JPH0827091A - Carbamate derivative and herbicide containing the same as an active ingredient - Google Patents

Abstract

PURPOSE:To obtain a novel compound which is useful as a herbicide because it has excellent herbicidal effect with high selectivity between crop and weed plants. CONSTITUTION:This compound is expressed by formula I [X1 is O, S, NH; X2 is O, S; R is a halogen, a 1-4C haloalkyl, CN, NO2, a 1-4C haloalkoxy, (halogen- or CF3-substitutable) phenoxy, (halogen- or CF3-substitutable) pyridyloxy; R1 is a 1-4C (halo)alkyl; R2 is H, halogen, CN, NO2, a 1-4C (halo)alkyl, a 1-4C (halo)alkoxy; Z is CH, N; m is 1-3; n is 1-5], for example, O-[1-(3- trifluoromethylphenoxy)-3-chloro-2-propyl] N-(beta-phenethyl)-carbamate. The compound of formula I is obtained by reaction of a compound of formula II with a compound of formula III in the presence of a base.

Description

Detailed Description of the Invention

[0001]

OBJECT OF THE INVENTION The present invention relates to a carbamate derivative and a herbicide containing the same as an active ingredient.

The present inventors have conducted various studies to find out an excellent herbicide, and as a result, the carbamate derivative represented by the following general formula 2 has an excellent herbicidal effect, and some have a certain kind of crops. The present inventors have found that they exhibit excellent selectivity among weeds and have completed the present invention.

That is, the present invention has the general formula

[Chemical 2][In the formula, X₁Represents an oxygen atom, a sulfur atom or an NH group
Then X₂Represents an oxygen atom or a sulfur atom, and R represents halo.
Gen atom, C₁~ C_FourHaloalkyl group, cyano group, nit
B group, C₁~ C_FourHaloalkoxy group, phenoxy group (the
A phenoxy group is one or more halogen atoms or trif
Optionally substituted with a luoromethyl group) or pyridylo
A xy group (the pyridyloxy group is one or more halogen atoms
Or may be substituted with a trifluoromethyl group)
Represent, R₁Is C₁~ C_FourAlkyl group or C₁~ C_Four
Represents a haloalkyl group, R₂Is hydrogen atom, halogen atom
Child, cyano group, nitro group, C₁~ C_FourAlkyl group, C₁
~ C_FourAlkoxy group, C₁~ C_FourHaloalkyl group or
C₁~ C_FourRepresents a haloalkoxy group, n is an integer of 1 to 5
Represents a number, m represents an integer of 1 to 3, and Z represents a CH group.
Or represents a nitrogen atom. However, when m and n are 2 or more
Is R, R₂May be the same or different. ]]
Carbamate derivative (hereinafter referred to as the compound of the present invention)
You ) And a herbicide containing the same as an active ingredient.
In the general formula 2, R₁, R₂Halogen source in
As a child, fluorine atom, chlorine atom, bromine atom, iodine
Atom is given, R₁, R₂At C₁~ C _FourArchi
Examples of the alkyl group include a methyl group, an ethyl group and n-pro group.
Pill group, isopropyl group, n-butyl group, sec-butyl
Group, tert-butyl group and the like. R₂At C
₁~ C_FourAs the alkoxy group, for example, a methoxy group,
Ethoxy group, n-propoxy group, isopropoxy group, n
-Butoxy group, sec-butoxy group, tert-butoxy group
Etc., and R and R₂At C₁~ C_FourHaloa
Examples of the alkyl group include a trifluoromethyl group,
2,2,2-trifluoroethyl group and the like, R₁
At C₁~ C_FourAs the haloalkyl group, for example,
Chloromethyl group, bromomethyl group, trifluoromethyl group
Group, 2,2,2-trifluoroethyl group and the like,
R and R₂The haloalkoxy group in
Fluoromethoxy group, 2,2,2-trifluoroethoxy
Si group and the like. Substituent in the compound of the present invention
(R)_mThe substitution position of is preferably the 3-position, and X₁As an acid
Elementary atom is preferred, X₂Is preferably an oxygen atom,
R₁Is preferably an ethyl group.

