JPH05178704A - Aromatic compound, its production and pest-controlling drug containing the same compound as active component - Google Patents

Abstract

PURPOSE:To provide the subject new aromatic compounds having a remarkably high juvenile hormone-like effect and exhibiting a high controlling effect on various kinds of insect pests including those having acquired an increased resistance to already existing insecticides. CONSTITUTION:Compounds of formula I [R<1> is a (halo)alkyl, a (halo)alkoxy, a (halo)alkoxyalkyl, a (halo)alkenyl, a (halo)alkenyloxy, etc.; R<2> is a halogen; R<3> is H, a halogen or methyl; R<4> is H or methyl; R<5> is H, a (halo)alkyl, a (halo) alkoxy, a (halo)alkylthio, methoxymethyl, CN, CO2, etc.; (m)is 1 to 3; (n)is 1 to 5], e.g. 1-sec-butoxy-3-chloro-4-(4-methylbenzyloxy)benzene. The above- mentioned compound can be obtained by reacting a phenolic compound of formula II (M is H or an alkaline metal) with a compound of formula III (A is a halogen). The above-mentioned compounds exhibit various effects such as inhibition in metamorphosis to an imago, eclosion inhibition and sterilization of an imago.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to a novel aromatic compound, a process for producing the same, and a pest control agent containing the same as an active ingredient.

[0002]

2. Description of the Related Art The fact that certain aromatic compounds have a pest controlling effect has hitherto been disclosed in, for example, JP-A-50-1862.
No. 8 publication.

[0003]

However, these compounds are not always sufficient as active ingredients of pest control agents.

[0004]

SUMMARY OF THE INVENTION In view of the above situation, the present inventors have conducted diligent studies to find a compound having a better pest control effect, and as a result, the following general formula
The present invention was completed by finding that the aromatic compound represented by Chemical formula 6 (hereinafter referred to as the compound of the present invention) has extremely high juvenile hormone-like activity. That is, the present invention has the general formula

[0005]

[Chemical 6]

[In the formula, R ¹ is an alkyl group having 3 to 8 carbon atoms, an alkoxy group having 3 to 8 carbon atoms, and 3 carbon atoms.
~ 8 alkoxyalkyl groups, alkenyl groups having 3 to 8 carbon atoms, alkenyloxy groups having 3 to 8 carbon atoms,
Alkenyloxyalkyl group having 3 to 8 carbon atoms, haloalkyl group having 3 to 8 carbon atoms, haloalkoxy group having 3 to 8 carbon atoms, haloalkoxyalkyl group having 3 to 8 carbon atoms, and 3 carbon atoms ~ 8 haloalkenyl groups,
Represents a haloalkenyloxy group having 3 to 8 carbon atoms, a haloalkenyloxyalkyl group having 3 to 8 carbon atoms, an alkynyloxy group having 3 to 8 carbon atoms, R ² represents a halogen atom, and R ³ represents Independently represent a hydrogen atom, a halogen atom or a methyl group, R ⁴ represents a hydrogen atom or a methyl group, R ⁵ independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or 1 to 4 carbon atoms Haloalkyl group, an alkoxy group having 1 to 4 carbon atoms, a haloalkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, a haloalkylthio group having 1 to 4 carbon atoms, 3,4- It represents a methylenedioxy group, a methoxymethyl group, a cyano group, a nitro group, m represents an integer of 1 to 3, and n represents an integer of 1 to 5. ] The aromatic compound shown by these, its manufacturing method, and the pest control agent which makes it an active ingredient are provided.

The compounds according to the invention have an excellent juvenile hormone-like activity against insects, which is markedly different from most conventional insecticides. That is, it exhibits effects such as inhibition of adult transformation, egg hatching, and adult sterilization. As a result, the compound of the present invention includes various pests, including pests that have developed resistance to existing insecticides, that is, agricultural, forestry and horticultural pests,
It mainly acts as a growth regulator, a sterilizing agent, an ovicide or a growth inhibitor against stored grain pests and sanitary pests, and exhibits a high control effect.

In the compound of the present invention represented by the general formula 6, the alkyl group having 3 to 8 carbon atoms represented by R ¹ is, for example, n-propyl group, isopropyl group or n-propyl group.
Butyl group, sec-butyl group, isobutyl group, tert-butyl group, n-pentyl group, neo-pentyl group, 2-methylbutyl group, 1-methylbutyl group, 1-ethylpropyl group, 1,1-dimethylpropyl group, n-hexyl group, 1
-Methylpentyl group, 2-methylpentyl group, 3-methylpentyl group, 4-methylpentyl group, 3,3-dimethylbutyl group, 2,2-dimethylbutyl group, 1,1-dimethylbutyl group, 2-ethylbutyl Group, 1-ethylbutyl group, 1,3-dimethylbutyl group, n-heptyl group, 5-
Methylhexyl group, 4-methylhexyl group, 3-methylhexyl group, 2-methylhexyl group, 1-methylhexyl group, 3-ethylpentyl group, 2-ethylpentyl group,
1-ethylpentyl group, 4,4-dimethylpentyl group,
3,3-dimethylpentyl group, 2,2-dimethylpentyl group, 1,1-dimethylpentyl group, n-octyl group,
6-methylheptyl group, 5-methylheptyl group, 4-methylheptyl group, 3-methylheptyl group, 2-methylheptyl group, 1-methylheptyl group, 1-ethylhexyl group, 1-propylpentyl group, 3-ethylhexyl group Base,
5,5-dimethylhexyl group, 4,4-dimethylhexyl group, 2,2-diethylbutyl group, 3,3-diethylbutyl group, 1-methyl-1-propylbutyl group, and the like,

The alkoxy group having 3 to 8 carbon atoms represented by R ¹ is, for example, n-propoxy group, isopropoxy group, n-butoxy group, sec-butoxy group, isobutoxy group, tert-butoxy group, n-pentyloxy group, ne
o-Pentyloxy group, 2-methylbutoxy group, 1-methylbutoxy group, 1-ethylpropoxy group, 1,1-dimethylpropoxy group, n-hexyloxy group, 1-methylpentyloxy group, 2-methylpentyloxy group Base, 3
-Methylpentyloxy group, 4-methylpentyloxy group, 3,3-dimethylbutoxy group, 2,2-dimethylbutoxy group, 1,1-dimethylbutoxy group, 2-ethylbutoxy group, 1-ethylbutoxy group, 1 , 3-dimethylbutoxy group, n-pentyloxy group, 5-methylhexyloxy group, 4-methylhexyloxy group, 3-methylhexyloxy group, 2-methylhexyloxy group, 1-methylhexyloxy group, 3- Ethyl pentyloxy group,
2-ethylpentyloxy group, 1-ethylpentyloxy group, 4,4-dimethylpentyloxy group, 3,3-dimethylpentyloxy group, 2,2-dimethylpentyloxy group, 1,1-dimethylpentyloxy group, n-octyloxy group, 6-methylheptyloxy group, 5-methylheptyloxy group, 4-methylheptyloxy group, 3
-Methylheptyloxy group, 2-methylheptyloxy group, 1-methylheptyloxy group, 1-ethylhexyloxy group, 1-propylpentyloxy group, 3-ethylhexyloxy group, 5,5-dimethylhexyloxy group, 4, 4-dimethylhexyloxy group, 2,2-diethylbutoxy group, 3,3-diethylbutoxy group, 1-methyl-1-propylbutoxy group and the like,

