JPS5931481B2 - Cyclohexanedione herbicide composition - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a herbicidal composition containing a mixture of a cyclohexane-1,3-dione compound and a known herbicide as an active ingredient. (In the formula, R1 is a hydrogen atom, an alkyl group, or a phenyl group, and R2 is an alkyl group, a linear or branched lower alkenyl group, a lower alkynyl group, a lower alkoxy lower alkyl group, a lower alkylthiomethyl group, a lower alkoxycarbonyl lower alkyl group) group or benzyl group, X is the same or different alkyl group substituted with the hydrogen atom of the cyclohexane ring, lower alkoxycarbonyl group, halogen atom,
A cyan group, a phenyl group, a phenyl group substituted with a halogen atom or a methoxy group, a styryl group, a furyl group, a chenyl group, a 5,5-pentamethylene group, or a 4,5-tetramethylene group, and n is O or Indicates an integer from 1 to 6.

), hydrates thereof, or metal salts thereof, and one or more selected from the group consisting of urea-based herbicides, triazine-based herbicides, carbamate-based herbicides, diphenyl ether-based herbicides, and phenoxyacetic acid-based herbicides. , acid amide herbicide, diazine herbicide, fatty acid herbicide or 3
-isopropyl-2,1,3-benzothiadiazine-4
This is a herbicidal composition characterized by containing as an active ingredient one or a mixture of two or more selected from -one-2,2-dioxide (hereinafter abbreviated as pentacine).

The present inventors have published Japanese Patent Application Publication No. 51-3755, 51-13749.
, 51-13750, 51-13756, 51-137
59, 51-131856, general formula CI)
By increasing the herbicidal power of the compound represented by
As a result of our research aimed at providing an economical and safe herbicide composition with no risk of chemical damage to crops, we discovered that the compounds represented by formula [I] include urea-based herbicides conventionally used; Triazine herbicides, carbamate herbicides, diphenyl ether herbicides, phenoxyacetic acid herbicides, acid amide herbicides, diazine herbicides,
When one or more herbicides selected from fatty acid herbicides or pentacine are blended, the selective herbicidal activity of the compounds represented by formula CI) and the various herbicides described above can be simply eliminated. The present invention was completed based on the discovery that the herbicidal effect not only increases additively but also has a synergistic herbicidal effect.

That is, a mixed herbicide composition of the compound represented by formula CI, I and the various herbicides described above can reduce the amount of the chemical used compared to the case of using each chemical alone, and has a complete and safe herbicidal effect in controlling weeds. and large economic effects.

For example, the urea herbicides used in the present invention include those shown below.

N-(3-,II>col-4-methoxy-phenyl)
-N'.N dimethylurea (generic name Metoxuron; trade name Dosanexx, hereinafter abbreviated as Dosanexx).

); N-(3,4-dichlorophenyl)-N', N'
-Dimethylurea (generic name: DCMU; trade name: Carmex; hereinafter abbreviated as Carmex).

): N-(3,4-dichlorophenyl)-N'-methoxy-N'-methylurea (hereinafter abbreviated as linuron); ■3-dimethyl-3-benzothiazol-2-ylurea (hereinafter referred to as tripnyl 1,3-dimethyl-3-(5-methylbenzothiazol-2-yl)urea (hereinafter abbreviated as A); 1°3-dimethyl-3-(5-t-butylbenzothiazole- 2-yl) urea (hereinafter abbreviated as B); ■・1,3-trimethyl-3-(5-methylbenzothiazol-2-yl)urea (hereinafter abbreviated as C); 1,1,3-trimethyl -3-(5-ethylbenzothiazol-2-yl)urea (abbreviated as below); Abbreviate.

); 1,1,3-trimethyl-3-(5,7-dimethylbenzothiazol-2-yl)urea (hereinafter abbreviated as F);

); These urea-based herbicides such as Dosanex, Carmex, and Linuron are used for field crops such as wheat, soybeans, potatoes, and ginseng, and are herbicides that exhibit particularly strong herbicidal power against common broad-leaved weeds.

However, it has the disadvantage that it is less effective against weeds of the true family, and there is a risk of chemical damage when treating stems and leaves.

However, the compounds represented by formula [■] have 1. When the above-mentioned urea-based herbicides are blended, the mixed herbicide composition can sufficiently kill target weeds at a much lower dose than when the compounds represented by formula CI) and urea-based herbicides are used alone. Furthermore, the chemical damage to crops is extremely slight.

Regarding the mixing ratio of each compound, the amount of the compounds represented by formula [■] is 1/10 to 20 times, preferably 1/4 to 10 times, more preferably 1/2 to 2 times the amount of the urea herbicide.
By adding twice the amount, a sufficient herbicidal effect can be achieved with a low dose.

