JPS5815950A - Benzoylphenylurea derivative - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

DETAILED DESCRIPTION OF THE INVENTION This invention relates to two groups of novel 1-substituted penzoyl-3-substituted phenylureas useful as herbicides.

The use of herbicides to control unwanted plant growth has been the subject of much research for many years.

Such control has economic value in many cases in agriculture. However, continuous use of chemical herbicides poses many problems such as environmental pollution, crop tolerance, weed resistance and economics. Accordingly, the ongoing development of new herbicides that are economical and selectively toxic to undesirable plants continues.

1-Benzoyl-1-phenylureas useful as herbicides have been described in the literature. Pillon et al., U.S. Pat. No. 3,384,473, discloses various 1-phenyl-
1-Benzoylureas have been described as useful as herbicides. U.S. Pat. No. 3, 3 to Lehureau et al.
No. 42,586 discloses a wide range of ureas with herbicidal activity, or teaches only 1-phenyl-1-alkanoylureas as preferred compounds. U.S. Patent No. 4466,124 and Dutch Patent No. 7,
No. 105,350 discloses various 1-(2) having insecticidal activity.
, 6-cyhalobenzoyl)-3-phenylureas.

Compounds according to the invention have the formula: [wherein both R1 are the same and are methyl or ethyl, and when both R2 and 13 are the same and are methoxy, chlorine or bromine, all hydrogen There is,
When either k and 3 are fluorine, the other is hydrogen and all 4 or hydrogen, and when both R2 and R3 are fluorine, each 4 is independently fluorine or hydrogen. ].

Among the compounds represented by formula (I), preferred compounds are compounds in which k is methyl and compounds in which R3 is fluorine.

The present invention also provides a herbicidal method using the above novel compound or a composition containing the same, and a method for producing the novel compound.

The 2,6-sialkoxybenzoylphenylureas of formula (I) are prepared by methods currently known in the art. This process consists of reacting a 2,6-dialkoxybenzoyl compound of the formula: with a substituted benzene of the formula: % where kl, R2, k:3 and R4 are has the same meaning, either Ql or (2 is -NH2,
The other is incyanate].

A preferred method of preparation is to react a 2,6-dialkoxybenzoyl derivative with anhydrous ammonia to obtain the corresponding benzamide. This benzamide is then reacted with oxalyl chloride of the formula (
6) is obtained, which is finally reacted with a suitably substituted benzene of formula (2) in which 92 is amino to give the corresponding 1-(2, 6-dialkoxybenzoyl)-3-(fi
t-substituted phenyl)urea is obtained. This method is shown in the reaction formula below.

OR1 (, R1 to 2 [In the above formula, kl, R2, R3 and k have the same meanings as above, and X represents halogen, hydroxyCl-66 alkoxy or 0-CO-(C1-C6 alkyl)]
The final step of this reaction is usually carried out in a suitable solvent under an inert atmosphere, for example under a nitrogen atmosphere. A suitable temperature range for adding the reactants is 0-30"C, preferably 10-25"C when Ql is incyanate.Q
When l is an amine, the temperature is preferably 25 to 100°C. Suitable solvents include ethyl acetate, benzene and most /10 generated solvents, methylene chloride, 1.
2-dichloroethane, chloroform and the like are preferred solvents.

Typically, the reaction temperature after adding the reactants is between about 20"C and about 4"C.
0"c. If Ql is amino, a tertiary amine base such as triethylamine or pyridine may be present. The reaction mixture is then worked up in a conventional manner. Usually the precipitated solid The product is collected or the solvent is removed under reduced pressure. If the solvent needs to be removed, the product is slurried in a suitable solvent, usually an alcohol, and the solids are collected. This product is recycled. Further purification may be achieved by crystallization or column chromatography.

The starting materials, substituted anilines and acid chlorides, are commercially available or can be easily prepared by known methods.

Typical methods for producing the starting materials used to produce the compound of formula (I) are illustrated below.

