JPS5967255A - N-phenyltetrahydrophthalamic acid derivative, its preparation and herbicide containing said derivative as active component - Google Patents

Abstract

NEW MATERIAL:The compound of formula I (R is lower alkyl, lower alkenyl, lower alkynyl,or lower alkoxycarbonylmethyl; X is halogen). EXAMPLE:N-2-Fluoro-4-chloro-5-methoxyphenyltetrahydrophthalamic acid. USE:A herbicide exhibiting excellent herbicidal activity against broad-leaved weeds, gramineous weeds, cyperaceous weeds, etc., and has no phytotoxicity to corn, soybean, etc. PROCESS:The compound of formula I can be prepared by reacting the aniline derivative of formula II with 1-1.2 equivalent of 3,4,5,6-tetrahydrophthalic anhydride in a solvent such as hexane, benzene, chloroform, etc. at 0-60 deg.C for 30min-20hr.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention is based on the general formula [wherein R represents a lower alkyl group, lower alkenyl group, lower alkynyl group or lower alkoxycarbonylmethyl group, and X represents a halogen atom]. ] The present invention relates to the N-phenyltetrahydrophthalamic acid derivative (hereinafter referred to as the compound of the present invention) shown in the following, a method for producing the same, and a herbicide containing the same as an active ingredient.

The compound of the present invention can be used to treat weeds that cause problems in thatch treatment and soil treatment in fields, such as freckle weeds, snail knotweed, sperihus, chickweed, whiteweed, blueberry, Japanese radish, white chestnut, shepherd's purse, American hornwort, Japanese crocodile, and other weeds. Poaceae weeds such as American golden deer, American morning glory, Maruba morning glory, European morning glory, Japanese grasshopper, Japanese dogfish, broad-leaved weeds such as Japanese grasshopper, Japanese barnyard grass, blackberry grass, foxtail grass, oat, oat, Seiban sorghum, etc. The compound of the present invention has a herbicidal effect against cyperus weeds and the like, and does not cause any harmful effects on mature crops such as corn and soybean.

In addition, the compound of the present invention can be applied to various weeds that are a problem in rice fields, such as grasses, broad-leaved weeds such as Japanese millet, broad-leaved weeds such as azalea, cypress, and chickweed;
It has a herbicidal effect on paddy fields such as Urikawa, and does not cause any harmful effects on rice.

The compound of the present invention can be used in rice fields, upland fields, 1 to 1 fruit trees,
) It can be used as an active ingredient in herbicides for lawns, forests, or non-agricultural lands.

The compound of the present invention has the general formula [wherein R and X have the same meanings as above]. ] The aniline conductor shown by /~/0.2 Anhydrous 3
,4. t, O-tetrahydrophtha JItp and θ in a solvent.
It can be produced by reacting at °C to 6θ°C1θ, S time to -0 hours.

Solvents include hexane, heptane, ligroin, aliphatic hydrocarbons such as petroleum ether, aromatic hydrocarbons such as benzene, toluene, and xylene, chloroform, carbon tetrachloride,
Halogenated hydrocarbons such as dichloroethane, chlorobenzene, dichlorobenzene, ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, diethylene glycol dimethyl ether, etc., ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone, cyclohexanone, etc. , esters such as ethyl formate, ethyl acetate, butyl acetate, and diethyl carbonate, nitrites such as nitroethane and nitrobenzene, nitriles such as acetonitrile and isobutyronitrile, pyridine, triethylamine, N,
Tertiary amines such as N-diethylaniline, tributylamine, N-methylmorpholine, formamide, N,N
- Acid amides such as dimethylformamide and acetamide, dimethyl sulfoxide, sulfolane, etc., compounds, etc., and mixtures thereof.

After the reaction is completed, the product is subjected to conventional processing and, if necessary, purified by chromatography, distillation, recrystallization, etc.

Next, an example of the production of the "unexploded 1" compound will be shown.

