JPH07165697A - Semiconductor compound and pest-controlling agent - Google Patents

Abstract

PURPOSE:To obtain a new compound capable of effectively controlling insect pests of Orthoptera, Hemiptera, Lepidoptera, Coleoptera, Hymenoptera, Diptera, Isoptera, and Acarina and Anoplura and hardly having undesirable influence on mammal, fishes and beneficial insects. CONSTITUTION:A compound of formula I [W is 0 or S; X, Y and Z are Cl, Br, OH, cyano, etc.; R<1> to R<4> each is H, a 1-6C alkyl; (1) and (m) are each an integer of 0-5; (n) is an integer of 1-5], e.g. N(4-chlorophenyl)-4- chlorobenzamide-4trifluoromethoxysemicarbazone. For example, this compound is obtained by reacting a compound of formula II with phosphorus pentachloride without using a solvent to afford a compound of formula III, reacting the compound of formula III with a compound of formula IV in an inert solvent to give a compound of formula V and further reacting the compound of formula V with a compound of the formula R<2>L<1> (L<1> is a halogen or an alkylsulfonate) in the presence of a base in an inert solvent.

Description

Detailed Description of the Invention

[0001]

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

[0002]

2. Description of the Related Art Conventionally, regarding the semicarbazone compounds of benzamide, European Journal of Medicinal Chemistry [Eur. J. Med. Che
m. , 26 , 273 (1991)] 4-RC ₆ H ₄ C =
(NHC ₆ H ₄ R'-4) NNHCWNHR "(where R
= H, MeO, Me, Cl , NO 2; R '= H, Me
O, Me, Cl; R ″ = Ph; W = O, S) are known, but R ″ is only unsubstituted phenyl,
Substituted phenyl is new. Further, although this document shows activity as a medicine, it does not disclose any activity against pests.

[0003]

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.

As a result of intensive studies on the semicarbazone compound, the present inventors have found that the novel benzanid semicarbazone compound exhibits excellent insecticidal activity at a low dose and has almost no adverse effect on mammals, fish and beneficial insects. The present invention has been completed by discovering that the compound is a very useful compound having no

[0005]

The present invention has the general formula [I]

[0006]

[Chemical 2]

[In the formula, W represents an oxygen atom or a sulfur atom, and X, Y, and Z are each independently a halogen atom, a hydroxyl group, a cyano group, a nitro group, an SCN group, a trimethylsilyl group, R ⁹ , OR ⁹ , S (O) _p R ⁹ group, OS (O) ₂ R
⁹ groups, OC (O) R ⁹ groups, C (O) R ⁹ groups, CO ₂ R ⁹ groups,
C (O) N (R ⁹ ) R ¹⁰ group, SO ₂ N (R ⁹ ) R ¹⁰ group, N
HC (O) R ⁹ group, N (R ⁹ ) R ¹⁰ group, -CH = CH-CH = CH- group formed between adjacent carbon atoms, -OCH
₂ O- group, -OCH ₂ CH ₂ O- group, -OCF ₂ O- group,-
OCF ₂ CF ₂ O- group or -OCF ₂ CF ₂ - represents a group,
R ¹ represents a hydrogen atom, a C ₁ -C ₆ alkyl group optionally substituted by R ⁵ , R ⁵ or a phenyl group optionally substituted by (R ⁵ ) _q , and R ² , R ³ , 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, a C _{1 to} C ₆ haloalkyl group, a C _{2 to} C ₆ alkoxyalkyl group, C ₂ -C ₆ alkylcarbonyl groups, C ₂ -C ₆ alkoxycarbonyl groups, C
₂ -C ₆ haloalkylcarbonyl group, C ₁ -C ₆ alkylthio group, C ₁ -C ₆ haloalkylthio group, R ⁶ OC (O) N
(R ⁷ ) S-group, R ⁷ (R ⁸ ) NS-group or a benzyl group which may be substituted by (R ⁵ ) _q , wherein R ⁵ is a halogen atom, a hydroxyl group, a cyano group, a nitro group or C ₁ ~ C ₆
Alkyl group, C ₁ -C ₆ haloalkyl group, C ₁ -C ₆ alkoxy group, C ₁ -C ₆ haloalkoxy group, C ₁ -C ₆ alkylthio group, C ₁ -C ₆ haloalkylthio group, C ₁ -C ₆ An alkylsulfonyl group, a C ₁ -C ₆ haloalkylsulfonyl group,
C ₂ -C ₆ alkoxycarbonyl group, an amino group or a di C
_{1 to} C ₆ alkylamino group is shown, and R ⁶ , R ⁷ and R ⁸ are each independently a C _{1 to} C ₆ alkyl group, a phenyl group optionally substituted by (R ⁵ ) _q or (R ⁵ ) represents a benzyl group optionally substituted by _q , R ⁹ is a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ haloalkyl group, a C ₂ -C ₆ alkenyl group, a C ₂ -C ₆ haloalkenyl group, C ₂ -C ₆ alkynyl group, C ₂ -C ₆ haloalkynyl group, C ₃ -C ₆ cycloalkyl group, C ₃ -C ₆ halocycloalkyl group, C ₄ -C ₇ cycloalkylalkyl, C ₂ -C ₆ An alkoxyalkyl group,
C ₂ -C ₆ alkylthioalkyl group, C ₂ -C ₆ alkoxycarbonyl group, C ₂ -C ₆ cyanoalkyl radical,
(R ⁵ ) a phenyl group _optionally substituted by _q ,
(R ⁵ ) represents a benzyl group optionally substituted by _q or a pyridyl group optionally substituted by (R ⁵ ) _r , R ¹⁰ represents a hydrogen atom or a C ₁ -C ₆ alkyl group, and k represents Represents an integer of 0 to 2, l represents an integer of 0 to 5 (provided that when 1 is 2 to 5, X may be the same or different), and m represents an integer of 0 to 5 (however. , M is 2
In the case of 5, Y may be the same or different, and n is an integer of 1 to 5 (provided that when n is 2 to 5, Z may be the same or different). , P is 0
2 indicates an integer of 2 and q is an integer of 0 to 5 (however, q is 2 to
In the case of 5, R ⁵ may be the same or different, and r is an integer of 0 to 4 (provided that r is 2 to 4 R
⁵ may be the same or different). ] It is related with the semicarbazone compound represented by these, and the pest control agent which contains 1 type (s) or 2 or more types of this compound 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- means iso, sec- means secondary, t- means tertiary, and c- means cyclo.

As the C ₁ -C ₆ alkyl group, 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.

As the C ₂ -C ₆ alkoxyalkyl group,
Examples thereof include a methoxymethyl group, an ethoxymethyl group and a 1-methoxyethyl group.

As the C ₂ -C ₆ alkylcarbonyl group,
Methylcarbonyl group, ethylcarbonyl group, n-propylcarbonyl group, i-propylcarbonyl group, c-propylcarbonyl group, n-butylcarbonyl group, i-butylcarbonyl group, sec-butylcarbonyl group, t-butylcarbonyl group, Examples thereof include c-butylcarbonyl group.

The C ₂ -C ₆ alkoxycarbonyl group includes methoxycarbonyl group, ethoxycarbonyl group, n
-Propoxycarbonyl group, i-propoxycarbonyl group, c-propoxycarbonyl group, n-butoxycarbonyl group, i-butoxycarbonyl group, sec-butoxycarbonyl group, t-butoxycarbonyl group, c-butoxycarbonyl group and the like. .

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

Examples of W include an oxygen atom and a sulfur atom, preferably an oxygen atom.

X, Y and Z are each independently halogen.
Atom, hydroxyl group, cyano group, nitro group, SCN group, trime
Cylsilyl group, C₁~ C₆Alkyl group, C₁~ C₆Halo al
Kill group, C₂~ C₆Alkenyl group, C₂~ C₆Halo archeni
Lu group, C₂~ C₆Alkynyl group, C₂~ C₆Haloalkynyl
Base, C₃~ C₆Cycloalkyl group, C₃~ C₆Halo cycloa
Rukiru group, C_Four~ C₇Cycloalkylalkyl group, C₂~
C₆Alkoxyalkyl group, C₂~ C₆Alkyl thioal
Kill group, C₂~ C₆Alkoxycarbonylalkyl group, C
₂~ C₆Cyanoalkyl group, C₁~ C₆Alkoxy group, C₁
~ C₆Haloalkoxy group, C₂~ C₆Alkenyloxy
Base, C₂~ C₆Haloalkenyloxy group, C₂~ C₆Archi
Nyloxy group, C₂~ C₆Haloalkynyloxy group, C₃
~ C₆Cycloalkyloxy group, C₃~ C₆Halo cycloa
Rualkyloxy group, C_Four~ C₇Cycloalkyl alkyl oki
Shi group, C₂~ C₆Alkoxyalkyloxy group, C₂~ C₆
Alkylthioalkyloxy group, C₃~ C₆Alkoxyca
Rubonylalkyloxy group, C₂~ C₆Cyanoalkyl
Xy group, C₁~ C₆Alkylthio group, C₁~ C₆Halo Archi
Ruthio group, C₂~ C₆Alkenylthio group, C₂~ C₆Haloa
Lucenylthio group, C₂~ C₆Alkynylthio group, C₂~ C₆
Haloalkynylthio group, C₃~ C₆Cycloalkylthio
Base, C₃~ C₆Halocycloalkylthio group, C_Four~ C₇Shiku
Roalkylalkylthio group, C₂~ C₆Alkoxy alk
Ruthio group, C₂~ C₆Alkylthio alkylthio group, C₂
~ C₆Alkoxycarbonylalkylthio group, C₂~ C₆
Cyanoalkylthio group, C₁~ C₆Alkylsulfinyl
Base, C₁~ C₆Haloalkylsulfinyl group, C₂~ C₆A
Lucenylsulfinyl group, C₂~ C₆Haloalkenyl sul
Finyl group, C₂~ C₆Alkynylsulfinyl group, C₂
~ C₆Haloalkynylsulfinyl group, C₃~ C₆Cyclo
Alkylsulfinyl group, C₃~ C₆Halocycloalkyl
Sulfinyl group, C_Four~ C₇Cycloalkyl alkyl sul
Finyl group, C₂~ C₆Alkoxyalkyl sulfinyl
Base, C₂~ C₆Alkylthioalkylsulfinyl group, C
₁~ C₆Alkylsulfonyl group, C₁~ C₆Haloalkyls
Ruphonyl group, C₂~ C₆Alkenylsulfonyl group, C₂~
C₆Haloalkenylsulfonyl group, C₂~ C₆Alkynyl
Sulfonyl group, C₂~ C₆A haloalkynylsulfonyl group,
C₃~ C₆Cycloalkylsulfonyl group, C₃~ C₆Haroshi
Chloroalkylsulfonyl group, C_Four~ C₇Cycloalkyl
Rukylsulphonyl group, C₂~ C₆Alkoxyalkyl sulphate
Honyl group, C₂~ C₆Alkylthioalkylsulfonyl
Base, C₂~ C₆Alkoxycarbonylalkylsulfonyl
Base, C₂~ C₆Cyanoalkylsulfonyl group, C₁~ C₆A
Rukylsulphonyloxy group, C₁~ C₆Haloalkyl sul
Honyloxy group, C₃~ C₆Cycloalkylsulfonyl
Xy group, C₃~ C₆Halocycloalkylsulfonyloxy
Base, C₂~ C₆Cyanoalkylsulfonyloxy group, C₂
~ C₇Alkylcarbonyloxy group, C₂~ C₇Halo al
Killcarbonyloxy group, C_Four~ C₇Cycloalkylcal
Bonyloxy group, C_Four~ C₇Halocycloalkylcarboni
Luoxy group, C ₃~ C₇Cyanoalkylcarbonyloxy
Base, C₂~ C₇Alkylcarbonyl group, C ₂~ C₇Halo al
Killcarbonyl group, C_Four~ C₇Cycloalkyl carbonyl
Base, C_Four~ C₇Halocycloalkylcarbonyl group, C₃~
C₇Cyanoalkylcarbonyl group, C₂~ C₇Alkoxy
Carbonyl group, C₂~ C₇A haloalkoxycarbonyl group,
C _Four~ C₇Cycloalkyloxycarbonyl group, C_Four~ C₇
Halocycloalkyloxycarbonyl group, C₃~ C₇Shea
Noalkyloxycarbonyl group, Mono C₁~ C₆Alkyl
Aminocarbonyl group, Mono C₁~ C₆Haloalkylamino
Carbonyl group, di-C ₁~ C₆Alkylaminocarbonyl
Group, di-C₁~ C₆Haloalkylaminocarbonyl group, mono
C₁~ C₆Alkylaminosulfonyl group, Mono C₁~ C₆Ha
Roalkylaminosulfonyl group, di-C₁~ C₆Alkyla
Minosulfonyl group, di-C₁~ C₆Haloalkylaminosul
Sulfonyl group, aminocarbonyl group, aminosulfonyl group,
Formylamino group, C₂~ C₇Alkylcarbonylamino
Base, C₂~ C₇Haloalkylcarbonylamino group, amino
Group, Mono C₁~ C₆Alkylamino group, Mono C₁~ C₆Halo
Alkylamino group, di-C₁~ C₆Alkylamino group, di-C
₁~ C₆Haloalkylamino group, formed between adjacent carbon atoms
Formed -CH = CH-CH = CH- group, -OCH₂O-
Group, -OCH₂CH₂O-group, -OCF₂O-group, -OC
F₂CF₂O-group, -OCF₂CF₂-Group, substituted
Optionally phenyl group, optionally substituted phenoxy
Group, optionally substituted phenylthio group, substituted
Phenylsulfinyl group which may be present, which may be substituted
Good phenylsulfonyl group, optionally substituted phenyl
Nylsulfonyloxy group, optionally substituted phenyl
Lucarbonyloxy group, optionally substituted phenyl
Carbonyl group, optionally substituted phenoxycarbo
Nyl group, optionally substituted phenylaminocarbonyl
Group, optionally substituted phenylsulfonylamino
Group, optionally substituted phenylcarbonylamino
Group, optionally substituted phenylamino group, substituted
Optionally substituted benzyl group, optionally substituted benzyl
Ruoxy group, optionally substituted benzylthio group,
Optionally substituted benzylsulfinyl group, substituted
Optionally substituted benzylsulfonyl group, optionally substituted
Good benzylsulfonyloxy group, optionally substituted
A benzylcarbonyloxy group, which may be substituted
Benzylcarbonyl group, optionally substituted benzyl
Oxycarbonyl group, optionally substituted benzyl group
Minocarbonyl group, optionally substituted benzylsul
Fonylamino group, optionally substituted benzylcarbo
Nylamino group, optionally substituted benzylamino
Group, optionally substituted pyridyl group, optionally substituted
Optionally pyridyloxy group, optionally substituted pyridi
Ruthio group, optionally substituted pyridylsulfinyl
Group, optionally substituted pyridylsulfonyl group, substituted
Optionally substituted pyridylsulfonyloxy group, substituted
Optionally substituted pyridylcarbonyloxy group, substituted
Optionally substituted pyridylcarbonyl group, optionally substituted
Good pyridyloxycarbonyl group, which may be substituted
A pyridylaminocarbonyl group, which may be substituted
Pyridylsulfonylamino group, optionally substituted
Lysylcarbonylamino group or optionally substituted
Pyridylamino group (provided that it may be substituted
As a halogen atom, hydroxyl group, cyano group, nitro
Base, C₁~ C₆Alkyl group, C ₁~ C₆Haloalkyl group, C
₁~ C₆Alkylthio group, C₁~ C₆A haloalkylthio group,
C₁~ C₆Alkylsulfonyl group, C₁~ C₆Haloalkyl
Sulfonyl group, C₁~ C₆Alkoxycarbonyl group, ami
Group or di-C₁~ C₆Alkylamino groups include
It ) Is mentioned.

X is preferably a halogen atom or C ₁
To C ₆ alkyl group, C _{1 to} C ₆ haloalkyl group, C _{1 to} C ₆
Haloalkoxy group, C _{1 to} C ₆ haloalkylthio group, C ₁
To C ₆ haloalkylsulfonyloxy groups.

Y is preferably a halogen atom, a cyano group, a nitro group, a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ haloalkyl group, a C ₁ -C ₆ alkoxy group, a C ₁ -C ₆ haloalkoxy group, C ₁ -C ₆ alkylthio group, C ₁ -C ₆ haloalkylthio group, C ₁ -C ₆ alkylsulfonyl group, C ₁ -C ₆ haloalkylsulfonyl group, C ₁ -C ₆ haloalkylsulfonyl group, the adjoining carbon atoms Formed between -OCF
₂ O- group or -OCF ₂ CF ₂ O- group.

Z is preferably a halogen atom, a cyano group, a nitro group, a C ₁ -C ₆ haloalkyl group, a C ₁ -C ₆ haloalkoxy group, a C ₁ -C ₆ alkylthio group or a C ₁ -C ₆ haloalkylthio group. A C ₁ -C ₆ alkylsulfinyl group,
A C ₁ -C ₆ haloalkylsulfinyl group, a C ₁ -C ₆ alkylsulfonyl group, a C ₁ -C ₆ haloalkylsulfonyl group,
C ₁ -C ₆ alkylsulfonyloxy group, C ₁ -C ₆ haloalkylsulfonyl group, next there was -OCF ₂ O-group formed between carbon atoms, -OCF ₂ CF ₂ O- group or a -
OCF ₂ CF ₂ - group.

R¹Is a halogen atom, hydroxyl group,
Ano group, nitro group, C₁~ C₆Alkyl group, C₁~ C₆Halo
Alkyl group, C₁~ C₆Alkoxy group, C₁~ C₆Halo al
Coxy group, C₁~ C₆Alkylthio group, C₁~ C₆Halo al
Kirthio group, C₁~ C₆Alkylsulfonyl group, C₁~ C₆
Haloalkylsulfonyl group, C₂~ C₆Alkoxy carbo
Nyl group, amino group, di-C₁~ C₆Alkylamino group or
An optionally substituted phenyl group (provided that it is substituted
The substituents that may be present include halogen atoms, hydroxyl groups, and
Ano group, nitro group, C₁~ C₆Alkyl group, C₁~ C₆Halo
Alkyl group, C ₁~ C₆Alkoxy group, C₁~ C₆Halo al
Coxy group, C₁~ C₆Alkylthio group, C ₁~ C₆Halo al
Kirthio group, C₁~ C₆Alkylsulfonyl group, C₂~ C₆
Alkoxycarbonyl group, amino group or di-C₁~ C₆A
Includes a rualkylamino group).

R ¹ is preferably a hydrogen atom or C ₁
To C ₆ alkyl groups.

R ² , R ³ and R ⁴ are a hydrogen atom, C ₁
-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 alkoxyalkyl group, C ₂ -C ₆ alkylcarbonyl group, C ₂
To C ₆ alkoxycarbonyl group, C _{2 to} C ₆ haloalkylcarbonyl group, C _{1 to} C ₆ alkylthio group, C _{1 to} C ₆ haloalkylthio group, C _{2 to} C ₁₂ dialkylaminothio group,
A C ₃ -C ₁₂ (alkyl) alkoxycarbonylaminothio group or an optionally substituted benzyl group (provided that
As the substituent which may be substituted, a halogen atom,
Hydroxyl group, cyano group, nitro group, C ₁ -C ₆ alkyl group, C
₁ -C ₆ haloalkyl group, C ₁ -C ₆ alkoxy group, C ₁ ~
C ₆ haloalkoxy group, C _{1 to} C ₆ alkylthio group, C ₁ to
C ₆ haloalkylthio group, C ₁ -C ₆ alkylsulfonyl group, C ₂ -C ₆ alkoxycarbonyl group, amino group or di C ₁ -C ₆ alkylamino group).

R ² , R ³ and R ⁴ are preferably a hydrogen atom or a C ₁ -C ₆ alkyl group.

L is preferably an integer of 0 to 2.

M is preferably an integer of 0-2.

N is preferably an integer of 1 to 3.

Among the compounds included in the present invention, the compounds having an asymmetric carbon atom include the optically active compounds (+) and (−). Further, when there are configurational isomers, cis isomers and trans isomers are included. Further, when R ² is a hydrogen atom, the compound of the present invention may have the following tautomers, and the structures thereof are also included.

[0029]

[Chemical 3]

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 Q7 in Table 1 are groups represented by the following formula.

