JPH06145012A - Herbicide containing oxazolone derivative, bromobutide and the like - Google Patents

Abstract

PURPOSE:To provide the novel herbicide composition containing a specific oxazolone derivative, (R,S)-2-bromo-N-(alpha,alpha-dimethylbenzyl)-3,3-dimethylamide, etc., having an excel lent herbicidal activity and used for paddy fields. CONSTITUTION:The herbicide comprises both an oxazolone derivative of formula I (R is 3-4C alkynyl, tetrahydropyran-3-yl or tetrahydrofuran-3-yl which may be substituted with one or two methyl groups) (e.g. the compound wherein R is -CH2CidenticalCH) and (R,S)-2-bromo-N-(alpha,alpha-dimethylbenzyl)-3,3- dimethylbutyramide or 1-(2-chlorobenzyl)-3-(alpha,alpha-dimethylbenzyl)urea. The herbicide can perfectly control all weeds by its once application, and can expand its application suitable period without deteriorating its safety for paddy fields. The herbicide exhibits the synergistic effect, and its effect duration is long. The compound of formula I is obtained from a compound of formula II through five processes.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a novel paddy herbicide composition having excellent herbicidal activity.

More specifically, the general formula (I)

[0003]

[Chemical 2]

(Wherein R is a C ₃ -C ₄ alkynyl group, 1
Or an oxazolone derivative represented by a tetrahydropyran-3-yl group which may be substituted with two methyl groups or a tetrahydrofuran-3-yl group (hereinafter abbreviated as compound (I)), and (R, S) -2. -Bromo-N-
(Α, α-Dimethylbenzyl) -3,3-dimethylbutyramide [abbreviated as compound (A) below] or 1- (2-chlorobenzyl) -3- (α, α-dimethylbenzyl) urea [compound below ( Abbreviated as B)].

[0005]

2. Description of the Related Art At present, many herbicides have been put into practical use as paddy herbicides and widely used as single and mixed agents.

However, there are many kinds of paddy weeds,
In addition, the germination and growth time of each weed is not uniform, and the occurrence of perennial weeds is particularly long. Therefore, it is very difficult to control all weeds with one application of herbicide. Therefore, as a herbicide, it can kill many kinds of weeds including annual weeds and perennial weeds, that is, it has a broad herbicidal spectrum, is effective for well-developed weeds, and can maintain the weeding effect for a certain period of time. The emergence of highly safe drugs for paddy rice is most desired.

Compound (I), which is one of the active ingredients of the present invention, is a known herbicidally active compound described in WO9212139. Another active ingredient, (R, S) -2-bromo-N- (α, α-dimethylbenzyl) -3,3-dimethylbutyramide (compound (A)), is a known herbicidal activity known as bromobutide. A compound, and 1- (2
-Chlorobenzyl) -3- (α, α-dimethylbenzyl) urea (Compound (B)) is described in JP-A-60-17291.
It is a known herbicidally active compound described in JP-A-0.

However, the composition of the present invention is a novel combination which has not been described in the literature, and, of course, nothing mentions its specific potentiation.

[0009]

The compound (I) has an effect on annual weeds and broad-leaved weeds in the paddy fields, without causing any phytotoxicity to the paddy rice. However,
When the weeds are treated to a certain extent when they grow to some extent, their effects are reduced, and the effects particularly on Nobie are insufficient. In addition, it is active against firefly and Urikawa, but it causes phytotoxicity to paddy rice at a dose that completely kills it.

On the other hand, the compound (A) exhibits an extremely excellent effect on firefly, which is a highly damaging weed in paddy fields, and also before the occurrence of Nobie, annual weeds, and perennial weeds such as Pleurotus cornucopiae and Pine. Effective in processing. However, the treatment is not effective enough when the weeds are growing. On the other hand, the compound (B) shows a high effect on the paddy field weeds such as Nobie, annual broad-leaved weeds, firefly and pine nuts, by the pre-emergence treatment, but the effect is reduced by the treatment at the time when the weeds grow.

The present inventors have aimed to improve the above-mentioned problems of conventional herbicides, completely control all weeds by one spraying, and have a high degree of safety against paddy rice. As a result of continuing the search for safe herbicides with extremely low toxicity, it was found that an excellent herbicide with these problems improved can be obtained by combining two kinds of active ingredients, and the present invention was completed.

