JPH0372407A - Herbicide composition - Google Patents

Abstract

PURPOSE:To obtain the subject composition exhibiting excellent herbicidal effect at a low rate of application owing to synergistic effect, capable of completely exterminating weeds by single application and having high safety to paddy rice plant, etc., by compounding a specific compound with dymron and other compound and using the mixture as active component. CONSTITUTION:The active component of the objective composition is a mixture of (A) a compound of formula I {Q is group of formula II [R3 is (halogen- substituted) lower alkyl, halogen, group of formula III or formula IV (R4 is H, lower alkyl, halogen, lower alkoxy, etc.): R1 and R2 are lower alkyl or lower alkoxy] (e.g. the compound of formula V or formula VI) or its salt useful as a herbicide effective against annual and perennial weeds at a low rate of application, (B) 3,7-dichloro-8-quinolinecarboxylic acid of formula VII useful as a herbicide for cockspur-grass and (C) dymron [=1-(alpha,alpha-dimethylbenzyl)-3-(4- methylphenyl)urea] of formula VIII. The composition is useful in agricultural and horticultural field and exhibits excellent effect by the treatment of weeds before or after sprouting.

Description

[Detailed description of the invention] Industrial applications The present invention relates to a herbicide useful in the field of agriculture and horticulture.

Problems to be solved by conventional techniques and inventions Generally, in areas where herbicides are applied, many types of weeds grow together, and the germination and growth of each individual varies depending on the surrounding environmental conditions. , - not like that. In particular, in recent rice cultivation, the period for weeds to appear is becoming longer due to the earlier transplanting period. Therefore, herbicides are applied to many types of weeds at different growth stages, and in actual situations, it is difficult to kill all weeds with just one application. For this reason, the same or different herbicides are used repeatedly several times, but repeated use of such herbicides requires a great deal of labor and is undesirable, such as phytotoxicity of paddy rice and residue in the soil due to large amounts of application. It raises an issue.

Therefore, there is a strong desire for the emergence of a safe herbicide that has a wide herbicide spectrum, is effective against weeds that have advanced in growth even before they emerge, can maintain a suppressive effect for a predetermined period of time, and does not harm crops. .

The compound of general formula (I) below, which is the active ingredient of the present invention, has already been disclosed in Japanese Patent Application Publication No. 64-38091 by one of the inventors.
It is a compound disclosed as a herbicide in 2013, and it is highly effective against weeds and perennial weeds at an extremely low dose compared to conventional herbicides, and it is effective against rice seedlings under normal conditions of use in the field. It is an extremely safe herbicide for humans and livestock that does not cause problematic drug damage. However, there are cases in which the suppressive effect is insufficient in practical situations when the outbreak of novieum continues for a long period of time under natural conditions.

On the other hand, the conventionally known 3,7-dichloro-8-quinolinecarboxylic acid (hereinafter abbreviated as compound A) is a compound described in JP-A No. 57-165368, and is prepared under normal conditions.
Although it is a highly safe herbicide for rice when applied in a bag, it cannot be expected to have any practical effects on weeds other than weeds. Therefore, it has already been found that this problem can be solved by mixing compound A with general formula (I), but the mixture of general formula (1) and compound A is not safe for normal use on paddy rice seedlings. However, subsequent research has shown that under poor environmental conditions, such as shallow planting, poor posture, and especially when combined with high temperatures, can cause chemical damage to paddy rice. It was revealed.

The object of the present invention is to provide a herbicide for paddy rice that can reduce chemical damage even under such poor environmental conditions without impairing the high herbicidal effects of general formula (I) and compound A.

Means for Solving the Problems In order to solve the above problems, the present inventors set out to search for a herbicide that can completely control all weeds in one application and is highly safe for paddy rice. I have done extensive research. As a result, a compound represented by the following general formula (I) (hereinafter sometimes abbreviated as compound (1)), compound A and 1-Ca
, σ-dimethylbenzyl)-3-(4-methylphenyl)urine m (hereinafter referred to as compound B),
Solving these issues and obtaining an excellent herbicide;
That is, by mixing compound A with compound (I),
It also shows a practical sustained effect on weeds that occur over a long period of time under natural conditions, and by adding Compound B to these, it can be used without reducing its effectiveness against weeds.
It has been found that compound (1) reduces the phytotoxicity, and surprisingly also reduces the phytotoxicity of compound A, thereby suppressing the growth of virtually all weeds in rice fields with a single application. They also discovered that the inhibitory effect lasts so long that no weeding work is required before and after the weeding process, and that it exhibits excellent safety against paddy rice.Through further research, they completed the present invention.

