JPS63264571A - Pyridyl-2-oxy-phenoxy-propionic acid amide derivative - Google Patents

Abstract

NEW MATERIAL:A pyridyl-2-oxy-phenoxy-propionic acid amide derivative of formula I (X is H, Cl; R is H, Cl, methyl, methoxy). EXAMPLE:N-Cyano-N-phenyl-2-[4-(3-chloro-5-trifluoromethyl-2-pyridyloxy )-pheno xy]propinamide. USE:Herbicide: it shows good selectivity to beans, cotton, carrot, potato, beet, cabbage, mustard, mustard plant, ground nuts, radish, tobacco, tomato, cucumber, etc. It causes no chemical injury on application with usual concentration. PREPARATION:For example, a compound of formula II (Hal is halogen) is allowed to react with another compound of formula III to give the compound of formula I.

Description

DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a novel pyridyl-2-oxy-phenoxy-propionic acid amide derivative, a method for producing the same, and a selective herbicide containing the compound as an active ingredient.

BACKGROUND OF THE INVENTION It has been reported that a large number of phenoxypropionic acid ester derivatives have herbicidal activity.

For example, Li'2-C4-(4-toIJfluoromethylphenoxy)phenoxy]propionic acid methyl ester 2-(4-(2,4-dichlorophenoxy)phenoxy)propionic acid methyl ester, 2-(4-(3 ,5
-dichloro-2-pyridyloxy)phenoxy]propionate methylesterenope 2-C4-(5-)lifluoromethyl-2-pyridyloxy)phenoxy]propionate butyl ester is known and used for weed control. There is. However, the effectiveness of these substances is not always sufficient.

[Problem that the invention seeks to solve]

Beet, soybean, cotton, alfalfa, rapeseed, potato,
In the cultivation of broad-leaved crops such as sunflowers, radish, Chinese cabbage, cabbage, and tomatoes, without harming these useful crops,
There is still a strong market demand for a selective herbicide that can kill regular weeds using either pre-emergence soil treatment or post-emergence foliage treatment, even though many herbicides have already been developed and sold. . In particular, when foliage treatment is performed after weed emergence, the conventional phenoxypropionate esters described above take more than 8 days to achieve post-treatment effects, which has caused many dissatisfaction among crop growers. It was strongly desired.

The object of the present invention is to obtain said compounds industrially and to provide even more improved selective herbicides that meet the needs of the market.

[Means and effects for solving the problems] The present invention has the following general formula [1] (wherein, X represents a hydrogen atom or a chlorine atom, and R represents a hydrogen atom, a chlorine atom, a methyl group, or a methoxy group). The present invention provides a propionic acid amide derivative represented by the formula (hereinafter referred to as the compound of the present invention) and a herbicide containing the compound of the present invention as an active ingredient. .

The compound of the present invention can be produced by various methods, but
A typical manufacturing method is shown by the reaction formula below.

However, in the formula, X and R represent the same meanings as above, and Hal
represents a halogen atom.

These reactions are carried out in the presence or absence of a reaction solvent.
The compounds of the present invention are obtained by using a suitable base.

Reaction solvents include ketones such as acetone and methyl ethyl ketone, aromatic hydrocarbons such as benzene, toluene, and xylene, ethers such as ethyl ether, tetrahydrofuran, and dioxane, and halogenated compounds such as chlorobenzene, chloroform, carbon tetrachloride, and dichloroethane. Hydrocarbons, tertiary amines such as triethylamine, pyridine, and dimethylaniline, and polar solvents such as acetonitrile, dimethylformamide, dimethyl sulfoxide, and hexamethyl phosphoric acid IJ amide are used.

As a base, triethylamine, pyridine, 1.8-
diazabicyclo-(5,4,0)-7-undecene,
Tertiary amines such as dimethylaniline, alkali hydroxides such as sodium hydroxide and potassium hydroxide, alkaline earth hydroxides such as calcium hydroxide, alkali carbonates such as sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc. Salts and metal hydrides such as sodium hydride are used. The reaction usually proceeds at a reaction temperature of about 150°C to about 150°C, preferably about 0°C to about 100°C, and the reaction time is about several minutes to about 48 hours.

Representative examples of the compounds of the present invention are shown in Table 1 below, but the present invention is not limited only to these compounds.

1st Table I Cjl! Hn251.574
02 H4-CH3mp 112-11
4℃3H3-Ctl, mp
89-91.5℃4 H20CH3mp
115-117℃5 H3-OCf
13n251.55936 H4-4-0
CH3104~106℃7 HHmp10
3～104℃8 Cj! 2-Cjl
! n251.55509 C1!
3-C1n251.566510 C1
4-Cj2 mp 95-97°C When the compound of the present invention is used as a herbicide, it can be prepared using methods commonly used in agricultural chemical formulations using agricultural chemical adjuvants, such as emulsions, wettable powders, aqueous solutions, oil solutions, etc. It can be used in the form of preparations such as powders and granules. In actual use, these various preparations can be used as they are or diluted with water to a predetermined concentration.

Specific examples of pesticide adjuvants include diluents, surfactants, stabilizers, sticking agents, aerosol propellants, and synergists. Solvents used as diluents include water, organic solvents, hydrocarbons, halogenated hydrocarbons, alcohols, ethers, alcohol ethers, ketones,
Examples include esters, amides, and sulfoxides.

