[go: up one dir, main page]

WO1996033994A1 - Derives amino-substitues, leur procede de preparation et herbicide - Google Patents

Derives amino-substitues, leur procede de preparation et herbicide Download PDF

Info

Publication number
WO1996033994A1
WO1996033994A1 PCT/JP1996/001155 JP9601155W WO9633994A1 WO 1996033994 A1 WO1996033994 A1 WO 1996033994A1 JP 9601155 W JP9601155 W JP 9601155W WO 9633994 A1 WO9633994 A1 WO 9633994A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
alkyl
optionally substituted
alkoxy
alkyl group
Prior art date
Application number
PCT/JP1996/001155
Other languages
English (en)
Japanese (ja)
Inventor
Akiyoshi Ueda
Yasuyuki Miyazawa
Daisuke Sato
Yoshihiko Hara
Masami Koguchi
Isoko Matsumoto
Takashi Kawana
Original Assignee
Nippon Soda Co., Ltd.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Nippon Soda Co., Ltd. filed Critical Nippon Soda Co., Ltd.
Publication of WO1996033994A1 publication Critical patent/WO1996033994A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • 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
    • A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
    • 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
    • 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
    • C07D413/12—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 chain containing hetero atoms as chain links
    • 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
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings

Definitions

  • the present invention relates to novel amino-substituted derivatives, production methods and herbicides.
  • Background art :
  • An object of the present invention is to provide a herbicide which can be synthesized industrially advantageously, is effective at a low dose, has high safety, and has high crop selectivity. Disclosure of the invention:
  • A represents N or CR 3
  • Z represents 0 or S
  • Q is a carbon atom benzene
  • R 2 each independently hydrogen atom, alkyl group, C, - 6 alkoxy groups, halo alkyl groups, halo C 6 alkoxy group, C, - 6 alkylamino amino group, di C DOO 6 alkylamino amino group, C alkylthio group, Represents a halogen atom or a cyano group
  • R 3 represents a hydrogen atom, a C alkyl group, a halogen atom, a nitro group, a formyl group, an acyl group, or may form a ring together with R 2
  • X is wherein NR 4 R 5 (wherein, R 4 and R 5 are each independently a hydrogen atom, alkyl
  • R 4 and R 5 may represent a group, an optionally substituted benzoyl group or an optionally substituted heterocyclic carbonyl group, or may form a ring together. However, R 4 and R 5 are not both ds alkoxycarbonyl groups. ).
  • examples of the heterocycle represented by Q include the following.
  • Upsilon, - 5 is hydrogen, C, - 6 alkyl group, C 3 - 7 cycloalkyl group, halo C
  • examples of the hetero ring formed by R 4 and R 5 together in the group represented by X include a hetero ring represented by the following formula.
  • C have alkyl groups, C 3 - 7 cycloalkyl, C, - 6 alkoxy 6 ⁇ alkyl group, C, - 6 alkylthio C, - 6 alkyl group, C, - Ji 6 alkylsulfonyl, -
  • R 7 represents a hydrogen atom, a C atom, an amino group or a carboxyl
  • Salts of the compound represented by the general formula [1] include deer horticulturally acceptable salts, for example, inorganic salts such as hydrochloride and hydrogen bromide, and organic salts such as acetate, oxalate and formate. Acid salts, etc., and alkali metals, alkaline earth metals, ammonium salts and the like.
  • the compound of the present invention can be produced by the following method.
  • the compound represented by the general formula [2] and the compound represented by the general formula [3] are coupled in an organic solvent in the presence of a suitable base.
  • Bases used in the reaction include metal hydrides such as hydrogenated sodium, carbonates such as carbonated carbon, and organic bases such as triethylamine.
  • the solvent used is DMF. , DMS O, THF, DME and the like. The reaction mixture is stirred at 0 to 90, and sometimes at 120, until the reaction is completed.
  • the 0-heterocyclic-substituted phenol derivative of the starting compound [3] in the above reaction is as follows. It can be manufactured by the method described below.
  • solvents used in the following reactions include alcohols such as methanol, ethanol, and isopropyl alcohol, aromatic hydrocarbons such as benzene and toluene, dichloromethane, and chloroform.
  • Halogenated hydrocarbons such as mouth form, ethers such as getyl ether and THF, ketones such as acetone and MEK, esters such as methyl acetate and ethyl acetate, and non-protons such as DMF and DMS 0 Polar solvents, nitriles such as acetate tritriol, and water.
  • the bases used include sodium carbonate, carbonates such as carbon dioxide, sodium hydroxide, metal hydroxides such as hydroxide, sodium methylate, sodium ethylate and the like.
  • Metal alcoholates such as sodium hydroxide, metal hydrides such as sodium hydride, alkyl metals such as butyllithium, lithium amides such as lithium diisopropylamide, lithium bistrimethylsilylamide, and triethylamido And organic bases such as DBU.
  • the acids used are mineral acids such as hydrochloric acid, nitric acid and sulfuric acid, organic acids such as formic acid and acetic acid, and Lewis acids such as aluminum chloride and boron trifluoride dimethyl ether. The reaction proceeds smoothly within the temperature range of the boiling point of the solvent used since —90.
  • X represents the same meaning as described above, L, represents an alkoxy group, a chlorine atom or a 1-imigzole group, and y, represents an alkyl group, a benzyl group or a p-toluenesulfonyl group.
