Method of preparing diurethans

专利摘要:
Diurethanes of the formula <IMAGE> wherein R1 is alkyl, alkenyl or halogenoalkyl and R2 is phenyl or phenyl substituted in one or more places by the same or different substituents selected from the group consisting of halogen, trifluoromethyl, alkyl and alkoxy.
公开号:SU727137A3
申请号:SU772535804
申请日:1977-10-27
公开日:1980-04-05
发明作者:Борошевски Герхард；Арндт Фридрих
申请人:Шеринг Аг (Фирма)；
IPC主号:

专利说明:

The invention relates to a process for the preparation of new chemical compounds, specifically, diurethanes of the general formula O II .1 0-C-NC - "H-YO-0-CH2 where R is alkyl haloethyl or allyl; R2. phenyl, methylphenyl, chlorophenyl, dichlorophenyl trifluoromethylphenyl or cyclohexyl, which have post-herbicidal herbicidal activity, especially in combating difficult-to-eliminate weeds in crops of soybeans. The proposed method is based on the well-known reaction of the preparation of urethanes by the interaction of the esters of chloroic acid and amine 1 and consists in the fact that the ester of chloroformic acid and the propargyl ester of 3-hydroxyphenylcarbamic acid of the formula interaction with an amine of the general formula where R and R 2 are as defined above, in the presence of an acid acceptor, for example, an inorganic base (sodium hydroxide, sodium or potassium carbonates) or an organic base (triethylamine). The amine is usually taken in excess. About potassium carbonate is used as an acid acceptor. The starting materials are known, they can be obtained by known spores.P and Mer. 3- (2-Propynyloxycarbonylamino) -phenyl ester N-isobutyl-L-p-tolylcarbamic acid. In solution 16, 3 g (0.1 mol) of N-isobutyl-p-toluidine in 50 ml of ethyl acetate - are added dropwise over 20 minutes while stirring and cooling to 15c a solution of 25.4 g (0.1 mol) of 3- (2-propynyloxycarbonylamino) phenyl chloroformate in 100 ml of ethyl acetate and at the same time
a solution of 13.8 g (0.1 mol) of potassium carbonate in 50 MP of water. The mixture is stirred at 15 ° C for 30 minutes, the organic phase is separated and spilled with dilute sodium hydroxide solution with dilute hydrochloric acid and water, dried over magnesium sulfate, evaporated under reduced pressure, and the residue is recrystallized from ethyl acetate-pentane.
Yield 27 g (71%). Mp. 10b-107s Calculated,%: C 69.45; H 6.36; N 7.36.
Found,%: C 69.42 N 6.37; N 7.22 ..
Similarly may be
diurethanes were obtained - 3- (2-propynyloxycarbonylamino) -phenyl esters, LK2-carbamic acid; presented in the table.
Table
Continued tables.
Table continuation
Long-term tables

权利要求:
Claims (1)
[1]
Claim
A method of producing diurethanes of the general formula
I "1 ocn <r ₂
НН-С0-0 - <! Н ₂ -С = СН:
enter into the interaction of p amine General formula
00-00 -0-CH ₂ - (! E (} H where is alkyl C ^ -C ^, haloethyl or allyl;
R 2. - phenyl, methylphenyl, chlorine phenyl, dachlorophenyl, trifluoromethylphenyl or cyclohexyl, characterized in that the chloroformate is ester and propar-.
TSNIIIPI Order 691/45 Circulation
Λ
ΗΝ _χ r ₂ where R ^ and Rj. have the above meanings in the presence of an acid acceptor.

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同族专利:

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NZ185554A|1980-05-08|

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BR7707299A|1978-07-25|

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引用文献:

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DE1567151C3|1965-04-09|1974-02-21|Schering Ag, 1000 Berlin Und 4619 Bergkamen|Diurethanes, processes for the preparation of these compounds and herbicidal compositions containing them|

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DE2413933A1|1974-03-20|1975-09-25|Schering Ag|DIURETHANE WITH SELECTIVE HERBICIDAL EFFECT|

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US4202684A|1975-12-18|1980-05-13|Schering Aktiengesellschaft|Carbanilic acid esters, process for making the same and herbicidal compositions containing same|

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DE2557552C2|1975-12-18|1984-12-20|Schering AG, 1000 Berlin und 4709 Bergkamen|Diurethanes and herbicidal agents containing these compounds as active ingredients|DE2901658A1|1979-01-15|1980-07-24|Schering Ag|DIURETHANE, METHOD FOR PRODUCING THESE COMPOUNDS AND HERBICIDES CONTAINING THEM|

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DE2913975A1|1979-04-05|1980-10-23|Schering Ag|N--CARBANILIC ACID--ESTERS, METHOD FOR PRODUCING THESE COMPOUNDS AND THE SELECTIVE HERBICIDES CONTAINING THEM|

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FI93416C|1991-09-27|1995-04-10|Kemira Oy|Process for the preparation of a herbicide product in granular or tablet form|

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US5651975A|1991-09-27|1997-07-29|Harju-Jeanty; Pontus|Method for the preparation of herbicidal granular products comprising two separate phases|

法律状态:

优先权:

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申请号 | 申请日 | 专利标题

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DE19762650796|DE2650796A1|1976-11-03|1976-11-03|DIURETHANE, METHOD FOR PRODUCING THESE COMPOUNDS AND THE SELECTIVE HERBICIDAL PRODUCT CONTAINING THEM|

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