Three          CF_Three         C (O) OMe
CF_Three          CF_Three         C (O) OEt
CF_Three          CF_Three         C (O) O-n-Pr
CF_Three          CF_Three         C (O) NH₂
CF_Three          CF_Three         C (O) NHMe
CF_Three          CF_Three         C (O) NHEt
CF_Three          CF_Three         C (O) NH-n-Pr
CF_Three          CF_Three         C (O) NH-c-Pr
CF_Three          CF_Three         C (O) NHCH₂-c-Pr
CF_Three          CF_Three         C (O) NHCH₂CF_Three
CF_Three          CF_Three         C (O) NH (Me) CH₂CF_Three
CF_Three          CF_Three         C (O) NH (CH₂OMe) CH₂CF_Three
CF_Three          CF_Three         C (O) NH [C (O) OMe] CH₂CF_Three
CF_Three          CF_Three         C (O) NHCH₂CH = CH₂
CF_Three          CF_Three         C (O) NHCH₂CH₂CH₂OMe
CF_Three          CF_Three         C (O) NHCH = NOMe
CF_Three          CF_Three         C (O) NHCH = NOEt
CF_Three          CF_Three         C (O) NHC (Me) = NOMe
CF_Three          CF_Three         C (O) NHC (Me) = NOEt
CF_Three          CF_Three         C (O) NHCH₂CH = NOH
CF_Three          CF_Three         C (O) NHCH₂CH = NOMe
CF_Three          CF_Three         C (O) NHCH₂(Me) = NOMe
CF_Three          CF_Three         C (O) NHCH₂CN
CF_Three          CF_Three         C (O) NHCH₂C (O) OH
CF_Three          CF_Three         C (O) NHCH₂C (O) OMe
CF_Three          CF_Three         C (O) NHCH₂C (O) OEt
CF_Three          CF_Three         C (O) NHCH₂C (O) OCH₂CF_Three
CF_Three          CF_Three         C (O) NHCH₂C (O) NH₂
CF_Three          CF_Three         C (O) NHCH₂C (O) NHMe
CF_Three          CF_Three         C (O) NHCH₂C (O) NMe₂
CF_Three          CF_Three         C (O) NHCH₂C (O) NHEt
CF_Three          CF_Three         C (O) NHCH₂C (O) NHCH₂CH₂Cl
CF_Three          CF_Three         C (O) NHCH₂C (O) NHCH₂CH₂Br
CF_Three          CF_Three         C (O) NHCH₂C (O) NHCH₂CH₂F
CF_Three          CF_Three         C (O) NHCH₂C (O) NHCH₂CF_Three
CF_Three          CF_Three         C (O) NHCH₂C (O) N (Me) CH₂CF_Three
CF_Three          CF_Three         C (O) N (Me) CH₂C (O) NHCH₂CF_Three
CF_Three          CF_Three         C (O) NHCH₂C (O) NHCH₂CH₂OH
CF_Three          CF_Three         C (O) NHCH (Me) C (O) OH
CF_Three          CF_Three         C (O) NHCH (Me) C (O) OMe
CF_Three          CF_Three         C (O) NHCH (Me) C (O) NHCH₂CH₂Cl
CF_Three          CF_Three         C (O) NHCH (Me) C (O) NHCH₂CF_Three
CF_Three          CF_Three         C (O) NHCH₂Ph
CF_Three          CF_Three         C (O) NHCH₂(Ph-4-F)
CF_Three          CF_Three         C (O) NHCH (Me) (Ph-4-F)
CF_Three          CF_Three         C (O) NHCH (Et) (Ph-4-F)
CF_Three          CF_Three         C (O) NHCH (CH₂CN) (Ph-4-F)
CF_Three          CF_Three         C (O) NHCH (CH₂OMe) (Ph-4-F)
CF_Three          CF_Three         C (O) NHCH [C (O) Me] (Ph-4-F)
CF_Three          CF_Three         C (O) NHCH [C (O) OMe] (Ph-4-F)
CF_Three          CF_Three         C (O) NHCH (Ph-4-CN)
CF_Three          CF_Three         C (O) NHCH₂CH₂Cl
CF_Three          CF_Three         C (O) NHCH₂-(2-pyridyl)
CF_Three          CF_Three         C (O) NHCH₂-(4-thiazolyl)
CF_Three          CF_Three         C (O) NHCH₂-(1,3-dioxolane-2-yl)
CF_Three          CF_Three         C (O) NHCH₂CH₂SMe
CF_Three          CF_Three         C (O) NHCH (Me) CH₂SMe
CF_Three          CF_Three         C (O) NHCH₂CH₂CH₂SMe
CF_Three          CF_Three         C (O) NHCH₂CH₂S (O) Me
CF_Three          CF_Three         C (O) NHCH (Me) CH₂S (O) Me
CF_Three          CF_Three         C (O) NHCH₂CH₂CH₂S (O) Me
CF_Three          CF_Three         C (O) NHCH₂CH₂S (O)₂Me
CF_Three          CF_Three         C (O) NHCH (Me) CH₂S (O)₂Me
CF_Three          CF_Three         C (O) NHCH₂CH₂CH₂S (O)₂Me
CF_Three          CF_Three         C (O) NHNH₂
CF_Three          CF_Three         C (O) NHNHMe
CF_Three          CF_Three         C (O) NHNMe₂
CF_Three          CF_Three         C (O) NHNHPh
CF_Three          CF_Three         C (O) NHC (O) OMe
CF_Three          CF_Three         C (O) NHC (O) OEt
CF_Three          CF_Three         C (O) NHC (O) NHMe
CF_Three          CF_Three         C (O) NHC (O) NHEt
CF_Three          CF_Three         C (O) NHC (O) NH₂
CF_Three          CF_Three         C (O) NHC (O) NMe₂
CF_Three          CF_Three         C (O) NHPh
CF_Three          CF_Three         C (O) NH (Ph-4-Cl)
CF_Three          CF_Three         C (O) NH (2-pyridyl)
CF_Three          CF_Three         C (O) NHCH₂C (O) NH-i-Pr
CF_Three          CF_Three         C (O) NHCH₂C (O) NHCH₂-i-Pr
CF_Three          CF_Three         C (O) NHCH (Me) C (O) NHCH₂-i-Pr
CF_Three          CF_Three         C (O) NHCH (Me) C (O) NHCH₂CH₂F
CF_Three          CF_Three         D-11a
CF_Three          CF_Three         D-11b
CF_Three          CF_Three         D-21a
CF_Three          CF_Three         D-35a
CF_Three          CF_Three         D-36a
CF_Three          CF_Three         D-37a
CF_Three          CF_Three         D-38a
CF_Three          CF_Three         D-39a
CF_Three          CF_Three         D-40a
CF_Three          CF_Three         D-41a
CF_Three          NO₂         F
CF_Three          NO₂         Cl
CF_Three          NO₂         Br
CF_Three          NO₂         I
CF_Three          NO₂         CN
CF_Three          NO₂         OH
CF_Three          NO₂         OMe
CF_Three          NO₂         OCH₂Ph
CF_Three          NO₂         OS (O)₂Me
CF_Three          NO₂         OS (O)₂CF_Three
CF_Three          NO₂         OS (O)₂(Ph-4-Me)
CF_Three          NO₂         S (O)₂Me
CF_Three          NO₂         S (O)₂CF_Three
CF_Three          NO₂         NO₂
CF_Three          NO₂         NH₂
CF_Three          NO₂         NHC (O) Me
CF_Three          NO₂         NHC (O) OMe
CF_Three          NO₂         NHC (O) OEt
CF_Three          NO₂         Me
CF_Three          NO₂         Et
CF_Three          NO₂         NPR
CF_Three          NO₂         CH₂Cl
CF_Three          NO₂         CH₂Br
CF_Three          NO₂         CH₂OH
CF_Three          NO₂         CH₂NH₂
CF_Three          NO₂         CH₂NHC (O) Me
CF_Three          NO₂         CH₂NHC (O) Et
CF_Three          NO₂         CH₂NHC (O) -n-Pr
CF_Three          NO₂         CH₂NHC (O) -c-Pr
CF_Three          NO₂         CH₂NHC (O) CH₂SMe
CF_Three          NO₂         CH₂NHC (O) CH₂S (O)₂Me
CF_Three          NO₂         CH₂NHC (O) CH₂SEt
CF_Three          NO₂         CH₂NHC (O) CH₂S (O)₂Et
CF_Three          NO₂         CH₂NHC (O) CH₂S-n-Pr
CF_Three          NO₂         CH₂NHC (O) CH₂S (O)₂-NPR
CF_Three          NO₂         CH₂NHC (O) CH₂S-c-Pr
CF_Three          NO₂         CH₂NHC (O) CH₂S (O)₂-c-Pr
CF_Three          NO₂         CH₂NHC (O) OMe
CF_Three          NO₂         CH₂NHC (O) OEt
CF_Three          NO₂         CH₂NHC (O) O-n-Pr
CF_Three          NO₂         CH₂NHC (O) O-c-Pr
CF_Three          NO₂         CH₂NHC (O) NHMe
CF_Three          NO₂         CH₂NHC (O) NHEt
CF_Three          NO₂         CH₂NHC (O) NH-n-Pr
CF_Three          NO₂         CH₂NHC (O) NH-c-Pr
CF_Three          NO₂         CH₂NO₂
CF_Three          NO₂         CH₂-(G-1)
CF_Three          NO₂         CH₂-(G-2)
CF_Three          NO₂         C (O) OH
CF_Three          NO₂         C (O) OMe
CF_Three          NO₂         C (O) OEt
CF_Three          NO₂         C (O) O-n-Pr
CF_Three          NO₂         C (O) NH₂
CF_Three          NO₂         C (O) NHMe
CF_Three          NO₂         C (O) NHEt
CF_Three          NO₂         C (O) NH-n-Pr
CF_Three          NO₂         C (O) NH-c-Pr
CF_Three          NO₂         C (O) NHCH₂-c-Pr
CF_Three          NO₂         C (O) NHCH₂CF_Three
CF_Three          NO₂         C (O) NH (Me) CH₂CF_Three
CF_Three          NO₂         C (O) NH (CH₂OMe) CH₂CF_Three
CF_Three          NO₂         C (O) NH [C (O) OMe] CH₂CF_Three
CF_Three          NO₂         C (O) NHCH₂CH = CH₂
CF_Three          NO₂         C (O) NHCH₂CH₂CH₂OMe
CF_Three          NO₂         C (O) NHCH = NOMe
CF_Three          NO₂         C (O) NHCH = NOEt
CF_Three          NO₂         C (O) NHC (Me) = NOMe
CF_Three          NO₂         C (O) NHC (Me) = NOEt
CF_Three          NO₂         C (O) NHCH₂CH = NOH
CF_Three          NO₂         C (O) NHCH₂CH = NOMe
CF_Three          NO₂         C (O) NHCH₂(Me) = NOMe
CF_Three          NO₂         C (O) NHCH₂CN
CF_Three          NO₂         C (O) NHCH₂C (O) OH
CF_Three          NO₂         C (O) NHCH₂C (O) OMe
CF_Three          NO₂         C (O) NHCH₂C (O) OEt
CF_Three          NO₂         C (O) NHCH₂C (O) OCH₂CF_Three
CF_Three          NO₂         C (O) NHCH₂C (O) NH₂
CF_Three          NO₂         C (O) NHCH₂C (O) NHMe
CF_Three          NO₂         C (O) NHCH₂C (O) NMe₂
CF_Three          NO₂         C (O) NHCH₂C (O) NHEt
CF_Three          NO₂         C (O) NHCH₂C (O) NHCH₂CH₂Cl
CF_Three          NO₂         C (O) NHCH₂C (O) NHCH₂CH₂Br
CF_Three          NO₂         C (O) NHCH₂C (O) NHCH₂CH₂F
CF_Three          NO₂         C (O) NHCH₂C (O) NHCH₂CF_Three
CF_Three          NO₂         C (O) NHCH₂C (O) N (Me) CH₂CF_Three
CF_Three          NO₂         C (O) N (Me) CH₂C (O) NHCH₂CF_Three
CF_Three          NO₂         C (O) NHCH₂C (O) NHCH₂CH₂OH
CF_Three          NO₂         C (O) NHCH (Me) C (O) OH
CF_Three          NO₂         C (O) NHCH (Me) C (O) OMe
CF_Three          NO₂         C (O) NHCH (Me) C (O) NHCH₂CH₂Cl
CF_Three          NO₂         C (O) NHCH (Me) C (O) NHCH₂CF_Three
CF_Three          NO₂         C (O) NHCH₂Ph
CF_Three          NO₂         C (O) NHCH₂(Ph-4-F)
CF_Three          NO₂         C (O) NHCH (Me) (Ph-4-F)
CF_Three          NO₂         C (O) NHCH (Et) (Ph-4-F)
CF_Three          NO₂         C (O) NHCH (CH₂CN) (Ph-4-F)
CF_Three          NO₂         C (O) NHCH (CH₂OMe) (Ph-4-F)
CF_Three          NO₂         C (O) NHCH [C (O) Me] (Ph-4-F)
CF_Three          NO₂         C (O) NHCH [C (O) OMe] (Ph-4-F)
CF_Three          NO₂         C (O) NHCH (Ph-4-CN)
CF_Three          NO₂         C (O) NHCH₂CH₂Cl
CF_Three          NO₂         C (O) NHCH₂-(2-pyridyl)
CF_Three          NO₂         C (O) NHCH₂-(4-thiazolyl)
CF_Three          NO₂         C (O) NHCH₂-(1,3-dioxolane-2-yl)
CF_Three          NO₂         C (O) NHCH₂CH₂SMe
CF_Three          NO₂         C (O) NHCH (Me) CH₂SMe
CF_Three          NO₂         C (O) NHCH₂CH₂CH₂SMe
CF_Three          NO₂         C (O) NHCH₂CH₂S (O) Me
CF_Three          NO₂         C (O) NHCH (Me) CH₂S (O) Me
CF_Three          NO₂         C (O) NHCH₂CH₂CH₂S (O) Me
CF_Three          NO₂         C (O) NHCH₂CH₂S (O)₂Me
CF_Three          NO₂         C (O) NHCH (Me) CH₂S (O)₂Me
CF_Three          NO₂         C (O) NHCH₂CH₂CH₂S (O)₂Me
CF_Three          NO₂         C (O) NHNH₂
CF_Three          NO₂         C (O) NHNHMe
CF_Three          NO₂         C (O) NHNMe₂
CF_Three          NO₂         C (O) NHNHPh
CF_Three          NO₂         C (O) NHC (O) OMe
CF_Three          NO₂         C (O) NHC (O) OEt
CF_Three          NO₂         C (O) NHC (O) NHMe
CF_Three          NO₂         C (O) NHC (O) NHEt
CF_Three          NO₂         C (O) NHC (O) NH₂
CF_Three          NO₂         C (O) NHC (O) NMe₂
CF_Three          NO₂         C (O) NHPh
CF_Three          NO₂         C (O) NH (Ph-4-Cl)
CF_Three          NO₂         C (O) NH (2-pyridyl)
CF_Three          NO₂         C (O) NHCH₂C (O) NH-i-Pr
CF_Three          NO₂         C (O) NHCH₂C (O) NHCH₂-i-Pr
CF_Three          NO₂         C (O) NHCH (Me) C (O) NHCH₂-i-Pr
CF_Three          NO₂         C (O) NHCH (Me) C (O) NHCH₂CH₂F
CF_Three          NO₂         D-11a
CF_Three          NO₂         D-11b
CF_Three          NO₂         D-21a
CF_Three          NO₂         D-35a
CF_Three          NO₂         D-36a
