WO1994002449A1 - Derive de carbamate et herbicide le contenant comme ingredient actif - Google Patents

Derive de carbamate et herbicide le contenant comme ingredient actif Download PDF

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WO1994002449A1
WO1994002449A1 PCT/JP1993/001019 JP9301019W WO9402449A1 WO 1994002449 A1 WO1994002449 A1 WO 1994002449A1 JP 9301019 W JP9301019 W JP 9301019W WO 9402449 A1 WO9402449 A1 WO 9402449A1
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Prior art keywords
compound
group
carbon atoms
test example
alkyl group
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PCT/JP1993/001019
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English (en)
Japanese (ja)
Inventor
Kazuyuki Takahashi
Seiji Tomita
Hiroyuki Murakami
Hideki Kamano
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Idemitsu Kosan Co., Ltd.
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Application filed by Idemitsu Kosan Co., Ltd. filed Critical Idemitsu Kosan Co., Ltd.
Priority to AU45849/93A priority Critical patent/AU4584993A/en
Priority to KR1019950700320A priority patent/KR950702526A/ko
Publication of WO1994002449A1 publication Critical patent/WO1994002449A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/12—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/20—N-Aryl derivatives thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/22—O-Aryl or S-Aryl esters thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/14—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by halogen atoms or by nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/62—Compounds containing any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylcarbamates
    • C07C271/64—Y being a hydrogen or a carbon atom, e.g. benzoylcarbamates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D263/18—Oxygen atoms
    • C07D263/20—Oxygen atoms attached in position 2
    • C07D263/22—Oxygen atoms attached in position 2 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to other ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/16—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by esterified hydroxyl radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/36—Compounds containing oxirane rings with hydrocarbon radicals, substituted by nitrogen atoms

