+

WO1999019309A1 - 2,4-diamino-1,3,5-triazines substituees - Google Patents

2,4-diamino-1,3,5-triazines substituees Download PDF

Info

Publication number
WO1999019309A1
WO1999019309A1 PCT/EP1998/006124 EP9806124W WO9919309A1 WO 1999019309 A1 WO1999019309 A1 WO 1999019309A1 EP 9806124 W EP9806124 W EP 9806124W WO 9919309 A1 WO9919309 A1 WO 9919309A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
optionally substituted
given above
meanings given
diyl
Prior art date
Application number
PCT/EP1998/006124
Other languages
German (de)
English (en)
Inventor
Hans-Jochem Riebel
Hans-Joachim Dickershoff
Wolf-Rüdiger KOTYSCH
Stefan Lehr
Andreas Lender
Rolf Kirsten
Uwe Stelzer
Katharina Voigt
Ernst R. F. Gesing
Markus Dollinger
Toshio Goto
Yukiyoshi Watanabe
Original Assignee
Bayer Aktiengesellschaft
Nihon Bayer Agrochem K.K.
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, Nihon Bayer Agrochem K.K. filed Critical Bayer Aktiengesellschaft
Priority to AU10269/99A priority Critical patent/AU1026999A/en
Publication of WO1999019309A1 publication Critical patent/WO1999019309A1/fr

