JPS5953466A - N-phenyltetrahydrophthalimide derivative, its preparation and herbicide containing said derivative as active component - Google Patents

Abstract

NEW MATERIAL:The compound of formula I [n is 0 or 1; A is group of formula IIor formula III (R is H, lower alkyl, lower alkenyl or lower alkoxycarbonylmethyl)]. EXAMPLE:N-[4-Chloro-2-fluoro-5-(1-hydroxyiminoethoxy)phenyl]-3, 4, 5, 6-tetrahydrophthalimide. USE:Herbicide having excellent herbicidal effect to the weeds in paddy field, plowed land, orchard, pasture, lawn, forestry, or uncultured land, and free from phytotoxicity to crops such as rice plant, corn, soybean, cotton, etc. PROCESS:The compound of formula I can be prepared, e.g. by reacting the halide of formula IV (X is Cl or Br) with N-(4-chloro-2-fluoro-5-hydroxyphenyl)-3,4,5,6- tetrahydrophthalimide in an inert solvent such as toluene in the presence of a base such as triethylamine at 70-100 deg.C.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a compound of the general formula [wherein n represents 0 or 1 and A represents 1k-OR 1 or -0-]. Here, R represents a hydrogen atom, a lower alkyl group, a lower alanyl group or a lower alkoxyalkylmethyl group. The present invention relates to an N-phenyltetrahydrophthalimide derivative (hereinafter referred to as the compound of the present invention) represented by the following formula, a method for producing the same, and a herbicide containing the same as an active ingredient.

The compounds of the present invention can be used to treat various weeds that are problematic in foliar and soil treatments in upland areas, such as freckle grass, snail knotweed, purslane, and white grass.

Bluetail (Bluetail), American hornwort, Ebisugusa, Japanese crocodile, American golden deer, field pansy, Nora carrot, Yaemura, American morning glory, + Ruba morning glory.

Broad-leafed weeds such as Convolvulus, Helicoptera, Potognathus, Prunus japonicus, Prunus japonicus, Prunus japonicum, Prunus spp., Japanese fir, sunflower, dogberry, corn marigold, and other broad-leaved weeds;
Poaceae weeds such as foxtail grass, blackgrass, sycamore, blackgrass, oat, and seiban sorghum, as well as weeds of the Asiatic family such as dayweed,
It has a herbicidal effect against weeds of the Cyperaceae family, such as Japanese perilla, and some of the compounds of the present invention
Wheat, rice.

It does not cause any harmful chemical damage to major crops such as soybean, cotton, and sugar beet.

Some of the compounds of the present invention can be applied to various weeds that are problematic in rice fields, such as grass weeds such as Japanese millet,
Broad-leafed weeds such as azalea, azalea, and chickweed, cypress, and firefly.

It has a herbicidal effect against weeds of the Cyperaceae family, such as Cyperaceae and Cyperus japonica, as well as paddy field weeds, such as Cyperus japonica, Prunus spp.

Therefore, the two compounds of the present invention are water F]1. It can be used as an active ingredient in herbicides for fields, orchards, pastures, lawns, forests, non-agricultural lands, etc.

The compound of the present invention has the general formula % formula % (1) [In the formula, X represents a chlorine atom or a bromine atom.

n and A have the same meaning as above. ] The halide represented by in an active solvent,
Potassium carbonate, sodium carbonate, triethylamine.

It can be produced by reacting at 70 to 100'C in the presence of a J group such as pyridine.

Matco 9 The compound of the present invention has the general formula [wherein n has the same meaning as above. ] and the general formula fLNOR(IV) [wherein R represents a hydrogen atom, a lower alkyl group, a lower alekenyl group, or a lower alkoxycarbonylmethysyl group]. ] It can be produced by reacting an alkoxyamine represented by the following or a salt thereof in a medium such as 1-tanol, tetrahydrofuran, or water.

The raw material compound N-(4-chloro-2-fluoro-5
-Hydroxyphenyl-8,4,5°6-tetrahydrophthalimide can be produced from 2-chloro-4-fluorophenol according to the reaction route shown below.

(V) ()'I) (Vlt)
(Vial) (IX) That is, phenol (Vll
l) ft: Reduced to aniline ([1), which when reacted with 'a> 3,4,5,6-titrahydrophthalic anhydride yields N-(4-chloro-2-fluoro-5- hydroxyphenyl)-3゜4.5.6-titrahydrophtha? Reimide is obtained.

Next, production examples of two compounds of the present invention will be shown.