  • ⁇ 3 is a compound of 1,2.4_triazole-3-yl
  • the compound [7] can be produced by reacting the compound [7] with acid chloride or acid anhydride in DMF at 0 to 120 ° C.
  • X represents the same meaning as described above, and y 2 represents an alkyl group, an aryl group, or a haloalkyl group.
  • 2-substituted — 1, 2, 4 — triazol-3-yl derivatives are prepared according to the method described in J. Org. Chem. 44, vol. 4, page 4160 (1977).
  • the amide [8] is reacted with dimethylformamide dimethyl acetal to synthesize N—C (dimethylamino) methylene] amide [9].
  • [9] is reacted with hydrazines to induce triazole [10].
  • L 2 is a methoxymethoxy or benzyloxy group, it can be obtained by treating [10] with an acid or by a hydrocracking reaction using palladium carbon or the like as a catalyst.
  • L 2 represents a methoxymethoxy group, a benzyloxy group, a nitro group, or a halogen atom
  • L 3 represents an alkyl group or a benzyl group
  • y 3 represents an alkyl group. Represents a benzyl group or a phenyl group.
  • X, L 2 , L 3 and y 5 represent the same meaning as described above, and ys represents an alkyl group, an aryl amino group, an alkyl amino group or an aryl amino group.
  • a derivative in which Q is thiazol-5-yl can also be produced by the same method as described above.
  • L 4 represents a halogen
  • y l 0 represents hydrogen, methyl, Echiru group or alkyl carbonylation Le group
  • y is hydrogen Represents an atom, alkyl group or funinyl group.
  • y 12 represents an alkyl group or a phenyl group
  • y 13 represents a hydrogen atom, an alkyl group, a benzyl group.
  • Ki Hue Represents a nyl group, an alkoxycarbonyl group or a tosyl group, represents a hydrogen atom, an alkyl group or a benzyl group.
  • y 15 represents a hydrogen atom, an alkyl group or a halogen atom.
  • a mixture of the isoxazolin-3-yl and the isoxazolin-5-yl forms can be easily separated by mouth chromatography or recrystallization.
  • y 16 represents a hydrogen atom, an alkyl group or a phenyl group.
  • it can be obtained by reacting benzofuran and hydroxylamine with alcohol at 25 to 80 for 0.5 to 8 hours. Can be done.
  • y 17 is a hydrogen atom, an alkyl group, a benzyl group, an aryl group, a haloalkyl group.
  • An alkoxyalkyl group or an alkylthioalkyl group is represented by X, L,, L 2 or L represents the same meaning as described above.
  • y 18 and y l 9 is Shiano group, an alkoxycarbonyl group, or to display the Fuweniru group, X and L 2 are as defined above.
  • L 4 represents a halogen atom, preferably fluorine
  • the compound of the formula [65] can be produced by a method similar to the above-mentioned phenol derivative synthesis method, by reacting a compound of the general formula [66] with sodium sulfide, thiourea or the like.
  • [65] can also be produced by applying the aniline derivative [69] to the method described in Organic Synthesis Color 1 ect., Vol. 3, page 809. (In the formula, L 4 represents halogen.)
  • the compound of the present invention can also be produced by the following method. 96/33994
  • this is a method for producing [1] by reacting the compound represented by the general formula [55] with an appropriate condensing agent shown in the production method of the above [3].
  • the compound represented by the general formula [56] and sodium azide are placed in a suitable solvent, preferably using DMF, at room temperature to a temperature not higher than the boiling point of the solvent, preferably 80 to 120. It is produced by reacting for 1-2 hours.
  • the solvent used in this reaction include alcohols such as methanol, ethanol and isopropanol, aromatic hydrocarbons such as benzene and toluene, and halogenated carbons such as dichloromethane and chloroform.
  • the compound represented by the general formula [59] is reacted with TosMIC in a suitable solvent in a suitable solvent at a temperature from room temperature to a temperature lower than the boiling point of the solvent for 1 to 24 hours according to a method known in the literature. It is manufactured by
  • the compound of the formula [60] and hydrazines are reacted in the presence or absence of a suitable base in a suitable solvent at a temperature from room temperature to a temperature lower than the boiling point of the solvent for 1 to 24 hours. It is produced by reacting.
  • Solvents used in this reaction include, for example, alcohols such as methanol, ethanol, and isopropanol; aromatic hydrocarbons such as benzene and toluene; dichloromethane; Halogenated hydrocarbons, ethers such as getyl ether and THF, ketones such as acetone and MEK, esters such as methyl acetate and ethyl acetate, and non-protonic polar solvents such as DMF and DMSO , Acetonitrile, water and the like.
  • Examples of the base used in this reaction include carbonates such as sodium carbonate and carbonated carbonate, metal hydroxides such as sodium hydroxide and potassium hydroxide, and sodium hydroxide.
  • the compound represented by the general formula [61] and the promoter [15] are reacted with a suitable base in the presence or absence of a suitable base in a suitable solvent at a temperature from room temperature to a temperature lower than the boiling point of the solvent. Manufactured by reacting for 4 hours.
  • the solvent used for this reaction include methanol, ethanol, and isoprono.
  • Alcohols such as ethanol, aromatic hydrocarbons such as benzene and toluene, halogenated hydrocarbons such as dichloromethane and chloroform, ethers such as getyl ether and THF, and ketones such as acetate and MEK.
