WO2002070476A1 - Phenylpyrroles presentant une activite herbicide - Google Patents

Phenylpyrroles presentant une activite herbicide Download PDF

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Publication number
WO2002070476A1
WO2002070476A1 PCT/EP2002/002297 EP0202297W WO02070476A1 WO 2002070476 A1 WO2002070476 A1 WO 2002070476A1 EP 0202297 W EP0202297 W EP 0202297W WO 02070476 A1 WO02070476 A1 WO 02070476A1
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WO
WIPO (PCT)
Prior art keywords
group
dichloro
chloro
methyl
trifluoromethylpyrrol
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PCT/EP2002/002297
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English (en)
Inventor
Franco Bettarini
Giovanni Meazza
Paolo Castoro
Domenico Portoso
Piero La Porta
Original Assignee
Isagro Ricerca S.R.L.
SAPINO, Paola
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Application filed by Isagro Ricerca S.R.L., SAPINO, Paola filed Critical Isagro Ricerca S.R.L.
Publication of WO2002070476A1 publication Critical patent/WO2002070476A1/fr

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    • 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
    • C07D401/14—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 three or more hetero 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
    • A01N43/36—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
    • 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
    • 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
    • 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
    • C07D405/14—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 three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings

Definitions

  • the present invention relates to new phenylpyrroles. More specifically, the present invention relates to new phenylpyrroles having a high herbicidal activity, the processes for their preparation and their use as herbicides for controlling weeds in agricultural crops.
  • Phenylpyrroles with a herbicidal activity are described in European patent application EP 1061072.
  • the Applicant has now found new phenylpyrroles which, compared to the products described in the above patent, have improved characteristics in terms of herbicidal activity with respect to weeds and/or lower phyto- toxicity for crops of agrarian interest.
  • the object of the present invention therefore relates to new phenylpyrroles having general formula (I) :
  • R and R lf the same or different, represent a C ⁇ -C al ⁇ ky1 or haloalkyl group
  • - X and Xi represent a halogen atom
  • X 2 represents a hydrogen atom or a halogen atom
  • - Y represents a halogen atom, C ⁇ -C 4 haloalkyl or halo- alkoxyl group, a cyano group a nitro group;
  • - W represents one of the following groups:
  • R a and R b represent a hydrogen atom or a C ⁇ -C alkyl group
  • R 2 represents: C 3 -C6 alkenyl group optionally substituted by C1-C 4 alkoxyl groups; a C 3 -C6 alkinyl group optionally substituted by C1-C 4 alkoxyl groups; a C 2 -Ce alkoxyalkyl or alkylthioalkyl group optionally substituted by C1-C4 alkoxyl groups; a C 4 -C ⁇ o cycloalkylalkyl group optionally substituted by C ⁇ -C alkyl groups and optionally interrupted by oxygen atoms; a C 2 -C 8 alkyla- minoalkyl group or a C4-C 12 dialkylaminoalkyl group; a C5-C9 4-morpholylalkyl group; a C5-C9 1-pyrrolidylalkyl group; a C 6 -C ⁇ o 1-piperidylalkyl group; a C5-C9 2- pyrrolidinonylalkyl group;
  • R 3 represents a C3-C6 alkenyl or alkinyl group optionally substituted by C1-C4 alkoxyl groups and optionally halogenated; a C 2 -Ce alkoxyalkyl or alkylthioalkyl group optionally halogenated and optionally substi- tuted by C1-C4 alkoxyl groups; a C-C ⁇ 0 cycloalkylalkyl group optionally substituted by C1-C4 alkyl or haloalkyl groups, optionally halogenated and optionally interrupted by oxygen atoms; a C3-C8 alkylaminoalkyl group or a C4-C 12 dialkylaminoalkyl group optionally halogenated; a C-C 8 alkoxycarbonylalkyl group optionally halogenated; an OH group; a C ⁇ -C 6 alkoxyl or halo- alkoxyl group; a C 2 -C 7 alkylcarbonyl
  • Z represents an oxygen atom or a sulfur atom
  • - m represents an integer ranging from 1 to 4; n represents zero or 1;
  • - p represents 1 or 2;
  • - K represents an oxygen atom or an NR k group wherein: - R k represents a hydrogen atom, an OH group, a Ci-C ⁇ alkoxyl or haloalkoxyl group; a C 2 -C6 alkylcarbony- loxy group optionally halogenated; a C 3 -C 6 alkenyl or alkinyl group optionally substituted by C1-C4 alkoxyl or haloalkoxyl groups and optionally halogenated; a C 2 -C 8 alkoxyalkyl group optionally halogenated; a C3-C8 cycloalkyl or C4-C10 cycloalkylalkyl group optionally substituted by C1-C4 alkyl or haloalkyl groups, optionally halogenated and optionally interrupted by oxygen atoms; a C 3 -C 8 alkylaminoalkyl group or a C4-C1