The alkoxyalkyl group having 3 to 8 carbon atoms represented by R ¹ is, for example, an ethoxymethyl group,
n-propoxymethyl group, isopropoxymethyl group, se
c-butoxymethyl group, isobutoxymethyl group, (1-
Ethylpropoxy) methyl group, (2-ethylbutoxy)
Methyl group, (1-ethylbutoxy) methyl group, (2-ethylpentyloxy) methyl group, (3-ethylpentyloxy) methyl group, 2-methoxyethyl group, 1-methoxyethyl group, 2-ethoxyethyl group, 3-methoxypropyl group, 2-methoxypropyl group, 1-methoxypropyl group, 2-ethoxypropyl group, 3- (n-propoxy) propyl group, 4-methoxybutyl group, 2-methoxybutyl group, 4-ethoxybutyl group Group, 2-ethoxybutyl group, 5-ethoxypentyl group, 6-ethoxyhexyl group, etc.,

The alkenyl group having 3 to 8 carbon atoms represented by R ¹ is, for example, 1-methylvinyl group, allyl group, 2-methylallyl group, 1-propenyl group, 1-methyl-1-propenyl group. , 2-methyl-1-propenyl group, 1,1-dimethyl-2-propenyl group, 2-butenyl group, 3-butenyl group, 3-methyl-2-butenyl group,
2-methyl-2-butenyl group, 2-methyl-3-butenyl group, 1-pentenyl group, 2-pentenyl group, 1-hexenyl group, 2-hexenyl group, 5-hexenyl group, 6-
A heptenyl group, a 7-octenyl group and the like,

The alkenyloxy group having 3 to 8 carbon atoms represented by R ¹ is, for example, allyloxy group, 2-methylallyloxy group, 1-propenyloxy group, 2-methyl-1-propenyloxy group, 2-butenyloxy group, 3-butenyloxy group, 3-methyl-2-butenyloxy group, 2-methyl-2-butenyloxy group, 2-methyl-3-butenyloxy group, 2-pentenyloxy group, 1-pentenyloxy group, 1 -Hexenyloxy group, 2-hexenyloxy group, 5-hexenyloxy group, 6-heptenyloxy group, 7-octenyloxy group and the like,

The alkenyloxyalkyl group having 3 to 8 carbon atoms represented by R ¹ includes, for example, allyloxymethyl group, (2-methylallyloxy) methyl group and (1
-Propenyloxy) methyl group, (2-methyl-1-propenyloxy) methyl group, (2-butenyloxy) methyl group, (3-butenyloxy) methyl group, (3-methyl-2-butenyloxy) methyl group, (2 -Methyl-2
-Butenyloxy) methyl group, (2-methyl-3-butenyloxy) methyl group, (2-pentenyloxy) methyl group, (1-pentenyloxy) methyl group, (1-hexenyloxy) methyl group, (2-hexenyloxy) ) Methyl group, (5-hexenyloxy) methyl group, (6-heptenyloxy) methyl group, 2-allyloxyethyl group, 2- (2-methylallyloxy) ethyl group, 2-
(1-Propenyloxy) ethyl group, 2- (2-methyl-1-propenyloxy) ethyl group, 2- (2-butenyloxy) ethyl group, 2- (3-butenyloxy) ethyl group, 2- (3-methyl -2-butenyloxy) ethyl group, 2- (2-methyl-2-butenyloxy) ethyl group, 2- (2-methyl-3-butenyloxy) ethyl group, 2- (2-pentenyloxy) ethyl group, 2- ( 1
-Pentenyloxy) ethyl group, 2- (1-hexenyloxy) ethyl group, 2- (2-hexenyloxy) ethyl group, 2- (5-hexenyloxy) ethyl group, 1-allyloxyethyl group, 1- ( 2-methylallyloxy)
Ethyl group, 1- (1-propenyloxy) ethyl group, 1
-(2-methyl-1-propenyloxy) ethyl group, 1
-(2-butenyloxy) ethyl group, 1- (3-butenyloxy) ethyl group, 1- (3-methyl-2-butenyloxy) ethyl group, 1- (2-methyl-2-butenyloxy) ethyl group, 1- ( 2-methyl-3-butenyloxy) ethyl group, 1- (2-pentenyloxy) ethyl group, 1- (1-pentenyloxy) ethyl group, 1- (1
-Hexenyloxy) ethyl group, 1- (2-hexenyloxy) ethyl group, 1- (5-hexenyloxy) ethyl group and the like,

The haloalkyl group having 3 to 8 carbon atoms represented by R ¹ is, for example, 3-fluoropropyl group,
2,2,3,3,3-pentafluoropropyl group, 2-
Chloro-1-methylpropyl group, 3-chloropropyl group, 2-chloropropyl group, 2,3-dichloropropyl group, 3-bromopropyl group, 2-bromopropyl group, 3
-Iodopropyl group, 4-fluorobutyl group, 3,3
4,4,4-pentafluoro-2-butyl group, 4-chlorobutyl group, 3-chlorobutyl group, 2,3,4-trichlorobutyl group, 4-bromobutyl group, 3-bromobutyl group, 4-iodobutyl group, 5 -Fluoropentyl group, 5
-Chloropentyl group, 5-bromopentyl group, 6-fluorohexyl group, 6-chlorohexyl group, 6-bromohexyl group, 7-fluoroheptyl group, 7-bromoheptyl group, 8-fluorooctyl group, 8-bromo Octyl group, etc.,

The haloalkoxy group having 3 to 8 carbon atoms represented by R ¹ includes, for example, 3-fluoropropoxy group, 2,2,3,3,3-pentafluoropropoxy group and 2-chloro-1. -Methylpropoxy group, 3-chloropropoxy group, 2-chloropropoxy group, 2,3-dichloropropoxy group, 3-bromopropoxy group, 2-bromopropoxy group, 3-iodopropoxy group, 4-fluorobutoxy group, 3 , 3,4,4,4-pentafluoro-
2-butoxy group, 4-chlorobutoxy group, 3-chlorobutoxy group, 2,3,4-trichlorobutoxy group, 4-bromobutoxy group, 3-bromobutoxy group, 4-iodobutoxy group, 5-fluoropentyloxy group Group, 5-chloropentyloxy group, 5-bromopentyloxy group, 6-
A fluorohexyloxy group, a 6-chlorohexyloxy group, a 6-bromohexyloxy group, a 7-fluoroheptyloxy group, a 7-bromoheptyloxy group, an 8-fluorooctyloxy group, an 8-bromooctyloxy group and the like,

