Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D521/00—Heterocyclic compounds containing unspecified 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
  • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
  • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
  • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
  • A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
  • C07D305/02—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings
  • C07D305/04—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
  • C07D305/08—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no 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 atoms
• • 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
  • C07D405/12—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 linked by a chain containing hetero atoms as chain links

Definitions

• the present invention relates to novel herbicidally active plant-growth-regulating sulfonylureas, to processes for their preparation, to compositions containing them as active ingredients, and to their use for controlling weeds, especially selectively in crops of useful plants, or for regulating and inhibiting the growth of plants.
• Urea compounds, triazine compounds and pyrimidine compounds which have herbicidal activity are generally known. Such compounds are described, for example, in EP-A-0007 687, 0030 138, 0073 562, 0 126711 and US-A-4618 363.
• the present invention therefore relates to compounds of the formula
• Q is a radical of the formula A or B
• R is hydrogen or methyl
• X is C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkylthio,
• Y is C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 haloalkylthio, C 1 -C 4 alkylthio,
• R a1 is hydrogen, halogen, -(Z) n -R 1 , nitro, -NR 2 R 3 , -C ⁇ C-R 4 , -O-CHR 5 -C ⁇ C-R 4 or
• R a2 is hydrogen, fluorine, chlorine or methyl
• R b is hydrogen, fluorine, chlorine, methyl or methoxy
• Z is O, S, SO or SO 2 ,
• n 0 or 1
• R 1 is C 1 -C 4 alkyl, C 1 -C 4 alkyl which is substituted by 1 to 4 halogen atoms, C 1 -C 3 alkoxy or
• C 1 -C 3 alkylthio or is C 2 -C 4 alkenyl, or C 2 -C 4 alkenyl which is substituted by 1 to 4 halogen atoms,
• R 2 is hydrogen or C 1 -C 3 alkyl
• R 3 is hydrogen, C 1 -C 3 alkyl or C 1 -C 3 alkoxy
• R 4 is hydrogen or C 1 -C 4 alkyl
• R 5 is hydrogen or methyl
• R 6 is C 1 -C 6 alkyl or C 3 -C 6 cycloalkyl
• R a1 and R a2 are preferably hydrogen. If Q is such a radical of the formula A, then R is preferably hydrogen, X is preferably methyl, methoxy, chlorine, -OCHF 2 or -OCH 2 CF 3 and Y is preferably methyl, methoxy, chlorine, -OCHF 2 or -N(CH 3 ) 2 .
• Q is a radical of the formula B in which R b is hydrogen.
• R is preferably hydrogen
• X is preferably methyl, methoxy, ethoxy, -OCHF 2 or -OCH 2 CF 3
• Y is preferably methyl, methoxy, chlorine, -N(CH 3 ) 2 or cyclopropyl.
• X and Y independently of one another are methyl or methoxy.
• R is hydrogen
• Another group of preferred compounds of the formula I contain, as substituent Q, a radical of the formula
• R b is as defined above.
• Preferred compounds amongst these are those in which R b is hydrogen.
• halogen is to be understood as meaning fluorine, chlorine, bromine and iodine, preferably fluorine, chlorine and bromine.
• alkyl groups in the definitions of the substituents can be straight-chain or branched and are, for example, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl or tert-butyl.
• the alkyl groups as, or in the, substituents preferably have 1-3 carbon atoms.
• Alkenyl is to be understood as meaning straight-chain or branched alkenyl, for example vinyl, allyl, methallyl, 1-methylvinyl or but-2-en-1-yl.
• Preferred alkenyl radicals are those having a chain length of 2 to 4 carbon atoms.
• Haloalkyl is, for example, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 2-fIuoroethyl, 2-chlonoethyl, 2,2,2-trichloroethyl and 3,3,3-trifluoropropyl; preferably trichloromethyl,
• Alkoxy is, for example, methoxy, ethoxy, propyloxy, i-propyloxy, n-butyloxy, iso-butyloxy, sec-butyioxy and tert-butyloxy; preferably methoxy and ethoxy.
• Haloalkoxy is, for example, difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2-fluoroethoxy, 2-chloroethoxy and 2,2-difluoroethoxy;
• Alkyl thio is, for example, methylthio, ethyl thio, propylthio, isopropylthio, n-butylthio, iso-butylthio, sec-butylthio or tert-butylthio, preferably methylthio and ethylthio.
• alkoxyalkoxy examples are: methoxymethoxy, methoxyethoxy, methoxypropyloxy, ethoxymethoxy, ethoxyethoxy and propyloxymethoxy.
