JPH04193803A - Herbicide composition - Google Patents

Abstract

PURPOSE:To obtain a herbicide composition enhanced in safety to crops without lowering herbicidal effect, containing aurea compound having strong herbicidal effect or by combining the urea compound and other herbicides with a specific amine compound. CONSTITUTION:The objective composition containing (A) a urea compound expressed by formula I [Ar is formula II to formula VI (R<1> to R<10> and R<21> to R<26> are H, alkyl or alkoxy), etc.; A is N or CX (X is H, Cl, NO2 or CF3); B is H, methyl or methoxy] or a composition consisting of the above-mentioned urea compound and other herbicides and (B) a compound expressed by formula VII [R<29> is alkyl, cycloalkylakyl, alicyclic hydrocarbon group, etc.; R<40> is H, alkyl, alkenyl, D-Y (D is 2-4C alkylene; Y is OH or NH2); R<41> is H, alkyl, hydroxyalkyl or aminoalkyl] as active ingredients.

Description

[Detailed description of the invention] [Industrial application field] The present invention relates to herbicidal compositions.

[Conventional technology]

Wheat, corn, rice, soybeans, etc. are important crops, and many herbicides have been used to increase the yield of these crops, but conventional herbicides have limited herbicidal activity and crop safety. However, there is a need for a safe herbicide that kills harmful weeds in small amounts and does not cause chemical damage to crops.

As such herbicides, the following general formula (I) [wherein A
r is a formula; atom,
Represents a lower alkyl group, lower alkoxy group or hydroxyl group, provided that R2 and R3, R6 and R7, R9 and R'', R
” and RI 5 or R1'' and R16 each represent an alkylene chain optionally substituted with a lower alkyl group, and form a 5- to 6-membered ring together with the carbon atom to which they are bonded. or R'' and R'2 may be connected to represent an ethylenedioxy group, or R'' and R'' may be connected to represent a dichloromethylene group). In JP-A-63-10779, a group of urea compounds represented by the group A represents a nitrogen atom, a substituent, or a trifluoromethyl group, and B represents a hydrogen atom, a methyl group, or a methoxy group are disclosed. A composition of urea compounds represented by the general formula (I) and other herbicides has been proposed in Japanese Patent Application No. 9501/1999.

On the other hand, in JP-A No. 53-94035, the following formula 8% [wherein L is -(CH2), - group (where m is 4 to 18
) , -(CH2)3NH(CH,2)4
- group, (CH2)4NH(CH2)4- group, (CHz)aNH(CH2)nNH(,CH2)a- group, fluorenylene group or naphthylene group] and acid addition salts thereof. It is described that it has a drug-damaging effect. However, the herbicide that is targeted by this phytotoxicity reducing effect has the following formula [wherein,
R42 and R43 are the same or different and represent a hydrogen atom, a halogen atom, a nitro group, a methylsulfonyl group, a trifluoromethyl group, an alkyl group having 1 to 3 carbon atoms, or an alkoxy group having 1 to 3 carbon atoms, and R44 is a hydrogen atom. , represents a carboxymethyl group or an alkyl group having 1 to 3 carbon atoms, and R45 is -CH2-1-CH(CH3)7, (CH
2) 2-1 (CH2)-- or -CH(i-C2H
It is limited only to N-substituted or N-unsubstituted phenylcarbamoyl amino acid derivatives, salts thereof, or esters thereof, represented by the general formula (
It does not contain any compound represented by I).

[Invention or problem to be solved]

The compound of general formula (I) or a composition of the compound of general formula (I) and other herbicides exhibits a very strong herbicidal effect, but on the other hand, there is some concern about chemical damage depending on the type of crop. In addition, selectivity between crops and weeds may be low.

Therefore, an object of the present invention is to selectively exert high herbicidal effects of such herbicides on weeds, thereby increasing safety for crops.

The present inventors have discovered that the problems of the present invention can be solved by combining a specific amine compound with the above type of herbicidal composition, and have completed the present invention.