In other words, when using only urea-based herbicides, 50 per 10 ares.
According to the present invention, compounds of formula CI) should be used in amounts of 1/4 to 200 g relative to urea herbicides.
When blended in 10 times the amount, urea herbicides with a 10A ratio of 12.5f to 1001 are generally sufficient, and are also extremely effective against weeds of the weed family, which are difficult to kill with urea herbicides alone.

Further, the triazine herbicides used in the present invention include those shown below.

2-chloro-4,6-ethylaminote 3,5-triazine (hereinafter abbreviated as simazine).

): 2-chloro-4-ethylamino-6-ituprobyl amino 3,5-triazine (hereinafter abbreviated as atrazine).

); 2-chloro-4,6-diitupropylaminenote 3
・5-triazine (hereinafter abbreviated as propazine).

); 2-methylmecarbuto 4-ethylamino-6-improvyl aminot 3,5-triazine (hereinafter abbreviated as ametrine);

); 2-methylmercapto-4,6-diitupropylamino-1,3,5-triazine (hereinafter abbreviated as promethrin).

); Triazine herbicides are herbicides mainly used in rice fields, wheat fields, corn fields, and carrot fields, and are herbicides that exhibit particularly strong herbicidal power against common broad-leaved weeds.

However, they have the disadvantage that they are less effective against weeds of the genus family, and that they often cause chemical damage and damage crops when sprayed on foliage.

However, when a triazine herbicide is blended with the compounds represented by formula [I], the mixed herbicide composition contains compounds represented by formula [CI] and [. The target weeds can be eradicated at a sufficient dose, and as a result, chemical damage to crops can be greatly reduced.

Regarding the mixing ratio of each herbicide, the compound represented by formula [I] is 1/10 that of the triazine herbicide.
A sufficient herbicidal effect can be achieved with a low dose by adding up to 20 times the amount, preferably 1/4 to 10 times, more preferably 1/2 to 2 times the amount.

In other words, when a triazine herbicide is used alone, it is necessary to use about 50 to 2,001 per 10 ares, but according to the present invention, the compound of formula (I) is used in an amount of 1/4 to 1/4 of the triazine herbicide. When blended in 10 times the amount, an extremely low dose is sufficient, and it is also extremely effective against weeds of the Physaceae family, which cannot be sufficiently killed with triazine herbicides alone.

Carbamate herbicides used in the present invention include those shown below.

3-Methoxycarbonylaminophenyl-N-(3'-
Methyl-phenyl)-carbamate (hereinafter abbreviated as fuemmedifam).

); Methyl N-(3,4-dichlorophenyl)-carbamate (generic name: MCC agent, trade name: SWEP, hereinafter abbreviated as SWETSUBU);

); Ingropyr N-(3-chlorphenyl)-carbamate (=generic name: chlorpropham, trade name: chloro-IPC, hereinafter abbreviated as chloro-IPC).

); 5-(4-chlorobenzyl)-N-N-diethylthiol carbamate (generic name: bentiocarp agent, trade name: Saturn, hereinafter abbreviated as Saturn).

); 4-chloro-2-butynyl N-(m-chlorophenyl) carbamate (common name, Calpain brand name, abbreviated as Calpain hereinafter.

); Methyl N-(4-aminobenzenesulfonyl)
Carbamate (generic name, Ashram, product name, Ajiran), hereinafter abbreviated as Ajilan.

); Carbamate herbicides are widely used in field crops, paddy fields, etc.
Moreover, although they are used as soil treatment agents and foliage treatment agents, many of them are less effective against grass weeds than broad-leaved weeds.

However, when a carbamate herbicide is added to the compounds represented by the formula [■], the range of grass species that can be killed is expanded compared to when the compounds represented by the formula CI) and the carbamate herbicide are used alone. Not only does it have a sufficient herbicidal effect at low doses, but it also greatly reduces chemical damage to crops.

Regarding the respective mixing ratios, the compound represented by formula CI, 1 is in an amount of 1/10 to 20 times the amount of the carbamate herbicide,
Preferably 1/4 to 10 times the amount, more preferably 1/2
By adding ~5 times the amount, a sufficient herbicidal effect can be achieved with a low dose.

Further, diphenyl ether herbicides used in the present invention include those shown below.

4'~nitro-2,4-dichloro-diphenyl ether (Hereinafter abbreviated as nip.

); 2,4-dichloro-3'-methoxy-4'-nitrodiphenyl ether (hereinafter abbreviated as X-52);

): 2,4,6-dolychlor-4'-nitrodiphenyl ether (hereinafter abbreviated as MO).

) Nidiphenyl ether herbicides are herbicides that are widely used for paddy rice and field cultivation, but their use is almost exclusively limited to soil treatment, and they have the disadvantage of causing phytotoxicity if applied to the leaves and foliage of crops.

When a diphenyl ether herbicide is blended with the compounds represented by formula CI), target weeds can be sufficiently killed with a lower dose than when each is used alone, and therefore, chemical damage to crops is reduced.

