JPS5920206A - Herbicide - Google Patents

Abstract

PURPOSE:A herbicide containing a substituted phenylsulfonylurea derivative and benzothiazol-2-yloxy-acetic acid N-methylanilide and bentazone, and capable of exhibiting a very remarkable potentiating and synergistic effect in a small amount of application. CONSTITUTION:A herbicide containing a substituted phenylsulfonylurea derivative of formula I [X is O or single bond Y is H or Cl; R is formula II or III(R<1> and R<2> are methyl or methoxyl)], e.g. N-2-biphenylylsulfonyl-N'-(4-methoxy- 6-methylpyrimidin-2-yl)urea, benzothiazol-2-yloxy-acetic acid N-methylanilide of formula IV and 3-isopropyl-3H-2,1,3-benzothiadiazin-4-one-2,2-dioxide (bentazon) of formula V preferably at 1:(75-150):(20-40) weight ratio. USE:Useful as a foliar and soil treating agents for weeds in paddy fields.

Description

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

More specifically, t-substituted phenyl represented by the general formula: (wherein, X is an oxygen atom or a single bond, Y is a hydrogen atom or a chloro atom, and R1 and R2 are a methyl group or a methoxy group) A sulfonylurea derivative, benzthiazole-choyloxy-acetic acid N-methylanilide represented by the formula: (hereinafter referred to as compound (A)), and 3-1 soprovir-3H-2,/, 3- represented by the formula: benz°thiazine-goonco1,2-dioxide (be
ntazone, hereinafter referred to as pentacine. ) as an active ingredient.

The substituted sulfonylurea derivatives represented by the general formula (D), which are seven active ingredients, are
No. 9'17 and Tokugansho,! t 6- //Ill! ;
This is a herbicide described in Publication No. 90.

Ota, Pennzu Chiaso°-Lucoyloxy Vinegar 11N
-Methylanilide [Compound (A) lj, JP-A-34-
/! ;ll'l/, is a herbicide known from Publication No. 2.

In addition, pentacin is a commercially available herbicide, and it is effective when pre-emergent treatment is applied, but when sprayed on foliage during the growing season, it is effective against perennial broad-leaved weeds and perennial weeds such as Cyperus spp. , its residual effect is short and it is not effective against grass weeds. Even against perennial weeds such as Japanese cypress, Japanese cypress, and firefly, the effect decreases at low application rates, and the herbicidal effect significantly decreases in leaky fields (more than 3 crn per 7 days) due to chemical runoff, etc. .

Conventionally, a variety of herbicides with excellent control activity have been developed to control weeds such as field weeds, grasshoppers, perennial broad-leaved fiber grasses, and perennial weeds such as Pinella 4, which have traditionally been considered the most problematic among paddy field weeds. It has been used as an agent and mixture. As a result, as the rice field weeds mentioned above were controlled, competition between weeds decreased, so weeds that could not be adequately controlled with conventional chemicals, such as perennial weeds such as firefly, urikawa, and water cypress, flourished and became less effective for rice cultivation. caused harm.

Therefore, it is necessary to develop a herbicide with a broad killing spectrum that can simultaneously control many types of weeds, such as the above-mentioned perennial herb, annual cattle weed, and broad-leaved weeds. It is desired to develop an excellent herbicide against the weed Cyperus japonica.

Paddy field weeds, such as annual weeds, broad-leaved weeds, and perennial weeds, grow at each comb development stage at the same time.
For this reason, a so-called systematic treatment in which different types of herbicides are sprayed several times at the same time is carried out. Therefore, it is desirable to develop a herbicide that can control different types of weeds at various growth stages by spraying a low-dose herbicide seven times, and a herbicide with a wide range of suitable treatment periods. .

