JPS6140277A - 3-(substituted phenyl)-5-alkyl-1,3,4-oxazolin-2-one compound and herbicide containing said compound as active component - Google Patents

Abstract

NEW MATERIAL:The 3-(substituted phenyl)-5-alkyl-1,3,4-oxadiazolin-2-one compound of formula I [X and Y are halogen; R<1> is alkyl; R<2> is alkyl, alkenyl, alkynyl, alkoxyalkyl or group of formula II (R<3> is H or alkyl); A is OR<4> or group of formula III (R<4> is alkyl; R<5> and R<6> are H or alkyl)]. EXAMPLE:5-t-Butyl-3-[4-chloro-5-[1-( ethoxycarbonyl )propylthio]-2-fluorophenyl]- 1,3,4-oxazolin-2-one. USE:Useful as a selective herbicide. It has high herbicidal activity even to intractable weeds such as wild morning-glory, bulrush, etc., and has high safety to crops. PREPARATION:The compound of formula I can be prepared by reacting the hydrazide derivative of formula IV with phosgene or trichloromethyl chlorocarbonate at -30-+160 deg.C.

Description

[Detailed Description of the Invention] [Industrial Application Field] The present invention provides novel j-(substituted phenyl)-! -Alkyl/, J, II-oxazoline-coons and herbicides containing the same as an active ingredient.

[Prior art]

certain 3-(substituted phenyl)-&-alkyl/,
It is known that e-oxazoline coions have herbicidal activity, for example,
No. 791, tit. 3- (J.

Goodichlor-3-inpropoxyphenyl)-5-t
-butyl-/, J, daoxazolin-one is written.

[Problem that the invention seeks to solve]

The present inventors aimed to obtain a herbicide with higher herbicidal activity and less phytotoxicity than conventional herbicides, using 3-(substituted phenyl)-! As a result of further research on -alkyl/, 3.41-oxazoline-coons, it was found that the phenyl group has a halogen atom at the 1-position and the da-position independently,
and that novel 3-(substituted phenyl)-1-alkyl-/, J, II-oxazoline-ones having a specific substituent at the 3-position have extremely excellent characteristics as herbicides. I found it.

[Means for solving problems]

The gist of the present invention is as follows: (wherein, Indicates the group that can be used.

Among the above substituents, R''#: represents a t* elementary atom or an alkyl group, and A represents a group represented by -OR'tfc represents -N;

In the above substituents, R4 represents an alkyl group, R1 and R
1 represents the same or different hydrogen atom or alkyl group. ) 3-(substituted phenyl)-s-alkyl-'
l'+daroxazoline-coons and herbicides containing these as active ingredients.

Next, the present invention will be specifically explained.

The 3-(substituted phenylcouteralkyl-/, 3.e-oxazoline-coon) incorporated as a herbicide in the present invention is represented by the above general formula (1).

In the general formula (I), X and Y each independently represent a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom, and preferably a fluorine atom or a Fichlorine atom. R' represents an alkyl group having -4 carbon atoms, preferably a straight-chain or branched alkyl group having 3 to 2 carbon atoms. O is an alkyl group with carbon number / -, -4, preferably an alkyl group with 1 to 2 carbon atoms; an alkenyl group with 7 to 6 carbon atoms, preferably an alkenyl group with 3 to 3 carbon atoms: an alkynyl group with 3 to 3 carbon atoms Preferably a glopargyl group; an alkoxyalkyl group having a total number of carbon atoms of -10; preferably an alkoxyalkyl group having FiR elements m1Z3 to S; Mata11-! −↓Indicates a group represented by A.

In the above substituents, R1 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, preferably an alkyl group having 1 to 6 carbon atoms,
A represents a group represented by →K or -N<:.

Among the above substituents, R4d carbon number/, A preferably an alkyl group having 7 carbon atoms, R1 and R@ are the same or different, and a hydrogen atom or an alkyl group having 1 carbon atoms, preferably 7 carbon atoms. Indicates several to six alkyl groups.

The compound of the present invention represented by the general formula (1) can be produced, for example, by reacting a hydrazide derivative represented by the general formula (Kawa) with phosgene or trichloromethyl chlorocarbonate.

