OA17118A

OA17118A - Pest control composition including novel iminopyridine derivative

Info

Publication number: OA17118A
Application number: OA1201400392
Authority: OA
Inventors: Ryo Horikoshi; Yasumichi Onozaki; Satoshi Nakamura; Masahiro Nomura; Makoto Matsumura; Masaaki Mitomi
Original assignee: Meiji Seika Pharma Co., Ltd.
Priority date: 2012-02-19
Filing date: 2013-02-27
Publication date: 2016-03-28

Abstract

Provided is a pest control composition containing a novel iminopyridine derivative and other pest control agents. Provided is a pest control composition containing an iminopyridine derivative represented by the following formula (I)

Description

The présent invention relates to a pest control composition containing a novel imlnopyridine dérivative and at least one of other pest control agents. [Background Art]

Although numerous pest control agents hâve been discovered so far, the development of novel drugs which has high safety is still required in view of the problem of réduction in drug sensitivity, the Issue of long-term effîcacy, safety to workers or safety in terms of environmental impacts. Further, in agriculture, In order to achieve a réduction In iabor for the pest control work, it is general to mix a plurality of components of a chemical for pest control and treat seeds or farm products during the growing seedling period with the chemical, and under these circumstances, it ls required to use a long-term resldual effîcacy type chemical having penetrating and migrating property. In addition, it is also possible to solve problems such as scattering of a chemical to the surrounding environment outside agriculture! land or exposure to a person who performs pest control by seed treatment or treatment during the growing seedling period.

Européen Patent Application Lald-Open No. 432600(PTL1) discloses a plurality of compounds having the same ring structure as that of a compound represented by Formula (I), but the compounds are used as herbicides and there is no description about pest control.

Japanese Patent Application Laid-Open (JP-A) No. 5-78323(PTL2) discloses the structural formula of N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2trifluoroacetamide (Compound No. 3 in Table 1 of JP-A No. 5-78323), but fails to disclose a préparation method thereof and the compound is not induded in a list of the group of compounds that are recognized to hâve pest control activity (Tables 2 and 3 of JP-A No. 578323).

European Patent Application Lald-Open No. 268915(PTL3) discloses the structural formula of N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamlde (Example No. 12 in Table 7 of European Patent Application Laid-Open No. 268915), but fails to disclose a préparation method thereof and the Example does not include the compound as an example of the compounds having pest control activity.

Chemische Berichte (1955), 88,1103-8(NPL1) discloses a plurality of compounds having a ring structure similar to that of a compound represented by Formula (I) to be described below, but the compounds are disclosed only as synthetic intermediates.

European Patent Application Laid-Open No. 259738(PTL4) discloses a plurality of compounds having a ring structure similar to that of a compound represented by Formula (I), but fails to disclose or suggest a compound having a trifluoroacetic acid imino structure.

Furthermore, these documents do not descrlbe pest control activity when the novel iminopyridine dérivative of the présent Invention is mlxed with another pest control agent.

[Citation List] [Patent Literature] [PTL 1] European Patent Application Laid-Open No. 432600 [PTL 2] Japanese Patent Application Laid-Open (JP-A) No. 5-78323 [PTL 3] European Patent Application Lald-Open No. 268915 [PTL 4] European Patent Application Laid-Open No. 259738 [Non Patent Literature] [NPL 1] Chemische Berichte (1955), 88, 1103-8 [Summary of Invention] [Technicai Problem]

The présent invention Is contrived to provide a novel pest control agent to solve problems which chemicals In the related art hâve, such as réduction in drug sensitivity, long-term efficacy, safety during the use thereof and the like in the field of pest control.

[Solution to Probiem] ln order to solve the problème, the présent Inventors hâve Intenslvely studied, and as a resuit, hâve found that a novei Imlnopyridine derlvative represented by Formula (I) has excellent pest control effects against pests and discovered a composition showing excellent pest control effects by containing these novel Imlnopyridine dérivatives and at least one of other pest control agents, compared to when a single agent is used, and a use method thereof. The présent Invention is based on the finding.

Therefore, an object of the présent Invention Is to provide a pest control composition prepared by containing at least one of a novel imlnopyridine dérivative represented by the foliowing Formula (I) or acid addition salts thereof and at least one of other pest control agents, which Is used In a low dose and shows excellent pest control effects against a wide range of pests.

(1) There Is provided a pest contrai composition containing at least one of a novel Imlnopyridine derlvative represented by the foliowing Formula (I) or acid addition salts thereof as an active Ingrédient and at least one of other pest control agents: [Chemical Formula 1]

(I) [in the formula, Ar represents a phenyl group which may be substituted, a 5- to 6membered heterocycle which may be substituted, or a 4- to 10-membered heterocycloaikyl group,

A represents a heterocycle having a 5* to 10-membered unsaturated bond including one or more nitrogen atoms, and has an imlno group substituted with an R group at a position adjacent to the nitrogen atom présent on the cycle,

Y represents a hydrogen atom, a halogen atom, a hydroxyl group, a C1 to C6 alkyl group which may be substituted with a halogen atom, a C1 to C6 alkyloxy group which may be substituted with a halogen atom, a cyano group, or a nitro group, and

R represents any one of groups represented by the following Formuiae (a) to (e), (y) or (z).

[Chemical Formula 2]

—C-R, il ¹	—C-0R₂	—c-r₃ Il ^J	—c-r₅ Il ³	—c-r₇ II	n¹ ,^R*
O	0	s	N 1	N 1	-P-Y₂	01
			R4	ORe	1 Y₂„	Π
(a)	(b)	(c)	(d)	(θ)	(y) Ry	(Z)

[here, R1 represents a hydrogen atom, a substituted C1 to C6 alkyl group, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, or a pentafluorophenyl group,

R2 represents a C1 to C6 alkyl group substituted with a halogen atom, an unsubstituted C3 to C6 branched or cyclic alkyl group, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to C10) aryl group, a substituted or unsubstituted 5- to 10membered heterocycle, or a substituted or unsubstituted benzyl group,

R3 represents a C1 to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to C10) aryl group, a substituted or unsubstituted (C6 to C10) aryl (C1 to C6) alkyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkenyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkynyl group, a substituted or unsubstituted phenoxy (C1 to C6) alkyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkenyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkynyl group, a substituted or unsubstituted 5- to 10-membered heterocycle, a substituted or unsubstituted 5- to 10membered heterocycle (C1 to C6) alkyl group, a substituted or unsubstituted 5- to 10 membered heterocycle (C2 to C6) alkenyl group, a substituted or unsubstituted 5- to 10membered heterocycle (C2 to 06) alkynyl group, a (C1 to 04) alkoxy (C1 to 05) alkyl group, a (C1 to C4) alkoxy (02 to 05) alkenyl group, a (01 to 04) alkoxy (02 to 05) alkynyl group, a (01 to C4) alkylthio (C1 to 05) alkyl group, a (C1 to 04) alkylthio (02 to 05) alkenyl group, or a (C1 to 04) alkylthîo (02 to 05) alkynyl group,

R4 represents a hydrogen atom, a formyl group, a C1 to 06 alkyl group which may be substituted, a 02 to 06 alkenyl group which may be substituted with a halogen atom, a 02 to 06 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (06 to 010) aryl group, a substituted or unsubstituted (06 to C10) aryl (C1 to 06) alkyl group, a substituted or unsubstituted (06 to C10) aryl (02 to 06) alkenyl group, a substituted or unsubstituted (06 to C10) aryl (02 to 06) alkynyl group, a substituted or unsubstituted phenoxy (C1 to 06) alkyl group, a substituted or unsubstituted phenoxy (02 to 06) alkenyl group, a substituted or unsubstituted phenoxy (02 to 06) alkynyl group, a substituted or unsubstituted 5- to 10-membered heterocycle, a substituted or unsubstituted 5- to 10membered heterocycle (C1 to 06) alkyl group, a substituted or unsubstituted 5- to 10membered heterocycle (02 to 06) alkenyl group, a substituted or unsubstituted 5- to 10membered heterocycle (02 to 06) alkynyl group, a (C1 to 04) alkoxy (C1 to 05) alkyl group, a (C1 to 04) alkoxy (02 to 05) alkenyl group, a (C1 to 04) alkoxy (02 to 05) alkynyl group, a (01 to 04) alkylthio (C1 to 05) alkyl group, a (01 to 04) alkylthio (02 to 05) alkenyl group, a (01 to 04) alkylthio (02 to 05) alkynyl group, or a group represented by any of the following Formulae (f) to (n) [Chemical Formula 3]

II

-Ç-R4.	-C-OR^ -	-S-R_4c
° (f)	° (g)	° Φ)
—C“R_4d H	- C-OR4d	-C-SR_4d -	-Ç-SR_4d
s ...	S	S	O
(i)	û)	(k)	(i)

—C—N Il *	—C—N
o R4f	(m) s &4f	(n)

here, R4a, R4b and R4c represent a C1 to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to C10) aryl group, a substituted or unsubstituted (C6 to C10) aryl (C1 to C6) alkyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkenyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkynyl group, a substituted or unsubstituted phenoxy (C1 to C6) alkyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkenyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkynyl group, a substituted or unsubstituted 5- to 10-membered heterocycle group, a substituted or unsubstituted 5- to 10-membered heterocycle (C1 to C6) alkyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkenyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkynyl group, a (C1 to C4) alkoxy (C1 to C5) alkyl group, a (C1 to C4) alkoxy (C2 to C5) alkenyl group, a (C1 to C4) alkoxy (C2 to C5) alkynyl group, a (C1 to C4) alkytthio (C1 to C5) alkyl group, a (C1 to C4) alkylthlo (C2 to C5) alkenyl group, or a (C1 to C4) alkytthio (C2 to C5) alkynyl group,

R4d représente a C1 to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to C10) aryl group, or a substituted or unsubstituted 5- to 10-membered heterocycle, and

R4e and R4f each independently represent a hydrogen atom, a C1 to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a haiogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to C10) aryl group, or a substituted or unsubstituted 5- to 10-membered heterocycle,

R5 represents a C1 to C6 alkyl group which may be substituted with a halogen atom, a C1 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to C10) aryl group, a substituted or unsubstituted (C6 to C10) aryl (C1 to C6) alkyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkenyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkynyl group, a substituted or unsubstituted phenoxy (C1 to C6) alkyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkenyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkynyl group, a substituted or unsubstituted 5- to 10-membered heterocycle, a substituted or unsubstituted 5- to 10membered heterocycle (C1 to C6) alkyl group, a substituted or unsubstituted 5- to 10membered heterocycle (C2 to C6) alkenyl group, a substituted or unsubstituted 5- to 10membered heterocycle (C2 to C6) alkynyl group, a (C1 to C4) alkoxy (C1 to C5) alkyl group, a (C1 to C4) alkoxy (C2 to C5) alkenyl group, a (C1 to C4) alkoxy (C2 to C5) alkynyl group, a (C1 to C4) alkylthio (C1 to C5) alkyl group, a (C1 to 04) alkylthio (02 to 05) alkenyl group, or a (C1 to 04) alkylthio (02 to 05) alkynyl group,

R6 represents a hydrogen atom, a formyl group, a 0,0'-C1 to 04 alkyl phosphoryl group, a C1 to C18 alkyl group which may be substituted, a 02 to 06 alkenyl group which may be substituted with a halogen atom, a 02 to 06 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (06 to C10) aryl group, a substituted or unsubstituted (06 to C10) aryl (01 to 06) alkyl group, a substituted or unsubstituted (06 to C10) aryl (02 to 06) alkenyl group, a substituted or unsubstituted (06 to C10) aryl (02 to 06) alkynyl group, a substituted or unsubstituted phenoxy (01 to 06) alkyl group, a substituted or unsubstituted phenoxy (02 to 06) alkenyl group, a substituted or unsubstituted phenoxy (02 to 06) alkynyl group, a substituted or unsubstituted 5- to 10-membered heterocycle, a substituted or unsubstituted 5- to 10-membered heterocycle (C1 to C6) alkyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkenyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkynyl group, a (C1 to C4) alkoxy (C1 to C5) alkyl group, a (C1 to C4) alkoxy (C2 to C5) alkenyl group, a (C1 to C4) alkoxy (C2 to C5) alkynyl group, a (C1 to C4) alkylthîo (C1 to C5) alkyl group, a (01 to 04) alkylthio (02 to 05) alkenyl group, a (01 to 04) alkylthio (02 to 05) alkynyl group, or a group represented by any of the following Formulae (o) to (x) [Chemical Formula 4]

O

—C-Re·	-C-ORft -
ô	H 0	0
(o)	(P)	(q)
-C-Red	-C-0R_ed	—Ç^-SRed ç^_SRed
	è	ë ô _t
(r)	(s)	(t) (U)
Re· —C-tf H Ι-	R«fl —C-N	R® —Si—Ri]
Ο ΚβΤ	I R®.
(V) “ ™	(W) (_X)

here, R6a, R6b and R6c represent a C1 to 06 aikyl group which may be substituted with a halogen atom, a 02 to 06 alkenyl group which may be substituted with a halogen atom, a 02 to 06 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (06 to C10) aryl group, a substituted or unsubstituted (06 to C10) aryl (C1 to 06) alkyl group, a substituted or unsubstituted (06 to 010) aryl (02 to 06) alkenyl group, a substituted or unsubstituted (06 to C10) aryl (02 to 06) alkynyl group, a substituted or unsubstituted phenoxy (C1 to 06) alkyl group, a substituted or unsubstituted phenoxy (02 to 06) alkenyl group, a substituted or unsubstituted phenoxy (02 to 06) alkynyl group, a substituted or unsubstituted 5- to 10-membered heterocycle group, a substituted or unsubstituted 5- to 10-membered heterocycle (C1 to 06) alkyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (02 to 06) alkenyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (02 to 06) alkynyl group, a (01 to 04) alkoxy (C1 to C5) alkyl group, a (C1 to C4) alkoxy (C2 to C5) alkenyl group, a (C1 to C4) alkoxy (C2 to C5) alkynyl group, a (C1 to C4) alkylthio (C1 to C5) alkyl group, a (C1 to C4) alkylthio (C2 to C5) alkenyl group, and a (C1 to C4) alkylthio (C2 to C5) alkynyl group,

R6d represents a C1 to C6 alkyl group which may be substituted with a halogen atom, a

C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to C10) aryl group, or a substituted or unsubstituted 5- to 10-membered heterocycie,

R6e and R6f each independently represent a hydrogen atom, a C1 to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a (C1 to C4) alkoxy (C1 to C5) alkyl group, a (C1 to C4) alkylthio (C1 to C5) alkyl group, a substituted or unsubstituted (C6 to C10) aryl group, a substituted or unsubstituted (C6 to C10) aryl (C1 to C6) alkyl group, or a substituted or unsubstituted 5- to 10-membered heterocycie,

R6g and R6h each Independently represent a hydrogen atom, a C1 to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a 02 to 06 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (06 to 010) aryt group, or a substituted or unsubstituted 5- to 10-membered heterocycie, and

R6i, R6j and R6k each independently represent a hydrogen atom, a C1 to 06 aikyl group which may be substituted with a halogen atom, a 02 to 06 alkenyl group which may be substituted with a halogen atom, a 02 to 06 alkynyl group which may be substituted with a halogen atom, or a substituted or unsubstituted (06 to C10) aryl group), and

R7 represents a C1 to 06 alkyl group which may be substituted with a halogen atom, a

C1 to 06 alkenyl group which may be substituted with a halogen atom, a 02 to 06 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (06 to C10) aryl group, a substituted or unsubstituted (06 to C10) aryl (C1 to 06) alkyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkenyl group, a substituted or unsubstituted (06 to 010) aryl (02 to 06) alkynyl group, a substituted or unsubstituted phenoxy (01 to 06) alkyl group, a substituted or unsubstituted phenoxy (02 to 06) alkenyl group, a substituted or unsubstituted phenoxy (02 to 06) alkynyl group, a substituted or unsubstituted 5- to 10-membered heterocycle, a substituted or unsubstituted 5- to 10membered heterocycle (01 to 06) alkyl group, a substituted or unsubstituted 5- to 10membered heterocycle (02 to 06) alkenyl group, a substituted or unsubstituted 5- to 10membered heterocycle (02 to 06) alkynyl group, a (C1 to 04) alkoxy (C1 to 05) alkyl group, a (01 to 04) alkoxy (02 to 05) alkenyl group, a (01 to 04) alkoxy (02 to 05) alkynyl group, a (C1 to 04) alkylthio (C1 to 05) alkyl group, a (C1 to 04) alkylthio (02 to 05) alkenyl group, or a (C1 to 04) alkylthio (02 to 05) alkynyl group,

Y1 and Y2 represent an oxygen atom or a sulfur atom, and may be the same or different, and

Ry represents a 01 to 06 alkyl group which may be substituted with a halogen atom, a 02 to 06 alkenyl group which may be substituted with a halogen atom, a 02 to 06 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (06 to 010) aryl group, a substituted or unsubstituted (06 to 010) aryl (01 to 06) alkyl group, a substituted or unsubstituted (06 to 010) aryl (02 to 06) alkenyl group, a substituted or unsubstituted (06 to C10) aryl (02 to 06) alkynyl group, a substituted or unsubstituted phenoxy (01 to 06) alkyl group, a substituted or unsubstituted phenoxy (02 to 06) alkenyl group, a substituted or unsubstituted phenoxy (02 to 06) alkynyl group, a substituted or unsubstituted 5- to 10membered heterocycle, a substituted or unsubstituted 5- to 10-membered heterocycle (01 to 06) alkyl group, a substituted or unsubstituted 5- to 10membered heterocycle (02 to 06) alkenyl group, or a substituted or unsubstituted 5- to 10-membered heterocycle (02 to 06) alkynyl group,

Rz représente a C1 to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to C10) aryl group, a substituted or unsubstituted (C6 to C10) aryl (C1 to C6) alkyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkenyl group, a substituted or unsubstituted (C6 to C10) aryl (02 to 06) alkynyl group, a substituted or unsubstituted phenoxy (C1 to 06) alkyl group, a substituted or unsubstituted phenoxy (02 to 06) alkenyl group, a substituted or unsubstituted phenoxy (02 to 06) alkynyl group, a substituted or unsubstituted 5- to 10-membered heterocycle, a substituted or unsubstituted 5- to 10membered heterocycle (01 to 06) alkyl group, a substituted or unsubstituted 5- to 10membered heterocycle (02 to 06) alkenyl group, a substituted or unsubstituted 5- to 10membered heterocycle (02 to 06) alkynyl group, a (C1 to 04) alkoxy (C1 to 05) alkyl group, a (C1 to 04) alkoxy (02 to 05) alkenyl group, a (C1 to 04) alkoxy (02 to 05) alkynyl group, a (C1 to 04) alkytthio (C1 to 05) alkyl group, a (C1 to 04) alkyithio (02 to 05) alkenyl group, or a (C1 to 04) alkyithio (02 to 05) alkynyl group, and n représente 1 or 2], (2) There Is provided a pest control composition containing at least one of an amine derlvatlve represented by the following Formula (la) or acid addition saits thereof as an active ingrédient and at least one of other pest control agents:

[Chemical Formula 5] (la) [here, Ar represents a pyridyl group which may be substituted with a halogen atom, a hydroxyl group, a C1 to C6 alkyl group which may be substituted with a halogen atom, a C1 to C6 alkyloxy group which may be substituted with a halogen atom, a cyano group, or a nltro group, or a pyrlmldyl group which may be substituted with a halogen atom, a C1 to C4 alkyl group which may be substituted with a halogen atom, an alkyloxy group which may be substituted with a halogen atom, a hydroxyl group, a cyano group, or a nitro group,

Ri represents a C1 to C6 alkyl group which Is substituted with a halogen atom].

(3) There Is provided a pest control composition according to (1), wherein Ar Is a 6-chloro-3-pyrldyl group, a 6-chloro-5-fiuoro-3-pyrldyl group, a 6-fiuoro3-pyridyl group, a 6-bromo-3-pyridyl group, or a 2-chioro-5-pyrimidyl group.

(4) There is provided a pest control composition according to (1) or (3), wherein in Formula (l), A Is the following Formula (A-1):

[Chemical Formula 6] (A-1) and Y Is a hydrogen atom, a halogen atom, or a cyano group.

(5) There is provided a pest control composition according to (1),(3) to (4), wherein R in Formula (l) Is a group with Formula (c).

[Chemical Formula 7] —c-r₃

Il ⁰

S (0 (6) There is provided a pest control composition according to (1),(3) to (4), wherein R in Formula (I) Is a group with Formula (a).

[Chemical Formula 8] —C-Rî

Il ¹ o

(a) (7) There is provided a pest control composition according to (1),(3) to (4), wherein R in Formula (I) is a group with Formula (d) [[Chemical Formula 9] —c-r₅

Il ⁰

N i

R₄ (d) and R4 is a C1 to C18 alkyl group which may be substituted, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to C10) aryl group, a substituted or unsubstituted (C6 to C10) aryl (C1 to C6) alkyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkenyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkynyl group, a substituted or unsubstituted phenoxy (C1 to C6) alkyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkenyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkynyl group, a substituted or unsubstituted 5- to 10-membered heterocycle, a substituted or unsubstituted 5- to 10membered heterocycle (C1 to C6) alkyl group, a substituted or unsubstituted 5 to 10-membered heterocycle (C2 to C6) alkenyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkynyl group, a (C1 to C4) alkoxy (C1 to C5) alkyl group, a (C1 to C4) alkoxy (C2 to C5) alkenyl group, a (C1 to C4) alkoxy (C2 to C5) alkynyl group, a (C1 to C4) alkylthio (C1 to C5) alkyl group, a (C1 to C4) alkylthio (C2 to C5) alkenyl group, or a (C1 to C4) alkylthio (C2 to C5) alkynyl group, and

R5 ls a C1 to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, and R5 ls a C1 to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, or a C2 to C6 alkynyl group which may be substituted with a halogen atom.

(Θ) There is provided a pest control composition according to (1), wherein the Iminopyrldlne derlvative ls N-[1-((6-chloropyridln-3-yl)methyl)pyridin-2(1H)ylldene]-2,2,2-trifluoroacetamide or N-[1-((6-chloropyridin-3-yl)methyl)pyridln2(1H)-ylidene]-2,2,2-trifiuoroethanethloamlde, or N-[1-((6-chloropyrldin-3yl)methyl)pyrldin-2(1H)-ylidene]-2,2,2-trlfluoro-N'-lsopropylacetimldamlde.

(9) There ls provided a method for protecting useful plants or animais from pests, including: treating pests, useful plants, seeds of useful plants, soil, cultivation carriers or animais as a target with an effective amount of the pest control composition.

(10) There ls provided a combination including the Iminopyridine dérivative represented by Formula (I) and at least one of other pest control agents.

(11) There is provided a use of the pest control composition for protecting useful plants or animais from pests.

[Advantageous Effects of Invention]

It ls possible to effectlvely perform pest control against cabbage moths, Spodoptera lltura, aphlds, planthoppers, leafhoppers, thrips and other numerous pests by using novel imlnopyridine dérivative of the présent invention.

[Description of Embodiments]

A novei iminopyridine dérivative represented by Formula (I) may be prepared by the foliowing method.

[Chemical Formula 10]

(i-1) may be obtained by reacting a compound represented by the foliowing Formula (II· 1) with a compound represented byArCH2X [the définition of Ar, A, Y and R1 has the same meaning as the définition described above, and X represents a halogen atom or OTs, OMs and the like] in the presence or absence of a base.

[Chemical Formula 11]

N .R, (ll-D

When the reaction Is performed in the presence of a base, it is possible to use, for example, an alkali métal hydride such as sodium hydride, a carbonate such as potassium carbonate or sodium carbonate, an alkali métal hydroxide such as potassium hydroxide, and sodium hydroxide, tertiary amines such as triethylamine and 1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted or substituent-containing pyridines, such as pyridine and 4dimethylaminopyridine, as the base.

The reaction may be performed without a solvent or using a solvent which does not affect the reaction, and when a solvent is used, It Is possible to use solvents such as, for example, amides such as Ν,Ν-dimethylformamide and Ν,Ν-dimethylacetamide, nitriles such as acetonîtrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, éthanol, propanol and Isopropyl alcohol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, and halogen hydrocarbons such as dichloromethane, chlorofonm, chlorobenzene and dichlorobenzene, either alone or ln combination of two or more thereof, but N.N-dimethylformamlde and the like are preferably used.

The réaction may be performed usually at 0°C to 200°C, and It is preferred that reagents are added at 20°C to 40°C and the reaction Is performed at 60°C to 80°C.

The compound represented by Formula (11-1) may be obtained by reacting a compound represented by R1-C(=O)X, R1-C(=O)OC(=O)R1₁ R1C(=O)OR' [X represents a halogen atom or OTs, OMs and the like, R’ represents a C1 to C6 alkyl group, and the définition of R1, A and Y has the same meanlng as the définition described above] and the like with a compound represented by the following Formula (III) ln the presence or absence of a base, [Chemical Formula 12] ί A -*-*

N, y

T

NH₃ (III)

When the réaction is performed in the presence of a base, it is possible to use, for example, an alkali métal hydride such as sodium hydrlde, a carbonate such as potassium carbonate or sodium carbonate, an alkali métal hydroxide such as potassium hydroxide and sodium hydroxide, tertiary amines such as triethylamine and 1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted or substituent-containing pyridines, such as pyridine and 4dimethylaminopyridine as the base.

The reaction may be performed without a solvent or using a solvent which does not affect the reaction. When a solvent Is used, It Is possible to use solvents such as, for example, amides such as Ν,Ν-dimethylformamide and N.N-dimethylacetamide, nitriles such as acetonitriie, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, éthanol and propanol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, halogen hydrocarbons such as dlchloromethane, chloroform, chlorobenzene and dichlorobenzene, and water, either alone or in combination of two or more thereof, but toluene, Ν,Ν-dimethylformamide, acetonitrile, ethers, dlchloromethane, chloroform and the like are preferably used.

The reaction may be performed usually at -80°C to 100°C, and Is performed preferably in a range from 20°C to 50°C. The compound represented by Formula (11-1) may be obtained by reacting the compound represented by Formula (III) with a carboxylic acid represented by R1-COOH [the définition of R1 has the same meaning as the définition described above] using a déhydration condensation agent In the presence or absence of a base, or may be obtained by performing the réaction using phosphorus pentaoxlde, sulfuric acid, polyphosphoric acid, thionyl chloride, phosphorus oxychloride and oxalyl dichloride ln the absence of a base.

It Is possible to use a carbodiimide-based compound such as dicyclohexylcarbodiimide and 1-ethyl-3-(3-[dimethylaminopropy1])carbodiimide hydrochloride as the déhydration condensation agent.

When the reaction Is performed in the presence of a base, it Is possible to use, for example, a carbonate such as potassium carbonate or sodium carbonate, tertiary amines such as triethylamlne and 1,8-diazablcyclo[4.3.0]non-5-ene, and unsubstituted or substituentcontaining pyridines, such as pyridine and 4-dimethylaminopyridine, as the base.

The reaction is preferably performed by using a solvent, and it is possible to use solvents such as, for example, amides such as N,N-dimethy1formamide and N,Ndimethylacetamide, nitrites such as acetonitrile, sulfoxldes such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, and halogen hydrocarbons such as dlchloromethane, chloroform, chlorobenzene and dichlorobenzene, either alone or In combination of two or more thereof, but dichloromethane, chloroform and the like are preferably used.

The reaction may be performed usually at -80°C to 100°C, and is performed preferably in a range from 20°C to 50°C. The compound représenter! by Formula (1-1 ) may be obtained by reacting a compound représenter! by R1-C(=O)X, R1-C(=O)OC(=O)R1, R1C(=O)OR’ [X represents a halogen atom or OTs, OMs and the like, R' represents a C1 to C6 alkyl group, and the définition of Ar, A, Y and R1 has the same meaning as the définition described above] and the like with a compound représenter! by the following Formula (IV) In the presence or absence of a base.

[Chemical Formula 13]

(IV)

When the reaction is performed In the presence of a base, it is possible to use, for example, an alkall métal hydride such as sodium hydride, a carbonate such as potassium carbonate or sodium carbonate, an alkali métal hydroxide such as potassium hydroxide and sodium hydroxide, tertiary amines such as triethylamlne and 1,8-diazabicyclo[4,3.0]non-5-ene, and unsubstituted or substituent-containing pyridines, such as pyridine and 4dimethylaminopyridine as the base.

The reaction may be performed without a solvent or using a solvent which does not affect the reaction. When a solvent is used, it is possible to use solvents such as, for exampie, amides such as Ν,Ν-dimethylformamlde and Ν,Ν-dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethy! ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, éthanol and propanol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, and water, either alone or in combination of two or more thereof, but toluene,

Ν,Ν-dimethylformamide, acetonitrile, ethers, dichloromethane, chloroform and the like are preferably used.

The reaction may be performed usually at -80°C to 100°C, and Is performed preferably In a range from 20°C to 50°C. The compound represented by Formula (1-1 ) may be obtained by reacting the above-described compound represented by Formula (IV) with a carboxylic acid represented by R1-COOH [the définition of R1 has the same meaning as the définition described above] using a déhydration condensation agent in the presence or absence of a base, or may be obtained by performlng the reaction using phosphorus pentaoxlde, sulfuric acid, polyphosphoric acid, thionyl chloride, phosphorus oxychloride and oxalyl dichloride in the absence of a base.

It is possible to use a carbodiimide-based compound such as dicyclohexylcarbodiimide and 1-ethyl-3-(3-dÎmethylaminopropyl)carbodiimlde hydrochloride as the déhydration condensation agent.

When the reaction is performed in the presence of a base, it is possible to use, for example, a carbonate such as potassium carbonate or sodium carbonate, tertiary amines such as triethylamine and 1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstîtuted or substituentcontalning pyrldines, such as pyridine and 4-dimethylaminopyridine, as the base.

The reaction Is preferably performed by using a solvent, and it is possible to use solvents such as, for example, amides such as Ν,Ν-dimethylformamide and N,Ndimethylacetamîde, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, ketones such as acetone and methyi ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, either alone or in combination of two or more thereof, but dichloromethane, chloroform and the like are preferably used.

The reaction may be performed usualiy at -80°C to 100°C, end is performed preferably in e range from 20°C to 50°C. The compound represented by Formula (IV) may be obtained by reacting the ebove-described compound represented by Formula (III) with a compound represented by ArCH2X [the définition of Ar end X has the same meaning as the définition described ebove] in the presence or ebsence of e base.

When the reaction is performed in the presence of e base, it is possible to use, for example, en elkali métal hydride such es sodium hydride, e carbonate such es potassium carbonate or sodium carbonate, en elkali métal hydroxide such es potassium hydroxide and sodium hydroxide, tertiary emines such es triethylamine end 1,8-diazabicyclo[4.3.0]non-5-ene, end unsubstituted or substituent-containing pyridines, such es pyridine end 4dimethylaminopyridine, es the base.

The reaction may be performed without e solvent or using e solvent which does not effect the reaction. When e solvent is used, it is possible to use solvents such es, for example, emides such es Ν,Ν-dimethylformamide end N.N-dimethylacetamide, nitriles such es ecetonitrile, sulfoxides such es dimethyl sulfoxide, ethers such es diethyl ether end tetrahydrofuran, esters such es ethyl ecetate end butyl ecetate, eromatic hydrocarbons such es benzene, xylene and toluene, alcohols such as methanol, éthanol end propanol, ketones such as ecetone end methyl ethyl ketone, aliphatic hydrocarbons such es hexane, heptane end octane, halogen hydrocarbons such es dichloromethane, chloroform, chlorobenzene end dichlorobenzene, end water, either elone or in combination of two or more thereof, but N,Ndimethylformamide, acetonitrile, ethers, dichloromethane, chloroform end the like are preferably used.

The reaction may be performed usualiy et -80°C to 100°C, end ls performed preferably In e range from 20°C to 80°C.

When Formula (1-1) is synthesized via Formula (11-1) from the compound represented by Formula (III), or when Formula (1-1) ls synthesized via Formula (IV) from the compound represented by Formula (III), the reaction may be continuously performed without taking out

Formula (11-1) or Formula (IV), or the réactions from Formula (III) to Formula (1-1) may be slmultaneously performed in the same vessei.

[Chemical Formula 14]

n_or₂ (I - 2 )

The compound represented by Formula (I-2) may be obtained by reacting a compound represented by the following Formula (l-2a) with a compound represented by ArCH2X [the définition of Ar, A, Y and R2 has the same meaning as the définition described above, and X représents a halogen atom or OTs, OMs and the like] In the presence or absence of a base. [Chemical Formula 15]

(I — 2a)

When the reaction Is performed ln the presence of a base, It is possible to use, for example, an alkali métal hydride such as sodium hydride, a carbonate such as potassium carbonate or sodium carbonate, an alkaii métal hydroxide such as potassium hydroxide and sodium hydroxide, tertiary amines such as triethylamine and 1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted or substituent-containing pyridines, such as pyridine and 4dimethylaminopyridine, as the base.

The reaction may be performed without a solvent or using a solvent which does not affect the reaction, and when a solvent Is used, It is possible to use solvents such as, for example, amides such as N,N-dimethylformamlde and Ν,Ν-dimethylacetamlde, nltriles such as acetonitrile, sulfoxldes such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, éthanol, propanol and Isopropyl alcohol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, and halogen hydrocarbons such as dîchloromethane, chloroform, chlorobenzene and dichlorobenzene, either alone or in combination of two or more thereof, but

Ν,Ν-dimethylformamide and the like are preferably used.

The reaction may be performed usually at 0°C to 200°C, and It is preferred that reagents are added at 20°C to 40°C and the reaction Is performed at 60°C to 80°C.

The compound represented by Formula (l-2a) may be obtained by reacting the abovedescribed compound represented by Formula (III) with a compound represented by R2OC(=O)X (the définition of R2 and X has the same meantng as the définition described above] or represented by the following Formula (l-2b) in the presence or absence of a base. [Chemical Formula 16]

(I — 2b)

When the reaction is performed in the presence of a base, it is possible to use, for example, an alkali métal hydride such as sodium hydride, a carbonate such as potassium carbonate or sodium carbonate, an alkali métal hydroxide such as potassium hydroxide and sodium hydroxide, tertiary amines such as triethylamine and 1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted or substituent-containing pyridines, such as pyridine and 4dimethylaminopyridine as the base.

The reaction may be performed without a solvent or using a solvent which does not affect the reaction, and when a solvent Is used, it is possible to use solvents such as, for example, amides such as Ν,Ν-dimethylformamide and N,N-dimethylacetamide, nitrites such as acetonitrile, sulfoxldes such as dimethyl sulfoxide, ethers such as diethyl ether, and tetrahydrofuran, esters such as ethyi acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, éthanol, propanol and isopropyl alcohol, ketones such as acetone and methyl ethyi ketone, aliphatic hydrocarbons such as hexane, heptane and octane, and halogen hydrocarbons such as dîchloromethane, chloroform, chlorobenzene and dichlorobenzene, either alone or in combination of two or more thereof, but acetonitrile, dichloromethane or the like is preferably used.

The reaction may be performed usually at 0°C to 200°C, and Is performed preferably at 20°C to 80°C.

The compound represented by Formula (1-2) may be obtained by reacting the abovedescribed compound represented by Formula (IV) with a compound represented by R2OC(=O)X (the définition of R2 and X has the same meaning as the définition described abovej or represented by the above-described Formula (l-2b) in the presence or absence of a base. When the réaction Is performed in the presence of a base, It is possible to use, for example, an alkali métal hydride such as sodium hydride, a carbonate such as potassium carbonate or sodium carbonate, an alkali métal hydroxide such as potassium hydroxide and sodium hydroxide, tertlary amines such as triethylamine and 1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted or substituent-containing pyridines, such as pyridine and 4dimethylaminopyridine as the base.

The reaction may be performed without a solvent or using a solvent which does not affect the reaction, and when a solvent is used, It Is possible to use solvents such as, for example, amldes such as Ν,Ν-dimethylformamide and Ν,Ν-dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, éthanol, propanoi and isopropyl alcohol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dlchlorobenzene, either alone or in combination of two or more thereof, but acetonitrile, dichloromethane or the like Is preferably used.

The reaction may be performed usually at 0°C to 200°C, and Is performed preferably at 20°C to 80^eC.

[Chemical Formula 17]

Τ'

V’ ¢1-3)³

The compound represented by Formula (1-3) may be synthesized by acting a sulfurizing reagent on a compound (the définition of Ar, A, Y and R3 has the same meaning as the définition described above) represented by the following Formula (ll-3a), which may be synthesized in the same manner as described in Formula (i-1), in the presence or absence of a base.

[Chemical Formula 18]

Y¹

CI I — 3a)

When the reaction is performed in the presence of a base, It is possible to use, for exampie, an alkaii métal hydride such as sodium hydride, a carbonate such as potassium carbonate or sodium carbonate, an alkaii métal hydroxide such as potassium hydroxide and sodium hydroxide, tertiary amines such as triethylamine and 1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted or substituent-containing pyridines, such as pyridine and 4dimethylaminopyridine as the base, but potassium carbonate, sodium carbonate or the like is preferably used.

As the sulfurizing reagent, phosphores pentasulfide, Lawessorïs reagent, hydrogen sulfide and the like may be used.

The reaction may be performed without a solvent or using a solvent which does not affect the reaction, and when a solvent Is used, It 1s possible to use solvents such as, for example, amides such as N.N-dimethylformamide and N.N-dimethylacetamide, nitrites such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatîc hydrocarbons such as benzene, xylene and toiuene, alcohols such as methanol, éthanol and propanol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, either atone or In combination of two or more thereof, but toluene, tetrahydrofuran or the like Is preferably used.

The reaction may be performed usually at -80°C to 100°C, and Is performed preferably In a range from 20°C to 80°C. The compound represented by Formula (I-3) may be obtained by reacting a compound represented by the following Formula (ll-3b) with a compound represented by ArCH2X [the définition of Ar, A, Y and R3 has the same meaning as the définition described above, and X represents a halogen atom or OTs, OMs and the iike] In the presence or absence of a base.

[Chemical Formula 19]

(II-3 b)

When the reaction Is performed In the presence of a base, it Is possible to use, for exampie, an aikaii métal hydride such as sodium hydride, a carbonate such as potassium carbonate or sodium carbonate, an aikaii métal hydroxide such as potassium hydroxide and sodium hydroxide, tertiary amines such as triethylamlne and 1,8-diazablcyc!o[4.3.0]non-5-ene, and unsubstituted or substituent-containing pyridines, such as pyridine and 4~ dimethylaminopyridine as the base.

The reaction may be performed without a solvent or using a solvent which does not affect the reaction, and when a solvent Is used, It is possible to use solvents such as, for example, amides such as Ν,Ν-dïmethylformamide and N.N-dimethylacetamide, nitriies such as acetonitrile, sulfoxldes such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, éthanol, propanol and isopropyl alcohoi, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, either alone or in combination of two or more thereof, but Ν,Ν-dimethylformamide and the like are preferably used.

The compound represented by Formula (ll-3b) may be synthesized by acting a sulfurizing reagent on a compound (the définition of A, Y and R3 has the same meaning as the définition described above) represented by Formula (ll-3c), which may be synthesized in the same manner as described In Formula (11-1), in the presence or absence of a base.

[Chemical Formula 20]

(II — 3 c)

When the reaction Is performed in the presence of a base, it is possible to use, for example, an alkali métal hydride such as sodium hydride, a carbonate such as potassium carbonate or sodium carbonate, an alkali métal hydroxide such as potassium hydroxide and sodium hydroxide, tertiary amines such as triethylamine and 1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted or substituent-containing pyridines, such as pyridine and 4dimethylaminopyridlne as the base, but potassium carbonate, sodium carbonate or the like is preferably used.

As the sulfurizing reagent, phosphores pentasulfide, Lawesson’s reagent, hydrogen sulfide and the like may be used. The reaction may be performed without a solvent or using a solvent which does not affect the reaction, and when a solvent Is used, It Is possible to use solvents such as, for example, amides such as Ν,Ν-dimethylformamide and N.Ndimethylacetamide, nitriles such as acetonîtrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, éthanol and propanol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichiorobenzene, either alone or ln combination of two or more thereof, but toluene, tetrahydrofuran and the like are preferably used.

The reaction may be performed usually at -80°C to 100°C, and Is performed preferably ln a range from 20°C to 80°C.

[Chemical Formula 21]

(I-4)

The compound represented by Formula (I-4) may be obtained by reacting a compound represented by the following Formula (ll-4a), which may be synthesized in the same manner as described ln Formula (I-3) with a compound represented by R4-NH2 (the définition of Ar, A, Y, R4 and R5 has the same meaning as the définition described above).

[Chemical Formula 22] ·* \ t A -j-Y ^Αγ'^^ν'ίι*'

T (II-4 a)

The reaction may be performed without a solvent or using a solvent which does not affect the reaction, and when a solvent Is used, it Is possible to use solvents such as, for example, amides such as Ν,Ν-dimethylformamide and Ν,Ν-dimethylacetamÎde, nitriles such as acetonitrile, sulfoxldes such as dimethyl sulfoxlde, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, éthanol and propanol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, either alone or in combination of two or more thereof, but alcohols such as methanol and éthanol are preferably used.

The reaction, If performed in the presence of sifver carbonate, copper carbonate and the like, progresses quickly, but may proceed without the compound.

The reaction may be performed usually at -80°C to 100°C, and Is performed preferably In a range from 20°C to 80°C.

The compound represented by Formula (I-4) may be obtained by reacting a compound represented by the following Formula (l-4b) or a sait thereof with R4-X, R4-O-R4 and R4-OR' (the définition of R4, R’, Ar, A, Y and R5 has the same meaning as the définition described above, and X represents a halogen atom) in the presence or absence of a base.

[Chemical Formula 23]

(I — 4 b)

When the reaction Is performed in the presence of a base, it is possible to use, for example, an alkali métal hydride such as sodium hydride, a carbonate such as potassium carbonate or sodium carbonate, an alkali métal hydroxide such as potassium hydroxide and sodium hydroxide, tertiary amines such as triethylamine and 1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted or substituent-containïng pyridines, such as pyridine and 4dimethylaminopyridine as the base.

The reaction may be performed without a solvent or using a solvent which does not affect the reaction. When a solvent is used, It is possible to use solvents such as, for example, amldes such as Ν,Ν-dimethylformamide and Ν,Ν-dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyt ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, éthanol and propanol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, and water either alone or In combination of two or more thereof, but toluene, dimethyiformamide, acetonitrile, ethers, dichloromethane, chloroform and the like are preferably used.

The réaction may be performed usually at -80°C to 100°C, and is performed preferably in a range from 20°C to 50°C. The compound represented by Formula (l-4b) may be obtained by reacting a compound represented by Formula (ll-4a) with ammonia or an alcohol solution thereof, ammonium chloride and the like.

The reaction may be performed without a solvent or using a solvent which does not affect the reaction. When a solvent is used, it is possible to use solvents such as, for example, amides such as Ν,Ν-dimethylformamide and N,N-dimethylacetamide, nitriles such as acetonitrile, suifoxides such as dimethyl sulfoxide, ethers such as diethyî ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, éthanol and propanol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, and water, either alone or In combination of two or more thereof, but alcohols such as methanol and éthanol are preferably used.

The reaction may be performed usually at -80°C to 100°C, and is performed preferably In a range from 20°C to 50°C.

[Chemical Formula 24]

“OR# (I-5 )

The compound represented by Formula (I-5) may be obtained by reacting a compound represented by the foliowing Formula (I l-5b) with R6-X (the définition of AR, A, Y, R6 and R7 has the same meaning as the définition described above, and X represents a halogen atom), R6-O-R6 or R6-OR* (the définition of R* has the same meaning as the définition described above) In the presence or absence of a base.

[Chemical Formula 25] (11-5 b)

When the réaction is performed In the presence of a base, it is possible to use, for example, an alkali métal hydride such as sodium hydride, a carbonate such as potassium carbonate or sodium carbonate, an alkali métal hydroxide such as potassium hydroxide and sodium hydroxide, tertiary amines such as triethylamine and 1,8-diazablcyclo[4.3.0]non-5-ene, and unsubstituted or substituent-containlng pyridines, such as pyridine and 4dimethylaminopyridine as the base.

The reaction may be performed without a solvent or using a solvent which does not affect the reaction. When a solvent is used, It Is possible to use solvents such as, for example, amides such as Ν,Ν-dimethylformamlde and Ν,Ν-dimethylacetamide, nltriles such as acetonîtrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, éthanol and propanol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, and water, either alone or ln combination of two or more thereof, but toluene, Ν,Ν-dimethylformamlde, acetonitrile, ethers, dichloromethane and chloroform are preferably used.

The reaction may be performed usually at -80°C to 100°C, and is performed preferably

In a range from 20°C to 50°C.

When R6 représente -C(=O)R6a (R6a has the same meanlng as described above), the compound represented by Formula (1-5) may be obtained by reacting the compound represented by Formula (ll-5b) with a carboxylic acid represented by R6a-C(=O)OH (the définition of R6a has the same meaning as the définition described above) using a déhydration condensation agent In the presence or absence of a base, or may be obtained by performlng the réaction using phosphorus pentaoxide, sulfuric acid, polyphosphoric acid, thionyl chioride, phosphorus oxychloride and oxalyl di ch Ion de In the absence of a base.

It Is possible to use a carbodiimide-based compound such as dicyclohexylcarbodilmide, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and the like as the déhydration condensation agent.

When the reaction is performed in the presence of a base, it Is possible to use, for example, a carbonate such as potassium carbonate or sodium carbonate, tertiary amines such as triethylamine and 1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted or substituentcontaining pyridines, such as pyridine and 4-dimethylaminopyridine as the base.

The reaction Is preferably performed by using a solvent, and it Is possible to use, for example, amides such as N.N-dimethytformamide and Ν,Ν-dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyi acetate and butyl acetate, aromatic hydrocarbons such as benzene, xytene and toluene, ketones such as acetone and methyl ethyi ketone, aliphatic hydrocarbons such as hexane, heptane and octane, and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, either alone or In combination of two or more thereof, but dichloromethane, chloroform and the like are preferably used.

When R6 represents CONR6eR6f (the définition of R6e and R6f has the same meaning as the définition described above, and R6e or R6f represents a hydrogen atom) or CSNR6gR6h (the définition of R6g and R6h has the same meaning as the définition described above, and R6g or R6h represents a hydrogen atom), the compound of Formula (1-5) may be obtained by reacting the Formula (ll-5b) with a compound represented by RN=C=O (R represents a C1 to C6 alkyl group which may be substituted with a halogen atom, a C2 to 06 alkenyl group which may be substituted with a halogen atom, a 02 to 06 alkynyl group which may be substituted with a halogen atom, a (C1 to 04) alkoxy (C1 to 05) alkyl group, a (C1 to 04) alkylthio (C1 to 05) alkyl group, a substituted or unsubstituted (06 to C10) aryl group, and a substituted or unsubstituted 5- to 10-membered heterocycle) in the presence or absence of a base. When the reaction Is performed In the presence of a base, it is possible to use, for example, an alkali métal hydride such as sodium hydride, a carbonate such as potassium carbonate or sodium carbonate, an alkali métal hydroxide such as potassium hydroxlde and sodium hydroxide, tertiary amines such as triethylamine and 1,8-diazablcyclo[4.3.0]non-5-ene, and unsubstituted or substituent-containing pyridines, such as pyridine and 4dimethylaminopyridine as the base. The reaction Is preferably performed by using a solvent, and it is possible to use, for example, amides such as Ν,Ν-dimethylformamide and N,Ndimethylacetamide, nitriles such as acetonitrile, sulfoxldes such as dimethyl sulfoxlde, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, either alone or in combination of two or more thereof, but nitriles such as acetonitrile are preferably used.

When R6 represents CONR6eR6f (the définition of R6e and R6f has the same meaning as the définition described above), the compound of Formula (I-5) may be obtained by reacting the above-described compound represented by Formula (ll-5b) with a compound represented by the following Formula (ll-5c) ln the presence or absence of a base.

[Chemical Formula 26] (11 — 5 c )

When the reaction Is performed ln the presence of a base, it Is possible to use, for example, an aikali métal hydride such as sodium hydride, a carbonate such as potassium carbonate or sodium carbonate, an aikali métal hydroxide such as potassium hydroxide and sodium hydroxide, tertiary amines such as triethylamine and 1,8-diazabicycio[4.3.0]non-5-ene, and unsubstituted or substituent-containing pyridines, such as pyridine and 4dimethylamlnopyridine as the base.

The reaction is preferably performed by using a solvent, and It is possible to use, for example, amides such as N,N-dimethylformamide and Ν,Ν-dimethylacetamide, nitrites such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichiorobenzene, either alone or In combination of two or more thereof, but nitrites such as acetonitrile are preferably used.

The compound represented by Formula (ll-5b) may be obtained by reacting the compound (the définition of Ar, A, Y and R7 has the same meaning as the définition described above) represented by Formula (ll-5a), which may be synthesized In the same manner as described in Formula (I-3) with hydroxylamïne or a sait thereof in the presence or absence of a base.

[Chemical Formula 27]

s

Cl I — 5a)

When the reaction is performed in the presence of a base, It Is possible to use, for example, an alkali métal hydride such as sodium hydride, a carbonate such as potassium carbonate or sodium carbonate, an alkali métal hydroxide such as potassium hydroxide and sodium hydroxide, tertiary amines such as triethylamine and 1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstîtuted or substituent-contalning pyridines, such as pyridine and 4dimethylaminopyridine as the base.

The reaction may be performed without a solvent or using a solvent which does not affect the reaction. When a solvent is used, it is possible to use solvents such as, for example, amldes such as Ν,Ν-dimethylformamide and Ν,Ν-dimethylacetamide, nitriles such as acetonitrile, suifoxides such as dimethyl sulfoxlde, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, éthanol and propanol, ketones such as acetone and methyi ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, and water, either alone or in combination of two or more thereof, but toluene, Ν,Ν-dimethylformamide, acetonitrile, ethers, dichloromethane, chloroform and the like are preferably used.

The compound represented by Formula (i-5) may also be obtained by reacting the compound represented by Formula (ll-5a) with a compound represented by R6-ONH2 or a sait thereof in the presence or absence of a base.

When the reaction Is performed In the presence of a base, It is possible to use, for example, an alkali métal hydride such as sodium hydride, a carbonate such as potassium carbonate or sodium carbonate, an alkali métal hydroxide such as potassium hydroxide and sodium hydroxide, tertiary amines such as triethylamine and 1,8-diazabicycio[4.3.0]non-5-ene, and unsubstituted orsubstituent-containing pyridines, such as pyridine and 4dimethylamlnopyridine as the base.

The reaction may be performed without a solvent or using a solvent which does not affect the reaction. When a solvent ls used, it is possible to use solvents such as, for example, amides such as Ν,Ν-dimethylformamide and Ν,Ν-dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, éthanol and propanol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, and water, either alone or In combination of two or more thereof, but alcohols such as methanol and éthanol are preferably used.

The reaction may be performed usualiy at -80°C to 100°C, and is performed preferably in a range from 20°C to 80°C.

The reaction, If performed in the presence of silver carbonate, copper carbonate and the like, progresses qulckly, but may proceed without the compound.

[Chemical Formula 28]

d-6)

The compound represented by Formula (1-6) [the définition of Ar, A, Y, Y1, Y2,and Ry has the same meaning as the définition described above] may be obtained by reacting according to Phosphores, sulfur, and silicon and the related éléments (2006) 181,2337-2344.

[Chemical Formula 29]

d-7)

The compound represented by Formula (1-7) [the définition of Ar, A, Y, Ry and n has the same meanlng as the définition described above] may be obtained by reacting a compound represented by the following Formula (ll-7a) with a compound represented by ArCH2X [the définition of Ar has the same meaning as the définition described above, and X représente a halogen atom or OTs, OMs and the like] ln the presence or absence of a base.

[Chemical Formula 30]

N_Xg>Rz

(ll-7a)

When the reaction is performed ln the presence of a base, it is possible to use, for example, an alkali métal hydride such as sodium hydride and the like, a carbonate such as potassium carbonate or sodium carbonate and the like, an alkali métal hydroxide such as potassium hydroxide, sodium hydroxide and the iike, tertiary amines such as triethylamine, 1,8-diazabicyclo[4.3.0]non-5-ene and the like, and unsubstituted or substituent-contalning pyridines, such as pyridine, 4-dimethylaminopyridine and the like, as the base.

The reaction may be performed without a solvent or using a solvent which does not affect the reaction, and when the solvent Is used, It Is possible to use solvents such as, for example, amldes such as Ν,Ν-dimethylformamide and N.N-dimethylacetamide, nitrites such as acetonitrile, sulfoxldes such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatîc hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, éthanol, propanol and Isopropyl alcohol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dlchlorobenzene, either alone or In combination of two or more thereof, but Ν,Ν-dimethylformamide and the like are preferably used.

The reaction may be performed usually at from 0°C to 200°C, and it is preferred that reagents are added at from 20°C to 40°C and the reaction Is performed at from 60°C to 80°C.

The compound represented by Formula (ll-7a) may be obtained by reacting a compound represented by (ll-7b) [X represents a halogen atom, and the définition of Rz and n has the same meanlng as the définition described above] with a compound represented by in the following Formula (III) in the presence or absence of a base.

[Chemical Formula 31]

X._e.Rz |δ|„ (ll-7b)

When the reaction is performed in the presence of a base, it is possible to use, for example, an alkaii métal hydride such as sodium hydride and the like, a carbonate such as potassium carbonate or sodium carbonate and the like, an alkaii métal hydroxide such as potassium hydroxide, sodium hydroxide and the like, tertiary amines such as triethylamine, 1,8diazablcyclo[4.3.O]non-5-ene and the like, and unsubstituted or substituent-containing pyridines, such as pyridine, 4-dimethylamlnopyrldine and the like, as the base.

The reaction may be performed without a solvent or using a solvent which does not affect the réaction, and when the solvent is used, It is possible to use solvents such as, for example, amides such as Ν,Ν-dimethyiformamlde and Ν,Ν-dimethylacetamide, nitriles such as acetonitrile, sulfoxldes such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatîc hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, éthanol, propanol and Isopropyl alcohol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, either alone or In combination of two or more thereof, but N.N-dimethylformamide and the like are preferably used.

The compound represented by Formula (1-7) may be obtained by reacting a compound represented by (ll-7b) [X represents a halogen atom, and the définition of Rz has the same meaning as the définition described above] with a compound represented by in the following Formula (IV) In the presence or absence of a base.

When the reaction Is performed In the presence of a base, it is possible to use, for example, an alkall meta! hydride such as sodium hydride and the iike, a carbonate such as potassium carbonate or sodium carbonate and the like, an alkall métal hydroxide such as potassium hydroxide, sodium hydroxide and the like, tertiary amines such as triethylamine, 1,8diazablcyclo[4.3.0]non-5-ene and the like, and unsubstituted or substituent-contalnlng pyridines, such as pyridine, 4-dimethylaminopyridine and the like, as the base.

The reaction may be performed without a solvent or using a solvent which does not affect the reaction, and when the solvent Is used, it is possible to use solvents such as, for example, amides such as N.N-dimethylformamide and N,N-dimethylacetamide, nltriles such as acetonitrile, sulfoxides such as dimethyl sulfoxlde, ethers such as diethyi ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, éthanol, propanol and isopropyl alcohol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, either alone or ln combination of two or more thereof, but N,Ndlmethylformamlde and the like are preferably used.

The reaction may be performed usually at from 0°C to 200°C, and It 1s preferred that the reaction Is performed at from 0°C to 80°C.

Examples of a substituent that may be substituted of a phenyl group which may be substituted* and a 5- to 6-membered heterocycle which may be substituted, which are represented by Ar, Include a halogen atom, a C1 to C4 alkyl group which may be substituted with a halogen atom, a C1 to C4 alkyloxy group which may be substituted with a halogen atom, a hydroxy) group, a cyano group, a nitro group and the like, preferably a halogen atom, a trifluoromethyf group and a cyano group, and particulariy preferably a halogen atom.

Spécifie examples of the a phenyl group which may be substituted* represented by Ar of a nitrogen-containing heterocyclic dérivative compound having a 2-imino group represented by Formula (I) Include a phenyl group and a 3-cyano phenyl group.

A 5- to 6-membered heterocycle which may be substituted, represented by Ar of a nitrogen-containing heterocyclic dérivative compound having a 2-lmino group represented by Formula (I) represents an aromatic 5- to 6-membered heterocycle including one or two of a heteroatom such as an oxygen atom, a sulfur atom or a nitrogen atom, spécifie examples thereof Include a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, a thiazole ring, an oxazole ring and the like, and préférable aspects thereof Include a 6-chloro-3-pyridyl group, a 6-chloro-5-fluoro-3-pyridyl group, a 6-bromo-3-pyridyl group, a 6-fluoro-3-pyridyl group, a 6-trifluoromethyl-3-pyridyl group, a 6-chloro-3-pyridazinyl group, a 5-chloro-2pyrazinyl group, a 2-chloro-5-pyrimidinyl group, a 2-chloro-5-thlazolyl group, a 2-chloro-4pyridyl group, and more preferably a 6-chloro-3-pyridyl group, a 6-fluoro-3-pyridyl group, a 6chloro-5-fluoro-3-pyridyl group, a 6-bromo-3-pyridyl group and a 2-chloro-5-pyrimidinyl group.

Spécifie examples of a 4- to 10-membered heterocycloalkyl group represented by Ar of a nitrogen-containing hetero ring dérivative having a 2-imino group represented by Formula (I) Include a 2-tetrahydrofuranyl group, a 3-tetrahydrofuranyl group and the like and preferably a

3-tetrahydrofuranyl group. A heterocycle having a 5- to 10-membered unsaturated bond including one or more nitrogen atoms, which A of a nitrogen-contalnlng heterocyclic dérivative having a 2-lmino group represented by Formula (i) represents, means that [Chemical Formula 32]

In Formula (I) represents any one ring represented by each of the following Formulae A1 to A-40. ln each formula, the end of a double bond is the substitution position of a nitrogen atom.

[Chemical Formula 33]

[Chemical Formula 34]

[Chemical Formula 35]

[Chemical Formula 37]

The ring is preferably the ring of FormulaeA-1, A-13, A-14, A-15, A-16, A-23, A-25, A-38 and A-39 and more preferably the ring of Formula A-1.

A C1 to C6 alkyl group which may be substituted with a halogen atom, which Y represents, is an alkyl group having 1 to 6 carbon atoms, which is chained, branched, cyclic or combination thereof, and the upper limit of the number of halogen atoms which may be substituted Is the number of hydrogen atoms which the alkyl group has. When a branched or cyclic alkyl group is included, it is obvious that the number of carbons is 3 or more.

Spécifie examples of a C1 to C6 alkyloxy group which may be substituted with a halogen atom* which Y represents include a methoxy group, an ethoxy group, a trifluoromethyloxy group and a difluoromethyloxy group.

A preferred aspect of Y is preferably a hydrogen atom or a halogen atom and more preferably a hydrogen atom.

A preferred aspect of R is a group represented by the Formula (a), (c) and (d) described above.

in Formula (I), a substituted C1 to C6 alkyl group which R1 represents is an alkyl group having 1 to 6 carbon atoms, which Is chained, branched, cyclic or combination thereof, and the upper limit of the number of substituted substituents Is the number of hydrogen atoms which the alkyl group has. Examples of the substituted substituent include a halogen atom, a hydroxyl group, a cyano group, a nitro group, a phenyl group (this phenyl group may be substituted wîth a C1 to C4 alkyl group which may be substituted with a halogen, a C1 to 04 alkyloxy group which may be substituted with a halogen, a hydroxyl group, or a halogen atom), a phenoxy group (this phenyl group may be substituted with a C1 to 04 alkyl group which may be substituted with a halogen, a C1 to 04 alkyloxy group which may be substituted with a halogen, a hydroxyl group, or a halogen atom), a benzyloxy group (the phenyl group in this benzyloxy group may be substituted with a C1 to 04 alkyl group which may be substituted with a halogen, a C1 to 04 alkyloxy group which may be substituted with a halogen, a hydroxyl group, or a halogen atom), and the like. Spécifie examples thereof include a 1,1,141 trifluoroethyl group, a trifluoromethyl group, a trichloromethyl group, a difluorochloromethyl group, a difluoromethyl group, a dichloromethyl group, a dibromomethyl group, a chloromethyl group, a difluoroethyl group, a dichloroethyl group, a 2,2,2-trifluoroethyl group, a pentafluoroethyl group, a difluorocyclopropyl group, a 2-cyanoethyl group, a 2-nitroethyl group and the like. A 1,1,1-trifluoroethyl group, a trifluoromethyl group, a difluorochloromethyl group, a difluoromethyl group and a pentafluoroethyt group are preferred, a trifluoromethyl group, a difluorochloromethyl group, a difluoromethyl group and a pentafluoroethyt group are more preferred, and a trifluoromethyl group are particularly preferred.

ln Formula (l), a C1 to C6 alkyl group which may be substituted with a halogen atom which R3, R5, R7, Ry, and Rz represent Is an alkyl group having 1 to 6 carbon atoms, which is chained, branched, cyclic or combination thereof, and the upper limit of the number of substituted halogen atoms is the number of hydrogen atoms which the alkyl group has. When a branched or cyclic alkyl group Is Induded, It Is obvious that the number of carbons Is 3 or more. Spécifie examples thereof Include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a t-butyl group, a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, a trifluoromethyl group, a trichloromethyl group, a difluorochloromethyl group, a difluoromethyl group, a dichloromethyl group, a dibromomethyl group, a chloromethyl group, a difluoroethyl group, a dichloroethyl group, a 2,2,2-trifluoroethyl group, a pentafluoroethyt group, a difluorocyclopropyl group, a trifluoroisopropyl group, and a hexafluoroisopropyl group, and the like.

