JPH0827118A - Imidazolinone derivative - Google Patents

Abstract

PURPOSE:To obtain a new imidazolinone derivative having excellent insecticidal and acaricidal activities against various kinds of agricultural harmful insects and spider mites, almost free from harmful effects against mammals, fishes and beneficial insects and useful as pest controlling agent. CONSTITUTION:This is a compound of formula I [R<1> is H, a 1-6C (halo)alkyl, a 3-6C cycloalkyl, formyl, a 2-6C alkylcarbonyl, a 2-6C cyanoalkyl, benzyl, phenyl, CN, NH2, SR<10> (R<10> is a 2-6C alkoxycarbonyl, etc.), an alkali metal, etc.; R<2> is H, a 1-6C (halo)alkyl, a 2-6C alkenyl, (substituted) phenyl, etc.; X is a halogen, a 1-4C alkyl, a 1-4C alkoxy, CN, etc.; l=1-5; Y is a halogen, a 1-6C (halo)al-kyl, a 1-4C alkoxy, CN, etc.; m=1-5; Z is O, S or NH], e.g. 2-(2-chloro-6-fluorophenyl)-5-(4-chlorophenyl)-5-methyl-4-(5H)-imidazo linone. A compound which is expressed by formula I and has H as the R<1> is obtained by reacting a compound of formula II with a base in an inert solvent.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a novel imidazolinone derivative and a pest control agent containing the derivative as an active ingredient.

[0002]

2. Description of the Related Art Heretofore, some patents and literatures have described imidazolinone derivatives. Tetrahedron, 40, 2395 (1
984) and Pharmaceutical Journal, 97, 223 (1977).
Describes 4 (5H) -imidazolinone having a phenyl group at the 2- and 5-positions, but the above literature does not show any activity as a pest control agent.

Further, German Patent DE 3408403 describes 2,5-diphenyl-4 (5H) -imidazolinone having herbicidal activity, but the phenyl group at the 5-position is substituted only in the present invention. The phenyl group is not mentioned. Furthermore, no insecticidal and acaricidal activity has been shown.

[0004]

Due to the long-term use of insecticides, pests have acquired resistance in recent years, making it difficult to control them with conventional insecticides. In addition, some insecticides are highly toxic, and some are perturbing the ecosystem due to persistence. Therefore, the development of new insecticides with low toxicity and low residue is always expected.

The present inventors have conducted extensive studies on imidazolinone derivatives, and as a result, novel 2,5-diphenyl-
The present invention has been completed by finding that the 4 (5H) imidazolinone derivative is a very useful compound which exhibits excellent insecticidal activity at a low dose and has little adverse effect on mammals, fish and beneficial insects.

[0006]

The present invention has the general formula (I)

[0007]

[Chemical 4]

[In the formula, R ¹ is a hydrogen atom, a C _{1 to} C ₆ alkyl group, a C _{3 to} C ₆ cycloalkyl group, a C _{2 to} C ₆ alkenyl group, and a C ₂
-C ₆ alkynyl group, C ₁ -C ₆ haloalkyl group, C ₂ -C ₆ alkoxyalkyl group, formyl group, C ₂ -C ₆ alkylcarbonyl group, C ₂ -C ₆ alkoxycarbonyl group, C ₃ -C ₆ alkoxy carbonyl alkyl group, C ₂ -C ₆ cyanoalkyl radical,
Benzyl group, a phenyl group, a cyano group, an amino group, C ₃ -C ₆
Alkoxycarbonylcarbonyl group, -SR ¹⁰ group (wherein R ¹⁰ is a C _{2 to} C ₆ alkoxycarbonyl group, C _{1 to} C ₆ alkylsulfonyl group, -NR ¹¹ R ¹² group (wherein R ¹¹ is C _{1 to} C ₆
Represents an alkyl group, R ¹² is a C _{1 to} C ₆ alkyl group, a C _{2 to} C ₆ alkoxycarbonyl group, a C _{3 to} C ₉ alkoxycarbonylalkyl group, a C _{1 to} C ₆ alkylsulfonyl group, C _{2 to} C ₆ alkyl A carbonyl group, a C _{3 to} C ₉ dialkylaminocarbonyl group, a C _{2 to} C ₆ dialkylaminosulfonyl group or an unsubstituted or optionally substituted phenyl group), or an unsubstituted or optionally substituted phenyl group (However, as the substituent which may be substituted, a halogen atom, a cyano group, a nitro group, a C _{1 to} C ₄ alkyl group, a C _{1 to} C ₄ haloalkyl group, a C _{1 to} C ₄ alkoxy group, and a C _{1 to} C group. ₄ haloalkoxy group, C _{1 to} C ₄ alkylthio group, C _{1 to} C ₄ haloalkylthio group, C _{2 to} C ₆ alkoxycarbonyl group, C _{2 to} C ₆ haloalkoxycarbonyl group, C _{2 to} C ₆ alkylcarbonyl group, C ₂
~ C ₆ haloalkylcarbonyl group, C ₁ ~ C ₄ alkylsulfonyl group or C ₁ ~ C ₄ haloalkylsulfonyl group,
When the number of the substituents is two or more, the substituents may be the same or different. }, An alkali metal or an alkaline earth metal, wherein R ² is a hydrogen atom, a C ₁ -C ₆ alkyl group, a C ₃ -C ₆ cycloalkyl group, a C ₂ -C ₆ alkenyl group, C ₂
To C ₆ alkynyl group, C _{5 to} C ₆ cycloalkenyl group, C _{1 to} C ₆
Haloalkyl groups, C ₂ -C ₆ alkoxyalkyl group, C ₃ -C ₆
Halocycloalkyl group, C ₂ -C ₆ haloalkenyl group, C ₂ ~
C ₆ haloalkynyl group, or an unsubstituted or optionally substituted phenyl group (provided that the optionally substituted substituent is a halogen atom, a C _{1 to} C ₄ alkyl group, a C ₁ to
C ₄ haloalkyl group, C _{1 to} C ₄ alkoxy group, C _{1 to} C ₄ haloalkoxy group, C _{1 to} C ₄ alkylthio group or C _{1 to} C ₄ haloalkylthio group, and when two or more substituents are present, The substituents may be the same or different), X is a halogen atom, a C ₁ -C ₄ alkyl group, a C ₁ -C ₄ alkoxy group,
C ₁ -C ₄ alkylthio group, C ₁ -C ₄ haloalkyl groups, C ₁ -C ₄
A haloalkoxy group, a C ₁ -C ₄ haloalkylthio group, an amino group, a cyano group, or a nitro group, 1 is an integer of 1 to 5 (provided that in the case of 2 to 5, X may be the same or different) Y) is a halogen atom, a C _{1 to} C ₆ alkyl group, a C _{2 to} C ₆ alkenyl group, a C _{2 to} C ₆ alkynyl group, a C ₃
To C ₆ cycloalkyl group, C _{1 to} C ₆ haloalkyl group, C _{2 to} C ₆
Haloalkenyl group, C ₂ -C ₆ haloalkynyl group, C ₃ -C ₆ halocycloalkyl group, C ₂ -C ₆ cyanoalkyl group, C ₁ -C ₆
Hydroxyalkyl group, C ₂ -C ₆ carboxyalkyl group,
C ₁ -C ₆ alkoxy group, C ₂ -C ₆ alkenyloxy group, C ₂ ~
C ₆ alkynyloxy group, C ₃ -C ₆ cycloalkyl group, C ₁ -C ₆ haloalkoxy group, C ₂ -C ₆ haloalkenyloxy group, C ₂ -C ₆ haloalkynyl group, C ₃ -C ₆ halo cycloalkoxy group, C ₄ -C ₇ halocycloalkyl alkoxy group, C ₁ -C ₆ alkylthio group, C ₂ -C ₆ alkenylthio group, C ₂ -C ₆ alkynylthio, C ₃ -C ₆ cycloalkylthio group , C _{1 to} C ₆ haloalkylthio group, C _{1 to} C ₆ alkylsulfinyl group, C _{2 to} C ₆ alkenylsulfinyl group, C _{2 to} C ₆
Alkynylsulfinyl group, C ₃ -C ₆ cycloalkyl alkylsulfinyl group, C ₁ -C ₆ haloalkylsulfinyl group, C ₁ ~
C ₆ alkylsulfonyl group, C ₂ -C ₆ alkenylsulfonyl group, C ₂ -C ₆ alkynylsulfonyl group, C ₃ -C ₆ cycloalkylsulfonyl group, C ₁ -C ₆ haloalkylsulfonyl group,
C ₂ -C ₆ alkoxyalkyl group, C ₂ -C ₆ alkoxyalkoxy, C ₂ -C ₆ haloalkoxyalkyl group, C ₂ -C ₆ haloalkoxy alkoxy group, C ₂ -C ₆ alkylthioalkyl group, C ₂ ~ C ₆ alkylthioalkoxy group, C ₃ -C ₆ alkoxycarbonylalkyl group, C ₃ -C ₆ alkylcarbonyl group, C ₂ -C ₆ alkoxycarbonyloxy group, C ₂ ~
C ₆ alkylcarbonyloxy group, C ₂ -C ₆ alkylcarbonyl group, C ₃ -C ₆ alkenylcarbonyl group, C ₃ -C ₆ alkynyl group, C ₄ -C ₇ cycloalkylcarbonyl group, C ₂ -C ₆ haloalkyl carbonyl group, C ₂ -C ₆ alkoxycarbonyl group, C ₂ -C ₆ haloalkoxycarbonyl groups,
C ₃ -C ₆ alkoxycarbonylalkoxy group, a nitro group,
Cyano group, hydroxy group, carboxyl group, thiocyanate group, isothiocyanate group, C ₂ -C ₆ thiocyanate alkyl group, C ₁ -C ₆ alkylsulfonyloxy group, C ₂ ~
C ₆ alkylthiocarbonyl group, amino group (-NR ³ R ⁴ ), aminocarbonyl group (-CONR ³ R ⁴ ), aminocarbonyloxy group
(-OCONR ³ R ⁴ ), amide group (-NR ³ COR ⁴ ), alkoxycarbonylamino group (-NR ³ CO ₂ R ⁴ ), aminosulfonyl group (-SO ₂ N
R ³ R ⁴ ), thioamide group (-NR ³ CSR ⁴ ), methylenedioxy group, halomethylenedioxy group, ethylenedioxy group, haloethylenedioxy group, trimethylsilyl group or

[0009]

Embedded image

{However, W is

[0011]

[Chemical 6]

(Wherein R ³ and R ⁴ are each independently a hydrogen atom, a C _{1 to} C ₆ alkyl group, a C _{2 to} C ₆ alkenyl group, a C _{2 to} C ₆
Alkynyl group, C ₁ -C ₆ haloalkyl group, C ₂ -C ₆ haloalkenyl group, C ₂ -C ₆ haloalkynyl group, C ₂ -C ₆ alkylcarbonyl group, C ₂ -C ₆ alkoxycarbonyl group, a phenyl group or A benzyl group, R ⁵ and R ⁶ each independently represent a hydrogen atom, a halogen atom, a C ₁ -C ₆ alkyl group, a C ₃ -C ₆ cycloalkyl group, a cyano group or a phenyl group, and q
Represents an integer of 0 to 2. ), N is an integer of 0 or 1, Ar is an unsubstituted or optionally substituted phenyl group, naphthyl group, furyl group, thienyl group, pyrrolyl group, pyrazolyl group, imidazolyl group, thiazolyl group, isothiazolyl Group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, triazolyl group, pyridyl group, pyridazyl group, pyrimidyl group, pyrazyl group, quinolyl group or quinoxalyl group (however,
As the substituent which may be substituted, a halogen atom, a cyano group, a nitro group, a C _{1 to} C ₄ alkyl group, a C _{1 to} C ₄ haloalkyl group, a C _{1 to} C ₄ alkoxy group, and a C _{1 to} C ₄ haloalkoxy group. , C _{1 to} C ₄ alkylthio group, C _{1 to} C ₄ haloalkylthio group, C _{1 to} C ₄ alkylsulfonyl group, C _{1 to} C ₄ haloalkylsulfonyl group, C _{2 to} C ₄ alkoxycarbonyl group, carboxyl group, amino group , Mono C ₁ -C ₄ alkylamino group, di
C ₁ -C ₄ alkylamino group, a phenyl group, a benzyl group, a methylenedioxy group or halo methylenedioxy group, the substituent when the substituent is two or more may be different even in the same ) Is shown. }, M is an integer of 1 to 5 (provided that Y is the same or different in the case of 2 to 5), and Z is an oxygen atom, a sulfur atom or an imino group. ] It is related with the imidazolinone derivative represented by these, and the pest control agent which contains 1 type (s) or 2 or more types of this derivative as an active ingredient.

Examples of each substituent shown in the present specification are shown below. The carbon chain of each substituent may be linear, branched or cyclic. Hereinafter, n- is normal, i
-Is iso, sec- is secondary, t- is tertiary, and c- is cyclo.

The C ₁ -C ₆ alkyl group is a methyl group, ethyl group, n-propyl group, i-propyl group, c-propyl group, n-butyl group, i-butyl group, sec-butyl group, t -Butyl group, c-butyl group, n-pentyl group, c
-Pentyl group, n-hexyl group, c-hexyl group and the like.

Examples of the C ₂ -C ₆ alkenyl group include ethenyl group, 2-propenyl group, 2-methyl-2-propenyl group and 2-butenyl group.

Examples of the C ₂ -C ₆ alkynyl group include ethynyl group, 2-propynyl group and 2-butynyl group.

Examples of the C ₂ -C ₆ alkoxyalkyl group include methoxymethyl group, ethoxymethyl group and 1-methoxyethyl group.

The C ₂ -C ₆ alkylcarbonyl group includes a methylcarbonyl group, an ethylcarbonyl group, an n-propylcarbonyl group, an i-propylcarbonyl group, a c-propylcarbonyl group, an n-butylcarbonyl group and an i-butylcarbonyl group. Group, sec-butylcarbonyl group, t-butylcarbonyl group, c-butylcarbonyl group and the like.

As the C ₂ -C ₆ alkoxycarbonyl group,
Methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i-propoxycarbonyl group,
Examples thereof include a c-propoxycarbonyl group, an n-butoxycarbonyl group, an i-butoxycarbonyl group, a sec-butoxycarbonyl group, a t-butoxycarbonyl group and a c-butoxycarbonyl group.

Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

R ¹ is preferably a hydrogen atom or C _{1 to} C ₆
An alkyl group is mentioned.

R ² is preferably a hydrogen atom or C ₁ -C ₆
An alkyl group is mentioned.

X is preferably a halogen atom, C _1-
C ₆ haloalkyl group or a C ₁ -C ₆ alkoxy group.

Y is preferably a halogen atom, C _1-
C ₆ alkyl group, C _{1 to} C ₆ alkoxy group, C _{1 to} C ₆ haloalkyl group, C _{1 to} C ₆ haloalkoxy group, nitro group and optionally substituted pyridyloxy group (however, optionally substituted good examples of the substituent include a halogen atom, a cyano group, a nitro group, and a C ₁ -C ₆ haloalkyl groups and C ₁ -C ₆ haloalkoxy group).

As Z, an oxygen atom is preferable.

L is preferably an integer of 1 or 2.

M is preferably an integer of 1 to 3.

The following compounds are preferred as the compound of the present invention.

R ¹ and R ² are each independently a hydrogen atom or C _1-
Indicates C ₆ alkyl group, X is a halogen atom, C ₁ -C ₆ shows a haloalkyl group or a C ₁ -C ₆ alkoxy group, Y halogen atom, C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group , C ₁ ~
C ₆ haloalkyl group, C _{1 to} C ₆ haloalkoxy group, nitro group or optionally substituted pyridyloxy group (provided that the optionally substituted substituent is a halogen atom, a cyano group, a nitro group, C ₁ ~ C ₆ haloalkyl group or
C _{1 to} C ₆ represents a haloalkoxy group, Z represents an oxygen atom,
The imidazolinone derivative represented by the formula (I) in which l represents an integer of 1 or 2 and m represents an integer of 1 to 3.

Among the compounds included in the present invention, the compounds having an asymmetric carbon atom include optically active compounds S-form and R-form. Further, when there are configurational isomers, the E form and the Z form are included.

Specific examples of the compounds included in the present invention include the compounds shown in Table 1. However, the compounds in Table 1 are for exemplification, and the present invention is not limited to these.

Q1 to Q61 in Table 1 are groups represented by the following formula.