Regarding the respective mixing ratios, the compounds represented by formula CI) are 1/10 to 2 times the amount of diphenyl ether herbicides.
By adding 0 times the amount, preferably 115 to 5 times the amount, a sufficient herbicidal effect can be achieved with a low dose.

Furthermore, the phenoxyacetic acid herbicides used in the present invention include those shown below.

2-methyl-4-chloro-phenoxyacetic acid (MCP)
It will be abbreviated as A.

); 2,4-dichloro-phenoxyacetic acid (Hereinafter abbreviated as 2.4-D.

); Phenoxyacetic acid herbicides are herbicides that are used as foliage treatments for paddy rice or field cultivation, and have a particularly strong herbicidal power against general broad-leaved weeds, but have the disadvantage that they are less effective against regular weeds. .

However, when a phenoxyacetic acid herbicide is blended with the compounds represented by the formula [I], the resulting mixed herbicide composition is much more effective than when the compounds represented by the formula [■] and the phenoxyacetic acid herbicide are used alone. Target weeds can be sufficiently killed with low doses.

Regarding the mixing ratio of each herbicide, the compounds represented by formula CI) are mixed at a ratio of 1/1 to that of the phenoxyacetic acid herbicide.
By adding 10 to 20 times the amount, preferably 1/4 to 10 times the amount, and more preferably 1/2 to 2 times the amount, a sufficient herbicidal effect can be achieved with a low dose.

Furthermore, the acid amide herbicides used in the present invention include those shown below.

3,4-dichloroglopionanilide (generic name provanil Product name: Stam F-34, Hereinafter, it will be abbreviated as Stam.

); 5-chloro-4-mef-2-propionamidothiazole (trade name Select, hereinafter abbreviated as Select);

); Acid amide herbicides are herbicides that are widely used for water, upland rice, and field crops, but they have the disadvantage of being less effective against weeds of the family Pelidae.

However, when an acid amide herbicide is blended with the compounds represented by the formula [■], the resulting mixed herbicide composition has an extremely low drug content compared to the case where the compound represented by the formula CI) and the acid amide herbicide are used alone. The amount is sufficient to kill target weeds.

Regarding the mixing ratio of each herbicide, the compounds represented by formula CI) are 1/10 to 2 times the amount of acid amide herbicides.
By adding 0 times the amount, preferably 1/4 to 10 times the amount, and more preferably 1/3 to 2 times the amount, a sufficient herbicidal effect can be achieved with a low dose.

Further, fatty acid herbicides used in the present invention include those shown below.

Sodium 2,2-dichloropropionate (trade name Dowbon): Sodium 2,2,3,3-tetrafluoropropionate (common name Tetrapion, trade name Frenok, hereinafter abbreviated as Tetrapion).

); Fatty acid herbicides are herbicides mainly used in cultivated land, undergrowth, pastures, etc., and are particularly used to control silver grass, grass grass, etc., but their weeding effect is insufficient.

However, when a fatty acid herbicide is blended with the compounds represented by the formula CI], the mixed herbicide composition becomes a compound represented by the formula [
The target weeds can be sufficiently eradicated with a lower dose than when the compounds represented by [2] and fatty acid herbicides are used alone.

Regarding the mixing ratio of each herbicide, the compound represented by formula CI) has a ratio of 1/10 to 20 relative to the fatty acid herbicide.
By adding twice the amount, preferably 1/4 to 10 times, more preferably 1/3 to 2 times, a sufficient herbicidal effect can be achieved with a low dose.

In addition, the diazine herbicide used in the present invention includes:
There are the following.

1-phenyl-4-7 minnow 5-chloro-hyridazone (6) (generic name: Pyrazone, trade name: Pyramine, hereinafter abbreviated as Pyrazone).

); 3-cyclohexyl-5,6-drimethylene-uracil (generic name: renacil, hereinafter abbreviated as renacil).

); Diazine herbicides are soil treatment herbicides used in beet fields, etc., and are herbicides that exhibit strong herbicidal activity against general broad-leaved weeds.

However, it has the disadvantage that it is less effective against weeds of the true family, and there is a risk of phytotoxicity when spraying on leaves.

When the compounds represented by formula [I] are blended with this diazine herbicide, the selective herbicidal properties that the compounds represented by formula CI) and the diazine herbicide each have are simply expanded additively. It shows an extremely high synergistic herbicidal effect.

That is, the herbicidal composition according to the present invention has 1/2 of the compound represented by the formula [■] and the diazine herbicide.
The following low drug doses can sufficiently kill target weeds, and furthermore, chemical damage to crops can be greatly reduced.

To explain in more detail, the compounds represented by formula CI) are used in an amount of 1/10 to 10 times the amount of the diazine herbicide,
Preferably 1/4 to 5 times the amount, more preferably 1/2 to 5 times the amount
If added in equal amounts, a sufficient herbicidal effect can be achieved with a low dose of diazine herbicide.

