WO2000042032A1 - 2-imino-thiazolines substituees - Google Patents

2-imino-thiazolines substituees Download PDF

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Publication number
WO2000042032A1
WO2000042032A1 PCT/EP2000/000045 EP0000045W WO0042032A1 WO 2000042032 A1 WO2000042032 A1 WO 2000042032A1 EP 0000045 W EP0000045 W EP 0000045W WO 0042032 A1 WO0042032 A1 WO 0042032A1
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WO
WIPO (PCT)
Prior art keywords
chlorine
methyl
fluorine
substituted
cyano
Prior art date
Application number
PCT/EP2000/000045
Other languages
German (de)
English (en)
Inventor
Klaus-Helmut Müller
Mark Wilhelm Drewes
Dieter Feucht
Rolf Pontzen
Ingo Wetcholowsky
Original Assignee
Bayer Aktiengesellschaft
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer Aktiengesellschaft filed Critical Bayer Aktiengesellschaft
Priority to AU24353/00A priority Critical patent/AU2435300A/en
Publication of WO2000042032A1 publication Critical patent/WO2000042032A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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
    • C07D277/38—Nitrogen atoms
    • C07D277/44—Acylated amino or imino radicals
    • C07D277/48—Acylated amino or imino radicals by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof, e.g. carbonylguanidines