Definitions

  • the present invention relates to a novel carbamate derivative and a herbicide containing the same as an active ingredient.
  • Herbicides are extremely important for labor saving in weed control and for improving productivity of agricultural and horticultural crops.Therefore, research and development of herbicides have been actively conducted for many years, and a wide variety of chemicals are currently in practical use. Has been However, even today, there is a need for the development of new drugs with even more excellent herbicidal properties, especially those that can selectively control target weeds at low doses without causing phytotoxicity to cultivated crops. .
  • Similar compounds having herbicidal activity include, for example, compounds represented by the formula described in JP-B-53-37409.
  • JP-B-53-37409 The compound represented by the formula (I) described in JP-B-53-37409 is already practically used as a herbicide for controlling grass weeds in corn fields. However, when used as a rice herbicide, poor selectivity may cause harm to rice.
  • the compound represented by the formula (II) described in the above-mentioned Japanese Patent Application Laid-Open No. 1-5087336 is excellent against paddy field weeds such as nobie, evening magayari, mizugayari and annual broadleaf weeds.
  • the herbicidal effect requires relatively high doses and is not always satisfactory for practical use.
  • an object of the present invention is to provide a novel compound having excellent herbicidal activity against paddy weeds, capable of efficiently removing paddy weeds with a low dose, and capable of suppressing phytotoxicity to paddy rice extremely low.
  • An object of the present invention is to provide a herbicide contained as an active ingredient.
  • the present inventors have noted that the above-mentioned known compounds have herbicidal activity against grasses, and have excellent herbicidal activity and selectivity against other paddy weeds such as annual weeds such as grasshoppers. Devoted research has been conducted on derivatives having.
  • a novel derivative having a fuunil skeleton and a carbamate group bonded to this phenyl skeleton via a carbon atom is useful for waterweeds such as nobies, evening magallaris, mizugayari, and annual broadleaf weeds.
  • Excellent herbicidal effect and high selectivity Based on this finding, it was found that it has excellent selectivity between genus of paddy rice and Nobie and can efficiently remove paddy weeds with a low dose and has little phytotoxicity to rice.
  • the present invention has been completed.
  • the present invention relates to the general formula
  • X represents a halogen atom or a haloalkyl group having 1 to 4 carbon atoms
  • Y represents a halogen atom.
  • R 1 , R 4 , and R 5 represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms
  • R 2 represents a hydrogen atom, an alkyl group or a methoxethyl group having 1 to 4 carbon atoms
  • R 3 represents a carbon atom.
  • the carbamate derivative represented by the general formula () is a novel compound, and specifically, A, B, X, Y, R 1 , R 2 , R 3 , R 4 , R 5 and R 6 in the formula
  • the explanation is as follows.
  • X is a halogen atom or an alkyl group having 1 to 4 carbon atoms.
  • the halogen atom include fluorine, chlorine, bromine, and iodine.
  • the haloalkyl group having 1 to 4 carbon atoms include a group in which an alkyl group having 1 to 4 carbon atoms is substituted with one or two or more of the above halogen atoms, for example, a halomethyl group, a haloethyl group, a halopropyl group, a halobutyl group. Is mentioned.
  • Y is a halogen atom.
  • halogen atoms include fluorine, chlorine, bromine, iodine Prime c
  • R 1 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
  • examples of the alkyl group having 1 to 4 carbon atoms include a methyl group, an ethyl group, a propyl group, and a butyl group.
  • R 2 is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or a methoxyl group.
  • examples of the alkyl group having 1 to 4 carbon atoms include a methyl group, an ethyl group, a propyl group, and a butyl group.
  • R 3 is an alkynole group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, a methoxyethyl group or a phenyl group.
  • examples of the alkynole group having 1 to 6 carbon atoms include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, and a hexyl group.
  • haloalkyl group having 1 to 4 carbon atoms examples include a group in which an alkyl group having 1 to 4 carbon atoms is substituted with one or more of the above halogen atoms, for example, a halomethyl group, a haloethyl group, a halopropyl group, and a haloptyl group. ⁇ No.
  • R 4 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
  • examples of the alkyl group having 1 to 4 carbon atoms include a methyl group, an ethyl group, a propyl group, and a butyl group.
  • R 5 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
  • examples of the alkyl group having 1 to 4 carbon atoms include a methyl group, an ethyl group, a propyl group, and a butyl group.
  • R ° is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms
  • alkyl groups 6 to 6 include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, and a hexyl group.
  • haloalkyl group having 14 carbon atoms examples include a group in which an alkyl group having 1 to 4 carbon atoms is substituted with one or two or more of the above-described halogen atoms, for example, a halomethyl group, a haloethyl group, a halopropyl group, and a halobutyl group.