[0032]

[Chemical 4]

Table 1

[0034]

[Chemical 5]

[0035]

[Table 1] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 HHHO 3-F 4-F 2-F 0 HHHO 3-F 4-F 3-F 0 HHHO 3-F 4-F 4-F 0 HHHO 3-F 4-F 2-Cl 0 HHHO 3-F 4-F 3-Cl 0 HHHO 3-F 4-F 4-Cl 0 HHHO 3-F 4-F 3-Br 0 HHHO 3-F 4-F 4-Br 0 HHHO 3-F 4-F 4-I 0 HHHO 3-F 4-F 4-CH ₃ 0 HHHO 3-F 4-F 4-CH ₂ CH ₃ 0 HHHO 3-F 4-F 4-CH (CH ₃ ) ₂₀ HHHO 3-F 4-F 4-CH ₂ CH ₂ CH ₂ CH ₃ 0 HHHO 3- F 4-F 4-C (CH ₃ ) ₃ 0 HHHO 3-F 4-F 4-CH ₂ CH = CH ₂ 0 HHHO 3-F 4-F 4-C ≡ CH 0 HHHO 3-F 4-F 4 -CH ₂ C ≡ CH 0 HHHO 3-F 4-F 4-Q1 0 HHHO 3-F 4-F 4-Q2 0 HHHO 3-F 4-F 4-Q3 0 HHHO 3-F 4-F 4-Q4 0 HHHO 3-F 4-F 4-CHF ₂ 0 HHHO 3-F 4-F 4-CH ₂ Br ────────────────────────── ──────────

[0036]

[Table 2] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 HHHO 3-F 4-F 4-CH ₂ Cl 0 HHHO 3-F 4-F 2-CF ₃ 0 HHHO 3-F 4-F 3-CF ₃ 0 HHHO 3-F 4-F 4-CF ₃ 0 HHHO 3-F 4-F 4-CH ₂ CH = CHCl 0 HHHO 3-F 4-F 4-CH = C (Cl) CF ₃ 0 HHHO 3-F 4-F 4-CH ₂ C ≡ CBr 0 HHHO 3-F 4-F 4- (Q4-1-Cl ) 0 HHHO 3-F 4-F 4-CH ₂ CN 0 HHHO 3-F 4-F 4-CH ₂ CH (CH ₃ ) CN 0 HHHO 3-F 4-F 4-CH ₂ OH 0 HHHO 3-F 4-F 4-CH ₂ CO ₂ H 0 HHHO 3-F 4-F 4-OCH ₃ 0 HHHO 3-F 4-F 4-OCH ₂ CH ₃ 0 HHHO 3-F 4-F 4-OCH (CH ₃ ) ₂ 0 HHHO 3-F 4-F 4-OC (CH ₃ ) ₃ 0 HHHO 3-F 4-F 4-OCH ₂ CH = CH ₂ 0 HHHO 3-F 4-F 4-OCH ₂ C ≡ CH 0 HHHO 3-F 4-F 4-O (Q4) 0 HHHO 3-F 4-F 4-OCHF ₂ 0 HHHO 3-F 4-F 4-OCF ₂ Br 0 HHHO 3-F 4-F 2-OCF ₃ 0 HHHO 3-F 4-F 3-OCF ₃ ────────────────────────────────────

[0037]

[Table 3] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 HHHO 3-F 4-F 4-OCF ₃ 0 HHHO 3-F 4-F 4-OCH ₂ CF ₃ 0 HHHO 3-F 4-F 4-OCF ₂ CF ₃ 0 HHHO 3-F 4-F 4-OCF ₂ CHF ₂ 0 HHHO 3-F 4-F 4 -OCF ₂ CHCl ₂ 0 HHHO 3-F 4-F 4-OCF ₂ CHFCl 0 HHHO 3-F 4-F 4-OCF ₂ CHFBr 0 HHHO 3-F 4-F 4-0CF ₂ CF ₂ CF ₃ 0 HHHO 3 -F 4-F 4-OCH ₂ CH = CHCl 0 HHHO 3-F 4-F 4-OCH ₂ C ≡ CBr 0 HHHO 3-F 4-F 4-O (Q4-2,2-Cl ₂ ) 0 HHHO 3-F 4-F 4-SCH ₃₀ HHHO 3-F 4-F 4-SCH ₂ CH = CH ₂₀ HHHO 3-F 4-F 4-SCH ₂ C ≡ CH 0 HHHO 3-F 4-F 4 -S (Q4) 0 HHHO 3-F 4-F 4-SCHF ₂ 0 HHHO 3-F 4-F 4-SCF ₂ Br 0 HHHO 3-F 4-F 4-SCF ₃ 0 HHHO 3-F 4-F 4-SOCH ₃ 0 HHHO 3-F 4-F 4-SOCH ₂ CH = CH ₂ 0 HHHO 3-F 4-F 4-S0CH ₂ C ≡ CH 0 HHHO 3-F 4-F 4-S0 (Q4) 0 HHHO 3-F 4-F 4-SOCF ₃ ────────────────────────────────────

[0038]

[Table 4] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 HHHO 3-F 4-F 4-SO ₂ CH ₃ 0 HHHO 3-F 4-F 4-SO ₂ CH ₂ CH = CH ₂ 0 HHHO 3-F 4-F 4-S0 ₂ CH ₂ C ≡ CH 0 HHHO 3-F 4-F 4-S0 ₂ (Q4 ) 0 HHHO 3-F 4-F 4-SO ₂ CF ₃ 0 HHHO 3-F 4-F 4-CH ₂ OCH ₃ 0 HHHO 3-F 4-F 4-OCH ₂ CH ₂ OCH ₃ 0 HHHO 3-F 4-F 4-CH ₂ OCH ₂ CF ₃ 0 HHHO 3-F 4-F 4-OCF ₂ CHFOCF ₃ 0 HHHO 3-F 4-F 4-CH ₂ SCH ₃ 0 HHHO 3-F 4-F 4-OCH ₂ CH ₂ SCH ₃ 0 HHHO 3-F 4-F 4-CH ₂ CO ₂ CH ₃ 0 HHHO 3-F 4-F 4-CH ₂ CO ₂ CH ₂ CF ₃ 0 HHHO 3-F 4-F 4-CH ₂ COCH ₃ 0 HHHO 3-F 4-F 4-OCO ₂ CH ₃ 0 HHHO 3-F 4-F 4-OCOCH ₃ 0 HHHO 3-F 4-F 4-COCH ₃ 0 HHHO 3-F 4-F 4 -COCH ₂ CH = CH ₂ 0 HHHO 3-F 4-F 4-C0CH ₂ C ≡ CH 0 HHHO 3-F 4-F 4-CO (Q3) 0 HHHO 3-F 4-F 4-COCF ₃ 0 HHHO 3-F 4-F 4- CO 2 CH 2 CH 3 0 HHHO 3-F 4-F 4-CO 2 C (CH 3) 3 ────────────────── ────────────────

[0039]

[Table 5] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 HHHO 3-F 4-F 4-CO ₂ CH ₂ CF ₃ 0 HHHO 3-F 4-F 4-OCH ₂ CO ₂ CH ₃ 0 HHHO 3-F 4-F 4-NO ₂ 0 HHHO 3-F 4-F 4-CN 0 HHHO 3-F 4-F 4-OH 0 HHHO 3-F 4-F 4-CO ₂ H 0 HHHO 3-F 4-F 4-SCN 0 HHHO 3-F 4-F 4-OSO ₂ CH ₃ 0 HHHO 3-F 4-F 4 -CSCH ₃ 0 HHHO 3-F 4-F 4-NH ₂ 0 HHHO 3-F 4-F 4-N (CH ₃ ) ₂₀ HHHO 3-F 4-F 4-N (CH ₃ ) CH ₂ CH ₃ 0 HHHO 3-F 4-F 4-N (CH ₃ ) CH ₂ CH = CH ₂ 0 HHHO 3-F 4-F 4-N (CH ₃ ) CH ₂ C≡CH 0 HHHO 3-F 4-F 4 _{-N (CH 3) CH 2 C} 6 H 5 0 HHHO 3-F 4-F 4-CON (CH 3) 2 0 HHHO 3-F 4-F 4-0CON (CH 3) 2 0 HHHO 3-F 4 -F 4-NHCOCH ₃ 0 HHHO 3-F 4-F 4-NHCSCH ₃ 0 HHHO 3-F 4-F 4-SO ₂ N (CH ₃ ) ₂ 0 HHHO 3-F 4-F 4-Si (CH ₃ ) ₃₀ HHHO 3-F 4-F 4-C ₆ H ₅ 0 HHHO 3-F 4-F 4- (C ₆ H ₄ -4-Cl) ─────────────── ──────────────── ────

[0040]

[Table 6] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 HHHO 3-F 4-F 4-OC ₆ H ₅ 0 HHHO 3-F 4-F 4-O (C ₆ H ₄ -4-CF ₃ ) 0 HHHO 3-F 4-F 4-O (C ₆ H ₄ -4-OCF ₃ ) 0 HHHO 3-F 4-F 4-O (C ₆ H ₃ -2,4-F ₂ ) 0 HHHO 3-F 4-F 4-O (C ₆ H ₃ -3,5-Cl ₂ ) 0 HHHO 3-F 4- F 3-O (C ₆ H ₄ -4-CF ₃ ) 0 HHHO 3-F 4-F 4-S (C ₆ H ₃ -2-Cl-4-CF ₃ ) 0 HHHO 3-F 4-F 4 _{-SO 2 C 6 H 5 0 HHHO} 3-F 4-F 4-NH (C 6 H 3 -2-Cl-4-CF 3) 0 HHHO 3-F 4-F 4-N (CH 2 CH 3) (C ₆ H ₄ -4-Cl) 0 HHHO 3-F 4-F 4-CH ₂ C ₆ H ₅ 0 HHHO 3-F 4-F 4-CF ₂ (C ₆ H ₄ -4-Br) 0 HHHO 3-F 4-F 4-COC ₆ H ₅ 0 HHHO 3-F 4-F 4-OCH ₂ (C ₆ H ₄ -4-CF ₃ ) 0 HHHO 3-F 4-F 4-CH ₂ OC ₆ H _{5 0 HHHO 3-F 4-} F 4-NHCH 2 C 6 H 5 0 HHHO 3-F 4-F 4-CH 2 CH 2 C 6 H 5 0 HHHO 3-F 4-F 4-CH = CH (C ₆ H ₃ -2,4-Cl ₂ ) 0 HHHO 3-F 4-F 4-N = NC ₆ H ₅ 0 HHHO 3-F 4-F 4-OCH ₂ CH ₂ C ₆ H ₅ 0 HHHO 3-F 4-F 4-NHCON (CH ₃ ) ( C ₆ H ₄ -4-Cl) 0 HHHO 3-F 4-F 4-OCH ₂ CH ₂ OC ₆ H ₅ 0 HHHO 3-F 4-F 4-NHCSNHC ₆ H ₅ ────────── ─────────────────────────

[0041]

[Table 7] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 HHHO 3-F 4-F 2,4-F ₂₀ HHHO 3-F 4-F 3,5-F ₂₀ HHHO 3-F 4-F 2,3-Cl ₂₀ HHHO 3-F 4-F 2,4-Cl ₂₀ HHHO 3-F 4- F 2,5-Cl ₂ 0 HHHO 3-F 4-F 2,6-Cl ₂ 0 HHHO 3-F 4-F 3,4-Cl ₂ 0 HHHO 3-F 4-F 3,5-Cl ₂ 0 HHHO 3-F 4-F 3,4-Br ₂ 0 HHHO 3-F 4-F 2,4-I ₂ 0 HHHO 3-F 4-F 2,4- (CH ₃ ) ₂ 0 HHHO 3-F 4 -F 3,4- (OCH ₃ ) ₂₀ HHHO 3-F 4-F 2-F-4-Cl 0 HHHO 3-F 4-F 2-F-4-Br 0 HHHO 3-F 4-F 2 -F-4-OCH (CH ₃ ) ₂₀ HHHO 3-F 4-F 2-F-4-OCHF ₂₀ HHHO 3-F 4-F 2-F-4-OCF ₃ 0 HHHO 3-F 4- F 2-F-4-OCF ₂ CHF ₂₀ HHHO 3-F 4-F 2-F-4-OCF ₂ CHFCl 0 HHHO 3-F 4-F 2-F-4-OCF ₂ CHFCF ₃ 0 HHHO 3- F 4-F 2-F-4-OCF ₂ CHFOCF ₃ 0 HHHO 3-F 4-F 2-F-4-SO ₂ CF ₂ CHFCl 0 HHHO 3-F 4-F 2-F-4-O (C ₆ H ₄ -4-Cl) ──────────────────────────────────

[0042]

[Table 8] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 HHHO 3-F 4-F 2-F-4 -O (Q5-3-Cl-5-CF ₃ ) 0 HHHO 3-F 4-F 3-F-4-O (Q5-3-Cl-5-CF ₃ ) 0 HHHO 3-F 4-F 2 -Cl-4-CF ₃ 0 HHHO 3-F 4-F 2-Cl-4-SCF ₂ CHF ₂₀ HHHO 3-F 4-F 3-Cl-4-CF ₃ 0 HHHO 3-F 4-F 3 _{-F-4-OCF 3 0 HHHO} 3-F 4-F 3-Cl-4-OCF 3 0 HHHO 3-F 4-F 3-Cl-4-OCHF 2 0 HHHO 3-F 4-F 3-Cl -4-OCF ₂ CHF ₂ 0 HHHO 3-F 4-F 3-Cl-4-OCF ₂ CHFOCF ₃ 0 HHHO 3-F 4-F 3-Cl-4-SCHF ₂ 0 HHHO 3-F 4-F 3 -Cl-4-CO ₂ CH ₃ 0 HHHO 3-F 4-F 3-Cl-4-CO ₂ CH (CH ₂ F) ₂ 0 HHHO 3-F 4-F 3-Cl-4-O (C ₆ H ₄ -4-CF ₃ ) 0 HHHO 3-F 4-F 3-Cl-4-O (Q5-5-CF ₃ ) 0 HHHO 3-F 4-F 3-Cl-4-NH (Q5-5 -CF ₃ ) 0 HHHO 3-F 4-F 3-Br-4-OCF ₃ 0 HHHO 3-F 4-F 3-CH ₃ -4-OCF ₂ CHF ₂ 0 HHHO 3-F 4-F 3-CF ₃ -4-Cl 0 HHHO 3-F 4-F 3-CF ₃ -4-OCF ₂ CHF ₂₀ HHHO 3-F 4-F 3-CF ₃ -4-OCF ₂ CHFBr 0 HHHO 3-F 4-F 3,4- (CF ₃ ) ₂₀ HHHO 3-F 4- F 3,4- (OCF ₃ ) ₂ ────────────────────────────────────

[0043]

[Table 9] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 HHHO 3-F 4-F 2,3-F ₂ -4-OCF ₃ 0 HHHO 3-F 4-F 2,5-F ₂ -4-Cl 0 HHHO 3-F 4-F 2,5-F ₂ -4-Br 0 HHHO 3-F 4-F 2,5-F ₂ -4-OCF ₃ 0 HHHO 3-F 4-F 3,5-F ₂ -4-CF ₃ 0 HHHO 3-F 4-F 2,5-Cl ₂ -4-OCF ₂ CHF ₂ 0 HHHO 3-F 4-F 2,5-Cl ₂ -4-O (Q5-3,5-Cl ₂ ) 0 HHHO 3-F 4-F 2,6-Cl ₂ -4-CF ₃ 0 HHHO 3-F 4-F 2,3,4-F ₃ 0 HHHO 3-F 4-F 2,4,5-F ₃ 0 HHHO 3-F 4-F 2,3,4-Cl ₃ 0 HHHO 3- F 4-F 2,4,5-Cl ₃ 0 HHHO 3-F 4-F 2,4,6-Cl ₃ 0 HHHO 3-F 4-F 3,4,5-Cl ₃ 0 HHHO 3-F 4 -F 2-F-4,5-Cl ₂ 0 HHHO 3-F 4-F 3,5-Cl ₂ -4-O (Q5-5-CF ₃ ) 0 HHHO 3-F 4-F 3,5- Cl ₂ -4-O (C ₆ H ₄ -4-CF ₃ ) 0 HHHO 3-F 4-F 3,5-Cl ₂ -4-OCH ₂ CH = CH ₂ 0 HHHO 3-F 4-F 3, 5-Cl ₂ -4-OCF ₂ CHF ₂ 0 HHHO 3-F 4-F 3,5-Cl ₂ -4-OCF ₂ CHFOCF ₃ 0 HHHO 3-F 4-F 3,5-Cl ₂ -4-SCF ₂ CHF ₂ 0 HHHO 3-F 4-F 3,5-Cl ₂ -4-N (CH ₃ ) CH ₂ CH ₂ CH ₃ 0 HHHO 3-F 4-F 3,5-Cl ₂ -4-N (CH ₃ ) CH ₂ C ₆ H ₅ ─────────────────────── ─────────────

[0044]

[Table 10] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 HHHO 3-F 4-F 2-F-3 -CF ₃ -5-Cl 0 HHHO 3-F 4-F 2-F-4-OCF ₃ -5-Cl 0 HHHO 3-F 4-F 2-F-4-OCF ₂ CHF ₂ -5-Cl 0 HHHO 3-F 4-F 2-CF ₃ -4,6- (NO ₂ ) ₂ 0 HHHO 3-F 4-F 2,3,4,5-F ₄ 0 HHHO 3-F 4-F 2,3 , 5,6-F ₄₀ HHHO 3-F 4-F 2,3,4,5-Cl ₄ 0 HHHO 3-F 4-F 2,4-F ₂ -3,5-Cl ₂ 0 HHHO 3- F 4-F 2,6-F ₂ -3,5-Cl ₂ 0 HHHO 3-F 4-F 2,3,5-F ₃ -4-OCF ₃ 0 HHHO 3-F 4-F 2-F- 3,5-Cl ₂ -4-OCF ₂ CHF ₂ 0 HHHO 3-F 4-F 2,3,4,5,6-F ₅ 0 HHHO 3-F 4-F 2,3,5,6-F ₄ -4-CN 0 HHHO 3-F 4-F 2,4,6-F ₃ -3,5-Cl ₂ 0 HHHO 3-F 4-F 3-Cl-4-F 0 HHHO 3-F 4- F 4-OSO ₂ CF ₃ 0 HHHO 3-F 4-F 4- (Q1-2,2-Cl ₂ ) 0 HHHO 3-F 4-F 4-SO ₂ CF ₂ CF ₂ CF ₃ 0 HHHO 3-F 4-F 4-SOCF ₂ CHF ₂₀ HHHO 3-F 4-F 4-SO ₂ CHF ₂₀ HHHO 3-F 4-F 3-OCF ₂ O-4 0 HHHO 3-F 4-F 3-OCH ₂ O-4 0 HHHO 3-F 4-F 3-OCF 2 CF 2 O-4 ───── ─────────────────────────────

[0045]

[Table 11] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 HHHO 3-CF ₃ 4-F 4-F 0 HHHO 3-CF ₃ 4-F 3-Cl 0 HHHO 3-CF ₃ 4-F 4-Cl 0 HHHO 3-CF ₃ 4-F 4-Br 0 HHHO 3-CF ₃ 4-F 4-I 0 HHHO 3 -CF ₃ 4-F 4-CH ₃₀ HHHO 3-CF ₃ 4-F 4-C (CH ₃ ) ₃₀ HHHO 3-CF ₃ 4-F 4-CHF ₂ 0 HHHO 3-CF ₃ 4-F 3 -CF ₃₀ HHHO 3-CF ₃ 4-F 4-CF ₃₀ HHHO 3-CF ₃ 4-F 4-OCH ₃₀ HHHO 3-CF ₃ 4-F 4-OCH ₂ CH ₃₀ HHHO 3-CF ₃ 4-F 4-OCHF ₂ 0 HHHO 3-CF ₃ 4-F 4-OCF ₂ Br 0 HHHO 3-CF ₃ 4-F 3-OCF ₃ 0 HHHO 3-CF ₃ 4-F 4-OCF ₃ 0 HHHO 3 -CF ₃ 4-F 4-OCH ₂ CF ₃ 0 HHHO 3-CF ₃ 4-F 4-OCF ₂ CF ₃ 0 HHHO 3-CF ₃ 4-F 4-OCF ₂ CHF ₂₀ HHHO 3-CF ₃ 4- F 4-OCF ₂ CHFCl 0 HHHO 3-CF ₃ 4-F 4-0CF ₂ CF ₂ CF ₃ 0 HHHO 3-CF ₃ 4-F 4-SCH ₃ 0 HHHO 3-CF ₃ 4-F 4-SCHF ₂ ─ ──────────────────────────────────

[0046]