That is, the present invention is based on the general formula (1) [wherein, Q is a lower alkyl group or a lower alkoxy group, and R3 is a lower alkyl group, a halogen atom, or a halogen-substituted lower The alkyl group, R4
represents a hydrogen atom, a lower alkyl group, a halogen atom, a lower alkoxy group, a lower alkylthio group, a lower alkylamino group or a di-lower alkylamino group. ] or a salt thereof; (2) 3,7-dichloro-8-quinolinecarboxylic acid (i.e., compound A) represented by the following formula; and (3) l-(α,σ -dimethylbenzyl)-3-(4
-Methylphenyl)urea (i.e., compound B, generic name Daimeron) as an active ingredient.

The herbicide composition of the present invention has excellent effects even when treated before or after the emergence of weeds, has no phytotoxicity to rice, and is useful as an excellent selective herbicide. In addition, it is not harmful to various crops other than rice, and is useful as an excellent selective herbicide. It can also be applied to control various weeds in agricultural and horticultural fields such as fields and orchards, and in non-agricultural lands. It has a great economic effect in weed control.

In the general formula (I), the lower alkyl group represented by Rt, Rs and R3 is preferably a linear or branched alkyl group having 1 to 4 carbon atoms, such as methyl, ethyl, propyl, isopropyl. .

Examples include butyl and inbutyl.

As the lower alkyl group represented by R6, in addition to the above-mentioned alkyl groups having 1 to 4 carbon atoms, pentyl, hexyl, etc. are also suitable, and linear or branched alkyl groups having 1 to 4 carbon atoms are preferable.

Examples of the halogen atom represented by R1 and R4 include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

The halogens of the optionally halogen-substituted lower alkyl group represented by R3 include those mentioned above.

The alkyl moiety in the lower alkoxy group represented by Rr, Rz, R4, and the alkyl moiety in the lower alkylthio group, lower alkylamino group, and di-lower alkylamino group represented by R4 also include the above, Rr, Rz
, and lower alkyl groups having 1 to 4 carbon atoms as described for Rs.

Examples of salts of the compound represented by formula (I) include salts with inorganic bases such as alkali metals (e.g., sodium, potassium, etc.), alkaline earth metals (e.g., calcium, etc.), ammonia, etc., and organic base salts. For example, dimethylamine, triethylamine,
Piperazine, pyrrolidine, piperidine, 2-phenylethylbenzylamine, benzylamine, ethanolamine.

Salts with jetanolamine etc. are used.

In addition, these compounds (I) are
It can be produced according to the method described in 91.

Representative examples of the compound represented by the general formula (I) are shown below. The following compounds are included in the compounds represented by the general formula (I), but the compounds represented by the general formula are not limited thereto.

For example, compound A can be produced by the method described in JP-A-57-165368. Compound B is commercially available as Shoron (generic name Daimeron).

Compositions according to the invention may vary depending on the relative activity of each component.
Generally, about 0.0 of compound (1) per part by weight of compound B
1-10 parts by weight, about 0.05-2 parts by weight of Compound A are suitable. The content ratio of compound (1) in the preparation is 0.05 to
Approximately 90% by weight is appropriate, but for granules it is approximately 0.0%.
5 to 10% by weight, preferably about 0.1 to 5% by weight are suitable. The content ratio of compound A in the preparation is approximately 0.05-9
0% by weight is suitable, but as granules, 0.1 to 5% by weight, preferably 0.5 to 2% by weight is suitable.

The content of Compound B in the formulation is suitably about 0.5 to 90% by weight, but as granules it is about 0.5 to 20% by weight.
, preferably about 1 to 10% by weight.

