WO2000050397A1 - Derives substitues de la piperidinedione et herbicide - Google Patents

Derives substitues de la piperidinedione et herbicide Download PDF

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Publication number
WO2000050397A1
WO2000050397A1 PCT/JP2000/001062 JP0001062W WO0050397A1 WO 2000050397 A1 WO2000050397 A1 WO 2000050397A1 JP 0001062 W JP0001062 W JP 0001062W WO 0050397 A1 WO0050397 A1 WO 0050397A1
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Prior art keywords
group
groups
alkyl
alkoxy
so2ch3
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PCT/JP2000/001062
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English (en)
Japanese (ja)
Inventor
Yasuo Yamada
Hiroyuki Adachi
Masahiko Kato
Akihiro Takahashi
Masami Koguchi
Shigeo Yamada
Katsunori Tanaka
Satoshi Kajita
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Nippon Soda Co., Ltd.
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Priority to AU26911/00A priority Critical patent/AU2691100A/en
Priority to JP2000600980A priority patent/JP4597379B2/ja
Publication of WO2000050397A1 publication Critical patent/WO2000050397A1/fr

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    • 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
    • A01N43/48—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
    • 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
    • A01N43/80—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 1,2
    • 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
    • C07D211/80—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 two double bonds between ring members or between ring members and non-ring members
    • C07D211/84—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 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 directly attached to ring carbon atoms
    • C07D211/86—Oxygen atoms