Next, the method for producing the compound of the present invention will be described in detail. The compound of the present invention has the general formula

Embedded image [In the formula, X ₁ , X ₂ , R, R ₁ and m have the same meanings as described above. ] And a chloroformate derivative represented by the general formula:

[Chemical 4] [In the formula, R ₂ , n and Z represent the same meaning as described above. ]
It can be produced by reacting with an amine derivative represented by or a salt thereof. This reaction is usually
The reaction is carried out in the presence of a base in the absence of solvent or in a solvent, the reaction temperature range is usually 0 to 100 ° C., the reaction time range is usually instantaneous to 24 hours, and the amount of the reagent to be used in the reaction is represented by the general formula The amine derivative of the general formula 4 or a salt thereof is usually 1 to 2 equivalents, and the base is usually 1 to 3 equivalents, relative to 1 equivalent of the chloroformate derivative of 3. Examples of the solvent used as necessary include, for example, hexane, heptane, ligroin, aliphatic hydrocarbons such as petroleum ether, aromatic hydrocarbons such as benzene, toluene, xylene, chloroform, carbon tetrachloride, dichloroethane, and chlorobenzene. , Halogenated hydrocarbons such as dichlorobenzene, diethyl ether, diisopropyl ether, dioxane,
Tetrahydrofuran, ethers such as diethylene glycol dimethyl ether, acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone, ketones such as cyclohexanone, aliphatic acids such as formic acid, acetic acid, oleic acid, ethyl formate, ethyl acetate, butyl acetate, diethyl carbonate, etc. Esters, nitro compounds such as nitroethane and nitrobenzene, nitriles such as acetonitrile and isobutyronitrile, pyridine, triethylamine, N, N
-Tertiary amines such as diethylaniline, tributylamine and N-methylmorpholine, acid amides such as formamide, N, N-dimethylformamide and acetamide, sulfur compounds such as dimethylsulfoxide and sulfolane, and mixtures thereof. . Examples of the base used include organic bases such as pyridine, triethylamine and N, N-diethylaniline, inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate and sodium hydride, sodium methoxide and sodium ethoxy. Examples thereof include alkali metal alkoxides and the like. Examples of the salt of the amine derivative include inorganic acid salts such as hydrochloride, hydrobromide and sulfate. The reaction solution after completion of the reaction is subjected to usual post-treatments such as extraction with an organic solvent and concentration, and if necessary, further purified by a procedure such as chromatography, distillation, recrystallization and the like to obtain the desired compound of the present invention. be able to.

The compounds of the present invention have the general formula

Embedded image [In the formula, X ₁ , R, R ₁ and m represent the same meaning as described above. ] And an alcohol derivative represented by the general formula:

[Chemical 6] [In the formula, X ₂ , R ₂ , n and Z have the same meanings as described above. ] It can manufacture also by making it react with the isocyanate derivative shown by these. This reaction is generally carried out in the presence of a base without solvent or in a solvent, the reaction temperature range is usually 0 to 100 ° C., the reaction time range is usually 1 to 24 hours, and the reagents to be used in the reaction are The amount of is usually 1 to 2 equivalents for the isocyanate derivative of general formula 6 and 0.001 to 1 equivalent for the base, relative to 1 equivalent of the alcohol derivative of general formula 5. As the solvent used as necessary, hexane, heptane, ligroin, aliphatic hydrocarbons such as petroleum ether, benzene, toluene,
Aromatic hydrocarbons such as xylene, chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, halogenated hydrocarbons such as dichlorobenzene, diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, ethers such as diethylene glycol dimethyl ether, acetone, methyl ethyl ketone, Methyl isobutyl ketone, isophorone, cyclohexanone and other ketones, formic acid, acetic acid, oleic acid and other aliphatic acids, ethyl formate, ethyl acetate, butyl acetate, diethyl carbonate and other esters, nitroethane, nitrobenzene and other nitro compounds, acetonitrile, Nitriles such as isobutyronitrile, tertiary amines such as pyridine, triethylamine, N, N-diethylaniline, tributylamine and N-methylmorpholine, formua De, N, N- dimethylformamide, acid amides such as acetamide, dimethyl sulfoxide, sulfur compounds such as sulfolane, liquid ammonia, water and the like, or mixtures thereof. Examples of the base used include pyridine, triethylamine, N, N
-Organic bases such as diethylaniline, sodium hydroxide,
Examples thereof include inorganic bases such as potassium hydroxide, sodium carbonate, potassium carbonate and sodium hydride, and alkali metal alkoxides such as sodium methoxide and sodium ethoxide. If necessary, a catalyst such as di-n-butyltin laurate (IV) may be used. After completion of the reaction, the reaction solution is cooled to room temperature and then subjected to usual post-treatments such as extraction with an organic solvent and concentration, and if necessary, further purified by a procedure such as chromatography, distillation, recrystallization, etc. The compound of the present invention can be obtained.

