JPS597146A - N-(1-beta-naphthyl-isopropyl)phenylacetamide derivative, its preparation and herbicide containing the same - Google Patents

Abstract

NEW MATERIAL:The compound of formula I (R is H, halogen, 1-3C alkyl, 1- 3C alkoxy, or trifluoromethyl). USE:Herbicide suppressing the sprouting and growth of weeds, and selectively controlling especially perennial weeds. It exhibits excellent effect against the weeds of Cyperaceae family and Gramineae family. PROCESS:The compound of formula I can be prepared by reacting the phenylacetic acid derivative of formula II or its reactive derivative with 1-beta-naphthyl- isopropylamine of formula III for 0.5-2hr under heat refluxing. The herbicide of the present invention is prepared by mixing the compound of formula I with a liquid carrier such as organic solvent (e.g. benzene, ether, etc.) or a solid carrier such as mineral fine powder (e.g. siliceous earth, silicate, etc.), and is applied in the form of wettable powder, emulsifiable concentrate, granules, powder, etc.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel N-(/-β-naphthyl-isopropyl)phenylacetamide derivative, a method for producing the same, and a herbicide containing the same as an active ingredient.

Conventionally, various herbicides have been commercially available for use under flooded conditions such as rice cultivation, but they have drawbacks such as causing chemical damage to rice and having limited herbicide effect, mainly on annual weeds. Ta. For this reason, it is extremely difficult to control perennial weeds such as Japanese cypress, firefly, Japanese grasshopper, and black croaker, and countermeasures have become a major problem.

Therefore, it is desired to develop a herbicide that selectively controls these perennial weeds and does not cause any phytotoxicity to crops.

The present inventors have already succeeded in developing and proposed various herbicides that satisfy these objectives, but after further investigation, they discovered a new compound with excellent herbicidal effects and arrived at the present invention. .

The present invention represents a general formula (wherein R is hydrogen): loden, an alkyl group having 3 carbon atoms, an alkoxyl group having 3 carbon atoms, or a trifluoromethyl group. ), N-(/-β-naphthyl-inpropyl)phenylacetamide derivatives represented by the general formula (wherein, R is hydrogen), loden, an alkyl group having a carbon number of /-3, a carbon number / -3 represents an alkoxyl group or a trifluoromethyl group. ) or a reactive derivative thereof and /-β-naphthyl-isopropylamine represented by the formula The present invention provides a method for producing a naphthyl-4770 phenylacetamide derivative, and also provides a herbicide containing the compound of the general formula <I) as an active ingredient.

In the compound represented by the above general formula (1), R represents hydrogen, no-rodene, an alkyl group having /-3 carbon atoms, an alkoxyl group having /-3 carbon atoms, or a trifluoromethyl group, as described above, From the standpoint of herbicidal effects, hydrogen, chlorine, bromine, and fluorine.

Methyl, methoxyl and trifluoromethyl groups are preferred.

It should be noted that other substituents may be introduced into the compound represented by the above general formula (I) as long as they do not significantly affect the herbicidal effect contemplated by the present invention. Halocarne, alkyl group with carbon number/-3, alkoxyl group with carbon number/-3 as described in Japanese Patent No. 710633 can be used for nuclear substitution, and methyl at other positions can be used. An alkyl group having a carbon number of -3 and an alkoxyl group having a carbon number of -3 in order to substitute a group, hydrogen, etc.

It is possible to use an alkoxyalkyl group having a carbon number of λ-B, an allyl group, and the like.

The N-(/-β-naphthylinofOopyr)phenylacetamide derivative represented by the general formula (i) can be produced, for example, by the following method.

It is obtained by total reaction of the phenylacetic acid derivative represented by the general formula (II) or its reactive derivative with the /-β-naphthyl-inzolopylamine represented by the above formula (III), which is represented by the following formula. It will be done.

(If) (III) (1) (IJ) (III) (I) Specifically, phenylacetic acid or substituted phenylacetic acid is dissolved in methylene chloride, and /-β-naphthyl-isozolopylamine, trinoryl , marbutylamine and N-methyl-flood-chlorpyridinium iodide were added. It can be produced by heating under reflux for 2 hours. Another method is to add thionyl chloride to phenylacetic acid or substituted phenyl acetic acid chloride and heat under reflux for 1 hour to obtain phenyl acetic acid chloride or substituted phenyl acetic acid chloride. It can be produced by reacting -β-nanotyl-isozolopylamine and tri-n-butylamine under heating and reflux for o, s-, j hours.