  • R 3 can also represent a C 3 -C 8 cycloalkyl group optionally substituted by C1-C4 alkyl or haloalkyl groups, optionally halogenated and optionally interrupted by oxygen atoms; an aryl group or an arylalkyl group, said groups optionally substituted by C1-C4 alkyl or haloalkyl, alkoxyl or haloalkoxyl groups, by halogen atoms, nitro groups, cyano groups;
  • R 3 and R 4 can also jointly represent a C-C 7 alkylene chain optionally substituted by C1-C4 alkyl groups and optionally interrupted by oxygen atoms or by an NR group wherein:
  • - R 5 represents a hydrogen atom, a Ci-C ⁇ alkyl or haloalkyl group; a C 3 -C 6 alkenyl or haloalkenyl group, a C 3 -C 6 alkinyl or haloalkinyl group, a C 2 -C 8 alkoxyalkyl or haloalkoxyalkyl group, a C2-C7 alkylcarbonyl or ha- loalkylcarbonyl group; alternatively, the group and Y group can jointly represent a -N(R 6 ) OCCR 7 R 8 0- chain wherein: - R 6 represents a C3-C6 alkenyl or haloalkenyl group optionally substituted by C1-C4 alkoxyl or haloalkoxyl groups, a C3-C6 alkinyl or haloalkinyl group optionally substituted by C1-C4 alkoxyl or haloalkoxyl groups, a C 2
  • R 9 represents a C ⁇ -C 8 alkyl group, a C3-C6 alkenyl group optionally substituted by C1-C4 alkoxyl groups; a C3-C6 alkinyl group optionally substituted by C1-C 4 alkoxyl groups; a C 2 -C 8 alkoxyalkyl or alkylthioalkyl group op- tionally substituted by C ⁇ -C 4 alkoxyl groups; a C3-C8 cycloalkyl or C4-C10 cycloalkylalkyl group optionally substituted by C1-C 4 alkyl or haloalkyl groups, optionally halogenated and optionally interrupted by oxygen atoms; a C2-C 8 alkylaminoalkyl or C4-C12 dialkylaminoal- kyl group; a C5-C9 4-morpholylalkyl group; a C5-C9 1- pyrrolidylalkyl group; a
  • the pyrroles having general formula (I) have a high herbicidal activity.
  • Specific examples of compounds having general for- mula (I) which are interesting for their activity are:
  • 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 W represents Wi, W 2 or W 4 can be prepared by the condensation of phenylpyrrole having general formula (II) with an alcohol, an amine or a thio-alcohol having general for- mula (III), to give an ester, an amide, or a thioester having general formula (la) according to reaction scheme
  • - A represents a LOC [ (CR a R b ) m ] n _ group wherein R a , R b , m and n have the meanings defined above, L represents a halogen atom or an OH group;
  • R 2 - Q represents an R 2 0 group-, an R 3 N(R 4 )- group or an R 9 S- group wherein R 2 , R 3 , R 4 and R 9 have the meanings defined above;
  • Wa represents a Wi group, a W 2 group or a W 4 group as defined above.
  • reaction represented in scheme 1 can be carried out according to the various operating procedures described in chemical literature for the preparation of esters, amides and thioesters by the condensation of acyl chlorides or carboxylic acids with alcohols and primary or secondary amines or with thioalcohols (see, for example: J. March, "Advanced Organic Chemistry", 4 th edition, John Wiley & Sons, New York and references indicated therein) .
  • the reaction with an alcohol, amine or thioalcohol having general formula (III) is preferably carried out in one or more inert solvents, in the presence of an organic or inorganic base, at a temperature ranging from -20°C to the boiling point of the reaction mixture.
  • solvents which can be used for the above reaction comprise water, aliphatic or cycloaliphatic hydrocarbons (petroleum ether, hexane, cyclohexane, etc.), chlorinated hydrocarbons (methylene chloride, chloroform, carbon tetrachloride, dichloroethane, etc.), aromatic hydrocarbons (benzene, toluene, xylene, chlorobenzene, etc.), ethers (diethyl ether, diisopropyl ether, dimeth- oxyethane, dioxane, tetrahydrofuran, etc.), ketones (acetone, methylethylketone, methylpropylketone, methylisobu- tylketone, etc.), nitriles (acetonitrile, benzonitrile, etc.), aprotic dipolar solvents (dimethylformamide, dimethylacetamide, hexamethyl-phosphorot
  • Inorganic bases which can be used for the purpose are, for example, hydroxides, sodium and potassium car- bonates and bicarbonates .
  • Organic bases which can be used for the purpose are, for example, triethylamine, pyridine, 4- dimethylaminopyridine, diazabicyclo-octane (DABCO) , di- azabicylononene (DBN) , diazabicycloundecene (DBU) .
  • DABCO diazabicyclo-octane
  • DBN di- azabicylononene
  • DBU diazabicycloundecene
  • Qi represents an R 2 OOC (CR a R b ) m _ group, an R 3 N(R 4 )OC (CR a Rb)m- group, an (RgS) OC (CR a R b ) m - group or a group
  • R 2 , R 3 4, R9, Ra, Rb, K, m and p have the meanings defined above;
  • - Li represents a halogen atom, or an R L S0 2 0- group wherein R L represents a C1-C4 alkyl or haloalkyl group or a phenyl group optionally substituted by C ⁇ -C 4 alkyl groups;
  • the reaction between the compounds having general formula (IV) and the compounds having general formula (V) is preferably carried out in the presence of one or more inert organic solvents and in the presence of a base, preferably inorganic, at a temperature ranging from -10°C to the boiling point of the reaction mixture.