  • C14 alkoxy group examples include a formyl group, an acetyl group, a propionyl group, and a butyrinole group.
  • the methyl group may be abbreviated as Me
  • the ethyl group may be abbreviated as Et-n-propyl group
  • the n-Pri-propyl group may be abbreviated as i-Prn-butyl group
  • the n-But-butyl group may be abbreviated as t-Bu. is there.
  • carbamate derivative of the present invention represented by the general formula ( ⁇ 1) include those listed in Tables 1 to 3.
  • the carbamate derivative of the present invention has an enantiomer based on a quaternary carbon of a benzyl moiety, an oxysilane moiety, and a 7K acid moiety, and is usually obtained as a racemic form, but is obtained by a known method such as asymmetric synthesis. It is also possible to obtain each enantiomer.
  • the carnomate derivative of the present invention may be in a racemic form or in each enantiomer alone, each of which can be used as a herbicide.
  • each diastereomer can be obtained by a known method such as column chromatography.
  • the compounds of the present invention may be a mixture of diastereomers or each diastereomer alone, each of which can be used as a herbicide.
  • polyhaloalkene derivatives (IV) (compounds (IVa), (IVb) and (IVc) in Table 1) are represented by the following formula: It can be produced using the propene derivative (V) as a raw material.
  • polyhaloalkene derivative (IV) or polyhaloalkane derivative (VI) is obtained by reacting at a temperature in the range of the boiling point for 1 to 2 hours. In this case, the reaction may be led directly to the polyhaloalkene derivative (IV) or to the polyhaloalkane derivative (VI) by appropriately selecting the reaction conditions.
  • polyhaloalkane derivative (VI) When the polyhaloalkane derivative (VI) is obtained, it is placed in a solvent such as 0-dichlorobenzene, 1,2-dichloroethane in the presence of a catalyst such as cuprous chloride or ferric chloride. By heating to an appropriate temperature, a desired polyhaloalkene derivative (IV) can be obtained.
  • a solvent such as 0-dichlorobenzene, 1,2-dichloroethane
  • a catalyst such as cuprous chloride or ferric chloride.
  • the oxosilane derivative (VII) (compound (Vila), compound (Vllb) and compound (Vile) in Table 2) is a polyhaloalkene as shown in the following formula.
  • the derivative (IV) can be produced by epoxidation using a peroxide.
  • peroxide used in this reaction there is no particular limitation on the peroxide used in this reaction, and those usually used for the epoxidation of ethylenic double bonds, such as cumene-hyperoperoxide, t-butyl-hy-dropperoxide, cyclohexyl-hydroperoxide, peracetic acid, ⁇ - Perorganic powers such as hydroperoxyisobutyric acid, perbenzoic acid, m-chloroperbenzoic acid, and other powers that can use ruponic acid, hydrogen peroxide, and oxone (peroxy-sulfuric acid). Among them, perorganic carboxylic acids, particularly peracetic acid and m-chloroperbenzoic acid are preferred.
  • the reaction is usually carried out in an inert solvent, preferably from 0 to 80. Performed at temperatures in the range of C.
  • an inert solvent for example, halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, dichloromethane, 1,1,1-trichloroethane and o-dichlorobenzene are preferably used.
  • a buffer such as sodium acetate, sodium benzoate, disodium hydrogenphosphate, lithium carbonate or the like may be added to the reaction system to carry out the reaction.
  • the peroxide in a ratio of 1 to 4 equivalents to the argen derivative (IV).
  • the reaction time varies depending on the reaction temperature, the type of peroxide used, and the like, and cannot be determined uniquely, but is usually about 1 to 50 hours.
  • the halogenohydrin derivative (VIII) (compound (ViIla) and compound (VIlib) in Table 3; ne))
  • a polyhaloalkene derivative (IV) as a raw material, as shown by the following formula.
  • N-bromosuccinic acid imide or N-chloro succinic acid imid is usually added to polyhaloalkane derivative (IV) in an inert solvent such as tetrahydrofuran or dimethylsulfoxide in the presence of water at 0 ° C to 80 ° C.
  • an inert solvent such as tetrahydrofuran or dimethylsulfoxide
  • the propene derivative (V) used as a raw material in the production of the carbamate derivative () of the present invention can be produced by an ordinary method using readily available raw materials.
  • the representative examples are shown below.
  • the carbamate derivative of the present invention has excellent herbicidal activity against annual rice weeds such as Nobie which is a paddy weed; It also has herbicidal activity against perennial weeds. In addition, it has high selectivity and can effectively control these weeds at a dose of, for example, about 50 g per 10 ares, and does not cause harm to paddy rice at the above dose.
  • the herbicide of the present invention contains the above-mentioned carbamate derivative, that is, the novel carbamate derivative of the present invention represented by the general formula (III) as an active ingredient. It can be mixed with a solid carrier such as mineral fine powder and formulated into wettable powders, emulsions, powders, granules and the like. A surfactant may be added to impart emulsifiability, dispersibility, spreadability and the like during formulation.
  • the herbicide of the present invention When used in the form of a wettable powder, it is usually used in a proportion of 10 to 55% by weight of the carbamate derivative of the present invention, 4 ° to 88% by weight of the solid carrier and 2 to 5% by weight of the surfactant.