CF_Three          NO₂         D-37a
CF_Three          NO₂         D-38a
CF_Three          NO₂         D-39a
CF_Three          NO₂         D-40a
CF_Three          NO₂         D-41a
CF_Three          CN F
CF_Three          CN Cl
CF_Three          CN Br
CF_Three          CN I
CF_Three          CN CN
CF_Three          CN OH
CF_Three          CN OMe
CF_Three          CN OCH₂Ph
CF_Three          CN OS (O)₂Me
CF_Three          CN OS (O)₂CF_Three
CF_Three          CN OS (O)₂(Ph-4-Me)
CF_Three          CN S (O)₂Me
CF_Three          CN S (O)₂CF_Three
CF_Three          CN NO₂
CF_Three          CN NH₂
CF_Three          CN NHC (O) Me
CF_Three          CN NHC (O) OMe
CF_Three          CN NHC (O) OEt
CF_Three          CN Me
CF_Three          CN Et
CF_Three          CN n-Pr
CF_Three          CN CH₂Cl
CF_Three          CN CH₂Br
CF_Three          CN CH₂OH
CF_Three          CN CH₂NH₂
CF_Three          CN CH₂NHC (O) Me
CF_Three          CN CH₂NHC (O) Et
CF_Three          CN CH₂NHC (O) -n-Pr
CF_Three          CN CH₂NHC (O) -c-Pr
CF_Three          CN CH₂NHC (O) CH₂SMe
CF_Three          CN CH₂NHC (O) CH₂S (O)₂Me
CF_Three          CN CH₂NHC (O) CH₂SEt
CF_Three          CN CH₂NHC (O) CH₂S (O)₂Et
CF_Three          CN CH₂NHC (O) CH₂S-n-Pr
CF_Three          CN CH₂NHC (O) CH₂S (O)₂-NPR
CF_Three          CN CH₂NHC (O) CH₂S-c-Pr
CF_Three          CN CH₂NHC (O) CH₂S (O)₂-c-Pr
CF_Three          CN CH₂NHC (O) OMe
CF_Three          CN CH₂NHC (O) OEt
CF_Three          CN CH₂NHC (O) O-n-Pr
CF_Three          CN CH₂NHC (O) O-c-Pr
CF_Three          CN CH₂NHC (O) NHMe
CF_Three          CN CH₂NHC (O) NHEt
CF_Three          CN CH₂NHC (O) NH-n-Pr
CF_Three          CN CH₂NHC (O) NH-c-Pr
CF_Three          CN CH₂NO₂
CF_Three          CN CH₂-(G-1)
CF_Three          CN CH₂-(G-2)
CF_Three          CN C (O) OH
CF_Three          CN C (O) OMe
CF_Three          CN C (O) OEt
CF_Three          CN C (O) O-n-Pr
CF_Three          CN C (O) NH₂
CF_Three          CN C (O) NHMe
CF_Three          CN C (O) NHEt
CF_Three          CN C (O) NH-n-Pr
CF_Three          CN C (O) NH-c-Pr
CF_Three          CN C (O) NHCH₂-c-Pr
CF_Three          CN C (O) NHCH₂CF_Three
CF_Three          CN C (O) NH (Me) CH₂CF_Three
CF_Three          CN C (O) NH (CH₂OMe) CH₂CF_Three
CF_Three          CN C (O) NH [C (O) OMe] CH₂CF_Three
CF_Three          CN C (O) NHCH₂CH = CH₂
CF_Three          CN C (O) NHCH₂CH₂CH₂OMe
CF_Three          CN C (O) NHCH = NOMe
CF_Three          CN C (O) NHCH = NOEt
CF_Three          CN C (O) NHC (Me) = NOMe
CF_Three          CN C (O) NHC (Me) = NOEt
CF_Three          CN C (O) NHCH₂CH = NOH
CF_Three          CN C (O) NHCH₂CH = NOMe
CF_Three          CN C (O) NHCH₂(Me) = NOMe
CF_Three          CN C (O) NHCH₂CN
CF_Three          CN C (O) NHCH₂C (O) OH
CF_Three          CN C (O) NHCH₂C (O) OMe
CF_Three          CN C (O) NHCH₂C (O) OEt
CF_Three          CN C (O) NHCH₂C (O) OCH₂CF_Three
CF_Three          CN C (O) NHCH₂C (O) NH₂
CF_Three          CN C (O) NHCH₂C (O) NHMe
CF_Three          CN C (O) NHCH₂C (O) NMe₂
CF_Three          CN C (O) NHCH₂C (O) NHEt
CF_Three          CN C (O) NHCH₂C (O) NHCH₂CH₂Cl
CF_Three          CN C (O) NHCH₂C (O) NHCH₂CH₂Br
CF_Three          CN C (O) NHCH₂C (O) NHCH₂CH₂F
CF_Three          CN C (O) NHCH₂C (O) NHCH₂CF_Three
CF_Three          CN C (O) NHCH₂C (O) N (Me) CH₂CF_Three
CF_Three          CN C (O) N (Me) CH₂C (O) NHCH₂CF_Three
CF_Three          CN C (O) NHCH₂C (O) NHCH₂CH₂OH
CF_Three          CN C (O) NHCH (Me) C (O) OH
CF_Three          CN C (O) NHCH (Me) C (O) OMe
CF_Three          CN C (O) NHCH (Me) C (O) NHCH₂CH₂Cl
CF_Three          CN C (O) NHCH (Me) C (O) NHCH₂CF_Three
CF_Three          CN C (O) NHCH₂Ph
CF_Three          CN C (O) NHCH₂(Ph-4-F)
CF_Three          CN C (O) NHCH (Me) (Ph-4-F)
CF_Three          CN C (O) NHCH (Et) (Ph-4-F)
CF_Three          CN C (O) NHCH (CH₂CN) (Ph-4-F)
CF_Three          CN C (O) NHCH (CH₂OMe) (Ph-4-F)
CF_Three          CN C (O) NHCH [C (O) Me] (Ph-4-F)
CF_Three          CN C (O) NHCH [C (O) OMe] (Ph-4-F)
CF_Three          CN C (O) NHCH (Ph-4-CN)
CF_Three          CN C (O) NHCH₂CH₂Cl
CF_Three          CN C (O) NHCH₂-(2-pyridyl)
CF_Three          CN C (O) NHCH₂-(4-thiazolyl)
CF_Three          CN C (O) NHCH₂-(1,3-dioxolane-2-yl)
CF_Three          CN C (O) NHCH₂CH₂SMe
CF_Three          CN C (O) NHCH (Me) CH₂SMe
CF_Three          CN C (O) NHCH₂CH₂CH₂SMe
CF_Three          CN C (O) NHCH₂CH₂S (O) Me
CF_Three          CN C (O) NHCH (Me) CH₂S (O) Me
CF_Three          CN C (O) NHCH₂CH₂CH₂S (O) Me
CF_Three          CN C (O) NHCH₂CH₂S (O)₂Me
CF_Three          CN C (O) NHCH (Me) CH₂S (O)₂Me
CF_Three          CN C (O) NHCH₂CH₂CH₂S (O)₂Me
CF_Three          CN C (O) NHNH₂
CF_Three          CN C (O) NHNHMe
CF_Three          CN C (O) NHNMe₂
CF_Three          CN C (O) NHNHPh
CF_Three          CN C (O) NHC (O) OMe
CF_Three          CN C (O) NHC (O) OEt
CF_Three          CN C (O) NHC (O) NHMe
CF_Three          CN C (O) NHC (O) NHEt
CF_Three          CN C (O) NHC (O) NH₂
CF_Three          CN C (O) NHC (O) NMe₂
CF_Three          CN C (O) NHPh
CF_Three          CN C (O) NH (Ph-4-Cl)
CF_Three          CN C (O) NH (2-pyridyl)
CF_Three          CN C (O) NHCH₂C (O) NH-i-Pr
CF_Three          CN C (O) NHCH₂C (O) NHCH₂-i-Pr
CF_Three          CN C (O) NHCH (Me) C (O) NHCH₂-i-Pr
CF_Three          CN C (O) NHCH (Me) C (O) NHCH₂CH₂F
CF_Three          CN D-11a
CF_Three          CN D-11b
CF_Three          CN D-21a
CF_Three          CN D-35a
CF_Three          CN D-36a
CF_Three          CN D-37a
CF_Three          CN D-38a
CF_Three          CN D-39a
CF_Three          CN D-40a
CF_Three          CN D-41a
CF₂Cl H F
CF₂Cl H Cl
CF₂Cl H Br
CF₂Cl H I
CF₂Cl H CN
CF₂Cl H OH
CF₂Cl H OMe
CF₂Cl H OCH₂Ph
CF₂Cl H OS (O)₂Me
CF₂Cl H OS (O)₂CF_Three
CF₂Cl H OS (O)₂(Ph-4-Me)
CF₂Cl H S (O)₂Me
CF₂Cl H S (O)₂CF_Three
CF₂Cl H NO₂
CF₂Cl H NH₂
CF₂Cl H NHC (O) Me
CF₂Cl H NHC (O) OMe
CF₂Cl H NHC (O) OEt
CF₂Cl H Me
CF₂Cl H Et
CF₂Cl H n-Pr
CF₂Cl H CH₂Cl
CF₂Cl H CH₂Br
CF₂Cl H CH₂OH
CF₂Cl H CH₂NH₂
CF₂Cl H CH₂NHC (O) Me
CF₂Cl H CH₂NHC (O) Et
CF₂Cl H CH₂NHC (O) -n-Pr
CF₂Cl H CH₂NHC (O) -c-Pr
CF₂Cl H CH₂NHC (O) CH₂SMe
CF₂Cl H CH₂NHC (O) CH₂S (O)₂Me
CF₂Cl H CH₂NHC (O) CH₂SEt
CF₂Cl H CH₂NHC (O) CH₂S (O)₂Et
CF₂Cl H CH₂NHC (O) CH₂S-n-Pr
CF₂Cl H CH₂NHC (O) CH₂S (O)₂-NPR
CF₂Cl H CH₂NHC (O) CH₂S-c-Pr
CF₂Cl H CH₂NHC (O) CH₂S (O)₂-c-Pr
CF₂Cl H CH₂NHC (O) OMe
CF₂Cl H CH₂NHC (O) OEt
CF₂Cl H CH₂NHC (O) O-n-Pr
CF₂Cl H CH₂NHC (O) O-c-Pr
CF₂Cl H CH₂NHC (O) NHMe
CF₂Cl H CH₂NHC (O) NHEt
CF₂Cl H CH₂NHC (O) NH-n-Pr
CF₂Cl H CH₂NHC (O) NH-c-Pr
CF₂Cl H CH₂NO₂
CF₂Cl H CH₂-(G-1)
CF₂Cl H CH₂-(G-2)
CF₂Cl H C (O) OH
CF₂Cl H C (O) OMe
CF₂Cl H C (O) OEt
CF₂Cl H C (O) O-n-Pr
CF₂Cl H C (O) NH₂
CF₂Cl H C (O) NHMe
CF₂Cl H C (O) NHEt
CF₂Cl H C (O) NH-n-Pr
CF₂Cl H C (O) NH-c-Pr
CF₂Cl H C (O) NHCH₂-c-Pr
CF₂Cl H C (O) NHCH₂CF_Three
CF₂Cl H C (O) NH (Me) CH₂CF_Three
CF₂Cl H C (O) NH (CH₂OMe) CH₂CF_Three
CF₂Cl H C (O) NH [C (O) OMe] CH₂CF_Three
CF₂Cl H C (O) NHCH₂CH = CH₂
CF₂Cl H C (O) NHCH₂CH₂CH₂OMe
CF₂Cl H C (O) NHCH = NOMe
CF₂Cl H C (O) NHCH = NOEt
CF₂Cl H C (O) NHC (Me) = NOMe
CF₂Cl H C (O) NHC (Me) = NOEt
CF₂Cl H C (O) NHCH₂CH = NOH
CF₂Cl H C (O) NHCH₂CH = NOMe
CF₂Cl H C (O) NHCH₂(Me) = NOMe
CF₂Cl H C (O) NHCH₂CN
CF₂Cl H C (O) NHCH₂C (O) OH
CF₂Cl H C (O) NHCH₂C (O) OMe
CF₂Cl H C (O) NHCH₂C (O) OEt
CF₂Cl H C (O) NHCH₂C (O) OCH₂CF_Three
CF₂Cl H C (O) NHCH₂C (O) NH₂
CF₂Cl H C (O) NHCH₂C (O) NHMe
CF₂Cl H C (O) NHCH₂C (O) NMe₂
CF₂Cl H C (O) NHCH₂C (O) NHEt
CF₂Cl H C (O) NHCH₂C (O) NHCH₂CH₂Cl
CF₂Cl H C (O) NHCH₂C (O) NHCH₂CH₂Br
CF₂Cl H C (O) NHCH₂C (O) NHCH₂CH₂F
CF₂Cl H C (O) NHCH₂C (O) NHCH₂CF_Three
CF₂Cl H C (O) NHCH₂C (O) N (Me) CH₂CF_Three
CF₂Cl H C (O) N (Me) CH₂C (O) NHCH₂CF_Three
CF₂Cl H C (O) NHCH₂C (O) NHCH₂CH₂OH
CF₂Cl H C (O) NHCH (Me) C (O) OH
CF₂Cl H C (O) NHCH (Me) C (O) OMe
CF₂Cl H C (O) NHCH (Me) C (O) NHCH₂CH₂Cl
CF₂Cl H C (O) NHCH (Me) C (O) NHCH₂CF_Three
CF₂Cl H C (O) NHCH₂Ph
CF₂Cl H C (O) NHCH₂(Ph-4-F)
CF₂Cl H C (O) NHCH (Me) (Ph-4-F)
CF₂Cl H C (O) NHCH (Et) (Ph-4-F)
CF₂Cl H C (O) NHCH (CH₂CN) (Ph-4-F)
CF₂Cl H C (O) NHCH (CH₂OMe) (Ph-4-F)
CF₂Cl H C (O) NHCH [C (O) Me] (Ph-4-F)
CF₂Cl H C (O) NHCH [C (O) OMe] (Ph-4-F)
CF₂Cl H C (O) NHCH (Ph-4-CN)
CF₂Cl H C (O) NHCH₂CH₂Cl
CF₂Cl H C (O) NHCH₂-(2-pyridyl)
CF₂Cl H C (O) NHCH₂-(4-thiazolyl)
CF₂Cl H C (O) NHCH₂-(1,3-dioxolane-2-yl)
CF₂Cl H C (O) NHCH₂CH₂SMe
CF₂Cl H C (O) NHCH (Me) CH₂SMe
CF₂Cl H C (O) NHCH₂CH₂CH₂SMe
CF₂Cl H C (O) NHCH₂CH₂S (O) Me
CF₂Cl H C (O) NHCH (Me) CH₂S (O) Me
CF₂Cl H C (O) NHCH₂CH₂CH₂S (O) Me
CF₂Cl H C (O) NHCH₂CH₂S (O)₂Me
CF₂Cl H C (O) NHCH (Me) CH₂S (O)₂Me
CF₂Cl H C (O) NHCH₂CH₂CH₂S (O)₂Me
CF₂Cl H C (O) NHNH₂
CF₂Cl H C (O) NHNHMe
CF₂Cl H C (O) NHNMe₂
CF₂Cl H C (O) NHNHPh
CF₂Cl H C (O) NHC (O) OMe
CF₂Cl H C (O) NHC (O) OEt
CF₂Cl H C (O) NHC (O) NHMe
CF₂Cl H C (O) NHC (O) NHEt
CF₂Cl H C (O) NHC (O) NH₂
CF₂Cl H C (O) NHC (O) NMe₂
CF₂Cl H C (O) NHPh
CF₂Cl H C (O) NH (Ph-4-Cl)
CF₂Cl H C (O) NH (2-pyridyl)
CF₂Cl H C (O) NHCH₂C (O) NH-i-Pr
CF₂Cl H C (O) NHCH₂C (O) NHCH₂-i-Pr
CF₂Cl H C (O) NHCH (Me) C (O) NHCH₂-i-Pr
CF₂Cl H C (O) NHCH (Me) C (O) NHCH₂CH₂F
CF₂Cl H D-11a
CF₂Cl H D-11b
CF₂Cl H D-21a
CF₂Cl H D-35a
CF₂Cl H D-36a
CF₂Cl H D-37a
CF₂Cl H D-38a
CF₂Cl H D-39a
CF₂Cl H D-40a
CF₂Cl H D-41a
CF₂Cl F F
CF₂Cl F Cl
CF₂Cl F Br
CF₂Cl F I
CF₂Cl F CN
CF₂Cl F OH
CF₂Cl F OMe
CF₂Cl F OCH₂Ph
CF₂Cl F OS (O)₂Me
CF₂Cl F OS (O)₂CF_Three
CF₂Cl F OS (O)₂(Ph-4-Me)
CF₂Cl F S (O)₂Me
CF₂Cl F S (O)₂CF_Three
CF₂Cl F NO₂
CF₂Cl F NH₂
CF₂Cl F NHC (O) Me
CF₂Cl F NHC (O) OMe
CF₂Cl F NHC (O) OEt
CF₂Cl F Me
CF₂Cl F Et
CF₂Cl F n-Pr
CF₂Cl F CH₂Cl
CF₂Cl F CH₂Br
CF₂Cl F CH₂OH
CF₂Cl F CH₂NH₂
CF₂Cl F CH₂NHC (O) Me
CF₂Cl F CH₂NHC (O) Et
CF₂Cl F CH₂NHC (O) -n-Pr
CF₂Cl F CH₂NHC (O) -c-Pr
CF₂Cl F CH₂NHC (O) CH₂SMe
CF₂Cl F CH₂NHC (O) CH₂S (O)₂Me
CF₂Cl F CH₂NHC (O) CH₂SEt
CF₂Cl F CH₂NHC (O) CH₂S (O)₂Et
CF₂Cl F CH₂NHC (O) CH₂S-n-Pr
CF₂Cl F CH₂NHC (O) CH₂S (O)₂-NPR
CF₂Cl F CH₂NHC (O) CH₂S-c-Pr
CF₂Cl F CH₂NHC (O) CH₂S (O)₂-c-Pr
CF₂Cl F CH₂NHC (O) OMe
CF₂Cl F CH₂NHC (O) OEt
CF₂Cl F CH₂NHC (O) O-n-Pr
CF₂Cl F CH₂NHC (O) O-c-Pr
CF₂Cl F CH₂NHC (O) NHMe
CF₂Cl F CH₂NHC (O) NHEt
CF₂Cl F CH₂NHC (O) NH-n-Pr
CF₂Cl F CH₂NHC (O) NH-c-Pr
CF₂Cl F CH₂NO₂
CF₂Cl F CH₂-(G-1)
CF₂Cl F CH₂-(G-2)
CF₂Cl F C (O) OH
CF₂Cl F C (O) OMe
CF₂Cl F C (O) OEt
CF₂Cl F C (O) O-n-Pr
CF₂Cl F C (O) NH₂
CF₂Cl F C (O) NHMe
CF₂Cl F C (O) NHEt
CF₂Cl F C (O) NH-n-Pr
CF₂Cl F C (O) NH-c-Pr
CF₂Cl F C (O) NHCH₂-c-Pr
CF₂Cl F C (O) NHCH₂CF_Three
CF₂Cl F C (O) NH (Me) CH₂CF_Three
CF₂Cl F C (O) NH (CH₂OMe) CH₂CF_Three
CF₂Cl F C (O) NH [C (O) OMe] CH₂CF_Three
CF₂Cl F C (O) NHCH₂CH = CH₂
CF₂Cl F C (O) NHCH₂CH₂CH₂OMe
CF₂Cl F C (O) NHCH = NOMe
CF₂Cl F C (O) NHCH = NOEt
CF₂Cl F C (O) NHC (Me) = NOMe
CF₂Cl F C (O) NHC (Me) = NOEt
CF₂Cl F C (O) NHCH₂CH = NOH
CF₂Cl F C (O) NHCH₂CH = NOMe
CF₂Cl F C (O) NHCH₂(Me) = NOMe
CF₂Cl F C (O) NHCH₂CN
CF₂Cl F C (O) NHCH₂C (O) OH
CF₂Cl F C (O) NHCH₂C (O) OMe
CF₂Cl F C (O) NHCH₂C (O) OEt
CF₂Cl F C (O) NHCH₂C (O) OCH₂CF_Three
CF₂Cl F C (O) NHCH₂C (O) NH₂
CF₂Cl F C (O) NHCH₂C (O) NHMe
CF₂Cl F C (O) NHCH₂C (O) NMe₂
CF₂Cl F C (O) NHCH₂C (O) NHEt
CF₂Cl F C (O) NHCH₂C (O) NHCH₂CH₂Cl
CF₂Cl F C (O) NHCH₂C (O) NHCH₂CH₂Br
CF₂Cl F C (O) NHCH₂C (O) NHCH₂CH₂F
CF₂Cl F C (O) NHCH₂C (O) NHCH₂CF_Three
CF₂Cl F C (O) NHCH₂C (O) N (Me) CH₂CF_Three
CF₂Cl F C (O) N (Me) CH₂C (O) NHCH₂CF_Three
CF₂Cl F C (O) NHCH₂C (O) NHCH₂CH₂OH
CF₂Cl F C (O) NHCH (Me) C (O) OH
CF₂Cl F C (O) NHCH (Me) C (O) OMe
CF₂Cl F C (O) NHCH (Me) C (O) NHCH₂CH₂Cl
CF₂Cl F C (O) NHCH (Me) C (O) NHCH₂CF_Three
CF₂Cl F C (O) NHCH₂Ph
CF₂Cl F C (O) NHCH₂(Ph-4-F)
CF₂Cl F C (O) NHCH (Me) (Ph-4-F)
CF₂Cl F C (O) NHCH (Et) (Ph-4-F)