That is, when using a diazine herbicide alone, it is necessary to use 300 to 5,001 parts per 10 ares, but according to the present invention, the amount of diazine herbicide used is based on the formula CI)
When compounding 1/4 to 5 times the amount of diazine herbicides, 100 to 300 grams per 10 ares is generally sufficient, and the diazine herbicide cannot be sufficiently killed by the sole use of diazine herbicides. It is also extremely effective against weeds.

Other herbicides used in the present invention include 3-isopropyl-2,1,3-benzo-IF-7 diazin-4-one-2,2-dioxide (generic name bentazone, hereinafter abbreviated as pentacin). .

); and so on.

Pentacine is a herbicide used in rice fields, soybean fields, etc., and exhibits strong herbicidal power against broad-leaved weeds.

However, it has the disadvantage that it is significantly less effective against weeds of the true family, and is also associated with the risk of chemical damage.

When compounds represented by formula CI) are blended with this pentacine, the selective herbicidal properties of the compound of formula CI) and pentacine, respectively, are not only increased additively, but also an extremely high synergistic killing effect is achieved. Has grass effect.

That is, the herbicidal composition according to the present invention sufficiently kills target weeds at a much lower dose than when the compound represented by formula CI) and pentacine are used alone, and furthermore, the chemical damage to crops is greatly reduced. .

To explain in more detail, the compound represented by the formula [■] is used in an amount of 1/10 to 5 times, preferably 1/10 to 5 times the amount of pentacine.
By adding 1/4 to 2 times the amount, more preferably 1/2 to the same amount, a sufficient herbicidal effect can be achieved with a low dose.

In other words, when using pentacine alone, it is 50 to 30 per 10 ares.
However, according to the present invention, the amount of pentacine used is generally 50 to 2,001 g per 10 ares when compound of formula [■] is blended in 1/4 to 2 times the amount.
is sufficient, and it is also effective against weeds of the family Tractaceae, which are difficult to kill with pentacine alone.

The characteristics of each of the known herbicides, the compounds represented by the general formula [I], and the mixed herbicide composition have been described above.Of course, two or more of the above-mentioned known herbicides and the compounds represented by the general formula [■]
A mixed herbicidal composition with these compounds exhibits a synergistic effect when mixed with one type of herbicide, and can be an excellent herbicidal composition that can be applied in all cases.

The compound represented by the general formula [I] can have the following tautomeric structural formula.

One of the active ingredients of the herbicide of the present invention, a compound represented by general formula CI], is synthesized, for example, as follows.

(In the formula, R1, R2, X and n have the same meanings as defined above.

) Among the compounds represented by the general formula [■], compounds having excellent synergistic effects with the general formula (1B, [■], and [■]), in which R1 represents a lower alkyl group, are , R2 represents a lower alkyl group, a lower alkenyl group or a lower alkynyl group, and R3 represents a lower alkyl group.

) The raw material compound of the general formula (n) is synthesized, for example, as follows.

The metal salt of the compound represented by the general formula [■] is obtained by reacting the compound represented by the general formula [I] with a caustic alkali in the case of an alkali metal salt, and the other metal salt is a caustic alkali metal salt of It can be obtained by reacting with various metal salts.

Further, a hydrate of the compound represented by the general formula [■] can be obtained by reacting the compound represented by the general formula [■] with water.

Representative examples of compounds represented by the general formula CI) used in the present invention are shown in Table 1.

The herbicidal composition of the present invention contains an appropriate amount of one or more selected from the compound represented by the general formula (I), a metal salt thereof, or a hydrate thereof, and a urea herbicide or a triazine herbicide. herbicides, carbamate herbicides, diphenyl ether herbicides, phenoxyacetic acid herbicides, acid amide herbicides,
Appropriate amounts of one or more selected from diazine herbicides, fatty acid herbicides, or pentacin are generally mixed with a carrier in the form of agrochemicals commonly used, such as wettable powders, emulsions, and powders. , used in the form of granules, etc.

Examples of solid carriers include talc, bentonite, clay, and diatomaceous materials, and examples of liquid carriers include water, alcohol, benzene, xylene, kerosene, mineral oil, cyclohexene, dimethylformamide, and the like.

If necessary, a surfactant may be added to these preparations in order to obtain a uniform and stable form.

In the herbicidal composition of the present invention, the concentration of the organic component can be varied depending on the form of the formulation described above, but for example, in the case of a wettable powder, it is 5 to 80%, preferably 10 to 60%.
%, in emulsions 5-70%, preferably 20-60%
, 0.5 to 30% for powders and granules, preferably 1 to 30%
A concentration of 10% is used.

The wettable powders and emulsions obtained in this way are diluted with water to a predetermined concentration to form a suspension or emulsion, and the powders and granules are sprayed or mixed-phase treated on the soil before weed germination. Or, after weed germination, foliar spray treatment is applied.

When actually applying the herbicide composition of the present invention, 1.
101 or more active ingredients per 0 are, preferably 251
The above appropriate amount is applied.