The appropriate amount of the herbicide composition to be applied varies depending on the application situation, application time, application method, target grass species, and crop quality.
Although it cannot be generally specified, the amount of active ingredient per area is generally about 0.
A suitable amount is 1 to 100 g, preferably about 1 to 50 g.

When applying the herbicidal composition of the present invention, the composition of the present invention may be dissolved or dispersed in a suitable liquid carrier, or mixed with a suitable solid carrier depending on the purpose of use. or adsorption, emulsion, irrigation agent 2
It is used in preparations such as granules, microgranules, microgranules F, and flowables.

These preparations may contain emulsifiers, spreading agents,
Penetrants, wetting agents, mucilage agents, stabilizers, etc. may be added, and they can be prepared by methods known per se. Liquid carriers (solvents) used include, for example, water, alcohols (e.g., methanol, ethanol, n-propanol, inpropanol, ethylene glycol, etc.), ketones (e.g.,
acetone, methyl ethyl ketone, etc.), ethers (e.g.
dioxane, tetrahydrofuran, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, 7'CF pyrene glycol heptamethyl ether, etc.), aliphatic hydrocarbons (e.g. kerosene).

kerosene, fuel oil 1 machine oil, etc.), aromatic hydrocarbons wX (e.g.
benzene, toluene, xylene, solvent naphtha, methylnaphthalene, etc.), halogenated hydrocarbons (e.g., dichloromethane, chloroform, carbon tetrachloride, etc.), acid amides (e.g., dimethylformamide).

Suitable solvents include dimethylacetamide, etc.), esters (e.g., ethyl acetate, butyl acetate, fatty acid glycerin ester, etc.), and nitriles (e.g., acetonitrile, propionitrile, etc.). Use a mixture of seeds or more in an appropriate ratio.

Solid carriers (diluents and bulking agents) include vegetable powders (e.g.
soybean flour, tobacco flour, wheat flour, wood flour, etc.), mineral powders (e.g. kaolin, bentonite, acid clay).

Clays such as clay, talcs such as talc powder, waxite powder,
Suitable materials include silicas such as diatomaceous earth and mica powder), alumina, sulfur powder, and activated carbon, and these may be used alone or in a mixture of two or more in an appropriate ratio.

As surfactants used as emulsifiers, spreaders, penetrating agents, dispersants, etc., soaps, polyoxyethylene alkylaryl ethers (e.g., Neugen, E.N. 142 (E, A142)) may be used as necessary. o Daiichi Kogyo Seiyaku (
(manufactured by Kao Corporation), polyoxyethylene aryl esters (e.g., nonal [F], manufactured by Toho Chemical Co., Ltd.), alkyl sulfates (e.g., Emar 10, Emar 40 [F], manufactured by Kao Corporation), alkyl Sulfonic acid salts (e.g., Neogen [F], Neogen To, Dai-Kogyo Seiyaku Co., Ltd.; Neoperex [F], Kao Corporation), polyethylene glycol ethers (e.g., [F], Danipol 85, Danipol 100o) , Noniphor 160 [F], manufactured by Sanyo Kaoru Co., Ltd., and polyhydric alcohol esters (L Tween 20o, Tween 80o, manufactured by Kao Corporation) and other nonionic and anionic surfactants are used.

In addition, the herbicide composition of the present invention may include insecticides, fungicides, fertilizers,
Pigments, fragrances, herbicides (e.g. S, S-dimethyl 2-(difluoromethyl)-4-(2-methylglobil)-6-(
Trifluoromethyl)-3,5-pyridine dilupotioate 1.) and the like may be blended as appropriate.

Effects of the Invention The herbicide composition for paddy rice with reduced phytotoxicity of the present invention is applicable to transplanted paddy rice and directly sown paddy rice, does not cause phytotoxicity to paddy rice in a wide range of processing periods, and can be used even under poor environments. It reduces chemical damage to a level that can be ignored in practical terms, and exhibits excellent herbicidal effects on annual weeds in paddy rice fields, such as Japanese grasshopper, Japanese cypress, Japanese cypress, Japanese azalea, and Kikashigusa.

EXAMPLE I The present invention will now be specifically explained with reference to formulation examples of the present invention, but the present invention is not limited thereto.