Further, the obtained product can be isolated and purified by conventional washing operations or recrystallization.

The compound of the present invention is a novel compound, and is capable of suppressing the germination and growth of weeds, and particularly selectively controlling perennial weeds. In other words, if the soil is treated before and after flooding in direct-seeded rice cultivation in dry fields, the water worms will not cause any harm to the rice, and will eliminate weeds such as Cyperaceae, such as Cyperus spp. 7 exhibits outstanding herbicidal effects. However, when used as a soil treatment agent in transplanted paddy rice cultivation, it does not cause any harm to rice and can effectively control weeds of the Cyperaceae family and rice crops.

Furthermore, even when the herbicide of the present invention is used as a soil treatment agent for field crops such as broad-leaved crops, wheat, and corn, it controls Cyperaceae and Poaceae weeds without causing any harm to the crops. be able to.

The herbicide of the present invention can be used by mixing the compound as an active ingredient with a liquid carrier such as an organic solvent or a solid carrier such as fine mineral powder, and formulating it in the form of an aquarium, an emulsion, a 7-grain powder, etc. can. A surfactant may be added to impart emulsifying properties, dispersibility, spreading properties, etc. during formulation.

When the herbicide of the present invention is used in the form of an irrigation agent, usually "
10-45% by weight of the compound of the present invention in duplicate as active ingredient, qo-gg% by weight of solid carrier and 2-4% by weight of surfactant.
A composition may be prepared by blending them in a proportion of 5% by weight, and this may be used. When used in the form of an emulsion, the compound of the present invention is usually used in an amount of 20-30% by weight as an active ingredient, and a solvent β.
It may be prepared by mixing 5-75% by weight of the surfactant and 3-73% by weight of the surfactant. On the other hand, when used in the form of a powder, the compound of the present invention/-7 is usually used as the active ingredient.
It may be prepared by blending 5% by weight of solid carrier gO, 97% by weight of solid carrier gO, and 2-1% by weight of surfactant. Furthermore, when used in the form of granules, it may be prepared by blending 3-75% by weight of the compound of the present invention as the active ingredient, 95% by weight of the solid carrier gθ, and 95% by weight of the surfactant coater.

Here, fine mineral powder is used as the solid carrier, and examples of the fine mineral powder include diatomaceous earth, oxides such as slaked lime, phosphates such as apatite, sulfates such as Setsuko Tsu, talc, Examples include silicates such as pyroferrite, clay, kaolin, bentonite, acid clay, white carbon, quartz powder, and silica powder.

In addition, organic solvents are used as solvents, specifically aromatic hydrocarbons such as xylene, toluene, benzene, etc.
Chlorinated hydrocarbons such as chlorotoluene, trichloromethane, trichlorethylene, alcohols such as cyclohexanol, amyl alcohol, ethylene r IJ-t-l,
Examples include ketones such as isophorone, cyclohexanone, and cyclohexenyl-cyclohexanone, ethers such as butyl cellosolve, dimethyl ether, and methyl ethyl ether, esters such as inozolovir acetate, benzyl acetate, and methyl phthalate, amides such as dimethylformamide, or mixtures thereof. .

Further, as the surfactant, any of anionic, nonionic, cationic, and amphoteric ionic types (amino acids, betaine, etc.) can be used.

The herbicide of the present invention has no phytotoxicity to crops such as paddy rice, and is effective as a herbicide for use under flooded conditions such as in paddy rice cultivation, and particularly exhibits a selective control action against perennial weeds. The herbicide of the present invention can also be used in combination with other herbicides, growth regulators, pesticides such as insecticides, fungicides, fertilizers, and the like.

Next, examples of synthesis of the compound of the present invention and examples in which the compound was used as a herbicide are shown below.

Synthesis Example Millimoles of a given phenylacetic acid derivative S were dissolved in 30 ml of the salt ichmethylene, and added with /-β-wophthyl-i 7
-f ropiramin S mirimo
2 mmol of normal loop tylamine and 1 mmol of N-methyl-euchlorpyridinium iodide were added in this order, and the mixture was heated under reflux for an hour and then cooled to room temperature. Then, 2 times with 29 me of 5% aqueous hydrochloric acid.