Next, some examples regarding the herbicide composition of the present invention are shown,
The active ingredient compounds, additives, and addition ratios are not limited to those in this example, but can be varied within a wide range.

Example 1 Emulsion compound 50 20 parts Lysuron 20 parts Xylene
35 parts dimethylformamide
15 parts phosphoryoxyethylene phenyl ether Mix and dissolve 10 parts or more to obtain 40% active ingredient
An emulsion was obtained.

Example 2 Emulsion compound 50 20 parts Carmex 20 parts Xylene
35 parts dimethylformamide
15 parts phosphoryoxyethylene phenyl ether Mix and dissolve 10 parts or more to obtain 40% active ingredient
An emulsion was obtained.

Example 3 Emulsion Compound 32 20 parts Carmethox 20 parts Xylene
35 parts dimethylformamide 15 parts holoxyethylene phenyl ether 10 parts or more are mixed and dissolved to obtain 40 parts of the active ingredient.
% emulsion was obtained.

Example 4 Emulsion Compound 83 20 parts Carmex 20 parts Xylene
35 parts dimethylformamide 15 parts holoxyethylene phenyl ether 10 parts or more are mixed and dissolved to obtain 40 parts of the active ingredient.
% emulsion was obtained.

Example 5 Granule Compound 50 3 parts Dosanesox 4 parts Talc
35 part clay
35 parts bentonite
16 parts alkyl sulfate soda
After uniformly mixing 7 parts or more and pulverizing it finely, it is made into granules with a diameter of 0.5 to 1.0 mm using a granulator to give 7% of the active ingredient.
granules were obtained.

Example 6 Wettable powder compound 50 20 parts 1.3-
Dimethyl-3-(5-methylbenzothiazol-2-yl) 20 parts urea resin ± 23 parts talc
29 parts Sodium alkyl sulfate 8 parts or more were uniformly mixed and finely ground to obtain a wettable powder containing 40% of the active ingredient.

Example 7 Emulsion compound 50 20 parts 1.3-
Dimethyl-3-(5-t-buty 20 parts Rubensothiazol-2-yl) urea xylene 35 parts Dimethylformamide 15 parts Porioxyethylene phenyl ether At least 10 parts were mixed and dissolved to obtain an emulsion containing 40% of the active ingredient. .

Example 8 Emulsion compound 50 20 parts 1.3-
Dimethyl-3-(5,7-dime 20 parts thylbenzothiazol-2-yl) urea (E) Xylene 35 parts Dimethylformamide 15 parts Polyoxyethylene phenyl ether 10 parts or more are mixed and dissolved uniformly to obtain 40% active ingredient. An emulsion was obtained.

Example 9 Emulsion compound 32 20 parts E
20 parts xylene
35 parts dimethylformamide
15 parts polyoxyethylene phenyl ether At least 10 parts were mixed and dissolved to obtain an emulsion containing 40% of the active ingredient.

Example 10 Emulsion compound 83 20 parts E
20 parts xylene
35 parts dimethylformamide
15 parts polyoxyethylene phenyl ether At least 10 parts were mixed and dissolved to obtain an emulsion containing 40% of the active ingredient.

Example 11 Emulsion compound 50 15 parts 1.1.
3-Trimethyl-3-(5.730 parts-dimethylbenzothiazol-2-yl)urea xylene 35 parts dimethylformamide 10 parts polyoxyethylene phenyl ether 10 parts or more were mixed and dissolved to obtain an emulsion containing 45% of the active ingredient. Ta.

Example 12 Wettable powder compound 50 15 parts Tribnyl 30 parts
23 parts talc
24 parts alkyl sulfate soda
At least 8 parts were mixed uniformly and finely ground to obtain a wettable powder containing 45% of the active ingredient.

Example 13 Emulsion compound 50 25 parts Promethrin 25 parts Xylene
30 parts dimethylformamide
10 parts polyoxyethylene phenyl ether Mix and dissolve 10 parts or more to obtain 50% active ingredient
An emulsion was obtained.

Example 14 Emulsion compound 83 20 parts promethrin 20 parts dimethylformamide 15 parts polyethylene phenyl ether 10 parts xylene
40% active ingredient by mixing and dissolving 35 parts or more
An emulsion was obtained.

Example 15 Emulsion compound 32 20 parts promethrin 20 parts xylene
35 parts dimethylformamide
15 parts polyethylene phenyl ether Mix and dissolve 10 parts or more to make 40% active ingredient
An emulsion was obtained.

Example 16 Emulsion compound 50 30 parts Simazine
10 parts xylene
35 parts dimethylformamide 15 parts phosphoryoxyethylene phenyl ether 7/L/IQ parts or more are mixed and dissolved to obtain 40 parts of active ingredient.
% emulsion was obtained.

Example 17 Wettable powder compound 50 30 parts Propazine 15 parts Diatomaceous earth
, tritone total
24 parts or more of 8 parts or more of sodium alkyl sulfate were uniformly mixed and finely ground to obtain an aqueous phase agent containing 45% of the active ingredient.

