JPS608278A - Oxadiazolinone derivative and herbicide - Google Patents

Abstract

NEW MATERIAL:The 1,3,4-oxadiazolin-5-one derivative of formula 1 (R1 is H or CH3; X and Y are Cl or CH3; R2 is alkyl, haloalkyl, alkoxy or phenyl). EXAMPLE:4-Acetyl-2-[1-(2,4-dichlorophenoxy)ethyl]-1,3,4-oxadiazolin-5- one. USE:Herbicide having strong herbicidal activity against a wide variety of weeds. PREPARATION:The compound of formula 1 can be produced by reacting the compound of formula 2 with the compound of formula 3 in a solvent such as benzene in the presence of a base such as triethylamine, pyridine, potassium carbonate, etc. at a temperature between 0 deg.C and the refluxing temperature of the solvent. A wide variety of weeds can be killed in about 2-3 weeks by applying 0.5-10kg of the compound of formula 1 per 1ha just before the sprouting of the weeds or at the initial growth stage thereof.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a 1,3,4-oxadiazolin-5-one conductor represented by the following general formula and a herbicide containing the compound as an active ingredient.

General formula (wherein R7 is R2 or CH,: X, Y is each ct or haC) I3: R2 represents haalkyl, haloalkyl, alkoxy, or phenyl. ) The 1,3,4-oxadiazolin-5-one derivative of the present invention represented by the above general formula is a new compound that has not been published in literature, patents, etc., and as a result of various studies conducted by synthesizing it, weed control has been achieved. In other words, the compound of the present invention has been found to have excellent herbicidal activity against a wide range of weeds, and the active ingredient can be applied immediately before the weeds germinate or at an early stage of their growth. 1 hectare per hectare from 05 to 10! If you apply 9, after about 2 to 3 weeks,
It can kill a wide range of weeds as described below.

In addition, by limiting the amount of this compound applied or by applying an appropriate application method, specific crops such as corn, potatoes, sugarcane, peanuts, soybeans, sunflowers, barley, wheat, turgid, paddy rice, cotton, and fruit trees can be treated. Weeds can be controlled in the field where they are cultivated.

Typical examples of the compounds of the present invention include those shown in Table F'51.

In addition, the compound is indicated by the symbol in the above general formula. Further, in the physical properties column, NMR indicates nuclear magnetic resonance spectrum, 0 indicates solvent mp, melting point, and η0 indicates refractive index, and the display method was according to a conventional method.

The compound of the present invention can be synthesized, for example, according to the following formula.

[2] The base used in this reaction is triethylamine.

Tertiary amines such as pyridine or alkalis such as potassium carbonate and sodium carbonate are used, and solvents include benzene, toluene, chloroform and dichloromethane.

An inert solvent such as dioxane, ethyl ether, dihydrofuran, acetone, methyl ethyl ketone, etc. or a tertiary amine itself used as a base may be used. The reaction temperature is θ
℃ ~ The reflux temperature of the melt is supplementary.

Typical synthesis examples are shown below and explained in more detail.

Synthesis Example 2- [1-(2,4-dichlorophenoxy)ethyl)
-1,3,4-oxadiazolin-5-one 2.0g
was dissolved in 5 ml of pyridine, and 1.5 rnl of acetic anhydride was added.
Add, shake well, and leave overnight. Benzene and water are added to the reaction solution, and the organic layer is separated and washed with water.

After drying with Glauber's salt, the solvent is distilled off under reduced pressure to obtain crystals. When this crystal is separated and thoroughly washed with cyclohexane, the target compound (s, r) is obtained at 2.2
10-2-methylphenoxy)methyl-1,3,4-
Oxadiazolin-5-one 2.4J to benzene 50m
/? and chloroacetyl chloride 1.51
Add. Cool the mixture in an ice-water bath and add 8 ml of triethylamine while stirring. After incubation, the mixture was allowed to react at room temperature for 30 minutes, and then heated under reflux for 3 hours. After returning the temperature to room temperature, insoluble materials are removed and subjected to florisil column chromatography to obtain crude crystals. This is recrystallized from a benzene-cyclohexane system to obtain the target compound (22) 2.1I.

