JPS58188804A - Herbicide - Google Patents

Abstract

PURPOSE:A herbicide containing a substituted phenylsulfonylurea derivative and pendimethalin as active constituents, capable of exhibiting more improved synergistic effect on the control of weeds than in use of simple chemicals in a low dose, and capable of controlling completely the weeds by the application once. CONSTITUTION:A herbicide containing a substituted phenylsulfonylurea derivative of formula I [X is O or direct bond; Y is H or Cl; R is formula II (R<1> and R<2> are CH3 or OCH3) or formula III] having improved herbicidal activity and pendimethalin [=N-(1-ethylpropyl)-2,6-dinitro-3,4-xylidine] wellknown as a herbicide as active constituents at (1:10)-(2:1), preferably (1:5)-(1:1), mixing weight ratio. The resultant mixed herbicide has low toxicity and a wide herbicidal spectrum without the phytotoxicity to cultivated plants, particularly paddy rice, exhibits improved residual effect and safety, and is usable particularly as a pre- emergence soil treating agent and foliar and soil treating agent for weeds in paddy fields.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to herbicides exhibiting excellent biological activity.

More specifically, a substituted phenylsulfonylurea derivative represented by the general formula: (wherein, X is an oxygen atom or a single bond, and Y is a hydrogen atom or a chloro atom, represents a group); Ethylglobil) - Muroshi =
) o, (3,'A-xylidine (pendirn)
ethal in.

The present invention relates to a herbicide mixture that is blended with benzo (methalin) to produce a synergistic effect that cannot be expected when applied alone, and is capable of killing many types of problem weeds with a low application rate.

Currently, many herbicides have been put into practical use as herbicides for paddy fields, and are widely used as single agents or mixtures.

However, paddy field weeds are common, and although there are many herbicides that are effective against annual weeds, there are almost no herbicides that are effective against perennial weeds. As a result, the number of perennial weeds has increased, and there is a strong need for their control.

Perennial weeds generally grow vigorously and have a long emergence period, making it difficult to completely control them. Therefore, herbicides are desired to have a broad spectrum of herbicidal properties that can kill many types of weeds.

In addition, recent rice cultivation has rapidly become more mechanized and transplanted earlier, providing a more suitable place for weeds to grow than ever before. It tends to be unpredictable.

For this reason, the same or different herbicides are repeatedly used several times, but this repeated use of herbicides not only requires a great deal of labor, but also causes damage to paddy rice due to large amounts of herbicides being applied. This poses undesirable problems such as soil residue and soil residue.

The applicant of the present application has conducted repeated research and experiments in order to find a new substituted phenylsulfonylurea derivative having superior herbicidal activity.
It has been found that the novel substituted phenylsulfonylurea derivative represented by 1) has excellent selective herbicidal activity (Japanese Patent Application No. 77 and %Gan Shoj Otsu-/≠μ
jri no. 0).

In order to improve these problems of conventional herbicides, the present inventors aimed to completely control all weeds by multiple spraying, have a high degree of safety for paddy rice, and have extremely low toxicity to humans and animals. As a result of repeated research in order to develop a herbicide with a low and safe herbicide, we found that a novel substituted phenylsulfonylurea derivative represented by the general formula (1) that exhibits a specific herbicidal activity and a formula known as a herbicide (see the button) Represented N-(/-ethylglobil)
The present invention was completed based on the knowledge that an excellent herbicide that overcomes these problems can be obtained by blending Zonitro 3 slag with xylidine (pendimethalin).

The herbicide of the present invention exhibits extremely pronounced synergistic and synergistic effects by mixing the herbicides as in the present invention, even at concentrations where each of the constituent single agents would not be sufficiently effective on its own. It has a synergistic effect and exhibits an accurate selective control of weeds, for example, even against weeds with advanced leaf stages (such as weeds that grow at the two-leaf stage of weeds). At the same time, it is possible to achieve sufficiently satisfactory selective control even for grass species for which a single agent has not been shown to be sufficiently effective. Weeds) were confirmed to be acquired. It was also found that the herbicide of the present invention has even better properties in terms of residual effectiveness.

It has been completed since then.

[
Preferred examples of the substituted phenylsulfonylurea derivatives include the following compounds.

