JPH107659A - Oxime, hydrazone or azin derivative and insecticide - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject compound having strong effects against resistant insect pest and properties giving no harmful influence to men and beasts and the environment and extraordinary excellent insecticidal activities as an effective ingredient in insecticides. SOLUTION: This compound is expressed by formula I [a condensed ring in formula II is tetralin, coumarone, benzodioxane; R<1> is a halogen, a 1-6C alkyl, a 1-6C alkoxy or phenyl; R<2> is a halogen, a 1-6C alkyl, a 1-6C alkoxy, a 1-6C alkylthio, cyano, etc.; R<3> is a group of OR<5> (R<5> is H, a 1-6C alkyl, etc.), etc.; (m) is 0-4; (n) is 0-3; W is CH or N], e.g. (Z)-1-(O-isopropyl-6- tetralincarbohydroximoyl)-1H-1,2,4-triazole, etc., are cited. The compound of formula I is obtained by a known method using a carboxylic acid of formula III as a raw material. The compound is able to transmigrate from the surface to the back of a leaf.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to oxime, hydrazone or azine derivatives having insecticidal activity and salts thereof.

[0002]

2. Description of the Related Art As described in, for example, JP-A-1-308260 and International Publication WO9209581, it is known that certain oxime derivatives already have insecticidal activity. However, the above publication does not disclose any oxime, hydrazone or azine derivative of the present invention.

[0003]

In recent years, existing insecticides,
For example, pests exhibiting resistance to organophosphorus agents, carbamate agents, pyrethroid agents and the like have increased, making it difficult to control them. Therefore, a new type of insecticide which has a high effect on these resistant pests and has no harm to humans, livestock, beneficial insects, environment and the like is desired.

The present inventors have synthesized various oxime, hydrazone or azine derivatives and studied the biological activities thereof. As a result, the compounds of the present invention have extremely excellent insecticidal activity against various harmful insects. Heading that
The present invention has been completed.

[0005]

That is, the present invention provides a compound represented by the following general formula (I):

[0006]

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In the above formula, the formula

[0008]

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The following condensed ring group (condensed ring group)

[0010]

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(Wherein R ⁴ is a hydrogen atom, C 1 -C ³
Represents an alkyl group or a C2-C6 acyl group;
Or 2. ) Represents one fused ring selected from
¹ is a halogen atom, a C1-C6 alkyl group, C1-C6
R ² represents a halogen atom, a C1-C6 alkyl group (the alkyl group is 1 to 5),
Halogen atoms, one C1-C6 alkoxy group,
C1 to C6 alkylthio groups, which may be substituted by one C1 to C6 alkylsulfinyl group or one C1 to C6 alkylsulfonyl group), a C1 to C6 alkoxy group (the alkoxy group is 1 to 5 , A C1-C6 alkylthio group, a cyano group, a nitro group, a formyl group, a hydroxyl group or an amino group (the amino group is substituted by one or two C1-C3 alkyl groups). R ³ is a group represented by OR ⁵ , a group represented by NR ⁶ R ⁷ , or N =
CR ⁸ represents a group represented by R ⁹ , wherein R ⁵ is a hydrogen atom, C 1
-C6 alkyl group—the alkyl group has 1 to 5 halogen atoms, 1 or 2 hydroxyl groups, 1 C1 to C6 alkoxy group, 1 C1 to C6 alkylthio group, 1 C
2-C6 alkoxycarbonyl group, one phenyl group (the phenyl group is a C1-C3 alkyl group, a halogen atom, a C2-C6 alkoxycarbonyl group and a C2-C6
A 5- or 6-membered heterocyclic group (the heterocyclic group may be an oxygen atom, a sulfur atom, 1 to 3 atoms arbitrarily selected from nitrogen atoms, which may be substituted with 1 to 3 C1 to C3 alkyl groups, halogen atoms or oxo groups), 1 C3 to C6 cyclo An alkyl group (the cycloalkyl group may be substituted by 1 to 3 C1 to C3 alkyl groups, a halogen atom or an oxo group) or 1 C3 to C6 cycloalkenyl group (the cycloalkenyl group is 1 to 3 May be substituted by three C1-C3 alkyl groups, which may be substituted with a halogen atom or an oxo group), and a C2-C6 alkenyl group (wherein the alkenyl group is 1
Or two or three halogen atoms), a C2-C6 alkynyl group (the alkynyl group may be
Or a C3-C6 cycloalkyl group (the cycloalkyl group may be substituted with one to three C1-C3 alkyl groups, a halogen atom or an oxo group) ), C3 ~
C6 cycloalkenyl group (the cycloalkenyl group is 1
3 to 3 C1-C3 alkyl groups, which may be substituted by halogen atoms or oxo groups), C2-C6 acyl groups, C2-C6 alkoxycarbonyl groups, carbamoyl groups (the nitrogen atoms of the carbamoyl groups are C1-C6 A 5- or 6-membered heterocyclic group (optionally substituted by an alkyl group), which has 1 to 3 atoms arbitrarily selected from an oxygen atom, a sulfur atom and a nitrogen atom ,
R ⁶ and R ⁷ may be the same or different and represent a hydrogen atom or a C 1 -C 6 alkyl group, or may be substituted with 1 to 3 C 1 -C 3 alkyl groups, halogen atoms or oxo groups, or R ⁶ and R ⁷ may form a cyclic amino group together with an adjacent nitrogen atom, and R ⁸ and R ⁹ may be a hydrogen atom, a C1-C6 alkyl group or a phenyl group (the phenyl group may be M may represent 0, 1, 2, 3 or 4 (m may be 2, 3 or 4), and may be substituted with 1 to 5 substituents arbitrarily selected from a C3 alkyl group and a halogen atom. In the case of 4, each R ¹ may be the same or different), and n represents 0, 1, 2 or 3 (when n is 2 or 3, each R ² is the same or different W may represent CH or N. Or a salt thereof.

In the present invention, “halogen atom” is
They are a fluorine atom, a chlorine atom, a bromine atom and an iodine atom. R ¹
Is preferably a fluorine atom. R ² is preferably a fluorine atom, a chlorine atom or a bromine atom. R ² C
In the substituent of the 1-C6 alkyl group, it is preferably a fluorine atom. In the substituents of C1~C6 alkoxy group R ^2, preferably a fluorine atom. In the substituent of C1~C6 alkyl group R ^5, preferably a fluorine atom. R
^The substituent on the phenyl group of the C1-C6 alkyl group substituted by the phenyl group ⁵ is preferably a fluorine or chlorine atom. In the substituent of 5 or 6 membered heterocyclic group portion of C1~C6 alkyl group 5 or 6-membered heterocyclic group for R ⁵ is substituted, preferably a fluorine atom or a chlorine atom.
C1~C the C3~C6 cycloalkyl group for R ⁵ is substituted
The substituent in the C3 to C6 cycloalkyl group of the 6 alkyl group is preferably a fluorine atom or a chlorine atom. R
C1-C6 substituted by ⁵ C3-C6 cycloalkenyl groups
The substituent in the C3-C6 cycloalkenyl group of the 6-alkyl group is preferably a fluorine atom or a chlorine atom.
In the substituents of C2~C6 alkenyl groups R ^5, preferably a fluorine atom or a chlorine atom. Place in a substituent C2~C6 alkynyl group R ^5, preferably a fluorine atom or a chlorine atom. In the substituents of C3~C6 cycloalkyl group R ^5, preferably a fluorine atom or a chlorine atom.
In the substituents of C3~C6 cycloalkenyl group R ^5, preferably a fluorine atom or a chlorine atom. In the substituent of the 5- or 6-membered heterocyclic group for R ⁵ , it is preferably a fluorine atom or a chlorine atom. In the substituent of the phenyl group of R ⁸ or R ⁹ , it is preferably a fluorine atom or a chlorine atom.

The "C1-C6 alkyl group" includes, for example,
Methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, 2-methylbutyl, neopentyl, 1-ethylpropyl, n-hexyl, 4-methylpentyl, 3-methylpentyl, 2-methylpentyl, 1-methylpentyl, 3,3-dimethylbutyl, 2,2-dimethylbutyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, It is a linear or branched alkyl group having 1 to 6 carbon atoms, such as 2,3-dimethylbutyl and 2-ethylbutyl. In R ^1, preferably a methyl, ethyl, n- butyl, i- propyl, n- butyl, s- methyl, t- butyl, and most preferably methyl, ethyl, t- butyl. R ² is preferably methyl, ethyl, n-butyl, i-propyl, and more preferably methyl. In R ⁵ , preferably ethyl, n-propyl, i-propyl, n
-Butyl, s-butyl, most preferably i-propyl. C1~C nitrogen atom of carbamoyl group R ⁵
In the substituent of the 6 alkyl group, it is preferably methyl. In R ⁶ or R ⁷ , it is preferably methyl. R
^{In 8} or R ⁹ , it is preferably methyl or i-propyl.

The "C1-C6 alkoxy group" includes, for example, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, s-butoxy, t-butoxy, n-pentyloxy, isopentyloxy, 2 -Methylbutoxy, neopentyloxy, 1-ethylpropoxy,
n-hexyloxy, 4-methylpentyloxy, 3-methylpentyloxy, 2-methylpentyloxy, 1-methylpentyloxy, 3,3-dimethylbutoxy, 2,2-dimethylbutoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,3-dimethylbutoxy, 2-
The above “C1-C6 alkyl group” is a group such as ethylbutoxy bonded to an oxygen atom. R ¹ is preferably methoxy. R ² is preferably methoxy, ethoxy, n-propoxy, isopropoxy,
More preferably, it is methoxy. In the substituent of C1~C6 alkyl group R ^2, preferably a methoxy, ethoxy,
n-propoxy and isopropoxy; more preferably methoxy. In the substituent of C1~C6 alkyl group R ^5, preferably methoxy, ethoxy.

The "C1-C6 alkylthio group" includes, for example, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, s-butylthio, t-butylthio, n-pentylthio, isopentylthio, -Methylbutylthio, neopentylthio, 1-ethylpropylthio, n-hexylthio, 4-methylpentylthio, 3-methylpentylthio, 2-methylpentylthio, 1-
Methylpentylthio, 3,3-dimethylbutylthio, 2,2-dimethylbutylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,3-dimethylbutyl Thio, 2-ethylbutylthio, etc.
A "1-C6 alkyl group" is a group bonded to a sulfur atom.
R ² is preferably methylthio, ethylthio, n-propylthio, isopropylthio, and more preferably methylthio. In the substituent of the C1-C6 alkyl group of R ² , it is preferably methylthio. C1~C of R ⁵
In the substituent of the 6 alkyl group, methylthio is preferable.

The "C1-C6 alkylsulfinyl group" includes, for example, methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, isobutylsulfinyl,
s-butylsulfinyl, t-butylsulfinyl, n-pentylsulfinyl, isopentylsulfinyl, 2-methylbutylsulfinyl, neopentylsulfinyl, 1-
Ethylpropylsulfinyl, n-hexylsulfinyl, 4-methylpentylsulfinyl, 3-methylpentylsulfinyl, 2-methylpentylsulfinyl, 1-methylpentylsulfinyl, 3,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 1 Wherein the "C1-C6 alkyl group" such as 1,1-dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl, and 2-ethylbutylsulfinyl is- It is a group bonded to an SO group. In the substituent of C1~C6 alkyl group R ^2, preferably a methylsulfinyl.

The "C1-C6 alkylsulfonyl group" includes, for example, methylsulfonyl, ethylsulfonyl, n-
Propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, s-butylsulfonyl, t-butylsulfonyl, n-pentylsulfonyl, isopentylsulfonyl, 2-methylbutylsulfonyl, neopentylsulfonyl, 1-ethylpropylsulfonyl,
n-hexylsulfonyl, 4-methylpentylsulfonyl,
3-methylpentylsulfonyl, 2-methylpentylsulfonyl, 1-methylpentylsulfonyl, 3,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, It is a group in which the above “C1-C6 alkyl group” is bonded to a —SO ₂ group, such as 1,3-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, and 2-ethylbutylsulfonyl. In the substituent of the C1-C6 alkyl group of R ² , it is preferably methylsulfonyl.

The "C1-C3 alkyl group" is, for example,
Like methyl, ethyl, n-propyl, isopropyl,
It is a linear or branched alkyl group having 1 to 3 carbon atoms.
In the substituent of the amino group of R ² , it is preferably methyl. In R ⁴ , it is preferably methyl. In the substituents of the phenyl moiety of C1~C6 alkyl group in which the phenyl group for R ⁵ is substituted, preferably methyl. R ⁵ of 5
Alternatively, in the substituent of the 5- or 6-membered heterocyclic group of the C1-C6 alkyl group substituted with the 6-membered heterocyclic group, methyl is preferable. In the substituents of C3~C6 cycloalkyl moiety of C1~C6 alkyl group C3~C6 cycloalkyl group is substituted for R ^5, preferably methyl. R
C1-C6 substituted by ⁵ C3-C6 cycloalkenyl groups
The substituent in the C3-C6 cycloalkenyl group of the 6-alkyl group is preferably methyl. C3~C of R ⁵
In the substituent of the 6 cycloalkyl group, it is preferably methyl. In the substituents of C3~C6 cycloalkenyl group R ^5, preferably methyl. In the substituent of the 5- or 6-membered heterocyclic group for R ⁵ , it is preferably methyl. R
^In the substituent of the phenyl group of ⁸ or R ⁹ , it is preferably methyl.

The term "C2-C6 acyl group" refers to a linear or branched C1-C5 alkyl group such as acetyl, propionyl, butyryl, valeryl, n-hexanoyl, isobutyryl, pivaloyl, bonded to carbonyl. Group. R ⁴ is preferably acetyl.
In the substituents of the phenyl moiety of C1~C6 alkyl group in which the phenyl group for R ⁵ is substituted, preferably is acetyl. R ⁵ is preferably acetyl or isobutyryl.

The "C1-C6 alkyl group substituted by 1 to 5 halogen atoms" includes, for example, fluoromethyl, chloromethyl, bromomethyl, difluoromethyl, dichloromethyl, dibromomethyl, trifluoromethyl, 2-fluoro Ethyl, 2-chloroethyl, 2-bromoethyl, 3-fluoropropyl, 3-chloropropyl, 3-bromopropyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl, 5-fluoropentyl, 5-chloropentyl,
5-bromopentyl, 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl, 2,2,2-trifluoroethyl,
2,2,2-trichloroethyl, perfluoroethyl, 3,3,3-
Trifluoropropyl, 4,4,4-trifluorobutyl, 5,
It is a group in which 1 to 5 of the above-mentioned "halogen atoms" are substituted for the above-mentioned "C1-C6 alkyl group", such as 5,5-trifluoropentyl and 6,6,6-trifluorohexyl. R ² is preferably trifluoromethyl, difluoromethyl, or fluoromethyl. In R ⁵ , it is preferably trifluoroethyl.

The "C1-C6 alkoxy group substituted by 1 to 5 halogen atoms" includes, for example, trifluoromethoxy, 2,2,2-trifluoroethoxy, perfluoroethoxy, 2-fluoroethoxy, 3-fluoroethoxy, The above-mentioned “C1-C1” such as fluoropropoxy, 4-fluorobutoxy, 5-fluoropentyloxy, 6-fluorohexyloxy
The “halogen atom” is 1 to 5 in the “C6 alkoxy group”;
This is a substituted group. R ² is preferably trifluoromethoxy.

"C1-C6 alkyl group substituted by one C1-C6 alkoxy group" includes, for example, methoxymethyl, ethoxymethyl, n-propoxymethyl, isopropoxymethyl, n-butoxymethyl, isobutoxymethyl Said "C1-C6 alkyl group", such as s-butoxymethyl, t-butoxymethyl, n-pentyloxymethyl, isopentyloxymethyl, 2-methylbutoxymethyl, neopentyloxymethyl, methoxyethyl, ethoxyethyl Is a group obtained by substituting one of the above “C1 to C6 alkoxy groups”. R ² is preferably methoxymethyl. R ⁵ is preferably methoxymethyl or ethoxymethyl.

The "C1-C6 alkyl group substituted by one C1-C6 alkylthio group" includes, for example, methylthiomethyl, ethylthiomethyl, n-propylthiomethyl, isopropylthiomethyl, n-butylthiomethyl, Such as isobutylthiomethyl, s-butylthiomethyl, t-butylthiomethyl, n-pentylthiomethyl, isopentylthiomethyl, 2-methylbutylthiomethyl, neopentylthiomethyl, methylthioethyl, ethylthioethyl,
It is a group in which one of the above-mentioned "C1-C6 alkylthio group" is substituted for the above-mentioned "C1-C6 alkyl group". In R ² ,
Preferably it is methylthiomethyl. In R ⁵ , it is preferably methylthiomethyl.

The "C1-C6 alkyl group substituted by one C1-C6 alkylsulfinyl group" includes, for example, methylsulfinylmethyl, ethylsulfinylmethyl, n-propylsulfinylmethyl, isopropylsulfinylmethyl, n-butylsulfinyl Such as methyl, isobutylsulfinylmethyl, s-butylsulfinylmethyl, t-butylsulfinylmethyl, n-pentylsulfinylmethyl, isopentylsulfinylmethyl, 2-methylbutylsulfinylmethyl, neopentylsulfinylmethyl, methylsulfinylethyl, ethylsulfinylethyl It is a group in which one of the above-mentioned "C1-C6 alkylsulfinyl group" is substituted for the above-mentioned "C1-C6 alkyl group". R ² is preferably methylsulfinylmethyl.

The "C1-C6 alkyl group substituted by one C1-C6 alkylsulfonyl group" includes, for example, methylsulfonylmethyl, ethylsulfonylmethyl, n-propylsulfonylmethyl, isopropylsulfonylmethyl, n-butylsulfonyl Such as methyl, isobutylsulfonylmethyl, s-butylsulfonylmethyl, t-butylsulfonylmethyl, n-pentylsulfonylmethyl, isopentylsulfonylmethyl, 2-methylbutylsulfonylmethyl, neopentylsulfonylmethyl, methylsulfonylethyl, ethylsulfonylethyl It is a group in which one of the above-mentioned "C1-C6 alkylsulfonyl group" is substituted for the above-mentioned "C1-C6 alkyl group". R ² is preferably methylsulfonylmethyl.

"C1-C1 substituted with one or two hydroxyl groups"
The "C6 alkyl group" is, for example, the above-mentioned "C1-alkyl group" such as 2-hydroxyethyl, 3-hydroxypropyl, 2,3-dihydroxypropyl and 6-hydroxyhexyl
It is a group in which one or two hydroxyl groups are substituted on the “C6 alkyl group”. In R ^5, preferably a 2,3-dihydroxypropyl.

The "C2-C6 alkoxycarbonyl group" is, for example, a straight or branched chain such as methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, n-pentyloxycarbonyl, i-propoxycarbonyl, t-butoxycarbonyl. A C1-C5 alkoxy group is a group bonded to a carbonyl. Of R ⁵ C1~C6
Among the substituents of the alkyl group, methoxycarbonyl and ethoxycarbonyl are preferred. In the substituents of the phenyl moiety of C1~C6 alkyl group in which the phenyl group for R ⁵ is substituted, preferably methoxycarbonyl. R ⁵
Is preferably methoxycarbonyl, ethoxycarbonyl, i-propoxycarbonyl, or t-butoxycarbonyl.

The "C1-C6 alkyl group substituted by one C2-C6 alkoxycarbonyl group" includes, for example,
It is a group in which one of the above-mentioned "C2-C6 alkoxycarbonyl groups" is substituted for the above-mentioned "C1-C6 alkyl groups" such as methoxycarbonylmethyl, ethoxycarbonylmethyl, ethoxycarbonylethyl and ethoxycarbonylpropyl. R ⁵ is preferably methoxycarbonylmethyl or ethoxycarbonylpropyl.

"A C1-C3 alkyl group, a halogen atom,
The "phenyl group substituted by 1 to 5 substituents arbitrarily selected from a C2 to C6 alkoxycarbonyl group and a C2 to C6 acyl group" is, for example, tolyl, xylyl,
Mesityl, fluorophenyl, chlorophenyl, bromophenyl, phenyl iodide, difluorophenyl, dichlorophenyl, chlorofluorophenyl, methoxycarbonylphenyl, ethoxycarbonylphenyl, t-butoxycarbonylphenyl, acetylphenyl, propionylphenyl, pivaloylphenyl, chlorotolyl Such a phenyl group is a group obtained by substituting 1 to 5 substituents arbitrarily selected from the “C1 to C3 alkyl group”, the “halogen atom” and the “C2 to C6 acyl group”. In the substituents of C1~C6 alkyl group R ^5, preferably fluorophenyl, chlorophenyl, methoxycarbonyl phenyl, t- butoxycarbonyl phenyl.

The "phenyl group substituted by 1 to 5 substituents arbitrarily selected from a C1 to C3 alkyl group and a halogen atom" includes, for example, tolyl, xylyl, mesityl, fluorophenyl, chlorophenyl, bromophenyl And phenyl groups such as phenyl iodide, difluorophenyl, dichlorophenyl, chlorofluorophenyl and chlorotolyl are substituted with 1 to 5 substituents arbitrarily selected from the above “C1 to C3 alkyl groups” and the above “halogen atoms”. It is a group that did. R ⁸ or R ⁹ is preferably fluorophenyl or chlorophenyl.

"One phenyl group (the phenyl group is 1
5 to 5 C1-C3 alkyl groups, halogen atoms, C2
C1 to C6 substituted with a C6 alkoxycarbonyl group or a C2 to C6 acyl group)
The term "alkyl group" refers to the above "1 to 6 alkyl groups" such as benzyl, phenethyl, phenylpropyl, phenylhexyl, fluorobenzyl, chlorobenzyl, methoxycarbonylbenzyl, ethoxycarbonylbenzyl, and acetylbenzyl. 5 C
And a phenyl group which may be substituted by a 1-C3 alkyl group, a halogen atom, a C2-C6 alkoxycarbonyl group or a C2-C6 acyl group ".
In R ⁵ , preferably methoxycarbonylbenzyl,
Ethoxycarbonylbenzyl.

The “5- or 6-membered heterocyclic group” is, for example,
Furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, triazolyl, tetrahydrofuranyl,
Tetrahydrothienyl, pyrrolinyl, pyrrolidinyl, pyrazolinyl, pyrazolidinyl, imidazolinyl, imidazolidinyl, 1,3-dioxolanyl, oxazolinyl, isoxazolinyl, pyridyl, pyrimidyl, pyrazyl, pyridazinyl, triazinyl, piperidinyl, piperazinyl, morpholinyl, tetramorphyl , 1,4-dioxanyl. In the substituent of C1~C6 alkyl group R ^5, preferably furyl, triazolyl, tetrahydrofuranyl, oxazolinyl, 1,3-dioxolanyl. R ⁵ is preferably furyl or tetrahydrofuranyl.

