JPH04342568A - Pyridine-based compound, its production and noxious organism controlling agent containing the same as active ingredient - Google Patents

Abstract

PURPOSE:To obtain a new compound, capable exhibiting juvenile hormonal activity as a noxious organism controlling agent and having inhibitory action, etc., on metamorphosis into imagoes. CONSTITUTION:A compound, e.g. 2-chloro-5-{[2-chloro-4-(2-ethylbutyl) phenoxy]methyl}pyridine expressed by formula I [R<1> is 3-8C alkyl, 3-8C alkoxy, etc.; R<2> is halogen or 1-3C alkyl; R<3> is H, halogen or methyl; R<4> is H or methyl; R<5> is H, halogen, 1-3C alkyl or 1-2C haloalkyl; (m) is 1-3]. The aforementioned compound is obtained by reacting a compound expressed by formula II (M is alkali metal or H) with a compound expressed by formula III (A is halogen).

Description

[Detailed description of the invention]

0001

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel pyridine compound, a method for producing the same, and a pest control agent containing the same as an active ingredient.

0002

BACKGROUND OF THE INVENTION The fact that certain pyridine compounds have pest control effects has been described, for example, in West German Published Patent Application No. 2,516,331.

0003

[Problems to be Solved by the Invention] However, these compounds cannot always be said to be sufficient as effective ingredients for pest control agents.

0004

[Means for Solving the Problems] In view of the above-mentioned circumstances, the present inventors have conducted intensive studies to find a compound having a better pest control effect, and have developed the following general formula.
The present invention was completed based on the discovery that the pyridine compound represented by chemical formula 6 has extremely high juvenile hormone-like activity. That is, the present invention provides general formula 6

000
5]

[C6]

[In the formula, R1 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 total carbon atoms, or an alkenyl group having 3 to 8 carbon atoms. , an alkenyloxy group having 3 to 8 carbon atoms, an alkenyloxyalkyl group having 3 to 8 total carbon atoms,
Haloalkyl group having 3 to 8 carbon atoms, haloalkoxy group having 3 to 8 carbon atoms, haloalkoxyalkyl group having 3 to 8 total carbon atoms, haloalkenyl group having 3 to 8 carbon atoms, 3 to 8 carbon atoms haloalkenyloxy group, haloalkenyloxyalkyl group having 3 to 8 carbon atoms in total, or alkynyloxy group having 3 to 8 carbon atoms, R2 is a hydrogen atom, a halogen atom, or an alkyl group having 1 to 3 carbon atoms. R3 independently represents a hydrogen atom, a halogen atom, or a methyl group, R4 represents a hydrogen atom or a methyl group, and R5 represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 3 carbon atoms, or a carbon atom. It represents 1 to 2 haloalkyl groups, and m represents an integer of 1 to 3. ] Pyridine compounds (hereinafter referred to as compounds of the present invention),
The present invention provides a method for producing the same and a pest control agent containing the same as an active ingredient.

The compounds of the present invention differ significantly from most conventional insecticides in that they have excellent juvenile hormone-like activity against insects. That is, it exhibits effects such as inhibiting metamorphosis into adult worms, inhibiting egg hatching, and sterilizing adult worms. As a result, the compounds of the present invention can be used against various pests, including pests that have developed resistance to existing insecticides, such as agricultural, forestry, and horticultural pests.
It mainly acts as a growth regulator, sterilizing agent, ovicidal agent, or growth inhibitor against grain storage pests, satellite pests, etc., 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 R1 is, for example, n-propyl group, isopropyl group,
n-butyl group, sec-butyl group, isobutyl group, t
ert-butyl group, n-pentyl group, neo-pentyl group, 2-methylbutyl group, 2-pentyl group, 3-pentyl group, 2-methyl-2-butyl group, n-hexyl group, 2
-hexyl group, 2-methylpentyl group, 3-methylpentyl group, 4-methylpentyl group, 3,3-dimethylbutyl group, 2,2-dimethylbutyl group, 2-methyl-2-pentyl group, 2-ethylbutyl group group, 3-hexyl group, 4-
Methyl-2-pentyl group, n-heptyl group, 5-methylhexyl group, 4-methylhexyl group, 3-methylhexyl group, 2-methylhexyl group, 2-heptyl group, 3-ethylpentyl group, 2-ethyl group Pentyl group, 3-heptyl group, 4,4-dimethylpentyl group, 3,3-dimethylpentyl group, 2,2-dimethylpentyl group, 2-methyl-
2-hexyl group, n-octyl group, 6-methylheptyl group, 5-methylheptyl group, 4-methylheptyl group, 3
-Methylheptyl group, 2-methylheptyl group, 2-octyl group, 3-octyl group, 4-octyl group, 3-ethylhexyl group, 5,5-dimethylhexyl group, 4,4-dimethylhexyl group, 2,2 -diethylbutyl group, 3,3
-diethylbutyl group, 4-methyl-4-heptyl group, etc.