[Table 12] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 HHHO 3-CF ₃ 4-F 4-SCF ₂ Br 0 HHHO 3-CF ₃ 4-F 4-SCF ₃₀ HHHO 3-CF ₃ 4-F 4-SOCH ₃₀ HHHO 3-CF ₃ 4-F 4-SOCF ₃₀ HHHO 3-CF ₃ 4-F 4 -SO ₂ CH ₃ 0 HHHO 3-CF ₃ 4-F 4-SO ₂ CF ₃ 0 HHHO 3-CF ₃ 4-F 4-SO ₂ CF ₂ CHF ₂₀ HHHO 3-CF ₃ 4-F 4-OCO ₂ CH ₃ 0 HHHO 3-CF ₃ 4-F 4-OCF ₂ CHFOCF ₃ 0 HHHO 3-CF ₃ 4-F 4-OCOCH ₃ 0 HHHO 3-CF ₃ 4-F 4-COCH ₃ 0 HHHO 3-CF ₃ 4 -F 4-COCF ₃ 0 HHHO 3-CF ₃ 4-F 4-CO ₂ CH ₂ CH ₃ 0 HHHO 3-CF ₃ 4-F 4-CO ₂ CH ₂ CF ₃ 0 HHHO 3-CF ₃ 4-F 4 -NO ₂ 0 HHHO 3-CF ₃ 4-F 4-CN 0 HHHO 3-CF ₃ 4-F 4-OH 0 HHHO 3-CF ₃ 4-F 4-CO ₂ H 0 HHHO 3-CF ₃ 4-F 4-OSO ₂ CH ₃ 0 HHHO 3-CF ₃ 4-F 4-OSO ₂ CF ₃ 0 HHHO 3-CF ₃ 4-F 4-N (CH ₃ ) ₂ 0 HHHO 3-CF ₃ 4-F 4-Si _{(CH 3) 3 0 HHHO 3} -CF 3 4-F 4-C 6 H 5 ─────────────────────── ───────────

[0047]

[Table 13] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 HHHO 3-CF ₃ 4-F 4-OC ₆ H ₅ 0 HHHO 3-CF ₃ 4-F 4-O (C ₆ H ₄ -4-CF ₃ ) 0 HHHO 3-CF ₃ 4-F 4-O (Q5-5-CF ₃ ) 0 HHHO 3-CF _{3 4-F 4-SO 2} C 6 H 5 0 HHHO 3-CF 3 4-F 4-CH 2 C 6 H 5 0 HHHO 3-CF 3 4-F 4-COC 6 H 5 0 HHHO 3-CF 3 4-F 2,4-F ₂₀ HHHO 3-CF ₃ 4-F 3,4-Cl ₂ 0 HHHO 3-CF ₃ 4-F 3,4-Br ₂₀ HHHO 3-CF ₃ 4-F 2- F-4-Cl 0 HHHO 3-CF ₃ 4-F 2-F-4-OCF ₃ 0 HHHO 3-CF ₃ 4-F 2-F-4-OCF ₂ CHF ₂₀ HHHO 3-CF ₃ 4-F 3-Cl-4-CF ₃ 0 HHHO 3-CF ₃ 4-F 3-F-4-OCF ₃ 0 HHHO 3-CF ₃ 4-F 2-F-4-OCF ₂ CHF ₂ 0 HHHO 3-CF ₃ 4-F 3-Cl-4-OCF ₂ CHFOCF ₃ 0 HHHO 3-CF ₃ 4-F 3-Cl-4-SCHF ₂₀ HHHO 3-CF ₃ 4-F 2,5-F ₂ -4-OCF ₃ 0 HHHO 3-CF ₃ 4-F 2-F-4,5-Cl ₂ 0 HHHO 3-CF ₃ 4-F 3,5-Cl ₂ -4-OCF ₂ CHF ₂ 0 HHHO 3-CF ₃ 4-F 3,4,5-Cl ₃ 0 HHHO 3-CF ₃ 4-F 2-F-4-OCF ₂ CHF ₂ -5-Cl 0 HHHO 3-CF ₃ 4-F 2,4-F ₂ -3,5-Cl ₂ ────────────────────────────────────

[0048]

[Table 14] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 HHHO 3-Cl 4-F 4-Cl 0 HHHO 3-Cl 4-F 4-Br 0 HHHO 3-Cl 4-F 4-CF ₃ 0 HHHO 3-Cl 4-F 4-OCH ₂ CH ₃ 0 HHHO 3-Cl 4-F 4-OCHF ₂₀ HHHO 3 -Cl 4-F 4-OCF ₂ Br 0 HHHO 3-Cl 4-F 4-OCF ₂ CHF ₂ 0 HHHO 3-Cl 4-F 4-OCF ₃ 0 HHHO 3-Cl 4-F 4-SCHF ₂₀ HHHO 3-Cl 4-F 4-SCF ₂ Br 0 HHHO 3-Cl 4-F 4-SCF ₃ 0 HHHO 3-Cl 4-F 4-O (Q6-6-Cl) 0 HHHO 3-Cl 4-F 4 -O (Q7) 0 HHHO 3-Cl 4-F 4-O (Q5-5-CF ₃ ) 0 HHHO 3-Cl 4-F 4-OCF ₂ CHFOCF ₃ 0 HHHO 3-Cl 4-F 4-COCF ₃ 0 HHHO 3-Cl 4-F 4-CO ₂ CH ₂ CH ₃ 0 HHHO 3-Cl 4-F 4-NO ₂ 0 HHHO 3-Cl 4-F 4-CN 0 HHHO 3-Cl 4-F 4-OSO ₂ CF ₃ 0 HHHO 3-Cl 4-F 3,4-Cl ₂ 0 HHHO 3-Cl 4-F 3-Cl-4-OCF ₂ CHF ₂ 0 HHHO 3-Cl 4-F 2,4-F _2- 3,5-Cl ₂ ────────────────────────────────────

[0049]

[Table 15] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 HHHOHH 4-Cl 0 HHHOHH 4-Br 0 HHHOHH 4 -CF ₃ 0 HHHOHH 4-OCHF ₂ 0 HHHOHH 4-OCF ₂ Br 0 HHHOHH 4-OCF ₂ CHF ₂ 0 HHHOHH 4-OCF ₃ 0 HHHOHH 4-SCF ₃ 0 HHHOHH 4-OSO ₂ CF ₃ 0 HHHOHH 3,4- Cl ₂ 0 HHHOH 4-F 4-Cl 0 HHHOH 4-F 4-Br 0 HHHOH 4-F 4-CF ₃ 0 HHHOH 4-F 4-OCHF ₂ 0 HHHOH 4-F 4-OCF ₂ Br 0 HHHOH 4- F 4-OCF ₂ CHF ₂₀ HHHOH 4-F 4-OCF ₃ 0 HHHOH 4-F 4-SCF ₃ 0 HHHOH 4-F 4-OSO ₂ CF ₃ 0 HHHOH 4-F 3,4-Cl ₂ 0 HHHOH 4 -CN 4-Cl 0 HHHOH 4-CN 4-Br 0 HHHOH 4-CN 4-CF ₃ ───────────────────────────── ───────

[0050]

[Table 16] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 HHHOH 4-CN 4-OCHF ₂ 0 HHHOH 4- CN 4-OCF ₂ Br 0 HHHOH 4-CN 4-OCF ₂ CHF ₂ 0 HHHOH 4-CN 4-OCF ₃ 0 HHHOH 4-CN 4-SCF ₃ 0 HHHOH 4-CN 4-OSO ₂ CF ₃ 0 HHHOH 4- CN 3,4-Cl ₂ 0 HHHOH 4-Cl 4-Cl 0 HHHOH 4-Cl 4-Br 0 HHHOH 4-Cl 4-CF ₃ 0 HHHOH 4-Cl 4-OCHF ₂ 0 HHHOH 4-Cl 4-OCF ₂ Br 0 HHHOH 4-Cl 4-OCF ₂ CHF ₂ 0 HHHOH 4-Cl 4-OCF ₃ 0 HHHOH 4-Cl 4-SCF ₃ 0 HHHOH 4-Cl 4-OSO ₂ CF ₃ 0 HHHOH 4-Cl 3,4- Cl ₂ 0 HHHOH 4-CF ₃ 4-Cl 0 HHHOH 4-CF ₃ 4-Br 0 HHHOH 4-CF ₃ 4-CF ₃ 0 HHHOH 4-CF ₃ 4-OCHF ₂ 0 HHHOH 4-CF ₃ 4-OCF ₂ Br 0 HHHOH 4-CF ₃ 4-OCF ₂ CHF ₂ ───────────────────────────────────

[0051]

[Table 17] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 HHHOH 4-CF ₃ 4-OCF ₃ 0 HHHOH 4 -CF ₃ 4-SCF ₃ 0 HHHOH 4-CF ₃ 4-OSO ₂ CF ₃ 0 HHHOH 4-CF ₃ 3,4-Cl ₂ 0 HHHOH 4-OSO ₂ CF ₃ 4-Cl 0 HHHOH 4-OSO ₂ CF ₃ 4-Br 0 HHHOH 4-OSO ₂ CF ₃ 4-CF ₃ 0 HHHOH 4-OSO ₂ CF ₃ 4-OCHF ₂ 0 HHHOH 4-OSO ₂ CF ₃ 4-OCF ₂ Br 0 HHHO 3-F 4-OSO ₂ CF ₃ 4-OCF ₂ CHF ₂₀ HHHO 3-F 4-OSO ₂ CF ₃ 4-OCF ₃ 0 HHHO 3-F 4-OSO ₂ CF ₃ 4-SCF ₃₀ HHHO 3-F 4-OSO ₂ CF ₃ 4- OSO ₂ CF ₃ 0 HHHO 3-F 4-OSO ₂ CF ₃ 3,4-Cl ₂ 0 HHHO 3-F 4-Cl 4-Cl 0 HHHO 3-F 4-Cl 4-Br 0 HHHO 3-F 4- Cl 4-CF ₃ 0 HHHO 3-F 4-Cl 4-OCHF ₂ 0 HHHO 3-F 4-Cl 4-OCF ₂ Br 0 HHHO 3-F 4-Cl 4-OCF ₂ CHF ₂₀ HHHO 3-F 4 -Cl 4-OCF ₃ 0 HHHO 3-F 4-Cl 4-SCF ₃ 0 HHHO 3-F 4-Cl 4-OSO ₂ CF ₃ ─────────────────── ─────────────────

[0052]

[Table 18] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 HHHO 3-F 4-Cl 3,4-Cl ₂ 0 HHHO 3-F 4-OCF ₃ 4-Cl 0 HHHO 3-F 4-OCF ₃ 4-Br 0 HHHO 3-F 4-OCF ₃ 4-CF ₃ 0 HHHO 3-F 4-OCF ₃ 4-OCHF ₂ 0 HHHO 3-F 4-OCF ₃ 4-OCF ₂ Br 0 HHHO 3-F 4-OCF ₃ 4-OCF ₂ CHF ₂ 0 HHHO 3-F 4-OCF ₃ 4-OCF ₃ 0 HHHO 3-F 4- OCF ₃ 4-SCF ₃ 0 HHHO 3-F 4-OCF ₃ 4-OSO ₂ CF ₃ 0 HHHO 3-F 4-OCF ₃ 3,4-Cl ₂ 0 HHHO 3-F 4-OCHF ₂ 4-Cl 0 HHHO 3-F 4-OCHF ₂ 4-Br 0 HHHO 3-F 4-OCHF ₂ 4-CF ₃ 0 HHHO 3-F 4-OCHF ₂ 4-OCHF ₂₀ HHHO 3-F 4-OCHF ₂ 4-OCF ₂ Br 0 HHHO 3-F 4-OCHF ₂ 4-OCF ₂ CHF ₂ 0 HHHO 3-F 4-OCHF ₂ 4-OCF ₃ 0 HHHO 3-F 4-OCHF ₂ 4-SCF ₃ 0 HHHO 3-F 4-OCHF ₂ 4-OSO ₂ CF ₃ 0 HHHO 3-F 4-OCHF ₂ 3,4-Cl ₂ 0 HHHO 3-F 4-Br 4-Cl 0 HHHO 3-F 4-Br 4-Br ──────── ────────────────────────────

[0053]

[Table 19] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 HHHO 3-F 4-Br 4-CF ₃ 0 HHHO 3-F 4-Br 4-OCHF ₂₀ HHHO 3-F 4-Br 4-OCF ₂ Br 0 HHHO 3-F 4-Br 4-OCF ₂ CHF ₂ 0 HHHO 3-F 4-Br 4-OCF ₃ 0 HHHO 3-F 4-Br 4-SCF ₃ 0 HHHO 3-F 4-Br 4-OSO ₂ CF ₃ 0 HHHO 3-F 4-Br 3,4-Cl ₂ 0 HHHO 3-Br 4-F 4- Cl 0 HHHO 3-Br 4-F 4-Br 0 HHHO 3-Br 4-F 4-CF ₃ 0 HHHO 3-Br 4-F 4-OCHF ₂₀ HHHO 3-Br 4-F 4-OCF ₂ Br 0 HHHO 3-Br 4-F 4-OCF ₂ CHF ₂ 0 HHHO 3-Br 4-F 4-OCF ₃ 0 HHHO 3-Br 4-F 4-SCF ₃ 0 HHHO 3-Br 4-F 4-OSO ₂ CF ₃ 0 HHHO 3-Br 4-F 3,4-Cl ₂ 0 HHHO 3-OCHF ₂ 4-F 4-Cl 0 HHHO 3-OCHF ₂ 4-F 4-Br 0 HHHO 3-OCHF ₂ 4-F 4- CF ₃ 0 HHHO 3-OCHF ₂ 4-F 4-OCHF ₂₀ HHHO 3-OCHF ₂ 4-F 4-OCF ₂ Br ────────────────────── ──────────────

[0054]

[Table 20] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 HHHO 3-OCHF ₂ 4-F 4-OCF ₂ CHF ₂₀ HHHO 3-OCHF ₂ 4-F 4-OCF ₃ 0 HHHO 3-OCHF ₂ 4-F 4-SCF ₃ 0 HHHO 3-OCHF ₂ 4-F 4-OSO ₂ CF ₃ 0 HHHO 3-OCHF ₂ 4 -F 3,4-Cl ₂ 0 HHHO 3-OSO ₂ CF ₃ 4-F 4-Cl 0 HHHO 3-OSO ₂ CF ₃ 4-F 4-Br 0 HHHO 3-OSO ₂ CF ₃ 4-F 4-CF ₃ 0 HHHO 3-OSO ₂ CF ₃ 4-F 4-OCHF ₂ 0 HHHO 3-OSO ₂ CF ₃ 4-F 4-OCF ₂ Br 0 HHHO 3-OSO ₂ CF ₃ 4-F 4-OCF ₂ CHF ₂ 0 HHHO 3-OSO ₂ CF ₃ 4-F 4-OCF ₃ 0 HHHO 3-OSO ₂ CF ₃ 4-F 4-SCF ₃ 0 HHHO 3-OSO ₂ CF ₃ 4-F 4-OSO ₂ CF ₃ 0 HHHO 3- OSO ₂ CF ₃ 4-F 3,4-Cl ₂ 0 HHHO 3-OCF ₃ 4-F 4-Cl 0 HHHO 3-OCF ₃ 4-F 4-Br 0 HHHO 3-OCF ₃ 4-F 4-CF ₃ 0 HHHO 3-OCF ₃ 4-F 4-OCHF ₂ 0 HHHO 3-OCF ₃ 4-F 4-OCF ₂ Br 0 HHHO 3-OCF ₃ 4-F 4-OCF ₂ CHF ₂ 0 HHHO 3-OCF ₃ 4- F 4-OCF ₃ 0 HHHO 3-OCF ₃ 4-F 4-SCF ₃ ─────────────── ────────────────────

[0055]

[Table 21] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 HHHO 3-OCF ₃ 4-F 4-OSO ₂ CF ₃ 0 HHHO 3-OCF ₃ 4-F 3,4-Cl ₂ 0 HHHO 3-Cl 4-CN 4-Cl 0 HHHO 3-Cl 4-CN 4-Br 0 HHHO 3-Cl 4-CN 4-CF ₃ 0 HHHO 3-Cl 4-CN 4-OCHF ₂ 0 HHHO 3-Cl 4-CN 4-OCF ₂ Br 0 HHHO 3-Cl 4-CN 4-OCF ₂ CHF ₂ 0 HHHO 3-Cl 4-CN 4- OCF ₃ 0 HHHO 3-Cl 4-CN 4-SCF ₃ 0 HHHO 3-Cl 4-CN 4-OSO ₂ CF ₃ 0 HHHO 3-Cl 4-CN 3,4-Cl ₂ 0 HHHO 3-CF ₃ 4- CN 4-Cl 0 HHHO 3-CF ₃ 4-CN 4-Br 0 HHHO 3-CF ₃ 4-CN 4-CF ₃ 0 HHHO 3-CF ₃ 4-CN 4-OCHF ₂ 0 HHHO 3-CF ₃ 4- CN 4-OCF ₂ Br 0 HHHO 3-CF ₃ 4-CN 4-OCF ₂ CHF ₂₀ HHHO 3-CF ₃ 4-CN 4-OCF ₃ 0 HHHO 3-CF ₃ 4-CN 4-SCF ₃ 0 HHHO 3 -CF ₃ 4-CN 4-OSO ₂ CF ₃ 0 HHHO 3-CF ₃ 4-CN 3,4-Cl ₂ 0 HHHO 3-OCF ₂ CHF ₂ 4-F 4-Cl ────────── ──────────────────────────

[0056]

[Table 22] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 HHHO 3-OCF ₂ CHF ₂ 4-F 4- Br 0 HHHO 3-OCF ₂ CHF ₂ 4-F 4-CF ₃ 0 HHHO 3-OCF ₂ CHF ₂ 4-F 4-OCHF ₂ 0 HHHO 3-OCF ₂ CHF ₂ 4-F 4-OCF ₂ Br 0 HHHO 3 -OCF ₂ CHF ₂ 4-F 4-OCF ₂ CHF ₂ 0 HHHO 3-OCF ₂ CHF ₂ 4-F 4-OCF ₃ 0 HHHO 3-OCF ₂ CHF ₂ 4-F 4-SCF ₃ 0 HHHO 3-OCF ₂ CHF ₂ 4-F 4-OSO ₂ CF ₃ 0 HHHO 3-OCF ₂ CHF ₂ 4-F 3,4-Cl ₂ 0 HHHO 4-F 4-F 4-Cl 0 HHHO 4-F 4-F 4-Br 0 HHHO 4-F 4-F 4-CF ₃ 0 HHHO 4-F 4-F 4-OCHF ₂ 0 HHHO 4-F 4-F 4-OCF ₂ Br 0 HHHO 4-F 4-F 4-OCF ₂ CHF ₂₀ HHHO 4-F 4-F 4-OCF ₃₀ HHHO 4-F 4-F 4-SCF ₃₀ HHHO 4-F 4-F 4-OSO ₂ CF ₃ 0 HHHO 4-F 4-F 3,4 -Cl ₂ 0 HHHO 3-CN 4-F 4-Cl 0 HHHO 3-CN 4-F 4-Br 0 HHHO 3-CN 4-F 4-CF ₃ 0 HHHO 3-CN 4-F 4-OCHF ₂ ─ ───────────────────────────────────

[0057]

[Table 23] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 HHHO 3-CN 4-F 4-OCF ₂ Br 0 HHHO 3-CN 4-F 4-OCF ₂ CHF ₂ 0 HHHO 3-CN 4-F 4-OCF ₃ 0 HHHO 3-CN 4-F 4-SCF ₃ 0 HHHO 3-CN 4-F 4-OSO ₂ CF ₃ 0 HHHO 3-CN 4-F 3,4-Cl ₂ 0 HHHO 4-OCHF ₂ 4-F 4-Cl 0 HHHO 4-OCHF ₂ 4-F 4-Br 0 HHHO 4-OCHF ₂ 4-F 4 -CF ₃ 0 HHHO 4-OCHF ₂ 4-F 4-OCHF ₂ 0 HHHO 4-OCHF ₂ 4-F 4-OCF ₂ Br 0 HHHO 4-OCHF ₂ 4-F 4-OCF ₂ CHF ₂ 0 HHHO 4-OCHF ₂ 4-F 4-OCF ₃₀ HHHO 4-OCHF ₂ 4-F 4-SCF ₃ 0 HHHO 4-OCHF ₂ 4-F 4-OSO ₂ CF ₃ 0 HHHO 4-OCHF ₂ 4-F 3,4-Cl ₂ 0 HHHO 4-OCHF ₂ 4-F 4-Cl 0 HHHO 3-F 2,4-F ₂ 4-Br 0 HHHO 3-F 2,4-F ₂ 4-CF ₃ 0 HHHO 3-F 2,4 -F ₂ 4-OCHF ₂₀ HHHO 3-F 2,4-F ₂ 4-OCF ₂ Br 0 HHHO 3-F 2,4-F ₂ 4-OCF ₂ CHF ₂ 0 HHHO 3-F 2,4-F ₂ 4-OCF ₃ ──────────────────────────────────

[0058]