Definitions

  • the invention relates to new substituted 2-imino-thiazolines, processes for their preparation and their use as herbicides.
  • Q oxygen or sulfur
  • R ! for optionally substituted by cyano, halogen or C, -C-alkoxy alkyl with 1 to 6 carbon atoms, for each optionally substituted by cyano or halogen alkenyl or alkynyl each having 2 to 6 carbon atoms, for each optionally substituted by cyano, halogen or - - alkyl
  • R 2 represents hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or alkyl or alkoxycarbonyl, each optionally substituted by cyano, halogen or C, -C 4 -alkoxy, each having up to 6 carbon atoms,
  • R 3 represents hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or represents alkyl or alkoxycarbonyl, each optionally substituted by cyano, halogen or C, -C 4 -alkoxy, each having up to 6 carbon atoms, and
  • Arylalkyl each having 6 or 10 carbon atoms in the aryl groups and optionally 1 to 4 carbon atoms in the alkyl part, or for each optionally by nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, C r C 4 alkyl, C, -C 4 haloalkyl , C, -C 4 -alkoxy, C, -C 4 -haloalkoxy, C, -C 4 -alkylthio, C, -C 4 -haloalkylthio, C, -C 4 -alkylsulfinyl, C, -C 4 -
  • hydrocarbon chains such as alkyl
  • the hydrocarbon chains are also straight-chain or branched, in each case in conjunction with heteroatoms, such as in alkoxy.
  • R 1 preferably represents in each case optionally by cyano, fluorine, chlorine,
  • preferably hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or in each case optionally by fluorine or chlorine substituted methyl, ethyl, n- or i-propyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl.
  • R 1 preferably represents hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or in each case optionally by cyano,
  • R 4 preferably represents in each case optionally by cyano, fluorine, chlorine, bromine,
  • Isoxazolyl isoxazolylmethyl, thiazolyl, thiazolylmethyl, oxadiazolyl, oxadiazoylmethyl, thiadiazolyl, thiadiazolylmethyl, pyridinyl, quinolinyl, isoquinolinyl, pyridinylmethyl, pyrimidinyl, pyrimidinylmethyl.
  • Trifluoromethylsulfonyl dimethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, dimethylaminocarbonyl or od; Dimethylaminosulfonyl substituted phenyl or benzyl, or for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy , Methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, trifluoromethylsulfmyl,
  • R 2 particularly preferably represents chlorine or bromine, or methyl, ethyl, n- or i-propyl which may be substituted by fluorine or chlorine.
  • R 3 particularly preferably represents hydrogen, cyano, fluorine, chlorine, bromine or methyl which is optionally substituted by fluorine or chlorine.
  • R 4 particularly preferably represents in each case optionally by fluorine, chlorine or
  • R 1 very particularly preferably represents methyl, ethyl, n- or i-propyl, which is optionally substituted by fluorine or chlorine
  • n-, i- or s-butyl represents propenyl, butenyl, propynyl or butynyl which is optionally substituted by fluorine or chlorine, for each cyclopropyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclopentylmethyl or cyclohexylmethyl optionally substituted by fluorine, chlorine or methyl, for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-
  • R 2 very particularly preferably represents chlorine or bromine, or methyl or ethyl which is in each case optionally substituted by fluorine or chlorine.
  • R 3 very particularly preferably represents hydrogen, chlorine, bromine or methyl which is optionally substituted by fluorine or chlorine.
  • R 4 very particularly preferably represents in each case optionally by nitro
  • R 4 most preferably represents phenyl which contains a substituent from the series fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, difluoromethoxy, trifluoromethoxy in the 3- or meta position and, if appropriate, a further substituent from the series Contains fluorine, chlorine, trifluoromethyl, the grouping 3-trifluoromethylphenyl being particularly emphasized for R 4 .
  • radicals listed above or those specified in preferred ranges apply both to the end products of the formula (I) and correspondingly to the starting or intermediate products required in each case for the preparation. These radical definitions can be combined with one another, that is to say also between the specified preferred ranges. According to the invention, preference is given to the compounds of the formula (I) in which there is a combination of the meanings listed above as preferred (preferred).
  • the new substituted 2-imino-thiazolines of the general formula (I) have interesting biological properties. They are particularly characterized by strong herbicidal - and to a certain extent also by insecticidal - effectiveness.
  • R 2 , R 3 and R 4 have the meaning given above,
  • R 1 has the meaning given above and
  • Y represents halogen or alkylsulfonyl
  • reaction sequence in process (a) according to the invention can be outlined by the following formula:
  • Formula (II) provides a general definition of the 2-iminothiazolines to be used as starting materials in processes (a) and (b) according to the invention for the preparation of compounds of the general formula (I).
  • R 2 , R 3 and R 4 preferably have those meanings which are already preferred, particularly preferred, very particularly preferred or most preferred in connection with the description of the compounds of the general formula (I) according to the invention for R 2 , R 3 and R 4 have been specified.
  • the starting materials of the general formula (II) are known and / or can be prepared by processes known per se (cf. US-A-5459277, EP-A-545431).
  • Formula (III) provides a general definition of the halogeno- (di) thioformic acid esters to be used further as starting materials in process (a) according to the invention.
  • Q and R 1 have the meaning which have already been given above in connection with the description of the compounds of the general formula (I) according to the invention as preferred, particularly preferred or very particularly preferred for Q and R ';
  • X preferably represents fluorine, chlorine or bromine.
  • the starting materials of the general formula (III) are known synthetic chemicals.
  • Formula (V) provides a general definition of the compounds to be used as starting materials in process (b) according to the invention for the preparation of compounds of the general formula (I).
  • R 1 preferably has the meaning which has already been given above in connection with the description of the compounds of the general formula (I) according to the invention as preferred, particularly preferred or very particularly preferred for R 1 ;
  • Y preferably represents fluorine, chlorine, bromine, methylsulfonyl or ethylsulfonyl, in particular chlorine.
  • the starting materials of the general formula (V) are known organic synthetic chemicals.
  • Process (a) according to the invention for the preparation of compounds of the general formula (I) is optionally carried out using a reaction auxiliary.
  • a reaction auxiliary The usual inorganic or organic bases or are generally used as reaction aids for the process according to the invention
  • Acid acceptors into consideration preferably include alkali metal or earth alkali metal acetates, amides, carbonates, hydrogen carbonates, hydrides, hydroxides or alkanolates, such as sodium, potassium or calcium acetate, lithium, sodium, potassium or calcium amide, sodium , Potassium or calcium carbonate, sodium, potassium or calcium hydrogen carbonate, lithium, sodium, potassium or calcium hydride, lithium, sodium, potassium or calcium hydroxide,
  • DABCO 1,4-diazabicyclo [2,2,2] octane
  • DBN 1,5-diazabicyclo [4,3,0] non-5-ene
  • DBU 1,8-diazabicyclo [5,4,0] -undec-7-ene
  • Phase transfer catalysts are also suitable as further reaction aids for process (a) according to the invention.
  • Examples of such catalysts are:
  • Tetrabutylammonium bromide Tetrabutylammonium bromide, tetrabutylammonium chloride, tetraoctylammonium chloride, tetrabutylammonium hydrogen sulfate, methyl trioctylammonium chloride, hexadecyl trimethylammonium chloride, hexadecyl trimethylammonium bromide, benzylchloride, benzylchloride, benzyl methylammonium hydroxide, benzyl triethylammonium hydroxide, benzyl tributyl ammonium chloride, benzyl tributylammonium bromide, tetrabutylphosphonium bromide, tetrabutylphosphonium chloride, tributyl hexadecylphosphonium bromide, butyl triphenyl Tetraphenylphosphonium bromid