-1,3,4-oxadiazolin-5-one 2-4l-
(4-chloro-2-methylphenoquine)ethyl] -1
, 25 g of 3,4-oxacyazolon-5-one was dissolved in 50 ml of benzene, and 16 I of ethyl chlorocarbonate was added.
1.5 g of triethylamine was added to the tube under water cooling. After use in the tube, heat and reflux for 2.5 hours. After cooling, add water,
Separate the organic layer and wash thoroughly with water. After drying with Glauber's salt, the solvent was distilled off under reduced pressure to obtain crude crystals. This was washed with cyclohexane to remove 2.8% of the target compound (A 17 ).
I get it.

The active compounds according to the invention can be prepared using customary formulation methods (+0: Ru.

Furthermore, the compounds of the present invention can be mixed with other herbicides. Furthermore, in order to expand the range of action, it can be used in combination with agricultural chemicals other than herbicides, such as insecticides and fungicides.

Next, examples of typical dosage forms will be given. "Department" in the description
indicates parts by weight.

Example 1. 50 parts of the compounds shown in Table 1 as active ingredients for irrigation agents, 10 parts of diatomaceous earth, 35 parts of clay, 83 parts of polyoxyethylene alkyl allyl ether sulfonic acid sorter and +2 parts of alkylnanthalene sulfonic acid sorter were mixed and ground. An aquarium containing 50% of the active ingredient compound is obtained.

When using, dilute with water to the specified concentration and spray.

Example 20 grains 5 parts of the compound shown in Table 1, 20 parts of bentonite, 73 parts of clay and 2 parts of sodium dodecylbenzenesulfonate were mixed,
After adding about 20 parts of water and kneading with a mixer, the mixture is granulated through a granulator, and then dried and sized to obtain granules containing 5 parts of the active ingredient.

Example 3. Emulsion 1 part of the compound shown in Table 1 as an active ingredient, 80 parts of kiln, and 5 parts of polyoxyethylene alkyl allyl ether are mixed to form a homogeneous solution, to obtain an emulsion containing 19 parts of the active ingredient. When using, dilute with water to the specified concentration and spray.

The novel 1,3,4-oxadiazolin-5-one derivatives of general formula I have excellent herbicidal activity and are therefore suitable for controlling weeds growing in fields, paddy fields, orchards, non-agricultural lands, etc. It is. When this active compound is sprayed on the soil surface or mixed into the soil, it can significantly inhibit the growth of weeds and cause them to die. Weeds can also be controlled by spraying a water solution on the stems and leaves of growing weeds.

The dosage of this compound is regulated to reduce the application amount to 0 per hectare.
．． If you select 5 to 5 k+7, corn, wheat, barley, rice, sugarcane 1. soybeans, peanuts,
It can be used as a selective herbicide in fields where sunflowers, potatoes, cotton, or fruit trees are grown. It can be applied as a non-selective herbicide by increasing the application rate.

The compounds of the present invention can be used, for example, to control the following weeds: That is, plants such as Stellaria media, C.
henopodium), Sagima j.
aponica), Chonopodiu
m ficifoliurn), Japanese knotweed (Po.
lygonum nodosum), purslane (Po
rtulaceoleracea), shepherd's purse (Caps
ella, bursapastoris) z Lepidium virginicum,
Cardamine Hexuosa (Porippa 1ndica), Cardamine Hexuosa % Abutilon avicennae, American Golden Deer (Sida 5pinosa), Ma/
l/Ipomoea purpurea
, Seneci.

vu! garis), Onifuke 8shi (Sonchus)
asper), Bidens
frondosa), Ambrosia a
rtemisiaefolia), Ast
er 5ubulatus), Ho+ganode (Lamiu
Oxalis (Oxa)
lis cornicolate), -) Aobiyu (A
maranthus retroflexus), Vicia 5ativa, Gali umspurjum, Solanum nigrum, Datura stramonium, Nagi adsendens), Ohishiba (Eleusine)
1ndica)) Setaria
viridis), Golden millet (Echinochlo)
r crus-galli), camo jig-length (Agro
pyrontsukushiensis), Hosomugi (
Lolium perenne).

Bromus catharticos, oat (Avenatatua), barnyard grass (Po)
lypogon H4gegaweri).

Panicum dichot om
if lorom) % Cyperus weeds, such as Cyperus croiria (Cype ru 5m1croiria)
, Cyperus 1ria, Eleocharis acicularia
etc.

The compound of the present invention has excellent herbicidal efficacy against a wide range of weeds as described above, and is particularly effective when sprayed on the field surface, the foliage surface of plants, or in waterlogged areas just before the weeds germinate or during the growing season. , an extremely high pest control effect can be obtained.