200 g of 2.6-simethoxybenzoyl chloride were added to 2.54 g of diethyl ether and the solution was cooled to 5° C. under nitrogen atmosphere. Remove nitrogen gas and reduce temperature to 5-1
NH3 gas was bubbled through the solution for 2 hours while maintaining the temperature at 0°C. Stirring was continued for 1 hour while increasing the temperature to about 25°C. The pH of the solution was 9.0. The solid material was taken from the door, put into water 21 to form a slurry, and ammonium hydroxide was added to adjust the pH of the slurry to 8.0. The solids were filtered again, washed with water and dried. Yield 16.7
g (92%).

This material could be used as is in the next step.

Production 2,6-Simethoxybenzamide 167 in nitrogen atmosphere
g was slurried in toluene 21. To this solution was added 145 g of oxalyl chloride over 1 hour. The solution was heated to 60°C and kept at this temperature - overnight. HCI gas was released while preventing water from condensing into the reaction mixture. The reaction mixture was heated at reflux temperature (approximately 110 °C) for 1
It was heated for 1/2 hour, during which time nitrogen gas was bubbled under the surface of the mixture through the gas inlet tube. Stirring was continued while the temperature of the mixture was reduced to approximately 30°C. The solution was filtered through incubator earth under nitrogen atmosphere and the solvent was removed under reduced pressure. Yield 185g (97%). This oil was stored under nitrogen atmosphere.

A compound of formula (I) can be prepared by stirring a suitable 2,6-sialkoxybenzoyl isocyanate and a substituted aniline. Examples are given below.

Example 1 1-(2,6-simethoxybenzoyl)-3
-(2,6-dichlorophenyl)urea 16.2 f of 2,6-dichloroaniline was added to 200 ml of 1,2-dichloroethane in a flask at about 25°C in a nitrogen atmosphere.
It was dissolved in To this was added 25 g of 2,6-simethoxybenzoyl isocyanate in 25 d of 1,2-dichloroethane, and after the addition was complete, the solution was stirred for 40 hours for 2 hours.
Warmed to °C.

When the mixture was subjected to thin layer chromatography on silica gel (developing solvent: ethyl ether), it was found that no 2,6-dichloroaniline remained. The solvent was removed under reduced pressure and the residue was slurried in methanol. The solids were collected and washed with methanol. Yield: 26.517 (
72%) Single element analysis (as C16H□4C1,2N204) -
, -C, HN Theoretical value: 52.02 3.82 7.59 Actual value: 51.81 3.69 7.36NM
R (δ value): 3,8 (s, 5) (, 2 0CH3),
6.7 (d, 2H, H at P position of ring), 7.4 (m, 4
H, ring (7) 4H), 10.1 (s, I H,
N'H), 10.9 (S, lH, NH) Example 2 1-(2,6-Simethoxybenzoyl)-3
-(2,6-difluorophenyl)urea 2,6-cyfluoroaniline 60f was dissolved in 1500 m of methylene chloride and cooled to 10°C. Under a nitrogen atmosphere, 90 g of 2,6-simethoxybenzoyl isocyanate in 200 ml of methylene chloride were added dropwise and the mixture was stirred at 25°C for 3 hours. The solids were collected and washed with water. The P solution was evaporated to dryness and diluted with diethyl ether 150 resistant and ethanol 150 resistant.
%) M, P, = 199-200°C Elemental analysis (as C□6H04F2N204) Theoretical value:
57.15 4.20 8.33 Actual value:
57.20 4.36 8.33 The following compound was produced by the method of Example 2.