[Table 24] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 HHHO 3-F 2,4-F ₂ 4- SCF ₃ 0 HHHO 3-F 2,4-F ₂ 4-OSO ₂ CF ₃ 0 HHHO 3-F 2,4-F ₂ 3,4-Cl ₂ 0 HHHO 3-F 3,4-F ₂ 4-Cl 0 HHHO 3-F 3,4-F ₂ 4-Br 0 HHHO 3-F 3,4-F ₂ 4-CF ₃ 0 HHHO 3-F 3,4-F ₂ 4-OCHF ₂ 0 HHHO 3-F 3 , 4-F ₂ 4-OCF ₂ Br 0 HHHO 3-F 3,4-F ₂ 4-OCF ₂ CHF ₂ 0 HHHO 3-F 3,4-F ₂ 4-OCF ₃ 0 HHHO 3-F 3,4 -F ₂ 4-SCF ₃ 0 HHHO 3-F 3,4-F ₂ 4-OSO ₂ CF ₃ 0 HHHO 3-F 3,4-F ₂ 3,4-Cl ₂ 0 HHHO 3,4-F ₂ 4 -F 4-Cl 0 HHHO 3,4-F ₂ 4-F 4-Br 0 HHHO 3,4-F ₂ 4-F 4-CF ₃ 0 HHHO 3,4-F ₂ 4-F 4-OCHF ₂₀ HHHO 3,4-F ₂ 4-F 4-OCF ₂ Br 0 HHHO 3,4-F ₂ 4-F 4-OCF ₂ CHF ₂ 0 HHHO 3,4-F ₂ 4-F 4-OCF ₃ 0 HHHO 3 , 4-F ₂ 4-F 4-SCF ₃ 0 HHHO 3,4-F ₂ 4-F 4-OSO ₂ CF ₃ 0 HHHO 3,4-F ₂ 4-F 3,4-Cl ₂ ──── ───────────────────────────── ─

[0059]

[Table 25] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 HHHO 3-CF ₃ H 4-Cl 0 HHHO 3 -CF ₃ 2-F 4-CF ₃₀ HHHO 3-CF ₃ 3-F 4-OCF ₃₀ HHHO 3-CF ₃ 2-Cl 4-Cl 0 HHHO 3-CF ₃ 3-Cl 4-CF ₃₀ HHHO 3-CF ₃ 4-Cl 4-OCF ₃ 0 HHHO 3-CF ₃ 3-Br 4-Cl 0 HHHO 3-CF ₃ 4-Br 4-CF ₃ 0 HHHO 3-CF ₃ 3-I 4-OCF ₃ 0 HHHO 3-CF ₃ 4-I 4-Cl 0 HHHO 3-CF ₃ 4-CH ₃ 4-CF ₃ 0 HHHO 3-CF ₃ 4-CH ₂ CH ₃ 4-OCF ₃ 0 HHHO 3-CF ₃ 4-CH (CH ₃ ) ₂ 4-Cl 0 HHHO 3-CF ₃ 4-CH ₂ CH ₂ CH ₂ CH ₃ 4-CF ₃ 0 HHHO 3-CF ₃ 4-C (CH ₃ ) ₃ 4-OCF ₃ 0 HHHO 3- CF ₃ 4-CH ₂ CH = CH ₂ 4-Cl 0 HHHO 3-CF ₃ 4-Q1 4-CF ₃ 0 HHHO 3-CF ₃ 4-Q2 4-OCF ₃ 0 HHHO 3-CF ₃ 4-Q3 4- Cl 0 HHHO 3-CF ₃ 4-Q4 4-CF ₃₀ HHHO 3-CF ₃ 4-CHF ₂ 4-OCF ₃₀ HHHO 3-CF ₃ 4-CH ₂ Br 4-Cl 0 HHHO 3-CF ₃ 4- CH ₂ Cl 4-CF ₃ ──────────────────────────────── ──

[0060]

[Table 26] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 HHHO 3-CF ₃ 2-CF ₃ 4-Cl 0 HHHO 3-CF ₃ 3-CF ₃ 4-CF ₃ 0 HHHO 3-CF ₃ 4-CF ₃ 4-OCF ₃ 0 HHHO 3-CF ₃ 4-CH = C (Cl) CF ₃ 4-Cl 0 HHHO 3 -CF ₃ 4- (Q4-1-Cl) 4-CF ₃ 0 HHHO 3-CF ₃ 4-CH ₂ CN 4-OCF ₃ 0 HHHO 3-CF ₃ 4-CH ₂ OH 4-Cl 0 HHHO 3-CF ₃ 4-CH ₂ CO ₂ H 4-CF ₃ 0 HHHO 3-CF ₃ 4-OCH ₃ 4-OCF ₃ 0 HHHO 3-CF ₃ 4-OCH ₂ CH ₃ 4-Cl 0 HHHO 3-CF ₃ 4-OCH (CH ₃ ) ₂ 4-CF ₃ 0 HHHO 3-CF ₃ 4-OCH ₂ CH ₂ CH ₂ CH ₃ 4-OCF ₃ 0 HHHO 3-CF ₃ 4-OC (CH ₃ ) ₃ 4-Cl 0 HHHO 3- CF ₃ 4-O (Q4) 4-CF ₃ 0 HHHO 3-CF ₃ 4-OCHF ₂ 4-OCF ₃₀ HHHO 3-CF ₃ 4-OCF ₂ Br 4-Cl 0 HHHO 3-CF ₃ 2-OCF ₃ 4-CF ₃ HOH 3-CF ₃ 3-OCF ₃ 4-OCF ₃ 0 HHHO 3-CF ₃ 4-OCF ₃ 4-Cl 0 HHHO 3-CF ₃ 4-OCH ₂ CF ₃ 4-CF ₃ 0 HHHO 3 _{-CF 3 4-OCF 2 CF 3} 4-OCF 3 0 HHHO 3-CF 3 4-OCF 2 CHF 2 4-Cl 0 HHHO 3-CF 3 4-OCF 2 CHFCl 4-CF 3 ─── ───────────────────────────────

[0061]

[Table 27] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 HHHO 3-CF ₃ 4-OCF ₂ CHFBr 4- Cl 0 HHHO 3-CF ₃ 4-OCF ₂ CF ₂ CF ₃ 4-CF ₃ 0 HHHO 3-CF ₃ 4-OCH ₂ CH = CHCl 4-OCF ₃ 0 HHHO 3-CF ₃ 4-O (Q4-2, 2-Cl ₂ ) 4-Cl 0 HHHO 3-CF ₃ 4-SCH ₃ 4-CF ₃ 0 HHHO 3-CF ₃ 4-SCHF ₂ 4-OCF ₃ 0 HHHO 3-CF ₃ 4-SCF ₂ Br 4-Cl 0 HHHO 3-CF ₃ 4-SCF ₃ 4-CF ₃ 0 HHHO 3-CF ₃ 4-SCF ₂ CHF ₂ 4-OCF ₃ 0 HHHO 3-CF ₃ 4-SOCH ₃ 4-Cl 0 HHHO 3-CF ₃ 4 -SOCF ₃ 4-CF ₃ 0 HHHO 3-CF ₃ 4-SOCF ₂ CHF ₂ 4-OCF ₃ 0 HHHO 3-CF ₃ 4-SO ₂ CH ₃ 4-Cl 0 HHHO 3-CF ₃ 4-SO ₂ CF ₃ 4-CF ₃₀ HHHO 3-CF ₃ 4-SO ₂ CHF ₂ 4-OCF ₃₀ HHHO 3-CF ₃ 4-SO ₂ CF ₂ Br 4-Cl 0 HHHO 3-CF ₃ 4-CH ₂ OCH ₃ 4- CF ₃ 0 HHHO 3-CF ₃ 4-OCF ₂ CHFOCF ₃ 4-OCF ₃ 0 HHHO 3-CF ₃ 4-CH ₂ SCH ₃ 4-Cl 0 HHHO 3-CF ₃ 4-CH ₂ COCH ₃ 4-CF ₃ 0 HHHO 3-CF ₃ 4-CH ₂ CO ₂ CH ₃ 4-OCF ₃ 0 HHHO 3-CF ₃ 4-OCO ₂ CH ₃ 4-Cl 0 HH HO 3-CF ₃ 4-OCOCH ₃ 4-CF ₃ ────────────────────────────────────

[0062]

[Table 28] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 HHHO 3-CF ₃ 4-COCH ₃ 4-Cl 0 HHHO 3-CF ₃ 4-COCF ₃ 4-CF ₃ 0 HHHO 3-CF ₃ 4-CO ₂ CH ₂ CH ₃ 4-OCF ₃ 0 HHHO 3-CF ₃ 4-CO ₂ C (CH ₃ ) ₃ 4- Cl 0 HHHO 3-CF ₃ 4-CO ₂ CH ₂ CF ₃ 4-CF ₃ 0 HHHO 3-CF ₃ 4-OCH ₂ CO ₂ CH ₃ 4-OCF ₃ 0 HHHO 3-CF ₃ 4-NO ₂ 4-Cl 0 HHHO 3-CF ₃ 4-OH 4-CF ₃ 0 HHHO 3-CF ₃ 4-CO ₂ H 4-OCF ₃ 0 HHHO 3-CF ₃ 4-SCN 4-Cl 0 HHHO 3-CF ₃ 4-OSO ₂ CH ₃ 4-CF ₃ 0 HHHO 3-CF ₃ 4-OSO ₂ CF ₃ 4-OCF ₃ 0 HHHO 3-CF ₃ 4-CSCH ₃ 4-Cl 0 HHHO 3-CF ₃ 4-NH ₂ 4-CF ₃ 0 HHHO 3-CF ₃ 4-N (CH ₃ ) ₂ 4-OCF ₃ 0 HHHO 3-CF ₃ 4-N (CH ₃ ) CH ₂ CH = CH ₂ 4-Cl 0 HHHO 3-CF ₃ 4-CON (CH _{3) 2 4-CF 3 0} HHHO 3-CF 3 4-OCON (CH 3) 2 4-OCF 3 0 HHHO 3-CF 3 4-NHCOCH 3 4-Cl 0 HHHO 3-CF 3 4-SO 2 N ( CH ₃ ) ₂ 4-CF ₃ 0 HHHO 3-CF ₃ 4-Si (CH ₃ ) ₃ 4-OCF ₃ 0 HHHO 3-CF ₃ 4-C ₆ H ₅ 4-Cl 0 HHHO 3-CF ₃ 4 -(C ₆ H ₄ -4-Cl) 4-CF ₃ ────────────────────────────────────

[0063]

[Table 29] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 HHHO 3-CF ₃ 4-OC ₆ H ₅ 4 -Cl 0 HHHO 3-CF ₃ 4-O (C ₆ H ₄ -4-CF ₃ ) 4-CF ₃ 0 HHHO 3-CF ₃ 3-O (C ₆ H ₄ -4-CF ₃ ) 4-OCF ₃ 0 HHHO 3-CF ₃ 4-S (C ₆ H ₄ -4-CF ₃ ) 4-Cl 0 HHHO 3-CF ₃ 4-SO ₂ C ₆ H ₅ 4-CF ₃ 0 HHHO 3-CF ₃ 4-NH (C ₆ H ₄ -4-Cl) 4-OCF ₃ 0 HHHO 3-CF ₃ 4-CH ₂ C ₆ H ₅ 4-Cl 0 HHHO 3-CF ₃ 4-COC ₆ H ₅ 4-CF ₃ 0 HHHO 3 -CF ₃ 4-OCH ₂ (C ₆ H ₄ -4-CF ₃ ) 4-OCF ₃ 0 HHHO 3-CF ₃ 4-CH ₂ OC ₆ H ₅ 4-Cl 0 HHHO 3-CF ₃ 4-NHCH ₂ C ₆ H ₅ 4-CF ₃₀ HHHO 3-CF ₃ 4-CH ₂ CH ₂ C ₆ H ₅ 4-OCF ₃₀ HHHO 3-CF ₃ 4-N = NC ₆ H ₅ 4-Cl 0 HHHO 3-CF ₃ 4-CH = CHC ₆ H ₅ 4-CF ₃ 0 HHHO 3-CF ₃ 2-CH = CH-CH = CH-3 4-OCF ₃ 0 HHHO 3-CF ₃ 3-CH = CH-CH = CH-4 4-Cl 0 HHHO 3-CF ₃ 3-OCH ₂ O-4 4-CF ₃ 0 HHHO 3-CF ₃ 3-OCF ₂ O-4 4-OCF ₃ 0 HHHO 3-CF ₃ 3-OCH ₂ CH ₂ O -4 4-Cl 0 HHHO 3-CF ₃ 3-OCF ₂ CF ₂ O-4 4-C F ₃ 0 HHHO 3-CF ₃ 3-OCF ₂ CF ₂ -4 4-OCF ₃ 0 HHHO 3-CF ₃ 3-CF ₂ CF ₂ O-4 4-Cl 0 HHHO 3-CF ₃ 4-NHSO ₂ CH ₃ 4-CF ₃ ───────────────────────────────────

[0064]

[Table 30] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 HHHO 3-CF ₃ 2,3-F ₂ 4 -Cl 0 HHHO 3-CF ₃ 2,4-F ₂ 4-CF ₃ 0 HHHO 3-CF ₃ 2,5-F ₂ 4-OCF ₃ 0 HHHO 3-CF ₃ 2,6-F ₂ 4-Cl 0 HHHO 3-CF ₃ 3,4-F ₂ 4-CF ₃ 0 HHHO 3-CF ₃ 3,5-F ₂ 4-OCF ₃ 0 HHHO 3-CF ₃ 2,4-Cl ₂ 4-Cl 0 HHHO 3- CF ₃ 3,4-Cl ₂ 4-CF ₃ 0 HHHO 3-CF ₃ 3,4-Br ₂ 4-OCF ₃ 0 HHHO 3-CF ₃ 2,4-I ₂ 4-Cl 0 HHHO 3-CF ₃ 2 , 4- (CH ₃ ) ₂ 4-CF ₃ 0 HHHO 3-CF ₃ 3,4- (OCH ₃ ) ₂ 4-OCF ₃ 0 HHHO 3-CF ₃ 2-F-4-Cl 4-Cl 0 HHHO 3 -CF ₃ 2-F-4-Br 4-CF ₃ 0 HHHO 3-CF ₃ 2-F-4-CF ₃ 4-OCF ₃ 0 HHHO 3-CF ₃ 2-F-4-OCHF ₂ 4-Cl 0 HHHO 3-CF ₃ 2-F-4-OSO ₂ CF ₃ 4-CF ₃ 0 HHHO 3-CF ₃ 2-F-4-O (C ₆ H ₄ -4-Cl) 4-OCF ₃ 0 HHHO 3- CF ₃ 2-F-4-O (Q5-5-CF ₃ ) 4-Cl 0 HHHO 3-CF ₃ 3-Cl-4-CF ₃ 4-CF ₃ 0 HHHO 3-CF ₃ 3-F-4- _{OCF 3 4-OCF 3 0 HHHO} 3-CF 3 3,4- (CF 3) 2 4-Cl 0 HHHO 3-CF 3 3,4- (OCF 3) 2 4-CF 3 ─ ────────────────────────────────

[0065]

[Table 31] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 HHHO 3-CF ₃ 3-CN 4-Cl 0 HHHO 3-CF ₃ 2-Cl-4-CN 4-CF ₃ 0 HHHO 3-CF ₃ 3-Cl-4-CN 4-OCF ₃ 0 HHHO 3-CF ₃ 2-CH ₃ -4-CN 4-Cl 0 HHHO 3-CF ₃ 3-CH ₃ -4-CN 4-CF ₃ 0 HHHO 3-CF ₃ 3,4- (CN) ₂ 4-OCF ₃ 0 HHHO 3-CF ₃ 2,5-F ₂ -4 -Cl 4-Cl 0 HHHO 3-CF ₃ 3,5-F ₂ -4-CF ₃ 4-CF ₃ 0 HHHO 3-CF ₃ 2,3,4-F ₃ 4-OCF ₃ 0 HHHO 3-CF ₃ 2,4,5-F ₃ 4-Cl 0 HHHO 3-CF ₃ 3,4,5-F ₃ 4-CF ₃ 0 HHHO 3-CF ₃ 2,3,4-Cl ₃ 4-OCF ₃ 0 HHHO 3 -CF ₃ 2,4,5-Cl ₃ 4-Cl 0 HHHO 3-CF ₃ 2,4,6-Cl ₃ 4-CF ₃ 0 HHHO 3-CF ₃ 2-F-4,5-Cl ₂ 4- OCF ₃ 0 HHHO 3-CF ₃ 3-Cl-4-F 4-Cl 0 HHHO 3-CF ₃ 2-F-4-OCHF ₂ -5-Cl 4-CF ₃ 0 HHHO 3-CF ₃ 2,3, 4,5-F ₄ 4-OCF ₃ 0 HHHO 3-CF ₃ 2,3,5,6-F ₄ 4-Cl 0 HHHO 3-CF ₃ 2,4-F ₂ -3,5-Cl ₂ 4- CF ₃ 0 HHHO 3-CF ₃ 2,3,4,5,6-F ₅ 4-OCF ₃₀ HHHO 3-CF ₃ 2,3,5,6-F ₄ -4-CN 4-Cl 0 HHHO 3 -CF ₃ 4-NHCONH CH ₃ 4-CF ₃ ────────────────────────────────────

[0066]

[Table 32] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 HHHO 3-F 3-F 4-Cl 0 HHHO 3-F 3-Cl 4-CF ₃₀ HHHO 3-F 3-Br 4-OCF ₃₀ HHHO 3-F 4-CN 4-Cl 0 HHHO 3-F 4-NO ₂ 4-CF ₃₀ HHHO 3- F 4-CH ₃ 4-OCF ₃ 0 HHHO 3-F 4-CF ₃ 4-Cl 0 HHHO 3-F 4-OCH ₂ CH ₃ 4-CF ₃ 0 HHHO 3-F 4-OCHF ₂ 4-OCF ₃ 0 HHHO 3-F 4-OCH ₂ CF ₃ 4-Cl 0 HHHO 3-F 4-OCF ₂ Br 4-CF ₃ 0 HHHO 3-F 4-OCF ₂ CHF ₂ 4-OCF ₃ 0 HHHO 3-F 4-OSO ₂ CF ₃ 4-Cl 0 HHHO 3-F 4-SCHF ₂ 4-CF ₃ 0 HHHO 3-F 4-SCF ₃ 4-OCF ₃ 0 HHHO 3-F 4-SCH ₃ 4-Cl 0 HHHO 3-F 4 -SOCH ₃ 4-CF ₃ 0 HHHO 3-F 4-SO ₂ CH ₃ 4-OCF ₃ 0 HHHO 3-F 4-OSO ₂ CH ₃ 4-Cl 0 HHHO 3-F 4-NHCOCH ₃ 4-CF ₃ 0 HHHO 3-F 4-NHSO ₂ CH ₃ 4-OCF ₃ 0 HHHO 3-F 2,4-Cl ₂ 4-Cl 0 HHHO 3-F 3-OCF ₂ O-4 4-CF ₃ ─────── ─────────────────────────────

[0067]

[Table 33] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 HHHO 3-OCHF ₂ 3-F 4-Cl 0 HHHO 3-OCHF ₂ 4-Cl 4-CF ₃₀ HHHO 3-OCHF ₂ 4-Br 4-OCF ₃₀ HHHO 3-OCHF ₂ 4-CN 4-Cl 0 HHHO 3-OCHF ₂ 4-NO ₂ 4-CF ₃ 0 HHHO 3-OCHF ₂ 4-CH ₃ 4-OCF ₃ 0 HHHO 3-OCHF ₂ 4-CF ₃ 4-Cl 0 HHHO 3-OCHF ₂ 4-OCH ₂ CH ₃ 4-CF ₃ 0 HHHO 3-OCHF ₂ 4-OCHF ₂ 4-OCF ₃₀ HHHO 3-OCHF ₂ 4-OCH ₂ CF ₃ 4-Cl 0 HHHO 3-OCHF ₂ 4-OCF ₂ Br 4-CF ₃ 0 HHHO 3-OCHF ₂ 4-OCF ₂ CHF ₂ 4-OCF ₃ 0 HHHO 3-OCHF ₂ 4-OSO ₂ CF ₃ 4-Cl 0 HHHO 3-OCHF ₂ 4-SCHF ₂ 4-CF ₃ 0 HHHO 3-OCHF ₂ 4-SCF ₃ 4-OCF ₃ 0 HHHO 3 -OCHF ₂ 4-SCH ₃ 4-Cl 0 HHHO 3-OCHF ₂ 4-SOCH ₃ 4-CF ₃ 0 HHHO 3-OCHF ₂ 4-SO ₂ CH ₃ 4-OCF ₃ 0 HHHO 3-OCHF ₂ 4-OSO _{2 CH 3 4-Cl 0 HHHO 3} -OCHF 2 4-NHCOCH 3 4-CF 3 0 HHHO 3-OCHF 2 4-NHSO 2 CH 3 4-OCF 3 0 HHHO 3-OCHF 2 2,4-Cl 2 4-Cl _{0 HHHO 3-OCHF 2 3-} OCF 2 O-4 4-CF 3 ── ────────────────────────────────

[0068]