  • the aldehyde represented by the general formula [62] and isonitrile [37] are compared to the aldehyde in the presence of a suitable base of at least 2 S in a suitable solvent at room temperature to below the boiling point of the solvent. It is produced by reacting at a temperature of 1 to 24 hours.
  • the solvent used in this reaction include alcohols such as methanol, ethanol and isopropanol, aromatic hydrocarbons such as benzene and toluene, halogenated hydrocarbons such as dichloromethane and chloroform, and getyl.
  • Ethers such as ether and THF; non-protonic polar solvents such as DMF and DMS 0; and acetonitrile.
  • Examples of the base used in this reaction include carbonates such as sodium carbonate and potassium carbonate, metal hydroxides such as sodium hydroxide and hydroxylating water, and sodium methylate.
  • Metal alcohols such as sodium and sodium ethyl ethers; metal hydrides such as sodium hydride and potassium hydride; lithium amides such as lithium diisopropyl amide and lithium p-methylsilyl amide; And organic bases such as DBU.
  • [1j] is produced by reacting for 2 hours.
  • the solvent used for this reaction include methanol, ethanol, and isoprono.
  • Alcohols such as ethanol, aromatic hydrocarbons such as benzene and toluene, halogenated hydrocarbons such as dichloromethane and chloroform, ethers such as getyl ether and THF, and non-hydrocarbons such as DMF and DMS0.
  • Examples include protonic polar solvents and acetonitril.
  • the base used in this reaction include carbonates such as sodium carbonate and carbonated carbonate, metal hydroxides such as sodium hydroxide and hydroxylated phosphate, and sodium hydride.
  • metal hydrides such as tritium and potassium hydride, lithium amides such as lithium diisopropyl amide and lithium bistrimethylsilyl amide, and organic bases such as triethylamine and DBU.
  • the acylimidazole represented by the general formula [63] and the amide oxime [47] are reacted in a suitable solvent in the presence of a suitable base at a temperature of 115 to 140 for 1 to 24 hours.
  • the reaction produces [lk].
  • the solvent used in this reaction include aromatic hydrocarbons such as benzene and toluene; halogenated hydrocarbons such as dichloromethane and chloroform; ethers such as getyl ether and THF; Non-protonic polar solvents such as F and DMSO, acetonitrile, and the like.
  • Bases used in this reaction include carbonates such as sodium carbonate and carbonated carbonate, metal hydroxides such as sodium hydroxide and hydroxylated phosphate, and sodium hydride.
  • Metal hydrides such as potassium and potassium hydride; lithium amides such as lithium diisopropylamide; and organic bases such as triethylamine and DBU.
  • the compound represented by the general formula [] can be prepared by a method known in the literature, in the presence of a suitable base or acid, without a solvent or in a suitable solvent, at a temperature lower than the boiling point of the solvent.
  • Z 2 represents oxygen or sulfur
  • y 22 represents alkyl or aryl
  • yl 4 has the same meaning as described above.
  • reaction of the compound of the general formula [1j] with [64] in the presence of a suitable base in a suitable solvent at a temperature of ⁇ 15 to 25 ° C. for 1 to 24 hours yields [11 1 ] Is manufactured.
  • solvent used in this reaction include alcohols such as methanol, ethanol, and isopropanol; aromatic hydrocarbons such as benzene and toluene; halogenated hydrocarbons such as dichloromethane and chloroform; Ethers such as tyl ether and THF; ketones such as acetone and MEK; esters such as methyl acetate and ethyl acetate; non-protonic polar solvents such as DMF and DMS 0; Water and the like.
  • Examples of the base used in this reaction include carbonates such as sodium carbonate and potassium carbonate, gold hydroxides such as sodium hydroxide and potassium hydroxide, sodium methylate, and the like.
  • Metal alcohols such as sodium ethylate; metal hydrides such as sodium hydride and potassium hydride; lithium diisopropyl Examples thereof include lithium amides such as amide and lithium bistrimethylsilyl amide, and organic bases such as triethylamine and DBU.
  • a compound of the general formula [70] (wherein R,, R 2 , A and Z represent the same meaning as described above); and a compound of the general formula [66] (wherein Q, X, Y n, L, have the same meaning as described above.))
  • the compound is coupled in an organic solvent in the presence of a base.
  • the base include metal hydrides such as hydrogenated sodium, carbonates such as carbonated lime, and organic bases such as triethylamine.
  • the solvent include DMF, DMS O, and THF. , DME and the like.
  • the reaction mixture is stirred at 0-90 ° C., possibly at 120 ° C., until the reaction is complete.
  • the structure of the compound of the present invention was determined from IR, NMR, MS and the like.
  • n n H H 0 H H H 3H0 3H0 1 0 LZ-Z n u n u
  • HHHH 0 H 3W0 9H0 1 0 9S-Z unnu HHUHH a H0 3 0 I 0
  • OW 1300D-H3 HD H H 3W0 awo 8 ⁇ - ⁇ ⁇ 3 ⁇ 43
  • N3-HD HD H H 3W0 awo
  • the compound of the present invention shows high herbicidal activity under soil cultivation conditions in both soil treatment and foliage treatment, and various compounds such as Aquinoeno korogusa, Ichibi and Inubu, etc. It is effective for field weeds and contains compounds that are selective for crops such as corn, wheat, soybeans, and potatoes.
  • the compound of the present invention also includes a compound that is useful for producing growth suppression for useful plants such as crops, ornamental plants, and fruit trees.