The "5- or 6-membered heterocyclic group substituted by 1 to 3 alkyl groups, halogen atoms or oxo groups" includes, for example, methylfuryl, fluorofuryl, chlorothienyl, chloropyridyl, Dimethyl-1,
3-dioxolanyl, dimethyltetrahydrofuranyl,
The above “C1-C3” such as oxotetrahydrofuranyl
An alkyl group, a "halogen atom" or an oxo group is a group obtained by substituting one to three of the above "5- or 6-membered heterocyclic group". In the substituent of C1~C6 alkyl group R ^5,
Preferably it is dimethyl-1,3-dioxolanyl or oxotetrahydrofuranyl. R ⁵ is preferably oxotetrahydrofuranyl.

"One 5- or 6-membered heterocyclic group (the heterocyclic group has 1 to 3 atoms arbitrarily selected from an oxygen atom, a sulfur atom and a nitrogen atom, and has 1 to 3 C1
A C1-C6 alkyl group substituted with a C3 alkyl group, which may be substituted with a halogen atom or an oxo group), includes, for example, furylmethyl, thienylmethyl, triazolylmethyl, 1,3-dioxolanyl The above “1 to C6 alkyl groups” such as methyl, oxazolinylmethyl, dimethyl-1,3-dioxolanylmethyl, tetrahydrofuranylmethyl, furylethyl, furylhexyl, pyridylmethyl and chloropyridylmethyl are referred to as “1 to A three- or five-membered heterocyclic group which may be substituted by three C1-C3 alkyl groups, halogen atoms or oxo groups "is a group substituted by one. In R ⁵ , preferably furylmethyl, oxazolinylmethyl, dimethyl-
1,3-dioxolanylmethyl, triazolylmethyl,
1,3-dioxolanylmethyl and tetrahydrofuranylmethyl.

The "C2-C6 alkenyl group" includes, for example, vinyl, 1-propenyl, 2-propenyl, 1-methyl-2
-Propenyl, 2-methyl-1-propenyl, 2-methyl-2-
Propenyl, 2-ethyl-2-propenyl, 1-butenyl, 2-
Butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-ethyl-2-butenyl, 3-
Butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 1-ethyl-3-butenyl, 1-pentenyl, 2-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-pentenyl, 1-methyl-3-pentenyl, 2-methyl
Carbon number, such as -3-pentenyl, 4-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl 2 to 6 linear or branched alkenyl groups. In R ⁵ , it is preferably 2-propenyl.

The "C2-C6 alkenyl group substituted by 1 to 3 halogen atoms" includes, for example, 1-fluorovinyl, 2-fluorovinyl, 1-chlorovinyl, 2-chlorovinyl, 1-bromovinyl, 2-bromovinyl, 1-fluoro-1-propenyl, 2-fluoro-1-propenyl, 3-fluoro-1-propenyl, 1-chloro-1-propenyl, 2-chloro-1-propenyl, 3-chloro-1- Propenyl, 1-bromo
-1-propenyl, 2-bromo-1-propenyl, 3-bromo-1
-Propenyl, 1-chloro-2-propenyl, 2-chloro-2-
Propenyl, 3-chloro-2-propenyl, 2,3-dichloro-2
-Propenyl, 3,3-dichloro-2-propenyl, 2,3,3-trichloro-2-propenyl, 1,2-dichloro-1-butenyl,
It is a group in which one to three of the above-mentioned "halogen atom" is substituted for the above-mentioned "C2-C6 alkenyl group", such as 1,2-dichloro-1-pentenyl and 1,2-dichloro-1-hexenyl. R ⁵
Is preferably 3-chloro-2-propenyl.

The "C3-C6 cycloalkyl group" is a cyclic alkyl group having 3 to 6 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. In R ⁵ , it is preferably cyclopentyl. In the substituent of C1~C6 alkyl group R ^5, preferably cyclopropyl.

The term "C3-C6 cycloalkyl group substituted by one to three C1-C3 alkyl groups, halogen atoms or oxo groups" means, for example, the above-mentioned "methylcyclopentyl, fluorocyclopropyl, oxocyclopentyl" or the like. "C3-C6 cycloalkyl group"
And a group in which 1 to 3 alkyl groups, 1 to 3 halogen atoms or oxo groups are substituted. Of R ⁵ C1~C6
Among the substituents of the alkyl group, preferred are methylcyclopentyl, chlorocyclopropyl, and oxocyclopentyl. R ⁵ is preferably oxocyclopentyl.

"C1-C6 substituted with one C3-C6 cycloalkyl group (the cycloalkyl group may be substituted with one to three C1-C3 alkyl groups, halogen atoms or oxo groups)""Alkylgroup" means, for example, the above-mentioned "1 to 3 C1-C3 alkyl groups" such as cyclopropylmethyl, cyclopentylmethyl, oxocyclopentylmethyl, chlorocyclopropylbutyl, a halogen atom or "C3-C6 cycloalkyl group optionally substituted by an oxo group" is a group substituted by one. R ⁵ is preferably cyclopentylmethyl or oxocyclopentylmethyl.

"C3-C6 cycloalkenyl group"
For example, C3-C6 such as cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl.
Is a cyclic alkenyl group. In the substituent of C1~C6 alkyl group R ^5, preferably a cyclopentenyl, cyclohexenyl. R ⁵ is preferably cyclopentenyl or cyclohexenyl.

"C3-C6 cycloalkenyl group substituted by one to three C1-C3 alkyl groups, halogen atoms or oxo groups" means, for example, methylcyclopentenyl, fluorocyclopropenyl, oxocyclopentenyl and the like. The “C3 to C6 cycloalkenyl group” includes the “C1 to C3 alkyl group” and the “halogen atom”
Or a group in which 1 to 3 oxo groups are substituted. R ⁵ C
Among the substituents of the 1-C6 alkyl group, preferred are methylcyclopentenyl, chlorocyclopropenyl and oxocyclopentenyl. In R ⁵ , it is preferably oxocyclopentenyl.

"C1-C6 substituted with one C3-C6 cycloalkenyl group (the cycloalkenyl group may be substituted with one to three C1-C3 alkyl groups, halogen atoms or oxo groups) "Alkyl group" means, for example, the above-mentioned "C1 to C6 alkyl group" such as cyclopropenylmethyl, cyclopentenylmethyl, oxocyclopentenylmethyl, and chlorocyclopropylbutenyl; C3- which may be substituted by a halogen atom or an oxo group
"C6 cycloalkenyl group" is a group substituted by one. R
^{In 5} , it is preferably cyclopentenylmethyl, oxocyclopentenylmethyl.

The "C2-C6 alkynyl group" includes, for example, ethynyl, 1-propynyl, 2-propynyl, 1-
C2-C6, such as methyl-2-propynyl, 1-ethyl-2-propynyl, 1-butynyl, 2-butynyl, 1-methyl-2-butynyl, 1-methyl-3-pentynyl, 1-hexynyl Linear or branched alkynyl groups. In R ⁵ , it is preferably 2-propynyl.

The "C2-C6 alkynyl group substituted by 1 to 3 halogen atoms" includes, for example, chloroethynyl, 3-chloro-1-propynyl, 3-chloro-2
-Propynyl, 1-fluoromethyl-2-propynyl,
4,4-difluoro-1-butynyl, 4,4,4-trifluoro-2-butynyl, 4-chloro-1-methyl-2
The aforementioned “C2”, such as -butynyl, 1-trifluoromethyl-3-pentynyl, 6-chloro-1-hexynyl;
To C6 alkynyl group "and 1 to 3 of the above-mentioned" halogen atoms "are substituted. In R ⁵ , preferably 3-
Chloro-2-propynyl.

The "carbamoyl group in which a nitrogen atom may be substituted by a C1-C6 alkyl group" is, for example,
Carbamoyl, methylcarbamoyl, dimethylcarbamoyl, ethylcarbamoyl, diethylcarbamoyl, n
-Propylcarbamoyl, di (n-propyl) carbamoyl, di (i-propyl) carbamoyl, di (n-butyl) carbamoyl, di (n-hexyl) carbamoyl,
And a carbamoyl group such as In R ⁵ , it is preferably dimethylcarbamoyl.

The "cyclic amino group formed by R ⁶ and R ⁷ together with an adjacent nitrogen atom" is, for example, a cyclic amino group such as pyrrolidinyl and piperidinyl. R ⁵
Is preferably piperidinyl.

"C1-C6 alkyl group substituted by one C3-C6 cycloalkyl group" means, for example, cyclopropylmethyl, cyclopentylmethyl and the like.
It is a group in which one of the above-mentioned "C3-C6 cycloalkyl group" is substituted for the above-mentioned "C1-C6 alkyl group". In R ⁵ , it is preferably cyclopropylmethyl.

"Amino group substituted by one or two C1-C3 alkyl groups" means, for example, monomethylamino, monoethylamino, mono-n-propylamino, mono-i-propylamino, In the amino group, "C
A group in which one “1 to C3 alkyl group” is substituted, or an amino group such as dimethylamino, diethylamino, di-n-propylamino, and di-i-propylamino; Is a two-substituted group. R ² is preferably dimethylamino.

The compound (I) of the present invention can be converted into salts such as, for example, sulfates, hydrochlorides, nitrates and phosphates. As long as they can be used as agricultural and horticultural insecticides, they are included in the present invention. Preferably it is a hydrochloride.

The oxime, hydrazone or azine derivative represented by the general formula (I) has two types of stereoisomers, that is, an entgegen form and a tuzamen form. Also includes mixtures in any ratio. In general, the semen body is more suitable than the engegen body because the semen body is superior in insecticidal activity. In addition, both isomers are usually produced in the production process, but generally more semen is produced. Both isomers can be separated by a usual method such as column chromatography.

Incidentally, the determination of the entgegen form and the tubum form was carried out by X-ray crystallography, ¹³ C-NMR and ¹ H-NMR.
Determined by a general structural analysis method.

Hydrates of the compound of the present invention are also included in the present invention.

In the compound represented by the general formula (I) of the present invention, the fused ring group includes tetralin, chroman, chromene, 1,4-benzodioxane, 1,4-
Benzodioxene, 2,3-dihydro-1,4-benzoxazine, 1,4-benzoxathian, preferably tetralin, chroman or 1,4-benzodioxane.

R ^{1 in the} general formula (I) is preferably a halogen atom or a C1-C6 alkyl group.

R ^{2 in the} general formula (I) is preferably a halogen atom, a C1 to C6 alkyl group (the alkyl group is substituted by 1 to 5 halogen atoms or one C1 to C6 alkoxy group). A C1 to C6 alkoxy group (the alkoxy group may be substituted by 1 to 5 halogen atoms), a C1 to C6 alkylthio group, a cyano group or a nitro group, more preferably a halogen atom. It is.

R ^{5 in the} general formula (I) is preferably C 1 -C
6 alkyl groups (the alkyl groups may be substituted by 1 to 5 halogen atoms or 1 C1 to C6 alkoxy group), more preferably unsubstituted C1 to C6
6 alkyl groups.

R ^{4 in the} general formula (I) is preferably a hydrogen atom, a C1-C3 alkyl group or a C2-C3 acyl group, and more preferably a hydrogen atom, a methyl group or an acetyl group.

In the general formula (I), n is preferably 0 or 1.

P in the general formula (I) is preferably 0.

W in the general formula (I) is preferably N.

Next, typical examples of the compound of the present invention represented by the general formula (I) are shown in Table 1 below. In addition, in the column of “condensed ring” in Table 1 below, the group represented by the general formula (I)

[0062]

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The following condensed rings (A) to (G) corresponding to the above are abbreviated by symbols A to G.

[0064]

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In the columns of (R ¹ ) _m and (R ² ) _n , each substituent is shown together with the position of substitution in the condensed ring. In the column of R, the group in the general formula (I)

[0066]

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The groups corresponding to the above are shown together with the substitution positions in the above fused ring. In the column of R, “Imid” indicates a case where W is CH, and “Tliz” indicates a case where W is N. In the following table, "Me" is a methyl group, "Et" is an ethyl group, "i-Pr" is an isopropyl group, "i-Bu" is an isobutyl group, and "t-B
“u” is a tertiary butyl group, “c-Pr” is a cyclopropyl group, “c-Pen” is a cyclopentyl group,
Each is shown. Also, regarding the stereoisomers of the compounds in the table, E is for the endgegen form, Z is for the semen form,
These mixtures are abbreviated as-or only one of EZ, E and Z. The compound numbers will be referred to in the following description.

For example, the compound of Compound No. 78 is represented by the following formula:

[0069]

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The compound represented by

[0071]

[Table 1]

[0072]

