JPS62258309A - Herbicidal composition - Google Patents

Abstract

PURPOSE:To obtain a herbicide exhibiting excellent selective herbicidal effect at a low rate of application and having broad margin of application time, by combining a specific phenoxypropionic acid derivative or its R-enantiomer with a specific triazine compound. CONSTITUTION:The objective composition can be produced by using (A) a compound of formula I [R is 1-6C alkyl or group of formula II (R<1> is 1-6C alkyl)] or its R-enantiomer and (B) a compound of formula III (R<2> is 2-5C alkyl) as active substances and compounding 1pt.wt. of the component A with 0.6-10pts.wt., preferably 0.8-4pts.wt. of the component B. The herbicide produced by the above process exhibits extremely excellent herbicidal effect at a low rate of application against weeds to which sufficient herbicidal effect cannot be attained by the separate use of each component A and B. Furthermore, it has a broad margin of application period extending from the germination to the growth stage of the weed, has long-acting activity and excellent residual effect and is useful as a selective herbicide for paddy field, presprouting soil-treating agent for the control of weeds in paddy field and a foliar and soil treating herbicide free from phytotoxicity against rice plant.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to the known compound 7-7-oxypropionic acid derivative of the formula (1) below or its R-enantiomer and the formula (I
The present invention relates to an active substance combination having an excellent herbicidal effect with the known compound I), a trianone compound.

Among the phenoxypropionic acid derivatives of formula (1) used in the present invention, R is -C1(zSi(CHz)2R'),
The R-enantiomer and its use as a herbicide have already been described in JP-A-61-68493. Further, in the compound of chain formula (1), compounds in which R is an alkyl group, their R-enantiomers, and their use as herbicides have already been described in JP-A-53-40767 and JP-A-54-112828. Are listed.

The active compound of formula (I) above shows excellent herbicidal effects against paddy field weeds, especially regular weeds such as Japanese millet grass, at low dosages, but does not show satisfactory herbicidal effects against other paddy field weeds. .

N,N'-diethyl-6-methylthio-113゜5- which is a toIJ7dine compound of formula (II) used in the present invention
Tri7dine-2,4-zyldiamine (cymetrine', s
imetryn) and N-(1,2-methylpropyl)-N'-ethyl-6-methylthio-1,3,5-)riazine-2,4-norrenoamine (dimetamethrin; d
imetbametryn) has already been described as a herbicide (see Vestaside Manual, 7th edition 19).
1983 The Br1tisch Crop
Protection Council 1).

The active compound of formula (II) above exhibits herbicidal activity against paddy field weeds such as weeds (e.g., Japanese grasshopper, Japanese grasshopper, etc.), pine beetle, and A. nigra, but is not satisfactory against Japanese millet and other paddy field weeds. It does not show any weeding effect.

The following general formulas (1) and (2) (1) have been developed by the present inventors: In the formula, R is an alkyl group or group having 1 to 6 carbon atoms.
CHi 10 H2-S i -R' (wherein, R1 is carbon CH
.

a phenoxypropionic acid derivative or its R-enantiomer of (representing an alkyl group having 1 to 6 atoms) and the general formula (2): where R2 represents an alkyl group having 2 to 5 carbon atoms; It has been found that a novel active substance combination containing a toIJ7 compound as an active ingredient exhibits excellent herbicidal activity.

Herbicides with various control activities have been developed for the control of single-handed grass and broad-leaved weeds, such as Japanese grasshopper, grasshopper, and bulrush, which were traditionally considered to be major weeds in paddy fields, as well as perennial weeds, such as turmeric and cyperus. It has been used as a single agent or as a mixture. However, various stages of paddy field weeds grow simultaneously, and for this reason, so-called systematic treatment has been carried out in which the same or different types of herbicides are sprayed several times. Therefore, problems remain to be solved in terms of reducing the amount of chemicals used for weed control and saving labor. Therefore, we need an excellent herbicide that can control different types of weeds at various growth stages by spraying a small amount of herbicide a few times. It is desired to develop an excellent pest control agent with a wide range of properties.