Example 18 Water phase agent compound 50 30 parts Simetrine 15 parts Diatomaceous earth
23 sounds μ″′ri
24 parts or more of 8 parts or more of sodium alkyl sulfate were uniformly mixed and finely ground to obtain an aqueous phase agent containing 45% of the active ingredient.

Example 19 Granule Compound 50 5 parts Simazine
3 part talc
35 part clay
35 parts bentonite
15 parts alkyl sulfate soda
After uniformly mixing 7 parts or more and pulverizing it finely, it is made into granules with a diameter of 0.5 to 1 mm using a granulator, and the active ingredient is 8%.
granules were obtained.

Example 20 Emulsion compound 50 20 parts; Fuemmedifam 20 parts xylene
35 parts dimethylformamide 15 parts pholyoxyethylene phenyl ether 10 parts The above ingredients were mixed and dissolved to obtain an emulsion containing 40% of the active ingredient.

Example 21 Emulsion Compound 32 10 parts Fuemmedifam 10 parts Xylene
35 parts dimethylformamide 35 parts-polyoxyethylene phenyl ether 10 parts or more are mixed and dissolved to obtain active ingredient 2.
A 0% emulsion was obtained.

Example 22 Emulsion' Compound 50 20 parts calpain 20 parts xylene
35 parts dimethylformamide 15 parts holoxyethylene phenyl ether 10 parts or more are mixed and dissolved to obtain active ingredient 4.
A 0% emulsion was obtained.

Example 23 Emulsion compound 51 20 parts calpain 20 parts xylene
35 parts dimethylformamide 15 parts polyoxyethylene phenyl ether 10 parts or more are mixed and dissolved to obtain 40 parts of the active ingredient.
% emulsion was obtained.

Example 24 Emulsion compound 50 15 parts Arzira 7 25 parts xylene
35 parts dimethylformamide
15 parts polyoxyethylene phenyl ether At least 10 parts were mixed and dissolved to obtain an emulsion containing 40% of the active ingredient.

Example 25 Wettable powder compound 50 10 parts sweep
40 parts Keisou ±
20 parts talc
20 parts alkyl sulfate soda
At least 10 parts were mixed uniformly and finely ground to obtain a wettable powder containing 50% of the active ingredient.

Example 26 Granule compound 50 2 parts chloro-
IPC 4 parts Talc 35 parts Clay 35 parts Bentonite 16 parts Sodium alkyl sulfate 8 parts or more are mixed uniformly, pulverized finely, and made into granules with a diameter of 0.5 to 10 mm using a granulator to form granules containing 6% of the active ingredient. Obtained.

Example 27 Granule compound 50 2 parts turn
6 part talc
35 part clay
35 parts bentonite
15 parts alkyl sulfate soda
After uniformly mixing 7 parts or more and pulverizing it finely, it is made into granules with a diameter of 0.5 to LOmm using a granulator, and the active ingredient is 8%.
granules were obtained.

Example 28 Water phase agent compound 50 10 parts nip
30 part Keisou ±
28 parts talc
24 parts alkyl sulfate soda
At least 8 parts were mixed uniformly and finely ground to obtain a wettable powder containing 40% of the active ingredient.

Example 29 Emulsion compound 50 10 parts nip
30 parts xylene
35 parts dimethylformamide
15 parts polyoxyethylene phenyl ether At least 10 parts were mixed and dissolved to obtain an emulsion containing 40% of the active ingredient.

Example 30 Emulsion Compound 32 10 parts nip
30 parts xylene
35 parts dimethylformamide
15 parts polyoxyethylene phenyl ether At least 10 parts were mixed and dissolved to obtain an emulsion containing 40% of the active ingredient.

Example 31 Emulsion compound 50 10 parts X52
30 parts xylene 35 parts dimethylformamide 15 parts polyoxyethylene phenyl ether At least 10 parts were mixed and dissolved to obtain an emulsion containing 40% of the active ingredient.

Example 32 Emulsion compound 15 10 parts X-52
30 parts xylene 35 parts dimethylformamide 15 parts polyoxene ethylene phenyl ether At least 10 parts were mixed and dissolved to obtain an emulsion containing 40% of the active ingredient.

Example 33 Emulsion compound 58 10 parts X-52
30 parts xylene 35 parts dimethylformamide 15 parts polyoxyethylene phenyl ether At least 10 parts were mixed and dissolved to obtain an emulsion containing 40% of the active ingredient.

Example 34 Granule compound 50 3 parts X-52
6 parts talc 35 parts clay 35 parts bentonite 15 parts alkyl sulfate sodium 6 parts or more are mixed uniformly, pulverized finely, and made into granules with a diameter of 0.5 to 1.0 mm using a granulator, containing 9% of the active ingredient. Granules were obtained.