[Means to solve the problem]

The herbicidal composition of the present invention has the general formula (I) [wherein, Ar is the formula; Represents a lower alkoxy group, R'' represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, or a hydroxyl group, provided that R2 and R3, R6 and R7, Rs and Rl'o, RII
ToRI6 Mata l;! R'stR'' (7) Both groups are linked to represent an alkylene chain optionally substituted with a lower alkyl group, and may form a 5- to 6-membered ring together with the carbon atom to which they are bonded, Alternatively, RII and R'' may be connected to each other to represent an ethylenedisoxy group, or R'4 and R'' may be connected to each other to represent a dichloromethylene group), and A is A urea compound represented by a nitrogen atom or -C= (where X represents a hydrogen atom, a chlorine atom, a nitro group, or a trifluoromethyl group), and B represents a hydrogen atom, a methyl group, or a methoxy group, or a general Compositions of urea compounds represented by formula (I) and other herbicides, as well as general formula (II) R3@R41)R41N
(I[) [wherein R'' is an alkyl group having 1 to 8 carbon atoms, a cycloalkylalkyl group having 4 to 8 carbon atoms which may be substituted with an aminoalkyl group, an alkenyl group having 3 to 6 carbon atoms, An alkynyl group having 3 to 5 carbon atoms, a non-aromatic cyclic hydrocarbon group having 3 to 9 carbon atoms which may be substituted with an amino group or an alkyl group, and a 7 to 12 carbon number which may be substituted with an alkoxy group. an aralkyl group or -C-X (wherein C is an optionally branched alkylene group having 2 to 8 carbon atoms and optionally substituted with a hydroxyl group, X is a hydroxyl group, and
~3 alkoxy group, amino group, alkylamino group having 1 to 4 carbon atoms, or aminoalkylamino group having 2 to 3 carbon atoms), R40 is a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, a carbon number 3-6 alkenyl group or -D-Y
(In the formula, D represents an optionally branched alkylene group having 2 to 4 carbon atoms, Y represents a hydroxyl group or an amino group), and R" and R" represent the number of members together with the nitrogen atom to which they are bonded. 3 to 8 rings may be formed, and this ring may contain an oxygen atom or a nitrogen atom, and may include an alkyl group, a hydroxyalkyl group, a benzyl group, an amino group, a formyl group, an alkoxycarbonyl group, or an aminoalkyl group. may have as a substituent, R'' represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, a hydroxyalkyl group having 2 to 3 carbon atoms, or an aminoalkyl group having 1 to 3 carbon atoms, and further R "9, R40 and R" may form a bridged ring having 4 to 12 members together with the nitrogen atom to which they are bonded, and this ring may contain a double bond or a nitrogen atom, and may be branched. It contains as an active ingredient at least one compound selected from the group of compounds represented by the following.

In the general formula (I), examples of the lower alkyl group represented by R1 to R'' include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a 5BC-butyl group, a tert-butyl group, an isobutyl group, and the like. Examples of the lower alkoxy group include methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, 5eC-butoxy group, and isobutoxy group.

Specific examples of the compound of general formula (I) include those listed in Tables 1 to 11.

(Margins below this page) Table 1 Table 1 (continued) Table 1 (continued) Table 1 (continued) Table 1 (continued) Table 1 (continued) Table 2 Table 2 (continued) Section 2 Table (continued) Table 2 (continued) Table 2 (continued) Table 2 (continued) Table 3 Table 3 (continued) Table 3 (continued) Table 5 Table 5 (continued) Table 6 Table 6 (Continued) Table 7 Table 8 Table 9 Table 10 Table 11 Other herbicides that can be used in combination with the urea compound represented by general formula (I) are not particularly limited or are listed as preferred examples. is described in Japanese Patent Application No. 2-9501 [a
] 4-chloro-2-methylphenoxyacetic acid, [b)2
- (4-chloro-2-methylphenoxy)propionic acid, [C3A-amino-3,5-dichloro-6-fluoro-2-pyridyloxyacetic acid, [:d) 3,4-dichloropropionic acid anilide, (e ) N-(3-chlorophenyl)carbamic acid isopropyl ester, (f)
N,N-diethylthiolcarbamic acid-8-(2-chlorobenzyl) ester1. (g) 2-methylthio-4
-isopropylamino-6-methylamino-1,3゜5
-triazine, [h] 2-chloro-4,6-bis(ethylamino)-1,3,5-) riazine, (i) 4
-amino-6-t-butyl-3-methylthio-1,2,
4-) riazin-5(4H)-one, [j]3-isopropyl-IH-2,1,3-hendithiazinone-4(
Mention may be made of 3H)-one-2,2-oxide.

