JPS58105932A - Diphenyl ether derivative, its preparation and herbicide containing said compound - Google Patents

Abstract

NEW MATERIAL:The diphenyl ether derivative of formulaI(Y1 is halogen or nitro; Y2 is halogen or trifluoromethyl; Z is H, halogen or nitro). EXAMPLE:2'- Nitro-4'- trifluoromethylphenyl-3-( 2,2-dichlorocyclopropyl-methyl )- 4-nitrophenyl ether. USE:Herbicide having high selectivity and extremely low toxicity to man, beast, fish and shellfish. PROCESS:The compound of formulaIis prepared by reacting the phenoxy-phenol derivative of formula II with dichlorocyclopropylmethyl halide of formula III (X is halogen) in the presence of a base such as NaOH, KOH, etc. in an inert organic solvent such as methyl alcohol, etc.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to the general formula (11 (wherein ylFi represents a halogen atom or a nitro group, Y
There are 84 diphenyl ethers represented by (l represents a halogen atom or a trifluoro group, 2 represents a hydrogen droplet and a nitro group across the halogen atom), all of which are new compounds and have excellent herbicidal activity. It is.

The present inventors conducted intensive research to develop a so-called highly selective herbicide f, which is highly safe for crops and has high herbicidal activity against weeds, and as a result, the general formula [! The compound represented by ] shows a high degree of selectivity between crops and weeds, and is also highly selective between humans and livestock.

He discovered a herbicide with excellent characteristics such as extremely low toxicity for seafood, and completed the present invention.

As is clear from the test examples, the compound of the present invention represented by the general formula [1] shows almost no phytotoxicity to cultivated crops, regardless of the treatment method, and is moreover harmful to weeds. It exhibits extremely strong herbicidal activity and has remarkable selective herbicidal activity.

The compounds of the present invention represented by general formula (1) are all new compounds and can be produced by the method shown below.

When manufacturing, first the general formula [setting] (in the formula Yl,
Y, and a phenoxyphenol derivative represented by (wherein X represents a halogen atom) (in which X represents a halogen atom), a compound of the general formula ( The compound represented by 1) can be easily produced.

The reaction is preferably carried out in an inert solvent in the presence of a base as an acid acceptor.

Examples of the acid acceptor used here include inorganic compounds such as sodium hydroxide, potassium hydroxide, sodium bicarbonate, and calcium carbonate, and pyridine.

Examples include organic compounds such as triethylamine.

As a solvent, it depends on the acid acceptor used, but common organic solvents such as methyl alcohol, ethyl alcohol,
Acetone, acetic acid ethyl ester, chloroform, benzene, toluene, dioxane.

Tetrahydro7rane, dimethylformado, dimethyl sulfoxide, etc. can be used.

Also, it can be used by mixing it with water if necessary.

The reaction temperature varies depending on the type of solvent used, but ranges from room temperature to 1
The temperature can be freely selected up to around 30°C. Preferably it is 30 to 80°C.

Next, a manufacturing example will be given and explained.

Manufacturing example.

(Olomethylphenoxy) Phenol L72F was dissolved in acetone 15-. In addition to this, calcium carbonate L5t and l-bromomethyl-2,2-dicyclopropane L
22f was added and reacted with stirring for 5 hours under rapid flow.9 After distilling off the acetone, 20d of water and 20d of acetic acid ethyl ester were added to the residue.
Add and separate the liquids.

The ethyl acetate layer was washed with water, dried and concentrated to give an oily substance. The thus obtained oily substance was subjected to silica gel chromatography and eluted with a chloroform-duck-hexane mixture to obtain the target product λor as an oily substance.

Elemental analysis value: 01711101! F, Ni06 (molecular weight 467.20) OHN Theoretical value (X) 4171 137 [00 Experimental value (1) 4405 2.24 5.89 Next, in the general formula (1) obtained in this way, Representative examples of the compounds of the present invention are shown in Table 1. However, the present invention is not limited to these exemplified compounds, and the compound numbers in the table are also referred to in the following Examples and Test Examples. Ru.

In carrying out the present invention, a mixture of two or more of the compounds represented by the general formula (1) is mixed at a rate of 2.
0-2000? , preferably at a ratio of 100 to 10 GOf, but it goes without saying that the dosage can be adjusted depending on the circumstances of the actual situation.