Definitions

  • the present invention relates to a substituted piperidine derivative in which a benzoyl group is substituted at the 3-position of piperidine, and a herbicide.
  • the present invention provides: (a) a compound represented by the general formula (1):
  • R 1 and R 2 each independently represent a nitrogen atom, a cyano group, a halogen atom
  • C alkyl group, alkoxy group, C i - represents a 6 haloalkyl group, C i-s Al Kiruchio group, an alkyl sulfide alkylsulfonyl group or a C alkylsulfonyl group.
  • -R 3 is a nitro group, a cyano group, a halogen atom, an alkyl group, a C! -E alkoxy group, a C, -haloalkyl group, a Ci-alkylthio group, a C! -Alkylsulfinyl group or a C alkyl Represents a sulfonyl group.
  • n 0, 1, and 2.
  • R 4 and R 5 are each independently a hydrogen atom, a halogen atom, an alkyl group, a C i -haloalkyl group, a C i -alkoxy C alkyl group, an alkylcarbonyloxy C alkyl group, a hydroxy C i- 6 alkyl Represents a group, and R 4 R 5 may be taken together to form an alkylene chain having 25 carbon atoms
  • R 6 represents a hydrogen atom, a d- 6 alkyl group, a hydroxy 6 alkyl group, or a C! -S haloalkyl group. However, when R 6 is a hydrogen atom, n is not 0.
  • R 7 is an alkyl group, human Dorokishi Jii 6 alkyl group, a Haroaruki group, also, R 6 R 7 may form a form a connexion alkylene chain having a carbon number of 2 5 a together, made et al R 7 may combine with R 5 to form a bond or an alkylene chain having 1 to 4 carbon atoms.
  • R 8 represents a hydrogen atom, an alkyl group, C 2 6 alkenyl, C 2 6 Arukini Le groups, C haloalkyl group, C 2 haloalkenyl group, C 2 haloalkynyl groups, C t - e alkoxy group, C 2 6 alkenyl It represents a 6 Arukiniruokishi group, C i- ⁇ Roarukokishi group, c 2 6 haloalkenyl O alkoxy group, c 2 ⁇ Roaru Kiniruokishi group - Okishi group, C 2.
  • the optionally substituted heterocyclic group may be any of the following groups
  • R 11 and R 12 each independently represent a hydrogen atom, a halogen atom, a -6 alkyl group or an alkoxy group.
  • R 1 and R 2 each independently represent a nitro group; a cyano group; a halogen atom such as fluorine, chlorine, or bromine; a methyl, ethyl, propyl, isopropyl, butyl, t - C and butyl - 6 alkyl group;!
  • R 3 is a nitro group; a cyano group; a halogen atom such as fluorine, chlorine, and bromine; a 6- alkyl group such as methyl, ethyl, propyl, isopropyl, butyl, and t-butyl; Ci-6 alkoxy groups such as toxic, ethoxy, propoxy, isopropoxy, butoxy, and t-butoxy; trifluoromethyl, trichloromethyl, fluoromethyl, chloromethyl, difluoromethyl, dicyclomethyl Ci-ii haloalkyl groups such as lorometyl, trifluorethyl, pendufluorethyl, etc .; C!
  • alkylthio groups such as methylthio, ethylthio, propylthio, isopropylthio; methyl sulfinyl, ethyl sulfinyl, ! 6 alkyl sulfide alkylsulfonyl groups - professional Pirusurufi nil, C, such as Lee Sopuro Pirusuru Fi nil Other eyes Chirusuruhoniru, Echiru sulfonyl, professional Pirusuruhoniru, C, such as Lee Sopuro Pirusuruhoniru! — (; Represents an alkylsulfonyl group.
  • R 4 and R 5 are each independently a hydrogen atom; a halogen atom such as fluorine, chlorine, or bromine; methyl, ethyl, propyl, isopropyl, butyl, isoptyl, t
  • —Ci-S alkyl group such as butyl; C such as trifluorethyl, trichloromethyl, fluoromethyl, chloromethyl, dichloromethyl, difluoromethyl, trifluorethyl, pentafluoroethyl, etc. i- 6 alkyl group; methoxymethyl
  • Ci- 6 alkylcarboxyloxy CS alkyl group such as acetyloxymethyl, ethylcarbonyloxymethyl, acetyloxethyl, etc .
  • hydroxy c such as hydroxymethyl, hydroxypropyl, and hydroxypropyl!
  • R 4 and R 5 are joined together to form ethylene, trimethylene, An alkylene chain having 2 to 5 carbon atoms such as tetramethylene and pentamethylene may be formed.
  • R 6 is a hydrogen atom; methylation, Echiru, propyl, i Sopuro pills, heptyl, Lee Seo heptyl, C i alkyl group such as t _ butyl; human Dorokishime chill, heat, such as heat Dorokishe chill Dorokishi C i - 6 Alkyl group; C ⁇ 6 haloalkyl group such as trifluorethyl, trichloromethyl, fluoromethyl, chloromethyl, trimethyl, dichloromethyl, difluoromethyl, trifluorethyl, pendufluorethyl, etc. Represents
  • R 7 is methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t
  • Alkyl groups such as butyl; hydroxymethyl alkyl groups such as hydroxymethyl and hydroxyshethyl; Represents C i haloalkyl groups such as tyl, trifluoroethyl, and pentafluoroethyl
  • R 6 and R 7 may be taken together to form an alkylene chain having 2 to 5 carbon atoms, such as ethylene, trimethylene, tetramethylene, and pentamethylene. Further, R 7 and R 5 may be taken together to form a bond or an alkylene chain having 1 to 4 carbon atoms such as methylene, ethylene, trimethylene, and tetramethylene.
