EP1097146A1 - Verfahren zur herstellung von 2-amino-4-chlor-1,3,5-triazinen - Google Patents

Verfahren zur herstellung von 2-amino-4-chlor-1,3,5-triazinen

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Publication number
EP1097146A1
EP1097146A1 EP99932785A EP99932785A EP1097146A1 EP 1097146 A1 EP1097146 A1 EP 1097146A1 EP 99932785 A EP99932785 A EP 99932785A EP 99932785 A EP99932785 A EP 99932785A EP 1097146 A1 EP1097146 A1 EP 1097146A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
radicals
substituted
group
alkoxy
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Withdrawn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
EP99932785A
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German (de)
English (en)
French (fr)
Inventor
Jürgen Zindel
Jens Hollander
Klemens Minn
Lothar Willms
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
Original Assignee
Aventis CropScience GmbH
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Filing date
Publication date
Application filed by Aventis CropScience GmbH filed Critical Aventis CropScience GmbH
Publication of EP1097146A1 publication Critical patent/EP1097146A1/de
Withdrawn legal-status Critical Current

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    • 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
    • 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 the technical field of chemical synthesis of biologically active compounds, preferably the processes for the production of crop protection agents and intermediates for these processes.
  • 2-amino-chloro-1, 3,5-triazines which are substituted in position 6 on the triazine ring with organic radicals can be used to prepare biologically active aminotriazines, for example herbicidal aminotriazines, the chlorine atom being substituted by a N-substituted amino radical is exchanged; see.
  • the substituted 2-amino-4-chloro-1,3,5-triazines can be obtained according to a known process from the correspondingly substituted 2,4-dichloro-1,3,5-triazines and ammonia or amines [J. Med. Chem. 12 (1969) 41, J. Am. Chem. Soc. 82 (1960) 3760].
  • the 6-substituted 2,4-dichloro-1,3,5-triazines used as starting compounds for this purpose can be prepared, for example, from cyanuric chloride and Grignard compounds which are substituted according to the organic radical in position 6 on the triazine ring [Helv. Chim. Acta 33 (1950) 1368].
  • they can be synthesized from trichloromethyl isocyanide dichloride and amidines which are substituted according to the organic radical in position 6 on the triazine ring (cf. DE-A-1178437).
  • the invention has for its object to produce 2-amino-4-chloro-1, 3,5-triazines with optionally substituted aliphatic hydrocarbon radicals at the 6-position in an alternative and preferably advantageous manner. This is intended to make novel triazines of the formula (I) accessible in some cases.
  • the invention relates to a process for the preparation of compounds of the formula (I) or their salts,
  • R 1 (C ⁇ C ⁇ Jalkyl or (C 3 -C 8 ) cycloalkyl, each of the two radicals above being independently unsubstituted or substituted, preferably unsubstituted or by one or more radicals from the group consisting of halogen, hydroxy, cyano , Nitro, thiocyanato, formyl, (CrC ⁇ Jalkoxy, (d-C ⁇ Jalkylthio, (CVC alkylsulfinyl, (CVC ⁇ Jalkylsulfonyl, [(C, -C 8 ) alkyl] carbonyl, [(C r C 8 ) alkoxy] carbonyl, (C 2 - C 8 ) alkenyl, (C 2 -C 8 ) alkynyl, (C 3 -C 8 ) cycloalkyl, phenyl and in the case of cycloalkyl also (C 1 -C 8 ) alkyl,
  • R 2 , R 3 each independently of one another hydrogen, amino, hydroxyl, formyl or optionally substituted (CVC ⁇ alkyl, (C 1 -C 8 ) alkylamino, di [(C C 8 ) alkyl] amino, (C r C 8 ) alkyloxy, aryl, aryloxy, (C 3 -C 8 ) cycloalkyl, [(C r C 8 ) alkyl] carbonyl, [(C C ⁇ J alkoxyJcarbonyl, arylcarbonyl, aryloxycarbonyl, (C ⁇ C ⁇ JAlkylsulfonyl, arylsulfonyl or an optionally substituted heterocyclyl radical, heterocyclyloxy radical, heterocyclylamino radical each having 3 to 6 ring atoms and 1 to 3 hetero ring atoms from the group N, O and S or
  • R 2 , R 3 together with the nitrogen atom of the group NR 2 R 3 are a heterocyclic radical with 3 to 6 ring atoms and 1 to 4 hetero ring atoms, wherein in addition to the N atom the optionally further hetero ring atoms are selected from the group N, O and S and the heterocycle is optionally substituted, characterized in that 2-amino-4-thio-1, 3,5-triazines of the general
  • X is hydrogen, (C r C 6 ) alkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl or phenyl, each of the latter 4 radicals being unsubstituted or substituted, or one via sulfur bound equally substituted 2-amino-4-thio-1, 3,5-triazine radical is converted into the compound (I) by chlorination.
