EP0973754A1 - 2,4-diamino-1,3,5-triazines substituees utilisees comme herbicides - Google Patents

2,4-diamino-1,3,5-triazines substituees utilisees comme herbicides

Info

Publication number
EP0973754A1
EP0973754A1 EP98910739A EP98910739A EP0973754A1 EP 0973754 A1 EP0973754 A1 EP 0973754A1 EP 98910739 A EP98910739 A EP 98910739A EP 98910739 A EP98910739 A EP 98910739A EP 0973754 A1 EP0973754 A1 EP 0973754A1
Authority
EP
European Patent Office
Prior art keywords
compounds
hydrogen
halogen
formula
optionally substituted
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
EP98910739A
Other languages
German (de)
English (en)
Inventor
Hans-Jochem Riebel
Stefan Lehr
Uwe Stelzer
Markus Dollinger
Hans-Joachim Santel
Peter Dahmen
Toshio Goto
Yukiyoshi Watanabe
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
Bayer CropScience KK
Original Assignee
Bayer AG
Nihon Bayer Agrochem KK
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 AG, Nihon Bayer Agrochem KK filed Critical Bayer AG
Publication of EP0973754A1 publication Critical patent/EP0973754A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
    • A01N43/68—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms with two or three nitrogen atoms directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
    • C07D251/18—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom with nitrogen atoms directly attached to the two other ring carbon atoms, e.g. guanamines