[0033]

[Chemical 7]

[0034]

Embedded image

[0035]

[Chemical 9]

Table 1

[0037]

[Chemical 10]

[0038]

[Table 1] ────────────────────────────────── R ¹ R ² X _l Y _m Z ─── ─────────────────────────────── H CH ₃ 2-Cl 4-FOH CH ₃ 2-Cl 2-Cl OH CH ₃ 2-Cl 3-Cl OH CH ₃ 2-Cl 4-Cl OH CH ₃ 2-Cl 4-Br OH CH ₃ 2-Cl 4-IOH CH ₃ 2-Cl 4-CH ₃ OH CH ₃ 2-Cl 4 -CH ₂ CH ₂ CH ₂ CH ₃ OH CH ₃ 2-Cl 4-C (CH ₃ ) ₃ OH CH ₃ 2-Cl 4-CH ₂ CH = CH ₂ OH CH ₃ 2-Cl 4-CH ₂ C≡CH OH CH ₃ 2-Cl 4-Q51 OH CH ₃ 2-Cl 4-Q52 OH CH ₃ 2-Cl 4-Q53 OH CH ₃ 2-Cl 4-Q54 OH CH ₃ 2-Cl 4-CHF ₂ OH CH ₃ 2 -Cl 4-CH ₂ Cl OH CH ₃ 2-Cl 2-CF ₃ OH CH ₃ 2-Cl 3-CF ₃ OH CH ₃ 2-Cl 4-CF ₃ OH CH ₃ 2-Cl 4-CH = C (Cl ) CF ₃ OH CH ₃ 2-Cl 4-CH ₂ C ≡ CBr OH CH ₃ 2-Cl 4- (Q54-1-Cl) O ─────────────────── ────────────────

[0039]

[Table 2] ────────────────────────────────── R ¹ R ² X _l Y _m Z ─── ─────────────────────────────── H CH ₃ 2-Cl 4-CH ₂ CN OH CH ₃ 2-Cl 4- CH ₂ OH OH CH ₃ 2-Cl 4-CH ₂ CO ₂ HOH CH ₃ 2-Cl 4-OCH ₃ OH CH ₃ 2-Cl 4-OCH ₂ CH ₃ OH CH ₃ 2-Cl 4-OCH ₂ CH = CH _{2 OH CH 3 2-Cl 4} -OCH 2 C≡CH OH CH 3 2-Cl 4-O (Q53) OH CH 3 2-Cl 4-O (Q54) OH CH 3 2-Cl 4-O (Q54- 2-CH (CH ₃ ) ₂ -5-CH ₃ ) OH CH ₃ 2-Cl 4-OCHF ₂ OH CH ₃ 2-Cl 4-OCF ₂ Br OH CH ₃ 2-Cl 2-OCF ₃ OH CH ₃ 2- Cl 3-OCF ₃ OH CH ₃ 2-Cl 4-OCF ₃ OH CH ₃ 2-Cl 4-OCH ₂ CF ₃ OH CH ₃ 2-Cl 4-OCF ₂ CHF ₂ OH CH ₃ 2-Cl 4-OCF ₂ CHFCl OH CH ₃ 2-Cl 4-OCF ₂ CHFCF ₃ OH CH ₃ 2-Cl 4-OCF ₂ CF ₂ CF ₃ OH CH ₃ 2-Cl 4-OCH ₂ CH = CHCl OH CH ₃ 2-Cl 4-OCH ₂ C ≡ CBr OH CH ₃ 2-Cl 4-O (Q51-2,2-Cl ₂ ) O ──────────────────────────── ──────

[0040]

[Table 3] ────────────────────────────────── R ¹ R ² X _l Y _m Z ─── ─────────────────────────────── H CH ₃ 2-Cl 4-OCH ₂ (Q51-2,2-Cl ₂ ) OH CH ₃ 2-Cl 4-SCH ₃ OH CH ₃ 2-Cl 4-SCH ₂ CH = CH ₂ OH CH ₃ 2-Cl 4-SCH ₂ C ≡ CH OH CH ₃ 2-Cl 4-S (Q54) OH CH ₃ 2-Cl 4-SCHF ₂ OH CH ₃ 2-Cl 4-SCF ₃ OH CH ₃ 2-Cl 4-SCF ₂ Cl OH CH ₃ 2-Cl 4-SOCH ₃ OH CH ₃ 2-Cl 4-SOCH ₂ CH = CH ₂ OH CH ₃ 2-Cl 4-SO (Q54) OH CH ₃ 2-Cl 4-SOCF ₃ OH CH ₃ 2-Cl 4-SO ₂ CH ₃ OH CH ₃ 2-Cl 4-SO ₂ CH ₂ CH = CH ₂ OH CH ₃ 2-Cl 4-SO ₂ CH ₂ C ≡ CH OH CH ₃ 2-Cl 4-SO ₂ (Q54) OH CH ₃ 2-Cl 4-SO ₂ CF ₃ OH CH ₃ 2- Cl 4-SO ₂ CF ₂ CHFCl OH CH ₃ 2-Cl 4-CH ₂ OCH ₃ OH CH ₃ 2-Cl 4-OCH ₂ CH ₂ OCH ₃ OH CH ₃ 2-Cl 4-CH ₂ OCH ₂ CF ₃ OH CH ₃ 2-Cl 4-OCF ₂ CHFOCF ₃ OH CH ₃ 2-Cl 4-CH ₂ SCH ₃ O ──────────────────────────── ───────

[0041]

[Table 4] ────────────────────────────────── R ¹ R ² X _l Y _m Z ─── ─────────────────────────────── H CH ₃ 2-Cl 4-OCH ₂ CH ₂ SCH ₃ OH CH ₃ 2- Cl 4-CH ₂ CO ₂ CH ₃ OH CH ₃ 2-Cl 4-CH ₂ CO ₂ CH ₂ CF ₃ OH CH ₃ 2-Cl 4-CH ₂ COCH ₃ OH CH ₃ 2-Cl 4-OCO ₂ CH ₃ OH CH ₃ 2-Cl 4-OCOCH ₃ OH CH ₃ 2-Cl 4-COCH ₃ OH CH ₃ 2-Cl 4-COCH ₂ CH = CH ₂ OH CH ₃ 2-Cl 4-CO (Q53) OH CH ₃ 2- Cl 4-COCF ₃ OH CH ₃ 2-Cl 4-CO ₂ CH ₂ CH ₃ OH CH ₃ 2-Cl 4-CO ₂ C (CH ₃ ) ₃ OH CH ₃ 2-Cl 4-CO ₂ CH ₂ CF ₃ OH CH ₃ 2-Cl 4-OCH ₂ CO ₂ CH ₃ OH CH ₃ 2-Cl 4-NO ₂ OH CH ₃ 2-Cl 4-CN OH CH ₃ 2-Cl 4-OH OH CH ₃ 2-Cl 4-CO ₂ HOH CH ₃ 2-Cl 4-SCN OH CH ₃ 2-Cl 4-NCS OH CH ₃ 2-Cl 4-CH ₂ SCN OH CH ₃ 2-Cl 4-OSO ₂ CH ₃ OH CH ₃ 2-Cl 4- CSCH ₃ O ──────────────────────────────────

[0042]

[Table 5] ────────────────────────────────── R ¹ R ² X _l Y _m Z ─── ─────────────────────────────── H CH ₃ 2-Cl 4-NH ₂ OH CH ₃ 2-Cl 4-N (CH ₃ ) ₂ OH CH ₃ 2-Cl 4-N (CH ₃ ) CH ₂ CH ₂ CH ₃ OH CH ₃ 2-Cl 4-N (CH ₃ ) CH ₂ CH = CHCl OH CH ₃ 2-Cl 4- N (CH ₃ ) CH ₂ C ₆ H ₅ OH CH ₃ 2-Cl 4-CON (CH ₃ ) ₂ OH CH ₃ 2-Cl 4-OCON (CH ₃ ) ₂ OH CH ₃ 2-Cl 4-NHCOCH ₃ OH CH ₃ 2-Cl 4-NHCO ₂ CH ₂ CH ₃ OH CH ₃ 2-Cl 4-SO ₂ N (CH ₃ ) ₂ OH CH ₃ 2-Cl 4-NHCSCH ₃ OH CH ₃ 2-Cl 4-Si (CH ₃ ) ₃ OH CH ₃ 2-Cl 3-OCH ₂ O-4 OH CH ₃ 2-Cl 3-OCF ₂ O-4 OH CH ₃ 2-Cl 3-OCH ₂ CH ₂ O-4 OH CH ₃ 2-Cl 3-OCF ₂ CF ₂ O-4 OH CH ₃ 2-Cl 4-C ₆ H ₅ OH CH ₃ 2-Cl 4- (C ₆ H ₄ -4-Cl) OH CH ₃ 2-Cl 4-OC ₆ H ₅ OH CH ₃ 2-Cl 4-O (C ₆ H ₄ -4-Cl) OH CH ₃ 2-Cl 4-O (C ₆ H ₄ -4-CF ₃ ) OH CH ₃ 2-Cl 4-O ( C ₆ H ₃ -2,4-Cl ₂ ) OH CH ₃ 2-Cl 4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) O ────────────── ───────────── ───────

[0043]

[Table 6] ────────────────────────────────── R ¹ R ² X _l Y _m Z ─── ─────────────────────────────── H CH ₃ 2-Cl 3-O (C ₆ H ₃ -2-Cl- 4-CF ₃ ) OH CH ₃ 2-Cl 4-S (C ₆ H ₃ -2-Cl-4-CF ₃ ) OH CH ₃ 2-Cl 4-NH (C ₆ H ₃ -2-Cl-4- CF ₃ ) OH CH ₃ 2-Cl 4-N (CH ₂ CH ₂ CH ₃ ) (C ₆ H ₄ -4-Cl) OH CH ₃ 2-Cl 4-CH ₂ C ₆ H ₅ OH CH ₃ 2-Cl 4-CF ₂ (C ₆ H ₄ -4-Br) OH CH ₃ 2-Cl 4-COC ₆ H ₅ OH CH ₃ 2-Cl 4-OCH ₂ (C ₆ H ₄ -4-CF ₃ ) OH CH ₃ 2-Cl 4-CH ₂ OC ₆ H ₅ OH CH ₃ 2-Cl 4-NHCH ₂ C ₆ H ₅ OH CH ₃ 2-Cl 4-CH ₂ CH ₂ C ₆ H ₅ OH CH ₃ 2-Cl 4-CH = CH (C ₆ H ₄ -4-Cl) OH CH ₃ 2-Cl 4-N = NC ₆ H ₅ OH CH ₃ 2-Cl 4-OCH ₂ CH ₂ C ₆ H ₅ OH CH ₃ 2-Cl 4- NHCON (CH ₃ ) (C ₆ H ₄ -4-Cl) OH CH ₃ 2-Cl 4-NHCSNHC ₆ H ₅ OH CH ₃ 2-Cl 4-OCH ₂ CH ₂ O (C ₆ H ₃ -2,4- Cl ₂ ) OH CH ₃ 2-Cl 4-CH ₂ ON = C (Q51) (C ₆ H ₄ -4-Cl) OH CH ₃ 2-Cl 4-O (Q1-1-CH ₃ ) OH CH ₃ 2 -Cl 4-O (Q2-1-CH ₃ ) OH CH ₃ 2-Cl 4- (Q3) OH CH ₃ 2-Cl 4-CH ₂ (Q4) OH CH ₃ 2 -Cl 4- (Q5) O ───────────────────────────────────

[0044]

[Table 7] ────────────────────────────────── R ¹ R ² X _l Y _m Z ─── ─────────────────────────────── H CH ₃ 2-Cl 4-C≡C (Q6) OH CH ₃ 2- Cl 4-CH ₂ (Q7) OH CH ₃ 2-Cl 4- (Q8-3,5- (CF ₃ ) ₂ ) OH CH ₃ 2-Cl 4- (Q8-3-C ₆ H ₅ ) OH CH ₃ 2-Cl 4-OCH ₂ (Q9-1-CH ₃ ) OH CH ₃ 2-Cl 4-O (Q10-1-CH ₃ ) OH CH ₃ 2-Cl 4- (Q11-1-C ₆ H ₅ ) OH CH ₃ 2-Cl 4- (Q12-1-CH ₃ ) OH CH ₃ 2-Cl 4-OCH ₂ (Q13-1-CH ₃ ) OH CH ₃ 2-Cl 4-O (Q14-1-CH ₃ ) OH CH ₃ 2-Cl 4- (Q15) OH CH ₃ 2-Cl 4-O (Q16) OH CH ₃ 2-Cl 4-O (Q17-5-CH ₃ ) OH CH ₃ 2-Cl 4-O (Q18) OH CH ₃ 2-Cl 4-OCH ₂ (Q19) OH CH ₃ 2-Cl 4-OCH ₂ (Q20-4-Cl) OH CH ₃ 2-Cl 4- (Q21) OH CH ₃ 2-Cl 4-OCH ₂ (Q22) OH CH ₃ 2-Cl 4- (Q23) OH CH ₃ 2-Cl 4-OCH ₂ (Q24) OH CH ₃ 2-Cl 4-O (Q25-3-CH ₃ ) OH CH ₃ 2-Cl 4- (Q26-1-CH ₃ ) OH CH ₃ 2-Cl 4-OCH ₂ (Q27-1-CH ₃ ) O ────────────────── ─────────────────

[0045]

[Table 8] ────────────────────────────────── R ¹ R ² X _l Y _m Z ─── ─────────────────────────────── H CH ₃ 2-Cl 4-OCH ₂ (Q28-1-CH ₃ ) OH CH ₃ 2-Cl 4-O (Q29-1-CH ₃ ) OH CH ₃ 2-Cl 4-NHCONH (Q30) OH CH ₃ 2-Cl 4-O (Q31) OH CH ₃ 2-Cl 4-OCH ₂ (Q32) OH CH ₃ 2-Cl 4-OCH ₂ (Q33) OH CH ₃ 2-Cl 4-O (Q34) OH CH ₃ 2-Cl 4-O (Q36) OH CH ₃ 2-Cl 4-OCH ₂ (Q37-5-Cl) OH CH ₃ 2-Cl 3-O (Q38-3-Cl-5-CF ₃ ) OH CH ₃ 2-Cl 4-O (Q38-3,5-Cl ₂ ) OH CH ₃ 2-Cl 4-O (Q38-3-Cl-5-CF ₃ ) OH CH ₃ 2-Cl 4-NH (Q38-5-CF ₃ ) OH CH ₃ 2-Cl 4- (Q38-3-Cl- 5-CF ₃ ) OH CH ₃ 2-Cl 4-O (Q39-5-Br) OH CH ₃ 2-Cl 4-O (Q40-2,6-Cl ₂ ) OH CH ₃ 2-Cl 4-O ( Q41-6-Cl) OH CH ₃ 2-Cl 4-O (Q42) OH CH ₃ 2-Cl 4-O (Q43-5-Cl) OH CH ₃ 2-Cl 4-O (Q44) OH CH ₃ 2 -Cl 4-O (Q45-4-CF ₃ -6-Cl) OH CH ₃ 2-Cl 4-O (Q46) OH CH ₃ 2-Cl 4-O (Q47) O ───────── ──────────────────────────

[0046]

[Table 9] ────────────────────────────────── R ¹ R ² X _l Y _m Z ─── ─────────────────────────────── H CH ₃ 2-Cl 4-O (Q47-4-Cl) OH CH ₃ 2-Cl 4-O (Q48) OH CH ₃ 2-Cl 4-O (Q49) OH CH ₃ 2-Cl 3-O (Q50-6-Cl) OH CH ₃ 2-Cl 3-O (Q50-6 -CF ₃ ) OH CH ₃ 2-Cl 2,4-F ₂ OH CH ₃ 2-Cl 2,3-Cl ₂ OH CH ₃ 2-Cl 2,4-Cl ₂ OH CH ₃ 2-Cl 2,5- Cl ₂ OH CH ₃ 2-Cl 2,6-Cl ₂ OH CH ₃ 2-Cl 3,4-Cl ₂ OH CH ₃ 2-Cl 3,5-Cl ₂ OH CH ₃ 2-Cl 3,4-Br ₂ OH CH ₃ 2-Cl 3,4-I ₂ OH CH ₃ 2-Cl 2,4- (CH ₃ ) ₂ OH CH ₃ 2-Cl 3,4- (OCH ₃ ) ₂ OH CH ₃ 2-Cl 2- F-4-Cl OH CH ₃ 2-Cl 2-F-4-Br OH CH ₃ 2-Cl 2-F-4-OCF ₃ OH CH ₃ 2-Cl 2-F-4-OCF ₂ CHF ₂ OH CH ₃ 2-Cl 2-F-4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) OH CH ₃ 2-Cl 2-F-4-O (Q38-3-Cl-5-CF ₃ ) OH CH ₃ 2-Cl 3-F-4-Cl O ───────────────────────────────────

[0047]

[Table 10] ────────────────────────────────── R ¹ R ² X _l Y _m Z ─── ─────────────────────────────── H CH ₃ 2-Cl 3-F-4-O (Q38-3-Cl -5-CF ₃ ) OH CH ₃ 2-Cl 2-Cl-4-CF ₃ OH CH ₃ 2-Cl 2-Cl-4-O (Q38-3-Cl-5-CF ₃ ) OH CH ₃ 2- Cl 2-Cl-5-O (Q50-6-Cl) OH CH ₃ 2-Cl 3-Cl-4-Br OH CH ₃ 2-Cl 3-Cl-4-CF ₃ OH CH ₃ 2-Cl 3- Cl-4-OCF ₃ OH CH ₃ 2-Cl 3-Cl-4-OCF ₂ CHF ₂ OH CH ₃ 2-Cl 3-Cl-4-O (C ₆ H ₄ -4-CF ₃ ) OH CH ₃ 2 -Cl 3-Cl-4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) OH CH ₃ 2-Cl 3-Cl-4-O (Q38-3-Cl-5-CF ₃ ) OH CH ₃ 2-Cl 3-CF ₃ -4-Cl OH CH ₃ 2-Cl 3-CH ₃ -4-Br OH CH ₃ 2-Cl 3-OCH ₃ -4-CF ₃ OH CH ₃ 2-Cl 3- CF ₃ -4-Br OH CH ₃ 2-Cl 3-Cl-4-IOH CH ₃ 2-Cl 3-Cl-4-FOH CH ₃ 2-Cl 3-Cl-4-CH ₃ OH CH ₃ 2-Cl 2,3,4-F ₃ OH CH ₃ 2-Cl 2,4,5-F ₃ OH CH ₃ 2-Cl 2,5-F ₂ -4-Cl OH CH ₃ 2-Cl 3,5-F ₂ -4-CF ₃ OH CH ₃ 2-Cl 2,5-Cl ₂ -4-OCF ₂ CHF ₂ O ────────────────────────── ─ ───────

[0048]

[Table 11] ────────────────────────────────── R ¹ R ² X _l Y _m Z ─── ─────────────────────────────── H CH ₃ 2-Cl 2,6-Cl ₂ -4-CF ₃ OH CH ₃ 2-Cl 2,4,5-Cl ₃ OH CH ₃ 2-Cl 3,4,5-Cl ₃ OH CH ₃ 2-Cl 3,5-Cl ₂ -4-OCF ₃ OH CH ₃ 2-Cl 3 , 5-Cl ₂ -4-OCF ₂ CHF ₂ OH CH ₃ 2-Cl 3,5-Cl ₂ -4-O (C ₆ H ₄ -4-Cl) OH CH ₃ 2-Cl 3,5-Cl ₂ -4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) OH CH ₃ 2-Cl 3,5-Cl ₂ -4-NH (C ₆ H ₄ -4-CF ₃ ) OH CH ₃ 2 -Cl 3,5-Cl ₂ -4-O (Q38-3-Cl-5-CF ₃ ) OH CH ₃ 2-Cl 3,5-Cl ₂ -4-O (Q50-6-CF ₃ ) OH CH ₃ 2-Cl 2-F-4,5-Cl ₂ OH CH ₃ 2-Cl 2-F-4-OCF ₂ CHF ₂ -5-Cl OH CH ₃ 2-Cl 2,3,4,5-F ₄ OH CH ₃ 2-Cl 2,4-F ₂ -3,5-Cl ₂ OH CH ₃ 2-Cl 2,6-F ₂ -3,5-Cl ₂ OH CH ₃ 2-Cl 2,3,4, 5,6-F ₅ OH CH ₃ 2-Cl 4-OCH ₂ CH ₂ CH ₂ CH ₃ OH CH ₃ 2-Cl 3-F-4-CH ₃ OH CH ₃ 2-Cl 2-Br-4-OCF ₃ OH CH ₃ 2-Cl 4- (CH ₂ ) ₅ CH ₃ OH CH ₃ 2-Cl 2-CH ₃ -4-OCF ₃ OH CH ₃ 2-Cl 4-OCOC ₆ H ₅ OH CH ₃ 2-Cl 4- OSO ₂ C ₆ H ₅ O ──── ─────────────────────────────