(In the above reaction formula, %X, Y, R' and pt have the same meanings as above.) This reaction can be carried out without solvent or in benzene or toluene.

Aromatic hydrocarbons such as xylene, halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride,
Ethers such as diethyl ether, tetrahydrofuran and dioxane, esters such as ethyl acetate and butyl acetate, in solvents such as water, triethylamine, pyridine,
N.

N-dimethylaniline, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate.

Hydrogen carbonate) is carried out at -30,140°C in the presence or absence of a base such as IJium and/or a phase transfer catalyst such as benzyltrimethylammonium chloride, n-butylammonium bromide.

The hydrazide derivative (1), which is a raw material compound, can be synthesized, for example, according to the following route.

(In the above reaction formula, X, Y, R1 and R'' have the same meanings as above, Rv represents a lower alkyl group, Zl represents a halogen atom such as a chlorine atom or a bromine atom, and 2' represents a chlorine atom or a bromine atom. atom, a halogen atom such as an iodine atom, or a sulfonate group such as methanesulfonate or p-toluenesulfonate.t) The thus obtained compound of the present invention can be used as a herbicide as it is, but it is usually carried in an inert liquid carrier or solid. Mix it with a carrier and add an appropriate surfactant to it to form an emulsion, powder, or granule.

It is used in the form of tablets, irrigators, etc.

Liquid carriers include toluene, -silene, methylnaphthalene, cyclohexane, butanol, glycol, dimethylsulfonamide, dimethylformamide, acetone, methyl isobutyl keto/, animal and vegetable oils, fatty acids, fatty acid esters, water, etc. As a carrier, clay,
Examples include kaolin clay, talc, tonite, diatomaceous earth, silica, calcium carbonate, and vegetable powders such as soybean flour and wheat flour. Furthermore, if necessary, it can be used in combination with other active ingredients such as agricultural fungicides, insecticides, nematicides or other herbicides, plant growth regulators, soil conditioners and fertilizers. Further, in order to obtain a reliable herbicidal effect, auxiliary agents such as a spreading agent, an emulsifier, a wetting agent, and a fixing agent may be appropriately mixed.

The application amount of the herbicide of the present invention varies depending on the type of compound used, the target weed, the treatment time, the treatment method, the nature of the soil, etc., but usually the active ingredients are 7 ares and 90
, t ~ 10 grams.

Preferably, a range of o, r to jθ grams is appropriate.

〔effect〕

The compound of the present invention exhibits high herbicidal activity against many weeds in upland fields and paddy fields, while in single-crop crops such as whiteweed, pigweed, Japanese knotweed, harpweed, Japanese commonweed, purslane, leafminer, yellowtail, cyperus, hackberry, sycamore, cyperus, and paddy field, for example. , Azena,
Weeds such as weed grass, Japanese horseradish, Japanese chickweed, Japanese chickweed, Japanese grasshopper, Japanese cypress, Japanese cypress, and other weeds can be controlled in both the pre-emergence treatment and the growing season treatment. In addition, one compound of the present invention can be grown, for example, in rice, soybean, sunflower, cotton, potato, wheat, sugarcane,
It can be used as a selective herbicide in the cultivation of crops such as turmeric.

Furthermore, the compound of the present invention can be used against weeds that have been difficult to control with existing herbicides, such as wild morning glory, Japanese crocodile, Japanese morning glory, wild mustard, Japanese grass, and johnson grass in paddy fields. For example, hotarui, mizugaya tsuri, and urikawa.

It has high herbicidal activity against black guinea pigs etc.

The compound of the present invention in this strain has the extremely excellent and surprising feature of having a very broad herbicidal spectrum and being highly safe for crops.

The scope of application of the compounds of the present invention is not limited to the above-mentioned types of plants, but can be used for other plants as well by the same application method.

〔Example〕

Next, the present invention will be explained in more detail with reference to Examples.
This issue does not go beyond the gist of the issue.

The present invention is not limited to the following examples.

