http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-919913-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_af99df08b153738cd418446a75d09bfc |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07F9-650905 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07F9-6509 |
| filingDate | 1961-01-23-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1963-02-27-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-919913-A |
| titleOfInvention | O-heterocyclic phosphoramidate and phosphoramidothioate esters and their production |
| abstract | The invention comprises compounds of the formula: R.O.P(:X)(Z)(OY) wherein Y is C1-C5 alkyl, X is oxygen or sulphur, Z is amino or C1-C5 mono- or dialkylamino, and R is 5-pyrazolyl or substituted 5-pyrazolyl radical in which the substituent is selected from C1-C5 alkyl, C1-C5 alkenyl, or phenyl. They may be obtained by an esterification and/or amidation reaction in which the 5-pyrazolyl or substituted pyrazolyl radical is introduced into an appropriate compound containing the phosphorus nucleus before, during or after the introduction of the alkylester and/or the amino or alkylamino group. Suitable methods are:- (1) reacting an alkali metal salt of a suitable 5-pyrazolol (ROH) with an O-C1-C5 alkyl phosphoramidochloridate of the formula Cl.P(:X)(OY)Z the reaction being suitably effected in an inert organic solvent and at from 0 to 120 DEG C.; (2) reacting an alkali metal salt of a 5-pyrazolol (ROH) with a C1-C5 alkyl phosphorodichloridate Y.O.P(:X)(Cl)(Cl) to form an intermediate compound of the formula R.O.P(:X)(OY)Cl and then reacting the latter with ammonia or a C1-C5 alkyl amine to produce the desired product. In the first step of reaction (2) the reactants are preferably employed in substantially equimolecular proportions and preferably at a temperature of from -40 DEG to 50 DEG C. and advantageously in the presence of a solvent such as benzene or methyl isobutyl ketone. In the second step the ammonia or C1-C5 alkyl amine is preferably added in a molecular proportion of 2 : 1 to the intermediate dissolved in an organic solvent at from -20 to 80 DEG C. Several examples are given. The products have pesticidal and herbicidal properties (see Group VI). The alkali metal salts of the 5-pyrazolols used as starting materials may be obtained by reacting an alkali metal hydroxide such as sodium or potassium hydroxide with the corresponding 2-pyrazolin-5-one in a solvent such as benzene at from 35 DEG to 100 DEG C. The 2-pyrazolin-5-one compounds used to form the alkali metal salts of the 5-pyrazolols may be obtained by reacting hydrazine or an appropriately substituted hydrazine with a C1-C4 alkyl ester of a suitable acylcarboxylic acid, e.g. formyl acetic acid, aceto acetic acid, propionyl acetic acid, hexanoyl acetic acid, 2-formyl propionic acid, 2-aceto-4-pentenoic acid, 2-(3-butenoyl)-acetic acid, benzoyl acetic acid, 2-furanyl phenyl acetic acid or 2-acetophenyl acetic acid, the reaction being carried out in water as reaction medium and suitably at from 20 DEG to 80 DEG C.ALSO:A herbicidal or parasiticidal composition comprises as active ingredient a compound of the formula R.O.P(: X)(Z)(O.Y) wherein Y is C1-C5 alkyl, X is oxygen or sulphur, Z is amino or mono- or di-C1-C5 alkylamino, and R is 5-pyrazolyl or a substituted 5-pyrazolyl radical in which the substituents are selected from C1-C5 alkyl, C1-C5 alkenyl, or phenyl (see Group IV (b)). The composition may be in the form of a dust or of an aqueous suspension containing a wetting agent or may be in the form of an oil-in-water emulsion which may contain a wetting, dispersing, or emulsifying agent. |
| priorityDate | 1960-01-25-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
Incoming Links
Total number of triples: 56.