Patent GB-822069-A (GB)
Title: Plant-growth regulants comprising heterocyclic nitrogen compounds
IPC: C07D237/20
Filed: 1956-12-17
Abstract: Diazine compounds used as plant growth regulants (see Groups I and VI) are prepared by the following methods:-  4 - Chloro - 2 : 6 - bis - ethylamino - pyrimidine is made by the action of ethylamine on 2 : 4 : 6-trichloro-pyrimidine.  Similarly 4-chloro-2 : 6-bis - diethylamino - pyrimidine, 4 - methyl - 2 : 6 - bis - ethylamino - pyrimidine, 2 : 3 - bis - ethylamino - quinazoline and 1 : 4 - bis - ethylaminophthalazine are prepared.  2 - Diethylamino - 4 - methyl - pyrimidine is made by the action of diethylamine on 2-chloro-4-methyl-pyrimidine.  Similarly 4-methyl-2 : 6-bis - diethylamino - pyrimidine, 2 - chloro - 3 - ethylamino - quinoxaline, 2 - chloro - 3 - diethylamino - quinoxaline, 2 - diethylamino - quinoxaline, 4 - ethylamino - quinazoline, 4 - diethylaminoquinazoline, 2 - chloro - 4 - ethylamino - quinazoline, 2 - chloro - 4 - diethylaminoquinazoline and 3 : 6 - dichloro - 4 - isopropylamino - pyridazine are prepared.  4 - Chloro - 2 : 6 - bis - ethoxy - pyrimidine is made by the action of sodium ethoxide on 2 : 4 : 6 - trichloro - pyrimidine. Similarly 4 - methyl - 2 : 6 - diethoxy - pyrimidine, 1 - chloro - 4 - alloxy - phthalazine and 1 - bromo - 4 - methoxy - phthalazine are prepared.ALSO:Preparations for influencing, especially inhibiting, plant growth comprise at least one diazine and/or benzodiazine, substituted in the nucleus by one or more halogen atoms, e.g. chlorine, or mono- or di-alkylamino, mono- or di-alkenylamino, alkoxy, alkenyloxy, alkylmercapto, alkenylmercapto, polymethylenimino or morpholino groups and optionally further substituted by an amino group or one or more alkly radicals of 1-4 carbon atoms, in a finely distributable form in association with a carrier which, if it is an organic liquid, boils above 175 DEG C. and which may be inert or may itself be phytotoxic. The nuclear substituent is preferably attached to the diazine ring forming part of the grouping -C(X)=N-N= wherein X is chlorine or an amino, mono- or di-alkylamino, mono- or di-alkenylamino, N-alkenyl-N-alkyl-amino, alkoxy, alkenyloxy, alkylmercapto or alkenylmercapto group.  A large number of substituted pyrimidines, pyridazines, cinnolines, quinazolines, quinoxalines and phthalazines which may be used as active plant growth regulants are specified. The preparations may suitably take the form of (a) solutions in mineral oil fractions, coal tar oils, tetrahydro-naphthalene or alkylated naphthalenes optionally containing auxiliary solvents, e.g. xylene; (b) emulsions containing the active ingredient as such or dissolved in a solvent, emulsified with a wetting or dispersing agent such as a soap, sulphuric ester, long chained aliphatic-aromatic sulphonic acid, long chained alkoxyacetic acid, polyethylene ether of a fatty alcohol or a polyethylene oxide condensate, homogenised in water; (c) dusts containing talc, diatomaceous earth, kaolin bentonite, calcium carbonate, boric acid, tricalcium phosphate, sawdust, powdered cork or coal and (d) pulverulent preparations or pastes made suspendable in water by the addition of wetting agents and protective colloids.  Examples describe (1) a dust comprising 2 : 6-bis-ethylamino-4-chloropyrimidine, 1 - bromo - 4 - methoxy phthalazine or 2-chloro-3-ethylamino-quinoxaline, a carrier, i.e. kaolin or calcium carbonate and carboxymethyl cellulose of polyvinyl alcohol; (2) a wettable powder comprising 2-methyl-mercapto-4-methyl pyrimidine, 2 : 6-bispiperidino-4-chloro-pyrimidine, 2 : 4 : 6-trichlorpyrimidine or 2-chloro-4-ethylaminoquinazoline, carrier i.e. talc or chalk, wetting agent, e.g. alkyl naphthalene sulphonic acid and protective colloid, e.g. sulphite waste liquor; (3) 1-chloro-4-allylmercapto-phthalazine, 2 : 4 : 6-trichloro-pyrimidine, 2 : 6-bis diethylamino-4-chloro-pyrimidine or 4-diethylamino-quinazoline in a solvent, e.g. xylene with an emulsifier, e.g. an ethylene oxide-alkyl phenol condensate, emulsified in water, (4) a solution of 2 : 6-bis-morpholino-4-chloropyrimidine, 2 : 6-bis-ethylamino-4-chloropyrimidine or 4-ethylamino-quinazoline, dissolved in spindle oil; (5) a granulate of, 1-chloro-4-allyloxy-phthalazine, 