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化合物 Compound condensation (R ¹ ) _m (R ² ) _n R Stereo melting point number Ring isomerism (° C) １ 1 A-- 6-C (= NO-i-Pr) Triz Z 64-65 2 A--6-C (= NO-i-Pr) Imid Z Oil 3A--6-C (= NO-Et) Triz Z 4 A - - 6-C ( = NO-i-Bu) Triz Z 5 A - - 6-C (= NO-c-Pen) Triz Z 6 A - - 6-C (= NO-CH 2 CF 3) Triz Z 7 A--6-C (= NO-CH ₂ CH = CH ₂ ) Triz Z 8 A--6-C (= NO-CH ₂ CH = CHCl) Triz Z 9 A--6-C (= _{NO-CH 2 OMe) Triz Z} 10 A - - 6-C (= NO-CH 2 -c-Pr) Triz Z 11 A - 7-Me 6-C (= NO-i-Pr) Triz Z 89-92 12A-7-Et6-C (= NO-i-Pr) Triz Z13A-7-F6-C (= NO-i-Pr) Triz Z14A-7-Cl6-C (= NO -i-Pr) Triz Z 101-103 15 A-7-Br 6-C (= NO-i-Pr) Triz Z 110-111 16 − 7-I 6-C (= NO-i-Pr) Triz Z 17 A − 7-CN 6-C (= NO-i-Pr) Triz Z 18 A − 7-OMe 6-C (= NO-i -Pr) Triz Z 19 A - 7 -OCF 3 6-C (= NO-i-Pr) Triz Z 20 A - 7-CHO 6-C (= NO-i-Pr) Triz Z 21 A - 7-OH 6-C (= NO-i -Pr) Triz Z 22 A - 7-NO 2 6-C (= NO-i-Pr) Triz Z 23 A - 7-NH 2 6-C (= NO-i-Pr ) Triz Z 24 A - 7- NHMe 6-C (= NO-i-Pr) Triz Z 25 A - 7-NMe 2 6-C (= NO-i-Pr) Triz Z 26 A - 7-SMe 6- C (= NO-i-Pr) Triz Z 27 A-7-SOMe 6-C (= NO-i-Pr) Triz Z 28 A-7-SO ₂ Me 6-C (= NO-i-Pr) Triz _{Z 29 A - 7-CHF 2} 6-C (= NO-i-Pr) Triz Z 30 A - 7-CH 2 F 6-C (= NO-i-Pr) Triz Z 31 A - 7-CH 2 OMe 6-C (= NO-i-Pr) Triz Z 32 A-7-CH ₂ SMe 6-C (= NO-i-Pr) Triz Z 33 B--7-C (= NO-i-Pr) Triz Z 63-64 34 B − − 7-C (= NO-Et) Triz Z 35 B − − 7-C (= NO-i-Bu) Triz Z 36 B − − 7-C (= NO-c-Pen ) Triz Z 37 B--7-C (= NO-CH ₂ CF ₃ ) Triz Z 38 B--7-C (= NO-CH ₂ CH = CH ₂ ) Triz Z 39 B − − 7-C (= NO-CH ₂ CH = CHCl) Triz Z 40 B − − 7-C (= NO-CH ₂ OMe) Triz Z 41 B − − 7-C (= NO -CH ₂ -c-Pr) Triz Z 42 B-6-Me 7-C (= NO-i-Pr) Triz Z 43 B-6-Et 7-C (= NO-i-Pr) Triz Z 44 B − 6-F 7-C (= NO-i-Pr) Triz Z 45B − 6-Cl 7-C (= NO-i-Pr) Triz Z 46B − 6-Br 7-C (= NO-i -Pr) Triz Z47B-6-I7-C (= NO-i-Pr) TrizZ48B-6-CN7-C (= NO-i-Pr) TrizZ49B-6-OMe7 -C (= NO-i-Pr ) Triz Z 50 B - 6-OCF 3 7-C (= NO-i-Pr) Triz Z 51 B - 6-CHO 7-C (= NO-i-Pr) Triz Z 52 B - 6-OH 7 -C (= NO-i-Pr) Triz Z 53 B - 6-NO 2 7-C (= NO-i-Pr) Triz Z 54 B - 6-NH 2 7-C (= NO-i-Pr) Triz Z 55 B - 6-NHMe 7-C (= NO-i-Pr) Triz Z 56 B - 6-NMe 2 7-C (= NO-i-Pr) Triz Z 57 B-6-SMe 7-C (= NO-i-Pr) Triz Z 58 B-6-SOMe 7-C (= NO-i-Pr) Triz Z 59 B-6-SO ₂ Me 7-C (= NO-i-Pr) Triz Z 60 B - 6-CHF 2 7-C (= NO-i-Pr) Triz Z 61 B - 6-CH 2 F 7- C (= NO-i-Pr) Triz Z 62 B-6-CH ₂ OMe 7-C (= NO-i-Pr) Triz Z 63 B-6-CH ₂ SMe 7-C (= NO-i-Pr ) Triz Z 64 B 2-t-Bu-7-C (= NO-i-Pr) Triz Z 104-107 65 B 2-t-Bu-7-C (= NO-i-Pr) Imid Z 108- _{110 66 B 2-CH 2 -t} -Bu - 7-C (= NO-i-Pr) Triz EZ oil (1: 9) 67 B 2,2 -Me 2 - 7-C (= NO-i- Pr) Triz Z 98-100 68 B 2,2-Me ₂ -7-C (= NO-i-Pr) Imid Z 100-102 69 B 2,2-Me ₂ -7-C (= NO-i- Pr) Triz E 105-107 70 B 2,2-Me ₂ -7-C (= NO-Et) Triz Z 78-81 71 B 2,2-Me ₂ -7-C (= NO-i-Bu) _{Triz Z 72 B 2,2-Me 2} - 7-C (= NO-c-Pen) Triz Z 73 B 2,2-Me 2 - 7-C (= NO-CH 2 CF 3) Triz Z 74 B 2 _{, 2-Me 2 - 7-} C (= NO-CH 2 CH = CH 2) Triz Z 70-71 75 B 2,2-Me 2 - 7-C (= NO-CH 2 CH = CHCl) Triz Z 76 B 2,2-Me ₂ -7-C (= NO-CH ₂ OMe) Triz Z 77 B 2,2-Me ₂ -7-C (= NO-CH ₂ -c-Pr) Triz Z 78 B 2, _{2-Me 2 6-Me 7} -C (= NO-i-Pr) Triz Z 67-69 79 B 2,2-Me 2 6-Et 7-C (= NO-i-Pr) Triz Z 80 B 2 , 2-Me ₂ 6-F 7-C (= NO-i-Pr) Tr _{iz Z 81 B 2,2-Me 2} 6-Cl 7-C (= NO-i-Pr) Triz Z 80-83 82 B 2,2-Me 2 6-Br 7-C (= NO-i-Pr ) Triz Z 83 B 2,2-Me 2 6-I 7-C (= NO-i-Pr) Triz Z 84 B 2,2-Me 2 6-CN 7-C (= NO-i-Pr) Triz _{Z 85 B 2,2-Me 2 6} -OMe 7-C (= NO-i-Pr) Triz Z 86 B 2,2-Me 2 6-OCF 3 7-C (= NO-i-Pr) Triz Z _{87 B 2,2-Me 2 6-} CHO 7-C (= NO-i-Pr) Triz Z 88 B 2,2-Me 2 6-OH 7-C (= NO-i-Pr) Triz Z 89 B _{2,2-Me 2 6-NO 2} 7-C (= NO-i-Pr) Triz Z 90 B 2,2-Me 2 6-NH 2 7-C (= NO-i-Pr) Triz Z 91 B _{2,2-Me 2 6-NHMe 7} -C (= NO-i-Pr) Triz Z 92 B 2,2-Me 2 6-NMe 2 7-C (= NO-i-Pr) Triz Z 93 B 2 _{, 2-Me 2 6-SMe} 7-C (= NO-i-Pr) Triz Z 94 B 2,2-Me 2 6-SOMe 7-C (= NO-i-Pr) Triz Z 95 B 2,2 _{-Me 2 6-SO 2 Me 7} -C (= NO-i-Pr) Triz Z 96 B 2,2-Me 2 6-CHF 2 7-C (= NO-i-Pr) Triz Z 97 B 2, _{2-Me 2 6-CH 2} F 7-C (= NO-i-Pr) Triz Z 98 B 2,2-Me 2 6-CH 2 OMe 7-C (= NO-i-Pr) Triz Z 99 B 2,2-Me ₂ 6-CH ₂ SMe 7-C (= NO-i-Pr) Triz Z 100 B 2,2-Me ₂ -6-C (= NO-i-Pr) Triz EZ136 -139 (1:19) 101 B-5-Me 6-C (= NO-i-Pr) Triz Z 93-96 102 D--6-C (= NO-i-Pr) Triz Z 74-75 103 D 2,2,3,3-F _4-6 -C (= NO-i-Pr) Triz Z104 D2-OMe-6-C (= NO-i-Pr) Triz Z105 D--6- C (= NO-i-Pr) Imid Z 91-94 106 D-5-Me 6-C (= NO-i-Pr) Triz Z 125-127 107 D-5-Me 6-C (= NO-i -Pr) Imid Z oil 108 D-7-Me 6-C (= NO-i-Pr) Triz Z 126-128 109 D-7-Me 6-C (= NO-i-Pr) Imid Z oil 110 D-7-Me6-C (= NO-i-Pr) Triz E Oil 111 D-7-Me6-C (= NO-Et) Triz Z 112 D-7-Me6-C (= NO -i-Bu) Triz Z 113 D - 7-Me 6-C (= NO-c-Pen) Triz Z 114 D - 7-Me 6-C (= NO-CH 2 CF 3) Triz Z 115 D - 7 -Me 6-C (= NO-CH ₂ CH = CH ₂ ) Triz Z 116 D-7-Me 6-C (= NO-CH ₂ CH = CHCl) Triz Z 117 D-7-Me 6-C (= NO-CH ₂ OMe) Triz Z 118 D-7-Me 6-C (= NO-CH ₂ -c-Pr) Triz Z 119 D-7-Et 6-C (= NO-i-Pr) Triz Z Oil Object 120 D-7-E t 6-C (= NO-i-Pr) Imid Z 121 D-7-F 6-C (= NO-i-Pr) Triz Z 125-128 122 D-7-F 6-C (= NO-i -Pr) Imid Z 87-91 123 D-7-Cl 6-C (= NO-i-Pr) Triz Z 145-147 124 D-7-Cl 6-C (= NO-i-Pr) Imid Z Oil Compound 125 D-7-Br 6-C (= NO-i-Pr) Triz Z 134-137 126 D-7-Br 6-C (= NO-i-Pr) Imid Z Oil 127 D-7-Br 6-C (= NO-i-Pr) Imid E 87-89 128 D-7-I 6-C (= NO-i-Pr) Triz Z 81-84 129 D-7-I 6-C (= NO -i-Pr) Imid Z Oil 130 D-7-I 6-C (= NO-i-Pr) Triz E 68-72 131 D-7-CN 6-C (= NO-i-Pr) Triz Z 155-157 132 D-7-CN 6-C (= NO-i-Pr) Imid Z 133 D-7-OMe 6-C (= NO-i-Pr) Triz Z Oil 134 D-7-OMe 6 -C (= NO-i-Pr ) Imid Z 135 D - 7-OCF 3 6-C (= NO-i-Pr) Triz Z 136 D - 7-OCF 3 6-C (= NO-i-Pr) Imid Z 137 D-7-CHO 6-C (= NO-i-Pr) Triz Z 138 D-7-CHO 6-C (= NO-i-Pr) Imid Z 139 D-7-OH 6-C ( = NO-i-Pr) Triz Z 140 D -7- OH 6-C (= NO- i-Pr) Imid Z 141 D - 7-NO 2 6-C (= NO-i-Pr) Triz Z 153-158 142 D - 7-NO 2 6-C (= NO -i-Pr) Imid Z 143 D - 5-NO 2 6-C (= NO-i-Pr) Triz Z 158-161 144 D - 7-NH 2 6-C (= NO-i-Pr) Triz Z _{145 D - 7-NH 2 6} -C (= NO-i-Pr) Imid Z 146 D - 7-NHMe 6-C (= NO-i-Pr) Triz Z 147 D - 7-NHMe 6-C (= NO-i-Pr) Imid Z 148 D - 7-NMe 2 6-C (= NO-i-Pr) Triz Z oil _{149 D - 7-NMe 2 6} -C (= NO-i-Pr) Imid Z 150 D-7-SMe 6-C (= NO-i-Pr) Triz Z oil 151 D-7-SMe 6-C (= NO-i-Pr) Imid Z 152 D-7-SOMe 6-C ( = NO-i-Pr) Triz Z 153 D-7-SOMe 6-C (= NO-i-Pr) Imid Z 154 D-7-SO ₂ Me 6-C (= NO-i-Pr) Triz Z 155 D-7-SO ₂ Me 6-C (= NO-i-Pr) Imid Z 156 D-7-CHF ₂ 6-C (= NO-i-Pr) Triz Z 124-126 157 D-7-CHF ₂ 6-C (= NO-i-Pr) Imid Z 158 D-7-CH ₂ F 6-C (= NO-i-Pr) Triz Z 159 D-7-CH ₂ F 6-C (= NO-i -Pr) Imid Z 160 D-7-CH ₂ O Me 6-C (= NO-i-Pr) Triz Z 161 D-7-CH ₂ OMe 6-C (= NO-i-Pr) Imid Z 162 D-7-CH ₂ SMe 6-C (= NO- i-Pr) Triz Z 163 D-7-CH ₂ SMe 6-C (= NO-i-Pr) Imid Z 164 F (R ⁴ = Me)--6-C (= NO-i-Pr) Triz Z Oil 165 F (R ⁴ = Me) − − 6-C (= NO-i-Pr) Imid Z Oil 166 F (R ⁴ = Me) − − 6-C (= NO-i-Pr) Triz E Oil 167 F (R ⁴ = Me) − − 6-C (= NO-Et) Triz Z 168 F (R ⁴ = Me) − − 6-C (= NO-i-Bu) Triz Z 169 F (R ⁴ = Me) − − 6-C (= NO-c-Pen) Triz Z 170 F (R ⁴ = Me) − − 6-C (= NO-CH ₂ CF ₃ ) Triz Z 171 F (R ⁴ = Me ) − − 6-C (= NO-CH ₂ CH = CH ₂ ) Triz Z 172 F (R ⁴ = Me) − − 6-C (= NO-CH ₂ CH = CHCl) Triz Z 173 F (R ⁴ = Me) − − 6-C (= NO-CH ₂ OMe) Triz Z 174 F (R ⁴ = Me) − − 6-C (= NO-CH ₂ -c-Pr) Triz Z 175 F (R ⁴ = Me ) − 7-Me 6-C (= NO-i-Pr) Triz Z 176 F (R ⁴ = Me) − 7-Et 6-C (= NO-i-Pr) Triz Z 177 F (R ⁴ = Me ) − 7-F 6-C (= NO-i-Pr) Triz Z178F (R ⁴ = Me) − 7-Cl 6-C (= NO-i-Pr) Triz Z 179 F (R ⁴ = Me) − 7-Br 6-C (= NO-i-Pr) Triz Z 180 F (R ⁴ = Me) − 7-I 6-C (= NO-i-Pr) Triz Z 181F (R ⁴ = Me) − 7-CN 6-C (= NO-i-Pr) Triz Z 182F (R ^{4 = Me) - 7-OMe} 6-C (= NO-i-Pr) Triz Z 183 F (R 4 = Me) - 7-OCF 3 6-C (= NO-i-Pr) Triz Z 184 F ( R ⁴ = Me) − 7-CHO 6-C (= NO-i-Pr) Triz Z185F (R ⁴ = Me) − 7-OH 6-C (= NO-i-Pr) Triz Z186F ( ^{R 4 = Me) - 7-} NO 2 6-C (= NO-i-Pr) Triz Z 187 F (R 4 = Me) - 7-NH 2 6-C (= NO-i-Pr) Triz Z 188 ^{F (R 4 = Me) -} 7-NHMe 6-C (= NO-i-Pr) Triz Z 189 F (R 4 = Me) - 7-NMe 2 6-C (= NO-i-Pr) Triz Z 190 F (R ⁴ = Me) -7-SMe 6-C (= NO-i-Pr) Triz Z 191 F (R ⁴ = Me) -7-SOMe 6-C (= NO-i-Pr) Triz Z ^{192 F (R 4 = Me)} - 7-SO 2 Me 6-C (= NO-i-Pr) Triz Z 193 F (R 4 = Me) - 7-CHF 2 6-C (= NO-i-Pr ) Triz Z 194 F (R ⁴ = Me) − 7-CH ₂ F 6 -C (= NO-i-Pr) Triz Z 195 F (R ⁴ = Me) − 7-CH ₂ OMe 6 -C (= NO -i-Pr) Triz Z 196 F (R ⁴ = Me) − 7-CH ₂ SMe 6-C (= NO-i-Pr) Triz Z 197 F (R ⁴ = Me) − − 7-C (= NO-i-Pr) Triz Z 109 -114 198 F (R ⁴ = Me)--7-C (= NO-Et) Triz Z 199 F (R ⁴ = Me)--7-C (= NO-i-Bu) Triz Z 200 F (R ^{4 = Me) - - 7-} C (= NO-c-Pen) Triz Z 201 F (R 4 = Me) - - 7-C (= NO-CH 2 CF 3) Triz Z 202 F (R 4 = Me ) − − 7-C (= NO-CH ₂ CH = CH ₂ ) Triz Z 203 F (R ⁴ = Me) − − 7-C (= NO-CH ₂ CH = CHCl) Triz Z 204 F (R ⁴ = Me) − − 7-C (= NO-CH ₂ OMe) Triz Z 205 F (R ⁴ = Me) − − 7-C (= NO-CH ₂ -c-Pr) Triz Z 206 F (R ⁴ = Me ) − 6-Me 7-C (= NO-i-Pr) Triz Z 207 F (R ⁴ = Me) − 6-Et 7-C (= NO-i-Pr) Triz Z 208 F (R ⁴ = Me ) − 6-F 7-C (= NO-i-Pr) Triz Z 209 F (R ⁴ = Me) − 6-Cl 7-C (= NO-i-Pr) Triz Z 210 F (R ⁴ = Me ) − 6-Br 7-C (= NO-i-Pr) Triz Z 211F (R ⁴ = Me) − 6-I 7-C (= NO-i-Pr) Triz Z 212 F (R ⁴ = Me ) - 6-CN 7-C (= NO-i-Pr) Triz Z 213 F (R 4 = Me) - 6-OMe 7-C (= NO-i-Pr) Triz Z ^{14 F (R 4 = Me)} - 6-OCF 3 7-C (= NO-i-Pr) Triz Z 215 F (R 4 = Me) - 6-CHO 7-C (= NO-i-Pr) Triz ^{Z 216 F (R 4 = Me} ) - 6-OH 7-C (= NO-i-Pr) Triz Z 217 F (R 4 = Me) - 6-NO 2 7-C (= NO-i-Pr) ^{Triz Z 218 F (R 4 =} Me) - 6-NH 2 7-C (= NO-i-Pr) Triz Z 219 F (R 4 = Me) - 6-NHMe 7-C (= NO-i-Pr ^{) Triz Z 220 F (R 4} = Me) - 6-NMe 2 7-C (= NO-i-Pr) Triz Z 221 F (R 4 = Me) - 6-SMe 7-C (= NO-i- Pr) Triz Z 222 F (R ⁴ = Me) − 6-SOMe 7-C (= NO-i-Pr) Triz Z 223 F (R ⁴ = Me) − 6-SO ₂ Me 7-C (= NO− i-Pr) Triz Z 224 F (R 4 = Me) - 6-CHF 2 7-C (= NO-i-Pr) Triz Z 225 F (R 4 = Me) - 6-CH 2 F 7-C ( = NO-i-Pr) Triz Z 226 F (R ⁴ = Me) − 6-CH ₂ OMe 7-C (= NO-i-Pr) Triz Z 227 F (R ⁴ = Me) − 6-CH ₂ SMe 7-C (= NO-i-Pr) Triz Z228G (p = 0)--6-C (= NO-i-Pr) TrizZ229G (p = 0)--6-C (= NO -Et) Triz Z 230 G (p = 0)--6-C (= NO-i-Bu) Triz Z 231 G (p = 0)--6-C (= NO-c-Pen) Triz Z232 (p = 0) - - 6 -C (= NO-CH 2 CF 3) Triz Z 233 G (p = 0) - - 6-C (= NO-CH 2 CH = CH 2) Triz Z 234 G (p = 0) - - 6-C (= NO-CH 2 CH = CHCl) Triz Z 235 G (p = 0) - - 6-C (= NO-CH 2 OMe) Triz Z 236 G (p = 0) - − 6-C (= NO-CH ₂ -c-Pr) Triz Z 237 G (p = 0) − 7-Me 6-C (= NO-i-Pr) Triz Z 238 G (p = 0) − 7 -Et 6-C (= NO-i-Pr) Triz Z 239 G (p = 0)-7-F 6-C (= NO-i-Pr) Triz Z 240 G (p = 0)-7-Cl 6-C (= NO-i-Pr) Triz Z 241 G (p = 0)-7-Br 6-C (= NO-i-Pr) Triz Z 242 G (p = 0)-7-I 6- C (= NO-i-Pr) Triz Z243G (p = 0) -7-CN6-C (= NO-i-Pr) TrizZ244G (p = 0) -7-OMe6-C ( = NO-i-Pr) Triz Z 245 G (p = 0) - 7-OCF 3 6-C (= NO-i-Pr) Triz Z 246 G (p = 0) - 7-CHO 6-C (= NO-i-Pr) Triz Z 247 G (p = 0) - 7-OH 6-C (= NO-i-Pr) Triz Z 248 G (p = 0) - 7-NO 2 6-C (= NO -i-Pr) Triz Z 249 G (p = 0) - 7-NH 2 6-C (= NO-i-Pr) Triz Z 250 G (p = 0) - 7-NHMe 6-C (= NO- i-Pr) Triz Z 251 G (p = 0) -7 _{-NMe 2 6-C (= NO} -i-Pr) Triz Z 252 G (p = 0) - 7-SMe 6-C (= NO-i-Pr) Triz Z 253 G (p = 0) - 7- SOMe 6-C (= NO-i-Pr) Triz Z 254 G (p = 0) − 7-SO ₂ Me 6-C (= NO-i-Pr) Triz Z 255 G (p = 0) − 7- _{CHF 2 6-C (= NO} -i-Pr) Triz Z 256 G (p = 0) - 7-CH 2 F 6-C (= NO-i-Pr) Triz Z 257 G (p = 0) - 7 -CH ₂ OMe 6-C (= NO-i-Pr) Triz Z258 G (p = 0)-7-CH ₂ SMe 6-C (= NO-i-Pr) Triz Z259 G (p = 1) − − 6-C (= NO-i-Pr) Triz Z 260 G (p = 2) − − 6-C (= NO-i-Pr) Triz Z 261 G (p = 0) − − 7-C ( = NO-i-Pr) Triz Z262G (p = 0)--7-C (= NO-Et) Triz Z263G (p = 0)--7-C (= NO-i-Bu) Triz Z 264 G (p = 0)--7-C (= NO-c-Pen) Triz Z 265 G (p = 0)--7-C (= NO-CH ₂ CF ₃ ) Triz Z 266 G (p = 0) - - 7-C (= NO-CH 2 CH = CH 2) Triz Z 267 G (p = 0) - - 7-C (= NO-CH 2 CH = CHCl) Triz Z 268 G (p = 0) − − 7-C (= NO-CH ₂ OMe) Triz Z 269 G (p = 0) − − 7-C (= NO-CH ₂ -c-Pr) Triz Z 270 G (p = 0) − 6-Me 7-C (= NO-i-Pr) Triz Z 271 G (p = 0) − 6-Et 7-C (= NO-i-Pr) Triz Z 272 G (p = 0) − 6- F 7-C (= NO-i-Pr) Triz Z 273 G (p = 0) -6-Cl 7-C (= NO-i-Pr) Triz Z 274 G (p = 0) -6-Br 7 -C (= NO-i-Pr) Triz Z275G (p = 0) -6-I7-C (= NO-i-Pr) TrizZ276G (p = 0) -6-CN7-C (= NO-i-Pr) Triz Z 277 G (p = 0) - 6-OMe 7-C (= NO-i-Pr) Triz Z 278 G (p = 0) - 6-OCF 3 7-C ( = NO-i-Pr) Triz Z 279 G (p = 0) − 6-CHO 7-C (= NO-i-Pr) Triz Z 280 G (p = 0) − 6-OH 7-C (= NO -i-Pr) Triz Z 281 G (p = 0) - 6-NO 2 7-C (= NO-i-Pr) Triz Z 282 G (p = 0) - 6-NH 2 7-C (= NO -i-Pr) Triz Z 283 G (p = 0) - 6-NHMe 7-C (= NO-i-Pr) Triz Z 284 G (p = 0) - 6-NMe 2 7-C (= NO- i-Pr) Triz Z 286 G (p = 0) - 6-SOMe 7-C (= NO-i-Pr) Triz Z 287 G (p = 0) - 6-SO 2 Me 7-C (= NO- i-Pr) Triz Z 288 G (p = 0) - 6-CHF 2 7-C (= NO-i-Pr) Triz Z 289 G (p = 0) - 6-CH 2 F 7-C (= NO -i-Pr) Triz Z290 G (p = 0) − 6-CH ₂ OMe 7-C (= NO-i-Pr) Triz Z 291 G (p = 0) − 6-CH ₂ SMe 7-C (= NO-i-Pr) Triz Z 292 G (p = 1) − − 7-C (= NO-i-Pr) Triz Z 293 G (p = 2)--7-C (= NO-i-Pr) Triz Z 294 B--5-C (= NO-i-Pr) Triz EZ65-67 (1: 9) 295 B-- 5-C (= NO-i-Pr) Imid Z 296 B--5-C (= NO-Et) Triz Z 297 B--5-C (= NO-i-Bu) Triz 298 B--5- C (= NO-c-Pen) Triz 299 B − − 5-C (= NO-CH ₂ CF ₃ ) Triz Z 300 B − − 5-C (= NO-CH ₂ CH = CH ₂ ) Triz Z 301 B − − 5-C (= NO-CH ₂ CH = CHCl) Triz Z 302 B − − 5-C (= NO-CH ₂ OMe) Triz Z 303 B − − 5-C (= NO-CH ₂ -c- Pr) Triz Z 304 B 2,2-Me ₂ -5-C (= NO-i-Pr) Triz Z 73-75 305 B 2,2-Me ₂ -5-C (= NO-i-Pr) Imid Z oil 306 B 2,2-Me ₂ -5-C (= NO-Et) Triz Z 307 B 2,2-Me ₂ -5-C (= NO-i-Bu) Triz Z 308 B 2,2 _{-Me 2 - 5-C (=} NO-c-Pen) Triz Z 309 B 2,2-Me 2 - 5-C (= NO-CH 2 CF 3) Triz Z 310 B 2,2-Me 2 - 5 -C (= NO-CH ₂ CH = C H ₂ ) Triz Z 311 B 2,2-Me ₂ -5-C (= NO-CH ₂ CH = CHCl) Triz Z 312 B 2,2-Me ₂ -5-C (= NO-CH ₂ OMe) Triz _{Z 313 B 2,2-Me 2 -} 5-C (= NO-CH 2 -c-Pr) Triz Z 314 C 2,2-Me 2 - 6-C (= NO-i-Pr) Triz EZ oil (1:19) 315 C 2,2-Me ₂ -6-C (= NO-i-Pr) Imid Z 316 C 2,2-Me ₂ -6-C (= NO-Et) Triz Z 317 C 2 _{, 2-Me 2 - 6-} C (= NO-i-Bu) Triz Z 318 C 2,2-Me 2 - 6-C (= NO-c-Pen) Triz Z 319 C 2,2-Me 2 - 6-C (= NO-CH ₂ CF ₃ ) Triz Z 320 C 2,2-Me ₂ −6-C (= NO-CH ₂ CH = CH ₂ ) Triz Z 321 C 2,2-Me ₂ −6- C (= NO-CH ₂ CH = CHCl) Triz Z 322 C 2,2-Me ₂ -6-C (= NO-CH ₂ OMe) Triz Z 323 C 2,2-Me ₂ -6-C (= NO _{-CH 2 -c-Pr) Triz Z} 324 C 2,2-Me 2 7-Me 6-C (= NO-i-Pr) Triz Z 325 C 2,2-Me 2 7-Et 6-C (= NO-i-Pr) Triz Z 326 C 2,2-Me 2 7-F 6-C (= NO-i-Pr) Triz Z 327 C 2,2-Me 2 7-Cl 6-C (= NO- i-Pr) Triz Z 328 C 2,2-Me 2 7-Br 6-C (= NO-i-Pr) Triz Z 329 C 2,2-Me 2 7-I 6-C ( = NO-i-Pr) Triz Z 330 C 2,2-Me 2 7-CN 6-C (= NO-i-Pr) Triz Z 331 C 2,2-Me 2 7-OMe 6-C (= NO -i-Pr) Triz Z 332 C 2,2-Me 2 7-OCF 3 6-C (= NO-i-Pr) Triz Z 333 C 2,2-Me 2 7-CHO 6-C (= NO- i-Pr) Triz Z 334 C 2,2-Me 2 7-OH 6-C (= NO-i-Pr) Triz Z 335 C 2,2-Me 2 7-NO 2 6-C (= NO-i -Pr) Triz Z 336 C 2,2- Me 2 7-NH 2 6-C (= NO-i-Pr) Triz Z 337 C 2,2-Me 2 7-NHMe 6-C (= NO-i- Pr) Triz Z 338 C 2,2- Me 2 7-NMe 2 6-C (= NO-i-Pr) Triz Z 339 C 2,2-Me 2 7-SMe 6-C (= NO-i-Pr ) Triz Z 340 C 2,2-Me 2 7-SOMe 6-C (= NO-i-Pr) Triz Z 341 C 2,2-Me 2 7-SO 2 Me 6-C (= NO-i-Pr ) Triz Z 342 C 2,2-Me 2 7-CHF 2 6-C (= NO-i-Pr) Triz Z 343 C 2,2-Me 2 7-CH 2 F 6-C (= NO-i- Pr) Triz Z 344 C 2,2- Me 2 7-CH 2 OMe 6-C (= NO-i-Pr) Triz Z 345 C 2,2-Me 2 7-CH 2 SMe 6-C (= NO- i-Pr) Triz Z 346 E − − 6-C (= NO-i-Pr) Triz Z 64-65 347 E − − 6-C (= NO-i-Pr) Imid Z 97-99 348 E − − 6-C (= NO-Et) Triz Z 349 E − − 6-C (= NO-i-Bu) Triz Z 350 E − − 6-C (= NO-c-Pen) Triz Z 351 E − − 6-C (= NO-CH ₂ CF ₃ ) Triz Z 352 E - - 6- C (= NO-CH 2 CH = CH 2) Triz Z 353 E - - 6-C (= NO-CH 2 CH = CHCl) Triz Z 354 E - - 6-C (= NO-CH ₂ OMe) Triz Z355E − − 6-C (= NO-CH ₂ -c-Pr) Triz Z356E− 7-Me 6-C (= NO-i-Pr) Triz Z357E − 7-Et 6-C (= NO-i-Pr) Triz Z 358 E−7-F 6-C (= NO-i-Pr) Triz Z 359 E− 7-Cl 6-C (= NO-i- Pr) Triz Z 120-121 360 E-7-Br 6-C (= NO-i-Pr) Triz Z 361 E-7-I 6-C (= NO-i-Pr) Triz Z 362 E-7- CN 6-C (= NO- i-Pr) Triz Z 363 E - 7-OMe 6-C (= NO-i-Pr) Triz Z 364 E - 7-OCF 3 6-C (= NO-i-Pr ) Triz Z 365 E - 7- CHO 6-C (= NO-i-Pr) Triz Z 366 E - 7-OH 6-C (= NO-i-Pr) Triz Z 367 E - 7-NO 2 6- C (= NO-i-Pr ) Triz Z 368 E - 7-NH 2 6-C (= NO-i-Pr) Triz Z 369 E - 7-NHMe 6-C (= NO-i-Pr) Triz Z 370 _{E - 7-NMe 2 6-} C (= NO-i-Pr) Triz Z 371 E - 7-SMe 6-C (= NO-i-Pr) Triz Z 372 E - 7-SOMe 6-C (= NO -i-Pr) Triz Z 373 E - 7-SO 2 Me 6-C (= NO-i-Pr) Triz Z 374 E - 7-CHF 2 6-C (= NO-i-Pr) Triz Z 375 E − 7-CH ₂ F 6-C (= NO-i-Pr) Triz Z 376 E − 7-CH ₂ OMe 6-C (= NO-i-Pr) Triz Z 377 E − 7-CH ₂ SMe 6- C (= NO-i-Pr ) Triz Z 378 A 1,1,4,4-Cl 4 - 6-C (= NO-i-Pr) Triz Z 379 A - 5,7-Me 2 6-C ( = NO-i-Pr) Triz Z 380 A-5,7,8-Cl ₃ 6-C (= NO-i-Pr) Triz Z 381 B 4-OMe-7-C (= NO-i-Pr) Triz Z 382 B 4-OMe - 6-C (= NO-i-Pr) Triz Z 383 B - 6,8-Me 2 7-C (= NO-i-Pr) Triz Z 384 B - 5,6, _{8-Br 3 7-C (} = NO-i-Pr) Triz Z 385 C 3,4-Br 2 - 7-C (= NO-i-Pr) Triz Z 386 D - 5,7-Me 2 6- C (= NO-i-Pr) Triz Z 387 D-5,7,8-Cl ₃ 6-C (= NO-i-Pr) Triz Z 388 A--6-C (= NO-i-Pr) Triz E Oil 389 A-7-Me 6-C (= NO-i-Pr) Imid Z Oil 390 A- 8-Me 6-C (= NO-i-Pr) Triz Z 94-95 391 A-8-Me 6-C (= NO-i-Pr) Triz E Oil 392 A-8-Me 6-C ( = NO-i-Pr) Imid Z 76-79 393 A-7-Cl 6-C (= NO-i-Pr) Imid Z 60-65 394 A-7-Br 6-C (= NO-i-Pr ) Triz Z 110-111 395 A-7-Br 6-C (= NO-i-Pr) Triz E oil 396 A-7-Br 6-C (= NO-i-Pr) Imid Z 92-97 397 _{A - 5-NO 2 6-} C (= NO-i-Pr) Triz Z 91-93 398 A 1,1,4,4-Me 4 - 6-C (= NO-i-Pr) Triz Z 110- _{112 399 A 1,1,4,4-Me 4 7} -Me 6-C (= NO-i-Pr) Triz Z 128-131 400 A 1,1,4,4-Me 4 7-Me 6-C (= NO-CH ₂ CH = CH ₂ ) Triz Z oil 401A − −6-C (= N-NMe ₂ ) Triz EZ oil 402 A − −6-C (= N-NMe ₂ ) Imid EZ oil objects 403 A - 7-Me 6- C (= N-NMe 2) Triz EZ oil 404 A - 7-Me 6- C (= N-NMe 2) Imid EZ oil 405 A - 7-Cl 6- C (= N-NMe ₂ ) Triz − 103-104 406 A−7-Cl 6-C (= N-NMe ₂ ) Imid − 73-77 407 A− 7-Br 6-C (= N-NMe ₂ ) Triz −98-100 408 - 7-Br 6-C ( = N-NMe 2) Imid EZ oil _{409 B 2,2-Me 2 - 7} -C (= NO-H) Triz Z 211-212 410 B 2,2-Me 2 - 7-C (= NO-H ) Triz E 183-186 411 B 2,2-Me 2 - 7-C (= NO-Me) Triz Z oil _{412 B 2,2-Me 2 - 7} -C (= NO-CH ₂ SMe) Triz Z oil 413 B 2,2-Me ₂ -7-C (= NO-CH ₂ CO ₂ Me) Triz Z 95-98 414 B 2,2-Me ₂ -7-C ( = NO-CH ₂ CH ₂ CH ₂ Z Oil CO ₂ Et) Triz 415 B 2,2-Me ₂ −7-C (= NO-CH ₂ Ph-4-Z 102-103 CO ₂ Me) Triz 416 B 2,2-Me ₂ −7-C {= NO-CH _2- (1,2,4 Z 140-143 -triazol-1-yl)} Triz 417 B 2,2-Me ₂ −7-C {= NO-CH _2- (1,3 Z oil -dioxolan-2-yl)} Triz 418 B 2,2-Me ₂ -7-C {= NO-CH _2- (furan-2 Z oil -yl) } Triz 419 B 2,2-Me ₂ -7-C {= NO-CH ₂ Z oil-(2,2-dimethyl-1,3-dioxolan-4-yl)} Triz 420 B 2,2-Me _{2 - 7-C {= NO} -CH 2 CH (OH) CH 2 Z oil OH} Triz 421 B 2,2-Me 2 - 7-C {= NO- (2-oxotetra Z 113-117 hydrofuran-3 -yl)} Triz 422 B 2,2-Me ₂ −7-C {= NO- (tetra Z oil hydrofuran-3-yl)} Triz 423 B 2,2-Me 2 - 7-C {= NO- (3-oxocyclo Z 131-135 penten-1-yl)} Triz 424 B 2 _{, 2-Me 2 - 7-} C {= NO-CH 2 - EZ98-100 (oxazolin-2-yl)} Triz (1: 4) 425 B 2,2-Me 2 - 7-C (= NO-COMe ) Triz E 165 426 B 2,2- Me 2 - 7-C (= NO-CONMe 2) Triz Z 137-141 427 B 2,2-Me 2 7-Me 5-C (= NO-i-Pr) Triz Z oil _{428 B 2,2-Me 2 6-} Cl 7-C (= NO-H) Triz Z 160-162 429 B 2,2-Me 2 6-Cl 7-C (= NO-H) Triz EZ188-191 (5: 1) 430 B 2,2-Me 2 6-Cl 7-C (= NO-CH 2 OEt) Triz Z amorphous _{431 B 2,2-Me 2 6-} Cl 7-C (= NO -CH ₂ OEt) Triz EZ oil (13: 4) 432 B 2,2 -Me 2 6-Cl 7-C (= NO-CH 2 C≡CH) Triz Z oil 433 B 2,2-Me ₂ 6-Cl 7-C (= NO-COMe) Triz Z amorphous 434 B 2,2-Me ₂ 6-Cl 7-C (= NO-CO-i-Pr) Triz Z amorphous 435 B 2,2-Me ₂ 6-Cl 7-C (= NO-CO 2 -t-Bu) Triz Z amorphous _{436 B 2,2-Me 2 6-} Cl 7-C (= NO-CONMe 2) Triz Z 141-143 437 _{2,2,3-Me 3 - 7-C} (= NO-i-Pr) Triz Z 83-85 438 B 2,2-Me 2 - 7-C (= N-NMe 2) Triz - 105-107 439 B 2,2-Me ₂ -7-C (= N-NMe ₂ ) Imid-79-80 440 B 2,2-Me ₂ -7-C {(= N- (piperizin--109-111 1-yl )} Triz 441 B 2,2-Me ₂ -7-C {(= N- (piperizin-EZ oil 1-yl)} Triz 442 B 2,2-Me ₂ -7-C (= NN = CH- Ph-4-F) - 117-118 Triz 443 B 2,2-Me 2 - 7-C {= NN = C (Me) -i-Pr} - oil Triz 444 B 2,2-Me ₂ 6- Me 7-C (= N-NMe ₂ ) Triz EZ oil 445 D 2-Me-7-C (= NO-i-Pr) Triz Z oil 446 D 2-Et-7-C (= NO-i -Pr) Triz Z oil 447 D 2-t-Bu-7-C (= NO-i-Pr) Triz Z 66-69 448 D 2-Ph-7-C (= NO-i-Pr) Triz Z _{122-124 449 D 2,2-Me 2 -} 7-C (= NO-i-Pr) Triz Z oil _{450 D 2,3-Me 2 - 7} -C (= NO-i-Pr) Triz Z 61 _{451 D 2,2-Me 2 - 6} -C (= NO-i-Pr) Triz Z oil _{452 D 2,2-Me 2 - 6} -C (= NO-i-Pr) Triz E oil 453 D _{2,2-Me 2 6-Cl 7} -C (= NO-i-Pr) Triz Z oil 454 D - - 6-C ( = N-NMe 2) Triz EZ oil 455 D - 6-Cl 7- C (= N-NMe 2) Triz - 92-95 456 D - 6-Cl 7-C (= N-NMe ₂ ) Imid-oil 457 D-6-I 7-C (= N-NMe ₂ ) Triz-115-118 458 D-6-CN 7-C (= N-NMe ₂ ) Triz EZ oil 459 E - 6-Cl 7- C (= NO-i-Pr) Imid Z oil 460 E - - 6-C ( = N-NMe 2) Triz EZ oil 461 F 3,3-Me ₂ - 6- C (= NO-i-Pr) Triz Z 105-106 (R ⁴ = H) 462 F 3,3-Me ₂ −6-C (= NO-i-Pr) Triz Z Oil (R ⁴ = COMe) _{463 F 3,3-Me 2 - 6} -C (= NO-i-Pr) Triz Z oil ^{(R 4 = Me) 464 A} 2,2-Me 2 - 7-C (= NO-i-Pr) _{Triz Z 465 A 2,2-Me 2} 6-Me 7-C (= NO-i-Pr) Triz Z 466 A 2,2-Me 2 6-Et 7-C (= NO-i-Pr) Triz Z _{467 A 2,2-Me 2 6-} Cl 7-C (= NO-i-Pr) Triz Z 468 A 2,2-Me 2 - 7-C (= N-NMe 2) Triz Z 469 A 2,2 _{-Et 2 - 7-C (=} NO-i-Pr) Triz Z 470 B 2,2-Et 2 - 7-C (= NO-i-Pr) Triz Z 471 B 2,2-Et 2 6-Me 7-C (= NO-i-Pr) Triz Z472 _{B 2,2-Et 2 6-Et} 7-C (= NO-i-Pr) Triz Z 473 B 2,2-Et 2 6-Cl 7-C (= NO-i-Pr) Triz Z 474 B 2 -t-Bu-7-C (= NO-i-Pr) Triz Z 475 B 2-t-Bu 6-Me 7-C (= NO-i-Pr) Triz Z 476 B 2-t-Bu 6- Et 7-C (= NO- i-Pr) Triz Z 477 B 2-t-Bu 6-Cl 7-C (= NO-i-Pr) Triz Z 478 D 2,2-Me 2 6-Me 7- C (= NO-i-Pr ) Triz Z 479 D 2,2-Me 2 6-Et 7-C (= NO-i-Pr) Triz Z 480 D 2,2-Me 2 6-Cl 7-C ( = NO-i-Pr) Triz Z 481 D 2,2-Me 2 6-F 7-C (= NO-i-Pr) Triz Z 482 D 2,2-Me 2 6-CN 7-C (= NO -i-Pr) Triz Z 483 D 2,2-Me 2 6-OMe 7-C (= NO-i-Pr) Triz Z 484 D 2,2-Me 2 6-NO 2 7-C (= NO- i-Pr) Triz Z 485 D 2,2-Me 2 6-CF 3 7-C (= NO-i-Pr) Triz Z 486 D 2,2-Me 2 6-NH 2 7-C (= NO- i-Pr) Triz Z 487 D 2,2-Me 2 6-NMe 2 7-C (= NO-i-Pr) Triz Z 488 D 2,2-Me 2 6-SMe 7-C (= NO-i -Pr) Triz Z 489 D 2,2- Me 2 6-OCH 2 OMe 7-C (= NO-i-Pr) Triz Z 490 D 2-i-Pr - 7-C (= NO-i-Pr) Triz Z 491 D 2-i-Pr 6-Me 7-C (= NO-i-Pr) Triz Z 49 2D 2-i-Pr 6-Cl 7-C (= NO-i-Pr) Triz Z 493 D 2-s-Bu-7-C (= NO-i-Pr) Triz Z 494 D 2-s- Bu 6-Me 7-C (= NO-i-Pr) Triz Z 495 D 2-s-Bu 6-Cl 7-C (= NO-i-Pr) Triz Z 496 D 2-t-Bu 6-Me 7-C (= NO-i-Pr) Triz Z 497 D 2-t-Bu 6-Et 7-C (= NO-i-Pr) Triz Z 498 D 2-t-Bu 6-Cl 7-C ( = NO-i-Pr) Triz Z 499 D 2-t-Bu 6-F 7-C (= NO-i-Pr) Triz Z 500 D 2-t-Bu 6-CN 7-C (= NO-i -Pr) Triz Z 501 D 2- t-Bu 6-OMe 7-C (= NO-i-Pr) Triz Z 502 D 2-t-Bu 6-NO 2 7-C (= NO-i-Pr) Triz Z 503 D 2-t- Bu 6-CF 3 7-C (= NO-i-Pr) Triz Z 504 D 2-t-Bu 6-NH 2 7-C (= NO-i-Pr) Triz Z 505 D 2-t-Bu 6 -NMe 2 7-C (= NO-i-Pr) Triz Z 506 D 2-t-Bu 6-SMe 7-C (= NO-i-Pr) Triz Z 507 D 2 _{-t-Bu 6-OCH 2 OMe} 7-C (= NO-i-Pr) Triz Z 508 D 2,2-Et 2 - 7-C (= NO-i-Pr) Triz Z 509 D 2,2- Et ₂ 6-Me 7-C (= NO-i-Pr) Triz Z 510 D 2,2-Et ₂ 6-Et 7-C (= NO-i-Pr) Triz Z 511 D 2,2-Et ₂ 6-Cl 7-C (= NO-i-Pr) Triz Z 512 D 2,2-Et ₂ 6-F 7-C (= NO-i-Pr) Triz Z 513 D 2,2-Et ₂ 6-CN 7-C (= NO-i-Pr) Triz Z 514 D 2,2-Et ₂ 6- OMe 7-C (= NO-i-Pr) Triz Z 515 D 2-Me-2-Et-7-C (= NO-i-Pr) Triz Z 516 D 2-Me-2-Et 6-Me 7 -C (= NO-i-Pr) Triz Z 517 D 2-Me-2-Et 6-Et 7-C (= NO-i-Pr) Triz Z 518 D 2-Me-2-Et 6-Cl 7 -C (= NO-i-Pr ) Triz Z 519 D 2,2-i-Pr 2 - 7-C (= NO-i-Pr) Triz Z 520 D 2,2-i-Pr 2 6-Me 7 -C (= NO-i-Pr ) Triz Z 521 D 2,2-i-Pr 2 6-Et 7-C (= NO-i-Pr) Triz Z 522 D 2,2-i-Pr 2 6- Cl 7-C (= NO-i-Pr) Triz Z 523 D 2-Me-2-Ph-7-C (= NO-i-Pr) Triz Z 524 D 2-Me-2-Ph 6-Me 7 -C (= NO-i-Pr) Triz Z 525 D 2-Me-2-Ph 6-Et 7-C (= NO-i-Pr) Triz Z 526 D 2-Me-2-Ph 6-Cl 7 -C (= NO-i-Pr) Triz Z 527 D 2,2-Me ₂ -7-C (= N-NMe ₂ ) Triz Z 528 D 2,2-Et ₂ -7-C (= N-NMe _{2) Triz Z 529 D 2-} i-Pr - 7-C (= N-NMe 2) Triz Z 530 D 2-t-Bu - 7-C (= N-NMe 2) Triz Z 531 F 3,3- _{Me 2 7-Me 6-C} (= NO-i-Pr) Triz Z (R 4 = H) 5 _{2 F 3,3-Me 2 7-} Et 6-C (= NO-i-Pr) Triz Z (R 4 = H) 533 F 3,3-Me 2 7-Cl 6-C (= NO-i- ^{Pr) Triz Z (R 4 =} H) 534 F 2,2-Me 2 - 7-C (= NO-i-Pr) Triz Z (R 4 = H) 535 F 2,2-Me 2 6-Me 7 -C (= NO-i-Pr ) Triz Z (R 4 = H) 536 F 2,2-Me 2 6-Et 7-C (= NO-i-Pr) Triz Z (R 4 = H) 537 F _{2,2-Me 2 6-Cl 7} -C (= NO-i-Pr) Triz Z (R 4 = H) 538 D - 7-Br 6-C (= NO-i-Pr) Triz E oil ─中 In the above table, preferred compounds are # 1, # 11, No. 67, 7
No. 0, 78, 81, 108, 121, 123
No. 125, 128, 304, 359, 389
No. 411, 431, 432, 437, 438
Numbers 445, 446, 447, 449, 450
No. 453, and a more preferred compound is 6
7, 78, 81, 108, 123, 125
Nos. 447, 449 and 453.