Example 3 1-(2,6-simethoxybenzoyl) -
3-'(2,6-dibromophenyl)urea M, p,
-214~215°C Elemental analysis (as C□6H□4Br2N204) CHN Theoretical value: 41.95 3,08 6.12 Actual value: 4189 2.93 5.98 methoxybenzoyl)-3-(2
,6-Simethoxyphenyl)urea M, P, -208~
210°C Elemental analysis (as C08H2oN206) Theoretical value:
59.99 5.59 7.77 tiger and
Σ Actual value: 59.70 5.39 7.63
Example 5 1(2,6-Simethoxybenzoyl)-3-
(2-fluorophenyl)urea M, P, -207-2
09°C - Elemental analysis (as C□6H□5FN204) Theoretical value' 60,37 4.75 880 Actual value:
60.26 4.67 8.88 Example 6 1
-(2,6-Simethoxybenzoyl)-3-(2,4,
6-) Lifluorophenyl) urea M, P, = 202-203”C Elemental analysis (C16■] as 13F3N204) 9
H Theoretical value: 54.24 3.70 7.91 Actual value: 54.50 3.81 8.21 Example 7l-(2,6-dinitoxybenzoyl)-3-(2
,6-difluorophenyl)urea M, P, = 129
~130°C Elemental analysis (as C□8H□8F2N204) Theoretical value:
59.34 4.98 7.69 Actual value: 5
9.08 5.10 7.52 The following compounds were prepared by the method of Example 1.

Example 8l-(2,6-simethoxybenzoyl)-3
-(2,3,5,6-titrafluorophenyl)urea M, P, = 183.5-187''C Elemental analysis (as C□6H□2F4N204).

Theoretical value: 51.62 3,25 7.53 Actual value: 51.44 3.29 7.64 Formula (
The novel compound of the present invention represented by I) exhibits herbicidal activity against various weeds both before and after germination. The compound may be applied directly to young plants, but is preferably applied to the soil before the plants germinate. The compound may also be mixed into the soil using a conventional disc harrow prior to sowing the seeds of the desired grain, or may be applied to the soil surface prior to plant germination. In the latter case, the compounds are simply introduced into the soil, such as by rainfall. formula(
The compounds of I) have activity against various weeds such as those listed below: Chenopodium album, Amaranthus retroflexu
s), Onamomi (Xantium orienta)
le ), Butakusaku Ambrosia artem
isiifolia), morning glory (Da
turastramonium), Asakao (Ip
omoea purpurea), mehishiha (Dig
itaria 5anquinalis), Echinochloa crusgalli,
Mustard (Brassicajuncea), Enokorogusaku5etaria viridis), Karasumugi (Avena sa'tivo), Chibi (Abu
tilonthe$rasti), zinnia (Zinn
ia elegans), Suberihiyu (Portul
aca oleracea), prickly fern (p.
rickly 5ida (5ida 5pinosa)
)), Panicum, dicho
Lomiflorum), devils beggarticks (Bi
densfrondosa)), Ephlipta (ec
lipta (Ecliptajuncea)),
blackgrass (Alope)
curus myosuroides ), catchweed be
dstraw (Galiumaparine))
, Wild Chikara Mitsu L/ (Matricaria cham
omilla), ordinary hakohe (5tellaria)
media), Hard Eye Speedo x 7L/
(birdseye speedwell l (Ue
ronica persica)), Blister starch (Acanthospermum hispi)
dum), Southern 5
anbur (Cenchrus echinatus)
)), Yaemugura (Eleusine 1ndic)
a), 5-zil color lily (brazil ca
lalily (Richardia brasil)
iensis)), nightshade (ni ghts)
hade (Solanum spp.

)), and many other undesirable weeds and grass plants.

The compounds of formula (I) according to the invention are safe for a wide variety of desirable plant groups and have unique selectivity. Depending on the concentration of active compound used, some typical examples of relatively tolerant plants include: Corn Ze.
a mays), wheat (Tri ti cumae)
stivum), rice (Oryza 5ativa)
, barley (Hordeum vulgare), soybean (Glycine 1nax), cotton (Gossyp)
ium hirsutum), sugar corn S
orghum vulgare v, sacchara
tum), pea (Pisum sativum)
), Murasaki Delicious MedicagOsari
va), cucumber (Cucumis 5ativus)
), Tomato (Lycopersicon escu
lentum), peanut (Ar, achis
hypogaea), sugar beet (Beta vulg)
aris), oil rape seeds (Brassica napu)
s ), cabbage (Brassica olerac
ea capitata), turnip (Brassic)
arapa) etc.

The invention also provides a method for controlling undesired plant growth, which comprises applying an herbicidally effective amount of a compound of formula (I) to the location where plant growth is to be controlled. This is what we provide.