• Alkylamino is, for example, methylamino, ethylamino, n-propylamino or
• Dialkylamino is, for example, dimethylamino, methylethylamino, diethylamino or n-propylmethylamino.
• the invention also embraces the salts which the compounds of the formula I can form with amines, alkali metal bases or alkaline earth metal bases or quaternary ammonium bases.
• Preferred alkali metal hydroxides and alkaline earth metal hydroxides as salt-forming substances are lithium hydroxide, sodium hydroxide, potassium hydroxide, magnesium hydroxide or calcium hydroxide, but in particular sodium hydroxide or potassium hydroxide.
• amines which are suitable for salt formation are primary, secondary and tertiary aliphatic and aromatic amines such as methylamine, ethylamine, n-propylamine, iso-propylamine, the four isomeric butylamine radicals, n-amylamine, iso-amylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, pentadecylamine, hexadecylamine, heptadecylamine, octadecylamine, methylethylamine,
• primary, secondary and tertiary aliphatic and aromatic amines such as methylamine, ethylamine, n-propylamine, iso-propylamine, the four isomeric butylamine radicals, n-amylamine, iso-amylamine, hexylamine, hepty
• methylisopropylamine methylhexylamine, methylnonylamine, methylpentadecylamine, methyloctadecylamine, ethylbutylamine, ethylheptylamine, ethyloctylamine,
• hexylheptylamine hexyloctylamine, dimethylamine, diethylamine, di-n-propylamine, di-iso-propylamine, di-n-butylamine, di-n-amylamine, di-iso-amylamine, dihexylamine, diheptylamine, dioctylamine, ethanolamine, n-propanolamine, iso-propanolamine, N,N-diethylethanolamine, N-ethylpropanolamine, N-butylethanolamine, allylamine, n-butenyl-2-amine, n-pentenyl-2-amine, 2,3-dimethylbutenyl-2-amine,
• heterocyclic amines for example pyridine, quinoline, ⁇ so-quinoline, morpholine, piperidine, pyrrolidine, indoline, quinuclidine and azepine; primary arylamines, for example anilines, methoxyanilines,
• o,m,p-chloroanilines but in particular ethyl-, propyl-, diethyl- or triethylamine, but
• examples of quaternary ammonium bases are the cations of haloammonium
• salts for example the tetramethylammonium cation, the trimethylbenzylammonium
• the compounds of the formula I according to the invention can be prepared for example by reacting suitable sulfonamides with corresponding pyrimidine or triazine derivatives.
• reaction which give compounds of the formula I are advantageously carried out in aprotic, inert organic solvents.
• solvents are hydrocarbons such as benzene, toluene, xylene or cyclohexane, chlorinated hydrocarbons such as dichloromethane,
• reaction temperatures are preferably between -20° and +120°C.
• the reactions are slightly exothermic and can be carried out at room temperature.
• the reaction times can also be shortened by adding a few drops of base as reaction catalyst.
• Suitable bases are, in particular, tertiary amines such as trimethylamine, triethylamine, quinuclidine,
• inorganic bases such as hydrides, such as sodium hydride or calcium hydride, hydroxides such as sodium hydroxide and potassium hydroxide, carbonates such as sodium carbonate and potassium carbonate or hydrogen carbonates such as potassium hydrogen carbonate and sodium hydrogen carbonate, can also be used as bases.
• the end products of the formula I can be isolated by concentration and/or evaporation of the solvent and purified by recrystallisation or trituration of the solid residue in solvents in which they are not freely soluble, such as ethers, aromatic hydrocarbons or chlorinated hydrocarbons.
• EP-A-336587 describes a further preparation method: d) reaction of the compound of the formula
• R a1 , R a2 and R b are as defined above.
• R d is methyl, phenyl or substituted phenyl
• R x is bromine or iodine
• T 2 is hydrogen, C 1 -C 5 alkyl or halogen
• T 3 is hydrogen or C 1 -C 5 alkyl which is optionally substituted by halogen
• R y is i-propyl or benzyl
• HAL is halogen.
• A-B is a compound of the formula
• HT 1 C CT 2 T 3 or HC ⁇ CR 4 or a combination of CO and R 6 OH, in which T 1 , T 2 , T 3 , R 4 and R 6 have the abovementioned meanings.
• the active ingredients of the formula I are applied successfully at application rates of 0.001 to 2 kg/ha, in particular 0.005 to 1 kg/ha.