  • R 8 is a hydrogen atom, methylation, Echiru, propyl, i Sopuro pills, heptyl, Lee Su Wu chill, t -! C and butyl - alkyl group, vinyl, ⁇ Li Le, 2 - C 2, such as butenyl - 6 alkenyl group, Echiniru, 2 - C 2 such pro pinyl - 6 alkynyl group, Application Benefits Furuorome chill, Application Benefits click Rorome chill, Furuorome chill, click Rorome chill, diphenyl Ruorome chill, Jikurorome chill, Application Benefits Furuoroechiru, Pentafuruo Roechiru of any C -!
  • C 2 — 6 haloalkenyloxy groups such as, 2 — difluorovinyloxy, 3 — chloroallyloxy, 3, 3 — dichloroallyloxy, 2 — chloroallyloxy, 2-chloroethynyloxy, 3 _ black port one 2 - propynyl O carboxymethyl, 3 - represents a 6 haloalkynyl O dimethylvinylsiloxy groups - fluoroalkyl one 2 - C 2 such as propynyl O alkoxy.
  • Z is a formyl group; a morpholino group; C! Such as methoxy, ethoxy, propoxy, and isopropoxy.
  • C, - represents a 6 haloalkyl group, main butoxycarbonyl, et butoxy C i-S alkoxycarbonyl good full
  • Z represents a saturated or unsaturated 5- to 6-membered heterocyclic group containing 1 to 4 N, 0 or S atoms and optionally having substituents R 11 and R 12 . This heterocyclic group is bonded to the benzene ring at a carbon atom.
  • Preferred heterocyclic groups include, for example, 2-furyl, 3_furyl, oxazole-2-yl, oxazolu-l 4-yl, oxazolu-l-5-yl, isoxox-l-ru 3 Yl, oxoxazoluru 4 yl, isoxoxazolu — 5 — yl, 1, 2, 4 — oxadiazol — 3 — yl, 1, 2, 4 — oxaziazoluru 5 — yl, 1, 3, 4-Oxaziazol 2-yl, thiazo 1-2-yl, thiazo 1-4-yl, thiazo 1-5 1-yl, isotiazole—3—yl, isotiazole—41—yl, isotizazol—5—yl, s 2,4—thiadiazol—3—yl, s 2, 4—thiaasia Zolulu 5 — yl, 1, 3, 4
  • the heterocyclic group may be substituted at any position with a substituent RH, such as a halogen atom such as fluorine, chlorine and bromine, a Ct- 6 alkyl group such as methyl and ethyl, and an alkoxy group such as methoxy and ethoxy. it may have a R 12.
  • a substituent RH such as a halogen atom such as fluorine, chlorine and bromine, a Ct- 6 alkyl group such as methyl and ethyl, and an alkoxy group such as methoxy and ethoxy. it may have a R 12.
  • heterocyclic group examples include the following groups.
  • R 11 and R 12 each independently represent a hydrogen atom, a halogen atom, an ealkyl group, or a Ct - 6 alkoxy group.
  • R 9 represents a hydrogen atom or an alkyl group such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl and t-butyl; a hydroxy group; methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl; C- 6 alkyl group such as monobutyl; trifluoromethyl, trichloromethyl, fluoromethyl, chloromethyl, Jifuruoromechiru, dichloromethyl, Application Benefits Furuoroechiru, C alkyl group such as penta full O Roe Chi le; vinyl, 1 - propenyl, C 2 such Ariru, crotyl, blanking evening Jeniru - 6 alkenyl group; 2 - chloro vinyl, 2 2 - Jifuruoro vinyl,
  • R 1 , R 2 , R 3 , R 4 , R 5 , R e , R 7 , R 8 , n and Z have the same meanings as described above, and Q is a halogen atom, an alkylcarbonyloxy group Represents an alkoxycarbonyloxy group or a benzoyloxy group.
  • the compounds (3a) and (3b) are prepared by mixing 1 mol of the compound (2) with ArC0Q (where Ar and Q have the same meanings as described above) or one of them. It is obtained by using in excess and reacting in the presence of 1 mole or an excess of base.
  • Bases used in the reaction include alkali metal hydroxides such as K ⁇ H, Na ⁇ H, alkali metal carbonates such as sodium carbonate and potassium carbonate, and calcium hydroxide.
  • Alkaline earth metal hydroxides such as magnesium hydroxide, alkaline earth metal carbonates such as calcium carbonate, triethylamine, triisopropylamine, and tri (C alkyl) amines such as diisopropylpropylamine.
  • Examples include organic bases such as gin, sodium phosphate, and the like.
  • solvent examples include water, methylene chloride, chloroform, toluene, and ethyl acetate.
  • the reaction mixture is stirred at 0 ° C to 50 ° C until the reaction is completed.
  • the reaction can also be carried out in a two-phase system using a phase transfer catalyst such as a quaternary ammonium salt.
  • the compounds (3a) and (3b) are obtained by converting the compound (2) and the compound ArC00H (Ar represents the same meaning as described above) with a dicyclohexylcarbodiimide (DCC )) In the presence of a dehydrating condensing agent.
  • DCC dicyclohexylcarbodiimide
  • a dehydrating condensing agent As the solvent used in the reaction with DCC, etc., methylene chloride, chloroform, toluene, ethyl acetate, DMF, THF, DME, acetonitrile and the like are used.