113 and others have conducted intensive research to solve the above problem, and found that when the herbicide of the present invention is used alone in the conventional manner, the herbicide of the present invention, Vr, is accurately determined. Even when applied to grass species that did not have a significant control effect, it has extremely pronounced synergistic and synergistic effects at low application rates.
It has been found that satisfactory selective weed control can be achieved and a wide spectrum of weed control can be obtained. In particular, the herbicide of the present invention has a remarkable synergistic effect in the control of perennial weeds such as Japanese cypress, which are currently difficult to control, even in extremely overgrown paddy fields, as well as in extremely overgrown paddy fields with leaking water. , the herbicidal effect is quick and accurate, there is no phytotoxicity to rice, the effect is sufficient after two treatments, and the effect is sustainable for a long time and can be controlled at a low application rate, making it economical. The problem was solved and the present invention was completed.

Therefore, an object of the present invention is to provide a novel mixture, especially 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 No. (1) N-2-biphenylylsulfonyl, N'-(Il-methoxy-6-methyl-pyrimidine-codyl)urea, m
p/99-202°C Compound number (,2) N-ubiphenylylsulfonino 12, N'-(4, O-dimethyl-pyrimidine-notl) urea, mp 2
03~xogc Compound club activity (3) N-,2-717xyphenylsulfonyl(4-methquin-6-methyl-pyrimidine-norl)urea, r
np/9/, ~. 20 0℃ Compound number (tl) N-, 2-(,2-chlorphenoquine)tubonylsulfonyl, N'-(ll-methoxy-romethyl-bilimin-nozuA.) urea, mp 2 / / ) ~, 2
, 20°C Compound number (Shio) N-λ-phenoxyphenylsulfonyl, N'-(K
,4-dimethyl-pyrimidine-niyl)urea, mp
/ 7 g~/gO℃ Compound number (ro) N-2-Hyenylylsulfonyl, N'-(
tI-methoxy-6-methyl-/, 3. ! ; - Torryojin-2-1) Urea, mp/9 0-793
°C Compound No. (7) N-, 2-biphenylylsulfonyl, N'- (g,
6-Simethoxy/. 3. ! ;-)Ryazine-2-
J1) Urea, mp/75-/g O℃ Compound number (g) N-2-phenoxyphenylsulfonyl, N'-(ll
-methoxy-romethyl-/,3,left-top-1-noazine-
N-diphenoxyphenylsulfonyl NZ -(4
．． 6-Simethoxy/,3,. ! ; triazine-coyl) urea, mp/60~/ly 5℃ Compound No. (10) N-, 2-C2-chlorophenoxy) phenylsulfonyl, N'-(Lin-dimethoxy-7,, 3-triazine - Nozuru) urea, mp. 2. 0/~201
1C.

The herbicide of the present invention has low toxicity to warm-blooded animals and good selectivity to cultivated plants, i.e., for normal f. l
I'. The two-ml culture has the property of being highly phytotoxic, and can be conveniently used for weed control as a weed weed. The word ``seaweed'' here refers to a variety of plants that grow in places that are not attractive in a wide range of terms.
The plant tastes like stone.

1) The herbicide of the present invention, especially when used as a foliar and soil destruction treatment agent for paddy field weeds, exhibits excellent selective control and excellent persistence of efficacy. show.

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

For example, as paddy field weeds, annual weeds such as field weeds, broad-leaved weeds, and perennial weeds have excellent herbicidal activity, and are beneficial to paddy rice without any harmful effects.

When using the herbicide of the present invention, it can be diluted directly with water, or it can be used in the form of a divine preparation by using an agrochemical adjuvant and a force method commonly used in the field of phosphorus production. can be used. For actual use, these various preparations can be used directly as toilet stones or diluted with water to the desired concentration. Examples of agricultural chemical auxiliaries mentioned here include diluents (solvents, fillers, carriers), surfactants (solubilizers, emulsifiers, 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), benzene, toluene, xylenes], halogenated hydrocarbons [e.g., chloro Methylene, carbon tetrachloride, trichloroethylene, 1-F-lene chloride, ethylene tribromide, chlorobenzene, chloroporm], alcohols [e.g. methyl alcohol, ethyl alcohol, furoyl alcohol, ethylene glycol], ethers [ For example, ethyl ether, ethylene oxide, dioxane], alcohol ethers [e.g., ethylene glycol monomethyl ether], ketones [e.g., acetone, dunphorone], esters [e.g., ethyl acetate, amyl acetate], amides [For example, dimethylformamide, dimethylacetamide] and sulfoxides [for example, dimethylformoquine] can be mentioned.