The alkoxy group having 3 to 8 carbon atoms represented by R1 is, for example, n-propoxy group, isopropoxy group, n-butoxy group, sec-butoxy group, isobutoxy group, tert-butoxy group, n-propoxy group, -pentyloxy group, neo-pentyloxy group, 2-methylbutoxy group, 2-pentyloxy group, 3-pentyloxy group, 2-methyl-2-butoxy group, n-hexyloxy group, 2-hexyloxy group, 2-methylpentyloxy group, 3-methylpentyloxy group, 4-methylpentyloxy group, 3,3-dimethylbutoxy group, 2,2-dimethylbutoxy group, 2-methyl-2-pentyloxy group, 2-ethyl Butoxy group, 3-hexyloxy group, 4-
Methyl-2-pentyloxy group, n-pentyloxy group, 5-methylhexyloxy group, 4-methylhexyloxy group, 3-methylhexyloxy group, 2-methylhexyloxy group, 2-heptyloxy group, 3- Ethylpentyloxy group, 2-ethylpentyloxy group, 3-heptyloxy group, 4,4-dimethylpentyloxy group, 3
, 3-dimethylpentyloxy group, 2,2-dimethylpentyloxy group, 2-methyl-2-hexyloxy group,
n-octyloxy group, 6-methylheptyloxy group,
5-methylheptyloxy group, 4-metalheptyloxy group, 3-methylheptyloxy group, 2-methylheptyloxy group, 2-octyloxy group, 3-octyloxy group, 4-octyloxy group, 3-ethylhexyloxy group group, 5,5-dimethylhexyloxy group, 4,4-dimethylhexyloxy group, 2,2-diethylbutoxy group, 3,3-diethylbutoxy group, 4-methyl-4-heptyloxy group, etc.

The alkoxyalkyl group having 3 to 8 carbon atoms in total represented by R1 includes, for example, ethoxymethyl group, n-propoxymethyl group, isopropoxymethyl group,
sec -butoxymethyl group, isobutoxymethyl group,
(3-pentyloxy)methyl group, (2-ethylbutoxy)methyl group, (3-hexyloxy)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, 2-ethoxybutyl group, 5-ethoxypentyl group, 6-ethoxyhexyl group, etc.

The alkenyl group having 3 to 8 carbon atoms represented by R1 includes, 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-heptenyl group, 7-octenyl group base etc.,

0012
The alkenyloxy group having 3 to 8 carbon atoms represented by R1 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 group, 7-octenyloxy group, etc.

The alkenyloxyalkyl group having 3 to 8 carbon atoms in total represented by R1 includes, for example, allyloxymethyl group, (2-methylallyloxy)methyl group, (
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-hexenyl Oxy)
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, etc.

The haloalkyl group having 3 to 8 carbon atoms represented by R1 is, for example, a 3-fluoropropyl group,
2,2,3,3,3-pentafluoropropyl group, 3-
Chloro-2-butyl 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-bromooctyl group, etc.

The haloalkoxy group having 3 to 8 carbon atoms represented by R1 is, for example, 3-fluoropropoxy group, 2,2,3,3,3-pentafluoropropoxy group, 3-chloro-2- Butoxy 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, 5-chloropentyloxy group, 5-bromopentyloxy group, 6-fluorohexyloxy group, 6-chlorohexyloxy group, 6-bromohexyloxy group, 7-fluoroheptyloxy group, 7 -Bromoheptyloxy group, 8-fluorooctyloxy group, 8-bromooctyloxy group, 2-chloro-
2-methylpropoxy group, 2,3-dichloro-2-methylpropoxy group, 2-chloro-2-methylbutoxy group,
2-chloro-2-methylpentyloxy group, etc.

The haloalkoxyalkyl group having 3 to 8 carbon atoms in total represented by R1 is, for example, (3-fluoropropoxy)methyl group, (2,2,3,3,3-pentafluoropropoxy)methyl group, (3-chloro-2-
butoxy)methyl group, (3-chloropropoxy)methyl group, (2-chloropropoxy)methyl group, (2,3-dichloropropoxy)methyl group, (3-bromopropoxy)methyl group, (2-bromopropoxy)methyl group Base, (3
-iodopropoxy)methyl group, (4-fluorobutoxy)methyl group, (3,3,4,4,4-pentafluoro-2-butoxy)methyl group, (4-chlorobutoxy)methyl group, (3-chloro butoxy)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-(3
-Chloro-2-butoxyethyl group, 1-(3-chloropropoxy)ethyl group, 1-(2-chloropropoxy)ethyl group, 1-(2,3-dichloropropoxy)ethyl group, 1-(3-bromo propoxy)ethyl group, 1-(2-
Bromopropoxy)ethyl group, 1-(3-iodopropoxy)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-chlorobutoxy)ethyl group,
,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-bromo hexyloxy)ethyl group, 2-(3-fluoropropoxy)ethyl group, 2-(
2,2,3,3,3-pentafluoropropoxy)ethyl group, 2-(3-chloro-2-butoxy)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-chlorobutoxy)ethyl group,
-bromobroxy)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, etc.

The haloalkenyl group having 3 to 8 carbon atoms represented by R1 is, for example, 2,3-dichloroallyl group, 2,3-dibromoallyl group, 2-chloro-2-propenyl group, 3-chloro -2-propenyl group, 2-bromo-2-propenyl group, 2-chloromethyl-2-propenyl group, 2-chloro-3-butenyl group, 3-chloro-2-
butenyl group, 4-chloro-2-butenyl group, 4-bromo-2-butenyl group, 7-chloro-7-octenyl group, etc.

The haloalkenyloxy group having 3 to 8 carbon atoms represented by R1 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-2-butenyloxy group, 4-chloro-2-butenyloxy group, 4-bromo-2-butenyloxy group, 7-chloro-7-octenyloxy group, etc.

The haloalkenyloxyalkyl group having 3 to 8 carbon atoms in total represented by R1 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, etc.

The alkynyloxy group having 3 to 8 carbon atoms represented by R1 includes, for example, 2-propynyloxy group, 1-methyl-2-propynyloxy group, 1-ethyl-2-propynyloxy group, 1-ethyl-2-propynyloxy group, -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-
Ethyl-4-methyl-2-pentynyloxy group, 2-hexynyloxy group, 3-hexynyloxy group, 2-heptynyloxy group, 2-octynyloxy group, 7-octynyloxy group, etc.

The alkyl group having 1 to 3 carbon atoms represented by R2 is a methyl group, ethyl group, n-propyl group or isopropyl group,

The alkyl group having 1 to 3 carbon atoms represented by R5 is, for example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, etc.

