WO1998035964A1 - Benzoxazinyl-heterocycles a activite herbicide - Google Patents

Benzoxazinyl-heterocycles a activite herbicide Download PDF

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Publication number
WO1998035964A1
WO1998035964A1 PCT/EP1998/000651 EP9800651W WO9835964A1 WO 1998035964 A1 WO1998035964 A1 WO 1998035964A1 EP 9800651 W EP9800651 W EP 9800651W WO 9835964 A1 WO9835964 A1 WO 9835964A1
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Prior art keywords
general formula
group
branched
linear
same meanings
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PCT/EP1998/000651
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English (en)
Inventor
Giovanni Meazza
Franco Bettarini
Piero La Porta
Sergio Massimini
Ernesto Signorini
Domenico Portoso
Original Assignee
Isagro Ricerca S.R.L.
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Publication of WO1998035964A1 publication Critical patent/WO1998035964A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—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 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
    • A01N43/72—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
    • A01N43/84—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 six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
    • C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
    • C07D265/36—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings condensed with one six-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems

Definitions

  • the present invention relates to benzoxazinyl- heterocycles .
  • the present invention relates to benzoxazinyl-heterocycles having a high herbicidal activity, a process for their preparation and their use as herbicides for the control of weeds in agricultural crops.
  • Benzoxazinyl-heterocycles having a herbicidal activity are described, among others, in U.S. patents 4.640.707, 4.761.174, 4.798.620, 4.877.444 and 4.902.335.
  • U.S. patent 4.640.707 describes the compound corresponding to N- (7-fluoro-3 , 4-dihydro-3- oxo-4-prop-2-inyl-2H-l , 4—benzoxazin-6-yl) cyclohex-1- ene-1, 2-dicarboximide.
  • This product when applied in post-emergency, is highly phytotoxic with respect to all the most important agricultural crops and cannot therefore be used in the above applications.
  • X represents a hydrogen atom; a fluorine atom or a chlorine atom;
  • R represents a group having general formula (II) :
  • R, R 1 and R- represent a hydrogen atom; or a C j -C- alkyl or haloalkyl group, linear or branched;
  • R 3 , R 4 , R 5 , R 6 and R- represent a hydrogen atom; or a C ⁇ C ⁇ alkyl or haloalkyl group, linear or branched;
  • X 1 and X- represent a hydrogen atom; a C,-C 4 alkyl or haloalkyl group, linear or branched; a C,-C 4 alkoxyl or haloalkoxyl group, linear or branched;
  • E represents one of the following heterocyclic groups represented by the following general formulae E 1 - E 10 :
  • R b represents a C.,-C 3 alkyl group, linear or branched
  • R 8 and R 9 represent a
  • R 10 and R n represent a hydrogen atom; a C 1 -C 6 alkyl group, linear or branched; a C 3 -C 6 cycloalkyl group; a C 3 -C 5 alkenyl group, linear or branched; a C 3 -C 5 alkinyl group, linear or branched; or R 10 and
  • R jointly represent a C--C 5 alkylene or oxyalkylene chain, linear or branched; r represents 1 or 2 ; s represents an integer between 0 and 2 , extremes included.
  • the benzoxazinyl-heterocycles having general formula (I) have a high herbicidal activity.
  • a further object of the present invention relates to processes for the preparation of the compounds having general formula (I) .
  • the compounds having general formula (I) wherein E represents an E 1 group, corresponding to the following general formula (1-1) :
  • the above reaction can be carried out without or in the presence of an inert organic solvent, at a temperature ranging from room temperature to the boiling point of the solvent possibly used, preferably between 60 °C and 200 °C, optionally in the presence of a catalyst.
  • Inert organic solvents which can be used for the purpose are, for example, benzene, toluene, xylene, chlorobenzene, acetic acid, diisopropylether, dimetho- xyethane, tetrahydrofuran, dioxane.
  • Catalysts which can be used for the purpose are, for example, mixtures of nitrogenated organic bases such as, for example, triethylamine, piperidine, pyrrolidine, with aliphatic carboxylic acids such as, for example, acetic acid, propionic acid, butyrric acid.
  • nitrogenated organic bases such as, for example, triethylamine, piperidine, pyrrolidine
  • aliphatic carboxylic acids such as, for example, acetic acid, propionic acid, butyrric acid.
  • Anhydrides having general formula (IV) are compounds which are known in literature.
  • the aminobenzoxazinones having general formula (V) can be prepared according to the known methods.