Compound No. (1) N-,2-biphenylylsulfonyl, N'-(F-methoxy-6-methyl-pyrimicin-1-yrunurea, m
p/tata~202℃ Compound No. (, riN-21bi7enylsulfonyl, N'-(IIL, ot-zomesolupyrinone-noyl)urea, mp,
203-201°C Compound No. (3) N-2-,yenoxyphenylsulfonyl, N'-(4
t-Methoxy-Methyl-birynone-noyl)urea, mp/R-200℃ Compound number (≠) N-2-(2-chlorophenoxy)phenylsulfonyl, N'-(+1-methoxy- 6-methyl-pyrimicin-2-yl) urea, mp, 2/A~, 2λOC Compound number (J') N-2-phenoxyphenylsulfonyl, N'-(≠,
6-zomethyl-bilygin-noyl) urea, mp
/7J'-/I O℃℃Compound number 6) N-1-biphenylylsulfonyl, N'-(≠-methoxyt-methyl-/, 3J-triazon-2-yl)urea, mp /riO~/73 °C Compound No. (7) N-co-biphenylylsulfonyl, N'-(41, O-dimethoxy-/, 3.3- ) lyazo/-noyl)
Urea, mp/73'~/♂0℃ Compound number (t) N-2-phenoxyphenylsulfonyl, N'-(≠-
Methoxy6-methylome3. ! ;-triazi/-2-
il) Urrea, mp/r! i~/ri0℃ Compound No. (7) N-,2-phenoxyphenylsulfonyl, N'-(≠
, 6-cymethoxy/, 3J-) ryanone-yl) urea, mp/0-il, s°C compound number (10
) N-λ-(2-10ruphenoxy)phenylsulfonyl N/-(Hiroshi, Otsu-dimethoxy-i, 3.s-triazine-noyl)urea, mp20/~, 20≠°C.

The herbicide of the present invention has low toxicity for warm-blooded animals and good selectivity for cultivated plants, that is, it has the characteristics that cultivated plants are not harmed at normal concentrations, so it can be used as a herbicide for weeds. Can be conveniently used for pest control rounding. The word weed is used here in its broadest sense to mean any plant that grows in an undesirable location.

The herbicide of the present invention exhibits excellent selective control efficacy and excellent persistence of efficacy, particularly when used as a pre-emergence soil treatment agent for paddy field weeds or as a foliage and soil treatment agent.

As described above, the mixture of the present invention is excellent in safety, exhibits outstanding herbicidal activity, and exhibits a wide herbicidal spectrum and excellent persistence of efficacy.

For example, as a paddy field weed, botanical name: Latin name: dicotyledonous plant R + etala 1ndiea Ko@b
n*Azena Lindernia Proeumb
＠ni Pb1leox Chi-Bai Ujitough” Ludw
lgja prostrate Roxburgh hillmushiro Potamogeton dimtlnet
us A, Benn Chickweed Elatine tr
landra 5chk monocot millet Echinochloa crus-ga
Ill Beauy.

ar Konagi Monochoria vaglnall
i Pr@sl Matsubai E1@ochar1s 1
eicular1s L.

Kuroguwai El@ocharim Kuroguva
i Ohwi Tamagayatsuri Cyp@rus dif
formis L.

Cyp@-rus s+eroti
nus Rottbo@1 Urikawa S, a, git
,t,aria pygma@a Miq Omodaka
Sagik,,t,aria trifolia L.

Allsma canallcula
tum A, Br, @tBouch・ Firefly 5elrpus juncoide, s,
Roxburgh v*r.

5circus 1insolat
us Franch atSama.

Shizui 5circus etub@rulat
ua koukyara 5c1rpus planie
Herbicidal activity is observed in plants such as ulmis Fr, Schmldt, etc., and it has the characteristic that it has no harmful effect on paddy rice.

When using the herbicide of the present invention, it can be used directly as it is after being diluted with water, or it can be used in various formulations using IkII and adjuvants by methods commonly used in the agricultural chemical manufacturing field. be able to. In actual use, these various preparations can be used directly or diluted with water to the desired concentration before use.
Agrochemical auxiliaries mentioned here include, for example, diluents (solvents, fillers, carriers), surfactants (solubilizers, emulsifiers,
Examples include dispersants, wetting agents), stabilizers, and fixing agents.