CF₂Cl F C (O) NHCH (CH₂CN) (Ph-4-F)
CF₂Cl F C (O) NHCH (CH₂OMe) (Ph-4-F)
CF₂Cl F C (O) NHCH [C (O) Me] (Ph-4-F)
CF₂Cl F C (O) NHCH [C (O) OMe] (Ph-4-F)
CF₂Cl F C (O) NHCH (Ph-4-CN)
CF₂Cl F C (O) NHCH₂CH₂Cl
CF₂Cl F C (O) NHCH₂-(2-pyridyl)
CF₂Cl F C (O) NHCH₂-(4-thiazolyl)
CF₂Cl F C (O) NHCH₂-(1,3-dioxolane-2-yl)
CF₂Cl F C (O) NHCH₂CH₂SMe
CF₂Cl F C (O) NHCH (Me) CH₂SMe
CF₂Cl F C (O) NHCH₂CH₂CH₂SMe
CF₂Cl F C (O) NHCH₂CH₂S (O) Me
CF₂Cl F C (O) NHCH (Me) CH₂S (O) Me
CF₂Cl F C (O) NHCH₂CH₂CH₂S (O) Me
CF₂Cl F C (O) NHCH₂CH₂S (O)₂Me
CF₂Cl F C (O) NHCH (Me) CH₂S (O)₂Me
CF₂Cl F C (O) NHCH₂CH₂CH₂S (O)₂Me
CF₂Cl F C (O) NHNH₂
CF₂Cl F C (O) NHNHMe
CF₂Cl F C (O) NHNMe₂
CF₂Cl F C (O) NHNHPh
CF₂Cl F C (O) NHC (O) OMe
CF₂Cl F C (O) NHC (O) OEt
CF₂Cl F C (O) NHC (O) NHMe
CF₂Cl F C (O) NHC (O) NHEt
CF₂Cl F C (O) NHC (O) NH₂
CF₂Cl F C (O) NHC (O) NMe₂
CF₂Cl F C (O) NHPh
CF₂Cl F C (O) NH (Ph-4-Cl)
CF₂Cl F C (O) NH (2-pyridyl)
CF₂Cl F C (O) NHCH₂C (O) NH-i-Pr
CF₂Cl F C (O) NHCH₂C (O) NHCH₂-i-Pr
CF₂Cl F C (O) NHCH (Me) C (O) NHCH₂-i-Pr
CF₂Cl F C (O) NHCH (Me) C (O) NHCH₂CH₂F
CF₂Cl F D-11a
CF₂Cl F D-11b
CF₂Cl F D-21a
CF₂Cl F D-35a
CF₂Cl F D-36a
CF₂Cl F D-37a
CF₂Cl F D-38a
CF₂Cl F D-39a
CF₂Cl F D-40a
CF₂Cl F D-41a
CF₂Cl Cl F
CF₂Cl Cl Cl
CF₂Cl Cl Br
CF₂Cl Cl I
CF₂Cl Cl CN
CF₂Cl Cl OH
CF₂Cl Cl OMe
CF₂Cl Cl OCH₂Ph
CF₂Cl Cl OS (O)₂Me
CF₂Cl Cl OS (O)₂CF_Three
CF₂Cl Cl OS (O)₂(Ph-4-Me)
CF₂Cl Cl S (O)₂Me
CF₂Cl Cl S (O)₂CF_Three
CF₂Cl Cl NO₂
CF₂Cl Cl NH₂
CF₂Cl Cl NHC (O) Me
CF₂Cl Cl NHC (O) OMe
CF₂Cl Cl NHC (O) OEt
CF₂Cl Cl Me
CF₂Cl Cl Et
CF₂Cl Cl n-Pr
CF₂Cl Cl CH₂Cl
CF₂Cl Cl CH₂Br
CF₂Cl Cl CH₂OH
CF₂Cl Cl CH₂NH₂
CF₂Cl Cl CH₂NHC (O) Me
CF₂Cl Cl CH₂NHC (O) Et
CF₂Cl Cl CH₂NHC (O) -n-Pr
CF₂Cl Cl CH₂NHC (O) -c-Pr
CF₂Cl Cl CH₂NHC (O) CH₂SMe
CF₂Cl Cl CH₂NHC (O) CH₂S (O)₂Me
CF₂Cl Cl CH₂NHC (O) CH₂SEt
CF₂Cl Cl CH₂NHC (O) CH₂S (O)₂Et
CF₂Cl Cl CH₂NHC (O) CH₂S-n-Pr
CF₂Cl Cl CH₂NHC (O) CH₂S (O)₂-NPR
CF₂Cl Cl CH₂NHC (O) CH₂S-c-Pr
CF₂Cl Cl CH₂NHC (O) CH₂S (O)₂-c-Pr
CF₂Cl Cl CH₂NHC (O) OMe
CF₂Cl Cl CH₂NHC (O) OEt
CF₂Cl Cl CH₂NHC (O) O-n-Pr
CF₂Cl Cl CH₂NHC (O) O-c-Pr
CF₂Cl Cl CH₂NHC (O) NHMe
CF₂Cl Cl CH₂NHC (O) NHEt
CF₂Cl Cl CH₂NHC (O) NH-n-Pr
CF₂Cl Cl CH₂NHC (O) NH-c-Pr
CF₂Cl Cl CH₂NO₂
CF₂Cl Cl CH₂-(G-1)
CF₂Cl Cl CH₂-(G-2)
CF₂Cl Cl C (O) OH
CF₂Cl Cl C (O) OMe
CF₂Cl Cl C (O) OEt
CF₂Cl Cl C (O) O-n-Pr
CF₂Cl Cl C (O) NH₂
CF₂Cl Cl C (O) NHMe
CF₂Cl Cl C (O) NHEt
CF₂Cl Cl C (O) NH-n-Pr
CF₂Cl Cl C (O) NH-c-Pr
CF₂Cl Cl C (O) NHCH₂-c-Pr
CF₂Cl Cl C (O) NHCH₂CF_Three
CF₂Cl Cl C (O) NH (Me) CH₂CF_Three
CF₂Cl Cl C (O) NH (CH₂OMe) CH₂CF_Three
CF₂Cl Cl C (O) NH [C (O) OMe] CH₂CF_Three
CF₂Cl Cl C (O) NHCH₂CH = CH₂
CF₂Cl Cl C (O) NHCH₂CH₂CH₂OMe
CF₂Cl Cl C (O) NHCH = NOMe
CF₂Cl Cl C (O) NHCH = NOEt
CF₂Cl Cl C (O) NHC (Me) = NOMe
CF₂Cl Cl C (O) NHC (Me) = NOEt
CF₂Cl Cl C (O) NHCH₂CH = NOH
CF₂Cl Cl C (O) NHCH₂CH = NOMe
CF₂Cl Cl C (O) NHCH₂(Me) = NOMe
CF₂Cl Cl C (O) NHCH₂CN
CF₂Cl Cl C (O) NHCH₂C (O) OH
CF₂Cl Cl C (O) NHCH₂C (O) OMe
CF₂Cl Cl C (O) NHCH₂C (O) OEt
CF₂Cl Cl C (O) NHCH₂C (O) OCH₂CF_Three
CF₂Cl Cl C (O) NHCH₂C (O) NH₂
CF₂Cl Cl C (O) NHCH₂C (O) NHMe
CF₂Cl Cl C (O) NHCH₂C (O) NMe₂
CF₂Cl Cl C (O) NHCH₂C (O) NHEt
CF₂Cl Cl C (O) NHCH₂C (O) NHCH₂CH₂Cl
CF₂Cl Cl C (O) NHCH₂C (O) NHCH₂CH₂Br
CF₂Cl Cl C (O) NHCH₂C (O) NHCH₂CH₂F
CF₂Cl Cl C (O) NHCH₂C (O) NHCH₂CF_Three
CF₂Cl Cl C (O) NHCH₂C (O) N (Me) CH₂CF_Three
CF₂Cl Cl C (O) N (Me) CH₂C (O) NHCH₂CF_Three
CF₂Cl Cl C (O) NHCH₂C (O) NHCH₂CH₂OH
CF₂Cl Cl C (O) NHCH (Me) C (O) OH
CF₂Cl Cl C (O) NHCH (Me) C (O) OMe
CF₂Cl Cl C (O) NHCH (Me) C (O) NHCH₂CH₂Cl
CF₂Cl Cl C (O) NHCH (Me) C (O) NHCH₂CF_Three
CF₂Cl Cl C (O) NHCH₂Ph
CF₂Cl Cl C (O) NHCH₂(Ph-4-F)
CF₂Cl Cl C (O) NHCH (Me) (Ph-4-F)
CF₂Cl Cl C (O) NHCH (Et) (Ph-4-F)
CF₂Cl Cl C (O) NHCH (CH₂CN) (Ph-4-F)
CF₂Cl Cl C (O) NHCH (CH₂OMe) (Ph-4-F)
CF₂Cl Cl C (O) NHCH [C (O) Me] (Ph-4-F)
CF₂Cl Cl C (O) NHCH [C (O) OMe] (Ph-4-F)
CF₂Cl Cl C (O) NHCH (Ph-4-CN)
CF₂Cl Cl C (O) NHCH₂CH₂Cl
CF₂Cl Cl C (O) NHCH₂-(2-pyridyl)
CF₂Cl Cl C (O) NHCH₂-(4-thiazolyl)
CF₂Cl Cl C (O) NHCH₂-(1,3-dioxolane-2-yl)
CF₂Cl Cl C (O) NHCH₂CH₂SMe
CF₂Cl Cl C (O) NHCH (Me) CH₂SMe
CF₂Cl Cl C (O) NHCH₂CH₂CH₂SMe
CF₂Cl Cl C (O) NHCH₂CH₂S (O) Me
CF₂Cl Cl C (O) NHCH (Me) CH₂S (O) Me
CF₂Cl Cl C (O) NHCH₂CH₂CH₂S (O) Me
CF₂Cl Cl C (O) NHCH₂CH₂S (O)₂Me
CF₂Cl Cl C (O) NHCH (Me) CH₂S (O)₂Me
CF₂Cl Cl C (O) NHCH₂CH₂CH₂S (O)₂Me
CF₂Cl Cl C (O) NHNH₂
CF₂Cl Cl C (O) NHNHMe
CF₂Cl Cl C (O) NHNMe₂
CF₂Cl Cl C (O) NHNHPh
CF₂Cl Cl C (O) NHC (O) OMe
CF₂Cl Cl C (O) NHC (O) OEt
CF₂Cl Cl C (O) NHC (O) NHMe
CF₂Cl Cl C (O) NHC (O) NHEt
CF₂Cl Cl C (O) NHC (O) NH₂
CF₂Cl Cl C (O) NHC (O) NMe₂
CF₂Cl Cl C (O) NHPh
CF₂Cl Cl C (O) NH (Ph-4-Cl)
CF₂Cl Cl C (O) NH (2-pyridyl)
CF₂Cl Cl C (O) NHCH₂C (O) NH-i-Pr
CF₂Cl Cl C (O) NHCH₂C (O) NHCH₂-i-Pr
CF₂Cl Cl C (O) NHCH (Me) C (O) NHCH₂-i-Pr
CF₂Cl Cl C (O) NHCH (Me) C (O) NHCH₂CH₂F
CF₂Cl Cl D-11a
CF₂Cl Cl D-11b
CF₂Cl Cl D-21a
CF₂Cl Cl D-35a
CF₂Cl Cl D-36a
CF₂Cl Cl D-37a
CF₂Cl Cl D-38a
CF₂Cl Cl D-39a
CF₂Cl Cl D-40a
CF₂Cl Cl D-41a
CF₂Cl Me F
CF₂Cl Me Cl
CF₂Cl Me Br
CF₂Cl Me I
CF₂Cl Me CN
CF₂Cl Me OH
CF₂Cl Me OMe
CF₂Cl Me OCH₂Ph
CF₂Cl Me OS (O)₂Me
CF₂Cl Me OS (O)₂CF_Three
CF₂Cl Me OS (O)₂(Ph-4-Me)
CF₂Cl Me S (O)₂Me
CF₂Cl Me S (O)₂CF_Three
CF₂Cl Me NO₂
CF₂Cl Me NH₂
CF₂Cl Me NHC (O) Me
CF₂Cl Me NHC (O) OMe
CF₂Cl Me NHC (O) OEt
CF₂Cl Me Me
CF₂Cl Me Et
CF₂Cl Me n-Pr
CF₂Cl Me CH₂Cl
CF₂Cl Me CH₂Br
CF₂Cl Me CH₂OH
CF₂Cl Me CH₂NH₂
CF₂Cl Me CH₂NHC (O) Me
CF₂Cl Me CH₂NHC (O) Et
CF₂Cl Me CH₂NHC (O) -n-Pr
CF₂Cl Me CH₂NHC (O) -c-Pr
CF₂Cl Me CH₂NHC (O) CH₂SMe
CF₂Cl Me CH₂NHC (O) CH₂S (O)₂Me
CF₂Cl Me CH₂NHC (O) CH₂SEt
CF₂Cl Me CH₂NHC (O) CH₂S (O)₂Et
CF₂Cl Me CH₂NHC (O) CH₂S-n-Pr
CF₂Cl Me CH₂NHC (O) CH₂S (O)₂-NPR
CF₂Cl Me CH₂NHC (O) CH₂S-c-Pr
CF₂Cl Me CH₂NHC (O) CH₂S (O)₂-c-Pr
CF₂Cl Me CH₂NHC (O) OMe
CF₂Cl Me CH₂NHC (O) OEt
CF₂Cl Me CH₂NHC (O) O-n-Pr
CF₂Cl Me CH₂NHC (O) O-c-Pr
CF₂Cl Me CH₂NHC (O) NHMe
CF₂Cl Me CH₂NHC (O) NHEt
CF₂Cl Me CH₂NHC (O) NH-n-Pr
CF₂Cl Me CH₂NHC (O) NH-c-Pr
CF₂Cl Me CH₂NO₂
CF₂Cl Me CH₂-(G-1)
CF₂Cl Me CH₂-(G-2)
CF₂Cl Me C (O) OH
CF₂Cl Me C (O) OMe
CF₂Cl Me C (O) OEt
CF₂Cl Me C (O) O-n-Pr
CF₂Cl Me C (O) NH₂
CF₂Cl Me C (O) NHMe
CF₂Cl Me C (O) NHEt
CF₂Cl Me C (O) NH-n-Pr
CF₂Cl Me C (O) NH-c-Pr
CF₂Cl Me C (O) NHCH₂-c-Pr
CF₂Cl Me C (O) NHCH₂CF_Three
CF₂Cl Me C (O) NH (Me) CH₂CF_Three
CF₂Cl Me C (O) NH (CH₂OMe) CH₂CF_Three
CF₂Cl Me C (O) NH [C (O) OMe] CH₂CF_Three
CF₂Cl Me C (O) NHCH₂CH = CH₂
CF₂Cl Me C (O) NHCH₂CH₂CH₂OMe
CF₂Cl Me C (O) NHCH = NOMe
CF₂Cl Me C (O) NHCH = NOEt
CF₂Cl Me C (O) NHC (Me) = NOMe
CF₂Cl Me C (O) NHC (Me) = NOEt
CF₂Cl Me C (O) NHCH₂CH = NOH
CF₂Cl Me C (O) NHCH₂CH = NOMe
CF₂Cl Me C (O) NHCH₂(Me) = NOMe
CF₂Cl Me C (O) NHCH₂CN
CF₂Cl Me C (O) NHCH₂C (O) OH
CF₂Cl Me C (O) NHCH₂C (O) OMe
CF₂Cl Me C (O) NHCH₂C (O) OEt
CF₂Cl Me C (O) NHCH₂C (O) OCH₂CF_Three
CF₂Cl Me C (O) NHCH₂C (O) NH₂
CF₂Cl Me C (O) NHCH₂C (O) NHMe
CF₂Cl Me C (O) NHCH₂C (O) NMe₂
CF₂Cl Me C (O) NHCH₂C (O) NHEt
CF₂Cl Me C (O) NHCH₂C (O) NHCH₂CH₂Cl
CF₂Cl Me C (O) NHCH₂C (O) NHCH₂CH₂Br
CF₂Cl Me C (O) NHCH₂C (O) NHCH₂CH₂F
CF₂Cl Me C (O) NHCH₂C (O) NHCH₂CF_Three
CF₂Cl Me C (O) NHCH₂C (O) N (Me) CH₂CF_Three
CF₂Cl Me C (O) N (Me) CH₂C (O) NHCH₂CF_Three
CF₂Cl Me C (O) NHCH₂C (O) NHCH₂CH₂OH
CF₂Cl Me C (O) NHCH (Me) C (O) OH
CF₂Cl Me C (O) NHCH (Me) C (O) OMe
CF₂Cl Me C (O) NHCH (Me) C (O) NHCH₂CH₂Cl
CF₂Cl Me C (O) NHCH (Me) C (O) NHCH₂CF_Three
CF₂Cl Me C (O) NHCH₂Ph
CF₂Cl Me C (O) NHCH₂(Ph-4-F)
CF₂Cl Me C (O) NHCH (Me) (Ph-4-F)
CF₂Cl Me C (O) NHCH (Et) (Ph-4-F)
CF₂Cl Me C (O) NHCH (CH₂CN) (Ph-4-F)
CF₂Cl Me C (O) NHCH (CH₂OMe) (Ph-4-F)
CF₂Cl Me C (O) NHCH [C (O) Me] (Ph-4-F)
CF₂Cl Me C (O) NHCH [C (O) OMe] (Ph-4-F)
CF₂Cl Me C (O) NHCH (Ph-4-CN)
CF₂Cl Me C (O) NHCH₂CH₂Cl
CF₂Cl Me C (O) NHCH₂-(2-pyridyl)
CF₂Cl Me C (O) NHCH₂-(4-thiazolyl)
CF₂Cl Me C (O) NHCH₂-(1,3-dioxolane-2-yl)
CF₂Cl Me C (O) NHCH₂CH₂SMe
CF₂Cl Me C (O) NHCH (Me) CH₂SMe
CF₂Cl Me C (O) NHCH₂CH₂CH₂SMe
CF₂Cl Me C (O) NHCH₂CH₂S (O) Me
CF₂Cl Me C (O) NHCH (Me) CH₂S (O) Me
CF₂Cl Me C (O) NHCH₂CH₂CH₂S (O) Me
CF₂Cl Me C (O) NHCH₂CH₂S (O)₂Me
CF₂Cl Me C (O) NHCH (Me) CH₂S (O)₂Me
CF₂Cl Me C (O) NHCH₂CH₂CH₂S (O)₂Me
CF₂Cl Me C (O) NHNH₂
CF₂Cl Me C (O) NHNHMe
CF₂Cl Me C (O) NHNMe₂
CF₂Cl Me C (O) NHNHPh
CF₂Cl Me C (O) NHC (O) OMe
CF₂Cl Me C (O) NHC (O) OEt
CF₂Cl Me C (O) NHC (O) NHMe
CF₂Cl Me C (O) NHC (O) NHEt
CF₂Cl Me C (O) NHC (O) NH₂
CF₂Cl Me C (O) NHC (O) NMe₂
CF₂Cl Me C (O) NHPh
CF₂Cl Me C (O) NH (Ph-4-Cl)
CF₂Cl Me C (O) NH (2-pyridyl)
CF₂Cl Me C (O) NHCH₂C (O) NH-i-Pr
CF₂Cl Me C (O) NHCH₂C (O) NHCH₂-i-Pr
CF₂Cl Me C (O) NHCH (Me) C (O) NHCH₂-i-Pr
CF₂Cl Me C (O) NHCH (Me) C (O) NHCH₂CH₂F
CF₂Cl Me D-11a
CF₂Cl Me D-11b
CF₂Cl Me D-21a
CF₂Cl Me D-35a
CF₂Cl Me D-36a
CF₂Cl Me D-37a
CF₂Cl Me D-38a
CF₂Cl Me D-39a
CF₂Cl Me D-40a
CF₂Cl Me D-41a
CF₂Cl CF_Three         F
CF₂Cl CF_Three         Cl
CF₂Cl CF_Three         Br
CF₂Cl CF_Three         I
CF₂Cl CF_Three         CN
CF₂Cl CF_Three         OH
CF₂Cl CF_Three         OMe
CF₂Cl CF_Three         OCH₂Ph
CF₂Cl CF_Three         OS (O)₂Me
CF₂Cl CF_Three         OS (O)₂CF_Three
CF₂Cl CF_Three         OS (O)₂(Ph-4-Me)
CF₂Cl CF_Three         S (O)₂Me
CF₂Cl CF_Three         S (O)₂CF_Three
CF₂Cl CF_Three         NO₂
CF₂Cl CF_Three         NH₂
CF₂Cl CF_Three         NHC (O) Me
CF₂Cl CF_Three         NHC (O) OMe
CF₂Cl CF_Three         NHC (O) OEt
CF₂Cl CF_Three         Me
CF₂Cl CF_Three         Et
CF₂Cl CF_Three         NPR
CF₂Cl CF_Three         CH₂Cl
CF₂Cl CF_Three         CH₂Br
CF₂Cl CF_Three         CH₂OH
CF₂Cl CF_Three         CH₂NH₂
CF₂Cl CF_Three         CH₂NHC (O) Me
CF₂Cl CF_Three         CH₂NHC (O) Et
CF₂Cl CF_Three         CH₂NHC (O) -n-Pr
CF₂Cl CF_Three         CH₂NHC (O) -c-Pr
CF₂Cl CF_Three         CH₂NHC (O) CH₂SMe
CF₂Cl CF_Three         CH₂NHC (O) CH₂S (O)₂Me
CF₂Cl CF_Three         CH₂NHC (O) CH₂SEt
CF₂Cl CF_Three         CH₂NHC (O) CH₂S (O)₂Et
CF₂Cl CF_Three         CH₂NHC (O) CH₂S-n-Pr
CF₂Cl CF_Three         CH₂NHC (O) CH₂S (O)₂-NPR
CF₂Cl CF_Three         CH₂NHC (O) CH₂S-c-Pr
CF₂Cl CF_Three         CH₂NHC (O) CH₂S (O)₂-c-Pr
CF₂Cl CF_Three         CH₂NHC (O) OMe
CF₂Cl CF_Three         CH₂NHC (O) OEt
CF₂Cl CF_Three         CH₂NHC (O) O-n-Pr
CF₂Cl CF_Three         CH₂NHC (O) O-c-Pr
CF₂Cl CF_Three         CH₂NHC (O) NHMe
CF₂Cl CF_Three         CH₂NHC (O) NHEt
CF₂Cl CF_Three         CH₂NHC (O) NH-n-Pr
CF₂Cl CF_Three         CH₂NHC (O) NH-c-Pr
CF₂Cl CF_Three         CH₂NO₂
CF₂Cl CF_Three         CH₂-(G-1)
CF₂Cl CF_Three         CH₂-(G-2)
CF₂Cl CF_Three         C (O) OH
CF₂Cl CF_Three         C (O) OMe
CF₂Cl CF_Three         C (O) OEt
CF₂Cl CF_Three         C (O) O-n-Pr
CF₂Cl CF_Three         C (O) NH₂
CF₂Cl CF_Three         C (O) NHMe
CF₂Cl CF_Three         C (O) NHEt
CF₂Cl CF_Three         C (O) NH-n-Pr
CF₂Cl CF_Three         C (O) NH-c-Pr
CF₂Cl CF_Three         C (O) NHCH₂-c-Pr
CF₂Cl CF_Three         C (O) NHCH₂CF_Three
CF₂Cl CF_Three         C (O) NH (Me) CH₂CF_Three
CF₂Cl CF_Three         C (O) NH (CH₂OMe) CH₂CF_Three
CF₂Cl CF_Three         C (O) NH [C (O) OMe] CH₂CF_Three
CF₂Cl CF_Three         C (O) NHCH₂CH = CH₂
CF₂Cl CF_Three         C (O) NHCH₂CH₂CH₂OMe
CF₂Cl CF_Three         C (O) NHCH = NOMe
CF₂Cl CF_Three         C (O) NHCH = NOEt
CF₂Cl CF_Three         C (O) NHC (Me) = NOMe
CF₂Cl CF_Three         C (O) NHC (Me) = NOEt
CF₂Cl CF_Three         C (O) NHCH₂CH = NOH
CF₂Cl CF_Three         C (O) NHCH₂CH = NOMe
CF₂Cl CF_Three         C (O) NHCH₂(Me) = NOMe
CF₂Cl CF_Three         C (O) NHCH₂CN
CF₂Cl CF_Three         C (O) NHCH₂C (O) OH
CF₂Cl CF_Three         C (O) NHCH₂C (O) OMe
CF₂Cl CF_Three         C (O) NHCH₂C (O) OEt
CF₂Cl CF_Three         C (O) NHCH₂C (O) OCH₂CF_Three
CF₂Cl CF_Three         C (O) NHCH₂C (O) NH₂
