Organic compounds -- part of the class 532-570 series – Organic compounds – Four or more ring nitrogens in the bicyclo ring system
Patent
1981-08-28
1983-10-18
Waltz, Thomas A.
Organic compounds -- part of the class 532-570 series
Organic compounds
Four or more ring nitrogens in the bicyclo ring system
544167, 546330, 546337, 564 48, 564 49, 564 50, 564 51, 564 52, 564 53, 564 54, 260453RW, 562437, 562439, C07C12719, C07C12717
Patent
active
044106971
DESCRIPTION:
BRIEF SUMMARY
The invention relates to a new process for the preparation of N-aryl-N'-(mono- or disubstituted)-urea derivatives having the general formula (I), ##STR2## wherein Aryl is an optionally substituted phenyl group, and cycloalkyl, alkoxy or phenyl group, or nitrogen-containing heterocyclic group which may contain a further hetero atom, or substituted phenyl group, the other may represent only hydrogen atom or an optionally substituted alkyl or alkoxy group.
The phenyl group represented by "Aryl" may bear as optional substituents preferably one or more halogen atoms, nitro groups(s), lower alkyl group(s), lower alkoxy group(s), trihalo-lower alkyl group(s), lower alkylthio group(s) or a phenoxy group optionally substituted with the groups listed in this paragraph.
R.sup.1 and R.sup.2 may represent as alkyl or alkoxy group preferably a group of 1 to 4 carbon atoms, whereas the cycloalkyl groups represented by R.sup.1 or R.sup.2 contain preferably 5 to 8 carbon atoms. These groups may bear optionally e.g. the following substituents: hydroxy group, carboxy group, alkyl group, alkenyl group, alkynyl group, alkoxy group, phenyl group, substituted phenyl group or heteroaryl group. Of the nitrogen-containing heterocyclic groups represented by R.sup.1 R.sup.2 N-- the morpholino group is preferred.
The compounds of the general formula (I) are biologically active or can be converted into biologically active substances.
Some representatives of the compounds having the general formula (I), such as those wherein Aryl is as defined above, R.sup.1 is hydrogen or an optionally substituted alkyl or cycloalkyl group and R.sup.2 is an optionally substituted alkyl or alkoxy group, exert pesticidal, primarily herbicidal effects (see e.g. R. Wegler: Chemie der Pflanzenschutz- und Schadlingsbekampfungsmittel, Springer Verlag, Berlin-Heidelberg-New York, 1970, pp. 241 to 255). Other compounds of the general formula (I), such as N-(4-nitrophenyl)-N'-(3'-pyridylmethyl)-urea (pyrinuron), can be applied as rodenticidal agents. Further representatives of the compounds having the general formula (I), such as those wherein one of R.sup.1 and R.sup.2 is hydrogen and the other is an optionally substituted phenyl group, are pharmaceutically active or can be applied as intermediates in the preparation of pharmaceutically active agents.
Preferred representatives of the compounds having the general formula (I) are as follows: substance, substance, substance, substance, substance, substance, herbicidal substance, substance, substance, substance, herbicidal substance, substance, substance, substance, substance, bacteriostatic agent, agent, and , an antiseptic agent.
The most widely applied methods for the preparation of the compounds having the general formula (I) are based on the reaction of isocyanates and amine derivatives. According to one of these methods isocyanates of the general formula Aryl--NCO are reacted with amines of the general formula NHR.sup.1 R.sup.2, whereas according to another method isocyanates of the general formula R.sup.1 --NCO and amines of the general formula Aryl--NH.sub.2 are applied as reactants. In this latter method compounds of the general formula (I) wherein R.sup.2 is hydrogen are formed. A general description of these reactions can be found in Houben-Weyl: Methoden der organischen Chemie (Georg Thieme Verlag, Stuttgart, 1952, Vol. VIII, pp. 154-156).
The isocyanates applied as starting substances in the above methods are preapred generally by reacting the appropriate amines with phosgene or by subjecting the appropriate carbamates or urea derivatives to thermal decomposition (see Houben-Weyl: Methoden der organischen Chemie; Georg Thieme Verlag, Stuttgart, 1952, Vol. VIII, pp. 119-128).
It is well known that phosgene is highly detrimental to health, thus reactions utilizing phosgene should be performed under keeping specific security measures. It is a further disadvantage that the reaction involves the formation of hydrochloric acid in great amounts, which is difficult to remove and causes serious corrosion proble
REFERENCES:
patent: 3555086 (1971-01-01), Weis et al.
Crosby et al., JACS 76, pp. 4458-4463, (1954).
Schuller et al., JACS 75, pp. 3425-3428, (1953).
Daroczi Ivan
Galambos Peter
Ormenyi Zoltan
Torok Sandor
Voroshazy Lajos
Reanal Finomvegyszergyar
Waltz Thomas A.
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