JPS62267205A - Herbicidal composition - Google Patents

Abstract

PURPOSE:To obtain an excellent herbicidal composition, by combining a phenoxypropionic acid derivative and 2-[[(4,6-dimethoxy-pyrimidin-2-yl) aminocarboxyl]aminosulfon-ylmethyl]benzoic acid methyl ester. CONSTITUTION:The objective herbicide composition is a combination of (A) 1pt.(wt.) of a phenoxypropionic acid derivative of formula I [R is 1-6C alkyl or group of formula II (R<1> is 1-6C alkyl)] [e.g. methyl 2-[4-[(5-chloro-2- benzoxazolyl)-oxy]-phenoxy]-propionate, etc.] or its R-enantiomer and (B) 0.06-1.0pts., preferably 0.14-0.5pts. of the compound of formula III. EFFECT:It exhibits extremely excellent selective controlling effect at a low rate of application, has long-acting and residual activity and is free from phytotoxicity to rice plant.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a known phenoxypropionic acid derivative of the below-mentioned formula (1) or its R-enantiomer and the below-mentioned formula (II
) of 2-(((4,6-dimethoxy-pyrimidine-2
-yl)aminocarbonyl]aminosulfonylmethyl]
It relates to an active substance combination with benzoic acid methyl ester having an excellent herbicidal action.

The compound in which R is -CHzSi(CHz)2R' in the phenoxypropionic acid derivative of formula (I) used in the present invention, its R-enantiomer, and their use as a herbicide have already been described in JP-A No. 61-68493. Compounds in which R is an alkyl group, their R-enantiomers, and their use as herbicides are disclosed in JP-A-53-4.
It has already been described in JP-A No. 0767 and JP-A-54-112828.

The above-mentioned active compounds exhibit excellent herbicidal effects against paddy weeds, particularly weeds of the genus family such as Japanese millet, at low doses, but do not exhibit satisfactory herbicidal effects against other paddy weeds.

The 2-((4,6-dimethoxy-pyrimidin-2-yl)aminocarbonyl]aminosulfonylmethyl]benzoic acid methyl ester of formula (II) used in the present invention and its use as a herbicide have already been described. (Unexamined Japanese Patent Publication No. 5
7-112379).

The above-mentioned active compounds exhibit herbicidal activity against annual and perennial weeds, such as grasshoppers, broad-leaved weeds, and bulrushes, but do not exhibit a sufficiently satisfactory herbicidal effect against Japanese millet.

According to the present inventors, (1) In the general formula, R is an alkyl group having 1 to 6 carbon atoms, or C1+
3. represents a group, -C11□-5i-R' (in the formula, R1 represents an alkyl group having 1 to 6 carbon atoms), or a phenoxypropionic acid derivative thereof, or its R-enantiomer and (2 It has been found that a novel active substance combination containing benzoic acid methyl ester as an active ingredient exhibits excellent herbicidal activity.

Japanese millet has traditionally been considered a major weed in rice fields.

Herbicides with various control activities have been developed for the control of annual grass and broad-leaved weeds such as Corygi and bulrushes, and perennial weeds such as Urticaria and Cyperus, and have been used as single agents or mixtures. However, the above paddy weeds are
Herbicides at various developmental stages grow simultaneously, and for this reason, so-called systematic treatments have been implemented in which the same or different herbicides are applied several times. Therefore, problems such as reducing the amount of chemicals used for weed control and saving labor remain. Therefore, it is desirable to develop an excellent herbicide that can control different types of weeds at various growth stages by spraying a low dose of herbicide a few times, and an excellent herbicide that can be used over a wide range of suitable treatment periods. It is rare.

As a result of intensive research aimed at solving the above problems, the present inventors have surprisingly found that the active substance combination according to the present invention containing the active ingredients fl) and (2) individually To show an extremely excellent selective control effect at a low dose by mixing with grass species that did not show sufficient control effect when used in In addition, it has an excellent herbicidal effect over a long period of time during the suitable treatment period, from the beginning of weed emergence immediately after transplanting to the growing season, has a long-lasting effect, has excellent residual effect, and has an excellent herbicidal effect without phytotoxicity to rice. I discovered that it shows.

