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公开(公告)号:CA1171098A
公开(公告)日:1984-07-17
申请号:CA381429
申请日:1981-07-09
Applicant: DEGUSSA
Inventor: KLEEMANN AXEL , SCHWARZE WERNER , REMMEL HANS , HOHN WOLFGANG
IPC: C07C231/02 , C07C67/00 , C07C231/00 , C07C231/14 , C07C233/00 , C07C233/58 , C07C103/19
Abstract: Cyclopropyl carboxylic amides are interesting intermediate products particularly for the production of the corresponding amines, which are in turn a basis for herbicides. According to the present invention the cyclopropyl carboxylic amides are produced by reacting .gamma.-chloro butyric esters with alcoholates in the presence of liquid ammonia. The products are obtained in high yields.
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公开(公告)号:MX5454E
公开(公告)日:1983-08-10
申请号:MX726778
申请日:1978-07-18
Applicant: CIBA GEIGY AG , DEGUSSA
Inventor: FISSIOTAS GEORG , MEYER WILLY , SCHWARZE WERNER , KLENK HERBERT , LEUCHTENBERGER WOLFGANG
IPC: A01N43/707 , A01P13/00 , C07D253/075 , C07D253/06
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公开(公告)号:CH625513A5
公开(公告)日:1981-09-30
申请号:CH1499875
申请日:1975-11-19
Applicant: DEGUSSA
Inventor: BITTNER FRIEDRICH , SUCHSLAND HELMUT , SCHREYER GERD , SCHWARZE WERNER , HASCHKE HEINZ
IPC: C07D251/28
Abstract: There is provided a process for the production of a solution or suspension of cyanuric chloride in a water containing organic solvent wherein the liquid cyanuric chloride and the organic-aqueous solvent are mixed together while being agitated, the liquid cyanuric chloride at a temperature between its melting point and 200 DEG C. is led into the flowing organic-aqueous solvent with a velocity of Vcy (in kg per hour) wherein where P is the desired concentration of cyanuric chloride in the solution or suspension to be produced in weight %, PLM is the concentration of cyanuric chloride in the solvent used which also includes O, VLM is the velocity of the solvent added in kg/h, AND PLM, VLM and TLM, the temperature of the added solvent, are so selected that the expression does not exceed the boiling temperature in DEG C. of the solvent used and wherein Cp(LM) and Cp(Cy) signify the specific heat capacities in cal. x g 1 x ( DEG degree C) 1 of the solvent and cyanuric chloride respectively, whereupon in a given case within at most 3 minutes after bringing the cyanuric chloride and solvent into contact the flowing mixture is cooled to the desired storage temperature.
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公开(公告)号:RO76667A
公开(公告)日:1981-04-30
申请号:RO8475876
申请日:1976-02-11
Applicant: DEGUSSA
Inventor: HASCHKE HEINZ , SCHREYER GERD , SCHWARZE WERNER , SUCHSLAND HELMUT
IPC: C07D251/50 , C07D251/44 , C07D251/40
Abstract: There is provided a process, preferably continuous and in a given case successive, substitution of one or two chlorine atoms of cyanuric chloride by one or two amines, which may be the same or different, in the presence of an acid acceptor and in the presence of an organic solvent, particularly for the production of 2-alkylamino-4,6-dichloro and preferably for the production of 2,4-di(alkylamino)-6-chloro-s-triazines wherein there is added 1.00 to 1.05 mole, preferably 1.00 to 1.03 mole of a first amine to a 4.5 to 50 weight % suspension or solution of cyanuric chloride in a mixture of 65 to 85 weight % of xylene, toluene, ethylbenzene, benzene and/or an aliphatic or cycloaliphatic hydrocarbon with 5 to 10 carbon atoms (toluene being preferred) and 35 to 15 weight % of a ketone with 3 to 8 carbon atoms, preferably acetone, while maintaining the temperature between about 0 and about 20 DEG C, preferably about 10 to 18 DEG C., continuously so regulating the pH value of