[0049]

[Table 12] ────────────────────────────────── R ¹ R ² X _l Y _m Z ─── ─────────────────────────────── H CH ₃ 2-Cl 4-CF ₂ CF ₃ OH CH ₃ 2,6- F ₂ 3-FOH CH ₃ 2,6-F ₂ 4-FOH CH ₃ 2,6-F ₂ 2-Cl OH CH ₃ 2,6-F ₂ 3-Cl OH CH ₃ 2,6-F ₂ 4- Cl OH CH ₃ 2,6-F ₂ 4-Br OH CH ₃ 2,6-F ₂ 4-IOH CH ₃ 2,6-F ₂ 4-CH ₃ OH CH ₃ 2,6-F ₂ 4-C ( CH ₃ ) ₃ OH CH ₃ 2,6-F ₂ 4-CHF ₂ OH CH ₃ 2,6-F ₂ 3-CF ₃ OH CH ₃ 2,6-F ₂ 4-CF ₃ OH CH ₃ 2,6- F ₂ 4-OCH ₃ OH CH ₃ 2,6-F ₂ 4-OCH ₂ CH ₃ OH CH ₃ 2,6-F ₂ 4-OCHF ₂ OH CH ₃ 2,6-F ₂ 4-OCF ₂ Br OH CH ₃ 2,6-F ₂ 2-OCF ₃ OH CH ₃ 2,6-F ₂ 3-OCF ₃ OH CH ₃ 2,6-F ₂ 4-OCF ₃ OH CH ₃ 2,6-F ₂ 4-OCH ₂ CF ₃ OH CH ₃ 2,6-F ₂ 4-OCF ₂ CHF ₂ OH CH ₃ 2,6-F ₂ 4-OCF ₂ CHFCl O ─────────────────── ────────────────

[0050]

[Table 13] ────────────────────────────────── R ¹ R ² X _l Y _m Z ─── ─────────────────────────────── H CH ₃ 2,6-F ₂ 4-SCH ₃ OH CH ₃ 2,6 -F ₂ 4-SCHF ₂ OH CH ₃ 2,6-F ₂ 4-SCF ₃ OH CH ₃ 2,6-F ₂ 4-SCF ₂ Cl OH CH ₃ 2,6-F ₂ 4-SOCH ₃ OH CH ₃ 2,6-F ₂ 4-SOCF ₃ OH CH ₃ 2,6-F ₂ 4-SO ₂ CH ₃ OH CH ₃ 2,6-F ₂ 4-SO ₂ CF ₃ OH CH ₃ 2,6-F ₂ 4 -SO ₂ CF ₂ CHFCl OH CH ₃ 2,6-F ₂ 4-OCF ₂ CHFOCF ₃ OH CH ₃ 2,6-F ₂ 4-COCH ₃ OH CH ₃ 2,6-F ₂ 4-COCF ₃ OH CH ₃ 2,6-F ₂ 4-CO ₂ CH ₂ CH ₃ OH CH ₃ 2,6-F ₂ 4-NO ₂ OH CH ₃ 2,6-F ₂ 4-CN OH CH ₃ 2,6-F ₂ 4- CO ₂ HOH CH ₃ 2,6-F ₂ 4-N (CH ₃ ) CH ₂ CH ₂ CH ₃ OH CH ₃ 2,6-F ₂ 4-NHCOCH ₃ OH CH ₃ 2,6-F ₂ 3-OCH ₂ O-4 OH CH ₃ 2,6-F ₂ 3-OCF ₂ O-4 OH CH ₃ 2,6-F ₂ 3-OCF ₂ CF ₂ O-4 OH CH ₃ 2,6-F ₂ 4-C ₆ H ₅ OH CH ₃ 2,6-F ₂ 4- (C ₆ H ₄ -4-Cl) O ─────────────────────────── ────────

[0051]

[Table 14] ────────────────────────────────── R ¹ R ² X _l Y _m Z ─── ─────────────────────────────── H CH ₃ 2,6-F ₂ 4-O (C ₆ H ₄ -4 -Cl) OH CH ₃ 2,6-F ₂ 4-O (C ₆ H ₄ -4-CF ₃ ) OH CH ₃ 2,6-F ₂ 4-O (C ₆ H ₃ -2,4-Cl ₂ ) OH CH ₃ 2,6-F ₂ 4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) OH CH ₃ 2,6-F ₂ 3-O (C ₆ H ₃ -2-Cl- 4-CF ₃ ) OH CH ₃ 2,6-F ₂ 4-OCH ₂ (C ₆ H ₄ -4-CF ₃ ) OH CH ₃ 2,6-F ₂ 4-CH ₂ ON = C (Q51) (C ₆ H ₄ -4-Cl) OH CH ₃ 2,6-F ₂ 3-O (Q38-3-Cl-5-CF ₃ ) OH CH ₃ 2,6-F ₂ 4-O (Q38-3,5 -Cl ₂ ) OH CH ₃ 2,6-F ₂ 4-O (Q38-3-Cl-5-CF ₃ ) OH CH ₃ 2,6-F ₂ 4- (Q38-3-Cl-5-CF ₃ ) OH CH ₃ 2,6-F ₂ 4-O (Q39-5-Br) OH CH ₃ 2,6-F ₂ 4-O (Q40-2,6-Cl ₂ ) OH CH ₃ 2,6-F ₂ 4-O (Q45-4-CF ₃ -6-Cl) OH CH ₃ 2,6-F ₂ 3-O (Q50-6-Cl) OH CH ₃ 2,6-F ₂ 2,4-F ₂ OH CH ₃ 2,6-F ₂ 2,4-Cl ₂ OH CH ₃ 2,6-F ₂ 2,5-Cl ₂ OH CH ₃ 2,6-F ₂ 3,4-Cl ₂ OH CH ₃ 2, 6-F ₂ 3,5-Cl ₂ OH CH ₃ 2,6-F ₂ 3,4-Br ₂ OH CH ₃ 2,6-F ₂ 2-F-4-Cl OH CH ₃ 2,6-F ₂ 2-F-4-Br O ──────────────────────────────────

[0052]

[Table 15] ────────────────────────────────── R ¹ R ² X _l Y _m Z ─── ─────────────────────────────── H CH ₃ 2,6-F ₂ 2-F-4-OCF ₃ OH CH ₃ 2,6-F ₂ 2-F-4-OCF ₂ CHF ₂ OH CH ₃ 2,6-F ₂ 2-F-4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) OH CH ₃ 2,6-F ₂ 2-F-4-O (Q38-3-Cl-5-CF ₃ ) OH CH ₃ 2,6-F ₂ 3-F-4-Cl OH CH ₃ 2,6-F ₂ 3-F-4-O (Q38-3-Cl-5-CF ₃ ) OH CH ₃ 2,6-F ₂ 2-Cl-4-CF ₃ OH CH ₃ 2,6-F ₂ 2-Cl- 4-O (Q38-3-Cl-5-CF ₃ ) OH CH ₃ 2,6-F ₂ 3-Cl-4-Br OH CH ₃ 2,6-F ₂ 3-Cl-4-CF ₃ OH CH ₃ 2,6-F ₂ 3-Cl-4-OCF ₃ OH CH ₃ 2,6-F ₂ 3-Cl-4-OCF ₂ CHF ₂ OH CH ₃ 2,6-F ₂ 3-Cl-4-O (C ₆ H ₄ -4-CF ₃ ) OH CH ₃ 2,6-F ₂ 3-Cl-4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) OH CH ₃ 2,6-F ₂ 3-Cl-4-O (Q38-3-Cl-5-CF ₃ ) OH CH ₃ 2,6-F ₂ 3-Cl-4-IOH CH ₃ 2,6-F ₂ 2,3,4- F ₃ OH CH ₃ 2,6-F ₂ 2,4,5-F ₃ OH CH ₃ 2,6-F ₂ 2,5-F ₂ -4-Cl OH CH ₃ 2,6-F ₂ 2-F -4,5-Cl ₂ OH CH ₃ 2,6-F ₂ 2,5-Cl ₂ -4-OCF ₂ CHF ₂ OH CH ₃ 2,6-F ₂ 2,4,5-Cl ₃ OH CH ₃ 2 , 6-F ₂ 3, 4,5-Cl ₃ O ───────────────────────────────────

[0053]

[Table 16] ────────────────────────────────── R ¹ R ² X _l Y _m Z ─── ─────────────────────────────── H CH ₃ 2,6-F ₂ 3,5-Cl ₂ -4-OCF ₃ OH CH ₃ 2,6-F ₂ 3,5-Cl ₂ -4-OCF ₂ CHF ₂ OH CH ₃ 2,6-F ₂ 3,5-Cl ₂ -4-O (C ₆ H ₄ -4- Cl) OH CH ₃ 2,6-F ₂ 3,5-Cl ₂ -4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) OH CH ₃ 2,6-F ₂ 3,5-Cl ₂ -4-O (Q38-3-Cl-5-CF ₃ ) OH CH ₃ 2,6-F ₂ 3,5-Cl ₂ -4-O (Q50-6-CF ₃ ) OH CH ₃ 2,6 -F ₂ 2,4-F ₂ -3,5-Cl ₂ OH CH ₃ 2,6-F ₂ 2,3,4,5,6-F ₅ OH CH ₃ 2,6-F ₂ 4-CF ₂ CF ₃ OH CH ₃ 2-F 4-FOH CH ₃ 2-F 4-Cl OH CH ₃ 2-F 4-Br OH CH ₃ 2-F 4-IOH CH ₃ 2-F 4-CF ₃ OH CH ₃ 2 -F 4-OCHF ₂ OH CH ₃ 2-F 4-OCF ₂ Br OH CH ₃ 2-F 3-OCF ₃ OH CH ₃ 2-F 4-OCF ₃ OH CH ₃ 2-F 4-OCF ₂ CHF ₂ OH CH ₃ 2-F 4-SCF ₃ OH CH ₃ 2-F 4-SO ₂ CH ₃ OH CH ₃ 2-F 4-SO ₂ CF ₃ OH CH ₃ 2-F 4-NO ₂ O ────── ────────────────────────────

[0054]

[Table 17] ────────────────────────────────── R ¹ R ² X _l Y _m Z ─── ─────────────────────────────── H CH ₃ 2-F 4-CN OH CH ₃ 2-F 3-OCF ₂ O-4 OH CH ₃ 2-F 4- (C ₆ H ₄ -4-Cl) OH CH ₃ 2-F 4-O (C ₆ H ₄ -4-CF ₃ ) OH CH ₃ 2-F 4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) OH CH ₃ 2-F 4-CH ₂ ON = C (Q51) (C ₆ H ₄ -4-Cl) OH CH ₃ 2-F 4-O (Q38-3-Cl-5-CF ₃ ) OH CH ₃ 2-F 4- (Q38-3-Cl-5-CF ₃ ) OH CH ₃ 2-F 3-O (Q50-6-Cl) OH CH ₃ 2-F 2,4-F ₂ OH CH ₃ 2-F 2,4-Cl ₂ OH CH ₃ 2-F 3,4-Cl ₂ OH CH ₃ 2-F 3,5-Cl ₂ OH CH ₃ 2 -F 3,4-Br ₂ OH CH ₃ 2-F 2-F-4-Cl OH CH ₃ 2-F 2-F-4-Br OH CH ₃ 2-F 2-F-4-OCF ₃ OH CH ₃ 2-F 2-F-4-OCF ₂ CHF ₂ OH CH ₃ 2-F 2-F-4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) OH CH ₃ 2-F 2- F-4-O (Q38-3-Cl-5-CF ₃ ) OH CH ₃ 2-F 3-F-4-Cl OH CH ₃ 2-F 3-Cl-4-Br OH CH ₃ 2-F 3 -Cl-4-CF ₃ O ───────────────────────────────────

[0055]

[Table 18] ────────────────────────────────── R ¹ R ² X _l Y _m Z ─── ─────────────────────────────── H CH ₃ 2-F 3-Cl-4-OCF ₃ OH CH ₃ 2- F 3-Cl-4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) OH CH ₃ 2-F 3-Cl-4-O (Q38-3-Cl-5-CF ₃ ) OH CH ₃ 2-F 3-Cl-4-IOH CH ₃ 2-F 2,3,4-F ₃ OH CH ₃ 2-F 2,4,5-F ₃ OH CH ₃ 2-F 2,5-F ₂ -4-Cl OH CH ₃ 2-F 2-F-4,5-Cl ₂ OH CH ₃ 2-F 2,4,5-Cl ₃ OH CH ₃ 2-F 3,4,5-Cl ₃ OH CH ₃ 2-F 3,5-Cl ₂ -4-OCF ₂ CHF ₂ OH CH ₃ 2-F 3,5-Cl ₂ -4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) OH CH ₃ 2-F 3,5-Cl ₂ -4-O (Q38-3-Cl-5-CF ₃ ) OH CH ₃ 2-F 2,4-F ₂ -3,5-Cl ₂ OH CH ₃ 2- F 4-CF ₂ CF ₃ OH CH ₃ 2-Cl-6-F 4-FOH CH ₃ 2-Cl-6-F 4-Cl OH CH ₃ 2-Cl-6-F 4-Br OH CH ₃ 2- Cl-6-F 4-IOH CH ₃ 2-Cl-6-F 4-CF ₃ OH CH ₃ 2-Cl-6-F 4-OCHF ₂ OH CH ₃ 2-Cl-6-F 4-OCF ₂ Br OH CH ₃ 2-Cl-6-F 4-OCF ₃ O ───────────────────────────────────

[0056]

[Table 19] ────────────────────────────────── R ¹ R ² X _l Y _m Z ─── ─────────────────────────────── H CH ₃ 2-Cl-6-F 4-OCF ₂ CHF ₂ OH CH ₃ 2-Cl-6-F 4-SCF ₃ OH CH ₃ 2-Cl-6-F 4-SO ₂ CF ₃ OH CH ₃ 2-Cl-6-F 4-NO ₂ OH CH ₃ 2-Cl-6- F 4-CN OH CH ₃ 2-Cl-6-F 3-OCF ₂ O-4 OH CH ₃ 2-Cl-6-F 4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) OH CH ₃ 2-Cl-6-F 4-CH ₂ ON = C (Q51) (C ₆ H ₄ -4-Cl) OH CH ₃ 2-Cl-6-F 4-O (Q38-3-Cl-5 -CF ₃ ) OH CH ₃ 2-Cl-6-F 3,4-Cl ₂ OH CH ₃ 2-Cl-6-F 3,5-Cl ₂ OH CH ₃ 2-Cl-6-F 3,4- Br ₂ OH CH ₃ 2-Cl-6-F 2-F-4-Cl OH CH ₃ 2-Cl-6-F 2-F-4-Br OH CH ₃ 2-Cl-6-F 2-F- 4-OCF ₃ OH CH ₃ 2-Cl-6-F 2-F-4-OCF ₂ CHF ₂ OH CH ₃ 2-Cl-6-F 2-F-4-O (C ₆ H ₃ -2-Cl -4-CF ₃ ) OH CH ₃ 2-Cl-6-F 2-F-4-O (Q38-3-Cl-5-CF ₃ ) OH CH ₃ 2-Cl-6-F 3-F-4 -Cl OH CH ₃ 2-Cl-6-F 3-Cl-4-Br OH CH ₃ 2-Cl-6-F 3-Cl-4-OCF ₃ OH CH ₃ 2-Cl-6-F 2,5 _{-F 2 -4-Cl OH CH 3} 2-Cl-6-F 2-F-4,5-Cl 2 O ──────────── ─────────────────────

[0057]

[Table 20] ────────────────────────────────── R ¹ R ² X _l Y _m Z ─── ─────────────────────────────── H CH ₃ 2-Cl-6-F 3,4,5-Cl ₃ OH CH ₃ 2-Cl-6-F 3,5-Cl ₂ -4-OCF ₂ CHF ₂ OH CH ₃ 2-Cl-6-F 3,5-Cl ₂ -4-O (Q38-3-Cl-5 -CF ₃ ) OH CH ₃ 2-Cl-6-F 2,4-F ₂ -3,5-Cl ₂ OH CH ₃ 2-Cl-6-F 4-CF ₂ CF ₃ OH CH ₃ 2,6- Cl ₂ 4-FOH CH ₃ 2,6-Cl ₂ 4-Cl OH CH ₃ 2,6-Cl ₂ 4-Br OH CH ₃ 2,6-Cl ₂ 4-IOH CH ₃ 2,6-Cl ₂ 4- CF ₃ OH CH ₃ 2,6-Cl ₂ 4-OCHF ₂ OH CH ₃ 2,6-Cl ₂ 4-OCF ₂ Br OH CH ₃ 2,6-Cl ₂ 4-OCF ₃ OH CH ₃ 2,6-Cl ₂ 4-OCF ₂ CHF ₂ OH CH ₃ 2,6-Cl ₂ 4-SCF ₃ OH CH ₃ 2,6-Cl ₂ 4-SO ₂ CF ₃ OH CH ₃ 2,6-Cl ₂ 4-NO ₂ OH CH ₃ 2,6-Cl ₂ 4-CN OH CH ₃ 2,6-Cl ₂ 3-OCF ₂ O-4 OH CH ₃ 2,6-Cl ₂ 4-O (C ₆ H ₃ -2-Cl-4- CF ₃ ) OH CH ₃ 2,6-Cl ₂ 4-CH ₂ ON = C (Q51) (C ₆ H ₄ -4-Cl) OH CH ₃ 2,6-Cl ₂ 4-O (Q38-3-Cl -5-CF ₃ ) OH CH ₃ 2,6-Cl ₂ 3,4-Cl ₂ O ──────────────────────── ──────────

[0058]