The haloalkoxyalkyl group having 3 to 8 carbon atoms represented by R ¹ is, for example, (3-fluoropropoxy) methyl group or (2,2,3,3,3-pentafluoropropoxy). Methyl group, (2-chloro-1-methylpropoxy) methyl group, (3-chloropropoxy)
Methyl group, (2-chloropropoxy) methyl group, (2,
3-dichloropropoxy) methyl group, (3-bromopropoxy) methyl group, (2-bromopropoxy) methyl group, (3-iodopropoxy) methyl group, (4-fluorobutoxy) methyl group, (3,3,4 , 4,4-pentafluoro-2-butoxy) methyl group, (4-chlorobutoxy) methyl group, (3-chlorobutoxy) methyl group,
(2,3,4-trichlorobutoxy) methyl group, (4-
(Bromobutoxy) methyl group, (3-bromobutoxy) methyl group, (4-iodobutoxy) methyl group, (5-fluoropentyloxy) methyl group, (5-chloropentyloxy) methyl group, (5-bromopentyloxy) ) Methyl group, (6-fluorohexyloxy) methyl group, (6
-Chlorohexyloxy) methyl group, (6-bromohexyloxy) methyl group, (7-fluoroheptyloxy) methyl group, (7-bromoheptyloxy) methyl group, 1- (3-fluoropropoxy) ethyl group, 1 −
(2,2,3,3,3-pentafluoropropoxy) ethyl group, 1- (2-chloro-1-methylpropoxy) ethyl group, 1- (3-chloropropoxy) ethyl group, 1-
(2-chloropropoxy) ethyl group, 1- (2,3-dichloropropoxy) ethyl group, 1- (3-bromopropoxy) ethyl group, 1- (2-bromopropoxy) ethyl group, 1- (3-iodo Propoxy) ethyl group, 1- (4
-Fluorobutoxy) ethyl group, 1- (3,3,4,
4,4-pentafluoro-2-butoxy) ethyl group, 1
-(4-chlorobutoxy) ethyl group, 1- (3-chlorobutoxy) ethyl group, 1- (2,3,4-trichlorobutoxy) ethyl group, 1- (4-bromobutoxy) ethyl group, 1- ( 3-bromobutoxy) ethyl group, 1- (4-
Iodobutoxy) ethyl group, 1- (5-fluoropentyloxy) ethyl group, 1- (5-chloropentyloxy) ethyl group, 1- (5-bromopentyloxy) ethyl group, 1- (6-fluorohexyloxy) ) Ethyl group,
1- (6-chlorohexyloxy) ethyl group, 1- (6
-Bromohexyloxy) ethyl group, 2- (3-fluoropropoxy) ethyl group, 2- (2,2,3,3,3-
Pentafluoropropoxy) ethyl group, 2- (2-chloro-1-methylpropoxy) ethyl group, 2- (3-chloropropoxy) ethyl group, 2- (2-chloropropoxy) ethyl group, 2- (2,3 -Dichloropropoxy) ethyl group, 2- (3-bromopropoxy) ethyl group, 2-
(2-Bromopropoxy) ethyl group, 2- (3-iodopropoxy) ethyl group, 2- (4-fluorobutoxy)
Ethyl group, 2- (3,3,4,4,4-pentafluoro-2-butoxy) ethyl group, 2- (4-chlorobutoxy) ethyl group, 2- (3-chlorobutoxy) ethyl group,
2- (2,3,4-trichlorobutoxy) ethyl group, 2
-(4-bromobutoxy) ethyl group, 2- (3-bromobutoxy) ethyl group, 2- (4-iodobutoxy) ethyl group, 2- (5-fluoropentyloxy) ethyl group,
2- (5-chloropentyloxy) ethyl group, 2- (5
-Bromopentyloxy) ethyl group, 2- (6-fluorohexyloxy) ethyl group, 2- (6-chlorohexyloxy) ethyl group, 2- (6-bromohexyloxy) ethyl group, and the like,

The haloalkenyl group having 3 to 8 carbon atoms represented by R ¹ includes, for example, 2,3-dichloroallyl group, 2,3-dibromoallyl group, 2-chloro-2-propenyl group and 3- Chloro-2-propenyl group, 2-bromo-2-propenyl group, 2-chloromethyl-2-propenyl group, 2-chloro-3-butenyl group, 3-chloro-2-
A butenyl group, a 4-chloro-2-butenyl group, a 4-bromo-2-butenyl group, a 7-chloro-7-octenyl group, and the like,

The haloalkenyloxy group having 3 to 8 carbon atoms represented by R ¹ is, for example, 2,3-dichloroallyloxy group, 2,3-dibromoallyloxy group, 2-
Chloro-2-propenyloxy group, 3-chloro-2-propenyloxy group, 2-bromo-2-propenyloxy group, 2-chloro-3-butenyloxy group, 3-chloro-
A 2-butenyloxy group, a 4-chloro-2-butenyloxy group, a 4-bromo-2-butenyloxy group, a 7-chloro-7-octenyloxy group, and the like,

The haloalkenyloxyalkyl group having 3 to 8 carbon atoms represented by R ¹ is, for example, (2,3
-Dichloroallyloxy) methyl group, (2,3-dibromoallyloxy) methyl group, (2-chloro-2-propenyloxy) methyl group, (3-chloro-2-propenyloxy) methyl group, (2- Bromo-2-propenyloxy) methyl group, (2-chloro-3-butenyloxy) methyl group, (3-chloro-2-butenyloxy) methyl group, (4-chloro-2-butenyloxy) methyl group,
(4-Bromo-2-butenyloxy) methyl group, (7-
Chloro-7-octenyloxy) methyl group, 1- (2,
3-dichloroallyloxy) ethyl group, 1- (2,3-
Dibromoallyloxy) ethyl group, 1- (2-chloro-
2-propenyloxy) ethyl group, 1- (3-chloro-
2-propenyloxy) ethyl group, 1- (2-bromo-
2-propenyloxy) ethyl group, 1- (2-chloro-
3-butenyloxy) ethyl group, 1- (3-chloro-2)
-Butenyloxy) ethyl group, 1- (4-chloro-2-
Butenyloxy) ethyl group, 1- (4-bromo-2-butenyloxy) ethyl group, 1- (7-chloro-7-octenyloxy) ethyl group, 2- (2,3-dichloroallyloxy) ethyl group, 2 -(2,3-Dibromoallyloxy) ethyl group, 2- (2-chloro-2-propenyloxy) ethyl group, 2- (3-chloro-2-propenyloxy) ethyl group, 2- (2-bromo -2-propenyloxy) ethyl group, 2- (2-chloro-3-butenyloxy) ethyl group, 2- (3-chloro-2-butenyloxy) ethyl group, 2- (4-chloro-2-butenyloxy) ethyl group , 2- (4-bromo-2-butenyloxy) ethyl group, 2- (7-chloro-7-octenyloxy) ethyl group, and the like,

The alkynyloxy group having 3 to 8 carbon atoms represented by R ¹ is, for example, 2-propynyloxy group, 1-methyl-2-propynyloxy group, 1-ethyl-2-propynyloxy group, 1-propyl-2-propynyloxy group, 2-butynyloxy group, 1-ethyl-2
-Butynyloxy group, 1-propyl-2-butynyloxy group, 1-n-butyl-2-butynyloxy group, 2-pentynyloxy group, 4-methyl-2-pentynyloxy group, 1,4-dimethyl-2- Pentynyloxy group, 1-
An ethyl-4-methyl-2-pentynyloxy group, a 2-hexynyloxy group, a 3-hexynyloxy group, a 2-heptynyloxy group, a 2-octynyloxy group, a 7-octynyloxy group and the like,

The halogen atom represented by R ² is, for example, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or the like, preferably a chlorine atom.

The halogen atom represented by R ³ is, for example, a fluorine atom, a chlorine atom, a bromine atom or an iodine atom,

The alkyl group having 1 to 4 carbon atoms represented by R ⁵ is, for example, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, isobutyl group, A tert-butyl group and the like, preferably an ethyl atom.

The haloalkyl group having 1 to 4 carbon atoms represented by R ⁵ is, for example, trifluoromethyl group, difluoromethyl group, 2-fluoroethyl group, 1-fluoroethyl group, 1,2-difluoroethyl group. , 2,2,2-trifluoroethyl group, 2-chloroethyl group, 3-fluoropropyl group, 2-fluoropropyl group, 1-fluoropropyl group, 3-chloropropyl group, 3-bromopropyl group, 4-fluoro A butyl group, a 4-chlorobutyl group, etc.,

The alkoxy group having 1 to 4 carbon atoms represented by R ⁵ includes, for example, methoxy group, ethoxy group, propoxy group, isopropoxy group, n-butoxy group, tert-
A butoxy group, an isobutoxy group, a sec-butoxy group, etc.,

The haloalkoxy group having 1 to 4 carbon atoms represented by R ⁵ is, for example, a trifluoromethoxy group,
Difluoromethoxy group, 2-fluoroethoxy group, 2,
2,2-trifluoroethoxy group, 1-fluoroethoxy group, 1,2-difluoroethoxy group, 3-fluoropropoxy group, 1-fluoropropoxy group, 2-fluoropropoxy group, 4-fluorobutoxy group, 2-chloro Ethoxy group, 3-chloropropoxy group, 4-chlorobutoxy group, 3-bromopropoxy group, 1,1,2,2-tetrafluoroethoxy group, 1,1-difluoromethoxy group and the like,

The alkylthio group having 1 to 4 carbon atoms represented by R ⁵ includes, for example, methylthio group, ethylthio group, n-propylthio group, isopropylthio group, n-butylthio group, isobutylthio group, sec-butylthio group. Base,
a tert-butylthio group or the like,

The haloalkylthio group having 1 to 4 carbon atoms represented by R ⁵ is, for example, difluoromethylthio group, trifluoromethylthio group, 2-fluoroethylthio group, 1-fluoroethylthio group, 2-chloro. Ethylthio group, 1,2-difluoroethylthio group, 2,2,2-
Trifluoroethylthio group, 3-fluoropropylthio group, 2-fluoropropylthio group, 1-fluoropropylthio group, 3-chloropropylthio group, 3-bromopropylthio group, 4-fluorobutylthio group, 4- A chlorobutylthio group and the like.