  • the reaction mixture is stirred at ⁇ 10 ° C. to 50 ° C. until the reaction is completed.
  • the reaction mixture is worked
  • Compounds (3a) and (3b) are used as a mixture in the next rearrangement reaction.
  • the rearrangement reaction is performed in the presence of a cyanide and a mild base. That is, one mole of the compounds (3a) and (3b) is replaced by 1 to 4 moles of base, preferably 1 to 2 moles of base and 0.01 to 1.0 moles, preferably Is to obtain the compound (1a) by reacting with 0.05 to 0.2 mol of a cyanide compound.
  • the base used here any of the above bases can be used.
  • the cyanide compound potassium cyanide, sodium cyanide, acetate cyanide hydride, hydrogen cyanide, a polymer holding potassium cyanide, and the like are used.
  • the reaction is completed in a shorter time by adding a small amount of a phase transfer catalyst such as crown ether.
  • a phase transfer catalyst such as crown ether.
  • the reaction is carried out at a temperature lower than 80 ° C, preferably at 20 to 40 ° C.
  • the solvents used are 1,2-dichloroethane, toluene, acetonitrile, methylene chloride, ethyl acetate, DMF, methyl isoptyl ketone, THF, DME, and the like.
  • Compound (la) is prepared by reacting compound (2) with ArCoCN (Ar represents the same meaning as described above) in the presence of a base and, if necessary, a Lewis acid according to the following method. It can also be obtained.
  • Bases used are alkali metal hydroxides such as KOH and NaOH, hydroxides of alkaline earth metals such as magnesium hydroxide and calcium hydroxide, and triethyl.
  • ⁇ Mi emissions Application Benefits such as diisopropyl Sopuro Piruechirua Mi emissions (C -! 6 alkyl) ⁇ Mi emission, organic bases such as pin lysine, carbonate Na Application Benefits um, and the like phosphate Na Application Benefits um.
  • Suitable Lewis acids include zinc chloride, aluminum trichloride and the like, preferably zinc chloride.
  • the compound (1c) is a compound (lb) (wherein R 13 represents a lower branched alkoxy, araalkyloxy, or acetoxy), and chlorine, odor or the like.
  • R 13 represents a lower branched alkoxy, araalkyloxy, or acetoxy
  • chlorine, odor or the like Manufactured by reaction with hydrohalic acids such as hydrofluoric acid, trifluoroacetic acid, boron tribromide, etc., by hydrogenolysis or alkaline hydrolysis, and, if necessary, by subsequent hydrolysis be able to.
  • the compound (1c) is converted into a compound (Id) (L is a leaving group by subjecting the compound to a halogenation, alkylsulfonation or arylsulfonation by an ordinary method. Logen, alkylsulfonate, arylsulfonate, etc.).
  • the compound (1e) is obtained by converting the compound (Id) into a In the presence, from ⁇ 20 to the boiling point of the solvent used, preferably from room temperature to 100,
  • It can be produced by reacting from 30 minutes to several 10 hours.
  • the base used is an alkali metal hydroxide such as KOH or NaOH, a hydroxide of an alkaline earth metal such as magnesium hydroxide or calcium hydroxide, triethylamine, diisopropylamine.
  • the solvents used include water, alcohol, methylene chloride, benzene, toluene, ethyl acetate, DMF, THF, DME, and acetonitrile.
  • a r C 0 Q (A r and Q have the same meaning as described above) and A r C CH (A r has the same meaning as described above) are to be produced according to a known method. Can be.
  • the cyclic dione compound represented by the general formula (2) can be produced according to the following route.
  • R 5 , R 6 , R 7 and R 8 represent the same meaning as described above, and R 4 represents a group shown in the figure.
  • R 14 and R 15 represent a lower alkyl group;
  • Y represents a halogen atom Represent.
  • the compound (6) is equimolar or in excess of the compound (5) obtained by a known method from the compound (4) and R 8 NH 2 (where R 8 has the same meaning as described above).
  • R 15 is the same as the table to.
  • the base used is an alkali metal hydroxide such as KOH or NaOH, an alkali metal carbonate such as sodium carbonate or potassium carbonate, or an alkali metal such as calcium hydroxide or magnesium hydroxide.
  • Bases sodium phosphate and the like.
  • Solvents used include methylene chloride, chloroform, toluene, ethyl acetate, DMF, THF, DME, and acetonitrile.
  • the reaction is carried out between 110 ° C. and the boiling point of the solvent used.
  • the obtained compound (6) was converted to an organic compound in the presence of a base of an equimolar to triple alkali metal alcoholate such as sodium ethylate or a metal hydride such as sodium hydride.