  • the 2-amino-4-thio-1,3,5-triazines (II) serving as starting materials are known or can be prepared analogously to known processes [cf. DE-A-4139624, Chem. Ber. 100 (1967) 1874-1891, J. Heterocyclic Chem. 27 (1990) 1565-1568, J. Heterocyclic Chem. 23 (1986) 1709-1714].
  • the chlorinating agent is used, for example, in amounts of 1 to 100 equivalents based on the compound of the formula (II), preferably 1 to 10 equivalents, in particular equimolar to an excess, in which a reaction of the compound of the formula (II) is possible.
  • the equivalent is the amount of the chlorinating agent which is required for the reaction of the compound (II) after the stoichiometry of the reaction.
  • the chlorination can be carried out without additional solvent and / or diluent (hereinafter collectively: solvent) or, in most cases, expediently in the presence of a solvent.
  • solvent preferably organic solvents which are largely inert under the reaction conditions for the chlorinating agent and for the compounds of the formulas (II) and (I).
  • Suitable solvents are, for example:
  • Reaction conditions are inert, for example aliphatic and aromatic hydrocarbons, such as. B. mineral oils, petroleum ether, cyclohexane or toluene, xylenes, naphthalene derivatives, ⁇ Solvesso 200 (high-boiling aromatic mixture); halogenated aliphatic and aromatic hydrocarbons, such as methylene chloride, dichloroethane, chloroform or chlorobenzene; cyclic or open-chain ethers, such as diethyl ether, di-n-propyl ether, diisopropyl ether, methyl tert-butyl ether, tetrahydrofuran (THF), dioxane, alkylene glycol monoalkyl ether and dialkyl ether such as, for.
  • aliphatic and aromatic hydrocarbons such as. B. mineral oils, petroleum ether, cyclohexane or toluene, xylenes, na
  • B propylene glycol monomethyl ether, propylene glycol monoethyl ether, ethylene glycol monomethyl ether or monoethyl ether, dimethoxyethane, diglyme, triglyme and tetraglyme; Amides such as dimethylformamide (DMF), dimethylacetamide and N- Methyl pyrrolidone;
  • Ketones such as cyclohexanone, methyl isobutyl ketone (MIBK);
  • Nitriles such as acetonitrile, propionitrile, butyronitrile and benzonitrile
  • Sulfoxides and sulfones such as dimethyl sulfoxide (DMSO) and sulfolane,
  • Carboxylic acid esters such as the esters of mono-, di- and tricarboxylic acids with aliphatic alcohols with 1 to 10 carbon atoms, for example
  • protic solvents are aliphatic alcohols, such as methanol, ethanol, n- or i-propanol, n-, i-, sec- or tert-butanol, glycols;
  • Carboxylic acids e.g. B. those with 1 to 4 carbon atoms such as formic acid, acetic acid, n-propionic acid or n- and isobutanoic acid.
  • chlorination of compounds of the formula (II) is carried out with chlorine, for example methylene chloride, chloroform and concentrated acetic acid, preferably corresponding anhydrous solvents such as e.g. Glacial acetic acid, particularly suitable as a solvent.
  • chlorine for example methylene chloride, chloroform and concentrated acetic acid, preferably corresponding anhydrous solvents such as e.g. Glacial acetic acid, particularly suitable as a solvent.
  • the reaction can be in a wide temperature range, partly as a function of substrate, chlorinating agent and solvent, for example at temperatures between -40 C C and the boiling temperature of the respective solvent, preferably between -20 ° C and 100 ° C, in particular between 0 ° C and 50 ° C are carried out.