The substitution position of R ⁵ is preferably 4-position.

The compound of the present invention represented by the general formula:
For example, it can be manufactured by the following method.

(Production Method A) General Formula 7

[0032]

[Chemical 7]

[In the formula, M represents an alkali metal atom or a hydrogen atom, and R ¹ , R ² , R ³ and m have the same meanings as described above. ] A phenolic compound represented by the general formula
Conversion 8

[0034]

[Chemical 8]

[Wherein A represents a halogen atom, R ⁴ ,
R ⁵ and n have the same meanings as described above. ] It can manufacture by making it react with the compound shown by these.

The above reaction is preferably carried out in the presence of a suitable base in an inert solvent. However, when M is an alkali metal atom, the presence of a base is not always necessary.

Examples of usable bases include caustic alkalis such as caustic potash, alkali carbonates such as potassium carbonate,
Examples thereof include alkali metals such as sodium metal, hydrides of alkali metals such as sodium hydride, and organic bases such as sodium methoxide, sodium ethoxide, triethylamine and pyridine. Also, if necessary,
A catalyst such as an ammonium salt (eg, triethylbenzylammonium chloride) may be added to the reaction system.

Examples of usable solvents include lower alcohols such as ethanol, propanol, isopropanol and tertiary butyl alcohol, ketones such as acetone and methyl ethyl ketone, hydrocarbons such as benzene and toluene, diethyl ether and isopropyl ether. Ethers such as tetrahydrofuran and dioxane, N, N-
Amides such as dimethylformamide and hexamethylphosphoric triamide, dichloromethane, chloroform,
Examples thereof include halogenated hydrocarbons such as 1,2-dichloroethane and chlorobenzene, acetonitrile, nitromethane and water. If necessary, a mixed solvent of these solvents can also be used.

The reaction temperature may be in the range of -20 ° C to the boiling point of the solvent used in the reaction, but is -5 ° C.
The range from to the boiling point of the solvent used in the reaction is more desirable.

The molar ratio of the raw material and the base to be used in the reaction can be set arbitrarily, but it is advantageous to carry out the reaction in an equimolar ratio or a ratio close thereto.

The reaction solution after completion of the reaction can be subjected to usual post-treatments such as extraction with an organic solvent and concentration to obtain the desired compound of the present invention. If necessary, it can be purified by usual operations such as chromatography, distillation and recrystallization.

(Production Method B) General Formula 9

[0043]

[Chemical 9]

[In the formula, R ¹ , R ² , R ³ and m have the same meanings as described above. ] The phenolic compound represented by

[0045]

[Chemical 10]

[In the formula, R ⁴ , R ⁵ and n have the same meanings as described above. ] It can manufacture by making it react with the alcoholic compound shown by these.

The above reaction is particularly advantageous when R ³ is not a hydrogen atom, and the reaction is preferably carried out in the presence of a suitable dehydrating catalyst or dehydrating agent, if necessary, in an inert solvent.

Examples of the dehydration catalyst to be used include inorganic acids such as hydrochloric acid and sulfuric acid, aromatic sulfonic acids or sulfonic acid chlorides, and examples of the dehydrating agent include dicyclohexylcarbodiimide and diisopropyl azocarboxylate. Triphenylphosphine,
Alternatively, diethyl azodicarboxylate and triphenylphosphine may be used.

Examples of usable solvents include hydrocarbons such as benzene and toluene, and halogenated hydrocarbons such as carbon tetrachloride and dichloromethane.

The reaction temperature can range from -20 ° C to 200 ° C or the boiling point of the solvent used.

The molar ratio of the raw material and the dehydrating agent to be used in the reaction can be set arbitrarily, but it is advantageous to carry out the reaction in an equimolar ratio or a ratio close thereto.

The reaction solution after completion of the reaction can be subjected to usual post-treatments such as extraction with an organic solvent and concentration to obtain the desired compound of the present invention. If necessary, it can be purified by usual operations such as chromatography, distillation and recrystallization.

Further, in the compounds of the present invention, in the case of compounds having an asymmetric carbon atom, the compounds of the present invention include optically active isomers having biological activity and mixtures thereof in any ratio.

Among the phenolic compounds represented by the general formula (7), which are the starting materials for the compound of the present invention, the phenolic compound in which M represents an alkali metal atom is derived from the phenolic compound represented by the general formula (9) and synthesized. be able to. As the phenolic compound represented by the general formula 9, a commercially available one can be used, or can be easily synthesized from a commercially available one by a usual method. Further, among the phenolic compounds represented by the general formula 7 or 9, those in which R ² represents a chlorine atom are disclosed in, for example, J. Amer. Chem. Soc., 73 , 2723 (1951), J. Or.
It can also be synthesized according to the method described in g. Chem., 39 , 1160 (1974) or the like. Further, among the phenolic compounds represented by the general formula 9, compounds in which R ² represents a chlorine atom are represented by the general formula 11

[0055]

[Chemical 11]

[In the formula, R ¹ , R ³ and m have the same meanings as described above. ] A phenolic compound represented by the general formula 9 in which R ² is a chlorine atom is obtained by reacting a phenolic compound represented by the following with a chlorinating agent in the presence of a solvent according to a usual method. You can also

As the chlorinating agent in the above reaction formula, chlorine, t-butyl hypochlorite, sulfuryl chloride or the like can be used. If necessary, a solvent can be used, and examples of the solvent that can be used include dichloromethane, dichloroethane, carbon tetrachloride, benzene, acetic acid and the like. It goes without saying that the solvent used here is properly used according to the type of chlorinating agent. The reaction temperature may range from −78 ° C. to the boiling point of the solvent or chlorinating agent (sulfuryl chloride etc.) used in the reaction, but from −20 ° C. to the solvent or chlorinating agent (sulfuryl chloride) used in the reaction. Etc.) up to the boiling point range is desirable.
The molar ratio of the raw material and the chlorinating agent to be used for the reaction can be set arbitrarily, but it is advantageous to carry out the reaction at an equimolar ratio or a ratio close thereto. The reaction solution after completion of the reaction can be subjected to usual post-treatments such as extraction with an organic solvent and concentration to obtain the target compound. If necessary, it can be purified by usual operations such as chromatography, distillation and recrystallization.

The compound represented by the general formula (8) or (10), which is a raw material of the compound of the present invention, is a commercially available compound, or can be easily synthesized from a commercially available compound by a conventional method. it can.

The compounds of the present invention which can be produced according to these production methods are shown in Tables 1 to 23. However, these compounds are merely examples, and the present invention is not limited thereto.

[0060]

[Table 1]

[0061]

[Table 2]

[0062]

[Table 3]

[0063]

[Table 4]

[0064]

[Table 5]

[0065]

[Table 6]

[0066]

[Table 7]

[0067]

[Table 8]

[0068]

[Table 9]

[0069]

[Table 10]

[0070]

[Table 11]

[0071]

[Table 12]

[0072]

[Table 13]

[0073]

[Table 14]

[0074]

[Table 15]

[0075]

[Table 16]

[0076]

[Table 17]

[0077]

[Table 18]

[0078]

[Table 19]

[0079]

[Table 20]

[0080]

[Table 21]

[0081]

[Table 22]

[0082]

[Table 23]

Examples of pests on which the compound of the present invention exerts its effects include the following.