In addition, fillers and solid carriers include inorganic powder and granules such as slaked lime, magnesium lime, gypsum, calcium carbonate, ridged earth, perlite, pumice, diatomaceous earth, alumina, zeolite,
Examples include clay minerals (talc, vermiculite, kaolinite), vegetable powder (for example, starch, grain, glucose, etc.), synthetic resin powder (for example, phenol resin, carbon resin, vinyl chloride (fat), etc.) Examples of surfactants include anionic surfactants (for example, alkyl sulfates, arylsulfonic acids, succinates, polyethylene glycol alkylaryl ether sulfate salts), cationic surfactants (for example, alkyl amines,
Examples include polyoxyethylene alkyl amines), nonionic surfactants (for example, polyoxyethylene glycol ethers, polyoxyethylene glycol esters, polyhydric alcohol esters), and amphoteric surfactants. Other examples include stabilizers, fixing agents, efficacy extenders, dispersion stabilizers, and synergists.

The amount of the compound of the present invention used as an active ingredient can be appropriately changed depending on the form of the preparation, the method of application, purpose, timing, weed growth status, etc.

When generally used, the amount is 0.05 to 10 kg/ha, preferably 0.1 to 5 kg/ha.

〔Example〕

EXAMPLES Next, the present invention will be specifically described with reference to Examples, but the present invention is not limited to these Examples.

Example 1 N-cyano-N-phenyl-2-C4-(3-chloro-
Synthesis of 5-trifluoromethyl-2-pyridyloxy)-phenoxy]propionamide (compound No. l) 2-C4-(3-chloro-5-trifluoromethyl-2
1.62 g of -pyridyloxy)-phenoxy]propionic acid chloride was dissolved in 10 ml of dichloromethane, and this was added dropwise at room temperature to a dichloromethane solution containing 0.51 g of N-cyanoaniline and 0.44 g of triethylamine. After stirring the reaction mixture at room temperature for 6 hours, ice was added and the dichloromethane layer was separated. The dichloromethane layer was washed with dilute hydrochloric acid and water in that order, and then dried using anhydrous magnesium sulfate. The drying agent was removed and dichloromethane was distilled off. The obtained residue was subjected to column chromatography [silicagenopebenzene/ethyl acetate = 10/1 (V/V)]
] to obtain 0.7 g of the target product (n2J, 574
0) was obtained.

Example 2 Synthesis of N-cyano-N-phenyl-2-C4-(5-trifluoromethyl-2-pyridyloxy)-phenoxy]propionamide (compound No. 7) 2-C4-
<5-) 1.54 g of reflow methyl-2-bilylyloxy)-phenoxy]propionic acid chloride was dissolved in 10 m12 of dichloromethane, and this was added to a dichloromethane solution containing 0.6 g of N-cyanoaniline and 0.51 g of triethylamine in 30 mf+ at room temperature. dripped. After stirring the reaction mixture at room temperature for 6 hours, water was added and the dichloromethane layer was separated.

The dichloromethane layer was washed with dilute hydrochloric acid and water in that order, and then dried using anhydrous magnesium sulfate. The drying agent was removed and dichloromethane was distilled off. The obtained residue was subjected to column chromatography [silicagenopebenzene/ethyl acetate = 1
0/1 (Developed with V/V>) to obtain the target product 1.
26 g (mpl 03-104°C) was obtained.

Example 3 Preparation of emulsion 20 parts of the present compound Nα1 (parts indicate parts by weight, the same applies hereinafter), 60 parts of xylene, and Tsurpol 2806B.
(Product name: Surfactant manufactured by Toho Chemical Industries) 20 parts were uniformly stirred and mixed to form an emulsion.

Example 4 Production of a wettable powder 10 parts of white carbon, 65 parts of Zeekrite, 5 parts of Tsurupol 5039 (trade name: surfactant manufactured by Toho Chemical Industries), and 20 parts of the present compound No. 10 were mixed and ground. It was used as a hydrating agent.

Example 5 Stalk and foliage treatment test Fill a 22cm x 16cm plastic vat with field soil, sow a certain amount of soybean, beet, rice, wheat, corn, and oat seeds, and then weeds such as crabgrass, wild grass, knotweed, chickweed, and white locust. soil containing seeds of approx.
It was covered with soil to a thickness of cm. When the gramineous plants reached the 3.0 to 3.5 leaf stage, a prescribed chemical was uniformly sprayed on the foliage. The growth status of the converted bacteria was observed 14 days after the drug treatment, and the results shown in Table 2 were obtained. The numerical value of the degree of growth inhibition was divided into five levels from 5 to 1 (5 indicates complete withering, 1 indicates no effect at all).

〔Effect of the invention〕

The compound of the present invention has good selectivity for cultivated plants such as beans, cotton, carrot, potato, beet, citrus, mustard, mustard, peanut, radish, tobacco, tomato, cucumber, etc. Weeds, especially weeds of the genus family, such as quince, porphyry, porphyry,
When pre-emergent soil treatment and post-emergent foliage treatment are applied to foxtail grass, wild oat, sparrow gnome, goldenrod, grasshopper, staghorn grass, staghorn grass, johnson grass, etc., it exhibits excellent selective control effects.

Claims (2)

[Claims] (1) General formula [I] ▲Mathematical formulas, chemical formulas, tables, etc.▼[I] (In the formula, X represents a hydrogen atom or a chlorine atom, and R represents a hydrogen atom, a chlorine atom, a methyl group, or a methoxy group) pyridyl-2-oxy-, which is represented by
Phenoxy-propionic acid amide derivative. (2) General formula [I] ▲Mathematical formulas, chemical formulas, tables, etc.▼[I] (In the formula, X represents a hydrogen atom or a chlorine atom, and R represents a hydrogen atom, a chlorine atom, a methyl group, or a methoxy group) A herbicide characterized by containing a pyridyl-2-oxy-phenoxy-propionic acid amide derivative represented by the following as an active ingredient.