[Table 34] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 HHHO 4-OCHF ₂ 3-F 4-Cl 0 HHHO 4-OCHF ₂ 4-Cl 4-CF ₃₀ HHHO 4-OCHF ₂ 4-Br 4-OCF ₃₀ HHHO 4-OCHF ₂ 4-CN 4-Cl 0 HHHO 4-OCHF ₂ 4-NO ₂ 4-CF ₃ 0 HHHO 4-OCHF ₂ 4-CH ₃ 4-OCF ₃ 0 HHHO 4-OCHF ₂ 4-CF ₃ 4-Cl 0 HHHO 4-OCHF ₂ 4-OCH ₂ CH ₃ 4-CF ₃ 0 HHHO 4-OCHF ₂ 4-OCHF ₂ 4-OCF ₃₀ HHHO 4-OCHF ₂ 4-OCH ₂ CF ₃ 4-Cl 0 HHHO 4-OCHF ₂ 4-OCF ₂ Br 4-CF ₃ 0 HHHO 4-OCHF ₂ 4-OCF ₂ CHF ₂ 4-OCF ₃ 0 HHHO 4-OCHF ₂ 4-OSO ₂ CF ₃ 4-Cl 0 HHHO 4-OCHF ₂ 4-SCHF ₂ 4-CF ₃ 0 HHHO 4-OCHF ₂ 4-SCF ₃ 4-OCF ₃ 0 HHHO 4 -OCHF ₂ 4-SCH ₃ 4-Cl 0 HHHO 4-OCHF ₂ 4-SOCH ₃ 4-CF ₃ 0 HHHO 4-OCHF ₂ 4-SO ₂ CH ₃ 4-OCF ₃ 0 HHHO 4-OCHF ₂ 4-OSO ₂ CH ₃ 4-Cl 0 HHHO 4-OCHF ₂ 4-NHCOCH ₃ 4-CF ₃ 0 HHHO 4-OCHF ₂ 4-NHSO ₂ CH ₃ 4-OCF ₃ 0 HHHO 4-OCHF ₂ 2,4-Cl ₂ 4-Cl _{0 HHHO 4-OCHF 2 3-} OCF 2 O-4 4-CF 3 ── ────────────────────────────────

[0069]

[Table 35] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 HHHO 3-Cl H 4-Cl 0 HHHO 3- Cl 4-Cl 4-CF ₃₀ HHHO 3-Cl 4-Br 4-OCF ₃₀ HHHO 3-Cl 4-CN 4-Cl 0 HHHO 3-Cl 4-NO ₂ 4-CF ₃₀ HHHO 3-Cl 4 -CH ₃ 4-OCF ₃ 0 HHHO 3-Cl 4-CF ₃ 4-Cl 0 HHHO 3-Cl 4-OCH ₂ CH ₃ 4-CF ₃ 0 HHHO 3-Cl 4-OCHF ₂ 4-OCF ₃ 0 HHHO 3 -Cl 4-OCH ₂ CF ₃ 4-Cl 0 HHHO 3-Cl 4-OCF ₂ Br 4-CF ₃ 0 HHHO 3-Cl 4-OCF ₂ CHF ₂ 4-OCF ₃ 0 HHHO 3-Cl 4-OSO ₂ CF ₃ 4-Cl 0 HHHO 3-Cl 4-SCHF ₂ 4-CF ₃ 0 HHHO 3-Cl 4-SCF ₃ 4-OCF ₃ 0 HHHO 3-Cl 4-SCH ₃ 4-Cl 0 HHHO 3-Cl 4-SOCH ₃ 4-CF ₃₀ HHHO 3-Cl 4-SO ₂ CH ₃ 4-OCF ₃ 0 HHHO 3-Cl 4-OSO ₂ CH ₃ 4-Cl 0 HHHO 3-Cl 4-NHCOCH ₃ 4-CF ₃ 0 HHHO 3 -Cl 4-NHSO ₂ CH ₃ 4-OCF ₃ 0 HHHO 3-Cl 2,4-Cl ₂ 4-Cl 0 HHHO 3-Cl 3-OCF ₂ O-4 4-CF ₃ ───────── ───────────────────────── ─

[0070]

[Table 36] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 HHHO 3-Br H 4-Cl 0 HHHO 3- Br 4-Cl 4-CF ₃ 0 HHHO 3-Br 4-Br 4-OCF ₃ 0 HHHO 3-Br 4-CN 4-Cl 0 HHHO 3-Br 4-NO ₂ 4-CF ₃ 0 HHHO 3-Br 4 -CH ₃ 4-OCF ₃ 0 HHHO 3-Br 4-CF ₃ 4-Cl 0 HHHO 3-Br 4-OCH ₂ CH ₃ 4-CF ₃ 0 HHHO 3-Br 4-OCHF ₂ 4-OCF ₃ 0 HHHO 3 -Br 4-OCH ₂ CF ₃ 4-Cl 0 HHHO 3-Br 4-OCF ₂ Br 4-CF ₃ 0 HHHO 3-Br 4-OCF ₂ CHF ₂ 4-OCF ₃ 0 HHHO 3-Br 4-OSO ₂ CF ₃ 4-Cl 0 HHHO 3-Br 4-SCHF ₂ 4-CF ₃ 0 HHHO 3-Br 4-SCF ₃ 4-OCF ₃ 0 HHHO 3-Br 4-SCH ₃ 4-Cl 0 HHHO 3-Br 4-SOCH ₃ 4-CF ₃ 0 HHHO 3-Br 4-SO ₂ CH ₃ 4-OCF ₃ 0 HHHO 3-Br 4-OSO ₂ CH ₃ 4-Cl 0 HHHO 3-Br 4-NHCOCH ₃ 4-CF ₃ 0 HHHO 3 -Br 4-NHSO ₂ CH ₃ 4-OCF ₃ 0 HHHO 3-Br 2,4-Cl ₂ 4-Cl 0 HHHO 3-Br 3-OCF ₂ O-4 4-CF ₃ ───────── ───────────────────────── ─

[0071]

[Table 37] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 HHHO 3,4-F ₂ H 4-Cl 0 HHHO 3,4-F ₂ 4-Cl 4-CF ₃ 0 HHHO 3,4-F ₂ 4-Br 4-OCF ₃ 0 HHHO 3,4-F ₂ 4-CN 4-Cl 0 HHHO 3,4-F ₂ 4-NO ₂ 4-CF ₃₀ HHHO 3,4-F ₂ 4-CH ₃ 4-OCF ₃₀ HHHO 3,4-F ₂ 4-CF ₃ 4-Cl 0 HHHO 3,4-F ₂ 4- OCH ₂ CH ₃ 4-CF ₃ 0 HHHO 3,4-F ₂ 4-OCHF ₂ 4-OCF ₃ 0 HHHO 3,4-F ₂ 4-OCH ₂ CF ₃ 4-Cl 0 HHHO 3,4-F ₂ 4 -OCF ₂ Br 4-CF ₃₀ HHHO 3,4-F ₂ 4-OCF ₂ CHF ₂ 4-OCF ₃ 0 HHHO 3,4-F ₂ 4-OSO ₂ CF ₃ 4-Cl 0 HHHO 3,4-F ₂ 4-SCHF ₂ 4-CF ₃ 0 HHHO 3,4-F ₂ 4-SCF ₃ 4-OCF ₃ 0 HHHO 3,4-F ₂ 4-SCH ₃ 4-Cl 0 HHHO 3,4-F ₂ 4- SOCH ₃ 4-CF ₃ 0 HHHO 3,4-F ₂ 4-SO ₂ CH ₃ 4-OCF ₃ 0 HHHO 3,4-F ₂ 4-OSO ₂ CH ₃ 4-Cl 0 HHHO 3,4-F ₂ 4 -NHCOCH ₃ 4-CF ₃ 0 HHHO 3,4-F ₂ 4-NHSO ₂ CH ₃ 4-OCF ₃ 0 HHHO 3,4-F ₂ 2,4-Cl ₂ 4-Cl 0 HHHO 3,4-F _{2 3-OCF 2 O-4 4} -CF 3 ────────── ────────────────────────

[0072]

[Table 38] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 HHHO 4-Cl 4-F 4-Cl 0 HHHO 4-Cl 4-Cl 4-CF ₃₀ HHHO 4-Cl 4-Br 4-OCF ₃ 0 HHHO 4-Cl 4-CN 4-Cl 0 HHHO 4-Cl 4-NO ₂ 4-CF ₃₀ HHHO 4- Cl 4-CH ₃ 4-OCF ₃ 0 HHHO 4-Cl 4-CF ₃ 4-Cl 0 HHHO 4-Cl 4-OCH ₂ CH ₃ 4-CF ₃ 0 HHHO 4-Cl 4-OCHF ₂ 4-OCF ₃ 0 HHHO 4-Cl 4-OCH ₂ CF ₃ 4-Cl 0 HHHO 4-Cl 4-OCF ₂ Br 4-CF ₃ 0 HHHO 4-Cl 4-OCF ₂ CHF ₂ 4-OCF ₃ 0 HHHO 4-Cl 4-OSO ₂ CF ₃ 4-Cl 0 HHHO 4-Cl 4-SCHF ₂ 4-CF ₃ 0 HHHO 4-Cl 4-SCF ₃ 4-OCF ₃ 0 HHHO 4-Cl 4-SCH ₃ 4-Cl 0 HHHO 4-Cl 4 -SOCH ₃ 4-CF ₃ 0 HHHO 4-Cl 4-SO ₂ CH ₃ 4-OCF ₃ 0 HHHO 4-Cl 4-OSO ₂ CH ₃ 4-Cl 0 HHHO 4-Cl 4-NHCOCH ₃ 4-CF ₃ 0 HHHO 4-Cl 4-NHSO ₂ CH ₃ 4-OCF ₃ 0 HHHO 4-Cl 2,4-Cl ₂ 4-Cl 0 HHHO 4-Cl 3-OCF ₂ O-4 4-CF ₃ ─────── ──────────────────────────── ──

[0073]

[Table 39] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 HHHO 2-F 4-F 4-Cl 0 HHHO 2-Cl 4-F 4-CF ₃ 0 HHHO 4-Cl 4-F 4-OCF ₃ 0 HHHO 4-Br 4-F 4-Cl 0 HHHO 3-I 4-F 4-CF ₃ 0 HHHO 4-I 4-F 4-OCF ₃ 0 HHHO 3-CH ₃ 4-F 4-Cl 0 HHHO 4-CH ₃ 4-F 4-CF ₃ 0 HHHO 4-CH ₂ CH ₃ 4-F 4-OCF ₃ 0 HHHO 3 -CH (CH ₃ ) ₂ 4-F 4-Cl 0 HHHO 4-CH ₂ CH ₂ CH ₂ CH ₃ 4-F 4-CF ₃ 0 HHHO 4-C (CH ₃ ) ₃ 4-F 4-OCF ₃ 0 HHHO 3-CH ₂ CH = CH ₂ 4-F 4-Cl 0 HHHO 4-Q1 4-F 4-CF ₃ 0 HHHO 4-Q2 4-F 4-OCF ₃ 0 HHHO 4-Q3 4-F 4-Cl 0 HHHO 4-Q4 4-F 4-CF ₃ 0 HHHO 3-CHF ₂ 4-F 4-OCF ₃ 0 HHHO 4-CHF ₂ 4-F 4-Cl 0 HHHO 3-CH ₂ Br 4-F 4-CF ₃ 0 HHHO 3-CH ₂ Cl 4-F 4-OCF ₃₀ HHHO 2-CF ₃ 4-F 4-Cl 0 HHHO 4-CF ₃ 4-F 4-CF ₃ ─────────── ─────────────────────────

[0074]

[Table 40] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 HHHO 4-CH ₂ CN 4-F 4-Cl 0 HHHO 4-CH ₂ OH 4-F 4-CF ₃ 0 HHHO 4-CH ₂ CO ₂ H 4-F 4-OCF ₃ 0 HHHO 3-OCH ₃ 4-F 4-Cl 0 HHHO 4-OCH ₃ 4- F 4-CF ₃ 0 HHHO 3-OCH ₂ CH ₃ 4-F 4-OCF ₃ 0 HHHO 4-OCH (CH ₃ ) ₂ 4-F 4-Cl 0 HHHO 4-OC (CH ₃ ) ₃ 4-F 4 -CF ₃ 0 HHHO 2-OCHF ₂ 4-F 4-OCF ₃ 0 HHHO 3-OCF ₂ Br 4-F 4-Cl 0 HHHO 4-OCF ₂ Br 4-F 4-CF ₃ 0 HHHO 4-OCF ₃ 4 -F 4-OCF ₃ 0 HHHO 3-OCH ₂ CF ₃ 4-F 4-Cl 0 HHHO 4-OCH ₂ CF ₃ 4-F 4-CF ₃ 0 HHHO 3-OCF ₂ CF ₃ 4-F 4-OCF ₃ 0 HHHO 4-OCF ₂ CF ₃ 4-F 4-Cl 0 HHHO 2-OCF ₂ CHF ₂ 4-F 4-CF ₃ 0 HHHO 4-OCF ₂ CHF ₂ 4-F 4-OCF ₃ 0 HHHO 3-OCF ₂ CHFCl 4-F 4-Cl 0 HHHO 4-OCF ₂ CHFBr 4-F 4-CF ₃ 0 HHHO 3-OCF ₂ CF ₂ CF ₃ 4-F 4-OCF ₃ 0 HHHO 3-OCH ₂ CH = CHCl 4-F 4-Cl 0 HHHO 3-O (Q1-2,2-Cl 2) 4-F 4-CF 3 ──────────────── ──────────────────

[0075]

[Table 41] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 HHHO 3-SCH ₃ 4-F 4-Cl 0 HHHO 4-SCH ₃ 4-F 4-CF ₃ 0 HHHO 3-SCHF ₂ 4-F 4-OCF ₃ 0 HHHO 4-SCHF ₂ 4-F 4-Cl 0 HHHO 3-SCF ₃ 4-F 4-CF ₃ 0 HHHO 4-SCF ₃ 4-F 4-OCF ₃ 0 HHHO 3-SOCH ₃ 4-F 4-Cl 0 HHHO 4-SOCH ₃ 4-F 4-CF ₃ 0 HHHO 3-SO ₂ CH ₃ 4-F 4 -OCF ₃ 0 HHHO 4-SO ₂ CH ₃ 4-F 4-Cl 0 HHHO 3-SO ₂ CHF ₂ 4-F 4-CF ₃ 0 HHHO 4-CH ₂ OCH ₃ 4-F 4-OCF ₃ 0 HHHO 3 -OCF ₂ CHFOCF ₃ 4-F 4-Cl 0 HHHO 4-OCF ₂ CHFOCF ₃ 4-F 4-CF ₃ 0 HHHO 4-CH ₂ COCH ₃ 4-F 4-OCF ₃ 0 HHHO 4-CH ₂ CO ₂ CH ₃ 4-F 4-Cl 0 HHHO 4-OCO ₂ CH ₃ 4-F 4-CF ₃ 0 HHHO 3-OCOCH ₃ 4-F 4-OCF ₃ 0 HHHO 4-COCH ₃ 4-F 4-Cl 0 HHHO 4 -COCF ₃ 4-F 4-CF ₃ 0 HHHO 4-CO ₂ CH ₂ CH ₃ 4-F 4-OCF ₃ 0 HHHO 4-CO ₂ C (CH ₃ ) ₃ 4-F 4-Cl 0 HHHO 3-CO _{2 CH 2 CF 3 4-F} 4-CF 3 ───────────────────── ─────────────

[0076]

[Table 42] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 HHHO 3-NO ₂ 4-F 4-Cl 0 HHHO 4-NO ₂ 4-F 4-CF ₃ 0 HHHO 3-CN 4-F 4-OCF ₃ 0 HHHO 4-CN 4-F 4-Cl 0 HHHO 3-OH 4-F 4-CF ₃ 0 HHHO 4 -OH 4-F 4-OCF ₃ 0 HHHO 4-SCN 4-F 4-Cl 0 HHHO 3-OSO ₂ CH ₃ 4-F 4-CF ₃ 0 HHHO 4-OSO ₂ CH ₃ 4-F 4-OCF ₃ 0 HHHO 3-OSO ₂ CF ₃ 4-F 4-Cl 0 HHHO 4-OSO ₂ CF ₃ 4-F 4-CF ₃ 0 HHHO 4-CSCH ₃ 4-F 4-OCF ₃ 0 HHHO 4-NH ₂ 4- F 4-Cl 0 HHHO 4-N (CH ₃ ) ₂ 4-F 4-CF ₃ 0 HHHO 4-CON (CH ₃ ) ₂ 4-F 4-OCF ₃ 0 HHHO 3-OCON (CH ₃ ) ₂ 4- F 4-Cl 0 HHHO 4-NHCOCH ₃ 4-F 4-CF ₃ 0 HHHO 4-SO ₂ N (CH ₃ ) ₂ 4-F 4-OCF ₃ 0 HHHO 4-Si (CH ₃ ) ₃ 4-F 4 -Cl 0 HHHO 4-C ₆ H ₅ 4-F 4-CF ₃ 0 HHHO 3-OC ₆ H ₅ 4-F 4-OCF ₃ 0 HHHO 4-OC ₆ H ₅ 4-F 4-Cl 0 HHHO 3- SC ₆ H ₅ 4-F 4-CF ₃ ─────────────────────────────────── ─

[0077]

[Table 43] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 HHHO 3-SO ₂ C ₆ H ₅ 4-F 4-Cl 0 HHHO 3-NHC ₆ H ₅ 4-F 4-CF ₃ 0 HHHO 3-CH ₂ C ₆ H ₅ 4-F 4-OCF ₃₀ HHHO 3-COC ₆ H ₅ 4-F 4-Cl 0 HHHO 3-NHSO ₂ CH ₃ 4-F 4-CF ₃ 0 HHHO 2-CH = CH-CH = CH-3 4-F 4-OCF ₃ 0 HHHO 3-CH = CH-CH = CH-4 4-F 4-Cl 0 HHHO 3-OCH ₂ O-4 4-F 4-CF ₃ 0 HHHO 3-OCF ₂ O-4 4-F 4-OCF ₃ 0 HHHO 3-OCH ₂ CH ₂ O-4 4-F 4 -Cl 0 HHHO 3-OCF ₂ CF ₂ O-4 4-F 4-CF ₃ 0 HHHO 2,3-F ₂ 4-F 4-OCF ₃ 0 HHHO 2,4-F ₂ 4-F 4-Cl 0 HHHO 2,5-F ₂ 4-F 4-CF ₃ 0 HHHO 3,5-F ₂ 4-F 4-OCF ₃ 0 HHHO 3,4-Cl ₂ 4-F 4-Cl 0 HHHO 3,5-Cl ₂ 4-F 4-CF ₃₀ HHHO 3,4-Br ₂ 4-F 4-OCF ₃₀ HHHO 3,5-I ₂ 4-F 4-Cl 0 HHHO 2,4- (CH ₃ ) ₂ 4- F 4-CF ₃ 0 HHHO 3,4- (OCH ₃ ) ₂ 4-F 4-OCF ₃ 0 HHHO 3,4- (OCF ₃ ) ₂ 4-F 4-Cl 0 HHHO 3,5- (OCHF ₂ ) _{2 4-F 4-CF 3} ────────────────── ────────────────

[0078]

[Table 44] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 HHHO 3,4- (CF ₃ ) ₂ 4- F 4-Cl 0 HHHO 3,5- (CF ₃ ) ₂ 4-F 4-CF ₃ 0 HHHO 2-F-4-Cl 4-F 4-OCF ₃ 0 HHHO 3-F-5-Cl 4-F 4-Cl 0 HHHO 3-F-5-CF ₃ 4-F 4-CF ₃ 0 HHHO 3-F-5-OCHF ₂ 4-F 4-OCF ₃₀ HHHO 3-Cl-5-CF ₃ 4-F 4-Cl 0 HHHO 3-Cl-4-OCHF ₂ 4-F 4-CF ₃ 0 HHHO 3-Cl-4-CN 4-F 4-OCF ₃ 0 HHHO 3-Cl-4-F 4-F 4- Cl 0 HHHO 3-Cl-5-OSO ₂ CF ₃ 4-F 4-CF ₃ 0 HHHO 3-F-4-OSO ₂ CF ₃ 4-F 4-OCF ₃ 0 HHHO 2,3,4-F ₃ 4 -F 4-Cl 0 HHHO 3,4,5-F ₃ 4-F 4-CF ₃ 0 HHHO 2,4,5-Cl ₃ 4-F 4-OCF ₃ 0 HHHO 2,4,6-Cl ₃ 4 -F 4-Cl 0 HHHO 2-F-4,5-Cl ₂ 4-F 4-CF ₃ 0 HHHO 3,5-Cl ₂ -4-CF ₃ 4-F 4-OCF ₃ 0 HHHO 2,3, 4,5-F ₄ 4-F 4-Cl 0 HHHO 2,3,5,6-F ₄ 4-F 4-CF ₃ 0 HHHO 2,4-F ₂ -3,5-Cl ₂ 4-F 4 -OCF ₃ 0 HHHO 2,3,4,5,6-F ₅ 4-F 4-Cl 0 HHHO 2,3,5,6-F ₄ -4-CN 4-F 4-CF ₃ ──── ────────── ────────────────────

[0079]