As a result of intensive research aimed at solving the above problems, the present inventors surprisingly found that the active substance combination according to the present invention, which contains the active ingredients (1) and (2) above, is To demonstrate an extremely excellent selective control effect at a low dose, that is, to obtain a broad spectrum, against type V, which did not have a sufficient control effect when used individually with known drugs. In addition, the suitable treatment period has been expanded, and it shows excellent herbicidal effects from the beginning of weed emergence to the weed stage.Furthermore, it has long-lasting effect and excellent residual effect, and can be applied at the initial stage using Tri-7non Kenhokuai. It was discovered that it avoids chemical damage to rice and exhibits excellent herbicidal effects.

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

General formula: In the formula, R is an alkyl group or group having 1 to 6 carbon atoms.
CH.

■ CH2-8i R' (wherein, R1 is carbon CH.

7-functional noxyprobionic acid derivative or its R-enantiomer, which represents a furkyl group having 1 to 6 atoms.

In the 72/xypropionic acid derivative of general formula (1) or its R-enantiomer, R is preferably an alkyl group having 1 to 4 carbon atoms or a group CH.

"CH25i-R' (wherein R1 is preferably carbon CH
.

represents an alkyl group having 1 to 4 elementary atoms).

The phenoxypropion aS conductor of the general formula (I) used in the active substance combination according to the invention or its R-
Examples of enantiomers include the following compounds. Methyl 2-(4-[(5-chloro-2-benzoxasilyl)-oxy]-7eth/oxy)-propionate, ethyl 2-+4-[(5-chloro-2-benzoxasilyl)-oxy] -phenoxy)-propionate, propyl 2-(4-[(5-chloro-2-benzoxasilyl)-oxy 1-phenoxy)-propionate,
Butyl 2-[4-[(5-chloro-2-benzoxasilyl)-oxy 1-phenoxy 1-propionate, iso-butyl 2-+4-[(5-chloro-2-benzoxasilyl)-oxy 1- 72/xy)-propionate, trimethylsilyl-methyl 2-+4-[(5-chloro-2-benzoxasilyl)-oxy 1-phenoxy)-propionate, dimethylethylsilyl-methyl 2-(4-[(5- Chloro-2-benzoxasilyl)-oxy1-phenoxy)-propionate, trimethylpropylsilyl-methyl 2-(4-[(5-chloro-2-benzoxasilyl)-oxy]-phenoxy)
-propionate, dimethylbutylsilyl-methyl 2
-+4-[(5-chloro-2-benzoxasilyl)-
1-phenoxy)-propionate and the R-enantiomer of each of the above compounds.

The general formula (
The trianone compound II) is defined as below.

In the formula, R2 represents an alkyl group having 2 to 5 carbon atoms.

Examples of the durianone compound of the above general formula (II) used in the active substance combination of the present invention include the following compounds.

N,N'-diethyl-6-methyl 1,3゜5-
Triazine-2,4-zirnoamine (cymetrine) N-(1,2-methylpropyl)-N'-ethyl-6
-Methylthio-1,3,5-triazine-2°4-zirnoamine (dimethathrine) The weight ratios of the active substances in the active substance combinations according to the invention can be varied within a relatively wide range. A weight ratio of, for example, 0.6 to 10 parts by weight, preferably 0.8 to 4 parts by weight of the active substance of the active substance group (2) per 1 part by weight of the active substance of the active substance group (1) is exemplified. can do.

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

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

〉 of -Polygonum
), Rorippa, Roripdae (
Rotala), 7xena (L 1ndernia),
B 1 dens, D op
atrium), Eclipta,
E 1aLine, E 1aLine, E 1aLine
Gratiola), Capsicum genus (L 1nd
ernia), Dogwood”/L uduigia
), Oenanthe, Ra
nunculus), Rotala,
Sato Rashii (Deinostema).

