JPH1059808A - Herbicidal composition containing pyroglutamic acid or its salt - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a herbicidal composition having reduced chemical damage by using a quaternary ammonium salt herbicide and a pyroglutamic acid. SOLUTION: This herbicidal composition contains a quaternary ammonium salt herbicide and a pyroglutamic acid of the formula or its salt. The quaternary ammonium slat herbicide is preferably paraquat, diguat or the like. The compound of the formula occurs in an extract of Rehmannia glutinosa and is formulated to the herbicide in an amount of 0.01-10,000 pts.wt. per 1 pt.wt. of the herbicide. In a preferred embodiment, a saccharine such as sucrose is added to this composition in an amount of 0.01-10,000 pts.wt. The objective herbicidal composition well relieves phytotoxicity particularly to soy bends, cotton, beet, radish, potato, rape plant, tomato, peanuts and other broad leaf crop plants.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

[0001] The present invention relates to a novel herbicidal composition having reduced phytotoxicity to crops.

[0002]

2. Description of the Related Art Various compounds that reduce the phytotoxicity of herbicides associated with the cultivation of cultivated plants are referred to as safeners or antidotes. Examples of such a compound which does not affect the herbicidal action of the herbicide against harmful weeds or further enhances the herbicidal action and reduces the phytotoxicity to useful cultivated plants are disclosed in, for example, JP-A-6-145011. As described in JP-A-5-279204 and JP-A-6-287101, various proposals have been made so far.

[0003] However, many of the safeners disclosed so far remarkably reduce the herbicide's harmful effects on grasses such as rice, corn and wheat, but prevent broadleaf crops such as soybean, cotton and sugar beet. Since the phytotoxicity-reducing effect is insufficient and no phytotoxicity-reducing agent for these crops has been put to practical use yet, creation of a phytotoxicity-reducing agent in this field is demanded.

[0004] Pyroglutamic acid, one of the constituents of the present invention, is present in certain plants and is known to inhibit pollen germination and growth. or,
Pyroglutamic acid is known in the agricultural field as a nori culture improving agent (JP-A-60-6135), a herbicide activity enhancer (JP-A-59-181201) and the like. However, it is not known that pyroglutamic acid has a phytotoxic effect of herbicides.

[0005] It has also been reported that the extract of red pheasant can reduce the phytotoxicity of paraquat, RDA J. Agric. Sci. 36: 159-1.
65 (1994). However, in this document, what compounds in the extract have a phytotoxic effect,
That is, there is no mention of what the active body is.

[0006] Further, GB2290471A discloses that an extract of Rhododendron japonica reduces the phytotoxicity of paraquat and that the component having a phytotoxicity-reducing action is stachyose. As shown in the test examples described later, indeed, stachyose also has a phytotoxicity-reducing action of paraquat, but its phytotoxicity-reducing activity is very weak as compared with that of pyroglutamic acid or a salt thereof of the present invention. It is.

[0007]

SUMMARY OF THE INVENTION The present inventor has found that pyroglutamic acid contained in Acacia elegans extract is an active substance having an action of alleviating the phytotoxicity of paraquat by using various analytical techniques, and completed the present invention. did.

[0008]

DISCLOSURE OF THE INVENTION The present invention provides a quaternary ammonium salt herbicide and a compound of the formula

[0009]

Embedded image

A herbicidal composition containing pyroglutamic acid or a chemically acceptable salt thereof represented by the formula: quaternary ammonium salt-based herbicide, saccharide and formula

[0011]

Embedded image

A herbicidal composition characterized by containing pyroglutamic acid or a chemically acceptable salt thereof represented by the formula: and the use of pyroglutamic acid or a chemically acceptable salt thereof. This is a method for reducing the harm of herbicides.

The quaternary ammonium salt-based herbicide used in the present invention is not particularly limited as long as it is a herbicidal active ingredient having a quaternary ammonium salt structure. Preferably, paraquat, diquat, difenzoquat, morpham Coats, dietam coats and cyper coats, most preferably paraquats and diquats. Of course, the herbicidal compositions of the present invention can also use mixtures in any proportion thereof.