Solvents include water: organic solvent; hydrocarbons [e.g. naphtha, petroleum fractions (paraffin wax, kerosene, light oil, middle oil, heavy oil), Hensen, toluene, xylenes], halodanized hydrocarbons [e.g. chloro methylene, carbon tetrachloride, trichlorethylene, ethylene chloride, ethylene dibromide, chlorobenzene, chloroform], alcohol [(
Examples, l, methyl alcohol, ethyl alcohol, clobyl alcohol, ethylene glycol], ethers C Examples, t, ethyl ether, ethylene oxide, dioxane], alcohol ethers [e.g. ethylene glycol]
monomethyl ether], ketones [e.g. acetone, isophorone], esters [e.g. ethyl acetate, amyl acetate], amides [e.g. dimethylformamide, dimethylacetamide], sulfoxides [e.g.
dimethyl sulfoxide].

Inorganic materials such as slaked lime, magnesium lime, gypsum, calcium carbonate, sandstone, peroxide, pumice, calcite, diatomaceous earth, amorphous silicon oxide, alumina, zeolite, clay minerals (e.g. /J?Ilophyllite) can be used as fillers or carriers. , talcum, montmorillonite, beidellite, vermiculite, kaolinite, mica): Vegetable organic substances such as: grain flour, starch, processed starches, sugar, glucose, plant stems - Crushed sea urchin synthetic resins such as: phenolic resin, urea resin, vinyl chloride Examples include resins.

Examples of the surfactant include anionic surfactants; alkyl sulfate esters [for example, lauryl (sodium a-ate)], arylsulfonic acids [for example, alkylaryl sulfonate, sodium alkylnaphthalene sulfonate], Acid salts, polyethylene glycol alkyl aryl ether sulfate salts: cation (
Cationic) surfactants; Alkylamines C e.g. laurylamine, stearyltrimethylammonium chloride, alkylzmethylpensylammonium chloride], polyoxyethylene alkylamines: Nonionic surfactants; polyoxyethylene glycol ethers [e.g. , polyoxyethylene alkylaryl ether, and its condensates),! Examples include ethylene glycol esters (for example, polyoxyethylene fatty 1Vl ester), polyhydric alcohol esters (for example, polyoxyethylene sorbitan monolaurate), amphoteric surfactants, and the like.

Other stabilizers, fixing agents [e.g., agricultural soap, casein lime, sodium alginate, polyvinyl alcohol (
PVA), vinyl acetate adhesive, and acrylic adhesive].

The mixed active compound of the present invention can be manufactured into various formulations by methods generally practiced in the agricultural chemical manufacturing field. Examples of formulation forms include emulsions, oils, wettable powders, suspensions, powders, granules, powders, tablets, capsules, and the like.

This herbicide for sprouting contains 0.7 to 10% of the above mixed active ingredients.
It can be contained in an amount of 0% by weight, preferably 5% by weight.

For practical use, the various formulations and spray preparations described above (r@ady-to-use-pr-par) are available.
The mixed active compound content in (atlon) is generally 0.
07~5% by weight, preferably 0.0! -60 weight- is suitable.

The content of these mixed active ingredients can be appropriately changed depending on the form of the preparation, the method of application, purpose, timing, location, and weed growth status.

The herbicide of the present invention may also be used with other agricultural chemicals, such as insecticides, fungicides, nematicides, antiviral agents, herbicides,
Plant growth regulators, [e.g., organophosphate compounds, carbamate compounds, dithio (or thiol) carbamate compounds, organochlorine compounds, dinitro compounds, organosulfur or metal compounds, antibiotics, substituted diphenyl ether compounds , urea-based compounds, triazine-based compounds] or/and fertilizers, etc. may also be present.

Various formulations or dispersion preparations (r@ady-to-, us@-pr@p
(aration) is the application method commonly used in the field of agrochemical manufacturing: application (e.g., liquid spraying (spraying), dusting, granulation, water surface application); soil application (e.g., soil mixing).
It can be done by etc.

The application amount per unit area is for each active ingredient,
The substituted phenylsulfonylurea derivative of the general formula (1) and the N-(7-nitylglobilfu) of the formula (II),
2. A-dinitro-3,IIL-xylidine (pendimethalin) and 7270 to 227 parts by weight, preferably /
: about OJ to lOk& of mixed active compounds per hectare at a mixing proportion of 5 to 727 parts by weight, preferably / to
≠Yu is used. However, in special cases it is possible, and sometimes even necessary, to exceed or fall below these ranges.