  • the compound of the present invention has excellent herbicidal activity against various paddy weeds such as nobie, evening magayalli, omomodaka and hoyurui, and shows selectivity to rice.
  • the compound of the present invention can be applied to the control of weeds in orchards, lawns, track ends, vacant lots and the like.
  • the compounds of the present invention include those having a plant growth regulating action, and the intermediate compounds of the present compounds also include those having a herbicidal activity.
  • the herbicide of the present invention contains one or more of the compounds of the present invention as an active ingredient.
  • a general pesticide for the purpose of using it as a pesticide that is, a wettable powder, an abductant, a powder, It can also be used in the form of emulsions, aqueous solvents, suspensions, flowables and the like.
  • vegetable powders such as soybean flour and flour, diatomaceous earth, apatite, gypsum, talc, bentonite, pyrophyllite, clay and other mineral fine powders
  • Organic and inorganic compounds such as sodium benzoate, urea, and sodium sulfate are used.
  • petroleum fractions such as kerosene, xylene and sorbent naphtha, cyclohexane, cyclohexanone, dimethylformamide, dimethylsulfoxide, alcohol, acetate, and tris
  • chlorethylene, methylisobutyl ketone, mineral oil, vegetable oil, water, etc. as solvents.
  • a surfactant may be added if necessary.
  • the concentration of the active ingredient in the herbicide of the present invention varies depending on the form of the preparation described above. 5 to 90%, preferably 10 to 85% for wettable powders; 3 to 70%, preferably 5 to 30% for emulsions. %: For abductants, a concentration of 0.01 to 30%, preferably 0.05 to 10% is used.
  • the wettable powder and emulsion thus obtained are diluted with water to a predetermined degree to form a suspension or an emulsion, and the granules are directly sprayed on the soil before or after germination of the weeds. Or mixed. In actually applying the herbicide of the present invention, an appropriate amount of 0.1 g or more of the active ingredient is applied per 10 ares.
  • the herbicide of the present invention can be used in combination with known fungicides, insecticides, acaricides, herbicides, plant growth regulators and the like.
  • the synergistic action of the mixed drug can be expected to have a much higher effect. In that case, a combination with a plurality of known herbicides is also possible.
  • Suitable agents to be used in combination with the herbicide of the present invention include carbamate herbicides such as benthiocarb, molinate, and dimepirate, acid carbohydrate herbicides, butachlor, pretilachlor, and mefenacet. Mid-type herbicides, diphenyl ether-type herbicides such as chrometoxynil, biphenox, etc .; triazine-type herbicides such as atrazine and cyanadine; and sulfonyl-urea-type herbicides such as chlorsulfuron and sulfometurone monomethyl.
  • carbamate herbicides such as benthiocarb, molinate, and dimepirate, acid carbohydrate herbicides, butachlor, pretilachlor, and mefenacet.
  • Mid-type herbicides diphenyl ether-type herbicides such as chrometoxynil, biphenox, etc .
  • triazine-type herbicides such
  • Carboxylic acid herbicides such as MCP, MCPB, etc., phenoxycarboxylic acid herbicides such as diclohop-methyl, etc., and pyridyloxyphenoxypropionic acid such as fludihopbutyl.
  • Dinitroaniline such as herbicides, trifluralin, and pendimethalin Herbicides, urea herbicides such as linuron and diuron, benzoylaminopropionic acid herbicides such as benzoylprophetyl and flavonopetyl, and imidazolinone herbicides such as imazaquin; and others, biverofos , Daimron, Benzozon, Difenzocoat, Nabroanilide, Etobenzanide, Triazophenamide, Kink Mouth Rack, and Xanthion herbicides such as Sethoxydim, Cresodim, etc.
  • Example 3 wettable powder
  • the above components were uniformly mixed and finely pulverized to obtain a wettable powder containing 20% of the active ingredient.
  • the above mixture was uniformly mixed and finely pulverized, and then granulated into particles having a diameter of 0.5 to 10 mm to obtain granules having an active ingredient of 5%.
  • T of the following test examples on the effect of the present invention herbicides The herbicidal effect was investigated according to the following criteria and expressed as a herbicidal index ⁇
  • the numbers 1, 3, 5, 7, and 9 are intermediate values between 0 and 2, 2 and 4, 4 and 6, 6, 8 and 10 respectively.
  • Table 11 1 Compound No.Dose Noviet Tamagayarimodoka transplanted rice g / ha
  • the paddy of the present invention shows high herbicidal activity in any of soil treatment and foliage treatment under upland cropping conditions, and is effective against various field weeds such as Aquinoeno korogusa, Ichibi and Inubu.
  • the compounds of the present invention also include compounds that exhibit a growth-inhibiting effect on useful plants such as crops, ornamental plants, and fruit trees.
  • the compound of the present invention has an excellent herbicidal activity against various paddy weeds such as Nobie, Tamagayari, Omodaka, Hoyurui, etc., and contains fossils showing selectivity to rice. .
  • the compound of the present invention can also be applied to the control of weeds in orchards, lawns, roadsides, vacant lots and the like.
  • composition containing the compound of the present invention is useful as a herbicide.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