Next, examples of the compounds of the present invention are shown in Tables 1 to 11 together with the compound numbers. In Tables 1 to 11, Ph
Represents a phenyl group, and Pyr represents a pyridyl group.

[Table 1] Carbamate derivative of

[0006]

[Table 2]

[0007]

[Table 3]

[Table 4]

[Table 5]

[0008]

[Table 6]

[0009]

[Table 7]

[0010]

[Table 8]

[0011]

[Table 9]

[0012]

[Table 10]

[0013]

[Table 11] The compound of the present invention has optical isomers derived from asymmetric carbon, but it goes without saying that all of these optical isomers are also included in the present invention.

When the compound of the present invention is produced, the chloroformate derivative represented by the general formula 3 and the alcohol derivative represented by the general formula 4 which are starting compounds are produced, for example, according to the following scheme 7.

[Chemical 7] [In the formula, X ₁ , X ₂ , R, R ₁ and m have the same meanings as described above. ]

The compound of the present invention has an excellent herbicidal effect,
Some also show excellent selectivity between crops and weeds. That is, the compound of the present invention has herbicidal activity against various weeds which cause the following problems in foliage treatment and soil treatment of upland fields. Polygonum convolvulus, Weed Polygonum, Polygonum convolvulus
ygonum lapathifolium), American scepter (Polygon
um pensylvanicum), Hartade (Polygonum persicari)
a), Rumex crispus, Rumex crispus
(Rumex obtusifolius), Japanese knotweed (Polygonum cuspidatu
m) Portulaca oleracea Weeds Portulaca oleracea Weeds Weeds Stellaria media Weeds Weeds Chenopodium album, Kochia scopar
ia) Amaranthaceae weeds Amaranthus retroflexus, Aconanthus amaranthus hybridus Brassicaceae weeds Wild radish Raphanus raphanistrum, Sinapis arvensis, Capsella bursa-
pastoris) Leguminous weed Legume weed (Sesbania exaltata), Ebisu grass (Cassia obtusifolia), Florida begger weed (Des
modium tortuosum), white clover (Trifolium repens) mallow weed Abutilon theophrasti, American stag deer (S
ida spinosa) Violet weeds Field pansies (Viola arvensis), Wild pansies (Viola tricolor) Rubiaceae weeds Yamgra (Galium aparine)

Convolvulaceae weeds American morning glory (Ipomoea hederacea), Malva morning glory (Ipomoea purpurea), Malva american morning glory (Ipomo)
ea hederacea var integriuscula), Yellow-faced morning glory (Ipo
moea lacunosa), bindweed (Convolvulus arven)
sis) Lamiaceae weeds (Lamium purpureum)
ium amplexicaure) Weeds of Solanaceae, Datura stramonium, Solanum nigrum, Weeds of Veronica persica and Veronica persica.
eronica hederaefolia) Weeds Asteraceae (Xanthium pensylvanicum), Wild sunflower (Hel
ianthus annuus), dog chamomile (Matricaria perforat
a), corn marigold (Chrysanthemum segetum),
Forsythia (Matricaria matricarioides), Ragweed
(Ambrosia artemisiifolia), Black ragweed (Ambrosia
trifida), Japanese barley grass (Erigeroncanadensis),
Wormwood (Artemisia princeps), Solidago serrata (S
olidagoaltissima) Weeds belonging to the family Myosotis arvensis (Weosotis arvensis) Weeds of the family Potato family (Asclepias syriaca) Weeds of the family Euphorbia helioscopia (Euphorbia maculata)

