+

WO1994007857A1 - Compose amide cyclique et herbicide - Google Patents

Compose amide cyclique et herbicide Download PDF

Info

Publication number
WO1994007857A1
WO1994007857A1 PCT/JP1993/001406 JP9301406W WO9407857A1 WO 1994007857 A1 WO1994007857 A1 WO 1994007857A1 JP 9301406 W JP9301406 W JP 9301406W WO 9407857 A1 WO9407857 A1 WO 9407857A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
amide compound
key
cyclic amide
compound according
Prior art date
Application number
PCT/JP1993/001406
Other languages
English (en)
Japanese (ja)
Inventor
Yasuo Kawamura
Eiichi Oya
Kaoru Itoh
Hiroshi Kita
Hisashi Nakata
Kanji Sawada
Jun Satow
Tsutomu Nawamaki
Shigeomi Watanabe
Kimihiro Ishikawa
Yoichi Ito
Original Assignee
Nissan Chemical Industries, 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 Nissan Chemical Industries, Ltd. filed Critical Nissan Chemical Industries, Ltd.
Priority to AU48346/93A priority Critical patent/AU4834693A/en
Publication of WO1994007857A1 publication Critical patent/WO1994007857A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • 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
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members 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
    • C07D207/36—Oxygen or sulfur atoms
    • C07D207/38—2-Pyrrolones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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, directly attached to ring carbon atoms
    • C07D211/74—Oxygen atoms
    • C07D211/76—Oxygen atoms attached in position 2 or 6
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond

Definitions

  • the present invention relates to a novel cyclic amide compound and a selective herbicide containing the compound as an active ingredient.
  • the present inventors have shown selectivity for important crops, have an excellent herbicidal effect at a low drug dose on many weeds, and As a result of continuing research to develop a herbicide having a foliage treatment effect, the formula (111A) or the formula (111B)
  • R 1 , R L and R ⁇ each independently represent a hydrogen atom or a ⁇ c 4 alkyl group
  • X represents an oxygen atom or a sulfur atom
  • ⁇ c 4 a Ruki group a C ⁇ ⁇ C a Le co key sheet group CC Nono b a Noreki Le group or the C i ⁇ c 4 c b a Le co key sheet group
  • m represents an integer from 0 to 5, and if m is an integer from 2 to 5, Y may be the same or different.
  • n 1 or 2
  • Q represents an optionally substituted heterocyclic ring, an optionally substituted naphthalene ring, or an optionally substituted It was condensed heterocyclic shea ⁇ cyano group or C 0 2 A
  • A is a hydrogen atom, CC ⁇ A
  • Le key Le represents one group or a phenyl group.
  • Q ′ is an optionally substituted phenyl ring, an optionally substituted heterocyclic ring, an optionally substituted naphthalene ring, I substituted contracted if heterocycle, (the a represents. the same as defined above) C 0 2 a was or shea ⁇ cyano group represents a.
  • the compound of the present invention represented by the following formula:
  • R 1 represents a hydrogen atom, a methyl group, an ethyl group, or n-propyl
  • R 2 is a hydrogen atom, a methyl group, an ethyl group, n—propyl group, is 0—propyl group, n—butyl group, is 0—butyl Group, sec-butyl and tert-butyl groups, preferably hydrogen atoms, methyl and ethyl groups, and so on. More preferably, a methyl group and an ethyl group are provided.
  • R 3 is a hydrogen atom, a methyl group, an ethyl group, n—propyl group, iso—propyl group, n—butyl group, iso—butyl group, sec Both butyl and terbutyl groups are exposed and are preferred. Or a hydrogen atom, a methyl group or an ethyl group.
  • Y is a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a methyl group, an ethyl group, n-propyl group, iso-propyl group, n-petit atom Butyl, iso—butyl, sec—butyl, tert—butyl, methoxy, ethoxy, n—propoxy, iso—propo Xyl group, n — butoxy group, iso — butoxy group, sec — butoxy group, tert — butoxy group, difluoromethyl group, triphenyl Olemethyl group, chloromethyl group, bromomethyl group Pentafluoro group, 2 — chloromethyl group, difluoro group Toxi group, Trif ole oxime group, 2, 2, 2 — Trifluoro mouth ethoxy group, 2 — Cyclo mouth ethoxy group and 3 — Black mouth Proboxy groups are exposed, and
  • X is an oxygen atom and a sulfur atom.
  • n represents an integer of 0 to 5
  • Y when m is an integer of 2 to 5 and Y is the same or different, Y may be the same or different.
  • n 1 or 2.
  • Q ' represents cyano, carboxy, methoxycarbonyl, ethoxycarbonyl, n-propoxy Nil group, io — Propoxy carbonyl group n Butoxy carbonyl group
  • the substituent z is a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a methyl group, an ethyl group, n-propyl group, iso-propyl group, n-butyl , Is 0 —butyl group, sec —butyl group, tert —butyl group, methoxy group, ethoxy group, n —propoxy group, iso —pro Pox group, n — butoxy group, iso — butoxy group, sec — plastic, ter butoxy, difluoromethyl, trif Chloromethyl group, chloromethyl group, bromomethyl group, phenyl chloromethyl group, 2 — chloromethyl group, dichloromethyl group Roxy meter base, trifluorometer base, 2, 2, 2 — Trifluoroethoxy group, 2 — Cross mouth outlet group, 3 — Gro mouth Si group, methylthio group, e
  • R 4 represents a hydrogen atom, a methyl group, an ethyl group, n—propyl group, is 0—propyl group, II—butyl group, iso—butyl group , Sec —
  • the compound of the present invention having a butyl group and a terbutyl group is used as a herbicide for upland fields, paddy fields, and non-cultivated lands. It can be used in any of the processing methods.
  • the target weeds as the herbicides of the compound of the present invention include wild solgum, oaksakibi, johnsongrass, inubie, mexisino Grass weeds such as oak grass, ohisiba, enocologusa, suzumenotetsubo, etc .; ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ Mouth, Kikashidasa, Tainubie, etc. are exposed.
  • the compounds of the present invention are important crops such as wheat, corn, barley, Contains compounds that can be used safely in soybeans, rice, cotton, beats, solgum, etc.
  • the compound of the present invention is also useful as a defoliant (defo1iant).
  • the compound of the present invention can be synthesized, for example, by the methods shown in the following schemes 1 to 3.
  • (R 1 R 2 , R 3 , X, Y, Q, Q ′, m and n in the schemes 1 to 3 have the same meanings as described above, and Ha 1 is a halogen. Represents an atom.
  • Scheme 1 synthesizes intermediate c by reacting benzylamine derivative a with ⁇ -nitrogenoketon derivative b, and synthesizes intermediate c.
  • the reactive compound d of the acetic acid derivative is reacted to form an N-benzylamide derivative e, and finally, the N-benzylamide derivative e is closed.