Hemiptera pests Planthoppers such as the brown planthopper, scorpion planthopper, and brown planthopper, leafhopper leafhoppers, leafhopper leafhoppers, leafhopper leafhoppers, leafhopper leafhoppers, leafhopper leafhoppers such as leafhopper leafhoppers, leafhopper leafhoppers, leafhoppers, leafhoppers Aphids such as aphids, stink bugs, whiteflies of tobacco, whiteflies such as whitefly whitefly, scale insects, gum beetles, psyllids, etc.

Lepidopteran pests Nikameiga (Nikameichu), Kobusumemaiga, Nostume suga, etc., Spodoptera litura, Spodoptera litura, Spodoptera litura, such as Pieris rapae, Squid moth, etc.
Agrothis spp., Heliothis spp. ( Heliothis spp.) Such as leaf moths, hornworms, leaf moths, hemlock moths, hemlock moths, mosquitoes, cabbage moths and tamanaga moths
p.), diamondback moth, moth, moth, etc.

Diptera Pests Culex pipiens, Culex pipiens and other mosquitoes, Aedes aegypti such as Aedes aegypti and Aedes albopictus, Anopheles mosquitoes such as Aedes albopictus, Musca mosquitoes, Musca domestica, Musca domestica, Musca domestica, Musca domestica, Musca domestica, Musca domestica, Musca domestica, Musca domestica, Musca domestica, Musca domestica, Musca domestica, Musca domestica, Musca domestica, Musca domestica, Musca domestica, Musca domestica, Musca domestica, Musca domestica, flesh fly, flesh fly Drosophila, such as onion flies, gall midges, fruit flies, fruit flies, fruit flies,
Butterfly flies, flies, gnats, sand flies, etc.

Coleoptera pests Western corn rootworms, Southern corn rootworms and other corn rootworms, Rana buoy buoy, Scarabaeidae such as Himekonega, Weevil weevils, Weevil weevils, Weevil such as Azuki bean weevils, Beetle worms, etc. Epiracuna genus such as beetle beetle, beetle beetle, beetle beetle, beetle beetle, stag beetle, etc.
( Epilach-na spp.), Flat beetle, long beetle, long beetle, etc.

Pests of the order Lepidoptera, German cockroaches, Black cockroaches, American cockroaches, Black cockroaches, Cockroaches, etc.

Pests of the order Thysanoptera, Thrips palmi, Chanomidria thrips, Thrips thrips, etc.

Hymenoptera pests Ants, wasps such as turnips, etc.

Orthoptera pests such as moss, grasshopper, etc.

Insect insect pest Human flea etc.

Lice pests Human lice, lice, etc.

Isopterous pests Effective against Yamato termites, house termites and the like. Further, among them, it is more suitable for the control of hemiptera pests, and particularly, it shows a superior effect against planthoppers and leafhoppers or aphids that damage rice crops, and exhibits an excellent control effect.

By adding other insecticides and / or acaricides, the pest control of the compound of the present invention can be applied practically to various kinds of pests and various use situations. Suitable additives include, for example, fenitrothion [O, O-dimethyl O- (3-methyl-4-nitrophenyl) phosphorothioate], phenthion [O, O-dimethyl O- [3-methyl-4- (methylthio) phenyl]. Phosphorothioate], diazinone [2-isopropyl-4-methylpyrimidyl-6) -diethylphosphorothioate], chlorpyrifos [O, O
-Diethyl-O-3,5,6-trichloro-2-pyridylphosphorothioate], acephate [O, S-dimethyl-acetophosphoramidothioate], methidathion [S-2,3-dihydro-5-methoxy-2-] Oxo-
1,3,4-thiadiazol-3-ylmethyl O, O-
Dimethyl phosphorodithioate], ethyl thiomethone [O, O-diethyl S-2-ethylthioethyl phosphorodithioate], DDVP [2,2-dichlorovinyl dimethyl phosphate], sulprophos [O-ethyl
O-4- (methylthio) phenyl S-propyl phosphorodithioate], dianophos [O-4-cyanophenyl O, O-dimethylphosphorothioate], salicione [2-methoxy-4H-1,3,2-benzodioxa] Phosphorin-2-sulfide], dimethoate [O, O
-Dimethyl-S- (N-methylcarbamoylmethyl) dithiophosphate], fentoate [ethyl 2-dimethoxyphosphinothioylthio (phenyl) acetate], malathion [diethyl (dimethoxyphosphinothioylthio) succinate], trichlorfon [dimethyl] 2,2,2-Trichloro-1-hydroxyethylphosphonate], azinephosmethyl [S-3,4-dihydro-4-oxo-1,2,3-benzotriazine-3-
Ilmethyl O, O-dimethyl phosphorodithioate], monocrotophos [dimethyl (E) -1-methyl-
2- (methylcarbamoyl) vinyl phosphate] and the like,

BPMC [2-sec-butylphenylmethylcarbamate], benflacarb [ethyl N-
[2,3-Dihydro-2,2-dimethylbenzofuran-
7-yloxycarbonyl (methyl) aminothio] -N
-Isopropyl-β-alaninate], propoxur [2-isopropoxyphenyl N-methylcarbamate], carbosulfan [2,3-dihydro-2,2-
Dimethyl-7-benzo [b] furanyl N-dibutylaminothio-N-methylcarbamate], carbaryl [1
-Naphthyl-N-methylcarbamate], mesomel [S
-Methyl-N-[(methylcarbamoyl) oxy] thioacetimidate], ethiophencarb [2- (ethylthiomethyl) phenylmethylcarbamate], aldicarb [2-methyl-2- (methylthio) propionaldehyde O-methylcarbamoyloxy ], Carbamate compounds such as oxamyl [N, N-dimethyl-2-methylcarbamoyloxyimino-2- (methylthio) acetamide],

Etofenprox [2- (4-ethoxyphenyl) -2-methylpropyl-3-phenoxybenzyl ether], fenvalerate [(RS) -α-
Cyano-3-phenoxybenzyl (RS) -2- (4-
Chlorophenyl) -3-methylbutyrate], esfenvalerate [(S) -α-cyano-3-phenoxybenzyl (S) -2- (4-chlorophenyl) -3-methylbutyrate], fenpropatorin [( RS) -α-
Cyano-3-phenoxybenzyl 2,2,3,3-tetramethylcyclopropanecarboxylate], cypermethrin [(RS) -α-cyano-3-phenoxybenzyl (1RS, 3RS)-(1RS, 3RS) -3 −
(2,2-Dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate], permethrin [3-phenoxybenzyl (1RS, 3RS)-(1RS, 3R
S) -3- (2,2-Dichlorovinyl) -2,2-methylcyclopropane-carboxylate], cyhalothrin [(RS) -α-cyano-3-phenoxybenzyl (Z)-(1RS, 3RS)- 3- (2-chloro-3,
3,3-trifluoropropenyl) -2,2-dimethylcyclopropanecarboxylate], deltamethrin [(S) -α-cyano-m-phenoxybenzyl (1
R, 3R) -3 (2,2-dibromovinyl) -2-dimethylcyclopropanecarboxylate], cycloprothrin [(RS) -α-cyano-3-phenoxybenzyl (RS) -2,2-dichloro-] 1- (4-ethoxyphenyl) cyclopropanecarboxylate] and the like,