  • the composition may be prepared by blending on a table and used.
  • the emulsion When used in the form of an emulsion, it is usually compounded in a proportion of 20 to 50% by weight of the power bamate derivative of the present invention, 35 to 75% by weight of a solvent and 5 to 15% by weight of a surfactant.
  • L
  • the carbamate derivative of the present invention when used in the form of a powder, is usually blended at a ratio of 0.5 to 16% by weight, a solid carrier at 80 to 97.5% by weight, and a surfactant at a ratio of 2 to 5% by weight. It may be prepared by adjusting. Further, when used in the form of granules, the carbamate derivative of the present invention is in a ratio of 0.5 to 16% by weight, a solid carrier is 80 to 97.5% by weight, and a surfactant is 2 to 5% by weight. What is necessary is just to mix and prepare. Here, fine powder of a mineral substance is used as the solid carrier.
  • Examples of the fine powder of the mineral substance include oxides such as diatomaceous earth and slaked lime, phosphates such as apatite, sulfates such as Secco, talc and pie. Mouth ferrite, clay, violin, bentonite, acid clay, white carbon, quartz powder, gay stone powder and the like can be mentioned.
  • organic solvent power is used.
  • any of an anionic type, a nonionic type, a cationic type and a zwitterionic type (amino acid, betaine, etc.) can be used.
  • the herbicide of the present invention may contain other herbicidally active ingredients, if necessary, together with the carbamate derivative represented by the general formula (III) as an active ingredient.
  • other herbicidally active ingredients include known herbicides such as phenoxy, diphenyl ether, triazine, urea, carbamate, thiol carbamate, acid anilide, and pyrazole. , Phosphate, sulfonylprea, oxadiazone, etc., and can be used by appropriately selecting from these herbicides.
  • the herbicide of the present invention can be mixed with an insecticide, a fungicide, a plant growth regulator, a fertilizer, and the like, if necessary.
  • Methyl N— (3- ⁇ f-sopropenylbenzyl) carbamate 3.81 (18.6 mimol) was dissolved in 1,1,1-trichloro-2,2,2-trifluoroethane 14 Om 1 0.03 g of cuprous copper and 2.5 ml of piperidine (25.3 mmol) were sequentially added, and the mixture was heated under reflux for 1 hour. Next, 5% by weight of hydrochloric acid was added, and the mixture was extracted with chloroform. The extract was dried over anhydrous sodium sulfate.
  • 3-isopropenylbenzyl alcohol 0.60 g (4.0 mmol), potassium carbonate 1.lg (8.0 mmol), N, N-dimethylaminopyridine 0.02 g s 18-crown-6.
  • 02 g was dissolved in 25 ml of acetone, 1.0 ml (7.9 mmol) of N, N-ethylcarbamic acid chloride was added, and the mixture was refluxed for 20 hours. Next, water and a saturated aqueous solution of sodium carbonate were sequentially added and extracted with ether.
  • talc trade name: di-cryt
  • alkyl sulfonic acid salt trade name: neopellets, manufactured by Kao Atlas Co., Ltd.
  • nonionic type and anion Type surfactant trade name: Solbol 8 O0A, manufactured by Toho Chemical Industry Co., Ltd.
  • Paddy field soil was filled in a porcelain pot of 1/15500 are, and seeds of nobies, evening magallari, and broadleaf weeds (Kikasigusa, Konagi) were uniformly sown on the surface layer, and rice plants in the second leaf stage were transplanted.
  • Tables 9 (1) to (7) show the results of investigations on the herbicide effect and rice crop damage 20 days after chemical treatment.
  • the dose was expressed in terms of the amount of active ingredient per 1 are.
  • the phytotoxicity of rice and the herbicidal effect were measured by air-dry weight, and indicated as follows.
  • Test Example 1 Compound No. 2 50 550 Test Example 2 Compound No. 3 50 550 Test Example 3 Compound No. 9 50 550 Test Example 4 Compound No. 1 150 550 Test Example 5 Compound No. 14 50 55 0 Test Example 6 Compound No. 17 50 55 0 Test Example 7 Compound No. 22 50 55 0 Test Example 8 Compound No. 23 50 55 0 Test Example 9 Compound No. 25 50 55 0 Test example 10 Compound No. 27 5 ⁇ 550 Test example 11 Compound No. 35 50 55 0 Test example 12 Compound No. 36 50 55 0 Test example 13 Compound No. 37 50 55 0 Test example 14 Compound No. 41 50 55 0 Test example 15 Compound No. 42 50 55 1 Test example 16 Compound No.
  • Test Example 71 ⁇ ⁇ ⁇ 4 ⁇ l ⁇ . L ⁇ 7 50 5 5 5 0
  • Test Example 72 Compound No. 1 18 5 U 550
  • Test Example 73 73 ⁇ ⁇ 3 ⁇ 4 ⁇ ⁇ ⁇ . 95 5 5 5 5 ⁇
  • the compounds of the present invention are superior to the comparative compounds in the selectivity of the genus of paddy rice and Nobies, and are superior in remarkably low leaf volume. It exerts the effect of inhibiting the growth of nobies.
  • Test Examples 1 to 88 exhibit herbicidal effects on annual broadleaf weeds.
  • Test Examples 9, 10, 13, 16, 17, 19, 24, 25, 27, 28, 30, 31, 32, 34 to 41, 43, 45, 71, 81, 85 The degree of herbicidal effect of the compound used in 5 was 5.
  • the novel carbamate derivative of the present invention has excellent herbicidal activity against paddy weeds, and is excellent in selectivity, particularly, selectivity between paddy rice and Nobie.
  • weeds can be effectively removed from paddy field weeds at a low dose, and the dose does not cause harm to rice. Therefore, the carbamate derivative of the present invention is extremely useful as a rice herbicide.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