CF₂Cl CF_Three         C (O) NHCH₂C (O) NHMe
CF₂Cl CF_Three         C (O) NHCH₂C (O) NMe₂
CF₂Cl CF_Three         C (O) NHCH₂C (O) NHEt
CF₂Cl CF_Three         C (O) NHCH₂C (O) NHCH₂CH₂Cl
CF₂Cl CF_Three         C (O) NHCH₂C (O) NHCH₂CH₂Br
CF₂Cl CF_Three         C (O) NHCH₂C (O) NHCH₂CH₂F
CF₂Cl CF_Three         C (O) NHCH₂C (O) NHCH₂CF_Three
CF₂Cl CF_Three         C (O) NHCH₂C (O) N (Me) CH₂CF_Three
CF₂Cl CF_Three         C (O) N (Me) CH₂C (O) NHCH₂CF_Three
CF₂Cl CF_Three         C (O) NHCH₂C (O) NHCH₂CH₂OH
CF₂Cl CF_Three         C (O) NHCH (Me) C (O) OH
CF₂Cl CF_Three         C (O) NHCH (Me) C (O) OMe
CF₂Cl CF_Three         C (O) NHCH (Me) C (O) NHCH₂CH₂Cl
CF₂Cl CF_Three         C (O) NHCH (Me) C (O) NHCH₂CF_Three
CF₂Cl CF_Three         C (O) NHCH₂Ph
CF₂Cl CF_Three         C (O) NHCH₂(Ph-4-F)
CF₂Cl CF_Three         C (O) NHCH (Me) (Ph-4-F)
CF₂Cl CF_Three         C (O) NHCH (Et) (Ph-4-F)
CF₂Cl CF_Three         C (O) NHCH (CH₂CN) (Ph-4-F)
CF₂Cl CF_Three         C (O) NHCH (CH₂OMe) (Ph-4-F)
CF₂Cl CF_Three         C (O) NHCH [C (O) Me] (Ph-4-F)
CF₂Cl CF_Three         C (O) NHCH [C (O) OMe] (Ph-4-F)
CF₂Cl CF_Three         C (O) NHCH (Ph-4-CN)
CF₂Cl CF_Three         C (O) NHCH₂CH₂Cl
CF₂Cl CF_Three         C (O) NHCH₂-(2-pyridyl)
CF₂Cl CF_Three         C (O) NHCH₂-(4-thiazolyl)
CF₂Cl CF_Three         C (O) NHCH₂-(1,3-dioxolane-2-yl)
CF₂Cl CF_Three         C (O) NHCH₂CH₂SMe
CF₂Cl CF_Three         C (O) NHCH (Me) CH₂SMe
CF₂Cl CF_Three         C (O) NHCH₂CH₂CH₂SMe
CF₂Cl CF_Three         C (O) NHCH₂CH₂S (O) Me
CF₂Cl CF_Three         C (O) NHCH (Me) CH₂S (O) Me
CF₂Cl CF_Three         C (O) NHCH₂CH₂CH₂S (O) Me
CF₂Cl CF_Three         C (O) NHCH₂CH₂S (O)₂Me
CF₂Cl CF_Three         C (O) NHCH (Me) CH₂S (O)₂Me
CF₂Cl CF_Three         C (O) NHCH₂CH₂CH₂S (O)₂Me
CF₂Cl CF_Three         C (O) NHNH₂
CF₂Cl CF_Three         C (O) NHNHMe
CF₂Cl CF_Three         C (O) NHNMe₂
CF₂Cl CF_Three         C (O) NHNHPh
CF₂Cl CF_Three         C (O) NHC (O) OMe
CF₂Cl CF_Three         C (O) NHC (O) OEt
CF₂Cl CF_Three         C (O) NHC (O) NHMe
CF₂Cl CF_Three         C (O) NHC (O) NHEt
CF₂Cl CF_Three         C (O) NHC (O) NH₂
CF₂Cl CF_Three         C (O) NHC (O) NMe₂
CF₂Cl CF_Three         C (O) NHPh
CF₂Cl CF_Three         C (O) NH (Ph-4-Cl)
CF₂Cl CF_Three         C (O) NH (2-pyridyl)
CF₂Cl CF_Three         C (O) NHCH₂C (O) NH-i-Pr
CF₂Cl CF_Three         C (O) NHCH₂C (O) NHCH₂-i-Pr
CF₂Cl CF_Three         C (O) NHCH (Me) C (O) NHCH₂-i-Pr
CF₂Cl CF_Three         C (O) NHCH (Me) C (O) NHCH₂CH₂F
CF₂Cl CF_Three         D-11a
CF₂Cl CF_Three         D-11b
CF₂Cl CF_Three         D-21a
CF₂Cl CF_Three         D-35a
CF₂Cl CF_Three         D-36a
CF₂Cl CF_Three         D-37a
CF₂Cl CF_Three         D-38a
CF₂Cl CF_Three         D-39a
CF₂Cl CF_Three         D-40a
CF₂Cl CF_Three         D-41a
CF₂Cl NO₂         F
CF₂Cl NO₂         Cl
CF₂Cl NO₂         Br
CF₂Cl NO₂         I
CF₂Cl NO₂         CN
CF₂Cl NO₂         OH
CF₂Cl NO₂         OMe
CF₂Cl NO₂         OCH₂Ph
CF₂Cl NO₂         OS (O)₂Me
CF₂Cl NO₂         OS (O)₂CF_Three
CF₂Cl NO₂         OS (O)₂(Ph-4-Me)
CF₂Cl NO₂         S (O)₂Me
CF₂Cl NO₂         S (O)₂CF_Three
CF₂Cl NO₂         NO₂
CF₂Cl NO₂         NH₂
CF₂Cl NO₂         NHC (O) Me
CF₂Cl NO₂         NHC (O) OMe
CF₂Cl NO₂         NHC (O) OEt
CF₂Cl NO₂         Me
CF₂Cl NO₂         Et
CF₂Cl NO₂         NPR
CF₂Cl NO₂         CH₂Cl
CF₂Cl NO₂         CH₂Br
CF₂Cl NO₂         CH₂OH
CF₂Cl NO₂         CH₂NH₂
CF₂Cl NO₂         CH₂NHC (O) Me
CF₂Cl NO₂         CH₂NHC (O) Et
CF₂Cl NO₂         CH₂NHC (O) -n-Pr
CF₂Cl NO₂         CH₂NHC (O) -c-Pr
CF₂Cl NO₂         CH₂NHC (O) CH₂SMe
CF₂Cl NO₂         CH₂NHC (O) CH₂S (O)₂Me
CF₂Cl NO₂         CH₂NHC (O) CH₂SEt
CF₂Cl NO₂         CH₂NHC (O) CH₂S (O)₂Et
CF₂Cl NO₂         CH₂NHC (O) CH₂S-n-Pr
CF₂Cl NO₂         CH₂NHC (O) CH₂S (O)₂-NPR
CF₂Cl NO₂         CH₂NHC (O) CH₂S-c-Pr
CF₂Cl NO₂         CH₂NHC (O) CH₂S (O)₂-c-Pr
CF₂Cl NO₂         CH₂NHC (O) OMe
CF₂Cl NO₂         CH₂NHC (O) OEt
CF₂Cl NO₂         CH₂NHC (O) O-n-Pr
CF₂Cl NO₂         CH₂NHC (O) O-c-Pr
CF₂Cl NO₂         CH₂NHC (O) NHMe
CF₂Cl NO₂         CH₂NHC (O) NHEt
CF₂Cl NO₂         CH₂NHC (O) NH-n-Pr
CF₂Cl NO₂         CH₂NHC (O) NH-c-Pr
CF₂Cl NO₂         CH₂NO₂
CF₂Cl NO₂         CH₂-(G-1)
CF₂Cl NO₂         CH₂-(G-2)
CF₂Cl NO₂         C (O) OH
CF₂Cl NO₂         C (O) OMe
CF₂Cl NO₂         C (O) OEt
CF₂Cl NO₂         C (O) O-n-Pr
CF₂Cl NO₂         C (O) NH₂
CF₂Cl NO₂         C (O) NHMe
CF₂Cl NO₂         C (O) NHEt
CF₂Cl NO₂         C (O) NH-n-Pr
CF₂Cl NO₂         C (O) NH-c-Pr
CF₂Cl NO₂         C (O) NHCH₂-c-Pr
CF₂Cl NO₂         C (O) NHCH₂CF_Three
CF₂Cl NO₂         C (O) NH (Me) CH₂CF_Three
CF₂Cl NO₂         C (O) NH (CH₂OMe) CH₂CF_Three
CF₂Cl NO₂         C (O) NH [C (O) OMe] CH₂CF_Three
CF₂Cl NO₂         C (O) NHCH₂CH = CH₂
CF₂Cl NO₂         C (O) NHCH₂CH₂CH₂OMe
CF₂Cl NO₂         C (O) NHCH = NOMe
CF₂Cl NO₂         C (O) NHCH = NOEt
CF₂Cl NO₂         C (O) NHC (Me) = NOMe
CF₂Cl NO₂         C (O) NHC (Me) = NOEt
CF₂Cl NO₂         C (O) NHCH₂CH = NOH
CF₂Cl NO₂         C (O) NHCH₂CH = NOMe
CF₂Cl NO₂         C (O) NHCH₂(Me) = NOMe
CF₂Cl NO₂         C (O) NHCH₂CN
CF₂Cl NO₂         C (O) NHCH₂C (O) OH
CF₂Cl NO₂         C (O) NHCH₂C (O) OMe
CF₂Cl NO₂         C (O) NHCH₂C (O) OEt
CF₂Cl NO₂         C (O) NHCH₂C (O) OCH₂CF_Three
CF₂Cl NO₂         C (O) NHCH₂C (O) NH₂
CF₂Cl NO₂         C (O) NHCH₂C (O) NHMe
CF₂Cl NO₂         C (O) NHCH₂C (O) NMe₂
CF₂Cl NO₂         C (O) NHCH₂C (O) NHEt
CF₂Cl NO₂         C (O) NHCH₂C (O) NHCH₂CH₂Cl
CF₂Cl NO₂         C (O) NHCH₂C (O) NHCH₂CH₂Br
CF₂Cl NO₂         C (O) NHCH₂C (O) NHCH₂CH₂F
CF₂Cl NO₂         C (O) NHCH₂C (O) NHCH₂CF_Three
CF₂Cl NO₂         C (O) NHCH₂C (O) N (Me) CH₂CF_Three
CF₂Cl NO₂         C (O) N (Me) CH₂C (O) NHCH₂CF_Three
CF₂Cl NO₂         C (O) NHCH₂C (O) NHCH₂CH₂OH
CF₂Cl NO₂         C (O) NHCH (Me) C (O) OH
CF₂Cl NO₂         C (O) NHCH (Me) C (O) OMe
CF₂Cl NO₂         C (O) NHCH (Me) C (O) NHCH₂CH₂Cl
CF₂Cl NO₂         C (O) NHCH (Me) C (O) NHCH₂CF_Three
CF₂Cl NO₂         C (O) NHCH₂Ph
CF₂Cl NO₂         C (O) NHCH₂(Ph-4-F)
CF₂Cl NO₂         C (O) NHCH (Me) (Ph-4-F)
CF₂Cl NO₂         C (O) NHCH (Et) (Ph-4-F)
CF₂Cl NO₂         C (O) NHCH (CH₂CN) (Ph-4-F)
CF₂Cl NO₂         C (O) NHCH (CH₂OMe) (Ph-4-F)
CF₂Cl NO₂         C (O) NHCH [C (O) Me] (Ph-4-F)
CF₂Cl NO₂         C (O) NHCH [C (O) OMe] (Ph-4-F)
CF₂Cl NO₂         C (O) NHCH (Ph-4-CN)
CF₂Cl NO₂         C (O) NHCH₂CH₂Cl
CF₂Cl NO₂         C (O) NHCH₂-(2-pyridyl)
CF₂Cl NO₂         C (O) NHCH₂-(4-thiazolyl)
CF₂Cl NO₂         C (O) NHCH₂-(1,3-dioxolane-2-yl)
CF₂Cl NO₂         C (O) NHCH₂CH₂SMe
CF₂Cl NO₂         C (O) NHCH (Me) CH₂SMe
CF₂Cl NO₂         C (O) NHCH₂CH₂CH₂SMe
CF₂Cl NO₂         C (O) NHCH₂CH₂S (O) Me
CF₂Cl NO₂         C (O) NHCH (Me) CH₂S (O) Me
CF₂Cl NO₂         C (O) NHCH₂CH₂CH₂S (O) Me
CF₂Cl NO₂         C (O) NHCH₂CH₂S (O)₂Me
CF₂Cl NO₂         C (O) NHCH (Me) CH₂S (O)₂Me
CF₂Cl NO₂         C (O) NHCH₂CH₂CH₂S (O)₂Me
CF₂Cl NO₂         C (O) NHNH₂
CF₂Cl NO₂         C (O) NHNHMe
CF₂Cl NO₂         C (O) NHNMe₂
CF₂Cl NO₂         C (O) NHNHPh
CF₂Cl NO₂         C (O) NHC (O) OMe
CF₂Cl NO₂         C (O) NHC (O) OEt
CF₂Cl NO₂         C (O) NHC (O) NHMe
CF₂Cl NO₂         C (O) NHC (O) NHEt
CF₂Cl NO₂         C (O) NHC (O) NH₂
CF₂Cl NO₂         C (O) NHC (O) NMe₂
CF₂Cl NO₂         C (O) NHPh
CF₂Cl NO₂         C (O) NH (Ph-4-Cl)
CF₂Cl NO₂         C (O) NH (2-pyridyl)
CF₂Cl NO₂         C (O) NHCH₂C (O) NH-i-Pr
CF₂Cl NO₂         C (O) NHCH₂C (O) NHCH₂-i-Pr
CF₂Cl NO₂         C (O) NHCH (Me) C (O) NHCH₂-i-Pr
CF₂Cl NO₂         C (O) NHCH (Me) C (O) NHCH₂CH₂F
CF₂Cl NO₂         D-11a
CF₂Cl NO₂         D-11b
CF₂Cl NO₂         D-21a
CF₂Cl NO₂         D-35a
CF₂Cl NO₂         D-36a
CF₂Cl NO₂         D-37a
CF₂Cl NO₂         D-38a
CF₂Cl NO₂         D-39a
CF₂Cl NO₂         D-40a
CF₂Cl NO₂         D-41a
CF₂Cl CN F
CF₂Cl CN Cl
CF₂Cl CN Br
CF₂Cl CN I
CF₂Cl CN CN
CF₂Cl CN OH
CF₂Cl CN OMe
CF₂Cl CN OCH₂Ph
CF₂Cl CN OS (O)₂Me
CF₂Cl CN OS (O)₂CF_Three
CF₂Cl CN OS (O)₂(Ph-4-Me)
CF₂Cl CN S (O)₂Me
CF₂Cl CN S (O)₂CF_Three
CF₂Cl CN NO₂
CF₂Cl CN NH₂
CF₂Cl CN NHC (O) Me
CF₂Cl CN NHC (O) OMe
CF₂Cl CN NHC (O) OEt
CF₂Cl CN Me
CF₂Cl CN Et
CF₂Cl CN n-Pr
CF₂Cl CN CH₂Cl
CF₂Cl CN CH₂Br
CF₂Cl CN CH₂OH
CF₂Cl CN CH₂NH₂
CF₂Cl CN CH₂NHC (O) Me
CF₂Cl CN CH₂NHC (O) Et
CF₂Cl CN CH₂NHC (O) -n-Pr
CF₂Cl CN CH₂NHC (O) -c-Pr
CF₂Cl CN CH₂NHC (O) CH₂SMe
CF₂Cl CN CH₂NHC (O) CH₂S (O)₂Me
CF₂Cl CN CH₂NHC (O) CH₂SEt
CF₂Cl CN CH₂NHC (O) CH₂S (O)₂Et
CF₂Cl CN CH₂NHC (O) CH₂S-n-Pr
CF₂Cl CN CH₂NHC (O) CH₂S (O)₂-NPR
CF₂Cl CN CH₂NHC (O) CH₂S-c-Pr
CF₂Cl CN CH₂NHC (O) CH₂S (O)₂-c-Pr
CF₂Cl CN CH₂NHC (O) OMe
CF₂Cl CN CH₂NHC (O) OEt
CF₂Cl CN CH₂NHC (O) O-n-Pr
CF₂Cl CN CH₂NHC (O) O-c-Pr
CF₂Cl CN CH₂NHC (O) NHMe
CF₂Cl CN CH₂NHC (O) NHEt
CF₂Cl CN CH₂NHC (O) NH-n-Pr
CF₂Cl CN CH₂NHC (O) NH-c-Pr
CF₂Cl CN CH₂NO₂
CF₂Cl CN CH₂-(G-1)
CF₂Cl CN CH₂-(G-2)
CF₂Cl CN C (O) OH
CF₂Cl CN C (O) OMe
CF₂Cl CN C (O) OEt
CF₂Cl CN C (O) O-n-Pr
CF₂Cl CN C (O) NH₂
CF₂Cl CN C (O) NHMe
CF₂Cl CN C (O) NHEt
CF₂Cl CN C (O) NH-n-Pr
CF₂Cl CN C (O) NH-c-Pr
CF₂Cl CN C (O) NHCH₂-c-Pr
CF₂Cl CN C (O) NHCH₂CF_Three
CF₂Cl CN C (O) NH (Me) CH₂CF_Three
CF₂Cl CN C (O) NH (CH₂OMe) CH₂CF_Three
CF₂Cl CN C (O) NH [C (O) OMe] CH₂CF_Three
CF₂Cl CN C (O) NHCH₂CH = CH₂
CF₂Cl CN C (O) NHCH₂CH₂CH₂OMe
CF₂Cl CN C (O) NHCH = NOMe
CF₂Cl CN C (O) NHCH = NOEt
CF₂Cl CN C (O) NHC (Me) = NOMe
CF₂Cl CN C (O) NHC (Me) = NOEt
CF₂Cl CN C (O) NHCH₂CH = NOH
CF₂Cl CN C (O) NHCH₂CH = NOMe
CF₂Cl CN C (O) NHCH₂(Me) = NOMe
CF₂Cl CN C (O) NHCH₂CN
CF₂Cl CN C (O) NHCH₂C (O) OH
CF₂Cl CN C (O) NHCH₂C (O) OMe
CF₂Cl CN C (O) NHCH₂C (O) OEt
CF₂Cl CN C (O) NHCH₂C (O) OCH₂CF_Three
CF₂Cl CN C (O) NHCH₂C (O) NH₂
CF₂Cl CN C (O) NHCH₂C (O) NHMe
CF₂Cl CN C (O) NHCH₂C (O) NMe₂
CF₂Cl CN C (O) NHCH₂C (O) NHEt
CF₂Cl CN C (O) NHCH₂C (O) NHCH₂CH₂Cl
CF₂Cl CN C (O) NHCH₂C (O) NHCH₂CH₂Br
CF₂Cl CN C (O) NHCH₂C (O) NHCH₂CH₂F
CF₂Cl CN C (O) NHCH₂C (O) NHCH₂CF_Three
CF₂Cl CN C (O) NHCH₂C (O) N (Me) CH₂CF_Three
CF₂Cl CN C (O) N (Me) CH₂C (O) NHCH₂CF_Three
CF₂Cl CN C (O) NHCH₂C (O) NHCH₂CH₂OH
CF₂Cl CN C (O) NHCH (Me) C (O) OH
CF₂Cl CN C (O) NHCH (Me) C (O) OMe
CF₂Cl CN C (O) NHCH (Me) C (O) NHCH₂CH₂Cl
CF₂Cl CN C (O) NHCH (Me) C (O) NHCH₂CF_Three
CF₂Cl CN C (O) NHCH₂Ph
CF₂Cl CN C (O) NHCH₂(Ph-4-F)
CF₂Cl CN C (O) NHCH (Me) (Ph-4-F)
CF₂Cl CN C (O) NHCH (Et) (Ph-4-F)
CF₂Cl CN C (O) NHCH (CH₂CN) (Ph-4-F)
CF₂Cl CN C (O) NHCH (CH₂OMe) (Ph-4-F)
CF₂Cl CN C (O) NHCH [C (O) Me] (Ph-4-F)
CF₂Cl CN C (O) NHCH [C (O) OMe] (Ph-4-F)
CF₂Cl CN C (O) NHCH (Ph-4-CN)
CF₂Cl CN C (O) NHCH₂CH₂Cl
CF₂Cl CN C (O) NHCH₂-(2-pyridyl)
CF₂Cl CN C (O) NHCH₂-(4-thiazolyl)
CF₂Cl CN C (O) NHCH₂-(1,3-dioxolane-2-yl)
CF₂Cl CN C (O) NHCH₂CH₂SMe
CF₂Cl CN C (O) NHCH (Me) CH₂SMe
CF₂Cl CN C (O) NHCH₂CH₂CH₂SMe
CF₂Cl CN C (O) NHCH₂CH₂S (O) Me
CF₂Cl CN C (O) NHCH (Me) CH₂S (O) Me
CF₂Cl CN C (O) NHCH₂CH₂CH₂S (O) Me
CF₂Cl CN C (O) NHCH₂CH₂S (O)₂Me
CF₂Cl CN C (O) NHCH (Me) CH₂S (O)₂Me
CF₂Cl CN C (O) NHCH₂CH₂CH₂S (O)₂Me
CF₂Cl CN C (O) NHNH₂
CF₂Cl CN C (O) NHNHMe
CF₂Cl CN C (O) NHNMe₂
CF₂Cl CN C (O) NHNHPh
CF₂Cl CN C (O) NHC (O) OMe
CF₂Cl CN C (O) NHC (O) OEt
CF₂Cl CN C (O) NHC (O) NHMe
CF₂Cl CN C (O) NHC (O) NHEt
CF₂Cl CN C (O) NHC (O) NH₂
CF₂Cl CN C (O) NHC (O) NMe₂
CF₂Cl CN C (O) NHPh
CF₂Cl CN C (O) NH (Ph-4-Cl)
CF₂Cl CN C (O) NH (2-pyridyl)
CF₂Cl CN C (O) NHCH₂C (O) NH-i-Pr
CF₂Cl CN C (O) NHCH₂C (O) NHCH₂-i-Pr
CF₂Cl CN C (O) NHCH (Me) C (O) NHCH₂-i-Pr
CF₂Cl CN C (O) NHCH (Me) C (O) NHCH₂CH₂F
CF₂Cl CN D-11a
CF₂Cl CN D-11b
CF₂Cl CN D-21a
CF₂Cl CN D-35a
CF₂Cl CN D-36a
CF₂Cl CN D-37a
CF₂Cl CN D-38a
CF₂Cl CN D-39a
CF₂Cl CN D-40a
CF₂Cl CN D-41a
―――――――――――――――――――――――――――――――――