Thiadiazine derivatives such as buprofezin [2-tert-butylimino-3-isopropyl-5-phenyl-1,3,5-triadiazin-4-one], imidacloprid [1- (6-chloro-3-pyridyl] Methyl) -N-nitro-imidazolidine-2-ylideneamine] and the like, nitroimidazolidine derivatives, cartap [S, S '-(2-dimethylaminotrimethylene) bis (thiocarbamate)], thiocyclam [N, N-dimethyl-1] , 2,3-Trithian-5-ylamine], Bensultap [S, S′-2-dimethylaminotrimethylene di (benzenethiosulfonate)], and other nereistoxin derivatives, endosulfan [6,7,8,
9,10,10-hexachloro-1,5,5a, 6
9,9a-hexahydro-6,9-methano-2,4,3
-Benzodioxathiepine oxide], γ-BHC
Chlorinated hydrocarbon compounds such as [1,2,3,4,5,6-hexachlorocyclohexane], chlorfluablone [1- [3,5-dichloro-4- (3-chloro-5-trifluoromethylpyridine) -2-yloxy) phenyl] -3- (2,6-difluorobenzoyl) urea], teflubenzuron [1- (3,5-dichloro-
2,4-difluorophenyl) -3- (2,6-difluorobenzoyl) urea], flufenoxuron [1-
Benzoylphenylurea compounds such as [4- (2-chloro-4-trifluoromethylphenoxy) -2- (fluorophenyl] -3- (2,6-difluorobenzoyl) urea], amitraz [N, N ′ [ Formamidine derivatives such as (methylimino) dimethylidene] di-2,4-xylidine], chlordimeform [N ′-(4-chloro-2-methylphenyl) -N, N-dimethylmethanimidamide] and the like can be mentioned.

When the compound of the present invention is used as an active ingredient of a pest control agent, it may be used as it is without adding any component of the book, but it is usually a solid carrier, a liquid carrier, a gaseous carrier or a bait. Etc., and if necessary, add surfactants and other auxiliaries for formulation, oils, emulsions, wettable powders, flowable agents such as water-suspending agents / emulsifiers, granules, powders,
It is used as a formulation for aerosol, self-combustion type smoke agent / chemical reaction type smoke agent / heated smoke agent such as porous ceramic plate smoke agent, ULV agent and poison bait.

These formulations usually contain the compound of the present invention as an active ingredient in an amount of 0.001% to 95% by weight.
Examples of solid carriers used for formulation include clays (kaolin clay, diatomaceous earth, synthetic hydrous silicon oxide, bentonite, fubasami clay, acid clay, etc.), talc, ceramics, and other inorganic minerals (sericite, quartz, Sulfur, activated carbon, calcium carbonate, hydrated silica, etc.),
Examples thereof include fine powders or granules of chemical fertilizers (ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, ammonium salt, etc.), and examples of liquid carriers include water, alcohols (methanol, ethanol, etc.), ketones (acetone, Methyl ethyl ketone, etc.),
Aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, methylnaphthalene, etc.), aliphatic hydrocarbons (hexane, cyclohexane, kerosene, light oil, etc.), esters (ethyl acetate, butyl acetate, etc.), nitriles (acetonitrile) , Isobutyronitrile, etc.), ethers (diisopropyl ether, dioxane, etc.), acid amides (N, N-dimethylformamide, N, N-dimethylacetamide, etc.), halogenated hydrocarbons (dichloromethane, trichloroethane, tetrachloride) Carbon, etc.), dimethyl sulfoxide, soybean oil, vegetable oil such as cottonseed oil, etc.,
Examples of the gaseous carrier, that is, the propellant include CFC gas, butane gas, LPG (liquefied petroleum gas), dimethyl ether, carbon dioxide gas and the like.

Examples of the surfactant include alkyl sulfates, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers and polyoxyethylenated products thereof, polyethylene glycol ethers, polyhydric alcohol esters, sugar alcohols. Examples include derivatives.

Examples of auxiliaries for formulation such as a fixing agent and a dispersant include casein, gelatin, polysaccharides (starch powder, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, saccharides, synthetic water-soluble polymers. (Polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylic acid, etc.) and the like, and examples of the stabilizer include PAP (isopropyl acid phosphate) and BH.
T (2,6-di-tert-butyl-4-methylphenol), BHA (mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol), vegetable oil, mineral oil , Surfactants, fatty acids or esters thereof, and the like.

Examples of the base material of the self-burning smoke agent include nitrate, nitrite, guanidine salt, potassium chlorate,
Combustion exothermic agent such as nitrocellulose, ethylcellulose, wood powder, alkali metal salt, alkaline earth metal salt, pyrolysis stimulant such as dichromate, chromate, oxygen supply agent such as potassium nitrate, melamine, wheat starch Examples include a combustion-supporting agent, an extender such as diatomaceous earth, and a binder such as a synthetic paste. As the base material of the chemical reaction type smoke agent, for example, alkali metal sulfide, polysulfide, hydrosulfide, hydrous salt,
Exothermic agents such as calcium oxide, carbonaceous materials, iron carbide, catalysts such as activated clay, azodicarbonamide, benzenesulfonyl hydrazide, dinitrosopentamethylenetetramine, organic foaming agents such as polystyrene and polyurethane, natural fiber pieces, synthetic fibers Examples include fillers such as pieces.

Examples of base materials for poison baits include bait ingredients such as grain flour, vegetable essential oils, sugars and crystalline cellulose, antioxidants such as dibutylhydroxytoluene and nordihydroguaiaretic acid, preservatives such as dehydroacetic acid, and capsicum. Examples include edible foods such as powdered foods, cheese flavor, and onion flavor.

Formulations of flowable agents (suspension in water or emulsions in water) generally contain 1 to 75% of the compound in an amount of 0.5 to 15%.
% Dispersant, 0.1-10% suspension aid (eg, protective colloid or compound that imparts thixotropic properties), 0-
Finely dispersed in water containing 10% of suitable auxiliaries (eg defoaming agent, rust preventive, stabilizer, spreading agent, penetration aid, antifreeze agent, antibacterial agent, anti-smudge agent, etc.) It is obtained by It is also possible to use an oil in which the compound is hardly dissolved in place of water to prepare a suspension in oil. Examples of the protective colony include gelatin, casein, gums, cellulose ether, polyvinyl alcohol and the like. Examples of the compound that imparts thixotropy include bentonite, aluminum magnesium silicate, xanthan gum, polyacrylic acid, and the like.

The thus obtained preparation is used as it is or after diluted with water or the like. Also other pesticides,
It can be used simultaneously with or without mixing with nematicides, acaricides, fungicides, herbicides, plant growth regulators, synergists, fertilizers, soil improvers, animal feeds and the like.

When the compound of the present invention is used as an agricultural pest control agent, its application amount is usually 0.1 g to 500 g per 10 ares, and emulsions, wettable powders, flowable agents, etc. are diluted with water. When used, the application concentration is usually 0.0001 ppm to 1000 ppm, and granules, powders, etc. are applied as they are without any dilution. When used as a pest control agent for epidemics, emulsions, wettable powders, flowable agents, etc., are usually 0.0001 ppm to 10,000 ppm in water.
Apply it after diluting it to oil, aerosol, smoke agent, ULV
Apply the drug and poison bait as they are.

The application amount and application concentration depend on the kind of formulation, application time, application place, application method, type of pest, degree of damage, etc., and increase without regard to the above range, It can be reduced.

[0109]

EXAMPLES The present invention will be described in more detail below with reference to production examples, formulation examples and test examples, but the present invention is not limited to these examples. First, production examples of the compound of the present invention will be shown.

Production Example 1 Production Method of Compound (2) by (Production Method A) 0.30 g of potassium carbonate, 0.40 g of 2-chloro-4-sec-butoxyphenol, p-methylbenzyl chloride
A mixture of 0.28 g and 15 ml N, N-dimethylformamide was stirred at room temperature overnight. After adding the reaction solution to ice water,
It was extracted twice with 100 ml of diethyl ether. The ether layers were combined, washed with water, dried and concentrated to give a crude product. The crude product was chromatographed on silica gel with 1-se
0.50 g of c-butoxy-3-chloro-4- (4-methylbenzyloxy) benzene was obtained. Yield 82% n _D ^18.9 1.5557

Production Example 2 Production Method of Compound (1) by (Production Method B) 2-chloro-4-sec-butoxyphenol 0.74 g,
p-Ethylbenzyl alcohol 0.50g, triphenylphosphine 1.00g, diethyl azodicarboxylate
A mixture of 0.65 g and 100 ml of tetrahydrofuran was stirred at room temperature for 48 hours. The reaction solution was concentrated, 50 ml of diethyl ether was added, and the precipitate was filtered. The filtrate is concentrated and then subjected to silica gel chromatography, 1-se
0.71 g of c-butoxy-3-chloro-4- (4-ethylbenzyloxy) benzene was obtained. Yield 60% n _D ^22.6 1.5529

Next, Tables 24 and 25 show some of the compounds of the present invention obtained according to these production methods.