Production Example 1 Imethylhydroxamotal chloride 2. Triethylamine 2f, N-(4-chloro-2-771/oli-5-hydroxyphenyl)-3,4,5,6- was added to a solution of relene (20 t) containing Of at -40 to -80'C. Titrahydrophthalide 4.5y'r: Addition 1. ．． -70～-
Stirred at 20'C for 8 hours.

Add reaction solution IC9 water and add toluene.1. Ta. Wash the torueso layer with water at the saturation point in Mizusawa, dry it,
It's dark and dark. The residue was purified using silica gel column chromatography to obtain N-(-4-chloro-2-)! 1/
Oro 5-(1-1-droxyiminoethoxy)phenyl: l3,4,5, (i-tetrahydrophthalimide 2.7) was obtained. .

ITID 181-13]-5'('.

NMRδ (ppnl > 1.8 (4 horses 1n L
1.9 (8H, s).

2-45 (4H-r tn ) -'1.05 (I
Hld, J=6H2), 7.8 (group, d,
J=10H2)7.33 (I H5s, -0j1.
-) Production Example 2 N-(4-chloro-2-fluoro-5-(2-oxopropoxy)phenyl) -8,4,5,6-tetrahydrophthalimide1. Pyridine 0.5f and hydroxylamine hydrochloride 0.85 dissolved in ry+ethanol 10*t
Add F and stir at room temperature for 2 hours. Add water, extract with ether, and extract the ether layer.

Washed with dilute hydrochloric acid, further washed with water, dried and concentrated to give glassy N-(4-chloro-2-fluoro-5-(2-hydroxyiminopropoxy)phenyl)-3,4,5,6-tetrahydrophthalimide 0. Get 4f.

NMRε, ppm (CDC7-) 2.0 (8 horses s
) # 4.5 (21(.

s), 6.8 (IH, d).

7.25(114,d) Some of the compounds of the present invention that can be produced by such a production method are shown in Table gQ'+1.

Table 1: 9 when the compound of the present invention is used as an active ingredient of a herbicide
It is usually mixed with a solid carrier, a liquid carrier, a surfactant, and other formulation auxiliaries to formulate C1 emulsions, wettable powders, suspensions, and the like.

These preparations contain the compound of the present invention as an active ingredient in a weight ratio of 0.5 to 95%, preferably 1 to 8096.

The solid carrier may include fine powders or granules such as kaolin clay, acpargite clay, bentonite, acid clay, pyrophyllite, talc, diatomaceous earth, calcite, limestone powder, urea, ammonium sulfate, and synthetic hydrous silicon oxide. Liquid carriers include aromatic hydrocarbons such as xylene and methylnaphthalene, alcohols such as isopropanol, ethylene glycol, and cellosolve, and acetone.

Surfactants used for emulsification, dispersion, wet carbon, etc. include gamma ton such as cyclohexanone and isophorone, vegetable oils such as soybean oil and cottonseed oil, dimethylene resul yF, KiE/do, acetonitrile, etc. Alkyl sulfate base, Alkyl (aryl) sulfonate, dialkyl sulfosuccinate, polyoxyethylene alkylaryl ether phosphate J [J
and nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, polyoxyethylene polyoxypropylene block copolymer, sorbitan fatty acid ester, and polyoxysorbitan fatty acid ester. Adjuvant IC for formulation is lignin sulfonate, alginate.

Examples include polyvinyl alcohol, gum arabic, CMC (carboxymethyl cellulose), and AP (isopropyl acid phosphate).

Examples of formulations are shown below. The compounds of the present invention are indicated by compound numbers in Table 1. Parts represent 11 parts by weight.

Formulation Example 1 1.50 parts of Invention B, 3 parts of calcium lignosulfonate, 2 parts of sodium lauryl sulfate, and 45 parts of synthetic hydrous silicon oxide are thoroughly ground and mixed to obtain a wettable powder.

Formulation Example 2 4, 1 part of the compound of the present invention, 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate, 30 parts of xylene, and isopolone t4
Mix 0 parts well to obtain an emulsion.

Formulation Example 8 9.2 parts of the compound of the present invention, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65 parts of kaolin clay were thoroughly ground and mixed, and water was added to mix well.

Granulate and dry to obtain granules.

Formulation Example 4 6.25 parts of the compound of the present invention, part a of polyoxyethylene sorbitan monooleate, part CMCa.

A suspension is obtained by mixing 69 parts of water and wet milling until the particle size of the active ingredient is below %i microns.

These preparations can be used as is or diluted with water, etc., and treated with foliage or soil. In the case of soil texture, the preparation can be applied to the soil surface (if necessary, mixed with the soil after application) or irrigated into the soil.