the reaction mixture obtained in accordance with the reaction time by addition of alkali and in a given case, water so that this corresponds to a point within the area bounded by lines ABCD of FIG. 1, which runs through the area beginning with the reaction time t,(step 1)= 0 until reaching a position in the area bounded by the lines BCEF and after reaching a pH of 7.0, preferably 7.2 maintains a temperature of about 10 DEG to about 60 DEG C., preferably about 25 DEG to 40 DEG C., after addition of 0.96 to 1.05, preferably 0.98 to 1.02 equivalents of alkali per mole of cyanuric chloride, adding at least an equimolar amount, preferably 1.00 to 1.02 mole of the second amine per mole of cyanuric chloride and continuously so adjusting the pH value of the reaction mixture obtained depending on the reaction time by addition of alkali that this corresponds to a point within the area which is defined by lines GHIJ in FIG. 3 which passes through the band beginning with the reaction time t(step 2)= 0 of the second reaction step until reaching a position in the area bounded by the lines HIKL and thereby maintaining a temperature of 40 to 70 DEG C., preferably 45 DEG to 55 DEG C. and thereafter working up the product in known manner wherein t1 is a time of 4 to 10 hours, preferably about 7 hours and t2 is a time of 2 to 8 hours, preferably about 6 hours and wherein the B C corresponds to the equation, pH = -(12.6/t1)+ 14.35 and the line H I corresponds to the equation pH = -(24,857/t2)+ 23.9285. There are also disclosed novel, purified mono and bis alkylamino-cyanoalkylalkylamino - s - triazines.
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公开(公告)号:DD137225A5
公开(公告)日:1979-08-22
申请号:DD20678978
申请日:1978-07-18
Applicant: DEGUSSA
Inventor: KLENK HERBERT , SCHWARZE WERNER , LEUCHTENBERGER WOLFGANG
IPC: C07D253/06 , A01N43/707 , C07D253/075
Abstract: 1,2,4-triazin-5-one compounds of the general formula (I) (I) where R is are prepared by reacting a compound of general formula (II) (II) in which R is defined above with either (a) a tertiary alcohol of general formula (III) HO-R'(III) in which R' is a t-alkyl group having 4 to 18 carbon atoms, especially t-amyl or t-octyl or preferably t-butyl or (b) an alkene of general formula (IV) (IV) in which R1 and R2 are the same or different and are hydrogen or an alkyl group and R3 and R4 are the same or different and wherein the alkyl groups in each case can be 1 to 15 carbon atoms and wherein preferably R1 and R2 are hydrogen and R3 and R4 each are methyl to form an alpha -ketocarboxylic acid amide of general formula (V) (V) and this, in a given case after previous saponification to the free acid, condensed with thiocarbohydrazide to form a 1,2,4-triazin-5-one compound of general formula (VI) (VI) and then the mercapto group is methylated.
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公开(公告)号:CA1041507A
公开(公告)日:1978-10-31
申请号:CA245549
申请日:1976-02-11
Applicant: DEGUSSA
Inventor: HASCHKE HEINZ , SCHREYER GERD , SCHWARZE WERNER , SUCHSLAND HELMUT
IPC: C07D251/42 , C07D251/44 , C07D251/50
Abstract: The present invention provides a process for substituting one chlorine atom by an amino group or for successively substituting two chlorine atoms by identical or different amino groups which comprises reacting at least one amine with a 4 to 60% by weight solution or suspension of the cyanuric chloride in the presence of an acid-binding agent and in an organic solvent which is a mixture ofa) 65 to 85% by weight of at least one member selected from aliphatic hydrocarbons containing 5 to 10 carbon atoms and aromatic hydrocarbons andb) 35 to 15% by weight of at least one ketone containing 3 to 8 carbon atoms.