Example 1-1-Butyl-3-[Darkrolow&-(:
/-(ethoxycarbonyl)furobyl f, t]-1-fluorophenyl]-/, j, U-oxazoline-one's original l-pivaloyruko [Dark Roro! −
C/-(ethoxycarbonyl)propylthio]---fluorofuchloro]hydrazine/, 17II was dissolved in toluene, cooled to 3°C in a water bath, added with sqg of trichloromethyl chlorocarbonate, and then stirred. A mixed solution of 21I and toluene (5d) was poured into triethylamine at the bottom.

After heating, the mixture was stirred at room temperature for one hour, washed with a saturated aqueous sodium bicarbonate solution, then with water, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent: ethyl acetate: hexane = /: 10) to obtain 14 g of the compound A listed in Table 1 (6%) as an oil. Obtained. The chemical spectrum of this compound was as shown below.

Compounds synthesized in the same manner and their physical properties are listed in Table 7.

Next, examples of formulations of the compounds of the present invention will be shown. In addition, "department" below,
"Excellent" means "parts by weight" and "parts by weight," respectively.

Formulation example/: Wettable powder table/Compound of the present invention Ag 19 parts, Carplex #1
0 (Shionogi Pharmaceutical Co., Ltd., trade name) λ□ part, N, N kaolin clay (Ueya Kaolin Co., Ltd., trade name) 33 parts, higher alcohol sulfate ester surfactant Nru! 5 parts of 09O (trade name, manufactured by Toho Kagaku Co., Ltd.) were blended and uniformly mixed and pulverized to obtain an irrigation agent containing 10% of the active ingredient.

Formulation Example SS part (manufactured by Koni Granules Co., Ltd.) and λ part of a succinate surfactant Eyarol OT-/(Toho Kagaku Co., Ltd., Haruna) were mixed and pulverized, and then 70 parts of water was added and stirred.Furthermore, This was extruded through holes with a diameter of 0 and 100 degrees Celsius using a kneading and granulating machine, dried at 200 degrees Celsius for one hour, and then cut into long pieces containing two or more active ingredients. Granules were obtained.

Formulation Example 3: 130 parts of the compound A of the present invention in Emulsion Table 1 is dissolved in a mixed solvent consisting of 30 parts of xylene and 3 parts of dimethylformamide, and 300 parts of the polyoxyethylene surfactant Tsuruzeichiru is added to this. X (Toho Chemical Co., Ltd., trade name)/j with some additions,
An emulsion containing 30% of the active ingredient was obtained.

Formulation Example 4t: Flowable agent Compound A of the present invention in Table 1, ? , 30 parts pre-mixed ethylene glycol 11 parts, soniball AO
JO3ko (Toho Chemical Co., Ltd., trade name)! part, xantham gum θ
, 7 parts, and 56.9 parts of water were well mixed and dispersed. Next, this slurry mixture was wet-ground using a sand grinder (Igarashi Kikai Co., Ltd.) to create a stable flowable agent containing 30% of the active ingredient. :Obtained.

〔Effect of the invention〕

Test Example 1 Flooded Soil Treatment Test A 7/100 are resin vat was filled with paddy alluvial clay loam, and after fertilization, an appropriate amount of water was added and plowed. Seeds of Japanese millet, Kikashigusa, and Firefly were mixed into the θ and jCm layers from the soil surface, and five expelled stems of Prunus japonicum and Cyperus japonica were transplanted to each bat.

On the other hand, rice seedlings at the 5-leaf stage (variety: Akinishiki, plant height:
/ 0-! ; CIIL b seedling quality: good) 3 per vat
One book was used as one plant, and each plant was stacked at an insertion depth of approximately 7 cIrL. Thereafter, the water depth was kept at about JJ, and granules containing the compound of the present invention as an active ingredient obtained in Formulation Example 38 after transplantation were obtained in the same manner as in Formulation Example 2. 3-(co,dardichloro-5-isogloboxyphenyl)-S-t-butyl-/, 3.41-oxazoline-kone (hereinafter abbreviated as comparative agent A) and S-(tI-chlorobenzyl) Granules containing -N,N-diethyl-thiol carbamate (hereinafter abbreviated as Comparative Agent B) as an active ingredient were dropped onto a predetermined lid flooded surface.