  • the compound (7) is obtained by reacting in a solvent at a temperature between 0 ° C and the boiling point of the solvent, followed by neutralization with an inorganic acid such as hydrochloric acid.
  • examples of the solvent used for the reaction include alcohols such as ethanol and methanol, ethers such as THF and DME, hydrocarbons such as toluene and xylene, and DMF. .
  • Solvents used include methylene chloride, chloroform, toluene, ethyl acetate, DMF, THF, dioxane, DME, and acetonitrile.
  • the compound (2b) can be prepared by reacting the compound (2a) in a solvent in the presence of a base in the presence of a base, and the electrophilic reagent R 4 Y (where R 4 represents a group shown in the figure; Y represents a halogen atom.) And —78 ° C. to the boiling point of the solvent used.
  • Solvents used are ether, THF, benzene, toluene and hexane.
  • the base to be used include alkyl lithium, lithium diisopropylamide and the like.
  • Acrylic acid derivatives, benzoic acid ester aldehydes and intermediates thereof, benzoic acid ester carboxylic acids and intermediates thereof, intermediates having a heterocyclic ring, etc. of compound (4) used as raw materials Can be produced by a known method described in, for example, W098 / 29412, W098 / 56676, and JP-A-10-338675.
  • a salt thereof particularly an agriculturally and horticulturally acceptable salt, enamine or an analog thereof, or an acylate may be prepared from the compound.
  • Sulfonates and carbamates can induce ethers, polyesters, sulfoxides or sulfones.
  • Suitable agriculturally and horticulturally acceptable salts include salts of sodium, calcium, calcium and ammonium.
  • ammonium salts include those of the formula: N + R a R b R c R d (where R a, R b, R c and R d are each independently hydrogen and optionally a hydroxy group , Which is an alkyl group).
  • R a, R b, 1 (: 1 and 1 (1 is an optionally substituted alkyl group, these may contain 1 to 4 carbon atoms. Desirable.
  • Suitable enamines or analogs thereof are those in which each of the ⁇ H moieties is of the formula: — NR e R f (where the shaku 6 ⁇ ! Is independently hydrogen or, for example, having 1 to 6 carbon atoms. , Halogen, S (0) gRh (where Rh is, for example, 1 to 6 carbon atoms), optionally substituted alkyl or aryl groups such as phenyl groups. Is an optionally substituted alkyl or aryl group, for example a phenyl group, and g represents 0 to 2.).
  • Suitable acylate, ether or olebamate derivatives are those in which the OH moiety has the formula: — ⁇ C ORi, one ORj or one OCONR k R l, where R i and R j Has the same meaning as Rh described above, and Rk and R1 have the same meanings as Re described above.)
  • These derivatives can be produced by ordinary synthetic chemistry techniques.
  • the compound (1) of the present invention and the starting compounds (2), (7) and the like may have optically active isomers in addition to a number of tautomeric forms such as those shown below. May exist. All such forms are included in the scope of the present invention.
  • the target compound can be obtained by subjecting the compound of the present invention to a usual post-treatment after the reaction.
  • the structure of the compound of the present invention was determined from IR, NMR, MS and the like. Representative examples of the compound of the present invention are shown in Tables 1 and 2.
  • the herbicide of the present invention contains one or more of the compounds of the present invention as an active ingredient.
  • the compound of the present invention can be used in a pure form without adding other components, or in a form that can be taken by a general pesticide for the purpose of using it as a pesticide, ie, hydrating agents, granules. It can be used in the form of powders, powders, emulsions, aqueous solvents, suspensions, flowables, etc.
  • solid additives are used as additives and carriers, plant powders such as soybean flour and barley flour, diatomaceous earth, apatite, gypsum, talc, bentonite, pyrophyllite, clay, etc.
  • Organic and inorganic compounds such as mineral fine powder, sodium benzoate, urea and sodium sulfate are used.
  • petroleum fractions such as kerosene, xylene and sorbent naphtha, cyclohexane, cyclohexanone, DMF, DMS0, alcohol, acetate, trichloroethylene, methylisobutyl butyl
  • surfactants can be added, if necessary, to obtain a uniform and stable form in these preparations.
  • the surfactant is not particularly limited.
  • the surfactant examples include alkylphenyl ether to which polyoxyethylene is added, alkyl ether to which polyoxyethylene is added, higher fatty acid ester to which polyoxyethylene is added, and polyoxyethylene.