  Examples of the present invention are shown below, but the present invention is not limited to these examples.

[Synthesis example]
Example 1
Production of 1- (3,5-dichlorophenyl) -2,2,2-trifluoro-1-methoxyethanol 15.0 g of 1- (3,5-dichlorophenyl) -2,2,2-trifluoroethanone (61. 7 mmol) was added with 30.0 g (938 mmol) of methanol and stirred overnight at room temperature. After completion of the stirring, the reaction solution was concentrated under reduced pressure to obtain 16.7 g (60.6 mmol) of 1- (3,5-dichlorophenyl) -2,2,2-trifluoro-1-methoxyethanol which is the target product. ) Was obtained as a white solid.

As a result of measuring TG-DTA, an endothermic peak having an apex of 87.5 ° C. and an endothermic peak having an apex of 116.9 ° C. were observed.
(Measurement device: Thermo plus TG 8120 manufactured by Rigaku
Standard substance: Al ₂ O ₃
Temperature rising rate: 5.0 ° C / min Sample pan: Al)
Further, as a result of measuring DSC, an endothermic peak having an apex of 84.1 ° C. was observed.

(Measuring device: Thermo plus DSC 8230 manufactured by Rigaku
Standard substance: Al ₂ O ₃
Temperature rising rate: 10.0 ° C / min Sample pan: SUS)
¹ H-NMR (CDCl ₃ , TMS (0ppm), 400MHz) δ 7.53 (d, J = 1.8Hz, 2H), 7.45 (t, J = 1.8Hz, 1H), 3.27 (s, 3H), 3.11 (s , 1H).