Phenoxypropionic acid derivatives of the general formula (1) used in the active substance combinations according to the invention, or their R
-Enantiomers are defined as below.

General formula: In the formula, R is an alkyl group having 1 to 6 carbon atoms or a l13 group, CH2Si R' (wherein, R1 is a carbon CH
3 (representing an alkyl group having 1 to 6 atoms), a phenoxypropionic acid derivative and its R-enantiomer.

In the phenoxypropionic acid derivative of general formula (1) or its R-enantiomer, R is preferably an alkyl H3 group or group having 1 to 4 carbon atoms, ClI2 SI R' (in the formula,
R1 preferably represents an alkyl group having 1 to 4 carbon atoms.

Phenoxypropionic acid derivatives of the general formula (1) or their R- used in the active substance combinations according to the invention
Examples of enantiomers include the following compounds.

Methyl 2-(4-((5-chloro-2-benzoxasilyl)-oxy]-phenoxy)-propionate,
Ethyl 2- (4-((5-chloro-2-benzoxasilyl)-oxy]-phenoxy)-propionate, propyl 2- (4-[(5-chloro-2-benzoxasilyl)-oxy]-phenoxy )-propionate, butyl 2- (4-((5-chloro-2-benzoxasilyl)-oxy]-phenoxy)-propionate, iso-butyl 2- (4-((5-chloro-2
-Benzoxacylyl)-oxy)-phenoxy)-propionate, trimethylsilyl-methyl 2- (4
-((5-chloro-2-benzoxasilyl)-oxy]-phenoxy)-propionate, dimethylethylsilyl-methyl 2-(4-((5-chloro-2-benzoxasilyl)-oxy]-phenoxy) -propionate, dimethylpropylsilyl-methyl 2- (4-
((5-chloro-2-benzoxasilyl)-oxy]
-phenoxy)-propionate, dimethylbutylsilyl-methyl 2-(4-((5-chloro-2-benzoxasilyl)-oxy)-phenoxy)-propionate and the R-enantiomer of the above compounds.

The weight ratios of the active substances in the active substance combinations can be varied within a relatively wide range. (per part by weight of active substances of the 11 active substance groups, (2) active substances, e.g.
0.06-1.0 parts by weight, preferably 0.14-0.5
Parts by weight are used.

The active substance combination according to the invention can be used as a selective herbicide for paddy fields, as a pre-emergence soil treatment agent for paddy weeds, and as a foliage and soil treatment agent.

The active substance combinations according to the invention can be used, for example, with respect to the following paddy weeds:

Polygonum: Polygonum, Rorippa, Rot
ala), Lindernia, Bidens, Dopatrlu
m), Ecl 1pta, Elatine, Gra
tiola), Capsicum (order ndernia)
, Lutwigia, Omega
enan the), Ranuncul
us), Rotala, and Deinoste+wa.

(7) (7) 1L1 sashimi: Echino genus
chloa), Panicum, Poa, Cyperu
s), Mono-choria,
Sagittaria (1'iw+bistylis), Sagittaria (Sagittaria), Eleoch (Eleoch)
aris), Scirpus, Alisma, neile
ma), Blyxa, Hoshikuza ([1
riocaulon), Potamog
eton).

The active substance combinations according to the invention can be used in particular with respect to, for example, the following paddy weeds:

Botanical name Latin name Dicotyledonous plant Rotala 1ndica Koeh
ne Azena Lindernia Procum
bens Ph1lcox Ludwig
ia prostrata Roxburgh Potamogeton distincttus
A. Benn Chickweed Elatine tri
andra 5chk seri 0enanth
e javanica monocot I! chinochloa oryzi
cola vasing Konagi Monocho
ria vaginalis Presl matsubai
Old eocharis acicularis L.

Eleocharis Kuroguw
ai Ohwi Cyperus dif
formis L.