  • Organic solvents which can be used for the purpose are, for example, aromatic hydrocarbons (benzene, toluene, xylene, chlorobenzene, etc.), ethers (diethyl ether, diisopropyl ether, dimethoxyethane, dioxane, tetrahydro- furan, etc.), alcohols and glycols (methanol, ethanol, methylcellosolve, ethylene glycol, etc.), ketones (acetone, methylethylketone, methylpropylketone, methylisobu- tylketone, etc.), nitriles (acetonitrile, benzonitrile, etc.), aprotic dipolar solvents (dimethylforma ide, di- methylacetamide, hexamethyl-phosphoro-triamide, dimethyl- sulfoxide, sulfolane, N-methylpyrrolidone, etc.).
  • aromatic hydrocarbons benzen
  • Inorganic bases which can be used for the purpose are, for example, hydrides, hydroxides and sodium and potassium carbonates.
  • the reaction can also be advantageously carried out in a biphasic system using as solvents water and an organic solvent immiscible therewith, in the presence of phase transfer catalysts, according to what is described by Dehmlow and Dehmlow in "Phase Transfer Catalysis” (1983), Verlag Chemie.
  • the compounds having general formula (I) wherein W and Y jointly represent an -N (R 6 ) OCCR 7 R 8 0- chain can be prepared starting from a pyrrolyl-aminophenol having formula (VI) by reaction with a compound having formula (VII) to give a pyrrolyl-benzoxazinone having general formula (Ic) ; this can be converted to the compounds having general formula (Id) by condensation with a compound having general formula (VIII) . This sequence of reactions is indicated in scheme 3.
  • - L 2 represents a halogen atom, an OH group, a C1-C4 alkoxyl group
  • L and L 4 represent a halogen atom or a RS0 2 0- group wherein R L represents a C1-C4 alkyl or haloalkyl group or a phenyl group optionally substituted by C1-C4 alkyl groups.
  • the reaction between a compound having general for- mula (VI) and a compound having general formula (VII) is preferably carried out in one or more inert organic solvents, in the presence of an organic or inorganic base in a molar ratio at least double with respect to the rea- gents, at a temperature ranging from -10°C to the boiling point of the reaction mixture.
  • Bases and solvents can be selected from those indicated as preferred for the reactions indicated in schemes 1 and 2.
  • reaction can also be advantageously carried out in a biphasic system using as solvents, water and an organic solvent immiscible therewith, in the presence of phase transfer catalysts, according to what is described in "Synthesis", 1984, pages 851-2.
  • reaction between a compound having formula (Ic) and a compound having formula (VIII) is carried out according to an operating procedure analogous to that described for the reaction indicated in scheme 2, in the presence of one or more inert organic solvents and in the presence of a base, at a temperature ranging from -10°C to the boiling point of the reaction mixture.
  • Bases and solvents can be selected from those indicated as preferred for the reactions specified in scheme 2. Also in this case the reaction can also be effected in a biphasic system using as solvents, water and an organic solvent immiscible therewith, in the presence of phase transfer catalysts.
  • the intermediates having general formulae (II), (IV) and (VI) when not described in European patent application EP 1061072, can be obtained according to the syn- thetic methods indicated therein.
  • the intermediates having general formulae (III), (V), (VII) and (VIII) are for the most part known or can be easily obtained according to methods known in organic chemical practice.
  • the compounds having general formula (I) have a high herbicidal activity which makes them suitable for use in the agrarian field to defend useful crops from weeds.
  • a further object of the present invention therefore relates to the use of the compounds having formula (I) as herbicides.
  • the compounds, object of the present invention are effective in the control, in both pre- emergence and post-emergence, of numerous monocotyledon and dicotyledon weeds. At the same time, these compounds show compatibility or absence of toxic effects with respect to crops useful in pre- and/or post-emergence treatment.
  • weeds which can be effectively controlled using the compounds having general formula (I) are: Abutilon theofrasti, Alisma plantago, Amaranthus spp., Amni maius, Capsella bursa pastoris, Chenopodium album, Convolvulus sepium, Galium aparine, Geranium dis- sectum, Ipomea spp., Matricaria spp., Papaver rhoaes, Phaseolus aureus, Polygonum persicaria, Portulaca olera- cea, Sida spinosa, Sinapsis arvensis, Solanum nigrum, Stellaria media, Veronica spp., Viola spp., Xanthium spp., Alopecurus myosuroides, Avena fatua, Cyperus spp., Digitaria sanguinalis, Echinocloa spp., Heleocaris avicu- laris, Heteranthera spp.
  • the above compounds have not shown any toxic effects towards any of the important agrarian crops such as rice (Oryza sativa) , wheat (Triticum sp. ) , barley (Hordeum vulgare) , maize (Zea mays) , soybean (Glycine max) .