  • Process (b) according to the invention for the preparation of compounds of the general formula (I) is carried out in the presence of a metal compound.
  • a metal compound come here preferably alkali metal or alkaline earth metal acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkanolates, such as sodium, potassium or calcium acetate, lithium, sodium, potassium or Calcium amide, sodium, potassium or calcium carbonate, sodium, potassium or calcium hydrogen carbonate, lithium, sodium, potassium or calcium hydride,
  • Processes (a) and (b) according to the invention for the preparation of the compounds of the general formula (I) are preferably carried out using diluents.
  • suitable diluents for carrying out the processes according to the invention are, above all, inert organic solvents. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene,
  • reaction temperatures can be varied within a substantial range when carrying out processes (a) and (b) according to the invention. In general, temperatures between 0 ° C and 150 ° C, preferably between
  • Processes (a) and (b) according to the invention are generally carried out under normal pressure. However, it is also possible to carry out the processes according to the invention under elevated or reduced pressure - generally between 0.1 bar and 10 bar.
  • the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a larger excess.
  • the reaction is generally carried out in a suitable diluent and the reaction mixture is generally stirred at the required temperature for several hours. Working up is carried out according to customary methods (cf. the production examples).
  • the active compounds according to the invention can be used as defoliants, desiccants, haulm killers and in particular as weed killers. Weeds in the broadest sense are all plants that grow in places where they are undesirable. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.
  • plants and parts of plants can be treated.
  • Plants are understood here to mean all plants and plant populations, such as desired and unwanted wild plants or crop plants (including naturally occurring crop plants).
  • Cultivated plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which can or cannot be protected by plant breeders' rights.
  • Plant parts are to be understood to mean all above-ground and underground parts and organs of plants, such as shoots, leaves, flowers and roots, examples being leaves, needles, stems, stems, flowers, fruiting bodies, Fruits and seeds as well as roots, tubers and rhizomes are listed.
  • the plant parts also include crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
  • the treatment of the plants and parts of plants with the active compounds according to the invention is carried out directly or by acting on their surroundings.
  • Habitat or storage space according to the usual treatment methods, e.g. by dipping, spraying, vaporizing, atomizing, scattering, brushing and, in the case of propagation material, in particular seeds, furthermore by single- or multi-layer coating.
  • the active compounds according to the invention can e.g. can be used in the following plants:
  • Galinsoga Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Dutilon, Emo Viola, galeopsis, papaver, centaurea, trifolium, ranunculus, taraxacum.
  • the active compounds according to the invention are suitable for combating total weeds, e.g. on industrial and track systems and on paths and squares with and without tree cover.
  • the active compounds according to the invention for weed control in permanent crops e.g. Forest, ornamental wood, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants, on ornamental and sports turf and pasture land as well as for selective purposes Weed control can be used in annual crops.
  • the compounds of formula (I) according to the invention show strong herbicidal activity and a broad spectrum of activity when used on the soil and on above-ground parts of plants. To a certain extent, they are also suitable for the selective control of monocotyledon and dicotyledon weeds in monocotyledon and dicotyledon crops, both in the pre-emergence and in the post-emergence process.
  • the active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active substance-impregnated natural and synthetic substances and very fine encapsulations in polymeric substances.
  • formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is liquid solvents and / or solid
  • Carriers optionally using surface-active agents, thus emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can also be used as auxiliary solvents.
  • auxiliary solvents e.g. organic solvents
  • aromatics such as xylene, toluene, or alkylnaphthalenes
  • chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride
  • aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol as well as their ethers and esters, ketones such as
  • Possible solid carriers are: e.g. Ammonium salts and natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite as well as synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust,
  • natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth
  • synthetic rock powders such as highly disperse silica, aluminum oxide and silicates are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, se
  • coconut shells, corn cobs and tobacco stems as emulsifying and / or foaming agents are possible: e.g. non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersants are: e.g. Lignin sulfite leaching and methyl cellulose.
  • non-ionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates
  • Possible dispersants are: e.g. Lignin sulfit
  • adhesives such as carboxymethylcellulose, natural and synthetic powdered, granular or latexfb '-shaped polymers are used, such as gum arabic, polyvinyl alcohol, polyvinyl acetate and natural phospholipids lipids such as cephalins and lecithins and synthetic phospholipids.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • the active compounds according to the invention can also be used for combating weeds, in a mixture with known herbicides, finished formulations or tank mixes being possible.
  • herbicides are suitable for the mixtures, for example acetochlor, acifluorfen (sodium), aclonifen, alachlor, alloxydim (sodium), ametryne, amidochlor, amidosulfuron, anilofos, asulam, atrazine, azafenidin, azimsulfuron, benazolin (-ethyl), benfuresate , Bensulfuron (-methyl), bentazone, benzofenap, benzoylprop (-ethyl), bialaphos, bifenox, bispyribac (-sodium),
  • the active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the usual way, e.g. by pouring, spraying, spraying, sprinkling.
  • the active compounds according to the invention can be applied both before and after emergence of the plants. They can also be worked into the soil before sowing.
  • the amount of active ingredient used can vary over a wide range. It essentially depends on the type of effect desired. In general, the application rates are between 1 g and 10 kg of active ingredient per hectare of soil, preferably between 5 g and 5 kg per ha.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
  • Seeds of the test plants are sown in normal soil. After about 24 hours, the soil is sprayed with the active ingredient preparation in such a way that the desired amount of active ingredient is applied per unit area.
  • the concentration of the spray liquor is chosen so that the desired amount of active compound is applied in 1000 liters of water per hectare.
  • the degree of damage to the plants is rated in% damage compared to the development of the untreated control.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
  • Test plants which have a height of 5 to 15 cm are sprayed with the active compound preparation in such a way that the desired amounts of active compound are applied per unit area.
  • the concentration of the spray liquor is chosen so that the desired amounts of active compound are applied in 1000 l of water / ha.
  • the degree of damage to the plants is rated in% damage compared to the development of the untreated control.
  • the compounds according to Preparation Examples 1, 2, 3, 4 and 5 show with largely good tolerance to crop plants, such as e.g. Wheat, effective against weeds.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

