JPS58188806A - Herbicide - Google Patents

Abstract

PURPOSE:A herbicide, containing a substituted phenylsulfonylurea derivative and O,O-dipropyl-S-2-methylpiperidinocarbonylmethyl phosphorodithioate, etc. as active constituents, and exhibiting potentiating and synergistic action. 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 methyl or methoxyl) or formula III] and O,O-dipropyl S-2-methylpiperidinocarbonylmethyl phosphorodithioate of formula IV or O, O-dimethyl S-[N- (4-chlorophenyl)-N-isopropyl-carbamoylmethyl]-phosphorothioate of formula V. The resultant mixed herbicide has improved safety, exhibits a remarkable herbicidal activity, a wide herbicidal spectrum and lasting improved efficacy, and is suitable particularly to 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 phenyl represented by the general formula; A sulfonylurea derivative and 0,0-dipropyl S-,,2-methylpiperidinolgenylmethyl phosphorodithioate represented by the formula: or 0,0-dimethyl S-[N-(Hiro-chlorophenyl) represented by the formula: )-N-isoglobyl-carpamoylmethyl]
- A herbicide mixture with Phosphrodithiony F [which has a synergistic effect far greater than could be expected when applied alone, and is capable of killing many types of problem weeds with a low application rate. It is related to.

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

However, although there are many herbicides that are effective against multi-organ paddy weeds and annual weeds, there are very few herbicides that are effective against perennial weeds. This has led to an increase in perennial weeds,
There is a strong need for its prevention.

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, recently, the introduction of mechanization and earlier transplantation of rice cultivation have rapidly spread, providing a more suitable place for weeds to grow than ever before, and it is not possible to completely control weeds with multiple herbicide applications. It tends to be unpredictable.

For this reason, the same or different herbicides are used several times, but repeated use of herbicides is not only ``requires a lot of effort'' but also causes damage to paddy rice and soil due to large amounts of herbicides. This raises undesirable issues such as remaining in the country.

The present applicant has conducted repeated research and experiments on substituted phenylsulfonylurea derivatives in order to find novel derivatives with superior herbicidal activity.
It has been discovered that a novel substituted 78-nylsulfonylurea derivative represented by No. 11 has excellent selective herbicidal activity.
IL≠jzQ).

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 low and safe herbicides, we found that a novel substituted phenylsulfonylurea derivative represented by the above general formula (1) that exhibits specific herbicidal activity and a herbicide with the well-known formula l) 0,0-dipropyl8-2-
Methylpiperidinocal is nylmethylphosphorodithioate or 0,0-dimethyl S represented by formula (2)
-[N-(4t-Chloro7,JL-nyl)-N-isogloby-carpamoylmethyl''-phosphorodithioatetra] We believe that an excellent herbicide that improves these problems can be obtained. Chishi completed the invention.

The herbicide of the present invention has extremely pronounced synergistic and synergistic effects by mixing the herbicides as in the present invention, even at concentrations where each of the single agents constituting the herbicide would normally not be sufficiently effective in a single layer. works to provide accurate selective weed control, and for example, its synergistic effect provides significant control even against weeds in advanced leaf stages (e.g., weeds in the 2.J- to 3-leaf stage of wildflowers). At the same time, it achieves sufficiently satisfactory selective control even for car types for which a single agent has not been shown to be sufficiently effective. It was confirmed that weeds such as Shimehotarui and Koraai Yagara were acquired. The herbicide of the present invention was also found to have superior properties in terms of residual effectiveness.

Therefore, an object of the present invention is to provide a novel mixture, particularly a herbicide, and the present invention has been completed based on the above discovery.

Preferred examples of the substituted phenylsulfonylurea derivative represented by the general formula (1) for use in the herbicide of the present invention include the following compounds.