  • X, R, R 1 , R 2 and R 8 have the same meanings defined above, can be prepared by reacting with a cyclizing agent such as, for example, phosgene or trichloromethylchloroformiate, a hydrazide having general formula (VI) :
  • the above reaction can be carried out by treating the hydrazide having general formula (VI) , dissolved or suspended in a suitable inert organic solvent, with the cyclizing agent, optionally dissolved in turn in a suitable inert organic solvent, at a temperature ranging from 20 °C to the boiling point of the reaction mixture, possibly in the presence of an organic or inorganic base.
  • inert organic solvents which can be used for the purpose are, for example, methylene chloride, chloroform, 1, 2-dichloroethane, benzene, toluene, xylene, chlorobenzene, ethyl ether, tetrahydrofuran, dioxane, ethyl acetate.
  • Inorganic bases which can be used for the purpose are, for example, sodium bicarbonate, sodium carbonate, potassium carbonate.
  • Organic bases which can be used are, for example, triethyla ine, pyridine, 4-dimethylaminopyridine.
  • the hydrazides having general formula (VI) can be prepared by converting the a inobenzoxazinones having general formula (V) described above into the corresponding hydrazides having general formula (VII) :
  • R-X' (X) wherein R has the same meanings described above and X' represents a halogen atom, preferably chlorine or bromine, or an R'SO-0 group wherein R' represents a C 1 -C 4 alkyl or haloalkyl group, linear or branched, or a phenyl group possibly substituted with C ⁇ -C j alkyl groups, linear or branched, with nitro groups, or with halogen atoms such as bromine, chlorine and fluorine.
  • X' represents a halogen atom, preferably chlorine or bromine, or an R'SO-0 group wherein R' represents a C 1 -C 4 alkyl or haloalkyl group, linear or branched, or a phenyl group possibly substituted with C ⁇ -C j alkyl groups, linear or branched, with nitro groups, or with halogen atoms such as bromine, chlorine and fluorine.
  • the above reaction can be advantageously carried out in an inert organic solvent and in the presence of an inorganic base, at a temperature ranging from -10 °C to the boiling point of the solvent used.
  • Inert organic solvents which can be used for the purpose are benzene, toluene, xylene, di ethoxyethane, diisopropylether, tetrahydrofuran, dioxane, acetoni- trile, N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone, dimethylsulfoxide.
  • Inorganic bases which can be used for the purpose are, for example, hydroxides and carbonates of sodium, potassium and calcium, sodium hydride, sodium metho- xide.
  • benzoxazinyl derivatives having general formulae (IX-3) , (IX-4) and (IX-5) and the compounds having general formula (X) can be prepared according to the methods known in literature.
  • R represents a C 1 -C 4 alkyl group, linear or branched.
  • the above reaction is preferably carried out in an inert organic solvent, in the presence of an organic or inorganic base, at a temperature ranging from room temperature to the boiling point of the reaction mixture.
  • Inert organic solvents which can be used for the purpose are, for example, benzene, toluene, xylene, dimethoxyethane, diisopropylether, tetrahydrofuran, dioxane, acetonitrile, N,N-dimethylformamide, N,N- dimethylacetamide, N-methylpyrrolidone, dimethylsulfoxide.
  • Organic bases which can be used are, for example, triethylamine, pyridine, 4- (N,N-dimethylamine)pyridine, alkoxides of alkaline metals such as, for example, sodium ethoxide, sodium ethoxide, potassium t-butoxi- de, salts of carboxylic acids such as, for example, sodium acetate, potassium acetate.
  • Inorganic bases which can be used for the purpose are, for example, sodium hydride, potassium hydride, sodium carbonate, potassium carbonate, sodium hydoxide, potassium hydroxide.
  • the intermediate having general formula (XI) can be prepared by the reaction of an arylisocyanate having general formula (XII) :
  • the arylisocyanates having general formula (XII) can in turn be prepared by the reaction of an a inoben- zoxazinone having general formula (V) described above with phosgene or trichloromethylformiate, operating according to processes known in the art.
  • E represents an E- group, corresponding to the following general formula
  • Inert organic solvents which can be used for the purpose are, for example, ethyl ether, tetrahydrofuran, dioxane, methylene chloride, chloroform, ethyl acetate.
  • Organic bases which can be used are, for example, triethylamine, pyridine, 4-dimethylaminopyridine.
  • Inorganic bases which can be used are, for example, sodium bicarbonate, sodium carbonate, potassium carbonate .
  • the cyclization reaction of the intermediate having general formula (XVI) is carried out in the presence of an inert organic solvent, an oxidating agent and an acid acceptor, at a temperature ranging from -30°C to +30°C.
  • Inert organic solvents which can be used for the purpose are, for example, methylene chloride, chloroform, chlorobenzene, N,N-dimethylformamide, ethyl acetate.
