Patent GB-885464-A (GB)
Title: Herbicides and o-ester bis-amides of phosphoric acid for use therein
Inventor: BAKER JOSEPH WILLARD
IPC: C07F9/24
Filed: 1958-04-10
Abstract: Phosphoric acid compounds having the general formula <FORM:0885464/IV (b)/1> in which R is an alkyl, alkenyl or halogenated alkenyl group and each of R1, R2, R3 and R4\h is an alkyl group having 1 to 4 carbon atoms or an alkenyl group having 3 or 4 carbon atoms, e.g. allyl, the total number of carbon atoms being at least 10 but not more than 30 and which are used as active ingredients of herbicidal compositions (see Group VI) may be prepared either by (a) reacting one mole of an alcohol, alkenol or halogenated alkenol with one mole of a phosphoryl halide to form an O-alkyl, O-alkenyl or O-haloalkenyl phosphoryl dihalide which is then reacted with one mole of a secondary amine NHR1R2 and one mole of a secondary amine NHR3R4 and sufficient of the secondary amine should be employed to combine with the hydrogen halide liberated or alternatively anhydrous ammonia may be present as disclosed in Specification 848,952, or (b) by first reacting one mole of a phosphoryl halide with one mole of a secondary amine NHR1R2 and with one mole of a secondary amine NHR3R4 and then reacting the resulting tetra N-substituted diamido phosphoryl monohalide with an alkali metal alkoxide, alkenoxide or halogenated alkenoxide.  In the case of those products in which R is a vinyl or substituted vinyl group an O-alkyl tetra N-substituted diamido phosphite may be reacted with an a -halogenated aldehyde or ketone to form the corresponding O-vinyl tetra N-substituted diamido phosphate having one halogen atom less than that present in the a -halogenated aldehyde or ketone.  The invention also comprises as new compounds those having the above general formula in which (a) R, R1, R2, R3 and R4 are all alkyl groups and R has 7 to 12 carbon atoms, (b) R is a halogenated alkenyl group and at least one of R1, R2, R3 and R4 is an alkyl or alkenyl group having 3 or 4 carbon atoms any remainder being alkyl groups having one or two carbon atoms, and (c) R is an alkyl group having 3 to 6 carbon atoms and each of R1, R2, R3 and R4 is an allyl group the total number of carbon atoms in R, R1, R2, R3 and R4 in each case being at least ten but not more than thirty.  The preferred halogen-substituted alkenyl groups are 2-chlorovinyl and 2,2-dichlorovinyl but the following halogenated alkenyl groups are also mentioned: 2-chloroallyl, 3-chloroallyl, 2-bromoallyl, 2,3-dichloroallyl, 3,3-dichloroallyl, 2-fluoro-3-chloroallyl, 2-bromovinyl, dichlorofluoromethyl-2,2-difluorovinyl, 1-pentyl-2,2-dichlorovinyl and 1-trichloromethyl-2,2-dichlorovinyl. Examples are given for the production of O-ethyl bis (diallylamido) phosphate, O-ethyl bis(di-n-butylamido) phosphate, O-(2-ethylhexyl-, O-n-octyl-, O-n-hexyl-, O-(6-methylheptyl)-, O-n-decyl-, and O-n-dodecyl-bis(dimethylamido)-phosphates, and O-butyl- and O-(2-ethylhexyl)-bis(di-n-propylamido) phosphates.ALSO:A herbicidal composition comprises an O-ester bis-amide of phosphoric acid having the formula <FORM:0885464/VI/1> in which R is an alkyl, alkenyl or halogenated alkenyl group and each of R1, R2, R3 and R4 is a C1-C4 alkyl group or a C3 or C4 alkenyl group, the total number of carbon atoms being at least 10 but not more than 30 together with an inert finely-divided solid or liquid diluent.  The composition may be in a form suitable for spraying, e.g. in the form of an emulsion made by dispersing the active ingredient or an organic solvent solution thereof in water by means of a suitable dispersing agent.  Dry compositions may be made by impregnating an inert finely-divided solid carrier such as talc, a clay, pyrophillite, silica or fuller's earth with the active ingredient and such compositions may be dispersed in water. Specification 848,952 is referred to.