Production example/ (Excretion of the compound of the present invention/) Cofluorocouchlororo j-methoxyaniline/,
Zano and Anhydrous 3. 3-1 O-tetrahydrophthalic acid/
. Acetone for S! The mixture was stirred at θ°C for 2 hours in Oml.

Concentrate under reduced pressure, filter, wash the crystals with a small amount of ether, and
-,2-Fluoro-guchloro-5-methoxyphenyltetrahydrophthalami: 'ti93.3y was obtained□
Some of the compounds of the present invention that can be produced by the production method such as rrb p, //I ~/, 2θ° are
4 on the table.

Table 1 General formula % Formula % When using the compound of the present invention as an active ingredient of a herbicide,
It is usually mixed with solid carriers, liquid carriers, surfactants, and other formulation auxiliaries to formulate emulsions, aqueous solutions, suspensions, granules, etc.

These preparations preferably contain the compound of the present invention as an active ingredient in an amount of 6.7 to 25% by weight, preferably in an amount of 1/~.

Solid carriers include fine powders or granules such as kaolin clay, attapulgite clay, bentonite, acid clay, pyrophyllite, talc, diatom+, calcite, walnut powder, urea, ammonium chloride, and synthetic hydrous silicon oxide. Liquid carriers include aromatic hydrocarbons such as xylene and methylnaphthalene, alcohols such as isopropanol, ethylene glycol, and cellosolve, ketones such as acetone, cyclohexanone, and isophorone, vegetable oils such as soybean oil and cottonseed oil, and dimethyl Examples include sulfoxide, acetonitrile, water, etc.

Surfactants used for emulsification, dispersion, wet carbonization, etc. include alkyl sulfate salts, alkyl (aryl) sulfonate salts, dialkyl sulfosuccinate salts, polyoxyethylene alkylaryl ether sulfate salts, etc. Anionic surfactant, polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether,
Examples include nonionic surfactants such as polyoxyethylene polyoxybrobylene block copolymer, sorbitan fatty acid ester, and polyoxysorbitan fatty acid ester.

Formulation auxiliaries include lignin sulfonate, alginic acid group, polyvinyl alcohol, gum arabic, CMC (carboxymethyl cellulose), PAP (isopropyl acid phosphate), and the like.

Examples of formulations are shown below. In addition, the compounds of the present invention are indicated by the compound fragrance names in Table 7. The parts are shown as overlapping parts.

Formulation Example: 50 parts of the compound of the present invention, 3 parts of calcium lignin sulfonate, 5 parts of sodium lauryl chloride acid, and 5 parts of synthetic hydrous silicon oxide+ are thoroughly ground and mixed to obtain an irrigation agent.

Formulation Example 2 72 parts of the compound of the present invention, 4 parts of polyoxyethylene styryl phenyl ether, 1 part of calcium dodecylbenzenesulfonate, 30 parts of xylene and 72,170 parts of cyclohexane are thoroughly mixed to obtain an emulsion.

Formulation Example 3 2.3 parts of the compound of the present invention, synthetic hydrated silicon oxide/synthesis,
Calcium lignin sulfonate I\, 30 parts bentonite and kaolin clay, 4. After thoroughly grinding and mixing the ff part, adding water and mixing well, granulate and dry to form granules.

Formulation Example Compound 31 of the present invention. ．． 2.5 parts of polyoxyethylene sorbitan monooleate, 3 parts of 0M0, and 6 parts of water are mixed and wet-milled until the particle size of the active ingredient is less than 1S micron to obtain a suspension.

These preparations are directly diluted with irrigation water, etc., and treated with foliage or soil.

For soil treatment, the preparation can be sprayed on the soil surface (if necessary, mixed with the soil after spraying) or sprinkled over the soil.

Furthermore, by mixing it with other herbicides, it can be expected to increase the herbicidal efficacy. Furthermore, it can be used in combination with insecticides, acaricides, nematicides, fungicides, plant growth regulators, fertilizers, soil conditioners, and the like.