[0113]

[Table 24]

[0114]

[Table 25]

Next, an example of producing an intermediate will be shown. Intermediate Production Example (Production Method of 4-sec-Butoxy-2-chlorophenol) 4-sec-Butoxyphenol (5.0 g) was added to carbon tetrachloride.
Dissolve in 50 ml and stir vigorously below -10 ° C.
3.27 g of t-butyl hypochlorite was slowly added dropwise. After completion of dropping, the mixture was stirred at room temperature. After 5 hours, the reaction mixture was concentrated, 200 ml of ethyl acetate was added to the residue, and the mixture was washed with 5% aqueous sodium bicarbonate solution. After drying and concentrating the ethyl acetate solution, the residue was subjected to silica gel chromatography, and 2-chloro-
5.32 g of 4-sec-butoxy) phenol was obtained. Yield 88% n _D ^23.5 1.5312 Next, Table 26 shows some of the intermediates of the compound of the present invention obtained according to these production methods.

[0116]

[Table 26]

Next, formulation examples are shown. The parts are parts by weight, and the compounds of the present invention are represented by the compound numbers shown in Tables 24 and 25.

Formulation Example 1 Emulsion 10 parts of each of the compounds (1) to (10) of the present invention were dissolved in 35 parts of xylene and 35 parts of dimethylformamide, and polyoxyethylene styryl phenyl ether 14 was added thereto.
Parts and 6 parts of calcium dodecylbenzene sulfonate are added and well mixed with stirring to obtain 10% emulsions of each.

Formulation Example 2 Wettable Powder 20 parts of each of the compounds (1) to (10) of the present invention, 4 parts of sodium lauryl sulfate and 2 parts of calcium lignin sulfonate are prepared.
Part, 20 parts of synthetic hydrous silicon oxide fine powder and 54 parts of silicon earth are added to the mixture and mixed by stirring with a juice mixer to obtain a 20% wettable powder.

Formulation Example 3 Granules To 5 parts of each of the compounds (1) to (10) of the present invention, 5 parts of sodium dodecylbenzenesulfonate, 30 parts of bentonite and 60 parts of clay are added, and they are sufficiently stirred and mixed. Then
An appropriate amount of water is added to these mixtures, the mixture is further stirred, granulated by a granulator, and dried by ventilation to obtain 5% granules.

Formulation Example 4 Dust formulation 0.3 parts of each of the compounds (1) to (10) of the present invention, 1 part of synthetic hydrous silicon oxide fine powder, trade name Dorilleth B as a flocculant
After thoroughly mixing 1 part (manufactured by Sankyo Co., Ltd.) and 7.7 parts of clay in a mortar, stir and mix with a juice mixer. 90 parts of cut clay is added to the obtained mixture and mixed in a bag to obtain each powder.

Formulation Example 5 Powders 0.3 parts of each of the compounds (1) to (10) of the present invention, 2 parts of fenitrothion as an organic phosphorus compound, 3 parts of synthetic silicon oxide hydroxide fine powder, trade name Doloreth B (as an aggregating agent) 1 part of Sankyosha Co., Ltd.) and 3.7 parts of clay are thoroughly mixed in a mortar and then mixed by stirring with a juice mixer. 90 parts of cut clay was added to the obtained mixture and mixed in a bag to obtain each powder.

Formulation Example 6 Powder 0.3 parts of each of the compounds (1) to (10) of the present invention, 2 parts of BPMC (O-sec-butylphenyl N-methylcarbamate) as a carbamate compound, synthetic hydrous silicon oxide fine powder 3 parts, 1 part of trade name Dorilles B (manufactured by Sankyosha Co., Ltd.) as a flocculant, and 3.7 parts of clay are mixed well in a mortar and then mixed with stirring with a juice mixer. 90 parts of cut clay was added to the obtained mixture and mixed in a bag to obtain each powder.

Formulation Example 7 Flowable Agent 10 parts of each of the compounds (1) to (10) of the present invention is added to 40 parts of an aqueous solution containing 6 parts of polyvinyl alcohol, and the mixture is stirred with a mixer to obtain a dispersant. In this, xanthan gum
0.05 parts and aluminum magnesium silicate 0.1
40 parts of an aqueous solution containing 10 parts of propylene glycol, 10 parts of propylene glycol were added, and the mixture was gently stirred and mixed to obtain 10 parts of
% To give an emulsifier in water.

Formulation Example 8 Oil formulation 0.1 part of each of the compounds (1) to (10) of the present invention was mixed with 5 parts of xylene.
Parts and 5 parts of trichloroethane are dissolved and mixed with 89.9 parts of deodorized kerosene to obtain a 0.1% oil solution.

Formulation Example 9 Oily Aerosol Mixture of 0.1 part of each of the compounds (1) to (10) of the present invention, 0.2 part of tetramethrin, 0.1 part of d-phenothrin, 10 parts of trichloroethane and 59.6 parts of deodorized kerosene. Then, after filling the aerosol container and attaching the valve portion, 30 parts of a propellant (liquefied petroleum gas) is pressurized and filled through the valve portion to obtain an oil-based aerosol.

Formulation Example 10 Aqueous aerosol 0.2 parts of each of the compounds (1) to (10) of the present invention, 0.2 part of d-allethrin, 0.2 part of d-phenothrin, 5 parts of xylene,
Aerosol container was filled with a mixture of 3.4 parts of deodorized kerosene and 1 part of emulsifier {Atmos 300 (registered trade name of Atlas Chemical Co.)} and pure 50 parts, and a valve part was attached and sprayed through the valve part. 40 parts of the agent (liquefied petroleum gas) is charged under pressure to obtain an aqueous aerosol.

Formulation Example 11 Heating and smoking agent 100 mg of each of the compounds (1) to (10) of the present invention is dissolved in an appropriate amount of acetone and impregnated into a porous ceramic plate of 4.0 cm × 4.0 cm and 1.2 cm in thickness. Obtain a heated smoker.

Next, Test Examples will show that the compound of the present invention is useful as an active ingredient of a pest controlling agent. The compounds of the present invention are shown by the compound numbers shown in Tables 24 and 25, and the compounds used for comparison and control are shown by the compound symbols shown in Table 27.

[0130]

[Table 27]

Test Example 1 Metamorphosis Inhibitory Action on Larvae of Brown Planthopper The emulsion of the test compound obtained according to Formulation Example 1 was diluted with water to a predetermined concentration and applied to rice seedlings planted with polyethylene cups in 20 ml / 2 pots. Sprayed in proportion. After air-drying, 10 3rd instar larvae of brown planthopper were released per pot.
After a day, the rate of inhibition of emergence was calculated. The results are shown in Table 28.

[0132]

[Table 28]

The compounds (1), (2), and
(4), (5), (6), (7), (8) and (12) inhibited 100% emergence at a test concentration of 0.5 ppm. Further, the compounds (1) and (2) of the present invention showed 100% inhibition of emergence even at the test concentration of 50 ppb.