[Table 45] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 HHHO 4-F 4-Cl 4-Cl 0 HHHO 3-Cl 4-Cl 4-CF ₃₀ HHHO 4-Cl 4-Cl 4-OCF ₃ 0 HHHO 3-Br 4-Cl 4-Cl 0 HHHO 3-CH ₃ 4-Cl 4-CF ₃₀ HHHO 4- CF ₃ 4-Cl 4-OCF ₃ 0 HHHO 3-OCH ₃ 4-Cl 4-Cl 0 HHHO 3-OCHF ₂ 4-Cl 4-CF ₃ 0 HHHO 4-OCHF ₂ 4-Cl 4-OCF ₃ 0 HHHO 3 -OCF ₂ Br 4-Cl 4-Cl 0 HHHO 3-OCF ₃ 4-Cl 4-CF ₃ 0 HHHO 3-OCH ₂ CF ₃ 4-Cl 4-OCF ₃ 0 HHHO 3-OCF ₂ CHF ₂ 4-Cl 4 -Cl 0 HHHO 3-SCHF ₂ 4-Cl 4-CF ₃ 0 HHHO 3-SCF ₃ 4-Cl 4-OCF ₃ 0 HHHO 3-NO ₂ 4-Cl 4-Cl 0 HHHO 3-CN 4-Cl 4- CF ₃ 0 HHHO 3-OSO ₂ CH ₃ 4-Cl 4-OCF ₃ 0 HHHO 3-OSO ₂ CF ₃ 4-Cl 4-Cl 0 HHHO 4-OSO ₂ CF ₃ 4-Cl 4-CF ₃ 0 HHHO 3, 4-F ₂ 4-Cl 4-OCF ₃ 0 HHHO 3,5-F ₂ 4-Cl 4-Cl 0 HHHO 3-Cl-4-F 4-Cl 4-CF ₃ ───────── ──────────────────────────

[0080]

[Table 46] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 HHHO 4-F 4-Br 4-Cl 0 HHHO 3-Cl 4-Br 4-CF ₃₀ HHHO 4-Cl 4-Br 4-OCF ₃ 0 HHHO 3-Br 4-Br 4-Cl 0 HHHO 3-CH ₃ 4-Br 4-CF ₃₀ HHHO 4- CF ₃ 4-Br 4-OCF ₃ 0 HHHO 3-OCH ₃ 4-Br 4-Cl 0 HHHO 3-OCHF ₂ 4-Br 4-CF ₃ 0 HHHO 4-OCHF ₂ 4-Br 4-OCF ₃ 0 HHHO 3 -OCF ₂ Br 4-Br 4-Cl 0 HHHO 3-OCF ₃ 4-Br 4-CF ₃ 0 HHHO 3-OCH ₂ CF ₃ 4-Br 4-OCF ₃ 0 HHHO 3-OCF ₂ CHF ₂ 4-Br 4 -Cl 0 HHHO 3-SCHF ₂ 4-Br 4-CF ₃ 0 HHHO 3-SCF ₃ 4-Br 4-OCF ₃ 0 HHHO 3-NO ₂ 4-Br 4-Cl 0 HHHO 3-CN 4-Br 4- CF ₃ 0 HHHO 3-OSO ₂ CH ₃ 4-Br 4-OCF ₃ 0 HHHO 3-OSO ₂ CF ₃ 4-Br 4-Cl 0 HHHO 4-OSO ₂ CF ₃ 4-Br 4-CF ₃ 0 HHHO 3, 4-F ₂ 4-Br 4-OCF ₃ 0 HHHO 3,5-F ₂ 4-Br 4-Cl 0 HHHO 3-Cl-4-F 4-Br 4-CF ₃ ───────── ──────────────────────────

[0081]

[Table 47] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 HHHO 4-F 4-CN 4-Cl 0 HHHO 2-Cl 4-CN 4-CF ₃₀ HHHO 4-Cl 4-CN 4-OCF ₃ 0 HHHO 3-Br 4-CN 4-Cl 0 HHHO 3-CH ₃ 4-CN 4-CF ₃₀ HHHO 4- CF ₃ 4-CN 4-OCF ₃ 0 HHHO 3-OCH ₃ 4-CN 4-Cl 0 HHHO 3-OCHF ₂ 4-CN 4-CF ₃ 0 HHHO 4-OCHF ₂ 4-CN 4-OCF ₃ 0 HHHO 3 -OCF ₂ Br 4-CN 4-Cl 0 HHHO 3-OCF ₃ 4-CN 4-CF ₃ 0 HHHO 3-OCF ₃ 4-CN 4-OCF ₃ 0 HHHO 3-OCH ₂ CF ₃ 4-CN 4-OCF ₃₀ HHHO 3-OCF ₂ CHF ₂ 4-CN 4-Cl 0 HHHO 3-SCHF ₂ 4-CN 4-CF ₃₀ HHHO 3-SCF ₃ 4-CN 4-OCF ₃₀ HHHO 3-NO ₂ 4-CN 4-Cl 0 HHHO 3-CN 4-CN 4-CF ₃ 0 HHHO 3-OSO ₂ CH ₃ 4-CN 4-OCF ₃ 0 HHHO 3-OSO ₂ CF ₃ 4-CN 4-Cl 0 HHHO 4-OSO ₂ CF ₃ 4-CN 4-CF ₃₀ HHHO 3,4-F ₂ 4-CN 4-OCF ₃₀ HHHO 3,5-F ₂ 4-CN 4-Cl ──────────── ───────────────────────

[0082]

[Table 48] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 HHHO 3-Cl-4-F 4-CN 4 -CF ₃ 0 HHHO 4-F 4-OHCF ₂ 4-Cl 0 HHHO 3-Cl 4-OHCF ₂ 4-CF ₃ 0 HHHO 4-Cl 4-OHCF ₂ 4-OCF ₃ 0 HHHO 3-Br 4-OHCF ₂ 4-Cl 0 HHHO 3-CH ₃ 4-OHCF ₂ 4-CF ₃ 0 HHHO 4-CF ₃ 4-OHCF ₂ 4-OCF ₃ 0 HHHO 3-OCH ₃ 4-OHCF ₂ 4-Cl 0 HHHO 3-OCHF ₂ 4-OHCF ₂ 4-CF ₃ 0 HHHO 4-OCHF ₂ 4-OHCF ₂ 4-OCF ₃ 0 HHHO 3-OCF ₂ Br 4-OHCF ₂ 4-Cl 0 HHHO 3-OCF ₃ 4-OHCF ₂ 4-CF ₃ 0 HHHO 3-OCH ₂ CF ₃ 4-OHCF ₂ 4-OCF ₃ 0 HHHO 3-OCF ₂ CHF ₂ 4-OHCF ₂ 4-Cl 0 HHHO 3-SCHF ₂ 4-OHCF ₂ 4-CF ₃ 0 HHHO 3-SCF ₃ 4-OHCF ₂ 4-OCF ₃ 0 HHHO 3-NO ₂ 4-OHCF ₂ 4-Cl 0 HHHO 3-CN 4-OHCF ₂ 4-CF ₃ 0 HHHO 3-OSO ₂ CH ₃ 4-OHCF ₂ 4-OCF ₃ 0 HHHO 3-OSO ₂ CF ₃ 4-OHCF ₂ 4-Cl 0 HHHO 4-OSO ₂ CF ₃ 4-OHCF ₂ 4-CF ₃ 0 HHHO 3,4-F ₂ 4-OHCF ₂ 4-OCF ₃ 0 HHHO _{3,5-F 2 4-OHCF 2} 4-Cl ────────── ────────────────────────

[0083]

[Table 49] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 HHHO 3-Cl-4-F 4-OHCF ₂ 4-CF ₃ 0 HHHO 4-F 4-OSO ₂ CF ₃ 4-Cl 0 HHHO 3-Cl 4-OSO ₂ CF ₃ 4-CF ₃ 0 HHHO 4-Cl 4-OSO ₂ CF ₃ 4-OCF ₃ 0 HHHO 3-Br 4-OSO ₂ CF ₃ 4-Cl 0 HHHO 3-CH ₃ 4-OSO ₂ CF ₃ 4-CF ₃ 0 HHHO 4-CF ₃ 4-OSO ₂ CF ₃ 4-OCF ₃ 0 HHHO 3-OCH ₃ 4-OSO ₂ CF ₃ 4-Cl 0 HHHO 3-OCHF ₂ 4-OSO ₂ CF ₃ 4-CF ₃ 0 HHHO 4-OCHF ₂ 4-OSO ₂ CF ₃ 4-OCF ₃ 0 HHHO 3-OCF ₂ Br 4- OSO ₂ CF ₃ 4-Cl 0 HHHO 3-OCF ₃ 4-OSO ₂ CF ₃ 4-CF ₃ 0 HHHO 3-OCH ₂ CF ₃ 4-OSO ₂ CF ₃ 4-OCF ₃ 0 HHHO 3-OCF ₂ CHF ₂ 4 -OSO ₂ CF ₃ 4-Cl 0 HHHO 3-SCHF ₂ 4-OSO ₂ CF ₃ 4-CF ₃ 0 HHHO 3-SCF ₃ 4-OSO ₂ CF ₃ 4-OCF ₃ 0 HHHO 3-NO ₂ 4-OSO ₂ CF ₃ 4-Cl 0 HHHO 3-CN 4-OSO ₂ CF ₃ 4-CF ₃ 0 HHHO 3-OSO ₂ CH ₃ 4-OSO ₂ CF ₃ 4-OCF ₃ 0 HHHO 3-OSO ₂ CF ₃ 4-OSO ₂ CF ₃ 4-Cl 0 HHHO 4-OSO ₂ CF ₃ 4-OSO ₂ CF ₃ 4-CF ₃ 0 HHHO 3 , 4-F ₂ 4-OSO ₂ CF ₃ 4-OCF ₃ 0 HHHO 3,5-F ₂ 4-OSO ₂ CF ₃ 4-Cl ─────────────────── ─────────────────

[0084]

[Table 50] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 HHHO 3-Cl-4-F 4-OSO ₂ CF ₃ 4-CF ₃ 0 HHHO 4-F 4-OCF ₂ CHF ₂ 4-Cl 0 HHHO 3-Cl 4-OCF ₂ CHF ₂ 4-CF ₃ 0 HHHO 4-Cl 4-OCF ₂ CHF ₂ 4-OCF ₃ 0 HHHO 3-Br 4-OCF ₂ CHF ₂ 4-Cl 0 HHHO 3-CH ₃ 4-OCF ₂ CHF ₂ 4-CF ₃ 0 HHHO 4-CF ₃ 4-OCF ₂ CHF ₂ 4-OCF ₃ 0 HHHO 3- OCH ₃ 4-OCF ₂ CHF ₂ 4-Cl 0 HHHO 3-OCHF ₂ 4-OCF ₂ CHF ₂ 4-CF ₃ 0 HHHO 4-OCHF ₂ 4-OCF ₂ CHF ₂ 4-OCF ₃ 0 HHHO 3-OCF ₂ Br 4-OCF ₂ CHF ₂ 4-Cl 0 HHHO 3-OCF ₃ 4-OCF ₂ CHF ₂ 4-CF ₃ 0 HHHO 3-OCH ₂ CF ₃ 4-OCF ₂ CHF ₂ 4-OCF ₃ 0 HHHO 3-OCF ₂ CHF ₂ 4-OCF ₂ CHF ₂ 4-Cl 0 HHHO 3-SCHF ₂ 4-OCF ₂ CHF ₂ 4-CF ₃ 0 HHHO 3-SCF ₃ 4-OCF ₂ CHF ₂ 4-OCF ₃ 0 HHHO 3-NO ₂ 4- OCF ₂ CHF ₂ 4-Cl 0 HHHO 3-CN 4-OCF ₂ CHF ₂ 4-CF ₃ 0 HHHO 3-OSO ₂ CH ₃ 4-OCF ₂ CHF ₂ 4-OCF ₃ 0 HHHO 3-OSO ₂ CF ₃ 4- OCF ₂ CHF ₂ 4-Cl 0 HHHO 4-OSO ₂ CF ₃ 4-OCF ₂ CHF ₂ 4-CF ₃ 0 HHHO 3,4-F ₂ 4-OCF ₂ CHF ₂ 4-OCF ₃ 0 HHHO 3,5-F ₂ 4-OCF ₂ CHF ₂ 4-Cl ───────── ────────────────────────────

[0085]

[Table 51] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 HHHO 3-Cl-4-F 4-OCF ₂ CHF ₂ 4-CF ₃ 0 HHHO 4-F 2,4-F ₂ 4-Cl 0 HHHO 3-Cl 2,4-F ₂ 4-CF ₃ 0 HHHO 4-Cl 2,4-F ₂ 4-OCF ₃ 0 HHHO 3-Br 2,4-F ₂ 4-Cl 0 HHHO 3-CH ₃ 2,4-F ₂ 4-CF ₃ 0 HHHO 4-CF ₃ 2,4-F ₂ 4-OCF ₃ 0 HHHO 3- OCH _3, 2,4-F ₂ 4-Cl 0 HHHO 3-OCHF ₂ 2,4-F ₂ 4-CF ₃ 0 HHHO 4-OCHF ₂ 2,4-F ₂ 4-OCF ₃ 0 HHHO 3-OCF ₂ Br 2,4-F ₂ 4-Cl 0 HHHO 3-OCF ₃ 2,4-F ₂ 4-CF ₃ 0 HHHO 3-OCH ₂ CF ₃ 2,4-F ₂ 4-OCF ₃ 0 HHHO 3-OCF ₂ CHF ₂ 2,4-F ₂ 4-Cl 0 HHHO 3-SCHF ₂ 2,4-F ₂ 4-CF ₃ 0 HHHO 3-SCF ₃ 2,4-F ₂ 4-OCF ₃ 0 HHHO 3-NO ₂ 2, 4-F ₂ 4-Cl 0 HHHO 3-CN 2,4-F ₂ 4-CF ₃ 0 HHHO 3-OSO ₂ CH ₃ 2,4-F ₂ 4-OCF ₃ 0 HHHO 3-OSO ₂ CF ₃ 2, 4-F ₂ 4-Cl 0 HHHO 4-OSO ₂ CF ₃ 2,4-F ₂ 4-CF ₃ 0 HHHO 3,4-F ₂ 2,4-F ₂ 4-OCF ₃ 0 HHHO 3,5-F _{2 2,4-F 2 4-Cl} ────────────── ────────────────────

[0086]

[Table 52] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 HHHO 3-Cl-4-F 2,4- F ₂ 4-CF ₃ 0 HHHO 4-F 3,4-F ₂ 4-Cl 0 HHHO 3-Cl 3,4-F ₂ 4-CF ₃ 0 HHHO 4-Cl 3,4-F ₂ 4-OCF ₃ 0 HHHO 3-Br 3,4-F ₂ 4-Cl 0 HHHO 3-CH ₃ 3,4-F ₂ 4-CF ₃ 0 HHHO 4-CF ₃ 3,4-F ₂ 4-OCF ₃ 0 HHHO 3- OCH ₃ 3,4-F ₂ 4-Cl 0 HHHO 3-OCHF ₂ 3,4-F ₂ 4-CF ₃ 0 HHHO 4-OCHF ₂ 3,4-F ₂ 4-OCF ₃ 0 HHHO 3-OCF ₂ Br 3,4-F ₂ 4-Cl 0 HHHO 3-OCF ₃ 3,4-F ₂ 4-CF ₃ 0 HHHO 3-OCH ₂ CF ₃ 3,4-F ₂ 4-OCF ₃ 0 HHHO 3-OCF ₂ CHF ₂ 3,4-F ₂ 4-Cl 0 HHHO 3-SCHF ₂ 3,4-F ₂ 4-CF ₃ 0 HHHO 3-SCF ₃ 3,4-F ₂ 4-OCF ₃ 0 HHHO 3-NO ₂ 3, 4-F ₂ 4-Cl 0 HHHO 3-CN 3,4-F ₂ 4-CF ₃ 0 HHHO 3-OSO ₂ CH ₃ 3,4-F ₂ 4-OCF ₃ 0 HHHO 3-OSO ₂ CF ₃ 3, 4-F ₂ 4-Cl 0 HHHO 4-OSO ₂ CF ₃ 3,4-F ₂ 4-CF ₃ 0 HHHO 3,4-F ₂ 3,4-F ₂ 4-OCF ₃ 0 HHHO 3,5-F _{2 3,4-F 2 4-Cl} ──────────────── ──────────────────

[0087]

[Table 53] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 HHHO 3-Cl-4-F 3,4- F ₂ 4-CF ₃ 0 HHHS 3-F 4-F 4-Cl 0 HHHS 3-F 4-F 4-Br 0 HHHS 3-F 4-F 4-CF ₃ 0 HHHS 3-F 4-F 4- OCF ₃ 0 HHHS 3-F 4-F 4-OCHF ₂ 0 HHHS 3-F 4-F 4-OCF ₂ Br 0 HHHS 3-F 4-F 4-OCF ₂ CHF ₂₀ HHHS 3-F 4-F 4 -OSO ₂ CF ₃ 0 HHHSH 4-F 4-OCF ₃ 0 HHHS 4-F 4-F 4-Cl 0 HHHS 3-Cl 4-F 4-CF ₃ 0 HHHS 3-Br 4-F 4-OCF ₃ 0 HHHS 3-CF ₃ 4-F 4-Cl 0 HHHS 3-OCF ₃ 4-F 4-CF ₃ 0 HHHS 3-OCHF ₂ 4-F 4-OCF ₃ 0 HHHS 4-OCHF ₂ 4-F 4-Cl 0 HHHS 3-F 4-Cl 4-CF ₃ 0 HHHS 3-F 4-Br 4-OCF ₃ 0 HHHS 3-F 4-CF ₃ 4-Cl 0 HHHS 3-F 4-OSO ₂ CF ₃ 4-CF ₃ 0 HHHS 3-F 4-CN 4-OCF ₃ 0 HHHS 3-F 3,4-F ₂ 4-Cl ───────────────────────── ───────────

[0088]

[Table 54] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 HHHS 3-CF ₃ 4-CN 4-CF ₃ 0 HH CH ₃ O 3-F 4-F 4-Cl 0 HH CH ₃ O 3-F 4-F 4-Br 0 HH CH ₃ O 3-F 4-F 4-CF ₃ 0 HH CH ₃ O 3- F 4-F 4-OCF ₃ 0 HH CH ₃ O 3-F 4-F 4-OCHF ₂₀ HH CH ₃ O 3-F 4-F 4-OCF ₂ Br 0 HH CH ₃ O 3-F 4-F 4-OCF ₂ CHF ₂ 0 HH CH ₃ O 3-F 4-F 4-OSO ₂ CF ₃ 0 HH CH ₃ OH 4-F 4-OCF ₃ 0 HH CH ₃ S 4-F 4-F 4-Cl 0 HH CH ₃ O 3-Cl 4-F 4-CF ₃ 0 HH CH ₃ O 3-Br 4-F 4-OCF ₃ 0 HH CH ₃ O 3-CF ₃ 4-F 4-Cl 0 HH CH ₃ O 3 -OCF ₃ 4-F 4-CF ₃ 0 HH CH ₃ O 3-OCHF ₂ 4-F 4-OCF ₃ 0 HH CH ₃ O 4-OCHF ₂ 4-F 4-Cl 0 HH CH ₃ S 3-F 4 -Cl 4-CF ₃ 0 HH CH ₃ O 3-F 4-Br 4-OCF ₃ 0 HH CH ₃ O 3-F 4-CF ₃ 4-Cl 0 HH CH ₃ O 3-F 4-OSO ₂ CF ₃ 4-CF ₃₀ HH CH ₃ O 3-F 4-CN 4-OCF ₃₀ HH CH ₃ O 3-F 3,4-F ₂ 4-Cl ────────────── ───────────── ────────

[0089]

[Table 55] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 HH CH ₃ O 3-CF ₃ 4-CN 4 -CF ₃ 0 H CH ₃ HO 3-F 4-F 4-Cl 0 H CH ₃ HO 3-F 4-F 4-Br 0 H CH ₃ HO 3-F 4-F 4-CF ₃ 0 H CH ₃ HO 3-F 4-F 4-OCF ₃ 0 H CH ₃ HO 3-F 4-F 4-OCHF ₂ 0 H CH ₃ HO 3-F 4-F 4-OCF ₂ Br 0 H CH ₃ HO 3-F 4-F 4-OCF ₂ CHF ₂₀ H CH ₃ HO 3-F 4-F 4-OSO ₂ CF ₃ 0 H CH ₃ HOH 4-F 4-OCF ₃ 0 H CH ₃ HS 4-F 4-F 4 -Cl 0 H CH ₃ HO 3-Cl 4-F 4-CF ₃ 0 H CH ₃ HO 3-Br 4-F 4-OCF ₃ 0 H CH ₃ HO 3-CF ₃ 4-F 4-Cl 0 H CH ₃ HO 3-OCF ₃ 4-F 4-CF ₃ 0 H CH ₃ HO 3-OCHF ₂ 4-F 4-OCF ₃ 0 H CH ₃ HO 4-OCHF ₂ 4-F 4-Cl 0 H CH ₃ HS 3 -F 4-Cl 4-CF ₃ 0 H CH ₃ HO 3-F 4-Br 4-OCF ₃ 0 H CH ₃ HO 3-F 4-CF ₃ 4-Cl 0 H CH ₃ HO 3-F 4-OSO ₂ CF ₃ 4-CF ₃ 0 H CH ₃ HO 3-F 4-CN 4-OCF ₃ 0 H CH ₃ HO 3-F 3,4-F ₂ 4-Cl ─────────── ───────────── ──────────