Cyperus 5erotinus
Rottboel Urikawa Sagittaria
pygmaea Miq
canaliculatum A, Br, etll (
111CII e Firefly 5circus juncoides
However, the use of the active substance combination according to the invention is in no way restricted to these weeds, but can equally be applied to other weeds.

The active compound mixtures according to the invention can be put into the customary pharmaceutical forms. Such forms include solutions, emulsions, wettable powders, suspensions, powders, soluble powders, granules, suspended emulsion concentrates, and microcapsules in polymeric substances.

These formulations can be manufactured by known methods. Such a process can be carried out, for example, by combining the active compound with extenders, i.e. liquid diluents and/or solid diluents, optionally surfactants, i.e. emulsifiers and/or dispersants and/or foam formers. This is done by mixing using a

When using water as an extender, for example, the organic solvent is
It can also be used as a co-solvent. Liquid diluents include, for example, aromatic hydrocarbons (such as xylene, toluene or alkylnaphthalenes), chlorinated aromatic or chlorinated fatty n-group hydrocarbons (such as chlorohenzenes).

(ethylene chlorides or methylene chloride, etc.), aliphatic hydrocarbons (e.g., cyclohexane, etc. or paraffins (e.g., mineral oil fractions, mineral and vegetable oils, etc.)), alcohols (e.g., butanol, glycols, and their ethers and esters, etc.) ), ketones (such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone), strongly polar solvents (such as dimethylformamide and dimethyl sulfoxide) and water.

Solid diluents include ammonium salts and soil natural minerals (eg kaolin, clay, talc).

Chalk, quartz, akupal guide, montmorillonite,
or diatoms, etc.) and soil synthetic minerals (for example, highly dispersed silicic acid, alumina, silicates, etc.). Solid carriers for granules include crushed and fractionated rocks (e.g. calcite, marble, pumice, sepiolite, dolomite, etc.)
, synthetic powders of inorganic and organic powders, and fine particles of organic substances (
(for example, sawdust, coconut berries, corn cobs, tobacco stalks, etc.).

Emulsifiers and/or foaming agents include nonionic and anionic emulsifiers [e.g., polyoxyethylene fatty acid esters, polio; 1-diethylene fatty alcohol ethers (e.g., alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, arylsulfonates, etc.)] and albumin hydrolysis products.

Suitable dispersants are, for example, lignin sulfide waste liquor and methylcellulose.

Fixing agents can also be used in the formulation (powders, emulsions); fixing agents include carboxymethylcellulose and natural and synthetic polymers such as arahya gum, polyvinyl alcohol, and polyvinyl acetates, etc. Mention may be made of phospholipids (eg cephalins and lecithins) and synthetic phospholipids. Additionally, mineral and vegetable oils can be used as additives.

Colorants may also be used, including inorganic pigments (e.g. iron oxide, titanium oxide and Prussian blue), and organic dyes such as alizarin dyes, ab dyes or metal phthalocyanine dyes, and also , iron, manganese, boron.

Mention may be made of trace elements such as salts of copper, cobalt, molybdenum and zinc.

The formulations generally contain from 0.1 to 95% by weight of the active compound mixture;
The content is preferably 0.5 to 90% by weight.

The active compound mixtures according to the invention can be used for controlling weeds as such or in the form of their preparations, and formulated forms or tank mixtures are also possible.

Mixtures with other known active compounds, such as those normally used in rice fields, such as fungicides, insecticides, plant growth regulators, plant nutrients, soil amendments and other herbicides, are also possible.

The active compound mixtures can be used as such, or in the form of their preparations, or in further diluted application forms, e.g. ready-to-use preparations.
5 solution), emulsions, suspensions, powders, wettable powders and granules. These forms can be prepared using conventional methods such as water spraying.
g) + spraying, agoIIliz
ing) + Can be used by spraying or powdering.

The active substance combinations according to the invention can be applied to the plants before or after emergence.

The amount of active compound applied can vary within a substantial range. The application rate is 0.12-0.5 k of active compound
g/ha, preferably 0.2 to 0.42 kg/ha.