  • Oxidating agents which can be used are, for example, bromine, chlorine, sodium hypochlorite.
  • Acid acceptors which can be used for the purpose are, for example, organic bases such as, for example, triethylamine, pyridine, dimethylaniline, or inorganic bases such as, for example, sodium hydroxide, potassium carbonate, calcium carbonate.
  • organic bases such as, for example, triethylamine, pyridine, dimethylaniline
  • inorganic bases such as, for example, sodium hydroxide, potassium carbonate, calcium carbonate.
  • (XIV) can in turn be prepared by the reaction of an aminobenzoxazinone having general formula (V) described above with phosgene or trichloromethylformiate, operat- ing according to processes known in the art.
  • reaction is carried out by treating the compound having general formula (XVII), dissolved or suspended in a suitable inert organic solvent, with phosgene or trichloromethylchloroformiate, possibly dissolved in turn in a suitable inert organic solvent, at a temperature ranging from 20 °C to the boiling point of the reaction mixture, optionally in the presence of an organic or inorganic base.
  • Inert organic solvents which can be used for the purpose are, for example, methylene chloride, chloroform, 1, 2-dichloroethane, benzene, toluene, xylene, chlorobenzene, ethyl ether, tetrahydrofuran, dioxane, ethyl acetate.
  • Organic bases which can be used are, for example, triethylamine, pyridine, 4-dimethylaminopyridine.
  • Inorganic bases which can be used are, for example, sodium bicarbonate, sodium carbonate, potassium carbonate.
  • the compounds having general formula (XVII) can in turn be prepared by the reaction of an arylisothiocya- nate having general formula (XIV) described above with a compound having general formula (XVIII) :
  • the reaction is carried out by treating the compound having general formula (XIX) , dissolved or suspended in a suitable inert organic solvent, with phosgene or trichloromethylchloroformiate, possibly dissolved in turn in a suitable inert organic solvent, at a temperature ranging from 20 °C to the boiling point of the reaction mixture, optionally in the presence of an organic or inorganic base.
  • Inert organic solvents which can be used for the purpose are, for example, methylene chloride, chloroform, 1 , 2-dichloroethane, benzene, toluene, xylene, chlorobenzene, ethyl ether, tetrahydrofuran, dioxane, ethyl acetate.
  • Organic bases which can be used are, for example, triethylamine, pyridine, 4-dimethylaminopyridine.
  • Inorganic bases which can be used are, for example, sodium bicarbonate, sodium carbonate, potassium carbonate.
  • the compounds having general formula (XIX) can in turn be prepared by the reaction of an arylisocyanate having general formula (XII) described above with a compound having general formula (XVIII) described above, operating according to processes known in the art.
  • the compounds having general formula (I) wherein E represents an E 10 group, corresponding to the following general
  • R 11 wherein R 10 and R n have the same meanings described above.
  • the reaction is carried out in an inert organic solvent, at a temperature ranging from 0°C to the boiling point of the solvent used, possibly in the presence of an organic or inorganic base as catalyst.
  • inert organic solvents which can be used for the purpose are, for example, methylene chloride, chloroform, carbon tetrachloride, chlorobenzene, benzene, toluene, xylene, hexane, octane, cyclohexane, ethyl ether, tetrahydrofuran, di ethoxyethane, acetone, methylethylketone, acetonitrile, ethyl acetate, dimethylformamide .
  • Organic bases which can be used are, for example, triethylamine, pyridine.
  • Inorganic bases which can be used are, for exam- pie, sodium carbonate, potassium carbonate.
  • Specific examples of benzoxazinyl-heterocycles having general formula (I) which are interesting for their herbicidal activity are indicated in Tables 1-10 below.
  • the compounds having general formula (I) of the present invention have shown a high herbicidal activity which makes them suitable for use in the agrarian field to defend crops from weeds.
  • the compounds having general formula (I) are effective in the control, both in pre- and post-emergency, of numerous monocotyledon and dicotyledon weeds. At the same time, these compounds have compatibility or no toxic effects with respect to useful crops, both in pre-emergency and post-emergency treatment.
  • Examples of weeds which can be efficiently controlled using the compounds having general formula (I) of the present invention are: Abutilon theofrasti, Amaranthus retroflexus, Capsella bursa pastoris, Chenopodium album, Convolvulus sepium, Galium aparine. Geranium dissecturo, Ipomea sp. , Matricaria chamomilla, Papaver rhoaes, Phaseolus aureus , Polvgonum persicaria, Portulaca oleracea, Sida spinosa, Solanum nicrrum, Stellaria media, Veronica persica, Xanthium sp. , etc.