The haloalkyl group having 1 to 2 carbon atoms represented by R5 is, for example, a trifluoromethyl group, a difluoromethyl group, a 2,2,2-trifluoroethyl group, and the like.

Among the compounds of the present invention represented by the general formula 6, preferred are pyridine compounds in which R2 represents a chlorine atom. As a more preferable compound, R1 is substituted at the 4-position, R2 is a chlorine atom,
(R3) The substitution position of m can be the 5th position, R3 can be a hydrogen atom or a chlorine atom, and m can be 1. In a more preferable compound, R1 is substituted at the 4-position, R2 is substituted at the 4-position,
is a chlorine atom, R3 is a hydrogen atom, R4 is a hydrogen atom, R
5 is a chlorine atom.

The compound of the present invention represented by the general formula 6 can be produced, for example, by the following method. (Production method A) General formula Chemical formula 7

[0026]

[C7]

[In the formula, M represents an alkali metal atom or a hydrogen atom, and R1, R2, R3 and m have the same meanings as above. ] and the general formula 8

[0028]

[Chemical formula 8]

[In the formula, A represents a halogen atom, and R4
and R5 have the same meanings as above. ] It can be produced by reacting with the compound shown below.

Examples of the base used include caustic alkalis such as caustic potash and caustic soda, alkali carbonates such as potassium carbonate and sodium carbonate, alkali metals such as metallic sodium, alkali metal hydrides such as sodium hydride, or sodium methoxide, Examples include organic bases such as sodium ethoxide, triethylamine, and pyridine. In addition, if necessary, ammonium salt (
For example, a catalyst such as triethylbenzylammonium chloride, etc.) may be added.

The reaction temperature can range from -20°C to the boiling point of the solvent used in the reaction, but -5°C
More preferably, the range is from 1 to the boiling point of the solvent used in the reaction.

Although the molar ratio of the raw materials and base to be subjected to the reaction can be set arbitrarily, it is advantageous to carry out the reaction at an equimolar ratio or a ratio close to it.

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

Examples of the solvent used include methanol, ethanol, propanol, isopropanol,
Lower alcohols such as tertiary butyl alcohol, ketones such as acetone and methyl ethyl ketone, hydrocarbons such as benzene and toluene, ethers such as diethyl ether, isopropyl ether, tetrahydrofuran, and dioxane, N,N-dimethylformamide, hexamethyl Examples include amides such as phosphoric triamide, halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, and chlorobenzene, acetonitrile, nitromethane, dimethyl sulfoxide, sulfolane, and water. A mixed solvent of these solvents can also be used if necessary.

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

(Production method B) General formula: Chemical formula 9

[0037]

[Chemical formula 9]

[In the formula, R1, R2, R3 and m
has the same meaning as above. ] and the general formula 10

[0039]

[Chemical formula 10]

[In the formula, R4 and R5 have the same meanings as above. ] It can be produced by reacting with an alcoholic compound shown in the following.

The above reaction is particularly advantageous when R3 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 dehydration catalysts used include inorganic acids such as hydrochloric acid and sulfuric acid, aromatic sulfonic acids or sulfonic acid chlorides, and examples of dehydration agents include dichlorohexylcarbodiimide and diethyl azodicarboxylate. Alternatively, diisopropyl azodicarboxylate and the like can be mentioned.

Examples of the solvent used include hydrocarbons such as benzene and toluene, and halogenated hydrocarbons such as carbon tetrachloride, chloroform and dichloromethane.

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

Although the molar ratio of the raw materials and dehydrating agent to be subjected to the reaction can be set arbitrarily, it is advantageous to carry out the reaction at an equimolar ratio or a ratio close to it.

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

In addition, among the compounds of the present invention, in the case of compounds having an asymmetric carbon atom, the compounds of the present invention are present in the respective optically active isomers ((+)-isomer, (-
)-body) and mixtures thereof in all proportions.

General formula (7) as a raw material for the compound of the present invention
Among the phenolic compounds represented by the above, the phenolic compound in which M represents an alkali metal atom can be derived and synthesized from the phenolic compound represented by the general formula (9). Further, the phenolic compound represented by the general formula 9 can be easily synthesized by using a commercially available compound or by a conventional method from a commercially available compound. Furthermore, among the phenolic compounds represented by the general formula 7 or the general formula 9, those in which R2 represents a chlorine atom are described, for example, in J. Amer. Chem. Soc.
, 73, 2723 (1951), J. Org. Ch
em. , 39, 1160 (1974) and the like. In addition, the general formula
Among the phenolic compounds represented by, those in which R2 represents a chlorine atom are, for example, those represented by the general formula

[0049]

[Chemical formula 11]

[In the formula, R1, R3 and m have the same meanings as above. ] By reacting the phenolic compound shown with a chlorinating agent in the presence of a solvent, R2
It can also be obtained according to a conventional method for synthesizing a phenolic compound represented by the general formula (9) in which is a chlorine atom.

In the above reaction formula, chlorine, t-butyl hypochlorite, sulfuryl chloride, etc. can be used as the chlorinating agent. Further, a solvent can be used if necessary, 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 selected depending on the type of chlorinating agent. The reaction temperature is
The range can be from -78°C to the boiling point of the solvent or chlorinating agent (sulfuryl chloride, etc.) used in the reaction, but -
The range is preferably from 20°C to the boiling point of the solvent or chlorinating agent (such as sulfuryl chloride) used in the reaction. Although the molar ratio of the raw materials and chlorinating agent to be subjected to the reaction can be set arbitrarily, it is advantageous to carry out the reaction at an equimolar ratio or a ratio close to it. After the reaction is completed, the reaction solution can be subjected to conventional post-treatments such as organic solvent extraction and concentration to obtain the target compound. If necessary, chromatography, distillation,
It can also be purified by conventional operations such as recrystallization.