On décrit un dérivé de carbamate doté d'une ossature phényle et d'un groupe carbamate qui lui est lié par des atomes de carbone. Ce dérivé se révèle excellent pour tuer les herbes de basse altitude qu'il peut éliminer même à faible dose alors qu'il n'entraîne que des dégâts fort minimes pour le riz cultivé en paddy, ce qui en fait un excellent herbicide.
PCT/JP1993/001019 1992-07-27 1993-07-22 Derive de carbamate et herbicide le contenant comme ingredient actif WO1994002449A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AU45849/93A AU4584993A (en) 1992-07-27 1993-07-22 Carbamate derivative and weedkiller containing the same as active ingredient
KR1019950700320A KR950702526A (ko) 1992-07-27 1993-07-22 카바메이트 유도체 및 이것을 유효성분으로하는 제초제

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP4/200036 1992-07-27
JP20003692 1992-07-27

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WO1994002449A1 true WO1994002449A1 (fr) 1994-02-03

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PCT/JP1993/001019 WO1994002449A1 (fr) 1992-07-27 1993-07-22 Derive de carbamate et herbicide le contenant comme ingredient actif

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KR (1) KR950702526A (fr)
CN (1) CN1091124A (fr)
AU (1) AU4584993A (fr)
TW (1) TW234716B (fr)
WO (1) WO1994002449A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000020405A1 (fr) * 1998-10-07 2000-04-13 Mitsubishi Chemical Corporation Melanges d'isomeres optiques de 2,3-epoxypropanes disubstitues en 1,2, leur procede de production, pesticides les contenant sous forme de principe actif et intermediaire de ceux-ci

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
No relevant documents disclosed. *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000020405A1 (fr) * 1998-10-07 2000-04-13 Mitsubishi Chemical Corporation Melanges d'isomeres optiques de 2,3-epoxypropanes disubstitues en 1,2, leur procede de production, pesticides les contenant sous forme de principe actif et intermediaire de ceux-ci

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CN1091124A (zh) 1994-08-24
AU4584993A (en) 1994-02-14
KR950702526A (ko) 1995-07-29
TW234716B (fr) 1994-11-21

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