[0012]

[Constitution of the invention]

[0013]

The present invention has the general formula (I)

[0014]

[Chemical 3]

(Wherein R is a C ₃ -C ₄ alkynyl group, 1
Or an oxazolone derivative represented by a tetrahydropyran-3-yl group which may be substituted with two methyl groups or a tetrahydrofuran-3-yl group, and (R,
S) -2-Bromo-N- (α, α-dimethylbenzyl)
A herbicide composition for paddy fields containing -3,3-dimethylbutyramide or 1- (2-chlorobenzyl) -3- (α, α-dimethylbenzyl) urea.

Representative examples of the compound (I) of the present invention are shown in Table 1, but the compound represented by the general formula (I) is not limited thereto.

[0017]

[Chemical 4]

[0018]

[Table 1]

The method for producing the compound (I) is shown below.

[0020]

[Chemical 5]

(Step A) 5-t-butyl-3- [4-chloro-2-fluoro-5
-(2-Methoxyethoxymethoxy) phenyl] -4-
Preparation of Oxazolin-2-one (III) Ethyl N- [4-chloro-2-fluoro-5- (2-
A solution of 3.59 g (11.6 mmol) of methoxyethoxymethoxy) phenyl] carbamate (II) and 1-bromo-3,3-dimethyl-2-butanone (2.60 g) in dimethylformamide (DMF) was charged with lithium bis (trimethylsilyl) amide ( 24.56 ml) (1 mol tetrahydrofuran (T
HF) solution) was slowly added dropwise at room temperature. After stirring for 30 minutes, the mixture was poured into water and extracted with ethyl acetate. Dry the extract
(MgSO ₄ ), concentrated, and the residue was purified by silica gel column chromatography to obtain 3.52 g (84.4%) of compound (II
I) was obtained as an oil.

NMR (200MHz, CDCl ₃ ) 7.46 (d, 1H, J = 6.9Hz), 7.17 (d, 1H, J = 10.0Hz), 6.31 (d, 1
H, J = 2.4Hz), 5.24 (s, 2H), 3.75-3.95 (m, 1H), 3.45-3.65
(m, 2H), 3.33 (s, 3H), 1.24 (s, 9H). (Step B) 5-t-butyl-4,5-dichloro-3- [4-chloro-2-fluoro-5- ( Preparation of 2-methoxyethoxymethoxy) phenyl] -1,3-oxazolidin-2-one (IV) 5-t-butyl-3- [4-chloro-2-fluorophenyl-5-prepared by the method of Step A Chlorine gas was blown into a carbon tetrachloride solution of (2-methoxyethoxymethoxy) phenyl] -4-oxazolin-2-one (III) (51.10 g) at room temperature for 4 minutes. The reaction solution was stirred for 10 minutes, poured into saturated sodium bicarbonate water, and extracted with ethyl acetate.
The extract was dried (MgSO _4), concentrated and the residue was purified by silica gel column chromatography, 31.37 g (60.8
%) Of compound (IV) as an oil.

NMR (60 MHz, CDCl ₃ ) 7.12-7.41 (m, 2H), 6.24 (s, 1H), 5.28 (s, 2H), 3.75-3.95
(m, 2H), 3.42-3.70 (m, 2H), 3.36 (s, 3H), 1.25 (s, 9H). (Step C) 5-t-butyl-4-chloro-3- [4-chloro- 2-
Preparation of fluoro-5- (2-methoxyethoxymethoxy) phenyl] -4-oxazolin-2-one (V) 5-t-butyl-4,5-dichloro-3- [4-] prepared by the method of Step B Chloro-2-fluoro-5- (2-methoxyethoxymethoxy) phenyl] -1,3-oxazolidin-2-one (IV) (3.33 g) in dimethylsulfoxide (DMSO) solution was added to 1,8-diazabicyclo at room temperature. [5,4,0] Undec-7-ene (11.2 ml) was slowly added dropwise. After stirring for 30 minutes, the reaction solution was poured into water and extracted with ethyl acetate. The extract was dried (MgSO ₄ ) and concentrated, and the residue was purified by silica gel chromatography to give 2.41 g (78.8%) of compound (V).