[0074]

BEST MODE FOR CARRYING OUT THE INVENTION The compound of the present invention can be produced by the following method.

[0075]

Embedded image

In the above formula, R ¹ , R ² , R ³ , R ⁸ , R
⁹ , W, m and n have the same meanings as above, R ^5a has the same meaning as above R ⁵ and is not a hydrogen atom, R ^6a has the same meaning as above R ^6, and R ^7a has the same meaning as above. and R ⁷ the same meaning, and R ^6a and R ^7a are not simultaneously hydrogen atoms, X ¹ is a halogen atom, an alkoxy group, an imidazolyl group,
X ² represents a halogen atom, and Y represents a leaving group such as a halogen atom, a paratoluenesulfonyloxy group or a methanesulfonyloxy group.

(Step A-1) In this step, the carboxylic acid (I
This is a process for producing an acid ester, acid halide or 1-acylimidazole represented by the general formula (III) using I) as a raw material.

This step can be performed by a known method.

(Step A-2) In this step, compound (II)
Reacting I) with a hydroxyamine represented by the general formula R ³ NH ₂ , O-substituted hydroxyamine, hydrazine, N-substituted hydrazine or N, N-disubstituted hydrazine;
This is a step of producing compound (IV).

This step can be performed by a known method. (Step A-3) This step is a step of producing a compound represented by the general formula (V) by halogenating the compound represented by the general formula (IV).

The reaction is carried out in the presence of an inert solvent such as aromatic hydrocarbons such as benzene and toluene, and halogenated hydrocarbons such as chloroform and carbon tetrachloride. React with a halogenating agent such as thionyl chloride, or triphenyl in the presence of an inert solvent such as acetonitrile, nitriles such as propionitrile, aromatic hydrocarbons such as benzene and chlorobenzene. It is carried out by reacting with a halogenating agent comprising phosphine and carbon tetrachloride or carbon tetrabromide. In this case, carbon tetrachloride and carbon tetrabromide can also serve as a solvent.

The reaction temperature ranges from 0 ° C. to the reflux temperature in the reaction system, and is preferably from 50 ° C. to 80 ° C.

The reaction time varies depending on the compound.
~ 6 hours.

(Step A-4) In this step, the carbohydroxymoyl halide compound or carbohydrazonoyl halide compound (V) produced in step A-3 or step B-1 is mixed with imidazole or 1,2,4 A step of reacting -triazole in the presence of a base to produce a carbohydroxymoylazole compound or a carbohydrazonoylazole compound represented by the general formula (VI).

In this step, imidazole or 1,
2,4-Triazole also serves as a base and / or a solvent, and can be used in an equivalent amount or more based on the compound (VI).

Examples of the base to be used include alkali metal hydrides such as sodium hydride and potassium hydride, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, sodium carbonate, and the like. Inorganic bases such as alkali metal carbonates such as potassium carbonate, alkali metal bicarbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate, triethylamine, N, N-dimethylaniline, pyridine, 1,8-diazabicyclo [ And organic bases such as [5.4.0] -7-undecene.

This reaction can be carried out, if necessary, in the presence of a suitable diluent.

Examples of the diluent used include ketones such as acetone and butanone, aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene, and aliphatic hydrocarbons such as petroleum ether and ligroin. , Ethers such as diethyl ether, tetrahydrofuran, dioxane, nitriles such as acetonitrile, propionitrile, amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide And an inert organic solvent such as sulfoxides, and water. Further, a mixed solvent of these can also be used.

The reaction temperature ranges from room temperature to the reflux temperature in the reaction system, preferably from 80 ° C. to 160 ° C.

The reaction time varies depending on the compound.
~ 15 hours.

(Step B-1) In this step, the compound represented by the general formula (VI)
In this step, the aldoxime compound or hydrazone compound represented by I) is reacted with a halogenating agent to produce a carbohydroxymoyl halide compound or carbohydrazonoyl halide compound represented by the general formula (V).

The reaction can be carried out by a known method using N-chlorosuccinimide as a halogenating agent in the presence of N, N-dimethylformamide.

(Step C-1) In this step, a carbohydroxymoylazole compound (VIa) wherein R ³ is a hydroxyl group among the compounds (VI) produced by the above step,
This is a step of reacting a compound represented by the general formula R ^5a Y in the presence of a base to produce a compound of the present invention represented by the general formula (Ia).

In this step, compound R ^5a Y can be used in an amount equal to or more than that of compound (VIa).

Examples of the base to be used include alkali metal hydrides such as sodium hydride and potassium hydride, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, sodium carbonate, and the like. Inorganic bases such as alkali metal carbonates such as potassium carbonate, alkali metal bicarbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate, triethylamine, N, N-dimethylaniline, pyridine, 1,8-diazabicyclo [ And organic bases such as [5.4.0] -7-undecene.

This reaction can be carried out, if necessary, in the presence of a suitable diluent.

Examples of the diluent used include ketones such as acetone and butanone, aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene, and aliphatic hydrocarbons such as petroleum ether and ligroin. , Ethers such as diethyl ether, tetrahydrofuran, dioxane, nitriles such as acetonitrile, propionitrile, amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide And an inert organic solvent such as sulfoxides, and water. Further, a mixed solvent of these can also be used.

The reaction temperature ranges from 0 ° C. to the reflux temperature in the reaction system, and is preferably from 40 ° C. to 100 ° C.

The reaction time varies depending on the compound.
~ 6 hours.

(Step C-2) In this step, a carbohydrazonoylazole compound (VIb) wherein R ³ is an amino group among the compounds (VI) produced by the above step,
This is a step of reacting a compound represented by the general formula R ^6a Y and / or the general formula R ^7a Y in the presence of a base to produce a compound of the present invention represented by the general formula (Ia). In this step, C-1
The reaction can be carried out under the same reaction conditions as in the step.

(Step C-3) In this step, a carbohydrazonoylazole compound (VIb) wherein R ³ is an amino group among the compounds (VI) produced by the above step,
A carbonyl compound represented by the general formula R ⁸ R ⁹ C ＝ O is
This is a step of producing the compound of the present invention represented by the general formula (Ic) by dehydration condensation.

In this step, the compound R ⁸ R ⁹ C ＝ O is
It can be used in an amount equal to or more than that of compound (VI).

This step can be carried out in the presence of an acid or a base.

Examples of the acid used include organic acids such as formic acid, acetic acid, oxalic acid, p-toluenesulfonic acid and trifluoroacetic acid, Lewis acids such as boron trifluoride etherate, hydrochloric acid, sulfuric acid and nitric acid. And the like.

Examples of the base used include hydrides of alkali metals such as sodium hydride and potassium hydride, hydroxides of alkali metals such as sodium hydroxide and potassium hydroxide, sodium carbonate and potassium carbonate. And inorganic salts such as alkali metal bicarbonates such as sodium bicarbonate and potassium bicarbonate, triethylamine, N, N-dimethylaniline, pyridine, 1,8-azadibicyclo [5.
4.0] -7-undecene and the like.

This step can be carried out in the presence of a suitable diluent, if necessary. Examples of the diluent used include aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene, petroleum ethers, aliphatic hydrocarbons such as ligroin, ethers such as diethyl ether, tetrahydrofuran and dioxane. , Acetonitrile, nitriles such as propionitrile, N,
Inactive organic solvents such as amides such as N-dimethylformamide and N-methylpyrrolidone, sulfoxides such as dimethylsulfoxide, and water. Further, a mixed solvent of these can also be used.