  • Nonionic surfactants such as added sorbynyl higher fatty acid esters, polyoxyethylene-added tristylylphenyl ether, etc., sulfate esters of alkylphenyl ethers added with polyoxyethylene, alkylbenzene sulfonates , Higher alcohol sulfates, alkyl sulfates, alkyl naphthalene sulfonates, polycarboxylates, lignin sulfonates, formaldehyde condensates of alkyl naphthalene sulfonates, isobutylene-maleic anhydride Heavy And the like.
  • the active ingredient concentration in the herbicide of the present invention varies depending on the form of the preparation described above.
  • a wettable powder 5 to 90% by weight (hereinafter simply referred to as%), preferably 10 to 85%:
  • a concentration of 0.01 to 50%, preferably 0.05 to 40% is used.
  • the wettable powder and emulsion thus obtained are diluted to a predetermined concentration with water to form a suspension.
  • the granules are directly sprayed or mixed before or after germination of the weeds.
  • an appropriate amount of 0.1 g or more of the active ingredient is applied per hectare.
  • the herbicide of the present invention can be used by mixing with known fungicides, insecticides, acaricides, herbicides, plant growth regulators, fertilizers, and the like.
  • synergistic action of the mixed drugs can be expected to have even higher effects. 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 anilide herbicides such as diflufenican and propanil, and mouth-lowacetarilide herbicides such as arachlor and pretilachlor, and 2,4-D , 2, 4 —
  • Aryloxy alkanoic acid herbicides such as DB, aryloxy phenoxy alkanoic acid herbicides such as diclohop-methyl, phenoxaprop-ethyl, alkaryl carboxylic acids such as dicampa, pyrithiobac Acid herbicides, imidazolinone herbicides such as imazaquin and imazethapyr, urea herbicides such as didurone and isoprolone, carbamate herbicides such as chlorprofam and phenmedifam, and thiocarbamate such as tiobencalp and EPTC.
  • anilide herbicides such as diflufenican and propanil
  • Triazinone herbicides triazine herbicides such as atrazine and cyanadine; triazopyrimidine herbicides such as flumeram; ditribyl herbicides such as promoxinil and diclobenyl; glyphosate Phosphoric acid herbicides such as glyphosinate, quaternary ammonium salt herbicides such as paracoat and difuenzo coat, and cyclic imid herbicides such as flumichlorack-pentyl and fluthiacet-methyl , And others, isoxavene, ethomethate, oxaziazone, kink mouth rack, Romazon, Surco preparative Rio down, Shinmechiri down, Jichiopiru, Pirazore DOO, Piride DOO, Furupokisamu, base down evening Zon, Benfuruse one preparative, further cell Tokishijimu, like Kisanjion herbicides to cyclo such tralkoxydim. Also, a
  • Table 4 shows the NMR data of the synthesized compounds in Table 3.
  • Solvent Bok NMR-4 is, ⁇ 5 6 -DMSO, others, CDC1 3.
  • n-io 1.4 (s, 6H), 2.5 (s, 2H), 3.1 (s, 3H), 3.3 (s, 3H), 3.5 (s, 3H), thigh-53.8 (t, 2H) ), 4.4 (t, 2H), 7.l (d, 1H), 8.1 (d, 1H)
  • IK-33 1.4 (s, 6H), 2.0 (s, 3H), 2.5 (s, 2H), 3.25 (s, 3H), 4.5 (s, 3H) Thigh-16 5.9 (s, lH), T.5 (d, lH), 8.1 (d, 1H)
  • Parts in Formulation Examples are parts by weight.
  • Example 2 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 ground, and then granulated into granules having a diameter of 0.5 to 1.0 mm to obtain granules having an active ingredient of 5%.
  • the compound of the present invention shows a high herbicidal activity under any conditions of upland crops, in any of soil treatment and foliage treatment, and shows high efficacy against various kinds of upland weeds such as ichibi, inubu, akinoenokorogosa, and wild oats. Also, corn, wheat, barley and other barley, soybeans, potatoes and other crop-selective compounds are also included.
  • the compound of the present invention also includes a compound having a plant growth regulating effect, such as for producing growth suppression, on useful plants such as crops, ornamental plants, and fruit trees.
  • the compound of the present invention has excellent herbicidal activity against paddy weeds such as Nobie, Tamagayari, Omodaka and Hotaru, and has selectivity for 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 also include those having fungicidal activity, insecticidal and acaricidal activity. Next, test examples relating to the effect of the herbicide of the present invention will be shown.
  • the herbicidal effect was investigated according to the following criteria and expressed as a herbicidal index.
  • the numbers 1, 3, and 5.9 are 0 and 2, 2 and 4, 4 and 6, 6 and 8, respectively.
  • the compound of the present invention can be industrially advantageously synthesized, is suitable as a herbicide for controlling weeds such as corn, and is industrially useful.