Test Example 2 Growth Inhibitory Action Against Green Leafhopper The emulsion of the test compound obtained according to Formulation Example 1 is diluted with water to a predetermined concentration, and rice seedlings (length: about 20 cm) planted in pots (1 / 5000a) are diluted. ) Was sprayed at a rate of 40 ml / 2 pots. After air drying, the pot was covered with a wire netting cage, and 10 male and 10 female adult green leafhoppers were released per pot and left in the greenhouse. After about 3 weeks, the number of surviving nymphs of the next generation was investigated to determine the growth inhibition rate. The results are shown in Table 29.

[0135]

[Table 29]

Test Example 3 Proliferation Inhibitory Action against Brown Planthopper The emulsion of the test compound obtained according to Formulation Example 1 was diluted with water to a predetermined concentration, and the rice seedlings (length: about 20 cm) were planted in a pot (1 / 5000a). ) Was sprayed at a rate of 40 ml / 2 pots. After air drying, the pot was covered with a wire netting cage, and 5 male and 5 female adult brown planthoppers were released per pot and left in the greenhouse. After about 3 weeks, the number of surviving nymphs of the next generation was investigated to determine the growth inhibition rate. The results are shown in Table 30.

[0137]

[Table 30]

Test Example 4 Test against Cotton Aphid Emulsion of the test compound obtained according to Formulation Example 1 was diluted with water to a predetermined concentration, and 8-9 days after sowing that cotton aphid first-instar larvae were infested. 3 for potted cotton (primary leaf stage)
Sprayed at a rate of 0 ml / 2 pots. Before and 7
After a day, the total number of cotton aphids on the plants was investigated. The control effect index was calculated by the following formula as a measure of the control effect. The criteria for effect evaluation are as follows: A: Control effect index is 1 or less, and a sufficient growth inhibitory effect is recognized. B: When the control effect index is larger than 1 and 3 or less, the growth suppressing effect is recognized. C: Control effect index is larger than 3, and a slight growth inhibitory effect is recognized. D: The control effect index is the same as that of the untreated group, and no growth inhibitory effect is observed. And The results are shown in Table 31.

[0139]

[Table 31]

[0140]

INDUSTRIAL APPLICABILITY The compound of the present invention comprises a hemiptera pest, a lepidopteran pest, a dipteran pest, a coleopteran pest, a reticulate pest, a total pest, an orthoptera, a hymenoptera, and a hidden pest. It has an excellent control effect against eye pests, lice pests, and other pests such as Lepidoptera, and can be used for various purposes as a pest control agent.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁵ Identification code Internal reference number FI Technical display location C07C 201/12 205/20 6917-4H 253/30 255/54 6917-4H 323/19 7419-4H (72) Inventor Hiroaki Fujimoto 4-2-1 Takashi, Takarazuka-shi, Hyogo Sumitomo Chemical Co., Ltd. (72) Inventor Kenzo Matsuo 4-2-1 Takashi, Takarazuka-shi, Hyogo Sumitomo Chemical Co., Ltd. (72) Inventor Koume Umeda 4-2-1 Takashi, Takarazuka City, Hyogo Prefecture Sumitomo Kagaku Kogyo Co., Ltd.

Claims (4)

[Claims] 1. A general formula: ## STR1 ## [In the formula, R ¹ is an alkyl group having 3 to 8 carbon atoms, an alkoxy group having 3 to 8 carbon atoms, an alkoxyalkyl group having 3 to 8 carbon atoms, an alkenyl group having 3 to 8 carbon atoms,
Alkenyloxy groups having 3 to 8 carbon atoms, all carbon atoms 3
~ 8 alkenyloxyalkyl groups, 3-8 carbon atoms
Haloalkyl groups, haloalkoxy groups having 3 to 8 carbon atoms, haloalkoxyalkyl groups having 3 to 8 carbon atoms, haloalkenyl groups having 3 to 8 carbon atoms, and 3 carbon atoms
~ 8 haloalkenyloxy groups, 3-8 carbon atoms haloalkenyloxyalkyl groups, 3-8 carbon atoms alkynyloxy groups, R ² represents a halogen atom, R ³ independently. R ⁴ represents a hydrogen atom, a halogen atom or a methyl group, R ⁴ represents a hydrogen atom or a methyl group, R ^4
5 independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, and 1 to 1 carbon atoms.
4 alkoxy groups, 1 to 4 carbon atom haloalkoxy groups, 1 to 4 carbon atom alkylthio groups, 1 carbon atom
~ Represents four haloalkylthio groups, 3,4-methylenedioxy group, methoxymethyl group, cyano group, nitro group,
m represents an integer of 1 to 3, and n represents an integer of 1 to 5. ]
An aromatic compound represented by. 2. A general formula: ## STR2 ## [In the formula, R ¹ is an alkyl group having 3 to 8 carbon atoms, an alkoxy group having 3 to 8 carbon atoms, an alkoxyalkyl group having 3 to 8 carbon atoms, an alkenyl group having 3 to 8 carbon atoms,
Alkenyloxy groups having 3 to 8 carbon atoms, all carbon atoms 3
~ 8 alkenyloxyalkyl groups, 3-8 carbon atoms
Haloalkyl groups, haloalkoxy groups having 3 to 8 carbon atoms, haloalkoxyalkyl groups having 3 to 8 carbon atoms, haloalkenyl groups having 3 to 8 carbon atoms, and 3 carbon atoms
~ 8 haloalkenyloxy groups, 3-8 carbon atoms haloalkenyloxyalkyl groups, 3-8 carbon atoms alkynyloxy groups, R ² represents a halogen atom, R ³ independently. It represents a hydrogen atom, a halogen atom or a methyl group, m represents an integer of 1 to 3, and M represents an alkali metal atom or a hydrogen atom. ] And a phenolic compound represented by the general formula: [In the formula, R ⁴ represents a hydrogen atom or a methyl group, R ⁵ independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, and 1 to 4 carbon atoms. An alkoxy group, a haloalkoxy group having 1 to 4 carbon atoms,
An alkylthio group having 1 to 4 carbon atoms, a haloalkylthio group having 1 to 4 carbon atoms, a 3,4-methylenedioxy group,
Represents a methoxymethyl group, a cyano group, or a nitro group, and n is 1
Represents an integer of 5 and A represents a halogen atom. ] The compound shown by these is made to react, The manufacturing method of the aromatic type compound of Claim 1 characterized by the above-mentioned. 3. A general formula: ## STR4 ## [In the formula, R ¹ is an alkyl group having 3 to 8 carbon atoms, an alkoxy group having 3 to 8 carbon atoms, an alkoxyalkyl group having 3 to 8 carbon atoms, an alkenyl group having 3 to 8 carbon atoms,
Alkenyloxy groups having 3 to 8 carbon atoms, all carbon atoms 3
~ 8 alkenyloxyalkyl groups, 3-8 carbon atoms
Haloalkyl groups, haloalkoxy groups having 3 to 8 carbon atoms, haloalkoxyalkyl groups having 3 to 8 carbon atoms, haloalkenyl groups having 3 to 8 carbon atoms, and 3 carbon atoms
~ 8 haloalkenyloxy groups, 3-8 carbon atoms haloalkenyloxyalkyl groups, 3-8 carbon atoms alkynyloxy groups, R ² represents a halogen atom, R ³ independently. It represents a hydrogen atom, a halogen atom or a methyl group, and m represents an integer of 1 to 3. ] And a phenolic compound represented by the general formula: [In the formula, R ⁴ represents a hydrogen atom or a methyl group, R ⁵ independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, and 1 to 4 carbon atoms. An alkoxy group, a haloalkoxy group having 1 to 4 carbon atoms,
An alkylthio group having 1 to 4 carbon atoms, a haloalkylthio group having 1 to 4 carbon atoms, a 3,4-methylenedioxy group,
Represents a methoxymethyl group, a cyano group, or a nitro group, and n is 1
Represents an integer of 5; ] The alcoholic compound shown by these is made to react, The manufacturing method of the aromatic type compound of Claim 1 characterized by the above-mentioned. 4. A pest control agent comprising the aromatic compound according to claim 1 as an active ingredient.