As fillers or phase substances, amorphous materials such as slaked lime, magnesium lime, gypsum, calcium carbonate, silica, pearlite, pumice, calcite, diatomaceous earth, amorphous silicon/I oxide, alumina, zemerite, clay minerals (e.g. 1-f, Hylov 4 Uzuto, Talc, Montmorillona 1to, Bazugera 1to, Vermiculite, Kaolinite, Mica): Vegetable organic substances such as: Flour, starch, processed denzo/, sugar, glucose, plant stems Examples of crushed trunk resins include phenolic resins, urea resins, and vinyl chloride resins.

Examples of surfactants include anionic (one-one) surfactants; alkyl sulfate esters [for example, sodium lauryl sulfate], ryyl sulfonic acids [reportedly alkylaryl sulfonates, sodium alkylnaphthalene sulfonate], Succinate M % Polyethylene glycol alkylaryl ester Nisder sulfate salts: Cationic surfactants; Alkylamines [e.g.
laurylamine, stearyl trimedyl ammonium chloride, alkyldimethylbenzylammonium chloride], polyoxyethylene alkyl amines: nonionic surfactants; polyoxyethylene glycol ethers [e.g., polyoxyethylene alkylaryl ether, Oyohiso's Condensates], polyoxyethylene glycol esters (eg, polyoxyethylene fatty acid ester), polyhydric alcohol esters (eg, polyoxyethylene sorbitan monolaurate), diampholytic surfactants, and the like.

Other stabilizers, fixing agents [e.g., agricultural soap, limestone, sodium alginate, polyvinyl alcohol (
PVA), vinyl acetate adhesives, and allyl adhesives].

The mixed active compounds of the present invention can be manufactured into various formulations by methods generally practiced in the agricultural chemical manufacturing field. The formulation form is emulsion: oil: wettable powder: M
Examples include P clouding agents: powders: granules: powders: tablets: capsules.

The herbicide of the present invention contains 0.0% of the mixed active ingredient. /~700
The content may be heavy, preferably 1 to 93% by weight. .

Actual costs may vary depending on the various preparations mentioned above.
The mixed active compound content in the ratio is generally 0.0/~9S, preferably 0.05~60
A range of weight percent is suitable.

The content percentage of these mixed active ingredients can be appropriately changed depending on the form of the preparation, the application method, purpose, timing, location, and weed outbreak status@1, the herbicide d of the present invention, and if necessary, other agricultural chemicals For example, insecticides, fungicides, nematocides, antiviral agents, herbicides, plant growth regulators, [for example, organic nitsdale phosphate compounds, carbamate compounds,
dithi, 71 (or thiol) carbamate compound,
Organochlorine compounds, dinitro compounds, organic sulfur or metal compounds, antibiotics, diphenyl-teA compounds, urea compounds, triazine compounds] or/
ready-to-use-prepare containing the mixed active ingredients of the present invention, which may also contain fertilizers and the like.
(ratio) refers to the application methods commonly used in the agricultural chemical manufacturing field, such as application methods (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 based on each active ingredient,
For the substituted phenylsulfonylurea aliphatic conductor/substituted portion of general formula (1), benzthiazole-2--1-loxyacetic acid N-methylanilide [Compound (A) 150
~200 parts by weight, 15-40 parts by weight of pentacine, preferably 7 parts of [compound (A)] for the substituted phenylsulfonylurea derivative/weight f) of the general formula (1)
At a mixing ratio of ~/0 parts by weight of pentacine and 20~qO parts by weight, the amount of mixed active compound per hectare is approximately 0.
2~Og shame, preferably 0.3~0. bKy is used. However, in special cases it is possible, and sometimes even necessary, to exceed or exceed these ranges.