Links

Classifications

    • 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
    • C07D401/02—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 two hetero rings
    • C07D401/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the invention relates to new substituted 2,4-diamino-l, 3,5-triazines, several processes and new intermediates for their preparation and their use. As herbicides.
  • R 1 represents hydrogen or represents optionally substituted alkyl, alkylcarbonyl, alkoxycarbonyl, alkenylcarbonyl or alkynylcarbonyl,
  • R 2 stands for hydrogen or for optionally substituted alkenyl or alkynyl
  • R 3 stands for the grouping -AZ
  • A represents optionally substituted straight-chain or branched alkanediyl, which optionally contains a hetero atom (group) from the series oxygen, sulfur, imino (NH) or alkylimino (N-alkyl) at the beginning or at the end or within the alkanediyl chain , and
  • Z for an optionally substituted monocyclic or bicyclic, carbocyclic or heterocyclic grouping from the series cyclopentyl, cyclohexyl, phenyl, naphthyl, tetralinyl, decalinyl, indanyl, indenyl, furyl, benzofuryl, dihydrobenzofuryl, thienyl, benzothienyl,
  • Dihydrobenzothienyl isobenzo colryl, dihydroisobenzo colryl, isobenzothienyl, dihydroisobenzothienyl, pyrrolyl, indolyl, isoindolyl, indolinyl, isoindolinyl, benzdioxolyl, oxazolyl, benzoxazolyl, thiazolyl, benzothiazolyl, pyridazolyl, pyridazolyl, pyridazolyl Pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, cinnolinyl and phthalazinyl,
  • R 1 and R 3 have the meaning given above, and / or acid adducts of compounds of the general formula (II)
  • R 2 has the meaning given above and
  • X 1 represents halogen, alkoxy or the grouping -O-CO-R 2 ,
  • R 3 has the meaning given above and
  • L represents optionally substituted 2,2-bis-alkoxy-alkyl or the above for
  • R 2 has the meaning given, with alkylating or acylating agents of the general formula (V)
  • R 1 has the meaning given above with the exception of hydrogen and
  • X 2 represents halogen or the grouping -OR 1 , where R 1 with the exception of
  • 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 compounds of the general formula (I) also show insecticidal and acaricidal activity.
  • the compounds of the general formula (I) according to the invention optionally contain an asymmetrically substituted carbon atom and can in this case be present 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.
  • certain compounds of the formula (I) which contain alkenyl groups can exist as geometric (cis / trans) isomers or isomer mixtures.
  • 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
  • R 1 represents hydrogen, in each case optionally substituted by cyano, halogen or C1-C4-alkoxy alkyl, alkylcarbonyl or alkoxycarbonyl with up to 8 carbon atoms each, or for in each case optionally substituted by halogen alkenylcarbonyl or alkynylcarbonyl each with up to 8 carbon atoms,
  • R 2 represents hydrogen or alkenyl or alkynyl, each optionally substituted by halogen or C1-C4-alkoxy, each having up to 8 carbon atoms, and
  • R 3 stands for the grouping -AZ
  • A represents straight-chain or branched alkanediyl with 1 to 6 carbon atoms which is optionally substituted by cyano or halogen and which optionally contains a heteroatom (group) from the series oxygen, sulfur, imino at the beginning or at the end or within the alkanediyl chain Contains (NH) or C1-C4-alkylimino, and Z for an optionally substituted monocyclic or bicyclic, carbocyclic or heterocyclic grouping from the series cyclopentyl, cyclohexyl, phenyl, naphthyl, tetralinyl, decalinyl, indanyl, indenyl, furyl, benzofuryl, dihydrobenzo colryl, thienyl, benzothienyl, dihydrobenzobenzyl Isobenzothienyl, dihydroisobenzothienyl, pyrrolyl, indolyl, isoindolyl
  • Cyano or halogen substituted alkyl or alkoxy each having 1 to 6 carbon atoms each optionally substituted by halogen substituted alkylcarbonyl, alkoxycarbonyl, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms in the alkyl groups, each optionally by hydroxy, cyano, nitro, halogen, C1 -C4 alkyl, Cj-C ⁇ haloalkyl,
  • Ci -C4 haloalkoxy substituted phenyl or phenoxy, and in each case optionally substituted by halogen methylenedioxy or ethylenedioxy.
  • R 2 represents hydrogen or ethenyl, propenyl, butenyl which are optionally substituted by fluorine, chlorine and / or bromine, methoxy or ethoxy,
  • R 3 stands for the grouping -AZ
  • Phenoxy and in each case optionally substituted by fluorine and / or chlorine, methylenedioxy or ethylenedioxy.
  • 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.
  • R 2 has, for example, the meanings given below:
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1
  • R 2 has, for example, the meanings given above in Group 1
  • R 2 has, for example, the meanings given above in Group 1 Group 47
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • Group 98
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • Group 137
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1.
  • R 2 has, for example, the meanings given above in Group 1
  • Formula (II) provides a general definition of the substituted biguanides to be used as starting materials in process (a) according to the invention for the preparation of compounds of the formula (I).
  • R 1 and R 3 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 1 and R 3 .
  • 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).
  • R 3 has the meaning given above
  • R 1 has the meaning given above
  • reaction auxiliary such as hydrogen chloride
  • a diluent such as n-decane, toluene or 1,2-dichlorobenzene
  • R 2 preferably or in particular has the meaning which has already been mentioned above in Connection with the
  • X 1 preferably represents fluorine, chlorine, bromine, C -C4-alkoxy or the grouping -O-CO-R 2 , where R 2 preferably has the meaning given above, in particular X 1 represents chlorine, methoxy, ethoxy or acetoxy
  • the starting materials of the general formula (III) are known organic synthetic chemicals.
  • Formula (I), substituted triazines to be used as starting materials are generally defined by the formula (IV).
  • R 3 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 resp was given as being particularly preferred for R 3 ;
  • L preferably stands for 2,2-bis (C -C4-alkoxy) ethyl, in particular 2,2-bis-methoxy-ethyl or 2,2-bis-ethoxy-ethyl, or preferably or in particular has the meaning that was preferably given above or as particularly preferred for R 2 .
  • Formula (I), alkylating or acylating agents to be used as starting materials are generally defined by formula (V).
  • R 1 with the exception of hydrogen, 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 1 ;
  • X 2 preferably represents fluorine, chlorine, bromine, iodine, methoxy, ethoxy, acetoxy or propionyloxy, in particular chlorine, bromine, methoxy, ethoxy or acetoxy.
  • the starting materials of the general formula (V) are known synthetic chemicals.
  • reaction aids for processes (a) and (b). These preferably include alkali metal or alkaline earth metal acetates, amides, carbonates,
  • bicarbonates, hydrides, hydroxides or alkanolates such as, for example, sodium, potassium or calcium acetate, lithium, sodium, potassium or calcium amide, sodium, potassium or calcium carbonate, sodium, Potassium or calcium bicarbonate, lithium, sodium, potassium or calcium hydride, lithium, sodium, potassium or calcium hydroxide, sodium or potassium methoxide, - ethanolate, -n- or -i -propanolate, -n-, -i-, -s- or -t-butanolate; basic organic nitrogen compounds, such as trimethylamine, tri- ethylamine, tripropylamine, tributylamine, ethyl-diisopropylamine, N, N-dimethyl-cyclohexylamine, dicyclohexylamine, ethyl-dicyclohexylamine, N, N-dimethyl-aniline, N, N-dimethyl-benzylamine, pyridine, 2-methyl
  • 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, carbon tetrachloride; 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-dimethylace
  • Ethylene glycol monoethyl ether diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, their mixtures with water or pure water.
  • 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. To carry out the processes according to the invention, 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. 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.
  • the active compounds according to the invention can e.g. can be used in the following plants:
  • 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, rubber, oil palm, cocoa, berry fruit and hop plants, on ornamental and sports turf and pasture land and for selective purposes Weed control can be used 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 monocotyledons
  • 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, impregnated with active ingredients
  • formulations are prepared in a known manner, e.g. B. by mixing the active ingredients with extenders, that is liquid solvents and / or solid carriers, if appropriate using surface-active agents, that is
  • Emulsifiers and / or dispersants and / or foaming agents can, for example, also be used as auxiliary solvents.
  • auxiliary solvents can, for example, also be used as auxiliary solvents.
  • the following are essentially suitable as liquid 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, for example petroleum fractions, mineral and vegetable oils , Alcohols, such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methylhysobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • aromatics 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,
  • nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkyl aryl polyglycol ethers, alkyl sulfon
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, 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, for example iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes substances and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc are 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.
  • Cyhalofop (-butyl), 2,4-D, 2,4-DB, 2,4-DP, Desmedipham, Diallate, Dicamba, Diclofop (-methyl), Difenzoquat, Diflufenican, Dime roleson, Dimepiperate, Dimethachlor, Di- methametryn, dimethenamid, dinitramine, diphenamide, diquat, dithiopyr, diuron, dymron, EPTC, esprocarb, ethalfluralin, ethametsul Proceedingson (-methyl), etho colmesate, ethoxyfen, etobenzanid, fenoxaprop (-ethyl), flamprop (-isopropyliso, flamprop (-isopropyliso) - propyl-L), flamprop (-methyl), flazasulognion, fluazifop (-butyl), flumetsulam, flu
  • Insecticides Insecticides, acaricides, nematicides, bird repellants, plant nutrients and soil structure improvers are possible.
  • Solutions, suspensions, emulsions, powders, pastes and granules are used. 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.
  • the preparation and use of the active compounds according to the invention can be seen from the examples below.
  • Example (IV-1) for example, the compounds of the general formula (IV) listed in Table 2 below can also be prepared.
  • 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 are sprayed, which have a height of 5 to
  • 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 7, 13, 27 and 28 show with good tolerance to crop plants, such as e.g. Corn, strong activity against weeds (see Tables A-1 to A-3).

