JPS63152303A - Herbicidal composition for paddy field - Google Patents

Abstract

PURPOSE:To obtain the titled composition having excellent herbicidal activity in cultivation of gramineous crops is paddy fields, immediate effects and improved selectivity for weeds and gramineous crops, containing a specific oxybicycloalkane and a specific compound as active ingredients. CONSTITUTION:The titled composition containing an oxybicycloalkane shown by formula I [R is <=14C (substituted) heterocyclic group, aryl or (1-3C alkyl- substituted) 3-10C alicyclic group], especially preferably compound shown by formula II, etc., and [1,3-dimethyl-1-4(2,4-dichloro-3-methyl)benzoyl-5-p- methylbenzoylmethyloxy]pyrazole and/or 2-(2,4-dichloro-3-methylphenoxy) propionanilide as active ingredients and having enlarged proper application period. The active ingredients are blended with a carrier and an auxiliary and made into an agent form such as emulsion, powder, wettable powder, and used.

Description

DETAILED DESCRIPTION OF THE INVENTION Peel ILIL The present invention relates to a herbicidal composition for paddy fields. More specifically, the present invention uses specific oxabicycloalkanes and specific compounds as active ingredients to provide excellent herbicidal activity (wide herbicidal spectrum, etc.) as a herbicidal composition for paddy fields.
The present invention provides products with characteristics such as low phytotoxicity, excellent selectivity between weeds and grass crops, and an expanded application period.

JP-A-58-110591 discloses oxabicycloalkane derivatives and their effectiveness as herbicides for upland fields.

JP-A-57-72903 discloses 4-(2,4-dichloro-3-methylbenzoyl)-1,3-dimethyl-
Herbicides containing 5-phenacyloxypyrazole compounds as active ingredients are disclosed, and JP-A-57-171904 discloses herbicides containing tri- or tetra-substituted phenoxycarboxylic acid anilide compounds as active ingredients. has been done.

The invention relates to a compound of the general formula (I), H2OCH3 (wherein R is a substituted or unsubstituted heterocyclic group or aryl group having up to 14 carbon atoms;
oxabicycloalkanes represented by [1,3-dimethyl-4-(2,4
A herbicidal composition for rice fields containing -dichloro-3-methyl)benzoyl-5-p-methylbenzoylmethyloxy]pyrazole and/or 2-(2,4-dichloro-3-methylphenoxy)propionanilide as an active ingredient. It provides:

The herbicidal composition for paddy fields of the present invention has excellent herbicidal activity (high activity, wide herbicidal spectrum, etc.) in the cultivation of grass crops in paddy fields, and exhibits an extremely rapid onset of herbicidal effect (fast-acting). It exhibits excellent characteristics such as low phytotoxicity to grass crops, excellent selectivity between weeds and grass crops, and an extended application period.

Although the herbicidal composition for paddy fields of the present invention is effective when applied before or after transplanting rice, it is preferable to apply it after transplanting rice because the effect can be fully exhibited.

One component of the compound (referred to as compound A) used as an active ingredient of the herbicidal composition for paddy fields of the present invention is an oxabicycloalkane represented by the following general formula (I). It is a derivative.

Here, R is a substituted or unsubstituted heterocyclic group or aryl group having up to 14 carbon atoms; or C7-
C4l~IQ optionally substituted by 3 alkyl group
It is a group selected from alicyclic groups.

Typical heterocyclic groups include, for example, imidazolyl, triazolyl, thiadiazolyl, 2-quinolinyl, 1-isoquinolinyl, pyronyl, N-methylimidazolyl, N-methylpyrazolyl, and the like.

As an aryl group, a naphthyl group or especially a phenyl group can be exemplified.

Preferred examples of substituents for these heterocyclic groups or aryl groups include lower alkyl groups, chlorine atoms, and fluorine atoms.

The C3-1o alicyclic group is preferably a 03-C6 alicyclic group, such as a cyclopropyl group, a 1-methylcyclopropyl group, a cyclohexyl group, or a cyclo-4=hexenyl group.

R in general formula (I) is preferably substituted with an unsaturated pyridyl group such as a 2-pyridyl group, a phenyl group, or one or two substituents selected from a methyl group, a chlorine atom, and a fluorine atom. It is a phenyl group.

Among the compounds represented by general formula (I), particularly preferred are oxabicycloalkanes represented by the following formula.

H2OCH3 The compound represented by the above general formula (1) includes those exhibiting geometric isomers and optical isomers. The active ingredients used in the herbicidal composition for paddy fields of the present invention may be individual isomers or mixtures thereof.

Other active ingredients used in the herbicidal composition for paddy fields of the present invention are [1,3-dimethyl-4-(2,4-dichloro-3-
Methyl>benzoyl-5-p-methylbenzoylmethyloxirapyrazole (referred to as compound B) and/or 2-(2,4-dichloro-3-methylphenoxy)
Propionanilide (referred to as Compound C).