Compound number (1) N-2-biphenylylsulfonyl, r-(g-methoxy-6-methyl-pyrimidin-2-yl)urea, m97
27-202°C Compound No. (2) N-1-bif, nylylsulfonyl, y-(11t, g-
methyl-pyriminone-yl) urea, mp203
~201°C Compound No. (3) N-,2-phenoxyphenylsulfonyl, y-(Hiro~
methoxy6-methyl-pyrimidin-λ-yl) urea, mp/riA ~, 200℃ Compound number (≠) N-λ-(2-10 ruphenoxy) phenylsulfonyl, N'-(≠-methoxy-6 -methyl-pyrimidine-2
-yl) urea, mp, 2/A ~ 220°C Compound number (j) N-λ-7. Tsukidiphenylsulfonyl, "-(Hiroshi, Otsu-dimethyl-pyrimicin-2-yl)urea, mp /
7～/0℃ Compound number (Otsu) N-2-biphenylylsulfonyl, NP-(≠-methoxy-methyl-7,3,3-)ryanone-λ-yl)urea, mp/Y O～ /ri 3℃ compound number (7
) N-2-biphenylylsulfonyl, N'-(≠, A-zomethoxy/, 3.3-) riazone-coyl) urea, mp/76~/IOC Compound number (1') N-2-phenoxy Phenylsulfonyl, ter(Hiro-methoxy-methyl-/, 3.j-)ryanone-λ-
il) urea, mpigz~/ri OC compound number (ri) N-2-phenoxy78ylsulfonyl, so (4t,
A-dimethoxy-/, 3. j -) ryanone-choyl) urea, rap/isO~/gjc compound number (/N-2-C2-chlorophenoxy) phenylsulfonyl, y- (≠, 6-zomethoxy)/, 3.3- triazin-λ-yl)urea, mp, 20/~2011-C
0 The herbicide of the present invention has low toxicity to warm-blooded animals and has good selectivity for cultivated plants, that is, it does not cause any harm to cultivated plants at normal concentrations, so it can be used as a herbicide for weeds. It can be conveniently used for pest control. The term weed here means, in its broadest sense, any plant that grows in undesirable locations.

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 leaf 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 rice field weed, botanical name: Latin name: Dicotyledonous plant Retaiaindlem Koehn * Llnd@rnia Procumb@
nm Ph1laoxchi, Ugitade Ludvigi
a prostrate Roxburgh potamog@ton distlnetus A
,B@nn groove/%cope glutin@triand
ra Sahk Monocot Eahlnochloa
arus-gall B@auv.

V-τ Kosu Gi Monochoria vagln
alis Presl Matsubai El@o@haria
aeiatilaris L.

Kuroguwai El@oehari@Kuroguw&1
0hwi Cyperua dlffor
mla L.

Cyp@rua 5erotinus
Rottbo@1Uri Kawa Sagit
tarim pygmaea Mlq Omodaka Sa
gittaria trifolia L.

Allama eanallculat
um A+Br, 5tBooCh @ Firefly 5eirpti* juncoidas Ro
xburgh war.

Little firefly 5circus lin@olatu
s Frmneh @tS turtle V.

5 tuberu
5circas plani
It has the characteristic that it has herbicidal activity on N. culmis Fr, Sehmidt, etc., but has no harmful effect on n1 paddy rice.

When using the herbicide of the present invention, it can be used directly as it is by diluting it with water, or it can be prepared in various formulations using a method commonly used in the agricultural chemical manufacturing field using agricultural chemical adjuvants. can be used. In actual use, these various preparations may be used directly or
Alternatively, it can be used after being diluted with water to a desired concentration.

The pesticide adjuvants referred to here include, for example, diluents (controlling agents, bulking agents, carriers), surfactants (solubilizers, emulsifiers, dispersants,
(wetting agents), stabilizers, and fixing agents.

Solvents include water: organic solvents; hydrocarbons such as Na7''y', petroleum distillates (paraffin wax, kerosene, light oil, medium oil, heavy oil), benzene, toluene, xylenes], halodanized hydrocarbons. [For example, chlormethylene, carbon tetrachloride, trichlorethylene, ethylene chloride, ethylene dibromide, chlorobenzene, chloroform], alcohol examples, tH, methyl alcohol, ethyl alcohol,
globyl alcohol, ethylene glycol], ethers [e.g. ethyl ether, ethylene oxide, nooxane], alcohol ethers [e.g. ethylene glycol, monomethyl ether], ketones [e.g. acetone, isophorone], esters [e.g. ethyl acetate] , amyl acetate], amide compounds [eg, dimethylformide, dimethylacetamide], and sulfoxides [eg, trimethyl sulfoxide].