Landscapes

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

Abstract

L'invention concerne de nouvelles 2,4-diamino-1,3,5-triazines substituées de formule (I), dans laquelle R1 représente H, alkyle ou alkylcarbonyle, R2 représente H, alcényle ou alcynyle, R3 représente -A-Z, A désignant alcanediyle à chaîne linéaire ou ramifiée, éventuellement substitué, contenant éventuellement au début ou à la fin ou à l'intérieur de la chaîne alcanediyle, un hétéroatome (un groupe d'hétéroatomes) de la série oxygène, soufre, imino (NH) ou alkylimino (N-alkyle), et Z désignant un groupement monocyclique ou bicyclique, carbocyclique ou hétérocyclique, éventuellement substitué. L'invention concerne également un procédé et de nouveaux produits intermédiaires pour la production de ces composés et leur utilisation comme herbicide.
PCT/EP1998/006124 1997-10-10 1998-09-26 2,4-diamino-1,3,5-triazines substituees WO1999019309A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU10269/99A AU1026999A (en) 1997-10-10 1998-09-26 Substituted 2,4-diamino-1,3,5-triazines

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19744711.2 1997-10-10
DE1997144711 DE19744711A1 (de) 1997-10-10 1997-10-10 Substituierte 2,4-Diamino-1,3,5-triazine