In general formula (II), examples of the alkyl group of R3Q include methyl group, ethyl group, propyl group, isopropyl group, butyl group, 5ee-butyl group, tert-butyl group, isobutyl group, amyl group, and isoamyl group. I'll come. Examples of the cycloalkylalkyl group which may be substituted with an aminoalkyl group having 4 to 8 carbon atoms include a cyclopropylmethyl group, a cyclopentylmethyl group, a cyclohexylmethyl group, a 3-(aminomethyl)cyclohexylmethyl group, and a 4-(aminomethyl) group. ) cyclohexylmethyl group, etc. Examples of alkenyl groups include allyl group, 2-butenyl group, 3-butenyl group, ■-methyl-2-
Propenyl group, 2-methyl-2-propenyl group, ■, 2
-Dimethyl-2-propenyl group, 2-methyl-2-butenyl group, 3-methyl-2-butenyl group, 2,3-dimethyl-2-butenyl group, etc., and examples of the alkynyl group include 2-propynyl group. , 2-butynyl group, 3-
butynyl group, 1-methyl-2-propynyl group, 1,1
-dimethyl-2-propynyl group and the like. The alicyclic hydrocarbon group may be monocyclo or bicyclo, and may be further substituted with an amino group or an alkyl group. Examples of these include cyclopropyl group, cyclobutyl group, cyclopentyl group, ■-methylcyclopentyl group, 2-methylcyclopentyl group, 3-methylcyclopentyl group,
Methylcyclopentyl group, cyclohexyl group, 1-methylcyclohexyl group, 2-methylcyclohexyl group, 3
-Methylcyclohexyl group, 4-methylcyclohexyl group, 2-aminocyclohexyl, 3-aminocyclohexyl, 4-aminocyclohexyl group, cycloheptyl group, cyclooctyl group, 1-norbornyl group, 7-norbornyl group, etc. can. Examples of aralkyl groups optionally substituted with alkoxy groups include benzyl groups,
4-methoxybenzyl group, 3,4-dimethoxybenzyl group, α-methylbenzyl group, phenethyl group, 4-methoxyphenethyl group, 3,4-dimethoxyphenethyl group, 4
-phenylbutyl group, etc.

-C-X is 2-hydroxyethyl group, 2-hydroxypropyl group, 3-hydroxypropyl group, 2-methoxyethyl group, 2-ethoxyethyl group, 3-methoxypropyl group, 3-ethoxypropyl group, -aminoethyl group, 2-(methylamino)ethyl group, 2-(ethylamino)ethyl group, 2-(propylamino)ethyl group, 2-
(isopropylamino)ethyl group, 2-amino-1-methylethyl group, 2-aminopropyl group, 3-aminopropyl group, 2-hydroxy-3-aminopropyl group, 2-
(Methylamino)propyl group, 3-(methylamino)propyl group, 2-(ethylamino)propyl group, 3-(ethylamino)propyl group, 2-(propylamino)propyl group, 3-(propylamino)propyl group, 2-(isopropylamine)propyl group, 3-(isopropylamino)propyl group, 4-aminobutyl group, 4-(methylamino)butyl group, 4-(ethylamino)butyl group, 4
-(propylamino)butyl group, 4-(isopropylamino)butyl group, 5-aminopentyl group, 6-aminohexyl group, 7-aminoheptyl group, 8-aminooctyl group, 2-(2-aminoethyl)amino Ethyl group, 4-(
Examples include 3-aminopropyl) aminobutyl group.

Examples of the alkyl group for R40 include a methyl group, ethyl group, propyl group, isopropyl group, butyl group, see-butyl group, tert-butyl group, isobutyl group, amyl group, and isoamyl group, and examples of the alkenyl group include Allyl group, 2-butenyl group, 3-butenyl group, 1-
Methyl-2-propenyl group, 2-methyl-2-propenyl group, 1,2-dimethyl-2-propenyl group, 2-methyl-2-butenyl group, 3-methyl-2-butenyl group, 2
, 3-dimethyl-2-butenyl group, and -D-Y includes 2-hydroxyethyl group, 2-hydroxypropyl group, 3-hydroxypropyl group, 2-hydroxypropyl group, and -D-Y.
Examples include aminoethyl group, 2-aminopropyl group, 3-aminopropyl group, and 4-aminobutyl group.

