JPS61200901A - Herbicide - Google Patents

Abstract

PURPOSE:To provide a novel herbicide containing excelsin, etc., extracted from vegetables as organic components, exhibiting excellent herbicidal effect to various weeds and free from phytotoxicity to important crops such as corn, wheat, rice, soybean, cotton, etc. CONSTITUTION:The objective herbicide contains, as active component, excelsin of formula I separated from Ailanthus excelsa (a plant of Simaroubaceae family) and reported to have carcinostatic activity, or the compound of formula II [ailanthinone (R is group of formula III) or glaucarubinone (R is group of formula IV)], or an extract containing excelsin, ailanthinone or glaucarubinone extracted from a plant. The extraction of the above active component is carried out by conventional process for the extraction of natural component, e.g. by the extraction with an organic solvent such as methanol, acetone, ethyl acetate, etc., followed by concentration, etc. The herbicide is effective against broad- leaved weeds such as white-bird's-eye, green amaranth, etc., gramineous weeds such as barnyard grass, green foxtail, etc., commelinaceous weeds such as dayflower, etc.

Description

DETAILED DESCRIPTION OF THE INVENTION A novel product characterized in that the active ingredient is an extract of a plant containing stamin, exercinone, illancinone, glaucarbinone, or exercinone, illancinone, or glaucarbinone. Conventionally, typical natural organic compounds with herbicidal activity include antibiotics produced by actinomycetes and other microorganisms; ) K-related pheno-/I/-based compounds, acetylene-based compounds, flavone-based compounds, and norditerpenoid lactones are known. As a result of our search for plant components that have herbicidal activity against weeds, the present inventors found that: Quassinoids extracted from plants, such as exercin, ilansinone, and glauca μ.
We have obtained the new knowledge that extracts containing binone or m-reed exercin, ailansinonke young L< or glauca, and binone exhibit significant herbicidal effects against various weeds, and have developed the novelty of the present invention. This led to the completion of a herbicide.

Excellain, that is, the formula (I
) was isolated by H et al., but by S, Khan et al. F) India
n J, C.

19B 184 (1980) Alla of the Bitteraceae plant
Ailanthinone, which has been reported to be isolated from nthusexe@1mm.
) and glaucarubi
non@), that is, the compound represented by the formula (6), are all A11anthns exe
Isolated from @lsm, S. M. Kupehan
et al., J. Org, Ch@n, 40(5)
654 (1975) KPierreod@ndro
It has also been reported that the same compound was isolated from A11 anthnssxc@1sm in Lloydia 40(6) 579 (1977) by K Ogura et al.

Regarding the physiological activities of these quasinotide compounds, there are reports of anticancer effects (K Ogura @tml, ).

Lloydim, 40(6) 579 (1977))
However, the herbicidal effect on weeds is 1. The active ingredients of the herbicide of the present invention have not been reported so far. It is a carbinone-containing extract, and its extraction method includes the usual extraction methods for natural products, such as methanol, ethanol, acetone, ethyl acetate, ether, methylene chloride, chloroform, n-hexane, toluene, Methods such as extraction and concentration using an organic solvent such as benzene can be applied. The herbicide of the present invention, namely Exe~V:/or the extract containing ExeA/V of plants can be obtained by -example. 〇Reference Example 1 [70-ethanol aqueous extract (hereinafter referred to as extract A)] Plerreodendron that was collected and naturally dried
150 tons of crushed leaves and stems of J6rstingii were crushed using a mixer, and 500 tons of 70-ethanol aqueous solution was added.
The extract obtained by immersion in mJ and O filtration, which was left overnight at room temperature, was concentrated under reduced pressure to obtain a brown viscous liquid extract (extract A).
10.9ft-obtained 90 Reference Example 2 [Chloroform extract (hereinafter referred to as extract B◇)] After dissolving the extract AI0.6F obtained in Reference Example 1 in chloroform and removing insoluble matter by filtration. The chloroform-soluble portion was concentrated under reduced pressure to obtain 1.4F of a brown viscous liquid (extract B).

Reference Example 8 (Isolation of Exelsin) 120 mF of the extract B obtained in Reference Example 2 was dissolved in a small amount of chloroform, and a thin silica gel plate (thickness: 0.6 wm,
2Qx2Qa*, Msrek Ki@se1g@
16G F254) Placed on 8 plates, developed with a 9:1 mixture of chloroform and methanol, scraped off the region with Rf = 0.45, eluted with ethyl acetate, and distilled off under reduced pressure to obtain colorless crystals. /L/! /ton 22mt was obtained.