[Table 21] ────────────────────────────────── R ¹ R ² X _l Y _m Z ─── ─────────────────────────────── H CH ₃ 2,6-Cl ₂ 3,5-Cl ₂ OH CH ₃ 2 , 6-Cl ₂ 3,4-Br ₂ OH CH ₃ 2,6-Cl ₂ 2-F-4-Cl OH CH ₃ 2,6-Cl ₂ 2-F-4-Br OH CH ₃ 2,6- Cl ₂ 2-F-4-OCF ₃ OH CH ₃ 2,6-Cl ₂ 2-F-4-OCF ₂ CHF ₂ OH CH ₃ 2,6-Cl ₂ 2-F-4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) OH CH ₃ 2,6-Cl ₂ 2-F-4-O (Q38-3-Cl-5-CF ₃ ) OH CH ₃ 2,6-Cl ₂ 3-F -4-Cl OH CH ₃ 2,6-Cl ₂ 3-Cl-4-Br OH CH ₃ 2,6-Cl ₂ 3-Cl-4-OCF ₃ OH CH ₃ 2,6-Cl ₂ 2,5- F ₂ -4-Cl OH CH ₃ 2,6-Cl ₂ 2-F-4,5-Cl ₂ OH CH ₃ 2,6-Cl ₂ 3,4,5-Cl ₃ OH CH ₃ 2,6-Cl ₂ 3,5-Cl ₂ -4-OCF ₂ CHF ₂ OH CH ₃ 2,6-Cl ₂ 3,5-Cl ₂ -4-O (Q38-3-Cl-5-CF ₃ ) OH CH ₃ 2, 6-Cl ₂ 2,4-F ₂ -3,5-Cl ₂ OH CH ₃ 2,6-Cl ₂ 4-CF ₂ CF ₃ OH CH ₃ 2-Br 4-Cl OH CH ₃ 2-Br 4-Br OH CH ₃ 2-Br 4-CF ₃ OH CH ₃ 2-Br 4-OCF ₃ OH CH ₃ 2-Br 4-OCF ₂ CHF ₂ O ────────────────── ────── ──────────

[0059]

[Table 22] ────────────────────────────────── R ¹ R ² X _l Y _m Z ─── ─────────────────────────────── H CH ₃ 2-Br 3-OCF ₂ O-4 OH CH ₃ 2-Br 4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) OH CH ₃ 2-Br 4-CH ₂ ON = C (Q51) (C ₆ H ₄ -4-Cl) OH CH ₃ 2-Br 4-O (Q38-3-Cl-5-CF ₃ ) OH CH ₃ 2-Br 3,4-Cl ₂ OH CH ₃ 2-Br 3,5-Cl ₂ OH CH ₃ 2-Br 3,4-Br ₂ OH CH ₃ 2-Br 2-F-4-Cl OH CH ₃ 2-Br 2-F-4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) OH CH ₃ 2-Br 2- F-4-O (Q38-3-Cl-5-CF ₃ ) OH CH ₃ 2-Br 3-F-4-Cl OH CH ₃ 2-Br 3-Cl-4-Br OH CH ₃ 2-Br 2 , 5-F ₂ -4-Cl OH CH ₃ 2-Br 3,4,5-Cl ₃ OH CH ₃ 2-Br 3,5-Cl ₂ -4-OCF ₂ CHF ₂ OH CH ₃ 2-Br 3, 5-Cl ₂ -4-O (Q38-3-Cl-5-CF ₃ ) OH CH ₃ 2-Br 2,4-F ₂ -3,5-Cl ₂ OH CH ₃ 2-CH ₃ 4-Cl OH CH ₃ 2-CH ₃ 4-Br OH CH ₃ 2-CH ₃ 4-CF ₃ OH CH ₃ 2-CH ₃ 4-OCF ₃ OH CH ₃ 2-CH ₃ 4-OCF ₂ CHF ₂ OH CH ₃ 2-CH ₃ 3-OCF ₂ O-4 O ──────────────────────────────── ───

[0060]

[Table 23] ────────────────────────────────── R ¹ R ² X _l Y _m Z ─── ─────────────────────────────── H CH ₃ 2-CH ₃ 4-O (C ₆ H ₃ -2-Cl -4-CF ₃ ) OH CH ₃ 2-CH ₃ 4-CH ₂ ON = C (Q51) (C ₆ H ₄ -4-Cl) OH CH ₃ 2-CH ₃ 4-O (Q38-3-Cl- 5-CF ₃ ) OH CH ₃ 2-CH ₃ 3,4-Cl ₂ OH CH ₃ 2-CH ₃ 3,5-Cl ₂ OH CH ₃ 2-CH ₃ 3,4-Br ₂ OH CH ₃ 2-CH ₃ 2-F-4-Cl OH CH ₃ 2-CH ₃ 2-F-4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) OH CH ₃ 2-CH ₃ 2-F-4- O (Q38-3-Cl-5-CF ₃ ) OH CH ₃ 2-CH ₃ 3-F-4-Cl OH CH ₃ 2-CH ₃ 3-Cl-4-Br OH CH ₃ 2-CH ₃ 2, 5-F ₂ -4-Cl OH CH ₃ 2-CH ₃ 3,4,5-Cl ₃ OH CH ₃ 2-CH ₃ 3,5-Cl ₂ -4-OCF ₂ CHF ₂ OH CH ₃ 2-CH ₃ 3,5-Cl ₂ -4-O (Q38-3-Cl-5-CF ₃ ) OH CH ₃ 2-CH ₃ 2,4-F ₂ -3,5-Cl ₂ OH CH ₃ 2-OCH ₃ 4 -Cl OH CH ₃ 2-OCH ₃ 4-Br OH CH ₃ 2-OCH ₃ 4-CF ₃ OH CH ₃ 2-OCH ₃ 4-OCF ₃ OH CH ₃ 2-OCH ₃ 4-OCF ₂ CHF ₂ OH CH _{3 2-OCH 3 3-OCF 2} O-4 OH CH 3 2-OCH 3 4-O (C 6 H 3 -2-Cl-4-CF 3) O ──────────── ─────────────────────

[0061]

[Table 24] ────────────────────────────────── R ¹ R ² X _l Y _m Z ─── ─────────────────────────────── H CH ₃ 2-OCH ₃ 4-CH ₂ ON = C (Q51) (C ₆ H ₄ -4-Cl) OH CH ₃ 2-OCH ₃ 4-O (Q38-3-Cl-5-CF ₃ ) OH CH ₃ 2-OCH ₃ 3,4-Cl ₂ OH CH ₃ 2-OCH ₃ 3,5-Cl ₂ OH CH ₃ 2-OCH ₃ 3,4-Br ₂ OH CH ₃ 2-OCH ₃ 2-F-4-Cl OH CH ₃ 2-OCH ₃ 2-F-4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) OH CH ₃ 2-OCH ₃ 2-F-4-O (Q38-3-Cl-5-CF ₃ ) OH CH ₃ 2-OCH ₃ 3-F-4 -Cl OH CH ₃ 2-OCH ₃ 3-Cl-4-Br OH CH ₃ 2-OCH ₃ 2,5-F ₂ -4-Cl OH CH ₃ 2-OCH ₃ 3,4,5-Cl ₃ OH CH ₃ 2-OCH ₃ 3,5-Cl ₂ -4-OCF ₂ CHF ₂ OH CH ₃ 2-OCH ₃ 3,5-Cl ₂ -4-O (Q38-3-Cl-5-CF ₃ ) OH CH ₃ 2-OCH ₃ 2,4-F ₂ -3,5-Cl ₂ OH CH ₃ 2-CF ₃ 4-Cl OH CH ₃ 2-CF ₃ 4-Br OH CH ₃ 2-CF ₃ 4-CF ₃ OH CH ₃ 2-CF ₃ 4-OCF ₃ OH CH ₃ 2-CF ₃ 4-OCF ₂ CHF ₂ OH CH ₃ 2-CF ₃ 3-OCF ₂ O-4 OH CH ₃ 2-CF ₃ 4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) OH CH ₃ 2-CF ₃ 4-CH ₂ ON = C (Q51) (C ₆ H ₄ -4-Cl) O ──────── ──────────────────────────

[0062]

[Table 25] ────────────────────────────────── R ¹ R ² X _l Y _m Z ─── ─────────────────────────────── H CH ₃ 2-CF ₃ 4-O (Q38-3-Cl-5- CF ₃ ) OH CH ₃ 2-CF ₃ 3,4-Cl ₂ OH CH ₃ 2-CF ₃ 3,5-Cl ₂ OH CH ₃ 2-CF ₃ 3,4-Br ₂ OH CH ₃ 2-CF ₃ 2 -F-4-Cl OH CH ₃ 2-CF ₃ 2-F-4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) OH CH ₃ 2-CF ₃ 2-F-4-O ( Q38-3-Cl-5-CF ₃ ) OH CH ₃ 2-CF ₃ 3-F-4-Cl OH CH ₃ 2-CF ₃ 3-Cl-4-Br OH CH ₃ 2-CF ₃ 2,5- F ₂ -4-Cl OH CH ₃ 2-CF ₃ 3,4,5-Cl ₃ OH CH ₃ 2-CF ₃ 3,5-Cl ₂ -4-OCF ₂ CHF ₂ OH CH ₃ 2-CF ₃ 3, 5-Cl ₂ -4-O (Q38-3-Cl-5-CF ₃ ) OH CH ₃ 2-CF ₃ 2,4-F ₂ -3,5-Cl ₂ OH CH ₃ 2,4,6-F ₃ 4-Cl OH CH ₃ 2,4,6-F ₃ 4-Br OH CH ₃ 2,4,6-F ₃ 4-CF ₃ OH CH ₃ 2,4,6-F ₃ 4-OCF ₃ OH CH ₃ 2,4,6-F ₃ 4-OCF ₂ CHF ₂ OH CH ₃ 2,4,6-F ₃ 3-OCF ₂ O-4 OH CH ₃ 2,4,6-F ₃ 4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) OH CH ₃ 2,4,6-F ₃ 4-CH ₂ ON = C (Q51) (C ₆ H ₄ -4-Cl) OH CH ₃ 2,4, _{6-F 3 4-O (} Q38-3-Cl-5-CF 3) O ─────── ──────────────────────────

[0063]

[Table 26] ────────────────────────────────── R ¹ R ² X _l Y _m Z ─── ─────────────────────────────── H CH ₃ 2,4,6-F ₃ 3,4-Cl ₂ OH CH ₃ 2,4,6-F ₃ 3,5-Cl ₂ OH CH ₃ 2,4,6-F ₃ 3,4-Br ₂ OH CH ₃ 2,4,6-F ₃ 2-F-4-Cl OH CH ₃ 2,4,6-F ₃ 2-F-4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) OH CH ₃ 2,4,6-F ₃ 2-F-4- O (Q38-3-Cl-5-CF ₃ ) OH CH ₃ 2,4,6-F ₃ 3-F-4-Cl OH CH ₃ 2,4,6-F ₃ 3-Cl-4-Br OH CH ₃ 2,4,6-F ₃ 2,5-F ₂ -4-Cl OH CH ₃ 2,4,6-F ₃ 3,4,5-Cl ₃ OH CH ₃ 2,4,6-F ₃ 3,5-Cl ₂ -4-OCF ₂ CHF ₂ OH CH ₃ 2,4,6-F ₃ 3,5-Cl ₂ -4-O (Q38-3-Cl-5-CF ₃ ) OH CH ₃ 2 , 4,6-F ₃ 2,4-F ₂ -3,5-Cl ₂ OH CH ₃ 2,4-F ₂ 4-Cl OH CH ₃ 2,4-F ₂ 4-Br OH CH ₃ 2,4 -F ₂ 4-CF ₃ OH CH ₃ 2,4-F ₂ 4-OCF ₃ OH CH ₃ 2,4-F ₂ 4-OCF ₂ CHF ₂ OH CH ₃ 2,4-F ₂ 3-OCF ₂ O- 4 OH CH ₃ 2,4-F ₂ 4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) OH CH ₃ 2,4-F ₂ 4-CH ₂ ON = C (Q51) (C ₆ H ₄ -4-Cl) OH CH ₃ 2,4-F ₂ 4-O (Q38-3-Cl-5-CF ₃ ) OH CH ₃ 2,4-F ₂ 3,4-Cl ₂ O ─── ─ ─────────────────────────────

[0064]

[Table 27] ────────────────────────────────── R ¹ R ² X _l Y _m Z ─── ─────────────────────────────── H CH ₃ 2,4-F ₂ 3,5-Cl ₂ OH CH ₃ 2 , 4-F ₂ 3,4-Br ₂ OH CH ₃ 2,4-F ₂ 2-F-4-Cl OH CH ₃ 2,4-F ₂ 2-F-4-O (C ₆ H ₃ -2 -Cl-4-CF ₃ ) OH CH ₃ 2,4-F ₂ 2-F-4-O (Q38-3-Cl-5-CF ₃ ) OH CH ₃ 2,4-F ₂ 3-F-4 -Cl OH CH ₃ 2,4-F ₂ 3-Cl-4-Br OH CH ₃ 2,4-F ₂ 2,5-F ₂ -4-Cl OH CH ₃ 2,4-F ₂ 3,4, 5-Cl ₃ OH CH ₃ 2,4-F ₂ 3,5-Cl ₂ -4-OCF ₂ CHF ₂ OH CH ₃ 2,4-F ₂ 3,5-Cl ₂ -4-O (Q38-3- Cl-5-CF ₃ ) OH CH ₃ 2,4-F ₂ 2,4-F ₂ -3,5-Cl ₂ OH CH ₃ 2-Cl-4-F 4-Cl OH CH ₃ 2-Cl-4 -F 4-Br OH CH ₃ 2-Cl-4-F 4-CF ₃ OH CH ₃ 2-Cl-4-F 4-OCF ₃ OH CH ₃ 2-Cl-4-F 4-OCF ₂ CHF ₂ OH CH ₃ 2-Cl-4-F 3-OCF ₂ O-4 OH CH ₃ 2-Cl-4-F 4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) OH CH ₃ 2-Cl -4-F 4-CH ₂ ON = C (Q51) (C ₆ H ₄ -4-Cl) OH CH ₃ 2-Cl-4-F 4-O (Q38-3-Cl-5-CF ₃ ) OH _{CH 3 2-Cl-4-} F 3,4-Cl 2 OH CH 3 2-Cl-4-F 3,5-Cl 2 O ───────── ────────────────────────

[0065]

[Table 28] ────────────────────────────────── R ¹ R ² X _l Y _m Z ─── ─────────────────────────────── H CH ₃ 2-Cl-4-F 3,4-Br ₂ OH CH ₃ 2-Cl-4-F 2-F-4-Cl OH CH ₃ 2-Cl-4-F 2-F-4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) OH CH ₃ 2 -Cl-4-F 2-F-4-O (Q38-3-Cl-5-CF ₃ ) OH CH ₃ 2-Cl-4-F 3-F-4-Cl OH CH ₃ 2-Cl-4 -F 3-Cl-4-Br OH CH ₃ 2-Cl-4-F 2,5-F ₂ -4-Cl OH CH ₃ 2-Cl-4-F 3,4,5-Cl ₃ OH CH ₃ 2-Cl-4-F 3,5-Cl ₂ -4-OCF ₂ CHF ₂ OH CH ₃ 2-Cl-4-F 3,5-Cl ₂ -4-O (Q38-3-Cl-5-CF ₃ ) OH CH ₃ 2-Cl-4-F 2,4-F ₂ -3,5-Cl ₂ OH CH ₃ 2-I 4-Cl OH CH ₃ 2-I 4-CF ₃ OH CH ₃ 2-I 4-OCF ₃ OH CH ₃ 2-I 4-O (Q38-3-Cl-5-CF ₃ ) OH CH ₃ 2-I 3,4-Cl ₂ OH CH ₃ 2-I 2-F-4-Cl OH CH ₃ 2-I 2-F-4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) OH CH ₃ 2-CH (CH ₃ ) ₂ 4-Cl OH CH ₃ 2-CH (CH ₃ ) ₂ 4-CF ₃ OH CH ₃ 2-CH (CH ₃ ) ₂ 4-OCF ₃ OH CH ₃ 2-CH (CH ₃ ) ₂ 4-O (Q38-3-Cl-5-CF ₃ ) OH CH _{3 2-CH (CH 3)} 2 3,4-Cl 2 O ────────────── ───────────────────

[0066]

[Table 29] ────────────────────────────────── R ¹ R ² X _l Y _m Z ─── ─────────────────────────────── H CH ₃ 2-CH (CH ₃ ) ₂ 2-F-4-Cl OH CH ₃ 2-CH (CH ₃ ) ₂ 2-F-4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) OH CH ₃ 2-CN 4-Cl OH CH ₃ 2-CN 4-CF ₃ OH CH ₃ 2-CN 4-OCF ₃ OH CH ₃ 2-CN 4-O (Q38-3-Cl-5-CF ₃ ) OH CH ₃ 2-CN 3,4-Cl ₂ OH CH ₃ 2-CN 2-F-4-Cl OH CH ₃ 2-CN 2-F-4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) OH CH ₃ 2-NO ₂ 4-Cl OH CH ₃ 2- NO ₂ 4-CF ₃ OH CH ₃ 2-NO ₂ 4-OCF ₃ OH CH ₃ 2-NO ₂ 4-O (Q38-3-Cl-5-CF ₃ ) OH CH ₃ 2-NO ₂ 3,4- Cl ₂ OH CH ₃ 2-NO ₂ 2-F-4-Cl OH CH ₃ 2-NO ₂ 2-F-4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) OH CH ₃ 2, 6-F ₂ -3-NH ₂ 4-Cl OH CH ₃ 2,6-F ₂ -3-NH ₂ 4-CF ₃ OH CH ₃ 2,6-F ₂ -3-NH ₂ 4-OCF ₃ OH CH ₃ 2,6-F ₂ -3-NH ₂ 4-O (Q38-3-Cl-5-CF ₃ ) OH CH ₃ 2,6-F ₂ -3-NH ₂ 3,4-Cl ₂ OH CH ₃ 2,6-F ₂ -3-NH ₂ 2-F-4-Cl OH CH ₃ 2,6-F ₂ -3-NH ₂ 2-F-4-O (C ₆ H ₃ -2-Cl-4 -CF ₃₎ O ──────────── ─────────────────────

[0067]

[Table 30] ────────────────────────────────── R ¹ R ² X _l Y _m Z ─── ─────────────────────────────── H CH ₃ 2-SCH ₃ 4-Cl OH CH ₃ 2-SCH ₃ 4- CF ₃ OH CH ₃ 2-SCH ₃ 4-OCF ₃ OH CH ₃ 2-SCH ₃ 4-O (Q38-3-Cl-5-CF ₃ ) OH CH ₃ 2-SCH ₃ 3,4-Cl ₂ OH CH ₃ 2-SCH ₃ 2-F-4-Cl OH CH ₃ 2-SCH ₃ 2-F-4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) OH CH ₃ 2-OCHF ₂ 4- Cl OH CH ₃ 2-OCHF ₂ 4-CF ₃ OH CH ₃ 2-OCHF ₂ 4-OCF ₃ OH CH ₃ 2-OCHF ₂ 4-O (Q38-3-Cl-5-CF ₃ ) OH CH ₃ 2- OCHF ₂ 3,4-Cl ₂ OH CH ₃ 2-OCHF ₂ 2-F-4-Cl OH CH ₃ 2-OCHF ₂ 2-F-4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) OH CH ₃ 2-OCF ₃ 4-Cl OH CH ₃ 2-OCF ₃ 4-CF ₃ OH CH ₃ 2-OCF ₃ 4-OCF ₃ OH CH ₃ 2-OCF ₃ 4-O (Q38-3-Cl- 5-CF ₃ ) OH CH ₃ 2-OCF ₃ 3,4-Cl ₂ OH CH ₃ 2-OCF ₃ 2-F-4-Cl OH CH ₃ 2-OCF ₃ 2-F-4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) OH CH ₃ 2-SCF ₃ 4-Cl OH CH ₃ 2-SCF ₃ 4-CF ₃ O ────────────────── ──────────────── ─

