Patent GB-692262-A (GB)
Title: Improvements in or relating to plant response agents and treatment of plants therewith
IPC: A01N43/90
Filed: 1950-03-10
Abstract: 3,6-Endoxo-1,2,3,6-tetrahydro-orthophthalic anhydride is prepared by reacting furan and maleic anhydride in isopropyl ether at 35 DEG  C. When the anhydride is dissolved in aqueous ammonia and autoclaved with hydrogen at 225 p.s.i. in the presence of Raney nickel catalyst, 3,6-endoxohexahydro-orthophthalic acid is formed and may be isolated by crystallization of the acidified filtered hydrogenated mass. Copper and zinc 3,6-endoxohexahydro-orthophthalates are obtained by reacting sodium 3,6-endoxohexahydro-orthophthalate with a soluble copper and zinc salt respectively.  Alkyl ammonium 3,6 - endoxo - 1,2,3,6 - tetrahydrophthalates are obtained by neutralizing a methanol solution of 3,6-endoxo-1,2,3,6-tetrahydrophthalic acid with a monoalkylamine such as methylamine, ethylamine, propylamine, butylamine and octylamine.  The corresponding di- and tri-alkylamines may also be used.ALSO:Plant response agents, e.g. root stimulants comprise a compound which in the presence of water yields the anions of 3, 6-endoxohexahydro-orthophthalic acid or 3, 6-endoxo-1, 2, 3, 6, tetrahydro orthophthalic acid and a finely divided solid or viscous liquid or paste carrier or an emulsifying, dispersing or wetting agent or an humectant.  The compound may be the acid per se, the anhydride or an ionizable salt, e.g. of sodium, potassium, calcium, strontium, magnesium, aluminium, iron, cobalt, nickel, zinc, cadmium, mercury, copper, ammonium, mono-, di-, and trialkylammonium, mono-, di-, and trialkanolammonium and mixed alkylal-kanolammonium which is N- substituted by from 2 to 3 alkyl or alkylol radicals.  The salts may be the acid or neutral salts, and the neutral salts may have different cations. The preparation of 3, 6 endoxo-1, 2, 3, 6 tetrahydroorthophthalic anhydride, 3, 6 endoxo hexahydroorthophthalic acid and alkylammonium 3, 6- endoxo- 1, 2, 3, 6- tetrahydrohydrophthalates is given (see Group IV(b)). The compositions may be in the form of dusts or sprays.  Dusts with finely divided solids e,g, clays such as fullers earth, pyrophyllite, talc, bentonite, kieselguhr and diatomaceous earth; sulphur, volcanic ash, calcium carbonate, lime, lignin, wood flour and powdered wheat, soya-bean, potato and cottonseed. Sprays may be formulated with water or oil.  The oils may be of animal, vegetable or mineral origin e.g. kerosene, fuel oil, lubricating oil, soyabean oil, linseed oil, castor oil, sperm oil and cod liver oil.  Dispersions or emulsions may be prepared with e.g. fatty alcohol sulphates, aliphatic or aromatic sulphonates and alkyl polyglycol ethers or analogous thioethers.  The wetting power of the spray may be enhanced by the addition of further wetting agents and/or humectants such as glycerin, diethylene glycol, ethylene glycol, polyethylene glycols and mixtures of glucose and fructose such as corn syrup.  Many examples are given of compositions suitable for use as herbicides and defoliants.ALSO:Herbicides, defoliants and the like plant response agents comprise a compound which in the presence of water yields the anions of 3,6-endoxohexahydro-orthophthalic acid or 3,6-endoxo-1,2,3,6 tetrahydro orthophthalic acid and a finely divided solid or viscous liquid or paste carrier or an emulsifying, dispersing or wetting agent or an humectant.  The compound may be the acid per se, the anhydride or an ionizable salt e.g. of sodium, potassium, calcium, strontium, magnesium, aluminium, iron, cobalt, nickel, zinc, cadmium, mercury, copper, ammonium, mono-, di-, and trialkylammonium, mono-, di- and trialkanolammonium and mixed alkylalkanolammonium which is N-substituted by from 2 to 3 alkyl or alkylol radicals.  The salts may be the acid or neutral salts, and the neutral salts may have different cations.  The preparation of 3,6 endoxo-1,2,3,6 tetrahydro-orthophthalic anhydride, 3,6 endoxo hexahydro-orthophthalic acid and alkylammonium 3,6-endoxo-1,2,3,6-tetrahydrophthalates is given (see Group IV (b)). The compositions may be in the form of dusts or sprays. Dusts with finely divided solids e.g. clays such as fuller's earth, pyrophyllite, talc, bentonite, kieselguhr and diatomaceous earth; sulphur, volcanic ash, calcium carbonate, lime, lignin, wood flour and powdered wheat, soyabean, potato and cotton-seed. Sprays may be formulated with water or oil.  The oils may be of animal, vegetable or mineral origin e.g. kerosene, fuel oil, lubricating oil, soyabean oil, linseed oil, castor oil, sperm oil and cod liver oil. Dispersions or emulsions may be prepared with e.g. fatty alcohol sulphates, aliphatic or aromatic sulphonates and alkyl polyglycol ethers or analogous thioethers.  The wetting power of the spray may be enhanced by the addition of further wetting agents and/or humectants such as glycerin, diethylene glycol, ethylene glycol, polyethylene glycols and mixtures of glucose and fructose such as corn syrup.  Many examples are given of compositions suitable for use as herbicides and defoliants.