  • Aliphatic hydrocarbons such as petroleum ether, aromatic hydrocarbons such as benzene, toluene, xylene, black benzene, black mouth Halogenated hydrocarbons such as salified methylene, ethers such as ethyl ether, dioxan, tetrahydrofuran, etc .; Ketones such as seton, methyl etholetone, etc .; nitriles such as acetonitrile, isopyronitrile, pyridin; N, N — tertiary amines such as ethyl aniline, N, N — dimethyl acetate amide, NN — dimethyl honole amide, N — Acid amides such as methylenpyrrolidone, sulfur-containing compounds such as dimethyl sulfoxide and sulfolane, and mixtures thereof
  • the aliphatic hydrocarbons, aromatic hydrocarbons, ethers, ketones, nitriles such
  • a trinitroquinamine NN is a nitrogen-containing organic base such as dimethylanilin.
  • the reaction temperature is usually from 0 to 200 ° C, preferably from room temperature to the reflux temperature of the reaction mixture.
  • Reaction time is usually from 10 minutes to 96 hours, preferably from 30 minutes to 24 hours
  • Examples of the reactive compound d of the acetic acid derivative include an acid anhydride, an acid chloride, an acid bromide, an active ester, and the like.
  • Hexane, heptane, rig mouth In aliphatic hydrocarbons such as petroleum ether, benzene, toluene, xylene, black mouth as solvents
  • Aromatic hydrocarbons such as benzene, halogenated hydrocarbons such as chloroporous chloromethane, methylene chloride, etc., ethyl ether, dioxane, Ethers such as trahydrofuran, etc., ketones such as aceton, methionole etholetone, etc., acetonitrile and isopuchi.
  • N-trinoles such as _-lonitrinole, pyridine, N, N — tertiary amines such as dimethylanilin, N, N — dimethyl Acid amides such as acetate amide, NN—dimethylaminoformamide, N—methylpyrrolidone, dimethylsulfoxide, Sulfur-containing compounds such as phorolane, water and mixtures thereof are preferred, and the above-mentioned aliphatic hydrocarbons, aromatic hydrocarbons, halogenated hydrocarbons are preferred. , Ethers, ketones, nitriles, acid amides, sulfur-containing compounds and mixtures thereof.
  • a base for the reaction it may be better to use a base for the reaction. In that case, 0.5 to 10 equivalents, preferably 0.8 to 3.0 equivalents, of the base is used.
  • the reaction is usually carried out at a temperature of from 130 to 150 ° C, preferably from -10 ° C to the reflux temperature of the reaction mixture.
  • the reaction time usually ranges from 10 minutes to 48 hours, preferably from 30 minutes to 24 hours.
  • e is usually closed in the presence of a base.
  • the reaction usually requires a solvent, and the solvent may be aliphatic hydrocarbons such as hexane, heptane ligne, petroleum ether, benzene and toluene.
  • Aromatic hydrocarbons such as benzene, xylene, and chlorobenzene, halogenated hydrocarbons such as chlorobenzene and methylene chloride, and methyl ether Ethers such as tel, dioxan, tetrahydrofuran, etc., ketones such as acetone, methylethylenoketone, etc., and acetate Nitrites such as nitrinoles and isoptinitronitrile; tertiary amines such as pyridin; N, N-diethylanilinine; N , N — Dimethyl acetate amide, N, N — Dimethyl honolem amide, N — Acid amides such as methylpyrrolidone, dimethylSulfur-containing compounds
  • pyridin triethylenamine, N, N—dimethylaminolinine, N, N—dimethylalanine, 41 (N, N — Nitrogen-containing organic bases, such as dimethylaminoamino) pyridin and 1,4-diazabicyclo [2.2.2] octane, hydrogenated sodium Inorganic bases such as hydrogen hydride, sodium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, etc. , Sodium ethoxide, metal alkoxides, such as potassium tert-butoxide, sodium methyl ester, sodium methyl ester Metal alkyl alcohols, such as trimethyl alcohol, etc., are preferably used.
  • sodium hydroxide, hydroxide are used.
  • the reaction temperature is usually from 0 to 200 ° C., preferably from room temperature to the reflux temperature of the reaction mixture.
  • the reaction time usually takes 2 minutes to 24 hours, preferably 5 minutes and 12 hours.
  • the reaction proceeds in the second stage reaction to the third stage ring closure reaction.
  • L 0 equivalent preferably 0.8 to 3 equivalent is used for a.
  • the reaction proceeds without solvent, but it is possible to use a solvent.
  • Aliphatic hydrocarbons such as hexane, heptane, rig mouth, petroleum ether, benzene, toluene, xylene, and chlorene as solvents.
  • Aromatic hydrocarbons such as benzene and benzene, halogenated hydrocarbons such as chloromethane and methylene chloride, dimethyl ether, and dioxa Ketones such as acetates, methyl ketones, etc., acetates, etc.
  • Nitrites such as petitlonitrile, N, N — dimethyl acetate amide, N, N — dimethylformamide, N — methyl Acid amides such as pyrrolidone, sulfur-containing compounds such as dimethyl sulfolide and sulfolane, water, and mixtures thereof.Et al Re that.
  • the reaction temperature is usually from 130 to 150 ° C, and preferably from 110 ° C to the reflux temperature of the reaction mixture.
  • the reaction time is usually between 10 minutes and 96 hours, preferably 30 minutes.
  • G can be isolated by distilling off low-boiling compounds after the reaction is completed.
  • the amidation reaction can be carried out under the same reaction conditions as in the second stage of Scheme 1.
  • the ring closure reaction can be performed under the same reaction conditions as in the third step of Scheme 1.
  • the reaction may proceed to the third stage ring closure reaction.
  • Scheme 3 represents a method for producing the compound (11-B) of the present invention by reducing the cyclic (thio) amide compound i.
  • the reducing agent is usually present in an amount of 0.5 to L; equivalent to i, preferably _ _