Formulation Example 1 Granule Compound No. 1 0.25% by weight
Compound A 1.0% by weight Compound 8 5.0% by weight Sodium ligninsulfonate 5.0% by weight Bentonite
15.0% by weight clay
A granule prepared by adding 12% by weight of water based on the total amount of the mixture to a 73.75% by weight mixture, kneading and granulating the mixture.

Formulation Example 2 Granules Compound No. 2 0.3% by weight Compound A 1.0% by weight Compound B
5.0% by weight Sodium ligninsulfonate 5.0% by weight Bentonite
15.0% by weight clay 7
3.7% by weight of the mixture, based on the total amount of this mixture
Granules made by adding % by weight of water and kneading and granulating.

Formulation Example 3 Wettable powder Compound No. 1 3.0% by weight Compound A Io, 0% by weight Compound 8
50.0% by weight Sodium lignin sulfonate 5.0% by weight Polyoxyethylene alkylphenyl ether (Noniball 85)
5.0% by weight clay 23.
White carbon 4.0% by weight
Irrigation agent made by mixing and pulverizing. (Use after appropriately diluting with water) Formulation example 4 Granule compound No. IO, 3% by weight
Compound A 1.0% by weight Compound 8 5.0% by weight Sodium ligninsulfonate 5.0% by weight Bentonite
15.0% by weight clay
A granule prepared by adding 12% by weight of water based on the total amount of the mixture to a 73.7% by weight mixture, kneading and granulating the mixture.

If the herbicide composition of the present invention is applied to the water surface from 5 days before transplanting paddy rice to about 15 days after transplanting paddy rice (from before the emergence of weeds to the peak growth period), or from the time of emergence to around the 4-leaf stage of directly sown paddy rice, Hand weeds and perennial weeds can be effectively controlled without causing chemical damage to paddy rice. At that time, the compound (I
), Compound A1 and Compound B can exhibit herbicidal effects on a wide range of weeds without reducing their respective activities as herbicides for paddy rice. In addition, it has a remarkable effect of reducing phytotoxicity on paddy rice even under adverse environmental conditions (high temperatures and poor planting posture), and it is possible to reduce phytotoxicity to a level that does not cause any practical problems, and the range of application can be reduced. It becomes possible to expand.

The usefulness of the present invention as a herbicide for paddy rice will be shown below in test examples.

Test Example 1 Test on the effect of reducing chemical damage under high temperature and poor environmental conditions of stacking (outdoor Wagner pot test) A 115,000 Earl Wagner pot was filled with paddy soil (sandy clay loam) and submerged in water to a depth of 5 cm after plowing. shall be. To this, two paddy rice seedlings (variety: Nipponbare) at the two-leaf stage (variety: Nipponbare) with three individuals per plant were placed in separate pots of 2 cm and -〇, 5.
The plants were transplanted to a depth of c+a (roots exposed to the soil surface for 0.5 am), and 2 days after transplantation, a predetermined amount of the granules prepared in Formulation Example 1 and Comparative Examples 1 and 2 was applied. The test was repeated three times. 21 days after the treatment, the plant height, number of stems, and above-ground drying chamber of the paddy rice were measured, and the ratio (%) to the untreated plot was calculated for each item using the following formula and displayed.

The average temperature during the test period was a maximum of 32.3°C and a minimum of 23°C.
．． The average temperature at 0°C was 26.5°C.

In addition, Comparative Example 1 was prepared by replacing Compound B1 or Compound No. 1 and Compound A with clay in the formulation of Formulation Example 1 above, and otherwise producing the formulation in exactly the same manner as in the same Formulation Example.
and 2.

The results are shown in Table 1.

Test Example 2 Test for the effect of reducing chemical damage under adverse environmental conditions of high temperature and water leakage (outdoor Wagner Bont test) A 115,000 Earl Wagner pot is filled with paddy soil (clay loam), and after watering and plowing, it is made into a 5 cm ice-making state. Two seedlings of paddy rice seedlings (variety: Nipponbare) at the two-leaf stage (variety: Nipponbare) were transplanted to a depth of 2CI11 with three individuals per plant, and 5 days after transplanting, Formulation Example 4, Comparative Examples 1, 2, 3, 4.5 and A predetermined amount of the granules prepared in step 6 was processed. After the treatment, water leakage of 2 cm per day was performed for 3 days. The test was repeated twice. 28 days after the treatment, the plant height, number of stems, and dry weight of the aboveground parts of the paddy rice were measured, and the ratio (%) to the untreated plot was calculated and displayed in the same manner as in Test Example 1.