General formula (8) as a raw material for the compound of the present invention
Alternatively, the compound represented by the general formula 10 can be used as a commercially available compound, or can be easily synthesized from a commercially available compound by a conventional method.

Next, the compounds of the present invention that can be produced according to these production methods are shown in Tables 1 to 27. However, these compounds are for illustrative purposes only, and the present invention is not limited thereto.

[0054]

[Table 1]

[0055]

[Table 2]

[0056]

[Table 3]

[0057]

[Table 4]

[0058]

[Table 5]

[0059]

[Table 6]

[0060]

[Table 7]

[0061]

[Table 8]

[0062]

[Table 9]

[0063]

[Table 10]

[0064]

[Table 11]

[0065]

[Table 12]

[0066]

[Table 13]

[0067]

[Table 14]

[0068]

[Table 15]

[0069]

[Table 16]

[0070]

[Table 17]

[0071]

[Table 18]

[0072]

[Table 19]

[0073]

[Table 20]

[0074]

[Table 21]

[0075]

[Table 22]

[0076]

[Table 23]

[0077]

[Table 24]

[0078]

[Table 25]

[0079]

[Table 26]

[0080]

[Table 27]

[0081] Examples of pests against which the compounds of the present invention are effective include the following.

Hemiptera pests: planthoppers such as the brown planthopper, white-backed planthopper, and brown planthopper, leafhoppers such as the black-spotted leafhopper, black-spotted leafhopper, black-spotted leafhopper, brown leafhopper, brown leafhopper, black-and-white leafhopper, cotton aphid, green peach aphid, etc. Aphids, stink bugs, whiteflies such as tobacco whitefly, and whitefly, scale insects, ground beetles, psyllids, etc.

[0083] Lepidopteran insect pests, such as the Japanese armyworm moth (Nikamei moth), the brown borer moth, and the Japanese armyworm moth, the armyworms such as the armyworm, the fall armyworm, and the armyworm moth, the white butterflies such as the white cabbage butterfly, the yellow leaf moths such as the white leaf moth, the silver leaf moth, the leafminer moth, and the Japanese leafminer moth. , Pests of the genus Agrotis (A
grothis spp. ), Heliotis pests (H
eliothis spp. ), diamondback moth, burr moth, carp moth, etc.

[0084] Diptera pests Culex mosquitoes such as Culex mosquitoes and Culex pipiens; Aedes mosquitoes such as Aedes aegypti and Aedes albopictus; Anopheles mosquitoes such as Anopheles albopictus; Chironomid mosquitoes; house flies such as house flies and giant house flies; Hana flies such as onion flies, fruit flies, fruit flies, fruit flies, fruit flies,
Butterflies, horseflies, blackflies, stable flies, etc.

008
5] Coleoptera Pests Corn rootworms such as Western corn rootworm and Southern corn rootworm, scarab beetles such as the Japanese corn rootworm and Japanese corn rootworm, weevils such as the brown weevil, rice water weevil, and bean weevil, and mealworms such as the brown rice beetle and the brown corn rootworm spp., potato beetles such as the yellow flea beetle and cucurbit beetles, leaf beetles, Epilachna spp.

[0086] Pests of the order Ophthalmoptera: German cockroach, black cockroach, American cockroach, brown cockroach, small cockroach, etc.

[0087] Grossopteran pests such as southern yellow thrips, brown brown thrips, and red thrips, etc.

Hymenoptera pests Ants, sawflies such as sawflies, etc.

Orthoptera pests Mole crickets, grasshoppers, etc.

0090 Cryptopteran pests Human flea etc.

0091 Pests of the order Liceformes Human lice, pubic lice, etc.

[0092] It is effective against isopteran pests such as the Japanese termite and the domestic termite. Furthermore, among these, it is more suitable for controlling Hemiptera pests, and is particularly effective against planthoppers and leafhoppers that damage rice crops, and exhibits an excellent control effect.

[0093] By adding other insecticides and/or acaricides, the compound of the present invention can be practically applied for controlling pests to a wider variety of pests and to a more diverse range of use situations. Suitable additives include, for example, BPMC (2
-sec -butylphenylmethylcarbamate], benfuracarb[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], methomyl [S-methyl-N-[(methylcarbamoyl)oxy]thioacetimidate],
Ethiophenecarb [2-(ethylthiomethyl)phenylmethylcarbamate], aldicarb [2-methyl-
Carbamate compounds such as 2-(methylthio)propionaldehyde O-methylcarbamoyloxy], oxamyl [N,N-dimethyl-2-methylcarbamoyloxyimino-2-(methylthio)acetamide],

Ethofenprox [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], fenpropathrin [( 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,3RS)-
3-(2,2-dichlorovinyl)-2,2-methylcyclopropanecarboxylate], cyhalothrin [(RS
)-α-cyano-3-phenoxybenzyl (Z)-(1
RS,3RS)-3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarboxylate], deltamethrin [(S)-α-
Cyano-m-phenoxybenzyl (1R,3R)-3(
2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylate], cycloprothrin [(RS
)-α-cyano-3-phenoxybenzyl (RS)-2
, 2-dichloro-1-(4-ethoxyphenyl)cyclopropanecarboxylate] and other pyrethroid compounds;