[0068]

[Table 31] ────────────────────────────────── R ¹ R ² X _l Y _m Z ─── ─────────────────────────────── H CH ₃ 2-SCF ₃ 4-OCF ₃ OH CH ₃ 2-SCF ₃ 4 -O (Q38-3-Cl-5-CF ₃ ) OH CH ₃ 2-SCF ₃ 3,4-Cl ₂ OH CH ₃ 2-SCF ₃ 2-F-4-Cl OH CH ₃ 2-SCF ₃ 2- F-4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) OH CH ₃ 2-Br-6-F 4-Cl OH CH ₃ 2-Br-6-F 4-CF ₃ OH CH ₃ 2-Br-6-F 4-OCF ₃ OH CH ₃ 2-Br-6-F 4-O (Q38-3-Cl-5-CF ₃ ) OH CH ₃ 2-Br-6-F 3,4- Cl ₂ OH CH ₃ 2-Br-6-F 2-F-4-Cl OH CH ₃ 2-Br-6-F 2-F-4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) OH CH ₃ 2,3,6-F ₃ 4-Cl OH CH ₃ 2,3,6-F ₃ 4-CF ₃ OH CH ₃ 2,3,6-F ₃ 4-OCF ₃ OH CH ₃ 2, 3,6-F ₃ 4-O (Q38-3-Cl-5-CF ₃ ) OH CH ₃ 2,3,6-F ₃ 3,4-Cl ₂ OH CH ₃ 2,3,6-F ₃ 2 -F-4-Cl OH CH ₃ 2,3,6-F ₃ 2-F-4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) OH CH ₃ 2,4-F ₂ -6 -Cl 4-Cl OH CH ₃ 2,4-F ₂ -6-Cl 4-CF ₃ OH CH ₃ 2,4-F ₂ -6-Cl 4-OCF ₃ OH CH ₃ 2,4-F ₂ -6 -Cl 4-O (Q38-3-Cl -5-CF 3) O ────────────── ───────────────────

[0069]

[Table 32] ────────────────────────────────── R ¹ R ² X _l Y _m Z ─── ─────────────────────────────── H CH ₃ 2,4-F ₂ -6-Cl 3,4-Cl ₂ OH CH ₃ 2,4-F ₂ -6-Cl 2-F-4-Cl OH CH ₃ 2,4-F ₂ -6-Cl 2-F-4-O (C ₆ H ₃ -2-Cl- 4-CF ₃ ) OH CH ₃ 2,5-F ₂ 4-Cl OH CH ₃ 2,5-F ₂ 4-CF ₃ OH CH ₃ 2,5-F ₂ 4-OCF ₃ OH CH ₃ 2,5- F ₂ 4-O (Q38-3-Cl-5-CF ₃ ) OH CH ₃ 2,5-F ₂ 3,4-Cl ₂ OH CH ₃ 2,5-F ₂ 2-F-4-Cl OH CH ₃ 2,5-F ₂ 2-F-4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) OH CH ₃ 2,6- (OCH ₃ ) ₂ 4-Cl OH CH ₃ 2,6 -(OCH ₃ ) ₂ 4-CF ₃ OH CH ₃ 2,6- (OCH ₃ ) ₂ 4-OCF ₃ OH CH ₃ 2,6- (OCH ₃ ) ₂ 4-O (Q38-3-Cl-5- CF ₃ ) OH CH ₃ 2,6- (OCH ₃ ) ₂ 3,4-Cl ₂ OH CH ₃ 2,6- (OCH ₃ ) ₂ 2-F-4-Cl OH CH ₃ 2,6- (OCH ₃ ) ₂ 2-F-4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) OH CH ₃ 2,4-Cl ₂ 4-Cl OH CH ₃ 2,4-Cl ₂ 4-CF ₃ OH CH ₃ 2,4-Cl ₂ 4-OCF ₃ OH CH ₃ 2,4-Cl ₂ 4-O (Q38-3-Cl-5-CF ₃ ) OH CH ₃ 2,4-Cl ₂ 3,4-Cl ₂ OH CH ₃ 2,4-Cl ₂ 2-F-4-Cl O ───────── ─────────────────────────

[0070]

[Table 33] ────────────────────────────────── R ¹ R ² X _l Y _m Z ─── ─────────────────────────────── H CH ₃ 2,4-Cl ₂ 2-F-4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) OHH 2-F 4-Cl OHH 2-F 4-Br OHH 2-F 4-CF ₃ OHH 2-F 4-OCF ₃ OHH 2-F 4-OCF ₂ CHF ₂ OHH 2-F 3-OCF ₂ O-4 OHH 2-F 4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) OHH 2-F 4-CH ₂ ON = C (Q51) ( C ₆ H ₄ -4-Cl) OHH 2-F 4-O (Q38-3-Cl-5-CF ₃ ) OHH 2-F 3,4-Cl ₂ OHH 2-F 3,5-Cl ₂ OHH 2 -F 3,4-Br ₂ OHH 2-F 2-F-4-Cl OHH 2-F 2-F-4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) OHH 2-F 2 -F-4-O (Q38-3-Cl-5-CF ₃ ) OHH 2-F 3-F-4-Cl OHH 2-F 3-Cl-4-Br OHH 2-F 2,5-F ₂ -4-Cl OHH 2-F 3,4,5-Cl ₃ OHH 2-F 3,5-Cl ₂ -4-OCF ₂ CHF ₂ OHH 2-F 3,5-Cl ₂ -4-O (Q38- 3-Cl-5-CF ₃ ) OHH 2-F 2,4-F ₂ -3,5-Cl ₂ O ──────────────────────── ───────────

[0071]

[Table 34] ────────────────────────────────── R ¹ R ² X _l Y _m Z ─── ─────────────────────────────── H CH ₃ 2-Cl 4-Cl SH CH ₃ 2-F 4-Br SH CH ₃ 2-Cl 4-CF ₃ SH CH ₃ 2-F 4-OCF ₃ SH CH ₃ 2-Cl 4-OCF ₂ CHF ₂ SH CH ₃ 2-F 3-OCF ₂ O-4 SH CH ₃ 2-Cl 4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) SH CH ₃ 2-F 4-CH ₂ ON = C (Q51) (C ₆ H ₄ -4-Cl) SH CH ₃ 2-Cl 4-O (Q38-3-Cl-5-CF ₃ ) SH CH ₃ 2-F 3,4-Cl ₂ SH CH ₃ 2-Cl 3,5-Cl ₂ SH CH ₃ 2-F 3,4-Br ₂ SH CH ₃ 2-Cl 2-F-4-Cl SH CH ₃ 2-F 2-F-4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) SH CH ₃ 2-Cl 2- F-4-O (Q38-3-Cl-5-CF ₃ ) SH CH ₃ 2-F 3-F-4-Cl SH CH ₃ 2-Cl 3-Cl-4-Br SH CH ₃ 2-F 2 , 5-F ₂ -4-Cl SH CH ₃ 2-Cl 3,4,5-Cl ₃ SH CH ₃ 2-F 3,5-Cl ₂ -4-OCF ₂ CHF ₂ SH CH ₃ 2-Cl 3, 5-Cl ₂ -4-O (Q38-3-Cl-5-CF ₃ ) SH CH ₃ 2-F 2,4-F ₂ -3,5-Cl ₂ SH CH ₂ CH ₃ 2-Cl 4-Cl O ──────────────────────────────────

[0072]

[Table 35] ────────────────────────────────── R ¹ R ² X _l Y _m Z ─── ─────────────────────────────── H CH ₂ CH ₃ 2-F 4-Br OH CH ₂ CH ₃ 2-Cl 4-CF ₃ OH CH ₂ CH ₃ 2-F 4-OCF ₃ OH CH ₂ CH ₃ 2-Cl 4-OCF ₂ CHF ₂ OH CH ₂ CH ₃ 2-F 3-OCF ₂ O-4 OH CH ₂ CH ₃ 2-Cl 4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) OH CH ₂ CH ₃ 2-F 4-CH ₂ ON = C (Q51) (C ₆ H ₄ -4-Cl) OH CH ₂ CH ₃ 2-Cl 4-O (Q38-3-Cl-5-CF ₃ ) OH CH ₂ CH ₃ 2-F 3,4-Cl ₂ OH CH ₂ CH ₃ 2-Cl 3,5-Cl ₂ OH CH ₂ CH ₃ 2-F 3,4-Br ₂ OH CH ₂ CH ₃ 2-Cl 2-F-4-Cl OH CH ₂ CH ₃ 2-F 2-F-4-O (C ₆ H _3- 2-Cl-4-CF ₃ ) OH CH ₂ CH ₃ 2-Cl 2-F-4-O (Q38-3-Cl-5-CF ₃ ) OH CH ₂ CH ₃ 2-F 3-F-4- Cl OH CH ₂ CH ₃ 2-Cl 3-Cl-4-Br OH CH ₂ CH ₃ 2-F 2,5-F ₂ -4-Cl OH CH ₂ CH ₃ 2-Cl 3,4,5-Cl ₃ OH CH ₂ CH ₃ 2-F 3,5-Cl ₂ -4-OCF ₂ CHF ₂ OH CH ₂ CH ₃ 2-Cl 3,5-Cl ₂ -4-O (Q38-3-Cl-5-CF ₃ ) OH CH ₂ CH ₃ 2-F 2,4-F ₂ -3,5-Cl ₂ OH CH ₃ 2-Cl 4-OCF ₃ NH H CH ₃ 2-F 4-O (Q38-3-Cl-5 -CF ₃ ) NH ──────────────────────────────────

[0073]

[Table 36] ────────────────────────────────── R ¹ R ² X _l Y _m Z ─── ─────────────────────────────── H CH ₃ 2-Cl 3,4-Cl ₂ NH H CH ₃ 2-F 2-F-4-Cl NH H CH ₃ 2-Cl 2-F-4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) NH H CH ₃ 2-F 4-Cl NH H CH ₃ 2-Cl 4-CF ₃ NH H CH ₂ CH ₂ CH ₃ 2-F 4-OCF ₃ OH CH ₂ CH ₂ CH ₃ 2-Cl 4-O (Q38-3-Cl-5-CF ₃ ) OH CH ₂ CH ₂ CH ₃ 2-F 3,4-Cl ₂ OH CH ₂ CH ₂ CH ₃ 2-Cl 2-F-4-Cl OH CH ₂ CH ₂ CH ₃ 2-F 2-F-4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) OH CH ₂ CH ₂ CH ₃ 2-Cl 4-Cl OH CH ₂ CH ₂ CH ₃ 2-F 4-CF ₃ O CH ₃ CH ₃ 2-Cl 4-OCF ₃ O CH ₃ CH ₃ 2-F 4-O (Q38-3-Cl-5-CF ₃ ) O CH ₃ CH ₃ 2-Cl 3,4-Cl ₂ O CH ₃ CH ₃ 2-F 2-F- 4-Cl O CH ₃ CH ₃ 2-Cl 2-F-4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) O CH ₃ CH ₃ 2-F 4-Cl O CH ₃ CH ₃ 2 -Cl 4-CF ₃ O CH ₂ CH ₃ CH ₃ 2-F 4-OCF ₃ O CH ₂ CH ₃ CH ₃ 2-Cl 4-O (Q38-3-Cl-5-CF ₃ ) O CH ₂ CH ₃ CH ₃ 2-F 3,4-Cl ₂ O CH ₂ CH ₃ CH ₃ 2-Cl 2-F-4-Cl O ───────────── ──────────────────────

[0074]

[Table 37] ────────────────────────────────── R ¹ R ² X _l Y _m Z ─── ─────────────────────────────── CH ₂ CH ₃ CH ₃ 2-F 2-F-4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) O CH ₂ CH ₃ CH ₃ 2-Cl 4-Cl O CH ₂ CH ₃ CH ₃ 2-F 4-CF ₃ O CH (CH ₃ ) ₂ CH ₃ 2- Cl 4-OCF ₃ O CH (CH ₃ ) ₂ CH ₃ 2-F 4-O (Q38-3-Cl-5-CF ₃ ) O CH (CH ₃ ) ₂ CH ₃ 2-Cl 3,4-Cl ₂ O CH (CH ₃ ) ₂ CH ₃ 2-F 2-F-4-Cl O CH (CH ₃ ) ₂ CH ₃ 2-Cl 2-F-4-O (C ₆ H ₃ -2-Cl-4- CF ₃ ) O CH (CH ₃ ) ₂ CH ₃ 2-F 4-Cl O CH (CH ₃ ) ₂ CH ₃ 2-Cl 4-CF ₃ OC (CH ₃ ) ₃ CH ₃ 2-F 4-OCF ₃ OC (CH ₃ ) ₃ CH ₃ 2-Cl 4-O (Q38-3-Cl-5-CF ₃ ) OC (CH ₃ ) ₃ CH ₃ 2-F 3,4-Cl ₂ OC (CH ₃ ) ₃ CH ₃ 2-Cl 2-F-4-Cl OC (CH ₃ ) ₃ CH ₃ 2-F 2-F-4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) OC (CH ₃ ) ₃ CH ₃ 2-Cl 4-Cl OC (CH ₃ ) ₃ CH ₃ 2-F 4-CF ₃ O CH ₂ CH = CH ₂ CH ₃ 2-Cl 4-OCF ₃ O CH ₂ CH = CH ₂ CH ₃ 2-F 4-O (Q38-3-Cl-5-CF ₃ ) O CH ₂ CH = CH ₂ CH ₃ 2-Cl 3,4-Cl ₂ O CH ₂ CH = CH ₂ CH ₃ 2-F 2-F-4 -Cl O CH ₂ CH = CH ₂ CH ₃ 2-Cl 2-F-4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) O CH ₂ CH = CH ₂ CH ₃ 2-F 4-Cl O ────── ────────────────────────────

[0075]

[Table 38] ────────────────────────────────── R ¹ R ² X _l Y _m Z ─── ─────────────────────────────── CH ₂ CH = CH ₂ CH ₃ 2-Cl 4-CF ₃ O CH ₂ C ≡ CH CH ₃ 2-F 4-OCF ₃ O CH ₂ C ≡ CH CH ₃ 2-Cl 4-O (Q38-3-Cl-5-CF ₃ ) O CH ₂ C ≡ CH CH ₃ 2-F 3, 4-Cl ₂ O CH ₂ C ≡ CH CH ₃ 2-Cl 2-F-4-Cl O CH ₂ C ≡ CH CH ₃ 2-F 2-F-4-O (C ₆ H ₃ -2-Cl- 4-CF ₃ ) O CH ₂ C≡CH CH ₃ 2-Cl 4-Cl O CH ₂ C≡CH CH ₃ 2-F 4-CF ₃ O CHF ₂ CH ₃ 2-Cl 4-OCF ₃ O CHF ₂ CH ₃ 2-F 4-O (Q38-3-Cl-5-CF ₃ ) O CHF ₂ CH ₃ 2-Cl 3,4-Cl ₂ O CHF ₂ CH ₃ 2-F 2-F-4-Cl O CHF ₂ CH ₃ 2-Cl 2-F-4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) O CHF ₂ CH ₃ 2-F 4-Cl O CHF ₂ CH ₃ 2-Cl 4-CF ₃ O CF ₃ CH ₃ 2-F 4-OCF ₃ O CF ₃ CH ₃ 2-Cl 4-O (Q38-3-Cl-5-CF ₃ ) O CF ₃ CH ₃ 2-F 3,4-Cl ₂ O CF ₃ CH ₃ 2-F 2-F-4-Cl O CF ₃ CH ₃ 2-Cl 2-F-4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) O CF ₃ CH ₃ 2-F 4-Cl O CF ₃ CH ₃ 2-Cl 4-CF ₃ O CH ₂ OCH ₃ CH ₃ 2-F 4-OCF ₃ O ─── ───────────────────────────────

[0076]

[Table 39] ────────────────────────────────── R ¹ R ² X _l Y _m Z ─── ─────────────────────────────── CH ₂ OCH ₃ CH ₃ 2-Cl 4-O (Q38-3-Cl- 5-CF ₃ ) O CH ₂ OCH ₃ CH ₃ 2-F 3,4-Cl ₂ O CH ₂ OCH ₃ CH ₃ 2-F 2-F-4-Cl O CH ₂ OCH ₃ CH ₃ 2-Cl 2- F-4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) O CH ₂ OCH ₃ CH ₃ 2-F 4-Cl O CH ₂ OCH ₃ CH ₃ 2-Cl 4-CF ₃ O CH ₂ OCH ₂ CH ₃ CH ₃ 2-F 4-OCF ₃ O CH ₂ OCH ₂ CH ₃ CH ₃ 2-Cl 4-O (Q38-3-Cl-5-CF ₃ ) O CH ₂ OCH ₂ CH ₃ CH ₃ 2 -F 3,4-Cl ₂ O CH ₂ OCH ₂ CH ₃ CH ₃ 2-F 2-F-4-Cl O CH ₂ OCH ₂ CH ₃ CH ₃ 2-Cl 2-F-4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) O CH ₂ OCH ₂ CH ₃ CH ₃ 2-F 4-Cl O CH ₂ OCH ₂ CH ₃ CH ₃ 2-Cl 4-CF ₃ O CHO CH ₃ 2-F 4 -OCF ₃ O CHO CH ₃ 2-Cl 4-O (Q38-3-Cl-5-CF ₃ ) O CHO CH ₃ 2-F 3,4-Cl ₂ O CHO CH ₃ 2-F 2-F-4 -Cl O CHO CH ₃ 2-Cl 2-F-4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) O CHO CH ₃ 2-F 4-Cl O CHO CH ₃ 2-Cl 4- CF ₃ O COCH ₃ CH ₃ 2-F 4-OCF ₃ O COCH ₃ CH ₃ 2-Cl 4-O (Q38-3-Cl-5-CF ₃ ) O COCH ₃ CH ₃ 2-F 3,4-Cl ₂ O ────────────────────────────────── ─

[0077]