R3 is each preferably an ethyl group, an isopropyl group, a cyclopropyl group, a trifluoromethyl group, a difluorochloromethyl group, a difluoromethyl group and a pentafluoroethyl group, more preferably a trifluoromethyl group, a difluorochloromethyl group, a difluoromethyl group and a pentafluoroethyl group, and particularly preferably a trifluoromethyl group. R5 is preferably a trifluoromethyl group, a trichloromethyl group, a dichloromethyl group, a difluoromethyl group, a difluorochloromethyl group, a chloromethyl group and a pentafluoroethyl group, more preferably a trifluoromethyl group, a difluoromethyl group, a difluorochloromethy! group and a pentafluoroethyl group, and particularly preferably a trifluoromethyl group. R7 Is preferably a trifluoromethyl group, a trichloromethyl group, a dichloromethyi group, a difluoromethyi group, a difluorochloromethy! group, a chloromethyi group and a pentafluoroethyl group, more preferably a trifluoromethy! group, a difluoromethyi group, a difluorochloromethy! group and a pentafluoroethyl group, and particularly preferably a trifluoromethyl group.

Ry Is preferably a methyl group, ethyl group, propyl group or Isopropyl group. Rz is preferably a methyl group or trifluoromethy! group.

A C1 to C6 alkyl group which may be substituted with a halogen atom, which R2 represents, Is an alkyl group having 1 to 6 carbon atoms, which Is chained, branched, cyclic or combination thereof, and the upper limit of the number of substituted halogen atoms Is the number of hydrogen atoms which the alkyl group has. When a branched or cyclic alkyl group Is included, It Is obvlous that the number of carbons Is 3 or more. Spécifie examples thereof Include a trifluoromethyl group, a trichloromethyl group, a difluorochloromethy! group, a difluoromethyi group, a dichloromethyi group, a dibromomethy! group, a chloromethyi group, a difluoroethyl group, a dlchloroethyl group, a 2,2,2-trifluoroethyl group, a pentafluoroethyl group, a difluorocyclopropyl group, a 1-(trifluoromethyl)ethyl group, a l-trifluoromethyl-2,2,2trifluoroethyl group, a pentafluoroethyl group, and a difluorocyclopropyl group, and the like, and preferred examples thereof include a 2,2,2-trifluoroethyl group, a 1-(trifluoromethyl)ethyl group and a 1-trifluoromethyl-2,2,2-trifluoroethyl group.

AC1 to C6 alkyl group which may be substituted which R4 and R6 represent is an alkyl group having 1 to 18 carbon atoms, which is chained, branched, cyclic or combination thereof, and the upperlimit ofthe numberof substituents which maybe substituted Is the number of hydrogen atoms which the alkyl group has. When a branched or cyclic alkyl group is included, It is obvlous that the number of carbons Is 3 or more. Examples of the substituent which may be substituted include a halogen atom, a hydroxyl group, a cyano group, a nitro group and the like. Spécifie examples thereof include a methyl group, an ethyl group, an n propyl group, an Isopropyl group, an n-butyl group, an s-butyl group, a t-butyl group, a 3methyl-2-butyl group, a 3-pentyl group, a 4-heptyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, an n-octyl group, an n-tridecyl group, an nhexadecyl group, an n-octadecyl group, a trifluoromethyi group, a trichloromethyl group, a difluorochloromethyl group, a difluoromethyl group, a dichloromethyl group, a dibromomethyl group, a chloromethyl group, a difiuoroethyl group, a dichloroethyl group, a 2,2,2-trifluoroethyl group, a pentafluoroethyl group, a difluorocyclopropyl group, a 2-hydroxyethyl group, a 2hydroxy-n-propyl group, a 3-hydroxy-n-propyl group, a 2,3-dihydroxy-n-propyl group, a cyanomethyl group, a 2-cyanoethyl group, a 2-nltroethyl group and the like.

R4 Is each preferably a methyl group, an ethyl group, a 2,2,2-trifluoroethyl group, a 2,2dlfluoroethyl group, an n-propyl group, an Isopropyl group, a cyclopropyl group, a t-butyl group, a cyclopentyl group, a cyclohexyl group and a 2-hydroxyethyl group, and more preferably a methyl group, an ethyl group and a cyclopropyl group. R6 is preferably a methyl group, an ethyl group, an isopropyl group a cyclopropyl group, a t-butyl group and a cyanomethyl group, and more preferably a methyl group, an ethyl group, a cyclopropyl group and a t-butyl group.

A C1 to C6 alkyl group which may be substituted with a halogen atom, which R4a, R4b, R4c, R4d, R4e, R4f, R6a, R6b, R6c, R6d, R6e, R6f, R6g, R6h, R6I, R6j and R6k represent, Is an alkyl group having 1 to 6 carbon atoms, which Is chained, branched, cyclic or combination thereof, and the upper lîmlt of the number of substituted halogen atoms is the number of hydrogen atoms which the alkyl group has. When a branched or cyclic alkyl group is inciuded, It Is obvious that the number of carbons is 3 or more. Spécifie examples thereof include a methyl group, an ethyl group, an n-propyl group, an Isopropyl group, an n-butyl group, a t-butyl group, a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, a trifluoromethyi group, a trichloromethyl group, a difluorochloromethyl group, a difluoromethyl group, a dichloromethyl group, a dibromomethyl group, a chloromethyl group, a difiuoroethyl group, a 2-chloroethyl group, a dichloroethyl group, a 2,2,2-trifluoroethyl group, a pentafluoroethyl group, a difluorocyclopropyl group and the like. R6a is preferably a methyl group, an ethyl group, an isopropyl group and a cyclopropyl group. R6b Is preferably a methyl group.

A C2 to C6 alkenyl group which may be substituted with a halogen atom, which R1, R2, R3, R4, R4a, R4b, R4c, R4d, R4e, R4f, R5, R6, R6a, R6b, R6c, R6d, R6e, R6f, R6g, R6h, R6i, R6j, R6k, R7, Ry and Rz represent, is an alkenyl group having 2 to 6 carbon atoms, which Is chained, branched, cyclic or combination thereof, and the upper limit of the number of substituted halogen atoms Is the number of hydrogen atoms which the alkenyl group has. When a branched or cydic alkenyl group Is included, It is obvious that the number of carbons is 3 or more. Spécifie examples thereof include an ethenyl group, a 1-propenyl group, a 2propenyl group, a 2-fluoro-1-propenyl group, a 2-methyl-1-propenyl group and the iike, and preferred examples thereof include an ethenyl group.

A C2 to C6 alkynyl group which may be substituted with a halogen atom, which R1, R2, R3, R4, R4a, R4b, R4c, R4d, R4e, R4f, R5, R6, R6a, R6b, R6c, R6d, R6e, R6f, R6g, R6h, R6I, R6j, R6k, R7, Ry and Rz represent, Is an alkynyl group having 2 to 6 carbon atoms, which Is chained, branched, cyclic or combination thereof, and the upper limit of the number of substituted halogen atoms is the number of hydrogen atoms which the alkynyl group has. When a branched or cyclic alkynyl group Is Included, it is obvious that the number of carbons is 3 or more. Spécifie examples thereof Include a 1-propynyl group, a 2-propynyl group, a 1butynyl group, a 2-butynyl group, a 1-pentynyl group, a 2-pentynyl group, a 3-pentynyl group and the like, and preferred examples thereof include a 1-propynyl group, a 2-propynyl group and a 2-butynyl group.

The (C6 to C10) aryl of a substituted or unsubstituted (06 to 010) aryl group, a substituted or unsubstituted (06 to C10) aryl (C1 to C6) alkyl group, a substituted or unsubstituted (C6 to C10) aryl (02 to 06) alkenyl group and a substituted or unsubstituted (06 to 010) aryl (02 to 06) alkynyl group, which R3, R4, R4a, R4b, R4c, R5, R6, R6a, R6b, R6c, R7, Ry and Rz represent, specifically représente a phenyl group and a naphthyl group, and the (01 to 06) alkyl group, the (02 to 06) alkenyl group and the (02 to 06) alkynyl group may hâve a straight chain, branch or ring. Examples of the substituent which may be substituted with an aryl group Inciude a halogen atom, a C1 to C4 alkyl group which may be substituted with halogen, a C1 to C4 alkyloxy group which may be substituted with halogen, a C3 to C6 cyclic alkyl group, a methylsulfonyl group, a methoxy group, a nitro group, a cyano group and the like. Spécifie examples thereof inciude a phenyl group, a benzyl group, a 2-phenylethyl group, a 2-phenylethenyl group, a 2-phenylethynyl group, a 4-methylphenyl group, a 2cyanophenyl group, a 3-chlorophenyl group, a 4-methoxyphenyl group, a 3-cyanophenyl group, 1,1-diphenylmethyl group, a naphthylethyl group, a naphthylpropyl group and the like, and preferred examples thereof inciude a benzyl group and a 2-phenylethyl group, a naphthylethyl group, a naphthylpropyl group.

The (C1 to C6) alkyl group, (C2 to C6) alkenyl group and (C2 to C6) alkenyl group of a substituted or unsubstituted phenoxy (C1 to C6) alkyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkenyl group and a substituted or unsubstituted phenoxy (C2 to C6) alkynyl group, which R3, R4, R4a, R4b, R4c, R5, R6, R6a, R6b, R6c, R7, Ry and Rz represent, may hâve a straight chain, branch or ring. Examples of the substituent which may be substituted with a phenoxy group inciude a halogen atom, a C1 to C4 alkyl group which may be substituted with halogen, a C1 to C4 alkyloxy group which may be substituted with halogen, a C3 to C6 cyclic alkyl group, a methylsulfonyl group, a methoxy group, a nitro group, a cyano group and the like. Spécifie examples thereof inciude a phenoxy group, a phenoxymethyl group, a 2-phenoxyethyl group, a 2-phenoxyethenyl group, a 2phenoxyethynyl group, a 4-chlorophenoxy group, a 2-methylphenoxy group and the like, and preferred examples thereof inciude a 2-phenoxyethyl group.

The 5- to 10-membered heterocycie of a substituted or unsubstituted 5- to 10membered heterocycie, a substituted or unsubstituted 5- to 10-membered heterocycie (C1 to C6) alkyl group, a substituted or unsubstituted 5- to 10-membered heterocycie (C2 to C6) alkenyl group and a substituted or unsubstituted 5- to 10-membered heterocycie (C2 to C6) alkynyl group, which R3, R4, R4a, R4b, R4c, R5, R6, R6a, R6b, R6c, R7, Ry and Rz represent, represents a ring including a hetero atom, such as an oxygen atom, a sulfur atom or a nitrogen atom as an atom constituting 1 to 4 rings, and examples thereof inciude a furanyl group, a thienyl group, a pyridyl group, a pyrroiidinyl group, a piperidinyt group, a piperazinyl group, a pyrimidinyl group, a morpholinyt group, a thiazolyl group, an Imidazolyt group, a triazolyi group, a tetrahydrofurany! group, a quinolinyl group and the like. Examples of the substituent which may be substituted with a heterocycle include a halogen atom, a C1 to 04 alkyl group which may be substituted with halogen, a C1 to 04 alkyloxy group which may be substituted with halogen, a C3 to C6 cyclic alkyl group, a methytsulfonyl group, a methoxy group, a nitro group, a cyano group and the iike. The (C1 to 06) alkyl group, (02 to 06) alkenyl group and (02 to 06) alkenyl group may hâve a straight chain, branch or ring. Spécifie examples thereof include a 2-pyridyt group, a 3-pyridyl group, a 4-pyridyl group, a 2pyridylmethyt group, a 3-pyridytmethyt group, a 4-pyridylmethyl group, a 2-(4-pyridyl)ethenyl group, a 2-(4-pyridyl)ethyny1 group, a 2-furanylmethyl group, a 2-thienylmethyl group, a 2tetrahydrofuranylmethyl group and the like, and preferred examples thereof include a 2pyridylmethyl group, a 3-pyridylmethyt group, a 4-pyridytmethyt group, a 2-furanylmethyl group, a 2-thienylmethyl group and a 2-tetrahydrofuranylmethyl group.

The (C1 to 04) alkoxy of a (C 1 to 04) alkoxy (C1 to 05) alkyl group, a (C1 to 04) alkoxy (02 to 05) alkenyl group and a (C1 to 04) alkoxy (02 to 05) alkynyl group, which R3, R4, R4a, R4b, R4c, R5, R6, R6a, R6b, R6c, R6e, R6f, R7 and Rz represent, represents a (C1 to 04) alkyloxy, alkenytoxy and alkynytoxy having a straight chain, branch or ring. Spécifie examples thereof include a methoxymethyl group, a 2-methoxyethyl group, an ethoxymethyl group, a 2-ethoxyethyl group, a 3-methoxy-2-propenyt group, a 3-methoxy-2-propyny1 group and the like. R4 Is preferably a 2-methoxyethyl group.

The (C1 to 04) alkylthio of a (C1 to 04) alkylthio (C1 to 05) alkyl group, a (C1 to 04) alkylthio (02 to 05) alkenyl group and a (01 to 04) alkylthio (02 to 05) alkynyl group, which R3, R4, R4a, R4b, R4c, R5, R6, R6a, R6b, R6c, R6e, R6f, R7 and Rz represent, represents a (C1 to 04) alkylthio, alkenylthio and alkynylthio having a straight chain, branch or ring. Examples thereof Include a methylthiomethyt group, a 2-methylthioethyt group, an ethylthlomethyl group, a 2-ethylthioethyl group, a 3-methylthio-2-propenyl group, a 3methylthîo-2-propynyl group and the like. R4 ls preferably a 2-methylthioethyl group.

The (C6 to C10) aryl of “a substituted or unsubstituted (C6 to C10) aryl group, which R2, R4d, R4e, R4f, R6d, R6e, R6f, R6g, R6h, R6I, R6j and R6k represent, specifically represents a phenyl group and a naphthyl group, and the (C1 to C6) alkyl group, (C2 to C6) alkenyl group and (C2 to C6) alkenyl group may hâve a straight chain, branch or ring. Examples of the substituent which may be substituted with an aryl group Include a halogen atom, a C1 to C4 alkyl group which may be substituted with halogen, a C1 to C4 alkyloxy group which may be substituted with halogen, a C3 to C6 cyclic alkyl group, a methylsulfonyl group, a methoxy group, a nitro group, a cyano group and the like. Spécifie examples thereof Include a phenyl group, a 2-methylphenyl group, a 3-methoxyphenyl group, a 4-nitrophenyl group, a 4cyanophenyl group and the like.

The 5- to 10-membered heterocycle of a substituted or unsubstituted 5- to 10membered heterocycle, which R2, R4d, R4e, R4f, R6d, R6e, R6f, R6g and R6h represent, represents a ring Including a hetero atom, such as an oxygen atom, a sulfur atom or a nitrogen atom as an atom constitutïng 1 to 4 rings, and examples thereof include a furanyl group, a thienyl group, a pyridyl group, a pyrrolidinyl group, a piperidinyl group, a piperazinyl group, a pyrimidinyl group, a morpholinyl group, a thiazolyl group, an imidazolyl group, a triazolyl group, a tetrahydrofuranyl group, a quinoiinyl group and the like. Examples of the substituent which may be substituted with a heterocycle Include a halogen atom, a C1 to C4 alkyl group which may be substituted with halogen, a C1 to C4 alkyloxy group which may be substituted with halogen, a C3 to C6 cyclic alkyl group, a methylsulfonyl group, a methoxy group, a nitro group, a cyano group and the like. Spécifie examples thereof include a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 2-furanyl group, a 2-thienyl group, a 2-tetrahydrofuranyl group and the like.

As a preferred aspect of a compound represented by Formula (I),

R represents the following Formula (a), [Chemical Formula 38], —C-R, o

(a)

Ar represents a 6-chloro-3-pyridyl group, a 2-chloro-5-thiazolyl group, a 6-chloro-5fluoro-3-pyridy! group, a 6-fluoro-3-pyridy! group, a 6-bromo-3-pyridyl group, a 2-chloro-5pyrimidinyl group, a 6-trifluoromethy!-3-pyridyl group and a 2-chloro-5-pyrimidiny! group,

A represents a ring represented by A-1, A-13, A-14, A-15, A-16, A-23 and A-38,

Y represents a hydrogen atom and a 3-cyano group, and

R1 represents a trifluoromethyl group, a difluoromethyl group, a chlorodifluoromethyl group, a pentafluoroethyl group, a trifluoroethyl group, an ethenyl group and a 2-propynyl group.

As another preferred aspect of a compound represented by Formula (I),

R represents the following Formula (c), [Chemical Formula 39]

-ç-_Ri s

(c)

Ar represents a 6-chloro-3-pyridy! group, a 2-chloro-5-thiazolyl group, a 6-chloro-5fluoro-3-pyridyl group, a 6-fluoro-3-pyridy! group, a 6-bromo-3-pyridyl group, a 2-chloro-5pyrimldy! group and a 6-trifluoromethy!-3-pyridyl group,

A represents a ring represented byA-1,

Y represents a hydrogen atom, and

R3 represents a trifluoromethyl group, a difluoromethyl group, a chlorodifluoromethyl group and a pentafluoroethyl group.

As still another preferred aspect of a compound represented by Formula (I),

R represents the following Formula (d), [Chemical Formula 40]

K.

(d)

Ar represents a 6-chlora-3-pyridyl group, a 6-chloro-5-fluoro-3-pyridyl group, a 6-fluoro3-pyrldyl group, a 6-bromo-3-pyridyl group and a 2-chloro-5-pyrimidyl group,

A représente a ring represented by A-1,

Y represents a hydrogen atom,

R4 représente a hydrogen atom, a methyl group, an ethyi group, an n-propyl group, an Isopropyl group, a cyclopropyl group, a cyclobutyl group, a cyclohexyl group, and cyclopentyl group, and

R5 represents a trifluoromethyl group, a difluoromethyl group, a chlorodifluoromethyl group and a pentafluoroethyl group.

As yet another preferred aspect of a compound represented by Formula (I),

R représente the following Formula (e) group [Chemical Formula 41] —ç-r?

N ôr# ( e )

Ar représente a 6-chloro-3-pyridyl group, a 6-chloro-5-fluoro-3-pyridyl group, a 6-fluoro3-pyridyl group, a 6-bromo-3-pyridyl group and a 2-chloro-5-pyrimldyl group,

A représente a ring represented byA-1,

Y represents a hydrogen atom, and

R6 représente a hydrogen atom, a methyl group, an ethyi group, a 2-propenyl group, a methylcarbonyl group, an ethylcarbonyl group, a cyclopropylcarbonyl group, an ethenylcarbonyl group, a 2-propynylcarbonyl group, a benzoyl group, a 3-pyridylcarbonyl group, a methyloxycarbonyl group and a phenyloxycarbonyl group, and

R7 représente a trifluoromethyl group, a difluoromethyl group, a chlorodifluoromethyl group and a pentafluoroethyl group.

Spécifie examples of the compound of Formula (I) include a compound represented by a combination of the following Table A and Table B.

[Table 1-1]

Table A

	Compoun d No.	Ar	A	Y	R
Table 1	1-5-1- 710	6-Chloro-3-pyrldyl	A1	H	represents a combination of substituents corresponding to each row of Nos. (1 and 6) below of Table B
Table 2	2-1-2- 710	2-Chloro-5thlazolyi	A- 1	H	represents a combination of substituents corresponding to each row of Table B
Table 3	3-2-3- 710	6-Fluoro-3-pyrldyl	A1	H	represents a combination of substituents corresponding to each row of Nos. (1 and 3) below of Table B
Table 4	4-2-4- 710	6-Bromo-3-pyridyl	A1	H	represents a combination of substituents corresponding to each row of Nos. (1 and 3) below of Table B
Table 5	5-2-5- 710	6-Chloro-5-fluoro- 3-pyrldyl	A- 1	H	represents a combination of substituents corresponding to each row of Nos. (1 and 3) below of Table B
Table 6	6-2-6- 710	2-Chloro-5pyrimldinyl	A1	H	represents a combination of substituents corresponding to each row of Nos. (1 and 3) below of Table B

[Table 1-2]

Table 7	7-1-7- 710	5-Chloropyrazln-2y!	A1	H	represents a combination of substituents corresponding to each row of Table B
Table 8	8-1-8- 710	6-Chloropyridazin- 3-yl	A- 1	H	represents a combination of substituents corresponding to each row of Table B
Table 9	9-1 -9- 710	2-Chloro-5oxazolyl	A1	H	represents a combination of substituents corresponding to each row of Table B

Table 10	10-1-10- 710	6-trlfluoromethyl3-pyridyl	A1	H	represents a combination of substituents corresponding to each row of Table B
Tabie 11	11-1-11- 710	3-tetrahydrofuranyl	A- 1	H	represents a combination of substituents corresponding to each row of Table B
Table 12	12-1-12- 710	2-Chloro-4-pyridyl	A1	H	represents a combination of substituents corresponding to each row of Tabie B
Table 13	13-1-13- 710	3-Cyanophenyl	A- 1	H	represents a combination of substituents corresponding to each row of Table B
Table 14	14-1-14- 710	6-Chloro-3-pyrldyl	A- 1	3F	represents a combination of substituents corresponding to each row of Table B
Table 15	15-1-15- 710	2-Chloro-5thlazolyl	A1	3F	represents a combination of substituents corresponding to each row of Table B

[Table 1-3]

Table 16	16-1-16- 710	6-Fluoro-3-pyridyl	A1	3F	represents a combination of substituents corresponding to each row of Table B
Table 17	17-1-17- 710	6-Bromo-3-pyridyl	A- 1	3F	represents a combination of substituents corresponding to each row of Tabie B
Table 18	18-1-18- 710	6-Chloro-5-fluoro- 3-pyridyi	A1	3F	represents a combination of substituents corresponding to each row of Table B
Table 19	19-1-19- 710	2-Chloro-5pyrimidinyl	A- 1	3F	represents a combination of substituents corresponding to each row of Table B
Table 20	20-1-20- 710	5-Chloropyrazln-2yi	A- 1	3F	represents a combination . of substituents corresponding to each row of Table B
Tabie 21	21-1-21- 710	6-Chloropyridazin- 3-yl	A1	3F	represents a combination of substituents corresponding to each row of Table B

Table 22	22-1-22- 710	2-Chloro-5oxazolyl	A1	3F	represents a combination of substituents corresponding to each row of Table B
Table 23	23-1-23- 710	6-trifluoromethyl3-pyridyl	A- 1	3F	represents a combination of substituents corresponding to each row of Table B
Table 24	24-1-24- 710	3-tetrahydrofuranyi	A1	3F	represents a combination of substituents corresponding to each row of Table B

[Table 1-4]

Table 25	25-1-25- 710	6-Chloro-3-pyridyl	A- 1	4F	represents a combination of substituents corresponding to each row of Table B
Table 26	26-1-26- 710	2-Chloro-5thiazolyl	A- 1	4F	represents a combination of substituents corresponding to each row of Table B
Table 27	27-1-27- 710	6-Fluoro-3-pyridyl	A- 1	4F	represents a combination of substituents corresponding to each row of Table B
Table 28	28-1-28- 710	6-Bromo-3-pyridyi	A1	4F	represents a combination of substituents corresponding to each row of Table B
Table 29	29-1-29- 710	6-Chloro-5-fluoro- 3-pyridyl	A- 1	4F	represents a combination of substituents corresponding to each row of Table B
Table 30	30-1-30- 710	2-Chloro-5pyrimidinyl	A- 1	4F	represents a combination of substituents corresponding to each row of Table B
Table 31	31-1-31- 710	5-Chloropyrazin-2yi	A1	4F	represents a combination of substituents corresponding to each row of Table B
Table 32	32-1-32- 710	6-Chloropyrldazin- 3-yl	A- 1	4F	represents a combination of substituents corresponding to each row of Table B

[Table 2-1]

Table A

	Compoun d No.	Ar	A	Y	R
Table 33	33-1-33- 710	2-Chloro-5oxazolyi	A- 1	4- F	represents a combination of substituents corresponding to each row of Table B
Table 34	34-1-34- 710	6-trlfluoromethyl-3pyrldyl	A- 1	4- F	represents a combination of substituents corresponding to each row of Table B
Table 35	35-1-35- 710	3-tetrahydrofuranyl	A- 1	4- F	represents a combination of substituents corresponding to each row of Table B
Table 36	36-1-36- 710	6-Chloro-3-pyridyl	A- 1	5- F	represents a combination of substituents corresponding to each row of Table B

[Table 2-2]

Table 37	37-1-37- 710	2-Chloro-5thlazolyl	A- 1	5- F	represents a combination of substituents corresponding to each row of Table B
Table 38	38-1-38- 710	6-Fluoro-3-pyridyl	A- 1	5F	represents a combination of substituents

					corresponding to each row of Table B
Table 39	39-1-39- 710	6-Bromo-3-pyridyl	A- 1	5- F	represents a combination of substituents corresponding to each row of Table B
Table 40	40-1-40- 710	6-Chloro-5-fluoro- 3-pyridyi	A- 1	5- F	represents a combination of substituents corresponding to each row of Table B

[Table 2-3]

Table 41	41-1-41- 710	2-Chloro-5pyrimldlnyl	A- 1	5F	represents a combination of substituents corresponding to each row of Table B
Table 42	42-1-42- 710	5-Chloropyrazin-2- yi	A- 1	5F	represents a combination of substituents corresponding to each row of Table B
Table 43	43-1-43- 710	6-Chloropyridazln- 3-yl	A- 1	5- F	represents a combination of substituents corresponding to each row of Table B
Table 44	44-1-44- 710	2-Chloro-5oxazolyl	A- 1	5F	represents a combination of substituents corresponding to each

row of Table B

[Table 2-4]

Table 45	45-1-45- 710	6-trifiuoromethyl-3pyridyl	A- 1	5- F	represents a combination of substituents corresponding to each row of Table B
Table 46	46-1-46- 710	3-tetrahydrofuranyl	A- 1	5F	represents a combination of substituents corresponding to each row of Table B
Table 47	47-1-47- 710	6-Ch!oro-3-pyridyi	A- 1	6- F	represents a combination of substituents corresponding to each row of Table B
Table 48	48-1-48- 710	2-Chloro-5thlazolyl	A- 1	6- F	represents a combination of substituents corresponding to each row of Table B

[Table 2-5]

Table 49	49-1-49- 710	6-Fluoro-3-pyrldyl	A- 1	6- F	represents a combination of substituents corresponding to each row of Table B
Table 50	50-1-50- 710	6-Bromo-3-pyridyl	A- 1	6- F	represents a combination of substituents corresponding to each

					row of Table B
Table 51	51-1-51- 710	6-Chloro-5-fiuoro- 3-pyridyl	A- 1	6- F	represents a combination of substituants corresponding to each row of Table B
Table 52	52-1-52- 710	2-Chloro-5pyrimidinyl	A- 1	6- F	represents a combination of substltuents corresponding to each row of Table B

[Table 2-6]

Table 53	53-1-53- 710	5-Chloropyrazin-2- yi	A- 1	6F	represents a combination of substltuents corresponding to each row of Table B
Table 54	54-1-54- 710	6-Chloropyridazin- 3-yl	A- 1	6- F	represents a combination of substltuents corresponding to each row of Table B
Table 55	55-1-55- 710	2-Chloro-5oxazolyl	A- 1	6- F	represents a combination of substituents corresponding to each row of Table B
Table 56	56-1-56- 710	6-trifiuoromethyi-3- pyridyi	A- 1	6- F	represents a combination of substituents corresponding to each row of Table B

[Table 2-7]

Table 57	57-1-57- 710	3-tetrahydrofuranyl	A- 1	6- F	represents a combination of substituents corresponding to each row of Table B
Table 58	58-1-58- 710	6-Chloro-3-pyridyl	A- 1	3- Cl	represents a combination of substituents corresponding to each row of Table B
Table 59	59-1-59- 710	2-Chloro-5thlazolyl	A- 1	3- Cl	represents a combination of substituents corresponding to each row of Table B
Table 60	60-1-60- 710	6-Fluoro-3-pyrldyi	A- 1	3- Cl	represents a combination of substituents corresponding to each row of Table B

[Table 2-8]

Table 61	61-1-61- 710	6-Bromo-3-pyrldyi	A- 1	3- Cl	represents a combination of substituents corresponding to each row of Table B
					represents a combination
Table	62-1-62-	6-Chloro-5-fluoro-	A-	3-	of substituents
62	710	3-pyrldyl	1	Cl	corresponding to each row of Table B

Table 63	63-1-63- 642	2-Chloro-5pyrimidinyi	A- 1	3- Cl	represents a combination of substituents corresponding to each row of Table B
Table 64	64-1-64- 710	5-Chloropyrazln-2- yi	A- 1	3- Cl	represents a combination of substituents corresponding to each row of Table B

[Table 3-1]

Table A

	Compou nd No.	Ar	A	Y	R
Table 65	65-1-65- 710	6-Chloropyrldazln- 3-yl	A- 1	3Cl	represents a combination of substituents corresponding to each row of Table B
Table 66	66-1-66- 710	2-Chloro-5oxazolyl	A- 1	3Cl	represents a combination of substituents corresponding to each row of Table B
Table 67	67-1-67- 710	6-trlfiuoromethyl-3pyrldyi	A- 1	3Cl	represents a combination of substituents corresponding to each row of Table B
Table 68	68-1-68- 710	3-tetrahydrofuranyl	A1	3Cl	represents a combination of substituents corresponding to each row of Table B
Table 69	69-1-69- 710	6-Chloro-3-pyrldyl	A1	4C!	represents a combination of substituents corresponding to each row of Table B
Table 70	70-1-70- 710	2-Chloro-5thiazolyl	A- 1	4- Cl	represents a combination of substituents corresponding to each row of Table B
Table 71	71-1-71- 710	6-Fluoro-3-pyrldyl	A- 1	4Cl	represents a combination of substituents corresponding to each row

of Table B [Table 3-2]

Table 72	72-1-72- 710	6-Bromo-3-pyrldy!	A- 1	4Cl	represents a combination of substituents correspondîng to each row of Table B
Table 73	73-1-73- 710	6-Chloro-5-fluoro3-pyrldy!	A1	4Cl	represents a combination of substituents correspondîng to each row of Table B
Table 74	74-1-74- 710	2-Ch!oro-5pyrlmidlnyl	A1	4Cl	represents a combination of substituents correspondîng to each row of Table B
Table 75	75-1-75- 710	5-Chloropyrazin-2yi	A1	4C!	represents a combination of substituents corresponding to each row of Table B
Table 76	76-1-76- 710	6-Chloropyridazin- 3-yl	A1	4C!	represents a combination of substituents correspondîng to each row of Table B
Table 77	77-1-77- 710	2-Chloro-5oxazolyl	A- 1	4C!	represents a combination of substituents corresponding to each row of Table B
Table 78	78-1-78- 710	6-trlf!uoromethyl-3pyridyl	A- 1	4Cl	represents a combination of substituents corresponding to each row of Table B
Table 79	79-1-79- 710	3-tetrahydrofuranyl	A- 1	4Cl	represents a combination of substituents corresponding to each row of Table B
Table 80	80-1-80- 710	6-Chloro-3-pyrldyl	A- 1	5Cl	represents a combination of substituents corresponding to each row of Table B

[Table 3-3]

Table 81	81-1-81- 710	2-Chloro-5thiazolyl	A- 1	5Cl	represents a combination of substituents corresponding to each row of Table B
Table 82	82-1-82- 710	6-Fluoro-3-pyridyl	A1	5Cl	represents a combination of substituents corresponding to each row of Table B
Table	83-1-83-	6-Bromo-3-pyridyl	A-	5-	represents a combination

83	710		1	Cl	of substîtuents corresponding to each row of Table B
Table 84	84-1-84- 710	6-Chloro-5-fluoro- 3-pyridyl	A1	δει	represents a combination of substîtuents corresponding to each row of Table B
Table 85	85-1-85- 710	2-Chloro-5pyrlmidinyl	A1	βει	represents a combination of substîtuents corresponding to each row of Table B
Table 86	86-1-86- 710	5-Chloropyrazin-2yi	A- 1	5Cl	represents a combination of substituants corresponding to each row of Table B
Table 87	87-1-87- 710	6-Chloropyrldazln- 3-yl	A- 1	5Cl	represents a combination of substituants corresponding to each row of Table B
Table 88	88-1-88- 710	2-Chloro-5oxazolyl	A- 1	5Cl	represents a combination of substituants corresponding to each row of Table B
Table 89	89-1 -89- 710	6-trifluoromethyl-3pyrtdyl	A- 1	5Cl	represents a combination of substituants corresponding to each row of Table B

[Table 3-4]

Table 90	90-1-90- 710	3-tetrahydrofuranyl	A- 1	5Cl	represents a combination of substituants corresponding to each row of Table B
Table 91	91-1-91- 710	6-Chloro-3-pyridyl	A- 1	6Cl	represents a combination of substituents corresponding to each row of Table B
Table 92	92-1-92- 710	2-Chloro-5thlazolyl	A1	6Cl	represents a combination of substituents corresponding to each row of Table B
Table 93	93-1-93- 710	6-Fluoro-3-pyrldyl	A- 1	6Cl	represents a combination of substituents corresponding to each row of Table B
Table 94	94-1-94- 710	6-Bromo-3-pyrldyl	A- 1	6Cl	represents a combination of substituents corresponding to each row of Table B
Table 95	95-1-95- 710	6-Chloro-5-fluoro- 3-pyrldyl	A- 1	6Cl	represents a combination of substituents corresponding to each row

					of Table B
Table 96	96-1-96- 710	2-Chloro-5pyrlmid Inyl	A1	6Cl	represents a combination of substituents corresponding to each row of Table B

[Table 4-1]

Table A

	Compou nd No.	Ar	A	Y	R
Table 97	97-1-97- 710	5-Chloropyrazln-2yi	A1	6Cl	represents a combination of substituents corresponding to each row of Table B
Table 98	98-1-98- 710	6-Chioropyridazin- 3-yl	A1	6Ci	represents a combination of substituents corresponding to each row of Table B
Table 99	99-1-99- 710	2-Chloro-5oxazolyl	A1	6Cl	represents a combination of substituents corresponding to each row of Table B
Table 100	1001-100710	6-trifiuoromethyl-3pyrldyl	A1	6Cl	represents a combination of substituents corresponding to each row of Table B
Table 101	1011-101710	3-tetrahydrofuranyl	A- 1	6Cl	represents a combination of substituents corresponding to each row of Table B
Table 102	1021-102710	6-Chloro-3-pyridyl	A1	3CN	represents a combination of substituents corresponding to each row of Table B
Table 103	1031-103710	2-Chloro-5thlazolyl	A- 1	3CN	represents a combination of substituents corresponding to each row of Table B
Table 104	1041-104710	6-Fluoro-3-pyrldyl	A- 1	3CN	represents a combination of substituents corresponding to each row of Table B

[Table 4-2]

Table 105

1051-105710

6-Bromo-3-pyridyl

A- 1

3CN

represents a combination of substituents corresponding to each row of Table B

Table 106	1061-106710	6-Chloro-5-fluoro- 3-pyrldyl	A1	3CN	represents a combination of substituants corresponding to each row of Table B
Table 107	1071-107710	2-Chloro-5pyrlmldlnyl	A1	3CN	represents a combination of substituants corresponding to each row of Table B
Table 108	1081-108710	5-Chloropyrazln-2yi	A- 1	3CN	represents a combination of substituants corresponding to each row of Table B
Table 109	1091-109710	6-Chloropyridazin- 3-yl	A1	3CN	represents a combination of substltuents corresponding to each row of Table B
Table 110	1101-110- 710	2-Chloro-5oxazolyl	A- 1	3CN	represents a combination of substltuents corresponding to each row of Table B
Table 111	1111-111710	6-trifluoromethyl-3pyrldyl	A- 1	3CN	represents a combination of substltuents corresponding to each row of Table B
Table 112	1121-112710	3-tetrahydrofuranyi	A1	3CN	represents a combination of substltuents corresponding to each row of Table B
Table 113	1131-113710	6-Chloro-3-pyrldyl	A- 1	4CN	represents a combination of substituents corresponding to each row of Table B

[Table 4-3]

Table 114	1141-114710	2-Chloro-5thiazolyl	A1	4CN	represents a combination of substltuents corresponding to each row of Table B
Table 115	1151—115710	6-Fluoro-3-pyrldyl	A- 1	4CN	represents a combination of substituents corresponding to each row of Table B
Table 116	1161-116710	6-Bromo-3-pyrldyl	A- 1	4CN	represents a combination of substituents corresponding to each row of Table B
Table 117	1171-117710	6-Chloro-5-Fluoro- 3-pyridyl	A1	4CN	represents a combination of substltuents corresponding to each row of Table B

Table 118	1181-118710	2-Chloro-5pyrlmldinyl	A- 1	4CN	represents a combination of substituents corresponding to each row of Table B
Table 119	1191-119710	5-Chloropyrazin-2yi	A- 1	4CN	represents a combination of substituents corresponding to each row of Table B
Table 120	1201-120710	6-Chloropyridazin- 3-yl	A1	4CN	represents a combination of substituents corresponding to each row of Table B
Table 121	1211-121710	2-Chloro-5oxazolyl	A1	4CN	represents a combination of substituents corresponding to each row of Table B
Table 122	1221-122710	6-trifluoromethyl-3pyrldyl	A- 1	4CN	represents a combination of substituents corresponding to each row of Table B

[Table 4-4]

Table 123	1231-123- 710	3-tetrahydrofuranyl	A- 1	4CN	represents a combination of substituents corresponding to each row of Table B
Table 124	1241-124710	6-Chloro-3-pyridyl	A- 1	5CN	represents a combination of substituents corresponding to each row of Table B
Table 125	1251-155710	2-Chloro-5thiazolyl	A- 1	5CN	represents a combination of substituents corresponding to each row of Table B
Table 126	1261-126- 710	6-Fluoro-3-pyrldyl	A1	5CN	represents a combination of substituents corresponding to each row of Table B
Table 127	1271-127- 710	6-Bromo-3-pyridyl	A- 1	5CN	represents a combination of substituents corresponding to each row of Table B
Table 128	1281-128710	6-Chloro-5-fluoro- 3-pyridyl	A- 1	5CN	represents a combination of substituents corresponding to each row of Table B

[Table 5-1]

Table A

	Compou nd No.	Ar	A	Y	R
Table 129	129- 1-129- 710	2-Chloro-5pyrim Idlnyi	A- 1	5- CN	represents a combination of substituents corresponding to each row of Table B
Table 130	130- 1-130- 710	5-Chioropyrazin-2yi	A- 1	5- CN	represents a combination of substituents corresponding to each row of Table B
Table 131	131- 1-131- 710	6-Chloropyridazin- 3-yl	A- 1	5- CN	represents a combination of substituents corresponding to each row of Table B

[Table 5-2]

Table 132	132- 1-132- 710	2-Chloro-5oxazoiyl	A- 1	5- CN	represents a combination of substituents corresponding to each row of Table B
Table 133	133- 1-133- 710	6-trlfluoromethyl-3pyrldyl	A- 1	5- CN	represents a combination of substituents corresponding to each row of Table B
Table 134	134- 1-134-	3-tetrahydrofuranyi	A- 1	5- CN	represents a combination of substituents

	710				corresponding to each row of Table B
Table 135	135- 1-135- 710	6-Chloro-3-pyridyl	A- 1	6- CN	represents a combination of substituents corresponding to each row of Table B

[Table 5-3]

Table 136	136- 1-136- 710	2-Chloro-5- thiazolyl	A- 1	6- CN	represents a combination of substituents corresponding to each row of Table B
Table 137	137- 1-137- 710	6-Fluoro-3-pyrldyl	A- 1	6- CN	represents a combination of substituents corresponding to each row of Table B
Table 138	138- 1-138- 710	6-Bromo-3-pyrldyl	A- 1	6- CN	represents a combination of substituents corresponding to each row of Table B
Table 139	139- 1-139- 710	6-Chloro-5-fluoro- 3-pyridyl	A- 1	6- CN	represents a combination of substituents corresponding to each row of Table B

[Table 5-4]

Table 140	140-1 -140- 710	2-Chloro-5pyrimldlnyl	A- 1	6- CN	represents a combination of substituents corresponding to each row of Table B
Table 141	141- 1-141- 710	5-Chloropyrazin-2- yi	A- 1	6- CN	represents a combination of substituents corresponding to each row of Table B
Table 142	142- 1-142- 710	6-Chloropyrldazin- 3-yl	A- 1	6- CN	represents a combination of substituents corresponding to each row of Table B
Table 143	143- 1-143- 710	2-Chloro-5- oxazolyl	A- 1	6- CN	represents a combination of substituents corresponding to each row of Table B

[Table 5-5]

Table 144	144- 1-144- 710	6-trifluoromethyl-3- pyridyl	A- 1	6- CN	represents a combination of substituents corresponding to each row of Table B
Table 145	145- 1-145- 710	3-tetrahydrofuranyl	A- 1	6- CN	represents a combination of substituents corresponding to each row of Table B
Table	146-	6-Chioro-3-pyridyl	A-	3-	represents a combination of

146	1-146-		1	O	substituents corresponding
	710			H	to each row of Table B
Table 147	147- 1-147- 710	2-Chloro-5thiazolyl	A- 1	3- 0 H	represents a combination of substituents corresponding to each row of Table B

[Table 5-6]

Table 148	148- 1-148- 710	6-Fluoro-3-pyridyl	A- 1	3- O H	represents a combination of substituents corresponding to each row of Table B
Table 149	149- 1-149- 710	6-Bromo-3-pyrldyl	A- 1	3- O H	represents a combination of substituents corresponding to each row of Table B
Table 150	150- 1-150- 710	6-Chloro-5-Fluoro- 3-pyrldyl	A- 1	3- O H	represents a combination of substituents corresponding to each row of Table B
Table 151	151- 1-151- 710	2-Chloro-5pyrimidlnyl	A- 1	3- O H	represents a combination of substituents corresponding to each row of Table B

[Table 5-η

Table 152	152- 1-152- 710	5-Chioropyrazin-2- yi	A- 1	3- O H	represents a combination of substituents corresponding to each row of Table B
Table	153-	6-Chloropyridazin-	A-	3-	represents a combination of
153	1-153-	3-yl	1	O	substituents corresponding

	710			H	to each row of Table B
Table 154	154- 1-154- 710	2-Chloro-5oxazolyl	A- 1	3- 0 H	represents a combination of substituants corresponding to each row of Table B
Table 155	155- 1-155- 710	6-trifluoromethyl-3pyridyl	A- 1	3- 0 H	represents a combination of substituents corresponding to each row of Table B

[Table 5-8]

Table 156	156- 1-156- 710	3-tetrahydrofuranyl	A- 1	3- OH	represents a combination of substituents corresponding to each row of Table B
Table 157	157- 1-157- 710	6-Chloro-3-pyridyl	A- 1	4- OH	represents a combination of substituents corresponding to each row of Table B
Table 158	158- 1-158- 710	2-Chloro-5thlazolyl	A- 1	4- OH	represents a combination of substituants corresponding to each row of Table B
Table 159	159- 1-159- 710	6-Fluoro-3-pyridyl	A- 1	4- OH	represents a combination of substituents corresponding to each row of Table B

[Table 5-9]

Table 160

160- 1-160- 710

6-Bromo-3-pyridyi

A- 1

4- OH

represents a combination of substituents corresponding to each row of Table B

[Table 6-1]

Table A

	Compound No.	Ar	A	Y	R
Table 161	161- 1-161-710	6-Chloro-5-fiuoro- 3-pyridyl	A-1	4- OH	represents a combination of substituents corresponding to each row of Table B
Table 162	162- 1-162-710	2-Chioro-5pyrlmidinyl	A-1	4- OH	represents a combination of substltuents corresponding to each row of Table B
Table 163	163- 1-163-710	5-Chloropyrazin-2- yi	A-1	4- OH	represents a combination of substituents corresponding to each row of Table B
Table 164	164- 1-164-710	6-Chloropyrldazln- 3-yl	A-1	4- OH	represents a combination of substltuents corresponding to each row of Table B
Table 165	165- 1-165-710	2-Chioro-5- oxazolyl	A-1	4- 0H	represents a combination of substltuents corresponding to each row of Table B
Table 166	166- 1-166-710	6-trifluoromethyl-3- pyridyl	A-1	4- OH	represents a combination of substltuents corresponding to each row of Table B

[Table 6-2]

Table 167	167- 1-167-710	3-tetrahydrofuranyl	A-1	4- OH	represents a combination of substituents corresponding to each row of Table B
Table 168	168- 1-168-710	6-Chloro-3-pyridyl	A-1	5- OH	represents a combination of substituents corresponding to each row of Table B
Table 169	169- 1-169-710	2-Chloro-5thlazolyl	A-1	5- OH	represents a combination of substituents corresponding to each row of Table B
Table 170	170- 1-170-710	6-Fluoro-3-pyrldyl	A-1	5- OH	represents a combination of substituents corresponding to each row of Table B
Table 171	171- 1-171-710	6-Bromo-3-pyridyl	A-1	5- OH	represents a combination of substituents corresponding to each row of Table B
Table 172	172- 1-172-710	6-Chloro-5-fluoro- 3-pyrldyl	A-1	5- OH	represents a combination of substituents corresponding to each row of Table B
Table 173	173- 1-173-710	2-Chloro-5pyrimidinyl	A-1	5- OH	represents a combination of substituents corresponding to each row of Table B

[Table 6-3]

Table 174	174- 1-174-710	5-Chloropyrazin-2- yi	A-1	5- OH	represents a combination of substituents corresponding to each row of Table B
Table 175	175- 1-175-710	6-Chloropyridazln- 3-yl	A-1	5- OH	represents a combination of substituents corresponding to each row of Table B
Table	176-	2-Chloro-5-	A-1	5-	represents a combination of

176	1-176-710	oxazolyl		OH	substituents corresponding to each row of Table B
Table 177	177-1-77- 710	6-trlfluoromethyl-3pyrldyl	A-1	5- OH	represents a combination of substituents corresponding to each row of Table B
Table 178	178- 1-178-710	3-tetrahydrofuranyl	A-1	5- OH	represents a combination of substituents corresponding to each row of Table B
Table 179	179- 1-179-710	6-Chloro-3-pyrldyl	A-1	6- OH	represents a combination of substituents corresponding to each row of Table B
Table 180	180- 1-180-710	2-Chloro-5thlazolyl	A-1	6- OH	represents a combination of substituents corresponding to each row of Table B

[Table 6-4]

Table 181	181- 1-181-710	6-Fluoro-3-pyridyl	A-1	6- OH	represents a combination of substituents corresponding to each row of Table B
Table 182	182- 1-182-710	6-Bromo-3-pyridyi	A-1	6- OH	represents a combination of substituents corresponding to each row of Table B
Table 183	183- 1-183-710	6-Chloro-5-fluoro- 3-pyrldyl	A-1	6- OH	represents a combination of substituents corresponding to each row of Table B
Table 184	184- 1-184-710	2-Chioro-5pyrlmldlnyl	A-1	6- OH	represents a combination of substituents corresponding to each row of Table B
Table 185	185- 1-185-710	5-Chloropyrazin-2- yi	A-1	6- OH	represents a combination of substituents corresponding to each row of Table B

Table 186	186- 1-186-710	6-Chloropyridazin- 3-yl	A-1	6- OH	represents a combination of substituents corresponding to each row of Table B
Table 187	187- 1-187-710	2-Chloro-5oxazolyl	A-1	6- OH	represents a combination of substituents corresponding to each row of Table B

[Table 6-5]

Table 188	188- 1-188-710	6-trlffuoromethyl-3pyrldyl	A-1	6- OH	represents a combination of substituents corresponding to each row of Table B
Table 189	189- 1-189-710	3-tetrahydrofuranyl	A-1	6- OH	represents a combination of substituents corresponding to each row of Table B
Table 190	190- 1-190-710	6-Chloro-3-pyrldyl	A- 13	H	represents a combination of substituents corresponding to each row of Table B
Table 191	191- 1-191-710	2-Chloro-5- thlazolyl	A- 13	H	represents a combination of substituents corresponding to each row of Table B
Table 192	192- 1-192-710	6-Fluoro-3-pyrldyl	A- 13	H	represents a combination of substituents corresponding to each row of Table B

[Table 7-1]

Table A

	Compound No.	Ar	A	Y	R
Table 193	193- 1-193-710	6-Bromo-3-pyridyl	A- 13	H	represents a combination of substituents corresponding to each

					row of Table B
Table 194	194- 1-194-710	6-Chloro-5-fiuoro- 3-pyridyi	A- 13	H	represents a combination of substituents corresponding to each row of Table B
Table I95	195- 1-195-710	2-Chioro-5pyrlmîd inyl	A- 13	H	represents a combination of substituents corresponding to each row of Table B
Table 196	196- 1-196-710	5-Chloropyrazin-2- yi	A- 13	H	represents a combination of substituents corresponding to each row of Table B
Table 197	197- 1-197-710	6-Chloropyrldazln- 3-yi	A- 13	H	represents a combination of substituents corresponding to each row of Table B
Table 198	198- 1-198-710	2-Chloro-5- oxazolyl	A- 13	H	represents a combination of substituents corresponding to each row of Table B

[Table 7-2]

Table 199	199- 1-199-710	6-trlfiuoromethy1-3pyridyi	A- 13	H	represents a combination of substituents corresponding to each row of Table B
Table 200	200- 1-200-710	3-tetrahydrofuranyl	A- 13	H	represents a combination of substituents corresponding to each row of Table B
Table 201	201- 1-201-710	6-Chloro-3-pyridyl	A- 14	H	represents a combination of substituents corresponding to each row of Table B
Table 202	202- 1-202-710	2-Chloro-5thlazolyl	A- 14	H	represents a combination of substituents corresponding to each row of Table B
Table	203-	6-Fluoro-3-pyridyl	A-	H	represents a combination of substituents

203	1-203-710		14		corresponding to each row of Table B
Table 204	204- 1-204-710	6-Bromo-3-pyrldyl	A- 14	H	represents a combination of substituents corresponding to each row of Table B
Table 205	205- 1-205-710	6-Chloro-5-fiuoro- 3-pyridyl	A- 14	H	represents a combination of substituents corresponding to each row of Table B

[Table 7-3]

Table 206	206- 1-206-710	2-Chloro-5pyrimidinyl	A- 14	H	represents a combination of substituents corresponding to each row of Table B
Table 207	207- 1-207-710	5-Chloropyrazln-2- yi	A- 14	H	represents a combination of substituants corresponding to each row of Table B
Table 208	208- 1-208-710	6-Chloropyrldazln- 3-yl	A- 14	H	represents a combination of substituents corresponding to each row of Table B
Table 209	209- 1-209-710	2-Chloro-5oxazolyl	A- 14	H	represents a combination of substituents corresponding to each row of Table B
Table 210	210- 1-210-710	6-trlfluoromethyl-3pyridyl	A- 14	H	represents a combination of substituents corresponding to each row of Table B
Table 211	211- 1-211-710	3-tetrahydrofuranyl	A- 14	H	represents a combination of substituants corresponding to each row of Table B
Table 212	212- 1-212-710	6-Chloro-3-pyridyl	A- 15	H	represents a combination of substituents corresponding to each row of Table B

[Table 7-4]

Table 213	213- 1-213-710	2-Chloro-5thlazolyl	A- 15	H	represents a combination of substituents corresponding to each row of Table B
Table 214	214- 1-214-710	6-Fluoro-3-pyrldyl	A- 15	H	represents a combination of substituents corresponding to each row of Table B
Table 215	215- 1-215-710	6-Bromo-3-pyrldyl	A- 15	H	represents a combination of substituents corresponding to each row of Table B
Table 216	216- 1-216-710	6-Chloro-5-fluoro- 3-pyrldyl	A- 15	H	represents a combination of substituents corresponding to each row of Table B
Table 217	217- 1-217-710	2-Chloro-5pyrlmldinyl	A- 15	H	represents a combination of substituents corresponding to each row of Table B
Table 218	218- 1-218-710	5-Chloropyrazin-2- yi	A- 15	H	represents a combination of substituents corresponding to each row of Table B
Table 219	219- 1-219-710	6-Chloropyridazin- 3-yl	A- 15	H	represents a combination of substituents corresponding to each row of Table B

[Table 7-5]

Table 220	220- 1-220-710	2-Chloro-5oxazolyl	A- 15	H	represents a combination of substituents corresponding to each row of Table B
Table 221	221- 1-221-710	6-trifluoromethyl-3pyridyl	A- 15	H	represents a combination of substituents corresponding to each row of Table B
Table	222-	3-tetrahydrofuranyl	A-	H	represents a combination of

222	1-222-710		15		substituents corresponding to each row of Table B
Table 223	223- 1-223-710	6-Chloro-3-pyridyl	A- 16	H	represents a combination of substituents corresponding to each row of Table B
Table 224	224- 1-224-710	2-Chloro-5thlazolyl	A- 16	H	represents a combination of substituents corresponding to each row of Table B

fiable 8-1]

Table A

	Compound No.	Ar	A	Y	R
Table 225	225- 1-225-710	6-Fluoro-3-pyrldyl	A- 16	H	represents a combination of substituents corresponding to each row of Table B
Table 226	226- 1-226-710	6-Bromo-3-pyridyl	A- 16	H	represents a combination of substituents corresponding to each row of Table B
Table 227	227- 1-227-710	6-Chloro-5-fluoro- 3-pyrldyl	A- 16	H	represents a combination of substituents corresponding to each row of Table B
Table 228	228- 1-228-710	2-Chloro-5pyrimidinyl	A- 16	H	represents a combination of substituents corresponding to each row of Table B
Table 229	229- 1-229-710	5-Chloropyrazln-2- yi	A- 16	H	represents a combination of substituents corresponding to each row of Table B
Table 230	230- 1-230-710	6-Chloropyrldazln- 3-yl	A- 16	H	represents a combination of substituents corresponding to each row of Table B

(Table 8-2]

Table 231	231- 1-231-710	2-Chloro-5oxazolyl	A- 16	H	represents a combination of substituents corresponding to each row of Table B
Table 232	232- 1-232-710	6-trlfluoromethyl-3pyrldyl	A- 16	H	represents a combination of substituents corresponding to each row of Table B
Table 233	233- 1-233-710	3-tetrahydrofuranyl	A- 16	H	represents a combination of substituents corresponding to each row of Table B
Table 234	234- 1-234-710	6-Chloro-3-pyridyl	A-2	H	represents a combination of substituents corresponding to each row of Table B
Table 235	235- 1-235-710	6-Chloro-3-pyridyi	A-3	H	represents a combination of substituents corresponding to each row of Table B
Table 236	236- 1-236-710	6-Chloro-3-pyrldyl	A-4	H	represents a combination of substituents corresponding to each row of Table B
Table 237	237- 1-237-710	6-Chloro-3-pyrldyl	A-5	H	represents a combination of substituents corresponding to each row of Table B

[Table 8-3]

Table 238	238- 1-238-710	6-Chloro-3-pyridyl	A-6	H	represents a combination of substituents corresponding to each row of Table B
Table 239	239- 1-239-710	6-Chloro-3-pyridyl	A-7	H	represents a combination of substituents corresponding to each row of Table B

Table 240	240- 1-240-710	6-Chloro-3-pyrldyl	A-8	H	represents a combination of substituents corresponding to each row of Table B
Table 241	241- 1-241-710	6-Chloro-3-pyridyl	A-9	H	represents a combination of substituents corresponding to each row of Table B
Table 242	242- 1-242-710	6-Chloro-3-pyrldyl	A- 10	H	represents a combination of substituents corresponding to each row of Table B
Table 243	243- 1-243-710	6-Chloro-3-pyridyl	A- 11	H	represents a combination of substituents corresponding to each row of Table B
Table 244	244- 1-244-710	6-Chloro-3-pyrldyl	A- 12	H	represents a combination of substituents corresponding to each row of Table B

[Table 8-4]

Table 245	245- 1-245-710	6-Chloro-3-pyrldyl	A- 17	H	represents a combination of substituents corresponding to each row of Table B
Table 246	246- 1-246-710	6-Chloro-3-pyrldyl	A- 18	H	represents a combination of substituents corresponding to each row of Table B
Table 247	247- 1-247-710	6-Chloro-3-pyrldyl	A- 19	H	represents a combination of substituents corresponding to each row of Table B
Table 248	248- 1-248-710	6-Chloro-3-pyrldyl	A- 20	H	represents a combination of substituents corresponding to each row of Table B
Table 249	249- 1-249-710	6-Chloro-3-pyrldyl	A- 21	H	represents a combination of substituents corresponding to each

					row of Table B
Table 250	250- 1-250-710	6-Chloro-3-pyrldyl	A- 22	H	represents a combination of substituents corresponding to each row of Table B
Table 251	251- 1-251-710	6-Chloro-3-pyridyl	A- 23	H	represents a combination of substituents corresponding to each row of Table B

[Table 8-5]

Table 252	252- 1-252-710	6-Chioro-3-pyr1dyl	A- 24	H	represents a combination of substituents corresponding to each row of Table B
Table 253	253- 1-253-710	6-Chloro-3-pyr1dyl	A- 25	H	represents a combination of substituents corresponding to each row of Table B
Table 254	254- 1-254-710	6-Chloro-3-pyridyl	A- 26	H	represents a combination of substituents corresponding to each row of Table B
Table 255	255- 1-255-710	6-Chloro-3-pyridyl	A- 27	H	represents a combination of substituents corresponding to each row of Table B
Table 256	256- 1-256-710	6-Chloro-3-pyr1dyi	A- 28	H	represents a combination of substituents corresponding to each row of Table B

[Table 9-1]

Table A

	Compound No.	Ar	A	Y	R
Table	257-	6-Chioro-3-pyr1dyi	A-	H	represents a combination of substituants

257	1-257-710		29		corresponding to each row of Table B
Table 258	258- 1-258-710	6-Chloro-3-pyridyl	A- 30	H	represents a combination of substituents corresponding to each row of Table B
Table 259	259- 1-259-710	6-Chloro-3-pyridyl	A- 31	H	represents a combination of substituents corresponding to each row of Table B
Table 260	260- 1-260-710	6-Chloro-3-pyrldyl	A- 32	H	represents a combination of substituents corresponding to each row of Table B
Table 261	261- 1-261-710	6-Chloro-3-pyridyl	A- 33	H	represents a combination of substituents corresponding to each row of Table B
Table 262	262- 1-262-710	6-Chloro-3-pyrldyl	A- 34	H	represents a combination of substituents corresponding to each row of Table B

[Table 9-2]

Table 263	263- 1-263-710	6-Chloro-3-pyrldyl	A- 35	H	represents a combination of substituents corresponding to each row of Table B
Table 264	264- 1-264-710	6-Chloro-3-pyrldyl	A- 36	H	represents a combination of substituents corresponding to each row of Table B
Table 265	265- 1-265-710	6-Chloro-3-pyridyl	A- 37	H	represents a combination of substituents corresponding to each row of Table B
Table 266	266- 1-266-710	6-Chloro-3-pyridyl	A- 38	H	represents a combination of substituents corresponding to each row of Table B
Table	267-	6-Chioro-3-pyridyl	A-	H	represents a combination of

267	1-267-710		39		substituents corresponding to each row of Table B
Table 268	268- 1-268-710	6-Chloro-3-pyrldyl	A- 40	H	represents a combination of substituents corresponding to each row of Table B
Table 269	269-1-269- 710	6-Chloro-3-pyridyl	A-2	H	represents a combination of substituents corresponding to each row of Table B

[Table 9-3]

Table 270	270- 1-270-710	6-Chloro-3-pyrldyl	A-3	H	represents a combination of substituents corresponding to each row of Table B
Table 271	271- 1-271-710	6-Chloro-3-pyridyl	A-4	H	represents a combination of substituents corresponding to each row of Table B
Table 272	272- 1-272-710	6-Chloro-3-pyridyl	A-5	H	represents a combination of substituents corresponding to each row of Table B
Table 273	273- 1-273-710	6-Chloro-3-pyridyl	A-6	H	represents a combination of substituents corresponding to each row of Table B
Table 274	274- 1-274-710	6-Chloro-3-pyridyl	A-7	H	represents a combination of substituents corresponding to each row of Table B
Table 275	275- 1-275-710	6-Chloro-3-pyridyl	A-8	H	represents a combination of substituents corresponding to each row of Table B
Table 276	276- 1-276-710	6-Chloro-3-pyrldyl	A-9	H	represents a combination of substituents corresponding to each row of Table B

[Table 9-4]