The usage ratios of Compound A, Compound B, and Compound C are as follows, when Compound A and Compound B are used as active ingredients.
The weight ratio of the active ingredients is Compound A: Compound B = 1: about 5 to about 200, preferably 1: about 10 to about 100, and when Compound A and Compound C are used as active ingredients, Compound A
: Compound C-1: about 2 to about 100, preferably 1: about 5
to about 50, and when Compound A, Compound B, and Compound C are used as active ingredients, Compound A: Compound B: Compound C-1 = about 5 to about 200 = about 2 to about 100, preferably 1: About 10 to about 100: about 5 to 50 is used.

The herbicidal composition for paddy fields of the present invention contains Compound A represented by the above general formula (I), Compound B and/or Compound C as active ingredients, and in addition, known carriers such as clay, talc, etc. , solid carriers such as bentonite and diatomaceous earth,
Alternatively, water, alcohols such as methanol and ethanol, aromatic hydrocarbons such as benzene, toluene and xylene, chlorinated hydrocarbons, ethers, chelons, esters such as ethyl acetate, dimethylformamide, etc. It can be applied by mixing with a liquid carrier such as amides.

Further, if desired, emulsifiers, dispersants, suspending agents, spreading agents, stabilizers, etc. can be added to form any desired dosage forms such as granules, emulsions, wettable powders, and sol preparations for practical use.

The total amount of each of the above-mentioned active ingredients used in the herbicidal composition for paddy fields of the present invention can be appropriately selected within a wide range, and can be exemplified, for example, from about 0.1 to about 99.0% based on the weight of the agent.

The herbicidal composition for paddy fields of the present invention can be applied to paddy fields in any formulation form as described above. The amount of application can be appropriately selected depending on the type of target weed, the time of application, the place of application, the weather, etc., but the amount of the compound represented by the general formula (I) among the active ingredients is, for example, about 0.0% per 10a .1 to about 100g
about 1 to about 30 g, more preferably about 1 to about 30 g.

The herbicidal composition of the present invention can be used in combination with insecticides, fungicides, plant growth regulators, etc., as well as fertilizers, soil conditioners, etc.

The herbicidal composition for paddy fields of the present invention, weeds of the Cyperaceae family such as Novie, Cyperus japonica, Cyperus japonica, etc., Broad-leaved weeds such as Cyperus japonica, Cyperus japonica, Azena, Japanese sphincter, Japanese snail, Japanese cypress, Cyperus cyperus, etc. It exhibits excellent properties that allow it to selectively kill a wide range of weeds, including perennial weeds, without causing any chemical damage to gramineous crops.

In particular, the composition of the present invention may be applied before or after transplanting rice seedlings to paddy fields, but it is preferably applied 1 to 15 days after transplanting rice seedlings.

Production example 1 (±)-2-exo-(2-methylbenzyloxy)-
1-Methyl-4-isopropyl-7-oxabicyclo(
2,2,1) Synthesis of hebutane JP-A-58-11'059
(±)-2-Exo-hydroxy-1-methyl-4-isopropyl-7-oxabicyclo[2,2,1)hebutane was synthesized according to Example 15 of Publication No. 1, and using this, further examples were prepared. Produce the desired (±)-2-exo-(2-methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2,2,1)hebutane according to the method in Section 29. .

The target product was confirmed by NMR1 infrared absorption spectrum, mass spectrum, and gas chromatography.

The obtained target product is an amber liquid with a viscosity of 75 at room temperature.
~90 centiboise (22℃), boiling point 313±2℃ (
760mmHg), density is 1.0141? / 1 (20)
℃).

Example 1 Compound of Production Example 1 (Compound A) 50 parts Compound B
20 parts pheasant roll
50 parts cyclohexanone
Part 20 “Tsurpol 800J (product name, emulsifier)
9 parts were mixed and dissolved to obtain an emulsion. Note that "parts" are based on weight.

Example 2 Compound of Production Example 1 (Compound A) 0.2 parts Compound B 5 parts Bentonite
60 parts talc
After mixing and pulverizing 29.8 parts of dodecylbenzenesulfonic acid sorter, 2 parts of sodium ligninsulfonate, and 3 parts, the mixture was granulated using a granulator in a conventional manner to obtain granules.

Example 3 Compound of Production Example 1 (Compound A) 0.15 parts Compound 8 4 parts Compound C1, 5 parts 2-1 mixture of bentonite and talc 89.35 parts Sodium dodecylbenzenesulfonate 2 parts Sodium ligninsulfonate 3 parts After mixing and pulverizing, the mixture was granulated using a granulator in a conventional manner to obtain granules.

Example 4 Compound of Production Example 1 (Compound A) Part 1 Compound C
A wettable powder was obtained by mixing and pulverizing 10 parts of a 2-1 mixture of gicrite and clay, 84 parts of sodium ligninsulfonate, and 5 parts.