(Measurement device: INOVA400 manufactured by Varian
Reference substance: Tetramethylsilane 0ppm
Measuring solvent: deuterated chloroform)
¹⁹ F-NMR (CDCl ₃ , trifluoromethylbenzene (-63.24 ppm), 400 MHz) δ-84.3.

(Measurement device: INOVA400 manufactured by Varian
Reference substance: Benzotrifluoride -63.24ppm
Measuring solvent: deuterated chloroform)
Example 2
Preparation of 1- (3-bromo-5- (trifluoromethyl) phenyl) -2,2,2-trifluoro-1-methoxyethanol 1- (3-bromo-5- (trifluoromethyl) phenyl) -2 Then, 10.0 g of methanol was added to 5.0 g (15.6 mmol) of 2,2-trifluoroethanone and stirred overnight at room temperature. After completion of the stirring, the solvent is distilled off under reduced pressure to obtain 1- (3-bromo-5- (trifluoromethyl) phenyl) -2,2,2-trifluoro-1-methoxyethanol which is the target product. 5.3 g (15.0 mmol) was obtained as a white solid.

As a result of measuring TG-DTA, an endothermic peak having a peak at 59.3 ° C. and an endothermic peak having a peak at 110.3 ° C. were observed.
(Measurement device: Thermo plus TG 8120 manufactured by Rigaku
Standard substance: Al ₂ O ₃
Temperature rising rate: 5.0 ° C / min Sample pan: Al)
As a result of measuring DSC, an endothermic peak having a peak at 54.9 ° C. and an endothermic peak having a peak at 90.6 ° C. were observed.
(Measuring device: Thermo plus DSC 8230 manufactured by Rigaku
Standard substance: Al ₂ O ₃
Temperature rising rate: 10.0 ° C / min Sample pan: SUS)
¹ H-NMR (CDCl ₃ , TMS (0 ppm), 400 MHz) δ 7.98 (s, 1H), 7.86 (s, 1H), 7.83 (s, 1H), 3.27 (s, 3H), 3.19 (s, 1H) .

(Measurement device: INOVA400 manufactured by Varian
Reference substance: Tetramethylsilane 0ppm
Measuring solvent: deuterated chloroform)
¹⁹ F-NMR (CDCl ₃ , trifluoromethylbenzene (-63.24 ppm), 400 MHz) δ -63.3, -84.3.

(Measurement device: INOVA400 manufactured by Varian
Reference substance: Benzotrifluoride -63.24ppm
Measuring solvent: deuterated chloroform)
Example 3-1
Production of 1- (3,5-dichlorophenyl) -2,2,2-trifluoroethane-1,1-diol 4.0 g of 1- (3,5-dichlorophenyl) -2,2,2-trifluoroethanone To 16.5 mmol), 0.889 g (49.4 mmol) of distilled water and 12.5 g of ethyl acetate were added and stirred at room temperature for 3 days. After completion of the stirring, about 1 ml of the reaction solution was collected in an NMR tube, and ¹⁹ F-NMR was measured. As a result, 1- (3,5-dichlorophenyl) -2,2,2-trifluoroethane-1,1 was calculated from the integration ratio. It was confirmed that the mixing ratio of diol to 1- (3,5-dichlorophenyl) -2,2,2-trifluoroethanone was> 99: 1.
¹⁹ F-NMR (AcOEt, trifluoromethylbenzene (-63.24 ppm), 400 MHz) δ-84.5.

(Measurement device: INOVA400 manufactured by Varian
Reference substance: Benzotrifluoride -63.24ppm
Measuring solvent: ethyl acetate)
Comparative Example 1
1- (3,5-dichlorophenyl) -2,2,2-trifluoroethanone was dissolved in ethyl acetate, and ¹⁹ F-NMR was measured.
¹⁹ F-NMR (AcOEt, trifluoromethylbenzene (-63.24 ppm), 400 MHz) δ-72.4.

Example 3-2
To 0.50 g (2.06 mmol) of 1- (3,5-dichlorophenyl) -2,2,2-trifluoroethanone was added 2.27 ml of distilled water, and the mixture was stirred overnight at room temperature. After stirring, about 1 ml of the supernatant of the reaction solution was collected in an NMR tube and measured for ¹⁹ F-NMR. As a result, 1- (3,5-dichlorophenyl) -2,2,2-trifluoroethane-1 was obtained from the integration ratio. , 1-diol and 1- (3,5-dichlorophenyl) -2,2,2-trifluoroethanone was confirmed to be 81:19.
¹⁹ F-NMR (H ₂ O, trifluoromethylbenzene (-63.24 ppm), 400 MHz) δ-72.4 (1- (3,5-dichlorophenyl) -2,2,2-trifluoroethanone), -83.7 (1- (3 , 5-dichlorophenyl) -2,2,2-trifluoroethane-1,1-diol).

(Measurement device: INOVA400 manufactured by Varian
Reference substance: Benzotrifluoride -63.24ppm
Measuring solvent: water)
Example 4
Preparation of 1- (3,5-dichlorophenyl) -2,2,2-trifluoroethane-1,1-diol sodium salt 1- (3,5-dichlorophenyl) -2,2,2-trifluoroethanone To 50 g (2.06 mmol), 2.27 ml (2.27 mmol) of 1N sodium hydroxide aqueous solution was added and stirred at room temperature for 2 hours. After completion of the stirring, about 1 ml of the reaction solution was collected in an NMR tube, and ¹⁹ F-NMR was measured. As a result, 1- (3,5-dichlorophenyl) -2,2,2-trifluoroethane-1,1 was calculated from the integration ratio. -The mixing ratio of the diol sodium salt and 1- (3,5-dichlorophenyl) -2,2,2-trifluoroethanone was confirmed to be> 99: 1.
¹⁹ F-NMR (H ₂ O, trifluoromethylbenzene (-63.24 ppm), 700 MHz) δ-81.0.

(Measurement device: JNM-ECA700 manufactured by JEOL
Reference substance: Benzotrifluoride -63.24ppm
Measuring solvent: water)
¹³ C-NMR (H ₂ O, 3- (trimethylsilyl) propionic-2,2,3,3-d ₄ acid sodium salt (0ppm), 700MHz) δ 150, 137, 131, 129, 127 (q, J = 294Hz), 98.8 (q, J = 30.4Hz).

(Measurement device: JNM-ECA700 manufactured by JEOL
Reference substance: sodium 3- (trimethylsilyl) propionate-2,2,3,3-d ₄ 0 ppm
Measuring solvent: water)
Comparative Example 2
1- (3,5-dichlorophenyl) -2,2,2-trifluoroethanone was dissolved in deuterated chloroform, and ¹³ C-NMR was measured.
¹³ C-NMR (CDCl ₃ , chloroform (77.00 ppm), 500 MHz) δ 179 (q, J = 36.5 Hz), 136, 135, 132, 128, 116 (q, J = 291 Hz).

(Measuring device: ECP500 manufactured by JEOL
Reference substance: chloroform 77.00ppm
Measuring solvent: deuterated chloroform)
Example 5
4- (3- (3,5-Dichlorophenyl) -4,4,4-trifluoro-3-hydroxybutanoyl) -2-methylbenzoic acid Preparation of diethylamine salt 4-acetyl-2-methylbenzoic acid 1.20 g (6.7 mmol), 1- (3,5-dichlorophenyl) -2,2,2-trifluoro-1-methoxyethanol (2.04 g, 7.4 mmol) was charged with ethyl acetate (6.0 g) and diethylamine (0.74 g). The mixture was added and stirred at 50 ° C. for 20 hours. After the completion of stirring, 3.6 g of toluene was added, and the mixture was gradually cooled to room temperature, and further stirred at room temperature for 3 days. After completion of the stirring, the solid precipitated in the reaction solution was taken out by filtration. The obtained solid was washed with 2.4 g of toluene to give 4- (3- (3,5-dichlorophenyl) -4,4,4-trifluoro-3-hydroxybutanoyl) -2- 2.77 g of methyl benzoic acid diethylamine salt was obtained as a white solid.

Melting point: 116-119 ° C
Example 6
Preparation of 4- (3- (3,5-dichlorophenyl) -4,4,4-trifluoro-3-hydroxybutanoyl) -2-methylbenzoic acid 1.20 g of 4-acetyl-2-methylbenzoic acid (6 0.7 mmol), 1- (3,5-dichlorophenyl) -2,2,2-trifluoro-1-methoxyethanol (2.04 g, 7.4 mmol), distilled water (12 g), potassium carbonate (1.12 g, 8.1 mmol) ) And 52 mg of sodium laurate were added and stirred at 70 ° C. for 7 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and further stirred at room temperature for 3 days. After completion of the reaction, 1.5 ml of concentrated hydrochloric acid was added to the reaction solution, followed by extraction with ethyl acetate (15 ml × 2). The obtained organic layer was dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained solid was washed with a mixed solution of toluene-ethyl acetate 5: 1 to give 4- (3- (3,5-dichlorophenyl) -4,4,4-trifluoro-3-hydroxybutanoyl which is the target product. ) -2-methylbenzoic acid (2.25 g) was obtained as a white solid.

