Ether compounds and their use

Details Ether compounds and their use Ether compounds and their use

1996-12-06

1999-03-16

Dees, Jose G.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548255, 5483561, 548182, 5462684, 546302, 546290, 514345, 514365, 514406, 514422, C07D40112, C07D40312, A01N 4354, A01N 4356

Patent

active

058832629

DESCRIPTION:

BRIEF SUMMARY
This application has been filed under USC 371 as a National stage application of PCT/JP95/00763 filed Apr. 19, 1995.


TECHNICAL FIELD

The present invention relates to ether compounds and their use. More particularly, the present invention relates to ether compounds which have excellent controlling effects against harmful organisms and to harmful-organism controlling agents containing them as active ingredients.


DISCLOSURE OF THE INVENTION

The present inventors have intensively studied to find compounds which have excellent controlling effects against harmful organisms. As a result, they have found that ether compounds of the general formula P-1 as depicted below have excellent controlling effects against harmful organisms, thereby completing the present invention.
Thus the present invention provides ether compounds (hereinafter referred to as the present compound(s)) of the general formula: ##STR4## wherein R.sup.1 is hydrogen or chlorine; R.sup.2 and R.sup.3 are independently hydrogen or methyl; ##STR5## wherein R.sup.4 is hydrogen, chlorine or methyl; and R.sup.5 and R.sup.6 are independently hydrogen or chlorine; ##STR6## wherein R.sup.7 and R.sup.8 are independently hydrogen or fluorine; and X is oxygen or sulfur; and harmful-organism controlling agents containing them as active ingredients.


EMBODIMENTS FOR MAKING THE INVENTION

In the present compounds, it is preferred from the viewpoint of harmful-organism controlling activity that A is a group of the general formula: ##STR7## wherein R.sup.4 is as defined above. Among them, a group wherein R.sup.4 is hydrogen is preferred, and R.sup.1 is preferably hydrogen.
The present compounds can be produced, for example, by the following processes.
(Production process a)
This is a production process in which a phenol derivative of the general formula: ##STR8## wherein R.sup.1 and A are as defined above, with a compound of the general formula: ##STR9## wherein R.sup.2, R.sup.3, B and X are as defined above; and L is halogen (e.g., chlorine, bromine, iodine), mesyloxy or tosyloxy.
(Production process b)
This is a production process in which a compound of the general formula: ##STR10## wherein R.sup.1, R.sup.2, R.sup.3, A and X are as defined above, or an alkali metal salt thereof (e.g., lithium salt, sodium salt, potassium salt), is reacted with a compound of the general formula:
(Production process c)
This is a production process in which a compound of the general formula: ##STR11## wherein R.sup.1, R.sup.2, R.sup.3, A and L are as defined above, is reacted with a compound of the general formula: (e.g., lithium salt, sodium salt, potassium salt).
In the production processes a, b and c, the reaction is preferably effected in the presence of a base without any solvent or in an inert organic solvent (however, when an alkali metal salt of the compound of the general formula P-5 or P-8 is used for the reaction in the production process b and c, there is no need to use a base).
This reaction is usually effected in an inert organic solvent. As the solvent which can be used, there can be mentioned, for example, aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; nitriles such as acetonitrile, propionitrile and isobutyronitrile; ketones such as acetone, methyl isobutyl ketone and methyl ethyl ketone; methanol, ethanol, n-propyl alcohol and the like; ethers such as methoxyethane, tetrahydrofuran and dioxane; polar solvents such as N,N-dimethylformamide, N,N-di-methylacetamide, dimethylsulfoxide, sulforane and hexamethylphosphoric triamide; water; or mixtures thereof. To make more smooth progress in the reaction, phase transfer catalysts may be added, such as benzyltriethylammonium chloride and tetra-n-butylammonium bromide.
As the base which can be used, there can be mentioned, for example, alkali metals such as sodium and potassium; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; alkali metal hydrides such as sodium hydride; metal alkoxides suc

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