By adding a saccharide to the herbicidal composition of the present invention, the effect is more remarkably exhibited, and a stable phytotoxicity-reducing action is exhibited. Such saccharides include, for example, erythrose, erythrulose, arabinose, xylose, xylulose, ribose, ribulose, rhamnose, fucose, deoxyribose, deoxyglucose, glucose, fructose, mannose, galactose, sorbose, tagatose, sedoheptulose, Mannopeptulose, maltose, cellobiose, euonymibiose, gentiobiose, melibiose, primberose, bisianose, rutinose, raffinose, trehalose, sucrose, gentianose, scorodose, stachyose, velbascoose, most preferably sucrose. , Raffinose or stachyose.

Pyroglutamic acid can be used as such or as a chemically acceptable salt thereof. Of course, the use of mixtures thereof is also encompassed by the present invention. Its salt is preferred over free pyroglutamic acid.

The chemically acceptable salts of pyroglutamic acid include, for example, alkali metal salts such as lithium salt, sodium salt and potassium salt, for example, alkaline earth metal salts such as magnesium salt and calcium salt, and organic ammonium salts. And the like, preferably an alkali metal salt or an alkaline earth metal salt, and more preferably a sodium salt, a potassium salt, and a magnesium salt.

Pyroglutamic acid includes D-form and L-form optical isomers, and the present invention includes each simple substance and a mixture thereof at an arbitrary ratio, but preferably the L-form.

[0018]

BEST MODE FOR CARRYING OUT THE INVENTION The herbicidal composition of the present invention contains pyroglutamic acid and a salt thereof in an amount of 0.01 to 10,000 parts by weight, preferably 0.1 to 1 part by weight of a herbicide.
It can be blended in an amount of up to 1000 parts by weight. When a saccharide is contained, the saccharide can be added in an amount of 0.01 to 10000 parts by weight, preferably 0.1 to 1000 parts by weight.

The herbicidal composition of the present invention is mainly applied to plants by foliage.
Mixing with a carrier and, if necessary, other adjuvants, a formulation usually used as a herbicide, for example, powder, coarse powder, fine granule, granule, wettable powder, emulsion, liquid, aqueous suspension, It may be prepared into a water dispersible granule, an oil suspension or the like and sprayed.

As a method for reducing the phytotoxicity, the above-mentioned composition can be treated simultaneously with a premix or a tank mix. Sequential treatment is also possible, in which plants are treated with a salt, pyroglutamic acid or a combination of a salt thereof and a saccharide.

Suitable solid carriers used for preparing the herbicide of the present invention include clays represented by kaolinite group, montmorillonite group and attapulgite group, talc, mica, phyllite, pumice and vermiculite. Inorganic substances such as gypsum, calcium carbonate, dolomite, diatomaceous earth, magnesium lime, apatite, zeolite, silica, synthetic calcium silicate, soybean powder, tobacco powder, walnut powder, flour, wood powder, starch, Vegetable organic substances such as crystalline cellulose, coumarone resin, petroleum resin,
Synthetic or natural polymer compounds such as alkyd resin, polyvinyl chloride, polyalkylene glycol, ketone resin, ester gum, koval gum and dammar gum; waxes such as carnauba wax and beeswax; and urea.

Suitable liquid carriers include paraffinic or naphthenic hydrocarbons such as kerosene, mineral oil, spindle oil and white oil; aromatic hydrocarbons such as benzene, toluene, xylene, ethylbenzene, cumene and methylnaphthalene; Chlorinated hydrocarbons such as carbon chloride, chloroform, trichloroethylene, monochlorobenzene, O-chlorotoluene, dioxane, ethers such as tetrahydrofuran, acetone, methyl ethyl ketone,
Ketones such as diisobutyl ketone, cyclohexanone, acetophenone and isophorone, esters such as ethyl acetate, amyl acetate, ethylene glycol acetate, diethylene glycol acetate, dibutyl maleate and diethyl succinate, methanol, n-hexanol, ethylene glycol and diethine glycol , Cyclohexanol, alcohols such as benzyl alcohol, ethylene glycol ethyl ether, ethylene glycol phenyl ether, diethylene glycol ethyl ether,
Examples thereof include ether alcohols such as diethylene glycol butyl ether, polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.