Buprofezin [2-tert-butylimino-3-isopropyl-5-phenyl-1,3,5-
thiadiazine derivatives such as triadiazinan-4-one], nitroimidazolidine derivatives such as imidacloprid [1-(6-chloro-3-pyridylmethyl)-N-nitroimidazolidin-2-ylideneamine], cartap [
S,S'-(2-dimethylaminotrimethylene)bis(
thiocarbamate)], thiocyclam [N,N-dimethyl-1,2,3-trithian-5-ylamine], bensultap [S,S'-2-dimethylaminotrimethylene di(benzenethiosulfonate)], etc. Nelystoxin derivative, 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 [1,
Chlorinated hydrocarbon compounds such as 2,3,4,5,6-hexachlorocyclohexane], chlorfluavron [1-(
3,5-dichloro-4-(3-chloro-5-trifluoromethylpyridin-2-yloxy)phenyl]-3-
(2,6-difluorobenzoyl)urea], teflubenzuron [1-(3,5-dichloro-2,4-difluorophenyl)-3-(2,6-difluorobenzoyl)
urea], flufenoxuron [1-[4-(2-chloro-4-trifluoromethylphenoxy)-2-fluorophenyl]-3-(2,6-difluorobenzoyl)
benzoylphenylurea-based compounds such as urea], amitraz [[N,N'[(methylimino)dimethylidine]
di-2,4-xylidine], chlordimeform [N'-
(4-chloro-2-methylphenyl)-N,N-dimethylmetanimidamide] and other formamidine derivatives.

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 of the ingredients described above, but it is usually used in the presence of a solid carrier, liquid carrier, gaseous carrier, or bait. If necessary, surfactants and other formulation auxiliaries are added to produce flowable agents such as oils, emulsions, wettable powders, suspensions and emulsions in water, granules, powders, etc.
It is used in formulations such as aerosols, heating smokers such as self-combustion type smokers, chemical reaction type smokers, and porous ceramic plate smokers, ULV agents, and poison baits.

These preparations usually contain the compound of the present invention as an active ingredient in an amount of 0.001% to 95% by weight. Solid carriers used in formulation include, for example, clays (kaolin clay, diatomaceous earth, synthetic hydrated silicon oxide, bentonite, fubasami clay, acid clay, etc.), talcs, ceramics, and other inorganic minerals (sericite, quartz,
Sulfur, activated carbon, calcium carbonate, hydrated silica, etc.), chemical fertilizers (ammonium sulfate, ammonium phosphorus, ammonium nitrate, urea, ammonium chloride, etc.), and other fine powders or granules.As liquid carriers, for example, water, alcohol, etc. (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, carbon tetrachloride, etc.), dimethyl sulfoxide, vegetable oils such as soybean oil, cottonseed oil, etc.; Examples of the agent include chlorofluorocarbon gas, butane gas, LPG (liquefied petroleum gas), dimethyl ether,
Examples include carbon dioxide gas.

Examples of surfactants include alkyl sulfate esters, alkyl sulfonates, alkylaryl sulfonates, alkylaryl ethers and polyoxyethylenic products thereof, polyethylene glycol ethers, polyhydric alcohol esters, and sugar alcohols. Examples include derivatives.

Examples of formulation auxiliaries such as fixing agents and dispersants include casein, gelatin, polysaccharides (starch powder,
Gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, sugars, synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.), etc. Stabilizers include PAP (acidic phosphoric acid, etc.). isopropyl), BHT (2,
6-di-tert-butyl-4-methylphenol),
Examples include BHT (a mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol), vegetable oil, mineral oil, surfactant, fatty acid or its ester, and the like.

[0100] Examples of base materials for self-combusting smoke agents include nitrates, nitrites, guanidine salts, potassium chlorate,
Combustion exothermic agents such as nitrocellulose, ethyl cellulose, and wood flour; thermal decomposition stimulators such as alkali metal salts, alkaline earth metal salts, dichromates, and chromates; oxygen supply agents such as potassium nitrate; melamine and wheat starch. Examples include combustion supporting agents such as, fillers such as diatomaceous earth, binders such as synthetic glues, etc. Examples of base materials for chemically reactive smoke agents include alkali metal sulfides, polysulfides, hydrosulfides, hydrated salts,
Exothermic agents such as calcium oxide, carbonaceous substances, iron carbide, catalyst agents such as activated clay, organic blowing agents such as azodicarbonamide, benzenesulfonylhydrazine, dinitrosopentamethylenetetramine, polystyrene, polyurethane, natural fiber pieces, synthetic fibers Examples include fillers such as pieces.

Poisonous bait base materials include, for example, grain flour, vegetable essential oils, sugar, bait components such as crystalline cellulose, antioxidants such as dibutylhydroxytoluene and nordihydroguaiaretic acid, preservatives such as dehydroacetic acid, and chili peppers. Examples include agents to prevent accidental ingestion of powder, etc., and attractive flavorings such as cheese flavoring and onion flavoring.

The formulation of flowables (suspensions or emulsions in water) generally contains 1 to 75% of the compound in a proportion of 0.5 to 1
5% dispersant, 0.1-10% suspension aid (e.g.
compounds that impart protective colloids and thixotropic properties),
In water containing 0 to 1.0% of suitable adjuvants (e.g. antifoaming agents, rust inhibitors, stabilizers, spreading agents, penetration aids, antifreeze agents, antibacterial agents, antismoke agents, etc.) It can be obtained by finely dispersing it. It is also possible to use an oil in which the compound hardly dissolves in place of water to form a suspension in oil. As the protective colloid, for example, gelatin, casein, gums, cellulose ether, polyvinyl alcohol, etc. are used. Examples of compounds that impart thixotropy include bentonite, aluminum magnesium silicate, xanthan gum, and polyacrylic acid.

[0103] The preparation thus obtained can be used as it is or diluted with water or the like. Also, other insecticides,
It can also be used simultaneously with or without mixing with nematicides, acaricides, fungicides, herbicides, plant growth regulators, synergists, fertilizers, soil conditioners, animal feed, etc.