The reaction temperature is in the range from 0 ° C. to the reflux temperature in the reaction system, and is preferably from 40 ° C. to 100 ° C.

Various benzoic acids represented by the general formula (II), which are starting materials for producing the compound of the present invention, can be obtained, for example, by the following method.

The 6-tetralincarboxylic acid is a known benzoic acid and can be obtained, for example, by the method described in J. Chem. Soc., 1286 (1938). 6- having a substituent
Tetralincarboxylic acids can also be obtained according to the method.

2,2-Dimethyl-7-chromancarboxylic acid is a bromo group of 2,2-dimethyl-7-bromochroman-2-ene described in J. Med. Chem., 3028 (1990). After lithiation in a metal-halogen exchange reaction, a carboxyl group was introduced by reacting with carbon dioxide,
Subsequently, it can be obtained by performing a catalytic hydrogenation reaction.

2,2-Dimethyl-6-chromancarboxylic acid is a known benzoic acid and is described, for example, in J. Med. Chem.,
1973 (1987).

The 1,4-benzodioxane-6-carboxylic acid can be obtained by oxidizing commercially available 1,4-benzodioxane-6-carboxaldehyde by a known method.

1,4-benzodioxane-7-nitro-
6-carboxylic acid nitrates 1,4-benzodioxane-6-carboxylic acid methyl ester in concentrated nitric acid,
Subsequently, it can be obtained by hydrolyzing the ester.

1,4-benzodioxane-7-methyl-
6-carboxylic acid is, for example, J. Chem. Soc. Perkin Tra
ns. 1,646 (1978).
Benzodioxane is brominated with bromine in acetic acid to give 6
-Bromo-7-methyl-1,4-benzodioxane can be obtained by lithiation of this bromo group by a metal-halogen exchange reaction, followed by reaction with carbon dioxide to introduce a carboxyl group.

1,4-benzodioxane-7-chloro-
6-carboxylic acid, 1,4-benzodioxane-7-bromo-6-carboxylic acid and 1,4-benzodioxane-7
-Iodo-6-carboxylic acid is obtained by reducing 1,4-benzodioxane-7-nitro-6-carboxylic acid methyl ester by a catalytic hydrogenation reaction to obtain 1,4-benzodioxane-7-amino-6. Sandwich carboxylic acid methyl ester
Each of them can be obtained by introducing a halogen atom by a method known as a meyer reaction and then hydrolyzing the ester.

1,4-benzodioxane-7-fluoro-6-carboxylic acid is 1,4-benzodioxane-7-
Amino-6-carboxylic acid methyl ester can be obtained by introducing a fluorine atom by a method known as the Schiemann reaction, followed by hydrolysis of the ester.

2,3-dihydro-4-methyl-1,4-
Benzoxazine-6-carboxylic acid is 3-amino-4
-Methyl hydroxyl benzoate and 1,2-ethylene bromide are reacted in dimethylformamide in the presence of potassium carbonate to obtain methyl 2,3-dihydro-6-benzoxazinecarboxylate, which is converted to methyl by a known method. After the conversion, the ester can be obtained by hydrolyzing the ester.

After completion of each of the above reactions, the target compound of each reaction can be collected from the reaction mixture according to a conventional method.

For example, the reaction mixture is appropriately neutralized, and if insolubles are present, they are removed by filtration. Then, an immiscible organic solvent such as water and ethyl acetate is added.
The organic layer containing the target compound is separated, dried over anhydrous magnesium sulfate or the like, filtered to remove the desiccant, and then evaporated to remove the solvent.

If necessary, the obtained target compound can be obtained by a conventional method.
For example, it can be further purified by recrystallization, reprecipitation or chromatography.

The oxime, hydrazone or azine derivative represented by the general formula (I) of the present invention can be used as an active ingredient of an insecticide. To use the compound of the present invention as an insecticide, the compound of the present invention may be used as it is, but a carrier generally used for formulation, a surfactant,
Mixing dispersing agents or auxiliary agents, powders, wettable powders, emulsions,
It can also be formulated into fine granules or granules and used.

Carriers used in the formulation are as follows:
Examples include solid carriers such as ziglite, talc, bentonite, clay, kaolin, diatomaceous earth, white carbon, vermiculite, slaked lime, silica sand, ammonium sulfate, and urea, and liquid carriers such as isopropyl alcohol, xylene, cyclohexene, and methylnaphthalene. Examples of surfactants and dispersants include metal salts of alkyl benzene sulfonic acid, metal salts of dinaphthyl methane disulfonic acid, alcohol sulfates, alkyl aryl sulfonates, lignin sulfonates, polyoxyethylene alkyl aryl ethers, polyoxyethylene sorbitan Monoalkylates and the like can be mentioned.

For use, they are diluted to an appropriate concentration and sprayed or applied directly.

The insecticide of the present invention can be used for foliage application, soil application,
It can be used by nursery box application or water surface application. The mixing ratio of the active ingredient is appropriately selected according to need, but in the case of a powder or granules, it is preferably 0.1%.
03 to 30% (weight), more preferably 0.05 to 30%.
-20% (weight). When the emulsion or wettable powder is used, the content is preferably 0.5 to 85% (weight), more preferably 1 to 50% (weight).

The application rate of the insecticide of the present invention varies depending on the type of the compound used, the target pest, the tendency of occurrence, the degree of damage, the environmental conditions, the dosage form used, and the like, and is appropriately selected as necessary. When used as such as granules, the amount of the active ingredient is preferably 0.05 g to 5 kg per 10 ares, more preferably 0.1 g to 1 kg per 10 ares. When used in liquid form, such as emulsions and wettable powders, the concentration is preferably 0.1%.
1 to 5000 ppm, more preferably 1 to 100 ppm.
It is 0 ppm.

The insecticide of the present invention comprises other insecticides, fungicides,
Herbicides, fertilizers, and plant growth regulators can be used in combination.

[0127]

EXAMPLES Next, the compounds of the present invention will be specifically described with reference to examples, but the present invention is not limited thereto.

[0128]

Example 1 (Z) -1- (O-isopropyl-6-tetralincar)
(Bihydroxymoyl) -1H-1,2,4-triazoe
Le (1 No. Compound) (1) O-isopropyl-6-tetralin carbo hydrate
Loxamic acid 6-tetralin carboxylic acid 504 mg, thionyl chloride 3
ml was added to 10 ml of benzene, and the mixture was heated under reflux for 100 minutes. The reaction solution was concentrated under reduced pressure to obtain an acid chloride.
O-isopropylhydroxylamine hydrochloride 0.37
g, triethylamine 0.67 g in methylene chloride 10 m
In addition to l, the acid chloride was added thereto. 2 at room temperature
After stirring for an hour, the reaction solution was poured into water and extracted with methylene chloride. The organic layer was washed with water, dried over anhydrous sodium sulfate, filtered, and the solvent was removed under reduced pressure.
g (89% yield).

(2) O-isopropyl-6-tetrali
Emissions carbonitrile hydroximoyl chloride above (1) was prepared by O- isopropyl-6-tetralin-carbonitrile hydroxamic acid 0.59 g, triphenylphosphine 1.00g and carbon tetrachloride 1.17g in acetonitrile 20 ml, and heated to reflux for 30 minutes . The solvent was removed under reduced pressure, and the residue was purified by column chromatography to obtain 0.46 g (yield: 72%) of the target compound.

Nuclear magnetic resonance spectrum ( ¹ H-NMR, 2
00 MHz, CDCl ₃ / TMS) (hereinafter abbreviated as NMR) δ: 1.36 (d, 6H), 1.73-1.88 (m, 4H), 2.73-2.87 (m, 4
H), 4.54 (septet, 1H), 7.06 (d, 1H), 7.53 (s, 1H), 7.55
(d, 1H). (3) (Z) -1- (O-isopropyl-6-tetra)
Lincarbohydroxymoyl) -1H-1,2,4-to
Riazol (No. 1 compound) 200 mg of O-isopropyl-6-tetralincarbohydroxymoyl chloride prepared in (2) above, 1H-
165 mg of 1,2,4-triazole and 330 mg of potassium carbonate were added to 10 ml of N, N-dimethylacetamide and heated at 140 to 160 ° C. for 4 hours. The reaction solution was naturally cooled to room temperature, poured into water, and extracted with a mixed solvent of ethyl acetate and n-hexane. The organic layer is washed with water, dried over anhydrous sodium sulfate, filtered, and the solvent is removed under reduced pressure.
%).

NMR δ: 1.34 (d, 6H), 1.72-1.88 (m, 4H),
2.77 (bs, 4H), 4.54 (septet, 1H), 7.05-7.20 (m, 3H), 8.
04 (s, 1H), 8.91 (s, 1H).

[0132]

Example 2 (Z) -1- (O-isopropyl-2,2-dimethyl-
7-chromancarbohydroxymoyl) -1H-1,
2,4-Triazole (Compound No. 67) 529 mg of O-isopropyl-2,2-dimethyl-7-chromancarbohydroxymoyl chloride produced according to the method of Example 1 (2) above, 1H-1,2,2 645 mg of 4-triazole and 1.3 g of potassium carbonate were added to N,
N-dimethylacetamide 10 ml, 100-1
Heated at 20 ° C. for 10 hours. After the reaction solution was naturally cooled to room temperature, it was poured into water and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate, filtered, the solvent was removed under reduced pressure, and the residue was purified by column chromatography to obtain 408 m of the target product having a melting point of 98 to 100 ° C.
g (yield 69%) was obtained.

NMR δ: 1.32 (d, 6H), 1.33 (s, 6H), 1.81
(t, 2H), 2.79 (t, 2H), 4.45-4.58 (m, 1H), 6.90 (dd, 1H),
6.95 (d, 1H), 7.08 (d, 1H), 8.04 (s, 1H), 8.83 (s, 1H).

[0134]

Example 3 (Z) -1- (O-isopropyl-7-chloro-1,4
-Benzodioxane-6-carbohydroxymoyl)-
Imidazole (Compound No. 124) O-isopropyl-7-chloro-1,4-benzodioxane-6 produced according to the method of Example 1 (2) above.
436 mg of carbohydroxymoyl chloride, 153 mg of imidazole and 623 mg of potassium carbonate were added to N, N-
The mixture was added to 8 ml of dimethylacetamide and heated at 160 ° C. for 5 hours. After the reaction solution was naturally cooled to room temperature, it was poured into water and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate, filtered, the solvent was removed under reduced pressure, and the residue was purified by column chromatography to obtain 404 mg (yield 84%) of the desired product as an oil. .

NMR δ: 1.36 (d, 6H), 4.25-4.35 (m, 4H),
4.50 (septet, 1H), 6.97 (s, 1H), 7.04 (s, 2H), 7.17 (s, 1
H), 8.08 (s, 1H).

[0136]

Example 4 (Z) -1- (O-isopropyl-7-cyano-1,4
-Benzodioxane-6-carbohydroxymoyl)-
1H-1,2,4-triazole (Compound No. 131) (Z) -1 produced according to the method of Example 1 (3) above.
-(O-isopropyl-7-iodo-1,4-benzodioxane-6-carbohydroxymoyl) -1H-1,
174 mg of 2,4-triazole (the 128th compound)
And 90 mg of cuprous cyanide was added to 10 ml of N, N-dimethylformamide and heated at 150 ° C. for 100 minutes. The reaction solution was naturally cooled to room temperature, poured into water, and extracted with a mixed solvent of ethyl acetate and n-hexane. The organic layer is washed with water, dried over anhydrous sodium sulfate, filtered, the solvent is removed under reduced pressure, and the residue is purified by preparative thin-layer chromatography to obtain the desired product 1 having a melting point of 155 to 157 ° C.
00 mg (yield 71%) was obtained.

NMR δ: 1.40 (d, 6H), 4.33 (s, 4H), 4.62
(septet, 1H), 7.03 (s, 1H), 7.25 (s, 1H), 8.01 (s, 1H),
9.15 (s, 1H).

[0138]

Embodiment 5(Z) -1- (O-isopropyl-2,3-dihydro-
4-methyl-1,4-benzoxazine-6-carbothio
Droximoyl) -1H-1,2,4-triazole
 (Compound No. 164) and(E) -1- (O-isopro
Pill-2,3-dihydro-4-methyl-1,4-benzo
Oxazine-6-carbohydroxymoyl) -1H-
1,2,4-triazole(Compound No. 166) O-isoprop produced according to the method of Example 1 (2) above
Ropyl-2,3-dihydro-4-methyl-1,4-ben
Zoxazine-6-carbohydroxymoyl chloride 2
27 mg, 1H-1,2,4-triazole 164 mg
And 220 mg of potassium carbonate in N, N-dimethylacetate
Added to 4 ml of amide and heated at 170 ° C. for 5 hours. reaction
The solution was allowed to cool to room temperature, then poured into water and mixed with ethyl acetate.
The mixture was extracted with a mixed solvent of n-hexane. Wash the organic layer with water
After drying over anhydrous sodium sulfate and filtering, the solvent was reduced.
The residue is purified by preparative thin-layer chromatography.
And the oily Z-form of the desired product (compound # 164)
113 mg (44% yield) of the E-form
6.4 mg of the desired product (No. 166 compound) (yield 2.5
%).

(Z) -1- (O-isopropyl-2,3
-Dihydro-4-methyl-1,4-benzoxazine-
6-carbohydroxymoyl) -1H-1,2,4-triazole (# 164) NMR δ: 1.32 (d, 6H), 2.87 (s, 3H), 3.20-3.30 (m, 2H),
4.24-4.35 (m, 2H), 4.53 (septet, 1H), 6.66-6.82 (m, 3
H), 8.04 (s, 1H), 8.84 (s, 1H). (E) -1- (O-isopropyl-2,3-dihydro-
4-methyl-1,4-benzoxazine-6-carbohydroxymoyl) -1H-1,2,4-triazole (# 166) NMR δ: 1.33 (d, 6H), 2.84 (s, 3H), 3.26-3.31 (m, 2H),
4.31-4.36 (m, 1H), 4.48 (septet, 1H), 6.79 (s, 2H), 6.9
4 (s, 1H), 8.05 (s, 1H), 8.53 (s, 1H). The following compounds were produced according to the above Examples.