2 : 4 : 6-triethylmercapto-pyrimidine, 2 : 6-bis-ethylamino-4-chloro-pyrimidine or 2-chloro-4-ethylamino-quinazoline with ammonium sulphate; (6) powders comprising 2 : 4 : 6-trichloro-, 2 : 6-bis-ethylamino-4-methyl-, 2 : 6-diethoxy -4-methyl- or 2-diethylamino-4-methyl-, pyrimidine or 2-chloro-4-methyl-quinoline and talc; (7) a powder comprising 2-chloro-3-ethylamino-quinoxaline and talc; (8) a wettable powder comprising 2 : 6-bis-ethylamino-4-chloro-pyrimdine as in (2) and (9) a spraying composition containing 4-diethylamino-quinazoline, 2-chloro-4-ethylaminoquinazoline or 2-diethylamino-4-methy-6-chloro pyrimidine.ALSO:Preparations for influencing, especially inhibiting, plant growth comprise at least one diazine and/or benzodiazine, substituted in the nucleus by one or more halogen atoms, e.g. chlorine, or mono- or di-alkylamino, mono- or di-alkenylamino, alkoxy, alkenyloxy, alkylmercapto, alkenylmercapto, polymethylenimino or morpholino groups and optionally further substituted by an amino group or one or more alkyl radicals of 1-4 carbon atoms, in a finely-distributable form in association with a carrier which, if it is an organic liquid, boils above 175 DEG  C. and which may be inert or may itself be phytotoxic.  The nuclear substituent is preferably attached to the diazine ring forming part of the grouping -C(X)=N-N= wherein X is chlorine or an amino, mono- or di-alkylamino, mono- or di-alkenylamino, N-alkenyl-N-alkyl-amino, alkoxy, alkenyloxy, alkylmercapto or alkenylmercapto group.  A large number of substituted pyrimidines, pyridazines, cinnolines, quinazolines, quinoxalines and phthalazines which may be used as active plant growth regulants are specified.  The preparations may suitably take the form of (a) solutions in mineral oil fractions, coal tar oils, tetrahydronaphthalene or alkylated naphthalenes, optionally containing auxiliary solvents, e.g. xylene; (b) emulsions containing the active ingredient as such or dissolved in a solvent, emulsified with a wetting or dispersing agent such as a soap, sulphuric ester, long-chained aliphatic-aromatic sulphonic acid, long-chained alkoxyacetic acid, polyethylene ether of a fatty alcohol or a polyethylene ether of a fatty alcohol or a polyethylene oxide condensate, homogenized in water; (c) dusts containing talc, diatomaceous earth, kaolin, bentonite, calcium carbonate, boric acid, tricalcium phosphate, sawdust, powdered cork or coal and (d) pulverulent preparations or pastes made suspendable in water by the addition of wetting agents and protective colloids.  Examples describe (1) a dust comprising 2 : 6-bis-ethylamino-4-chloropyrimidine, 1 - bromo - 4 - methoxy phthalazine or 2-chloro-3-ethylamino-quinoxaline, a carrier, i.e. kaolin or calcium carbonate and carboxymethyl cellulose or polyvinyl alcohol; (2) a wettable powder comprising 2-methylmercapto-4-methyl pyrimidine, 2 : 6-bis-piperidino-4-chloro-pyrimidine, 2 : 4 : 6-trichloropyrimidine or 2-chloro-4-ethylamino-quinazoline, carrier, i.e. talc or chalk, wetting agent, e.g. alkyl naphthalene sulphonic acid and protective colloid, e.g. sulphite waste liquor; (3) 1-chloro-4-4-allylmercapto-phthalazine, 2 : 4 : 6-trichloropyrimidine, 2 : 6 - bis - diethylamino - 4 - chloropyrimidine or 4-diethylamino-quinazoline in a solvent, e.g. xylene with an emulsifier, e.g. an ethylene oxide-alkyl phenol condensate, emulsified in water; (4) a solution of 2 : 6-bis-morpholino - 4 - chloro - pyrimidine, 2 : 6 - bis - ethylamino - 4 - chloro - pyrimidine or 4 - ethylamino-quinazoline, dissolved in spindle oil; (5) a granulate of 1-chloro-4-allyloxy-phthalazine, 2 : 4 : 6 - tri - ethylmercapto - pyrimidine, 2 : 6 - bis - ethylamino - 4 - chloro - pyrimidine or 2-chloro-4-ethylamino-quinazoline with ammonium sulphate; (6) powders comprising 2 : 4 : 6-trichloro-, 2 : 6-bis-ethylamino-4-methyl-, 2 : 6-diethoxy - 4 - methyl - or 2 - diethylamino - 4 - methyl-, pyrimidine or 2-chloro-4-methyl-quinoline and talc; (7) a powder comprising 2-chloro-3-ethylamino-quinoxaline and talc; (8) a wettable powder comprising 2 : 6-bis-ethylamino-4-chloro-pyrimidine as in (2); and (9) a spraying composition containing 4-diethylamino-quinazoline, 2-chloro-4-ethylamino-quinazoline or 2-diethylamino-4-methyl-6-chloropyrimidine.