La présente invention concerne de nouveaux dérivés amino-substitués représentés par la formule générale (I), qui présentent une activité herbicide supérieure à celle de produits analogues connus; elle concerne aussi un procédé de préparation de ces dérivés et un herbicide comprenant ces substances en tant que principe actif. Dans ladite formule, A étant N ou CR3, Z étant O ou S, Q étant un hétérocycle pentagonal ou hexagonal, R1 et R2 étant chacun, de façon indépendante, H, alkyle C1-C6, alcoxy C1-C6 ou analogue, R3 étant H, alkyle C1-C6, halogéno ou analogue, et X étant NR4R5 (R4 et R5 étant chacun, de façon indépendante, H, alkyle C1-C6, cycloalkyle C3-C7, alcoxy C1-C6, alkyle C1-C6 ou analogue, ou bien R4 et R5 peuvent former ensemble un anneau.
PCT/JP1996/001155 1995-04-28 1996-04-26 Derives amino-substitues, leur procede de preparation et herbicide WO1996033994A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP7/129334 1995-04-28
JP12933495 1995-04-28

Publications (1)

Publication Number Publication Date
WO1996033994A1 true WO1996033994A1 (fr) 1996-10-31

Family

ID=15007043

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP1996/001155 WO1996033994A1 (fr) 1995-04-28 1996-04-26 Derives amino-substitues, leur procede de preparation et herbicide

Country Status (1)

Country Link
WO (1) WO1996033994A1 (fr)