Man! l(Ω) Wlyo! Ill: Eehinoc
hloa), Panicum, Poa, Cyperus
, Mon.

choria), F i + * bistyl
is), S agittaria, E Ieocharis, Firefly Jl (3C
irpus), Alis IIla,
Aneilema, Blyx
a), Eriocaulon JIC, H) Ltlh Potamogeton.

The active compound mixture according to the invention can be used in particular with respect to, for example, the following paddy 91 grasses:

Botanical name Latin name Dicotyledonous plant Rotala 1ndica Ko
ehne Azena Lindernia Pro
cumbens Ph1lOx clovetail Ludwigia prostara
ta Roxburgh Hillemushiro P otamogeton dis
tinctus A.

enn Chickweed E Iatine triandra
S chk Seri Oenanthe
javanica monocot Echinochloa oryzic
ola vasing Konagi Monochor
ia vaginalis P rest Matsubai E 1eocharis aciculari
s L.

Kurogwai E Ieocharis K uro
guwai Ohwi Kuma Yatsuri Cyperus
difformis L.

Cyperus 5erotinus
Rottboel Urikawa S agitta
ria pyglIaea M iq A 1isa+a canalieulatum
A.

B r, et B ouche S circus juncoide
However, the use of the active compound mixture according to the invention is in no way limited to these weeds;
It can be applied to other weeds in the same way.

The active compound mixtures according to the invention can be put into customary pharmaceutical forms. In such a form, for example, a liquid agent,
Mention may be made of emulsions, wettable powders, suspensions, powders, soluble powders, granules, suspended emulsion concentrates, 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 can be done by mixing using.

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 (e.g. xylene, toluene or furkylnaphthalene), chlorinated aromatic or chlorinated aliphatic hydrocarbons (e.g. chlorobenzenes, ethylene chlorides or methylene chloride). etc.), aliphatic hydrocarbons M [e.g. cyclohexane etc. or paraffins (e.g. for mineral oil fractions, mineral and vegetable oils etc.), alcohols (e.g. butanol, glycols and their ethers and esters etc.), ketones W (e.g. 7 setone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone), strongly polar solvents (such as dimethyl formamide and dimethyl sulfoxide) and water.

Solid diluents include ammonium salts and soil natural minerals such as kaolin, clay, talc, chalk, quartz, attapulite, montmorillonite, or diatomaceous earth.
and soil synthetic minerals (e.g. 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 granules of inorganic and organic powders, and fine granules of organic substances (e.g. , sawdust, coconut shells, corncobs and tobacco stalks).

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

Suitable dispersants include, for example, lignin sulfide waste liquor and methylcellulose.
(powders, granules, emulsions); such fixing agents include carboxymethyl cellulose and natural and synthetic polymers (e.g. gum arabic, polyvinyl alcohol and polyvinyl acetates, etc.) and natural phospholipids (e.g. Cephalins and lecithins) and synthetic phospholipids. Additionally, mineral and vegetable oils can be used as additives.

Colorants may also be used, including inorganic pigments (such as iron oxide, titanium oxide and Prussian blue), and alizarin dyes, azo dyes or metal 7
Mention may be made of organic dyes such as lyrosinine dyes, and also trace elements such as salts of iron, manganese, boron, 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.

Other known active compounds, such as those commonly used in rice fields, such as fungicides, insecticides, plant growth regulators, plant nutrients, soil conditioners and other herbicides (e.g. 4-(4-
It can also be used as a mixture with chloro-0-tolyloxy)butyric acid, its sodium salt, ethyl ester, and other herbicides.

The active compound mixtures can be used as such, or in the form of their preparations, or in further diluted application forms, e.g. preparations for spraying. ! ! (ready-'to-
use 5 solution), emulsions, suspensions, powders,
It can be used in the form of wettable powders and granules. These forms can be prepared using conventional methods such as liquid spraying (u+a
tering), spraying + ajom
izing), dust or granules.

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. Application rates include 0, 4-1 of active compound,
4 kg/ha, preferably 0.45-0゜95 kg/
An example is an application amount such as ba.

Although the individual active substances have weaknesses in their herbicidal action, the combination according to the invention goes far beyond a mere combination effect and exhibits a very broad herbicidal spectrum effective against a variety of weeds.