Table 277	277- 1-277-710	6-Chloro-3-pyridyl	A- 10	H	represents a combination of substltuents corresponding to each row of Table B
Table 278	278- 1-278-710	6-Chloro-3-pyridyl	A- 11	H	represents a combination of substltuents corresponding to each row of Table B
Table 279	279- 1-279-710	6-Chloro-3-pyrldyl	A- 12	H	represents a combination of substltuents corresponding to each row of Table B
Table 280	280- 1-280-710	6-Chloro-3-pyridyl	A- 17	H	represents a combination of substltuents corresponding to each row of Table B
Table 281	281- 1-281-710	6-Chloro-3-pyrldyl	A- 18	H	represents a combination of substituents corresponding to each row of Table B
Table 282	282- 1-282-710	6-Chloro-3-pyrldyl	A- 19	H	represents a combination of substltuents corresponding to each row of Table B
Table 283	283- 1-283-710	6-Chloro-3-pyrldyl	A- 20	H	represents a combination of substltuents corresponding to each row of Table B

[Table 9-5]

Table 284	284- 1-284-710	6-Chloro-3-pyridyl	A- 21	H	represents a combination of substltuents corresponding to each row of Table B
Table 285	285- 1-285-710	6-Chloro-3-pyrldyl	A- 22	H	represents a combination of substltuents corresponding to each row of Table B

Table 286	286- 1-286-710	6-Chloro-3-pyrldyl	A- 23	H	represents a combination of substituents corresponding to each row of Table B
Table 287	287- 1-287-710	6-Chloro-3-pyrldyl	A- 24	H	represents a combination of substituents corresponding to each row of Table B
Table 288	288- 1-288-710	6-Chloro-3-pyrldyl	A- 25	H	represents a combination of substituents corresponding to each row of Table B

[Table 10-1]

Table A

	Compound No.	Ar	A	Y	R
Table 289	289- 1-289-710	6-Chloro-3-pyrldyl	A- 26	H	represents a combination of substituents corresponding to each row of Table B
Table 290	290- 1-290-710	6-Chloro-3-pyridyl	A- 27	H	represents a combination of substituents corresponding to each row of Table B
Table 291	291- 1-291-710	6-Chloro-3-pyridyl	A- 28	H	represents a combination of substituents corresponding to each row of Table B
Table 292	292- 1-292-710	6-Chloro-3-pyrldyl	A- 29	H	represents a combination of substituents corresponding to each row of Table B
Table 293	293- 1-293-710	6-Chloro-3-pyridyl	A- 30	H	represents a combination of substituents corresponding to each row of Table B
Table	294-	6-Chloro-3-pyridyl	A-	H	represents a combination of substituents

294

1-294-710

31

corresponding to each row of Table B

[Table 10-2]

Table 295	295- 1-295-710	6-Chloro-3-pyrldyl	A- 32	H	represents a combination of substituents corresponding to each row of Table B
Table 296	296- 1-296-710	6-Chloro-3-pyrldy!	A- 33	H	represents a combination of substituents corresponding to each row of Table B
Table 297	297- 1-297-710	6-Chloro-3-pyrldyl	A- 34	H	represents a combination of substituents corresponding to each row of Table B
Table 298	298- 1-298-710	6-Ch!oro-3-pyrldyl	A- 35	H	represents a combination of substituents corresponding to each row of Table B
Table 299	299- 1-299-710	6-Chloro-3-pyridyl	A- 36	H	represents a combination of substituents corresponding to each row of Table B
Table 300	300- 1-300-710	6-Chloro-3-pyrldyl	A- 37	H	represents a combination of substituents corresponding to each row of Table B
Table 301	301- 1-301-710	6-Chloro-3-pyrldyl	A- 38	H	represents a combination of substituents corresponding to each row of Table B

[Table 10-3]

Table 302	302- 1-302-710	6-Chloro-3-pyrldyl	A- 39	H	represents a combination of substituents corresponding to each row of Table B
Table	303-	6-Chloro-3-pyrldyl	A-	H	represents a combination of substituents

303	1-303-710		40		corresponding to each row of Table B
Table 304	304- 1-304-710	6-Chloro-3-pyrldyl	A-2	H	represents a combination of substituents corresponding to each row of Table B
Table 305	305- 1-305-710	6-Chloro-3-pyrldyl	A-3	H	represents a combination of substituents corresponding to each row of Table B
Table 306	306- 1-306-710	6-Chloro-3-pyridyl	A-4	H	represents a combination of substituents corresponding to each row of Table B
Table 307	307- 1-307-710	6-Chloro-3-pyridyl	A-5	H	represents a combination of substituents corresponding to each row of Table B
Table 308	308- 1-308-710	6-Chioro-3-pyridyl	A-6	H	represents a combination of substituents corresponding to each row of Table B

[Table 10-4]

Table 309	309- 1-309-710	6-Chloro-3-pyridyl	A-7	H	represents a combination of substituents corresponding to each row of Table B
Table 310	310- 1-310-710	6-Chioro-3-pyridyl	A-8	H	represents a combination of substituents corresponding to each row of Table B
Table 311	311- 1-311-710	6-Chloro-3-pyrldyl	A-9	H	represents a combination of substituents corresponding to each row of Table B
Table 312	312- 1-312-710	6-Chloro-3-pyridyl	A- 10	H	represents a combination of substituents corresponding to each row of Table B
Table	313-	6-Chloro-3-pyridyl	A-	H	represents a combination of

313	1-313-710		11		substituents corresponding to each row of Table B
Table 314	314- 1-314-710	6-Chloro-3-pyrldyl	A- 12	H	represents a combination of substituents corresponding to each row of Table B
Table 315	315- 1-315-710	6-Chloro-3-pyrldyl	A- 17	H	represents a combination of substituents corresponding to each row of Table B

[Table 10-5]

Table 316	316- 1-316-710	6-Chloro-3-pyrldyl	A- 18	H	represents a combination of substituents corresponding to each row of Table B
Table 317	317- 1-317-710	6-Chloro-3-pyridyl	A- 19	H	represents a combination of substituents corresponding to each row of Table B
Table 318	318- 1-318-710	6-Chloro-3-pyridyl	A- 20	H	represents a combination of substituents corresponding to each row of Table B
Table 319	319- 1-319-710	6-Chloro-3-pyridyl	A- 21	H	represents a combination of substituents corresponding to each row of Table B
Table 320	320- 1-320-710	6-Chloro-3-pyridyl	A- 22	H	represents a combination of substituents corresponding to each row of Table B

(Table 11-1]

Table A

Compou nd No

Ar

A

Y

R

Table 321	321- 1-321- 710	6-Chloro-3pyrldyl	A-23	H	represents a combination of substituents corresponding to each row of Table B
Table 322	322- 1-322- 710	6-Chloro-3pyridyl	A-24	H	represents a combination of substituents corresponding to each row of Table B
Table 323	323- 1-323- 710	6-Chioro-3pyrldyi	A-25	H	represents a combination of substituents corresponding to each row of Table B
Table 324	324- 1-324- 710	6-Chloro-3pyridyl	A-26	H	represents a combination of substituents corresponding to each row of Table B

[Table 11-2]

Tabie 325	325- 1-325-710	6-Chloro-3-pyrldyl	A-27	H	represents a combination of substituents corresponding to each row of Table B
Table 326	326- 1-326-710	6-Chloro-3-pyrldyl	A-28	H	represents a combination of substituents

					corresponding to each row of Table B
Table 327	327- 1-327-710	6-Chloro-3-pyridyl	A-29	H	represents a combination of substituents corresponding to each row of Table B
Table 328	328- 1-328-710	6-Chloro-3-pyrldyl	A-30	H	represents a combination of substituents corresponding to each row of Table B

[Table 11-3]

Table 329	329- 1-329-710	6-Chloro-3-pyrldyl	A-31	H	represents a combination of substituents corresponding to each row of Table B
Table 330	330- 1-330-710	6-Chioro-3-pyridyi	A-32	H	represents a combination of substituents corresponding to each row of Table B
Table 331	331- 1-331-710	6-Chloro-3-pyrldyi	A-33	H	represents a combination of substituents

					corresponding to each row of Table B
Table 332	332- 1-332-710	6-Chloro-3-pyrldyl	A-34	H	represents a combination of substituents corresponding to each row of Table B

[Table 11-4]

Table 333	333- 1-333-710	6-Chloro-3-pyridyl	A-35	H	represents a combination of substituents corresponding to each row of Table B
Table 334	334- 1-334-710	6-Chloro-3-pyridyl	A-36	H	represents a combination of substituents corresponding to each row of Table B
Table 335	335- 1-335-710	6-Chloro-3-pyrldyl	A-37	H	represents a combination of substituents corresponding to each row of Table B
Table 336	336- 1-336-710	6-Chloro-3-pyrldyl	A-38	H	represents a combination of substituents

corresponding to each row of Table B

[Table 11-5]

Table 337	337- 1-337-710	6-Chloro-3-pyridyl	A-39	H	represents a combination of substituents corresponding to each row of Table B
Table 338	338- 1-338-710	6-Chioro-3-pyridyl	A-40	H	represents a combination of substituents corresponding to each row of Table B
Table 339	339- 1-339-710	2-Chloro-5thlazolyl	A-2	H	represents a combination of substituents corresponding to each row of Table B
Table 340	340- 1-340-710	3- Trlfluoromethylphe nyl	A-3	H	represents a combination of substituents corresponding to each row of Table B

[Table 11-6]

Table 341

341- 1-341-710

2-Methylphenyl

A-4

H

represents a combination of

					substituents corresponding to each row of Table B
Table 342	342- 1-342-710	3-Methylphenyl	A-5	H	represents a combination of substituents corresponding to each row of Table B
Table 343	343- 1-343-710	4-Methylphenyl	A-6	H	represents a combination of substituents corresponding to each row of Table B
Table 344	344- 1-344-710	4- Trifluoromethylphe nyl	A-7	H	represents a combination of substituents corresponding to each row of Table B

[Table 11-η

Table 345	345- 1-345-710	2- Trifluoromethylphe nyl	A-8	H	represents a combination of substituents corresponding to each row of Table B
Table 346	346- 1-346-710	2-Methoxyphenyl	A-9	H	represents a combination of

					substituents corresponding to each row of Table B
Table 347	347- 1-347-710	3-Methoxyphenyl	A-10	H	represents a combination of substituents corresponding to each row of Table B
Table 348	348- 1-348-710	4-Methoxyphenyl	A-11	H	represents a combination of substituents corresponding to each row of Table B

[Table 11-8]

Table 349	349- 1-349-710	2-Cyanophenyl	A-12	H	represents a combination of substituents corresponding to each row of Table B
Table 350	350- 1-350-710	3-Cyanophenyl	A-17	H	represents a combination of substituents corresponding to each row of Table B
Table 351	351- 1-351-710	4-Cyanophenyl	A-18	H	represents a combination of

					substituents corresponding to each row of Table B
Table 352	352- 1-352-710	2-Nitrophenyl	A-19	H	represents a combination of substituents corresponding to each row of Table B

[Table 12-1]

Table A

	Compou nd No	Ar	A	Y	R
Table 353	353- 1-353- 710	3-Nitrophenyl	A- 20	H	represents a combination of substituents corresponding to each row of Table B
Table 354	354- 1-354- 710	4-Nitrophenyl	A- 21	H	represents a combination of substituents corresponding to each row of Table B
Table 355	355- 1-355- 710	3-Hydroxy-2pyridyl	A- 22	H	represents a combination of substituents corresponding to each row of Table B
Table 356	356- 1-356- 710	4-hydroxy-2-pyridyl	A- 23	H	represents a combination of substituents corresponding to each row of Table B

[Table 12-2]

Table 357	357- 1-357-710	5-hydroxy-2pyridyl	A-24	H	represents a combination of substituents corresponding to each row of Table B
Table 358	358- 1-358-710	6-hydroxy-2pyrldyl	A-25	H	represents a combination of substituents corresponding to each row of Table B
Table 359	359- 1-359-710	2-Hydroxy-3- pyrldyl	A-26	H	represents a combination of substituents corresponding to each row of Table B
Table 360	360- 1-360-710	5-Hydroxy-3pyrldyl	A-27	H	represents a combination of substituents corresponding to each row of Table B

[Table 12-3]

Table 361

361- 1-361-710

6-Hydroxy-3pyrldyl

A-28

H

represents a combination of substituents corresponding to each

					row of Table B
Table 362	362- 1-362-710	4-Hydroxy-3pyridyl	A-29	H	represents a combination of substituents corresponding to each row of Table B
Table 363	363- 1-363-710	2-Hydroxy-4pyrldyl	A-30	H	represents a combination of substituents corresponding to each row of Table B
Table 364	364- 1-364-710	3-Hydroxy-4pyrldyl	A-31	H	represents a combination of substituents corresponding to each row of Table B

[Table 12-4]

Table 365	365- 1-365-710	3-Chloro-2-pyridyl	A-32	H	represents a combination of substituents corresponding to each row of Table B
Table 366	366- 1-366-710	4-Chloro-2-pyrldyl	A-33	H	represents a combination of substituents corresponding to each

					row of Table B
Table 367	367- 1-367-710	5-Chloro-2-pyridyl	A-34	H	represents a combination of substituents corresponding to each row of Table B
Table 366	368- 1-368-710	6-Chloro-2-pyridyl	A-35	H	represents a combination of substltuents corresponding to each row of Table B

[Table 12-5]

Table 369	369- 1-369-710	2-Chloro-3-pyrldyl	A-36	H	represents a combination of substituents corresponding to each row of Table B
Table 370	370- 1-370-710	5-Chloro-3-pyridyl	A-37	H	represents a combination of substituents corresponding to each row of Table B
Table 371	371- 1-371-710	6-Chloro-3-pyridyl	A-38	H	represents a combination of substituents corresponding to each

					row of Table B
Table 372	372- 1-372-710	4-Chloro-3-pyrldyl	A-39	H	represents a combination of substituents corresponding to each row of Table B

[Table 12-6]

Table 373	373- 1-373-710	2-Chloro-4-pyridyl	A-40	H	represents a combination of substituents corresponding to each row of Table B
Table 374	374- 1-374-710	3-Chloro-4-pyrldyl	A-2	H	represents a combination of substituents corresponding to each row of Table B
Table 375	375- 1-375-710	3-bromo-2-pyrldyl	A-3	H	represents a combination of substituents corresponding to each row of Table B
Table 376	376- 1-376-710	4-bromo-2-pyridyi	A-4	H	represents a combination of substituents corresponding to each

row of Table B

[Table 12-η

Table 377	377- 1-377-710	5-bromo-2-pyridyi	A-5	H	represents a combination of substituents corresponding to each row of Table B
Table 378	378- 1-378-710	6-bromo-2-pyrldyl	A-6	H	represents a combination of substituents corresponding to each row of Table B
Table 379	379- 1-379-710	2-bromo-3-pyridyi	A-7	H	represents a combination of substituents corresponding to each row of Table B
Table 380	380- 1-380-710	5-bromo-3-pyridyl	A-8	H	represents a combination of substituents corresponding to each row of Table B

[Table 12-81

Table 381

381- 1-381-710

6-bromo-3-pyrldyl

A-9

H

represents a combination of substituents

					corresponding to each row of Table B
Table 382	382- 1-382-710	4-bromo-3-pyridyl	A-10	H	represents a combination of substituents corresponding to each row of Table B
Table 383	383- 1-383-710	2-bromo-4-pyrldyl	A-11	H	represents a combination of substituents corresponding to each row of Table B
Table 384	384- 1-384-710	3-bromo-4-pyrldyl	A-12	H	represents a combination of substituents corresponding to each row of Table B

[Table 13-1]

Table A

	Compound No	Ar	A	Y	R
Table 385	385- 1-385-710	3-Fluoro-2-pyridyl	A-17	H	represents a combination of substituents corresponding to each row of Table B

100

Table 386	386- 1-386-710	4-Fluoro-2-pyrldyl	A-18	H	represents a combination of substituents corresponding to each row of Table B
Table 387	387- 1-387-710	5-Fluoro-2-pyrldyl	A-19	H	represents a combination of substituents corresponding to each row of Table B

[Table 13-2]

Table 388	388- 1-388-710	6-Fluoro-2-pyrldyl	A-20	H	represents a combination of substituents corresponding to each row of Table B
Table 389	389- 1-389-710	2-Fluoro-3-pyridyl	A-21	H	represents a combination of substituents corresponding to each row of Table B
Table 390	390- 1-390-710	5-Fluoro-3-pyrldyl	A-22	H	represents a combination of substituents corresponding to

101

					each row of Table B
Table 391	391- 1-391-710	6-Fluoro-3-pyridyl	A-23	H	represents a combination of substituents corresponding to each row of Table B

[Table 13-3]

Table 392	392- 1-392-710	4-Fluoro-3-pyrldyl	A-24	H	represents a combination of substituents corresponding to each row of Table B
Table 393	393- 1-393-710	2-Fluoro-4-pyrldyl	A-25	H	represents a combination of substituents corresponding to each row of Table B
Table 394	394- 1-394-710	3-Fluoro-4-pyridyl	A-26	H	represents a combination of substituents corresponding to each row of Table B
Table 395	395- 1-395-710	6-Fluoro-3-pyridyl	A-27	H	represents a combination of substituents corresponding to

102

each row of Table B

[Table 13-4]

Table 396	396- 1-396-710	3-lodo-2-pyrldyl	A-28	H	represents a combination of substituents corresponding to each row of Table B
Table 397	397- 1-397-710	4-iodo-2-pyridyl	A-29	H	represents a combination of substituents corresponding to each row of Table B
Table 398	398- 1-398-710	5-lodo-2-pyrldyl	A-30	H	represents a combination of substituents corresponding to each row of Table B
Table 399	399- 1-399-710	6-lodo-2-pyrldyl	A-31	H	represents a combination of substituents corresponding to each row of Table B

[Table 13-5]

Table 400

400- 1-400-710

2-lodo-3-pyridyl

A-32

H

represents a combination of substituents

103

					corresponding to each row of Table B
Table 401	401- 1-401-710	5-lodo-3-pyrldyl	A-33	H	represents a combination of substltuents corresponding to each row of Table B
Table 402	402- 1-402-710	6-lodo-3-pyrldyl	A-34	H	represents a combination of substituents corresponding to each row of Table B
Table 403	403- 1-403-710	4-iodo-3-pyridyl	A-35	H	represents a combination of substituents corresponding to each row of Table B

[Table 13-6]

Table 404	404- 1-404-710	2-iodo-4-pyridyl	A-36	H	represents a combination of substituents corresponding to each row of Table B
Table 405	405- 1-405-710	3-lodo-4-pyrldyl	A-37	H	represents a combination of substituents

104

					corresponding to each row of Table B
Table 406	406- 1-406-710	6-lodo-3-pyridyl	A-38	H	represents a combination of substituents corresponding to each row of Table B
Table 407	407- 1-407-710	6-iodo-3-pyridyl	A-39	H	represents a combination of substituents corresponding to each row of Table B

[Table 13-7]

Table 408	408- 1-408-710	2tetrahydrofuranyl	A-40	H	represents a combination of substituents corresponding to each row of Table B
Table 409	409- 1-409-710	3tetrahydrofuranyl	A-2	H	represents a combination of substituents corresponding to each row of Table B
Table 410	410- 1-410-710	5-Chloro-2thiazolyl	A-3	H	represents a combination of substituents

105

					corresponding to each row of Table B
Table 411	411- 1-411-710	6-Fluoro-3-pyrldyl	A-4	H	represents a combination of substituents corresponding to each row of Table B

[Table 13-8]

Table 412	412- 1-412-710	6-Bromo-3-pyridyl	A-5	H	represents a combination of substituents corresponding to each row of Table B
Table 413	413- 1-413-710	6-Chloro-5-Fluoro- 3-pyridyl	A-6	H	represents a combination of substituents corresponding to each row of Table B
Table 414	414- 1-414-710	3,5- Dimethylphenyl	A-7	H	represents a combination of substituents corresponding to each row of Table B
Table 415	415- 1-415-710	2,3- Dimethylphenyl	A-8	H	represents a combination of substituents

106

corresponding to each row of Table B

[Table 13-9]

Table 416

416- 1-416-710

2,4- Dlmethyophenyl

A-9

H

represents a combination of substituents corresponding to each row of Table B

[Table 14-1]

Table A

	Compou nd No	Ar	A	Y	R
Table 417	417- 1-417- 710	Phenyl	A- 10	H	represents a combination of substituents corresponding to each row of Table B
Table 418	418- 1-418- 710	cyclopentyl	A- 11	H	represents a combination of substituents corresponding to each row of Table B
Table 419	419- 1-419- 710	cyclohexyl	A- 12	H	represents a combination of substituents corresponding to each row of Table B
Table 420	420- 1-420- 710	3- methylcyclohexy 1	A- 17	H	represents a combination of substituents corresponding to each row of Table B

107 [Table 14-2]

Table 421	421-1-421- 710	cyclobutyl	A-18	H	represents a combination of substituents corresponding to each row of Table B
Table 422	422-1 -422-710	2-oxetanyl	A-19	H	represents a combination of substituents corresponding to each row of Table B
Table 423	423-1-423- 710	3-oxetanyl	A-20	H	represents a combination of substituents corresponding to each row of Table B
Table 424	424-1-424- 710	2-thietanyi	A-21	H	represents a combination of substituents corresponding to each row of Table B

[Table 14-3]

Table 425

425-1-425- 710

3-thietanyl

A-22

H

represents a combination of substituents corresponding to each

108

					row of Table B
Table 426	426-1-426- 710	2-azetidinyl	A-23	H	represents a combination of substituents corresponding to each row of Table B
Table 427	427-1-427- 710	3-azetidinyl	A-24	H	represents a combination of substituants corresponding to each row of Table B
Table 428	428-1-428- 710	6-iodo-3-pyrldyl	A-25	H	represents a combination of substituents corresponding to each row of Table B

[Table 14-4]

Table 429	429-1-429- 710	6-iodo-3-pyridyl	A-26	H	represents a combination of substituents corresponding to each row of Table B
Table 430	430-1-430- 710	2tetrahydrofuranyl	A-27	H	represents a combination of substituants corresponding to each

109

					row of Table B
Table 431	431-1-431- 710	2-Chloro-3- pyrldyl	A-28	H	represents a combination of substituents corresponding to each row of Table B
Table 432	432-1-432- 710	5-Ch!oro-3pyridy!	A-29	H	represents a combination of substituents corresponding to each row of Table B

[Table 14-5]

Table 433	433-1-433- 710	6-Chloro-3- pyrldyl	A-30	H	represents a combination of substituents corresponding to each row of Table B
Table 434	434-1-434- 710	4-Chloro-3pyridyi	A-31	H	represents a combination of substituents corresponding to each row of Table B
Table 435	435-1-435- 710	2-Chloro-4pyrldyl	A-32	H	represents a combination of substituents corresponding to each

110

					row of Table B
Table 436	436-1-436- 710	3-Chloro-4- pyridyl	A-33	H	represents a combination of substituents corresponding to each row of Table B

[Table 14-6]

Table 437	437-1-437- 710	3-bromo-2- pyrldyl	A-34	H	represents a combination of substituents corresponding to each row of Table B
Table 438	438-1-438- 710	4-bromo-2- pyrldyl	A-35	H	represents a combination of substituents corresponding to each row of Table B
Table 439	439-1-439- 710	2-Fluoro-4- pyrldyl	A-36	H	represents a combination of substituents corresponding to each row of Table B
Table 440	440-1-440- 710	3-Fluoro-4- pyridyl	A-37	H	represents a combination of substituents corresponding to each

111

row of Table B

[Table 147]

Table 441	441-1-441- 710	6-Fluoro-3- pyridyi	A-38	H	represents a combination of substituents corresponding to each row of Table B
Table 442	442-1-442- 710	3-iodo-2-pyridyl	A-39	H	represents a combination of substituents corresponding to each row of Table B
Table 443	443-1-443- 710	6-Fluoro-3- pyridyl	A-40	H	represents a combination of substituents corresponding to each row of Table B
Table 444	444-1-444- 710	2-Chloro-5- thiazolyl	A-38	H	represents a combination of substituents corresponding to each row of Table B

[Table 15-1]

Table A

Compound No.

Ar

A

Y

R

112

Table 445	445-1-445- 710	6-Chloro-3pyridyl	A-1	3-CH3	represents a combination of substituents corresponding to each row of Table B
Table 446	446-1-446- 710	2-Chloro-5thiazolyl	A-1	3-CH3	represents a combination of substituents corresponding to each row of Table B
Table 447	447-1-447- 710	6-Fluoro-3pyrldyl	A-1	3-CH3	represents a combination of substituents corresponding to each row of Table B

[Table 15-2]

Table 448	448-1-448- 710	6-Bromo-3pyrldyl	A-1	3-CH3	represents a combination of substituents corresponding to each row of Table B
Table 449	449-1-449- 710	6-Chloro-5fiuoro-3-pyridyl	A-1	3-CH3	represents a combination of substituents corresponding to each

113

					row of Table B
Table 450	450-1-450- 710	2-Chioro-5pyrlmldlnyl	A-1	3-CH3	represents a combination of substituents corresponding to each row of Table B
Table 451	451-1-451- 710	5-Chloropyrazin- 2-yl	A-1	3-CH3	represents a combination of substituents corresponding to each row of Table B

[Table 15-3]

Table 452	452-1-452- 710	6- Chloropyrldazin- 3-yl	A-1	3-CH3	represents a combination of substituents corresponding to each row of Table B
Table 453	453-1-453- 710	2-Chloro-5- oxazolyl	A-1	3-CH3	represents a combination of substituants corresponding to each row of Table B
Table 454	454-1-454- 710	6-trifluoromethyl- 3-pyridyl	A-1	3-CH3	represents a combination of substituents corresponding to each

114

					row of Table B
Table 455	455-1-455- 710	3tetrahydrofuranyl	A-1	3-CH3	represents a combination of substltuents corresponding to each row of Table B

[Table 15-4]

Table 456	456-1-456- 710	6-Chloro-3- pyridyl	A-1	4-CH3	represents a combination of substltuents corresponding to each row of Table B
Table 457	457-1-457- 710	2-Chloro-5- thiazolyl	A-1	4-CH3	represents a combination of substltuents corresponding to each row of Table B
Table 458	458-1-458- 710	6-Fluoro-3pyridyl	A-1	4-CH3	represents a combination of substltuents corresponding to each row of Table B
Table 459	459-1-459- 710	6-Bromo-3pyrldyl	A-1	4-CH3	represents a combination of substituents corresponding to each

115

					row of Table B
[Table 15-5]
Table 460	460-1-460- 710	6-Chloro-5- Fluoro-3-pyridyl	A-1	4-CH3	represents a combination of substituents corresponding to each row of Table B
Table 461	461-1-461- 710	2-Chloro-5pyrimid inyl	A-1	4-CH3	represents a combination of substituents corresponding to each row of Table B
Table 462	462-1-462- 710	5-Chloropyrazin- 2-yl	A-1	4-CH3	represents a combination of substituents corresponding to each row of Table B
Table 463	463-1-463- 710	6- Chloropyridazin- 3-yl	A-1	4-CH3	represents a combination of substituents corresponding to each row of Table B
[Table 15-6]
Table 464	464-1-464- 710	2-Chloro-5oxazolyl	A-1	4-CH3	represents a combination of substituents

116

					corresponding to each row of Table B
Table 465	465-1-465- 710	6-trlfluoromethyl- 3-pyridyl	A-1	4-CH3	represents a combination of substituents corresponding to each row of Table B
Table 466	466-1-466- 710	3tetrahydrofuranyl	A-1	4-CH3	represents a combination of substituents corresponding to each row of Table B
Table 467	467-1-467- 710	6-Chloro-3pyrldyl	A-1	5-CH3	represents a combination of substituents corresponding to each row of Table B

[Table 15-η

Table 468	468-1-468- 710	2-Chioro-5thiazolyl	A-1	5-CH3	represents a combination of substituents corresponding to each row of Table B
Table 469	469-1-469- 710	6-Fluoro-3pyrldyl	A-1	5-CH3	represents a combination of substituents

117

					corresponding to each row of Table B
Table 470	470-1-470- 710	6-Bromo-3pyrldyl	A-1	5-CH3	represents a combination of substituents corresponding to each row of Table B
Table 471	471-1-471- 710	6-Chloro-5fluoro-3-pyrldyl	A-1	5-CH3	represents a combination of substituents corresponding to each row of Table B

[Table 15-8]

Table 472	472-1-472- 710	2-Chloro-5pyrimidinyl	A-1	5-CH3	represents a combination of substituents corresponding to each row of Table B
Table 473	473-1-473- 710	5-Chloropyrazln- 2-yl	A-1	5-CH3	represents a combination of substituents corresponding to each row of Table B
Table 474	474-1-474- 710	6- Chioropyrldazin- 3-yl	A-1	5-CH3	represents a combination of substituents

118

					corresponding to each row of Table B
Table 475	475-1-475- 710	2-Chloro-5oxazolyl	A-1	5-CH3	represents a combination of substltuents corresponding to each row of Table B

[Table 15-9]

Table 476

476-1-476- 710

6-trifluoromethyl- 3-pyridyl

A-1

5-CH3

represents a combination of substltuents corresponding to each row of Table B

[Table 16-1]

Table A

	Compound No.	Ar	A	Y	R
Table 477	477-1-477- 710	3tetrahydrofuranyl	A-1	5-CH3	represents a combination of substltuents corresponding to each row of Table B
Table 478	478-1-478- 710	6-Chloro-3pyridyl	A-1	6-CH3	represents a combination of substltuents

119

					corresponding to each row of Table B
Table 479	479-1-479- 710	2-Chloro-5thiazolyl	A-1	6-CH3	represents a combination of substituents corresponding to each row of Table B

[Table 16-2]

Table 480	480-1-480- 710	6-Fluoro-3pyridyl	A-1	6-CH3	represents a combination of substituents corresponding to each row of Table B
Table 481	481-1-481- 710	6-Bromo-3- pyridyl	A-1	6-CH3	represents a combination of substituents corresponding to each row of Table B
Table 482	482-1-482- 710	6-Chloro-5fiuoro-3-pyrldyi	A-1	6-CH3	represents a combination of substituents corresponding to each row of Table B
Table 483	483-1-483- 710	2-Chloro-5pyrlmldinyl	A-1	6-CH3	represents a combination of

120

substituants corresponding to each row of Table B

[Table 16-3]

Table 484	484-1-484- 710	5-Chloropyrazln- 2-yl	A-1	6-CH3	represents a combination of substituents corresponding to each row of Table B
Table 485	485-1-485- 710	6- Chloropyridazln- 3-yl	A-1	6-CH3	represents a combination of substituents corresponding to each row of Table B
Table 486	486-1-486- 710	2-Chloro-5oxazolyl	A-1	6-CH3	represents a combination of substituents corresponding to each row of Table B
Table 487	487-1-487- 710	6-trifluoromethyi- 3-pyridyl	A-1	6-CH3	represents a combination of substituents corresponding to each row of Table B

[Table 16-4]

Table

488-1-488-

3-

A-1

6-CH3

represents a

121

488	710	tetrahydrofuranyl			combination of substituents corresponding to each row of Table B
Table 489	489-1-489- 710	6-Chloro-3pyrldyl	A-1	3- NO2	represents a combination of substituents corresponding to each row of Table B
Table 490	490-1-490- 710	2-Chloro-5thlazolyi	A-1	3- NO2	represents a combination of substituents corresponding to each row of Table B
Table 491	491-1-491- 710	6-Fluoro-3pyrldyl	A-1	3- NO2	represents a combination of substituents corresponding to each row of Table B

[Table 16-5]

Table 492	492-1-492- 710	6-Bromo-3pyridyl	A-1	3- NO2	represents a combination of substituents corresponding to each row of Table B
Table	493-1-493-	6-Chloro-5-	A-1	3-	represents a

122

493	710	Fluoro-3-pyridyl		NO2	combination of substituents corresponding to each row of Table B
Table 494	494-1-494- 710	2-Chloro-5- pyrimidinyi	A-1	3- NO2	represents a combination of substituents corresponding to each row of Table B
Table 495	495-1-495- 710	5-Chloropyrazln- 2-yl	A-1	3- NO2	represents a combination of substituents corresponding to each row of Table B

[Table 16-6]

Table 496	496-1-496- 710	6- Chloropyridazin- 3-yl	A-1	3- NO2	represents a combination of substituents corresponding to each row of Table B
Table 497	497-1-497- 710	2-Chloro-5oxazolyl	A-1	3- NO2	represents a combination of substituents corresponding to each row of Table B
Table	498-1-498-	6-trifluoromethyl·	A-1	3-	represents a

123

498	710	3-pyridyl		NO2	combination of substituents corresponding to each row of Table B
Table 499	499-1-499- 710	3tetrahydrofuranyi	A-1	3- NO2	represents a combination of substituents corresponding to each row of Table B

[Table 16-η

Table 500	500-1-500- 710	6-Chloro-3pyrldyl	A-1	4- NO2	represents a combination of substituants corresponding to each row of Table B
Table 501	501-1-501- 710	2-Chioro-5thlazolyl	A-1	4- NO2	represents a combination of substituents corresponding to each row of Table B
Table 502	502-1-502- 710	6-Fluoro-3- pyridyi	A-1	4- NO2	represents a combination of substituents corresponding to each row of Table B
Table	503-1-503-	6-Bromo-3-	A-1	4-	represents a

124

503

710

pyridyl

NO2

combination of substituents corresponding to each row of Table B

[Table 16-8]

Table 504	504-1-504- 710	6-Chloro-5fluoro-3-pyridyl	A-1	4- NO2	represents a combination of substituents corresponding to each row of Table B
Table 505	505-1-505- 710	2-Chloro-5pyrimidinyl	A-1	4- NO2	represents a combination of substituents corresponding to each row of Table B
Table 506	506-1-506- 710	5-Chloropyrazin- 2-yl	A-1	4- NO2	represents a combination of substituents corresponding to each row of Table B
Table 507	507-1-507- 710	6- Chloropyrldazin- 3-yl	A-1	4- NO2	represents a combination of substituents corresponding to each row of Table B

[Table 16-9]

125

Table 508

508-1-508- 710

2-Chloro-5- oxazolyl

A-1

4- NO2

represents a combination of substituents corresponding to each row of Table B

[Table 17-1]

Table A

	Compound No.	Ar	A	Y	R
Table 509	509-1-509- 710	6-tri(luoromethyl- 3-pyridyl	A-1	4- NO2	represents a combination of substituents corresponding to each row of Table B
Table 510	510-1-510- 710	3tetrahydrofuranyl	A-1	4- NO2	represents a combination of substituents corresponding to each row of Table B
Table 511	511-1-511- 710	6-Chloro-3pyrldyl	A-1	5- NO2	represents a combination of substituents corresponding to each row of Table B

126 [Table 17-2]

Table 512	512-1-512- 710	2-Chloro-5- thlazolyl	A-1	5- NO2	represents a combination of substituents corresponding to each row of Table B
Table 513	513-1-513- 710	6-Fluoro-3pyridyl	A-1	5- NO2	represents a combination of substituents corresponding to each row of Table B
Table 514	514-1-514- 710	6-Bromo-3pyrldyl	A-1	5- NO2	represents a combination of substituents corresponding to each row of Table B
Table 515	515-1-515- 710	6-Chloro-5f luoro-3-pyri dyl	A-1	5- NO2	represents a combination of substituents corresponding to each row of Table B

[Table 17-3]

Table 516

516-1-516- 710

2-Chloro-5pyrimldinyl

A-1

5- NO2

represents a combination of substituents corresponding to each

127

					row of Table B
Table 517	517-1-517- 710	5-Chloropyrazin- 2-yl	A-1	5- NO2	represents a combination of substituents corresponding to each row of Table B
Table 518	518-1-518- 710	6- Chloropyridazln- 3-yl	A-1	5- NO2	represents a combination of substituents corresponding to each row of Table B
Table 519	519-1-519- 710	2-Chloro-5oxazolyl	A-1	5- NO2	represents a combination of substituents corresponding to each row of Table B

(Table 17-41

Table 520	520-1-520- 710	6-trlfluoromethyl- 3-pyridyl	A-1	5- NO2	represents a combination of substituents corresponding to each row of Table B
Table 521	521-1-521- 710	3tetrahydrofuranyl	A-1	5- NO2	represents a combination of substituents corresponding to each

128

					row of Table B
Table 522	522-1-522- 710	6-Chloro-3pyridyl	A-1	6- NO2	represents a combination of substituents corresponding to each row of Table B
Table 523	523-1-523- 710	2-Chloro-5- thlazolyl	A-1	6- NO2	represents a combination of substituents corresponding to each row of Table B

[Table 17-5]

Table 524	524-1-524- 710	6-Fluoro-3- pyridyi	A-1	6- NO2	represents a combination of substituents corresponding to each row of Table B
Table 525	525-1-525- 710	6-Bromo-3- pyrldyl	A-1	6- NO2	represents a combination of substituents corresponding to each row of Table B
Table 526	526-1-526- 710	6-Chloro-5Fluoro-3-pyridyl	A-1	6- NO2	represents a combination of substituents corresponding to each

129

					row of Table B
Table 527	527-1-527- 710	2-Chloro-5- pyrlmldinyl	A-1	6- NO2	represents a combination of substituents corresponding to each row of Table B

[Table 17-6]

Table 528	528-1-528- 710	5-Chloropyrazin- 2-yl	A-1	6- NO2	represents a combination of substituents corresponding to each row of Table B
Table 529	529-1-529- 710	6- Chloropyridazln- 3-yi	A-1	6- NO2	represents a combination of substituents corresponding to each row of Table B
Table 530	530-1-530- 710	2-Chloro-5oxazolyl	A-1	6- NO2	represents a combination of substituents corresponding to each row of Table B
Table 531	531-1-531- 710	6-trlfluoromethyl- 3-pyrldyl	A-1	6- NO2	represents a combination of substituents corresponding to each

130

row of Table B

[Table 17-η

Table 532	532-1-532- 710	3- tetrahydrofuranyl	A-1	6- NO2	represents a combination of substituents corresponding to each row of Table B
Table 533	533-1-533- 710	6-Chloro-3pyrldyl	A-1	3- OCH3	represents a combination of substituents corresponding to each row of Table B
Table 534	534-1-534- 710	2-Chloro-5thiazolyl	A-1	3- OCH3	represents a combination of substituents corresponding to each row of Table B
Table 535	535-1-535- 710	6-Fluoro-3- pyridyi	A-1	3- OCH3	represents a combination of substituents corresponding to each row of Table B

[Table 17-8]

Table 536

536-1-536- 710

6-Bromo-3- pyrldyl

A-1

3- OCH3

represents a combination of substituents

131

					corresponding to each row of Table B
Table 537	537-1-537- 710	6-Chloro-5fluoro-3-pyridyl	A-1	3- OCH3	represents a combination of substltuents corresponding to each row of Table B
Table 538	538-1-538- 710	2-Chloro-5pyrimidlnyi	A-1	3- OCH3	represents a combination of substituents corresponding to each row of Table B
Table 539	539-1-539- 710	5-Chloropyrazln- 2-yl	A-1	3- OCH3	represents a combination of substituents corresponding to each row of Table B

[Table 17-9]

Table 540

540-1-540- 710

6- Chloropyrldazln- 3-yl

A-1

3- OCH3

represents a combination of substltuents corresponding to each row of Table B

132 [Table 18-1]

Table A

	Compound No.	Ar	A	Y	R
Table 541	541-1-541- 710	2-Chloro-5oxazolyl	A-1	3- OCH3	represents a combination of substituents corresponding to each row of Table B
Table 542	542-1-542- 710	6-trlfluoromethyl- 3-pyrldyl	A-1	3- OCH3	represents a combination of substituents corresponding to each row of Table B
Table 543	543-1-543- 710	3tetrahydrofuranyl	A-1	3- OCH3	represents a combination of substltuents corresponding to each row of Table B

[Table 18-2]

Table 544

544-1-544- 710

6-Chloro-3- pyridyl

A-1

4- OCH3

represents a combination of substituents corresponding to each row of Table B

133

Table 545	545-1-545- 710	2-Chloro-5thlazolyl	A-1	4- OCH3	represents a combination of substituents corresponding to each row of Table B
Table 546	546-1-546- 710	6-Fluoro-3- pyridyi	A-1	4- OCH3	represents a combination of substituents corresponding to each row of Table B
Table 547	547-1-547- 710	6-Bromo-3- pyrldyl	A-1	4- OCH3	represents a combination of substituents corresponding to each row of Table B

[Table 18-3]

Table 548	548-1-548- 710	6-Chloro-5Fluoro-3-pyridyl	A-1	4- OCH3	represents a combination of substituents corresponding to each row of Table B
Table 549	549-1-549- 710	2-Chloro-5pyrimidinyi	A-1	4- OCH3	represents a combination of substituents corresponding to each row of Table B

134

Table 550	550-1-550- 710	5-Chloropyrazln- 2-yl	A-1	4- OCH3	represents a combination of substituents corresponding to each row of Table B
Table 551	551-1-551- 710	6- Chloropyrldazin- 3-yl	A-1	4- OCH3	represents a combination of substituents corresponding to each row of Table B

[Table 18-4]

Table 552	552-1-552- 710	2-Chloro-5oxazolyl	A-1	4- OCH3	represents a combination of substituents corresponding to each row of Table B
Table 553	553-1-553- 710	6-trlfluoromethyl- 3-pyridyl	A-1	4- OCH3	represents a combination of substituents corresponding to each row of Table B
Table 554	554-1-554- 710	3tetrahydrofuranyi	A-1	4- OCH3	represents a combination of substituents corresponding to each row of Table B

135

Table 555

555-1-555- 710

6-Chloro-3- pyrldyl

A-1

5- OCH3

represents a combination of substituents corresponding to each row of Table B

[Table 18-5]

Table 556	556-1-556- 710	2-Chioro-5thlazoiyl	A-1	5- OCH3	represents a combination of substituents corresponding to each row of Table B
Table 557	557-1-557- 710	6-Fluoro-3pyridyl	A-1	5- OCH3	represents a combination of substituents corresponding to each row of Table B
Table 558	558-1-558- 710	6-Bromo-3pyridyl	A-1	5- OCH3	represents a combination of substituents corresponding to each row of Table B
Table 559	559-1-559- 710	6-Chloro-5fiuoro-3-pyridyl	A-1	5- OCH3	represents a combination of substituents corresponding to each row of Table B

[Table 18-6]

136

Table 560	560-1-560- 710	2-Chloro-5pyrimidinyl	A-1	5- OCH3	represents a combination of substituents corresponding to each row of Table B
Table 561	561-1-561- 710	5-Chloropyrazln- 2-yl	A-1	5- OCH3	represents a combination of substituents corresponding to each row of Table B
Table 562	562-1-562- 710	6- Chloropyridazin- 3-yl	A-1	5- OCH3	represents a combination of substituents corresponding to each row of Table B
Table 563	563-1-563- 710	2-Chloro-5oxazolyl	A-1	5- OCH3	represents a combination of substituents corresponding to each row of Table B

[Table 18-η

Table 564

564-1-564- 710

6-trifluoromethyl- 3-pyridyl

A-1

5- OCH3

represents a combination of substituents corresponding to each row of Table B

137

Table 565	565-1-565- 710	3- tetrahydrofuranyi	A-1	5- OCH3	represents a combination of substituents corresponding to each row of Table B
Table 566	566-1-566- 710	6-Chioro-3pyrldyl	A-1	6- OCH3	represents a combination of substituents corresponding to each row of Table B
Tabie 567	567-1-567- 710	2-Chloro-5- thlazolyi	A-1	6- OCH3	represents a combination of substituents corresponding to each row of Table B

[Tabie 18-8]

Tabie 568	568-1-568- 710	6-Fiuoro-3- pyrldyi	A-1	6- OCH3	represents a combination of substituents corresponding to each row of Table B
Table 569	569-1-569- 710	6-Bromo-3pyrldyi	A-1	6- OCH3	represents a combination of substituents corresponding to each row of Table B

138

Table 570	570-1-570- 710	6-Chloro-5- Fluoro-3-pyrldyl	A-1	6- OCH3	represents a combination of substituents corresponding to each row of Table B
Table 571	571-1-571- 710	2-Chloro-5pyrimidinyi	A-1	6- OCH3	represents a combination of substituents corresponding to each row of Table B

[Table 18-9]

Table 572

572-1-572- 710

5-Chloropyrazln- 2-yl

A-1

6- OCH3

represents a combination of substituents corresponding to each row of Table B

[Table 19-1]

Table A

	Compound No.	Ar	A	Y	R
Table 573	573-1-573- 710	6- Chloropyridazin- 3-yi	A-1	6- OCH3	represents a combination of substituents corresponding to each row of Table B

139 i

Table 574	574-1-574- 710	2-Chloro-5oxazolyl	A-1	6- OCH3	represents a combination of substituents corresponding to each row of Table B
Table 575	575-1-575- 710	6-trifluoromethyl- 3-pyridyl	A-1	6- OCH3	represents a combination of substituents corresponding to each row of Table B

[Table 19-2]

Table 576	576-1-576- 710	3tetrahydrofuranyi	A-1	6- OCH3	represents a combination of substituents corresponding to each row of Table B
Table 577	577-1-577- 710	2,6-dlchloro-3pyrldyl	A-1	H	represents a combination of substituents corresponding to each row of Table B
Table 578	578-1-578- 710	3-pyridyl	A-1	H	represents a combination of substituents corresponding to each

140

					row of Table B
Table 579	579-1-579- 710	4-pyridyl	A-1	H	represents a combination of substituents corresponding to each row of Table B
[Table 19-3]
Table 580	580-1-580- 710	6-chloro-3pyridyl-N-oxIde	A-1	H	represents a combination of substituents corresponding to each row of Table B

[Table 20-1]

Table B

	R
		oc 1 0=0 1	R1
1		H
2		CF3
3		CHF2
4		CF2CI
5		CF2CF3
6		CH2CI
7		CHCI2
8		CCI3
9		CHCIBr
10		2,2-difluorocyclopropyl
11		2,3,3-trifluoroacryl
12		CH2CHF2
13		CH2CF3
14		CH=CH2
15		CH2C=CH
16		CH2CH2C=CH
		—C-0R_a Ô	R2
17		CH2CF3
18		CH(Me)CF3

141

19		CH(CF3)2
	-9^r3] s I	R3
20		CF3
21		CHF2
22		CF2CI
23		CF2CF3
24		CH2CI
25		CHCI2
26		CCI3
27		CHCIBr
28		CHBr2
29		2,3,3-trlfiuoroacryl
30		CH2CHF2
31		CH2CF3
32		CH=CH2
33		CH2CSCH

[Table 20-2]

34		CH2CF3
35		CH2CH2Ph
36		Me
37		Et
38		n-Pr
39		l-Pr
40		cyclopropyl

[Table 21-1]

Table B

	R
	N 1^4
	R4	R5
41	H	CF3
42	Me	CF3
43	Et	CF3
44	n-Pr	CF3
45	l-Pr	CF3
46	t-Bu	CF3
47	n-Bu	CF3
48	n-Pentyl	CF3
49	n-Hexyi	CF3
50	cyclopropyl	CF3
51	cyclobutyl	CF3
52	cyclopentyl	CF3
53	cyclohexyl	CF3
54	CH=CH2	CF3
55	CH2CH=CH2	CF3
56	CH2C=CH	CF3
57	CH2CH2C=CH	CF3

142

58	CH2CHF2	CF3
59	CH2CCF3	CF3
60	CH2CH2CI	CF3
61	CH2CHCI2	CF3
62	2-fluoro-2chloroethyl	CF3
63	CH2CCI3	CF3
64	CH2CN	CF3
65	CH2CH2CN	CF3
66	CH2CH(CN)CH2C N	CF3
67	CH2CH2OH	CF3
68	CH2CH2CH2OH	CF3
69	CH2CH(OH)CH2O H	CF3
70	CH2CH2NO2	CF3
71	Phenyl	CF3
72	CH2-Phenyl	CF3
73	CH(Me)-Phenyl	CF3
74	C(Me2)-Phenyl	CF3
75	C(cyclopropyl)Phenyl	CF3

[Table 21-2]

76	CH2CH2-Phenyl	CF3
77	CH2-(2Methylphenyl)	CF3
78	CH2-(3Methylphenyl)	CF3
79	CH2-(4Methylphenyl)	CF3
80	CH2-(2Methoxylphenyl)	CF3
81	CH2-(3Methoxylphenyl)	CF3
82	CH2-(4Methoxylphenyl)	CF3
83	CH2-(2fluorolphenyl)	CF3
84	CH2-(3fluorolphenyl)	CF3
85	CH2-(4fluorolphenyl)	CF3
86	CH2-(2Chlorophenyl)	CF3
87	CH2-(3Chlorophenyl)	CF3
88	CH2-(4Chlorophenyl)	CF3
89	CH2-(2Bromophenyl)	CF3
90	CH2-(3Bromophenyl)	CF3
91	CH2-(4-	CF3

143

	Bromophenyl)
92	CH2-(2lodophenyl)	CF3
93	CH2-(3lodophenyl)	CF3

[Table 22-1]

Table B

	R
	-£-R_s N A,
	R4	R5
94	CH2-(4iodophenyl)	CF3
95	CH2-(1 naphthalenyl)	CF3
96	CH2-(2naphthalenyl)	CF3
97	naphthalen-1 ylmethyl	CF3
98	naphthalen-2ylmethyl	CF3
99	quinolin-2- yimethyl	CF3
100	quinolin-7ylmethyl	CF3
101	isoquinolin-7ylmethyl	CF3

144 [Table 22-2]

102	isoquinolln-6ylmethyi	CF3
103	qulnolln-6ylmethyl	CF3
104	quinolin-3ylmethyl	CF3
105	isoquinolin-3yimethyl	CF3
106	isoquinolin-1ylmethyl	CF3
107	isoquinoiin-4yimethyi	CF3
108	quinolin-4yimethyi	CF3
109	qulnolln-5ylmethyl	CF3
110	isoquinolin-5yimethyl	CF3
111	isoquinolin-8ylmethyl	CF3
112	qulnolln-8yimethyl	CF3
113	CH2O-Phenyl	CF3

[Table 22-3]

145

114	CH2CH2O-Phenyl	CF3
115	2-pyrid yl	CF3
116	3-pyrldyi	CF3
117	4-pyridyl	CF3
118	CH2-(2-pyrldyl)	CF3
119	CH2-(3-pyrldyl)	CF3
120	CH2-(4-Chloro-3pyrldyi)	CF3
121	CH2-(4-pyrldyl)	CF3
122	CH2-(2-thienyl)	CF3
123	CH2-(3-thlenyl)	CF3
124	CH2-(2-furanyl)	CF3
125	CH2-(3-furanyl)	CF3
126	CH2-(2- tetrahydrofuranyl)	CF3

[Table 22-4]

127	CH2-(3- tetrahydrofuranyl)	CF3
128	(1H-lmldazol-2- yl)methyl	CF3
129	(1 H-lmldazol-1yl)methyl	CF3
130	(1H-lmldazol-4yl)methyl	CF3
131	CH2-(2-thlazolyl)	CF3

146

132	CH2-(3-thiazolyl)	CF3
133	CH2-(2-pyrrolyi)	CF3
134	CH2-(3-pyrrolyl)	CF3
135	CH2-(5-methylpyrazoi- 1-yi)	CF3
136	CH2-(1-pyrazolyl)	CF3
137	CH2-(2-pyrazolyl)	CF3

[Table 22-5]

138	CH2-(3-pyrazolyi)	CF3
139	CH2-(4-pyrazolyl)	CF3
140	CH2-(5-pyrazolyl)	CF3
141	CH2-(2-oxazolyl)	CF3
142	CH2-(3-oxazolyl)	CF3
143	CH2-(3-lsoxazolyl)	CF3
144	CH2-(4-lsoxazolyi)	CF3
145	CH2-(5-isoxazolyl)	CF3
146	CH2CH2OCH3	CF3
147	CH2CH2OCH2CH3	CF3

[Table 23-1]

Table B

	R
		-Ç-Rs N

147

	R4	R5
148	CH2CH2CH2OCH3	CF3
149	CH2CH2CH2OCH2 CH3	CF3
150	CH2CH2SCH3	CF3
151	CH2CH2SCH2CH3	CF3
152	CH2CH2CH2SCH3	CF3
153	CH2CH2CH2SCH2 CH3	CF3
154	Me	CHF2
155	Et	CHF2
156	n-Pr	CHF2
157	l-Pr	CHF2
158	t-Bu	CHF2
159	n-Bu	CHF2
160	n-Pentyl	CHF2
161	n-Hexyl	CHF2
162	cyclopropyl	CHF2

[Table 23-2]

163	cyclobutyl	CHF2
164	cyclopentyl	CHF2
165	cyclohexyl	CHF2
166	CH=CH2	CHF2
167	CH2CH=CH2	CHF2

148

168	CH2C=CH	CHF2
169	CH2CH2C=CH	CHF2
170	CH2CHF2	CHF2
171	CH2CCF3	CHF2
172	CH2CH2CI	CHF2
173	CH2CHCI2	CHF2
174	2-fluoro-2chloroethyl	CHF2
175	CH2CCI3	CHF2
176	CH2CH2CN	CHF2
177	CH2CH2CH2CN	CHF2
178	CH2CH(CN)CH2C N	CHF2
179	CH2CH2OH	CHF2
180	CH2CH2CH2OH	CHF2
181	CH2CH(OH)CH2 OH	CHF2

[Table 23-3]

182	CH2CH2NO2	CHF2
183	Phenyl	CHF2
184	CH2-Phenyl	CHF2
185	CH(Me)-Phenyl	CHF2
186	C(Me2)-Phenyl	CHF2
187	C(cyclopropyl)Phenyl	CHF2

149

188	CH2CH2-Phenyl	CHF2
189	CH2-(2- Methylphenyl)	CHF2
190	CH2-(3- Methylphenyl)	CHF2
191	CH2-(4- Methylphenyl)	CHF2
192	CH2-(2- Methoxylphenyl)	CHF2
193	CH2-(3- Methoxylphenyl)	CHF2
194	CH2-(4- Methoxylphenyl)	CHF2
195	CH2-(2fluorolphenyl)	CHF2

[Table 23-4]

196	CH2-(3fluorolphenyl)	CHF2
197	CH2-(4fluorolphenyl)	CHF2
198	CH2-(2-Chlorophen yi)	CHF2
199	CH2-(3- Chlorophenyl)	CHF2

150

200	CH2-(4- Chlorophenyl)	CHF2
201	CH2-(2- Bromophenyl)	CHF2

[Table 24-1]

Table B

	R
	-Ç-R» N
	R4	R5
202	CH2-(3- Bromophenyl)	CHF2
203	CH2-(4- Bromophenyl)	CHF2
204	CH2-(2lodophenyl)	CHF2
205	CH2-(3lodophenyl)	CHF2
206	CH2-(4lodophenyl)	CHF2
207	CH2-(1naphthalenyl)	CHF2
208	CH2-(2naphthalenyl)	CHF2

151

209	naphthalen-1ylmethyl	CHF2
210	naphthalen-2ylmethyl	CHF2

[Table 24-2]

211	qulnolln-2ylmethyl	CHF2
212	qulnolln-7ylmethyl	CHF2
213	lsoqulnolln-7ylmethyl	CHF2
214	isoqulnolln-6ylmethyl	CHF2
215	qulnolin-6ylmethyl	CHF2
216	qulnolln-3ylmethyl	CHF2
217	isoqulnolin-3ylmethyl	CHF2
218	lsoqulnolln-1 ylmethyl	CHF2
219	lsoqulnolln-4ylmethyl	CHF2
220	quinolln-4ylmethyl	CHF2

152

221

qulnolln-5ylmethyl

CHF2

[Table 24-3]

222	lsoqulnolln-5ylmethyl	CHF2
223	lsoqulnolin-8ylmethyl	CHF2
224	qulnolln-8ylmethyl	CHF2
225	CH2O-Phenyl	CHF2
226	CH2CH2O-Phenyl	CHF2
227	2-pyrldyl	CHF2
228	3-pyrldyl	CHF2
229	4-pyrldyl	CHF2
230	CH2-(2-pyridyl)	CHF2
231	CH2-(3-pyrldyl)	CHF2
232	CH2-(4-Chloro-3pyrldyl)	CHF2
233	CH2-(4-pyrldyl)	CHF2
234	CH2-(2-thienyi)	CHF2

[Table 24-4]

235	CH2-(3-thlenyl)	CHF2
236	CH2-(2-furanyl)	CHF2
237	CH2-(3-furanyl)	CHF2

153

238	CH2-(2- tetrahydrofuranyl)	CHF2
239	CH2-(3- tetrahydrofuranyl)	CHF2
240	(1H-imidazol-2yljmethyl	CHF2
241	(1H-lmidazol-1yljmethyl	CHF2
242	(1H-lmidazol-4yl)methyl	CHF2
243	CH2-(2-thlazolyl)	CHF2
244	CH2-(3-thlazolyl)	CHF2
245	CH2-(2-pyrroiyi)	CHF2

[Table 24-5]

246	CH2-(3-pyrroiyl)	CHF2
247	CH2-(5methylpyrazol-1yi)	CHF2
248	CH2-(1-pyrazoiyl)	CHF2
249	CH2-(2-pyrazoiyi)	CHF2
250	CH2-(3-pyrazolyl)	CHF2
251	CH2-(4-pyrazolyi)	CHF2
252	CH2-(5-pyrazolyi)	CHF2
253	CH2-(2-oxazolyl)	CHF2

154

254	CH2-(3-oxazolyl	CHF2
255	CH2-(3- Isoxazolyl)	CHF2

[Table 25-1]

Table B

	R
	-Ç-Rs N A.
	R4	R5
256	CH2-(4-isoxazolyl)	CHF2
257	CH2-(5-lsoxazolyl)	CHF2
258	CH2CH2OCH3	CHF2
259	CH2CH2OCH2CH3	CHF2
260	CH2CH2CH2OCH3	CHF2
261	CH2CH2CH2OCH2 CH3	CHF2
262	CH2CH2SCH3	CHF2
263	CH2CH2SCH2CH3	CHF2
264	CH2CH2CH2SCH3	CHF2
265	CH2CH2CH2SCH2 CH3	CHF2
266	Me	CF2CI
267	Et	CF2CI
268	n-Pr	CF2CI

155 [Table 25-2]

269	l-Pr	CF2CI
270	t-Bu	CF2CI
271	n-Bu	CF2CI
272	n-Pentyl	CF2CI
273	n-Hexyl	CF2CI
274	cyclopropyl	CF2CI
275	cyclobutyl	CF2CI
276	cyclopentyl	CF2CI
277	cyclohexyl	CF2CI
278	CH=CH2	CF2CI
279	CH2CH=CH2	CF2CI
280	CH2C=CH	CF2CI
281	CH2CH2C=CH	CF2CI
282	CH2CHF2	CF2CI
283	CH2CCF3	CF2CI
284	CH2CH2CI	CF2CI
285	CH2CHCI2	CF2CI
286	2-fluoro-2chloroethyl	CF2CI
287	CH2CCI3	CF2CI
288	CH2CH2CN	CF2CI
289	CH2CH2CH2CN	CF2CI

[Table 25-3]

156

290	CH2CH(CN)CH2C N	CF2CI
291	CH2CH2OH	CF2CI
292	CH2CH2CH2OH	CF2CI
293	CH2CH(OH)CH2O H	CF2CI
294	CH2CH2NO2	CF2CI
295	Phenyl	CF2CI
296	CH2-Phenyl	CF2CI
297	CH(Me)-Phenyl	CF2CI
298	C(Me2)-Phenyl	CF2CI
299	C(cyclopropyl)- Phenyl	CF2CI
300	CH2CH2-Phenyl	CF2CI
301	CH2-(2- Methylphenyl)	CF2CI
302	CH2-(3- Methylphenyl)	CF2CI
303	CH2-(4- Methylphenyl)	CF2CI
304	CH2-(2- Methoxylphenyl)	CF2CI

[Table 25-4]

305

CH2-(3- Methoxylphenyl)

CF2CI

157

306	CH2-(4- Methoxylphenyl)	CF2CI
307	CH2-(2-fluorolphenyl)	CF2CI
308	CH2-(3-fluorolphenyl)	CF2CI
309	CH2-(4-fluorolphenyl)	CF2CI

[Table 26-1J

Table B

	R
	I ?»-z=o X w
	R4	R5
310	CH2-(2- Chlorophenyl)	CF2CI
311	CH2-(3- Chlorophenyl)	CF2CI
312	CH2-(4- Chlorophenyl)	CF2CI
313	CH2-(2- Bromophenyl)	CF2CI
314	CH2-(3Bromophenyl)	CF2CI
315	CH2-(4- Bromophenyl)	CF2CI

158

316	CH2-(2lodophenyl)	CF2CI
317	CH2-(3lodophenyl)	CF2CI
318	CH2-(4iodophenyl)	CF2CI

[Table 26-2]

319	CH2-(1naphthalenyl)	CF2CI
320	CH2-(2- naphthalenyl)	CF2CI
321	naphthalen-1ylmethyl	CF2CI
322	naphthalen-2ylmethyl	CF2CI
323	quinolin-2ylmethyl	CF2CI
324	quinolin-7ylmethyl	CF2CI
325	lsoquinolln-7ylmethyl	CF2CI
326	lsoqulnolln-6ylmethyl	CF2CI
327	qulnolln-6ylmethyl	CF2CI