The average temperature during the test period was a maximum of 33.3°C and a minimum of 21°C.
．． The temperature was 9°C, and the average temperature was 26.5°C.

In addition, in the formulation of Formulation Example 4, Compound B or Compound No. 1 and Compound A1 or Compound A1 or Compound No. 1 s or Compound A and Compound B1 or Compound No. 1 and Compound B were replaced with clay, and the others were replaced with clay. Comparative Examples 1, 2.3, 4.5, and 6 were prepared in exactly the same manner as the same formulation example.

The results are shown in Table 2.

Test Example 3 Weeding effect test in the field A paddy field made of sandy clay loam was plowed, flooded, and
After puddling, a test plot of 1 m4 in size was set up, and a certain amount of Japanese millet seeds, Japanese fireflies seeds, Japanese cabbage seeds, and other hand-grown weed seeds were sown thereto and the soil surface layer was mixed. Furthermore, 10 sprouted tubers of Urikawa, Mizugaya Tsuri, Kurogwai, and Omodaka were planted, and 24 plants of 2-leaf rice seedlings (variety: Nipponbare) were transplanted to a depth of 2 cm, with 3 individuals per plant.

5 days after transplanting (approx. 0.4 leaf stage) and 11 days after transplanting (approx. 0.4 leaf stage)
Formulation Example 4, Comparative Examples 1 and 2 (
A predetermined amount of each drug prepared according to the same method as described in Test Example 1 was applied to the water surface. The test was repeated twice, and the above-ground dry weight of each weed and rice plant was measured 60 days after treatment, the suppression rate (%) was calculated using the following formula, and the herbicidal effect and phytotoxicity were expressed as an index.

Judgment criteria for chemical damage OO~ 5 1 6-15 2 16-25 3 26-50 4 51-75 5 76-100 Judgment criteria for herbicidal effect and chemical damage index suppression rate (%) 0-5 6-25 26-50 51 ~75 76-90 1-100 An index of 5 in terms of herbicidal effect indicates a practically excellent effect, and an index of O in terms of drug damage indicates that it is extremely safe in terms of practical use.

The results are shown in Table 3.

Test Example 4 Applicability to flooded direct sowing cultivation of rice (field test) After plowing, flooding, and puddling a clay loam paddy field according to conventional cultivation, 1 section 2
．． A 5 m" test plot was set up, and a certain amount of Japanese millet seeds, Japanese fireflies seeds, and Konagi seeds were sown there, and the soil surface layer was mixed. Furthermore, paddy rice seeds (variety: Nipponbare) coated with Calper flour were sown at a depth of 1 cm. 8 days after sowing (rice 0.2
leaf stage, about 1.3 leaf stage of Japanese rice plant) and after 15 days (2.3 leaf stage of rice plant)
Four-leaf stage.

Formulation example 4. A predetermined amount of each drug formulated in Comparative Example 1 (same as described in Test Example 1) was applied to the water surface. The test was repeated three times, and after 38 days of treatment, the herbicidal effect on each weed and the chemical damage to rice were investigated in the same manner as in Test Example 3, and expressed using the same criteria.

The results are shown in Table 4.

(Margin below) Table 2

Claims (1)

[Claims] 1. (1) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, Q is ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ Numerical formulas, chemical formulas, etc.
There are tables, etc. ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. R_4 represents a hydrogen atom, a lower alkyl group, a halogen atom, a lower alkoxy group, a lower alkylthio group, a lower alkylamino group or a di-lower alkylamino group. ] or a salt thereof; (2) a compound represented by the formula 3,7-dichloro-8-quinolinecarboxylic acid; and (3) a compound represented by the formula 1-(α,α-dimethylbenzyl)-3-(4 - A herbicidal composition characterized by containing a compound represented by (methylphenyl)urea as an active ingredient.