Surfactants used for the purpose of emulsification, dispersion, wetting, spreading, integration, control of disintegration, stabilization of active ingredients, improvement of fluidity, rust prevention, etc. are nonionic, anionic and cationic. Both ionic and zwitterionic ones can be used, but usually non-ionic and / or anionic ones are used. Suitable nonionic surfactants include:
For example, lauryl alcohol, stearyl alcohol, higher alcohols such as oleyl alcohol polymerized with ethylene oxide, isooctylphenol, nonylphenol and the like, and ethylene oxide polymerized with ethylene oxide, butyl naphthol,
Monoalkyl esters of alkyl naphthol such as octyl naphthol with ethylene oxide, ethylene oxide with higher fatty acids such as palmitic acid, stearic acid, and oleic acid, monoesters of these nonionic surfactants and phosphoric acid , A mixture of diesters, triesters or sulfates and their salts, dodecylamine, stearic acid amide and other amines polymerized with ethylene oxide, higher fatty acid esters of polyhydric alcohols such as sorbitan and polymerized ethylene oxide. And those obtained by polymerizing ethylene oxide and propylene oxide. Suitable anionic surfactants include, for example, sodium lauryl sulfate, alkyl sulfates such as oleyl alcohol sulfate amine, sodium dioctyl sulfosuccinate, sodium isopropylnaphthalenesulfonate, sodium methylenebisnaphthalenesulfonate, And aryl sulfonates such as sodium lignin sulfonate and sodium dodecylbenzene sulfonate.

Further, the herbicide of the present invention contains casein, gelatin, and the like for the purpose of improving the properties of the preparation and enhancing the biological effect.
Polymeric compounds such as albumin, glue, sodium alginate, carboxymethylcellulose, methylcellulose, hydroxyethylcellulose, polyvinyl alcohol and the like, and other auxiliaries can also be used in combination.

Polymeric substances such as above and other auxiliaries can be used in combination.

The above-mentioned carriers and various auxiliaries are appropriately used alone or in combination depending on the purpose in consideration of the dosage form of the preparation, the application scene, and the like.

The powder usually contains, for example, 1 to 25 parts by weight of the active ingredient compound, and the remainder is a solid carrier.

As the wettable powder, for example, the compound of the active ingredient is usually added in 2 parts.
The content is 5 to 90 parts by weight, and the balance is a solid carrier and a dispersing wetting agent. If necessary, a protective colloid agent, a thixotropic agent, an antifoaming agent and the like are added.

The granules usually contain, for example, 1 to 35 parts by weight of the active ingredient compound, and the remainder is mostly a solid carrier. The active ingredient compound is uniformly mixed with the solid carrier, or is uniformly fixed or adsorbed on the surface of the solid carrier, and the rule of the grain is about 0.2 to 1.5 mm.

The emulsion usually contains, for example, 5 to 30 parts by weight of an active ingredient compound, which contains about 5 to 20 parts by weight of an emulsifier, and the remainder is a liquid carrier. Is added.

The herbicidal composition applied in various dosage forms has a herbicide application rate of 0.3 to 10 per hectare.
kg, preferably 0.5 to 4 kg per hectare, and pyroglutamic acid or a salt thereof is 1 kg.
It is used in an amount of 0.1 to 100 kg per hectare, preferably 0.5 to 50 kg per hectare. Sugars are 0.1-30%, preferably 1-20%
A spray solution having a concentration of

[0032]

EXAMPLES Hereinafter, the herbicidal composition of the present invention will be described more specifically, but the present invention is not limited to the following. Note that “parts by weight” indicates% by weight.

[0033]

Example 1 (Wettable powder) 15 parts by weight of pyroglutamic acid, 1.5 parts by weight of paraquat, 72.5 parts by weight of clay, 3 parts by weight of white carbon, 5 parts by weight of sodium ligninsulfonate, and alkyl 3 parts by weight of sodium naphthalene sulfonate were mixed and pulverized to obtain a uniform wettable powder.