Ro and R40 may form a ring having 3 to 8 members with the nitrogen atom to which they are bonded, and this ring may contain an oxygen atom or a nitrogen atom, and the hydrogen atom of the ring may be an alkyl group, hydroxyalkyl group, benzyl group, amino group,
It may be substituted with a formyl group, an alkoxycarbonyl group or an aminoalkyl group. Specific examples of such substituted or unsubstituted rings having 3 to 8 members include piperidino groups, and those in which the hydrogen atoms of these rings are substituted with the above-mentioned substituents. Alkyl groups that can be used as substituents for these rings include methyl, ethyl, propyl, etc., hydroxyalkyl groups include hydroxymethyl, hydroxyethyl, hydroxypropyl, etc., and alkoxycarbonyl include methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, etc. Aminoalkyl group is aminomethyl, 1
-aminoethyl, 2-aminoethyl, 1-aminopropyl, 2-aminopropyl and the like. Examples of the specific structures of these rings include examples.

Examples of the alkyl group of R'' include methyl group, ethyl group, propyl group, isopropyl group, butyl group, 5eC-butyl group,
Examples of the hydroxyalkyl group include tert-butyl group, isobutyl group, amyl group, and isoamyl group, and examples of the hydroxyalkyl group include 2-hydroxyethyl group, 2-hydroxyprocel group, and 3-hydroxypropyl group.

R'', R40 and R'' together with the nitrogen atom to which they are bonded form a bridged ring having 4 to 12 members, and this ring may contain a double bond or a nitrogen atom and may be branched. Examples include:

Specific examples of the compound of general formula (II) include those listed in Table 12.

B Table 12 R3 = R40R41N Table 12 (Continued) Table 12 (Continued) Table 12 (Continued) Table 12 (Continued) Table 12 (Continued) Table 12 (Continued) Table 12 (Continued) Table 12 (continued) Table 12 (continued) Table 12 (continued) Table 12 (continued) Table 12 (continued) When the urea compound of general formula (I) is used alone, oil and interface Composition consisting of an active agent (composition 1) or composition consisting of a surfactant (composition 2)
It is preferable to add

Examples of the oil of Composition 1 include vegetable oils such as soybean oil, cottonseed oil, corn oil, and sunflower oil, animal oils such as beef tallow and whale oil, paraffin oil, synthetic oil, and silicone oil.

As the paraffin oil, in addition to commercially available liquid paraffin, such as liquid paraffin manufactured by Wako Pure Chemical Industries, Ltd., those containing surfactants can also be used. As paraffin oil containing surfactant, for example, oleo DPII
E (Oleo DPIIB, manufactured by DuPont), Fyzol IIE (Fyzol IIB, manufactured by Chevron), Agri-Dex (manufactured by Helena)
, Atl Plus 411 (Atl) 1uS 41L IC
I Agrochemical Co.), Crop Oil Extra (
Crop Oil Extra (manufactured by Caro), Herb imax (manufactured by Loveland), Competitor 92' Crop Oil Concentrate (Competit)
erCrop Oil Concentrate, manufactured by Red Panther Chemical Co.), etc.
It can be used as it is as the above composition 1.

Furthermore, the surfactants used in Composition 1 and Composition 2 include nonionic, cationic, anionic, and amphoteric surfactants.

Examples of nonionic surfactants include mypolyoxyethylene alkyl ether, polyoxyethylene alkyl phenyl ether, polyoxyethylene fatty acid ester, polyoxyethylene polyol fatty acid ester, fatty acid sorbitan ester, fatty acid glycerin ester, and polyoxyethylene polysilane ether. Examples include silicone surfactants and fluorine surfactants.

Examples of polyoxyethylene alkyl ethers include Renex 36 (manufactured by Bayer),
Examples include Genapol X060 (Genapol X060, manufactured by Hoechst). Examples of polyoxyethylene alkylphenyl ethers include ortho x-77
Ortho X-775reader
, Chevron), Citowet
t, manufactured by BASF), coop spreader activator (COOP Spreader-Activa)
ter (manufactured by Farmland Industries), Agral 30 (manufactured by ICI Agrochemical), and the like.