  • the reaction usually uses a solvent
  • the solvent may be aliphatic hydrocarbons such as hexane, heptane, rig mouth, petroleum ether, benzene, toluene, etc.
  • Aromatic hydrocarbons such as benzene, xylene, and chlorobenzene, halogenated hydrocarbons such as chlorobenzene and methylene chloride, and dimethylene Ethers such as ter, dioxan, tetrahydrofuran, etc., ketones such as aceton, methino ole ethole ketone, etc.
  • Nitrils such as tonitrile and isopyronitrile, liquid ammonia, pyridin, N, N—N-N-N Mines, N, N—Dimethyl acetate amide, N, N—Dimethyl honolem amide, N—Methyl pyrrolidone and other acids Sulfur-containing compounds such as mids, dimethyl alcohol and sulfolane, and alcohols such as methanol, ethanol and propanol , And the power of mixtures thereof, and the above-mentioned aromatic hydrocarbons, ethers, amines, alcohols, and the like And a mixture of these.
  • the reaction is usually carried out at a temperature of from 150 to 200 ° C., preferably from 150 ° C. to the reflux temperature of the reaction mixture.
  • the reaction time usually takes 5 minutes to 96 hours, preferably 15 minutes to 48 hours.
  • recrystallize Separation and purification can be performed by any purification method such as mucous chromatography.
  • compounds having an asymmetric carbon include optically active (+) and (1) isomers.
  • Reference Example 1 1 (3—chloro ⁇ , ⁇ —dimethylbenzylamino) 1-2—prono, synthesized in Example 1.
  • Example 1 (chloro ⁇ , ⁇ —dimethylbenzylamino) 1-2—prono, synthesized in Example 1.
  • Ql, Q2, Q3, Q4, Q5, Q19, Q21, Q1, Q42, Q43, Q53, Q54 and Q66 Does the following,
  • ⁇ e is a methyl group
  • Et is an ethyl group
  • Pr is a propynolyl group
  • Bu is a methyl group
  • Ph is a phenyl group
  • t evening Represents
  • Examples of the compounds of the present invention synthesized according to the above-mentioned scheme or Example 6 include the above compounds A-1 to A-68 and B-1 to B-18. As shown in Tables 3-1 and 3-2, the present invention is not limited by these.
  • Me is a methyl group
  • Et is an ethyl group
  • Pr is a propynol group
  • Bu is a butyl group
  • Ph represents a phenyl group
  • i represents an iso
  • t represents evening
  • a suitable carrier for example, Cray, tanolek, bentonite, silica, etc.
  • Solid carriers such as algae soil white carbon, or water, alcohols (isoprono, phenol, butanol, pentanoreal) Calls, phenolic furyl alcohol, etc.), aromatic carbohydrates (toluene, xylene, etc.), ethers (anisoles) ), Ketones (cyclohexanone, isophorone), esters (butyric acid ester, etc.), acid ⁇ ⁇
  • liquid carriers such as benzenes (eg, methylpyrrolidone) or halogenated hydrocarbons (eg, chlorbenzen).
  • surfactants eg, emulsifiers, dispersants, penetrants, spreading agents, thickeners, antifreezing agents, anti-caking agents, stabilizers, disintegrators, etc. It can be put into practical use in any form such as wettable powder, dry flowable, flowable, powder, granule, gel and the like.
  • the compound of the present invention may be mixed with other kinds of herbicides, various insecticides, fungicides, plant growth regulators, synergists and the like at the time of preparation or spraying.
  • the combined use with other herbicides reduces the cost by reducing the amount of applied herbicide, and reduces the herbicidal spectrum due to the synergistic effect of the mixed herbicide. It can be expected to expand and have higher herbicidal effects. At this time, it is possible to combine with several known herbicides at the same time.
  • the types of herbicides to be used in combination with the compound of the present invention include, for example, farm chemicals and hoods (Farm Chemicals H andook). There are compounds listed in the 1991 edition.
  • the amount of the compound of the present invention applied as a herbicide may vary depending on the application scene, time of application, application method, cultivated crops, etc., but generally, the effective component amount is hectare ( ha) 0.0000 per ⁇ : L 0 kg Approximately, preferably about 0.001 to 5 kg.
  • anti-caking agents include anti-caking agents and the like.
  • Surfactant 0.1 to 12 parts Other 0.30 parts, for example, deicing agents, thickeners, etc.
  • Compound of the present invention 20 to 90 parts Solid carrier 9 to 60 parts Surfactant 1 to 20 parts Other 0 to 40 parts Others include, for example, disintegrants and the like. .
  • the above is uniformly mixed and ground to form a wettable powder.
  • Non-ionic surfactant Kao Corporation
  • Ethylene glycol (antifreeze) 8 parts Mix 28.5 parts or more of water evenly to obtain a flowable agent
  • the above is uniformly mixed and pulverized to make a dry flowable.
  • the above is uniformly mixed and ground to form a wettable powder.
  • Agri-Resolution S — 7 1 1 8 copies (Non-ionic surfactant: Kao Corporation)
  • the above is uniformly mixed and pulverized to obtain a dry flowable agent.
  • the above-mentioned wettable powders, emulsions, flowables and granular hydration agents are diluted 50 to 100 times with water to obtain an active ingredient of 1
  • an active ingredient of 1 One one
  • the extent of suppression was determined by visual observation.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Hydrogenated Pyridines (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyrrole Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