[0090]

[Table 56] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 H CH ₃ HO 3-CF ₃ 4-CN 4 -CF ₃ 0 CH ₃ HHO 3-F 4-F 4-Cl 0 CH ₃ HHO 3-F 4-F 4-Br 0 CH ₃ HHO 3-F 4-F 4-CF ₃ 0 CH ₃ HHO 3-F 4-F 4-OCF ₃₀ CH ₃ HHO 3-F 4-F 4-OCHF ₂₀ CH ₃ HHO 3-F 4-F 4-OCF ₂ Br 0 CH ₃ HHO 3-F 4-F 4-OCF ₂ CHF ₂₀ CH ₃ HHO 3-F 4-F 4-OSO ₂ CF ₃ 0 CH ₃ HHOH 4-F 4-OCF ₃ 0 CH ₃ HHS 4-F 4-F 4-Cl 0 CH ₃ HHO 3-Cl 4 -F 4-CF ₃ 0 CH ₃ HHO 3-Br 4-F 4-OCF ₃ 0 CH ₃ HHO 3-CF ₃ 4-F 4-Cl 0 CH ₃ HHO 3-OCF ₃ 4-F 4-CF ₃ 0 CH ₃ HHO 3-OCHF ₂ 4-F 4-OCF ₃ 0 CH ₃ HHO 4-OCHF ₂ 4-F 4-Cl 0 CH ₃ HHS 3-F 4-Cl 4-CF ₃ 0 CH ₃ HHO 3-F 4 -Br 4-OCF ₃ 0 CH ₃ HHO 3-F 4-CF ₃ 4-Cl 0 CH ₃ HHO 3-F 4-OSO ₂ CF ₃ 4-CF ₃ 0 CH ₃ HHO 3-F 4-CN 4-OCF ₃ 0 CH ₃ HHO 3-F 3,4-F ₂ 4-Cl ───────────────────────────────── ───

[0091]

[Table 57] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 CH ₃ HHO 3-CF ₃ 4-CN 4- CF ₃ 0 HH CH ₂ CH ₃ O 3-F 4-F 4-Cl 0 HH CH ₂ CH ₂ CH ₃ O 3-F 4-F 4-Br 0 HH CH ₂ CH ₂ CH ₂ CH ₃ O 3-F 4-F 4-CF ₃ 0 HH CH (CH ₃ ) ₂ O 3-F 4-F 4-OCF ₃₀ HHC (CH ₃ ) ₃ O 3-F 4-F 4-OCHF ₂₀ HH CH ₂ CH = CH ₂ O 3-F 4-F 4-OCF ₂ Br 0 HH CH ₂ C ≡ CH O 3-F 4-F 4-OCF ₂ CHF ₂ 0 HH CH ₂ OCH ₃ O 3-F 4-F 4-OSO ₂ CF ₃ 0 HH CH ₂ OCH ₂ CH ₃ OH 4-F 4-OCF ₃ 0 HH CH ₂ CH ₂ OCH ₃ O 4-F 4-F 4-Cl 0 HH CHF ₂ O 3-Cl 4-F 4- CF ₃ 0 HH CBrF ₂ O 3-Br 4-F 4-OCF ₃ 0 HH CF ₃ O 3-CF ₃ 4-F 4-Cl 0 HH COCH ₃ O 3-OCF ₃ 4-F 4-CF ₃ 0 HH COCF ₃ O 3-OCHF ₂ 4-F 4-OCF ₃ 0 HH CO ₂ CH ₃ O 4-OCHF ₂ 4-F 4-Cl 0 HH CH ₂ C ₆ H ₅ O 3-F 4-Cl 4-CF ₃ 0 HH SC ₆ H ₅ O 3-F 4-Br 4-OCF ₃ 0 HH SCCl ₃ O 3-F 4-CF ₃ 4-Cl 0 HH SCO ₂ CH ₂ CH ₃ O 3-F 4-OSO ₂ CF ₃ 4-CF ₃ 0 HHS (C ₆ H ₄ -2-NO ₂ ) O 3-F 4-CN 4-OCF ₃ 0 HH SN (CH ₂ CH ₂ CH ₂ CH ₃ ) ₂ O 3-F 3,4-F ₂ 4-Cl ──── ───────────────────────────────

[0092]

[Table 58] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 HH SN (CH ₃ ) CO ₂ CH ₂ CH ₃ O 3-CF ₃ 4-CN 4-CF ₃ 0 H CH ₂ CH ₃ HO 3-F 4-F 4-Cl 0 H CH ₂ CH ₂ CH ₃ HO 3-F 4- F 4-Br 0 H CH ₂ CH ₂ CH ₂ CH ₃ HO 3-F 4-F 4-CF ₃ 0 H CH (CH ₃ ) ₂ HO 3-F 4-F 4-OCF ₃ 0 HC (CH ₃ ) ₃ HO 3-F 4-F 4-OCHF ₂ 0 H CH ₂ CH = CH ₂ HO 3-F 4-F 4-OCF ₂ Br 0 H CH ₂ C ≡ CH HO 3-F 4-F 4-OCF ₂ CHF ₂ 0 H CH ₂ OCH ₃ HO 3-F 4-F 4-OSO ₂ CF ₃ 0 H CH ₂ OCH ₂ CH ₃ HOH 4-F 4-OCF ₃ 0 H CH ₂ CH ₂ OCH ₃ HO 4-F 4 -F 4-Cl 0 H CHF ₂ HO 3-Cl 4-F 4-CF ₃ 0 H CBrF ₂ HO 3-Br 4-F 4-OCF ₃ 0 H CF ₃ HO 3-CF ₃ 4-F 4-Cl 0 H COCH ₃ HO 3-OCF ₃ 4-F 4-CF ₃ 0 H COCF ₃ HO 3-OCHF ₂ 4-F 4-OCF ₃ 0 H CO ₂ CH ₃ HO 4-OCHF ₂ 4-F 4-Cl 0 H CH ₂ C ₆ H ₅ HO 3-F 4-Cl 4-CF ₃ 0 H SC ₆ H ₅ HO 3-F 4-Br 4-OCF ₃ 0 H SCCl ₃ HO 3-F 4-CF ₃ 4-Cl 0 H SCO ₂ CH ₂ CH ₃ HO 3-F 4-OSO ₂ CF ₃ 4-CF ₃ 0 HS (C ₆ H ₄ -2-NO ₂ ) HO 3-F 4-CN 4-OCF ₃ 0 H SN ( _{CH 2 CH 2 CH 2 CH 3} ) 2 HO 3-F 3,4-F 2 4-Cl ─────── ───────────────────────────

[0093]

[Table 59] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 H SN (CH ₃ ) CO ₂ CH ₂ CH ₃ HO 3-CF ₃ 4-CN 4-CF ₃ 0 CH ₂ CH ₃ HHO 3-F 4-F 4-Cl 0 CH ₂ CH ₂ CH ₃ HHO 3-F 4-F 4-Br 0 CH ₂ CH ₂ CH ₂ CH ₃ HHO 3-F 4-F 4-CF ₃₀ CH (CH ₃ ) ₂ HHO 3-F 4-F 4-OCF ₃ 0 C (CH ₃ ) ₃ HHO 3-F 4-F 4-OCHF ₂ 0 Q1 HHO 3-F 4-F 4-OCF ₂ Br 0 Q4 HHO 3-F 4-F 4-OCF ₂ CHF ₂ 0 FHHO 3-F 4-F 4-OSO ₂ CF ₃ 0 Cl HHOH 4-F 4 -OCF ₃ 0 Br HHO 4-F 4-F 4-Cl 0 IHHO 3-Cl 4-F 4-CF ₃ 0 OH HHO 3-Br 4-F 4-OCF ₃ 0 CN HHO 3-CF ₃ 4-F 4-Cl 0 NO ₂ HHO 3-OCF ₃ 4-F 4-CF ₃ 0 CH ₂ FHHO 3-OCHF ₂ 4-F 4-OCF ₃ 0 CF ₃ HHO 4-OCHF ₂ 4-F 4-Cl 0 OCH ₃ HHO 3-F 4-Cl 4-CF ₃ 0 OCH ₂ CH ₃ HHO 3-F 4-Br 4-OCF ₃ 0 OCF ₃ HHO 3-F 4-CF ₃ 4-Cl 0 SCH ₃ HHO 3-F 4- OSO ₂ CF ₃ 4-CF ₃₀ SCF ₃ HHO 3-F 4-CN 4-OCF ₃ 0 SO ₂ CH ₃ HHO 3-F 3,4-F ₂ 4-Cl ─────────── ── ──────────────────────

[0094]

[Table 60] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 SO ₂ CF ₃ HHO 3-CF ₃ 4-CN 4-CF ₃ 0 OSO ₂ CF ₃ HHO 3-F 4-F 4-Cl 0 CO ₂ CH ₂ CH ₃ HHO 3-F 4-F 4-Br 0 CO ₂ CH ₃ HHO 3-F 4-F 4- CF ₃ 0 CH ₂ CO ₂ CH ₃ HHO 3-F 4-F 4-OCF ₃ 0 N (CH ₃ ) ₂ HHO 3-F 4-F 4-OCHF ₂ 0 C ₆ H ₅ HHO 3-F 4-F 4-OCF ₂ Br 0 C ₆ H ₄ -4-FHHO 3-F 4-F 4-OCF ₂ CHF ₂ 0 C ₆ H ₄ -4-Cl HHO 3-F 4-F 4-OSO ₂ CF ₃ 0 C ₆ H ₄ -4-Br HHOH 4-F 4-OCF ₃ 0 C ₆ H ₄ -4-CN HHO 4-F 4-F 4-Cl 0 C ₆ H ₄ -4-CF ₃ HHO 3-Cl 4- F 4-CF ₃ 0 CH ₂ C ₆ H ₅ HHO 3-Br 4-F 4-OCF ₃ 0 CH ₃ CH ₃ CH ₃ O 3-F 4-F 4-Cl 0 CH ₃ CH ₃ CH ₃ O 3- F 4-F 4-Br 0 CH ₃ CH ₃ CH ₃ O 3-F 4-F 4-CF ₃ 0 CH ₃ CH ₃ CH ₃ O 3-F 4-F 4-OCF ₃ 0 CH ₃ CH ₃ CH ₃ O 3-F 4-F 4-OCHF ₂₀ CH ₃ CH ₃ CH ₃ O 3-F 4-F 4-OCF ₂ Br 0 CH ₃ CH ₃ CH ₃ O 3-F 4-F 4-OCF ₂ CHF ₂ 0 CH ₃ CH ₃ CH ₃ O 3-F 4-F 4-OSO ₂ CF ₃ 0 CH ₃ CH ₃ CH ₃ OH 4-F 4-OCF ₃₀ CH ₃ CH ₃ CH ₃ O 4-F 4-F 4-Cl ──────────────────── ────────────────

[0095]

[Table 61] ─────────────────────────────────── k R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 CH ₃ CH ₃ CH ₃ O 3-Cl 4- F 4-CF ₃ 0 H CH ₂ OCH ₃ CH ₃ O 3-F 4-F 4-Cl 0 H COCH ₃ CH ₃ O 3-F 4-F 4-Br 0 H CO ₂ CH ₃ CH ₃ O 3- F 4-F 4-CF ₃ 0 H CHF ₂ CH ₃ O 3-F 4-F 4-OCF ₃ 0 H CH ₂ C ₆ H ₅ CH ₃ O 3-F 4-F 4-OCHF ₂ 0 H SC ₆ H ₅ CH ₃ O 3-F 4-F 4-OCF ₂ Br 0 H CH ₃ CH ₂ OCH ₃ O 3-F 4-F 4-OCF ₂ CHF ₂₀ H CH ₃ COCH ₃ O 3-F 4-F 4-OSO ₂ CF ₃ 0 H CH ₃ CO ₂ CH ₃ OH 4-F 4-OCF ₃ 0 H CH ₃ CHF ₂ O 4-F 4-F 4-Cl 0 H CH ₃ CH ₂ C ₆ H ₅ O 3 -Cl 4-F 4-CF ₃ 0 H CH ₃ SC ₆ H ₅ O 3-Br 4-F 4-OCF ₃ 0 CH ₃ CH ₃ CH ₂ OCH ₃ O 3-CF ₃ 4-F 4-Cl 0 CH ₃ CH ₃ COCH ₃ O 3-OCF ₃ 4-F 4-CF ₃ 0 CH ₃ CH ₃ CO ₂ CH ₃ O 3-OCHF ₂ 4-F 4-OCF ₃ 0 CH ₃ CH ₃ CHF ₂ O 4-OCHF ₂ 4-F 4-Cl 0 CH ₃ CH ₃ CH ₂ C ₆ H ₅ O 3-F 4-Cl 4-CF ₃ 0 C ₆ H ₅ CH ₃ SC ₆ H ₅ O 3-F 4-Br 4-OCF ₃ 0 Br CH ₃ CH ₃ O 3-F 4-CF ₃ 4-Cl 0 CN CH ₃ CH ₃ O 3-F 4-OSO ₂ CF ₃ 4-CF ₃ 0 OH CH ₃ CH ₃ O 3-F 4-CN 4-OCF ₃ 0 C ₆ H ₅ CH ₃ CH ₃ O 3-F 3,4-F ₂ 4-Cl ─────────────────────────────────── ─

[0096]

[Table 62] ─────────────────────────────────── k R ¹ R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 0 CH ₂ C ₆ H ₅ CH ₃ CH ₃ O 3-CF ₃ 4-CN 4-CF ₃ 1 HHHHO 3-F 4-F 4-Cl 1 HHHHO 3-F 4-F 4-Br 1 HHHHO 3-F 4-F 4-CF ₃ 1 HHHHO 3- F 4-F 4-OCF ₃ 1 HHHHO 3-F 4-F 4-OCHF ₂ 1 HHHHO 3-F 4-F 4-OCF ₂ Br 1 HHHHO 3-F 4-F 4-OCF ₂ CHF ₂ 1 HHHHO 3 -F 4-F 4-OSO ₂ CF ₃ 1 HHHHOH 4-F 4-OCF ₃ 1 HHHHO 4-F 4-F 4-Cl 1 HHHHO 3-Cl 4-F 4-CF ₃ 1 HHHHO 3-Br 4- F 4-OCF ₃ 1 HHHHO 3-CF ₃ 4-F 4-Cl 1 HHHHO 3-OCF ₃ 4-F 4-CF ₃ 1 HHHHO 3-OCHF ₂ 4-F 4-OCF ₃ 1 HHHHO 4-OCHF ₂ 4 -F 4-Cl 1 HHHHO 3-F 4-Cl 4-CF ₃ 1 HHHHO 3-F 4-Br 4-OCF ₃ 1 HHHHO 3-F 4-CF ₃ 4-Cl 1 HHHHO 3-F 4-OSO ₂ CF ₃ 4-CF ₃ 1 HHHHO 3-F 4-CN 4-OCF ₃ 1 HHHHO 3-F 3,4-F ₂ 4-Cl ─────────────────── ─────────────────

[0097]

[Table 63] ─────────────────────────────────── k R ¹ R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 1 HHHHO 3-CF ₃ 4-CN 4- CF ₃ 1 CH ₃ HHHO 3-F 4-F 4-Cl 1 CH ₃ HHHO 3-F 4-F 4-Br 1 CH ₃ HHHO 3-F 4-F 4-CF ₃ 1 CH ₃ HHHO 3-F 4 -F 4-OCF ₃ 1 CH ₃ HHHO 3-F 4-F 4-OCHF ₂ 1 CH ₃ HHHO 3-F 4-F 4-OCF ₂ Br 1 CH ₃ HHHO 3-F 4-F 4-OCF ₂ CHF ₂ 1 CH ₃ HHHO 3-F 4-F 4-OSO ₂ CF ₃ 1 CH ₃ HHHOH 4-F 4-OCF ₃ 1 CH ₃ HHHO 4-F 4-F 4-Cl 1 CH ₃ HHHO 3-Cl 4- F 4-CF ₃ 1 CH ₃ HHHO 3-Br 4-F 4-OCF ₃ 1 CH ₃ HHHO 3-CF ₃ 4-F 4-Cl 1 CH ₃ HHHO 3-OCF ₃ 4-F 4-CF ₃ 1 CH ₃ HHHO 3-OCHF ₂ 4-F 4-OCF ₃ 1 CH ₃ HHHO 4-OCHF ₂ 4-F 4-Cl 1 CH ₃ HHHO 3-F 4-Cl 4-CF ₃ 1 CH ₃ HHHO 3-F 4- Br 4-OCF ₃ 1 CH ₃ HHHO 3-F 4-CF ₃ 4-Cl 1 CH ₃ HHHO 3-F 4-OSO ₂ CF ₃ 4-CF ₃ 1 CH ₃ HHHO 3-F 4-CN 4-OCF _{3 1 CH 3 HHHO 3-F 3,4} -F 2 4-Cl ──────────────────────── ──────────

[0098]

[Table 64] ─────────────────────────────────── k R ¹ R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 1 CH ₃ HHHO 3-CF ₃ 4-CN 4-CF ₃ 1 CH ₂ CH ₃ HHHO 3-F 4-F 4-Cl 1 CH ₂ CH ₂ CH ₃ HHHO 3-F 4-F 4-Br 1 CH ₂ CH ₂ CH ₂ CH ₃ HHHO 3-F 4 -F 4-CF ₃ 1 CH (CH ₃ ) ₂ HHHO 3-F 4-F 4-OCF ₃ 1 C (CH ₃ ) ₃ HHHO 3-F 4-F 4-OCHF ₂ 1 CH ₂ CH = CH ₂ HHHO 3-F 4-F 4-OCF ₂ Br 1 CH ₂ C ≡ CH HHHO 3-F 4-F 4-OCF ₂ CHF ₂ 1 CH ₂ OCH ₃ HHHO 3-F 4-F 4-OSO ₂ CF ₃ 1 CH ₂ OCH ₂ CH ₃ HHHOH 4-F 4-OCF ₃ 1 CH ₂ CH ₂ OCH ₃ HHHO 4-F 4-F 4-Cl 1 CHF ₂ HHHO 3-Cl 4-F 4-CF ₃ 1 CBrF ₂ HHHO 3- Br 4-F 4-OCF ₃ 1 CF ₃ HHHO 3-CF ₃ 4-F 4-Cl 1 COCH ₃ HHHO 3-OCF ₃ 4-F 4-CF ₃ 1 COCF ₃ HHHO 3-OCHF ₂ 4-F 4- OCF ₃ 1 CO ₂ CH ₃ HHHO 4-OCHF ₂ 4-F 4-Cl 1 CH ₂ C ₆ H ₅ HHHO 3-F 4-Cl 4-CF ₃ 1 SC ₆ H ₅ HHHO 3-F 4-Br 4- OCF ₃ 1 SCCl ₃ HHHO 3-F 4-CF ₃ 4-Cl 1 SCO ₂ CH ₂ CH ₃ HHHO 3-F 4-OSO ₂ CF ₃ 4-CF ₃ 1 S (C ₆ H ₄ -2-NO ₂ ) HHHO 3-F 4-CN 4-OCF ₃ 1 SN (CH ₂ CH ₂ CH ₂ CH ₃ ) ₂ HHHO 3-F 3,4-F ₂ 4-Cl ── ──────────────────────────────────

[0099]

[Table 65] ─────────────────────────────────── k R ¹ R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 1 SN (CH ₃ ) CO ₂ CH ₂ CH ₃ HHHO 3-CF ₃ 4-CN 4-CF ₃ 2 HHHHO 3-F 4-F 4-Cl 2 HHHHO 3-F 4-F 4-Br 2 HHHHO 3-F 4-F 4-CF ₃ 2 HHHHO 3 -F 4-F 4-OCF ₃ 2 HHHHO 3-F 4-F 4-OCHF ₂ 2 HHHHO 3-F 4-F 4-OCF ₂ Br 2 HHHHO 3-F 4-F 4-OCF ₂ CHF ₂ 2 HHHHO 3-F 4-F 4-OSO ₂ CF ₃ 2 HHHHOH 4-F 4-OCF ₃ 2 HHHHO 4-F 4-F 4-Cl 2 HHHHO 3-Cl 4-F 4-CF ₃ 2 HHHHO 3-Br 4 -F 4-OCF ₃ 2 HHHHO 3-CF ₃ 4-F 4-Cl 2 HHHHO 3-OCF ₃ 4-F 4-CF ₃ 2 HHHHO 3-OCHF ₂ 4-F 4-OCF ₃ 2 HHHHO 4-OCHF ₂ 4-F 4-Cl 2 HHHHO 3-F 4-Cl 4-CF ₃ 2 HHHHO 3-F 4-Br 4-OCF ₃ 2 HHHHO 3-F 4-CF ₃ 4-Cl 2 HHHHO 3-F 4-OSO ₂ CF ₃ 4-CF ₃ 2 HHHHO 3-F 4-CN 4-OCF ₃ 2 HHHHO 3-F 3,4-F ₂ 4-Cl ────────────────── ──────────────────

[0100]

[Table 66] ─────────────────────────────────── k R ¹ R ² R ³ R ⁴ WX _l Y _m Z _n ─────────────────────────────────── 2 HHHHO 3-CF ₃ 4-CN 4- CF ₃ ───────────────────────────────────

In the present invention, the pest control agent means especially a pest control 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 semicarbazone derivative, and a typical production method will be specifically described below.