When actually used, the compound of the present invention can be used directly as it is, but depending on the purpose of use, one or more compounds represented by the above general formula [1] may be dissolved in a liquid carrier. Alternatively, it can be dispersed, mixed with or adsorbed with a suitable solid carrier (eg diluent, filler, etc.), and if desired, an emulsifier 9 can be further dispersed therein.

The liquid carrier (solvent) mentioned here includes, for example, alcohols such as methyl alcohol, ethyl alcohol, and ethylene glycol, ketones such as acetone and methyl ethyl ketone, and ethers such as dioxane, tetrahydrofuran,
Cellsolve, etc., hydrogen hydrides such as benzene, toluene, xylene, hequinane, kerosene, kerosene, naphtha, methylnaphthalene, etc., esters such as ethyl acetate, butyl acetate, etc., organic bases such as pyridine, picoline, etc., dimethylformamide, acetonitrile, etc. These organic solvents are suitable, and one or a mixture of two or more of these may be used.

Examples of solid carriers (diluents, fillers, etc.) include mineral powders such as kaolin, bentonite, acid clay, clay,
Talc, diatomaceous earth, tributary powder, etc., vegetable powders such as soybean flour, wheat flour, wood flour, etc., as well as aluminum, activated carbon, etc. can be used, and one or a mixture of two or more of these can be used. .emulsifier.

Anionic, cationic, nonionic, and amphoteric surfactants can be used as dispersants, penetrants, and spreading agents.

9. Casein and gelatin, if desired.

Starch, sodium alginate, etc. can be used as adjuvants.

When formulating the compound of the present invention, the ratio of active ingredients can be set freely, but a content ratio of 5 to 90% is generally appropriate.

In addition, depending on the purpose of use, the compound of the present invention may be used with other herbicides,
It can be used in combination with fungicides, insecticides, plant growth regulators, fertilizers, etc.

Next, examples will be given to explain the compounds and carriers.

The adjuvant and the proportion used are not limited to those in this example.

In addition, the composition ratio of the components in this example shows parts by weight.

Example 1 (Irrigation agent) Compound No. I So part Sodium lignin sulfonate 1 part Diethylene alkylaryl ether in polio 4 parts Clay
45 parts These ingredients are mixed until homogeneous, ground, and used as an irrigation agent.

Example 2 (emulsion) Compound No. 4 20 parts Alkylbenzene sulfonate 3 parts Polyoxyethylene alkylaryl ether 10 parts Xytetrayl 67 parts These components were mixed until uniform, dissolved, and used as an emulsion. .

Example 3 (granules) Compound No. 6 6 parts Bentonite 30 parts Sodium alkyl sulfate 1.51! ! ! clay
62 parts 5 parts These ingredients are mixed until uniform, kneaded, and granulated using a conventional granulation method to be used as a granule.

Example 4 (Powder) Compound No. 5 7 parts Clay 93 parts These components are mixed until uniformly mixed and used as a powder.

The effects of the compounds of the present invention will be briefly explained using test examples.

Test example.

A 115,000 are polyethylene pot was filled with rice paddy soil (clay loam), seeds of Japanese field weed, Japanese cypress, and broad-leaved weeds were sown, and tubers of Japanese cypress and Japanese cypress were planted. At the same time, paddy rice at the two-leaf stage was planted at a depth of 2cI11.
The value per share was 3awK. At the same time as weed germination, weigh out a predetermined amount of the water use agent of each test compound prepared according to the formulation according to Example IK, dilute it in water in file H1 per bottle, and apply it to the water surface. The herbicidal effects and herbicidal effects on paddy rice were investigated after 3 weeks of cultivation. The numbers in the table indicate the herbicidal effects and the herbicidal effects on paddy rice, and the specific details are as follows.

Claims (1)

[Claims] (In the formula, Yl represents a halogen atom or a nitro group, and YI
The front of the Fi^rogen atom indicates a trifluoromethyl group,
The two companies, hydrogen atoms and halogen atoms, indicate the nitro fund.)
A diphenyl ether derivative represented by (2) The halogen atom t+ in the general formula represents a trifluoromethyl group, and 2
represents a hydrogen atom, a halogen atom, or a nido tetragroup) and a dicyclopylmethyl halide represented by the general formula (wherein X represents a halogen atom). A method for producing a Jirae product-lether 19 conductor represented by the general formula (wherein Yl # YM and 2 have the same meanings as above). Indicates a halogen atom or a trifluoromethyl group, 2
A herbicide characterized by containing one or more diphenyl ether derivatives represented by ) representing a hydrogen atom, a halogen atom, or a nitro group.