L'invention concerne de nouvelles 2-imino-thiazolines substituées de la formule générale (I) dans laquelle Q, R<1>, R<2>, R<3> et R<4> ont les significations mentionnées dans la description. L'invention concerne en outre des procédés permettant de les préparer et leur utilisation comme herbicides.
PCT/EP2000/000045 1999-01-12 2000-01-05 2-imino-thiazolines substituees WO2000042032A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU24353/00A AU2435300A (en) 1999-01-12 2000-01-05 Substituted 2-imino thiazolines

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE1999100824 DE19900824A1 (de) 1999-01-12 1999-01-12 Substituierte 2-Imino-thiazoline
DE19900824.8 1999-01-12

Publications (1)

Publication Number Publication Date
WO2000042032A1 true WO2000042032A1 (fr) 2000-07-20

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Application Number Title Priority Date Filing Date
PCT/EP2000/000045 WO2000042032A1 (fr) 1999-01-12 2000-01-05 2-imino-thiazolines substituees

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AU (1) AU2435300A (fr)
DE (1) DE19900824A1 (fr)
WO (1) WO2000042032A1 (fr)

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2204145A1 (de) * 1971-01-29 1972-11-23 Parke, Davis & Co., Detroit, Mich. (V.StA.) 2- eckige Klammer auf eckige Klammer auf eckige Klammer auf(4-Thiazolin-2yliden) amino eckige Klammer zu (thio) methylen eckige Klammer zu amino eckige Klammer zu thiazoliumsalze
EP0446802A1 (fr) * 1990-03-12 1991-09-18 Sumitomo Chemical Company, Limited Iminothiazolines, leur production, leur utilisation comme herbicide et les intermédiaires nécessaires à leur production
JPH0539276A (ja) * 1991-08-05 1993-02-19 Sumitomo Chem Co Ltd イミノチアゾリン誘導体の製造法
EP0529481A1 (fr) * 1991-08-28 1993-03-03 Sumitomo Chemical Company, Limited Iminothiazolines, leur préparation et utilisation comme herbicides
EP0529482A1 (fr) * 1991-08-23 1993-03-03 Sumitomo Chemical Company, Limited Iminothiazolines, leur préparation et utilisation comme herbicides et intermédiaires necessaires à leur production
EP0531970A1 (fr) * 1991-09-11 1993-03-17 Sumitomo Chemical Company, Limited Composition herbicide
WO1998042703A1 (fr) * 1997-03-24 1998-10-01 Basf Aktiengesellschaft Derives de thiazolimine

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2204145A1 (de) * 1971-01-29 1972-11-23 Parke, Davis & Co., Detroit, Mich. (V.StA.) 2- eckige Klammer auf eckige Klammer auf eckige Klammer auf(4-Thiazolin-2yliden) amino eckige Klammer zu (thio) methylen eckige Klammer zu amino eckige Klammer zu thiazoliumsalze
EP0446802A1 (fr) * 1990-03-12 1991-09-18 Sumitomo Chemical Company, Limited Iminothiazolines, leur production, leur utilisation comme herbicide et les intermédiaires nécessaires à leur production
JPH0539276A (ja) * 1991-08-05 1993-02-19 Sumitomo Chem Co Ltd イミノチアゾリン誘導体の製造法
EP0529482A1 (fr) * 1991-08-23 1993-03-03 Sumitomo Chemical Company, Limited Iminothiazolines, leur préparation et utilisation comme herbicides et intermédiaires necessaires à leur production
EP0529481A1 (fr) * 1991-08-28 1993-03-03 Sumitomo Chemical Company, Limited Iminothiazolines, leur préparation et utilisation comme herbicides
EP0531970A1 (fr) * 1991-09-11 1993-03-17 Sumitomo Chemical Company, Limited Composition herbicide
WO1998042703A1 (fr) * 1997-03-24 1998-10-01 Basf Aktiengesellschaft Derives de thiazolimine

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 119, no. 9, 30 August 1993, Columbus, Ohio, US; abstract no. 95515j, page 1098; XP002133217 *

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AU2435300A (en) 2000-08-01

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