NMR (200MHz, CDCl ₃ ) 7.28 (d, 1H, J = 8.7Hz), 7.24 (d, 1H, J = 6.5Hz), 5.35 (m, 2
H), 3.81-3.90 (m, 2H), 3.51-3.59 (m, 2H), 3.35 (s, 3H),
1.34 (s, 9H). (Step D) 5-t-butyl-4-chloro-3- (4-chloro-2-
Preparation of Fluoro-5-hydroxyphenyl) -4-oxazolin-2-one (VI) 5-t-butyl-4-chloro-prepared by the method of Step C
3- [4-chloro-2-fluoro-5- (2-methoxyethoxymethoxy) phenyl] -4-oxazoline-2
Trifluoroacetic acid (3.10 ml) was added to a methylene chloride solution of -one (V) (2.19 g) at room temperature, and then the mixture was stirred at 60 ° C for 2 hours. The reaction solution was poured into saturated sodium bicarbonate water and extracted with ethyl acetate. The extract was dried (MgSO _4), concentrated, and the residue was purified by silica gel chromatography, 1.55 g (90.1
%) Of compound (VI).

Melting point 170-171.5 ° C. NMR (60 MHz, CDCl ₃ ) 7.19 (d, 1H, J = 9.0 Hz), 6.91 (d, 1H, J = 7.0 Hz), 6.36
(S, 1H), 1.37 (s, 9H). (Step E) In this step, the compound (VI) produced by the method of Step D is used as a starting material in the presence of a solvent, a reaction auxiliary agent and a group R. Is a step of producing compound (I) by reacting with the reactive derivative of.

The reaction aid used in this step may be either acidic or basic and depends on the chemical properties of the above reactive derivative.

When the reaction aid is basic, for example, triethylamine, tributylamine, diethylisopropylamine, pyridine, 1,4-diazabicyclo [2,2]
2,2] octane, 1,8-diazabicyclo [5,4,4]
0] organic tertiary amines such as undecene, sodium hydride, calcium hydride, sodium, lithium,
n-butyllithium, lithium diisopropylamide,
It is an alkali metal base such as lithium bis (trimethylsilyl) amide or potassium t-butoxy, or an inorganic base such as sodium hydroxide, potassium hydride, sodium carbonate or potassium carbonate, and preferably sodium hydroxide or potassium carbonate.

In this case, suitable reactive derivatives are, for example, halides and sulfonates of group R, preferably chloro, bromo, mesyloxy and tosyloxy groups of group R. More preferably, they are a chloro body, a mesyloxy body and a tosyloxy body.

The amount of the reaction aid used is usually 1 to 20 times equivalent, preferably 2 to 10 times equivalent to the compound (VI).

The reaction is preferably carried out in the presence of a solvent, and the solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting material to some extent.
Preferred are hydrocarbons such as hexane, petroleum ether, benzene and toluene, halogenated hydrocarbons such as chloroform and methylene chloride, ethers such as ethyl ether and tetrahydrofuran, N, N-dimethylformamide and the like. Amides, sulfoxides such as dimethyl sulfoxide, nitriles such as acetonitrile, and mixtures of these solvents, more preferably N, N-dimethylformamide.

The reaction temperature is usually -70 to 150 ° C, preferably room temperature to 120 ° C. The reaction time varies depending mainly on the reaction temperature, the raw material compound, the reaction reagent or the type of solvent used, but is usually 15 minutes to 1 day and night, preferably 30 minutes to 4 hours.

When the reaction aid is acidic, for example, inorganic bases such as hydrochloric acid and sulfuric acid, trifluoroacetic acid, acetic acid, p-toluenesulfonic acid, methanesulfonic acid, trifluoromethanesulfonic acid, pyridine p-toluenesulfonic acid. Organic acids such as salts are preferable, and p-toluenesulfonic acid and p-toluenesulfonic acid pyridine salt are preferable.

In this case, suitable reactive derivatives are, for example, olefins in which some of the radicals R have been desaturated.

After completion of the reaction in this step, the reaction target product is collected from the reaction mixture by a conventional method. For example, it can be obtained by adding an organic solvent immiscible with water to the reaction mixture, washing with water, and distilling off the solvent. The obtained target compound is further purified, if necessary, by a conventional method, for example, recrystallization, reprecipitation, chromatography and the like.

Next, a manufacturing example of this step will be described.