  • a further object of the present invention relates to a method for controlling weeds in cultivated areas, by the application of the compounds having general formula (I) .
  • the quantity of compound to be applied to obtain the desired effect can vary in relation to different factors such as, for example, the compound used, the crop to be preserved, the weed to be fought against, the degree of infestation, the climatic conditions, the characteristics of the soil, the method of application, etc.
  • compositions with a herbicidal activity containing, as active substance, one or more compounds having general formula (I) , possibly also as a mixture of isomers.
  • Compositions can be used in the form of dry powders, wettable powders, emulsifiable concentrates, microemulsions , pastes, flakes, solutions, suspensions, etc.: the selection of the type of composition depends on the specific use.
  • compositions are prepared according to the known methods, for example by diluting or dissolving the active substance with a solvent medium and/or solid diluent, optionally in the presence of surface-active agents.
  • Solid inert diluents, or carriers which can be used are kaolin, alumina, silica, talc, bentonite, chalk, quartz, dolomite, attapulgite, mont orillonite, diatomaceous earth, cellulose, starch, etc.
  • Liquid inert diluents in addition to water of course, which can be used are organic solvents such as aromatic hydrocarbons (xylols, mixtures of alkylben- zols, etc.), aliphatic hydrocarbons (hexane, cyclohexa- ne, etc.), halogenated aromatic hydrocarbons (chloro- benzol, etc.), alcohols (methanol, propanol, butanol, octanol, etc.), esters (isobutyl acetate, etc.), ketones (acetone, cyclohexanone, acetophenone, isopho- rone, ethylamylketone, etc.), or vegetable or mineral oils or their mixtures, etc.
  • organic solvents such as aromatic hydrocarbons (xylols, mixtures of alkylben- zols, etc.), aliphatic hydrocarbons (hexane, cyclohexa-
  • Surface-active agents which can be used are wetting and emulsifying agents of the non-ionic type (polyethoxylated alkylphenols , polyethoxylated fatty alcohols, etc.), anionic type (alkylbenzenesulfonates , alkylsulfonates , etc.), cationic type (quaternary salts of alkylammonium, etc.).
  • non-ionic type polyethoxylated alkylphenols , polyethoxylated fatty alcohols, etc.
  • anionic type alkylbenzenesulfonates , alkylsulfonates , etc.
  • cationic type quaternary salts of alkylammonium, etc.
  • dispersing agents for example lignin and its salts, derivatives of cellulose, alginates, etc.
  • stabilizers for example antioxi- dants, ultraviolet ray absorbers, etc.
  • active ingredients such as, for example, other herbicides, fungicides, insecticides or acaricides, fertilizers.
  • the concentration of active substance in the above compositions can vary within a wide range, depending on the active compound, the applications for which it is destined, the environmental conditions and the type of formulation adopted.
  • the concentration of active substance is between 1% and 90%, preferably between 5% and 50%.
  • the following examples are provided for illustrative purposes and do not limit the scope of the present invention.
  • EXAMPLE 1 Preparation of N- [7-fluoro-3,4-dihydro- (4-methoxybut-2- inyl) -3-oxo-2H-l, 4-benzoxazin-6-yl] cyclo-hex-l-ene-1,2- dicarboxyimide (Compound Nr. 1) .
  • the solid obtained is then purified by silica gel chromatography eluating with hexane/ethyl acetate in a ratio fo 2:1.
  • the herbicidal activity of Compound Nr . 1 was evaluated in post-emergency treatment and was compared with the herbicidal activity of N- (7-fluoro-3 , 4-dihy- dro-3-oxo-4-prop-2-inyl-2H-l, 4—benzoxazin-6-yl) cyclo- hex-l-ene-1 , 2-dicarboxyimide (RC) corresponding to Compound Nr. 20 of U.S. patent 4.640.707.
  • Vases (diameter of more than 10 cm, height 10 cm) containing sandy earth were prepared. In each of these one of the following weeds was planted together with the following crops (10 vases for each species) : weeds (dicotyledons) : Abutilon theofrasti (AT) , Convolvulus sepium (CS) , Ipomea purpurea (IP) ; crops: Zea mays (maize) , Glycine max (soybean) . Water was added to each vase in a suitable quantity for a good germination of the seeds. The vases were divided into two groups each containing 5 vases for each weed or crop.
  • the first group of vases was treated with a hydroaceto- ne dispersion of the two products under examination (Compound Nr. 1 and Compound RC) , acetone at 10% by volume and Tween 20 at 0.5%.
  • the second group was only treated with a hydroace- tone solution containing acetone at 10% by volume and Tween 20 at 0.5%, and was used as a comparison (blank) .
  • All the vases were kept under observation in a conditioned environment under the following environmental conditions: temperature: 24 °C; relative humidity: 60%; - photoperiod: 16 hours; luminous intensity: 10000 lux.
  • each data is the average of at least 5 tests
  • (b) the letters indicate the weeds listed above.