159

328	quinolin-3ylmethyl	CF2CI
329	lsoquinolin-3ylmethyl	CF2CI

[Table 26-3J

330	lsoqulnoiln-1ylmethyl	CF2CI
331	isoq uinolin-4ylmethyl	CF2CI
332	quinolln-4ylmethyl	CF2Ci
333	qulnoiln-5ylmethyi	CF2CI
334	isoquinolln-5ylmethyl	CF2Ci
335	isoquinoiin-8ylmethyl	CF2CI
336	quinoiln-8ylmethyi	CF2CI
337	CH2O-Phenyl	CF2CI
338	CH2CH2O-Phenyl	CF2CI
339	2-pyrldyl	CF2CI
340	3-pyridyl	CF2CI
341	4-pyridyl	CF2CI

160

342

CH2-(2-pyrldyl)

CF2CI

[Table 26-4]

343	CH2-(3-pyrldyl)	CF2CI
344	CH2-(4-Chloro-3pyridyl)	CF2CI
345	CH2-(4-pyrldyl)	CF2CI
346	CH2-(2-thienyl)	CF2CI
347	CH2-(3-thienyl)	CF2CI
348	CH2-(2-furanyl)	CF2CI
349	CH2-(3-furanyl)	CF2CI
350	CH2-(2- tetrahydrofuranyl)	CF2CI
351	CH2-(3- tetrahydrofuranyl)	CF2CI
352	(1H-imidazol-2- yl)methyl	CF2CI
353	(1H-lmldazol-1yl)methyl	CF2CI

[Table 26-5]

354	(1H-lmldazol-4yl)methyl	CF2CI
355	CH2-(2-thiazolyl)	CF2CI
356	CH2-(3-thiazoiyl)	CF2CI

161

357	CH2-(2-pyrrolyl)	CF2CI
358	CH2-(3-pyrrolyl)	CF2CI
359	CH2-(1-pyrazolyl)	CF2CI
360	CH2-(2-pyrazolyl)	CF2CI
361	CH2-(3-pyrazolyl)	CF2CI
362	CH2-(4-pyrazolyl)	CF2CI
363	CH2-(5-pyrazolyl)	CF2CI

[Table 27-1]

Table B

	R
	I ?-²=? 2
	R4	R5
364	CH2-(5- pyrazolyl)	CF2CI
365	CH2-(2-oxazolyl)	CF2CI
366	CH2-(3-oxazolyl)	CF2CI
367	CH2-(3isoxazolyl)	CF2CI
368	CH2-(4- isoxazolyl)	CF2CI
369	CH2-(5isoxazolyl)	CF2CI
370	CH2CH2OCH3	CF2CI

162

371	CH2CH2OCH2C H3	CF2CI
372	CH2CH2CH2OC H3	CF2CI

[Table 27-2]

373	CH2CH2CH2OC H2CH3	CF2CI
374	CH2CH2SCH3	CF2C!
375	CH2CH2SCH2C H3	CF2C!
376	CH2CH2CH2SC H3	CF2CI
377	CH2CH2CH2SC H2CH3	CF2CI
378	Me	CF2CF3
379	Et	CF2CF3
380	n-Pr	CF2CF3
381	l-Pr	CF2CF3
382	t-Bu	CF2CF3
383	n-Bu	CF2CF3
384	n-Pentyl	CF2CF3
385	n-Hexyl	CF2CF3
386	cyclopropyl	CF2CF3
387	cyclobutyl	CF2CF3

163

388	cyclopentyl	CF2CF3
389	cyclohexyl	CF2CF3
390	CH=CH2	CF2CF3

[Table 27-3]

391	CH2CH=CH2	CF2CF3
392	CH2C5CH	CF2CF3
393	CH2CH2C=CH	CF2CF3
394	CH2CHF2	CF2CF3
395	CH2CCF3	CF2CF3
396	CH2CH2CI	CF2CF3
397	CH2CHCI2	CF2CF3
398	2-fluoro-2chloroethyl	CF2CF3
399	CH2CCI3	CF2CF3
400	CH2CH2CN	CF2CF3
401	CH2CH2CH2CN	CF2CF3
402	CH2CH(CN)CH2 CN	CF2CF3
403	CH2CH2OH	CF2CF3
404	CH2CH2CH2OH	CF2CF3
405	CH2CH(OH)CH2 OH	CF2CF3
406	CH2CH2NO2	CF2CF3
407	Phenyl	CF2CF3

164

408

CH2-Phenyl

CF2CF3

[Table 27-4]

409	CH(Me)-Phenyl	CF2CF3
410	C(Me2)-Phenyl	CF2CF3
411	C(cyclopropyl)Phenyl	CF2CF3
412	CH2CH2-Phenyl	CF2CF3
413	CH2-(2- Methylphenyl)	CF2CF3
414	CH2-{3- Methylphenyl)	CF2CF3
415	CH2-(4- Methylphenyl)	CF2CF3
416	CH2-(2- Methoxylphenyl)	CF2CF3
417	CH2-(3- Methoxylphenyl)	CF2CF3

[Table 28-1]

Table B

	R
		—C-Rj il · N A4
	R4	R5

165

418	CH2-(4- Methoxylphenyl)	CF2CF3
419	CH2-(2-fluorolphenyl)	CF2CF3
420	CH2-(3-fluorolphenyl)	CF2CF3
421	CH2-(4-fluorolphenyl)	CF2CF3
422	CH2-(2-Chlorophenyl)	CF2CF3
423	CH2-(3-Chlorophenyl)	CF2CF3
424	CH2-(4-Chlorophenyl)	CF2CF3
425	CH2-(2-Bromophenyl)	CF2CF3
426	CH2-(3-Bromophenyl)	CF2CF3

[Table 28-2]

427	CH2-(4- Bromophenyl)	CF2CF3
428	CH2-(2-lodophenyl)	CF2CF3
429	CH2-(3-lodophenyl)	CF2CF3
430	CH2-(4-lodophenyl)	CF2CF3
431	CH2-(1naphthalenyl)	CF2CF3
432	CH2-(2naphthalenyl)	CF2CF3
433	naphthalen-1ylmethyl	CF2CF3
434	naphthalen-2ylmethyl	CF2CF3
435	qulnolln-2-ylmethyl	CF2CF3

166

436	qulnolin-7-ylmethyl	CF2CF3
437	lsoqulnolln-7ylmethyl	CF2CF3

[Table 28-3]

438	lsoqulnolln-6ylmethyl	CF2CF3
439	qulnolin-6ylmethyl	CF2CF3
440	quinolin-3ylmethyl	CF2CF3
441	isoquinolin-3ylmethyl	CF2CF3
442	isoquinolin-1ylmethyl	CF2CF3
443	lsoqulnolln-4ylmethyl	CF2CF3
444	qulnolln-4ylmethyl	CF2CF3
445	qulnolln-5ylmethyl	CF2CF3
446	isoquinolin-5ylmethyl	CF2CF3
447	lsoqulnolin-8ylmethyl	CF2CF3

167

448	qulnolln-8ylmethyl	CF2CF3
449	CH20-Phenyl	CF2CF3

fiable 28-4]

450	CH2CH2O-Phenyl	CF2CF3
451	2-pyrldyl	CF2CF3
452	3-pyridyl	CF2CF3
453	4-pyrldyl	CF2CF3
454	CH2-(2-pyrldyl)	CF2CF3
455	CH2-( 3-pyridyl )	CF2CF3
456	CH2-(4-Chloro-3pyridyl)	CF2CF3
457	CH2-(4-pyridyl)	CF2CF3
458	CH2-(2-thlenyl)	CF2CF3
459	CH2-(3-thlenyl)	CF2CF3
460	CH2-(2-furanyl)	CF2CF3
461	CH2-(3-furanyl)	CF2CF3
462	CH2-(2tetrahydrofuranyl)	CF2CF3

[Table 28-5]

463	CH2-(3- tetrahydrofuranyl)	CF2CF3
464	(1H-lmldazol-2yljmethyl	CF2CF3

168

465	(1H-lmldazol-1ylmethyl	CF2CF3
466	(1H-lmldazol-4- yl)methyl	CF2CF3
467	CH2-(2-thlazolyl)	CF2CF3
466	CH2-(3-thlazolyl)	CF2CF3
469	CH2-(2-pyrrolyl)	CF2CF3
470	CH2-(3-pyrrolyl)	CF2CF3
471	CH2-(5-methyl pyrazolyl-1-yl)	CF2CF3

[Table 29-1]

Table B

	R
	À.
	R4	R5
472	CH2-(1-pyrazolyl)	CF2CF3
473	CH2-(2-pyrazolyl)	CF2CF3
474	CH2-(3-pyrazolyl)	CF2CF3
475	CH2-(4-pyrazolyl)	CF2CF3
476	CH2-(5-pyrazolyi)	CF2CF3
477	CH2-(2-oxazolyl)	CF2CF3
478	CH2-(3-oxazoiyl)	CF2CF3
479	CH2-(3-lsoxazolyl)	CF2CF3

169

480

CH2-(4-lsoxazolyl)

CF2CF3

[Table 29-2]

481	CH2-(5-lsoxazolyl)	CF2CF3
482	CH2CH2OCH3	CF2CF3
483	CH2CH2OCH2CH 3	CF2CF3
484	CH2CH2CH2OCH 3	CF2CF3
485	CH2CH2CH2OCH 2CH3	CF2CF3
486	CH2CH2SCH3	CF2CF3
487	CH2CH2SCH2CH3	CF2CF3
488	CH2CH2CH2SCH3	CF2CF3
489	CH2CH2CH2SCH2 CH3	CF2CF3
490	Me	CH2CF3
491	Et	CH2CI
492	n-Pr	CHCI2
493	l-Pr	CCI3
494	t-Bu	CHCIBr
495	n-Bu	CHBr2
496	n-Pentyl	CH=CH2
497	n-Hexyl	CH2CH=CH2
498	cyclopropyl	CH2C=CH

170 [Table 29-3]

	—C-R, a ÔR,
	R6	R7
499	H	CF3
500	Me	CF3
501	Et	CF3
502	n-Pr	CF3
503	l-Pr	CF3
504	t-Bu	CF3
505	cyclopropyl	CF3
506	CH=CH2	CF3
507	CH2CH=CH2	CF3
508	CH2C=CH	CF3
509	Ph	CF3
510	CH2Ph	CF3
511	COMe	CF3
512	COEt	CF3
513	CO-n-Pr	CF3
514	CO-l-Pr	CF3
515	CO-cyclopropyl	CF3
516	COCH=CH2	CF3

[Table 29-4]

517

COCH2CH=CH2

CF3

171

518	COCH2C=CH	CF3
519	COPh	CF3
520	CO-(2-pyrldyl)	CF3

(Table 30-1]

Table B

	R
	-ç-R» N ÔR#
	R6	R7
521	CO-(3-pyrldyl)	CF3
522	CO-(4-pyrldyl)	CF3
523	COOMe	CF3
524	COOEt	CF3
525	COO-l-Pr	CF3
526	COO-t-Bu	CF3
527	COOPh	CF3
528	SO2Me	CF3
529	S02Et	CF3
530	SO2Ph	CF3
531	SO2-(4methylphenyl)	CF3
532	NHMe	CF3
533	NHEt	CF3
534	NH-n-Pr	CF3

172 [Table 30-21

535	NHCH2CH2CI	CF3
536	NHCH2Ph	CF3
537	N(Me)2	CF3
538	Me	CHF2
539	Et	CHF2
540	n-Pr	CHF2
541	l-Pr	CHF2
542	t-Bu	CHF2
543	cyciopropyi	CHF2
544	CH=CH2	CHF2
545	CH2CH=CH2	CHF2
546	CH2C=CH	CHF2
547	Ph	CHF2
548	CH2Ph	CHF2
549	COMe	CHF2
550	COEt	CHF2
551	CO-n-Pr	CHF2
552	CO-l-Pr	CHF2
553	CO-cyclopropyl	CHF2
554	COCH=CH2	CHF2
555	COCH2CH=CH2	CHF2

[Table 30-31

173

556	COCH2C=CH	CHF2
557	COPh	CHF2
558	CO-(2-pyridyl)	CHF2
559	CO-(3-pyrldyi)	CHF2
560	CO-(4-pyrldyl)	CHF2
561	COOMe	CHF2
562	COOEt	CHF2
563	COO-i-Pr	CHF2
564	COO-t-Bu	CHF2
565	COOPh	CHF2
566	SO2Me	CHF2
567	SO2Et	CHF2
568	SO2Ph	CHF2
569	SO2-(4methylphenyl)	CHF2
570	Me	CF2CI
571	Et	CF2CI
572	n-Pr	CF2CI
573	l-Pr	CF2CI

[Table 30-4]

574

t-Bu

CF2CI

174 [Table 31-1]

Table B

	R
	—C-Rj A Ôr«
	R6	R7
575	cyclopropyl	CF2CI
576	CH=CH2	CF2CI
577	CH2CH=CH2	CF2CI
578	CH2CSCH	CF2CI
579	Ph	CF2CI
580	CH2Ph	CF2CI
581	COMe	CF2CI
582	COEt	CF2CI
583	CO-n-Pr	CF2CI
584	CO-l-Pr	CF2CI
585	CO-cyclopropyl	CF2CI
586	COCH=CH2	CF2CI
587	COCH2CH=CH2	CF2CI
588	COCH2CECH	CF2CI
589	COPh	CF2CI

175 [Table 31-2]

590	CO-(2-pyridyl)	CF2CI
591	CO-(3-pyrldyl)	CF2CI
592	CO-(4-pyridyl)	CF2CI
593	COOMe	CF2CI
594	COOEt	CF2CI
595	COO-i-Pr	CF2CI
596	COO-t-Bu	CF2CI
597	COOPh	CF2CI
598	SO2Me	CF2CI
599	SO2Et	CF2CI
600	SO2Ph	CF2CI
601	SO2-(4methylphenyl)	CF2CI
602	Me	CF2CF3
603	Et	CF2CF3
604	n-Pr	CF2CF3
605	i-Pr	CF2CF3
606	t-Bu	CF2CF3
607	cyclopropyl	CF2CF3

[Table 31-3]

608	CH=CH2	CF2CF3
609	CH2CH=CH2	CF2CF3
610	CH2CSCH	CF2CF3

176

611	Ph	CF2CF3
612	CH2Ph	CF2CF3
613	COMe	CF2CF3
614	COEl	CF2CF3
615	CO-n-Pr	CF2CF3
616	CO-t-Pr	CF2CF3
617	CO-cyclopropyl	CF2CF3
618	COCH=CH2	CF2CF3
619	COCH2CH=CH2	CF2CF3
620	COCH2C=CH	CF2CF3
621	COPh	CF2CF3
622	C0-(2-pyrldyl)	CF2CF3
623	C0-(3-pyrtdyl)	CF2CF3
624	C0-(4-pyrldyl)	CF2CF3
625	COOMe	CF2CF3

[Table 31-4]

626	COOEt	CF2CF3
627	COO-l-Pr	CF2CF3

[Table 32]

Table B

	R
		—C-Rj II N ÔR«

177

	R6	R7
628	COO-t-Bu	CF2CF3
629	COOPh	CF2CF3
630	SO2Me	CF2CF3
631	S02Et	CF2CF3
632	SO2Ph	CF2CF3
633	SO2-(4-methylphenyl)	CF2CF3
634	Me	CH2CF3
635	Et	CH2CI
636	n-Pr	CHCI2
637	i-Pr	CCI3
638	t-Bu	CHCIBr
639	cyclopropyl	CHBr2
640	CH=CH2	CH=CH2
641	CH2CH-CH2	CH2CH=CH2
642	CH2C=CH	CH2C=CH

[Table 33]

Table B

	R
	—C-R) 0
		R1
643		C6F5
644		CH2OCH2C6H5
	—c-or₂ Il * 0
		R2
645		CH2C6H5
646		Isopropyl
647		CH2CH2CH=CH2

178

	—c-r₃1« * S
		R3
648		C6F5
649		CH2OCH2C6H5

[Table 34-11

Table B

	R
	-c-Rj N A4
	R4	R5
650	Ethyl	CH2CF3
651	n-Propyl	CH2CF3
652	Iso-Propyl	CH2CF3
653	t-Butyl	CH2CF3
654	n-Butyl	CH2CF3
655	cyclopropyl	CH2CF3
656	cyclopentyl	CH2CF3
657	cyclohexyl	CH2CF3
658	n-hexa decyl	CF3
659	n-trldecyl	CF3
660	CH(CH3)CH2CH3	CF3
661	CH(CH3)CH2CH2CH3	CF3
662	CH(CH3)-isopropyl	CF3
663	1-phenylethyl	CF3
664	1.2.3.4tetrahydronaphthalen-1yi	CF3
665	1-{naphthalen-1-yl)ethyl	CF3
666	1-(naphthalen-1-yl)propyl	CF3
667	1-{furan-2-yl)ethyl	CF3

179

668	3.3-dlmethylbutan-2-yl	CF3
669	1-(thiophen-2-yl)ethyl	CF3

[Table 34-2]

670	CH2CH2F	CF3
671	n-Octyl	CF3
672	n-Octyl	CHF2
673	n-Octyl	CF2CI
674	n-Octyl	CF2CF3
675	n-Octyl	CF2CF3
676	CH(C6H5)2	CF3
677	CH(C6H5)2	CHF2
678	CH(C6H5)2	CF2CI
679	CH(C6H5)2	CF2CF3
680	CH(C6H5)2	CH2CF3
681	CH(CH2CH3)2	CF3
682	CH(CH2CH3)2	CHF2
683	CH(CH2CH3)2	CF2CI
684	CH(CH2CH3)2	CF2CF3
685	CH(CH2CH3)2	CH2CF3
686	CH(CH2CH2CH3)2	CF3
687	CH(CH2CH2CH3)2	CHF2
688	CH(CH2CH2CH3)2	CF2CI
689	CH(CH2CH2CH3)2	CF2CF3
690	CH(CH2CH2CH3)2	CF2CF3

180 [Table 35-1]

Table B

	R
	Xi Ry -ρ-γ₂ ^YîHy
	Y1	Y2	Ry
691	0	0	Methyl
692	0	0	Ethyl
693	0	0	Propyl
694	0	0	Isopropyl
695	S	0	Methyl
696	S	0	Ethyl
697	S	0	Propyl
698	S	0	Isopropyl
699	S	S	Methyl
700	S	S	Ethyl
701	S	S	Propyl
702	S	S	isopropyl
	-S-Rz [ôl_B
	n	Rz
703	1	CF3
704	1	CF2CF3

[Table 35-2]

181

705	1	CH2CF3
706	1	Me
707	2	CF3
708	2	CF2CF3
709	2	CH2CF3
710	2	Me

Examples of preferred compounds of Formula (I) Include compounds shown In the following Tables.

[Table 36-1]

Compo und No	Ar	A	Y	R
266-2	6-Chloro-3-pyrldyl	A- 38	H	COCF3
444-2	2-chloro-5-thlazolyl	A- 38	H	COCF3
190-2	6-Chloro-3-pyridyl	A- 13	H	COCF3
201-2	6-Chloro-3-pyrldyl	A- 14	H	COCF3
223-2	6-Chloro-3-pyrldyl	A- 16	H	COCF3
146-2	6-Chloro-3-pyrldyi	A-1	3- OH	COCF3
224-2	2-chloro-5-thlazoiyl	A- 16	H	COCF3

182

102-2	6-Chloro-3-pyrldyl	A-1	3- CN	COCF3
212-2	6-Chloro-3-pyridyl	A- 15	H	COCF3
1-20	6-Chloro-3-pyridyl	A-1	H	CSCF3

[Table 36-2]

12-2	2-Chloro-4-pyrldyi	A-1	H	COCF3
213-2	2-chloro-5-thiazolyl	A- 15	H	COCF3
1-17	6-Chloro-3-pyrldyl	A-1	H	COOCH2CF3
1-18	6-Chioro-3-pyridyl	A-1	H	COOCH(Me)CF3
1-19	6-Chloro-3-pyridyl	A-1	H	COOCH(CF3)2
7-2	5-Chloropyrazin-2-yl	A-1	H	COCF3
1-13	6-Chloro-3-pyrldyl	A-1	H	COCH2CF3
168-2	6-Chloro-3-pyrldyl	A-1	5- OH	COCF3
1-21	6-Chloro-3-pyrldyl	A-1	H	CSCHF2
3-20	6-Fiuoro-3-pyridyl	A-1	H	CSCF3
4-20	6-Bromo-3-pyridyl	A-1	H	CSCF3

[Table 36-3]

3-3	6-Fluoro-3-pyridyl	A- 1	H	COCHF2
4-3	6-Bromo-3-pyridyl	A- 1	H	COCHF2

183

5-5	6-Chloro-5-fluoro-3- pyridyl	A- 1	H	COCF2CF3
6-5	2-Chloro-5-pyrlmidinyi	A- 1	H	COCF2CF3
1-22	6-Chloro-3-pyrldyl	A- 1	H	CSCF2CI
1-23	6-Chloro-3-pyrldyl	A- 1	H	CSCF2CF3
5-20	6-Chloro-5-fluoro-3pyrldyl	A- 1	H	CSCF3
5-3	6-Chloro-5-fluoro-3- pyridyi	A- 1	H	COCHF2
6-3	2-Chloro-5-pyrlmidinyi	A- 1	H	COCHF2
8-2	6-Chloropyrldazln-3-yl	A- 1	H	COCF3
5-4	6-Chloro-5-fluoro-3- pyrldyl	A- 1	H	COCF2CI

[Table 36-4]

4-4	6-Bromo-3-pyrldyl	A-1	H	COCF2CI
6-4	2-Chloro-5pyrîmldlnyl	A-1	H	COCF2CI
4-5	6-Bromo-3-pyrldyl	A-1	H	COCF2CF3
2-20	2-chloro-5-thlazolyl	A-1	H	CSCF3

184

10-20	6-trlfluoromethyl-3pyrldyl	A-1	H	CSCF3
3-4	6-Fluoro-3-pyrldyl	A-1	H	COCF2CI
3-5	6-Fluoro-3-pyrldyl	A-1	H	COCF2CF3
11-20	3-THF	A-1	H	CSCF3
1-14	6-Chloro-3-pyrldyl	A-1	H	COCH=CH2
1-37	6-Chloro-3-pyrldyl	A-1	H	CSEt
1-39	6-Chloro-3-pyrldyl	A-1	H	CS-l-Pr

[Table 36-5]

1-40	6-Chloro-3-pyrldyl	A-1	H	CS-cyclopropyl
1-15	6-Chloro-3-pyrldyl	A-1	H	COCH2C=CH
1-35	6-Chloro-3-pyrldyl	A-1	H	CSCH2CH2Ph
1-501	6-Chloro-3-pyrldyl	A-1	H	C(=NOEt)CF3
1-499	6-Chloro-3-pyridyl	A-1	H	C(=NOH)CF3
1-510	6-Chloro-3-pyrldyl	A-1	H	C(=NOCH2Ph)CF 3
1-511	6-Chloro-3-pyrldyl	A-1	H	C(=NOCOMe)CF3
1-519	6-Chloro-3-pyridyl	A-1	H	C(=NOCOPh)CF3
1-523	6-Chloro-3-pyrldyl	A-1	H	C(-NOCOOMe)C F3

[Table 37-1]

Compoun d No	Ar	A	Y	R
1-528	6-Chloro-3-pyrldyl	A-1	H	C(=NOSO2Me)CF3

185

1-531	6-Chloro-3-pyridyl	A-1	H	C(=NOSO2-(4- Methylphenyl))CF3
1-507	6-Chloro-3-pyridyl	A-1	H	C(=NOCH2CH=CH2)CF3
1-516	6-Chloro-3-pyrldyl	A-1	H	C(=NOCOCH=CH2)CF3
1-518	6-Chloro-3-pyrldyl	A-1	H	C(=NOCOCH2C=CH)CF3
1-527	6-Chloro-3-pyrldyl	A-1	H	C(=NOCOOPh)CF3
1-521	6-Chloro-3-pyridyl	A-1	H	C(=NOCO-3-pyr)CF3
1-43	6-Chloro-3-pyridyl	A-1	H	C(=NEt)CF3
1-536	6-Chloro-3-pyrldyl	A-1	H	C(=NOCONHCH2Ph)CF3
1-42	6-Chloro-3-pyrldyl	A-1	H	C(=NMe)CF3

[Table 37-2]

1-500	6-Chloro-3-pyrldyl	A-1	H	C(=NOMe)CF3
1-504	6-Chloro-3-pyridyl	A-1	H	C(=NOtBu)CF3
1-534	6-Chloro-3-pyrldyl	A-1	H	C(=NOCONHnPr)CF3
1-535	6-Chloro-3-pyridyl	A-1	H	C(=NOCONHCH2CH2CI)CF 3
1-72	6-Chloro-3-pyrldyl	A-1	H	C(=NCH2Ph)CF3
1-150	6-Chloro-3-pyridyl	A-1	H	C(=NCH2CH2SMe)CF3
1-67	6-Chloro-3-pyrldyl	A-1	H	C(=NCH2CH2OH)
1-515	6-Chloro-3-pyridyl	A-1	H	C(=NOCO-cyclopropyl)CF3
1-56	6-Chloro-3-pyrldyl	A-1	H	C(=NCH2C = CH)CF3
1-512	6-Chloro-3-pyridyl	A-1	H	C(=NOCOCH2CH3)CF3
1-514	6-Chloro-3-pyridyl	A-1	H	C(=NOCOIPr)CF3

1Θ6 [Table 37-3]

1-50	6-Chloro-3-pyrldyl	A-1	H	C(=N-cyc!opropyl)CF3
1-114	6-Chloro-3-pyrldyl	A-1	H	C(=NCH2CH2OPh)CF3
1-44	6-Chloro-3-pyrldyl	A-1	H	C(=N-n-Pr)CF3
1-118	6-Chloro-3-pyridyl	A-1	H	C(=NCH2-(2-pyrldyl))CF3
1-119	6-Chloro-3-pyrldyl	A-1	H	C(=NCH2-(3-pyridyl))CF3
1-47	6-Chloro-3-pyridyl	A-1	H	C(=N-n-Bu)CF3
1-55	6-Chloro-3-pyrldyl	A-1	H	C(=N-CH2CH=CH2)CF3
1-122	6-Chloro-3-pyrldyl	A-1	H	C(=NCH2-(2-thienyl))CF3
1-45	6-Chioro-3-pyridyl	A-1	H	C(=N-l-Pr)CF3
1-124	6-Chloro-3-pyridyl	A-1	H	C(=NCH2-(2-furanyl))CF3
1-126	6-Chloro-3-pyrldyl	A-1	H	C(=NCH2-(2- tetrahydrofuranyl))CF3

[Table 37-4]

1-64	6-Chloro-3-pyridyl	A-1	H	C(=NCH2CN)CF3
1-146	6-Chloro-3-pyridyl	A-1	H	C(=NCH2CH2OCH3)CF3
1-52	6-Chloro-3-pyridyl	A-1	H	C(=N-cyclopentyl)CF3
1-121	6-Chloro-3-pyridyl	A-1	H	C(=NCH2-(4-pyridyl))CF3
1-53	6-Chloro-3-pyridyl	A-1	H	C(=N-cyclohexyl)CF3
1-76	6-Chloro-3-pyrldyl	A-1	H	C(=NCH2CH2Ph)CF3
267-2	6-Chloro-3-pyrldyl	A- 39	H	COCF3
253-2	6-Chloro-3-pyrldyl	A- 25	H	COCF3

187

251-2	6-Chloro-3-pyrldyl	A- 23	H	C0CF3
13-2	3-Cyanophenyl	A-1	H	C0CF3
1-1	6-Chloro-3-pyridyl	A-1	H	CHO
1-41	6-Chloro-3-pyrldyl	A-1	H	C(=NH)CF3

[Table 38-1]

Compo und No.	Ar	A	Y	R
1-647	6-Chloro-3-pyrldyl	A-1	H	COOCH2CH2CH=CH2
1-670	6-Chioro-3-pyridyl	A-1	H	C(-NCH2CH2F)CF3
157-2	6-Chioro-3-pyridyl	A-1	4-OH	COCF3
1-10	6-Chloro-3-pyridyl	A-1	H	CO(2,2-dlfluonocyclopropyl)
580-2	6-chloro-3-pyridyl- N-oxid	A-1	H	COCF3
1-671	6-Chloro-3-pyridyl	A-1	H	C(=N(CH2)7CH3)CF3
1-658	6-Chloro-3-pyridyl	A-1	H	C(=N(CH2)15CH3)CF3
1-659	6-Chloro-3-pyridyl	A-1	H	C(=N(CH2)11CH3)CF3
1-660	6-Chloro-3-pyridyi	A-1	H	C(=NCH(CH3)CH2CH3)CF3

[Table 38-2]

1-681	6-Chioro-3-pyridyl	A-1	H	C(=NCH(CH2CH3)2)CF3
1-686	6-Chloro-3-pyridyi	A-1	H	C(=NCH(CH2CH2CH3)2)CF3
1-661	6-Chloro-3-pyridyl	A-1	H	C(=NCH(CH3)CH2CH2CH3)CF3
1-662	6-Chioro-3-pyridyl	A-1	H	C(=NCH(lso-propyl)CH3)CF3
1-663	6-Chloro-3-pyridyi	A-1	H	C(=N(1-phenyiethyi))CF3

188

1-664	6-Chloro-3-pyrldyl	A-1	H	C(=N(1,2,3,4tetrahydronaphthalen-1-yl)CF3
1-665	6-Chloro-3-pyridyl	A-1	H	C(=N(1-(naphthalen-1 yi)ethyl))CF3
1-666	6-Chloro-3-pyridyi	A-1	H	C(=N(1-(naphthalen-1yl )p ropyl) )CF3
1-667	6-Chloro-3-pyridyl	A-1	H	C(=N(1-(furan-2-yl)ethyi))CF3
1-676	6-Chloro-3-pyrldyl	A-1	H	C(=NCH(C6H5)2)CF3
1-668	6-Chloro-3-pyridyl	A-1	H	C(=N(3,3-dimethylbutan-2- yl))CF3

[Table 38-3]

47-2	6-Chloro-3-pyridyl	A-1	6-F	C0CF3
91-2	6-Chloro-3-pyridyl	A-1	6-CI	COCF3
478-2	6-Chloro-3-pyridyl	A-1	6-CH3	C0CF3
479-2	2-Chloro-5- thlazolyl	A-1	6-CH3	C0CF3
1-51	6-Chloro-3-pyridyl	A-1	H	C(=N-cyclobutyl)CF3
566-2	6-Chloro-3-pyridyl	A-1	6- CH30	COCF3
488-2	3tetrahydrofuranyl	A-1	6-CH3	C0CF3
511-2	6-Chloro-3-pyridyl	A-1	5- NO2	COCF3
1-669	6-Chloro-3-pyrldyl	A-1	H	C(=N(1-(thiophen-2- yl)ethyl))CF3

189

179-2	6-Chloro-3-pyrldyl	A-1	6-OH	COCF3 (also represents a tautomer)
555-2	6-Chloro-3-pyridyl	A-1	5- OCH3	COCF3

[Table 38-41

577-2	2,6-dlchrolo-3pyrldyl	A-1	H	COCF3
544-2	6-Chloro-3-pyrldyl	A-1	4- OCH3	COCF3
168-2	6-Chloro-3-pyrldyl	A-1	5-OH	COCF3
1-644	6-Chloro-3-pyrldyl	A-1	H	COCH2OCH2C6H5
578- 644	3-pyrldyl	A-1	H	COCH2OCH2C6H5
1-703	6-Chloro-3-pyrldyl	A-1	H	SOCF3
1-707	6-Chloro-3-pyridyl	A-1	H	SO2CF3
1-706	6-Chloro-3-pyrldyl	A-1	H	SOCH3
1-692	6-Chloro-3-pyrldyl	A-1	H	P(=0)(0Et)2
1-700	6-Chloro-3-pyrldyl	A-1	H	P(=S)(SEt)2
1-701	6-Chloro-3-pyrldyl	A-1	H	P(=S)(S-n-propyl)2

[Table 38-5]

1-702	6-Chloro-3-pyrldyl	A-1	H	P(=S)(S-isopropyl)2
1-646	6-Chloro-3-pyrldyl	A-1	H	COO-lso-Pr
1-645	6-Chloro-3-pyrldyl	A-1	H	COOCH2C6H5
1-643	6-Chloro-3-pyridy!	A-1	H	COC6F5

190

2-643

2-Chloro-5thlazolyl

A-1

H

COC6F5

[Table 39-1]

Compound No.	Ar	R1a	Y
P212	6-chloro-3-pyridyl	CF3	H
P213	2-chloro-5-thlazolyl	CF3	H
P214	6-chloro-3-pyridyl	OCH3	H
P215	6-chloro-3-pyridyl	CF3	5Cl
P216	6-chloro-3-pyridyl	CF3	5F
P217	6-ch!oro-3-pyrldyl	CF3	4Cl
P218	2-ch!oro-5-thlazolyl	CF3	5Cl
P219	2-chloro-5-th!azolyl	CF3	5F
P220	2-chloro-5-thiazolyl	CF3	4Ci
P221	6-chloro-3-pyridyl	CF3	3Me
P222	6-chloro-3-pyridyl	CF3	4Me
P223	6-chioro-3-pyrldyl	CF3	5Me
P224	phenyl	CF3	H
P225	4-chlorophenyl	CF3	H
P226	3-pyrldyl	CF3	H
P227	6-chloro-5-fluoro-3pyridyf	CF3	H
P228	6-trlfiuoromethyl-3pyrldyl	CF3	H

191 [Table 39-2]

P229	6-fluoro-3-pyridyl	CF3	H
P230	5,6-dichloro-3-pyridyl	CF3	H
P231	6-bromo-3-pyridyi	CF3	H
P232	6-chloro-3-pyridyl	CF3	4F
P233	6-chloro-3-pyridyi	CF3	3F
P234	6-chioro-3-pyridyl	CHCI2	H
P235	6-chioro-3-pyridyl	CCI3	H
P236	6-chioro-3-pyridyl	CH2CI	H
P238	6-chloro-3-pyrldyl	CHF2	H
P239	6-chloro-3-pyridyl	CF2CI	H
P240	6-chloro-3-pyrldyi	CHCIBr	H
P241	6-chloro-3-pyrldyi	CHBr2	H
P242	6-chloro-3-pyridyl	CF2CF3	H
P243	2-chloro-5-pyrimidinyl	CF3	H
P244	6-chloro-3-pyridyl	CH2Br	H

Examples of more preferred compounds include

N-[1-i(6*chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide (Compound P212) and

N-[1-((6-chloropyridln-3-yl)methyl)pyridln-2(1H)-ylidene]-2_l2_l2-trifluoroethanethÎoamide (Compound 1-20), N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoro-N'Isopropylacetimidamide (Compound 1-45).

ln addition, In the présent Invention, an acid addition sait of a novel iminopyridine dérivative represented by Formula (I) (preferably, an agriculturally and zootechnically acceptable acid addition sait) may also be used, and examples thereof Include an acid addition sait such as hydrochloride, nitrate, sulfate, phosphate, or acetate and the like.

The novel iminopyridine dérivative represented by Formula (I) Itself shows excellent pest control effects against pest insects, and is mlxed and used with other pest control agents, thereby showing excellent pest control effects compared to when a single agent is used.

Therefore, the présent invention provides a pest control composition prepared by containing at least one of novel iminopyridine dérivatives represented by Formula (I) and at least one of other pest control agents. Furthermore, the présent invention provides an excellent pest

192 control composition prepared by containing at least one of novel Iminopyridine dérivatives represented by Formula (I) and at least one of other Insecticides and/or fongicides.

Exampies of a pest control composition provided by the présent invention include a pest control agent for agriculturai and hortlcultural, a control agent for animal parasitlc pests. an agent for controlling hyglene pests. an agent for controlling nuisance pests. an agent for controlling stored grain and stored product pests. an agent for controlling house pests and the like, preferred examples thereof Include a pest control agent for agriculturai and horticultural and a control agent for animal parasitic pests.

Examples of the Insect species against which a pest control composition containing a novel iminopyridine dérivative represented by Formula (I) or at least one of acid addition salts thereof, and at least one of other pest control agents shows pest control effects Include lepidopteran pests (for example, Spodoptera litura, cabbage armyworm, Mythimna separata, cabbageworm, cabbage moth, Spodoptera exlgua, rice stem borer, grass leaf relier, tortricîd, codling moth, leafminer moth, tussock moth, Agrotis spp), Helicoverpa spp, Heliothis spp and the like), hemipteran pests (for example, aphids (Aphididae, Adelgidae, Phylloxeridae) such as Myzus persicae, Aphis gossypil, Aphis fabae, com leaf aphid, pea aphld, Aulacorthum solanl, Aphis craccivora, Macrosiphum euphorbiae, Macrosiphum avenae, Methopolophium dirhodum, Rhopalosiphum padi, greenbug, Brevicoryne brassicae, Llpaphis erysiml, Aphis citricola, Rosy apple aphid. apple blight, Toxoptera aurantli andToxoptera citricldus, leafhoppers such as Nephotettlx clncticeps and Empoasca vltis, planthoppers such as Laodelphax striateilus, Nilaparvata lugens and Sogatella forcifera, Pentatomorpha such as Eysarcoris ventralis, Nezara vlridula and Trigonotylus coelestialium, whiteflies (Aleyrodidae) such as sllverfeaf whitefly, Bemisia tabaci and greenhouse whitefly, and scale Insects (Diaspididae, Margarodidae, Ortheziidae, Aclerdiae, Dactylopiidae, Kerridae, Pseudococcidae, Coccldae, Eriococcidae, Asterolecaniidae, Beesonldae, Lecanodiaspididae, Cerococcidae and the like) such as Pseudococcus comstockl, Planococcus citri, Pseudaulacaspis pentagona and Aonldiella aurantii), coleopteran pests (for example, Llssorhoptrus oryzophilus, Callosobruchus

193 chinensis, Tenebrio molitor, Diabrotica vlrgifera virgifera, Diabrotica undecimpunctata howardi, Anomala cuprea, Anomala rufocuprea, Phyllotreta striolata, Aulacophora fe moral is, Leptlnotarsa decemlineata, Ouléma oryzae, Bostrichidae, Cerambycidae and the like), Acarina (for exampie, Tetranychus urticae, Tetranychus kanzawai, Panonychus citri and the like). hymenopteran pests (for example, Tenthredinidae), orthopteran pests (for example, Acridioidea), dipteran pests (for example, Agromyzldae), thysanopteran pests (for exampie, Thrips palmi, Frankiiniella occidentalis and the like), phytoparasltic nematode (for example, Meloidogyne, Pratylenchus, Aphelenchoides besseyi, Bursaphelenchus xytophlius and the like), and the like, examples of zooparasites Include Ixodidae (for example, Amblyomma americanum, Amblyomma maculatum, Boophilus microplus, Dermacentor andersoni, Dermacentor occidentalis, Dermacentor variabilis, Haemaphysalis campanulata, Haemaphysalis flava, Haemaphysalis longicomis, Haemaphysalis megaspinosa Saito, Ixodes nlpponensis, Ixodes ovatus, Ixodes padfcus, Ixodes persulcatus, Ixodes ricinus, Ixodes scapularis, Omithodoros moubata paclfcus and Rhipicephalus sanguineus), Cheyletidae (for example, Cheyletiella blakei and Cheyletiella yasguri), Demodex (for example, Demodex canis and Demodex cati), Psoroptldae (for example, Psoroptes communis), Sarcoptidae (for example, Chorioptes bovis and Otodectes cynotls), Dermanyssidae (for example, Omithonyssus sylviarum), Dermanyssus gallinae, Pterolichus (for example, Megnlnla cubitalls and Pterolichus obtusus), Trombiculidae (for example, Helenlcula miyagawai and Leptotrombidium akamushi), Shiphonaptera (for example, Ctenocephalides felis, Pulex Irritans, Xenopsylla cheopis and Xenopsylla), Mallophaga (for example, Trichodectes canis and Menopon gallinae), Anoplura (for example, Haematoplnus suis, Linognathus setosus, Pediculus humanus humanus, Pediculus humanus, Pthirus pubis and Cimex lectularius), Diptera (for example, Musca domestica, Hypoderma bovis, Stomoxys calcitrans and Gasterophilus), Psychodidae (for example, Phlebotomus), Glossina morsitans, Tabanldae, Ormosia tokionis (for example, Aedes albopictus and Aedes aegyptl), Culicidae (for example, Culex plpiens pallens), Anophelinl, Ceratopogonidae and the like), Slmulildae,

194

Ceratopogonidae, Reduviidae, Monomorium pharaonis, Nematoda (for example, Strongyloides, Ancylostomatoidea, Strongyloidea (for example, Haemonchus contortus and Nippostrongylus braziltensis), Trichostrongyloldea, Metastrongyloidea (for example, Metastrongylus elongatus, Angiostrongylus cantonensis and Aelurostrongylus abstrutus), Oxyuroidea, Haterakoidea (for example, Ascaridia galli), Ascaridoidea (for example, Anisakls simplex, Ascaris suum, Parascaris equorum, Toxocara canis and Toxocara cati), Spiruroidea (for example, Subuluroidea, Gnathostoma spinigerum, Physaloptea praeputialis, Ascarops strongylina, Draschia megastoma and Ascarla hamulosa, Dracunculus medinensls), Fllarioldea (for example, Dtrofîlaria immitis, lymphatic filarial, Onchocerca volvulus and Loa loa), Dioctophymatoidea, Trichlnelia (for example, Trichuris vulpis and Trichineila spiralis), Trematoda (for example, Schistosoma japonicum and Fasciola hepatica), Acanthocephala, Taenia (for example, Pseudophyllidea (for example, Spiromètre erinaceleuropaei) and Cyclophyllidea (for example, Dipylidium canlnum)), Protozoa, and the like, and examples of hygiene pests Include Periplaneta (for example, Blattella germanica), Acaridae (for example, Tyrophagus putrescentiae), and Isoptera (for example, Coptotermes formosanus). Among them, preferred examples of an insect species, to which the pest control agent of the présent invention Is applled, include lepidopteran pests, hemipteran pests, thysanopteran pests, dipteran pests, coleopteran pests, zooparasitic Shiphonaptera or Acari, Dirofilaria immitis, Periplaneta and Isoptera (for example, at least one insect species selected from the group consisting of cabbage moth, Spodoptera litura, Aphls gossypii, Myzus perslcae, Laodelphax striateilus, Nilaparvata lugens, Sogatella furcifera, Nephotettix clncticeps, Frankliniella occidentalis, Aulacophora femoralis, Ouléma oryzae, Lissorhoptrus oryzophilus, Trigonotylus coelestialium, Musca domestica, Haemaphysaiis longicomls, Dirofilaria immitis, Blattella germanica and Coptotermes formosanus), and particulariy preferred examples thereof include cabbage moth, Aphls gossypii, Myzus perslcae, Laodelphax striateilus, Nilaparvata lugens, Sogatella furcifera, Nephotettix cincticeps, Aulacophora femoralis, Ouléma oryzae, Lissorhoptrus oryzophilus, Trigonotylus coelestialium, Musca domestica and Haemaphysaiis

195 longicomis.

In the présent spécification, examples of other pest control agents which may be mixed with the novel Iminopyridine dérivative represented by Formula (I) include an insecticide, a fungicide, a miticide, a herbicide, a plant growth regulator and a control agent for animal parasites, and exampies of a spécifie chemical Include those described in The Pesticide Manual (13th édition and published by the British Crop Protection Council) and the SHiBUYA INDEX (15th édition, 2010 and published by SHIBUYA INDEX RESEARCH GROUP).

Exampies of other pest control agents which may be mixed with the novei iminopyridine dérivative represented by Formula (I) preferably Include an insecticide, a fungicide, a herbicide and a control agent for animal parasitic pests, and also those prepared by mixing a fungicide with an Insecticide.

Preferred examples of other pest control agents which may be mixed with the novel Iminopyridine dérivative represented by Formula (I) include an organic phosphoric ester compound, a carbamate-based compound, a nerelstoxln dérivative, an organochlorine compound, a pyrethroid-based compound, a benzoyl urea-based compound, a juvénile hormone-iike compound, a molting hormone-like compound, a neonicotinold-based compound, a sodium channel blocker for nerve cells, an insecticidalmacrocyclic lactone, a γ-aminobutyric acid (GABA) antagonist, a ryanodine receptor agonistic compound, insecticidal ureas, a BT agent, an entomopathogenic viral agent and the like, as an insecticide, and more preferred examples thereof include an organic phosphoric ester compound such as acephate, dichlorvos, EPN, fenitrothion, fenamifos, prothiofos, profenofos, pyraclofos, chlorpyrifos-m ethyi, diazinon, trichlorfon, tetrachlorvinphos, bromofenofos and cythioate, a carbamate-based compound such as methomyl, thiodicarb, aldicarb, oxamyl, propoxur, carbaryl, fenobucarb, ethiofencarb, fenothiocarb, pirimicarb, carbofuran and benfuracarb, a nereistoxin dérivative such as cartap and thiocyciam, an organochlorine compound such as dicofol and tetradifon, a pyrethroidbased compound such as allethrin, d-d-T allethrin, d!d-T80 allethrin, pyrethrins, phenothrin, flumethrin, cyfluthrin, d-d-T80 prarethrin, phthaithrin, transfluthrin, resmethrin, cyphenothrin,

196 pyrethrum extract, synepirin222, synepirinSOO, permethrin, tefluthrin, cypermethrin, deltamethrin, cyhalothrin, fenvalerate, fluvalinate, ethofenprox and silafluofen, a benzoyl ureabased compound such as diflubenzuron, teflubenzuron, flufenoxuron, chlorfluazuron and lufenuron, a juvénile hormone-like compound such as methoprene and a molting hormone-like compound such as chromafenozide. In addition, examples of other compounds Include buprofezln, hexythlazox, amitraz, chlordimeform, pyridaben, fenpyroxymate, Pyrimldifen, tebufenpyrad, tolfenpyrad, acequlnocyl, cyflumetofen, flubendizmlde, ethlprole, fîpronil, etoxazole, imldacloprid, clothlanldin, thlamethoxam, acetamiprid, nitenpyram, thlacloprid, dinotefuran, pymetrozine, bifenazate, spirodiclofen, spiromeslfen, spirotetramat, flonicamid, chlorfenapyr, pyriproxyfen, Indoxacarb, pyridalyi, spînosad, splnetoram, avermectin, milbemycin, pyflubumide, cyenopyrafen, pyrifluqulnazon, chlorantraniliprole, cyantraniliprole, lepimectin, metaflumizone, pyrafluprole, pyriprole, hydramethylnon, triazamate, sulfoxaflor, flupyradifurone, flometoquin, ivermectin, selamectin, moxidectin, doramectin, eprinomectin, milbemycin oxime, deet, metoxadiazon, cyromazine, triflumuron, star anlse oil, triclabendazole, flubendazole, fenbendazole, antimony sodium gluconate, levamisole hydrochloride, bithionol, dlchlorofen, phenothiazine, piperazine carbon bisulfide, piperazine phosphate, piperazine adipate, piperazine citrate, melarsomine dihydrochloride, metyridine, santonin, pyrantel pamoate, pyrantel, praziquantel, febantel, emodepside, emamectin benzoate, cycloxaprid, 1((6-chloropyridln-3-yl)methyl)-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrlmldln-1-lum-2-olate, an organic metal-based compound, a dinitro-based compound, an organic sulfur compound, a urea-based compound, a triazine-based compound, a hydrazine-based compound, and a compound represented by the following Formula (II) or agriculturally and zootechnlcally acceptable acid addition salts thereof. Examples of those acid addition salts Include hydrochloride, nitrate, sulfate, phosphate, or acetate and the like.

[Chemical Formula 42]

197

[in the formula, Het1 represents a 3-pyridyl group,

R1 represents a hydroxyl group,

R2 and R3 represent a cyclopropylcarbonyloxy group, and

R4 represents a hydroxyl group]

More preferred examples of other insecticides which may be mixed with the novel imlnopyridine dérivative represented by Formula (i) include acetamiprid, Imidacloprid, nitenpyram, clothianidin, acetamiprid, dinotefuran, thlacloprid, thlamethoxam, pymetrozine, splnosad, spinetram, fipronil, chioranthraniliprole, cyantraniliprole), cartap, thiocyclam, benfuracarb, buprofezin, ethofenprox, silafluofen, ethiprole, flonicamid, sulfoxaflor, flupyradifurone, flometoquin, emamectin benzoate, cycloxaprid, 1-((6-chloropyridin-3yt)methyl)-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimldin-1-lum-2-olate, afidopyropen, and the compound represented by Formula (II), or agriculturally and zootechnically acceptable acid addition salts thereof, and particulariy preferred examples thereof Include permethrin, acetamiprid, Imidacloprid, clothianidin, dinotefuran, thlacloprid, thlamethoxam, pymetrozine, spinosad, spinetram, fipronil, chioranthraniliprole, cyantraniliprole, amitraz, ethofenprox, silafluofen, ethiprole, flonicamid, sulfoxaflor, flupyradifurone, flometoquin, ivermectîn, moxidectin, emamectin benzoate, cycloxaprid, 1-((6-chloropyridin-3-yl)methyl)-4-oxo-3-phenyl4H-pyrido[1,2-a]pyrimidln-1-lum-2-olate, and afidopyropen, or agriculturally and zootechnically acceptable acid addition salts thereof.

The novel Imlnopyridine dérivative represented by Formula (i) may be used together or

198 in combination with a microbial pesticide such as a BT agent and an entomopathogenic viral agent.

Examples of the fungicide which may be mixed with the novel iminopyridine dérivative represented by Formula (I) include, for example, a strobilurin-based compound such as azoxystrobin, orysastrobin, kresoxym-methyl and trifloxystrobin, an anilinopyrimidine-based compound such as mepanipyrim, pyrimethanil and cyprodinil, an azole-based compound such as triadimefon, bitertanol, triflumlzole, etaconazole, propic onazole, penconazole, flusilazole, myclobutanil, cyproconazole, tebuconazole, hexaconazole, prochloraz and simec onazole, a quinoxaline-based compound such as quinomethionate, a dithiocarbamate-based compound such as maneb, zineb, mancozeb, polycarbamate and propineb, a phenyl carbamate-based compound such as diethofencarb, an organochlorine compound such as chlorothalonil and qulntozene, a benzimldazole-based compound such as benomyl, thiophanate-methyl and carbendazole, a phenyl amide-based compound such as metalaxyl, oxadixyl, ofurase, benalaxyl, furalaxyl and cyprofuram, a sulfenlc acid-based compound such as dichlofluanid, a copper-based compound such as copper hydroxide and copper oxyquinoline (oxine-copper), an isoxazole-based compound such as hydroxyisoxazole, an organic phosphorus-based compound such as fosetyl-aluminium and tolclofos-methyl, an N-halogenothioalkyl-based compound such as captan, captafol and folpet, a dicarboximide-based compound such as procymidone, iprodione and vinchlozolin, a benzanilide-based compound such as thlfluzamlde, furametpyr, flutolanil and mepronil, a morpholine-based compound such as fenpropimorph and dimethomorph, an organic tin-based compound such as fenthin hydroxide and fenthin acetate, a cyanopyrrole-based compound such as fludioxonil and fenpiclonil, 9-membered cyclic dilactone compounds such as acibenzolar-S-methyl, Isotianil, tladinil, carpropamid, diclocymet, fenoxanil, tricyclazole, pyroquilon, ferimzone, fthalide, fluazinam, cymoxanil, triforine, pyrifenox, probenazole, fenarimol, fenpropidtn, pencycuron, cyazofamid, iprovalicarb, tebufloquin, benthiavalicarb-lsopropyl, tolprocarb, validamycin, Kasugamycin, Streptomycin and UK-2As, a compound represented by the following Formula (III), which is described In JP-A No. 2009·

199

078991, a compound represented by the following Formula (IV), which Is described in Republication No. W008/066148, and a compound represented by the following Formula (V), which Is described in Republication No. W009/028280, or agriculturally and zootechnicaliy acceptable acid addition salts thereof.

[Chemical Formula 43] [in the formula, R1 and R2 represent a hydrogen atom or a haloalkyl group having 1 to 6 carbon atoms and the like (however, at least one of R1 and R2 represents a haloalkyl group having 1 to 6 carbon atoms), R3 represents a hydrogen atom and the like, A represents OR4, SR5, NR6R7 or NR8NR9R10, R4 represents an alkyl group having 8 to 12 carbon atoms and the like, R5 represents an alkyl group having 1 to 12 carbon atoms and the like, R6 and R7 represent a hydrogen atom or an alkyl group having 8 to 12 carbon atoms, and R8, R9 and R10 represent a hydrogen atom or an alkyl group having 1 to 12 carbon atoms and the like] [Chemical Formula 44] [in the formula, R1 and R2 represent a C1 to C6 alkyl group, an aryl group, a heteroaryl group, or a aralkyl group,

R3 and R4 represent a hydrogen atom, a C1 to C6 alkyl group, a halogen atom, or a C1 to C6 alkoxy group,

X represents a hydrogen atom, a halogen atom, a C1 to C6 alkyl group, a C2 to C6 alkenyl group, a C2 to C6 alkynyl group, an aryl group, a heteroaryl group, or a C1 to C6 alkoxy group,

200

Y represents a hydrogen atom , a halogen atom, a C1 to C6 alkyl group, or a C1 to C6 alkoxy group, and n represents 0 to 4, and m represents 0 to 6 ] [Chemical Formula 45]

(V) [in the formula, R1 represents an alkyl group and the like, R2 and R3 each Independently represent a hydrogen atom, a haloalkyl group and the like (however, at least one of R2 and R3 Is a haloalkyl group having 1 to 6 carbon atoms), A represents -OR4, -SR5, NR6R7 or -NR8NR9R10, R4 represents an alkyl group having 3 to 12 carbon atoms, R5 represents an alkyl group having 1 to 12 carbon atoms, R6 represents a hydrogen atom, R7 represents an alkyl group having 5 to 12 carbon atoms, and R8, R9 and R10 each represent an alkyl group having 3 to 12 carbon atoms and the like, an alkyl group having 1 to 12 carbon atoms and the like, a hydrogen atom and the like, an alkyl group having 5 to 12 carbon atoms and the like, and an alkyl group having 1 to 12 carbon atoms, respectively.]

More preferred examples of other fongicides which may be mlxed with the novel Imlnopyridine dérivative represented by Formula (I) Include azoxystrobln, orysastrobin, thifluzamlde, furametpyr, fthalide, probenazole, acibenzolar-S-methyl, tiadinil, Isotianil, carpropamld, diclocymet, fenoxanil, tricyclazole, pyroquilon, ferimzone, tebufloquin, slmeconazole, validamycin, kasugamycln and pencycuron, and particulariy preferred examples thereof include probenazole and tebufloquin.

Preferred examples of other pest control agents which may be mlxed with the novel iminopyridine dérivatives represented by Formula (I) also include herbicides such as llpld synthesîs Inhibitors, acetolactate synthesîs inhibitors, photosystem inhibitors, protoporphyrinogen IX oxldatlon inhibitors, bleacher herbicides, amino acid synthesîs Inhibitors, dlhydropteroate synthetase

201

Inhibitors, cell division inhibitors, very-long-chaln fatty acid synthesis Inhibitors, ceiluiose blosynthesls inhibitors, decoupllng agents, auxln-like herbicides, auxin transport Inhibitors, and the like. Spécifie examples here are alloxydim, alloxydlm-sodlum, butroxydlm, clethodlm, clodlnafop, ciodinafop-propargyl, cycloxydlm, cyhaiofop, cyhalofop-butyl, dlclofop, dlclofop-methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fiuazifop, fluazifop-butyl, fluazifop-P, fluazifop’P-butyi, haloxyfop, haioxyfop-P-methyi, haloxyfop-P, haloxyfop-P-methyl ester, metamlfop, plnoxaden, profoxydim, propaqulzafop, quizalofop, quizalofop-ethyl, quizalofop-tefuryl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, sethoxydim, tepraloxydim, tralkoxydim, benfuresate, butyiate, cycioate, daiapon, dimepiperate, ethyi dlpropylthiocarbamat (EPTC), esprocarb, ethofumesate, flupropanate, mollnate, orbencarb, pebulate, prosuifocarb, trichloroacetic acid (TCA), thlobencarb, tiocarbazii, trlallate, vernolate, suifonylureas (amidosulfuron, azlmsuifuron, bensulfuron, bensulfuron-methyl, chlorimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosuifamuron, ethametsulfuron, ethametsulfuron-methyl, ethoxysuifuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazosulfuron, iodosulfuron, iodosulfuron-methyl sodium, mesosulfuron, metazosulfuron, metsulfuron, metsuifuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron, prlmisulfuron-methyl, propyrlsulfuron, prosulfuron, pyrazosuifuron, pyrazosulfuron-ethyl, rimsulfuron, suifometuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron, thlfensulfuron-methyl, trlasuifuron, tribenuron, tribenuron-methyi, trlfloxysulfuron, triflusulfuron, trlflusulfuron-methyl, and tritosulfuron), Imazamethabenz, Imazamethabenz-methyi, imazamox, Imazaplc, Imazapyr, Imazaquln, imazethapyr, triazolopyrlmidine herbicides (chloransulam, cioransulam-methyl, diclosulam, flumetsulam, florasulam, metosulam,

202 penoxsulam, pyrimisulfan, and pyroxsulam), bispyribac, bispyribac-sodium, pyribenzoxim, pyriftalid, pyriminobac, pyrlminobac-methyl, pyrithlobac, pyrithiobac-sodium, flucarbazone, flucarbazone-sodium, propoxycarbazon, propoxycarbazon-sodium, thiencarbazone, thiencarbazone-methyl, triazine herbicides (chlorotriazine, triazinones, triazindiones, methylthiotrlazines, and pyrldazlnones (for example, ametryn, atrazine, chlorldazone, cyanazine, desmetryn, dimethametryn, hexazlnone, metrlbuzln, prometon, prometryn, propazlne, slmazin, simetryn, terbumeton, terbuthylazln, terbutryn, and trietazin)), arylureas (for example, chlorobromuron, chlorotoluron, chloroxuron, dimefuron, dluron, fluometuron, isoproturon, isouron, linuron, metamltron, methabenzthlazuron, metobenzuron, metoxuron, monolinuron, neburon, siduron, tebuthluron, and thladiazuron), phenylcarbamate esters (for example, desmedlpham, karbutilat, phenmedipham, and phenmedlpham-ethyl), nltrlle herbicides (for example, bromofenoxim, bromoxynil and its salts and esters, and ioxynil and Its salts and esters), uraclls (for example, bromacll, lenacll, and terbacll), bentazon, bentazon-sodium, pyrldate, pyrldafol, pentanochlor, propanll, inhibitors of the photosystem (such as diquat, diquat-dlbromlde, paraquat, paraquatdichloride, and paraquat dlmethyl sulfate), acifluorfen, acifluorfen-sodlum, azafenidin, bencarbazone, benzfendlzone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, cinldon-ethyl, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumloxazln, fluoroglycofen, fluoroglycofen-ethyl, fluthlacet, fluthlacet-methyl, fomesafen, halosafen, lactofen, oxadlargyl, ozadlazon, oxyfluorfen, pentoxazone, profluazol, pyraclonll, pyraflufen, pyraflufen-ethyl, safiufenacil, sulfentrazone, thidiazimin, beflubutamid, diflufenlcan, flurldone, flurochloridone, flurtamone, norflurazon, pyrazolate, plcollnafen, aclonlfen, amitrole, clomazone, flumeturon, glyphosate and Its salts, blalaphos, bialaphos-sodium, glufoslnate, glufosinate-P,

203 glufoslnate-ammonium, asulam, dinltroanilines (for example, benfluralln, butralin, dlnitramine, ethaIfluralln, fluchioralin, oryzalin, pendimethalln, prodiamine, and trlfluralin), phosphoramidate herbicides (for example, amiprophos, amiprophos-methyi, and butamifos), benzoic acid herbicides (for example, chlorthal and chlorthal-dimethyl), pyridlnes (for example, dlthiopyr and thiazopyr), benzamldes (for example, propyzamide and tebutam), chioroacetamldes (for example, acetochlor, alachlor, butachior, dlmethachlor, dimethenamld, dimethenamld-P, metazachlor, metoiachlor, metolachlor-S, pethoxamide, pretllachlor, propachlor, proplsochior, and thenylchlor), oxyacetanllldes (for example, flufenacet and mefenacet), acetanllides (for example, diphenamlde, naproanllide, and napropamide), tetrazollnones (for example, fentrazamlde), anilofos, cafenstrole, fenoxasuifone, Ipfencarbazone, piperophos, pyroxasuifone, chiorthiamid, dlchlobenll, flupoxam, isoxaben, dlnoseb, dlnoterb, 4,6-dinitro-o-cresol (DNOC) and Its salts, 2,4-D and Its salts and esters, 2,4-B and Its salts and esters, aminopyralld and Its salts (for example, amlnopyra1ld-trls(2-hydroxypropyl)ammonium) and esters, benazolln, benazolln-ethyl, chloramben and its saits and esters, clomeprop, clopyralld and Its salts and esters, dicamba and Its salts and esters, dlchlorprop and Its salts and esters, dichlorprop-P and Its salts and esters, fluroxypyr and Its salts and esters, 2-methyl-4-chlorophenoxyacetlc acid (MCPA) and Its salts and esters, MCPA-thloethyl, 4-(2-methyl-4-chlorophenoxy)butyric acid (MCPB) and Its salts and esters, mecoprop and its salts and esters, mecoprop-P and Its salts and esters, picloram and its saits and esters, quinclorac, quinmerac, 2,3,6trlchlorobenzolc acid (TBA (2,3,6)) and Its salts and esters, triclopyr and Its salts and esters, amlnocyclopyrachlor and Its salts and esters, diflufenzopyr and Its salts, naptalam and Its salts, bromobutlde, chlorflurenol, chlorfiurenoimethyi, clnmethylin, cumyluron, daiapon, dazomet, dlfenzoquat, dlfenzoquat

204 methyl sulfate, dimethlpln, disodlum methanearsonate (DSMA), dymron, endothal and Its salts, etobenzanid, flamprop, fiamprop-isopropyi, flampropmethyl, flamprop-M-lsopropyl, flamprop-M-methyl, flurenol, fiurenol-butyl, flurprlmidol, fosamine, fosamine-ammonlum, indanofan, indaziflam, maleic hydrazide, mefiuldlde, metam, methlozolln, methyl azlde, methyl bromlde, methyl-dymron, methyl lodide, MSMA, oleic acid, oxaziciomefone, pelargonlc acid, pyrlbutlcarb, quinociamlne, triazlflam, tridiphane, and 6-chloro-3-(2cyclopropyl-6-methyiphenoxy)-4-pyridazinol (CAS 499223-49-3) and Its salts and esters.