The present invention uses a compound selected from the substituted phenylsulfonylurea derivatives represented by the general formula (1) as an active ingredient, and N-(/-ethylglobil)-, l! , A-dinitro-3,4t-xylidine (pendimethalin), and a diluent (solvent and/or filler and/or carrier) and/or surfactant, if necessary. Herbicidal compositions are provided that include, for example, stabilizers and fixing agents.

Furthermore, the present invention applies to weeds and/or their growth sites the mixed active compounds of the present invention alone or in the presence of diluents <magents and/or fillers and/or carriers) and/or surfactants and, if necessary, A method for controlling weeds is provided in which the above herbicidal composition is mixed with a stabilizer, a stabilizer, and a fixing agent.

Next, the content of the present invention will be specifically explained with reference to Examples.
The present invention should not be limited to this only.

Examples/(granules) 1 part of compound number C3), 5 parts of the compound of formula [1, 29 parts of bentonite (montmorillonite), 4 parts of talc (talc)
3 parts of lignin sulfonate, 2 parts of water, 2 l of water
10~
It is dried in the form of ≠0 mesh granules at 1 l-O to 0°C to form granules. Sprinkle this on weeds and/or their growing areas.

Example 2 (granules) Water was added to a mixture of compound number C7i, part s, 3.5 parts of the compound of formula (If), 3j parts of bentonite (montmolinite), 5 g parts of talc, and 2 parts of lignin sulfonate. , 11 parts were added, kneaded well, and put into an extrusion granulator.
It is made into granules of 70 to 70 ml and dried at ≠0 to jO<0>C to form granules. Sprinkle this on weeds and/or their growing areas.

Example 3 (granules) Clay mineral particles having a particle size distribution of 0.2 to 2II11 were placed in a rotary mixer and dissolved in an organic solvent under rotation, and 1 part of Good Compound No. (10) and the formula ( The compound/part is sprayed and evenly moistened, and then dried at ti, o~jθ°C to form granules.The granules are sprinkled on weeds and/or their growing areas.

Example 4t (granules) 5 parts of the compound of formula (II) and compound number <! :)i
, s part, 3j parts of bentonite (montmorillonite), 7j parts of talc (talc), and 2 parts of lignin sulfonate, 25 parts of water was added and kneaded well, and the mixture was sieved using an extrusion type granulator. , 10-41. It is dried in the form of 0-me, 0-mesh granules at ≠θ~j0°C to form granules. When this was sprinkled on paddy fields where wild grasses were growing around the two-leaf stage at a mixed active ingredient amount of 8.5 kg per hectare, paddy field weeds could be controlled extremely well due to the synergistic effect.

Example (Irrigation agent) Compound number < 3) is part, compound 3j part of formula (II),
Mixture of powdered diatomaceous earth and powdered clay (/:j)≠5 parts, sodium alkylbenzenesulfonate 2 parts, sodium alkylnaphthalenesulfonate formalin condensate 3
1 part is ground and mixed to make a wettable powder. Dilute this with water and
Drop treatment on weeds and/or their growing areas.

Example B (emulsion) Compound number V) 70 parts, compound of formula (If), 20 parts,
0 parts of Astragalus astragalus, 775 parts of methyl ethyl keto, 1 part of polyoxyethylene alkylphenyl ether, and 7 parts of calcium alkylbenzenesulfonate were mixed and stirred to form an emulsion. This is diluted with water and dripped onto weeds and/or their growing areas.

The unexpectedly superior and remarkable efficacy of the mixed active compounds according to the invention can be seen from the following test results when used against cultivated paddy weeds.

Test Example 1 Preparation of a test compound for the control test against paddy field weeds by application in flooded sewage: Using a granulator, the diameters θ, j'
+w1 It was granulated into rod-shaped particles with a length of 7 to 3 m.