[Table 40] ────────────────────────────────── R ¹ R ² X _l Y _m Z ─── ─────────────────────────────── COCH ₃ CH ₃ 2-F 2-F-4-Cl O COCH ₃ CH ₃ 2-Cl 2-F-4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) O COCH ₃ CH ₃ 2-F 4-Cl O COCH ₃ CH ₃ 2-Cl 4-CF ₃ O CO ₂ CH ₂ CH ₃ CH ₃ 2-F 4-OCF ₃ O CO ₂ CH ₂ CH ₃ CH ₃ 2-Cl 4-O (Q38-3-Cl-5-CF ₃ ) O CO ₂ CH ₂ CH ₃ CH ₃ 2-F 3,4-Cl ₂ O CO ₂ CH ₂ CH ₃ CH ₃ 2-F 2-F-4-Cl O CO ₂ CH ₂ CH ₃ CH ₃ 2-Cl 2-F-4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) O CO ₂ CH ₂ CH ₃ CH ₃ 2-F 4-Cl O CO ₂ CH ₂ CH ₃ CH ₃ 2-Cl 4-CF ₃ O CO ₂ C (CH ₃ ) ₃ CH ₃ 2-F 4-OCF ₃ O CO ₂ C (CH ₃ ) ₃ CH ₃ 2-Cl 4-O (Q38-3-Cl-5-CF ₃ ) O CO ₂ C (CH ₃ ) ₃ CH ₃ 2-F 3,4-Cl ₂ O CO ₂ C (CH ₃ ) ₃ CH ₃ 2-F 2-F-4-Cl O CO ₂ C (CH ₃ ) ₃ CH ₃ 2-Cl 2-F-4 -O (C ₆ H ₃ -2-Cl-4-CF ₃ ) O CO ₂ C (CH ₃ ) ₃ CH ₃ 2-F 4-Cl O CN CH ₃ 2-Cl 4-CF ₃ O CN CH ₃ 2 -F 4-OCF ₃ O CN CH ₃ 2-Cl 4-O (Q38-3-Cl-5-CF ₃ ) O CN CH ₃ 2-F 3,4-Cl ₂ O CN CH ₃ 2-F 2-F-4-Cl O CN CH ₃ 2-Cl 2-F-4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) O ────────── ─────────────────────────

[0078]

[Table 41] ────────────────────────────────── R ¹ R ² X _l Y _m Z ─── ─────────────────────────────── CN CH ₃ 2-F 4-Cl O CH ₂ CN CH ₃ 2-Cl 4 -CF ₃ O CH ₂ CN CH ₃ 2-F 4-OCF ₃ O CH ₂ CN CH ₃ 2-Cl 4-O (Q38-3-Cl-5-CF ₃ ) O CH ₂ CN CH ₃ 2-F 3 , 4-Cl ₂ O CH ₂ CN CH ₃ 2-F 2-F-4-Cl O CH ₂ CN CH ₃ 2-Cl 2-F-4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) O CH ₂ CN CH ₃ 2-F 4-Cl O CH ₂ CO ₂ CH ₃ CH ₃ 2-Cl 4-CF ₃ O CH ₂ CO ₂ CH ₃ CH ₃ 2-F 4-OCF ₃ O CH ₂ CO ₂ CH ₃ CH ₃ 2-Cl 4-O (Q38-3-Cl-5-CF ₃ ) O CH ₂ CO ₂ CH ₃ CH ₃ 2-F 3,4-Cl ₂ O CH ₂ CO ₂ CH ₃ CH ₃ 2-F 2-F-4-Cl O CH ₂ CO ₂ CH ₃ CH ₃ 2-Cl 2-F-4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) O CH ₂ CO ₂ CH ₃ CH ₃ 2-F 4-Cl O NH ₂ CH ₃ 2-Cl 4-CF ₃ O NH ₂ CH ₃ 2-F 4-OCF ₃ O NH ₂ CH ₃ 2-Cl 4-O (Q38-3-Cl -5-CF ₃ ) O NH ₂ CH ₃ 2-F 3,4-Cl ₂ O NH ₂ CH ₃ 2-F 2-F-4-Cl O NH ₂ CH ₃ 2-Cl 2-F-4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) O NH ₂ CH ₃ 2-F 4-Cl O COCO ₂ CH ₂ CH ₃ CH ₃ 2-Cl 4-CF ₃ O ──────────────────────────────────

[0079]

[Table 42] ────────────────────────────────── R ¹ R ² X _l Y _m Z ─── ─────────────────────────────── COCO ₂ CH ₂ CH ₃ CH ₃ 2-F 4-OCF ₃ O COCO ₂ CH ₂ CH ₃ CH ₃ 2-Cl 4-O (Q38-3-Cl-5-CF ₃ ) O COCO ₂ CH ₂ CH ₃ CH ₃ 2-F 3,4-Cl ₂ O COCO ₂ CH ₂ CH ₃ CH ₃ 2-F 2-F-4-Cl O COCO ₂ CH ₂ CH ₃ CH ₃ 2-Cl 2-F-4-O (C ₆ H ₃ -2-Cl-4-CF ₃ ) O COCO ₂ CH ₂ CH ₃ CH ₃ 2-F 4-Cl O SCCl ₃ CH ₃ 2-Cl 4-CF ₃ O SC ₆ H ₅ CH ₃ 2-F 4-OCF ₃ OS (C ₆ H ₄ -2-CH ₃ ) CH ₃ 2 -Cl 4-O (Q38-3-Cl-5-CF ₃ ) OS (C ₆ H ₄ -3-CH ₃ ) CH ₃ 2-F 3,4-Cl ₂ OS (C ₆ H ₄ -4-CH ₃ ) CH ₃ 2-F 2-F-4-Cl OS (C ₆ H ₄ -4-Cl) CH ₃ 2-F 4-Cl OS (C ₆ H ₄ -4-Br) CH ₃ 2-Cl 4 -CF ₃ OS (C ₆ H ₄ -4-NO ₂ ) CH ₃ 2-F 4-OCF ₃ OS (C ₆ H ₄ -2-CO ₂ CH ₃ ) CH ₃ 2-F 4-Cl OS (C ₆ H ₃ -2,4- (NO ₂ ) ₂ CH ₃ 2-Cl 4-CF ₃ O SN (CH ₃ ) CH ₂ CH ₂ CH ₃ CH ₃ 2-F 4-OCF ₃ O SN (CH ₂ CH ₂ CH ₂ CH ₃ ) ₂ CH ₃ 2-Cl 4-O (Q38-3-Cl-5-CF ₃ ) O SN (CH ₃ ) CO ₂ CH ₂ CH ₃ CH ₃ 2-F 3,4-Cl ₂ O SN (CH ₃ ) CO ₂ CH (CH ₃ ) ₂ CH ₃ 2-F 2-F-4-Cl O SN (CH ₂ CH ₃ ) CO ₂ CH ₃ CH ₃ 2 -F 4-Cl O SN (CH (CH ₃ ) ₂ ) CO ₂ CH ₃ CH ₃ 2-Cl 4-CF ₃ O SN (CH ₂ CH ₂ CH ₃ ) CO ₂ CH ₃ CH ₃ 2-F 4-OCF ₃ O ──────────────────────────────────

[0080]

[Table 43] ────────────────────────────────── R ¹ R ² X _l Y _m Z ─── ─────────────────────────────── SN (CH ₃ ) CH ₂ CH ₂ CO ₂ CH ₃ CH ₃ 2-Cl 4 -O (Q38-3-Cl-5-CF ₃ ) O Na CH ₃ 2-F 3,4-Cl ₂ O Na CH ₃ 2-F 2-F-4-Cl OK CH ₃ 2-F 4-Cl OK CH ₃ 2-Cl 4-CF ₃ O Ca CH ₃ 2-F 4-OCF ₃ O Ca CH ₃ 2-F 2-F-4-Cl OH CH (CH ₃ ) ₂ 2-F 4-Cl OH CH (CH ₃ ) ₂ 2-Cl 4-CF ₃ OH CH (CH ₃ ) ₂ 2-F 4-OCF ₃ OH CH (CH ₃ ) ₂ 2-Cl 4-O (Q38-3-Cl-5-CF ₃ ) OH CH (CH ₃ ) ₂ 2-F 3,4-Cl ₂ OH CH (CH ₃ ) ₂ 2-F 2-F-4-Cl OH CH ₂ CH ₂ CH ₂ CH ₃ 2-F 4-Cl OH CH ₂ CH ₂ CH ₂ CH ₃ 2-Cl 4-CF ₃ OH CH ₂ CH ₂ CH ₂ CH ₃ 2-F 4-OCF ₃ OH CH ₂ CH ₂ CH ₂ CH ₃ 2-Cl 4-O (Q38-3 -Cl-5-CF ₃ ) OH CH ₂ CH ₂ CH ₂ CH ₃ 2-F 3,4-Cl ₂ OH CH ₂ CH ₂ CH ₂ CH ₃ 2-F 2-F-4-Cl OHC (CH ₃ ) ₃ 2-F 4-Cl OHC (CH ₃ ) ₃ 2-Cl 4-CF ₃ OHC (CH ₃ ) ₃ 2-F 4-OCF ₃ OHC (CH ₃ ) ₃ 2-Cl 4-O (Q38-3- Cl-5-CF ₃ ) O ─────────────────── ───────────────

[0081]

[Table 44] ────────────────────────────────── R ¹ R ² X _l Y _m Z ─── ─────────────────────────────── HC (CH ₃ ) ₃ 2-F 3,4-Cl ₂ OHC (CH ₃ ) ₃ 2-F 2-F-4-Cl OH CH ₂ CH = CH ₂ 2-F 4-Cl OH CH ₂ C ≡ CH 2-Cl 4-CF ₃ OH Q51 2-F 4-OCF ₃ OH Q52 2 -F 2-F-4-Cl OH Q53 2-F 4-Cl OH Q54 2-Cl 4-CF ₃ OH CHF ₂ 2-F 4-OCF ₃ OH CH ₂ Cl 2-Cl 4-O (Q38-3 -Cl-5-CF ₃ ) OH CF ₃ 2-F 3,4-Cl ₂ OH CH = C (Cl) CF ₃ 2-F 2-F-4-Cl OH CH ₂ C≡CBr 2-F 4- Cl OH (Q54-1-Cl) 2-Cl 4-CF ₃ OH (CH ₂ ) ₅ CH ₃ 2-F 4-OCF ₃ OH CH ₂ OCH ₃ 2-Cl 4-O (Q38-3-Cl-5 -CF ₃ ) OH CH ₂ CH ₂ OCH ₃ 2-F 3,4-Cl ₂ OHC ₆ H ₅ 2-F 2-F-4-Cl OH (C ₆ H ₄ -4-Cl) 2-F 4- Cl OH (C ₆ H ₄ -4-CF ₃ ) 2-Cl 4-CF ₃ OH (C ₆ H ₄ -4-OCF ₃ ) 2-F 4-OCF ₃ OH (C ₆ H ₃ -3,4- Cl ₂ ) 2-Cl 4-O (Q38-3-Cl-5-CF ₃ ) OH (C ₆ H ₃ -2-F-4-Cl) 2-F 3,4-Cl ₂ O ──── ──────────────────────────────

[0082]

[Table 45] ────────────────────────────────── R ¹ R ² X _l Y _m Z ─── ─────────────────────────────── H (C ₆ H ₄ -4-SCF ₃ ) 2-F 2-F- 4-Cl O ──────────────────────────────────

In the present invention, the pest controlling agent means especially a pest controlling agent. The compounds of the present invention are effective against various harmful pests at extremely low drug concentrations. Examples of the pest include agricultural pests such as green leafhoppers, brown planthoppers, green peach aphids, mosquitosus alba, Echinochloea lucidum, Kobnomeiga, and Koga moth, spider mites, mandarin mites, kanzawa mites, etc.
Flea, sanitary pests such as lice, weevil, stag beetle, stored grain pests such as striped moth, house pests such as termites, livestock pests such as mites, fleas, lice, indoor dust mites such as mites, leopard mites, tick mites, Examples include molluscs such as slugs and snails. That is, the compound of the present invention, Orthoptera, hemiptera, Lepidoptera, Coleoptera,
It can effectively control pests of Hymenoptera, Diptera, Termites, and mites and lice at low concentrations. On the other hand, it was found that the compound of the present invention is a very useful compound having almost no adverse effect on mammals, fish, crustaceans and beneficial insects, and completed the present invention.

Next, a method for producing the compound of the present invention will be described. The compound of the present invention is a novel imidazolinone derivative, and a typical production method thereof will be specifically described below.

In each method (method A to method F), R ¹ ,
R ² , X, Y, Z, l and m have the same meanings as described above,
L represents a good leaving group such as chlorine atom, bromine atom, iodine atom, alkyl sulfonate group or aryl sulfonate group.

[0086]

[Chemical 11]

This method is a method for producing a compound (III) in which R ¹ of the compound (I) of the present invention is a hydrogen atom. Compound (II)
Is reacted with a base in an inert solvent, or is reacted with phosphorus pentachloride in the presence or absence of an inert solvent to give the compound (III) of the present invention. Examples of the base used include alkali metal alkoxides such as sodium ethoxide and potassium tert-butoxide, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, alkali metal carbonates such as sodium carbonate, potassium carbonate and sodium hydrogen carbonate. Examples thereof include salts, alkali metal hydrides such as sodium hydride, and kaurim hydride. The solvent used at this time is methanol,
Lower alcohols such as ethanol, aromatic hydrocarbons such as benzene and toluene, ethers such as diethyl ether, tetrahydrofuran and 1,4-dioxane, amides such as dimethylformamide and dimethylacetamide,
Acetone, acetonitrile, dimethyl sulfoxide, water, etc. are mentioned. These inert solvents may be used alone or in a mixture. Generally, sodium hydride is used as the base and reacted in toluene, or sodium hydroxide is used as the base,
It is preferable to react in a mixed solvent of dioxane and water. The amount of the base used is preferably equivalent to 5 equivalents relative to compound (II). The reaction temperature can be set to any temperature from −80 ° C. to the reflux temperature of the reaction mixture, but it is preferably carried out from room temperature to the reflux temperature. Next, solvents used in the reaction with phosphorus pentachloride include aromatic hydrocarbons such as benzene and toluene, ethers such as diethyl ether and tetrahydrofuran, halogenated hydrocarbons such as chloroform and 1,2-dichloroethane, and oxy. Phosphorus chloride may be mentioned. Generally, it is preferable to use one to two equivalents of phosphorus pentachloride, and to carry out the reaction in toluene or phosphorus oxychloride. Reaction temperature is -80
Although any temperature from 0 ° C to the reflux temperature of the reaction mixture can be set, it is preferably carried out from 0 ° C to the reflux temperature.

[0088]

[Chemical 12]

This method is a method for producing a compound (V) in which R ¹ of the compound (I) of the present invention is a hydrogen atom. The compound (IV) of the present invention is obtained by reacting the compound (IV) with a base and a peroxide in an inert solvent. Examples of the base used include alkali metal alkoxides such as sodium ethoxide and potassium tert-butoxide, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide. Examples of the peroxide used include hydrogen peroxide, peracetic acid, metachloroperbenzoic acid and the like.
Examples of the solvent used include lower alcohols such as methanol and ethanol, aromatic hydrocarbons such as benzene and toluene, halogenated hydrocarbons such as dichloromethane and 1,2-dichloroethane, and water. These inert solvents may be used alone or in a mixture. Generally, it is preferable to use sodium hydroxide as a base and hydrogen peroxide solution as a peroxide, and to carry out the reaction in a mixed solvent of ethanol and water. The reaction temperature can be set to any temperature from −80 ° C. to the reflux temperature of the reaction mixture, but is preferably 0 ° C. to the reflux temperature.

[0090]

[Chemical 13]

This method is a manufacturing method in which R ¹ is other than a hydrogen atom. The compound (I) of the present invention can be obtained by reacting the compound (III) of the present invention with the compound (VI) in the presence of a base in an inert solvent. In the present invention, examples of the base used include alkali metal alkoxides such as sodium ethoxide and potassium tert-butoxide, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, sodium carbonate, potassium carbonate and sodium hydrogen carbonate. Examples thereof include alkali metal carbonates, alkali metal hydrides such as sodium hydride and kaurim hydride, and organic bases such as triethylamine and pyridine. Any solvent may be used as long as it does not inhibit the progress of the reaction, and examples thereof include lower alcohols such as methanol and ethanol, aromatic hydrocarbons such as benzene and toluene, diethyl ether, 1,2-dimethoxyethane, and tetrahydrofuran. , Ethers such as 1,4-dioxane, halogenated hydrocarbons such as dichloromethane and 1,2-dichloroethane, amides such as dimethylformamide and dimethylacetamide, acetonitrile, dimethylsulfoxide and water. These inert solvents may be used alone or in a mixture. Generally, it is preferable to use sodium hydride, potassium hydride, potassium tert-butoxide or potassium hydroxide as a base in a polar solvent such as tetrahydrofuran or dimethylformamide.
The reaction temperature can be set to any temperature from -60 ° C to the reflux temperature of the reaction mixture, but is preferably 0 ° C to 90 ° C.

[0092]

Embedded image

The starting material (II) can be obtained by reacting the compound (VII) with the compound (VIII) in the presence or absence of a base in an inert solvent. Examples of the base used in this reaction include alkali metal alkoxides such as sodium ethoxide and potassium tert-butoxide, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, sodium carbonate, potassium carbonate and sodium hydrogen carbonate. Examples thereof include alkali metal carbonates, alkali metal hydrides such as sodium hydride and kaurim hydride, and organic bases such as triethylamine and pyridine.
The solvent used may be one that does not hinder the progress of the reaction, for example, lower alcohols such as methanol and ethanol, aromatic hydrocarbons such as benzene and toluene, ethers such as diethyl ether and tetrahydrofuran, acetone, Examples thereof include ketones such as methyl ethyl ketone, amides such as dimethylformamide and dimethylacetamide, acetonitrile, dimethyl sulfoxide and water. These inert solvents may be used alone or in a mixture. Generally, it is preferable to use an organic base such as triethylamine or pyridine as a base in a solvent such as tetrahydrofuran, acetone or benzene. The reaction temperature can be set to any temperature from −80 ° C. to the reflux temperature of the reaction mixture, but is preferably 0 ° C. to the reflux temperature.

[0094]

[Chemical 15]

The starting material (IX) in which Z is an oxygen atom can be obtained by hydrolyzing the compound (IV) in the presence of an acid in the presence or absence of an inert solvent. Examples of the acid used include mineral acids such as sulfuric acid and hydrochloric acid. Examples of the solvent used include aromatic hydrocarbons such as benzene and toluene, halogenated hydrocarbons such as dichloromethane and 1,2-dichloroethane, ethers such as diethyl ether and tetrahydrofuran, and water. Generally, concentrated sulfuric acid is used as the acid, and it is preferably carried out without solvent or in a mixed solvent of dichloromethane and water. The reaction temperature can be set to any temperature from 0 ° C to the reflux temperature of the reaction mixture, but is preferably 0 ° C to room temperature.