Suitable fillers or carriers include minerals such as: slaked lime, magnesium lime, gypsum, calcium carbonate, sandstone, perlite, pumice, calcite, diatomaceous earth, amorphous silicon oxide, alumina, zeolite, clay minerals.

(For example, pyrophyllite, talc, 7/morillonite, beidellite,) 9-Mikijimaite, kaolinite,
Mica): Vegetable organic substances such as: flour, starch, modified starch, sugar, glucose, crushed plant stems, synthetic resins such as: phenolic resin, urea resin, vinyl chloride resin.

Examples of surfactants include anionic surfactants; alkyl sulfate esters [e.g. sodium diuryl sulfate], arylsulfonic acids [e.g. alkylaryl sulfo/dispersed salt, alkyl naphthalene/sodium sulfonate], succinic acid; Salts 1, polyethylene glycol alkylaryl ether sulfate ester salts: Cationic surfactants: Alkylamines [e.g., laurylamine, stearyltrimethylammonium chloride, alkyldimethylbenzyl ammonium chloride], Polyoxyethyl V/Al Keyaki Lua Book ) -: h-ion surfactants; polyoxyethylene glycol ethers (e.g., polyoxyethylene alkylaryl ethers and condensates thereof), polyoxyethylene glycol esters (e.g., polyoxyethylene fatty acid esters), polyhydric alcohols Examples include 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 C]
PVAλ vinyl acetate adhesive, 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. Forms of preparations include: emulsion: oil: wettable powder:
Examples include suspensions, powders, granules, powders, tablets, and capsules.

The herbicide of the present invention contains 0.0% of the mixed active ingredient. /~10
It can contain 0 weight percent, preferably 0 weight percent, preferably 0 weight percent.

In actual use, the various formulations and spray preparations described above (r@ady-to-use-pr@para
The mixed active compound content in the cation) is generally 0.0/
A suitable range is from 75 to 75% by weight, preferably from 0 to 75% by weight.

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 further contain other agricultural chemicals, if necessary.
For example, insecticides, fungicides, nematocides, antiviral agents, herbicides, plant growth regulators, [e.g., organic phosphate compounds, carmate compounds, dithio (t or thiol) carbamate compounds] compounds, organic chlorine compounds, dinitro compounds, organic sulfur or metal compounds, antibiotics, substituted phenyl ether compounds, urea compounds,
It is also possible to coexist with a triathon yarn compound or/and fertilizer.

Woodcutter formulations or spray preparations (r@ady-4o-ug+*-prsp) containing the mixed active ingredients of the present invention
aratlon) can be applied by the application methods and spraying methods commonly used in the manufacturing field in your prefecture [e.g., liquid spraying (spraying),
Powder, granule, water surface application: soil application [for example, soil mixing], etc.

The application amount per unit area is based on each active ingredient,
a substituted phenylsulfonylurea derivative of the general formula (1) and 0,0-zoderovir S-methylpiperidinocal I nylmethylphosphorodithioate of the substitute symbol), or
0,0-trimethyl s -CN-(≠-chlorofminyl)-N-ingropyrucarpamoylmethyl of the above formula]
-With phosphorodithioate/near 0~yo:/! quantity,
Preferably in a mixing ratio of /:j to 3:7 parts by weight, about 0.0.0.0% as mixed active compound per /ha. -~6Ic9,
Preferably 0. 9 is used for lI-~3. However, in special cases, exceeding these ranges may be
or lower is possible, and sometimes even necessary.