Cited By (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004065380A1 (fr) * 2003-01-14 2004-08-05 Arena Pharmaceuticals Inc. Derives aryles et heteroaryles tri-substitues en position 1,2,3 en tant que modulateurs de metabolisme et prophylaxie et traitement de troubles lies au metabolisme
EP1927594A1 (fr) * 2003-01-14 2008-06-04 Arena Pharmaceuticals, Inc. Dérivés d'aryle et d'hétéroaryle 1,2,3-trisubstitués en tant que modulateurs du métabolisme et la prévention et le traitement de maladies liées à celui-ci, telles que le diabète et l'hyperglycémie
US7470715B2 (en) 2005-12-22 2008-12-30 Pfizer Inc. Estrogen modulators
US7470699B2 (en) 2003-07-11 2008-12-30 Arena Pharmaceuticals, Inc. Trisubstituted aryl and heteroaryl derivatives as modulators of metabolism and the prophylaxis and treatment of disorders related thereto
US7812025B2 (en) 2005-08-12 2010-10-12 Takeda Pharmaceutical Company Limited Brain/neuronal cell-protecting agent and therapeutic agent for sleep disorder
CN1835943B (zh) * 2003-01-14 2012-03-07 阿伦纳药品公司 作为代谢调节剂的1，2，3-三取代的芳基和杂芳基衍生物及其应用
US8969347B2 (en) 2008-06-03 2015-03-03 Intermune, Inc. Compounds and methods for treating inflammatory and fibrotic disorders
US9221756B2 (en) 2011-12-05 2015-12-29 University Of Leicester Pyrrole derivatives
US9359379B2 (en) 2012-10-02 2016-06-07 Intermune, Inc. Anti-fibrotic pyridinones
US9527816B2 (en) 2005-05-10 2016-12-27 Intermune, Inc. Method of modulating stress-activated protein kinase system
US9561231B2 (en) 2012-06-12 2017-02-07 Abbvie Inc. Pyridinone and pyridazinone derivatives
US9695155B2 (en) 2013-12-10 2017-07-04 E I Du Pont De Nemours And Company Herbicidal substituted pyrimidinyloxy benzene compounds
US10131652B2 (en) 2014-01-16 2018-11-20 E. I. Du Pont De Nemours And Company Pyrimidinyloxy benzene derivatives as herbicides
US10233195B2 (en) 2014-04-02 2019-03-19 Intermune, Inc. Anti-fibrotic pyridinones
US10485235B2 (en) 2015-07-13 2019-11-26 Fmc Corporation Aryloxypyrimidinyl ethers as herbicides
US10894787B2 (en) 2010-09-22 2021-01-19 Arena Pharmaceuticals, Inc. Modulators of the GPR119 receptor and the treatment of disorders related thereto
US11007175B2 (en) 2015-01-06 2021-05-18 Arena Pharmaceuticals, Inc. Methods of treating conditions related to the S1P1 receptor
US11006631B2 (en) 2015-03-18 2021-05-18 Fmc Corporation Substituted pyrimidinyloxy pyridine derivatives as herbicides
US11053204B2 (en) 2015-06-05 2021-07-06 Fmc Corporation Pyrimidinyloxy benzene derivatives as herbicides
US11427549B2 (en) 2017-05-02 2022-08-30 Fmc Corporation Pyrimidinyloxy benzo-fused compounds as herbicides
WO2023186690A1 (fr) * 2022-03-28 2023-10-05 Bayer Aktiengesellschaft 2-aminoazines substituées et leurs sels, et leur utilisation comme principes actifs herbicides
US11884626B2 (en) 2015-06-22 2024-01-30 Arena Pharmaceuticals, Inc. Crystalline L-arginine salt of (R)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclo-penta [b]indol-3-yl)acetic acid(Compound1) for use in S1P1 receptor-associated disorders
US12156866B2 (en) 2018-06-06 2024-12-03 Arena Pharmaceuticals, Inc. Methods of treating conditions related to the S1P1 receptor

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH04342586A (ja) * 1991-04-17 1992-11-30 Ishihara Sangyo Kaisha Ltd アジン系化合物、それらの製造方法及びそれらを含有する除草剤
JPH05202038A (ja) * 1992-01-30 1993-08-10 Sumitomo Chem Co Ltd アゾール誘導体、その製造法およびそれを有効成分とする除草剤
WO1994017059A1 (fr) * 1993-01-29 1994-08-04 Nippon Soda Co., Ltd. Derive heterocyclique
WO1996004278A1 (fr) * 1994-08-02 1996-02-15 Nippon Soda Co., Ltd. Derive d'oxazole, son procede de production et herbicide

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH04342586A (ja) * 1991-04-17 1992-11-30 Ishihara Sangyo Kaisha Ltd アジン系化合物、それらの製造方法及びそれらを含有する除草剤
JPH05202038A (ja) * 1992-01-30 1993-08-10 Sumitomo Chem Co Ltd アゾール誘導体、その製造法およびそれを有効成分とする除草剤
WO1994017059A1 (fr) * 1993-01-29 1994-08-04 Nippon Soda Co., Ltd. Derive heterocyclique
WO1996004278A1 (fr) * 1994-08-02 1996-02-15 Nippon Soda Co., Ltd. Derive d'oxazole, son procede de production et herbicide