Weeds of the grass family, Echinochloa crus-galli,
aria viridis), Achinoe foxtail (Setaria faber)
i), Crabgrass (Digitaria sanguinalis), Crabgrass (Ele
usine indica), Bluegrass (Poa annua), Blackgrass (Alopecurus myosuroides), Oat (Ave)
na fatua), Seiban sorghum (Sorghum halepense),
Wheatgrass (Agropyron repens), Japanese horse chestnut (Bromus)
tectorum), Cynodon dactylon, Panicum dichotomiflorum, Texas Panicum
(Panicum texanum), Shatter cane (Sorghum vulgar
e) Commelina communis Commelina communis Commelina weed Equisetum arvense Cyperus weed (Cyperus iria), Cyperus rot
undus), Cyperus esculentus, and some of the compounds of the present invention are corn (Z
ea mays), wheat (Triticum aestivum), barley (Hor)
deum vulgare), rice (Oryza sativa), sorghum (Sorgh)
um bicolor), soybean (Glycine max), cotton (Gossypium)
spp.), sugar beet (Beta vulgaris), peanuts (Arach
is hypogaea), sunflower (Helianthus annuus), rapeseed
No major phytotoxicity against major crops such as (Brassica napus) and horticultural crops such as flowers and vegetables.

Further, the compound of the present invention has herbicidal activity against various weeds which cause the following problems in the flooding treatment of paddy fields. Weeds of grass family Echinochloa oryzicola Weeds of Sesameaceae Lindernia procumbens Weeds of the family Lythraceae (Rotala indica), Lathyrus serrata (Ammannia)
multiflora) Weeweed (Elatine triandra) Weed weed (Cyperus difformis), Firefly (Scirpus)
juncoides), pine nuts (Eleocharis acicularis), Cyperus serotinus, crocoy (Eleocha)
ris kuroguwai) Weasel weed, Kokonagi (Monochoria vaginalis) Weeds, weed Urikawa (Sagittaria pygmaea), Soda (Sagittaria)
trifolia), Heraomodaka (Alisma canaliculatum), Weed Shiro (Potamogeton distinctus), Weed Seri (Oenan the javanica) In addition, some of the compounds of the present invention cause harmful effects on transplanted rice or direct-seeded paddy rice. Not shown. Further, the compounds of the present invention can control a wide range of weeds that occur in orchards, meadows, lawns, forestry or waterways, canals or other non-agricultural lands.

When the compound of the present invention is used as an active ingredient of a herbicide, it is usually mixed with a solid carrier, a liquid carrier, a surfactant or other auxiliaries for formulation to prepare an emulsion, a wettable powder, a suspension,
Formulated in granules, concentrated emulsions, wettable granules, etc. These formulations contain the compound of the present invention as an active ingredient in a weight ratio of 0.5 to 80%, preferably 1.5 to 70%.
As the solid carrier, kaolin clay, attapulujain clay, bentonite, acid clay, pyrophyllite, talc, diatomaceous earth, calcite and other mineral fine powder, walnut shell powder and other organic fine powder, urea and other water-soluble organic substances Fine powder,
Inorganic salt fine powder such as ammonium sulfate and fine powder of synthetic silicon oxide hydroxide are listed, and the liquid carrier is methylnaphthalene, phenylxylylethane, aromatic hydrocarbon such as alkylbenzene such as xylene, isopropanol, ethylene glycol, and the like. Alcohols such as 2-ethoxyethanol, esters such as dialkyl phthalate, ketones such as acetone, cyclohexanone and isophorone, mineral oil such as machine oil, soybean oil, vegetable oil such as cottonseed oil, dimethyl sulfoxide, N, Examples thereof include N-dimethylformamide, acetonitrile, N-methylpyrrolidone, water and the like. Surfactants used for emulsification, dispersion, wet extension, etc. include alkyl sulfate ester salts, alkyl sulfonates, alkylaryl sulfonates, dialkylsulfosuccinates, polyoxyethylene alkylaryl ether phosphate ester salts, etc. Nonionic surfactants such as anionic surfactants, polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene polyoxypropylene block copolymers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, and the like. . Other formulation adjuvants include lignin sulfonate,
Alginate, polyvinyl alcohol, gum arabic,
CMC (carboxymethyl cellulose), PAP (acidic isopropyl phosphate), etc. are mentioned.