Honbun Meiban-1 As active ingredients, a compound reversely refracted from the substituted phenylsulfonylu-17a derivative represented by the general formula (1) and a pendulum acid iN-methyl represented by the formula (n) Contains anilide [compound (A)], penentane, and a diluent (solvent and/or filler and/or phase) and 7
Dimension ii: A herbicidal composition containing a surfactant and, for example, a stabilizer and a fixing agent, is provided.

In addition, weeds and/or their growth (1)
7:l P)t The mixed active compound of the present invention alone, a sweet diluent (solvent and/or filler and/or phase) and/or surfactant, and if necessary, a stabilizer, a fixing agent There is also provided a method for controlling weed, which comprises applying the above herbicidal composition mixed with the above herbicidal composition.

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

Examples/(granules) Compound number (3) 0.01 part, compound of formula (It) (
A) Add 2 parts of water to a mixture of 1 part, 0.33 parts of pentacine, 29 parts of bentonite (montmorillonite), 67.46 parts of talc, and a part of lignin sulfonate, knead well, and extrude to granulate. It is made into granules of 10-tIO mesh by a machine and dried at 70-30°C to form granules. Sprinkle this on grass, grass and/or their growing areas.

Example 2 (granules) Compound No. (7) 0.07 parts, compound of formula (II) (
A) Add 2 parts of water to a mixture of 1 part, 2120.33 parts of hemp, 29 parts of bentonite (montmorillonite), 47.44 parts of talc, and 2 parts of lignin sulfonate, knead well, and extrude. Using a granulator, it is made into 10 to 0 mesh granules and dried at 90 to SO 0 C to form granules.The granules are sprinkled on weeds and/or their growing areas.

Example 3 (granules) Clay mineral particles with a particle size distribution of 0.2 to 2wn 97.3
0.0.2 parts of compound number Cl0), 0.0.2 parts of compound No. Cl0), 2 parts of compound (A) of formula (n), 0.0. Part I, l, is sprayed to evenly moisten and dried at 11 o-soc to form granules. Sprinkle this on the weeds and place a few seeds in the growing area.

Example tJt (Irrigation agent) Compound number (,3) o, 1 part, compound (A) of formula (11)
) 70 parts, 3.3 parts of pentacine, a mixture of powdered diatomaceous earth and powdered clay (/: 5) g/, 1:, parts, liumco part, sodium alkylnaphthalene ponate /L marine condensate,? f
1. Grind and mix to make an irrigation agent. Dilute this with water and
"weeds", ・yohi/weeds or dripping treatment on their growth areas J
Ru.

Example k (emulsion) Compound %) r number-g (7) 0. ．． 2 F'd11, formula (II) (7) Compound (A), 20 parts, pentacine 4.48B, xylene 4tQ parts, methyl ethyl lactone ig, 2m, polyoxyethylene alkylphenyl ether 3 parts, alkylbenzene Seven parts of calcium sulfonate are mixed and stirred to form an emulsion. This is diluted with water and dripped onto 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.

Test Example 1 Control test on paddy field weeds by application in flooded water (chemical treatment after paddy rice transplantation). The field was cleared in spring, and the final planting was done three days later. Three days after the final stage, the water depth in the field was adjusted to /~2 UL, and rice seedlings (15 days old, 2-2. /Left~/7
cm, ) were transplanted at a rate of 3 to S per plant.

Immediately after transplantation, using a hard plastic sheet,
It was divided into m2 (/θIn x 3 m). The depth of water reduction in the field was approximately 3 ctn for 7 days, and the water depth was maintained at 3 to Scm for a long period of time. After paddy rice transfer'la/θE1, 2
After θ days, a drug prepared in the same manner as in Example Ω was applied with water q'T. Two weeks after application of the chemical, the control effect was investigated using late criteria.