Also, when the compound of the present invention is mixed into soil, an extremely excellent weed control effect can be obtained.

In order to demonstrate the herbicidal effect of the herbicide according to the present invention, some representative test examples will be given and explained in more detail.

Test Example 1 Pre-emergence soil treatment (pre-emergence 5oi
Weeding effect on plants when using volcanic ash soil in pots with an area of 100 cm2, and
Golden millet (Echinochloa crus-gal)
li), Polygonum nodo
sum) % Amaranthus retr
offlexus), corn (Zeamays),
Seeds of wheat (Triticum aestivum) and japonica (Phaseolus radiotus) were sown and covered with about 50 ml of soil. was diluted with water and cast onto the soil surface of each pot in an amount equivalent to 9 parts of the active ingredient per hectare. After processing 2
The herbicidal effect on plants was investigated every week. The herbicidal effect was observed with the naked eye and is shown in Table 2 on a scale of 6 levels from 0: no effect to 5: complete death.

Test Example 2 Foliar 5play treat
ment) Herbicidal effect on plants when surface M 100cn? Fill a pot with volcanic ash soil and plant the
), Echinochloa crus-g
Polygonum n.
odosum), Amaranthus r.
etro-flexus), corn (Zeam
ays), wheat (Triticum aestivu)
m), Phaseolus radiotus
) seeds are sown, covered with about 1 cm of soil and placed in a greenhouse, and when the weeds have one or two leaves, an irrigation agent containing the compound of the present invention is applied at 1,000 doses equivalent to 10 kg per 1 hectare.
It was diluted with water equivalent to 1/ha and sprayed using a sprayer. Ten days after the chemical spraying, the test was conducted using the same criteria as in Test Example 1, and the results were expressed using a 6-level index. The test results are as shown in Table 3.

Test Example 3 Test for herbicidal effect on paddy weeds and phytotoxicity on paddy rice A pot with a surface area of 120 cm2 was filled with paddy soil,
Echinochoa crus-gallt),
:7 Nagi (Monochoria vaginalis)
) seeds were mixed into the soil approximately 2 cm above the surface, and the seeds of E.
leocharis acicularis) and two-leaf stage rice weeds were transplanted to two locations each, and the water depth was approximately 3 cm.
Keep it at m. Three days later, an aquarium containing the compound of the present invention prepared according to Example 1 was administered into the water in an amount equivalent to J 10 kg per hectare.

Three weeks after chemical treatment, the herbicidal effect and chemical damage to paddy rice were investigated. The herbicidal effect and the chemical damage to crops were determined by Test Example 1.
The survey was conducted using the same criteria as the above, and was expressed using a 6-level index. The test results are shown in Table 4.

Table 4 shows that the compounds of the present invention are effective in killing weeds, which are important weeds in paddy fields, such as Japanese grasshopper, Japanese grasshopper, and Japanese grasshopper.

Table-2 Pre-germination soil treatment Table-4 Waterlogging treatment procedure amendment (method) January/January 1980 Director-General of the Patent Office Kazuo Wakasugi 1, Indication of the case Patent Application No. 115943, 1982, 2, Title of the invention: Oxadiazolinone derivatives and herbicides 3. Relationship with the person making the amendment Patent applicant address: 13-8 Shiba Daimon-chome, Minato-ku, Tokyo Name (20
0) Showa Denko Co., Ltd. Representative Yasunobu Kishimoto 4, Agent (zip code 105) 5. Supplementary 11th day order stipulation September 2711, 1982 (shipment date) 6. Supplementary IF subject Ming + QIl No. 1 .2, 8.9, page 7 of each page, the i'th item of the detailed description as stated in the text of the amendment content type print,
Submission of each page of 2, 8.9

Claims (1)

[Claims] 1) General formula (wherein R4 is R9 or CH!: X, Y is each C2 or CH3: R2 is alkyl) -roalkyl. Indicates alkoxy or phenyl. ) A 1,3,4-oxadiazolin-5-one derivative represented by 2) General formula (wherein R1 is ■, or c■3: x and y are each CL or haC) I3: R2 represents alkyl, notsuroalkyl, alkoxy, or phenyl. ) A herbicide containing a 1,3,4-oxadiazolin-5-one derivative as an active ingredient as shown in the revised specification (no change in content).