[0034]

Example 2 (Granules) 15 parts by weight of pyroglutamic acid, 1.5 parts by weight of paraquat, 30 parts by weight of bentonite, 2 parts by weight of sodium dodecylbenzenesulfonate, and 3 parts by weight of sodium ligninsulfonate were mixed. And 48.5 parts by weight of water, kneaded with a kneader, granulated with a granulator, and then dried to obtain granules.

[0035]

Example 3 (Solution) Pyroglutamic acid 15 parts by weight, paraquat 1.
5 parts by weight and 83.5 parts by weight of water were mixed to obtain a liquid preparation.

[0036]

Example 4 (Solution) Pyroglutamic acid 15 parts by weight, paraquat 1.
5 parts by weight, 15 parts by weight of stachyose, and 68.5 parts by weight of water were mixed to obtain a liquid preparation.

[0037]

Test Example The herbicidal composition of the present invention was tested for its effect on reducing crop phytotoxicity by the following method.

[0038]

[Test Example 1] Soybean seeds and sugar beet seeds were sown in a plastic pot containing cultivated soil, and 1 seeded in a greenhouse.
After four days of cultivation, the seedlings were mixed with a sodium salt of L-pyroglutamic acid and paraquat prepared according to Example 3 and sprayed. The concentration of the sodium salt of L-pyroglutamate in the spray liquid was 0.4 to 1.6%, and the concentration of paraquat was 25 ppm or 50 ppm, and the spray was applied so that the plants were sufficiently wetted. After spraying, place in greenhouse 29
After a time, the state of the phytotoxicity was observed and determined. Tables 1 and 2 show the results.
Shown in The degree of phytotoxicity was from 0 to 10 levels, where 0 was no phytotoxicity (complete phytotoxicity reducing activity) and 10 was no phytotoxicity (complete killing) (the same applies to the following test examples).

[0039]

[Table 1] ──────────────────────────────────── Active ingredient phytotoxicity (soybean) ── ２５ 25 ppm paraquat 7 0.4% L-pyroglutamic acid Na salt + 25 ppm paraquat 2 0.8% L-pyroglutamic acid Na salt + 25 ppm paraquat 2 1.6% L-pyroglutamic acid Na salt + 25 ppm paraquat 0 50 ppm paraquat 10 0.4% L-pyroglutamic acid Na salt + 50 ppm paraquat 6 0.8% L-pyroglutamic acid Na salt + 50 ppm paraquat 6 1.6% L-pyroglutamic acid Na salt + 50 ppm paraquat 1──────────────────────────────── ────

[0040]

[Table 2] ──────────────────────────────────── Active ingredient phytotoxicity (sugar beet) ─ ５０ 50 ppm paraquat 10 0.4% L-pyroglutamic acid Na salt + 50 ppm paraquat 4 0.8% L-pyroglutamic acid Na salt + 50 ppm paraquat 1 1.6% L-pyroglutamic acid Na salt + 50 ppm paraquat 2─────────────────────── ─────────────

[0041]

Test Example 2 Soybean seeds were sown in a plastic pot containing cultivated soil, cultivated in a greenhouse for 11 days, and L-pyroglutamic acid and its sodium salt prepared according to Examples 3 and 4 were used for the seedlings. Potassium and magnesium salts, sugars and paraquat were tank mixed and sprayed. The concentration of L-pyroglutamic acid and its salt in the spray liquid was 0.8%, the sugar was 67.7 mM, and the concentration of paraquat was 5%.
0 ppm (Tables 3 and 4) or 100 ppm (Table 5)
The plants were sprayed so that they were sufficiently wet. After spraying, it was placed in a greenhouse, and 24 hours later, the state of chemical damage was observed and determined. Table 3 shows the results
To 5 are shown.