In each method (method A to method D), W, X,
Y, Z, R ¹ , R ² , R ³ , R ⁴ , k, l, m and n have the same meanings as described above, L ¹ is a chlorine atom, a bromine atom,
It shows a good leaving group such as an iodine atom, an alkyl sulfonate group or an aryl sulfonate group.

Method A

[0105]

[Chemical 6]

Compound [II] is reacted with phosphorus pentachloride in an inert solvent or without a solvent, or compound [I]
Compound [III] is obtained by reacting I] with triphenylphosphine and carbon tetrachloride. Then, the compound [III] and the compound [IV] are reacted in the presence or absence of a base in an inert solvent to give the compound [V] of the present invention (R ² in the compound [I] is a hydrogen atom). can get. Furthermore, the compound [I] of the present invention can be obtained by reacting the compound [V] of the present invention with the compound [VI] in the presence of a base and in an inert solvent.

Examples of the solvent when phosphorus pentachloride is used in step 1 include aromatic hydrocarbons such as benzene and toluene, and halogenated hydrocarbons such as carbon tetrachloride and 1,1,2-trichloroethane. Generally, it is preferred to use a slight excess of phosphorus pentachloride without solvent. The reaction temperature can be set to any temperature from 0 ° C to the reflux temperature of the reaction mixture, but is preferably 60 ° C to the reflux temperature.
When triphenylphosphine and carbon tetrachloride are used, it is preferable to use equimolar to small excess of triphenylphosphine and large excess of carbon tetrachloride at the reflux temperature of the reaction mixture.

As the base used in the step 2, alkali metal alkoxides such as sodium ethoxide and potassium tert-butoxide, sodium hydroxide,
Alkali metal hydroxides such as potassium hydroxide, alkali metal carbonates such as sodium carbonate, potassium carbonate and sodium hydrogen carbonate, alkali metal hydrides such as sodium hydride and potassium hydride, organic bases such as triethylamine and pyridine, etc. Can be mentioned. Any solvent may be used as long as it does not inhibit the progress of the reaction. For example, lower alcohols such as methanol and ethanol, aromatic hydrocarbons such as benzene and toluene, diethyl ether, 1,
2-dimethoxyethane, tetrahydrofuran, 1,4-
Ethers such as dioxane, dichloromethane, 1,2-
Examples thereof include halogenated hydrocarbons such as 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 an organic base such as triethylamine or pyridine as the base, and an aromatic hydrocarbon such as benzene or toluene or an ether such as tetrahydrofuran or diethyl ether as the solvent. 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 50 ° C.

As the base used in the step 3, alkali metal alkoxides such as sodium ethoxide and potassium tert-butoxide, sodium hydroxide,
Alkali metal hydroxides such as potassium hydroxide, alkali metal carbonates such as sodium carbonate, potassium carbonate and sodium hydrogen carbonate, alkali metal hydrides such as sodium hydride and potassium hydride, organic bases such as triethylamine and pyridine, etc. Can be mentioned. Any solvent may be used as long as it does not inhibit the progress of the reaction. For example, lower alcohols such as methanol and ethanol, aromatic hydrocarbons such as benzene and toluene, diethyl ether, 1,
2-dimethoxyethane, tetrahydrofuran, 1,4-
Ethers such as dioxane, dichloromethane, 1,2-
Examples thereof include halogenated hydrocarbons such as 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.

Method B

[0111]

[Chemical 7]

Compound [II] as the starting material is compound [VII]
And compound [VIII] in the presence of a base in an inert solvent. Examples of the base used in this method include alkali metal carbonates such as sodium carbonate, potassium carbonate and sodium hydrogen carbonate, alkali metal hydrides such as sodium hydride and potassium 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, aromatic hydrocarbons such as benzene and toluene,
Ethers such as diethyl ether, 1,2-dimethoxyethane, tetrahydrofuran, 1,4-dioxane, halogenated hydrocarbons such as dichloromethane and 1,2-dichloroethane, amides such as dimethylformamide and dimethylacetamide, acetonitrile, dimethyl Examples include 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 the base, and an aromatic hydrocarbon such as benzene or toluene or an ether such as tetrahydrofuran or diethyl ether as the solvent.
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 50 ° C.

Method C

[0114]

[Chemical 8]

This method is a method for synthesizing a starting material (R ³ = R ⁴ = hydrogen atom of compound [IV]) when R ³ = R ⁴ = hydrogen atom. Compound [XI] is obtained by reacting compound [IX] with compound [X] in the presence or absence of a catalyst in an inert solvent. Examples of the catalyst used in this reaction include organic bases such as triethylenediamine and diazabicycloundecene. The amount of the catalyst used can be set to any amount from 0.001% by weight to 10% by weight with respect to the compound [X], but 0.1% by weight to 1% by weight.
Weight percent is preferred. Any solvent may be used as long as it does not inhibit the progress of the reaction, and examples thereof include aromatic hydrocarbons such as benzene and toluene, ethers such as diethyl ether and tetrahydrofuran, halogenated hydrocarbons such as dichloromethane and chloroform, and dimethylformamide. , Amides such as dimethylacetamide, acetonitrile, dimethylsulfoxide, water and the like. These inert solvents may be used alone or in a mixture. 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 50 ° C. In this reaction, the molar ratio of the reactants is not particularly limited, but the compound [X
In order to obtain I] in good yield, it is preferable to use the compound [IX] in a slight excess with respect to the compound [X].

Method D

[0117]

[Chemical 9]

This method is an alternative to the method C and is a method for synthesizing a starting material (R ³ = R ⁴ = hydrogen atom of compound [IV]) when R ³ = R ⁴ = hydrogen atom. Compound [XIII] is obtained by reacting compound [XII] with compound [X] in the presence or absence of a catalyst in an inert solvent. The reaction conditions such as catalyst, solvent and temperature used in this reaction are the same as those in Method C. In this method, equimolar amounts of compound [XII] and compound [X] are used to yield compound [XII] in good yield.
The feature is that I] can be obtained. In step 2, compound [XIII] can be reacted in the presence of an acid in an inert solvent to give compound [XI]. Examples of the acid used include inorganic acids such as hydrochloric acid and sulfuric acid, organic acids such as paratoluenesulfonic acid and trifluoroacetic acid, and the like. Any solvent may be used as long as it does not hinder the progress of the reaction, and examples thereof include lower alcohols such as methanol and ethanol, aromatic hydrocarbons such as benzene and toluene, ethers such as diethyl ether and tetrahydrofuran, dichloromethane, and four. Examples thereof include halogenated hydrocarbons such as carbon chloride, amides such as dimethylformamide and dimethylacetamide, acetonitrile, dimethylsulfoxide, acetic acid and water. These inert solvents may be used alone or in a mixture. Generally, it is preferable to use an excess amount of hydrochloric acid in a lower alcohol such as methanol or ethanol. 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 the reflux temperature of the reaction mixture.

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 to it.

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, generally, a suitable carrier, for example, solid carrier such as clay, talc, bentonite, diatomaceous earth, white carbon or water, alcohols (isopropanol, butanol, benzyl alcohol) is used. , 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, if necessary, may be used as a herbicide of other species, various insecticides, acaricides at the time of formulation or spraying.
It may be mixed and applied with nematicides, fungicides, plant growth regulators, synergists, fertilizers, soil conditioners and the like.

Particularly, when mixed with other agricultural chemicals 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. The types of pesticides used in combination with the compound of the present invention include, for example, Farm Chemicals Handbook (Farm Chemi
cals Handbook) Compounds described in the 1993 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.

[0125] 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 99.99 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

[0132]

【Example】

Examples (Synthesis Examples, Formulation Examples, Test Examples) The present invention will be specifically described below 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 N- (4-chlorophenyl) -4-chlorobenzamido-4-trifluoromethoxyphenylsemicarbazone
(Inventive Compound No. 1) 1.0 g of N- (4-chlorophenyl) -4-chlorobenzamide and 1.2 g of phosphorus pentachloride are gradually dissolved by heating,
After stirring under reflux for 3 hours, by-produced phosphorus oxychloride was distilled off under reduced pressure. Residue and N- (4-trifluoromethoxyphenyl) hydrazinecarboxamide 1.00
g was dissolved in a mixed solvent of 20 ml of benzene and 20 ml of tetrahydrofuran, 0.50 g of triethylamine was added dropwise with stirring at room temperature, and the mixture was further stirred at room temperature for 3 hours. The reaction mixture was added to 200 ml of ice water, and ethyl acetate 1 was added.
00 ml was added for extraction. The organic layer was washed with water, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 2.05 g of a crude product. This was purified by preparative thin layer chromatography and then recrystallized from isopropyl ether to obtain 0.38 g of the desired product. ¹ HNMR (CDCl ₃ + DMSO d-6, TM
S, δ ppm): 6.50-7.65 (12H, m), 8.08 (1H, s), 8.41 (1
H, s), 9.51 (1H, s).

Reference Example 1 N- (4-chlorophenyl) -4-chlorobenzamide 3.3 g of 4-chloroaniline and 3.3 of triethylamine.
g was dissolved in 50 ml of benzene, and 4-
Chlorobenzoyl chloride 5.3 g benzene solution 2
After dropping 0 ml, the mixture was further stirred at room temperature for 1 hour. After adding the reaction mixture to 200 ml of ice water, ethyl acetate 20
Extracted with 0 ml. The organic layer was washed with 1N hydrochloric acid and then with saturated saline, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 6.33 g of N- (4-chlorophenyl) -4-chlorobenzamide. .

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

Table 2

[0138]

[Chemical 10]

[0139]

[Table 67] ─────────────────────────────────── No. k R ¹ R ² R ³ R ⁴ WX _l Y _m Z _n Melting point ─────────────────────────────────── 1 0 HHHO 4-Cl 4- Cl 4-OCF ₃ 206.5-208.0 2 1 HHHHO 4-Cl 4-Cl 4-OCF ₃ 185.0-187.0 3 0 HHHO 3-Cl 4-F 4-OCF ₃ 182.0-183.0 4 0 HHHO 3-Cl 4-CN 4 -OCF ₃ 198.0-200.0 5 0 HHHO 3-F 4-CN 4-OCF ₃ 193.0-195.5 6 1 HHHHO 3-CF ₃ 4-F 4-OCF ₃ 166.0-167.0 7 0 HHHO 4-CF ₃ 4-F 4 -OCF ₃ 183.0-185.5 8 1 HHHHO 3-CF ₃ 4-F 4-OCF ₃ 166.0-167.0 9 0 HHHO 3-CF ₃ 4-CN 4-OCF ₃ 210.0-212.5 10 0 HHHO 3-CF ₃ 4-CF ₃ 4-OCF ₃ 162.0-163.0 11 0 HHHO 3-OCF ₃ 4-CN 4-OCF ₃ 199.5-202.5 ────────────────────────── ──────────

[Formulation Example] Next, a formulation example of a pest controlling agent containing the compound of the present invention as an active ingredient is 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: Trade name of Kuraray Isoprene Chemical Co., Ltd. Vanillex N ........ 5 parts (Anionic surfactant: Trade name of Sanyo Kokusaku Pulp Co., Ltd.) 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 parts (White carbon: Shionogi & 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 controlling agent will be specifically described in the following test examples.

Test Example 1 Insecticidal test against Spodoptera litura A 5% emulsion of the compound of the present invention described in the specification (25% wettable powder depending on the compound was used as a test) was diluted with water containing a spreader to give 1000 ppm. Prepare a chemical solution of the concentration, immerse kanran leaves in this chemical solution for about 10 seconds, air-dry and put it in a petri dish, in which 10 second-infested larvae of Spodoptera litura are released per petri dish with a perforated lid. And stored in a constant temperature 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 rate (%) = (number of dead insects / number of released insects) × 100

As a result, the following compounds showed 100% mortality. Inventive compound: No. 3, 4, 5, 6, 9, 10, 1
1.

Test Example 2 Insecticidal test against pearl oyster ladybird A 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 spreading agent. Then, prepare a chemical solution with a concentration of 1000 ppm, soak the tomato leaves in this chemical solution for about 10 seconds, air-dry and place in a petri dish.
Ten of the insects were released, covered and placed in a thermostatic chamber at 25 ° C, and the mortality rate after 6 days was calculated from the following formula. The test is 2
It was done in a ward system.

Mortality rate (%) = (number of dead insects / number of released insects) × 100

As a result, the following compounds showed 100% mortality. Inventive compound: No. 1, 2, 3, 4, 5, 6, 8,
9, 10, 11.

[0155]

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 (51) Int.Cl. ⁶ Identification code Office reference number FI Technical display location C07C 317/38 7419-4H 317/44 7419-4H 323/31 7419-4H 323/62 7419-4H 337/08 7106-4H C07D 317/46 319/18 319/20 (72) Inventor Akira Numata 1 722 Tsuboi-cho, Funabashi City, Chiba Prefecture, Central Research Laboratory, Nissan Chemical Industries, Ltd. (72) Tomoyuki Ogura Funabashi, Chiba Prefecture 1 722, Tsuboi-cho, Tsuboi-shi, Nissan Central Chemical Research Institute (72) Inventor Toshiro Miyake 1470 Shiraoka, Shiraoka-cho, Minami Saitama-gun, Saitama Prefecture Bioscience Research Institute, Nissan Chemical Industries, Ltd. (72) Akihiko Fujita Minami-Saitama-gun, Saitama Prefecture 1470 Shiraoka, Shiraoka-cho Nissan Chemical Industry Co., Ltd., Institute of Biological Sciences (72) Inventor Norihiko Mimori 1470, Shiraoka, Shiraoka-cho, Minamisaitama-gun, Saitama Nissan Chemical Co., Ltd. Company Biological Sciences in the Institute (72) inventor Takii new self Saitama Prefecture Minami-Saitama District Shiraoka-cho Oaza Shiraoka 1470 Nissan Chemical Industry Co., Ltd. Biological Sciences in the Institute

Claims (4)

[Claims] 1. A compound represented by the general formula [I]: [In the formula, W represents an oxygen atom or a sulfur atom, and X, Y, and Z are each independently a halogen atom, a hydroxyl group, a cyano group, a nitro group, an SCN group, a trimethylsilyl group,
R ⁹ , OR ⁹ , S (O) _p R ⁹ group, OS (O) ₂ R ⁹ group, O
C (O) R ⁹ group, C (O) R ⁹ group, CO ₂ R ⁹ group, C (O)
N (R ⁹ ) R ¹⁰ group, SO ₂ N (R ⁹ ) R ¹⁰ group, NHC
(O) R ⁹ group, N (R ⁹ ) R ¹⁰ group, —CH═CH—CH═CH— group formed between adjacent carbon atoms, —OCH ₂ O
- group, -OCH ₂ CH ₂ O- group, -OCF ₂ O-groups, -O
CF ₂ CF ₂ O- group or -OCF ₂ CF ₂ - represents a group, R ¹ represents the hydrogen atom, R ^5, which may be substituted by R ⁵ C ₁ ~C ₆ alkyl group or (R ⁵⁾ _q Represents a phenyl group which may be substituted, and R ² , 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. , A C ₁ -C ₆ haloalkyl group, a C ₂ -C ₆ alkoxyalkyl group, a C ₂ -C ₆ alkylcarbonyl group, a C ₂ -C ₆ alkoxycarbonyl group, a C ₂ -C ₆ haloalkylcarbonyl group, C ₁ -C ₆ alkylthio group, C ₁ -C ₆ haloalkylthio ^{group, R 6 OC (O) N} (R 7) S- group, R ⁷ (R ⁸⁾ NS
A group or a benzyl group which may be substituted by (R ⁵ ) _q , wherein R ⁵ is a halogen atom, a hydroxyl group, a cyano group, a nitro group, C ₁
To C ₆ alkyl group, C _{1 to} C ₆ haloalkyl group, C _{1 to} C ₆
Alkoxy groups, C ₁ -C ₆ haloalkoxy group, C ₁ -C ₆ alkylthio group, C ₁ -C ₆ haloalkylthio group, C ₁ -C ₆
An alkylsulfonyl group, a C ₁ -C ₆ haloalkylsulfonyl group, a C ₂ -C ₆ alkoxycarbonyl group, an amino group or a di C ₁ -C ₆ alkylamino group, wherein R ⁶ , R ⁷ and R ⁸ are each independently A C ₁ -C ₆ alkyl group,
(R ⁵⁾ a phenyl group or optionally substituted by _q (R ⁵⁾ shows a benzyl group which may be substituted by _q, R ⁹ is C ₁ -C ₆ alkyl group, C ₁ -C ₆ haloalkyl group ,
C ₂ -C ₆ alkenyl groups, C ₂ -C ₆ haloalkenyl groups, C
₂ -C ₆ alkynyl group, C ₂ -C ₆ haloalkynyl group, C ₃
To C ₆ cycloalkyl group, C _{3 to} C ₆ halocycloalkyl group, C _{4 to} C ₇ cycloalkylalkyl group, C _{2 to} C ₆ alkoxyalkyl group, C _{2 to} C ₆ alkylthioalkyl group,
C ₂ -C ₆ alkoxycarbonyl group, C ₂ -C ₆ cyanoalkyl radical, (R ⁵⁾ a phenyl group optionally substituted by _q, (R ⁵⁾ Good benzyl group or optionally substituted by _q ( R ⁵ ) represents a pyridyl group optionally substituted by _r , R ¹⁰ represents a hydrogen atom or a C ₁ -C ₆ alkyl group, k represents an integer of 0 to 2, and l represents an integer of 0 to 5 ( Provided that when 1 is 2 to 5, X may be the same or different, and m is an integer of 0 to 5 (provided that when m is 2 to 5, Y is the same or different). N is an integer of 1 to 5 (however, when n is 2 to 5, Z may be the same or different), and p is an integer of 0 to 2. , q is an integer of 0 to 5 (provided that when R ⁵ of q is 2 to 5 be different even in the same Indicates have), r denotes 0 to 4 integer (provided that when r is 2 to 4 R ⁵ may be different even in the same). ] The semicarbazone compound represented by these. 2. W is an oxygen atom, X is a halogen atom, C₁~ C₆Alkyl group, C₁~ C₆Ha
Lower alkyl group, C₁~ C₆Haloalkoxy group, C₁~ C₆Ha
Low alkylthio group or C₁~ C₆Haloalkylsulfoni
Is a halogen atom, cyano group, nitro group, C₁~ C₆A
Rukiru group, C₁~ C₆Haloalkyl group, C₁~ C₆Arcoki
Shi group, C₁~ C₆Haloalkoxy group, C₁~ C₆Alkylchi
O group, C₁~ C₆Haloalkylthio group, C₁~ C₆Alkyl
Sulfonyl group, C₁~ C₆Haloalkylsulfonyl group, C
₁~ C₆Haloalkylsulfonyloxy group, adjacent carbon
-OCF formed between atoms₂O-group or -OCF₂CF
₂Represents an O- group, Z represents a halogen atom, a cyano group, a nitro group, C₁~ C₆Ha
Lower alkyl group, C₁~ C₆Haloalkoxy group, C₁~ C₆A
Rukiruthio group, C₁~ C₆Haloalkylthio group, C₁~ C₆
Alkylsulfinyl group, C₁~ C₆Haloalkyl sulf
Inyl group, C ₁~ C₆Alkylsulfonyl group, C₁~ C₆Ha
Roalkylsulfonyl group, C₁~ C₆Alkylsulfonyl
Oxy group, C₁~ C₆A haloalkylsulfonyloxy group,
-OCF formed between adjacent carbon atoms₂O-group, -O
CF₂CF₂O-group or -OCF₂CF₂Represents a group, R¹, R², R³, R^FourAre each independently a hydrogen atom or C₁
~ C₆Represents an alkyl group, l and m each independently represent an integer of 0 to 2, and n is 1
The semicarbazone compound according to claim 1, which represents an integer of 3 to 3.
Stuff. 3. A pest control agent containing, as an active ingredient, one or more of the semicarbazone compounds according to claim 1. 4. A pest control agent containing, as an active ingredient, one or more of the semicarbazone compounds according to claim 2.