[0096]

Embedded image

The starting material (X) in which Z is a sulfur atom comprises compound (IV) and hydrogen sulfide in the presence or absence of a base,
Obtained by reacting in an inert solvent. The base used is preferably an organic base such as triethylamine or pyridine. The solvent used is benzene,
Aromatic hydrocarbons such as toluene, diethyl ether, ethers such as tetrahydrofuran, dichloromethane,
Examples thereof include halogenated hydrocarbons such as 1,2-dichloroethane and water. The reaction temperature can be set to any temperature from 0 ° C to the reflux temperature of the reaction mixture. Generally, an organic base such as triethylamine is used as a base, and it is preferable to react with hydrogen sulfide at around room temperature in toluene.

In each method, the molar ratio of each reactant is not particularly limited, but it is advantageous to carry out the reaction in an equimolar ratio or a ratio close thereto.

When the compound of the present invention needs to be purified, it can be separated and purified by any purification method such as recrystallization, column chromatography, thin layer chromatography and the like.

When the compound of the present invention is applied as a pest control agent, it is generally a suitable carrier, for example, solid carrier such as clay, talc, bentonite, diatomaceous earth, white carbon or water, alcohols (isopropanol, butanol, benzyl alcohol). , Furfuryl alcohol etc.), aromatic hydrocarbons (toluene, xylene etc.), ethers (anisole etc.), ketones (cyclohexanone, isophorone etc.), esters (butyl acetate etc.), acid amides (N-methyl) (Pyrrolidone etc.) or halogenated hydrocarbons (chlorobenzene etc.) and the like can be mixed and applied, and if desired, a surfactant, an emulsifier, a dispersant, a penetrant, a spreading agent, a thickener, Antifreeze agents, anti-caking agents, stabilizers, etc. are added, and liquid agents, emulsions,
It can be put into practical use in any dosage form such as a wettable powder, a dry flowable agent, a flowable agent, a powder agent, and a granule.

In addition, the compound of the present invention may be used as a herbicide of other species, various insecticides, acaricides, nematicides, fungicides, plant growth regulators, synergists, fertilizers during formulation or spraying, if necessary. Alternatively, it may be mixed with a soil conditioner and applied.

Particularly, when mixed with other pesticides or plant hormones, it can be expected to reduce the cost by reducing the amount of the applied drug, to broaden the insecticidal spectrum due to the synergistic action of the mixed drugs, and to have a higher pest control effect. On this occasion,
It is also possible to combine a plurality of known pesticides at the same time. Examples of types of pesticides used in combination with the compound of the present invention include, for example, Farm Chemicals Handbook (Farm Chem
icals Handbook) Compounds described in the 1994 edition.

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

Next, formulation examples of preparations using the compound of the present invention will be shown concretely. However, the compounding examples of the present invention are not limited to these. In the following formulation examples, "part" means part by weight.

[Wettable powder] Compound of the present invention: 5 to 80 parts Solid carrier: 10 to 85 parts Surfactant: 1 to 10 parts ........ 1 to 5 parts Other examples include anti-caking agents.

[Emulsion] Compound of the present invention: 1 to 30 parts Liquid carrier: 30 to 95 parts Surfactant: 5 to 15 parts

[Flowable agent] Compound of the present invention: 5 to 70 parts Liquid carrier: 15 to 65 parts Surfactant: 5 to 12 parts Others: ..... 5 to 30 parts Other examples include antifreezing agents and thickeners.

[Granular wettable powder (dry flowable agent)] Compound of the present invention: 20 to 90 parts Solid carrier: 10 to 60 parts Surfactant:・ 1 to 20 copies

[Granule] Compound of the present invention: 0.1 to 10 parts Solid carrier: 90 to 99.9 parts Others: 1 to 5 parts

[Powder] Compound of the present invention: 0.01 to 30 parts Solid carrier: 67 to 99.5 parts Other :: 0 to 3 parts

[0111]

EXAMPLES Examples (Synthesis Examples, Formulation Examples, Test Examples) Hereinafter, the present invention will be specifically described with reference to Examples (Synthesis Examples, Formulation Examples, Test Examples).

[Synthesis Example] The compounds included in the present invention are
Although it can be produced or can be produced based on the synthetic examples shown below, the present invention is not limited to these compounds.

Synthesis Example 1 2- (2-chloro-6-fluorophenyl) -5- (4
-Chlorophenyl) -5-methyl-4 (5H) -imidazolinone (Compound No. 29 of the present invention) 2.76 g of phosphorus pentachloride is added to 23 ml of toluene, and the mixture is vigorously stirred. To this suspension solution, a solution prepared by dissolving 1.83 g of 2- (2-chloro-6-fluorobenzoylamino) -2- (4-chlorophenyl) propionamide in 21 ml of toluene was added dropwise, and after completion of the addition, the mixture was stirred overnight at room temperature. To continue. Subsequently, the reaction was completed by further stirring at 80 ° C. for 2 hours, after the reaction was completed, the mixture was allowed to cool to room temperature, then poured into 100 ml of ice water, and the mixture was continuously stirred until all the ice was dissolved. Next, a 50% aqueous sodium hydroxide solution was added under ice cooling to adjust the pH to 9 to 10, and then the mixture was extracted with 200 ml of ethyl acetate. The ethyl acetate layer is 100 water
After washing with ml, dehydration with saturated brine, drying over anhydrous sodium sulfate, and evaporation of the solvent under reduced pressure give a yellow oil. The yellow oil solidifies upon standing and is washed with a hexane-diisopropyl ether (1: 1) mixed solvent to give white crystals of the target compound 1.4.
2 g was obtained. (Yield 81.8%) Melting point: 182.5-184.0 ° C

Synthesis Example 2 2- (2-chlorophenyl) -5- (4-methoxyphenyl) -5-methyl-4 (5H) -imidazolinone (Compound No. 21 of the invention) 60% 150 mg of oily sodium hydride Toluene 15
Add to ml and heat to reflux. 2- (2-chlorobenzoylamino) -2- (4-methoxyphenyl)
900 mg of propionamide was carefully added and stirring was continued under reflux for 90 minutes. After continuing stirring at room temperature overnight, 50 ml of ice water was added and the mixture was extracted with 100 ml of ethyl acetate. The ethyl acetate layer was dehydrated with saturated brine, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain a pale yellow oil. The pale yellow oil solidifies upon standing and is washed with a mixed solvent of diisopropyl ether-hexane (8: 1) to give white crystals of the target compound.
0 mg was obtained. (Yield 87.1%) Melting point: 153.5-154.5 ° C

Synthesis Example 3 2- (2-Fluorophenyl) -5- (4-methoxyphenyl) -5-methyl-4 (5H) -imidazolinone (Compound No. 22 of the invention) 2- (2-Fluorobenzoyl) Amino) -2- (4-methoxyphenyl) propionamide (800 mg) was dissolved in phosphorus oxychloride (6 ml), and phosphorus pentachloride (1.05 g) was added to the mixture, and stirring was continued overnight at room temperature. After phosphorus oxychloride is distilled off under reduced pressure, 30 ml of toluene is added and toluene is distilled off under reduced pressure. This operation was repeated 3 times to completely remove phosphorus oxychloride in the system, and then water 50m
1 was added and the mixture was heated under reflux for 1 hour. After allowing to cool to room temperature, add 50% aqueous sodium hydroxide solution under ice cooling and add p.
After setting H to 10 to 11, extraction was performed with 100 ml of ethyl acetate. The ethyl acetate layer was dehydrated with saturated brine, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain a yellow oil. This yellow oil solidifies upon standing and is washed with a diisopropyl ether-hexane (6: 1) mixed solvent to give 630 m of white crystals of the target compound.
g was obtained. (Yield 83.5%) Melting point: 121.5-122.5 ° C

Synthesis Example 4 2- (2-Fluorophenyl) -5- (4-trifluoromethylphenyl) -5-methyl-4 (5H) -imidazolinone (Invention Compound No. 13) 2- (2- Fluorobenzoylamino) -2- (4-trifluoromethylphenyl) propionamide 900 m
g was dissolved in 5 ml of 1,4-dioxane, 6.7 ml of a 2N sodium hydroxide aqueous solution was added, and the mixture was added at 100 ° C. to 3.
Stir for 5 hours. After the reaction was completed, the mixture was allowed to cool to room temperature and water 100
It was poured into 100 ml and extracted with 100 ml of ethyl acetate. The aqueous layer was further extracted with 50 ml of ethyl acetate, the ethyl acetate layers were combined, dehydrated with saturated brine, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain a yellow oil. The yellow oil solidified upon standing and was washed with a mixed solvent of diisopropyl ether-hexane (1: 1) to obtain 770 mg of a white crystal of the target compound. (Yield 90.1%) Melting point: 139.0-140.0 ° C

Synthesis Example 5 2- (2-chlorophenyl) -5- (4-trifluoromethoxyphenyl) -5-methyl-4 (5H) -imidazolinone (invention compound No. 63) 2- (2-chloro) Benzoylamino) -2- (4-trifluoromethoxyphenyl) propionitrile 1.07
g was dissolved in 5 ml of ethyl alcohol, and 3 ml of water was added. 0.9 ml of 50% aqueous sodium hydroxide solution was added to the mixture under ice cooling, and 1.6 ml of 30% aqueous hydrogen peroxide solution was further added dropwise at 20-30 ° C. After stirring at 50-60 ° C. for 1.5 hours, stirring was continued for 1 hour under reflux to complete the reaction, and after the reaction was completed, the mixture was allowed to cool to room temperature, poured into 100 ml of water, and 200 ml of ethyl acetate. Extracted. After washing the ethyl acetate layer with 100 ml of water,
Dehydrated with saturated saline, dried over anhydrous sodium sulfate,
Evaporation of the solvent under reduced pressure gives a yellow oil. By subjecting this to trituration in a mixed solvent of diisopropyl ether-hexane (1: 3), milk-white crystals of the target compound 6
50 mg was obtained. (Yield 60.8%) Melting point: 152-153 ° C

Synthesis Example 6 2- (2-Fluorophenyl) -5- (4-chlorophenyl) -5-methyl- (5H) -imidazoline-4-thione (invention compound No. 55) 2- (2-fluoro) 2.78 g of benzoylamino) -2- (4-chlorophenyl) thiopropionamide
It was dissolved in 16 ml of 4-dioxane, 22 ml of 2N aqueous sodium hydroxide solution was added, and the mixture was stirred at 100 ° C. for 6 hours. After completion of the reaction, the mixture was allowed to cool to room temperature, poured into 200 ml of water, adjusted to pH 6 by adding concentrated hydrochloric acid, and then washed with ethyl acetate 2
It was extracted with 00 ml. The ethyl acetate layer was dehydrated with saturated saline and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain yellow crystals. This was washed with diisopropyl ether to obtain 1.96 g of lemon-colored crystals of the target compound. (Yield: 74.5%) The target compound was almost completely 2- (2-fluorophenyl) -4- (4-chlorophenyl) -under ¹ H NMR measurement conditions using a heavy chloroform-deuterium dimethyl sulfoxide solvent. 4-methyl-5-mercapto- (4H)
It was isomerized to imidazole. Melting point: 177.5-178.0 ° C

Reference Example 1 2- (2-Fluorobenzoylamino) -2- (4-bromophenyl) -propionamide 1.2 g of 2-amino-2- (4-bromophenyl) propionamide was dissolved in 10 ml of tetrahydrofuran. ,
550 mg of triethylamine was added. While stirring under ice-cooling, 2-fluorobenzoyl chloride 790 mg
Was added dropwise to 10 ml of tetrahydrofuran, and after completion of the dropwise addition, stirring was continued overnight at room temperature. After completion of the reaction, add to 200 ml of ethyl acetate, and add 3 m hydrochloric acid 100 m.
1, water 50 ml, sodium hydrogen carbonate aqueous solution 100 ml
Were washed in this order, dehydrated with saturated saline and dried over anhydrous sodium sulfate. When the solvent was distilled off under reduced pressure, a pale yellow oily substance remained, which solidified when left standing. The solid was triturated and washed with a diisopropyl ether-hexane mixed solvent to obtain 1.99 g of the title compound as white crystals. (Yield 99%) Melting point: 104.0-107.0 ° C (decomposition)

Reference Example 2 2- (2-chlorobenzoylamino) -2- (4-methoxyphenyl) pyropionamide 2- (2-chlorobenzoylamino) -2- (4-methoxyphenyl) propionitrile 2. 0 g is dissolved in 15 ml of dichloromethane, 0.6 ml of water is added, and the mixture is vigorously stirred under ice cooling. Concentrated sulfuric acid (2 ml) was carefully added dropwise at the same temperature, and after completion of the addition, stirring was continued for 2 hours under ice cooling. After completion of the reaction, 15 ml of dichloromethane was added, and then 50% aqueous sodium hydroxide solution was added while appropriately adding water so that the temperature did not rise excessively, and the pH was adjusted to 11 to 11.
It was extracted at 12 with 100 ml of ethyl acetate. The ethyl acetate layer was washed with 50 ml of water, dehydrated with saturated brine and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain a pale yellow oil. White crystals of the title compound were obtained by triturating this in diisopropyl ether.
09 g were obtained. (Yield 98.9%) Melting point: 144.5-145.5 ° C

Reference Example 3 2- (2-chlorobenzoylamino) -2- (4-chlorophenyl) thiopropionamide 2.93 g of 2- (2-chlorobenzoylamino) -2- (4-chlorophenyl) propionitrile Toluene 7
It was dissolved in 5 ml and 950 mg of triethylamine was added. The mixture was stirred at room temperature while slowly bubbling hydrogen sulfide for 2 hours, the container was further sealed, and stirring was continued overnight. Nitrogen gas is blown in to drive off excess hydrogen sulfide gas, and then the solvent is distilled off under reduced pressure to obtain a yellow solid. This solid was washed with a mixed solvent of diisopropyl ether-hexane (2: 1) to obtain 3.18 g of a pale yellow crystal of the title compound. (Yield 98.1%) Melting point: 188-192 ° C (decomposition)

The compounds shown in Table 2 were synthesized according to the above synthesis examples.

Table 2

[0124]

[Chemical 17]

[0125]

[Table 46] ────────────────────────────────── No. R ¹ R ² X _l Y _m Z Melting point ────────────────────────────────── 1 H CH ₃ 2-Cl 4-Cl O 199.0-200.0 2 H CH ₃ 2,6-F ₂ 4-Cl O 188.5-189.0 3 H CH ₃ 2-CH = CH-CH = CH-3 4-Cl O 196.0-197.0 4 H CH ₃ 2-Br 4-Cl O 199.5- 200.0 5 H CH ₃ 2-CF ₃ 4-Cl O 158.5-160.0 6 H CH ₃ 2-OCH ₃ 4-Cl O 137.5-138.5 7 H CH ₃ 2-CH ₃ 4-Cl O 187.5-189.0 8 H CH ₃ 2,6-Cl ₂ 4-Cl O 196.0-197.0 9 H CH ₃ 3-Cl 4-Cl O 185.5-187.5 10 H CH ₃ 4-Cl 4-Cl O 225.0-227.0 11 H CH ₃ 2-F 4- Cl O 152.5-154.0 12 H CH ₃ 2-Cl 4-CF ₃ O 159.5-161.0 13 H CH ₃ 2-F 4-CF ₃ O 139.0-140.0 14 H CH ₃ 2,6-F ₂ 4-CF ₃ O 174.0-175.5 15 H CH ₃ 2-Cl 4-Br O 199.5-200.0 16 H CH ₃ 2-F 4-Br O 160.0-161.0 17 H CH ₃ 2,6-F ₂ 4-Br O 185.5-187.0 18 H CH ₃ 2-Cl 3,4-Cl ₂ O 168.0-169.0 19 H CH ₃ 2-F 3,4-Cl ₂ O 185.0-186.0 20 H CH ₃ 2,6-F ₂ 3,4-Cl ₂ O 208.0 -209.0 21 H CH ₃ 2-Cl 4-OCH ₃ O 153.5 -154.5 22 H CH ₃ 2-F 4-OCH ₃ O 121.5-122.5 23 H CH ₃ 2,6-F ₂ 4-OCH ₃ O 174.0-175.0 ─────────────── ────────────────────

[0126]

[Table 47] ────────────────────────────────── No. R ¹ R ² X _l Y _m Z Melting point ────────────────────────────────── 24 H CH ₃ 2-F 3-Cl O 144.0-144.5 25 H CH ₃ 2-Cl 3-Cl O 132.0-133.0 26 H CH ₃ 3-Cl 3-Cl O 158.0-160.0 27 H CH ₃ 4-Cl 3-Cl O 212.0-215.0 28 H CH ₃ 2,6-F ₂ 3-Cl O 172.0-173.0 29 H CH ₃ 2-Cl-6-F 4-Cl O 182.5-184.0 30 H CH ₃ 2-Cl-6-F 4-Br O 188.5-189.0 31 H CH ₃ 2-Cl -6-F 3,4-Cl ₂ O 164.0-166.0 32 H CH ₃ 2-Cl-6-F 4-OCH ₃ O 177.0-177.5 33 H CH ₃ 2-F 4-CH ₃ O 138.0-139.0 34 H CH ₃ 2-Cl 4-CH ₃ O 199.0-201.0 35 H CH ₃ 2,6-F ₂ 4-CH ₃ O 174.0-176.0 36 H CH ₃ 2,5-F ₂ 4-CH ₃ O 130.0-131.0 37 H CH ₃ 2-F 4-FO 131.0-132.0 38 H CH ₃ 2-Cl 4-FO 157.0-158.0 39 H CH ₃ 2,6-F ₂ 4-FO 178.0-180.0 40 H CH ₃ 2,5-F ₂ 4-FO 134.0-135.0 41 H CH ₃ 2-F 2-Cl O 194.0-195.0 42 H CH ₃ 2-Cl 2-Cl O 214.0-214.5 43 H CH ₃ 2,6-F ₂ 2-Cl O 233.0 -234.0 44 H CH ₃ 4-Cl 2-Cl O 209.0-210. 0 45 H CH ₃ 3-Cl 2-Cl O 159.0-162.0 46 H CH ₂ CH ₃ 2-F 4-Cl O 131.0-133.0 ──────────────────── ───────────────

[0127]

[Table 48] ────────────────────────────────── No. R ¹ R ² X _l Y _m Z Melting point ────────────────────────────────── 47 H CH ₂ CH ₃ 2-Cl 4-Cl O 152.0-154.0 48 H CH ₂ CH ₃ 2,6-F ₂ 4-Cl O 157.0-159.0 49 H CH ₂ CH ₃ 2,6-Cl ₂ 4-Cl O 165.0-166.0 50 H CH ₃ 2,6-Cl ₂ 2- Cl O 225.0-227.0 51 H CH ₃ 2-F 4-OH O 268.0-271.0 52 H CH ₃ 2-Cl 4-OH O 228.0-230.0 53 H CH ₃ 2-F 4-O (Q38-3-Cl- 5-CF ₃ ) O oil 54 H CH ₃ 2-Cl 4-O (Q38-3-Cl-5-CF ₃ ) O oil 55 H CH ₃ 2-F 4-Cl S 177.5-178.0 56 H CH ₃ 2-Cl 4-Cl S 192.0-193.0 57 H CH ₃ 2-F 3,4-F ₂ O 128.0-131.0 58 H CH ₃ 2-Cl 3,4-F ₂ O 121.0-124.0 59 H CH ₃ 2 , 5-F ₂ 4-Cl O 147.0-148.0 60 H CH ₃ 2,6-F ₂ 3,4-F ₂ O 172.0-174.0 61 H CH ₃ 2,6-Cl ₂ 3,4-F ₂ O 203.0 -204.0 62 H CH ₃ 2-F 4-OCF ₃ O 110.5-112.5 63 H CH ₃ 2-Cl 4-OCF ₃ O 152.0-153.0 64 H CH ₃ 2,3-F ₂ 4-Cl O 127.0-129.0 65 H CH ₃ 2,4-F ₂ 4-Cl O 119.0-121.0 66 H CH ₃ 2-F 4-C ( CH ₃ ) ₃ O 151.0-152.0 67 H CH ₃ 2-Cl 4-C (CH ₃ ) ₃ O 186.0-189.0 68 H CH ₃ 2-F 3-F-4-Br O 182.0-184.0 69 H CH ₃ 2 -F 4-NO ₂ O 168.0-170.0 ──────────────────────────────────

[0128]

[Table 49] ────────────────────────────────── No. R ¹ R ² X _l Y _m Z Melting point ────────────────────────────────── 70 H CH ₂ CH ₂ CH ₃ 2-F 4-Cl O 120.0 -121.0 ──────────────────────────────────

Formulation Examples Next, formulation examples of pest control agents containing the compound of the present invention as an active ingredient are shown, but the present invention is not limited thereto. In the following formulation examples, "part" means part by weight.

