Patent GB-794621-A (GB)
Title: Novel compounds and plant growth regulating compositions containing them
IPC: C07C23/30
Filed: 1956-03-12
Abstract: Plant growth regulant compositions, e.g., for suppressing root growth and stem elongation or regulating flowering, comprise at least one compound of the general formula: <FORM:0794621/I/1> wherein each X represents a halogen atom (preferably chlorine), each Y represents a hydrogen or halogen atom, Ra represents an alkylene or alkenylene group of 1-3 carbon atoms, which may be halogen- or hydroxy-substituted, n is 0 or 1, R and each Rb represent a hydrogen atom or an alkyl group of 1-4 carbon atoms, Rb being absent when a double bond exists between the 2-and 3-positions, and E represents a hydroxy, alkoxy, aminoalkoxy, metalloxy, aryloxy or amino group. These compounds, which tend to suppress cell elongation, may be used in conjunction with compounds having the opposite effect (e.g., naphthalene-acetic acid or 2 : 4-dichlorophenoxyacetic acid).  The compositions may be in the form of solutions in water or organic solvents (especially hydrocarbons of relatively high aromaticity such as benzene, toluene, xylene, ethylbenzene, cumene, isodurene, coal tar fractions, straightrun petroleum distillates, thermally or catalytically cracked hydrocarbon oils or platformates, but including also blends of aromatic with paraffinic or naphthenic hydrocarbons such as refined gas oils, light lubricating oils, refined kerosene or mineral seal oils, fatty oils, oxygenated solvents such as alcohols, ketones, glycols and glycol ethers, and chlorinated solvents), dispersions or emulsions of the active agent in a non-solvent therefor, emulsions of a solution of the active agent in a second immiscible liquid, emulsifiable concentrates containing emulsifying agents which are preferably oil-soluble (e.g., alkaryl sulphonates, sulphates of long chain fatty alcohols, amides such as N-hydroxyalkylamides of long chain fatty acids, alkylaryl polyoxyethylene glycol ethers, sulphonated white oils, sorbitan esters of long chain fatty acids and alkylamide sulphonates), or solids comprising the active agent sorbed on a sorptive solid carrier (e.g., finely divided clay, talc, gypsum, lime or wood flour), and may also contain dispersing or defloculating agents, stickers or wetting agents, Examples describe, inter alia: the effect on the germination of seeds of aqueous emulsions of certain of the acids and their salts and esters produced with the aid of a water-soluble aromatic sulphonate emulsifying agent; and the antagonistic action, in buffered aqueous solution, of 1 :4 : 5 : 6 : 7 : 7-hexachlorobicylo (2 : 2 : 1)-5-heptene-2-acetic acid on the one hand and 2 : 4-dichlorophenoxyacetic acid or 2 : 5-dichlorobenzoic acid on the other hand, on the growth of sections cut from the stems of pea seedlings.ALSO:Compositions useful as defoliating agents and, in higher concentrations, as herbicides, comprise at least one compound of the general formula <FORM:0794621/VI/1> wherein each X represents a halogen atom (preferably chlorine), each Y represents a hydrogen or halogen atom, Ra represents an alkylene or alkenylene group of 1-3 carbon atoms, which may be halogen- or hydroxy-substituted, n is 0 or 1, R and each Rb represent a hydrogen atom or an alkyl group of 1-4 carbon atoms, no Rb being present when a double bond exists between the 2- and 3-positions, and E represents a hydroxy, alkoxy, aminoalkoxy, metalloxy, aryloxy or amino group. These compounds may be used alone or in conjunction with other plant growth regulators (e.g. naphthaleneacetic acid and 2 : 4-dichlorophenoxyacetic acid), insecticides (e.g. D.D.T, endrin, dieldrin, aldrin, chlordane, "Systox" (Registered Trade Mark), methoxychlor, rotenone and pyrethrum) or fungicides (e.g. copper compounds, ferbam and captan).  The compositions may be in the form of solutions in water or organic solvents (especially hydrocarbons of relatively high aromaticity such as benzene, toluene, xylene, ethylbenzene, cumene, isodurene, coal tar fractions, straight-run petroleum distillates, thermally or catalytically cracked hydrocarbon oils or platformates, but including also blends of aromatic with paraffinic or naphthenic hydrocarbons such as refined gas oils, light lubricating oils, refined kerosene or mineral seal oils, fatty oils, oxygenated solvents such as alcohols, ketones, glycols and glycol ethers, and chlorinated solvents), dispersions or emulsions of the active agent in a non-solvent therefor, emulsions of a solution of the active ingredient in a second immiscible liquid, emulsifiable concentrates containing emulsifying agents which are preferably oil-soluble (e.g. alkaryl sulphonates, sulphates of long-chain fatty alcohols, amides such as N-hydroxyalkylamides of long-chain fatty acids, alkylaryl polyoxyethylene glycol ethers, sulphonated white oils, sorbitan esters of long-chain fatty acids and alkylamide sulphonates), or solids comprising the active agent sorbed on a sorptive solid carrier (e.g. finely-divided clay, talc, gypsum, lime or wood flour), and may also contain dispersing or deflocculating agents, stickers or wetting agents. Examples describe inter alia: defoliation of peach trees with emulsions prepared by dissolving certain of the free acids and esters in xylene or acetone, adding diesel oil, and emulsifying the solution in water with the acid of a low molecular weight glycerol-phthalic ester emulsifying agent, or by similarly emulsifying a solution of the active ingredient in a petroleum distillate of 38 per cent aromatics content; the effect of similar emulsions and emulsions of salts and amides in defoliating cotton, walnut, ramie and fruit trees, in killing Bermuda grass and in selectively killing oats sprayed together with cotton seedlings; and defoliating cotton with an emulsion prepared by dissolving 1 : 4 : 5 : 6 : 7 : 7 - hexachlorobicyclo - (2 : 2 : 1) - 5 - heptene - 2 - acetic acid, a sulphonate emulsifying agent and ethylene glycol monobutyl ether in light petroleum distillate and emulsifying the solution in water.