(Z) -1- (O-isopropyl-6-te
Toralincarbohydroxymoyl) -imidazole (2
No.) NMR δ: 1.32 (d, 6H), 1.73-1.8.
9 (m, 4H), 2.77 (bd, 4H), 4.4
9 (septet, 1H), 7.03-7.20
(M, 5H), 7.90 (s, 1H). (Z) -1- (O-isopropyl-7-methyl-6-te
Toralincarbohydroxymoyl) -1H-1,2,4
-Triazole (No. 11) NMR δ: 1.38 (d, 6H), 1.75-1.8
2 (m, 4H), 2.00 (s, 3H), 2.71
-2.80 (m, 4H), 4.56 (septet,
1H), 6.94 (s, 1H), 7.07 (s, 1
H), 7.95 (s, 1H), 9.29 (s, 1
H). (Z) -1- (O-isopropyl-7-chloro-6-te
Toralincarbohydroxymoyl) -1H-1,2,4
-Triazole (# 14) NMR δ: 1.35 (d, 6H), 1.70-1.90 (m, 4H), 2.72-2.82
(m, 4H), 4.55 (septet, 1H), 7.08 (d, 1H), 7.34 (d, 1H), 8.
05 (s, 1H), 8.91 (s, 1H). (Z) -1- (O-isopropyl-7-bromo-6-te
Toralincarbohydroxymoyl) -1H-1,2,4
-Triazole (# 15) NMR δ: 1.34 (d, 6H), 1.68-1.90 (m, 4H), 2.70-2.81
(m, 4H), 4.56 (septet, 1H), 7.12 (d, 1H), 7.53 (d, 1H), 8.
05 (s, 1H), 8.91 (s, 1H). (Z) -1- (O-isopropyl-7-chromancarbo)
(Hydroxymoyl) -1H-1,2,4-triazole
(No. 33) NMR δ: 1.33 (d, 6H), 1.95-2.06 (m, 2H), 2.81 (t, 2H),
4.19 (t, 2H), 4.47-4.59 (m, 1H), 6.91-6.97 (m, 2H), 7.0
6 (d, 1H), 8.04 (s, 1H), 8.88 (s, 1H). (Z) -1- (O-isopropyl-2-t-butyl-7
-Chromancarbohydroxymoyl) -1H-1,2,2.
4-triazole (# 64) NMR δ: 1.00 (s, 9H), 1.33 (d, 6H), 1.55-1.75 (m, 1H),
1.95-2.05 (m, 1H), 2.75-2.86 (m, 2H), 3.59 (dd, 1H), 4.
49-4.60 (m, 1H), 6.88 (dd, 1H), 6.94 (d, 1H), 7.05 (d, 1
H), 8.04 (s, 1H), 8.87 (s, 1H). (Z) -1- (O-isopropyl-2-t-butyl-7)
-Chromancarbohydroxymoyl)-imidazole
(# 65) NMR δ: 1.01 (s, 9H), 1.32 (d, 6H), 1.57-1.75 (m, 1H),
1.97-2.10 (m, 1H), 2.70-2.88 (m, 2H), 3.60 (dd, 1H), 4.
40-4.55 (m, 1H), 6.86 (dd, 1H), 6.95 (d, 1H), 7.04 (d, 1
H), 7.11 (s, 1H), 7.17 (s, 1H), 7.89 (s, 1H). (E, Z) -1- ｛O-isopropyl-2- (2,2-
Dimethylpropyl) -7-chromancarbohydroxymo
Ill-1H-1,2,4-triazole (# 66) NMR δ: 1.00 (s, 9H), 1.33 (d, 6H), 1.40 (dd, 1H), 1.7
1 (dd, 1H), 1.75-1.85 (m, 1H), 1.87-2.00 (m, 1H), 2.70-
2.95 (m, 2H), 4.07-4.25 (m, 1H), 4.42-4.60 (m, 1H), 6.89
(d, 1H), 6.92 (s, 1H), 7.05 (d, 1H), 8.03 (s, 1H), 8.55
(s, 1H, (E)), 8.87 (s, 1H, (Z)). (Z) -1- (O-isopropyl-2,2-dimethyl-
7-chromancarbohydroxymoyl) -imidazole
(No. 68) NMR δ: 1.30 (d, 6H), 1.33 (s, 6H), 1.82 (t, 2H), 2.44
(t, 2H), 4.40-4.52 (m, 1H), 6.88 (dd, 1H), 6.94 (d, 1H),
7.07 (d, 1H), 7.10 (s, 1H), 7.15 (s, 1H), 7.88 (s, 1H). (E) -1- (O-isopropyl-2,2-dimethyl-
7-chromancarbohydroxymoyl) -1H-1,
2,4-triazole (# 69) NMR δ: 1.33 (d, 6H), 1.34 (s, 6H), 1.82 (t, 2H), 2.81
(t, 1H), 4.40-4.55 (m, 1H), 6.95 (d, 1H), 6.99 (d, 1H),
7.13 (d, 1H), 8.03 (s, 1H), 8.52 (s, 1H). (Z) -1- (O-ethyl-2,2-dimethyl-7-c
Romancarbohydroxymoyl) -1H-1,2,4-
Triazole (# 70) NMR δ: 1.32 (s, 6H), 1.33 (t, 3H), 1.80 (t, 2H), 2.79
(t, 2H), 4.28 (q, 2H), 6.92 (d, 1H), 6.95 (s, 1H), 7.10
(d, 1H), 8.05 (s, 1H), 8.80 (s, 1H). (Z) -1- (O-allyl-2,2-dimethyl-7-c
Romancarbohydroxymoyl) -1H-1,2,4-
Triazole (# 74) NMR δ: 1.33 (s, 6H), 1.81 (t, 2H), 2.79 (t, 2H), 4.73
(d, 2H), 5.27 (d, 1H), 5.33 (d, 1H), 5.94-6.10 (m, 1H),
6.91 (dd, 1H), 6.93 (d, 1H), 7.08 (dd, 1H), 8.06 (s, 1H),
8.81 (s, 1H). (Z) -1- (O-isopropyl-2,2-dimethyl-
6-methyl-7-chromancarbohydroxymoyl)-
1H-1,2,4-triazole (# 78) NMR δ: 1.32 (s, 6H), 1.37 (d, 6H), 1.79 (t, 2H), 1.97
(s, 3H), 2.76 (t, 2H), 4.55 (septet, 1H), 6.81 (s, 1H),
6.93 (s, 1H), 7.95 (s, 1H), 9.24 (s, 1H). (Z) -1- (O-isopropyl-2,2-dimethyl-
6-chloro-7-chromancarbohydroxymoyl)-
1H-1,2,4-triazole (No. 81) NMR δ: 1.34 (s, 6H), 1.38 (d, 6H), 1.80 (t, 2H), 2.78
(t, 2H), 4.57 (septet, 1H), 7.00 (s, 1H), 7.11 (s, 1H),
7.96 (s, 1H), 9.22 (s, 1H). (E, Z) -1- (O-isopropyl-2,2-dimethyl)
Ru-6-chromancarbohydroxymoyl) -1H-
1,2,4-triazole (# 100) NMR δ: 1.32 (d, 6H), 1.34 (s, 6H), 1.80 (t, 2H), 2.77
(t, 2H), 4.58-4.46 (m, 1H), 6.78 (d, 1H), 7.20 (s, 1H),
7.21 (d, 1H), 8.05 (s, 1H), 8.54 (s, 1H, (E)), 8.85 (s, 1H,
(Z)). (Z) -1- (O-isopropyl-5-methyl-6-k
Romancarbohydroxymoyl) -1H-1,2,4-
Triazole (# 101) NMR δ: 1.38 (d, 6H), 1.98 (s, 3H), 1.98-2.21 (m, 2H),
2.66 (t, 2H), 4.16 (t, 2H), 4.48-4.65 (m, 1H), 6.75 (d, 1
H), 7.10 (d, 1H), 7.93 (s, 1H), 9.39 (s, 1H). (Z) -1- (O-isopropyl-1,4-benzodioxide
Xan-6-carbohydroxymoyl) -1H-1,
2,4-triazole (# 102) NMR δ: 1.32 (d, 6H), 4.22-4.31 (m, 4H), 4.52 (septe
(t, 1H), 6.85-7.07 (m, 3H), 8.05 (s, 1H), 8.86 (s, 1H). (Z) -1- (O-isopropyl-1,4-benzodioxide
Xan-6-carbohydroxymoyl) -imidazole
(# 105) NMR δ: 1.31 (d, 6H), 4.22-4.33 (m, 4H), 4.47 (septe
(t, 1H), 6.84-7.15 (m, 5H), 7.89 (s, 1H). (Z) -1- (O-isopropyl-5-methyl-1,4
-Benzodioxane-6-carbohydroxymoyl)-
1H-1,2,4-triazole (# 106) NMR δ: 1.38 (d, 6H), 1.95 (s, 3H), 4.22-4.32 (m, 4H),
4.56 (septet, 1H), 6.80 (d, 1H), 6.86 (d, 1H), 7.94 (s, 1
H), 9.30 (s, 1H). (Z) -1- (O-isopropyl-5-methyl-1,4
-Benzodioxane-6-carbohydroxymoyl)-
Imidazole (# 107) NMR δ: 1.35 (d, 6H), 1.97 (s, 3H), 4.21-4.34 (m, 4H),
4.48 (septet, 1H), 6.78 (d, 1H), 6.87 (d, 1H), 7.03 (s, 1
H), 7.18 (s, 1H), 8.11 (s, 1H). (Z) -1- (O-isopropyl-7-methyl-1,4
-Benzodioxane-6-carbohydroxymoyl)-
1H-1,2,4-triazole (# 108) NMR δ: 1.37 (d, 6H), 1.98 (s, 3H), 4.22-4.30 (m, 4H),
4.55 (septet, 1H), 6.74 (s, 1H), 6.89 (s, 1H), 7.96 (s, 1
H), 9.24 (s, 1H). (Z) -1- (O-isopropyl-7-methyl-1,4
-Benzodioxane-6-carbohydroxymoyl)-
Imidazole (# 109) NMR δ: 1.35 (d, 6H), 1.98 (s, 3H), 4.21-4.31 (m, 4H),
4.48 (septet, 1H), 6.73 (s, 1H), 6.89 (s, 1H), 7.04 (s, 1
H), 7.17 (s, 1H), 8.08 (s, 1H). (E) -1- (O-isopropyl-7-methyl-1,4
-Benzodioxane-6-carbohydroxymoyl)-
1H-1,2,4-triazole (# 110) NMR δ: 1.28 (d, 6H), 2.07 (s, 3H), 4.22-4.32 (m, 4H),
4.46 (septet, 1H), 6.73 (s, 1H), 6.79 (s, 1H), 8.01 (s, 1
H), 8.53 (s, 1H). (Z) -1- (O-isopropyl-7-ethyl-1,4
-Benzodioxane-6-carbohydroxymoyl)-
1H-1,2,4-triazole (No. 119) NMR δ: 1.10 (t, 3H), 1.38 (d, 6H), 2.32 (q, 2H), 4.23
-4.30 (m, 4H), 4.55 (septet, 1H), 6.80 (s, 1H), 6.85 (s, 1
H), 7.95 (s, 1H), 9.28 (s, 1H). (Z) -1- (O-isopropyl-7-fluoro-1,
4-benzodioxane-6-carbohydroxymoyl)
-1H-1,2,4-triazole (# 121) NMR δ: 1.37 (d, 6H), 4.23-4.32 (m, 4H), 4.56 (septe
t, 1H), 6.65 (d, 1H), 7.05 (d, 1H), 7.97 (s, 1H), 9.14 (s,
1H). (Z) -1- (O-isopropyl-7-fluoro-1,
4-benzodioxane-6-carbohydroxymoyl)
-Imidazole (# 122) NMR δ: 1.34 (d, 6H), 4.23-4.33 (m, 4H), 4.49 (septe
t, 1H), 6.66 (d, 1H), 6.98 (d, 1H), 7.06 (s, 1H), 7.20 (s,
1H), 8.06 (s, 1H). (Z) -1- (O-isopropyl-7-chloro-1,4
-Benzodioxane-6-carbohydroxymoyl)-
1H-1,2,4-triazole (# 123) NMR δ: 1.39 (d, 6H), 4.28 (s, 4H), 4.57 (septet, 1H),
6.95 (s, 1H), 7.07 (s, 1H), 7.96 (s, 1H), 9.22 (s, 1H). (Z) -1- (O-isopropyl-7-bromo-1,4
-Benzodioxane-6-carbohydroxymoyl)-
1H-1,2,4-triazole (# 125) NMR δ: 1.39 (d, 6H), 4.28 (s, 4
H), 4.58 (septet, 1H), 7.08
(S, 1H), 7.12 (s, 1H), 7.96
(S, 1H), 9.24 (s, 1H). (Z) -1- (O-isopropyl-7-bromo-1,4
-Benzodioxane-6-carbohydroxymoyl)-
Imidazole (# 126) NMR δ: 1.36 (d, 6H), 4.25-4.3
5 (m, 4H), 4.50 (septet, 1H),
7.03-7.18 (m, 4H), 8.09 (s, 1
H). (E) -1- (O-isopropyl-7-bromo-1,4
-Benzodioxane-6-carbohydroxymoyl)-
Imidazole (No. 127) NMR δ: 1.30 (d, 6H), 4.29 (s, 4H), 4.48 (septet, 1H),
6.84-7.17 (m, 4H), 7.90 (bs, 1H). (Z) -1- (O-isopropyl-7-iodo-1,4)
-Benzodioxane-6-carbohydroxymoyl)-
1H-1,2,4-triazole (# 128) NMR δ: 1.40 (d, 6H), 4.27 (s, 4H), 4.59 (septet, 1H),
7.04 (s, 1H), 7.36 (s, 1H), 7.97 (s, 1H), 9.28 (s, 1H). (Z) -1- (O-isopropyl-7-iodo-1,4
-Benzodioxane-6-carbohydroxymoyl)-
Imidazole (No. 129) NMR δ: 1.37 (d, 6H), 4.26-4.33 (m, 4H), 4.51 (septe
(t, 1H), 7.05-7.18 (m, 3H), 7.37 (s, 1H), 8.11 (s, 1H). (E) -1- (O-isopropyl-7-iodo-1,4)
-Benzodioxane-6-carbohydroxymoyl)-
1H-1,2,4-triazole (# 130) NMR δ: 1.33 (d, 6H), 4.28 (s, 4H), 4.53 (septet, 1H),
6.86-7.04 (m, 2H), 8.05 (s, 1H), 8.86 (s, 1H). (Z) -1- (O-isopropyl-7-methoxy-1,
4-benzodioxane-6-carbohydroxymoyl)
-1H-1,2,4-triazole (# 133) NMR δ: 1.36 (d, 6H), 3.53 (s, 3H), 4.20-4.31 (m, 4H),
4.54 (septet, 1H), 6.45 (s, 1H), 7.06 (s, 1H), 7.91 (s, 1
H), 9.12 (s, 1H). (Z) -1- (O-isopropyl-7-nitro-1,4
-Benzodioxane-6-carbohydroxymoyl)-
1H-1,2,4-triazole (# 141) NMR δ: 1.41 (d, 6H), 4.38 (s, 4H), 4.58 (septet, 1H),
7.14 (s, 1H), 7.82 (s, 1H), 7.84 (s, 1H), 9.38 (s, 1H). (Z) -1- (O-isopropyl-5-nitro-1,4
-Benzodioxane-6-carbohydroxymoyl)-
1H-1,2,4-triazole (# 143) NMR δ: 1.35 (d, 6H), 4.39 (s, 4H), 4.54 (septet, 1H),
6.98 (d, 1H), 7.07 (d, 1H), 7.95 (s, 1H), 9.16 (s, 1H). (Z) -1- (O-isopropyl-7-dimethylamino
-1,4-benzodioxane-6-carbohydroxymo
Yl) -1H-1,2,4-triazole (# 148) NMR δ: 1.36 (d, 6H), 2.44 (s, 6H), 4.20-4.32 (m, 4H),
4.55 (septet, 1H), 6.62 (s, 1H), 7.03 (s, 1H), 7.89 (s, 1
H), 9.09 (s, 1H). (Z) -1- (O-isopropyl-7-methylthio-
1,4-benzodioxane-6-carbohydroxymoy
Le) -1H-1,2,4-triazole (# 150) NMR δ: 1.38 (d, 6H), 2.30 (s, 3H), 4.24-4.33 (m, 4H),
4.57 (septet, 1H), 6.93 (s, 1H), 6.97 (s, 1H), 7.95 (s, 1
H), 9.23 (s, 1H). (Z) -1- (O-isopropyl-7-difluoromethyl)
1,4-benzodioxane-6-carbohydroxy
Moyl) -1H-1,2,4-triazole (156
No.) NMR δ: 1.38 (d, 6H), 4.27-4.33 (m, 4H), 4.56 (septe
t, 1H), 6.58 (t, 1H), 6.88 (s, 1H), 7.24 (s, 1H), 7.97 (s,
1H), 9.21 (s, 1H). (Z) -1- (O-isopropyl-2,3-dihydro-
4-methyl-1,4-benzoxazine-6-carbothio
Droximoyl) -imidazole (# 165) NMR δ: 1.32 (d, 6H), 2.86 (s, 3H), 3.25-3.32 (m, 2H),
4.29-4.38 (m, 2H), 4.48 (septet, 1H), 6.68-6.80 (m, 3
H), 7.10 (s, 1H), 7.17 (s, 1H), 7.91 (s, 1H). (Z) -1- (O-isopropyl-2,3-dihydro-
4-methyl-1,4-benzoxazine-7-carbohi
Droximoyl) -1H-1,2,4-triazole
(# 197) NMR δ: 1.30 (d, 6H), 2.93 (s, 3H), 3.33 (t, 2H), 4.27
(t, 2H), 4.50 (septet, 1H), 6.58-6.97 (m, 3H), 8.05 (s, 1
H), 8.78 (s, 1H). (E, Z) -1- (O-isopropyl-5-chromanka)
Rubohydroxymoyl) -1H-1,2,4-triazo
(No. 294) NMR δ: 1.37 (d, 6H), 1.85-2.02 (m, 2H), 2.44 (t, 2H),
4.15 (t, 2H), 4.47-4.63 (m, 1H), 6.91 (d, 1H), 6.92 (d, 1
H), 7.16 (t, 1H), 7.95 (s, 1H), 8.52 (s, 1H, (E)), 9.26 (s,
1H, (Z)). (Z) -1- (O-isopropyl-2,2-dimethyl-
5-chromancarbohydroxymoyl) -1H-1,
2,4-triazole (# 304) NMR δ: 1.31 (s, 6H), 1.38 (d, 6H), 1.71 (t, 2H), 2.39
(t, 2H), 4.50-4.62 (m, 1H), 6.92 (d, 2H), 7.18 (t, 1H),
7.94 (s, 1H), 9.26 (s, 1H). (Z) -1- (O-isopropyl-2,2-dimethyl-
5-chromancarbohydroxymoyl) -imidazole
(# 305) NMR δ: 1.30 (s, 6H), 1.36 (d, 6H), 1.71 (t, 2H), 2.40
(t, 2H), 4.40-4.60 (m, 1H), 6.92 (d, 1H), 6.94 (d, 1H),
7.04 (s, 1H), 7.13 (s, 1H), 7.17 (t, 1H), 8.13 (s, 1H). (E, Z) -1- (O-isopropyl-2,2-dimethyl)
-2H-chromen-6-carbohydroxymoyl)-
1H-1,2,4-triazole (# 314) NMR δ: 1.32 (d, 6H), 1.44 (s, 6H), 4.40-4.60 (m, 1H),
5.64 (d, 1H), 6.29 (d, 1H), 6.78 (d, 1H), 7.13 (d, 1H),
7.23 (d, 1H), 8.06 (s, 1H), 8.54 (s, 1H, (E)), 8.84 (s, 1H,
(Z)). (Z) -1- (O-isopropyl-1,4-benzooxy)
Sedin-6-carbohydroxymoyl) -1H-1,
2,4-triazole (No. 346) NMR δ: 1.32 (d, 6H), 4.52 (septet, 1H), 5.88 (s, 2H),
6.62 (d, 1H), 6.81 (d, 1H), 6.94 (dd, 1H), 8.05 (s, 1H),
8.84 (s, 1H). (Z) -1- (O-isopropyl-1,4-benzooxy)
Sedin-6-carbohydroxymoyl) -imidazole
(No. 347) NMR δ: 1.30 (d, 6H), 4.47 (septet, 1H), 5.89 (s, 2H),
6.61 (d, 1H), 6.80 (d, 1H), 6.87 (dd, 1H), 7.11-7.13 (m,
2H), 7.87 (s, 1H). (Z) -1- (O-isopropyl-7-chloro-1,4
-Benzoxedin-6-carbohydroxymoyl)-
1H-1,2,4-triazole (# 359) NMR δ: 1.38 (d, 6H), 4.56 (sep)
tet, 1H), 5.88 (s, 2H), 6.69
(S, 1H), 6.80 (s, 1H), 7.96
(S, 1H), 9.19 (s, 1H). (E) -1- (O-isopropyl-6-tetralincal
(Bihydroxymoyl) -1H-1,2,4-triazoe
(No. 388) NMR δ: 1.32 (d, 6H), 1.75-1.9
0 (m, 4H), 2.75-2.85 (m, 4H),
4.47 (septet, 1H), 7.12-7.3
1 (m, 3H), 8.04 (s, 1H), 8.57
(S, 1H). (Z) -1- (O-isopropyl-7-methyl-6-te
Toralincarbohydroxymoyl) -imidazole (3
No. 89) NMR δ: 1.35 (d, 6H), 1.75-1.85 (m, 4H), 2.02 (s, 3H),
2.68-2.80 (m, 4H), 4.48 (septet, 1H), 6.93 (s, 1H), 7.0
3-7.05 (m, 2H), 7.18 (s, 1H), 8.10 (s, 1H). (Z) -1- (O-isopropyl-8-methyl-6-te
Toralincarbohydroxymoyl) -1H-1,2,4
-Triazole (# 390) NMR δ: 1.34 (d, 6H), 1.68-1.90 (m, 4H), 2.21 (s, 3H),
2.58-2.67 (m, 2H), 2.72-2.80 (m, 2H), 4.54 (septet, 1
H), 7.02 (s, 1H), 7.06 (s, 1H), 8.03 (s, 1H), 8.91 (s, 1
H). (E) -1- (O-Isopropyl-8-methyl-6-te
Toralincarbohydroxymoyl) -1H-1,2,4
-Triazole (# 391) NMR δ: 1.33 (d, 6H), 1.70-1.92 (m, 4H), 2.21 (s, 3H),
2.59-2.68 (m, 2H), 2.72-2.80 (m, 2H), 4.47 (septet, 1
H), 7.09 (s, 2H), 8.03 (s, 1H), 8.56 (s, 1H). (Z) -1- (O-isopropyl-8-methyl-6-te
Toralincarbohydroxymoyl) -imidazole (3
No. 92) NMR δ: 1.32 (d, 6H), 1.70-1.91 (m, 4H), 2.21 (s, 3H),
2.59-2.68 (m, 2H), 2.71-2.80 (m, 2H), 4.49 (septet, 1
H), 7.00 (s, 1H), 7.08 (s, 1H), 7.10-7.12 (m, 1H), 7.17-
7.18 (m, 1H), 7.90 (s, 1H). (Z) -1- (O-isopropyl-7-chloro-6-te)
Toralincarbohydroxymoyl) -imidazole (3
No. 93) NMR δ: 1.32 (d, 6H), 1.70-1.91 (m, 4H), 2.70-2.82
(m, 4H), 4.50 (septet, 1H), 7.04 (d, 1H), 7.13 (s, 2H), 7.
33 (d, 1H), 7.89 (s, 1H). (Z) -1- (O-isopropyl-7-bromo-6-te
Toralincarbohydroxymoyl) -1H-1,2,4
-Triazole (# 394) NMR δ: 1.34 (d, 6H), 1.68-1.90 (m, 4H), 2.70-2.81
(m, 4H), 4.56 (septet, 1H), 7.12 (d, 1H), 7.53 (d, 1H), 8.
05 (s, 1H), 8.91 (s, 1H). (E) -1- (O-isopropyl-7-bromo-6-te
Toralincarbohydroxymoyl) -1H-1,2,4
-Triazole (# 395) NMR δ: 1.33 (d, 6H), 1.70-1.91 (m, 4H), 2.71-2.81
(m, 4H), 4.47 (septet, 1H), 7.13 (d, 1H), 7.59 (d, 1H), 8.
04 (s, 1H), 8.59 (s, 1H). (Z) -1- (O-isopropyl-7-bromo-6-te
Toralincarbohydroxymoyl) -imidazole (3
No. 96) NMR δ: 1.32 (d, 6H), 1.70-1.90 (m, 4H), 2.71-2.80
(m, 4H), 4.50 (septet, 1H), 7.08 (d, 1H), 7.13 (s, 2H), 7.
52 (d, 1H), 7.89 (s, 1H). (Z) -1- (O-isopropyl-5-nitro-6-te
Toralincarbohydroxymoyl) -1H-1,2,4
-Triazole (# 397) NMR δ: 1.35 (d, 6H), 1.77-1.88 (m, 4H), 2.72-2.82
(m, 2H), 2.82-2.92 (m, 2H), 4.54 (septet, 1H), 7.20-7.3
3 (m, 2H), 7.95 (s, 1H), 9.20 (s, 1H). (Z) -1- (O-isopropyl-1,1,4,4-te
Tramethyl-6-tetralincarbohydroxymoyl)
-1H-1,2,4-triazole (# 398) NMR δ: 1.26 (s, 6H), 1.28 (s, 6H), 1.33 (d, 6H), 1.69
(s, 4H), 4.55 (quintet, 1H), 7.17 (dd, 1H), 7.24 (d, 1H),
7.35 (d, 1H), 8.06 (s, 1H), 8.90 (s, 1H). (Z) -1- (O-isopropyl-1,1,4,4,7
-Pentamethyl-6-tetralincarbohydroxymoi
M) -1H-1,2,4-triazole (# 399) NMR δ: 1.25 (s, 6H), 1.28 (s, 6H), 1.40 (d, 6H), 1.67
(s, 4H), 2.07 (s, 3H), 4.55 (quintet, 1H), 7.15 (s, 1H),
7.22 (s, 1H), 7.97 (s, 1H), 9.26 (s, 1H). (Z) -1- (O-allyl-1,1,4,4,7-pen
Tamethyl-6-tetralincarbohydroxymoyl)-
1H-1,2,4-triazole (# 400) NMR δ: 1.25 (s, 6H), 1.27 (s, 6H), 1.67 (s, 4H), 2.04
(s, 3H), 4.79 (d, 2H), 5.29-5.42 (m, 2H), 6.04-6.15 (m, 1
H), 7.14 (s, 1H), 7.24 (s, 1H), 8.43 (s, 1H), 9.22 (s, 1
H). (E, Z) -1- (N, N-dimethyl-6-tetralin
(Carbohydrazonoyl) -1H-1,2,4-triazo
(# 401) NMR δ: 1.73-1.85 (m, 4H), 2.59 (s, 3.6H), 2.63 (s, 2.
4H), 2.66-2.85 (m, 4H), 7.10 (s, 1.8H), 7.10-7.20 (m, 1.2
H), 7.96 (s, 0.4H), 8.15 (s, 0.6H), 8.50 (s, 0.6H), 8.
55 (s, 0.4H). (E, Z) -1- (N, N-dimethyl-6-tetralin
Carbohydrazonoyl) -imidazole (# 402) NMR δ: 1.72-1.88 (m, 4H), 2.50 (s, 1.2H), 2.52 (s, 4.
8H), 2.68-2.85 (m, 4H), 6.99-7.20 (m, 5H), 7.66 (s, 0.2
H), 7.75 (s, 0.8H). (E, Z) -1- (N, N-dimethyl-7-methyl-6
-Tetralincarbohydrazonoyl) -1H-1,2,2.
4-Triazole (# 403) NMR δ: 1.73-1.85 (m, 4H), 1.95 (s, 0.6H), 2.08 (s, 2.
4H), 2.59 (s, 1.2H), 2.62 (s, 4.8H), 2.69-2.80 (m, 4H),
6.89 (s, 0.2H), 6.98 (s, 1.8H), 7.93 (s, 0.8H), 8.00 (s,
0.2E), 8.53 (s, 0.8H), 9.16 (s, 0.2H). (E, Z) -1- (N, N-dimethyl-7-methyl-6)
-Tetralincarbohydrazonoyl) -imidazole
(# 404) NMR δ: 1.72-1.88 (m, 4H), 1.96 (s, 2.1H), 2.10 (s, 0.
9H), 2.50 (s, 1.8H), 2.55 (s, 4.2H), 2.67-2.80 (m, 4H),
6.88 (s, 0.7H), 6.94 (s, 0.3H), 6.98 (s, 1H), 7.03-7.04
(m, 0.3H), 7.07-7.08 (m, 0.7H), 7.28-7.29 (m, 0.3H), 7.