• the dosage rate required for the desired action can be determined by experiments. It depends on the type of action, the development stage of the crop plant and of the weed and on the application (location, time, method) and, due to these parameters, can vary within wide ranges.
• the compounds of the formula I are distinguished by growth-inhibiting and herbicidal properties which make them outstandingly suitable for use in crops of useful plants, in particular in cereals, cotton, soya beans, oilseed rape, maize and rice, their use in soya bean crops and cereals being especially preferred. Weeds in soya bean crops are preferably controlled postemergence.
• the compounds of the formula I are particularly distinguished by their good degradability.
• the invention also relates to herbicidal and plant-growth-regulating compositions which comprise a novel active ingredient of the formula I, and to methods for inhibiting the growth of plants.
• Plant growth regulators are substances which cause agronomically desirable biochemical and/or physiological and/or morphological modifications in/on the plant.
• the active ingredients comprised in the compositions according to the invention affect plant growth in many ways, depending on the point in time of application, the dosage rate, the type of application and the prevailing environment.
• plant growth regulators of the formula I can inhibit the vegetative growth of plants. This type of action is of interest on lawns, in the production of ornamentals, in fruit plantations, on verges, on sports grounds and industrial terrain, but also in the targeted inhibition of secondary shoots, such as in tobacco.
• inhibition of the vegetative growth in cereals by strengthening the stems results in reduced lodging, and similar agronomic effects are achieved in oilseed rape, sunflowers, maize and other crop plants. Furthermore, inhibition of the vegetative growth means that the number of plants per area can be increased.
• Another field in which growth inhibitors can be applied is the selective control of ground-cover plants in plantations or crops with plenty of space between the rows, by powerful growth inhibition without destroying these cover crops, so that competition with the main crop is eliminated, but the agronomically positive effects such as prevention of erosion, nitrogen fixation and loosening of the soil, are retained.
• a method for inhibiting plant growth is understood as meaning controlling the natural development of the plant without altering the life cycle of the plant, which is determined by its genetic make-up, in the sense of a mutation.
• the method of growth regulation is applied at a particular point in time of the development of the plant, which is to be determined in the particular case.
• the active ingredients of the formula I can be applied before or after emergence of the plants, for example already to the seeds or seedlings, to roots, tubers, stalks, leaves, flowers or other parts of the plant. This can be effected, for example, by applying the active ingredient, as pure active ingredient or in the form of a composition, to the plants and/or by treating the nutrient substrate of the plant (soil).
• the dissolved active ingredient is applied to mineral granule carriers or polymerised granules (urea/formaldehyde) and allowed to dry. If desired, a coating can be applied
• the compounds of the formula I are employed in unaltered form, as obtained from synthesis, or, preferably, together with the auxiliaries conventionally used in the art of formulation, and they are therefore processed in a known manner to give, for example, emulsifiable concentrates, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granules and also encapsulations, for example in polymeric substances.
• the application methods such as spraying, atomising, dusting, wetting, scattering or pouring, as well as the type of the compositions are selected to suit the intended aims and the prevailing circumstances.
• compositions, preparations or combinations comprising the active ingredient of the formula I and, if desired, one or more solid or liquid additives, are prepared in a known manner, for example by intimately mixing and/or grinding the active ingredients with extenders, for example solvents, solid carriers and, if desired, surface-active compounds (surfactants).
• extenders for example solvents, solid carriers and, if desired, surface-active compounds (surfactants).
• aromatic hydrocarbons in particular the fractions C 8 to C 12 , such as mixtures of alkylbenzenes, for example xylene mixtures or alkylated naphthalenes; aliphatic and cycloahphatic hydrocarbons such as paraffins, cyclohexane or tetrahydronaphthalene; alcohols such as ethanol, propanol or butanol; glycols as well as their ethers and esters, such as propylene glycol or dipropylene glycol ether, ketones such as cyclohexanone, isophorone or diacetone alcohol, strongly polar solvents such as N-methyl-2-pyrrolidone, dimethyl sulfoxide or water; vegetable oils and esters thereof, such as rapeseed oil, castor oil or soya oil; silicone oils may also be suitable.
• aromatic hydrocarbons in particular the fractions C 8 to C 12 , such as mixtures of alkylbenzenes, for example
• Solid carriers which are used, for example for dusts and dispersible powders are, as a rule, natural ground minerals such as calcite, talc, kaolin, montmorillonite or attapulgite.