The effectiveness rating is 5 when compared to the untreated area! i-: Weed killing rate over untreated area e 9% or more (dead) tl: Weed killing rate over untreated area gθ% or less than 1 in 19 3: Weed killing rate over untreated area SO% or more and less than go%, 2 : Weed killing rate for untreated area 30% or more and less than 0 on the left /: Weed killing rate for untreated area / θ row or more and less than 30% θ: Weed killing rate for untreated area less than 10% (effective) Chemical damage to paddy rice An evaluation of "0" indicates no chemical damage.

The test results are shown in Tables/2.

(1 blank space below) Table 1 Note) Compound number (7) is the same N-,2-biphenylylsulfonyl, N'-(&16-cymethoxy~
/, 3. ! ; −) Reazine-codyl) Indicates urea.

Compound (A) represents the same penzthiazole-dulmexyacetic acid N-methylanilide as described above.

Pentacine is the same 3-ingrovir-3H as described above.
-,1,/,3-penzothiazine-kuonyu, 2-dioxide is shown.

Table 2 Note) Compound 1h (7) is the same N-, 2-
Biphenylylsulfonyl, N'-(q,4-syn)xy/, 3. Left - triazine-suyl) urea is shown.

Compound (A) represents the same penzthiazole-choyloxy-acetic acid N-methylanilide as described above.

Bendazone is the same 3-improvir-3H as described above.
-co,/,3-benzothiazin-q-one 2,2-dioxide.

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

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

(1) General formula: (In the formula, an oxygen atom is removed or immediately bonded to ) T: k b A compound selected from substituted phenylsulfonylurea derivatives and benzthiazole-2-1-loxyacetic acid N represented by
A herbicide comprising -methylanilide and 3-1sopropyl-3H-2,/,3-benzothiazin-q-one λ,2-dioxide represented by the formula: as active ingredients.

(,2) 30 to 200 parts by weight of benzthiazole-2--1-loxyacetic acid N-methylanilide of the formula (II) to the substituted phenylsulfonylurea rust conductor of the general formula (1)/part by weight of the formula (II), 3-Ingropyl-3H-,2,/,3-benzothiazine-guone 2,2-dioxide of (III) to 60 parts by weight, preferably 60 parts by weight of the phenylsulfonylurea derivative of the general formula On the other hand, penztyrozoole-choyloxyacetic acid N-methylanilide 7S-15 of the formula (n)
0 parts by weight, 3-4-bropyl-3H-2 of the above formula (m)
, /, 3-benzothiazin-q-one 2,2-dioxide in a ratio of 20 to '101M3.

(3) The herbicide according to the above items 1 and 2, which contains the active ingredient in an amount of 0.0 to 9% by weight, preferably 0.0s to 40% by weight.

(4') A compound selected from the substituted phenylsulfonylurea derivative of the G formula (1) and the formula (■)
benzthiazole-niyloxyacetic acid N-methylanilide and 3-ingropyru of the above formula (■), ? H-
, 2,/, 3-benzothiazine-q-oz, a method for controlling weeds, which comprises applying an effective amount of a weed control agent mixed with 2-dioxide to weeds and/or their growing areas.

(5) The method for controlling lily grass according to item 9, which is the paddy field weed.

(b) The application rate of the mixed active compound is 0. :l~0-gKy, preferably 0.3~0-b
Kq - A method for controlling weeds according to the above-mentioned paragraphs.

(7) Add the substituted phenylsulfonylurea derivative of formula (1), penzthiazole-choyluochineacetic acid N-methylanilide of formula (11), and the formula (■ ) no 3
-/1 nogrovir-3H-λ,l,3-benzothiazine=guonyu,2-dioxide alone or as a diluent (solvent and/or filler and/or carrier)
and/or applying the herbicide mixed with a surfactant and, if necessary, e.g. a stabilizer, a fixing agent.
Methods for controlling weeds as described in section.

Agent's name: Kawahara 1) - Ho

Claims (1)

[Claims] General formula: (wherein, substituted phenylsulfonylurea conductor,
Penzthiazole-choyluoquine-acetic acid N-methylanilide and 3-1 nbrovir-3H-,:l,/,3-
A herbicide comprising 3 benzothiadiazine-q-onco, 2-dioquinde as active ingredients.