41-7.42 (m, 0.7H), 7.54 (s, 0.3H), 7.95 (s, 0.7H). 1- (N, N-dimethyl-7-chloro-6-tetralin
(Carbohydrazonoyl) -1H-1,2,4-triazo
(# 405) NMR δ: 1.63-1.88 (m, 4H), 2.64 (s, 6H), 2.58-2.77
(m, 4H), 6.78 (d, 1H), 7.19 (d, 1H), 8.17 (s, 1H), 8.43
(s, 1H). 1- (N, N-dimethyl-7-chloro-6-tetralin
Carbohydrazonoyl) -imidazole (# 406) NMR δ: 1.64-1.90 (m, 4H), 2.56 (s, 6H), 2.65-2.83
(m, 4H), 6.90 (s, 1H), 7.12-7.13 (m, 1H), 7.21 (s, 1H),
7.25-7.26 (m, 1H), 7.70 (s, 1H). 1- (N, N-dimethyl-7-bromo-6-tetralin
(Carbohydrazonoyl) -1H-1,2,4-triazo
(# 407) NMR δ: 1.64-1.90 (m, 4H), 2.64 (s, 6H), 2.60-2.80
(m, 4H), 6.80 (d, 1H), 7.39 (d, 1H), 8.17 (s, 1H), 8.42
(E, Z) -1- (N, N-dimethyl-7-bromo-6)
-Tetralincarbohydrazonoyl) -imidazole
(# 408) NMR δ: 1.65-1.90 (m, 4H), 2.52 (s, 1.5H), 2.56 (s, 4.
5H), 2.66-2.82 (m, 4H), 6.92-6.93 (s, 0.7H), 7.04-7.06
(s, 0.3H), 7.12-7.15 (m, 1H), 7.21-7.22 (m, 0.7H), 7.22
-7.25 (m, 0.3H), 7.45-7.47 (m, 0.7H), 7.51-7.53 (m, 0.3
H), 7.66-7.68 (m, 0.3H), 7.70-7.71 (m, 0.7H). (Z) -1- (2,2-dimethyl-7-chromancarbo)
(Hydroxymoyl) -1H-1,2,4-triazole
(# 409) NMR δ: 1.33 (s, 6H), 1.81 (t, 2H), 2.80 (t, 2H), 6.91
(dd, 1H), 7.00 (d, 1H), 7.18 (d, 1H), 8.12 (s, 1H), 8.86
(s, 1H), 9.51 (s, 1H). (E) -1- (2,2-dimethyl-7-chromancarbo)
(Hydroxymoyl) -1H-1,2,4-triazole
(# 410) NMR δ: 1.35 (s, 3H), 1.59 (s, 3H), 1.83 (t, 2H), 2.83
(t, 2H), 6.93-7.21 (m, 3H), 8.01-8.08 (m, 2H), 8.52 (s, 1
H). (Z) -1- (O-methyl-2,2-dimethyl-7-k)
Romancarbohydroxymoyl) -1H-1,2,4-
Triazole (# 411) NMR δ: 1.31 (s, 6H), 1.80 (t, 2H), 2.78 (t, 2H), 4.03
(s, 3H), 6.91 (s, 1H), 6.92 (d, 1H), 7.07 (d, 1H), 8.05
(s, 1H), 8.75 (s, 1H). (Z) -1- (O-methylthiomethyl-2,2-dimethyl)
Ru-7-chromancarbohydroxymoyl) -1H-
1,2,4-triazole (# 412) NMR δ: 1.32 (s, 6H), 1.81 (t, 2H), 2.27 (s, 3H), 2.80
(t, 2H), 5.29 (s, 2H), 6.92 (d, 1H), 6.94 (s, 1H), 7.08
(d, 1H), 8.07 (s, 1H), 8.79 (s, 1H). (Z) -1- (O-methoxycarbonylmethyl-2,2
-Dimethyl-7-chromancarbohydroxymoyl)-
1H-1,2,4-triazole (# 413) NMR δ: 1.29 (s, 6H), 1.80 (t, 2H), 2.79 (t, 2H), 3.80
(s, 3H), 4.78 (s, 2H), 6.90 (dd, 1H), 6.92 (d, 1H), 7.09
(d, 1H), 8.07 (s, 1H), 9.05 (s, 1H). (Z) -1- ｛O- (3-ethoxycarbonylpropyl
) -2,2-dimethyl-7-chromancarbohydroxy
Shimoyl｝ -1H-1,2,4-triazole (414
No.) NMR δ: 1.25 (t, 3H), 1.33 (s, 6H), 1.81 (t, 2H), 2.07
(quintet, 2H), 2.38 (t, 2H), 2.79 (t, 2H), 4.12 (q, 2H),
4.28 (t, 2H), 6.85-6.95 (m, 2H), 7.08 (d, 1H), 8.06 (s, 1
H), 8.77 (s, 1H). (Z) -1- {O- (4-methoxycarbonylbenzyl)
) -2,2-dimethyl-7-chromancarbohydroxy
Shimoyl｝ -1H-1,2,4-triazole (415
No.) NMR δ: 1.32 (s, 6H), 1.80 (t, 2H), 2.79 (t, 2H), 3.92
(s, 3H), 5.30 (s, 2H), 6.86 (dd, 1H), 6.89 (d, 1H), 7.07
(d, 1H), 7.42 (d, 2H), 8.04 (d, 2H), 8.07 (s, 1H), 8.76
(s, 1H). (Z) -1- ｛O- (1H-1,2,4-triazole
-1-ylmethyl) -2,2-dimethyl-7-chroman
Carbohydroxymoyl {-1H-1,2,4-tria
Zol (# 416) NMR δ: 1.33 (s, 6H), 1.81 (t, 2H), 2.80 (t, 2H), 6.08
(s, 2H), 6.83 (dd, 1H), 6.89 (s, 1H), 7.09 (d, 1H), 8.03
(d, 1H), 8.06 (s, 1H), 8.42 (s, 1H), 8.72 (s, 1H). (Z) -1- ｛O- (1,3-dioxolan-2-yl
Methyl) -2,2-dimethyl-7-chromancarbohydrate
Roximoyl {-1H-1,2,4-triazole (4
No. 17) NMR δ: 1.31 (s, 6H), 1.79 (t, 2H), 2.78 (t, 2H), 3.87
-4.00 (m, 4H), 4.27 (d, 2H), 5.23 (t, 1H), 6.90 (d, 1H),
6.92 (s, 1H), 7.07 (d, 1H), 8.03 (s, 1H), 8.90 (s, 1H). (Z) -1- {O- (2-furylmethyl) -2,2-di
Methyl-7-chromancarbohydroxymoyl｝ -1H
-1,2,4-triazole (# 418) NMR δ: 1.32 (s, 6H), 1.80 (t, 2H), 2.79 (t, 2H), 5.18
(s, 2H), 6.37 (d, 1H), 6.45 (d, 1H), 6.91 (d, 1H), 6.92
(s, 1H), 7.08 (d, 1H), 7.43 (d, 1H), 8.03 (s, 1H), 8.79
(s, 1H). (Z) -1- {O- (2,2-dimethyl-1,3-dio)
Oxolan-4-ylmethyl) -2,2-dimethyl-7-
Chromancarbohydroxymoyl｝ -1H-1,2,4
-Triazole (# 419) NMR δ: 1.33 (s, 6H), 1.37 (s, 3H), 1.42 (s, 3H), 1.81
(t, 2H), 2.80 (t, 2H), 3.80 (dd, 1H), 4.10 (dd, 1H), 4.24
-4.30 (m, 2H), 4.40-4.48 (m, 1H), 6.90 (d, 1H), 6.96 (s, 1
H), 7.11 (d, 1H), 8.51 (s, 1H), 8.88 (s, 1H). (Z) -1- {O- (2,3-dihydroxypropyl)
-2,2-dimethyl-7-chromancarboxyhydroxy
Ill｝ -1H-1,2,4-triazole (# 420) NMR δ: 1.32 (s, 6H), 1.80 (t, 2H), 2.79 (s, 2H), 3.55
-3.65 (m, 2H), 4.01-4.12 (m, 1H), 4.23-4.35 (m, 2H), 6.8
5-6.95 (m, 2H), 7.08 (d, 1H), 8.06 (s, 1H), 8.81 (s, 1H). (Z) -1- {O- (2-oxo-3-tetrahydrof)
Ranyl) -2,2-dimethyl-7-chroman carbohydrate
Roximoyl {-1H-1,2,4-triazole (4
# 21) NMR δ: 1.33 (s, 6H), 1.81 (t, 2H), 2.62-2.70 (m, 2H),
2.80 (t, 2H), 4.35 (dd, 1H), 4.49-4.57 (m, 1H), 5.06 (t,
1H), 6.88 (d, 1H), 6.93 (s, 1H), 7.09 (d, 1H), 8.08 (s, 1
H), 8.88 (s, 1H). (Z) -1- {O- (3-tetrahydrofuranyl)-
2,2-dimethyl-7-chromancarbohydroxymoi
｝ -1H-1,2,4-triazole (# 422) NMR δ: 1.33 (s, 6H), 1.81 (t, 2H), 2.14-2.21 (m, 2H),
2.80 (t, 2H), 3.82-3.93 (m, 3H), 4.09 (d, 1H), 5.00-5.0
5 (m, 1H), 6.90 (dd, 1H), 6.94 (d, 1H), 7.09 (d, 1H), 8.05
(s, 1H), 8.80 (s, 1H). (Z) -1- {O- (3-oxocyclopentenyl)-
2,2-dimethyl-7-chromancarbohydroxymoi
｝ -1H-1,2,4-triazole (No. 423) NMR δ: 1.35 (s, 6H), 1.83 (t, 2H), 2.55 (dd, 2H), 2.7
7 (dd, 2H), 2.84 (t, 2H), 5.91 (s, 1H), 6.95 (s, 1H), 6.96
(d, 1H), 7.16 (d, 1H), 8.15 (s, 1H), 8.74 (s, 1H). (E, Z) -1- {O- (1,3-oxazoline-2-
Ilmethyl) -2,2-dimethyl-7-chromancarb
Hydroxymoyl-1H-1,2,4-triazole
(# 424) NMR δ: 1.32 (s, 4.8H), 1.34 (s, 1.2H), 1.80 (t, 2H),
2.79 (t, 2H), 3.92 (t, 2H), 4.33 (t, 2H), 4.83 (s, 0.4H),
4.88 (s, 1.6H), 6.92 (d, 1H), 6.93 (s, 1H), 7.09 (d, 1H),
8.04 (s, 0.2H), 8.06 (s, 0.8H), 8.55 (s, 0.2H), 9.12 (s,
0.8H). (E) -1- (O-acetyl-2,2-dimethyl-7-
Chromancarbohydroxymoyl) -1H-1,2,4
-Triazole (# 425) NMR δ: 1.36 (s, 6H), 1.85 (t, 2H), 2.19 (s, 3H), 2.85
(t, 2H), 6.90-7.22 (m, 3H), 8.08 (s, 1H), 8.79 (s, 1H). (Z) -1- ｛O- (N, N-dimethylcarbamoyl)
-2,2-dimethyl-7-chromancarboxyhydroxy
Ill-1H-1,2,4-triazole (# 426) NMR δ: 1.32 (s, 6H), 1.81 (t, 2H), 2.81 (t, 2H), 2.82
(s, 3H), 3.00 (s, 3H), 6.91 (s, 1H), 7.11 (s, 2H), 8.59
(s, 1H), 8.86 (s, 1H). (Z) -1- (O-i-propyl-2,2,7-trime
Tyl-5-chromancarbohydroxymoyl) -1H-
1,2,4-triazole (No. 427) NMR δ: 1.00 (s, 6H), 1.36 (d, 6H), 1.72 (t, 2H), 2.29
(s, 3H), 2.70 (t, 2H), 4.54 (quintet, 1H), 6.99 (s, 1H),
7.17 (s, 1H), 7.89 (s, 1H), 9.01 (s, 1H). (Z) -1- (2,2-dimethyl-6-chloro-7-c
Romancarbohydroxymoyl) -1H-1,2,4-
Triazole (No. 428) NMR δ: 1.34 (s, 6H), 1.81 (t, 2H), 2.79 (t, 2H), 7.03
(s, 1H), 7.13 (s, 1H), 8.02 (s, 1H), 9.18 (s, 1H), 9.28-
9.35 (m, 1H). (E) -1- (2,2-Dimethyl-6-chloro-7-k)
Romancarbohydroxymoyl) -1H-1,2,4-
Triazole (E-form contained in No. 429) NMR δ: 1.33 (s, 3H), 1.59 (s, 3H), 1.82 (t, 2H), 2.80
(t, 2H), 6.90-7.08 (m, 2H), 8.12 (s, 1H), 8.73-8.79 (m, 1
H), 8.83 (s, 1H). (Z) -1- (O-ethoxymethyl-2,2-dimethyl
-6-chloro-7-chromancarbohydroxymoyl)
-1H-1,2,4-triazole (# 430) NMR δ: 1.25 (t, 3H), 1.34 (s, 6H), 1.80 (t, 2H), 2.78
(t, 2H), 3.75 (q, 2H), 5.35 (s, 2H), 7.03 (s, 1H), 7.11
(s, 1H), 7.98 (s, 1H), 9.18 (s, 1H). (E) -1- (O-ethoxymethyl-2,2-dimethyl
-6-chloro-7-chromancarbohydroxymoyl)
-1H-1,2,4-triazole (included in No. 431
NMR δ: 1.23 (t, 3H), 1.33 (s, 6H), 1.81 (t, 2H), 2.80
(t, 2H), 3.71 (q, 2H), 5.28 (s, 2H), 6.94-7.07 (m, 2H),
8.08 (s, 1H), 8.78 (s, 1H). (Z) -1- {O- (2-propynyl) -2,2-dimethyl
Cyl-6-chloro-7-chromancarbohydroxymoy
｝ -1H-1,2,4-triazole (No. 432) NMR δ: 1.34 (s, 6H), 1.80 (t, 2H), 2.58 (t, 1H), 2.78
(t, 2H), 4.89 (d, 2H), 7.03 (s, 1H), 7.11 (s, 1H), 7.98
(s, 1H), 9.17 (s, 1H). (Z) -1- (O-acetyl-2,2-dimethyl-6-)
Chlor-7-chromancarbohydroxymoyl) -1H
-1,2,4-triazole (No. 433) NMR δ: 1.34 (s, 6H), 1.81 (t, 2H), 2.34 (s, 3H), 2.79
(t, 2H), 7.11 (s, 1H), 7.12 (s, 1H), 8.04 (s, 1H), 9.07
(s, 1H). (Z) -1- (O-isobutyryl-2,2-dimethyl-
6-chloro-7-chromancarbohydroxymoyl)-
1H-1,2,4-triazole (# 434) NMR δ: 1.33 (s, 6H), 1.33 (d, 6H), 1.81 (t, 2H), 2.79
(t, 2H), 2.81 (septet, 1H), 7.11 (s, 1H), 7.14 (s, 1H),
8.05 (s, 1H), 9.03 (s, 1H). (Z) -1- {O- (t-butoxycarbonyl) -2,
2-dimethyl-6-chloro-7-chromancarbohydro
Ximoyl {-1H-1,2,4-triazole (43
No. 5) NMR δ: 1.32 (s, 6H), 1.58 (s, 9H), 1.80 (t, 2H), 2.78
(t, 2H), 7.11 (s, 2H), 8.02 (s, 1H), 9.18 (s, 1H). (Z) -1- ｛O- (N, N-dimethylcarbamoyl)
-2,2-dimethyl-6-chloro-7-chromancarbo
Hydroxymoyl-1H-1,2,4-triazole
(# 436) NMR δ: 1.33 (s, 6H), 1.80 (t, 2H), 2.78 (t, 2H), 3.00
-3.10 (m, 6H), 7.09 (s, 1H), 7.16 (s, 1H), 8.05 (s, 1H),
8.93 (s, 1H). (Z) -1- (O-isopropyl-2,2,3-trime
Tyl-7-chromancarbohydroxymoyl) -1H-
1,2,4-triazole (# 437) NMR δ: 1.02 (d, 3H), 1.16 (s, 3H), 1.32 (d, 6H), 1.37
(s, 3H), 1.80-2.00 (m, 1H), 2.48 (dd, 1H), 2.99 (dd, 1H),
4.52 (quintet, 1H), 6.89 (dd, 1H), 6.96 (d, 1H), 7.05 (d,
1H), 8.05 (s, 1H), 9.19 (s, 1H). 1- (N, N-dimethyl-2,2-dimethyl-7-chloro
Mancarbohydrazonoyl) -1H-1,2,4-tri
Azole (# 438) NMR δ: 1.31 (s, 6H), 1.79 (t, 2H), 2.59 (s, 6H), 2.76
(t, 2H), 6.74 (dd, 1H), 6.77 (d, 1H), 7.00 (d, 1H), 8.14
(s, 1H), 8.43 (s, 1H). 1- (N, N-dimethyl-2,2-dimethyl-7-chloro
Mancarbohydrazonoyl) -imidazole (439)
No.) NMR δ: 1.35 (s, 6H), 1.80 (t, 2H), 2.52 (s, 6H), 2.78
(t, 2H), 6.80 (dd, 1H), 6.89 (d, 1H), 7.02 (d, 1H), 7.16
(d, 1H), 7.18 (s, 1H), 7.72 (s, 1H). 1- {N- (1-piperidyl) -2,2-dimethyl-7
-Chromancarboxymidyl-1H-1,2,4-
Triazole (No. 440) (DMSO-d ₆ NMR δ: 1.25 (s, 6H), 1.40-1.60 (m, 6H), 1.75 (t, 2H),
2.68 (t, 4H), 2.73 (t, 2H), 6.51 (d, 1H), 6.73 (dd, 1H),
7.06 (d, 1H), 8.28 (s, 1H), 8.92 (s, 1H). (E, Z) -1- {N- (1-piperidyl) -2,2-
Dimethyl-7-chromancarboximidoyl {-1H-
1,2,4-triazole (# 441) NMR δ: 1.32 (s, 3.6H), 1.34 (s, 2.4H), 1.40-1.50 (m,
2.4H), 1.50-1.70 (m, 3.6H), 1.79 (t, 1.2H), 1.83 (t, 0.8
H), 2.70 (t, 2.4H), 2.78 (t, 1.2H), 2.81 (t, 1.6H), 2.87
(t, 0.8H), 6.84 (dd, 1H), 6.90 (d, 1H), 7.03 (d, 0.6H),
7.12 (d, 0.4H), 7.96 (s, 0.4H), 8.10 (s, 0.6H), 8.54 (s,
0.4H), 8.73 (s, 0.6H). (4-Fluorobenzylidenehydrazono)-(2,2-
Dimethyl-chroman-7-yl)-(1H-1,2,4
-Triazol-1-yl) methane (# 442) NMR δ: 1.35 (s, 6H), 1.83 (t, 2H), 2.84 (t, 2H), 7.05
-7.20 (m, 5H), 7.75 (dd, 2H), 8.10 (s, 1H), 8.65 (s, 1H),
8.72 (s, 1H). (3-Methyl-2-butylidenehydrazono)-(2,2
-Dimethyl-chroman-7-yl)-(1H-1,2,2,
4-triazol-1-yl) methane (No. 443) NMR δ: 1.08 (d, 6H), 1.33 (s, 6H), 1.81 (t, 2H), 2.03
(s, 3H), 2.53 (septet, 1H), 2.80 (t, 2H), 7.09 (s, 1H),
7.25 (t, 2H), 8.02 (s, 1H), 8.55 (s, 1H). (E, Z) -1- (N, N-dimethyl-2,2,6-to
Limethyl-7-chromancarbohydrazonoyl) -1H
-1,2,4-triazole (# 444) NMR δ: 1.31 (s, 1.5H), 1.33 (s, 4.5H), 1.75-1.83 (m,
2H), 2.05 (s, 3H), 2.58 (s, 1.5H), 2.63 (s, 4.5H), 2.70-
2.80 (m, 2H), 6.71 (s, 1H), 6.88 (s, 0.25H), 6.97 (s, 0.75
H), 7.94 (s, 0.75H), 8.01 (s, 0.25H), 8.46 (s, 0.75H),
9.03 (s, 0.25H). (Z) -1- (O-isopropyl-2-methyl-1,4
-Benzodioxane-7-carbohydroxymoyl)-
1H-1,2,4-triazole (No. 445) NMR δ: 1.32 (d, 6H), 1.36 (d, 3H), 3.80-3.90 (m, 1H),
4.20-4.35 (m, 2H), 4.52 (septet, 1H), 6.88 (d, 1H), 6.9
9 (dd, 1H), 7.04 (d, 1H), 8.05 (s, 1H), 8.84 (s, 1H). (Z) -1- (O-isopropyl-2-ethyl-1,4
-Benzodioxane-7-carbohydroxymoyl)-
1H-1,2,4-triazole (# 446) NMR δ: 1.07 (t, 3H), 1.32 (d, 6H), 1.59-1.82 (m, 2H),
3.82-3.96 (m, 1H), 3.99-4.15 (m, 1H), 4.21-4.31 (m, 1
H), 4.52 (septet, 1H), 6.88 (d, 1H), 6.94-7.06 (m, 2H),
8.05 (s, 1H), 8.84 (s, 1H). (Z) -1- (O-isopropyl-2-t-butyl-
1,4-benzodioxane-7-carbohydroxymoy
M) -1H-1,2,4-triazole (# 447) NMR δ: 1.04 (t, 9H), 1.33 (d, 6H), 3.75 (dd, 1H), 3.9
3 (dd, 1H), 4.39 (dd, 1H), 4.53 (septet, 1H), 6.88 (d, 1H),
6.96 (dd, 1H), 7.06 (d, 1H), 8.06 (s, 1H), 8.85 (s, 1H). (Z) -1- (O-isopropyl-2-phenyl-1,
4-benzodioxane-7-carbohydroxymoyl)
-1H-1,2,4-triazole (# 448) NMR δ: 1.33 (d, 6H), 4.06 (dd, 1H), 4.41 (dd, 1H), 4.
53 (septet, 1H), 5.14 (dd, 1H), 6.96 (d, 1H), 7.06 (dd, 1H
H), 7.18 (d, 1H), 7.35-7.48 (m, 5H), 8.06 (s, 1H), 8.87
(s, 1H). (Z) -1- (O-isopropyl-2,2-dimethyl-
1,4-benzodioxane-7-carbohydroxymoy
Le) -1H-1,2,4-triazole (# 449) NMR δ: 1.32 (d, 6H), 1.35 (s, 6H), 3.91 (s, 2H), 4.51
(septet, 1H), 6.88 (d, 1H), 6.97 (dd, 1H), 7.04 (d, 1H),
8.05 (s, 1H), 8.82 (s, 1H). (Z) -1- (O-isopropyl-2,3-dimethyl-
1,4-benzodioxane-7-carbohydroxymoy
Le) -1H-1,2,4-triazole (# 450) NMR δ: 1.32 (d, 6H), 1.35-1.40 (m, 6H), 3.80-4.10
(m, 2H), 4.52 (septet, 1H), 6.83-7.06 (m, 3H), 8.05 (s, 1
H), 8.83 (s, 1H). (Z) -1- (O-isopropyl-2,2-dimethyl-
1,4-benzodioxane-6-carbohydroxymoy
M) -1H-1,2,4-triazole (# 451) NMR δ: 1.32 (d, 6H), 1.36 (s, 6H), 3.89 (s, 2H), 4.52
(septet, 1H), 6.85 (d, 1H), 6.99 (dd, 1H), 7.08 (d, 1H),
8.06 (s, 1H), 8.84 (s, 1H). (E) -1- (O-isopropyl-2,2-dimethyl-
1,4-benzodioxane-6-carbohydroxymoy
Le) -1H-1,2,4-triazole (# 452) NMR δ: 1.35 (d, 6H), 1.37 (s, 6H), 3.90 (s, 2H), 4.48
(septet, 1H), 6.87 (d, 1H), 7.06 (dd, 1H), 7.21 (d, 1H),
8.05 (s, 1H), 8.54 (s, 1H). (Z) -1- (O-isopropyl-2,2-dimethyl-
6-chloro-1,4-benzodioxane-7-carbohi
Droximoyl) -1H-1,2,4-triazole
(# 453) NMR δ: 1.36 (s, 6H), 1.38 (d, 6H), 3.90 (s, 2H), 4.57
(septet, 1H), 6.96 (s, 1H), 7.05 (s, 1H), 7.96 (s, 1H),
9.20 (s, 1H). (E, Z) -1- (N, N-dimethyl-1,4-benzo)
Dioxane-6-carbohydrazonoyl) -1H-1,
2,4-triazole (# 454) NMR δ: 2.56 (s, 4H), 2.64 (s, 2)
H), 4.25 (s, 2.7H), 4.30 (s,
1.3H), 6.80-6.88 (m, 2H),
6.90-7.07 (m, 1H), 7.96 (s,
0.3H), 8.15 (s, 0.7H), 8.49
(S, 0.7H), 8.56 (s, 0.3H). 1- (N, N-dimethyl-6-chloro-1,4-benzo
Dioxane-7-carbohydrazonoyl) -1H-1,
2,4-triazole (# 455) NMR δ: 2.69 (s, 6H), 4.30 (s, 4)
H), 6.98 (s, 1H), 7.00 (s, 1)
H), 7.93 (s, 1H), 8.59 (s, 1)
H). 1- (N, N-dimethyl-6-chloro-1,4-benzo
Dioxane-7-carbohydrazonoyl) -imidazo
(# 456) NMR δ: 2.55 (s, 6H), 4.32 (s, 4H), 6.92 (s, 1H), 7.02
(s, 1H), 7.01-7.08 (m, 1H), 7.24-7.29 (m, 1H), 7.58-7.6
2 (m, 1H). 1- (N, N-dimethyl-6-iodo-1,4-benzo
Dioxane-7-carbohydrazonoyl) -1H-1,
2,4-triazole (No. 457) NMR δ: 2.72 (s, 6H), 4.29 (s, 4H), 6.97 (s, 1H), 7.38
(s, 1H), 7.94 (s, 1H), 8.59 (s, 1H). (E, Z)-(N, N-dimethyl-6-cyano-1,4
-Benzodioxane-7-carbohydrazonoyl) -1
H-1,2,4-triazole (# 458) NMR δ: 2.70 (s, 2.4H), 2.79 (s, 3.6H), 4.27 (s, 2.4
H), 4.36 (s, 1.6H), 6.29 (s, 0.6H), 7.07 (s, 0.4H), 7.22
(s, 0.4H), 7.26 (s, 0.6H), 7.94 (s, 0.4H), 8.14 (s, 0.6
H), 8.47 (s, 0.6H), 8.73 (s, 0.4H). (Z) -1- (O-isopropyl-6-chloro-1,4)
-Benzodioxene-7-carbohydroxymoyl)-
Imidazole (# 459) NMR δ: 1.35 (d, 6H), 4.49 (septet, 1H), 5.90 (s, 2H),
6.70 (s, 1H), 6.77 (s, 1H), 7.06 (s, 1H), 7.16 (s, 1H),
8.09 (s, 1H). (E, Z) -1- (N, N-dimethyl-1,4-benzo)
Dioxene-6-carbohydrazonoyl) -1H-1,
2,4-triazole (# 460) NMR δ: 2.59 (s, 4.8H), 2.66 (s, 1.2H), 5.86 (s, 1.6)
H), 5.89 (s, 0.4H), 6.51-6.69 (m, 3H), 7.96 (s, 0.2H),
8.15 (s, 0.8H), 8.41 (s, 0.8H), 8.58 (s, 0.2H). (Z) -1- (O-isopropyl-3,3-dimethyl-
2,3-dihydro-1,4-benzoxazine-6-ca
Rubohydroxymoyl) -1H-1,2,4-triazo
(# 461) NMR δ: 1.23 (s, 6H), 1.31 (d, 6H), 3.61 (br.s, 1H),
3.85 (s, 2H), 4.50 (septet, 1H), 6.70-6.85 (m, 3H), 8.05
(s, 1H), 8.79 (s, 1H). (Z) -1- (O-isopropyl-3,3-dimethyl-
2,3-dihydro-4-acetyl-1,4-benzooxy
Sagin-6-carbohydroxymoyl) -1H-1,
2,4-triazole (# 462) NMR δ: 1.34 (d, 6H), 1.54 (s, 6H), 2.25 (s, 3H), 3.89
(s, 2H), 4.53 (septet, 1H), 6.94 (d, 1H), 7.12-7.21 (m, 2
H), 8.06 (s, 1H), 8.88 (s, 1H). (Z) -1- (O-isopropyl-3,3,4-trimer
Tyl-2,3-dihydro-1,4-benzoxazine-
6-carbohydroxymoyl) -1H-1,2,4-to
Riazol (No. 463) NMR δ: 1.20 (s, 6H), 1.32 (d, 6H), 2.75 (s, 3H), 3.91
(s, 2H), 4.53 (septet, 1H), 6.63-6.80 (m, 3H), 8.05 (s, 1
H), 8.83 (s, 1H). (E) -1- (O-isopropyl-7-bromo-1,4
-Benzodioxane-6-carbohydroxymoyl)-
1H-1,2,4-triazole (No. 538) NMR δ: 1.32 (d, 6H), 4.25-4.32 (m, 4H), 4.53 (septe
(t, 1H), 6.86-7.17 (m, 2H), 8.05 (s, 1H), 8.86 (s, 1H).

