Patent GB-1123487-A (GB)
Title: Novel organic acid derivatives
Inventor: DRABER WILFRIED
IPC: A01N37/00
Filed: 1966-03-04
Abstract: Plants or the soil are treated with a compound of the formula Q-CH=CH-CR=CH-Z where Z is COOH, an alkali, alkaline earth' ammonium or substituted ammonium salt thereof, COOR1 where R1 is optionally substituted alkyl or aryl, COR1, hydroxyalkyl, CN, or CON(R2R3) where R2 and R3 from a ring with the N atom, R is H or alkyl of 1-4 carbon atoms, Q is a group of either of the formulae <FORM:1123487/C1/1> <FORM:1123487/C1/2> R4, R5 and R6 are as R, X is H or OH Y is HO, = O or a semicarbazone thereof or alkoxy and W is OH, alkoxy or acyloxy other than 1-hydroxy - b ,2,6,6, - tetramethyl - 4 - oxo - 2 - cyclohexene - 1 - penta - 2,4 - dienoic acid.  A treating composition may contain a carrier and/or surface active agent.ALSO:The invention comprises compounds of the formula Q-CH=CH-CR=CH-Z where Z is COOH, an alkali, alkaline earth, ammonium or substituted ammonium salt thereof, COOR1 where R1 is optionally substituted alkyl or aryl, COR1, CN, hydroxyalkyl or CON(R2R3) where R2 and R3 form a ring with the N atom, R is H or alkyl of 1-4 carbon atoms, Q is a group of either of the formulae <FORM:1123487/C2/1> <FORM:1123487/C2/2> R4, R5 and R6 are as R, X is H or OH Y is OH, = O or a semicarbazone thereof or alkoxy and W is OH, alkoxy or acyloxy other than 1-hydroxy-b ,2,6,6 - tetramethyl - 4 - oxo - 2 - cyclohexene - 1-penta-2,4-dienoic acid and 5-(p-methoxyphenyl) - 3 - methyl - penta - 2,4 - dienoic acid. Compounds in which Q is derived from cyclohexene may be prepared by treating b ,2,6,6,-tetramethyl - 1,3 - cyclohexadiene - 1 - pentaienoic acid or nitrile with activated oxygen to give an epidioxide which is rearranged with dilute alkali to give an acid or nitrile containing hydroxy and keto groups. Compounds in which Z is an ester, carbamoyl or CN group may be obtained from the acid. Compounds in which Q is derived from benzene may be obtained by reacting 4-acetoxybenzolacetone with an alkali haloacetate under reducing conditions and optionally further reacting the products so formed.ALSO:A composition for treating seeds, to delay or inhibit their germination, comprises an inert solid or liquid carrier and/or a surface-active agent and at least one substituted 1, 3-butadiene of the formula:  Q-CH=CH-CR=CH-Z where Z is COOH or an alkali, alkaline earth, ammonium or substituted ammonium salt thereof, COOR1 or COR1 where R1 is an optionally substituted alkyl or aryl group, hydroxyalkyl, CN or CON (R2R3) where R2 and R3 form a ring with the N atom; R is H or an alkyl group of 1-4 carbon atoms, Q is a group having either of the formulae: <FORM:1123487/A1-A3/1> in which, R4 R5 and R6 are as R, X is H or OH, Y is OH, an oxo group or a semicarbazone thereof, or alkoxy and W is OH, alkoxy or acyloxy.  For example, Q may be a residue of a derivative of 1-hydroxy-B, 2, 6, 6,-tetramethyl-4-oxo-2-cyclohexene-1-penta-cis-2-trans 4-dienoic acid, but not the acid residue.  The liquid carrier may be water. The composition may also comprise an insecticide or fertilizer.ALSO:Compositions for use as herbicides comprise a carrier and/or surface active agent and a compound of the formula:- Q-CH=CH-CR=CH-Z where Z is COOH, an alkali, alkaline earth, ammonium or substituted ammonium salt thereof, COOR1 where R1 is optionally substituted alkyl or aryl, COR1, CN, hydroxyalkyl or CON(R2R3) where R2 and R3 form a ring with the N atom, R is H or alkyl of 1-4 carbon atoms, Q is a group of either of the formulae:- <FORM:1123487/A5-A6/1> <FORM:1123487/A5-A6/2> R4, R5 and R6 are as R, X is H or OH, Y is OH, = O or a semicarbazone thereof or alkoxy and W is OH, alkoxy or acyloxy other than 1-hydroxy - b , 2, 6, 6-tetramethyl-4-oxo-2-cyclohexane-1-penta-2, 4-dienoic acid.