The compound of the present invention is usually formulated and subjected to soil treatment, foliar treatment or flooding treatment before or after emergence of weeds. Soil treatment includes soil surface treatment, soil admixture treatment, etc., and foliage treatment includes treatment from above the plant,
There are local treatments that treat only weeds so that they do not adhere to crops. In addition, the herbicidal effect may be enhanced by using the compound of the present invention in combination with other herbicides. Chlortol as the active ingredient of other herbicides mixed
uron, diclofop-methyl, methabenzthiazuron, mecopro
p, isoproturon, bifenox, dichlorprop, DNOC, ioxyni
l, isoxaben, chlorsulfuron, metsulfuron-methyl, fl
uroxypyr, amidosulfuron, imazamethabenz, diflufeni
can, difenzoquat, benzoylprop-ethyl, flamprop-isop
ropyl, bromoxynil, atrazine, dicamba, cyanazine, me
tolachlor, alachlor, linuron, simazine, pendimetha
lin, nicosulfuron, bentazon, primisulfuron, 2,4-D,
Examples include clopyralid, triallate, etc., but are not limited to these examples. The mixing ratio of the compound of the present invention to these other herbicides is, of course, different depending on the kind of the active ingredient of the herbicide to be mixed and the like, but is usually 1: 0.01 to 1:10 by weight. When the composition of the present invention is used as a mixture with other herbicides, usually, the compound of the present invention and each of the active ingredients of the above other herbicides are previously added in advance as a solid carrier, liquid carrier, surfactant or other formulation aid. A mixture with an agent, formulated into an emulsion, a wettable powder, a suspension, a water-soluble granule, a water-soluble powder, an aqueous solution, a wettable granule, etc., and then mixed, or the compound of the present invention and the above herbicide. It may be mixed and then mixed with a solid carrier, a liquid carrier, a surfactant, and other auxiliaries for formulation to prepare an emulsion, a wettable powder, a suspension, a granule, a concentrated emulsion, a wettable granule, or the like. Used. In these formulations, the total amount of the compound of the present invention and other herbicides as active ingredients is 0.5 to 80% by weight, preferably 1.5 to 70%.
%contains. Furthermore, the compound of the present invention can also be used as a mixture with insecticides, acaricides, nematicides, fungicides, plant growth regulators, fertilizers, soil conditioners and the like.

When the compound of the present invention is used as an active ingredient of a herbicide, the treatment amount thereof varies depending on weather conditions, formulation form, treatment time, treatment method, soil conditions, target crops, target weeds, etc., but usually 1 hectare. 10g to 8000
g, preferably 30 g to 2000 g, emulsion, wettable powder,
Suspensions, concentrated emulsions, wettable granules, liquids, etc. are usually used in a prescribed amount of 10 liters to 1000 per hectare.
Liter (added auxiliary agent such as spreading agent if necessary)
It is diluted with water and treated, and granules, certain suspensions, certain liquids and the like are usually treated as they are without any dilution. As the auxiliary agent, in addition to the above-mentioned surfactant, polyoxyethylene resin acid (ester), lignin sulfonate, abietic acid salt, dinaphthylmethane disulfonate, crop oil concentrate (crop oil concede)
ntrate), soybean oil, corn oil, cottonseed oil, sunflower oil and other vegetable oils.

[0022]