Composition ratio (total 100 parts) Each single active compound: /. Part J--j Preoxyethylene alkyl phenyl ether: 2 parts Bentonite 230 parts Talc: 4.2. J-~t6 parts (The increase or decrease in the amount of M is adjusted by increasing or decreasing the amount of talc.)Test method: For the solid stem test, use a tractor to grow the rice at a depth of 20-200 m according to the usual rice cultivation method. plowed the land. Immediately after plowing, the field was flooded with water to a depth of ~100 cm, and the first puddling was performed. Seven to λ days after the first puddling, the final puddling was carried out by further flooding to a depth of approximately 100 yen. Two days after the final plowing, the water depth in the field was adjusted to 2 to 33 cm, and the rice seedlings were grown in a special seedling box using a power rice transplanter (/j day, 1st instar, 5 leaves, plant height/j) ~/7twr) to 1
Three to J plants were transplanted per plant. Immediately after transplantation, a hard glass sheet was used to cover the area of 20 m2 (,2mX/Oy
ra), and each tuber of the test weed was divided into
Current #) 70~. 20 seeds were inoculated on the ground surface at a depth of 2-3 cm. Thereafter, the water depth in the field was maintained at 3 to 100 m for a long period of time.

Seventy days after transplanting paddy rice, the compound prepared as above was applied in water. Four weeks after application of the chemical, the pest control effect was investigated according to the criteria described below.

The evaluation of the effect is when compared to the untreated area: 10: Weed killing rate compared to the untreated area 1oos: l
More than θochi/less than θochig:
Completed 0chi or more, less than 70% 7:
70 inches or more less than rOchi 6=
60- or more, less than 70%:
son, Dagami Otsu less than 0% 4': 4AOts or more j
O'llr un7R3:
30- or more ≠ less than Q%, 2:
20'A or more 30% full/:
10 years old or older, less than 20% Q:
Evaluation of phytotoxicity to paddy rice less than 10 inches r(1)J indicates no phytotoxicity.

The test results are shown in Table 1.

The above test results show the effects of some of the active ingredients of the herbicide of the present invention, and similar tests have shown that other compounds have the same extremely excellent synergistic selective herbicidal effect. show.

The present invention has been explained in detail in the detailed description of the invention, and the present invention can be specifically summarized as follows.

(1) General formula: (wherein, X is an oxygen atom or a single bond, Y is a hydrogen atom or a chloro atom, where R1 and R2 are a methyl group or a methoxy group) Substituted phenylsulfonylurea A compound selected from derivatives and N-(/-ethylpropyl)-,2,A- represented by the formula;
A herbicide characterized by containing dinitro-migishi-xylidine as an active ingredient.

G2) 7270 to 227 parts by weight, preferably 7270 to 227 parts by weight of the general formula (1) ``t-substituted 7 enylsulfonylurea derivative and the N-(/-ethylpropyl)-1,2-dinitose 3,4A-xylidine of the formula (10). ／：j〜／
: 7 parts by weight of the herbicide according to item 7 above.

Q) The amount of the active ingredient is 0.0/-25% by weight, preferably 0.0/-25% by weight. The herbicide according to the above items 1 and 2, containing 60% by weight of Oj-60.

eA A compound selected from the substituted phenylsulfonylurea derivatives of the general formula (I) and N-(/-ethylpropyl)-,2,A-dinitro-3 of the formula (II)
A method for controlling weeds, comprising applying an effective amount of a mixed active compound with , g-xylino/ to weeds and/or their growing areas.

(a) The method for controlling weeds according to the above paragraph, wherein the weeds are paddy field weeds.

C) the application rate of said mixed active compound is 0//ha;
．． 5-10 kg, preferably 7-11 kg. The method for controlling weeds according to item V above.

■ Substituted phenylsulfonylurea 9 conductor of the above general formula (1) and N-(/-ethylglobil)-2,6-sinitro 3.11-- of the above formula (O) on weeds and /l or their growing areas. Said herbicide is applied with xylidine alone or mixed with diluents (solvents and/or extenders and/or carriers) and/or surfactants and, if necessary, e.g. stabilizers, fixing agents. Method for controlling weeds listed in Hiromu / Name of agent Kawahara 1) - Panicle

Claims (1)

[Scope of Claims] A substituted phenylsulfonylurea derivative represented by the general formula: (wherein X represents an oxygen atom or a single bond or an oxy group), and a substituted phenylsulfonylurea derivative represented by the formula: N-(/-etherzolopyl) - ,2,,
g-zoni) +12-. 3.1/L-xylidine,
A herbicide characterized by containing it as an active ingredient.