Cited By (42)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8933083B2 (en) 2003-01-14 2015-01-13 Arena Pharmaceuticals, Inc. 1,2,3-trisubstituted aryl and heteroaryl derivatives as modulators of metabolism and the prophylaxis and treatment of disorders related thereto such as diabetes and hyperglycemia
EP1927594A1 (fr) * 2003-01-14 2008-06-04 Arena Pharmaceuticals, Inc. Dérivés d'aryle et d'hétéroaryle 1,2,3-trisubstitués en tant que modulateurs du métabolisme et la prévention et le traitement de maladies liées à celui-ci, telles que le diabète et l'hyperglycémie
HRP20050696B1 (en) * 2003-01-14 2008-10-31 Arena Pharmaceuticals Inc. 1,2,3-trisubstituted aryl and heteroaryl derivatives as modulators of metabolism and the prpphylaxis and treatment of disorders related thereto such as diabetes and hyperglycemia
EA011009B1 (ru) * 2003-01-14 2008-12-30 Арена Фармасьютикалз Инк. 1,2,3-тризамещённые арильные и гетероарильные производные в качестве модуляторов метаболизма и профилактика и лечение расстройств, связанных с ним, таких как диабет и гипергликемия
WO2004065380A1 (fr) * 2003-01-14 2004-08-05 Arena Pharmaceuticals Inc. Derives aryles et heteroaryles tri-substitues en position 1,2,3 en tant que modulateurs de metabolisme et prophylaxie et traitement de troubles lies au metabolisme
AU2004205642B2 (en) * 2003-01-14 2011-01-27 Arena Pharmaceuticals, Inc. 1,2,3-trisubstituted aryl and heteroaryl derivatives as modulators of metabolism and the prophylaxis and treatment of disorders related thereto such as diabetes and hyperglycemia
AU2004205642C1 (en) * 2003-01-14 2012-01-12 Arena Pharmaceuticals, Inc. 1,2,3-trisubstituted aryl and heteroaryl derivatives as modulators of metabolism and the prophylaxis and treatment of disorders related thereto such as diabetes and hyperglycemia
CN1835943B (zh) * 2003-01-14 2012-03-07 阿伦纳药品公司 作为代谢调节剂的1，2，3-三取代的芳基和杂芳基衍生物及其应用
US8293751B2 (en) 2003-01-14 2012-10-23 Arena Pharmaceuticals, Inc. 1,2,3-trisubstituted aryl and heteroaryl derivatives as modulators of metabolism and the prophylaxis and treatment of disorders related thereto such as diabetes and hyperglycemia
US7470699B2 (en) 2003-07-11 2008-12-30 Arena Pharmaceuticals, Inc. Trisubstituted aryl and heteroaryl derivatives as modulators of metabolism and the prophylaxis and treatment of disorders related thereto
US9527816B2 (en) 2005-05-10 2016-12-27 Intermune, Inc. Method of modulating stress-activated protein kinase system
US10010536B2 (en) 2005-05-10 2018-07-03 Intermune, Inc. Method of modulating stress-activated protein kinase system
EP1923388A4 (fr) * 2005-08-12 2011-03-09 Takeda Pharmaceutical Agent protegeant des cellules du cerveau/neuronales et agent therapeutique pour des troubles du sommeil
US7812025B2 (en) 2005-08-12 2010-10-12 Takeda Pharmaceutical Company Limited Brain/neuronal cell-protecting agent and therapeutic agent for sleep disorder
US7470715B2 (en) 2005-12-22 2008-12-30 Pfizer Inc. Estrogen modulators
US8969347B2 (en) 2008-06-03 2015-03-03 Intermune, Inc. Compounds and methods for treating inflammatory and fibrotic disorders
US9290450B2 (en) 2008-06-03 2016-03-22 Intermune, Inc. Compounds and methods for treating inflammatory and fibrotic disorders
USRE47142E1 (en) 2008-06-03 2018-11-27 Intermune, Inc. Compounds and methods for treating inflammatory and fibrotic disorders
US10894787B2 (en) 2010-09-22 2021-01-19 Arena Pharmaceuticals, Inc. Modulators of the GPR119 receptor and the treatment of disorders related thereto
US9221756B2 (en) 2011-12-05 2015-12-29 University Of Leicester Pyrrole derivatives
US9561231B2 (en) 2012-06-12 2017-02-07 Abbvie Inc. Pyridinone and pyridazinone derivatives
US10376497B2 (en) 2012-10-02 2019-08-13 Intermune, Inc. Anti-fibrotic pyridinones
US10898474B2 (en) 2012-10-02 2021-01-26 Intermune, Inc. Anti-fibrotic pyridinones
US9359379B2 (en) 2012-10-02 2016-06-07 Intermune, Inc. Anti-fibrotic pyridinones
US9675593B2 (en) 2012-10-02 2017-06-13 Intermune, Inc. Anti-fibrotic pyridinones
US9695155B2 (en) 2013-12-10 2017-07-04 E I Du Pont De Nemours And Company Herbicidal substituted pyrimidinyloxy benzene compounds
US10654840B2 (en) 2014-01-16 2020-05-19 Fmc Corporation Pyrimidinyloxy benzene derivatives as herbicides
US11447476B2 (en) 2014-01-16 2022-09-20 Fmc Corporation Pyrimidinyloxy benzene derivatives as herbicides
EP3094631B1 (fr) 2014-01-16 2019-01-09 FMC Corporation Dérivés de pyrimidinyloxy benzène à utiliser en tant qu'herbicides
US10131652B2 (en) 2014-01-16 2018-11-20 E. I. Du Pont De Nemours And Company Pyrimidinyloxy benzene derivatives as herbicides
EP3094631B2 (fr) † 2014-01-16 2024-12-25 FMC Corporation Dérivés de pyrimidinyloxy benzène à utiliser en tant qu'herbicides
AU2019226283B2 (en) * 2014-01-16 2021-07-01 Fmc Corporation Pyrimidinyloxy benzene derivatives as herbicides
US10544161B2 (en) 2014-04-02 2020-01-28 Intermune, Inc. Anti-fibrotic pyridinones
US10233195B2 (en) 2014-04-02 2019-03-19 Intermune, Inc. Anti-fibrotic pyridinones
US11007175B2 (en) 2015-01-06 2021-05-18 Arena Pharmaceuticals, Inc. Methods of treating conditions related to the S1P1 receptor
US11006631B2 (en) 2015-03-18 2021-05-18 Fmc Corporation Substituted pyrimidinyloxy pyridine derivatives as herbicides
US11053204B2 (en) 2015-06-05 2021-07-06 Fmc Corporation Pyrimidinyloxy benzene derivatives as herbicides
US11884626B2 (en) 2015-06-22 2024-01-30 Arena Pharmaceuticals, Inc. Crystalline L-arginine salt of (R)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclo-penta [b]indol-3-yl)acetic acid(Compound1) for use in S1P1 receptor-associated disorders
US10485235B2 (en) 2015-07-13 2019-11-26 Fmc Corporation Aryloxypyrimidinyl ethers as herbicides
US11427549B2 (en) 2017-05-02 2022-08-30 Fmc Corporation Pyrimidinyloxy benzo-fused compounds as herbicides
US12156866B2 (en) 2018-06-06 2024-12-03 Arena Pharmaceuticals, Inc. Methods of treating conditions related to the S1P1 receptor
WO2023186690A1 (fr) * 2022-03-28 2023-10-05 Bayer Aktiengesellschaft 2-aminoazines substituées et leurs sels, et leur utilisation comme principes actifs herbicides