Although each active substance has its weaknesses in herbicidal action,
This platform-use product exhibits a very wide spectrum of weeding that is effective against various weeds, far beyond its mere effects.

The excellent effects of the active substance combination according to the invention can be illustrated in the following examples. However, the present invention should not be limited to this only.

Example 1 Test method 1 for water surface application treatment on paddy field weeds Test method 1 /2,000 are pot (25 x 20 x 9 cm
) was filled with paddy soil and grown at the 2.5 leaf stage (plant height 15cn+).
Three rice seedlings (variety Nihonbare) were planted per pot and transplanted in two locations. Furthermore, we inoculated the seeds of Japanese millet, Japanese cypress, Japanese cypress, Japanese scallop, annual broad-leaved weeds (Azeena, Japanese cypress, Japanese chickweed, Japanese chickweed, Japanese chickweed, etc.), tubers of Japanese cypress, and Japanese cypress, approximately 2 to 3 c.
It was flooded with water. Seven days after transplanting paddy rice, granules prepared from the test compound of the present invention according to Example 3 were treated on the water surface. Approximately 3 after processing
The waterlogged state of CI11 was maintained, and the herbicidal effect and degree of chemical damage were evaluated on a scale of 0 to 5 according to the following criteria three weeks after the chemical treatment.

Evaluation of effectiveness is 5: Weed killing rate 95% or more (withering) compared to untreated area 4:
80% or more but less than 95%38
50% or more but less than 80% 2:
30% or more but less than 50% 1:
10% or more but less than 30% 0:
Less than 10% (no effect) Evaluation of chemical damage to paddy rice compared to untreated area: 5: Phytotoxicity rate over untreated area 90% or more (fatal damage) 4: 50% or more but less than 90% 3: 30% or more Less than 50%2
: 10% or more and less than 30% 1:
More than 0 and less than 10% 0:
It was set as 0% (no chemical damage).

The test results are shown in Table 1.

(Margin below) tl Note) 1) Compound of general formula (1) used in the present invention: Compound (1), 411 is trimethylsilyl-methyl 2-(4
It is the R-enantiomer of ~[(5-chloro-2-benzoxasolyl)-oni-1-oxy]=-soenoxy)-propionate.

N)-11 Compound (1) 421 is ethyl 2-(4-C(5-chloro-2-hendioxazolyl)-oxy]-phenoxy)-propionate.

(1)-+21 2) Compound of formula (1) used in the present invention; Compound (8) is 2-(C(4,6-dimethoxy-pyrimidine-2
-yl)aminocarbonyl]aminosulfonylmethyl]
Benzoic acid methyl ester.

Example 2 (granules) Compound (1) - +211.0 parts, Compound (8) 0.25
25 parts of water was added to a mixture of 30 parts of hentonite (montmorillonite), 66.75 parts of talc, and 2 parts of lignin sulfonate, kneaded well, and made into granules of 10 to 40 mesh using an extrusion granulator. 40~50℃
Dry to make granules.

Example 3 (granules) Crushed mineral particles having a particle size distribution of 0.2 to 2 fins 94.56
of compound (1) dissolved in an organic solvent and 2.0 parts of surfactant were sprayed under rotation.Next, compound (^) and white carbon (1 →-9) Mix 2.5 parts of pulverized bulk powder and make it adhere uniformly to form granules.

Claims (1)

[Claims] 1. (1) General formula: ▲ Numerical formula, chemical formula, table, etc. ▼ (I) In the formula, R is an alkyl group or group having 1 to 6 carbon atoms, ▲
There are mathematical formulas, chemical formulas, tables, etc. ▼ (in the formula, R^1 represents an alkyl group having 1 to 6 carbon atoms), or the phenoxypropionic acid derivative of or its R-enantiomer and the formula (2): ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (II) Containing an active substance combination with 2-[[(4,6-dimethoxy-pyrimidin-2-yl)aminocarbonyl]aminosulfonylmethyl]benzoic acid methyl ester A herbicidal composition characterized by: