HK1236940A1 - Substituted pyrazolyl-pyrazole derivative and use of same as herbicide - Google Patents

Description

Substituted pyrazolyl pyrazole derivatives and their use as herbicides

Technical Field

The present invention relates to substituted pyrazolyl pyrazole derivatives and the use of the compounds as herbicides.

Background

In recent years, cultivation of crops has been facilitated by saving labor of crops and improving productivity of crops by using a large amount of herbicides. Many herbicides have been put to practical use in the field and rice cultivation.

However, the kinds of weeds are various, and the germination and growth periods of various weeds are different, and the occurrence of perennial weeds is long-term. It is therefore very difficult to control all weeds with one herbicide spray.

The early-medium treatment of rice with the single treatment agent was shown to be effective for treatment of wild barnyard grass (Echinochloa oryzae) and barnyard grass (Echinochloa crus-galli var. cruris), Ji-tian barnyard grass (Echinochloa crus-galli var. fortmosensis), Ji-zono crus (Echinochloa crus-galli var. practicola) and Mao-Canari crus (Echinochloa crus-galli var. caudata) up to 2-3 leaf stage, and it was shown that the treatment was effective for controlling major weeds by one treatment (see non-patent document 1). However, it is very difficult to control weeds in the period in which wild barnyard grass has grown to 3.5 leaf stage or more, and control of wild barnyard grass at 3 leaf stage and control at 3.5 leaf stage are technically isolated from each other.

Further, maintenance of the herbicidal effect (or residual effect) over a long period of time is important in reducing the number of agricultural chemical sprays, saving labor in operation, reducing costs, and the like, and is considered to be a required performance in an early-to-middle-stage single treatment agent.

In addition, ALS (acetolactate synthase) inhibitors have been widely used in recent years, and weeds resistant to ALS inhibitors have become a problem. In particular, there are few herbicides having a sufficient effect on the ALS inhibitor-resistant biotype of perennial pseudobulbus cremastrae (Sagittaria trifolia) or pseudobulbus cremastrae (Sagittaria pygmaea). Further, as weeds which have become a problem in recent years, there are exemplified, for many years: examples of the herbicides include water chestnut (Eleocharis kurouwai), Scirpus planiculmis (Scirpusplaniculmis), Scirpus triquetrum (Scirpus nipponicus), etc., and examples of the herbicides include Aeschynonensis (Aeschynomenneindica), Euphorbia lathyris (Leptochloa chinensis), verruca vulgaris (Murdannia keisak) in one year.

On the other hand, many pyrazole derivatives are put to practical use as herbicides, and for example, they are widely used: 4- (2, 4-dichlorobenzoyl) -1, 3-dimethyl-5-pyrazolyl p-toluenesulfonate (common name: "Pyrazolate)"), 2- [4- (2, 4-dichlorobenzoyl) -1, 3-dimethylpyrazol-5-yloxy ] acetophenone (common name: "Pyrazoxyfen)"), 2- [4- (2, 4-dichloro-m-toluoyl) -1, 3-dimethylpyrazol-5-yloxy ] -4' -methylacetophenone (common name: "pyrazofenap)", and the like, however, the application range of any single agent to the wild millet in Japan as a registration is up to 1.5 leaf stage, these pyrazole derivatives are effective against a wide range of weeds, but the effect on high-leaf-age wild barnyard grass is not necessarily sufficient.

Further, 1- (3-chloro-4, 5,6, 7-tetrahydropyrazolo [1,5-a ] pyridin-2-yl) -5- [ methyl (prop-2-ynyl) amino ] pyrazole-4-carbonitrile (common name: "Pyraclonil (Pyraclonil)", trade name Pyraclon) which is the compound of example 4.73 described in patent document 1 is effective against a wide range of weeds, but the effect on high-leaf-age wild barnyard grass is not sufficient, and the range of application of the present single agent to wild barnyard grass is up to 1.5 leaf stage in registration in japan.

Further, patent document 1 also discloses compounds which exhibit herbicidal effects on weeds growing in a field by pre-and post-emergence treatments, but there is no description about the leaf age, and these compounds cannot be said to have sufficient effects on weeds of high leaf age. In addition, as a herbicide exhibiting a wide-ranging herbicidal effect against weeds in a field, for example, isopropylammonium N- (phosphonomethyl) glycine ester (common name: "glyphosate isopropylamine salt") has been widely used, but in recent years, problems have been encountered such as the occurrence of resistant weeds.

In addition, in recent years, a problem of pollution of groundwater and river water due to agricultural chemicals has occurred. Therefore, development of herbicides which minimize environmental influences, such as low possibility of effusing the active ingredients from places other than the application sites, is being pursued.

Documents of the prior art

Patent document

Patent document 1: WO94/08999

Non-patent document

Non-patent document 1: the ecology of weeds in paddy fields and the control thereof-explanation of weeds and herbicides in rice-159.

Disclosure of Invention

Problems to be solved by the invention

The object of the present invention is to provide a compound having the following excellent characteristics as a herbicide ingredient: has a broad herbicidal spectrum including weeds resistant to conventional herbicides, can control important weeds of higher leaf age which are practically problematic, and does not cause phytotoxicity to crops such as rice.

Means for solving the problems

The present inventors have conducted extensive studies to achieve the above object, and as a result, have found that a pyrazolylpyrazole derivative having a specific chemical structure exhibits excellent herbicidal efficacy against high-leaf-age important weeds while having a broad herbicidal spectrum particularly over a long period of time, and on the other hand, has sufficient safety against cultivated crops, and have completed the present invention based on such findings.

Accordingly, the present invention provides a pyrazolyl pyrazole derivative of the compound represented by the following formula (I).

[ chemical formula 1]

In the above formula, the first and second carbon atoms are,

R¹represents a chlorine atom or a bromine atom,

R²represents a cyano group or a nitro group,

R³represents (optionally substituted by 1 or more halogen atoms) C₁~C₆Alkyl, fluorine atom, chlorine atom, bromine atom, and

a represents 3 to 5.

In the formula (I), preferred is:

R¹represents a chlorine atom, and represents a chlorine atom,

R²represents a cyano group, and represents a cyano group,

R³represents (optionally substituted by 1 or more halogen atoms) C₁~C₄An alkyl group, a chlorine atom, a bromine atom,

a represents 4.

In the present specification, "C" preceding each substituent_a~C_bThe "description" means that a to b carbon atoms are present in the group.

"halogen atom" includes fluorine, chlorine, bromine and iodine atoms.

The "alkyl" referred to in the group itself or a part of the group may be linear or branched, and is not limited, and examples thereof include: methyl, ethyl, n-or i-propyl, n-, i-, s-or t-butyl, n-pentyl, n-hexyl and the like, each selected within the range of the number of carbon atoms specified.

At least 1 of the hydrogen atoms included in the "alkyl group" may be substituted with a halogen atom, and for example, in the case of an alkyl group, the number of the carbon atoms is not limited, but may be selected from the group consisting of chloromethyl, dichloromethyl, trifluoromethyl, chloroethyl, dichloroethyl, trifluoroethyl, tetrafluoropropyl, bromoethyl, bromopropyl, chlorobutyl, chlorohexyl, and perfluorohexyl, each of which has a specified number of carbon atoms.

In the case where the aforementioned group or moiety is multiply substituted by halogen atoms, the group may be substituted by more than 1 of the same or different halogen atoms.

In all the formulae listed below, the substituents and symbols have the same meanings as defined in formula (I) unless otherwise defined. The invention provides a compound of formula (I) wherein R³The compound having a hydrogen atom can be easily synthesized by amidation of the compound represented by the formula (II).

[ chemical formula 2]

The compounds of formula (II) may be synthesized from tetrahydro-2H-pyran-2-ylideneacetonitrile or 5-chlorovaleryl chloride according to the procedures described in WO93/10100 and WO 94/08999.

The amidation reaction of the compound of the formula (II) can be carried out by itself with reference to well-known reaction conditions (for example, refer to WO94/08999, Tetrahedron Lett. 32, 4019 (1991)).

The compounds of formula (I) provided by the present invention have excellent herbicidal effects and are useful as herbicides, as shown by the results of the herbicidal activity tests described in test examples 1 to 4 described below.

The compounds of formula (I) of the present invention are active against a variety of agro-and non-agro-weeds. Examples of the cultivated plants include gramineous plants such as rice, wheat, barley, corn, oat, and sorghum; or broad-leaved crops such as soybean, cotton, beet, sunflower and rape seed, vegetables such as fruit trees, fruit vegetables, root vegetables and leaf vegetables, lawn fields, etc., and can be used for cultivation thereof.

The compound of the present invention has herbicidal effects against various weeds which are problematic in paddy fields as listed below in any of soil treatments with or without flooding, soil mixing treatments, and foliage treatments. The weeds are exemplified below, but are not limited to these examples.

As paddy field weeds which can be controlled by the compound of formula (I) of the present invention, for example: alismaceae weeds such as Alisma orientalis (Alisma canariculatum), Pseudobulbus Cremastrae (Sagittaria trifolia), and Pseudobulbus Cremastrae (Sagittaria pygmaea); cyperaceae weeds such as Cyperus difformis (Cyperus difformis), Cyperus serotinus (Cyperus serotinus), Iris lactea (Scirpus juncoides), Eleocharis buchae (Eleocharis kurogua), Scirpus planiculmis (Scirpus planiculmis), Scirpus triquetrum (Scirpus niponicus), etc.; scrophulariaceae weeds such as stranguria (Linderniaprocumbens), Dombia subspecies of North American mother grass (Lindernia dubia subsp. dubia), and Lindernia dubia; weeds of the family Potentilla fruticosa, such as Monochoria variegalis (Monochoria korsakowii), and Potentilla rainiana (Monochoria korsakowii); weeds of the family of the ophthalmocaceae such as eyeweed (Potamogeton sativus); lythraceae weeds such as herba Aristolochiae Japonicae (Rotala indica) and Ammannia multiflora (Ammannia multiflora); compositae weeds such as Bidens tripartita and Bidens frontosa; legume weeds such as Aeschynomene indica; weeds of Commelinaceae such as verruca (Murdannia keisak); gramineae weeds such as field barnyard grass (Echinochloa oryzae), canine barnyard grass (Echinochloa crus-galli var. crus-galli), Ji-tian barnyard grass (Echinochloa crus-galli var. fortmosensis), Ji-tian barnyard grass (Echinochloa crus-galli var. practicola), Mao-kyo barnyard grass (Echinochloa crus-galli var. calvata), Euphorbia lathyris (Leptochloachinensis), pseudorice (Leersia japonica), Paspalum distichum (Paspalum sativum), Ronga serrulata (Leersiazoides) and the like.

In addition, as for various weeds which have problems listed below, the treatment methods of the field and non-agricultural land all have herbicidal effects in any of the soil treatment, the soil mixture treatment, and the foliage treatment. The weeds are exemplified below, but are not limited to these examples.

Examples thereof include: solanaceous weeds such as black nightshade (Solanum nigrum) and Datura stramonium (Datura stramonium); malvaceae weeds such as Abutilon Avicennae, Sida spinosa, Convolvulus arvensis, and Abutilon indicum; convolvulaceae weeds such as Ipomoea purpurea; amaranth weeds such as Amaranthus (Amaranthus lividus), Amaranthus retroflexus (Amaranthus retroflexus), Amaranthus praecox (Amaranthus palmeri), Amaranthus tuberosus (Amaranthus tuberosus), and the like; weeds belonging to the family of Compositae, such as Xanthium sibiricum (Xanthium strumarium), Ambrosia artemisiifolia (Ambrosia artemisiifolia), Astraria ciliata (Galinsoga cirata), Cirsium setosum (Cirsium arvense), Senecio vulgaris (Senecio vulgaris), annual fleabane (Stenacosis annuus), Echinacea pallida (Galinsoga parviflora), sowthistle (Sonchusa arvensis), Sonchusa arvensis (Sonchusoleraceus), and Chamomile (Matricaria inodora); cruciferous weeds such as Indian Rorippa indica (Rorippa indica), wild mustard (Sinapis arvensis), Capsella bursa-pastoris (Capsella bursaris) and Thlaspi arvense (Thlaspi arvense); polygonaceae weeds such as Polygonum caninum (Persicaria longissieta), Polygonum convolvulus (Fallopia convoluulus), Polygonum aviculare (Polygonum aviculare var. condensatum), Polygonum aviculare (Polygonum aviculare var. mongoliense), Polygonum vernalium (Polygonum persicum), Polygonum elongatum (Polygonum lapathiocara), Polygonum macrocarpum (Polygonum lapathiocarpa), and Polygonum macrocarpum (Persicaria lapathifolia. incana); portulacaceae weeds such as Portulaca oleracea; chenopodiaceae weeds such as Chenopodium album (Chenopodium album), Chenopodium album (Chenopodium fiscifolium), Kochia scoparia (Kochia scoparia), and Chenopodium Atriplex (Atriplex patula); caryophyllaceae weeds such as chickweed (Stellaria media); scrophulariaceae weeds such as Veronica persica (Veronica persica); commelina communis (Commelina communis) and other Commelina communis family weeds; lamiaceae weeds such as Lamium amplexicaule (Lamium amplexicaule), Lamium purpureum (Lamium purpureum), and Moringa oleifera (Galeopsis tetrahit); euphorbiaceae weeds such as Euphorbia humifusa (Euphorbia pacifica) and Euphorbia maculosa (Euphorbia maculota); rubiaceae weeds such as cleavers (Galiumspurium), humulus eightiens (Galium spurium var. echinospermon), Rubia cordifolia (Rubia argyi), and Rubia aurantifolia (Galium aparine); pansy (pansy) weeds such as philippine violet herb (Viola mandshurica), wildlife herb (Violaarvensis), and the like; weeds of the family Boraginaceae such as forgetmenot-grass (Myosotis arvensis); broad-leaved weeds such as leguminous weeds including Sesbania exaltata and Cassia tora (Cassia obfusitolia); sorghum (Sorghum bicolor), Sorghum bicolor (Panicum dichotomiforum), Sorghum halepense (Sorghum halepense), Canarium album (Echinochloa crus-galli var. cruris), Digitaria pinnata (Digitaria ciliaris), Avena sativa (Avena fatua), Eleusine indica (Eleusine indica), Setaria viridis (Setaria viridis), Polygala viridis (Alopecurus aequalis), Poa pratensis (Poa annua), Agropyron serpyllum (Agropyron reptiles), Cynodon dactylon (Cynodon dactylon), Digitaria sanguinalis (Digitaria sanguinalis), Setaria viridis (Setaria puua), and Euphorbia hirta major (Alopecurus giraldii); cyperaceae weeds such as Cyperus rotundus (Cyperus rotundus).

Furthermore, wide-range weeds occurring in harvested plots, fallow fields, tree fields, pastures, lawn areas, rail edges, vacant lands, forestry lands, or agricultural lands, ridges, and other non-agricultural lands can be weeded.

Furthermore, the compound of formula (I) of the present invention shows no phytotoxicity which is problematic for rice in any cultivation method such as direct seeding cultivation or transplant cultivation of rice.

The compound of formula (I) of the present invention may be applied to plants before and after germination, and may be mixed in soil before sowing.

The amount of the compound of formula (I) of the present invention to be administered may vary widely depending on the kind of the compound, the kind of the target plant, the application time, the application place, the nature of the desired effect, and the like, but about 0.01 to 100g, preferably about 0.1 to 10g, is exemplified as the active compound per 1 acre on a rough basis.

The compound of formula (I) of the present invention may be used alone, but it is not limited thereto, and formulation aids and the like are usually blended into the compound of formula (I) according to a conventional method, but it is preferably used in any form, for example, as a powder, an emulsion, an oil agent, a cosolvent, a suspoemulsion, a fine granule, a spray, a DL powder, a fine granule F, a granule, a hydrate, a particulate hydrate, a flowable agent, a large particle (Jumbo) agent, a tablet, a paste, an oily suspension, an aqueous solvent, a particulate aqueous solvent, a liquid, a microcapsule, and the like.

Formulation auxiliaries that can be used in the formulation are not limited, and include, for example: solid carriers, liquid carriers, adhesives, tackifiers, surfactants, antifreeze agents, preservatives, and the like.

Examples of the solid carrier include, but are not limited to: talc, bentonite, montmorillonite, kaolin, calcium carbonate, sodium bicarbonate, mirabilite, zeolite, starch, acid clay, diatomaceous earth, white carbon, vermiculite, slaked lime, plant powder, alumina, activated carbon, sugars, glass hollow bodies, silica sand, ammonium sulfate, urea, and the like.

The liquid carrier is not limited, and examples thereof include: hydrocarbons (e.g., kerosene, mineral oil, etc.); aromatic hydrocarbons (e.g., toluene, xylene, dimethylnaphthalene, phenylxylylethane, etc.); chlorinated hydrocarbons (e.g., chloroform, carbon tetrachloride, etc.); ethers (e.g., dioxane, tetrahydrofuran, etc.); ketones (e.g., acetone, cyclohexanone, isophorone, etc.); esters (e.g., ethyl acetate, ethylene glycol acetate, dibutyl maleate, etc.); alcohols (e.g., methanol, n-hexanol, ethylene glycol, etc.); polar solvents (e.g., N-dimethylformamide, dimethylsulfoxide, N-methylpyrrolidone, etc.); water, and the like.

The adhesive and the tackifier are not limited, and examples thereof include: dextrin, sodium salt of carboxymethyl cellulose, polycarboxylic acid-based high molecular compound, polyvinylpyrrolidone, polyvinyl alcohol, sodium lignosulfonate, calcium lignosulfonate, sodium polyacrylate, gum arabic, sodium alginate, mannitol, sorbitol, bentonite-based mineral, polyacrylic acid and its derivative, white charcoal, natural sugar derivative (e.g., xanthan gum, guar gum, etc.), and the like.

The surfactant is not limited, and examples thereof include: anionic surfactants such as salts of fatty acid salts, benzoic acid salts, alkylsulfosuccinic acid salts, dialkylsulfosuccinic acid salts, polycarboxylates, alkylsulfuric acid ester salts, alkylsulfuric acid salts, alkylarylsulfuric acid salts, alkyldiethylene glycol ether sulfates, alcohol sulfuric acid ester salts, alkylsulfonic acid salts, alkylarylsulfonic acid salts, arylsulfonic acid salts, ligninsulfonic acid salts, alkyldiphenylether disulfonic acid salts, polystyrenesulfonic acid salts, alkylphosphoric acid ester salts, alkylarylphosphoric acid salts, styrylarylphosphoric acid salts, polyoxyethylene alkyl ether sulfuric acid ester salts, polyoxyethylene alkylaryl ether sulfuric acid ester salts, polyoxyethylene alkyl ether phosphoric acid salts, polyoxyethylene alkylaryl phosphoric acid ester salts, salts of formalin condensates of naphthalenesulfonic acid, and the like, and sorbitan fatty acid esters, glycerin fatty acid esters, fatty acid polyglycerin esters, fatty acid alcohol polyglycol ethers, polycarboxylic acid esters, and the like, Nonionic surfactants such as acetylene glycol, acetylene alcohol, oxyalkylene block polymers, polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene styrylaryl ethers, polyoxyethylene glycol alkyl ethers, polyoxyethylene fatty acid esters, polyoxyethylene sorbitan fatty acid esters, polyoxyethylene glycerin fatty acid esters, polyoxyethylene hydrogenated castor oil, and polyoxypropylene fatty acid esters.

The antifreeze is not limited, and examples thereof include: ethylene glycol, diethylene glycol and propylene glycol, glycerol, and the like.

The preservative is not limited, and examples thereof include: benzoic acid, sodium benzoate, methyl paraben, butyl paraben, isopropylmethylphenol, benzalkonium chloride, chlorohexidine hydrochloride, hydrogen peroxide water, chlorohexidine gluconate, salicylic acid, sodium salicylate, zinc pyrithione, sorbic acid, potassium sorbate, dehydroacetic acid, sodium dehydroacetate, phenoxyethanol, isothiazolin derivatives such as 5-chloro-2-methyl-4-isothiazolin-3-one, 2-bromo-2-nitropropane-1, 3-diol, and salicylic acid derivatives.

The above-mentioned solid carrier, liquid carrier, adhesive, tackifier, surfactant, antifreezing agent and preservative may be used each alone or in an appropriate combination according to the purpose of use and the like.

The blending ratio of the compound of formula (I) of the present invention to the entire herbicidal composition of the present invention may be optionally increased or decreased without particular limitation, and is usually about 0.01 to 90% by mass, and for example, when it is prepared into a powder or a granule, it is preferably about 0.1 to 50% by mass, and more preferably about 0.5 to 10% by mass; the amount of the surfactant is preferably about 0.1 to 90% by mass, more preferably about 0.5 to 50% by mass, in the form of an emulsion, a hydrate, or a granular hydrate.

These preparations can be applied to various uses by spraying or directly applying the preparations to plant stems and leaves, soil, water surface of paddy field, etc., after being diluted to an appropriate concentration as required.

The invention is illustrated by the following examples.

Examples

EXAMPLE 1 preparation of N- (1- (3-chloro-4, 5,6, 7-tetrahydropyrazolo [1,5-a ] pyridin-2-yl) -4-cyanopyrazol-5-yl) heptylamide (Compound 1)

Acetonitrile (200ml) was added to 5-amino-1- (3-chloro-4, 5,6, 7-tetrahydropyrazolo [1,5-a ] pyridin-2-yl) pyrazole-4-carbonitrile (36.8g), heptanoyl chloride (25.0g) was slowly added dropwise thereto, and heating and refluxing were performed for 1 day. After completion of the reaction, water was added to the reaction solution, followed by extraction with ethyl acetate. After washing with a saturated aqueous sodium bicarbonate solution, the mixture was dried over sodium sulfate, and the solvent was distilled off under reduced pressure. To the obtained crude product, hexane (100ml) and isopropyl ether (50ml) were added, and the mixture was stirred for 3 hours in an ice bath. The solid which had precipitated was washed with isopropyl ether to obtain the objective compound (35.2 g).

The starting material of formula (II) was synthesized according to WO93/10100 and WO 94/08999.

The examples listed in the following table were produced in the same manner as in the above-described method or obtained in the same manner as in the above-described method.

[ Table 1]

TABLE 1

Formulation examples

1. Powder preparation

By mixing

10 parts by weight of a compound of the formula (I)

Talc 90 parts by weight

Mixing and micro-pulverizing with hammer mill.

2. Hydrating agent

By mixing

10 parts by weight of a compound of the formula (I)

Polyoxyethylene alkyl aryl ether sulfate 22.5 parts by weight

67.5 parts of white charcoal

Mixing, and micronizing the mixture with hammer mill.

3. Flowable agent

By mixing

10 parts by weight of a compound of the formula (I)

10 parts by weight of polyoxyethylene alkyl ether phosphate

5 parts of bentonite

Ethylene glycol 5 parts by weight

70 parts by weight of water

Mixing and pulverizing using a wet pulverizer to obtain a flowable agent.

4. Emulsion formulation

By mixing

15 parts by weight of a compound of the formula (I)

Ethoxylated nonylphenol 10 parts by weight

75 parts by weight of cyclohexanone

Mixing to obtain emulsion.

5. Granular formulation

Will be provided with

5 parts by weight of a compound of the formula (I)

Calcium lignosulfonate 3 parts by weight

Polycarboxylate 3 parts by weight

89 parts by weight of calcium carbonate

Mixing, adding water, kneading, extruding and granulating. Then, the granules are dried and granulated.

< bioassay example >

1. Weeding test in paddy field

Paddy field soil was filled in a pot of 1/10000 acres, appropriate amounts of water and chemical fertilizers were added and mixed, and seeds of barnyard grass, monochoria vaginalis and japanese iris were sown while maintaining the water-filled state at a depth of 3 cm.

A hydration agent of the target compound (I) shown in table 1 prepared according to the formulation example was diluted with an appropriate amount of water, and rice at 2.0 leaf stage was transplanted to wild barnyard grass at 3.5 leaf stage, and was treated dropwise using a pipette so as to give a prescribed dose per 10 acre.

Then, after management in a glass room having an average air temperature of 30 ℃ for 30 days, their herbicidal effects were investigated.

The herbicidal effect was evaluated by comparing the growth inhibition rate (%) with that of the non-treated area, and the phytotoxicity was evaluated by comparing the growth inhibition rate (%) with that of the completely herbicidal area, and is shown in the following 11 stages.

0 (index): 0 to less than 10 percent (growth inhibition rate),

1: more than 10% and less than 20%,

2: more than 20% and less than 30%,

3: more than 30% and less than 40%,

4: more than 40% and less than 50%,

5: more than 50% and less than 60%,

6: more than 60% and less than 70%,

7: more than 70% and less than 80%,

8: more than 80% and less than 90%,

9: more than 90% and less than 100%,

10：100%。

The results are shown in Table 2.