The above-mentioned "amount effective to exhibit herbicidal activity" refers to the amount of the compound of formula (I) that kills or stimulates the growth of the weeds to be controlled. This amount usually ranges from about 0.056 to 0.056 benzoylphenylurea per hectare.
It is approximately 16.8 kq. More preferably, this compound is applied at a rate of about 0.28 to about 8.96 kQ/ha (7). The exact concentration of compound required will vary depending on the type of weed to be controlled, the type of formulation, soil type, climatic conditions, etc.

Also, "undesirable plants" refers to weeds and their seeds that are present in the area to be treated with the compound of formula (I). The compounds according to the invention can be applied to the soil and weed seeds are selectively controlled by contacting the soil as they germinate. 'Also, the compound of the present invention can be brought into direct contact with the exposed parts of weeds to directly kill germinated weeds.

The compounds of the invention may be formulated with suitable agriculturally acceptable carriers or diluents.

Such preparations: Well, depending on the type, the active ingredient is about 0.
Contains 1 to about 95%. Sprayable formulations are preferred from the standpoint of rapidity and economy of dispersion.

Powder compositions containing the compound of formula (I) typically contain from about 0.1% to about 10% of the compound. Dusts are fine particles containing the compounds of the present invention together with an inert solid, such as crushed montmorillonite clay, attapulgite clay, rilluc, crushed volcanic rock, kaolin clay, or other inert, relatively dense, authentic material. Manufactured by grinding and mixing thoroughly.

Most formulations containing compounds of formula (I)
is a concentrated composition that is sprayed in the form of an aqueous dispersion or emulsion, containing from about 0.1% to about 10% of the compound. Compositions that can be dispersed or emulsified in water may be solid (commonly known as wettable powders) or liquid (commonly known as emulsions).

A typical hydrating agent consists of an intimate mixture of a compound of formula (I), an inert carrier and a surfactant. The concentration of active compound is usually from about 25 to about 90% by weight.

The inert carrier is usually selected from attapulgite clay, montmorillonite clay, diatomaceous earth or refined silica salt. Effective surfactants included in the wettable powder from about 0.5 to about 10% by weight are selected from sulfonated lignins, condensed naphthalene sulfonates, and alkyl sulfates.

from about 12 to about 720 g of compound of formula (I) per 11 liquids dissolved in the liquid. The organic solvent is selected based on its solvent ability and cost. Useful solvents are aromatic, especially xylenes and heavy aromatic naphthas. Other organic solvents such as terpene solvents and kerosene may also be used. Suitable emulsifiers for the emulsions are selected from alkylbenzenesulfonates, naphthalenesulfonates, nonionic surfactants such as polyoxyethylene adducts of alkylphenols, and can be used in the same proportions as for the wettable powders.

Solid compositions, granular compositions are suitable for applying to soil a compound of the formula
Contains 0% by weight. Granular compositions may be prepared by using a granular inert carrier, such as coarsely ground particles having a particle size of from about 0.1 to
The compound of formula (I) is dispersed on a clay of about 3 WM. Most conveniently, the compound is dissolved in an inexpensive solvent, medium, and the solution is applied to the sized clay in a suitable solids mixer.

The formulated compounds are applied to plants in the usual manner in the field of agrochemistry. Sprayable compositions can be applied using any type of sprayer used in the art. Spraying can be effectively achieved using a self-propelled, tractor-mounted towed sprayer that dispenses the water-dispersed formulation through a graduated spray nozzle.

Metered applicators may also be used, which allow precisely measured amounts of the composition to be applied to the soil. The operator of this @Hisoujiji only needs to adjust the amount of aqueous dispersion or granule formulation to be applied per hectare, thereby uniformly distributing the compound to the plants to be treated. be done.

Examples of typical herbicide compositions according to the present invention are listed below.

Wettable powder 1 (2,6-simethoxybendiyl)-3-(2,4,6-triconcave...
50.0 Fluorophenyl) Urea Igepal (Nonionic wetting agent, ...... 5.0 GAF Corporation) Polyphon 0 (Lignosulfonate... 5.0 Dispersing agent, Westvaco: l - Poration) Theorex 7 (Precipitated Sodified Silica Increase...... 5.0 Sentence, JoM, Huber: l-Volley'iion) Bird 7 (Bardens) Clay 35. .