Melting point: 268-270°C [Literature value: Indlan
J, C, 19B184 (1980), melting point 1263-2
[64°C] In addition, the herbicide of the present invention, i.e., ailanthinone, glauca-vinone, or extracts containing ailanthinone or glaucabinone from plants, can be used to control the herbicides, such as the leaves and stems of Ailamthnm. υ Can be obtained by the following extraction step @ Reference Example 4 [70 thietano ~ aqueous extract (hereinafter referred to as extract C)] A11 anthns *xe@l which was collected and naturally dried
A. am leaves and stems were ground in a mixer. Crushed material 185
F was immersed in an aqueous solution of 70 mjK at 500 mjK and left overnight at room temperature. The extract obtained by filtration was concentrated under reduced pressure to obtain a brown viscous liquid extract (extract C) of 4.62%. Reference Example 5 [Chloroform extract (hereinafter referred to as extract 0)] The extract C8,7F obtained in Reference Example 4 was dissolved in chloroform, the insoluble matter was removed by filtration, and then the chloroform-soluble part was vacuumed. It was concentrated to obtain a brown viscous liquid (Extract D) 0.8F.

111 Example 6 (Isolation of Ilanshinone and Gutsuuka p-vinone) Extract D 406■e obtained in Reference Example 5 was dissolved in a small amount of chloroform, and a silica gel layer plate (thickness 0.5■e
20x20cm, Ki*se1g* 6 manufactured by Merek
G F254) 10 & 8 of toluene = acetone
:Developed with a mixture of 2, Rf=0.48 and Rf-0
, 27 was scraped off, eluted with ethyl acetate, and evaporated under reduced pressure to produce colorless plate-like crystals of ylanshinone 8.
5 mW from the latter site to the colorless platelet glauca p
4.5 mf of vinylone was obtained. Melting point of ylanshinone = 286-288℃ [Literature value: J
, Org, Ch@w,, 40(5) 654(1
975) = Melting point; 227-280°C] Melting point of glaucarbinone: 228-226°C [Literature value:
Phytoeh@m1try 4149 (1965)
-Melting point! 221h280℃] The herbicide of the present invention can be used to treat various weeds that are problematic in foliage treatment and soil dust treatment in fields.
For example, sopkazufu, snailweed, purslane, chickweed, whiteweed, blueberry, Japanese radish, Japanese radish, shepherd's purse, Japanese radish, golden deer, field pansies, ginseng, yellow violet, morning glory, morning glory, European bindweed, Japanese snail, hotokenoza, Broad-leaved weeds such as Japanese morning glory, Japanese dogwood, Japanese flowering plant, Japanese flowering plant, Japanese dogwood, corn marigold, grass family weeds such as Japanese barnyard grass, Japanese barnyard grass, foxtail grass, silver grass, and sycamore, and dayflower weeds such as dayflower,
The herbicide of the present invention has a herbicidal effect against weeds of the Cyperaceae family such as Cyperaceae, and does not cause any immediate damage to major crops such as corn, wheat, rice, soybean, and cotton.

In addition, the herbicide of the present invention can be used to kill various weeds that become a problem during the flooding of rice fields, such as grass weeds such as Japanese millet, broad-leaved weeds such as azalea, azalea, and chickweed;
It has a herbicidal effect on grasshoppers, etc., and does not cause any harmful effects on rice.

The herbicide of the present invention is usually mixed with solid carriers, liquid carriers, surfactants, and other formulation auxiliaries to formulate emulsions, aqueous preparations, suspensions, granules, aqueous solutions, etc. contains Exevn, Ilanshinone or Guouka μbinone as an active ingredient, in a weight ratio of 1 to 80%.
-1 Preferably 6 to 60- Containing 〇Solid carriers include kaolin clay, attapageite clay, bentonite, acid clay, pyrophyllite, limestone, diatomaceous earth, calcite, lime powder, urea, ammonium sulfate, Examples include fine powders or granules such as synthetic hydrous silicon oxide, and liquid carriers such as aromatic hydrocarbons such as xylene and methylnaphthalene, isopropano! , alcohols such as ethylene glyco-μ and cellosolve, ketones such as acetone, cyclohexanone and isophorone, vegetable oils such as soybean oil and cottonseed oil, dimethyspoxyte, acetonitrile, water and the like.