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (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)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

La présente invention concerne des benzoxazinyl-hétérocycles de formule générale (I). Lesdits benzoxazinyl-hétérocycles présentent une forte activité herbicide.
PCT/EP1998/000651 1997-02-12 1998-02-04 Benzoxazinyl-heterocycles a activite herbicide WO1998035964A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ITMI97A000275 1997-02-12
ITMI970275 IT1289618B1 (it) 1997-02-12 1997-02-12 Benzossazinil-eterocicli ad attivita' erbicida

Publications (1)

Publication Number Publication Date
WO1998035964A1 true WO1998035964A1 (fr) 1998-08-20

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Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0176101A1 (fr) * 1984-09-27 1986-04-02 Sumitomo Chemical Company, Limited Triazolopyridazines, leur préparation et leur utilisation
US4640707A (en) * 1984-07-23 1987-02-03 Sumitomo Chemical Company, Ltd. Tetrahydrophthalimides and their herbicidal use
US4761174A (en) * 1987-04-14 1988-08-02 Fmc Corporation Triazolin-5-one herbicides
US4798620A (en) * 1986-09-06 1989-01-17 Nihon Tokushu Noyaku Seizo K.K. Benzoxazines and herbicidal use
EP0328001A1 (fr) * 1988-02-05 1989-08-16 Sagami Chemical Research Center Composés de benzoxazinone et composition herbicide les contenant
DE3832348A1 (de) * 1988-03-10 1989-09-28 Bayer Ag Substituierte benzoxazinone, mehrere verfahren sowie neue zwischenprodukte zu ihrer herstellung sowie ihre herbizide verwendung
EP0338533A2 (fr) * 1988-04-20 1989-10-25 Sumitomo Chemical Company, Limited N-Phénylimides, leur préparation et utilisation
WO1995022547A1 (fr) * 1994-02-16 1995-08-24 E.I. Du Pont De Nemours And Company Heterocycles tricycliques et urees bicycliques herbicides
EP0683160A1 (fr) * 1994-04-04 1995-11-22 Sumitomo Chemical Company, Limited Dérivés d'iminothiazolin et herbicides contenant ces dérivés comme principes actifs
DE4424787A1 (de) * 1994-07-14 1996-01-18 Bayer Ag Substituierte Aryliminoheterocyclen

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4640707A (en) * 1984-07-23 1987-02-03 Sumitomo Chemical Company, Ltd. Tetrahydrophthalimides and their herbicidal use
EP0176101A1 (fr) * 1984-09-27 1986-04-02 Sumitomo Chemical Company, Limited Triazolopyridazines, leur préparation et leur utilisation
US4798620A (en) * 1986-09-06 1989-01-17 Nihon Tokushu Noyaku Seizo K.K. Benzoxazines and herbicidal use
US4761174A (en) * 1987-04-14 1988-08-02 Fmc Corporation Triazolin-5-one herbicides
EP0328001A1 (fr) * 1988-02-05 1989-08-16 Sagami Chemical Research Center Composés de benzoxazinone et composition herbicide les contenant
DE3832348A1 (de) * 1988-03-10 1989-09-28 Bayer Ag Substituierte benzoxazinone, mehrere verfahren sowie neue zwischenprodukte zu ihrer herstellung sowie ihre herbizide verwendung
EP0338533A2 (fr) * 1988-04-20 1989-10-25 Sumitomo Chemical Company, Limited N-Phénylimides, leur préparation et utilisation
WO1995022547A1 (fr) * 1994-02-16 1995-08-24 E.I. Du Pont De Nemours And Company Heterocycles tricycliques et urees bicycliques herbicides
EP0683160A1 (fr) * 1994-04-04 1995-11-22 Sumitomo Chemical Company, Limited Dérivés d'iminothiazolin et herbicides contenant ces dérivés comme principes actifs
DE4424787A1 (de) * 1994-07-14 1996-01-18 Bayer Ag Substituierte Aryliminoheterocyclen

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IT1289618B1 (it) 1998-10-15

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