[0141]

[Formulation Examples] Next, the formulation method will be specifically described with reference to typical formulation examples. The type and compounding ratio of the compound additive
The present invention is not limited to this, and can be changed in a wide range. In the following description, “%” indicates weight percentage.

[0142]

Formulation Example 1 (Emulsion) To 20% of compound No. 1 was added and dissolved 65% of a mixed solution of xylene-methylnaphthalene, and then a mixture of alkylphenol ethylene oxide condensate and calcium alkylbenzene sulfonate (8: 2 ) 15% to form an emulsion. The drug is diluted with water and used as a spray liquid.

[0143]

Formulation Example 2 (Hydrate) 20% of No. 1 compound is 35% kaolin, 30% clay,
A mixture of 7.5% diatomaceous earth and a mixture of sodium laurate and sodium dinaphthylmethanesulfonate (1: 1)
7.5% was mixed and pulverized to obtain a wettable powder. The drug is diluted with water and used as a spray liquid.

[0144]

Formulation Example 3 (Powder) 97% of a mixture of talc and calcium carbonate (1: 1) is added to 1% of the No. 1 compound, and the mixture is ground and sufficiently dispersed and blended, and then 2% of silicic anhydride is further added. It was added, mixed and pulverized to obtain a powder. Spray this drug as it is.

[0145]

Formulation Example 4 (Granules) Compound No. 1 (2%) was mixed with bentonite fine powder (48%), talc (48%), and sodium ligninsulfonate (2%), and then kneaded until uniform by adding water. Next, the mixture was granulated through an injection molding machine and dried to obtain granules. Spray this agent as it is on the soil surface.

[0146]

Formulation Example 5 (Oil) 0.1% compound No. 1 and 0.5% piperonyl butoxide
% And dissolved in white kerosene to make the whole 100% to obtain an oil agent. Use this drug as is.

[0147]

[Formulation Example 6] (Floable agent) 5% of No. 1 compound, 5% of Newkalgen (dispersing agent manufactured by Takemoto Yushi Co., Ltd.), 0.2% of Antifoam 422 (defoaming agent manufactured by Rhone-Plain) and distilled water Mix 72.8%, 1,000rpm
After milling for 45 minutes, 8% of propylene glycol, 2% of xanthan gum and 7% of 1% Proxcel GXL solution were added and mixed. This agent (5% flowable agent) is diluted with water and used as a spray liquid.

[0148]

Industrial Applicability The oxime, hydrazone or azine derivative of the present invention exhibits an extremely excellent controlling effect, particularly against hemiptera pests. Particularly useful plants that attack crops and flowering trees, such as whitefly, whitefly, whitefly, cotton aphid, snowy aphid, apple cotton aphid, peach peach aphid, radish aphid, mushroom aphid, bean aphid, and citrus aphid Aphids,
Potato beetle aphid, corn leafhopper, leafhopper leafhopper, brown planthopper, brown planthopper, sagebill planthopper, black leafhopper, yanonekaiyushita, kuwakonikaigaushi, mikankonikaigai, ishierikaishiba, southern green mosquito
It has an excellent insecticidal activity against Hemiptera pests such as P. aeruginosa, Nashigunbai, pear lice and apple lice, and shows an excellent control effect.

In addition, thrips, Thrips palmi, Thrips palmi, Thrips palmi,
It also has an insecticidal activity against Thripidae insects such as Thrips palmi and Thrips palmi, and exhibits excellent control effects.

[0150] Away armyworm, Tamana-yaga, Shiroitimo-jimyo-to, Spodoptera litura, Heliotis, Kabra-Yaga,
Iyotoga, Tamanaginiwawa, Nikameiga, Kobunomeiga, Himadarameiga, Inetomimushi, Cottonweed Beetle, Monshiro Butterfly, Anthropomorphus persicae, Apple Scared Monmonamaki, Midarekakumon Hamasaki, Tohokuhagama, Tohomahosogamiga, Tohomahoganigamogomi, Tohokuhomaogomaigamoganogomagomi, Homomonogoshigomagi
Lepidopteran pests such as bean squirrels, peach squirrels, grape scabbards, oaks, scallops, sugas, etc., rice water weevil, rice dwarf beetle, cypress flea beetle, colorado leaf beetle, turtle beetle, Diabrotica spp, coccinella, adzuki beetle, citrus beetle,
Coleoptera pests such as stilt beetles, tobacco beetles, pitted beetles, scorpion beetles, and beetle beetles, Culex pipiens, Culex pipiens, Aedes albopictus,
Diptera pests such as rice leaf fly, soybean falcon, rice carabid, rice paddy fly, house fly, onion fly, turtle fly, citrus fly, bean leaf fly, black cockroach, black cockroach, brown cockroach,
It also has insecticidal activity against insects of the order Orthoptera, such as German cockroaches, Japanese locusts, and Tosama locusts, and the insects of the order Hymenoptera, such as the wasps, and shows a controlling effect.

Further, the compound of the present invention has a property of transferring from the leaf surface to the back surface. By treating the compound of the present invention on the leaf surface, not only pests which come into direct contact with the compound of the present invention but also compounds of the present invention It also has insecticidal activity against pests parasitic on the back of leaves that do not come into direct contact with water, and has a controlling effect.

The oxime, hydrazone or azine derivative of the present invention also has acaricidal activity against spider mites such as spider mites and spider mites parasitic on fruit trees, vegetables and flowers.

It also has acaricidal activity against ticks, mites, parasitoids, etc., which are parasitic on animals.

In addition, the mobility of ectoparasitic nematodes such as the nematode, nematode, and nematode species, semi-internal parasitic nematode such as the Tylenx species, the nematode nematode species, the radholus species, and the nematode species Plant parasites such as endoparasitic nematodes, established endoparasitic nematodes such as cyst nematode species, potato cyst nematode species, and root-knot nematode species, such as aferecoilus species and nemogli nematode species represented by ditilenx species and pine wood nematodes It also has nematicidal activity against sex nematodes.

Further, the compounds of the present invention also have fungicidal activity, such as rice blast, rice sheath blight, cucumber downy mildew, cucumber gray mold, cucumber powdery mildew, cucumber spot bacterial disease and Komatsuna black soot disease. Can be effectively controlled.
In particular, the compound of the present invention showed an effective control effect in a cucumber powdery mildew control test.

[0156]

[Test Examples] The effects of the present invention will be described more specifically with reference to test examples below, but the effects of the present invention are not limited to those described in the following test examples.

[0157]

Test Example 1 Insecticidal Test of Brown Planthopper (Foliage Dipping Method) An emulsion prepared according to Formulation Example 1 was prepared by adding 500 p.
pm with water. Rice foliage was immersed in the chemical solution, air-dried, and allowed to stand in a glass cylinder. The 10th instar larvae of the brown planthopper, 10 larvae, were released into the larvae, and the larvae were covered with a medicine wrapper. Then, it was placed in a constant temperature room at 25 ° C., and after 5 days, the number of dead insects was examined, and the mortality was calculated. The test was performed in a two-part system. The following compounds showed 100% insecticidal activity.

1, 2, 11, 33, 64, 65, 67,
68, 69, 70, 74, 78, 81, 100, 10
2, 105, 108, 109, 110, 119, 12
1, 122, 123, 124, 125, 126, 12
8, 129, 130, 131, 133, 141, 14
3, 156, 164, 165, 166, 304, 30
5, 314, 359, 389, 406, 408, 41
1, 412, 430, 432, 437, 438, 43
9, 445, 446, 447, 449, 450, 45
1, 453, 459, 461, 462, 463 and 53
No. 8 compound.

[0159]

[Test Example 2] Insecticidal test of brown planthopper (root immersion method) A wettable powder prepared according to Formulation Example 2 was formulated using 50p of active ingredient.
pm with water. The rice root was immersed in the chemical solution, left for 2 days, and then allowed to stand in a glass cylinder. The 10th instar larvae of the brown planthopper, 10 larvae, were released into the larvae, and the larvae were covered with a medicine wrapper. Then, it was placed in a constant temperature room at 25 ° C., and after 5 days, the number of dead insects was examined, and the mortality was calculated. The test was performed in a two-part system. The following compounds showed 100% insecticidal activity.

1, 67, 68, 70, 78, 81, 10
0, 102, 105, 108, 119, 121, 12
2, 123, 124, 125, 126, 128, 12
9, 131, 133, 141, 156, 164, 40
1,402,403,411,432,444,44
5, 446, 449, 450, 453, 454, 45
Compounds # 5, 456, 457, 461, 463 and 538.

[0161]

[Test Example 3] Insecticidal test of leafhopper leafhopper (foliage dipping method) An emulsion prepared according to Formulation Example 1 was prepared using an active ingredient of 500 p.
pm with water. Rice foliage was immersed in the chemical solution, air-dried, and allowed to stand in a glass cylinder. Ten larvae of the third instar larvae were released into the larvae, and the larvae were covered with medicine wrapping paper. Then, it was placed in a constant temperature room at 25 ° C., and after 5 days, the number of dead insects was examined, and the mortality was calculated. The test was performed in a two-part system. The following compounds showed 100% insecticidal activity.

1, 2, 64, 65, 67, 68, 69,
70, 74, 78, 81, 100, 102, 121, 1
22, 123, 124, 125, 128, 129, 13
0, 141, 304, 305, 314, 359, 41
1, 412, 425, 432, 433, 434, 43
6, 437, 442, 444, 445, 446, 44
7, 449, 450, 451, 453, 461, 462
And the compound of No. 463.

[0163]

Test Example 4 Insecticidal test of leafhopper leafhopper (root dipping method) A wettable powder prepared according to Formulation Example 2 was prepared by adding 50p of active ingredient.
pm with water. The rice root was immersed in the chemical solution, left for 2 days, and then allowed to stand in a glass cylinder. Ten larvae of the third instar larvae were released into the larvae, and the larvae were covered with medicine wrapping paper. Then, it was placed in a constant temperature room at 25 ° C., and after 5 days, the number of dead insects was examined, and the mortality was calculated. The test was performed in a two-part system. The following compounds showed 100% insecticidal activity.

67, 70, 81, 121, 123, 12
4, 125, 128, 141, 156, 394, 41
7, 427, 437, 442, 444, 445, 44
Compounds 9, 453, 460, 461, 462 and 463.

[0165]

Test Example 5 Cotton Aphid Insecticidal Test The cotton aphid adult was used for leaf cucumber leaf disk (4.
(5 cm × 4.5 cm). After the larvae were allowed to grow for 18 hours, the adults were removed and the number of parasites was adjusted so that there were 5 larvae per leaf disk. The emulsion prepared according to Formulation Example 1 was diluted with water so that the active ingredient content was 500 ppm, and 2 ml of the diluted solution was sprayed on a leaf disk using a rotary spray tower. The processed leaf disk is
Place on absorbent cotton moistened with water so that the parasitic surface is on top,
It was placed in a seal container and kept in a constant temperature room at 25 ° C. Five days after the treatment, the number of dead insects was examined, and the mortality was calculated. The test was performed in a two-part system. The following compounds showed 100% insecticidal activity.

1, 2, 11, 33, 64, 65, 67,
68, 69, 70, 74, 78, 81, 100, 10
8, 109, 110, 119, 121, 122, 12
3, 124, 125, 126, 128, 129, 13
0, 143, 164, 165, 166, 304, 30
5, 314, 359, 389, 401, 402, 40
3, 404, 411, 426, 430, 432, 43
7, 438, 439, 444, 445, 446, 44
7, 449, 450, 453, 459, 461 and 53
No. 8 compound.

[0167]

Test Example 6 Transferability from Leaf Surface to Back Surface Ten first-instar cotton aphid larvae were released to the back of a potted cucumber (3-4 leaf stage), and the back of the leaf was covered with an acrylic plate. An emulsion prepared according to Formulation Example 1 was mixed with an active ingredient of 50%.
It was diluted with water to 0 ppm. A sufficient amount of this solution was sprayed on the opposite side (leaf surface) of the aphid-fixing surface, and kept in a constant temperature room at 23 ° C. Two days after the treatment, the number of dead insects was examined, and the mortality was calculated. As a result, the compound of the present invention showed particularly excellent insecticidal activity.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁶ Identification number Agency reference number FI Technical display location A01N 47/42 A01N 47/42 A C07D 249/08 529 C07D 249/08 529 405/06 233 405 / 06 233 249 249 411/06 411/06 413/06 233 413/06 233 249 249 (72) Inventor Soji Mizugai 1041 Yasu-cho, Yasu-cho, Yasu-gun, Shiga Prefecture Sankyo Stock Company In-house (72) Inventor Reiji Ichinose Yasu-gun, Shiga Prefecture 1041 Yasucho Yasu, Sankyo Stock Company In-house (72) Inventor Hiromi Sano 1041 Nosumachi Yasucho, Yasu-gun, Shiga Prefecture Sankyo Stock Company In-house (72) Inventor Tetsuya Toya 6-7-8, Kamiochiai 201, Yono-shi, Saitama (72) Invention Applicant Yasuhito Kato 6-7-111 Kamiochiai, Yono-shi, Saitama Prefecture (72) Inventor Seiichiro Kodama 6-2-21-2, Kamiochiai, Yono-shi, Saitama Prefecture Inventor Toshiaki Iwasaki 6-11-15 Kamiochiai, Yono City, Saitama Prefecture (72) Inventor Tetsuo Watanabe 880-33, Koshigaya, Ageo City, Saitama Prefecture (72) Inventor Atsushi Iwabuchi 6-7-8, Kamiochiai, Yono City, Saitama Prefecture 205

Claims (12)

[Claims] 1. A compound represented by the following general formula (I): [In the above formula, the formula Is the following condensed ring group (condensed ring group) (Wherein R ⁴ represents a hydrogen atom, a C1-C3 alkyl group or a C2-C6 acyl group, and p represents 0, 1 or 2), and R ¹ represents a halogen. An atom, a C1-C6 alkyl group, a C1-C6 alkoxy group or a phenyl group, wherein R ² is a halogen atom, C1-C6
C6 alkyl group (the alkyl group may be 1 to 5 halogen atoms, 1 C1 to C6 alkoxy group, 1 C1 to
A C6 alkylthio group, which may be substituted with one C1 to C6 alkylsulfinyl group or one C1 to C6 alkylsulfonyl group, a C1 to C6 alkoxy group (the alkoxy group may be substituted with 1 to 5 halogen atoms, May be substituted), a C1-C6 alkylthio group,
A cyano group, a nitro group, a formyl group, a hydroxyl group or an amino group (the amino group may be substituted by one or two C1 to C3 alkyl groups), and R ³ is a group represented by OR ⁵ ; A group represented by NR ⁶ R ⁷ or N = CR ⁸ R ⁹
Wherein R ⁵ is a hydrogen atom, a C 1 -C 6 alkyl group, wherein the alkyl group has 1 to 5 halogen atoms,
One or two hydroxyl groups, one C1-C6 alkoxy group,
One C1-C6 alkylthio group, one C2-C6 alkoxycarbonyl group, one phenyl group (the phenyl group is a C1-C3 alkyl group, a halogen atom,
One or five substituents arbitrarily selected from a C6 alkoxycarbonyl group and a C2 to C6 acyl group; one 5- or 6-membered heterocyclic group (the heterocyclic group is , Having 1 to 3 atoms arbitrarily selected from an oxygen atom, a sulfur atom, and a nitrogen atom,
A C3 alkyl group, which may be substituted with a halogen atom or an oxo group, one C3-C6 cycloalkyl group (the cycloalkyl group may be substituted with one to three C1-C3 alkyl groups, a halogen atom or an oxo group; Substituted by one C3-C6 cycloalkenyl group (the cycloalkenyl group may be substituted by 1 to 3 C1-C3 alkyl groups, halogen atoms or oxo groups). May be present, C2-C
6 alkenyl groups (the alkenyl group may be substituted by 1 to 3 halogen atoms), C2 to C6 alkynyl groups (the alkynyl group may be substituted by 1 to 3 halogen atoms), A C3-C6 cycloalkyl group (the cycloalkyl group may be one to three C1
To C3 alkyl group, a halogen atom or an oxo group, and a C3 to C6 cycloalkenyl group (the cycloalkenyl group may be substituted by 1 to 3 C1 to C3 alkyl groups, a halogen atom or an oxo group). A C2 to C6 acyl group, a C2 to C6 alkoxycarbonyl group, a carbamoyl group (the nitrogen atom of the carbamoyl group may be substituted by a C1 to C6 alkyl group), or a 5- or 6-membered heterocyclic group Group (the heterocyclic group has 1 to 3 atoms arbitrarily selected from an oxygen atom, a sulfur atom, and a nitrogen atom, and has 1 to 3 C1 to C3
R ⁶ and R ⁷ may be the same or different and each represents a hydrogen atom or a C1-C6 alkyl group, or R ⁶ is an alkyl group, a halogen atom or an oxo group.
⁶ , R ⁷ may form a cyclic amino group together with an adjacent nitrogen atom, and R ⁸ and R ⁹ may be a hydrogen atom,
C6 alkyl group or phenyl group (the phenyl group is
M represents 0, 1, 2, 3, or 4 (m is 2, 3 or 4). In the case of 3 or 4, each R ¹ may be the same or different, and n represents 0, 1, 2 or 3 (n is 2 or 3
, Each R ² may be the same or different), and W represents CH or N. Or a salt thereof. 2. The compound according to claim 1, wherein the fused ring group is tetralin, chroman or benzodioxane, or a salt thereof. 3. The compound according to claim 1, wherein R ¹ is a halogen atom or a C1-C6 alkyl group, or a salt thereof. Wherein R ² is a halogen atom, (optionally substituted by the alkyl group one to five halogen atoms or one C1 -C6 alkoxy group) C1 -C6 alkyl, C1 -C6 4. The compound according to claim 1, which is an alkoxy group (the alkoxy group may be substituted by 1 to 5 halogen atoms), a C1 to C6 alkylthio group, a cyano group or a nitro group. 5. The compound according to claim 1, wherein R ² is a halogen atom, or a salt thereof. 6. A compound according to claim 1, wherein R ⁵ is a C1 to C6 alkyl group (the alkyl group is one to five halogen atoms or one C1 to C6 alkyl group).
6 may be substituted by an alkoxy group).
A compound or a salt thereof according to claim 1. 7. The compound according to claim 1, wherein R ⁵ is an unsubstituted C1-C6 alkyl group or a salt thereof. 8. The compound according to claim 1, wherein R ⁴ is a hydrogen atom, a methyl group or an acetyl group, or a salt thereof. 9. The compound according to claim 1, wherein R ⁶ and R ⁷ are a methyl group, or a salt thereof. 10. The method according to claim 1, wherein n is 0 or 1.
Or a salt thereof. 11. The compound according to claim 1, wherein p is 0, or a salt thereof. 12. The compound according to claim 1, wherein W is N, or a salt thereof.