  • 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 for obtaining the desired effect can vary in relation to various factors such as, for example, the compound used, the crop to be preserved, the weed to be destroyed, the degree of infestation, the climatic conditions, the characteristics of the ground, the application method, etc. Doses of compound ranging from 1 g to 1000 g per hectare generally provide sufficient control.
  • compositions with a herbicidal activity containing, as active substance, one or more compounds having general formula (I), also possibly as a mixture of isomers, together with solid carriers, liquid diluents, surface- active agents or other special additives.
  • compositions can be used, in the form of dry powders, wettable powders, emulsifiable concentrates, micro- emulsions, pastes, granulates, 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 and/or solid diluent medium, optionally in the presence of surface-active agents.
  • Kaolin alumina, silica, talc, bentonite, chalk, quartz, dolomite, attapulgite, montmorillonite, diato a- ceous earth, cellulose, starch, etc., can be used as solid inert diluents, or carriers.
  • Water, or organic solvents such as aromatic hydrocarbons (xylols, mixtures of alkylbenzols, etc.), aliphatic hydrocarbons (hexane, cyclohexane, etc.), halogenated aromatic hydrocarbons (chlorobenzol, etc.), alcohols (methanol, propanol, butanol, octanol, etc.), esters (isobutyl acetate, etc.), ketones (acetone, cyclo- hexanone, acetophenone, isophorone, ethylamylketone, etc.), or vegetable or mineral oils or their mixtures, etc., can be used as liquid inert diluents.
  • aromatic hydrocarbons xylols, mixtures of alkylbenzols, etc.
  • aliphatic hydrocarbons hexane, cyclohexane, etc.
  • halogenated aromatic hydrocarbons chlorobenzol
  • Wetting and emulsifying agents of the non-ionic type polyethoxylated alkylphenols, polyethoxylated fatty alcohols, etc.
  • of the anionic type alkylbenzenesul- fonates, alkylsulfonates, etc.
  • of the cationic type quaternary salts of alkylammonium, etc.
  • Dispersing agents for example lignin and its salts, derivatives of cellulose, alginates, etc.
  • stabilizers for example antioxidants, ultraviolet-ray absorbers, etc.
  • other active ingredients such as, for example, other herbicides, fungicides, insecticides, acaricides, fertilizers, etc.
  • herbicides which can be added to the compositions containing one or more compounds having general formula (I) are the following: acetochlor, acifluorfen, aclonifen, AKH-7088, alachlor, alloxydim, ametryn, amicarbazone, amidosulfuron, ami- trole, anilofos, asulam, atrazine, azafenidin, azimsulfu- ron, aziprotryne, BAY MKH 6561, beflubutamid, benazolin, benfluralin, benfuresate, bensulfuron, bensulide, benta- zone, benzfendizone, benzobicyclon, benzofenap, benzthia- Kunststoffon, bifenox, bilanafos, bispyribac-sodium, bromacil, bromobutide, bromofenoxim, bromoxynil, butachlor, buta-
  • the concentration of active substance in the above compositions can vary within a wide range, depending on the active compound, the applications for which they are destined, the environmental conditions and the type of formulation used. In general, the concentration of active substance preferably ranges from 1 to 90%.
  • the mixture is poured into water (30 ml) and extracted with ethyl ether (3 x 30 ml) ; the ether phase is washed with a saturated solution of sodium chloride, anhydrified with sodium sulfate, concentrated with a rotavapor.
  • the resi- due is purified by chromatography on a silica gel column eluating with hexane/ethyl acetate 7:3. 0.42 g of a solid with a .p. of 64°C are obtained; 1 H- and 19 F-NMR in accordance with the structure.
  • the herbicidal activity of the compounds of the invention in post-emergence was evaluated according to the following operating procedure.
  • the vegetable species of interest weeds or crops
  • vases having a diameter of over 10 cm, a height of 10 cm and containing sandy soil.
  • 10 vases were used for each vegetable species.
  • Water was added to each vase in a suitable quantity for a good germination of the seeds.
  • the vases were then divided into two groups, each group containing 5 vases for each weed or crop.
  • the first group of vases was treated with a hydro-acetone dispersion containing acetone at 10% v, the product to be evaluated at the desired concentration and Tween 20 at 0.5%.
  • the second group was only treated with a hydro- acetone solution containing acetone at 10% by volume and Tween 20 at 0.5%, and was used as a comparison (blank).
  • the herbicidal activity was evaluated on the basis of the following scale of values referring to the percentage of damage measured on the treated plants with respect to those not treated (blank) :
  • Table 1 indicates the results obtained treating the vegetable species listed below with compounds 1 and 2 at a dose of 50 g/ha:

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

Abstract

L'invention concerne des phénylpyrroles de formule générale (I) présentant une activité herbicide élevée.
PCT/EP2002/002297 2001-03-05 2002-03-01 Phenylpyrroles presentant une activite herbicide WO2002070476A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ITMI20010446 ITMI20010446A1 (it) 2001-03-05 2001-03-05 Fenilpirroli ad attivita' erbicida
ITMI2001A000446 2001-03-05

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WO2002070476A1 true WO2002070476A1 (fr) 2002-09-12

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012041789A1 (fr) 2010-10-01 2012-04-05 Basf Se Benzoxazinones herbicides

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0347488A1 (fr) * 1988-06-23 1989-12-27 American Cyanamid Company Arylpyrroles comme agents insecticides, acaricides et nématicides et procédé pour leur préparation
EP0351641A1 (fr) * 1988-07-18 1990-01-24 Nihon Bayer Agrochem K.K. 1-Phénylpyrrole
EP1061072A1 (fr) * 1999-06-17 2000-12-20 ISAGRO RICERCA S.r.l. Composés de pyrrole à haute activité herbicide et leur utilisation agronomique

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0347488A1 (fr) * 1988-06-23 1989-12-27 American Cyanamid Company Arylpyrroles comme agents insecticides, acaricides et nématicides et procédé pour leur préparation
EP0351641A1 (fr) * 1988-07-18 1990-01-24 Nihon Bayer Agrochem K.K. 1-Phénylpyrrole
EP1061072A1 (fr) * 1999-06-17 2000-12-20 ISAGRO RICERCA S.r.l. Composés de pyrrole à haute activité herbicide et leur utilisation agronomique

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012041789A1 (fr) 2010-10-01 2012-04-05 Basf Se Benzoxazinones herbicides

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