Surfactants used for emulsification, dispersion, wet charcoal, etc. include alkyl sulfate ester A/salt, alky
) Sulfonic acid salts, anionic surfactants such as sulfonic acid salts, shea μ kisshosohaku 11m, polyoxyethylene 7-kylari-di-te phosphoric acid NTE μ salts, polyoxyethylene aμ
Examples include non-ionic surfactants such as Ki μ ether μ, polyoxyethylene aryl ether, polyoxyethylene polyoxypropylene block copolymer, sorbitan fatty acid ester μ, and polyoxyethylene sorbitan fatty acid ester. ◎ Examples of auxiliary agents for formulations include Bugnin sulfonate, alginate, polyvinyl alcohol, gum arabic, CMC (boxymethymu cellulose), PAP (isopropylene acid phosphate), etc. @Next, a formulation example is shown.0 Note that parts indicate parts by weight.

Formulation Example 1 A wettable powder is obtained by thoroughly pulverizing and mixing Exe/&/V, 10 parts of ylancinone or Gufu carbinone, 8 parts of lignin sulfonic acid, 2 parts of sodium sulfuric acid, and 85 parts of synthetic hydrous silicon oxide. .

Formulation Example 2 50 parts of Extract B or Extract D, 8 parts of lignin μ calcium phosphate, 2 parts of Sodium Furi μ sulfate, and 45 parts of synthetic hydrous silicon oxide are thoroughly ground and mixed to obtain an irrigation agent. Formulation Example 8 Exe/L /Vn, 10 parts of ylancinone or glauca μbinone, 1v14 parts of polyoxyethylene styrene μphenylacetate, dode VIV benzenesulfonic acid strength/11
Mix well to obtain an emulsion Formulation Example 4 10 parts of Execin, ylancinone or glauca μvinone, 1 part of synthetic hydrous silicon oxide, 2 parts of ligninsulfonic acid lvVum, 25 parts of bentonite and 6 # parts of kaolin clay are thoroughly ground and mixed, water is added and the mixture is thoroughly kneaded, followed by granulation and drying to obtain granules.

Formulation Example 5 25 parts of Exercin, Ilanshinone or Guocarbinone, 8 parts of polyoxyethylene sopvitan monooleate
The herbicide of the present invention thus formulated can be applied to the soil before or after weed emergence. Treatment, foliage treatment, or waterlogging treatment.Soil destruction treatment includes soil surface treatment, soil mixing treatment, etc.For foliage treatment, in addition to treatment from above the plant body,
There are local treatments that treat only weeds so that they do not attach to crops.

In addition, when used in combination with other herbicides, it can be expected to increase herbicidal efficacy.In addition, it can be used as an insecticide, acaricide, nematicide, fungicide, plant growth regulator, fertilizer, and soil improvement agent. It can also be used in combination with other agents.

The herbicide of the present invention can be used in rice fields, fields, orchards, tea plantations, pastures, lawns, forests, non-agricultural lands, etc. When using extracts containing vinone, ilansinone, or glauca μbinone from plants as an active ingredient in herbicides, the amount of application should be determined based on weather conditions, formulation form, application timing, method, location, and target weeds. Although it varies depending on the target crop, etc., it is usually 1 arμ. 6tr~100
Emulsions, wettable powders, suspending agents, aqueous solvents, etc. are usually mixed in a predetermined amount at a rate of 91 liters A/~10 liters per 1 μm (if necessary, Spreading agents include the surfactants mentioned above, as well as the above-mentioned surfactants. Polyoxyethylene resin acid (ester), lignin sulfonate,
Examples include abietate, dinaphthylmethane disulfonate, paraffin, etc.Next, 0 herbicidal efficacy, which indicates a test example of the herbicide of the present invention, is a measure of the degree of budding and growth inhibition of test plants at the time of investigation with the naked eye. ROJ is defined as rOJ if there is no or almost no difference from the case when no test material is used, and "5" is defined as "5" when the test plant dies or its growth is completely inhibited.
It is evaluated on a scale of 0.06 and indicated as 0, 1.2.8.4.5.

Test Example 1 Upland Soil Mixing Treatment Test A cylindrical plastic bottle with a diameter of 10 cIR and a depth of 101 m) was filled with K upland soil, sown with chickweed, white locust, blueberry, and physalis, and covered with soil.

The test material was made into a hydrating powder according to Formulation Examples 1 and 2, a predetermined amount of it was diluted with water equivalent to 10 liters per area, and after being applied to the soil surface with a small sprayer, it was applied to a depth of 451 cm. The surface layer of the soil was thoroughly mixed.Furthermore, dice seeds were buried at a depth of 2m.After treatment, the plants were grown in a greenhouse for 20 days and their herbicidal efficacy was investigated.The results are shown in Table 1.

Chapter 1 Table Test Example 2 Field soil stem and leaf treatment test

Claims (1)

[Claims] A herbicide characterized by containing as an active ingredient exersin, ylanshinone, glaucarbinone, or an extract containing exersin, ylanshinone, or glaucarbinone from a plant.