Melting point: 160-163 ° C
[Reference example]
Reference example 1
13.6 ml (13.6 mmol) of 1N sodium hydroxide aqueous solution was added to a solution of 3.00 g (12.4 mmol) of 1- (3,5-dichlorophenyl) -2,2,2-trifluoroethanone in 13.2 ml of heptane on ice. It was dripped under cooling. After completion of dropping, the mixture was stirred at the same temperature for 2 hours, and then the aqueous layer was separated. To the obtained aqueous layer, 13.2 ml of heptane was added under ice cooling, and the mixture was further stirred at the same temperature for 2 hours. After stirring, the aqueous layer was separated. To the resulting aqueous layer, 13.2 ml of heptane was added, and 1.24 ml (14.8 mmol) of concentrated hydrochloric acid was added dropwise under ice cooling. After completion of dropping, the mixture was stirred at the same temperature for 2 hours. After completion of stirring, the organic layer was separated. To the remaining aqueous layer, 13.2 ml of heptane was added and stirred at 0 ° C. for 2 hours. After completion of stirring, the organic layer was separated. The obtained organic layers were combined and concentrated under reduced pressure, and heptane solution of 2.76 g (11.4 mmol, HPLC quantitative analysis value) of 1- (3,5-dichlorophenyl) -2,2,2-trifluoroethanone. 4.02 g was obtained.
¹⁹ F-NMR (CDCl ₃ , trifluoromethylbenzene (-63.24 ppm), 400 MHz) δ-72.2.

(Measurement device: INOVA400 manufactured by Varian
Reference substance: Benzotrifluoride -63.24ppm
Measuring solvent: deuterated chloroform)
HPLC quantitative analysis conditions Equipment: LC-20A manufactured by Shimadzu Corporation
Column: Inertsil Ph-3 (particle diameter 5 μm, 4.0 mm id X 250 mm) manufactured by GL Sciences
Eluent: acetonitrile / water / acetic acid = 1/1 / 0.001 (volume ratio)
Oven temperature: 40 ° C
Flow rate: 1.0 ml / min.
Detection wavelength: 220 nm

  The production method and acetal compound of the present invention are useful as a production method and production intermediate of an isoxazoline compound intermediate having excellent pest control activity.

Claims (12)

Formula (1):

[Wherein, X ¹ represents a hydrogen atom, a halogen atom, cyano, nitro, —SF ₅ , C ₁ -C ₄ haloalkyl, C ₁ -C ₄ haloalkoxy or C ₁ -C ₄ haloalkylthio,
X ² represents a hydrogen atom, a halogen atom, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ haloalkoxy or C ₁ -C ₄ haloalkylthio,
X ³ represents a hydrogen atom, a halogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₄ haloalkyl or C ₁ -C ₄ haloalkoxy,
R ¹ represents a hydrogen atom or C ₁ -C ₄ alkyl;
X represents a C ₁ -C ₄ haloalkyl or C ₃ -C ₆ halocycloalkyl. ]
Or a salt thereof. In equation (1),
X ¹ represents a halogen atom, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ haloalkoxy or C ₁ -C ₄ haloalkylthio,
X ³ represents a hydrogen atom, a halogen atom, C ₁ -C ₄ haloalkyl or C ₁ -C ₄ haloalkoxy,
The substituted acetal compound or a salt thereof according to claim ₁ , wherein R ¹ represents C ₁ -C ₄ alkyl. In equation (1),
X ² is a halogen atom, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ haloalkoxy or C ₁ -C ₄ haloalkylthio,
R ¹ represents methyl or ethyl,
The substituted acetal compound or a salt thereof according to claim 2, wherein X represents trifluoromethyl or chlorodifluoromethyl. In equation (1),
The substituted acetal compound or a salt thereof according to claim ³ , wherein X ³ represents a hydrogen atom. In equation (1),
The substituted acetal compound or a salt thereof according to claim 1, wherein R ¹ represents a hydrogen atom. In equation (1),
X ¹ represents a halogen atom, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ haloalkoxy or C ₁ -C ₄ haloalkylthio,
The substituted acetal compound or a salt thereof according to claim 5, wherein X ³ represents a hydrogen atom, a halogen atom, C ₁ -C ₄ haloalkyl or C ₁ -C ₄ haloalkoxy. In equation (1),
X ² is a halogen atom, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ haloalkoxy or C ₁ -C ₄ haloalkylthio,
X ³ represents a hydrogen atom, a fluorine atom, a C ₁ -C ₄ haloalkyl or a C ₁ -C ₄ haloalkoxy,
The substituted acetal compound or a salt thereof according to claim 6, wherein X represents trifluoromethyl or chlorodifluoromethyl. In equation (1),
The substituted acetal compound or a salt thereof according to claim 7, wherein X ³ represents a hydrogen atom. Formula (2):

[Wherein, A ¹ , A ² , A ³ and A ⁴ each independently represent N or CY,
R is, C ₁ -C ₆ alkyl, halogen atom, cyano, ^{_{nitro, -NH 2, -N (R 5}} ) R 4, -OH, -OR 3, benzyloxy, -OSO ₂ R ^3, phenylsulfonyloxy, (Z) phenylsulfonyloxy substituted by _{p1, -C (O) OH,} -C (O) OR 3, -C (O) NH 2, -C (O) N (R 1b) R 1a, -C (S) N (R ^1b ) R ^1a , -LQ, -LN (R ^1c ) R ^1d , C ₁ -C ₆ alkylsulfonyl, C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ alkylthio, -S (O ) represents a substituent selected from _r -L ² -Q ² or D-1 to D-50,
R ³ represents C ₁ -C ₆ alkyl, C ₁ -C ₄ alkoxy (C ₁ -C ₄ ) alkyl, C ₁ -C ₆ haloalkyl or C ₁ -C ₃ haloalkoxy (C ₁ -C ₃ ) haloalkyl. ,
Y is a hydrogen atom, a halogen atom, cyano, nitro, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₆ alkylthio, C _{1 to} C ₆ haloalkylthio, C _{1 to} C ₆ alkylsulfonyl, C _{1 to} C ₆ haloalkylsulfonyl, —NH ₂ or —N (R ⁵ ) R ⁴ , each Y may be the same as each other or They may be different,
Two adjacent Ys may be joined together to form A ⁸ = A ⁹ -A ¹⁰ = A ¹¹
A ⁸ , A ⁹ , A ¹⁰ and A ¹¹ each independently represent N or CY ¹
Y ¹ is a hydrogen atom, a halogen atom, cyano, nitro, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ haloalkylthio, C ₁ -C ₆ alkylsulfonyl, C ₁ -C ₆ haloalkylsulfonyl, —NH ₂ or —N (R ⁵ ) R ⁴ , each Y ¹ may be the same as each other Or they may be different from each other,
R ⁴ is, C ₁ -C ₆ alkyl, -CHO, C ₁ ~C ₆ alkyl carbonyl, C ₁ -C ₆ haloalkylcarbonyl, C ₁ -C ₆ alkoxycarbonyl, C ₁ -C ₆ alkylthiocarbonyl, C ₁ -C ₆ alkoxythiocarbonyl, C ₁ -C ₆ alkyl dithio carbonyl, represents C ₁ -C ₆ alkylsulfonyl or C ₁ -C ₆ haloalkylsulfonyl,
R ⁵ represents a hydrogen atom or C ₁ -C ₆ alkyl,
R ^1a is, C ₁ -C ₆ alkyl, C ₁ -C ₆ alkyl optionally substituted by R ^8, condensed which may C ₃ even though -C ₆ cycloalkyl with the benzene ring, C ₃ -C ₆ alkenyl , C ₃ -C ₆ haloalkenyl, C ₃ -C ₆ ^{alkynyl, -N (R 11) R 10} , -C (O) OR 9, -C (O) NH 2, -C (O) NHR 9, - C (R ⁷ ) = NOR ⁶ , phenyl, phenyl substituted by (Z) _p1 , D-5, D-7, D-10, D-11, D-12, D-14, D-15, D -18, D-31, D-32, D-42, D-43, D-45, D-46, D-48, E-1, E-2, E-3, E-4 or E-7 Represents
R ^1b is a hydrogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₄ alkoxy (C ₁ -C ₄ ) alkyl, cyano (C ₁ -C ₆ ) alkyl, C ₃ -C ₆ alkynyl, -C (O ) Represents R ⁹ or -C (O) OR ⁹ ;
Alternatively, R ^1b may form a C _{2 to} C ₆ alkylene chain together with R ^1a to form a 3- to 7-membered ring together with the nitrogen atom to which R ^1b is bonded. It may contain one oxygen atom, sulfur atom or nitrogen atom,
L represents -C (R ^2a ) (R ^2b )-, -C (R ^2a ) (R ^2b ) CH ₂ -or -CH ₂ C (R ^2a ) (R ^2b )-,
Q represents a halogen atom, cyano, nitro or G-1 to G-5,
R ^1c is a hydrogen atom, -C (O) R ^3a , -C (O) OR ^3a , -C (O) SR ^3a , -C (O) N (R ^3b ) R ^3a , -C (S) N (R ^3b ) R ^3a or -S (O) ₂ R ^3a
R ^1d is a hydrogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₄ alkoxy (C ₁ -C ₄ ) alkyl, C ₁ -C ₄ haloalkoxy (C ₁ -C ₄ ) alkyl, C ₁ -C ₄ alkylthio (C ₁ ~C ₄₎ alkyl, C ₁ -C ₄ alkylsulfonyl (C ₁ ~C ₄₎ alkyl, cyano (C ₁ ~C ₆₎ alkyl, C ₃ -C ₆ cycloalkyl , C ₃ -C ₆ cycloalkyl (C ₁ ~C ₄₎ alkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ ^{alkynyl, -C (O) R 3c,} -C (O) OR 3c, -C ( O) SR ^3c, represent a C ₁ -C ₆ haloalkylthio or C ₁ -C ₆ alkylsulfonyl,
Alternatively, R ^1c together with R ^1d forms a C _{4 to} C ₆ alkylene chain, thereby indicating that a 5 to 7 membered ring may be formed with the nitrogen atom to which R ^1c is bonded. oxygen atom may contain one sulfur atom or a nitrogen atom, and C ₁ -C ₆ alkyl group, -CHO group, C ₁ -C ₆ alkylcarbonyl group, C ₁ -C ₆ haloalkylcarbonyl group, C ₁ ~ C ₆ alkoxycarbonyl group, C ₁ -C ₆ haloalkoxycarbonyl group, C ₁ -C ₆ alkylaminocarbonyl group, C ₁ -C ₆ haloalkylaminocarbonyl group, oxo group or thioxo group may be optionally substituted ,
R ^2a represents a hydrogen atom, cyano, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxycarbonyl, -C (O) NH ₂ or -C a (S) NH _2,
R ^2b represents a hydrogen atom or C ₁ -C ₆ alkyl, or R ^2a and R ^2b together form a C ₂ -C ₅ alkylene chain to form 3- It represents that a 6-membered ring may be formed, and this alkylene chain may contain 1 to 3 oxygen atoms, sulfur atoms or nitrogen atoms,
R ^3a is C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, (C ₁ -C ₄ ) alkyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ halocyclo optionally substituted by R ^4a alkyl, E-1, E-2 , E-4, C 2 ~C 6 alkenyl, C ₂ -C ₆ haloalkenyl, C ₂ -C ₆ alkynyl, phenyl, phenyl substituted by (V) _p1, D- 3, D-4, D-12 to D-14, D-42 or D-43,
R ^3b represents a hydrogen atom or C ₁ -C ₆ alkyl,
R ^3c is a hydrogen atom, C ₁ -C ₄ alkyl, (C ₁ -C ₄ ) alkyl, C ₁ -C ₄ haloalkyl, C ₃ -C ₆ cycloalkyl (C ₁ -C) optionally substituted by R ^3d ₄₎ an alkyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl, phenyl, phenyl substituted by R ^14a, a D-42, D-43 or D-44,
R ^3d represents cyano, nitro, C ₁ -C ₄ alkoxy, C ₁ -C ₆ alkoxycarbonyl, S (O) _r R ^5a , phenyl, D-42, D-43 or D-44,
G-1 to G-5 each represent the following structure,

R ^4a represents cyano, nitro, C ₃ -C ₆ cycloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₆ alkoxycarbonyl, S (O) _r R ^5a , D-42 or D-43,
R ^5a represents C ₁ -C ₄ alkyl,
V represents a halogen atom, cyano, nitro, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, -OH, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, C ₁ -C ₆ alkylsulfonyloxy , C ₁ -C ₆ haloalkylsulfonyloxy, 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, -NH _2, C _{1 ~C 6} alkyl amino, di (C ₁ -C ₆ alkyl) amino, C ₁ -C _{6 alkoxycarbonyl, -C (O) NH 2,} C 1 ~C ₆ alkylaminocarbonyl, C ₁ -C ₆ haloalkylcarbonyl aminocarbonyl, di (C ₁ -C ₆ alkyl) _{aminocarbonyl, -C (S) NH 2,} -S (O) 2 NH 2, C 1 ~C 6 alkyl amino represents sulfonyl or di (C ₁ -C ₆ alkyl) aminosulfonyl, p1 indicates an integer of 2 or more Come, each V is may be the or different from each other the same as each other,
Furthermore, if the two V are adjacent, the two V adjacent able to form a -OCH ₂ O-or -OCH ₂ CH ₂ O-, 5-membered together with the carbon atom to which each of the two V binds A ring or a 6-membered ring may be formed, and at this time, a hydrogen atom bonded to each carbon atom forming the ring may be optionally substituted with a halogen atom,
R ⁶ is a hydrogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ halocycloalkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ haloalkenyl, C ₃ -C ₆ alkynyl, C ₃ -C ₆ haloalkynyl, phenyl, phenyl substituted by _{(Z) p1, D-42} , D-45~D-49, E-1~E-4 or Represents E-7,
R ⁷ is a hydrogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy (C ₁ ~C ₆₎ alkyl, C ₁ -C ₆ alkylthio (C ₁ ~C ₆₎ alkyl , C ₃ -C ₆ cycloalkyl or phenyl,
R ⁸ is a halogen atom, cyano, amino, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ halocycloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ haloalkylthio, C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ haloalkylsulfinyl, C ₁ -C ₆ alkylsulfonyl, C ₁ -C ₆ ^{haloalkylsulfonyl, -C (O) R 14,} -C (O) OR ¹⁴ , -C (O) NH ₂ , -C (O) N (R ¹⁵ ) R ¹⁴ , -C (S) NH ₂ , -C (S) N (R ¹⁵ ) R ¹⁴ , -C (R ⁷ ) = NOR ⁶ , phenyl, phenyl substituted by (Z) _p1 , D-1 to D-50 or E-1 to E-8,
D-1 to D-50 each represents an aromatic heterocyclic ring represented by the following structural formula,

Z is a halogen atom, cyano, nitro, amino, C ₁ -C ₆ alkyl, optionally substituted by R ¹⁶ (C ₁ ~C ₆₎ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ haloalkylthio, C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ haloalkylsulfinyl, C ₁ -C ₆ alkylsulfonyl, C ₁ ~ C ₆ haloalkylsulfonyl, C ₁ -C _{6 alkoxycarbonyl, -C (O) NH 2,} -C (S) NH 2, -S (O) 2 NH 2, -C (O) N (R 18) R 17 , -C (S) N (R ¹⁸ ) R ¹⁷ , C ₁ -C ₆ alkylaminosulfonyl or di (C ₁ -C ₆ alkyl) aminosulfonyl, p1, p2, p3 or p4 represents an integer of 2 or more When represented, each Z may be the same as or different from each other,
E-1 to E-8 each represent a heterocyclic ring represented by the following structural formula;