  • the reaction temperature should be set as low as possible to avoid side reactions, but so high that implementation in technically justifiable response times is possible.
  • reaction mixture for example, inert gas, e.g. B. nitrogen gas through the mixture to remove excess chlorine gas, and then add the reaction mixture to water.
  • inert gas e.g. B. nitrogen gas
  • the product is separated from the water and dried.
  • the reaction mixture is preferably added to an aqueous solution of a base.
  • a base which is insoluble in this solvent, filtered and the product is separated from the solvent and dried.
  • Suitable bases are conventional organic and preferably inorganic bases and their aqueous solutions, for example hydroxides or carbonates of alkali metals or alkaline earth metals.
  • reaction conditions for chlorination mentioned in the known regulations cannot easily be transferred to the 2-amino-4-thio-1,3,5-triazines of the formula (II) with optionally substituted alkyl radicals at the 6-position.
  • the alkylthio-1,3,5-triazines used according to the invention with optionally substituted aliphatic radicals in the 6-position generally require milder chlorination conditions.
  • the amino group at the 2-position can in some cases lead to undesired side reactions and thus to losses in yield or lower product purities.
  • the radical R 1 preferably has the following meaning: R 1 (CC 6 ) alkyl which is unsubstituted or by one or more radicals from the group consisting of halogen, Hydroxy, cyano, nitro, thiocyanato, formyl, (C ⁇ C alkoxy, (C ⁇ C ⁇ alkylthio, (C r C 4 ) alkylsulfinyl, (dC ⁇ alkylsulfonyl, [(C r C 4 ) alkyl] carbonyl, [(C 1 -C 4 ) alkoxy] carbonyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, (C 3 - C 6 ) cycloalkyl, phenyl, each of the last 10 radicals being unsubstituted or by one or more Residues from the radicals from the radicals from the radicals from the group consisting of halogen, Hydr
  • R 1 is preferably also (C 3 -C 6 ) cycloalkyl which is unsubstituted or by one or more radicals from the group consisting of halogen, hydroxy, cyano, nitro, thiocyanato, formyl, (C r C 4 ) alkyl, (C r C 4 ) alkoxy, (C r C 4 ) alkylthio, (C r C 4 ) alkylsulfinyl, (C 1 -C 4 ) alkylsulfonyl, [(C r C 4 ) alkyl] carbonyl, [(C r C 4 ) alkoxy ] carbonyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, (C 3 -C 6 ) cycloalkyl, phenyl, each of the latter 11 residues being unsubstituted or by one or more residues from the group consisting of
  • R 1 is particularly preferred (C 1 -C 4 alkyl which is unsubstituted or substituted by one or more radicals from the group halogen, preferably fluorine, chlorine or bromine, hydroxyl, methoxy, ethoxy and cyclopropyl.
  • halogen preferably fluorine, chlorine or bromine, hydroxyl, methoxy, ethoxy and cyclopropyl.
  • R 1 is particularly preferably also (C 3 -C ⁇ ) cycloalkyl which is unsubstituted or by one or more radicals from the group halogen, preferably fluorine, chlorine or bromine, hydroxy, (C 1 -C 4 ) alkoxy, preferably methoxy and Ethoxy, (C 1 -C 4 ) alkyl, preferably methyl and ethyl, and (C r C 4 ) haloalkyl, preferably CF 3 , is substituted.
  • halogen preferably fluorine, chlorine or bromine
  • R 2 , R 3 are preferably each independently of one another hydrogen, amino, (C r C 6 ) alkyl, (C 1 -C 4 ) alkylamino, di [(C r C 4 ) alkyl] amino, (C r C 4 ) alkyloxy , (C 3 -C 6 ) cycloalkyl, (C 1 -C 4 ) alkyl] carbonyl, [(C 1 -C 4 ) alkoxy] carbonyl, phenylcarbonyl, phenoxycarbonyl, (C 1 -C 4 alkylsulfonyl, phenylsulfonyl or a heterocyclyl radical with 3 to 6 ring atoms and 1 to 3 hetero ring atoms from the group N, O and S, phenyl in the abovementioned radicals or the heterocyclyl radical independently of one another unsubstituted or by one or more radicals from the group halogen, preferably fluorine,
  • R 2 , R 3 together with the nitrogen atom of the group NR 2 R 3 are a heterocyclic radical with 3 to 6 ring atoms and 1 to 3 hetero ring atoms, wherein in addition to the N atom the optionally further hetero ring atoms are selected from the group N, O and S and the heterocycle is unsubstituted or by one or more radicals from the group halogen, preferably fluorine, chlorine or bromine, hydroxy, (C 1 -C 4 ) alkoxy, preferably methoxy and ethoxy, (C r C 4 ) alkyl, preferably methyl and ethyl, and (C r C 4 ) haloalkyl, preferably CF 3 , is substituted.