• highly-disperse silica or highly-disperse absorptive polymers Possible paniculate, adsorptive carriers for granules are either porous types, for example pumice, brick grit, sepiolite or bentonite, or non-sorptive carrier materials, such as calcite or sand.
• a large number of pregranulated materials of inorganic or organic nature can be used such as, in particular, dolomite or comminuted plant residues.
• Suitable surface-active compounds are non-ionic, cationic and/or anionic surfactants having good emulsifying, dispersing and wetting properties, depending on the nature of the active ingredient of the formula I to be formulated.
• Surfactants are also to be understood as meaning mixtures of surfactants.
• Anionic surfactants which are suitable can be either so-called water-soluble soaps or water-soluble synthetic surface-active compounds.
• Suitable soaps which may be mentioned are the alkali metal salts, alkaline earth metal salts or substituted or unsubstituted ammonium salts of higher fatty acids (C 10 -C 22 ), such as, for example, the sodium salts or potassium salts of oleic or stearic acid, or of natural mixtures of fatty acids which can be obtained, for example, from coconut oil or tallow oil. Mention must also be made of the fatty acid methyltaurinates.
• fatty alcohol sulfonates are, as a rule, in the form of alkali metal salts, alkaline earth metal salts or unsubstituted or substituted ammonium salts, and have an alkyl radical having 8 to 22 carbon atoms, alkyl also including the alkyl moiety of acyl radicals, for example the sodium salt or calcium salt of ligninsulfonic acid, of the dodecylsulfiiric ester or of a fatty alcohol sulfate mixture prepared from natural fatty acids.
• This group also includes the salts of the sulfuric esters and sulfonic acids of fatty alcohol/ethylene oxide adducts.
• the sulfonated benzimidazole derivatives preferably contain 2 sulfonyl groups and one fatty acid radical having 8-22 carbon atoms.
• alkylarylsulfonates are the sodium, calcium or triethanolamine salts of
• dodecylbenzenesulfonic acid of dibutylnaphthalenesulfonic acid, or of a
• Suitable compounds are the corresponding phosphates, such as the salts of the phosphoric ester of p-nonylphenol/(4-14)-ethylene oxide adduct, orphospholipids.
• Suitable non-ionic surfactants are mainly polyglycol ether derivatives of aliphatic or cycloaliphatic alcohols, saturated or unsaturated fatty acids and alkylphenols which can contain 3 to 30 glycol ether groups and 8 to 20 carbon atoms in the (aliphatic)
• hydrocarbon radical and 6 to 18 carbon atoms in the alkyl radical of the alkylphenols are hydrocarbon radical and 6 to 18 carbon atoms in the alkyl radical of the alkylphenols.
• non-ionic surfactants which are suitable are the water-soluble polyethylene oxide adducts with polypropylene glycol, ethylenediaminopolypropylene glycol and
• alkylpolypropylene glycol which have 1 to 10 carbon atoms in the alkyl chain and which contain 20 to 250 ethylene glycol ether groups and 10 to 100 propylene glycol ether groups.
• the abovementioned compounds customarily contain 1 to 5 ethylene glycol units per propylene glycol unit.
• non-ionic surfactants examples include butyl-ionic surfactants
• nonylphenolpolyethoxyethanols castor oil polyglycol ethers, polypropylene/polyethylene oxide adducts, tributylphenoxypolyethoxyethanol, polyethylene glycol and
• Suitable substances are fatty acid esters of polyoxyethylenesorbitan, such as polyoxyethylenesorbitan trioleate.
• the canonic surfactants are mainly quaternary ammonium salts which contain at least one alkyl radical having 8 to 22 carbon atoms as N substituents and which have lower halogenated or free alkyl, benzyl or lower hydroxyalkyl radicals as further substituents.
• the salts are preferably in the form of halides, methylsulfates or ethylsulfates, for example stearyltrimethylammonium chloride or benzyldi(2-chloroethyl)ethylammonium bromide.
• the preparations comprise 0.1 to 99 %, in particular 0.1 to 95 %, of active ingredient of the formula 1, 1 to 99 % of the solid or liquid additive and 0 to 25 %, in particular 0.1 to 25 %, of a surfactant.
• compositions are more preferred as commercial goods, the end user, as a rule, uses dilute compositions.
• compositions can also comprise further additions such as stabilisers, for example epoxidised or unepoxidised vegetable oils (epoxidised coconut oil, rapeseed oil or soya oil), defoamers, for example silicone oil, preservatives, viscosity regulators, binders, tackifiers as well as fertilisers or other active ingredients for achieving specific effects.