Example 35 Wettable powder compound 50 20 parts 2.4-
I) 20 parts diatomaceous earth 25 parts Merck
25 parts and 10 parts or more of sodium alkyl sulfate were uniformly mixed and finely ground to obtain a wettable powder containing 40% of the active ingredient.

Example 36 Emulsion compound 59 20 parts 2.4-
D20 parts xylene 35 parts dimethylformamide 15 parts polyoxyethylene phenyl ether 10 parts or more were mixed and dissolved to obtain an emulsion containing 40% of the active ingredient.

Example 37 Emulsion Compound 50 10 parts stam
30 parts xylene
35 parts dimethylformamide
15 parts polyoxyethylene phenyl ether At least 10 parts were mixed and dissolved to obtain an emulsion containing 40% of the active ingredient.

Example 38 Wettable powder compound 50 15 parts stam
30 parts diatomaceous earth
23 parts talc
22 parts alkyl sulfate soda
At least 10 parts were uniformly mixed and finely ground to obtain an aqueous phase agent containing 45% of the active ingredient.

Example 39 Granule compound 50 3 parts selection
5 parts talc
35 part clay
35 parts bentonite
15 parts alkyl sulfate soda
After uniformly mixing 7 parts or more and pulverizing it finely, it is made into granules with a diameter of 0.5 to 10 mm using a granulator to obtain the active ingredient 8.
% granules were obtained.

Example 40 Emulsion compound 50 10 parts selection
30 parts xylene
35 parts dimethylformamide
15 parts polyoxyethylene phenyl ether Mix and dissolve 10 parts or more to make 40% active ingredient
An emulsion was obtained.

Example 41 Emulsion compound 61 10 parts selection
30 parts xylene
35 parts dimethylformamide 15 parts polyoxyethylene phenyl ether 10 parts or more are mixed and dissolved to obtain 40 parts of the active ingredient.
% emulsion was obtained.

Example 42 Emulsion compound 51 10 parts selection
30 parts xylene
35 parts dimethylformamide 15 parts polyoxyethylene phenyl ether 10 parts or more are mixed and dissolved to obtain 40 parts of the active ingredient.
% emulsion was obtained.

Example 43 Emulsion compound 50 10 parts tetrapion 30 parts xylene
35 parts dimethylformamide
15 parts polyoxyethylene phenyl ether Mix and dissolve 10 parts or more to make 40% active ingredient
An emulsion was obtained.

Example 44 Emulsion compound 83 10 parts tetrapion 30 parts xylene
35 parts dimethylformamide
15 parts polyoxyethylene phenyl ether Mix and dissolve 10 parts or more to make 40% active ingredient
An emulsion was obtained.

Example 45 Emulsion compound 32 10 parts tetrapion 30 parts xylene
35 parts dimethylformamide
15 parts polyoxyethylene phenyl ether Mix and dissolve 10 parts or more to make 40% active ingredient
An emulsion was obtained.

Example 46 Emulsion compound 50 10 parts Pyrazone
30 parts xylene
35 parts dimethylformamide
15 parts polyoxyethylene phenyl ether Mix and dissolve 10 parts or more to make 40% active ingredient
An emulsion was obtained.

Example 47 Emulsion Compound 83 10 parts Pyrazone
30 parts xylene
35 parts dimethylformamide 15 parts polyoxyethylene phenyl ether 10 parts or more are mixed and dissolved to obtain 40 parts of the active ingredient.
% emulsion was obtained.

Example 48 Emulsion Compound 51 10 parts Pyrazone
30 parts xylene
35 parts dimethylformamide
15 parts polyoxyethylene phenyl ether Mix and dissolve 10 parts or more to make 40% active ingredient
An emulsion was obtained.

Example 49 Wettable powder compound 50 15 parts Pyrazone
30 parts diatomaceous earth
.

3 parts talc 24
8 parts or more of sodium alkyl sulfate were uniformly mixed and finely ground to obtain a wettable powder containing 45% of the active ingredient.

Example 50 Granule Compound 50 3 parts Pyrazone
4 parts talc
35 part clay
35 parts bentonite
16 parts alkyl sulfate soda
After uniformly mixing 7 parts or more and pulverizing it finely,
The mixture was made into granules with a diameter of 0.5 to 1.0 mm using a granulator to obtain granules containing 7% of the active ingredient.

Example 51 Emulsion Compound 50 20 parts Renacil
20 parts xylene
A mixed emulsion containing 35 parts dimethylformamide, 15 parts polyoxyethylene phenyl ether, and 10 parts or more was dissolved to obtain an emulsion containing 40% of the active ingredient.

Example 52 Emulsion Compound 83 20 parts Renacil
20 parts xylene
35 parts dimethylformamide
15 parts polyoxyethylene phenyl ether Mix and dissolve 10 parts or more to make 40% active ingredient
An emulsion was obtained.

Example 53 Wettable powder compound 50 15 parts Renacil 30 parts Diatomysium ±
23 parts talc
24 parts alkyl sulfate soda
At least 8 parts were mixed uniformly and finely ground to obtain a wettable powder containing 45% of the active ingredient.