100.0 The above ingredients are mixed and finely ground to obtain a free-flowing powder which can be suspended in water and suitably sprayed. Of course, all compounds of formula (I) can be formulated as described above.

Aqueous suspension component Concentration (wt%) 1-(2,6-
(cymethoxybenzoyl)-3-(2,6-cyclolov...Ribration/45.
00 enyl) ureaborifone H (anionic lignosulfonate wetting agent and dispersing agent, ・・・・・・・・・ 5
．． 00Westvaco Corporation) Min-
u-gel 200 (clay type...
2.00 Gelling Agent, ]'he Floridian Compa
ny) Antifoam C (antifoaming agent, Dow...0.05 Corning Cobo L/-Water: z) Water
4795100
．． 00 The above ingredients are thoroughly mixed and pulverized to obtain a suitable suspension, which is further diluted with water at the time of application. Any compound of formula (I) can be used in the preparation of this formulation.

Powder 1 component a degree (weight %) 1-' (2,
6-Simethoxybenzoyl) -3-'(2,3,5,"6-tetra...
・・・・・・・・・ 5.0 Fluorophenyl) Urea Diatomite (Diatomite, Witc.

Ganicku Special Cheese Division) 100.0 Mix benzoyl phenyl urea and diatomaceous earth well,
Grind to a uniform fine powder with a particle size of about 16 to about 40 microns. The powder thus obtained can be applied by conventional methods, for example by aerial spraying. Of course, the formula (I
) can all be used in the preparation of this formulation.

Granule component Concentration (wt%) 1'-(2,6
-Simethoxybenzoyl) -3,-(2,3,5,6-tetra ・Song...
・・5.0 fluorophenyl) urea heavy aromatic naphtha ・・・・・・・・・
5.0 (The Floridian Company
y) 100.0 The herbicidal active ingredient is dissolved in naphtha and sprayed onto the clay granules, usually with stirring. The granules are passed through a sieve to obtain granules of uniform size. Of course, all compounds according to the invention can be formulated in this type.

The herbicidal activity of representative compounds represented by formula (I) is summarized below.

Test 1 The compound of formula (I) has herbicidal activity. Initial herbicidal activity tests were carried out at a compound concentration of 16.8 kt)/ha. In this test, a standard sand:soil (1:1) mixture was autoclaved and sterilized at approximately 118°C for 24 hours. After sterilization, this soil mixture was placed in separate containers and seeds of Tomato, Mehishiha and Obiyu were planted in a row. Each container was fertilized using a 23-21-17 fertilizer for 4 days prior to treatment.

A formulation for spraying was prepared by dissolving test compound 2 (1) in 2 ml of solvent. The solvents were Tokushimaru R1,174q and Tokushimaru S Q, 783
micalCompany, Northfield
, a unique mixture of anionic and nonionic surfactants manufactured by Linois, Inc.) in acetone 1
00- and ethyl alcohol 100 tu1! It was prepared by putting it in. Add 8ml of this solvent/compound solution to deionized water! 0 modified Devilbiss diluted to
Germinated this solution using a sprayer? Sprayed after rIJ and germination. Post-germination treatment is carried out from 11 to 13 after sowing the seeds.
After 1 day, pre-emergence treatment was carried out 1 day after sowing the seeds.

After treatment, the containers were transferred to a greenhouse and watered as needed. Observations were made for 10-13 days after treatment, based on untreated control plants. The degree of herbicidal activity was determined by rating the treated plants on a scale of 1-5. Here, 1 represents damage O, 2 represents slight damage, 3 represents moderate damage, 4 represents severe damage, and 5 represents plant death or non-germination.

The type of damage for each test plant was coded as follows:

A- leaf detachment, B- fading, C- whitening, D- death, E-
Clay figurine growth, F group system effect, G = BF green, I - plant growth enhancement, L - local necrosis, he - no germination P - purple pigment formation, k
The herbicidal activity of a typical 2゜6-dialkoxopenzoylphenylurea of formula (I) was investigated based on the secondary herbicidal activity test of ``decreased germination, S-growth ejection, and -other damage.'' The results are shown in Table 1 below.