R ⁹ is C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy (C ₁ -C ₄ ) alkyl, C ₁ -C ₆ alkylthio (C ₁ -C ₄ ) alkyl, C ₃ -C ₈ cycloalkyl represents C ₃ -C ₆ alkenyl or C ₃ -C ₆ alkynyl,
R ¹⁰ is C ₁ -C ₆ haloalkyl, -C (O) R ¹⁴ , -C (O) OR ¹⁴ , phenyl, phenyl substituted by (Z) _p1 , D-3, D-4, D-18 , D-42, D-45, D-46, D-48 or D-49,
R ¹¹ represents a hydrogen atom, C ₁ -C ₆ alkyl or C ₃ -C ₆ alkynyl,
R ¹² represents C ₁ -C ₆ alkyl, phenyl or phenyl substituted by (Z) _{p 1}
R ¹³ represents C ₁ -C ₄ alkyl, and when q2, q3 or q4 represents an integer of 2 or more, each R ¹³ may be the same as or different from each other, When two R ¹³ are substituted on the same carbon atom, the two R ¹³ together may form an oxo;
R ¹⁴ is C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₃ -C ₆ cycloalkyl (C ₁ -C ₄ ) alkyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₆ alkoxy (C ₁ -C ₆₎ represents alkyl, hydroxy (C ₁ ~C ₆₎ alkyl, phenyl, phenyl substituted by R ^14a, C ₃ ~C ₆ haloalkenyl, a C ₃ -C ₆ alkenyl or C ₃ -C ₆ alkynyl ,
R ^14a is a halogen atom, cyano, nitro, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, C ₁ -C ₆ alkylthio, C ₁ ~ C ₆ haloalkylthio, C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ haloalkylsulfinyl, C ₁ -C ₆ alkylsulfonyl, C ₁ -C ₆ haloalkylsulfonyl, C ₁ -C ₆ alkoxycarbonyl, -C (O) _{NH 2, -S (O) 2} NH 2, C 1 ~C 6 alkyl aminosulfonyl or di (C ₁ -C ₆ alkyl) represent aminosulfonyl,
R ¹⁵ represents a hydrogen atom or C ₁ -C ₆ alkyl,
R ¹⁶ is, -OH, C ₁ -C ₄ alkoxy or C ₁ -C ₄ alkylthio,
R ¹⁷ is a hydrogen atom, C ₁ -C ₆ alkyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ haloalkenyl, C ₃ -C ₆ alkynyl, -C (R ⁵ ) = NOR ¹⁹ , -C (O) OR ¹⁹ , -C (O) NH ₂ , -C (O) N (R ⁵ ) R ¹⁹ , -C (O) NHC (O) R ¹⁹ , -C (O) Represents N (R ⁵ ) C (O) OR ¹⁹ , -N (R ²¹ ) R ²⁰ or phenyl;
R ¹⁸ represents a hydrogen atom, C ₁ -C ₆ alkyl or C ₃ -C ₆ alkynyl,
R ¹⁹ represents C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl or C ₂ -C ₆ alkenyl,
R ²⁰ represents C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxycarbonyl, phenyl, phenyl substituted by R ^20a , D-42-D-46 or D-47;
R ^20a represents a halogen atom, cyano, nitro, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, a C ₁ -C ₆ alkoxy or C ₁ -C ₆ alkylsulfonyl,
R ²¹ represents a hydrogen atom, C ₁ -C ₆ alkyl, C ₃ -C ₆ alkenyl or C ₃ -C ₆ alkynyl,
L ² represents a single bond or a C ₁ -C ₆ alkylene chain,
Q ² is, C ₁ -C ₆ haloalkyl, C ₂ -C ₆ ^{alkynyl, -N (R 23) R 22} , -C (O) N (R 23) R 22, phenyl, substituted by (Z) _p1 Represents phenyl, D-18 to D-20, D-42 to D-46 or D-47;
R ²² is substituted by C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl, phenyl or (Z) _p1 Represents phenyl,
R ²³ represents a hydrogen atom or C ₁ -C ₆ alkyl,
p1 represents an integer of 1 to 5,
p2 represents an integer of 0 to 4,
p3 represents an integer of 0 to 3,
p4 represents an integer of 0 to 2,
p5 represents an integer of 0 or 1,
q2 represents an integer of 0 to 5,
q3 represents an integer of 0 to 7,
q4 represents an integer of 0 to 9,
r represents an integer of 0 to 2;
t represents an integer of 0 or 1. ]
A compound represented by formula (1) according to claim 1:

[Wherein, X ¹ , X ² , X ³ , X and R ¹ represent the same meaning as described in claim 1. ]
By reacting with a compound represented by formula (3):

[Wherein, A ¹ , A ² , A ³ , A ⁴ , X ¹ , X ² , X ³ , R and X are the same as the contents described in the compounds represented by formula (1) and formula (2). Represents meaning. ]
The manufacturing method of the substituted hydroxypropanone compound represented by these. R is, C ₁ -C ₄ alkyl, halogen atom, cyano, ^{_{nitro, -NH 2, -N (R 5}} ) R 4, -OH, -OR 3, ^{_{benzyloxy, -OSO 2 R 3, (Z}} ) p1 Phenylsulfonyloxy substituted by -C (O) OH, -C (O) OR ³ , -C (O) NH ₂ , -C (O) N (R ^1b ) R ^1a , -C (S) N (R ^1b ) R ^1a , -LQ, -LN (R ^1c ) R ^1d or -S (O) _r -L ² -Q ² is D-11 to D-14, D-21 to D-24, D- Represents 36-D-40 or D-41,
Y is a hydrogen atom, a halogen atom, cyano, nitro, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ haloalkylsulfonyl or -N (R ⁵⁾ R ⁴ Each Y may be the same as or different from each other;
Two adjacent Ys may be joined together to form C = CC = C,
R ⁴ is, C ₁ -C ₄ represents alkyl, -CHO, C ₁ -C ₄ alkylcarbonyl, a C ₁ -C ₄ alkoxycarbonyl or C ₁ -C ₄ alkylsulfonyl,
R ⁵ represents a hydrogen atom,
R ^1a is C ₁ -C ₆ alkyl, C ₁ -C ₄ alkyl optionally substituted by R ⁸ , -N (R ¹¹ ) R ¹⁰ , -C (O) OR ⁹ , -C (O) NH ₂ , -C (O) NHR ⁹ , -C (R ⁷ ) = NOR ⁶ , phenyl, phenyl substituted by (Z) _p1 , D-5, D-7, D-10, D-11, D-12 , D-14, D-15, D-18, D-31, D-32, D-42, D-43, D-45, D-46, D-48, E-1 or E-7 ,
R ^1b represents a hydrogen atom, C ₁ -C ₆ alkyl, —C (O) R ⁹ or —C (O) OR ⁹ ;
R ^1d is a hydrogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₄ alkoxy (C ₁ -C ₄ ) alkyl, C ₁ -C ₄ haloalkoxy (C ₁ -C ₄ ) alkyl, C ₁ -C ₄ alkylthio (C ₁ ~C ₄₎ alkyl, C ₁ -C ₄ alkylsulfonyl (C ₁ ~C ₄₎ alkyl, cyano (C ₁ ~C ₆₎ alkyl, C ₃ -C ₆ cycloalkyl , C ₃ -C ₆ cycloalkyl (C ₁ ~C ₄₎ represents alkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl, -C a (O) oR ^3c or -C (O) R ^3c,
R ^2a represents a hydrogen atom, cyano, C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
R ^2b represents a hydrogen atom or C ₁ -C ₆ alkyl,
R ⁶ is a hydrogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ halocycloalkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ haloalkenyl, represents C ₃ -C ₆ alkynyl or C ₃ -C ₆ haloalkynyl,
R ⁸ is fluorine atom, chlorine atom, bromine atom, cyano, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ halocycloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, -C ( O) R ¹⁴ , -C (O) OR ¹⁴ , -C (O) NH ₂ , -C (O) N (R ¹⁵ ) R ¹⁴ , -CH = NOR ⁶ , phenyl, substituted by (Z) _p1 Represents phenyl, D-14, D-19, D-31, D-32, D-36, D-42 or E-5;
R ¹⁰ is C ₁ -C ₆ haloalkyl, -C (O) R ¹⁴ , -C (O) OR ¹⁴ , phenyl, phenyl substituted by (Z) _p1 , D-18, D-42 or D-45 Represents
R ¹¹ represents a hydrogen atom,
R ¹³ represents C ₁ -C ₄ alkyl, and when q2, q3 or q4 represents an integer of 2 or more, each R ¹³ may be the same as or different from each other, When two R ¹³ are substituted on the same carbon atom, the two R ¹³ together may form an oxo;
R ¹⁴ is C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₃ -C ₆ cycloalkyl (C ₁ -C ₄ ) alkyl, C ₃ -C ₆ cycloalkyl, C ₁ -C ₆ alkoxy (C ₁ -C ₆₎ represents alkyl, C ₃ -C ₆ haloalkenyl, a C ₃ -C ₆ alkenyl or C ₃ -C ₆ alkynyl,
R ¹⁷ is C ₁ -C ₆ alkyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ haloalkenyl, C ₃ -C ₆ alkynyl, -C (O) OR ¹⁹ ,- C (O) NH ₂ , -C (O) N (R ⁵ ) R ¹⁹ , -C (O) NHC (O) R ¹⁹ , -C (O) N (R ⁵ ) C (O) OR ¹⁹ ,- Represents N (R ²¹ ) R ²⁰ or phenyl;
R ¹⁸ represents a hydrogen atom,
R ²¹ represents a hydrogen atom,
Q ² is C ₁ -C ₆ haloalkyl, C ₂ -C ₆ alkynyl, -N (R ²³ ) R ²² , -C (O) N (R ²³ ) R ²² , D-42-D-46 or D- 47
R ²³ represents a hydrogen atom,
p1 represents an integer of 1 or 2,
p2 represents an integer of 0 or 1,
p3 represents an integer of 0 or 1,
p4 represents an integer of 0 or 1,
q2 represents an integer of 0, 1 or 2;
q3 represents an integer of 0, 1 or 2,
q4 represents an integer of 0, 1 or 2,
t represents an integer of 0 or 1,
X ¹ represents a halogen atom, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ haloalkoxy or C ₁ -C ₄ haloalkylthio,
X ³ represents a hydrogen atom, a halogen atom, C ₁ -C ₄ haloalkyl or C ₁ -C ₄ haloalkoxy,
X represents trifluoromethyl or chlorodifluoromethyl,
The manufacturing method of Claim 9. R is, C ₁ -C ₄ alkyl, halogen atom, cyano, _{nitro, -NH 2, -OH, -C (} O) OH, -C (O) OR 3, -C (O) NH 2, -C ( O) N (R ^1b ) R ^1a , -LQ, -LN (R ^1c ) R ^1d , C ₁ -C ₄ alkylsulfonyl or -S (O) _r -L ² -Q ²
R ³ represents C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl,
Y is a hydrogen atom, a halogen atom, cyano, nitro, C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl, each Y may be the even or different from each other the same as each other,
Two adjacent Ys may be joined together to form C = CC = C,
R ^1a is, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkyl optionally substituted by ^{R 8, -N (R 11)} R 10, -C (O) OR 9, -C (O) NHR 9 ^{, -C (R 7) = NOR} 6, represents phenyl, phenyl, D-42, D-43 , D-45, D-46 or D-48 substituted by (Z) _p1,
L represents -C (R ^2a ) (R ^2b )-
Q represents a halogen atom, cyano, nitro, G-1, G-2 or G-4,
R ^1c represents -C (O) R ^3a , -C (O) OR ^3a or -C (O) N (R ^3b ) R ^3a ,
R ^1d is a hydrogen atom, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy (C ₁ -C ₄ ) alkyl, C ₁ -C ₄ haloalkoxy (C ₁ -C ₄ ) represents alkyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ alkenyl or C ₃ -C ₆ alkynyl,
R ^2b represents a hydrogen atom,
R ^3a is C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, (C ₁ -C ₄ ) alkyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ halocyclo optionally substituted by R ^4a Represents alkyl, phenyl or phenyl substituted by (V) _p1 ,
R ^3b represents a hydrogen atom,
R ^4a represents cyano, nitro, C ₃ -C ₆ cycloalkyl, S (O) _r R ^5a , D-42 or D-43,
V represents a halogen atom, cyano, nitro, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, C ₁ -C ₆ alkylsulfonyl, C ₁ ~ C ₆ haloalkylsulfonyl, C ₁ -C ₆ alkoxycarbonyl, C ₁ -C ₆ alkylaminosulfonyl or di (C ₁ -C ₆ alkyl) aminosulfonyl, and when p ₁ represents an integer of 2, each V is They may be the same or different from each other,
R ⁶ represents C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₃ -C ₆ alkenyl or C ₃ -C ₆ alkynyl,
R ⁷ represents a hydrogen atom or C ₁ -C ₄ alkyl,
R ⁸ is a fluorine atom, a chlorine atom, cyano, -C (O) OR ¹⁴ , -C (O) N (R ¹⁵ ) R ¹⁴ , phenyl, phenyl substituted by (Z) _p1 , D-19, D -42 or E-5,
Z is a fluorine atom, a chlorine atom, a bromine atom, cyano, nitro, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ represents alkylsulfonyl, C ₁ -C ₄ alkoxycarbonyl, -C a (O) NH ₂ or C ₁ -C ₄ alkylaminosulfonyl, when p1 represents an integer 2, each Z is They may be the same or different from each other,
R ⁹ represents C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₃ -C ₆ alkenyl or C ₃ -C ₆ alkynyl,
R ¹⁴ is C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₃ -C ₆ cycloalkyl (C ₁ -C ₄ ) alkyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ haloalkenyl, C ₃ -C ₆ alkenyl or C ₃ -C ₆ alkynyl,
L ² represents a single bond, methylene, ethylidene, ethylene or trimethylene,
Q ² represents C ₁ -C ₄ haloalkyl, C ₂ -C ₆ alkynyl or -C (O) N (R ²³ ) R ²² ,
R ²² represents C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ alkenyl or C ₃ -C ₆ alkynyl,
X ² represents a hydrogen atom, a halogen atom, C ₁ -C ₄ haloalkyl or C ₁ -C ₄ haloalkoxy,
X ³ represents a hydrogen atom, a fluorine atom or a chlorine atom,
The manufacturing method of Claim 10. A ¹ and A ² represent a carbon atom,
R is, C ₁ -C ₄ represents alkyl, a fluorine atom, a chlorine atom, a bromine atom, a -C (O) OH, -C ( O) OR 3 or ^{-C (O) N (R 1b} ) R 1a,
R ³ represents C ₁ -C ₄ alkyl,
Y is a hydrogen atom, a fluorine atom, a chlorine atom, nitro, C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl, each Y may be the even or different from each other the same as each other,
Two adjacent Ys may be joined together to form C = CC = C,
R ^1a is, C ₁ -C ₄ alkyl, C optionally substituted by R ⁸ ₁ -C ₄ alkyl, phenyl, (Z) phenyl substituted by _{p1, D-42, D-} 43, D-45, Represents D-46 or D-48,
R ^1b represents a hydrogen atom,
R ⁸ is a fluorine atom, cyano, -C (O) OR ¹⁴ , -C (O) N (R ¹⁵ ) R ¹⁴ , phenyl, phenyl substituted by (Z) _p1 , D-19, D-42 or Represents E-5,
When Z is a fluorine atom, a chlorine atom, a bromine atom, cyano, nitro, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl or C ₁ -C ₄ haloalkoxy, where p1 represents an integer 2, respectively Z may be the same as or different from each other,
R ¹⁴ represents C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₃ -C ₆ cycloalkyl (C ₁ -C ₄ ) alkyl or C ₃ -C ₆ cycloalkyl,
R ¹⁵ represents a hydrogen atom,
q2 represents an integer of 0 or 1,
t represents an integer of 0;
X ² represents a halogen atom, C ₁ -C ₄ haloalkyl or C ₁ -C ₄ haloalkoxy,
X represents trifluoromethyl,
R ¹ represents a hydrogen atom, methyl or ethyl,
The manufacturing method of Claim 11.