When the urea compound of general formula (I) is used alone, the amount used varies depending on the type of weed, growth stage, density of growth, etc., but it is usually preferable to use 0.05 to 1.0 kg/ha. In addition, when adding the above additive, the amount added is 0.01 to 5.0%, preferably 0.01 to 5.0%, based on the volume of water when the urea compound of general formula (I) is diluted with water.
．． 02-2.0%. Similarly, the amount of the compound of general formula (I[) added is 0.01 to 5.0%, preferably 0.01 to 5.0%, based on the volume of water when the urea compound of general formula (I) is diluted with water. 02-2.0%.

When the urea compound of general formula (I) and other herbicides are used together, the amount used is usually 0.05 to 0.5 kg/ha of the urea compound of general formula (I) and 0.05 to 0.5 kg/ha of the other herbicide. is 0.
05-1. It is preferable that it is Okg/ha. In this case, the amount of the compound of general formula (II) to be added is
0 for the volume of water when diluting the urea compound with water.
．． 0.01 to 5.0%, preferably 0.02 to 2.0%.

A urea compound represented by general formula (I) used in the present invention,
Alternatively, a composition of the urea compound represented by the general formula (I) and other herbicides can be prepared by blending these active ingredients with a solvent, carrier, surfactant, dispersant, adjuvant, etc., using a conventional method, e.g. It is preferable to formulate and apply it as a wettable powder, emulsion, granule, fine granule, powder, etc. Suitable solvents here include, for example, isopropanol, xylene, toluene, methylnaphthalene, cyclohexanone, isophorone, diacetate alcohol, methyl isobutyl ketone, benzyl alcohol, N, N-dimethylformamide, N-methyl-2- Examples include pyrrolidone and hexanol. Examples of the carrier include talc, bentonite, clay, kaolin, diatomaceous earth, white carbon, vermiculite, slaked lime, silica sand, ammonium sulfate, and urea. Examples of surfactants and dispersants include alkyl sulfate ester salts, alkylbenzene sulfonates, lignin sulfonates, polyoxyethylene glycol ethers,
Examples include polyoxyethylene alkylaryl ether and polyoxyethylene sorbitan monoalkylate. Examples of the adjuvant include carboxymethyl cellulose, polyethylene glycol, and gum arabic.

A urea compound represented by general formula (I) used in the present invention,
Examples of compositions of the urea compound and other herbicides are shown below. The percentages in the examples are percentages by weight.

Formulation Example 1 (Wettable powder) A wettable powder is prepared by uniformly mixing and pulverizing 10% of the compound of general formula (I), 5% of calcium salt of higher alcohol sulfate, 4% of polyoxyethylene alkylaryl ether, and 81% of kaolin. shall be.

Formulation example 2 (hydrating powder) 6% of the compound of general formula (I), compound (a) ~ [533 ~
24%, sodium salt of higher alcohol sulfate 3
% and 88 to 67% of kaolin are uniformly mixed and ground to form a wettable powder.

Formulation Example 3 (Emulsion) 25% of the compound of general formula (I), 8% of polyoxyethylene castor oil ester, 7% of calcium dodecylbenzenesulfonate, 5% of castor oil, 20% of methylpyrrolidone and 35% of methylnaphthalene were uniformly added. Dissolve to form an emulsion.

Formulation example 4 (emulsion) 10% of the compound of general formula (I), compounds (a) to [335
~40% polyoxyethylene alkylaryl ether, 30% methylnaphthalene, and 45~10% dimethylformamide are uniformly dissolved to form an emulsion.

The compound represented by general formula (II) used in the present invention is
This compound may be used alone, but it can be mixed with a solvent, a carrier, a surfactant, a dispersant, an auxiliary agent, etc., and made into, for example, an aqueous solution, a wettable powder, an emulsion, a granule, a fine granule, a powder, etc. by a conventional method. It is preferable to formulate it and apply it. Suitable solvents here include, for example, water, isopropanol, xylene, toluene, methylnaphthalene, benzyl alcohol, N, N-
dimethylformamide, N-methyl-2-pyrrolidone,
Examples include hexanol. Examples of the carrier include talc, bentonite, clay, kaolin, diatomaceous earth, white carbon, vermiculite, slaked lime, silica sand, ammonium sulfate, and urea. Examples of the surfactant and dispersant include alkyl sulfate salts, alkylbenzene sulfonate salts, lignin sulfonate salts, polyoxyethylene glycol ether, polyoxyethylene alkylaryl ether, polyoxyethylene sorbitan monoalkylate, and the like. As an adjuvant,
Examples include carboxymethylcellulose, polyethylene glycol, gum arabic, and the like.