Definitions

  • the invention relates to new substituted 2,4-diamino-l, 3,5-triazines, processes for their preparation and their use as herbicides.
  • R ⁇ represents (in each case unsubstituted) phenyl or naphthyl
  • R 2 represents alkyl
  • R ⁇ represents hydrogen, halogen or optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl,
  • R4 represents hydrogen, halogen or optionally substituted alkyl
  • R ⁇ represents hydrogen, halogen or optionally substituted alkyl
  • R6 stands for hydrogen or for optionally substituted alkyl, alkylcarbonyl or alkylsulfonyl,
  • R represents alkyl
  • Rl, R 2 , R-, R4 and R ⁇ have the meaning given above,
  • R has the meaning given above with the exception of hydrogen and X represents halogen, alkoxy, acyloxy or alkoxysulfonyloxy,
  • the new substituted 2,4-diamino-1,3,5-triazines of the general formula (I) are notable for their strong and selective herbicidal activity.
  • the 2,4-diamino-1,3,5-triazines of the general formula (I) according to the invention show good tolerance to crop plants, such as e.g. Barley and cotton, considerably more herbicidal activity than the previously known compound 2- amino-4- (1-phenyl-ethylamino) -6-trifluoromethyl-1,3,5-triazine.
  • the compounds of the general formula (I) according to the invention contain at least one asymmetrically substituted carbon atom and can therefore exist in various enantiomeric (R- and S-configured forms) or diastereomeric forms.
  • the invention relates both to the various possible individual enantiomeric or stereoisomeric forms of the compounds of the general formula (I) and to the mixtures of these isomeric compounds.
  • hydrocarbon chains such as alkyl - in each case in connection with heteroatoms, such as in alkoxy or alkylthio - are each straight-chain or branched.
  • Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.
  • the invention preferably relates to compounds of the formula (I) in which Rl stands for (respectively unsubstituted) phenyl or naphthyl,
  • R 2 represents alkyl having 1 to 6 carbon atoms
  • R ⁇ represents hydrogen, halogen or alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl, each of which has 1 to 6 carbon atoms and is optionally substituted by halogen or Cj- -i-alkoxy,
  • R4 represents hydrogen, halogen or Ci-Cg-alkyl which is optionally substituted by halogen,
  • R- > stands for hydrogen, for halogen or for C 1 -C 6 -alkyl optionally substituted by halogen, and
  • R6 represents hydrogen or Ci-Cg-alkyl, C2-C7-alkylcarbonyl or CI-C ⁇ -alkylsulfonyl which is optionally substituted by halogen or C1-C4-alkoxy,
  • the invention relates in particular to compounds of the formula (I) in which
  • Rl stands for (respectively unsubstituted) phenyl or naphthyl
  • R 2 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,
  • R ⁇ for hydrogen, for fluorine, chlorine, bromine, or for methyl, ethyl, n- or i-, each optionally substituted by fluorine, chlorine, methoxy or ethoxy
  • R4 represents hydrogen, fluorine, chlorine or bromine, or methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl which is optionally substituted by fluorine and / or chlorine,
  • R5 represents hydrogen, fluorine, chlorine or bromine, or methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl which is optionally substituted by fluorine and / or chlorine, and
  • R6 represents hydrogen or methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, acetyl, propionyl, n- or i-butyroyl which is optionally substituted by fluorine, chlorine, methoxy or ethoxy , Methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, n-, i-, s- or t-butylsulfonyl,
  • radical definitions listed above 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.
  • Formula (I) used as starting materials for substituted biguanides are generally defined by formula (II).
  • Rl, R 2 and R ⁇ preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention, preferably or as particularly preferred for Rl, R 2 and R ⁇ were specified.
  • Suitable acid adducts of compounds of the formula (II) are their addition products with protonic acids, such as e.g. with hydrogen chloride (hydrogen chloride), hydrogen bromide (hydrogen bromide), sulfuric acid, methanesulfonic acid, benzenesulfonic acid and p-toluenesulfonic acid.
  • protonic acids such as e.g. with hydrogen chloride (hydrogen chloride), hydrogen bromide (hydrogen bromide), sulfuric acid, methanesulfonic acid, benzenesulfonic acid and p-toluenesulfonic acid.
  • the starting materials of the general formula (II) are known and / or can be prepared by processes known per se (cf. US 3816419; Indian J. Chem. 1 (1963), 218-220; J. Am. Chem. Soc. 81 (1959), 3728-3736).
  • the substituted biguanides of the general formula (II) are obtained if amines of the general formula (V)
  • Rl and R 2 have the meaning given above
  • R6 has the meaning given above
  • reaction auxiliary e.g. Hydrogen chloride
  • a diluent e.g. n-Decane, toluene or 1,2-dichlorobenzene
  • alkoxycarbonyl compounds to be used further as starting materials in process (a) according to the invention for the preparation of compounds of the formula (I) are generally defined by the formula (III).
  • R 1, R 4 and R 5 preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention or as being particularly preferred for R 4, R 4 and R 4 were specified;
  • R preferably represents alkyl having 1 to 4 carbon atoms, in particular methyl or ethyl.
  • the starting materials of the formula (III) are known synthetic chemicals.
  • Formula (I) 2,4-diamino-1,3,5-triazines to be used as starting materials are generally defined by the formula (Ia).
  • Rl, R 2 , R ⁇ , R4 and R ⁇ preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention preferably or as particularly preferred for R. , R 2 , R ⁇ , R4 and R ⁇ were specified.
  • the starting materials of the general formula (Ia) are also the subject of the present application as new compounds; they can be prepared according to process (a).
  • Formula (IV) provides a general definition of the alkylating, acylating or sulfonylating agents which are further to be used as starting materials in process (b) according to the invention for the preparation of compounds of the formula (I).
  • R ⁇ preferably or in particular has the meaning which has already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention preferably or as particularly preferred for R ⁇ , with the exception of hydrogen;
  • X preferably represents fluorine, chlorine, bromine, iodine, methoxy, ethoxy, acetyloxy, propionyloxy, methoxysulfonyloxy or ethoxysulfonyloxy.
  • the starting materials of the general formula (VI) are known synthetic chemicals.
  • the processes according to the invention for the preparation of the compounds of the formula (I) are optionally carried out using a reaction auxiliary.
  • the usual inorganic or organic bases or acid acceptors are suitable as reaction aids for processes (a) and (b).
  • alkali metal or alkaline earth metal acetates, amides, carbonates, hydrogen carbonates, hydrides, hydroxides or alkanolates such as, for example, sodium, potassium or calcium acetate, lithium, sodium or 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, sodium or potassium methoxide, ethanolate, n or i propanolate, n, i, t or butanolate; also basic organic nitrogen compounds, such as trimethylamine, triethylamine, tripropylamine, tributylamine, ethyl diisopropylamine, N, N-dimethylcyclohexylamine, dicyclohexylamine, ethyl dicyclohexylamine, N, N-dimethylaniline, N, N- Dimethyl-benzylamine, pyridine,
  • Possible diluents for carrying out processes (a) and (b) according to the invention are inert organic solvents. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform,
  • Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones, such as methyl isopropyl ketone or methyl isobutyl ketone; Nitriles, such as acetonitrile, propionitrile or butyronitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; Esters such as methyl acetate or ethyl acetate; Sulfoxides, such as dimethyl sulfoxide, alcohols, such as methanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether, Ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monomethyl ether, di
  • 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 180 ° C, preferably between 10 ° C and 150 ° C.
  • Processes (a) and (b) according to the invention are generally carried out under atmospheric 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 in the presence of a reaction auxiliary and the reaction mixture is generally stirred at the required temperature for several hours.
  • the work-up is carried out using customary methods (cf. the manufacturing 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 understood to mean all plants that grow up 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.
  • the active compounds according to the invention can e.g. can be used in the following plants:
  • Pisum Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita.
  • Sorghum Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera.
  • the compounds are suitable for total weed control, e.g. on industrial and track systems and on paths and squares with and without tree cover.
  • the compounds for weed control in permanent crops e.g. Forest, ornamental wood, fruit, wine, citrus, nut,
  • Banana, coffee, tea, gum, oil palm, cocoa, berry fruit and hop plants are used on ornamental and sports turf and pasture land and for selective weed control in annual crops.
  • the compounds of formula (I) according to the invention are particularly 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 ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances and very fine encapsulations in polymeric substances.
  • formulations are prepared in a known manner, e.g. B. by mixing the active ingredients with extenders, ie liquid solvents and / or solid carriers, optionally using surface-active agents, ie 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 and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • alcohols such as butanol or glycol and their ethers and esters
  • ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
  • strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • 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,
  • Possible emulsifiers and / or foam-generating agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkyl aryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates;
  • Possible dispersing agents are, for example, lignin sulfite waste liquor and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins and synthetic phospholipids, can be used in the formulations.
  • 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.
  • Acetochlor Acifluorfen (-sodium), Aclonifen, Alachlor, Alloxydim (-sodium), Ametryne, Amidochlor, Amidosul possiblyon, Asulam, Atrazine, Azimsul possiblyon, Benazolin, Benfuresate, Bensulfuron (-methyl), Bentazon, Benzofenap, Benzoylprop Bialaphos, Bifenox, Bromobutide, Bromofenoxim, Bromoxynil, Butachlor, Butylate,
  • Triasul dueon tribenuron (-methyl), triclopyr, tridiphane, trifluralin and triflu- sul Resultson.
  • a mixture with other known active compounds such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents which improve soil structure, is also possible.
  • 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 customary manner, for example by watering, spraying, spraying or scattering.
  • 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.
  • a mixture of 27 g (0.21 mol) of 1-phenylethylamine (racemic), 22 ml of 33% aqueous hydrochloric acid and about the same amount of toluene is concentrated to dryness in a water jet vacuum.
  • 17 g (0.21 mol) of dicyanodiamide (cyanoguanidine) are added to the residue and the mixture is then heated at 150 ° C. for 2 hours, during which a melt is formed.
  • Example (II-1) Analogously to Example (II-1), it is also possible, for example, to prepare the compounds of the formula (II) listed in Table 2 below or their hydrochlorides.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • Seeds of the test plants are sown in normal soil. After about 24 hours, the soil with the active ingredient preparation is sprayed in such a way that the desired amounts of active ingredient are applied per unit area.
  • Spray liquor is chosen so that the desired amounts of active compound are applied in 1,000 l of water / ha.
  • 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
  • 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 in
  • the degree of damage to the plants is rated in% damage compared to the development of the untreated control.