The present invention uses a compound selected from substituted phenylsulfonylurea derivatives represented by the general formula (1) and 09O-dipropyl 5-2 represented by the formula ([) as active ingredients.
-Methyl biperitunocarzanyl methyl phosphorozothioate or 0,0-trimethyl S- represented by 2〇
[N-(Hiro-chlorof,nyl)-N-isogloby-carpamoylmethyl]-phosphorodithioate, and a diluent (solvent and/or filler and/or carrier) and/or surfactant, and if necessary,
For example, herbicidal compositions containing stabilizers and fixing agents are provided.

Furthermore, the present invention provides for applying to weeds and/or their growth sites the mixed active compounds of the present invention alone or in the presence of diluents (solvents and/or fillers and/or carriers) and/or surfactants and, if necessary, For example, a weed control method is provided in which the above herbicidal composition mixed with a stabilizer and a fixing agent is applied.

Next, the content of the present invention will be specifically explained using examples.
The present invention should not be limited to this only.

Examples/(Granules) Compound number (3) 7 parts, compound of formula α) 5 parts, bentonite (montmorillonite) Kota part, Merck (talc) l?
1 part, 2 parts of lignin sulfonate, 2.5" of water
20%, knead well, and use an extrusion granulator to produce /θ~
The granules of Hiro O Metsushi are dried at 0-SO°C to form granules. Sprinkle this on weeds and/or their growing areas.

Example 2 (granules) In a mixture of 2 parts of compound number (7), 2 parts of the compound of formula (Company), 35 parts of bentonite (montmorillonite), 7 parts of talc, and 2 parts of lignin sulfonate, water 2
Add the ingredients, knead well, and transfer to an extrusion granulator.10
The product is dried in the form of ~≠0 mesh granules at ≠0-SO°C to form granules. Sprinkle this on weeds and/or their growing areas.

Example 3 (granules) Clay mineral granules having a particle size distribution of 0.2 to 2 degrees were placed in a rotary mixer and dissolved in an organic solvent under rotation.Compound number Cl0) 3 parts, compound of formula (■) / part is sprayed to make it uniformly wet, and then dried at 4tO to jO<0>C to form granules. Sprinkle this on weeds and/or their growing areas.

Example tI- (Granules) Compound tA of formula (II) < z part, and compound number (j
) /, j part, bentonite (montmorillonite) ) JtA part, Merck (talc) j and / part, lignin sulfonate, 2 parts mixture, added to water 23H', well kneaded and extruded. Depending on the granulation machine, 10 to IIL0
It is dried in the form of granules at ≠0 to 0°C to form granules. This is the amount of mixed active ingredient per hectare/77
2. When sprinkled on paddy fields growing around the early J to 3rd leaf stage, paddy field weeds could be extremely well controlled due to the synergistic effect.

Example! (Hydrating agent) Compound tI- of compound number (j)
≠ part, mixture of powdered diatomaceous earth and powdered clay (/1) ju
ts, 2 parts of sodium alkylbenzenesulfonate, and 3 parts of sodium alkylnaphthalenesulfonate formalin condensate were ground and mixed to prepare a wettable powder. This is diluted with water and applied dropwise to weeds and/or their growing areas.

The unexpected superiority and remarkable efficacy of the mixed active compounds of the invention can be seen from the following test results when used against various paddy weeds.

In the test: Preparation of test compound for control test by application to paddy field weeds in submerged sewage: Using a granulator, by the usual granulation method, diameter Q, j
m, length/~j x m.