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  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Environmental Sciences (AREA)
  • Zoology (AREA)
  • Plant Pathology (AREA)
  • Wood Science & Technology (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)

Abstract

L'invention porte sur des dérivés de la pipéridinedione (ou leurs sels) de formule générale (1) dans laquelle: R1 et R2 représentent chacun halogéno, C¿1-6? alkyle, C1-6 alkylsulfonyle, etc.; R?3¿ représente halogéno, C¿1-6? alkyle, etc.; n est 0, 1 ou 2; R?4 et R5¿ représentent chacun hydrogène, C¿1-6? alkyle, etc.; R?6 et R7¿ représentent chacun C¿1-6? alkyle ou peuvent être liés l'un à l'autre pour former une chaîne alkylène; R?8¿ représente hydrogène, C¿1-6? alkyle, etc.; et Z représente amino, phényle, hétérocycle, etc. facultativement substitués. L'invention porte également sur un herbicide contenant un ou plusieurs de ces constituants.
PCT/JP2000/001062 1999-02-26 2000-02-24 Derives substitues de la piperidinedione et herbicide WO2000050397A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AU26911/00A AU2691100A (en) 1999-02-26 2000-02-24 Substituted piperidinedione derivatives and herbicide
JP2000600980A JP4597379B2 (ja) 1999-02-26 2000-02-24 置換ピペリジンジオン誘導体および除草剤