Control agent 1.37 (described in WO 94/08999)

[ chemical formula 3]

Control agent 4.188 (described in WO 94/08999)

[ chemical formula 4]

Contrast agent 4.191 (described in WO 94/08999)

[ chemical formula 5]

[ Table 2]

TABLE 2

2. Field cultivation soil treatment test

The pots of 1/6000 acres were filled with field soil, and seeds of red crab grass, quinoa, and amaranthus retroflexus were sown and covered with soil.

A hydration agent of the compound of formula (I) shown in table 1 prepared according to the formulation example was diluted with water to a predetermined amount, and the surface layer of each soil was uniformly sprayed with a spray water amount of 100 liters per 10 acres before weed emergence after sowing.

Then, after the management in a glass room having an average air temperature of 30 ℃ for 30 days, their herbicidal effects were investigated.

The herbicidal effect was evaluated in the same manner as in test example 1.

The results are shown in Table 3.

[ Table 3]

TABLE 3

3. Test for stem and leaf treatment in field cultivation

The pots of 1/6000 acres were filled with culture soil, the seeds of the crab grass, the quinoa and the amaranthus retroflexus were sown and covered with soil, and the seeds were cultivated in a glass room at an average temperature of 25 ℃.

At the time when the l-digitaria sanguinalis grew to 1.0 to 2.0 leaf stage, the hydration agent of the target compound (I) shown in table 1, which was prepared according to the formulation example, was diluted with water to a predetermined amount, and sprayed uniformly on weeds at a spray water amount of 150 l per 10 acre.

Then, after managing for 3 weeks in a glass room having an average air temperature of 25 ℃, their herbicidal effects were investigated.

The herbicidal effect was evaluated in the same manner as in test example 1.

The results are shown in Table 4.

[ Table 4]

TABLE 4

4. Test for stem and leaf treatment in field cultivation

Soil was filled in pots of 1/4500 acres, seeds of crabgrass and achyranthes bidentata (galinoga parviflora) were sown and covered with soil, and the plants were cultivated in a glass chamber at an average temperature of 25 ℃.

In the period of time when the l-digitaria sanguinalis grew to 4-5 leaves (10-15 cm of weed height), the hydration agent of the compound of formula (I) shown in table 1, which was prepared according to the formulation example, was diluted with water to a predetermined amount, and sprayed uniformly on the weeds at a spray water amount of 100 l per 10 acre.

Then, after the management in a glass room at an average temperature of 25 ℃ for 20 days, their herbicidal effects were investigated.

The herbicidal effect was evaluated in the same manner as in test example 1.

The results are shown in Table 5.

[ Table 5]

TABLE 5

Industrial applicability

According to the present invention, the compound of formula (I) of the present invention is useful as a harmful plant control agent because it has an excellent control effect on undesired plants.

Claims (7)

1. A compound represented by the following formula (I):

in the formula (I), the compound is shown in the specification,

R¹represents a chlorine atom or a bromine atom,

R²represents a cyano group or a nitro group,

R³represents C optionally substituted by 1 or more halogen atoms₁~C₆Alkyl, fluorine atom, chlorine atom, bromine atom,

a represents 3 to 5.

2. The compound of claim 1, wherein,

R¹represents a chlorine atom, and represents a chlorine atom,

R²represents a cyano group, and represents a cyano group,

R³represents C optionally substituted by 1 or more halogen atoms₁~C₄An alkyl group, a chlorine atom, a bromine atom,

a represents 4.

3. A herbicidal composition comprising a herbicidally effective amount of at least one of the compounds of claim 1 or 2.

4. The herbicidal composition of claim 3, further comprising a formulation adjuvant.

5. A method of controlling undesired vegetation, which comprises applying an effective amount of at least 1 of the compounds of claim 1 or 2 or the herbicidal compositions of claims 3 or 4 to the locus of the undesired vegetation or undesired vegetation.

6. Use of the compound of claim 1 or 2 or the herbicidal composition of claim 3 or 4 for controlling undesired plants.

7. The use according to claim 6, wherein the compounds according to claim 1 or 2 are used for controlling undesired vegetation in crops of useful plants.