A blending example of the compound represented by the general formula (I[) is shown below. The percentages in the examples are percentages by weight.

Formulation Example 5 (Water Solvent) 5% of the compound of general formula (I[) and 95% of water are evenly mixed to prepare a water solvent.

Formulation Example 6 (Wettable powder) 5% of the compound of general formula (II), 3% of sodium salt of higher alcohol sulfate ester, and 92% of kaolin are uniformly mixed and ground to prepare a wettable powder.

Formulation example 7 (emulsion) 5% compound of general formula (II), 10% polyoxyethylene alkylaryl ether, 30% methylnaphthalene
and 55% dimethylformamide are uniformly dissolved to form an emulsion.

In addition, the compound represented by the general formula (IF) may be formulated with a urea compound represented by the general formula (I), or a composition of the urea compound represented by the general formula (I) and another herbicide. . A blending example in this case is shown below. The percentages in the examples are percentages by weight.

Formulation example 8 (emulsion) 20% compound of general formula (I), 20% compound of general formula (II), 8% polyoxyethylene castor oil ether, 7% calcium dodecylbenzenesulfonate, 5% castor oil, methylpyrrolidone 15% of methylnaphthalene and 25% of methylnaphthalene are uniformly dissolved to form an emulsion.

Formulation example 9 (emulsion) 10% of the compound of general formula (I), compounds [a] to [jl5
~30%, 10% compound of general formula (I[), 10% polyoxyethylene alkylaryl ether, 30% methylnaphthalene and 35-10% dimethylformamide
Uniformly dissolve it to make an emulsion.

〔Example〕

Hereinafter, the present invention will be explained in more detail with reference to Examples, Comparative Examples, and Test Examples, but these are not intended to limit the scope of the present invention in any way.

Example 1 Aqueous solvent 300■ prepared according to Formulation Example 5 containing Compound No. 404 and Formulation Example 1 containing Compound No. 1
After dispersing 50 ml of the hydrating powder prepared according to the method in 14.5 ml of water, add 150 ml of the surfactant Genabol X-060 (additive 1) as an additive to prepare a spray liquid. did. 1.5 ml of this spray liquid was sprayed on the magnetic pot shown in the test example, and a field crop herbicidal activity test was conducted. The results are shown in Table 15.

Examples 2 to 7 Similarly to Example 1, compound (II) shown in Table 12 was mixed with the compound (II) shown in Table 12 according to Formulation Examples 3 to 7, or with the compound shown in Tables 1 to 11, or this compound [a] to [jl A composition with the compound (II) was prepared according to Formulation Examples 1 to 4, dispersed or emulsified in water, and then the additives shown in Table 13 were added to prepare a spray solution [Amount of compound (II) added: 0.1%,
Amount of additive added = 1%].

Table 13 Additive 1 Kenapol X060 (Genapol
X060) Additive 2 Agridex (Agri-D
ex) Additive 3 Atplus Additive 4 Agral 90 (Agral-90) The amount of the compound shown in Tables 1 to 11 in the above spray liquid is 0.2
It was sprayed on the pots shown in the test example at an amount of 5 kg/ha. Table 15 shows the field crop herbicidal activity test results corresponding to Examples 2 to 53.

Comparative Example 1 After dispersing 50 ml of the hydrating agent prepared according to Formulation Example 1 containing compound number 1 into 14.8 ml, the surfactant Genapol X-060 (additive 1 ) was added to prepare a spray solution. A field crop herbicidal activity test was conducted by spraying 1.5 ml of this spray liquid onto the magnetic pot shown in the test example. The results are shown in Table 15.

Comparative Examples 2 to 53 Similarly to Comparative Example 1, compounds shown in Tables 1 to 11, or compositions of these compounds and compounds [al to [jl] were formulated according to Formulation Examples 1 to 4. Table 15 shows the results of a field herbicidal activity test using these spray solutions.