Washed once with 1 Q ml of saturated saline solution and once with 1 Q ml of S% caustic sorter aqueous solution. Solvent: anhydrous sodium sulfate
After drying with Noumu Sg, the residue was distilled off under reduced pressure.

The precipitated crystals were collected from house to house, N-(/-β-nafti/L,
-iaflovir) phenylacetamide derivative was obtained, and this was recrystallized from ethanol to obtain a purified product.

The results are shown in Tables 1 and 2 together with the analysis results of purified products.

Table 1/Table 1/Table (Continued) Examples and Comparative Examples (1) Preparation of Herbicide 97 parts by weight of talc (trade name: Nidicrite) as a carrier, alkylaryl sulfonate (trade name: Neoperex) as a surfactant. , manufactured by Kao Atlas ■) and 5 parts by weight of a nonionic and anionic surfactant (trade name: Norpol 800A, manufactured by Toho Chemical Industry ■) were uniformly ground and mixed to form a carrier for wettable powders. I got it.

90 parts by weight of this hydrating agent carrier and N obtained in the above synthesis example.
- 70 weight of (/-β-naphthyl-isopropyl)phenylacetamide V derivative [- Uniformly ground and mixed to obtain a herbicidal wettable powder.

(2) Biological test results (flooded soil treatment test) ///Fill paddy soil into a 3300 are porcelain pot.
Seeds of Japanese wildflower, firefly, and Japanese cyperus were uniformly sown on the surface layer, and tubers of Japanese cyperus were transplanted. After flooding the box with water to the depth of the box, two paddy rice seedlings (variety Nihonbare) at the lambda leaf stage were transplanted.

Three days after transplanting the paddy rice, a predetermined amount of the diluted herbicide obtained in (1) above was dropped uniformly onto the water surface for treatment, and the plants were left in a Poratora greenhouse and watered at appropriate times.

Table 3 shows the results of investigating the herbicidal effect and phytotoxicity of paddy rice 20 days after the chemical solution treatment. In Table 3, the dosage is shown by the amount of active ingredient, and the paddy rice damage and herbicidal effect were measured in the air-dried form and expressed as follows.

Weeding effect θ vs. untreated plot 100%/
Otsu/-q9%2
2/-ro 0% 3//-20% q ro-
10%'@, 5/-3% 5 0% No phytotoxicity was observed in the herbicide of the present invention.

Table 3

Claims (1)

[Claims] 1. In the general formula (wherein R represents hydrogen, halo r, an alkyl group having carbon number/-3, an alkoxyl group having i/-3 carbon atoms, or a trifluoromethyl group). The represented N-(/-β-naphthyl-isozolopyl)phenylacetamide derivative. 2. R is hydrogen, chlorine, bromine, fluorine, or methyl group. The derivative according to claim 1, which is either a methoxyl group or a trifluoromethyl group. 3. General formula (in the formula, R is hydrogen), ron, an alkyl group having 1/-3 carbon atoms, an alkoxyl group having 1/-3 carbon atoms, or a trifluoromethyl group. ) or a reactive derivative thereof is reacted with /-β-naphthyl-isozolopylamine represented by the formula (wherein R is as defined above). ) N-(/-β-naphthyl-isopropyl)phenylacetamide. Method for producing derivatives. 4. The manufacturing method according to claim 3, wherein R2 in the general formulas (I) and (n) is hydrogen, chlorine, bromine, fluorine, a methyl group, a methoxyl group, or a trifluoromethyl group. 5.A reactive derivative of a compound represented by the general formula (11)--General formula (wherein R is hydrogen, halokene, an alkyl group having a carbon number of -3, an alkoxyl group having a carbon number of -3 or a 3. The method according to claim 3, wherein the acid chloride is an acid chloride represented by the formula (representing a fluoromethyl group). 6. R is hydrogen, chlorine, bromine, fluorine, or methyl group. The manufacturing method according to claim 3, which is either a methoxyl group or a trifluoromethyl group. 7 N-(/ - A herbicide containing a β-naphthyl-isopropyl) phenylacetamide derivative as an active ingredient. 8. R is hydrogen, chlorine, bromine, fluorine, or methyl group. The herbicide according to claim 7, which is either a methoxyl group or a trifluoromethyl group.