  • halogen preferably fluorine, chlorine or bromine
  • hydroxy preferably methoxy and ethoxy
  • C r C 4 ) alkyl preferably methyl and ethyl
  • the radicals R 2 , R 3 are each independently of one another preferably hydrogen, amino, methyl, ethyl, acetyl.
  • the compounds of the formula (I) can form salts by addition of a suitable inorganic or organic acid, for example HCl, HBr, H 2 SO 4 or HNO 3 , but also oxalic acid or sulfonic acids to a basic group, such as amino or alkylamino.
  • radical X has the following meaning, for example:
  • X stands for example for hydrogen, (C ⁇ C ⁇ alkyl, (C 2 -C 6 ) alkenyl or (C 2 - C 6 ) alkynyl, each of the latter 3 radicals unsubstituted or by one or more radicals from the group consisting of Halogen, (C ⁇ C ⁇ alkoxy, (C, -C 4 ) alkylthio, (C r C 4 ) alkylsulfinyl, (C r C 4 ) alkylsulfonyl, [(C 1 -C 4 ) alkyl] carbonyl, [(C r C 4 ) alkoxy] carbonyl, (C 3 -C 6 ) cycloalkyl and phenyl, each of the last 10 radicals being unsubstituted or by one or more radicals from the group consisting of halogen, (C 1 -C 4 ) alkoxy, (C ⁇ C alkylthio and in the case of
  • X preferably represents (C 1 -C 4 ) alkyl which is unsubstituted or by one or more radicals from the group consisting of halogen, (C 1 -C 4 ) alkoxy, (CC 4 ) alkylthio, (C 3 -C 6 ) Cycloalkyl and phenyl, each of the latter 4 residues being unsubstituted or by one or more residues from the group consisting of halogen, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylthio and in the case of cyclic residues also (C r C 4 ) alkyl and (C 1 -C 4 ) haloalkyl is substituted, is substituted, or for phenyl which is unsubstituted or by one or more radicals from the group halogen, cyano, nitro, (CC 4 ) alkyl, (C r C 4 ) haloalkyl, (C 1 -
  • X stands in particular for (C 1 -C 4 ) alkyl, benzyl or phenyl, each of the latter two groups in the phenyl part being unsubstituted or by one or more radicals from the group halogen, cyano, nitro, (C 1 -C 4 alkyl, preferably methyl) , (C ⁇ C haloalkyl, preferably CF 3 or CCI 3 , (C ⁇ C ⁇ alkoxy, preferably methoxy, (CC 4 ) haloalkoxy, preferably OCHF 2 , and (CC 4 ) alkylthio.
  • alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino and alkylthio radicals and the corresponding unsaturated and / or substituted radicals in the carbon skeleton can each be straight-chain or branched.
  • the lower carbon skeletons e.g. with 1 to 6 carbon atoms or in the case of unsaturated groups with 2 to 6 carbon atoms, preferred.
  • Alkyl radicals also in the composite meanings such as alkoxy, haloalkyl etc., mean e.g.
  • Alkynyl means e.g. Propargyl, but-2-in-1-yl, but-3-in-1-yl, 1-methyl-but-3-in-1-yl.
  • Cycloalkyl means a carbocyclic, saturated ring system with preferably 3-8 C atoms, for example cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
  • Halogen means, for example, fluorine, chlorine, bromine or iodine.
  • Haloalkoxy is, for example, OCF 3 , OCHF 2 , OCH 2 F, CF 3 CF 2 O, OCH 2 CF 3 and OCH 2 CH 2 CI; The same applies to haloalkenyl and other halogen-substituted radicals.