Test example Herbicidal activity test 1 by field crop foliage treatment /10.
Fill a 000 are magnetic pot with sifted field soil,
The fields were sown with Japanese velvet, Japanese fir tree, Datura vulgare, Japanese apricot, whiteberry, chickweed, violet, wheat, barley, and corn, and covered with 10 m of soil. After growing corn in a greenhouse until it reaches the four-leaf stage, apply the spray solution described in Examples and Comparative Examples at 1 liter per 10 are.
The foliar spray was applied from above the plant using a small sprayer at a spray volume of 50 liters. After the chemical treatment, the plants were grown in a greenhouse for another 20 days, and then the effects and phytotoxicity on each plant were investigated according to the standards in Table 14. The results are shown in Table 15.

(Margins below the essentials) Table 14 (Spaces below the essentials) [Effects of the invention] According to the present invention, the general formula (I) has a strong herbicidal effect.
The safety of the urea compound or the composition of the compound and other herbicides on crops can be increased without reducing the herbicidal effect.

Applicant: Mitsui Petrochemical Industries, Ltd. Agent Patent Attorney Yusuke Hiraki Same patent attorney Sadaji Ishii Same patent attorney Yasushi Hayakawa

Claims (1)

[Claims] General formula (I) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (I) [In the formula, Ar is a formula; ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ Numerical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ Mathematical formulas, chemical formulas,
There are tables, etc.▼, or▲There are mathematical formulas, chemical formulas, tables, etc.▼ (Here, each group of R^1 to R^1^5 and R^1^7 to R^3^8 is the same or different hydrogen Represents an atom, lower alkyl group or lower alkoxy group, R^1
^6 represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, or a hydroxyl group, provided that R^2 and R^3, R^6 and R^7, R^9 and R^1^0, R^1^ 1 and R^1^5
Alternatively, each of R^1^5 and R^1^6 is linked to represent an alkylene chain optionally substituted with a lower alkyl group, and together with the carbon atom to which they are bonded, 5 to 6
May form a membered ring, or R^1^1 and R^1^
2 may be connected to represent an ethylenedioxy group, or R^1^4 and R^1^5 may be connected to represent a dichloromethylene group),
A is a nitrogen atom or ▲There are mathematical formulas, chemical formulas, tables, etc.▼
= (where X represents a hydrogen atom, chlorine atom, nitro group or trifluoromethyl group), B represents a hydrogen atom, methyl group or methoxy group], or a urea compound represented by the general formula (I) Compositions of the expressed urea compound and other herbicides, as well as general formula (II) R^3^9R^4^0R^4^1N (II) [wherein R^3^9 has a carbon number of 1 to 8 alkyl group, a cycloalkylalkyl group having 4 to 8 carbon atoms which may be substituted with an aminoalkyl group, an alkenyl group having 3 to 6 carbon atoms, an alkynyl group having 3 to 5 carbon atoms, an amino group or an alkyl group. An optionally substituted alicyclic hydrocarbon group having 3 to 9 carbon atoms, an aralkyl group having 7 to 12 carbon atoms optionally substituted with an alkoxy group, or -C-X (wherein C is substituted with a hydroxyl group) an optionally branched alkylene group having 2 to 8 carbon atoms, X is a hydroxyl group, and 1 to 3 carbon atoms;
represents an alkoxy group, an amino group, an alkylamino group having 1 to 4 carbon atoms, or an aminoalkylamino group having 2 to 3 carbon atoms), R^4^0 is a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, Alkenyl group having 3 to 6 carbon atoms or -D-Y
(In the formula, D represents an optionally branched alkylene group having 2 to 4 carbon atoms, Y represents a hydroxyl group or an amino group), and R^3^9 and R^4^0 represent the bond between them. A ring having 3 to 8 members may be formed together with the nitrogen atom, and this ring may contain an oxygen atom or a nitrogen atom, and may include an alkyl group, a hydroxyalkyl group, a benzyl group, an amino group,
It may have a formyl group, an alkoxycarbonyl group or an aminoalkyl group as a substituent, and R^4^1
is a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, and 2 to 3 carbon atoms.
represents a hydroxylalkyl group or an aminoalkyl group having 1 to 3 carbon atoms, and R^3^9, R^4^0 and R
^4^1 may form a bridged ring having 4 to 12 members with the nitrogen atom to which they are bonded, and this ring may contain a double bond or a nitrogen atom, and may be branched. At least one compound selected from the group of compounds represented by
A herbicidal composition containing a seed compound as an active ingredient.