Landscapes

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

Abstract

L'invention concerne de nouvelles 2,4-diamino-1,3,5-triazines substituées de la formule (I) dans laquelle R<1> désigne phényle ou naphtyle (non substitué dans chaque cas), R<2> désigne alkyle, R<3> désigne hydrogène, halogène ou alkyle, alcoxy, alkylthio, alkylsulfinyle ou alkylsulfonyle substitué dans chaque cas, R<4> désigne hydrogène, halogène ou alkyle éventuellement substitué, R<5> désigne hydrogène, halogène ou alkyle éventuellement substitué et R<6> désigne hydrogène ou alkyle, alkylcarbonyle ou alkylsulfonyle éventuellement substitué dans chaque cas, (le composé 2-amino-4-(1-phényle-éthylamino)-6-trifluorométhyle-1,3,5-triazine étant néanmoins exclu). L'invention concerne en outre des procédés de préparation de ces nouveaux composés et leur utilisation comme herbicides.
EP98910739A 1997-03-21 1998-03-09 2,4-diamino-1,3,5-triazines substituees utilisees comme herbicides Withdrawn EP0973754A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19711825 1997-03-21
DE19711825A DE19711825A1 (de) 1997-03-21 1997-03-21 Substituierte 2,4-Diamino-1,3,5-triazine
PCT/EP1998/001362 WO1998042684A1 (fr) 1997-03-21 1998-03-09 2,4-diamino-1,3,5-triazines substituees utilisees comme herbicides