Similar Documents

Publication Publication Date Title
WO1996033994A1 (fr) Derives amino-substitues, leur procede de preparation et herbicide
JP4430938B2 (ja) 新規置換ピラゾール誘導体、その製造方法およびそれらを含有する除草剤組成物
JPH01121287A (ja) イミダゾリン類及び殺虫剤
FR2483406A1 (fr) Composes 3-isoxazolidinones, leur procede de preparation et compositions herbicides les contenant
JP2003064059A (ja) ピリミジン化合物、製造方法および除草剤
EP0332133B1 (fr) Dérivés du triazole, procédé pour leur préparation et compositions herbicides les contenant
JPH0372460A (ja) ３一置換フェニルピラゾール誘導体又はその塩類及び除草剤
JP2946656B2 (ja) ウラシル誘導体および除草剤
EP0197495B1 (fr) Dérivés de 4,5,6,7-tétrahydro-2H-indazole et herbicides les contenant
BE897301A (fr) Derives du n-phenylpoyrazole herbicides
EP0354766A2 (fr) Dérivés de 2,4-diphénylpyrimidine 5-substitués, leur production et utilisation comme herbicide
EP0655444B1 (fr) Oxazolines, procédé pour les préparer et compositions agricoles et horticoles pour le contrÔle des organismes nuisibles les contenant
JPH05320088A (ja) インダン−１，３−ジオン誘導体およびこれを有効成分とする除草剤
JPH02233602A (ja) 除草剤
JPH0739397B2 (ja) ピリダジノン誘導体および害虫防除剤
JPH0253775A (ja) ピラゾールカルボキサミド誘導体及び除草剤
JPH05208975A (ja) テトラヒドロフラン誘導体およびこれを有効成分とする除草剤
JPH08198855A (ja) ピリダジノン誘導体および害虫防除剤
JPH021484A (ja) ５，６―ジヒドロ―１，４，２―ジオキサジン誘導体および農園芸用殺菌剤
JPH0649041A (ja) カルバモイルトリアゾール誘導体、それを有効成分とする除草剤およびその製造方法
JPH0665239A (ja) ２−アシルアミノ−２−チアゾリン化合物、その製法及び有害生物防除剤
JPH02726A (ja) シクロヘキセノン誘導体、その製造方法及び除草剤
JPH07118242A (ja) フェノキシアルキルアミン誘導体、その製法及び農園芸用の有害生物防除剤
JP2005015421A (ja) ｏ−置換ベンゾイル化合物及びこれを有効成分とする除草剤
JPH05279356A (ja) Ｎ−ビニルイミダゾリジン誘導体、その製造法、それを有効成分として含有する殺虫剤および中間体

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): BR CN JP KR US

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH DE DK ES FI FR GB GR IE IT LU MC NL PT SE

121 Ep: the epo has been informed by wipo that ep was designated in this application
122 Ep: pct application non-entry in european phase