Control agents for animal parasitic pests which may be mixed with the novel Iminopyridine dérivatives represented by Formula (I) can be exemplifled by organophosphate ester compounds, carbamate-based compounds, nerelstoxln dérivatives, organochlorine compounds, pyrethroid-based compounds, benzoyl urea-based compounds, juvénile hormone-like compounds, moiting hormone-like compounds, neonicotlnold-based compounds, sodium channel blockers for nerve cells, Insectlcldal macrocyclic lactones, γamlnobutyric acid (GABA) antagonists, ryanodine receptor agonlstlc compounds, insecticidal ureas, and the like. More preferred spécifie examples inciude organophosphate esters such as dlchlorvos, EPN, fenltrothlon, fenamlfos, prothiofos, profenofos, pyraclofos, chlorpyrifos-methyi, diazinon, trichlorfon, tetrachlorvinphos, bromofenofos, cythioate, and fenthion; carbamate-based compounds such as methomyl, thiodlcarb, aidicarb, oxamyi, propoxur, carbaryl, fenobucarb, ethiofencarb, fenothiocarb, pirimicarb, carbofuran, and benfuracarb; nereistoxin dérivatives such as cartap and thiocyciam; organochlorine compounds such as dlcofoi and tetradlfon; pyrethroid-based compounds such as allethrin, d-d-T allethrin, dl-d-T80 allethrin, pyrethrins, phenothrln, flumethrin, cyfiuthrin, d-d-T80 prarethrln, phthalthrln, transfluthrln,

205 resmethrin, cyphenothrin, pyrethrum extract, syneplrln 222, synepirln 500, permethrln, tefluthrln, cypermethrln, deltamethrln, cyhalothrin, fenvalerate, fluvalinate, ethofenprox, and sllafluofen; benzoyl urea-based compounds such as diflubenzuron, teflubenzuron, flufenoxuron, chlorfluazuron, and lufenuron; juvénile hormone-iike compounds such as methoprene; molting hormone-llke compounds such as chromafenozide; and other compounds such as amitraz, chlordimeform, fipronil, etoxazole, Imldacloprid, clothlanldln, thiamethoxam, acetamiprid, nitenpyram, thiacloprid, dinotefuran, spirodiclofen, pyriproxyfen, Indoxacarb, splnosad, spinetoram, avermectln, mllbemycin, metaflumlzone, pyrafluprole, pyriprole, hydramethylnon, triazamate, sulfoxaflor, flupyradlfurone, Ivermectln, selamectln, moxidectln, doramectln, eprlnomectin, mllbemycin oxlm, dlethylcarbamazine citrate, deet, metoxadiazon, cyromazlne, triflumuron, star anlse oll, triclabendazole, flubendazole, fenbendazole, antimony sodium gluconate, levamisole hydrochloride, blthlonol, dlchlorofen, phenothiazlne, piperazine carbon blsulfide, piperazlne phosphate, piperazlne adlpate, plperazlne citrate, melarsomine dihydrochloride, metyridlne, santonin, pyrantel pamoate, pyrantel, praziquantel, febantel, emodepslde, derquantel, monopantel, emamectln benzoate, cycloxaprld, and a compound represented by the following Formula (VI) or agriculturally and zootechnlcally acceptable acid addition salts thereof. Examples of those acid addition salts Include hydrochloride, nitrate, sulfate, phosphate, or acetate and the like.

More preferred examples are fiumethrln, permethrln, fipronyl, pyrlprol, imldacloprid, thiamethoxam, acetamiprld, dinotefuran, amitraz, metafiumizon, pyriproxyfen, fenltrothion, lufenuron, ethoxazoi, splnosad, spinetoram, emodepslde, emamectln benzoate, Ivermectln, selamectln, moxidectln, doramectln, eprlnomectin, derquantel, and monopantel.

Particularly preferred examples Include amitraz and the like.

206

When the pest control composition is a pest control agent for agrlcultural and horticultural, particularly preferred examples for the présent Invention are pest control compositions In which the novel imlnopyrldlne derivatlve represented by Formula (I) is at least one compound selected from N-[1-((6chloropyridin-3-yl)methyl)pyridin-2(1H)-ylldene]-2,2,2-trifluoroacetamlde (Compound P212), N-[1-((6-chioropyrldln-3-yl)methyl)pyrldln-2(1H)-ylldene]2,2,2-trifiuoroethanethioamlde (compound 1*20), or N-[1-((6-chloropyrldin-3yl)methyl)pyridin-2(1H)-ylldene]-2,2,2-trlfluoro-N'-lsopropylacetimidamlde (compound 1*45), and the other pest control agent includes at least one Insecticide or fungiclde selected from acetamiprid, imidacioprid, clothlanidln, dlnotefuran, thiacloprld, fipronil, thlamethoxam, pymetrozlne, flonlcamld, spinosad, cyantraniliprole, chloranthraniliprole, ethofenprox, sllafiuofen, ethiprole, sulfoxaflor, flupyradlfurone, flometoquin, emamectin benzoate, cycloxaprld, 1-((6-chloropyrldln-3-yl)methyl)-4-oxo-3-phenyi-4H-pyrido[1,2a]pyrlmidln-1-lum*2*olate, and afidopyropen, orysastrobin, thifluzamlde, furametpyr, fthalide, probenazole, acIbenzolar-S-methyl, tladlnil, isotianil, carpropamld, diclocymet, fenoxanil, tricyclazole, pyroquilon, ferimzone, tebufloquln, azoxystrobln, simeconazole, validamycin, thifluzamlde, furametpyr, and pencycuron,

The pest control composition of the présent Invention may be prepared using the novel imlnopyrldlne derivatlve represented by Formula (I), other insecticides, fungicldes, herbicides, or control agents for animal parasites, and an agrlculturally and zootechnlcally acceptable carrier (solid carrier, liquid carrier, gaseous carrier, surfactant, dispersant, and other préparation adjuvants).

(Spécifie examples of pesticide préparations)

When the pest control composition of the présent invention is a pest control agent for

207 agricultural and horticultural, the composition is usually mixed with an agriculturally and horticulturally acceptable carrier (solid carrier, liquid carrier, gaseous carrier, surfactant, dispersant and other adjuvants for préparation to be provided In any formulation form of emulsifiable concentrâtes, liquid formulations, suspensions, wettable powders, flowables, dust, granules, tablets, oils, aérosols, fumlgants and the like.

Examples of the solid carrier Include talc, bentonite, clay, kaolin, diatomaceous earth, vermiculite, white carbon, calcium carbonate and the like.

Examples of the liquid carrier Include alcohols such as methanol, π-hexanol and ethylene glycol, ketones such as acetone, methyl ethyl ketone and cyclohexanone, aliphatic hydrocarbons such as n-hexane, kerosene and lamp oil, aromatlc hydrocarbons such as toluene, xylene and methyl naphthalene, ethers such as diethyl ether, dioxane and tetrahydrofuran, esters such as ethyl acetate, nitrites such as acetonitrile and isobutyl nltrile, acid amides such as dlmethylformamide and dimethylacetamide, vegetable oils such as soybean oil and cottonseed oil, dimethyl sulfoxide, water and the like.

Further, examples of the gaseous carrier Include LPG, air, nitrogen, carbonic acid gas, dimethyl ether and the like.

As the surfactant or dispersant for émulsification, dispersion, spreadlng and the like, It ls possible to use, for example, alkylsulfate esters, alkyl (aryl) sulfonates, polyoxyalkylene alkyl (aryl) ethers, polyhydricalcohol esters, lignin sulfonates or the like.

In addition, as the adjuvant for Improving the properties of the préparation, it ls possible to use, for example, carboxymethylcellulose, gum arabic, polyethylene glycol, calcium stéarate or the like.

The aforementioned solid carriers, liquid carriers, gaseous carriers, surfactants, dispersants and adjuvants may be used either alone or in combination, if necessary.

The content of active ingrédients in the préparation is not particulariy limited, but is usually In the range of 1 to 75% by weight for the emulsifiable concentrate, 0.3 to 25% by weight for the dust, 1 to 90% by weight for the wettable powder, and 0.5 to 10% by weight for

208 the granular formulation.

The nove! Iminopyridine dérivatives represented by Formula (I), a préparation Including the same and a mixed formulation of other pest control agents with the same may be applied to pest Insects, plants, plant propagation materials (for example, seeds, plant leaves and stems, roots, soii, water surface and materials for cultivation), rooms which require disturbing the Invasion of pests and the like. The application thereof may be performed before and after the Invasion of pests.

A pest control agent including at least one of the nove! Iminopyridine dérivatives represented by Formula (I) may also be applied to genetlcally-modified crops.

In a preferred aspect thereof, examples of a pest control composition further induding an agriculturally and horticuituraily acceptable carrier Include:

(1 ) a wettable powder composition containing 0.1 to 80% by weight of the novel Iminopyridine dérivative represented by Formula (I), 0.1 to 80% by weight of an Insectldde as another pest control agent, 0.6 to 30% by weight of a wetting agent and a dispersant, and 20 to 95% by weight of an extender, (2) a water dispersibie granule composition containing 0.1 to 80% by weight of the novel iminopyridine dérivative represented by Formula (I), 0.1 to 80% by weight of an Insecticide as another pest control agent, 0.6 to 30% by weight of a wetting agent, a dispersant and a binder, and 20 to 95% by weight of an extender, (3) a flowabie composition containing 0.1 to 80% by weight of the novel iminopyridine dérivative represented by Formula (I), 0.1 to 80% by weight of an insecticide as another pest control agent, 5 to 40% by weight of a dispersant, a thickener, an antifreeze, an antiseptie and an antifoamlng agent, and 20 to 94% by weight of water, (4) an emuisifiabie concentrate composition containing 0.1 to 80% by weight of the novel Iminopyridine dérivative represented by Formula (I), 0.1 to 80% by weight of an Insecticide as another pest control agent, 1 to 30% by weight of an emulsifler and an émulsion stabilizer, and 20 to 97% by weight of an organic solvent,

209 (5) a dust composition containing 0.1 to 80% by weight of the novel iminopyridine dérivative represented by Formula (I), 0.1 to 80% by weight of an insecticide as another pest control agent, and 70 to 99.8% by weight of an extender, (6) a low drift dust composition containing 0.1 to 80% by weight of the novel iminopyridine dérivative represented by Formula (I), 0.1 to 80% by weight of an insecticide as another pest control agent, and 70 to 99.8% by weight of an extender, (7) a microgranule fine composition containing 0.1 to 80% by weight of the novel iminopyridine dérivative represented by Formula (I), 0.1 to 80% by weight of an insecticide as another pest control agent, 0.2 to 10% by weight of a solvent or binder, and 70 to 99.6% by weight of an extender, (8) a granule composition containing 0.1 to 80% by weight of the novel iminopyridine dérivative represented by Formula (i), 0.1 to 80% by weight of an Insecticide as another pest control agent, 0.5 to 30% by weight of a granulation auxiliary (surfactant) and a binder, and 20 to 98% by weight of an extender, and (9) a microcapsule composition containing 0.1 to 80% by weight of the novel Iminopyridine dérivative represented by Formula (I), 0.1 to 80% by weight of an Insecticide as another pest control agent, 1 to 50% by weight of a covering agent, an emulsifier, a dispersant and an antiseptie, and 20 to 98% by weight of water. Preferably, examples thereof Include compositions of (2), (3), (6) and (8).

(Spécifie examples of formulations for animais)

When the pest control agent of the présent invention is a control agent for animal parasitic pests, the agent ls provided in the form of liquid formulations, emulsifiable concentrâtes, liquid drops, sprays, foam préparations, granules, fine granules, dust, capsules, pills, tablets, chewable formulations, injections, suppositories, creams, shampoos, rinses, resin agents, fumigants, poison baits and the like, and is particularly preferably provided in the form of liquid formulations and liquid drops. These forms can be prepared using the following pharmaceutically acceptable carriers.

210

The liquid formulation may also be blended with a typical adjuvant for préparation, such as an emulslfier, a dispersant, a spreadlng agent, a wetting agent, a suspending agent, a preservative and a propellant, and may also be blended with a typical film former. As the surfactant for émulsification, dispersion, spreading and the like, it is possible to use, for example, soaps, polyoxyalkylene alkyl (aryl) ethers, polyoxyethylene alkyl aryl ethers, polyoxyethylene fatty acid ester, higher alcohols, alkyl aryl sulfonates and the like. Examples of dispersants Include caseln, gelatin, polysaccharides, lîgnin dérivatives, saccharides, synthetic water soluble polymers and the like. Examples of spreading wetting agents Include glycerin, polyethylene glycol and the like. Examples of suspending agents Include casein, gelatin, hydroxypropylcellulose, gum arable and the like, and examples ofstabllizers Include phenolic antloxidants (BHT, BHA and the like), amine antloxldants (diphenylamine and the like), organic sulfur antioxidants and the like. Examples of preservatives include methyl poxybenzoate, ethyl p-oxybenzoate, propyl p-oxybenzoate, butyl p-oxybenzoate and the like. The aforementioned carriers, surfactants, dispersants and adjuvants may be used either alone or in combination, If necessary. Furthermore, perfumes, synergists and the like may also be incorporated. The suitable content of the active Ingrédients In the pest control agent of the présent Invention Is usually 1 to 75% by weight for the liquid formulation.

Examples of carriers used for the préparation of creams include non-volatile hydrocarbons (liquid paraffin and the like), lanolin hydrogenated fats and oils, higher fatty acids, fatty acid esters, animal and vegetable oils, silicone oils, water and the like. Further, emulsifiers, humectants, antioxidants, perfumes, borax and ultraviolet absorbera may also be used either alone or in combination, if necessary. Examples of emulsifiers include fatty acid sorbitan, polyoxyethylene alkyl ethers, and fatty acid polyoxyethylene and the like. The suitable content of the active ingrédients in the pest control agent of the présent invention Is usually 0.5 to 75% by weight for the cream.

The capsules, pills or tablets may be used such that the active ingrédients ln the composition of the présent invention are mixed with a carrier such as starch, lactose or talc, a

211 dlsintegrator and/or a binder, such as magnésium stéarate is added thereto, and, if necessary, the mixture is tabieted.

Carriers for the préparation of injections need to be prepared as an aseptie solution, but the solution may contain other substances, for example, a sait or glucose enough to isotonicate the solution with blood. As available carriers, injections need to be prepared as an aseptie solution. For injections, the solution may contain, for example, a sait or glucose enough to isotonicate the solution with blood. Examples of available carriers for the préparation of Injections Include esters such as fatty acid dérivatives of glyceride, benzy! benzoate, Isopropyl myristate and propylene gtycoi, and organic solvents such as Nmethylpyrrolidone and glycerol formai. The content of the active ingrédients in the pest control agent of the présent Invention is usually 0.01 to 10% by weight for the Injection.

Examples of carriers for the préparation of resin agents Include vinyl chloride polymers, polyuréthane and the like. Plasticlzers such as phthalic acid esters, adipic acid esters and stearic acid may be added to these bases, If necessary. After the active ingrédients are kneaded into the base, the kneaded product may be molded by Injection molding, extrusion molding, press molding and the like. In addition, the molded product may also be properly subjected to processes such as molding or cutting to form an ear tag for animais or insecticldal collar for animais.

Examples of carriers for toxic baits Include bait substances and attraction substances (farina such as wheat flour and corn flour, starch such as corn starch and potato starch, saccharides such as granulated sugar, malt sugar and honey, food flavors such as glycerin, onlon flavor and milk flavor, animal powders such as pupal powder and fish powder, various pheromones and the like). The suitable content of the active ingrédients in the pest control agent of the présent invention Is usually 0.0001 to 90% by weight for the toxic bait.

The pest control composition according to the présent invention may be used such that a préparation form prepared by Independently induding at least one of the novel Iminopyridine dérivative represented by Formula (I) as the active ingrédient in the composition, or acid

212 addition salts thereof and at least one of other pest control agents alone Is formulated and these Ingrédients when used are mixed on the spot.

Therefore, according to another aspect of the présent invention, there is provided a combined product prepared by Inciuding at least one of the novel Iminopyridine dérivative represented by Formula (I) as the active ingrédient or acid addition salts thereof and at least one of other pest control agents.

According to another preferred aspect of the présent Invention, In the combined product, the novel iminopyridine dérivative represented by Formula (I) or acid addition salts thereof Is provided as a first composition prepared by inciuding the same as active ingrédients, and other pest control agents is provided as a second composition prepared by inciuding the same as active ingrédients. In this case, the first composition and the second composition may be any formulation form which uses appropriate carriers or adjuvants in combination thereof in the same manner as in the case of the aforementioned pest control composition. The combined product may be provided In the form of a pharmaceutical set.

According to still another aspect of the présent invention, there is provided a method for protecting useful plants or animais from pests, Inciuding: simultaneously or independently (preferably, each ingrédient simultaneously) applying at least one of the novel Iminopyridine dérivative represented by Formula (I), enantiomers thereof, mixtures thereof or acid addition salts thereof as an active ingrédient and at least one of other pest control agents to a région to be treated.

In the method, simultaneously applying also includes mixing at least one of the novel iminopyridine dérivative represented by Formula (I) or acid addition salts thereof and at least one of other pest control agents before being applied to a région to be treated, and applying the mixture thereto. Independently applying includes, without mixing these ingrédients in advance, applying the novel iminopyridine dérivative represented by Formula (I) or acid addition salts thereof eariier than the other ingrédients, or applying the novel iminopyridine dérivative represented by Formula (I) or acid addition salts thereof later than the other

213 ingrédients.

According to still another preferred aspect of the présent Invention, there is provided a method for protecting useful plants or animais from pests, Including: applying (1) a first composition prepared by Including at least one of the novel Iminopyridine dérivative represented by Formula (I) or acid addition salts thereof as an active Ingrédient, and (2) a second composition prepared by Including at least one of other pest control agents as an active Ingrédient to a région to be treated.

According to yet another aspect of the présent Invention, there Is provided a method for protecting useful plants from pests, Including: applying the composition or combined product of the présent invention as It Is or diluted to pests, useful plants, seeds of useful plants, soil, cultivation carriers or animais as a target, and preferably to useful plants, soil or animais.

According to still yet another aspect of the présent Invention, there is provided a use of the composition or combined product of the présent Invention in order to protect useful plants or animais from pests.

Furthermore, preferred examples of the method for applying the composition or combined product of the présent invention to pests, useful plants, seeds of useful plants, soil or cultivation carriers as a target include spray treatment, watar surface treatment, soil treatment (mixing, irrigation and the like), nursery box treatment, surface treatment (application, dust coating and covering) or fumigation treatment (treatment in enclosed space, such as covering soi! with a polyfilm after soil injection) and the like, and more preferred examples Include water surface treatment, soil treatment, nursery box treatment or surface treatment.

The throughput in the case of application to plants by spray treatment Is 0.1 g to 10 kg per 10 ares of cultlvated land and preferably 1 g to 1 kg, as an amount of active Ingrédients of the composition of the présent invention.

Further, exampies of a method for treating seeds, roots, tubers, bulbs or rhizomes of

214 plants Include a dîpping method, a dust coatlng method, a smearing method, a spraying method, a pelleting method, a coating method and a fumlgatlng method for the seed. The dipplng method Is a method In which seeds are dlpped In a liquid chemical solution, and the dust coatlng method Is classified Into a dry dust coating method In which a granular chemical Is adhered onto dry seeds, and a wet dust coating method In which a powdery chemical Is adhered onto seeds which hâve been slightly soaked In water. In addition, the smearing method Is a method In which a suspended chemical Is applied on the surface of seeds within a mixer and the spraying method Is a method In which a suspended chemical Is sprayed onto the surface of seeds. Furthermore, the pelleting method Is a method In which a chemical Is mlxed with a filler and treated when seeds are pelleted together with the filler to form pellets having certain size and shape, the coating method Is a method In which a chemical-containing film Is coated onto seeds, and the fumigating method Is a method In which seeds are sterilized with a chemical which has been gaslfied within a hermetically sealed container.

Examples of the preferred treatment method of the composition of the present invention Include a dipplng method, a dust coating method, a smearing method, a spraying method, a pelleting method and a coating method.

Further, the composition of the present invention may also be used to, In addition to seeds, germinated plants which are transplanted after germination or after budding from soil, and embryo plants. These plants may be protected by the treatment of the whole or a part thereof by dipplng before transplantation.

The throughput in the case of application to seeds of plants Is not particulariy limited, but preferably 1 g to 10 kg and more preferably 100 g to 1 kg per 100 kg of seeds, as an amount of active Ingrédients of the composition of the present Invention.

In addition, the method for application of the composition of the present Invention to soil Is not particulariy limited, but preferred application methods are as follows.

Examples of the method Include a method In which granules Including the composition of the present Invention are applied Into soll or on soil. Particulariy preferred soil application

215 methods Include spraying, stripe application, groove application, and planting hole application. Furthermore, application by Irrlgating soi! with a solution prepared by emulslfying or dissolving the composition of the présent Invention In water ls also a preferred soil application method.

Besides these methods, examples of preferred soi! application methods include application into a nutrient solution in nutrient solution culture Systems such as solid medium culture, for example, hydroponic culture, sand culture, NFT (nutrient film technique), rock wool culture and the like for the production of vegetables and flowering plants, or application Into a nursery box for paddy rice seedling (mlxlng with bed soll and the like). The compound of the présent invention may be applied directly to artificial culture soll including vermiculite and a solid medium Including an artificial mat for growing seedling.

The throughput ofthe composition ofthe présent invention Into water surface, a nursery box or soll ls not particulariy limited, but is 0.1 g to 10 kg of preferably active ingrédients per 10 ares of cultivated iand and preferably 1 g to 1 kg. Further, as the method for applying the composition or combined product of the présent invention to an applied organism, It ls possible to control pests by administering the pest control composition of the présent invention Into the applied organism either orally or by injection, wholly or partly administering the composition into the body surface of an applied animal, or mounting the pest control agent formulated Into a resin préparation or sheet préparation on the applied organism. In addition, it is also possible to control pests by covering places in which the invasion, parasitism and movement of pests are expected with the pest control composition of the présent invention.

The pest control composition of the présent Invention may be used as It is, but may be diluted with water, liquid carriers, commercially avaiiable shampoos, rinses, balts, breed cage bottoms and the like and applied In some cases. When the pest control composition of the présent invention ls diluted with a dilution liquid (water) such as an emulsifiable concentrate, a flowable and a wettable powder and used, the amount ls not particulariy limited, but, preferably, the composition is applied by diluting the composition In water and spraying the mixture such

216 that the concentration of active ingrédients is 10 to 10,000 ppm. Furthermore, when the pest control composition of the présent invention Is administered to a target organisai, the administration amount thereof is not particulariy limited, but when the composition is percutaneouslyapplied, the amount ofthe composition is preferablyin a range from 0.01 to 500 mg per 1 kg of the body weight of the target organisai. When the composition is orally administered, the amount of the composition is in a range from 0.01 to 100 mg per 1 kg of the body weight of the target organisai. When a resin préparation is mounted on the target organisai, the amount of the composition contained In the resin préparation Is preferably in a range from 0.01 to 50% by weight perweightofthe resin préparation.

[Examples]

Herelnafter, the présent invention wili be specifically described with reference to Examples, but the présent invention is not limited to the Examples.

Synthetic Exampie PI: N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2trifluoroacetamlde (Compound P212) (1 ) 25 g (270 mmol) of 2-aminopyridine was dissolved in 200 mi of anhydrous dichloromethane, 41 ml (30 g, 300 mmol) of triethylamlne was added thereto, and the mixture was cooled to 0°C. 38 ml (57 g, 270 mmol) of anhydrous trifluoroacetlc acid was added dropwise thereto over 15 minutes, and the resulting mixture was stined at room température for 2 hours. After the réaction was completed, the reaction solution was Injected Into about 100 mi of iced water, and the mixture was stirred for 10 minutes. The mixture was transferred to a separatory funnel to perform liquid séparation, and the organic layer was washed twice with 150 ml of water and twice with 150 m! of a 1% HCI aqueous solution, dried over anhydrous magnésium sulfate and concentrated under reduced pressure to obtain 36 g (yleld 71%) of 2,2,2-trifluoro-N-(pyridÎn-2(1H)-ylidene)acetamlde.

1H-NMR (CDCI3, δ, ppm): 7.20(1H, ddd), 7.83(1H, td), 8.20(1H, d), 8.35(1H, d), 10.07(1 H, brs)

13C-NMR (CDCI3, δ, ppm): 115.3,115.5(q), 121.6,139.1,147.9,149,5,155.3(q)

217

MS: m/z =191 (M+H) (2) 20 g (126 mmol) of 2-chloro-5-chloromethyl pyridine was dissolved in 200 ml of anhydrous acetonitrile, 24 g (126 mmol) of 2,2,2-trifluoro-N-(pyridin-2(1H)-ylidene)acetamide obtained by the above-described method and 21 g (151 mmol) of potassium carbonate were added thereto, and the resuiting mixture was heated and refluxed for 6 hours, and then stirred at room température for 10 hours. After the reaction was completed, the reaction solution was filtered and the liquid was concentrated under reduced pressure. Diethyt ether was added thereto for crystalllzation, and the crystals thus obtained were coliected and washed well with diethyl ether and water. The crystals thus obtained were dried under reduced pressure at 60’C for 1 hour to obtain the subject material. Amount obtained 26 g (yield 66%).

1H-NMR (CDCI3, δ, ppm): 5.57(2H, s), 6.92(1H, td), 7.31(1 H. d), 7.80(1H, td), 7.87(1H, dd), 7.99(1 H, dd), 8.48(2H, m)

13C-NMR (CDCI3, δ, ppm): 53.8, 115.5, 1l7.2(q), 122.1,124.7,130.0,139.2,140.0, 142.5, 149.7,151.8,158.9, 163.5(q)

MS: m/z = 316(M+H) (3) Powder X-ray crystal analysis

In the powder X-ray diffraction, measurement was performed under the following conditions.

Device name: RINT-2200 (Rigaku Corporation)

X-ray: Cu-Kot (40 kV, 20 mA)

Scanning range: 4 to 40°, sampling width: 0.02’ and scanning rate: 1°/min

The results are as follows.

Diffraction angle (2Θ) 8.7’, 14.2°, 17.5’, 18.3°, 19.8°, 22.4°, 30.9’ and 35.3’ (4) Differential Scanning Calorimetry (DSC) ln the differential scanning calorimetry, measurement was performed under the following conditions.

Device name: DSC-60

218

Sample cell: alumlnum

Température range: 50°C to 250°C (heating rate: 10°C/min)

As a resuit, the melting point was observed at 155°C to 158°C.

Another method of Synthetic Example P1

3.00 g (18.6 mmol) of 2-chloro-5-chloromethyt pyridine was dissolved in 20 ml of anhydrous DMF, 1.75 g (18.6 mmol) of 2-aminopyridine was added thereto, and the resulting mixture was stirred at 80°C for 8 hours and at room température for 5 hours. After the reaction was completed, DMF was distilled off under reduced pressure, acetonitrile was added thereto to precipitate a solid, and the solid was collected, washed well with acetonitrile and dried to obtain 2.07 g (yield 44%) of 1-[(6-chloropyridin-3-yl)methyl]pyridin-2(1H)-imine hydrochloride.

1H-NMR (DMSO-d6, δ, ppm): 5.65(2H, s), 6.96(1 H, t), 7.23(1 H, m), 7.57(1 H, d), 7.80(1 H, m), 7.91 (1 H, m), 8.28(1H, m), 8.49(1H, d), 9.13(2H, brs) mg (0.20 mmol) of the 1-[(6-chloropyridin-3-yl)methyi]pyridin-2(1H)-imine hydrochloride obtained by the above-described method was dissolved in 5 ml of anhydrous dichloromethane, 122 mg (1.00 mmol)of DMAP and 50 mg (0.24 mmol) of anhydrous trifluoroacetic acid were added thereto in sequence under ice cold conditions, and the resulting mixture was stirred at room température for 1 hour. After the reaction was completed, the reaction solution was diluted with dichloromethane, washed with 1% hydrochloric acid, and then dried over anhydrous magnésium sulfate. Dichloromethane was distilled off under reduced pressure to obtain the subject material. Amount obtained 42 mg (yield 67%). NMR was the same as that of the above-described method.

Synthetic Example P2:2,2-dibromo-N-[1-((6-chloropyTidin-3-yl)methyl)pyridin-2(1H)ylidenej-acetamide (Compound P241)

200 mg (0.78 mmol)ofthe 1-[(6-chloropyridin-3-yl)methyi]pyridin-2(1H)-imine hydrochloride obtained by the method described in another method of Synthetic Example P1, 238 mg (1.95 mmol) of DMAP and 224 mg (1.17 mmol) of EDC-HCI were dissolved in 10 ml of

219 anhydrous dichloromethane, 101 μΙ (202 mg, 1.17 mmol) of dibromoacetic acid was added thereto, and the resulting mixture was stirred at room température ovemight. After the réaction was completed, the réaction solution was diluted with dichloromethane, washed once with water and twice with a 1% HCl aqueous solution, and then dried over anhydrous magnésium sulfate and concentrated under reduced pressure to obtain the subject material. Amount obtained 50 mg (yieid 15%)

1H-NMR (CDCI3, δ, ppm): 5.56(2H, s), 5.99(1 H, s), 6.78(1 H, td), 7.33(1 H, d), 7.69(1 H, td). 7.76(1 H, dd), 7.93(1 H, dd). 8.39(1 H, d), 8.50(1 H, d)

13C-NMR (CDCI3, δ, ppm): 44.6, 53.1,113.7,121.9,124.8,130.1,138.2,139.7,141.2, 149.5,152.0, 159.4,172.2

MS: m/z = 418(M+H)

Synthetic Example P3: N-[1-((6-chioro-5-fluoropyridin-3-yl)methyl)pyridÎn-2(1H)-ylidene]2,2,2’trifluoroacetamlde (Compound P227)

4.00 g (27.6 mmol) of 2-chloro-3-fluoro-5-methyl pyridine was dissolved in 80 ml of carbon tetrachloride, 7.37 g (41.4 mmol) of N-bromosuccInlmide and 20 mg of benzoyl peroxlde were added thereto, and the resulting mixture was heated and refluxed ovemight. After the reaction was completed, the reaction solution was retumed to room température, concentrated under reduced pressure and purified by silica gel column chromatography (hexane: ethyl acetate = 19:1) to obtain 3.06 g (yieid 51%) of 5-(bromomethyl)-2’Chloro-3fluoropyridine.

1H-NMR (CDCI3, δ, ppm): 4.45(2H, s), 7.54(1 H, dd). 8.23(1 H, s) mg (0.22 mmol) of the 5-(bromomethyl)-2-chloro-3-fluoropyridine obtained by the aforementioned method was dissolved in 5 ml of anhydrous acetonitrile, 42 mg (0.22 mmol) of 2,2,2-trifluoro-N-(pyridin-2(1H)-ylidene)acetoamide obtained by the method described in (1 ) of Référencé Example 1 and 36 mg (0.26 mmol) of potassium carbonate were added thereto in sequence, and the resulting mixture was heated and refluxed for 7 hours. After the reaction was completed, the réaction solution was retumed to room température to filter insoluble

220 materiais, and the filtrate was concentrated under reduced pressure. Diethyl ether was added thereto to precipitate a solid, and thus the solid was collected, washed with diethyl ether, and then dried under reduced pressure in a desiccator to obtain the subject material. Amount obtained 29 mg (yield 40%).

1H-NMR (CDCI3, δ, ppm): 5.54(2H, s), 6.89(1 H, td), 7.76(1 H, dd), 7.80(1 H, td), 7.85(1 H, d), 8.29(1 H, d), 8.57(1 H. d)

MS: m/z - 334(M+H)

Synthetic Example P4: N-[1-((6-fluoropyridÎn-3-yl)methyl)pyridin-2(1H)-ylidenel-2,2,2trifluoroacetamlde (Compound P229)

500 mg (4.50 mmol) of 2-fluoro-5-methyl pyridine was dissolved In 50 ml of carbon tetrachloride, 1.20 g (6.76 mmol) of N-bromosuccinimide and 20 mg of benzoyl peroxlde were added thereto, and the resulting mixture was heated and refluxed for 2.5 hours. After the reaction was completed, the reaction solution was retumed to room température, and the solvent was distilled off under reduced pressure and purified by silica gei column chromatography (hexane: ethyi acetate = 19:1) to obtain 300 mg (yield 35%) of 5bromomethyl-2-fluoropyridine.

mg (0.30 mmoi) of the 5-bromomethyl-2-fluoropyridine obtained by the aforementioned method was dissolved in 10 ml of anhydrous acetonitrile, 57 mg (0.30 mmol) of 2,2,2-trifluoro-N-(pyridin-2(1H)-ylidene)acetoamide synthesized by the method described In (1) of Synthetic Example P1 and 69 mg (0.50 mmol) of potassium carbonate were added thereto in sequence, and the resulting mixture was heated and refluxed for 6 hours. After the reaction was completed, the reaction solution was retumed to room température to filter Insoluble materiais, and the filtrate was concentrated under reduced pressure. The filtrate was purified by silica gel column chromatography (hexane: ethyi acetate =1:1—>3:1)to obtain the subject material. Amount obtained 21 mg (yield 23%).

1H-NMR (CDCI3, δ, ppm): 5.56(2H, s), 6.89(1 H, td), 6.94(1 H, d), 7.79(1 H, td), 7.87(1 H. d), 8.03(1 H, m), 8.31(1 H, s), 8.54(1 H, d)

221

MS: m/z - 300(M+H)

Synthetic Example P5: N-[1-((6-bromopyridin-3-yl)methy1)pyridin-2(1H)-y1idene]-2,2,2trifluoroacetamide (Compound P231)

500 mg (2.92 mmol) of 2-bromo-5-methy1pyridine was dissolved In 15 ml of carbon tetrachloride, 623 mg (3.50 mmol) of N-bromosuccinimide and 10 mg of benzoyl peroxide were added thereto, and the resulting mixture was heated and refluxed for 19 hours. After the reaction was completed, the reaction solution was retumed to room température, concentrated under reduced pressure and purified by silica gel column chromatography (hexane: ethyl acetate = 19:1) to obtain 143 mg (yield 20%) of 2-bromo-5-bromomethy1pyridine.

1H-NMR (CDCI3, δ, ppm): 4.42(2H, s), 7.47(1 H, d), 7.59(1 H, dd), 8.38(1 H, d) mg (0.28 mmol) of the 2-bromo-5-bromomethylpyridine obtained by the aforementioned method was dissolved In 10 ml of anhydrous acetonitrile, 54 mg (0.28 mmol) of 2,2,2-trifluoro-N-(pyridin-2(1H)-y1idene)acetoamlde synthesized by the method described In (1) of Synthetic Example P1 and 46 mg (0.34 mmol) of potassium carbonate were added thereto in sequence, and the resulting mixture was heated and refluxed for 6 hours. After the reaction was completed, the reaction solution was retumed to room température to filter Insoluble materials, and the filtrate was concentrated under reduced pressure. Diethyl ether was added thereto to precipitate a solid, and thus the solid was collected, washed with diethyl ether, and then dried under reduced pressure In a deslccator to obtain the subject material. Amount obtained 81 mg (yield 82%).

1H-NMR (CDCI3, δ, ppm): 5.52(2H, s), 6.88(1 H, t), 7.48(1 H, d), 7.78(2H, m), 7.84(1 H, d), 8.44(1 H, d), 8.53(1 H, d)

MS: m/z = 360(M+H)

Synthetic Example P6: 2-chtoro-N-[1-((6-chloropyridin-3-y1)methy1)pyridin-2(1H)ylidenej-acetamide (Compound P236) mg (0.27 mmol) of the 1-[(6-chloropyridin-3-yl)methyl]pyridin-2(1H)-lmine hydrochloride obtained by the method described in another method of Synthetic Example P1

222 was dissolved in 4ml of anhydrous dichloromethane, 82 mg (0.67 mmol) of DMAP, 25 mg (0.27 mmol) of chloroacetic acid and 62 mg (0.32 mmol) of EDC-HCI were added thereto In sequence, and the resulting mixture was stirred at room température ovemlght. After the reaction was completed, dichloromethane was added thereto to dilute the mixture, and the mixture was washed with water and a 1% HCl aqueous solution, dried over anhydrous magnésium sulfate and concentrated under reduced pressure to obtaln the subject material. Amount obtained 4 mg (yield 5%).

1H-NMR (CDCI3, δ, ppm): 4.17(2H, s), 5.46(2H, s), 6.64(1 H, td), 7.31(1 H. d), 7.60(1 H. td), 7.64(1 H, dd), 7.80(1 H, dd), 8.32(1 H, d). 8.45(1 H. d)

MS: m/z = 296(M+H)

Synthetic Example P7: N-[1-((6-chloropyridin-3-yl)methyl)pyrldin-2(1H)-yiidene]-2,2difluoroacetamlde (Compound P238)

400 mg (4.26 mmol) of 2-aminopyridine was dissolved in 10 ml of anhydrous dichloromethane, 322 μΐ (490 mg, 5.11 mmol) of difluoroacetic acid, 982 mg (5.10 mmol) of EDC-HCI and 622 mg (5.11 mmol) of DMAP were added thereto, and the resulting mixture was stirred at room température for 61 hours. After the reaction was completed, the reaction solution was diluted with dichloromethane, washed once with water and twlce with a 1% HCl aqueous solution, and then dried over anhydrous magnésium sulfate and concentrated under reduced pressure to obtain 102 mg (yield 14%) of 2,2-difluoro-N-(pyTidin-2(1H)y!idene)acetamide.

1H-NMR (CDCI3, δ, ppm): 6.03(1 H, t), 7.15(1 H, m), 7.78(1 H. td), 8.20(1 H. d), 8.34(1 H, dd). 8.72(1H, brs)

100 mg (0.58 mmol) of the 2,2-difluoro-N-(pyridin-2(1H)-ylidene)acetamide obtained by the aforementioned method was dissolved In 10 ml of anhydrous acetonitrile, 94 mg (0.58 mmol) of 2-chloro-5-chloromethy! pyridine was dissolved ln 5 ml of anhydrous acetonitrile and added thereto, and subsequently, 84 mg (0.63 mmol) of potassium carbonate was added thereto and the resulting mixture was heated and refluxed for 140 minutes. After the réaction

223 was completed, the reaction solution was retumed to room température to filter off Insoluble materials, and the filtrate was concentrated under reduced pressure. Ether was added thereto to predpitate a solid, and thus the solid was collected and dried well to obtain the subject material. Amount obtained 63 mg (yield 37%).

1H-NMR (CDCI3, 5, ppm): 5.52(2H, s), 5.90(1 H, t), 6.79(1 H, td), 7.33(1 H, d), 7.71(1 H, m), 7.77(1 H, dd), 7.85(1 H, dd), 8.45(1 H, d), 8.50(1 H, d)

13C-NMR (DMSO-d6, 6, ppm): 53.0,111.0(t), 115.2,120.7,124.7,131.7, 140.6,141. 6, 143.2,150.4,150.9,158.3,169.4(t)

MS: m/z « 298(M+H)

Synthetic Example P8: 2-chloro-N-[1-((6-chloropyridin-3-y1)methy1)pyridin-2(1H)ylidene]-2,2-difluoroacetamide (Compound P239)

200 mg (2.13 mmol) of 2-aminopyridine was dissoived In 5 ml of dichloromethane, 491 mg (2.55 mmol) of EDC-HCI, 311 mg (2.55 mmol) of DMAP and 187 μΙ (2.23 mmol, 290 mg) of chlorodifluoroacetic acid were added thereto In sequence, and the resulting mixture was stirred overnight. After the reaction was completed, the reaction solution was diluted with dichloromethane, washed with water and 1% hydrochloric acid, and then dried over anhydrous magnésium sulfate to obtain 105 mg (yield 24%) of 2-chloro-2,2-difluoro-N-(pyridÎn-2(1H)ylidene)acetamide.

1H-NMR (CDCI3, 5, ppm): 7.19(1 H, dd), 7.82(1 H, m), 8.18(1 H, d), 8.36(1 H, d), 9.35(1 H, brs) mg (0.33 mmol) of 2-chloro-5-chloromethyl pyridine dissoived in 6 ml of anhydrous acetonitrile was added to 68 mg (0.33 mmol) of the 2-chloro-2,2-difluoro-N-(pyridin-2(1H)ylidene)acetamide synthesized by the aforementioned method, and subsequently, 50 mg (0.36 mmol) of potassium carbonate was added thereto and the resulting mixture was heated and refluxed for 1 hours. After the reaction was completed, the reaction solution was retumed to room température and then concentrated under reduced pressure. Diethyl ether was added thereto to precipitate a solid, and thus the solid was collected and dried to obtain the subject

224 material. Amount obtained 49 mg (yield 45%).

1H-NMR (CDCI3, 5, ppm): 5.56(2H, s), 6.92(1H, t), 7.33(1H, d), 7.82(1H, m), 7.91(1H, dd), 8.02(1 H, d), 8.45(1 H, d). 8.48(1 H, d)

13C-NMR (CDCI3, 6, ppm): 53.8,115.2, 120.1(t), 122.1,124.8,139.0,140.0,142.3, 150.0,151.9,159.1,159.1,165.8(t)

MS: m/z = 332(M+H)

Synthetic Example P9: 2,2,2-trichloro-N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)ylidenej-acetamide (Compound P235) mg (0.27 mmol) of the 1-[(6-chloropyridin-3-y1)methyl]pyridin-2(1H)-lmlne hydrochloride obtained by the method described ln another method of Synthetic Example P1 was dissolved ln 4 ml of anhydrous dlchloromethane, 94 μΙ (0.68 mmol, 68 mg) of triethylamine and 33 pg (0.27 mmol, 49 mg) of trichloroacetyl chloride were added thereto in sequence, and the resulting mixture was stirred at room température for 1 hour. After the reaction was completed, water was added thereto to stop the reaction and liquid séparation was performed with dlchloromethane and water. The organic layer was washed once with water and twice with 1% hydrochloric acid, dried over anhydrous magnésium sulfate and concentrated under reduced pressure. Diethyl ether was added thereto to preclpitate a solid, and thus the solid was collected and dried to obtain the subject material. Amount obtained 61 mg (yield 62%).

1H-NMR (CDCI3, 5, ppm): 5.59(2H, s), 6.86(1 H, t), 7.32(1 H, d), 7.78(1 H, td), 7.91 (2H, m), 8.43(1 H, d). 8.50(1 H, d)

MS: m/z = 364(M+H)

Synthetic Example P10: N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]2,2,3,3,3-pentafluoropropanamide (Compound P242)

300 mg (3.19 mmol) of 2-aminopyridine was dissolved in 15 ml of anhydrous dlchloromethane, 919 mg (4.78 mmol) of EDC-HCI, 583 mg (4.78 mmol) of DMAP and 397 μΙ (628 mg, 3.83 mmol) of pentafluoroproplonic add were added thereto in sequence, and the

225 resulting mixture was stirred at room température ovemight. After the reaction was completed, the reaction solution was diluted with dichloromethane, washed once with water and twlce with 1% hydrochloric acid, and then dried over anhydrous magnésium sulfate and concentrated under reduced pressure to obtain 85 mg (yield 11%) of 2,2,3,3,3-pentafluoro-N(pyridin-2(1H)-ylidene)piOpanamide.

mg (0.32 mmol) of 2-chloro-5-chloromethy! pyridine dissolved ln 8 ml of anhydrous acetonîtrile and 49 mg (0.35 mmol) of potassium carbonate were added to 77 mg (0.32 mmol) of the 2,2,3,3,3-pentafluoro-N-(pyridin’2(1H)-ylidene)propanamide obtained by the aforementioned method, and the resulting mixture was heated and refluxed for 11 hours. After the reaction was completed, the reaction solution was retumed to room température to filter insoluble materials, and the filtrate was concentrated under reduced pressure. The filtrate was purified by silica gel column chromatography (hexane: ethyl acetate = 1:3) to obtain the subject material. Amount obtained 12 mg (yield 10%).

1H-NMR (CDCI3, δ, ppm): 5.56(2H, s), 6.90(1H, td), 7.32(1 H, d), 7.79(2H, m), 7.84(1H, d), 8.43(1 H, d), 8.56( 1 H, d)

MS: m/z = 366(M+H)

Synthetic Example P11: N-[1-((2-chloropyrimidin-5-yl)methyl)pyridin-2(1H)-y!idene]2,2,2-trifluoroacetamide (Compound P243)

1.04 g (8.13 mmol) of 2-chloro-5-methyl pyrimidine was dissolved in 30 ml of carbon tetrachloride, 1.73 g (9.75 mmol) of N-bromosuccinimide and 20 mg of benzoy! peroxide were added thereto, and the resulting mixture was heated and refluxed for 6 hours. After the reaction was completed, the reaction solution was retumed to room température, concentrated under reduced pressure and purified by silica gel column chromatography (hexane: ethyl acetate = 3:1) to obtain 641 mg (yield 38%) of 5-bromomethyi-2-chloropyridine.

1H-NMR (CDCI3, δ, ppm): 4.42(2H, s), 8.66(2H, s)

104 mg (0.50 mmol) of the 5-bromomethyl-2-chloropyridine obtained by the aforementioned method was dissolved in 6 ml of anhydrous acetonitrile, 96 mg (0.50 mmol) of

226

2,2,2-trifluoro-N-(pyridin-2(1H)-ylidene)acetoamide obtained by the method described in (1) of Synthetic Example P1 and 76 mg (0.55 mmol) of potassium carbonate were added thereto, and the resulting mixture was heated and refluxed for 1 hour. After the réaction was completed, the reaction solution was retumed to room température to filter off insoluble materials, and the filtrate was concentrated under reduced pressure. Diethyl ether was added thereto to precipitate a solid, and thus the solid was coliected, washed with diethyl ether, and then dried under reduced pressure in a desiccator to obtain the subject material. Amount obtained 92 mg (yield 58%).

1H-NMR (CDCI3, δ, ppm): 5.54(2H, s), 6.98(1 H, m), 7.87(1 H, m), 8.18(1 H, m), 8.48(1 H, 10 m), 8.83(2H, m)

13C-NMR (CDCI3, δ, ppm): 60.0,115.6,117.1(q), 122.1, 127.5,139.2,142.9,158.8, 160.3(20), 161.4,163.8(q)

MS: m/z = 317(M+H)

The compounds of P213 to P226, P228, P230, P232 to P234, P240 and P244 shown in the following Table were syntheslzed by the methods in accordance with Synthetic Examples P1 toP11.

[Table 40-1]

Compo und No.	Ar	R1a	Y	¹H-NMR (CDCI3, δ, ppm)	IR (KBr, v, cm'¹) or MS
P212	6-chloro-3pyridyl	CF3	H	5.57 (2H, s), 6.92 (1 H. td), 7.31 (1H. d), 7.80 (1H, td), 7.87 (1H, dd), 7.99 (1H. dd), 8.48 (2H, m)	m/z = 316 (M+H)
P213	2-chloro-5thiazolyl	CF3	H	5.61 (2H, s), 6.93 (1H, dd), 7.68(1 H, s), 7.83 (1H, td), 7.97 (1H, d), 8.53 (1 H, d)	m/z = 322 (M+H)
P214	6-chloro-3pyridyl	OCH 3	H	3.74 (3H, s), 5.40 (2H, s), 6.45 (1H. td), 7.29 (1H, d), 7.46 (2H, m), 7.73 (1H, dd), 8.12 (1H. dd), 8.40 (1H, d)	m/z = 278 (M+H)

227

P215	6-chloro-3pyrldyl	CF3	5Cl	5.53 (2H, S), 7.34 (1H, d), 7.71 (1 H. dd), 7.87 (1H, dd), 7.94 (1H, S), 8.49 (1 H. d), 8.55 (1 H. s)	m/z = 350 (M+H)
P216	6-chioro-3pyridyl	CF3	5-F	5.54 (2H, s), 7.34 (1H, d), 7.70 (1H, m), 7.80 (1 H, m), 7.88 (1H, dd), 8.48 (1H, d), 8.64 (1H, m)	m/z = 334 (M+H)
P217	6-chloro-3pyridyl	CF3	4Cl	5.49 (2H, s), 6.85 (1H. dd), 7.35 (1H, d), 7.76 (1H, dd), 7.85 (1H, dd), 8.44 (1H, d), 8.62 (1H. s)	m/z = 350 (M+H)
P218	2-chloro-5thlazolyl	CF3	5Cl	5.56 (2H, S), 7.68 (1H. s), 7.74 (1H, dd), 7.84 (1H, d), 8.58 (1 H. d)	m/z = 356 (M+H)

[Table 40-2]

P219	2-chloro-5thlazolyl	CF3	5F	5.60 (2H, s), 7.69 (1H, s), 7.72 (1H, td), 7.86 (1H, m), 8.67 (1H, m)	m/z = 340 (M+H)
P220	2-chloro-5thiazolyl	CF3	4Cl	5.58 (2H, s), 6.90 (1H, d), 7.67 (1H, s), 7.90 (1H, d), 8.61 (1H, s)	m/z = 356 (M+H)
P221	6-chloro-3pyridyl	CF3	3M e	2.31 (3H, s), 5.50 (2H, s), 6.98 (1H, m). 7.34 (1H, d), 7.73 (1H, dd), 7.77 (2H, m), 8.42 (1H, d)	m/z = 330 (M+H)
P222	6-chloro-3pyridyl	CF3	4M e	2.40 (3H, S), 5.49 (2H, s), 6.70 (1H, dd), 7.32 (1H, d), 7.70 (1H, d), 7.86 (1H, dd), 8.37 (1H, s), 8.43 (1H, d)	m/z = 330 (M+H)
P223	6-chloro-3pyridyl	CF3	5M e	2.29 (3H, S), 5.52 (2H, s), 7.32 (1H, d). 7.62 (1 H, s). 7.65 (1H, dd), 7.88 (1H, dd), 8.46 (1H. d), 8.50 (1 H. d)	m/z = 330 (M+H)
P224	phenyl	CF3	H	5.58 (2H, s), 6.81 (1 H. m), 7.37 (4H, m), 7.77 (2H, m), 8.50 (1H, d)	m/z - 281 (M+H)
P225	4-chlorophenyl	CF3	H	5.52 (2H, s), 6.85 (1H, m), 7.30 (2H, d), 7.36 (2H, d), 7.75 (1H, td), 7.84 (1H, d), 8.47 (1H, d)	m/z =315 (M+H)
P226	3-pyrldyl	CF3	H	5.57 (2H, s), 6.86 (1H, m), 7.26-7.35 (2H. m), 7.78 (1H, td), 7.86 (1H, m), 8.63 (2H. m), 8.67 (1H, d)	m/z = 282 (M+H)
P227	6-chloro-5fluoro-3pyrldyl	CF3	H	5.54 (2H, s), 6.89 (1 H, td), 7.76 (1H, dd), 7.80 ( 1 H, td), 7.85 (1H, d), 8.29 (1H, d), 8.57 (1H, d)	m/z = 334 (M+H)

228 [Table 40-3]

P228	6trifluoromethyl3- pyridyl	CF3	H	5.62 (2H, S), 6.90 (1H, t), 7.69 (1H, d), 7.81 (1H, t), 7.88 (1H. d). 8.06 (1H, d), 8.56 (1H, d), 8.78 (1H, s)	m/z = 350 (M+H)
P229	6-fluoro-3pyrldyl	CF3	H	5.56 (2H, s), 6.89 (1H, td), 6.94 (1H, d), 7.79 (1H. td), 7.87 (1H, d), 8.03 (1H, m), 8.31 (1H, s), 8.54 (1H, d)	m/z = 300 (M+H)
P230	5,6-dichloro-3pyridyl	CF3	H	5.49 (2H, s), 6.89 (1 H, t), 7.79-7.90 (2H, m), 8.04 (1 H. d), 8.37 (1H. d). 8.56 (1H, m)	m/z = 350 (M+H)

[Table 41-1]

Compo und No.	Ar	R1a	Y	’H-NMR (CDCI3, δ, ppm)	IR (KBr, v, cm'¹) or MS
P231	6-bromo-3pyridyl	CF3	H	5.52 (2H, s), 6.88 (1H. t), 7.48 (1H. d), 7.78 (2H, m), 7.84 (1H, d), 8.44 (1H, d), 8.53 (1H, d)	m/z = 360 (M+H)
P232	6-chioro-3pyridyl	CF3	4-F	5.52 (2H, s), 6.71 (1H, m), 7.35 (1H, d), 7.86 (1H, dd), 7.94 (1H. m), 8.33 (1H, dd), 8.44 (1H, d)	m/z = 334 (M+H)
P233	6-chloro-3pyridyl	CF3	3-F	5.53 (2H, s). 6.74 (1H, m). 7.33 (1H, d), 7.87 (1H, dd). 8.07 (1H. m), 8.29 (1H, dd), 8.45 (1H. d)	m/z = 334 (M+H)
P234	6-chloro-3pyridyl	CHCI 2	H	5.54 (2H. S), 6.02 (1H, s), 6.77 (1H, t), 7.32 (1H, m), 7.69 (1H, m), 7.77 (1H, d), 7.89 (1H, m), 8.42 (1H, m), 8.49 (1H, s)	m/z = 330 (M+H)
P235	6-chloro-3pyridyl	CCI3	H	5.59 (2H, S), 6.86 (1H, t), 7.32 (1H, d), 7.78 (1H, td), 7.91 (2H, m), 8.43 (1H, d), 8.50 (1H, d)	m/z = 364 (M+H)
P236	6-chloro-3pyridyl	CH2 Cl	H	4.17 (2H, s), 5.46 (2H, s), 6.64 (1H, td), 7.31 (1H, d), 7.60 (1H, td), 7.64 (1H, dd), 7.80 (1H, dd), 8.32 (1H, d), 8.45 (1H, d)	m/z = 296 (M+H)

229 fiable 41-2]

P238	6-chloro-3pyridyl	CHF2	H	5.52 (2H, s), 5.90 (1H, t), 6.79 (1H, td), 7.33 (1H, d), 7.71 (1H, m), 7.77 (1H, dd), 7.85 (1H, dd), 8.45 (1H, d), 8.50 (1H, d)	m/z = 298 (M+H)
P239	6-ch!oro-3pyrldyl	CF2C I	H	5.56 (2H, s), 6.92 (1H, t), 7.33 (1H, d), 7.82 (1H, m), 7.91 (1H, dd), 8.02 (1H, d), 8,45 (1H, d), 8.48 (1H, d)	m/z = 332 (M+H)
P240	6-chloro-3pyrldy!	CHCI Br	H	5.53 (1H, d), 5.58 (1H, d), 6.06 (1H, s), 6.76 (1H, td), 7.32 (1H, d), 7.69 (1H, m), 7.70 (1H, m), 7.90 (1H, dd), 8.40 (1H, d), 8.50 (1H, d)	m/z - 374 (M+H)
P241	6-chloro-3pyrldy!	CHBr 2	H	5.56 (2H, s), 5.99 (1H. s), 6.78 (1H. td), 7.33 (1H, d), 7.69 (1H, td), 7.76 (1H, dd), 7.93 (1H, dd), 8.39 (1H, d), 8.50 (1H. d)	m/z = 418 (M+H)
P242	6-chloro-3pyrldyl	CF2C F 3	H	5.56 (2H, s), 6.90 (1H, td), 7.32 (1H, d), 7.79 (2H, m), 7.84 (1H, d), 8.43 (1 H, d), 8.56 (1H, d)	m/z = 366 (M+H)
P243	2-chloro-5pyrimld Inyl	CF3	H	5.54 (2H, s), 6.98 (1H, m), 7.87 (1H, m), 8.18 (1H, m), 8.48 (1H, m), 8.83 (2H, m)	m/z = 317 (M+H)
P244	6-chloro-3pyrldyl	CH2 Br	H	4.17 (2H, s), 5.46 (2H, s), 6.63 (1H, td), 7.31 (1H, d), 7.60 (1H, td), 7.65 (1H, dd), 7.80 (1H, dd), 8.32 (1H, d), 8.47 (1H. d)

Synthetic Example 1:2,2-difluoro-N-[1-((6-fluoropyridin-3-yl)methy!)pyridin-2(1H)5 ylidene]acetamlde (Compound 3-3) [Chemical Formula 46]

F

(1) 400 mg (4.26 mmol) of 2-aminopyridine was dissolved in 10 m! of anhydrous dichloromethane, 322 μ! (490 mg, 5.11 mmol) of difluoroacetic acid, 982 mg (5.10 mmol) of

230

EDC-HCI and 622 mg (5.11 mmol) of DMAP were added thereto, and the resulting mixture was stirred at room température for 61 hours. After the reaction was completed, the reaction solution was diluted with dichloromethane, washed once with water and twice with a 1% HCl aqueous solution, and then dried over anhydrous magnésium sulfate and concentrated under reduced pressure to obtain 102 mg (yield 14%) of 2,2-difluoro-N-(pyridin-2(1H)ylidene)acetamide.

1H-NMR (CDCI3, δ. ppm): 6,03(1 H. t), 7.15(1 H, m), 7.78(1 H. td>, 8.20(1 H. d). 8.34(1 H, dd), 8.72(1 H, brs) (2) 128 mg (0.75 mmol) of 5-bromomethyl-2-fluoropyridine was dîssolved in 3 ml of anhydrous DMF, 116 mg (0.68 mmol)of 2,2-difluoro-N-[pyridin-2(1H)-ylidene]acetamide was dîssolved in 3 ml of anhydrous DMF and added thereto, and subsequently, 103 mg (0.75 mmol) of potassium carbonate was added thereto and the resulting mixture was stirred at 65°C for 2 hours. After the réaction was completed, the reaction solution was retumed to room température, and ethyl acetate and water were added thereto to perform liquid séparation. The organic layer was washed with 1 % hydrochlorlc acid, then dried over anhydrous magnésium sulfate and concentrated under reduced pressure. A small amount of hexane and diethyl ether were added thereto to predpitate crystals, and thus the crystals were collected and dried to obtain the subject material. Amount obtained 50 mg (yield 26%).

Synthetic Example 2: N-[1-((6-chloropyridin-3-yl)methyl)pyrimidin-2(1H)-ylidene]-2,2,2trifluoroacetamide (Compound 190-2) [Chemical Formula 47] (1 ) 300 mg (1.86 mmol) of 2-chloro-5-chloromethyl pyridine was dîssolved In 6 ml of anhydrous DMF, 118 mg (1.24 mmol) of 2-aminopyrimldine was added thereto, and the resulting mixture was stirred at 80°C for 8 hours. After the reaction was completed, the

231 réaction solution was retumed to room température to distill off DMF under reduced pressure. Diethyl ether was added thereto, and thus crystallization was occurred on the wall surface of an eggplant flask. Diethyl ether was removed by décantation and dried well to obtain 1-((6chloropyrldin-3-yl)methyl)pyrimldin-2(1H)-lmine hydrochloride. Amount obtained 107 mg (yieid 34%) (2) 71 mg (0.27 mmol) of the 1-((6-chioropyridin-3-yl)methyl)pyrimldin-2(1H)-imine hydrochloride obtained by the aforementioned method was suspended In 5 ml of anhydrous dichloromethane, 114 μΐ (0.83 mmol, 83 mg) of triethylamine and 53 μΙ (0.38 mmol) of trifluoroacetic anhydride were added thereto In sequence, and the resulting mixture was stirred at room température for 2 hours. After the reaction was completed, dichloromethane and water were added to the reaction solution to perform liquid séparation, and the organic layer was dried over anhydrous magnésium sulfate and then concentrated under reduced pressure. A small amount of diethyl ether was added thereto to precipltate crystals, and thus the crystals were coliected, washed with a small amount of diethyl ether, and then dried to obtain the subject material. Amount obtained 24 mg (yieid 28%).

Synthetic Example 3:2,2,2-trifluoroethyl-[1-((6-chloropyridin-3-yl)methyl)pyridin-(2H)ylidenejcarbamate (Compound 1-17) [Chemical Formula 48] ci (1) 3.00 g (18.6 mmol) of 2-chloro-5-chloromethyl pyridine was dissoived In 20 ml of anhydrous DMF, 1.75 g (18.6 mmol) of 2-aminopyridine was added thereto, and the resulting mixture was stirred at 80°C for 8 hours and at room température for 5 hours. After the réaction was completed, DMF was distilled off under reduced pressure, acetonitrile was added thereto to preclpitate a solid, and the solid was coliected, washed well with acetonitrile and then dried to obtain 2.07 g (yieid 44%) of 1-[(6-chloropyridin-3-yl)methyl]pyridin-2(1H)-lmine

232 hydrochloride,

H-NMR (DMSO-d6, δ, ppm): 5.65(2H, s), 6.96(1 H, t), 7.23(1 H, m), 7.57(1 H. d), 7.80(1 H, m), 7.91(1 H, m), 8.28(1 H, m), 8.49(1 H, d) (2) 10 ml of anhydrous acetonitrile was added to 150 mg (0.66 mmol) ofthe 1-[(6chioropyridin-3-yl)methyl]pyridin-2(1H)-imine hydrochloride obtained by the aforementioned method, 177 mg (0.66 mmol) of 4-nitrophenyl (2,2,2-trifiuoroethyl)carbamate and 200 mg (1.46 mmol) of potassium carbonate were added, and the resulting mixture was stirred at 50°C for 2 hours. After the reaction was compieted, the reaction solution was retumed to room température to filler off insoluble materials, and the filtrate was concentrated under reduced pressure. Dichloromethane and water were added thereto to perform liquid séparation, and the organic layer was washed with 1% hydrochloric acid, then dried over anhydrous magnésium sulfate and concentrated under reduced pressure. A small amount of dîethyl ether was added thereto to precipîtate crystals, and thus the crystals were collected and dried well to obtain the subject material. Amount obtained 48 mg (yield 21%).

Synthetic Example 4: N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylÎdene]-2,2,2trifluoroethanethioamlde (Compound 1-20) [Chemical Formula 49]

s (1) 25 g (270 mmol) of 2-amlnopyridine was dissolved in 200 ml of anhydrous dichloromethane, 41 ml (30 g, 300 mmol) of triethylamine was added thereto, and the mixture was cooled to 0°C. 38 ml (57 g, 270 mmol) of anhydrous trifluoroacetic acid was added dropwise thereto over 15 minutes, and the resulting mixture was stirred at room température for 2 hours. After the reaction was compieted, the réaction solution was injected into about 100 ml of Iced water, and the mixture was stirred for 10 minutes. The mixture was transferred to a separatory funnel to perform liquid séparation, and the organic layer was washed twice

233 with 150 ml of water and twice with 150 ml of a 1% HCl aqueous solution, dried over anhydrous magnésium sulfate and concentrated under reduced pressure to obtain 36 g (yield 71%) of 2,2,2-trifluoro-N-(pyridin-2(1H)-ylidene)acetamide.

1H-NMR (CDCI3, δ, ppm): 7.20(1H, m), 7.83(1 H, m). 8.20(1H, d). 8.35(1H, d), 10.07(1H, brs)

13C-NMR (CDCI3, δ, ppm): 115.3,115.5(q), 121.6, 139.1,147.9, 149.5, 155.3(q) (2) 20 g (126 mmol) of 2-chloro-5-chloromethyl pyridine was dissolved in 200 ml of anhydrous acetonitrile, 24 g (126 mmol)of 2,2,2-trifluoro-N-(pyridin-2(1H)-ylidene)acetamide obtained by the above-described method and 21 g (151 mmol) of potassium carbonate were added thereto, and the resuiting mixture was heated and refluxed for 6 hours, and then stirred at room température for 10 hours. After the reaction was completed, the reaction solution was filtered and the filtrate was concentrated under reduced pressure. Diethyl ether was added thereto for crystallizatlon, and the crystals thus obtained were coliected and washed well with diethyl ether and water. The crystals thus obtained were dried under reduced pressure at 60°C for 1 hour to obtain N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-

2,2,2-trifluoroacetamide (P212). Amount obtained 26 g (yield 66%).

1H-NMR (CDCI3, δ, ppm): 5.57(2H, s), 6.92(1 H, td), 7.31(1 H, d), 7.80(1 H, td), 7.87(1 H, dd), 7.99(1 H, dd), 8,48(2H, m)

13C-NMR (CDCI3, δ, ppm): 53.8,115.5, 117.2(q), 122.1,124.7,130.0,139.2,140.0, 142.5, 149.7,151.8,158.9, 163.5(q)

MS: m/z = 316(M+H) (3) 180 ml of toluene was added to 16.3 g (36.7 mmol) of phosphorus pentasulflde, 6.72 g (63.4 mmol) of sodium carbonate was added thereto and the resuiting mixture was stirred at room température for 5 minutes. 20.0 g (63.4 mmol) of the N-[1 -((6-chloropyridin-3yl)methyl)pyridin-2(1H)-y1idene]-2,2,2-trifluoroacetamide obtained by the above-described method was added thereto, and the resuiting mixture was stirred at 50°C for 19 hours. 150 ml of ethyl acetate was added to the reaction solution, the resuiting mixture was stirred at 50°C

234 for 10 minutes, then insoluble materials were filtered off, and 250 ml of ethyl acetate was used to wash the mixture. The mixture was transferred to a separatory funnel, washed therein with 300 ml of a saturated sodium bicarbonate water and 200 ml of a saturated saline solution, and then concentrated under reduced pressure. 200 ml of water was added thereto to predpitate crystals. The mixture was stirred at room température for 1 hour, and then the crystals were collected, subjected to slurry washing twice with 150 ml of water and twice with 150 ml of hexane, and dried at 60°C under reduced pressure for 2 hours to obtain the subject material. Amount obtained 19.5 g (yield 94%).

1H-NMR (CDCI3, δ, ppm): 5.48(2H, s), 7.12(1H, td), 7.34(1H, d), 7.77(1H, dd), 7.96(1H, m), 8.05(1H, dd), 8.45(1H, d), 8.56(1H, d)

MS: m/z - 332(M+H)

Synthetic Example 5: N-[1 -((6-chloropyridin-3-y1)methy!)pyridin-2(1 HJ-yiideneJ-2,2,2trifluoro-N'-methylacetimidamide (Compound 1-42) [Chemical Formula 50]

150 mg (0.45 mmol) of the N-[1-((6-chloropyrldin-3-yt)methyl)pyridln-2(1H)-ylidene]-

2,2,2-trifluoroethanethloamlde (1-20) synthesized by the method in Synthetic Example 4 was dissolved in 5 ml of methanol, 105 μΙ (42 mg, 1.36 mmol) of methylamine (40% methanol solution) and 124 mg (0.45 mmol) of silver carbonate were added thereto, and the resulting mixture was stirred at 50°C for 1 hour. After the reaction was completed, the réaction solution was retumed to room température and subjected to suction filtration by using celite to remove Insoluble materials. Ethyl acetate and water were added thereto to perform liquid séparation, and the organic layer was dried over anhydrous magnésium sulfate, then concentrated under reduced pressure and purified with silica gel column chromatography (hexane: ethyl acetate = 1:1) to obtain the subject material. Amount obtained 81 mg (yield 56%).

235

Synthetic Example 6: N’-(aryloxy)-N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)y1idene]-2,2,2-trifluoroacetimidamide (Compound 1-507) [Chemical Formula 51J a

ⁿoch₂ch-ch_z mg (0.09 mmol) of the N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylÎdenel-2,2,2trifluoroethanethioamide (1-20) synthesized by the method in Synthetic Example 4 was dissolved In 5 ml of éthanol, 50 mg (0.45 mmol) of O-ally hydroxylamine hydrochloride, 62 μΐ (0.45 mmol, 45 mg) of triethylamlne and 25 mg (0.09 mmol) of sllver carbonate were added thereto, and the resulting mixture was stirred at 50°C for 5 hours and 20 minutes. After the reaction was completed, the reaction solution was retumed to room température to filter off Insoluble materials. The filtrate was concentrated under reduced pressure to perform liquid séparation with ethyl acetate and 1% hydrochloric acid, then the ethyl acetate layer was washed with a saturated saline solution, and dried over anhydrous magnésium sulfate and then concentrated under reduced pressure. The ethyl acetate layer was purified by a TLC plate (one sheet of 0.5 mm plate, evolved with hexane: ethyl acetate - 1:1 ) to obtain the subject material. Amount obtained 15 mg (yield 45%).

Synthetic Example 7: N-[1-((6-chloropyridin-3-y1)methy1)pyridin-2(1H)-ylideneI-2,2,2trifluoro-N*-hydroxyacetimidamide (Compound 1-499} [Chemical Formula 52[

ml of éthanol was added to 1.00 g (3.00 mmol) of the N-[1-((6-chloropyridin-3y1)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroethanethioamide (1-20) 1 synthesized by the method In Synthetic Example 4,1.04 g (15.0 mmol) of hydroxylamine hydrochloride and 2.00

236 ml (1.50 g, 15.0 mmol) of triethylamine were added thereto In sequence, and the resulting mixture was stirred at 50°C for 21.5 hours. After the reaction was completed, ethyl acetate and 1% hydrochloric acid were added to the reaction solution to perform liquid séparation, and the organic layer was washed with water, dried over anhydrous magnésium sulfate and concentrated under reduced pressure. The organic layer was purified by silica gel column chromatography (hexane: ethyl acetate = 1:1) to obtain the subject material. Amount obtained 625 mg (yield 63%).

Synthetic Example 8: N-(benzoyloxy)-N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)ylideneJ-2,2,2-trifluoroacetimldamide (Compound 1-519) [Chemical Formula 53]

mg (0.09 mmol) ofthe N-[1-((6-chloropyridin-3-yl)methyl}pyridin-2(1H)-ylidene]-2,2,2trifluoro-N'-hydroxyacetimidamide (1-499) synthesized by the method in Synthetic Example 7 was dissoived in 3 ml of anhydrous acetonitrile, 24 μΙ (17 mg, 0.17 mmol) of triethylamine and 20 μg (22 mg, 0.17 mmol) of benzoyl chloride were added thereto in sequence, and the resulting mixture was stirred at room température for 10 minutes. After the reaction was completed, ethyl acetate and 1% hydrochloric acid were added to the reaction solution to perform liquid séparation, and the organic layer was washed with water, dried over anhydrous magnésium sulfate and concentrated under reduced pressure. The organic layer was purified by a TLC plate (one sheet of 0.5 mm plate, evolved with hexane: ethyl acetate = 1:1) to obtain the subject material. Amount obtained 26 mg (yield 67%).

Synthetic Example 9: N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2trifluoro-N'-((propylcarbamoyl}oxy)acetimidamide (Compound 1-534)

237 [Chemical Formula 54]

ml of anhydrous acetonitrile was added to 11 mg (0.13 mmol) of normal propyi isocyanate, 40 mg (0.12 mmol) ofthe N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]·

2,2,2-trifluoro-N^,-hydroxyacetimidamide (1-499) synthesized by the method In Synthetic Example 7 and 4 mg (0.04 mmol) of potasslum-t-butoxlde were added thereto, and the resulting mixture was stirred at room température for 1 hour. After the reaction was completed, the reaction solution was concentrated under reduced pressure, and ethyi acetate and a saturated saline solution were added thereto to perform liquid séparation. The ethyi acetate layer was dried over anhydrous magnésium sulfate, concentrated under reduced pressure and purified by a TLC plate (one sheet of 0.5 mm plate, evolved with hexane: ethyi acetate = 1:3) to obtain the subject material. Amount obtained 16 mg (yield 32%).

Synthetic Example 10: Diisopropyl 1-((6-chloropyridin-3-yl)methyl)pyridyn-2(1H)ylidenphospholamide trithioate (Compound 1-702) [Chemical Formula 55]

Cl

4.0g (15.7mmol)of 1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H) imlne hydrochloride obtained by the above-described method was suspended in

24.6ml of dichloromethane, and under ice-cooiing 1.35ml of phosphorpus trichlorlde over 10mins, following 3.16g(31.2mmol) of triethylamine dissolved in

238

37ml of dichloromethane was added thereto. Afetr the mixture was stirred for 2 hours at room température, 499mg(15.6mmol)of sulfur was added to the mixture, and the mixture was stirred over night at room température. Under ice-coollng 3.16g(31.2mmol) of triethylamine, following 2.38g(31.2mmoi) of 2-propanethioi dissolved In 10ml of dichloromethane were added to the mixture, addltionary the mixture was stirred for a day. After the reaction was completed, the reaction solution was concentrated under reduced pressure, and was extracted by 100ml of diethylether twice. The ether solution was concentrated under reduced pressure, and 2.49g of cruede compounds was obtained. 186mg of crude compound was purified by a TLC plate (5 sheets of 0.5 mm plate, evolved with ethyl acetate ) to obtain the subject material(47mg. yield 9%) and (1-((6-chioropyridin-3-yl)methyl)pyridin-2(1H)-ylidene)phosphoramidothioic dichloride (19mg.yield 5%).

[Chemical Formula 56]

Cl

(1-((6-chioropyridln-3-yi)methyl)pyrldln-2(1H)ylldene)phosphoramidothioic dichloride

Synthetic Example 11: N-[1-((6-chioropyridln-3-yl)methyl)pyrldin-2(1H)ylidene]-1,1,1-trlfluoromethanesulfinamide (Compound1-703) [Chemical Formula 57]

Cl

330mg(2mmol) of sodium trifluoromethanesuifonate was added by 2ml of

II

239 ethyiacetate and 154mg(1mmol) of phosphorus oxychloride and stlired for 5min at room tempreture. And 220mg (0.86mmol)of 1-((6-chloropyridin-3yi)methyi)pyridin-2(1H)-imine hydrochloride obtained by the above-described method was added to the mixture, and stiired for 2 hours. After the reaction was completed, the reaction mixture waas purified by silica-gel couium chromatographyfeluent ethyiacetate :hexane=1:1) to obtain the subject materlal(115mg. yieid 39%)

The compounds shown in the following Table were prepared by the method in accordance with Synthetic Examples 1 to 11.

240

ITable 42-1]

Compound No.	Raw material 1	Raw material 2	Base and the like	Solvent	Reaction température, Time	Method (Table)	Yield (%)
266-2	69 mg (0.43 mmol) of 2-chloro-5(chloromethyl)pyridine	84 mg (0.43 mmol) of 2,2,2trifluoro-N-(1,3,4-thiadiazol2(3H)-ylidene))acetamide	71 mg (0.52 mmol) of potassium carbonate	Acetonitrile	reflux, 20h	A	32
444-2	56 mg (0.41 mmol) of 2-chloro-5(chloromethyl)thiazole	66 mg (0.34 mmol) of 2,2,2trifluoro-N-(1,3,4-thiadiazol2(3H)-ylidene))acetamide	56 mg (0.41 mmol) of potassium carbonate	Acetonitrile	reflux, 20h	A	21
190-2	71 mg (0.27 mmol) of 1-((6chloropyridin-3yl)methyl)pyrimidin-2(1 H)-imine hydrochloride	53 μΙ (0.38 mmol) of anhydrous trifluoroacetic acid	53 μΙ (0.38 mmol) of triethylamine	Dichloromethane	Room température, 1 h	B	28
201-2	120 mg (0.47mmol) of 1-((6chloropyridin-3yl)methyl)pyrazin-2(1 H)-imine hydrochloride	99 μΙ (0.71 mmol) of anhydrous trifluoroacetic acid	160 μΙ (1.17 mmol) of triethylamine	Dichloromethane	Room température, 30 min	B	11

[Table 42-2]

223- 2	530 mg (2.07 mmol) of 2-chloro-2-((6chloropyridin-3-yl)methyl)pyridazin3(2H)-imine hydrochloride	390 μΙ (2.79 mmol) of anhydrous trifluoroacetic acid	537 μΙ (2.79 mmol) of triethylamine	Dichloromethane	Room température, 2h	B	14
146- 2	113 mg (0.70 mmol) of 2-chloro-5(chloromethyl)pyridine	145 mg (0.70 mmol) of 2,2,2trifluoro-N-(3-hydroxypyridin-2( 1H)ylidene))acetamide	116 mg (0.84 mmol) of potassium carbonate	Acetonitrile	reflux, 13h	A	15
224- 2	190 mg (0.73 mmol) of 2-((2chlorothiazol-5-yl)methyl)pyridazin-3(2H)imine hydrochloride	168 μΙ (1.20 mmol) of anhydrous trifluoroacetic acid	220 μΙ( 1.60 mmol) of triethylamine	Dichloromethane	Room température, 5 min	B	16
102- 2	116 mg (0.72 mmol) of 2-chloro-5(chloromethyl)pyridine	155 mg (0.72 mmol) of N-(3cyanopyridin-2( 1 H)-ylidene))2,2,2-	109 mg (0.79 mmol) of potassium	Acetonitrile	reflux, 8h	A	22

241

		trifluoroacetamide	carbonate
212- 2	59 mg (0.37 mmol) of 2-chloro-5(chloromethyl)pyridine	70 mg (0.37 mmol) of 2,2,2trifluoro-N-(pyrimidin-4(3H)ylidene))acetamide	55 mg (0.40 mmol) of potassium carbonate	Acetonitrile	reflux, 7h	A	32

[Table 42-3]

1-20	20.0 g (63.4 mmol) of N-[1-((6-chloropyridin-3yl)methy!)pyridin-2(1H)-ylidene]-2,2,2trifluoroacetamide	16.3 g (36.7 mmol) of phosphorus pentasulfide	6.72 mg (63.4 mmol) of sodium carbonate	Toluene	50°C, 19h	D	94
12-2	78 mg (0.38 mmol) of 2-chloro-4(bromomethyl)pyridine	73 mg (0.38 mmol) of 2,2,2-trifluoro-N(pyridin-2(1 H)-ylidene))acetamide	58 mg (0.42 mmol) of potassium carbonate	Acetonitrile	reflux, 3.5h	A	44
213- 2	79 mg (0.47 mmol) of 2-chloro-5(chloromethyl)thiazole	90 mg (0.47 mmol) of 2,2,2-trifluoro-N(pyrimidin-4(3H)-ylidene))acetamide	72 mg (0.52 mmol) of potassium carbonate	Acetonitrile	reflux, 12h	A	42
1-17	150 mg (0.66 mmol) of 1-[(6-chloropyridin-3y1)methy1]pyridin-2(1 H)-imine hydrochloride	177 mg (0.66 mmol) of 4nitrophenyl(2,2,2trifluoroethyi)carbamate	200 mg (1.46 mmol) of potassium carbonate	Acetonitrile	50°C, 2h	C	21
1-18	150 mg (0.66 mmol) of 1-[(6-chloropyridin-3y1)methy1]pyridin-2(1 H)-imine hydrochloride	184 mg (0.66 mmol) of 4nitrophenyl( 1,1,1 -trifluoropropa n-2yl)carbamate	200 mg (1.46 mmol) of potassium carbonate	Acetonitrile	50°C, 2h	C	30

[Table 42-4]

119	150 mg (0.66 mmol) of 1-[(6chloropyridin-3-y1)methyl]pyridin2(1H)-imine hydrochloride	220 mg (0.66 mmol) of 1,1,1,3,3,3-hexafluoropropan-2yl(4-nitropheny1)carbamate	200 mg (1.46 mmol) of potassium carbonate	Acetonitrile	50°C, 3h	C	27
7- 2	116 mg (0.72 mmol) of 2-chloro-5(chloromethyl)pyrazine	137 mg (0.72 mmol) of 2,2,2trifluoro-N-(pyridin-2(1 H)ylidene))acetamide	110 mg (0.80 mmoljof potassium carbonate	Acetonitrile	reflux, 5h	A	49
113	200 mg (0.78 mmol) of 1-[(6chloropyridin-3-y1)methyl]pyridin2(1H)-imine hydrochloride	103 μΙ (1.17 mmol) of 2,2,2trifluoropropionic acid	EDC- HCI225mg(1.17mmol), DMAP238mg(1.95 mmol)	Dichloromethane	Room température, 12h	B	21

242 [Table 43-1]

Compound No.	Raw material 1	Raw material 2	Base and the like	Solvent	Reaction température, Time	Method (Table)	Yieid (%)
168-2	273 mg (1.70 mmol) of 2-chloro-5(chloromethyl)pyridine	350 mg (1.70 mmol) of 2,2,2trifluoro-N-(5-hydroxypyridin2(1 H)-ylidene))acetamide	248 mg(1.80 mmol) of potassium carbonate	DMF	65°C, 2h	A	15
1-21	23 mg (0.077 mmol) of N-[1-{(6chloropyridin-3-yl)methyl)pyridin2(1H)-ylidene]-2,2difluoroacetamide	41 mg (0.092 mmol) of phosphorus pentasulfide	10 mg (0.092 mmol) of sodium carbonate	THF	Room température, 2 h	D	49
3-20	30 mg (0.10 mmol) of N-[1 -((6fluoropyridin-3-yl)methyl)pyridin2(1H)-ylidene]-2,2,2trifluoroacetamide	49 mg (0.11 mmol)of phosphorus pentasulfide	12 mg (0.11 mmol) of sodium carbonate	THF	Room température, 3 h	D	49
4-20	30 mg (0.083 mmol) of N-[1-{(6bromopyridin-3-yl)methyl)pyridin2(1H)-ylidene]-2,2.2trtfluoroacetamlde	41 mg (0.09 mmol) of phosphorus pentasulfide	10 mg (0.09 mmol) of sodium carbonate	THF	Room température, 3 h	D	61

[Table 43-2]

3-3	116 mg (0.72 mmol) of 2-fluoro-5(bromomethyl)pyridine	116 mg (0.68 mmol) of 2,2difluoro-N-{pyridin-2(1 H)ylidene))acetamide	110 mg (0.80 mmol) of potassium carbonate	Acetonitrile	reflux, 6h	A	27
4-3	50 mg (0.20 mmol) of 2-bromo-5(bromomethyl)pyridine	35 mg (0.20 mmol) of 2,2difluoro-N-(pyridin-2(1 H)ylidene))acetamide	33 mg (0.24 mmol) of potassium carbonate	Acetonitrile	reflux, 6h	A	53
5-5	46 mq (0.21 mmol) of 5-	50 mg (0.21 mmol) of	35 mg (0.25	Acetonitrile	reflux, 2h	A	26

243

	(bromomethyl)-2-chloro-3fluoropyridine	2,2,3,3,3-pentafluoro-N(pyridtn-2(1H)ylidene))propanamide	mmol) of potassium carbonate
6-5	43 mg (0.21 mmol) of 5(bromomethyl)-2-chloropyrimidine	50 mg (0.21 mmol) of 2,2,3,3,3-pentafluoro-N(pyridin-2(1H)yHdene))propanamide	35 mg (0.25 mmol) of potassium carbonate	Acetonitrile	reflux, 2h	A	21
1-22	37 mg (0.11 mmol) of 2-chloro-N[1-((6-chloropyridin-3yl)methyl)pyridin-2(1 H)-ylidene]2,2-difluoroacetamide	49 mg (0.11 mmol)of phosphorus pentasulfide	12 mg (0.11 mmol) of sodium carbonate	THF	Room température, 4 h	D	31
1-23	31 mg (0.085 mmol) of N-[1-((6chloropyridin-3-yI)methyl)pyridin2(1H)-ylidene]-2,2,3,3,3pentafluoropropanamide	38 mg (0.085 mmol) of phosphorus pentasulfide	9 mg (0.0854 mmol) of sodium carbonate	THF	Room température, 4 h	D	59

[Table 43-3]

5-20	36 mg (0.11 mmol) of N-[1-((6chloro-5-fluoropyridin-3yf )methyl)pyridin-2( 1H )-yfidene]2,2,2-trifl uoroa cetamide	49 mg (0.11 mmol) of phosphorus pentasulfide	12 mg (0.11 mmol) of sodium carbonate	THF	Room température, 4 h	D	100
5-3	65 mg (0.29 mmol) of 5(bromomethyl)-2-chloro-3fluoropyridine	50 mg (0.29 mmol) of 2,2difluoro-N-(pyridin-2(1 H)y1idene))a cetamide	48 mg (0.35 mmol) of potassium carbonate	Acetonitrile	reflux, 3h	A	38
6-3	60 mg (0.29 mmol) of 5(bromomethyl)-2-chloropyrimidine	50 mg (0.29 mmol) of 2,2difl uoro- N-(pyri din-2( 1H )ylidene))acetamide	48 mg (0.35 mmol) of potassium carbonate	Acetonitrile	reflux, 3h	A	37
8-2	73 mg (0.45 mmol) of 3-chloro-6(chloromethyf)pyridazine	97 mg (0.51 mmol) of 2,2,2trifluoro-N-(pyridin-2(1 H)ylidene))acetamide	83 mg (0.60 mmol) of potassium carbonate	DMF	65°C,3h	A	32
5-4	54 mg (0.24 mmol) of 5(bromomethyl )-2-ch loro-3-	50 mg (0.24 mmol) of 2chloro-2,2-difluoro-N-(pyridin-	41 mg (0.30 mmol) of	Acetonitrile	reflux, 6h	A	51

244

	fluoropyridine	2(1 H)-y!idene))acetamide	potassium carbonate
4-4	60 mg (0.24 mmol) of 2-bromo-5bromomethylpyridine	50 mg (0.24 mmol) of 2chloro-2,2-difIuoro-N-(pyridin2(1 H)-ytidene))acetamide	41 mg (0.30 mmol) of potassium carbonate	Acetonitrile	reflux, 6h	A	48

[Table 43-4]

6-4	49 mg (0.24 mmol) of 5(bromomethyl)-2-chloropyrimidine	50 mg (0.24 mmol) of 2chloro-2,2-difluoro-N-(pyridin2(1 H)-ylidene))acetamide	41 mg (0.30 mmol) of potassium carbonate	Acetonitrile	reflux, 6h	A	55
4-5	65 mg (0.26 mmol) of 2-bromo-5bromomethylpyridine	50 mg (0.26 mmol) of 2,2,3,3,3-pentafluoro-N(pyridin-2(1H)yl idene))propanamide	41 mg (0.30 mmol) of potassium carbonate	Acetonitrile	reflux, 2h	A	8

[Table 44-1]

Compound No.	Raw material 1	Raw material 2	Base and the like	Solvent	Reaction température, Time	Method (Table)	Yield (%)
2-20	70 mg (0.22 mmol) of N-[1-((2chlorothiazol-5-yl)methyl)pyridin2(1H)-ylidene]-2,2,2trifluoroacetamide	107 mg (0.24 mmol) of phosphores pentasulfide	25 mg (0.24 mmol) of sodium carbonate	THF	Room température, 4 h	D	11
10-20	130 mg (0.37 mmol) of 2,2,2trifluoro-N-[1-((6trifluoromethyi)pyridin-3yl)methyl)pyridin-2(1H)-y!idene]acetamide	181 mg (0.41 mmol)of phosphores pentasulfide	43 mg (0.41 mmol) of sodium carbonate	THF	Room température, 4 h	D	93
3-4	110 mg (0.58 mmol) of 2-fluoro-5(bromomethyl)pyridine	105 mg (0.51 mmol) of 2chloro-2,2-difluoro-N-	103 mg (0.75 mmol) of	DMF	65°C, 2h	A	63

245

		(pyridin-2(1H)ylidene))acetamide	potassium carbonate
3-5	110 mg (0.58 mmol) of 2-fluoro-5(bromomethyl)pyridine	139 mg (0.58 mmol) of 2,2,3,3,3-pentafIuoro-N(pyridin-2(1H)ylidene)propanamide	88 mg (0.63 mmol) of potassium carbonate	DMF	65°C, 2h	A	22

(Table 44-2]

11-20	40 mg (0.15 mmol) of 2,2,2trifluoro-N-[1-((tetrahydrofuran-3yl)methyl)pyridin-2(1 H)ylidenelacetamide	65 mg (0.11 mmol) of phosphorus pentasulfide	16 mg (0.15 mmol) of sodium carbonate	THF	Room température, 4 h	D	53
1-14	200 mg (0.78 mmol) of 1-((6chloropyridin-3-yl)methyl]pyridin2(1H)-imine hydrochloride	76 μΙ (0.94 mmol) of acrylic acid chloride	32 μΙ (0.23 mmol) of triethylamine	Acetonitrile	reflux, 1h	B	28
1-37	78 mg (0.28 mmol) of N-[1-((6chloropyridin-3-yl)methyl)pyridin2(1 H)-ylidene]-propionamide	125 mg (0.28 mmol) of phosphorus pentasulfide	30 mg (0.28 mmol) of sodium carbonate	THF	Room température, 2 h	D	21
1-39	180 mg (0.96 mmol) of N-[1-((6chloropyridin-3-yl)methyl)pyridin2( 1 H)-ylidene]-isobutyramide	341 mg (0.75 mmol) of phosphorus pentasulfide	102 mg (0.96 mmol) of sodium carbonate	THF	Room température, 2 h	D	29
1-40	54 mg (0.19 mmol) of N-[1 -((6chloropyridin-3-yl)methyl)pyridin2(1 H)-ylidene]-cyclopropane carboxyamide	54 mg (0.19 mmoljof phosphorus pentasulfide	20 mg (0.19 mmol) of sodium carbonate	THF	Room température, 2 h	D	12

246 (Table 44-3]

1-15	200 mg (0.78 mmol) of 1-1(6chloropyridin-3-yl)methyl]pyridin2(1H)-imine hydrochloride	83 mg (0.94 mmol) of propyol oxychloride	320 μΐ (2.34 mmol) of triethylamine	Acetonîtrile	reflux, 5h	B	19
1-35	26 mg (0.074 mmol) of Ν-]1-((θchloropyridin-3-yl )methyl )pyridin2(1H)-ylidene]-3phyenylpropanamide	26 mg (0.06 mmol) of phosphores pentasulfide	8 mg (0.074 mmol) of sodium carbonate	THF	Room température, 1.5 h	D	23
1-501	N-[1-((6-chloropyridin-3yl)methyl)pyridin-2(1H)-ylidene]2,2,2-trifluoroethanethioamide	145 mg (1.50 mmol)of Oethyl hydroxylamïne hydrochloride	205 μΙ (1.50 mmol) of triethylamine	Ethanol	50°C, 19.5h	F	14
1-499	N-]1 -((6-chloropyridin-3yl)methyl)pyridin-2(1 H)-ylidene]2.2.2-trifluoroethanethioamide	1.04 g (15.0 mmol) of hydroxylamïne hydrochloride	2.00 ml (15.0 mmol) of triethylamine	Ethanol	50°C, 21 h	F	63
1-510	N-[1 -((6-chloropyridîn-3yl)methyl)pyridin-2(1 H)-ylidene]2,2,2-trifluoroethanethioamide	239 mg (1.50 mmol) of Obenzyl hydroxylamïne hydrochloride	205 μΙ (1.50 mmol) of triethylamine	Ethanol	50°C, 19.5h	F	20

(Table 44-4]

1-151

30 mg (0.09 mmol) of N-[1-((6chloropyridin-3-yl)methyl)pyridin2( 1 H)-ylidene]-2, â^-trifluoro-N'hydroxyacetimidamide

20 μΙ (0.28 mmol) of acetyl chioride

38 μΙ (0.28 mmol) of triethylamine

Acetonîtrile

Room température, 15 min

G

72

247 [Table 45-1]

Compound No.	Raw material 1	Raw material 2	Base and the like	Solvent	Reaction température, Time	Method (Table)	Yield (%)
1-519	30 mg (0.09 mmol) of N-[1-((6chloropyridin-3-yl)m ethyî)pyridin-2( 1H )ylidene]-2,2₁2-trifluoro-N’hydroxyacetimidamide	20 μΙ (0.17 mmol) of benzoyl chloride	24 μ\| (0.17 mmol) of triethylamine	Acetonitrile	Room température, 10 min	G	67
1-523	30 mg (0.09 mmol) of N-[1-((6chloropyridin-3-yl)methyl)pyridin-2( 1H)yüdene]-2,2,2-trifïuoro-N'hyd roxya cetimida mide	20 μΙ (0.26 mmol) of methyl chloroformate	36 μΙ (0.26 mmol) of triethylamine	Acetonitrile	Room température, 20 min	G	49
1-528	30 mg (0.09 mmol) of N-[1-((6chloropyridin-3-yl)methy!)pyridÎn-2(1 H)y!idene]-2,2,2-trifluoro-N'hyd roxya cetimidam ide	20 μΙ (0.18 mmol) of methanesulfonyl chloride	25 μΙ (0.18 mmol) of triethylamine	Acetonitrile	Room température, 20 min	G	100

[Table 45-2]

1-531	30 mg (0.09 mmol) of N-[1-((6chloropyridin-3yl)methyl)pyridin-2(1 H)ytideneJ^.Z^-trifluoro-N’hyd roxya cetimidamide	28 mg (0.15 mmol) of 4methylbenzenesufonyl chloride	21 μΙ (0.15 mmol) of triethylamine	Acetonitrile	Room température, 12 h	G	100
1-507	30 mg (0.09 mmol) of N-[1((6-chloropyridin-3yl)methy!)pyridin-2(1 H)ytidenej-2,2,2trifluoroethanethioamlde	50 mg (0.45 mmol) of O-allyl hydroxylamine hydrochloride	62 μΙ (0.45 mmol) of triethylamine, 25 mg (0.09 mmol) of silver carbonate	Ethanol	50°C, 5h	F	45
1-516	30 mg (0.09 mmol) of N-[1-((6chloropyridin-3y!)methy!)pyridin-2{1 H)ylidenel-^^^-trifluoro-N’-	20 μΙ (0.25 mmol) of acryloyl chloride	34 μΙ (0.25 mmol) of triethylamine	Acetonitrile	Room température, 20 min	G	64

248

	hydroxyacetimidamide
1-518	30 mg (0.09 mmol) of N-[1-((6chloropyridin-3yl)methyl)pyridin-2( 1H)ylidene]-2,2,2-trifluoro-N’hydroxyacetimidamide	15 mg (0.18 mmol)of 3-butynoate	EDC- HCl135mg(0.18mm ol). DMAP22mg(0.18 mmol)	Dichloromethane	Room température, 21 h	G	22

[Table 45-3]

1-527	30 mg (0.09 mmol) of N-[1-((6chloropyridin-3yl)methyl)pyridin-2( 1H)ylidene]-2,2,2-trifluoro-N’hydroxyacetimidamide	20 μΙ (0.16 mmol) of phen^ chloroformate	22 μΙ (0.16 mmol) of triethylamine	Acetonitrile	Room température, 1.5 h	G	54
1-521	30 mg (0.09 mmol) of N-[1-((6chloropyridin-3yl)methyl)pyridin-2(1H)ylidene]-2,2,2-trifluoro-N*hydroxyacetimidamide	20 mg (0.14 mmol)of nicotinic acid chloride hydrochloride	40 μΙ (0.28 mmol) of triethylamine	Acetonitrile	Room température, 1.5 h	G	46
1-43	100 mg (0.30 mmol) of N-[1 ((6-chloropyridi n-3yt)methyl)pyridin-2(1 H)ylidene]-2,2,2trifluoroethanethioamide	Ethylamine (30% methanol solution, 0.60 mmol)	90 μΙ (0.60 mmol) of triethylamine, 91 mg (0.33 mmol) of silver carbonate	Ethanol	50°C, 1.5h	E	57
1-536	50 mg (0.15 mmol) of N-[1-((6chloropyridin-3- yf )methyt) pyridîn-2( 1H)ylidene]-2,2,2-trifluoro-N*hydroxyacetimidamide	20 μΙ (0.17 mmol)of benzyl isocyanate	tBuOK 5mg(0.04mmol)	Acetonitrile	Room température, 1 h	H	30

[Table 46-1]

249

Compound No.	Raw material 1	Raw material 2	Base and the like	Solvent	Reaction température, Time	Method (Table)	Yield (%)
1-42	150 mg (0.45 mmol) of Ν-[1-((βchloropyridin-3-yl)methyi)pyridin-2(1 H)ylidene]-2_t2,2-trifluoroethanethioamide	Methylamine (40% methanol solution, 1.36 mmol)	124 mg (0.45 mmol) of silver carbonate	Methanol	50°C, 1h	E	56
1-500	50 mg (0.15 mmol) of N-[1-{(6chloropyridin-3-y1)methyi)pyridin-2(1 H)y1idene]-2,2,2-trifluoroethanethioamide	63 mg (0.75 mmol) of O-methyl hydroxylamine hydrochloride	103 μΐ (0.75 mmol)of triethylamine, 41 mg (0.15 mmol) of silver carbonate	Ethanol	50°C, 5h	F	50
1-504	50 mg (0.15 mmol) of N-[1-((6chloropyridin-3-yi)methyl)pyridin-2( 1H)yiidene]-2,2,2-trtfluoroethanethioamide	95 mg (0.75 mmol) of O-t-butyl hydroxylamine hydrochloride	165 μΐ (1.20 mmoljof triethylamine, 62 mg (0.23 mmol) of silver carbonate	Ethanol	50°C, 5h	F	19

[Table 46-2]

1-534	40 mg (0.12 mmol) of N-[1-{(6chloropyridin-3-yl)methyl)pyridin2( 1 H)-ylïdene]-2_t2,2-trifluoro-N’hydroxyacetimidamide	11 mg (0.13 mmol) of n-propyi isocyanate	tBuOK4mg(0.04mmol )	Acetonitrile	Room température, 1h	H	32
1-535	40 mg (0.12 mmol) of N-[1 -((6chloropyridin-3-yi)methy1)pyridin2(1 H)-ylidene]-2,2_t2-trifluoro-N'hydroxyacetimidamide	14 mg (0.13 mmol) of chloroethyi isocyanate	tBuOK4mg(0.04mmol )	Acetonitrile	Room température, 1h	H	54
1-72	150 mg (0.45 mmol) of N-[1-((6chloropyridin-3-yl)methyi)pyridin2(1H)-yiidene]-2,2,2trifluoroethanethioamide	74 μΐ (0.68 mmol) of benzylamine	137 mg (0.50 mmol) of silver carbonate	Ethanol	50°C, 3h	E	45

250 [Table 46-3]

1-150	100 mg (0.30 mmol) of N-[1-((6chloropyridin-3-yl)rnethyl)pyridin2(1H)-ylidene]-2,2,2trifluoroethanethioamide	56 μΙ (0.60 mmol) of m ethytthioethyla min e	91 mg (0.33 mmol) of silver carbonate	Ethanol	50°C, 5h	E	50
1-67	100 mg (0.30 mmol) of N-[1-{(6chloropyridin-3-yl)methyl)pyridin2(1 H)-y1idene]-2,2,2trifluoroethanethioamide	74 μΙ (1.20 mmol) of 2-aminoethanol	91 mg (0.33 mmol) of silver carbonate	Ethanol	50°C, 2h	E	49
1-515	30 mg (0.09 mmol) of Ν-[1-((θchloropyridin-3-yl)methyt)pyridin2(1 H)-ylidene]-2,2_t2-trifluoro-N’hydroxyacetimidamlde	40 μΙ (0.44 mmol) of cyclopropanecarbo xylic acid chloride	30 μΙ (0.22 mmol) of triethylamine	Acetonitrile	50°C, 2h	G	67

[Table 46-4]

1-56	100 mg (0.30 mmol) of N-[14(6chloropyridin-3-y1)methyt)pyridin2(1H)-y1idene]-2,2,2trifluorœthanethîoamide	38 μΙ (0.60 mmol) of propargylamine	91 mg (0.33 mmol) of silver carbonate	Ethanol	50°C, 2h -> reflux, 2h	E	57
1-512	30 mg (0.09 mmol) of N-[14(6chloropyridin-3-y1)methyl)pyridin2(1 H)-y1idene]-2,2,2-trifluoro-N'hydroxyacetimidamide	20 μΙ (0.23 mmol) of propionyl chloride	34 μΙ (0.25 mmol) of triethylamine	Acetonitrile	Room température, 30 min	G	32
1-514	30 mg (0.09 mmol) of N-[14(θchloropyridin-3-yt)methyl)pyridin2( 1 H)-y1idene]-2,2,2-trifluoro-N’hydroxyacetimidamide	20 μΙ (0.19 mmol) of isopropionyl chloride	27 μΙ (0.20 mmol) of triethylamine	Acetonitrile	Room température, 2h	G	61

251 [Table 46-5]

1-50

100 mg (0.30 mmol) of N-[1-((6chloropyridin-3-yl)methyl)pyridin2(1H)-yfidene]-2,2,2trifluoroethanethioamide

48 μΐ (1.20 mmol) of cyclopropylamine

91 mg (0.33 mmol) of silver carbonate

Ethanol

50°C, 1.5h-> reflux,4.5h

E

44

[Table 47-1]

Compound No.	Raw material 1	Raw material 2	Base and the like	Solvent	Reaction température, Time	Method (Table)	Yield (%)
1-114	80 mg (0.30 mmol) of N-[1-<(6chloropyridin-3-yl)methyl)pyridin2(1H)-ylidene]-2,2.2trîfluoroethanethioamide	48 μΐ (0.36 mmol) of 2phenyloxyethylamine	73 mg (0.33 mmol) of silver carbonate	Ethanol	50°C, 3.5h	E	52
1-44	80 mg (0.30 mmol) of N-[1-((6chîoropyridin-3-yl)methyl)pyridin2(1H)-ylidene]-2,2,2trifluoroethanethioamide	60 μΐ (0.72 mmol) of npropylamine	73 mg (0.33 mmol) of silver carbonate	Ethanol	50°C, 2h	E	55
1-118	100 mg (0.30 mmol) of N-[1-((6chîoropyridin-3-yl)methyl)pyridin2(1H)-ylidene]-2,2,2trifluoroethanethloamide	62 μΙ (0.60 mmol) of 2aminomethylpyridine	91 mg (0.33 mmol) of silver carbonate	Ethanol	50°C, 5h	E	70
1-119	100 mg (0.30 mmol) of N-[1-((6chloropyridin-3-yl)methyl)pyridin2(1H)-ylidene]-2,2,2trifluoroethanethioamide	62 μΙ (0.60 mmol) of 3aminomethylpyridine	91 mg (0.33 mmol) of silver carbonate	Ethanol	50°C, 5h	E	58

252 [Table 47-2]

1-47	100 mg (0.30 mmol) of N-[1 -((6chloropyridin-3-yl)methyl)pyridin2(1H)-ylidene]-2,2,2trtfluoroethanethioamide	44 mg (0.60 mmol) of nbutylamine	91 mg (0.33 mmol) of silver carbonate	Ethanol	50°C, 5h	E	49
1-55	100 mg (0.30 mmol) of N-[1-((6chloropyridin-3-yl)methyl)pyridin2(1H)-ylidene]-2,2,2trifluoroethanethioamide	CH2=CHCH2NH2 34mg (0.60m mol)	91 mg (0.33 mmol) of silver carbonate	Ethanol	50°C, 2h reflux, 1 h	E	53
1-122	100 mg (0.30 mmol) of N-[1-((6chloropyrid in-3-yl)methyl )pyridin2(1H)-ylidene]-2,2,2trifluoroethanethioamide	H2NCH2-(2-thienyl) 68mg(0.60mmol)	91 mg (0.33 mmol) of silver carbonate	Ethanol	50°C, 2h -> reflux, 1 h	E	30
1-45	100 mg (0.30 mmol) of N-[1-((6chloropyridin-3-yl)methyl)pyridÎn2(1H)-ylidene]-2,2,2trifluoroethanethioamide	70 mg (1.20 mmol)of isopropytamine	91 mg (0.33 mmol) of silver carbonate	Ethanol	50°C, 2h -> reflux,5h	E	35
1-124	100 mg (0.30 mmol) of N-[1-((6chloropyridin-3-yl)methyl)pyridin2(1H)-ylidene]-2,2,2trifluoroethanethioamide	H2NCH2-(2-furanyl) 58mg(0.60mmol)	91 mg (0.33 mmol) of silver carbonate	Ethanol	50°C, 2.5h	E	56

[Table 47-3]

1-126	100 mg (0.30 mmol) of N-[1-((6chloropyridin-3-yl)methyl)pyridin2(1H)-ylidene]-2,2,2trîfluoroethanethioamide	H2NCH2-(2thienyldrofuranyl) 61mg(0.60mmol)	91 mg (0.33 mmol) of silver carbonate	Ethanol	50°C, 1h	E	43
1-64	100 mg (0.30 mmol) of N-[1-((6chloropyridin-3-yl)methyl)pyridin2(1H)-ylidene]-2,2,2trifluoroethanethioamide	110 mg( 1.20 mmol)of aminoacetonitrile hydrochloride	91 mg (0.33 mmol) of silver carbonate	Ethanol	50°C, 1h-> reflux,6h	E	22

253

1-146	100 mg (0.30 mmol) of N-[1-((6chloropyridin-3-yl)methyl)pyridin2(1H)-ylidene]-2_t2,2trifluoroethanethioamide	CH3OCH2CH2NH2 45mg(0.60mmol)	91 mg (0.33 mmol) of silver carbonate	Ethanol	50°C, 5h	E	30
1-52	100 mg (0.30 mmol) of N-[1-((6chloropyridin-3-yl)methyl)pyridin2(1H)-ylidene]-2,2_t2trifluoroethanethioamide	51 mg (0.60 mmol) of cyclopentylamine	91 mg (0.33 mmol) of silver carbonate	Ethanol	50°C, 4h	E	30
1-121	100 mg (0.30 mmol) of N-[1-((6chloropyridin-3-yl)methyl)pyridin2(1H)-ylidenel-2,2_l2trifluoroethanethioamide	65 mg (0.60 mmol) of 4aminomethyl pyridine	91 mg (0.33 mmol) of silver carbonate	Ethanol	60°C. 4h	E	33

[Table 481

Compound No.	Raw material 1	Raw material 2	Base and the like	Solvent	Reaction température, Time	Method (Table)	Yield (%)
1-53	100 mg (0.30 mmol) of N-[1 -((6chloropyridin-3-yl)methyl)pyriclin2(1H)-ylidene]-2,2_t2trifluoroethanethioamide	59 mg (0.60 mmol) of cyclohexylamine	91 mg (0.33 mmol) of silver carbonate	Ethanol	60°C, 2h	E	28
1-76	100 mg (0.30 mmol) of N-[1-((6chloropyridin-3-yl)methyl)pyridin2(1H)-ylidenel-2,2,2trifluoroethanethioamide	73 mg (0.60 mmol) of phenethylamine	91 mg (0.33 mmol) of silver carbonate	Ethanol	60°C, 4h	E	60

254 [Table 49-1]

Compound No.	1H-NMR (CDCI3, 5, ppm)	MS or IR (KBr, v, cm'¹)
266-2	5.62 (2H, S), 7.33 (1H, d), 7.83 (1H, d), 8.57 (2H, m)	m/z = 323 (M+H)
444-2	5.73 (2H, s), 7.69 (1 H, s), 8.56 (1 H, s)	m/z = 329 (M+H)
190-2	5.39 (2H, s), 6.87 (1H, dd), 7.36 (1H, d), 7.91 (1 H. dd), 8,39 (1H, d), 8.49 (1H, s), 8.79 (1H, d)	m/z = 317 (M+H)
201-2	5.45 (2H, s), 7.37 (1H, d), 7.65 (1H, d), 7.87 (1H, dd), 7.99 (1 H, d), 8.49 (1H, d), 9.80 (1H, d)	m/z = 317 (M+H)
223-2	5.69 (2H, s), 7.31 (1H, d), 7.55 (1H, dd), 7.92 (1H, dd), 8.28 (1H, dd), 8.59 (1H, d), 8.78 (1H, dd)	m/z = 317 (M+H)
146-2	5.64 (2H, s), 7.14 (1H, dd), 7.33 (1H, d), 7.47 (1H, dd), 7.71 (1H, dd). 7.74 (1H, dd), 8.42 (1H, d), 11.64 (1H, brs)	m/z = 332 (M+H)
224-2	5.78 (2H, s), 7.57, 7.63 (1H, ddx2), 7.70 (1H, s), 8.26, 8.41 (1H, dd x 2), 8.82, 9.04 (1H, ddx2)	m/z = 323 (M+H)
102-2	5.56 (2H, s), 7.15 (1H, m), 7.38 (1H, d), 7.84 (1H, dd), 8.26 (1H, dd), 8.48 (1H, d), 8.60 (1H, d)	m/z - 341 (M+H)
212-2	5.43 (2H, S), 7.35 (1 H, d), 7.87 (1H, dd), 8.20 (1H, d), 8.29 (1H, d), 8.51 (1H, d), 8.77 (1H, s)	m/z = 317 (M+H)
1-20	5.48 (2H, s), 7.12 (1H, td), 7.34 (1H, d), 7.77 (1H, dd), 7.96 (1H, m), 8.05 (1H, dd), 8.45 (1H, d), 8.56 (1H, d)	m/z = 332 (M+H)
12-2	5.54 (2H, s), 6.96 (1H, m). 7.21 (1 H. d). 7.87 (1H, m), 7.97 (1 H, m), 8.34 (1H, d), 8.50 (1H, d) .....	m/z = 316 (M+H)
213-2	5.51 (2H, s), 7.69 (1H, s), 8.25 (1H, d), 8.30 (1H, d), 8.57 (1H, s)	m/z = 323 (M+H)

[Table 49-2]

1-17	4.52 (2H, q), 5.44 (2H, s), 6.85 (1H, td), 7.31 (1H, d), 7.57 (2H, m), 7.79 (1H, dd), 8.14 (1H, d), 8.40 (1 H, d)	m/z - 346 (M+H)
1-18	1.44 (3H, d), 5.31 (1H, m), 5.42 (2H, q), 6.54 (1H, td), 7.30 (1H, d), 7.53 (2H, m). 7.79 (1H, dd), 8.10 (1H, d), 8.40 (1H, d)	m/z = 360 (M+H)
1-19	5.47 (2H, s), 5.81 (1H, m), 6.69 (ÏH, m), 7.31 (1H, d). 7.65 (1H, m), 7.68 (1H, dd), 7.85 (1H, dd), 8.17 (1H, d), 8.40 (1H, d)	m/z = 414 (M+H)
7-2	5.57 (2H, s), 6.91 (1H, m), 7.80 (1H, m), 8.10 (1H, m), 8.47 (1H, s), 8.49 (1H, d), 8,72 (1H,

255 : i t > i .i ;

	d)
1-13	3.22 (2H, q), 5.46 (2H, s), 6.65 (1H, td), 7.31 (1H. d), 7.62 (1H, m), 7.66 (1H, dd). 7.70 (1H, dd), 8.35 (1H, d), 8.41 (1H, d)	m/s = 330 (M+H)
168-2	5.11 (2H, s), 7.40 (2H, m). 7.75 (1H, dd), 8.09 (1H, d), 8.15 (1H, d), 8.46 (1H, d), 8.81 (1 H. br s)	m/z = 332.0426 (M+H)
1-21	5.49 (2H, s), 6.21 (1H, t), 7.05 (1 H. td), 7.34 (1H, d), 7.82 (1 H. dd), 7.90 (1H, m), 7.94 (1H, dd), 8.45 (1H, d), 8.49 (1H, d)	m/z = 314.0346 (M+H)
3-20	5.51 (2H, s), 6.95 (1H, d), 7.15 (1H, td), 7.96 (2H, m), 8.09 (1H, d), 8.29 (1 H. d), 8.52 (1H, d)	m/z = 316.0559 (M+H)
4-20	5.47 (2H, s), 7.13 (1H. m), 7.50 (1H, m), 7.66 (1H. m), 7.97 (1H, m). 8.07 (1H, m), 8.43 (1H, s), 8.54 (1H, m)	m/z = 375.9 (M+H)
3-3	5.54 (2H, S). 5.92 (1H, t). 6.79 (1H, td), 6.94 (1H, dd), 7.70 (1H, m), 7.78 (1H, dd), 8.03 (1H, td), 8.30 (1H, d), 8.50 (1 H, d)
4-3	5.50 (2H, s), 5.90 (1H, t), 6.79 (1H, m), 7.48 (1H, d), 7.74 (3H, m), 8.43 (1H, d), 8.50 (1H, d)	m/z = 342 (M+H)
5-5	5.56 (2H, S), 6.91 (1H, m), 7.69 (1 H. dd), 7.82 (2H, m), 8.26 (1H, d), 8.60 (1 H, d)	m/z = 384.0372 (M+H)

[Table 49-3]

6-5	5.52 (2H. s), 6.93 (1H, m), 7.86 (2H, m). 8.61 (1H, d), 8.75 (2H, s)	m/z = 367.0687 (M+H)
1-22	5.49 (2H, s), 7.09 (1 H, td), 7.35 (1 H, d). 7.78 (1H, dd), 7.95 (2H, m), 8.46 (1H, d), 8.55 (1H, d)	m/z = 347.9972 (M+H)
1-23	5.47 (2H. s), 7.10 (1H, td), 7.34 (1H, d), 7.68 (1H. dd), 7.95 (2H, m), 8.41 (1H, d), 8.55 (1H. dd)	m/z = 382.0246 (M+H)
5-20	5.49 (2H, s), 7.10 (1H, m), 7.65 (1H, dd), 7.96 (1H. m), 8.00 (1H. m), 8.27 (1H, d), 8.63 (1H, d)	m/z = 350.0188 (M+H)
5-3	5.53 (2H, s), 5.90 (1H, t), 6.80 (1H, td), 7.76 (2H, m), 8.29 (1H, d), 8.52 ( 1 H. d)	m/z = 316.0507 (M+H)

256 [Table 50-1]

Compound No.	1H-NMR (CDCI3, δ, ppm)	MS or IR (KBr, v. cm’¹)
6-3	5.45 (2H, s), 5.89 (1H, t), 6.83 (1 H, td), 7.75 (1H. m), 7.82 (1H, dd). 8.52 (1H. d), 8.81 (2H. s)	m/z = 299.0532 (M+H)
8-2	5.73 (2H, s), 6.90 (1 H. td), 7.54 (1H, d), 7.81 (1 H. td), 7.97 (1H, d), 8.22 (1H. d), 8.53 (1H, d) .....
5-4	5.54 (2H, s), 6.86 (1H, td), 7.99 (3H, m). 8.30 (1H, d), 8.54 (1H, d)	m/z = 350.0082 (M+H)
4-4	5.52 (2H, s), 6.86 (1H, td), 7.49 (1H, d), 7.77 (2H, m), 7.83 (1H, dd), 8.45 (1H, d), 8.52 (1H, d)	m/z = 375.96 (M+H)
6-4	5.49 (2H. S), 6.90 (1 H, td). 7.82 (1H, td), 7.87 (1H, dd), 8.54 (1H, d), 8.81 (2H, s)	m/z = 333.0121 (M+H)
4-5	5.53 (2H, s), 6.89 (1H, td), 7.48 (1H, d), 7.70 (1H, dd), 7.82 (2H, m). 8.41 (1H, d), 8.58 (1H, d)	m/z = 410 (M+H)
2-20	5.57 (2H, s), 7.12 (1H. m), 7,68 (1H, s). 7.97 (1H, m), 8.12 (1 H, d), 8.67 (1H, d)	m/z = 338 (M+H)
10-20	5.58 (2H, s), 7.12 (1H. m), 7.70 (1H, d), 7.97 (2H, m), 8.02 (1H, d), 8.62 (1H, d), 8.77 (1H, s)	m/z = 366 (M+H)
3-4	5.55 (2H. S). 6.86 (1 H. td), 6.95 (1H. dd), 7.77 (1H, td), 7.85 (1H, dd), 8.06 (1H, td), 8.31 (1H, d), 8.53 (1H, d)	m/z = 316 (M+H)
3-5	5.56 (2H, s), 6.89 (1H, m), 6.94 (1H, dd), 7.80 (2H, m). 7,97 (1H. td), 8.27 (1H, d), 8.58 (1H. d)	m/z = 350 (M+H)
11-20	1.69 (1 H, m), 2.07 (1H, m), 2.84 (1H, m), 3.59 (1H, dd), 3.71 (1H, dd), 3.77 (1H, m), 3.96 (1H, m), 4.13 (1H, dd), 4.42 (1H. dd), 7.11 (1H, m), 7.92 (1H. dd), 7.98 (1H, m), 8.40 (1H, d)	m/z = 291 (M+H)

[Table 50-2]

1-14	5.44 (2H. s). 5.61 (1H, dd), 6.28 (1H, dd), 6.36 (1H, dd), 6.52 (1H, m). 7.30 (1H. d), 7.52 (1H, m), 7.57 (1H, d), 7.73 (1H, dd), 8.28 (1H, d), 8.44 (1H, d)	m/z = 274 (M+H)
1-37	1.28 (3H, t), 2.88 (2H, q), 5.41 (2H, s), 6.86 (1H, t), 7.35 (1H, d). 7.75 (3H. m), 8.10 (1H. d), 8.44 (1H, d)	m/z = 292 (M+H)
1-39	1,26 (6H, d), 2.55 (1H. m), 5.51 (2H, s), 6.98 (1H, m), 7.36 (1H, d), 7.76 (1H, dd), 7.77 (2H, m), 8.08 (1H, d), 8.44 (1H, d)	m/z = 306 (M+H)
1-40	0.92 (2H, m), 1.22 (2H, m), 2.40 (1H, m), 5.36 (2H, s), 6.77 (1H, td), 7.34 (1H, d), 7.66	m/z = 304 (M+H)

257

'.J'¹

	(2H, m), 7.71 (1H, dd), 8.14 (1H, d), 8.41 (1H, d)
1-15	5.08 (2H, d), 5.40 {2H, s), 5.84 {1H, t), 6.50 (1H. m), 7.30 (1H, d), 7.50 (1 H. m), 7.56 (1H. m), 7.80 (1H, dd), 8.25 (1 H, d), 8.47 (1 H, d)	m/z = 286 (M+H)
1-35	3.18 (4H, m), 5.05 (2H, s), 6.83 {1H, td), 7.05 (1H, t), 7.25 {2H, m), 7.38 (3H, m), 7.59 (1H. dd), 7.67 (1H. d). 7.72 (1H, td), 7.99 (1H, d), 8.30 (1H, d)	m/z = 368 (M+H)
1-501	1.20 (3H, t), 4.10 (2H, q), 5.22 (2H. s), 6.15 (1H, td), 6.27 (1H, d), 7.13 (1 H, m), 7.27 (2H, m), 7.79 (1H, dd), 8.37 (1H, d)	m/z - 359 (M+H)
1-499	5.26 (2H, s), 6.11 (1H, d), 6.31 (1H. m), 7.31 (1H, m). 7.50 (1H, d), 7.83 (1H, dd), 7.90 (1H, dd), 8.44 (1H, d), 11.0 (1H, s)	m/z = 331 (M+H)
1-510	5.07 (2H. s), 5.19 (2H, s), 6.13 (1 H, td), 6.22 (1H, d), 7.07 (1H, m), 7.18-7.40 (8H, m), 7.69 (1H, dd), 8.34 (1H, d)	m/z = 421 (M+H)
1-511	1.99 (3H, s), 5.27 (2H, s), 6.37 (2H, m), 7.31 (2H, m), 7.44 (1H, dd), 7.76 (1H, dd), 8.37 (1H. d)	m/z = 373 (M+H)
1-519	5.31 (2H, s), 6.36 {1 H. t), 6.51 (1H, d), 7.17 (1H, d), 7.25 (4H, m), 7.50 (3H, m), 7.78 (1 H, dd), 8.41 (1H, d)	m/z = 435 (M+H)

[Table 50-3)

1-523	3.84 (3H, S), 5.26 (2H, s), 6.35 (1H, m), 6.40 (1H, d), 7.30 (2H. m), 7.37 (1H, dd), 7.73 (1H, dd), 8.37 (1H, d)	m/z = 389 (M+H)
1-528	3.14 (3H, s), 5.27 (2H, s), 6.44 (1H, tdj, 6.54 (1H. dd), 7.32 (1H, d), 7.41 (2H, m), 7.68 (1H, dd), 8.39 (1H, d)	m/z = 409 (M+H)
1-531	2.45 (3H, s), 5.23 (2H. s), 6.37 (1 H. d), 6.42 (1H, td), 7.29 (4H, m). 7.45 (1H, d). 7.70 (1H, dd), 7.80 (2H, d), 8.35 (1H, d)	m/z = 485 (M+H)
1-507	4.54 (2H, m), 5.16 (2H. m), 5.22 (2H, s), 5.91 (1H, m). 6.17 (1 H. td), 6.29 (1H, d), 7.15 (1H, m), 7.27 (2H, m), 7.79 (1H, dd), 8.37 (1H,d)	m/z = 371 (M+H)

[Table 51-1]

Compou nd No.	1H-NMR (CDCI3, δ,ppm)	MS or IR \|KBr, v, cm*
1-516	5.27 (2H. s), 5.76 (1H, dd), 5.91 (1H, dd), 6.22 (1H, dd), 6.36 (1H, m), 6.42 (1H. d), 7.29 (2H, m), 7.42 (1H, d), 7.76 (1H, dd), 8.37 (1H, d)	m/z = 385 (M+H)
1-518	1.25 (1H. S). 1.98 (2H, s), 5.28 (2H. s), 6.38 (2H, m), 7.30 (2H, m), 7.41 (1H, d), 7.75 (1H, dd), 8.38 (1H, d)	m/z = 397 (M+H)

258

1-527	5.28 (2H, s), 6.39 (1H. m), 6.50 (1H, d), 7.13 (1H, d), 7.22-7.41 (7H, m), 7.76 (1H, dd), 8.40 (1 H, d)	m/z = 451 (M+H)
1-521	5.30 (2H, s), 6.42 (1H, t), 6.52 (1H, d), 7.20 (1H, d), 7.32 (2H, m), 7.53 (1H, dd), 7.75 (1H, dd), 8.01 (1 H, dd), 8.41 (1H, d), 8.54 (1H, d), 8.71 (1H, dd)	m/z = 436 (M+H)
1-43	1.13(3H, t), 3.03 (2H, q). 5.15 (2H. s), 6.12 (1 H, m), 6.19 (1H. d), 7.14(1H, m), 7.27 (1H, m), 7.33 (1H, d), 7.72 (1H. dd), 8.37 (1H, d)	m/z = 343 (M+H)
1-536	4.48 (2H, d), 5.25 (2H, s), 6.36 (1H, td), 6.41 (1H, d), 6.79 (1H, m), 7.41 (7H, m), 7.73 (1H, dd), 8.40 (1H, d)	m/z = 464 (M+H)
1-42	2.86 (3H, S), 5.16 (2H, s), 6.15 (2H, m), 7.16 (1H. m), 7.26 (1H, dd), 7.31 (1H, d), 7.73 (1H, dd), 8.38 (1H, d)	m/z = 329 (M+H)
1-500	3.86 (3H, s), 5.22 (2H, s), 6.17 (1H, m), 6.26 (1H, d), 7.14 (1H, m), 7.23 (1H. dd). 7.30 (1H, d), 7.78 (1H, dd), 8.39 (1H, d)	m/z = 345 (M+H)
1-504	1.23 (9H, s), 5.23 (2H, s), 6.10 (1H, m), 6.22 (1H, d), 7.09 (1H, m), 7.20 (1H, dd), 7.26 (1H. m), 7.79 (1H, dd), 8.35 (1 H. d)	m/z = 387 (M+H)
1-534	0.95 (3H, t), 1.61 (2H. m), 3.23 (2H, t), 5.24 (2H, s), 6.32 (1H. t), 6.39 (1H, d),6.48 (1H, m), 7.33 (3H, m), 7.74 ( 1 H. dd), 8.40 (1H, d)	m/z = 416 (M+H)

[Table 51-2]

1-535	3.65 (4H, m), 5.25 (2H, s), 6.36 (1H, t), 6.41 (1H, d), 6.82 (1H, m), 7.36 (3H. m), 7.74 (1H, dd), 8.41 (1H, d)	m/z = 436 (M+H)
1-72	4.22 (2H, s), 5.13 (2H, s), 6.14 (1H, m), 6.21 (1H, d), 7.13 (1H. m), 7.26 (7H, m), 7.68 (1H, dd), 8.36 (1H, d)	m/z = 405 (M+H)
1-150	2.08 (3H. S), 2.70 (2H, t), 3.22 (2H, t), 5.15 (2H, s), 6.16 (1H, t), 6.22 (1H, d), 7.17 (1H, m), 7.29 (1H, d), 7.33 (1H, d), 7.70 (1H, dd), 8.38 (1H, d)	m/z = 389 (M+H)
1-67	3.13 (2H. m), 3.73 (2H, t), 5.15 (2H, s), 6.18 (2H, m), 7.17 (1H, m), 7.33 (2H, m). 7.71 (1H, dd), 8.37 (1H, d)	m/z = 359 (M+H)
1-515	0.82 (2H, m), 0.93 (2H, m), 1.40 (1H, m). 5.27 (2H, s), 6.35 (1H. m), 6.42 (1H, d), 7.31 (2H, m), 7.41 (1H, d), 7.77 (1H, dd), 8.38 (1H, d)	m/z = 399 (M+H)
1-56	2.13 (1H, t), 3.85 (2H, d), 5.18 (2H, s), 6.21 (1H, t), 6.25 (1H, d), 7.18 (1H, m), 7.29 (1H, d), 7.33 (1H, d), 7.70 (1H, dd), 8.38 (1H, d)	m/z = 353 (M+H)
1-512	1.02 (3H. t), 2.23 (2H, q), 5.26 (2H, s), 6.34 (1H, m), 6.39 (1H, m), 7.29 (2H, m), 7.40 (1H, d), 7.75 (1H, dd), 8.37 (1H, d)	m/z = 387 (M+H)
1-514	0.97 (6H, s), 2.37 (1H, m), 5.26 (2H, s), 6.35	m/z = 399

.'ViIlHD.D.WIW 1

259

	(1H, m), 6.40 (1 H. d), 7.27 (2H, m), 7.42 (1H, dd), 7.77 (1 H, dd), 8.38 (1H, d)	(M+H)
1-50	0.74 (2H, m), 0.85 (2H, m), 2.51 (1H, m), 5.18 (2H, S), 6.12 (1H, m), 6.30 (1 H, d), 7.15 (1 H, m), 7.27 (1H, m), 7.31 (1H. d), 7.79 (1H, dd), 8.39 (1H, d)	m/z = 355 (M+H)
1-114	3.44 (2H, td), 4.18 (2H, t), 5.14 (2H, s), 6.15 (1H, td), 6.26 (1H, d), 6.86 (2H, d), 6.92 (1H, m), 7.16 (1H, m). 7.28 (4H. m). 7.71 (1H, dd), 8.38 (1H, d)	m/z = 435 (M+H)

[Table 51-3]

1-44	0.83 (3H, t), 1.55 (2H, m), 2.91 (2H, m), 5.14 (2H, S), 6.12 (1H, td), 6.18 (1H, d), 7.13 (1H, m), 7.30 (2H, m), 7.71 (1 H, dd), 8.36 (1H, d)	m/z = 357 (M+H)
1-118	4.41 (2H, S), 5.15 (2H, s), 6.18 (1H, t), 6.24 (1H, d), 7.14 (2H, m), 7.26 (2H, m), 7.54 (1H, d), 7.68 (1H, dd), 7.71 (1H, dd), 8.38 (1H, d), 8.47 (1 H, d)	m/z = 406 (M+H)
1-119	4.22 (2H, s), 5.16 (2H, s), 6.20 (2H, m), 7.15-7.30 (3H, m), 7.34 (1H, dd), 7.61 (1H, d), 7.79 (1H, dd), 8.37 (1H, d), 8.42 (1H, d), 8.46 (1H, d)	m/z = 406 (M+H)

[Table 52-1]

Compound No.	1H-NMR (CDCI3, δ, ppm)	MS or IR (KBr, v, cm’¹)
1-47	0.85 (3H, t), 1.25 (2H, m), 1.53 (2H, m), 2.96 (2H. m), 5.14 (2H. s), 6.10 (1H, m), 6.17 (1H, d), 6.99 ( 1 H, m), 7.27 (2H, m), 7.70 (1H, dd), 8,36 (1H, d)	m/z = 371 (M+H)
1-55	3.65 (2H, m). 5.04 (2H, m), 5.15 (2H, s), 5.90 (1H, m), 6.13 ( 1 H, m), 6.20 (1H, d), 7.13 (1H. m), 7.28 (2H, m), 7.71 (1H, dd), 8.36 (1H, d)	m/z = 355 (M+H)
1-122	4.41 (2H, s), 5.17 (2H, S), 6.17 (2H. m), 6.82 (1H, m). 6.91 (1H. m). 7.16 (2H, m), 7.30 (2H, m), 7.70 (1H, dd), 8.38 (1H, d)	m/z = 411 (M+H)
1-45	1.02 (6H. d), 3.34 (1H, m), 5.13 (2H, s), 6.10 (1H, m), 6.24 (1H, d), 7.11 (1H, m), 7.26 (1H, m), 7.31 (1H, d), 7.68 (1H, dd), 8.35 (1H, d)	m/z = 357 (M+H)

[Table 52-2]

1-124	4.20 (2H, s), 5.17 (2H, s), 6.13-6.29 (4H, m), 7.17 (1H, m), 7.30 (3H, m), 7.71 (1H, dd), 8.38 (1H, d)	m/z = (M+H)	395
1-126	1.49 (1H, m), 1.84 (2H, m), 1.99 (1H, m),	m/z =	399

ΡΠ1Ρ i 1

260

	2.98 (1 H. ddd), 3.14 (1H, ddd), 3.73 (2H, m), 4.09 (1H, m), 5.13 (2H. m), 6.13 (1H, m), 6.20 (1H, d), 7.14 (1H, m), 7.30 (2H, m), 7.70 (1 H, dd), 8.37 (1H, d)	(M+H)
1-64	4.01 (2H, S), 5.24 (2H, s), 6.34 (2H, m), 7.34 (2H, m). 7.41 (1H, dd), 7.66 (1H, dd), 8.36 (1H, d)	m/z = 354 (M+H)
1-146	3.21 (2H, m), 3.34 (2H, s), 3.57 (2H, t), 5.14 (2H, S), 6.15 (1H, m), 6.21 (1H, m), 7.15 (1 H. m), 7.30 (2H, m), 7.72 (1H, dd), 8.37 (1 H, d)	m/z = 373 (M+H)
1-52	1.40-1.77 (8H, m), 3.48 (1H, m), 5.12 (2H, s), 6.09 (1H, m), 6.23 (1H, d), 7.12 (1H, m), 7.24 (1H, m), 7.31 (1 H, d), 7.69 (1H, dd), 8.35 (1H, d)	m/z = 383 (M+H)

[Table 52-3]

1-121	4.18 (2H, s), 5.14 (2H, s), 6.20 (2H, m), 7.19 (3H, m), 7.26 (1 H, m), 7.35 (1H, dd). 7.75 (1 H. dd), 8.36 <1 H. d), 8.51 (2H, m)	m/z = 406 (M+H)
1-53	0.98-1.72 (10H, m), 2.91 (1H, m), 5.11 (2H, s), 6.11 (1H, td), 6.24 (1H, d), 7.11 (1H, m), 7.29 (3H, m), 7.66 (1H, dd), 8.34 (1H, d)	m/z = 397 (M+H)
1-76	2.90 (2H, t), 3.24 (2H, td), 5.07 (2H, s), 6.01 (1H, d), 6.09 (1H. td), 7.02-7.30 (8H, m), 7.61 (1H, dd), 8.34 (1H. d)	m/z = 419 (M+H)
267-2	4.34 (1H, d), 4.62 (1H, d), 6.40 (1 H. d), 7.20 (1H, d), 7.51 (2H, m), 7.59 (1H, dd), 7.63 (2H, m), 7.82 (1H, d), 8.23 (1H, d)	1730, 1689, 1556, 1467, 1440, 1418
253-2	5.31 (2H, S), 7.28 (2H, m), 7.50 (1H, d). 7.72 (3H, m), 7.85 (1 H, m), 8.25 (1H, d), 8.45 (1H, d)	1644, 1557, 1508, 1483
251-2	5.20 (2H, s), 7.26 (2H, m), 7.63 (2H, m), 7.85 (2H, m), 8.02 (1 H, d), 8.23 (2H, m)	3065, 1696, 1463, 1403

[Table 52-4]

13-2	5.76 (2H, s), 6.91 (1H, m), 7.46 (1H, m), 7.60 (1H, m), 7.70 (1H, d), 7.80 (2H, m), 8.12 (1H, d), 8.53 (1H, d)	3060, 2226, 1641, 1556, 1509
1-1	5.49 (2H, s), 6.67 (1H, m), 7.30 (1H, m), 7.60 (1H, m), 7.72 (2H, m), 7.81 (1H, dd), 8.42 (1H, d), 9.06 (1H, s)	-
1-41	5.64 (2H, s), 7.50 (2H, m), 7.70 (1H, d), 7.78 (1H, dd), 8.27 (1H, m), 8.37 (1H, d), 8.78 (1H, d) (methanol-d4)	m/z = 315.16 (M+H)

Γ\·:ΐ 1711 V'i! 'J

261 [Table 53-1]

Compo und No.	1H-NMR (CDCI3, δ, ppm)	MS or IR (KBr, v, cm’
2-2	2.47 (2H, m), 4.17 (2H, t), 5.07 (1H, d), 5.15 (1 H, dd), 5.39 (2H, s), 5.85 (1H, m), 6.43 (1H, td), 7.30 (1H. d), 7.44 (2H, m), 7.75 (1H, dd), 8.08 (1H, d), 8.40 (1 H. d)	m/z = 322 (M+H)
1-647	2.47 (2H, m), 4.17 (2H, t), 5.07 (1H, d), 5.15 (1H, dd), 5.39 (2H, s), 5.85 (1H, m), 6.43 (1H, td), 7.30 (1H, d), 7.44 (2H, m), 7.75 (1H, dd), 8.08 (1H, d), 8.40 (1H, d)	m/z = 318.1013 (M+H)
1-670	3.35(2H, tdd), 5.17 (2H, s), 6.02 (1H, tt), 6.23 (2H, m), 7.22 (1H, m), 7.33 (2H, m), 7.69 (1 H, dd), 8.37 (1H. d)	m/z = 379 (M+H)
157-2	5.51 (2H. s), 6.63 (1H, dd), 7.42 (1H, d), 7.77 (1H, d), 7.84 (1H, dd), 8.26 (1H, d), 8.45 (1H, d)	m/z = 332 (M+H)
1-10	1.61 (1H, m), 2.29 (2H, m), 4.73 (2H, s), 7.26 (1H, m), 7.31 (1 H, m), 7.69 (1H, m), 7.79 (1H, m), 8.23 (1H. d), 8.40 (1H, d), 8.57 (1H, d)	m/z = 324 (M+H)
580-2	5.47 (2H, s), 6.89 (1H, m), 7.47 (2H, m), 7.82 (2H, m), 8.41 (1H, s), 8.56 (1H, d)	m/z = 332 (M+H)
1-671	0.87 (3H, t), 1.28 (10H, m), 1.55 (2H, m), 2.96 (2H, t), 5.14 (2H, s), 6.13 (1 H. t), 6.18 (1H, d), 7.13 (1H, m), 7.30 (2H, m), 7.71 (1H, dd), 8.37 (1H, d)	m/z = 427 (M+H)
1-658	0.87 (3H, t), 1.25 (26H, m), 1.55 (2H, m), 2.96 (2H, t), 5.14 (2H, s), 6.11 (1H, t), 6.17 (1H, d), 7.13 (1H, m), 7.30 (2H, m), 7.70 (1H, dd), 8.36 (1H, d)	m/z = 539 (M+H)
1-659	0.87 (3H, t), 1.26 (18H, m), 1.53 (2H, m), 2.95 (2H, t), 5.14 (2H, s), 6.12 (1H, t), 6.18 (1H, d), 7.13 (1H, m), 7.31 (2H, m), 7.71 (1H, dd), 8.36 (1 H. d)	m/z = 483 (M+H)

a*

262 '

[Table 53-2]

1-660	0.74 (3H, t), 0.97 (3H, d), 1.42 (2H, m), 3.08 (1H, m), 5.12 (2H, dd), 6.09 (1 H. t), 6.23 (1H, d), 7.11 (1H, m), 7.24 (1H, m), 7.30 (1H, d), 7.67 (1H, dd), 8.35 (1 H. d)	m/z = 371 (M+H)
1-681	0.77, 0.90 (6H, t*2), 1.40 (4H, m), 2.97 (1H, m), 5.11 (2H, s), 6.10 (1H, t), 6.25 (1H, d), 7.11 (1H, m), 7.24 (1H, d), 7.32 (1H, d), 7.66 (1H, dd), 8.34 (1 H. d)	m/z - 385 (M+H)
1-686	0.81, 0.91 (6H, t*2), 1.02-1.45 (8H, m), 3.19 (1H, m), 5.12 (2H, s), 6.10 (1H, t), 6.25 (1H, d), 7.11 (1H, m), 7.22 (1 H. d), 7.30 (1H, d), 7.64 (1H, dd), 8.33 (1H, d)	m/z = 413 (M+H)
1-661	0.81 (3H, t), 0.97 (3H, d), 0.90-1.50 (4H, m), 3.19 (1H, m), 5.07 (1H, d), 5.15 (1H, d), 6.09 (1H, t), 6.24 (1 H. d), 7.11 (1H, m), 7.27 (2H, m), 7.66 (1H. dd), 8.34 (1H, d)	m/z = 385 (M+H)
1-662	0.75 (3H, d), 0.80 (3H, d), 0.94 (3H, d), 1.61 (1H, m), 2.86 (1H. m), 5.11 (2H, s), 6.09 (1H, t), 6.23 (1H, d), 7.11 (1H, t), 7.25 (1H, d), 7.30 (1H, d), 7.66 (1H, dd), 8.34 (1H, d)	m/z = 385 (M+H)

[Table 53-3]

1-663

1.35 (3H, d), 4.33 (1H, q), 5.05 (1H, d), 5.11 (1H, d), 6.00 (1H, d), 6.08 (1H, t), 6.96 (1H. m), 7.15-7.26 (7H, m), 7.63 (1H, dd), 8.33 (1H. d)

m/z = 419 (M+H)

263 l’V.I 1,1, ]

1-664	1.55-1.75 (3H, m), 1.95 (1H, m). 2.70-2.88 (2H, m). 4.36 (1H. t), 5.05 (1H. d), 5.20 (1 H. d), 6.13 (1H, t), 6.38 (1H. d), 6.96 (1H, m), 7.02-7.20 (SH. m). 7.28 (1H. d), 7.62 (1H, dd), 8.3 (1H, d)	m/z = 445 (M+H)
1-665	1.57 (3H. d), 4.78 (1H, d). 4.91 (1 H. d), 5.18 (1H, q), 5.80 (1H, d), 5.93 (1H, t), 6.72 (1H, m), 7.05 (1 H. d), 7.14 (1 H. d), 7.38 (3H, m), 7.54 (1H, dd), 7.62 (1H. d). 7.66 (1H, d), 7.80 (1H, d), 7.84 (1H, d), 8.28 (1H, d)	m/z = 469 (M+H)
1-666	0.74 (3H, t), 1.75 (2H, m), 4.03 (1H, t), 5.06 (2H, dd), 5.85 (1H. d), 6,05 (1 H. m), 6.86 (1H, m), 7.10-7.28 (7H, m), 7.63 (1H, dd), 8.33 (1H, d)	m/z = 433 (M+H)

[Table 53-4]

1-667	1.34 (3H, d), 4.45 (1H, q), 5.11 (1H, d), 5.16 (1H, d), 6.07 (1H, m), 6.14 (1 H. td), 6.26 (2H, m), 7.11 (1H. m), 7.28 (3H, m), 7.67 (1H, dd), 8.36 (1H. d)	m/z = 409 (M+H)
1-676	5.06 (2H, s), 5.37 (1H. s), 5.38 (1H, d), 6.07 (1 H. t), 6.85 (1H, t), 7.10-7.28 (12H, m), 7.61 (1H, d), 8.33 (1H, s)	m/z = 481 (M+H)

264 .d · ' I sjir I [Table 54-1]

1-668	0.79 (9H, s), 0.85 (3H, d), 2.89 (1H, q), 5.11 (2H, S), 6.08 (1H, t), 6.23 (1 H. d), 7.10 (1H, t), 7.23 (1H, d), 7.30 (1H, d), 7.65 (1H, d), 8.34 (1H, s)	m/z » 399 (M+H)
47-2	5.68 (2H, d), 6.57 (1H, m), 7.34 (1H, d), 7.80 (1H, m), 7.97 (1H, dd), 8.39 (1H. d), 8.57 (1H, s)	m/z = 334 (M+H)
91-2	5.92 (2H, s), 6.95 (1H, d), 7.30 (1H, d), 7.69 (1H, m), 7.86 (1H, dd), 8..49 (1H. dd), 8.53 (1H. d)	m/z - 350 (M+H)
478-2	2.59 (3H, s), 5.77 (2H, s). 6.75 (1 H, d), 7.31 (1H, d), 7.63 (1H, dd), 7.72 (1 H, m), 8.33 (1H, d), 8.45 (1H, d)	m/z = 330 (M+H)
479-2	2.73 (3H, s), 5.71 (2H, s), 6.73 (1H, d), 7.63 (1 H, s), 7.69 (1H, t), 8.44 (1H, d)	m/z = 336 (M+H)

[Table 54-2]

1-51	1.60 (2H, m), 1.73 (1H, m), 2.03 (4H, m), 3.75 (1H, m), 5,12 (2H, s), 6.12 (1H, t), 6.16 (1H, d), 7.10 (1H, m), 7.25 (1H, d), 7,32 (1H, d), 7.71 (1H, dd), 8.37 (1H, d)	m/z = 369 (M+H)
566-2	4.09 (3H, s), 5.71 (2H, s), 6.25 (1H, d), 7.29 (1H, d), 7.74 (1 H. t), 7.97 (1H, dd), 8.17 (1H, d), 8.50 (1H, d)	m/z = 346 (M+H)

265 •\·; i ’n \ *·’’ i > ),<

488-2	1.77 (1H, m), 2.11 (1H, m), 2.62 (3H, s), 2.98 (1H, m), 3.53 (1 H, dd), 3.67 (1 H. dd), 3.78 (1H, m), 3.98 (1H, m), 4.22 (1 H, m), 4.65 (1H. m), 6.73 (1H. d), 7.66 (1H. t). 8.32 (1H. d)	m/z = 289 (M+H)
511-2	5.58 (2H. s), 7.38 (1H, d). 7.86 (1H, dd). 8.40 (1 H. dd). 8.47 (1H. d). 8.55 (1H. d), 8.93 (1 H, d)	m/z - 361 (M+H)

[Table 54-3]

1-669	1.42 (3H, d), 4.65 ( 1 H, q), 5.12 (2H, s), 6.13 (2H, m), 6.75 (1H, d), 6.88 (1H, dd), 7.07 (1H. m), 7.11 (1H. d), 7.26 (2H, m), 7.65 (1H. dd), 8.35 (1H, d)	m/z = 425 (M+H)
179-2	5.30 (2H, s), 6.43 (1H, dd), 6.66 (1H, dd), 7.40 (1H, d), 7.60 (2H, m). 8.20 (1H. d)	m/z = 332 (M+H)
555-2	3.87 (3H, s). 5.60 (2H, s), 7.51 (1H, d), 7.88 (1H. dd), 7.93 (1H, dd), 8.34 (1H. d), 8.49 (1H. d), 8.56 (1H, d) (DMSO-d6)	m/z = 346 (M+H)
577-2	5.65 (2H, s). 6.87 (1H. td), 7.30 (1H, d), 7.81 (1H, m), 8.08 (1H, dd), 8.13 (1H. d), 8.54 (1H, d)	m/z = 349 (M+H)
544-2	3.93 (3H, S), 5.45 (2H. s). 6.49 (1H, dd), 7.31 (1H, d), 7.66 (1H. d), 7.83 (1H, dd), 8.13 (1H, d), 8.42 (1H, d)	m/z = 346 (M+H)

266 l> < I .11'1 > u

168-2

5.62 (2H. s), 7.43 (1H, d), 7.64 (1 H, dd). 7.88 (1H. dd), 7.94 (1H, d), 8.26 (1H, d), 8.49 (1H, d)

m/z = 332 (M+H)

[Table 54-4]

1-644	4.18 (2H, s), 4.68 (2H. s). 5.36 (2H. s), 6.55 (1H, m), 7.16 (1H, d). 7.29 (1H. d), 7.35 (2H, m). 7.40 (2H. m). 7.52 (2H, m), 7.75 (1H, dd), 8.28 (1H, d). 8.40 (1H, d)	m/z = 368 (M+H)
578-644	4.19 (2H, s), 4.69 (2H, s). 5.42 (2H, s). 6.52 (1H, m), 7.20 (1H, m), 7.30 (1H, m). 7.32 (2H. m). 7.40 (2H, m). 7.55 (2H, m), 7.72 (1H. dd), 8.30 (1H. dd), 8.52 (1H, dd), 8.62 (1H, d)	m/z = 334 (M+H)
1-703	5.20 (1H. d). 5.45 (1 H.d). 6.55 (1H, m) 7.34 (1H, m), 7.50 (1H, m), 7.60 (1H, m), 7.79 (1H. dd), 8.39 (1H, d)	1715, 1636, 1552, 1505, 1457, 1174, 1144
1-707	5.43 (2H. s). 6.93 (1H, m). 7.36 (1H, d), 7.77-7.85 (3H. m), 7.95 (1H, dd). 8.39 (1H, d)	(EI-HRMS) m/z = 351.0084 (M+)
1-706	1.20 (6H, m). 2.67 (4H, m), 5.22 (2H, s), 6.52 (1H. m),. 7.31 (1H, m), 7.51 (1H, m), 7.60 (1H, dd), 7.73 (1H, m), 7.84 (1H, d), 8.41 (1H, d)	m/z = 298 (M+H)

267

1' !

[Table 54-5]

1-692	1.11(3H, t), 1.20 (3H, t), 3.76 (2H, m), 3.92 (2H, m), 6.58 (1H, m), 7.26 (1H, d)., 7.53 (2H, m), 7.74 (1H, dd), 8.12 ( 1 H. d). 8.40 (1H. d) (DMSO-d6)	m/z = 356 (M+H)
1-700	1.20 (6H, m), 2.67 (4H, m), 5.22 (2H, s), 6.52 (1H, m),. 7.31 (1H, m), 7.51 (1H, m), 7.60 (1H, dd), 7.73 (1 H, m), 7.84 (1H, d), 8.41 (1H, d)	m/z = 404 (M+H)
1-701	0.95 (6H, m), 1.56 (4H, m). 2.62 (4H, m), 5.18 (2H, s), 6.52 (1H, m), 7.34 (1H, m), 7.49 (1H, m), 7.59 (1H, m), 7.77 (1H, dd), 7.84 (1H, d), 8.42 (1H, d)	m/z = 432 (M+H)
1-702	1.13-1.46 (m, 12H), 3.20 (m, 2H), 5.27 (s, 2H), 6.51 (m, 1H), 7.31 (m, 1H), 7.52 (m, 1H), 7.63 (m, 1H), 7.78 (m, 2H), 8.43 (d, 1H)	m/z = 432 (M+H)
1-646	1.31 (6H, d), 4.95 (1H, sep), 5.40 (2H, s), 6.40 (1H, m), 7.28 (1H, d), 7.40 (2H, m), 7.73 (1H, dd) 8.05 (1H, m), 8.40 (1H, d)	1646, 1620, 1548, 1504, 1453,

[Table 54-6]

1-645	5.18 (2H, s), 5.37 (2H, s), 6.43 (1H, m), 7.25-7.36 (4H, m), 7.41-7.46 (4H, m), 7.72 (1H, dd), 8.12 (1H, m), 8.38 (1H, d)	1655, 1518, 1455, 1399, 1235
1-643	5.52 (2H, s), 6.78 (1H, m), 7.31 (1H, d), 7.68-7.75 (3H, m), 8.39 (1H, m), 8.56 (1H, s)	1633, 1601, 1541, 1502,

268

I » ' ’

		1482, 1453, 1384
2-643	5.51 (2H, s), 6.80 (1H, m), 7.60 (1H, s), 7.75 (2H, m), 8.57 (1H, m)	1632, 1597, 1541, 1506, 1483, 1455, 1388

Further, the synthetic methods In the Table are described as follows.

A: the same method as In Synthetic Example 1

B: the same method as in Synthetic Example 2

C: the same method as in Synthetic Example 3

D: the same method as in Synthetic Example 4

E: the same method as in Synthetic Example 5

F: the same method as in Synthetic Example 6

G: the same method as in Synthetic Exampies 7 and 8

H: the same method as In Synthetic Example 9 Préparation Exampie [Préparation Example]

Préparation Example 1 [Wettable powder]

Compound P212	10% by weight
Imidacloprid	20% by weight
Clay	50% by weight
White carbon	2% by weight
Diatomaceous earth	13% by weight
Calcium ligninsulfonate	4% by weight
Sodium lauryl sulfate	1% by weight

. \ -.ii >7in > \ i

269

The Ingrédients were homogeneousiy mixed and ground to obtain wettable powder.

Préparation Example 2 [Water dispersible granule]

Compound P212	10% by weight
Imidacloprid	20% by weight
Clay	60% by weight
Dextrin	5% by weight
Alkyl maleate copolymer	4% by weight
Sodium lauryl sulfate	1% by weight

The ingrédients were homogeneousiy ground and mixed, water was added thereto to knead the Ingrédients thoroughiy and then the mixture was granuiated and dried to obtain water dispersible granules.

Préparation Example 3 [Flowables]

Compound 1-20	5% by weight
Imidacloprid	20% by weight
POE poiystyrylphenyl ether sulfate	5% by weight
Propylene glycol	6% by weight
Bentonite	1% by weight

1% xanthan-gum aqueous solution 3% by weight

PRONALEX-300 (TOHO Chemical Industry Co., Ltd.)

0.05% by weight

ADDAC827 (Kl Chemical Industry Co., Ltd.) 0.02% by weight

Water added to 100% by weight

Ail the ingrédients except for the 1% xanthan-gum aqueous solution and a suitable amount of water were premixed together from the blending, and the mixture was then ground by a wet grinder. Thereafter, the 1% xanthan-gum aqueous solution

270 and the remaining water were added thereto to obtain 100% by weight of flowables.

Préparation Exarnple 4 [Ernulsifîable concentrate]

Compound P212 2% by weight

Imidacloprid 13% by weight

N,N-dimethylformamîde 20% by weight

Solvesso 150 (Exxon Mobil Corporation) 55% by weight

Polyoxyethylene alkyl aryl ether 10% by weight

The Ingrédients were homogeneously mixed and dissolved to obtain an ernulsifîable concentrate.

Préparation Example 5 [Dust]

Compound P212

0,5% by weight

Imidacloprid

1.5% by weight

Clay

60% by weight

Talc

37% by weight

Calcium stéarate

1% by weight

The Ingrédients were homogeneously mixed to obtain dust.

Préparation Example 6 [DL Dust]

Compound P212

1% by weight

Tebufloquin

1% by weight

Ethofenprox

1% by weight

DLelay

94.5% by weight

White carbon

2% by weight

Light liquid paraffin

0.5% by weight

The ingrédients were homogeneously mixed to obtain dust.

Préparation Example 7 [Microgranule fine]

Compound P212

1% by weight

271

Imidacloprid

1% by weight

Carrier

94% by weight

White carbon

2% by weight

Hiso! SAS-296

2% by weight

The ingrédients were homogeneously mixed to obtain dust.

Préparation Example 8 [Granules]

Compound 1-20

2% by weight

Chlorantraniliprole

1% by weight

Bentonite

39% by weight

Taie

10% by weight

Ciay

46% by weight

Calcium ligninsulfonate

2% by weight

The ingrédients were homogeneously ground and mixed, water was added thereto to knead the ingrédients thoroughly, and then the mixture was granulated and dried to obtain granules.

Préparation Example 9 [Microcapsules]

Compound 1-20

2% by weight

Imidacloprid

3% by weight

Urethane resin

25% by weight

Emulsifier/Dispersant

5% by weight

Antiseptie

0.2% by weight

Water

64.8% by weight

Microcapsules were obtained by forming a urethane resin coating on the surface of particles of the compound represented by Formula (I) and imidacloprid particles using the ingrédients by interfacial polymerization.

Préparation Exemple 10 [Granules]

272

Compound P212	2% by weight
Probenazole	24% by weight
Sodium lauryl sulfate	1% by weight
Bentonlte	2% by weight
Calcium stéarate	1% by weight
PVA	2% by weight
Clay	68% by weight

Préparation Example 11 [Granules]

Compound P212	2% by weight
Chlorantraniliprole	1% by weight
Probenazole	24% by weight
Bentonite	40% by weight
Talc	10% by weight
Clay	21% by weight
Calcium ligninsulfonate	2% by weight

Préparation Example 12 [Liquid drops]

Compound 1-20	10% by weight
Fipronil	1% by weight
Benzyl alcohol	73.9% by weight
Propylene carbonate	15% by weight
“ ' ' ' 1 ’i) 1	273

ΒΗΤ

0.1% by weight

The Ingrédients were homogeneously stirred and dîssolved to obtain liquid drops.

Préparation Example 13 [Liquid drops]

Compound P212

48% by weight

Fipronil

2% by weight

Ethanol

50% by weight

The ingrédients were homogeneously mixed to obtain liquid drops.

Préparation Example 14 [Emulsifiable concentrate]

Compound 1-20

5% by weight

Etoxazole

5% by weight

Xylene

35% by weight

Dimethyl sulfoxlde

35% by weight

The Ingrédients were dîssolved, and 14% by weight of polyoxyethylene styryl phenyl ether and 6% calcium dodecylbenzenesulfonate were added thereto, and the mixture was thoroughly stirred and mixed to obtain a 10% emulsifiable concentrate.

Préparation Exampie 15 [Liquid drops]

Compound P212

10% by weight

Etoxazole

5% by weight

Glycol (glycol mono alkyl ether) 85% by weight

BHT or BHA appropriate amount

An appropriate amount of sorbitan monooieate or sorbîtan monolaurate, caprylic acid monoglyceride or isostearic acid monoglyceride, or propylene giycol monocaprylate was added to the ingrédients, and alcoho! or propylene carbonate, Nmethyt-2-pyrrolidone or water was added thereto to obtain liquid drops as 100% by weight.

Reference Test Exampie

274 .> 11 ' 'i j·,-·- 1 <Foliar treatment test of single agent*

Reference Test Example 1 Pest control test of Plutella xvlostella

A leaf disk having a diameter of 5.0 cm was eut out from a cabbage in pot culture, and a drug solution of the compound of Formula (I) at a predetermined concentration, which had been prepared so as to be a 50% acetone water (0.05% Tween20 available), was sprayed to the leaf disk. After an air drying process, second Instar larvae were released thereto. Thereafter, the larvae were left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25°C. Three days after the release, the iarvae were observed for survival or death, and the mortality of larvae was calculated by the following équation. Test In duplicate.

Mortality (%) = {number of dead larvae/(number of survived larvae + number of dead larvae)) x 100

As a resuit, compounds P212 and 1-20 exhibited Insecticidal activity having a mortality of 80% or higher by a foliar treatment at 100 ppm.

Reference Test Example 2 Pest control test of Spodoptera lîtura

A leaf disk having a diameter of 5.0 cm was eut out from a cabbage In pot culture, and a drug solution of the compound of Formula (I) at a predetermined concentration, which had been prepared so as to be a 50% acetone water (0.05% Tween20 available), was sprayed to the leaf disk. After an air drying process, third instar larvae were released thereto. Thereafter, the larvae were left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25°C. Three days after the release, the larvae were observed for survival or death, and the mortality of larvae was calculated by the following équation. Test In duplicate.

Mortality (%) - {number of dead larvae/(number of survived larvae + number of dead larvae)} x 100

As a resuit, compounds P212 and 1-20 exhibited insecticidal activity having a

275 mortality of 80% or higher by a foiiar treatment at 500 ppm.

Reference Test Example 3 Pest control test of Aphls oossypil

A leaf disk having a diameter of 2.0 cm was eut out from a cucumber in pot culture, and a drug solution of the compound of Formula (I) at a predetermined concentration, which had been prepared so as to be a 50% acetone water (0.05% Tween20 available), was sprayed to the leaf disk. After an air drying process, first instar larvae were released thereto. Thereafter, the larvae were left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25°C. Three days after the reiease, the larvae were observed for survival or death, and the mortality of larvae was calculated by the following équation. Test ln duplicate.

Mortality (%) » (number of dead larvae/(number of survived larvae + number of dead larvae)) x 100

As a resuit, compounds P212 and 1-20 exhlbited Insecticidal activity having a mortality of 80% or higher by a foiiar treatment at 100 ppm.

Reference Test Example 4 Pest control test of Laodelphax striatella

A drug solution of the compound of Formula (I) at a predetermined concentration, which had been prepared so as to be a 50% acetone water (0.05% Tween20 available), was foiiar sprayed to a rice seedling ln pot culture. After an air drying process, second Instar larvae were released thereto. Thereafter, the larvae were left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25°C. Three days after the reiease, the larvae were observed for survival or death, and the mortality of larvae was calculated by the following équation. Test ln duplicate.

Mortality (%) = (number of dead larvae/(number of survived larvae + number of dead larvae)) χ 100

As a resuit, compounds P212 and 1-20 exhibited Insecticidal activity having a mortality of 80% or higher by a foiiar treatment at 100 ppm.

276

P v.in . > _k , .m

Reference Test Exemple 5 Pest control test of Nilaparvata luqens

A drug solution of the compound of Formula (I) at a predetermined concentration, which had been prepared so as to be a 50% acetone water (0.05% Tween20 available), was foliar sprayed to a rice seedling in pot culture. After an air drying process, second instar larvae were released thereto. Thereafter, the larvae were left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25°C. Six days after the release, the larvae were observed for survival or death, and the mortality of larvae was calculated by the following équation. Test in duplicate.

Mortality (%) - {number of dead larvae/(numberof survived larvae + number of dead larvae)} χ 100

As a resuit, compounds P212 and 1-20 exhibited insecticidai activity having a mortality of 80% or higher by a foliar treatment at 100 ppm.

Reference Test Example 6 Pest control test of Soqatella furcifera

A drug solution of the compound of Formula (I) at a predetermined concentration, which had been prepared so as to be a 50% acetone water (0.05% Tween20 available), was foliar sprayed to a rice seedling in pot culture. After an air drying process, second instar larvae were released thereto. Thereafter, the larvae were left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25°C. Four days after the release, the larvae were observed for survival or death, and the mortality of larvae was calculated by the foliowing équation. Test in duplicate.

Mortality (%) - {number of dead larvae/fnumber of survived larvae + number of dead larvae)} χ 100

Reference Test Example 7 Pest control test of Nephotettix cincticeps

A drug solution of the compound of Formula (I) at a predetermined concentration,

277 which had been prepared so as to be a 50% acetone water (0.05% Tween20 available), was foliar sprayed to a rice seedling in pot culture. After an air drying process, second instar larvae were released thereto. Thereafter, the larvae were left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25°C. Four days after the release, the larvae were observed for survival or death, and the mortality of larvae was calculated by the following équation. Test In duplicate.

As a resuit, compound P212 exhibited Insecticidal activity having a mortality of 80% or higher by a foliar treatment at 100 ppm.

Reference Test Example 8 Pest control test of trialeurodes vaporariorum

Adult greenhouse whlteflies were released to a cucumber in pot culture and ailowed to lay eggs ovemight. One day after the onset of egg laying, the aduits were removed and the eggs were left to stand ln a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25°C. Three days after the completion of egg laying, a leaf disk having a diameter of 2.0 cm was eut out from the cucumber, It was conflrmed that the eggs had been laid, and then a drug solution of the compound of Formula (I) at a predetermined concentration, which had been prepared so as to be a 50% acetone water (0.05% Tween20 available), was sprayed to the leaf disk. After the spraying, the leaf disk was left to stand In a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25°C. Fourteen days after the spraying, larvae were observed for survival or death, and the mortality of larvae was calculated by the following équation. Test in duplicate.

Mortality of larvae (%) = {(number of eggs laid - number of survived larvae)/number of eggs laid)} x 100

As a resuit, compound P212 exhibited high insecticidal activity having a mortality

278 of 80% or higher by a foliar treatment at 100 ppm.

Reference Test Exampie 9 Pest control test of Franklinieîla occidentalis

A leaf disk having a diameter of 2.8 cm was eut out from a kidney bean in pot culture, and a drug solution of the compound of Formula (I) at a predetermined concentration, which had been prepared so as to be a 50% acetone water (0.05% Tween20 available), was sprayed to the leaf disk. After an air drying process, first instar larvae were released to the leaf disk. Thereafter, the larvae were left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25°C. Three days after the release, the larvae were observed for survival or death, and the mortality of larvae was calculated by the following équation. Test in duplicate.

Mortality of larvae (%) = (number of dead iarvae/(number of survived iarvae + number of dead larvae)) χ 100

As a resuit, compounds P212 and 1-20 exhibited high insecticidal activity having a mortality of 80% or higher by a foliage treatment at 500 ppm.

Reference Test Example 10 Pest controi test of Triqonotvlus caelestialium

Wheat seedling leaves and stems four days after the dissémination of seedlings were dipped for 30 seconds In a drug solution of the compound of Formula (I) at a predetermined concentration, which had been prepared so as to be a 50% acetone water (0.05% Tween20 available). After an air drying process, the wheat seedling leaves and stems were placed into a glass tube, and two second instar larvae of Trigonotylus coelestialium were released to the same glass tube. After the larvae were released, the tube was lldded to leave the iarvae to stand in a thermostatic chamber at 25°C. In order to supply water to the wheat during the test, water was given to the wheat from the bottom of the glass tube. Three days after the treatment, the larvae were observed for survival or death, and the death rate of larvae was calculated by the following équation. Test in triplicate.

279 . m ' ' ¹ l

Mortality of larvae (%) = {number of dead larvae/(number of survived larvae + number of dead larvae)} x 100

As a resuit, compounds P212 and 1-20 exhîbited insecticidal activity having a mortality of 80% or higher by a dipping treatment of the drug solution at 50 ppm.

Reference Test Exemple 11 Pest control test of Plautia crossota stali

A drug solution of the compound of Formula (I) at a predetermined concentration, which had been prepared so as to be a 50% acetone water (0.05% Tween20 available), was sprayed to a young fruit of apple collected outdoors. After an air drying process, the young fruit was placed into a plastic cup, and two adults of Piautia crossota stali were released thereto. Six days after the release, the adults were observed for survival or death, the Mortality of adults was calculated by the foliowing équation.

Mortality of adults (%) = {number of dead adults/(number of survived adults + number of dead adults)} x 100

As a resuit, compound P212 exhibited insecticidal activity having a mortality of 60% or higher by a foliar treatment at 50 ppm.

Reference Test Example 12 Pest control test of Ouléma oryzae pL(/head) of a drug solution of the compound of Formula (I) prepared at a predetermined concentration with acetone was topically applied and treated to the back of adults collected outdoors by a micro syringe. After the drug treatment, the adults were transferred to rice seedlings and left to stand in a thermostatic chamber at 25°C so as to obtain 5 heads per stem. Forty eight hours after the treatment, the adults were observed for survival or death, and the mortality of adults was calculated by the foliowing équation. Test in duplicate.

Mortality of adults (%) = {number of dead adults/(number of survived adults + number of dead adults)} χ 100

280

-’x'iir ·« i c'h ' of 80% or higher In a throughput of 0.5 pg/head.

Reference Test Example 13 Pest control test of Musca domestica

The backs of female adults raised Indoors were treated with 1 pL(/head) of a drug solution of the compound of Formula (i) prepared at a predetermined concentration with acetone. After the drug treatment, the adults were transferred to a plastic cup and left to stand In a thermostatic chamber at 25°C so as to obtain 5 heads per cup. Twenty four hours after the treatment, the agony situation of the adults was observed, and the rate of agonized adults was calculated by the following équation. Test In duplicate.

Mortality of adults (%) = {number of dead adults/(number of survived adults + dead adults)) χ 100

As a resuit, compounds P212 and 1-20 exhibited high Insecticidal activity having a mortality of 80% or higher In a throughput of 2 pg/head.

Reference Test Example 14 Pest control test of Laodelphax striatella

A rice seedling In pot culture was subjected to soil drench treatment with a drug solution of the compound of Formula (I) at a predetermined concentration, which had been prepared so as to be a 10% acetone water. Three days after the treatment, ten second instar larvae of Laodelphax striatella were each released thereto. Thereafter, the larvae were left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25°C. Three days after the release, the larvae were observed for survival or death, and the mortality of larvae was calculated by the following équation. Test in duplicata.

Mortality of larvae (%) = {number of dead larvae/(number of survived larvae + number of dead larvae)) χ 100

As a resuit, compounds P212 and 1-20 exhibited high insecticidal activity having

281 > ίΓ'··.; · ’ ;

a mortality of 80% or higher ln a throughput of 0.05 mg/seediing.

Reference Test Example 15 Pest control test of Soaatella furcifera

A rice seedling in pot culture was subjected to soil drench treatment with a drug solution of the compound of Formula (I) at a predetermined concentration, which had been prepared so as to be a 10% acetone water. Three days after the treatment, ten second Instar larvae of Sogatella furcifera were each released thereto. Thereafter, the larvae were left to stand ln a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25°C. Three days after the release, the larvae were observed for survival or death, and the mortality of larvae was calculated by the following équation. Test ln duplicate.

Mortality of larvae (%) = {number of dead larvae/(number of survived larvae + number of dead larvae)) x 100

As a resuit, compounds P212 and 1-20 exhibited high Insecticldal activity having a mortality of 80% or higher in a throughput of 0.05 mg/seedling.

Reference Test Example 16 Pest control test of Nilaparvata luoens

A rice seedling In pot culture was subjected to soil drench treatment with a drug solution of the compound of Formula (I), which had been prepared so as to be a 10% acetone water. Three days after the treatment, ten second Instar larvae of Nilaparvata lugens were each released thereto. Thereafter, the larvae were left to stand ln a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25°C. Three days after the release, the larvae were observed for survival or death, and the mortality of larvae was calculated by the following équation. Test in duplicate.

As a resuit, compounds P212 and 1-20 exhibited high Insecticidal activity having a death rate of 80% or higher ln a throughput of 0.05 mg/seedling.

282 ' . i !'T o

Reference Test Example 17 Pest control test of Llssorhoptrus orvzophilus

A rice seedling in pot culture was subjected to soi! drench treatment with a drug solution of the compound of Formula (I), which had been prepared so as to be a 10% acetone water. Two days after the treatment, five adults of Llssorhoptrus oryzophilus were each released thereto. Thereafter, the larvae were left to stand In a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25°C. Three days after the reiease, the larvae were observed for survival or death, and the mortality of larvae was calculated by the following équation. Test In dupllcate.

As a resuit, compound P212 exhibited high insectlcldal activity having a mortality of 80% or higher In a throughput of 0.1 mg/seedling.

Reference Test Example 18 Pest control test of Laodelphax striatella

Wheat seedling roots forty eight hours after the dissémination of seeds were treated with a drug solution of the compound of the présent invention at a predetermined concentration, which had been prepared so as to be a 10% acetone water. The drug was absorbed from the roots for 72 hours, and then ten second Instar larvae of Laodelphax striatella were each released thereto. Thereafter, the larvae were left to stand In a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25°C. Four days after the reiease, the larvae were observed for survival or death, and the mortality of larvae was calculated by the following équation. The test was performed In dupllcate,

As a resuit, compounds P212 and 1-204 exhibited insecticldal activity having a mortality of 80% or higher in a throughput of 20 pg/seedllng.

Ι·'Ί ''Ί. 1.

283

The results of Référencé Test Examples 1,3 and 18 are shown in the following Table.

[Table 55-1]

Reference Example Compound No.	Ar	Y	R	Piuteila xylostella (Referenc e Test Example D	Aphls gossypli (Referenc e Test Example 3)	Laodelph ax striatella (Referenc e Test Example 18)
P-212	6-chloro-3pyrldyl	H	COCF3	100	100	100
P-213	2-chloro-5thlazolyl	H	COCF3	100	100	100
P-215	6-chloro-3pyridyl	5-CI	COCF3	100	80	75
P-216	6-chloro-3pyridyl	5-F	COCF3	100	95	100
P-218	2-chloro-5thiazolyl	5-CI	COCF3	100	60
P-219	2-chloro-5thlazolyl	5-F	COCF3	80	85
P-222	6-chloro-3pyridyl	4-Me	COCF3		100	100
P-223	6-chloro-3pyridyl	5-Me	COCF3		75	75
P-225	4-chlorophenyl	H	COCF3		90
P-226	3-pyridyl	H	COCF3	60	100
P-227	6-chloro-5fluoro-3pyrldyl	H	COCF3	100	100	100
P-228	6trifluoromethy I-3- pyridyl	H	COCF3	30	95	100
P-229	6-fluoro-3pyridyl	H	COCF3	100	100	100
P-230	5,6-dlchloro3-pyridyl	H	COCF3	100	100

[Table 55-2]

P-231	6-bromo-3pyrldyl	H	COCF3	100	100	100
P-232	6-chloro-3pyridyl	4-F	COCF3		80
P-233	6-chioro-3pyrldyl	3-F	COCF3		100	75

284

/.prn. H

P-234	6-chloro-3pyridyl	H	C0CHCI2	100	100	100
P-235	6-chloro-3pyrldyl	H	C0CCI3	100	95	75
P-236	6-chloro-3pyrldyl	H	C0CH2CI		100
P-238	6-chloro-3pyridyl	H	C0CHF2	100	100	100
P-239	6-chloro-3pyridyl	H	C0CF2CI	100	100	100
P-240	6-chloro-3pyridyl	H	COCHCIBr		100	100
P-241	6-chloro-3pyridyl	H	C0CHBr2		100	100
P-242	6-chloro-3pyridyl	H	COCF2CF 3	100	100	100
P-243	2-chloro-5pyrlmidlnyl	H	COCF3	100	100	100
P-244	6-chloro-3pyridyl	H	C0CH2Br		100	100
1-20	6-chloro-3pyridyl	H	CSCF3	100	100	100
1-21	6-chloro-3pyrldyi	H	CSCHF2	80	100	100
1-22	6-chloro-3pyrldyl	H	CSCF2CI	100		100
1-23	6-chloro-3pyrldyl	H	CSCF2CF 3	100		100
1-42	6-chloro-3pyrldyl	H	C(=NOMe) CF3	100	100	100
1-150	6-chloro-3pyridyi	H	C(=NCH2C H2 SMe)CF3	100	100	80

[Table 55-3]

3-3	6-fluoro-3pyridyl	H	COCHF2	50	100	80
3-4	6-fluoro-3pyrldyl	H	COCF2CI	100	100	100
3-5	6-fluoro-3pyrldyl	H	COCF2CF 3	100	55	80
3-20	6-fluoro-3pyrldyi	H	CSCF3	55	100	80
4-3	6-Bromo-3pyridyl	H	COCHF2	100		100
4-4	6-Bromo-3pyrldyl	H	COCF2CI	100		100
4-5	6-Bromo-3pyridyl	H	COCF2CF 3	100	100	100
4-20	6-Bromo-3-	H	CSCF3	100	100	100

285

- Ο.'Λ’ί IUU. *

	pyridyl
5-3	6ChioroSfiuoro3pyridy!	H	COCHF2	100		100
5-4	6Chloro5fiuoro3pyrldyl	H	COCF2CI	100		100
5-20	6Chloro5fiuoro3pyridyl	H	CSCF3	100		100
6-3	2-CI-5pyrimidlnyl	H	COCHF2	80		100
6-4	2-CI-5pyrimidinyl	H	COCF3CI	90	100	100
102-2	6-chloro-3pyridyl	3-CN	COCF3	10	100	100

Reference Test Example 19 Pest control test of Nilaparvata lugens

A rice seedling ln pot culture was subjected to soi! drench with a solution of the compound of Formula (I), which had been prepared so as to be a 10% acetone water.

Three days after the treatment, ten second instar larvae of Nilaparvata lugens, which had been coliected outdoors and proliferated indoors, were each released to the rice seedling. Thereafter, the larvae were left to stand ln a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25°C. Six days after the release, the larvae were observed for survival or death, and the mortality of larvae was calculated by the 10 following équation. Test in dupllcate.

Mortality of larvae (%) - (number of dead larvae/(number of survived larvae + number of dead larvae)} χ 100

Furthermore, for comparlson, the test against a species of Nilaparvata lugens which is highly susceptible to imidacloprid was performed by the same method as described above, and the results thereof are shown in Table 45. As described in Table

45, Compound P212 and Compound 1-20 exhibited high insectiddal effects against susceptible species and drug résistant species of Nilaparvata lugens, and the death rates of larvae at 0.005 mg/seedling were (susceptible species) 100% and 100%,

286 (résistant population I) 95% and 77% and (résistant population II) 100% and 85%, respectively. Meanwhile, the death rates of imidacloprid at 0.05 mg/seediing were (susceptible species) 100%, (résistant population I) 38% and (résistant population II) 69%, and the insecticidal effect thereof was also low even at a high dose. From the above results, it became obvious that Compound P212 and Compound 1-20 hâve high Insecticidal effects even against Nilaparvata lugens résistance against imidacloprid.

Further, for the origln of test pests, bugs collected outdoors from the Kumamoto préfecture (I) In 2007 and from the Fukuoka préfecture (II) in 2005 as résistant population of Nilaparvata lugens, and bugs collected from the Kagoshima préfecture and then successively reared indoors for a long time as the imidacloprid susceptible population of Nilaparvata lugens were used.

[Table 56]

Insecticidal effects against Nilaparvata lugens (death rate %)

	Throughp ut (mg/seedl Ing)	Effects against Nilaparvata lugens
Susceptible population	Résistant population 1	Résistant population II
six days after the treatment	six days after the treatment	six days after the treatment
P212	0.05	100	100	100
0.005	100	95	100
1-20	0.01	95	100	100
0.005	100	77	85
Imidacloprid	0.05	100	38	69
0.01	100	39

Test Example 1 Soil Irrigation Treatment Test of Laodelphax striatella

A rice seedling in pot culture was subjected to soil drench treatment with a dru g solution of the compound of Formula (I) at a predetermined concentration, or a drug solution of a mixture of a compound of Formula (I) and an insecticide as indicated below at a predetermined concentration, which had been prepared so as to be a 10% acetone water. After the rice seedling was left to stand for 3 days, second instar

287 l I7n î U» , ₍ larvae were released thereto. Thereafter, the larvae were left to stand ln a thermostatic chamber (16 hours of light perîod-8 hours of dark period) at 25°C. Three days after the release, the larvae were observed for survival or death, and the mortality of larvae was calculated by the following équation. The test was performed in duplicate.

Mortality of larvae (%) = {number of dead iarvae/(number of survived larvae + number of dead larvae)} x 100 ln addition, when there was no synergistic effect, a theoretical value was calculated by the Colby*s équation shown as follows, and the results are shown in the Table.

Colb/s équation: theoretical value (%) - 100 - (A x B)/100 (A: 100 - (mortality of larvae or adults when treated only with Compound P212 or Compound 1-20)

B: 100 - (mortality of larvae or adults when treated only with each of imidacloprid, fipronil, chlorantraniliprole, spinosad, clothianidin, dinotefuran, sutfoxaflor, pymetrozine, Ihiamethoxam, flupyradifurone and cycloxaprîd))

Method for judging synergistic effects

When the mortality against Laodelphax striatella in the case of a mixture with another agent exceeded the theoretical value by the Colb/s équation, a synergistic effect was judged to be présent.

It was demonstrated thaï mixed agente of the Insecticides of imidacloprid, fipronil, chlorantraniliprole, spinosad, clothianidin, dinotefuran, sutfoxaflor, pymetrozine, thiamethoxam, flupyradifurone and cycoxaprid, which were provided and tested as Compound P212, ail show a mortality of larvae or adulte, exceed the theoretical value and hâve synergistic effects.

ln addition, it was demonstrated that mixed agente of the Insecticides of

288

5i ' 'Ί' · l ' ’ Ml imidacloprid and fipronil, which were provided and tested as Compound 1-20, ail show a mortality of larvae or adults, exceed the theoretical value and hâve synergistic effects.

Furthermore, it was demonstrated that mixed agente of the fongicides of probenazole, Isotianil, tiadinil and orysastrobln, which were provided and tested as

Compound P212, ail exhibit Insecticidal effect equal to or higher than the insecticidal effect when treated with Compound P212 atone and may be mixed and treated with a fongicide. Likewise, it was demonstrated that mixed agents of the fongicide of probenazole, which was provided and tested as Compound 1-20, exhibit insecticidal effect equal to or higher than the insecticidal effect when treated with Compound 1-20 o atone and may be mixed and treated with a fongicide.

<Example of mixed agent with insecticide» [Table 5η

Mortality (%) of single agent and mixed agent against Laodelphax striatella

Insecticide name	Rate	Compound P212
mg/ Seedllng	0	0. 005
-	-	0	39
Imidacloprid	0. 005	0	70
Fipronil	0. 005	26	65
Chlorantranillprole	0. 05	9	60
Spinosad	0. 5	0	62

[Table 58]

Theoretical value (%) by Colb/s équation

Insecticide name	Rate	Compound P212
mg/ Seedling	0	0. 005
-	-	0	39
Imidacloprid	0. 005	0	39

289 , ο n -r i

Fipronil	0. 005	26	55
Chlorantranlllprole	0. 05	9	44
Splnosad	0. 5	0	39

[Table 59]

Mortality (%) of single agent and mixed agent against Laodelphax striatella

Insecticide name	Rate	Compound P212
mg/ Seedllng	0	0. 005
-	-	0	18
Clothlanidin	0. 005	23	56
Dlnotefuran	0. 005	0	30
Sulfoxaflor	0. 005	1	63
Pymetrozine	0. 05	15	89

[Table 60]

Theoretlcal value (%) by Colb/s équation

Insecticide name	Rate	Compound P212
mg/ Seedllng	0	0. 005
-	-	0	18
Clothlanidin	0. 005	23	37
Dlnotefuran	0. 005	0	18
Sulfoxaflor	0. 005	1	19
Pymetrozine	0. 05	15	30

[Table 61]

Mortality (%) of single agent and mixed agent against Laodelphax striatella

Insecticide name	Rate	Compound P212
mg/ Seedllng	0	0. 005
-	-	0	14

290

Thlamethoxam 0. 01 23 45 [Table 62]

Theoretical value (%) by Colb/s équation

Insecticide name	Rate	Compound P212
mg/ Seedling	0	0. 005
-	-	0	14
Thlamethoxam	0. 01	23	34

[Table 63]

Mortality (%) of single agent and mlxed agent against Laodelphax striatella

Insecticide name	Rate mg/ Seedling	Compound P212
0	0. 005
-	-	0	45
Flupyradifurone	0. 01	5	85

[Table 64]

Theoretical value (%) by Colb/s équation

Insecticide name	Rate mg/ Seedling	Compound P212
0	0. 005
-	-	0	45
Flupyradifurone	0. 01	5	48

[Table 65]

Mortality (%) of single agent and mixed agent against Laodelphax striatella

Insecticide name	Rate mg/ Seedling	Compound 1-20
0	0. 005
-	-	0	12
Imidacloprid	0. 005	0	74
Fipronil	0. 001	0	80

[Table 66]

Theoretical value (%) by Colb/s équation

Insecticide name	Rate mg/ Seedling	Compound 1-20
0	0. 005
-	-	0	12

291 •H J \ ‘1 t *1' · ]

Imidacioprid	0. 005	0	12
Fipronil	0. 001	0	12

[Table 67]

Mortality (%) of single agent and mixed agent against Laodeiphax striatella

Insecticide name	Rate	Compound P212
mg/ Seedling	0	0. 005
-	-	0	0
Cycioxaprid	0. 005	0	7

[Table 68]

Theoretical value (%) by Colb/s équation

Insecticide name	Rate	Compound P212
mg/ Seedling	0	0. 005
>	-	0	0
Cycioxaprid	0. 005	0	0

[Table 69]

Mortality (%) of single agent and mixed agent against Laodeiphax striatella

Funglclde name	Rate	Compound P212	Compound 1-20
mq/ Seedling	0	0. 005	0	0. 005
-	-	0	39	0	8
Probenazole	0. 5	9	59	9	65

[Table 70]

Theoretical value (%) by Colb/s équation

Fungiclde name	Rate	Compound P212	Compound 1- 20
mg/ Seedling	0	0. 005	0	0. 005
-	-	0	39	0	8
Probenazole	0. 5	9	44	9	16

[Table 71]

Mortality (%) of single agent and mixed agent against Laodeiphax striatella

292

Fungicide name	Rate	Compound P212
mg/ Seedling	0	0. 005
-	-	0	19
Isotianil	0. 5	5	30
Tladinil	0. 5	8	30
Orysastrobln	0. 5	4	70

[Table 72]

Theoretical value (%) by Coiby*s équation

Fungicide name	Rate	Compound P212
mg/ Seedling	0	0. 005
-	-	0	19
Isotianil	0. 5	5	23
Tladinil	0. 5	8	25
Orysastrobln	0. 5	4	22

Test Example 2 Foiiar treatment test against Laodelphax striatella

A drug solution of the compound of Formula (I) at a predetermined concentration, or a drug solution of a mixture of a compound of Formula (I) and an Insecticide as Indicated below at a predetermined concentration, which had been prepared so as to be a 50% acetone water (0.05% Tween20 available), was foiiar sprayed to a rice seedling in pot culture. After an air drying process, second instar larvae were released thereto. Thereafter, the larvae were left to stand In a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25°C. Three days after the reiease, the larvae were observed for survival or death, and the mortality of larvae was calculated by the following équation. The test was performed in duplicate.

Mortality of larvae (%) = (number of dead larvae/(number of survived larvae + number of dead larvae)} x 100

Further, when there was no synergistic effect, a theoretical value was calculated by the Colb/s équation shown as foliows, and the results are shown in the Table.