Example 54 Emulsion compound 50 20 parts pentacine 20 parts xylene
35 parts dimethylformamide 15 parts polyoxyethylene phenyl ether 10 parts or more are mixed and dissolved to obtain 40 parts of the active ingredient.
% emulsion was obtained.

Example 55 Emulsion compound 20 parts pentacine 20 parts xylene
35 parts dimethylformamide 15 parts polyoxyethylene phenyl ether 10 parts or more are mixed and dissolved to obtain 40 parts of the active ingredient.
% emulsion was obtained.

Example 56 Wettable powder compound 50 30 parts Bendazone 15 parts Diatomaceous earth
23 parts talc
24 parts and 8 parts or more of alkyl sodium sulfate were uniformly mixed and finely ground to obtain a wettable powder containing 45% of the active ingredient.

Example 57 Granule Compound 50 4 parts Pentasil 3 parts Talc
35 part clay
35 parts bentonite
16 parts alkyl sulfate
After uniformly mixing 7 parts or more and pulverizing it finely, use a granulator to make it into granules with a diameter of 0.5~loam to give 7% of the active ingredient.
granules were obtained.

Next, test examples regarding the effects of the herbicide composition of the present invention will be shown.

Test Example 1 Stem and Leaf Treatment Test Weed grass and pigweed were grown in 4-inch pots, and when each plant had 4 leaves, each drug solution of the treatment concentration prepared by diluting the test compound emulsion prepared according to Example 1 with water was applied to the weed stems and leaves. Sprayed with a player.

The survey was conducted after three weeks by measuring the weight of the above-ground parts of the weeds.
The results shown in the table were obtained.

Claims (1)

[Claims] 1 General formula (in the formula, R1 is an alkyl group, R2 is an alkyl group or a lower alkenyl group, and X is the same or different alkyl group or lower alkoxycarbonyl group substituted for the hydrogen atom of the cyclohexane ring) or a cyano group 5, and n is 0 or an integer from 1 to 3.), a hydrate thereof, or a metal salt thereof; Chlor-4-methoxy-phenyl)-N'
・N-dimethylurea, N-(3,4-dichloro-phenyl)-N', N'-dimethylurea, N-(3,4-dichloro-phenyl)-N'-methoxy-N'-methylurea, ■・3-dimethyl-3-benzothiazol-2-ylurea, 1,3-dimethyl-3-(5-methylbenzothiazol-2-yl)urea, 1,3-dimethyl-3-(5-t- butylbenzothiazol-2-yl)urea, 1,1,3-trimethyl-3-(5-methylbenzothiazol-2-yl)urea, ■1,3-trimethyl-3-(5-ethylbenzothiazole- 2-yl) urea, ■3-dimethyl-3-(5,7-dimethylpenzothiazol-2-yl) urea and 1,1,3-trimethyl-3-(5,7-dimethylbenzothiazole) -2-yl) urea-based herbicides selected from the group of ureas; 2-chloro-4,6-dinithylaminoto-3,5-triazine, 2-chloro-4-ethylamino-6-ituprovira; Minnow 1,3,5-triazine, 2-chloro-4,6-diituprobylamine 3,5
-triazine, 2-methylmercapto-4-ethylamino-6-ituprobylamino 3,5-triazine, and 2-methylmercapto-4,6-diituprobylamino 1,3.
Triazine herbicide selected from the group of 5-triazines: 3-methoxycarbonylaminophenyl-N-(3'-
) thyl-phenyl)-carbamate 1, I-thyl N-(3
・4-)Chlorphenyl)-carbamate, Impropyl N-(3-chlorophenyl)-carbamate, 5-(4-chlorobenzyl)-N'・N-diethylthiolcarbamate, 4-chloro-2-phF- Nyl N (m-chlorophenyl)
carbamate and methyl N-(4-aminobenzenesulfonyl)carbamate, a carbamate herbicide selected from the group of - a diphenyl ether herbicide selected from the group of nitrodiphenyl ether and 2,4,6-dolychloro-4'-nitrodiphenyl ether; selected from the group of 2-methyl-4-chloro-phenoxyacetic acid and 2,4-dichloro-phenoxyacetic acid. phenoxyacetic acid herbicide; acid amide herbicide selected from the group of 3,4-dichloropropionanilide and 5-chloro-4-methyl-2-propionamidothiazole; 1-phenyl-4-amine-5 -Chlor-pyridazone-(6) and 3-cyclohexyl-5,6-) A diazine herbicide selected from the group of IJ methylene-uracil; Sodium 2,2-dichloropropionate and 2,2-
A fatty acid herbicide selected from the group of sodium 3,3-tetrafluoropropionate or 3-isopropyl-2,1,3-benzothiadiazin-4-one-2.
A herbicidal composition comprising, as an active ingredient, one or a mixture of two or more 2-dioxides selected from 2-dioxide.