The excellent effects of the active substance combinations 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 for application of flooded sewage surface treatment to paddy field weeds 1/2,000 are pot (25 x 20 x 9 cm)
The pots were filled with paddy soil, and paddy rice seedlings (variety Nihonbare) at the 2.5-leaf stage (plant height 15 cm) were planted in 2 locations with 3 plants per pot. In addition, seeds of Japanese millet, Japanese cypress, Japanese grasshopper, annual broad-leaved weeds (such as azalea, Japanese chickweed, Japanese chickweed, Japanese chickweed, Japanese horsefly, etc.), and small pieces of Japanese cabbage were inoculated, and the area was submerged with water to a depth of about 2 to 3 cm. 7 days after transplanting paddy rice,
Granules prepared from the test compound of the present invention according to Example 3 were treated with water. After treatment, maintain a flooded state of about 3 cm, and after 3 weeks of chemical treatment, the herbicidal effect and degree of chemical damage were evaluated to 0 according to the following criteria.
It was graded on a scale of 5 to 5.

Evaluation of effectiveness is 5: Weed killing rate 95% or more (withering) compared to untreated area 4:
80% or more but less than 95% 3: II 50% or more 80
Less than % 2: 30% or more and less than 50% 1: 10% or more and less than 30% 0: II Less than 10% (no effect) Evaluation of chemical damage to paddy rice when compared to untreated area: 5: Rate of chemical damage compared to untreated area 90% or more (fatal damage) 4: II 50% or more 90
Less than % 3: 30% or more and less than 50% 2: tt IQ% or more 30%
Less than 1: 〃 Less than 10% less than 0:
〃 0% (no chemical damage).

The test results are shown in Table 1.

Notes 1) Compound of general formula (I) used in the present invention: Compound (1)-(1) is trimethylsilyl-methyl 2-(4
It is the R-enantiomer of -[(5-chloro-2-benzoxasilyl)-oxy1-7ethoxy)-propionate.

CH.

Compound (1)-(2) is ethyl 2- +4-[(5-
Chloro-2-benzoxasilyl)-oxy]-7e/
xy)-propionate.

2) Compound of general formula (II) used in the present invention: Compound (A) is N,N'-noethyl-6-methylthio-1,
3,5-1 ryanone-2,4-zyldiamine (simetrine).

Compound 4 & I (B) is N-(1,2-dimethylpropyl)-N-ethyl-6-methylthio1,3,5-triazine-2,4-dylcyamine (dimethathrine).

Example 2 (granules) 1.0 parts of compounds (1)-(2), 1.2 parts of compound (B), 30 parts of bentonite (montmorillonite), talc (
Add 25 parts of water to a mixture of 65.8 parts of talc and 2 parts of lignin sulfonate, knead well, make granules of 10 to 40 mesh using an extrusion granulator, dry at 40 to 50°C to form granules. do.

Example 3 (granules) Crushed mineral particles 94 having a particle size distribution of 0.2 to 2 ml1
．． 0.6 parts of compound (1)-(1) dissolved in organic solvent and 2.0 parts of surfactant were added to a rotating mixer.
Spray the area. Next, compound (A) and 3.0 parts of white carbon (i +1 ) crushed powder are mixed and uniformly adhered to form granules.

Claims (1)

[Claims] 1. (1) and (2) below (1) General formula: ▲ Numerical formula, chemical formula, table, etc. ▼ (I) In the formula, R is an alkyl group having 1 to 6 carbon atoms or A phenoxypropionic acid derivative or its R-enantiomer and (2) general formula, which shows the group ▲ mathematical formula, chemical formula, table, etc. ▼ (in the formula, R^1 represents an alkyl group having 1 to 6 carbon atoms) : ▲There are mathematical formulas, chemical formulas, tables, etc.▼ In the formula, R^2 represents an alkyl group having 2 to 5 carbon atoms. A herbicidal composition characterized by containing an active substance combination of triazine compounds.