Colb/s équation: Theoretical value (%) = 100 - (Αχ B)/100 (A: 100 - (mortality of larvae or adults when treated only with Compound P212 or Compound 1-20)

293

Γ i 7li 11 < t. 1 1

B: 100 - (mortality of larvae or adults when treated only with etofenprox or silafluofen))

Method for judging synergistic effects

When the mortality against Laodelphax striatella In the case of a mixture with another agent exceeded the theoretical value by the Coiby*s équation, a synergistic effect was judged to be présent.

It was demonstrated that mixed agents of the insecticides of etofenprox and silafluofen, which were provided and tested as Compound P212 or Compound 1-20, ail show a mortality of larvae or adults approximately equal to the theoretical value, and may be mixed with the insecticide even in a foliar treatment-like usage.

[Table 73]

Mortality (%) of single agent and mixed agent against Laodelphax s striatella

Insecticide name	Rate (ppm)	-	Compound P212	Compound 1- 20
0	0. 625	0. 625
-		0	95	90
Etofenprox	10	30	90	95
Silafluofen	5	55	100	100

[Table 74]

Theoretical value (%) by Colb/s équation

Insecticide name	Rate (ppm)	-	Compound P212	Compound ΙΣΟ
0	0.625	0. 625
		0	95	90
Etofenprox	10	30	97	93
Silafluofen	5	55	98	95

Test Example 3 Pest control test of Aphis gossypli

A leaf disk having a diameter of 2.0 cm was eut out from a cucumber ln pot culture, and a drug solution of the compound of Formula (I) at a predetermined concentration, or a drug solution of a mixture of a compound of Formula (I) and an Insecticide as indlcated below at a predetermined concentration, which had been

294 prepared so as to be a 50% acetone water (0.05% Tween20 available), was sprayed thereto. After an air drying process, first Instar larvae were released thereto. Thereafter, the larvae were left to stand In a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25°C. Three days after the release, the larvae were observed for survival or death, and the mortality of larvae was calculated by the following équation. The test was performed in duplicate.

Mortality of larvae (%) s (number of dead larvae/(number of survived iarvae + number of dead larvae)) x 100

In addition, when there was no synergistic effect, a theoretical value was calculated by the Colb/s équation shown as follows, and the results are shown in the Table.

Colb/s équation: Theoretical value (%)- 100- (Αχ ByiOO (A: 100 - (mortality of iarvae or adults when treated only with Compound P212 or Compound 1-20)

B: 100 - (mortality of larvae or adults when treated only with afidopyropen) Method for judging synergistic effects

When the mortality against Aphis gossypii in the case of a mixture with another agent exceeded the theoretical value by the Colb/s équation, a synergistic effect was judged to be présent.

It was demonstrated that mixed agents of compounds of Formula (II), which were provided and tested as Compound P212 or Compound 1-20, ali show a mortality of iarvae or adults, exceed the theoretical value and hâve synergistic effects.

[Table 75]

Mortality (%) of single agent and mixed agent against Aphis gossypii

Insecticide name	Rate	Compound P212	Compound 1-20
ppm	0	0. 313	0	0. 625
-	-	0	45	0	19

295

Afidopyropen

0. 002 (Table 76]

Theoretical value (%) by Colby*s équation

Insecticide name	Rate	Compound P212	Compound 1-20
ppm	0	0. 313	0	0. 625
-	-	0	45	0	19
Afidopyropen	0. 002	25	59	25	39

Test Example 4 Pest control test of Plutella xvlostella

A leaf disk having a diameter of 5.0 cm was eut out from a cabbage ln pot culture, and a drug solution of the compound of Formula (!) at a predetermined concentration, or a drug solution of a mixture of a compound of Formula (I) and an Insecticide as indicated below at a predetermined concentration, which had been prepared so as to be a 50% acetone water (0.05% Tween20 available), was sprayed thereto. After an air drying process, second instar larvae were released thereto. Thereafter, the larvae were left to stand ln a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25°C. Three days after the reiease, the larvae were observed for survival or death, and the mortality of larvae was calculated by the foliowing équation. The test was performed ln dupiicate.

Mortality of larvae (%) » (number of dead larvae/(number of survived larvae + number of dead larvae)} χ 100

Furthermore, when there was no synergistic effect, a theoretical value was calculated by the Colby*s équation shown as follows, and the results are shown in the Table.

Colb/s équation: Theoretical value (%) = 100 - (A x By 100 (A: 100 - (mortality of larvae or adults when treated with only Compound P212)

B: 100 - (mortality of larvae or adults when treated with only

296 flometoquln, spinosad, fipronil, chlorantranlllprole, 1-((6-chloropyrldin-3yl)methyl)-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimidin-1-1um-2-olate, or afidopyropen))

Method for judging synergîstic affects

When the mortality against Piutella xylostella In the case of a mixture with another agent exceeded the theoretlcai value by the Colby's équation, a synergîstic effect was judged to be présent.

It was demonstrated that a mixed agent of the Insecticide of flometoquln, which was provided and tested, with Compound P212, shows a death rate of larvae or adults, 10 exceeds the theoretical value and has synergîstic effects.

[Table 77}

Mortality (%) of single agent and mixed agent against Piutella xylostella

Insecticide name	Rate	Compound P212
ppm	0	1. 25
-	-	0	0
Flometoquln	0. 313	0	30

[Table 78]

Theoretical value (%) by Colby's équation

Insecticide name	Rate	Compound P212
ppm	0	1. 25
-	-	0	0
Flometoquln	0. 313	0	0

[Table 79]

Mortality (%) of single agent and mixed agent against Piutella

^îsectÎdde^îame ' ~~ ' —	ppm
0	1.0
—	0	40
Afidopyropen	Rate	10	20	70
Splnosad	ppm	0.01	11	70

[Table 80)

Theoretical value (%) by Colby's équation

Insecticide name	Compound P212
Rate ppm
0	1.0
—	0	40
Afidopyropen	Rate	10	20	52
Splnosad	ppm	0.01	11	45

[Table 81]

Mortality (%) of single agent and mixed agent against Piutella xylostella

.....: i t

298

Insecticide namë _
—	0	30
Afldopyropen	Rate ppm	5	0	80

[Table 82]

Theoretical value (%) by Colby's équation

Insecticide name	Compound P212
Rate ppm
0	1.0
—	0	30
Afidopyropen	Rate PPm ’	5	0	30

[Table 83]

Mortality (%) of single agent and mixed agent against Plutella xylostella

299 • ill

—	0	60
Fipronil	Rate	0.04	50	100
Chlorantranlllprole	ppm	0.002	60	100

[Table 84)

Theoretical value (%) by Colby's équation

Insecticide name	Compound P212
Rate ppm
0	2.0
—	0	60
Fipronil	Rate	0.04	50	80
Chlorantranlllprole	ppm	0.002	60	84

[Table 85]

Mortallty (%) of single agent and mixed agent against Plutella xylostella

Insecticide name	Compound P212
Rate ppm
0	2.0
—	0	50
1-((6-chloropyridln-3-	Rate	1	30	70

300 ’ ·· *......i

yl)methyl)-4-oxo-3phenyl-4H-pyrldo[1,2a]pyrlmldin-1-ium-2olate	ppm
Afldopyropen	5	0	100

[Table 86]

Theoretlcal value (%) by Colby's équation

Insecticide name	Compound P212 Rate PPm
0	2.0
—	0	50
1-((6-chioropyridin-3yl)methyl)-4-oxo-3phenyl-4H-pyrido[1,2a]pyrlmidin-1-lum-2olate	Rate PPm	1	30	65
Afldopyropen	5	0	50

Test Example 5 Pest control test of Spodoptera litura

A leaf disk having a diameter of 5.0 cm was eut out from a cabbage ln pot culture, and a drug solution of the compound of Formula (I) at a predetermined concentration, or a drug solution of a mixture of a compound of Formula (I) and an Insecticide as Indicated below at a predetermined concentration, which had been prepared so as to

301 be a 50% acetone water (0.05% Tween20 availabie), was sprayed thereto. After an air dryîng process, third instar larvae were released thereto. Thereafter, the larvae were left to stand In a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25°C. Three days after the release, the larvae were observed for survlval or death, and the larvae mortality was calculated by the following équation. The test was performed in duplicate.

Mortality of larvae (%) = {number of dead larvae/(number of survlved larvae + number of dead larvae)) χ 100

Furthermore, a theoretical value for the case of no synergistic effect was calculated using Colb/s équation given below, and the results are shown in the tables.

Colb/s équation: Theoretical value (%) = 100 - (A χ B)/100 (A: 100 - (mortality of larvae or adults when treated only with Compound P212)

B: 100 - (mortality of larvae or adults when treated with only the insecticide chlorantraniliprole, emamectin benzoate, flometoquin, or afidopyropen))

Method for judging synergistic effects

When the mortality against Spodoptera litura in the case of a mixture with another agent exceeded the theoretical value given by Colb/s équation, a synergistic effect was judged to be présent.

It was demonstrated that a mixed agent of the insecticide chlorantraniliprole, emamectin benzoate, flometoquin, or afidopyropen tested with Compound P212 shows a mortality for larvae or adults in excess of the theoretical value and has synergistic effects.

[Table 87]

Mortality (%) of single agent and mixed agent against Spodoptera litura (1)

302

I

Insecticide name	Compound P212
Rate ppm
0	20
—	0	40
Afidopyropen	Rate ppm	10	0	80

[Table 88]

Theoretical value (%) by Colby's équation

Insecticide name	Compound P212
Rate ppm
0	20
—	0	40
Afidopyropen	Rate ppm	10	0	40

[Table 89]

Mortality (%) of single agent and mixed agent against Spodoptera

kisectlcIde^Îame^^'	ppm
0	20
—	0	10
Chlorantranlllprole	Rate	0.02	20	30
Emamectin benzoate	ppm	0.02	0	20

[Table 90]

Theoretical value (%) by Colby's équation

Insecticide name	Compound P212
Rate ppm
0	20
—	0	10
Chlorantranlllprole	Rate	0.02	20	28
Emamectin benzoate	ppm	0.02	0	10

304 [Table 91]

Mortality (%) of single agent and mlxed agent against Spodoptera lltura (3)

Insecticide name	Compound P212
Rate ppm
0	50
—	0	10
Flometoquin	Rate	5	10	20
Afidopyropen	ppm	5	0	50

[Table 92]

305 • ¹ > D \ '1, | '

Flometoquin	Rate	5	10	19
Afidopyropen	Ppm	5	0	10

Test Example 6 Pest control test of Frankliniella occidentalis

A leaf disk having a diameter of 2.8 cm was eut out from the common bean in pot culture, and a drug solution of the compound of Formula (I) at a predetermined concentration, or a drug solution of a mixture of a compound of Formula (I) and an Insecticide as indicated below at a predetermined concentration, which had been prepared so as to be a 50% acetone water (0.05% Tween20 available), was sprayed thereto. After an air drying process, first instar larvae were released thereto. Thereafter, the larvae were left to stand In a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25°C. Three days after the release, the larvae were observed for survival or death, and the larvae mortality was calculated by the following équation. The test was performed In duplicate.

Mortality of larvae (%) = (number of dead larvae/(number of survived larvae + number of dead larvae)) χ 100

Furthermore, a theoretical value for the case of no synergistic effect was calculated using Colb/s équation glven below, and the results are shown In the table.

Colb/s équation: Theoretical value (%) = 100 - (A χ B)/100 (A: 100 - (mortality of larvae or adults when treated only with Compound P212) B: 100 - (mortality of larvae or adults when treated with only the insecticide

306

Γ ,ït 11 7b ()\ 9 i ’ '1' 1 imidacloprid, dinotefuran, or acetamiprid))

Method for judging synergistic effects

When the mortality against Frankliniella occidentalis ln the case of a mixture with another agent exceeded the theoretical value given by Colb/s équation, a synergistic 5 effect was judged to be présent.

It was demonstrated that a mixed agent of the insecticide imidacloprid or dinotefuran tested with Compound P212 shows a mortality for larvae or adults in excess of the theoretical value and has synergistic effects.

[Table 93]

Mortality (%) of single agent and mixed agent against Frankliniella occldentalls(l)

Insecticide name	Compound P212
Rate ppm
0	10
—	0	69
Imidacloprid	Rate ppm	20	69	94

[Table 94]

307

^nsecfldde^Îame^ ' ’ —--------~	0	10
—	0	69
Imldacloprid	Rate ppm	20	69	90

[Table 95]

Mortallty (%) of single agent and mlxed agent against Frankllnlella occldentalls(2)

Insecticide	Compound P212
Rate PPm
0	20
—	0	70
Dlnotefuran	Rate ppm	5	35	85

[Table 96]

308

—	0	70
Dinotefuran	Rate ppm	5	35	81

Test Example 7 Soll Irrigation treatment test on Chilo suppressalis

Rice seedlings ln pot culture were submitted to a soll Irrigation treatment with a drug solution of the compound of Formula (I) at a predetermined concentration, or a drug solution of a mixture of a compound of Formula (I) and an insecticide as indicated below at a predetermined concentration, which had been prepared so as to be a 10% acetone water. After standing for 3 days, second instar larvae were released thereto. This was followed by standing in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25°C. Six days after the release, the larvae were observed for survival or death, and the larvae mortality was calculated by the following équation. The test was performed ln duplicate.

Mortality of larvae (%) = {number of dead larvae/(number of survived larvae + number of dead larvae)} χ 100

Furthermore, a theoretical value for the case of no synergistic effect was calculated using Colby*s équation given below, and the results are shown ln the table.

Col b/s équation: Theoretical value (%) = 100 - (A x B)/100 (A: 100 - (mortality of larvae or adults when treated only with Compound P212) B: 100 - (mortality of larvae or adults when treated with only the insecticide fipronil, cyantranlllprole or splnosad))

Method for judging synergistic effects

When the Insecticidal effect (table) against Chilo suppressalis in the case of a mixture with another agent exceeded the theoretical value given by Colb/s équation, a synergistic effect was judged to be présent.

309 .jlll''¹'· i

It was demonstrated that a mixed agent of the Insecticide fipronil, cyantraniliprole or spinosad tested with Compound P212 shows a mortality for larvae or adults In excess of the theoretical value In both cases and has synergistic effects.

[Table 97]

Mortality (%) of single agent and mixed agent against Chllo suppressalls(l)

Insecticide name	Compound P212
Rate mg/seedllng
0	0,01
—	0	33
Cyantraniliprole	Rate mg/seedling	0.005	83	100

[Table 98]

Theoretical value (%) by Colby's équation

Insecticide name	Compound P212
Rate mg/seedllng
0	0.01
—	0	33
Cyantraniliprole	Rate mg/seedllng	0.005	83	89

310 ’ > J'J.l [Table 99]

Mortallty (%) of single agent and mixed agent against Chilo suppressalis(2)

1 nseetic 1 de	Compound P212
Rate mg/seedling
0	0.002
—	0	40
Fipronil	Rate mg/seedllng	0.0005	40	80
Chlorantraniliprole	0.0005	60	80
Spinosad	0.002	80	100

[Table 100]

Theoretical value (%) by Colby’s équation

Insecticide name	Compound P212
Rate mg/seedling
0	0.002
—	0	40
Fipronil	Rate mg/seedling	0.0005	40	64
Chlorantranlllprole	0.0005	60	76
Spinosad	0.002	80	88

Test Exemple 8 Soil Irrigation treatment test on Naranqa aenescens

Rice seedlings in pot culture were subjected to a soil irrigation treatment with a

311 drug solution of the compound of Formula (I) at a predetermined concentration, or a drug solution of a mixture of a compound of Formula (I) and an insecticide as indicated below at a predetermined concentration, which had been prepared so as to be a 10% acetone water. After standing for 3 days, first instar larvae were released thereto. This was followed by standing in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25°C. Five days after the release, the larvae were observed for survival or death, and the larvae mortality was calculated by the following équation. The test was performed in duplicate.

Mortality of larvae (%) = {number of dead larvae/(number of survlved larvae + number of dead larvae)} x 100

Furthermore, a theoretical value for the case of no synergistic effect was calculated using Colb/s équation given below, and the results are shown in the table.

Colb/s équation: Theoretical value (%) = 100 - (A χ B)/100 (A: 100 - (mortality of larvae or adults when treated only with Compound P212) B: 100 - (mortality of larvae or adults when treated with only the insecticide spinosad or fîpronil))

Method for judglng synergistic effects

When the mortality against Naranga aenescens In the case of a mixture with another agent exceeded the theoretical value given by Colb/s équation, a synergistic effect was judged to be présent.

It was demonstrated that a mixed agent of the Insecticide spinosad or fîpronil tested with Compound P212 shows a mortality for larvae or adults in excess of the theoretical value In ail cases and has synergistic effects.

312 [Table 101]

Mortality (%) of single agent and mixed agent against Naranga aenescens

Insecticide name	Compound P212
Rate mg/seedllng
0	0.01
—			0	60
Splnosad	Rate	0.005	40	100
Fipronil	mg/seedllng	0.01	20	80

[Table 102]

Theoretical value (%) by Coiby’s équation

Insecticide name	Compound P212
Rate mg/seedllng
0	0.01
—			0	60
Splnosad	Rate	0.005	40	76
Fipronil	mg/seedllng	0.01	20	68

313

Test Example 9 Test on Callosobruchus chinensîs

A compound of Formula (I) and the insecticide Indicated below, prepared in predetermined concentrations using acetone, were separateiy toplcally applied to the back of the same adult Callosobruchus chinensîs. The Callosobruchus chinensîs was then Introduced Into a plastic cup and held in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25°C. One day after the reiease, the insects were observed for survival or death, and the insect mortality was calculated by the following équation. The test was performed in duplicate.

Insect mortality (%) = (number of dead insects/(number of survived insects + number of dead insects)} x 100

Furthermore, a theoretical value for the case of no synerglstic effect was calculated using Colby*s équation given below, and the results are shown in the table.

Colby*s équation: Theoretical value (%) = 100 - (Αχ BJ/100 (A: 100 - (insect mortality for treatment with only Compound P212)

B: 100 - (insect mortality for treatment with only the Insecticide fipronil or imldacioprid))

Method forjudging synergistic effects

When the mortality against Callosobruchus chinensîs in the case of a mixture with another agent exceeded the theoretical value given by Colb/s équation, a synergistic effect was judged to be présent.

It was demonstrated that co-treatment with the insecticide fipronil or imldacioprid tested with Compound P212 shows an insect mortality in excess of the theoretical value ln both cases and has synergistic effects.

[Table 103]

Mortality (%) of single agent and mlxed agent against Callosobruchus chinensis

314 . f | i

J ' l

Insecticide name	Compound P212
Rate ng/head
0	0.2
—			0	20
Fipronil	Rate	0.2	0	36
Imidacloprid	ng/head	0.2	40	60

[Table 104]

Theoretical value (%) by Colby's équation

Insecticide name	Compound P212
Rate ng/head
0	0.2
—			0	20
Fipronil	Rate	0.2	0	20
Imidacloprid	ng/head	0.2	40	52

Test Exampie 10 Pest control test of Rlce blast

A rice seedling In pot culture was subjected to soi! Irrigation treatment with a drug solution of the compound of Formula (I) at a predetermined concentration, or a drug , ,’it;.......i- i ··*') 1

315 solution of a mixture of a compound of Formula (I) and an insecticide as Indicated below at a predetermined concentration, which had been prepared with a 10% acetone water. Three days after the treatment, a spore suspension (2 χ 10⁵ ea/mL, 0.05% Tween avallable) of rice blast bacteria was sprayed and Inoculated thereto, and the rice 5 seedling was placed In a molst chamber for 24 hours to promote Infection. Thereafter, the larvae were left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25°C. Seven days after the Inoculation, the number of lésions was measured, and the préventive value was calculated by the following équation. The test was performed In triplicate.

Préventive value = {(number of lésions in a zone without treatment - number of lésions In a zone with treatment)/(number of lésions without treatment)} χ 100 As a resuit, it was demonstrated that in a throughput of probenazole at 0.125 mg/ seedling, any one mixed agent of Compound P212 and Compound 1-20 exhtbtts insecticidal effect equal to the insecticidal effect when treated with probenazole alone 15 and may be mixed and treated with a fongicide.

[Table 105]

Insecticide name	Compound P212	Compound 1-20
Rate mg/seedllng
0	2.5	0	2.5
—	0	3.3	0	52.5
Probenazole	Rate mg/seedllng	0.125	96.7	93.4	96.7	91.8

Test Exampie 11 Test of rice blast control (foliar treatment)

316 , l I I 7ll l) ' Ί- · ‘ >’

Rico seedlings were treated by foliar application with a drug solution of the compound of Formula (I), or a drug solution of a mixture of a compound of Formula (I) and the fungicide Indicated below, prepared In a predetermined concentration with 10% acetone water. After the treatment, a rice blast spore suspension (1.5 χ 10⁵ ea/mL, 0.05% Tween available) was sprayed and inoculated thereto followed by holding in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25°C. Fourteen days after the inoculation, the number of lésions was measured, and the préventive value was calculated by the following équation. The test was performed in triplicate.

Préventive value = {(number of lésions In a zone without treatment - number of lésions in a zone with treatment)/(number of lésions In a zone without treatment)} x 100

As a resuit, it was demonstrated that at a treatment concentration of 0.5 ppm using tiadinil, isotianil, orysastrobin, tricyclazole, diclocymet, tebufloquin, azoxystrobin or kasugamycin, the mixed agent with Compound P212 also exhibits a fungicidal effect equal to that for treatment with tiadinil, isotianil, orysastrobin, tricyclazole, diclocymet, tebufloquin, azoxystrobin or kasugamycin alone and a mixed treatment with a fungicide is therefore possible.

[Table 106]

—	0	4
Tiadinll	Rate	0.5	0	18
Isotianil	PPm	0.5	66	72

[Table 107] (Rlce blast test 2)

Fungicide name	Compound P212
Rate PPm
0	50
—	0	16
Orysastrobin		0.5	20	91
Tricyclazole	Rate	0.5	72	92
Dlclocymet	ppm	0.5	8	52
Tebufloquin		0.5	48	72

[Table 108] (Rico blast test 3)

Fungicide name	Compound P212
Rate ppm
0	50
—	0	0
Azoxystrobin	Rate	0.5	37	35
Kasugamycin	ppm	0.5	0	37

318

Test Example 12 Testofcontroloffice sheath blight (Rhlzoctonia solanO

Six weeks after planting, rice seedlings were subjected to foliar spray treatment with a drug solution of the compound of Formula (I), or a drug solution of a mixture of a compound of Formula (I) and a fongicide as Indicated below, prepared In a predetermined concentration with 10% acetone water. After an air drying process, a plug of growing Rhizoctonla solani (1.0 cm² agar square each) was allowed to stand at the base of the rice. This was followed by holding In a thermostatic chamber (30°C day-25°C nig ht, 16 hours of light period-8 hours of dark period). Six days after the Inoculation, the lésion height was measured, and the préventive value was calculated by the following équation. The test was performed in duplicate.

Préventive value = ((lésion height in a zone without treatment - lésion height in a zone with treatment)/(lesion height in a zone without treatment)} χ 100

As a resuit, it was demonstrated that, at a treatment concentration of 5 ppm using thifluzamlde, furametpyr, pencycuron, azoxystrobin, simeconazole, valldamycln, or orysastrobln, the mixed agent with 50 ppm Compound P212 presented the same funglcldal effect as for treatment with thifluzamlde, furametpyr, pencycuron, azoxystrobin, simeconazole, valldamycln, or orysastrobln alone, and mixed treatment with a fongicide ls therefore possible.

[Table 109]

Funglcide name	0	50
—	0	14
Thifluzamide	Rate ppm	5	92	97
Furametpyr	5	77	94
Pencycuron	5	69	77

[Table 110] (Sheath bilght test 2)

Funglcide name	Compound P212
Rate ppm
0	50
—	0	9
Azoxystrobln		5	95	100
Slmeconazole	Rate	5	5	24
Vaiidamycin	PPm	5	32	74
Orysastrobln		5	72	59

Test Example 13 Test with Laodelphax striatellus bv treatment during the végétative phase

Rlce was planted In nursery boxes and emergence was carried out for three days a 30°C followed by transfer of the nursery boxes to a glass greenhouse at 25°C. During the végétative phase five days after planting, the nursery boxes were treated 10 with a prescribed amount of a mixed granule of 0.24 mg/mg probenazole (24%) and

0.02 mg/mg Compound P212 (2%). The rice seedlings were transplanted to 1/5000a » V I V'il 1

320

Wagner pots 22 days after planting and were grown in a greenhouse at 25°C. Second Instar larvae of Laodelphax striatellus were released at 13,26, and 38 days posttransplantation to the Wagner pots; this was followed by holding ln a glass greenhouse at 25°C. Five days after the release, the larvae were observed for survival or death, and the larvae mortality was calculated by the following équation. The test was performed ln duplicate.

Mortality of iarvae (%) - (number of dead larvae/fnumber of survlved larvae + number of dead larvae)) x 100

According to the results, It was shown that the mixed granule of probenazoie and Compound P212 presented a high Insectlcldal effect of 100% mortality and exhiblted control at a practlcal level.

Test Example 14 Test with Laodelphax striatellus by soll Irrigation treatment

Rico seedlings ln pot cultivation were subjected to a soil Irrigation treatment with a drug solution of a compound of Formula (I) or a drug solution of a mixture of a compound of Formula (i) and a paddy herbicide as indicated below, prepared ln predetermined concentrations so as to be a 10% acetone water. After standing for three days, second instar larvae were released thereto. Thereafter, the iarvae were left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25°C. five days after the release, the iarvae were observed for survival or death, and the larvae mortality was calculated by the following équation. The test was performed ln duplicate.

Mortality of larvae (%) = (number of dead larvae/(numberof survived larvae + number of dead iarvae)} χ 100

The mixed agent of Imazosulfuron, cafenstrole, cyhalofop-butyl, daimuron and

321

U v t, pyrazolate tested with the Compound P212 was shown ln ail instances to exhibit an insecticldal effect at least equal to that for treatment with Compound P212 by itself, and a mixed treatment with a herbicide Is thus possible.

[Table 111]

Herbicide name	Compound P212
Rate mg/seedling
0	0.005	0.01
—	0	0	100
Imazosulfuron		0.05	0	0	100
Cafenstrole	Rate mg/seedling	0.05	0	0	100
Cyhalofop-butyl	0.05	0	0	100
Daimuron	0.05	0	0	100
Pyrazolate		0.05	0	0	100

Test Example 15 Test of the control of Haemaphvsalis lonoicomis

A capsule with a diameter of 2 cm and a height of 2 cm was attached to the dorsal surface of a mouse. A compound of Formula (I), ivermectin, moxldectin, permethrin, amltraz, fipronil, splnetram and the mixture of the compound of Formula (I) 10 and each Insecticide were dissolved ln éthanol at the concentrations given in Table O, and each of these was dripped onto the surface of a mouse body within a capsule. After thorough drying, eight Haemaphysalis longlcomis nymphs were released and the top of the capsule was sealed with a lid. The mouse was kept in a cage at 25°C using a 12-hour light period and a 12-hour dark period. Five days after the reiease, the capsule was removed and the number of surviving and dead nymphs and the number

322 il π n v » ]_>i i i of engorged individuels were counted and the Insect mortality and agonal rate was calculated by the following équation.

Insect mortality and agonal rate (%) = {number of dead and agonal lnsects/(number of survived insects + number of dead and agonal Insects)) x 100 5 The results showed that, at a rate of 0.009 pg of Ivermectin or moxldectln, the mixed agent of either with Compound P212 also gave a tick control effect that was the same as treatment with Ivermectin, moxldectin, permethrin, amitraz, fipronil and spinetram alone and mixed treatment with ivermectin, moxidectln, permethrin, amitraz, fipronil and spinetram Is thus possible.

fiable 112]

Mortality (%) of single agent and mixed agent against

Haemaphysalls longlcornls(1 )

insecticide name	Compound P212
Rate M9
0	1.18
—	0	53
Ivermectin	Rate	0.009	3	53
Moxldectln	M9	0.009	6	44

[Table 113]

Mortallty (%) of single agent and mixed agent against

Haemaphysalls longlcornls(2)

323

Insecticide	Compound P212
Rate pg
0	1.18
—	0	60
Amitraz	Rate	0.38	41	90
Permethrin	pg	9.5	71	86

[Table 114]

Theoretical value (%) by Colby's équation

Insecticide name	Compound P212
Rate pg
0	1.18
—	0	60
Amitraz	Rate	0.38	41	77
Permethrin	pg	9.5	71	88

[Table 115]

Mortality (%) of single agent and mixed agent against

Haemaphysalis longlcornls(3)

324 ’ 1171 » U X ^: 17 ί l^J ' » ,

Insecticide name	Compound P212
Rate pg
0	1.18
—	0	38
fîpronil	Rate	0.38	78	93
spinetoram		0.38	6	22

[Table 116]

Theoretical value (%) by Colby's équation

Insecticide name	Compound P212
Rate pg
0	1.18
—	0	38
fipronll	Rate	0.38	78	86
spinetoram	pg	0.38	6	41

[Table 117] ’>l 117 <’> \ 47

Mortality (%) of single agent and mixed agent against

Haemaphysalis longicornis(4)

325

Insecticide name	Compound P212
Rate pg
0	1.18
—	0	18
pyrlproxyfen	Rate	0.0475	2	44
spinosad	pg	1.9	2.5	43

[Table 118J

Theoretical value (%) by Colby's équation

Insecticide name	Compound P212
Rate pg
0	1.18
—	0	18
pyrlproxyfen	Rate	0.0475	2	20
spinosad	pg	1.9	2.5	20

[Table 119]

Mortallty (%) of single agent and mixed agent against

Haemaphysaiis longlcornls(5)

326 ’ «

Insecticide name	Compound P212
Rate pg
0	1.18
—	0	23
imidacloprid	Rate	1.9	7.7	60
dinotefuran	pg	1.9	0

[Table 120]

Theoretical value (%) by Colby's équation

Insecticide name	Compound P212
Rate pg
0	1.18
—	0	23
imidacloprid	Rate	1.9	7.7	32
dinotefuran	pg	1.9	0	25

Claims

[Claim 1]

A pest control composition, comprising:

at least one of a novel Imlnopyridine derlvatlve represented by the following Formula (I) or acid addition salts thereof as an active Ingrédient; and at least one of other pest control agents:

[Chemical Formula 1] [In the formula, Ar represents a phenyl group which may be substituted, a 5- to 6membered heterocycle which may be substituted, or a 4- to 10-membered heterocycloalkyl group,

A represents a heterocycle having a 5- to 10-membered unsaturated bond including one or more nitrogen atoms, and has an Imino group substituted with an R group at a position adjacent to the nitrogen atom présent on the cycle,

Y represents a hydrogen atom, a halogen atom, a hydroxyl group, a C1 to C6 alkyl group which may be substituted with a halogen atom, a C1 to C6 alkyloxy group which may be substituted with a halogen atom, a cyano group, or a nitro group, and

R represents any one of groups represented by the following Formulae (a) to (e), (y) or (z), [Chemical Formula 2]

—C-Rî II —c-or₂ —c-r₃ Il ^J —c-r₅ Il ³ —c-r₇ II X’ Ry η-s-Rz O 0 S N I N I -P-Y₂ ⁰ n ORe 1 (a) (b) (c) (d) (e) (y) ^Ry (z)

328 here, R1 represents a hydrogen atom, a substituted C1 to C6 alkyl group, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, or a pentafluorophenyl group,

R2 represents a C1 to C6 alkyl group which may be substituted with a halogen atom, an unsubstituted C3 to C6 branched or cycllc alkyl group, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to C10) aryl group, a substituted or unsubstituted 5- to 10-membered heterocycle, or a substituted or unsubstituted benzyl group,

R3 represents a C1 to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to C10) aryl group, a substituted or unsubstituted (C6 to C10) aryl (C1 to C6) alkyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkenyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkynyl group, a substituted or unsubstituted phenoxy (C1 to C6) alkyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkenyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkynyl group, a substituted or unsubstituted 5- to 10-membered heterocycle, a substituted or unsubstituted 5- to 10-membered heterocycle (C1 to C6) alkyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkenyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkynyl group, a (C1 to C4) alkoxy (C1 to C5) alkyl group, a (C1 to C4) alkoxy (C2 to C5) alkenyl group, a (C1 to C4) alkoxy (C2 to C5) alkynyl group, a (C1 to C4) alkylthio (C1 to C5) alkyl group, a (C1 to C4) alkylthio (C2 to C5) alkenyl group, or a (C1 to C4) alkylthio (C2 to C5) alkynyl group,

R4 represents a hydrogen atom, a formyl group, a C1 to C6 alkyl group which

329

I . l may be substituted, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to C10) aryl group, a substituted or unsubstituted (C6 to C10) aryl (C1 to C6) alkyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkenyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkynyl group, a substituted or unsubstituted phenoxy (C1 to C6) alkyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkenyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkynyl group, a substituted or unsubstituted 5- to 10-membered heterocycle, a substituted or unsubstituted 5- to 10-membered heterocycle (C1 to C6) alkyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkenyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkynyl group, a (C1 to C4) alkoxy (C1 to C5) alkyl group, a (C1 to C4) alkoxy (C2 to C5) alkenyl group, a (C1 to C4) alkoxy (C2 to C5) alkynyl group, a (C1 to C4) alkylthio (C1 to C5) alkyl group, a (C1 to C4) alkylthio (C2 to C5) alkenyl group, a (C1 to C4) alkylthio (C2 to C5) alkynyl group, or a group represented by the foliowing Formulae (f) to (n) [Chemical Formula 3] ' O ^“Ria Çf“°R4b S“R4c ⁰ m ⁰ (o) ⁰ C» —C-R<d —C-OR^ —C- SR_4d C-SR_4d

^S (i) s S ω 0 (k) (I) Rie R4e —C-N Il * —c- -N H _ o R«r . . Il (m) s R_4f (n)

here, R4a, R4b and R4c represent a C1 to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted

330 with a haiogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to C10) aryl group, a substituted or unsubstituted (C6 to C10) aryl (C1 to C6) alkyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkenyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkynyl group, a substituted or unsubstituted phenoxy (C1 to C6) alkyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkenyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkynyl group, a substituted or unsubstituted 5- to 10-membered heterocycle, a substituted or unsubstituted 5- to 10-membered heterocycle (C1 to C6) alkyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkenyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkynyl group, a (C1 to C4) alkoxy (C1 to C5) alkyl group, a (C1 to C4) alkoxy (C2 to C5) alkenyl group, a (C 1 to C4) alkoxy (C2 to C5) alkynyl group, a (C1 to C4) alkylthio (C1 to C5) alkyl group, a (C1 to C4) alkylthio (C2 to C5) alkenyl group, or a (C1 to C4) alkylthio (C2 to C5) alkynyl group,

R4d represents a C1 to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to C10) aryl group, or a substituted or unsubstituted 5- to 10membered heterocycle, and

R4e and R4f each independently represent a hydrogen atom, a C1 to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to C10) aryl group, or a substituted or unsubstituted 5- to 10-membered heterocycle),

R5 represents a C1 to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a haiogen atom, a C2 to

331 il-; o Viîi'î/Ί i

C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to C10) aryl group, a substituted or unsubstituted (C6 to C10) aryl (C1 to C6) alkyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkenyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkynyl group, a substituted or unsubstituted phenoxy (C1 to C6) alkyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkenyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkynyl group, a substituted or unsubstituted 5- to 10-membered heterocycle, a substituted or unsubstituted 5- to 10-membered heterocycle (C1 to C6) alkyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkenyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkynyl group, a (C1 to C4) alkoxy (C1 to C5) alkyl group, a (C1 to C4) alkoxy (C2 to C5) alkenyl group, a (C1 to C4) alkoxy (C2 to C5) alkynyl group, a (C1 to C4) alkytthio (C1 to C5) alkyl group, a (C1 to C4) alkylthio (C2 to C5) alkenyl group, or a (C1 to C4) alkytthio (C2 to C5) alkynyl group,

R6 represents a hydrogen atom, a formyl group, a O,O*-C1 to C4 alkyl phosphoryl group, a C1 to C18 alkyl group which may be substituted, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to C10) aryl group, a substituted or unsubstituted (C6 to C10) aryl (C1 to C6) alkyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkenyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkynyl group, a substituted or unsubstituted phenoxy (C1 to C6) alkyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkenyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkynyl group, a substituted or unsubstituted 5- to 10-membered heterocycle, a substituted or unsubstituted 5- to 10-membered heterocycle (C1 to C6) alkyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkenyl group, a substituted or i u 0ΛΌ7 l.l?n i

332 unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkynyl group, a (C1 to C4) alkoxy (C1 to C5) alkyl group, a (C1 to C4) alkoxy (C2 to C5) alkenyl group, a (C1 to C4) alkoxy (C2 to C5) alkynyl group, a (C1 to C4) alkylthio (C1 to C5) alkyl group, a (C1 to C4) alkylthio (C2 to C5) alkenyl group, a (C1 to C4) alkylthio (C2 to C5) alkynyl group, or a group represented by the following Formulae (o) to (x) [Chemical Formula 4] —C-Re, Ô (o) —C-ORet ô (P)

O

-^-Rec (q) —C-Rea «

- C-ORed fi (s) —Ç-SR_m -C-SR_BdS O (t) (u) —C-lsi

Π ' O

Rs· ker (v) (w)

R« —Si-R_BJ

Rak (x) here, R6a, R6b and R6c represent a C1 to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to C10) aryl group, a substituted or unsubstituted (C6 to C10) aryl (C1 to C6) alkyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkenyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkynyl group, a substituted or unsubstituted phenoxy (C1 to C6) alkyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkenyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkynyl group, a substituted or unsubstituted 5- to 10-membered heterocycle, a substituted or unsubstituted 5- to 10-membered heterocycle (C1 to C6) alkyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkenyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkynyl group, a (C1 to C4) alkoxy (C1 to C5) alkyl group, a (C1

333 to C4) alkoxy (C2 to C5) alkenyl group, a (C1 to C4) alkoxy (C2 to C5) alkynyl group, a (C1 to C4) alkylthio (C1 to C5) alkyl group, a (C1 to C4) alkylthio (C2 to C5) alkenyl group, or a (C1 to C4) alkylthio (C2 to C5) alkynyl group,

R6d represents a C1 to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to C10) aryl group, or a substituted or unsubstituted 5- to 10membered heterocycle,

R6e and R6f each independently represent a hydrogen atom, a C1 to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a (C1 to C4) alkoxy (C1 to C5) alkyl group, a (C1 to C4) alkylthio (C1 to C5) alkyl group, a substituted or unsubstituted (C6 to C10) aryl group, a substituted or unsubstituted (C6 to C10) aryl (C1 to C6) alkyl group, or a substituted or unsubstituted 5-to 10-membered heterocycle,

R6g and R6h each Independently represent a hydrogen atom, a C1 to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to C10) aryl group, or a substituted or unsubstituted 5- to 10-membered heterocycle, and

R6i, R6j and R6k each independently represent a hydrogen atom, a C1 to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, or a substituted or unsubstituted (C6 to C10) aryl group), and

R7 represents a C1 to C6 alkyl group which may be substituted with

334 a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to C10) aryl group, a substituted or unsubstituted (C6 to C10) aryl (C1 to C6) alkyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkenyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkynyl group, a substituted or unsubstituted phenoxy (C1 to C6) alkyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkenyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkynyl group, a substituted or unsubstituted 5- to 10-membered heterocycle, a substituted or unsubstituted 5- to 10-membered heterocycle (C1 to C6) alkyl group, a substituted or unsubstituted 5* to 10-membered heterocycle (C2 to C6) alkenyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkynyl group, a (C1 to C4) alkoxy (C1 to C5) alkyl group, a (C1 to C4) alkoxy (C2 to C5) alkenyl group, a (C1 to C4) alkoxy (C2 to C5) alkynyl group, a (C1 to C4) alkylthio (C1 to C5) alkyl group, a (C1 to C4) alkylthio (C2 to C5) alkenyl group, or a (C1 to C4) alkylthio (C2 to C5) alkynyl group,

Y1 and Y2 represent an oxygen atom or a sulfur atom, and may be the same or different, and

Ry represents a C1 to C6 alkyi group which may be substituted with a haiogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to C10) aryl group, a substituted or unsubstituted (C6 to C10) aryl (C1 to C6) alkyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkenyl group, a

335 substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkynyl group, a substituted or unsubstituted phenoxy (C1 to C6) alkyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkenyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkynyl group, a substituted or unsubstituted 5- to 10-membered heterocycle, a substituted or unsubstituted 5- to 10-membered heterocycle (C1 to C6) alkyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkenyl group, or a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkynyl group,

Rz represents a C1 to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to C10) aryl group, a substituted or unsubstituted (C6 to C10) aryl (C1 to C6) alkyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkenyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkynyl group, a substituted or unsubstituted phenoxy (C1 to C6) alkyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkenyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkynyl group, a substituted or unsubstituted 5- to 10-membered heterocycle, a substituted or unsubstituted 5- to 10-membered heterocycle (C1 to C6) alkyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkenyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkynyl group, a (C1 to C4) alkoxy (C1 to C5) alkyl group, a (C1 to C4) alkoxy (C2 to C5) alkenyl group, a (C1 to C4) alkoxy (C2 to C5) alkynyl group, a (C1 to C4) alkylthio (C1 to C5) alkyl group, a

336

1' ! t¹ ' ' 1 (C1 to C4) alkylthlo (C2 to C5) alkenyl group, or a (C1 to C4) alkylthio (C2 to C5) alkynyl group, and n represents 1 or 2], [Claim 2]

A pest control composition acoording to claim 1, comprising:

at least one of an amine derlvative represented by the following

Formula (la) or acid addition salts thereof as an active Ingrédient; and at least one of other pest control agents:

[Chemical Formula 5]

Ri (la) [here, Ar represents a pyridyl group which may be substituted with a halogen atom, a hydroxyl group, a C1 to C6 alkyl group which may be substituted with a halogen atom, a C1 to C6 alkyloxy group which may be substituted with a halogen atom, a cyano group, or a nitro group, or a pyrimldyl group which may be substituted with a halogen atom, a C1 to C4 alkyl group which may be substituted with a halogen atom, an alkyloxy group which may be substituted with a halogen atom, a hydroxyl group, a cyano group, or a nitro group,

Y represents a hydrogen atom, a halogen atom, a hydroxyl group, a C1 to C6 alkyl group which may be substituted with a halogen atom, a C1 to C6 alkyloxy group which may be substituted with a halogen atom, a cyano group, or a nitro group, and

337 v | ’ »0 '

R1 represents a C1 to C6 alkyl group which Is substituted with halogen].

[Claim 3]

The pest control composition according to claim 1, wherein Ar Is a 6chloro-3-pyridyl group, a 6-chloro-5-fluoro-3-pyridyl group, a 6-fluoro-3pyridyl group, a 6-bromo-3-pyridyl group and a 2-chloro-5-pyrimidyi group. [Claim 4]

The pest control composition according to daims 1 or 3, wherein in Formula (I), A Is the following Formula (A-1):

[Chemical Formula 6] (A-1) and Y is a hydrogen atom, a halogen atom and a cyano group. [Claim 5]

The pest control composition according to daims 1, 3 or 4, wherein R in Formula (I) Is a group with Formula (c).

[Chemical Formula 7] —c-r₃ ii ^J

S (c) [Claim 6]

The pest control composition according to daims 1, 3 or 4, whereln R in Formula (I) is a group with Formula (a).

[Chemical Formula 8]

338 —C-Ri

Il ¹

O (a) [Claim 7]

The pest control composition according to clalms 1, 3 or 4, wherein

R ln Formula (1) is a group with Formula (d) [[Chemical Formula 9] —c-r₅ ii ⁰

N i

R4 (d) and R4 is a C1 to C18 alkyl group which may be substituted, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to C10) aryl group, a substituted or unsubstituted (C6 to C10) aryl (C1 to C6) alkyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkenyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkynyl group, a substituted or

unsubstituted phenoxy (C1 to C6) alkyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkenyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkynyl group, a substituted or unsubstituted 5- to 10-membered heterocycle, a substituted or

unsubstituted 5- to 10-membered heterocycle (C1 to C6) alkyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkenyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkynyl group, a (C1 to C4) alkoxy (C1 to C5) alkyl

339 •'^ri: <

group, a (C1 to C4) alkoxy (C2 to C5) alkenyl group, a (C1 to C4) alkoxy (C2 to C5) alkynyl group, a (C1 to C4) alkylthio (C1 to C5) alkyl group, a (C1 to C4) alkylthio (C2 to C5) alkenyl group, a (Cl to C4) alkylthio (C2 to C5) alkynyl group, and R5 is a C1 to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, and R5 Is a C1 to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom.

[Claim 8]

The pest control composition according to claim 1, wherein the Imlnopyrldlne derivatlve is N-[1’((6-chloropyr1dln-3-yl)methyl)pyridln2(1H)-ylldene]-2,2,2-trlfluoroacetamlde or N-[1-((6-chloropyridin-3y1)methy1)pyr1dln-2(1H)-ylldene]-2,2,2-trlfluoroethanethioamlde, or N-[1((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylldene]-2,2,2-trlfluoro-N'Isopropylacetlmidamide.

[Claim 9]

The pest control composition according to clalms 1 to 8, further comprising an agrlculturally and zootechnlcally acceptable carrier. [Claim 10]

The pest control composition according to daims 1 to 8, wherein the other pest control agents are an Insecticide and/or a funglclde.

[Claim 11]

The pest control composition according to clalms 1 to 8, wherein the other pest control agents are an insecticide.

340 _k , l I V*¹ [Claim 12]

The pest control composition according to claims 1 to 9, wherein the other pest control agents are, as an insecticide, an insecticide selected from the group consisting of an organic phosphoric ester compound including acephate, dichlorvos, EPN, fenltrothion, fenamifos, prothlofos, profenofos, pyraclofos, chlorpyrifos-methyl, diazinon, trichlorfon, tetrachlorvinphos, bromofenofos and cythioate, a carbamate-based compound including methomyl, thlodicarb, aldicarb, oxamyl, propoxur, carbaryl, fenobucarb, ethlofencarb, fenothiocarb, plrimicarb, carbofuran and benfuracarb, a nereistoxin dérivative including cartap and thlocyciam, an organochlorine compound including dicofol and tetradifon, a pyrethroidbased compound Including allethrin, dd-T allethrin, dl-d-T80 allethrin, pyrethrins, phenothrin, flumethrin, cyfluthrin, d-d-T80 prarethrin, phthalthrin, transfluthrin, resmethrin, cyphenothrin, pyrethrum extract, synepirin 222, syneplrin 500, permethrin, tefluthrln, cypermethrln, deltamethrin, cyhalothrln, fenvalerate, fluvalinate, ethofenprox and sllafluofen, a benzoyl urea-based compound Including dlflubenzuron, teflubenzuron, flufenoxuron, chlorfluazuron and lufenuron, a juvénile hormone-like compound including methoprene, a molting hormone-like compound Including chromafenozide, buprofezln, hexythiazox, amitraz, chlordimeform, pyridaben, fenpyroxymate, pyrimidifen, tebufenpyrad, tolfenpyrad, acequlnocyl, cyflumetofen, flubendizmide, ethiprole, fipronil, etoxazole, imldacloprld, clothlanidin, thiamethoxam, acetamiprid, nitenpyram, thlacloprid, dlnotefuran, pymetrozine, blfenazate, spirodiclofen, spiromesifen, splrotetramat, flonicamid, chlorfenapyr, pyriproxyfen, indoxacarb, pyridaiyl, splnosad, spinetoram, avermectin, milbemycin, pyflubumide, cyenopyrafen, pyrifluqulnazon, chlorantraniliprole, cyantraniliprole, lepimectin, metaflumlzone, pyrafluprole, pyriprole, hydramethylnon, triazamate, sulfoxaflor, flupyradifurone, flometoquin, ivermectln, selamectin, moxldectin, doramectin,

341 eprinomectin, milbemycin oxim, deet, metoxadlazon, cyromazine, triflumuron, star anise oil, triciabendazole, flubendazole, fenbendazole, antimony sodium gluconate, leva mi sole hydrochloride, bithionol, dichlorofen, phenothiazine, plperazine carbon bisulfide, plperazine phosphate, plperazine adipate, piperazine citrate, melarsomine dihydrochloride, metyridine, santonin, pyrantel pamoate, pyrantel, praziquantel, febantel, emodepside, emamectin benzoate, cycloxaprid, 1-((6-chloropyridin-3yl)methyl)-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimidin-1-ium-2-olate, an organic metalbased compound, a dinitro-based compound, an organic sulfur compound, a ureabased compound, a triazîne-based compound, a hydrazine-based compound, and a compound represented by the following Formula (II) or an agriculturally and zootechnically acceptable acid addition sait thereof:

[Chemical Formula 10] (H) [in the formula,

Het1 represents a 3-pyridyl group,

R1 represents a hydroxyl group,

R2 and R3 represent a cyciopropylcarbonyloxy group, and

R4 represents a hydroxyl group].

[Claim 13]

The pest control composition according to claims 1 to 9, wherein the other pest

342 !* \ .'I i '> control agents are, as a fungicide, a fungicide selected from the group consisting of a strobilurin-based compound Including azoxystrobln, orysastrobin, kresoxym-methyl and trifloxystrobin, an aniiinopyrimidine-based compound including mepanipyrim, pyrimethanil and cyprodtnil, an azoie-based compound including triadîmefon, bltertanol, triflumizole, etaconazole, proplconazole, penconazole, flusiiazole, myclobutanil, cyproconazole, tebuconazole, hexaconazole, prochloraz and simeconazole, a quinoxaline-based compound including quinomethionate, a dithiocarbamate-based compound Including maneb, zineb, mancozeb, poiycarbamate and propineb, a phenyl carbamate-based compound Including diethofencarb, an organochlorine compound including chlorothalonil and quintozene, a benzimldazoie-based compound Including benomyl, thiophanate-methyl and carbendazole. a phenyl amide-based compound Including metalaxyl, oxadixyl, ofurase, benalaxyl, furalaxyl and cyprofuram, a sulfenic acld-based compound including dichiofluanid, a copper-based compound including copper hydroxide and oxine-copper, an isoxazole-based compound including hydroxyisoxazole, an organic phosphorus-based compound Including fosetyl-aiuminlum and toiclofos-methyl, an Nhaiogenothioalkyl-based compound including captan, captafot and folpet, a dicarboximide-based compound Including procymidone, iprodione and vinchlozolin, a benzanllide-based compound Including thifluzamlde, furametpyr, flutolanil and mepronil, a morpholine-based compound including fenproplmorph and dimethomorph, an organic tin-based compound including fenthln hydroxide and fenthin acetate, a cyanopyrrolebased compound Including fludioxonil and fenpiclonii, acïbenzoiar-S-methyl, isotianii, tiadinii, carpropamld, diclocymet, fenoxanil, tricydazole, pyroquilon, ferimzone, fthaiide, fluazinam, cymoxanii, triforine, pyrifenox, probenazole, fenarimol, fenpropidin, pencycuron, cyazofamld, Iprovallcarb, tebufloquln, benthiavaiicarb-isopropyl, tolprocarb, validamycln, Kasugamycin, Streptomycln, a 9-membered cyciic dilactone compound

343 including UK-2As, a compound represented by the following Formula (III), a compound represented by the following Formula (IV), and a compound represented by the following Formula (V), or agriculturally and zootechnlcally acceptable acid addition salts thereof.

[Chemical Formula 11] (m) [in the formula, R1 and R2 represent a hydrogen atom or a haloalkyl group having 1 to 6 carbon atoms (with the proviso that at least one of R1 and R2 represents a haloalkyl group having 1 to 6 carbon atoms), R3 represents a hydrogen atom, A represents OR4, SRS, NR6R7 or NR8NR9R10, R4 represents an alkyl group having 8 to 12 carbon atoms, R5 represents an alkyl group having 1 to 12 carbon atoms, R6 and R7 represent a hydrogen atom or an alkyl group having 8 to 12 carbon atoms, and R8, R9 and R10 represent a hydrogen atom or an alkyl group having 1 to 12 carbon atoms] [Chemical Formula 12] [ ln the formula, R1 and R2 represent a C1 to C6 alkyl group, an aryl group, a heteroaryl group, or a aralkyl group,

R3 and R4 represent a hydrogen atom, a C1 to C6 alkyl group, a halogen atom, or a C1 to C6 alkoxy group,

X represents a hydrogen atom, a halogen atom, a C1 to C6 alkyl group,

344 ι’\ί>1 1170/0 V«O | 120 1 a C2 to C6 alkenyl group, a C2 to C6 alkynyl group, an aryl group, a heteroaryl group, or a C1 to C6 alkoxy group,

Y represents a hydrogen atom, a halogen atom, a C1 to C6 alkyl group, or a C1 to C6 alkoxy group, n represents 0 to 4, and m represents 0 to 6 ] [Chemical Formula 13] [In the formula, R1 represents an alkyl group, R2 and R3 each Independently represent a hydrogen atom and a haloalkyl group (with the proviso that at least one of R2 and R3 Is a haloalkyl group having 1 to 6 carbon atoms), A represents -OR4, -SR5, -NR6R7 or -NR8NR9R10, R4 represents an alkyl group having 3 to 12 carbon atoms, R5 represents an alkyl group having 1 to 12 carbon atoms, R6 represents a hydrogen atom, R7 represents an alkyl group having 5 to 12 carbon atoms, and R8, R9 and R10 each represent an alkyl group having 1 to 12 carbon atoms, respectively].

[Claim 14]

The pest control composition according to claims 1 to 9, wherein the other pest control agents are, as an insecticide, an Insecticide selected from the group consisting of permethrin, Imidacloprid, clothlanidin, dinotefuran, thlacloprid, thiamethoxam, pymetrozlne, splnosad, spinetoram, fipronil, chloranthranlliprole, cyantraniliprole, ethofenprox, silafluofen, amitraz, ethiprole, flonicamid, sulfoxaflor, flupyradifurone, flometoquin, Ivermectin, moxidecyin, emamectin benzoate, cycloxaprid, 1-((6-chloropyridin-3-yl)methyl)-4-oxo-3-phenyl-4H-pyrido[1,2345

a]pyrimtdîn-1-ium-2-olate and afidopyropen, or an agriculturally and zootechnically acceptable acid addition sait thereof.

[Claim 15]

The pest control composition according to claims 1 to 9, wherein the other pest control agents are, as a fungicide, a fungicide selected from the group consisting of azoxystrobln, orysastrobln, thifluzamlde, furametpyr, fthalide, probenazole, acibenzolar-S-methyl, tladinil, Isotianil, carpropamid, diclocymet, fenoxanil, tricyclazole, pyroquilon, ferimzone, tebufloquin, simeconazole, validamycin, kasugamycln and pencycuron.

[Claim 16]

A combined product comprising:

an imlnopyridine dérivative which ls N-[1-((6-chloropyrldln-3yi)methyl)pyridin-2(1 H)-ylidene]-2,2,2-trifluoroacetamide or acid addition salts thereof, N-[ 1 -((6-chloropyridin-3-yl)methyl)pyrldin-2( 1 H)-ylidene]2,2,2-trifiuoroethanethloamlde or acid addition salts thereof or N-[1-((6chloropyridin-3-yi)methyl)pyrldln-2(1H)-ylidene]-2,2,2-trifluoro-N'isopropylacetimidamide or acid addition salts thereof; and at least one of other pest control agents.

[Claim 17]

A method for protectlng useful plants or animais from pests, comprising:

simultaneously or Independently applying an imlnopyridine dérivative which is N-[1-((6-chloropyrldln-3-yl)methyi)pyridin-2(1H)ylidene]-2,2,2-trifluoroacetamide or acid addition salts thereof, N-[1-((6chloropyridln-3-yl)methyl)pyridin-2( 1 H)-ylldene]-2,2₁2trifiuoroethanethioamide or acid addition salts thereof, or N-[1-((6346 chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoro-N'Isopropylacetimldamide or acid addition salts thereof; and at least one of other pest control agents to a région to be treated.

[Claim 18]

5 A method for protecting useful plants or animais from pests by treating pests, useful plants, seeds of useful plants, soil, cultivation carriers or animais as a target, with an effective amount of the pest control composition of daims 1 to 15.

[Claim 19]

10 A method for protecting useful plants or animais from pests by applying the combined product of claim 16 to pests, useful plants, seeds of useful plants, soil, cultivation carriers or animais as a target. [Claim 20]

A use of the pest control composition according to daims 1 to 15 for

15 protecting useful plants from pests.

[Claim 21]

A use of the combined product according to claim 16 for protecting useful plants from pests.

[Claim 22]

20 The composition according to daims 1 to 8, wherein the other pest control agents are a control agent for animai parasitic pests.

[Claim 23]

The composition according to claim 22, wherein the other pest control agents are a control agent for animal parasitic pests selected from 25 the group consisting of an organophosphate ester compound including dlchlorvos, EPN, fenitrothlon, fenamifos, prothlofos, profenofos,

347 rx-.nritο i pyraclofos, chlorpyrifos-methyl, dlazlnon, trichlorfon, tetrachiorvinphos, bromofenofos, cythioate, and fenthion; a carbamate-based compound Including methomyl, thlodicarb, aldlcarb, oxamyl, propoxur, carbaryl, fenobucarb, ethlofencarb, fenothiocarb, plrimlcarb, carbofuran, and benfuracarb; a nereistoxin dérivative Including cartap and thiocyclam; an organochlorlne compound Including dicofol and tetradlfon; a pyrethroidbased compound Including allethrln, d d-T allethrin, dl-d-T80 aliethrin, pyrethrlns, phenothrln, fiumethrin, cyfluthrln, d-d-T80 prarathrln, phthalthrin, transfluthrln, resmethrin, cyphenothrin, pyrethrum extract, syneplrln 222, synepirin 500, permethrin, tefluthrin, cypermethrln, deltamethrin, cyhaiothrin, fenvaierate, fiuvaiinate, ethofenprox, and sllafluofen; a benzoyl urea-based compound Including dlflubenzuron, teflubenzuron, flufenoxuron, chlorfiuazuron, and lufenuron; a juvénile hormone-like compound including methoprene; a moiting hormone-like compound Including chromafenozlde; and amltraz, chiordimeform, fîpronil, etoxazole,

Imidacloprid, clothianldin, thiamethoxam, acetamiprld, nitenpyram, thiacloprid, dinotefuran, spirodiclofen, pyriproxyfen, indoxacarb, spinosad, spinetoram, avermectln, milbemycin, metaflumlzone, pyrafluprole, pyriprole, hydramethylnon, triazamate, sulfoxaflor, fiupyradifurone, ivermectin, selamectin, moxidectin, doramectin, eprinomectin, milbemycin oxlm, diethylcarbamazlne citrate, deet, metoxadiazon, cyromazine, triflumuron, star anise oil, triclabendazole, fiubendazole, fenbendazole, antimony sodium gluconate.

levamisole hydrochloride, bithionol, dlchlorofen, phenothiazine, piperazine carbon bisulfide, piperazine phosphate, piperazine adipate, piperazine citrate, melarsomine dlhydrochloride, metyridine, santonin,

348 pyrantel pamoate, pyrantel, praziquantel, febantel, emodepslde, derquantel, monopantel, emamectin benzoate, cycloxaprld, or an agrlculturally and zootechnlcally acceptable acid addition sait thereof. [Claim 24]

5 The composition according to claim 22 or 23, wherein the other pest control agents are a control agent for animal parasitic pests selected from the group consisting of fiumethrln, permethrln, fipronil, pyriprol, Imidacloprid, thiamethoxam, acetamlprld, dinotefuran, amltraz, metaflumlzon, pyriproxyfen, fenltrothlon, lufenuron, ethoxazol, spinosad, 10 spinetoram, emodepslde, emamectin benzoate, Ivermectin, selamectin, moxidectin, doramectin, eprinomectin, praziquantel, derquantel, monopantel, or an agrlculturally and zootechnlcally acceptable acid addition sait thereof.

[Claim 25]

15 A comblned product comprising:

an Imlnopyrldlne derlvatlve which Is N-[1-((6-chloropyridin-3yl)methyl)pyrldin-2(1H)-ylidene]-2,2,2-trifluoroacetamlde or an acid addition sait thereof, N-[1-((6-chloropyridln-3-yl)methyl)pyridin-2(1H)ylldene]-2,2,2-trifluoroethanethloamide or an acid addition sait thereof, or 20 N-[1-((6-chloropyrldln-3-yl)methyl)pyridln-2(1H)-ylidene]-2,2,2-trlfluoroN'-lsopropylacetlmidamlde or an addition sait thereof; and at least one of other control agents for animal parasitic pests.

[Claim 26]

A method for protecting animais from pests, comprising:

25 simuitaneously or Independently applylng, to a région to be treated, an Imlnopyrldlne derlvatlve which Is N-[1-((6-chloropyridin-3349

11 ; t¹ ' ⁽ » yl)methyl)pyridln-2(1 H)-ylidene]-2,2,2-trifluoroacetamide or an acid addition sait thereof, N-[1-((6-chloropyridln-3-yl)methyl)pyrldin-2(1H)ylldene]-2,2,2-trlfluoroethanethloamide or an acid addition sait thereof, or N-[1-((6-chloropyrldln-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trlfluoro5 N’-lsopropylacetlmidamide or an addition sait thereof; and at least one of other control agents for animal parasitic pests.

[Claim 27]

A use of the pest control composition according to clalms 1 to 15 and 22 to 24 for protecting animais from pests.

10 [Claim 28]

A use of the combined product according to claim 25 for protecting animais from pests.