When the compound of the present invention is used as an agricultural pest control agent, the application amount is usually 0.001 to 500 g per 10 ares, preferably 0.1 g.
g to 500 g. When using emulsions, wettable powders, flowables, etc. diluted with water, the application concentration is usually 0.
．． 0001ppm to 1000ppm, granules,
Powders and the like should be applied in their original form without any dilution. In addition, when used as pest control agents for epidemic prevention, emulsions, hydrating agents, flowable agents, etc. are usually 0.0001
Apply diluted to ppm ~ 10,000 ppm, oil agent,
Aerosols, smoke agents, ULV agents, poison baits, etc. should be applied as is.

[0105] These application amounts and application concentrations vary depending on the situation such as the type of preparation, application time, application location, application method, type of pest, and degree of damage, and may be increased or increased without regard to the above range. It can be reduced.

[0106]

EXAMPLES The present invention will be explained 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, a production example of the compound of the present invention will be shown.

Production Example 1 Production of 2-chloro-5-{[2-chloro-4-(2-ethylbutyl)phenoxy]methyl}pyridine by (Production Method A) Potassium carbonate 0.27 g, 2-chloro-4 -(2-ethylbutyl)phenol 0.40 g, 2-chloro-5-(
A mixture of 0.30 g of chloromethyl)pyridine and 15 ml of N,N-dimethylformamide was stirred at room temperature overnight. After pouring the reaction solution into ice water, add 100ml of diethyl ether.
Extracted twice with l. The ether layers were combined, washed with water, dried, and concentrated to obtain a crude product. This crude product was subjected to silica gel chromatography to obtain 0.35 g of 2-chloro-5-{[2-chloro-4-(2-ethylbutyl)phenoxy]methyl}pyridine (hereinafter referred to as compound (1)). I got it. Yield: 52% m. p. :52.4℃

Production Example 2 2-chloro-5-{[2-chloro-4-(isobutoxymethyl)
Production method of phenoxy]methyl}pyridine Potassium carbonate 0.35g (2.56mmol), 2-chloro-4-(isobutoxymethyl)phenol 0.50
A mixture of 0.38 g (2.33 mmol) of 2-chloro-5-(chloromethyl)pyridine and 15 ml of N,N-dimethylformamide was stirred at room temperature overnight. After the reaction solution was poured into ice water, it was extracted twice with 100 ml of diethyl ether. Together with the ether layer,
After washing with water and drying, the mixture was concentrated to obtain a crude product. This crude product was subjected to silica gel chromatography, and 2-chloro-5
-[2-chloro-4-(isobutoxymethyl)phenoxy]methyl}pyridine (hereinafter referred to as compound (2))
0.48g was obtained. Yield: 61% m. p. :51.4℃

Production Example 3 Production of 2-chloro-5-{[2-chloro-4-(2-chloro-2-methylpropoxy)phenoxy]methyl}pyridine by (Production Method A) Potassium carbonate 0.28 g ( 2.2 mmol), 2-chloro-4-(2-chloro-2-methylpropoxy)phenol 0.47 g (2.0 mmol), 2-chloro-5-
(chloromethyl)pyridine 0.32g (2.0mmol
) and 15 ml of N,N-dimethylformamide are stirred at room temperature overnight. The reaction solution was poured into ice water and extracted twice with 100 ml of diethyl ether. The ether layers are combined, washed with water, dried, and concentrated to obtain a crude product. This crude product was subjected to silica gel chromatography to obtain 2-chloro-5-{[2-chloro-
4-(2-chloro-2-methylpropoxy)phenoxy]methyl}pyridine (hereinafter referred to as compound (3)) is obtained.

Production Example 4 2-chloro-5-{[2-chloro-4-(sec -butoxy) by (Production method B)
Production method of phenoxy]methyl}pyridine 2-chloro-4-(2-methylpropoxy)phenol 0.74g, p-ethylbenzyl alcohol 0.38g
A mixture of 0.70 g of triphenylphosphine, 0.46 g of diethyl azodicarboxylate 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. After concentrating the filtrate, it was subjected to silica gel chromatography to obtain 2-chloro-5-{[2-chloro-4-
0.26 g of (sec-butoxy)phenoxy]methyl}pyridine (hereinafter referred to as compound (4)) was obtained. Yield: 31% nD 25.0:1.5638

Production Example 5 2-Iodo-5-{[2-chloro-4-(sec -butoxy) by (Production Method B)
Production method of 2-chloro-4-(2-methylpropoxy)phenol 0.40 g (2.02 mmol), 2-iodo-5-(
Hydroxymethyl)pyridine 0.47g (2.02mm
ol), triphenylphosphine 0.53 g (2.02
A solution of 0.41 g (2.02 mmol) of diisopropylazodicarboxylate in 5 ml of tetrahydrofuran is slowly added dropwise at room temperature (approximately 20° C.) under stirring. After completion of the dropwise addition, the mixture was stirred at room temperature for 7 hours, the reaction solution was concentrated, 50 ml of diethyl ether was added, and the precipitate was filtered. After concentrating the filtrate, it was subjected to silica gel chromatography to obtain 2-iodo-5-{[2-chloro-4-(sec
-butoxy)phenoxy]methyl}pyridine (hereinafter referred to as
It is referred to as compound (5). ).

[0112] Next, formulation examples will be shown. In addition, parts represent parts by weight, and the compounds of the present invention are represented by the above compound numbers.

Formulation Example 1 Emulsion 10 parts each of the compounds (1) to (5) of the present invention were dissolved in 35 parts of xylene and 35 parts of dimethylformamide, and 14 parts of polyoxyethylene styryl phenyl ether was dissolved therein.
1 part and 6 parts of calcium dodecylbenzenesulfonate were added and mixed with thorough stirring to obtain each 10% emulsion.