EXAMPLES The present invention will be described in more detail below with reference to production examples, formulation examples and test examples, but the present invention is not limited to these examples. First, production examples of the compound of the present invention will be shown. Production Example 1 (Production of Compound 1 of the present invention) 0.90 g of 1- (3-trifluoromethylphenyl) -2-propanol and 0.73 of β-phenethylisocyanate
g in 15 ml ether, 3 drops triethylamine,
Add 4 drops of di-n-butyltin dilaurate (IV),
The mixture was stirred at 50 ° C for 10 hours. The reaction solution was cooled to room temperature, washed with 1N hydrochloric acid, and further washed twice with water. The organic layer was dried over magnesium sulfate, ether was removed, and the residue was subjected to silica gel chromatography (developing solvent).
Hexane: ethyl acetate = 3: 1) and added O- [1-
(3-trifluoromethylphenoxy) -3-chloro-
0.90 g of 2-propyl] -N- (β-phenethyl) -carbamate was obtained. Production Example 2 (Production of compound 2 of the present invention) 1.3 g of 1- (3-trifluoromethylphenoxy) -2-butyl chloroformate and β-phenethylamine
0.90 g was dissolved in 40 ml of methylene chloride and viridine 1.4 was added.
g and stirred at room temperature overnight. Reaction solution is water, 5%
The organic layer was washed successively with hydrochloric acid and 5% aqueous sodium hydrogen carbonate solution, dried over magnesium sulfate, and then methylene chloride was removed to give O- [1- (3-trifluoromethylphenoxy) -2-butyl] -N. -(Β-phenethyl)
-1.8 g of carbamate was obtained.

Next, Table 12 shows some examples of the compounds of the present invention together with their physical properties.

[Table 12] Carbamate derivative of

Next, formulation examples are shown. The compounds of the present invention are shown by the compound numbers in Tables 1 to 11. Parts are parts by weight. Formulation Example 1 50 parts of each of the compounds 1 to 181 of the present invention, 3 parts of calcium ligninsulfonate, 2 parts of sodium lauryl sulfate and 45 parts of synthetic hydrous silicon oxide are well pulverized and mixed to obtain each wettable powder. Formulation Example 2 10 parts of each of the compounds 1 to 181 of the present invention, 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzene sulfonate, 35 parts of xylene and 35 parts of cyclohexanone are mixed well to obtain each emulsion. Formulation Example 3 2 parts of each of the compounds 1 to 181 of the present invention, 2 parts of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 64 parts of kaolin clay were well pulverized and mixed, and after adding water and kneading well. Granulate and dry to obtain each granule. Formulation Example 4 25 parts of each of the compounds 1 to 181 of the present invention, 50 parts of a 10% aqueous solution of polyvinyl alcohol, and 25 parts of water are mixed, and wet pulverized until the average particle diameter becomes 5 μm or less to prepare each suspension agent. obtain. Formulation Example 5 5 parts of each of the compounds of the present invention 1 to 181 was added to 40 parts of a 10% aqueous solution of polyvinyl alcohol, and the mixture was emulsified and dispersed by a homogenizer until the average particle size became 10 μm or less, and then 55 parts of water was added. , To obtain each concentrated emulsion. Formulation Example 6 10 parts of each of the compounds 1 to 181 of the present invention, 40 parts of isoproturon, 3 parts of calcium ligninsulfonate, 2 parts of sodium lauryl sulfate and 45 parts of synthetic hydrous silicon oxide are well pulverized and mixed to obtain each wettable powder. To get Formulation Example 7 5 parts of each of the compounds of the present invention 1 to 181, 20 parts of isoproturon, 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzene sulfonate,
25 parts of xylene and 30 parts of cyclohexanone were mixed well to obtain each emulsion. Formulation Example 8 2 parts of each of the compounds 1 to 181 of the present invention, 8 parts of isoproturon, 2 parts of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 56 parts of kaolin clay are well pulverized and mixed, and water is added. In addition, after kneading well, it is granulated and dried to obtain each granule. Formulation Example 9 10 parts of each of the compounds of the present invention 1 to 181, 40 parts of isoproturon, 35 parts of 10% aqueous solution of polyvinyl alcohol,
15 parts of water is mixed and wet-pulverized until the average particle diameter becomes 5 μm or less to obtain each suspension agent. Formulation Example 10 2 parts of each of the compounds of the present invention 1 to 181 and isoproturon 8 in 40 parts of 10% aqueous solution of polyvinyl alcohol
Parts, and the mixture is emulsified and dispersed by a homogenizer until the average particle size becomes 10 μm or less, and then 50 parts of water is added to obtain each concentrated emulsion.