[Formulation Example 1] Wettable powder Compound of the present invention: 50 parts Diklite PFP: 43 parts (Kaolin clay: Sikhlite Industry Co., Ltd.) Product name: Solpol 5050 ・ ・ ・ ・ ・ ・ ・ ・ 2 parts (Anionic surfactant: Toho Chemical Industry Co., Ltd. product name) Lunox 1000 C ・ ・ ・ ・ ・ ・ 3 parts (Anionic interface Activator: Toho Chemical Industry Co., Ltd. product name) Carplex # 80 (anti-caking agent) ... 2 parts (white carbon: Shionogi Pharmaceutical Co., Ltd. product name) Use as an agent.

Formulation Example 2 Emulsion Compound of the present invention: 3 parts xylene: 76 parts Isophorone: 15 parts Solpol 3005X ..... 6 parts (mixture of nonionic surfactant and anionic surfactant: trade name of Toho Chemical Industry Co., Ltd.) The above components are uniformly mixed to form an emulsion.

Formulation Example 3 Flowable Agent Compound of the present invention: 35 parts Agrisol S-711: 8 parts (Nonionic surfactant: Kao (stock) ) Brand name) Lunox 1000 C ・ ・ ・ ・ ・ ・ 0.5 parts (Anionic surfactant: Toho Chemical Industry Co., Ltd. product name) 1% Rhodopol water ・ ・ ・ ・ ・ ・ 20 parts ( Thickener: Trade name of Lorne Poulin Co., Ltd. Ethylene glycol (antifreeze) ... 8 parts Water ... 28.5 parts Mix the above uniformly to make a flowable agent.

[Formulation Example 4] Granular wettable powder (dry flowable agent) Compound of the present invention: 75 parts Isoban No. 1: 10 parts (anionic interface Activator: Kuraray Isoprene Chemical Co., Ltd. product name) Vanillex N ........ 5 parts (Anionic surfactant: Sanyo Kokusaku Pulp Co., Ltd. product name) Carplex # 80 ... 10 parts (white carbon: trade name of Shionogi Seiyaku Co., Ltd.) The above components are uniformly mixed and pulverized to obtain a dry flowable agent.

[Formulation Example 5] Granules Compound of the present invention: 0.1 part Bentonite: 55.0 parts Talc :: 44.9 parts After being uniformly mixed and pulverized, a small amount of water is added, and the mixture is kneaded with stirring, granulated by an extrusion granulator, and dried to give granules.

[Formulation Example 6] Powder Compound of the present invention: 3.0 parts Carplex # 80: 0.5 part (White carbon: Shionogi Pharmaceutical Co., Ltd. ) Product name) Clay ・ ・ ・ ・ ・ ・ 95 parts Diisopropyl phosphate ・ ・ ・ ・ ・ ・ ・ ・ 1.5 parts The above is uniformly mixed and pulverized to give a powder.

In use, the wettable powder, emulsion, flowable powder and granular wettable powder are diluted 50 to 20000 times with water to prepare an active ingredient in an amount of 0.005 to 5 per hectare (ha).
Sprinkle so that it weighs 0 kg.

[Test Example] Next, the usefulness of the compound of the present invention as a pest control agent will be specifically described in the following test examples.

Test Example 1 Insecticidal test against brown planthopper 5% emulsion of the compound of the present invention described in the specification (25% wettable powder depending on the compound was tested) was diluted with water containing a spreader, and 1000 The drug solution was prepared to have a ppm concentration. 1/2 this chemical
A sufficient amount was applied to the foliage of rice planted in a pot of 0,000 are. After air-drying, a cylinder was set up, 10 second-instar larvae of the brown planthopper were released per pot, capped, and stored in a temperature-controlled room. The survey was conducted after 6 days, and the mortality rate was calculated from the following formula. The test was conducted in a two-division system.

Mortality of mortality (%) = (number of mortality / number of larvae) × 100 As a result, the following compounds showed a mortality of 100%.

Compound of the present invention: No. 11, 13, 19,
22, 33, 35, 37, 57, 62, 64, 65.

Test Example 2 Insecticidal test against pearl oyster ladybird 5% emulsion of the compound of the present invention described in the specification (25% wettable powder depending on the compound was used) was diluted with water containing a spreading agent. Then, adjust to a chemical solution of 1000ppm concentration, soak the tomato leaves in this solution for about 10 seconds, air-dry and place in a petri dish.
The head was released and the lid was put on it and stored in a thermostatic chamber at 25 ° C, and the mortality rate after 6 days was calculated from the following formula. The test was conducted in a two-division system.

Mortality of mortality (%) = (number of mortality / number of mortality) × 100 As a result, the following compounds showed a mortality of 100%.

Compounds of the Invention: No. 1, 2, 4, 5,
8, 11, 12, 13, 15, 16, 17, 18, 1
9, 24, 29, 31, 32, 33, 37, 38, 4
0, 42, 46, 47, 50, 54, 55, 56, 5
7,58,59,62,63,64,65,68,6
9.

[0144]

INDUSTRIAL APPLICABILITY The compound of the present invention has excellent insecticidal and acaricidal activity against many agricultural pests and spider mites, and has almost no adverse effect on mammals, fish and beneficial insects. Therefore, the compound of the present invention can provide a useful pest control agent.

 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Masaki Kudo 3-7-1 Kanda Nishikicho, Chiyoda-ku, Tokyo Nissan Chemical Industry Co., Ltd. Institute of Biological Sciences, Inc. (72) Inventor Toshiro Miyake 1470 Shiraoka, Shiraoka-cho, Minamisaitama-gun, Saitama Nissan Chemical Industry Co., Ltd., Institute of Biological Sciences

Claims (4)

[Claims] 1. A compound of the general formula (I) [In the formula, R ¹ is a hydrogen atom, a C _{1 to} C ₆ alkyl group, a C _{3 to} C ₆ cycloalkyl group, a C _{2 to} C ₆ alkenyl group, a C _{2 to} C ₆ alkynyl group, and a C _{1 to} C ₆ haloalkyl group. , C _{2 to} C ₆ alkoxyalkyl group, formyl group, C _{2 to} C ₆ alkylcarbonyl group, C _{2 to} C ₆
Alkoxycarbonyl group, C ₃ -C ₆ alkoxycarbonylalkyl group, C ₂ -C ₆ cyanoalkyl group, a benzyl group, a phenyl group, a cyano group, an amino group, C ₃ -C ₆ alkoxycarbonyl group, -SR ¹⁰ group { However, R ¹⁰ is a C _{2 to} C ₆ alkoxycarbonyl group, a C _{1 to} C ₆ alkylsulfonyl group,
-NR ¹¹ R ¹² group (provided that R ¹¹ represents a C ₁ -C ₆ alkyl group, R
¹² C ₁ -C ₆ alkyl group, C ₂ -C ₆ alkoxycarbonyl group, C ₃ -C ₉ alkoxycarbonylalkyl group, C ₁ -C ₆ alkylsulfonyl group, C ₂ -C ₆ alkylcarbonyl group, C ₃
~ C ₉ dialkylaminocarbonyl group, C ₂ ~ C ₆ dialkylaminosulfonyl group or an unsubstituted or optionally substituted phenyl group), or an unsubstituted or optionally substituted phenyl group (provided that it is substituted) Examples of the substituent group optionally halogen atom, a cyano group, a nitro group, C ₁ -C ₄ alkyl group, C ₁ -C ₄ haloalkyl groups, C ₁ -C ₄
Alkoxy groups, C ₁ -C ₄ haloalkoxy groups, C ₁ -C ₄ alkylthio group, C ₁ -C ₄ haloalkylthio group, C ₂ -C ₆ alkoxycarbonyl group, C ₂ -C ₆ haloalkoxycarbonyl groups,
C _{2 to} C ₆ alkylcarbonyl group, C _{2 to} C ₆ haloalkylcarbonyl group, C _{1 to} C ₄ alkylsulfonyl group or C _{1 to} C ₄ haloalkylsulfonyl group is shown, and when there are two or more substituents, the substituent is May be the same or different). }, An alkali metal or an alkaline earth metal, and R ² is a hydrogen atom, a C _{1 to} C ₆ alkyl group, a C _{3 to} C ₆ cycloalkyl group, a C _{2 to} C ₆ alkenyl group, or a C _{2 to} C ₆ alkynyl group. , C ₅ ~
C ₆ cycloalkenyl group, C ₁ -C ₆ haloalkyl group, C ₂ -C ₆
Alkoxyalkyl group, C ₃ -C ₆ halocycloalkyl group,
C ₂ -C ₆ haloalkenyl group, C ₂ -C ₆ haloalkynyl group, or an unsubstituted or optionally substituted phenyl group (wherein the substituent is as the substituent also be a halogen atom,, C ₁ -C ₄ alkyl groups, C _{1 to} C ₄ haloalkyl groups, C ₁
~ C ₄ alkoxy group, C ₁ ~ C ₄ haloalkoxy group, C ₁ ~ C ₄ alkylthio group or C ₁ ~ C ₄ haloalkylthio group,
When the number of the substituents is two or more, the substituents may be the same or different, and X is a halogen atom, a C _{1 to} C ₄ alkyl group, a C _{1 to} C ₄ alkoxy group, a C ₁ to C ₄ alkylthio groups, C ₁ -C ₄ haloalkyl group,
C ₁ -C ₄ haloalkoxy groups, C ₁ -C ₄ haloalkylthio group,
Represents an amino group, a cyano group, or a nitro group, and l is 1 to
5 is an integer (provided that in the case of 2 to 5, X may be the same or different), Y is a halogen atom, a C _{1 to} C ₆ alkyl group, a C _{2 to} C ₆ alkenyl group, C ₂ -C ₆ alkynyl group, C ₃ -C ₆ cycloalkyl group,
C ₁ -C ₆ haloalkyl group, C ₂ -C ₆ haloalkenyl group, C ₂ ~
C ₆ haloalkynyl group, C _{3 to} C ₆ halocycloalkyl group, C ₂
~ C ₆ cyanoalkyl group, C ₁ ~ C ₆ hydroxyalkyl group,
C ₂ -C ₆ carboxyalkyl group, C ₁ -C ₆ alkoxy group, C ₂
To C ₆ alkenyloxy group, C _{2 to} C ₆ alkynyloxy group,
C ₃ -C ₆ cycloalkyloxy groups, C ₁ -C ₆ haloalkoxy groups, C ₂ -C ₆ haloalkenyloxy groups, C ₂ -C ₆ haloalkynyloxy groups, C ₃ -C ₆ halocycloalkyl alkoxy groups, C _4- C ₇
Halocycloalkyl alkoxy group, C ₁ -C ₆ alkylthio group, C ₂ -C ₆ alkenylthio group, C ₂ -C ₆ alkynylthio, C ₃ -C ₆ cycloalkylthio group, C ₁ -C ₆ haloalkylthio group, C ₁ -C ₆ alkylsulfinyl group, C ₂ -C ₆ alkenylsulfinyl group, C ₂ -C ₆ alkynylsulfinyl group, C ₃ -C ₆ cycloalkyl alkylsulfinyl group, C ₁ -C ₆ haloalkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, C ₂ -C ₆ alkenylsulfonyl group, C ₂ -C ₆ alkynylsulfonyl group, C ₃ -C ₆ cycloalkylsulfonyl group, C ₁
-C ₆ haloalkylsulfonyl group, C ₂ -C ₆ alkoxyalkyl group, C ₂ -C ₆ alkoxyalkoxy, C ₂ -C ₆ haloalkoxyalkyl group, C ₂ -C ₆ haloalkoxy alkoxy group, C ₂ -C ₆ alkylthioalkyl group, C ₂ -C ₆ alkylthioalkoxy group, C ₃ -C ₆ alkoxycarbonylalkyl group, C ₃ -C ₆ alkylcarbonyl group, C ₂ -C ₆ alkoxycarbonyloxy group, C ₂ -C ₆ alkylcarbonyl oxy group, C ₂ -C ₆ alkylcarbonyl group, C ₃ -C ₆ alkenylcarbonyl group, C ₃ -C ₆ alkynyl group, C ₄
To C ₇ cycloalkylcarbonyl group, C _{2 to} C ₆ haloalkylcarbonyl group, C _{2 to} C ₆ alkoxycarbonyl group, C _{2 to} C ₆
Haloalkoxycarbonyl groups, C ₃ -C ₆ alkoxycarbonylalkoxy group, nitro group, cyano group, hydroxy group, carboxyl group, thiocyanate group, isothiocyanate group, C ₂ -C ₆ thiocyanate alkyl group, C ₁ -C ₆ alkylsulfonyl oxy group, C ₂ -C ₆ alkylthiocarbonyl group, an amino group (-NR ³ R ^4), aminocarbonyl group (-CONR
³ R ⁴ ), aminocarbonyloxy group (-OCONR ³ R ⁴ ), amido group (-NR ³ COR ⁴ ), alkoxycarbonylamino group (-NR ³ CO ₂
R ⁴ ), aminosulfonyl group (-SO ₂ NR ³ R ⁴ ), thioamide group
(-NR ³ CSR ⁴ ), methylenedioxy group, halomethylenedioxy group, ethylenedioxy group, haloethylenedioxy group,
Trimethylsilyl group or {However, W is (However, R ³ and R ⁴ are each independently a hydrogen atom, C _{1 to} C ₆
Alkyl group, C ₂ -C ₆ alkenyl group, C ₂ -C ₆ alkynyl group, C ₁ -C ₆ haloalkyl group, C ₂ -C ₆ haloalkenyl group,
C ₂ -C ₆ haloalkynyl group, C ₂ -C ₆ alkylcarbonyl group, C ₂ -C ₆ alkoxycarbonyl group, a phenyl group or a benzyl group, R ⁵ and R ⁶ are each independently hydrogen atom, a halogen atom , A C ₁ -C ₆ alkyl group, a C ₃ -C ₆ cycloalkyl group, a cyano group or a phenyl group, and q represents an integer of 0-2. ), N is an integer of 0 or 1, Ar is an unsubstituted or optionally substituted phenyl group, naphthyl group, furyl group, thienyl group, pyrrolyl group, pyrazolyl group, imidazolyl group, thiazolyl group, isothiazolyl group. Group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, triazolyl group, pyridyl group, pyridazyl group, pyrimidyl group, pyrazyl group, quinolyl group or quinoxalyl group (however, a substituent which may be substituted is a halogen atom, cyano group, nitro group, C ₁ -C ₄ alkyl group, C ₁ -C ₄ haloalkyl groups, C ₁ ~
C ₄ alkoxy, C ₁ -C ₄ Haroarukikoshi group, C ₁ -C ₄ alkylthio group, C ₁ -C ₄ haloalkylthio group, C ₁ -C ₄ alkylsulfonyl group, C ₁ -C ₄ haloalkylsulfonyl groups, C ₂
~ C ₄ alkoxycarbonyl group, carboxyl group, amino group, mono C ₁ -C ₄ alkylamino group, di C ₁ -C ₄ alkylamino group, phenyl group, benzyl group, methylenedioxy group or halomethylenedioxy group In the case where there are two or more substituents, the substituents may be the same or different. }, M represents an integer of 1 to 5 (provided that in the case of 2 to 5, Y may be the same or different), and Z represents an oxygen atom, a sulfur atom or an imino group. ] The imidazolinone derivative represented by 2. R ¹ and R ² are each independently a hydrogen atom or C _1.
To C ₆ alkyl group, X is a halogen atom, C _{1 to} C ₆ haloalkyl group or C _{1 to} C ₆
An alkoxy group, wherein Y is a halogen atom, a C _{1 to} C ₆ alkyl group, a C _{1 to} C ₆ alkoxy group, a C _{1 to} C ₆ haloalkyl group, a C _{1 to} C ₆ haloalkoxy group, a nitro group or a substituted May be a pyridyloxy group (provided that the optionally substituted substituent is a halogen atom, a cyano group, a nitro group, a C _{1 to} C ₆ haloalkyl group or a C _{1 to} C ₆ haloalkoxy group, and Z is an oxygen atom). The imidazolinone derivative according to claim 1, wherein l represents an integer of 1 or 2, and m represents an integer of 1 to 3. 3. A pest control agent comprising one or more of the imidazolinone derivative according to claim 1 as an active ingredient. 4. A pest control agent comprising one or more of the imidazolinone derivatives according to claim 2 as an active ingredient.