5-t-butyl-4-chloro-3- [4-
Chloro-2-fluoro-5- (2-propynyloxy)
Preparation of Phenyl-4-oxazolin-2-one 5-t-butyl-4-chloro-3- (4-chloro-2-
A solution of fluoro-5-hydroxyphenyl) -4-oxazoline-2-one compound (VI) (0.36 g) in dimethylformamide (DMF) was added at 0 ° C. under argon gas to sodium hydride (45 mg) (60% oil dispersion). Reagent) was added to a dimethylformamide (DMF) suspension. 10
After stirring for 1 minute, propargyl bromide (118 ml) was added. After stirring at room temperature for 3 hours, the mixture was poured into water and extracted with ethyl acetate. The extract was concentrated and purified by silica gel column chromatography to obtain 320 mg (80.9%) of the desired product.

Melting point 84-85 ° C NMR (200MHz, CDCl ₃ ) 7.33 (d, 1H, J = 8.9Hz), 7.07 (d, 1H, J = 6.5Hz), 4.81 (dd, 1)
H, J = 2.4,15.0Hz), 4.76 (dd, 1H, J = 2.4,15.0Hz), 2.60 (t,
1H, J = 2.4Hz), 1.37 (s, 9H). The synergistic effect of the present invention is observed in a wide range of mixing ratios, and compound (A) and (B) are added to 1 part by weight of compound (I). A useful herbicide can be obtained by mixing at a ratio of 0.5 to 10 parts by weight.

The composition of the present invention may be sprayed on the drug substance itself, or may be mixed with a carrier and, if necessary, other auxiliary agents to prepare a formulation form usually used as a herbicide, such as powder or coarse powder. , Fine granules, granules, wettable powders, emulsions, aqueous suspensions, wettable granules, oil suspensions and the like.

Suitable solid carriers used for preparing the herbicide of the present invention include clays represented by kaolinite group, montmorillonite group or attapulgite group, talc, mica, pyrophyllite, pumice, vermiculite, Gypsum, calcium carbonate, dolomite, diatomaceous earth, magnesium lime, apatite, zeolite, anhydrous silicic acid, inorganic substances such as synthetic calcium silicate, soybean flour, tobacco flour, walnut flour, wheat flour, wood flour, starch, crystals Vegetable organic substances such as cellulose, coumarone resin, petroleum resin,
Examples thereof include synthetic or natural polymer compounds such as alkyd resins, polyvinyl chloride, polyalkylene glycols, ketone resins, ester gums, cobal gums, dammal gums, waxes such as carnauba wax and beeswax, and urea.

Suitable liquid carriers include paraffinic or naphthenic hydrocarbons such as kerosene, mineral oil, spindle oil and white oil, aromatic hydrocarbons such as benzene, toluene, xylene, ethylbenzene, cumene and methylnaphthalene, and tetrachloride. Carbon, chlorinated hydrocarbons such as chloroform, trichloroethylene, monochlorobenzene, O-chlorotoluene, dioxane, ethers such as tetrahydrofuran, acetone, methyl ethyl ketone,
Ketones such as diisobutyl ketone, cyclohexanone, acetophenone, and isophorone, ethyl acetate, amyl acetate, ethylene glycol acetate, diethylene glycol acetate, dibutyl maleate, esters such as diethyl succinate, methanol, n-hexanol, ethylene glycol, dietine glycol , Cyclohexanol, alcohols such as benzyl alcohol, ethylene glycol ethyl ether, ethylene glycol phenyl ether, diethylene glycol ethyl ether,
Examples thereof include ether alcohols such as diethylene glycol butyl ether, polar solvents such as dimethylformamide and dimethylsulfoxide, and water.