After the treatment, the plants were given a water reduction method of 3 cm/day for λ days, and then cultivated in a greenhouse, and the herbicidal effect and herbiological damage were investigated for 1 day after the chemical treatment.

The results are shown in Table 1. Furthermore, the evaluation of the herbicidal effect is was calculated and expressed as a herbicidal effect coefficient according to the following criteria.

In addition, the evaluation of drug damage is was calculated and expressed as a drug damage coefficient according to the following criteria.

Table - Ichikuri Comparative Agent A: Compound test example described in Tokuko Sho Dako No. 1791 Field soil treatment test Field field black was filled with soil in a 300-minute noir resin vat, and after fertilization, diced and corn were sown. Tea
~3cIrL was covered with soil.

Within this soil layer, weed grasshopper and foxtail grass.

After homogeneously mixing Bluetail, Whiteweed, and Polygonum, an aquarium containing the compound of the present invention as an active ingredient obtained according to Formulation Example 1, and comparative agents A and 3-(j, l-dichlorophenyl) -/, /-
An irrigation agent containing dimethyl urea (hereinafter abbreviated as Comparative Agent C) as an active ingredient was diluted with water, and an amount equivalent to 1011 fl/ml of spray liquid of 7 are was sprayed onto the soil surface under small power pressure. At the same time, we also investigated chemical damage to each crop.

The results are shown in Table 3. The herbicidal effect and phytotoxicity were evaluated in the same manner as in Test Example 1.

Table 3 ■ Test Example 3 Leaf Treatment Test G, filled with upland Kuroboku soil in a small polyethylene pot of Noir of trzo amount, and after fertilizing % of Golden Millet 2 Shiloza,
The Japanese knotweed was sown in each pot separately.

Cultivation management was continued in the greenhouse, and when the growth level of the test plants reached the leaf stage of the goldenrod Ita leaf stage and the first true leaf stage of the whitetail grass and Japanese knotweed, the compound of the present invention obtained according to Formulation Example 3 was added as an active ingredient. An emulsion obtained in the same manner as in Formulation Example 3, containing tadichloroglopionic acid anilide (hereinafter abbreviated as "comparative agent") as an active ingredient, was diluted with water, and then sprayed with water. An amount equivalent to 1 liter of liquid was sprayed using a small power pressurized sprayer. Thereafter, cultivation was managed in a greenhouse, and the weeding effect of natural pressure was investigated lj days after spraying the chemical.

The results are shown in Omotehiro. In addition, the herbicidal effect was evaluated using the same criteria as in Test Example.

table-da (Voluntary) Procedural Amendment Showa A77 February 25th 2. Name of the invention 3 Person making the amendment

Claims (2)

[Claims] (1) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (In the formula, X and Y each independently represent a halogen atom, R^1 represents an alkyl group, R^2 represents an alkyl group,
Indicates an alkenyl group, an alkynyl group, an alkoxyalkyl group, or a group represented by ▲ where there are mathematical formulas, chemical formulas, tables, etc. Among the above substituents, R^3 represents a hydrogen atom or an alkyl group, and A represents a group represented by -OR^4 or ▲which has a numerical formula, chemical formula, table, etc.▼. In the above substituents, R^4 represents an alkyl group, and R^5 and R^6 are the same or different and represent a hydrogen atom or an alkyl group. ) 3-(substituted phenyl)-5-alkyl-1
, 3,4-oxazolin-2-ones. (2) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (In the formula, X and Y each independently represent a halogen atom, R^1 represents an alkyl group, R^2 represents an alkyl group,
Indicates an alkenyl group, an alkynyl group, an alkoxyalkyl group, or a group represented by ▲ where there are mathematical formulas, chemical formulas, tables, etc. Among the above substituents, R^3 represents a hydrogen atom or an alkyl group, and A represents a group represented by -OR^4 or ▲which has a numerical formula, chemical formula, table, etc.▼. In the above substituents, R^4 represents an alkyl group, and R^5 and R^6 are the same or different and represent a hydrogen atom or an alkyl group. ) 3-(substituted phenyl)-5-alkyl-1
, 3,4-oxazolin-2-ones as active ingredients.