[0042]

[Table 3] 程度 Active ingredient phytotoxicity (soybean) ── ────────────────────────────────── 50 ppm paraquat 9 0.8% L-pyroglutamic acid Na salt + 50 ppm paraquat 3 0.8% L-pyroglutamic acid K salt + 50 ppm paraquat 2 0.8% L-pyroglutamic acid Mg salt + 50 ppm paraquat 4 ────────────

[0043]

[Table 4] ──────────────────────────────────── Active ingredient phytotoxicity (soybean) ── ────────────────────────────────── 50 ppm paraquat 10 67.7 mM stachyose + 50 ppm paraquat 5 67.7 mM sucrose + 50 ppm paraquat 6 67.7 mM raffinose + 50 ppm paraquat 7 0.8% L-pyroglutamic acid Na salt + 50 ppm paraquat 3 0.8% L-pyroglutamic acid Na salt + 67.7 mM stachyose + 50 ppm paraquat 0 0.8% L-pyroglutamic acid Na salt + 67.7 mM sucrose + 50 ppm paraquat 20.8% L-pyroglutamic acid Na salt + 67.7 mM raffinose + 50 ppm paraquat 1１

[0044]

[Table 5] ──────────────────────────────────── Active ingredient phytotoxicity (soybean) ── ────────────────────────────────── 50 ppm paraquat 9 67.7 mM stachyose + 50 ppm paraquat 8 100 ppm L-pyroglutamic acid sodium salt + 67 .7 mM stachyose + 50 ppm paraquat 1 100 ppm L-pyroglutamic acid K salt + 67.7 mM stachyose + 50 ppm paraquat 1 100 ppmL-pyroglutamic acid Mg salt + 67.7 mM stachyose + 50 ppm paraquat 2──────────────────結果 The results in each of the above tables indicate that L-pyroglutamic acid or a salt thereof, and in some cases, a compounding agent with sugar, soybean and sugar against paraquat. It shows that beet phytotoxicity is significantly reduced.

[0045]

EFFECTS OF THE INVENTION The herbicidal composition of the present invention has excellent herbicidal effects and has very little phytotoxicity to crops, especially broadleaf crops, and can be used for a wide range of crops.

The herbicidal composition of the present invention can be used for crops in general, and particularly, for soybean, cotton, sugar beet,
It has good phytotoxic effect on a wide range of broadleaf crops such as radish, potato, rape, tomato, and peanut.

Most of the conventional safeners are safeners for gramineous crops such as corn, rice and wheat. The safeners for broadleaf crops such as the present invention are extremely rare and useful. is there.

──────────────────────────────────────────────────の Continued on the front page (51) Int.Cl. ⁶ Identification code Agency reference number FI Technical display location A01N 43:90) (72) Inventor Yoshihiro Okamoto 1041 Yasu-cho, Yasu-cho, Yasu-gun, Shiga Prefecture Sankyo Stock Company ( 72) Inventor Li Hisol Seoul-Sigannam-Gu-de-chi-Dong 316 Umma Apt. 16−603

Claims (10)

[Claims] 1. A quaternary ammonium salt herbicide and a compound represented by the formula: A herbicidal composition comprising pyroglutamic acid represented by the formula: or a chemically acceptable salt thereof. 2. The herbicidal composition according to claim 1, wherein the quaternary ammonium salt herbicide is paraquat. 3. The herbicidal composition according to claim 1, wherein the quaternary ammonium salt herbicide is diquat. 4. A quaternary ammonium salt herbicide, a saccharide and a compound represented by the formula: A herbicidal composition comprising pyroglutamic acid represented by the formula: or a chemically acceptable salt thereof. 5. The herbicidal composition according to claim 4, wherein the quaternary ammonium salt herbicide is paraquat. 6. The herbicidal composition according to claim 4, wherein the quaternary ammonium salt herbicide is diquat. 7. The herbicidal composition according to claim 4, wherein the saccharide is sucrose. 8. The herbicidal composition according to claim 4, wherein the saccharide is raffinose. 9. The herbicidal composition according to claim 4, wherein the saccharide is stachyose. 10. A method for reducing the phytotoxicity of a quaternary ammonium salt-based herbicide, comprising using pyroglutamic acid or a chemically acceptable salt thereof.