Publications (1)

Publication Number Publication Date
WO1999019309A1 true WO1999019309A1 (fr) 1999-04-22

Family

ID=7845107

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1998/006124 WO1999019309A1 (fr) 1997-10-10 1998-09-26 2,4-diamino-1,3,5-triazines substituees

Country Status (3)

Country Link
AU (1) AU1026999A (fr)
DE (1) DE19744711A1 (fr)
WO (1) WO1999019309A1 (fr)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999052904A1 (fr) * 1998-04-09 1999-10-21 Bayer Aktiengesellschaft Thienylalkylamino-1,3,5-triazines et leurs utilisation comme herbicides
WO1999063822A1 (fr) * 1998-06-06 1999-12-16 Bayer Aktiengesellschaft Utilisation de 2,4-diamino-1,3,5-triazines substituées pour lutter contre les parasites animaux
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
EP1836894A1 (fr) 2006-03-25 2007-09-26 Bayer CropScience GmbH Nouvelles formulations solides à base de sulfonamides
EP1844654A1 (fr) 2006-03-29 2007-10-17 Bayer CropScience GmbH Activateur de la pénétration foliaire des principes actives agrochimiques
BG65251B1 (bg) * 1998-09-18 2007-10-31 Aventis Cropscience Gmbh Синергични комбинации от активни вещества за борба с нежелана растителност
DE102007013362A1 (de) 2007-03-16 2008-09-18 Bayer Cropscience Ag Penetrationsförderer für herbizide Wirkstoffe
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
US20190262497A1 (en) * 2016-09-13 2019-08-29 Carnegie Mellon University Therapeutic Acrylates as Enhanced Medical Adhesives
WO2024022502A1 (fr) * 2022-07-29 2024-02-01 江西天宇化工有限公司 COMPOSÉ BENZYL-TRIAZINE α-SUBSTITUÉ, SON PROCÉDÉ DE PRÉPARATION, SON UTILISATION ET HERBICIDE

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2014292193B2 (en) 2013-07-16 2018-04-26 Basf Se Herbicidal azines
EP3126348B1 (fr) 2014-04-03 2017-11-29 Basf Se Compose de diaminotriazine utile comme herbicide
EP2930174A1 (fr) 2014-04-07 2015-10-14 Basf Se Dérivés de diaminotriazine en tant qu'herbicides
US9822082B2 (en) 2014-04-11 2017-11-21 Basf Se Diaminotriazine derivatives as herbicides
EP3129359B1 (fr) 2014-04-11 2021-03-03 Basf Se Dérivés de diaminotriazine comme herbicides
WO2015162166A1 (fr) 2014-04-23 2015-10-29 Basf Se Composés de diaminotriazine et leur utilisation en tant qu'herbicides
US9822105B2 (en) 2014-04-23 2017-11-21 Basf Se Diaminotriazine compounds as herbicides
CN109983002A (zh) 2016-11-28 2019-07-05 巴斯夫欧洲公司 二氨基三嗪化合物
JP7111734B2 (ja) 2017-03-14 2022-08-02 ビーエーエスエフ ソシエタス・ヨーロピア 除草性アジン

Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3816419A (en) * 1972-10-27 1974-06-11 American Cyanamid Co Substituted s-triazines
US3932167A (en) * 1972-10-27 1976-01-13 American Cyanamid Company Substituted s-triazines as herbicidal agents
EP0191496A2 (fr) * 1985-02-15 1986-08-20 Idemitsu Kosan Company Limited Dérivés de triazine, procédé pour la préparation des dérivés et herbicides contenant les dérivés comme composant actif
EP0273328A2 (fr) * 1986-12-27 1988-07-06 Idemitsu Kosan Company Limited Dérivés de la triazine et herbicides les contenant
WO1990009378A1 (fr) * 1989-02-20 1990-08-23 Idemitsu Kosan Co. Ltd. Derive de triazine et herbicide le contenant a titre d'ingredient actif
WO1996025404A1 (fr) * 1995-02-17 1996-08-22 Idemitsu Kosan Co., Ltd. Derives de triazine
DE19522137A1 (de) * 1995-06-19 1997-01-02 Hoechst Schering Agrevo Gmbh 2-Amino-1,3,5-triazine, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren
WO1997008156A1 (fr) * 1995-08-24 1997-03-06 Hoechst Schering Agrevo Gmbh 2,4-diamino-1,3,5-triazines, leur procede de production et leur utilisation comme herbicides et regulateurs de la croissance de vegetaux
WO1998015536A1 (fr) * 1996-10-10 1998-04-16 Bayer Aktiengesellschaft 2,4-diamino-1,3,5-triazines substituees utilisees comme herbicides
WO1998015538A1 (fr) * 1996-10-10 1998-04-16 Bayer Aktiengesellschaft 2,4-diamino-1,3,5-triazines substituees utilisees comme herbicides
WO1998015539A1 (fr) * 1996-10-10 1998-04-16 Bayer Aktiengesellschaft 2-amino-4-alkylamino-1,3,5-triazines substituees utilisees comme herbicides
WO1998015537A1 (fr) * 1996-10-10 1998-04-16 Bayer Aktiengesellschaft 2-amino-4-alkylamino-1,3,5-triazines substituees utilisees comme herbicides

Patent Citations (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3816419A (en) * 1972-10-27 1974-06-11 American Cyanamid Co Substituted s-triazines
US3932167A (en) * 1972-10-27 1976-01-13 American Cyanamid Company Substituted s-triazines as herbicidal agents
EP0191496A2 (fr) * 1985-02-15 1986-08-20 Idemitsu Kosan Company Limited Dérivés de triazine, procédé pour la préparation des dérivés et herbicides contenant les dérivés comme composant actif
EP0273328A2 (fr) * 1986-12-27 1988-07-06 Idemitsu Kosan Company Limited Dérivés de la triazine et herbicides les contenant
WO1990009378A1 (fr) * 1989-02-20 1990-08-23 Idemitsu Kosan Co. Ltd. Derive de triazine et herbicide le contenant a titre d'ingredient actif
EP0411153A1 (fr) * 1989-02-20 1991-02-06 Idemitsu Kosan Company Limited Derive de triazine et herbicide le contenant a titre d'ingredient actif
WO1996025404A1 (fr) * 1995-02-17 1996-08-22 Idemitsu Kosan Co., Ltd. Derives de triazine
EP0810219A1 (fr) * 1995-02-17 1997-12-03 Idemitsu Kosan Company Limited Derives de triazine
DE19522137A1 (de) * 1995-06-19 1997-01-02 Hoechst Schering Agrevo Gmbh 2-Amino-1,3,5-triazine, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren
WO1997008156A1 (fr) * 1995-08-24 1997-03-06 Hoechst Schering Agrevo Gmbh 2,4-diamino-1,3,5-triazines, leur procede de production et leur utilisation comme herbicides et regulateurs de la croissance de vegetaux
WO1998015536A1 (fr) * 1996-10-10 1998-04-16 Bayer Aktiengesellschaft 2,4-diamino-1,3,5-triazines substituees utilisees comme herbicides
WO1998015538A1 (fr) * 1996-10-10 1998-04-16 Bayer Aktiengesellschaft 2,4-diamino-1,3,5-triazines substituees utilisees comme herbicides
WO1998015539A1 (fr) * 1996-10-10 1998-04-16 Bayer Aktiengesellschaft 2-amino-4-alkylamino-1,3,5-triazines substituees utilisees comme herbicides
WO1998015537A1 (fr) * 1996-10-10 1998-04-16 Bayer Aktiengesellschaft 2-amino-4-alkylamino-1,3,5-triazines substituees utilisees comme herbicides