  • Aryl means a mono-, bi- or polycyclic aromatic system, for example phenyl, naphthyl, tetrahydronaphthyl, indenyl, indanyl, pentalenyl, fluorenyl and the like, preferably phenyl.
  • a heterocyclic radical or ring can be saturated, unsaturated or heteroaromatic; it preferably contains one or more, in particular 1, 2 or 3, heteroatoms in the heterocyclic ring, preferably from the group N, O, and S; it is preferably an aliphatic heterocyclyl radical with 3 to 7 ring atoms or a heteroaromatic radical with 5 or 6 ring atoms.
  • the heterocyclic residue can e.g. be a heteroaromatic residue or ring (heteroaryl), e.g.
  • a mono-, bi- or polycyclic aromatic system in which at least 1 ring contains one or more heteroatoms for example pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, thienyl, thiazolyl, thiadiazolyl, oxazolyl, isoxazolyl, furyl, pyrrolyl, pyrazolyl and imidazolyl , or is a partially or fully hydrogenated radical such as oxiranyl, pyrrolidyl, piperidyl, piperazinyl, dioxolanyl, oxazolinyl, isoxazolinyl, oxazolidinyl, isoxazolidinyl, morpholinyl, tetrahydrofuryl.
  • heteroatoms for example pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, tri
  • Possible substituents for a substituted heterocyclic radical are the substituents mentioned below, and additionally oxo.
  • the oxo group can also be attached to the hetero ring atoms, which can exist in different oxidation states, e.g. at N and S, occur.
  • Substituted radicals such as a substituted alkyl, alkenyl, alkynyl, aryl, phenyl, Benzyl, heterocyclyl and heteroaryl radicals mean, for example, a substituted radical derived from the unsubstituted base body, the substituents being, for example, one or more, preferably 1, 2 or 3, radicals from the group halogen, alkoxy, haloalkoxy, alkylthio, hydroxy, amino, nitro, Carboxy, cyano, azido, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, mono- and dialkylaminocarbonyl, substituted amino such as acylamino, mono- and dialkylamino, and alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl and, in the case of cyclic radicals,
  • radicals with carbon atoms those with 1 to 4 carbon atoms, in particular 1 or 2 carbon atoms, are preferred.
  • the formulas (I) and (II) also include all stereoisomers. Such compounds contain one or more asymmetric carbon atoms or double bonds, which are not specified separately in the general formulas.
  • the possible stereoisomers defined by their specific spatial shape, such as enantiomers, diastereomers, Z and E isomers, can be obtained from mixtures of the stereoisomers by customary methods or can also be prepared by stereoselective reactions in combination with the use of stereochemically pure starting materials.
  • the compounds (I) are preferably replaced by exchanging the chlorine atom with amines of the formula (III) A-NH-R (III)
  • radicals R ⁇ R 2 , R 3 are as defined in formula (I) and A and R are radicals which, in conjunction with the residual molecular structure of the formula (IV), the chemical structure of a represent herbicidally active aminotriazine.
  • the herbicidal aminotriazines are preferably those from the publications WO-A-90/09378, WO-A-96/25404, WO-A-97/00254, WO-A-97/08156, WO-A-97 / 19936, WO-A-97/29095, WO-A-97/31904, WO-A-97/35481, WO-A-98/10654, WO-A-98/15536, WO-A-98/15537 , WO-A-98/15538, WO-A-98/15539, International Application No. PCT / EP98 / 00283 and German Patent Application No. 19826670.7, but with the residues R 2 and R 3 according to the above-mentioned invention Procedures are defined. Specific reference is made here to the definition of the herbicidal aminotriazines from the publications; they are therefore part of the present description.
  • the radical A is preferably a (C 1 -C 4 alkylene chain which is substituted in the ⁇ -position to the amino group by an unsubstituted or substituted alkyl radical and in the ⁇ -position by an optionally substituted aryl, heteroaryl, aryloxy or heteroaryloxy radical and which may have further substituents from the group halogen, alkyl, alkoxy and hydroxy.
  • R is preferably H or alkyl such as (C 1 -C 4 ) alkyl, in particular H.
  • herbicidal aminotriazines listed in the publications mentioned, in particular the compounds which are each specifically defined, such as the preparation examples and the individually defined table examples, insofar as they correspond to the radicals R 1 , R 2 and R 3 in formula (IV) Residues are defined in the context of the present invention.