Surfactants used for the purposes of emulsification, dispersion, wetting, spreading, binding, disintegration control, active ingredient stabilization, fluidity improvement, rust prevention, etc. are nonionic, anionic, cationic. Either ionic or zwitterionic may be used, but normally nonionic and / or anionic ones are used. Suitable nonionic surfactants include:
For example, lauryl alcohol, stearyl alcohol, those obtained by polymerizing addition of ethylene oxide to higher alcohols such as oleyl alcohol, isooctylphenol, those obtained by polymerizing addition of ethylene oxide to alkylphenols such as nonylphenol, butylnaphthol,
Polymerized addition of ethylene oxide to alkylnaphthol such as octylnaphthol, polymerized addition of ethylene oxide to higher fatty acids such as palmitic acid, stearic acid and oleic acid, monoesters of these nonionic surfactants and phosphoric acid , Mixtures of diesters and triesters or sulfuric acid esters and salts thereof, those obtained by polymerizing addition of ethylene oxide to amines such as dodecylamine and stearic acid amide, higher fatty acid esters of polyhydric alcohols such as sorbitan, and addition of ethylene oxide thereto. And those obtained by polymerizing addition of ethylene oxide and propylene oxide. Suitable anionic surfactants include, for example, sodium lauryl sulfate, alkyl sulfate ester salts such as oleyl alcohol sulfate amine salt, sodium dioctyl sulfosuccinate, sodium isopropylnaphthalenesulfonate, sodium methylenebisnaphthalenesulfonate, Examples thereof include aryl sulfonates such as sodium lignin sulfonate and sodium dodecylbenzene sulfonate.

Further, the herbicide of the present invention contains casein, gelatin, for the purpose of improving the properties of the preparation and enhancing the biological effect.
High molecular compounds such as albumin, glue, sodium alginate, carboxymethyl cellulose, methyl cellulose, hydroxyethyl cellulose, polyvinyl alcohol and the like and other auxiliary agents can be used together.

The above-mentioned carrier and various auxiliary agents are appropriately used alone or in combination depending on the purpose, taking into consideration the dosage form of the preparation, the application scene and the like.

Dusts are usually prepared by using, for example, 1 part of the active ingredient compound.
To 25 parts by weight, the balance being a solid carrier.

The wettable powder usually contains, for example, 25 to 90 parts by weight of the active ingredient compound, and the balance is a solid carrier and a dispersion wetting agent, and if necessary, a protective colloid agent, a thixotropic agent, an antifoaming agent and the like. Added.

Granules are prepared by, for example, adding 1 of the active ingredient compound.
To 35 parts by weight, the balance mostly solid carrier. The active ingredient compound is either uniformly mixed with the solid carrier, or is uniformly fixed or adsorbed on the surface of the solid carrier, and the particle diameter is about 0.2 to 1.5 mm 2.

Emulsions usually contain, for example, the active ingredient compound 5
Content of about 5 to 20 parts by weight
Part by weight emulsifier is included, the rest is liquid carrier, and rust inhibitor is added if necessary.

[0048]

[Examples] Examples of blending the present herbicide are shown below as Examples.

[0049]

Example 1 (Granule) 1.5 parts of compound (I) -1, 10 parts of compound (B), 64.3 parts of calcium carbonate powder (manufactured by Adachi Lime Co., Ltd.), bentonite powder (Toyosumi Mining Co., Ltd.) Hotaka stamp made by 20),
Amicol No. 1 part (Nippon Kagaku Kogyo Co., Ltd. dextrin) 1.5 parts was mixed, and twice with an Eck sample mill (Fuji Paudal Co., Ltd. hammer mill) under the conditions of a screen diameter of 1 mm and a supply rate of 6 kg / hr. Crushed.
95.8 parts of the crushed product was charged into a Nauta mixer (conical mixer manufactured by Hosokawa Micron Co., Ltd.) and, while mixing, 2.5 parts of Toxanone GR31A (dispersing agent of Sanyo Kasei Co., Ltd., 40% aqueous solution of active ingredient), Neocall SWCE
(Daiichi Kogyo Seiyaku Co., Ltd. Wetting agent) 0.20 parts, water 12.
5 parts of the mixed solution was added and kneaded. The kneaded product was extruded and granulated from a screen having an opening diameter of 0.8 mm using an Eck-Peretta-EX-1 type (extrusion granulator manufactured by Fuji Paudal Co., Ltd.). After drying at 60 ° C. using a blower shelf dryer, sizing was performed using a sieve having an opening diameter of 1.000 mm and 0.500 mm to obtain 1.5% of compound (I) -1 and compound (B). Granules containing 5% each were obtained.