Formulation Example 2 Wettable powder 20 parts each of the compounds (1) to (5) of the present invention were mixed with 4 parts of sodium lauryl sulfate and 2 parts of calcium ligninsulfonate.
1 part, 20 parts of synthetic hydrated silicon oxide fine powder, and 54 parts of diatomaceous earth were added to the mixture, and the mixture was stirred and mixed with a juice mixer to obtain each 20% hydrating powder.

Formulation Example 3 Granules 5 parts of the compound of the present invention (4), 5 parts of sodium dodecylbenzenesulfonate, 30 parts of bentonite and 60 parts of clay
1 part and stir thoroughly to mix. Next, an appropriate amount of water is added to the mixture, which is further stirred, granulated using a granulator, and dried through ventilation to obtain 5% granules.

Formulation Example 4 Granules To 5 parts each of compounds (1) and (2) of the present invention, 5 parts of synthetic hydrous silicon oxide fine powder, 5 parts of sodium dodecylbenzenesulfonate, 30 parts of bentonite and 55 parts of clay were added. Stir thoroughly to mix. Next, an appropriate amount of water is added to these mixtures, which are further stirred, granulated using a granulator, and dried through ventilation to obtain each 5% granule.

Formulation Example 5 Powder 0.3 parts of the compound of the present invention (4), 1 part of synthetic hydrated silicon oxide fine powder, and as a coagulant the trade name: Driles B (manufactured by Sankyo Co., Ltd.)
After thoroughly mixing 1 part of clay and 7.7 parts of clay in a mortar, the mixture is stirred and mixed with a juice mixer. 90 parts of cut clay is added to the resulting mixture and mixed in a bag to obtain a powder.

Formulation Example 6 Powder 0.3 parts each of the compounds (1) and (2) of the present invention and 0.03 part of synthetic hydrous silicon oxide fine powder are thoroughly stirred and mixed with a juice mixer, and then pulverized with a centrifugal pulverizer. . To the obtained pulverized mixture were added 0.97 parts of synthetic hydrous silicon oxide fine powder, 1 part of the trade name Driles B (manufactured by Sankyo Co., Ltd.) as a flocculant, and 7.7 parts of clay, and after mixing well in a mortar, the mixture was mixed in a juice mixer. Stir to mix. 90 parts of cut clay was added to the resulting mixture and mixed in a bag to obtain each powder.

Formulation Example 7 Powder 0.3 parts of the compound of the present invention (4), 2 parts of BPMC (O-sec-butylphenyl N-methyl carbamate) as a carbamate compound, 3 parts of synthetic hydrous silicon oxide fine powder, as a flocculant After thoroughly mixing 1 part of the product name Driles B (manufactured by Sankyo Co., Ltd.) and 3.7 parts of clay in a mortar, the mixture is stirred and mixed with a juice mixer. 90 parts of cut clay was added to the resulting mixture and mixed in a bag to obtain a powder.

Formulation Example 8 Powder 0.3 parts each of compounds (1) and (2) of the present invention and 0.03 part of synthetic hydrated silicon oxide fine powder are thoroughly stirred and mixed with a juice mixer, and then pulverized with a centrifugal pulverizer. . BPMC (O
-sec-butylphenyl N-methylcarbamate) 2 parts, 2.97 parts of synthetic hydrous silicon oxide fine powder, 1 part of the trade name Drileth B (manufactured by Sankyo Co., Ltd.) as a flocculant, and 3.7 parts of clay were added in a mortar. After mixing well, mix using a juice mixer. 90 parts of cut clay was added to the resulting mixture and mixed in a bag to obtain each powder.

Formulation Example 9 Flowable agent Compound of the present invention (
4) Add 10 parts to 40 parts of an aqueous solution containing 6 parts of polyvinyl alcohol, and stir with a mixer to obtain a dispersant. To this, 40 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate are added, and further, 10 parts of propylene glycol are added and mixed with gentle stirring to obtain a 10% emulsion in water.

Formulation Example 10 Flowable Agent 20 parts each of the compounds (1) and (2) of the present invention and 1.5 parts of sorbitan trioleate were mixed with 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol, and the mixture was mixed with a sand grinder. After finely pulverizing (particle size 3μ or less), 40 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate were added, and further 10 parts of propylene glycol were added and mixed by stirring. A 20% suspension in water is obtained.

Formulation Example 11 Oil Agent 0.1 part of each of the compounds (1) to (5) of the present invention was dissolved in 5 parts of xylene and 5 parts of trichloroethane, and this was mixed with 89.9 parts of deodorized kerosene. .1% oil solution is obtained.

Formulation Example 12 Oil aerosol 0.1 part each of the compounds (1) to (5) of the present invention, 0.1 part of tetramethrin.
2 parts, d-phenothrin 0.1 part, trichloroethane 1 part
After mixing and dissolving 59.6 parts of deodorized kerosene and 59.6 parts of deodorized kerosene, filling them into an aerosol container and attaching a valve part, 30 parts of a propellant (liquefied petroleum gas) was pressurized and filled through the valve part to form each oil-based aerosol. get.

Formulation Example 13 Aqueous aerosol: 0.2 parts each of the compounds (1) to (5) of the present invention, 0.2 parts of d-allethrin.
2 parts of d-phenothrin, 0.2 parts of xylene, 3.4 parts of deodorized kerosene, and 1 part of emulsifier {Atmos 300 (registered trademark of Atlas Chemical Co., Ltd.)} were mixed and dissolved;
An aerosol container is filled with 50 parts of pure water, a valve part is attached, and 40 parts of a propellant (liquefied petroleum gas) is pressurized and filled through the valve part to obtain each aqueous aerosol.

