Patent GB-689677-A (GB)
Title: Improvements in plant growth regulants
Filed: 1951-09-28
Abstract: The invention comprises as plant growth regulants monoacylated maleic hydrazides.  The compounds are capable of existing in three tautomeric forms.  They may be made by reacting an alkali metal salt of maleic hydrazide with a halide of the desired acid and the lower derivatives may also be made by heating the hydrazide with an acid anhydride.  Many carboxylic acids are mentioned, e.g. saturated or unsaturated aliphatic mono-acids, substituted aliphatic mono-acids, aromatic or substituted aromatic mono-acids, heterocyclic monoacids, substituted or unsubstituted aliphtic diacids and aromatic di-acids. Representative of many specified products are:-acetyl, acrylyl, caproyl, chloroacetyl, a -naphthylacetyl, b -naphthoxyacetyl, indolebutyryl, 2,4,5-trichlorophenoxyacetyl, benzoyl, anisoyl, salicylyl, furoyl and 2-pyridinecarbonyl maleic hydrazides and amongst dicarboxylic acids specified are oxalic, succinic, fumaric, phthalic, tartaric and glutaric acid.  In examples: (1) and (2) maleic hydrazide is acylated by heating with acetic and propionic anhydrides respectively; the potassium salt of maleic hydrazide is treated in benzene with (3) caproyl, (4) 2-ethyl hexyl, and (5) lauroyl chlorides and in dioxane in (7) with 2,4-dichlorophenoxyacetyl chloride, and in (6) maleic hydrazide in sodium hydroxide is treated with benzoyl chloride.ALSO:Plant growth regulants comprise monoacylated maleic hydrazides and an inert medium.  Many carboxylic acids are mentioned from which the acyl derivative may be derived e.g. saturated or unsaturated aliphatic mono-acids, substituted aliphatic mono-acids, aromatic or substituted aromatic mono - acids, heterocyclic mono - acids and substituted or unsubstituted aliphatic and aromatic di-acids.  Representative of many specified acylated hydrazides are: acetyl, acrylyl, caproyl, chloroacetyl, a  naphthylacteyl b -naphthoxyacetyl, indole-butyryl, 2, 4, 5-trichlorphenoxyacetyl, benzoy, anisoyl, salicylyl, furoyl and 2-pyridinecarbonyl maleic hydrazides.  Inert media mentioned includes mineral silicates, organic liquids, oils, waxes and wax-like solids, and anionic, non-ionic or cationic surface active agents may be present to aid in the formation of aqueous dispersions or emulsions. Solutions in oil or aqueous oil emulsions are generally preferred. Anionic surface agents mentioned are those of formulae RCOOM, RSO3M and ROSO3M where M is an alkali-metal, ammonium or amine radicle and R is an organic radicle containing at least one group of more than 8C atoms e.g. soaps, alkyl sulphates and sulphonates, sulphonated and sulphated ethers of long and short chain aliphatic groups, sulphonated alkyl and glycol esters of long chain fatty acids, sulphonated alkyl substituted amides of long chain fatty acids, alkylated aryl sulphonates, hydro-aromatic sulphonates, alkyl sulphosuccinates and aryl-sulphonate-formaldehyde condensation products.  Non-ionic surface agents mentioned are monoethers and monoesters of polyglycols with long chain fatty alcohols, monoethers of polyglycols with alkylated phenols, partial esters of polyhydric alcohols with long chain mono-carboxylic acids and partial or complete esters of long chain mono-carboxylic acids fatty and/or resin) with polyglycol ethers of polyhydric alcohols.  Cationic surface agents mentioned are quaternary ammonium salts in which one of the groups attached to N has an aliphatic group of at least 8 C atoms and amines, amides, diamines and glyoxalidines having an aliphatic group of at least 8 C atoms and their acid esters.  The regulants function by inhibiting plant growth and by hormone response.  