Furthermore, by mixing it with a pond herbicide, 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 0.051 to 509.
Preferably, it is 0.159 to 20y, and emulsions, wettable powders, suspensions, etc. are mixed with 1 liter to 10 liters of water (if necessary, a spreading aid such as a spreading agent is added) per 1 are. When applied diluted, do not dilute single granules, etc.f,r
<That J is applied. In addition to the above-mentioned surfactants, the spreading agent includes polyoxyethylene resin acid, lignin sulfonate, abietate, and the like.

Next, test examples will show that the nine compounds of the present invention are useful as active ingredients of herbicides. The nine compounds of the present invention are shown by the compound numbers in Table 1, and the compounds used for comparison are shown by the compound numbers in Table 2.

Table 2 Also, what is the herbicidal effect on violets and crops?

The degree of inhibition of germination and growth of the test plants during the survey was observed with the naked eye, and those that were not aged or had little difference from those in which no compound was tested were given a score of 0, and the test plants withered or completely stopped growing. The number of things that are inhibited is set as 5, and the range is 0 to 5.
It was evaluated on a 6-level scale of 5 and indicated as *0-1, 2*8t L5.

Test example! Field soil m physical test surface q 3 :d X 2 B cd , depth 1lcIl
The field [(-111 wo km, Saban sorghum, oats.

Sow crabgrass, Japanese velvet, mulva morning glory, golden deer, dogberry and buckwheat vine, 1-2 c.
Cover with soil to a thickness of 1.25 oz. The test compound was added to Formulation Example 21 to form an emulsion Iζ, and the predetermined amount was 10% per are.
Dilute with a liter of water.

After spraying on the surface of the soil with a small sprayer, it was sprayed to a depth of 4 at.
Thoroughly mix the surface layer of the soil. moreover.

1. Seeds of Kumorokoji, wheat, cotton and soybean 2.
It was embedded in the tl of C11. After spraying, the plants were grown in a greenhouse for 20 days and their herbicidal efficacy was investigated. The results are shown in Table 3.

Test Example 2 Field soil stem and leaf treatment test A vat with an area of 38 x 23 cj and a depth of 1101 cm was filled with field soil and treated with corn, wheat, hackberry, sugar beet, cotton, soybean, American staghorn, Japanese fir,
Japanese crocodile, Japanese morning glory, Japanese dogfish, and Japanese dogfish were sown and grown for 18 days. Thereafter, the test compound made into an emulsion according to Formulation Example 2 was diluted with water equivalent to 5 liters per are containing a spreading agent, and the specified amount was sprayed from the back of the plant to the entire stem and leaf area using a small sprayer. Spread evenly
Ko. At this time, the growth status of each plant differs depending on the grass type, but it is in the 1 to 4 leaf stage and the grass history is 2 to 12 cIII.

The herbicidal efficacy was investigated 20 days after spraying. The result is the fourth
Shown in the table. The nine tests were conducted in a greenhouse throughout the entire period.

Test example 3 Paddy soil and foliage treatment test 1 / 50
(A 10A Wagner pot was filled with paddy soil, and Japanese millet, broad-leaved weeds (Azeena, Aspergillus japonica, Chickweed), bulrush seeds, and overwintering buds of Pinus elegans were mixed in at a depth of 1 to 2α.

After flooding and making the water mouth 1 state, add 1 to 2 tubers of Urikawa.
The rice was buried at a depth of 1, and then rice at the 8-leaf stage was transplanted and grown in a greenhouse. After 4 days (the beginning of each weed's emergence), a predetermined amount of the test compound made into an emulsion according to Formulation Example 2 was diluted with water equivalent to 10 milliliters per pot, and the solution was dropped onto the water surface. , : .

We then grew them in a greenhouse for 20 days and investigated their herbicidal efficacy.
Ko. The results are shown in Table 8.

Table 8

Claims (1)

[Claims] (1) General formula) or -〇-. Here, R represents a hydrogen atom, a lower alkyl group, a lower alkenyl group or a lower alkoxycarbonylmethyl group. ] N-phenyltetrahydrophthalimide derivative. 12) Represents the general formula % formula %. Here, R is a hydrogen atom, a lower alkyl group,
Represents a lower alkenyl group or lower alkoxycarbonylmethyl group. [In the formula, n and A have the same meaning as above. ] A method for producing an N-phenyltetrahydrophthalimide derivative. (8) General formula F 0 1 [where n 1. t represents O or l, A is -C-
-OR Represents 1 or -C-. Here, R represents a hydrogen atom, a lower alkyl group, a lower alkyl group, =, or a lower alkoxycarbonylmethyl group. ] An eye-removal agent characterized by containing an N-phenyltetrahydrophthalimide derivative as an active ingredient.