Formulation Example 14 Heated smoking agent Compound of the present invention (
100 mg of each of 1) to (5) was dissolved in an appropriate amount of acetone and impregnated into a 4.0 cm x 4.0 cm, 1.2 cm thick porous ceramic plate to obtain each hot smoking agent.

Next, the usefulness of the compound of the present invention as an active ingredient of a pest control agent will be shown by test examples. The compounds of the present invention are indicated by the above-mentioned compound numbers, and the compounds used for comparison are indicated below together with their compound symbols. (A) 3-[(4-phenoxyphenoxy)methyl]pyridine Compound described in West German Published Patent Application No. 2,516,331

Test Example 1 Metamorphosis inhibitory effect on brown planthopper larvae An emulsion of the test compound obtained according to Preparation Example 1 was diluted with water to a predetermined concentration and applied to rice seedlings planted in polyethylene cups in a volume of 20 ml/2 pots. It was distributed in proportion. After air drying, 10 brown planthopper 3rd instar larvae were released per pot.
After several days, the inhibition rate of emergence was determined. As a result, the compound of the present invention (
1), (2) and (4) each at a test concentration of 50 ppm
, 5ppm, and 0.5ppm inhibited 100%. On the other hand, compound (A) had an eclosion inhibition rate of 10% at a test concentration of 50 ppm.

[0129]

[Effects of the Invention] The compounds of the present invention are effective against Hemiptera pests, Lepidoptera pests, Diptera pests, Coleoptera pests, Reciptate pests, Thymoptera pests, Orthoptera pests, Hymenoptera pests, and cryptopteran pests. It has an excellent control effect on insect pests of the Order order, Prunidae order, Isoptera order pests, etc., and can be used for various purposes as a pest control agent.

Claims (4)

[Claims] Claim 1: General formula: Chemical formula 1: [In the formula, R1 is an alkyl group having 3 to 8 carbon atoms, an alkoxy group having 3 to 8 carbon atoms, or an alkoxyalkyl group having 3 to 8 carbon atoms in total. , alkenyl group having 3 to 8 carbon atoms, alkenyloxy group having 3 to 8 carbon atoms, alkenyloxyalkyl group having 3 to 8 total carbon atoms, 3 to 8 carbon atoms
8 haloalkyl groups, haloalkoxy groups with 3 to 8 carbon atoms, haloalkoxyalkyl groups with 3 to 8 total carbon atoms, haloalkenyl groups with 3 to 8 carbon atoms, 3 carbon atoms
~8 haloalkenyloxy groups, haloalkenyloxyalkyl groups with 3 to 8 total carbon atoms, alkynyloxy groups with 3 to 8 carbon atoms, R2 is a halogen atom or an alkyl group with 1 to 3 carbon atoms , R3 independently represents a hydrogen atom, a halogen atom or a methyl group,
R4 represents a hydrogen atom or a methyl group, R5 represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 3 carbon atoms, or a haloalkyl group having 1 to 2 carbon atoms, m is 1
Represents an integer from ~3. ] A pyridine compound represented by [Claim 2] General formula: [Formula 2] [In the formula, R1 is an alkyl group having 3 to 8 carbon atoms, an alkoxy group having 3 to 8 carbon atoms, or an alkoxyalkyl group having 3 to 8 total carbon atoms. , alkenyl group having 3 to 8 carbon atoms, alkenyloxy group having 3 to 8 carbon atoms, alkenyloxyalkyl group having 3 to 8 total carbon atoms, 3 to 8 carbon atoms
8 haloalkyl groups, haloalkoxy groups with 3 to 8 carbon atoms, haloalkoxyalkyl groups with 3 to 8 total carbon atoms, haloalkenyl groups with 3 to 8 carbon atoms, 3 carbon atoms
~8 haloalkenyloxy groups, haloalkenyloxyalkyl groups with 3 to 8 total carbon atoms, alkynyloxy groups with 3 to 8 carbon atoms, R2 is a halogen atom or an alkyl group with 1 to 3 carbon atoms , R3 independently 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. [In the formula, R4 represents a hydrogen atom or a methyl group, and R5
represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 3 carbon atoms, or a haloalkyl group having 1 to 2 carbon atoms, and A represents a halogen atom. 2. The method for producing a pyridine compound according to claim 1, which comprises reacting the pyridine compound with a compound represented by the following. [Claim 3] General formula: [Formula 4] [In the formula, R1 is an alkyl group having 3 to 8 carbon atoms, an alkoxy group having 3 to 8 carbon atoms, or an alkoxyalkyl group having 3 to 8 total carbon atoms. , alkenyl group having 3 to 8 carbon atoms, alkenyloxy group having 3 to 8 carbon atoms, alkenyloxyalkyl group having 3 to 8 total carbon atoms, 3 to 8 carbon atoms
8 haloalkyl groups, haloalkoxy groups with 3 to 8 carbon atoms, haloalkoxyalkyl groups with 3 to 8 total carbon atoms, haloalkenyl groups with 3 to 8 carbon atoms, 3 carbon atoms
~8 haloalkenyloxy groups, haloalkenyloxyalkyl groups with 3 to 8 total carbon atoms, alkynyloxy groups with 3 to 8 carbon atoms, R2 is a halogen atom or an alkyl group with 1 to 3 carbon atoms , R3 independently represents a hydrogen atom, a halogen atom or a methyl group,
m represents an integer of 1 to 3. [In the formula, R4 represents a hydrogen atom or a methyl group, and R5
represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 3 carbon atoms, or a haloalkyl group having 1 to 2 carbon atoms. 2. The method for producing a pyridine compound according to claim 1, which comprises reacting the pyridine compound with an alcohol compound represented by the following. 4. A pest control agent containing the pyridine compound according to claim 1 as an active ingredient.