When the compound of the present invention is used as an active ingredient of a herbicide, the application rate is usually /y to /θθy1 per are, preferably 2f/-409, and emulsions, irrigation agents, suspensions, etc. are per liter/are. It is diluted with ~/θ liter of water (in the case of polished products, a spreading aid such as a spreading agent is added) and applied, and the granule cap is applied as is without any dilution.

Spreading agents include, in addition to the above-mentioned surfactants, polyoxyethylene resin acids (esters), lignin sulfonates, abietin 11 salts, dinaphthylmethane disulfonates, paraffins, and the like.

Next, test examples will show that the compounds of the present invention are useful as active ingredients of herbicides. The compounds of the present invention are indicated by the compound numbers in Table 1, and the compounds used for comparison are indicated by the compound symbols in Table 3.

Table 1 also shows the herbicidal efficacy against weeds and crops (d). If the test plant is not present, it is ``θ'', and if the test plant has died or its growth has been reduced to the original condition, it is evaluated as rJJ. show.

Test Example/Upland Soil Mixture Treatment Test A cylindrical plastic pot with a diameter of 70 m and a depth of 70 m was filled with upland soil and sown with barnyard millet, Japanese cabbage (//), blueberry, Japanese yam, and corn, and seeded with seeds. Dilute the test compound in an emulsion with water equivalent to /are/θ liter according to the formulation example, and spray the specified amount on the soil surface with a small sprayer, and then spray the soil surface to a depth of 1 cm. Mixed well. After spraying, the herbicidal efficacy was investigated in a greenhouse for -θ days. The results are shown in Table 3.

Table 3 (/, 2) Test example Field field stem and leaf treatment test Fill a cylindrical plastic pot with a diameter of 70 m and a depth of 70 m with field soil, sow barnyard grass, Japanese morning glory, Japanese radish, Japanese radish, and Japanese daikon radish. It was grown for days. Thereafter, the test compound made into an emulsion according to Formulation Example C was diluted with water containing a spreading agent equivalent to /A/θ liter,
A small I! The foliage was sprayed from above the plant using a JI' fogger. After spraying, the plants were grown in a greenhouse for 2θ days and their herbicidal efficacy was investigated. The results are shown in Table 9.

Active ingredient Herbicidal efficacy Application amount Compound (y/a) Millet Wrist radish Daikon Ichibi Dice/ /θ
jj, ff-33! J! / /l/ 41 S j j here s,,1sssi 5. 5J, 5.5-g note, 5'', 3jJj/Test Example 3
Paddy soil execution test A cylindrical plastic pot with a diameter gcrn and a % depth of 72 cm was filled with paddy soil, and seeds of Japanese millet and broad-leaved weeds (Azaena, Azalea, Chickweed) were mixed in at a depth of 7 to 2 cm. After watering the rice fields and making them into paddy fields, tubers of Urikawa were buried at a depth of ~2cm, and then single-leaf rice was transplanted and grown in a greenhouse. Formulation example after one day (early stage of emergence of each weed)! The test compound made into an emulsion according to the method was poured into 7 pots with S milliliters of water, and the titer was added to the water surface.

The rhyme and the lower ridge were confirmed within θ days, and the weeding effect was confirmed. The results are shown in Figure J.

(/j complete)

Claims (1)

[Scope of Claims] (1) General formula % Formula % [In the formula, R represents a lower alkyl group, a lower alkenyl group, a lower alkynyl group or a lower alkoxycarbonylmethyl group, and x represents a halogen atom. ] An N-phenyltetrahydrophthalamic acid conductor represented by: (Incorporated) General Formula [In the formula, R represents a lower alkyl group, a lower alkenyl group, a lower alkynyl group, or a lower alkoxycarbonylmethyl group, and X represents a halogen atom. ] The aniline derivative represented by and anhydride 3,4. t. General formula % characterized by reacting with O-tetrahydrophthalic acid [In the formula, R and X represent the same meanings as above. ] A method for producing an N-phenyltetrahydrophthalamic acid derivative. (3) In the general formula til group, X represents a halogen atom. ]
- A herbicide characterized by containing a phenyltetrahydrophthalamic acid derivative as an active ingredient.