Publications (1)

Publication Number Publication Date
EP0973754A1 true EP0973754A1 (fr) 2000-01-26

Family

ID=7824128

Family Applications (1)

Application Number Title Priority Date Filing Date
EP98910739A Withdrawn EP0973754A1 (fr) 1997-03-21 1998-03-09 2,4-diamino-1,3,5-triazines substituees utilisees comme herbicides

Country Status (7)

Country Link
US (1) US6399541B1 (fr)
EP (1) EP0973754A1 (fr)
JP (1) JP2001518104A (fr)
AU (1) AU723259B2 (fr)
CA (1) CA2284206A1 (fr)
DE (1) DE19711825A1 (fr)
WO (1) WO1998042684A1 (fr)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19810394A1 (de) * 1998-03-11 1999-09-16 Bayer Ag Substituierte Aminotriazine mit mindestens zwei asymmetrisch substituierten Kohlenstoffatomen
DE19825379A1 (de) * 1998-06-06 1999-12-09 Bayer Ag Verwendung von substituierten 2,4-Diamino-1,3,5-triazinen zur Bekämpfung tierischer Schädlinge
DE19842894A1 (de) * 1998-09-18 2000-03-23 Hoechst Schering Agrevo Gmbh Synergistische Wirkstoffkombinationen zur Bekämpfung von Schadpflanzen in Nutzpflanzenkulturen
EP1836894A1 (fr) 2006-03-25 2007-09-26 Bayer CropScience GmbH Nouvelles formulations solides à base de sulfonamides
EP1790227A1 (fr) 2005-11-25 2007-05-30 Bayer CropScience AG Suspensions aqueuses concentrées renferment des herbicides du group des 2,4-diamino-s-triazines
EP1844654A1 (fr) 2006-03-29 2007-10-17 Bayer CropScience GmbH Activateur de la pénétration foliaire des principes actives agrochimiques
DE102007013362A1 (de) 2007-03-16 2008-09-18 Bayer Cropscience Ag Penetrationsförderer für herbizide Wirkstoffe
DE102006059941A1 (de) 2006-12-19 2008-06-26 Bayer Cropscience Ag Substituierte 2,4-Diamino-1,3,5-triazine, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren
WO2011076731A1 (fr) 2009-12-23 2011-06-30 Bayer Cropscience Ag Formulation liquide de 2-iodo-n-[(4-méthoxy-6-méthyl-1, 3, 5-triazin-2-yl) carbamoyl] benzène sulfonamide
CN117466831A (zh) * 2022-07-29 2024-01-30 江西天宇化工有限公司 一种α-取代苄基-三嗪类化合物及其制备方法和应用、一种除草剂

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US3932167A (en) * 1972-10-27 1976-01-13 American Cyanamid Company Substituted s-triazines as herbicidal agents
US3816419A (en) 1972-10-27 1974-06-11 American Cyanamid Co Substituted s-triazines
JPS61189277A (ja) 1985-02-15 1986-08-22 Idemitsu Kosan Co Ltd トリアジン誘導体，その製造方法およびそれを有効成分とする除草剤
US4844731A (en) 1986-12-27 1989-07-04 Idemitsu Company Co., Ltd. Triazine derivatives
JPS63238071A (ja) * 1987-03-25 1988-10-04 Idemitsu Kosan Co Ltd トリアジン誘導体，その製造方法およびそれを含有する除草剤
DK0411153T3 (fr) 1989-02-20 1997-02-10 Idemitsu Kosan Co

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9842684A1 *

Also Published As

Publication number Publication date
US6399541B1 (en) 2002-06-04
DE19711825A1 (de) 1998-09-24
AU723259B2 (en) 2000-08-24
CA2284206A1 (fr) 1998-10-01
JP2001518104A (ja) 2001-10-09
AU6500498A (en) 1998-10-20
WO1998042684A1 (fr) 1998-10-01

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