Test 2 The herbicidal activity of the compound group of formula (■) against several plant species was investigated in a greenhouse at various dosage rates. Several weeds and crops were used to determine the herbicidal activity and selectivity of the test compounds. The test compound was formulated in the same manner as above. However, the test compound is approximately 4y/EOOm
Approximately 1 part of this organic solution was diluted with 12 parts of water before being dissolved in a surfactant-containing solvent in a proportion of 1.35 g and applied to containers containing seeds.

Table 2 shows the results of the pre-emergence herbicidal activity test when spraying at a rate of 8.96 y/ha or lower.
Table 3 shows the results of the post-emergence herbicidal activity test when sprayed at a rate of /ha.

The compound of the example, 1-(2,6-simethoxybenzoyl)-3-(2,6-difluorophenyl)urea, was subjected to field tests to determine its herbicidal activity and crop tolerance.

This test compound was formulated into a 50% permanent formulation in the following manner. Compound 127.2y of Example 2 was treated with Reax (
Reax) 45L (surfactant with action as wetting agent and dispersant + lignosulfonate, Westva
co) 19.8y, Zeolex
7 (precipitated silica, J.M., Huber, Cor.
p.

) 12.3g and Barden'
5clay) (Kaolinite L/I, J, M
, HuberCorp) 87,7t. This mixture was ground to the desired size in a hammer grinder or fluid energy grinder.

The formulated compound was diluted with water and administered to a range of crops and weeds at various application rates. The administration method was surface spraying and pre-contamination before planting.

The degree of crop damage was visually graded on a scale of 0 to 10 (
0 = no damage, 10 = plant death, and this value was multiplied by 10 to determine percent inhibition).

The test was repeated three times at each application rate, and the average percentage inhibition is shown in Table 4. Observations were made 3 and 6 weeks after planting (and treatment). The results of this field test in the case of surface spraying are shown in Table 4, and the results in the case of previous planting are shown in Table 5.
Shown below. In the table, a dash (-) indicates that the test was not conducted under the applicable conditions.

Test 4 Field tests were carried out in British Law to investigate the action and selectivity of the compound of Example 2 against a wide variety of crops and weeds. The compound was formulated as previously described using ΔToximar and S as surfactants and a 1:1 mixture of acetone:ethanol. This formulation was sprayed on the soil surface before germination. The growth of crops, namely barley and wheat, is observed and the effects of compounds on these plants are determined by comparing the germination of the crops against an untreated control group and by determining their ability to control certain weed species. did. The control rate was based on visual inspection and expressed as a percentage compared to the untreated control group. The results are shown in Table 6 below.

Table 6 (Table 6 pecking) (Table 6 continued) (Table 6 continued) (Table 6 continued) As already mentioned, compounds of formula (I) may be used together with one or more herbicides. good. Use of such a combination is suitable when a broader spectrum of weed control is desired than when each is used alone.

For example, the compounds of the invention can be mixed with one or more herbicides. Preferred herbicides used in these combinations are dinitroanilines, such as trifluralin, benefin, butraline, chlornisine, dinitramine, etalfluralin, flufloralin, inproparin, nitraline, oryzalin, bendimethalin, prodiamine, promethrin, prosul. Farin etc. The most preferred combination of the present invention is trifluralin and 1-(2,6-simethoxybenzoyl)-3-(2
, 6-difluorophenyl) urea. Other herbicides used in combination with the benzoylureas described herein include alachlor, ametrine, amitrole, atrazine, pentacine, bifenox, butachlor, butam, putidazole, butyrate, chloramben, chlorbromulon, cyanazine. , dichlorprobe, diuron, dinoceb, EPT
C, phenac, fluometuron, linuron, metazole, metolachlor, metribuzin J nitrofen, norflurazone, peplate, verfluidone, promethone, promethrin, propachlor, simazine, tebutiuron, tilbutrin, trialate, triclopil, propanil, perlut, etc. It will be done.