Next, it is shown in Test Examples that the compound of the present invention is useful as an active ingredient of a herbicide. The compounds of the present invention are shown by the compound numbers in Tables 1-11. For the evaluation of herbicidal efficacy and phytotoxicity, "0" was used when the emergence or growth of the test plants (weeds and crops) at the time of the survey had no or almost no difference compared to that of the untreated plants. The one completely dying or the budding or the growth being completely suppressed is defined as "5" and classified into 6 stages of 0 to 5, 0,
Shown as 1, 2, 3, 4, and 5. Evaluation of herbicidal efficacy "4" and "5" means excellent herbicidal efficacy, and evaluation of "3" or less means insufficient herbicidal efficacy. Evaluation of phytotoxicity "0" and "1" means that phytotoxicity does not pose a practical problem, and rating "2" or higher means that phytotoxicity is not allowed.

Test Example 1 Paddy Water Submersion Treatment Test Soil was filled in a cylindrical plastic pot having a diameter of 9 cm and a depth of 11 cm, and seeds of the rice barnyard grass were sown. After flooding to make paddy fields, it was grown in a greenhouse for 8 days. Thereafter, the test compound was made into an emulsion according to Preparation Example 2, and a predetermined amount thereof was diluted with water,
The water surface was treated with 50 liters of the diluted solution per are. After the treatment, the plants were grown in a greenhouse for 19 days, and the herbicidal efficacy was investigated. The results are shown in Table 13.

[Table 13]

Test Example 2 A concrete container (40 × 35 cm ² ) was filled with upland soil, seeded with wheat, scabbard, Astragalus chinensis and Ordina, and 1-3 cm thick footwear was applied. According to Formulation Example 2, the test compound was made into an emulsion, and a predetermined amount thereof was diluted with water equivalent to 667 liters per hectare, and the soil surface was treated with a small sprayer. After the treatment, the plants were grown outdoors for 115 days, and herbicidal efficacy and phytotoxicity were investigated. The results are shown in Table 14.

[Table 14]

Test Example 3 A concrete container (40 × 35 cm ² ) was filled with upland soil, and wheat, honeywort, kochakobe, yaemgra,
Narcissus, Astragalus serrata, Blackgrass and Poa annua were sowed and grown for 48 days. Thereafter, the test compound was emulsified according to Formulation Example 2 or Formulation Example 7,
The predetermined amount was diluted with water equivalent to 667 liters per hectare, and the whole foliage was uniformly treated from above the plant body with a small sprayer. Weeds and crops at this time are 3 to 2
It was 0 cm. 80 days after the treatment, herbicidal efficacy and phytotoxicity were investigated. The results are shown in Table 15. The test was conducted outdoors.

[Table 15]

[0029]

Industrial Applicability The compounds of the present invention have excellent herbicidal activity against various weeds which are problematic in soil treatment and foliage treatment of upland fields, and flooding treatment of paddy fields. It is useful as an active ingredient of herbicides because it shows excellent selectivity among weeds.

 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Kazuo Saito 4-2-1 Takashi, Takarazuka-shi, Hyogo Sumitomo Chemical Co., Ltd.

Claims (2)

[Claims] 1. A compound represented by the general formula: [In the formula, X ₁ represents an oxygen atom, a sulfur atom or an NH group, X ₂ represents an oxygen atom or a sulfur atom, R represents a halogen atom, a C ₁ -C ₄ haloalkyl group, a cyano group, a nitro group, C ₁ To C ₄ haloalkoxy group, phenoxy group (wherein the phenoxy group may be substituted with one or more halogen atoms or trifluoromethyl group) or pyridyloxy group (wherein the pyridyloxy group is one or more halogen atom or trifluoromethyl group). Optionally substituted with a fluoromethyl group), R ₁ is a C ₁ -C ₄ alkyl group or C ₁ -C ₄
Represents a haloalkyl group, R ₂ represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, a C ₁ -C ₄ alkyl group, C ₁
To C ₄ alkoxy group, C _{1 to} C ₄ haloalkyl group or C _{1 to} C ₄ haloalkoxy group, n represents an integer of 1 to 5, m represents an integer of 1 to 3, Z represents a CH group or Represents a nitrogen atom. However, when m and n are 2 or more, R and R ₂ may be the same or different. ] The carbamate derivative shown by these. 2. A herbicide containing the carbamate derivative according to claim 1 as an active ingredient.