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公开(公告)号:DD131369A5
公开(公告)日:1978-06-21
申请号:DD19929877
申请日:1977-06-03
Applicant: DEGUSSA
Inventor: KLEEMANN AXEL , KLENK HERBERT , SCHWARZE WERNER
IPC: C07C231/06 , C07C20060101 , C07C67/00 , C07C231/00 , C07C235/72 , C07C235/80 , C07C103/127
Abstract: There are prepared alpha -ketocarboxylic acid amides of the formula (I) where R is hydrogen, R1 and R2 are the same or different, R1 is alkyl of 1 to 18 carbon atoms or haloalkyl, preferably chloroalkyl, of 1 to 18 carbon atoms, and R2 is hydrogen, alkyl of 1 to 18 carbon atoms or haloalkyl, preferably chloroalkyl, of 1 to 18 carbon atoms or together is a cycloalkyl group of 3 to 8 carbon atoms which can be substituted by one or more 1 to 5 carbon atom alkyl groups or by one or more halogen atoms, preferably chlorine atoms, with the proviso that when form a cycloalkyl group then R can also be alkyl of 1 to 5 carbon atoms. The process comprises saponifying an acyl cyanide of the formula (II) in which R, R1 and R2 are as defined above in an organic solvent or mixture of such solvents which is liquid and inert under the reaction conditions, first with gaseous hydrogen chloride and then treating with water at a temperature of about -70 DEG C. to about +70 DEG C. and then isolating the alpha -ketocarboxylic acid amide in conventional manner. Several of the cyclic alpha -ketocarboxylic acid amides are new compounds.
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公开(公告)号:AU8109975A
公开(公告)日:1976-11-18
申请号:AU8109975
申请日:1975-05-13
Applicant: DEGUSSA
Inventor: SCHWARZE WERNER , WOLFF SIEGFRIED
IPC: C07D251/46 , A01N43/66 , A01N43/70 , C07D251/52 , C07D401/12 , C07D401/14 , C07D403/14 , C08K5/43 , C08K5/44 , C08L7/00 , C08L9/00 , C08L21/00 , C08L23/00 , C08L33/00 , C08L33/02 , C08L101/00 , C07D55/12 , C07D55/36
Abstract: There are prepared triazine sulphenimides of the formula X ¦ CO ANGLE PARALLEL R1NNC PARALLEL ¦ ANGLE N-CC-S-N ANGLE Y ANGLE R2NC PARALLEL O in which X is O PARALLEL R3C N ANGLE or -S-N ANGLE Y R4C PARALLEL O R1, R2, R3 and R4 are hydrogen or alkyl with 1 to 4 carbon atoms; Y is -CH2-CH2-; -CH2-CH2-CH2-; -CH(CH3)-CH2-; CH3 ¦ -CH2-CH-CH2- R5 ¦ -C-NH- ¦ R6 (where R5 and R6 are hydrogen, alkyl with 1 to 8 carbon atoms, alkylthioalkyl with a total of 2 to 8 carbon atoms, CH3 -S-, alkoxyalkyl with a total of 2 to 8 carbon atoms, CH3O- or phenyl); or R7OR8 ¦ PARALLEL ¦ -N-C-N- (where R7 and R8 are hydrogen, alkyl with 1 to 8 carbon atoms, allyl or phenyl). The compounds are useful as herbicides and as aids in rubber mixtures.
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公开(公告)号:GB1201577A
公开(公告)日:1970-08-12
申请号:GB5598568
申请日:1968-11-26
Applicant: DEGUSSA
Inventor: WEIGERT WOLFGANG MARIA , BERGMAN ELLIOT , YATES JOHN , SCHWARZE WERNER
IPC: C07D251/54
Abstract: 1,201,577. Substituted s-triazines. DEUTSCHE GOLD - UND SILBER-SCHEIDEANSTALT. 26 Nov., 1968, No. 55985/68. Heading C2C. [Also in Division A5] Substituted s-triazines of the general formula where X is C 1-6 alkoxy, C 1-6 alkylmeroapto, azido or halogen, R 1 and R 2 are the same or different and each represents a hydrogen atom, C 1 _ 6 alkyl or alkenyl optionally substituted by chlorine or hydroxy, cyano, C 1-6 alkoxy or C 1-6 alkylmercapto, R 3 and R 4 are C 1-8 alkyl or alkenyl or aralkyl, or may be attached to one another to form a 5- to 7-membered ring, and one of R 3 and R 4 may represent hydrogen, and R 5 is C 1-6 alkyl, aryl or hydrogen, are prepared by reacting a cyanuric halide with an alkynylamine of formula and a compound of formula HNR 1 R 2 to give a a product where X is halogen, which is optionally further reacted with an alkyl mercaptan in the presence of an acid-binding agent, or with an alkali metal alkoxide or alkali metal azide. The initial reactions are generally carried out in the presence of an acid-binding agent. The products of the invention have herbicidal properties.
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