Accordingly, the present invention also provides a method for controlling undesirable plants comprising applying to the plants a combination of benzoyl phenyl urea of formula (■) and other herbicides in an amount effective to inhibit the growth of the plants. This is what we provide. The desired application rate of individual herbicides in combination depends on many factors,
This will depend, for example, on the types of weeds and grasses to be controlled, the herbicides used in the combination, the climate and soil conditions, the amount of weeds, etc. Generally, the compounds of this invention are used in a ratio of about 1 to about 10 parts by weight of benzoylphenyl urea to about 10 to about 1 part by weight of the other herbicide.

A more preferred proportion of active ingredients is about 1 compound of formula (I)
~5 parts by weight and about 5 to about 1 part by weight of other herbicides. A particularly preferred combination includes these herbicidal active ingredients in a ratio of about 1:
1 (weight ratio). Application of effective amounts of the above combinations can provide the desired degree of control of undesirable plants.

The mixtures described above can be formulated in the same way - and at similar concentrations - as the compounds of the invention alone.

Each of the active ingredients of the combination may be mixed with each other to formulate the mixture as a whole, or may be formulated individually and applied to unwanted plant habitats as a combination or separately. May be sprayed.

Typical herbicidal compositions containing the above combinations are illustrated below.

Triflurali 40 formulated as 1-(2,6-Simethoxybenzoyl)-3-(2,6-difluoro 60.0 phenyl)urea (50% permanent agent) 4F,C (4 lb/gal, emulsion) ,07
(Triflural in) 100.0 A hydrating agent containing 50% by weight of the active ingredient is added to water and the mixture is mixed into an emulsion containing trifluralin at a rate of 4 lb/gal (480 f/I). This mixture is spread over the soil surface and then worked in before planting, usually to a depth of about 3 to 4 inches.

The herbicidal activity of representative combinations according to the present invention was investigated in the following field test.

Test 5 A field test was conducted using a combination containing trifluralin and the compound of Example 2 as active ingredients. 50% of the compound of Example 2 as a permanent agent was added to the water under stirring;
To this mixture was added 4 lb/gal of trifluralin.
A formulation used in this test was prepared by mixing and formulating these compounds in a tank by mixing an emulsion containing the compound at a ratio of 80 y/l). This combination was incorporated into the pre-plant soil to a depth of 3 inches and soybeans and cotton were planted on the same day. Data are expressed as % inhibition. The test results are shown in Table 7 below.

Test 6 The combination of the compound of Example 2 and trifluralin was used to determine its effect on cotton and a wide range of weeds in field trials in Mississippi. This combination was formulated by tank mixing and mixed prior to planting as described above, and crops were sown on day 5 while treated in this manner. The results of the test are shown in Table 8 below.

(Table 8 continued) (Table 8 continued) (Table 8 continued) (Table 8 continued) Test 7 To examine the herbicidal activity and crop tolerance of the compound of Example 2 and the combination of this compound with etalfluralin or oryzalin Field tests were conducted in Brazil.

In both tests, the compound of Example 2 was formulated in a 50% permanent formulation.

A combination of the compound of Example 2 and oryzalin was formulated in an aqueous suspension containing the active silicon component at a rate of 4 pounds per gallon (480 g/f) (7). In this test, the formulation was mixed in a tank and applied to the soil surface after planting.

The combination of etalfluralin and the compound of Example 2 is
The active ingredient was formulated in the form of an emulsion containing 3 lbs./calon (360 y/l) and diluted with water to obtain a tank mix composition. This formulation was applied to the flexible teeth after planting. It was mixed into the soil using a shaped harrow.The treated and untreated plots were compared and observed with the naked eye.

Table 9 shows the test results for the combination of the compound of Example 2 and etalfluralin, and Table 10 shows the test results for the combination of the compound of Example 2 and oryzalin.