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999052904A1 (fr) * 1998-04-09 1999-10-21 Bayer Aktiengesellschaft Thienylalkylamino-1,3,5-triazines et leurs utilisation comme herbicides
US6420313B1 (en) 1998-04-09 2002-07-16 Bayer Aktiengesellschaft Thienylalkylamino-1,3,5-triazines and the use thereof as herbicides
WO1999063822A1 (fr) * 1998-06-06 1999-12-16 Bayer Aktiengesellschaft Utilisation de 2,4-diamino-1,3,5-triazines substituées pour lutter contre les parasites animaux
BG65251B1 (bg) * 1998-09-18 2007-10-31 Aventis Cropscience Gmbh Синергични комбинации от активни вещества за борба с нежелана растителност
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
EP1836894A1 (fr) 2006-03-25 2007-09-26 Bayer CropScience GmbH Nouvelles formulations solides à base de sulfonamides
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
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
US20190262497A1 (en) * 2016-09-13 2019-08-29 Carnegie Mellon University Therapeutic Acrylates as Enhanced Medical Adhesives
US11292760B2 (en) * 2016-09-13 2022-04-05 Carnegie Mellon University Therapeutic acrylates as enhanced medical adhesives
WO2024022502A1 (fr) * 2022-07-29 2024-02-01 江西天宇化工有限公司 COMPOSÉ BENZYL-TRIAZINE α-SUBSTITUÉ, SON PROCÉDÉ DE PRÉPARATION, SON UTILISATION ET HERBICIDE

Also Published As

Publication number Publication date
AU1026999A (en) 1999-05-03
DE19744711A1 (de) 1999-04-15

Similar Documents

Publication Publication Date Title
WO1998015536A1 (fr) 2,4-diamino-1,3,5-triazines substituees utilisees comme herbicides
WO1999019309A1 (fr) 2,4-diamino-1,3,5-triazines substituees
DE19641691A1 (de) Substituierte 2-Amino-4-alkylamino-1,3,5-triazine
DE19641694A1 (de) Substituierte 2,4-Diamino-1,3,5-triazine
WO1999018100A1 (fr) 2,4-diamino-1,3,5-triazines substituees et leur utilisation comme herbicides
EP1049680A1 (fr) Aminoalkylidenaminotriazines substituees utilisees comme herbicides
DE19711825A1 (de) Substituierte 2,4-Diamino-1,3,5-triazine
EP1178985B1 (fr) Thienocycloalk(en)ylamino-1,3,5-triazines substituees
WO1999046249A1 (fr) Derives de 2,4-diamino-1,3,5-triazine substitues en position 6, comportant au moins deux atomes de carbone a substitution asymetrique, leur production et leur utilisation comme herbicides
EP1189893B1 (fr) 2-aryl-1,2,4-triazin-3,5-di(thi)ones substituees
EP1037882B1 (fr) 2,4-diamino-1,3,5-triazines substituees
DE19936633A1 (de) Substituierte Arylalkylamino-1,3,5-triazine
DE19812879A1 (de) Substituierte 2,4-Diamino-1,3,5-triazine
WO2000021938A1 (fr) Herbicides a base de formylaminotriazines substituees
DE19924370A1 (de) Substituierte Cyclohexylalkylamino-1,3,5-triazine
WO2000008000A1 (fr) Triazinones substituees utilisees comme herbicides
DE19933937A1 (de) Optisch aktive Thienylalkylamino-1,3,5-triazine
DE19937500A1 (de) Substituierte Heterocyclylbenzofurane
WO2000034257A1 (fr) 2-imino-thiazolines substituees et leur utilisation comme herbicides
DE19917160A1 (de) Disubstituierte Pyridine und Pyrimidine
DE19734664A1 (de) (Hetero)Aryloxypyrazole
EP1034168A1 (fr) Aryloxyalkylaminotriazines substituees
WO2000047579A1 (fr) Benzo-thiazolyl-alkylamino-1,3,5-triazines substituees utilisees comme herbicides
DE19704370A1 (de) Substituierte Benzoxazolyloxyacetanilide
DE19809360A1 (de) Optisch aktive substituierte 2,4-Diamino-1,3,5-triazine

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AL AM AT AU AZ BA BB BG BR BY CA CH CN CU CZ DE DK EE ES FI GB GD GE GH GM HR HU ID IL IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MD MG MK MN MW MX NO NZ PL PT RO RU SD SE SG SI SK SL TJ TM TR TT UA UG US UZ VN YU ZW

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): GH GM KE LS MW SD SZ UG ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN GW ML MR NE SN TD TG

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
REG Reference to national code

Ref country code: DE

Ref legal event code: 8642

NENP Non-entry into the national phase

Ref country code: KR

NENP Non-entry into the national phase

Ref country code: CA

122 Ep: pct application non-entry in european phase
点击 这是indexloc提供的php浏览器服务，不要输入任何密码和下载