[0050]

EFFECT OF THE INVENTION When compound (I) and compound (A) or compound (B) are mixed and applied to a paddy field, the herbicidal range is expanded beyond the range of application obtained with each single agent. The width of weeding extends to grasses, Cyperaceae, general broad-leaved weeds, and general perennial weeds such as firefly, Cyperus cylindrica and Urikawa. In addition, the suitable application period can be expanded without compromising the safety of paddy rice. In addition, the herbicidal composition exhibits a synergistic effect on its herbicidal effect, and its effect is sufficiently exhibited when a mixture of doses much lower than the single-agent dose is used, and the herbicidal composition is sufficiently killed as a single treatment agent. The herb potency is increased, and its persistence is long-term. In addition, there is no chemical damage to paddy rice, and treatment before and immediately after transplantation is possible,
Soil treatment gives high effect.

Next, test examples will be described to more specifically show the effects of the present invention.

[0052]

[Test Example] Paddy soil was filled with water of 1 / 5000a Wagner pot filled with 3 kg each to make a paddy field, and seeds of broad-leaved weeds such as Taenia japonicus, firefly, eel, azalea, and yellow cypress were sown in this pot, and tubers of Spodoptera litura Planted. Furthermore, rice seedlings at the 2.5 leaf stage were transplanted and 2 pots were used.
The plants are grown in a greenhouse at 3 to 30 ° C, and on the 9th day after sowing, the prescribed amount of the drug is formulated in a wettable powder at the time of 1.5 leaf stage of the fly, diluted with water, and treated with 10 cc per pot. did. After that, it was grown in a greenhouse and the herbicidal effect was investigated 25 days after the chemical treatment. The results are shown in Table 2. In the table, EO indicates Tainubie, BL indicates broad-leaved weeds, SJ indicates firefly, CS indicates Mizugaya, SP indicates Urikawa, and OS indicates paddy rice.

The herbicidal effect was represented by the numbers 0 to 10 as follows depending on the weed control rate.

Suppression rate 0: 0 to 9% 1: 10 to 19% 2: 20 to 29% 3: 30 to 39% 4: 40 to 49% 5: 50 to 59% 6: 60 to 69% 7: 70-79% 8: 80-89% 9: 90-99% 10: 100% (complete death)

[0055]

[Table 2] ──────────────────────────────────── Compound number, application rate (g / a) EO BL SJ CS SP OS ──────────────────────────────────── (I) -1, 0.5 + (A), 10.0 10 10 10 8 8 0 (I) -1, 0.25 + (A), 10.0 10 10 10 8 7 0 (I) -1, 0.5 + (B), 10.0 10 10 10 8 6 0 ( I) -1, 0.25 + (B), 10.0 10 10 10 8 6 0 (I) -3, 1.0 + (A), 10.0 10 10 10 8 8 0 (I) -3, 0.5 + (A), 10.0 10 10 10 7 6 0 (I) -3, 1.0 + (B), 10.0 10 10 10 8 6 0 (I) -3, 0.5 + (B), 10.0 10 10 10 10 7 6 0 (I) -4, 1.0 + (A), 10.0 10 10 10 8 7 0 (I) -4, 0.5 + (A), 10.0 10 10 10 8 7 0 (I) -4, 1.0 + (B), 10.0 10 10 10 10 7 6 0 (I) -4, 0.5 + (B), 10.0 10 10 10 7 6 0 (I) -1, 0.5 6 9 3 2 4 0 (I) -1, 0.25 4 7 1 1 2 0 (I) -3, 1.0 6 9 5 3 3 0 (I) -3, 0.5 4 7 2 1 2 0 (I) -4, 1.0 5 9 3 2 4 0 (I) -4, 0.5 4 8 1 1 2 0 (A), 10.0 4 3 7 5 4 0 (B), 10.0 3 2 6 4 1 0 ────────────────────────────────────

Front Page Continuation (72) Inventor Toyokuni Honma 1041 Yasu, Yasu-cho, Yasu-gun, Shiga Sankyo Stock Company In-house

Claims (1)

[Claims] 1. A compound represented by the general formula (I): (In the formula, R is a C ₃ -C ₄ alkynyl group, tetrahydropyran-3 which may be substituted with 1 or 2 methyl groups.
-Yl group or tetrahydrofuran-3-yl group) and (R, S) -2-bromo-N- (α, α-dimethylbenzyl) -3,3-dimethylbutyramide or 1- ( 2-chlorobenzyl) -3
A paddy field herbicide composition containing-(α, α-dimethylbenzyl) urea.