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP11/49415 1999-02-26
JP11049415A JP2000247953A (ja) 1999-02-26 1999-02-26 置換ピペリジンジオン誘導体および除草剤

Publications (1)

Publication Number Publication Date
WO2000050397A1 true WO2000050397A1 (fr) 2000-08-31

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JP (2) JP2000247953A (fr)
AU (1) AU2691100A (fr)
WO (1) WO2000050397A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003106403A1 (fr) * 2002-06-13 2003-12-24 Bayer Healthcare Ag Derives de carboxamides
US8765735B2 (en) 2009-05-18 2014-07-01 Infinity Pharmaceuticals, Inc. Isoxazolines as inhibitors of fatty acid amide hydrolase
US8927551B2 (en) 2009-05-18 2015-01-06 Infinity Pharmaceuticals, Inc. Isoxazolines as inhibitors of fatty acid amide hydrolase
US9149465B2 (en) 2009-05-18 2015-10-06 Infinity Pharmaceuticals, Inc. Isoxazolines as inhibitors of fatty acid amide hydrolase

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0641780A1 (fr) * 1991-07-09 1995-03-08 Nippon Soda Co., Ltd. Derive de cyclohexanedione heterocyclique, production de celui-ci, et herbicide
JPH07206863A (ja) * 1994-01-13 1995-08-08 Nippon Soda Co Ltd 置換縮合ピペリジンジオン誘導体および除草剤
JPH08183701A (ja) * 1994-12-28 1996-07-16 Nippon Soda Co Ltd 置換ピペリジンジオン誘導体および除草剤
WO1998029421A1 (fr) * 1996-12-30 1998-07-09 Monsanto Company Hydrogenation de melanges de cyanophosphonates et de glycine

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Publication number Priority date Publication date Assignee Title
US4808720A (en) * 1986-06-09 1989-02-28 Stauffer Chemical Company Certain 3-benzoyl-4-oxolactams
AU5340098A (en) * 1996-12-27 1998-07-31 Nippon Soda Co., Ltd. Substituted piperidinedione derivatives and herbicides

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0641780A1 (fr) * 1991-07-09 1995-03-08 Nippon Soda Co., Ltd. Derive de cyclohexanedione heterocyclique, production de celui-ci, et herbicide
JPH07206863A (ja) * 1994-01-13 1995-08-08 Nippon Soda Co Ltd 置換縮合ピペリジンジオン誘導体および除草剤
JPH08183701A (ja) * 1994-12-28 1996-07-16 Nippon Soda Co Ltd 置換ピペリジンジオン誘導体および除草剤
WO1998029421A1 (fr) * 1996-12-30 1998-07-09 Monsanto Company Hydrogenation de melanges de cyanophosphonates et de glycine

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003106403A1 (fr) * 2002-06-13 2003-12-24 Bayer Healthcare Ag Derives de carboxamides
US8765735B2 (en) 2009-05-18 2014-07-01 Infinity Pharmaceuticals, Inc. Isoxazolines as inhibitors of fatty acid amide hydrolase
US8927551B2 (en) 2009-05-18 2015-01-06 Infinity Pharmaceuticals, Inc. Isoxazolines as inhibitors of fatty acid amide hydrolase
US9149465B2 (en) 2009-05-18 2015-10-06 Infinity Pharmaceuticals, Inc. Isoxazolines as inhibitors of fatty acid amide hydrolase

Also Published As

Publication number Publication date
AU2691100A (en) 2000-09-14
JP4597379B2 (ja) 2010-12-15
JP2000247953A (ja) 2000-09-12

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