Composé amide cyclique représenté par la formule générale (1-A) ou (1-B), et herbicide le contenant. Dans ces formules, R?1, R2 et R3¿ représentent chacun hydrogène ou alkyle; X représente oxygène ou soufre; Y représente halogène, alkyle, etc.; m représente un entier compris entre 0 et 5; n représente 1 ou 2; Q représente un hétérocycle, naphtyle, un hétérocycle condensé, etc.; et Q' représente phényle, hétérocycle, naphtyle, hétérocycle condensé, etc.
PCT/JP1993/001406 1992-10-05 1993-10-01 Compose amide cyclique et herbicide WO1994007857A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU48346/93A AU4834693A (en) 1992-10-05 1993-10-01 Cyclic amide compound and herbicide

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP4/266263 1992-10-05
JP26626392 1992-10-05
JP5218667A JPH06172306A (ja) 1992-10-05 1993-09-02 環状アミド化合物および除草剤
JP5/218667 1993-09-02

Publications (1)

Publication Number Publication Date
WO1994007857A1 true WO1994007857A1 (fr) 1994-04-14

Family

ID=26522687

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP1993/001406 WO1994007857A1 (fr) 1992-10-05 1993-10-01 Compose amide cyclique et herbicide

Country Status (4)

Country Link
JP (1) JPH06172306A (fr)
CN (1) CN1085218A (fr)
AU (1) AU4834693A (fr)
WO (1) WO1994007857A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999052893A1 (fr) * 1998-04-08 1999-10-21 Novartis Ag Nouveaux herbicides au n-pyridonyle
WO2001017964A1 (fr) * 1999-09-03 2001-03-15 Syngenta Participations Ag Tetrahydropyridines
CZ298120B6 (cs) * 1996-09-25 2007-06-27 Gpi Nil Holdings, Inc. Heterocyklické thioestery nebo ketony

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3525499B2 (ja) * 1994-07-25 2004-05-10 日産化学工業株式会社 固形農薬組成物
ES2886441T3 (es) * 2014-04-29 2021-12-20 Fmc Corp Herbicidas de piridazinona

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH02225459A (ja) * 1989-01-07 1990-09-07 Bayer Ag ３―アリール―ピロリジン―２，４―ジオン誘導体
JPH0399059A (ja) * 1989-08-29 1991-04-24 Bayer Ag ４―アルコキシ‐および４‐（置換された）アミノ‐アリールピロリノン誘導体類
JPH03204855A (ja) * 1988-12-09 1991-09-06 Kumiai Chem Ind Co Ltd 環状アミド誘導体および除草剤

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH03204855A (ja) * 1988-12-09 1991-09-06 Kumiai Chem Ind Co Ltd 環状アミド誘導体および除草剤
JPH02225459A (ja) * 1989-01-07 1990-09-07 Bayer Ag ３―アリール―ピロリジン―２，４―ジオン誘導体
JPH0399059A (ja) * 1989-08-29 1991-04-24 Bayer Ag ４―アルコキシ‐および４‐（置換された）アミノ‐アリールピロリノン誘導体類