  • the invention therefore also relates to a process for the preparation of herbicidal aminotriazines of the formula (IV), characterized in that a compound of the formula (I) is first prepared according to the invention and then with an amine of the formula (III) to give the compound of the formula (IV ) implements.
  • Reaction conditions for the reaction of the compounds of the formulas (I) and (III) are known in principle from the publications cited for the herbicidal aminotriazines (IV) and the literature cited therein, or can be carried out analogously to the standard reactions which are known in the art for the reaction of heteroaromatic chlorine compounds with amines become..
  • the invention generally relates to the use of compounds of the formula (I) or their salts, which have been obtained by the process according to the invention for the preparation of the compounds (I), for the production of biologically active compounds from the chemical class of aminotriazines, preferably the herbicidal aminotriazines.
  • Chlorine gas was introduced at 20 to 25 ° C. into a solution of 21 g of 2-amino-4-methylthio-6-trifluoromethyl-1, 3,5-triazine in 0.2 l of glacial acetic acid (15 min).
  • the reaction mixture was stirred at approx. 20 ° C. for 30 min, flushed with nitrogen gas at room temperature for 1 h, added to 1 l of ice-cold aqueous solution of 70 g of sodium hydroxide and stirred for 5 min. After extraction with ethyl acetate, the organic phase was washed with water, dried over magnesium sulfate and the solvent i. Vak. away.
  • the crude product was purified by stirring in heptane.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
EP99932785A 1998-07-10 1999-07-02 Verfahren zur herstellung von 2-amino-4-chlor-1,3,5-triazinen Withdrawn EP1097146A1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19830902A DE19830902A1 (de) 1998-07-10 1998-07-10 Verfahren zur Herstellung von 2-Amino-4-chlor-1,3,5-triazinen
DE19830902 1998-07-10
PCT/EP1999/004581 WO2000002868A1 (de) 1998-07-10 1999-07-02 Verfahren zur herstellung von 2-amino-4-chlor-1,3,5-triazinen

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EP1097146A1 true EP1097146A1 (de) 2001-05-09

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US (1) US7002011B1 (pt)
EP (1) EP1097146A1 (pt)
JP (1) JP2002520321A (pt)
CN (1) CN1155582C (pt)
AU (1) AU4904899A (pt)
BR (1) BR9911975A (pt)
DE (1) DE19830902A1 (pt)
HU (1) HUP0105180A3 (pt)
RU (1) RU2271353C2 (pt)
WO (1) WO2000002868A1 (pt)
ZA (1) ZA200006795B (pt)

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HUE031444T2 (en) 2012-10-24 2017-07-28 Basf Se Herbicide azines
CN105555779B (zh) 2013-07-16 2019-05-10 巴斯夫欧洲公司 除草的嗪类
US20170144985A1 (en) 2014-04-03 2017-05-25 Basf Se Diaminotriazine compound useful as herbicide
EP2930174A1 (en) 2014-04-07 2015-10-14 Basf Se Diaminotriazine derivatives as herbicides
EP3129359B1 (en) 2014-04-11 2021-03-03 Basf Se Diaminotriazine derivatives as herbicides
BR112016023556B1 (pt) 2014-04-11 2021-05-25 Basf Se composto diaminotriazina, composição agroquímica, método para controlar vegetação indesejada e uso de um composto
WO2015162166A1 (en) 2014-04-23 2015-10-29 Basf Se Diaminotriazine compounds and their use as herbicides
EA201692129A1 (ru) 2014-04-23 2017-03-31 Басф Се Диаминотриазины в качестве гербицидов

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DE19830902A1 (de) 2000-01-13
RU2001103751A (ru) 2003-02-10
HUP0105180A3 (en) 2004-03-01
RU2271353C2 (ru) 2006-03-10
ZA200006795B (en) 2002-02-21
WO2000002868A1 (de) 2000-01-20
HUP0105180A2 (hu) 2002-04-29
US7002011B1 (en) 2006-02-21
JP2002520321A (ja) 2002-07-09
AU4904899A (en) 2000-02-01
CN1306518A (zh) 2001-08-01
BR9911975A (pt) 2001-03-27
CN1155582C (zh) 2004-06-30

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