• stabilisers for example epoxidised or unepoxidised vegetable oils (epoxidised coconut oil, rapeseed oil or soya oil), defoamers, for example silicone oil, preservatives, viscosity regulators, binders, tackifiers as well as fertilisers or other active ingredients for achieving specific effects.
• Emulsifiable concentrates are:
• Active ingredient 1 to 20 %, preferably 5 to 10 %
• Surface-active agent 5 to 30 %, preferably 10 to 20 %
• Liquid carrier 15 to 94 %, preferably 70 to 85 % Dusts:
• Active ingredient 0.1 to 10 %, preferably 0.1 to 1 %
• Solid carrier 99.9 to 90 %, preferably 99.9 to 99 %
• Active ingredient 5 to 75 %, preferably 10 to 50 %
• Surface-active agent 1 to 40 %, preferably 2 to 30 %
• Active ingredient 0.5 to 90 %, preferably 1 to 80 %
• Surface-active agent 0.5 to 20 %, preferably 1 to 15 %
• Solid carrier 5 to 95 %, preferably 15 to 90 %
• Active ingredient 0.5 to 30 %, preferably 3 to 15 %
• Solid carrier 99.5 to 70 %, preferably 97 to 85 %
• dimethylformamide is stirred for 24 hours at 100 to 105°C.
• 14.3 g of the title compound with a melting point of 180 to 182°C are obtained by pouring the mixture into water, neutralising it with hydrochloric acid (10 %) and extracting it with ethyl acetate and drying and concentrating the extract until it crystallises.
• the suspension is treated with 15 ml of trifluoroacetic acid with cooling, stirred for 10 minutes at 10 to 15 °C and filtered, and the filtrate is concentrated.
• the residue is purified by chromatography over silica gel using ethyl acetate/methanol (5:1), and 11.2 g of the title compound with a melting point of 178 to 181°C are obtained.
• the active ingredient is mixed thoroughly with the additives and the mixture is ground thoroughly in a suitable mill. This gives wettable powders which can be diluted with water to give suspensions of any desired concentration.
• Emulsions of any desired concentration can be prepared from such concentrates by dilution with water.
• Talc 99.9 % - Kaolin - 99 % Ready-for-use dusts are obtained by intimately mixing the carriers with the active ingredient.
• the active ingredient is mixed with the additives, and the mixture is ground and moistened with water. This mixture is extruded and subsequently dried in a stream of air.
• the kaolin which has been moistened with polyethylene glycol is coated uniformly with the finely-ground active ingredient. Dust-free coated granules are obtained in this manner.
• Example B1 Herbicidal action before emergence of the plants
• Plastic pots are filled with expanded vermiculite (density: 0.135 g/cm 3 , water adsorption capacity: 0.5651/1).
• the non-adsorptive vermiculite is saturated with an aqueous active ingredient emulsion in deionised water which comprises the active ingredients at a concentration of 70 ppm, and seeds of the following plants arc then sown onto the surface: Nasturtium officinalis, Agrostis tenuis, Stellaria media and Digitaria sanguinalis.
• the test containers are then kept in a controlled-environment cabinet at a temperature of 20°C, an illumination of approx. 20 kLux and a relative atmospheric humidity of 70 %.
• the pots are covered with translucent material to increase the local atmospheric humidity and watered with deionised water. After day 5, 0.5 % of a commercially available liquid fertiliser is added to the irrigation water. 12 days after sowing, the test is evaluated and the effect on the test plants is assessed using the following key:
• a number of monocotyledon and dicotyledon weeds were sprayed after emergence (in the 4- to 6-leaf stage) with an aqueous dispersion of active ingredient according to Example F6 at a dosage rate of 8-500 g of active ingredient per hectare, and the plants were kept at 24°-26°C and a relative atmospheric humidity of 45-60 %. The test is evaluated 15 days after the treatment.

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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)

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• 1993
  • 1993-02-09 AU AU34541/93A patent/AU3454193A/en not_active Abandoned
  • 1993-02-09 WO PCT/EP1993/000315 patent/WO1993017015A1/en active Application Filing
  • 1993-02-19 IL IL104798A patent/IL104798A0/xx unknown
  • 1993-02-19 LT LTIP347A patent/LT3020B/lt not_active IP Right Cessation
  • 1993-02-19 ZA ZA931177A patent/ZA931177B/xx unknown
  • 1993-02-19 LV LVP-93-131A patent/LV10247B/xx unknown
  • 1993-02-19 MX MX9300893A patent/MX9300893A/es unknown

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