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CZ298120B6 (cs) * 1996-09-25 2007-06-27 Gpi Nil Holdings, Inc. Heterocyklické thioestery nebo ketony
WO1999052893A1 (fr) * 1998-04-08 1999-10-21 Novartis Ag Nouveaux herbicides au n-pyridonyle
WO2001017964A1 (fr) * 1999-09-03 2001-03-15 Syngenta Participations Ag Tetrahydropyridines
US6638940B1 (en) 1999-09-03 2003-10-28 Syngenta Crop Protection, Inc. Tetrahydropyridines as pesticides

Also Published As

Publication number Publication date
JPH06172306A (ja) 1994-06-21
AU4834693A (en) 1994-04-26
CN1085218A (zh) 1994-04-13

Similar Documents

Publication Publication Date Title
EP4053125B1 (fr) Procédé pour la production d'un herbicide pyroxasulfone
AU2002327096B2 (en) 3-phenoxy-4-pyridazinol derivative and herbicide composition containing the same
CN1040940C (zh) 含4－苯甲酰异噁唑衍生物的组合物及其用途
CN1036305C (zh) 除草组合物及其应用
WO1993021162A1 (fr) Derive de 2-arylaminopyrimidinone, et herbicide et regulateur de la croissance vegetale contenant ce compose
EP0532022A1 (fr) Composés acryliques, procédé pour leur préparation et fongicides les contenant
EP0888359A1 (fr) Derives de pyrimidine-4-one utilises comme pesticide
AU2326801A (en) Herbicidal imidazolidinetrione and thioxo-imidazolidinediones
CN107249329A (zh) 新的异噻唑酰胺、其制备方法及其作为除草剂和/或植物生长调节剂的用途
WO1994007857A1 (fr) Compose amide cyclique et herbicide
JPH04128275A (ja) Ｎ―ベンジルアミド類およびこれを有効成分とする殺虫、殺ダニ剤
EP0354766A2 (fr) Dérivés de 2,4-diphénylpyrimidine 5-substitués, leur production et utilisation comme herbicide
WO2003000659A1 (fr) Composes heterocyclo-iminophenyle et fungicides et insecticides destines a l'agriculture et l'horticulture
WO1995012582A1 (fr) Nouveau derive de pyrimidine disubstitue en positions 4 et 5 et herbicide
KR940005013B1 (ko) 3,4-트란스-4-에틸-1-(치환된 페닐)-3-(치환된 페닐)피롤리딘-2-온, 그 제조방법 및 제초적 활성 성분으로서 그것을 함유하는 제초 조성물
EP0387869B1 (fr) Dérivés de la 4-éthyl-3-(phényl-substitué)-1-(3-trifluorméthyl-phényl)-2-pyrrolidinone, procédé de préparation et applications, compositions herbicides contenant ces composés
WO1998012184A1 (fr) Composes de pyrimidine, procede de preparation correspondant et agents de lutte antiparasitaire
JP3074658B2 (ja) アラルキルアミノピリミジン誘導体、その製法及び有害生物防除剤
JPH04210971A (ja) 置換β−ピリミジニルオキシ（チオ）−およびβ−トリアジニルオキシ（チオ）−シクロアルキルカルボン酸誘導体、その製造方法、これを含有する除草、殺虫および植物生長調整効果のある薬剤およびその薬剤の製造方法
JP2728937B2 (ja) １―（３―置換ベンジル）―３―ハロゲノ―４―（１―ハロゲノアルキル）―２―ピロリジノン誘導体およびこれらを有効成分とする除草剤
JPH08245594A (ja) ２−オキシアニリン誘導体および除草剤
JP2003231672A (ja) オキシム型化合物又はその塩類及び農園芸用殺菌剤
JP4229310B2 (ja) 置換ベンジルピペリジン誘導体およびこれを含有する殺虫剤
JP2837340B2 (ja) ３−アザビシクロ［３．１．０］ヘキサン−２−オン誘導体、およびこれらを有効成分とする除草剤
BR112022008144B1 (pt) Processo para a produção de um composto derivado de sulfona

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AU BG BR CA CZ FI HU KR NO NZ PL RO RU SK UA US VN

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH DE DK ES 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
DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
122 Ep: pct application non-entry in european phase
NENP Non-entry into the national phase

Ref country code: CA

点击 这是indexloc提供的php浏览器服务，不要输入任何密码和下载