The inhibiting effect is illustrated in examples in which in (8) field corn is treated with a 1/400 aqueous solution of acetyl maleic hydrazide containing an alkyl aryl polythylene glycol (also used as dispersing agent in (9) to (11), and tomatoes are treated in (9) with 10 per cent solutions of caproyl and benzoyl maleic hydrazide in benzene, dibutylphthalate and a hydrocarbon oil which are emulsified with water to dilutions of 1/400 in (10) with 1/400 aqueous dispersions of caproyl maleic hydrazide in hydrocarbon oils and Sun Solvent (an aromatic organic solvent) and with a 1/200 aqueous dispersion or emulsion of 2-ethyl hexoyl maleic hydrazide in hydrocarbon oil and in (12) with 30 per cent formulations of maleic hydrazide and 2-ethyl hexoyl maleic hydrazide in carboroax 1500, hydrogenated glyceride oil, polyoxyethylene sorbitan mono-laurate, lanolin and soybean oil and in (13) pinto beans are treated with a 1/200 aqueous dispersion obtained by agitation of water to which a 30 per cent hydrocarbon oil solution of 2-ethyl hexoyl maleic hydrazide is added.  In the Examples growth and such factors as chlorosis and pigmentation are compared with check treatments with similar solutions but which contain no hydrazide.ALSO:A herbicidal or phytocidal composition comprises a monoacylated maleic hydrazide and an inert medium.  Many carboxylic acids are mentioned from which the aryl derivative may be derived e.g. saturated or unsaturated aliphatic mono-acids, substituted aliphatic mono-acids, aromatic or substituted aromatic mono-acids, heterocyclic mono-acids and substituted or unsubstituted aliphatic and aromatic di-acids. Representative of many specified acylated hydrazides are:-acetyl, acrylyl, capropyl, chloroacetyl, a -naphthylacetyl, b -naphthoxyacetyl, indolebutyryl, 2,4,5-trichlorophenoxyacetyl, benzcyl, aniscyl, salicylyl, furcyl and 2-pyridinecarbonyl maleic hydrazides. Inert media mentioned include mineral silicates, organic liquids, oils, waxes and wax-like solids and anionic, non-ionic or cationic surface-active agents may be present to aid in the formation of aqueous dispersions or emulsions.  Solutions in oil or aqueous oil emulsions are generally preferred.  Anionic surface agents mentioned are those of formulae RCOOM, RSO3M and ROSO3M where M is an alkali-metal, ammonium or amine radicle and R is an organic radicle containing at least one group of more than 8 C atoms e.g. soaps, alkyl sulphates and sulphonates, sulphonated and sulphated ethers of long and short chain aliphatic groups, sulphonated alkyl and glycol esters of long chain fatty acids, sulphonated alkyl substituted amides of long chain fatty acids, alkylated aryl sulphonates, hydroaromatic sulphonates, alkyl sulphosuccinates and aryl sulphonate-formaldehyde condensation products.  Non-ionic surface agents mentioned are monoethers and monoesters of polyglycols with long chain fatty alcohols, monoethers of polyglycols with alkylated phenols, partial esters of polyhydric alcohols with long chain monocarboxylic acids and partial or complete esters of long chain monocarboxylic acids (fatty and/or resin) with polyglycol ethers of polyhydric alcohols.  Cationic surface agents mentioned are quaternary ammonium salts in which one of the groups attached to N has an aliphatic group of at least 8 C atoms and amines, amides, diamines and glyoxalidines having an aliphatic group of at least 8 C atoms and their acid esters.  The herbicidal effect is illustrated in Examples in which in (8) field corn is treated with 1/400 aqueous solution of acetyl maleic hydrazide containing an alkyl aryl polyethylene glycol (also used as dispersing agent in (9) to (11), and tomatoes are treated in (9) with 10 per cent solutions of caproyl and benzoyl maleic hydrazide in benzene, dibutylphthalate and a hydrocarbon oil which are emulsified with water to dilutions of 1/400, in (10) with 1/400 aqueous dispersion of triethanolamine and propionyl maleic hydrazide, in (11) with 1/400 aqueous dispersions of caproyl maleic hydrazide in hydrocarbon oils and Sun Solvent (an aromatic organic solvent) and with an 1/200 aqueous dispersion or emulsion of 2-ethyl hexoyl maleic hydrazide in hydrocarbon oil and in (12) with 30 per cent formulations of maleic hydrazide and 2-ethyl hexoyl maleic hydrazide in carbowax 1,500, hydrogenated glyceride oil, polyoxyethylene sorbitan mono laurate, landin and soybean oil, and in (13) pinto beans are treated with an 1/200 aqueous dispersion obtained by agitation of water to which a 30 per cent hydrocarbon oil solution of 2-ethyl hexoyl maleic hydrazide is added.  In the Examples growth and such factors as chlorosis and pigmentation are compared with check treatments with similar solutions but which contain no hydrazide.