(Go to) Table 9. Combination of the compound of Example 2 and etalfluralin (Table 9) Table 10 Combination of the compound of Example 2 and oryzalin (Table 10
Continued)

Claims (1)

[Claims] 1. Formula: [In the formula, both R are the same and are methyl or ethyl, and when both k and 13 are the same and are methoxy, chlorine or bromine, all 4 or hydrogen, k
When either one of and 3 is fluorine, the other is hydrogen, all 4 are hydrogen, and when both R2 and 3 are fluorine, each 4 is independently fluorine or hydrogen] The compound shown in 2. The compound according to item 1, wherein R1 is methyl and R2 and 13 are both fluorine. 3.1-(2,6-Simethoxybenzoyl)-3-(2
,6-dichlorophenyl)urea, 1-(2,6-simethoxybenzoyl)'-3-(2,6-difluorophenyl)urea, 1-(2,6-dimethoxybenzoyl)-3-(2, 6-dibromophenyl)urea, 1-(
2,6-Simethoxybenzoyl)-3-(2,6-Simethoxyphenyl)urea, 1-(2,6-Simethoxybenzoyl)-3-(2-fluorophenyl)urea,
1-(2,6-simethoxybenzoyl)-3-(2,4
, lotrifluorophenyl)urea, 1-(2,6-
dinitoxybenzoyl)-3-(2,6-difluorophenyl)urea and 1-(2,6-simethoxybenzoyl)-3-'(2,3,5,6-titrafluorophenyl)urea The compound according to item 1 selected from: In formula C, both 1 are the same and are methyl or 3 ethyl, and when both k and k are the same and are methoxy, chlorine or bromine, all 4 or hydrogen, R and When one of R3 is fluorine, the other is hydrogen, all 4 are hydrogen, and when both R2 and 3 are fluorine, R4 is each independently fluorine or hydrogen. A method for producing a compound represented by the formula 20RI, which comprises reacting a 2,6-dialkoxybenzoyl compound represented by the formula 20RI with a substituted benzene represented by the formula: [In the above formula, one of Ql and Q2 is -NH2, and the other is
23 represents incyanate, and R, R, R and ni4 have the same meanings as above]. 5, Formula: %Formula% [In the formula, both R1 are the same and are methyl or ethyl, and if both R2 and 3 are the same and are methoxy, chlorine or bromine, then all 4 are hydrogen, and when either one of R2 and 3 is fluorine, the other is hydrogen, all 4 are hydrogen, and when both R2 and 3 are fluorine, R4 is each independently fluorine or hydrogen] 1-(2,6-dialkoxybenzoyl)-
1. A method for controlling the growth of undesirable plants, which comprises applying an effective amount of a 3-(substituted phenyl)urea derivative to exhibit herbicidal activity to a location where plant growth is to be controlled. 6, Formula: %Formula% [In the formula, both 1 are the same and are methyl or ethyl, and when both R2 and 3 are the same and are methoxy, chlorine or bromine, all 4 is hydrogen, and when either one of R2 and 13 is fluorine, the other is hydrogen, and when both R2 and 3 are fluorine, R4 is each independently fluorine or hydrogen] 1-(2,6-dialkoxybenzoyl)-
3-(substituted phenyl)urea derivative as the active ingredient, 1
A herbicidal composition comprising one or more agriculturally acceptable carriers or diluents. 7° Formula 'ORI R3R4 [wherein both R1 are the same and are methyl or ethyl, R2
If both of 1-(2,6-dialkoxybenzoyl)-
A herbicidal composition comprising a 3-(substituted phenyl)urea derivative and another herbicide, and one or more agriculturally acceptable carriers or diluents. 8. The herbicidal composition according to item 7, wherein the other herbicide is dinitroaniline. 9. Dinitroaniline or trifluralin, Benefin,
9. The herbicidal composition according to item 8, which is butraline, chlornisine, dinitramine, etalfluralin, flufloralin, inproparin, nitraline, oryzalin, benzimethalin, prodiamine, profluralin or prosulfarin. 10. The herbicidal composition according to item 9, wherein the dinitroaniline is trifluralin. 11. The herbicidal composition according to item 7, wherein the compound of formula (I) is 1-(2,6-simethoxybenzoyl)-3-(2,6-'difluorophenyl)urea. 12. The herbicide composition according to item 11, wherein the other herbicide is trifluralin.