Composition ratio (700 parts in total) Each single active compound = 7. j-4, ≠ polyoxyethylene alkylphenyl ether:, 2. J part bentonite: 30 parts talc: A 3. / ~ Otsu 6 parts (Increase or decrease in the bulk cap is adjusted by increasing or decreasing the amount of Merck.)Test method: The test field was plowed to a depth of 100 cm using a tractor according to the usual rice cultivation method. I did it. Immediately after plowing, the field was flooded with water from an irrigation canal to a depth of ~λα, and the first puddling was performed. 7 to 2 days after the first plowing,
Further, the area was flooded to a depth of approximately j; cttt and the final puddling was performed. Two days after the final plowing, the water depth in the field was adjusted to 2 to 3 cx, and rice seedlings (lj day old leaf age 2 to Jj leaves, plant height /j to /7 儂) were transplanted at a rate of 3 to 7 plants per 7 plants. Immediately after transplanting, the test weed tubers were divided into sections (20m<2m x 10rn) using hard plastic sheets, and 70 to 2
0 pieces, inoculated at a depth of 2 to 3 cIL below the ground surface. after that,
The water depth in the field was maintained at 3-jcIIL for a long period of time. After 20 days of rice transplantation, the compound prepared as described above was applied underwater. After ≠ weeks of chemical application, the 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 700%: II
20 width or more and less than 700% f: I
More than fO% Less than 7:
# 70 or more, ♂00 copies: 〃 60 width or more, less than 7 parts: I 30 or more, less than 6011 4t: y
tIL04 or more, less than jo-3: I
I 30 or more, less than Hiroo, 2:
I 20 or more 30
Less than regret/: z 10
'lk or more, less than 20 units O: z
Evaluation of chemical damage to paddy rice below 10: ``0''
indicates no drug damage.

The test results are shown in Table 1.

The above test results 1. show the effects of some representative examples 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: (In the formula, or an oxygen atom or a single bond, Y is a hydrogen atom or a chloro atom, where R1 and R2 represent a methyl group or a methoxy group); A compound selected from derivatives and 0#O-no! represented by the formula; Lobil B-2-methylpiperidinocal I nylmethyl phosphorosothioate, or 0,O-dimethyl 8-(N-(≠-chlorophenyl)-N-isogloby-carpamoylmethyl) represented by the formula:
- A herbicide characterized by containing phosphorodithioate as an active ingredient.

(2) E-substituted 78ylsulfonylurea derivative of general formula (I) and 0,0-diglobir S- of the above substitute symbol)
, 2-methylpiperitunocal? Nylmethyl phosphorodithioate or 0,0-nomethyl S of the above formula (2)
-[N-(4t-chlorophenyl)-N-ingroby-carpamoylmethyl]-phosphorodithioate in a ratio of /:10 to ski, preferably /:j to 3:7 parts by weight. The herbicide according to paragraph 1.

(3)! The active ingredients listed in IJ are 0.07 to 7! 3. Herbicide according to paragraphs 1 and 2 above, which preferably contains O,0S-60,tin.

(4) a compound selected from the substituted phenylsulfonylurea derivatives of the preceding fle-general formula (1) and the above-mentioned formula 0
0.0-diglopyr S-,2-methylbiveridinocargenylmethylphosphorodithioate of 1) or target 6
0.0-dimethyl S-[N-(≠-chlorof,nil)-N-isoglobyl-carpamoylmethyl]
- A method for controlling weeds, which comprises applying to weeds and/or their growing sites an effective amount for controlling weeds of a mixed active compound with phosphorodithioate.

(5) The method for controlling weeds according to item ≠ above, wherein the weeds are paddy field weeds.

(6) The method for controlling weeds according to the above paragraph, wherein the application amount of the mixed active compound is O0λ~z#, preferably O0hiro~3 kg per hectare.

(7) 111 on weeds and/or their growing areas;
1 of the substituted phenylsulfonylurea derivative of general formula (1) and the substituted symbol). O-nozolovir S-,2-methylbiperidinocartilylmethylphosphorodithioate,
Or 0,0-dimethyl S-[IN-(4
t-plorophenyl)-N-1-! lobi-carpamoylmethyl]-phosphorodithioate alone or with diluents (solvents and/or fillers and/or carriers) and/or surfactants, and if necessary, e.g.
The method for controlling weeds according to the above-mentioned item 1, which comprises applying the herbicide mixed with a stabilizer and a fixing agent.

Agent's name: Kawahara 1) - Ho

Claims (1)

[Scope of Claims] A substituted 7-enylsulfonylurea derivative represented by the general formula: (in which an X-ray oxygen atom, a single bond, or an oxy group is shown); A herbicide characterized by containing o-diglobir 5-J-methylbiperidinocar-nylmethylphosphorodithioate, or the formula: % methyl]-phosphorodithioate as an active ingredient.