Test Example 1 (Outdoor Concrete Pot Test) Paddy soil was placed in a concrete pot (1 m x 1 m) placed outdoors, mixed with water and stirred to form a paddy field. Then, a certain amount of seeds were sown such as Japanese wildflower, Japanese cypress, Japanese cypress, Japanese cypress, Japanese azalea, Japanese chickweed, etc., and six overwintering buds of Japanese cypress and 6 tubers of Japanese cypress and Japanese cypress were also transplanted. Furthermore, four rice plants at the two-leaf stage were transplanted, with two plants per plant.

The next day, they were gently submerged in water to a depth of 3 cm, and on the 8th day after rice transplantation (1.5 leaf stage of wildflowers), the compound of Production Example 1 (compound A) produced according to Example 2 and [1° 3-dimethyl-
1-(2,4-dichloro-3-methyl)benzoyl-5
The composition of the present invention containing p-methylbenzoylmethyloxirapyrazole (compound B) and/or 2(2,4-dichloro-3-methylphenoxy)propionanilide (compound C) as an active ingredient, Chemical treatments were performed in the amounts shown in 1.

In addition, water leakage treatment was carried out at 2 to 3 am/day for 2 days after the chemical treatment, and from 3 days later, each plant was grown under submergence method 30I11.

Forty days after the chemical treatment, the herbicidal effect on each weed and the chemical damage to rice were expressed in numerical values and codes according to the following criteria. The test results are shown in Table-1.

Standard 1"1" 5 Remaining amount of grass 0%4
Same as above 1-10%3 Same as above
11-20%2 Same as above 21-4
0%1 Same as above 41-60%0 Same as above
Upper: 61% or more, 11%, and 11%.Evaluation was made as follows, assuming that the untreated drug damage rate was 0%.

-Harmless 0% ± Slight 1-10% + Small 11-30% +10 Medium Harm 31-50% ++10 Major Harm 51% or more Test Example 2 Water was poured into a 12cm diameter porcelain pot filled with paddy soil. The rice fields were made into paddy fields, and firefly seeds were sown.

The pot was placed in a greenhouse at 20 to 25°C, and the firefly was grown until it had 1.0 leaf, and treated with aqueous solutions of each hydrating powder of Compound A, Compound B, and Compound C to a predetermined dose. . Thereafter, they were grown in the same greenhouse for 30 days, and the remaining fireflies were taken out, washed with water, air-dried, weighed, and compared with the untreated group.The results are shown in Tables 2 and 3.

Table-2 Mixing effect (%) of compound A and compound B Note: The numbers for compounds A and B are (a, i, g/10a) where,
QE: Expected Asakusa rate, QA2 Asakusa rate of Compound A, QB: Expected Asakusa rate of Compound B).

From this result, the actual Asakusa rate in the plot where Compound A and Compound B were mixed is smaller than the expected Asakusa rate obtained from Colby's formula. For example, the Asakusa rate for Compound A4f/10a is 88.3%, and the Asakusa rate for Compound B200y/10a is 23.8%. The expected Asakusa rate when these are mixed is 21.0% according to Colby's formula. However, in reality, it is 0% and is completely dead.

From these facts, a synergistic effect is clearly recognized by mixing Compound A and Compound B.

Table 3 Mixing effect (%) of Compound A and Compound C Note: The numbers for Compounds A and C are (a, i, g/10a) The numbers (%) shown in parentheses in Table 3 are , Q: expected Asakusa rate, QA: Asakusa rate of compound A, Qo: expected Asakusa rate of compound C).

From this result, the actual Asakusa rate in the plot where Compound A and Compound C were mixed is smaller than the expected Asakusa rate obtained from Colby's formula. For example, the Asakusa rate for Compound A41F/10a is 88.3%, and the Asakusa rate for Compound C20g/10a is 35.2%.

The expected remaining grass rate when these are mixed is 31.1% according to Colby's formula. However, in reality, it is 0% and is completely dead.

From these facts, a synergistic effect is clearly recognized by mixing Compound A and Compound C.

Claims (1)

[Claims] General formula (I), ▲Mathematical formula, chemical formula, table, etc.▼...(I) (In the formula, R is a substituted or unsubstituted heterocyclic group having 14 or less carbon atoms. group or aryl group; or C_1
_～_3 C_3 optionally substituted by an alkyl group
Oxabicycloalkanes represented by _～_1_0 (represents a group selected from alicyclic groups) and [1,3-dimethyl-4-(2,4-dichloro-3-methyl)benzoyl-
5-p-methylbenzoylmethyloxy]pyrazole,
and/or a herbicidal composition for rice fields containing 2-(2,4-dichloro-3-methylphenoxy)propionanilide as an active ingredient.